organic compounds
Sulfamerazine tetrahydrofuran monosolvate
aDepartment of Chemistry, University of Dhaka, Dhaka-1000, Bangladesh
*Correspondence e-mail: acsbd@yahoo.com
The title solvate, C11H12N4O2S·C4H8O, crystallizes with three molecules of sulfamerazine [4-amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamide] and three molecules of tetrahydrofuran solvent in the The dihedral angles between the aromatic rings in the sulfamerazine molecules are 83.40 (12), 87.40 (12) and 89.54 (12)°. In the crystal, molecules are linked by N—H⋯O and N—H⋯N hydrogen bonds, generating (10-6) sheets.
Keywords: crystal structure; sulfamerazine; tetrahydrofuran.
CCDC reference: 1473264
Structure description
This is the first Pbca (Acharya et al., 1982), Pna21 (Caria & Mohamed, 1992) and P21/c (Hossain, 2006).
of solvated sulfamerazine. The structure of three polymorphs of sulfamerazine have been published in space groupsThe endocyclic N—C—N angles (pyrimidine ring) of 127.0 (2)–127.5 (2)° in the title compound (Fig. 1) are comparable with the corresponding values in the polymorphs of sulfamerazine; these angles are considerably larger than the value usually observed for a pyrimidine ring.
The planes of the benzene and pyrimidine rings are inclined to each other by 83.40 (12)–89.54 (12)°; these dihedral angles are larger than the corresponding values of 71 (1)° (Acharya et al., 1982), 61.5 (5) and 58.5 (5)° (Caria & Mohamed, 1992) and 64.39 (2)° (Hossain, 2006) in the polymorphs of sulfamerazine. This may be due to the solvation of the tetrahydrofuran molecules hydrogen bonded to the sulfamerazine molecules. The torsion angles of the sulfamerazine molecule in this solvate indicate that the sulfamerazine molecules adopt a gauche conformation when viewed along the S—N vector.
In the crystal, molecules are linked by N—H⋯O and N—H⋯N hydrogen bonds (Table 1), generating (10) sheets.
Synthesis and crystallization
Solid sulfamerazine (0.5446 g, 2 mmol) was dissolved in 50 ml of hot methanol and a methanolic solution of CuCl2·2H2O (0.1705 g, 1 mmol) was added slowly with constant stirring on a hot plate. A red precipitate was formed and stirring was continued six hours. The precipitate was filtered and dried over silica gel. The red precipitate was dissolved in THF solution, filtered and left for crystallization at 273 K. Two weeks later, colorless blocks were filtered and dried over silica gel.
Refinement
Crystal data, data collection and structure . The mosaicity of the diffraction pattern was high and it did not diffract well so the Rint value is high.
details are summarized in Table 2
|
Structural data
CCDC reference: 1473264
10.1107/S2414314616005964/hb4037sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005964/hb4037Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616005964/hb4037Isup3.cml
Solid sulfamerazine (0.5446 g, 2 mmol) was dissolved in 50 ml of hot methanol and a methanolic solution of CuCl2.2H2O (0.1705 g, 1 mmol) was added slowly with constant stirring on a hot plate. A red precipitate was formed and the mixture was continued to stir for six hours. The precipitate was filtered and dried over silica gel. The red precipitate was dissolved in THF solution, filtered and left for crystallization at 273 K. Two weeks later, colorless blocks of (I) were filtered and dried over silica gel.
Crystal data, data collection and structure
details are summarized in Table 1. The H atoms were geometrically placed (C—H = 0.95–0.99 Å, N—H = 0.88–0.90Å) and refined as riding with Uiso(H) = xUeq(C,N) where x = 1.5 for methyl H and 1.2 for all other H. The mosaicity of the diffraction pattern was high and it did not diffract well so the Rint is high. Crystal data, data collection and structure details are summarized in Table 1.Solid sulfamerazine (0.5446 g, 2 mmol) was dissolved in 50 ml of hot methanol and a methanolic solution of CuCl2·2H2O (0.1705 g, 1 mmol) was added slowly with constant stirring on a hot plate. A red precipitate was formed and the mixture was continued to stir for six hours. The precipitate was filtered and dried over silica gel. The red precipitate was dissolved in THF solution, filtered and left for crystallization at 273 K. Two weeks later, colorless blocks were filtered and dried over silica gel.
Crystal data, data collection and structure
details are summarized in Table 2. The mosaicity of the diffraction pattern was high and it did not diffract well so the Rint value is high.This is the first
of solvated sulfamerazine. The structure of three polymorphs of sulfamerazine have been published in space groups Pbca (Acharya et al., 1982), Pna21 (Caria & Mohamed, 1992) and P21/c (Hossain, 2006).The endocyclic N—C—N angles (pyrimidine ring) of 127.0 (2)–127.5 (2)° in the title compound are comparable with the corresponding values in the polymorphs of sulfamerazine; these angles are considerably larger than the value usually observed for a pyrimidine ring.
The planes of the benzene and pyrimidine rings are inclined to each other by 83.40 (12)–89.54 (12)°; these dihedral angles are larger than the corresponding values of 71 (1)° (Acharya et al., 1982), 61.5 (5) and 58.5 (5)° (Caria & Mohamed, 1992) and 64.39 (2)° (Hossain, 2006) in the polymorphs of sulfamerazine. This may be due to the solvation of the tetrahydrofuran molecule hydrogen bonded to the sulfamerazine molecules. The torsion angles of the sulfamerazine molecule in this solvate indicate that the sulfamerazine molecules adopt a
conformation when viewed along the S—N vector.In the crystal, molecules are linked by N—H···O and N—H···N hydrogen bonds (Table 1), generating (106) sheets.
Data collection: COLLECT (Hooft, 1998; Nonius, 2004); cell
(Otwinowski & Minor, 1997); data reduction: (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).Fig. 1. The molecular structure with 30% probability displacement ellipsoids for non-H atoms. |
C11H12N4O2S·C4H8O | F(000) = 2136 |
Mr = 336.41 | Dx = 1.372 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5765 (2) Å | Cell parameters from 10636 reflections |
b = 11.8088 (2) Å | θ = 2.9–27.5° |
c = 39.1512 (7) Å | µ = 0.22 mm−1 |
β = 92.618 (1)° | T = 150 K |
V = 4884.71 (15) Å3 | Block, colorless |
Z = 12 | 0.25 × 0.22 × 0.20 mm |
Nonius KappaCCD diffractometer | 10636 independent reflections |
Radiation source: fine-focus sealed tube | 6070 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.119 |
ω and φ scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | h = −13→13 |
Tmin = 0.947, Tmax = 0.957 | k = −15→12 |
26393 measured reflections | l = −50→50 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.169 | w = 1/[σ2(Fo2) + (0.0684P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
10636 reflections | Δρmax = 0.41 e Å−3 |
625 parameters | Δρmin = −0.58 e Å−3 |
C11H12N4O2S·C4H8O | V = 4884.71 (15) Å3 |
Mr = 336.41 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.5765 (2) Å | µ = 0.22 mm−1 |
b = 11.8088 (2) Å | T = 150 K |
c = 39.1512 (7) Å | 0.25 × 0.22 × 0.20 mm |
β = 92.618 (1)° |
Nonius KappaCCD diffractometer | 10636 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 6070 reflections with I > 2σ(I) |
Tmin = 0.947, Tmax = 0.957 | Rint = 0.119 |
26393 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.41 e Å−3 |
10636 reflections | Δρmin = −0.58 e Å−3 |
625 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S11 | 0.25291 (6) | 0.32196 (6) | 0.86011 (2) | 0.02129 (18) | |
S21 | 0.73980 (6) | 0.65993 (6) | 0.80975 (2) | 0.02120 (18) | |
S31 | 0.74417 (6) | 0.83415 (6) | 0.97168 (2) | 0.02228 (18) | |
O11 | 0.22462 (17) | 0.20954 (15) | 0.87149 (4) | 0.0262 (4) | |
O12 | 0.30284 (17) | 0.33533 (16) | 0.82686 (4) | 0.0284 (5) | |
O21 | 0.78019 (16) | 0.76950 (15) | 0.79868 (4) | 0.0268 (5) | |
O22 | 0.69177 (17) | 0.64950 (16) | 0.84348 (4) | 0.0287 (5) | |
O31 | 0.68851 (17) | 0.85232 (16) | 1.00396 (4) | 0.0292 (5) | |
O32 | 0.77429 (16) | 0.72023 (15) | 0.96177 (4) | 0.0267 (5) | |
N11 | 0.12207 (19) | 0.39811 (19) | 0.85734 (5) | 0.0247 (5) | |
H11 | 0.0974 | 0.4239 | 0.8370 | 0.030* | |
N12 | 0.08098 (19) | 0.37871 (19) | 0.91486 (5) | 0.0218 (5) | |
N13 | −0.0476 (2) | 0.49571 (19) | 0.87746 (5) | 0.0241 (5) | |
N14 | 0.5984 (2) | 0.5253 (2) | 0.96566 (6) | 0.0341 (6) | |
H14A | 0.6044 | 0.4951 | 0.9862 | 0.041* | |
H14B | 0.6432 | 0.5856 | 0.9610 | 0.041* | |
N21 | 0.86047 (19) | 0.5717 (2) | 0.81117 (5) | 0.0257 (6) | |
H21 | 0.8837 | 0.5429 | 0.8312 | 0.031* | |
N22 | 0.89790 (19) | 0.5881 (2) | 0.75340 (5) | 0.0237 (5) | |
N23 | 1.0164 (2) | 0.46017 (19) | 0.78991 (5) | 0.0249 (5) | |
N24 | 0.3689 (2) | 0.4854 (2) | 0.70574 (6) | 0.0393 (7) | |
H24A | 0.3619 | 0.5175 | 0.6855 | 0.047* | |
H24B | 0.3215 | 0.4267 | 0.7104 | 0.047* | |
N31 | 0.87487 (19) | 0.90998 (19) | 0.97536 (5) | 0.0259 (6) | |
H31 | 0.8924 | 0.9426 | 0.9952 | 0.031* | |
N32 | 0.9370 (2) | 0.87305 (19) | 0.92019 (5) | 0.0245 (5) | |
N33 | 1.0552 (2) | 0.9978 (2) | 0.95796 (5) | 0.0272 (6) | |
N34 | 0.4198 (2) | 1.0297 (2) | 0.86005 (6) | 0.0326 (6) | |
H34A | 0.3732 | 1.0900 | 0.8637 | 0.039* | |
H34B | 0.4186 | 0.9985 | 0.8396 | 0.039* | |
C11 | 0.0479 (2) | 0.4246 (2) | 0.88462 (6) | 0.0200 (6) | |
C12 | 0.0132 (2) | 0.4121 (2) | 0.94139 (7) | 0.0254 (7) | |
C13 | −0.0859 (3) | 0.4873 (3) | 0.93699 (7) | 0.0330 (8) | |
H13 | −0.1335 | 0.5111 | 0.9557 | 0.040* | |
C14 | −0.1132 (3) | 0.5264 (3) | 0.90433 (7) | 0.0336 (8) | |
H14 | −0.1818 | 0.5776 | 0.9007 | 0.040* | |
C15 | 0.3542 (2) | 0.3840 (2) | 0.89128 (6) | 0.0205 (6) | |
C16 | 0.4259 (2) | 0.4786 (2) | 0.88334 (7) | 0.0240 (6) | |
H16 | 0.4186 | 0.5109 | 0.8611 | 0.029* | |
C17 | 0.5076 (2) | 0.5252 (2) | 0.90798 (7) | 0.0264 (7) | |
H17 | 0.5564 | 0.5898 | 0.9026 | 0.032* | |
C18 | 0.5193 (2) | 0.4785 (2) | 0.94098 (7) | 0.0237 (6) | |
C19 | 0.4475 (2) | 0.3824 (2) | 0.94814 (7) | 0.0230 (6) | |
H19 | 0.4558 | 0.3487 | 0.9702 | 0.028* | |
C20 | 0.3653 (2) | 0.3361 (2) | 0.92385 (6) | 0.0212 (6) | |
H20 | 0.3162 | 0.2717 | 0.9292 | 0.025* | |
C21 | 0.9280 (2) | 0.5395 (2) | 0.78351 (6) | 0.0200 (6) | |
C22 | 0.9583 (2) | 0.5492 (2) | 0.72655 (7) | 0.0258 (7) | |
C23 | 1.0500 (3) | 0.4662 (3) | 0.73016 (7) | 0.0320 (7) | |
H23 | 1.0931 | 0.4390 | 0.7110 | 0.038* | |
C24 | 1.0766 (3) | 0.4242 (3) | 0.76258 (7) | 0.0315 (7) | |
H24 | 1.1400 | 0.3677 | 0.7656 | 0.038* | |
C25 | 0.6292 (2) | 0.6087 (2) | 0.77938 (6) | 0.0203 (6) | |
C26 | 0.6176 (2) | 0.6598 (2) | 0.74717 (6) | 0.0220 (6) | |
H26 | 0.6705 | 0.7219 | 0.7420 | 0.026* | |
C27 | 0.5298 (2) | 0.6203 (2) | 0.72295 (7) | 0.0253 (6) | |
H27 | 0.5209 | 0.6567 | 0.7013 | 0.030* | |
C28 | 0.4536 (2) | 0.5268 (2) | 0.73002 (7) | 0.0249 (6) | |
C29 | 0.4649 (2) | 0.4768 (2) | 0.76266 (7) | 0.0279 (7) | |
H29 | 0.4119 | 0.4150 | 0.7680 | 0.034* | |
C30 | 0.5528 (2) | 0.5174 (2) | 0.78696 (7) | 0.0252 (6) | |
H30 | 0.5608 | 0.4827 | 0.8088 | 0.030* | |
C31 | 0.9596 (2) | 0.9269 (2) | 0.94987 (6) | 0.0223 (6) | |
C32 | 1.0181 (3) | 0.8950 (2) | 0.89552 (7) | 0.0278 (7) | |
C33 | 1.1182 (3) | 0.9691 (3) | 0.90116 (7) | 0.0339 (7) | |
H33 | 1.1749 | 0.9852 | 0.8837 | 0.041* | |
C34 | 1.1330 (3) | 1.0185 (3) | 0.93276 (7) | 0.0349 (8) | |
H34 | 1.2015 | 1.0695 | 0.9369 | 0.042* | |
C35 | 0.6488 (2) | 0.8931 (2) | 0.93866 (6) | 0.0209 (6) | |
C36 | 0.5742 (2) | 0.9872 (2) | 0.94514 (7) | 0.0263 (7) | |
H36 | 0.5759 | 1.0200 | 0.9673 | 0.032* | |
C37 | 0.4979 (2) | 1.0324 (2) | 0.91911 (7) | 0.0271 (7) | |
H37 | 0.4472 | 1.0968 | 0.9234 | 0.032* | |
C38 | 0.4941 (2) | 0.9845 (2) | 0.88630 (7) | 0.0233 (6) | |
C39 | 0.5698 (2) | 0.8894 (2) | 0.88041 (7) | 0.0225 (6) | |
H39 | 0.5679 | 0.8558 | 0.8583 | 0.027* | |
C40 | 0.6465 (2) | 0.8445 (2) | 0.90619 (7) | 0.0223 (6) | |
H40 | 0.6978 | 0.7805 | 0.9019 | 0.027* | |
C56 | 0.0545 (3) | 0.3624 (3) | 0.97532 (6) | 0.0351 (8) | |
H56A | 0.1384 | 0.3917 | 0.9823 | 0.053* | |
H56B | 0.0583 | 0.2797 | 0.9734 | 0.053* | |
H56C | −0.0062 | 0.3832 | 0.9924 | 0.053* | |
C57 | 0.9215 (3) | 0.6026 (3) | 0.69277 (7) | 0.0390 (8) | |
H57A | 0.9127 | 0.6846 | 0.6957 | 0.059* | |
H57B | 0.8407 | 0.5709 | 0.6841 | 0.059* | |
H57C | 0.9870 | 0.5872 | 0.6765 | 0.059* | |
C58 | 0.9911 (3) | 0.8349 (3) | 0.86235 (7) | 0.0419 (9) | |
H58A | 0.9073 | 0.8571 | 0.8529 | 0.063* | |
H58B | 0.9931 | 0.7529 | 0.8662 | 0.063* | |
H58C | 1.0554 | 0.8555 | 0.8462 | 0.063* | |
O41 | 0.75615 (19) | 0.36623 (19) | 1.01187 (5) | 0.0414 (6) | |
O42 | 0.2191 (2) | 0.6315 (2) | 0.65606 (6) | 0.0490 (6) | |
O43 | 0.3115 (2) | 0.84734 (18) | 0.81484 (6) | 0.0484 (6) | |
C41 | 0.7635 (3) | 0.3445 (3) | 1.04792 (8) | 0.0408 (8) | |
H41A | 0.7407 | 0.4131 | 1.0608 | 0.049* | |
H41B | 0.8501 | 0.3209 | 1.0555 | 0.049* | |
C42 | 0.6696 (3) | 0.2502 (3) | 1.05346 (8) | 0.0472 (9) | |
H42A | 0.5870 | 0.2811 | 1.0598 | 0.057* | |
H42B | 0.7016 | 0.1981 | 1.0717 | 0.057* | |
C43 | 0.6576 (3) | 0.1892 (3) | 1.01893 (8) | 0.0383 (8) | |
H43A | 0.6858 | 0.1095 | 1.0211 | 0.046* | |
H43B | 0.5692 | 0.1908 | 1.0095 | 0.046* | |
C44 | 0.7442 (3) | 0.2564 (3) | 0.99650 (8) | 0.0444 (9) | |
H44A | 0.8279 | 0.2193 | 0.9957 | 0.053* | |
H44B | 0.7069 | 0.2623 | 0.9729 | 0.053* | |
C45 | 0.2034 (3) | 0.6474 (3) | 0.61990 (9) | 0.0538 (10) | |
H45A | 0.1132 | 0.6609 | 0.6133 | 0.065* | |
H45B | 0.2324 | 0.5795 | 0.6077 | 0.065* | |
C46 | 0.2823 (4) | 0.7491 (3) | 0.61114 (9) | 0.0549 (10) | |
H46A | 0.2335 | 0.8017 | 0.5959 | 0.066* | |
H46B | 0.3599 | 0.7257 | 0.5998 | 0.066* | |
C47 | 0.3146 (3) | 0.8040 (3) | 0.64550 (8) | 0.0460 (9) | |
H47A | 0.4052 | 0.7935 | 0.6522 | 0.055* | |
H47B | 0.2952 | 0.8860 | 0.6449 | 0.055* | |
C48 | 0.2318 (3) | 0.7430 (3) | 0.66945 (9) | 0.0500 (9) | |
H48A | 0.2715 | 0.7415 | 0.6928 | 0.060* | |
H48B | 0.1482 | 0.7803 | 0.6702 | 0.060* | |
C49 | 0.3219 (3) | 0.7412 (3) | 0.83223 (9) | 0.0458 (9) | |
H49A | 0.2973 | 0.7492 | 0.8562 | 0.055* | |
H49B | 0.4099 | 0.7126 | 0.8322 | 0.055* | |
C50 | 0.2324 (3) | 0.6605 (3) | 0.81282 (8) | 0.0390 (8) | |
H50A | 0.1538 | 0.6489 | 0.8252 | 0.047* | |
H50B | 0.2732 | 0.5862 | 0.8093 | 0.047* | |
C51 | 0.2048 (3) | 0.7208 (3) | 0.77892 (8) | 0.0482 (9) | |
H51A | 0.2204 | 0.6700 | 0.7594 | 0.058* | |
H51B | 0.1159 | 0.7471 | 0.7770 | 0.058* | |
C52 | 0.2948 (3) | 0.8194 (3) | 0.77967 (8) | 0.0448 (9) | |
H52A | 0.3764 | 0.7979 | 0.7701 | 0.054* | |
H52B | 0.2584 | 0.8841 | 0.7665 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S11 | 0.0219 (4) | 0.0264 (4) | 0.0156 (3) | 0.0045 (3) | 0.0009 (3) | −0.0011 (3) |
S21 | 0.0205 (4) | 0.0252 (4) | 0.0177 (4) | 0.0036 (3) | −0.0004 (3) | −0.0016 (3) |
S31 | 0.0202 (4) | 0.0277 (4) | 0.0187 (4) | −0.0072 (3) | −0.0011 (3) | 0.0012 (3) |
O11 | 0.0297 (11) | 0.0252 (11) | 0.0233 (10) | 0.0034 (9) | −0.0043 (8) | −0.0012 (8) |
O12 | 0.0301 (11) | 0.0396 (13) | 0.0158 (10) | 0.0056 (9) | 0.0058 (8) | −0.0009 (8) |
O21 | 0.0274 (10) | 0.0243 (11) | 0.0281 (11) | −0.0002 (9) | −0.0062 (8) | 0.0018 (8) |
O22 | 0.0297 (11) | 0.0396 (13) | 0.0170 (10) | 0.0075 (9) | 0.0042 (8) | −0.0020 (8) |
O31 | 0.0264 (11) | 0.0451 (13) | 0.0163 (10) | −0.0120 (10) | 0.0027 (8) | 0.0018 (9) |
O32 | 0.0277 (10) | 0.0265 (12) | 0.0254 (11) | −0.0049 (9) | −0.0058 (8) | 0.0028 (8) |
N11 | 0.0234 (12) | 0.0352 (15) | 0.0153 (12) | 0.0082 (11) | 0.0003 (9) | 0.0033 (10) |
N12 | 0.0189 (12) | 0.0307 (14) | 0.0158 (12) | 0.0014 (10) | 0.0008 (9) | 0.0031 (10) |
N13 | 0.0239 (12) | 0.0310 (14) | 0.0175 (12) | 0.0067 (11) | 0.0008 (9) | 0.0038 (10) |
N14 | 0.0338 (14) | 0.0362 (16) | 0.0319 (14) | −0.0113 (12) | −0.0025 (11) | −0.0015 (11) |
N21 | 0.0227 (12) | 0.0367 (15) | 0.0173 (12) | 0.0098 (11) | −0.0023 (9) | 0.0064 (10) |
N22 | 0.0211 (12) | 0.0346 (15) | 0.0156 (12) | 0.0039 (11) | 0.0018 (9) | 0.0030 (10) |
N23 | 0.0240 (12) | 0.0329 (15) | 0.0179 (12) | 0.0079 (11) | 0.0005 (9) | 0.0002 (10) |
N24 | 0.0384 (15) | 0.0485 (18) | 0.0305 (15) | −0.0172 (13) | −0.0051 (12) | −0.0003 (12) |
N31 | 0.0220 (12) | 0.0370 (15) | 0.0187 (12) | −0.0103 (11) | 0.0010 (9) | −0.0049 (10) |
N32 | 0.0222 (12) | 0.0344 (15) | 0.0168 (12) | −0.0044 (11) | −0.0003 (9) | −0.0016 (10) |
N33 | 0.0246 (12) | 0.0380 (15) | 0.0191 (13) | −0.0137 (11) | 0.0013 (10) | −0.0030 (10) |
N34 | 0.0346 (14) | 0.0367 (15) | 0.0263 (14) | 0.0110 (12) | −0.0017 (11) | 0.0044 (11) |
C11 | 0.0186 (13) | 0.0267 (16) | 0.0146 (14) | −0.0012 (12) | −0.0007 (10) | −0.0015 (11) |
C12 | 0.0207 (14) | 0.0381 (18) | 0.0173 (14) | −0.0009 (13) | 0.0012 (11) | −0.0010 (12) |
C13 | 0.0306 (16) | 0.050 (2) | 0.0184 (15) | 0.0117 (15) | 0.0030 (12) | −0.0041 (13) |
C14 | 0.0295 (16) | 0.045 (2) | 0.0266 (17) | 0.0152 (15) | 0.0021 (13) | 0.0008 (14) |
C15 | 0.0187 (14) | 0.0221 (15) | 0.0209 (14) | 0.0045 (12) | 0.0041 (11) | −0.0029 (11) |
C16 | 0.0246 (15) | 0.0255 (16) | 0.0223 (15) | 0.0047 (13) | 0.0048 (12) | 0.0026 (12) |
C17 | 0.0264 (15) | 0.0237 (16) | 0.0296 (16) | −0.0037 (13) | 0.0070 (12) | 0.0020 (12) |
C18 | 0.0181 (14) | 0.0316 (17) | 0.0215 (15) | 0.0006 (13) | 0.0028 (11) | −0.0045 (12) |
C19 | 0.0217 (14) | 0.0275 (16) | 0.0197 (14) | 0.0000 (12) | 0.0003 (11) | 0.0022 (12) |
C20 | 0.0197 (14) | 0.0224 (15) | 0.0216 (15) | 0.0020 (12) | 0.0019 (11) | 0.0006 (11) |
C21 | 0.0165 (13) | 0.0280 (16) | 0.0155 (14) | 0.0016 (12) | 0.0002 (10) | 0.0011 (11) |
C22 | 0.0208 (14) | 0.0369 (18) | 0.0196 (15) | 0.0012 (13) | 0.0003 (11) | 0.0008 (13) |
C23 | 0.0311 (16) | 0.048 (2) | 0.0168 (15) | 0.0102 (15) | 0.0049 (12) | −0.0028 (13) |
C24 | 0.0292 (16) | 0.0389 (19) | 0.0264 (17) | 0.0117 (14) | 0.0009 (13) | −0.0022 (14) |
C25 | 0.0193 (14) | 0.0220 (15) | 0.0198 (14) | 0.0029 (12) | 0.0041 (11) | 0.0004 (11) |
C26 | 0.0223 (14) | 0.0212 (15) | 0.0226 (15) | 0.0011 (12) | 0.0005 (11) | 0.0000 (11) |
C27 | 0.0256 (15) | 0.0283 (17) | 0.0218 (15) | −0.0004 (13) | −0.0004 (12) | 0.0011 (12) |
C28 | 0.0210 (14) | 0.0303 (17) | 0.0231 (15) | −0.0015 (13) | 0.0001 (11) | −0.0064 (12) |
C29 | 0.0264 (15) | 0.0262 (17) | 0.0317 (17) | −0.0064 (13) | 0.0072 (12) | 0.0009 (13) |
C30 | 0.0267 (15) | 0.0279 (17) | 0.0212 (15) | 0.0032 (13) | 0.0040 (12) | 0.0036 (12) |
C31 | 0.0211 (14) | 0.0300 (17) | 0.0159 (14) | −0.0023 (12) | 0.0002 (11) | 0.0024 (12) |
C32 | 0.0289 (16) | 0.0345 (18) | 0.0202 (15) | −0.0019 (14) | 0.0016 (12) | 0.0014 (12) |
C33 | 0.0320 (17) | 0.048 (2) | 0.0223 (16) | −0.0113 (15) | 0.0063 (12) | −0.0003 (14) |
C34 | 0.0311 (17) | 0.048 (2) | 0.0260 (17) | −0.0194 (15) | 0.0070 (13) | −0.0046 (14) |
C35 | 0.0200 (14) | 0.0246 (16) | 0.0183 (14) | −0.0065 (12) | 0.0012 (11) | 0.0007 (11) |
C36 | 0.0267 (15) | 0.0276 (17) | 0.0250 (16) | −0.0047 (13) | 0.0058 (12) | −0.0038 (12) |
C37 | 0.0268 (15) | 0.0249 (16) | 0.0299 (17) | 0.0029 (13) | 0.0054 (12) | −0.0026 (12) |
C38 | 0.0191 (14) | 0.0269 (16) | 0.0238 (15) | −0.0006 (12) | 0.0000 (11) | 0.0058 (12) |
C39 | 0.0201 (14) | 0.0267 (16) | 0.0207 (14) | −0.0006 (12) | 0.0004 (11) | −0.0017 (12) |
C40 | 0.0194 (14) | 0.0238 (16) | 0.0236 (15) | −0.0007 (12) | 0.0010 (11) | −0.0003 (12) |
C56 | 0.0315 (17) | 0.055 (2) | 0.0188 (16) | 0.0075 (16) | 0.0040 (12) | 0.0061 (14) |
C57 | 0.0411 (19) | 0.058 (2) | 0.0182 (16) | 0.0153 (17) | 0.0023 (13) | 0.0070 (14) |
C58 | 0.051 (2) | 0.055 (2) | 0.0209 (17) | −0.0154 (18) | 0.0092 (14) | −0.0115 (15) |
O41 | 0.0397 (13) | 0.0418 (14) | 0.0435 (14) | −0.0011 (11) | 0.0088 (10) | 0.0051 (11) |
O42 | 0.0471 (14) | 0.0436 (15) | 0.0571 (16) | 0.0022 (12) | 0.0099 (11) | 0.0111 (12) |
O43 | 0.0591 (16) | 0.0386 (14) | 0.0471 (15) | −0.0102 (12) | −0.0034 (12) | −0.0045 (11) |
C41 | 0.0356 (19) | 0.047 (2) | 0.039 (2) | 0.0022 (16) | −0.0001 (15) | −0.0040 (16) |
C42 | 0.064 (2) | 0.037 (2) | 0.041 (2) | −0.0001 (18) | 0.0180 (17) | −0.0022 (15) |
C43 | 0.0362 (18) | 0.041 (2) | 0.0378 (19) | −0.0004 (16) | 0.0049 (14) | 0.0029 (15) |
C44 | 0.0406 (19) | 0.053 (2) | 0.040 (2) | −0.0023 (17) | 0.0086 (15) | −0.0059 (17) |
C45 | 0.049 (2) | 0.053 (3) | 0.058 (3) | 0.012 (2) | −0.0105 (18) | −0.0118 (19) |
C46 | 0.080 (3) | 0.040 (2) | 0.045 (2) | 0.009 (2) | 0.0156 (19) | 0.0022 (17) |
C47 | 0.0361 (19) | 0.051 (2) | 0.051 (2) | 0.0009 (17) | 0.0007 (16) | −0.0005 (17) |
C48 | 0.053 (2) | 0.058 (3) | 0.040 (2) | 0.0099 (19) | 0.0065 (17) | 0.0012 (18) |
C49 | 0.052 (2) | 0.039 (2) | 0.046 (2) | −0.0055 (18) | −0.0035 (16) | 0.0034 (17) |
C50 | 0.0393 (19) | 0.036 (2) | 0.042 (2) | −0.0022 (15) | 0.0063 (15) | −0.0017 (15) |
C51 | 0.049 (2) | 0.048 (2) | 0.046 (2) | −0.0012 (18) | −0.0072 (17) | −0.0008 (17) |
C52 | 0.044 (2) | 0.044 (2) | 0.047 (2) | 0.0001 (17) | 0.0059 (16) | 0.0026 (17) |
S11—O11 | 1.4361 (19) | C29—C30 | 1.386 (3) |
S11—O12 | 1.4359 (19) | C29—H29 | 0.9500 |
S11—N11 | 1.650 (2) | C30—H30 | 0.9500 |
S11—C15 | 1.747 (3) | C32—C33 | 1.384 (4) |
S21—O21 | 1.4358 (19) | C32—C58 | 1.495 (4) |
S21—O22 | 1.4417 (19) | C33—C34 | 1.370 (4) |
S21—N21 | 1.646 (2) | C33—H33 | 0.9500 |
S21—C25 | 1.738 (3) | C34—H34 | 0.9500 |
S31—O31 | 1.4346 (19) | C35—C36 | 1.393 (4) |
S31—O32 | 1.440 (2) | C35—C40 | 1.394 (3) |
S31—N31 | 1.648 (2) | C36—C37 | 1.378 (3) |
S31—C35 | 1.748 (2) | C36—H36 | 0.9500 |
N11—C11 | 1.390 (3) | C37—C38 | 1.403 (3) |
N11—H11 | 0.8800 | C37—H37 | 0.9500 |
N12—C11 | 1.334 (3) | C38—C39 | 1.404 (4) |
N12—C12 | 1.348 (3) | C39—C40 | 1.372 (3) |
N13—C11 | 1.333 (3) | C39—H39 | 0.9500 |
N13—C14 | 1.337 (3) | C40—H40 | 0.9500 |
N14—C18 | 1.365 (3) | C56—H56A | 0.9800 |
N14—H14A | 0.8800 | C56—H56B | 0.9800 |
N14—H14B | 0.8800 | C56—H56C | 0.9800 |
N21—C21 | 1.378 (3) | C57—H57A | 0.9800 |
N21—H21 | 0.8800 | C57—H57B | 0.9800 |
N22—C21 | 1.336 (3) | C57—H57C | 0.9800 |
N22—C22 | 1.336 (3) | C58—H58A | 0.9800 |
N23—C24 | 1.339 (3) | C58—H58B | 0.9800 |
N23—C21 | 1.339 (3) | C58—H58C | 0.9800 |
N24—C28 | 1.366 (3) | O41—C41 | 1.433 (3) |
N24—H24A | 0.8800 | O41—C44 | 1.433 (4) |
N24—H24B | 0.8800 | O42—C48 | 1.422 (4) |
N31—C31 | 1.386 (3) | O42—C45 | 1.430 (4) |
N31—H31 | 0.8800 | O43—C52 | 1.419 (3) |
N32—C31 | 1.337 (3) | O43—C49 | 1.429 (4) |
N32—C32 | 1.346 (3) | C41—C42 | 1.515 (4) |
N33—C34 | 1.336 (3) | C41—H41A | 0.9900 |
N33—C31 | 1.339 (3) | C41—H41B | 0.9900 |
N34—C38 | 1.373 (3) | C42—C43 | 1.532 (4) |
N34—H34A | 0.8800 | C42—H42A | 0.9900 |
N34—H34B | 0.8800 | C42—H42B | 0.9900 |
C12—C13 | 1.378 (4) | C43—C44 | 1.520 (4) |
C12—C56 | 1.499 (3) | C43—H43A | 0.9900 |
C13—C14 | 1.378 (4) | C43—H43B | 0.9900 |
C13—H13 | 0.9500 | C44—H44A | 0.9900 |
C14—H14 | 0.9500 | C44—H44B | 0.9900 |
C15—C16 | 1.394 (4) | C45—C46 | 1.511 (5) |
C15—C20 | 1.395 (3) | C45—H45A | 0.9900 |
C16—C17 | 1.379 (3) | C45—H45B | 0.9900 |
C16—H16 | 0.9500 | C46—C47 | 1.518 (4) |
C17—C18 | 1.405 (4) | C46—H46A | 0.9900 |
C17—H17 | 0.9500 | C46—H46B | 0.9900 |
C18—C19 | 1.401 (4) | C47—C48 | 1.496 (4) |
C19—C20 | 1.372 (3) | C47—H47A | 0.9900 |
C19—H19 | 0.9500 | C47—H47B | 0.9900 |
C20—H20 | 0.9500 | C48—H48A | 0.9900 |
C22—C23 | 1.382 (4) | C48—H48B | 0.9900 |
C22—C57 | 1.500 (3) | C49—C50 | 1.521 (4) |
C23—C24 | 1.379 (3) | C49—H49A | 0.9900 |
C23—H23 | 0.9500 | C49—H49B | 0.9900 |
C24—H24 | 0.9500 | C50—C51 | 1.522 (4) |
C25—C30 | 1.387 (4) | C50—H50A | 0.9900 |
C25—C26 | 1.398 (3) | C50—H50B | 0.9900 |
C26—C27 | 1.378 (3) | C51—C52 | 1.504 (4) |
C26—H26 | 0.9500 | C51—H51A | 0.9900 |
C27—C28 | 1.403 (4) | C51—H51B | 0.9900 |
C27—H27 | 0.9500 | C52—H52A | 0.9900 |
C28—C29 | 1.407 (4) | C52—H52B | 0.9900 |
O11—S11—O12 | 118.25 (11) | C33—C34—H34 | 118.7 |
O11—S11—N11 | 109.77 (12) | C36—C35—C40 | 120.5 (2) |
O12—S11—N11 | 102.86 (11) | C36—C35—S31 | 119.7 (2) |
O12—S11—C15 | 110.37 (12) | C40—C35—S31 | 119.7 (2) |
O11—S11—C15 | 107.49 (12) | C37—C36—C35 | 119.5 (3) |
N11—S11—C15 | 107.65 (12) | C37—C36—H36 | 120.3 |
O21—S21—O22 | 118.40 (11) | C35—C36—H36 | 120.3 |
O21—S21—N21 | 109.83 (12) | C36—C37—C38 | 120.8 (3) |
O22—S21—N21 | 102.72 (11) | C36—C37—H37 | 119.6 |
O21—S21—C25 | 107.90 (12) | C38—C37—H37 | 119.6 |
O22—S21—C25 | 110.03 (12) | N34—C38—C37 | 121.3 (3) |
N21—S21—C25 | 107.43 (12) | N34—C38—C39 | 120.0 (2) |
O31—S31—O32 | 118.81 (12) | C37—C38—C39 | 118.7 (2) |
O31—S31—N31 | 102.59 (11) | C40—C39—C38 | 120.7 (2) |
O32—S31—N31 | 109.65 (12) | C40—C39—H39 | 119.7 |
O31—S31—C35 | 110.23 (12) | C38—C39—H39 | 119.7 |
O32—S31—C35 | 107.49 (12) | C39—C40—C35 | 119.8 (3) |
N31—S31—C35 | 107.56 (12) | C39—C40—H40 | 120.1 |
C11—N11—S11 | 125.00 (17) | C35—C40—H40 | 120.1 |
C11—N11—H11 | 117.5 | C12—C56—H56A | 109.5 |
S11—N11—H11 | 117.5 | C12—C56—H56B | 109.5 |
C11—N12—C12 | 116.0 (2) | H56A—C56—H56B | 109.5 |
C11—N13—C14 | 114.9 (2) | C12—C56—H56C | 109.5 |
C18—N14—H14A | 120.0 | H56A—C56—H56C | 109.5 |
C18—N14—H14B | 120.0 | H56B—C56—H56C | 109.5 |
H14A—N14—H14B | 120.0 | C22—C57—H57A | 109.5 |
C21—N21—S21 | 125.26 (17) | C22—C57—H57B | 109.5 |
C21—N21—H21 | 117.4 | H57A—C57—H57B | 109.5 |
S21—N21—H21 | 117.4 | C22—C57—H57C | 109.5 |
C21—N22—C22 | 116.3 (2) | H57A—C57—H57C | 109.5 |
C24—N23—C21 | 115.2 (2) | H57B—C57—H57C | 109.5 |
C28—N24—H24A | 120.0 | C32—C58—H58A | 109.5 |
C28—N24—H24B | 120.0 | C32—C58—H58B | 109.5 |
H24A—N24—H24B | 120.0 | H58A—C58—H58B | 109.5 |
C31—N31—S31 | 125.66 (18) | C32—C58—H58C | 109.5 |
C31—N31—H31 | 117.2 | H58A—C58—H58C | 109.5 |
S31—N31—H31 | 117.2 | H58B—C58—H58C | 109.5 |
C31—N32—C32 | 116.0 (2) | C41—O41—C44 | 104.6 (2) |
C34—N33—C31 | 115.1 (2) | C48—O42—C45 | 104.3 (2) |
C38—N34—H34A | 120.0 | C52—O43—C49 | 105.2 (2) |
C38—N34—H34B | 120.0 | O41—C41—C42 | 105.4 (2) |
H34A—N34—H34B | 120.0 | O41—C41—H41A | 110.7 |
N12—C11—N13 | 127.5 (2) | C42—C41—H41A | 110.7 |
N13—C11—N11 | 115.4 (2) | O41—C41—H41B | 110.7 |
N12—C11—N11 | 117.1 (2) | C42—C41—H41B | 110.7 |
N12—C12—C13 | 121.4 (2) | H41A—C41—H41B | 108.8 |
N12—C12—C56 | 115.1 (2) | C41—C42—C43 | 104.4 (3) |
C13—C12—C56 | 123.5 (3) | C41—C42—H42A | 110.9 |
C14—C13—C12 | 117.2 (3) | C43—C42—H42A | 110.9 |
C14—C13—H13 | 121.4 | C41—C42—H42B | 110.9 |
C12—C13—H13 | 121.4 | C43—C42—H42B | 110.9 |
N13—C14—C13 | 123.0 (3) | H42A—C42—H42B | 108.9 |
N13—C14—H14 | 118.5 | C44—C43—C42 | 103.7 (3) |
C13—C14—H14 | 118.5 | C44—C43—H43A | 111.0 |
C16—C15—C20 | 120.3 (2) | C42—C43—H43A | 111.0 |
C16—C15—S11 | 120.2 (2) | C44—C43—H43B | 111.0 |
C20—C15—S11 | 119.5 (2) | C42—C43—H43B | 111.0 |
C17—C16—C15 | 119.6 (2) | H43A—C43—H43B | 109.0 |
C17—C16—H16 | 120.2 | O41—C44—C43 | 105.9 (3) |
C15—C16—H16 | 120.2 | O41—C44—H44A | 110.6 |
C16—C17—C18 | 120.8 (3) | C43—C44—H44A | 110.6 |
C16—C17—H17 | 119.6 | O41—C44—H44B | 110.6 |
C18—C17—H17 | 119.6 | C43—C44—H44B | 110.6 |
N14—C18—C19 | 120.4 (2) | H44A—C44—H44B | 108.7 |
N14—C18—C17 | 121.1 (3) | O42—C45—C46 | 106.8 (3) |
C19—C18—C17 | 118.4 (2) | O42—C45—H45A | 110.4 |
C20—C19—C18 | 121.1 (2) | C46—C45—H45A | 110.4 |
C20—C19—H19 | 119.5 | O42—C45—H45B | 110.4 |
C18—C19—H19 | 119.5 | C46—C45—H45B | 110.4 |
C19—C20—C15 | 119.8 (3) | H45A—C45—H45B | 108.6 |
C19—C20—H20 | 120.1 | C45—C46—C47 | 104.0 (3) |
C15—C20—H20 | 120.1 | C45—C46—H46A | 110.9 |
N22—C21—N23 | 127.0 (2) | C47—C46—H46A | 110.9 |
N22—C21—N21 | 117.6 (2) | C45—C46—H46B | 110.9 |
N23—C21—N21 | 115.4 (2) | C47—C46—H46B | 110.9 |
N22—C22—C23 | 121.4 (2) | H46A—C46—H46B | 109.0 |
N22—C22—C57 | 115.8 (2) | C48—C47—C46 | 103.6 (3) |
C23—C22—C57 | 122.8 (3) | C48—C47—H47A | 111.0 |
C24—C23—C22 | 117.5 (3) | C46—C47—H47A | 111.0 |
C24—C23—H23 | 121.3 | C48—C47—H47B | 111.0 |
C22—C23—H23 | 121.3 | C46—C47—H47B | 111.0 |
N23—C24—C23 | 122.5 (3) | H47A—C47—H47B | 109.0 |
N23—C24—H24 | 118.8 | O42—C48—C47 | 105.2 (3) |
C23—C24—H24 | 118.8 | O42—C48—H48A | 110.7 |
C30—C25—C26 | 120.0 (2) | C47—C48—H48A | 110.7 |
C30—C25—S21 | 120.3 (2) | O42—C48—H48B | 110.7 |
C26—C25—S21 | 119.7 (2) | C47—C48—H48B | 110.7 |
C27—C26—C25 | 120.2 (3) | H48A—C48—H48B | 108.8 |
C27—C26—H26 | 119.9 | O43—C49—C50 | 106.2 (2) |
C25—C26—H26 | 119.9 | O43—C49—H49A | 110.5 |
C26—C27—C28 | 120.4 (2) | C50—C49—H49A | 110.5 |
C26—C27—H27 | 119.8 | O43—C49—H49B | 110.5 |
C28—C27—H27 | 119.8 | C50—C49—H49B | 110.5 |
N24—C28—C27 | 120.6 (3) | H49A—C49—H49B | 108.7 |
N24—C28—C29 | 120.5 (3) | C49—C50—C51 | 103.5 (3) |
C27—C28—C29 | 118.9 (2) | C49—C50—H50A | 111.1 |
C30—C29—C28 | 120.3 (3) | C51—C50—H50A | 111.1 |
C30—C29—H29 | 119.8 | C49—C50—H50B | 111.1 |
C28—C29—H29 | 119.8 | C51—C50—H50B | 111.1 |
C29—C30—C25 | 120.1 (2) | H50A—C50—H50B | 109.0 |
C29—C30—H30 | 120.0 | C52—C51—C50 | 104.4 (2) |
C25—C30—H30 | 120.0 | C52—C51—H51A | 110.9 |
N32—C31—N33 | 127.3 (2) | C50—C51—H51A | 110.9 |
N32—C31—N31 | 117.5 (2) | C52—C51—H51B | 110.9 |
N33—C31—N31 | 115.2 (2) | C50—C51—H51B | 110.9 |
N32—C32—C33 | 121.0 (3) | H51A—C51—H51B | 108.9 |
N32—C32—C58 | 115.5 (2) | O43—C52—C51 | 104.5 (3) |
C33—C32—C58 | 123.6 (3) | O43—C52—H52A | 110.9 |
C34—C33—C32 | 117.9 (3) | C51—C52—H52A | 110.9 |
C34—C33—H33 | 121.0 | O43—C52—H52B | 110.9 |
C32—C33—H33 | 121.0 | C51—C52—H52B | 110.9 |
N33—C34—C33 | 122.7 (3) | H52A—C52—H52B | 108.9 |
N33—C34—H34 | 118.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14B···O32 | 0.88 | 2.11 | 2.968 (3) | 166 |
N14—H14A···O41 | 0.88 | 2.40 | 3.051 (3) | 131 |
N24—H24A···O42 | 0.88 | 2.29 | 2.998 (3) | 137 |
N34—H34B···O43 | 0.88 | 2.30 | 2.983 (3) | 134 |
N11—H11···N23i | 0.88 | 2.04 | 2.913 (3) | 169 |
N21—H21···N13ii | 0.88 | 2.00 | 2.873 (3) | 172 |
N24—H24B···O21iii | 0.88 | 2.17 | 2.999 (3) | 158 |
N31—H31···N33iv | 0.88 | 2.02 | 2.893 (3) | 174 |
N34—H34A···O11v | 0.88 | 2.15 | 3.009 (3) | 167 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+2, −y+2, −z+2; (v) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14B···O32 | 0.88 | 2.11 | 2.968 (3) | 166 |
N14—H14A···O41 | 0.88 | 2.40 | 3.051 (3) | 131 |
N24—H24A···O42 | 0.88 | 2.29 | 2.998 (3) | 137 |
N34—H34B···O43 | 0.88 | 2.30 | 2.983 (3) | 134 |
N11—H11···N23i | 0.88 | 2.04 | 2.913 (3) | 169 |
N21—H21···N13ii | 0.88 | 2.00 | 2.873 (3) | 172 |
N24—H24B···O21iii | 0.88 | 2.17 | 2.999 (3) | 158 |
N31—H31···N33iv | 0.88 | 2.02 | 2.893 (3) | 174 |
N34—H34A···O11v | 0.88 | 2.15 | 3.009 (3) | 167 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+2, −y+2, −z+2; (v) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C11H12N4O2S·C4H8O |
Mr | 336.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 10.5765 (2), 11.8088 (2), 39.1512 (7) |
β (°) | 92.618 (1) |
V (Å3) | 4884.71 (15) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.25 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.947, 0.957 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 26393, 10636, 6070 |
Rint | 0.119 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.169, 1.01 |
No. of reflections | 10636 |
No. of parameters | 625 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.41, −0.58 |
Computer programs: COLLECT (Hooft, 1998; Nonius, 2004), (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012).
Acknowledgements
The author acknowledges the School of Chemistry, Cardiff University, Wales, for the data collection.
References
Acharya, K. R., Kuchela, K. N. & Kartha, G. (1982). J. Crystallogr. Spectrosc. Res. 12, 369–376. CAS Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Caria, M. R. & Mohamed, R. (1992). Acta Cryst. B48, 492–498. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Hossain, G. M. G. (2006). Acta Cryst. E62, o2166–o2167. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
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