organic compounds
N-{2-[2-(5-Methyl-1H-pyrazol-3-yl)acetamido]phenyl}benzamide monohydrate
aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and cLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Imouzzer, BP 2202, Fez, Morocco
*Correspondence e-mail: chkiratekarim@gmail.com
The 19H18N4O2·H2O, comprises the U-shaped pyrazole derivative and a solvent water molecule. The molecular conformation is partly determined by an intramolecular N—H⋯O hydrogen bond. The crystal packing is directed by an extensive network of O—H⋯O, N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds together with C—H⋯π(ring) contacts that generate a three-dimensional network.
of the title compound, CKeywords: crystal structure; hydrogen bond; pyrazole.
CCDC reference: 1532509
Structure description
Pyrazole derivatives have pharmacologically attractive biological applications (Havrylyuk et al., 2016) and interesting therapeutic properties (Khan et al., 2016). These compounds have been synthesized as target structures by many researchers and have been evaluated for their beneficial bioactivity and for the rational design of a new generation of small molecule drugs (Küçükgüzel & Şenkardeş, 2015). Continuing our research in this field (Chkirate et al., 2001), we have synthesized N-2-benzamido-phenyl-5-methyl-pyrazol-3-yl acetamide by reacting benzoyl chloride with N-2-aminophenyl-5-methyl-pyrazol-3-yl acetamide. The latter was obtained by the action of hydrazine on the 4-(oxopropylidene)-1,5-benzodiazepin-2-one (El Abbassi et al., 1989).
The title molecule adopts a U-shaped conformation due, in part, to the intramolecular N1—H1⋯O2 hydrogen bond (Table 1 and Fig. 1). The dihedral angle between the C1–C6 and C8–C13 benzene rings is 49.67 (5)° while that between the latter ring and the pyrazole ring is 64.49 (6)°. The packing is governed largely by a network of intermolecular hydrogen bonds including N2—H2A⋯N3i, N4—H4A⋯O3ii, O3—H3A⋯O1, O3—H3B⋯O2iv and C12—H12⋯O3iii (Table 1 and Fig. 2). In addition there are two C—H⋯π(ring) interactions: C15—H15A⋯π(C8–C13)v and C19—H19A⋯π(N3,N4,C16–C18)vi, Table 1, that also contribute to the crystal packing. These contacts combine to generate a three-dimensional network, Fig. 2.
Synthesis and crystallization
To a solution of 5 × 10−4 mol of N-(2-aminophenyl-5-methyl-pyrazol-3-yl)acetamide dissolved in 10 ml of ethanol was added 5 × 10−4 mol of benzoyl chloride. The mixture was stirred for 24 h at room temperature. After filtration and recrystallization from ethanol, colourless single crystals were obtained with a yield of 66%.
Refinement
Crystal and . Eleven reflections appearing near the top of the frames on which they were recorded were omitted from the fineal as they appeared to have been partially obscured by the nozzle of the low-temperature attachment.
details appear in Table 2
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Structural data
CCDC reference: 1532509
https://doi.org/10.1107/S2414314617002516/sj4090sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002516/sj4090Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617002516/sj4090Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617002516/sj4090Isup4.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C19H18N4O2·H2O | Z = 2 |
Mr = 352.39 | F(000) = 372 |
Triclinic, P1 | Dx = 1.304 Mg m−3 |
a = 8.4220 (3) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 10.0410 (4) Å | Cell parameters from 5496 reflections |
c = 10.8799 (4) Å | θ = 4.5–71.9° |
α = 101.889 (2)° | µ = 0.74 mm−1 |
β = 94.104 (2)° | T = 150 K |
γ = 90.402 (1)° | Block, colourless |
V = 897.79 (6) Å3 | 0.15 × 0.14 × 0.10 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 3279 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 2846 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.028 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.2°, θmin = 4.2° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −11→12 |
Tmin = 0.85, Tmax = 0.93 | l = −12→13 |
6831 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | All H-atom parameters refined |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0641P)2 + 0.2007P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3279 reflections | Δρmax = 0.20 e Å−3 |
316 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0164 (16) |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.79721 (16) | 0.27601 (13) | 0.44040 (10) | 0.0459 (3) | |
O2 | 0.93031 (11) | 0.56110 (10) | 0.87382 (10) | 0.0299 (3) | |
N1 | 0.83593 (16) | 0.38781 (15) | 0.64465 (12) | 0.0344 (3) | |
H1 | 0.828 (3) | 0.468 (2) | 0.695 (2) | 0.053 (6)* | |
N2 | 0.77023 (13) | 0.38862 (11) | 0.89936 (10) | 0.0226 (3) | |
H2A | 0.693 (2) | 0.3631 (18) | 0.9497 (18) | 0.037 (5)* | |
N3 | 0.47391 (14) | 0.69851 (11) | 0.95462 (11) | 0.0266 (3) | |
N4 | 0.42223 (14) | 0.79751 (12) | 0.89372 (11) | 0.0275 (3) | |
H4A | 0.315 (3) | 0.798 (2) | 0.870 (2) | 0.050 (6)* | |
C1 | 0.73450 (18) | 0.51188 (18) | 0.48918 (14) | 0.0354 (4) | |
C2 | 0.7643 (2) | 0.63951 (19) | 0.56712 (16) | 0.0421 (4) | |
H2 | 0.830 (2) | 0.651 (2) | 0.648 (2) | 0.050 (5)* | |
C3 | 0.7021 (2) | 0.7553 (2) | 0.53373 (19) | 0.0514 (5) | |
H3 | 0.725 (3) | 0.844 (3) | 0.588 (2) | 0.067 (7)* | |
C4 | 0.6082 (2) | 0.7447 (2) | 0.42178 (19) | 0.0541 (5) | |
H4 | 0.569 (3) | 0.827 (2) | 0.402 (2) | 0.062 (6)* | |
C5 | 0.5786 (2) | 0.6188 (2) | 0.34362 (17) | 0.0499 (5) | |
H5 | 0.509 (3) | 0.608 (2) | 0.264 (2) | 0.055 (6)* | |
C6 | 0.6409 (2) | 0.5025 (2) | 0.37623 (15) | 0.0433 (4) | |
H6 | 0.619 (3) | 0.408 (2) | 0.321 (2) | 0.055 (6)* | |
C7 | 0.79287 (18) | 0.38224 (17) | 0.52099 (14) | 0.0352 (4) | |
C8 | 0.88775 (17) | 0.27928 (15) | 0.70092 (13) | 0.0308 (3) | |
C9 | 0.9735 (2) | 0.17147 (18) | 0.63698 (16) | 0.0416 (4) | |
H9 | 0.996 (3) | 0.177 (2) | 0.552 (2) | 0.057 (6)* | |
C10 | 1.0224 (2) | 0.06677 (18) | 0.69444 (16) | 0.0411 (4) | |
H10 | 1.082 (2) | −0.006 (2) | 0.646 (2) | 0.051 (6)* | |
C11 | 0.98655 (19) | 0.06710 (15) | 0.81653 (15) | 0.0348 (3) | |
H11 | 1.020 (2) | −0.006 (2) | 0.858 (2) | 0.050 (6)* | |
C12 | 0.90333 (17) | 0.17445 (14) | 0.88159 (14) | 0.0280 (3) | |
H12 | 0.880 (2) | 0.1783 (17) | 0.9689 (18) | 0.033 (4)* | |
C13 | 0.85463 (15) | 0.28126 (13) | 0.82543 (13) | 0.0247 (3) | |
C14 | 0.82037 (15) | 0.51951 (13) | 0.92651 (12) | 0.0230 (3) | |
C15 | 0.73064 (17) | 0.61472 (13) | 1.02316 (13) | 0.0254 (3) | |
H15A | 0.810 (2) | 0.6650 (18) | 1.0828 (18) | 0.035 (4)* | |
H15B | 0.664 (2) | 0.5616 (18) | 1.0653 (17) | 0.032 (4)* | |
C16 | 0.63237 (16) | 0.71090 (13) | 0.96200 (13) | 0.0251 (3) | |
C17 | 0.68045 (17) | 0.81614 (14) | 0.90528 (15) | 0.0305 (3) | |
H17 | 0.793 (2) | 0.8410 (19) | 0.8959 (18) | 0.039 (5)* | |
C18 | 0.54213 (17) | 0.86907 (14) | 0.86181 (14) | 0.0279 (3) | |
C19 | 0.5098 (2) | 0.98073 (17) | 0.79240 (18) | 0.0390 (4) | |
H19A | 0.445 (3) | 1.052 (3) | 0.838 (3) | 0.079 (8)* | |
H19B | 0.609 (3) | 1.019 (2) | 0.772 (2) | 0.064 (7)* | |
H19C | 0.445 (3) | 0.947 (2) | 0.714 (2) | 0.052 (6)* | |
O3 | 0.89511 (12) | 0.24005 (10) | 0.20075 (10) | 0.0295 (3) | |
H3A | 0.872 (3) | 0.263 (3) | 0.278 (3) | 0.074 (8)* | |
H3B | 0.946 (3) | 0.315 (3) | 0.181 (2) | 0.061 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0582 (7) | 0.0541 (7) | 0.0246 (6) | 0.0020 (6) | 0.0032 (5) | 0.0061 (5) |
O2 | 0.0293 (5) | 0.0313 (5) | 0.0310 (5) | −0.0026 (4) | 0.0063 (4) | 0.0097 (4) |
N1 | 0.0403 (7) | 0.0429 (7) | 0.0214 (6) | 0.0066 (6) | 0.0041 (5) | 0.0091 (5) |
N2 | 0.0248 (5) | 0.0240 (5) | 0.0202 (5) | 0.0007 (4) | 0.0042 (4) | 0.0061 (4) |
N3 | 0.0275 (6) | 0.0259 (6) | 0.0275 (6) | 0.0019 (4) | 0.0033 (5) | 0.0074 (4) |
N4 | 0.0265 (6) | 0.0270 (6) | 0.0303 (6) | 0.0021 (5) | 0.0022 (5) | 0.0090 (5) |
C1 | 0.0303 (7) | 0.0556 (10) | 0.0240 (7) | −0.0008 (7) | 0.0050 (6) | 0.0156 (6) |
C2 | 0.0413 (9) | 0.0539 (10) | 0.0349 (9) | −0.0047 (7) | −0.0044 (7) | 0.0203 (7) |
C3 | 0.0563 (11) | 0.0548 (11) | 0.0477 (11) | −0.0014 (9) | 0.0004 (9) | 0.0228 (9) |
C4 | 0.0508 (11) | 0.0746 (14) | 0.0483 (11) | 0.0143 (10) | 0.0088 (9) | 0.0368 (10) |
C5 | 0.0385 (9) | 0.0839 (14) | 0.0327 (9) | 0.0126 (9) | 0.0027 (7) | 0.0245 (9) |
C6 | 0.0357 (8) | 0.0713 (12) | 0.0251 (8) | 0.0046 (8) | 0.0028 (6) | 0.0151 (7) |
C7 | 0.0323 (7) | 0.0530 (9) | 0.0217 (7) | −0.0005 (7) | 0.0055 (6) | 0.0099 (6) |
C8 | 0.0311 (7) | 0.0371 (8) | 0.0245 (7) | 0.0046 (6) | 0.0032 (6) | 0.0069 (6) |
C9 | 0.0448 (9) | 0.0514 (10) | 0.0279 (8) | 0.0117 (8) | 0.0096 (7) | 0.0041 (7) |
C10 | 0.0412 (8) | 0.0415 (9) | 0.0370 (9) | 0.0115 (7) | 0.0082 (7) | −0.0023 (7) |
C11 | 0.0359 (8) | 0.0288 (7) | 0.0389 (8) | 0.0034 (6) | 0.0042 (7) | 0.0047 (6) |
C12 | 0.0297 (7) | 0.0266 (7) | 0.0279 (7) | −0.0002 (5) | 0.0041 (6) | 0.0055 (5) |
C13 | 0.0237 (6) | 0.0267 (6) | 0.0226 (7) | 0.0000 (5) | 0.0023 (5) | 0.0026 (5) |
C14 | 0.0241 (6) | 0.0264 (6) | 0.0200 (6) | 0.0016 (5) | −0.0007 (5) | 0.0089 (5) |
C15 | 0.0297 (7) | 0.0237 (6) | 0.0234 (7) | 0.0021 (5) | 0.0023 (6) | 0.0063 (5) |
C16 | 0.0276 (6) | 0.0218 (6) | 0.0253 (7) | 0.0007 (5) | 0.0016 (5) | 0.0036 (5) |
C17 | 0.0275 (7) | 0.0279 (7) | 0.0386 (8) | −0.0009 (6) | 0.0015 (6) | 0.0128 (6) |
C18 | 0.0307 (7) | 0.0240 (6) | 0.0297 (7) | −0.0011 (5) | 0.0024 (6) | 0.0071 (5) |
C19 | 0.0421 (9) | 0.0328 (8) | 0.0464 (10) | 0.0036 (7) | −0.0005 (8) | 0.0191 (7) |
O3 | 0.0316 (5) | 0.0291 (5) | 0.0289 (6) | −0.0006 (4) | 0.0034 (4) | 0.0082 (4) |
O1—C7 | 1.236 (2) | C8—C9 | 1.397 (2) |
O2—C14 | 1.2368 (16) | C8—C13 | 1.399 (2) |
N1—C7 | 1.3578 (19) | C9—C10 | 1.380 (3) |
N1—C8 | 1.413 (2) | C9—H9 | 0.97 (2) |
N1—H1 | 0.88 (2) | C10—C11 | 1.382 (2) |
N2—C14 | 1.3444 (17) | C10—H10 | 0.97 (2) |
N2—C13 | 1.4316 (17) | C11—C12 | 1.386 (2) |
N2—H2A | 0.95 (2) | C11—H11 | 0.98 (2) |
N3—C16 | 1.3346 (18) | C12—C13 | 1.390 (2) |
N3—N4 | 1.3611 (16) | C12—H12 | 0.978 (19) |
N4—C18 | 1.3414 (19) | C14—C15 | 1.5167 (18) |
N4—H4A | 0.92 (2) | C15—C16 | 1.5026 (19) |
C1—C2 | 1.393 (3) | C15—H15A | 0.957 (19) |
C1—C6 | 1.398 (2) | C15—H15B | 0.972 (19) |
C1—C7 | 1.492 (2) | C16—C17 | 1.400 (2) |
C2—C3 | 1.383 (3) | C17—C18 | 1.377 (2) |
C2—H2 | 0.99 (2) | C17—H17 | 0.997 (19) |
C3—C4 | 1.388 (3) | C18—C19 | 1.492 (2) |
C3—H3 | 0.97 (3) | C19—H19A | 0.98 (3) |
C4—C5 | 1.380 (3) | C19—H19B | 0.97 (3) |
C4—H4 | 0.96 (2) | C19—H19C | 0.98 (2) |
C5—C6 | 1.385 (3) | O3—H3A | 0.87 (3) |
C5—H5 | 1.00 (2) | O3—H3B | 0.94 (3) |
C6—H6 | 1.02 (2) | ||
C7—N1—C8 | 127.23 (14) | C9—C10—C11 | 120.29 (14) |
C7—N1—H1 | 115.9 (14) | C9—C10—H10 | 117.5 (13) |
C8—N1—H1 | 116.9 (14) | C11—C10—H10 | 122.2 (13) |
C14—N2—C13 | 123.60 (11) | C10—C11—C12 | 119.52 (15) |
C14—N2—H2A | 117.1 (11) | C10—C11—H11 | 121.3 (12) |
C13—N2—H2A | 117.0 (11) | C12—C11—H11 | 119.2 (12) |
C16—N3—N4 | 104.44 (11) | C11—C12—C13 | 120.87 (14) |
C18—N4—N3 | 112.75 (11) | C11—C12—H12 | 121.0 (10) |
C18—N4—H4A | 129.2 (13) | C13—C12—H12 | 118.1 (10) |
N3—N4—H4A | 117.3 (13) | C12—C13—C8 | 119.56 (13) |
C2—C1—C6 | 118.94 (16) | C12—C13—N2 | 117.38 (12) |
C2—C1—C7 | 123.71 (14) | C8—C13—N2 | 123.06 (13) |
C6—C1—C7 | 117.33 (16) | O2—C14—N2 | 122.29 (12) |
C3—C2—C1 | 120.71 (16) | O2—C14—C15 | 121.70 (12) |
C3—C2—H2 | 117.6 (12) | N2—C14—C15 | 115.99 (12) |
C1—C2—H2 | 121.7 (12) | C16—C15—C14 | 110.76 (11) |
C2—C3—C4 | 119.9 (2) | C16—C15—H15A | 109.7 (11) |
C2—C3—H3 | 120.2 (15) | C14—C15—H15A | 106.3 (11) |
C4—C3—H3 | 119.9 (15) | C16—C15—H15B | 110.7 (10) |
C5—C4—C3 | 119.85 (19) | C14—C15—H15B | 109.5 (10) |
C5—C4—H4 | 123.0 (15) | H15A—C15—H15B | 109.7 (15) |
C3—C4—H4 | 117.1 (15) | N3—C16—C17 | 110.92 (12) |
C4—C5—C6 | 120.57 (16) | N3—C16—C15 | 119.15 (12) |
C4—C5—H5 | 121.4 (12) | C17—C16—C15 | 129.92 (13) |
C6—C5—H5 | 118.0 (13) | C18—C17—C16 | 105.70 (13) |
C5—C6—C1 | 120.03 (18) | C18—C17—H17 | 129.2 (11) |
C5—C6—H6 | 121.8 (12) | C16—C17—H17 | 125.0 (11) |
C1—C6—H6 | 118.1 (13) | N4—C18—C17 | 106.19 (12) |
O1—C7—N1 | 122.37 (16) | N4—C18—C19 | 120.86 (13) |
O1—C7—C1 | 122.02 (14) | C17—C18—C19 | 132.95 (14) |
N1—C7—C1 | 115.58 (14) | C18—C19—H19A | 112.3 (16) |
C9—C8—C13 | 118.99 (14) | C18—C19—H19B | 110.6 (14) |
C9—C8—N1 | 122.09 (14) | H19A—C19—H19B | 111 (2) |
C13—C8—N1 | 118.91 (13) | C18—C19—H19C | 110.7 (12) |
C10—C9—C8 | 120.75 (15) | H19A—C19—H19C | 104 (2) |
C10—C9—H9 | 123.7 (13) | H19B—C19—H19C | 108.2 (19) |
C8—C9—H9 | 115.5 (13) | H3A—O3—H3B | 107 (2) |
C16—N3—N4—C18 | 0.84 (15) | C11—C12—C13—C8 | 1.1 (2) |
C6—C1—C2—C3 | 0.1 (3) | C11—C12—C13—N2 | −179.58 (13) |
C7—C1—C2—C3 | −177.84 (16) | C9—C8—C13—C12 | −1.9 (2) |
C1—C2—C3—C4 | 0.3 (3) | N1—C8—C13—C12 | 179.30 (13) |
C2—C3—C4—C5 | −0.6 (3) | C9—C8—C13—N2 | 178.78 (14) |
C3—C4—C5—C6 | 0.4 (3) | N1—C8—C13—N2 | 0.0 (2) |
C4—C5—C6—C1 | 0.1 (3) | C14—N2—C13—C12 | 120.82 (14) |
C2—C1—C6—C5 | −0.4 (2) | C14—N2—C13—C8 | −59.84 (18) |
C7—C1—C6—C5 | 177.75 (15) | C13—N2—C14—O2 | 11.49 (19) |
C8—N1—C7—O1 | −1.2 (3) | C13—N2—C14—C15 | −170.30 (11) |
C8—N1—C7—C1 | 176.82 (14) | O2—C14—C15—C16 | 68.48 (16) |
C2—C1—C7—O1 | −163.00 (17) | N2—C14—C15—C16 | −109.73 (13) |
C6—C1—C7—O1 | 19.0 (2) | N4—N3—C16—C17 | −0.49 (15) |
C2—C1—C7—N1 | 19.0 (2) | N4—N3—C16—C15 | −179.14 (11) |
C6—C1—C7—N1 | −159.01 (14) | C14—C15—C16—N3 | 111.39 (14) |
C7—N1—C8—C9 | 32.0 (2) | C14—C15—C16—C17 | −66.96 (18) |
C7—N1—C8—C13 | −149.26 (15) | N3—C16—C17—C18 | 0.00 (16) |
C13—C8—C9—C10 | 1.3 (3) | C15—C16—C17—C18 | 178.46 (13) |
N1—C8—C9—C10 | −179.91 (15) | N3—N4—C18—C17 | −0.86 (16) |
C8—C9—C10—C11 | 0.1 (3) | N3—N4—C18—C19 | 178.99 (13) |
C9—C10—C11—C12 | −1.0 (3) | C16—C17—C18—N4 | 0.50 (16) |
C10—C11—C12—C13 | 0.4 (2) | C16—C17—C18—C19 | −179.31 (16) |
Cg1 and Cg3 are the centroids of the N3,N4,C16–C18 and C8–C13 rings respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.88 (2) | 2.09 (2) | 2.7902 (17) | 135.0 (19) |
N2—H2A···N3i | 0.95 (2) | 1.98 (2) | 2.9209 (17) | 176.4 (17) |
N4—H4A···O3ii | 0.92 (2) | 1.88 (2) | 2.7883 (16) | 166.9 (19) |
C12—H12···O3iii | 0.978 (19) | 2.464 (19) | 3.4042 (19) | 161.2 (14) |
O3—H3A···O1 | 0.87 (3) | 1.89 (3) | 2.7445 (16) | 167 (2) |
O3—H3B···O2iv | 0.94 (3) | 1.83 (3) | 2.7575 (15) | 169 (2) |
C15—H15A···Cg3v | 0.957 (19) | 2.893 (18) | 3.8485 (15) | 174.0 (14) |
C19—H19A···Cg1vi | 0.98 (3) | 2.86 (3) | 3.645 (2) | 138 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, y, z+1; (iv) −x+2, −y+1, −z+1; (v) −x+2, −y+1, −z+2; (vi) −x+1, −y+2, −z+2. |
Acknowledgements
The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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