organic compounds
3-[2-(9H-Carbazol-9-yl)ethyl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione dimethyl sulfoxide monosolvate
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, eDepartment of Chemistry, Faculty of Science, Assiut University, 71515 Assiut, Egypt, and fKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C22H18N4S·C2H6OS, the central triazolethione ring is inclined to the carbazole ring system by 13.97 (18)° and to the phenyl ring by 66.4 (1)°. The lattice solvent, dimethyl sulfoxide, is strongly hydrogen bonded to the triazolethione ring. In the crystal, the main molecules form columns parallel to the a axis, with the solvent molecules located between the columns. C—H⋯S hydrogen bonds and C—H⋯π(ring) interactions link adjacent columns. The crystal studied was refined as a two-component twin, with a fractional contribution to the minor domain of 0.0742 (14).
Keywords: crystal structure; carbazole; triazole; π-stacking.
CCDC reference: 1517511
Structure description
Carbazole-containing compounds exhibit various biological activities including cytotoxic, antitumor, antiviral, antimicrobial, antiparasitics, antiserotonin and anti-inflammatory activities (Kumara et al., 2009; Broadbent et al., 1998; Xia et al., 2008). Moreover, some derivatives have also been found to have industrial uses such as electro-photographic applications, in solar cells, as organic photo-refractive materials, and photo-voltaic devices (Chen et al., 2007; Cheng et al., 2008; Hains & Marks, 2008). As part of our studies in this area, we report herein the synthesis and of the title compound.
The dihedral angle between the N1/C1/C6/C7/C12 and N2/N3/N4/C15/C16 rings is 13.97 (18)° while that between the latter ring and the C17–C22 ring is 66.4 (1)°. The triazolethione substituent forms a strong N3—H3A⋯O1 hydrogen bond with the solvent molecule (Table 1 and Fig. 1). In the crystal, the molecules form columns parallel to the a axis with the solvent molecules located between the columns (Fig. 2). Within the columns, the main molecules are associated through a combination of C18—H18⋯S1 hydrogen bonds and C5—H5⋯Cg1 interactions (Table 1, Fig. 3).
Synthesis and crystallization
A mixture of carbohydrazide (0.5 g, 2 mmol), benzoyl acetonitrile (0.3 g, 2 mmol) and piperidine (3 drops) in absolute ethanol (10 ml) was refluxed for 10 h. The reaction mixture was poured onto water and neutralized with diluted HCl (10%) and left at room temperature for some hours. The solid that formed was collected by filtration, washed with water, dried and crystallized from dioxane–H2O (1:1) to afford crystals of good quality for X-ray diffraction. M.p. 505–507 K.
Refinement
Crystal data, data collection and structure . The crystal studied was refined as a two-component twin with a fractional contribution to the minor domain of 0.0742 (14).
details are summarized in Table 2
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Structural data
CCDC reference: 1517511
https://doi.org/10.1107/S2414314616018356/sj4068sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018356/sj4068Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616018356/sj4068Isup3.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).C22H18N4S·C2H6OS | Dx = 1.296 Mg m−3 |
Mr = 448.59 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 9972 reflections |
a = 5.8948 (1) Å | θ = 3.2–72.2° |
b = 17.7215 (4) Å | µ = 2.28 mm−1 |
c = 22.0042 (5) Å | T = 150 K |
V = 2298.66 (8) Å3 | Column, colourless |
Z = 4 | 0.24 × 0.12 × 0.08 mm |
F(000) = 944 |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 34498 measured reflections |
Radiation source: INCOATEC IµS micro-focus source | 34498 independent reflections |
Mirror monochromator | 24539 reflections with I > 2σ(I) |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.2°, θmin = 3.2° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009) | k = −21→21 |
Tmin = 0.62, Tmax = 0.83 | l = −27→26 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0241P)2 + 0.2059P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.116 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.38 e Å−3 |
34498 reflections | Δρmin = −0.25 e Å−3 |
356 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0030 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack x determined using 1668 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.032 (6) |
Experimental. Analysis of 539 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the orthorhombic system and to be twinned by a 173° rotation about the c* axis. The raw data were processed using the multi- component version ofSAINT under control of the two-component orientation file generated by CELL_NOW. |
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. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
S1 | 1.06943 (17) | 0.78038 (6) | 0.62361 (5) | 0.0315 (3) | |
N1 | 0.3120 (6) | 0.67855 (18) | 0.87011 (15) | 0.0282 (7) | |
N2 | 0.6348 (6) | 0.63171 (19) | 0.68193 (16) | 0.0329 (8) | |
N3 | 0.8155 (6) | 0.6571 (2) | 0.64749 (16) | 0.0320 (8) | |
H3A | 0.884 (10) | 0.624 (3) | 0.619 (2) | 0.052 (15)* | |
N4 | 0.7122 (6) | 0.75119 (18) | 0.70175 (15) | 0.0253 (7) | |
C1 | 0.1993 (7) | 0.7399 (2) | 0.89504 (17) | 0.0258 (8) | |
C2 | 0.2655 (8) | 0.8151 (2) | 0.8975 (2) | 0.0322 (9) | |
H2 | 0.405 (9) | 0.833 (3) | 0.879 (2) | 0.040 (13)* | |
C3 | 0.1213 (9) | 0.8654 (2) | 0.9270 (2) | 0.0367 (10) | |
H3 | 0.168 (9) | 0.920 (3) | 0.927 (2) | 0.042 (13)* | |
C4 | −0.0830 (8) | 0.8415 (3) | 0.9527 (2) | 0.0361 (10) | |
H4 | −0.169 (9) | 0.877 (3) | 0.972 (2) | 0.041 (14)* | |
C5 | −0.1487 (7) | 0.7666 (2) | 0.95002 (18) | 0.0310 (9) | |
H5 | −0.293 (8) | 0.751 (2) | 0.968 (2) | 0.031 (12)* | |
C6 | −0.0069 (6) | 0.7149 (2) | 0.92125 (17) | 0.0255 (8) | |
C7 | −0.0203 (7) | 0.6344 (2) | 0.91025 (18) | 0.0270 (8) | |
C8 | −0.1812 (8) | 0.5788 (2) | 0.92297 (19) | 0.0323 (9) | |
H8 | −0.311 (9) | 0.591 (3) | 0.947 (2) | 0.038 (13)* | |
C9 | −0.1437 (9) | 0.5066 (3) | 0.9021 (2) | 0.0390 (11) | |
H9 | −0.248 (10) | 0.473 (3) | 0.909 (2) | 0.046 (15)* | |
C10 | 0.0520 (9) | 0.4881 (2) | 0.8697 (2) | 0.0401 (11) | |
H10 | 0.073 (9) | 0.435 (3) | 0.855 (2) | 0.046 (14)* | |
C11 | 0.2156 (8) | 0.5416 (2) | 0.8574 (2) | 0.0347 (10) | |
H11 | 0.359 (9) | 0.531 (3) | 0.833 (2) | 0.036 (13)* | |
C12 | 0.1769 (7) | 0.6148 (2) | 0.87782 (18) | 0.0268 (8) | |
C13 | 0.4908 (7) | 0.6834 (3) | 0.82506 (19) | 0.0302 (9) | |
H13B | 0.584 (9) | 0.639 (3) | 0.829 (2) | 0.032 (12)* | |
H13A | 0.595 (9) | 0.726 (3) | 0.834 (2) | 0.041 (13)* | |
C14 | 0.3934 (7) | 0.6885 (2) | 0.76079 (18) | 0.0286 (8) | |
H14B | 0.299 (8) | 0.645 (3) | 0.754 (2) | 0.029 (11)* | |
H14A | 0.290 (9) | 0.732 (3) | 0.756 (2) | 0.048 (14)* | |
C15 | 0.5752 (7) | 0.6896 (2) | 0.71422 (17) | 0.0272 (8) | |
C16 | 0.8664 (7) | 0.7295 (2) | 0.65795 (17) | 0.0261 (8) | |
C17 | 0.6927 (7) | 0.8246 (2) | 0.73026 (18) | 0.0255 (8) | |
C18 | 0.4986 (7) | 0.8669 (2) | 0.7204 (2) | 0.0324 (9) | |
H18 | 0.380 (11) | 0.848 (3) | 0.693 (3) | 0.057 (16)* | |
C19 | 0.4713 (8) | 0.9348 (3) | 0.7511 (2) | 0.0371 (10) | |
H19 | 0.332 (9) | 0.963 (3) | 0.746 (2) | 0.039 (13)* | |
C20 | 0.6393 (9) | 0.9604 (2) | 0.7903 (2) | 0.0374 (11) | |
H20 | 0.616 (9) | 1.009 (3) | 0.812 (2) | 0.040 (13)* | |
C21 | 0.8346 (9) | 0.9183 (2) | 0.7986 (2) | 0.0364 (10) | |
H21 | 0.951 (9) | 0.935 (3) | 0.827 (2) | 0.041 (13)* | |
C22 | 0.8610 (7) | 0.8494 (2) | 0.76912 (19) | 0.0310 (9) | |
H22 | 0.992 (8) | 0.816 (3) | 0.777 (2) | 0.035 (12)* | |
S2 | 1.1260 (2) | 0.56418 (7) | 0.51143 (5) | 0.0425 (3) | |
O1 | 0.9739 (6) | 0.55716 (18) | 0.56576 (16) | 0.0481 (9) | |
C23 | 1.0596 (11) | 0.6521 (3) | 0.4773 (2) | 0.0563 (14) | |
H23A | 1.0668 | 0.6921 | 0.5080 | 0.084* | |
H23B | 0.9064 | 0.6500 | 0.4601 | 0.084* | |
H23C | 1.1690 | 0.6628 | 0.4449 | 0.084* | |
C24 | 1.3961 (11) | 0.5911 (5) | 0.5403 (3) | 0.090 (3) | |
H24A | 1.4647 | 0.5483 | 0.5617 | 0.135* | |
H24B | 1.3778 | 0.6334 | 0.5686 | 0.135* | |
H24C | 1.4945 | 0.6064 | 0.5066 | 0.135* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0302 (5) | 0.0329 (5) | 0.0313 (5) | −0.0069 (4) | 0.0071 (4) | −0.0011 (4) |
N1 | 0.0288 (16) | 0.0304 (17) | 0.0254 (17) | −0.0004 (13) | 0.0068 (14) | −0.0012 (14) |
N2 | 0.037 (2) | 0.0333 (18) | 0.0282 (18) | −0.0090 (15) | 0.0100 (16) | −0.0019 (15) |
N3 | 0.0364 (19) | 0.0307 (17) | 0.0290 (18) | −0.0084 (15) | 0.0110 (16) | −0.0029 (15) |
N4 | 0.0255 (16) | 0.0271 (16) | 0.0233 (16) | −0.0031 (13) | 0.0029 (14) | −0.0007 (14) |
C1 | 0.028 (2) | 0.029 (2) | 0.0200 (19) | 0.0004 (15) | −0.0004 (15) | 0.0004 (15) |
C2 | 0.034 (2) | 0.034 (2) | 0.028 (2) | −0.0039 (17) | −0.0037 (18) | 0.0038 (18) |
C3 | 0.050 (3) | 0.028 (2) | 0.032 (2) | −0.0004 (19) | −0.009 (2) | 0.0000 (18) |
C4 | 0.041 (2) | 0.037 (2) | 0.030 (2) | 0.010 (2) | −0.004 (2) | −0.0064 (18) |
C5 | 0.030 (2) | 0.039 (2) | 0.0234 (19) | 0.0045 (17) | −0.0013 (17) | −0.0029 (17) |
C6 | 0.0266 (19) | 0.032 (2) | 0.0177 (17) | −0.0004 (16) | −0.0009 (15) | −0.0004 (16) |
C7 | 0.030 (2) | 0.033 (2) | 0.0185 (18) | −0.0012 (16) | −0.0004 (16) | −0.0002 (16) |
C8 | 0.032 (2) | 0.040 (2) | 0.025 (2) | −0.0063 (18) | 0.0018 (18) | 0.0035 (18) |
C9 | 0.049 (3) | 0.034 (2) | 0.034 (2) | −0.012 (2) | 0.000 (2) | 0.005 (2) |
C10 | 0.057 (3) | 0.029 (2) | 0.034 (2) | 0.000 (2) | 0.001 (2) | −0.0023 (19) |
C11 | 0.044 (3) | 0.032 (2) | 0.028 (2) | 0.0043 (18) | 0.006 (2) | −0.0008 (17) |
C12 | 0.031 (2) | 0.0289 (18) | 0.0200 (18) | −0.0012 (15) | 0.0010 (18) | 0.0006 (16) |
C13 | 0.025 (2) | 0.041 (2) | 0.025 (2) | 0.0001 (18) | 0.0054 (16) | 0.0025 (19) |
C14 | 0.026 (2) | 0.0333 (19) | 0.026 (2) | −0.0033 (17) | 0.0032 (17) | 0.0012 (17) |
C15 | 0.028 (2) | 0.0293 (18) | 0.0242 (19) | −0.0049 (16) | 0.0006 (17) | 0.0026 (16) |
C16 | 0.0274 (19) | 0.0290 (19) | 0.0220 (18) | −0.0018 (15) | 0.0017 (16) | −0.0010 (16) |
C17 | 0.0264 (19) | 0.0267 (19) | 0.0233 (19) | −0.0005 (15) | 0.0021 (16) | 0.0002 (16) |
C18 | 0.027 (2) | 0.034 (2) | 0.036 (2) | −0.0009 (16) | −0.0023 (18) | 0.0041 (19) |
C19 | 0.033 (2) | 0.032 (2) | 0.046 (3) | 0.0081 (18) | 0.009 (2) | 0.007 (2) |
C20 | 0.053 (3) | 0.028 (2) | 0.032 (2) | 0.0033 (19) | 0.009 (2) | 0.0000 (18) |
C21 | 0.047 (3) | 0.033 (2) | 0.030 (2) | −0.0006 (19) | −0.005 (2) | −0.0022 (19) |
C22 | 0.033 (2) | 0.031 (2) | 0.029 (2) | 0.0021 (17) | −0.0037 (18) | −0.0009 (17) |
S2 | 0.0393 (6) | 0.0542 (7) | 0.0341 (6) | 0.0016 (5) | 0.0064 (5) | −0.0116 (5) |
O1 | 0.060 (2) | 0.0364 (17) | 0.047 (2) | −0.0046 (15) | 0.0236 (17) | −0.0083 (16) |
C23 | 0.066 (4) | 0.062 (3) | 0.041 (3) | −0.014 (3) | −0.001 (3) | 0.001 (3) |
C24 | 0.038 (3) | 0.171 (8) | 0.061 (4) | 0.006 (4) | −0.005 (3) | −0.028 (5) |
S1—C16 | 1.678 (4) | C10—H10 | 1.00 (5) |
N1—C1 | 1.387 (5) | C11—C12 | 1.391 (6) |
N1—C12 | 1.393 (5) | C11—H11 | 1.02 (5) |
N1—C13 | 1.449 (5) | C13—C14 | 1.529 (6) |
N2—C15 | 1.297 (5) | C13—H13B | 0.96 (5) |
N2—N3 | 1.383 (5) | C13—H13A | 1.00 (5) |
N3—C16 | 1.338 (5) | C14—C15 | 1.483 (5) |
N3—H3A | 0.95 (6) | C14—H14B | 0.97 (5) |
N4—C16 | 1.380 (5) | C14—H14A | 0.99 (5) |
N4—C15 | 1.385 (5) | C17—C22 | 1.382 (6) |
N4—C17 | 1.448 (5) | C17—C18 | 1.385 (6) |
C1—C2 | 1.391 (6) | C18—C19 | 1.389 (7) |
C1—C6 | 1.416 (6) | C18—H18 | 0.98 (6) |
C2—C3 | 1.392 (6) | C19—C20 | 1.389 (7) |
C2—H2 | 0.97 (5) | C19—H19 | 0.97 (5) |
C3—C4 | 1.397 (7) | C20—C21 | 1.384 (7) |
C3—H3 | 1.00 (5) | C20—H20 | 1.00 (5) |
C4—C5 | 1.383 (6) | C21—C22 | 1.390 (6) |
C4—H4 | 0.91 (5) | C21—H21 | 0.97 (5) |
C5—C6 | 1.392 (6) | C22—H22 | 0.98 (5) |
C5—H5 | 0.99 (5) | S2—O1 | 1.500 (3) |
C6—C7 | 1.449 (6) | S2—C23 | 1.773 (6) |
C7—C8 | 1.396 (6) | S2—C24 | 1.779 (7) |
C7—C12 | 1.408 (6) | C23—H23A | 0.9800 |
C8—C9 | 1.377 (7) | C23—H23B | 0.9800 |
C8—H8 | 0.96 (5) | C23—H23C | 0.9800 |
C9—C10 | 1.395 (7) | C24—H24A | 0.9800 |
C9—H9 | 0.87 (6) | C24—H24B | 0.9800 |
C10—C11 | 1.379 (7) | C24—H24C | 0.9800 |
C1—N1—C12 | 108.3 (3) | N1—C13—H13A | 111 (3) |
C1—N1—C13 | 124.9 (3) | C14—C13—H13A | 111 (3) |
C12—N1—C13 | 123.2 (3) | H13B—C13—H13A | 105 (4) |
C15—N2—N3 | 104.6 (3) | C15—C14—C13 | 111.6 (3) |
C16—N3—N2 | 113.0 (3) | C15—C14—H14B | 109 (3) |
C16—N3—H3A | 128 (3) | C13—C14—H14B | 108 (3) |
N2—N3—H3A | 119 (3) | C15—C14—H14A | 112 (3) |
C16—N4—C15 | 107.6 (3) | C13—C14—H14A | 112 (3) |
C16—N4—C17 | 127.2 (3) | H14B—C14—H14A | 105 (4) |
C15—N4—C17 | 125.1 (3) | N2—C15—N4 | 110.9 (3) |
N1—C1—C2 | 129.2 (4) | N2—C15—C14 | 124.3 (4) |
N1—C1—C6 | 109.2 (3) | N4—C15—C14 | 124.6 (4) |
C2—C1—C6 | 121.6 (4) | N3—C16—N4 | 103.9 (3) |
C1—C2—C3 | 117.4 (4) | N3—C16—S1 | 126.7 (3) |
C1—C2—H2 | 123 (3) | N4—C16—S1 | 129.4 (3) |
C3—C2—H2 | 120 (3) | C22—C17—C18 | 121.2 (4) |
C2—C3—C4 | 121.4 (4) | C22—C17—N4 | 119.8 (4) |
C2—C3—H3 | 117 (3) | C18—C17—N4 | 118.9 (4) |
C4—C3—H3 | 122 (3) | C17—C18—C19 | 119.2 (4) |
C5—C4—C3 | 121.1 (4) | C17—C18—H18 | 120 (3) |
C5—C4—H4 | 121 (3) | C19—C18—H18 | 121 (3) |
C3—C4—H4 | 117 (3) | C18—C19—C20 | 120.2 (4) |
C4—C5—C6 | 118.8 (4) | C18—C19—H19 | 119 (3) |
C4—C5—H5 | 120 (3) | C20—C19—H19 | 121 (3) |
C6—C5—H5 | 121 (3) | C21—C20—C19 | 120.0 (4) |
C5—C6—C1 | 119.7 (4) | C21—C20—H20 | 121 (3) |
C5—C6—C7 | 133.7 (4) | C19—C20—H20 | 119 (3) |
C1—C6—C7 | 106.6 (3) | C20—C21—C22 | 120.3 (4) |
C8—C7—C12 | 119.2 (4) | C20—C21—H21 | 120 (3) |
C8—C7—C6 | 134.3 (4) | C22—C21—H21 | 119 (3) |
C12—C7—C6 | 106.5 (3) | C17—C22—C21 | 119.2 (4) |
C9—C8—C7 | 118.7 (4) | C17—C22—H22 | 119 (3) |
C9—C8—H8 | 121 (3) | C21—C22—H22 | 122 (3) |
C7—C8—H8 | 120 (3) | O1—S2—C23 | 106.2 (2) |
C8—C9—C10 | 121.4 (4) | O1—S2—C24 | 105.8 (3) |
C8—C9—H9 | 118 (4) | C23—S2—C24 | 96.5 (4) |
C10—C9—H9 | 121 (4) | S2—C23—H23A | 109.5 |
C11—C10—C9 | 121.2 (4) | S2—C23—H23B | 109.5 |
C11—C10—H10 | 120 (3) | H23A—C23—H23B | 109.5 |
C9—C10—H10 | 119 (3) | S2—C23—H23C | 109.5 |
C10—C11—C12 | 117.6 (4) | H23A—C23—H23C | 109.5 |
C10—C11—H11 | 124 (3) | H23B—C23—H23C | 109.5 |
C12—C11—H11 | 119 (3) | S2—C24—H24A | 109.5 |
C11—C12—N1 | 128.6 (4) | S2—C24—H24B | 109.5 |
C11—C12—C7 | 122.0 (4) | H24A—C24—H24B | 109.5 |
N1—C12—C7 | 109.4 (3) | S2—C24—H24C | 109.5 |
N1—C13—C14 | 111.3 (3) | H24A—C24—H24C | 109.5 |
N1—C13—H13B | 107 (3) | H24B—C24—H24C | 109.5 |
C14—C13—H13B | 111 (3) | ||
C15—N2—N3—C16 | −0.3 (5) | C6—C7—C12—C11 | −177.4 (4) |
C12—N1—C1—C2 | −179.0 (4) | C8—C7—C12—N1 | 179.7 (4) |
C13—N1—C1—C2 | −20.1 (7) | C6—C7—C12—N1 | 1.7 (4) |
C12—N1—C1—C6 | 2.3 (4) | C1—N1—C13—C14 | −84.9 (5) |
C13—N1—C1—C6 | 161.2 (4) | C12—N1—C13—C14 | 71.1 (5) |
N1—C1—C2—C3 | −178.3 (4) | N1—C13—C14—C15 | −177.1 (3) |
C6—C1—C2—C3 | 0.3 (6) | N3—N2—C15—N4 | −0.2 (5) |
C1—C2—C3—C4 | −0.6 (7) | N3—N2—C15—C14 | −176.9 (4) |
C2—C3—C4—C5 | 0.4 (7) | C16—N4—C15—N2 | 0.6 (5) |
C3—C4—C5—C6 | 0.1 (6) | C17—N4—C15—N2 | −179.5 (4) |
C4—C5—C6—C1 | −0.5 (6) | C16—N4—C15—C14 | 177.3 (4) |
C4—C5—C6—C7 | 179.9 (4) | C17—N4—C15—C14 | −2.8 (6) |
N1—C1—C6—C5 | 179.1 (3) | C13—C14—C15—N2 | 101.3 (5) |
C2—C1—C6—C5 | 0.3 (6) | C13—C14—C15—N4 | −74.9 (5) |
N1—C1—C6—C7 | −1.2 (4) | N2—N3—C16—N4 | 0.7 (5) |
C2—C1—C6—C7 | 180.0 (4) | N2—N3—C16—S1 | −178.3 (3) |
C5—C6—C7—C8 | 1.8 (8) | C15—N4—C16—N3 | −0.8 (4) |
C1—C6—C7—C8 | −177.9 (4) | C17—N4—C16—N3 | 179.3 (4) |
C5—C6—C7—C12 | 179.4 (4) | C15—N4—C16—S1 | 178.2 (3) |
C1—C6—C7—C12 | −0.3 (4) | C17—N4—C16—S1 | −1.7 (6) |
C12—C7—C8—C9 | −1.4 (6) | C16—N4—C17—C22 | −68.5 (5) |
C6—C7—C8—C9 | 175.9 (4) | C15—N4—C17—C22 | 111.6 (5) |
C7—C8—C9—C10 | 1.1 (7) | C16—N4—C17—C18 | 114.9 (5) |
C8—C9—C10—C11 | 0.0 (7) | C15—N4—C17—C18 | −65.0 (5) |
C9—C10—C11—C12 | −0.7 (7) | C22—C17—C18—C19 | −1.3 (6) |
C10—C11—C12—N1 | −178.5 (4) | N4—C17—C18—C19 | 175.3 (4) |
C10—C11—C12—C7 | 0.4 (6) | C17—C18—C19—C20 | 1.2 (7) |
C1—N1—C12—C11 | 176.5 (4) | C18—C19—C20—C21 | 0.2 (7) |
C13—N1—C12—C11 | 17.1 (7) | C19—C20—C21—C22 | −1.7 (7) |
C1—N1—C12—C7 | −2.5 (4) | C18—C17—C22—C21 | −0.2 (6) |
C13—N1—C12—C7 | −161.9 (4) | N4—C17—C22—C21 | −176.7 (4) |
C8—C7—C12—C11 | 0.7 (6) | C20—C21—C22—C17 | 1.6 (7) |
Cg1 is the centroid of the C1–C6 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1 | 0.95 (5) | 1.75 (5) | 2.691 (5) | 172 (6) |
C3—H3···O1i | 1.01 (5) | 2.58 (5) | 3.448 (5) | 145 (4) |
C18—H18···S1ii | 0.98 (6) | 2.67 (6) | 3.645 (4) | 173 (4) |
C5—H5···Cg1iii | 0.98 (5) | 2.64 (4) | 3.422 (4) | 137 (3) |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −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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