organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

3-[2-(9H-Carbazol-9-yl)eth­yl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione di­methyl sulfoxide mono­solvate

CROSSMARK_Color_square_no_text.svg

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

Edited by J. Simpson, University of Otago, New Zealand (Received 10 November 2016; accepted 16 November 2016; online 22 November 2016)

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).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Carbazole-containing compounds exhibit various biological activities including cytotoxic, anti­tumor, anti­viral, anti­microbial, anti­parasitics, anti­serotonin and anti-inflammatory activities (Kumara et al., 2009[Kumara Swamy, K. C., Bhuvan Kumar, N. N., Balaraman, E. & Pavan Kumar, K. V. P. (2009). Chem. Rev. 109, 2551-2651.]; Broadbent et al., 1998[Broadbent, A., Thomas, H. & Broadbent, S. (1998). Curr. Med. Chem. 5, 469-491.]; Xia et al., 2008[Xia, Y., Fan, C.-D., Zhao, B.-X., Zhao, J., Shin, D.-S. & Miao, J.-Y. (2008). Eur. J. Med. Chem. 43, 2347-2353.]). 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[Chen, R., Yang, X., Tian, H. & Sun, L. (2007). J. Photochem. Photobiol. Chem. 189, 295-300.]; Cheng et al., 2008[Cheng, T., Lin, T., Brady, R. & Wang, X. (2008). Fibers Polym. 9, 521-526.]; Hains & Marks, 2008[Hains, W. & Marks, T. J. (2008). Appl. Phys. Lett. 92, 023504.]). As part of our studies in this area, we report herein the synthesis and crystal structure 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[link] and Fig. 1[link]). In the crystal, the mol­ecules form columns parallel to the a axis with the solvent mol­ecules located between the columns (Fig. 2[link]). Within the columns, the main mol­ecules are associated through a combination of C18—H18⋯S1 hydrogen bonds and C5—H5⋯Cg1 inter­actions (Table 1[link], Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A D—H H⋯A DA 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+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x-1, y, z; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].
[Figure 1]
Figure 1
The title mol­ecule, showing the atom-labeling scheme and 50% probability ellipsoids. The N—H⋯O hydrogen bond is shown as a dotted line.
[Figure 2]
Figure 2
The packing of the title mol­ecule, viewed along the a axis. N—H⋯O and C—H⋯S hydrogen bonds are shown, respectively, as blue and black dotted lines.
[Figure 3]
Figure 3
Detail of the inter­molecular inter­actions. N—H⋯O and C—H⋯S hydrogen bonds are shown, respectively, as blue and black dotted lines while the C—H⋯π(ring) inter­action is shown as an orange dotted line.

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 refinement details are summarized in Table 2[link]. The crystal studied was refined as a two-component twin with a fractional contribution to the minor domain of 0.0742 (14).

Table 2
Experimental details

Crystal data
Chemical formula C22H18N4S·C2H6OS
Mr 448.59
Crystal system, space group Orthorhombic, P212121
Temperature (K) 150
a, b, c (Å) 5.8948 (1), 17.7215 (4), 22.0042 (5)
V3) 2298.66 (8)
Z 4
Radiation type Cu Kα
μ (mm−1) 2.28
Crystal size (mm) 0.24 × 0.12 × 0.08
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan (TWINABS; Sheldrick, 2009[Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Germany.])
Tmin, Tmax 0.62, 0.83
No. of measured, independent and observed [I > 2σ(I)] reflections 34498, 34498, 24539
(sin θ/λ)max−1) 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.116, 1.03
No. of reflections 34498
No. of parameters 356
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.38, −0.25
Absolute structure Flack x determined using 1668 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.032 (6)
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: 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).

3-[2-(9H-Carbazol-9-yl)ethyl]-4-phenyl-1H-1,2,4-triazole-5(4H)-thione dimethyl sulfoxide monosolvate top
Crystal data top
C22H18N4S·C2H6OSDx = 1.296 Mg m3
Mr = 448.59Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 9972 reflections
a = 5.8948 (1) Åθ = 3.2–72.2°
b = 17.7215 (4) ŵ = 2.28 mm1
c = 22.0042 (5) ÅT = 150 K
V = 2298.66 (8) Å3Column, colourless
Z = 40.24 × 0.12 × 0.08 mm
F(000) = 944
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
34498 measured reflections
Radiation source: INCOATEC IµS micro-focus source34498 independent reflections
Mirror monochromator24539 reflections with I > 2σ(I)
Detector resolution: 10.4167 pixels mm-1θmax = 72.2°, θmin = 3.2°
ω scansh = 77
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2009)
k = 2121
Tmin = 0.62, Tmax = 0.83l = 2726
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.03Δρmax = 0.38 e Å3
34498 reflectionsΔρmin = 0.25 e Å3
356 parametersExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0030 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack x determined using 1668 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.032 (6)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S11.06943 (17)0.78038 (6)0.62361 (5)0.0315 (3)
N10.3120 (6)0.67855 (18)0.87011 (15)0.0282 (7)
N20.6348 (6)0.63171 (19)0.68193 (16)0.0329 (8)
N30.8155 (6)0.6571 (2)0.64749 (16)0.0320 (8)
H3A0.884 (10)0.624 (3)0.619 (2)0.052 (15)*
N40.7122 (6)0.75119 (18)0.70175 (15)0.0253 (7)
C10.1993 (7)0.7399 (2)0.89504 (17)0.0258 (8)
C20.2655 (8)0.8151 (2)0.8975 (2)0.0322 (9)
H20.405 (9)0.833 (3)0.879 (2)0.040 (13)*
C30.1213 (9)0.8654 (2)0.9270 (2)0.0367 (10)
H30.168 (9)0.920 (3)0.927 (2)0.042 (13)*
C40.0830 (8)0.8415 (3)0.9527 (2)0.0361 (10)
H40.169 (9)0.877 (3)0.972 (2)0.041 (14)*
C50.1487 (7)0.7666 (2)0.95002 (18)0.0310 (9)
H50.293 (8)0.751 (2)0.968 (2)0.031 (12)*
C60.0069 (6)0.7149 (2)0.92125 (17)0.0255 (8)
C70.0203 (7)0.6344 (2)0.91025 (18)0.0270 (8)
C80.1812 (8)0.5788 (2)0.92297 (19)0.0323 (9)
H80.311 (9)0.591 (3)0.947 (2)0.038 (13)*
C90.1437 (9)0.5066 (3)0.9021 (2)0.0390 (11)
H90.248 (10)0.473 (3)0.909 (2)0.046 (15)*
C100.0520 (9)0.4881 (2)0.8697 (2)0.0401 (11)
H100.073 (9)0.435 (3)0.855 (2)0.046 (14)*
C110.2156 (8)0.5416 (2)0.8574 (2)0.0347 (10)
H110.359 (9)0.531 (3)0.833 (2)0.036 (13)*
C120.1769 (7)0.6148 (2)0.87782 (18)0.0268 (8)
C130.4908 (7)0.6834 (3)0.82506 (19)0.0302 (9)
H13B0.584 (9)0.639 (3)0.829 (2)0.032 (12)*
H13A0.595 (9)0.726 (3)0.834 (2)0.041 (13)*
C140.3934 (7)0.6885 (2)0.76079 (18)0.0286 (8)
H14B0.299 (8)0.645 (3)0.754 (2)0.029 (11)*
H14A0.290 (9)0.732 (3)0.756 (2)0.048 (14)*
C150.5752 (7)0.6896 (2)0.71422 (17)0.0272 (8)
C160.8664 (7)0.7295 (2)0.65795 (17)0.0261 (8)
C170.6927 (7)0.8246 (2)0.73026 (18)0.0255 (8)
C180.4986 (7)0.8669 (2)0.7204 (2)0.0324 (9)
H180.380 (11)0.848 (3)0.693 (3)0.057 (16)*
C190.4713 (8)0.9348 (3)0.7511 (2)0.0371 (10)
H190.332 (9)0.963 (3)0.746 (2)0.039 (13)*
C200.6393 (9)0.9604 (2)0.7903 (2)0.0374 (11)
H200.616 (9)1.009 (3)0.812 (2)0.040 (13)*
C210.8346 (9)0.9183 (2)0.7986 (2)0.0364 (10)
H210.951 (9)0.935 (3)0.827 (2)0.041 (13)*
C220.8610 (7)0.8494 (2)0.76912 (19)0.0310 (9)
H220.992 (8)0.816 (3)0.777 (2)0.035 (12)*
S21.1260 (2)0.56418 (7)0.51143 (5)0.0425 (3)
O10.9739 (6)0.55716 (18)0.56576 (16)0.0481 (9)
C231.0596 (11)0.6521 (3)0.4773 (2)0.0563 (14)
H23A1.06680.69210.50800.084*
H23B0.90640.65000.46010.084*
H23C1.16900.66280.44490.084*
C241.3961 (11)0.5911 (5)0.5403 (3)0.090 (3)
H24A1.46470.54830.56170.135*
H24B1.37780.63340.56860.135*
H24C1.49450.60640.50660.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0302 (5)0.0329 (5)0.0313 (5)0.0069 (4)0.0071 (4)0.0011 (4)
N10.0288 (16)0.0304 (17)0.0254 (17)0.0004 (13)0.0068 (14)0.0012 (14)
N20.037 (2)0.0333 (18)0.0282 (18)0.0090 (15)0.0100 (16)0.0019 (15)
N30.0364 (19)0.0307 (17)0.0290 (18)0.0084 (15)0.0110 (16)0.0029 (15)
N40.0255 (16)0.0271 (16)0.0233 (16)0.0031 (13)0.0029 (14)0.0007 (14)
C10.028 (2)0.029 (2)0.0200 (19)0.0004 (15)0.0004 (15)0.0004 (15)
C20.034 (2)0.034 (2)0.028 (2)0.0039 (17)0.0037 (18)0.0038 (18)
C30.050 (3)0.028 (2)0.032 (2)0.0004 (19)0.009 (2)0.0000 (18)
C40.041 (2)0.037 (2)0.030 (2)0.010 (2)0.004 (2)0.0064 (18)
C50.030 (2)0.039 (2)0.0234 (19)0.0045 (17)0.0013 (17)0.0029 (17)
C60.0266 (19)0.032 (2)0.0177 (17)0.0004 (16)0.0009 (15)0.0004 (16)
C70.030 (2)0.033 (2)0.0185 (18)0.0012 (16)0.0004 (16)0.0002 (16)
C80.032 (2)0.040 (2)0.025 (2)0.0063 (18)0.0018 (18)0.0035 (18)
C90.049 (3)0.034 (2)0.034 (2)0.012 (2)0.000 (2)0.005 (2)
C100.057 (3)0.029 (2)0.034 (2)0.000 (2)0.001 (2)0.0023 (19)
C110.044 (3)0.032 (2)0.028 (2)0.0043 (18)0.006 (2)0.0008 (17)
C120.031 (2)0.0289 (18)0.0200 (18)0.0012 (15)0.0010 (18)0.0006 (16)
C130.025 (2)0.041 (2)0.025 (2)0.0001 (18)0.0054 (16)0.0025 (19)
C140.026 (2)0.0333 (19)0.026 (2)0.0033 (17)0.0032 (17)0.0012 (17)
C150.028 (2)0.0293 (18)0.0242 (19)0.0049 (16)0.0006 (17)0.0026 (16)
C160.0274 (19)0.0290 (19)0.0220 (18)0.0018 (15)0.0017 (16)0.0010 (16)
C170.0264 (19)0.0267 (19)0.0233 (19)0.0005 (15)0.0021 (16)0.0002 (16)
C180.027 (2)0.034 (2)0.036 (2)0.0009 (16)0.0023 (18)0.0041 (19)
C190.033 (2)0.032 (2)0.046 (3)0.0081 (18)0.009 (2)0.007 (2)
C200.053 (3)0.028 (2)0.032 (2)0.0033 (19)0.009 (2)0.0000 (18)
C210.047 (3)0.033 (2)0.030 (2)0.0006 (19)0.005 (2)0.0022 (19)
C220.033 (2)0.031 (2)0.029 (2)0.0021 (17)0.0037 (18)0.0009 (17)
S20.0393 (6)0.0542 (7)0.0341 (6)0.0016 (5)0.0064 (5)0.0116 (5)
O10.060 (2)0.0364 (17)0.047 (2)0.0046 (15)0.0236 (17)0.0083 (16)
C230.066 (4)0.062 (3)0.041 (3)0.014 (3)0.001 (3)0.001 (3)
C240.038 (3)0.171 (8)0.061 (4)0.006 (4)0.005 (3)0.028 (5)
Geometric parameters (Å, º) top
S1—C161.678 (4)C10—H101.00 (5)
N1—C11.387 (5)C11—C121.391 (6)
N1—C121.393 (5)C11—H111.02 (5)
N1—C131.449 (5)C13—C141.529 (6)
N2—C151.297 (5)C13—H13B0.96 (5)
N2—N31.383 (5)C13—H13A1.00 (5)
N3—C161.338 (5)C14—C151.483 (5)
N3—H3A0.95 (6)C14—H14B0.97 (5)
N4—C161.380 (5)C14—H14A0.99 (5)
N4—C151.385 (5)C17—C221.382 (6)
N4—C171.448 (5)C17—C181.385 (6)
C1—C21.391 (6)C18—C191.389 (7)
C1—C61.416 (6)C18—H180.98 (6)
C2—C31.392 (6)C19—C201.389 (7)
C2—H20.97 (5)C19—H190.97 (5)
C3—C41.397 (7)C20—C211.384 (7)
C3—H31.00 (5)C20—H201.00 (5)
C4—C51.383 (6)C21—C221.390 (6)
C4—H40.91 (5)C21—H210.97 (5)
C5—C61.392 (6)C22—H220.98 (5)
C5—H50.99 (5)S2—O11.500 (3)
C6—C71.449 (6)S2—C231.773 (6)
C7—C81.396 (6)S2—C241.779 (7)
C7—C121.408 (6)C23—H23A0.9800
C8—C91.377 (7)C23—H23B0.9800
C8—H80.96 (5)C23—H23C0.9800
C9—C101.395 (7)C24—H24A0.9800
C9—H90.87 (6)C24—H24B0.9800
C10—C111.379 (7)C24—H24C0.9800
C1—N1—C12108.3 (3)N1—C13—H13A111 (3)
C1—N1—C13124.9 (3)C14—C13—H13A111 (3)
C12—N1—C13123.2 (3)H13B—C13—H13A105 (4)
C15—N2—N3104.6 (3)C15—C14—C13111.6 (3)
C16—N3—N2113.0 (3)C15—C14—H14B109 (3)
C16—N3—H3A128 (3)C13—C14—H14B108 (3)
N2—N3—H3A119 (3)C15—C14—H14A112 (3)
C16—N4—C15107.6 (3)C13—C14—H14A112 (3)
C16—N4—C17127.2 (3)H14B—C14—H14A105 (4)
C15—N4—C17125.1 (3)N2—C15—N4110.9 (3)
N1—C1—C2129.2 (4)N2—C15—C14124.3 (4)
N1—C1—C6109.2 (3)N4—C15—C14124.6 (4)
C2—C1—C6121.6 (4)N3—C16—N4103.9 (3)
C1—C2—C3117.4 (4)N3—C16—S1126.7 (3)
C1—C2—H2123 (3)N4—C16—S1129.4 (3)
C3—C2—H2120 (3)C22—C17—C18121.2 (4)
C2—C3—C4121.4 (4)C22—C17—N4119.8 (4)
C2—C3—H3117 (3)C18—C17—N4118.9 (4)
C4—C3—H3122 (3)C17—C18—C19119.2 (4)
C5—C4—C3121.1 (4)C17—C18—H18120 (3)
C5—C4—H4121 (3)C19—C18—H18121 (3)
C3—C4—H4117 (3)C18—C19—C20120.2 (4)
C4—C5—C6118.8 (4)C18—C19—H19119 (3)
C4—C5—H5120 (3)C20—C19—H19121 (3)
C6—C5—H5121 (3)C21—C20—C19120.0 (4)
C5—C6—C1119.7 (4)C21—C20—H20121 (3)
C5—C6—C7133.7 (4)C19—C20—H20119 (3)
C1—C6—C7106.6 (3)C20—C21—C22120.3 (4)
C8—C7—C12119.2 (4)C20—C21—H21120 (3)
C8—C7—C6134.3 (4)C22—C21—H21119 (3)
C12—C7—C6106.5 (3)C17—C22—C21119.2 (4)
C9—C8—C7118.7 (4)C17—C22—H22119 (3)
C9—C8—H8121 (3)C21—C22—H22122 (3)
C7—C8—H8120 (3)O1—S2—C23106.2 (2)
C8—C9—C10121.4 (4)O1—S2—C24105.8 (3)
C8—C9—H9118 (4)C23—S2—C2496.5 (4)
C10—C9—H9121 (4)S2—C23—H23A109.5
C11—C10—C9121.2 (4)S2—C23—H23B109.5
C11—C10—H10120 (3)H23A—C23—H23B109.5
C9—C10—H10119 (3)S2—C23—H23C109.5
C10—C11—C12117.6 (4)H23A—C23—H23C109.5
C10—C11—H11124 (3)H23B—C23—H23C109.5
C12—C11—H11119 (3)S2—C24—H24A109.5
C11—C12—N1128.6 (4)S2—C24—H24B109.5
C11—C12—C7122.0 (4)H24A—C24—H24B109.5
N1—C12—C7109.4 (3)S2—C24—H24C109.5
N1—C13—C14111.3 (3)H24A—C24—H24C109.5
N1—C13—H13B107 (3)H24B—C24—H24C109.5
C14—C13—H13B111 (3)
C15—N2—N3—C160.3 (5)C6—C7—C12—C11177.4 (4)
C12—N1—C1—C2179.0 (4)C8—C7—C12—N1179.7 (4)
C13—N1—C1—C220.1 (7)C6—C7—C12—N11.7 (4)
C12—N1—C1—C62.3 (4)C1—N1—C13—C1484.9 (5)
C13—N1—C1—C6161.2 (4)C12—N1—C13—C1471.1 (5)
N1—C1—C2—C3178.3 (4)N1—C13—C14—C15177.1 (3)
C6—C1—C2—C30.3 (6)N3—N2—C15—N40.2 (5)
C1—C2—C3—C40.6 (7)N3—N2—C15—C14176.9 (4)
C2—C3—C4—C50.4 (7)C16—N4—C15—N20.6 (5)
C3—C4—C5—C60.1 (6)C17—N4—C15—N2179.5 (4)
C4—C5—C6—C10.5 (6)C16—N4—C15—C14177.3 (4)
C4—C5—C6—C7179.9 (4)C17—N4—C15—C142.8 (6)
N1—C1—C6—C5179.1 (3)C13—C14—C15—N2101.3 (5)
C2—C1—C6—C50.3 (6)C13—C14—C15—N474.9 (5)
N1—C1—C6—C71.2 (4)N2—N3—C16—N40.7 (5)
C2—C1—C6—C7180.0 (4)N2—N3—C16—S1178.3 (3)
C5—C6—C7—C81.8 (8)C15—N4—C16—N30.8 (4)
C1—C6—C7—C8177.9 (4)C17—N4—C16—N3179.3 (4)
C5—C6—C7—C12179.4 (4)C15—N4—C16—S1178.2 (3)
C1—C6—C7—C120.3 (4)C17—N4—C16—S11.7 (6)
C12—C7—C8—C91.4 (6)C16—N4—C17—C2268.5 (5)
C6—C7—C8—C9175.9 (4)C15—N4—C17—C22111.6 (5)
C7—C8—C9—C101.1 (7)C16—N4—C17—C18114.9 (5)
C8—C9—C10—C110.0 (7)C15—N4—C17—C1865.0 (5)
C9—C10—C11—C120.7 (7)C22—C17—C18—C191.3 (6)
C10—C11—C12—N1178.5 (4)N4—C17—C18—C19175.3 (4)
C10—C11—C12—C70.4 (6)C17—C18—C19—C201.2 (7)
C1—N1—C12—C11176.5 (4)C18—C19—C20—C210.2 (7)
C13—N1—C12—C1117.1 (7)C19—C20—C21—C221.7 (7)
C1—N1—C12—C72.5 (4)C18—C17—C22—C210.2 (6)
C13—N1—C12—C7161.9 (4)N4—C17—C22—C21176.7 (4)
C8—C7—C12—C110.7 (6)C20—C21—C22—C171.6 (7)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 phenyl ring.
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.95 (5)1.75 (5)2.691 (5)172 (6)
C3—H3···O1i1.01 (5)2.58 (5)3.448 (5)145 (4)
C18—H18···S1ii0.98 (6)2.67 (6)3.645 (4)173 (4)
C5—H5···Cg1iii0.98 (5)2.64 (4)3.422 (4)137 (3)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x1, y, z; (iii) x1/2, 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.

References

First citationBrandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBroadbent, A., Thomas, H. & Broadbent, S. (1998). Curr. Med. Chem. 5, 469–491.  CAS Google Scholar
First citationBruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, R., Yang, X., Tian, H. & Sun, L. (2007). J. Photochem. Photobiol. Chem. 189, 295–300.  CrossRef CAS Google Scholar
First citationCheng, T., Lin, T., Brady, R. & Wang, X. (2008). Fibers Polym. 9, 521–526.  CrossRef CAS Google Scholar
First citationHains, W. & Marks, T. J. (2008). Appl. Phys. Lett. 92, 023504.  CrossRef Google Scholar
First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2009). TWINABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationKumara Swamy, K. C., Bhuvan Kumar, N. N., Balaraman, E. & Pavan Kumar, K. V. P. (2009). Chem. Rev. 109, 2551–2651.  Google Scholar
First citationXia, Y., Fan, C.-D., Zhao, B.-X., Zhao, J., Shin, D.-S. & Miao, J.-Y. (2008). Eur. J. Med. Chem. 43, 2347–2353.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds