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

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; El-Emary, T.I.; Albayati, M.R.

doi:10.1107/S2414314616018551

organic compounds

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ISSN: 2414-3146

Volume 1| Part 11| November 2016| x161855

https://doi.org/10.1107/S2414314616018551

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

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Talaat I. El-Emary ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^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 M. Weil, Vienna University of Technology, Austria (Received 7 November 2016; accepted 19 November 2016; online 25 November 2016)

In the crystal of the title compound, C₁₆H₁₅N₅S·C₂H₆OS, both the 1,2,4-triazole derivative molecules and the disordered [refined occupancy ratio = 0.604 (1):0.396 (1)] dimethyl sulfoxide solvent molecules form centrosymmetric dimers, by way of pairwise N—H⋯S and C—H⋯O hydrogen bonds, respectively. In the crystal, the two types of dimer are connected by N—H⋯O hydrogen bonds, forming infinite chains parallel to [101]. The packing is assisted by π–π stacking and C—H⋯π(ring) and N—H⋯π(ring) interactions.

Keywords: crystal structure; carbazole; triazole; dimer; hydrogen bonds; π–π stacking.

CCDC reference: 1518058

Structure description

1,2,4-Triazole and its derivatives are found to be associated with various biological activities (Dundar et al., 2007 ). For example, fluconazole is used as an antimicrobial drug, while vorozole, letrozole and anastrozole are non-steroidal and used for the treatment of cancer, and loreclezole is an anticonvulsant (Bekircan & Bektas, 2006 ). Moreover, 4-amino-1,2,4-triazoles are potentially good corrosion inhibitors (Dundar et al., 2007). As part of our studies of triazole derivatives, we report herein the synthesis and crystal structure of the title 1,2,4-triazole derivative.

In the 1,2,4-triazole molecule (Fig. 1), the r.m.s. deviation from planarity of the carbazole moiety is 0.026 Å. The dihedral angle between its mean plane and the plane of the triazole ring is 2.01 (8)°. In the crystal, pairs of these molecules are linked into centrosymmetric dimers by pairs of N—H⋯S hydrogen bonds, giving rise to an R₂²(10) graph-set motif. The dimethyl sulfoxide solvent molecules are linked by pairs of C—H⋯O hydrogen bonds into inversion dimers with a R₂²(8) motif (Table 1, Fig. 2). The two types of dimer are connected by N—H⋯O hydrogen bonds into chains running parallel to [101]. Between the chains, the primary intermolecular interactions are π–π-stacking between the N1/C1/C6/C7/C2 ring and the triazole ring at x, −1 + y, z [centroid-to-centroid distance = 3.443 (1) Å; dihedral angle = 1.7 (1)°] and an offset π–π-stacking between the triazole ring and the C1–C6 ring at x, 1 + y, z [centroid-to-centroid distance = 3.706 (1) Å; dihedral angle = 1.0 (1)°, slippage 1.60 Å]. Additionally, there is a C5—H5⋯π(ring) interaction and an N5—H5A⋯π(ring) interaction (Table 1, Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the six-membered ring of the carbazole moiety.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1Aⁱ	0.91	1.92	2.818 (3)	171
N3—H3A⋯O1Bⁱ	0.91	1.92	2.758 (4)	153
N5—H5B⋯S1ⁱⁱ	0.91	2.51	3.3500 (17)	154
C17A—H17C⋯O1Aⁱⁱⁱ	0.98	2.43	3.242 (15)	140
C5—H5⋯Cg4^iv	0.95	2.54	3.452 (2)	161
N5—H5A⋯Cg4ⁱ	0.91	2.60	3.2718 (18)	131
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The title compound, with the atomic labelling and displacement ellipsoids drawn at the 30% probability level. The minor disorder component of the solvent molecule is not shown.

Figure 2
The packing of the title molecule, viewed along the b axis, showing the N—H⋯S and C—H⋯O interactions. Only the major component of the disordered DMSO solvent molecule is shown and H atoms have been omitted for clarity.

Figure 3
A view of the π–π stacking (purple dotted lines) and C—H⋯π(ring) (green dotted lines) interactions. [Symmetry codes: (i) x, −1 + y, z; (ii) x, 1 + y, z; (iii) $[{1\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z.]

Synthesis and crystallization

A mixture of 3-{2-[4aH-carbazol-9(9aH)-yl]ethyl}-1,2,4-oxadiazole-5-thiol (297 mg, 1 mmol) and an excess of hydrazine in ethanol (10 ml) was refluxed and monitored by TLC until completion. The solid product was collected by filtration and recrystallized from a dimethylsulfoxide solution to afford crystals of the title compound in a quality sufficient for X-ray diffraction measurements.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The solvent molecule was found to be disordered over two sets of sites with a refined ratio of 0.604 (1):0.396 (1). For refinement, restraints were applied so that the geometries of the two components were approximately the same. The (101) reflection was affected by the beam-stop and was omitted from the final cycles of refinement.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₅S·C₂H₆OS
M_r	387.52
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	14.7620 (4), 7.3509 (2), 17.9987 (5)
β (°)	106.936 (1)
V (Å³)	1868.41 (9)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.73
Crystal size (mm)	0.20 × 0.20 × 0.16

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.60, 0.67
No. of measured, independent and observed [I > 2σ(I)] reflections	13596, 3572, 3350
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.125, 1.04
No. of reflections	3572
No. of parameters	248
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.76
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), DIAMOND (Brandenburg & Putz, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1518058

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314616018551/wm4033sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616018551/wm4033Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616018551/wm4033Isup3.cml

checkCIF report

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: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

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

Crystal data top

C₁₆H₁₅N₅S·C₂H₆OS	F(000) = 816
M_r = 387.52	D_x = 1.378 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 14.7620 (4) Å	Cell parameters from 9932 reflections
b = 7.3509 (2) Å	θ = 3.4–72.3°
c = 17.9987 (5) Å	µ = 2.73 mm⁻¹
β = 106.936 (1)°	T = 150 K
V = 1868.41 (9) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.16 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3572 independent reflections
Radiation source: INCOATEC IµS micro-focus source	3350 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.2°, θ_min = 3.4°
ω scans	h = −17→18
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −9→9
T_min = 0.60, T_max = 0.67	l = −22→20
13596 measured reflections

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0676P)² + 1.6793P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3572 reflections	Δρ_max = 0.57 e Å⁻³
248 parameters	Δρ_min = −0.76 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.44681 (3)	0.79061 (6)	0.48603 (3)	0.02910 (16)
N1	0.29032 (11)	−0.0556 (2)	0.60195 (9)	0.0209 (3)
N2	0.22063 (12)	0.4939 (2)	0.46625 (10)	0.0295 (4)
N3	0.27261 (12)	0.6283 (2)	0.44330 (10)	0.0279 (4)
H3A	0.2462	0.7031	0.4025	0.033*
N4	0.36487 (11)	0.5161 (2)	0.54612 (9)	0.0216 (3)
N5	0.44202 (12)	0.4762 (2)	0.61052 (10)	0.0269 (4)
H5A	0.4621	0.5853	0.6333	0.032*
H5B	0.4878	0.4298	0.5914	0.032*
C1	0.20500 (13)	−0.1472 (2)	0.58859 (10)	0.0200 (4)
C2	0.12152 (14)	−0.1248 (3)	0.52883 (11)	0.0259 (4)
H2	0.1165	−0.0362	0.4894	0.031*
C3	0.04597 (15)	−0.2363 (3)	0.52896 (13)	0.0315 (4)
H3	−0.0117	−0.2245	0.4884	0.038*
C4	0.05233 (14)	−0.3661 (3)	0.58726 (13)	0.0312 (5)
H4	−0.0012	−0.4390	0.5862	0.037*
C5	0.13586 (14)	−0.3891 (3)	0.64633 (12)	0.0259 (4)
H5	0.1403	−0.4780	0.6856	0.031*
C6	0.21365 (13)	−0.2795 (2)	0.64734 (10)	0.0197 (4)
C7	0.30950 (13)	−0.2672 (2)	0.69755 (10)	0.0200 (4)
C8	0.36090 (14)	−0.3633 (3)	0.76355 (11)	0.0262 (4)
H8	0.3317	−0.4572	0.7846	0.031*
C9	0.45494 (15)	−0.3189 (3)	0.79747 (12)	0.0322 (5)
H9	0.4905	−0.3832	0.8423	0.039*
C10	0.49835 (14)	−0.1808 (3)	0.76675 (12)	0.0320 (5)
H10	0.5631	−0.1534	0.7911	0.038*
C11	0.44939 (14)	−0.0828 (3)	0.70184 (12)	0.0275 (4)
H11	0.4792	0.0112	0.6813	0.033*
C12	0.35446 (13)	−0.1275 (2)	0.66761 (10)	0.0205 (4)
C13	0.30589 (14)	0.0988 (2)	0.55708 (11)	0.0244 (4)
H13A	0.2786	0.0719	0.5011	0.029*
H13B	0.3748	0.1175	0.5672	0.029*
C14	0.26134 (14)	0.2740 (2)	0.57672 (12)	0.0260 (4)
H14A	0.1923	0.2565	0.5663	0.031*
H14B	0.2886	0.3022	0.6326	0.031*
C15	0.27912 (13)	0.4284 (2)	0.52932 (11)	0.0228 (4)
C16	0.36048 (14)	0.6464 (2)	0.49055 (11)	0.0233 (4)
S2A	0.20345 (6)	0.06746 (11)	0.34615 (5)	0.0318 (2)	0.6038 (10)
O1A	0.20930 (19)	−0.1242 (3)	0.31940 (15)	0.0372 (6)	0.6038 (10)
C17A	0.3100 (5)	0.1801 (13)	0.3459 (10)	0.0372 (5)	0.6038 (10)
H17A	0.3082	0.3061	0.3632	0.056*	0.6038 (10)
H17B	0.3641	0.1171	0.3812	0.056*	0.6038 (10)
H17C	0.3164	0.1792	0.2932	0.056*	0.6038 (10)
C18A	0.1235 (4)	0.1867 (10)	0.2692 (10)	0.0494 (18)	0.6038 (10)
H18A	0.1182	0.3129	0.2850	0.074*	0.6038 (10)
H18B	0.1468	0.1851	0.2235	0.074*	0.6038 (10)
H18C	0.0612	0.1284	0.2565	0.074*	0.6038 (10)
S2B	0.21829 (9)	0.05075 (17)	0.29873 (8)	0.0318 (2)	0.3962 (10)
O1B	0.1936 (3)	−0.0693 (5)	0.3583 (2)	0.0372 (6)	0.3962 (10)
C17B	0.3171 (8)	0.185 (2)	0.3500 (15)	0.0372 (5)	0.3962 (10)
H17D	0.3356	0.2655	0.3135	0.056*	0.3962 (10)
H17E	0.2998	0.2586	0.3892	0.056*	0.3962 (10)
H17F	0.3702	0.1053	0.3755	0.056*	0.3962 (10)
C18B	0.1314 (6)	0.2245 (18)	0.2758 (16)	0.0494 (18)	0.3962 (10)
H18D	0.1441	0.3067	0.2372	0.074*	0.3962 (10)
H18E	0.0686	0.1697	0.2547	0.074*	0.3962 (10)
H18F	0.1333	0.2931	0.3229	0.074*	0.3962 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0326 (3)	0.0194 (3)	0.0406 (3)	−0.00384 (17)	0.0189 (2)	−0.00093 (18)
N1	0.0257 (8)	0.0148 (7)	0.0238 (8)	−0.0011 (6)	0.0096 (6)	0.0035 (6)
N2	0.0305 (9)	0.0185 (8)	0.0378 (9)	−0.0036 (6)	0.0075 (7)	0.0033 (7)
N3	0.0322 (9)	0.0184 (8)	0.0316 (9)	−0.0024 (6)	0.0069 (7)	0.0046 (6)
N4	0.0246 (8)	0.0159 (7)	0.0255 (8)	0.0000 (6)	0.0090 (6)	0.0004 (6)
N5	0.0272 (8)	0.0247 (8)	0.0275 (8)	0.0031 (6)	0.0062 (7)	−0.0011 (6)
C1	0.0258 (9)	0.0145 (8)	0.0210 (8)	−0.0001 (7)	0.0088 (7)	−0.0007 (6)
C2	0.0307 (10)	0.0197 (9)	0.0255 (9)	0.0023 (7)	0.0054 (8)	0.0018 (7)
C3	0.0274 (10)	0.0267 (10)	0.0356 (11)	0.0001 (8)	0.0016 (8)	−0.0027 (8)
C4	0.0283 (10)	0.0254 (10)	0.0405 (11)	−0.0076 (8)	0.0111 (9)	−0.0034 (8)
C5	0.0311 (10)	0.0186 (9)	0.0310 (10)	−0.0034 (7)	0.0136 (8)	0.0004 (7)
C6	0.0262 (9)	0.0135 (8)	0.0211 (8)	0.0001 (6)	0.0097 (7)	−0.0005 (6)
C7	0.0264 (9)	0.0159 (8)	0.0193 (8)	0.0014 (7)	0.0093 (7)	−0.0012 (6)
C8	0.0364 (10)	0.0225 (9)	0.0208 (9)	0.0051 (8)	0.0103 (8)	0.0023 (7)
C9	0.0358 (11)	0.0339 (11)	0.0235 (9)	0.0115 (9)	0.0034 (8)	−0.0004 (8)
C10	0.0246 (9)	0.0359 (11)	0.0334 (11)	0.0032 (8)	0.0052 (8)	−0.0080 (9)
C11	0.0255 (9)	0.0255 (10)	0.0333 (10)	−0.0024 (8)	0.0113 (8)	−0.0048 (8)
C12	0.0241 (9)	0.0167 (8)	0.0221 (8)	0.0010 (7)	0.0088 (7)	−0.0023 (7)
C13	0.0352 (10)	0.0146 (8)	0.0281 (9)	−0.0004 (7)	0.0165 (8)	0.0033 (7)
C14	0.0311 (10)	0.0159 (9)	0.0351 (10)	−0.0005 (7)	0.0162 (8)	0.0016 (7)
C15	0.0253 (9)	0.0138 (8)	0.0317 (10)	−0.0003 (7)	0.0118 (8)	−0.0014 (7)
C16	0.0305 (9)	0.0152 (8)	0.0274 (9)	0.0011 (7)	0.0138 (8)	−0.0019 (7)
S2A	0.0371 (4)	0.0254 (4)	0.0298 (4)	−0.0003 (3)	0.0050 (3)	0.0024 (3)
O1A	0.0453 (12)	0.0199 (12)	0.0377 (14)	−0.0026 (9)	−0.0016 (11)	0.0041 (9)
C17A	0.0335 (14)	0.0370 (13)	0.0405 (17)	−0.0039 (10)	0.0097 (13)	0.0086 (12)
C18A	0.0376 (16)	0.037 (4)	0.064 (3)	−0.0008 (19)	−0.0012 (19)	0.020 (4)
S2B	0.0371 (4)	0.0254 (4)	0.0298 (4)	−0.0003 (3)	0.0050 (3)	0.0024 (3)
O1B	0.0453 (12)	0.0199 (12)	0.0377 (14)	−0.0026 (9)	−0.0016 (11)	0.0041 (9)
C17B	0.0335 (14)	0.0370 (13)	0.0405 (17)	−0.0039 (10)	0.0097 (13)	0.0086 (12)
C18B	0.0376 (16)	0.037 (4)	0.064 (3)	−0.0008 (19)	−0.0012 (19)	0.020 (4)

Geometric parameters (Å, º) top

S1—C16	1.6776 (19)	C9—H9	0.9500
N1—C1	1.386 (2)	C10—C11	1.383 (3)
N1—C12	1.386 (2)	C10—H10	0.9500
N1—C13	1.450 (2)	C11—C12	1.396 (3)
N2—C15	1.302 (3)	C11—H11	0.9500
N2—N3	1.386 (2)	C13—C14	1.533 (3)
N3—C16	1.334 (3)	C13—H13A	0.9900
N3—H3A	0.9100	C13—H13B	0.9900
N4—C16	1.373 (2)	C14—C15	1.488 (3)
N4—C15	1.373 (2)	C14—H14A	0.9900
N4—N5	1.399 (2)	C14—H14B	0.9900
N5—H5A	0.9100	S2A—O1A	1.500 (2)
N5—H5B	0.9100	S2A—C18A	1.768 (7)
C1—C2	1.390 (3)	S2A—C17A	1.778 (7)
C1—C6	1.415 (2)	C17A—H17A	0.9800
C2—C3	1.385 (3)	C17A—H17B	0.9800
C2—H2	0.9500	C17A—H17C	0.9800
C3—C4	1.401 (3)	C18A—H18A	0.9800
C3—H3	0.9500	C18A—H18B	0.9800
C4—C5	1.384 (3)	C18A—H18C	0.9800
C4—H4	0.9500	S2B—O1B	1.512 (3)
C5—C6	1.399 (3)	S2B—C18B	1.772 (8)
C5—H5	0.9500	S2B—C17B	1.781 (8)
C6—C7	1.443 (3)	C17B—H17D	0.9800
C7—C8	1.400 (3)	C17B—H17E	0.9800
C7—C12	1.412 (2)	C17B—H17F	0.9800
C8—C9	1.383 (3)	C18B—H18D	0.9800
C8—H8	0.9500	C18B—H18E	0.9800
C9—C10	1.398 (3)	C18B—H18F	0.9800

C1—N1—C12	108.88 (14)	N1—C13—C14	112.40 (15)
C1—N1—C13	124.54 (15)	N1—C13—H13A	109.1
C12—N1—C13	126.43 (16)	C14—C13—H13A	109.1
C15—N2—N3	103.85 (16)	N1—C13—H13B	109.1
C16—N3—N2	113.64 (16)	C14—C13—H13B	109.1
C16—N3—H3A	124.3	H13A—C13—H13B	107.9
N2—N3—H3A	121.8	C15—C14—C13	110.45 (15)
C16—N4—C15	108.80 (16)	C15—C14—H14A	109.6
C16—N4—N5	127.16 (16)	C13—C14—H14A	109.6
C15—N4—N5	124.04 (15)	C15—C14—H14B	109.6
N4—N5—H5A	105.5	C13—C14—H14B	109.6
N4—N5—H5B	106.2	H14A—C14—H14B	108.1
H5A—N5—H5B	108.7	N2—C15—N4	110.67 (16)
N1—C1—C2	129.28 (17)	N2—C15—C14	126.79 (17)
N1—C1—C6	108.93 (15)	N4—C15—C14	122.47 (17)
C2—C1—C6	121.78 (17)	N3—C16—N4	103.03 (16)
C3—C2—C1	117.48 (18)	N3—C16—S1	130.04 (15)
C3—C2—H2	121.3	N4—C16—S1	126.93 (15)
C1—C2—H2	121.3	O1A—S2A—C18A	107.6 (5)
C2—C3—C4	121.76 (19)	O1A—S2A—C17A	107.6 (6)
C2—C3—H3	119.1	C18A—S2A—C17A	99.0 (4)
C4—C3—H3	119.1	S2A—C17A—H17A	109.5
C5—C4—C3	120.59 (18)	S2A—C17A—H17B	109.5
C5—C4—H4	119.7	H17A—C17A—H17B	109.5
C3—C4—H4	119.7	S2A—C17A—H17C	109.5
C4—C5—C6	118.93 (18)	H17A—C17A—H17C	109.5
C4—C5—H5	120.5	H17B—C17A—H17C	109.5
C6—C5—H5	120.5	S2A—C18A—H18A	109.5
C5—C6—C1	119.44 (17)	S2A—C18A—H18B	109.5
C5—C6—C7	134.08 (17)	H18A—C18A—H18B	109.5
C1—C6—C7	106.48 (15)	S2A—C18A—H18C	109.5
C8—C7—C12	119.46 (17)	H18A—C18A—H18C	109.5
C8—C7—C6	133.64 (17)	H18B—C18A—H18C	109.5
C12—C7—C6	106.89 (15)	O1B—S2B—C18B	106.1 (6)
C9—C8—C7	118.81 (19)	O1B—S2B—C17B	106.7 (7)
C9—C8—H8	120.6	C18B—S2B—C17B	98.6 (5)
C7—C8—H8	120.6	S2B—C17B—H17D	109.5
C8—C9—C10	120.90 (19)	S2B—C17B—H17E	109.5
C8—C9—H9	119.6	H17D—C17B—H17E	109.5
C10—C9—H9	119.6	S2B—C17B—H17F	109.5
C11—C10—C9	121.68 (19)	H17D—C17B—H17F	109.5
C11—C10—H10	119.2	H17E—C17B—H17F	109.5
C9—C10—H10	119.2	S2B—C18B—H18D	109.5
C10—C11—C12	117.43 (19)	S2B—C18B—H18E	109.5
C10—C11—H11	121.3	H18D—C18B—H18E	109.5
C12—C11—H11	121.3	S2B—C18B—H18F	109.5
N1—C12—C11	129.45 (17)	H18D—C18B—H18F	109.5
N1—C12—C7	108.81 (15)	H18E—C18B—H18F	109.5
C11—C12—C7	121.72 (17)

C15—N2—N3—C16	−0.2 (2)	C13—N1—C12—C11	−6.5 (3)
C12—N1—C1—C2	−178.40 (18)	C1—N1—C12—C7	−0.4 (2)
C13—N1—C1—C2	5.8 (3)	C13—N1—C12—C7	175.25 (16)
C12—N1—C1—C6	0.7 (2)	C10—C11—C12—N1	−178.21 (18)
C13—N1—C1—C6	−175.03 (15)	C10—C11—C12—C7	−0.1 (3)
N1—C1—C2—C3	179.56 (18)	C8—C7—C12—N1	178.85 (16)
C6—C1—C2—C3	0.5 (3)	C6—C7—C12—N1	−0.05 (19)
C1—C2—C3—C4	0.6 (3)	C8—C7—C12—C11	0.4 (3)
C2—C3—C4—C5	−1.2 (3)	C6—C7—C12—C11	−178.51 (17)
C3—C4—C5—C6	0.6 (3)	C1—N1—C13—C14	75.0 (2)
C4—C5—C6—C1	0.5 (3)	C12—N1—C13—C14	−100.0 (2)
C4—C5—C6—C7	−178.90 (19)	N1—C13—C14—C15	−179.99 (15)
N1—C1—C6—C5	179.69 (16)	N3—N2—C15—N4	−0.2 (2)
C2—C1—C6—C5	−1.1 (3)	N3—N2—C15—C14	−177.15 (18)
N1—C1—C6—C7	−0.75 (19)	C16—N4—C15—N2	0.4 (2)
C2—C1—C6—C7	178.46 (17)	N5—N4—C15—N2	179.78 (16)
C5—C6—C7—C8	1.3 (4)	C16—N4—C15—C14	177.57 (16)
C1—C6—C7—C8	−178.19 (19)	N5—N4—C15—C14	−3.1 (3)
C5—C6—C7—C12	179.95 (19)	C13—C14—C15—N2	99.2 (2)
C1—C6—C7—C12	0.49 (19)	C13—C14—C15—N4	−77.4 (2)
C12—C7—C8—C9	−0.3 (3)	N2—N3—C16—N4	0.4 (2)
C6—C7—C8—C9	178.20 (19)	N2—N3—C16—S1	−179.43 (14)
C7—C8—C9—C10	0.0 (3)	C15—N4—C16—N3	−0.49 (19)
C8—C9—C10—C11	0.3 (3)	N5—N4—C16—N3	−179.81 (16)
C9—C10—C11—C12	−0.2 (3)	C15—N4—C16—S1	179.35 (14)
C1—N1—C12—C11	177.88 (18)	N5—N4—C16—S1	0.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the six-membered ring of the carbazole moiety.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1Aⁱ	0.91	1.92	2.818 (3)	171
N3—H3A···O1Bⁱ	0.91	1.92	2.758 (4)	153
N5—H5B···S1ⁱⁱ	0.91	2.51	3.3500 (17)	154
C17A—H17C···O1Aⁱⁱⁱ	0.98	2.43	3.242 (15)	140
C5—H5···Cg4^iv	0.95	2.54	3.452 (2)	161
N5—H5A···Cg4ⁱ	0.91	2.60	3.2718 (18)	131

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+3/2.

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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