5-{[5-(4-Chloro­phen­yl)-3-methyl-1H-pyrazol-1-yl]meth­yl}-1,3,4-oxa­diazole-2(3H)-thione

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Marzouk, A.A.; Hawaiz, F.E.; Abdel-Rahman, H.M.

doi:10.1107/S2414314617001766

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170176

https://doi.org/10.1107/S2414314617001766

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5-{[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]methyl}-1,3,4-oxadiazole-2(3H)-thione

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Adel A. Marzouk,^e Farouq E. Hawaiz ^f ^* and Hamdy M. Abdel-Rahman ^g

^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, ^ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, 71515 Assiut, Egypt, ^fChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq, and ^gFaculty of Pharmacy, Medicinal Chemistry Department, Assiut University, Assiut 71526, Egypt
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 24 January 2017; accepted 1 February 2017; online 3 February 2017)

In the title compound, C₁₃H₁₁ClN₄OS, the oxadiazolethione ring is inclined to the pyrazole ring by 79.2 (2)°. The 4-chlorophenyl ring is rotationally disordered, with the two fragments inclined to one another by 27.1 (4)°, and to the pyrazole ring by 43.1 (3) and 68.6 (3)°. In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds, forming inversion dimers, enclosing an R₂²(14) ring motif. The dimers are linked by C—H⋯N hydrogen bonds, forming ribbons propagating along the a-axis direction and enclosing R₂²(8) ring motifs. The ribbons are linked by C—H⋯Cl hydrogen bonds, forming a three-dimensional supramolecular structure.

Keywords: crystal structure; pyrazole; oxadiazolethione; hydrogen bonding.

CCDC reference: 1530588

Structure description

The pyrazole nucleus is common in a number of biologically active molecules, exhibiting antibacterial (Nada et al., 2009 ), antitubercular (Pattan et al., 2009 ), antidepressant (Mathew et al., 2012 ), anti-inflammatory (El-Moghazy et al., 2012 ), analgesic (Panneer et al., 2011 ), anticancer (Mohareb et al., 2012 ) and antioxidant (Tarun et al., 2012 ) activities. Our research is directed towards the synthesis of novel pyrazole derivatives with good anti-inflammatory activity in good yield. Herein, we report on the synthesis and crystal structure of the title pyrazole derivative.

In the title compound, Fig. 1, the dihedral angle between the mean planes of the two five-membered rings is 79.2 (2)°, while that between the pyrazole ring and the C8A–C13A orientation of the disordered 4-chlorophenyl ring is 43.1 (3)°. The disorder in the benzene ring involves primarily a rotation about the C4—C8 (A or B) bond by 27.1 (4)°, with a nearly equal population in both orientations.

Figure 1
The molecular structure of the title compound, showing the atom labelling and 50% probability displacement ellipsoids. The alternate location of the 4-chlorophenyl ring is shown by pale solid ellipsoids and dotted line bonds.

In the crystal, pairwise N1—H1⋯N4ⁱ and C3—H3B⋯N2ⁱⁱ hydrogen bonds (see Table 1) form ribbons running along the a-axis direction (Fig. 2). The ribbons are connected by pairwise C7—H7C⋯Cl1Bⁱⁱⁱ hydrogen bonds (see Table 1) to form a three-dimensional supramolecular structure (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4ⁱ	0.88	2.02	2.836 (5)	153
C3—H3B⋯N2ⁱⁱ	0.99	2.51	3.445 (6)	158
C7—H7C⋯Cl1Bⁱⁱⁱ	0.98	2.73	3.635 (10)	153
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+2, -z+1; (iii) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
A view of the ribbons formed by N—H⋯N and C—H⋯N hydrogen bonds (dashed lines; see Table 1

). For clarity, only the H atoms involved in hydrogen bonding have been included.

Figure 3
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1

) and, for clarity, only the H atoms involved in hydrogen bonding have been included.

Synthesis and crystallization

A mixture of 2-(5-(4-chlorophenyl)-3-methyl-1H-pyrazol-1-yl)acetic acid hydrazide (1.33 g, 5 mmol) and potassium hydroxide (0.2 g, 5 mmol) in carbon disulfide (5 ml) was refluxed in ethanol (25 ml) for 12 h on a steam bath. The reaction mixture was concentrated, cooled and neutralized with hydrochloric acid solution. The separated solid was collected, washed with water, dried and crystallized from ethanol solution to give colourless needle-like crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The benzene ring (C8–C13) is rotationally disordered by 27.1 (4)° in approximately equal amounts; refined occupancy ratio (A:B) = 0.506 (5): 0.494 (5). The two components of the disordered ring were refined as rigid hexagons.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₁ClN₄OS
M_r	306.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	4.9309 (2), 17.1173 (8), 16.6517 (7)
β (°)	91.189 (3)
V (Å³)	1405.16 (11)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	3.81
Crystal size (mm)	0.20 × 0.05 × 0.02

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.63, 0.92
No. of measured, independent and observed [I > 2σ(I)] reflections	10669, 2632, 1759
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.195, 1.05
No. of reflections	2632
No. of parameters	180
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.49
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) Mercury (Macrae et al., 2008 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1530588

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617001766/su4127sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001766/su4127Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001766/su4127Isup3.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: DIAMOND (Brandenburg & Putz, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

5-{[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]methyl}-1,3,4-oxadiazole-2(3H)-thione top

Crystal data top

C₁₃H₁₁ClN₄OS	F(000) = 632
M_r = 306.77	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 4.9309 (2) Å	Cell parameters from 4259 reflections
b = 17.1173 (8) Å	θ = 3.7–69.9°
c = 16.6517 (7) Å	µ = 3.81 mm⁻¹
β = 91.189 (3)°	T = 150 K
V = 1405.16 (11) Å³	Needles, colourless
Z = 4	0.20 × 0.05 × 0.02 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2632 independent reflections
Radiation source: INCOATEC IµS micro-focus source	1759 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.080
Detector resolution: 10.4167 pixels mm^-1	θ_max = 70.1°, θ_min = 3.7°
ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −20→18
T_min = 0.63, T_max = 0.92	l = −20→20
10669 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.106P)² + 0.4524P] where P = (F_o² + 2F_c²)/3
2632 reflections	(Δ/σ)_max = 0.001
180 parameters	Δρ_max = 0.51 e Å⁻³
2 restraints	Δρ_min = −0.49 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.

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. The 4-chlorophenyl group is rotationally disordered by 27.1 (4)° in approximately equal amounts. The two components of the disorder were refined as rigid hexagons. H-atoms were placed in calculated positions (C—H = 0.95 - 0.9 Å; N—H = 0.88 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	1.3239 (3)	0.90840 (8)	0.71546 (7)	0.0599 (4)
O1	0.9335 (6)	0.86722 (16)	0.60987 (18)	0.0498 (7)
N1	0.9888 (7)	0.9914 (2)	0.6167 (2)	0.0491 (8)
H1	1.0495	1.0379	0.6307	0.059*
N2	0.7856 (7)	0.9795 (2)	0.5597 (2)	0.0482 (8)
N3	0.7160 (7)	0.8117 (2)	0.4491 (2)	0.0489 (9)
N4	0.8597 (7)	0.8490 (2)	0.3914 (2)	0.0511 (9)
C1	1.0829 (8)	0.9253 (2)	0.6482 (2)	0.0473 (10)
C2	0.7581 (8)	0.9051 (2)	0.5581 (3)	0.0476 (10)
C3	0.5703 (9)	0.8592 (3)	0.5072 (3)	0.0556 (11)
H3A	0.4608	0.8246	0.5415	0.067*
H3B	0.4447	0.8950	0.4782	0.067*
C4	0.7085 (9)	0.7334 (3)	0.4378 (3)	0.0526 (11)
C5	0.8504 (10)	0.7191 (3)	0.3686 (3)	0.0564 (12)
H5	0.8798	0.6700	0.3438	0.068*
C6	0.9417 (9)	0.7919 (3)	0.3426 (3)	0.0527 (11)
C7	1.1209 (10)	0.8099 (3)	0.2742 (3)	0.0613 (12)
H7A	1.0721	0.7764	0.2284	0.092*
H7B	1.3103	0.8004	0.2903	0.092*
H7C	1.0983	0.8649	0.2588	0.092*
Cl1A	0.1985 (12)	0.4995 (3)	0.6544 (5)	0.0542 (10)	0.506 (5)
C8A	0.5677 (16)	0.6786 (3)	0.4912 (5)	0.0459 (10)	0.506 (5)
C9A	0.5994 (16)	0.6831 (4)	0.5742 (5)	0.049 (2)	0.506 (5)
H9A	0.6967	0.7255	0.5979	0.059*	0.506 (5)
C10A	0.4886 (18)	0.6258 (5)	0.6227 (3)	0.0514 (17)	0.506 (5)
H10A	0.5102	0.6289	0.6794	0.062*	0.506 (5)
C11A	0.3461 (18)	0.5638 (4)	0.5881 (4)	0.0418 (16)	0.506 (5)
C12A	0.3145 (15)	0.5593 (4)	0.5051 (5)	0.0475 (15)	0.506 (5)
H12A	0.2171	0.5169	0.4815	0.057*	0.506 (5)
C13A	0.4252 (16)	0.6167 (4)	0.4567 (3)	0.0433 (18)	0.506 (5)
H13A	0.4036	0.6136	0.3999	0.052*	0.506 (5)
Cl1B	0.1220 (12)	0.5135 (4)	0.6530 (5)	0.0542 (10)	0.494 (5)
C8B	0.5833 (15)	0.6771 (4)	0.4934 (5)	0.0459 (10)	0.494 (5)
C9B	0.6805 (13)	0.6650 (5)	0.5714 (6)	0.049 (2)	0.494 (5)
H9B	0.8412	0.6906	0.5897	0.059*	0.494 (5)
C10B	0.5427 (17)	0.6154 (5)	0.6226 (4)	0.0514 (17)	0.494 (5)
H10B	0.6091	0.6072	0.6759	0.062*	0.494 (5)
C11B	0.3076 (16)	0.5780 (4)	0.5958 (4)	0.0418 (16)	0.494 (5)
C12B	0.2104 (13)	0.5901 (4)	0.5178 (5)	0.0475 (15)	0.494 (5)
H12B	0.0498	0.5644	0.4995	0.057*	0.494 (5)
C13B	0.3483 (16)	0.6396 (5)	0.4666 (4)	0.0433 (18)	0.494 (5)
H13B	0.2819	0.6479	0.4134	0.052*	0.494 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0586 (7)	0.0667 (8)	0.0547 (6)	0.0081 (5)	0.0091 (5)	0.0061 (5)
O1	0.0478 (16)	0.0355 (15)	0.0665 (19)	0.0006 (12)	0.0149 (14)	−0.0005 (13)
N1	0.055 (2)	0.041 (2)	0.0515 (19)	−0.0032 (16)	0.0035 (17)	−0.0019 (15)
N2	0.051 (2)	0.042 (2)	0.052 (2)	−0.0013 (15)	0.0075 (16)	−0.0023 (14)
N3	0.049 (2)	0.0377 (19)	0.061 (2)	−0.0072 (15)	0.0139 (17)	−0.0069 (15)
N4	0.051 (2)	0.0371 (19)	0.066 (2)	−0.0013 (15)	0.0133 (17)	0.0025 (15)
C1	0.048 (2)	0.042 (2)	0.053 (2)	0.0021 (17)	0.0185 (19)	0.0016 (17)
C2	0.043 (2)	0.042 (2)	0.058 (2)	0.0014 (17)	0.0153 (19)	−0.0005 (18)
C3	0.052 (3)	0.041 (2)	0.074 (3)	−0.0029 (19)	0.014 (2)	−0.012 (2)
C4	0.050 (2)	0.042 (2)	0.066 (3)	−0.0030 (18)	0.013 (2)	−0.0052 (19)
C5	0.060 (3)	0.038 (2)	0.072 (3)	0.0026 (19)	0.023 (2)	−0.004 (2)
C6	0.051 (3)	0.041 (2)	0.066 (3)	−0.0018 (18)	0.015 (2)	0.0029 (19)
C7	0.066 (3)	0.051 (3)	0.068 (3)	0.002 (2)	0.024 (2)	0.009 (2)
Cl1A	0.069 (3)	0.0373 (19)	0.0567 (7)	0.0002 (16)	0.001 (2)	0.0098 (13)
C8A	0.038 (2)	0.036 (2)	0.064 (3)	0.0009 (16)	0.0118 (19)	−0.0029 (18)
C9A	0.025 (5)	0.070 (5)	0.053 (3)	−0.010 (4)	0.023 (3)	−0.023 (3)
C10A	0.036 (4)	0.069 (4)	0.050 (3)	−0.004 (3)	0.009 (2)	−0.008 (2)
C11A	0.046 (3)	0.028 (3)	0.052 (3)	0.007 (3)	0.009 (2)	−0.006 (2)
C12A	0.045 (4)	0.040 (4)	0.058 (4)	−0.003 (3)	0.002 (3)	0.002 (3)
C13A	0.031 (5)	0.040 (5)	0.058 (3)	0.009 (3)	−0.005 (3)	0.008 (3)
Cl1B	0.069 (3)	0.0373 (19)	0.0567 (7)	0.0002 (16)	0.001 (2)	0.0098 (13)
C8B	0.038 (2)	0.036 (2)	0.064 (3)	0.0009 (16)	0.0118 (19)	−0.0029 (18)
C9B	0.025 (5)	0.070 (5)	0.053 (3)	−0.010 (4)	0.023 (3)	−0.023 (3)
C10B	0.036 (4)	0.069 (4)	0.050 (3)	−0.004 (3)	0.009 (2)	−0.008 (2)
C11B	0.046 (3)	0.028 (3)	0.052 (3)	0.007 (3)	0.009 (2)	−0.006 (2)
C12B	0.045 (4)	0.040 (4)	0.058 (4)	−0.003 (3)	0.002 (3)	0.002 (3)
C13B	0.031 (5)	0.040 (5)	0.058 (3)	0.009 (3)	−0.005 (3)	0.008 (3)

Geometric parameters (Å, º) top

S1—C1	1.642 (5)	Cl1A—C11A	1.730 (3)
O1—C2	1.371 (5)	C8A—C9A	1.3900
O1—C1	1.386 (5)	C8A—C13A	1.3900
N1—C1	1.327 (5)	C9A—C10A	1.3900
N1—N2	1.380 (5)	C9A—H9A	0.9500
N1—H1	0.8800	C10A—C11A	1.3900
N2—C2	1.282 (5)	C10A—H10A	0.9500
N3—C4	1.355 (6)	C11A—C12A	1.3900
N3—N4	1.364 (5)	C12A—C13A	1.3900
N3—C3	1.463 (5)	C12A—H12A	0.9500
N4—C6	1.339 (6)	C13A—H13A	0.9500
C2—C3	1.470 (6)	Cl1B—C11B	1.732 (3)
C3—H3A	0.9900	C8B—C9B	1.3900
C3—H3B	0.9900	C8B—C13B	1.3900
C4—C5	1.383 (6)	C9B—C10B	1.3900
C4—C8A	1.476 (5)	C9B—H9B	0.9500
C4—C8B	1.480 (5)	C10B—C11B	1.3900
C5—C6	1.396 (6)	C10B—H10B	0.9500
C5—H5	0.9500	C11B—C12B	1.3900
C6—C7	1.488 (6)	C12B—C13B	1.3900
C7—H7A	0.9800	C12B—H12B	0.9500
C7—H7B	0.9800	C13B—H13B	0.9500
C7—H7C	0.9800

C2—O1—C1	105.8 (3)	H7B—C7—H7C	109.5
C1—N1—N2	112.8 (4)	C9A—C8A—C13A	120.0
C1—N1—H1	123.6	C9A—C8A—C4	121.3 (7)
N2—N1—H1	123.6	C13A—C8A—C4	118.4 (7)
C2—N2—N1	103.7 (3)	C10A—C9A—C8A	120.0
C4—N3—N4	112.2 (3)	C10A—C9A—H9A	120.0
C4—N3—C3	129.0 (4)	C8A—C9A—H9A	120.0
N4—N3—C3	118.4 (3)	C11A—C10A—C9A	120.0
C6—N4—N3	104.8 (3)	C11A—C10A—H10A	120.0
N1—C1—O1	104.6 (4)	C9A—C10A—H10A	120.0
N1—C1—S1	131.5 (4)	C10A—C11A—C12A	120.0
O1—C1—S1	123.9 (3)	C10A—C11A—Cl1A	115.9 (6)
N2—C2—O1	113.0 (4)	C12A—C11A—Cl1A	123.9 (6)
N2—C2—C3	127.5 (4)	C13A—C12A—C11A	120.0
O1—C2—C3	119.5 (4)	C13A—C12A—H12A	120.0
N3—C3—C2	111.5 (4)	C11A—C12A—H12A	120.0
N3—C3—H3A	109.3	C12A—C13A—C8A	120.0
C2—C3—H3A	109.3	C12A—C13A—H13A	120.0
N3—C3—H3B	109.3	C8A—C13A—H13A	120.0
C2—C3—H3B	109.3	C9B—C8B—C13B	120.0
H3A—C3—H3B	108.0	C9B—C8B—C4	122.8 (7)
N3—C4—C5	106.1 (4)	C13B—C8B—C4	117.1 (7)
N3—C4—C8A	123.8 (5)	C8B—C9B—C10B	120.0
C5—C4—C8A	130.0 (5)	C8B—C9B—H9B	120.0
N3—C4—C8B	124.6 (5)	C10B—C9B—H9B	120.0
C5—C4—C8B	129.2 (5)	C11B—C10B—C9B	120.0
C4—C5—C6	105.9 (4)	C11B—C10B—H10B	120.0
C4—C5—H5	127.1	C9B—C10B—H10B	120.0
C6—C5—H5	127.1	C10B—C11B—C12B	120.0
N4—C6—C5	111.1 (4)	C10B—C11B—Cl1B	124.4 (6)
N4—C6—C7	120.3 (4)	C12B—C11B—Cl1B	115.6 (6)
C5—C6—C7	128.5 (4)	C13B—C12B—C11B	120.0
C6—C7—H7A	109.5	C13B—C12B—H12B	120.0
C6—C7—H7B	109.5	C11B—C12B—H12B	120.0
H7A—C7—H7B	109.5	C12B—C13B—C8B	120.0
C6—C7—H7C	109.5	C12B—C13B—H13B	120.0
H7A—C7—H7C	109.5	C8B—C13B—H13B	120.0

C1—N1—N2—C2	0.5 (5)	N3—C4—C8A—C9A	−46.9 (7)
C4—N3—N4—C6	0.5 (5)	C5—C4—C8A—C9A	134.3 (6)
C3—N3—N4—C6	−172.9 (4)	N3—C4—C8A—C13A	140.1 (5)
N2—N1—C1—O1	0.0 (4)	C5—C4—C8A—C13A	−38.8 (9)
N2—N1—C1—S1	178.6 (3)	C13A—C8A—C9A—C10A	0.0
C2—O1—C1—N1	−0.5 (4)	C4—C8A—C9A—C10A	−173.0 (7)
C2—O1—C1—S1	−179.2 (3)	C8A—C9A—C10A—C11A	0.0
N1—N2—C2—O1	−0.8 (4)	C9A—C10A—C11A—C12A	0.0
N1—N2—C2—C3	−179.3 (4)	C9A—C10A—C11A—Cl1A	−175.9 (7)
C1—O1—C2—N2	0.8 (4)	C10A—C11A—C12A—C13A	0.0
C1—O1—C2—C3	179.5 (3)	Cl1A—C11A—C12A—C13A	175.6 (7)
C4—N3—C3—C2	123.0 (5)	C11A—C12A—C13A—C8A	0.0
N4—N3—C3—C2	−64.9 (5)	C9A—C8A—C13A—C12A	0.0
N2—C2—C3—N3	113.1 (5)	C4—C8A—C13A—C12A	173.2 (7)
O1—C2—C3—N3	−65.3 (5)	N3—C4—C8B—C9B	−64.5 (7)
N4—N3—C4—C5	−1.0 (5)	C5—C4—C8B—C9B	111.6 (7)
C3—N3—C4—C5	171.5 (4)	N3—C4—C8B—C13B	111.0 (6)
N4—N3—C4—C8A	179.9 (6)	C5—C4—C8B—C13B	−72.9 (7)
C3—N3—C4—C8A	−7.6 (9)	C13B—C8B—C9B—C10B	0.0
N4—N3—C4—C8B	175.8 (6)	C4—C8B—C9B—C10B	175.4 (7)
C3—N3—C4—C8B	−11.7 (9)	C8B—C9B—C10B—C11B	0.0
N3—C4—C5—C6	1.1 (6)	C9B—C10B—C11B—C12B	0.0
C8A—C4—C5—C6	−179.9 (7)	C9B—C10B—C11B—Cl1B	178.6 (7)
C8B—C4—C5—C6	−175.5 (6)	C10B—C11B—C12B—C13B	0.0
N3—N4—C6—C5	0.3 (5)	Cl1B—C11B—C12B—C13B	−178.7 (7)
N3—N4—C6—C7	−176.2 (4)	C11B—C12B—C13B—C8B	0.0
C4—C5—C6—N4	−0.9 (6)	C9B—C8B—C13B—C12B	0.0
C4—C5—C6—C7	175.3 (5)	C4—C8B—C13B—C12B	−175.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4ⁱ	0.88	2.02	2.836 (5)	153
C3—H3B···N2ⁱⁱ	0.99	2.51	3.445 (6)	158
C7—H7C···Cl1Bⁱⁱⁱ	0.98	2.73	3.635 (10)	153

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

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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