N′-[5-Acetyl-3-(4-chloro­phen­yl)-2,3-di­hydro-1,3,4-thia­diazol-2-yl­idene]-5-(1H-indol-3-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide di­methyl­formamide monosolvate

El-Hiti, G.A.; Abdel-Wahab, B.F.; Yousif, E.; Alotaibi, M.H.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314619001482

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 1| January 2019| x190148

https://doi.org/10.1107/S2414314619001482

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N′-[5-Acetyl-3-(4-chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]-5-(1H-indol-3-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide dimethylformamide monosolvate

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Emad Yousif,^d Mohammad Hayal Alotaibi,^e Amany S. Hegazy ^f and Benson M. Kariuki ^f ‡

^aDepartment of Optometry, College of Applied Medical Sciences, King Saud, University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt, ^dDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq, ^eNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and ^fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 22 January 2019; accepted 25 January 2019; online 31 January 2019)

In the title solvate, C₂₈H₂₀ClN₇O₂S·C₃H₇NO, the main molecule consists of chlorophenyl (A), thiadiazolyl (B), pyrazolyl (C), phenyl (D) and indolyl (E) rings, with twist angles between neighbouring rings A/B, B/C, C/D and D/E of 32.6 (1), 14.8 (1), 60.8 (1) and 20.1 (1)°, respectively. The dimethylformamide solvent molecule accepts an N—H⋯O hydrogen bond from the indole group. In the extended structure, molecules related by 2₁ screw axes are stacked in the [001] direction to form columns linked by weak C—H⋯O interactions.

Keywords: crystal structure; thiadiazole; indole; hydrogen bonds.

CCDC reference: 1893639

Structure description

1,3,4-Thiadiazoles have various biological properties including anticancer, diuretic, antibacterial and antifungal activities (Dawood & Farghaly, 2017 ; Li et al., 2013 ; Lv et al., 2018 ; Matysiak 2015 ; Serban et al., 2018 ). As part of our work in this area, we now describe the structure of the title compound.

The asymmetric unit consists of the one molecule of C₂₈H₂₀ClN₇O₂S and a molecule of dimethylformamide solvent (Fig. 1). The main molecule features chlorophenyl (A), thiadiazolyl (B), pyrazolyl (C), phenyl (D) and indolyl (E) rings. The twist angles between the planes through the neighbouring ring pairs A/B, B/C, C/D and D/E are 32.6 (1), 14.8 (1), 60.8 (1) and 20.1 (1)°, respectively. The dimethylformamide solvent accepts an N—H⋯O hydrogen bond from the indole group. In the extended structure (Fig. 2), molecules related by a 2₁ screw axes are stacked in the [001] direction to form columns linked by weak C—H⋯O interactions (Table 1, Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7A⋯O3	0.86	1.96	2.784 (4)	159
C16—H16⋯O2ⁱ	0.93	2.34	3.258 (5)	168
Symmetry code: (i) $[-x, -y+1, z-{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound showing 50% displacement ellipsoids.

Figure 2
The crystal structure viewed down the c-axis direction.

Figure 3
A segment of the crystal structure showing C—H⋯O contacts as dotted lines.

Synthesis and crystallization

The title compound was synthesized as previously reported (Abdel-Gawad et al., 2010 ) from the reaction of potassium 2-(5-(1H-indol-3-yl)-1-phenyl-1H-pyrazole-3-carbonyl)hydrazinecarbodithioate and N′-(4-chlorophenyl)-2-oxopropanehydrazonoyl chloride in ethanol under reflux for 2 h. The solid produced was collected by filtration, washed with ethanol, dried and recrystallized from dimethylformamide solution to give pale-yellow needles (m.p. 257–258°C; Abdel-Gawad et al., 2010).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₈H₂₀ClN₇O₂S·C₃H₇NO
M_r	627.11
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	22.6215 (9), 18.1779 (7), 7.5064 (4)
V (Å³)	3086.7 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.55 × 0.07 × 0.03

Data collection
Diffractometer	Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.680, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	28180, 7744, 4455
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.702

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.120, 1.01
No. of reflections	7744
No. of parameters	400
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.22
Absolute structure	Flack x determined using 1442 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.00 (3)
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1893639

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001482/hb4281sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619001482/hb4281Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619001482/hb4281Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2001).

N'-[5-Acetyl-3-(4-chlorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-ylidene]-5-(1H-indol-3-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide dimethylformamide monosolvate top

Crystal data top

C₂₈H₂₀ClN₇O₂S·C₃H₇NO	D_x = 1.349 Mg m⁻³
M_r = 627.11	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 6090 reflections
a = 22.6215 (9) Å	θ = 3.2–23.1°
b = 18.1779 (7) Å	µ = 0.24 mm⁻¹
c = 7.5064 (4) Å	T = 293 K
V = 3086.7 (2) Å³	Needle, yellow
Z = 4	0.55 × 0.07 × 0.03 mm
F(000) = 1304

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	4455 reflections with I > 2σ(I)
ω scans	R_int = 0.044
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 29.9°, θ_min = 2.9°
T_min = 0.680, T_max = 1.000	h = −31→30
28180 measured reflections	k = −18→25
7744 independent reflections	l = −10→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0542P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.120	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.15 e Å⁻³
7744 reflections	Δρ_min = −0.22 e Å⁻³
400 parameters	Absolute structure: Flack x determined using 1442 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.00 (3)
Primary atom site location: structure-invariant direct methods

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
C1	0.1098 (2)	0.9233 (2)	0.8123 (8)	0.0857 (14)
H1A	0.145169	0.940879	0.868732	0.129*
H1B	0.076119	0.936566	0.883041	0.129*
H1C	0.106292	0.944924	0.696124	0.129*
C2	0.11270 (18)	0.8422 (2)	0.7952 (6)	0.0675 (11)
C3	0.05800 (16)	0.80099 (18)	0.7611 (6)	0.0567 (9)
C4	−0.01539 (14)	0.70568 (16)	0.7047 (5)	0.0488 (9)
C5	−0.09404 (14)	0.80336 (16)	0.6647 (5)	0.0506 (8)
C6	−0.14215 (14)	0.76154 (18)	0.7133 (5)	0.0555 (9)
H6	−0.136790	0.717086	0.772523	0.067*
C7	−0.19860 (15)	0.7862 (2)	0.6735 (6)	0.0619 (9)
H7	−0.231393	0.758786	0.708078	0.074*
C8	−0.20590 (17)	0.8511 (2)	0.5830 (6)	0.0679 (11)
C9	−0.15788 (19)	0.8933 (2)	0.5380 (7)	0.0776 (12)
H9	−0.163285	0.938020	0.479824	0.093*
C10	−0.10161 (18)	0.86951 (19)	0.5790 (6)	0.0673 (11)
H10	−0.068979	0.898050	0.548954	0.081*
C11	−0.05112 (14)	0.52085 (17)	0.6746 (5)	0.0539 (9)
C12	−0.01367 (13)	0.45389 (16)	0.6807 (5)	0.0516 (8)
C13	−0.03199 (13)	0.38113 (16)	0.6942 (5)	0.0506 (8)
H13	−0.070676	0.364216	0.703290	0.061*
C14	0.01868 (13)	0.33909 (16)	0.6913 (5)	0.0474 (8)
C15	0.12696 (13)	0.37600 (16)	0.6697 (5)	0.0483 (8)
C16	0.15622 (15)	0.39812 (19)	0.5195 (6)	0.0589 (9)
H16	0.136554	0.423826	0.430246	0.071*
C17	0.21581 (15)	0.3814 (2)	0.5029 (7)	0.0690 (11)
H17	0.236128	0.395727	0.400895	0.083*
C18	0.24476 (16)	0.3447 (2)	0.6329 (6)	0.0676 (11)
H18	0.284610	0.333469	0.619426	0.081*
C19	0.21521 (15)	0.3240 (2)	0.7853 (6)	0.0692 (11)
H19	0.235245	0.299127	0.875178	0.083*
C20	0.15557 (15)	0.34016 (19)	0.8050 (6)	0.0604 (10)
H20	0.135437	0.326888	0.908124	0.073*
C21	0.02495 (12)	0.25928 (16)	0.6900 (5)	0.0463 (8)
C22	0.07209 (14)	0.21870 (17)	0.6302 (5)	0.0525 (9)
H22	0.107494	0.238530	0.589491	0.063*
C23	−0.02010 (13)	0.20643 (16)	0.7389 (5)	0.0484 (8)
C24	0.00442 (14)	0.13629 (16)	0.7063 (5)	0.0522 (9)
C25	−0.02642 (17)	0.07159 (19)	0.7409 (7)	0.0699 (11)
H25	−0.009464	0.025957	0.717960	0.084*
C26	−0.08222 (19)	0.0768 (2)	0.8095 (7)	0.0757 (12)
H26	−0.103566	0.034306	0.834845	0.091*
C27	−0.10718 (17)	0.1456 (2)	0.8414 (6)	0.0709 (11)
H27	−0.145400	0.148244	0.886560	0.085*
C28	−0.07684 (15)	0.2098 (2)	0.8079 (5)	0.0583 (9)
H28	−0.094320	0.255062	0.831386	0.070*
C29	0.30679 (19)	0.1233 (3)	0.5200 (10)	0.1075 (18)
H29A	0.294325	0.171195	0.558395	0.161*
H29B	0.324845	0.126931	0.404556	0.161*
H29C	0.334853	0.103758	0.603447	0.161*
C30	0.26488 (19)	0.0004 (3)	0.4550 (8)	0.106 (2)
H30A	0.227503	−0.020796	0.422718	0.158*
H30B	0.281905	−0.027261	0.551141	0.158*
H30C	0.290980	−0.000871	0.354204	0.158*
C31	0.20302 (18)	0.0981 (2)	0.5531 (6)	0.0693 (11)
H31	0.199260	0.146797	0.589274	0.083*
N1	0.00705 (12)	0.83077 (14)	0.7353 (5)	0.0554 (7)
N2	−0.03511 (11)	0.77894 (13)	0.7037 (4)	0.0511 (7)
N3	−0.04906 (11)	0.65123 (14)	0.6751 (5)	0.0562 (8)
N4	−0.02058 (12)	0.58393 (13)	0.6786 (5)	0.0620 (8)
H4	0.017390	0.582558	0.683465	0.074*
N5	0.04496 (11)	0.45956 (13)	0.6727 (5)	0.0551 (7)
N6	0.06430 (10)	0.38905 (13)	0.6820 (4)	0.0502 (7)
N7	0.06004 (12)	0.14612 (14)	0.6385 (4)	0.0562 (8)
H7A	0.083603	0.111452	0.606301	0.067*
N8	0.25628 (13)	0.07514 (17)	0.5102 (5)	0.0706 (10)
O1	0.15870 (13)	0.80757 (17)	0.8054 (6)	0.0978 (11)
O2	−0.10500 (10)	0.51750 (12)	0.6691 (4)	0.0731 (8)
O3	0.15779 (12)	0.06068 (14)	0.5494 (5)	0.0809 (9)
S1	0.06085 (4)	0.70530 (5)	0.75099 (16)	0.0626 (3)
Cl1	−0.27630 (6)	0.88036 (9)	0.5237 (2)	0.1127 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.091 (3)	0.069 (3)	0.097 (4)	−0.017 (2)	−0.002 (3)	−0.007 (3)
C2	0.066 (2)	0.066 (2)	0.070 (3)	−0.008 (2)	−0.007 (2)	0.003 (2)
C3	0.062 (2)	0.0550 (18)	0.054 (2)	−0.0037 (17)	0.0004 (18)	0.0022 (19)
C4	0.0536 (18)	0.0422 (16)	0.051 (2)	0.0056 (14)	0.0022 (17)	0.0007 (15)
C5	0.0565 (19)	0.0464 (17)	0.049 (2)	0.0062 (16)	0.0009 (17)	−0.0025 (16)
C6	0.0573 (19)	0.0480 (17)	0.061 (3)	0.0035 (16)	0.0011 (18)	−0.0015 (17)
C7	0.0540 (18)	0.066 (2)	0.066 (3)	0.0041 (17)	0.0029 (19)	−0.009 (2)
C8	0.066 (2)	0.070 (2)	0.068 (3)	0.019 (2)	−0.003 (2)	0.002 (2)
C9	0.083 (3)	0.069 (2)	0.081 (3)	0.019 (2)	−0.002 (3)	0.023 (2)
C10	0.070 (2)	0.055 (2)	0.077 (3)	0.0043 (18)	0.005 (2)	0.013 (2)
C11	0.0506 (19)	0.0477 (18)	0.064 (2)	0.0057 (15)	−0.0025 (18)	−0.0093 (17)
C12	0.0461 (16)	0.0459 (16)	0.063 (2)	0.0030 (14)	−0.0017 (17)	−0.0093 (17)
C13	0.0431 (16)	0.0480 (17)	0.061 (2)	−0.0013 (14)	−0.0033 (17)	−0.0078 (17)
C14	0.0445 (16)	0.0442 (15)	0.054 (2)	0.0010 (13)	−0.0008 (16)	−0.0017 (16)
C15	0.0417 (15)	0.0418 (15)	0.061 (2)	−0.0003 (13)	0.0001 (17)	−0.0044 (16)
C16	0.0539 (19)	0.060 (2)	0.063 (3)	−0.0006 (17)	−0.0038 (19)	0.0059 (19)
C17	0.051 (2)	0.089 (3)	0.067 (3)	−0.001 (2)	0.008 (2)	0.005 (2)
C18	0.0440 (18)	0.078 (2)	0.081 (3)	0.0052 (19)	−0.001 (2)	−0.007 (2)
C19	0.048 (2)	0.081 (3)	0.079 (3)	0.0056 (18)	−0.008 (2)	0.011 (2)
C20	0.0514 (19)	0.066 (2)	0.063 (3)	−0.0034 (17)	−0.0002 (18)	0.010 (2)
C21	0.0416 (16)	0.0460 (15)	0.051 (2)	0.0016 (13)	−0.0033 (15)	−0.0019 (16)
C22	0.0491 (18)	0.0454 (17)	0.063 (3)	−0.0002 (15)	0.0010 (17)	−0.0017 (17)
C23	0.0470 (17)	0.0493 (16)	0.049 (2)	0.0000 (14)	−0.0082 (16)	−0.0009 (16)
C24	0.0543 (18)	0.0475 (17)	0.055 (2)	−0.0001 (15)	−0.0093 (17)	0.0039 (16)
C25	0.073 (2)	0.0526 (19)	0.084 (3)	−0.0070 (18)	−0.019 (2)	0.008 (2)
C26	0.070 (3)	0.073 (3)	0.084 (3)	−0.028 (2)	−0.013 (2)	0.016 (2)
C27	0.052 (2)	0.089 (3)	0.072 (3)	−0.017 (2)	−0.001 (2)	0.009 (2)
C28	0.0503 (19)	0.066 (2)	0.059 (3)	−0.0007 (17)	−0.0022 (17)	0.0027 (19)
C29	0.062 (2)	0.110 (4)	0.150 (5)	−0.022 (3)	−0.017 (3)	0.012 (4)
C30	0.076 (3)	0.087 (3)	0.153 (6)	0.021 (3)	0.011 (3)	−0.030 (3)
C31	0.067 (2)	0.056 (2)	0.085 (3)	0.007 (2)	0.000 (2)	−0.006 (2)
N1	0.0591 (17)	0.0492 (14)	0.058 (2)	−0.0060 (14)	0.0017 (16)	−0.0008 (15)
N2	0.0511 (15)	0.0422 (13)	0.060 (2)	0.0003 (12)	0.0016 (14)	0.0018 (13)
N3	0.0516 (15)	0.0432 (14)	0.074 (2)	0.0075 (13)	0.0011 (15)	−0.0041 (15)
N4	0.0475 (15)	0.0443 (15)	0.094 (3)	0.0061 (12)	−0.0014 (17)	−0.0041 (16)
N5	0.0467 (14)	0.0418 (13)	0.077 (2)	0.0045 (12)	−0.0045 (15)	−0.0022 (15)
N6	0.0384 (13)	0.0430 (14)	0.069 (2)	0.0023 (11)	0.0006 (14)	−0.0020 (14)
N7	0.0544 (16)	0.0423 (15)	0.072 (2)	0.0048 (12)	−0.0022 (15)	−0.0033 (14)
N8	0.0493 (17)	0.067 (2)	0.096 (3)	0.0039 (15)	−0.0039 (18)	0.0025 (19)
O1	0.0677 (17)	0.092 (2)	0.134 (3)	−0.0053 (16)	−0.0293 (19)	0.000 (2)
O2	0.0492 (14)	0.0555 (13)	0.115 (2)	0.0061 (11)	−0.0040 (15)	−0.0209 (15)
O3	0.0562 (14)	0.0685 (16)	0.118 (3)	−0.0029 (13)	0.0097 (16)	−0.0074 (17)
S1	0.0539 (5)	0.0542 (5)	0.0796 (7)	0.0026 (4)	−0.0076 (5)	0.0075 (5)
Cl1	0.0803 (7)	0.1358 (11)	0.1221 (12)	0.0411 (8)	−0.0190 (8)	0.0142 (10)

Geometric parameters (Å, º) top

C1—C2	1.481 (5)	C17—H17	0.9300
C1—H1A	0.9600	C18—C19	1.378 (6)
C1—H1B	0.9600	C18—H18	0.9300
C1—H1C	0.9600	C19—C20	1.389 (5)
C2—O1	1.218 (5)	C19—H19	0.9300
C2—C3	1.469 (5)	C20—H20	0.9300
C3—N1	1.288 (4)	C21—C22	1.372 (4)
C3—S1	1.742 (3)	C21—C23	1.448 (4)
C4—N3	1.268 (4)	C22—N7	1.349 (4)
C4—N2	1.404 (4)	C22—H22	0.9300
C4—S1	1.759 (3)	C23—C28	1.385 (5)
C5—C10	1.374 (5)	C23—C24	1.412 (4)
C5—C6	1.377 (5)	C24—N7	1.369 (4)
C5—N2	1.435 (4)	C24—C25	1.392 (5)
C6—C7	1.386 (5)	C25—C26	1.366 (6)
C6—H6	0.9300	C25—H25	0.9300
C7—C8	1.372 (6)	C26—C27	1.393 (6)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.373 (6)	C27—C28	1.377 (5)
C8—Cl1	1.737 (4)	C27—H27	0.9300
C9—C10	1.380 (6)	C28—H28	0.9300
C9—H9	0.9300	C29—N8	1.441 (5)
C10—H10	0.9300	C29—H29A	0.9600
C11—O2	1.221 (4)	C29—H29B	0.9600
C11—N4	1.339 (4)	C29—H29C	0.9600
C11—C12	1.484 (4)	C30—N8	1.434 (6)
C12—N5	1.331 (4)	C30—H30A	0.9600
C12—C13	1.390 (4)	C30—H30B	0.9600
C13—C14	1.378 (4)	C30—H30C	0.9600
C13—H13	0.9300	C31—O3	1.229 (5)
C14—N6	1.376 (4)	C31—N8	1.315 (5)
C14—C21	1.458 (4)	C31—H31	0.9300
C15—C16	1.368 (5)	N1—N2	1.361 (4)
C15—C20	1.369 (5)	N3—N4	1.383 (4)
C15—N6	1.440 (4)	N4—H4	0.8600
C16—C17	1.387 (5)	N5—N6	1.356 (4)
C16—H16	0.9300	N7—H7A	0.8600
C17—C18	1.351 (6)

C2—C1—H1A	109.5	C15—C20—H20	120.6
C2—C1—H1B	109.5	C19—C20—H20	120.6
H1A—C1—H1B	109.5	C22—C21—C23	105.9 (3)
C2—C1—H1C	109.5	C22—C21—C14	127.8 (3)
H1A—C1—H1C	109.5	C23—C21—C14	126.2 (3)
H1B—C1—H1C	109.5	N7—C22—C21	110.7 (3)
O1—C2—C3	117.9 (3)	N7—C22—H22	124.6
O1—C2—C1	123.1 (4)	C21—C22—H22	124.6
C3—C2—C1	119.0 (4)	C28—C23—C24	117.9 (3)
N1—C3—C2	124.5 (3)	C28—C23—C21	135.9 (3)
N1—C3—S1	116.5 (3)	C24—C23—C21	106.2 (3)
C2—C3—S1	119.0 (3)	N7—C24—C25	129.8 (3)
N3—C4—N2	123.3 (3)	N7—C24—C23	107.9 (3)
N3—C4—S1	128.3 (2)	C25—C24—C23	122.3 (3)
N2—C4—S1	108.4 (2)	C26—C25—C24	118.4 (4)
C10—C5—C6	120.6 (3)	C26—C25—H25	120.8
C10—C5—N2	118.8 (3)	C24—C25—H25	120.8
C6—C5—N2	120.6 (3)	C25—C26—C27	120.1 (4)
C5—C6—C7	119.5 (3)	C25—C26—H26	120.0
C5—C6—H6	120.2	C27—C26—H26	120.0
C7—C6—H6	120.2	C28—C27—C26	121.8 (4)
C8—C7—C6	119.7 (4)	C28—C27—H27	119.1
C8—C7—H7	120.1	C26—C27—H27	119.1
C6—C7—H7	120.1	C27—C28—C23	119.5 (3)
C7—C8—C9	120.5 (4)	C27—C28—H28	120.2
C7—C8—Cl1	120.1 (3)	C23—C28—H28	120.2
C9—C8—Cl1	119.4 (3)	N8—C29—H29A	109.5
C8—C9—C10	119.9 (4)	N8—C29—H29B	109.5
C8—C9—H9	120.0	H29A—C29—H29B	109.5
C10—C9—H9	120.0	N8—C29—H29C	109.5
C5—C10—C9	119.6 (4)	H29A—C29—H29C	109.5
C5—C10—H10	120.2	H29B—C29—H29C	109.5
C9—C10—H10	120.2	N8—C30—H30A	109.5
O2—C11—N4	124.0 (3)	N8—C30—H30B	109.5
O2—C11—C12	122.0 (3)	H30A—C30—H30B	109.5
N4—C11—C12	114.0 (3)	N8—C30—H30C	109.5
N5—C12—C13	112.0 (3)	H30A—C30—H30C	109.5
N5—C12—C11	120.3 (3)	H30B—C30—H30C	109.5
C13—C12—C11	127.8 (3)	O3—C31—N8	125.6 (4)
C14—C13—C12	106.2 (3)	O3—C31—H31	117.2
C14—C13—H13	126.9	N8—C31—H31	117.2
C12—C13—H13	126.9	C3—N1—N2	111.2 (3)
N6—C14—C13	105.0 (2)	N1—N2—C4	115.6 (3)
N6—C14—C21	125.7 (3)	N1—N2—C5	118.2 (2)
C13—C14—C21	129.3 (3)	C4—N2—C5	126.1 (3)
C16—C15—C20	121.5 (3)	C4—N3—N4	114.0 (3)
C16—C15—N6	118.7 (3)	C11—N4—N3	121.1 (3)
C20—C15—N6	119.8 (3)	C11—N4—H4	119.4
C15—C16—C17	118.7 (4)	N3—N4—H4	119.4
C15—C16—H16	120.7	C12—N5—N6	104.2 (2)
C17—C16—H16	120.7	N5—N6—C14	112.6 (2)
C18—C17—C16	120.9 (4)	N5—N6—C15	118.0 (2)
C18—C17—H17	119.5	C14—N6—C15	129.2 (2)
C16—C17—H17	119.5	C22—N7—C24	109.3 (3)
C17—C18—C19	120.0 (3)	C22—N7—H7A	125.3
C17—C18—H18	120.0	C24—N7—H7A	125.3
C19—C18—H18	120.0	C31—N8—C30	119.7 (3)
C18—C19—C20	120.1 (4)	C31—N8—C29	121.4 (4)
C18—C19—H19	119.9	C30—N8—C29	118.9 (3)
C20—C19—H19	119.9	C3—S1—C4	88.20 (16)
C15—C20—C19	118.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7A···O3	0.86	1.96	2.784 (4)	159
C16—H16···O2ⁱ	0.93	2.34	3.258 (5)	168

Symmetry code: (i) −x, −y+1, z−1/2.

Footnotes

‡Additional corresponding author, e-mail: kariukib@cardiff.ac.uk.

Acknowledgements

Mohammad Hayal Alotaibi thanks King Abdulaziz City for Science and Technology (KACST), Saudi Arabia for financial support (award No. 020–0180).

Funding information

MHA thanks King Abdulaziz City for Science and Technology (KACST), Saudi Arabia, for financial support (award No. 020–0180).

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