N′-[5-Acetyl-3-(4-bromo­phen­yl)-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/S2414314619002487

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 2| February 2019| x190248

https://doi.org/10.1107/S2414314619002487

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N′-[5-Acetyl-3-(4-bromophenyl)-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, Egypt, ^dDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad, 64021, Iraq, ^eCenter of Excellence in Integrated Nano-Systems, 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 K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 15 January 2019; accepted 17 February 2019; online 22 February 2019)

The main molecule of the title dimethylformamide monosolvate, C₂₈H₂₀BrN₇O₂S·C₃H₇NO, comprises bromophenyl (A), thiadiazolyl (B), pyrazolyl (C), phenyl (D) and indolyl (E) ring systems with twist angles between the planes through neigbouring rings A/B, B/C, C/D and C/E of 33.7 (1), 14.8 (1), 60.7 (2) and 20.9 (1)°, respectively. In the crystal, the molecules are related by c-glide symmetry to form columns parallel to [001] which are linked by intermolecular N—H⋯O, C—H⋯O and C—H⋯Br contacts.

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

CCDC reference: 1897679

Structure description

1H-Pyrazole-3-carbohydrazides have been used in the synthesis of anti-nociceptive, anti-inflammatory and antipyretic agents (Malvar et al., 2014 ). In addition, 1,3,4-thiadiazoles have different biological activities and can be used as anticancer, diuretic, antibacterial, antifungal, antitubercular and leishmanicidal agents (Dawood & Farghaly, 2017 ; Li et al., 2013 ; Lv et al., 2018 ; Serban et al., 2018 ).

In the main molecule of the title compound (Fig. 1), the angles between planes of the bromophenyl (A), thiadiazolyl (B), pyrazolyl (C), phenyl (D) and indolyl (E) rings A/B, B/C, C/D and C/E are 33.7 (1), 14.8 (1), 60.7 (2) and 20.9 (1)° respectively. The molecules are related by c-glide symmetry to form columns parallel to [001] which are linked by intermolecular N—H⋯O, C—H⋯O and C—H⋯Br contacts (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O3ⁱ	0.96	2.64	3.390 (7)	135
C16—H16⋯O2ⁱⁱ	0.93	2.33	3.243 (6)	167
C30—H30B⋯O2ⁱⁱⁱ	0.96	2.59	3.409 (7)	144
C30—H30C⋯Br1ⁱⁱ	0.96	3.09	3.851 (8)	137
N7—H7A⋯O3	0.86	1.96	2.778 (5)	158
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z]$ .

Figure 1
An ORTEP representation of the asymmetric unit showing 50% probability ellipsoids.

Figure 2
A segment of the crystal structure showing intermolecular contacts as dotted lines.

Synthesis and crystallization

The title compound was synthesized from a coupling reaction of potassium 2-(5-(1H-indol-3-yl)-1-phenyl-1H-pyrazole-3-carbonyl)hydrazinecarbodithioate and N′-(4-bromophenyl)-2-oxopropanehydrazonoyl chloride in boiling ethanol for 2 h. The solid obtained was collected by filtration, washed with ethanol, dried and recrystallized from dimethylformamide to give pale-yellow crystals, m.p. 207–209°C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₈H₂₀BrN₇O₂S·C₃H₇NO
M_r	671.57
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	22.5145 (11), 18.1416 (10), 7.5928 (4)
V (Å³)	3101.3 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.44
Crystal size (mm)	0.43 × 0.08 × 0.07

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	0.603, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	32233, 7649, 4668
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.698

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.117, 1.05
No. of reflections	7649
No. of parameters	400
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.47
Absolute structure	Flack x determined using 1670 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−0.010 (4)
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), WinGX (Farrugia, 2012 ) and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1897679

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002487/ff4029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002487/ff4029Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619002487/ff4029Isup3.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: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: WinGX (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

N'-[5-Acetyl-3-(4-bromophenyl)-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

C₂₈H₂₀BrN₇O₂S·C₃H₇NO	D_x = 1.438 Mg m⁻³
M_r = 671.57	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 7129 reflections
a = 22.5145 (11) Å	θ = 3.6–23.5°
b = 18.1416 (10) Å	µ = 1.44 mm⁻¹
c = 7.5928 (4) Å	T = 296 K
V = 3101.3 (3) Å³	Needle, yellow
Z = 4	0.43 × 0.08 × 0.07 mm
F(000) = 1376

Data collection top

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	4668 reflections with I > 2σ(I)
ω scans	R_int = 0.040
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 29.7°, θ_min = 2.9°
T_min = 0.603, T_max = 1.000	h = −30→29
32233 measured reflections	k = −25→23
7649 independent reflections	l = −9→8

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0478P)² + 0.5275P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.117	(Δ/σ)_max = 0.001
S = 1.05	Δρ_max = 0.24 e Å⁻³
7649 reflections	Δρ_min = −0.47 e Å⁻³
400 parameters	Absolute structure: Flack x determined using 1670 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.010 (4)

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. All hydrogen atoms were placed in calculated positions and refined using a riding model. Bond distances for sp² C—H and N—H H atoms were set to 0.93 Å and 0.83 Å respectively and their U(iso) set to 1.2 times the U_eq(C/N). Methyl C—H distances were set to 0.96 Å and their U(iso) to 1.5 times the U_eq(C).

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

	x	y	z	U_iso*/U_eq
C1	0.3897 (3)	0.4221 (3)	0.6408 (8)	0.0837 (16)
H1A	0.356302	0.444067	0.582081	0.126*
H1B	0.425815	0.440213	0.589650	0.126*
H1C	0.388585	0.434567	0.763603	0.126*
C2	0.3870 (2)	0.3406 (3)	0.6206 (7)	0.0667 (13)
C3	0.4422 (2)	0.2995 (2)	0.5881 (6)	0.0547 (10)
C4	0.51645 (19)	0.2049 (2)	0.5342 (5)	0.0500 (10)
C5	0.59448 (19)	0.3031 (2)	0.4890 (6)	0.0484 (9)
C6	0.64365 (19)	0.2629 (2)	0.5380 (6)	0.0541 (10)
H6	0.638893	0.219197	0.600438	0.065*
C7	0.7001 (2)	0.2871 (3)	0.4948 (6)	0.0577 (11)
H7	0.733372	0.260064	0.527992	0.069*
C8	0.7062 (2)	0.3522 (3)	0.4013 (6)	0.0602 (12)
C9	0.6574 (2)	0.3925 (3)	0.3560 (8)	0.0701 (14)
H9	0.662173	0.436579	0.295034	0.084*
C10	0.6013 (2)	0.3688 (3)	0.3995 (6)	0.0622 (12)
H10	0.568268	0.396719	0.368931	0.075*
C11	0.55267 (19)	0.0189 (2)	0.5084 (6)	0.0541 (10)
C12	0.51441 (18)	−0.0475 (2)	0.5128 (6)	0.0513 (10)
C13	0.53273 (19)	−0.1208 (2)	0.5265 (6)	0.0517 (10)
H13	0.571539	−0.137875	0.536277	0.062*
C14	0.48203 (17)	−0.1626 (2)	0.5226 (6)	0.0472 (9)
C15	0.37354 (17)	−0.1260 (2)	0.4977 (6)	0.0466 (9)
C16	0.34397 (19)	−0.1040 (2)	0.3485 (7)	0.0576 (11)
H16	0.363863	−0.078225	0.260606	0.069*
C17	0.2842 (2)	−0.1206 (3)	0.3301 (9)	0.0651 (11)
H17	0.263868	−0.105882	0.229427	0.078*
C18	0.2550 (2)	−0.1586 (3)	0.4596 (7)	0.0640 (12)
H18	0.215127	−0.170651	0.445588	0.077*
C19	0.28450 (19)	−0.1790 (3)	0.6101 (7)	0.0673 (13)
H19	0.264293	−0.203851	0.698854	0.081*
C20	0.3442 (2)	−0.1626 (3)	0.6306 (6)	0.0615 (12)
H20	0.364259	−0.176217	0.732770	0.074*
C21	0.47552 (17)	−0.2425 (2)	0.5177 (5)	0.0440 (9)
C22	0.4284 (2)	−0.2829 (2)	0.4545 (6)	0.0523 (10)
H22	0.393088	−0.262786	0.412896	0.063*
C23	0.52041 (18)	−0.2960 (2)	0.5668 (5)	0.0469 (9)
C24	0.49597 (19)	−0.3659 (2)	0.5303 (6)	0.0508 (10)
C25	0.5267 (2)	−0.4314 (3)	0.5657 (7)	0.0657 (13)
H25	0.509703	−0.477101	0.541998	0.079*
C26	0.5828 (2)	−0.4261 (3)	0.6366 (7)	0.0716 (14)
H26	0.604382	−0.468623	0.660842	0.086*
C27	0.6073 (2)	−0.3574 (3)	0.6719 (7)	0.0698 (14)
H27	0.645174	−0.354899	0.720389	0.084*
C28	0.5772 (2)	−0.2927 (3)	0.6375 (6)	0.0568 (11)
H28	0.594717	−0.247368	0.661414	0.068*
C29	0.2960 (2)	−0.4028 (3)	0.3714 (7)	0.0662 (14)
H29	0.299482	−0.353383	0.402596	0.079*
C30	0.1916 (2)	−0.3787 (3)	0.3324 (11)	0.0904 (17)
H30A	0.203331	−0.330110	0.368477	0.136*
H30B	0.163074	−0.397962	0.414266	0.136*
H30C	0.174254	−0.376465	0.217055	0.136*
C31	0.2340 (3)	−0.5018 (3)	0.2780 (10)	0.096 (2)
H31A	0.260659	−0.514233	0.183886	0.143*
H31B	0.193745	−0.508224	0.239159	0.143*
H31C	0.241467	−0.533296	0.377059	0.143*
N1	0.49317 (16)	0.32977 (19)	0.5631 (5)	0.0532 (9)
N2	0.53610 (15)	0.27826 (18)	0.5312 (5)	0.0492 (8)
N3	0.55051 (16)	0.15014 (19)	0.5048 (5)	0.0582 (9)
N4	0.52156 (17)	0.08241 (19)	0.5083 (6)	0.0643 (10)
H4	0.483382	0.081022	0.510462	0.077*
N5	0.45573 (15)	−0.04195 (19)	0.5049 (5)	0.0549 (9)
N6	0.43603 (15)	−0.11289 (17)	0.5122 (5)	0.0499 (8)
N7	0.44049 (16)	−0.35617 (19)	0.4611 (5)	0.0548 (9)
H7A	0.417057	−0.390819	0.427196	0.066*
N8	0.24315 (16)	−0.4262 (2)	0.3285 (6)	0.0628 (9)
O1	0.34070 (16)	0.3057 (2)	0.6310 (7)	0.0971 (13)
O2	0.60639 (14)	0.01563 (17)	0.5076 (5)	0.0746 (10)
O3	0.34165 (15)	−0.4403 (2)	0.3744 (5)	0.0779 (11)
S1	0.43969 (5)	0.20386 (6)	0.57886 (17)	0.0612 (3)
Br1	0.78288 (3)	0.38447 (4)	0.33102 (11)	0.0965 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.080 (4)	0.065 (3)	0.106 (4)	0.017 (3)	0.007 (3)	−0.008 (3)
C2	0.062 (3)	0.068 (3)	0.070 (3)	0.011 (3)	0.008 (2)	0.000 (2)
C3	0.056 (3)	0.052 (2)	0.056 (2)	0.000 (2)	−0.001 (2)	0.000 (2)
C4	0.053 (2)	0.044 (2)	0.053 (2)	−0.003 (2)	−0.002 (2)	0.0010 (19)
C5	0.050 (2)	0.043 (2)	0.052 (2)	−0.0047 (19)	0.0000 (19)	−0.0032 (18)
C6	0.053 (2)	0.048 (2)	0.062 (3)	−0.003 (2)	−0.002 (2)	0.0023 (19)
C7	0.053 (2)	0.059 (3)	0.062 (3)	−0.001 (2)	−0.002 (2)	−0.006 (2)
C8	0.059 (3)	0.062 (3)	0.060 (3)	−0.014 (2)	0.005 (2)	−0.003 (2)
C9	0.075 (3)	0.060 (3)	0.075 (3)	−0.014 (3)	−0.002 (3)	0.016 (2)
C10	0.062 (3)	0.052 (3)	0.073 (3)	−0.001 (2)	−0.003 (2)	0.012 (2)
C11	0.048 (2)	0.043 (2)	0.071 (3)	−0.0050 (19)	0.005 (2)	−0.013 (2)
C12	0.047 (2)	0.043 (2)	0.064 (2)	−0.0058 (18)	0.002 (2)	−0.0079 (19)
C13	0.039 (2)	0.047 (2)	0.070 (3)	−0.0007 (18)	0.003 (2)	−0.008 (2)
C14	0.039 (2)	0.046 (2)	0.057 (2)	0.0027 (18)	−0.0003 (19)	−0.0037 (19)
C15	0.040 (2)	0.042 (2)	0.058 (2)	0.0022 (17)	0.0017 (19)	−0.0025 (18)
C16	0.053 (2)	0.060 (3)	0.060 (3)	0.000 (2)	0.003 (2)	0.004 (2)
C17	0.050 (2)	0.081 (3)	0.065 (3)	0.003 (2)	−0.010 (2)	0.001 (3)
C18	0.043 (2)	0.071 (3)	0.078 (3)	−0.002 (2)	−0.002 (2)	−0.009 (3)
C19	0.044 (3)	0.075 (3)	0.083 (4)	−0.002 (2)	0.011 (2)	0.012 (3)
C20	0.050 (3)	0.069 (3)	0.066 (3)	0.003 (2)	0.002 (2)	0.012 (2)
C21	0.039 (2)	0.043 (2)	0.050 (2)	−0.0021 (17)	0.0006 (17)	−0.0002 (17)
C22	0.053 (3)	0.040 (2)	0.064 (3)	0.0024 (19)	−0.002 (2)	−0.0015 (19)
C23	0.045 (2)	0.048 (2)	0.048 (2)	0.0000 (18)	0.0043 (19)	0.0015 (19)
C24	0.048 (2)	0.047 (2)	0.058 (3)	0.0019 (19)	0.009 (2)	0.0057 (19)
C25	0.067 (3)	0.048 (2)	0.083 (3)	0.008 (2)	0.012 (3)	0.007 (2)
C26	0.069 (3)	0.064 (3)	0.082 (3)	0.022 (3)	0.011 (3)	0.011 (3)
C27	0.048 (3)	0.087 (4)	0.074 (3)	0.014 (3)	0.000 (2)	0.011 (3)
C28	0.047 (2)	0.063 (3)	0.060 (3)	0.000 (2)	0.002 (2)	0.000 (2)
C29	0.066 (3)	0.052 (3)	0.081 (4)	−0.010 (2)	0.000 (3)	−0.005 (2)
C30	0.060 (3)	0.106 (4)	0.105 (4)	0.026 (3)	0.008 (4)	0.008 (4)
C31	0.069 (3)	0.081 (4)	0.137 (6)	−0.013 (3)	−0.010 (4)	−0.021 (4)
N1	0.054 (2)	0.0465 (19)	0.060 (2)	0.0050 (17)	−0.0029 (18)	−0.0008 (17)
N2	0.051 (2)	0.0384 (17)	0.058 (2)	−0.0025 (16)	−0.0022 (17)	0.0003 (15)
N3	0.054 (2)	0.0400 (19)	0.081 (3)	−0.0071 (17)	0.0012 (19)	−0.0058 (18)
N4	0.047 (2)	0.0410 (19)	0.105 (3)	−0.0072 (17)	−0.001 (2)	−0.004 (2)
N5	0.0439 (19)	0.0415 (18)	0.079 (2)	−0.0070 (16)	0.0025 (18)	−0.0021 (17)
N6	0.0412 (19)	0.0385 (18)	0.070 (2)	−0.0014 (14)	−0.0009 (17)	0.0003 (16)
N7	0.048 (2)	0.043 (2)	0.074 (2)	−0.0066 (16)	0.0012 (18)	−0.0019 (17)
N8	0.050 (2)	0.061 (2)	0.077 (2)	0.0010 (18)	0.001 (2)	0.000 (2)
O1	0.056 (2)	0.092 (3)	0.143 (4)	−0.001 (2)	0.027 (2)	−0.005 (2)
O2	0.0462 (18)	0.0546 (18)	0.123 (3)	−0.0040 (15)	0.0031 (19)	−0.0244 (19)
O3	0.0514 (19)	0.066 (2)	0.116 (3)	0.0022 (17)	−0.0122 (19)	−0.0135 (19)
S1	0.0511 (6)	0.0541 (6)	0.0784 (7)	−0.0046 (5)	0.0081 (6)	0.0059 (6)
Br1	0.0713 (4)	0.1188 (5)	0.0994 (4)	−0.0342 (3)	0.0136 (4)	0.0080 (4)

Geometric parameters (Å, º) top

C1—C2	1.487 (7)	C17—H17	0.9300
C1—H1A	0.9600	C18—C19	1.372 (7)
C1—H1B	0.9600	C18—H18	0.9300
C1—H1C	0.9600	C19—C20	1.386 (6)
C2—O1	1.222 (6)	C19—H19	0.9300
C2—C3	1.471 (6)	C20—H20	0.9300
C3—N1	1.286 (5)	C21—C22	1.376 (6)
C3—S1	1.738 (4)	C21—C23	1.449 (6)
C4—N3	1.274 (5)	C22—N7	1.357 (5)
C4—N2	1.403 (5)	C22—H22	0.9300
C4—S1	1.761 (4)	C23—C28	1.387 (6)
C5—C6	1.377 (6)	C23—C24	1.410 (6)
C5—C10	1.380 (6)	C24—N7	1.367 (5)
C5—N2	1.426 (5)	C24—C25	1.402 (6)
C6—C7	1.384 (6)	C25—C26	1.377 (7)
C6—H6	0.9300	C25—H25	0.9300
C7—C8	1.385 (7)	C26—C27	1.389 (7)
C7—H7	0.9300	C26—H26	0.9300
C8—C9	1.364 (7)	C27—C28	1.381 (7)
C8—Br1	1.898 (5)	C27—H27	0.9300
C9—C10	1.375 (7)	C28—H28	0.9300
C9—H9	0.9300	C29—O3	1.234 (6)
C10—H10	0.9300	C29—N8	1.304 (6)
C11—O2	1.211 (5)	C29—H29	0.9300
C11—N4	1.348 (5)	C30—N8	1.446 (6)
C11—C12	1.482 (6)	C30—H30A	0.9600
C12—N5	1.326 (5)	C30—H30B	0.9600
C12—C13	1.397 (6)	C30—H30C	0.9600
C13—C14	1.370 (5)	C31—N8	1.438 (7)
C13—H13	0.9300	C31—H31A	0.9600
C14—N6	1.375 (5)	C31—H31B	0.9600
C14—C21	1.458 (5)	C31—H31C	0.9600
C15—C16	1.373 (6)	N1—N2	1.366 (5)
C15—C20	1.377 (6)	N3—N4	1.391 (5)
C15—N6	1.431 (5)	N4—H4	0.8600
C16—C17	1.386 (6)	N5—N6	1.362 (5)
C16—H16	0.9300	N7—H7A	0.8600
C17—C18	1.369 (8)

C2—C1—H1A	109.5	C15—C20—H20	120.5
C2—C1—H1B	109.5	C19—C20—H20	120.5
H1A—C1—H1B	109.5	C22—C21—C23	105.7 (3)
C2—C1—H1C	109.5	C22—C21—C14	128.0 (4)
H1A—C1—H1C	109.5	C23—C21—C14	126.1 (3)
H1B—C1—H1C	109.5	N7—C22—C21	110.7 (4)
O1—C2—C3	118.0 (4)	N7—C22—H22	124.6
O1—C2—C1	122.9 (5)	C21—C22—H22	124.6
C3—C2—C1	119.1 (5)	C28—C23—C24	118.3 (4)
N1—C3—C2	124.3 (4)	C28—C23—C21	135.5 (4)
N1—C3—S1	116.7 (3)	C24—C23—C21	106.2 (4)
C2—C3—S1	119.0 (4)	N7—C24—C25	129.3 (4)
N3—C4—N2	123.2 (4)	N7—C24—C23	108.4 (4)
N3—C4—S1	128.0 (3)	C25—C24—C23	122.2 (4)
N2—C4—S1	108.8 (3)	C26—C25—C24	117.9 (5)
C6—C5—C10	120.0 (4)	C26—C25—H25	121.0
C6—C5—N2	120.8 (4)	C24—C25—H25	121.0
C10—C5—N2	119.1 (4)	C25—C26—C27	120.2 (5)
C5—C6—C7	120.4 (4)	C25—C26—H26	119.9
C5—C6—H6	119.8	C27—C26—H26	119.9
C7—C6—H6	119.8	C28—C27—C26	122.1 (5)
C6—C7—C8	118.9 (4)	C28—C27—H27	119.0
C6—C7—H7	120.5	C26—C27—H27	119.0
C8—C7—H7	120.5	C27—C28—C23	119.3 (4)
C9—C8—C7	120.4 (4)	C27—C28—H28	120.4
C9—C8—Br1	119.7 (4)	C23—C28—H28	120.4
C7—C8—Br1	119.8 (4)	O3—C29—N8	125.7 (5)
C8—C9—C10	120.8 (5)	O3—C29—H29	117.1
C8—C9—H9	119.6	N8—C29—H29	117.1
C10—C9—H9	119.6	N8—C30—H30A	109.5
C9—C10—C5	119.4 (5)	N8—C30—H30B	109.5
C9—C10—H10	120.3	H30A—C30—H30B	109.5
C5—C10—H10	120.3	N8—C30—H30C	109.5
O2—C11—N4	124.1 (4)	H30A—C30—H30C	109.5
O2—C11—C12	122.7 (4)	H30B—C30—H30C	109.5
N4—C11—C12	113.1 (4)	N8—C31—H31A	109.5
N5—C12—C13	111.7 (4)	N8—C31—H31B	109.5
N5—C12—C11	121.1 (4)	H31A—C31—H31B	109.5
C13—C12—C11	127.2 (4)	N8—C31—H31C	109.5
C14—C13—C12	106.2 (4)	H31A—C31—H31C	109.5
C14—C13—H13	126.9	H31B—C31—H31C	109.5
C12—C13—H13	126.9	C3—N1—N2	111.4 (3)
C13—C14—N6	105.4 (3)	N1—N2—C4	115.0 (3)
C13—C14—C21	129.4 (4)	N1—N2—C5	118.4 (3)
N6—C14—C21	125.1 (3)	C4—N2—C5	126.5 (4)
C16—C15—C20	120.9 (4)	C4—N3—N4	113.8 (4)
C16—C15—N6	119.5 (4)	C11—N4—N3	120.7 (4)
C20—C15—N6	119.6 (4)	C11—N4—H4	119.6
C15—C16—C17	119.4 (5)	N3—N4—H4	119.6
C15—C16—H16	120.3	C12—N5—N6	104.5 (3)
C17—C16—H16	120.3	N5—N6—C14	112.1 (3)
C18—C17—C16	120.2 (5)	N5—N6—C15	118.3 (3)
C18—C17—H17	119.9	C14—N6—C15	129.5 (3)
C16—C17—H17	119.9	C22—N7—C24	108.9 (4)
C17—C18—C19	120.1 (4)	C22—N7—H7A	125.6
C17—C18—H18	120.0	C24—N7—H7A	125.6
C19—C18—H18	120.0	C29—N8—C31	120.6 (4)
C18—C19—C20	120.4 (4)	C29—N8—C30	122.1 (5)
C18—C19—H19	119.8	C31—N8—C30	117.3 (4)
C20—C19—H19	119.8	C3—S1—C4	88.0 (2)
C15—C20—C19	119.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O3ⁱ	0.96	2.64	3.390 (7)	135
C16—H16···O2ⁱⁱ	0.93	2.33	3.243 (6)	167
C30—H30B···O2ⁱⁱⁱ	0.96	2.59	3.409 (7)	144
C30—H30C···Br1ⁱⁱ	0.96	3.09	3.851 (8)	137
N7—H7A···O3	0.86	1.96	2.778 (5)	158

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

Footnotes

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

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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