5-[(4-Bromo­phen­yl)diazen­yl]-2-{2-[1-(1H-indol-3-yl)ethyl­idene]hydrazin­yl}-4-methyl­thia­zole di­methyl­formamide hemisolvate

The asymmetric unit of the title compound, 2C₂₀H₁₇BrN₆S·C₃H₇NO, comprises two mol­ecules of the thia­zole derivative and one mol­ecule of di­methyl­formamide (DMF) solvent. The twist angles between the planes through the bromo­phenyl, methyl­thiazolyl and indolyl groups are 10.1 (1) and 44.2 (1)°, respectively, for one mol­ecule and 11.3 (1) and 1.6 (1)° for the other. In the crystal, N—H...N hydrogen bonds link four of the main mol­ecules into tetramers. N—H...O bonds involving the DMF solvent mol­ecule also occur.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.056
• wR factor = 0.145
• Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        48% Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C21 Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        N13 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        O1      0.104 Check
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
              C20 H17 Br N6 S
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -4.006 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.005 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C42 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600       1788 Note
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           2 Units
PLAT951_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ           2 Units
PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ           2 Units
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           2 Units
PLAT957_ALERT_1_G Calculated (ThMax) and Actual (FCF) Kmax Differ           2 Units
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ           2 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   4 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

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: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: ORTEP-3 for Windows and WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).

5-[(4-Bromophenyl)diazenyl]-2-{2-[1-(1H-indol-3-yl)ethylidene]hydrazinyl}-4-methylthiazole dimethylformamide hemisolvate

Crystal data

2C20H17BrN6S·C3H7NO	Z = 2
Mr = 979.83	F(000) = 1000
Triclinic, P1	Dx = 1.462 Mg m^−3
a = 9.9957 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.5325 (9) Å	Cell parameters from 3549 reflections
c = 15.8353 (10) Å	θ = 3.3–24.0°
α = 81.671 (5)°	µ = 1.97 mm^−1
β = 81.344 (5)°	T = 293 K
γ = 80.469 (5)°	Needle, colourless
V = 2225.7 (2) Å^3	0.25 × 0.09 × 0.04 mm

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	5116 reflections with I > 2σ(I)
ω scans	Rint = 0.036
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θmax = 29.9°, θmin = 1.3°
Tmin = 0.827, Tmax = 1.000	h = −12→12
19885 measured reflections	k = −18→17
10602 independent reflections	l = −20→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0515P)^2 + 0.5647P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
10602 reflections	Δρmax = 0.49 e Å^−3
556 parameters	Δρmin = −0.57 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3683 (4)	0.4890 (3)	0.2966 (3)	0.0661 (11)
C2	0.3605 (4)	0.5387 (3)	0.2167 (3)	0.0725 (12)
H2	0.439015	0.542822	0.177384	0.087*
C3	0.2340 (4)	0.5828 (3)	0.1951 (3)	0.0690 (12)
H3	0.227696	0.616794	0.141065	0.083*
C4	0.1170 (3)	0.5764 (3)	0.2536 (2)	0.0553 (10)
C5	0.1270 (4)	0.5278 (3)	0.3346 (2)	0.0686 (12)
H5	0.049302	0.524021	0.374718	0.082*
C6	0.2539 (4)	0.4849 (3)	0.3554 (3)	0.0755 (13)
H6	0.261508	0.452795	0.410069	0.091*
C7	−0.2388 (3)	0.6543 (3)	0.2642 (2)	0.0503 (9)
C8	−0.3603 (3)	0.6609 (3)	0.3284 (2)	0.0500 (9)
C9	−0.3516 (4)	0.6225 (3)	0.4198 (2)	0.0662 (11)
H9A	−0.296376	0.657467	0.443928	0.099*
H9B	−0.310921	0.557619	0.423143	0.099*
H9C	−0.441742	0.627509	0.451411	0.099*
C10	−0.4547 (3)	0.7334 (3)	0.2135 (2)	0.0503 (9)
C11	−0.7037 (4)	0.9302 (3)	0.0909 (3)	0.0775 (13)
H11A	−0.787420	0.911240	0.081728	0.116*
H11B	−0.702207	0.994822	0.067657	0.116*
H11C	−0.697737	0.922945	0.151532	0.116*
C12	−0.5837 (3)	0.8696 (3)	0.0466 (2)	0.0532 (9)
C13	−0.5446 (3)	0.8901 (3)	−0.0446 (2)	0.0527 (9)
C14	−0.5892 (4)	0.9712 (3)	−0.0958 (2)	0.0653 (11)
H14	−0.649707	1.021779	−0.076243	0.078*
C15	−0.4560 (3)	0.8309 (3)	−0.1020 (2)	0.0529 (9)
C16	−0.4509 (4)	0.8814 (3)	−0.1848 (2)	0.0582 (10)
C17	−0.3895 (4)	0.7384 (3)	−0.0925 (3)	0.0678 (11)
H17	−0.389359	0.703829	−0.038236	0.081*
C18	−0.3240 (4)	0.6987 (3)	−0.1647 (3)	0.0839 (14)
H18	−0.281517	0.636563	−0.159192	0.101*
C19	−0.3210 (4)	0.7514 (4)	−0.2458 (3)	0.0817 (14)
H19	−0.275533	0.723225	−0.293336	0.098*
C20	−0.3824 (4)	0.8428 (4)	−0.2583 (3)	0.0717 (12)
H20	−0.378876	0.877400	−0.312612	0.086*
C21	0.0369 (4)	0.8433 (3)	0.8874 (2)	0.0685 (12)
C22	0.1724 (4)	0.8075 (3)	0.8889 (3)	0.0677 (11)
H22	0.205456	0.785496	0.941102	0.081*
C23	0.2595 (4)	0.8043 (3)	0.8127 (2)	0.0627 (11)
H23	0.351116	0.778949	0.813263	0.075*
C24	0.2104 (4)	0.8386 (3)	0.7357 (2)	0.0562 (10)
C25	0.0725 (4)	0.8708 (3)	0.7344 (3)	0.0693 (12)
H25	0.038463	0.891244	0.682330	0.083*
C26	−0.0152 (4)	0.8725 (3)	0.8116 (3)	0.0752 (13)
H26	−0.108272	0.893379	0.811442	0.090*
C27	0.3534 (3)	0.8933 (3)	0.5193 (2)	0.0514 (9)
C28	0.3153 (3)	0.9414 (3)	0.4369 (2)	0.0540 (9)
C29	0.1725 (4)	0.9861 (3)	0.4279 (3)	0.0703 (12)
H29A	0.147110	1.035898	0.463550	0.105*
H29B	0.111992	0.939995	0.445346	0.105*
H29C	0.166113	1.011312	0.368891	0.105*
C30	0.5383 (3)	0.9026 (3)	0.3979 (2)	0.0514 (9)
C31	0.8812 (4)	0.8946 (3)	0.2322 (2)	0.0685 (12)
H31A	0.843492	0.855589	0.200746	0.103*
H31B	0.974539	0.898512	0.208218	0.103*
H31C	0.829083	0.956467	0.228339	0.103*
C32	0.8760 (4)	0.8529 (3)	0.3249 (2)	0.0523 (9)
C33	1.0005 (3)	0.8060 (3)	0.3569 (2)	0.0526 (9)
C34	1.1291 (4)	0.7972 (3)	0.3090 (2)	0.0624 (11)
H34	1.147138	0.821149	0.251346	0.075*
C35	1.0228 (3)	0.7596 (3)	0.4419 (2)	0.0507 (9)
C36	1.1629 (3)	0.7248 (3)	0.4387 (2)	0.0571 (10)
C37	0.9387 (4)	0.7430 (3)	0.5204 (2)	0.0646 (11)
H37	0.845420	0.765264	0.525577	0.077*
C38	0.9978 (4)	0.6929 (3)	0.5895 (3)	0.0821 (15)
H38	0.943053	0.681269	0.641737	0.099*
C39	1.1368 (4)	0.6592 (4)	0.5834 (3)	0.0864 (15)
H39	1.172934	0.625797	0.631515	0.104*
C40	1.2216 (4)	0.6739 (3)	0.5084 (3)	0.0726 (12)
H40	1.314643	0.650980	0.504184	0.087*
C41	0.0191 (5)	0.6113 (3)	−0.0223 (3)	0.0853 (14)
H41	−0.068023	0.636238	−0.035812	0.102*
C42	0.0817 (7)	0.5992 (4)	−0.1745 (3)	0.119 (2)
H42A	−0.012251	0.626721	−0.175802	0.178*
H42B	0.096583	0.539015	−0.195353	0.178*
H42C	0.139772	0.639613	−0.210323	0.178*
C43	0.2499 (6)	0.5465 (4)	−0.0693 (4)	0.127 (2)
H43A	0.311572	0.591228	−0.090221	0.191*
H43B	0.278569	0.491202	−0.097807	0.191*
H43C	0.250381	0.529812	−0.008373	0.191*
N1	−0.0093 (3)	0.6186 (2)	0.22832 (19)	0.0587 (8)
H1	−0.015244	0.643112	0.175984	0.070*
N2	−0.1210 (3)	0.6202 (2)	0.28697 (18)	0.0538 (8)
N3	−0.4736 (3)	0.7028 (2)	0.30121 (17)	0.0531 (8)
N4	−0.5533 (3)	0.7801 (2)	0.17471 (18)	0.0578 (8)
N5	−0.5105 (3)	0.7997 (2)	0.08630 (18)	0.0556 (8)
N6	−0.5323 (3)	0.9668 (2)	−0.1789 (2)	0.0667 (9)
H6A	−0.545184	1.010379	−0.220975	0.080*
N7	0.3037 (3)	0.8407 (2)	0.66017 (18)	0.0615 (9)
H7	0.386501	0.813022	0.661312	0.074*
N8	0.2636 (3)	0.8859 (2)	0.58613 (19)	0.0547 (8)
N9	0.4131 (3)	0.9447 (2)	0.37360 (18)	0.0552 (8)
N10	0.6473 (3)	0.9013 (2)	0.34273 (18)	0.0553 (8)
N11	0.7640 (3)	0.8559 (2)	0.37912 (17)	0.0543 (8)
N12	1.2240 (3)	0.7495 (2)	0.3570 (2)	0.0676 (9)
H12	1.309808	0.736557	0.339169	0.081*
N13	0.1136 (4)	0.5873 (3)	−0.0864 (2)	0.0866 (12)
O1	0.0371 (4)	0.6034 (3)	0.0529 (2)	0.1044 (12)
S1	−0.28472 (9)	0.70423 (7)	0.16186 (5)	0.0551 (3)
S2	0.53169 (9)	0.85338 (7)	0.50777 (6)	0.0563 (3)
Br1	0.53923 (5)	0.42261 (4)	0.32500 (4)	0.0973 (2)
Br2	−0.07975 (6)	0.84842 (4)	0.99418 (3)	0.1142 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.044 (2)	0.079 (3)	0.075 (3)	0.004 (2)	−0.0138 (19)	−0.018 (2)
C2	0.046 (2)	0.094 (3)	0.073 (3)	−0.002 (2)	−0.0002 (19)	−0.013 (2)
C3	0.048 (2)	0.089 (3)	0.061 (2)	0.000 (2)	−0.0017 (18)	0.003 (2)
C4	0.043 (2)	0.066 (3)	0.054 (2)	0.0027 (18)	−0.0023 (16)	−0.0114 (18)
C5	0.049 (2)	0.098 (3)	0.053 (2)	0.001 (2)	−0.0032 (17)	−0.005 (2)
C6	0.062 (3)	0.095 (3)	0.065 (3)	0.002 (2)	−0.016 (2)	−0.002 (2)
C7	0.045 (2)	0.057 (2)	0.045 (2)	0.0013 (17)	−0.0023 (15)	−0.0073 (16)
C8	0.046 (2)	0.055 (2)	0.042 (2)	0.0010 (17)	0.0028 (15)	−0.0020 (16)
C9	0.062 (2)	0.085 (3)	0.042 (2)	0.007 (2)	−0.0015 (17)	−0.0022 (19)
C10	0.0437 (19)	0.058 (2)	0.044 (2)	−0.0044 (17)	0.0026 (15)	−0.0010 (16)
C11	0.063 (3)	0.092 (3)	0.060 (3)	0.015 (2)	0.0027 (19)	0.006 (2)
C12	0.046 (2)	0.063 (3)	0.048 (2)	−0.0009 (18)	−0.0086 (16)	−0.0009 (18)
C13	0.050 (2)	0.062 (3)	0.042 (2)	−0.0020 (18)	−0.0095 (15)	0.0040 (17)
C14	0.071 (3)	0.070 (3)	0.049 (2)	0.002 (2)	−0.0030 (19)	−0.0037 (19)
C15	0.0446 (19)	0.064 (3)	0.048 (2)	−0.0047 (18)	−0.0088 (15)	−0.0014 (18)
C16	0.051 (2)	0.076 (3)	0.048 (2)	−0.010 (2)	−0.0048 (17)	−0.0084 (19)
C17	0.062 (2)	0.074 (3)	0.064 (3)	0.000 (2)	−0.006 (2)	−0.009 (2)
C18	0.075 (3)	0.084 (3)	0.087 (4)	0.008 (3)	−0.002 (2)	−0.023 (3)
C19	0.064 (3)	0.111 (4)	0.069 (3)	−0.010 (3)	0.010 (2)	−0.033 (3)
C20	0.061 (2)	0.102 (4)	0.053 (3)	−0.019 (3)	−0.0021 (19)	−0.012 (2)
C21	0.075 (3)	0.067 (3)	0.052 (2)	−0.004 (2)	0.014 (2)	−0.003 (2)
C22	0.073 (3)	0.078 (3)	0.052 (2)	−0.018 (2)	−0.006 (2)	−0.004 (2)
C23	0.048 (2)	0.085 (3)	0.054 (2)	−0.017 (2)	−0.0049 (17)	0.000 (2)
C24	0.050 (2)	0.067 (3)	0.048 (2)	−0.0084 (19)	0.0041 (16)	−0.0063 (18)
C25	0.055 (2)	0.084 (3)	0.058 (2)	0.007 (2)	−0.0014 (18)	0.001 (2)
C26	0.055 (2)	0.088 (3)	0.066 (3)	0.008 (2)	0.010 (2)	0.002 (2)
C27	0.0433 (19)	0.059 (2)	0.049 (2)	−0.0037 (17)	0.0014 (15)	−0.0069 (17)
C28	0.045 (2)	0.062 (3)	0.054 (2)	−0.0048 (18)	−0.0076 (17)	−0.0051 (18)
C29	0.047 (2)	0.085 (3)	0.072 (3)	0.000 (2)	−0.0087 (19)	0.003 (2)
C30	0.047 (2)	0.061 (2)	0.042 (2)	−0.0024 (18)	−0.0027 (15)	−0.0036 (17)
C31	0.059 (2)	0.091 (3)	0.050 (2)	−0.012 (2)	0.0064 (17)	−0.002 (2)
C32	0.050 (2)	0.056 (2)	0.048 (2)	−0.0083 (17)	0.0035 (16)	−0.0056 (17)
C33	0.0415 (19)	0.063 (3)	0.051 (2)	−0.0071 (17)	0.0041 (15)	−0.0095 (18)
C34	0.050 (2)	0.077 (3)	0.054 (2)	−0.007 (2)	0.0087 (18)	−0.007 (2)
C35	0.0411 (19)	0.062 (2)	0.048 (2)	−0.0073 (17)	0.0018 (15)	−0.0093 (17)
C36	0.042 (2)	0.070 (3)	0.056 (2)	−0.0045 (18)	0.0043 (17)	−0.0122 (19)
C37	0.044 (2)	0.088 (3)	0.055 (2)	0.002 (2)	0.0014 (17)	−0.005 (2)
C38	0.054 (2)	0.127 (4)	0.053 (3)	0.002 (3)	0.0039 (19)	0.002 (2)
C39	0.057 (3)	0.122 (4)	0.070 (3)	0.008 (3)	−0.013 (2)	0.004 (3)
C40	0.046 (2)	0.094 (3)	0.072 (3)	0.007 (2)	−0.007 (2)	−0.012 (2)
C41	0.099 (4)	0.082 (3)	0.069 (3)	−0.011 (3)	0.001 (3)	−0.005 (3)
C42	0.177 (6)	0.129 (5)	0.061 (3)	−0.060 (4)	−0.002 (3)	−0.019 (3)
C43	0.117 (5)	0.124 (5)	0.121 (5)	0.018 (4)	0.016 (4)	−0.023 (4)
N1	0.0427 (17)	0.076 (2)	0.0501 (18)	0.0044 (15)	−0.0012 (13)	−0.0040 (15)
N2	0.0424 (17)	0.063 (2)	0.0523 (18)	0.0013 (15)	−0.0014 (13)	−0.0090 (14)
N3	0.0461 (17)	0.064 (2)	0.0405 (17)	0.0002 (15)	0.0037 (12)	0.0017 (14)
N4	0.0459 (17)	0.072 (2)	0.0462 (18)	0.0031 (16)	−0.0017 (13)	0.0045 (15)
N5	0.0464 (16)	0.069 (2)	0.0433 (17)	0.0012 (15)	−0.0023 (13)	0.0034 (14)
N6	0.078 (2)	0.067 (2)	0.048 (2)	−0.0081 (19)	−0.0084 (16)	0.0102 (15)
N7	0.0465 (17)	0.082 (2)	0.0475 (19)	−0.0003 (16)	0.0031 (13)	−0.0008 (16)
N8	0.0475 (17)	0.064 (2)	0.0500 (19)	−0.0058 (15)	0.0004 (14)	−0.0064 (15)
N9	0.0444 (17)	0.070 (2)	0.0475 (18)	−0.0042 (15)	−0.0061 (13)	0.0009 (15)
N10	0.0461 (17)	0.071 (2)	0.0439 (17)	−0.0053 (15)	−0.0013 (13)	0.0015 (14)
N11	0.0433 (16)	0.072 (2)	0.0419 (16)	−0.0020 (15)	0.0003 (13)	−0.0008 (14)
N12	0.0408 (17)	0.088 (3)	0.065 (2)	−0.0022 (17)	0.0134 (15)	−0.0103 (18)
N13	0.105 (3)	0.092 (3)	0.060 (2)	−0.019 (2)	0.004 (2)	−0.011 (2)
O1	0.112 (3)	0.133 (3)	0.055 (2)	0.007 (2)	−0.0013 (17)	−0.0048 (19)
S1	0.0430 (5)	0.0724 (7)	0.0417 (5)	0.0009 (4)	0.0030 (4)	0.0005 (4)
S2	0.0450 (5)	0.0737 (7)	0.0425 (5)	0.0020 (5)	−0.0005 (4)	0.0007 (4)
Br1	0.0541 (3)	0.1219 (5)	0.1132 (4)	0.0158 (3)	−0.0292 (3)	−0.0197 (3)
Br2	0.1249 (5)	0.1113 (5)	0.0695 (3)	0.0243 (4)	0.0413 (3)	0.0070 (3)

Geometric parameters (Å, º)

C1—C6	1.365 (6)	C25—H25	0.9300
C1—C2	1.369 (6)	C26—H26	0.9300
C1—Br1	1.901 (3)	C27—N8	1.284 (4)
C2—C3	1.387 (5)	C27—C28	1.461 (5)
C2—H2	0.9300	C27—S2	1.771 (3)
C3—C4	1.384 (5)	C28—N9	1.292 (4)
C3—H3	0.9300	C28—C29	1.485 (5)
C4—C5	1.382 (5)	C29—H29A	0.9600
C4—N1	1.398 (4)	C29—H29B	0.9600
C5—C6	1.382 (5)	C29—H29C	0.9600
C5—H5	0.9300	C30—N10	1.290 (4)
C6—H6	0.9300	C30—N9	1.382 (4)
C7—N2	1.283 (4)	C30—S2	1.778 (3)
C7—C8	1.461 (4)	C31—C32	1.501 (5)
C7—S1	1.771 (3)	C31—H31A	0.9600
C8—N3	1.297 (4)	C31—H31B	0.9600
C8—C9	1.484 (5)	C31—H31C	0.9600
C9—H9A	0.9600	C32—N11	1.303 (4)
C9—H9B	0.9600	C32—C33	1.443 (5)
C9—H9C	0.9600	C33—C34	1.387 (5)
C10—N4	1.284 (4)	C33—C35	1.447 (5)
C10—N3	1.390 (4)	C34—N12	1.344 (5)
C10—S1	1.783 (3)	C34—H34	0.9300
C11—C12	1.510 (5)	C35—C36	1.404 (5)
C11—H11A	0.9600	C35—C37	1.406 (5)
C11—H11B	0.9600	C36—N12	1.370 (5)
C11—H11C	0.9600	C36—C40	1.388 (5)
C12—N5	1.292 (4)	C37—C38	1.378 (5)
C12—C13	1.441 (5)	C37—H37	0.9300
C13—C14	1.379 (5)	C38—C39	1.389 (5)
C13—C15	1.442 (5)	C38—H38	0.9300
C14—N6	1.358 (5)	C39—C40	1.363 (6)
C14—H14	0.9300	C39—H39	0.9300
C15—C17	1.396 (5)	C40—H40	0.9300
C15—C16	1.405 (5)	C41—O1	1.217 (5)
C16—N6	1.373 (5)	C41—N13	1.321 (6)
C16—C20	1.400 (5)	C41—H41	0.9300
C17—C18	1.382 (6)	C42—N13	1.458 (6)
C17—H17	0.9300	C42—H42A	0.9600
C18—C19	1.397 (6)	C42—H42B	0.9600
C18—H18	0.9300	C42—H42C	0.9600
C19—C20	1.367 (6)	C43—N13	1.442 (6)
C19—H19	0.9300	C43—H43A	0.9600
C20—H20	0.9300	C43—H43B	0.9600
C21—C26	1.363 (6)	C43—H43C	0.9600
C21—C22	1.370 (6)	N1—N2	1.340 (4)
C21—Br2	1.908 (4)	N1—H1	0.8600
C22—C23	1.380 (5)	N4—N5	1.403 (4)
C22—H22	0.9300	N6—H6A	0.8600
C23—C24	1.378 (5)	N7—N8	1.341 (4)
C23—H23	0.9300	N7—H7	0.8600
C24—C25	1.382 (5)	N10—N11	1.401 (4)
C24—N7	1.401 (4)	N12—H12	0.8600
C25—C26	1.394 (5)
C6—C1—C2	120.7 (3)	C28—C27—S2	109.2 (2)
C6—C1—Br1	119.6 (3)	N9—C28—C27	116.2 (3)
C2—C1—Br1	119.7 (3)	N9—C28—C29	122.4 (3)
C1—C2—C3	119.1 (4)	C27—C28—C29	121.3 (3)
C1—C2—H2	120.4	C28—C29—H29A	109.5
C3—C2—H2	120.4	C28—C29—H29B	109.5
C4—C3—C2	120.4 (4)	H29A—C29—H29B	109.5
C4—C3—H3	119.8	C28—C29—H29C	109.5
C2—C3—H3	119.8	H29A—C29—H29C	109.5
C5—C4—C3	119.7 (3)	H29B—C29—H29C	109.5
C5—C4—N1	121.5 (3)	N10—C30—N9	120.3 (3)
C3—C4—N1	118.8 (3)	N10—C30—S2	125.4 (3)
C4—C5—C6	119.1 (4)	N9—C30—S2	114.4 (2)
C4—C5—H5	120.4	C32—C31—H31A	109.5
C6—C5—H5	120.4	C32—C31—H31B	109.5
C1—C6—C5	120.8 (4)	H31A—C31—H31B	109.5
C1—C6—H6	119.6	C32—C31—H31C	109.5
C5—C6—H6	119.6	H31A—C31—H31C	109.5
N2—C7—C8	120.3 (3)	H31B—C31—H31C	109.5
N2—C7—S1	130.1 (3)	N11—C32—C33	117.2 (3)
C8—C7—S1	109.5 (2)	N11—C32—C31	123.7 (3)
N3—C8—C7	116.5 (3)	C33—C32—C31	119.1 (3)
N3—C8—C9	122.6 (3)	C34—C33—C32	125.2 (3)
C7—C8—C9	120.8 (3)	C34—C33—C35	104.9 (3)
C8—C9—H9A	109.5	C32—C33—C35	130.0 (3)
C8—C9—H9B	109.5	N12—C34—C33	110.9 (3)
H9A—C9—H9B	109.5	N12—C34—H34	124.6
C8—C9—H9C	109.5	C33—C34—H34	124.6
H9A—C9—H9C	109.5	C36—C35—C37	117.9 (3)
H9B—C9—H9C	109.5	C36—C35—C33	107.1 (3)
N4—C10—N3	121.4 (3)	C37—C35—C33	135.0 (3)
N4—C10—S1	123.9 (3)	N12—C36—C40	128.8 (3)
N3—C10—S1	114.7 (2)	N12—C36—C35	107.7 (3)
C12—C11—H11A	109.5	C40—C36—C35	123.4 (3)
C12—C11—H11B	109.5	C38—C37—C35	118.4 (3)
H11A—C11—H11B	109.5	C38—C37—H37	120.8
C12—C11—H11C	109.5	C35—C37—H37	120.8
H11A—C11—H11C	109.5	C37—C38—C39	121.8 (4)
H11B—C11—H11C	109.5	C37—C38—H38	119.1
N5—C12—C13	116.7 (3)	C39—C38—H38	119.1
N5—C12—C11	123.7 (3)	C40—C39—C38	121.6 (4)
C13—C12—C11	119.6 (3)	C40—C39—H39	119.2
C14—C13—C12	126.1 (3)	C38—C39—H39	119.2
C14—C13—C15	105.7 (3)	C39—C40—C36	116.9 (3)
C12—C13—C15	128.2 (3)	C39—C40—H40	121.5
N6—C14—C13	110.4 (3)	C36—C40—H40	121.5
N6—C14—H14	124.8	O1—C41—N13	125.2 (5)
C13—C14—H14	124.8	O1—C41—H41	117.4
C17—C15—C16	118.6 (3)	N13—C41—H41	117.4
C17—C15—C13	134.2 (3)	N13—C42—H42A	109.5
C16—C15—C13	106.9 (3)	N13—C42—H42B	109.5
N6—C16—C20	129.0 (4)	H42A—C42—H42B	109.5
N6—C16—C15	107.9 (3)	N13—C42—H42C	109.5
C20—C16—C15	122.9 (4)	H42A—C42—H42C	109.5
C18—C17—C15	119.2 (4)	H42B—C42—H42C	109.5
C18—C17—H17	120.4	N13—C43—H43A	109.5
C15—C17—H17	120.4	N13—C43—H43B	109.5
C17—C18—C19	120.4 (4)	H43A—C43—H43B	109.5
C17—C18—H18	119.8	N13—C43—H43C	109.5
C19—C18—H18	119.8	H43A—C43—H43C	109.5
C20—C19—C18	122.6 (4)	H43B—C43—H43C	109.5
C20—C19—H19	118.7	N2—N1—C4	118.9 (3)
C18—C19—H19	118.7	N2—N1—H1	120.5
C19—C20—C16	116.3 (4)	C4—N1—H1	120.5
C19—C20—H20	121.8	C7—N2—N1	119.9 (3)
C16—C20—H20	121.8	C8—N3—C10	111.6 (3)
C26—C21—C22	121.3 (4)	C10—N4—N5	110.8 (3)
C26—C21—Br2	120.2 (3)	C12—N5—N4	115.3 (3)
C22—C21—Br2	118.4 (3)	C14—N6—C16	109.1 (3)
C21—C22—C23	119.6 (4)	C14—N6—H6A	125.5
C21—C22—H22	120.2	C16—N6—H6A	125.5
C23—C22—H22	120.2	N8—N7—C24	119.9 (3)
C24—C23—C22	119.9 (4)	N8—N7—H7	120.1
C24—C23—H23	120.1	C24—N7—H7	120.1
C22—C23—H23	120.1	C27—N8—N7	118.7 (3)
C23—C24—C25	120.0 (3)	C28—N9—C30	112.3 (3)
C23—C24—N7	118.3 (3)	C30—N10—N11	112.1 (3)
C25—C24—N7	121.7 (3)	C32—N11—N10	113.7 (3)
C24—C25—C26	119.7 (4)	C34—N12—C36	109.4 (3)
C24—C25—H25	120.2	C34—N12—H12	125.3
C26—C25—H25	120.2	C36—N12—H12	125.3
C21—C26—C25	119.3 (4)	C41—N13—C43	120.0 (4)
C21—C26—H26	120.4	C41—N13—C42	121.1 (5)
C25—C26—H26	120.4	C43—N13—C42	118.9 (4)
N8—C27—C28	121.0 (3)	C7—S1—C10	87.65 (16)
N8—C27—S2	129.7 (3)	C27—S2—C30	87.89 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.08	2.782 (4)	138
N6—H6A···N9^i	0.86	2.62	3.292 (4)	136
N6—H6A···N10^i	0.86	2.42	3.234 (4)	159
N12—H12···N3^ii	0.86	2.15	3.011 (4)	177

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