S-Benzyl 3-(2-bromo­benzyl­idene)dithio­carbazate

The title compound, C₁₅H₁₃BrN₂S₂, crystallizes with two independent mol­ecules in the asymmetric unit. Both mol­ecules display a `C-shaped' conformation, with a trans configuration with respect to the C=N double bond. Inter­molecular N—H...S inter­actions are observed.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.044
• wR factor = 0.122
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         32 Perc.
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C25    -C30           1.36 Ang.

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.792
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.105
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C26
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C10    -C15           1.37 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

S1. Comment

As an extension of our work on the structural characterization of Schiff-base compounds (Qiu, Fang et al., 2006; Qiu, Luo et al., 2006), we report here the crystal structure of the title compound. The asymmetric unit consists of two independent molecules (Fig. 1), both of which display a "C-shaped" conformation. In both independent molecules, all bond lengths and angles lie within normal ranges: the C7=N1 and C22=N3 bond lengths of 1.272 (7) and 1.257 (7) Å conform to the expected value for a C=N double bond. The bond lengths of 1.324 (6) and 1.338 (7) Å for C8—N2 and C23—N4, respectively, lie between the expected values for a double and single bond, because of conjugation effects in the molecule. The dihedral angle between the two benzene rings in each molecule is 107.9 (6) and 105.1 (6) ° for the two independent molecules, respectively. In the crystal, intermolecular N—H···S interactions are observed.

Related literature

For related Schiff base structures, see: Qiu, Fang et al. (2006); Qiu, Luo, et al. (2006).

S2. Experimental

The title compound was synthesized by reaction of equivalent amounts of S-benzyldithiocarbazate (1 mmol, 0.20 g) and 2-bromobenzaldehyde (1 mmol, 0.19 g) in ethanol (20 ml) for 1 h at 373–383 K. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanol solution.

S3. Refinement

Atoms H2 and H4 were visible in a difference Fourier map, but were placed in calculated positions (N—H = 0.86 Å) and refined as riding with U_iso(H) = 1.2U_eq(N). All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H distances of 0.93 or 0.97 Å and with U_iso(H) = 1.2U_eq(C). The higher-angle diffraction data were weak, with only 1750 out of 5399 unique reflections observed (I > 2σ(I)) to θ_max = 25.0°, and the resulting structure is of relatively low precision.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures

Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at 30% for non-H atoms. Dashed lines denote N—H···S hydrogen bonds.

S-Benzyl 3-(2-bromobenzylidene)dithiocarbazate

Crystal data

C15H13BrN2S2	F(000) = 1472
Mr = 365.30	Dx = 1.540 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3876 reflections
a = 22.465 (6) Å	θ = 4.2–25°
b = 5.9323 (17) Å	µ = 2.86 mm^−1
c = 23.668 (7) Å	T = 298 K
β = 92.432 (5)°	Block, yellow
V = 3151.4 (16) Å^3	0.12 × 0.07 × 0.06 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer	5399 independent reflections
Radiation source: fine-focus sealed tube	1750 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.105
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→26
Tmin = 0.725, Tmax = 0.847	k = −6→6
17549 measured reflections	l = −28→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 0.79	w = 1/[σ^2(Fo^2) + (0.0502P)^2] where P = (Fo^2 + 2Fc^2)/3
5399 reflections	(Δ/σ)max = 0.001
361 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.38156 (4)	0.81077 (15)	1.06812 (3)	0.1124 (4)
Br2	0.43680 (3)	1.27449 (14)	0.61505 (4)	0.1031 (3)
C1	0.3175 (3)	0.7293 (14)	1.0175 (3)	0.077 (2)
C2	0.3203 (3)	0.5446 (11)	0.9824 (3)	0.0654 (18)
C3	0.2709 (3)	0.4962 (12)	0.9467 (3)	0.083 (2)
H3A	0.2711	0.3699	0.9234	0.099*
C4	0.2221 (3)	0.6354 (15)	0.9459 (3)	0.102 (3)
H4A	0.1900	0.6046	0.9210	0.123*
C5	0.2195 (4)	0.8175 (14)	0.9808 (3)	0.101 (3)
H5A	0.1856	0.9074	0.9811	0.122*
C6	0.2683 (4)	0.8640 (13)	1.0155 (3)	0.098 (2)
H6A	0.2679	0.9915	1.0383	0.117*
C7	0.3727 (3)	0.3955 (12)	0.9836 (3)	0.0703 (19)
H7A	0.4027	0.4135	1.0115	0.084*
C8	0.4342 (2)	−0.0640 (12)	0.9179 (2)	0.0659 (18)
C9	0.4007 (3)	−0.3370 (11)	0.8268 (3)	0.085 (2)
H9A	0.4418	−0.3170	0.8168	0.102*
H9B	0.3984	−0.4707	0.8502	0.102*
C10	0.3617 (3)	−0.3658 (12)	0.7741 (3)	0.0601 (17)
C11	0.3642 (3)	−0.2141 (12)	0.7310 (3)	0.082 (2)
H11A	0.3881	−0.0868	0.7353	0.098*
C12	0.3316 (4)	−0.2477 (14)	0.6813 (3)	0.101 (3)
H12A	0.3339	−0.1448	0.6518	0.121*
C13	0.2960 (3)	−0.4325 (18)	0.6755 (3)	0.100 (3)
H13A	0.2736	−0.4542	0.6420	0.120*
C14	0.2928 (3)	−0.5855 (13)	0.7178 (4)	0.091 (2)
H14A	0.2681	−0.7108	0.7134	0.110*
C15	0.3257 (3)	−0.5547 (12)	0.7667 (3)	0.075 (2)
H15A	0.3241	−0.6611	0.7955	0.090*
C16	0.4832 (3)	1.1731 (14)	0.6791 (3)	0.0723 (19)
C17	0.5172 (3)	0.9776 (13)	0.6768 (3)	0.075 (2)
C18	0.5487 (3)	0.9139 (13)	0.7264 (3)	0.095 (2)
H18A	0.5725	0.7855	0.7268	0.114*
C19	0.5445 (4)	1.0426 (17)	0.7755 (3)	0.109 (3)
H19A	0.5650	0.9970	0.8085	0.131*
C20	0.5111 (4)	1.2324 (16)	0.7760 (3)	0.106 (3)
H20A	0.5088	1.3171	0.8088	0.128*
C21	0.4808 (3)	1.2978 (12)	0.7275 (4)	0.092 (2)
H21A	0.4581	1.4291	0.7274	0.110*
C22	0.5213 (3)	0.8447 (12)	0.6253 (3)	0.071 (2)
H22A	0.4955	0.8756	0.5946	0.085*
C23	0.5898 (3)	0.3934 (12)	0.5621 (2)	0.0720 (19)
C24	0.6815 (3)	0.0966 (11)	0.5928 (2)	0.080 (2)
H24A	0.6555	−0.0333	0.5882	0.096*
H24B	0.6974	0.1321	0.5563	0.096*
C25	0.7320 (3)	0.0452 (14)	0.6356 (3)	0.075 (2)
C26	0.7806 (4)	0.1761 (14)	0.6396 (3)	0.127 (3)
H26A	0.7831	0.3018	0.6163	0.153*
C27	0.8270 (4)	0.1273 (18)	0.6777 (4)	0.144 (4)
H27A	0.8600	0.2217	0.6803	0.173*
C28	0.8248 (4)	−0.0578 (18)	0.7116 (3)	0.110 (3)
H28A	0.8560	−0.0904	0.7374	0.133*
C29	0.7776 (5)	−0.1902 (14)	0.7070 (3)	0.111 (3)
H29A	0.7761	−0.3192	0.7293	0.133*
C30	0.7304 (3)	−0.1405 (13)	0.6698 (3)	0.084 (2)
H30A	0.6972	−0.2341	0.6680	0.101*
N1	0.3769 (2)	0.2421 (10)	0.9464 (2)	0.0724 (15)
N2	0.4263 (2)	0.1106 (10)	0.9516 (2)	0.0770 (16)
H2	0.4532	0.1415	0.9774	0.092*
N3	0.5589 (2)	0.6892 (10)	0.6216 (2)	0.0774 (17)
N4	0.5567 (2)	0.5759 (10)	0.5714 (2)	0.0795 (17)
H4	0.5329	0.6239	0.5446	0.095*
S1	0.49163 (8)	−0.2385 (3)	0.92583 (7)	0.0950 (7)
S2	0.37642 (7)	−0.0936 (3)	0.86578 (7)	0.0773 (6)
S3	0.58178 (8)	0.2452 (3)	0.50331 (7)	0.0931 (6)
S4	0.64041 (7)	0.3345 (3)	0.61861 (7)	0.0773 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.1210 (7)	0.1233 (8)	0.0901 (6)	0.0066 (6)	−0.0297 (5)	−0.0369 (5)
Br2	0.0768 (5)	0.1047 (7)	0.1263 (7)	0.0116 (5)	−0.0130 (5)	0.0037 (5)
C1	0.080 (5)	0.100 (7)	0.052 (4)	0.017 (5)	0.001 (4)	−0.007 (4)
C2	0.084 (5)	0.058 (5)	0.053 (4)	0.017 (4)	−0.006 (4)	−0.004 (4)
C3	0.083 (5)	0.091 (6)	0.072 (5)	0.005 (5)	−0.016 (4)	−0.027 (4)
C4	0.079 (6)	0.107 (7)	0.118 (7)	0.039 (5)	−0.022 (5)	−0.008 (6)
C5	0.100 (7)	0.087 (7)	0.117 (7)	0.044 (5)	−0.002 (5)	−0.019 (5)
C6	0.112 (7)	0.096 (7)	0.083 (6)	0.020 (6)	−0.004 (5)	−0.027 (5)
C7	0.074 (5)	0.065 (5)	0.071 (5)	0.007 (4)	−0.014 (4)	0.004 (4)
C8	0.051 (4)	0.082 (5)	0.064 (4)	0.013 (4)	−0.013 (3)	−0.012 (4)
C9	0.074 (5)	0.084 (5)	0.095 (5)	0.026 (4)	−0.018 (4)	−0.022 (4)
C10	0.063 (4)	0.057 (5)	0.060 (5)	0.014 (4)	−0.004 (4)	−0.002 (4)
C11	0.092 (5)	0.080 (6)	0.073 (5)	−0.024 (4)	−0.009 (4)	0.005 (5)
C12	0.129 (7)	0.091 (7)	0.082 (6)	0.004 (6)	−0.005 (5)	0.018 (5)
C13	0.097 (7)	0.128 (9)	0.071 (6)	0.023 (6)	−0.031 (5)	−0.027 (6)
C14	0.067 (5)	0.077 (6)	0.127 (7)	−0.009 (4)	−0.023 (5)	−0.012 (6)
C15	0.084 (5)	0.057 (6)	0.084 (6)	−0.001 (4)	−0.001 (4)	0.013 (4)
C16	0.062 (5)	0.069 (6)	0.085 (6)	−0.019 (4)	0.001 (4)	−0.007 (5)
C17	0.078 (5)	0.065 (6)	0.082 (6)	−0.005 (4)	−0.002 (5)	−0.012 (5)
C18	0.103 (6)	0.090 (6)	0.091 (6)	0.022 (5)	−0.018 (5)	−0.011 (5)
C19	0.124 (7)	0.122 (8)	0.079 (6)	0.014 (6)	−0.023 (5)	−0.026 (6)
C20	0.109 (7)	0.116 (8)	0.093 (7)	0.023 (6)	−0.006 (5)	−0.030 (6)
C21	0.072 (5)	0.083 (6)	0.121 (7)	0.000 (4)	0.003 (5)	−0.010 (6)
C22	0.063 (5)	0.077 (6)	0.070 (5)	−0.008 (4)	−0.014 (4)	−0.003 (4)
C23	0.075 (5)	0.078 (6)	0.061 (4)	−0.012 (4)	−0.014 (4)	−0.009 (4)
C24	0.087 (5)	0.079 (5)	0.073 (5)	0.001 (4)	−0.008 (4)	−0.013 (4)
C25	0.080 (6)	0.071 (6)	0.074 (5)	−0.003 (5)	−0.007 (4)	−0.010 (5)
C26	0.123 (7)	0.142 (8)	0.112 (7)	−0.056 (7)	−0.055 (6)	0.060 (6)
C27	0.107 (7)	0.183 (11)	0.138 (8)	−0.075 (7)	−0.055 (6)	0.060 (7)
C28	0.100 (7)	0.132 (9)	0.097 (7)	0.031 (6)	−0.026 (6)	0.006 (6)
C29	0.149 (9)	0.088 (7)	0.092 (6)	0.008 (7)	−0.028 (6)	0.021 (5)
C30	0.090 (6)	0.056 (6)	0.106 (6)	−0.011 (4)	0.004 (5)	−0.005 (5)
N1	0.072 (4)	0.071 (4)	0.072 (4)	0.026 (3)	−0.018 (3)	−0.016 (3)
N2	0.061 (4)	0.087 (5)	0.081 (4)	0.014 (3)	−0.025 (3)	−0.023 (3)
N3	0.071 (4)	0.081 (5)	0.080 (4)	0.004 (3)	−0.004 (3)	−0.010 (4)
N4	0.088 (4)	0.082 (5)	0.067 (4)	0.009 (4)	−0.021 (3)	−0.016 (4)
S1	0.0782 (13)	0.1111 (17)	0.0922 (14)	0.0329 (12)	−0.0366 (11)	−0.0305 (12)
S2	0.0734 (12)	0.0855 (14)	0.0711 (11)	0.0169 (10)	−0.0206 (9)	−0.0137 (10)
S3	0.0904 (13)	0.1104 (17)	0.0763 (12)	0.0126 (12)	−0.0227 (10)	−0.0276 (12)
S4	0.0794 (12)	0.0836 (14)	0.0674 (11)	−0.0011 (10)	−0.0161 (9)	−0.0111 (10)

Geometric parameters (Å, º)

Br1—C1	1.895 (7)	C16—C17	1.391 (8)
Br2—C16	1.901 (7)	C17—C18	1.397 (8)
C1—C6	1.363 (8)	C17—C22	1.457 (8)
C1—C2	1.379 (8)	C18—C19	1.397 (8)
C2—C3	1.396 (7)	C18—H18A	0.930
C2—C7	1.471 (8)	C19—C20	1.353 (9)
C3—C4	1.372 (8)	C19—H19A	0.930
C3—H3A	0.930	C20—C21	1.366 (9)
C4—C5	1.362 (9)	C20—H20A	0.930
C4—H4A	0.930	C21—H21A	0.930
C5—C6	1.370 (8)	C22—N3	1.257 (7)
C5—H5A	0.930	C22—H22A	0.930
C6—H6A	0.930	C23—N4	1.338 (7)
C7—N1	1.272 (7)	C23—S3	1.650 (6)
C7—H7A	0.930	C23—S4	1.752 (6)
C8—N2	1.324 (6)	C24—C25	1.520 (8)
C8—S1	1.659 (6)	C24—S4	1.808 (6)
C8—S2	1.761 (5)	C24—H24A	0.970
C9—C10	1.502 (7)	C24—H24B	0.970
C9—S2	1.810 (6)	C25—C26	1.339 (8)
C9—H9A	0.970	C25—C30	1.369 (8)
C9—H9B	0.970	C26—C27	1.381 (9)
C10—C11	1.363 (8)	C26—H26A	0.930
C10—C15	1.389 (8)	C27—C28	1.361 (10)
C11—C12	1.373 (9)	C27—H27A	0.930
C11—H11A	0.930	C28—C29	1.320 (10)
C12—C13	1.360 (9)	C28—H28A	0.930
C12—H12A	0.930	C29—C30	1.381 (9)
C13—C14	1.356 (9)	C29—H29A	0.930
C13—H13A	0.930	C30—H30A	0.930
C14—C15	1.359 (8)	N1—N2	1.359 (6)
C14—H14A	0.930	N2—H2	0.860
C15—H15A	0.930	N3—N4	1.364 (6)
C16—C21	1.366 (8)	N4—H4	0.860
C6—C1—C2	120.1 (6)	C18—C17—C22	120.6 (7)
C6—C1—Br1	117.8 (6)	C17—C18—C19	120.1 (7)
C2—C1—Br1	122.1 (6)	C17—C18—H18A	119.9
C1—C2—C3	118.2 (6)	C19—C18—H18A	119.9
C1—C2—C7	121.5 (7)	C20—C19—C18	121.2 (8)
C3—C2—C7	120.2 (6)	C20—C19—H19A	119.4
C4—C3—C2	119.9 (7)	C18—C19—H19A	119.4
C4—C3—H3A	120.0	C19—C20—C21	119.2 (8)
C2—C3—H3A	120.0	C19—C20—H20A	120.4
C5—C4—C3	121.6 (7)	C21—C20—H20A	120.4
C5—C4—H4A	119.2	C20—C21—C16	120.9 (7)
C3—C4—H4A	119.2	C20—C21—H21A	119.5
C4—C5—C6	117.9 (7)	C16—C21—H21A	119.5
C4—C5—H5A	121.0	N3—C22—C17	121.5 (7)
C6—C5—H5A	121.0	N3—C22—H22A	119.2
C1—C6—C5	122.1 (7)	C17—C22—H22A	119.2
C1—C6—H6A	119.0	N4—C23—S3	121.8 (5)
C5—C6—H6A	119.0	N4—C23—S4	112.6 (5)
N1—C7—C2	119.9 (6)	S3—C23—S4	125.6 (5)
N1—C7—H7A	120.0	C25—C24—S4	108.0 (4)
C2—C7—H7A	120.0	C25—C24—H24A	110.1
N2—C8—S1	122.9 (5)	S4—C24—H24A	110.1
N2—C8—S2	112.8 (4)	C25—C24—H24B	110.1
S1—C8—S2	124.3 (4)	S4—C24—H24B	110.1
C10—C9—S2	109.7 (4)	H24A—C24—H24B	108.4
C10—C9—H9A	109.7	C26—C25—C30	117.9 (7)
S2—C9—H9A	109.7	C26—C25—C24	120.9 (8)
C10—C9—H9B	109.7	C30—C25—C24	121.2 (7)
S2—C9—H9B	109.7	C25—C26—C27	121.0 (8)
H9A—C9—H9B	108.2	C25—C26—H26A	119.5
C11—C10—C15	118.7 (6)	C27—C26—H26A	119.5
C11—C10—C9	120.3 (7)	C28—C27—C26	120.6 (8)
C15—C10—C9	120.8 (7)	C28—C27—H27A	119.7
C10—C11—C12	120.5 (7)	C26—C27—H27A	119.7
C10—C11—H11A	119.7	C29—C28—C27	118.8 (8)
C12—C11—H11A	119.7	C29—C28—H28A	120.6
C13—C12—C11	119.5 (7)	C27—C28—H28A	120.6
C13—C12—H12A	120.2	C28—C29—C30	121.1 (8)
C11—C12—H12A	120.2	C28—C29—H29A	119.4
C14—C13—C12	121.0 (8)	C30—C29—H29A	119.4
C14—C13—H13A	119.5	C25—C30—C29	120.7 (7)
C12—C13—H13A	119.5	C25—C30—H30A	119.7
C13—C14—C15	119.6 (7)	C29—C30—H30A	119.7
C13—C14—H14A	120.2	C7—N1—N2	115.6 (5)
C15—C14—H14A	120.2	C8—N2—N1	121.6 (5)
C14—C15—C10	120.6 (6)	C8—N2—H2	119.2
C14—C15—H15A	119.7	N1—N2—H2	119.2
C10—C15—H15A	119.7	C22—N3—N4	115.0 (6)
C21—C16—C17	121.7 (7)	C23—N4—N3	122.8 (6)
C21—C16—Br2	117.2 (7)	C23—N4—H4	118.6
C17—C16—Br2	121.1 (6)	N3—N4—H4	118.6
C16—C17—C18	116.9 (7)	C8—S2—C9	102.0 (3)
C16—C17—C22	122.5 (7)	C23—S4—C24	102.8 (3)
C6—C1—C2—C3	−2.4 (10)	C18—C19—C20—C21	0.4 (13)
Br1—C1—C2—C3	179.6 (5)	C19—C20—C21—C16	0.8 (12)
C6—C1—C2—C7	−179.9 (6)	C17—C16—C21—C20	−1.1 (11)
Br1—C1—C2—C7	2.1 (9)	Br2—C16—C21—C20	177.7 (6)
C1—C2—C3—C4	2.1 (10)	C16—C17—C22—N3	169.0 (6)
C7—C2—C3—C4	179.7 (6)	C18—C17—C22—N3	−10.0 (10)
C2—C3—C4—C5	−2.3 (12)	S4—C24—C25—C26	−75.2 (8)
C3—C4—C5—C6	2.6 (13)	S4—C24—C25—C30	107.2 (6)
C2—C1—C6—C5	2.8 (11)	C30—C25—C26—C27	−1.1 (13)
Br1—C1—C6—C5	−179.1 (6)	C24—C25—C26—C27	−178.8 (7)
C4—C5—C6—C1	−2.8 (12)	C25—C26—C27—C28	1.1 (15)
C1—C2—C7—N1	−172.1 (6)	C26—C27—C28—C29	0.3 (15)
C3—C2—C7—N1	10.5 (10)	C27—C28—C29—C30	−1.6 (14)
S2—C9—C10—C11	68.9 (7)	C26—C25—C30—C29	−0.2 (11)
S2—C9—C10—C15	−115.6 (6)	C24—C25—C30—C29	177.5 (6)
C15—C10—C11—C12	0.0 (10)	C28—C29—C30—C25	1.6 (13)
C9—C10—C11—C12	175.6 (6)	C2—C7—N1—N2	−178.9 (5)
C10—C11—C12—C13	0.9 (11)	S1—C8—N2—N1	−175.6 (5)
C11—C12—C13—C14	−0.8 (12)	S2—C8—N2—N1	2.7 (8)
C12—C13—C14—C15	−0.3 (12)	C7—N1—N2—C8	175.6 (6)
C13—C14—C15—C10	1.3 (11)	C17—C22—N3—N4	178.6 (5)
C11—C10—C15—C14	−1.2 (10)	S3—C23—N4—N3	174.1 (4)
C9—C10—C15—C14	−176.7 (6)	S4—C23—N4—N3	−5.5 (8)
C21—C16—C17—C18	0.2 (10)	C22—N3—N4—C23	−173.9 (6)
Br2—C16—C17—C18	−178.5 (5)	N2—C8—S2—C9	178.8 (5)
C21—C16—C17—C22	−178.8 (6)	S1—C8—S2—C9	−2.9 (5)
Br2—C16—C17—C22	2.5 (9)	C10—C9—S2—C8	−170.6 (5)
C16—C17—C18—C19	0.9 (10)	N4—C23—S4—C24	−176.3 (5)
C22—C17—C18—C19	180.0 (7)	S3—C23—S4—C24	4.1 (5)
C17—C18—C19—C20	−1.2 (12)	C25—C24—S4—C23	173.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···S3^i	0.86	2.88	3.669 (5)	154
N2—H2···S1^ii	0.86	2.62	3.455 (5)	164

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