4-Bromo-N-(di-n-propyl-carbamothioyl)-benzamide.

The synthesis of the title compound, C(14)H(19)BrN(2)OS, involves the reaction of 4-bromo-benzoyl chloride with potassium thio-cyanate in acetone followed by condensation of the resulting 4-bromo-benzoyl isothio-cyanate with di-n-propyl-amine. Typical thio-urea carbonyl and thio-carbonyl double bonds, as well as shortened C-N bonds, are observed in the title compound. The short C-N bond lengths in the centre of the mol-ecule reveal the effects of resonance in this part of the mol-ecule. The asymmetric unit of the title compound contains two crystallographically independent mol-ecules, A and B. There is very little difference between the bond lengths and angles of these mol-ecules. In mol-ecule B, one di-n-propyl group is twisted in a -anti-periplanar conformation with C-C-C-H = -179.1 (3)° and the other adopts a -synclinal conformation with C-C-C-H = -56.7 (4)°; in mol-ecule A the two di-n-propyl groups are twisted in + and -anti-periplanar conformations, with C-C-C-H = -179.9 (3) and 178.2 (3)°, respectively. In the crystal, the mol-ecules are linked into dimeric pairs via pairs of N-H⋯S hydrogen bonds.

Related literature

For synthesis, see: Özer et al. (2009 ▶); Mansuroğlu et al. (2008 ▶); Uğur et al. (2006 ▶); Arslan et al. (2003b ▶, 2006 ▶), and references therein. For general background, see: Koch (2001 ▶); El Aamrani et al. (1998 ▶, 1999 ▶); Arslan et al. (2006 ▶, 2007a ▶,b ▶). For related compounds, see: Khawar Rauf et al. (2009a ▶,b ▶,c ▶,d ▶); Arslan et al. (2003a ▶, 2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H19BrN2OS

M = 343.28

Monoclinic,

a = 21.104 (3) Å

b = 9.6940 (12) Å

c = 16.208 (2) Å

β = 108.956 (3)°

V = 3135.9 (7) Å3

Z = 8

Mo Kα radiation

μ = 2.75 mm−1

T = 120 (2) K

0.48 × 0.18 × 0.17 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.352, T max = 0.652

27091 measured reflections

7470 independent reflections

4686 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.094

S = 0.97

7470 reflections

340 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.70 e Å−3

Δρmin = −0.71 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003511/at2717sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003511/at2717Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H19BrN2OS	F(000) = 1408
Mr = 343.28	Dx = 1.454 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 948 reflections
a = 21.104 (3) Å	θ = 2.5–26.5°
b = 9.6940 (12) Å	µ = 2.75 mm−1
c = 16.208 (2) Å	T = 120 K
β = 108.956 (3)°	Needle, colourless
V = 3135.9 (7) Å3	0.48 × 0.18 × 0.17 mm
Z = 8

Bruker SMART APEX diffractometer	7470 independent reflections
Radiation source: sealed tube	4686 reflections with I > 2σ(I)
graphite	Rint = 0.074
φ and ω scans	θmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −27→27
Tmin = 0.352, Tmax = 0.652	k = −12→12
27091 measured reflections	l = −21→21

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)] = 0.043	Hydrogen site location: difference Fourier map
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.0334P)2] where P = (Fo2 + 2Fc2)/3
7470 reflections	(Δ/σ)max = 0.001
340 parameters	Δρmax = 1.70 e Å−3
2 restraints	Δρmin = −0.71 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.721214 (18)	1.21378 (4)	0.60004 (2)	0.03477 (11)
S1	0.83552 (4)	0.37951 (8)	0.86296 (5)	0.02170 (19)
O1	0.93367 (10)	0.7028 (2)	0.81254 (14)	0.0262 (5)
N11	0.84288 (12)	0.5668 (3)	0.74656 (17)	0.0183 (6)
H1	0.7986 (4)	0.576 (3)	0.735 (2)	0.028 (7)*
N12	0.92646 (12)	0.4005 (3)	0.78106 (16)	0.0204 (6)
C101	0.87200 (14)	0.4481 (3)	0.79479 (19)	0.0184 (7)
C102	0.94737 (15)	0.4434 (3)	0.7063 (2)	0.0236 (7)
H10A	0.9965	0.4320	0.7216	0.028*
H10B	0.9368	0.5423	0.6940	0.028*
C103	0.91272 (16)	0.3599 (4)	0.6251 (2)	0.0277 (8)
H10C	0.9227	0.2608	0.6378	0.033*
H10D	0.8637	0.3724	0.6093	0.033*
C104	0.93463 (18)	0.4015 (4)	0.5486 (2)	0.0384 (10)
H10E	0.9111	0.3449	0.4978	0.058*
H10F	0.9831	0.3877	0.5635	0.058*
H10G	0.9239	0.4990	0.5349	0.058*
C105	0.96618 (15)	0.2880 (3)	0.8356 (2)	0.0263 (8)
H10H	0.9928	0.2415	0.8034	0.032*
H10I	0.9353	0.2190	0.8467	0.032*
C106	1.01386 (16)	0.3413 (4)	0.9236 (2)	0.0321 (9)
H10J	0.9868	0.3788	0.9581	0.039*
H10K	1.0402	0.2627	0.9564	0.039*
C107	1.06118 (17)	0.4506 (4)	0.9145 (2)	0.0366 (9)
H10L	1.0897	0.4801	0.9726	0.055*
H10M	1.0356	0.5298	0.8831	0.055*
H10N	1.0893	0.4136	0.8820	0.055*
C108	0.87557 (15)	0.6931 (3)	0.76526 (19)	0.0190 (7)
C109	0.83589 (14)	0.8153 (3)	0.7228 (2)	0.0177 (7)
C110	0.85099 (15)	0.9410 (3)	0.7660 (2)	0.0206 (7)
H11A	0.8851	0.9452	0.8212	0.025*
C111	0.81746 (15)	1.0591 (3)	0.7303 (2)	0.0235 (7)
H11B	0.8271	1.1444	0.7606	0.028*
C112	0.76883 (16)	1.0505 (3)	0.6482 (2)	0.0231 (7)
C113	0.75382 (16)	0.9288 (3)	0.6034 (2)	0.0242 (7)
H11C	0.7211	0.9258	0.5471	0.029*
C114	0.78710 (15)	0.8097 (3)	0.6416 (2)	0.0217 (7)
H11D	0.7764	0.7240	0.6118	0.026*
Br2	0.784401 (18)	−0.25845 (4)	0.91522 (2)	0.03427 (11)
S2	0.67033 (4)	0.57023 (9)	0.65301 (5)	0.02282 (19)
O2	0.57058 (10)	0.2585 (2)	0.71095 (15)	0.0286 (5)
N21	0.66312 (12)	0.3906 (3)	0.77447 (17)	0.0205 (6)
H2	0.7080 (3)	0.387 (3)	0.7894 (19)	0.028 (7)*
N22	0.58075 (12)	0.5590 (3)	0.73746 (17)	0.0211 (6)
C201	0.63477 (15)	0.5074 (3)	0.7239 (2)	0.0198 (7)
C202	0.53743 (15)	0.6593 (4)	0.6759 (2)	0.0269 (8)
H20A	0.5640	0.7136	0.6470	0.032*
H20B	0.5167	0.7236	0.7072	0.032*
C203	0.4815 (2)	0.5730 (5)	0.6062 (3)	0.0590 (12)*
H20C	0.5028	0.5082	0.5760	0.071*
H20D	0.4557	0.5184	0.6359	0.071*
C204	0.4363 (2)	0.6658 (5)	0.5424 (3)	0.0759 (15)*
H20E	0.4023	0.6114	0.4990	0.114*
H20F	0.4620	0.7201	0.5133	0.114*
H20G	0.4143	0.7280	0.5723	0.114*
C205	0.55988 (16)	0.5263 (3)	0.8138 (2)	0.0265 (8)
H20H	0.5752	0.4323	0.8348	0.032*
H20I	0.5104	0.5281	0.7965	0.032*
C206	0.58920 (17)	0.6295 (4)	0.8863 (2)	0.0324 (9)
H20J	0.5752	0.7236	0.8643	0.039*
H20K	0.6387	0.6253	0.9045	0.039*
C207	0.56663 (19)	0.6012 (4)	0.9654 (2)	0.0459 (11)
H20L	0.5861	0.6705	1.0105	0.069*
H20M	0.5817	0.5092	0.9885	0.069*
H20N	0.5176	0.6059	0.9477	0.069*
C208	0.62915 (15)	0.2660 (3)	0.7571 (2)	0.0211 (7)
C209	0.66820 (15)	0.1411 (3)	0.7984 (2)	0.0204 (7)
C210	0.65274 (16)	0.0172 (3)	0.7536 (2)	0.0224 (7)
H21A	0.6184	0.0143	0.6985	0.027*
C211	0.68704 (16)	−0.1023 (3)	0.7884 (2)	0.0238 (7)
H21B	0.6773	−0.1870	0.7574	0.029*
C212	0.73567 (16)	−0.0953 (3)	0.8693 (2)	0.0243 (8)
C213	0.75084 (16)	0.0257 (3)	0.9163 (2)	0.0253 (8)
H21C	0.7836	0.0272	0.9727	0.030*
C214	0.71721 (15)	0.1455 (3)	0.8796 (2)	0.0234 (7)
H21D	0.7278	0.2304	0.9102	0.028*

	U11	U22	U33	U12	U13	U23
Br1	0.0403 (2)	0.0273 (2)	0.0392 (2)	0.01111 (16)	0.01621 (18)	0.01217 (16)
S1	0.0196 (4)	0.0208 (5)	0.0249 (4)	−0.0010 (3)	0.0076 (4)	0.0011 (3)
O1	0.0162 (12)	0.0206 (13)	0.0367 (14)	−0.0004 (9)	0.0017 (11)	−0.0033 (10)
N11	0.0116 (13)	0.0164 (15)	0.0267 (15)	−0.0002 (11)	0.0060 (12)	0.0009 (12)
N12	0.0174 (14)	0.0166 (15)	0.0272 (15)	0.0022 (11)	0.0073 (12)	0.0000 (12)
C101	0.0158 (16)	0.0162 (17)	0.0204 (16)	−0.0021 (13)	0.0017 (13)	−0.0050 (13)
C102	0.0209 (17)	0.0221 (19)	0.0317 (19)	0.0003 (14)	0.0137 (15)	−0.0016 (15)
C103	0.0283 (19)	0.025 (2)	0.0284 (19)	−0.0011 (15)	0.0067 (16)	−0.0041 (15)
C104	0.039 (2)	0.048 (3)	0.029 (2)	−0.0021 (18)	0.0125 (18)	−0.0080 (18)
C105	0.0205 (17)	0.022 (2)	0.035 (2)	0.0064 (14)	0.0067 (15)	0.0009 (15)
C106	0.0219 (18)	0.033 (2)	0.038 (2)	0.0077 (16)	0.0042 (17)	0.0048 (17)
C107	0.0246 (19)	0.040 (2)	0.042 (2)	0.0011 (17)	0.0066 (17)	−0.0095 (18)
C108	0.0212 (18)	0.0187 (18)	0.0202 (17)	−0.0016 (14)	0.0112 (15)	−0.0038 (13)
C109	0.0157 (16)	0.0189 (18)	0.0224 (17)	−0.0002 (13)	0.0118 (14)	0.0021 (13)
C110	0.0195 (17)	0.0199 (19)	0.0227 (17)	−0.0040 (14)	0.0074 (14)	−0.0020 (14)
C111	0.0244 (18)	0.0206 (19)	0.0284 (18)	0.0001 (14)	0.0126 (15)	−0.0041 (15)
C112	0.0275 (18)	0.0176 (19)	0.0282 (19)	0.0062 (14)	0.0147 (16)	0.0082 (14)
C113	0.0221 (18)	0.029 (2)	0.0201 (17)	0.0004 (15)	0.0053 (14)	0.0002 (15)
C114	0.0231 (18)	0.0190 (19)	0.0259 (18)	−0.0035 (13)	0.0119 (15)	−0.0024 (14)
Br2	0.0420 (2)	0.0286 (2)	0.0375 (2)	0.01163 (17)	0.02020 (18)	0.01355 (17)
S2	0.0195 (4)	0.0242 (5)	0.0263 (4)	0.0003 (3)	0.0095 (4)	−0.0001 (4)
O2	0.0177 (12)	0.0221 (14)	0.0438 (14)	−0.0028 (10)	0.0068 (11)	−0.0020 (11)
N21	0.0155 (14)	0.0159 (15)	0.0304 (16)	0.0008 (11)	0.0076 (13)	−0.0001 (12)
N22	0.0177 (14)	0.0178 (15)	0.0284 (15)	0.0032 (11)	0.0085 (12)	−0.0002 (12)
C201	0.0156 (16)	0.0183 (18)	0.0231 (17)	−0.0028 (13)	0.0030 (14)	−0.0053 (14)
C202	0.0212 (18)	0.033 (2)	0.0246 (19)	0.0117 (15)	0.0048 (15)	0.0006 (15)
C205	0.0226 (18)	0.026 (2)	0.037 (2)	0.0044 (14)	0.0175 (16)	0.0030 (16)
C206	0.031 (2)	0.040 (2)	0.0271 (19)	−0.0021 (17)	0.0097 (16)	−0.0020 (17)
C207	0.044 (2)	0.062 (3)	0.036 (2)	0.002 (2)	0.020 (2)	−0.001 (2)
C208	0.0196 (17)	0.0200 (19)	0.0270 (17)	0.0001 (14)	0.0121 (15)	−0.0032 (14)
C209	0.0196 (17)	0.0163 (18)	0.0287 (18)	−0.0016 (13)	0.0123 (15)	−0.0001 (14)
C210	0.0209 (18)	0.024 (2)	0.0232 (17)	−0.0030 (14)	0.0080 (15)	−0.0005 (14)
C211	0.0298 (19)	0.0175 (19)	0.0277 (19)	0.0000 (14)	0.0140 (16)	−0.0014 (14)
C212	0.0262 (18)	0.021 (2)	0.0311 (19)	0.0042 (15)	0.0171 (16)	0.0084 (15)
C213	0.0262 (19)	0.025 (2)	0.0249 (18)	−0.0016 (15)	0.0079 (15)	0.0005 (15)
C214	0.0271 (19)	0.0182 (19)	0.0278 (19)	−0.0034 (14)	0.0130 (16)	−0.0031 (15)

Br1—C112	1.901 (3)	Br2—C212	1.902 (3)
S1—C101	1.676 (3)	S2—C201	1.678 (3)
O1—C108	1.220 (3)	O2—C208	1.221 (3)
N11—C108	1.389 (4)	N21—C208	1.386 (4)
N11—C101	1.415 (4)	N21—C201	1.412 (4)
N11—H1	0.896 (15)	N21—H2	0.899 (14)
N12—C101	1.323 (4)	N22—C201	1.327 (4)
N12—C102	1.478 (4)	N22—C205	1.476 (4)
N12—C105	1.481 (4)	N22—C202	1.477 (4)
C102—C103	1.515 (4)	C202—C203	1.582 (5)
C102—H10A	0.9900	C202—H20A	0.9900
C102—H10B	0.9900	C202—H20B	0.9900
C103—C104	1.512 (4)	C203—C204	1.465 (6)
C103—H10C	0.9900	C203—H20C	0.9900
C103—H10D	0.9900	C203—H20D	0.9900
C104—H10E	0.9800	C204—H20E	0.9800
C104—H10F	0.9800	C204—H20F	0.9800
C104—H10G	0.9800	C204—H20G	0.9800
C105—C106	1.543 (4)	C205—C206	1.515 (4)
C105—H10H	0.9900	C205—H20H	0.9900
C105—H10I	0.9900	C205—H20I	0.9900
C106—C107	1.495 (5)	C206—C207	1.529 (4)
C106—H10J	0.9900	C206—H20J	0.9900
C106—H10K	0.9900	C206—H20K	0.9900
C107—H10L	0.9800	C207—H20L	0.9800
C107—H10M	0.9800	C207—H20M	0.9800
C107—H10N	0.9800	C207—H20N	0.9800
C108—C109	1.484 (4)	C208—C209	1.495 (4)
C109—C114	1.384 (4)	C209—C214	1.385 (4)
C109—C110	1.390 (4)	C209—C210	1.387 (4)
C110—C111	1.371 (4)	C210—C211	1.386 (4)
C110—H11A	0.9500	C210—H21A	0.9500
C111—C112	1.394 (4)	C211—C212	1.380 (4)
C111—H11B	0.9500	C211—H21B	0.9500
C112—C113	1.367 (4)	C212—C213	1.379 (4)
C113—C114	1.388 (4)	C213—C214	1.390 (4)
C113—H11C	0.9500	C213—H21C	0.9500
C114—H11D	0.9500	C214—H21D	0.9500
C108—N11—C101	120.0 (2)	C208—N21—C201	119.2 (3)
C108—N11—H1	112 (2)	C208—N21—H2	117 (2)
C101—N11—H1	116 (2)	C201—N21—H2	114 (2)
C101—N12—C102	123.2 (3)	C201—N22—C205	124.3 (3)
C101—N12—C105	120.7 (3)	C201—N22—C202	120.9 (3)
C102—N12—C105	115.8 (2)	C205—N22—C202	114.8 (2)
N12—C101—N11	115.8 (3)	N22—C201—N21	115.6 (3)
N12—C101—S1	125.7 (2)	N22—C201—S2	125.2 (2)
N11—C101—S1	118.5 (2)	N21—C201—S2	119.3 (2)
N12—C102—C103	111.9 (2)	N22—C202—C203	106.8 (3)
N12—C102—H10A	109.2	N22—C202—H20A	110.4
C103—C102—H10A	109.2	C203—C202—H20A	110.4
N12—C102—H10B	109.2	N22—C202—H20B	110.4
C103—C102—H10B	109.2	C203—C202—H20B	110.4
H10A—C102—H10B	107.9	H20A—C202—H20B	108.6
C104—C103—C102	112.3 (3)	C204—C203—C202	110.1 (4)
C104—C103—H10C	109.1	C204—C203—H20C	109.6
C102—C103—H10C	109.1	C202—C203—H20C	109.6
C104—C103—H10D	109.1	C204—C203—H20D	109.6
C102—C103—H10D	109.1	C202—C203—H20D	109.6
H10C—C103—H10D	107.9	H20C—C203—H20D	108.2
C103—C104—H10E	109.5	C203—C204—H20E	109.5
C103—C104—H10F	109.5	C203—C204—H20F	109.5
H10E—C104—H10F	109.5	H20E—C204—H20F	109.5
C103—C104—H10G	109.5	C203—C204—H20G	109.5
H10E—C104—H10G	109.5	H20E—C204—H20G	109.5
H10F—C104—H10G	109.5	H20F—C204—H20G	109.5
N12—C105—C106	112.2 (3)	N22—C205—C206	110.5 (3)
N12—C105—H10H	109.2	N22—C205—H20H	109.5
C106—C105—H10H	109.2	C206—C205—H20H	109.5
N12—C105—H10I	109.2	N22—C205—H20I	109.5
C106—C105—H10I	109.2	C206—C205—H20I	109.5
H10H—C105—H10I	107.9	H20H—C205—H20I	108.1
C107—C106—C105	113.8 (3)	C205—C206—C207	111.9 (3)
C107—C106—H10J	108.8	C205—C206—H20J	109.2
C105—C106—H10J	108.8	C207—C206—H20J	109.2
C107—C106—H10K	108.8	C205—C206—H20K	109.2
C105—C106—H10K	108.8	C207—C206—H20K	109.2
H10J—C106—H10K	107.7	H20J—C206—H20K	107.9
C106—C107—H10L	109.5	C206—C207—H20L	109.5
C106—C107—H10M	109.5	C206—C207—H20M	109.5
H10L—C107—H10M	109.5	H20L—C207—H20M	109.5
C106—C107—H10N	109.5	C206—C207—H20N	109.5
H10L—C107—H10N	109.5	H20L—C207—H20N	109.5
H10M—C107—H10N	109.5	H20M—C207—H20N	109.5
O1—C108—N11	122.1 (3)	O2—C208—N21	122.1 (3)
O1—C108—C109	122.0 (3)	O2—C208—C209	121.8 (3)
N11—C108—C109	115.9 (3)	N21—C208—C209	116.2 (3)
C114—C109—C110	119.4 (3)	C214—C209—C210	120.0 (3)
C114—C109—C108	122.9 (3)	C214—C209—C208	122.3 (3)
C110—C109—C108	117.6 (3)	C210—C209—C208	117.7 (3)
C111—C110—C109	121.1 (3)	C211—C210—C209	120.5 (3)
C111—C110—H11A	119.4	C211—C210—H21A	119.7
C109—C110—H11A	119.4	C209—C210—H21A	119.7
C110—C111—C112	118.2 (3)	C212—C211—C210	118.4 (3)
C110—C111—H11B	120.9	C212—C211—H21B	120.8
C112—C111—H11B	120.9	C210—C211—H21B	120.8
C113—C112—C111	122.0 (3)	C213—C212—C211	122.3 (3)
C113—C112—Br1	120.0 (2)	C213—C212—Br2	119.5 (3)
C111—C112—Br1	117.9 (2)	C211—C212—Br2	118.1 (2)
C112—C113—C114	119.0 (3)	C212—C213—C214	118.7 (3)
C112—C113—H11C	120.5	C212—C213—H21C	120.7
C114—C113—H11C	120.5	C214—C213—H21C	120.7
C109—C114—C113	120.2 (3)	C209—C214—C213	120.1 (3)
C109—C114—H11D	119.9	C209—C214—H21D	120.0
C113—C114—H11D	119.9	C213—C214—H21D	120.0
C102—N12—C101—N11	−14.7 (4)	C205—N22—C201—N21	15.9 (4)
C105—N12—C101—N11	172.2 (3)	C202—N22—C201—N21	−165.8 (3)
C102—N12—C101—S1	165.0 (2)	C205—N22—C201—S2	−164.0 (2)
C105—N12—C101—S1	−8.1 (4)	C202—N22—C201—S2	14.2 (4)
C108—N11—C101—N12	−69.6 (4)	C208—N21—C201—N22	70.4 (4)
C108—N11—C101—S1	110.7 (3)	C208—N21—C201—S2	−109.6 (3)
C101—N12—C102—C103	−84.6 (4)	C201—N22—C202—C203	91.1 (3)
C105—N12—C102—C103	88.8 (3)	C205—N22—C202—C203	−90.5 (3)
N12—C102—C103—C104	−179.1 (3)	N22—C202—C203—C204	−179.9 (3)
C101—N12—C105—C106	−81.1 (4)	C201—N22—C205—C206	91.7 (4)
C102—N12—C105—C106	105.3 (3)	C202—N22—C205—C206	−86.6 (3)
N12—C105—C106—C107	−56.6 (4)	N22—C205—C206—C207	178.1 (3)
C101—N11—C108—O1	11.9 (4)	C201—N21—C208—O2	−13.6 (4)
C101—N11—C108—C109	−169.3 (2)	C201—N21—C208—C209	166.7 (3)
O1—C108—C109—C114	147.1 (3)	O2—C208—C209—C214	−146.2 (3)
N11—C108—C109—C114	−31.8 (4)	N21—C208—C209—C214	33.6 (4)
O1—C108—C109—C110	−30.3 (4)	O2—C208—C209—C210	32.2 (4)
N11—C108—C109—C110	150.9 (3)	N21—C208—C209—C210	−148.1 (3)
C114—C109—C110—C111	1.3 (4)	C214—C209—C210—C211	−1.5 (4)
C108—C109—C110—C111	178.7 (3)	C208—C209—C210—C211	−179.9 (3)
C109—C110—C111—C112	−1.6 (4)	C209—C210—C211—C212	1.4 (4)
C110—C111—C112—C113	0.4 (5)	C210—C211—C212—C213	0.3 (5)
C110—C111—C112—Br1	178.7 (2)	C210—C211—C212—Br2	−178.1 (2)
C111—C112—C113—C114	1.2 (5)	C211—C212—C213—C214	−1.9 (5)
Br1—C112—C113—C114	−177.1 (2)	Br2—C212—C213—C214	176.5 (2)
C110—C109—C114—C113	0.3 (4)	C210—C209—C214—C213	−0.1 (4)
C108—C109—C114—C113	−177.0 (3)	C208—C209—C214—C213	178.2 (3)
C112—C113—C114—C109	−1.6 (4)	C212—C213—C214—C209	1.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H1···S2	0.90 (2)	2.60 (2)	3.460 (3)	161 (3)
N21—H2···S1	0.90 (1)	2.57 (2)	3.452 (3)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N11—H1⋯S2	0.896 (15)	2.600 (19)	3.460 (3)	161 (3)
N21—H2⋯S1	0.899 (14)	2.566 (17)	3.452 (3)	169 (2)