4,5-Dibromo-N-(8-quinol­yl)thio­phene-2-sulfonamide

Silva, L.E. da; Joussef, A.C.; Foro, S.; Schmidt, B.

doi:10.1107/S1600536805041693

4,5-Dibromo-N-(8-quinolyl)thiophene-2-sulfonamide

L. E. da Silva, A. C. Joussef, S. Foro and B. Schmidt

There are two independent molecules in the asymmetric unit of the title compound, C₁₃H₈Br₂N₂O₂S₂. Intermolecular C—H

O hydrogen bonds are observed, linking each non-planar molecule to a symmetry-equivalent molecule.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041693/hg6272sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041693/hg6272Isup2.hkl Contains datablock I

CCDC reference: 296569

checkCIF report

Key indicators

Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.011 Å
R factor = 0.045
wR factor = 0.103
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.62 Ratio
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S4     -   C23     ..       7.10 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S4     -   C26     ..       9.19 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C23    -   C24     ..      13.72 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C24    -   C25     ..       7.16 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         S4
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C24

Alert level C
PLAT213_ALERT_2_C Atom C24     has ADP max/min Ratio .............       3.50 prolat
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.64 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT318_ALERT_2_C Check Hybridisation of  N3     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S4     in Main Residue .          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C24    -   C25    ...       1.53 Ang.
PLAT415_ALERT_2_C Short Inter D-H..H-X       H1N    ..  H3      ..       2.14 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  N4      ..       3.37 Ang.
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.02

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.36
           From the CIF: _reflns_number_total               6068
           Count of symmetry unique reflns         3193
           Completeness (_total/calc)            190.04%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2875
           Fraction of Friedel pairs measured     0.900
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  15 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Zinc fluorophores have recently been attracting much interest in biological and environmental applications. Following carbonic anhydrase based biosensors with fluorescent aromatic sulfonamides, a chemosensor, Zinquin, is now extensively used to study the role of intracellular Zn²⁺ in cellular biology (Kimura & Koike, 1998). Our interest in such metal chelators as potential agents for neuroprotection in Alzheimer's disease (Zheng et al., 2005) led to the X-ray study of the title compound, (I).

The quinoline ring system of each of the two independent molecules in the asymmetric unit (Fig. 1) is nearly planar. The dihedral angles between the quinoline moiety and the thiophene ring, viz. C1—N1—S1—C10 and C14—N3—S3—C23 are 59.7 (6) and 60.3 (7)°, respectively. Molecules of the title compound are linked by intermolecular C—H···O (H···O = 2.51 and 2.60 Å) hydrogen bonds to form a chain, as shown in Fig. 2 and detailed in Table 1. A ratio of 0.23:0.77 (1) for both enantiomers was refined using the TWIN option in SHELXL97 (Sheldrick, 1997).

Experimental top

The title compound, (I), was prepared according to a literature procedure (Xue et al., 2000). Suitable crystals were obtained by recrystallization from methanol–dichloromethane (1:1 v/v).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED-CCD (Oxford Diffraction, 2004); data reduction: CrysAlis RED-CCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The molecular packing of (I), with hydrogen bonds shown as dashed lines.

4,5-Dibromo-N-(8-quinolyl)thiophene-2-sulfonamide top

Crystal data top

C₁₃H₈Br₂N₂O₂S₂	F(000) = 1744
M_r = 448.15	D_x = 1.976 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2740 reflections
a = 28.318 (2) Å	θ = 2.8–18.0°
b = 7.0471 (5) Å	µ = 5.66 mm⁻¹
c = 15.094 (1) Å	T = 299 K
V = 3012.2 (4) Å³	Rod shaped, pink
Z = 8	0.28 × 0.10 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur (TM) diffractometer with Sapphire CCD detector	6068 independent reflections
Radiation source: fine-focus sealed tube	3494 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 4.1°
Absorption correction: analytical (CrysAlis RED-CCD; Oxford Diffraction, 2004)	h = −35→34
T_min = 0.344, T_max = 0.760	k = −5→8
20485 measured reflections	l = −18→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0499P)²] where P = (F_o² + 2F_c²)/3
S = 0.88	(Δ/σ)_max = 0.022
6068 reflections	Δρ_max = 0.69 e Å⁻³
380 parameters	Δρ_min = −0.54 e Å⁻³
2 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

Crystal data top

C₁₃H₈Br₂N₂O₂S₂	V = 3012.2 (4) Å³
M_r = 448.15	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 28.318 (2) Å	µ = 5.66 mm⁻¹
b = 7.0471 (5) Å	T = 299 K
c = 15.094 (1) Å	0.28 × 0.10 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur (TM) diffractometer with Sapphire CCD detector	6068 independent reflections
Absorption correction: analytical (CrysAlis RED-CCD; Oxford Diffraction, 2004)	3494 reflections with I > 2σ(I)
T_min = 0.344, T_max = 0.760	R_int = 0.063
20485 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.103	Δρ_max = 0.69 e Å⁻³
S = 0.88	Δρ_min = −0.54 e Å⁻³
6068 reflections	Absolute structure: Flack (1983)
380 parameters	Absolute structure parameter: 0.00 (2)
2 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.20499 (3)	0.84695 (12)	−0.12857 (6)	0.0771 (3)
Br2	0.19211 (3)	0.36792 (11)	−0.06921 (5)	0.0684 (3)
S1	0.07727 (7)	0.8703 (3)	0.15981 (12)	0.0500 (5)
S2	0.12721 (7)	0.5391 (3)	0.07494 (14)	0.0623 (6)
O1	0.0804 (2)	0.7550 (9)	0.2355 (3)	0.0713 (16)
O2	0.08613 (19)	1.0716 (7)	0.1636 (3)	0.0652 (15)
N1	0.0245 (2)	0.8470 (8)	0.1188 (4)	0.0505 (16)
H1N	0.0083	0.9485	0.1101	0.061*
N2	−0.0264 (2)	0.8417 (8)	−0.0288 (4)	0.0468 (15)
C1	0.0034 (2)	0.6709 (10)	0.0964 (4)	0.0403 (17)
C2	0.0060 (3)	0.5091 (12)	0.1429 (5)	0.053 (2)
H2	0.0225	0.5074	0.1962	0.064*
C3	−0.0158 (3)	0.3417 (12)	0.1126 (6)	0.066 (3)
H3	−0.0129	0.2304	0.1453	0.080*
C4	−0.0403 (3)	0.3412 (11)	0.0377 (6)	0.059 (2)
H4	−0.0540	0.2285	0.0184	0.071*
C5	−0.0462 (2)	0.5075 (10)	−0.0136 (5)	0.0432 (18)
C6	−0.0706 (3)	0.5176 (12)	−0.0947 (5)	0.058 (2)
H6	−0.0853	0.4103	−0.1175	0.069*
C7	−0.0725 (3)	0.6807 (13)	−0.1388 (6)	0.065 (2)
H7	−0.0880	0.6872	−0.1931	0.078*
C8	−0.0517 (3)	0.8390 (11)	−0.1039 (5)	0.055 (2)
H8	−0.0553	0.9527	−0.1344	0.066*
C9	−0.0241 (2)	0.6757 (10)	0.0139 (5)	0.0436 (19)
C10	0.1159 (2)	0.7729 (11)	0.0819 (5)	0.0460 (19)
C11	0.1396 (2)	0.8881 (11)	0.0192 (4)	0.0447 (17)
H11	0.1374	1.0193	0.0138	0.054*
C12	0.1685 (3)	0.7580 (10)	−0.0363 (5)	0.046 (2)
C13	0.1642 (3)	0.5770 (11)	−0.0109 (5)	0.0519 (19)
Br3	0.45484 (4)	0.68714 (14)	0.38690 (7)	0.0905 (3)
Br4	0.43461 (3)	1.16646 (11)	0.33536 (6)	0.0651 (2)
S3	0.32894 (8)	0.6771 (4)	0.09128 (13)	0.0690 (6)
S4	0.37186 (9)	0.9980 (4)	0.19215 (18)	0.0870 (9)
O3	0.3401 (2)	0.4816 (9)	0.0825 (4)	0.0860 (19)
O4	0.3325 (2)	0.8030 (11)	0.0183 (4)	0.097 (2)
N3	0.2738 (2)	0.6835 (10)	0.1291 (4)	0.0562 (18)
H3N	0.2580	0.5796	0.1326	0.067*
N4	0.2233 (2)	0.6656 (9)	0.2732 (4)	0.0492 (16)
C14	0.2527 (3)	0.8519 (11)	0.1551 (5)	0.0520 (19)
C15	0.2555 (3)	1.0245 (14)	0.1120 (6)	0.075 (3)
H15	0.2734	1.0375	0.0608	0.090*
C16	0.2307 (3)	1.1802 (13)	0.1469 (7)	0.076 (3)
H16	0.2321	1.2946	0.1162	0.091*
C17	0.2047 (3)	1.1741 (13)	0.2223 (8)	0.076 (3)
H17	0.1893	1.2813	0.2436	0.091*
C18	0.2020 (3)	0.9968 (11)	0.2680 (5)	0.054 (2)
C19	0.1762 (3)	0.9739 (14)	0.3492 (6)	0.068 (2)
H19	0.1610	1.0765	0.3755	0.082*
C20	0.1745 (3)	0.7990 (15)	0.3865 (6)	0.070 (3)
H20	0.1569	0.7808	0.4378	0.085*
C21	0.1981 (3)	0.6488 (12)	0.3501 (6)	0.063 (2)
H21	0.1971	0.5318	0.3785	0.076*
C22	0.2245 (2)	0.8350 (10)	0.2338 (5)	0.0455 (19)
C23	0.3662 (3)	0.7649 (11)	0.1777 (5)	0.057 (2)
C24	0.39153 (17)	0.6242 (8)	0.2353 (3)	0.0208 (13)
H24	0.3927	0.4923	0.2351	0.025*
C25	0.4148 (3)	0.7743 (11)	0.2946 (4)	0.051 (2)
C26	0.4082 (2)	0.9536 (11)	0.2772 (4)	0.0463 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0719 (6)	0.0824 (6)	0.0769 (6)	−0.0052 (5)	0.0296 (5)	0.0118 (5)
Br2	0.0716 (6)	0.0646 (5)	0.0691 (6)	0.0197 (4)	0.0060 (5)	−0.0014 (5)
S1	0.0464 (11)	0.0664 (14)	0.0374 (10)	−0.0005 (10)	−0.0025 (8)	−0.0073 (9)
S2	0.0639 (15)	0.0593 (13)	0.0637 (14)	0.0082 (11)	0.0095 (10)	0.0107 (11)
O1	0.067 (4)	0.111 (4)	0.035 (3)	0.001 (3)	−0.004 (3)	0.002 (3)
O2	0.071 (4)	0.053 (3)	0.072 (4)	0.002 (3)	−0.011 (3)	−0.021 (3)
N1	0.044 (4)	0.053 (4)	0.055 (4)	0.003 (3)	−0.005 (3)	−0.014 (3)
N2	0.041 (4)	0.046 (4)	0.053 (4)	0.006 (3)	−0.002 (3)	0.001 (3)
C1	0.034 (4)	0.045 (5)	0.042 (4)	0.010 (3)	0.005 (3)	−0.008 (3)
C2	0.052 (5)	0.058 (5)	0.050 (5)	0.008 (4)	0.007 (4)	0.003 (4)
C3	0.078 (7)	0.046 (6)	0.076 (7)	0.014 (5)	0.031 (5)	0.003 (5)
C4	0.070 (6)	0.045 (5)	0.063 (6)	−0.010 (4)	0.015 (5)	−0.016 (5)
C5	0.030 (4)	0.054 (5)	0.045 (4)	−0.001 (4)	0.013 (3)	−0.006 (4)
C6	0.048 (5)	0.061 (5)	0.064 (6)	−0.019 (4)	0.008 (4)	−0.011 (4)
C7	0.053 (5)	0.094 (7)	0.049 (5)	−0.006 (5)	−0.005 (4)	−0.010 (5)
C8	0.057 (5)	0.062 (5)	0.045 (5)	0.019 (4)	0.003 (4)	0.006 (4)
C9	0.035 (4)	0.049 (5)	0.047 (5)	0.006 (3)	0.002 (4)	0.003 (4)
C10	0.031 (4)	0.062 (5)	0.044 (5)	0.004 (3)	−0.015 (4)	−0.007 (4)
C11	0.030 (4)	0.073 (5)	0.031 (4)	−0.004 (4)	0.010 (3)	0.002 (4)
C12	0.031 (4)	0.049 (5)	0.057 (5)	−0.010 (3)	−0.002 (4)	0.011 (4)
C13	0.048 (5)	0.056 (5)	0.052 (5)	0.012 (4)	−0.006 (4)	−0.006 (4)
Br3	0.0864 (7)	0.0897 (7)	0.0954 (8)	−0.0071 (5)	−0.0415 (6)	0.0248 (6)
Br4	0.0620 (5)	0.0654 (5)	0.0680 (5)	−0.0083 (4)	0.0023 (4)	−0.0131 (4)
S3	0.0608 (14)	0.1018 (19)	0.0444 (12)	−0.0130 (13)	0.0035 (10)	−0.0214 (12)
S4	0.084 (2)	0.097 (2)	0.0801 (18)	−0.0153 (16)	−0.0064 (14)	0.0038 (15)
O3	0.080 (4)	0.092 (5)	0.086 (5)	0.006 (3)	0.012 (3)	−0.050 (4)
O4	0.082 (5)	0.171 (7)	0.037 (4)	−0.035 (4)	0.009 (3)	0.001 (4)
N3	0.056 (4)	0.058 (4)	0.055 (4)	−0.018 (3)	−0.002 (3)	−0.019 (3)
N4	0.039 (4)	0.058 (4)	0.051 (4)	−0.007 (3)	−0.003 (3)	−0.003 (3)
C14	0.050 (5)	0.058 (5)	0.048 (4)	−0.003 (4)	−0.021 (4)	−0.004 (5)
C15	0.091 (7)	0.076 (6)	0.057 (5)	−0.036 (6)	−0.023 (5)	0.017 (5)
C16	0.085 (7)	0.054 (6)	0.088 (8)	−0.008 (5)	−0.044 (7)	0.011 (5)
C17	0.082 (7)	0.064 (6)	0.082 (7)	0.002 (5)	−0.036 (6)	−0.006 (5)
C18	0.047 (5)	0.059 (5)	0.055 (5)	0.006 (4)	−0.017 (4)	−0.020 (4)
C19	0.047 (5)	0.086 (6)	0.071 (7)	−0.005 (5)	−0.020 (4)	−0.037 (6)
C20	0.036 (5)	0.114 (8)	0.061 (6)	−0.008 (5)	−0.005 (4)	−0.033 (6)
C21	0.057 (5)	0.070 (5)	0.061 (6)	−0.002 (4)	−0.003 (4)	0.001 (5)
C22	0.036 (4)	0.047 (5)	0.054 (5)	−0.009 (4)	−0.022 (4)	−0.002 (4)
C23	0.051 (5)	0.067 (5)	0.053 (5)	−0.027 (4)	0.005 (4)	−0.021 (4)
C24	0.005 (3)	0.034 (3)	0.024 (3)	−0.003 (2)	−0.006 (2)	0.010 (3)
C25	0.038 (5)	0.074 (6)	0.041 (5)	0.011 (4)	0.003 (3)	0.010 (4)
C26	0.046 (5)	0.057 (5)	0.036 (4)	0.012 (4)	−0.004 (3)	0.008 (4)

Geometric parameters (Å, º) top

Br1—C12	1.845 (7)	Br3—C25	1.897 (7)
Br2—C13	1.889 (7)	Br4—C26	1.893 (8)
S1—O1	1.405 (6)	S3—O4	1.418 (6)
S1—O2	1.442 (5)	S3—O3	1.420 (6)
S1—N1	1.625 (6)	S3—N3	1.662 (6)
S1—C10	1.748 (8)	S3—C23	1.787 (8)
S2—C10	1.681 (8)	S4—C23	1.665 (8)
S2—C13	1.689 (8)	S4—C26	1.674 (7)
N1—C1	1.418 (8)	N3—C14	1.386 (9)
N1—H1N	0.8600	N3—H3N	0.8600
N2—C9	1.338 (8)	N4—C22	1.334 (9)
N2—C8	1.339 (9)	N4—C21	1.366 (10)
C1—C2	1.342 (10)	C14—C15	1.382 (11)
C1—C9	1.469 (10)	C14—C22	1.436 (11)
C2—C3	1.408 (11)	C15—C16	1.405 (13)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.327 (12)	C16—C17	1.356 (14)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.416 (10)	C17—C18	1.429 (12)
C4—H4	0.9300	C17—H17	0.9300
C5—C9	1.404 (10)	C18—C22	1.404 (10)
C5—C6	1.407 (10)	C18—C19	1.436 (11)
C6—C7	1.329 (11)	C19—C20	1.356 (12)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.367 (10)	C20—C21	1.368 (11)
C7—H7	0.9300	C20—H20	0.9300
C8—H8	0.9300	C21—H21	0.9300
C10—C11	1.415 (9)	C23—C24	1.502 (10)
C11—C12	1.487 (10)	C24—C25	1.535 (7)
C11—H11	0.9300	C24—H24	0.9300
C12—C13	1.337 (10)	C25—C26	1.305 (10)

O1—S1—O2	121.7 (3)	O4—S3—O3	121.3 (4)
O1—S1—N1	108.0 (3)	O4—S3—N3	108.4 (4)
O2—S1—N1	105.9 (3)	O3—S3—N3	105.5 (4)
O1—S1—C10	106.3 (4)	O4—S3—C23	108.0 (4)
O2—S1—C10	107.7 (3)	O3—S3—C23	105.8 (4)
N1—S1—C10	106.3 (3)	N3—S3—C23	107.1 (4)
C10—S2—C13	90.6 (4)	C23—S4—C26	88.6 (4)
C1—N1—S1	124.5 (5)	C14—N3—S3	121.7 (5)
C1—N1—H1N	117.7	C14—N3—H3N	119.1
S1—N1—H1N	117.7	S3—N3—H3N	119.1
C9—N2—C8	114.9 (6)	C22—N4—C21	118.0 (7)
C2—C1—N1	126.6 (7)	C15—C14—N3	126.6 (9)
C2—C1—C9	119.5 (7)	C15—C14—C22	119.6 (8)
N1—C1—C9	113.9 (6)	N3—C14—C22	113.8 (7)
C1—C2—C3	121.2 (8)	C14—C15—C16	118.9 (9)
C1—C2—H2	119.4	C14—C15—H15	120.5
C3—C2—H2	119.4	C16—C15—H15	120.5
C4—C3—C2	120.6 (8)	C17—C16—C15	124.1 (9)
C4—C3—H3	119.7	C17—C16—H16	118.0
C2—C3—H3	119.7	C15—C16—H16	118.0
C3—C4—C5	121.8 (8)	C16—C17—C18	117.5 (9)
C3—C4—H4	119.1	C16—C17—H17	121.2
C5—C4—H4	119.1	C18—C17—H17	121.2
C9—C5—C6	115.7 (7)	C22—C18—C17	120.5 (8)
C9—C5—C4	119.0 (7)	C22—C18—C19	117.0 (8)
C6—C5—C4	125.2 (8)	C17—C18—C19	122.5 (8)
C7—C6—C5	120.0 (7)	C20—C19—C18	118.3 (8)
C7—C6—H6	120.0	C20—C19—H19	120.8
C5—C6—H6	120.0	C18—C19—H19	120.8
C6—C7—C8	119.6 (8)	C19—C20—C21	121.3 (9)
C6—C7—H7	120.2	C19—C20—H20	119.4
C8—C7—H7	120.2	C21—C20—H20	119.4
N2—C8—C7	124.6 (7)	N4—C21—C20	122.0 (8)
N2—C8—H8	117.7	N4—C21—H21	119.0
C7—C8—H8	117.7	C20—C21—H21	119.0
N2—C9—C5	125.0 (7)	N4—C22—C18	123.4 (8)
N2—C9—C1	117.0 (6)	N4—C22—C14	117.3 (7)
C5—C9—C1	117.9 (6)	C18—C22—C14	119.2 (7)
C11—C10—S2	115.5 (6)	C24—C23—S4	122.0 (5)
C11—C10—S1	121.4 (6)	C24—C23—S3	118.4 (5)
S2—C10—S1	123.1 (5)	S4—C23—S3	119.6 (5)
C10—C11—C12	106.4 (6)	C23—C24—C25	95.1 (5)
C10—C11—H11	126.8	C23—C24—H24	132.5
C12—C11—H11	126.8	C25—C24—H24	132.5
C13—C12—C11	112.2 (6)	C26—C25—C24	119.2 (6)
C13—C12—Br1	126.2 (6)	C26—C25—Br3	123.2 (5)
C11—C12—Br1	121.6 (5)	C24—C25—Br3	117.5 (5)
C12—C13—S2	115.2 (6)	C25—C26—S4	115.1 (6)
C12—C13—Br2	125.0 (6)	C25—C26—Br4	128.1 (5)
S2—C13—Br2	119.6 (5)	S4—C26—Br4	116.8 (4)

O1—S1—N1—C1	−54.0 (6)	O4—S3—N3—C14	−56.0 (7)
O2—S1—N1—C1	174.1 (5)	O3—S3—N3—C14	172.7 (6)
C10—S1—N1—C1	59.7 (6)	C23—S3—N3—C14	60.3 (7)
S1—N1—C1—C2	40.8 (10)	S3—N3—C14—C15	42.4 (10)
S1—N1—C1—C9	−140.1 (5)	S3—N3—C14—C22	−139.4 (6)
N1—C1—C2—C3	−178.6 (6)	N3—C14—C15—C16	178.4 (7)
C9—C1—C2—C3	2.3 (11)	C22—C14—C15—C16	0.3 (12)
C1—C2—C3—C4	−1.4 (13)	C14—C15—C16—C17	1.8 (14)
C2—C3—C4—C5	−1.0 (12)	C15—C16—C17—C18	−1.1 (13)
C3—C4—C5—C9	2.4 (11)	C16—C17—C18—C22	−1.7 (11)
C3—C4—C5—C6	178.2 (7)	C16—C17—C18—C19	179.1 (7)
C9—C5—C6—C7	−1.7 (10)	C22—C18—C19—C20	−1.1 (10)
C4—C5—C6—C7	−177.6 (7)	C17—C18—C19—C20	178.1 (7)
C5—C6—C7—C8	−1.5 (11)	C18—C19—C20—C21	2.5 (11)
C9—N2—C8—C7	−2.6 (11)	C22—N4—C21—C20	0.4 (10)
C6—C7—C8—N2	3.9 (12)	C19—C20—C21—N4	−2.2 (12)
C8—N2—C9—C5	−1.0 (10)	C21—N4—C22—C18	1.1 (10)
C8—N2—C9—C1	179.7 (6)	C21—N4—C22—C14	177.5 (6)
C6—C5—C9—N2	3.1 (10)	C17—C18—C22—N4	−179.9 (7)
C4—C5—C9—N2	179.3 (7)	C19—C18—C22—N4	−0.7 (11)
C6—C5—C9—C1	−177.6 (6)	C17—C18—C22—C14	3.8 (10)
C4—C5—C9—C1	−1.4 (9)	C19—C18—C22—C14	−177.0 (6)
C2—C1—C9—N2	178.5 (7)	C15—C14—C22—N4	−179.6 (7)
N1—C1—C9—N2	−0.7 (8)	N3—C14—C22—N4	2.1 (9)
C2—C1—C9—C5	−0.9 (10)	C15—C14—C22—C18	−3.0 (10)
N1—C1—C9—C5	179.9 (6)	N3—C14—C22—C18	178.6 (6)
C13—S2—C10—C11	0.3 (5)	C26—S4—C23—C24	−0.6 (6)
C13—S2—C10—S1	179.6 (5)	C26—S4—C23—S3	179.5 (5)
O1—S1—C10—C11	−148.7 (6)	O4—S3—C23—C24	−144.6 (6)
O2—S1—C10—C11	−16.7 (6)	O3—S3—C23—C24	−13.4 (7)
N1—S1—C10—C11	96.5 (6)	N3—S3—C23—C24	98.8 (6)
O1—S1—C10—S2	32.1 (5)	O4—S3—C23—S4	35.3 (6)
O2—S1—C10—S2	164.0 (4)	O3—S3—C23—S4	166.5 (5)
N1—S1—C10—S2	−82.8 (5)	N3—S3—C23—S4	−81.3 (6)
S2—C10—C11—C12	0.1 (7)	S4—C23—C24—C25	1.7 (7)
S1—C10—C11—C12	−179.2 (5)	S3—C23—C24—C25	−178.4 (5)
C10—C11—C12—C13	−0.7 (8)	C23—C24—C25—C26	−2.6 (8)
C10—C11—C12—Br1	179.2 (5)	C23—C24—C25—Br3	−179.5 (5)
C11—C12—C13—S2	1.0 (8)	C24—C25—C26—S4	2.7 (9)
Br1—C12—C13—S2	−178.8 (4)	Br3—C25—C26—S4	179.4 (4)
C11—C12—C13—Br2	175.8 (5)	C24—C25—C26—Br4	−176.9 (5)
Br1—C12—C13—Br2	−4.0 (10)	Br3—C25—C26—Br4	−0.2 (10)
C10—S2—C13—C12	−0.8 (6)	C23—S4—C26—C25	−1.2 (6)
C10—S2—C13—Br2	−175.9 (4)	C23—S4—C26—Br4	178.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.51	3.215 (9)	133
C20—H20···O3ⁱⁱ	0.93	2.60	3.253 (10)	127

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

Experimental details

Crystal data
Chemical formula	C₁₃H₈Br₂N₂O₂S₂
M_r	448.15
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	299
a, b, c (Å)	28.318 (2), 7.0471 (5), 15.094 (1)
V (Å³)	3012.2 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.66
Crystal size (mm)	0.28 × 0.10 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur (TM) diffractometer with Sapphire CCD detector
Absorption correction	Analytical (CrysAlis RED-CCD; Oxford Diffraction, 2004)
T_min, T_max	0.344, 0.760
No. of measured, independent and observed [I > 2σ(I)] reflections	20485, 6068, 3494
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.103, 0.88
No. of reflections	6068
No. of parameters	380
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.54
Absolute structure	Flack (1983)
Absolute structure parameter	0.00 (2)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED-CCD (Oxford Diffraction, 2004), CrysAlis RED-CCD, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.