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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041693/hg6272sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041693/hg6272Isup2.hkl
Contains datablock I

CCDC reference: 296569

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](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).

Refinement top

H atoms were positioned with idealized geometry using a riding model (C—H –= 0.93 Å and N—H = 0.86 Å) and were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

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
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] 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
C13H8Br2N2O2S2F(000) = 1744
Mr = 448.15Dx = 1.976 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2740 reflections
a = 28.318 (2) Åθ = 2.8–18.0°
b = 7.0471 (5) ŵ = 5.66 mm1
c = 15.094 (1) ÅT = 299 K
V = 3012.2 (4) Å3Rod shaped, pink
Z = 80.28 × 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 tube3494 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
Rotation method data acquisition using ω and ϕ scansθmax = 26.4°, θmin = 4.1°
Absorption correction: analytical
(CrysAlis RED-CCD; Oxford Diffraction, 2004)
h = 3534
Tmin = 0.344, Tmax = 0.760k = 58
20485 measured reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0499P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max = 0.022
6068 reflectionsΔρmax = 0.69 e Å3
380 parametersΔρmin = 0.54 e Å3
2 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (2)
Crystal data top
C13H8Br2N2O2S2V = 3012.2 (4) Å3
Mr = 448.15Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 28.318 (2) ŵ = 5.66 mm1
b = 7.0471 (5) ÅT = 299 K
c = 15.094 (1) Å0.28 × 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)
Tmin = 0.344, Tmax = 0.760Rint = 0.063
20485 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.103Δρmax = 0.69 e Å3
S = 0.88Δρmin = 0.54 e Å3
6068 reflectionsAbsolute structure: Flack (1983)
380 parametersAbsolute 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
xyzUiso*/Ueq
Br10.20499 (3)0.84695 (12)0.12857 (6)0.0771 (3)
Br20.19211 (3)0.36792 (11)0.06921 (5)0.0684 (3)
S10.07727 (7)0.8703 (3)0.15981 (12)0.0500 (5)
S20.12721 (7)0.5391 (3)0.07494 (14)0.0623 (6)
O10.0804 (2)0.7550 (9)0.2355 (3)0.0713 (16)
O20.08613 (19)1.0716 (7)0.1636 (3)0.0652 (15)
N10.0245 (2)0.8470 (8)0.1188 (4)0.0505 (16)
H1N0.00830.94850.11010.061*
N20.0264 (2)0.8417 (8)0.0288 (4)0.0468 (15)
C10.0034 (2)0.6709 (10)0.0964 (4)0.0403 (17)
C20.0060 (3)0.5091 (12)0.1429 (5)0.053 (2)
H20.02250.50740.19620.064*
C30.0158 (3)0.3417 (12)0.1126 (6)0.066 (3)
H30.01290.23040.14530.080*
C40.0403 (3)0.3412 (11)0.0377 (6)0.059 (2)
H40.05400.22850.01840.071*
C50.0462 (2)0.5075 (10)0.0136 (5)0.0432 (18)
C60.0706 (3)0.5176 (12)0.0947 (5)0.058 (2)
H60.08530.41030.11750.069*
C70.0725 (3)0.6807 (13)0.1388 (6)0.065 (2)
H70.08800.68720.19310.078*
C80.0517 (3)0.8390 (11)0.1039 (5)0.055 (2)
H80.05530.95270.13440.066*
C90.0241 (2)0.6757 (10)0.0139 (5)0.0436 (19)
C100.1159 (2)0.7729 (11)0.0819 (5)0.0460 (19)
C110.1396 (2)0.8881 (11)0.0192 (4)0.0447 (17)
H110.13741.01930.01380.054*
C120.1685 (3)0.7580 (10)0.0363 (5)0.046 (2)
C130.1642 (3)0.5770 (11)0.0109 (5)0.0519 (19)
Br30.45484 (4)0.68714 (14)0.38690 (7)0.0905 (3)
Br40.43461 (3)1.16646 (11)0.33536 (6)0.0651 (2)
S30.32894 (8)0.6771 (4)0.09128 (13)0.0690 (6)
S40.37186 (9)0.9980 (4)0.19215 (18)0.0870 (9)
O30.3401 (2)0.4816 (9)0.0825 (4)0.0860 (19)
O40.3325 (2)0.8030 (11)0.0183 (4)0.097 (2)
N30.2738 (2)0.6835 (10)0.1291 (4)0.0562 (18)
H3N0.25800.57960.13260.067*
N40.2233 (2)0.6656 (9)0.2732 (4)0.0492 (16)
C140.2527 (3)0.8519 (11)0.1551 (5)0.0520 (19)
C150.2555 (3)1.0245 (14)0.1120 (6)0.075 (3)
H150.27341.03750.06080.090*
C160.2307 (3)1.1802 (13)0.1469 (7)0.076 (3)
H160.23211.29460.11620.091*
C170.2047 (3)1.1741 (13)0.2223 (8)0.076 (3)
H170.18931.28130.24360.091*
C180.2020 (3)0.9968 (11)0.2680 (5)0.054 (2)
C190.1762 (3)0.9739 (14)0.3492 (6)0.068 (2)
H190.16101.07650.37550.082*
C200.1745 (3)0.7990 (15)0.3865 (6)0.070 (3)
H200.15690.78080.43780.085*
C210.1981 (3)0.6488 (12)0.3501 (6)0.063 (2)
H210.19710.53180.37850.076*
C220.2245 (2)0.8350 (10)0.2338 (5)0.0455 (19)
C230.3662 (3)0.7649 (11)0.1777 (5)0.057 (2)
C240.39153 (17)0.6242 (8)0.2353 (3)0.0208 (13)
H240.39270.49230.23510.025*
C250.4148 (3)0.7743 (11)0.2946 (4)0.051 (2)
C260.4082 (2)0.9536 (11)0.2772 (4)0.0463 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0719 (6)0.0824 (6)0.0769 (6)0.0052 (5)0.0296 (5)0.0118 (5)
Br20.0716 (6)0.0646 (5)0.0691 (6)0.0197 (4)0.0060 (5)0.0014 (5)
S10.0464 (11)0.0664 (14)0.0374 (10)0.0005 (10)0.0025 (8)0.0073 (9)
S20.0639 (15)0.0593 (13)0.0637 (14)0.0082 (11)0.0095 (10)0.0107 (11)
O10.067 (4)0.111 (4)0.035 (3)0.001 (3)0.004 (3)0.002 (3)
O20.071 (4)0.053 (3)0.072 (4)0.002 (3)0.011 (3)0.021 (3)
N10.044 (4)0.053 (4)0.055 (4)0.003 (3)0.005 (3)0.014 (3)
N20.041 (4)0.046 (4)0.053 (4)0.006 (3)0.002 (3)0.001 (3)
C10.034 (4)0.045 (5)0.042 (4)0.010 (3)0.005 (3)0.008 (3)
C20.052 (5)0.058 (5)0.050 (5)0.008 (4)0.007 (4)0.003 (4)
C30.078 (7)0.046 (6)0.076 (7)0.014 (5)0.031 (5)0.003 (5)
C40.070 (6)0.045 (5)0.063 (6)0.010 (4)0.015 (5)0.016 (5)
C50.030 (4)0.054 (5)0.045 (4)0.001 (4)0.013 (3)0.006 (4)
C60.048 (5)0.061 (5)0.064 (6)0.019 (4)0.008 (4)0.011 (4)
C70.053 (5)0.094 (7)0.049 (5)0.006 (5)0.005 (4)0.010 (5)
C80.057 (5)0.062 (5)0.045 (5)0.019 (4)0.003 (4)0.006 (4)
C90.035 (4)0.049 (5)0.047 (5)0.006 (3)0.002 (4)0.003 (4)
C100.031 (4)0.062 (5)0.044 (5)0.004 (3)0.015 (4)0.007 (4)
C110.030 (4)0.073 (5)0.031 (4)0.004 (4)0.010 (3)0.002 (4)
C120.031 (4)0.049 (5)0.057 (5)0.010 (3)0.002 (4)0.011 (4)
C130.048 (5)0.056 (5)0.052 (5)0.012 (4)0.006 (4)0.006 (4)
Br30.0864 (7)0.0897 (7)0.0954 (8)0.0071 (5)0.0415 (6)0.0248 (6)
Br40.0620 (5)0.0654 (5)0.0680 (5)0.0083 (4)0.0023 (4)0.0131 (4)
S30.0608 (14)0.1018 (19)0.0444 (12)0.0130 (13)0.0035 (10)0.0214 (12)
S40.084 (2)0.097 (2)0.0801 (18)0.0153 (16)0.0064 (14)0.0038 (15)
O30.080 (4)0.092 (5)0.086 (5)0.006 (3)0.012 (3)0.050 (4)
O40.082 (5)0.171 (7)0.037 (4)0.035 (4)0.009 (3)0.001 (4)
N30.056 (4)0.058 (4)0.055 (4)0.018 (3)0.002 (3)0.019 (3)
N40.039 (4)0.058 (4)0.051 (4)0.007 (3)0.003 (3)0.003 (3)
C140.050 (5)0.058 (5)0.048 (4)0.003 (4)0.021 (4)0.004 (5)
C150.091 (7)0.076 (6)0.057 (5)0.036 (6)0.023 (5)0.017 (5)
C160.085 (7)0.054 (6)0.088 (8)0.008 (5)0.044 (7)0.011 (5)
C170.082 (7)0.064 (6)0.082 (7)0.002 (5)0.036 (6)0.006 (5)
C180.047 (5)0.059 (5)0.055 (5)0.006 (4)0.017 (4)0.020 (4)
C190.047 (5)0.086 (6)0.071 (7)0.005 (5)0.020 (4)0.037 (6)
C200.036 (5)0.114 (8)0.061 (6)0.008 (5)0.005 (4)0.033 (6)
C210.057 (5)0.070 (5)0.061 (6)0.002 (4)0.003 (4)0.001 (5)
C220.036 (4)0.047 (5)0.054 (5)0.009 (4)0.022 (4)0.002 (4)
C230.051 (5)0.067 (5)0.053 (5)0.027 (4)0.005 (4)0.021 (4)
C240.005 (3)0.034 (3)0.024 (3)0.003 (2)0.006 (2)0.010 (3)
C250.038 (5)0.074 (6)0.041 (5)0.011 (4)0.003 (3)0.010 (4)
C260.046 (5)0.057 (5)0.036 (4)0.012 (4)0.004 (3)0.008 (4)
Geometric parameters (Å, º) top
Br1—C121.845 (7)Br3—C251.897 (7)
Br2—C131.889 (7)Br4—C261.893 (8)
S1—O11.405 (6)S3—O41.418 (6)
S1—O21.442 (5)S3—O31.420 (6)
S1—N11.625 (6)S3—N31.662 (6)
S1—C101.748 (8)S3—C231.787 (8)
S2—C101.681 (8)S4—C231.665 (8)
S2—C131.689 (8)S4—C261.674 (7)
N1—C11.418 (8)N3—C141.386 (9)
N1—H1N0.8600N3—H3N0.8600
N2—C91.338 (8)N4—C221.334 (9)
N2—C81.339 (9)N4—C211.366 (10)
C1—C21.342 (10)C14—C151.382 (11)
C1—C91.469 (10)C14—C221.436 (11)
C2—C31.408 (11)C15—C161.405 (13)
C2—H20.9300C15—H150.9300
C3—C41.327 (12)C16—C171.356 (14)
C3—H30.9300C16—H160.9300
C4—C51.416 (10)C17—C181.429 (12)
C4—H40.9300C17—H170.9300
C5—C91.404 (10)C18—C221.404 (10)
C5—C61.407 (10)C18—C191.436 (11)
C6—C71.329 (11)C19—C201.356 (12)
C6—H60.9300C19—H190.9300
C7—C81.367 (10)C20—C211.368 (11)
C7—H70.9300C20—H200.9300
C8—H80.9300C21—H210.9300
C10—C111.415 (9)C23—C241.502 (10)
C11—C121.487 (10)C24—C251.535 (7)
C11—H110.9300C24—H240.9300
C12—C131.337 (10)C25—C261.305 (10)
O1—S1—O2121.7 (3)O4—S3—O3121.3 (4)
O1—S1—N1108.0 (3)O4—S3—N3108.4 (4)
O2—S1—N1105.9 (3)O3—S3—N3105.5 (4)
O1—S1—C10106.3 (4)O4—S3—C23108.0 (4)
O2—S1—C10107.7 (3)O3—S3—C23105.8 (4)
N1—S1—C10106.3 (3)N3—S3—C23107.1 (4)
C10—S2—C1390.6 (4)C23—S4—C2688.6 (4)
C1—N1—S1124.5 (5)C14—N3—S3121.7 (5)
C1—N1—H1N117.7C14—N3—H3N119.1
S1—N1—H1N117.7S3—N3—H3N119.1
C9—N2—C8114.9 (6)C22—N4—C21118.0 (7)
C2—C1—N1126.6 (7)C15—C14—N3126.6 (9)
C2—C1—C9119.5 (7)C15—C14—C22119.6 (8)
N1—C1—C9113.9 (6)N3—C14—C22113.8 (7)
C1—C2—C3121.2 (8)C14—C15—C16118.9 (9)
C1—C2—H2119.4C14—C15—H15120.5
C3—C2—H2119.4C16—C15—H15120.5
C4—C3—C2120.6 (8)C17—C16—C15124.1 (9)
C4—C3—H3119.7C17—C16—H16118.0
C2—C3—H3119.7C15—C16—H16118.0
C3—C4—C5121.8 (8)C16—C17—C18117.5 (9)
C3—C4—H4119.1C16—C17—H17121.2
C5—C4—H4119.1C18—C17—H17121.2
C9—C5—C6115.7 (7)C22—C18—C17120.5 (8)
C9—C5—C4119.0 (7)C22—C18—C19117.0 (8)
C6—C5—C4125.2 (8)C17—C18—C19122.5 (8)
C7—C6—C5120.0 (7)C20—C19—C18118.3 (8)
C7—C6—H6120.0C20—C19—H19120.8
C5—C6—H6120.0C18—C19—H19120.8
C6—C7—C8119.6 (8)C19—C20—C21121.3 (9)
C6—C7—H7120.2C19—C20—H20119.4
C8—C7—H7120.2C21—C20—H20119.4
N2—C8—C7124.6 (7)N4—C21—C20122.0 (8)
N2—C8—H8117.7N4—C21—H21119.0
C7—C8—H8117.7C20—C21—H21119.0
N2—C9—C5125.0 (7)N4—C22—C18123.4 (8)
N2—C9—C1117.0 (6)N4—C22—C14117.3 (7)
C5—C9—C1117.9 (6)C18—C22—C14119.2 (7)
C11—C10—S2115.5 (6)C24—C23—S4122.0 (5)
C11—C10—S1121.4 (6)C24—C23—S3118.4 (5)
S2—C10—S1123.1 (5)S4—C23—S3119.6 (5)
C10—C11—C12106.4 (6)C23—C24—C2595.1 (5)
C10—C11—H11126.8C23—C24—H24132.5
C12—C11—H11126.8C25—C24—H24132.5
C13—C12—C11112.2 (6)C26—C25—C24119.2 (6)
C13—C12—Br1126.2 (6)C26—C25—Br3123.2 (5)
C11—C12—Br1121.6 (5)C24—C25—Br3117.5 (5)
C12—C13—S2115.2 (6)C25—C26—S4115.1 (6)
C12—C13—Br2125.0 (6)C25—C26—Br4128.1 (5)
S2—C13—Br2119.6 (5)S4—C26—Br4116.8 (4)
O1—S1—N1—C154.0 (6)O4—S3—N3—C1456.0 (7)
O2—S1—N1—C1174.1 (5)O3—S3—N3—C14172.7 (6)
C10—S1—N1—C159.7 (6)C23—S3—N3—C1460.3 (7)
S1—N1—C1—C240.8 (10)S3—N3—C14—C1542.4 (10)
S1—N1—C1—C9140.1 (5)S3—N3—C14—C22139.4 (6)
N1—C1—C2—C3178.6 (6)N3—C14—C15—C16178.4 (7)
C9—C1—C2—C32.3 (11)C22—C14—C15—C160.3 (12)
C1—C2—C3—C41.4 (13)C14—C15—C16—C171.8 (14)
C2—C3—C4—C51.0 (12)C15—C16—C17—C181.1 (13)
C3—C4—C5—C92.4 (11)C16—C17—C18—C221.7 (11)
C3—C4—C5—C6178.2 (7)C16—C17—C18—C19179.1 (7)
C9—C5—C6—C71.7 (10)C22—C18—C19—C201.1 (10)
C4—C5—C6—C7177.6 (7)C17—C18—C19—C20178.1 (7)
C5—C6—C7—C81.5 (11)C18—C19—C20—C212.5 (11)
C9—N2—C8—C72.6 (11)C22—N4—C21—C200.4 (10)
C6—C7—C8—N23.9 (12)C19—C20—C21—N42.2 (12)
C8—N2—C9—C51.0 (10)C21—N4—C22—C181.1 (10)
C8—N2—C9—C1179.7 (6)C21—N4—C22—C14177.5 (6)
C6—C5—C9—N23.1 (10)C17—C18—C22—N4179.9 (7)
C4—C5—C9—N2179.3 (7)C19—C18—C22—N40.7 (11)
C6—C5—C9—C1177.6 (6)C17—C18—C22—C143.8 (10)
C4—C5—C9—C11.4 (9)C19—C18—C22—C14177.0 (6)
C2—C1—C9—N2178.5 (7)C15—C14—C22—N4179.6 (7)
N1—C1—C9—N20.7 (8)N3—C14—C22—N42.1 (9)
C2—C1—C9—C50.9 (10)C15—C14—C22—C183.0 (10)
N1—C1—C9—C5179.9 (6)N3—C14—C22—C18178.6 (6)
C13—S2—C10—C110.3 (5)C26—S4—C23—C240.6 (6)
C13—S2—C10—S1179.6 (5)C26—S4—C23—S3179.5 (5)
O1—S1—C10—C11148.7 (6)O4—S3—C23—C24144.6 (6)
O2—S1—C10—C1116.7 (6)O3—S3—C23—C2413.4 (7)
N1—S1—C10—C1196.5 (6)N3—S3—C23—C2498.8 (6)
O1—S1—C10—S232.1 (5)O4—S3—C23—S435.3 (6)
O2—S1—C10—S2164.0 (4)O3—S3—C23—S4166.5 (5)
N1—S1—C10—S282.8 (5)N3—S3—C23—S481.3 (6)
S2—C10—C11—C120.1 (7)S4—C23—C24—C251.7 (7)
S1—C10—C11—C12179.2 (5)S3—C23—C24—C25178.4 (5)
C10—C11—C12—C130.7 (8)C23—C24—C25—C262.6 (8)
C10—C11—C12—Br1179.2 (5)C23—C24—C25—Br3179.5 (5)
C11—C12—C13—S21.0 (8)C24—C25—C26—S42.7 (9)
Br1—C12—C13—S2178.8 (4)Br3—C25—C26—S4179.4 (4)
C11—C12—C13—Br2175.8 (5)C24—C25—C26—Br4176.9 (5)
Br1—C12—C13—Br24.0 (10)Br3—C25—C26—Br40.2 (10)
C10—S2—C13—C120.8 (6)C23—S4—C26—C251.2 (6)
C10—S2—C13—Br2175.9 (4)C23—S4—C26—Br4178.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.513.215 (9)133
C20—H20···O3ii0.932.603.253 (10)127
Symmetry codes: (i) x, y+1, z1/2; (ii) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H8Br2N2O2S2
Mr448.15
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)299
a, b, c (Å)28.318 (2), 7.0471 (5), 15.094 (1)
V3)3012.2 (4)
Z8
Radiation typeMo Kα
µ (mm1)5.66
Crystal size (mm)0.28 × 0.10 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur (TM)
diffractometer with Sapphire CCD detector
Absorption correctionAnalytical
(CrysAlis RED-CCD; Oxford Diffraction, 2004)
Tmin, Tmax0.344, 0.760
No. of measured, independent and
observed [I > 2σ(I)] reflections
20485, 6068, 3494
Rint0.063
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.103, 0.88
No. of reflections6068
No. of parameters380
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.69, 0.54
Absolute structureFlack (1983)
Absolute structure parameter0.00 (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.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.513.215 (9)133
C20—H20···O3ii0.932.603.253 (10)127
Symmetry codes: (i) x, y+1, z1/2; (ii) x+1/2, y+1/2, z+1/2.
 

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