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The title compound, C16H6Br2Cl2N2S2, was synthesized from the reaction of equimolar amounts of 1,2-diamino-4,5-dichloro­benzene and 1,2-bis­(5-bromo­thien-2­yl)ethanedione. The crystal structure was determined at 100 K.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006793/lh6378sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006793/lh6378Isup2.hkl
Contains datablock I

CCDC reference: 270479

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.031
  • wR factor = 0.067
  • Data-to-parameter ratio = 24.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Br2 .. N1 .. 3.09 Ang.
Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C16 H6 Br2 Cl2 N2 S2
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 30.56 From the CIF: _reflns_number_total 5351 Count of symmetry unique reflns 2981 Completeness (_total/calc) 179.50% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2370 Fraction of Friedel pairs measured 0.795 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

2,3-Bis(5-bromothien-2-yl)-6,7-dichloroquinoxaline top
Crystal data top
C16H6Br2Cl2N2S2Dx = 1.982 Mg m3
Mr = 521.07Melting point: 448 K
Tetragonal, P421cMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -4 2nCell parameters from 6538 reflections
a = 20.2456 (6) Åθ = 2.6–30.3°
c = 8.5209 (5) ŵ = 5.19 mm1
V = 3492.6 (3) Å3T = 100 K
Z = 8Needle, yellow
F(000) = 20160.19 × 0.05 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer
5351 independent reflections
Radiation source: fine-focus sealed tube4694 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ω scansθmax = 30.6°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2828
Tmin = 0.667, Tmax = 0.77k = 2828
41333 measured reflectionsl = 1212
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)] = 0.031H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0368P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.012
5351 reflectionsΔρmax = 0.65 e Å3
217 parametersΔρmin = 0.33 e Å3
0 restraintsAbsolute structure: Flack (1983), 2370 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.001 (6)
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
Br11.048010 (14)0.080531 (15)0.18415 (5)0.02521 (8)
S10.91715 (4)0.09516 (4)0.37264 (9)0.01759 (14)
Cl10.64125 (4)0.02239 (4)0.88776 (9)0.02249 (15)
N10.78424 (12)0.10268 (11)0.5012 (3)0.0146 (5)
C10.79825 (14)0.15682 (13)0.4197 (3)0.0141 (5)
Br20.727628 (14)0.471188 (13)0.17945 (4)0.01992 (7)
S20.70720 (3)0.32782 (3)0.29891 (9)0.01427 (13)
Cl20.53316 (3)0.08809 (4)0.84613 (8)0.02127 (15)
N20.69738 (12)0.21098 (11)0.5013 (3)0.0145 (5)
C20.75511 (13)0.21390 (14)0.4294 (3)0.0133 (5)
C30.68172 (14)0.15410 (13)0.5803 (3)0.0139 (5)
C40.62121 (13)0.14944 (14)0.6601 (3)0.0155 (5)
H4A0.58960.18390.65180.019*
C50.60810 (13)0.09508 (14)0.7499 (3)0.0154 (5)
C60.65554 (15)0.04401 (13)0.7644 (3)0.0165 (6)
C70.71394 (13)0.04698 (13)0.6834 (4)0.0168 (5)
H7A0.74510.01210.69250.020*
C80.72774 (14)0.10150 (13)0.5872 (3)0.0140 (5)
C90.85771 (13)0.15373 (13)0.3239 (4)0.0145 (5)
C100.87631 (14)0.18765 (13)0.1902 (4)0.0162 (5)
H10A0.84990.22110.14340.019*
C110.93785 (15)0.16806 (15)0.1300 (3)0.0183 (6)
H11A0.95780.18670.03920.022*
C120.96524 (14)0.11942 (14)0.2172 (3)0.0171 (6)
C130.77147 (14)0.27928 (14)0.3668 (3)0.0149 (5)
C140.82989 (14)0.31374 (14)0.3661 (3)0.0160 (6)
H14A0.87060.29570.40130.019*
C150.82344 (14)0.37879 (13)0.3078 (4)0.0176 (5)
H15A0.85900.40920.29880.021*
C160.76003 (15)0.39244 (14)0.2663 (3)0.0166 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01469 (13)0.02736 (16)0.03358 (16)0.00173 (11)0.00361 (13)0.00505 (15)
S10.0164 (3)0.0152 (3)0.0211 (3)0.0031 (3)0.0018 (3)0.0019 (3)
Cl10.0256 (4)0.0161 (3)0.0257 (4)0.0000 (3)0.0040 (3)0.0064 (3)
N10.0153 (11)0.0130 (11)0.0156 (12)0.0003 (9)0.0008 (9)0.0020 (9)
C10.0165 (13)0.0122 (12)0.0135 (13)0.0002 (10)0.0018 (10)0.0016 (10)
Br20.02237 (14)0.01332 (12)0.02407 (14)0.00045 (10)0.00158 (13)0.00474 (12)
S20.0146 (3)0.0119 (3)0.0163 (3)0.0007 (2)0.0014 (3)0.0010 (3)
Cl20.0160 (3)0.0223 (3)0.0255 (4)0.0009 (3)0.0035 (3)0.0035 (3)
N20.0143 (11)0.0118 (11)0.0175 (12)0.0016 (9)0.0036 (9)0.0003 (9)
C20.0129 (12)0.0142 (13)0.0127 (13)0.0005 (10)0.0040 (10)0.0022 (10)
C30.0150 (13)0.0113 (12)0.0154 (13)0.0008 (10)0.0026 (11)0.0020 (10)
C40.0141 (12)0.0159 (12)0.0165 (14)0.0008 (10)0.0023 (10)0.0014 (11)
C50.0118 (12)0.0157 (13)0.0185 (13)0.0026 (10)0.0008 (10)0.0011 (11)
C60.0209 (14)0.0131 (13)0.0155 (13)0.0014 (11)0.0011 (11)0.0014 (10)
C70.0175 (13)0.0139 (12)0.0189 (13)0.0018 (10)0.0042 (12)0.0010 (12)
C80.0133 (12)0.0138 (13)0.0149 (13)0.0009 (10)0.0013 (10)0.0031 (10)
C90.0142 (12)0.0130 (12)0.0162 (12)0.0009 (10)0.0020 (12)0.0035 (11)
C100.0208 (13)0.0167 (13)0.0111 (13)0.0024 (10)0.0003 (12)0.0019 (11)
C110.0206 (14)0.0195 (14)0.0147 (13)0.0018 (11)0.0034 (11)0.0030 (11)
C120.0125 (12)0.0181 (13)0.0206 (15)0.0002 (10)0.0012 (11)0.0065 (11)
C130.0167 (13)0.0135 (13)0.0144 (12)0.0043 (10)0.0021 (10)0.0010 (10)
C140.0151 (13)0.0151 (13)0.0179 (14)0.0011 (11)0.0011 (11)0.0025 (10)
C150.0174 (12)0.0158 (12)0.0196 (14)0.0023 (10)0.0024 (12)0.0012 (12)
C160.0227 (15)0.0102 (12)0.0169 (13)0.0001 (11)0.0001 (11)0.0009 (10)
Geometric parameters (Å, º) top
Br1—C121.873 (3)C4—C51.366 (4)
S1—C121.716 (3)C4—H4A0.9500
S1—C91.740 (3)C5—C61.417 (4)
Cl1—C61.731 (3)C6—C71.370 (4)
N1—C11.328 (4)C7—C81.403 (4)
N1—C81.359 (4)C7—H7A0.9500
C1—C21.451 (4)C9—C101.382 (4)
C1—C91.456 (4)C10—C111.405 (4)
Br2—C161.876 (3)C10—H10A0.9500
S2—C161.712 (3)C11—C121.353 (4)
S2—C131.730 (3)C11—H11A0.9500
Cl2—C51.730 (3)C13—C141.373 (4)
N2—C21.321 (4)C14—C151.413 (4)
N2—C31.371 (3)C14—H14A0.9500
C2—C131.465 (4)C15—C161.360 (4)
C3—C41.404 (4)C15—H15A0.9500
C3—C81.416 (4)
C12—S1—C990.75 (14)N1—C8—C3121.2 (3)
C1—N1—C8118.4 (2)C7—C8—C3119.0 (3)
N1—C1—C2119.9 (3)C10—C9—C1131.8 (3)
N1—C1—C9115.7 (2)C10—C9—S1110.3 (2)
C2—C1—C9124.3 (2)C1—C9—S1117.9 (2)
C16—S2—C1391.06 (14)C9—C10—C11113.7 (3)
C2—N2—C3118.0 (2)C9—C10—H10A123.1
N2—C2—C1121.6 (3)C11—C10—H10A123.1
N2—C2—C13114.2 (2)C12—C11—C10111.6 (3)
C1—C2—C13124.2 (2)C12—C11—H11A124.2
N2—C3—C4119.7 (2)C10—C11—H11A124.2
N2—C3—C8120.0 (3)C11—C12—S1113.6 (2)
C4—C3—C8120.2 (3)C11—C12—Br1126.2 (2)
C5—C4—C3119.7 (3)S1—C12—Br1120.23 (17)
C5—C4—H4A120.2C14—C13—C2130.9 (3)
C3—C4—H4A120.2C14—C13—S2111.0 (2)
C4—C5—C6120.3 (3)C2—C13—S2117.7 (2)
C4—C5—Cl2120.1 (2)C13—C14—C15113.3 (3)
C6—C5—Cl2119.6 (2)C13—C14—H14A123.4
C7—C6—C5120.6 (3)C15—C14—H14A123.4
C7—C6—Cl1119.0 (2)C16—C15—C14111.6 (2)
C5—C6—Cl1120.4 (2)C16—C15—H15A124.2
C6—C7—C8120.0 (3)C14—C15—H15A124.2
C6—C7—H7A120.0C15—C16—S2113.1 (2)
C8—C7—H7A120.0C15—C16—Br2127.3 (2)
N1—C8—C7119.8 (3)S2—C16—Br2119.66 (17)
C8—N1—C1—C22.7 (4)C4—C3—C8—C74.4 (4)
C8—N1—C1—C9177.0 (2)N1—C1—C9—C10155.1 (3)
C3—N2—C2—C16.2 (4)C2—C1—C9—C1024.5 (5)
C3—N2—C2—C13172.0 (2)N1—C1—C9—S121.2 (3)
N1—C1—C2—N28.9 (4)C2—C1—C9—S1159.1 (2)
C9—C1—C2—N2170.8 (3)C12—S1—C9—C101.5 (2)
N1—C1—C2—C13169.1 (3)C12—S1—C9—C1178.6 (2)
C9—C1—C2—C1311.2 (4)C1—C9—C10—C11177.9 (3)
C2—N2—C3—C4179.1 (2)S1—C9—C10—C111.4 (3)
C2—N2—C3—C82.0 (4)C9—C10—C11—C120.4 (4)
N2—C3—C4—C5174.4 (2)C10—C11—C12—S10.8 (3)
C8—C3—C4—C52.7 (4)C10—C11—C12—Br1177.8 (2)
C3—C4—C5—C60.9 (4)C9—S1—C12—C111.4 (2)
C3—C4—C5—Cl2178.9 (2)C9—S1—C12—Br1177.34 (17)
C4—C5—C6—C72.9 (4)N2—C2—C13—C14138.8 (3)
Cl2—C5—C6—C7176.9 (2)C1—C2—C13—C1439.4 (5)
C4—C5—C6—Cl1175.9 (2)N2—C2—C13—S233.3 (3)
Cl2—C5—C6—Cl14.3 (3)C1—C2—C13—S2148.6 (2)
C5—C6—C7—C81.1 (4)C16—S2—C13—C141.4 (2)
Cl1—C6—C7—C8177.6 (2)C16—S2—C13—C2175.0 (2)
C1—N1—C8—C7175.4 (3)C2—C13—C14—C15173.8 (3)
C1—N1—C8—C35.4 (4)S2—C13—C14—C151.3 (3)
C6—C7—C8—N1176.8 (3)C13—C14—C15—C160.4 (4)
C6—C7—C8—C32.5 (4)C14—C15—C16—S20.8 (3)
N2—C3—C8—N18.1 (4)C14—C15—C16—Br2178.6 (2)
C4—C3—C8—N1174.8 (3)C13—S2—C16—C151.3 (2)
N2—C3—C8—C7172.7 (3)C13—S2—C16—Br2178.12 (18)
 

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