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In the title compound, C21H10Br2F4N2O4S, the quinoline ring system, carrying two Br atoms, is essentially planar. The torsion angles about the N—S bonds connecting the quinoline ring to the aromatic rings are 84.0 (3) and 120.8 (3)°. Inter­molecular C—H...O hydrogen bonds link mol­ecules into a three-dimensional array.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020381/tk2045sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020381/tk2045Isup2.hkl
Contains datablock I

CCDC reference: 613830

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.044
  • wR factor = 0.122
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.11 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT431_ALERT_2_C Short Inter HL..A Contact F2 .. O1 .. 2.93 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.108 Tmax scaled 0.505 Tmin scaled 0.208
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); 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.

N-(5,7-Dibromo-8-quinolyl)-3,5-difluorobenzenesulfonamide top
Crystal data top
C21H10Br2F4N2O4S2F(000) = 1280
Mr = 654.25Dx = 1.903 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 9.758 (1) Åθ = 5.8–20.5°
b = 24.091 (2) ŵ = 6.83 mm1
c = 9.851 (1) ÅT = 299 K
β = 99.56 (1)°Prism, light pink
V = 2283.6 (4) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
3269 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
Graphite monochromatorθmax = 66.9°, θmin = 3.7°
ω/2θ scansh = 111
Absorption correction: ψ scan
(North et al., 1968)
k = 028
Tmin = 0.188, Tmax = 0.456l = 1111
4450 measured reflections3 standard reflections every 120 min
4057 independent reflections intensity decay: 1.0%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0603P)2 + 3.291P]
where P = (Fo2 + 2Fc2)/3
4057 reflections(Δ/σ)max = 0.001
316 parametersΔρmax = 0.73 e Å3
0 restraintsΔρmin = 0.93 e Å3
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
C10.4927 (4)0.13178 (17)0.7813 (4)0.0413 (9)
C20.4062 (4)0.17712 (17)0.7653 (4)0.0460 (9)
C30.2722 (5)0.1737 (2)0.6877 (5)0.0528 (11)
H30.21440.20470.67790.063*
C40.2278 (5)0.1252 (2)0.6273 (4)0.0513 (10)
C50.3110 (4)0.07669 (19)0.6400 (4)0.0474 (10)
C60.2715 (6)0.0246 (2)0.5808 (5)0.0602 (12)
H60.18530.02050.52500.072*
C70.3584 (6)0.0194 (2)0.6047 (5)0.0676 (14)
H70.33350.05400.56610.081*
C80.4891 (6)0.0110 (2)0.6909 (5)0.0600 (12)
H80.54810.04150.70820.072*
C90.4448 (4)0.08058 (17)0.7213 (4)0.0443 (9)
C100.7677 (4)0.21637 (17)0.7299 (4)0.0450 (9)
C110.8431 (5)0.25050 (18)0.8284 (5)0.0546 (11)
H110.88950.23650.91140.065*
C120.8459 (5)0.3063 (2)0.7973 (5)0.0586 (12)
C130.7786 (5)0.3287 (2)0.6790 (6)0.0648 (14)
H130.78090.36670.66250.078*
C140.7067 (5)0.2931 (2)0.5844 (6)0.0634 (14)
C150.6986 (5)0.2362 (2)0.6063 (5)0.0540 (11)
H150.64900.21280.54070.065*
C160.7750 (4)0.07706 (17)1.0751 (4)0.0448 (9)
C170.7254 (5)0.02423 (18)1.0442 (5)0.0519 (10)
H170.63580.01820.99750.062*
C180.8139 (6)0.01898 (18)1.0854 (5)0.0572 (12)
C190.9450 (6)0.0125 (2)1.1547 (5)0.0609 (13)
H191.00200.04281.18230.073*
C200.9896 (5)0.0411 (2)1.1823 (5)0.0560 (11)
C210.9081 (5)0.08725 (19)1.1448 (4)0.0510 (10)
H210.94070.12311.16500.061*
N10.6334 (3)0.13586 (13)0.8532 (3)0.0409 (7)
N20.5315 (4)0.03532 (15)0.7463 (4)0.0527 (9)
O10.8845 (3)0.12885 (12)0.8493 (3)0.0529 (8)
O20.7174 (4)0.11836 (13)0.6324 (3)0.0564 (8)
O30.7397 (4)0.18316 (12)1.0750 (3)0.0624 (9)
O40.5330 (4)0.12307 (15)1.0642 (4)0.0631 (9)
F10.9212 (4)0.34060 (13)0.8914 (4)0.0928 (11)
F20.6422 (4)0.31312 (16)0.4628 (4)0.1037 (13)
F30.7680 (4)0.07141 (11)1.0545 (4)0.0874 (10)
F41.1214 (3)0.04933 (15)1.2467 (3)0.0830 (9)
Br10.45869 (5)0.245713 (19)0.85132 (6)0.05850 (17)
Br20.04437 (6)0.12241 (3)0.52693 (6)0.0762 (2)
S10.76056 (11)0.14484 (4)0.76097 (11)0.0430 (2)
S20.66461 (12)0.13452 (4)1.02820 (11)0.0474 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.042 (2)0.044 (2)0.038 (2)0.0022 (17)0.0061 (17)0.0022 (17)
C20.049 (2)0.040 (2)0.050 (2)0.0039 (18)0.0107 (19)0.0007 (18)
C30.049 (2)0.058 (3)0.049 (2)0.009 (2)0.004 (2)0.004 (2)
C40.044 (2)0.067 (3)0.042 (2)0.001 (2)0.0053 (18)0.004 (2)
C50.047 (2)0.058 (3)0.038 (2)0.006 (2)0.0089 (17)0.0011 (19)
C60.068 (3)0.064 (3)0.047 (3)0.019 (3)0.006 (2)0.007 (2)
C70.094 (4)0.054 (3)0.055 (3)0.016 (3)0.015 (3)0.014 (2)
C80.082 (3)0.045 (2)0.055 (3)0.008 (2)0.017 (2)0.004 (2)
C90.051 (2)0.042 (2)0.041 (2)0.0002 (18)0.0102 (18)0.0033 (17)
C100.045 (2)0.039 (2)0.052 (2)0.0020 (17)0.0104 (19)0.0067 (18)
C110.058 (3)0.047 (2)0.058 (3)0.001 (2)0.007 (2)0.006 (2)
C120.064 (3)0.048 (2)0.065 (3)0.008 (2)0.014 (2)0.000 (2)
C130.062 (3)0.044 (2)0.090 (4)0.003 (2)0.020 (3)0.015 (3)
C140.053 (3)0.062 (3)0.076 (3)0.008 (2)0.013 (2)0.034 (3)
C150.052 (3)0.053 (2)0.055 (3)0.002 (2)0.004 (2)0.012 (2)
C160.053 (2)0.041 (2)0.040 (2)0.0064 (18)0.0062 (18)0.0043 (17)
C170.065 (3)0.048 (2)0.043 (2)0.004 (2)0.009 (2)0.0031 (19)
C180.088 (4)0.039 (2)0.048 (3)0.002 (2)0.022 (2)0.0013 (19)
C190.086 (4)0.050 (3)0.049 (3)0.022 (3)0.019 (3)0.012 (2)
C200.057 (3)0.066 (3)0.045 (2)0.013 (2)0.006 (2)0.009 (2)
C210.057 (3)0.049 (2)0.045 (2)0.003 (2)0.003 (2)0.0022 (19)
N10.0428 (18)0.0380 (17)0.0415 (18)0.0021 (14)0.0058 (14)0.0011 (14)
N20.059 (2)0.046 (2)0.053 (2)0.0017 (17)0.0089 (17)0.0017 (17)
O10.0438 (16)0.0439 (16)0.070 (2)0.0090 (13)0.0064 (14)0.0096 (14)
O20.066 (2)0.0526 (17)0.0540 (18)0.0068 (15)0.0198 (15)0.0116 (14)
O30.079 (2)0.0428 (16)0.058 (2)0.0075 (16)0.0094 (17)0.0116 (14)
O40.0563 (19)0.081 (2)0.0554 (19)0.0178 (17)0.0200 (15)0.0054 (17)
F10.124 (3)0.0536 (17)0.098 (3)0.0306 (18)0.010 (2)0.0098 (17)
F20.100 (3)0.093 (2)0.105 (3)0.010 (2)0.023 (2)0.059 (2)
F30.140 (3)0.0390 (14)0.084 (2)0.0034 (17)0.022 (2)0.0021 (14)
F40.0626 (18)0.097 (2)0.083 (2)0.0171 (17)0.0063 (16)0.0157 (18)
Br10.0614 (3)0.0415 (3)0.0715 (3)0.0091 (2)0.0076 (2)0.0045 (2)
Br20.0520 (3)0.0997 (5)0.0712 (4)0.0011 (3)0.0066 (3)0.0009 (3)
S10.0436 (5)0.0362 (5)0.0497 (6)0.0033 (4)0.0090 (4)0.0004 (4)
S20.0540 (6)0.0433 (5)0.0437 (5)0.0096 (4)0.0047 (5)0.0029 (4)
Geometric parameters (Å, º) top
C1—C21.373 (6)C12—F11.363 (6)
C1—C91.413 (6)C13—C141.371 (8)
C1—N11.440 (5)C13—H130.9300
C2—C31.403 (6)C14—F21.347 (6)
C2—Br11.889 (4)C14—C151.391 (7)
C3—C41.351 (7)C15—H150.9300
C3—H30.9300C16—C171.378 (6)
C4—C51.416 (6)C16—C211.387 (6)
C4—Br21.897 (4)C16—S21.768 (4)
C5—C61.410 (6)C17—C181.370 (7)
C5—C91.417 (6)C17—H170.9300
C6—C71.354 (7)C18—C191.356 (8)
C6—H60.9300C18—F31.358 (5)
C7—C81.425 (8)C19—C201.375 (7)
C7—H70.9300C19—H190.9300
C8—N21.281 (6)C20—F41.351 (6)
C8—H80.9300C20—C211.381 (6)
C9—N21.377 (5)C21—H210.9300
C10—C151.376 (6)N1—S11.670 (4)
C10—C111.386 (6)N1—S21.700 (3)
C10—S11.754 (4)O1—S11.421 (3)
C11—C121.379 (6)O2—S11.418 (3)
C11—H110.9300O3—S21.418 (3)
C12—C131.352 (7)O4—S21.415 (4)
C2—C1—C9119.5 (4)F2—C14—C15117.4 (5)
C2—C1—N1121.3 (4)C13—C14—C15123.2 (5)
C9—C1—N1119.2 (3)C10—C15—C14116.6 (5)
C1—C2—C3121.0 (4)C10—C15—H15121.7
C1—C2—Br1121.9 (3)C14—C15—H15121.7
C3—C2—Br1117.0 (3)C17—C16—C21122.6 (4)
C4—C3—C2119.5 (4)C17—C16—S2119.3 (3)
C4—C3—H3120.3C21—C16—S2118.1 (3)
C2—C3—H3120.3C18—C17—C16117.1 (4)
C3—C4—C5122.6 (4)C18—C17—H17121.5
C3—C4—Br2117.7 (4)C16—C17—H17121.5
C5—C4—Br2119.6 (3)C19—C18—F3118.0 (4)
C6—C5—C4125.7 (4)C19—C18—C17123.9 (4)
C6—C5—C9117.1 (4)F3—C18—C17118.1 (5)
C4—C5—C9117.1 (4)C18—C19—C20116.7 (4)
C7—C6—C5120.3 (5)C18—C19—H19121.7
C7—C6—H6119.8C20—C19—H19121.7
C5—C6—H6119.8F4—C20—C19118.4 (4)
C6—C7—C8117.7 (4)F4—C20—C21117.9 (5)
C6—C7—H7121.1C19—C20—C21123.6 (5)
C8—C7—H7121.1C20—C21—C16116.1 (4)
N2—C8—C7124.8 (5)C20—C21—H21121.9
N2—C8—H8117.6C16—C21—H21121.9
C7—C8—H8117.6C1—N1—S1118.4 (3)
N2—C9—C1117.8 (4)C1—N1—S2119.6 (3)
N2—C9—C5122.0 (4)S1—N1—S2122.0 (2)
C1—C9—C5120.3 (4)C8—N2—C9118.0 (4)
C15—C10—C11122.6 (4)O2—S1—O1121.4 (2)
C15—C10—S1117.9 (3)O2—S1—N1106.91 (19)
C11—C10—S1119.5 (3)O1—S1—N1105.40 (18)
C12—C11—C10116.8 (4)O2—S1—C10107.5 (2)
C12—C11—H11121.6O1—S1—C10108.61 (19)
C10—C11—H11121.6N1—S1—C10106.07 (18)
C13—C12—F1118.2 (4)O4—S2—O3121.4 (2)
C13—C12—C11123.8 (5)O4—S2—N1103.91 (19)
F1—C12—C11118.0 (5)O3—S2—N1108.05 (19)
C12—C13—C14117.1 (5)O4—S2—C16108.7 (2)
C12—C13—H13121.4O3—S2—C16107.6 (2)
C14—C13—H13121.4N1—S2—C16106.18 (18)
F2—C14—C13119.4 (5)
C9—C1—C2—C31.4 (6)F3—C18—C19—C20178.8 (4)
N1—C1—C2—C3175.9 (4)C17—C18—C19—C200.9 (7)
C9—C1—C2—Br1176.2 (3)C18—C19—C20—F4177.6 (4)
N1—C1—C2—Br16.5 (6)C18—C19—C20—C210.7 (7)
C1—C2—C3—C40.3 (7)F4—C20—C21—C16178.0 (4)
Br1—C2—C3—C4178.0 (3)C19—C20—C21—C160.3 (7)
C2—C3—C4—C50.6 (7)C17—C16—C21—C200.1 (7)
C2—C3—C4—Br2178.7 (3)S2—C16—C21—C20178.5 (3)
C3—C4—C5—C6179.6 (4)C2—C1—N1—S196.5 (4)
Br2—C4—C5—C61.6 (6)C9—C1—N1—S180.8 (4)
C3—C4—C5—C90.8 (7)C2—C1—N1—S280.6 (4)
Br2—C4—C5—C9177.2 (3)C9—C1—N1—S2102.0 (4)
C4—C5—C6—C7177.4 (5)C7—C8—N2—C90.1 (7)
C9—C5—C6—C71.4 (7)C1—C9—N2—C8179.3 (4)
C5—C6—C7—C80.1 (7)C5—C9—N2—C81.5 (6)
C6—C7—C8—N20.9 (8)C1—N1—S1—O230.5 (3)
C2—C1—C9—N2176.4 (4)S2—N1—S1—O2152.5 (2)
N1—C1—C9—N26.3 (6)C1—N1—S1—O1160.9 (3)
C2—C1—C9—C52.9 (6)S2—N1—S1—O122.0 (3)
N1—C1—C9—C5174.5 (4)C1—N1—S1—C1084.0 (3)
C6—C5—C9—N22.3 (6)S2—N1—S1—C1093.1 (3)
C4—C5—C9—N2176.7 (4)C15—C10—S1—O217.5 (4)
C6—C5—C9—C1178.6 (4)C11—C10—S1—O2161.7 (4)
C4—C5—C9—C12.5 (6)C15—C10—S1—O1150.5 (4)
C15—C10—C11—C120.2 (7)C11—C10—S1—O128.7 (4)
S1—C10—C11—C12179.3 (4)C15—C10—S1—N196.6 (4)
C10—C11—C12—C130.9 (8)C11—C10—S1—N184.2 (4)
C10—C11—C12—F1178.9 (4)C1—N1—S2—O46.2 (3)
F1—C12—C13—C14178.2 (5)S1—N1—S2—O4176.8 (2)
C11—C12—C13—C141.6 (8)C1—N1—S2—O3124.0 (3)
C12—C13—C14—F2177.6 (5)S1—N1—S2—O353.0 (3)
C12—C13—C14—C151.2 (8)C1—N1—S2—C16120.8 (3)
C11—C10—C15—C140.6 (7)S1—N1—S2—C1662.2 (3)
S1—C10—C15—C14179.7 (4)C17—C16—S2—O445.2 (4)
F2—C14—C15—C10178.6 (4)C21—C16—S2—O4133.4 (4)
C13—C14—C15—C100.2 (7)C17—C16—S2—O3178.4 (4)
C21—C16—C17—C180.1 (7)C21—C16—S2—O30.2 (4)
S2—C16—C17—C18178.6 (3)C17—C16—S2—N166.1 (4)
C16—C17—C18—C190.5 (7)C21—C16—S2—N1115.4 (4)
C16—C17—C18—F3179.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O1i0.932.403.264 (5)155
C7—H7···O2ii0.932.483.333 (6)152
Symmetry codes: (i) x+2, y, z+2; (ii) x+1, y, z+1.
 

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