4-Bromo-N-(8-quinolyl)benzene­sulfonamide

In the title compound, C₁₅H₁₁BrN₂O₂S, the torsion angle about the central C-N-S-C bridge is 55.1 (5)°. The dihedral angle between the planes of the nearly planar quinoline group and the bromo­benzene ring is 72.0 (1)°. No classical hydrogen bonds were found in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.105
• wR factor = 0.273
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.15
            Rint given   0.177
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 .........       0.18

Alert level C
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.105
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.273
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.79
PLAT084_ALERT_2_C High R2 Value ..................................       0.27
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

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      0.787
            Tmax scaled      0.387 Tmin scaled      0.220

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 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
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC; 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.

4-Bromo-N-8-quinolylbenzenesulfonamide

Crystal data

C15H11BrN2O2S	F(000) = 728
Mr = 363.23	Dx = 1.667 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 6.780 (1) Å	θ = 4.3–20.2°
b = 14.253 (3) Å	µ = 5.27 mm^−1
c = 15.232 (4) Å	T = 299 K
β = 100.43 (2)°	Thick needle, colourless
V = 1447.6 (5) Å^3	0.40 × 0.20 × 0.18 mm
Z = 4

Data collection

Nonius CAD-4 diffractometer	2101 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.177
Graphite monochromator	θmax = 66.9°, θmin = 4.3°
ω/2θ scans	h = −7→0
Absorption correction: ψ scan (North et al., 1968)	k = −17→2
Tmin = 0.280, Tmax = 0.492	l = −17→18
3102 measured reflections	3 standard reflections every 120 min
2534 independent reflections	intensity decay: −20%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.105	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.273	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
2534 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 1.65 e Å^−3
0 restraints	Δρmin = −1.39 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	1.03185 (14)	0.50453 (5)	0.65239 (7)	0.0795 (5)
S1	0.4350 (2)	0.20470 (8)	0.43491 (9)	0.0411 (5)
O1	0.2400 (7)	0.2122 (3)	0.4587 (3)	0.0582 (12)
O2	0.5314 (8)	0.1161 (3)	0.4392 (3)	0.0594 (12)
N1	0.4041 (7)	0.2440 (3)	0.3319 (3)	0.0448 (11)
H1N	0.2837	0.2542	0.3043	0.054*
N2	0.3709 (7)	0.3939 (3)	0.2275 (4)	0.0495 (12)
C1	0.5637 (8)	0.2619 (4)	0.2857 (4)	0.0378 (11)
C2	0.7293 (9)	0.2059 (4)	0.2910 (4)	0.0478 (13)
H2	0.7432	0.1527	0.3268	0.057*
C3	0.8783 (9)	0.2299 (5)	0.2416 (4)	0.0533 (15)
H3	0.9911	0.1919	0.2455	0.064*
C4	0.8624 (9)	0.3066 (5)	0.1884 (4)	0.0513 (15)
H4	0.9641	0.3213	0.1572	0.062*
C5	0.6895 (8)	0.3644 (4)	0.1805 (4)	0.0443 (12)
C6	0.6570 (11)	0.4433 (4)	0.1250 (4)	0.0544 (15)
H6	0.7519	0.4607	0.0909	0.065*
C7	0.4861 (13)	0.4942 (4)	0.1210 (5)	0.0612 (18)
H7	0.4623	0.5459	0.0833	0.073*
C8	0.3440 (11)	0.4683 (5)	0.1746 (5)	0.0604 (17)
H8	0.2290	0.5044	0.1724	0.072*
C9	0.5428 (7)	0.3423 (3)	0.2306 (4)	0.0382 (11)
C10	0.6004 (8)	0.2839 (3)	0.5002 (4)	0.0374 (11)
C11	0.8041 (8)	0.2663 (4)	0.5169 (4)	0.0414 (12)
H11	0.8541	0.2107	0.4975	0.050*
C12	0.9323 (9)	0.3320 (4)	0.5626 (4)	0.0492 (14)
H12	1.0701	0.3220	0.5730	0.059*
C13	0.8548 (9)	0.4126 (4)	0.5929 (4)	0.0460 (12)
C14	0.6489 (10)	0.4282 (4)	0.5797 (5)	0.0562 (16)
H14	0.5984	0.4819	0.6024	0.067*
C15	0.5229 (9)	0.3646 (4)	0.5336 (5)	0.0501 (13)
H15	0.3851	0.3745	0.5242	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0808 (7)	0.0641 (6)	0.0859 (8)	−0.0245 (4)	−0.0056 (5)	−0.0214 (4)
S1	0.0389 (8)	0.0367 (7)	0.0478 (8)	−0.0074 (4)	0.0084 (6)	0.0032 (5)
O1	0.036 (2)	0.072 (3)	0.069 (3)	−0.0179 (18)	0.019 (2)	0.000 (2)
O2	0.074 (3)	0.0288 (18)	0.071 (3)	−0.0029 (17)	0.002 (2)	0.0040 (17)
N1	0.032 (2)	0.054 (3)	0.049 (3)	−0.0035 (19)	0.0076 (19)	0.004 (2)
N2	0.038 (3)	0.050 (3)	0.060 (3)	0.0088 (19)	0.008 (2)	0.009 (2)
C1	0.032 (2)	0.042 (3)	0.037 (2)	−0.0026 (19)	−0.0002 (19)	−0.001 (2)
C2	0.042 (3)	0.051 (3)	0.048 (3)	0.010 (2)	0.001 (2)	−0.004 (2)
C3	0.037 (3)	0.065 (4)	0.056 (4)	0.009 (3)	0.004 (3)	−0.005 (3)
C4	0.034 (3)	0.068 (4)	0.052 (3)	−0.011 (2)	0.008 (2)	−0.018 (3)
C5	0.039 (3)	0.049 (3)	0.044 (3)	−0.013 (2)	0.005 (2)	−0.013 (2)
C6	0.065 (4)	0.052 (3)	0.048 (3)	−0.021 (3)	0.014 (3)	−0.005 (3)
C7	0.079 (5)	0.045 (3)	0.055 (4)	−0.005 (3)	0.003 (4)	0.005 (3)
C8	0.063 (4)	0.047 (3)	0.068 (4)	0.013 (3)	0.003 (3)	0.009 (3)
C9	0.033 (3)	0.038 (2)	0.041 (3)	−0.0039 (18)	0.000 (2)	−0.006 (2)
C10	0.036 (3)	0.032 (2)	0.045 (3)	−0.0004 (18)	0.009 (2)	0.0039 (19)
C11	0.038 (3)	0.039 (3)	0.044 (3)	0.007 (2)	0.000 (2)	−0.003 (2)
C12	0.037 (3)	0.055 (3)	0.054 (3)	0.004 (2)	0.004 (2)	−0.005 (3)
C13	0.051 (3)	0.040 (3)	0.046 (3)	−0.004 (2)	0.005 (2)	0.001 (2)
C14	0.062 (4)	0.035 (3)	0.071 (4)	0.007 (2)	0.011 (3)	−0.010 (3)
C15	0.041 (3)	0.040 (3)	0.071 (4)	0.005 (2)	0.015 (3)	−0.001 (3)

Geometric parameters (Å, º)

Br1—C13	1.894 (6)	C5—C9	1.395 (8)
S1—O2	1.418 (4)	C5—C6	1.400 (9)
S1—O1	1.437 (4)	C6—C7	1.359 (11)
S1—N1	1.643 (5)	C6—H6	0.9300
S1—C10	1.765 (5)	C7—C8	1.420 (11)
N1—C1	1.417 (7)	C7—H7	0.9300
N1—H1N	0.8600	C8—H8	0.9300
N2—C8	1.324 (8)	C10—C11	1.381 (8)
N2—C9	1.372 (7)	C10—C15	1.399 (8)
C1—C2	1.368 (8)	C11—C12	1.378 (8)
C1—C9	1.413 (7)	C11—H11	0.9300
C2—C3	1.407 (9)	C12—C13	1.377 (8)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.353 (10)	C13—C14	1.392 (9)
C3—H3	0.9300	C14—C15	1.351 (9)
C4—C5	1.420 (9)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
O2—S1—O1	119.5 (3)	C6—C7—C8	119.8 (6)
O2—S1—N1	109.0 (3)	C6—C7—H7	120.1
O1—S1—N1	104.5 (3)	C8—C7—H7	120.1
O2—S1—C10	107.6 (3)	N2—C8—C7	121.7 (6)
O1—S1—C10	109.3 (3)	N2—C8—H8	119.1
N1—S1—C10	106.2 (2)	C7—C8—H8	119.1
C1—N1—S1	124.0 (4)	N2—C9—C5	123.1 (5)
C1—N1—H1N	118.0	N2—C9—C1	116.6 (5)
S1—N1—H1N	118.0	C5—C9—C1	120.2 (5)
C8—N2—C9	118.2 (5)	C11—C10—C15	120.8 (5)
C2—C1—C9	120.1 (5)	C11—C10—S1	120.0 (4)
C2—C1—N1	123.9 (5)	C15—C10—S1	119.3 (4)
C9—C1—N1	116.0 (5)	C12—C11—C10	119.2 (5)
C1—C2—C3	119.2 (6)	C12—C11—H11	120.4
C1—C2—H2	120.4	C10—C11—H11	120.4
C3—C2—H2	120.4	C13—C12—C11	119.5 (5)
C4—C3—C2	121.9 (6)	C13—C12—H12	120.3
C4—C3—H3	119.0	C11—C12—H12	120.3
C2—C3—H3	119.0	C12—C13—C14	121.2 (5)
C3—C4—C5	119.7 (6)	C12—C13—Br1	119.4 (5)
C3—C4—H4	120.2	C14—C13—Br1	119.4 (4)
C5—C4—H4	120.2	C15—C14—C13	119.4 (5)
C9—C5—C6	117.5 (5)	C15—C14—H14	120.3
C9—C5—C4	118.8 (6)	C13—C14—H14	120.3
C6—C5—C4	123.7 (6)	C14—C15—C10	119.8 (6)
C7—C6—C5	119.7 (6)	C14—C15—H15	120.1
C7—C6—H6	120.2	C10—C15—H15	120.1
C5—C6—H6	120.2
O2—S1—N1—C1	−60.6 (5)	C4—C5—C9—C1	−2.1 (7)
O1—S1—N1—C1	170.6 (4)	C2—C1—C9—N2	178.8 (5)
C10—S1—N1—C1	55.1 (5)	N1—C1—C9—N2	−0.1 (7)
S1—N1—C1—C2	39.9 (7)	C2—C1—C9—C5	0.7 (8)
S1—N1—C1—C9	−141.2 (4)	N1—C1—C9—C5	−178.2 (5)
C9—C1—C2—C3	0.6 (8)	O2—S1—C10—C11	23.2 (5)
N1—C1—C2—C3	179.4 (5)	O1—S1—C10—C11	154.4 (4)
C1—C2—C3—C4	−0.4 (9)	N1—S1—C10—C11	−93.4 (5)
C2—C3—C4—C5	−1.0 (9)	O2—S1—C10—C15	−157.5 (5)
C3—C4—C5—C9	2.3 (8)	O1—S1—C10—C15	−26.4 (5)
C3—C4—C5—C6	−177.8 (6)	N1—S1—C10—C15	85.9 (5)
C9—C5—C6—C7	−0.6 (8)	C15—C10—C11—C12	−3.8 (9)
C4—C5—C6—C7	179.5 (6)	S1—C10—C11—C12	175.5 (4)
C5—C6—C7—C8	1.3 (10)	C10—C11—C12—C13	1.8 (9)
C9—N2—C8—C7	0.9 (10)	C11—C12—C13—C14	1.3 (10)
C6—C7—C8—N2	−1.5 (11)	C11—C12—C13—Br1	−178.0 (4)
C8—N2—C9—C5	−0.1 (8)	C12—C13—C14—C15	−2.4 (10)
C8—N2—C9—C1	−178.2 (5)	Br1—C13—C14—C15	177.0 (5)
C6—C5—C9—N2	0.0 (8)	C13—C14—C15—C10	0.4 (10)
C4—C5—C9—N2	179.9 (5)	C11—C10—C15—C14	2.7 (10)
C6—C5—C9—C1	178.0 (5)	S1—C10—C15—C14	−176.5 (5)