4-Fluoro-N-(quinolin-8-yl)benzene­sulfonamide

In the crystal structure of the title compound, C₁₅H₁₁FN₂O₂S, the torsion angle about the N—S bond between the quinoline ring system and the benzene ring is −59.0 (2)°. The sulfonamide H atom forms one intra­molecular hydrogen bond to the quinoline N atom [N—H...N = 2.25 (2) Å] and an intermolecular hydrogen bond to a sulfonyl O atom [N—H...O =2.53 (2) Å]. The C atom adjacent to the quinoline N atom forms one inter­molecular contact to the F atom [H...F = 2.48 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.035
• wR factor = 0.096
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

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Computing details

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.

4-Fluoro-N-(quinolin-8-yl)benzenesulfonamide

Crystal data

C15H11FN2O2S	F(000) = 624
Mr = 302.32	Dx = 1.492 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.984 (1) Å	θ = 5.2–19.0°
b = 12.408 (1) Å	µ = 2.31 mm^−1
c = 9.2792 (7) Å	T = 299 K
β = 102.74 (1)°	Prism, colourless
V = 1345.82 (19) Å^3	0.28 × 0.28 × 0.23 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.040
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 3.8°
Graphite monochromator	h = −14→14
ω/2θ scans	k = −14→0
4785 measured reflections	l = −11→11
2396 independent reflections	3 standard reflections every 120 min
2064 reflections with I > 2σ(I)	intensity decay: 1.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Only H-atom coordinates refined
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.2885P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2396 reflections	Δρmax = 0.25 e Å^−3
224 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (5)

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
C1	0.71589 (14)	0.85829 (14)	−0.00110 (19)	0.0389 (4)
C2	0.67827 (19)	0.78148 (16)	0.0824 (2)	0.0522 (5)
H2	0.731 (2)	0.7384 (19)	0.155 (3)	0.063*
C3	0.5598 (2)	0.76395 (17)	0.0665 (3)	0.0590 (5)
H3	0.537 (2)	0.711 (2)	0.129 (3)	0.071*
C4	0.48090 (18)	0.82061 (16)	−0.0310 (2)	0.0528 (5)
H4	0.399 (2)	0.8114 (18)	−0.037 (3)	0.063*
C5	0.51665 (14)	0.89965 (14)	−0.11977 (19)	0.0406 (4)
C6	0.44042 (16)	0.96263 (17)	−0.2239 (2)	0.0492 (5)
H6	0.3575 (19)	0.9526 (17)	−0.237 (2)	0.059*
C7	0.48158 (17)	1.03587 (19)	−0.3056 (2)	0.0567 (5)
H7	0.435 (2)	1.0812 (19)	−0.378 (3)	0.068*
C8	0.60064 (18)	1.04836 (19)	−0.2853 (3)	0.0579 (5)
H8	0.636 (2)	1.1024 (19)	−0.343 (3)	0.070*
C9	0.63496 (14)	0.91875 (13)	−0.10603 (18)	0.0368 (4)
C10	0.88911 (13)	0.96832 (14)	0.28126 (18)	0.0379 (4)
C11	0.88617 (15)	1.07796 (15)	0.2484 (2)	0.0435 (4)
H11	0.9046 (18)	1.0996 (17)	0.164 (2)	0.052*
C12	0.85449 (16)	1.14986 (16)	0.3441 (2)	0.0470 (4)
H12	0.8510 (19)	1.2192 (18)	0.322 (2)	0.056*
C13	0.82711 (15)	1.11141 (15)	0.4706 (2)	0.0454 (4)
C14	0.83058 (16)	1.00411 (17)	0.5072 (2)	0.0480 (5)
H14	0.8130 (19)	0.9816 (17)	0.591 (3)	0.058*
C15	0.86131 (15)	0.93124 (15)	0.4100 (2)	0.0429 (4)
H15	0.8653 (18)	0.8570 (17)	0.435 (2)	0.052*
N1	0.83277 (13)	0.88192 (13)	0.00576 (18)	0.0439 (4)
H1N	0.8452 (18)	0.9325 (17)	−0.057 (2)	0.053*
N2	0.67594 (12)	0.99271 (13)	−0.18913 (18)	0.0474 (4)
O1	0.92967 (12)	0.77158 (11)	0.22024 (17)	0.0588 (4)
O2	1.03297 (10)	0.91564 (13)	0.12012 (16)	0.0574 (4)
F1	0.79543 (12)	1.18327 (11)	0.56395 (15)	0.0698 (4)
S1	0.93137 (3)	0.87681 (4)	0.15878 (5)	0.04345 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0407 (9)	0.0383 (8)	0.0395 (9)	0.0003 (7)	0.0128 (7)	−0.0069 (7)
C2	0.0585 (12)	0.0456 (10)	0.0527 (11)	−0.0037 (9)	0.0128 (9)	0.0034 (9)
C3	0.0694 (14)	0.0511 (11)	0.0601 (12)	−0.0188 (10)	0.0217 (11)	0.0028 (10)
C4	0.0485 (11)	0.0559 (11)	0.0572 (12)	−0.0193 (9)	0.0183 (9)	−0.0121 (9)
C5	0.0389 (9)	0.0431 (9)	0.0414 (9)	−0.0069 (7)	0.0124 (7)	−0.0161 (7)
C6	0.0359 (9)	0.0578 (11)	0.0523 (11)	−0.0011 (8)	0.0067 (8)	−0.0146 (9)
C7	0.0441 (11)	0.0648 (12)	0.0582 (12)	0.0101 (9)	0.0048 (9)	0.0052 (10)
C8	0.0479 (11)	0.0640 (12)	0.0623 (13)	0.0050 (9)	0.0129 (9)	0.0181 (10)
C9	0.0381 (8)	0.0369 (8)	0.0368 (8)	−0.0017 (7)	0.0116 (7)	−0.0082 (7)
C10	0.0274 (8)	0.0443 (9)	0.0406 (9)	0.0015 (6)	0.0043 (6)	0.0074 (7)
C11	0.0379 (9)	0.0461 (10)	0.0479 (10)	−0.0034 (7)	0.0124 (7)	0.0097 (8)
C12	0.0396 (9)	0.0409 (9)	0.0603 (11)	−0.0087 (8)	0.0108 (8)	0.0030 (9)
C13	0.0354 (9)	0.0545 (11)	0.0453 (10)	−0.0079 (7)	0.0066 (7)	−0.0106 (8)
C14	0.0420 (10)	0.0633 (12)	0.0383 (9)	−0.0062 (8)	0.0083 (8)	0.0062 (9)
C15	0.0373 (9)	0.0471 (10)	0.0431 (9)	0.0001 (7)	0.0061 (7)	0.0111 (8)
N1	0.0387 (8)	0.0509 (9)	0.0435 (8)	0.0056 (6)	0.0123 (6)	0.0040 (7)
N2	0.0379 (8)	0.0538 (9)	0.0518 (9)	0.0023 (6)	0.0127 (7)	0.0092 (7)
O1	0.0603 (9)	0.0479 (7)	0.0695 (9)	0.0238 (6)	0.0173 (7)	0.0169 (7)
O2	0.0328 (7)	0.0795 (10)	0.0630 (8)	0.0131 (6)	0.0174 (6)	0.0126 (7)
F1	0.0740 (8)	0.0699 (8)	0.0687 (8)	−0.0086 (6)	0.0228 (6)	−0.0238 (6)
S1	0.0335 (2)	0.0490 (3)	0.0488 (3)	0.01323 (17)	0.01101 (18)	0.00902 (18)

Geometric parameters (Å, º)

C1—C2	1.366 (3)	C9—N2	1.358 (2)
C1—N1	1.419 (2)	C10—C15	1.388 (3)
C1—C9	1.426 (2)	C10—C11	1.393 (2)
C2—C3	1.411 (3)	C10—S1	1.7582 (18)
C2—H2	0.98 (2)	C11—C12	1.370 (3)
C3—C4	1.353 (3)	C11—H11	0.90 (2)
C3—H3	0.96 (3)	C12—C13	1.372 (3)
C4—C5	1.407 (3)	C12—H12	0.88 (2)
C4—H4	0.98 (2)	C13—F1	1.354 (2)
C5—C6	1.411 (3)	C13—C14	1.372 (3)
C5—C9	1.415 (2)	C14—C15	1.383 (3)
C6—C7	1.345 (3)	C14—H14	0.89 (2)
C6—H6	0.98 (2)	C15—H15	0.95 (2)
C7—C8	1.406 (3)	N1—S1	1.6360 (16)
C7—H7	0.96 (2)	N1—H1N	0.89 (2)
C8—N2	1.316 (3)	O1—S1	1.4268 (14)
C8—H8	1.01 (2)	O2—S1	1.4269 (14)
C2—C1—N1	124.39 (17)	C15—C10—S1	120.04 (14)
C2—C1—C9	119.62 (17)	C11—C10—S1	119.08 (14)
N1—C1—C9	115.97 (15)	C12—C11—C10	119.40 (18)
C1—C2—C3	119.89 (19)	C12—C11—H11	121.7 (13)
C1—C2—H2	121.8 (14)	C10—C11—H11	118.9 (13)
C3—C2—H2	118.3 (14)	C11—C12—C13	118.74 (18)
C4—C3—C2	121.9 (2)	C11—C12—H12	119.1 (15)
C4—C3—H3	120.6 (15)	C13—C12—H12	122.1 (15)
C2—C3—H3	117.5 (15)	F1—C13—C14	118.55 (17)
C3—C4—C5	119.70 (19)	F1—C13—C12	118.15 (17)
C3—C4—H4	121.3 (14)	C14—C13—C12	123.31 (18)
C5—C4—H4	118.8 (14)	C13—C14—C15	118.08 (18)
C4—C5—C6	123.54 (17)	C13—C14—H14	121.2 (14)
C4—C5—C9	119.49 (17)	C15—C14—H14	120.7 (14)
C6—C5—C9	116.97 (17)	C14—C15—C10	119.58 (17)
C7—C6—C5	119.86 (17)	C14—C15—H15	119.1 (13)
C7—C6—H6	120.4 (13)	C10—C15—H15	121.3 (13)
C5—C6—H6	119.8 (13)	C1—N1—S1	123.23 (13)
C6—C7—C8	119.11 (19)	C1—N1—H1N	115.0 (14)
C6—C7—H7	124.5 (15)	S1—N1—H1N	113.6 (14)
C8—C7—H7	116.4 (15)	C8—N2—C9	117.37 (16)
N2—C8—C7	123.8 (2)	O1—S1—O2	119.85 (9)
N2—C8—H8	114.0 (14)	O1—S1—N1	108.13 (9)
C7—C8—H8	122.1 (14)	O2—S1—N1	105.18 (8)
N2—C9—C5	122.85 (16)	O1—S1—C10	107.52 (9)
N2—C9—C1	117.79 (15)	O2—S1—C10	109.14 (9)
C5—C9—C1	119.36 (16)	N1—S1—C10	106.26 (7)
C15—C10—C11	120.87 (17)
N1—C1—C2—C3	−179.68 (18)	C11—C12—C13—F1	−179.69 (15)
C9—C1—C2—C3	−1.3 (3)	C11—C12—C13—C14	0.5 (3)
C1—C2—C3—C4	0.7 (3)	F1—C13—C14—C15	179.00 (15)
C2—C3—C4—C5	0.0 (3)	C12—C13—C14—C15	−1.2 (3)
C3—C4—C5—C6	−179.84 (19)	C13—C14—C15—C10	1.0 (3)
C3—C4—C5—C9	0.1 (3)	C11—C10—C15—C14	−0.2 (3)
C4—C5—C6—C7	−179.36 (18)	S1—C10—C15—C14	178.59 (13)
C9—C5—C6—C7	0.7 (3)	C2—C1—N1—S1	−35.3 (2)
C5—C6—C7—C8	−0.1 (3)	C9—C1—N1—S1	146.22 (13)
C6—C7—C8—N2	−0.5 (4)	C7—C8—N2—C9	0.4 (3)
C4—C5—C9—N2	179.18 (16)	C5—C9—N2—C8	0.3 (3)
C6—C5—C9—N2	−0.9 (2)	C1—C9—N2—C8	−179.77 (18)
C4—C5—C9—C1	−0.7 (2)	C1—N1—S1—O1	56.16 (16)
C6—C5—C9—C1	179.23 (15)	C1—N1—S1—O2	−174.68 (14)
C2—C1—C9—N2	−178.59 (16)	C1—N1—S1—C10	−59.02 (15)
N1—C1—C9—N2	0.0 (2)	C15—C10—S1—O1	−0.28 (16)
C2—C1—C9—C5	1.3 (2)	C11—C10—S1—O1	178.51 (13)
N1—C1—C9—C5	179.85 (14)	C15—C10—S1—O2	−131.74 (14)
C15—C10—C11—C12	−0.5 (3)	C11—C10—S1—O2	47.06 (15)
S1—C10—C11—C12	−179.30 (13)	C15—C10—S1—N1	115.31 (14)
C10—C11—C12—C13	0.4 (3)	C11—C10—S1—N1	−65.89 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.89 (2)	2.25 (2)	2.682 (2)	109.3 (16)
N1—H1N···O2^i	0.89 (2)	2.53 (2)	3.330 (2)	149.9 (18)
C8—H8···F1^ii	1.01 (2)	2.48 (3)	3.413 (3)	154.1 (19)

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