2-Amino­quinolin-8-yl 3,5-difluoro­benzene­sulfonate

The mol­ecular packing of the title compound, C₁₅H₁₀F₂N₂O₃S, is stabilized by a hydrogen-bonded network. Both H atoms of the amino group form inter­molecular hydrogen bonds of types N—H...N [2.26 (5) Å] and N—H...O [2.30 (5) Å]. The nearly planar quinoline system and the aromatic ring of the toluene­sulfonate group form a dihedral angle of 31.1 (6)°; the torsion angle about the central C—O—S—C bridge is −120.4 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.062
• wR factor = 0.186
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.104
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.16
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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      1.156
            Tmax scaled      0.822 Tmin scaled      0.466

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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 Software (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.

2-Aminoquinolin-8-yl 3,5-difluorobenzenesulfonate

Crystal data

C15H10F2N2O3S	Z = 2
Mr = 336.31	F(000) = 344
Triclinic, P1	Dx = 1.594 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 7.7926 (7) Å	Cell parameters from 25 reflections
b = 9.253 (1) Å	θ = 4.5–25.4°
c = 9.795 (1) Å	µ = 2.45 mm^−1
α = 90.233 (9)°	T = 299 K
β = 96.787 (8)°	Plate, light brown
γ = 92.516 (8)°	0.40 × 0.25 × 0.08 mm
V = 700.61 (12) Å^3

Data collection

Nonius CAD-4 diffractometer	2028 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.104
Graphite monochromator	θmax = 66.9°, θmin = 4.6°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.403, Tmax = 0.711	l = −11→1
2699 measured reflections	3 standard reflections every 120 min
2491 independent reflections	intensity decay: 1.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.187	w = 1/[σ^2(Fo^2) + (0.1277P)^2 + 0.1408P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2491 reflections	Δρmax = 0.65 e Å^−3
215 parameters	Δρmin = −0.65 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: 0.0070 (19)

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	−0.1362 (4)	0.8005 (3)	0.2531 (3)	0.0401 (7)
C2	−0.2260 (5)	0.8959 (4)	0.3205 (4)	0.0534 (9)
H2	−0.2288	0.8890	0.4149	0.064*
C3	−0.3136 (5)	1.0042 (4)	0.2458 (5)	0.0613 (10)
H3	−0.3764	1.0692	0.2903	0.074*
C4	−0.3070 (5)	1.0146 (4)	0.1077 (4)	0.0543 (9)
H4	−0.3648	1.0876	0.0591	0.065*
C5	−0.2145 (4)	0.9168 (3)	0.0371 (4)	0.0419 (7)
C6	−0.1984 (5)	0.9241 (4)	−0.1058 (4)	0.0478 (8)
H6	−0.2548	0.9947	−0.1589	0.057*
C7	−0.1026 (5)	0.8299 (4)	−0.1647 (3)	0.0479 (8)
H7	−0.0871	0.8382	−0.2571	0.057*
C8	−0.0254 (4)	0.7174 (3)	−0.0840 (3)	0.0399 (7)
C9	−0.1282 (4)	0.8045 (3)	0.1099 (3)	0.0371 (7)
C10	0.2680 (4)	0.6070 (4)	0.3472 (3)	0.0397 (7)
C11	0.2927 (4)	0.4720 (4)	0.4031 (3)	0.0448 (8)
H11	0.2341	0.4395	0.4752	0.054*
C12	0.4082 (4)	0.3877 (4)	0.3471 (4)	0.0507 (9)
C13	0.4975 (5)	0.4324 (4)	0.2406 (4)	0.0560 (10)
H13	0.5762	0.3740	0.2055	0.067*
C14	0.4648 (5)	0.5671 (5)	0.1888 (4)	0.0559 (10)
C15	0.3527 (5)	0.6581 (4)	0.2395 (4)	0.0499 (8)
H15	0.3345	0.7497	0.2032	0.060*
N1	−0.0361 (3)	0.7046 (3)	0.0501 (3)	0.0382 (6)
N2	0.0685 (5)	0.6191 (4)	−0.1436 (3)	0.0544 (8)
H21N	0.082 (6)	0.530 (5)	−0.104 (4)	0.065*
H22N	0.055 (6)	0.615 (5)	−0.227 (5)	0.065*
O1	0.1084 (4)	0.6744 (3)	0.5536 (2)	0.0594 (7)
O2	0.1830 (3)	0.8701 (3)	0.3978 (3)	0.0549 (7)
O3	−0.0521 (3)	0.6880 (2)	0.3293 (2)	0.0425 (6)
F1	0.4373 (4)	0.2567 (3)	0.4009 (3)	0.0747 (8)
F2	0.5515 (4)	0.6152 (3)	0.0855 (3)	0.0836 (9)
S1	0.12907 (11)	0.72382 (9)	0.41893 (7)	0.0413 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0391 (16)	0.0387 (17)	0.0432 (16)	0.0087 (12)	0.0055 (13)	0.0012 (13)
C2	0.057 (2)	0.052 (2)	0.053 (2)	0.0095 (16)	0.0098 (16)	−0.0072 (16)
C3	0.053 (2)	0.053 (2)	0.080 (3)	0.0198 (17)	0.0071 (19)	−0.0119 (19)
C4	0.0460 (19)	0.0412 (19)	0.073 (3)	0.0149 (15)	−0.0071 (17)	0.0008 (17)
C5	0.0347 (15)	0.0340 (16)	0.0552 (19)	0.0024 (12)	−0.0027 (13)	0.0057 (13)
C6	0.0471 (18)	0.0400 (18)	0.0532 (19)	0.0016 (14)	−0.0073 (15)	0.0165 (14)
C7	0.055 (2)	0.0464 (19)	0.0416 (17)	−0.0035 (15)	0.0033 (14)	0.0122 (14)
C8	0.0428 (17)	0.0374 (16)	0.0396 (16)	−0.0023 (13)	0.0062 (13)	0.0064 (12)
C9	0.0347 (15)	0.0325 (15)	0.0439 (16)	0.0040 (11)	0.0031 (12)	0.0064 (12)
C10	0.0392 (16)	0.0435 (17)	0.0385 (15)	0.0049 (13)	0.0116 (13)	0.0033 (13)
C11	0.0425 (17)	0.0480 (19)	0.0438 (17)	0.0053 (14)	0.0040 (13)	0.0061 (14)
C12	0.0430 (18)	0.048 (2)	0.059 (2)	0.0082 (15)	−0.0009 (15)	−0.0017 (16)
C13	0.0418 (19)	0.066 (3)	0.063 (2)	0.0059 (16)	0.0133 (16)	−0.0132 (18)
C14	0.049 (2)	0.068 (2)	0.053 (2)	−0.0159 (17)	0.0238 (16)	−0.0091 (18)
C15	0.057 (2)	0.0471 (19)	0.0469 (18)	−0.0079 (15)	0.0161 (15)	0.0053 (15)
N1	0.0427 (14)	0.0364 (14)	0.0372 (13)	0.0078 (11)	0.0098 (11)	0.0079 (10)
N2	0.078 (2)	0.0507 (18)	0.0390 (15)	0.0142 (15)	0.0205 (15)	0.0067 (13)
O1	0.0755 (18)	0.0769 (19)	0.0294 (12)	0.0230 (14)	0.0139 (11)	0.0103 (11)
O2	0.0626 (16)	0.0402 (13)	0.0608 (16)	0.0034 (11)	0.0024 (12)	0.0008 (11)
O3	0.0494 (13)	0.0376 (12)	0.0412 (12)	0.0040 (9)	0.0080 (10)	0.0093 (9)
F1	0.0861 (18)	0.0569 (15)	0.0828 (17)	0.0330 (13)	0.0057 (14)	0.0101 (12)
F2	0.0913 (19)	0.0869 (19)	0.0800 (17)	−0.0311 (15)	0.0542 (15)	−0.0156 (14)
S1	0.0500 (5)	0.0430 (5)	0.0323 (4)	0.0089 (3)	0.0074 (3)	0.0039 (3)

Geometric parameters (Å, º)

C1—C2	1.365 (5)	C10—C11	1.378 (4)
C1—C9	1.411 (4)	C10—C15	1.384 (4)
C1—O3	1.422 (4)	C10—S1	1.764 (3)
C2—C3	1.398 (5)	C11—C12	1.376 (5)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.363 (5)	C12—F1	1.341 (4)
C3—H3	0.9300	C12—C13	1.376 (5)
C4—C5	1.410 (5)	C13—C14	1.371 (6)
C4—H4	0.9300	C13—H13	0.9300
C5—C9	1.412 (4)	C14—F2	1.348 (4)
C5—C6	1.421 (5)	C14—C15	1.372 (5)
C6—C7	1.344 (5)	C15—H15	0.9300
C6—H6	0.9300	N2—H21N	0.92 (5)
C7—C8	1.421 (5)	N2—H22N	0.82 (5)
C7—H7	0.9300	O1—S1	1.422 (2)
C8—N1	1.331 (4)	O2—S1	1.423 (3)
C8—N2	1.362 (4)	O3—S1	1.593 (2)
C9—N1	1.366 (4)
C2—C1—C9	123.2 (3)	C11—C10—S1	119.2 (2)
C2—C1—O3	118.6 (3)	C15—C10—S1	117.9 (3)
C9—C1—O3	118.1 (3)	C12—C11—C10	116.9 (3)
C1—C2—C3	119.1 (4)	C12—C11—H11	121.6
C1—C2—H2	120.4	C10—C11—H11	121.6
C3—C2—H2	120.4	F1—C12—C11	118.3 (3)
C4—C3—C2	120.0 (3)	F1—C12—C13	118.5 (3)
C4—C3—H3	120.0	C11—C12—C13	123.2 (4)
C2—C3—H3	120.0	C14—C13—C12	116.8 (3)
C3—C4—C5	121.3 (3)	C14—C13—H13	121.6
C3—C4—H4	119.3	C12—C13—H13	121.6
C5—C4—H4	119.3	F2—C14—C13	118.4 (4)
C4—C5—C9	119.7 (3)	F2—C14—C15	118.0 (4)
C4—C5—C6	124.1 (3)	C13—C14—C15	123.6 (3)
C9—C5—C6	116.2 (3)	C14—C15—C10	116.7 (3)
C7—C6—C5	120.6 (3)	C14—C15—H15	121.6
C7—C6—H6	119.7	C10—C15—H15	121.6
C5—C6—H6	119.7	C8—N1—C9	117.3 (3)
C6—C7—C8	119.1 (3)	C8—N2—H21N	119 (3)
C6—C7—H7	120.4	C8—N2—H22N	116 (3)
C8—C7—H7	120.4	H21N—N2—H22N	112 (4)
N1—C8—N2	117.4 (3)	C1—O3—S1	119.1 (2)
N1—C8—C7	123.0 (3)	O1—S1—O2	120.25 (17)
N2—C8—C7	119.6 (3)	O1—S1—O3	105.50 (15)
N1—C9—C1	119.6 (3)	O2—S1—O3	109.49 (13)
N1—C9—C5	123.7 (3)	O1—S1—C10	107.87 (15)
C1—C9—C5	116.7 (3)	O2—S1—C10	109.60 (16)
C11—C10—C15	122.9 (3)	O3—S1—C10	102.66 (14)
C9—C1—C2—C3	−0.6 (6)	F1—C12—C13—C14	−179.7 (3)
O3—C1—C2—C3	−178.0 (3)	C11—C12—C13—C14	−1.0 (6)
C1—C2—C3—C4	−0.8 (6)	C12—C13—C14—F2	179.2 (3)
C2—C3—C4—C5	0.7 (6)	C12—C13—C14—C15	1.5 (6)
C3—C4—C5—C9	0.8 (5)	F2—C14—C15—C10	−178.8 (3)
C3—C4—C5—C6	−178.2 (4)	C13—C14—C15—C10	−1.1 (6)
C4—C5—C6—C7	177.6 (3)	C11—C10—C15—C14	0.1 (5)
C9—C5—C6—C7	−1.4 (5)	S1—C10—C15—C14	177.7 (3)
C5—C6—C7—C8	3.6 (5)	N2—C8—N1—C9	179.0 (3)
C6—C7—C8—N1	−3.5 (5)	C7—C8—N1—C9	0.9 (4)
C6—C7—C8—N2	178.4 (3)	C1—C9—N1—C8	−176.8 (3)
C2—C1—C9—N1	−179.7 (3)	C5—C9—N1—C8	1.5 (4)
O3—C1—C9—N1	−2.2 (4)	C2—C1—O3—S1	−79.4 (4)
C2—C1—C9—C5	1.9 (5)	C9—C1—O3—S1	102.9 (3)
O3—C1—C9—C5	179.4 (3)	C1—O3—S1—O1	126.7 (2)
C4—C5—C9—N1	179.7 (3)	C1—O3—S1—O2	−4.0 (3)
C6—C5—C9—N1	−1.3 (5)	C1—O3—S1—C10	−120.4 (2)
C4—C5—C9—C1	−2.0 (5)	C11—C10—S1—O1	19.0 (3)
C6—C5—C9—C1	177.0 (3)	C15—C10—S1—O1	−158.7 (3)
C15—C10—C11—C12	0.3 (5)	C11—C10—S1—O2	151.5 (3)
S1—C10—C11—C12	−177.2 (3)	C15—C10—S1—O2	−26.2 (3)
C10—C11—C12—F1	178.8 (3)	C11—C10—S1—O3	−92.2 (3)
C10—C11—C12—C13	0.1 (5)	C15—C10—S1—O3	90.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21N···N1^i	0.92 (5)	2.26 (5)	3.144 (4)	162 (4)
N2—H22N···O1^ii	0.82 (5)	2.30 (5)	3.062 (4)	156 (4)

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