Conformational preferences in 2-­nitrophenylthiolates: S-(2-nitro­phenyl) 4-toluenethiosulfonate

In the title compound, C₁₃H₁₁NO₄S₂, the nitro group is rotated by 44.1 (1)° out of the plane of the adjacent aryl ring and the toluene­thio­sulfonate group is almost orthogonal to the plane of the nitrated aryl ring. There are three types of C-H...O hydrogen bond in the structure [C...O range 3.324 (3)-3.503 (3) Å; C-H...O range 160-173°] and these link the mol­ecules into a three-dimensional framework.

Computing details

Data collection: SAINT (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

S-(2-nitrophenyl)-4-toluenethiosulfonate

Crystal data

C13H11NO4S2	F(000) = 640
Mr = 309.35	Dx = 1.476 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2971 (4) Å	Cell parameters from 2444 reflections
b = 7.0999 (4) Å	θ = 1.5–25.0°
c = 27.0085 (15) Å	µ = 0.39 mm^−1
β = 95.62 (1)°	T = 293 K
V = 1392.55 (13) Å^3	Block, colourless
Z = 4	0.38 × 0.20 × 0.18 mm

Data collection

Bruker SMART area detector diffractometer	2444 independent reflections
Radiation source: fine-focus sealed X-ray tube	1907 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Peak integration from area–detector frames (SAINT; Bruker, 1999) scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→8
Tmin = 0.865, Tmax = 0.933	k = −8→8
8612 measured reflections	l = −26→32

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.00	Calculated w = 1/[σ^2(Fo^2) + (0.0486P)^2] where P = (Fo^2 + 2Fc^2)/3
2444 reflections	(Δ/σ)max = 0.002
182 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.12940 (6)	0.95061 (7)	0.101469 (18)	0.04962 (16)
O11	0.09066 (19)	0.9791 (2)	0.15172 (5)	0.0647 (4)
O12	−0.01575 (19)	0.9573 (2)	0.06178 (6)	0.0735 (5)
S2	0.23278 (7)	0.67765 (7)	0.095716 (18)	0.05410 (17)
C11	0.3111 (2)	1.1000 (3)	0.08880 (7)	0.0438 (4)
C21	0.4349 (3)	1.1613 (3)	0.12751 (7)	0.0517 (5)
C31	0.5885 (3)	1.2604 (3)	0.11678 (8)	0.0553 (5)
C41	0.6213 (3)	1.2998 (3)	0.06807 (8)	0.0523 (5)
C411	0.7933 (3)	1.4025 (3)	0.05660 (10)	0.0739 (7)
C51	0.4922 (3)	1.2410 (3)	0.03043 (7)	0.0572 (5)
C61	0.3378 (3)	1.1401 (3)	0.03983 (7)	0.0525 (5)
C12	0.3979 (2)	0.6783 (2)	0.14820 (7)	0.0435 (4)
C22	0.3598 (2)	0.6260 (3)	0.19598 (7)	0.0464 (4)
N22	0.1748 (2)	0.5622 (3)	0.20599 (7)	0.0592 (5)
O221	0.0933 (2)	0.4512 (2)	0.17726 (7)	0.0785 (5)
O222	0.1153 (2)	0.6248 (3)	0.24346 (6)	0.0884 (6)
C32	0.4910 (3)	0.6312 (3)	0.23612 (8)	0.0603 (6)
C42	0.6671 (3)	0.6873 (3)	0.22917 (9)	0.0683 (6)
C52	0.7084 (3)	0.7405 (3)	0.18251 (9)	0.0654 (6)
C62	0.5761 (3)	0.7372 (3)	0.14286 (8)	0.0539 (5)
H21	0.4147	1.1360	0.1603	0.062*
H31	0.6720	1.3017	0.1427	0.066*
H41A	0.8871	1.3872	0.0838	0.111*	0.50
H41B	0.7664	1.5340	0.0519	0.111*	0.50
H41C	0.8358	1.3516	0.0268	0.111*	0.50
H41D	0.7724	1.4613	0.0245	0.111*	0.50
H41E	0.8932	1.3145	0.0565	0.111*	0.50
H41F	0.8237	1.4969	0.0815	0.111*	0.50
H51	0.5100	1.2705	−0.0023	0.069*
H61	0.2537	1.0999	0.0139	0.063*
H32	0.4611	0.5973	0.2676	0.072*
H42	0.7579	0.6892	0.2559	0.082*
H52	0.8273	0.7792	0.1779	0.078*
H62	0.6065	0.7751	0.1117	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0434 (3)	0.0591 (3)	0.0467 (3)	−0.0008 (2)	0.0062 (2)	0.0057 (2)
O11	0.0653 (9)	0.0765 (10)	0.0566 (9)	−0.0017 (7)	0.0271 (7)	−0.0019 (7)
O12	0.0501 (8)	0.0948 (12)	0.0724 (11)	−0.0035 (8)	−0.0107 (7)	0.0192 (9)
S2	0.0671 (3)	0.0489 (3)	0.0459 (3)	−0.0117 (2)	0.0037 (2)	−0.0026 (2)
C11	0.0479 (10)	0.0417 (10)	0.0423 (11)	0.0039 (8)	0.0071 (8)	0.0023 (8)
C21	0.0684 (13)	0.0470 (12)	0.0402 (11)	−0.0022 (9)	0.0072 (9)	−0.0005 (8)
C31	0.0629 (12)	0.0470 (11)	0.0538 (12)	−0.0083 (10)	−0.0052 (10)	−0.0039 (9)
C41	0.0555 (11)	0.0394 (11)	0.0631 (13)	0.0012 (9)	0.0115 (10)	0.0023 (9)
C411	0.0654 (14)	0.0683 (15)	0.0893 (17)	−0.0116 (12)	0.0131 (13)	0.0069 (13)
C51	0.0668 (13)	0.0618 (13)	0.0446 (12)	−0.0055 (11)	0.0143 (10)	0.0067 (10)
C61	0.0558 (12)	0.0602 (13)	0.0405 (11)	−0.0035 (9)	0.0004 (9)	0.0035 (9)
C12	0.0448 (10)	0.0391 (10)	0.0478 (11)	0.0024 (8)	0.0114 (8)	0.0008 (8)
C22	0.0388 (10)	0.0477 (11)	0.0540 (12)	0.0059 (8)	0.0117 (9)	0.0085 (9)
N22	0.0447 (9)	0.0770 (13)	0.0571 (11)	0.0073 (9)	0.0120 (9)	0.0219 (10)
O221	0.0657 (10)	0.0801 (12)	0.0908 (13)	−0.0226 (9)	0.0131 (9)	0.0141 (10)
O222	0.0546 (9)	0.1543 (18)	0.0600 (10)	0.0140 (10)	0.0240 (8)	0.0116 (10)
C32	0.0514 (12)	0.0781 (16)	0.0521 (13)	0.0119 (10)	0.0088 (10)	0.0126 (11)
C42	0.0464 (12)	0.0859 (17)	0.0706 (15)	0.0053 (11)	−0.0034 (11)	0.0076 (13)
C52	0.0403 (11)	0.0693 (15)	0.0880 (17)	−0.0023 (10)	0.0130 (11)	0.0056 (13)
C62	0.0513 (11)	0.0514 (12)	0.0620 (13)	−0.0007 (9)	0.0212 (10)	0.0062 (10)

Geometric parameters (Å, º)

S1—O11	1.4275 (15)	C411—H41F	0.9600
S1—O12	1.4320 (14)	C51—C61	1.380 (3)
S1—C11	1.7575 (19)	C51—H51	0.9300
S1—S2	2.0910 (8)	C61—H61	0.9300
S2—C12	1.7683 (19)	C12—C62	1.387 (2)
C11—C21	1.383 (3)	C12—C22	1.397 (3)
C11—C61	1.385 (3)	C22—C32	1.375 (3)
C21—C31	1.378 (3)	C22—N22	1.474 (2)
C21—H21	0.9300	N22—O221	1.219 (2)
C31—C41	1.389 (3)	N22—O222	1.223 (2)
C31—H31	0.9300	C32—C42	1.375 (3)
C41—C51	1.381 (3)	C32—H32	0.9300
C41—C411	1.510 (3)	C42—C52	1.377 (3)
C411—H41A	0.9600	C42—H42	0.9300
C411—H41B	0.9600	C52—C62	1.370 (3)
C411—H41C	0.9600	C52—H52	0.9300
C411—H41D	0.9600	C62—H62	0.9300
C411—H41E	0.9600
O11—S1—O12	120.41 (10)	C41—C411—H41F	109.5
O11—S1—C11	108.85 (9)	H41A—C411—H41F	56.3
O12—S1—C11	110.56 (9)	H41B—C411—H41F	56.3
O11—S1—S2	107.96 (7)	H41C—C411—H41F	141.1
O12—S1—S2	102.75 (8)	H41D—C411—H41F	109.5
C11—S1—S2	105.09 (6)	H41E—C411—H41F	109.5
C12—S2—S1	99.24 (6)	C61—C51—C41	122.14 (18)
C21—C11—C61	120.95 (18)	C61—C51—H51	118.9
C21—C11—S1	119.48 (14)	C41—C51—H51	118.9
C61—C11—S1	119.30 (15)	C51—C61—C11	118.44 (19)
C31—C21—C11	119.09 (18)	C51—C61—H61	120.8
C31—C21—H21	120.5	C11—C61—H61	120.8
C11—C21—H21	120.5	C62—C12—C22	116.72 (18)
C21—C31—C41	121.42 (19)	C62—C12—S2	119.31 (15)
C21—C31—H31	119.3	C22—C12—S2	123.95 (14)
C41—C31—H31	119.3	C32—C22—C12	122.35 (17)
C51—C41—C31	117.92 (18)	C32—C22—N22	116.33 (17)
C51—C41—C411	121.0 (2)	C12—C22—N22	121.32 (18)
C31—C41—C411	121.0 (2)	O221—N22—O222	124.84 (19)
C41—C411—H41A	109.5	O221—N22—C22	118.70 (18)
C41—C411—H41B	109.5	O222—N22—C22	116.5 (2)
H41A—C411—H41B	109.5	C22—C32—C42	119.2 (2)
C41—C411—H41C	109.5	C22—C32—H32	120.4
H41A—C411—H41C	109.5	C42—C32—H32	120.4
H41B—C411—H41C	109.5	C32—C42—C52	119.7 (2)
C41—C411—H41D	109.5	C32—C42—H42	120.2
H41A—C411—H41D	141.1	C52—C42—H42	120.2
H41B—C411—H41D	56.3	C62—C52—C42	120.68 (19)
H41C—C411—H41D	56.3	C62—C52—H52	119.7
C41—C411—H41E	109.5	C42—C52—H52	119.7
H41A—C411—H41E	56.3	C52—C62—C12	121.33 (19)
H41B—C411—H41E	141.1	C52—C62—H62	119.3
H41C—C411—H41E	56.3	C12—C62—H62	119.3
H41D—C411—H41E	109.5
O11—S1—S2—C12	−47.92 (9)	S1—C11—C61—C51	−173.24 (16)
O12—S1—S2—C12	−176.16 (9)	S1—S2—C12—C62	−89.91 (15)
C11—S1—S2—C12	68.13 (9)	S1—S2—C12—C22	88.75 (15)
O11—S1—C11—C21	25.01 (18)	C62—C12—C22—C32	−0.2 (3)
O12—S1—C11—C21	159.38 (15)	S2—C12—C22—C32	−178.88 (16)
S2—S1—C11—C21	−90.42 (15)	C62—C12—C22—N22	179.66 (18)
O11—S1—C11—C61	−160.94 (15)	S2—C12—C22—N22	1.0 (3)
O12—S1—C11—C61	−26.57 (19)	C12—C22—N22—O221	44.2 (3)
S2—S1—C11—C61	83.62 (16)	C32—C22—N22—O221	−135.9 (2)
C61—C11—C21—C31	−1.3 (3)	C12—C22—N22—O222	−136.55 (19)
S1—C11—C21—C31	172.65 (15)	C32—C22—N22—O222	43.3 (2)
C11—C21—C31—C41	0.0 (3)	C12—C22—C32—C42	−0.9 (3)
C21—C31—C41—C51	1.7 (3)	N22—C22—C32—C42	179.2 (2)
C21—C31—C41—C411	−177.8 (2)	C22—C32—C42—C52	1.2 (3)
C31—C41—C51—C61	−2.4 (3)	C32—C42—C52—C62	−0.4 (4)
C411—C41—C51—C61	177.2 (2)	C42—C52—C62—C12	−0.7 (3)
C41—C51—C61—C11	1.2 (3)	C22—C12—C62—C52	1.0 (3)
C21—C11—C61—C51	0.7 (3)	S2—C12—C62—C52	179.78 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···O11^i	0.93	2.40	3.324 (3)	173
C52—H52···O11^ii	0.93	2.54	3.435 (3)	160
C61—H61···012^iii	0.93	2.58	3.503 (3)	171

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