Conformational preferences in 2-nitrophenylthiolates: interplay between intra- and intermolecular forces; structures of (E)-1-(4-methyl-2-nitroben­zenethiolato)-2-phenylethene, S-(2-nitrophenyl)­benzenecarbothiolate and 1-(2-nitrophenylthio)-2,5-pyrrolidinedione

In (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenyl­ethene, C₁₅H₁₃NO₂S (1) (orthorhombic Pbca), the nitro group is almost coplanar with the adjacent aryl ring, but the dihedral angles between the nitro-aryl and styryl fragments is ∼121°. The molecules are linked by paired C—H...O hydrogen bonds in a chain of rings. In S-(2-nitrophenyl)benzene­carbothiolate, C₁₃H₉NO₃S (2) (monoclinic P2₁/a), the nitro group is rotated by 33.0 (2)° out of the plane of the adjacent aryl ring and the thiobenzoate group is strongly twisted away from the plane of the disubstituted aryl ring. The molecules of (2) are linked into chains by C—H...O hydrogen bonds, and each chain is linked to two neighbouring chains by means of aromatic π...π stacking interactions. In 1-(2-nitrophenylthio)-2,5-pyrrolidinedione, C₁₀H₈N₂O₄S (3) (monoclinic P2₁/a), the nitro group is again almost coplanar with the adjacent aryl ring, but the pyrrolidinedione unit is almost orthogonal to the O₂NC₆H₄SN plane. There are three types of C—H...O hydrogen bond in the structure, and these link the molecules into a two-dimensional net. The conformations of these molecules have been investigated by SCF calculations and two energy minima have been identified for each: the molecules of (1) and (3) adopt conformations in their crystals which are close to those at the overall energy minima calculated for isolated molecules, while molecules of (2) adopt a conformation in the crystal close to that calculated for the local energy minimum. Comparisons are made with the structures of some related compounds and it is concluded that, while the nature of the two conformational minima is determined by intramolecular forces, the choice between them is determined primarily by intermolecular forces.

Computing details

Data collection: CAD4 (Enraf-Nonius, 1992) for (1); CAD-4-PC Software (Enraf-Nonius, 1992) for (2), (3). Cell refinement: SET4 & CELDIM (Enraf-Nonius, 1992) for (1); SET4 & CELDIM in CAD-4-PC Software (Enraf-Nonius, 1992) for (2), (3). For all compounds, data reduction: DATRD2 in NRCVAX96 (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: NRCVAX96 and SHELXL97 (Sheldrick, 1997b); molecular graphics: NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998); software used to prepare material for publication: NRCVAX96, SHELXL97 and WORDPERFECT macro PREP8 (Ferguson, 1998).

(1) (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene

Crystal data

C15H13NO2S	? #Insert any comments here.
Mr = 271.32	Dx = 1.446 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 21.595 (3) Å	θ = 9.4–16.5°
b = 14.518 (2) Å	µ = 0.26 mm^−1
c = 7.9530 (7) Å	T = 293 K
V = 2493.4 (5) Å^3	Plate, colourless
Z = 8	0.42 × 0.29 × 0.08 mm
F(000) = 1136

Data collection

Enraf-Nonius CAD-4 diffractometer	1237 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.000
Graphite monochromator	θmax = 27.4°, θmin = 2.4°
θ/2θ scans	h = −28→0
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989)	k = 0→18
Tmin = 0.935, Tmax = 0.982	l = 0→10
2877 measured reflections	3 standard reflections every 120 min
2877 independent reflections	intensity decay: 0.1%

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0596P)^2] where P = (Fo^2 + 2Fc^2)/3
2877 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. ? #Insert any special details here.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	−0.02924 (15)	0.3370 (2)	0.2452 (5)	0.0378 (8)
S1	−0.09836 (4)	0.31829 (6)	0.13278 (15)	0.0520 (3)
C2	0.00810 (15)	0.2712 (2)	0.3100 (5)	0.0362 (9)
N2	−0.00862 (15)	0.18036 (19)	0.2840 (4)	0.0442 (8)
O1	−0.05522 (13)	0.16401 (15)	0.2033 (4)	0.0583 (8)
O2	0.02491 (12)	0.12512 (15)	0.3463 (4)	0.0669 (9)
C3	0.06125 (15)	0.2871 (2)	0.4004 (5)	0.0416 (9)
C4	0.08077 (16)	0.3707 (2)	0.4321 (5)	0.0444 (10)
C41	0.13784 (18)	0.3891 (3)	0.5349 (6)	0.0636 (12)
C5	0.04487 (16)	0.4362 (2)	0.3672 (5)	0.0459 (10)
C6	−0.00814 (16)	0.4202 (2)	0.2775 (5)	0.0470 (10)
C7	−0.12040 (18)	0.4236 (2)	0.0740 (5)	0.0546 (11)
C8	−0.17354 (17)	0.4563 (2)	0.1196 (5)	0.0504 (10)
C9	−0.20091 (16)	0.5384 (2)	0.0670 (5)	0.0396 (9)
C10	−0.17387 (16)	0.5929 (2)	−0.0516 (5)	0.0472 (10)
C11	−0.20234 (18)	0.6680 (2)	−0.0971 (6)	0.0562 (11)
C12	−0.2573 (2)	0.6928 (3)	−0.0244 (6)	0.0667 (13)
C13	−0.28447 (19)	0.6408 (3)	0.0921 (7)	0.0688 (14)
C14	−0.25635 (17)	0.5637 (3)	0.1374 (6)	0.0552 (10)
H3	0.0840	0.2372	0.4402	0.050*
H41A	0.1432	0.4544	0.5480	0.095*	0.50
H41B	0.1733	0.3637	0.4789	0.095*	0.50
H41C	0.1335	0.3611	0.6436	0.095*	0.50
H41D	0.1568	0.3317	0.5657	0.095*	0.50
H41E	0.1267	0.4224	0.6347	0.095*	0.50
H41F	0.1665	0.4250	0.4700	0.095*	0.50
H5	0.0566	0.4971	0.3839	0.055*
H6	−0.0303	0.4705	0.2374	0.056*
H7	−0.0942	0.4591	0.0078	0.065*
H8	−0.1960	0.4212	0.1960	0.060*
H10	−0.1360	0.5768	−0.0989	0.057*
H11	−0.1851	0.7053	−0.1800	0.067*
H12	−0.2762	0.7475	−0.0573	0.080*
H13	−0.3220	0.6581	0.1401	0.083*
H14	−0.2745	0.5261	0.2183	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0430 (19)	0.0295 (16)	0.041 (2)	−0.0021 (15)	0.0060 (18)	−0.0001 (16)
S1	0.0508 (5)	0.0339 (4)	0.0713 (7)	0.0003 (4)	−0.0052 (6)	0.0006 (5)
C2	0.0445 (19)	0.0238 (16)	0.040 (2)	−0.0035 (14)	0.0050 (18)	−0.0039 (15)
N2	0.0556 (19)	0.0236 (14)	0.053 (2)	0.0004 (15)	0.0059 (17)	−0.0034 (15)
O2	0.0816 (19)	0.0235 (12)	0.096 (2)	0.0080 (13)	−0.0129 (19)	0.0039 (15)
O1	0.0677 (18)	0.0281 (12)	0.079 (2)	−0.0090 (12)	−0.0111 (17)	−0.0016 (13)
C3	0.049 (2)	0.0266 (15)	0.049 (3)	0.0044 (14)	0.000 (2)	0.0020 (17)
C4	0.045 (2)	0.0369 (18)	0.051 (3)	−0.0043 (16)	0.0047 (19)	−0.0032 (19)
C41	0.063 (3)	0.047 (2)	0.080 (4)	−0.013 (2)	−0.010 (3)	−0.006 (2)
C5	0.055 (2)	0.0260 (16)	0.057 (3)	−0.0033 (16)	0.006 (2)	−0.0044 (19)
C6	0.055 (2)	0.0252 (17)	0.061 (3)	0.0024 (16)	0.002 (2)	0.0059 (18)
C7	0.056 (2)	0.0349 (18)	0.073 (3)	0.0029 (18)	−0.003 (2)	0.002 (2)
C8	0.052 (2)	0.0379 (18)	0.061 (3)	−0.0024 (17)	−0.004 (2)	0.001 (2)
C9	0.0402 (19)	0.0354 (17)	0.043 (2)	−0.0029 (15)	−0.0048 (19)	−0.0050 (17)
C10	0.041 (2)	0.044 (2)	0.057 (3)	0.0007 (17)	0.006 (2)	−0.008 (2)
C11	0.062 (2)	0.040 (2)	0.067 (3)	−0.0006 (18)	−0.004 (2)	0.005 (2)
C12	0.070 (3)	0.041 (2)	0.089 (4)	0.008 (2)	−0.014 (3)	0.002 (3)
C13	0.052 (2)	0.050 (2)	0.103 (4)	0.012 (2)	0.008 (3)	−0.005 (3)
C14	0.052 (2)	0.050 (2)	0.064 (3)	−0.0038 (18)	0.010 (2)	0.007 (2)

Geometric parameters (Å, º)

C1—C6	1.315 (4)	C4—C41	1.503 (5)
C1—C2	1.353 (4)	C5—C6	1.369 (5)
C1—S1	1.761 (4)	C7—C8	1.294 (5)
S1—C7	1.667 (4)	C8—C9	1.394 (5)
C2—C3	1.374 (5)	C9—C10	1.363 (5)
C2—N2	1.383 (4)	C9—C14	1.372 (5)
N2—O2	1.189 (4)	C10—C11	1.304 (5)
N2—O1	1.217 (4)	C11—C12	1.369 (5)
C3—C4	1.310 (4)	C12—C13	1.331 (6)
C4—C5	1.331 (5)	C13—C14	1.323 (5)
C6—C1—C2	111.6 (3)	C5—C4—C41	124.2 (3)
C6—C1—S1	122.3 (3)	C4—C5—C6	124.6 (3)
C2—C1—S1	126.1 (3)	C1—C6—C5	123.2 (3)
C7—S1—C1	104.0 (2)	C8—C7—S1	120.8 (3)
C1—C2—C3	125.3 (3)	C7—C8—C9	127.3 (4)
C1—C2—N2	117.5 (3)	C10—C9—C14	120.0 (3)
C3—C2—N2	117.2 (3)	C10—C9—C8	121.5 (3)
O2—N2—O1	126.3 (3)	C14—C9—C8	118.5 (4)
O2—N2—C2	115.0 (3)	C11—C10—C9	118.4 (4)
O1—N2—C2	118.7 (3)	C10—C11—C12	120.8 (4)
C4—C3—C2	121.7 (3)	C13—C12—C11	121.8 (4)
C3—C4—C5	113.6 (3)	C14—C13—C12	117.9 (4)
C3—C4—C41	122.2 (3)	C13—C14—C9	121.1 (4)
C6—C1—S1—C7	4.8 (4)	C2—C1—C6—C5	−0.5 (6)
C2—C1—S1—C7	−175.9 (3)	S1—C1—C6—C5	178.8 (3)
C6—C1—C2—C3	0.7 (5)	C4—C5—C6—C1	−0.3 (6)
S1—C1—C2—C3	−178.6 (3)	C1—S1—C7—C8	−121.0 (4)
C6—C1—C2—N2	−179.6 (3)	S1—C7—C8—C9	−172.9 (3)
S1—C1—C2—N2	1.1 (5)	C7—C8—C9—C10	3.7 (6)
C1—C2—N2—O2	−178.5 (3)	C7—C8—C9—C14	−176.4 (4)
C3—C2—N2—O2	1.2 (5)	C14—C9—C10—C11	−1.0 (6)
C1—C2—N2—O1	0.8 (5)	C8—C9—C10—C11	179.0 (4)
C3—C2—N2—O1	−179.4 (3)	C9—C10—C11—C12	1.7 (6)
C1—C2—C3—C4	0.0 (6)	C10—C11—C12—C13	−1.5 (7)
N2—C2—C3—C4	−179.8 (3)	C11—C12—C13—C14	0.5 (7)
C2—C3—C4—C5	−0.8 (6)	C12—C13—C14—C9	0.2 (7)
C2—C3—C4—C41	178.3 (4)	C10—C9—C14—C13	0.0 (6)
C3—C4—C5—C6	1.0 (6)	C8—C9—C14—C13	−179.9 (4)
C41—C4—C5—C6	−178.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	0.93	2.52	3.362 (4)	151
C6—H6···O2^i	0.93	2.34	3.155 (4)	146

Symmetry code: (i) −x, y+1/2, −z+1/2.

(2) S-(2-Nitrophenyl)benzenecarbothiolate

Crystal data

C13H9NO3S	F(000) = 536
Mr = 259.27	? #Insert any comments here.
Monoclinic, P21/a	Dx = 1.417 Mg m^−3
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 7.51 (5) Å	Cell parameters from 25 reflections
b = 21.16 (5) Å	θ = 9.6–16.9°
c = 7.66 (5) Å	µ = 0.27 mm^−1
β = 92.043 (10)°	T = 294 K
V = 1216 (12) Å^3	Block, yellow
Z = 4	0.42 × 0.24 × 0.24 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	1348 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.009
Graphite monochromator	θmax = 25.6°, θmin = 2.7°
θ/2θ scans	h = −9→9
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989)	k = 0→25
Tmin = 0.888, Tmax = 0.957	l = 0→9
2418 measured reflections	3 standard reflections every 180 min
2251 independent reflections	intensity decay: no decay, variation 1.0%

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 0.92	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2251 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. ? #Insert any special details here.

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

	x	y	z	Uiso*/Ueq
S1	0.94979 (10)	0.44016 (3)	0.23216 (13)	0.0817 (3)
C1	0.9948 (3)	0.36247 (12)	0.1614 (4)	0.0650 (8)
C2	0.9660 (3)	0.30717 (12)	0.2548 (4)	0.0583 (7)
N2	0.9052 (3)	0.30818 (11)	0.4359 (3)	0.0670 (6)
O1	0.9520 (3)	0.35152 (10)	0.5304 (3)	0.0893 (7)
O2	0.8108 (3)	0.26460 (9)	0.4848 (3)	0.0887 (7)
C3	0.9962 (4)	0.24843 (13)	0.1855 (4)	0.0673 (7)
C4	1.0613 (4)	0.24343 (16)	0.0212 (5)	0.0845 (9)
C5	1.0942 (5)	0.29693 (18)	−0.0758 (5)	0.0945 (11)
C6	1.0589 (4)	0.35540 (16)	−0.0052 (5)	0.0888 (10)
C7	0.7118 (3)	0.43836 (11)	0.2364 (4)	0.0582 (7)
O7	0.6316 (3)	0.39058 (9)	0.2062 (3)	0.0878 (7)
C8	0.6264 (3)	0.49974 (11)	0.2761 (3)	0.0560 (6)
C9	0.4514 (4)	0.50777 (14)	0.2278 (4)	0.0744 (8)
C10	0.3663 (5)	0.56457 (16)	0.2607 (5)	0.0880 (10)
C11	0.4597 (5)	0.61290 (14)	0.3407 (5)	0.0849 (10)
C12	0.6320 (5)	0.60466 (13)	0.3908 (5)	0.0844 (10)
C13	0.7179 (4)	0.54840 (12)	0.3574 (4)	0.0713 (8)
H3	0.9726	0.2123	0.2497	0.081*
H4	1.0835	0.2037	−0.0253	0.101*
H5	1.1394	0.2936	−0.1868	0.113*
H6	1.0788	0.3914	−0.0715	0.107*
H9	0.3887	0.4751	0.1726	0.089*
H10	0.2465	0.5698	0.2286	0.106*
H11	0.4040	0.6514	0.3604	0.102*
H12	0.6937	0.6371	0.4482	0.101*
H13	0.8376	0.5435	0.3900	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0648 (5)	0.0512 (4)	0.1287 (8)	−0.0005 (3)	−0.0022 (5)	0.0012 (4)
C1	0.0574 (15)	0.0589 (15)	0.078 (2)	0.0102 (12)	−0.0040 (15)	0.0086 (14)
C2	0.0544 (14)	0.0570 (14)	0.0630 (17)	0.0085 (12)	−0.0071 (13)	0.0032 (13)
N2	0.0652 (14)	0.0571 (13)	0.0782 (18)	0.0072 (11)	−0.0038 (12)	0.0039 (13)
O1	0.1003 (16)	0.0862 (14)	0.0812 (16)	−0.0117 (12)	−0.0001 (12)	−0.0206 (12)
O2	0.1063 (17)	0.0695 (12)	0.0909 (15)	−0.0053 (12)	0.0120 (13)	0.0131 (11)
C3	0.0730 (17)	0.0585 (16)	0.0698 (19)	0.0149 (13)	−0.0076 (15)	−0.0008 (14)
C4	0.094 (2)	0.0761 (19)	0.083 (2)	0.0266 (17)	−0.0106 (19)	−0.0106 (19)
C5	0.104 (3)	0.109 (3)	0.071 (2)	0.034 (2)	0.0007 (19)	−0.001 (2)
C6	0.094 (2)	0.086 (2)	0.086 (2)	0.0212 (18)	0.006 (2)	0.0275 (19)
C7	0.0642 (16)	0.0477 (13)	0.0626 (16)	−0.0034 (12)	0.0011 (13)	0.0056 (12)
O7	0.0729 (13)	0.0553 (11)	0.135 (2)	−0.0085 (10)	0.0025 (13)	−0.0186 (12)
C8	0.0604 (15)	0.0479 (13)	0.0598 (16)	−0.0016 (11)	0.0032 (12)	0.0088 (12)
C9	0.0718 (19)	0.0713 (18)	0.080 (2)	0.0023 (15)	0.0009 (16)	−0.0043 (16)
C10	0.077 (2)	0.092 (2)	0.095 (3)	0.0272 (18)	0.0080 (19)	0.0109 (19)
C11	0.104 (3)	0.0559 (17)	0.097 (2)	0.0162 (17)	0.033 (2)	0.0174 (17)
C12	0.094 (2)	0.0510 (16)	0.110 (3)	−0.0067 (15)	0.022 (2)	−0.0059 (16)
C13	0.0750 (18)	0.0522 (15)	0.087 (2)	−0.0047 (13)	0.0064 (16)	−0.0004 (14)

Geometric parameters (Å, º)

S1—C1	1.767 (5)	C5—C6	1.380 (5)
S1—C7	1.788 (12)	C7—O7	1.195 (4)
C1—C6	1.387 (9)	C7—C8	1.485 (5)
C1—C2	1.392 (5)	C8—C9	1.363 (9)
C2—C3	1.374 (5)	C8—C13	1.374 (5)
C2—N2	1.476 (9)	C9—C10	1.388 (5)
N2—O1	1.213 (4)	C10—C11	1.372 (6)
N2—O2	1.229 (4)	C11—C12	1.348 (9)
C3—C4	1.370 (9)	C12—C13	1.382 (5)
C4—C5	1.381 (6)
C1—S1—C7	100.8 (1)	C5—C6—C1	122.3 (3)
C6—C1—C2	116.6 (3)	O7—C7—C8	124.2 (4)
C6—C1—S1	117.3 (2)	O7—C7—S1	120.7 (3)
C2—C1—S1	126.1 (4)	C8—C7—S1	115.1 (2)
C3—C2—C1	122.1 (4)	C9—C8—C13	119.4 (3)
C3—C2—N2	115.9 (3)	C9—C8—C7	118.2 (3)
C1—C2—N2	122.0 (3)	C13—C8—C7	122.4 (4)
O1—N2—O2	122.9 (4)	C8—C9—C10	120.3 (3)
O1—N2—C2	118.7 (4)	C11—C10—C9	119.7 (5)
O2—N2—C2	118.5 (3)	C12—C11—C10	120.1 (3)
C4—C3—C2	119.6 (3)	C11—C12—C13	120.5 (3)
C3—C4—C5	120.5 (4)	C8—C13—C12	120.0 (4)
C4—C5—C6	118.9 (5)
C7—S1—C1—C6	110.6 (3)	S1—C1—C6—C5	−178.3 (3)
C7—S1—C1—C2	−66.9 (3)	C1—S1—C7—O7	4.4 (3)
C6—C1—C2—C3	−1.1 (4)	C1—S1—C7—C8	−174.6 (2)
S1—C1—C2—C3	176.5 (2)	O7—C7—C8—C9	−19.7 (5)
C6—C1—C2—N2	177.4 (2)	S1—C7—C8—C9	159.2 (3)
S1—C1—C2—N2	−5.0 (4)	O7—C7—C8—C13	161.0 (3)
C3—C2—N2—O1	146.4 (3)	S1—C7—C8—C13	−20.1 (4)
C1—C2—N2—O1	−32.2 (4)	C13—C8—C9—C10	−0.1 (4)
C3—C2—N2—O2	−32.8 (4)	C7—C8—C9—C10	−179.4 (3)
C1—C2—N2—O2	148.6 (3)	C8—C9—C10—C11	0.6 (5)
C1—C2—C3—C4	1.8 (4)	C9—C10—C11—C12	−1.6 (5)
N2—C2—C3—C4	−176.8 (2)	C10—C11—C12—C13	2.0 (5)
C2—C3—C4—C5	−0.9 (5)	C9—C8—C13—C12	0.5 (4)
C3—C4—C5—C6	−0.6 (5)	C7—C8—C13—C12	179.8 (3)
C4—C5—C6—C1	1.3 (5)	C11—C12—C13—C8	−1.5 (5)
C2—C1—C6—C5	−0.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O7^i	0.93	2.51	3.11 (2)	123

Symmetry code: (i) x+1/2, −y+1/2, z.

(3) 1-(2-Nitrophenylthio)-2,5-pyrrolidinedione

Crystal data

C10H8N2O4S	F(000) = 520
Mr = 252.24	? #Insert any comments here.
Monoclinic, P21/a	Dx = 1.568 Mg m^−3
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 7.918 (5) Å	Cell parameters from 25 reflections
b = 13.132 (5) Å	θ = 8.1–18.6°
c = 10.983 (5) Å	µ = 0.31 mm^−1
β = 110.7 (3)°	T = 294 K
V = 1068.5 (9) Å^3	Needle, yellow
Z = 4	0.42 × 0.15 × 0.11 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	1649 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.008
Graphite monochromator	θmax = 27.4°, θmin = 2.5°
θ/2θ scans	h = −10→9
Absorption correction: gaussian ABSO in NRCVAX (Gabe et al., 1989)	k = 0→17
Tmin = 0.951, Tmax = 0.970	l = 0→14
2733 measured reflections	3 standard reflections every 180 min
2452 independent reflections	intensity decay: no decay, variation 1.0%

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 0.86	w = 1/[σ^2(Fo^2) + (0.0972P)^2] where P = (Fo^2 + 2Fc^2)/3
2452 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. ? #Insert any special details here.

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

	x	y	z	Uiso*/Ueq
S1	0.14705 (6)	0.37939 (4)	0.26757 (4)	0.03763 (17)
C1	0.3739 (2)	0.37467 (12)	0.37446 (15)	0.0302 (3)
C2	0.4197 (2)	0.37267 (12)	0.50981 (16)	0.0326 (4)
N2	0.2778 (2)	0.37319 (12)	0.56487 (15)	0.0413 (4)
O1	0.12285 (19)	0.38200 (11)	0.48887 (14)	0.0541 (4)
O2	0.3164 (3)	0.36475 (14)	0.68166 (14)	0.0688 (5)
C3	0.5964 (3)	0.37222 (13)	0.59556 (18)	0.0413 (4)
C4	0.7344 (3)	0.37372 (14)	0.5464 (2)	0.0451 (5)
C5	0.6938 (3)	0.37287 (14)	0.4142 (2)	0.0446 (5)
C6	0.5179 (2)	0.37387 (13)	0.32930 (18)	0.0378 (4)
N7	0.1790 (2)	0.37435 (12)	0.12246 (14)	0.0399 (4)
C8	0.1569 (3)	0.28460 (17)	0.04812 (19)	0.0468 (5)
O8	0.1298 (3)	0.20288 (13)	0.08569 (15)	0.0765 (6)
C9	0.1689 (3)	0.31259 (18)	−0.08074 (18)	0.0548 (6)
C10	0.2216 (3)	0.42370 (19)	−0.0697 (2)	0.0580 (6)
C11	0.2049 (3)	0.46045 (17)	0.05538 (18)	0.0468 (5)
O11	0.2138 (2)	0.54553 (12)	0.09668 (14)	0.0667 (5)
H3	0.6217	0.3709	0.6849	0.050*
H4	0.8540	0.3753	0.6024	0.054*
H5	0.7871	0.3716	0.3813	0.054*
H6	0.4945	0.3740	0.2402	0.045*
H9A	0.0536	0.3025	−0.1501	0.066*
H9B	0.2592	0.2714	−0.0987	0.066*
H10A	0.3446	0.4316	−0.0673	0.070*
H10B	0.1418	0.4618	−0.1431	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0330 (2)	0.0497 (3)	0.0303 (2)	−0.0005 (2)	0.01139 (17)	−0.00009 (19)
C1	0.0335 (8)	0.0288 (8)	0.0293 (8)	−0.0002 (7)	0.0124 (6)	−0.0007 (6)
C2	0.0391 (9)	0.0300 (8)	0.0314 (8)	−0.0017 (7)	0.0157 (7)	−0.0008 (7)
N2	0.0511 (10)	0.0456 (9)	0.0339 (8)	−0.0080 (7)	0.0231 (7)	−0.0045 (6)
O1	0.0418 (8)	0.0773 (11)	0.0506 (8)	−0.0026 (7)	0.0258 (7)	−0.0028 (7)
O2	0.0852 (12)	0.0956 (13)	0.0360 (8)	−0.0137 (10)	0.0344 (8)	−0.0037 (8)
C3	0.0487 (11)	0.0371 (9)	0.0318 (9)	−0.0004 (8)	0.0066 (8)	−0.0002 (7)
C4	0.0353 (9)	0.0444 (11)	0.0474 (11)	0.0029 (9)	0.0044 (8)	−0.0009 (8)
C5	0.0332 (9)	0.0484 (11)	0.0549 (11)	0.0008 (8)	0.0187 (8)	−0.0041 (9)
C6	0.0365 (9)	0.0438 (10)	0.0361 (9)	0.0025 (8)	0.0163 (7)	−0.0028 (7)
N7	0.0435 (8)	0.0480 (9)	0.0265 (7)	−0.0019 (7)	0.0101 (6)	−0.0003 (6)
C8	0.0493 (11)	0.0549 (13)	0.0386 (10)	−0.0050 (10)	0.0184 (8)	−0.0063 (9)
O8	0.1260 (17)	0.0533 (10)	0.0663 (11)	−0.0186 (10)	0.0540 (11)	−0.0117 (8)
C9	0.0608 (13)	0.0716 (15)	0.0335 (10)	−0.0042 (12)	0.0183 (9)	−0.0064 (9)
C10	0.0671 (15)	0.0749 (15)	0.0359 (10)	0.0027 (12)	0.0230 (10)	0.0082 (10)
C11	0.0502 (11)	0.0547 (12)	0.0314 (9)	−0.0042 (10)	0.0093 (8)	0.0063 (8)
O11	0.0970 (13)	0.0511 (9)	0.0508 (9)	−0.0101 (9)	0.0248 (9)	0.0024 (7)

Geometric parameters (Å, º)

S1—N7	1.701 (2)	C4—C5	1.372 (3)
S1—C1	1.766 (6)	C5—C6	1.376 (5)
C1—C6	1.394 (3)	N7—C11	1.403 (3)
C1—C2	1.401 (3)	N7—C8	1.409 (3)
C2—C3	1.383 (5)	C8—O8	1.196 (3)
C2—N2	1.452 (3)	C8—C9	1.497 (3)
N2—O2	1.214 (3)	C9—C10	1.511 (4)
N2—O1	1.222 (5)	C10—C11	1.505 (3)
C3—C4	1.379 (4)	C11—O11	1.199 (3)
N7—S1—C1	99.7 (2)	C5—C6—C1	121.22 (18)
C6—C1—C2	116.0 (3)	C11—N7—C8	112.39 (17)
C6—C1—S1	122.07 (14)	C11—N7—S1	123.93 (14)
C2—C1—S1	121.9 (3)	C8—N7—S1	123.11 (14)
C3—C2—C1	123.0 (3)	O8—C8—N7	123.46 (19)
C3—C2—N2	117.49 (16)	O8—C8—C9	128.7 (2)
C1—C2—N2	119.5 (3)	N7—C8—C9	107.82 (18)
O2—N2—O1	123.2 (3)	C8—C9—C10	105.61 (18)
O2—N2—C2	119.8 (3)	C11—C10—C9	105.80 (19)
O1—N2—C2	117.01 (15)	O11—C11—N7	123.52 (19)
C4—C3—C2	118.93 (18)	O11—C11—C10	129.2 (2)
C3—C4—C5	119.5 (3)	N7—C11—C10	107.28 (19)
C6—C5—C4	121.3 (3)
N7—S1—C1—C6	3.36 (16)	S1—C1—C6—C5	178.28 (14)
N7—S1—C1—C2	−177.4 (1)	C1—S1—N7—C11	−88.61 (16)
C6—C1—C2—C3	1.4 (2)	C1—S1—N7—C8	100.7 (2)
S1—C1—C2—C3	−177.90 (13)	C11—N7—C8—O8	−178.6 (2)
C6—C1—C2—N2	−179.91 (16)	S1—N7—C8—O8	−6.9 (3)
S1—C1—C2—N2	0.8 (2)	C11—N7—C8—C9	0.0 (2)
C3—C2—N2—O2	−6.1 (2)	S1—N7—C8—C9	171.7 (1)
C1—C2—N2—O2	175.2 (2)	O8—C8—C9—C10	−175.0 (2)
C3—C2—N2—O1	174.17 (17)	N7—C8—C9—C10	6.5 (2)
C1—C2—N2—O1	−4.6 (2)	C8—C9—C10—C11	−10.1 (2)
C1—C2—C3—C4	−0.1 (3)	C8—N7—C11—O11	174.5 (2)
N2—C2—C3—C4	−178.75 (16)	S1—N7—C11—O11	3.0 (3)
C2—C3—C4—C5	−1.7 (3)	C8—N7—C11—C10	−6.5 (2)
C3—C4—C5—C6	2.1 (3)	S1—N7—C11—C10	−178.13 (14)
C4—C5—C6—C1	−0.7 (3)	C9—C10—C11—O11	−170.9 (2)
C2—C1—C6—C5	−1.0 (2)	C9—C10—C11—N7	10.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O11^i	0.93	2.54	3.355 (3)	147
C5—H5···O1^ii	0.93	2.50	3.203 (4)	132
C6—H6···O8^iii	0.93	2.52	3.261 (3)	137

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