1-(4-Methyl­phenyl­sulfon­yl)-5-nitro-1H-benzimidazole

In the title compound, C₁₇H₁₅N₃O₄S, the mean plane of the benzimidazole fragment and the benzene ring of the p-tosyl group make a dihedral angle of 86.72 (14)°. The mol­ecules are linked by weak C—H...O inter­molecular hydrogen bonds into chains parallel to the b axis. The crystal packing is further stabilized by π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.059
• wR factor = 0.158
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       2.00 Sigma

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O3      ..       5.22 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 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
   1 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: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1-(4-Methylphenylsulfonyl)-5-nitro-1H-benzimidazole

Crystal data

C14H11N3O4S	F(000) = 656
Mr = 317.32	Dx = 1.507 Mg m^−3
Monoclinic, P21/n	Melting point: 446 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.630 (3) Å	Cell parameters from 3394 reflections
b = 9.950 (3) Å	θ = 2.5–25.0°
c = 13.662 (4) Å	µ = 0.25 mm^−1
β = 104.577 (4)°	T = 298 K
V = 1398.5 (7) Å^3	Block, colourless
Z = 4	0.29 × 0.24 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2453 independent reflections
Radiation source: fine-focus sealed tube	1871 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 83.66 pixels mm^-1	θmax = 25.0°, θmin = 2.5°
ω scans	h = −7→12
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −11→11
Tmin = 0.929, Tmax = 0.953	l = −16→16
6561 measured reflections

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)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.158	w = 1/[σ^2(Fo^2) + (0.0583P)^2 + 1.2495P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2453 reflections	Δρmax = 0.19 e Å^−3
201 parameters	Δρmin = −0.32 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: 0.0012 (6)

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
S1	0.34069 (9)	0.17986 (10)	0.14269 (7)	0.0594 (3)
O1	0.6110 (4)	−0.5076 (3)	0.1383 (4)	0.1256 (15)
O2	0.7927 (3)	−0.4150 (3)	0.1349 (2)	0.0834 (9)
O3	0.3426 (3)	0.3106 (3)	0.1007 (2)	0.0762 (8)
O4	0.2374 (2)	0.0882 (3)	0.1042 (2)	0.0736 (8)
N1	0.6870 (3)	0.0856 (3)	0.1290 (2)	0.0602 (8)
N2	0.4745 (3)	0.1035 (3)	0.1265 (2)	0.0497 (7)
N3	0.6780 (4)	−0.4096 (3)	0.1354 (3)	0.0722 (9)
C1	0.5021 (3)	−0.0351 (3)	0.1308 (2)	0.0472 (7)
C2	0.4270 (3)	−0.1482 (3)	0.1317 (3)	0.0568 (9)
H2A	0.3395	−0.1419	0.1311	0.068*
C3	0.4874 (4)	−0.2705 (4)	0.1334 (3)	0.0602 (9)
H3	0.4404	−0.3494	0.1329	0.072*
C4	0.6181 (4)	−0.2762 (3)	0.1358 (2)	0.0537 (8)
C5	0.6935 (3)	−0.1658 (3)	0.1334 (2)	0.0521 (8)
H5	0.7806	−0.1730	0.1329	0.063*
C6	0.6327 (3)	−0.0421 (3)	0.1316 (2)	0.0476 (7)
C7	0.5917 (4)	0.1677 (4)	0.1265 (3)	0.0588 (9)
H7A	0.6003	0.2606	0.1249	0.071*
C8	0.3688 (3)	0.1923 (3)	0.2734 (3)	0.0517 (8)
C9	0.4334 (3)	0.3033 (3)	0.3227 (3)	0.0565 (9)
H9	0.4586	0.3724	0.2860	0.068*
C10	0.4601 (3)	0.3108 (4)	0.4264 (3)	0.0590 (9)
H10	0.5047	0.3850	0.4595	0.071*
C11	0.4215 (3)	0.2092 (4)	0.4828 (3)	0.0566 (9)
C12	0.3558 (3)	0.0998 (4)	0.4318 (3)	0.0611 (9)
H12	0.3293	0.0313	0.4684	0.073*
C13	0.3288 (3)	0.0900 (4)	0.3279 (3)	0.0610 (9)
H13	0.2843	0.0158	0.2947	0.073*
C14	0.4501 (4)	0.2193 (5)	0.5957 (3)	0.0752 (12)
H14A	0.4023	0.2932	0.6138	0.113*
H14B	0.5415	0.2340	0.6230	0.113*
H14C	0.4248	0.1374	0.6226	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0607 (6)	0.0566 (6)	0.0564 (5)	0.0152 (4)	0.0064 (4)	−0.0031 (4)
O1	0.116 (3)	0.0402 (17)	0.207 (4)	−0.0010 (18)	0.017 (3)	−0.003 (2)
O2	0.092 (2)	0.074 (2)	0.087 (2)	0.0326 (17)	0.0283 (17)	0.0040 (15)
O3	0.105 (2)	0.0538 (15)	0.0653 (16)	0.0292 (14)	0.0129 (15)	0.0121 (12)
O4	0.0575 (15)	0.0785 (18)	0.0754 (17)	0.0056 (13)	−0.0011 (12)	−0.0188 (14)
N1	0.0621 (18)	0.0472 (17)	0.074 (2)	−0.0057 (14)	0.0231 (15)	0.0000 (14)
N2	0.0524 (16)	0.0413 (15)	0.0555 (16)	0.0051 (12)	0.0138 (12)	−0.0014 (12)
N3	0.090 (3)	0.0476 (19)	0.074 (2)	0.0089 (18)	0.0123 (19)	−0.0021 (15)
C1	0.0525 (18)	0.0432 (17)	0.0442 (17)	0.0011 (14)	0.0089 (14)	−0.0001 (13)
C2	0.053 (2)	0.051 (2)	0.068 (2)	−0.0048 (16)	0.0169 (16)	−0.0040 (16)
C3	0.068 (2)	0.0421 (19)	0.070 (2)	−0.0094 (16)	0.0157 (18)	−0.0020 (16)
C4	0.065 (2)	0.0437 (18)	0.0502 (19)	0.0041 (16)	0.0113 (16)	0.0014 (14)
C5	0.0508 (19)	0.051 (2)	0.0540 (19)	0.0034 (15)	0.0120 (15)	0.0013 (15)
C6	0.0511 (18)	0.0437 (18)	0.0485 (17)	−0.0022 (14)	0.0135 (14)	0.0000 (14)
C7	0.074 (2)	0.0419 (19)	0.062 (2)	−0.0082 (17)	0.0200 (18)	0.0003 (15)
C8	0.0492 (18)	0.0480 (19)	0.0566 (19)	0.0080 (15)	0.0108 (15)	−0.0048 (15)
C9	0.059 (2)	0.049 (2)	0.064 (2)	0.0002 (16)	0.0187 (17)	−0.0032 (16)
C10	0.057 (2)	0.054 (2)	0.064 (2)	−0.0021 (16)	0.0114 (17)	−0.0099 (17)
C11	0.0503 (19)	0.061 (2)	0.061 (2)	0.0111 (16)	0.0188 (16)	−0.0022 (17)
C12	0.061 (2)	0.057 (2)	0.067 (2)	−0.0003 (17)	0.0207 (18)	0.0035 (17)
C13	0.059 (2)	0.053 (2)	0.071 (2)	−0.0041 (17)	0.0171 (18)	−0.0085 (17)
C14	0.069 (3)	0.095 (3)	0.065 (2)	0.003 (2)	0.023 (2)	−0.008 (2)

Geometric parameters (Å, º)

S1—O4	1.423 (3)	C5—C6	1.388 (4)
S1—O3	1.424 (3)	C5—H5	0.9300
S1—N2	1.676 (3)	C7—H7A	0.9300
S1—C8	1.739 (3)	C8—C9	1.382 (5)
O1—N3	1.213 (5)	C8—C13	1.391 (5)
O2—N3	1.222 (4)	C9—C10	1.375 (5)
N1—C7	1.295 (5)	C9—H9	0.9300
N1—C6	1.400 (4)	C10—C11	1.394 (5)
N2—C7	1.399 (4)	C10—H10	0.9300
N2—C1	1.408 (4)	C11—C12	1.383 (5)
N3—C4	1.473 (5)	C11—C14	1.499 (5)
C1—C2	1.382 (5)	C12—C13	1.379 (5)
C1—C6	1.387 (4)	C12—H12	0.9300
C2—C3	1.372 (5)	C13—H13	0.9300
C2—H2A	0.9300	C14—H14A	0.9600
C3—C4	1.383 (5)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—C5	1.365 (5)
O4—S1—O3	121.63 (18)	C1—C6—N1	111.8 (3)
O4—S1—N2	105.22 (15)	C5—C6—N1	127.7 (3)
O3—S1—N2	105.19 (16)	N1—C7—N2	113.7 (3)
O4—S1—C8	110.05 (17)	N1—C7—H7A	123.1
O3—S1—C8	109.42 (16)	N2—C7—H7A	123.1
N2—S1—C8	103.62 (14)	C9—C8—C13	120.3 (3)
C7—N1—C6	104.4 (3)	C9—C8—S1	119.6 (3)
C7—N2—C1	105.7 (3)	C13—C8—S1	120.1 (3)
C7—N2—S1	125.3 (2)	C10—C9—C8	119.6 (3)
C1—N2—S1	127.8 (2)	C10—C9—H9	120.2
O1—N3—O2	124.0 (4)	C8—C9—H9	120.2
O1—N3—C4	117.8 (4)	C9—C10—C11	121.1 (3)
O2—N3—C4	118.2 (3)	C9—C10—H10	119.5
C2—C1—C6	122.5 (3)	C11—C10—H10	119.5
C2—C1—N2	133.2 (3)	C12—C11—C10	118.3 (3)
C6—C1—N2	104.3 (3)	C12—C11—C14	121.2 (4)
C3—C2—C1	117.0 (3)	C10—C11—C14	120.5 (3)
C3—C2—H2A	121.5	C13—C12—C11	121.5 (3)
C1—C2—H2A	121.5	C13—C12—H12	119.2
C2—C3—C4	120.0 (3)	C11—C12—H12	119.2
C2—C3—H3	120.0	C12—C13—C8	119.1 (3)
C4—C3—H3	120.0	C12—C13—H13	120.4
C5—C4—C3	124.0 (3)	C8—C13—H13	120.4
C5—C4—N3	117.9 (3)	C11—C14—H14A	109.5
C3—C4—N3	118.0 (3)	C11—C14—H14B	109.5
C4—C5—C6	116.1 (3)	H14A—C14—H14B	109.5
C4—C5—H5	122.0	C11—C14—H14C	109.5
C6—C5—H5	122.0	H14A—C14—H14C	109.5
C1—C6—C5	120.4 (3)	H14B—C14—H14C	109.5
O4—S1—N2—C7	161.1 (3)	N2—C1—C6—N1	0.6 (4)
O3—S1—N2—C7	31.5 (3)	C4—C5—C6—C1	−1.0 (5)
C8—S1—N2—C7	−83.3 (3)	C4—C5—C6—N1	−180.0 (3)
O4—S1—N2—C1	−32.9 (3)	C7—N1—C6—C1	−0.1 (4)
O3—S1—N2—C1	−162.4 (3)	C7—N1—C6—C5	179.0 (3)
C8—S1—N2—C1	82.7 (3)	C6—N1—C7—N2	−0.4 (4)
C7—N2—C1—C2	−179.1 (4)	C1—N2—C7—N1	0.8 (4)
S1—N2—C1—C2	12.7 (5)	S1—N2—C7—N1	169.4 (2)
C7—N2—C1—C6	−0.8 (3)	O4—S1—C8—C9	−159.5 (3)
S1—N2—C1—C6	−169.0 (2)	O3—S1—C8—C9	−23.4 (3)
C6—C1—C2—C3	0.0 (5)	N2—S1—C8—C9	88.4 (3)
N2—C1—C2—C3	178.1 (3)	O4—S1—C8—C13	21.7 (3)
C1—C2—C3—C4	1.0 (5)	O3—S1—C8—C13	157.9 (3)
C2—C3—C4—C5	−2.1 (6)	N2—S1—C8—C13	−90.4 (3)
C2—C3—C4—N3	−178.7 (3)	C13—C8—C9—C10	1.2 (5)
O1—N3—C4—C5	179.5 (4)	S1—C8—C9—C10	−177.5 (3)
O2—N3—C4—C5	1.4 (5)	C8—C9—C10—C11	−0.9 (5)
O1—N3—C4—C3	−3.7 (5)	C9—C10—C11—C12	0.2 (5)
O2—N3—C4—C3	178.2 (3)	C9—C10—C11—C14	−179.4 (3)
C3—C4—C5—C6	2.1 (5)	C10—C11—C12—C13	0.2 (5)
N3—C4—C5—C6	178.7 (3)	C14—C11—C12—C13	179.8 (3)
C2—C1—C6—C5	0.0 (5)	C11—C12—C13—C8	0.1 (5)
N2—C1—C6—C5	−178.6 (3)	C9—C8—C13—C12	−0.8 (5)
C2—C1—C6—N1	179.1 (3)	S1—C8—C13—C12	177.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4	0.93	2.52	3.059 (4)	117
C9—H9···O3	0.93	2.60	2.943 (5)	103
C7—H7A···O1^i	0.93	2.31	3.239 (5)	173
C2—H2A···Cg3^ii	0.93	2.92	3.708 (4)	144

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