2-(Benzoyl­methyl­sulfanyl)-6-methoxy-1H-benz­imidazole

The structure of the title compound, C₁₆H₁₄N₂O₂S, has been determined and shows a twisted mol­ecule with a dihedral angle of 66.31 (11) Å between the two aromatic ring systems. A single N—H...N association creates a slightly convoluted, linear hydrogen-bonded chain [graph set C₂²(4)] in the b-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.126
• Data-to-parameter ratio = 12.7

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   0.103
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO, SCALEPACK (Otwinowski & Minor, 1997) and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

2-(Benzoylmethylsulfanyl)-6-methoxy-1H-benzimidazole

Crystal data

C16H14N2O2S	F(000) = 624
Mr = 298.35	Dx = 1.432 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17502 reflections
a = 5.7681 (3) Å	θ = 2.9–27.5°
b = 9.8914 (6) Å	µ = 0.24 mm^−1
c = 24.4281 (16) Å	T = 120 K
β = 96.798 (3)°	Plate, colourless
V = 1383.94 (14) Å^3	0.26 × 0.14 × 0.02 mm
Z = 4

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2413 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	1676 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.103
Detector resolution: 9.091 pixels mm^-1	θmax = 25.0°, θmin = 3.3°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
Tmin = 0.941, Tmax = 0.987	l = −28→29
13373 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.5232P] where P = (Fo^2 + 2Fc^2)/3
2413 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Geometry. Mean plane data ex SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.2227 (0.0061) x + 2.9007 (0.0120) y + 17.2023 (0.0222) z = 5.8817 (0.0111)

* 0.0017 (0.0022) C4 * -0.0068 (0.0022) C5 * 0.0055 (0.0023) C6 * 0.0010 (0.0022) C7 * -0.0062 (0.0022) C8 * 0.0048 (0.0022) C9 - 0.0461 (0.0044) N1 - 0.0751 (0.0051) C2 - 0.0309 (0.0045) N3

Rms deviation of fitted atoms = 0.0049

- 1.9454 (0.0084) x + 8.1909 (0.0081) y + 11.8372 (0.0302) z = 5.9960 (0.0054)

Angle to previous plane (with approximate e.s.d.) = 66.31 (0.11)

* 0.0028 (0.0024) C24 * 0.0057 (0.0024) C25 * -0.0080 (0.0026) C26 * 0.0018 (0.0027) C27 * 0.0068 (0.0027) C28 * -0.0090 (0.0026) C29

Rms deviation of fitted atoms = 0.0063

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

	x	y	z	Uiso*/Ueq
N1	0.9325 (5)	0.5458 (3)	0.25983 (11)	0.0230 (7)
H1	0.9955	0.4646	0.2614	0.029*
C2	0.9931 (5)	0.6521 (3)	0.22888 (13)	0.0199 (8)
N3	0.8733 (4)	0.7623 (3)	0.23531 (11)	0.0227 (7)
C4	0.5409 (5)	0.7995 (3)	0.29319 (13)	0.0226 (8)
H4	0.5136	0.8914	0.2831	0.028*
C5	0.4086 (6)	0.7362 (3)	0.32816 (14)	0.0239 (8)
H5	0.2861	0.7847	0.3421	0.030*
C6	0.4492 (6)	0.6002 (3)	0.34422 (14)	0.0232 (8)
O61	0.3023 (4)	0.5542 (2)	0.38032 (9)	0.0323 (6)
C62	0.3342 (7)	0.4191 (4)	0.39969 (17)	0.0417 (10)
H61	0.2214	0.3992	0.4256	0.052*
H62	0.4931	0.4084	0.4184	0.052*
H63	0.3101	0.3565	0.3684	0.052*
C7	0.6218 (6)	0.5247 (3)	0.32434 (13)	0.0246 (8)
H7	0.6492	0.4330	0.3348	0.031*
C8	0.7536 (5)	0.5899 (3)	0.28824 (13)	0.0208 (8)
C9	0.7189 (6)	0.7250 (3)	0.27260 (13)	0.0217 (8)
S21	1.21906 (14)	0.64227 (8)	0.18672 (4)	0.0243 (3)
C22	1.1044 (5)	0.5142 (3)	0.13710 (13)	0.0231 (8)
H221	1.2251	0.4911	0.1130	0.029*
H222	1.0678	0.4313	0.1571	0.029*
C23	0.8872 (6)	0.5621 (3)	0.10198 (13)	0.0228 (8)
O23	0.6954 (4)	0.5361 (2)	0.11555 (10)	0.0325 (6)
C24	0.9109 (5)	0.6384 (3)	0.05037 (14)	0.0227 (8)
C25	0.7158 (6)	0.6491 (3)	0.01116 (14)	0.0277 (8)
H25	0.5735	0.6072	0.0177	0.035*
C26	0.7269 (6)	0.7199 (4)	−0.03720 (15)	0.0343 (9)
H26	0.5933	0.7249	−0.0639	0.043*
C27	0.9315 (6)	0.7838 (4)	−0.04693 (15)	0.0359 (10)
H27	0.9384	0.8336	−0.0800	0.045*
C28	1.1249 (6)	0.7746 (4)	−0.00836 (16)	0.0377 (10)
H28	1.2653	0.8189	−0.0147	0.047*
C29	1.1170 (6)	0.7014 (4)	0.03969 (15)	0.0327 (9)
H29	1.2530	0.6940	0.0656	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0267 (16)	0.0149 (15)	0.0269 (17)	0.0003 (12)	0.0013 (13)	−0.0006 (13)
C2	0.0210 (17)	0.0165 (19)	0.0217 (19)	−0.0001 (15)	0.0007 (15)	−0.0022 (15)
N3	0.0218 (15)	0.0182 (15)	0.0273 (17)	0.0003 (12)	0.0000 (13)	0.0007 (13)
C4	0.0238 (18)	0.0162 (17)	0.026 (2)	0.0027 (15)	−0.0041 (16)	−0.0021 (16)
C5	0.0221 (19)	0.0238 (19)	0.024 (2)	0.0021 (15)	−0.0032 (16)	−0.0029 (16)
C6	0.0221 (18)	0.026 (2)	0.021 (2)	−0.0016 (15)	0.0017 (15)	−0.0047 (16)
O61	0.0370 (15)	0.0295 (15)	0.0324 (15)	0.0016 (11)	0.0130 (12)	0.0021 (12)
C62	0.051 (3)	0.031 (2)	0.047 (3)	−0.0009 (19)	0.021 (2)	0.009 (2)
C7	0.0288 (19)	0.0207 (19)	0.023 (2)	−0.0025 (16)	−0.0012 (16)	0.0007 (16)
C8	0.0210 (18)	0.0207 (18)	0.0195 (19)	−0.0005 (14)	−0.0024 (15)	−0.0043 (16)
C9	0.0203 (18)	0.0201 (19)	0.023 (2)	−0.0018 (14)	−0.0056 (15)	−0.0026 (15)
S21	0.0225 (5)	0.0226 (5)	0.0278 (5)	−0.0033 (4)	0.0027 (4)	−0.0012 (4)
C22	0.0256 (18)	0.0212 (18)	0.022 (2)	−0.0010 (14)	0.0011 (15)	−0.0035 (15)
C23	0.0250 (19)	0.0187 (18)	0.024 (2)	−0.0006 (14)	0.0006 (16)	−0.0049 (16)
O23	0.0219 (14)	0.0382 (15)	0.0381 (16)	−0.0053 (11)	0.0065 (11)	0.0085 (12)
C24	0.0223 (18)	0.0224 (18)	0.023 (2)	0.0036 (15)	0.0028 (15)	−0.0011 (16)
C25	0.0239 (19)	0.033 (2)	0.026 (2)	0.0005 (16)	0.0009 (16)	0.0000 (18)
C26	0.031 (2)	0.043 (2)	0.026 (2)	0.0057 (18)	−0.0064 (17)	−0.0016 (19)
C27	0.035 (2)	0.044 (2)	0.029 (2)	0.0058 (18)	0.0067 (18)	0.0102 (19)
C28	0.027 (2)	0.046 (2)	0.041 (3)	−0.0016 (18)	0.0073 (19)	0.015 (2)
C29	0.024 (2)	0.041 (2)	0.033 (2)	0.0035 (17)	0.0019 (17)	0.0101 (19)

Geometric parameters (Å, º)

N1—C2	1.364 (4)	C8—C9	1.398 (5)
N1—C8	1.381 (4)	S21—C22	1.823 (3)
N1—H1	0.88	C22—C23	1.509 (4)
C2—N3	1.310 (4)	C22—H221	0.99
C2—S21	1.757 (3)	C22—H222	0.99
N3—C9	1.397 (4)	C23—O23	1.219 (4)
C4—C5	1.363 (5)	C23—C24	1.489 (5)
C4—C9	1.404 (5)	C24—C25	1.393 (4)
C4—H4	0.95	C24—C29	1.393 (5)
C5—C6	1.413 (5)	C25—C26	1.382 (5)
C5—H5	0.95	C25—H25	0.95
C6—O61	1.371 (4)	C26—C27	1.384 (5)
C6—C7	1.378 (5)	C26—H26	0.95
O61—C62	1.423 (4)	C27—C28	1.375 (5)
C62—H61	0.98	C27—H27	0.95
C62—H62	0.98	C28—C29	1.385 (5)
C62—H63	0.98	C28—H28	0.95
C7—C8	1.389 (5)	C29—H29	0.95
C7—H7	0.95
C2—N1—C8	106.9 (3)	N3—C9—C4	130.1 (3)
C2—N1—H1	126.5	C8—C9—C4	119.4 (3)
C8—N1—H1	126.5	C2—S21—C22	101.08 (15)
N3—C2—N1	113.7 (3)	C23—C22—S21	111.8 (2)
N3—C2—S21	123.7 (2)	C23—C22—H221	109.3
N1—C2—S21	122.6 (2)	S21—C22—H221	109.3
C2—N3—C9	104.1 (3)	C23—C22—H222	109.3
C5—C4—C9	118.1 (3)	S21—C22—H222	109.3
C5—C4—H4	121.0	H221—C22—H222	107.9
C9—C4—H4	121.0	O23—C23—C24	121.0 (3)
C4—C5—C6	121.7 (3)	O23—C23—C22	119.9 (3)
C4—C5—H5	119.2	C24—C23—C22	119.1 (3)
C6—C5—H5	119.2	C25—C24—C29	118.4 (3)
O61—C6—C7	125.0 (3)	C25—C24—C23	118.2 (3)
O61—C6—C5	113.6 (3)	C29—C24—C23	123.4 (3)
C7—C6—C5	121.4 (3)	C26—C25—C24	120.7 (3)
C6—O61—C62	117.4 (3)	C26—C25—H25	119.6
O61—C62—H61	109.5	C24—C25—H25	119.6
O61—C62—H62	109.5	C25—C26—C27	120.3 (3)
H61—C62—H62	109.5	C25—C26—H26	119.8
O61—C62—H63	109.5	C27—C26—H26	119.8
H61—C62—H63	109.5	C28—C27—C26	119.4 (4)
H62—C62—H63	109.5	C28—C27—H27	120.3
C6—C7—C8	116.4 (3)	C26—C27—H27	120.3
C6—C7—H7	121.8	C27—C28—C29	120.7 (3)
C8—C7—H7	121.8	C27—C28—H28	119.7
N1—C8—C7	132.1 (3)	C29—C28—H28	119.7
N1—C8—C9	104.8 (3)	C28—C29—C24	120.5 (3)
C7—C8—C9	123.1 (3)	C28—C29—H29	119.8
N3—C9—C8	110.4 (3)	C24—C29—H29	119.8
C8—N1—C2—N3	1.3 (4)	C7—C8—C9—C4	−1.0 (5)
C8—N1—C2—S21	178.8 (2)	C5—C4—C9—N3	177.6 (3)
N1—C2—N3—C9	−1.1 (4)	C5—C4—C9—C8	0.2 (5)
S21—C2—N3—C9	−178.7 (2)	N3—C2—S21—C22	−119.0 (3)
C9—C4—C5—C6	0.9 (5)	N1—C2—S21—C22	63.6 (3)
C4—C5—C6—O61	178.8 (3)	C2—S21—C22—C23	65.4 (3)
C4—C5—C6—C7	−1.2 (5)	S21—C22—C23—O23	−93.6 (3)
C7—C6—O61—C62	1.5 (5)	S21—C22—C23—C24	87.7 (3)
C5—C6—O61—C62	−178.6 (3)	O23—C23—C24—C25	−16.3 (5)
O61—C6—C7—C8	−179.6 (3)	C22—C23—C24—C25	162.4 (3)
C5—C6—C7—C8	0.5 (5)	O23—C23—C24—C29	162.7 (3)
C2—N1—C8—C7	178.1 (3)	C22—C23—C24—C29	−18.6 (5)
C2—N1—C8—C9	−0.8 (3)	C29—C24—C25—C26	0.2 (5)
C6—C7—C8—N1	−178.1 (3)	C23—C24—C25—C26	179.3 (3)
C6—C7—C8—C9	0.7 (5)	C24—C25—C26—C27	−1.3 (5)
C2—N3—C9—C8	0.6 (3)	C25—C26—C27—C28	0.9 (6)
C2—N3—C9—C4	−177.0 (3)	C26—C27—C28—C29	0.5 (6)
N1—C8—C9—N3	0.1 (3)	C27—C28—C29—C24	−1.6 (6)
C7—C8—C9—N3	−178.9 (3)	C25—C24—C29—C28	1.2 (5)
N1—C8—C9—C4	178.0 (3)	C23—C24—C29—C28	−177.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3^i	0.88	2.14	3.017 (4)	176

Symmetry code: (i) −x+2, y−1/2, −z+1/2.