Methyl 1-n-butyl-2-(3,4-di­chloro­phenyl)-1H-benz­imidazole-5-carboxyl­ate

A new benz­imidazole compound, methyl 1-n-butyl-2-(3,4-di­chloro­phenyl)-1H-benz­imidazole-5-carboxyl­ate, C₁₉H₁₈Cl₂N₂O₂, has been synthesized by the condensation of methyl 3-amino-4-(n-butyl­amino)­benzoate with an Na₂S₂O₅ adduct of 3,4-di­chloro­benz­aldehyde. The mol­ecule is twisted with a C—C—C—N torsion angle of −39.7 (3)° between the phenyl and benzimidazole groups. In the crystal structure, symmetry-related mol­ecules are linked by C—H...O interactions, forming a chain.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.117
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl ....    - p 2yn
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 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: X-AREA (Stoe & Cie, 1996); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Methyl 1-n-butyl-2-(3,4-dichlorophenyl)-1H-benzimidazole-5-carboxylate

Crystal data

C19H18Cl2N2O2	F(000) = 784
Mr = 377.25	Dx = 1.364 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: - P 2yn	Cell parameters from 15013 reflections
a = 9.3359 (6) Å	θ = 1.5–29.0°
b = 14.4051 (8) Å	µ = 0.37 mm^−1
c = 16.3707 (11) Å	T = 293 K
β = 123.459 (4)°	Prismatic, colourless
V = 1836.8 (2) Å^3	0.50 × 0.30 × 0.10 mm
Z = 4

Data collection

Stoe 2-circle goniometer diffractometer	2727 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.088
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
Detector resolution: 6.67 pixels mm^-1	h = −12→12
rotation method scans	k = −18→18
30007 measured reflections	l = −21→21
4133 independent 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)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.0182P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4133 reflections	Δρmax = 0.29 e Å^−3
227 parameters	Δρmin = −0.29 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: 0.0164 (18)

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
Cl1	1.28712 (9)	0.80832 (4)	0.66360 (6)	0.0989 (3)
Cl2	1.20564 (9)	0.72642 (5)	0.81258 (5)	0.0954 (3)
N2	0.85449 (18)	0.42999 (10)	0.62623 (10)	0.0492 (3)
N1	0.65298 (17)	0.46732 (9)	0.46999 (10)	0.0465 (3)
O1	0.67609 (19)	0.11285 (10)	0.69764 (10)	0.0691 (4)
O2	0.44064 (18)	0.08108 (9)	0.55246 (10)	0.0671 (4)
C1	1.1343 (3)	0.72266 (13)	0.62725 (17)	0.0628 (5)
C2	1.0485 (3)	0.68826 (13)	0.53337 (17)	0.0623 (5)
H2	1.0673	0.7143	0.4881	0.075*
C3	0.9346 (2)	0.61533 (13)	0.50577 (14)	0.0547 (4)
H3	0.8770	0.5927	0.4420	0.066*
C4	0.9057 (2)	0.57566 (12)	0.57276 (13)	0.0475 (4)
C5	0.9891 (2)	0.61276 (13)	0.66627 (14)	0.0553 (4)
H5	0.9682	0.5880	0.7112	0.066*
C6	1.1019 (3)	0.68550 (13)	0.69378 (16)	0.0624 (5)
C7	0.8044 (2)	0.49135 (11)	0.55597 (12)	0.0460 (4)
C8	0.6044 (2)	0.38289 (12)	0.48794 (12)	0.0457 (4)
C9	0.7311 (2)	0.36112 (12)	0.58523 (11)	0.0451 (4)
C10	0.7202 (2)	0.27947 (12)	0.62645 (12)	0.0484 (4)
H10	0.8044	0.2638	0.6908	0.058*
C11	0.5808 (2)	0.22214 (12)	0.56925 (12)	0.0482 (4)
C12	0.4528 (2)	0.24672 (13)	0.47210 (13)	0.0539 (4)
H12	0.3591	0.2075	0.4355	0.065*
C13	0.4623 (2)	0.32675 (13)	0.42992 (13)	0.0530 (4)
H13	0.3778	0.3426	0.3657	0.064*
C14	0.5549 (2)	0.51758 (13)	0.37755 (13)	0.0520 (4)
H14A	0.5885	0.5824	0.3890	0.062*
H14B	0.4338	0.5143	0.3531	0.062*
C15	0.5816 (3)	0.47927 (14)	0.30053 (13)	0.0579 (5)
H15A	0.7030	0.4813	0.3256	0.069*
H15B	0.5457	0.4148	0.2881	0.069*
C16	0.4831 (3)	0.53237 (17)	0.20534 (15)	0.0741 (6)
H16A	0.5197	0.5967	0.2174	0.089*
H16B	0.3617	0.5308	0.1803	0.089*
C17	0.5100 (5)	0.4927 (2)	0.12888 (19)	0.1131 (10)
H17C	0.4450	0.5282	0.0696	0.170*
H17B	0.4722	0.4293	0.1159	0.170*
H17A	0.6296	0.4955	0.1527	0.170*
C18	0.5735 (2)	0.13495 (13)	0.61444 (13)	0.0511 (4)
C19	0.4281 (3)	−0.00616 (15)	0.59155 (18)	0.0766 (6)
H19A	0.3288	−0.0394	0.5416	0.115*
H19B	0.4178	0.0054	0.6459	0.115*
H19C	0.5292	−0.0424	0.6132	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0903 (4)	0.0663 (4)	0.1471 (7)	−0.0239 (3)	0.0699 (5)	−0.0026 (4)
Cl2	0.1080 (5)	0.0814 (4)	0.0769 (4)	−0.0321 (3)	0.0384 (4)	−0.0254 (3)
N2	0.0494 (8)	0.0505 (8)	0.0434 (7)	−0.0028 (6)	0.0228 (7)	0.0021 (6)
N1	0.0474 (7)	0.0488 (8)	0.0411 (7)	0.0038 (6)	0.0230 (6)	0.0044 (6)
O1	0.0735 (9)	0.0667 (9)	0.0523 (8)	−0.0140 (7)	0.0253 (7)	0.0074 (6)
O2	0.0740 (9)	0.0629 (8)	0.0553 (8)	−0.0225 (7)	0.0299 (7)	−0.0030 (6)
C1	0.0610 (11)	0.0469 (10)	0.0867 (15)	0.0009 (8)	0.0445 (11)	0.0064 (10)
C2	0.0681 (11)	0.0554 (11)	0.0793 (14)	0.0102 (9)	0.0507 (11)	0.0187 (10)
C3	0.0559 (10)	0.0566 (11)	0.0549 (10)	0.0060 (8)	0.0326 (9)	0.0073 (8)
C4	0.0469 (9)	0.0477 (9)	0.0498 (9)	0.0029 (7)	0.0278 (8)	0.0026 (7)
C5	0.0610 (11)	0.0530 (10)	0.0550 (10)	−0.0037 (8)	0.0339 (9)	0.0003 (8)
C6	0.0613 (11)	0.0529 (11)	0.0672 (12)	−0.0042 (9)	0.0318 (10)	−0.0043 (9)
C7	0.0458 (9)	0.0483 (9)	0.0436 (9)	0.0018 (7)	0.0246 (8)	0.0003 (7)
C8	0.0459 (8)	0.0482 (9)	0.0424 (8)	0.0029 (7)	0.0241 (7)	0.0014 (7)
C9	0.0436 (8)	0.0489 (9)	0.0395 (8)	−0.0007 (7)	0.0209 (7)	−0.0005 (7)
C10	0.0488 (9)	0.0514 (10)	0.0410 (8)	−0.0012 (7)	0.0222 (8)	0.0013 (7)
C11	0.0489 (9)	0.0504 (10)	0.0442 (9)	−0.0012 (7)	0.0250 (8)	−0.0008 (7)
C12	0.0502 (9)	0.0570 (10)	0.0488 (9)	−0.0078 (8)	0.0238 (8)	−0.0052 (8)
C13	0.0464 (9)	0.0597 (11)	0.0409 (9)	0.0004 (8)	0.0165 (7)	0.0013 (8)
C14	0.0490 (9)	0.0559 (10)	0.0467 (9)	0.0087 (8)	0.0236 (8)	0.0094 (8)
C15	0.0553 (10)	0.0690 (12)	0.0446 (9)	0.0024 (9)	0.0246 (8)	0.0033 (8)
C16	0.0737 (14)	0.0888 (16)	0.0514 (11)	−0.0068 (11)	0.0292 (11)	0.0134 (10)
C17	0.121 (2)	0.164 (3)	0.0573 (15)	−0.016 (2)	0.0506 (16)	−0.0007 (16)
C18	0.0548 (10)	0.0541 (10)	0.0479 (10)	−0.0064 (8)	0.0306 (9)	−0.0037 (8)
C19	0.0963 (17)	0.0620 (13)	0.0733 (14)	−0.0272 (11)	0.0480 (13)	−0.0057 (10)

Geometric parameters (Å, º)

Cl1—C1	1.725 (2)	C10—C11	1.381 (2)
Cl2—C6	1.729 (2)	C10—H10	0.9300
N2—C7	1.315 (2)	C11—C12	1.410 (2)
N2—C9	1.382 (2)	C11—C18	1.478 (3)
N1—C7	1.380 (2)	C12—C13	1.372 (3)
N1—C8	1.385 (2)	C12—H12	0.9300
N1—C14	1.458 (2)	C13—H13	0.9300
O1—C18	1.198 (2)	C14—C15	1.518 (3)
O2—C18	1.335 (2)	C14—H14A	0.9700
O2—C19	1.444 (2)	C14—H14B	0.9700
C1—C2	1.375 (3)	C15—C16	1.510 (3)
C1—C6	1.389 (3)	C15—H15A	0.9700
C2—C3	1.382 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—C17	1.517 (4)
C3—C4	1.388 (2)	C16—H16A	0.9700
C3—H3	0.9300	C16—H16B	0.9700
C4—C5	1.386 (2)	C17—H17C	0.9600
C4—C7	1.469 (2)	C17—H17B	0.9600
C5—C6	1.374 (3)	C17—H17A	0.9600
C5—H5	0.9300	C19—H19A	0.9600
C8—C13	1.388 (2)	C19—H19B	0.9600
C8—C9	1.399 (2)	C19—H19C	0.9600
C9—C10	1.387 (2)
C7—N2—C9	104.98 (14)	C13—C12—H12	119.0
C7—N1—C8	105.96 (13)	C11—C12—H12	119.0
C7—N1—C14	129.65 (15)	C12—C13—C8	116.62 (16)
C8—N1—C14	124.38 (14)	C12—C13—H13	121.7
C18—O2—C19	115.94 (16)	C8—C13—H13	121.7
C2—C1—C6	119.53 (18)	N1—C14—C15	112.65 (15)
C2—C1—Cl1	120.31 (17)	N1—C14—H14A	109.1
C6—C1—Cl1	120.11 (18)	C15—C14—H14A	109.1
C1—C2—C3	120.56 (18)	N1—C14—H14B	109.1
C1—C2—H2	119.7	C15—C14—H14B	109.1
C3—C2—H2	119.7	H14A—C14—H14B	107.8
C2—C3—C4	120.27 (19)	C16—C15—C14	112.83 (17)
C2—C3—H3	119.9	C16—C15—H15A	109.0
C4—C3—H3	119.9	C14—C15—H15A	109.0
C5—C4—C3	118.60 (17)	C16—C15—H15B	109.0
C5—C4—C7	115.90 (15)	C14—C15—H15B	109.0
C3—C4—C7	125.28 (16)	H15A—C15—H15B	107.8
C6—C5—C4	121.21 (18)	C15—C16—C17	112.2 (2)
C6—C5—H5	119.4	C15—C16—H16A	109.2
C4—C5—H5	119.4	C17—C16—H16A	109.2
C5—C6—C1	119.8 (2)	C15—C16—H16B	109.2
C5—C6—Cl2	118.79 (17)	C17—C16—H16B	109.2
C1—C6—Cl2	121.42 (16)	H16A—C16—H16B	107.9
N2—C7—N1	113.18 (15)	C16—C17—H17C	109.5
N2—C7—C4	120.67 (15)	C16—C17—H17B	109.5
N1—C7—C4	126.15 (15)	H17C—C17—H17B	109.5
N1—C8—C13	131.88 (15)	C16—C17—H17A	109.5
N1—C8—C9	105.58 (14)	H17C—C17—H17A	109.5
C13—C8—C9	122.50 (16)	H17B—C17—H17A	109.5
N2—C9—C10	129.60 (15)	O1—C18—O2	122.35 (17)
N2—C9—C8	110.30 (14)	O1—C18—C11	124.48 (16)
C10—C9—C8	120.10 (15)	O2—C18—C11	113.17 (15)
C11—C10—C9	118.11 (15)	O2—C19—H19A	109.5
C11—C10—H10	120.9	O2—C19—H19B	109.5
C9—C10—H10	120.9	H19A—C19—H19B	109.5
C10—C11—C12	120.69 (16)	O2—C19—H19C	109.5
C10—C11—C18	117.05 (15)	H19A—C19—H19C	109.5
C12—C11—C18	122.25 (16)	H19B—C19—H19C	109.5
C13—C12—C11	121.95 (16)
C6—C1—C2—C3	−2.0 (3)	C14—N1—C8—C9	−178.45 (15)
Cl1—C1—C2—C3	175.56 (14)	C7—N2—C9—C10	179.65 (18)
C1—C2—C3—C4	−0.2 (3)	C7—N2—C9—C8	−0.13 (19)
C2—C3—C4—C5	2.1 (3)	N1—C8—C9—N2	−0.10 (18)
C2—C3—C4—C7	−172.29 (17)	C13—C8—C9—N2	−178.27 (16)
C3—C4—C5—C6	−1.9 (3)	N1—C8—C9—C10	−179.91 (15)
C7—C4—C5—C6	173.05 (17)	C13—C8—C9—C10	1.9 (3)
C4—C5—C6—C1	−0.3 (3)	N2—C9—C10—C11	179.33 (17)
C4—C5—C6—Cl2	−178.32 (15)	C8—C9—C10—C11	−0.9 (3)
C2—C1—C6—C5	2.2 (3)	C9—C10—C11—C12	−0.6 (3)
Cl1—C1—C6—C5	−175.32 (15)	C9—C10—C11—C18	179.18 (16)
C2—C1—C6—Cl2	−179.79 (15)	C10—C11—C12—C13	1.2 (3)
Cl1—C1—C6—Cl2	2.6 (3)	C18—C11—C12—C13	−178.55 (17)
C9—N2—C7—N1	0.33 (19)	C11—C12—C13—C8	−0.3 (3)
C9—N2—C7—C4	−179.90 (15)	N1—C8—C13—C12	−178.92 (18)
C8—N1—C7—N2	−0.40 (19)	C9—C8—C13—C12	−1.3 (3)
C14—N1—C7—N2	178.24 (16)	C7—N1—C14—C15	102.0 (2)
C8—N1—C7—C4	179.85 (16)	C8—N1—C14—C15	−79.6 (2)
C14—N1—C7—C4	−1.5 (3)	N1—C14—C15—C16	−178.79 (16)
C5—C4—C7—N2	−33.9 (2)	C14—C15—C16—C17	−179.5 (2)
C3—C4—C7—N2	140.60 (18)	C19—O2—C18—O1	−0.3 (3)
C5—C4—C7—N1	145.81 (17)	C19—O2—C18—C11	178.78 (17)
C3—C4—C7—N1	−39.7 (3)	C10—C11—C18—O1	2.9 (3)
C7—N1—C8—C13	178.21 (18)	C12—C11—C18—O1	−177.28 (18)
C14—N1—C8—C13	−0.5 (3)	C10—C11—C18—O2	−176.11 (16)
C7—N1—C8—C9	0.29 (17)	C12—C11—C18—O2	3.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	0.93	2.53	3.336 (3)	146
C13—H13···O1^ii	0.93	2.41	3.340 (2)	176

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2.