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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804019610/su6109sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804019610/su6109Isup2.hkl
Contains datablock I

CCDC reference: 251722

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

Computing details top

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 top
Crystal data top
C19H18Cl2N2O2F(000) = 784
Mr = 377.25Dx = 1.364 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: - P 2ynCell parameters from 15013 reflections
a = 9.3359 (6) Åθ = 1.5–29.0°
b = 14.4051 (8) ŵ = 0.37 mm1
c = 16.3707 (11) ÅT = 293 K
β = 123.459 (4)°Prismatic, colourless
V = 1836.8 (2) Å30.50 × 0.30 × 0.10 mm
Z = 4
Data collection top
Stoe 2-circle goniometer
diffractometer
2727 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.088
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
Detector resolution: 6.67 pixels mm-1h = 1212
rotation method scansk = 1818
30007 measured reflectionsl = 2121
4133 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.0182P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
4133 reflectionsΔρmax = 0.29 e Å3
227 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0164 (18)
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cl11.28712 (9)0.80832 (4)0.66360 (6)0.0989 (3)
Cl21.20564 (9)0.72642 (5)0.81258 (5)0.0954 (3)
N20.85449 (18)0.42999 (10)0.62623 (10)0.0492 (3)
N10.65298 (17)0.46732 (9)0.46999 (10)0.0465 (3)
O10.67609 (19)0.11285 (10)0.69764 (10)0.0691 (4)
O20.44064 (18)0.08108 (9)0.55246 (10)0.0671 (4)
C11.1343 (3)0.72266 (13)0.62725 (17)0.0628 (5)
C21.0485 (3)0.68826 (13)0.53337 (17)0.0623 (5)
H21.06730.71430.48810.075*
C30.9346 (2)0.61533 (13)0.50577 (14)0.0547 (4)
H30.87700.59270.44200.066*
C40.9057 (2)0.57566 (12)0.57276 (13)0.0475 (4)
C50.9891 (2)0.61276 (13)0.66627 (14)0.0553 (4)
H50.96820.58800.71120.066*
C61.1019 (3)0.68550 (13)0.69378 (16)0.0624 (5)
C70.8044 (2)0.49135 (11)0.55597 (12)0.0460 (4)
C80.6044 (2)0.38289 (12)0.48794 (12)0.0457 (4)
C90.7311 (2)0.36112 (12)0.58523 (11)0.0451 (4)
C100.7202 (2)0.27947 (12)0.62645 (12)0.0484 (4)
H100.80440.26380.69080.058*
C110.5808 (2)0.22214 (12)0.56925 (12)0.0482 (4)
C120.4528 (2)0.24672 (13)0.47210 (13)0.0539 (4)
H120.35910.20750.43550.065*
C130.4623 (2)0.32675 (13)0.42992 (13)0.0530 (4)
H130.37780.34260.36570.064*
C140.5549 (2)0.51758 (13)0.37755 (13)0.0520 (4)
H14A0.58850.58240.38900.062*
H14B0.43380.51430.35310.062*
C150.5816 (3)0.47927 (14)0.30053 (13)0.0579 (5)
H15A0.70300.48130.32560.069*
H15B0.54570.41480.28810.069*
C160.4831 (3)0.53237 (17)0.20534 (15)0.0741 (6)
H16A0.51970.59670.21740.089*
H16B0.36170.53080.18030.089*
C170.5100 (5)0.4927 (2)0.12888 (19)0.1131 (10)
H17C0.44500.52820.06960.170*
H17B0.47220.42930.11590.170*
H17A0.62960.49550.15270.170*
C180.5735 (2)0.13495 (13)0.61444 (13)0.0511 (4)
C190.4281 (3)0.00616 (15)0.59155 (18)0.0766 (6)
H19A0.32880.03940.54160.115*
H19B0.41780.00540.64590.115*
H19C0.52920.04240.61320.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0903 (4)0.0663 (4)0.1471 (7)0.0239 (3)0.0699 (5)0.0026 (4)
Cl20.1080 (5)0.0814 (4)0.0769 (4)0.0321 (3)0.0384 (4)0.0254 (3)
N20.0494 (8)0.0505 (8)0.0434 (7)0.0028 (6)0.0228 (7)0.0021 (6)
N10.0474 (7)0.0488 (8)0.0411 (7)0.0038 (6)0.0230 (6)0.0044 (6)
O10.0735 (9)0.0667 (9)0.0523 (8)0.0140 (7)0.0253 (7)0.0074 (6)
O20.0740 (9)0.0629 (8)0.0553 (8)0.0225 (7)0.0299 (7)0.0030 (6)
C10.0610 (11)0.0469 (10)0.0867 (15)0.0009 (8)0.0445 (11)0.0064 (10)
C20.0681 (11)0.0554 (11)0.0793 (14)0.0102 (9)0.0507 (11)0.0187 (10)
C30.0559 (10)0.0566 (11)0.0549 (10)0.0060 (8)0.0326 (9)0.0073 (8)
C40.0469 (9)0.0477 (9)0.0498 (9)0.0029 (7)0.0278 (8)0.0026 (7)
C50.0610 (11)0.0530 (10)0.0550 (10)0.0037 (8)0.0339 (9)0.0003 (8)
C60.0613 (11)0.0529 (11)0.0672 (12)0.0042 (9)0.0318 (10)0.0043 (9)
C70.0458 (9)0.0483 (9)0.0436 (9)0.0018 (7)0.0246 (8)0.0003 (7)
C80.0459 (8)0.0482 (9)0.0424 (8)0.0029 (7)0.0241 (7)0.0014 (7)
C90.0436 (8)0.0489 (9)0.0395 (8)0.0007 (7)0.0209 (7)0.0005 (7)
C100.0488 (9)0.0514 (10)0.0410 (8)0.0012 (7)0.0222 (8)0.0013 (7)
C110.0489 (9)0.0504 (10)0.0442 (9)0.0012 (7)0.0250 (8)0.0008 (7)
C120.0502 (9)0.0570 (10)0.0488 (9)0.0078 (8)0.0238 (8)0.0052 (8)
C130.0464 (9)0.0597 (11)0.0409 (9)0.0004 (8)0.0165 (7)0.0013 (8)
C140.0490 (9)0.0559 (10)0.0467 (9)0.0087 (8)0.0236 (8)0.0094 (8)
C150.0553 (10)0.0690 (12)0.0446 (9)0.0024 (9)0.0246 (8)0.0033 (8)
C160.0737 (14)0.0888 (16)0.0514 (11)0.0068 (11)0.0292 (11)0.0134 (10)
C170.121 (2)0.164 (3)0.0573 (15)0.016 (2)0.0506 (16)0.0007 (16)
C180.0548 (10)0.0541 (10)0.0479 (10)0.0064 (8)0.0306 (9)0.0037 (8)
C190.0963 (17)0.0620 (13)0.0733 (14)0.0272 (11)0.0480 (13)0.0057 (10)
Geometric parameters (Å, º) top
Cl1—C11.725 (2)C10—C111.381 (2)
Cl2—C61.729 (2)C10—H100.9300
N2—C71.315 (2)C11—C121.410 (2)
N2—C91.382 (2)C11—C181.478 (3)
N1—C71.380 (2)C12—C131.372 (3)
N1—C81.385 (2)C12—H120.9300
N1—C141.458 (2)C13—H130.9300
O1—C181.198 (2)C14—C151.518 (3)
O2—C181.335 (2)C14—H14A0.9700
O2—C191.444 (2)C14—H14B0.9700
C1—C21.375 (3)C15—C161.510 (3)
C1—C61.389 (3)C15—H15A0.9700
C2—C31.382 (3)C15—H15B0.9700
C2—H20.9300C16—C171.517 (4)
C3—C41.388 (2)C16—H16A0.9700
C3—H30.9300C16—H16B0.9700
C4—C51.386 (2)C17—H17C0.9600
C4—C71.469 (2)C17—H17B0.9600
C5—C61.374 (3)C17—H17A0.9600
C5—H50.9300C19—H19A0.9600
C8—C131.388 (2)C19—H19B0.9600
C8—C91.399 (2)C19—H19C0.9600
C9—C101.387 (2)
C7—N2—C9104.98 (14)C13—C12—H12119.0
C7—N1—C8105.96 (13)C11—C12—H12119.0
C7—N1—C14129.65 (15)C12—C13—C8116.62 (16)
C8—N1—C14124.38 (14)C12—C13—H13121.7
C18—O2—C19115.94 (16)C8—C13—H13121.7
C2—C1—C6119.53 (18)N1—C14—C15112.65 (15)
C2—C1—Cl1120.31 (17)N1—C14—H14A109.1
C6—C1—Cl1120.11 (18)C15—C14—H14A109.1
C1—C2—C3120.56 (18)N1—C14—H14B109.1
C1—C2—H2119.7C15—C14—H14B109.1
C3—C2—H2119.7H14A—C14—H14B107.8
C2—C3—C4120.27 (19)C16—C15—C14112.83 (17)
C2—C3—H3119.9C16—C15—H15A109.0
C4—C3—H3119.9C14—C15—H15A109.0
C5—C4—C3118.60 (17)C16—C15—H15B109.0
C5—C4—C7115.90 (15)C14—C15—H15B109.0
C3—C4—C7125.28 (16)H15A—C15—H15B107.8
C6—C5—C4121.21 (18)C15—C16—C17112.2 (2)
C6—C5—H5119.4C15—C16—H16A109.2
C4—C5—H5119.4C17—C16—H16A109.2
C5—C6—C1119.8 (2)C15—C16—H16B109.2
C5—C6—Cl2118.79 (17)C17—C16—H16B109.2
C1—C6—Cl2121.42 (16)H16A—C16—H16B107.9
N2—C7—N1113.18 (15)C16—C17—H17C109.5
N2—C7—C4120.67 (15)C16—C17—H17B109.5
N1—C7—C4126.15 (15)H17C—C17—H17B109.5
N1—C8—C13131.88 (15)C16—C17—H17A109.5
N1—C8—C9105.58 (14)H17C—C17—H17A109.5
C13—C8—C9122.50 (16)H17B—C17—H17A109.5
N2—C9—C10129.60 (15)O1—C18—O2122.35 (17)
N2—C9—C8110.30 (14)O1—C18—C11124.48 (16)
C10—C9—C8120.10 (15)O2—C18—C11113.17 (15)
C11—C10—C9118.11 (15)O2—C19—H19A109.5
C11—C10—H10120.9O2—C19—H19B109.5
C9—C10—H10120.9H19A—C19—H19B109.5
C10—C11—C12120.69 (16)O2—C19—H19C109.5
C10—C11—C18117.05 (15)H19A—C19—H19C109.5
C12—C11—C18122.25 (16)H19B—C19—H19C109.5
C13—C12—C11121.95 (16)
C6—C1—C2—C32.0 (3)C14—N1—C8—C9178.45 (15)
Cl1—C1—C2—C3175.56 (14)C7—N2—C9—C10179.65 (18)
C1—C2—C3—C40.2 (3)C7—N2—C9—C80.13 (19)
C2—C3—C4—C52.1 (3)N1—C8—C9—N20.10 (18)
C2—C3—C4—C7172.29 (17)C13—C8—C9—N2178.27 (16)
C3—C4—C5—C61.9 (3)N1—C8—C9—C10179.91 (15)
C7—C4—C5—C6173.05 (17)C13—C8—C9—C101.9 (3)
C4—C5—C6—C10.3 (3)N2—C9—C10—C11179.33 (17)
C4—C5—C6—Cl2178.32 (15)C8—C9—C10—C110.9 (3)
C2—C1—C6—C52.2 (3)C9—C10—C11—C120.6 (3)
Cl1—C1—C6—C5175.32 (15)C9—C10—C11—C18179.18 (16)
C2—C1—C6—Cl2179.79 (15)C10—C11—C12—C131.2 (3)
Cl1—C1—C6—Cl22.6 (3)C18—C11—C12—C13178.55 (17)
C9—N2—C7—N10.33 (19)C11—C12—C13—C80.3 (3)
C9—N2—C7—C4179.90 (15)N1—C8—C13—C12178.92 (18)
C8—N1—C7—N20.40 (19)C9—C8—C13—C121.3 (3)
C14—N1—C7—N2178.24 (16)C7—N1—C14—C15102.0 (2)
C8—N1—C7—C4179.85 (16)C8—N1—C14—C1579.6 (2)
C14—N1—C7—C41.5 (3)N1—C14—C15—C16178.79 (16)
C5—C4—C7—N233.9 (2)C14—C15—C16—C17179.5 (2)
C3—C4—C7—N2140.60 (18)C19—O2—C18—O10.3 (3)
C5—C4—C7—N1145.81 (17)C19—O2—C18—C11178.78 (17)
C3—C4—C7—N139.7 (3)C10—C11—C18—O12.9 (3)
C7—N1—C8—C13178.21 (18)C12—C11—C18—O1177.28 (18)
C14—N1—C8—C130.5 (3)C10—C11—C18—O2176.11 (16)
C7—N1—C8—C90.29 (17)C12—C11—C18—O23.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.932.533.336 (3)146
C13—H13···O1ii0.932.413.340 (2)176
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x1/2, y+1/2, z1/2.
 

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