organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890

1,3-Di­benzyl-5-chloro-1H-benzimidazol-2(3H)-one

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques Université Sidi Mohamed Ben Abdallah, Fés, Morocco, bService Commun Rayons-X FR2599, Université Paul Sabatier, Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 17 July 2011; accepted 19 July 2011; online 23 July 2011)

In both independent mol­ecules of the title compound, C21H17ClN2O, the aromatic rings of the benzyl substituents are located on opposite sides of the benzimidazole ring systems. In one mol­ecule, the rings are aligned at 77.0 (1) and 78.1 (1)° with respect to the fused-ring system, whereas in the other mol­ecule the rings are aligned at 76.0 (1) and 76.9 (1)°. There is an inter­molecular Cl⋯O contact of 3.086 (1) Å.

Related literature

For the structure of monobenzyl-benzimidazol-3-one, see: Ouzidan et al. (2011[Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.]).

[Scheme 1]

Experimental

Crystal data
  • C21H17ClN2O

  • Mr = 348.82

  • Monoclinic, P 21 /c

  • a = 11.0380 (4) Å

  • b = 9.2863 (3) Å

  • c = 33.2679 (13) Å

  • β = 92.297 (2)°

  • V = 3407.3 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 293 K

  • 0.08 × 0.04 × 0.03 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.981, Tmax = 0.993

  • 22403 measured reflections

  • 5950 independent reflections

  • 3942 reflections with I > 2σ(I)

  • Rint = 0.073

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.159

  • S = 1.03

  • 5950 reflections

  • 451 parameters

  • H-atom parameters constrained

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

A recent study reported the synthesis of monobenzyl-benzimidazol-3-one by the reaction of benzyl chloride on benzimidazol-3-one (Ouzidan et al., 2011). The use of double the molar quantity of benzyl choride on 5-chlorobenzimidazol-3-one yielded the expected title dibenzyl analog (Scheme I, Fig. 1). In both independent molecules, the aromatic rings of the benzyl substituent lie of opposite sides of the planar benzimidazole fused-ring. In one molecule, the rings are aligned at 77.0 (1)° and 78.1 (1)° with respect to the fused-ring whereas in the other, the rings are aligned at 76.0 (1)° and 76.9 (1)°.

Related literature top

For the crystal structure of monobenzyl-benzimidazol-3-one, see: Ouzidan et al. (2011).

Experimental top

To 5-chloro-1H-benzimidazol-2(3H)-one (0.2 g, 1.18 mmol), potassium carbonate (0.40 g, 2.80 mmol), and tetra-n-butylammonium bromide (0.08 g, 0.23 mmol) in DMF (15 ml) was added benzyl chloride (0.33 g, 2.6 mmol). Stirring was continued at room temperature for 6 h. The salts were removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. The compound was recrystallized from hexane.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

Omitted from the refinement were (-1 0 2), (1 0 2), (0 1 2), (0 0 2), (0 1 1) and (-1 1 2) owing to bad agreement between observed and calculated structure factors.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two molecules of C21H17ClN2O at the 70% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.
1,3-Dibenzyl-5-chloro-1H-benzimidazol-2(3H)-one top
Crystal data top
C21H17ClN2OF(000) = 1456
Mr = 348.82Dx = 1.360 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2455 reflections
a = 11.0380 (4) Åθ = 2.5–24.4°
b = 9.2863 (3) ŵ = 0.24 mm1
c = 33.2679 (13) ÅT = 293 K
β = 92.297 (2)°Prism, colorless
V = 3407.3 (2) Å30.08 × 0.04 × 0.03 mm
Z = 8
Data collection top
Bruker X8 APEXII
diffractometer
5950 independent reflections
Radiation source: fine-focus sealed tube3942 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.981, Tmax = 0.993k = 1110
22403 measured reflectionsl = 3939
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.071P)2 + 2.3735P]
where P = (Fo2 + 2Fc2)/3
5950 reflections(Δ/σ)max = 0.001
451 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C21H17ClN2OV = 3407.3 (2) Å3
Mr = 348.82Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.0380 (4) ŵ = 0.24 mm1
b = 9.2863 (3) ÅT = 293 K
c = 33.2679 (13) Å0.08 × 0.04 × 0.03 mm
β = 92.297 (2)°
Data collection top
Bruker X8 APEXII
diffractometer
5950 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3942 reflections with I > 2σ(I)
Tmin = 0.981, Tmax = 0.993Rint = 0.073
22403 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.03Δρmax = 0.77 e Å3
5950 reflectionsΔρmin = 0.36 e Å3
451 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.34242 (8)0.76198 (10)0.10621 (3)0.0370 (3)
Cl20.16981 (8)1.64706 (10)0.03835 (3)0.0392 (3)
O10.6486 (2)0.2235 (3)0.23982 (7)0.0360 (6)
O20.1395 (2)0.9431 (3)0.06445 (8)0.0391 (7)
N10.5083 (2)0.3850 (3)0.21135 (8)0.0290 (7)
N20.6912 (2)0.3771 (3)0.18714 (9)0.0286 (7)
N30.0049 (2)1.1228 (3)0.05254 (9)0.0287 (7)
N40.1826 (2)1.1884 (3)0.06987 (9)0.0299 (7)
C10.5083 (3)0.4824 (4)0.17969 (10)0.0277 (8)
C20.4193 (3)0.5703 (4)0.16282 (10)0.0297 (8)
H20.34150.57300.17250.036*
C30.4529 (3)0.6548 (4)0.13040 (10)0.0282 (8)
C40.5684 (3)0.6555 (4)0.11589 (11)0.0332 (9)
H40.58680.71600.09470.040*
C50.6573 (3)0.5652 (4)0.13307 (11)0.0324 (9)
H50.73530.56360.12350.039*
C60.6258 (3)0.4786 (4)0.16458 (10)0.0256 (8)
C70.6200 (3)0.3167 (4)0.21566 (10)0.0288 (8)
C80.4026 (3)0.3441 (4)0.23430 (10)0.0325 (9)
H8A0.35340.42870.23870.039*
H8B0.43000.30700.26040.039*
C90.3263 (3)0.2313 (4)0.21252 (10)0.0264 (8)
C100.2142 (3)0.2636 (4)0.19518 (11)0.0320 (9)
H100.18240.35570.19770.038*
C110.1489 (3)0.1595 (4)0.17398 (11)0.0350 (9)
H110.07360.18250.16220.042*
C120.1940 (3)0.0227 (4)0.17016 (11)0.0364 (9)
H120.15010.04650.15560.044*
C130.3058 (3)0.0117 (4)0.18826 (11)0.0355 (9)
H130.33640.10470.18630.043*
C140.3710 (3)0.0919 (4)0.20903 (10)0.0326 (9)
H140.44610.06870.22100.039*
C150.8138 (3)0.3320 (4)0.17933 (11)0.0316 (9)
H15A0.81740.30310.15140.038*
H15B0.83420.24870.19590.038*
C160.9066 (3)0.4487 (4)0.18787 (10)0.0254 (8)
C170.9235 (3)0.5040 (5)0.22652 (11)0.0429 (10)
H170.87610.47070.24710.051*
C181.0100 (4)0.6077 (5)0.23439 (13)0.0555 (13)
H181.02110.64360.26040.067*
C191.0807 (3)0.6594 (4)0.20421 (12)0.0419 (10)
H191.13930.72920.20980.050*
C201.0637 (3)0.6071 (4)0.16622 (11)0.0359 (9)
H201.11040.64200.14570.043*
C210.9772 (3)0.5022 (4)0.15803 (11)0.0320 (9)
H210.96640.46710.13190.038*
C220.0032 (3)1.2731 (4)0.05389 (10)0.0252 (8)
C230.0928 (3)1.3738 (4)0.04580 (10)0.0285 (8)
H230.17211.34680.03900.034*
C240.0587 (3)1.5167 (4)0.04828 (10)0.0269 (8)
C250.0588 (3)1.5596 (4)0.05836 (10)0.0307 (8)
H250.07841.65700.05950.037*
C260.1466 (3)1.4569 (4)0.06670 (10)0.0301 (8)
H260.22571.48410.07380.036*
C270.1156 (3)1.3146 (4)0.06442 (10)0.0268 (8)
C280.1094 (3)1.0696 (4)0.06260 (10)0.0299 (8)
C290.1116 (3)1.0311 (4)0.04639 (10)0.0301 (8)
H29A0.08630.93730.03700.036*
H29B0.16491.07300.02570.036*
C300.1805 (3)1.0127 (4)0.08438 (10)0.0280 (8)
C310.1280 (3)0.9383 (4)0.11718 (12)0.0390 (10)
H310.05110.89890.11520.047*
C320.1877 (4)0.9221 (4)0.15238 (12)0.0450 (10)
H320.15130.87230.17390.054*
C330.3026 (4)0.9806 (5)0.15555 (13)0.0489 (11)
H330.34340.97060.17930.059*
C340.3563 (4)1.0533 (5)0.12353 (13)0.0475 (11)
H340.43361.09180.12560.057*
C350.2953 (3)1.0695 (4)0.08817 (12)0.0371 (9)
H350.33211.11920.06670.045*
C360.3085 (3)1.1791 (4)0.08465 (11)0.0316 (9)
H36A0.32621.08040.09240.038*
H36B0.31921.23860.10850.038*
C370.3976 (3)1.2263 (4)0.05408 (10)0.0275 (8)
C380.4760 (3)1.3383 (4)0.06241 (11)0.0314 (9)
H380.47221.38700.08680.038*
C390.5609 (3)1.3799 (4)0.03490 (12)0.0387 (10)
H390.61301.45660.04070.046*
C400.5674 (4)1.3065 (4)0.00092 (12)0.0411 (10)
H400.62471.33270.01930.049*
C410.4894 (4)1.1950 (5)0.00948 (12)0.0416 (10)
H410.49431.14580.03370.050*
C420.4036 (3)1.1548 (4)0.01745 (11)0.0352 (9)
H420.35001.08010.01110.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0347 (5)0.0362 (6)0.0402 (5)0.0082 (4)0.0016 (4)0.0039 (4)
Cl20.0399 (5)0.0284 (6)0.0497 (6)0.0047 (4)0.0066 (4)0.0039 (4)
O10.0320 (14)0.0387 (16)0.0369 (14)0.0017 (12)0.0031 (11)0.0085 (12)
O20.0315 (14)0.0280 (16)0.0577 (18)0.0055 (12)0.0008 (12)0.0016 (13)
N10.0250 (15)0.0309 (18)0.0312 (16)0.0041 (13)0.0011 (12)0.0009 (13)
N20.0198 (14)0.0301 (18)0.0356 (17)0.0008 (13)0.0011 (12)0.0049 (13)
N30.0226 (15)0.0261 (18)0.0374 (17)0.0011 (13)0.0002 (12)0.0005 (13)
N40.0205 (15)0.0319 (19)0.0373 (17)0.0009 (13)0.0014 (12)0.0021 (13)
C10.0258 (18)0.025 (2)0.0323 (19)0.0032 (16)0.0009 (15)0.0028 (16)
C20.0228 (18)0.030 (2)0.036 (2)0.0030 (16)0.0009 (15)0.0078 (17)
C30.0293 (19)0.019 (2)0.036 (2)0.0039 (15)0.0029 (15)0.0025 (16)
C40.034 (2)0.032 (2)0.034 (2)0.0004 (17)0.0013 (16)0.0058 (17)
C50.0253 (19)0.035 (2)0.037 (2)0.0041 (17)0.0012 (15)0.0005 (17)
C60.0199 (17)0.026 (2)0.0308 (19)0.0032 (15)0.0039 (14)0.0029 (15)
C70.028 (2)0.029 (2)0.0294 (19)0.0061 (16)0.0041 (15)0.0024 (17)
C80.032 (2)0.038 (2)0.0282 (19)0.0009 (17)0.0045 (15)0.0019 (17)
C90.0237 (18)0.028 (2)0.0284 (19)0.0016 (15)0.0091 (14)0.0002 (15)
C100.0276 (19)0.031 (2)0.038 (2)0.0022 (17)0.0055 (16)0.0024 (17)
C110.0220 (18)0.044 (3)0.039 (2)0.0030 (17)0.0007 (16)0.0032 (18)
C120.039 (2)0.035 (2)0.035 (2)0.0101 (18)0.0020 (17)0.0018 (17)
C130.045 (2)0.025 (2)0.037 (2)0.0007 (18)0.0072 (18)0.0018 (17)
C140.0296 (19)0.037 (2)0.031 (2)0.0005 (17)0.0014 (15)0.0065 (17)
C150.0218 (18)0.033 (2)0.039 (2)0.0016 (16)0.0010 (15)0.0000 (17)
C160.0170 (16)0.029 (2)0.0297 (18)0.0004 (15)0.0006 (14)0.0001 (15)
C170.038 (2)0.060 (3)0.031 (2)0.021 (2)0.0109 (17)0.0048 (19)
C180.050 (3)0.077 (3)0.040 (2)0.029 (2)0.008 (2)0.024 (2)
C190.032 (2)0.042 (3)0.052 (3)0.0153 (19)0.0048 (18)0.008 (2)
C200.0266 (19)0.040 (2)0.042 (2)0.0051 (18)0.0062 (16)0.0070 (18)
C210.0224 (18)0.044 (2)0.0298 (19)0.0029 (17)0.0001 (15)0.0023 (17)
C220.0250 (18)0.025 (2)0.0261 (18)0.0022 (16)0.0072 (14)0.0016 (15)
C230.0221 (18)0.034 (2)0.0293 (19)0.0020 (16)0.0018 (14)0.0025 (16)
C240.0302 (19)0.028 (2)0.0230 (17)0.0006 (16)0.0089 (14)0.0019 (15)
C250.035 (2)0.027 (2)0.031 (2)0.0110 (17)0.0089 (16)0.0000 (16)
C260.0259 (18)0.033 (2)0.032 (2)0.0083 (17)0.0056 (15)0.0019 (16)
C270.0250 (18)0.028 (2)0.0274 (18)0.0008 (16)0.0063 (14)0.0004 (15)
C280.0233 (18)0.034 (2)0.033 (2)0.0017 (17)0.0062 (15)0.0008 (17)
C290.0276 (19)0.025 (2)0.037 (2)0.0024 (16)0.0019 (15)0.0032 (16)
C300.0288 (19)0.020 (2)0.035 (2)0.0052 (15)0.0018 (15)0.0013 (15)
C310.030 (2)0.041 (3)0.046 (2)0.0028 (18)0.0019 (17)0.0043 (19)
C320.051 (3)0.043 (3)0.040 (2)0.006 (2)0.0014 (19)0.0093 (19)
C330.055 (3)0.049 (3)0.044 (2)0.010 (2)0.014 (2)0.001 (2)
C340.034 (2)0.048 (3)0.061 (3)0.003 (2)0.014 (2)0.001 (2)
C350.030 (2)0.035 (2)0.047 (2)0.0013 (17)0.0017 (17)0.0068 (18)
C360.0208 (18)0.040 (2)0.034 (2)0.0010 (16)0.0002 (15)0.0036 (17)
C370.0177 (17)0.029 (2)0.036 (2)0.0032 (15)0.0010 (14)0.0019 (16)
C380.0260 (19)0.032 (2)0.037 (2)0.0043 (17)0.0013 (15)0.0012 (17)
C390.027 (2)0.028 (2)0.060 (3)0.0050 (17)0.0038 (18)0.0095 (19)
C400.038 (2)0.043 (3)0.044 (2)0.008 (2)0.0166 (18)0.013 (2)
C410.045 (2)0.046 (3)0.034 (2)0.010 (2)0.0107 (18)0.0003 (18)
C420.031 (2)0.031 (2)0.043 (2)0.0032 (17)0.0011 (17)0.0048 (18)
Geometric parameters (Å, º) top
Cl1—C31.745 (3)C17—H170.9300
Cl2—C241.745 (3)C18—C191.382 (6)
O1—C71.214 (4)C18—H180.9300
O2—C281.222 (4)C19—C201.360 (5)
N1—C71.389 (4)C19—H190.9300
N1—C11.389 (4)C20—C211.384 (5)
N1—C81.470 (4)C20—H200.9300
N2—C71.376 (4)C21—H210.9300
N2—C61.389 (4)C22—C231.380 (5)
N2—C151.450 (4)C22—C271.397 (5)
N3—C281.384 (4)C23—C241.380 (5)
N3—C221.396 (4)C23—H230.9300
N3—C291.461 (4)C24—C251.386 (5)
N4—C281.383 (5)C25—C261.380 (5)
N4—C271.393 (4)C25—H250.9300
N4—C361.459 (4)C26—C271.367 (5)
C1—C21.379 (5)C26—H260.9300
C1—C61.410 (5)C29—C301.511 (5)
C2—C31.396 (5)C29—H29A0.9700
C2—H20.9300C29—H29B0.9700
C3—C41.381 (5)C30—C351.383 (5)
C4—C51.396 (5)C30—C311.398 (5)
C4—H40.9300C31—C321.375 (5)
C5—C61.377 (5)C31—H310.9300
C5—H50.9300C32—C331.388 (6)
C8—C91.511 (5)C32—H320.9300
C8—H8A0.9700C33—C341.375 (6)
C8—H8B0.9700C33—H330.9300
C9—C101.377 (5)C34—C351.387 (5)
C9—C141.392 (5)C34—H340.9300
C10—C111.382 (5)C35—H350.9300
C10—H100.9300C36—C371.508 (5)
C11—C121.373 (5)C36—H36A0.9700
C11—H110.9300C36—H36B0.9700
C12—C131.388 (5)C37—C381.375 (5)
C12—H120.9300C37—C421.392 (5)
C13—C141.372 (5)C38—C391.391 (5)
C13—H130.9300C38—H380.9300
C14—H140.9300C39—C401.377 (6)
C15—C161.510 (5)C39—H390.9300
C15—H15A0.9700C40—C411.369 (6)
C15—H15B0.9700C40—H400.9300
C16—C211.379 (5)C41—C421.381 (5)
C16—C171.390 (5)C41—H410.9300
C17—C181.374 (5)C42—H420.9300
C7—N1—C1110.4 (3)C19—C20—C21120.2 (3)
C7—N1—C8123.3 (3)C19—C20—H20119.9
C1—N1—C8125.9 (3)C21—C20—H20119.9
C7—N2—C6110.5 (3)C16—C21—C20121.1 (3)
C7—N2—C15124.7 (3)C16—C21—H21119.4
C6—N2—C15124.6 (3)C20—C21—H21119.4
C28—N3—C22109.7 (3)C23—C22—N3131.5 (3)
C28—N3—C29123.2 (3)C23—C22—C27121.3 (3)
C22—N3—C29126.7 (3)N3—C22—C27107.2 (3)
C28—N4—C27110.2 (3)C22—C23—C24116.6 (3)
C28—N4—C36123.6 (3)C22—C23—H23121.7
C27—N4—C36126.0 (3)C24—C23—H23121.7
C2—C1—N1132.2 (3)C23—C24—C25122.8 (3)
C2—C1—C6121.3 (3)C23—C24—Cl2117.9 (3)
N1—C1—C6106.4 (3)C25—C24—Cl2119.3 (3)
C1—C2—C3116.1 (3)C26—C25—C24119.5 (3)
C1—C2—H2121.9C26—C25—H25120.2
C3—C2—H2121.9C24—C25—H25120.2
C4—C3—C2123.4 (3)C27—C26—C25119.0 (3)
C4—C3—Cl1118.3 (3)C27—C26—H26120.5
C2—C3—Cl1118.4 (3)C25—C26—H26120.5
C3—C4—C5119.9 (3)C26—C27—N4132.5 (3)
C3—C4—H4120.1C26—C27—C22120.7 (3)
C5—C4—H4120.1N4—C27—C22106.8 (3)
C6—C5—C4117.9 (3)O2—C28—N4127.1 (3)
C6—C5—H5121.1O2—C28—N3126.8 (3)
C4—C5—H5121.1N4—C28—N3106.1 (3)
C5—C6—N2131.8 (3)N3—C29—C30112.3 (3)
C5—C6—C1121.4 (3)N3—C29—H29A109.2
N2—C6—C1106.9 (3)C30—C29—H29A109.2
O1—C7—N2127.4 (3)N3—C29—H29B109.2
O1—C7—N1126.8 (3)C30—C29—H29B109.2
N2—C7—N1105.8 (3)H29A—C29—H29B107.9
N1—C8—C9111.6 (3)C35—C30—C31118.0 (3)
N1—C8—H8A109.3C35—C30—C29121.8 (3)
C9—C8—H8A109.3C31—C30—C29120.2 (3)
N1—C8—H8B109.3C32—C31—C30121.4 (4)
C9—C8—H8B109.3C32—C31—H31119.3
H8A—C8—H8B108.0C30—C31—H31119.3
C10—C9—C14118.9 (3)C31—C32—C33119.5 (4)
C10—C9—C8121.6 (3)C31—C32—H32120.2
C14—C9—C8119.5 (3)C33—C32—H32120.2
C9—C10—C11120.2 (3)C34—C33—C32120.0 (4)
C9—C10—H10119.9C34—C33—H33120.0
C11—C10—H10119.9C32—C33—H33120.0
C12—C11—C10120.7 (3)C33—C34—C35120.1 (4)
C12—C11—H11119.6C33—C34—H34119.9
C10—C11—H11119.6C35—C34—H34119.9
C11—C12—C13119.5 (4)C30—C35—C34120.9 (4)
C11—C12—H12120.3C30—C35—H35119.5
C13—C12—H12120.3C34—C35—H35119.5
C14—C13—C12119.7 (4)N4—C36—C37113.2 (3)
C14—C13—H13120.1N4—C36—H36A108.9
C12—C13—H13120.1C37—C36—H36A108.9
C13—C14—C9120.9 (3)N4—C36—H36B108.9
C13—C14—H14119.5C37—C36—H36B108.9
C9—C14—H14119.5H36A—C36—H36B107.8
N2—C15—C16112.9 (3)C38—C37—C42119.1 (3)
N2—C15—H15A109.0C38—C37—C36120.4 (3)
C16—C15—H15A109.0C42—C37—C36120.5 (3)
N2—C15—H15B109.0C37—C38—C39120.8 (3)
C16—C15—H15B109.0C37—C38—H38119.6
H15A—C15—H15B107.8C39—C38—H38119.6
C21—C16—C17118.3 (3)C40—C39—C38119.5 (4)
C21—C16—C15121.4 (3)C40—C39—H39120.3
C17—C16—C15120.2 (3)C38—C39—H39120.3
C18—C17—C16120.1 (3)C41—C40—C39120.0 (4)
C18—C17—H17120.0C41—C40—H40120.0
C16—C17—H17120.0C39—C40—H40120.0
C17—C18—C19120.9 (4)C40—C41—C42120.8 (4)
C17—C18—H18119.6C40—C41—H41119.6
C19—C18—H18119.6C42—C41—H41119.6
C20—C19—C18119.4 (4)C41—C42—C37119.8 (4)
C20—C19—H19120.3C41—C42—H42120.1
C18—C19—H19120.3C37—C42—H42120.1
C7—N1—C1—C2177.0 (4)C28—N3—C22—C23178.8 (3)
C8—N1—C1—C24.2 (6)C29—N3—C22—C238.1 (6)
C7—N1—C1—C62.1 (4)C28—N3—C22—C271.0 (4)
C8—N1—C1—C6174.9 (3)C29—N3—C22—C27174.0 (3)
N1—C1—C2—C3179.5 (3)N3—C22—C23—C24177.0 (3)
C6—C1—C2—C30.4 (5)C27—C22—C23—C240.6 (5)
C1—C2—C3—C41.4 (5)C22—C23—C24—C250.1 (5)
C1—C2—C3—Cl1177.0 (3)C22—C23—C24—Cl2179.8 (2)
C2—C3—C4—C52.0 (6)C23—C24—C25—C260.6 (5)
Cl1—C3—C4—C5176.5 (3)Cl2—C24—C25—C26179.2 (3)
C3—C4—C5—C60.6 (5)C24—C25—C26—C270.7 (5)
C4—C5—C6—N2178.6 (3)C25—C26—C27—N4178.0 (3)
C4—C5—C6—C11.2 (5)C25—C26—C27—C220.1 (5)
C7—N2—C6—C5179.6 (4)C28—N4—C27—C26177.6 (4)
C15—N2—C6—C54.8 (6)C36—N4—C27—C267.7 (6)
C7—N2—C6—C10.2 (4)C28—N4—C27—C220.7 (4)
C15—N2—C6—C1175.0 (3)C36—N4—C27—C22174.0 (3)
C2—C1—C6—C51.7 (5)C23—C22—C27—C260.5 (5)
N1—C1—C6—C5179.0 (3)N3—C22—C27—C26177.6 (3)
C2—C1—C6—N2178.1 (3)C23—C22—C27—N4179.1 (3)
N1—C1—C6—N21.2 (4)N3—C22—C27—N41.0 (4)
C6—N2—C7—O1178.9 (3)C27—N4—C28—O2179.6 (3)
C15—N2—C7—O14.0 (6)C36—N4—C28—O25.6 (6)
C6—N2—C7—N11.5 (4)C27—N4—C28—N30.1 (4)
C15—N2—C7—N1176.3 (3)C36—N4—C28—N3174.7 (3)
C1—N1—C7—O1178.1 (3)C22—N3—C28—O2179.8 (3)
C8—N1—C7—O15.1 (5)C29—N3—C28—O26.4 (5)
C1—N1—C7—N22.2 (4)C22—N3—C28—N40.5 (4)
C8—N1—C7—N2175.3 (3)C29—N3—C28—N4173.9 (3)
C7—N1—C8—C990.5 (4)C28—N3—C29—C3092.6 (4)
C1—N1—C8—C981.5 (4)C22—N3—C29—C3079.6 (4)
N1—C8—C9—C10108.5 (4)N3—C29—C30—C35112.5 (4)
N1—C8—C9—C1470.1 (4)N3—C29—C30—C3166.6 (4)
C14—C9—C10—C111.4 (5)C35—C30—C31—C320.3 (6)
C8—C9—C10—C11177.2 (3)C29—C30—C31—C32178.8 (3)
C9—C10—C11—C120.5 (5)C30—C31—C32—C330.1 (6)
C10—C11—C12—C130.8 (5)C31—C32—C33—C340.4 (6)
C11—C12—C13—C141.3 (5)C32—C33—C34—C350.6 (6)
C12—C13—C14—C90.5 (5)C31—C30—C35—C340.2 (5)
C10—C9—C14—C130.9 (5)C29—C30—C35—C34179.0 (3)
C8—C9—C14—C13177.8 (3)C33—C34—C35—C300.3 (6)
C7—N2—C15—C16116.9 (4)C28—N4—C36—C37112.1 (4)
C6—N2—C15—C1668.9 (4)C27—N4—C36—C3773.9 (4)
N2—C15—C16—C21118.9 (4)N4—C36—C37—C38120.9 (4)
N2—C15—C16—C1761.7 (4)N4—C36—C37—C4260.6 (4)
C21—C16—C17—C181.0 (6)C42—C37—C38—C390.4 (5)
C15—C16—C17—C18178.4 (4)C36—C37—C38—C39178.1 (3)
C16—C17—C18—C190.5 (7)C37—C38—C39—C400.8 (5)
C17—C18—C19—C200.3 (7)C38—C39—C40—C410.9 (6)
C18—C19—C20—C210.6 (6)C39—C40—C41—C420.1 (6)
C17—C16—C21—C200.7 (5)C40—C41—C42—C371.3 (6)
C15—C16—C21—C20178.7 (3)C38—C37—C42—C411.4 (5)
C19—C20—C21—C160.1 (6)C36—C37—C42—C41177.0 (3)

Experimental details

Crystal data
Chemical formulaC21H17ClN2O
Mr348.82
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.0380 (4), 9.2863 (3), 33.2679 (13)
β (°) 92.297 (2)
V3)3407.3 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.08 × 0.04 × 0.03
Data collection
DiffractometerBruker X8 APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.981, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
22403, 5950, 3942
Rint0.073
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.159, 1.03
No. of reflections5950
No. of parameters451
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.77, 0.36

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

We thank Université Sidi Mohamed Ben Abdallah, Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationOuzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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