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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2767
https://doi.org/10.1107/S1600536811038840

N-(2-Chloro­phen­yl)-4-methyl­benzamide

Vinola Z. Rodrigues,a Peter Herich,b B. Thimme Gowdaa* and Jozef Kožíšekb

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
*Correspondence e-mail: gowdabt@yahoo.com

(Received 20 September 2011; accepted 21 September 2011; online 30 September 2011)

The asymmetric unit of the title compound, C14H12ClNO, contains two independent mol­ecules in which the dihedral angles between the two aromatic rings are 51.76 (6) and 51.48 (7)°. The crystal structure is stabilized by inter­molecular N—H⋯O hydrogen bonds, which link the mol­ecules into chains running along the c axis.

Related literature

For preparation of the title compound, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.]). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004[Arjunan, V., Mohan, S., Subramanian, S. & Gowda, B. T. (2004). Spectrochim. Acta Part A, 60, 1141-1159.]); Bowes et al. (2003[Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.]); Gowda et al. (2001[Gowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch.Teil A, 56, 386-394.]); Rodrigues et al. (2011[Rodrigues, V. Z., Fronc, M., Gowda, B. T. & Kožíšek, J. (2011). Acta Cryst. E67, o1500.]); Saeed et al. (2010[Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808-o2809.]) on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.]) and on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2005[Gowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch.Teil A, 60, 106-112.]).

[Scheme 1]

Experimental

Crystal data

  • C14H12ClNO

  • Mr = 245.70

  • Monoclinic, P 21 /n

  • a = 9.6940 (5) Å

  • b = 27.4495 (9) Å

  • c = 9.9025 (4) Å

  • β = 106.730 (5)°

  • V = 2523.48 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.29 mm−1

  • T = 293 K

  • 0.97 × 0.13 × 0.10 mm
Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) based on expressions derived by Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.957, Tmax = 0.972

  • 47577 measured reflections

  • 7045 independent reflections

  • 2850 reflections with I > 2σ(I)

  • Rint = 0.046
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.126

  • S = 0.85

  • 7045 reflections

  • 307 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N15—H15A⋯O34 0.86 2.02 2.8408 (16) 159
N32—H32A⋯O17i 0.86 2.01 2.8455 (16) 165
Symmetry code: (i) x, y, z-1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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: DIAMOND (Brandenburg, 2002[Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811038840/bt5650sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038840/bt5650Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811038840/bt5650Isup3.cml

checkCIF report


Comment top

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our work on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004; Bowes et al., 2003; Gowda et al., 2001; Saeed et al., 2010; Rodrigues et al., 2011), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda et al., 2005), in the present work, the crystal structure of N-(2-Chlorophenyl)-4-methylbenzamide (I) has been determined (Fig.1). The asymmetric unit of (I) contains two independent molecules. In the crystal, the ortho-Cl substituent in the anilino ring is positioned syn to the N–H bond in one of the molecules and anti in the other molecule. Further, the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other in both the molecules, similar to that observed in N-(2-methylphenyl)- 4-methylbenzamide (II)(Rodrigues et al., 2011).

The packing of molecules linked by N—H···O hydrogen bonds into infinite chains is shown in Fig. 2.

Related literature top

For preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004); Bowes et al. (2003); Gowda et al. (2001); Rodrigues et al. (2011); Saeed et al. (2010) on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005).

Experimental top

The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. cuboid-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Refinement top

All H atoms were visible in difference maps and then treated as riding atoms with C–H distances of 0.93Å (C-aromatic), 0.96Å (C-methyl) and N—H = 0.86 Å. The Uiso(H) values were set at 1.2 Ueq(C-aromatic, N) and 1.5 Ueq(C-methyl).

Structure description top

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our work on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004; Bowes et al., 2003; Gowda et al., 2001; Saeed et al., 2010; Rodrigues et al., 2011), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda et al., 2005), in the present work, the crystal structure of N-(2-Chlorophenyl)-4-methylbenzamide (I) has been determined (Fig.1). The asymmetric unit of (I) contains two independent molecules. In the crystal, the ortho-Cl substituent in the anilino ring is positioned syn to the N–H bond in one of the molecules and anti in the other molecule. Further, the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other in both the molecules, similar to that observed in N-(2-methylphenyl)- 4-methylbenzamide (II)(Rodrigues et al., 2011).

The packing of molecules linked by N—H···O hydrogen bonds into infinite chains is shown in Fig. 2.

For preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004); Bowes et al. (2003); Gowda et al. (2001); Rodrigues et al. (2011); Saeed et al. (2010) on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound. Molecular chains are generated by N—H···O hydrogen bonds which are shown by dashed lines. H atoms not involved in intermolecular bonding have been omitted.
N-(2-Chlorophenyl)-4-methylbenzamide top
Crystal data top
C14H12ClNOF(000) = 1024
Mr = 245.70Dx = 1.293 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 13361 reflections
a = 9.6940 (5) Åθ = 3.6–29.4°
b = 27.4495 (9) ŵ = 0.29 mm−1
c = 9.9025 (4) ÅT = 293 K
β = 106.730 (5)°Cuboid, colorless
V = 2523.48 (19) Å30.97 × 0.13 × 0.10 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		7045 independent reflections
Radiation source: fine-focus sealed tube2850 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 10.4340 pixels mm-1θmax = 29.4°, θmin = 3.6°
ω scansh = −13→13
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2009) based on expressions derived by Clark & Reid (1995)]		k = −37→37
Tmin = 0.957, Tmax = 0.972l = −13→12
47577 measured reflections
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 0.85 w = 1/[σ2(Fo2) + (0.0704P)2]
where P = (Fo2 + 2Fc2)/3
7045 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C14H12ClNOV = 2523.48 (19) Å3
Mr = 245.70Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.6940 (5) ŵ = 0.29 mm−1
b = 27.4495 (9) ÅT = 293 K
c = 9.9025 (4) Å0.97 × 0.13 × 0.10 mm
β = 106.730 (5)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		7045 independent reflections
Absorption correction: analytical
[CrysAlis RED (Oxford Diffraction, 2009) based on expressions derived by Clark & Reid (1995)]		2850 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.972Rint = 0.046
47577 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 0.85Δρmax = 0.24 e Å−3
7045 reflectionsΔρmin = −0.30 e Å−3
307 parameters
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
C10.4465 (2)0.18661 (6)0.78372 (15)0.0492 (4)
C20.5890 (2)0.19536 (7)0.85616 (18)0.0567 (5)
C30.6412 (3)0.24255 (8)0.8811 (2)0.0712 (6)
H3A0.73740.24810.92960.085*
C40.5494 (3)0.28101 (8)0.8336 (2)0.0794 (7)
H4A0.58390.31280.84950.095*
C50.4082 (3)0.27296 (8)0.7632 (2)0.0827 (7)
H5A0.34630.29910.73200.099*
C60.3572 (2)0.22594 (7)0.7386 (2)0.0676 (5)
H6A0.26080.22070.69060.081*
C70.3647 (2)0.10713 (6)0.83990 (16)0.0497 (4)
C80.30994 (18)0.05833 (6)0.78704 (16)0.0466 (4)
C90.2405 (2)0.04866 (7)0.64638 (17)0.0555 (5)
H9A0.22490.07380.58080.067*
C100.1947 (2)0.00242 (7)0.6028 (2)0.0653 (5)
H10A0.1467−0.00310.50830.078*
C110.2182 (2)−0.03609 (7)0.6964 (2)0.0677 (5)
C120.2852 (2)−0.02635 (7)0.8368 (2)0.0693 (6)
H12A0.3009−0.05160.90210.083*
C130.3290 (2)0.02018 (7)0.88200 (18)0.0583 (5)
H13A0.37190.02600.97740.070*
C140.1746 (4)−0.08743 (8)0.6468 (3)0.1105 (10)
H14C0.1994−0.10920.72600.133*
H14B0.2242−0.09710.58000.133*
H14A0.0725−0.08860.60280.133*
C180.3176 (2)0.05619 (6)0.25095 (15)0.0472 (4)
C190.1723 (2)0.04811 (6)0.18847 (17)0.0556 (5)
C200.1129 (2)0.00237 (8)0.1859 (2)0.0703 (6)
H20A0.0150−0.00250.14350.084*
C210.1995 (3)−0.03562 (8)0.2465 (2)0.0755 (6)
H21A0.1605−0.06670.24370.091*
C220.3426 (3)−0.02856 (7)0.3110 (2)0.0755 (6)
H22A0.4003−0.05460.35350.091*
C230.4020 (2)0.01741 (7)0.31306 (19)0.0624 (5)
H23A0.49970.02210.35680.075*
C240.41322 (19)0.13420 (6)0.35262 (16)0.0511 (4)
C250.44828 (19)0.18501 (6)0.32278 (15)0.0476 (4)
C260.4024 (2)0.20526 (6)0.18911 (17)0.0621 (5)
H26A0.35560.18580.11290.074*
C270.4250 (2)0.25370 (7)0.1674 (2)0.0683 (6)
H27A0.39300.26630.07650.082*
C280.4937 (2)0.28404 (7)0.2766 (2)0.0618 (5)
C290.5419 (2)0.26368 (7)0.4093 (2)0.0707 (6)
H29A0.59070.28320.48480.085*
C300.5195 (2)0.21513 (7)0.43291 (18)0.0606 (5)
H30A0.55260.20250.52370.073*
C310.5128 (3)0.33727 (7)0.2505 (3)0.0915 (7)
H31C0.56250.35290.33770.110*
H31B0.42020.35220.21240.110*
H31A0.56810.34070.18470.110*
N150.39382 (16)0.13853 (5)0.74748 (13)0.0507 (4)
H15A0.37990.12900.66180.061*
N320.37672 (17)0.10304 (5)0.24535 (13)0.0534 (4)
H32A0.39000.11200.16680.064*
O170.38313 (17)0.11887 (5)0.96324 (11)0.0771 (5)
O340.4147 (2)0.12111 (5)0.47127 (12)0.0924 (5)
Cl160.70621 (7)0.14715 (2)0.91490 (7)0.0936 (2)
Cl330.06234 (7)0.09610 (2)0.10827 (7)0.0956 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0709 (13)0.0453 (10)0.0353 (8)−0.0042 (9)0.0213 (8)0.0003 (7)
C20.0676 (14)0.0507 (11)0.0551 (10)−0.0015 (10)0.0228 (9)−0.0006 (8)
C30.0802 (15)0.0639 (14)0.0698 (13)−0.0166 (12)0.0220 (11)−0.0058 (10)
C40.114 (2)0.0492 (13)0.0813 (14)−0.0168 (14)0.0383 (15)−0.0030 (11)
C50.105 (2)0.0487 (13)0.0948 (16)0.0094 (13)0.0286 (15)0.0157 (11)
C60.0756 (14)0.0593 (13)0.0651 (12)0.0025 (11)0.0155 (10)0.0129 (10)
C70.0668 (12)0.0505 (10)0.0354 (9)−0.0018 (9)0.0203 (8)−0.0013 (7)
C80.0533 (11)0.0490 (10)0.0408 (9)−0.0024 (8)0.0187 (7)−0.0022 (8)
C90.0668 (12)0.0555 (11)0.0452 (9)−0.0073 (9)0.0175 (9)−0.0013 (8)
C100.0708 (14)0.0716 (14)0.0548 (11)−0.0152 (11)0.0202 (9)−0.0157 (10)
C110.0751 (14)0.0558 (12)0.0801 (14)−0.0189 (10)0.0351 (11)−0.0147 (11)
C120.0872 (16)0.0539 (12)0.0719 (13)−0.0079 (11)0.0309 (11)0.0086 (10)
C130.0735 (13)0.0547 (12)0.0478 (9)−0.0055 (10)0.0192 (9)0.0040 (9)
C140.145 (3)0.0753 (16)0.122 (2)−0.0446 (17)0.0568 (19)−0.0319 (15)
C180.0676 (13)0.0425 (10)0.0359 (8)−0.0033 (9)0.0218 (8)−0.0009 (7)
C190.0702 (14)0.0515 (11)0.0455 (9)−0.0003 (10)0.0172 (9)0.0017 (8)
C200.0780 (15)0.0693 (14)0.0619 (12)−0.0175 (12)0.0171 (10)−0.0064 (10)
C210.106 (2)0.0494 (12)0.0799 (14)−0.0162 (13)0.0409 (14)−0.0102 (11)
C220.103 (2)0.0470 (13)0.0871 (14)0.0161 (12)0.0443 (14)0.0128 (10)
C230.0660 (13)0.0630 (13)0.0610 (11)0.0055 (11)0.0228 (9)0.0065 (9)
C240.0676 (12)0.0538 (11)0.0357 (9)−0.0019 (9)0.0210 (8)−0.0024 (8)
C250.0581 (11)0.0484 (10)0.0398 (9)−0.0006 (8)0.0194 (8)−0.0032 (8)
C260.0951 (16)0.0470 (11)0.0432 (10)−0.0061 (10)0.0185 (9)−0.0058 (8)
C270.1027 (17)0.0506 (12)0.0544 (11)−0.0028 (11)0.0273 (11)0.0041 (9)
C280.0671 (13)0.0489 (11)0.0769 (13)−0.0062 (10)0.0326 (10)−0.0050 (10)
C290.0736 (15)0.0660 (13)0.0696 (13)−0.0172 (11)0.0159 (11)−0.0206 (11)
C300.0692 (13)0.0615 (12)0.0469 (10)−0.0078 (10)0.0100 (9)−0.0059 (9)
C310.109 (2)0.0522 (13)0.1262 (19)−0.0105 (13)0.0550 (16)−0.0083 (13)
N150.0737 (10)0.0472 (8)0.0339 (7)−0.0094 (7)0.0200 (7)−0.0038 (6)
N320.0805 (11)0.0490 (9)0.0340 (7)−0.0119 (7)0.0215 (7)−0.0006 (6)
O170.1376 (14)0.0618 (8)0.0409 (7)−0.0250 (8)0.0399 (7)−0.0084 (6)
O340.1802 (17)0.0653 (9)0.0414 (7)−0.0260 (10)0.0475 (9)−0.0063 (6)
Cl160.0746 (4)0.0705 (4)0.1285 (5)0.0101 (3)0.0178 (3)0.0039 (3)
Cl330.0833 (4)0.0885 (4)0.1050 (5)0.0137 (3)0.0112 (3)0.0323 (3)
Geometric parameters (Å, º) top
C1—C61.375 (3)C18—C191.384 (3)
C1—C21.382 (3)C18—N321.415 (2)
C1—N151.423 (2)C19—C201.379 (3)
C2—C31.387 (3)C19—Cl331.7365 (19)
C2—Cl161.732 (2)C20—C211.365 (3)
C3—C41.374 (3)C20—H20A0.9300
C3—H3A0.9300C21—C221.364 (3)
C4—C51.364 (3)C21—H21A0.9300
C4—H4A0.9300C22—C231.385 (3)
C5—C61.378 (3)C22—H22A0.9300
C5—H5A0.9300C23—H23A0.9300
C6—H6A0.9300C24—O341.2248 (17)
C7—O171.2255 (17)C24—N321.330 (2)
C7—N151.345 (2)C24—C251.485 (2)
C7—C81.480 (2)C25—C301.384 (2)
C8—C131.384 (2)C25—C261.386 (2)
C8—C91.387 (2)C26—C271.374 (3)
C9—C101.373 (3)C26—H26A0.9300
C9—H9A0.9300C27—C281.375 (3)
C10—C111.381 (3)C27—H27A0.9300
C10—H10A0.9300C28—C291.380 (3)
C11—C121.380 (3)C28—C311.505 (3)
C11—C141.512 (3)C29—C301.381 (3)
C12—C131.379 (3)C29—H29A0.9300
C12—H12A0.9300C30—H30A0.9300
C13—H13A0.9300C31—H31C0.9600
C14—H14C0.9600C31—H31B0.9600
C14—H14B0.9600C31—H31A0.9600
C14—H14A0.9600N15—H15A0.8600
C18—C231.375 (2)N32—H32A0.8600
C6—C1—C2118.26 (17)C20—C19—C18121.37 (18)
C6—C1—N15119.97 (17)C20—C19—Cl33118.95 (17)
C2—C1—N15121.63 (16)C18—C19—Cl33119.67 (14)
C1—C2—C3120.95 (18)C21—C20—C19119.1 (2)
C1—C2—Cl16120.17 (14)C21—C20—H20A120.4
C3—C2—Cl16118.88 (17)C19—C20—H20A120.4
C4—C3—C2119.3 (2)C22—C21—C20120.8 (2)
C4—C3—H3A120.3C22—C21—H21A119.6
C2—C3—H3A120.3C20—C21—H21A119.6
C5—C4—C3120.4 (2)C21—C22—C23119.9 (2)
C5—C4—H4A119.8C21—C22—H22A120.0
C3—C4—H4A119.8C23—C22—H22A120.0
C4—C5—C6119.9 (2)C18—C23—C22120.5 (2)
C4—C5—H5A120.1C18—C23—H23A119.8
C6—C5—H5A120.1C22—C23—H23A119.8
C1—C6—C5121.2 (2)O34—C24—N32120.29 (15)
C1—C6—H6A119.4O34—C24—C25121.75 (14)
C5—C6—H6A119.4N32—C24—C25117.94 (13)
O17—C7—N15120.71 (15)C30—C25—C26117.58 (16)
O17—C7—C8121.67 (14)C30—C25—C24119.67 (14)
N15—C7—C8117.62 (13)C26—C25—C24122.55 (15)
C13—C8—C9117.97 (16)C27—C26—C25121.04 (16)
C13—C8—C7118.71 (14)C27—C26—H26A119.5
C9—C8—C7123.32 (15)C25—C26—H26A119.5
C10—C9—C8120.80 (17)C26—C27—C28121.73 (17)
C10—C9—H9A119.6C26—C27—H27A119.1
C8—C9—H9A119.6C28—C27—H27A119.1
C9—C10—C11121.40 (17)C27—C28—C29117.26 (17)
C9—C10—H10A119.3C27—C28—C31120.59 (19)
C11—C10—H10A119.3C29—C28—C31122.15 (19)
C12—C11—C10117.82 (17)C28—C29—C30121.68 (17)
C12—C11—C14121.0 (2)C28—C29—H29A119.2
C10—C11—C14121.2 (2)C30—C29—H29A119.2
C13—C12—C11121.17 (17)C29—C30—C25120.69 (17)
C13—C12—H12A119.4C29—C30—H30A119.7
C11—C12—H12A119.4C25—C30—H30A119.7
C12—C13—C8120.78 (17)C28—C31—H31C109.5
C12—C13—H13A119.6C28—C31—H31B109.5
C8—C13—H13A119.6H31C—C31—H31B109.5
C11—C14—H14C109.5C28—C31—H31A109.5
C11—C14—H14B109.5H31C—C31—H31A109.5
H14C—C14—H14B109.5H31B—C31—H31A109.5
C11—C14—H14A109.5C7—N15—C1123.57 (12)
H14C—C14—H14A109.5C7—N15—H15A118.2
H14B—C14—H14A109.5C1—N15—H15A118.2
C23—C18—C19118.30 (16)C24—N32—C18124.80 (13)
C23—C18—N32121.70 (17)C24—N32—H32A117.6
C19—C18—N32119.96 (16)C18—N32—H32A117.6
C6—C1—C2—C3−0.8 (2)C18—C19—C20—C210.0 (3)
N15—C1—C2—C3174.95 (14)Cl33—C19—C20—C21178.76 (15)
C6—C1—C2—Cl16−179.78 (13)C19—C20—C21—C221.1 (3)
N15—C1—C2—Cl16−4.0 (2)C20—C21—C22—C23−1.3 (3)
C1—C2—C3—C40.3 (3)C19—C18—C23—C220.9 (2)
Cl16—C2—C3—C4179.27 (15)N32—C18—C23—C22−176.82 (15)
C2—C3—C4—C50.4 (3)C21—C22—C23—C180.3 (3)
C3—C4—C5—C6−0.5 (3)O34—C24—C25—C3017.0 (3)
C2—C1—C6—C50.7 (3)N32—C24—C25—C30−164.36 (17)
N15—C1—C6—C5−175.18 (16)O34—C24—C25—C26−157.66 (19)
C4—C5—C6—C10.0 (3)N32—C24—C25—C2621.0 (3)
O17—C7—C8—C13−23.7 (3)C30—C25—C26—C27−1.0 (3)
N15—C7—C8—C13156.29 (17)C24—C25—C26—C27173.79 (19)
O17—C7—C8—C9156.49 (18)C25—C26—C27—C280.0 (3)
N15—C7—C8—C9−23.5 (3)C26—C27—C28—C291.2 (3)
C13—C8—C9—C10−1.2 (3)C26—C27—C28—C31−178.1 (2)
C7—C8—C9—C10178.60 (17)C27—C28—C29—C30−1.5 (3)
C8—C9—C10—C11−1.2 (3)C31—C28—C29—C30177.8 (2)
C9—C10—C11—C122.3 (3)C28—C29—C30—C250.5 (3)
C9—C10—C11—C14−176.7 (2)C26—C25—C30—C290.7 (3)
C10—C11—C12—C13−0.9 (3)C24—C25—C30—C29−174.21 (18)
C14—C11—C12—C13178.0 (2)O17—C7—N15—C1−0.2 (3)
C11—C12—C13—C8−1.4 (3)C8—C7—N15—C1179.78 (16)
C9—C8—C13—C122.5 (3)C6—C1—N15—C7−107.11 (19)
C7—C8—C13—C12−177.30 (18)C2—C1—N15—C777.2 (2)
C23—C18—C19—C20−1.0 (2)O34—C24—N32—C189.7 (3)
N32—C18—C19—C20176.71 (15)C25—C24—N32—C18−168.96 (16)
C23—C18—C19—Cl33−179.72 (12)C23—C18—N32—C24−77.9 (2)
N32—C18—C19—Cl33−2.0 (2)C19—C18—N32—C24104.46 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N15—H15A···O340.862.022.8408 (16)159
N32—H32A···O17i0.862.012.8455 (16)165
Symmetry code: (i) x, y, z−1.

Experimental details

Crystal data
Chemical formulaC14H12ClNO
Mr245.70
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)9.6940 (5), 27.4495 (9), 9.9025 (4)
β (°) 106.730 (5)
V (Å3)2523.48 (19)
Z8
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.97 × 0.13 × 0.10
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
Absorption correctionAnalytical
[CrysAlis RED (Oxford Diffraction, 2009) based on expressions derived by Clark & Reid (1995)]
Tmin, Tmax0.957, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections		47577, 7045, 2850
Rint0.046
(sin θ/λ)max (Å−1)0.692
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.126, 0.85
No. of reflections7045
No. of parameters307
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.30

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N15—H15A···O340.862.022.8408 (16)158.7
N32—H32A···O17i0.862.012.8455 (16)164.8
Symmetry code: (i) x, y, z−1.
 

Acknowledgements

MF and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202–10) for their financial support and the Structural Funds, Inter­reg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for award of an RFSMS research fellowship.

References

First citationAllen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationArjunan, V., Mohan, S., Subramanian, S. & Gowda, B. T. (2004). Spectrochim. Acta Part A, 60, 1141–1159.  CrossRef CAS Google Scholar
 First citationBowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationBrandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationClark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230.  CAS Google Scholar
 First citationGowda, B. T., Paulus, H. & Fuess, H. (2001). Z. Naturforsch.Teil A, 56, 386–394.  CAS Google Scholar
 First citationGowda, B. T., Shetty, M. & Jayalakshmi, K. L. (2005). Z. Naturforsch.Teil A, 60, 106–112.  CAS Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationRodrigues, V. Z., Fronc, M., Gowda, B. T. & Kožíšek, J. (2011). Acta Cryst. E67, o1500.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSaeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808–o2809.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2767
https://doi.org/10.1107/S1600536811038840
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