4-Chloro-N-(3-methoxy­phen­yl)­benz­amide

Saeed, A.; Khera, R.A.; Abbas, N.; Simpson, J.; Stanley, R.G.

doi:10.1107/S1600536808029899

4-Chloro-N-(3-methoxyphenyl)benzamide

A. Saeed, R. A. Khera, N. Abbas, J. Simpson and R. G. Stanley

The title benzamide derivative, C₁₄H₁₂ClNO₂, crystallizes with two independent molecules in the asymmetric unit. Both are close to being planar, with dihedral angles between the two benzene rings of 11.92 (6) and 12.80 (7)°. In the crystal structure, N—H

O hydrogen bonds link molecules into chains along a. These interactions are augmented by C—H

O hydrogen bonds to form two-dimensional layers in the ac plane. Additional C—H

O interactions result in a three-dimensional network consisting of undulating rows along c. The crystal studied was an inversion twin with a 0.59 (3):0.41 (3) domain ratio.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808029899/hb2792sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808029899/hb2792Isup2.hkl Contains datablock I

CCDC reference: 706098

checkCIF report

Key indicators

Single-crystal X-ray study
T = 91 K
Mean (C-C) = 0.002 Å
R factor = 0.034
wR factor = 0.087
Data-to-parameter ratio = 26.8

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.590
           From the CIF: _refine_ls_abs_structure_Flack_su    0.030
PLAT033_ALERT_4_C Flack Parameter Value Deviates from Zero .......       0.59
PLAT063_ALERT_4_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels ..........          2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           33.45
           From the CIF: _reflns_number_total               8997
           Count of symmetry unique reflns         5416
           Completeness (_total/calc)            166.12%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3581
           Fraction of Friedel pairs measured     0.661
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Benzanilides have important uses in organic synthesis (e.g. Zhichkin et al., 2007) and show biological activity (e.g. Igawa et al., 1999).

The title compound, (I), crystallized as an inversion twin in the crystal studied with two independent molecules, A and B, in the asymmetric unit. Bond distances and angles within the molecules are normal (Allen et al., 1987). Each molecule deviates slightly from planarity with dihedral angles between the two benzene rings of 11.92 (6)° for A and 12.80 (7)° for B.

In the crystal structure, N—H···O hydrogen bonds link molecules into chains along a (Table 1). These interactions are augmented by C—H···O hydrogen bonds to form two dimensional layers in the ac plane, Fig 2. Additional C—H···O interactions result in a three dimensional network consisting of undulating rows along c, Fig 3.

Related literature top

For background on the applications of benzanilides, see: Zhichkin et al. (2007); Igawa et al. (1999). For reference structural data, see: Allen et al. (1987).

Experimental top

4-Chorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 3-methoxyaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 4 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aqueous 1 M HCl and saturated aqueous NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue from CHCl₃ afforded the title compound (yield = 81%) as colourless needles: Analysis calculated. for C₁₄H₁₂Cl_NO₂: C 64.25, H 4.62, N 5.35%; found: C 64.19, H 4.68, N 5.30%.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006) and SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
	Fig. 2. The two dimensional network in (I) formed by N—H···O and C—H···O interactions.
	Fig. 3. Crystal packing of (I) viewed down the a axis.

4-Chloro-N-(3-methoxyphenyl)benzamide top

Crystal data top

C₁₄H₁₂ClNO₂	F(000) = 1088
M_r = 261.70	D_x = 1.393 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8842 reflections
a = 9.6952 (4) Å	θ = 2.3–32.7°
b = 10.5671 (3) Å	µ = 0.30 mm⁻¹
c = 24.3512 (8) Å	T = 91 K
V = 2494.78 (15) Å³	Rod, colourless
Z = 8	0.80 × 0.27 × 0.18 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	8997 independent reflections
Radiation source: fine-focus sealed tube	8334 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 33.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −14→11
T_min = 0.771, T_max = 0.948	k = −16→16
47170 measured reflections	l = −35→36

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0497P)² + 0.3361P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
8997 reflections	Δρ_max = 0.43 e Å⁻³
336 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 3581 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.59 (3)

Crystal data top

C₁₄H₁₂ClNO₂	V = 2494.78 (15) Å³
M_r = 261.70	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.6952 (4) Å	µ = 0.30 mm⁻¹
b = 10.5671 (3) Å	T = 91 K
c = 24.3512 (8) Å	0.80 × 0.27 × 0.18 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	8997 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	8334 reflections with I > 2σ(I)
T_min = 0.771, T_max = 0.948	R_int = 0.038
47170 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	Δρ_max = 0.43 e Å⁻³
S = 1.05	Δρ_min = −0.26 e Å⁻³
8997 reflections	Absolute structure: Flack (1983), 3581 Friedel pairs
336 parameters	Absolute structure parameter: 0.59 (3)
0 restraints

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

	x	y	z	U_iso*/U_eq
C1A	0.44661 (12)	−0.01256 (11)	0.37778 (4)	0.01480 (19)
O1A	0.33061 (9)	−0.01825 (10)	0.39873 (4)	0.0241 (2)
C2A	0.46264 (12)	0.02718 (10)	0.31915 (4)	0.01340 (18)
C3A	0.36632 (12)	0.11223 (11)	0.29781 (5)	0.0164 (2)
H3A	0.2946	0.1434	0.3207	0.020*
C4A	0.37391 (13)	0.15185 (11)	0.24357 (5)	0.0172 (2)
H4A	0.3095	0.2113	0.2295	0.021*
C5A	0.47765 (13)	0.10288 (10)	0.21016 (4)	0.0166 (2)
Cl1A	0.48931 (4)	0.15338 (3)	0.142463 (11)	0.02479 (7)
C6A	0.57279 (13)	0.01592 (11)	0.22997 (4)	0.0175 (2)
H6A	0.6418	−0.0180	0.2065	0.021*
C7A	0.56516 (12)	−0.02073 (10)	0.28487 (4)	0.01525 (19)
H7A	0.6306	−0.0791	0.2991	0.018*
N1A	0.56370 (10)	−0.04026 (9)	0.40506 (4)	0.01410 (17)
H1NA	0.6396 (18)	−0.0282 (16)	0.3886 (7)	0.021 (4)*
C8A	0.57503 (12)	−0.08292 (10)	0.46008 (4)	0.01315 (18)
C9A	0.47507 (12)	−0.05885 (10)	0.49949 (4)	0.01510 (19)
H9A	0.3933	−0.0145	0.4899	0.018*
C10A	0.49561 (12)	−0.10044 (10)	0.55337 (4)	0.0160 (2)
O2A	0.39068 (10)	−0.07027 (9)	0.58869 (3)	0.02047 (17)
C14A	0.39789 (14)	−0.11940 (12)	0.64324 (5)	0.0224 (2)
H14A	0.3922	−0.2120	0.6421	0.034*
H14B	0.3210	−0.0859	0.6650	0.034*
H14C	0.4854	−0.0941	0.6601	0.034*
C11A	0.61594 (13)	−0.16314 (11)	0.56841 (5)	0.0179 (2)
H11A	0.6298	−0.1903	0.6052	0.021*
C12A	0.71576 (13)	−0.18529 (11)	0.52836 (5)	0.0185 (2)
H12A	0.7989	−0.2270	0.5383	0.022*
C13A	0.69619 (12)	−0.14772 (11)	0.47434 (5)	0.0162 (2)
H13A	0.7641	−0.1656	0.4473	0.019*
C1B	−0.05241 (12)	−0.00261 (10)	0.37999 (4)	0.01368 (19)
O1B	−0.16985 (9)	−0.00419 (9)	0.36016 (3)	0.01997 (17)
C2B	−0.02802 (12)	0.04716 (10)	0.43684 (4)	0.01360 (18)
C3B	0.07492 (12)	−0.00094 (11)	0.47086 (4)	0.01501 (19)
H3B	0.1339	−0.0660	0.4577	0.018*
C4B	0.09238 (13)	0.04536 (11)	0.52393 (4)	0.0172 (2)
H4B	0.1618	0.0118	0.5473	0.021*
C5B	0.00613 (13)	0.14154 (10)	0.54198 (4)	0.0171 (2)
Cl1B	0.02837 (4)	0.19996 (3)	0.608166 (12)	0.02653 (7)
C6B	−0.09805 (13)	0.19097 (11)	0.50899 (5)	0.0193 (2)
H6B	−0.1558	0.2570	0.5221	0.023*
C7B	−0.11618 (13)	0.14216 (11)	0.45660 (5)	0.0174 (2)
H7B	−0.1886	0.1732	0.4340	0.021*
N1B	0.06041 (10)	−0.04339 (9)	0.35250 (4)	0.01450 (17)
H1NB	0.1425 (18)	−0.0346 (16)	0.3682 (7)	0.021 (4)*
C8B	0.06282 (12)	−0.09968 (10)	0.29958 (4)	0.01377 (19)
C9B	−0.04236 (12)	−0.08284 (11)	0.26127 (4)	0.0157 (2)
H9B	−0.1206	−0.0327	0.2701	0.019*
C10B	−0.03149 (13)	−0.14050 (11)	0.20975 (4)	0.0163 (2)
O2B	−0.14035 (10)	−0.11702 (9)	0.17528 (4)	0.02185 (18)
C14B	−0.13097 (13)	−0.16277 (12)	0.12016 (4)	0.0205 (2)
H14D	−0.0436	−0.1350	0.1039	0.031*
H14E	−0.2080	−0.1292	0.0985	0.031*
H14F	−0.1349	−0.2554	0.1202	0.031*
C11B	0.08319 (13)	−0.21239 (11)	0.19574 (5)	0.0193 (2)
H11B	0.0899	−0.2509	0.1606	0.023*
C12B	0.18814 (14)	−0.22688 (12)	0.23434 (5)	0.0204 (2)
H12B	0.2675	−0.2751	0.2251	0.024*
C13B	0.17912 (13)	−0.17224 (11)	0.28614 (5)	0.0175 (2)
H13B	0.2510	−0.1839	0.3122	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0113 (5)	0.0201 (5)	0.0130 (4)	−0.0011 (4)	−0.0008 (4)	0.0000 (3)
O1A	0.0102 (4)	0.0468 (6)	0.0152 (4)	−0.0008 (4)	0.0008 (3)	0.0043 (4)
C2A	0.0114 (5)	0.0159 (4)	0.0129 (4)	−0.0015 (4)	−0.0004 (4)	−0.0008 (3)
C3A	0.0152 (5)	0.0199 (5)	0.0142 (4)	0.0028 (4)	−0.0003 (4)	−0.0018 (4)
C4A	0.0194 (5)	0.0167 (4)	0.0155 (4)	0.0020 (4)	−0.0035 (4)	−0.0001 (4)
C5A	0.0193 (5)	0.0188 (4)	0.0116 (4)	−0.0043 (4)	−0.0018 (4)	0.0007 (3)
Cl1A	0.03200 (17)	0.02910 (14)	0.01326 (10)	−0.00233 (12)	0.00006 (11)	0.00451 (9)
C6A	0.0160 (5)	0.0236 (5)	0.0129 (4)	0.0002 (4)	0.0015 (4)	−0.0023 (4)
C7A	0.0126 (5)	0.0188 (4)	0.0143 (4)	0.0016 (4)	−0.0010 (4)	−0.0014 (4)
N1A	0.0097 (4)	0.0202 (4)	0.0124 (4)	−0.0002 (3)	0.0005 (3)	0.0010 (3)
C8A	0.0125 (5)	0.0151 (4)	0.0118 (4)	−0.0022 (4)	−0.0016 (4)	0.0005 (3)
C9A	0.0130 (5)	0.0179 (4)	0.0144 (4)	0.0006 (4)	−0.0009 (4)	0.0008 (3)
C10A	0.0164 (5)	0.0173 (4)	0.0143 (4)	−0.0004 (4)	0.0004 (4)	0.0005 (3)
O2A	0.0190 (4)	0.0299 (4)	0.0125 (3)	0.0046 (4)	0.0033 (3)	0.0028 (3)
C14A	0.0258 (6)	0.0283 (6)	0.0129 (4)	−0.0009 (5)	0.0033 (5)	0.0034 (4)
C11A	0.0192 (5)	0.0199 (5)	0.0145 (4)	0.0013 (4)	−0.0012 (4)	0.0036 (4)
C12A	0.0170 (5)	0.0191 (5)	0.0194 (5)	0.0036 (4)	−0.0018 (4)	0.0036 (4)
C13A	0.0132 (5)	0.0182 (5)	0.0174 (5)	0.0012 (4)	0.0012 (4)	0.0019 (4)
C1B	0.0103 (5)	0.0179 (4)	0.0128 (4)	0.0003 (4)	0.0025 (3)	0.0020 (3)
O1B	0.0096 (4)	0.0351 (5)	0.0152 (3)	0.0004 (3)	0.0008 (3)	−0.0002 (3)
C2B	0.0115 (5)	0.0172 (4)	0.0121 (4)	−0.0004 (4)	0.0022 (4)	0.0015 (3)
C3B	0.0129 (5)	0.0187 (4)	0.0135 (4)	0.0023 (4)	0.0020 (4)	−0.0005 (4)
C4B	0.0157 (5)	0.0220 (5)	0.0138 (4)	0.0014 (4)	0.0010 (4)	−0.0009 (4)
C5B	0.0197 (6)	0.0184 (4)	0.0133 (4)	−0.0021 (4)	0.0040 (4)	−0.0032 (3)
Cl1B	0.03451 (17)	0.02830 (14)	0.01679 (11)	−0.00085 (13)	0.00243 (12)	−0.00894 (10)
C6B	0.0214 (6)	0.0177 (4)	0.0188 (5)	0.0048 (4)	0.0065 (4)	−0.0002 (4)
C7B	0.0160 (5)	0.0206 (5)	0.0157 (5)	0.0037 (4)	0.0030 (4)	0.0026 (4)
N1B	0.0094 (4)	0.0220 (4)	0.0121 (4)	0.0009 (3)	−0.0001 (3)	−0.0009 (3)
C8B	0.0129 (5)	0.0172 (4)	0.0113 (4)	−0.0006 (4)	0.0017 (4)	0.0005 (3)
C9B	0.0134 (5)	0.0201 (5)	0.0137 (4)	0.0022 (4)	0.0008 (4)	−0.0011 (4)
C10B	0.0158 (5)	0.0199 (5)	0.0133 (4)	0.0009 (4)	−0.0003 (4)	−0.0008 (3)
O2B	0.0181 (4)	0.0333 (5)	0.0142 (3)	0.0051 (4)	−0.0031 (3)	−0.0068 (3)
C14B	0.0219 (6)	0.0268 (5)	0.0127 (4)	−0.0008 (5)	0.0004 (4)	−0.0045 (4)
C11B	0.0203 (6)	0.0210 (5)	0.0165 (5)	0.0044 (4)	0.0011 (4)	−0.0033 (4)
C12B	0.0182 (6)	0.0234 (5)	0.0195 (5)	0.0075 (5)	0.0008 (4)	−0.0022 (4)
C13B	0.0147 (5)	0.0215 (5)	0.0164 (5)	0.0044 (4)	0.0003 (4)	−0.0004 (4)

Geometric parameters (Å, º) top

C1A—O1A	1.2364 (14)	C1B—O1B	1.2369 (14)
C1A—N1A	1.3475 (14)	C1B—N1B	1.3529 (14)
C1A—C2A	1.4964 (14)	C1B—C2B	1.4997 (14)
C2A—C7A	1.3932 (15)	C2B—C3B	1.3931 (15)
C2A—C3A	1.3963 (15)	C2B—C7B	1.4035 (15)
C3A—C4A	1.3875 (15)	C3B—C4B	1.3920 (15)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.3933 (17)	C4B—C5B	1.3876 (16)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.3884 (17)	C5B—C6B	1.3921 (17)
C5A—Cl1A	1.7364 (10)	C5B—Cl1B	1.7394 (11)
C6A—C7A	1.3939 (15)	C6B—C7B	1.3872 (16)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—H7A	0.9500	C7B—H7B	0.9500
N1A—C8A	1.4178 (13)	N1B—C8B	1.4194 (13)
N1A—H1NA	0.847 (18)	N1B—H1NB	0.887 (18)
C8A—C9A	1.3874 (15)	C8B—C9B	1.3936 (16)
C8A—C13A	1.4033 (16)	C8B—C13B	1.4023 (16)
C9A—C10A	1.3980 (14)	C9B—C10B	1.3987 (14)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—O2A	1.3697 (14)	C10B—O2B	1.3711 (14)
C10A—C11A	1.3908 (17)	C10B—C11B	1.3891 (17)
O2A—C14A	1.4281 (14)	O2B—C14B	1.4295 (13)
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C11A—C12A	1.3938 (17)	C11B—C12B	1.3936 (17)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.3869 (16)	C12B—C13B	1.3900 (16)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500

O1A—C1A—N1A	123.52 (10)	O1B—C1B—N1B	123.15 (10)
O1A—C1A—C2A	120.13 (10)	O1B—C1B—C2B	120.68 (10)
N1A—C1A—C2A	116.35 (10)	N1B—C1B—C2B	116.17 (10)
C7A—C2A—C3A	119.22 (10)	C3B—C2B—C7B	119.56 (10)
C7A—C2A—C1A	122.94 (10)	C3B—C2B—C1B	122.27 (10)
C3A—C2A—C1A	117.79 (10)	C7B—C2B—C1B	118.12 (10)
C4A—C3A—C2A	120.86 (10)	C4B—C3B—C2B	120.73 (10)
C4A—C3A—H3A	119.6	C4B—C3B—H3B	119.6
C2A—C3A—H3A	119.6	C2B—C3B—H3B	119.6
C3A—C4A—C5A	118.82 (11)	C5B—C4B—C3B	118.56 (11)
C3A—C4A—H4A	120.6	C5B—C4B—H4B	120.7
C5A—C4A—H4A	120.6	C3B—C4B—H4B	120.7
C6A—C5A—C4A	121.50 (10)	C4B—C5B—C6B	121.96 (10)
C6A—C5A—Cl1A	119.34 (9)	C4B—C5B—Cl1B	118.60 (9)
C4A—C5A—Cl1A	119.16 (9)	C6B—C5B—Cl1B	119.43 (9)
C5A—C6A—C7A	118.81 (10)	C7B—C6B—C5B	118.88 (10)
C5A—C6A—H6A	120.6	C7B—C6B—H6B	120.6
C7A—C6A—H6A	120.6	C5B—C6B—H6B	120.6
C2A—C7A—C6A	120.76 (10)	C6B—C7B—C2B	120.27 (11)
C2A—C7A—H7A	119.6	C6B—C7B—H7B	119.9
C6A—C7A—H7A	119.6	C2B—C7B—H7B	119.9
C1A—N1A—C8A	126.89 (10)	C1B—N1B—C8B	126.59 (10)
C1A—N1A—H1NA	117.8 (11)	C1B—N1B—H1NB	118.6 (11)
C8A—N1A—H1NA	115.3 (11)	C8B—N1B—H1NB	114.8 (11)
C9A—C8A—C13A	120.19 (10)	C9B—C8B—C13B	120.13 (10)
C9A—C8A—N1A	122.76 (10)	C9B—C8B—N1B	122.83 (10)
C13A—C8A—N1A	117.00 (10)	C13B—C8B—N1B	117.02 (10)
C8A—C9A—C10A	119.48 (10)	C8B—C9B—C10B	119.33 (10)
C8A—C9A—H9A	120.3	C8B—C9B—H9B	120.3
C10A—C9A—H9A	120.3	C10B—C9B—H9B	120.3
O2A—C10A—C11A	124.65 (10)	O2B—C10B—C11B	124.39 (10)
O2A—C10A—C9A	114.22 (10)	O2B—C10B—C9B	114.35 (10)
C11A—C10A—C9A	121.10 (10)	C11B—C10B—C9B	121.25 (11)
C10A—O2A—C14A	117.59 (9)	C10B—O2B—C14B	117.69 (9)
O2A—C14A—H14A	109.5	O2B—C14B—H14D	109.5
O2A—C14A—H14B	109.5	O2B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
O2A—C14A—H14C	109.5	O2B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C10A—C11A—C12A	118.56 (10)	C10B—C11B—C12B	118.61 (10)
C10A—C11A—H11A	120.7	C10B—C11B—H11B	120.7
C12A—C11A—H11A	120.7	C12B—C11B—H11B	120.7
C13A—C12A—C11A	121.37 (11)	C13B—C12B—C11B	121.37 (11)
C13A—C12A—H12A	119.3	C13B—C12B—H12B	119.3
C11A—C12A—H12A	119.3	C11B—C12B—H12B	119.3
C12A—C13A—C8A	119.27 (10)	C12B—C13B—C8B	119.31 (11)
C12A—C13A—H13A	120.4	C12B—C13B—H13B	120.3
C8A—C13A—H13A	120.4	C8B—C13B—H13B	120.3

O1A—C1A—C2A—C7A	−146.54 (12)	O1B—C1B—C2B—C3B	147.65 (12)
N1A—C1A—C2A—C7A	33.66 (15)	N1B—C1B—C2B—C3B	−32.96 (15)
O1A—C1A—C2A—C3A	30.77 (16)	O1B—C1B—C2B—C7B	−29.90 (15)
N1A—C1A—C2A—C3A	−149.03 (11)	N1B—C1B—C2B—C7B	149.49 (10)
C7A—C2A—C3A—C4A	−1.76 (17)	C7B—C2B—C3B—C4B	−0.84 (17)
C1A—C2A—C3A—C4A	−179.17 (10)	C1B—C2B—C3B—C4B	−178.36 (10)
C2A—C3A—C4A—C5A	1.56 (17)	C2B—C3B—C4B—C5B	−0.79 (17)
C3A—C4A—C5A—C6A	−0.02 (17)	C3B—C4B—C5B—C6B	1.13 (17)
C3A—C4A—C5A—Cl1A	−179.20 (9)	C3B—C4B—C5B—Cl1B	−179.70 (9)
C4A—C5A—C6A—C7A	−1.29 (17)	C4B—C5B—C6B—C7B	0.20 (18)
Cl1A—C5A—C6A—C7A	177.90 (9)	Cl1B—C5B—C6B—C7B	−178.97 (9)
C3A—C2A—C7A—C6A	0.41 (16)	C5B—C6B—C7B—C2B	−1.86 (17)
C1A—C2A—C7A—C6A	177.69 (10)	C3B—C2B—C7B—C6B	2.19 (16)
C5A—C6A—C7A—C2A	1.08 (17)	C1B—C2B—C7B—C6B	179.81 (10)
O1A—C1A—N1A—C8A	1.95 (19)	O1B—C1B—N1B—C8B	−3.85 (18)
C2A—C1A—N1A—C8A	−178.25 (10)	C2B—C1B—N1B—C8B	176.77 (10)
C1A—N1A—C8A—C9A	−24.49 (17)	C1B—N1B—C8B—C9B	22.32 (17)
C1A—N1A—C8A—C13A	157.99 (11)	C1B—N1B—C8B—C13B	−159.27 (11)
C13A—C8A—C9A—C10A	−0.46 (16)	C13B—C8B—C9B—C10B	0.94 (17)
N1A—C8A—C9A—C10A	−177.90 (10)	N1B—C8B—C9B—C10B	179.31 (10)
C8A—C9A—C10A—O2A	179.44 (10)	C8B—C9B—C10B—O2B	−179.68 (10)
C8A—C9A—C10A—C11A	1.42 (17)	C8B—C9B—C10B—C11B	−1.12 (17)
C11A—C10A—O2A—C14A	−7.68 (17)	C11B—C10B—O2B—C14B	−4.22 (17)
C9A—C10A—O2A—C14A	174.37 (10)	C9B—C10B—O2B—C14B	174.29 (10)
O2A—C10A—C11A—C12A	−178.57 (11)	O2B—C10B—C11B—C12B	178.73 (12)
C9A—C10A—C11A—C12A	−0.76 (17)	C9B—C10B—C11B—C12B	0.32 (18)
C10A—C11A—C12A—C13A	−0.87 (18)	C10B—C11B—C12B—C13B	0.67 (19)
C11A—C12A—C13A—C8A	1.81 (18)	C11B—C12B—C13B—C8B	−0.83 (18)
C9A—C8A—C13A—C12A	−1.13 (17)	C9B—C8B—C13B—C12B	0.01 (17)
N1A—C8A—C13A—C12A	176.46 (10)	N1B—C8B—C13B—C12B	−178.44 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1NB···O1A	0.887 (18)	1.977 (18)	2.8638 (13)	176.4 (15)
C3B—H3B···O1A	0.95	2.44	3.0436 (14)	121
C4B—H4B···O2A	0.95	2.59	3.5134 (15)	165
N1A—H1NA···O1Bⁱ	0.847 (18)	1.989 (18)	2.8309 (13)	172.0 (16)
C6A—H6A···O2Bⁱ	0.95	2.48	3.3885 (15)	161
C7A—H7A···O1Bⁱ	0.95	2.57	3.1611 (14)	121

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO₂
M_r	261.70
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	91
a, b, c (Å)	9.6952 (4), 10.5671 (3), 24.3512 (8)
V (Å³)	2494.78 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.80 × 0.27 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.771, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	47170, 8997, 8334
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.776

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.087, 1.05
No. of reflections	8997
No. of parameters	336
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.26
Absolute structure	Flack (1983), 3581 Friedel pairs
Absolute structure parameter	0.59 (3)

Computer programs: , APEX2 (Bruker, 2006) and SAINT (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004) and PLATON (Spek, 2003).