4-Chloro-N-(2,6-dimethyl­phen­yl)benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808019120

4-Chloro-N-(2,6-dimethylphenyl)benzamide

B. T. Gowda, M. Tokarčík, J. Kožíšek, B. P. Sowmya and H. Fuess

The conformations of the N—H and C=O bonds in the structure of the title compound (N26DMP4CBA), C₁₅H₁₄ClNO, are anti to each other, similar to that observed in N-phenylbenzamide, N-(3,4-dimethylphenyl)benzamide, N-(2,6-dichlorophenyl)benzamide and other benzanilides. There are three molecules in the asymmetric unit of N26DMP4CBA. The central amide group is tilted with respect to the benzoyl ring by 45.2 (1)° in molecule 1, 21.2 (2)° in molecule 2 and 14.9 (2)° in molecule 3. The dihedral angles between the benzoyl and aniline rings are 39.9 (1), 51.0 (1) and 86.3 (3)° in molecules 1, 2 and 3, respectively. Intermolecular N—H

O hydrogen bonds link the molecules into infinite chains running along the [101] direction. One xylyl group is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808019120/dn2356sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808019120/dn2356Isup2.hkl Contains datablock I

CCDC reference: 696616

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.046
wR factor = 0.137
Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C49B   --  C50B    ..       7.49 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C29    --  C30     ..       7.02 su

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C42    --  C47     ..       5.53 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C53A   --  C54A    ..       6.61 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     --  C7      ..       5.49 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     --  C5      ..       5.80 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C32    --  C33     ..       5.47 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C52A
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C32
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C45
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C53A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C53B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C29
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C33
PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.10 Deg.
              C48A -N3   -C48B    1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         21

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  20 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
  19 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the present work, the structure of N-(2,6-dimethylphenyl)- 4-chlorobenzamide (N26DMP4CBA) has been determined to study the effect of substituents on the solid state geometries of benzanilides (Gowda et al., 2003, 2008a,b).

The conformations of the N—H and C=O bonds in N26DMP4CBA (Fig.1) are anti to each other, similar to that observed in N-(phenyl)-benzamide(NPBA)(Gowda et al., 2003), N-(3,4-dimethylphenyl)-benzamide (Gowda et al., 2008a), N-(2,6-dichlorophenyl)-benzamide and other benzanilides (Gowda et al., 2008b), with similar bond parameters. The amide group –NHCO– forms the dihedral angle of 45.2 (1)° in molecule 1, 21.2 (1)° in molecule 2, and 14.9 (2)° in molecule 3, with the benzoyl benzene ring. The dihedral angles between the benzoyl and aniline benzene rings are 39.9 (1)°, 51.0 (1)° and 86.3 (3)° in the molecule 1, 2 and 3, respectively.

The intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the [101] direction (Table 1).

Related literature top

For related literature, see: Gowda et al. (2003, 2008a,b).

Experimental top

The title compound was prepared according to the literature method (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. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. In molecule 3 only the A-component of the disordered xylyl ring is shown (atoms C48A to C55A). Hydrogen bonds are represented as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.

4-Chloro-N-(2,6-dimethylphenyl)benzamide top

Crystal data top

C₁₅H₁₄ClNO	Z = 6
M_r = 259.72	F(000) = 816
Triclinic, P1	D_x = 1.225 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.2696 (3) Å	Cell parameters from 16102 reflections
b = 13.6249 (4) Å	θ = 3.2–29.3°
c = 13.7981 (4) Å	µ = 0.26 mm⁻¹
α = 91.880 (2)°	T = 295 K
β = 113.623 (2)°	Block, colourless
γ = 90.3676 (18)°	0.49 × 0.22 × 0.13 mm
V = 2111.74 (10) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer	R_int = 0.042
Graphite monochromator	θ_max = 25.9°, θ_min = 5.6°
ω scans with κ offsets	h = −15→15
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction (2007); based on Clark & Reid (1995)]	k = −16→16
T_min = 0.896, T_max = 0.973	l = −16→16
63529 measured reflections	3 standard reflections every 120 min
8072 independent reflections	intensity decay: none
3945 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.0808P)²] where P = (F_o² + 2F_c²)/3
8072 reflections	(Δ/σ)_max = 0.027
543 parameters	Δρ_max = 0.21 e Å⁻³
21 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₄ClNO	γ = 90.3676 (18)°
M_r = 259.72	V = 2111.74 (10) Å³
Triclinic, P1	Z = 6
a = 12.2696 (3) Å	Mo Kα radiation
b = 13.6249 (4) Å	µ = 0.26 mm⁻¹
c = 13.7981 (4) Å	T = 295 K
α = 91.880 (2)°	0.49 × 0.22 × 0.13 mm
β = 113.623 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	3945 reflections with I > 2σ(I)
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction (2007); based on Clark & Reid (1995)]	R_int = 0.042
T_min = 0.896, T_max = 0.973	3 standard reflections every 120 min
63529 measured reflections	intensity decay: none
8072 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	21 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 0.89	Δρ_max = 0.21 e Å⁻³
8072 reflections	Δρ_min = −0.20 e Å⁻³
543 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	1.09618 (16)	0.27402 (14)	0.88857 (16)	0.0737 (5)
C2	1.11617 (15)	0.37750 (13)	0.86787 (15)	0.0690 (5)
C3	1.11340 (19)	0.45167 (17)	0.93676 (18)	0.0923 (6)
H3	1.0976	0.4366	0.9952	0.111*
C4	1.1337 (2)	0.54812 (18)	0.9205 (2)	0.1047 (7)
H4	1.1301	0.5980	0.9667	0.126*
C5	1.15906 (19)	0.56963 (16)	0.8358 (2)	0.0945 (7)
C6	1.16544 (19)	0.49792 (17)	0.7682 (2)	0.0946 (6)
H6	1.1849	0.5132	0.7118	0.114*
C7	1.14264 (17)	0.40178 (15)	0.78394 (18)	0.0824 (6)
H7	1.1453	0.3525	0.7367	0.099*
Cl1	1.18407 (8)	0.69118 (5)	0.81480 (8)	0.1603 (4)
O1	1.14255 (14)	0.24299 (11)	0.97876 (11)	0.1085 (5)
N1	1.02664 (13)	0.21731 (10)	0.80724 (12)	0.0711 (4)
H1	0.9923	0.2423	0.7462	0.085*
C8	1.00731 (18)	0.11569 (14)	0.81848 (14)	0.0736 (5)
C9	0.9194 (2)	0.08774 (18)	0.8511 (2)	0.0993 (7)
C10	0.9064 (3)	−0.0110 (3)	0.8638 (3)	0.1357 (10)
H10	0.8475	−0.0320	0.8852	0.163*
C11	0.9784 (4)	−0.0784 (2)	0.8456 (3)	0.1356 (11)
H11	0.9694	−0.1445	0.8562	0.163*
C12	1.0624 (3)	−0.04965 (18)	0.8124 (2)	0.1176 (8)
H12	1.1098	−0.0966	0.7990	0.141*
C13	1.0797 (2)	0.04760 (16)	0.79793 (17)	0.0884 (6)
C14	1.1743 (3)	0.0792 (2)	0.7626 (3)	0.1316 (9)
H14A	1.2201	0.0235	0.7589	0.197*
H14B	1.2254	0.1278	0.8122	0.197*
H14C	1.1380	0.1066	0.6940	0.197*
C15	0.8417 (3)	0.1628 (2)	0.8728 (3)	0.1510 (12)
H15A	0.7999	0.1982	0.8099	0.227*
H15B	0.8902	0.2079	0.9286	0.227*
H15C	0.7853	0.1302	0.8937	0.227*
C21	0.80003 (17)	0.33775 (13)	0.54313 (15)	0.0699 (5)
C22	0.77906 (16)	0.43964 (13)	0.50443 (14)	0.0673 (5)
C23	0.87450 (18)	0.50444 (15)	0.53812 (17)	0.0838 (6)
H23	0.9490	0.4827	0.5824	0.101*
C24	0.8632 (2)	0.59984 (15)	0.50858 (19)	0.0894 (6)
H24	0.9293	0.6421	0.5315	0.107*
C25	0.7536 (2)	0.63199 (14)	0.44497 (18)	0.0838 (6)
C26	0.6571 (2)	0.57051 (16)	0.41144 (19)	0.0985 (7)
H26	0.5824	0.5936	0.3693	0.118*
C27	0.66980 (18)	0.47394 (14)	0.43985 (17)	0.0870 (6)
H27	0.6038	0.4316	0.4151	0.104*
Cl2	0.73859 (7)	0.75296 (4)	0.40748 (7)	0.1292 (3)
O2	0.88901 (13)	0.32078 (10)	0.62217 (11)	0.1040 (5)
N2	0.72097 (12)	0.26782 (10)	0.48919 (12)	0.0700 (4)
H2	0.6619	0.2834	0.4326	0.084*
C28	0.72888 (16)	0.16867 (13)	0.52006 (14)	0.0687 (5)
C29	0.81179 (19)	0.10850 (16)	0.50619 (17)	0.0857 (6)
C30	0.8150 (2)	0.01226 (19)	0.5342 (2)	0.1094 (8)
H30	0.8703	−0.0293	0.5251	0.131*
C31	0.7402 (3)	−0.0228 (2)	0.5742 (2)	0.1215 (9)
H31	0.7445	−0.0879	0.5933	0.146*
C32	0.6578 (3)	0.0365 (2)	0.5871 (2)	0.1237 (9)
H32	0.6058	0.0113	0.6145	0.148*
C33	0.6504 (2)	0.13410 (16)	0.56004 (18)	0.0921 (6)
C34	0.5566 (3)	0.2008 (2)	0.5709 (3)	0.1433 (11)
H34A	0.5941	0.2601	0.6097	0.215*
H34B	0.5164	0.1678	0.6079	0.215*
H34C	0.5000	0.2166	0.5018	0.215*
C35	0.8955 (2)	0.1461 (2)	0.4599 (3)	0.1335 (10)
H35A	0.9490	0.1945	0.5079	0.200*
H35B	0.8506	0.1753	0.3935	0.200*
H35C	0.9402	0.0926	0.4487	0.200*
C41	0.44189 (18)	0.23143 (15)	0.21886 (17)	0.0803 (6)
C42	0.44517 (16)	0.12663 (14)	0.18302 (16)	0.0729 (5)
C43	0.52129 (19)	0.06379 (18)	0.25365 (19)	0.0930 (6)
H43	0.5689	0.0876	0.3217	0.112*
C44	0.5291 (2)	−0.03250 (19)	0.2268 (2)	0.0990 (7)
H44	0.5801	−0.0739	0.2764	0.119*
C45	0.4612 (2)	−0.06729 (16)	0.1265 (2)	0.0927 (7)
C46	0.3847 (2)	−0.00681 (19)	0.0540 (2)	0.1044 (7)
H46	0.3386	−0.0308	−0.0143	0.125*
C47	0.37655 (19)	0.08965 (16)	0.08270 (18)	0.0908 (6)
H47	0.3238	0.1305	0.0336	0.109*
Cl3	0.47088 (8)	−0.18837 (5)	0.09012 (8)	0.1440 (3)
O3	0.51840 (14)	0.26464 (11)	0.30151 (14)	0.1222 (6)
N3	0.35416 (14)	0.28586 (12)	0.15755 (12)	0.0789 (5)
H3A	0.2954	0.2589	0.1050	0.095*
C48A	0.3568 (7)	0.3855 (3)	0.1777 (7)	0.080 (2)	0.56
C49A	0.4260 (6)	0.4483 (3)	0.1473 (6)	0.098 (3)	0.56
C50A	0.4161 (5)	0.5494 (3)	0.1565 (5)	0.115 (2)	0.56
H50A	0.4624	0.5914	0.1361	0.138*	0.56
C51A	0.3369 (6)	0.5877 (3)	0.1962 (5)	0.124 (3)	0.56
H51A	0.3303	0.6554	0.2024	0.149*	0.56
C52A	0.2676 (7)	0.5249 (5)	0.2267 (7)	0.139 (3)	0.56
H52A	0.2146	0.5506	0.2533	0.167*	0.56
C53A	0.2776 (8)	0.4238 (4)	0.2175 (8)	0.106 (3)	0.56
C54A	0.1967 (18)	0.3545 (10)	0.2438 (17)	0.162 (7)	0.56
H54A	0.1444	0.3920	0.2663	0.243*	0.56
H54B	0.2441	0.3132	0.2997	0.243*	0.56
H54C	0.1505	0.3144	0.1822	0.243*	0.56
C55A	0.5035 (12)	0.4070 (8)	0.0937 (10)	0.142 (4)	0.56
H55A	0.5495	0.3543	0.1339	0.213*	0.56
H55B	0.5561	0.4578	0.0899	0.213*	0.56
H55C	0.4540	0.3827	0.0235	0.213*	0.56
C48B	0.3277 (9)	0.3861 (3)	0.1819 (9)	0.077 (3)	0.44
C49B	0.3888 (8)	0.4653 (5)	0.1647 (8)	0.105 (4)	0.44
C50B	0.3633 (7)	0.5605 (4)	0.1870 (7)	0.104 (3)	0.44
H50B	0.4042	0.6135	0.1755	0.125*	0.44
C51B	0.2768 (7)	0.5765 (3)	0.2265 (6)	0.113 (3)	0.44
H51B	0.2597	0.6402	0.2415	0.135*	0.44
C52B	0.2157 (7)	0.4973 (5)	0.2438 (6)	0.113 (3)	0.44
H52B	0.1578	0.5080	0.2702	0.136*	0.44
C53B	0.2412 (8)	0.4021 (4)	0.2215 (8)	0.088 (3)	0.44
C54B	0.181 (2)	0.3162 (13)	0.244 (2)	0.134 (6)	0.44
H54D	0.2390	0.2753	0.2928	0.202*	0.44
H54E	0.1369	0.2792	0.1793	0.202*	0.44
H54F	0.1269	0.3389	0.2744	0.202*	0.44
C55B	0.4917 (12)	0.4440 (12)	0.1357 (13)	0.150 (8)	0.44
H55D	0.5192	0.5037	0.1172	0.226*	0.44
H55E	0.4669	0.3978	0.0765	0.226*	0.44
H55F	0.5549	0.4168	0.1949	0.226*	0.44

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0661 (11)	0.0725 (12)	0.0614 (13)	0.0051 (9)	0.0032 (10)	0.0065 (11)
C2	0.0613 (11)	0.0665 (12)	0.0607 (12)	0.0026 (8)	0.0054 (9)	−0.0017 (10)
C3	0.1087 (16)	0.0799 (15)	0.0766 (14)	0.0160 (12)	0.0249 (12)	0.0004 (12)
C4	0.1182 (18)	0.0728 (16)	0.0999 (19)	0.0190 (12)	0.0204 (15)	−0.0134 (13)
C5	0.0885 (15)	0.0657 (14)	0.1108 (19)	0.0000 (11)	0.0209 (14)	0.0015 (14)
C6	0.0960 (15)	0.0827 (16)	0.1026 (17)	−0.0163 (12)	0.0379 (13)	−0.0019 (14)
C7	0.0845 (13)	0.0668 (13)	0.0896 (16)	−0.0110 (10)	0.0296 (12)	−0.0121 (11)
Cl1	0.1757 (7)	0.0677 (4)	0.2189 (10)	−0.0112 (4)	0.0594 (7)	0.0131 (5)
O1	0.1175 (11)	0.0922 (10)	0.0698 (10)	−0.0058 (8)	−0.0114 (8)	0.0156 (8)
N1	0.0747 (9)	0.0635 (9)	0.0554 (9)	−0.0018 (7)	0.0051 (8)	0.0093 (7)
C8	0.0768 (12)	0.0604 (11)	0.0647 (12)	−0.0016 (10)	0.0080 (10)	0.0106 (9)
C9	0.0876 (15)	0.0877 (16)	0.1184 (18)	−0.0027 (13)	0.0357 (14)	0.0213 (13)
C10	0.127 (2)	0.107 (2)	0.176 (3)	−0.0205 (19)	0.061 (2)	0.036 (2)
C11	0.153 (3)	0.0748 (18)	0.156 (3)	−0.0189 (19)	0.037 (2)	0.0289 (17)
C12	0.139 (2)	0.0682 (16)	0.125 (2)	0.0077 (15)	0.0314 (18)	0.0068 (14)
C13	0.1003 (15)	0.0694 (14)	0.0826 (15)	0.0039 (12)	0.0230 (12)	0.0039 (11)
C14	0.156 (2)	0.110 (2)	0.159 (3)	0.0103 (17)	0.096 (2)	−0.0014 (18)
C15	0.1123 (19)	0.146 (3)	0.221 (4)	0.0118 (19)	0.092 (2)	0.027 (2)
C21	0.0672 (12)	0.0682 (12)	0.0614 (12)	−0.0022 (10)	0.0120 (10)	0.0061 (10)
C22	0.0677 (12)	0.0642 (11)	0.0611 (11)	0.0021 (9)	0.0163 (9)	0.0060 (9)
C23	0.0709 (12)	0.0728 (13)	0.0940 (15)	−0.0012 (10)	0.0177 (11)	0.0168 (11)
C24	0.0868 (15)	0.0723 (13)	0.1117 (17)	−0.0049 (11)	0.0422 (13)	0.0101 (12)
C25	0.1046 (17)	0.0592 (12)	0.0925 (15)	0.0109 (12)	0.0442 (13)	0.0084 (11)
C26	0.0864 (15)	0.0766 (15)	0.1070 (17)	0.0188 (13)	0.0113 (13)	0.0088 (12)
C27	0.0745 (13)	0.0665 (12)	0.0950 (15)	0.0021 (10)	0.0078 (11)	0.0054 (11)
Cl2	0.1546 (6)	0.0690 (4)	0.1770 (7)	0.0267 (4)	0.0777 (5)	0.0318 (4)
O2	0.0955 (10)	0.0762 (9)	0.0863 (10)	−0.0137 (7)	−0.0213 (8)	0.0215 (7)
N2	0.0625 (9)	0.0626 (9)	0.0647 (9)	0.0004 (7)	0.0044 (7)	0.0025 (7)
C28	0.0645 (11)	0.0619 (11)	0.0645 (11)	−0.0025 (9)	0.0106 (9)	−0.0037 (9)
C29	0.0812 (14)	0.0708 (14)	0.0922 (15)	0.0046 (11)	0.0215 (12)	0.0002 (11)
C30	0.1033 (18)	0.0782 (17)	0.126 (2)	0.0132 (13)	0.0247 (16)	−0.0065 (15)
C31	0.158 (3)	0.0688 (16)	0.124 (2)	−0.0065 (18)	0.041 (2)	0.0091 (15)
C32	0.159 (3)	0.093 (2)	0.133 (2)	−0.0378 (19)	0.075 (2)	−0.0056 (16)
C33	0.1031 (16)	0.0748 (14)	0.1024 (16)	−0.0176 (12)	0.0466 (14)	−0.0097 (12)
C34	0.143 (2)	0.123 (2)	0.202 (3)	−0.0182 (19)	0.112 (2)	−0.024 (2)
C35	0.1168 (19)	0.121 (2)	0.190 (3)	0.0149 (16)	0.090 (2)	−0.0027 (19)
C41	0.0716 (12)	0.0766 (14)	0.0727 (14)	−0.0032 (11)	0.0077 (11)	0.0093 (11)
C42	0.0620 (11)	0.0763 (13)	0.0718 (13)	−0.0028 (9)	0.0174 (10)	0.0110 (11)
C43	0.0879 (14)	0.0899 (16)	0.0858 (15)	0.0074 (12)	0.0180 (12)	0.0131 (13)
C44	0.0985 (16)	0.0877 (17)	0.112 (2)	0.0169 (13)	0.0414 (16)	0.0270 (15)
C45	0.0941 (16)	0.0712 (14)	0.127 (2)	0.0044 (12)	0.0588 (16)	0.0123 (15)
C46	0.1089 (17)	0.0920 (18)	0.1009 (18)	−0.0004 (14)	0.0314 (15)	−0.0131 (15)
C47	0.0871 (14)	0.0817 (15)	0.0867 (16)	0.0080 (11)	0.0168 (12)	0.0060 (12)
Cl3	0.1719 (7)	0.0809 (4)	0.1979 (8)	0.0112 (4)	0.0942 (6)	−0.0001 (4)
O3	0.1012 (11)	0.0939 (11)	0.1011 (11)	0.0008 (9)	−0.0326 (10)	−0.0029 (9)
N3	0.0770 (10)	0.0681 (10)	0.0653 (10)	−0.0031 (8)	0.0010 (8)	0.0020 (8)
C48A	0.062 (4)	0.095 (6)	0.058 (4)	−0.001 (3)	−0.002 (3)	0.008 (3)
C49A	0.065 (5)	0.064 (4)	0.135 (7)	0.003 (4)	0.010 (4)	0.004 (3)
C50A	0.106 (5)	0.088 (4)	0.126 (5)	0.012 (3)	0.021 (4)	0.011 (3)
C51A	0.161 (7)	0.081 (4)	0.102 (5)	0.030 (5)	0.025 (5)	−0.021 (4)
C52A	0.187 (9)	0.097 (6)	0.113 (5)	0.023 (6)	0.042 (5)	−0.031 (5)
C53A	0.117 (7)	0.087 (5)	0.095 (5)	−0.007 (4)	0.023 (5)	−0.006 (4)
C54A	0.24 (2)	0.134 (14)	0.136 (8)	0.050 (11)	0.096 (12)	−0.001 (10)
C55A	0.149 (7)	0.124 (6)	0.187 (11)	0.013 (5)	0.101 (8)	0.036 (6)
C48B	0.065 (5)	0.051 (5)	0.089 (6)	0.008 (3)	0.004 (4)	−0.006 (4)
C49B	0.080 (6)	0.114 (8)	0.099 (5)	−0.001 (5)	0.011 (4)	0.045 (6)
C50B	0.113 (6)	0.047 (4)	0.118 (7)	−0.011 (4)	0.011 (5)	0.013 (4)
C51B	0.129 (7)	0.080 (6)	0.082 (5)	0.005 (5)	−0.005 (4)	−0.007 (4)
C52B	0.120 (6)	0.096 (6)	0.085 (5)	−0.003 (5)	0.004 (4)	−0.017 (4)
C53B	0.099 (7)	0.063 (5)	0.066 (5)	−0.005 (5)	−0.003 (4)	−0.015 (4)
C54B	0.150 (9)	0.121 (12)	0.168 (10)	−0.033 (10)	0.103 (8)	−0.025 (11)
C55B	0.157 (15)	0.160 (15)	0.139 (10)	−0.072 (13)	0.064 (10)	0.012 (8)

Geometric parameters (Å, º) top

C1—O1	1.233 (2)	C33—C34	1.522 (3)
C1—N1	1.323 (2)	C34—H34A	0.9600
C1—C2	1.486 (3)	C34—H34B	0.9600
C2—C7	1.372 (3)	C34—H34C	0.9600
C2—C3	1.374 (3)	C35—H35A	0.9600
C3—C4	1.378 (3)	C35—H35B	0.9600
C3—H3	0.9300	C35—H35C	0.9600
C4—C5	1.364 (3)	C41—O3	1.220 (2)
C4—H4	0.9300	C41—N3	1.321 (2)
C5—C6	1.353 (3)	C41—C42	1.502 (3)
C5—Cl1	1.737 (2)	C42—C43	1.375 (3)
C6—C7	1.380 (3)	C42—C47	1.376 (3)
C6—H6	0.9300	C43—C44	1.366 (3)
C7—H7	0.9300	C43—H43	0.9300
N1—C8	1.427 (2)	C44—C45	1.365 (3)
N1—H1	0.8600	C44—H44	0.9300
C8—C9	1.380 (3)	C45—C46	1.368 (3)
C8—C13	1.387 (3)	C45—Cl3	1.727 (2)
C9—C10	1.379 (4)	C46—C47	1.376 (3)
C9—C15	1.506 (4)	C46—H46	0.9300
C10—C11	1.364 (4)	C47—H47	0.9300
C10—H10	0.9300	N3—C48A	1.375 (4)
C11—C12	1.345 (4)	N3—C48B	1.465 (5)
C11—H11	0.9300	N3—H3A	0.8600
C12—C13	1.374 (3)	C48A—C49A	1.3900
C12—H12	0.9300	C48A—C53A	1.3900
C13—C14	1.493 (3)	C49A—C50A	1.3900
C14—H14A	0.9600	C49A—C55A	1.520 (10)
C14—H14B	0.9600	C50A—C51A	1.3900
C14—H14C	0.9600	C50A—H50A	0.9300
C15—H15A	0.9600	C51A—C52A	1.3900
C15—H15B	0.9600	C51A—H51A	0.9300
C15—H15C	0.9600	C52A—C53A	1.3900
C21—O2	1.225 (2)	C52A—H52A	0.9300
C21—N2	1.329 (2)	C53A—C54A	1.520 (10)
C21—C22	1.490 (2)	C54A—H54A	0.9600
C22—C27	1.374 (3)	C54A—H54B	0.9600
C22—C23	1.375 (3)	C54A—H54C	0.9600
C23—C24	1.366 (3)	C55A—H55A	0.9600
C23—H23	0.9300	C55A—H55B	0.9600
C24—C25	1.363 (3)	C55A—H55C	0.9600
C24—H24	0.9300	C48B—C49B	1.3900
C25—C26	1.357 (3)	C48B—C53B	1.3900
C25—Cl2	1.732 (2)	C49B—C50B	1.3900
C26—C27	1.377 (3)	C49B—C55B	1.497 (13)
C26—H26	0.9300	C50B—C51B	1.3900
C27—H27	0.9300	C50B—H50B	0.9300
N2—C28	1.422 (2)	C51B—C52B	1.3900
N2—H2	0.8600	C51B—H51B	0.9300
C28—C33	1.375 (3)	C52B—C53B	1.3900
C28—C29	1.378 (3)	C52B—H52B	0.9300
C29—C30	1.376 (3)	C53B—C54B	1.488 (13)
C29—C35	1.505 (3)	C54B—H54D	0.9600
C30—C31	1.340 (4)	C54B—H54E	0.9600
C30—H30	0.9300	C54B—H54F	0.9600
C31—C32	1.361 (4)	C55B—H55D	0.9600
C31—H31	0.9300	C55B—H55E	0.9600
C32—C33	1.386 (3)	C55B—H55F	0.9600
C32—H32	0.9300

O1—C1—N1	121.69 (18)	C33—C32—H32	119.6
O1—C1—C2	120.68 (17)	C28—C33—C32	117.9 (2)
N1—C1—C2	117.63 (16)	C28—C33—C34	120.5 (2)
C7—C2—C3	118.21 (19)	C32—C33—C34	121.6 (2)
C7—C2—C1	122.03 (18)	C33—C34—H34A	109.5
C3—C2—C1	119.7 (2)	C33—C34—H34B	109.5
C2—C3—C4	120.9 (2)	H34A—C34—H34B	109.5
C2—C3—H3	119.5	C33—C34—H34C	109.5
C4—C3—H3	119.5	H34A—C34—H34C	109.5
C5—C4—C3	119.3 (2)	H34B—C34—H34C	109.5
C5—C4—H4	120.4	C29—C35—H35A	109.5
C3—C4—H4	120.4	C29—C35—H35B	109.5
C6—C5—C4	121.1 (2)	H35A—C35—H35B	109.5
C6—C5—Cl1	119.5 (2)	C29—C35—H35C	109.5
C4—C5—Cl1	119.3 (2)	H35A—C35—H35C	109.5
C5—C6—C7	119.1 (2)	H35B—C35—H35C	109.5
C5—C6—H6	120.4	O3—C41—N3	121.64 (19)
C7—C6—H6	120.4	O3—C41—C42	120.69 (18)
C2—C7—C6	121.3 (2)	N3—C41—C42	117.67 (18)
C2—C7—H7	119.4	C43—C42—C47	117.8 (2)
C6—C7—H7	119.4	C43—C42—C41	118.59 (19)
C1—N1—C8	121.57 (15)	C47—C42—C41	123.64 (18)
C1—N1—H1	119.2	C44—C43—C42	121.9 (2)
C8—N1—H1	119.2	C44—C43—H43	119.0
C9—C8—C13	121.77 (19)	C42—C43—H43	119.0
C9—C8—N1	119.7 (2)	C45—C44—C43	119.3 (2)
C13—C8—N1	118.55 (19)	C45—C44—H44	120.4
C10—C9—C8	117.6 (3)	C43—C44—H44	120.4
C10—C9—C15	121.4 (3)	C44—C45—C46	120.4 (2)
C8—C9—C15	121.0 (2)	C44—C45—Cl3	120.2 (2)
C11—C10—C9	121.1 (3)	C46—C45—Cl3	119.4 (2)
C11—C10—H10	119.4	C45—C46—C47	119.6 (2)
C9—C10—H10	119.4	C45—C46—H46	120.2
C12—C11—C10	120.3 (3)	C47—C46—H46	120.2
C12—C11—H11	119.8	C46—C47—C42	121.0 (2)
C10—C11—H11	119.8	C46—C47—H47	119.5
C11—C12—C13	121.4 (3)	C42—C47—H47	119.5
C11—C12—H12	119.3	C41—N3—C48A	120.0 (4)
C13—C12—H12	119.3	C41—N3—C48B	126.6 (5)
C12—C13—C8	117.8 (2)	C48A—N3—C48B	15.1 (5)
C12—C13—C14	121.2 (2)	C41—N3—H3A	120.0
C8—C13—C14	121.0 (2)	C48A—N3—H3A	120.0
C13—C14—H14A	109.5	C48B—N3—H3A	111.7
C13—C14—H14B	109.5	N3—C48A—C49A	121.1 (4)
H14A—C14—H14B	109.5	N3—C48A—C53A	118.5 (4)
C13—C14—H14C	109.5	C49A—C48A—C53A	120.0
H14A—C14—H14C	109.5	C50A—C49A—C48A	120.0
H14B—C14—H14C	109.5	C50A—C49A—C55A	119.6 (5)
C9—C15—H15A	109.5	C48A—C49A—C55A	120.1 (5)
C9—C15—H15B	109.5	C49A—C50A—C51A	120.0
H15A—C15—H15B	109.5	C49A—C50A—H50A	120.0
C9—C15—H15C	109.5	C51A—C50A—H50A	120.0
H15A—C15—H15C	109.5	C50A—C51A—C52A	120.0
H15B—C15—H15C	109.5	C50A—C51A—H51A	120.0
O2—C21—N2	122.20 (17)	C52A—C51A—H51A	120.0
O2—C21—C22	119.60 (16)	C53A—C52A—C51A	120.0
N2—C21—C22	118.20 (16)	C53A—C52A—H52A	120.0
C27—C22—C23	117.79 (17)	C51A—C52A—H52A	120.0
C27—C22—C21	124.24 (17)	C52A—C53A—C48A	120.0
C23—C22—C21	117.94 (16)	C52A—C53A—C54A	120.4 (7)
C24—C23—C22	122.03 (19)	C48A—C53A—C54A	119.4 (7)
C24—C23—H23	119.0	C49B—C48B—C53B	120.0
C22—C23—H23	119.0	C49B—C48B—N3	119.8 (5)
C25—C24—C23	118.89 (19)	C53B—C48B—N3	120.2 (5)
C25—C24—H24	120.6	C48B—C49B—C50B	120.0
C23—C24—H24	120.6	C48B—C49B—C55B	117.9 (7)
C26—C25—C24	120.72 (19)	C50B—C49B—C55B	121.6 (7)
C26—C25—Cl2	120.13 (18)	C51B—C50B—C49B	120.0
C24—C25—Cl2	119.15 (17)	C51B—C50B—H50B	120.0
C25—C26—C27	119.9 (2)	C49B—C50B—H50B	120.0
C25—C26—H26	120.0	C52B—C51B—C50B	120.0
C27—C26—H26	120.0	C52B—C51B—H51B	120.0
C22—C27—C26	120.60 (19)	C50B—C51B—H51B	120.0
C22—C27—H27	119.7	C51B—C52B—C53B	120.0
C26—C27—H27	119.7	C51B—C52B—H52B	120.0
C21—N2—C28	123.50 (15)	C53B—C52B—H52B	120.0
C21—N2—H2	118.2	C52B—C53B—C48B	120.0
C28—N2—H2	118.2	C52B—C53B—C54B	120.7 (9)
C33—C28—C29	121.41 (19)	C48B—C53B—C54B	119.2 (9)
C33—C28—N2	118.86 (18)	C53B—C54B—H54D	109.4
C29—C28—N2	119.69 (18)	C53B—C54B—H54E	109.5
C30—C29—C28	118.3 (2)	H54D—C54B—H54E	109.5
C30—C29—C35	120.6 (2)	C53B—C54B—H54F	109.5
C28—C29—C35	121.2 (2)	H54D—C54B—H54F	109.5
C31—C30—C29	121.4 (3)	H54E—C54B—H54F	109.5
C31—C30—H30	119.3	C49B—C55B—H55D	109.5
C29—C30—H30	119.3	C49B—C55B—H55E	109.5
C30—C31—C32	120.3 (3)	H55D—C55B—H55E	109.5
C30—C31—H31	119.8	C49B—C55B—H55F	109.5
C32—C31—H31	119.8	H55D—C55B—H55F	109.5
C31—C32—C33	120.8 (3)	H55E—C55B—H55F	109.5
C31—C32—H32	119.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.02	2.8585 (19)	165
N2—H2···O3	0.86	1.96	2.778 (2)	158
N3—H3A···O1ⁱ	0.86	1.99	2.814 (2)	161

Symmetry code: (i) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClNO
M_r	259.72
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	12.2696 (3), 13.6249 (4), 13.7981 (4)
α, β, γ (°)	91.880 (2), 113.623 (2), 90.3676 (18)
V (Å³)	2111.74 (10)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.49 × 0.22 × 0.13

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction (2007); based on Clark & Reid (1995)]
T_min, T_max	0.896, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	63529, 8072, 3945
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 0.89
No. of reflections	8072
No. of parameters	543
No. of restraints	21
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).