2-Chloro-N-(3,5-dimethyl­phen­yl)acetamide

Gowda, B.T.; Foro, S.; Terao, H.; Fuess, H.

doi:10.1107/S160053680901304X

2-Chloro-N-(3,5-dimethylphenyl)acetamide

B. T. Gowda, S. Foro, H. Terao and H. Fuess

The conformation of the C=O bond in the structure of the title compound, C₁₀H₁₂ClNO, is anti to the N—H bond and to the C—Cl bond in the side chain in all four independent molecules comprising the asymmetric unit. In the crystal, intermolecular N—H

O hydrogen bonds link the molecules into supramolecular chains

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680901304X/tk2414sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680901304X/tk2414Isup2.hkl Contains datablock I

CCDC reference: 731272

checkCIF report

Key indicators

Single-crystal X-ray study
T = 299 K
Mean (C-C) = 0.006 Å
R factor = 0.050
wR factor = 0.164
Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem...          X
PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem...          S
PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem...          X
PLAT115_ALERT_5_B ADDSYM Detects Noncrystallographic Inversion ...         92 PerFi

Alert level C
            Value of measurement temperature given =   299.000
            Value of melting point given =     0.000
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.65
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     --  C8      ..       6.39 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C15    --  C20     ..       5.33 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

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           25.40
           From the CIF: _reflns_number_total               7450
           Count of symmetry unique reflns         3901
           Completeness (_total/calc)            190.98%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3549
           Fraction of Friedel pairs measured     0.910
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

In the present work, as part of a study of substituent effects on the crystal structures of aromatic amides (Gowda et al., 2008a,b,c), the structure of 2-chloro-N-(3,5-dimethylphenyl)acetamide (I) has been determined. The conformation of the C=O bond in (I) is anti to the N—H bond and to the C–Cl bond in the side chain (Fig. 1), in all the four independent molecules comprising the asymmetric unit. This is consistent with the anti conformation of the C=O bond to the N—H bond and to the side chain methylene H-atoms in 2-chloro-N- (2,4-dimethylphenyl)acetamide (Gowda et al., 2008a), in 2-chloro-N-(3,5-dichlorophenyl)acetamide (Gowda et al., 2008b), and in 2-chloro-N-(3-methylphenyl)acetamide (Gowda et al., 2008c). The molecules in (I) are linked into infinite chains through intermolecular N—H···O hydrogen bonding (Table 1, Fig. 2). There are two independent supramolecular chains, one comprising O2- and O3- containing molecules, and the other comprising O1- and O4-containing molecules.

Related literature top

For preparation of the compound, see: Shilpa & Gowda (2007). For related structures, see: Gowda et al. (2008a,b,c)

Experimental top

Compound (I) was prepared according to the literature method (Shilpa and Gowda, 2007). Single crystals were obtained from the slow evaporation of an ethanolic solution of (I).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); 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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2-Chloro-N-(3,5-dimethylphenyl)acetamide top

Crystal data top

C₁₀H₁₂ClNO	F(000) = 1664
M_r = 197.66	D_x = 1.289 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 7291 reflections
a = 25.9770 (1) Å	θ = 2.4–27.9°
b = 9.7698 (4) Å	µ = 0.34 mm⁻¹
c = 16.0578 (7) Å	T = 299 K
V = 4075.3 (3) Å³	Prism, colourless
Z = 16	0.45 × 0.42 × 0.30 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	7450 independent reflections
Radiation source: fine-focus sealed tube	4868 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Rotation method data acquisition using ω and ϕ scans	θ_max = 25.4°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −22→31
T_min = 0.864, T_max = 0.906	k = −11→11
27845 measured reflections	l = −19→19

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0756P)² + 2.0227P] where P = (F_o² + 2F_c²)/3
7450 reflections	(Δ/σ)_max = 0.041
478 parameters	Δρ_max = 0.53 e Å⁻³
1 restraint	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₀H₁₂ClNO	V = 4075.3 (3) Å³
M_r = 197.66	Z = 16
Orthorhombic, Pna2₁	Mo Kα radiation
a = 25.9770 (1) Å	µ = 0.34 mm⁻¹
b = 9.7698 (4) Å	T = 299 K
c = 16.0578 (7) Å	0.45 × 0.42 × 0.30 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	7450 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	4868 reflections with I > 2σ(I)
T_min = 0.864, T_max = 0.906	R_int = 0.021
27845 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.164	H-atom parameters constrained
S = 1.04	Δρ_max = 0.53 e Å⁻³
7450 reflections	Δρ_min = −0.20 e Å⁻³
478 parameters

Special details top

Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction Ltd., 2007 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.02134 (6)	0.25677 (12)	0.66479 (8)	0.0671 (5)
O1	0.06503 (10)	0.0729 (2)	0.5120 (2)	0.0537 (7)
N1	0.09129 (12)	0.2887 (3)	0.4815 (2)	0.0441 (8)
H1N	0.0825	0.3731	0.4867	0.053*
C1	0.13883 (16)	0.2643 (4)	0.4388 (3)	0.0380 (11)
C2	0.16416 (16)	0.3814 (4)	0.4133 (3)	0.0442 (10)
H2	0.1508	0.4672	0.4260	0.053*
C3	0.21023 (17)	0.3698 (4)	0.3679 (3)	0.0474 (10)
C4	0.22853 (18)	0.2446 (4)	0.3479 (4)	0.0517 (14)
H4	0.2583	0.2380	0.3160	0.062*
C5	0.20462 (16)	0.1281 (4)	0.3733 (3)	0.0490 (11)
C6	0.15811 (15)	0.1369 (4)	0.4183 (3)	0.0430 (10)
H6	0.1406	0.0579	0.4339	0.052*
C7	0.05941 (15)	0.1988 (3)	0.5138 (3)	0.0437 (9)
C8	0.01308 (17)	0.2590 (3)	0.5560 (3)	0.0366 (11)
H8A	−0.0173	0.2066	0.5412	0.044*
H8B	0.0081	0.3524	0.5372	0.044*
C9	0.2371 (2)	0.5040 (5)	0.3424 (4)	0.0793 (17)
H9A	0.2535	0.5438	0.3902	0.095*
H9B	0.2120	0.5667	0.3206	0.095*
H9C	0.2625	0.4850	0.3006	0.095*
C10	0.22586 (19)	−0.0168 (5)	0.3544 (4)	0.0706 (15)
H10A	0.2395	−0.0561	0.4046	0.085*
H10B	0.2526	−0.0104	0.3134	0.085*
H10C	0.1986	−0.0736	0.3336	0.085*
Cl2	0.27157 (5)	0.24330 (13)	0.66707 (8)	0.0662 (5)
O2	0.31648 (10)	0.0778 (2)	0.5114 (3)	0.0517 (8)
N2	0.34182 (11)	0.2954 (3)	0.4823 (2)	0.0370 (8)
H2N	0.3325	0.3792	0.4891	0.044*
C11	0.38852 (15)	0.2759 (4)	0.4382 (3)	0.0332 (10)
C12	0.41393 (15)	0.3947 (4)	0.4151 (3)	0.0412 (9)
H12	0.4006	0.4796	0.4300	0.049*
C13	0.45959 (17)	0.3868 (4)	0.3693 (3)	0.0487 (10)
C14	0.47836 (19)	0.2619 (4)	0.3459 (4)	0.0531 (14)
H14	0.5083	0.2569	0.3143	0.064*
C15	0.45357 (15)	0.1443 (4)	0.3686 (3)	0.0429 (10)
C16	0.40740 (15)	0.1502 (4)	0.4143 (3)	0.0422 (10)
H16	0.3899	0.0704	0.4282	0.051*
C17	0.31025 (13)	0.2014 (3)	0.5149 (3)	0.0354 (9)
C18	0.26418 (17)	0.2609 (3)	0.5580 (3)	0.0389 (12)
H18A	0.2333	0.2136	0.5400	0.047*
H18B	0.2607	0.3569	0.5437	0.047*
C19	0.48651 (18)	0.5228 (5)	0.3457 (4)	0.0703 (15)
H19A	0.5033	0.5601	0.3939	0.084*
H19B	0.4614	0.5867	0.3256	0.084*
H19C	0.5116	0.5058	0.3030	0.084*
C20	0.47403 (19)	0.0020 (5)	0.3456 (4)	0.0737 (16)
H20A	0.4897	−0.0392	0.3936	0.088*
H20B	0.4992	0.0104	0.3021	0.088*
H20C	0.4461	−0.0543	0.3267	0.088*
Cl3	0.14541 (5)	0.25313 (12)	−0.12686 (8)	0.0661 (5)
O3	0.19027 (10)	0.0786 (2)	0.0264 (3)	0.0508 (8)
N3	0.21661 (12)	0.2938 (3)	0.0580 (2)	0.0405 (8)
H3N	0.2081	0.3780	0.0510	0.049*
C21	0.26230 (16)	0.2724 (4)	0.1032 (3)	0.0392 (11)
C22	0.29014 (16)	0.3888 (4)	0.1253 (3)	0.0417 (10)
H22	0.2773	0.4742	0.1104	0.050*
C23	0.33499 (16)	0.3822 (4)	0.1676 (3)	0.0460 (11)
C24	0.35436 (17)	0.2513 (4)	0.1881 (4)	0.0460 (12)
H24	0.3855	0.2445	0.2165	0.055*
C25	0.32768 (16)	0.1304 (4)	0.1665 (3)	0.0485 (11)
C26	0.28151 (15)	0.1437 (4)	0.1241 (3)	0.0428 (10)
H26	0.2631	0.0658	0.1094	0.051*
C27	0.18431 (13)	0.2016 (3)	0.0241 (3)	0.0347 (9)
C28	0.13749 (17)	0.2653 (4)	−0.0172 (3)	0.0431 (13)
H28A	0.1343	0.3605	−0.0008	0.052*
H28B	0.1065	0.2173	−0.0001	0.052*
C29	0.36440 (18)	0.5045 (5)	0.1930 (4)	0.0651 (14)
H29A	0.3620	0.5157	0.2523	0.078*
H29B	0.3505	0.5839	0.1659	0.078*
H29C	0.3998	0.4935	0.1774	0.078*
C30	0.34979 (18)	−0.0028 (5)	0.1894 (4)	0.0693 (15)
H30A	0.3442	−0.0192	0.2477	0.083*
H30B	0.3861	−0.0024	0.1782	0.083*
H30C	0.3336	−0.0737	0.1575	0.083*
Cl4	−0.10462 (5)	0.26428 (12)	−0.12784 (7)	0.0655 (4)
O4	−0.05838 (10)	0.4286 (2)	0.0272 (2)	0.0571 (8)
N4	−0.03326 (12)	0.2113 (3)	0.0574 (2)	0.0445 (8)
H4N	−0.0418	0.1274	0.0491	0.053*
C31	0.01203 (16)	0.2306 (4)	0.1042 (3)	0.0386 (11)
C32	0.03858 (16)	0.1116 (3)	0.1258 (3)	0.0425 (10)
H32	0.0248	0.0276	0.1100	0.051*
C33	0.08350 (16)	0.1130 (4)	0.1687 (3)	0.0453 (10)
C34	0.10421 (17)	0.2418 (4)	0.1895 (4)	0.0451 (12)
H34	0.1352	0.2461	0.2185	0.054*
C35	0.07887 (16)	0.3651 (4)	0.1673 (3)	0.0461 (11)
C36	0.03352 (15)	0.3570 (4)	0.1245 (3)	0.0417 (9)
H36	0.0168	0.4369	0.1086	0.050*
C37	−0.06507 (14)	0.3041 (3)	0.0239 (3)	0.0431 (9)
C38	−0.11124 (18)	0.2462 (4)	−0.0188 (4)	0.0482 (14)
H38A	−0.1419	0.2938	−0.0002	0.058*
H38B	−0.1149	0.1502	−0.0047	0.058*
C39	0.11117 (17)	−0.0117 (5)	0.1926 (4)	0.0660 (14)
H39A	0.0964	−0.0889	0.1644	0.079*
H39B	0.1084	−0.0248	0.2517	0.079*
H39C	0.1468	−0.0031	0.1775	0.079*
C40	0.10289 (16)	0.4969 (4)	0.1907 (4)	0.0637 (14)
H40A	0.1392	0.4930	0.1799	0.076*
H40B	0.0972	0.5140	0.2488	0.076*
H40C	0.0878	0.5694	0.1585	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0814 (11)	0.0752 (9)	0.0446 (10)	0.0129 (6)	0.0047 (8)	−0.0048 (5)
O1	0.0556 (16)	0.0297 (11)	0.076 (2)	0.0029 (10)	0.0151 (15)	−0.0013 (14)
N1	0.0427 (18)	0.0332 (15)	0.056 (2)	0.0030 (14)	0.0042 (16)	0.0020 (16)
C1	0.036 (2)	0.043 (2)	0.035 (3)	0.0020 (15)	0.004 (2)	−0.0045 (16)
C2	0.048 (2)	0.042 (2)	0.043 (3)	0.0026 (17)	0.005 (2)	0.0010 (18)
C3	0.043 (2)	0.060 (2)	0.039 (2)	−0.0051 (19)	0.008 (2)	0.011 (2)
C4	0.039 (3)	0.074 (3)	0.042 (3)	−0.0030 (19)	0.007 (2)	−0.007 (2)
C5	0.045 (3)	0.057 (2)	0.046 (3)	0.011 (2)	0.000 (2)	−0.016 (2)
C6	0.038 (2)	0.042 (2)	0.049 (2)	−0.0028 (16)	0.002 (2)	−0.0036 (19)
C7	0.058 (2)	0.0292 (17)	0.044 (2)	0.0024 (16)	−0.003 (2)	0.0017 (17)
C8	0.040 (3)	0.0286 (18)	0.041 (3)	0.0029 (14)	0.007 (2)	0.0000 (14)
C9	0.075 (3)	0.080 (3)	0.082 (4)	−0.028 (3)	0.015 (3)	0.018 (3)
C10	0.063 (3)	0.062 (3)	0.086 (4)	0.009 (2)	0.014 (3)	−0.020 (3)
Cl2	0.0789 (11)	0.0734 (8)	0.0463 (11)	0.0040 (6)	0.0062 (8)	−0.0082 (6)
O2	0.0581 (18)	0.0239 (12)	0.073 (2)	0.0009 (10)	0.0153 (16)	0.0023 (15)
N2	0.0368 (18)	0.0249 (14)	0.049 (2)	0.0074 (13)	0.0089 (16)	0.0004 (15)
C11	0.035 (2)	0.0337 (17)	0.030 (2)	−0.0054 (16)	0.0045 (19)	−0.0030 (19)
C12	0.043 (2)	0.0389 (19)	0.042 (2)	−0.0022 (16)	0.005 (2)	0.0033 (19)
C13	0.047 (2)	0.062 (2)	0.037 (2)	−0.009 (2)	0.006 (2)	0.012 (2)
C14	0.046 (3)	0.076 (3)	0.037 (3)	−0.001 (2)	0.010 (2)	0.006 (2)
C15	0.042 (2)	0.048 (2)	0.039 (2)	0.0080 (18)	0.005 (2)	−0.012 (2)
C16	0.045 (2)	0.0350 (19)	0.046 (2)	0.0002 (18)	0.008 (2)	−0.001 (2)
C17	0.033 (2)	0.0329 (18)	0.040 (2)	0.0041 (15)	0.0011 (19)	0.004 (2)
C18	0.048 (3)	0.0302 (19)	0.038 (3)	0.0001 (15)	0.008 (2)	0.0064 (16)
C19	0.064 (3)	0.064 (3)	0.082 (4)	−0.028 (2)	0.013 (3)	0.025 (3)
C20	0.059 (3)	0.078 (3)	0.084 (4)	0.012 (2)	0.020 (3)	−0.020 (3)
Cl3	0.0835 (11)	0.0721 (8)	0.0427 (9)	0.0096 (6)	−0.0094 (8)	0.0089 (5)
O3	0.0581 (18)	0.0260 (13)	0.068 (2)	−0.0002 (11)	−0.0152 (16)	0.0001 (15)
N3	0.043 (2)	0.0245 (14)	0.054 (2)	−0.0015 (14)	−0.0095 (17)	0.0031 (16)
C21	0.039 (3)	0.037 (2)	0.042 (3)	0.0033 (17)	0.004 (2)	−0.0036 (19)
C22	0.046 (2)	0.0318 (19)	0.048 (3)	0.0019 (16)	−0.001 (2)	−0.0038 (19)
C23	0.046 (2)	0.047 (2)	0.045 (3)	−0.0093 (18)	0.006 (2)	−0.006 (2)
C24	0.035 (3)	0.067 (3)	0.035 (3)	−0.0035 (18)	−0.003 (2)	0.0056 (16)
C25	0.042 (2)	0.052 (2)	0.051 (3)	0.0017 (19)	0.002 (2)	0.006 (2)
C26	0.042 (2)	0.036 (2)	0.051 (3)	−0.0012 (17)	−0.002 (2)	0.004 (2)
C27	0.036 (2)	0.0241 (17)	0.044 (2)	−0.0050 (15)	−0.0027 (19)	0.0051 (19)
C28	0.039 (3)	0.0334 (19)	0.057 (4)	0.0014 (15)	−0.006 (2)	−0.0026 (19)
C29	0.064 (3)	0.069 (3)	0.062 (3)	−0.007 (2)	−0.011 (3)	−0.016 (3)
C30	0.060 (3)	0.062 (3)	0.086 (4)	0.011 (2)	−0.008 (3)	0.028 (3)
Cl4	0.0838 (11)	0.0709 (8)	0.0418 (9)	−0.0003 (6)	−0.0079 (8)	−0.0071 (7)
O4	0.0615 (17)	0.0299 (12)	0.080 (2)	−0.0013 (11)	−0.0212 (16)	0.0020 (14)
N4	0.0435 (19)	0.0326 (15)	0.058 (2)	0.0063 (14)	−0.0085 (16)	0.0005 (16)
C31	0.031 (2)	0.0413 (19)	0.043 (3)	−0.0044 (16)	0.0005 (19)	0.0042 (18)
C32	0.048 (2)	0.0290 (17)	0.050 (2)	0.0006 (16)	0.002 (2)	0.0017 (17)
C33	0.045 (2)	0.046 (2)	0.046 (3)	0.0091 (17)	0.004 (2)	0.0091 (19)
C34	0.037 (3)	0.061 (3)	0.038 (3)	0.0042 (17)	−0.004 (2)	−0.0050 (17)
C35	0.048 (2)	0.048 (2)	0.043 (3)	−0.0026 (18)	0.007 (2)	−0.005 (2)
C36	0.043 (2)	0.0360 (19)	0.046 (2)	0.0040 (17)	0.002 (2)	−0.0038 (19)
C37	0.054 (2)	0.0293 (17)	0.046 (2)	0.0011 (16)	−0.004 (2)	−0.0017 (17)
C38	0.046 (3)	0.041 (2)	0.058 (4)	−0.0049 (15)	−0.007 (3)	0.0045 (18)
C39	0.055 (3)	0.067 (3)	0.076 (4)	0.012 (2)	−0.005 (3)	0.021 (3)
C40	0.059 (3)	0.055 (3)	0.077 (3)	−0.012 (2)	−0.006 (3)	−0.023 (2)

Geometric parameters (Å, º) top

Cl1—C8	1.761 (5)	Cl3—C28	1.778 (6)
O1—C7	1.239 (4)	O3—C27	1.212 (4)
N1—C7	1.314 (5)	N3—C27	1.346 (4)
N1—C1	1.433 (5)	N3—C21	1.407 (5)
N1—H1N	0.8600	N3—H3N	0.8600
C1—C6	1.381 (5)	C21—C26	1.394 (5)
C1—C2	1.382 (5)	C21—C22	1.393 (5)
C2—C3	1.405 (6)	C22—C23	1.350 (6)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.351 (6)	C23—C24	1.413 (6)
C3—C9	1.540 (6)	C23—C29	1.476 (6)
C4—C5	1.360 (6)	C24—C25	1.413 (6)
C4—H4	0.9300	C24—H24	0.9300
C5—C6	1.410 (6)	C25—C26	1.385 (6)
C5—C10	1.549 (6)	C25—C30	1.469 (6)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.501 (6)	C27—C28	1.519 (6)
C8—H8A	0.9700	C28—H28A	0.9700
C8—H8B	0.9700	C28—H28B	0.9700
C9—H9A	0.9600	C29—H29A	0.9600
C9—H9B	0.9600	C29—H29B	0.9600
C9—H9C	0.9600	C29—H29C	0.9600
C10—H10A	0.9600	C30—H30A	0.9600
C10—H10B	0.9600	C30—H30B	0.9600
C10—H10C	0.9600	C30—H30C	0.9600
Cl2—C18	1.770 (5)	Cl4—C38	1.768 (6)
O2—C17	1.220 (4)	O4—C37	1.230 (3)
N2—C17	1.338 (4)	N4—C37	1.339 (4)
N2—C11	1.418 (5)	N4—C31	1.409 (5)
N2—H2N	0.8600	N4—H4N	0.8600
C11—C16	1.377 (5)	C31—C36	1.393 (5)
C11—C12	1.386 (5)	C31—C32	1.396 (5)
C12—C13	1.397 (6)	C32—C33	1.356 (6)
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.366 (6)	C33—C34	1.409 (6)
C13—C19	1.549 (6)	C33—C39	1.466 (6)
C14—C15	1.367 (5)	C34—C35	1.418 (6)
C14—H14	0.9300	C34—H34	0.9300
C15—C16	1.407 (5)	C35—C36	1.367 (6)
C15—C20	1.534 (5)	C35—C40	1.479 (5)
C16—H16	0.9300	C36—H36	0.9300
C17—C18	1.500 (6)	C37—C38	1.493 (6)
C18—H18A	0.9700	C38—H38A	0.9700
C18—H18B	0.9700	C38—H38B	0.9700
C19—H19A	0.9600	C39—H39A	0.9600
C19—H19B	0.9600	C39—H39B	0.9600
C19—H19C	0.9600	C39—H39C	0.9600
C20—H20A	0.9600	C40—H40A	0.9600
C20—H20B	0.9600	C40—H40B	0.9600
C20—H20C	0.9600	C40—H40C	0.9600

C7—N1—C1	128.4 (3)	C27—N3—C21	129.5 (3)
C7—N1—H1N	115.8	C27—N3—H3N	115.3
C1—N1—H1N	115.8	C21—N3—H3N	115.3
C6—C1—C2	120.2 (4)	C26—C21—C22	119.3 (4)
C6—C1—N1	125.2 (4)	C26—C21—N3	124.1 (4)
C2—C1—N1	114.5 (3)	C22—C21—N3	116.6 (3)
C1—C2—C3	119.5 (4)	C23—C22—C21	122.5 (4)
C1—C2—H2	120.3	C23—C22—H22	118.8
C3—C2—H2	120.3	C21—C22—H22	118.8
C4—C3—C2	119.7 (4)	C22—C23—C24	117.9 (4)
C4—C3—C9	123.2 (4)	C22—C23—C29	123.2 (4)
C2—C3—C9	117.1 (4)	C24—C23—C29	119.0 (4)
C3—C4—C5	121.8 (5)	C25—C24—C23	121.6 (4)
C3—C4—H4	119.1	C25—C24—H24	119.2
C5—C4—H4	119.1	C23—C24—H24	119.2
C4—C5—C6	119.6 (4)	C26—C25—C24	117.8 (4)
C4—C5—C10	122.9 (4)	C26—C25—C30	123.0 (4)
C6—C5—C10	117.5 (4)	C24—C25—C30	119.1 (4)
C1—C6—C5	119.2 (4)	C25—C26—C21	120.9 (4)
C1—C6—H6	120.4	C25—C26—H26	119.6
C5—C6—H6	120.4	C21—C26—H26	119.6
O1—C7—N1	125.5 (4)	O3—C27—N3	124.8 (4)
O1—C7—C8	119.6 (3)	O3—C27—C28	121.5 (3)
N1—C7—C8	114.9 (3)	N3—C27—C28	113.7 (3)
C7—C8—Cl1	110.2 (3)	C27—C28—Cl3	108.2 (3)
C7—C8—H8A	109.6	C27—C28—H28A	110.1
Cl1—C8—H8A	109.6	Cl3—C28—H28A	110.1
C7—C8—H8B	109.6	C27—C28—H28B	110.1
Cl1—C8—H8B	109.6	Cl3—C28—H28B	110.1
H8A—C8—H8B	108.1	H28A—C28—H28B	108.4
C3—C9—H9A	109.5	C23—C29—H29A	109.5
C3—C9—H9B	109.5	C23—C29—H29B	109.5
H9A—C9—H9B	109.5	H29A—C29—H29B	109.5
C3—C9—H9C	109.5	C23—C29—H29C	109.5
H9A—C9—H9C	109.5	H29A—C29—H29C	109.5
H9B—C9—H9C	109.5	H29B—C29—H29C	109.5
C5—C10—H10A	109.5	C25—C30—H30A	109.5
C5—C10—H10B	109.5	C25—C30—H30B	109.5
H10A—C10—H10B	109.5	H30A—C30—H30B	109.5
C5—C10—H10C	109.5	C25—C30—H30C	109.5
H10A—C10—H10C	109.5	H30A—C30—H30C	109.5
H10B—C10—H10C	109.5	H30B—C30—H30C	109.5
C17—N2—C11	128.9 (3)	C37—N4—C31	129.7 (3)
C17—N2—H2N	115.6	C37—N4—H4N	115.1
C11—N2—H2N	115.6	C31—N4—H4N	115.1
C16—C11—C12	120.2 (4)	C36—C31—C32	118.8 (4)
C16—C11—N2	124.3 (3)	C36—C31—N4	125.3 (4)
C12—C11—N2	115.4 (3)	C32—C31—N4	115.7 (3)
C11—C12—C13	119.9 (4)	C33—C32—C31	122.9 (4)
C11—C12—H12	120.1	C33—C32—H32	118.5
C13—C12—H12	120.1	C31—C32—H32	118.5
C14—C13—C12	119.8 (4)	C32—C33—C34	117.3 (4)
C14—C13—C19	122.5 (4)	C32—C33—C39	123.2 (4)
C12—C13—C19	117.7 (4)	C34—C33—C39	119.5 (4)
C13—C14—C15	120.6 (4)	C33—C34—C35	121.5 (4)
C13—C14—H14	119.7	C33—C34—H34	119.3
C15—C14—H14	119.7	C35—C34—H34	119.3
C14—C15—C16	120.4 (4)	C36—C35—C34	118.5 (4)
C14—C15—C20	122.3 (4)	C36—C35—C40	122.8 (4)
C16—C15—C20	117.3 (4)	C34—C35—C40	118.7 (4)
C11—C16—C15	119.0 (3)	C35—C36—C31	121.0 (4)
C11—C16—H16	120.5	C35—C36—H36	119.5
C15—C16—H16	120.5	C31—C36—H36	119.5
O2—C17—N2	125.5 (4)	O4—C37—N4	124.4 (4)
O2—C17—C18	120.7 (3)	O4—C37—C38	120.5 (3)
N2—C17—C18	113.8 (3)	N4—C37—C38	115.1 (3)
C17—C18—Cl2	109.4 (3)	C37—C38—Cl4	109.8 (3)
C17—C18—H18A	109.8	C37—C38—H38A	109.7
Cl2—C18—H18A	109.8	Cl4—C38—H38A	109.7
C17—C18—H18B	109.8	C37—C38—H38B	109.7
Cl2—C18—H18B	109.8	Cl4—C38—H38B	109.7
H18A—C18—H18B	108.2	H38A—C38—H38B	108.2
C13—C19—H19A	109.5	C33—C39—H39A	109.5
C13—C19—H19B	109.5	C33—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C13—C19—H19C	109.5	C33—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5
C15—C20—H20A	109.5	C35—C40—H40A	109.5
C15—C20—H20B	109.5	C35—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
C15—C20—H20C	109.5	C35—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5

C7—N1—C1—C6	5.1 (8)	C27—N3—C21—C26	−2.7 (8)
C7—N1—C1—C2	−178.9 (4)	C27—N3—C21—C22	175.1 (4)
C6—C1—C2—C3	−1.4 (7)	C26—C21—C22—C23	−1.0 (7)
N1—C1—C2—C3	−177.6 (4)	N3—C21—C22—C23	−178.9 (4)
C1—C2—C3—C4	1.7 (7)	C21—C22—C23—C24	1.4 (7)
C1—C2—C3—C9	−179.1 (5)	C21—C22—C23—C29	−178.7 (5)
C2—C3—C4—C5	−2.7 (8)	C22—C23—C24—C25	−0.9 (8)
C9—C3—C4—C5	178.2 (5)	C29—C23—C24—C25	179.1 (5)
C3—C4—C5—C6	3.2 (8)	C23—C24—C25—C26	0.1 (8)
C3—C4—C5—C10	−177.4 (5)	C23—C24—C25—C30	179.9 (5)
C2—C1—C6—C5	1.9 (7)	C24—C25—C26—C21	0.3 (7)
N1—C1—C6—C5	177.7 (4)	C30—C25—C26—C21	−179.6 (5)
C4—C5—C6—C1	−2.7 (7)	C22—C21—C26—C25	0.1 (7)
C10—C5—C6—C1	177.8 (5)	N3—C21—C26—C25	177.9 (5)
C1—N1—C7—O1	−0.7 (7)	C21—N3—C27—O3	−1.1 (7)
C1—N1—C7—C8	178.9 (5)	C21—N3—C27—C28	177.6 (5)
O1—C7—C8—Cl1	77.7 (4)	O3—C27—C28—Cl3	−74.7 (5)
N1—C7—C8—Cl1	−102.0 (3)	N3—C27—C28—Cl3	106.6 (4)
C17—N2—C11—C16	6.3 (7)	C37—N4—C31—C36	−0.8 (8)
C17—N2—C11—C12	−177.3 (4)	C37—N4—C31—C32	−175.9 (4)
C16—C11—C12—C13	−1.7 (7)	C36—C31—C32—C33	2.7 (7)
N2—C11—C12—C13	−178.2 (4)	N4—C31—C32—C33	178.2 (4)
C11—C12—C13—C14	1.5 (7)	C31—C32—C33—C34	−1.9 (7)
C11—C12—C13—C19	−179.6 (5)	C31—C32—C33—C39	179.1 (5)
C12—C13—C14—C15	−1.6 (8)	C32—C33—C34—C35	0.6 (8)
C19—C13—C14—C15	179.5 (5)	C39—C33—C34—C35	179.7 (4)
C13—C14—C15—C16	2.0 (8)	C33—C34—C35—C36	−0.3 (8)
C13—C14—C15—C20	−178.4 (5)	C33—C34—C35—C40	−179.6 (4)
C12—C11—C16—C15	2.0 (7)	C34—C35—C36—C31	1.1 (7)
N2—C11—C16—C15	178.2 (4)	C40—C35—C36—C31	−179.6 (5)
C14—C15—C16—C11	−2.2 (7)	C32—C31—C36—C35	−2.3 (7)
C20—C15—C16—C11	178.2 (5)	N4—C31—C36—C35	−177.3 (4)
C11—N2—C17—O2	−0.7 (7)	C31—N4—C37—O4	2.2 (7)
C11—N2—C17—C18	179.7 (4)	C31—N4—C37—C38	−177.3 (5)
O2—C17—C18—Cl2	73.2 (4)	O4—C37—C38—Cl4	72.7 (5)
N2—C17—C18—Cl2	−107.1 (3)	N4—C37—C38—Cl4	−107.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4ⁱ	0.86	2.14	2.983 (4)	168
N2—H2N···O3ⁱⁱ	0.86	2.12	2.975 (4)	171
N3—H3N···O2ⁱⁱⁱ	0.86	2.15	3.000 (4)	170
N4—H4N···O1^iv	0.86	2.13	2.987 (4)	172

Symmetry codes: (i) −x, −y+1, z+1/2; (ii) −x+1/2, y+1/2, z+1/2; (iii) −x+1/2, y+1/2, z−1/2; (iv) −x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂ClNO
M_r	197.66
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	299
a, b, c (Å)	25.9770 (1), 9.7698 (4), 16.0578 (7)
V (Å³)	4075.3 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.45 × 0.42 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.864, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	27845, 7450, 4868
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.164, 1.04
No. of reflections	7450
No. of parameters	478
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.20

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).