N-(4-Chloro-phen-yl)-2,2-diphenyl-acetamide.

In the title compound, C(20)H(16)ClNO, an S(6) ring motif is formed via an intra-molecular C-H⋯O hydrogen bond. The chloro-substituted benzene ring is almost perpendicular to the benzene rings, forming dihedral angles of 87.33 (9) and 88.69 (9)°. The dihedral angle between the benzene rings is 87.17 (9)°. In the crystal, mol-ecules are linked into chains parallel to the c axis by inter-molecular N-H⋯O hydrogen bonds. The crystal packing also features weak C-H⋯π inter-actions involving the chloro-substituted ring.

Related literature

For related structures, see: Fun et al. (2012a ▶,b ▶,c ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H16ClNO

M = 321.79

Monoclinic,

a = 10.2147 (2) Å

b = 17.8203 (4) Å

c = 9.5730 (2) Å

β = 114.019 (1)°

V = 1591.68 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.49 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.890, T max = 0.954

14326 measured reflections

3639 independent reflections

3091 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.103

S = 1.09

3639 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032965/rz2793sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032965/rz2793Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032965/rz2793Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H16ClNO	F(000) = 672
Mr = 321.79	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8307 reflections
a = 10.2147 (2) Å	θ = 2.2–32.2°
b = 17.8203 (4) Å	µ = 0.24 mm−1
c = 9.5730 (2) Å	T = 100 K
β = 114.019 (1)°	Block, colourless
V = 1591.68 (6) Å3	0.49 × 0.27 × 0.19 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3639 independent reflections
Radiation source: fine-focus sealed tube	3091 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.890, Tmax = 0.954	k = −21→23
14326 measured reflections	l = −12→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0323P)2 + 1.4338P] where P = (Fo2 + 2Fc2)/3
3639 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Cl1	1.15388 (5)	0.49276 (3)	1.29695 (5)	0.02582 (13)
O1	0.61313 (13)	0.26955 (7)	0.78711 (13)	0.0207 (3)
N1	0.64271 (15)	0.29804 (8)	1.03055 (16)	0.0164 (3)
H1N1	0.614 (2)	0.2863 (12)	1.098 (3)	0.027 (6)*
C1	0.2968 (2)	0.32265 (11)	0.7336 (2)	0.0228 (4)
H1A	0.3761	0.3418	0.7169	0.027*
C2	0.1669 (2)	0.36130 (12)	0.6756 (2)	0.0315 (5)
H2A	0.1578	0.4064	0.6194	0.038*
C3	0.0508 (2)	0.33385 (12)	0.6999 (3)	0.0352 (5)
H3A	−0.0377	0.3602	0.6609	0.042*
C4	0.0645 (2)	0.26804 (12)	0.7810 (2)	0.0310 (5)
H4A	−0.0149	0.2491	0.7977	0.037*
C5	0.19353 (19)	0.22950 (11)	0.8381 (2)	0.0237 (4)
H5A	0.2017	0.1842	0.8932	0.028*
C6	0.31158 (18)	0.25666 (10)	0.81530 (19)	0.0179 (4)
C7	0.37110 (18)	0.12810 (10)	0.6510 (2)	0.0182 (4)
H7A	0.3131	0.1676	0.5905	0.022*
C8	0.37547 (19)	0.05950 (10)	0.5837 (2)	0.0211 (4)
H8A	0.3202	0.0525	0.4774	0.025*
C9	0.45962 (19)	0.00140 (10)	0.6702 (2)	0.0213 (4)
H9A	0.4622	−0.0453	0.6235	0.026*
C10	0.54027 (19)	0.01183 (10)	0.8258 (2)	0.0206 (4)
H10A	0.5984	−0.0277	0.8859	0.025*
C11	0.53563 (18)	0.08021 (10)	0.8931 (2)	0.0184 (4)
H11A	0.5907	0.0870	0.9996	0.022*
C12	0.45162 (17)	0.13905 (10)	0.80713 (19)	0.0158 (3)
C13	0.45186 (17)	0.21313 (10)	0.88570 (18)	0.0156 (3)
H13A	0.4669	0.2009	0.9931	0.019*
C14	0.57806 (17)	0.26222 (10)	0.89552 (19)	0.0155 (3)
C15	0.76050 (17)	0.34768 (10)	1.08061 (19)	0.0160 (3)
C16	0.84756 (18)	0.36106 (10)	1.0026 (2)	0.0192 (4)
H16A	0.8252	0.3391	0.9052	0.023*
C17	0.96742 (18)	0.40692 (10)	1.0687 (2)	0.0206 (4)
H17A	1.0280	0.4158	1.0170	0.025*
C18	0.99832 (18)	0.43946 (10)	1.2094 (2)	0.0199 (4)
C19	0.90983 (19)	0.42853 (10)	1.2855 (2)	0.0209 (4)
H19A	0.9307	0.4521	1.3812	0.025*
C20	0.79109 (18)	0.38303 (10)	1.2206 (2)	0.0193 (4)
H20A	0.7295	0.3757	1.2717	0.023*

	U11	U22	U33	U12	U13	U23
Cl1	0.0203 (2)	0.0244 (2)	0.0292 (3)	−0.00523 (17)	0.00640 (18)	−0.00464 (19)
O1	0.0268 (6)	0.0253 (7)	0.0134 (6)	−0.0066 (5)	0.0119 (5)	−0.0035 (5)
N1	0.0188 (7)	0.0221 (8)	0.0115 (7)	−0.0028 (6)	0.0095 (6)	−0.0009 (6)
C1	0.0239 (9)	0.0212 (9)	0.0236 (9)	0.0012 (7)	0.0100 (7)	−0.0002 (8)
C2	0.0332 (11)	0.0235 (10)	0.0336 (12)	0.0061 (8)	0.0093 (9)	0.0002 (9)
C3	0.0239 (10)	0.0314 (12)	0.0446 (13)	0.0058 (8)	0.0080 (9)	−0.0130 (10)
C4	0.0225 (9)	0.0328 (11)	0.0396 (12)	−0.0054 (8)	0.0148 (9)	−0.0146 (10)
C5	0.0244 (9)	0.0228 (10)	0.0262 (10)	−0.0050 (7)	0.0126 (8)	−0.0062 (8)
C6	0.0197 (8)	0.0191 (9)	0.0154 (8)	−0.0015 (7)	0.0078 (7)	−0.0064 (7)
C7	0.0217 (8)	0.0189 (9)	0.0155 (8)	0.0005 (7)	0.0090 (7)	0.0022 (7)
C8	0.0264 (9)	0.0232 (10)	0.0154 (8)	−0.0031 (7)	0.0101 (7)	−0.0035 (7)
C9	0.0268 (9)	0.0177 (9)	0.0248 (9)	−0.0017 (7)	0.0161 (8)	−0.0033 (7)
C10	0.0228 (9)	0.0185 (9)	0.0234 (9)	0.0021 (7)	0.0125 (7)	0.0046 (7)
C11	0.0202 (8)	0.0214 (9)	0.0146 (8)	−0.0019 (7)	0.0081 (7)	0.0004 (7)
C12	0.0178 (8)	0.0170 (8)	0.0163 (8)	−0.0030 (6)	0.0107 (7)	−0.0006 (7)
C13	0.0199 (8)	0.0185 (9)	0.0101 (8)	−0.0016 (7)	0.0079 (6)	0.0005 (7)
C14	0.0183 (8)	0.0161 (8)	0.0133 (8)	0.0016 (6)	0.0077 (6)	0.0010 (7)
C15	0.0169 (8)	0.0166 (8)	0.0136 (8)	0.0009 (6)	0.0053 (6)	0.0006 (7)
C16	0.0231 (9)	0.0217 (9)	0.0147 (8)	−0.0005 (7)	0.0095 (7)	−0.0012 (7)
C17	0.0202 (8)	0.0229 (9)	0.0205 (9)	−0.0012 (7)	0.0102 (7)	−0.0001 (8)
C18	0.0164 (8)	0.0168 (9)	0.0226 (9)	−0.0002 (7)	0.0041 (7)	−0.0003 (7)
C19	0.0230 (9)	0.0224 (9)	0.0160 (9)	0.0009 (7)	0.0068 (7)	−0.0054 (7)
C20	0.0206 (8)	0.0228 (9)	0.0168 (9)	0.0008 (7)	0.0099 (7)	−0.0023 (7)

Cl1—C18	1.7451 (18)	C8—H8A	0.9500
O1—C14	1.2349 (19)	C9—C10	1.390 (3)
N1—C14	1.349 (2)	C9—H9A	0.9500
N1—C15	1.411 (2)	C10—C11	1.388 (3)
N1—H1N1	0.84 (2)	C10—H10A	0.9500
C1—C6	1.386 (3)	C11—C12	1.392 (2)
C1—C2	1.395 (3)	C11—H11A	0.9500
C1—H1A	0.9500	C12—C13	1.519 (2)
C2—C3	1.387 (3)	C13—C14	1.529 (2)
C2—H2A	0.9500	C13—H13A	1.0000
C3—C4	1.382 (3)	C15—C16	1.395 (2)
C3—H3A	0.9500	C15—C20	1.397 (2)
C4—C5	1.386 (3)	C16—C17	1.392 (2)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.396 (2)	C17—C18	1.380 (3)
C5—H5A	0.9500	C17—H17A	0.9500
C6—C13	1.524 (2)	C18—C19	1.386 (2)
C7—C8	1.391 (3)	C19—C20	1.379 (2)
C7—C12	1.396 (2)	C19—H19A	0.9500
C7—H7A	0.9500	C20—H20A	0.9500
C8—C9	1.385 (3)
C14—N1—C15	129.75 (14)	C10—C11—C12	121.05 (16)
C14—N1—H1N1	115.6 (15)	C10—C11—H11A	119.5
C15—N1—H1N1	114.4 (15)	C12—C11—H11A	119.5
C6—C1—C2	120.71 (18)	C11—C12—C7	118.73 (16)
C6—C1—H1A	119.6	C11—C12—C13	119.04 (15)
C2—C1—H1A	119.6	C7—C12—C13	122.23 (15)
C3—C2—C1	119.9 (2)	C12—C13—C6	114.31 (14)
C3—C2—H2A	120.0	C12—C13—C14	111.05 (13)
C1—C2—H2A	120.0	C6—C13—C14	110.69 (14)
C4—C3—C2	119.74 (19)	C12—C13—H13A	106.8
C4—C3—H3A	120.1	C6—C13—H13A	106.8
C2—C3—H3A	120.1	C14—C13—H13A	106.8
C3—C4—C5	120.29 (19)	O1—C14—N1	123.99 (16)
C3—C4—H4A	119.9	O1—C14—C13	122.31 (15)
C5—C4—H4A	119.9	N1—C14—C13	113.66 (14)
C4—C5—C6	120.65 (19)	C16—C15—C20	119.63 (16)
C4—C5—H5A	119.7	C16—C15—N1	124.52 (15)
C6—C5—H5A	119.7	C20—C15—N1	115.82 (15)
C1—C6—C5	118.67 (17)	C17—C16—C15	119.43 (16)
C1—C6—C13	123.22 (15)	C17—C16—H16A	120.3
C5—C6—C13	118.08 (16)	C15—C16—H16A	120.3
C8—C7—C12	120.19 (17)	C18—C17—C16	120.00 (16)
C8—C7—H7A	119.9	C18—C17—H17A	120.0
C12—C7—H7A	119.9	C16—C17—H17A	120.0
C9—C8—C7	120.61 (17)	C17—C18—C19	120.99 (16)
C9—C8—H8A	119.7	C17—C18—Cl1	119.93 (14)
C7—C8—H8A	119.7	C19—C18—Cl1	119.04 (14)
C8—C9—C10	119.58 (17)	C20—C19—C18	119.22 (16)
C8—C9—H9A	120.2	C20—C19—H19A	120.4
C10—C9—H9A	120.2	C18—C19—H19A	120.4
C11—C10—C9	119.83 (17)	C19—C20—C15	120.65 (16)
C11—C10—H10A	120.1	C19—C20—H20A	119.7
C9—C10—H10A	120.1	C15—C20—H20A	119.7
C6—C1—C2—C3	0.2 (3)	C5—C6—C13—C12	72.2 (2)
C1—C2—C3—C4	−0.3 (3)	C1—C6—C13—C14	16.8 (2)
C2—C3—C4—C5	0.1 (3)	C5—C6—C13—C14	−161.46 (15)
C3—C4—C5—C6	0.3 (3)	C15—N1—C14—O1	−1.8 (3)
C2—C1—C6—C5	0.2 (3)	C15—N1—C14—C13	−179.66 (16)
C2—C1—C6—C13	−178.09 (17)	C12—C13—C14—O1	43.3 (2)
C4—C5—C6—C1	−0.4 (3)	C6—C13—C14—O1	−84.76 (19)
C4—C5—C6—C13	177.91 (16)	C12—C13—C14—N1	−138.80 (15)
C12—C7—C8—C9	−0.1 (3)	C6—C13—C14—N1	93.11 (17)
C7—C8—C9—C10	0.1 (3)	C14—N1—C15—C16	−9.8 (3)
C8—C9—C10—C11	0.1 (3)	C14—N1—C15—C20	172.23 (17)
C9—C10—C11—C12	−0.3 (3)	C20—C15—C16—C17	2.8 (3)
C10—C11—C12—C7	0.2 (2)	N1—C15—C16—C17	−175.13 (16)
C10—C11—C12—C13	−179.13 (15)	C15—C16—C17—C18	−0.8 (3)
C8—C7—C12—C11	0.0 (2)	C16—C17—C18—C19	−1.4 (3)
C8—C7—C12—C13	179.30 (15)	C16—C17—C18—Cl1	176.51 (14)
C11—C12—C13—C6	−149.59 (15)	C17—C18—C19—C20	1.5 (3)
C7—C12—C13—C6	31.1 (2)	Cl1—C18—C19—C20	−176.42 (14)
C11—C12—C13—C14	84.30 (18)	C18—C19—C20—C15	0.6 (3)
C7—C12—C13—C14	−95.00 (18)	C16—C15—C20—C19	−2.7 (3)
C1—C6—C13—C12	−109.50 (18)	N1—C15—C20—C19	175.40 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.84 (2)	2.07 (2)	2.8598 (19)	157 (2)
C1—H1A···O1	0.95	2.58	3.202 (3)	123
C4—H4A···Cg1ii	0.95	2.93	3.415 (2)	113

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.84 (2)	2.07 (2)	2.8598 (19)	157 (2)
C1—H1A⋯O1	0.95	2.58	3.202 (3)	123
C4—H4A⋯Cg1ii	0.95	2.93	3.415 (2)	113

Symmetry codes: (i) ; (ii) .