N-(2-Benzoyl-4-chloro­phenyl)-2-chloro­acet­amide

In the title compound, C₁₅H₁₁Cl₂NO₂, the aromatic rings are twisted by 62.2 (1)° and the chloro­acet­amide moiety adopts an extended conformation. Intramolecular N—H...O and N—H...Cl interactions stabilize the structure and networks of intermolecular C—H...O hydrogen bonds stabilize the crystal packing in addition to C—H...π and halogen–halogen interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.063
• wR factor = 0.160
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H18B   ..  CP      ..       2.81 Ang.

Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  Cl1     ..       3.35 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  O8      ..       2.69 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C18    ..  CP      ..       3.59 Ang.
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........         CP
                    H18B   CP
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........         CP
                    C18    CP
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........         CP
                    C18    H18B   CP
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C15 H11 Cl2 N O2

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003), ORTEP-3 (Farrugia, 1997) and ZORTEP (Zsolnai, 1998); software used to prepare material for publication: PLATON.

N-(2-Benzoyl-4-chlorophenyl)-2-chloroacetamide

Crystal data

C15H11Cl2NO2	Z = 2
Mr = 308.15	F(000) = 316
Triclinic, P1	Dx = 1.460 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9991 (15) Å	Cell parameters from 7815 reflections
b = 10.052 (3) Å	θ = 1.7–28.1°
c = 12.161 (3) Å	µ = 0.46 mm^−1
α = 81.391 (4)°	T = 293 K
β = 76.933 (4)°	Block, colorless
γ = 81.214 (4)°	0.30 × 0.25 × 0.22 mm
V = 700.9 (3) Å^3

Data collection

Siemens SMART CCD area-detector diffractometer	2362 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 28.1°, θmin = 1.7°
ω scans	h = −7→7
7815 measured reflections	k = −13→13
3135 independent reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 0.2942P] where P = (Fo^2 + 2Fc^2)/3
3135 reflections	(Δ/σ)max = 0.001
185 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.26088 (13)	0.61091 (8)	0.50393 (7)	0.0588 (3)
Cl2	−1.12836 (13)	0.73105 (8)	0.92397 (7)	0.0583 (3)
C1	−0.4852 (4)	0.6072 (3)	0.7645 (2)	0.0380 (6)
C2	−0.4295 (5)	0.7218 (3)	0.6859 (2)	0.0396 (6)
C3	−0.5952 (5)	0.8347 (3)	0.6800 (2)	0.0460 (7)
H3	−0.5610	0.9095	0.6271	0.055*
C4	−0.8086 (5)	0.8366 (3)	0.7518 (3)	0.0488 (7)
H4	−0.9177	0.9125	0.7470	0.059*
C5	−0.8613 (5)	0.7260 (3)	0.8308 (2)	0.0418 (6)
C6	−0.7029 (5)	0.6116 (3)	0.8368 (2)	0.0409 (6)
H6	−0.7411	0.5370	0.8892	0.049*
C7	−0.3160 (4)	0.4836 (3)	0.7750 (2)	0.0393 (6)
O8	−0.1084 (3)	0.4912 (2)	0.7528 (2)	0.0549 (6)
C9	−0.3942 (4)	0.3473 (3)	0.8104 (2)	0.0373 (6)
C10	−0.2589 (5)	0.2489 (3)	0.8683 (2)	0.0463 (7)
H10	−0.1377	0.2733	0.8938	0.056*
C11	−0.3024 (6)	0.1164 (3)	0.8881 (3)	0.0558 (8)
H11	−0.2140	0.0521	0.9290	0.067*
C12	−0.4767 (6)	0.0785 (3)	0.8475 (3)	0.0585 (8)
H12	−0.5030	−0.0118	0.8588	0.070*
C13	−0.6127 (5)	0.1754 (3)	0.7898 (3)	0.0534 (8)
H13	−0.7308	0.1497	0.7626	0.064*
C14	−0.5750 (5)	0.3091 (3)	0.7722 (2)	0.0435 (7)
H14	−0.6695	0.3739	0.7350	0.052*
N15	−0.2091 (4)	0.7174 (2)	0.6158 (2)	0.0439 (6)
C16	−0.1348 (6)	0.7992 (3)	0.5193 (3)	0.0564 (8)
O17	−0.2480 (5)	0.8955 (3)	0.4795 (3)	0.1115 (13)
C18	0.1121 (6)	0.7681 (3)	0.4585 (3)	0.0640 (9)
H18A	0.1967	0.8397	0.4666	0.077*
H18B	0.1147	0.7711	0.3781	0.077*
H15	−0.110 (5)	0.651 (3)	0.637 (2)	0.035 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0498 (5)	0.0647 (5)	0.0539 (5)	0.0077 (4)	−0.0075 (3)	−0.0023 (4)
Cl2	0.0419 (4)	0.0680 (5)	0.0596 (5)	0.0055 (4)	−0.0020 (3)	−0.0165 (4)
C1	0.0353 (13)	0.0394 (14)	0.0418 (14)	−0.0021 (11)	−0.0136 (11)	−0.0063 (11)
C2	0.0392 (14)	0.0406 (15)	0.0406 (14)	−0.0017 (11)	−0.0133 (11)	−0.0058 (11)
C3	0.0493 (16)	0.0382 (15)	0.0489 (16)	0.0013 (12)	−0.0122 (13)	−0.0036 (12)
C4	0.0462 (16)	0.0420 (16)	0.0588 (18)	0.0092 (12)	−0.0171 (14)	−0.0133 (13)
C5	0.0357 (14)	0.0483 (16)	0.0440 (15)	−0.0009 (12)	−0.0106 (11)	−0.0146 (12)
C6	0.0404 (14)	0.0409 (15)	0.0436 (15)	−0.0038 (11)	−0.0128 (12)	−0.0074 (11)
C7	0.0368 (14)	0.0432 (15)	0.0386 (14)	−0.0016 (11)	−0.0135 (11)	−0.0021 (11)
O8	0.0333 (10)	0.0498 (12)	0.0797 (15)	−0.0037 (9)	−0.0183 (10)	0.0067 (10)
C9	0.0343 (13)	0.0386 (14)	0.0353 (14)	0.0012 (11)	−0.0040 (11)	−0.0039 (10)
C10	0.0432 (15)	0.0518 (17)	0.0420 (15)	0.0007 (13)	−0.0114 (12)	−0.0022 (12)
C11	0.062 (2)	0.0458 (18)	0.0495 (17)	0.0053 (15)	−0.0077 (15)	0.0069 (13)
C12	0.067 (2)	0.0425 (17)	0.059 (2)	−0.0129 (15)	0.0008 (16)	0.0001 (14)
C13	0.0464 (17)	0.0561 (19)	0.0579 (19)	−0.0136 (14)	−0.0036 (14)	−0.0114 (14)
C14	0.0371 (14)	0.0440 (16)	0.0462 (16)	−0.0003 (12)	−0.0065 (12)	−0.0036 (12)
N15	0.0397 (13)	0.0430 (14)	0.0449 (13)	0.0024 (10)	−0.0099 (10)	0.0024 (10)
C16	0.0595 (19)	0.0516 (18)	0.0477 (17)	0.0091 (15)	−0.0057 (14)	0.0023 (14)
O17	0.091 (2)	0.104 (2)	0.084 (2)	0.0477 (18)	0.0182 (16)	0.0445 (17)
C18	0.064 (2)	0.063 (2)	0.0486 (18)	0.0091 (16)	0.0013 (15)	0.0082 (15)

Geometric parameters (Å, º)

Cl1—C18	1.769 (3)	C9—C14	1.396 (4)
Cl2—C5	1.739 (3)	C10—C11	1.372 (4)
C1—C6	1.399 (4)	C10—H10	0.9300
C1—C2	1.413 (4)	C11—C12	1.376 (5)
C1—C7	1.488 (4)	C11—H11	0.9300
C2—N15	1.400 (3)	C12—C13	1.386 (5)
C2—C3	1.394 (4)	C12—H12	0.9300
C3—C4	1.376 (4)	C13—C14	1.375 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.383 (4)	C14—H14	0.9300
C4—H4	0.9300	N15—C16	1.355 (4)
C5—C6	1.379 (4)	N15—H15	0.87 (3)
C6—H6	0.9300	C16—O17	1.200 (4)
C7—O8	1.225 (3)	C16—C18	1.507 (4)
C7—C9	1.487 (4)	C18—H18A	0.9700
C9—C10	1.391 (4)	C18—H18B	0.9700
C6—C1—C2	119.1 (2)	C11—C10—H10	119.6
C6—C1—C7	119.1 (2)	C12—C11—C10	120.1 (3)
C2—C1—C7	121.8 (2)	C12—C11—H11	119.9
N15—C2—C1	118.6 (2)	C10—C11—H11	119.9
N15—C2—C3	122.2 (3)	C13—C12—C11	119.7 (3)
C1—C2—C3	119.2 (3)	C13—C12—H12	120.1
C4—C3—C2	120.8 (3)	C11—C12—H12	120.1
C4—C3—H3	119.6	C12—C13—C14	120.7 (3)
C2—C3—H3	119.6	C12—C13—H13	119.7
C3—C4—C5	120.1 (3)	C14—C13—H13	119.7
C3—C4—H4	119.9	C13—C14—C9	119.7 (3)
C5—C4—H4	119.9	C13—C14—H14	120.1
C4—C5—C6	120.5 (3)	C9—C14—H14	120.1
C4—C5—Cl2	119.9 (2)	C16—N15—C2	128.6 (3)
C6—C5—Cl2	119.7 (2)	C16—N15—H15	116.9 (18)
C1—C6—C5	120.4 (3)	C2—N15—H15	114.5 (18)
C1—C6—H6	119.8	O17—C16—N15	125.5 (3)
C5—C6—H6	119.8	O17—C16—C18	117.3 (3)
O8—C7—C1	120.9 (2)	N15—C16—C18	117.2 (3)
O8—C7—C9	118.2 (2)	C16—C18—Cl1	116.5 (2)
C1—C7—C9	120.9 (2)	C16—C18—H18A	108.2
C10—C9—C14	119.0 (3)	Cl1—C18—H18A	108.2
C10—C9—C7	118.1 (2)	C16—C18—H18B	108.2
C14—C9—C7	122.1 (2)	Cl1—C18—H18B	108.2
C9—C10—C11	120.7 (3)	H18A—C18—H18B	107.3
C9—C10—H10	119.6
C6—C1—C2—N15	178.5 (2)	C1—C7—C9—C10	−150.8 (2)
C7—C1—C2—N15	0.5 (4)	O8—C7—C9—C14	−139.2 (3)
C6—C1—C2—C3	−1.9 (4)	C1—C7—C9—C14	39.6 (4)
C7—C1—C2—C3	−179.9 (2)	C14—C9—C10—C11	−0.3 (4)
N15—C2—C3—C4	−178.7 (3)	C7—C9—C10—C11	−170.2 (3)
C1—C2—C3—C4	1.7 (4)	C9—C10—C11—C12	2.1 (5)
C2—C3—C4—C5	0.0 (4)	C10—C11—C12—C13	−2.1 (5)
C3—C4—C5—C6	−1.5 (4)	C11—C12—C13—C14	0.2 (5)
C3—C4—C5—Cl2	178.1 (2)	C12—C13—C14—C9	1.6 (4)
C2—C1—C6—C5	0.4 (4)	C10—C9—C14—C13	−1.6 (4)
C7—C1—C6—C5	178.5 (2)	C7—C9—C14—C13	167.9 (3)
C4—C5—C6—C1	1.3 (4)	C1—C2—N15—C16	163.7 (3)
Cl2—C5—C6—C1	−178.3 (2)	C3—C2—N15—C16	−15.9 (5)
C6—C1—C7—O8	−149.3 (3)	C2—N15—C16—O17	3.2 (6)
C2—C1—C7—O8	28.8 (4)	C2—N15—C16—C18	−178.1 (3)
C6—C1—C7—C9	32.0 (4)	O17—C16—C18—Cl1	−169.6 (3)
C2—C1—C7—C9	−150.0 (3)	N15—C16—C18—Cl1	11.6 (4)
O8—C7—C9—C10	30.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N15—H15···Cl1	0.87 (3)	2.46 (3)	2.954 (2)	117 (2)
N15—H15···O8	0.87 (3)	1.97 (3)	2.686 (3)	138 (2)
C3—H3···O17^i	0.93	2.46	3.236 (4)	141
C14—H14···O8^ii	0.93	2.69	3.474 (3)	142
C18—H18B···Cp^iii	0.97	2.81	3.593 (5)	138

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