2,4,5-Tri­chloro­acetanilide

The title compound, C₈H₆Cl₃NO, also known as N-(2,4,5-tri­chloro­phenyl)­acet­amide, is an organic non-linear optical material. It crystallizes in the monoclinic system, in the non-centrosymmetric space group Pn.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.023
• wR factor = 0.062
• Data-to-parameter ratio = 16.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.03
         From the CIF: _reflns_number_total               1956
         Count of symmetry unique reflns         1139
         Completeness (_total/calc)            171.73%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       817
         Fraction of Friedel pairs measured     0.717
         Are heavy atom types Z>Si present          yes
          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.

---

Computing details

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

N-[2,4,5-trichlorophenyl]acetamide

Crystal data

C8H6Cl3NO	F(000) = 240
Mr = 238.49	Dx = 1.691 Mg m^−3
Monoclinic, Pn	Melting point: 464 K
Hall symbol: P -2yac	Mo Kα radiation, λ = 0.71073 Å
a = 3.9015 (8) Å	Cell parameters from 825 reflections
b = 12.658 (3) Å	θ = 3.9–27.7°
c = 9.6687 (19) Å	µ = 0.93 mm^−1
β = 101.186 (5)°	T = 293 K
V = 468.42 (17) Å^3	Needle, colourles
Z = 2	0.56 × 0.28 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1956 independent reflections
Radiation source: fine-focus sealed tube	1903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.624, Tmax = 0.787	k = −16→16
3931 measured reflections	l = −12→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0438P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
1956 reflections	Δρmax = 0.18 e Å^−3
119 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Absolute structure: (Flack, 1983), 817 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (4)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.39502 (10)	0.23324 (3)	0.52793 (4)	0.0478 (1)
Cl2	0.29487 (14)	0.52921 (3)	0.91216 (6)	0.0567 (2)
Cl3	0.08347 (11)	0.35322 (4)	1.11287 (5)	0.0523 (1)
O1	0.4013 (5)	0.00582 (11)	0.93830 (15)	0.0634 (5)
N1	0.1720 (4)	0.08189 (10)	0.72976 (14)	0.0377 (4)
C1	0.2040 (4)	0.18756 (11)	0.77550 (16)	0.0337 (4)
C2	0.3008 (4)	0.26574 (12)	0.69005 (17)	0.0355 (5)
C3	0.3274 (4)	0.37098 (13)	0.73118 (18)	0.0386 (4)
C4	0.2604 (4)	0.39830 (12)	0.86157 (18)	0.0375 (5)
C5	0.1658 (4)	0.32125 (13)	0.94911 (17)	0.0367 (4)
C6	0.1335 (4)	0.21694 (13)	0.90534 (18)	0.0367 (4)
C7	0.2734 (5)	−0.00256 (13)	0.81432 (18)	0.0386 (4)
C8	0.2160 (7)	−0.10773 (14)	0.7419 (2)	0.0533 (6)
H1	0.08262	0.07004	0.64265	0.0452*
H3	0.38949	0.42232	0.67176	0.0463*
H6	0.06375	0.16608	0.96358	0.0440*
H8A	0.34787	−0.16086	0.80013	0.0799*
H8B	0.29124	−0.10433	0.65319	0.0799*
H8C	−0.02790	−0.12529	0.72606	0.0799*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0664 (3)	0.0492 (2)	0.0301 (2)	−0.0091 (2)	0.0148 (2)	−0.0044 (2)
Cl2	0.0854 (3)	0.0338 (2)	0.0503 (3)	−0.0029 (2)	0.0121 (2)	−0.0071 (2)
Cl3	0.0778 (3)	0.0469 (2)	0.0354 (2)	0.0066 (2)	0.0191 (2)	−0.0052 (2)
O1	0.1068 (12)	0.0406 (6)	0.0321 (7)	0.0117 (7)	−0.0132 (7)	−0.0005 (5)
N1	0.0541 (7)	0.0315 (6)	0.0245 (7)	0.0007 (5)	0.0005 (5)	0.0001 (5)
C1	0.0399 (7)	0.0319 (7)	0.0268 (7)	0.0012 (5)	−0.0001 (6)	0.0024 (5)
C2	0.0409 (8)	0.0388 (8)	0.0256 (8)	−0.0019 (5)	0.0033 (6)	−0.0001 (6)
C3	0.0464 (8)	0.0358 (7)	0.0320 (8)	−0.0048 (6)	0.0039 (6)	0.0038 (6)
C4	0.0434 (8)	0.0310 (7)	0.0357 (9)	0.0013 (5)	0.0020 (6)	−0.0033 (5)
C5	0.0441 (8)	0.0369 (7)	0.0282 (8)	0.0053 (6)	0.0048 (6)	−0.0020 (6)
C6	0.0447 (8)	0.0355 (7)	0.0296 (8)	0.0018 (6)	0.0068 (6)	0.0035 (6)
C7	0.0498 (8)	0.0344 (7)	0.0295 (8)	0.0018 (6)	0.0026 (6)	0.0029 (6)
C8	0.0847 (13)	0.0340 (8)	0.0372 (10)	0.0040 (8)	0.0020 (9)	−0.0009 (6)

Geometric parameters (Å, º)

Cl1—C2	1.7277 (17)	C3—C4	1.380 (2)
Cl2—C4	1.7256 (16)	C4—C5	1.387 (2)
Cl3—C5	1.7237 (17)	C5—C6	1.385 (2)
O1—C7	1.210 (2)	C7—C8	1.501 (2)
N1—C1	1.4067 (19)	C3—H3	0.93
N1—C7	1.357 (2)	C6—H6	0.93
N1—H1	0.86	C8—H8A	0.96
C1—C6	1.387 (2)	C8—H8B	0.96
C1—C2	1.388 (2)	C8—H8C	0.96
C2—C3	1.388 (2)
Cl1···N1	2.9823 (16)	C2···Cl1^vi	3.6008 (19)
Cl1···C1^i	3.6186 (18)	C2···C1^i	3.599 (2)
Cl1···C2^i	3.6008 (19)	C2···C6^i	3.556 (2)
Cl1···Cl2^ii	3.6614 (10)	C3···C5^i	3.586 (2)
Cl1···C8^iii	3.617 (2)	C3···Cl2^ix	3.597 (2)
Cl2···C3^iv	3.597 (2)	C5···Cl3^i	3.6455 (19)
Cl2···Cl3^ii	3.6222 (11)	C5···C3^vi	3.586 (2)
Cl2···Cl3	3.1670 (10)	C6···O1	2.865 (2)
Cl2···Cl1^v	3.6614 (10)	C6···C2^vi	3.556 (2)
Cl3···C5^vi	3.6455 (19)	C8···O1^vii	3.223 (3)
Cl3···Cl2^v	3.6222 (11)	C8···Cl1^x	3.617 (2)
Cl3···Cl2	3.1670 (10)	C7···H6	2.7868
Cl1···H1	2.7400	C8···H8C^i	2.9917
Cl1···H8A^vii	2.9023	H1···Cl1	2.7400
Cl2···H3^iv	3.1304	H1···H8B	2.3478
Cl3···H3^v	3.0227	H1···O1^vii	2.1872
O1···C6	2.865 (2)	H3···Cl2^ix	3.1304
O1···N1^viii	3.022 (2)	H3···Cl3^ii	3.0227
O1···C8^viii	3.223 (3)	H6···O1	2.4564
O1···H6	2.4564	H6···C7	2.7868
O1···H1^viii	2.1872	H6···H8B^x	2.4204
O1···H8B^viii	2.6381	H8A···Cl1^viii	2.9023
N1···Cl1	2.9823 (16)	H8B···H1	2.3478
N1···O1^vii	3.022 (2)	H8B···O1^vii	2.6381
C1···Cl1^vi	3.6186 (18)	H8B···H6^iii	2.4204
C1···C2^vi	3.599 (2)	H8C···C8^vi	2.9917
C1—N1—C7	124.18 (14)	Cl3—C5—C6	118.84 (13)
C7—N1—H1	117.91	C1—C6—C5	120.66 (15)
C1—N1—H1	117.91	N1—C7—C8	114.71 (15)
N1—C1—C6	121.22 (14)	O1—C7—N1	122.92 (16)
N1—C1—C2	120.58 (14)	O1—C7—C8	122.37 (16)
C2—C1—C6	118.18 (14)	C2—C3—H3	120.49
C1—C2—C3	121.84 (15)	C4—C3—H3	120.48
Cl1—C2—C3	118.11 (12)	C1—C6—H6	119.67
Cl1—C2—C1	120.05 (12)	C5—C6—H6	119.66
C2—C3—C4	119.02 (15)	C7—C8—H8A	109.47
C3—C4—C5	120.07 (15)	C7—C8—H8B	109.47
Cl2—C4—C3	118.77 (12)	C7—C8—H8C	109.47
Cl2—C4—C5	121.16 (13)	H8A—C8—H8B	109.48
C4—C5—C6	120.20 (15)	H8A—C8—H8C	109.46
Cl3—C5—C4	120.95 (13)	H8B—C8—H8C	109.47
C7—N1—C1—C2	140.98 (18)	C1—C2—C3—C4	0.9 (2)
C7—N1—C1—C6	−40.3 (3)	Cl1—C2—C3—C4	−178.65 (12)
C1—N1—C7—O1	0.2 (3)	C2—C3—C4—Cl2	179.86 (12)
C1—N1—C7—C8	−179.58 (18)	C2—C3—C4—C5	−0.4 (2)
C2—C1—C6—C5	−1.2 (2)	Cl2—C4—C5—C6	178.82 (13)
N1—C1—C2—Cl1	−1.8 (2)	Cl2—C4—C5—Cl3	−0.7 (2)
C6—C1—C2—C3	−0.1 (2)	C3—C4—C5—C6	−0.9 (2)
N1—C1—C2—C3	178.64 (15)	C3—C4—C5—Cl3	179.59 (13)
C6—C1—C2—Cl1	179.46 (12)	C4—C5—C6—C1	1.7 (2)
N1—C1—C6—C5	−179.96 (15)	Cl3—C5—C6—C1	−178.73 (13)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^vii	0.86	2.19	3.022 (2)	164
C6—H6···O1	0.93	2.46	2.865 (2)	107

Symmetry code: (vii) x−1/2, −y, z−1/2.