2-Chloro-N-(4-nitro­phen­yl)acetamide

In the crystal structure of the title compound, C₈H₇ClN₂O₃, the mol­ecules are linked into chains by N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.101
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O14    -   N12     ..       6.08 su
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O14     ..       3.19 Ang.

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

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2004); software used to prepare material for publication: SHELXL97.

2-Chloro-N-(4-nitrophenyl)acetamide

Crystal data

C8H7ClN2O3	F(000) = 880
Mr = 214.61	Dx = 1.572 Mg m^−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.460 (1) Å	θ = 7.9–19.4°
b = 20.194 (3) Å	µ = 3.63 mm^−1
c = 9.496 (1) Å	T = 299 K
V = 1814.1 (4) Å^3	Laminar, colourless
Z = 8	0.33 × 0.30 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1294 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 67.0°, θmin = 4.4°
ω/θ scans	h = −11→7
Absorption correction: ψ scan (North et al., 1968)	k = −24→24
Tmin = 0.353, Tmax = 0.834	l = 0→11
5404 measured reflections	3 standard reflections every 120 min
1610 independent reflections	intensity decay: 3.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Only H-atom coordinates refined
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.4588P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
1610 reflections	Δρmax = 0.21 e Å^−3
149 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00073 (18)

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	0.69696 (6)	0.33767 (3)	0.82651 (6)	0.0635 (2)
O4	0.47554 (18)	0.23893 (8)	0.87619 (13)	0.0643 (5)
O13	0.0201 (2)	−0.02363 (10)	0.7765 (2)	0.0930 (6)
O14	0.08845 (19)	−0.05084 (8)	0.5679 (2)	0.0731 (5)
N5	0.45333 (18)	0.20516 (8)	0.64969 (15)	0.0419 (4)
H5N	0.479 (2)	0.2144 (11)	0.5668 (13)	0.050*
N12	0.0898 (2)	−0.01380 (9)	0.6700 (2)	0.0605 (5)
C2	0.5929 (3)	0.30093 (11)	0.6947 (2)	0.0521 (5)
H2A	0.528 (3)	0.3374 (12)	0.663 (2)	0.062*
H2B	0.653 (2)	0.2833 (12)	0.628 (3)	0.062*
C3	0.5028 (2)	0.24551 (9)	0.75120 (18)	0.0432 (4)
C6	0.3601 (2)	0.15160 (8)	0.66187 (18)	0.0407 (4)
C7	0.2936 (2)	0.13353 (10)	0.7869 (2)	0.0504 (5)
H7	0.312 (2)	0.1569 (11)	0.868 (3)	0.060*
C8	0.2025 (2)	0.08017 (11)	0.7878 (2)	0.0546 (5)
H8	0.154 (2)	0.0664 (12)	0.871 (3)	0.066*
C9	0.1805 (2)	0.04472 (10)	0.6666 (2)	0.0493 (5)
C10	0.2451 (2)	0.06187 (10)	0.5418 (2)	0.0534 (5)
H10	0.225 (2)	0.0377 (12)	0.460 (3)	0.064*
C11	0.3342 (2)	0.11531 (10)	0.5397 (2)	0.0501 (5)
H11	0.385 (2)	0.1272 (11)	0.455 (2)	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0608 (4)	0.0716 (4)	0.0582 (4)	−0.0085 (3)	−0.0108 (2)	−0.0127 (2)
O4	0.0977 (12)	0.0671 (9)	0.0279 (7)	−0.0204 (8)	0.0057 (7)	−0.0055 (6)
O13	0.0958 (15)	0.0871 (13)	0.0961 (15)	−0.0363 (11)	0.0117 (12)	0.0109 (11)
O14	0.0829 (12)	0.0505 (8)	0.0858 (12)	−0.0064 (8)	−0.0210 (10)	−0.0017 (8)
N5	0.0545 (10)	0.0467 (8)	0.0244 (7)	−0.0026 (7)	0.0018 (7)	0.0006 (6)
N12	0.0556 (12)	0.0514 (10)	0.0744 (13)	−0.0025 (8)	−0.0119 (10)	0.0152 (10)
C2	0.0614 (14)	0.0574 (11)	0.0374 (10)	−0.0112 (10)	−0.0029 (9)	−0.0009 (9)
C3	0.0528 (11)	0.0466 (9)	0.0303 (8)	0.0021 (8)	−0.0008 (8)	−0.0009 (7)
C6	0.0455 (11)	0.0421 (9)	0.0346 (9)	0.0044 (8)	−0.0023 (8)	0.0021 (7)
C7	0.0643 (14)	0.0497 (10)	0.0371 (10)	−0.0026 (10)	0.0069 (10)	−0.0008 (8)
C8	0.0610 (13)	0.0536 (11)	0.0493 (11)	0.0008 (10)	0.0079 (10)	0.0057 (9)
C9	0.0465 (11)	0.0432 (10)	0.0583 (12)	0.0015 (8)	−0.0067 (9)	0.0062 (9)
C10	0.0634 (13)	0.0518 (11)	0.0450 (10)	−0.0027 (10)	−0.0074 (10)	−0.0034 (9)
C11	0.0609 (13)	0.0541 (11)	0.0354 (10)	−0.0026 (9)	−0.0009 (9)	−0.0020 (8)

Geometric parameters (Å, º)

Cl1—C2	1.757 (2)	C6—C7	1.392 (3)
O4—C3	1.222 (2)	C6—C11	1.394 (2)
O13—N12	1.223 (3)	C7—C8	1.380 (3)
O14—N12	1.224 (2)	C7—H7	0.92 (2)
N5—C3	1.346 (2)	C8—C9	1.371 (3)
N5—C6	1.400 (2)	C8—H8	0.96 (2)
N5—H5N	0.845 (10)	C9—C10	1.378 (3)
N12—C9	1.460 (3)	C10—C11	1.369 (3)
C2—C3	1.506 (3)	C10—H10	0.93 (2)
C2—H2A	1.01 (2)	C11—H11	0.96 (2)
C2—H2B	0.93 (2)
C3—N5—C6	128.86 (15)	C11—C6—N5	116.64 (16)
C3—N5—H5N	115.7 (15)	C8—C7—C6	119.51 (19)
C6—N5—H5N	115.3 (15)	C8—C7—H7	120.8 (14)
O13—N12—O14	123.3 (2)	C6—C7—H7	119.7 (14)
O13—N12—C9	117.8 (2)	C9—C8—C7	119.8 (2)
O14—N12—C9	118.9 (2)	C9—C8—H8	118.0 (14)
C3—C2—Cl1	112.16 (14)	C7—C8—H8	122.2 (14)
C3—C2—H2A	107.7 (14)	C8—C9—C10	121.55 (19)
Cl1—C2—H2A	104.1 (13)	C8—C9—N12	119.53 (19)
C3—C2—H2B	108.0 (15)	C10—C9—N12	118.89 (19)
Cl1—C2—H2B	107.6 (15)	C11—C10—C9	118.92 (19)
H2A—C2—H2B	117 (2)	C11—C10—H10	121.8 (15)
O4—C3—N5	123.81 (18)	C9—C10—H10	119.3 (15)
O4—C3—C2	123.13 (17)	C10—C11—C6	120.72 (19)
N5—C3—C2	113.05 (15)	C10—C11—H11	120.8 (13)
C7—C6—C11	119.47 (18)	C6—C11—H11	118.3 (13)
C7—C6—N5	123.89 (16)
C6—N5—C3—O4	3.0 (3)	C7—C8—C9—N12	176.74 (19)
C6—N5—C3—C2	−175.58 (19)	O13—N12—C9—C8	10.5 (3)
Cl1—C2—C3—O4	18.9 (3)	O14—N12—C9—C8	−168.6 (2)
Cl1—C2—C3—N5	−162.54 (15)	O13—N12—C9—C10	−171.3 (2)
C3—N5—C6—C7	4.5 (3)	O14—N12—C9—C10	9.6 (3)
C3—N5—C6—C11	−175.70 (19)	C8—C9—C10—C11	0.5 (3)
C11—C6—C7—C8	−0.3 (3)	N12—C9—C10—C11	−177.63 (19)
N5—C6—C7—C8	179.47 (19)	C9—C10—C11—C6	0.5 (3)
C6—C7—C8—C9	1.3 (3)	C7—C6—C11—C10	−0.6 (3)
C7—C8—C9—C10	−1.4 (3)	N5—C6—C11—C10	179.63 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5N···O4^i	0.85 (1)	2.04 (1)	2.840 (2)	158 (2)

Symmetry code: (i) x, −y+1/2, z−1/2.