Crystal structure and Hirshfeld surface analysis of 2-(4-nitro­phen­yl)-2-oxoethyl 2-chloro­benzoate

The title compound, 2-(4-nitro­phen­yl)-2-oxoethyl 2-chloro­benzoate, is relatively planar with the two aromatic rings being inclined to each other by 3.56 (11)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.054
• wR factor = 0.141
• Data-to-parameter ratio = 20.7

checkCIF/PLATON results

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

2-(4-Nitrophenyl)-2-oxoethyl 2-chlorobenzoate

Crystal data

C15H10ClNO5	F(000) = 656
Mr = 319.69	Dx = 1.509 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6264 reflections
a = 12.6646 (18) Å	θ = 2.3–27.5°
b = 12.4099 (18) Å	µ = 0.30 mm^−1
c = 9.0902 (13) Å	T = 294 K
β = 99.947 (2)°	Block, colourless
V = 1407.2 (3) Å^3	0.55 × 0.26 × 0.19 mm
Z = 4

Data collection

Bruker APEXII DUO CCD area-detector diffractometer	4122 independent reflections
Radiation source: Rotating Anode	2586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 18.4 pixels mm^-1	θmax = 30.1°, θmin = 1.6°
φ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −17→17
Tmin = 0.796, Tmax = 0.946	l = −12→12
36449 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.141	W = 1/[Σ^2(FO^2) + (0.0456P)^2 + 0.8032P] WHERE P = (FO^2 + 2FC^2)/3
S = 1.06	(Δ/σ)max < 0.001
4122 reflections	Δρmax = 0.26 e Å^−3
199 parameters	Δρmin = −0.44 e Å^−3

Special details

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

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	0.13276 (6)	0.19871 (4)	0.64688 (9)	0.0704 (3)
O1	0.32241 (12)	0.43016 (11)	0.42430 (17)	0.0451 (5)
O2	0.44530 (13)	0.57459 (11)	0.32308 (19)	0.0553 (6)
O3	0.31616 (15)	0.26717 (12)	0.5238 (2)	0.0662 (7)
O4	0.8091 (3)	0.28826 (18)	−0.0648 (4)	0.1349 (15)
O5	0.8233 (2)	0.45298 (17)	−0.1127 (3)	0.1031 (10)
N1	0.78442 (18)	0.38048 (17)	−0.0532 (3)	0.0632 (8)
C1	0.60280 (16)	0.53537 (15)	0.1467 (2)	0.0378 (6)
C2	0.68013 (17)	0.51241 (15)	0.0615 (2)	0.0407 (6)
C3	0.70239 (17)	0.40590 (16)	0.0379 (2)	0.0432 (7)
C4	0.65143 (19)	0.32166 (16)	0.0961 (3)	0.0493 (7)
C5	0.57408 (18)	0.34589 (15)	0.1802 (3)	0.0458 (7)
C6	0.54870 (15)	0.45265 (14)	0.2066 (2)	0.0356 (6)
C7	0.46407 (16)	0.48220 (15)	0.2957 (2)	0.0367 (6)
C8	0.40417 (18)	0.38936 (16)	0.3492 (2)	0.0429 (6)
C9	0.28099 (17)	0.35666 (15)	0.5069 (2)	0.0394 (6)
C10	0.19286 (15)	0.40267 (15)	0.5758 (2)	0.0365 (6)
C11	0.12673 (17)	0.33809 (16)	0.6478 (2)	0.0414 (6)
C12	0.05046 (19)	0.3840 (2)	0.7205 (3)	0.0548 (8)
C13	0.0388 (2)	0.4942 (2)	0.7222 (3)	0.0604 (9)
C14	0.10067 (19)	0.55891 (18)	0.6499 (3)	0.0544 (8)
C15	0.17715 (17)	0.51397 (16)	0.5769 (3)	0.0443 (7)
H1	0.58650	0.60680	0.16450	0.0450*
H2	0.71620	0.56730	0.02110	0.0490*
H4	0.66890	0.25050	0.07900	0.0590*
H5	0.53830	0.29040	0.21980	0.0550*
H8A	0.37220	0.34550	0.26490	0.0510*
H8B	0.45330	0.34460	0.41680	0.0510*
H12	0.00710	0.34040	0.76810	0.0660*
H13	−0.01150	0.52480	0.77300	0.0720*
H14	0.09130	0.63320	0.64990	0.0650*
H15	0.21870	0.55860	0.52770	0.0530*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0741 (4)	0.0363 (3)	0.1119 (6)	−0.0032 (3)	0.0471 (4)	0.0109 (3)
O1	0.0529 (9)	0.0353 (7)	0.0540 (9)	0.0031 (6)	0.0285 (7)	0.0035 (6)
O2	0.0648 (11)	0.0323 (7)	0.0754 (11)	−0.0003 (7)	0.0311 (9)	−0.0077 (7)
O3	0.0755 (12)	0.0382 (8)	0.0983 (14)	0.0158 (8)	0.0524 (11)	0.0190 (8)
O4	0.165 (3)	0.0587 (13)	0.222 (3)	0.0172 (14)	0.149 (3)	−0.0060 (16)
O5	0.1241 (19)	0.0699 (13)	0.144 (2)	−0.0058 (13)	0.1036 (18)	0.0043 (13)
N1	0.0670 (14)	0.0509 (11)	0.0825 (16)	−0.0031 (10)	0.0433 (12)	−0.0073 (11)
C1	0.0436 (11)	0.0268 (8)	0.0437 (11)	−0.0021 (7)	0.0095 (9)	−0.0019 (8)
C2	0.0446 (11)	0.0342 (9)	0.0456 (12)	−0.0058 (8)	0.0141 (9)	0.0031 (8)
C3	0.0444 (12)	0.0394 (10)	0.0504 (13)	−0.0019 (9)	0.0214 (10)	−0.0037 (9)
C4	0.0588 (14)	0.0296 (9)	0.0659 (15)	−0.0004 (9)	0.0284 (12)	−0.0048 (9)
C5	0.0554 (13)	0.0288 (9)	0.0591 (14)	−0.0051 (9)	0.0268 (11)	−0.0009 (9)
C6	0.0393 (10)	0.0295 (8)	0.0392 (11)	−0.0031 (7)	0.0106 (9)	−0.0026 (8)
C7	0.0412 (11)	0.0320 (9)	0.0383 (11)	−0.0015 (8)	0.0105 (9)	−0.0013 (8)
C8	0.0517 (12)	0.0341 (9)	0.0486 (12)	0.0005 (8)	0.0250 (10)	−0.0021 (8)
C9	0.0428 (11)	0.0322 (9)	0.0458 (12)	−0.0011 (8)	0.0149 (9)	0.0010 (8)
C10	0.0355 (10)	0.0339 (9)	0.0410 (11)	0.0012 (7)	0.0089 (9)	0.0032 (8)
C11	0.0409 (11)	0.0368 (9)	0.0491 (12)	−0.0001 (8)	0.0149 (9)	0.0046 (9)
C12	0.0500 (13)	0.0566 (13)	0.0644 (16)	0.0006 (11)	0.0288 (12)	0.0066 (12)
C13	0.0540 (14)	0.0560 (14)	0.0790 (18)	0.0104 (11)	0.0336 (14)	−0.0026 (13)
C14	0.0537 (14)	0.0369 (11)	0.0762 (17)	0.0096 (9)	0.0214 (13)	−0.0022 (10)
C15	0.0456 (12)	0.0343 (10)	0.0553 (13)	0.0018 (8)	0.0150 (10)	0.0030 (9)

Geometric parameters (Å, º)

Cl1—C11	1.732 (2)	C10—C11	1.401 (3)
O1—C8	1.428 (3)	C10—C15	1.396 (3)
O1—C9	1.344 (2)	C11—C12	1.384 (3)
O2—C7	1.206 (2)	C12—C13	1.376 (4)
O3—C9	1.197 (2)	C13—C14	1.367 (4)
O4—N1	1.196 (3)	C14—C15	1.383 (3)
O5—N1	1.199 (3)	C1—H1	0.9300
N1—C3	1.470 (3)	C2—H2	0.9300
C1—C2	1.379 (3)	C4—H4	0.9300
C1—C6	1.396 (3)	C5—H5	0.9300
C2—C3	1.376 (3)	C8—H8A	0.9700
C3—C4	1.381 (3)	C8—H8B	0.9700
C4—C5	1.376 (3)	C12—H12	0.9300
C5—C6	1.394 (3)	C13—H13	0.9300
C6—C7	1.496 (3)	C14—H14	0.9300
C7—C8	1.506 (3)	C15—H15	0.9300
C9—C10	1.485 (3)
C8—O1—C9	114.31 (15)	C10—C11—C12	120.71 (19)
O4—N1—O5	123.0 (3)	C11—C12—C13	120.0 (2)
O4—N1—C3	118.4 (3)	C12—C13—C14	120.5 (2)
O5—N1—C3	118.6 (2)	C13—C14—C15	120.1 (2)
C2—C1—C6	120.74 (17)	C10—C15—C14	121.0 (2)
C1—C2—C3	118.07 (18)	C2—C1—H1	120.00
N1—C3—C2	118.53 (18)	C6—C1—H1	120.00
N1—C3—C4	118.41 (19)	C1—C2—H2	121.00
C2—C3—C4	123.1 (2)	C3—C2—H2	121.00
C3—C4—C5	118.17 (19)	C3—C4—H4	121.00
C4—C5—C6	120.72 (19)	C5—C4—H4	121.00
C1—C6—C5	119.24 (18)	C4—C5—H5	120.00
C1—C6—C7	118.47 (16)	C6—C5—H5	120.00
C5—C6—C7	122.29 (18)	O1—C8—H8A	110.00
O2—C7—C6	122.01 (18)	O1—C8—H8B	110.00
O2—C7—C8	122.19 (19)	C7—C8—H8A	110.00
C6—C7—C8	115.80 (16)	C7—C8—H8B	110.00
O1—C8—C7	109.30 (16)	H8A—C8—H8B	108.00
O1—C9—O3	121.9 (2)	C11—C12—H12	120.00
O1—C9—C10	111.65 (16)	C13—C12—H12	120.00
O3—C9—C10	126.36 (19)	C12—C13—H13	120.00
C9—C10—C11	122.06 (17)	C14—C13—H13	120.00
C9—C10—C15	120.13 (18)	C13—C14—H14	120.00
C11—C10—C15	117.74 (18)	C15—C14—H14	120.00
Cl1—C11—C10	122.61 (16)	C10—C15—H15	120.00
Cl1—C11—C12	116.66 (17)	C14—C15—H15	119.00
C9—O1—C8—C7	−164.95 (16)	C5—C6—C7—O2	177.1 (2)
C8—O1—C9—O3	5.3 (3)	C5—C6—C7—C8	−2.8 (3)
C8—O1—C9—C10	−177.15 (15)	O2—C7—C8—O1	3.6 (3)
O4—N1—C3—C2	174.8 (3)	C6—C7—C8—O1	−176.59 (15)
O4—N1—C3—C4	−5.1 (4)	O1—C9—C10—C11	170.13 (17)
O5—N1—C3—C2	−5.4 (3)	O1—C9—C10—C15	−13.2 (3)
O5—N1—C3—C4	174.7 (3)	O3—C9—C10—C11	−12.5 (3)
C6—C1—C2—C3	−0.2 (3)	O3—C9—C10—C15	164.3 (2)
C2—C1—C6—C5	0.4 (3)	C9—C10—C11—Cl1	−6.6 (3)
C2—C1—C6—C7	−178.83 (17)	C9—C10—C11—C12	175.2 (2)
C1—C2—C3—N1	179.79 (19)	C15—C10—C11—Cl1	176.60 (17)
C1—C2—C3—C4	−0.4 (3)	C15—C10—C11—C12	−1.6 (3)
N1—C3—C4—C5	−179.5 (2)	C9—C10—C15—C14	−175.3 (2)
C2—C3—C4—C5	0.7 (4)	C11—C10—C15—C14	1.6 (3)
C3—C4—C5—C6	−0.5 (4)	Cl1—C11—C12—C13	−178.1 (2)
C4—C5—C6—C1	0.0 (3)	C10—C11—C12—C13	0.2 (3)
C4—C5—C6—C7	179.2 (2)	C11—C12—C13—C14	1.3 (4)
C1—C6—C7—O2	−3.7 (3)	C12—C13—C14—C15	−1.3 (4)
C1—C6—C7—C8	176.42 (17)	C13—C14—C15—C10	−0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3^i	0.93	2.54	3.258 (2)	135
C8—H8A···O3^ii	0.97	2.59	3.553 (3)	171
C13—H13···Cl1^iii	0.93	2.82	3.670 (3)	153
C14—H14···O4^i	0.93	2.50	3.211 (4)	134

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+3/2.