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

Sheshadri, S.N.; Chidan Kumar, C.S.; Naveen, S.; Veeraiah, M.K.; Raghava Reddy, K.; Warad, I.

doi:10.1107/S2056989019013975

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

S. N. Sheshadri, C. S. Chidan Kumar, S. Naveen, M. K. Veeraiah, K. Raghava Reddy and I. Warad

The title compound, 2-(4-nitrophenyl)-2-oxoethyl benzoate, is relatively planar with the two aromatic rings being inclined to each other by 3.09 (5)°.

Keywords: crystal structure; $R_{2}^{2}$ (16) ring motif; C-H

O hydrogen bonds; offset π–π interactions; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019013975/su5520sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019013975/su5520Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019013975/su5520Isup5.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019013975/su5520sup3.pdf CSD search file S1
	Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019013975/su5520sup4.pdf CSD search file S2

CCDC reference: 1449646

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C)= 0.002 Å
R factor = 0.041
wR factor = 0.120
Data-to-parameter ratio = 19.5

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

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 benzoate top

Crystal data top

C₁₅H₁₁NO₅	F(000) = 592
M_r = 285.25	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3133 reflections
a = 7.3371 (4) Å	θ = 1.9–30.2°
b = 21.0051 (11) Å	µ = 0.12 mm⁻¹
c = 8.3069 (4) Å	T = 100 K
β = 102.711 (1)°	Needle, colourless
V = 1248.86 (11) Å³	0.37 × 0.19 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3496 independent reflections
Radiation source: Rotating Anode	3133 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 18.4 pixels mm^-1	θ_max = 30.2°, θ_min = 1.9°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −29→29
T_min = 0.959, T_max = 0.988	l = −11→11
14140 measured reflections

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0687P)² + 0.3119P] where P = (F_o² + 2F_c²)/3
3696 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.14827 (11)	0.38115 (4)	0.37625 (9)	0.0160 (2)
O2	0.34743 (16)	0.30646 (4)	0.58368 (11)	0.0357 (3)
O3	−0.02999 (13)	0.46698 (4)	0.29186 (10)	0.0227 (3)
O4	0.55675 (12)	0.44140 (4)	1.40112 (10)	0.0228 (2)
O5	0.70482 (14)	0.35199 (5)	1.40652 (11)	0.0292 (3)
N1	0.59732 (13)	0.39281 (5)	1.33492 (11)	0.0167 (2)
C1	0.47223 (14)	0.31711 (5)	0.92088 (13)	0.0142 (3)
C2	0.54458 (14)	0.32506 (5)	1.08833 (13)	0.0142 (3)
C3	0.51595 (14)	0.38305 (5)	1.15843 (12)	0.0129 (2)
C4	0.41568 (14)	0.43237 (5)	1.06970 (13)	0.0137 (2)
C5	0.34479 (14)	0.42390 (5)	0.90160 (12)	0.0128 (2)
C6	0.37472 (13)	0.36653 (5)	0.82655 (12)	0.0123 (2)
C7	0.30848 (15)	0.35532 (5)	0.64525 (13)	0.0152 (3)
C8	0.19380 (15)	0.40611 (5)	0.54070 (12)	0.0144 (3)
C9	0.03139 (14)	0.41587 (5)	0.26299 (12)	0.0132 (2)
C10	−0.01390 (13)	0.38341 (5)	0.09985 (12)	0.0122 (2)
C11	−0.11222 (14)	0.41756 (5)	−0.03566 (13)	0.0140 (3)
C12	−0.16055 (14)	0.38880 (5)	−0.18959 (13)	0.0159 (3)
C13	−0.11199 (15)	0.32571 (5)	−0.20797 (13)	0.0168 (3)
C14	−0.01248 (15)	0.29164 (5)	−0.07323 (13)	0.0162 (3)
C15	0.03811 (14)	0.32043 (5)	0.08058 (13)	0.0138 (3)
H1	0.48900	0.27770	0.86970	0.0170*
H2	0.61170	0.29180	1.15300	0.0170*
H4	0.39580	0.47110	1.12250	0.0160*
H5	0.27610	0.45710	0.83790	0.0150*
H8A	0.07880	0.41510	0.58050	0.0170*
H8B	0.26650	0.44600	0.54450	0.0170*
H11	−0.14620	0.46060	−0.02260	0.0170*
H12	−0.22660	0.41220	−0.28210	0.0190*
H13	−0.14680	0.30570	−0.31290	0.0200*
H14	0.02090	0.24860	−0.08660	0.0190*
H15	0.10770	0.29740	0.17220	0.0170*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0200 (4)	0.0170 (4)	0.0090 (3)	0.0052 (3)	−0.0008 (3)	−0.0008 (3)
O2	0.0581 (7)	0.0226 (4)	0.0179 (4)	0.0205 (4)	−0.0097 (4)	−0.0078 (3)
O3	0.0325 (5)	0.0174 (4)	0.0160 (4)	0.0090 (3)	0.0003 (3)	−0.0014 (3)
O4	0.0256 (4)	0.0266 (4)	0.0150 (4)	0.0018 (3)	0.0018 (3)	−0.0064 (3)
O5	0.0366 (5)	0.0313 (5)	0.0149 (4)	0.0113 (4)	−0.0048 (4)	0.0036 (3)
N1	0.0159 (4)	0.0219 (4)	0.0115 (4)	0.0000 (3)	0.0015 (3)	0.0007 (3)
C1	0.0155 (5)	0.0123 (4)	0.0142 (5)	−0.0001 (3)	0.0017 (4)	0.0004 (3)
C2	0.0142 (5)	0.0138 (4)	0.0137 (5)	0.0008 (3)	0.0012 (4)	0.0032 (3)
C3	0.0120 (4)	0.0171 (4)	0.0093 (4)	−0.0018 (3)	0.0015 (3)	0.0007 (3)
C4	0.0142 (4)	0.0138 (4)	0.0128 (4)	0.0007 (3)	0.0026 (4)	−0.0012 (3)
C5	0.0130 (4)	0.0128 (4)	0.0119 (4)	0.0016 (3)	0.0010 (3)	0.0007 (3)
C6	0.0117 (4)	0.0126 (4)	0.0119 (4)	−0.0012 (3)	0.0012 (3)	−0.0005 (3)
C7	0.0171 (5)	0.0145 (4)	0.0120 (4)	0.0007 (4)	−0.0012 (4)	−0.0007 (3)
C8	0.0184 (5)	0.0149 (4)	0.0089 (4)	0.0024 (4)	0.0010 (4)	−0.0004 (3)
C9	0.0139 (4)	0.0142 (4)	0.0112 (4)	−0.0001 (3)	0.0020 (4)	0.0019 (3)
C10	0.0115 (4)	0.0144 (4)	0.0106 (4)	−0.0010 (3)	0.0021 (3)	0.0002 (3)
C11	0.0136 (4)	0.0151 (4)	0.0129 (5)	0.0012 (3)	0.0022 (4)	0.0021 (3)
C12	0.0142 (5)	0.0207 (5)	0.0118 (5)	−0.0004 (4)	0.0007 (4)	0.0030 (4)
C13	0.0180 (5)	0.0209 (5)	0.0109 (4)	−0.0024 (4)	0.0022 (4)	−0.0011 (4)
C14	0.0203 (5)	0.0156 (5)	0.0128 (5)	0.0002 (4)	0.0041 (4)	−0.0012 (4)
C15	0.0157 (5)	0.0142 (4)	0.0113 (4)	0.0004 (3)	0.0027 (4)	0.0015 (3)

Geometric parameters (Å, º) top

O1—C8	1.4324 (12)	C10—C15	1.3958 (15)
O1—C9	1.3407 (13)	C11—C12	1.3879 (15)
O2—C7	1.2087 (14)	C12—C13	1.3894 (15)
O3—C9	1.2085 (14)	C13—C14	1.3923 (15)
O4—N1	1.2267 (13)	C14—C15	1.3883 (15)
O5—N1	1.2266 (14)	C1—H1	0.9500
N1—C3	1.4706 (13)	C2—H2	0.9500
C1—C2	1.3855 (15)	C4—H4	0.9500
C1—C6	1.3988 (15)	C5—H5	0.9500
C2—C3	1.3859 (15)	C8—H8A	0.9900
C3—C4	1.3853 (15)	C8—H8B	0.9900
C4—C5	1.3901 (14)	C11—H11	0.9500
C5—C6	1.3962 (15)	C12—H12	0.9500
C6—C7	1.4959 (14)	C13—H13	0.9500
C7—C8	1.5096 (15)	C14—H14	0.9500
C9—C10	1.4878 (14)	C15—H15	0.9500
C10—C11	1.3945 (14)

C8—O1—C9	116.69 (8)	C12—C13—C14	120.25 (10)
O4—N1—O5	123.90 (9)	C13—C14—C15	120.18 (10)
O4—N1—C3	118.53 (9)	C10—C15—C14	119.60 (10)
O5—N1—C3	117.56 (9)	C2—C1—H1	120.00
C2—C1—C6	120.58 (10)	C6—C1—H1	120.00
C1—C2—C3	117.89 (10)	C1—C2—H2	121.00
N1—C3—C2	118.40 (9)	C3—C2—H2	121.00
N1—C3—C4	118.54 (9)	C3—C4—H4	121.00
C2—C3—C4	123.06 (9)	C5—C4—H4	121.00
C3—C4—C5	118.44 (10)	C4—C5—H5	120.00
C4—C5—C6	119.88 (9)	C6—C5—H5	120.00
C1—C6—C5	120.11 (9)	O1—C8—H8A	111.00
C1—C6—C7	117.39 (9)	O1—C8—H8B	111.00
C5—C6—C7	122.50 (9)	C7—C8—H8A	111.00
O2—C7—C6	120.33 (10)	C7—C8—H8B	111.00
O2—C7—C8	120.69 (10)	H8A—C8—H8B	109.00
C6—C7—C8	118.98 (9)	C10—C11—H11	120.00
O1—C8—C7	105.87 (8)	C12—C11—H11	120.00
O1—C9—O3	123.56 (9)	C11—C12—H12	120.00
O1—C9—C10	111.72 (9)	C13—C12—H12	120.00
O3—C9—C10	124.72 (9)	C12—C13—H13	120.00
C9—C10—C11	118.15 (9)	C14—C13—H13	120.00
C9—C10—C15	121.80 (9)	C13—C14—H14	120.00
C11—C10—C15	120.06 (9)	C15—C14—H14	120.00
C10—C11—C12	120.11 (10)	C10—C15—H15	120.00
C11—C12—C13	119.78 (10)	C14—C15—H15	120.00

C9—O1—C8—C7	174.08 (9)	C1—C6—C7—C8	176.74 (10)
C8—O1—C9—O3	2.69 (15)	C5—C6—C7—O2	175.36 (11)
C8—O1—C9—C10	−176.70 (9)	C5—C6—C7—C8	−4.18 (15)
O4—N1—C3—C2	−172.74 (10)	O2—C7—C8—O1	1.88 (15)
O4—N1—C3—C4	7.80 (15)	C6—C7—C8—O1	−178.58 (9)
O5—N1—C3—C2	8.46 (15)	O1—C9—C10—C11	−171.02 (9)
O5—N1—C3—C4	−171.00 (10)	O1—C9—C10—C15	9.44 (14)
C6—C1—C2—C3	0.43 (16)	O3—C9—C10—C11	9.60 (16)
C2—C1—C6—C5	−1.83 (16)	O3—C9—C10—C15	−169.95 (11)
C2—C1—C6—C7	177.27 (10)	C9—C10—C11—C12	−178.79 (10)
C1—C2—C3—N1	−178.03 (9)	C15—C10—C11—C12	0.77 (15)
C1—C2—C3—C4	1.41 (16)	C9—C10—C15—C14	178.01 (10)
N1—C3—C4—C5	177.65 (9)	C11—C10—C15—C14	−1.52 (15)
C2—C3—C4—C5	−1.79 (16)	C10—C11—C12—C13	0.53 (16)
C3—C4—C5—C6	0.33 (15)	C11—C12—C13—C14	−1.06 (16)
C4—C5—C6—C1	1.43 (15)	C12—C13—C14—C15	0.30 (17)
C4—C5—C6—C7	−177.62 (10)	C13—C14—C15—C10	0.99 (16)
C1—C6—C7—O2	−3.72 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.95	2.47	3.3967 (14)	164
C13—H13···O5ⁱⁱ	0.95	2.54	3.2361 (14)	130

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

π–π contacts (Å, °) in the crystal of the title compound. top

Cg 1 and Cg2 are the centroids of rings C1–C6 and C10–C15, respectively.

Cg(I)	Cg(J)	Cg(I)···Cg(J) (Å)	α (°)	β (°)	γ (°)	CgI_Perp (Å)	CgJ_Perp (Å)	offset (Å)
Cg1	Cg2ⁱⁱⁱ	3.6754 (6)	3.09 (5)	22.5	21.5	3.4199 (4)	3.3948 (4)	1.408
Cg1	Cg2^iv	3.7519 (6)	3.09 (5)	27.9	25.1	3.3975 (4)	3.3171 (4)	1.753
Cg2	Cg1^v	3.7519 (6)	3.09 (5)	25.1	27.9	3.3171 (4)	3.3975 (4)	1.592
Cg2	Cg1^vi	3.6754 (6)	3.09 (5)	21.5	22.5	3.3948 (4)	3.4200 (4)	1.346

Symmetry codes: (iii) x, y, z + 1; (iv) x + 1, y, z + 1; (v) x - 1, y, z - 1; (vi) x, y, z - 1.

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

Supporting information

Key indicators

checkCIF/PLATON results

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