[3-Benzoyl-2,4-bis-(3-nitro-phen-yl)cyclo-but-yl](phen-yl)methanone.

The asymmetric unit of the title compound, C30H22N2O6, comprises a half-mol-ecule of the cyclo-butane derivative. The least-squares planes defined by the respective C atoms of the aromatic substituents inter-sect at angles of 76.81 (7) and 89.22 (8)° with the least-squares plane defined by the C atoms of the cyclo-butane ring. In the crystal, C-H⋯O contacts connect the mol-ecules into a three-dimensional network. The shortest centroid-centroid distance between the two different aromatic rings is 3.9601 (8) Å.

Related literature

For the biological activity of chalcones and cyclo­butane-derived compounds, see: Dimmock et al. (1999 ▶); Marais et al. (2005 ▶); Katerere et al. (2004 ▶); Seidel et al. (2000 ▶). For the crystal structures of similar compounds, see: Zheng et al. (2001 ▶); Zhuang & Zheng (2002 ▶). For general information about the dimerization of chalcones, see: Stobbe & Bremer (1929 ▶); Mustafa (1952 ▶). For puckering analysis of cyclic motifs, see: Cremer & Pople (1975 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C30H22N2O6

M = 506.50

Monoclinic,

a = 5.7850 (1) Å

b = 14.7824 (3) Å

c = 14.3589 (3) Å

β = 104.858 (1)°

V = 1186.86 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.33 × 0.14 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.968, T max = 0.989

11005 measured reflections

2945 independent reflections

2387 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.03

2945 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044650/fj2603sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044650/fj2603Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044650/fj2603Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044650/fj2603Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H22N2O6	F(000) = 528
Mr = 506.50	Dx = 1.417 Mg m−3
Monoclinic, P21/c	Melting point > 523 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7850 (1) Å	Cell parameters from 4849 reflections
b = 14.7824 (3) Å	θ = 2.8–28.3°
c = 14.3589 (3) Å	µ = 0.10 mm−1
β = 104.858 (1)°	T = 200 K
V = 1186.86 (4) Å3	Block, colourless
Z = 2	0.33 × 0.14 × 0.11 mm

Bruker APEXII CCD diffractometer	2945 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 28.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→7
Tmin = 0.968, Tmax = 0.989	k = −17→19
11005 measured reflections	l = −17→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.055P)2 + 0.3935P] where P = (Fo2 + 2Fc2)/3
2945 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.02716 (16)	0.08341 (7)	0.41101 (7)	0.0343 (2)
O2	0.4112 (3)	0.11125 (12)	0.89447 (9)	0.0693 (4)
O3	0.6594 (3)	0.21980 (8)	0.94461 (8)	0.0584 (4)
N1	0.5674 (2)	0.16321 (9)	0.88471 (8)	0.0386 (3)
C1	0.2098 (2)	0.07918 (8)	0.38436 (8)	0.0223 (2)
C2	0.4494 (2)	0.05901 (8)	0.45303 (8)	0.0206 (2)
H2	0.5684	0.1074	0.4506	0.025*
C3	0.44539 (19)	0.03813 (8)	0.55776 (8)	0.0203 (2)
H3	0.2767	0.0331	0.5629	0.024*
C11	0.2032 (2)	0.09061 (8)	0.28021 (8)	0.0224 (2)
C12	0.3971 (2)	0.12395 (9)	0.24994 (9)	0.0266 (3)
H12	0.5414	0.1391	0.2960	0.032*
C13	0.3792 (2)	0.13495 (10)	0.15237 (9)	0.0333 (3)
H13	0.5096	0.1596	0.1318	0.040*
C14	0.1718 (3)	0.11009 (11)	0.08487 (10)	0.0371 (3)
H14	0.1607	0.1173	0.0181	0.045*
C15	−0.0192 (2)	0.07487 (10)	0.11440 (9)	0.0358 (3)
H15	−0.1599	0.0565	0.0680	0.043*
C16	−0.0049 (2)	0.06645 (9)	0.21178 (9)	0.0287 (3)
H16	−0.1381	0.0440	0.2320	0.034*
C21	0.5883 (2)	0.09762 (8)	0.63665 (8)	0.0209 (2)
C22	0.5151 (2)	0.10549 (8)	0.72138 (8)	0.0245 (2)
H22	0.3736	0.0762	0.7275	0.029*
C23	0.6502 (2)	0.15632 (8)	0.79654 (9)	0.0276 (3)
C24	0.8559 (2)	0.20118 (9)	0.79156 (9)	0.0319 (3)
H24	0.9447	0.2362	0.8441	0.038*
C25	0.9279 (2)	0.19330 (9)	0.70728 (10)	0.0307 (3)
H25	1.0684	0.2235	0.7015	0.037*
C26	0.7973 (2)	0.14165 (8)	0.63095 (9)	0.0254 (2)
H26	0.8512	0.1363	0.5740	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0268 (4)	0.0478 (6)	0.0298 (5)	0.0065 (4)	0.0101 (4)	0.0091 (4)
O2	0.0738 (9)	0.1032 (12)	0.0425 (7)	−0.0292 (8)	0.0360 (6)	−0.0212 (7)
O3	0.1001 (10)	0.0466 (7)	0.0285 (5)	−0.0007 (7)	0.0169 (6)	−0.0144 (5)
N1	0.0505 (7)	0.0419 (7)	0.0239 (5)	0.0073 (6)	0.0106 (5)	−0.0050 (5)
C1	0.0250 (5)	0.0196 (5)	0.0222 (5)	0.0009 (4)	0.0059 (4)	0.0023 (4)
C2	0.0227 (5)	0.0199 (5)	0.0194 (5)	−0.0018 (4)	0.0059 (4)	0.0002 (4)
C3	0.0206 (5)	0.0219 (5)	0.0185 (5)	−0.0005 (4)	0.0056 (4)	0.0006 (4)
C11	0.0246 (5)	0.0210 (5)	0.0214 (5)	0.0035 (4)	0.0055 (4)	0.0027 (4)
C12	0.0244 (6)	0.0290 (6)	0.0265 (6)	0.0013 (5)	0.0064 (4)	0.0031 (5)
C13	0.0318 (6)	0.0419 (7)	0.0296 (6)	0.0041 (6)	0.0144 (5)	0.0068 (6)
C14	0.0405 (7)	0.0497 (8)	0.0218 (6)	0.0089 (6)	0.0091 (5)	0.0023 (6)
C15	0.0335 (7)	0.0455 (8)	0.0248 (6)	0.0003 (6)	0.0007 (5)	−0.0029 (6)
C16	0.0258 (6)	0.0320 (6)	0.0276 (6)	−0.0006 (5)	0.0052 (5)	0.0021 (5)
C21	0.0237 (5)	0.0190 (5)	0.0197 (5)	0.0025 (4)	0.0050 (4)	0.0000 (4)
C22	0.0267 (6)	0.0241 (6)	0.0237 (5)	0.0019 (4)	0.0085 (4)	0.0000 (4)
C23	0.0355 (6)	0.0259 (6)	0.0213 (6)	0.0055 (5)	0.0073 (5)	−0.0017 (5)
C24	0.0373 (7)	0.0256 (6)	0.0280 (6)	−0.0008 (5)	−0.0004 (5)	−0.0050 (5)
C25	0.0284 (6)	0.0266 (6)	0.0354 (7)	−0.0052 (5)	0.0050 (5)	−0.0005 (5)
C26	0.0263 (6)	0.0244 (6)	0.0260 (6)	−0.0003 (4)	0.0076 (4)	0.0009 (5)

O1—C1	1.2141 (15)	C13—H13	0.9500
O2—N1	1.2210 (19)	C14—C15	1.383 (2)
O3—N1	1.2199 (16)	C14—H14	0.9500
N1—C23	1.4676 (17)	C15—C16	1.3850 (18)
C1—C11	1.4957 (16)	C15—H15	0.9500
C1—C2	1.5104 (15)	C16—H16	0.9500
C2—C3	1.5412 (15)	C21—C22	1.3917 (16)
C2—C3i	1.5827 (16)	C21—C26	1.3938 (17)
C2—H2	1.0000	C22—C23	1.3810 (17)
C3—C21	1.5032 (15)	C22—H22	0.9500
C3—C2i	1.5827 (16)	C23—C24	1.380 (2)
C3—H3	1.0000	C24—C25	1.382 (2)
C11—C16	1.3910 (16)	C24—H24	0.9500
C11—C12	1.3931 (17)	C25—C26	1.3895 (17)
C12—C13	1.3877 (17)	C25—H25	0.9500
C12—H12	0.9500	C26—H26	0.9500
C13—C14	1.385 (2)
O3—N1—O2	123.53 (13)	C15—C14—C13	120.16 (12)
O3—N1—C23	118.42 (13)	C15—C14—H14	119.9
O2—N1—C23	118.05 (12)	C13—C14—H14	119.9
O1—C1—C11	120.53 (10)	C14—C15—C16	119.85 (12)
O1—C1—C2	122.11 (10)	C14—C15—H15	120.1
C11—C1—C2	117.32 (10)	C16—C15—H15	120.1
C1—C2—C3	115.82 (9)	C15—C16—C11	120.46 (12)
C1—C2—C3i	115.26 (9)	C15—C16—H16	119.8
C3—C2—C3i	90.93 (8)	C11—C16—H16	119.8
C1—C2—H2	111.1	C22—C21—C26	118.37 (10)
C3—C2—H2	111.1	C22—C21—C3	118.42 (10)
C3i—C2—H2	111.1	C26—C21—C3	123.13 (10)
C21—C3—C2	118.37 (9)	C23—C22—C21	119.39 (12)
C21—C3—C2i	116.97 (9)	C23—C22—H22	120.3
C2—C3—C2i	89.07 (8)	C21—C22—H22	120.3
C21—C3—H3	110.3	C24—C23—C22	122.92 (12)
C2—C3—H3	110.3	C24—C23—N1	119.20 (11)
C2i—C3—H3	110.3	C22—C23—N1	117.87 (12)
C16—C11—C12	119.38 (11)	C23—C24—C25	117.54 (11)
C16—C11—C1	118.23 (11)	C23—C24—H24	121.2
C12—C11—C1	122.39 (10)	C25—C24—H24	121.2
C13—C12—C11	119.94 (11)	C24—C25—C26	120.79 (12)
C13—C12—H12	120.0	C24—C25—H25	119.6
C11—C12—H12	120.0	C26—C25—H25	119.6
C14—C13—C12	120.16 (12)	C25—C26—C21	120.99 (11)
C14—C13—H13	119.9	C25—C26—H26	119.5
C12—C13—H13	119.9	C21—C26—H26	119.5
O1—C1—C2—C3	3.75 (16)	C1—C11—C16—C15	−179.34 (12)
C11—C1—C2—C3	−174.02 (9)	C2—C3—C21—C22	153.77 (10)
O1—C1—C2—C3i	108.12 (13)	C2i—C3—C21—C22	−101.51 (12)
C11—C1—C2—C3i	−69.65 (13)	C2—C3—C21—C26	−29.57 (16)
C1—C2—C3—C21	−120.73 (11)	C2i—C3—C21—C26	75.16 (14)
C3i—C2—C3—C21	120.45 (11)	C26—C21—C22—C23	0.10 (17)
C1—C2—C3—C2i	118.82 (11)	C3—C21—C22—C23	176.93 (11)
C3i—C2—C3—C2i	0.0	C21—C22—C23—C24	0.70 (19)
O1—C1—C11—C16	−28.05 (17)	C21—C22—C23—N1	179.91 (11)
C2—C1—C11—C16	149.76 (11)	O3—N1—C23—C24	11.86 (19)
O1—C1—C11—C12	152.23 (12)	O2—N1—C23—C24	−167.48 (14)
C2—C1—C11—C12	−29.96 (16)	O3—N1—C23—C22	−167.39 (13)
C16—C11—C12—C13	1.65 (18)	O2—N1—C23—C22	13.3 (2)
C1—C11—C12—C13	−178.63 (12)	C22—C23—C24—C25	−0.62 (19)
C11—C12—C13—C14	−2.1 (2)	N1—C23—C24—C25	−179.82 (12)
C12—C13—C14—C15	0.5 (2)	C23—C24—C25—C26	−0.24 (19)
C13—C14—C15—C16	1.5 (2)	C24—C25—C26—C21	1.03 (19)
C14—C15—C16—C11	−2.0 (2)	C22—C21—C26—C25	−0.94 (18)
C12—C11—C16—C15	0.39 (19)	C3—C21—C26—C25	−177.61 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	1.00	2.40	2.8509 (14)	106
C3—H3···O1ii	1.00	2.56	3.3957 (15)	141
C14—H14···O2iii	0.95	2.56	3.3666 (19)	142
C2—H2···O3iv	1.00	2.61	3.5009 (17)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	1.00	2.56	3.3957 (15)	141
C14—H14⋯O2ii	0.95	2.56	3.3666 (19)	142
C2—H2⋯O3iii	1.00	2.61	3.5009 (17)	148

Symmetry codes: (i) ; (ii) ; (iii) .