1,2-Bis(4-nitro­benzo­yl)-3,4-bis­(4-nitro­phen­yl)cyclo­butane

Xiong, R.-G.

doi:10.1107/S1600536807028954

1,2-Bis(4-nitrobenzoyl)-3,4-bis(4-nitrophenyl)cyclobutane

In the title compound, C₃₀H₂₀N₄O₁₀, a typical bonding pattern is observed for the cyclobutane ring, with an average bond length of 1.560 (3) Å and bond angles of around 90°. In the crystal structure, the relatively short distances between the centroids of the benzene rings of neighbouring molecules [3.865 (3) and 3.845 (3) Å] indicate the existence of π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028954/cv2260sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028954/cv2260Isup2.hkl Contains datablock I

CCDC reference: 654999

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Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R factor = 0.055
wR factor = 0.134
Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C4     = ...          S

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

Comment top

Since the work of Schmidt which delineated a 'topochemical principle' for [2 + 2] photoreactions in the solid state(Schmidt, 1971) chemists have strived to design molecules that will predictably crystallize to allow such reactions to occur (MacGillivray et al., 2000; Toh et al., 2005; Papaefstathiou et al., 2001). Such an approach to the synthesis can lead to the formation of covalent bonds 'at will' in solids to facilitate the high yield, solvent-free synthesis of molecules available either in low yields, as part of mixtures, or are not accessible in the liquid phase. Herein we present the crystal structure of the title compound, (I), accidentally synthesized through photochemical [2 + 2] cycloaddition.

The crystal data shows that in the title compound, C₃₀H₂₀N₄O₁₀, there is a rigid four-membered rings A (C1—C4), The C—C bond lendths of C1—C2, C2—C3, C3—C4 and C1—C4 are 1.587 (3), 1.534 (3), 1.567 (3) and 1.553 (3) Å, respectively. It's average bond lendths is 1.560 (3) Å which is longer than the typical C_sp3—C_sp3 bond distance and is almost same observed in 1,2-dibenzoyl-3,4-bis(4-methoxyphenyl)cyclobutane (Steyl et al., 2005), where the average C—C bond length is 1.563 (3) Å. Such an elongation has also been observed in another rigid four-membered rings derivative (Toda et al., 1998) and is considered to be caused by the tensile force of rigid four-membered rings. The relatively short distances Cg1···Cg1ⁱ of 3.865 (3) Å and Cg2···Cg3ⁱⁱ of 3.845 (3) Å [Cg1, Cg2 and Cg3 are centroids of C18—C23, C11—C16 and C25—C30 rings, respectively] show an existence of weak π···π interactions, which contribute to the crystal packing stabilization [symmetry codes: (i) 1 - x, -y, -z; (ii) x, 1/2 - y, -1/2 + z].

Related literature top

For background and details of the `topochemical principle' for [2 + 2] photoreactions in the solid state, see: Schmidt (1971); MacGillivray et al. (2000); Toh et al. (2005); Papaefstathiou et al. (2001). For crystal structures of related compounds, see: Steyl et al. (2005) and Toda et al. (1998).

Experimental top

1,3-Bis(4-nitrophenyl)prop-2-en-1-one (0.298 g, 2 mmol) was dissolved in ethanol (25 ml) and evaporated slowly in the air affording yellow block crystals of complex I under sunlight.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecule structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

1,2-Bis(4-nitrobenzoyl)-3,4-bis(4-nitrophenyl)cyclobutane top

Crystal data top

C₃₀H₂₀N₄O₁₀	F(000) = 1232
M_r = 596.50	D_x = 1.460 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5718 reflections
a = 17.1005 (11) Å	θ = 2.1–26.1°
b = 10.6509 (6) Å	µ = 0.11 mm⁻¹
c = 15.0484 (9) Å	T = 291 K
β = 98.1630 (11)°	Block, yellow
V = 2713.1 (3) Å³	0.30 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	5326 independent reflections
Radiation source: sealed tube	3493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −21→12
T_min = 0.97, T_max = 0.97	k = −13→13
14024 measured reflections	l = −18→18

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0648P)² + 0.0937P] where P = (F_o² + 2F_c²)/3
5326 reflections	(Δ/σ)_max < 0.001
397 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₃₀H₂₀N₄O₁₀	V = 2713.1 (3) Å³
M_r = 596.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.1005 (11) Å	µ = 0.11 mm⁻¹
b = 10.6509 (6) Å	T = 291 K
c = 15.0484 (9) Å	0.30 × 0.26 × 0.24 mm
β = 98.1630 (11)°

Data collection top

Bruker SMART APEX CCD diffractometer	5326 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3493 reflections with I > 2σ(I)
T_min = 0.97, T_max = 0.97	R_int = 0.034
14024 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
5326 reflections	Δρ_min = −0.20 e Å⁻³
397 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.24207 (14)	0.1731 (2)	0.27043 (15)	0.0513 (6)
H1	0.2486	0.1938	0.3345	0.062*
C2	0.27985 (14)	0.2795 (2)	0.21614 (15)	0.0478 (5)
H2	0.3139	0.3318	0.2590	0.057*
C3	0.33138 (13)	0.1800 (2)	0.17889 (15)	0.0465 (5)
H3	0.3064	0.1544	0.1190	0.056*
C4	0.30906 (14)	0.0838 (2)	0.25000 (15)	0.0465 (5)
H4	0.2886	0.0048	0.2225	0.056*
C5	0.15684 (14)	0.1418 (2)	0.23690 (16)	0.0516 (6)
C6	0.13487 (16)	0.0522 (3)	0.17200 (18)	0.0612 (7)
H6	0.1731	0.0035	0.1502	0.073*
C7	0.05493 (16)	0.0347 (3)	0.13901 (19)	0.0630 (7)
H7	0.0396	−0.0255	0.0953	0.076*
C8	0.00024 (13)	0.1065 (2)	0.17144 (16)	0.0487 (5)
C9	0.02065 (15)	0.1967 (2)	0.23477 (17)	0.0564 (6)
H9	−0.0180	0.2466	0.2546	0.068*
C10	0.09907 (15)	0.2134 (2)	0.26906 (18)	0.0578 (6)
H10	0.1133	0.2726	0.3138	0.069*
C11	0.22659 (14)	0.3643 (2)	0.15479 (17)	0.0510 (6)
C12	0.20188 (15)	0.4766 (2)	0.18928 (17)	0.0549 (6)
H12	0.2202	0.4981	0.2485	0.066*
C13	0.15098 (16)	0.5565 (2)	0.13770 (18)	0.0593 (7)
H13	0.1350	0.6313	0.1614	0.071*
C14	0.12455 (16)	0.5239 (3)	0.05148 (19)	0.0615 (7)
C15	0.14666 (15)	0.4132 (2)	0.01427 (18)	0.0588 (6)
H15	0.1271	0.3922	−0.0447	0.071*
C16	0.19831 (16)	0.3346 (2)	0.06639 (17)	0.0601 (7)
H16	0.2144	0.2605	0.0418	0.072*
C17	0.41546 (15)	0.2195 (2)	0.17426 (15)	0.0497 (5)
C18	0.47535 (14)	0.1283 (2)	0.15019 (15)	0.0466 (5)
C19	0.54917 (15)	0.1712 (3)	0.14035 (18)	0.0584 (6)
H19	0.5615	0.2554	0.1513	0.070*
C20	0.60527 (15)	0.0923 (2)	0.11459 (17)	0.0560 (6)
H20	0.6556	0.1220	0.1098	0.067*
C21	0.58645 (14)	−0.0291 (2)	0.09623 (15)	0.0493 (6)
C22	0.51468 (15)	−0.0784 (2)	0.10701 (16)	0.0535 (6)
H22	0.5037	−0.1631	0.0964	0.064*
C23	0.45837 (14)	0.0018 (2)	0.13435 (16)	0.0515 (6)
H23	0.4090	−0.0295	0.1421	0.062*
C24	0.36941 (14)	0.0631 (2)	0.33040 (15)	0.0453 (5)
C25	0.34748 (13)	−0.0183 (2)	0.40435 (15)	0.0451 (5)
C26	0.39091 (14)	−0.0081 (2)	0.48922 (16)	0.0523 (6)
H26	0.4313	0.0509	0.4992	0.063*
C27	0.37552 (16)	−0.0831 (2)	0.55852 (18)	0.0587 (6)
H27	0.4052	−0.0766	0.6151	0.070*
C28	0.31505 (15)	−0.1683 (2)	0.54202 (17)	0.0539 (6)
C29	0.27006 (15)	−0.1799 (2)	0.46023 (17)	0.0552 (6)
H29	0.2297	−0.2391	0.4510	0.066*
C30	0.28551 (14)	−0.1019 (2)	0.39095 (17)	0.0529 (6)
H30	0.2539	−0.1061	0.3354	0.063*
N1	−0.08286 (14)	0.0903 (2)	0.13593 (15)	0.0591 (5)
N2	0.07123 (13)	0.6107 (2)	−0.00524 (16)	0.0608 (6)
N3	0.64516 (13)	−0.1109 (2)	0.06240 (13)	0.0562 (5)
N4	0.30011 (13)	−0.2532 (2)	0.61511 (15)	0.0561 (5)
O1	−0.13121 (11)	0.16035 (19)	0.16093 (12)	0.0681 (5)
O2	−0.10009 (11)	0.00350 (18)	0.08137 (13)	0.0669 (5)
O3	0.04865 (12)	0.57942 (18)	−0.08239 (15)	0.0708 (5)
O4	0.05367 (11)	0.70834 (19)	0.02810 (13)	0.0674 (5)
O5	0.71007 (11)	−0.06971 (17)	0.06117 (12)	0.0618 (5)
O6	0.62652 (10)	−0.21424 (16)	0.03760 (11)	0.0532 (4)
O7	0.43348 (10)	0.32942 (16)	0.18512 (12)	0.0588 (4)
O8	0.33738 (11)	−0.24460 (17)	0.68674 (12)	0.0636 (5)
O9	0.25094 (11)	−0.33148 (18)	0.59804 (12)	0.0681 (5)
O10	0.43402 (10)	0.11166 (17)	0.33775 (12)	0.0590 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0532 (14)	0.0555 (14)	0.0430 (12)	0.0094 (11)	−0.0011 (10)	−0.0029 (10)
C2	0.0485 (13)	0.0510 (13)	0.0429 (11)	0.0063 (10)	0.0031 (10)	−0.0036 (10)
C3	0.0492 (12)	0.0489 (13)	0.0397 (11)	0.0089 (10)	0.0003 (9)	−0.0022 (9)
C4	0.0480 (13)	0.0484 (13)	0.0437 (12)	0.0042 (10)	0.0086 (10)	−0.0044 (10)
C5	0.0528 (14)	0.0532 (14)	0.0492 (13)	0.0076 (11)	0.0080 (11)	0.0114 (11)
C6	0.0532 (15)	0.0659 (16)	0.0620 (15)	0.0087 (12)	−0.0003 (12)	−0.0079 (13)
C7	0.0588 (16)	0.0633 (16)	0.0618 (15)	0.0047 (13)	−0.0088 (13)	−0.0081 (13)
C8	0.0433 (12)	0.0533 (13)	0.0515 (13)	−0.0105 (11)	0.0140 (10)	0.0147 (11)
C9	0.0597 (15)	0.0497 (14)	0.0598 (15)	0.0166 (12)	0.0081 (12)	0.0136 (12)
C10	0.0609 (15)	0.0561 (15)	0.0599 (14)	0.0143 (12)	0.0203 (12)	0.0095 (12)
C11	0.0510 (13)	0.0500 (13)	0.0541 (13)	0.0116 (11)	0.0147 (11)	0.0058 (11)
C12	0.0545 (14)	0.0590 (15)	0.0528 (14)	0.0183 (12)	0.0132 (11)	0.0002 (11)
C13	0.0663 (16)	0.0515 (14)	0.0651 (16)	0.0170 (12)	0.0266 (13)	0.0165 (12)
C14	0.0620 (16)	0.0591 (16)	0.0653 (16)	0.0108 (12)	0.0157 (13)	0.0305 (13)
C15	0.0600 (16)	0.0597 (16)	0.0541 (14)	0.0070 (12)	−0.0007 (12)	0.0139 (12)
C16	0.0673 (16)	0.0534 (14)	0.0576 (15)	0.0265 (12)	0.0015 (12)	0.0058 (12)
C17	0.0582 (14)	0.0444 (13)	0.0459 (12)	0.0028 (11)	0.0053 (10)	0.0024 (10)
C18	0.0480 (12)	0.0505 (13)	0.0407 (11)	0.0028 (10)	0.0041 (9)	0.0051 (10)
C19	0.0562 (15)	0.0601 (15)	0.0586 (14)	−0.0125 (12)	0.0074 (12)	−0.0097 (12)
C20	0.0557 (15)	0.0589 (16)	0.0564 (14)	−0.0107 (12)	0.0184 (12)	−0.0023 (12)
C21	0.0466 (13)	0.0590 (15)	0.0420 (12)	0.0068 (11)	0.0052 (10)	0.0048 (10)
C22	0.0615 (15)	0.0461 (13)	0.0534 (14)	0.0022 (11)	0.0097 (11)	0.0044 (11)
C23	0.0477 (13)	0.0531 (14)	0.0559 (14)	0.0010 (11)	0.0142 (11)	0.0080 (11)
C24	0.0455 (13)	0.0430 (12)	0.0478 (12)	0.0076 (10)	0.0077 (10)	−0.0049 (10)
C25	0.0466 (12)	0.0420 (12)	0.0460 (12)	0.0087 (10)	0.0039 (10)	−0.0006 (9)
C26	0.0492 (13)	0.0545 (14)	0.0501 (13)	−0.0020 (11)	−0.0031 (10)	0.0060 (11)
C27	0.0560 (15)	0.0634 (16)	0.0532 (14)	0.0083 (13)	−0.0045 (11)	0.0092 (12)
C28	0.0593 (15)	0.0425 (13)	0.0602 (15)	0.0093 (11)	0.0090 (12)	0.0130 (11)
C29	0.0551 (14)	0.0508 (14)	0.0586 (14)	−0.0033 (11)	0.0047 (11)	0.0039 (11)
C30	0.0450 (13)	0.0599 (15)	0.0524 (13)	−0.0018 (11)	0.0026 (10)	−0.0015 (11)
N1	0.0540 (12)	0.0598 (13)	0.0608 (13)	0.0059 (11)	−0.0017 (10)	0.0126 (11)
N2	0.0618 (13)	0.0553 (13)	0.0653 (14)	0.0142 (11)	0.0088 (11)	0.0298 (11)
N3	0.0546 (13)	0.0653 (15)	0.0479 (11)	0.0064 (11)	0.0049 (9)	0.0010 (10)
N4	0.0564 (13)	0.0480 (12)	0.0615 (13)	−0.0013 (10)	0.0005 (11)	0.0181 (9)
O1	0.0551 (11)	0.0851 (14)	0.0651 (11)	0.0209 (10)	0.0122 (9)	0.0273 (10)
O2	0.0621 (11)	0.0652 (12)	0.0650 (11)	−0.0193 (9)	−0.0194 (9)	0.0111 (10)
O3	0.0671 (12)	0.0650 (12)	0.0735 (13)	0.0146 (9)	−0.0133 (10)	0.0153 (10)
O4	0.0670 (12)	0.0633 (12)	0.0662 (11)	0.0141 (10)	−0.0104 (9)	0.0162 (10)
O5	0.0615 (12)	0.0660 (11)	0.0625 (11)	0.0013 (9)	0.0247 (9)	−0.0231 (9)
O6	0.0545 (10)	0.0524 (10)	0.0579 (10)	0.0135 (8)	0.0260 (8)	−0.0019 (8)
O7	0.0618 (10)	0.0510 (10)	0.0661 (11)	−0.0042 (8)	0.0177 (9)	−0.0080 (8)
O8	0.0646 (11)	0.0615 (11)	0.0602 (11)	−0.0165 (9)	−0.0063 (9)	0.0229 (8)
O9	0.0729 (12)	0.0657 (11)	0.0595 (10)	−0.0248 (10)	−0.0116 (9)	0.0278 (9)
O10	0.0528 (10)	0.0618 (11)	0.0622 (11)	−0.0123 (9)	0.0076 (8)	0.0047 (8)

Geometric parameters (Å, º) top

C1—C5	1.510 (3)	C17—O7	1.215 (3)
C1—C4	1.553 (3)	C17—C18	1.493 (3)
C1—C2	1.587 (3)	C18—C19	1.370 (3)
C1—H1	0.9800	C18—C23	1.392 (3)
C2—C11	1.503 (3)	C19—C20	1.372 (4)
C2—C3	1.534 (3)	C19—H19	0.9300
C2—H2	0.9800	C20—C21	1.352 (3)
C3—C17	1.509 (3)	C20—H20	0.9300
C3—C4	1.567 (3)	C21—C22	1.366 (3)
C3—H3	0.9800	C21—N3	1.474 (3)
C4—C24	1.491 (3)	C22—C23	1.392 (3)
C4—H4	0.9800	C22—H22	0.9300
C5—C6	1.379 (4)	C23—H23	0.9300
C5—C10	1.388 (3)	C24—O10	1.211 (3)
C6—C7	1.399 (4)	C24—C25	1.500 (3)
C6—H6	0.9300	C25—C30	1.377 (3)
C7—C8	1.351 (4)	C25—C26	1.387 (3)
C7—H7	0.9300	C26—C27	1.369 (3)
C8—C9	1.364 (4)	C26—H26	0.9300
C8—N1	1.456 (3)	C27—C28	1.371 (4)
C9—C10	1.378 (4)	C27—H27	0.9300
C9—H9	0.9300	C28—C29	1.361 (4)
C10—H10	0.9300	C28—N4	1.474 (3)
C11—C16	1.386 (4)	C29—C30	1.388 (3)
C11—C12	1.394 (3)	C29—H29	0.9300
C12—C13	1.375 (3)	C30—H30	0.9300
C12—H12	0.9300	N1—O1	1.212 (3)
C13—C14	1.357 (4)	N1—O2	1.244 (3)
C13—H13	0.9300	N2—O4	1.211 (3)
C14—C15	1.381 (4)	N2—O3	1.217 (3)
C14—N2	1.481 (3)	N3—O6	1.191 (3)
C15—C16	1.378 (3)	N3—O5	1.196 (3)
C15—H15	0.9300	N4—O8	1.175 (3)
C16—H16	0.9300	N4—O9	1.186 (3)

C5—C1—C4	120.2 (2)	C15—C16—C11	121.0 (2)
C5—C1—C2	115.44 (18)	C15—C16—H16	119.5
C4—C1—C2	88.26 (17)	C11—C16—H16	119.5
C5—C1—H1	110.4	O7—C17—C18	119.3 (2)
C4—C1—H1	110.4	O7—C17—C3	119.2 (2)
C2—C1—H1	110.4	C18—C17—C3	121.3 (2)
C11—C2—C3	121.33 (19)	C19—C18—C23	118.5 (2)
C11—C2—C1	119.33 (19)	C19—C18—C17	118.9 (2)
C3—C2—C1	89.53 (17)	C23—C18—C17	122.6 (2)
C11—C2—H2	108.3	C18—C19—C20	121.2 (2)
C3—C2—H2	108.3	C18—C19—H19	119.4
C1—C2—H2	108.3	C20—C19—H19	119.4
C17—C3—C2	115.09 (19)	C21—C20—C19	119.2 (2)
C17—C3—C4	122.68 (18)	C21—C20—H20	120.4
C2—C3—C4	89.65 (17)	C19—C20—H20	120.4
C17—C3—H3	109.2	C20—C21—C22	122.4 (2)
C2—C3—H3	109.2	C20—C21—N3	118.8 (2)
C4—C3—H3	109.2	C22—C21—N3	118.8 (2)
C24—C4—C1	112.03 (18)	C21—C22—C23	118.0 (2)
C24—C4—C3	116.30 (19)	C21—C22—H22	121.0
C1—C4—C3	89.60 (17)	C23—C22—H22	121.0
C24—C4—H4	112.3	C18—C23—C22	120.6 (2)
C1—C4—H4	112.3	C18—C23—H23	119.7
C3—C4—H4	112.3	C22—C23—H23	119.7
C6—C5—C10	119.4 (2)	O10—C24—C4	121.9 (2)
C6—C5—C1	122.8 (2)	O10—C24—C25	120.0 (2)
C10—C5—C1	117.6 (2)	C4—C24—C25	118.1 (2)
C5—C6—C7	119.8 (3)	C30—C25—C26	119.0 (2)
C5—C6—H6	120.1	C30—C25—C24	122.2 (2)
C7—C6—H6	120.1	C26—C25—C24	118.7 (2)
C8—C7—C6	119.2 (2)	C27—C26—C25	121.3 (2)
C8—C7—H7	120.4	C27—C26—H26	119.3
C6—C7—H7	120.4	C25—C26—H26	119.3
C7—C8—C9	122.0 (2)	C26—C27—C28	118.0 (2)
C7—C8—N1	119.4 (2)	C26—C27—H27	121.0
C9—C8—N1	118.7 (2)	C28—C27—H27	121.0
C8—C9—C10	119.4 (2)	C29—C28—C27	122.6 (2)
C8—C9—H9	120.3	C29—C28—N4	118.9 (2)
C10—C9—H9	120.3	C27—C28—N4	118.5 (2)
C9—C10—C5	120.1 (3)	C28—C29—C30	118.8 (2)
C9—C10—H10	119.9	C28—C29—H29	120.6
C5—C10—H10	119.9	C30—C29—H29	120.6
C16—C11—C12	118.1 (2)	C25—C30—C29	120.1 (2)
C16—C11—C2	123.4 (2)	C25—C30—H30	119.9
C12—C11—C2	118.5 (2)	C29—C30—H30	119.9
C13—C12—C11	121.5 (3)	O1—N1—O2	123.6 (2)
C13—C12—H12	119.3	O1—N1—C8	119.1 (2)
C11—C12—H12	119.3	O2—N1—C8	117.2 (2)
C14—C13—C12	118.7 (2)	O4—N2—O3	124.5 (2)
C14—C13—H13	120.7	O4—N2—C14	117.8 (2)
C12—C13—H13	120.7	O3—N2—C14	117.7 (2)
C13—C14—C15	122.2 (2)	O6—N3—O5	122.8 (2)
C13—C14—N2	119.1 (3)	O6—N3—C21	119.3 (2)
C15—C14—N2	118.7 (3)	O5—N3—C21	117.9 (2)
C16—C15—C14	118.6 (3)	O8—N4—O9	121.9 (2)
C16—C15—H15	120.7	O8—N4—C28	120.5 (2)
C14—C15—H15	120.7	O9—N4—C28	117.5 (2)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₀N₄O₁₀
M_r	596.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	17.1005 (11), 10.6509 (6), 15.0484 (9)
β (°)	98.1630 (11)
V (Å³)	2713.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.97, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	14024, 5326, 3493
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.134, 1.04
No. of reflections	5326
No. of parameters	397
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

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1,2-Bis(4-nitro­benzo­yl)-3,4-bis­(4-nitro­phen­yl)cyclo­butane

Supporting information

Key indicators

checkCIF/PLATON results

1,2-Bis(4-nitrobenzoyl)-3,4-bis(4-nitrophenyl)cyclobutane