(3aR,7aR)-Bis(4-nitro­phen­yl) 2-oxo­perhydro­benzo[d]imidazole-1,3-di­carboxyl­ate

Xu, Y.-H.; Siegler, M.; Long, S.

doi:10.1107/S1600536807039785

(3aR,7aR)-Bis(4-nitrophenyl) 2-oxoperhydrobenzo[d]imidazole-1,3-dicarboxylate

The title compound, C₂₁H₁₈N₄O₉, is a chiral cyclic urea derivative with an approximate local C₂ axis. The crystal structure is mainly stablized by weak interactions since the molecule does not possess hydrogen-bonding donors. The molecules stack along the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039785/fl2150sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039785/fl2150Isup2.hkl Contains datablock I

CCDC reference: 660306

checkCIF report

Key indicators

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.004 Å
R factor = 0.042
wR factor = 0.103
Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O2     ..  N3      ..       2.83 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O8     ..  C8      ..       2.90 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C14     ..       2.98 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.49
           From the CIF: _reflns_number_total               2724
           Count of symmetry unique reflns         2722
           Completeness (_total/calc)            100.07%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         2
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          R

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), a chiral C2 symmetric cyclic urea derivative, was obtained as a by-product during an attempt to synthesize a linker for the preparation of chiral oligoureas (Long, 2006). Here we report the structure of it.

The asymmetric unit of (I) (Fig. 1) contains one molecule and the bond lengths and angles are within normal ranges (Allen et al., 1987). The chirality of the C atoms (C1 R, C6 R) was assigned based on the known chirality of the starting material, with the assumption that no chirality change took place during the reaction. The cyclohexane ring has a chair conformation and the cyclic C1/C6/N2/C7/N1 urea unit has a twisted envolope conformation with no four atoms in the same plane, similar to the structure of (4R,5R)-4,5-Diphenylimidazolidin-2-one (Siegler and Long, 2006). Since the molecule has no hydrogen bonding donors, the structure is stablized by weak interactions including π stacking. The molecules stack along the a axis, and the distance between the face-to-face π stacking aromatic rings is 6.059 Å. In addition, intramolecular O···O interaction exists as indicated by the distances (O3···O1 = 2.615 Å, and O1···O6 = 2.662 Å) (Fig. 2).

Related literature top

For geometry, see: Allen et al. (1987). For similar structures, see: Long (2006); Siegler & Long (2006).

Experimental top

n-BuLi(8.6 ml, 21.5 mmol) was added dropwise to a round-bottom flask containing tert-butyl (1R,2R)-cyclohexane-1,2-diyldicarbamate (3.14 g, 10 mmol) in 20 ml THF cooled with dry ice. After the resulted solutuion was warmed to ambient temperature, 4-nitrophenyl [1,2-diphenyl-2-(2,2,2-trifluoroacetylamino)ethyl]- carbamate (4.03 g, 20 mmol) in 20 ml THF was added dropwise. The mixture was stirred at room temperature overnight. The solution was washed with 1 N NaOH, water and brine, and then dried with anhydrous Na₂SO₄. After removal of the solvent, the product was recovered as a colorless solid (4.3 g, 91%). Crystals of (I) were obtained by recrystallization from ethyl acetate as colorless blocks.

Structure description top

For geometry, see: Allen et al. (1987). For similar structures, see: Long (2006); Siegler & Long (2006).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and local procedures.

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms).
	Fig. 2. A packing diagram of (I) along a axis.
	Fig. 3. The preparation.

(3aR,7aR)-Bis(4-nitrophenyl) 2-oxoperhydrobenzo[d]imidazole-1,3-dicarboxylate top

Crystal data top

C₂₁H₁₈N₄O₉	D_x = 1.513 Mg m⁻³
M_r = 470.39	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4880 reflections
a = 6.059 (1) Å	θ = 1.0–27.5°
b = 17.956 (3) Å	µ = 0.12 mm⁻¹
c = 18.982 (3) Å	T = 90 K
V = 2065.2 (6) Å³	Block, colourless
Z = 4	0.35 × 0.20 × 0.10 mm
F(000) = 976

Data collection top

Nonius KappaCCD diffractometer	2724 independent reflections
Radiation source: fine-focus sealed tube	2209 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 18 pixels mm^-1	θ_max = 27.5°, θ_min = 1.6°
ω scans at fixed χ = 55°	h = −7→7
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −23→23
T_min = 0.959, T_max = 0.988	l = −24→23
9218 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.067P)²] where P = (F_o² + 2F_c²)/3
2724 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₁H₁₈N₄O₉	V = 2065.2 (6) Å³
M_r = 470.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.059 (1) Å	µ = 0.12 mm⁻¹
b = 17.956 (3) Å	T = 90 K
c = 18.982 (3) Å	0.35 × 0.20 × 0.10 mm

Data collection top

Nonius KappaCCD diffractometer	2724 independent reflections
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	2209 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.988	R_int = 0.049
9218 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
2724 reflections	Δρ_min = −0.31 e Å⁻³
307 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	0.7327 (4)	0.07569 (12)	0.30668 (13)	0.0216 (5)
H1	0.6373	0.0305	0.3025	0.026*
C2	0.9611 (4)	0.05185 (14)	0.32890 (13)	0.0255 (6)
H2A	0.9565	0.0284	0.3761	0.031*
H2B	1.0611	0.0954	0.3309	0.031*
C3	1.0425 (5)	−0.00426 (14)	0.27372 (13)	0.0300 (6)
H3A	0.9539	−0.0504	0.2776	0.036*
H3B	1.1980	−0.0172	0.2841	0.036*
C4	1.0270 (5)	0.02536 (14)	0.19768 (13)	0.0292 (6)
H4A	1.1389	0.0649	0.1911	0.035*
H4B	1.0627	−0.0156	0.1647	0.035*
C5	0.7995 (5)	0.05674 (13)	0.17903 (13)	0.0254 (6)
H5A	0.8026	0.0802	0.1318	0.030*
H5B	0.6877	0.0165	0.1788	0.030*
C6	0.7444 (4)	0.11400 (13)	0.23481 (12)	0.0200 (5)
H6	0.8658	0.1517	0.2362	0.024*
C7	0.4719 (4)	0.17341 (12)	0.30407 (12)	0.0204 (5)
C8	0.4582 (4)	0.19100 (12)	0.17450 (12)	0.0198 (5)
C9	0.1934 (4)	0.27412 (14)	0.12998 (12)	0.0230 (6)
C10	0.3021 (5)	0.33867 (14)	0.10993 (13)	0.0262 (6)
H10	0.4412	0.3513	0.1297	0.031*
C11	0.2022 (5)	0.38445 (13)	0.06004 (13)	0.0260 (6)
H11	0.2729	0.4286	0.0441	0.031*
C12	−0.0020 (5)	0.36406 (13)	0.03427 (12)	0.0225 (6)
C13	−0.1070 (4)	0.29878 (14)	0.05265 (13)	0.0246 (6)
H13	−0.2452	0.2856	0.0326	0.030*
C14	−0.0045 (4)	0.25308 (13)	0.10121 (13)	0.0244 (6)
H14	−0.0709	0.2073	0.1146	0.029*
C15	0.5755 (4)	0.12054 (13)	0.41966 (12)	0.0235 (6)
C16	0.3959 (5)	0.16923 (13)	0.51801 (12)	0.0220 (5)
C17	0.5086 (5)	0.19901 (13)	0.57421 (12)	0.0232 (5)
H17	0.6464	0.2232	0.5677	0.028*
C18	0.4146 (4)	0.19267 (12)	0.64138 (13)	0.0220 (6)
H18	0.4871	0.2124	0.6816	0.026*
C19	0.2146 (4)	0.15713 (13)	0.64735 (12)	0.0205 (5)
C20	0.1017 (4)	0.12713 (12)	0.59117 (13)	0.0220 (5)
H20	−0.0354	0.1024	0.5978	0.026*
C21	0.1940 (5)	0.13401 (13)	0.52468 (13)	0.0239 (6)
H21	0.1199	0.1149	0.4844	0.029*
N1	0.6143 (4)	0.13238 (10)	0.34801 (10)	0.0202 (5)
N2	0.5302 (4)	0.15399 (11)	0.23445 (10)	0.0207 (4)
N3	−0.1138 (4)	0.41454 (12)	−0.01561 (11)	0.0276 (5)
N4	0.1167 (4)	0.14975 (11)	0.71830 (11)	0.0244 (5)
O1	0.3305 (3)	0.21570 (10)	0.32218 (9)	0.0259 (4)
O2	0.5490 (3)	0.18582 (9)	0.11838 (8)	0.0239 (4)
O3	0.2732 (3)	0.23065 (9)	0.18638 (9)	0.0262 (4)
O4	−0.0114 (4)	0.46898 (9)	−0.03702 (10)	0.0365 (5)
O5	−0.3052 (4)	0.40039 (11)	−0.03286 (10)	0.0372 (5)
O6	0.4816 (3)	0.18046 (8)	0.44960 (8)	0.0248 (4)
O7	0.6268 (4)	0.06473 (10)	0.44975 (10)	0.0385 (5)
O8	0.2036 (3)	0.18496 (9)	0.76670 (9)	0.0290 (4)
O9	−0.0414 (3)	0.10836 (10)	0.72600 (9)	0.0327 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0264 (13)	0.0189 (11)	0.0196 (12)	0.0002 (10)	0.0028 (11)	0.0005 (10)
C2	0.0247 (13)	0.0286 (12)	0.0232 (13)	0.0028 (12)	0.0020 (12)	0.0036 (11)
C3	0.0289 (14)	0.0309 (13)	0.0302 (14)	0.0079 (13)	0.0015 (13)	0.0012 (12)
C4	0.0328 (15)	0.0281 (12)	0.0267 (14)	0.0069 (12)	0.0098 (13)	−0.0013 (11)
C5	0.0312 (14)	0.0237 (12)	0.0213 (13)	0.0017 (12)	0.0022 (12)	−0.0008 (11)
C6	0.0225 (13)	0.0208 (12)	0.0167 (11)	0.0003 (10)	0.0015 (11)	0.0028 (10)
C7	0.0218 (12)	0.0212 (11)	0.0183 (12)	0.0010 (11)	0.0024 (11)	−0.0004 (10)
C8	0.0220 (12)	0.0202 (11)	0.0173 (12)	−0.0008 (10)	−0.0036 (11)	0.0013 (9)
C9	0.0272 (14)	0.0286 (13)	0.0132 (11)	0.0076 (12)	0.0014 (11)	0.0022 (10)
C10	0.0274 (14)	0.0300 (13)	0.0211 (12)	0.0010 (12)	−0.0020 (12)	−0.0019 (11)
C11	0.0338 (15)	0.0237 (12)	0.0204 (12)	−0.0005 (12)	0.0016 (12)	−0.0032 (11)
C12	0.0315 (15)	0.0227 (11)	0.0132 (11)	0.0066 (12)	0.0018 (11)	0.0006 (9)
C13	0.0225 (13)	0.0324 (13)	0.0189 (12)	0.0001 (11)	−0.0017 (12)	0.0012 (11)
C14	0.0259 (13)	0.0265 (12)	0.0207 (12)	−0.0002 (11)	0.0053 (12)	0.0022 (10)
C15	0.0292 (14)	0.0240 (12)	0.0174 (11)	0.0015 (11)	0.0019 (11)	0.0031 (10)
C16	0.0313 (14)	0.0209 (11)	0.0138 (11)	0.0038 (11)	0.0025 (11)	0.0000 (10)
C17	0.0267 (14)	0.0223 (11)	0.0207 (12)	−0.0006 (11)	0.0015 (11)	0.0012 (10)
C18	0.0281 (14)	0.0221 (12)	0.0158 (11)	−0.0017 (11)	−0.0015 (11)	0.0010 (10)
C19	0.0263 (14)	0.0211 (11)	0.0141 (11)	0.0023 (11)	0.0010 (11)	0.0000 (9)
C20	0.0211 (12)	0.0220 (11)	0.0230 (12)	−0.0008 (11)	−0.0004 (11)	−0.0001 (10)
C21	0.0328 (15)	0.0203 (12)	0.0186 (12)	0.0010 (12)	−0.0050 (12)	−0.0017 (10)
N1	0.0258 (11)	0.0205 (9)	0.0144 (9)	0.0053 (9)	0.0028 (9)	0.0011 (8)
N2	0.0239 (11)	0.0239 (10)	0.0143 (10)	0.0040 (9)	0.0008 (9)	0.0020 (8)
N3	0.0346 (14)	0.0267 (11)	0.0214 (11)	0.0053 (11)	−0.0009 (11)	−0.0009 (9)
N4	0.0297 (12)	0.0228 (10)	0.0206 (11)	0.0008 (10)	0.0022 (10)	0.0004 (9)
O1	0.0294 (10)	0.0306 (9)	0.0175 (9)	0.0074 (9)	0.0019 (8)	0.0022 (8)
O2	0.0292 (10)	0.0268 (9)	0.0156 (8)	0.0015 (8)	0.0025 (8)	−0.0010 (7)
O3	0.0251 (9)	0.0360 (9)	0.0174 (8)	0.0087 (8)	0.0012 (8)	0.0082 (8)
O4	0.0520 (14)	0.0241 (9)	0.0333 (11)	−0.0013 (10)	−0.0014 (11)	0.0062 (8)
O5	0.0337 (12)	0.0447 (12)	0.0332 (11)	0.0078 (10)	−0.0082 (10)	0.0078 (9)
O6	0.0363 (11)	0.0229 (8)	0.0150 (8)	0.0035 (8)	0.0055 (8)	0.0013 (7)
O7	0.0573 (14)	0.0358 (10)	0.0223 (9)	0.0176 (10)	0.0088 (10)	0.0091 (9)
O8	0.0342 (10)	0.0347 (10)	0.0180 (9)	−0.0028 (9)	0.0027 (9)	−0.0059 (8)
O9	0.0354 (11)	0.0338 (10)	0.0290 (10)	−0.0123 (9)	0.0093 (10)	−0.0017 (8)

Geometric parameters (Å, º) top

C1—N1	1.472 (3)	C10—H10	0.9500
C1—C2	1.509 (4)	C11—C12	1.380 (4)
C1—C6	1.530 (3)	C11—H11	0.9500
C1—H1	1.0000	C12—C13	1.378 (3)
C2—C3	1.535 (3)	C12—N3	1.476 (3)
C2—H2A	0.9900	C13—C14	1.381 (3)
C2—H2B	0.9900	C13—H13	0.9500
C3—C4	1.541 (3)	C14—H14	0.9500
C3—H3A	0.9900	C15—O7	1.194 (3)
C3—H3B	0.9900	C15—O6	1.343 (3)
C4—C5	1.531 (4)	C15—N1	1.397 (3)
C4—H4A	0.9900	C16—C17	1.375 (4)
C4—H4B	0.9900	C16—C21	1.383 (4)
C5—C6	1.513 (3)	C16—O6	1.413 (3)
C5—H5A	0.9900	C17—C18	1.401 (3)
C5—H5B	0.9900	C17—H17	0.9500
C6—N2	1.484 (3)	C18—C19	1.374 (4)
C6—H6	1.0000	C18—H18	0.9500
C7—O1	1.195 (3)	C19—C20	1.377 (3)
C7—N1	1.408 (3)	C19—N4	1.477 (3)
C7—N2	1.412 (3)	C20—C21	1.386 (3)
C8—O2	1.202 (3)	C20—H20	0.9500
C8—O3	1.347 (3)	C21—H21	0.9500
C8—N2	1.388 (3)	N3—O4	1.227 (3)
C9—C14	1.371 (4)	N3—O5	1.232 (3)
C9—C10	1.386 (4)	N4—O9	1.222 (3)
C9—O3	1.410 (3)	N4—O8	1.233 (3)
C10—C11	1.393 (4)

N1—C1—C2	119.6 (2)	C12—C11—C10	118.3 (2)
N1—C1—C6	100.78 (17)	C12—C11—H11	120.9
C2—C1—C6	109.5 (2)	C10—C11—H11	120.9
N1—C1—H1	108.8	C13—C12—C11	123.3 (2)
C2—C1—H1	108.8	C13—C12—N3	118.2 (2)
C6—C1—H1	108.8	C11—C12—N3	118.4 (2)
C1—C2—C3	106.9 (2)	C12—C13—C14	117.8 (2)
C1—C2—H2A	110.3	C12—C13—H13	121.1
C3—C2—H2A	110.3	C14—C13—H13	121.1
C1—C2—H2B	110.3	C9—C14—C13	119.7 (2)
C3—C2—H2B	110.3	C9—C14—H14	120.2
H2A—C2—H2B	108.6	C13—C14—H14	120.2
C2—C3—C4	113.1 (2)	O7—C15—O6	125.4 (2)
C2—C3—H3A	109.0	O7—C15—N1	123.3 (2)
C4—C3—H3A	108.9	O6—C15—N1	111.2 (2)
C2—C3—H3B	108.9	C17—C16—C21	123.1 (2)
C4—C3—H3B	108.9	C17—C16—O6	118.4 (2)
H3A—C3—H3B	107.8	C21—C16—O6	118.3 (2)
C5—C4—C3	113.5 (2)	C16—C17—C18	118.2 (2)
C5—C4—H4A	108.9	C16—C17—H17	120.9
C3—C4—H4A	108.9	C18—C17—H17	120.9
C5—C4—H4B	108.9	C19—C18—C17	118.1 (2)
C3—C4—H4B	108.9	C19—C18—H18	120.9
H4A—C4—H4B	107.7	C17—C18—H18	120.9
C6—C5—C4	106.7 (2)	C18—C19—C20	123.8 (2)
C6—C5—H5A	110.4	C18—C19—N4	118.1 (2)
C4—C5—H5A	110.4	C20—C19—N4	118.1 (2)
C6—C5—H5B	110.4	C19—C20—C21	118.0 (2)
C4—C5—H5B	110.4	C19—C20—H20	121.0
H5A—C5—H5B	108.6	C21—C20—H20	121.0
N2—C6—C5	121.2 (2)	C16—C21—C20	118.7 (2)
N2—C6—C1	100.43 (19)	C16—C21—H21	120.6
C5—C6—C1	109.19 (18)	C20—C21—H21	120.6
N2—C6—H6	108.4	C15—N1—C7	123.6 (2)
C5—C6—H6	108.4	C15—N1—C1	119.72 (19)
C1—C6—H6	108.4	C7—N1—C1	110.17 (19)
O1—C7—N1	127.0 (2)	C8—N2—C7	124.80 (19)
O1—C7—N2	127.3 (2)	C8—N2—C6	120.69 (19)
N1—C7—N2	105.78 (19)	C7—N2—C6	109.51 (19)
O2—C8—O3	124.8 (2)	O4—N3—O5	123.5 (2)
O2—C8—N2	123.1 (2)	O4—N3—C12	118.0 (2)
O3—C8—N2	112.2 (2)	O5—N3—C12	118.4 (2)
C14—C9—C10	122.5 (2)	O9—N4—O8	123.9 (2)
C14—C9—O3	116.7 (2)	O9—N4—C19	118.6 (2)
C10—C9—O3	120.5 (2)	O8—N4—C19	117.5 (2)
C9—C10—C11	118.3 (2)	C8—O3—C9	116.79 (19)
C9—C10—H10	120.9	C15—O6—C16	115.47 (17)
C11—C10—H10	120.9

N1—C1—C2—C3	−177.3 (2)	N2—C7—N1—C15	−162.8 (2)
C6—C1—C2—C3	−61.9 (3)	O1—C7—N1—C1	168.4 (2)
C1—C2—C3—C4	53.0 (3)	N2—C7—N1—C1	−11.4 (3)
C2—C3—C4—C5	−51.1 (3)	C2—C1—N1—C15	−57.4 (3)
C3—C4—C5—C6	53.6 (3)	C6—C1—N1—C15	−177.4 (2)
C4—C5—C6—N2	−177.9 (2)	C2—C1—N1—C7	149.8 (2)
C4—C5—C6—C1	−62.1 (3)	C6—C1—N1—C7	29.9 (3)
N1—C1—C6—N2	−34.9 (2)	O2—C8—N2—C7	161.2 (2)
C2—C1—C6—N2	−161.84 (19)	O3—C8—N2—C7	−20.9 (3)
N1—C1—C6—C5	−163.4 (2)	O2—C8—N2—C6	8.9 (3)
C2—C1—C6—C5	69.7 (3)	O3—C8—N2—C6	−173.17 (18)
C14—C9—C10—C11	1.8 (4)	O1—C7—N2—C8	12.1 (4)
O3—C9—C10—C11	−172.1 (2)	N1—C7—N2—C8	−168.1 (2)
C9—C10—C11—C12	1.4 (4)	O1—C7—N2—C6	167.0 (2)
C10—C11—C12—C13	−3.5 (4)	N1—C7—N2—C6	−13.2 (2)
C10—C11—C12—N3	176.6 (2)	C5—C6—N2—C8	−52.9 (3)
C11—C12—C13—C14	2.3 (4)	C1—C6—N2—C8	−173.1 (2)
N3—C12—C13—C14	−177.8 (2)	C5—C6—N2—C7	151.0 (2)
C10—C9—C14—C13	−3.0 (4)	C1—C6—N2—C7	30.8 (2)
O3—C9—C14—C13	171.1 (2)	C13—C12—N3—O4	−173.2 (2)
C12—C13—C14—C9	1.0 (4)	C11—C12—N3—O4	6.7 (3)
C21—C16—C17—C18	0.6 (4)	C13—C12—N3—O5	7.6 (3)
O6—C16—C17—C18	175.2 (2)	C11—C12—N3—O5	−172.5 (2)
C16—C17—C18—C19	−0.1 (3)	C18—C19—N4—O9	−168.4 (2)
C17—C18—C19—C20	0.3 (4)	C20—C19—N4—O9	10.7 (3)
C17—C18—C19—N4	179.4 (2)	C18—C19—N4—O8	10.1 (3)
C18—C19—C20—C21	−0.8 (4)	C20—C19—N4—O8	−170.7 (2)
N4—C19—C20—C21	−179.9 (2)	O2—C8—O3—C9	−5.8 (3)
C17—C16—C21—C20	−1.1 (4)	N2—C8—O3—C9	176.2 (2)
O6—C16—C21—C20	−175.8 (2)	C14—C9—O3—C8	113.1 (2)
C19—C20—C21—C16	1.2 (3)	C10—C9—O3—C8	−72.7 (3)
O7—C15—N1—C7	146.1 (3)	O7—C15—O6—C16	−14.2 (4)
O6—C15—N1—C7	−36.0 (3)	N1—C15—O6—C16	167.9 (2)
O7—C15—N1—C1	−2.8 (4)	C17—C16—O6—C15	106.5 (3)
O6—C15—N1—C1	175.1 (2)	C21—C16—O6—C15	−78.6 (3)
O1—C7—N1—C15	16.9 (4)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₄O₉
M_r	470.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	90
a, b, c (Å)	6.059 (1), 17.956 (3), 18.982 (3)
V (Å³)	2065.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.35 × 0.20 × 0.10

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.959, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9218, 2724, 2209
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.103, 1.04
No. of reflections	2724
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.31

Computer programs: COLLECT (Nonius, 2002), SCALEPACK (Otwinowski & Minor, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), XP in SHELXTL (Sheldrick, 1995), SHELXL97 (Sheldrick, 1997) and local procedures.

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(3aR,7aR)-Bis(4-nitro­phen­yl) 2-oxo­perhydro­benzo[d]imidazole-1,3-di­carboxyl­ate

Supporting information

Key indicators

checkCIF/PLATON results

(3aR,7aR)-Bis(4-nitrophenyl) 2-oxoperhydrobenzo[d]imidazole-1,3-dicarboxylate