trans-Cyclo­hexane-1,4-diyl bis­(4-nitro­phen­yl) dicarbonate

Nawazish Ali, S.; Begum, S.; Winnik, M.A.; Lough, A.J.

doi:10.1107/S1600536807066007

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o282

https://doi.org/10.1107/S1600536807066007

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trans-Cyclohexane-1,4-diyl bis(4-nitrophenyl) dicarbonate

Syed Nawazish Ali,^a,^b Sabira Begum,^a Mitchell A. Winnik ^b and Alan J. Lough ^b ^*

^aH. E. J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 3 December 2007; accepted 6 December 2007; online 18 December 2007)

In the title crystal structure, C₂₀H₁₈N₂O₁₀, there are two independent molecules, both of which lie on crystallographic inversion centres. In one molecule the 4-nitrophenyl dicarbonate groups are substituted in equatorial (A_eq) positions of the chair-form cyclohexane ring while in the other molecule the substitution is axial (B_ax). The dihedral angles between the atoms of the symmetry-unique carbonate group (O=CO₂—) and benzene ring for each molecule are 47.3 (1)° for A_eq and 11.7 (2)° for B_ax. In B_ax, this facilitates the formation of a weak intramolecular C—H⋯O hydrogen bond, while the packing is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For related literature, see: Ali et al. (2008 ).

Experimental

Crystal data

C₂₀H₁₈N₂O₁₀
M_r = 446.36
Triclinic, $[P \overline 1]$
a = 7.6804 (14) Å
b = 11.6548 (18) Å
c = 12.3092 (11) Å
α = 63.201 (8)°
β = 87.254 (10)°
γ = 82.310 (7)°
V = 974.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 150 (1) K
0.22 × 0.20 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.768, T_max = 0.996
7088 measured reflections
3355 independent reflections
1633 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.190
S = 0.96
3355 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10A—H10A⋯O5Aⁱ	0.95	2.32	3.205 (6)	155
C6B—H6BA⋯O2B	0.95	2.24	2.812 (5)	118
C9B—H9BA⋯O2Aⁱⁱ	0.95	2.48	3.184 (5)	131
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z.

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL/PC.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807066007/hb2675sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066007/hb2675Isup2.hkl

checkCIF report

Comment top

The synthesis of title compound is similar to that of cyclohex-2-ene-1,4-diylbis(4-nitrophenyl)dicarbonate (Ali et al., 2008). Here, we used a mixture of cis and trans isomers of cyclohexane-1,4-diol. The trans isomer has been separated from the mixture of cis and trans isomers. Most of the trans isomer remained undissolved in EtOH during the recrystallization at 358 K, after 40 minutes. Pale yellow plates of (I) were obtained after solubilizing this EtOH insoluble solid in dichloromethane. The molecular structure is illustrated in Figs. 1 and 2, showing that one of the two asymmetric molecules possesses equatorial substituents and the other axial. Within the latter, a weak C—H···O interaction (Table 1) occurs. Further C—H···O links help to establish the packing.

Related literature top

For related literature, see: Ali et al. (2008); Spek (2003).

Experimental top

A solution of 4-nitrophenylchloroformate (5.64 g, 28.0 mmol) in dry dichloromethane (40 ml) was added dropwise via a 100 ml separating funnel into a solution of cyclohexane-1,4-diol (cis and trans isomers) (1.63 g, 14.0 mmol) in anhydrous pyridine (2.15 g, 2.2 ml, 27.1 mmol) and dry dichloromethane (20 ml) in a 250 ml round-bottom flask. A white suspension appeared which was allowed to stir gently at room temperature for 16 h. After this time more dry dichloromethane (40 ml) was added, which dissolved the suspension and then the reaction mixture was stirred for another 6 h. Then it was quenched by adding deionized water (40 ml). The reaction mixture was transferred to a separating funnel (500 ml), and the lower organic phase was removed. The aqueous phase was washed with dichloromethane (30 ml × 2), and the dichloromethane solutions were combined. These were then washed with deionized water (30 ml × 2), a 1.0% solution of acetic acid (50 ml × 2) and once more with deionized water (40 ml × 2), and then dried over anhydrous magnesium sulfate and filtered. After filtration, the solvent was removed by rotary evaporator. The product was dried in air overnight in a fume hood and then in a vacuum oven for 24 h at room temperature (< 1 Torr). The desired product was obtained in good yield (6.2 g, 84.0%) as a white solid. For recrystallization, the solid was dissolved in 95% EtOH (50 ml) at 358 K, after 40 minutes some of the solid (about 40%) remained undissolved. The warm solution was filtered and the EtOH-insoluble solid was recovered from the filter paper and dissolved in dichloromethane. Pale yellow plates of (I) were obtained by slow evaporation of solvent at room temperature.

Structure description top

For related literature, see: Ali et al. (2008); Spek (2003).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2001).

Figures top

	Fig. 1. View of one of the independent molecules of the title compound with displacement ellipsoids drawn at the 30% probability level. Unlabeled atoms are related by the symmetry operator (-x, -y, 1 - z).
	Fig. 2. View of the other independent molecule of the title compound with displacement ellipsoids drawn at the 30% probability level. Unlabeled atoms are related by the symmetry operator (2 - x, 1 - y, -z). The dashed line indicates a hydrogen bond.

trans-Cyclohexane-1,4-diyl bis(4-nitrophenyl) dicarbonate top

Crystal data top

C₂₀H₁₈N₂O₁₀	Z = 2
M_r = 446.36	F(000) = 464
Triclinic, P1	D_x = 1.521 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6804 (14) Å	Cell parameters from 7088 reflections
b = 11.6548 (18) Å	θ = 2.7–25.2°
c = 12.3092 (11) Å	µ = 0.12 mm⁻¹
α = 63.201 (8)°	T = 150 K
β = 87.254 (10)°	Plate, pale yellow
γ = 82.310 (7)°	0.22 × 0.20 × 0.08 mm
V = 974.6 (3) Å³

Data collection top

Nonius KappaCCD diffractometer	3355 independent reflections
Radiation source: fine-focus sealed tube	1633 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
Detector resolution: 9 pixels mm^-1	θ_max = 25.2°, θ_min = 2.7°
φ scans and ω scans with κ offsets	h = −9→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→13
T_min = 0.768, T_max = 0.996	l = −14→14
7088 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0923P)²] where P = (F_o² + 2F_c²)/3
3355 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O₁₀	γ = 82.310 (7)°
M_r = 446.36	V = 974.6 (3) Å³
Triclinic, P1	Z = 2
a = 7.6804 (14) Å	Mo Kα radiation
b = 11.6548 (18) Å	µ = 0.12 mm⁻¹
c = 12.3092 (11) Å	T = 150 K
α = 63.201 (8)°	0.22 × 0.20 × 0.08 mm
β = 87.254 (10)°

Data collection top

Nonius KappaCCD diffractometer	3355 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1633 reflections with I > 2σ(I)
T_min = 0.768, T_max = 0.996	R_int = 0.080
7088 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.190	H-atom parameters constrained
S = 0.96	Δρ_max = 0.30 e Å⁻³
3355 reflections	Δρ_min = −0.27 e Å⁻³
289 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
O1A	0.1429 (4)	0.0985 (3)	0.2676 (2)	0.0517 (8)
O2A	0.4182 (4)	−0.0092 (3)	0.2921 (2)	0.0504 (8)
O3A	0.3173 (4)	0.1684 (3)	0.1182 (2)	0.0524 (8)
O4A	0.9007 (4)	0.1716 (3)	−0.2527 (3)	0.0685 (10)
O5A	1.0631 (5)	0.1300 (3)	−0.0977 (3)	0.0690 (10)
N1A	0.9198 (6)	0.1542 (3)	−0.1481 (4)	0.0498 (10)
C1A	−0.1660 (6)	−0.0576 (4)	0.5216 (3)	0.0495 (12)
H1A1	−0.1245	−0.1509	0.5502	0.059*
H1A2	−0.2960	−0.0463	0.5211	0.059*
C2A	−0.1003 (6)	0.0194 (4)	0.3939 (3)	0.0513 (12)
H2A1	−0.1389	−0.0145	0.3396	0.062*
H2A2	−0.1520	0.1112	0.3624	0.062*
C3A	0.0979 (6)	0.0112 (4)	0.3927 (3)	0.0474 (12)
H3A	0.1518	−0.0796	0.4145	0.057*
C4A	0.3057 (6)	0.0763 (4)	0.2341 (4)	0.0453 (11)
C5A	0.4739 (6)	0.1635 (4)	0.0559 (3)	0.0409 (11)
C6A	0.6345 (6)	0.1517 (4)	0.1054 (4)	0.0476 (12)
H6AA	0.6442	0.1459	0.1844	0.057*
C7A	0.7824 (6)	0.1483 (4)	0.0383 (4)	0.0478 (11)
H7AA	0.8962	0.1381	0.0709	0.057*
C8A	0.7621 (6)	0.1599 (4)	−0.0766 (3)	0.0402 (10)
C9A	0.6019 (6)	0.1746 (4)	−0.1267 (3)	0.0459 (11)
H9AA	0.5926	0.1831	−0.2068	0.055*
C10A	0.4527 (6)	0.1771 (4)	−0.0601 (3)	0.0455 (11)
H10A	0.3391	0.1878	−0.0932	0.055*
O1B	0.9940 (4)	0.5357 (3)	0.1688 (2)	0.0493 (8)
O2B	0.9203 (4)	0.3799 (3)	0.3498 (2)	0.0568 (9)
O3B	0.8673 (4)	0.5951 (3)	0.2963 (2)	0.0486 (8)
O4B	0.4719 (5)	0.5191 (3)	0.7792 (3)	0.0708 (11)
O5B	0.4665 (5)	0.7279 (4)	0.6849 (3)	0.0731 (11)
N1B	0.5072 (5)	0.6198 (4)	0.6918 (3)	0.0527 (10)
C1B	0.8165 (6)	0.4921 (4)	−0.0214 (4)	0.0507 (12)
H1B1	0.7325	0.4509	−0.0465	0.061*
H1B2	0.7480	0.5565	0.0008	0.061*
C2B	0.9217 (6)	0.3884 (4)	0.0905 (3)	0.0500 (12)
H2B1	0.8409	0.3535	0.1597	0.060*
H2B2	0.9730	0.3162	0.0728	0.060*
C3B	1.0669 (6)	0.4393 (4)	0.1269 (3)	0.0497 (12)
H3B	1.1392	0.3659	0.1938	0.060*
C4B	0.9251 (6)	0.4897 (4)	0.2793 (4)	0.0474 (11)
C5B	0.7791 (6)	0.5888 (4)	0.4005 (3)	0.0425 (11)
C6B	0.7732 (6)	0.4775 (4)	0.5097 (3)	0.0457 (11)
H6BA	0.8299	0.3960	0.5189	0.055*
C7B	0.6813 (6)	0.4894 (4)	0.6054 (4)	0.0473 (11)
H7BA	0.6735	0.4149	0.6810	0.057*
C8B	0.6022 (6)	0.6085 (4)	0.5905 (3)	0.0412 (10)
C9B	0.6109 (6)	0.7178 (4)	0.4819 (3)	0.0439 (11)
H9BA	0.5554	0.7996	0.4727	0.053*
C10B	0.7007 (6)	0.7072 (4)	0.3872 (3)	0.0405 (10)
H10B	0.7085	0.7822	0.3120	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.052 (2)	0.0532 (18)	0.0391 (16)	0.0002 (15)	0.0040 (14)	−0.0132 (14)
O2A	0.052 (2)	0.0445 (17)	0.0441 (16)	0.0074 (16)	−0.0042 (15)	−0.0133 (13)
O3A	0.055 (2)	0.0517 (17)	0.0347 (16)	0.0048 (15)	0.0035 (14)	−0.0093 (14)
O4A	0.061 (3)	0.087 (2)	0.072 (2)	−0.0174 (19)	0.0189 (18)	−0.048 (2)
O5A	0.045 (2)	0.064 (2)	0.078 (2)	−0.0100 (18)	0.0049 (19)	−0.0146 (17)
N1A	0.047 (3)	0.040 (2)	0.059 (3)	−0.0088 (19)	0.004 (2)	−0.0180 (18)
C1A	0.051 (3)	0.052 (3)	0.045 (2)	−0.015 (2)	0.003 (2)	−0.019 (2)
C2A	0.056 (3)	0.062 (3)	0.039 (2)	−0.008 (2)	−0.001 (2)	−0.025 (2)
C3A	0.055 (3)	0.051 (3)	0.036 (2)	−0.007 (2)	0.001 (2)	−0.019 (2)
C4A	0.049 (3)	0.046 (3)	0.044 (3)	−0.006 (2)	0.008 (2)	−0.025 (2)
C5A	0.043 (3)	0.035 (2)	0.041 (2)	−0.003 (2)	0.010 (2)	−0.0155 (18)
C6A	0.055 (3)	0.048 (3)	0.042 (2)	−0.003 (2)	−0.007 (2)	−0.022 (2)
C7A	0.043 (3)	0.048 (3)	0.052 (3)	−0.007 (2)	−0.005 (2)	−0.021 (2)
C8A	0.042 (3)	0.032 (2)	0.044 (2)	−0.0007 (19)	0.002 (2)	−0.0166 (18)
C9A	0.054 (3)	0.045 (2)	0.035 (2)	−0.010 (2)	−0.001 (2)	−0.0141 (19)
C10A	0.040 (3)	0.050 (3)	0.039 (2)	−0.008 (2)	0.000 (2)	−0.0126 (19)
O1B	0.059 (2)	0.0453 (16)	0.0435 (17)	−0.0044 (15)	0.0073 (14)	−0.0209 (13)
O2B	0.079 (3)	0.0435 (19)	0.0430 (17)	−0.0046 (16)	0.0087 (15)	−0.0169 (15)
O3B	0.063 (2)	0.0411 (17)	0.0404 (16)	−0.0016 (15)	0.0082 (14)	−0.0194 (13)
O4B	0.077 (3)	0.075 (2)	0.0455 (19)	−0.004 (2)	0.0170 (17)	−0.0174 (17)
O5B	0.084 (3)	0.072 (2)	0.079 (2)	−0.009 (2)	0.0228 (19)	−0.050 (2)
N1B	0.048 (3)	0.064 (3)	0.048 (2)	−0.003 (2)	0.0061 (18)	−0.029 (2)
C1B	0.051 (3)	0.049 (3)	0.054 (3)	−0.002 (2)	0.005 (2)	−0.027 (2)
C2B	0.066 (3)	0.045 (3)	0.042 (2)	−0.009 (2)	0.009 (2)	−0.022 (2)
C3B	0.066 (3)	0.042 (2)	0.042 (2)	−0.003 (2)	0.004 (2)	−0.021 (2)
C4B	0.060 (3)	0.043 (3)	0.036 (2)	−0.008 (2)	−0.001 (2)	−0.014 (2)
C5B	0.046 (3)	0.047 (3)	0.035 (2)	−0.007 (2)	−0.0012 (19)	−0.0187 (19)
C6B	0.048 (3)	0.039 (2)	0.051 (3)	0.002 (2)	0.000 (2)	−0.022 (2)
C7B	0.048 (3)	0.047 (3)	0.041 (2)	−0.008 (2)	0.001 (2)	−0.015 (2)
C8B	0.038 (3)	0.046 (3)	0.040 (2)	−0.005 (2)	0.0024 (19)	−0.020 (2)
C9B	0.043 (3)	0.043 (2)	0.050 (3)	−0.003 (2)	−0.003 (2)	−0.025 (2)
C10B	0.045 (3)	0.041 (2)	0.037 (2)	−0.010 (2)	0.0005 (19)	−0.0180 (19)

Geometric parameters (Å, º) top

O1A—C4A	1.327 (5)	O1B—C4B	1.328 (5)
O1A—C3A	1.469 (4)	O1B—C3B	1.472 (5)
O2A—C4A	1.199 (5)	O2B—C4B	1.184 (5)
O3A—C4A	1.352 (5)	O3B—C4B	1.352 (5)
O3A—C5A	1.404 (5)	O3B—C5B	1.398 (5)
O4A—N1A	1.223 (4)	O4B—N1B	1.236 (4)
O5A—N1A	1.224 (5)	O5B—N1B	1.222 (5)
N1A—C8A	1.475 (5)	N1B—C8B	1.463 (5)
C1A—C2A	1.518 (5)	C1B—C3Bⁱⁱ	1.507 (5)
C1A—C3Aⁱ	1.525 (6)	C1B—C2B	1.535 (5)
C1A—H1A1	0.9900	C1B—H1B1	0.9900
C1A—H1A2	0.9900	C1B—H1B2	0.9900
C2A—C3A	1.512 (6)	C2B—C3B	1.503 (6)
C2A—H2A1	0.9900	C2B—H2B1	0.9900
C2A—H2A2	0.9900	C2B—H2B2	0.9900
C3A—C1Aⁱ	1.525 (6)	C3B—C1Bⁱⁱ	1.507 (5)
C3A—H3A	1.0000	C3B—H3B	1.0000
C5A—C6A	1.365 (6)	C5B—C10B	1.370 (5)
C5A—C10A	1.379 (6)	C5B—C6B	1.388 (5)
C6A—C7A	1.379 (6)	C6B—C7B	1.395 (6)
C6A—H6AA	0.9500	C6B—H6BA	0.9500
C7A—C8A	1.373 (5)	C7B—C8B	1.373 (6)
C7A—H7AA	0.9500	C7B—H7BA	0.9500
C8A—C9A	1.358 (6)	C8B—C9B	1.375 (5)
C9A—C10A	1.381 (6)	C9B—C10B	1.372 (5)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—H10A	0.9500	C10B—H10B	0.9500

C4A—O1A—C3A	116.0 (3)	C4B—O1B—C3B	116.4 (3)
C4A—O3A—C5A	118.0 (3)	C4B—O3B—C5B	123.4 (3)
O4A—N1A—O5A	123.8 (4)	O5B—N1B—O4B	123.8 (4)
O4A—N1A—C8A	118.7 (4)	O5B—N1B—C8B	118.3 (4)
O5A—N1A—C8A	117.5 (4)	O4B—N1B—C8B	117.8 (4)
C2A—C1A—C3Aⁱ	109.7 (3)	C3Bⁱⁱ—C1B—C2B	112.3 (4)
C2A—C1A—H1A1	109.7	C3Bⁱⁱ—C1B—H1B1	109.1
C3Aⁱ—C1A—H1A1	109.7	C2B—C1B—H1B1	109.1
C2A—C1A—H1A2	109.7	C3Bⁱⁱ—C1B—H1B2	109.1
C3Aⁱ—C1A—H1A2	109.7	C2B—C1B—H1B2	109.1
H1A1—C1A—H1A2	108.2	H1B1—C1B—H1B2	107.9
C3A—C2A—C1A	111.1 (3)	C3B—C2B—C1B	112.9 (4)
C3A—C2A—H2A1	109.4	C3B—C2B—H2B1	109.0
C1A—C2A—H2A1	109.4	C1B—C2B—H2B1	109.0
C3A—C2A—H2A2	109.4	C3B—C2B—H2B2	109.0
C1A—C2A—H2A2	109.4	C1B—C2B—H2B2	109.0
H2A1—C2A—H2A2	108.0	H2B1—C2B—H2B2	107.8
O1A—C3A—C2A	105.7 (3)	O1B—C3B—C2B	110.5 (4)
O1A—C3A—C1Aⁱ	108.5 (3)	O1B—C3B—C1Bⁱⁱ	106.1 (3)
C2A—C3A—C1Aⁱ	111.9 (4)	C2B—C3B—C1Bⁱⁱ	111.9 (3)
O1A—C3A—H3A	110.2	O1B—C3B—H3B	109.4
C2A—C3A—H3A	110.2	C2B—C3B—H3B	109.4
C1Aⁱ—C3A—H3A	110.2	C1Bⁱⁱ—C3B—H3B	109.4
O2A—C4A—O1A	127.8 (4)	O2B—C4B—O1B	127.6 (4)
O2A—C4A—O3A	126.7 (4)	O2B—C4B—O3B	127.0 (4)
O1A—C4A—O3A	105.5 (4)	O1B—C4B—O3B	105.3 (3)
C6A—C5A—C10A	122.8 (4)	C10B—C5B—C6B	121.5 (4)
C6A—C5A—O3A	122.0 (4)	C10B—C5B—O3B	113.0 (3)
C10A—C5A—O3A	115.1 (4)	C6B—C5B—O3B	125.5 (4)
C5A—C6A—C7A	118.6 (4)	C5B—C6B—C7B	117.8 (4)
C5A—C6A—H6AA	120.7	C5B—C6B—H6BA	121.1
C7A—C6A—H6AA	120.7	C7B—C6B—H6BA	121.1
C8A—C7A—C6A	118.8 (4)	C8B—C7B—C6B	120.1 (4)
C8A—C7A—H7AA	120.6	C8B—C7B—H7BA	120.0
C6A—C7A—H7AA	120.6	C6B—C7B—H7BA	120.0
C9A—C8A—C7A	122.5 (4)	C7B—C8B—C9B	121.2 (4)
C9A—C8A—N1A	118.4 (4)	C7B—C8B—N1B	119.6 (3)
C7A—C8A—N1A	119.0 (4)	C9B—C8B—N1B	119.2 (4)
C8A—C9A—C10A	119.3 (4)	C10B—C9B—C8B	119.2 (4)
C8A—C9A—H9AA	120.3	C10B—C9B—H9BA	120.4
C10A—C9A—H9AA	120.3	C8B—C9B—H9BA	120.4
C5A—C10A—C9A	117.9 (4)	C5B—C10B—C9B	120.2 (3)
C5A—C10A—H10A	121.0	C5B—C10B—H10B	119.9
C9A—C10A—H10A	121.0	C9B—C10B—H10B	119.9

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10A—H10A···O5Aⁱⁱⁱ	0.95	2.32	3.205 (6)	155
C6B—H6BA···O2B	0.95	2.24	2.812 (5)	118
C9B—H9BA···O2A^iv	0.95	2.48	3.184 (5)	131

Symmetry codes: (iii) x−1, y, z; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O₁₀
M_r	446.36
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	7.6804 (14), 11.6548 (18), 12.3092 (11)
α, β, γ (°)	63.201 (8), 87.254 (10), 82.310 (7)
V (Å³)	974.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.22 × 0.20 × 0.08

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.768, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	7088, 3355, 1633
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.190, 0.96
No. of reflections	3355
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.27

Computer programs: COLLECT (Nonius, 2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL/PC (Sheldrick, 2001), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10A—H10A···O5Aⁱ	0.95	2.32	3.205 (6)	155
C6B—H6BA···O2B	0.95	2.24	2.812 (5)	118
C9B—H9BA···O2Aⁱⁱ	0.95	2.48	3.184 (5)	131

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

Acknowledgements

The authors acknowledge funding from the Higher Education Commission (HEC) of Pakistan, Materials and Manufacturing Ontario (MMO), Canada, NSERC Canada and the University of Toronto.

References

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