Bis(4-nitro­phen­yl) 1,3-phenyl­ene­dimethyl­ene dicarbonate

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

doi:10.1107/S1600536808006132

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o692

doi:10.1107/S1600536808006132

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Bis(4-nitrophenyl) 1,3-phenylenedimethylene dicarbonate

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

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

(Received 20 February 2008; accepted 5 March 2008; online 12 March 2008)

In the title molecule, C₂₂H₁₆N₂O₁₀, the dihedral angles between the benzene rings of the 4-nitrophenyl groups and the central benzene ring are 32.7 (1) and 34.7 (1)°, while the dihedral angle between the two benzene rings of the 4-nitrophenyl groups is 3.6 (2)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules into centrosymmetric dimers.

Related literature

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

Experimental

Crystal data

C₂₂H₁₆N₂O₁₀
M_r = 468.37
Triclinic, $[P \overline 1]$
a = 8.5956 (4) Å
b = 9.2367 (5) Å
c = 14.1550 (8) Å
α = 94.094 (2)°
β = 107.134 (3)°
γ = 105.674 (3)°
V = 1020.00 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 150 (1) K
0.34 × 0.20 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.808, T_max = 0.980
10107 measured reflections
4580 independent reflections
3182 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.166
S = 1.15
4580 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O10ⁱ	0.95	2.55	3.134 (4)	120
C15—H15B⋯O9ⁱ	0.99	2.58	3.504 (4)	155
C21—H21A⋯O7ⁱ	0.95	2.50	3.264 (3)	138
Symmetry code: (i) -x+1, -y+1, -z+2.

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 (Sheldrick, 2008 ); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006132/cf2186sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006132/cf2186Isup2.hkl

checkCIF report

Comment top

For background information and relevant references see Ali et al. (2008). In the title molecule (Fig. 1) the dihedral angles between the benzene rings of the p-nitrophenyl groups and the central benzene ring are 32.7 (1) (for C9—C14) and 34.7 (1)° (for C17—C22), while the dihedral angle between the two benzene rings of the p-nitrophenyl groups is 3.6 (2)°. In the crystal structure, weak intermolecluar C—H···O hydrogen bonds link molecules into centrosymmetric dimers (Fig. 2).

Related literature top

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

Experimental top

A solution of 4-nitrophenylchloroformate (14.1 g, 70 mmol) in dry dichloromethane (70 ml) was added dropwise via a 250 ml separatory funnel to a solution of 1,3-phenylenedimethanol (4.82 g, 35 mmol) in anhydrous pyridine (5.38 g, 5.5 ml, 68.0 mmol) and dry dichloromethane (20 ml) in a 250 ml round-bottom flask. A white suspension appeared which was stirred gently at room temperature for 10 h. After this time more dry dichloromethane (50 ml) was added, which dissolved the suspension and then the reaction mixture was stirred for another 6 h. It was then quenched by adding deionized water (50 ml). The reaction mixture was transferred to a separatory funnel (500 ml), and the lower organic phase was removed. The aqueous phase was washed with dichloromethane (30 ml x 3), and all the dichloromethane solutions were combined. These were then washed with deionized water (40 ml x 3), a 1.0% solution of acetic acid (50 ml x 4) and once more with deionized water (40 ml x 3), 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 a moderate yield (11.4 g, 70.0%) as a white solid; the product was recrystallized by dissolving in a mixture of dichloromethane and ethanol (95%) (1:1). The reaction mixture was heated at 358 K, and filtered after 40 minutes. X-ray quality crystals were obtained after slow evaporation of the solvent at room temperature.

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 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure with weak intermolecular C—H···O hydrogen bonds shown as dashed lines.

Bis(4-nitrophenyl) 1,3-phenylenedimethylene dicarbonate top

Crystal data top

C₂₂H₁₆N₂O₁₀	Z = 2
M_r = 468.37	F(000) = 484
Triclinic, P1	D_x = 1.525 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5956 (4) Å	Cell parameters from 10107 reflections
b = 9.2367 (5) Å	θ = 2.6–27.5°
c = 14.1550 (8) Å	µ = 0.12 mm⁻¹
α = 94.094 (2)°	T = 150 K
β = 107.134 (3)°	Block, colourless
γ = 105.674 (3)°	0.34 × 0.20 × 0.20 mm
V = 1020.00 (10) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	4580 independent reflections
Radiation source: fine-focus sealed tube	3182 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ϕ scans and ω scans with κ offsets	h = −11→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
T_min = 0.808, T_max = 0.980	l = −18→18
10107 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H-atom parameters constrained
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.035P)² + 1.3721P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
4580 reflections	Δρ_max = 0.30 e Å⁻³
308 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (4)

Crystal data top

C₂₂H₁₆N₂O₁₀	γ = 105.674 (3)°
M_r = 468.37	V = 1020.00 (10) Å³
Triclinic, P1	Z = 2
a = 8.5956 (4) Å	Mo Kα radiation
b = 9.2367 (5) Å	µ = 0.12 mm⁻¹
c = 14.1550 (8) Å	T = 150 K
α = 94.094 (2)°	0.34 × 0.20 × 0.20 mm
β = 107.134 (3)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	4580 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	3182 reflections with I > 2σ(I)
T_min = 0.808, T_max = 0.980	R_int = 0.054
10107 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.15	Δρ_max = 0.30 e Å⁻³
4580 reflections	Δρ_min = −0.26 e Å⁻³
308 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
O1	0.8872 (3)	0.1353 (2)	0.51451 (16)	0.0340 (5)
O2	0.6463 (3)	0.2045 (3)	0.48906 (18)	0.0406 (6)
O3	0.8682 (3)	0.3232 (2)	0.43660 (16)	0.0339 (5)
O4	0.5734 (3)	0.8621 (3)	0.32218 (18)	0.0493 (7)
O5	0.5700 (3)	0.7631 (3)	0.17823 (17)	0.0453 (6)
O6	0.7702 (3)	0.1855 (2)	0.94414 (15)	0.0321 (5)
O7	0.7572 (3)	0.4000 (2)	1.02591 (16)	0.0346 (5)
O8	0.6017 (3)	0.1596 (2)	1.03074 (15)	0.0304 (5)
O9	0.1915 (5)	0.4431 (4)	1.2504 (3)	0.0781 (10)
O10	0.2930 (3)	0.3121 (3)	1.35819 (18)	0.0490 (7)
N1	0.6000 (3)	0.7673 (3)	0.26870 (19)	0.0343 (6)
N2	0.2722 (4)	0.3547 (3)	1.2770 (2)	0.0413 (7)
C1	0.8609 (4)	0.1437 (3)	0.7314 (2)	0.0289 (6)
H1A	0.7826	0.1949	0.6996	0.035*
C2	0.9034 (4)	0.0426 (3)	0.6733 (2)	0.0269 (6)
C3	1.0188 (4)	−0.0314 (4)	0.7203 (2)	0.0326 (7)
H3A	1.0505	−0.0993	0.6814	0.039*
C4	1.0875 (4)	−0.0059 (4)	0.8237 (2)	0.0388 (8)
H4A	1.1658	−0.0571	0.8556	0.047*
C5	1.0431 (4)	0.0932 (4)	0.8811 (2)	0.0363 (7)
H5A	1.0893	0.1082	0.9521	0.044*
C6	0.9314 (4)	0.1712 (3)	0.8356 (2)	0.0313 (7)
C7	0.8208 (4)	0.0058 (3)	0.5615 (2)	0.0333 (7)
H7A	0.8443	−0.0854	0.5354	0.040*
H7B	0.6954	−0.0173	0.5444	0.040*
C8	0.7845 (4)	0.2182 (3)	0.4820 (2)	0.0300 (6)
C9	0.7965 (4)	0.4351 (3)	0.3983 (2)	0.0288 (6)
C10	0.7170 (4)	0.5092 (3)	0.4481 (2)	0.0311 (7)
H10A	0.7052	0.4839	0.5100	0.037*
C11	0.6548 (4)	0.6215 (3)	0.4058 (2)	0.0314 (7)
H11A	0.6008	0.6758	0.4387	0.038*
C12	0.6728 (4)	0.6530 (3)	0.3153 (2)	0.0287 (6)
C13	0.7562 (4)	0.5817 (4)	0.2664 (2)	0.0320 (7)
H13A	0.7691	0.6080	0.2049	0.038*
C14	0.8204 (4)	0.4712 (3)	0.3092 (2)	0.0310 (7)
H14A	0.8799	0.4208	0.2781	0.037*
C15	0.8850 (4)	0.2793 (4)	0.8979 (3)	0.0382 (8)
H15A	0.9887	0.3477	0.9501	0.046*
H15B	0.8267	0.3424	0.8556	0.046*
C16	0.7147 (4)	0.2644 (3)	1.0016 (2)	0.0269 (6)
C17	0.5156 (4)	0.2113 (3)	1.0894 (2)	0.0261 (6)
C18	0.5105 (4)	0.1426 (3)	1.1723 (2)	0.0284 (6)
H18A	0.5621	0.0642	1.1865	0.034*
C19	0.4293 (4)	0.1892 (3)	1.2346 (2)	0.0295 (6)
H19A	0.4271	0.1461	1.2933	0.035*
C20	0.3518 (4)	0.2999 (3)	1.2088 (2)	0.0294 (6)
C21	0.3483 (4)	0.3636 (3)	1.1233 (2)	0.0312 (7)
H21A	0.2898	0.4368	1.1067	0.037*
C22	0.4322 (4)	0.3182 (3)	1.0620 (2)	0.0279 (6)
H22A	0.4323	0.3597	1.0025	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0368 (12)	0.0373 (12)	0.0328 (11)	0.0141 (10)	0.0145 (10)	0.0116 (9)
O2	0.0349 (13)	0.0401 (13)	0.0535 (15)	0.0122 (10)	0.0215 (11)	0.0171 (11)
O3	0.0352 (12)	0.0365 (12)	0.0347 (12)	0.0114 (10)	0.0163 (10)	0.0116 (10)
O4	0.0688 (18)	0.0461 (15)	0.0451 (14)	0.0304 (14)	0.0230 (13)	0.0126 (12)
O5	0.0525 (15)	0.0504 (15)	0.0315 (12)	0.0159 (12)	0.0094 (11)	0.0155 (11)
O6	0.0388 (12)	0.0276 (11)	0.0331 (11)	0.0059 (9)	0.0210 (10)	0.0018 (9)
O7	0.0409 (12)	0.0249 (12)	0.0371 (12)	0.0039 (9)	0.0185 (10)	0.0001 (9)
O8	0.0381 (12)	0.0240 (11)	0.0351 (11)	0.0082 (9)	0.0217 (10)	0.0060 (9)
O9	0.110 (3)	0.081 (2)	0.102 (3)	0.070 (2)	0.078 (2)	0.0417 (19)
O10	0.0583 (16)	0.0476 (15)	0.0417 (14)	0.0040 (12)	0.0308 (13)	−0.0023 (11)
N1	0.0335 (14)	0.0357 (15)	0.0321 (14)	0.0068 (12)	0.0105 (12)	0.0111 (12)
N2	0.0466 (17)	0.0318 (15)	0.0512 (18)	0.0068 (13)	0.0302 (15)	0.0010 (13)
C1	0.0275 (15)	0.0283 (15)	0.0332 (16)	0.0083 (12)	0.0135 (13)	0.0064 (13)
C2	0.0259 (15)	0.0261 (15)	0.0294 (15)	0.0060 (12)	0.0114 (12)	0.0056 (12)
C3	0.0328 (16)	0.0361 (17)	0.0366 (17)	0.0152 (14)	0.0180 (14)	0.0077 (14)
C4	0.0333 (17)	0.050 (2)	0.0390 (18)	0.0189 (16)	0.0137 (15)	0.0152 (16)
C5	0.0319 (16)	0.047 (2)	0.0261 (15)	0.0045 (15)	0.0105 (13)	0.0049 (14)
C6	0.0306 (16)	0.0287 (16)	0.0349 (16)	0.0022 (13)	0.0182 (14)	0.0026 (13)
C7	0.0425 (18)	0.0285 (16)	0.0299 (16)	0.0112 (14)	0.0127 (14)	0.0058 (13)
C8	0.0357 (17)	0.0294 (16)	0.0235 (14)	0.0092 (13)	0.0087 (13)	0.0034 (12)
C9	0.0308 (15)	0.0265 (15)	0.0260 (14)	0.0053 (12)	0.0076 (12)	0.0051 (12)
C10	0.0377 (17)	0.0299 (16)	0.0229 (14)	0.0059 (13)	0.0103 (13)	0.0022 (12)
C11	0.0341 (16)	0.0290 (16)	0.0280 (15)	0.0048 (13)	0.0106 (13)	0.0017 (12)
C12	0.0284 (15)	0.0261 (15)	0.0265 (15)	0.0031 (12)	0.0059 (12)	0.0051 (12)
C13	0.0312 (16)	0.0350 (17)	0.0256 (15)	0.0014 (13)	0.0108 (13)	0.0068 (13)
C14	0.0279 (15)	0.0330 (17)	0.0302 (15)	0.0047 (13)	0.0113 (13)	0.0041 (13)
C15	0.0449 (19)	0.0300 (17)	0.0402 (18)	0.0003 (14)	0.0262 (16)	0.0001 (14)
C16	0.0280 (15)	0.0261 (16)	0.0242 (14)	0.0051 (12)	0.0085 (12)	0.0025 (12)
C17	0.0284 (15)	0.0236 (14)	0.0251 (14)	0.0046 (12)	0.0112 (12)	−0.0005 (11)
C18	0.0316 (16)	0.0245 (15)	0.0301 (15)	0.0077 (12)	0.0118 (13)	0.0067 (12)
C19	0.0314 (16)	0.0290 (16)	0.0276 (15)	0.0038 (13)	0.0132 (13)	0.0067 (12)
C20	0.0299 (15)	0.0250 (15)	0.0330 (16)	0.0028 (12)	0.0164 (13)	−0.0021 (12)
C21	0.0288 (15)	0.0277 (16)	0.0362 (17)	0.0088 (13)	0.0097 (13)	0.0032 (13)
C22	0.0300 (15)	0.0277 (15)	0.0229 (14)	0.0067 (12)	0.0063 (12)	0.0037 (12)

Geometric parameters (Å, º) top

O1—C8	1.324 (4)	C5—H5A	0.950
O1—C7	1.472 (4)	C6—C15	1.494 (4)
O2—C8	1.195 (4)	C7—H7A	0.990
O3—C8	1.362 (3)	C7—H7B	0.990
O3—C9	1.404 (3)	C9—C10	1.379 (4)
O4—N1	1.227 (3)	C9—C14	1.385 (4)
O5—N1	1.225 (3)	C10—C11	1.385 (4)
O6—C16	1.323 (3)	C10—H10A	0.950
O6—C15	1.467 (3)	C11—C12	1.377 (4)
O7—C16	1.199 (3)	C11—H11A	0.950
O8—C16	1.355 (3)	C12—C13	1.382 (4)
O8—C17	1.400 (3)	C13—C14	1.382 (4)
O9—N2	1.219 (4)	C13—H13A	0.950
O10—N2	1.220 (4)	C14—H14A	0.950
N1—C12	1.468 (4)	C15—H15A	0.990
N2—C20	1.471 (4)	C15—H15B	0.990
C1—C2	1.391 (4)	C17—C18	1.380 (4)
C1—C6	1.394 (4)	C17—C22	1.383 (4)
C1—H1A	0.950	C18—C19	1.386 (4)
C2—C3	1.392 (4)	C18—H18A	0.950
C2—C7	1.501 (4)	C19—C20	1.379 (4)
C3—C4	1.384 (4)	C19—H19A	0.950
C3—H3A	0.950	C20—C21	1.378 (4)
C4—C5	1.381 (4)	C21—C22	1.389 (4)
C4—H4A	0.950	C21—H21A	0.950
C5—C6	1.390 (4)	C22—H22A	0.950

C8—O1—C7	116.3 (2)	C9—C10—H10A	120.7
C8—O3—C9	119.8 (2)	C11—C10—H10A	120.7
C16—O6—C15	114.3 (2)	C12—C11—C10	118.7 (3)
C16—O8—C17	118.4 (2)	C12—C11—H11A	120.7
O5—N1—O4	123.6 (3)	C10—C11—H11A	120.7
O5—N1—C12	117.9 (3)	C11—C12—C13	122.9 (3)
O4—N1—C12	118.5 (2)	C11—C12—N1	118.5 (3)
O9—N2—O10	123.2 (3)	C13—C12—N1	118.6 (3)
O9—N2—C20	118.2 (3)	C12—C13—C14	118.4 (3)
O10—N2—C20	118.6 (3)	C12—C13—H13A	120.8
C2—C1—C6	121.0 (3)	C14—C13—H13A	120.8
C2—C1—H1A	119.5	C13—C14—C9	118.8 (3)
C6—C1—H1A	119.5	C13—C14—H14A	120.6
C1—C2—C3	119.2 (3)	C9—C14—H14A	120.6
C1—C2—C7	121.4 (3)	O6—C15—C6	106.4 (2)
C3—C2—C7	119.3 (3)	O6—C15—H15A	110.4
C4—C3—C2	119.9 (3)	C6—C15—H15A	110.4
C4—C3—H3A	120.0	O6—C15—H15B	110.4
C2—C3—H3A	120.0	C6—C15—H15B	110.4
C5—C4—C3	120.6 (3)	H15A—C15—H15B	108.6
C5—C4—H4A	119.7	O7—C16—O6	128.0 (3)
C3—C4—H4A	119.7	O7—C16—O8	126.2 (3)
C4—C5—C6	120.4 (3)	O6—C16—O8	105.7 (2)
C4—C5—H5A	119.8	C18—C17—C22	122.3 (3)
C6—C5—H5A	119.8	C18—C17—O8	116.0 (2)
C5—C6—C1	118.8 (3)	C22—C17—O8	121.6 (2)
C5—C6—C15	120.2 (3)	C17—C18—C19	119.2 (3)
C1—C6—C15	120.9 (3)	C17—C18—H18A	120.4
O1—C7—C2	110.4 (2)	C19—C18—H18A	120.4
O1—C7—H7A	109.6	C20—C19—C18	118.0 (3)
C2—C7—H7A	109.6	C20—C19—H19A	121.0
O1—C7—H7B	109.6	C18—C19—H19A	121.0
C2—C7—H7B	109.6	C21—C20—C19	123.2 (3)
H7A—C7—H7B	108.1	C21—C20—N2	118.6 (3)
O2—C8—O1	128.1 (3)	C19—C20—N2	118.2 (3)
O2—C8—O3	126.4 (3)	C20—C21—C22	118.5 (3)
O1—C8—O3	105.5 (2)	C20—C21—H21A	120.8
C10—C9—C14	122.6 (3)	C22—C21—H21A	120.8
C10—C9—O3	122.7 (3)	C17—C22—C21	118.6 (3)
C14—C9—O3	114.6 (3)	C17—C22—H22A	120.7
C9—C10—C11	118.5 (3)	C21—C22—H22A	120.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O10ⁱ	0.95	2.55	3.134 (4)	120
C15—H15B···O9ⁱ	0.99	2.58	3.504 (4)	155
C21—H21A···O7ⁱ	0.95	2.50	3.264 (3)	138

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₂O₁₀
M_r	468.37
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.5956 (4), 9.2367 (5), 14.1550 (8)
α, β, γ (°)	94.094 (2), 107.134 (3), 105.674 (3)
V (Å³)	1020.00 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.34 × 0.20 × 0.20

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.808, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	10107, 4580, 3182
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.166, 1.15
No. of reflections	4580
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.26

Computer programs: COLLECT (Nonius, 2002), DENZO–SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O10ⁱ	0.95	2.55	3.134 (4)	120
C15—H15B···O9ⁱ	0.99	2.58	3.504 (4)	155
C21—H21A···O7ⁱ	0.95	2.50	3.264 (3)	138

Symmetry code: (i) −x+1, −y+1, −z+2.

Acknowledgements

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

References

Nawazish Ali, S., Begum, S., Winnik, M. A. & Lough, A. J. (2008). Acta Cryst. E64, o281. Web of Science CrossRef IUCr Journals Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar