organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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 (Aeq) positions of the chair-form cyclo­hexane ring while in the other mol­ecule the substitution is axial (Bax). 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 Aeq and 11.7 (2)° for Bax. In Bax, 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[Ali, S. N., Begum, S., Winnik, S. A. & Lough, A. J. (2008). Acta Cryst. E64, o281.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N2O10

  • Mr = 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[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.768, Tmax = 0.996

  • 7088 measured reflections

  • 3355 independent reflections

  • 1633 reflections with I > 2σ(I)

  • Rint = 0.080

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.190

  • S = 0.96

  • 3355 reflections

  • 289 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[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.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2001[Sheldrick, G. M. (2001). SHELXTL/PC. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL/PC.

Supporting information


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.

Refinement top

The H atoms were placed in calculated positions, with C—H = 0.95–1.00 Å, and refined as riding, with Uiso(H) = 1.2Ueq(C).

Structure description 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.

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
[Figure 1] 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).
[Figure 2] 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
C20H18N2O10Z = 2
Mr = 446.36F(000) = 464
Triclinic, P1Dx = 1.521 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6804 (14) ÅCell parameters from 7088 reflections
b = 11.6548 (18) Åθ = 2.7–25.2°
c = 12.3092 (11) ŵ = 0.12 mm1
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 tube1633 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
Detector resolution: 9 pixels mm-1θmax = 25.2°, θmin = 2.7°
φ scans and ω scans with κ offsetsh = 99
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1213
Tmin = 0.768, Tmax = 0.996l = 1414
7088 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0923P)2]
where P = (Fo2 + 2Fc2)/3
3355 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C20H18N2O10γ = 82.310 (7)°
Mr = 446.36V = 974.6 (3) Å3
Triclinic, P1Z = 2
a = 7.6804 (14) ÅMo Kα radiation
b = 11.6548 (18) ŵ = 0.12 mm1
c = 12.3092 (11) ÅT = 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)
Tmin = 0.768, Tmax = 0.996Rint = 0.080
7088 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.190H-atom parameters constrained
S = 0.96Δρmax = 0.30 e Å3
3355 reflectionsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
O1A0.1429 (4)0.0985 (3)0.2676 (2)0.0517 (8)
O2A0.4182 (4)0.0092 (3)0.2921 (2)0.0504 (8)
O3A0.3173 (4)0.1684 (3)0.1182 (2)0.0524 (8)
O4A0.9007 (4)0.1716 (3)0.2527 (3)0.0685 (10)
O5A1.0631 (5)0.1300 (3)0.0977 (3)0.0690 (10)
N1A0.9198 (6)0.1542 (3)0.1481 (4)0.0498 (10)
C1A0.1660 (6)0.0576 (4)0.5216 (3)0.0495 (12)
H1A10.12450.15090.55020.059*
H1A20.29600.04630.52110.059*
C2A0.1003 (6)0.0194 (4)0.3939 (3)0.0513 (12)
H2A10.13890.01450.33960.062*
H2A20.15200.11120.36240.062*
C3A0.0979 (6)0.0112 (4)0.3927 (3)0.0474 (12)
H3A0.15180.07960.41450.057*
C4A0.3057 (6)0.0763 (4)0.2341 (4)0.0453 (11)
C5A0.4739 (6)0.1635 (4)0.0559 (3)0.0409 (11)
C6A0.6345 (6)0.1517 (4)0.1054 (4)0.0476 (12)
H6AA0.64420.14590.18440.057*
C7A0.7824 (6)0.1483 (4)0.0383 (4)0.0478 (11)
H7AA0.89620.13810.07090.057*
C8A0.7621 (6)0.1599 (4)0.0766 (3)0.0402 (10)
C9A0.6019 (6)0.1746 (4)0.1267 (3)0.0459 (11)
H9AA0.59260.18310.20680.055*
C10A0.4527 (6)0.1771 (4)0.0601 (3)0.0455 (11)
H10A0.33910.18780.09320.055*
O1B0.9940 (4)0.5357 (3)0.1688 (2)0.0493 (8)
O2B0.9203 (4)0.3799 (3)0.3498 (2)0.0568 (9)
O3B0.8673 (4)0.5951 (3)0.2963 (2)0.0486 (8)
O4B0.4719 (5)0.5191 (3)0.7792 (3)0.0708 (11)
O5B0.4665 (5)0.7279 (4)0.6849 (3)0.0731 (11)
N1B0.5072 (5)0.6198 (4)0.6918 (3)0.0527 (10)
C1B0.8165 (6)0.4921 (4)0.0214 (4)0.0507 (12)
H1B10.73250.45090.04650.061*
H1B20.74800.55650.00080.061*
C2B0.9217 (6)0.3884 (4)0.0905 (3)0.0500 (12)
H2B10.84090.35350.15970.060*
H2B20.97300.31620.07280.060*
C3B1.0669 (6)0.4393 (4)0.1269 (3)0.0497 (12)
H3B1.13920.36590.19380.060*
C4B0.9251 (6)0.4897 (4)0.2793 (4)0.0474 (11)
C5B0.7791 (6)0.5888 (4)0.4005 (3)0.0425 (11)
C6B0.7732 (6)0.4775 (4)0.5097 (3)0.0457 (11)
H6BA0.82990.39600.51890.055*
C7B0.6813 (6)0.4894 (4)0.6054 (4)0.0473 (11)
H7BA0.67350.41490.68100.057*
C8B0.6022 (6)0.6085 (4)0.5905 (3)0.0412 (10)
C9B0.6109 (6)0.7178 (4)0.4819 (3)0.0439 (11)
H9BA0.55540.79960.47270.053*
C10B0.7007 (6)0.7072 (4)0.3872 (3)0.0405 (10)
H10B0.70850.78220.31200.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.052 (2)0.0532 (18)0.0391 (16)0.0002 (15)0.0040 (14)0.0132 (14)
O2A0.052 (2)0.0445 (17)0.0441 (16)0.0074 (16)0.0042 (15)0.0133 (13)
O3A0.055 (2)0.0517 (17)0.0347 (16)0.0048 (15)0.0035 (14)0.0093 (14)
O4A0.061 (3)0.087 (2)0.072 (2)0.0174 (19)0.0189 (18)0.048 (2)
O5A0.045 (2)0.064 (2)0.078 (2)0.0100 (18)0.0049 (19)0.0146 (17)
N1A0.047 (3)0.040 (2)0.059 (3)0.0088 (19)0.004 (2)0.0180 (18)
C1A0.051 (3)0.052 (3)0.045 (2)0.015 (2)0.003 (2)0.019 (2)
C2A0.056 (3)0.062 (3)0.039 (2)0.008 (2)0.001 (2)0.025 (2)
C3A0.055 (3)0.051 (3)0.036 (2)0.007 (2)0.001 (2)0.019 (2)
C4A0.049 (3)0.046 (3)0.044 (3)0.006 (2)0.008 (2)0.025 (2)
C5A0.043 (3)0.035 (2)0.041 (2)0.003 (2)0.010 (2)0.0155 (18)
C6A0.055 (3)0.048 (3)0.042 (2)0.003 (2)0.007 (2)0.022 (2)
C7A0.043 (3)0.048 (3)0.052 (3)0.007 (2)0.005 (2)0.021 (2)
C8A0.042 (3)0.032 (2)0.044 (2)0.0007 (19)0.002 (2)0.0166 (18)
C9A0.054 (3)0.045 (2)0.035 (2)0.010 (2)0.001 (2)0.0141 (19)
C10A0.040 (3)0.050 (3)0.039 (2)0.008 (2)0.000 (2)0.0126 (19)
O1B0.059 (2)0.0453 (16)0.0435 (17)0.0044 (15)0.0073 (14)0.0209 (13)
O2B0.079 (3)0.0435 (19)0.0430 (17)0.0046 (16)0.0087 (15)0.0169 (15)
O3B0.063 (2)0.0411 (17)0.0404 (16)0.0016 (15)0.0082 (14)0.0194 (13)
O4B0.077 (3)0.075 (2)0.0455 (19)0.004 (2)0.0170 (17)0.0174 (17)
O5B0.084 (3)0.072 (2)0.079 (2)0.009 (2)0.0228 (19)0.050 (2)
N1B0.048 (3)0.064 (3)0.048 (2)0.003 (2)0.0061 (18)0.029 (2)
C1B0.051 (3)0.049 (3)0.054 (3)0.002 (2)0.005 (2)0.027 (2)
C2B0.066 (3)0.045 (3)0.042 (2)0.009 (2)0.009 (2)0.022 (2)
C3B0.066 (3)0.042 (2)0.042 (2)0.003 (2)0.004 (2)0.021 (2)
C4B0.060 (3)0.043 (3)0.036 (2)0.008 (2)0.001 (2)0.014 (2)
C5B0.046 (3)0.047 (3)0.035 (2)0.007 (2)0.0012 (19)0.0187 (19)
C6B0.048 (3)0.039 (2)0.051 (3)0.002 (2)0.000 (2)0.022 (2)
C7B0.048 (3)0.047 (3)0.041 (2)0.008 (2)0.001 (2)0.015 (2)
C8B0.038 (3)0.046 (3)0.040 (2)0.005 (2)0.0024 (19)0.020 (2)
C9B0.043 (3)0.043 (2)0.050 (3)0.003 (2)0.003 (2)0.025 (2)
C10B0.045 (3)0.041 (2)0.037 (2)0.010 (2)0.0005 (19)0.0180 (19)
Geometric parameters (Å, º) top
O1A—C4A1.327 (5)O1B—C4B1.328 (5)
O1A—C3A1.469 (4)O1B—C3B1.472 (5)
O2A—C4A1.199 (5)O2B—C4B1.184 (5)
O3A—C4A1.352 (5)O3B—C4B1.352 (5)
O3A—C5A1.404 (5)O3B—C5B1.398 (5)
O4A—N1A1.223 (4)O4B—N1B1.236 (4)
O5A—N1A1.224 (5)O5B—N1B1.222 (5)
N1A—C8A1.475 (5)N1B—C8B1.463 (5)
C1A—C2A1.518 (5)C1B—C3Bii1.507 (5)
C1A—C3Ai1.525 (6)C1B—C2B1.535 (5)
C1A—H1A10.9900C1B—H1B10.9900
C1A—H1A20.9900C1B—H1B20.9900
C2A—C3A1.512 (6)C2B—C3B1.503 (6)
C2A—H2A10.9900C2B—H2B10.9900
C2A—H2A20.9900C2B—H2B20.9900
C3A—C1Ai1.525 (6)C3B—C1Bii1.507 (5)
C3A—H3A1.0000C3B—H3B1.0000
C5A—C6A1.365 (6)C5B—C10B1.370 (5)
C5A—C10A1.379 (6)C5B—C6B1.388 (5)
C6A—C7A1.379 (6)C6B—C7B1.395 (6)
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.373 (5)C7B—C8B1.373 (6)
C7A—H7AA0.9500C7B—H7BA0.9500
C8A—C9A1.358 (6)C8B—C9B1.375 (5)
C9A—C10A1.381 (6)C9B—C10B1.372 (5)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—H10A0.9500C10B—H10B0.9500
C4A—O1A—C3A116.0 (3)C4B—O1B—C3B116.4 (3)
C4A—O3A—C5A118.0 (3)C4B—O3B—C5B123.4 (3)
O4A—N1A—O5A123.8 (4)O5B—N1B—O4B123.8 (4)
O4A—N1A—C8A118.7 (4)O5B—N1B—C8B118.3 (4)
O5A—N1A—C8A117.5 (4)O4B—N1B—C8B117.8 (4)
C2A—C1A—C3Ai109.7 (3)C3Bii—C1B—C2B112.3 (4)
C2A—C1A—H1A1109.7C3Bii—C1B—H1B1109.1
C3Ai—C1A—H1A1109.7C2B—C1B—H1B1109.1
C2A—C1A—H1A2109.7C3Bii—C1B—H1B2109.1
C3Ai—C1A—H1A2109.7C2B—C1B—H1B2109.1
H1A1—C1A—H1A2108.2H1B1—C1B—H1B2107.9
C3A—C2A—C1A111.1 (3)C3B—C2B—C1B112.9 (4)
C3A—C2A—H2A1109.4C3B—C2B—H2B1109.0
C1A—C2A—H2A1109.4C1B—C2B—H2B1109.0
C3A—C2A—H2A2109.4C3B—C2B—H2B2109.0
C1A—C2A—H2A2109.4C1B—C2B—H2B2109.0
H2A1—C2A—H2A2108.0H2B1—C2B—H2B2107.8
O1A—C3A—C2A105.7 (3)O1B—C3B—C2B110.5 (4)
O1A—C3A—C1Ai108.5 (3)O1B—C3B—C1Bii106.1 (3)
C2A—C3A—C1Ai111.9 (4)C2B—C3B—C1Bii111.9 (3)
O1A—C3A—H3A110.2O1B—C3B—H3B109.4
C2A—C3A—H3A110.2C2B—C3B—H3B109.4
C1Ai—C3A—H3A110.2C1Bii—C3B—H3B109.4
O2A—C4A—O1A127.8 (4)O2B—C4B—O1B127.6 (4)
O2A—C4A—O3A126.7 (4)O2B—C4B—O3B127.0 (4)
O1A—C4A—O3A105.5 (4)O1B—C4B—O3B105.3 (3)
C6A—C5A—C10A122.8 (4)C10B—C5B—C6B121.5 (4)
C6A—C5A—O3A122.0 (4)C10B—C5B—O3B113.0 (3)
C10A—C5A—O3A115.1 (4)C6B—C5B—O3B125.5 (4)
C5A—C6A—C7A118.6 (4)C5B—C6B—C7B117.8 (4)
C5A—C6A—H6AA120.7C5B—C6B—H6BA121.1
C7A—C6A—H6AA120.7C7B—C6B—H6BA121.1
C8A—C7A—C6A118.8 (4)C8B—C7B—C6B120.1 (4)
C8A—C7A—H7AA120.6C8B—C7B—H7BA120.0
C6A—C7A—H7AA120.6C6B—C7B—H7BA120.0
C9A—C8A—C7A122.5 (4)C7B—C8B—C9B121.2 (4)
C9A—C8A—N1A118.4 (4)C7B—C8B—N1B119.6 (3)
C7A—C8A—N1A119.0 (4)C9B—C8B—N1B119.2 (4)
C8A—C9A—C10A119.3 (4)C10B—C9B—C8B119.2 (4)
C8A—C9A—H9AA120.3C10B—C9B—H9BA120.4
C10A—C9A—H9AA120.3C8B—C9B—H9BA120.4
C5A—C10A—C9A117.9 (4)C5B—C10B—C9B120.2 (3)
C5A—C10A—H10A121.0C5B—C10B—H10B119.9
C9A—C10A—H10A121.0C9B—C10B—H10B119.9
Symmetry codes: (i) x, y, z+1; (ii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10A—H10A···O5Aiii0.952.323.205 (6)155
C6B—H6BA···O2B0.952.242.812 (5)118
C9B—H9BA···O2Aiv0.952.483.184 (5)131
Symmetry codes: (iii) x1, y, z; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC20H18N2O10
Mr446.36
Crystal system, space groupTriclinic, 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)
V3)974.6 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.22 × 0.20 × 0.08
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.768, 0.996
No. of measured, independent and
observed [I > 2σ(I)] reflections
7088, 3355, 1633
Rint0.080
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.190, 0.96
No. of reflections3355
No. of parameters289
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C10A—H10A···O5Ai0.952.323.205 (6)155
C6B—H6BA···O2B0.952.242.812 (5)118
C9B—H9BA···O2Aii0.952.483.184 (5)131
Symmetry codes: (i) x1, 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

First citationAli, S. N., Begum, S., Winnik, S. A. & Lough, A. J. (2008). Acta Cryst. E64, o281.  Web of Science CrossRef IUCr Journals Google Scholar
First citationAltomare, 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
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationNonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, 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
First citationSheldrick, G. M. (2001). SHELXTL/PC. Version 6.1. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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