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Acta Cryst. (2011). E67, o1130    [ doi:10.1107/S1600536811013158 ]

Methyl 3,4-bis(cyclopropylmethoxy)benzoate

X.-C. Cheng, J.-J. Hou, C.-Z. Xie, R.-L. Wang and W.-R. Xu

Abstract top

The title compound, C16H20O4, was obtained unintentionally as the byproduct of an attempted synthesis of methyl 3-(cyclopropylmethoxy)-4-hydroxybenzoate. In the crystal, the molecules are linked by intermolecular C-H...O interactions.

Comment top

Roflumilast is an effective phosphodiesterase-4 inhibitor (PDE4 inhibitor), which can be used in the treatment of asthma, inflammation, bronchitis, allergy and other disorders related to immune system, heart and kidney. During the development of our own PDE4 inhibitors, roflumilast was synthesized as the positive control in the bioactivity screening, and the title compound,methyl 3,4-bis(cyclopropylmethoxy)benzoate, was a byproduct during preparation of the intermediate methyl 3-(cyclopropylmethoxy)-4-hydroxybenzoate.The crystallographic analysis of the title compound is done to confirm the chemical structure of the title compound. In the title compound, all bond lengths and angles are normal and in a good agreement with those reported previously (Hou, et al., 2010). In the crystal structure, the hydroxy groups are involved in the formation of intermolecular C—H···O hydrogen bonds(Tab 1), which link the molecules related by translation along axis b into one-dimensional chains.

Related literature top

For the preparation, see: Bose et al. (2005). For a similar structure, see: Hou et al. (2010).

Experimental top

A mixture of 3,4-dihydroxy methyl benzoate (1.68 g, 10 mmol) and potassium carbonate (2.76 g, 20 mmol) in acetone (50 ml) was added with a solution of cyclopropyl methyl bromide (1.35 g, 10 mmol) in acetone (50 ml). The reaction mixture was stirred at 40 °C for 18 h, and then was filtered. The filtrate was evaporated on a rotary evaporator to get the dried solid, which was then purified by flash column chromatography to obtain methyl 3-(cyclopropylmethoxy)-4-hydroxybenzoate, methyl 4-(cyclopropylmethoxy)-3-hydroxybenzoate, and the title compound methyl 3,4-bis(cyclopropylmethoxy)benzoate(Bose,et al.,2005).

Crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in ethyl acetate/n-hexane (1/10 by volume).

Refinement top

H atoms were positioned geometrically (C—H = 0.95–1.00 Å) and refined as riding, with Uiso(H) = 1.2 Ueq of the parent atom.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure (Rigaku, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids, and H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. The packing of the title compound, showing the one-dimensional structure,with intermolecular hydrogen bonds (dashed lines); for clarity H atoms have been omitted.
Methyl 3,4-bis(cyclopropylmethoxy)benzoate top
Crystal data top
C16H20O4F(000) = 592.00
Mr = 276.33Dx = 1.278 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2abCell parameters from 6064 reflections
a = 4.9018 (8) Åθ = 1.3–31.4°
b = 15.543 (2) ŵ = 0.09 mm−1
c = 18.846 (2) ÅT = 113 K
V = 1435.9 (3) Å3Prism, colorless
Z = 40.22 × 0.20 × 0.18 mm
Data collection top
Rigaku Saturn724 CCD
diffractometer		3300 reflections with F2 > 2.0σ(F2)
Detector resolution: 14.222 pixels mm-1Rint = 0.034
ω scansθmax = 29.1°
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		h = −6→6
Tmin = 0.891, Tmax = 0.984k = −21→21
20068 measured reflectionsl = −25→25
3852 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0778P)2]
where P = (Fo2 + 2Fc2)/3
3852 reflections(Δ/σ)max = 0.001
182 parametersΔρmax = 0.57 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods
Crystal data top
C16H20O4V = 1435.9 (3) Å3
Mr = 276.33Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.9018 (8) ŵ = 0.09 mm−1
b = 15.543 (2) ÅT = 113 K
c = 18.846 (2) Å0.22 × 0.20 × 0.18 mm
Data collection top
Rigaku Saturn724 CCD
diffractometer		3852 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)		3300 reflections with F2 > 2.0σ(F2)
Tmin = 0.891, Tmax = 0.984Rint = 0.034
20068 measured reflectionsθmax = 29.1°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.114Δρmax = 0.57 e Å−3
S = 1.06Δρmin = −0.19 e Å−3
3852 reflectionsAbsolute structure: ?
182 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O(1)0.3872 (2)0.69719 (7)0.66936 (5)0.0321
O(2)0.6968 (2)0.59026 (7)0.66908 (5)0.0306
O(3)0.7825 (2)0.48335 (5)0.42141 (5)0.0209
O(4)0.4320 (2)0.56811 (6)0.34625 (4)0.0250
C(1)0.4862 (3)0.62225 (8)0.56094 (7)0.0192
C(2)0.6558 (3)0.56094 (8)0.52884 (7)0.0184
C(3)0.6319 (3)0.54351 (8)0.45719 (6)0.0174
C(4)0.4378 (3)0.58918 (8)0.41612 (7)0.0193
C(5)0.2695 (3)0.64967 (8)0.44863 (7)0.0213
C(6)0.2930 (3)0.66574 (8)0.52102 (7)0.0211
C(7)0.5139 (3)0.64194 (8)0.63788 (7)0.0216
C(8)0.7487 (4)0.60502 (11)0.74361 (7)0.0406
C(9)0.9395 (3)0.42507 (8)0.46452 (6)0.0199
C(10)1.0118 (3)0.34763 (8)0.42075 (7)0.0205
C(11)1.2662 (3)0.29938 (9)0.44212 (8)0.0262
C(12)1.2614 (3)0.35005 (9)0.37423 (7)0.0246
C(13)0.2283 (3)0.61039 (9)0.30217 (7)0.0302
C(14)0.2718 (4)0.57919 (10)0.22787 (7)0.0330
C(15)0.5052 (4)0.61632 (12)0.18752 (10)0.0442
C(16)0.2225 (4)0.64137 (13)0.16830 (8)0.0428
H(2)0.78780.53120.55650.022*
H(5)0.13810.68000.42130.026*
H(6)0.17650.70660.54310.025*
H(8A)0.57500.60780.76930.049*
H(8B)0.84690.65950.74950.049*
H(8C)0.85930.55780.76260.049*
H(9A)0.83190.40730.50650.024*
H(9B)1.10780.45380.48130.024*
H(10)0.85580.31200.40330.025*
H(11A)1.37470.32250.48210.031*
H(11B)1.26330.23580.43860.031*
H(12A)1.25580.31760.32910.030*
H(12B)1.36710.40430.37250.030*
H(13A)0.25040.67360.30450.036*
H(13B)0.04230.59550.31860.036*
H(14)0.22710.51750.21830.040*
H(15A)0.62010.65970.21180.053*
H(15B)0.60470.57790.15460.053*
H(16A)0.14620.61840.12350.051*
H(16B)0.16150.70020.18070.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O(1)0.03980.03110.02530.00800.0001−0.0084
O(2)0.03910.03480.01790.0103−0.0046−0.0070
O(3)0.02510.02070.01700.0073−0.00110.0001
O(4)0.03460.02320.01700.0084−0.00410.0008
C(1)0.02050.01760.0194−0.00200.0025−0.0008
C(2)0.01710.01870.0194−0.0004−0.0002−0.0003
C(3)0.01920.01520.01780.00060.0017−0.0000
C(4)0.02280.01820.0170−0.0013−0.00170.0020
C(5)0.02220.01880.02290.0010−0.00140.0024
C(6)0.02130.01850.02350.00120.0042−0.0012
C(7)0.02430.01970.0208−0.00310.0009−0.0025
C(8)0.05750.04410.02020.0155−0.0122−0.0113
C(9)0.02130.02050.01790.0038−0.00040.0030
C(10)0.01890.02030.02220.00110.00090.0013
C(11)0.02510.02440.02910.00710.00260.0046
C(12)0.02470.02550.02360.00170.00600.0002
C(13)0.03370.03350.02350.0069−0.00520.0038
C(14)0.03890.03500.02510.0013−0.00490.0053
C(15)0.04570.04980.03710.00280.00380.0098
C(16)0.05100.05420.02300.0148−0.00430.0114
Geometric parameters (Å, °) top
O(1)—C(7)1.2143 (17)C(15)—C(16)1.484 (3)
O(2)—C(7)1.3397 (11)C(2)—H(2)0.950
O(2)—C(8)1.4458 (19)C(5)—H(5)0.950
O(3)—C(3)1.3692 (14)C(6)—H(6)0.950
O(3)—C(9)1.4397 (10)C(8)—H(8A)0.980
O(4)—C(4)1.3572 (17)C(8)—H(8B)0.980
O(4)—C(13)1.4558 (13)C(8)—H(8C)0.980
C(1)—C(2)1.4017 (18)C(9)—H(9A)0.990
C(1)—C(6)1.3856 (15)C(9)—H(9B)0.990
C(1)—C(7)1.488 (3)C(10)—H(10)1.000
C(2)—C(3)1.382 (3)C(11)—H(11A)0.990
C(3)—C(4)1.4169 (14)C(11)—H(11B)0.990
C(4)—C(5)1.3930 (18)C(12)—H(12A)0.990
C(5)—C(6)1.392 (3)C(12)—H(12B)0.990
C(9)—C(10)1.502 (2)C(13)—H(13A)0.990
C(10)—C(11)1.5098 (14)C(13)—H(13B)0.990
C(10)—C(12)1.506 (2)C(14)—H(14)1.000
C(11)—C(12)1.5026 (17)C(15)—H(15A)0.990
C(13)—C(14)1.497 (3)C(15)—H(15B)0.990
C(14)—C(15)1.490 (3)C(16)—H(16A)0.990
C(14)—C(16)1.5009 (15)C(16)—H(16B)0.990
O(1)···C(6)2.875 (2)H(6)···C(1)viii3.4340
O(1)···C(8)2.6738 (14)H(6)···C(2)iv3.4221
O(2)···C(2)2.6895 (19)H(6)···C(4)viii3.4694
O(3)···O(4)2.5873 (12)H(6)···C(5)viii2.9995
O(3)···C(12)3.2546 (14)H(6)···C(6)viii2.9886
O(4)···C(15)3.1046 (16)H(6)···H(2)iv3.3350
C(1)···C(4)2.787 (3)H(6)···H(5)viii3.2433
C(2)···C(5)2.7880 (15)H(6)···H(5)i2.9456
C(2)···C(9)2.804 (2)H(6)···H(6)viii3.2354
C(3)···C(6)2.7955 (18)H(6)···H(6)i3.2354
C(5)···C(13)2.834 (3)H(8A)···O(3)ii3.2735
O(1)···C(13)i3.468 (4)H(8A)···C(10)ii2.9685
O(2)···C(15)ii3.545 (2)H(8A)···C(12)ii2.6574
O(3)···C(5)iii3.556 (2)H(8A)···C(14)ix3.4558
O(3)···C(12)iv3.407 (2)H(8A)···H(8C)iv3.5954
O(4)···C(12)iv3.5306 (19)H(8A)···H(10)ii2.8381
C(2)···C(6)iii3.526 (3)H(8A)···H(12A)ii2.2901
C(3)···C(5)iii3.538 (3)H(8A)···H(12B)ii2.9188
C(5)···O(3)iv3.556 (3)H(8A)···H(12B)v3.3617
C(5)···C(3)iv3.538 (3)H(8A)···H(13B)ix3.3436
C(6)···C(2)iv3.526 (3)H(8A)···H(14)ix2.6278
C(8)···C(12)ii3.578 (3)H(8A)···H(16B)i3.1585
C(8)···C(12)v3.509 (7)H(8B)···O(1)iii3.1047
C(12)···O(3)iii3.407 (4)H(8B)···C(12)v3.0389
C(12)···O(4)iii3.531 (3)H(8B)···C(16)i3.5151
C(12)···C(8)vi3.578 (5)H(8B)···H(10)ii3.0967
C(12)···C(8)vii3.509 (5)H(8B)···H(12A)ii3.3323
C(13)···O(1)viii3.468 (3)H(8B)···H(12A)v2.4836
C(15)···O(2)vi3.545 (3)H(8B)···H(12B)v2.8849
C(15)···C(16)iii3.556 (4)H(8B)···H(13A)i2.8266
C(16)···C(15)iv3.556 (3)H(8B)···H(14)ii3.5027
O(1)···H(6)2.5982H(8B)···H(15A)i3.1979
O(1)···H(8A)2.5145H(8B)···H(16B)i2.7043
O(1)···H(8B)2.7752H(8C)···O(3)ii3.1385
O(2)···H(2)2.3550H(8C)···O(4)ii2.7133
O(3)···H(2)2.6517H(8C)···C(12)v3.1519
O(3)···H(10)2.7092H(8C)···C(13)ii3.3878
O(3)···H(12B)3.2512H(8C)···C(14)ii2.8694
O(4)···H(5)2.6652H(8C)···C(15)ii3.1254
O(4)···H(14)2.7276H(8C)···H(8A)iii3.5954
O(4)···H(15A)3.0496H(8C)···H(10)ii3.4987
C(1)···H(5)3.2624H(8C)···H(12A)v2.9798
C(2)···H(6)3.2736H(8C)···H(12B)v2.5373
C(2)···H(9A)2.5735H(8C)···H(13B)ix3.2663
C(2)···H(9B)2.9122H(8C)···H(14)ix3.2138
C(3)···H(5)3.2890H(8C)···H(14)ii2.4852
C(3)···H(9A)2.5109H(8C)···H(15A)ii3.5154
C(3)···H(9B)2.7551H(8C)···H(15B)ii2.9371
C(4)···H(2)3.2784H(9A)···C(11)iv3.4606
C(4)···H(6)3.2707H(9A)···C(11)x3.3711
C(4)···H(13A)2.6440H(9A)···C(15)ii3.5231
C(4)···H(13B)2.6731H(9A)···H(11A)iv2.6402
C(5)···H(13A)2.7429H(9A)···H(11A)x3.5855
C(5)···H(13B)2.8201H(9A)···H(11B)x2.4769
C(6)···H(2)3.2707H(9A)···H(12B)iv3.4008
C(7)···H(2)2.6681H(9A)···H(15B)ii2.8173
C(7)···H(6)2.6334H(9A)···H(16A)ix3.2426
C(7)···H(8A)2.5499H(9A)···H(16A)ii3.4014
C(7)···H(8B)2.6766H(9B)···O(3)iii3.5250
C(7)···H(8C)3.1783H(9B)···O(4)iii3.4870
C(9)···H(2)2.5055H(9B)···C(1)iii3.5419
C(9)···H(11A)2.6830H(9B)···C(2)iii3.2847
C(9)···H(11B)3.3775H(9B)···C(3)iii2.9578
C(9)···H(12A)3.4221H(9B)···C(4)iii2.9243
C(9)···H(12B)2.7392H(9B)···C(5)iii3.2049
C(11)···H(9A)2.9697H(9B)···C(6)iii3.4973
C(11)···H(9B)2.6293H(9B)···H(15B)ii3.4627
C(12)···H(9A)3.3820H(9B)···H(16A)ii3.1460
C(12)···H(9B)2.6912H(10)···C(8)vi3.3147
C(13)···H(5)2.5315H(10)···C(11)iv2.9874
C(13)···H(15A)2.6793H(10)···C(11)x3.4165
C(13)···H(15B)3.3759H(10)···C(12)iv3.0231
C(13)···H(16A)3.3933H(10)···C(16)xi3.0002
C(13)···H(16B)2.7007H(10)···H(8A)vi2.8381
C(15)···H(13A)2.6862H(10)···H(8B)vi3.0967
C(15)···H(13B)3.3697H(10)···H(8C)vi3.4987
C(16)···H(13A)2.6193H(10)···H(11A)iv2.7913
C(16)···H(13B)3.0514H(10)···H(11A)x3.0070
H(2)···H(9A)2.1545H(10)···H(11B)iv3.2057
H(2)···H(9B)2.4315H(10)···H(11B)x3.1032
H(5)···H(6)2.3396H(10)···H(12A)iv3.2582
H(5)···H(13A)2.2709H(10)···H(12B)iv2.8516
H(5)···H(13B)2.3861H(10)···H(16A)xi3.0514
H(9A)···H(10)2.4474H(10)···H(16B)xi2.3527
H(9A)···H(11A)3.0045H(11A)···O(3)iii3.3990
H(9B)···H(10)2.9237H(11A)···C(9)iii3.2119
H(9B)···H(11A)2.4243H(11A)···C(10)iii3.3530
H(9B)···H(11B)3.5652H(11A)···C(10)xii3.2863
H(9B)···H(12B)2.5324H(11A)···C(11)xii3.0519
H(10)···H(11A)2.9497H(11A)···C(16)ii3.5854
H(10)···H(11B)2.4153H(11A)···H(9A)iii2.6402
H(10)···H(12A)2.4108H(11A)···H(9A)xii3.5855
H(10)···H(12B)2.9459H(11A)···H(10)iii2.7913
H(11A)···H(12A)2.9435H(11A)···H(10)xii3.0070
H(11A)···H(12B)2.4248H(11A)···H(11A)x3.3981
H(11B)···H(12A)2.4247H(11A)···H(11A)xii3.3981
H(11B)···H(12B)2.9436H(11A)···H(11B)x3.4694
H(13A)···H(14)2.9227H(11A)···H(11B)xii2.5855
H(13A)···H(15A)2.5272H(11A)···H(16A)ii2.8206
H(13A)···H(16A)3.5547H(11B)···C(9)xii3.2146
H(13A)···H(16B)2.4089H(11B)···C(10)xii3.1923
H(13B)···H(14)2.4211H(11B)···C(11)x3.3599
H(13B)···H(16B)3.1209H(11B)···C(11)xii3.3805
H(14)···H(15A)2.9345H(11B)···C(15)xiii3.2233
H(14)···H(15B)2.3983H(11B)···C(16)xi3.4476
H(14)···H(16A)2.4103H(11B)···C(16)xiii3.5454
H(14)···H(16B)2.9445H(11B)···H(9A)xii2.4769
H(15A)···H(16A)2.9283H(11B)···H(10)iii3.2057
H(15A)···H(16B)2.4063H(11B)···H(10)xii3.1032
H(15B)···H(16A)2.4063H(11B)···H(11A)x2.5855
H(15B)···H(16B)2.9283H(11B)···H(11A)xii3.4694
O(1)···H(5)i2.8414H(11B)···H(11B)x3.3990
O(1)···H(8B)iv3.1047H(11B)···H(11B)xii3.3990
O(1)···H(12A)ii3.0988H(11B)···H(15A)xiii3.1240
O(1)···H(13A)i2.7280H(11B)···H(15B)xiii3.0867
O(1)···H(13B)i3.3183H(11B)···H(16A)xi2.9551
O(1)···H(14)ix3.5071H(11B)···H(16B)xi3.1149
O(1)···H(15A)viii3.4180H(12A)···O(1)vi3.0988
O(1)···H(16B)i3.5118H(12A)···C(8)vi3.1867
O(2)···H(14)ix2.8256H(12A)···C(8)vii3.1528
O(2)···H(14)ii3.4119H(12A)···C(15)xiii3.3551
O(2)···H(15B)ii2.8026H(12A)···H(8A)vi2.2901
O(3)···H(5)iii3.5191H(12A)···H(8B)vi3.3323
O(3)···H(8A)vi3.2735H(12A)···H(8B)vii2.4836
O(3)···H(8C)vi3.1385H(12A)···H(8C)vii2.9798
O(3)···H(9B)iv3.5250H(12A)···H(10)iii3.2582
O(3)···H(11A)iv3.3990H(12A)···H(15A)xiii2.6428
O(3)···H(12B)iv2.5506H(12A)···H(16B)xi2.7473
O(3)···H(13B)iii2.9009H(12A)···H(16B)xiii3.3943
O(4)···H(8C)vi2.7133H(12B)···O(3)iii2.5506
O(4)···H(9B)iv3.4870H(12B)···O(4)iii2.6136
O(4)···H(12B)iv2.6136H(12B)···C(3)iii2.9854
O(4)···H(13B)iii3.0664H(12B)···C(4)iii3.0090
C(1)···H(5)i3.1796H(12B)···C(8)vii3.0774
C(1)···H(6)i3.4340H(12B)···C(9)iii3.3140
C(1)···H(9B)iv3.5419H(12B)···C(10)iii3.4040
C(2)···H(6)iii3.4221H(12B)···C(13)iii3.5333
C(2)···H(9B)iv3.2847H(12B)···H(8A)vi2.9188
C(2)···H(15B)ii3.4133H(12B)···H(8A)vii3.3617
C(3)···H(5)iii3.3346H(12B)···H(8B)vii2.8849
C(3)···H(9B)iv2.9578H(12B)···H(8C)vii2.5373
C(3)···H(12B)iv2.9854H(12B)···H(9A)iii3.4008
C(3)···H(13B)iii3.3947H(12B)···H(10)iii2.8516
C(4)···H(6)i3.4694H(12B)···H(13B)iii3.5216
C(4)···H(9B)iv2.9243H(12B)···H(14)iii3.4659
C(4)···H(12B)iv3.0090H(13A)···O(1)viii2.7280
C(4)···H(13B)iii3.4883H(13A)···C(7)viii3.2771
C(5)···H(6)i2.9995H(13A)···C(8)viii3.5579
C(5)···H(9B)iv3.2049H(13A)···H(8B)viii2.8266
C(6)···H(2)iv3.3092H(13A)···H(15A)iv3.5566
C(6)···H(5)i3.1287H(13B)···O(1)viii3.3183
C(6)···H(6)i2.9886H(13B)···O(3)iv2.9009
C(6)···H(9B)iv3.4973H(13B)···O(4)iv3.0664
C(7)···H(5)i3.0449H(13B)···C(3)iv3.3947
C(7)···H(13A)i3.2771H(13B)···C(4)iv3.4883
C(7)···H(14)ix3.1360H(13B)···H(8A)xiv3.3436
C(8)···H(10)ii3.3147H(13B)···H(8C)xiv3.2663
C(8)···H(12A)ii3.1867H(13B)···H(12B)iv3.5216
C(8)···H(12A)v3.1528H(13B)···H(15A)iv3.0552
C(8)···H(12B)v3.0774H(14)···O(1)xiv3.5071
C(8)···H(13A)i3.5579H(14)···O(2)xiv2.8256
C(8)···H(14)ix3.0483H(14)···O(2)vi3.4119
C(8)···H(14)ii3.2335H(14)···C(7)xiv3.1360
C(8)···H(15B)ii3.3790H(14)···C(8)xiv3.0483
C(8)···H(16B)i3.3736H(14)···C(8)vi3.2335
C(9)···H(11A)iv3.2119H(14)···H(8A)xiv2.6278
C(9)···H(11B)x3.2146H(14)···H(8B)vi3.5027
C(9)···H(12B)iv3.3140H(14)···H(8C)xiv3.2138
C(9)···H(15B)ii3.5885H(14)···H(8C)vi2.4852
C(10)···H(8A)vi2.9685H(14)···H(12B)iv3.4659
C(10)···H(11A)iv3.3530H(14)···H(15B)iv3.4109
C(10)···H(11A)x3.2863H(15A)···O(1)i3.4180
C(10)···H(11B)x3.1923H(15A)···C(12)xv3.4231
C(10)···H(12B)iv3.4040H(15A)···C(13)iii3.5184
C(10)···H(16B)xi3.1033H(15A)···C(14)iii3.4443
C(11)···H(9A)iii3.4606H(15A)···C(16)iii3.0775
C(11)···H(9A)xii3.3711H(15A)···H(8B)viii3.1979
C(11)···H(10)iii2.9874H(15A)···H(8C)vi3.5154
C(11)···H(10)xii3.4165H(15A)···H(11B)xv3.1240
C(11)···H(11A)x3.0519H(15A)···H(12A)xv2.6428
C(11)···H(11B)x3.3805H(15A)···H(13A)iii3.5566
C(11)···H(11B)xii3.3599H(15A)···H(13B)iii3.0552
C(11)···H(16B)xi3.4832H(15A)···H(16A)iii3.1351
C(12)···H(8A)vi2.6574H(15A)···H(16B)iii2.7897
C(12)···H(8B)vii3.0389H(15B)···O(2)vi2.8026
C(12)···H(8C)vii3.1519H(15B)···C(2)vi3.4133
C(12)···H(10)iii3.0231H(15B)···C(8)vi3.3790
C(12)···H(15A)xiii3.4231H(15B)···C(9)vi3.5885
C(12)···H(16B)xi3.2856H(15B)···C(14)iii3.5496
C(13)···H(8C)vi3.3878H(15B)···C(16)iii3.1951
C(13)···H(12B)iv3.5333H(15B)···H(2)vi2.5642
C(13)···H(15A)iv3.5184H(15B)···H(8C)vi2.9371
C(14)···H(8A)xiv3.4558H(15B)···H(9A)vi2.8173
C(14)···H(8C)vi2.8694H(15B)···H(9B)vi3.4627
C(14)···H(15A)iv3.4443H(15B)···H(11B)xv3.0867
C(14)···H(15B)iv3.5496H(15B)···H(14)iii3.4109
C(15)···H(2)vi3.5201H(15B)···H(16A)iii2.7897
C(15)···H(8C)vi3.1254H(15B)···H(16B)iii3.3623
C(15)···H(9A)vi3.5231H(16A)···C(15)iv3.3656
C(15)···H(11B)xv3.2233H(16A)···H(2)xiv3.3954
C(15)···H(12A)xv3.3551H(16A)···H(9A)xiv3.2426
C(15)···H(16A)iii3.3656H(16A)···H(9A)vi3.4014
C(15)···H(16B)iii3.4736H(16A)···H(9B)vi3.1460
C(16)···H(8B)viii3.5151H(16A)···H(10)xvi3.0514
C(16)···H(10)xvi3.0002H(16A)···H(11A)vi2.8206
C(16)···H(11A)vi3.5854H(16A)···H(11B)xvi2.9551
C(16)···H(11B)xvi3.4476H(16A)···H(15A)iv3.1351
C(16)···H(11B)xv3.5454H(16A)···H(15B)iv2.7897
C(16)···H(15A)iv3.0775H(16B)···O(1)viii3.5118
C(16)···H(15B)iv3.1951H(16B)···C(8)viii3.3736
H(2)···C(6)iii3.3092H(16B)···C(10)xvi3.1033
H(2)···C(15)ii3.5201H(16B)···C(11)xvi3.4832
H(2)···H(6)iii3.3350H(16B)···C(12)xvi3.2856
H(2)···H(15B)ii2.5642H(16B)···C(15)iv3.4736
H(2)···H(16A)ix3.3954H(16B)···H(8A)viii3.1585
H(5)···O(1)viii2.8414H(16B)···H(8B)viii2.7043
H(5)···O(3)iv3.5191H(16B)···H(10)xvi2.3527
H(5)···C(1)viii3.1796H(16B)···H(11B)xvi3.1149
H(5)···C(3)iv3.3346H(16B)···H(12A)xvi2.7473
H(5)···C(6)viii3.1287H(16B)···H(12A)xv3.3943
H(5)···C(7)viii3.0449H(16B)···H(15A)iv2.7897
H(5)···H(6)viii2.9456H(16B)···H(15B)iv3.3623
H(5)···H(6)i3.2433
C(7)—O(2)—C(8)116.68 (12)H(8A)—C(8)—H(8B)109.475
C(3)—O(3)—C(9)116.11 (9)H(8A)—C(8)—H(8C)109.468
C(4)—O(4)—C(13)117.33 (10)H(8B)—C(8)—H(8C)109.472
C(2)—C(1)—C(6)120.17 (12)O(3)—C(9)—H(9A)109.948
C(2)—C(1)—C(7)120.42 (11)O(3)—C(9)—H(9B)109.953
C(6)—C(1)—C(7)119.40 (11)C(10)—C(9)—H(9A)109.961
C(1)—C(2)—C(3)120.30 (12)C(10)—C(9)—H(9B)109.956
O(3)—C(3)—C(2)124.69 (11)H(9A)—C(9)—H(9B)108.328
O(3)—C(3)—C(4)115.80 (10)C(9)—C(10)—H(10)116.366
C(2)—C(3)—C(4)119.50 (11)C(11)—C(10)—H(10)116.367
O(4)—C(4)—C(3)115.03 (11)C(12)—C(10)—H(10)116.375
O(4)—C(4)—C(5)125.26 (12)C(10)—C(11)—H(11A)117.777
C(3)—C(4)—C(5)119.71 (12)C(10)—C(11)—H(11B)117.773
C(4)—C(5)—C(6)120.21 (12)C(12)—C(11)—H(11A)117.769
C(1)—C(6)—C(5)120.09 (12)C(12)—C(11)—H(11B)117.772
O(1)—C(7)—O(2)123.48 (12)H(11A)—C(11)—H(11B)114.909
O(1)—C(7)—C(1)125.10 (12)C(10)—C(12)—H(12A)117.744
O(2)—C(7)—C(1)111.42 (11)C(10)—C(12)—H(12B)117.746
O(3)—C(9)—C(10)108.69 (9)C(11)—C(12)—H(12A)117.745
C(9)—C(10)—C(11)116.52 (11)C(11)—C(12)—H(12B)117.747
C(9)—C(10)—C(12)119.44 (11)H(12A)—C(12)—H(12B)114.871
C(11)—C(10)—C(12)59.78 (9)O(4)—C(13)—H(13A)110.344
C(10)—C(11)—C(12)59.97 (9)O(4)—C(13)—H(13B)110.344
C(10)—C(12)—C(11)60.25 (9)C(14)—C(13)—H(13A)110.360
O(4)—C(13)—C(14)106.85 (12)C(14)—C(13)—H(13B)110.358
C(13)—C(14)—C(15)117.46 (14)H(13A)—C(13)—H(13B)108.585
C(13)—C(14)—C(16)117.91 (14)C(13)—C(14)—H(14)116.594
C(15)—C(14)—C(16)59.51 (12)C(15)—C(14)—H(14)116.598
C(14)—C(15)—C(16)60.61 (12)C(16)—C(14)—H(14)116.603
C(14)—C(16)—C(15)59.89 (12)C(14)—C(15)—H(15A)117.706
C(1)—C(2)—H(2)119.856C(14)—C(15)—H(15B)117.711
C(3)—C(2)—H(2)119.846C(16)—C(15)—H(15A)117.702
C(4)—C(5)—H(5)119.900C(16)—C(15)—H(15B)117.720
C(6)—C(5)—H(5)119.892H(15A)—C(15)—H(15B)114.826
C(1)—C(6)—H(6)119.947C(14)—C(16)—H(16A)117.785
C(5)—C(6)—H(6)119.960C(14)—C(16)—H(16B)117.794
O(2)—C(8)—H(8A)109.469C(15)—C(16)—H(16A)117.781
O(2)—C(8)—H(8B)109.474C(15)—C(16)—H(16B)117.788
O(2)—C(8)—H(8C)109.470H(16A)—C(16)—H(16B)114.905
C(8)—O(2)—C(7)—O(1)−2.4 (2)C(2)—C(3)—C(4)—O(4)179.31 (11)
C(8)—O(2)—C(7)—C(1)177.99 (12)C(2)—C(3)—C(4)—C(5)−1.41 (19)
C(3)—O(3)—C(9)—C(10)160.99 (10)O(4)—C(4)—C(5)—C(6)179.71 (12)
C(9)—O(3)—C(3)—C(2)11.35 (17)C(3)—C(4)—C(5)—C(6)0.52 (20)
C(9)—O(3)—C(3)—C(4)−167.98 (11)C(4)—C(5)—C(6)—C(1)0.69 (20)
C(4)—O(4)—C(13)—C(14)177.72 (12)O(3)—C(9)—C(10)—C(11)153.94 (11)
C(13)—O(4)—C(4)—C(3)177.39 (11)O(3)—C(9)—C(10)—C(12)85.31 (14)
C(13)—O(4)—C(4)—C(5)−1.83 (19)C(9)—C(10)—C(11)—C(12)−110.19 (13)
C(2)—C(1)—C(6)—C(5)−1.01 (19)C(9)—C(10)—C(12)—C(11)105.34 (13)
C(6)—C(1)—C(2)—C(3)0.09 (19)C(11)—C(10)—C(12)—C(11)0.0
C(2)—C(1)—C(7)—O(1)175.66 (13)C(12)—C(10)—C(11)—C(12)0.0
C(2)—C(1)—C(7)—O(2)−4.76 (17)C(10)—C(11)—C(12)—C(10)0.0
C(7)—C(1)—C(2)—C(3)−179.24 (12)O(4)—C(13)—C(14)—C(15)−76.77 (16)
C(6)—C(1)—C(7)—O(1)−3.7 (2)O(4)—C(13)—C(14)—C(16)−144.94 (14)
C(6)—C(1)—C(7)—O(2)175.90 (12)C(13)—C(14)—C(15)—C(16)−107.83 (16)
C(7)—C(1)—C(6)—C(5)178.33 (12)C(13)—C(14)—C(16)—C(15)107.08 (17)
C(1)—C(2)—C(3)—O(3)−178.20 (12)C(15)—C(14)—C(16)—C(15)0.0
C(1)—C(2)—C(3)—C(4)1.11 (19)C(16)—C(14)—C(15)—C(16)0.0
O(3)—C(3)—C(4)—O(4)−1.31 (17)C(14)—C(15)—C(16)—C(14)0.0
O(3)—C(3)—C(4)—C(5)177.96 (11)
Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+3/2, −y+1, z+1/2; (iii) x+1, y, z; (iv) x−1, y, z; (v) −x+5/2, −y+1, z+1/2; (vi) −x+3/2, −y+1, z−1/2; (vii) −x+5/2, −y+1, z−1/2; (viii) x−1/2, −y+3/2, −z+1; (ix) −x+1/2, −y+1, z+1/2; (x) x−1/2, −y+1/2, −z+1; (xi) −x+1, y−1/2, −z+1/2; (xii) x+1/2, −y+1/2, −z+1; (xiii) −x+2, y−1/2, −z+1/2; (xiv) −x+1/2, −y+1, z−1/2; (xv) −x+2, y+1/2, −z+1/2; (xvi) −x+1, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O3iii0.992.553.4073 (18)145
Symmetry codes: (iii) x+1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O3i0.992.553.4073 (18)145
Symmetry codes: (i) x+1, y, z.
Acknowledgements top

This research was supported by the Tianjin Medical University Science Foundation (2009ky16) and a China Postdoctoral Science Foundation funded project (20100480655).

references
References top

Bose, P., Sachdeva, Y. P., Rathore, R. S. & Kumar, Y. (2005). WO Patent 2005/026095 A1.

Hou, J.-J., Cheng, X.-C., Wang, R.-L. & Wang, S.-Q. (2010). Acta Cryst. E66, o2004.

Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.

Rigaku. (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.