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Acta Cryst. (2011). E67, o270    [ doi:10.1107/S1600536810053730 ]

2-{[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfanyl}-1H-benzimidazole monohydrate

G.-B. Ren, M.-H. Hong, J.-L. Zhong, D.-X. Yi and L.-H. Xu

Abstract top

The asymmetric unit of the title compound, C16H14F3N3OS·H2O, contains two independent molecules (A and B) and two water molecules, one of which is disordered over two positions in a 0.790 (8):0.210 (8) ratio. The molecular conformations are close, the benzimidazole mean plane and pyridine ring forming dihedral angles of 1.8 (3) and 0.1 (2)° in molecules A and B, respectively. The water molecules are involved in formation of two independent hydrogen-bonded chains via N-H...O and O-H...N hydrogen bonds. Chains propagating along the a axis are formed by molecule A and one independent water molecule, while chains propagating along the b axis are formed by molecule B and the other independent water molecule. The crystal packing exhibits [pi]-[pi] interactions, as indicated by short distances of 3.607 (3) and 3.701 (3) Å between the centroids of the imidazole and pyridine rings of neighbouring molecules.

Comment top

The title compound, (I), is important intermediate in the synthesis of lansoprazole (Del Rio et al., 2007; Reddy et al., 2008), which exhibits anti-ulcer effect (Iwahi et al.,1991). Herewith we present its crystal structure.

The asymmetric unit of (I) contains two independent molecules (Fig. 1), A and B, respectively, and two crystalline water molecules, one of which is disordered over two positions in a ratio 0.790 (8):0.210 (8). The molecular conformations of A and B are close - the benzimidazole mean plane and pyridine ring form the dihedral angles of 1.8 (3)° and 0.1 (2)° in A and B, respectively. The bond lengths and angles in A and B are normal and comparable with those observed in the related compounds (Swamy et al., 2007; Hakim,et al., 2010). The torsion angle of C7—S1—C8—C9 in A is 178.85 (12) ° (179.88 (14) ° in B).

The crystalline water molecules are involved in formation of two independent hydrogen-bonded chains via N—H···O and O—H···N hydrogen bonds (Table 1). The chains propagating along the axis a are formed by the molecule A and one independent water molecule, while the chains propagating along the axis b are formed by the molecule B and another independent water molecule. The crystal packing exhibits π-π interactions proved by short distances of 3.607 (3) and 3.701 (3) Å between the centroids of imidazole and pyridine rings from the neighbouring molecules.

Related literature top

The title compound is an intermediate in the synthesis of the anti-ulcer drug lansoprazole [systematic name (RS)-2-([3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl)-1H-benzo[d]imidazole], see: Del Rio et al. (2007); Reddy et al. (2008); Iwahi et al. (1991). For related structrues, see: Swamy et al. (2007); Hakim Al-arique et al. (2010).

Experimental top

The raw material was kindly provided by Shanghai Enran Sci-Tech Investment Management Co., Ltd.The compound was dissolved in acetonitrile and suitable crystals of X-ray were obtained by slow evaporation at room temperature over a period of one week.

Refinement top

Water H atoms were initially located in a difference Fourier map (O—H 0.80-0.85 Å), and refined as riding, with Uiso(H) = 1.5 Ueq(O). All other H atoms were constrained to an ideal geometry (C—H 0.93 - 0.97 Å; N—H 0.86 Å). All H atoms were refined as riding, with and Uiso(H) = 1.2 - 1.5 Ueq of the parent atom. One water molecule (OB) has been treated as disordered between two positions with the occupancies refined to 0.790 (8) and 0.210 (8), respectively.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The content of asymmetric unit (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines denote hydrogen bonds. Only major component of the disordered water molecule is shown. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A packing diagram.
2-{[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfanyl}- 1H-benzimidazole monohydrate top
Crystal data top
C16H14F3N3OS·H2OZ = 4
Mr = 371.39F(000) = 768
Triclinic, P1Dx = 1.467 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 7.3526 (1) ÅCell parameters from 9679 reflections
b = 7.4702 (1) Åθ = 5.8–67.1°
c = 30.6500 (3) ŵ = 2.15 mm−1
α = 88.27°T = 296 K
β = 87.79°Prism, colourless
γ = 89.13°0.28 × 0.12 × 0.10 mm
V = 1681.27 (4) Å3
Data collection top
Bruker SMART APEX
diffractometer		5282 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.017
graphiteθmax = 67.4°, θmin = 4.3°
φ and ω scansh = −7→8
12461 measured reflectionsk = −8→8
5446 independent reflectionsl = −33→36
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0671P)2 + 0.6061P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5446 reflectionsΔρmax = 0.41 e Å−3
462 parametersΔρmin = −0.32 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0062 (5)
Crystal data top
C16H14F3N3OS·H2Oγ = 89.13°
Mr = 371.39V = 1681.27 (4) Å3
Triclinic, P1Z = 4
a = 7.3526 (1) ÅCu Kα radiation
b = 7.4702 (1) ŵ = 2.15 mm−1
c = 30.6500 (3) ÅT = 296 K
α = 88.27°0.28 × 0.12 × 0.10 mm
β = 87.79°
Data collection top
Bruker SMART APEX
diffractometer		5282 reflections with I > 2σ(I)
12461 measured reflectionsRint = 0.017
5446 independent reflectionsθmax = 67.4°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.117Δρmax = 0.41 e Å−3
S = 1.06Δρmin = −0.32 e Å−3
5446 reflectionsAbsolute structure: ?
462 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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*/UeqOcc. (<1)
S1A0.20282 (6)0.80754 (6)0.034292 (14)0.04220 (15)
F1A−0.4248 (3)0.4400 (3)−0.22095 (6)0.1133 (7)
F2A−0.5441 (2)0.6396 (2)−0.18024 (5)0.0767 (4)
F3A−0.5417 (2)0.3690 (2)−0.15787 (6)0.0898 (5)
O1A−0.28512 (19)0.57155 (19)−0.11848 (4)0.0499 (3)
N1A−0.0279 (2)0.8860 (2)0.10435 (5)0.0449 (4)
N2A0.2693 (2)0.9203 (2)0.11406 (5)0.0419 (3)
H2AA0.38470.91960.10830.050*
N3A0.1655 (2)0.6976 (2)−0.04904 (5)0.0480 (4)
C1A0.1826 (3)0.9679 (2)0.15275 (6)0.0414 (4)
C2A0.2464 (3)1.0248 (3)0.19196 (7)0.0516 (5)
H2AB0.37021.03470.19640.062*
C3A0.1170 (3)1.0661 (3)0.22414 (7)0.0593 (6)
H3AA0.15461.10590.25080.071*
C4A−0.0675 (3)1.0495 (3)0.21770 (7)0.0615 (6)
H4AA−0.15071.08060.23990.074*
C5A−0.1308 (3)0.9882 (3)0.17920 (7)0.0568 (5)
H5AA−0.25470.97510.17540.068*
C6A−0.0026 (3)0.9463 (2)0.14626 (6)0.0432 (4)
C7A0.1375 (2)0.8745 (2)0.08674 (6)0.0390 (4)
C8A−0.0216 (2)0.7654 (2)0.01491 (6)0.0407 (4)
H8AA−0.07980.67260.03310.049*
H8AB−0.09610.87340.01670.049*
C9A−0.0052 (2)0.7070 (2)−0.03177 (6)0.0384 (4)
C10A0.1846 (3)0.6412 (3)−0.08980 (7)0.0543 (5)
H10A0.30190.6321−0.10210.065*
C11A0.0431 (3)0.5958 (3)−0.11481 (6)0.0504 (5)
H11A0.06380.5563−0.14310.061*
C12A−0.1325 (3)0.6103 (2)−0.09671 (6)0.0415 (4)
C13A−0.1595 (2)0.6663 (2)−0.05382 (6)0.0388 (4)
C14A−0.2595 (3)0.5145 (3)−0.16192 (6)0.0495 (5)
H14A−0.19140.4023−0.16240.059*
H14B−0.19210.6033−0.17940.059*
C15A−0.4423 (4)0.4908 (3)−0.17966 (7)0.0618 (6)
C16A−0.3470 (3)0.6790 (3)−0.03280 (7)0.0491 (5)
H16A−0.33890.7198−0.00350.074*
H16B−0.40210.5632−0.03210.074*
H16C−0.41980.7621−0.04940.074*
OA0.6171 (2)0.9501 (2)0.07662 (6)0.0674 (4)
HA10.71280.90710.08670.101*
HA20.63921.04470.06300.101*
S1B0.26211 (7)0.81787 (6)0.488240 (15)0.04885 (16)
F1B0.0052 (3)1.4472 (3)0.75578 (5)0.1092 (7)
F2B0.1852 (3)1.5488 (2)0.70486 (6)0.0992 (6)
F3B−0.0976 (3)1.5730 (2)0.69808 (6)0.1053 (6)
O1B0.0650 (2)1.30722 (19)0.64771 (4)0.0576 (4)
N1B0.3484 (2)1.0373 (2)0.41683 (5)0.0485 (4)
N2B0.3662 (3)0.7438 (2)0.40584 (5)0.0506 (4)
H2BA0.36050.63050.41140.061*
N3B0.1553 (3)0.8612 (2)0.57285 (6)0.0578 (5)
C1B0.4148 (3)0.8255 (3)0.36638 (6)0.0479 (4)
C2B0.4657 (3)0.7591 (3)0.32581 (7)0.0604 (6)
H2BB0.47330.63670.32120.072*
C3B0.5043 (3)0.8839 (4)0.29259 (7)0.0652 (6)
H3BA0.53860.84440.26490.078*
C4B0.4932 (3)1.0663 (4)0.29952 (7)0.0648 (6)
H4BA0.52051.14630.27650.078*
C5B0.4428 (3)1.1314 (3)0.33978 (7)0.0605 (6)
H5BA0.43541.25400.34420.073*
C6B0.4032 (3)1.0091 (3)0.37361 (6)0.0480 (4)
C7B0.3289 (3)0.8765 (3)0.43438 (6)0.0443 (4)
C8B0.2354 (3)1.0420 (3)0.50903 (6)0.0473 (4)
H8BA0.34981.10470.50580.057*
H8BB0.14501.10880.49270.057*
C9B0.1760 (3)1.0277 (3)0.55651 (6)0.0461 (4)
C10B0.1024 (4)0.8433 (3)0.61464 (7)0.0637 (6)
H10B0.08670.72800.62630.076*
C11B0.0695 (3)0.9845 (3)0.64178 (7)0.0562 (5)
H11B0.03270.96570.67090.067*
C12B0.0929 (3)1.1550 (3)0.62422 (6)0.0479 (4)
C13B0.1465 (3)1.1813 (3)0.58049 (6)0.0458 (4)
C14B0.0293 (3)1.2837 (3)0.69304 (6)0.0558 (5)
H14C0.12161.20650.70580.067*
H14D−0.08841.22880.69860.067*
C15B0.0308 (4)1.4636 (4)0.71260 (8)0.0706 (7)
C16B0.1682 (4)1.3666 (3)0.56065 (7)0.0620 (6)
H16D0.14121.45350.58250.093*
H16E0.08611.38360.53720.093*
H16F0.29111.38110.54950.093*
OB0.4154 (6)0.3918 (3)0.43764 (9)0.0886 (14)0.790 (8)
OB'0.251 (2)0.3984 (11)0.4323 (3)0.090 (5)0.210 (8)
HB10.35860.29710.43390.134*0.790 (8)
HB1'0.33610.32610.43120.134*0.210 (8)
HB20.51390.35490.44550.134*0.790 (8)
HB2'0.15810.33750.42720.134*0.210 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0356 (3)0.0494 (3)0.0416 (3)−0.00072 (17)0.00079 (18)−0.00341 (18)
F1A0.0937 (13)0.179 (2)0.0719 (10)0.0062 (12)−0.0171 (9)−0.0662 (12)
F2A0.0676 (10)0.0855 (10)0.0770 (9)0.0115 (7)−0.0118 (7)0.0009 (7)
F3A0.0722 (11)0.0777 (10)0.1210 (14)−0.0239 (8)−0.0155 (9)−0.0013 (9)
O1A0.0464 (8)0.0642 (8)0.0394 (7)−0.0068 (6)0.0000 (6)−0.0081 (6)
N1A0.0361 (9)0.0526 (9)0.0458 (8)−0.0014 (6)−0.0003 (7)−0.0009 (7)
N2A0.0322 (8)0.0490 (8)0.0445 (8)−0.0006 (6)−0.0006 (6)−0.0029 (6)
N3A0.0378 (9)0.0584 (10)0.0476 (9)−0.0039 (7)0.0042 (7)−0.0056 (7)
C1A0.0427 (11)0.0390 (9)0.0423 (9)0.0002 (7)0.0001 (8)0.0014 (7)
C2A0.0512 (13)0.0535 (11)0.0506 (11)−0.0028 (9)−0.0058 (9)−0.0042 (9)
C3A0.0729 (16)0.0612 (13)0.0440 (11)−0.0026 (10)0.0011 (10)−0.0059 (9)
C4A0.0666 (16)0.0698 (14)0.0469 (11)0.0042 (11)0.0141 (10)−0.0032 (10)
C5A0.0449 (12)0.0698 (14)0.0547 (12)0.0005 (9)0.0086 (9)0.0013 (10)
C6A0.0416 (11)0.0453 (10)0.0424 (9)0.0005 (7)0.0013 (8)0.0016 (7)
C7A0.0359 (10)0.0379 (9)0.0431 (9)0.0007 (7)−0.0021 (7)0.0024 (7)
C8A0.0368 (10)0.0440 (9)0.0411 (9)−0.0010 (7)−0.0004 (7)−0.0010 (7)
C9A0.0375 (10)0.0368 (9)0.0404 (9)−0.0013 (7)0.0023 (7)0.0012 (7)
C10A0.0404 (11)0.0708 (13)0.0513 (11)−0.0056 (9)0.0109 (9)−0.0083 (9)
C11A0.0508 (12)0.0587 (12)0.0414 (10)−0.0043 (9)0.0089 (8)−0.0065 (8)
C12A0.0425 (11)0.0407 (9)0.0410 (9)−0.0049 (7)−0.0005 (8)0.0010 (7)
C13A0.0398 (10)0.0361 (9)0.0400 (9)−0.0011 (7)0.0036 (7)0.0010 (7)
C14A0.0578 (13)0.0492 (11)0.0416 (10)0.0000 (8)0.0010 (9)−0.0073 (8)
C15A0.0673 (15)0.0666 (14)0.0526 (12)0.0008 (11)−0.0056 (10)−0.0176 (10)
C16A0.0382 (11)0.0578 (11)0.0512 (11)−0.0022 (8)0.0025 (8)−0.0053 (9)
OA0.0362 (9)0.0880 (12)0.0770 (11)−0.0009 (7)0.0032 (7)0.0062 (9)
S1B0.0613 (3)0.0435 (3)0.0417 (3)−0.0018 (2)0.0023 (2)−0.00479 (19)
F1B0.184 (2)0.0958 (12)0.0464 (8)0.0074 (12)0.0272 (10)−0.0194 (8)
F2B0.1211 (15)0.0910 (12)0.0870 (11)−0.0297 (10)0.0105 (10)−0.0319 (9)
F3B0.1288 (16)0.0833 (11)0.1016 (13)0.0405 (11)0.0145 (11)−0.0096 (9)
O1B0.0808 (11)0.0539 (8)0.0378 (7)0.0024 (7)0.0050 (7)−0.0076 (6)
N1B0.0569 (10)0.0439 (9)0.0445 (8)0.0010 (7)0.0025 (7)−0.0065 (7)
N2B0.0636 (11)0.0399 (8)0.0485 (9)−0.0004 (7)0.0033 (8)−0.0091 (7)
N3B0.0814 (14)0.0469 (9)0.0449 (9)−0.0054 (8)0.0032 (9)−0.0030 (7)
C1B0.0470 (12)0.0527 (11)0.0443 (10)0.0000 (8)−0.0010 (8)−0.0089 (8)
C2B0.0628 (15)0.0654 (13)0.0539 (12)−0.0007 (10)0.0010 (10)−0.0197 (10)
C3B0.0583 (15)0.0947 (18)0.0430 (11)−0.0019 (12)0.0022 (10)−0.0127 (11)
C4B0.0622 (15)0.0843 (17)0.0470 (11)−0.0021 (11)0.0016 (10)0.0063 (11)
C5B0.0670 (15)0.0596 (13)0.0545 (12)−0.0006 (10)0.0006 (10)0.0029 (10)
C6B0.0473 (12)0.0528 (11)0.0438 (10)0.0017 (8)−0.0009 (8)−0.0043 (8)
C7B0.0458 (11)0.0443 (10)0.0430 (10)−0.0001 (7)−0.0016 (8)−0.0080 (8)
C8B0.0554 (12)0.0438 (10)0.0428 (10)−0.0037 (8)0.0031 (8)−0.0070 (8)
C9B0.0480 (12)0.0484 (10)0.0420 (10)−0.0038 (8)−0.0018 (8)−0.0031 (8)
C10B0.0935 (19)0.0489 (12)0.0483 (11)−0.0076 (11)0.0039 (11)0.0012 (9)
C11B0.0701 (15)0.0587 (12)0.0393 (10)−0.0053 (10)0.0018 (9)0.0002 (9)
C12B0.0508 (12)0.0532 (11)0.0404 (10)−0.0020 (8)−0.0022 (8)−0.0087 (8)
C13B0.0499 (12)0.0472 (10)0.0407 (9)−0.0037 (8)−0.0012 (8)−0.0037 (8)
C14B0.0641 (14)0.0643 (13)0.0386 (10)0.0024 (10)0.0058 (9)−0.0062 (9)
C15B0.092 (2)0.0712 (15)0.0477 (12)0.0052 (14)0.0155 (12)−0.0112 (11)
C16B0.0879 (18)0.0469 (11)0.0511 (12)−0.0078 (10)0.0046 (11)−0.0043 (9)
OB0.121 (4)0.0422 (11)0.1049 (19)−0.0115 (12)−0.0339 (17)0.0035 (11)
OB'0.119 (13)0.046 (4)0.103 (7)0.015 (5)0.006 (7)−0.008 (4)
Geometric parameters (Å, °) top
S1A—C7A1.7453 (18)F1B—C15B1.332 (3)
S1A—C8A1.8107 (18)F2B—C15B1.320 (3)
F1A—C15A1.333 (3)F3B—C15B1.321 (3)
F2A—C15A1.331 (3)O1B—C12B1.373 (2)
F3A—C15A1.324 (3)O1B—C14B1.410 (2)
O1A—C12A1.367 (2)N1B—C7B1.309 (3)
O1A—C14A1.415 (2)N1B—C6B1.391 (2)
N1A—C7A1.314 (2)N2B—C7B1.360 (2)
N1A—C6A1.394 (2)N2B—C1B1.375 (3)
N2A—C7A1.359 (2)N2B—H2BA0.8600
N2A—C1A1.379 (2)N3B—C10B1.328 (3)
N2A—H2AA0.8600N3B—C9B1.335 (3)
N3A—C10A1.332 (3)C1B—C2B1.388 (3)
N3A—C9A1.344 (2)C1B—C6B1.397 (3)
C1A—C2A1.387 (3)C2B—C3B1.384 (4)
C1A—C6A1.396 (3)C2B—H2BB0.9300
C2A—C3A1.382 (3)C3B—C4B1.386 (4)
C2A—H2AB0.9300C3B—H3BA0.9300
C3A—C4A1.386 (4)C4B—C5B1.376 (3)
C3A—H3AA0.9300C4B—H4BA0.9300
C4A—C5A1.378 (3)C5B—C6B1.386 (3)
C4A—H4AA0.9300C5B—H5BA0.9300
C5A—C6A1.393 (3)C8B—C9B1.504 (3)
C5A—H5AA0.9300C8B—H8BA0.9700
C8A—C9A1.508 (2)C8B—H8BB0.9700
C8A—H8AA0.9700C9B—C13B1.391 (3)
C8A—H8AB0.9700C10B—C11B1.376 (3)
C9A—C13A1.385 (3)C10B—H10B0.9300
C10A—C11A1.369 (3)C11B—C12B1.378 (3)
C10A—H10A0.9300C11B—H11B0.9300
C11A—C12A1.389 (3)C12B—C13B1.391 (3)
C11A—H11A0.9300C13B—C16B1.504 (3)
C12A—C13A1.398 (3)C14B—C15B1.488 (3)
C13A—C16A1.502 (3)C14B—H14C0.9700
C14A—C15A1.485 (3)C14B—H14D0.9700
C14A—H14A0.9700C16B—H16D0.9600
C14A—H14B0.9700C16B—H16E0.9600
C16A—H16A0.9600C16B—H16F0.9600
C16A—H16B0.9600OB—HB10.8399
C16A—H16C0.9600OB—HB1'0.8013
OA—HA10.8349OB—HB20.8132
OA—HA20.8249OB'—HB11.0873
S1B—C7B1.7490 (19)OB'—HB1'0.8201
S1B—C8B1.8146 (19)OB'—HB2'0.8488
C7A—S1A—C8A98.11 (8)C7B—N2B—C1B106.89 (16)
C12A—O1A—C14A117.06 (15)C7B—N2B—H2BA126.6
C7A—N1A—C6A104.30 (16)C1B—N2B—H2BA126.6
C7A—N2A—C1A106.86 (15)C10B—N3B—C9B117.15 (18)
C7A—N2A—H2AA126.6N2B—C1B—C2B132.8 (2)
C1A—N2A—H2AA126.6N2B—C1B—C6B105.28 (16)
C10A—N3A—C9A116.71 (17)C2B—C1B—C6B122.0 (2)
N2A—C1A—C2A132.64 (19)C3B—C2B—C1B116.8 (2)
N2A—C1A—C6A105.19 (16)C3B—C2B—H2BB121.6
C2A—C1A—C6A122.17 (18)C1B—C2B—H2BB121.6
C3A—C2A—C1A116.8 (2)C2B—C3B—C4B121.6 (2)
C3A—C2A—H2AB121.6C2B—C3B—H3BA119.2
C1A—C2A—H2AB121.6C4B—C3B—H3BA119.2
C2A—C3A—C4A121.6 (2)C5B—C4B—C3B121.4 (2)
C2A—C3A—H3AA119.2C5B—C4B—H4BA119.3
C4A—C3A—H3AA119.2C3B—C4B—H4BA119.3
C5A—C4A—C3A121.7 (2)C4B—C5B—C6B118.1 (2)
C5A—C4A—H4AA119.2C4B—C5B—H5BA120.9
C3A—C4A—H4AA119.2C6B—C5B—H5BA120.9
C4A—C5A—C6A117.7 (2)C5B—C6B—N1B130.08 (19)
C4A—C5A—H5AA121.2C5B—C6B—C1B120.15 (19)
C6A—C5A—H5AA121.2N1B—C6B—C1B109.77 (17)
C5A—C6A—N1A129.8 (2)N1B—C7B—N2B113.33 (17)
C5A—C6A—C1A120.08 (19)N1B—C7B—S1B127.96 (14)
N1A—C6A—C1A110.09 (16)N2B—C7B—S1B118.72 (14)
N1A—C7A—N2A113.55 (16)C9B—C8B—S1B108.66 (13)
N1A—C7A—S1A127.99 (14)C9B—C8B—H8BA110.0
N2A—C7A—S1A118.46 (13)S1B—C8B—H8BA110.0
C9A—C8A—S1A109.41 (12)C9B—C8B—H8BB110.0
C9A—C8A—H8AA109.8S1B—C8B—H8BB110.0
S1A—C8A—H8AA109.8H8BA—C8B—H8BB108.3
C9A—C8A—H8AB109.8N3B—C9B—C13B124.19 (18)
S1A—C8A—H8AB109.8N3B—C9B—C8B115.44 (17)
H8AA—C8A—H8AB108.2C13B—C9B—C8B120.37 (17)
N3A—C9A—C13A124.41 (16)N3B—C10B—C11B124.2 (2)
N3A—C9A—C8A115.40 (16)N3B—C10B—H10B117.9
C13A—C9A—C8A120.19 (15)C11B—C10B—H10B117.9
N3A—C10A—C11A124.36 (18)C10B—C11B—C12B117.57 (19)
N3A—C10A—H10A117.8C10B—C11B—H11B121.2
C11A—C10A—H10A117.8C12B—C11B—H11B121.2
C10A—C11A—C12A118.03 (18)O1B—C12B—C11B123.44 (18)
C10A—C11A—H11A121.0O1B—C12B—C13B115.97 (17)
C12A—C11A—H11A121.0C11B—C12B—C13B120.59 (18)
O1A—C12A—C11A123.68 (17)C9B—C13B—C12B116.33 (18)
O1A—C12A—C13A116.54 (16)C9B—C13B—C16B122.53 (18)
C11A—C12A—C13A119.78 (18)C12B—C13B—C16B121.12 (18)
C9A—C13A—C12A116.69 (16)O1B—C14B—C15B107.66 (18)
C9A—C13A—C16A122.08 (16)O1B—C14B—H14C110.2
C12A—C13A—C16A121.23 (17)C15B—C14B—H14C110.2
O1A—C14A—C15A107.55 (17)O1B—C14B—H14D110.2
O1A—C14A—H14A110.2C15B—C14B—H14D110.2
C15A—C14A—H14A110.2H14C—C14B—H14D108.5
O1A—C14A—H14B110.2F2B—C15B—F3B105.5 (2)
C15A—C14A—H14B110.2F2B—C15B—F1B107.3 (2)
H14A—C14A—H14B108.5F3B—C15B—F1B107.3 (2)
F3A—C15A—F2A105.6 (2)F2B—C15B—C14B113.3 (2)
F3A—C15A—F1A107.3 (2)F3B—C15B—C14B113.3 (2)
F2A—C15A—F1A106.2 (2)F1B—C15B—C14B109.8 (2)
F3A—C15A—C14A113.8 (2)C13B—C16B—H16D109.5
F2A—C15A—C14A113.79 (19)C13B—C16B—H16E109.5
F1A—C15A—C14A109.6 (2)H16D—C16B—H16E109.5
C13A—C16A—H16A109.5C13B—C16B—H16F109.5
C13A—C16A—H16B109.5H16D—C16B—H16F109.5
H16A—C16A—H16B109.5H16E—C16B—H16F109.5
C13A—C16A—H16C109.5HB1—OB—HB1'19.7
H16A—C16A—H16C109.5HB1—OB—HB2102.8
H16B—C16A—H16C109.5HB1'—OB—HB2122.4
HA1—OA—HA2109.7HB1—OB'—HB1'5.6
C7B—S1B—C8B98.24 (9)HB1—OB'—HB2'102.8
C12B—O1B—C14B116.91 (16)HB1'—OB'—HB2'104.6
C7B—N1B—C6B104.74 (16)
C7A—N2A—C1A—C2A179.6 (2)C7B—N2B—C1B—C2B−179.7 (2)
C7A—N2A—C1A—C6A0.33 (19)C7B—N2B—C1B—C6B−0.1 (2)
N2A—C1A—C2A—C3A178.4 (2)N2B—C1B—C2B—C3B179.3 (2)
C6A—C1A—C2A—C3A−2.4 (3)C6B—C1B—C2B—C3B−0.1 (3)
C1A—C2A—C3A—C4A0.7 (3)C1B—C2B—C3B—C4B0.1 (4)
C2A—C3A—C4A—C5A1.2 (4)C2B—C3B—C4B—C5B−0.2 (4)
C3A—C4A—C5A—C6A−1.3 (3)C3B—C4B—C5B—C6B0.1 (4)
C4A—C5A—C6A—N1A−178.5 (2)C4B—C5B—C6B—N1B−179.5 (2)
C4A—C5A—C6A—C1A−0.3 (3)C4B—C5B—C6B—C1B−0.1 (3)
C7A—N1A—C6A—C5A177.7 (2)C7B—N1B—C6B—C5B179.6 (2)
C7A—N1A—C6A—C1A−0.6 (2)C7B—N1B—C6B—C1B0.1 (2)
N2A—C1A—C6A—C5A−178.36 (18)N2B—C1B—C6B—C5B−179.5 (2)
C2A—C1A—C6A—C5A2.2 (3)C2B—C1B—C6B—C5B0.1 (3)
N2A—C1A—C6A—N1A0.2 (2)N2B—C1B—C6B—N1B0.0 (2)
C2A—C1A—C6A—N1A−179.23 (17)C2B—C1B—C6B—N1B179.6 (2)
C6A—N1A—C7A—N2A0.8 (2)C6B—N1B—C7B—N2B−0.2 (2)
C6A—N1A—C7A—S1A−179.74 (14)C6B—N1B—C7B—S1B179.98 (16)
C1A—N2A—C7A—N1A−0.8 (2)C1B—N2B—C7B—N1B0.2 (2)
C1A—N2A—C7A—S1A179.75 (12)C1B—N2B—C7B—S1B−179.95 (15)
C8A—S1A—C7A—N1A0.36 (18)C8B—S1B—C7B—N1B−0.7 (2)
C8A—S1A—C7A—N2A179.76 (14)C8B—S1B—C7B—N2B179.57 (16)
C7A—S1A—C8A—C9A178.84 (12)C7B—S1B—C8B—C9B179.89 (14)
C10A—N3A—C9A—C13A−1.6 (3)C10B—N3B—C9B—C13B0.3 (3)
C10A—N3A—C9A—C8A178.03 (17)C10B—N3B—C9B—C8B−179.8 (2)
S1A—C8A—C9A—N3A0.16 (19)S1B—C8B—C9B—N3B−0.3 (2)
S1A—C8A—C9A—C13A179.79 (13)S1B—C8B—C9B—C13B179.63 (16)
C9A—N3A—C10A—C11A1.0 (3)C9B—N3B—C10B—C11B−0.5 (4)
N3A—C10A—C11A—C12A0.4 (3)N3B—C10B—C11B—C12B0.1 (4)
C14A—O1A—C12A—C11A−0.3 (3)C14B—O1B—C12B—C11B6.8 (3)
C14A—O1A—C12A—C13A−179.93 (16)C14B—O1B—C12B—C13B−173.54 (19)
C10A—C11A—C12A—O1A179.03 (18)C10B—C11B—C12B—O1B−179.9 (2)
C10A—C11A—C12A—C13A−1.4 (3)C10B—C11B—C12B—C13B0.5 (3)
N3A—C9A—C13A—C12A0.7 (3)N3B—C9B—C13B—C12B0.2 (3)
C8A—C9A—C13A—C12A−178.93 (16)C8B—C9B—C13B—C12B−179.64 (18)
N3A—C9A—C13A—C16A179.90 (17)N3B—C9B—C13B—C16B−178.9 (2)
C8A—C9A—C13A—C16A0.3 (3)C8B—C9B—C13B—C16B1.2 (3)
O1A—C12A—C13A—C9A−179.52 (15)O1B—C12B—C13B—C9B179.70 (18)
C11A—C12A—C13A—C9A0.8 (3)C11B—C12B—C13B—C9B−0.7 (3)
O1A—C12A—C13A—C16A1.2 (2)O1B—C12B—C13B—C16B−1.1 (3)
C11A—C12A—C13A—C16A−178.39 (17)C11B—C12B—C13B—C16B178.5 (2)
C12A—O1A—C14A—C15A−176.73 (17)C12B—O1B—C14B—C15B171.8 (2)
O1A—C14A—C15A—F3A−60.9 (2)O1B—C14B—C15B—F2B−57.4 (3)
O1A—C14A—C15A—F2A60.1 (2)O1B—C14B—C15B—F3B62.7 (3)
O1A—C14A—C15A—F1A178.9 (2)O1B—C14B—C15B—F1B−177.4 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···OA0.861.952.771 (2)161
OA—HA1···N1Ai0.832.002.806 (2)161
N2B—H2BA···OB0.861.982.799 (3)160
OB—HB1···N1Bii0.842.032.798 (3)152
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···OA0.861.952.771 (2)161
OA—HA1···N1Ai0.832.002.806 (2)161
N2B—H2BA···OB0.861.982.799 (3)160
OB—HB1···N1Bii0.842.032.798 (3)152
Symmetry codes: (i) x+1, y, z; (ii) x, y−1, z.
Acknowledgements top

This work was supported by the "New Drug Innovation 2009ZX09301–007" project of the Ministry of Science and Technology of China.

references
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