#------------------------------------------------------------------------------
#$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011623.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2011623
loop_
_publ_author_name
'Vyas, K.'
'Sivalakshmidevi, A.'
'Om Reddy, G.'
_publ_section_title
;
 Lansoprazole, an antiulcerative drug
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e572
_journal_page_last               e573
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C16 H14 F3 N3 O2 S'
_chemical_formula_sum            'C16 H14 F3 N3 O2 S'
_chemical_formula_weight         369.36
_chemical_name_common            lansoprazole
_chemical_name_systematic
;
2-({[3-methyl-4-(2,2,2-trifluroethoxy)-2-pyridinyl]methyl}-
sulfinyl)-1H-benzimidazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 102.032(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   15.8700(10)
_cell_length_b                   7.3481(8)
_cell_length_c                   14.2620(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.2
_cell_measurement_theta_max      48.2
_cell_measurement_theta_min      32.5
_cell_volume                     1626.6(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1993)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SIR92 (Altomare et. al. 1993)'
_diffrn_ambient_temperature      298.2
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  .021
_diffrn_reflns_av_sigmaI/netI    .040
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3347
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         70.08
_diffrn_reflns_theta_min         2.85
_diffrn_standards_decay_%        .06
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.223
_exptl_absorpt_correction_T_max  .513
_exptl_absorpt_correction_T_min  .365
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760.00
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .30
_refine_diff_density_max         .25
_refine_diff_density_min         -.38
_refine_ls_extinction_coef       6E-6(1)
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.916
_refine_ls_goodness_of_fit_ref   1.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2853
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .049
_refine_ls_R_factor_gt           .047
_refine_ls_shift/su_max          .0004
_refine_ls_shift/su_mean         .0004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00016|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .078
_refine_ls_wR_factor_ref         .077
_reflns_number_gt                2853
_reflns_number_total             2961
_reflns_threshold_expression     I>0.1\s(I)
_[local]_cod_data_source_file    qa0397.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1626.7(2)
_cod_database_code               2011623
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'  -x,1/2+y,1/2-z'
'  -x,  -y,  -z'
'  +x,1/2-y,1/2+z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
S1 -.01220(3) -.11105(6) .38378(4) .0457(2) Uani d ? . 1.000
F1 -.48890(10) -.3803(3) .1126(2) .1220(9) Uani d ? . 1.000
F2 -.51580(10) -.5022(4) .2375(2) .1130(8) Uani d ? . 1.000
F3 -.52930(10) -.6580(3) .1113(2) .1161(8) Uani d ? . 1.000
O1 -.34187(9) -.4545(2) .24220(10) .0549(4) Uani d ? . 1.000
O2 -.04880(10) -.1399(2) .27970(10) .0598(5) Uani d ? . 1.000
N1 .15470(10) -.1606(2) .46620(10) .0436(4) Uani d ? . 1.000
N2 .09910(10) -.4009(2) .37810(10) .0427(4) Uani d ? . 1.000
N3 -.08760(10) -.5425(2) .37560(10) .0424(4) Uani d ? . 1.000
C1 .18400(10) -.4419(3) .41370(10) .0422(5) Uani d ? . 1.000
C2 .2341(2) -.5932(3) .4013(2) .0590(7) Uani d ? . 1.000
C3 .3193(2) -.5869(4) .4475(2) .0682(8) Uani d ? . 1.000
C4 .35390(10) -.4390(4) .5037(2) .0659(7) Uani d ? . 1.000
C5 .30460(10) -.2915(4) .5157(2) .0557(6) Uani d ? . 1.000
C6 .21790(10) -.2926(3) .46840(10) .0423(5) Uani d ? . 1.000
C7 .08690(10) -.2343(3) .41210(10) .0402(5) Uani d ? . 1.000
C8 -.07670(10) -.2506(3) .45030(10) .0428(5) Uani d ? . 1.000
C9 -.12940(10) -.3870(2) .38560(10) .0366(5) Uani d ? . 1.000
C10 -.21410(10) -.3500(3) .33960(10) .0390(5) Uani d ? . 1.000
C11 -.25760(10) -.4901(3) .28350(10) .0403(5) Uani d ? . 1.000
C12 -.21650(10) -.6515(3) .2725(2) .0451(5) Uani d ? . 1.000
C13 -.13130(10) -.6696(3) .31980(10) .0453(5) Uani d ? . 1.000
C14 -.3902(2) -.5970(3) .1906(2) .0628(7) Uani d ? . 1.000
C15 -.4804(2) -.5328(5) .1633(2) .0740(9) Uani d ? . 1.000
C16 -.25830(10) -.1721(3) .3493(2) .0522(6) Uani d ? . 1.000
H1 .056(2) -.446(4) .349(2) .060(8) Uiso d ? . 1.000
H2 .2071 -.6947 .3648 .082 Uiso c ? . 1.000
H3 .3546 -.6765 .4429 .077 Uiso c ? . 1.000
H4 .4149 -.4425 .5381 .080 Uiso c ? . 1.000
H5 .3310 -.1886 .5560 .070 Uiso c ? . 1.000
H6 -.0385 -.3118 .5012 .040 Uiso c ? . 1.000
H7 -.1133 -.1686 .4720 .045 Uiso c ? . 1.000
H8 -.2448 -.7512 .2293 .056 Uiso c ? . 1.000
H9 -.0986 -.7799 .3126 .047 Uiso c ? . 1.000
H10 -.3696 -.6281 .1327 .090 Uiso c ? . 1.000
H11 -.3911 -.6980 .2225 .070 Uiso c ? . 1.000
H12 -.3072 -.1531 .3005 .084 Uiso c ? . 1.000
H13 -.2275 -.0736 .3340 .127 Uiso c ? . 1.000
H14 -.2687 -.1564 .4113 .127 Uiso c ? . 1.000
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 .0355(3) .0317(3) .0636(4) .0007(2) -.0040(2) .0060(2)
F1 .0670(10) .124(2) .152(2) -.0050(10) -.0310(10) .044(2)
F2 .0610(10) .147(2) .138(2) -.0030(10) .0360(10) -.029(2)
F3 .0566(9) .132(2) .144(2) -.0300(10) -.0160(10) -.0430(10)
O1 .0352(8) .0482(9) .0730(10) -.0013(6) -.0066(7) -.0101(7)
O2 .0475(8) .0660(10) .0575(9) -.0044(7) -.0080(7) .0238(8)
N1 .0343(8) .0416(9) .0520(9) -.0026(7) .0021(7) -.0031(7)
N2 .0390(9) .0369(9) .0475(9) -.0019(6) -.0019(7) -.0018(7)
N3 .0364(8) .0385(9) .0509(9) .0053(6) .0060(7) -.0012(7)
C1 .0410(10) .0440(10) .0410(10) .0038(8) .0064(8) .0026(8)
C2 .0590(10) .0520(10) .0650(10) .0140(10) .0130(10) -.0050(10)
C3 .0560(10) .072(2) .079(2) .0270(10) .0180(10) .0080(10)
C4 .0380(10) .084(2) .073(2) .0110(10) .0070(10) .0080(10)
C5 .0340(10) .0700(10) .0600(10) -.0030(10) .0029(9) -.0010(10)
C6 .0345(9) .0460(10) .0450(10) .0009(8) .0060(8) .0022(8)
C7 .0347(9) .0361(9) .0460(10) -.0016(7) .0005(7) .0017(8)
C8 .0346(9) .0410(10) .0490(10) .0032(7) .0003(8) -.0050(8)
C9 .0302(9) .0341(9) .0441(9) .0026(7) .0047(7) .0016(7)
C10 .0310(9) .0344(9) .0500(10) .0014(7) .0048(8) -.0014(8)
C11 .0320(9) .0410(10) .0460(10) -.0006(7) .0051(7) -.0001(8)
C12 .0430(10) .0357(9) .0550(10) -.0022(8) .0059(8) -.0075(8)
C13 .0430(10) .0360(10) .0560(10) .0080(8) .0083(9) -.0029(8)
C14 .0450(10) .0600(10) .079(2) -.0100(10) .0010(10) -.0160(10)
C15 .0430(10) .082(2) .089(2) -.0120(10) -.0040(10) -.008(2)
C16 .0400(10) .0390(10) .0720(10) .0098(8) .0015(9) -.0070(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . . 1.493(2) yes
S1 C7 . . 1.787(2) yes
S1 C8 . . 1.845(2) yes
F1 C15 . . 1.325(4) yes
F2 C15 . . 1.317(4) yes
F3 C15 . . 1.326(3) yes
O1 C11 . . 1.369(2) yes
O1 C14 . . 1.411(3) yes
N1 C6 . . 1.391(3) yes
N1 C7 . . 1.304(2) yes
N2 C1 . . 1.371(2) yes
N2 C7 . . 1.345(3) yes
N2 H1 . . .79(3) no
N3 C9 . . 1.344(2) yes
N3 C13 . . 1.325(3) yes
C1 C2 . . 1.400(3) yes
C1 C6 . . 1.389(3) yes
C2 C3 . . 1.376(4) yes
C2 H2 . . .96 no
C3 C4 . . 1.394(4) yes
C3 H3 . . .88 no
C4 C5 . . 1.367(4) yes
C4 H4 . . .99 no
C5 C6 . . 1.401(3) yes
C5 H5 . . .99 no
C8 C9 . . 1.495(2) yes
C8 H6 . . .96 no
C8 H7 . . .93 no
C9 C10 . . 1.394(2) yes
C10 C11 . . 1.395(3) yes
C10 C16 . . 1.503(3) yes
C11 C12 . . 1.378(3) yes
C12 C13 . . 1.385(3) yes
C12 H8 . . 1.00 no
C13 H9 . . .98 no
C14 C15 . . 1.481(4) yes
C14 H10 . . .98 no
C14 H11 . . .87 no
C16 H12 . . .94 no
C16 H13 . . .93 no
C16 H14 . . .94 no
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .017 .009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H .000 .000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
F .069 .053
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N .029 .018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O .047 .032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
S .319 .557
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 1
-3 -1 1
-2 0 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 S1 C7 107.10(9) yes
O2 S1 C8 106.88(9) yes
C7 S1 C8 99.11(9) yes
C11 O1 C14 117.3(2) yes
C6 N1 C7 103.0(2) yes
C1 N2 C7 105.7(2) yes
C1 N2 H1 141(2) no
C7 N2 H1 113(2) no
C9 N3 C13 117.1(2) yes
N2 C1 C2 132.0(2) yes
N2 C1 C6 105.7(2) yes
C2 C1 C6 122.3(2) yes
C1 C2 C3 116.1(2) yes
C1 C2 H2 119.1 no
C3 C2 H2 124.7 no
C2 C3 C4 122.1(2) yes
C2 C3 H3 121.3 no
C4 C3 H3 116.6 no
C3 C4 C5 121.6(2) yes
C3 C4 H4 119.4 no
C5 C4 H4 119.0 no
C4 C5 C6 117.7(2) yes
C4 C5 H5 119.7 no
C6 C5 H5 122.5 no
N1 C6 C1 110.2(2) yes
N1 C6 C5 129.7(2) yes
C1 C6 C5 120.1(2) yes
S1 C7 N1 120.10(10) yes
S1 C7 N2 124.50(10) yes
N1 C7 N2 115.4(2) yes
S1 C8 C9 110.80(10) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
F1 F3 3.278(3) 3_445 no
F1 F2 3.497(4) 2_455 no
F1 C5 3.515(3) 4_444 no
F1 C4 3.540(4) 4_444 no
F2 F3 3.304(4) 2_455 no
F2 C14 3.575(3) 2_455 no
F3 C3 3.522(3) 4_434 no
F3 C16 3.532(3) 2_445 no
O2 N2 2.835(2) 2 no
O2 C1 3.443(2) 2 no
O2 C13 3.453(3) 2 no
O2 N3 3.478(2) 2 no
O2 C2 3.502(3) 2 no
N1 C13 3.388(3) 3_546 no
N1 N3 3.462(2) 3_546 no
N1 C8 3.563(3) 3_556 no
N2 C13 3.423(3) 2 no
N2 N3 3.580(2) 3_546 no
N3 C7 3.442(2) 3_546 no
N3 C8 3.546(2) 3_546 no
N3 C6 3.551(2) 3_546 no
C1 C9 3.399(3) 3_546 no
C1 C12 3.528(3) 2 no
C5 C11 3.496(3) 3_546 no
C6 C13 3.580(3) 3_546 no
C6 C12 3.585(3) 2 no
C7 C13 3.554(3) 2 no