#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/63/2206362.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_2206362
loop_
_publ_author_name
'K. Ravikumar'
'G. Y. S. K. Swamy'
'B. Sridhar'
'S. Roopa'
_publ_section_title
;
 Olazipinium nicotinate
;
_journal_coeditor_code           BT6703
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2720
_journal_page_last               o2723
_journal_paper_doi               10.1107/S160053680502369X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C17 H21 N4 S +, C6 H4 N O2 -'
_chemical_formula_moiety         'C17 H21 N4 S +, C6 H4 N O2 -'
_chemical_formula_sum            'C23 H25 N5 O2 S'
_chemical_formula_weight         435.54
_chemical_name_common            'Olanzapinium nicotinate'
_chemical_name_systematic
;
1-methyl-4-(2-methyl-10H-thieno[2,3-b][1,5]benzodiazepin-4-
yl)hexahydropyrazin-1-ium nicotinate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.164(2)
_cell_angle_beta                 87.485(2)
_cell_angle_gamma                83.735(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2565(10)
_cell_length_b                   11.2224(12)
_cell_length_c                   12.0629(13)
_cell_measurement_reflns_used    1483
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      21.20
_cell_measurement_theta_min      2.21
_cell_volume                     1111.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8110
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0569P)²+0.338P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1407
_reflns_number_gt                2885
_reflns_number_total             3894
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6703.cif
_cod_data_source_block           I
_cod_database_code               2206362
_cod_database_fobs_code          2206362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 0.59536(8) 0.24922(8) 0.40971(7) 0.0450(3) Uani d . 1 S
N1 0.2341(2) 0.4088(2) 0.1008(2) 0.0355(6) Uani d . 1 N
N2 0.3996(2) 0.3091(2) 0.0135(2) 0.0361(6) Uani d . 1 N
N3 0.4853(3) 0.2493(3) -0.1872(2) 0.0402(6) Uani d . 1 N
H3N 0.417(3) 0.182(3) -0.178(3) 0.058(9) Uiso d . 1 H
N4 0.2996(3) 0.2773(3) 0.3677(2) 0.0420(7) Uani d . 1 N
H4N 0.293(3) 0.244(3) 0.443(3) 0.029(8) Uiso d . 1 H
N5 -0.0937(4) -0.0773(4) 0.8549(4) 0.0990(13) Uani d . 1 N
C2 0.1899(3) 0.4651(3) 0.1817(3) 0.0348(7) Uani d . 1 C
C3 0.2153(3) 0.4037(3) 0.3109(3) 0.0370(7) Uani d . 1 C
C5 0.4409(3) 0.2794(3) 0.3209(2) 0.0326(7) Uani d . 1 C
C6 0.4739(3) 0.3157(3) 0.1998(2) 0.0309(6) Uani d . 1 C
C7 0.3603(3) 0.3456(3) 0.1067(2) 0.0309(6) Uani d . 1 C
C8 0.6275(3) 0.3206(3) 0.1787(3) 0.0361(7) Uani d . 1 C
H8 0.6686 0.3444 0.1007 0.043 Uiso calc R 1 H
C9 0.7071(3) 0.2877(3) 0.2811(3) 0.0389(7) Uani d . 1 C
C10 0.8684(3) 0.2870(4) 0.2919(3) 0.0556(9) Uani d . 1 C
H10A 0.9129 0.3068 0.2129 0.083 Uiso calc R 1 H
H10B 0.9080 0.2001 0.3526 0.083 Uiso calc R 1 H
H10C 0.8873 0.3536 0.3172 0.083 Uiso calc R 1 H
C11 0.1548(3) 0.4658(3) 0.3813(3) 0.0485(8) Uani d . 1 C
H11 0.1719 0.4250 0.4665 0.058 Uiso calc R 1 H
C12 0.0698(3) 0.5868(4) 0.3273(3) 0.0541(9) Uani d . 1 C
H12 0.0293 0.6264 0.3761 0.065 Uiso calc R 1 H
C13 0.0452(3) 0.6487(3) 0.2010(3) 0.0507(8) Uani d . 1 C
H13 -0.0099 0.7315 0.1637 0.061 Uiso calc R 1 H
C14 0.1027(3) 0.5873(3) 0.1300(3) 0.0419(7) Uani d . 1 C
H14 0.0828 0.6285 0.0452 0.050 Uiso calc R 1 H
C15 0.4882(3) 0.1845(3) 0.0371(3) 0.0384(7) Uani d . 1 C
H15A 0.4259 0.1137 0.0563 0.046 Uiso calc R 1 H
H15B 0.5513 0.1586 0.1080 0.046 Uiso calc R 1 H
C16 0.5780(3) 0.2023(3) -0.0746(3) 0.0424(8) Uani d . 1 C
H16A 0.6466 0.2672 -0.0887 0.051 Uiso calc R 1 H
H16B 0.6330 0.1177 -0.0593 0.051 Uiso calc R 1 H
C17 0.3870(3) 0.3715(3) -0.2055(3) 0.0430(8) Uani d . 1 C
H17A 0.3214 0.3953 -0.2745 0.052 Uiso calc R 1 H
H17B 0.4444 0.4460 -0.2259 0.052 Uiso calc R 1 H
C18 0.3002(3) 0.3476(3) -0.0901(2) 0.0392(7) Uani d . 1 C
H18A 0.2390 0.4286 -0.1027 0.047 Uiso calc R 1 H
H18B 0.2382 0.2768 -0.0721 0.047 Uiso calc R 1 H
C19 0.5742(4) 0.2733(4) -0.2993(3) 0.0647(10) Uani d . 1 C
H19A 0.5113 0.3011 -0.3697 0.097 Uiso calc R 1 H
H19B 0.6328 0.1921 -0.2865 0.097 Uiso calc R 1 H
H19C 0.6360 0.3424 -0.3143 0.097 Uiso calc R 1 H
O1 0.2962(2) 0.0798(2) 0.83969(18) 0.0513(6) Uani d . 1 O
O2 0.2842(3) 0.1911(3) 0.6352(2) 0.0734(8) Uani d . 1 O
C20 0.0985(3) 0.0536(3) 0.7389(3) 0.0384(7) Uani d . 1 C
C21 0.0265(4) 0.0805(4) 0.6313(3) 0.0564(9) Uani d . 1 C
H21 0.0660 0.1344 0.5549 0.068 Uiso calc R 1 H
C22 -0.1005(4) 0.0299(4) 0.6347(4) 0.0634(10) Uani d . 1 C
H22 -0.1482 0.0484 0.5617 0.076 Uiso calc R 1 H
C23 -0.1560(4) -0.0472(5) 0.7451(5) 0.0826(13) Uani d . 1 C
H23 -0.2429 -0.0823 0.7464 0.099 Uiso calc R 1 H
C24 0.0345(4) -0.0269(4) 0.8485(3) 0.0658(10) Uani d . 1 C
H24 0.0818 -0.0481 0.9224 0.079 Uiso calc R 1 H
C25 0.2379(3) 0.1118(3) 0.7362(3) 0.0389(7) Uani d . 1 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C5 S1 C9 91.83(13) ?
C7 N1 C2 123.1(2) y
C7 N2 C15 122.5(2) ?
C7 N2 C18 119.4(2) ?
C15 N2 C18 110.6(2) y
C19 N3 C16 111.5(2) y
C19 N3 C17 111.2(2) y
C16 N3 C17 110.9(2) y
C19 N3 H3N 107.5(17) ?
C16 N3 H3N 111.4(17) ?
C17 N3 H3N 104.1(17) ?
C5 N4 C3 113.3(2) y
C5 N4 H4N 115.6(19) ?
C3 N4 H4N 111.3(19) ?
C23 N5 C24 115.9(3) y
C14 C2 N1 116.4(2) ?
C14 C2 C3 117.7(3) ?
N1 C2 C3 125.7(3) ?
C11 C3 C2 119.6(3) ?
C11 C3 N4 120.9(3) ?
C2 C3 N4 119.4(3) ?
C6 C5 N4 124.7(2) ?
C6 C5 S1 111.7(2) ?
N4 C5 S1 123.4(2) ?
C5 C6 C8 111.6(2) ?
C5 C6 C7 121.5(2) ?
C8 C6 C7 126.9(2) ?
N1 C7 N2 118.4(2) y
N1 C7 C6 126.0(2) y
N2 C7 C6 115.4(2) y
C9 C8 C6 114.5(3) ?
C9 C8 H8 122.7 ?
C6 C8 H8 122.7 ?
C8 C9 C10 128.6(3) ?
C8 C9 S1 110.4(2) ?
C10 C9 S1 120.9(2) ?
C9 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C9 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C12 C11 C3 121.3(3) ?
C12 C11 H11 119.4 ?
C3 C11 H11 119.4 ?
C13 C12 C11 119.8(3) ?
C13 C12 H12 120.1 ?
C11 C12 H12 120.1 ?
C12 C13 C14 119.6(3) ?
C12 C13 H13 120.2 ?
C14 C13 H13 120.2 ?
C13 C14 C2 122.0(3) ?
C13 C14 H14 119.0 ?
C2 C14 H14 119.0 ?
N2 C15 C16 110.1(2) ?
N2 C15 H15A 109.6 ?
C16 C15 H15A 109.6 ?
N2 C15 H15B 109.6 ?
C16 C15 H15B 109.6 ?
H15A C15 H15B 108.2 ?
N3 C16 C15 111.3(2) ?
N3 C16 H16A 109.4 ?
C15 C16 H16A 109.4 ?
N3 C16 H16B 109.4 ?
C15 C16 H16B 109.4 ?
H16A C16 H16B 108.0 ?
N3 C17 C18 110.9(2) ?
N3 C17 H17A 109.5 ?
C18 C17 H17A 109.5 ?
N3 C17 H17B 109.5 ?
C18 C17 H17B 109.5 ?
H17A C17 H17B 108.1 ?
N2 C18 C17 109.1(2) ?
N2 C18 H18A 109.9 ?
C17 C18 H18A 109.9 ?
N2 C18 H18B 109.9 ?
C17 C18 H18B 109.9 ?
H18A C18 H18B 108.3 ?
N3 C19 H19A 109.5 ?
N3 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
N3 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C24 C20 C21 116.4(3) ?
C24 C20 C25 121.9(3) ?
C21 C20 C25 121.7(3) ?
C22 C21 C20 121.2(3) ?
C22 C21 H21 119.4 ?
C20 C21 H21 119.4 ?
C23 C22 C21 118.7(4) ?
C23 C22 H22 120.6 ?
C21 C22 H22 120.6 ?
C22 C23 N5 124.0(4) ?
C22 C23 H23 118.0 ?
N5 C23 H23 118.0 ?
N5 C24 C20 123.7(3) ?
N5 C24 H24 118.2 ?
C20 C24 H24 118.2 ?
O2 C25 O1 124.5(3) y
O2 C25 C20 118.7(3) y
O1 C25 C20 116.8(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 1.734(3) y
S1 C9 1.736(3) y
N1 C7 1.285(3) y
N1 C2 1.409(3) y
N2 C7 1.382(3) ?
N2 C15 1.456(3) ?
N2 C18 1.456(3) ?
N3 C19 1.483(4) y
N3 C16 1.489(4) y
N3 C17 1.493(4) y
N3 H3N 1.00(3) ?
N4 C5 1.400(3) y
N4 C3 1.421(4) y
N4 H4N 0.81(3) ?
N5 C23 1.349(5) y
N5 C24 1.354(5) y
C2 C14 1.396(4) ?
C2 C3 1.409(4) ?
C3 C11 1.389(4) ?
C5 C6 1.358(4) ?
C6 C8 1.435(4) ?
C6 C7 1.473(4) ?
C8 C9 1.347(4) ?
C8 H8 0.9300 ?
C9 C10 1.504(4) ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 C12 1.378(4) ?
C11 H11 0.9300 ?
C12 C13 1.377(4) ?
C12 H12 0.9300 ?
C13 C14 1.380(4) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 C16 1.496(4) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 C18 1.506(4) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
O1 C25 1.261(3) y
O2 C25 1.233(3) y
C20 C24 1.373(4) ?
C20 C21 1.378(4) ?
C20 C25 1.501(4) ?
C21 C22 1.351(5) ?
C21 H21 0.9300 ?
C22 C23 1.336(5) ?
C22 H22 0.9300 ?
C23 H23 0.9300 ?
C24 H24 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3N O1 1_554 1.00(3) 1.63(3) 2.628(3) 175(3)
N3 H3N O2 1_554 1.00(3) 2.57(3) 3.219(3) 122(2)
N4 H4N O2 . 0.81(3) 2.12(3) 2.922(3) 170(3)
C19 H19A O2 1_554 0.96 2.54 3.173(4) 124
C17 H17B Cg1 2_665 0.97 2.72 3.55 144
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 N1 C2 C14 143.1(3)
C7 N1 C2 C3 -42.8(4)
C14 C2 C3 C11 -0.5(4)
N1 C2 C3 C11 -174.5(3)
C14 C2 C3 N4 178.0(2)
N1 C2 C3 N4 4.0(4)
C5 N4 C3 C11 -121.8(3)
C5 N4 C3 C2 59.7(3)
C3 N4 C5 C6 -58.2(4)
C3 N4 C5 S1 116.2(3)
C9 S1 C5 C6 0.5(2)
C9 S1 C5 N4 -174.4(2)
N4 C5 C6 C8 174.2(2)
S1 C5 C6 C8 -0.7(3)
N4 C5 C6 C7 -5.5(4)
S1 C5 C6 C7 179.6(2)
C2 N1 C7 N2 -171.9(2)
C2 N1 C7 C6 3.4(4)
C15 N2 C7 N1 -144.5(3)
C18 N2 C7 N1 2.3(4)
C15 N2 C7 C6 39.8(4)
C18 N2 C7 C6 -173.4(2)
C5 C6 C7 N1 39.0(4)
C8 C6 C7 N1 -140.7(3)
C5 C6 C7 N2 -145.6(3)
C8 C6 C7 N2 34.7(4)
C5 C6 C8 C9 0.6(4)
C7 C6 C8 C9 -179.7(3)
C6 C8 C9 C10 -177.6(3)
C6 C8 C9 S1 -0.1(3)
C5 S1 C9 C8 -0.2(2)
C5 S1 C9 C10 177.4(3)
C2 C3 C11 C12 0.1(4)
N4 C3 C11 C12 -178.3(3)
C3 C11 C12 C13 -0.7(5)
C11 C12 C13 C14 1.7(5)
C12 C13 C14 C2 -2.1(5)
N1 C2 C14 C13 176.0(3)
C3 C2 C14 C13 1.5(4)
C7 N2 C15 C16 -149.3(2)
C18 N2 C15 C16 61.3(3)
C19 N3 C16 C15 177.3(3)
C17 N3 C16 C15 52.8(3)
N2 C15 C16 N3 -56.3(3)
C19 N3 C17 C18 -178.4(2)
C16 N3 C17 C18 -53.7(3)
C7 N2 C18 C17 147.6(2)
C15 N2 C18 C17 -61.9(3)
N3 C17 C18 N2 57.9(3)
C24 C20 C21 C22 0.2(5)
C25 C20 C21 C22 -178.6(3)
C20 C21 C22 C23 0.1(6)
C21 C22 C23 N5 0.7(7)
C24 N5 C23 C22 -1.7(7)
C23 N5 C24 C20 2.0(6)
C21 C20 C24 N5 -1.3(5)
C25 C20 C24 N5 177.5(3)
C24 C20 C25 O2 -174.8(3)
C21 C20 C25 O2 4.0(5)
C24 C20 C25 O1 2.1(4)
C21 C20 C25 O1 -179.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129163
