#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/49/2204932.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_2204932
loop_
_publ_author_name
'Yathirajan, Hemmige S.'
'Nagaraj, Basavegowda'
'Nagaraja, Padmarajaiah'
'Bolte, Michael'
_publ_section_title
;
 Pioglitazone hydrochloride
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o154
_journal_page_last               o155
_journal_paper_doi               10.1107/S1600536804033100
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C19 H21 N2 O3 S +, Cl -'
_chemical_formula_moiety         'C19 H21 N2 O3 S +, Cl -'
_chemical_formula_sum            'C19 H21 Cl N2 O3 S'
_chemical_formula_weight         392.89
_chemical_name_common            'Pioglitazone hydrochloride'
_chemical_name_systematic
;(+-)-5-({4-[2-(5-ethyl-2-pyridinio)ethoxy]phenyl}methyl)thiazolidine-2,4-dione
chloride
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.178(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0696(17)
_cell_length_b                   9.4318(16)
_cell_length_c                   10.1752(19)
_cell_measurement_reflns_used    5341
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      3.8
_cell_volume                     962.4(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  'SHELXL97 and PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Stoe IPDS-II two-circle'
_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  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4956
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.65
_diffrn_reflns_theta_min         4.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.9648
_exptl_absorpt_correction_T_min  0.8718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 1990; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.199
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3274
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0348
_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)+(0.0375P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                2480
_reflns_number_total             3274
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc6013.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2204932
_cod_database_fobs_code          2204932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.84700(8) 1.04424(7) 0.30091(7) 0.0413(2) Uani d . 1 . . Cl
O1 0.7412(2) 0.8025(2) 0.7798(2) 0.0442(6) Uani d . 1 . . O
C2 0.7244(3) 0.7220(3) 0.6599(3) 0.0393(8) Uani d . 1 . . C
H2A 0.6458 0.7559 0.6031 0.047 Uiso calc R 1 . . H
H2B 0.7123 0.6202 0.6791 0.047 Uiso calc R 1 . . H
C3 0.8506(3) 0.7450(3) 0.5930(3) 0.0387(7) Uani d . 1 . . C
H3A 0.8581 0.8466 0.5704 0.046 Uiso calc R 1 . . H
H3B 0.9285 0.7200 0.6551 0.046 Uiso calc R 1 . . H
C11 0.6450(4) 0.7889(3) 0.8672(3) 0.0408(8) Uani d . 1 A . C
C12 0.5246(4) 0.7200(3) 0.8399(3) 0.0459(8) Uani d . 1 . . C
H12 0.5034 0.6747 0.7572 0.055 Uiso calc R 1 . . H
C13 0.4353(4) 0.7186(4) 0.9363(4) 0.0579(11) Uani d . 1 A . C
H13 0.3520 0.6719 0.9184 0.069 Uiso calc R 1 . . H
C14 0.4644(5) 0.7840(4) 1.0588(4) 0.0601(12) Uani d D 1 . . C
C15 0.5853(5) 0.8491(4) 1.0827(4) 0.0568(11) Uani d . 1 A . C
H15 0.6080 0.8924 1.1660 0.068 Uiso calc R 1 . . H
C16 0.6745(4) 0.8530(3) 0.9888(3) 0.0476(9) Uani d . 1 . . C
H16 0.7575 0.9001 1.0072 0.057 Uiso calc R 1 A . H
C17 0.3732(7) 0.7983(6) 1.1705(6) 0.0372(16) Uani d PD 0.660(11) A 1 C
H17A 0.2843 0.8328 1.1349 0.045 Uiso calc PR 0.660(11) A 1 H
H17B 0.4113 0.8676 1.2366 0.045 Uiso calc PR 0.660(11) A 1 H
C17' 0.3414(11) 0.7263(18) 1.1331(10) 0.046(3) Uani d PD 0.340(11) A 2 C
H17C 0.2635 0.7902 1.1180 0.055 Uiso calc PR 0.340(11) A 2 H
H17D 0.3151 0.6300 1.1019 0.055 Uiso calc PR 0.340(11) A 2 H
C21 0.3599(5) 0.6538(6) 1.2352(5) 0.0328(14) Uani d PD 0.660(11) A 1 C
H21 0.3185 0.5843 1.1695 0.039 Uiso calc PR 0.660(11) A 1 H
C21' 0.3918(9) 0.7241(13) 1.2754(9) 0.036(3) Uani d PD 0.340(11) A 2 C
H21' 0.4243 0.8193 1.3073 0.043 Uiso calc PR 0.340(11) A 2 H
S22 0.51855(8) 0.58585(9) 1.31002(8) 0.0452(2) Uani d D 1 . . S
C23 0.4497(3) 0.5414(4) 1.4576(3) 0.0406(7) Uani d . 1 A . C
O23 0.5067(3) 0.4735(3) 1.5462(3) 0.0670(8) Uani d . 1 . . O
N24 0.3248(2) 0.5972(3) 1.4607(2) 0.0404(6) Uani d . 1 . . N
H24 0.274(4) 0.586(4) 1.531(3) 0.064(10) Uiso d . 1 . . H
C25 0.2730(4) 0.6694(4) 1.3520(3) 0.0505(9) Uani d D 1 A . C
O25 0.1645(3) 0.7265(3) 1.3422(3) 0.0633(7) Uani d . 1 . . O
C31 0.8535(3) 0.6576(3) 0.4696(3) 0.0354(7) Uani d . 1 . . C
N32 0.8643(3) 0.7268(3) 0.3565(3) 0.0376(7) Uani d . 1 . . N
H32 0.868(3) 0.808(3) 0.359(3) 0.026(9) Uiso d . 1 . . H
C33 0.8737(4) 0.6605(4) 0.2409(3) 0.0426(8) Uani d . 1 . . C
H33 0.8827 0.7153 0.1639 0.051 Uiso calc R 1 . . H
C34 0.8708(4) 0.5160(3) 0.2315(3) 0.0452(9) Uani d . 1 . . C
C35 0.8561(4) 0.4409(3) 0.3478(3) 0.0404(8) Uani d . 1 . . C
H35 0.8501 0.3404 0.3455 0.048 Uiso calc R 1 . . H
C36 0.8504(3) 0.5116(3) 0.4660(3) 0.0396(8) Uani d . 1 . . C
H36 0.8442 0.4595 0.5450 0.047 Uiso calc R 1 . . H
C37 0.8849(6) 0.4391(5) 0.1034(4) 0.0779(14) Uani d . 1 . . C
H37A 0.9448 0.3570 0.1227 0.093 Uiso calc R 1 . . H
H37B 0.7963 0.4009 0.0712 0.093 Uiso calc R 1 . . H
C38 0.9358(5) 0.5198(5) -0.0044(4) 0.0860(15) Uani d . 1 . . C
H38A 0.9418 0.4576 -0.0808 0.129 Uiso calc R 1 . . H
H38B 1.0245 0.5571 0.0245 0.129 Uiso calc R 1 . . H
H38C 0.8752 0.5987 -0.0289 0.129 Uiso calc R 1 . . H
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'
Cl Cl 0.1484 0.1585 '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
C11 O1 C2 117.6(2) ?
O1 C2 C3 105.5(3) ?
O1 C2 H2A 110.6 ?
C3 C2 H2A 110.6 ?
O1 C2 H2B 110.6 ?
C3 C2 H2B 110.6 ?
H2A C2 H2B 108.8 ?
C31 C3 C2 112.2(3) ?
C31 C3 H3A 109.2 ?
C2 C3 H3A 109.2 ?
C31 C3 H3B 109.2 ?
C2 C3 H3B 109.2 ?
H3A C3 H3B 107.9 ?
O1 C11 C12 124.7(3) ?
O1 C11 C16 115.4(3) ?
C12 C11 C16 119.9(3) ?
C11 C12 C13 118.3(3) ?
C11 C12 H12 120.8 ?
C13 C12 H12 120.8 ?
C12 C13 C14 121.9(4) ?
C12 C13 H13 119.1 ?
C14 C13 H13 119.1 ?
C15 C14 C13 118.0(4) ?
C15 C14 C17 114.4(4) ?
C13 C14 C17 127.5(5) ?
C15 C14 C17' 141.5(6) ?
C13 C14 C17' 99.3(6) ?
C14 C15 C16 121.2(4) ?
C14 C15 H15 119.4 ?
C16 C15 H15 119.4 ?
C15 C16 C11 120.7(4) ?
C15 C16 H16 119.7 ?
C11 C16 H16 119.7 ?
C14 C17 C21 108.9(4) ?
C14 C17 H17A 109.9 ?
C21 C17 H17A 109.9 ?
C14 C17 H17B 109.9 ?
C21 C17 H17B 109.9 ?
H17A C17 H17B 108.3 ?
C21' C17' C14 104.6(8) ?
C21' C17' H17C 110.8 ?
C14 C17' H17C 110.8 ?
C21' C17' H17D 110.8 ?
C14 C17' H17D 110.8 ?
H17C C17' H17D 108.9 ?
C25 C21 C17 109.0(4) ?
C25 C21 S22 104.3(3) y
C17 C21 S22 112.8(5) ?
C25 C21 H21 110.2 ?
C17 C21 H21 110.2 ?
S22 C21 H21 110.2 ?
C17' C21' C25 106.1(8) ?
C17' C21' S22 111.5(9) ?
C25 C21' S22 102.6(5) ?
C17' C21' H21' 112.0 ?
C25 C21' H21' 112.0 ?
S22 C21' H21' 112.0 ?
C23 S22 C21 92.44(18) y
C23 S22 C21' 90.7(3) ?
O23 C23 N24 124.3(3) ?
O23 C23 S22 124.5(3) ?
N24 C23 S22 111.2(2) y
C25 N24 C23 117.4(3) y
C25 N24 H24 119(2) ?
C23 N24 H24 123(2) ?
O25 C25 N24 124.4(3) ?
O25 C25 C21 123.1(3) ?
N24 C25 C21 112.0(3) y
O25 C25 C21' 122.2(4) ?
N24 C25 C21' 108.3(4) ?
N32 C31 C36 117.9(3) ?
N32 C31 C3 117.4(3) ?
C36 C31 C3 124.6(3) ?
C31 N32 C33 123.0(3) ?
C31 N32 H32 118(2) ?
C33 N32 H32 119(2) ?
N32 C33 C34 121.5(3) ?
N32 C33 H33 119.2 ?
C34 C33 H33 119.2 ?
C33 C34 C35 116.7(3) ?
C33 C34 C37 122.5(3) ?
C35 C34 C37 120.9(3) ?
C36 C35 C34 120.6(3) ?
C36 C35 H35 119.7 ?
C34 C35 H35 119.7 ?
C31 C36 C35 120.2(3) ?
C31 C36 H36 119.9 ?
C35 C36 H36 119.9 ?
C38 C37 C34 117.6(3) ?
C38 C37 H37A 107.9 ?
C34 C37 H37A 107.9 ?
C38 C37 H37B 107.9 ?
C34 C37 H37B 107.9 ?
H37A C37 H37B 107.2 ?
C37 C38 H38A 109.5 ?
C37 C38 H38B 109.5 ?
H38A C38 H38B 109.5 ?
C37 C38 H38C 109.5 ?
H38A C38 H38C 109.5 ?
H38B C38 H38C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.379(4) ?
O1 C2 1.434(4) ?
C2 C3 1.510(4) ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C31 1.505(4) ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C11 C12 1.381(5) ?
C11 C16 1.385(5) ?
C12 C13 1.390(5) ?
C12 H12 0.9500 ?
C13 C14 1.398(6) ?
C13 H13 0.9500 ?
C14 C15 1.366(6) ?
C14 C17 1.531(6) ?
C14 C17' 1.604(10) ?
C15 C16 1.370(5) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
C17 C21 1.524(7) ?
C17 H17A 0.9900 ?
C17 H17B 0.9900 ?
C17' C21' 1.491(13) ?
C17' H17C 0.9900 ?
C17' H17D 0.9900 ?
C21 C25 1.546(5) y
C21 S22 1.823(5) y
C21 H21 1.0000 ?
C21' C25 1.573(9) ?
C21' S22 1.836(9) ?
C21' H21' 1.0000 ?
S22 C23 1.760(3) y
C23 O23 1.208(4) ?
C23 N24 1.366(4) y
N24 C25 1.362(4) y
N24 H24 0.93(4) ?
C25 O25 1.214(4) ?
C31 N32 1.336(4) ?
C31 C36 1.378(4) ?
N32 C33 1.343(4) ?
N32 H32 0.76(3) ?
C33 C34 1.366(4) ?
C33 H33 0.9500 ?
C34 C35 1.399(5) ?
C34 C37 1.509(5) ?
C35 C36 1.380(4) ?
C35 H35 0.9500 ?
C36 H36 0.9500 ?
C37 C38 1.465(6) ?
C37 H37A 0.9900 ?
C37 H37B 0.9900 ?
C38 H38A 0.9800 ?
C38 H38B 0.9800 ?
C38 H38C 0.9800 ?
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
N32 H32 Cl1 . 0.76(3) 2.31(3) 3.049(3) 162(3)
N24 H24 Cl1 2_647 0.93(4) 2.22(4) 3.144(3) 176(3)
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
C11 O1 C2 C3 -173.7(3)
O1 C2 C3 C31 175.5(3)
C2 O1 C11 C12 -9.8(4)
C2 O1 C11 C16 171.5(3)
O1 C11 C12 C13 -177.9(3)
C16 C11 C12 C13 0.7(5)
C11 C12 C13 C14 -0.3(5)
C12 C13 C14 C15 -0.7(5)
C12 C13 C14 C17 176.2(4)
C12 C13 C14 C17' -170.9(6)
C13 C14 C15 C16 1.3(5)
C17 C14 C15 C16 -176.0(4)
C17' C14 C15 C16 165.7(10)
C14 C15 C16 C11 -1.0(5)
O1 C11 C16 C15 178.6(3)
C12 C11 C16 C15 -0.1(5)
C15 C14 C17 C21 -110.6(6)
C13 C14 C17 C21 72.4(7)
C17' C14 C17 C21 46.7(9)
C15 C14 C17' C21' -13.8(18)
C13 C14 C17' C21' 152.2(10)
C17 C14 C17' C21' -48.2(8)
C14 C17 C21 C25 177.5(4)
C14 C17 C21 S22 62.1(6)
C14 C17' C21' C25 179.4(7)
C14 C17' C21' S22 -69.5(13)
C25 C21 S22 C23 14.3(4)
C17 C21 S22 C23 132.4(4)
C25 C21 S22 C21' -72.4(7)
C17 C21 S22 C21' 45.8(7)
C17' C21' S22 C23 -139.0(9)
C25 C21' S22 C23 -25.7(6)
C17' C21' S22 C21 -44.9(8)
C25 C21' S22 C21 68.4(8)
C21 S22 C23 O23 171.0(4)
C21' S22 C23 O23 -162.9(5)
C21 S22 C23 N24 -10.8(3)
C21' S22 C23 N24 15.4(5)
O23 C23 N24 C25 -178.9(4)
S22 C23 N24 C25 2.8(4)
C23 N24 C25 O25 -178.6(4)
C23 N24 C25 C21 8.9(5)
C23 N24 C25 C21' -23.7(6)
C17 C21 C25 O25 51.2(7)
S22 C21 C25 O25 171.8(4)
C17 C21 C25 N24 -136.2(5)
S22 C21 C25 N24 -15.6(5)
C17 C21 C25 C21' -47.3(7)
S22 C21 C25 C21' 73.3(7)
C17' C21' C25 O25 -55.6(12)
S22 C21' C25 O25 -172.7(4)
C17' C21' C25 N24 148.9(9)
S22 C21' C25 N24 31.7(7)
C17' C21' C25 C21 46.3(10)
S22 C21' C25 C21 -70.9(7)
C2 C3 C31 N32 120.8(3)
C2 C3 C31 C36 -61.5(5)
C36 C31 N32 C33 -0.8(5)
C3 C31 N32 C33 177.0(3)
C31 N32 C33 C34 1.0(6)
N32 C33 C34 C35 0.6(6)
N32 C33 C34 C37 -178.3(4)
C33 C34 C35 C36 -2.4(6)
C37 C34 C35 C36 176.5(4)
N32 C31 C36 C35 -1.0(6)
C3 C31 C36 C35 -178.7(3)
C34 C35 C36 C31 2.7(6)
C33 C34 C37 C38 15.3(7)
C35 C34 C37 C38 -163.6(4)
