#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:04:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180528 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/97/7219754.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7219754
loop_
_publ_author_name
'Upadhyay, Pratik P.'
'Bond, Andrew D.'
_publ_section_title
;
 Crystallization and disorder of the polytypic α1and α2polymorphs of
 piroxicam
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              5266
_journal_paper_doi               10.1039/C5CE00050E
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H13 N3 O4 S'
_chemical_formula_sum            'C15 H13 N3 O4 S'
_chemical_formula_weight         331.34
_chemical_name_common            'Piroxicam: Form Alpha1'
_chemical_name_systematic        Piroxicam
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2b'
_space_group_name_H-M_alt        'P b c 21'
_symmetry_space_group_name_Hall  'P 2c -2b'
_symmetry_space_group_name_H-M   'P b c 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-02-23 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3964(14)
_cell_length_b                   11.7965(10)
_cell_length_c                   6.9851(5)
_cell_measurement_reflns_used    2039
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      50.03
_cell_measurement_theta_min      2.54
_cell_volume                     1433.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.485
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.485
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3586
_diffrn_reflns_point_group_measured_fraction_full 0.364
_diffrn_reflns_point_group_measured_fraction_max 0.635
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         50.437
_diffrn_reflns_theta_min         7.639
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    2.250
_exptl_absorpt_correction_T_max  0.7500
_exptl_absorpt_correction_T_min  0.5468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
Flack x determined using 190 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.11(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         949
_refine_ls_number_restraints     91
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²+2.1533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.373
_reflns_Friedel_fraction_full    0.219
_reflns_Friedel_fraction_max     0.389
_reflns_number_gt                743
_reflns_number_total             949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce00050e4.cif
_cod_data_source_block           alpha1
_cod_depositor_comments
'Adding full bibliography for 7219754--7219755.cif.'
_cod_database_code               7219754
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.806
_shelx_estimated_absorpt_t_max   0.936
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, z'
'x, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.3032(2) 0.4456(3) -0.0072(5) 0.0394(11) Uani 1 1 d . .
O1 O 0.3081(5) 0.3261(7) 0.0436(11) 0.045(3) Uani 1 1 d . .
O2 O 0.2777(5) 0.4790(7) -0.1935(12) 0.051(3) Uani 1 1 d . .
O3 O 0.1729(5) 0.7975(8) 0.1654(13) 0.046(3) Uani 1 1 d . .
O4 O 0.3196(5) 0.7996(8) 0.1148(13) 0.048(3) Uani 1 1 d . .
H1 H 0.2767 0.8272 0.1282 0.073 Uiso 1 1 calc R U
N1 N 0.2457(6) 0.5073(9) 0.1502(13) 0.029(3) Uani 1 1 d . .
N2 N 0.1119(8) 0.6260(10) 0.1548(16) 0.045(3) Uani 1 1 d . .
H2 H 0.1202 0.5549 0.1375 0.067 Uiso 1 1 calc R U
N3 N -0.0114(7) 0.5621(10) 0.1890(15) 0.044(3) Uani 1 1 d . .
C1 C 0.2468(10) 0.6288(13) 0.1358(18) 0.034(4) Uani 1 1 d . U
C2 C 0.3142(11) 0.6832(14) 0.1159(18) 0.038(4) Uani 1 1 d . U
C3 C 0.4569(10) 0.6839(13) 0.1124(18) 0.045(5) Uani 1 1 d . U
H3 H 0.4564 0.7599 0.1478 0.054 Uiso 1 1 calc R U
C4 C 0.5275(10) 0.6290(14) 0.0862(18) 0.049(5) Uani 1 1 d . U
H4 H 0.5734 0.6690 0.0947 0.058 Uiso 1 1 calc R U
C5 C 0.5273(10) 0.5158(14) 0.0480(18) 0.046(5) Uani 1 1 d . U
H5 H 0.5737 0.4769 0.0397 0.056 Uiso 1 1 calc R U
C6 C 0.4587(10) 0.4579(13) 0.0214(19) 0.045(4) Uani 1 1 d . U
H6 H 0.4589 0.3812 -0.0093 0.054 Uiso 1 1 calc R U
C7 C 0.3916(9) 0.5147(13) 0.0407(16) 0.033(4) Uani 1 1 d . U
C8 C 0.3879(11) 0.6278(14) 0.0868(16) 0.035(4) Uani 1 1 d . U
C9 C 0.2501(7) 0.4623(11) 0.3476(17) 0.044(4) Uani 1 1 d . U
H9A H 0.2158 0.5040 0.4288 0.067 Uiso 1 1 calc R U
H9B H 0.3017 0.4698 0.3945 0.067 Uiso 1 1 calc R U
H9C H 0.2358 0.3837 0.3476 0.067 Uiso 1 1 calc R U
C10 C 0.1751(11) 0.6930(16) 0.153(2) 0.047(5) Uani 1 1 d . U
C11 C 0.0324(10) 0.6574(13) 0.182(2) 0.038(4) Uani 1 1 d . U
C12 C 0.0059(8) 0.7657(13) 0.1896(16) 0.038(4) Uani 1 1 d . U
H12 H 0.0391 0.8271 0.1785 0.046 Uiso 1 1 calc R U
C13 C -0.0719(9) 0.7808(13) 0.214(2) 0.051(5) Uani 1 1 d . U
H13 H -0.0923 0.8533 0.2242 0.061 Uiso 1 1 calc R U
C14 C -0.1192(8) 0.6871(13) 0.2239(18) 0.044(4) Uani 1 1 d . U
H14 H -0.1720 0.6952 0.2393 0.053 Uiso 1 1 calc R U
C15 C -0.0864(10) 0.5823(13) 0.210(2) 0.047(4) Uani 1 1 d . U
H15 H -0.1189 0.5199 0.2167 0.057 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O2 S1 O1 120.5(5)
O2 S1 N1 107.2(5)
O1 S1 N1 107.4(5)
O2 S1 C7 108.3(6)
O1 S1 C7 110.4(7)
N1 S1 C7 101.3(7)
C2 O4 H1 109.5
C1 N1 C9 115.0(10)
C1 N1 S1 112.6(10)
C9 N1 S1 115.4(8)
C10 N2 C11 129.0(14)
C10 N2 H2 115.5
C11 N2 H2 115.5
C15 N3 C11 113.8(14)
C2 C1 N1 119.7(15)
C2 C1 C10 120.4(15)
N1 C1 C10 119.9(15)
C1 C2 O4 122.4(16)
C1 C2 C8 124.7(16)
O4 C2 C8 112.8(17)
C8 C3 C4 121.6(15)
C8 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 118.5(16)
C5 C4 H4 120.7
C3 C4 H4 120.7
C4 C5 C6 120.7(15)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 119.0(14)
C7 C6 H6 120.5
C5 C6 H6 120.5
C6 C7 C8 123.0(16)
C6 C7 S1 120.1(13)
C8 C7 S1 116.8(14)
C7 C8 C3 117.0(17)
C7 C8 C2 120.8(17)
C3 C8 C2 122.2(16)
N1 C9 H9A 109.5
N1 C9 H9B 109.5
H9A C9 H9B 109.5
N1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O3 C10 N2 123.8(17)
O3 C10 C1 123.2(17)
N2 C10 C1 113.0(15)
N3 C11 C12 126.0(15)
N3 C11 N2 109.2(13)
C12 C11 N2 124.7(14)
C11 C12 C13 117.3(15)
C11 C12 H12 121.3
C13 C12 H12 121.3
C12 C13 C14 119.3(14)
C12 C13 H13 120.3
C14 C13 H13 120.3
C15 C14 C13 118.2(14)
C15 C14 H14 120.9
C13 C14 H14 120.9
N3 C15 C14 125.3(15)
N3 C15 H15 117.3
C14 C15 H15 117.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.430(9)
S1 O1 1.456(8)
S1 N1 1.656(10)
S1 C7 1.773(14)
O3 C10 1.236(15)
O4 C2 1.377(14)
O4 H1 0.8200
N1 C1 1.437(16)
N1 C9 1.480(13)
N2 C10 1.354(17)
N2 C11 1.444(16)
N2 H2 0.8600
N3 C15 1.334(15)
N3 C11 1.358(15)
C1 C2 1.344(18)
C1 C10 1.46(2)
C2 C8 1.452(18)
C3 C8 1.383(17)
C3 C4 1.400(17)
C3 H3 0.9300
C4 C5 1.362(18)
C4 H4 0.9300
C5 C6 1.387(16)
C5 H5 0.9300
C6 C7 1.354(16)
C6 H6 0.9300
C7 C8 1.373(17)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C11 C12 1.359(17)
C12 C13 1.376(15)
C12 H12 0.9300
C13 C14 1.379(15)
C13 H13 0.9300
C14 C15 1.366(16)
C14 H14 0.9300
C15 H15 0.9300
