#------------------------------------------------------------------------------
#$Date: 2016-08-26 16:24:54 +0300 (Fri, 26 Aug 2016) $
#$Revision: 186020 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119162.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_7119162
loop_
_publ_author_name
'Lynne H. Thomas'
'Craig Wales'
'Chick C. Wilson'
_publ_section_title
;
 Selective preparation of elusive and alternative single component
 polymorphic solid forms through multi-component crystallisation routes
;
_journal_name_full               Chem.Commun.
_journal_page_first              7372
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C15 H13 N3 O4 S'
_chemical_formula_sum            'C15 H13 N3 O4 S'
_chemical_formula_weight         331.34
_chemical_name_systematic        piroxicam
_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
_audit_update_record
;
2016-02-01 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                80.602(2)
_cell_angle_beta                 68.952(2)
_cell_angle_gamma                69.742(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8557(3)
_cell_length_b                   10.1043(4)
_cell_length_c                   10.4713(5)
_cell_measurement_reflns_used    16529
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61.15
_cell_measurement_theta_min      1
_cell_volume                     727.01(5)
_computing_cell_refinement       'Bruker APEX2 (2009)'
_computing_data_collection       'Bruker APEX2 (2009)'
_computing_data_reduction        'Bruker APEX2 (2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'CCD; rotation images'
_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  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16541
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Blessing, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0477P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                3102
_reflns_number_total             4375
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc01027j2.cif
_cod_data_source_block           shelxl_2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7119162
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 0.388(2) 0.4573(18) 0.3851(19) 0.019(5) Uiso 1 1 d . . .
H2 H 0.250(3) 0.607(2) 1.008(2) 0.028(5) Uiso 1 1 d . . .
H9 H 0.177(3) 0.213(2) 0.417(2) 0.035(6) Uiso 1 1 d . . .
H3 H 0.371(3) 0.3710(19) 1.076(2) 0.027(5) Uiso 1 1 d . . .
H11 H 0.207(2) -0.2751(17) 0.3103(18) 0.013(4) Uiso 1 1 d . . .
H10 H 0.244(2) -0.1463(17) 0.4669(19) 0.016(4) Uiso 1 1 d . . .
H4 H 0.402(3) 0.1877(18) 0.9550(19) 0.020(5) Uiso 1 1 d . . .
H1 H 0.138(3) 0.654(2) 0.815(2) 0.027(5) Uiso 1 1 d . . .
H7 H 0.478(3) 0.2863(19) 0.384(2) 0.025(5) Uiso 1 1 d . . .
H12 H 0.131(3) -0.1489(19) 0.114(2) 0.026(5) Uiso 1 1 d . . .
H5 H 0.511(3) 0.3797(18) 0.4807(19) 0.026(5) Uiso 1 1 d . . .
H8 H 0.314(3) 0.011(2) 0.750(3) 0.057(8) Uiso 1 1 d . . .
H13 H 0.107(3) 0.0927(18) 0.0771(19) 0.020(5) Uiso 1 1 d . . .
S1 S 0.10345(5) 0.48134(4) 0.64541(4) 0.01435(10) Uani 1 1 d . . .
O1 O 0.30517(15) -0.02774(11) 0.60096(12) 0.0168(2) Uani 1 1 d . . .
O2 O 0.31423(17) 0.06435(12) 0.80968(12) 0.0191(2) Uani 1 1 d . . .
N1 N 0.24278(17) 0.34877(12) 0.54512(13) 0.0135(3) Uani 1 1 d . . .
O3 O -0.08463(15) 0.46633(11) 0.70252(12) 0.0183(2) Uani 1 1 d . . .
O4 O 0.12639(16) 0.60977(11) 0.57048(12) 0.0187(2) Uani 1 1 d . . .
N2 N 0.21808(19) 0.13009(14) 0.43372(14) 0.0148(3) Uani 1 1 d . . .
C8 C 0.2657(2) 0.21239(15) 0.61662(16) 0.0138(3) Uani 1 1 d . . .
C12 C 0.2171(2) -0.10081(16) 0.38256(17) 0.0168(3) Uani 1 1 d . . .
C10 C 0.2648(2) 0.09536(16) 0.54980(16) 0.0144(3) Uani 1 1 d . . .
C7 C 0.2883(2) 0.19138(16) 0.74243(16) 0.0151(3) Uani 1 1 d . . .
N3 N 0.1578(2) 0.11253(14) 0.24002(14) 0.0185(3) Uani 1 1 d . . .
C11 C 0.1989(2) 0.04247(16) 0.35110(16) 0.0148(3) Uani 1 1 d . . .
C1 C 0.2027(2) 0.44796(16) 0.77797(16) 0.0154(3) Uani 1 1 d . . .
C6 C 0.2792(2) 0.30656(16) 0.81758(16) 0.0152(3) Uani 1 1 d . . .
C3 C 0.2576(2) 0.52844(18) 0.95769(18) 0.0214(3) Uani 1 1 d . . .
C2 C 0.1932(2) 0.55976(17) 0.84556(17) 0.0184(3) Uani 1 1 d . . .
C4 C 0.3314(2) 0.38885(19) 0.99996(18) 0.0206(3) Uani 1 1 d . . .
C14 C 0.1520(2) -0.10403(18) 0.17690(18) 0.0206(3) Uani 1 1 d . . .
C15 C 0.1938(2) -0.17406(17) 0.29239(18) 0.0189(3) Uani 1 1 d . . .
C5 C 0.3444(2) 0.27843(18) 0.93037(17) 0.0182(3) Uani 1 1 d . . .
C9 C 0.4210(2) 0.36762(17) 0.44048(18) 0.0178(3) Uani 1 1 d . . .
C13 C 0.1345(2) 0.03881(18) 0.15551(18) 0.0203(3) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
O3 S1 O4 119.23(7) . .
O3 S1 N1 107.93(7) . .
O4 S1 N1 108.14(7) . .
O3 S1 C1 107.92(7) . .
O4 S1 C1 109.67(7) . .
N1 S1 C1 102.69(7) . .
C7 O2 H8 101.4(15) . .
C8 N1 C9 115.15(11) . .
C8 N1 S1 113.57(10) . .
C9 N1 S1 116.65(10) . .
C10 N2 C11 128.85(14) . .
C10 N2 H9 115.7(15) . .
C11 N2 H9 114.5(15) . .
C7 C8 N1 121.33(13) . .
C7 C8 C10 120.58(13) . .
N1 C8 C10 118.10(13) . .
C15 C12 C11 117.74(15) . .
C15 C12 H10 122.0(10) . .
C11 C12 H10 120.3(10) . .
O1 C10 N2 123.70(14) . .
O1 C10 C8 120.14(14) . .
N2 C10 C8 116.16(13) . .
O2 C7 C8 122.36(14) . .
O2 C7 C6 114.75(14) . .
C8 C7 C6 122.86(14) . .
C13 N3 C11 117.03(14) . .
N3 C11 C12 123.70(15) . .
N3 C11 N2 112.40(13) . .
C12 C11 N2 123.89(14) . .
C2 C1 C6 122.12(15) . .
C2 C1 S1 120.22(12) . .
C6 C1 S1 117.54(12) . .
C5 C6 C1 118.20(15) . .
C5 C6 C7 121.41(14) . .
C1 C6 C7 120.39(14) . .
C2 C3 C4 120.48(15) . .
C2 C3 H2 119.6(11) . .
C4 C3 H2 120.0(11) . .
C3 C2 C1 118.30(15) . .
C3 C2 H1 123.2(12) . .
C1 C2 H1 118.5(12) . .
C5 C4 C3 120.85(16) . .
C5 C4 H3 120.4(12) . .
C3 C4 H3 118.7(12) . .
C15 C14 C13 118.38(16) . .
C15 C14 H12 122.7(11) . .
C13 C14 H12 118.9(11) . .
C14 C15 C12 119.54(15) . .
C14 C15 H11 120.3(10) . .
C12 C15 H11 120.1(10) . .
C4 C5 C6 120.03(16) . .
C4 C5 H4 119.7(11) . .
C6 C5 H4 120.1(12) . .
N1 C9 H6 109.7(10) . .
N1 C9 H7 106.3(11) . .
H6 C9 H7 111.2(15) . .
N1 C9 H5 113.2(11) . .
H6 C9 H5 104.0(13) . .
H7 C9 H5 112.6(15) . .
N3 C13 C14 123.60(16) . .
N3 C13 H13 114.3(11) . .
C14 C13 H13 122.1(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.4334(11) .
S1 O4 1.4353(11) .
S1 N1 1.6473(13) .
S1 C1 1.7581(16) .
O1 C10 1.2514(18) .
O2 C7 1.3460(18) .
O2 H8 0.88(3) .
N1 C8 1.4422(18) .
N1 C9 1.487(2) .
N2 C10 1.352(2) .
N2 C11 1.4112(19) .
N2 H9 0.805(19) .
C8 C7 1.365(2) .
C8 C10 1.472(2) .
C12 C15 1.386(2) .
C12 C11 1.400(2) .
C12 H10 0.985(18) .
C7 C6 1.477(2) .
N3 C13 1.341(2) .
N3 C11 1.342(2) .
C1 C2 1.396(2) .
C1 C6 1.402(2) .
C6 C5 1.400(2) .
C3 C2 1.389(2) .
C3 C4 1.391(2) .
C3 H2 1.00(2) .
C2 H1 0.958(18) .
C4 C5 1.385(2) .
C4 H3 0.92(2) .
C14 C15 1.384(2) .
C14 C13 1.390(2) .
C14 H12 0.95(2) .
C15 H11 0.982(16) .
C5 H4 0.912(17) .
C9 H6 0.998(17) .
C9 H7 0.970(19) .
C9 H5 0.989(19) .
C13 H13 0.959(18) .
