Novel solid forms of oxaprozin: cocrystals and an extended release drug-drug salt of salbutamol
Aitipamula, Srinivasulu; Wong, Annie B.H.; Chow, Pui Shan; Tan, Reginald B. H.; RSC Adv.  (2016) –; doi:10.1039/C6RA01802E

data_7224754
_publ_section_title
;
 Novel solid forms of oxaprozin: cocrystals and an extended release
 drug-drug salt of salbutamol
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA01802E
_journal_year                    2016
_chemical_formula_moiety         'C18 H15 N O3, C6 H6 N'
_chemical_formula_sum            'C24 H21 N2 O3'
_chemical_formula_weight         385.43
_chemical_melting_point          407.5
_chemical_name_common            Oxaprozin-1,2-bis(4-pyridyl)ethane
_chemical_name_systematic
'1:0.5 Cocrystal of Oxaprozin and 1,2-bis(4-pyridyl)ethane'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2015-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-05-04 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                76.50(3)
_cell_angle_beta                 68.03(3)
_cell_angle_gamma                66.04(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7069(19)
_cell_length_b                   10.878(2)
_cell_length_c                   10.907(2)
_cell_measurement_reflns_used    3080
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.9451
_cell_measurement_theta_min      2.0229
_cell_volume                     971.5(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
????
;
_diffrn_ambient_temperature      110.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0235
_diffrn_orient_matrix_UB_12      -0.1072
_diffrn_orient_matrix_UB_13      0.0453
_diffrn_orient_matrix_UB_21      -0.0856
_diffrn_orient_matrix_UB_22      0.0501
_diffrn_orient_matrix_UB_23      -0.0195
_diffrn_orient_matrix_UB_31      0.0263
_diffrn_orient_matrix_UB_32      -0.0114
_diffrn_orient_matrix_UB_33      -0.0951
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13713
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.62
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'R. H. Blessing, Acta Cryst. 1995 A51, 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             406
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.44
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0505
_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/[\s^2^(Fo^2^)+(0.0766P)^2^+0.3623P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                4067
_reflns_number_total             4686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra01802e2.cif
_cod_data_source_block           OXP-BPE
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7224754
_diffrn_number_total             5409
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C14(H14), C8(H8), C12(H12), C16(H16), C15(H15), C9(H9), C11(H11),
 C17(H17), C10(H10), C20(H20), C23(H23), C19(H19), C22(H22)
;