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_7224755
_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         'C13 H22 N O3, C18 H14 N O3'
_chemical_formula_sum            'C31 H36 N2 O6'
_chemical_formula_weight         532.62
_chemical_melting_point          445.67
_chemical_name_common            Oxaprozin-Salbutamol
_chemical_name_systematic        '1:1 Salt of Oxaprozin and Salbutamol'
_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                76.02(3)
_cell_angle_beta                 69.82(3)
_cell_angle_gamma                88.05(3)
_cell_formula_units_Z            2
_cell_length_a                   10.453(2)
_cell_length_b                   10.627(2)
_cell_length_c                   13.379(3)
_cell_measurement_reflns_used    2963
_cell_measurement_temperature    110.1500
_cell_measurement_theta_max      30.9628
_cell_measurement_theta_min      2.1689
_cell_volume                     1351.7(6)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0249
_diffrn_orient_matrix_UB_12      0.0954
_diffrn_orient_matrix_UB_13      -0.0264
_diffrn_orient_matrix_UB_21      -0.0058
_diffrn_orient_matrix_UB_22      -0.0192
_diffrn_orient_matrix_UB_23      -0.0950
_diffrn_orient_matrix_UB_31      -0.0779
_diffrn_orient_matrix_UB_32      -0.0030
_diffrn_orient_matrix_UB_33      0.0259
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19414
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.17
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0786
_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/[\s^2^(Fo^2^)+(0.0837P)^2^+0.7199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.1956
_reflns_number_gt                6008
_reflns_number_total             6617
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra01802e2.cif
_cod_data_source_block           OXP-SAL
_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               7224755
_diffrn_number_total             7716
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C4(H4A,H4B), C25(H25A,H25B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C21(H21), C20(H20), C18(H18), C14(H14), C11(H11), C12(H12),
 C17(H17), C10(H10), C8(H8), C15(H15), C9(H9), C16(H16)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;