#------------------------------------------------------------------------------
#$Date: 2016-03-31 09:56:13 +0300 (Thu, 31 Mar 2016) $
#$Revision: 180648 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/47/7224759.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_7224759
loop_
_publ_author_name
'Aitipamula, Srinivasulu'
'Wong, Annie B.H.'
'Chow, Pui Shan'
'Tan, Reginald B. H.'
_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'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_chemical_melting_point          437.33
_chemical_name_common            Oxaprozin
_chemical_name_systematic        Oxaprozin
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.3129(5)
_cell_length_b                   7.6460(3)
_cell_length_c                   36.7642(15)
_cell_measurement_temperature    100
_cell_volume                     2898.9(2)
_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    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Agilent Supernova G8910B'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            28497
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1232
_exptl_crystal_preparation       'Crystallization from 1,4-Dioxane'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,4-Dioxane'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0612
_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)+(0.0720P)²+2.4480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1579
_reflns_number_gt                3558
_reflns_number_total             4042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra01802e2.cif
_cod_data_source_block           OXP
_cod_original_cell_volume        2899.0(2)
_cod_database_code               7224759
_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:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C8(H8), C12(H12), C11(H11), C16(H16), C14(H14), C9(H9), C17(H17),
 C10(H10), C15(H15)
;
_olex2_exptl_crystal_mounting_method 'Glass fiber'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 '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_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.43397(10) 0.91366(15) 0.39174(3) 0.0191(2) Uani 1 d .
O3 O 0.60776(13) 0.69947(19) 0.51386(3) 0.0305(3) Uani 1 d .
N1 N 0.25909(13) 0.87584(18) 0.42562(3) 0.0191(3) Uani 1 d .
O2 O 0.75569(14) 0.5925(2) 0.47541(4) 0.0404(4) Uani 1 d .
C18 C 0.02783(15) 1.0160(2) 0.35363(4) 0.0191(3) Uani 1 d .
H18 H 0.0836 1.0861 0.3391 0.023 Uiso 1 calc R
C2 C 0.32747(14) 0.92805(19) 0.36880(4) 0.0151(3) Uani 1 d .
C13 C 0.07980(14) 0.91084(19) 0.38121(4) 0.0159(3) Uani 1 d .
C7 C 0.35862(14) 0.95795(18) 0.33044(4) 0.0149(3) Uani 1 d .
C8 C 0.47375(14) 1.0457(2) 0.32147(4) 0.0180(3) Uani 1 d .
H8 H 0.5292 1.0871 0.3402 0.022 Uiso 1 calc R
C3 C 0.21890(14) 0.90630(19) 0.38960(4) 0.0159(3) Uani 1 d .
C1 C 0.38496(15) 0.8832(2) 0.42523(4) 0.0198(3) Uani 1 d .
C12 C 0.27847(14) 0.8968(2) 0.30244(4) 0.0176(3) Uani 1 d .
H12 H 0.2008 0.8359 0.3082 0.021 Uiso 1 calc R
C11 C 0.31223(16) 0.9249(2) 0.26628(4) 0.0228(3) Uani 1 d .
H11 H 0.2569 0.8844 0.2474 0.027 Uiso 1 calc R
C16 C -0.18802(16) 0.9151(3) 0.36831(5) 0.0280(4) Uani 1 d .
H16 H -0.2787 0.9157 0.3637 0.034 Uiso 1 calc R
C14 C -0.00492(15) 0.8107(2) 0.40245(4) 0.0193(3) Uani 1 d .
H14 H 0.0288 0.7409 0.4216 0.023 Uiso 1 calc R
C9 C 0.50696(16) 1.0720(2) 0.28531(4) 0.0236(3) Uani 1 d .
H9 H 0.5850 1.1316 0.2794 0.028 Uiso 1 calc R
C6 C 0.65091(17) 0.6575(2) 0.48109(4) 0.0255(3) Uani 1 d .
C17 C -0.10511(16) 1.0180(2) 0.34736(5) 0.0251(4) Uani 1 d .
H17 H -0.1397 1.0901 0.3287 0.030 Uiso 1 calc R
C10 C 0.42665(17) 1.0118(2) 0.25763(4) 0.0256(4) Uani 1 d .
H10 H 0.4498 1.0300 0.2329 0.031 Uiso 1 calc R
C15 C -0.13755(16) 0.8118(2) 0.39591(5) 0.0252(4) Uani 1 d .
H15 H -0.1937 0.7418 0.4103 0.030 Uiso 1 calc R
C4 C 0.47785(17) 0.8612(2) 0.45587(4) 0.0258(4) Uani 1 d .
H4A H 0.4300 0.8615 0.4792 0.031 Uiso 1 calc R
H4B H 0.5396 0.9603 0.4561 0.031 Uiso 1 calc R
C5 C 0.55178(19) 0.6908(3) 0.45196(5) 0.0333(4) Uani 1 d .
H5A H 0.4888 0.5931 0.4520 0.040 Uiso 1 calc R
H5B H 0.5961 0.6905 0.4281 0.040 Uiso 1 calc R
H3 H 0.664(4) 0.650(6) 0.5328(12) 0.118(15) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 C2 105.73(12)
C6 O3 H3 111(3)
C1 N1 C3 106.06(12)
C13 C18 H18 119.9
C17 C18 H18 119.9
C17 C18 C13 120.26(15)
O1 C2 C7 115.06(12)
C3 C2 O1 107.36(12)
C3 C2 C7 137.57(13)
C18 C13 C3 122.67(13)
C14 C13 C18 118.62(14)
C14 C13 C3 118.68(14)
C8 C7 C2 119.14(13)
C12 C7 C2 121.76(13)
C12 C7 C8 119.08(13)
C7 C8 H8 119.9
C9 C8 C7 120.25(15)
C9 C8 H8 119.9
N1 C3 C13 119.32(13)
C2 C3 N1 107.80(13)
C2 C3 C13 132.88(14)
O1 C1 C4 117.93(14)
N1 C1 O1 113.04(13)
N1 C1 C4 129.02(14)
C7 C12 H12 119.9
C11 C12 C7 120.22(14)
C11 C12 H12 119.9
C12 C11 H11 119.8
C12 C11 C10 120.31(15)
C10 C11 H11 119.8
C17 C16 H16 120.2
C15 C16 H16 120.2
C15 C16 C17 119.69(15)
C13 C14 H14 119.5
C15 C14 C13 120.98(15)
C15 C14 H14 119.5
C8 C9 H9 119.8
C8 C9 C10 120.40(15)
C10 C9 H9 119.8
O3 C6 C5 112.27(15)
O2 C6 O3 123.93(16)
O2 C6 C5 123.72(16)
C18 C17 C16 120.45(16)
C18 C17 H17 119.8
C16 C17 H17 119.8
C11 C10 H10 120.1
C9 C10 C11 119.73(15)
C9 C10 H10 120.1
C16 C15 C14 119.98(16)
C16 C15 H15 120.0
C14 C15 H15 120.0
C1 C4 H4A 109.6
C1 C4 H4B 109.6
C1 C4 C5 110.41(14)
H4A C4 H4B 108.1
C5 C4 H4A 109.6
C5 C4 H4B 109.6
C6 C5 C4 114.85(15)
C6 C5 H5A 108.6
C6 C5 H5B 108.6
C4 C5 H5A 108.6
C4 C5 H5B 108.6
H5A C5 H5B 107.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3891(17)
O1 C1 1.3511(18)
O3 C6 1.324(2)
O3 H3 0.98(5)
N1 C3 1.4069(18)
N1 C1 1.299(2)
O2 C6 1.208(2)
C18 H18 0.9500
C18 C13 1.401(2)
C18 C17 1.390(2)
C2 C7 1.464(2)
C2 C3 1.366(2)
C13 C3 1.468(2)
C13 C14 1.400(2)
C7 C8 1.403(2)
C7 C12 1.401(2)
C8 H8 0.9500
C8 C9 1.387(2)
C1 C4 1.488(2)
C12 H12 0.9500
C12 C11 1.391(2)
C11 H11 0.9500
C11 C10 1.391(2)
C16 H16 0.9500
C16 C17 1.394(3)
C16 C15 1.387(3)
C14 H14 0.9500
C14 C15 1.389(2)
C9 H9 0.9500
C9 C10 1.391(2)
C6 C5 1.502(2)
C17 H17 0.9500
C10 H10 0.9500
C15 H15 0.9500
C4 H4A 0.9900
C4 H4B 0.9900
C4 C5 1.516(3)
C5 H5A 0.9900
C5 H5B 0.9900
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
O1 C2 C7 C8 -28.61(19)
O1 C2 C7 C12 149.47(14)
O1 C2 C3 N1 -0.80(16)
O1 C2 C3 C13 178.59(15)
O1 C1 C4 C5 -69.5(2)
O3 C6 C5 C4 42.1(2)
N1 C1 C4 C5 109.8(2)
O2 C6 C5 C4 -141.0(2)
C18 C13 C3 N1 148.36(14)
C18 C13 C3 C2 -31.0(2)
C18 C13 C14 C15 1.5(2)
C2 O1 C1 N1 0.42(17)
C2 O1 C1 C4 179.85(14)
C2 C7 C8 C9 178.50(14)
C2 C7 C12 C11 -178.85(14)
C13 C18 C17 C16 -0.3(2)
C13 C14 C15 C16 -0.9(2)
C7 C2 C3 N1 177.88(17)
C7 C2 C3 C13 -2.7(3)
C7 C8 C9 C10 0.0(2)
C7 C12 C11 C10 0.8(2)
C8 C7 C12 C11 -0.8(2)
C8 C9 C10 C11 0.1(3)
C3 N1 C1 O1 -0.91(18)
C3 N1 C1 C4 179.74(16)
C3 C2 C7 C8 152.78(18)
C3 C2 C7 C12 -29.1(3)
C3 C13 C14 C15 179.30(14)
C1 O1 C2 C7 -178.75(13)
C1 O1 C2 C3 0.27(16)
C1 N1 C3 C2 1.04(17)
C1 N1 C3 C13 -178.44(13)
C1 C4 C5 C6 178.58(16)
C12 C7 C8 C9 0.4(2)
C12 C11 C10 C9 -0.5(3)
C14 C13 C3 N1 -29.4(2)
C14 C13 C3 C2 151.30(16)
C17 C18 C13 C3 -178.60(14)
C17 C18 C13 C14 -0.9(2)
C17 C16 C15 C14 -0.3(3)
C15 C16 C17 C18 0.9(3)
