#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/47/7224754.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_7224754
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, 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/[σ²(Fo²)+(0.0766P)²+0.3623P] where P=(Fo²+2Fc²)/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)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_refinement_flags_posn
O2 O -0.12458(12) 0.67766(11) 0.44794(10) 0.0272(2) Uani 1 d .
N1 N 0.50960(12) 0.51222(11) 0.29145(10) 0.0182(2) Uani 1 d .
O1 O 0.40018(11) 0.42704(10) 0.20274(10) 0.0251(2) Uani 1 d .
O3 O -0.14364(12) 0.81303(12) 0.26130(11) 0.0343(3) Uani 1 d .
N2 N 0.54556(14) 0.89172(13) 0.37212(12) 0.0279(3) Uani 1 d .
C13 C 0.79684(15) 0.39541(13) 0.18881(12) 0.0190(3) Uani 1 d .
C7 C 0.62059(15) 0.25531(13) 0.06870(12) 0.0195(3) Uani 1 d .
C18 C 0.91984(15) 0.34328(14) 0.07503(13) 0.0211(3) Uani 1 d .
H18 H 0.8962 0.3234 0.0065 0.025 Uiso 1 calc R
C14 C 0.83389(16) 0.42662(13) 0.28739(13) 0.0215(3) Uani 1 d .
H14 H 0.7513 0.4656 0.3635 0.026 Uiso 1 calc R
C8 C 0.54060(16) 0.26852(14) -0.02009(13) 0.0225(3) Uani 1 d .
H8 H 0.4548 0.3495 -0.0286 0.027 Uiso 1 calc R
C12 C 0.74697(16) 0.13542(13) 0.07938(13) 0.0217(3) Uani 1 d .
H12 H 0.8021 0.1252 0.1392 0.026 Uiso 1 calc R
C16 C 1.11193(16) 0.34760(14) 0.16182(14) 0.0239(3) Uani 1 d .
H16 H 1.2191 0.3298 0.1535 0.029 Uiso 1 calc R
C5 C 0.11301(15) 0.67161(14) 0.26489(13) 0.0214(3) Uani 1 d .
H5A H 0.1439 0.7502 0.2161 0.026 Uiso 1 calc R
H5B H 0.1369 0.6111 0.1987 0.026 Uiso 1 calc R
C6 C -0.06355(15) 0.72083(13) 0.33631(13) 0.0214(3) Uani 1 d .
C15 C 0.99049(17) 0.40101(14) 0.27454(14) 0.0240(3) Uani 1 d .
H15 H 1.0149 0.4200 0.3431 0.029 Uiso 1 calc R
C9 C 0.58615(17) 0.16389(15) -0.09553(14) 0.0271(3) Uani 1 d .
H9 H 0.5314 0.1735 -0.1554 0.032 Uiso 1 calc R
C11 C 0.79237(17) 0.03143(14) 0.00335(14) 0.0250(3) Uani 1 d .
H11 H 0.8788 -0.0494 0.0108 0.030 Uiso 1 calc R
C2 C 0.56399(15) 0.36353(13) 0.15379(12) 0.0199(3) Uani 1 d .
C3 C 0.63139(15) 0.41730(13) 0.20670(13) 0.0202(3) Uani 1 d .
C17 C 1.07610(16) 0.32040(14) 0.06133(14) 0.0232(3) Uani 1 d .
H17 H 1.1586 0.2861 -0.0168 0.028 Uiso 1 calc R
C4 C 0.21331(15) 0.59585(14) 0.35721(13) 0.0231(3) Uani 1 d .
H4A H 0.2178 0.6618 0.4033 0.028 Uiso 1 calc R
H4B H 0.1621 0.5363 0.4255 0.028 Uiso 1 calc R
C1 C 0.37738(16) 0.51301(14) 0.28399(13) 0.0229(3) Uani 1 d .
C21 C 0.21544(16) 0.97030(15) 0.48537(14) 0.0257(3) Uani 1 d .
C10 C 0.71160(18) 0.04524(15) -0.08386(14) 0.0278(3) Uani 1 d .
H10 H 0.7423 -0.0264 -0.1353 0.033 Uiso 1 calc R
C20 C 0.28585(17) 1.05578(15) 0.39210(15) 0.0278(3) Uani 1 d .
H20 H 0.2221 1.1434 0.3654 0.033 Uiso 1 calc R
C23 C 0.47873(19) 0.80921(17) 0.46257(17) 0.0350(4) Uani 1 d .
H23 H 0.5456 0.7227 0.4883 0.042 Uiso 1 calc R
C19 C 0.44931(17) 1.01299(15) 0.33807(15) 0.0277(3) Uani 1 d .
H19 H 0.4953 1.0727 0.2737 0.033 Uiso 1 calc R
C22 C 0.31607(19) 0.84437(17) 0.52043(16) 0.0342(4) Uani 1 d .
H22 H 0.2733 0.7824 0.5841 0.041 Uiso 1 calc R
C24 C 0.03733(17) 1.0115(2) 0.54408(16) 0.0366(4) Uani 1 d .
H24A H -0.0086 1.1084 0.5588 0.044 Uiso 1 calc R
H24B H 0.0109 0.9592 0.6315 0.044 Uiso 1 calc R
H3 H -0.273(3) 0.840(3) 0.313(3) 0.069(7) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C3 105.27(11) . .
C1 O1 C2 105.41(11) . .
C6 O3 H3 110.1(13) . .
C23 N2 C19 117.57(13) . .
C18 C13 C14 118.79(12) . .
C18 C13 C3 121.48(12) . .
C14 C13 C3 119.73(12) . .
C8 C7 C2 119.44(12) . .
C12 C7 C8 118.94(12) . .
C12 C7 C2 121.51(12) . .
C13 C18 H18 119.7 . .
C17 C18 C13 120.60(12) . .
C17 C18 H18 119.7 . .
C13 C14 H14 119.8 . .
C15 C14 C13 120.38(13) . .
C15 C14 H14 119.8 . .
C7 C8 H8 119.8 . .
C9 C8 C7 120.34(13) . .
C9 C8 H8 119.8 . .
C7 C12 H12 119.8 . .
C11 C12 C7 120.46(13) . .
C11 C12 H12 119.8 . .
C15 C16 H16 120.1 . .
C17 C16 H16 120.1 . .
C17 C16 C15 119.81(12) . .
H5A C5 H5B 107.7 . .
C6 C5 H5A 108.8 . .
C6 C5 H5B 108.8 . .
C6 C5 C4 113.66(11) . .
C4 C5 H5A 108.8 . .
C4 C5 H5B 108.8 . .
O2 C6 O3 124.10(13) . .
O2 C6 C5 123.95(12) . .
O3 C6 C5 111.91(12) . .
C14 C15 C16 120.30(12) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C8 C9 H9 119.9 . .
C8 C9 C10 120.19(13) . .
C10 C9 H9 119.9 . .
C12 C11 H11 119.9 . .
C12 C11 C10 120.14(13) . .
C10 C11 H11 119.9 . .
O1 C2 C7 116.25(11) . .
C3 C2 O1 107.48(11) . .
C3 C2 C7 136.16(12) . .
N1 C3 C13 119.00(12) . .
C2 C3 N1 108.17(11) . .
C2 C3 C13 132.82(12) . .
C18 C17 C16 120.06(13) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C5 C4 H4A 109.2 . .
C5 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C1 C4 C5 112.02(11) . .
C1 C4 H4A 109.2 . .
C1 C4 H4B 109.2 . .
N1 C1 O1 113.66(12) . .
N1 C1 C4 126.57(12) . .
O1 C1 C4 119.77(12) . .
C20 C21 C22 116.97(13) . .
C20 C21 C24 121.43(15) . .
C22 C21 C24 121.59(15) . .
C9 C10 C11 119.92(13) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
C21 C20 H20 120.1 . .
C19 C20 C21 119.70(14) . .
C19 C20 H20 120.1 . .
N2 C23 H23 118.6 . .
N2 C23 C22 122.73(15) . .
C22 C23 H23 118.6 . .
N2 C19 C20 123.08(14) . .
N2 C19 H19 118.5 . .
C20 C19 H19 118.5 . .
C21 C22 H22 120.0 . .
C23 C22 C21 119.94(15) . .
C23 C22 H22 120.0 . .
C21 C24 C24 112.63(16) . 2_576
C21 C24 H24A 109.1 . .
C21 C24 H24B 109.1 . .
C24 C24 H24A 109.1 2_576 .
C24 C24 H24B 109.1 2_576 .
H24A C24 H24B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C6 1.2136(17) .
N1 C3 1.3982(17) .
N1 C1 1.3126(17) .
O1 C2 1.3912(16) .
O1 C1 1.3346(17) .
O3 C6 1.3188(17) .
O3 H3 1.11(3) .
N2 C23 1.334(2) .
N2 C19 1.335(2) .
C13 C18 1.3990(18) .
C13 C14 1.3998(18) .
C13 C3 1.4665(18) .
C7 C8 1.4030(18) .
C7 C12 1.3986(19) .
C7 C2 1.4670(19) .
C18 H18 0.9500 .
C18 C17 1.3879(19) .
C14 H14 0.9500 .
C14 C15 1.3867(19) .
C8 H8 0.9500 .
C8 C9 1.387(2) .
C12 H12 0.9500 .
C12 C11 1.3861(19) .
C16 H16 0.9500 .
C16 C15 1.390(2) .
C16 C17 1.3892(19) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5 C6 1.5104(18) .
C5 C4 1.5282(18) .
C15 H15 0.9500 .
C9 H9 0.9500 .
C9 C10 1.388(2) .
C11 H11 0.9500 .
C11 C10 1.392(2) .
C2 C3 1.3617(19) .
C17 H17 0.9500 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C1 1.4849(19) .
C21 C20 1.386(2) .
C21 C22 1.387(2) .
C21 C24 1.509(2) .
C10 H10 0.9500 .
C20 H20 0.9500 .
C20 C19 1.382(2) .
C23 H23 0.9500 .
C23 C22 1.384(2) .
C19 H19 0.9500 .
C22 H22 0.9500 .
C24 C24 1.514(3) 2_576
C24 H24A 0.9900 .
C24 H24B 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
_geom_torsion_site_symmetry_4
O1 C2 C3 N1 1.45(14) .
O1 C2 C3 C13 -177.34(13) .
N2 C23 C22 C21 -0.4(3) .
C13 C18 C17 C16 0.8(2) .
C13 C14 C15 C16 1.8(2) .
C7 C8 C9 C10 -0.1(2) .
C7 C12 C11 C10 -0.4(2) .
C7 C2 C3 N1 -174.31(14) .
C7 C2 C3 C13 6.9(3) .
C18 C13 C14 C15 -2.6(2) .
C18 C13 C3 N1 -156.30(12) .
C18 C13 C3 C2 22.4(2) .
C14 C13 C18 C17 1.3(2) .
C14 C13 C3 N1 23.92(18) .
C14 C13 C3 C2 -157.40(15) .
C8 C7 C12 C11 0.0(2) .
C8 C7 C2 O1 37.25(17) .
C8 C7 C2 C3 -147.26(16) .
C8 C9 C10 C11 -0.3(2) .
C12 C7 C8 C9 0.2(2) .
C12 C7 C2 O1 -138.92(13) .
C12 C7 C2 C3 36.6(2) .
C12 C11 C10 C9 0.5(2) .
C5 C4 C1 N1 129.67(14) .
C5 C4 C1 O1 -51.65(17) .
C6 C5 C4 C1 161.95(12) .
C15 C16 C17 C18 -1.6(2) .
C2 O1 C1 N1 0.56(15) .
C2 O1 C1 C4 -178.28(12) .
C2 C7 C8 C9 -176.04(12) .
C2 C7 C12 C11 176.22(12) .
C3 N1 C1 O1 0.31(15) .
C3 N1 C1 C4 179.06(13) .
C3 C13 C18 C17 -178.52(12) .
C3 C13 C14 C15 177.19(12) .
C17 C16 C15 C14 0.3(2) .
C4 C5 C6 O2 -18.04(19) .
C4 C5 C6 O3 164.02(12) .
C1 N1 C3 C13 177.89(12) .
C1 N1 C3 C2 -1.09(14) .
C1 O1 C2 C7 175.49(11) .
C1 O1 C2 C3 -1.23(14) .
C21 C20 C19 N2 -0.6(2) .
C20 C21 C22 C23 -0.1(2) .
C20 C21 C24 C24 82.7(2) 2_576
C23 N2 C19 C20 0.1(2) .
C19 N2 C23 C22 0.4(2) .
C22 C21 C20 C19 0.6(2) .
C22 C21 C24 C24 -96.1(2) 2_576
C24 C21 C20 C19 -178.31(13) .
C24 C21 C22 C23 178.76(15) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139201876
