Taming photo-induced oxidation degradation of dihydropyridine drugs through cocrystallization
Yu, Qihui; Yan, zhicheng; Bao, junjie; Wang, Jian-Rong; Mei, Xuefeng; Chem. Commun.  (2017) –; doi:10.1039/C7CC06992H

data_7120784
_publ_section_title
;
 Taming photo-induced oxidation degradation of dihydropyridine drugs
 through cocrystallization
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06992H
_journal_year                    2017
_chemical_formula_moiety         'C6 H6 N2 O, C17 H18 N2 O6'
_chemical_formula_sum            'C23 H24 N4 O7'
_chemical_formula_weight         468.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_audit_update_record
;
2017-09-06 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8608(9)
_cell_length_b                   12.3313(14)
_cell_length_c                   22.699(3)
_cell_measurement_reflns_used    5093
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.110
_cell_measurement_theta_min      2.742
_cell_volume                     2200.3(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18657
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_min         1.794
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0894 before and 0.0589 after correction. The Ratio of minimum to maximum transmission is 0.8011. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0616P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4395
_reflns_number_total             5183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06992h2.cif
_cod_data_source_block           mo_2016560_0m
_cod_original_cell_volume        2200.3(4)
_cod_database_code               7120784
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.2(12)
 -0.2(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H1 of N1
 At 1.5 times of:
  All C(H,H) groups, H3A of N3, All C(H,H,H) groups
3. Restrained distances
 C6-H6A
 0.85 with sigma of 0.01
 C6-H6B
 0.85 with sigma of 0.01
 H6A-H6B
 1.388291 with sigma of 0.03
 C7-C5 \\sim C6-C1
 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C9(H9), N1(H1), C20(H20), C21(H21), C12(H12)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'