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_7120782
_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         'C17 H18 N2 O6, C6 H6 N2 O'
_chemical_formula_sum            'C23 H24 N4 O7'
_chemical_formula_weight         468.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 90.080(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9427(16)
_cell_length_b                   12.732(3)
_cell_length_c                   22.382(4)
_cell_measurement_reflns_used    2358
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.72
_cell_volume                     2263.4(8)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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  0.0516
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16009
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.688
_diffrn_reflns_theta_min         1.820
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0795 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.8361. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5263
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0570
_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^)+(0.1057P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.2000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2754
_reflns_number_total             5263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc06992h2.cif
_cod_data_source_block           mo_2016393_0ma
_cod_database_code               7120782
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N2, C17
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
N2 \\sim C17: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C20(H20), C13(H13), C21(H21), C23(H23), C14(H14), C16(H16), C15(H15),
 C22(H22)
4.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
4.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'