Comparison of the crystal structures and thermochemistry of a novel soluble guanylate cyclase stimulator riociguat and its solvates.
Zhou, Xinbo; Hu, Xiurong; Gu, Jianming; Zhu, Jianrong; Acta crystallographica Section B, Structural science, crystal engineering and materials 73 (2017) 891–898; doi:10.1107/S2052520617006011

data_2311714
_publ_section_title
;
 Comparison of the crystal structures and thermochemistry of a novel
 soluble guanylate cyclase stimulator riociguat and its solvates.
;
_journal_coeditor_code           AO5027
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              891
_journal_page_last               898
_journal_paper_doi               10.1107/S2052520617006011
_journal_volume                  73
_journal_year                    2017
_chemical_formula_moiety         'C20 H19 F N8 O2, 0.5(C3 H7 N O)'
_chemical_formula_sum            'C21.5 H22.5 F N8.5 O2.5'
_chemical_formula_weight         458.97
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                73.920(3)
_cell_angle_beta                 74.788(2)
_cell_angle_gamma                83.294(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6703(7)
_cell_length_b                   13.4220(9)
_cell_length_c                   16.9095(12)
_cell_measurement_reflns_used    10475
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     2242.9(3)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17506
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0094(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         7763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1646
_refine_ls_R_factor_gt           0.0852
_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/[\s^2^(Fo^2^)+(0.0932P)^2^+2.0768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2314
_reflns_number_gt                3928
_reflns_number_total             7763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ao5027sup1.cif
_cod_data_source_block           IV
_cod_depositor_comments
;

2022-12-20
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C20 H19 F N8 O2), C3 H7 N O'
_cod_original_formula_sum        'C43 H45 F2 N17 O5'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     917.94
_cod_database_code               2311714