Salts of rucaparib with dicarboxylic acids: synthesis, crystal structures and solubility aspects
Wu, Chao; Gao, Lu; Xiong, Jing; Dai, Xia-Lin; Gao, Wei; Lu, Tongbu; Chen, Jia-Mei; CrystEngComm  (2022) –; doi:10.1039/D2CE00842D

data_7245644
_publ_section_title
;
 Salts of rucaparib with dicarboxylic acids: synthesis, crystal structures
 and solubility aspects
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00842D
_journal_year                    2022
_chemical_formula_moiety         'C19 H19 F N3 O, C2 H O2, 2.5(H2 O)'
_chemical_formula_sum            'C21 H25 F N3 O5.5'
_chemical_formula_weight         426.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-21 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.612(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7628(4)
_cell_length_b                   9.9401(2)
_cell_length_c                   14.6764(3)
_cell_measurement_reflns_used    7579
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.0700
_cell_measurement_theta_min      5.4120
_cell_volume                     2090.64(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -86.00 -26.00   0.50    0.50    --    0.00 -57.00  60.00  120
  2  \w    -85.00 -22.00   0.50    0.50    --    0.00 -37.00 -60.00  126
  3  \w    -32.00  29.00   0.50    0.50    --    0.00 -37.00 -30.00  122
  4  \w     -9.00  23.00   0.50    0.50    --    0.00 -57.00  60.00   64
  5  \w    101.00 135.00   0.50    2.50    --  106.20 -45.00 -90.00   68
  6  \w     27.00  53.00   0.50    2.50    --  106.20 -45.00  90.00   52
  7  \w     77.00 195.00   0.50    2.50    --  106.20  30.00 -90.00  236
  8  \w     17.00  90.00   0.50    2.50    --  106.20 -45.00 -90.00  146
  9  \w     78.00 103.00   0.50    2.50    --  106.20 -45.00 -30.00   50
 10  \w     21.00 136.00   0.50    2.50    --  106.20 -61.00 -90.00  230
 11  \w     73.00 103.00   0.50    2.50    --  106.20  30.00 -60.00   60
 12  \w    151.00 196.00   0.50    2.50    --  106.20  30.00 -60.00   90
 13  \w     87.00 139.00   0.50    2.50    --  106.20  45.00  30.00  104
 14  \w     18.00  43.00   0.50    2.50    --  106.20 -45.00 -30.00   50
 15  \w     58.00 128.00   0.50    2.50    --  106.20 -45.00  90.00  140
 16  \w     63.00  89.00   0.50    2.50    --  106.20 -77.00-180.00   52
 17  \w     83.00 125.00   0.50    2.50    --  106.20 -30.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0037382000
_diffrn_orient_matrix_UB_12      -0.0699897000
_diffrn_orient_matrix_UB_13      -0.0952075000
_diffrn_orient_matrix_UB_21      0.1055621000
_diffrn_orient_matrix_UB_22      0.0231875000
_diffrn_orient_matrix_UB_23      0.0352093000
_diffrn_orient_matrix_UB_31      0.0199521000
_diffrn_orient_matrix_UB_32      -0.1363559000
_diffrn_orient_matrix_UB_33      0.0549909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13232
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.394
_diffrn_reflns_theta_min         5.416
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       flake-shaped
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0959P)^2^+0.4635P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3938
_reflns_number_total             4449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00842d2.cif
_cod_data_source_block           rucaparib_fumaric_acid
_cod_original_formula_sum        'C21 H25 F N3 O5.50'
_cod_database_code               7245644
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: O4(0.5) H4A(0.5) H4B(0.5)
3.a Free rotating group:
 O4(H4A,H4B)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C6(H6), C19(H19), C17(H17), C20(H20), C7(H7)
3.d Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
;
_shelx_res_checksum              81003
_shelx_hkl_checksum              93289
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.767
_oxdiff_exptl_absorpt_empirical_full_min 0.428