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_7245646
_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, C7 H11 O4'
_chemical_formula_sum            'C26 H30 F N3 O5'
_chemical_formula_weight         483.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.4657(3)
_cell_length_b                   15.6448(2)
_cell_length_c                   5.56040(10)
_cell_measurement_reflns_used    17827
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.9970
_cell_measurement_theta_min      3.1940
_cell_volume                     2389.28(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -28.00  70.00   0.50    1.50    --    0.00  57.00  60.00  196
  2  \w     12.00  38.00   0.50    1.50    --    0.00  57.00-120.00   52
  3  \w    -88.00 -62.00   0.50    1.50    --    0.00 -37.00  90.00   52
  4  \w    -39.00  47.00   0.50    1.50    --    0.00 -19.00-120.00  172
  5  \w    -26.00  71.00   0.50    1.50    --    0.00  57.00 120.00  194
  6  \w    -43.00 -17.00   0.50    1.50    --    0.00 -37.00  90.00   52
  7  \w     62.00  88.00   0.50    2.50    --  106.20 -77.00 -30.00   52
  8  \w     91.00 117.00   0.50    2.50    --  106.20 -30.00-180.00   52
  9  \w     60.00  98.00   0.50    2.50    --  106.20 -45.00 -30.00   76
 10  \w     22.00  50.00   0.50    2.50    --  106.20 -30.00-180.00   56
 11  \w     74.00 122.00   0.50    2.50    --  106.20 -82.00  90.00   96
 12  \w    165.00 192.00   0.50    2.50    --  106.20  45.00 -90.00   54
 13  \w     57.00 143.00   0.50    2.50    --  106.20 -82.00  30.00  172
 14  \w     47.00 143.00   0.50    2.50    --  106.20 -82.00 -30.00  192
 15  \w     78.00 195.00   0.50    2.50    --  106.20  45.00 150.00  234
 16  \w     85.00 193.00   0.50    2.50    --  106.20  82.00-120.00  216
 17  \w     57.00 106.00   0.50    2.50    --  106.20 -82.00 150.00   98
 18  \w     67.00 143.00   0.50    2.50    --  106.20 -82.00-150.00  152
 19  \w    125.00 189.00   0.50    2.50    --  106.20  45.00  30.00  128
 20  \w     18.00  71.00   0.50    2.50    --  106.20 -45.00 150.00  106
 21  \w     77.00 102.00   0.50    2.50    --  106.20 -45.00 150.00   50
 22  \w     94.00 131.00   0.50    2.50    --  106.20 -82.00 -90.00   74
 23  \w     78.00 115.00   0.50    2.50    --  106.20  45.00  30.00   74
 24  \w     73.00 134.00   0.50    2.50    --  106.20 -45.00-150.00  122
 25  \w     79.00 192.00   0.50    2.50    --  106.20  30.00 -90.00  226
 26  \w    101.00 184.00   0.50    2.50    --  106.20  45.00 -30.00  166
 27  \w     27.00  52.00   0.50    2.50    --  106.20 -45.00 -30.00   50
 28  \w     45.00 127.00   0.50    2.50    --  106.20 -82.00-180.00  164
;
_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      0.0450141000
_diffrn_orient_matrix_UB_12      -0.0491420000
_diffrn_orient_matrix_UB_13      -0.0905208000
_diffrn_orient_matrix_UB_21      -0.0271477000
_diffrn_orient_matrix_UB_22      -0.0220760000
_diffrn_orient_matrix_UB_23      -0.2343102000
_diffrn_orient_matrix_UB_31      0.0195812000
_diffrn_orient_matrix_UB_32      0.0824329000
_diffrn_orient_matrix_UB_33      -0.1168132000
_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  0.0886
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            28889
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.384
_diffrn_reflns_theta_min         3.218
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       needle-shaped
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0746P)^2^+0.2256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                4838
_reflns_number_total             5102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00842d2.cif
_cod_data_source_block           rucaparib_pimelic_acid
_cod_database_code               7245646
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.93
_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
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C24(H24A,H24B), C14(H14A,H14B), C13(H13A,H13B), C25(H25A,H25B),
 C23(H23A,H23B), C22(H22A,H22B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C4(H4), C7(H7), C19(H19), C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
;
_shelx_res_checksum              35614
_shelx_hkl_checksum              77846
_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 3.541
_oxdiff_exptl_absorpt_empirical_full_min 0.391