A zwitterionic salt–cocrystal: in vitro insights from niraparib tosylate, an anti-cancer drug
Mudda, Ramesh Reddy; Devarapalli, Ramesh; Das, Arijit; Reddy Lakkireddy, Pulla; Reddy, C. Malla; Chennuru, Ramanaiah; CrystEngComm 26 (2024) 2463–2473; doi:10.1039/D4CE00114A

data_7248311
_publ_section_title
;
 A zwitterionic salt--cocrystal: in vitro insights from niraparib
 tosylate, an anti-cancer drug
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              2463
_journal_page_last               2473
_journal_paper_doi               10.1039/D4CE00114A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C19 H21 N4 O, C7 H7 O3 S, C5 H9 N O2'
_chemical_formula_sum            'C31 H37 N5 O6 S'
_chemical_formula_weight         607.72
_chemical_name_systematic        'Niraparib tosylate L-proline'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2023-04-28 deposited with the CCDC.	2024-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.155(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.92870(10)
_cell_length_b                   22.8760(4)
_cell_length_c                   10.8603(2)
_cell_measurement_reflns_used    8405
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.1110
_cell_measurement_theta_min      3.8340
_cell_volume                     1461.46(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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     19.00 110.00   0.50    1.00    --   41.33  63.00 -13.00  182
  2  \w     74.00 164.00   0.50    5.00    --   96.67  63.00 -13.00  180
  3  \w    105.00 170.00   0.50    5.00    --   96.67  96.00  90.00  130
  4  \w    105.00 170.00   0.50    5.00    --   96.67  96.00  30.00  130
  5  \w     99.00 164.00   0.50    5.00    --   96.67 117.00  60.00  130
  6  \w     80.00 163.00   0.50    5.00    --   96.67  42.00 -60.00  166
  7  \w    105.00 170.00   0.50    5.00    --   96.67  96.00-120.00  130
  8  \w     99.00 164.00   0.50    5.00    --   96.67 117.00-150.00  130
  9  \w     82.00 167.00   0.50    5.00    --   96.67  25.00  60.00  170
 10  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00 -30.00   54
 11  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00 -60.00  108
 12  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00-120.00   54
 13  \w     28.00  74.00   0.50    5.00    --   96.67 -63.00-150.00   92
 14  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00-180.00  108
 15  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00   0.00   54
 16  \w     29.00  68.00   0.50    5.00    --   96.67 -59.00  60.00   78
 17  \w     29.00  68.00   0.50    5.00    --   96.67 -59.00 120.00   78
 18  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00 120.00   54
 19  \w     22.00 106.00   0.50    5.00    --   96.67 -96.00 150.00  168
 20  \w     18.00  80.00   0.50    1.00    --   41.33-104.00  30.00  124
 21  \w    -26.00  64.00   0.50    1.00    --   41.33 -63.00-150.00  180
 22  \w    -34.00  24.00   0.50    1.00    --   41.33 -11.00-180.00  116
 23  \w    -37.00  27.00   0.50    1.00    --  -41.33  32.00-180.00  128
 24  \w    -64.00  27.00   0.50    1.00    --  -41.33  63.00 -13.00  182
 25  \w    -37.00  27.00   0.50    1.00    --  -41.33  32.00 120.00  128
 26  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00  60.00   64
 27  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00   0.00   64
 28  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00  90.00   64
 29  \w    -74.00 -14.00   0.50    5.00    --  -82.50  63.00 -13.00  120
 30  \w   -101.00 -23.00   0.50    5.00    --  -82.50 145.00  60.00  156
 31  \w    -34.00  24.00   0.50    1.00    --   41.33 -11.00 150.00  116
 32  \w     18.00 109.00   0.50    1.00    --   41.33  65.00  60.00  182
 33  \w     18.00 109.00   0.50    1.00    --   41.33  65.00 120.00  182
 34  \w   -110.00 -18.00   0.50    1.00    --  -41.33 -63.00-150.00  184
 35  \w   -108.00 -24.00   0.50    1.00    --  -41.33 -43.00-120.00  168
 36  \w   -109.00 -18.00   0.50    1.00    --  -41.33 -65.00-120.00  182
 37  \w   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00   0.00  192
 38  \w   -109.00 -18.00   0.50    1.00    --  -41.33 -65.00 150.00  182
 39  \w   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00 120.00  192
 40  \w   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00 -60.00  192
 41  \w   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00-180.00  192
 42  \w   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00  60.00  192
 43  \w   -151.00 -59.00   0.50    5.00    --  -82.50 -63.00-150.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0845097000
_diffrn_orient_matrix_UB_12      -0.0066024000
_diffrn_orient_matrix_UB_13      0.1278084000
_diffrn_orient_matrix_UB_21      0.1616529000
_diffrn_orient_matrix_UB_22      0.0493388000
_diffrn_orient_matrix_UB_23      0.0518328000
_diffrn_orient_matrix_UB_31      -0.1878609000
_diffrn_orient_matrix_UB_32      0.0453749000
_diffrn_orient_matrix_UB_33      -0.0375981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14717
_diffrn_reflns_theta_full        68.33
_diffrn_reflns_theta_max         68.33
_diffrn_reflns_theta_min         3.86
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.433
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             644
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4515
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0609P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                4256
_reflns_number_total             4515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ce00114a2.cif
_cod_data_source_block           NIRTOSPRO
_cod_depositor_comments
'Adding full bibliography for 7248310--7248311.cif.'
_cod_original_cell_volume        1461.46(4)
_cod_database_code               7248311
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     @100K
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 N5(H5A,H5B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C21(H21), C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_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 2.347
_oxdiff_exptl_absorpt_empirical_full_min 0.602