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_7248310
_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         'C7 H7 O3 S, C19 H21 N4 O, H2 O'
_chemical_formula_sum            'C26 H30 N4 O5 S'
_chemical_formula_weight         510.60
_chemical_name_systematic        'Niraparib tosylate monohydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                88.7065(17)
_cell_angle_beta                 87.275(2)
_cell_angle_gamma                82.989(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1123(2)
_cell_length_b                   12.6881(3)
_cell_length_c                   13.3199(3)
_cell_measurement_reflns_used    13304
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      68.1060
_cell_measurement_theta_min      3.3090
_cell_volume                     1191.50(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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9890
_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    -36.00  27.00   0.50    2.00    --  -41.33  31.00 129.00  126
  2  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00   0.00   64
  3  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00 -30.00   64
  4  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00 -90.00   64
  5  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00-120.00   64
  6  \w    -24.00  35.00   0.50    2.00    --  -41.33  11.00 -60.00  118
  7  \w     18.00  80.00   0.50    2.00    --   41.33-104.00-180.00  124
  8  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00-150.00  108
  9  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00-180.00  108
 10  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00-120.00   54
 11  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00-150.00   54
 12  \w     28.00 105.00   0.50    5.00    --   96.67 -77.00-120.00  154
 13  \w     41.00 100.00   0.50    2.00    --   41.33-138.00 -30.00  118
 14  \w     44.00 127.00   0.50    5.00    --   96.67-145.00 -90.00  166
 15  \w     44.00 127.00   0.50    5.00    --   96.67-145.00 -30.00  166
 16  \w     44.00 127.00   0.50    5.00    --   96.67-145.00 150.00  166
 17  \w     30.00 109.00   0.50    5.00    --   96.67-117.00 120.00  158
 18  \w     30.00 109.00   0.50    5.00    --   96.67-117.00 -30.00  158
 19  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00  90.00   54
 20  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00  60.00  108
 21  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00 120.00  108
 22  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00 120.00   54
 23  \w     29.00  68.00   0.50    5.00    --   96.67 -59.00  90.00   78
 24  \w     27.00 127.00   0.50    5.00    --   96.67 -87.00  60.00  200
 25  \w     84.00 165.00   0.50    5.00    --   96.67  31.00 129.00  162
 26  \w     99.00 164.00   0.50    5.00    --   96.67 117.00  90.00  130
 27  \w     99.00 164.00   0.50    5.00    --   96.67 117.00 120.00  130
 28  \w     82.00 167.00   0.50    5.00    --   96.67  25.00  60.00  170
 29  \w     99.00 164.00   0.50    5.00    --   96.67 117.00 -60.00  130
 30  \w    105.00 170.00   0.50    5.00    --   96.67  96.00 -90.00  130
 31  \w     83.00 164.00   0.50    5.00    --   96.67  33.00-180.00  162
 32  \w     82.00 167.00   0.50    5.00    --   96.67  25.00 -90.00  170
 33  \w     81.00 164.00   0.50    5.00    --   96.67 145.00-180.00  166
 34  \w     78.00 163.00   0.50    5.00    --   96.67  50.00-150.00  170
 35  \w     30.00 109.00   0.50    5.00    --   96.67-117.00  30.00  158
 36  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00 -60.00   54
 37  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00 -60.00  108
 38  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00   0.00   54
 39  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00   0.00  108
 40  \w     29.00 110.00   0.50    2.00    --   41.33  31.00 129.00  162
 41  \w     28.00 109.00   0.50    2.00    --   41.33  32.00 150.00  162
 42  \w    -26.00  37.00   0.50    2.00    --   41.33 -32.00 150.00  126
 43  \w    -27.00  36.00   0.50    2.00    --   41.33 -31.00 -29.00  126
 44  \w    -34.00  24.00   0.50    2.00    --   41.33 -11.00-180.00  116
 45  \w    -96.00 -19.00   0.50    2.00    --  -41.33 138.00 -90.00  154
 46  \w    -57.00 -16.00   0.50    5.00    --  -82.50  50.00  60.00   82
 47  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00 120.00   64
 48  \w    -79.00   4.00   0.50    2.00    --  -41.33 104.00  90.00  166
 49  \w   -109.00 -28.00   0.50    2.00    --  -41.33 -31.00 -29.00  162
 50  \w   -113.00 -23.00   0.50    2.00    --  -41.33 -21.00-120.00  180
 51  \w   -110.00 -14.00   0.50    2.00    --  -41.33 -77.00   0.00  192
 52  \w   -109.00 -18.00   0.50    2.00    --  -41.33 -65.00 150.00  182
 53  \w   -110.00 -14.00   0.50    2.00    --  -41.33 -77.00  90.00  192
 54  \w   -110.00 -22.00   0.50    2.00    --  -41.33 -77.00 -60.00  176
 55  \w   -110.00 -14.00   0.50    2.00    --  -41.33 -77.00-120.00  192
 56  \w   -151.00 -69.00   0.50    5.00    --  -82.50 -31.00 -29.00  164
 57  \w   -151.00 -59.00   0.50    5.00    --  -82.50-145.00 120.00  184
 58  \w   -157.00 -83.00   0.50    5.00    --  -82.50 -96.00 -30.00  148
;
_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      -0.1418818000
_diffrn_orient_matrix_UB_12      0.0952807000
_diffrn_orient_matrix_UB_13      -0.0313249000
_diffrn_orient_matrix_UB_21      -0.1338651000
_diffrn_orient_matrix_UB_22      -0.0767538000
_diffrn_orient_matrix_UB_23      -0.0358392000
_diffrn_orient_matrix_UB_31      -0.0983573000
_diffrn_orient_matrix_UB_32      -0.0000552000
_diffrn_orient_matrix_UB_33      0.1055715000
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15381
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.79
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91935
_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    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.0017(2)
_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   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0921
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+10.0451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1954
_refine_ls_wR_factor_ref         0.1971
_reflns_number_gt                3768
_reflns_number_total             4026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ce00114a2.cif
_cod_data_source_block           NIRTOSH2O
_cod_depositor_comments
'Adding full bibliography for 7248310--7248311.cif.'
_cod_original_cell_volume        1191.51(5)
_cod_database_code               7248310
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     @100K
_reflns_odcompleteness_completeness 99.67
_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 C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H17A(0.5) H17B(0.5) H17C(0.5) H17D(0.5) H18A(0.5) H18B(0.5)
 H18C(0.5) H18D(0.5) N4B(0.5) H4BA(0.5) H4BB(0.5) C15B(0.5) H15B(0.5) C16B(0.5)
 H16A(0.5) H16B(0.5) C19A(0.5) H19A(0.5) H19B(0.5) N4A(0.5) H4AA(0.5) H4AB(0.5)
 C15A(0.5) H15A(0.5) C16A(0.5) H16C(0.5) H16D(0.5) C19B(0.5) H19C(0.5) H19D(0.5)
3.a Free rotating group:
 O5(H5A,H5B)
3.b Ternary CH refined with riding coordinates:
 C15B(H15B), C15A(H15A)
3.c Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C17(H17C,H17D), C18(H18A,H18B), C18(H18C,H18D), N4B(H4BA,
 H4BB), C16B(H16A,H16B), C19A(H19A,H19B), N4A(H4AA,H4AB), C16A(H16C,H16D),
 C19B(H19C,H19D)
3.d Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C24(H24), C25(H25), C5(H5), C6(H6), C7(H7), C8(H8),
 C10(H10), C11(H11), C13(H13), C14(H14)
3.e 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 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.779