# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NIRTOSH2O
_database_code_depnum_ccdc_archive 'CCDC 2259631'
loop_
_audit_author_name
_audit_author_address
'Ramesh Devarapalli'
;Cipla Limited
India
;
_audit_update_record             
;
2023-04-28 deposited with the CCDC.	2024-03-13 downloaded from the CCDC.
;
_audit_creation_date             2023-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        'Niraparib tosylate monohydrate'
_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_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     @100K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.1123(2)
_cell_length_b                   12.6881(3)
_cell_length_c                   13.3199(3)
_cell_angle_alpha                88.7065(17)
_cell_angle_beta                 87.275(2)
_cell_angle_gamma                82.989(2)
_cell_volume                     1191.51(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13304
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      68.1060
_cell_measurement_theta_min      3.3090
_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_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  27.00   0.50    2.00    --  -41.33  31.00 129.00  126
  2  ω    -47.00 -15.00   0.50    5.00    --  -82.50  42.00   0.00   64
  3  ω    -47.00 -15.00   0.50    5.00    --  -82.50  42.00 -30.00   64
  4  ω    -47.00 -15.00   0.50    5.00    --  -82.50  42.00 -90.00   64
  5  ω    -47.00 -15.00   0.50    5.00    --  -82.50  42.00-120.00   64
  6  ω    -24.00  35.00   0.50    2.00    --  -41.33  11.00 -60.00  118
  7  ω     18.00  80.00   0.50    2.00    --   41.33-104.00-180.00  124
  8  ω     29.00  83.00   0.50    5.00    --   96.67 -68.00-150.00  108
  9  ω     29.00  83.00   0.50    5.00    --   96.67 -68.00-180.00  108
 10  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00-120.00   54
 11  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00-150.00   54
 12  ω     28.00 105.00   0.50    5.00    --   96.67 -77.00-120.00  154
 13  ω     41.00 100.00   0.50    2.00    --   41.33-138.00 -30.00  118
 14  ω     44.00 127.00   0.50    5.00    --   96.67-145.00 -90.00  166
 15  ω     44.00 127.00   0.50    5.00    --   96.67-145.00 -30.00  166
 16  ω     44.00 127.00   0.50    5.00    --   96.67-145.00 150.00  166
 17  ω     30.00 109.00   0.50    5.00    --   96.67-117.00 120.00  158
 18  ω     30.00 109.00   0.50    5.00    --   96.67-117.00 -30.00  158
 19  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00  90.00   54
 20  ω     29.00  83.00   0.50    5.00    --   96.67 -68.00  60.00  108
 21  ω     29.00  83.00   0.50    5.00    --   96.67 -68.00 120.00  108
 22  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00 120.00   54
 23  ω     29.00  68.00   0.50    5.00    --   96.67 -59.00  90.00   78
 24  ω     27.00 127.00   0.50    5.00    --   96.67 -87.00  60.00  200
 25  ω     84.00 165.00   0.50    5.00    --   96.67  31.00 129.00  162
 26  ω     99.00 164.00   0.50    5.00    --   96.67 117.00  90.00  130
 27  ω     99.00 164.00   0.50    5.00    --   96.67 117.00 120.00  130
 28  ω     82.00 167.00   0.50    5.00    --   96.67  25.00  60.00  170
 29  ω     99.00 164.00   0.50    5.00    --   96.67 117.00 -60.00  130
 30  ω    105.00 170.00   0.50    5.00    --   96.67  96.00 -90.00  130
 31  ω     83.00 164.00   0.50    5.00    --   96.67  33.00-180.00  162
 32  ω     82.00 167.00   0.50    5.00    --   96.67  25.00 -90.00  170
 33  ω     81.00 164.00   0.50    5.00    --   96.67 145.00-180.00  166
 34  ω     78.00 163.00   0.50    5.00    --   96.67  50.00-150.00  170
 35  ω     30.00 109.00   0.50    5.00    --   96.67-117.00  30.00  158
 36  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00 -60.00   54
 37  ω     29.00  83.00   0.50    5.00    --   96.67 -68.00 -60.00  108
 38  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00   0.00   54
 39  ω     29.00  83.00   0.50    5.00    --   96.67 -68.00   0.00  108
 40  ω     29.00 110.00   0.50    2.00    --   41.33  31.00 129.00  162
 41  ω     28.00 109.00   0.50    2.00    --   41.33  32.00 150.00  162
 42  ω    -26.00  37.00   0.50    2.00    --   41.33 -32.00 150.00  126
 43  ω    -27.00  36.00   0.50    2.00    --   41.33 -31.00 -29.00  126
 44  ω    -34.00  24.00   0.50    2.00    --   41.33 -11.00-180.00  116
 45  ω    -96.00 -19.00   0.50    2.00    --  -41.33 138.00 -90.00  154
 46  ω    -57.00 -16.00   0.50    5.00    --  -82.50  50.00  60.00   82
 47  ω    -47.00 -15.00   0.50    5.00    --  -82.50  42.00 120.00   64
 48  ω    -79.00   4.00   0.50    2.00    --  -41.33 104.00  90.00  166
 49  ω   -109.00 -28.00   0.50    2.00    --  -41.33 -31.00 -29.00  162
 50  ω   -113.00 -23.00   0.50    2.00    --  -41.33 -21.00-120.00  180
 51  ω   -110.00 -14.00   0.50    2.00    --  -41.33 -77.00   0.00  192
 52  ω   -109.00 -18.00   0.50    2.00    --  -41.33 -65.00 150.00  182
 53  ω   -110.00 -14.00   0.50    2.00    --  -41.33 -77.00  90.00  192
 54  ω   -110.00 -22.00   0.50    2.00    --  -41.33 -77.00 -60.00  176
 55  ω   -110.00 -14.00   0.50    2.00    --  -41.33 -77.00-120.00  192
 56  ω   -151.00 -69.00   0.50    5.00    --  -82.50 -31.00 -29.00  164
 57  ω   -151.00 -59.00   0.50    5.00    --  -82.50-145.00 120.00  184
 58  ω   -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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3768
_reflns_number_total             4026
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_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)'
_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+0.001xFc²λ³/sin(2θ)]^-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_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0921
_refine_ls_restrained_S_all      1.109
_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/[σ²(Fo²)+(0.0000P)²+10.0451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1954
_refine_ls_wR_factor_ref         0.1971
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 1.06347(18) 0.73387(10) 0.96675(9) 0.0192(3) Uani 1 d . . .
O2 O 1.2498(5) 0.7652(3) 0.9781(3) 0.0276(9) Uani 1 d . . .
O3 O 1.0557(5) 0.6575(3) 0.8867(3) 0.0223(8) Uani 1 d . . .
O4 O 0.9770(5) 0.6963(3) 1.0614(3) 0.0237(8) Uani 1 d . . .
C20 C 0.9142(7) 0.8480(4) 0.9294(4) 0.0184(10) Uani 1 d . . .
C21 C 0.7190(8) 0.8465(4) 0.9324(4) 0.0254(12) Uani 1 d . . .
H21 H 0.6668 0.7855 0.9585 0.030 Uiso 1 calc . . R
C22 C 0.6003(9) 0.9321(5) 0.8980(4) 0.0316(14) Uani 1 d . . .
H22 H 0.4673 0.9295 0.9007 0.038 Uiso 1 calc . . R
C23 C 0.6722(10) 1.0222(5) 0.8594(4) 0.0343(15) Uani 1 d . . .
C24 C 0.8674(9) 1.0239(4) 0.8582(4) 0.0284(13) Uani 1 d . . .
H24 H 0.9192 1.0852 0.8327 0.034 Uiso 1 calc . . R
C25 C 0.9895(9) 0.9376(4) 0.8936(4) 0.0249(12) Uani 1 d . . .
H25 H 1.1223 0.9407 0.8930 0.030 Uiso 1 calc . . R
C26 C 0.5461(12) 1.1158(6) 0.8199(6) 0.057(2) Uani 1 d . . .
H26A H 0.6237 1.1706 0.7954 0.086 Uiso 1 calc . . GR
H26B H 0.4574 1.1446 0.8738 0.086 Uiso 1 calc . . GR
H26C H 0.4749 1.0935 0.7645 0.086 Uiso 1 calc . . GR
O1 O 0.0320(7) 1.4159(3) 0.6662(3) 0.0400(12) Uani 1 d . . .
N1 N 0.1063(7) 1.2499(4) 0.7270(4) 0.0232(10) Uani 1 d . . .
H1A H 0.136(15) 1.270(9) 0.783(8) 0.10(4) Uiso 1 d . . .
H1B H 0.135(10) 1.186(6) 0.717(5) 0.04(2) Uiso 1 d . . .
N2 N 0.2107(6) 1.0884(3) 0.5893(3) 0.0171(9) Uani 1 d . . .
N3 N 0.2555(6) 1.0026(3) 0.5275(3) 0.0163(9) Uani 1 d . . .
C1 C 0.0720(7) 1.3196(4) 0.6518(4) 0.0211(11) Uani 1 d . . .
C2 C 0.0845(7) 1.2761(4) 0.5485(4) 0.0216(11) Uani 1 d . . .
C3 C 0.1480(7) 1.1686(4) 0.5253(4) 0.0165(10) Uani 1 d . . .
C4 C 0.1553(8) 1.1331(4) 0.4238(4) 0.0217(11) Uani 1 d . . .
C5 C 0.0953(9) 1.2037(5) 0.3450(4) 0.0317(14) Uani 1 d . . .
H5 H 0.0996 1.1807 0.2775 0.038 Uiso 1 calc . . R
C6 C 0.0303(9) 1.3072(5) 0.3695(4) 0.0320(14) Uani 1 d . . .
H6 H -0.0129 1.3561 0.3182 0.038 Uiso 1 calc . . R
C7 C 0.0270(7) 1.3409(4) 0.4684(4) 0.0224(11) Uani 1 d . . .
H7 H -0.0177 1.4131 0.4815 0.027 Uiso 1 calc . . R
C8 C 0.2214(8) 1.0251(4) 0.4306(4) 0.0227(11) Uani 1 d . . .
H8 H 0.2390 0.9766 0.3767 0.027 Uiso 1 calc . . R
C9 C 0.3211(7) 0.9017(4) 0.5720(4) 0.0174(10) Uani 1 d . . .
C10 C 0.3231(9) 0.8892(4) 0.6741(4) 0.0282(13) Uani 1 d . . .
H10 H 0.2826 0.9482 0.7158 0.034 Uiso 1 calc . . R
C11 C 0.3835(11) 0.7915(5) 0.7173(4) 0.0415(18) Uani 1 d . . .
H11 H 0.3806 0.7837 0.7884 0.050 Uiso 1 calc . . R
C12 C 0.4487(12) 0.7044(5) 0.6576(5) 0.047(2) Uani 1 d . . .
C13 C 0.4476(8) 0.7184(4) 0.5551(4) 0.0282(13) Uani 1 d . . .
H13 H 0.4909 0.6599 0.5133 0.034 Uiso 1 calc . . R
C14 C 0.3851(7) 0.8154(4) 0.5108(4) 0.0213(11) Uani 1 d . . .
H14 H 0.3857 0.8232 0.4397 0.026 Uiso 1 calc C . R
C17 C 0.6504(12) 0.4083(5) 0.8115(5) 0.0453(19) Uani 1 d . . .
H17A H 0.5555 0.4051 0.8680 0.054 Uiso 0.50 calc A 1 R
H17B H 0.7456 0.3449 0.8176 0.054 Uiso 0.50 calc A 1 R
H17C H 0.6336 0.3439 0.8528 0.054 Uiso 0.50 calc A 2 R
H17D H 0.7879 0.4078 0.7956 0.054 Uiso 0.50 calc A 2 R
C18 C 0.5515(9) 0.4015(4) 0.7141(4) 0.0303(13) Uani 1 d C . .
H18A H 0.4649 0.3460 0.7208 0.036 Uiso 0.50 calc B 1 R
H18B H 0.6469 0.3810 0.6592 0.036 Uiso 0.50 calc B 1 R
H18C H 0.6219 0.3439 0.6734 0.036 Uiso 0.50 calc B 2 R
H18D H 0.4227 0.3819 0.7298 0.036 Uiso 0.50 calc B 2 R
N4B N 0.7412(12) 0.4984(7) 0.8224(6) 0.0208(18) Uani 0.50 d C 1 .
H4BA H 0.8518 0.4904 0.7832 0.025 Uiso 0.50 calc C 1 R
H4BB H 0.7746 0.5002 0.8882 0.025 Uiso 0.50 calc C 1 R
C15B C 0.5680(17) 0.6002(7) 0.6889(8) 0.015(2) Uani 0.50 d C 1 .
H15B H 0.6783 0.5833 0.6401 0.018 Uiso 0.50 calc C 1 R
C16B C 0.637(2) 0.6027(14) 0.7971(13) 0.016(3) Uani 0.50 d C 1 .
H16A H 0.7206 0.6590 0.8020 0.019 Uiso 0.50 calc C 1 R
H16B H 0.5267 0.6186 0.8450 0.019 Uiso 0.50 calc C 1 R
C19A C 0.4316(16) 0.5146(8) 0.6859(9) 0.018(2) Uani 0.50 d C 1 .
H19A H 0.3814 0.5123 0.6180 0.022 Uiso 0.50 calc C 1 R
H19B H 0.3234 0.5308 0.7349 0.022 Uiso 0.50 calc C 1 R
N4A N 0.5894(12) 0.4944(6) 0.8670(6) 0.0183(18) Uani 0.50 d C 2 .
H4AA H 0.6759 0.4995 0.9153 0.022 Uiso 0.50 calc C 2 R
H4AB H 0.4768 0.4829 0.8998 0.022 Uiso 0.50 calc C 2 R
C15A C 0.449(2) 0.5907(9) 0.7180(9) 0.025(2) Uani 0.50 d C 2 .
H15A H 0.3160 0.5796 0.7382 0.030 Uiso 0.50 calc C 2 R
C16A C 0.559(2) 0.6002(14) 0.8118(14) 0.021(4) Uani 0.50 d C 2 .
H16C H 0.6830 0.6244 0.7929 0.025 Uiso 0.50 calc C 2 R
H16D H 0.4874 0.6537 0.8566 0.025 Uiso 0.50 calc C 2 R
C19B C 0.535(2) 0.5013(8) 0.6529(8) 0.022(2) Uani 0.50 d C 2 .
H19C H 0.4544 0.4947 0.5954 0.026 Uiso 0.50 calc C 2 R
H19D H 0.6622 0.5153 0.6261 0.026 Uiso 0.50 calc C 2 R
O5 O 0.2319(5) 0.4681(3) 0.9607(3) 0.0219(8) Uani 1 d . . .
H5A H 0.3272 0.4920 0.9838 0.033 Uiso 1 d . . G
H5B H 0.1612 0.5185 0.9335 0.033 Uiso 1 d . . G


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.445(4) . ?
S1 O3 1.465(4) . ?
S1 O4 1.471(4) . ?
S1 C20 1.764(5) . ?
C20 C21 1.390(8) . ?
C20 C25 1.381(7) . ?
C21 C22 1.376(8) . ?
C22 C23 1.386(9) . ?
C23 C24 1.390(9) . ?
C23 C26 1.500(8) . ?
C24 C25 1.399(8) . ?
O1 C1 1.238(6) . ?
N1 C1 1.333(7) . ?
N2 N3 1.376(6) . ?
N2 C3 1.359(6) . ?
N3 C8 1.343(6) . ?
N3 C9 1.433(6) . ?
C1 C2 1.488(7) . ?
C2 C3 1.419(7) . ?
C2 C7 1.379(7) . ?
C3 C4 1.432(7) . ?
C4 C5 1.411(7) . ?
C4 C8 1.396(7) . ?
C5 C6 1.379(8) . ?
C6 C7 1.392(8) . ?
C9 C10 1.366(7) . ?
C9 C14 1.397(7) . ?
C10 C11 1.383(8) . ?
C11 C12 1.397(8) . ?
C12 C13 1.373(9) . ?
C12 C15B 1.542(11) . ?
C12 C15A 1.635(13) . ?
C13 C14 1.385(7) . ?
C17 C18 1.515(8) . ?
C17 N4B 1.394(11) . ?
C17 N4A 1.348(11) . ?
C18 C19A 1.624(11) . ?
C18 C19B 1.486(11) . ?
N4B C16B 1.476(19) . ?
C15B C16B 1.55(2) . ?
C15B C19A 1.544(15) . ?
N4A C16A 1.513(19) . ?
C15A C16A 1.52(2) . ?
C15A C19B 1.495(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 114.0(2) . . ?
O2 S1 O4 113.2(2) . . ?
O2 S1 C20 107.4(2) . . ?
O3 S1 O4 110.6(2) . . ?
O3 S1 C20 105.0(2) . . ?
O4 S1 C20 106.0(2) . . ?
C21 C20 S1 119.7(4) . . ?
C25 C20 S1 120.8(4) . . ?
C25 C20 C21 119.4(5) . . ?
C22 C21 C20 120.9(5) . . ?
C21 C22 C23 121.0(6) . . ?
C22 C23 C24 117.9(5) . . ?
C22 C23 C26 122.0(7) . . ?
C24 C23 C26 120.1(6) . . ?
C23 C24 C25 121.7(5) . . ?
C20 C25 C24 119.1(5) . . ?
C3 N2 N3 103.7(4) . . ?
N2 N3 C9 118.6(4) . . ?
C8 N3 N2 113.3(4) . . ?
C8 N3 C9 128.0(4) . . ?
O1 C1 N1 122.2(5) . . ?
O1 C1 C2 121.1(5) . . ?
N1 C1 C2 116.7(5) . . ?
C3 C2 C1 124.2(5) . . ?
C7 C2 C1 119.9(5) . . ?
C7 C2 C3 115.8(5) . . ?
N2 C3 C2 128.0(5) . . ?
N2 C3 C4 111.3(4) . . ?
C2 C3 C4 120.7(4) . . ?
C5 C4 C3 120.7(5) . . ?
C8 C4 C3 104.3(4) . . ?
C8 C4 C5 135.0(5) . . ?
C6 C5 C4 117.7(5) . . ?
C5 C6 C7 120.9(5) . . ?
C2 C7 C6 124.2(5) . . ?
N3 C8 C4 107.3(4) . . ?
C10 C9 N3 120.4(4) . . ?
C10 C9 C14 119.5(5) . . ?
C14 C9 N3 120.0(4) . . ?
C9 C10 C11 120.6(5) . . ?
C10 C11 C12 120.7(5) . . ?
C11 C12 C15B 128.0(6) . . ?
C11 C12 C15A 113.1(7) . . ?
C13 C12 C11 117.9(5) . . ?
C13 C12 C15B 112.3(6) . . ?
C13 C12 C15A 125.6(6) . . ?
C15B C12 C15A 33.9(5) . . ?
C12 C13 C14 121.9(5) . . ?
C13 C14 C9 119.2(5) . . ?
N4B C17 C18 116.0(6) . . ?
N4A C17 C18 115.2(6) . . ?
N4A C17 N4B 52.5(6) . . ?
C17 C18 C19A 110.8(6) . . ?
C19B C18 C17 114.1(6) . . ?
C19B C18 C19A 31.0(5) . . ?
C17 N4B C16B 118.0(9) . . ?
C12 C15B C16B 112.8(9) . . ?
C12 C15B C19A 104.9(8) . . ?
C19A C15B C16B 108.0(10) . . ?
N4B C16B C15B 109.1(11) . . ?
C15B C19A C18 107.3(8) . . ?
C17 N4A C16A 117.1(9) . . ?
C16A C15A C12 106.2(10) . . ?
C19B C15A C12 110.7(9) . . ?
C19B C15A C16A 112.7(11) . . ?
N4A C16A C15A 110.6(12) . . ?
C18 C19B C15A 108.7(9) . . ?

_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
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NIRTOSPRO
_database_code_depnum_ccdc_archive 'CCDC 2259632'
loop_
_audit_author_name
_audit_author_address
'Ramesh Devarapalli'
;Cipla Limited
India
;
_audit_update_record             
;
2023-04-28 deposited with the CCDC.	2024-03-13 downloaded from the CCDC.
;
_audit_creation_date             2023-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        'Niraparib tosylate L-proline'
_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_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     @100K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.92870(10)
_cell_length_b                   22.8760(4)
_cell_length_c                   10.8603(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.155(2)
_cell_angle_gamma                90.00
_cell_volume                     1461.46(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8405
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.1110
_cell_measurement_theta_min      3.8340
_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_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_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_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00 110.00   0.50    1.00    --   41.33  63.00 -13.00  182
  2  ω     74.00 164.00   0.50    5.00    --   96.67  63.00 -13.00  180
  3  ω    105.00 170.00   0.50    5.00    --   96.67  96.00  90.00  130
  4  ω    105.00 170.00   0.50    5.00    --   96.67  96.00  30.00  130
  5  ω     99.00 164.00   0.50    5.00    --   96.67 117.00  60.00  130
  6  ω     80.00 163.00   0.50    5.00    --   96.67  42.00 -60.00  166
  7  ω    105.00 170.00   0.50    5.00    --   96.67  96.00-120.00  130
  8  ω     99.00 164.00   0.50    5.00    --   96.67 117.00-150.00  130
  9  ω     82.00 167.00   0.50    5.00    --   96.67  25.00  60.00  170
 10  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00 -30.00   54
 11  ω     29.00  83.00   0.50    5.00    --   96.67 -68.00 -60.00  108
 12  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00-120.00   54
 13  ω     28.00  74.00   0.50    5.00    --   96.67 -63.00-150.00   92
 14  ω     29.00  83.00   0.50    5.00    --   96.67 -68.00-180.00  108
 15  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00   0.00   54
 16  ω     29.00  68.00   0.50    5.00    --   96.67 -59.00  60.00   78
 17  ω     29.00  68.00   0.50    5.00    --   96.67 -59.00 120.00   78
 18  ω     30.00  57.00   0.50    5.00    --   96.67 -50.00 120.00   54
 19  ω     22.00 106.00   0.50    5.00    --   96.67 -96.00 150.00  168
 20  ω     18.00  80.00   0.50    1.00    --   41.33-104.00  30.00  124
 21  ω    -26.00  64.00   0.50    1.00    --   41.33 -63.00-150.00  180
 22  ω    -34.00  24.00   0.50    1.00    --   41.33 -11.00-180.00  116
 23  ω    -37.00  27.00   0.50    1.00    --  -41.33  32.00-180.00  128
 24  ω    -64.00  27.00   0.50    1.00    --  -41.33  63.00 -13.00  182
 25  ω    -37.00  27.00   0.50    1.00    --  -41.33  32.00 120.00  128
 26  ω    -47.00 -15.00   0.50    5.00    --  -82.50  42.00  60.00   64
 27  ω    -47.00 -15.00   0.50    5.00    --  -82.50  42.00   0.00   64
 28  ω    -47.00 -15.00   0.50    5.00    --  -82.50  42.00  90.00   64
 29  ω    -74.00 -14.00   0.50    5.00    --  -82.50  63.00 -13.00  120
 30  ω   -101.00 -23.00   0.50    5.00    --  -82.50 145.00  60.00  156
 31  ω    -34.00  24.00   0.50    1.00    --   41.33 -11.00 150.00  116
 32  ω     18.00 109.00   0.50    1.00    --   41.33  65.00  60.00  182
 33  ω     18.00 109.00   0.50    1.00    --   41.33  65.00 120.00  182
 34  ω   -110.00 -18.00   0.50    1.00    --  -41.33 -63.00-150.00  184
 35  ω   -108.00 -24.00   0.50    1.00    --  -41.33 -43.00-120.00  168
 36  ω   -109.00 -18.00   0.50    1.00    --  -41.33 -65.00-120.00  182
 37  ω   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00   0.00  192
 38  ω   -109.00 -18.00   0.50    1.00    --  -41.33 -65.00 150.00  182
 39  ω   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00 120.00  192
 40  ω   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00 -60.00  192
 41  ω   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00-180.00  192
 42  ω   -110.00 -14.00   0.50    1.00    --  -41.33 -77.00  60.00  192
 43  ω   -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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4256
_reflns_number_total             4515
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_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)'
_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_coef       ?
_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_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.050
_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/[σ²(Fo²)+(0.0609P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.6030(3) 0.25339(9) 0.91846(18) 0.0380(5) Uani 1 d . . .
N1 N -0.2761(4) 0.30167(11) 0.9770(2) 0.0326(5) Uani 1 d . . .
H1A H -0.252(5) 0.2832(15) 1.043(3) 0.034(8) Uiso 1 d . . .
H1B H -0.186(7) 0.3287(19) 0.960(4) 0.062(12) Uiso 1 d . . .
C1 C -0.4648(4) 0.29177(12) 0.8986(2) 0.0278(5) Uani 1 d . . .
N2 N -0.1533(3) 0.39078(9) 0.81754(18) 0.0223(4) Uani 1 d . . .
C2 C -0.5039(4) 0.32826(11) 0.7858(2) 0.0246(5) Uani 1 d . . .
N3 N -0.0861(3) 0.43505(9) 0.74676(18) 0.0220(4) Uani 1 d . . .
C3 C -0.3528(4) 0.37305(11) 0.7531(2) 0.0220(5) Uani 1 d . . .
N4 N 0.8092(3) 0.67381(9) 0.95178(18) 0.0239(4) Uani 1 d . . .
H4A H 0.7505 0.7098 0.9682 0.029 Uiso 1 calc . . R
H4B H 0.8771 0.6770 0.8804 0.029 Uiso 1 calc . . R
C4 C -0.4079(4) 0.40576(11) 0.6434(2) 0.0241(5) Uani 1 d . . .
C5 C -0.6120(4) 0.39554(12) 0.5629(2) 0.0278(5) Uani 1 d . . .
H5 H -0.6488 0.4178 0.4892 0.033 Uiso 1 calc . . R
C6 C -0.7531(4) 0.35271(12) 0.5954(2) 0.0291(6) Uani 1 d . . .
H6 H -0.8907 0.3449 0.5433 0.035 Uiso 1 calc . . R
C7 C -0.6985(4) 0.31971(12) 0.7050(2) 0.0275(5) Uani 1 d . . .
H7 H -0.8014 0.2901 0.7237 0.033 Uiso 1 calc . . R
C8 C -0.2300(4) 0.44597(11) 0.6436(2) 0.0247(5) Uani 1 d . . .
H8 H -0.2141 0.4751 0.5830 0.030 Uiso 1 calc . . R
C9 C 0.1203(4) 0.46579(11) 0.7865(2) 0.0224(5) Uani 1 d . . .
C10 C 0.2446(4) 0.45277(11) 0.8999(2) 0.0227(5) Uani 1 d . . .
H10 H 0.1973 0.4220 0.9495 0.027 Uiso 1 calc . . R
C11 C 0.4393(4) 0.48500(11) 0.9410(2) 0.0225(5) Uani 1 d . . .
H11 H 0.5227 0.4764 1.0194 0.027 Uiso 1 calc . . R
C12 C 0.5121(4) 0.52942(10) 0.8685(2) 0.0209(5) Uani 1 d . . .
C13 C 0.3891(4) 0.53962(11) 0.7523(2) 0.0245(5) Uani 1 d . . .
H13 H 0.4415 0.5686 0.7001 0.029 Uiso 1 calc . . R
C14 C 0.1940(4) 0.50892(11) 0.7107(2) 0.0252(5) Uani 1 d . . .
H14 H 0.1116 0.5171 0.6319 0.030 Uiso 1 calc . . R
C15 C 0.7115(4) 0.56954(11) 0.9083(2) 0.0216(5) Uani 1 d . . .
H15 H 0.8027 0.5727 0.8371 0.026 Uiso 1 calc . . R
C16 C 0.6209(4) 0.63044(11) 0.9319(2) 0.0245(5) Uani 1 d . . .
H16A H 0.5116 0.6426 0.8600 0.029 Uiso 1 calc . . R
H16B H 0.5392 0.6294 1.0060 0.029 Uiso 1 calc . . R
C17 C 0.9841(4) 0.65671(12) 1.0569(2) 0.0279(5) Uani 1 d . . .
H17A H 0.9172 0.6591 1.1359 0.033 Uiso 1 calc . . R
H17B H 1.1134 0.6844 1.0618 0.033 Uiso 1 calc . . R
C18 C 1.0695(4) 0.59502(11) 1.0398(2) 0.0267(5) Uani 1 d . . .
H18A H 1.1766 0.5839 1.1134 0.032 Uiso 1 calc . . R
H18B H 1.1531 0.5939 0.9664 0.032 Uiso 1 calc . . R
C19 C 0.8737(4) 0.55102(11) 1.0223(2) 0.0242(5) Uani 1 d . . .
H19A H 0.7927 0.5506 1.0967 0.029 Uiso 1 calc . . R
H19B H 0.9331 0.5113 1.0101 0.029 Uiso 1 calc . . R
S1 S 1.60884(9) 0.56145(3) 0.37686(5) 0.02521(14) Uani 1 d . . .
O2 O 1.5662(3) 0.60301(9) 0.27851(17) 0.0360(4) Uani 1 d . . .
O3 O 1.8474(3) 0.55400(9) 0.42422(19) 0.0412(5) Uani 1 d . . .
O4 O 1.4728(3) 0.57143(9) 0.47757(17) 0.0396(5) Uani 1 d . . .
C20 C 1.5166(4) 0.49206(12) 0.3151(2) 0.0246(5) Uani 1 d . . .
C21 C 1.6683(4) 0.44635(12) 0.3130(2) 0.0270(5) Uani 1 d . . .
H21 H 1.8243 0.4521 0.3427 0.032 Uiso 1 calc . . R
C22 C 1.5934(4) 0.39214(12) 0.2676(2) 0.0287(6) Uani 1 d . . .
H22 H 1.6992 0.3610 0.2668 0.034 Uiso 1 calc . . R
C23 C 1.3652(4) 0.38254(12) 0.2230(2) 0.0277(5) Uani 1 d . . .
C24 C 1.2157(4) 0.42961(12) 0.2252(2) 0.0260(5) Uani 1 d . . .
H24 H 1.0602 0.4243 0.1939 0.031 Uiso 1 calc . . R
C25 C 1.2876(4) 0.48378(12) 0.2716(2) 0.0248(5) Uani 1 d . . .
H25 H 1.1821 0.5149 0.2738 0.030 Uiso 1 calc . . R
C26 C 1.2798(5) 0.32365(13) 0.1772(3) 0.0357(6) Uani 1 d . . .
H26A H 1.2327 0.3255 0.0876 0.054 Uiso 1 calc . . GR
H26B H 1.1498 0.3124 0.2195 0.054 Uiso 1 calc . . GR
H26C H 1.4013 0.2947 0.1947 0.054 Uiso 1 calc . . GR
O5 O 0.9574(3) 0.67263(9) 0.71930(17) 0.0355(4) Uani 1 d . . .
N5 N 1.1419(4) 0.64810(10) 0.51629(18) 0.0290(5) Uani 1 d . . .
H5A H 1.2374 0.6178 0.5024 0.035 Uiso 1 calc . . R
H5B H 1.0191 0.6331 0.5497 0.035 Uiso 1 calc . . R
O6 O 1.2283(3) 0.73543(10) 0.79651(19) 0.0418(5) Uani 1 d . . .
C27 C 1.1386(4) 0.70106(12) 0.7170(2) 0.0292(6) Uani 1 d . . .
C28 C 1.2648(4) 0.69158(11) 0.6038(2) 0.0260(5) Uani 1 d . . .
H28 H 1.4211 0.6766 0.6323 0.031 Uiso 1 calc . . R
C29 C 1.2832(5) 0.74633(13) 0.5248(3) 0.0391(7) Uani 1 d . . .
H29A H 1.1681 0.7757 0.5416 0.047 Uiso 1 calc . . R
H29B H 1.4361 0.7640 0.5425 0.047 Uiso 1 calc . . R
C30 C 1.2407(5) 0.72542(14) 0.3914(3) 0.0362(6) Uani 1 d . . .
H30A H 1.1821 0.7574 0.3349 0.043 Uiso 1 calc . . R
H30B H 1.3809 0.7093 0.3636 0.043 Uiso 1 calc . . R
C31 C 1.0647(6) 0.67862(16) 0.3981(3) 0.0517(9) Uani 1 d . . .
H31A H 0.9119 0.6959 0.3995 0.062 Uiso 1 calc . . R
H31B H 1.0602 0.6516 0.3267 0.062 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.238(3) . ?
N1 H1A 0.83(4) . ?
N1 H1B 0.85(4) . ?
N1 C1 1.338(4) . ?
C1 C2 1.477(4) . ?
N2 N3 1.361(3) . ?
N2 C3 1.359(3) . ?
C2 C3 1.434(3) . ?
C2 C7 1.374(3) . ?
N3 C8 1.344(3) . ?
N3 C9 1.431(3) . ?
C3 C4 1.411(4) . ?
N4 H4A 0.9200 . ?
N4 H4B 0.9200 . ?
N4 C16 1.489(3) . ?
N4 C17 1.496(3) . ?
C4 C5 1.421(3) . ?
C4 C8 1.399(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.363(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.413(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 C14 1.389(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C12 C13 1.396(3) . ?
C12 C15 1.516(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(3) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.526(3) . ?
C15 C19 1.530(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.519(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.530(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
S1 O2 1.429(2) . ?
S1 O3 1.4537(18) . ?
S1 O4 1.4557(19) . ?
S1 C20 1.783(3) . ?
C20 C21 1.381(4) . ?
C20 C25 1.394(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.396(3) . ?
C23 C24 1.397(4) . ?
C23 C26 1.502(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(4) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O5 C27 1.259(3) . ?
N5 H5A 0.9200 . ?
N5 H5B 0.9200 . ?
N5 C28 1.501(3) . ?
N5 C31 1.483(4) . ?
O6 C27 1.238(3) . ?
C27 C28 1.532(3) . ?
C28 H28 1.0000 . ?
C28 C29 1.530(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.516(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.503(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 121(3) . . ?
C1 N1 H1A 120(2) . . ?
C1 N1 H1B 119(3) . . ?
O1 C1 N1 121.9(3) . . ?
O1 C1 C2 120.4(2) . . ?
N1 C1 C2 117.6(2) . . ?
C3 N2 N3 103.21(18) . . ?
C3 C2 C1 124.8(2) . . ?
C7 C2 C1 118.8(2) . . ?
C7 C2 C3 116.4(2) . . ?
N2 N3 C9 119.69(18) . . ?
C8 N3 N2 114.15(18) . . ?
C8 N3 C9 126.2(2) . . ?
N2 C3 C2 128.0(2) . . ?
N2 C3 C4 111.8(2) . . ?
C4 C3 C2 120.2(2) . . ?
H4A N4 H4B 107.9 . . ?
C16 N4 H4A 109.2 . . ?
C16 N4 H4B 109.2 . . ?
C16 N4 C17 111.85(19) . . ?
C17 N4 H4A 109.2 . . ?
C17 N4 H4B 109.2 . . ?
C3 C4 C5 121.4(2) . . ?
C8 C4 C3 104.6(2) . . ?
C8 C4 C5 133.9(2) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 C4 117.5(2) . . ?
C6 C5 H5 121.2 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 123.3(2) . . ?
C2 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
N3 C8 C4 106.2(2) . . ?
N3 C8 H8 126.9 . . ?
C4 C8 H8 126.9 . . ?
C10 C9 N3 120.1(2) . . ?
C10 C9 C14 120.5(2) . . ?
C14 C9 N3 119.4(2) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 118.1(2) . . ?
C11 C12 C15 124.6(2) . . ?
C13 C12 C15 117.2(2) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 C12 122.2(2) . . ?
C14 C13 H13 118.9 . . ?
C9 C14 H14 120.6 . . ?
C13 C14 C9 118.7(2) . . ?
C13 C14 H14 120.6 . . ?
C12 C15 H15 107.5 . . ?
C12 C15 C16 108.80(18) . . ?
C12 C15 C19 116.9(2) . . ?
C16 C15 H15 107.5 . . ?
C16 C15 C19 108.38(19) . . ?
C19 C15 H15 107.5 . . ?
N4 C16 C15 111.06(18) . . ?
N4 C16 H16A 109.4 . . ?
N4 C16 H16B 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N4 C17 H17A 109.4 . . ?
N4 C17 H17B 109.4 . . ?
N4 C17 C18 111.1(2) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C17 C18 C19 111.52(19) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C15 C19 H19A 110.1 . . ?
C15 C19 H19B 110.1 . . ?
C18 C19 C15 107.99(19) . . ?
C18 C19 H19A 110.1 . . ?
C18 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
O2 S1 O3 114.59(12) . . ?
O2 S1 O4 113.23(12) . . ?
O2 S1 C20 107.09(11) . . ?
O3 S1 O4 111.00(12) . . ?
O3 S1 C20 105.55(12) . . ?
O4 S1 C20 104.46(11) . . ?
C21 C20 S1 120.72(18) . . ?
C21 C20 C25 120.0(2) . . ?
C25 C20 S1 119.3(2) . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 117.6(2) . . ?
C22 C23 C26 121.9(2) . . ?
C24 C23 C26 120.6(2) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 C23 121.9(2) . . ?
C25 C24 H24 119.0 . . ?
C20 C25 H25 120.4 . . ?
C24 C25 C20 119.2(2) . . ?
C24 C25 H25 120.4 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H5A N5 H5B 108.4 . . ?
C28 N5 H5A 110.1 . . ?
C28 N5 H5B 110.1 . . ?
C31 N5 H5A 110.1 . . ?
C31 N5 H5B 110.1 . . ?
C31 N5 C28 108.0(2) . . ?
O5 C27 C28 116.5(2) . . ?
O6 C27 O5 127.4(2) . . ?
O6 C27 C28 116.0(2) . . ?
N5 C28 C27 110.8(2) . . ?
N5 C28 H28 109.1 . . ?
N5 C28 C29 104.5(2) . . ?
C27 C28 H28 109.1 . . ?
C29 C28 C27 114.2(2) . . ?
C29 C28 H28 109.1 . . ?
C28 C29 H29A 110.7 . . ?
C28 C29 H29B 110.7 . . ?
H29A C29 H29B 108.8 . . ?
C30 C29 C28 105.2(2) . . ?
C30 C29 H29A 110.7 . . ?
C30 C29 H29B 110.7 . . ?
C29 C30 H30A 111.3 . . ?
C29 C30 H30B 111.3 . . ?
H30A C30 H30B 109.2 . . ?
C31 C30 C29 102.3(2) . . ?
C31 C30 H30A 111.3 . . ?
C31 C30 H30B 111.3 . . ?
N5 C31 C30 103.6(2) . . ?
N5 C31 H31A 111.0 . . ?
N5 C31 H31B 111.0 . . ?
C30 C31 H31A 111.0 . . ?
C30 C31 H31B 111.0 . . ?
H31A C31 H31B 109.0 . . ?

_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
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
