# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_rucaparib_fumaric_acid
_database_code_depnum_ccdc_archive 'CCDC 2151641'
loop_
_audit_author_name
_audit_author_address
'Chao Wu'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-08-21 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-08-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 F N3 O, C2 H O2, 2.5(H2 O)'
_chemical_formula_sum            'C21 H25 F N3 O5.50'
_chemical_formula_weight         426.44
_chemical_melting_point          ?
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'
F F 0.0727 0.0534 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.7628(4)
_cell_length_b                   9.9401(2)
_cell_length_c                   14.6764(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.612(3)
_cell_angle_gamma                90
_cell_volume                     2090.64(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7579
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.0700
_cell_measurement_theta_min      5.4120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -26.00   0.50    0.50    --    0.00 -57.00  60.00  120
  2  ω    -85.00 -22.00   0.50    0.50    --    0.00 -37.00 -60.00  126
  3  ω    -32.00  29.00   0.50    0.50    --    0.00 -37.00 -30.00  122
  4  ω     -9.00  23.00   0.50    0.50    --    0.00 -57.00  60.00   64
  5  ω    101.00 135.00   0.50    2.50    --  106.20 -45.00 -90.00   68
  6  ω     27.00  53.00   0.50    2.50    --  106.20 -45.00  90.00   52
  7  ω     77.00 195.00   0.50    2.50    --  106.20  30.00 -90.00  236
  8  ω     17.00  90.00   0.50    2.50    --  106.20 -45.00 -90.00  146
  9  ω     78.00 103.00   0.50    2.50    --  106.20 -45.00 -30.00   50
 10  ω     21.00 136.00   0.50    2.50    --  106.20 -61.00 -90.00  230
 11  ω     73.00 103.00   0.50    2.50    --  106.20  30.00 -60.00   60
 12  ω    151.00 196.00   0.50    2.50    --  106.20  30.00 -60.00   90
 13  ω     87.00 139.00   0.50    2.50    --  106.20  45.00  30.00  104
 14  ω     18.00  43.00   0.50    2.50    --  106.20 -45.00 -30.00   50
 15  ω     58.00 128.00   0.50    2.50    --  106.20 -45.00  90.00  140
 16  ω     63.00  89.00   0.50    2.50    --  106.20 -77.00-180.00   52
 17  ω     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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3938
_reflns_number_total             4449
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.091
_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/[σ²(Fo²)+(0.0959P)²+0.4635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1614
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.42718(8) 0.21982(10) 0.55702(9) 0.0489(3) Uani 1 1 d . . . . .
O2 O 0.89284(8) 1.08250(13) 0.61391(10) 0.0429(3) Uani 1 1 d . . . . .
O1 O 0.20846(8) 0.60117(13) 0.42039(10) 0.0452(3) Uani 1 1 d . . . . .
O3 O 1.04199(9) 1.13614(14) 0.65782(10) 0.0469(3) Uani 1 1 d . . . . .
N2 N 0.60771(9) 0.62343(13) 0.68664(10) 0.0328(3) Uani 1 1 d . . . . .
N3 N 0.26813(9) 0.77582(15) 0.52315(11) 0.0367(3) Uani 1 1 d . . . . .
N1 N 0.94468(10) 1.13204(14) 0.81455(12) 0.0372(3) Uani 1 1 d . . . . .
C12 C 0.48450(10) 0.76547(15) 0.62667(11) 0.0301(3) Uani 1 1 d . . . . .
C11 C 0.45107(10) 0.63056(15) 0.60082(11) 0.0299(3) Uani 1 1 d . . . . .
C8 C 0.65069(10) 0.86269(16) 0.72017(12) 0.0321(3) Uani 1 1 d . . . . .
C13 C 0.42380(11) 0.88672(15) 0.61015(12) 0.0326(3) Uani 1 1 d . . . . .
H13A H 0.411975 0.927547 0.544430 0.039 Uiso 1 1 calc R U . . .
H13B H 0.455842 0.954282 0.662924 0.039 Uiso 1 1 calc R U . . .
C10 C 0.53035(10) 0.54507(16) 0.63869(11) 0.0318(3) Uani 1 1 d . . . . .
C9 C 0.58038(10) 0.75699(16) 0.67796(11) 0.0316(3) Uani 1 1 d . . . . .
C16 C 0.36241(11) 0.57236(16) 0.54544(11) 0.0321(3) Uani 1 1 d . . . . .
C15 C 0.27531(11) 0.65115(17) 0.49406(12) 0.0351(3) Uani 1 1 d . . . . .
C5 C 0.70774(12) 1.08627(17) 0.71173(13) 0.0375(4) Uani 1 1 d . . . . .
H5 H 0.699257 1.170468 0.678444 0.045 Uiso 1 1 calc R U . . .
C4 C 0.79995(11) 0.93836(17) 0.84505(12) 0.0366(3) Uani 1 1 d . . . . .
H4 H 0.854481 0.921332 0.904396 0.044 Uiso 1 1 calc R U . . .
C18 C 0.43654(13) 0.35542(16) 0.57158(13) 0.0378(4) Uani 1 1 d . . . . .
C6 C 0.73275(11) 0.83917(16) 0.80683(12) 0.0349(3) Uani 1 1 d . . . . .
H6 H 0.742160 0.754385 0.839464 0.042 Uiso 1 1 calc R U . . .
C3 C 0.78884(11) 1.06306(16) 0.79775(12) 0.0346(3) Uani 1 1 d . . . . .
C14 C 0.33116(11) 0.84702(17) 0.61283(12) 0.0361(3) Uani 1 1 d . . . . .
H14A H 0.344080 0.789066 0.671997 0.043 Uiso 1 1 calc R U . . .
H14B H 0.299654 0.929296 0.621066 0.043 Uiso 1 1 calc R U . . .
C19 C 0.52442(12) 0.40627(16) 0.62469(12) 0.0361(3) Uani 1 1 d . . . . .
H19 H 0.578034 0.350110 0.650389 0.043 Uiso 1 1 calc R U . . .
C17 C 0.35647(12) 0.43329(17) 0.53115(12) 0.0366(3) Uani 1 1 d . . . . .
H17 H 0.297718 0.392134 0.493824 0.044 Uiso 1 1 calc R U . . .
C20 C 0.96315(12) 1.00734(16) 0.51036(13) 0.0381(4) Uani 1 1 d . . . . .
H20 H 0.905273 0.969828 0.465752 0.046 Uiso 1 1 calc R U . . .
C7 C 0.63921(11) 0.98864(17) 0.67387(12) 0.0361(3) Uani 1 1 d . . . . .
H7 H 0.583817 1.007340 0.615862 0.043 Uiso 1 1 calc R U . . .
C21 C 0.96754(11) 1.08033(17) 0.60081(13) 0.0373(4) Uani 1 1 d . . . . .
C2 C 0.86417(12) 1.16793(17) 0.83819(14) 0.0384(4) Uani 1 1 d . . . . .
H2A H 0.838836 1.256433 0.808272 0.046 Uiso 1 1 calc R U . . .
H2B H 0.885543 1.175118 0.911711 0.046 Uiso 1 1 calc R U . . .
C1 C 1.02336(15) 1.2283(2) 0.85577(17) 0.0540(5) Uani 1 1 d . . . . .
H1C H 1.002167 1.317751 0.827401 0.081 Uiso 1 1 calc R U . . .
H1D H 1.074015 1.198538 0.838346 0.081 Uiso 1 1 calc R U . . .
H1E H 1.045948 1.232155 0.928848 0.081 Uiso 1 1 calc R U . . .
O4 O 0.7731(2) 0.8599(3) 0.5260(3) 0.0657(9) Uani 0.5 1 d G . P . .
H4A H 0.810110 0.920032 0.562332 0.099 Uiso 0.5 1 d G U P . .
H4B H 0.725346 0.866047 0.538951 0.099 Uiso 0.5 1 d G U P . .
O6 O 0.78658(8) 0.50662(13) 0.74977(10) 0.0424(3) Uani 1 1 d . . . . .
O5 O 1.02820(10) 0.89513(15) 0.89761(12) 0.0527(4) Uani 1 1 d . . . . .
H3 H 0.2217(15) 0.818(2) 0.4832(15) 0.035(5) Uiso 1 1 d . . . . .
H1A H 0.9249(14) 1.127(2) 0.7463(17) 0.038(5) Uiso 1 1 d . . . . .
H6A H 0.7866(18) 0.485(2) 0.692(2) 0.057(7) Uiso 1 1 d . . . . .
H2 H 0.6659(19) 0.595(2) 0.7080(19) 0.056(6) Uiso 1 1 d . . . . .
H1B H 0.9695(18) 1.036(3) 0.8431(18) 0.060(7) Uiso 1 1 d . . . . .
H6B H 0.848(3) 0.561(3) 0.786(3) 0.095(10) Uiso 1 1 d . . . . .
H5B H 0.998(2) 0.812(3) 0.870(2) 0.075(8) Uiso 1 1 d . . . . .
H5A H 1.094(2) 0.890(3) 0.909(2) 0.087(9) Uiso 1 1 d . . . . .


_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
F1 C18 1.3631(19) . ?
O2 C21 1.2697(19) . ?
O1 C15 1.256(2) . ?
O3 C21 1.252(2) . ?
N2 C10 1.369(2) . ?
N2 C9 1.385(2) . ?
N2 H2 0.88(3) . ?
N3 C15 1.331(2) . ?
N3 C14 1.460(2) . ?
N3 H3 0.84(2) . ?
N1 C2 1.492(2) . ?
N1 C1 1.481(2) . ?
N1 H1A 0.92(2) . ?
N1 H1B 1.05(3) . ?
C12 C11 1.433(2) . ?
C12 C13 1.495(2) . ?
C12 C9 1.382(2) . ?
C11 C10 1.419(2) . ?
C11 C16 1.415(2) . ?
C8 C9 1.464(2) . ?
C8 C6 1.405(2) . ?
C8 C7 1.400(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.529(2) . ?
C10 C19 1.392(2) . ?
C16 C15 1.485(2) . ?
C16 C17 1.395(2) . ?
C5 H5 0.9500 . ?
C5 C3 1.392(2) . ?
C5 C7 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C6 1.383(2) . ?
C4 C3 1.396(2) . ?
C18 C19 1.372(2) . ?
C18 C17 1.386(2) . ?
C6 H6 0.9500 . ?
C3 C2 1.504(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C19 H19 0.9500 . ?
C17 H17 0.9500 . ?
C20 C20 1.326(3) 3_776 ?
C20 H20 0.9500 . ?
C20 C21 1.489(2) . ?
C7 H7 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
O4 H4A 0.8500 . ?
O4 H4B 0.8508 . ?
O6 H6A 0.87(3) . ?
O6 H6B 1.04(4) . ?
O5 H5B 0.96(3) . ?
O5 H5A 0.98(3) . ?

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
C10 N2 C9 108.77(13) . . ?
C10 N2 H2 125.0(16) . . ?
C9 N2 H2 125.1(16) . . ?
C15 N3 C14 128.59(15) . . ?
C15 N3 H3 114.4(14) . . ?
C14 N3 H3 117.0(14) . . ?
C2 N1 H1A 109.3(13) . . ?
C2 N1 H1B 109.7(13) . . ?
C1 N1 C2 113.53(14) . . ?
C1 N1 H1A 109.0(13) . . ?
C1 N1 H1B 108.3(15) . . ?
H1A N1 H1B 106.8(18) . . ?
C11 C12 C13 124.87(13) . . ?
C9 C12 C11 106.58(13) . . ?
C9 C12 C13 128.20(14) . . ?
C10 C11 C12 106.85(13) . . ?
C16 C11 C12 134.51(14) . . ?
C16 C11 C10 118.56(14) . . ?
C6 C8 C9 120.84(14) . . ?
C7 C8 C9 120.95(14) . . ?
C7 C8 C6 118.18(15) . . ?
C12 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
C12 C13 C14 109.97(13) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
N2 C10 C11 108.13(14) . . ?
N2 C10 C19 129.07(14) . . ?
C19 C10 C11 122.79(14) . . ?
N2 C9 C8 119.81(13) . . ?
C12 C9 N2 109.64(14) . . ?
C12 C9 C8 130.54(14) . . ?
C11 C16 C15 124.00(14) . . ?
C17 C16 C11 118.67(14) . . ?
C17 C16 C15 117.14(14) . . ?
O1 C15 N3 119.44(15) . . ?
O1 C15 C16 119.70(14) . . ?
N3 C15 C16 120.83(15) . . ?
C3 C5 H5 119.5 . . ?
C7 C5 H5 119.5 . . ?
C7 C5 C3 121.07(15) . . ?
C6 C4 H4 119.5 . . ?
C6 C4 C3 121.00(15) . . ?
C3 C4 H4 119.5 . . ?
F1 C18 C19 118.10(15) . . ?
F1 C18 C17 117.74(15) . . ?
C19 C18 C17 124.16(15) . . ?
C8 C6 H6 119.7 . . ?
C4 C6 C8 120.61(15) . . ?
C4 C6 H6 119.7 . . ?
C5 C3 C4 118.43(15) . . ?
C5 C3 C2 121.27(15) . . ?
C4 C3 C2 120.29(15) . . ?
N3 C14 C13 113.62(12) . . ?
N3 C14 H14A 108.8 . . ?
N3 C14 H14B 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C10 C19 H19 122.0 . . ?
C18 C19 C10 116.02(15) . . ?
C18 C19 H19 122.0 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.79(15) . . ?
C18 C17 H17 120.1 . . ?
C20 C20 H20 118.7 3_776 . ?
C20 C20 C21 122.6(2) 3_776 . ?
C21 C20 H20 118.7 . . ?
C8 C7 H7 119.7 . . ?
C5 C7 C8 120.70(15) . . ?
C5 C7 H7 119.7 . . ?
O2 C21 C20 116.20(15) . . ?
O3 C21 O2 124.17(16) . . ?
O3 C21 C20 119.63(15) . . ?
N1 C2 C3 110.54(12) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N1 C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H4A O4 H4B 104.5 . . ?
H6A O6 H6B 105(2) . . ?
H5B O5 H5A 109(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C18 C19 C10 -179.23(13) . . . . ?
F1 C18 C17 C16 179.01(14) . . . . ?
N2 C10 C19 C18 -178.92(15) . . . . ?
C12 C11 C10 N2 1.06(15) . . . . ?
C12 C11 C10 C19 -178.03(13) . . . . ?
C12 C11 C16 C15 2.0(2) . . . . ?
C12 C11 C16 C17 176.86(15) . . . . ?
C12 C13 C14 N3 -74.36(17) . . . . ?
C11 C12 C13 C14 28.2(2) . . . . ?
C11 C12 C9 N2 -1.05(17) . . . . ?
C11 C12 C9 C8 178.60(14) . . . . ?
C11 C10 C19 C18 0.0(2) . . . . ?
C11 C16 C15 O1 155.07(15) . . . . ?
C11 C16 C15 N3 -22.9(2) . . . . ?
C11 C16 C17 C18 0.4(2) . . . . ?
C13 C12 C11 C10 -173.69(13) . . . . ?
C13 C12 C11 C16 9.7(2) . . . . ?
C13 C12 C9 N2 172.36(13) . . . . ?
C13 C12 C9 C8 -8.0(3) . . . . ?
C10 N2 C9 C12 1.75(17) . . . . ?
C10 N2 C9 C8 -177.94(13) . . . . ?
C10 C11 C16 C15 -174.28(13) . . . . ?
C10 C11 C16 C17 0.6(2) . . . . ?
C9 N2 C10 C11 -1.72(15) . . . . ?
C9 N2 C10 C19 177.29(15) . . . . ?
C9 C12 C11 C10 -0.01(16) . . . . ?
C9 C12 C11 C16 -176.58(15) . . . . ?
C9 C12 C13 C14 -144.14(16) . . . . ?
C9 C8 C6 C4 178.48(13) . . . . ?
C9 C8 C7 C5 -177.26(14) . . . . ?
C16 C11 C10 N2 178.28(12) . . . . ?
C16 C11 C10 C19 -0.8(2) . . . . ?
C15 N3 C14 C13 71.5(2) . . . . ?
C15 C16 C17 C18 175.65(13) . . . . ?
C5 C3 C2 N1 -104.14(17) . . . . ?
C4 C3 C2 N1 74.48(19) . . . . ?
C6 C8 C9 N2 -32.1(2) . . . . ?
C6 C8 C9 C12 148.33(16) . . . . ?
C6 C8 C7 C5 1.1(2) . . . . ?
C6 C4 C3 C5 0.9(2) . . . . ?
C6 C4 C3 C2 -177.76(14) . . . . ?
C3 C5 C7 C8 -1.3(2) . . . . ?
C3 C4 C6 C8 -1.1(2) . . . . ?
C14 N3 C15 O1 171.59(15) . . . . ?
C14 N3 C15 C16 -10.5(2) . . . . ?
C19 C18 C17 C16 -1.4(2) . . . . ?
C17 C16 C15 O1 -19.9(2) . . . . ?
C17 C16 C15 N3 162.20(15) . . . . ?
C17 C18 C19 C10 1.2(2) . . . . ?
C20 C20 C21 O2 -177.3(2) 3_776 . . . ?
C20 C20 C21 O3 3.5(3) 3_776 . . . ?
C7 C8 C9 N2 146.23(15) . . . . ?
C7 C8 C9 C12 -33.4(2) . . . . ?
C7 C8 C6 C4 0.1(2) . . . . ?
C7 C5 C3 C4 0.3(2) . . . . ?
C7 C5 C3 C2 178.98(14) . . . . ?
C1 N1 C2 C3 -177.66(16) . . . . ?

_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
####################################################################### 
# 
# 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_rucaparib_adipic_acid
_database_code_depnum_ccdc_archive 'CCDC 2151639'
loop_
_audit_author_name
_audit_author_address
'Chao Wu'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-08-21 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-08-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 F N3 O, C6 H9 O4'
_chemical_formula_sum            'C25 H28 F N3 O5'
_chemical_formula_weight         469.50
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
F F 0.0727 0.0534 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   26.6114(5)
_cell_length_b                   15.8766(3)
_cell_length_c                   5.42780(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2293.24(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6771
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.9660
_cell_measurement_theta_min      3.1930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31282
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle-shaped
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8754
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.274
_diffrn_reflns_theta_min         3.241
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00   9.00   0.50    0.50    --    0.00  57.00  60.00   52
  2  ω     64.00  89.00   0.50    0.50    --    0.00  57.00  60.00   50
  3  ω    -47.00 -19.00   0.50    0.50    --    0.00 -57.00 -90.00   56
  4  ω    -89.00 -59.00   0.50    0.50    --    0.00 -57.00 -90.00   60
  5  ω    -77.00 -41.00   0.50    0.50    --    0.00 -19.00   0.00   72
  6  ω    106.00 132.00   0.50    5.00    --  106.20 -45.00-120.00   52
  7  ω     17.00 136.00   0.50    5.00    --  106.20 -61.00  60.00  238
  8  ω     85.00 111.00   0.50    5.00    --  106.20 -77.00-150.00   52
  9  ω    170.00 195.00   0.50    5.00    --  106.20  45.00 -90.00   50
 10  ω     78.00 140.00   0.50    5.00    --  106.20  45.00 -90.00  124
 11  ω     20.00  72.00   0.50    5.00    --  106.20 -77.00-150.00  104
 12  ω     57.00 133.00   0.50    5.00    --  106.20 -45.00-150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0983066000
_diffrn_orient_matrix_UB_12      -0.0541082000
_diffrn_orient_matrix_UB_13      0.0082677000
_diffrn_orient_matrix_UB_21      0.0969070000
_diffrn_orient_matrix_UB_22      -0.0024261000
_diffrn_orient_matrix_UB_23      0.0910513000
_diffrn_orient_matrix_UB_31      -0.2480576000
_diffrn_orient_matrix_UB_32      0.0204828000
_diffrn_orient_matrix_UB_33      0.0323779000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.820
_reflns_number_gt                4351
_reflns_number_total             4526
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.22(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.075
_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/[σ²(Fo²)+(0.0589P)²+1.2171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1293
_refine_special_details          ?
_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), C13(H13A,H13B), C14(H14A,H14B), C23(H23A,H23B),
 C22(H22A,H22B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H5), C5(H8), C7(H7), C19(H19), C17(H17)
2.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.49374(8) 0.88258(14) -0.2084(4) 0.0515(6) Uani 1 1 d . . . . .
O4 O 0.19893(9) 0.56047(15) 0.9099(4) 0.0372(5) Uani 1 1 d . . . . .
O1 O 0.43832(8) 0.71654(16) 0.5147(5) 0.0411(5) Uani 1 1 d . . . . .
O5 O 0.16592(9) 0.47617(16) 1.1868(4) 0.0403(5) Uani 1 1 d . . . . .
N2 N 0.64338(9) 0.79818(16) 0.2280(5) 0.0292(5) Uani 1 1 d . . . . .
O2 O 0.38055(10) 0.6764(2) 0.8829(6) 0.0545(7) Uani 1 1 d . . . . .
N1 N 0.86043(9) 0.55945(16) 0.6514(5) 0.0299(5) Uani 1 1 d . . . . .
N3 N 0.50116(10) 0.62777(17) 0.6069(6) 0.0377(6) Uani 1 1 d . . . . .
O3 O 0.43016(12) 0.56924(17) 0.9909(7) 0.0626(8) Uani 1 1 d . . . . .
C25 C 0.19672(11) 0.53320(18) 1.1262(5) 0.0294(6) Uani 1 1 d . . . . .
C8 C 0.70109(10) 0.72138(17) 0.5048(5) 0.0270(6) Uani 1 1 d . . . . .
C10 C 0.59369(11) 0.80025(18) 0.1662(6) 0.0290(6) Uani 1 1 d . . . . .
C11 C 0.56761(11) 0.74319(17) 0.3206(5) 0.0278(6) Uani 1 1 d . . . . .
C3 C 0.79896(11) 0.67597(18) 0.6523(6) 0.0290(6) Uani 1 1 d . . . . .
C4 C 0.79094(10) 0.71934(19) 0.4318(5) 0.0291(6) Uani 1 1 d . . . . .
H4 H 0.818752 0.733662 0.330400 0.035 Uiso 1 1 calc R U . . .
C12 C 0.60443(11) 0.70497(17) 0.4778(6) 0.0280(6) Uani 1 1 d . . . . .
C6 C 0.74298(11) 0.74158(18) 0.3599(5) 0.0274(6) Uani 1 1 d . . . . .
H5 H 0.738290 0.771116 0.209384 0.033 Uiso 1 1 calc R U . . .
C2 C 0.85126(11) 0.64901(19) 0.7231(6) 0.0314(6) Uani 1 1 d . . . . .
H2A H 0.876102 0.685768 0.640206 0.038 Uiso 1 1 calc R U . . .
H2B H 0.855695 0.655279 0.903268 0.038 Uiso 1 1 calc R U . . .
C9 C 0.65034(11) 0.74089(18) 0.4169(5) 0.0273(6) Uani 1 1 d . . . . .
C5 C 0.75794(11) 0.65836(18) 0.8009(5) 0.0295(6) Uani 1 1 d . . . . .
H8 H 0.762947 0.630041 0.953105 0.035 Uiso 1 1 calc R U . . .
C7 C 0.70969(11) 0.68134(19) 0.7313(6) 0.0302(6) Uani 1 1 d . . . . .
H7 H 0.682223 0.669864 0.837947 0.036 Uiso 1 1 calc R U . . .
C16 C 0.51470(11) 0.73732(18) 0.2981(6) 0.0313(6) Uani 1 1 d . . . . .
C19 C 0.56991(12) 0.8478(2) -0.0158(6) 0.0338(6) Uani 1 1 d . . . . .
H19 H 0.587936 0.885116 -0.120299 0.041 Uiso 1 1 calc R U . . .
C17 C 0.49105(11) 0.7847(2) 0.1168(6) 0.0365(7) Uani 1 1 d . . . . .
H17 H 0.455666 0.780971 0.096224 0.044 Uiso 1 1 calc R U . . .
C15 C 0.48244(11) 0.6920(2) 0.4789(7) 0.0347(7) Uani 1 1 d . . . . .
C18 C 0.51905(13) 0.8374(2) -0.0345(6) 0.0370(7) Uani 1 1 d . . . . .
C24 C 0.23364(14) 0.5666(2) 1.3171(6) 0.0388(7) Uani 1 1 d . . . . .
H24A H 0.216171 0.573065 1.477011 0.047 Uiso 1 1 calc R U . . .
H24B H 0.245656 0.622922 1.265247 0.047 Uiso 1 1 calc R U . . .
C1 C 0.91405(12) 0.5349(2) 0.6726(7) 0.0404(7) Uani 1 1 d . . . . .
H1C H 0.934581 0.572113 0.569658 0.061 Uiso 1 1 calc R U . . .
H1D H 0.918197 0.476510 0.617390 0.061 Uiso 1 1 calc R U . . .
H1E H 0.924776 0.539746 0.844716 0.061 Uiso 1 1 calc R U . . .
C13 C 0.59441(11) 0.63242(19) 0.6478(7) 0.0341(7) Uani 1 1 d . . . . .
H13A H 0.588977 0.653815 0.817021 0.041 Uiso 1 1 calc R U . . .
H13B H 0.623995 0.594637 0.650544 0.041 Uiso 1 1 calc R U . . .
C14 C 0.54833(12) 0.5831(2) 0.5648(7) 0.0389(8) Uani 1 1 d . . . . .
H14A H 0.551491 0.570523 0.386823 0.047 Uiso 1 1 calc R U . . .
H14B H 0.547360 0.528780 0.654182 0.047 Uiso 1 1 calc R U . . .
C20 C 0.39175(13) 0.6105(2) 1.0196(8) 0.0454(8) Uani 1 1 d . . . . .
C23 C 0.27893(13) 0.5077(2) 1.3499(6) 0.0422(8) Uani 1 1 d . . . . .
H23A H 0.293511 0.517309 1.515312 0.051 Uiso 1 1 calc R U . . .
H23B H 0.266887 0.448712 1.344127 0.051 Uiso 1 1 calc R U . . .
C22 C 0.32057(13) 0.5186(2) 1.1569(7) 0.0419(8) Uani 1 1 d . . . . .
H22A H 0.341194 0.466720 1.150262 0.050 Uiso 1 1 calc R U . . .
H22B H 0.305186 0.526965 0.992617 0.050 Uiso 1 1 calc R U . . .
C21 C 0.35378(15) 0.5925(3) 1.2163(8) 0.0529(10) Uani 1 1 d . . . . .
H21A H 0.332534 0.643048 1.240372 0.063 Uiso 1 1 calc R U . . .
H21B H 0.371559 0.581330 1.373183 0.063 Uiso 1 1 calc R U . . .
H1B H 0.8519(11) 0.5508(19) 0.495(7) 0.016(7) Uiso 1 1 d . . . . .
H1A H 0.8390(15) 0.522(3) 0.739(8) 0.041(10) Uiso 1 1 d . . . . .
H3 H 0.4817(15) 0.612(3) 0.735(8) 0.043(11) Uiso 1 1 d . . . . .
H2C H 0.4028(17) 0.690(3) 0.776(9) 0.050(12) Uiso 1 1 d . . . . .
H2 H 0.6675(18) 0.834(3) 0.159(10) 0.063(13) Uiso 1 1 d . . . . .


_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
F1 C18 1.363(4) . ?
O4 C25 1.252(4) . ?
O1 C15 1.252(4) . ?
O5 C25 1.265(4) . ?
N2 C10 1.365(4) . ?
N2 C9 1.383(4) . ?
N2 H2 0.93(5) . ?
O2 C20 1.317(5) . ?
O2 H2C 0.86(5) . ?
N1 C2 1.494(4) . ?
N1 C1 1.484(4) . ?
N1 H1B 0.89(4) . ?
N1 H1A 0.95(4) . ?
N3 C15 1.331(4) . ?
N3 C14 1.460(4) . ?
N3 H3 0.90(4) . ?
O3 C20 1.224(5) . ?
C25 C24 1.523(4) . ?
C8 C6 1.401(4) . ?
C8 C9 1.465(4) . ?
C8 C7 1.403(4) . ?
C10 C11 1.416(4) . ?
C10 C19 1.395(4) . ?
C11 C12 1.434(4) . ?
C11 C16 1.416(4) . ?
C3 C4 1.397(4) . ?
C3 C2 1.506(4) . ?
C3 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C4 C6 1.380(4) . ?
C12 C9 1.388(4) . ?
C12 C13 1.500(4) . ?
C6 H5 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C5 H8 0.9500 . ?
C5 C7 1.387(4) . ?
C7 H7 0.9500 . ?
C16 C17 1.389(5) . ?
C16 C15 1.489(4) . ?
C19 H19 0.9500 . ?
C19 C18 1.367(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C23 1.536(5) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.523(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C20 C21 1.497(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C22 1.535(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C21 1.505(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 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
C10 N2 C9 109.1(2) . . ?
C10 N2 H2 124(3) . . ?
C9 N2 H2 127(3) . . ?
C20 O2 H2C 115(3) . . ?
C2 N1 H1B 111(2) . . ?
C2 N1 H1A 111(2) . . ?
C1 N1 C2 112.8(2) . . ?
C1 N1 H1B 106(2) . . ?
C1 N1 H1A 112(2) . . ?
H1B N1 H1A 103(3) . . ?
C15 N3 C14 127.8(3) . . ?
C15 N3 H3 114(3) . . ?
C14 N3 H3 118(3) . . ?
O4 C25 O5 121.5(3) . . ?
O4 C25 C24 119.1(3) . . ?
O5 C25 C24 119.4(3) . . ?
C6 C8 C9 120.1(3) . . ?
C6 C8 C7 117.8(3) . . ?
C7 C8 C9 122.1(3) . . ?
N2 C10 C11 108.3(3) . . ?
N2 C10 C19 128.8(3) . . ?
C19 C10 C11 122.9(3) . . ?
C10 C11 C12 106.7(2) . . ?
C10 C11 C16 118.6(3) . . ?
C16 C11 C12 134.7(3) . . ?
C4 C3 C2 120.0(3) . . ?
C5 C3 C4 118.5(3) . . ?
C5 C3 C2 121.5(3) . . ?
C3 C4 H4 119.7 . . ?
C6 C4 C3 120.6(3) . . ?
C6 C4 H4 119.7 . . ?
C11 C12 C13 124.7(3) . . ?
C9 C12 C11 106.6(2) . . ?
C9 C12 C13 128.2(3) . . ?
C8 C6 H5 119.4 . . ?
C4 C6 C8 121.2(3) . . ?
C4 C6 H5 119.4 . . ?
N1 C2 C3 110.8(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N2 C9 C8 120.2(3) . . ?
N2 C9 C12 109.2(2) . . ?
C12 C9 C8 130.3(3) . . ?
C3 C5 H8 119.4 . . ?
C3 C5 C7 121.2(3) . . ?
C7 C5 H8 119.4 . . ?
C8 C7 H7 119.7 . . ?
C5 C7 C8 120.6(3) . . ?
C5 C7 H7 119.7 . . ?
C11 C16 C15 123.2(3) . . ?
C17 C16 C11 118.4(3) . . ?
C17 C16 C15 117.9(3) . . ?
C10 C19 H19 122.1 . . ?
C18 C19 C10 115.9(3) . . ?
C18 C19 H19 122.1 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
O1 C15 N3 120.6(3) . . ?
O1 C15 C16 119.5(3) . . ?
N3 C15 C16 119.9(3) . . ?
F1 C18 C19 118.5(3) . . ?
F1 C18 C17 117.5(3) . . ?
C19 C18 C17 124.0(3) . . ?
C25 C24 H24A 109.2 . . ?
C25 C24 H24B 109.2 . . ?
C25 C24 C23 111.9(3) . . ?
H24A C24 H24B 107.9 . . ?
C23 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
N1 C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 C14 110.9(3) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
N3 C14 C13 113.3(3) . . ?
N3 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
O2 C20 C21 113.6(3) . . ?
O3 C20 O2 122.8(4) . . ?
O3 C20 C21 123.5(4) . . ?
C24 C23 H23A 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C22 C23 C24 114.7(3) . . ?
C22 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C21 C22 C23 111.4(3) . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C20 C21 C22 113.1(3) . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C25 C24 C23 -97.2(3) . . . . ?
O5 C25 C24 C23 80.0(4) . . . . ?
N2 C10 C11 C12 -1.0(3) . . . . ?
N2 C10 C11 C16 177.1(3) . . . . ?
N2 C10 C19 C18 -179.4(3) . . . . ?
O2 C20 C21 C22 104.3(4) . . . . ?
O3 C20 C21 C22 -77.1(5) . . . . ?
C25 C24 C23 C22 82.1(3) . . . . ?
C10 N2 C9 C8 175.0(3) . . . . ?
C10 N2 C9 C12 0.3(3) . . . . ?
C10 C11 C12 C9 1.1(3) . . . . ?
C10 C11 C12 C13 -171.6(3) . . . . ?
C10 C11 C16 C17 3.2(4) . . . . ?
C10 C11 C16 C15 -168.4(3) . . . . ?
C10 C19 C18 F1 179.7(3) . . . . ?
C10 C19 C18 C17 1.1(5) . . . . ?
C11 C10 C19 C18 1.2(5) . . . . ?
C11 C12 C9 N2 -0.9(3) . . . . ?
C11 C12 C9 C8 -174.9(3) . . . . ?
C11 C12 C13 C14 22.2(4) . . . . ?
C11 C16 C17 C18 -1.2(4) . . . . ?
C11 C16 C15 O1 149.7(3) . . . . ?
C11 C16 C15 N3 -28.0(5) . . . . ?
C3 C4 C6 C8 -0.1(4) . . . . ?
C3 C5 C7 C8 1.6(4) . . . . ?
C4 C3 C2 N1 -96.6(3) . . . . ?
C4 C3 C5 C7 1.4(4) . . . . ?
C12 C11 C16 C17 -179.3(3) . . . . ?
C12 C11 C16 C15 9.0(5) . . . . ?
C12 C13 C14 N3 -72.0(4) . . . . ?
C6 C8 C9 N2 -17.4(4) . . . . ?
C6 C8 C9 C12 156.1(3) . . . . ?
C6 C8 C7 C5 -3.7(4) . . . . ?
C2 C3 C4 C6 177.5(3) . . . . ?
C2 C3 C5 C7 -178.2(3) . . . . ?
C9 N2 C10 C11 0.5(3) . . . . ?
C9 N2 C10 C19 -179.0(3) . . . . ?
C9 C8 C6 C4 -176.1(3) . . . . ?
C9 C8 C7 C5 175.4(3) . . . . ?
C9 C12 C13 C14 -149.0(3) . . . . ?
C5 C3 C4 C6 -2.2(4) . . . . ?
C5 C3 C2 N1 83.0(3) . . . . ?
C7 C8 C6 C4 3.0(4) . . . . ?
C7 C8 C9 N2 163.6(3) . . . . ?
C7 C8 C9 C12 -23.0(5) . . . . ?
C16 C11 C12 C9 -176.5(3) . . . . ?
C16 C11 C12 C13 10.7(5) . . . . ?
C16 C17 C18 F1 -179.8(3) . . . . ?
C16 C17 C18 C19 -1.1(5) . . . . ?
C19 C10 C11 C12 178.5(3) . . . . ?
C19 C10 C11 C16 -3.4(4) . . . . ?
C17 C16 C15 O1 -22.0(4) . . . . ?
C17 C16 C15 N3 160.2(3) . . . . ?
C15 N3 C14 C13 75.6(5) . . . . ?
C15 C16 C17 C18 171.0(3) . . . . ?
C24 C23 C22 C21 80.3(4) . . . . ?
C1 N1 C2 C3 168.9(3) . . . . ?
C13 C12 C9 N2 171.5(3) . . . . ?
C13 C12 C9 C8 -2.5(5) . . . . ?
C14 N3 C15 O1 170.0(3) . . . . ?
C14 N3 C15 C16 -12.3(5) . . . . ?
C23 C22 C21 C20 -174.3(3) . . . . ?

_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 2.588
_oxdiff_exptl_absorpt_empirical_full_min 0.298
####################################################################### 
# 
# 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_rucaparib_pimelic_acid
_database_code_depnum_ccdc_archive 'CCDC 2151640'
loop_
_audit_author_name
_audit_author_address
'Chao Wu'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-08-21 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-08-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 F N3 O, C7 H11 O4'
_chemical_formula_sum            'C26 H30 F N3 O5'
_chemical_formula_weight         483.53
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
F F 0.0727 0.0534 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   27.4657(3)
_cell_length_b                   15.6448(2)
_cell_length_c                   5.56040(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2389.28(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17827
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.9970
_cell_measurement_theta_min      3.1940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  70.00   0.50    1.50    --    0.00  57.00  60.00  196
  2  ω     12.00  38.00   0.50    1.50    --    0.00  57.00-120.00   52
  3  ω    -88.00 -62.00   0.50    1.50    --    0.00 -37.00  90.00   52
  4  ω    -39.00  47.00   0.50    1.50    --    0.00 -19.00-120.00  172
  5  ω    -26.00  71.00   0.50    1.50    --    0.00  57.00 120.00  194
  6  ω    -43.00 -17.00   0.50    1.50    --    0.00 -37.00  90.00   52
  7  ω     62.00  88.00   0.50    2.50    --  106.20 -77.00 -30.00   52
  8  ω     91.00 117.00   0.50    2.50    --  106.20 -30.00-180.00   52
  9  ω     60.00  98.00   0.50    2.50    --  106.20 -45.00 -30.00   76
 10  ω     22.00  50.00   0.50    2.50    --  106.20 -30.00-180.00   56
 11  ω     74.00 122.00   0.50    2.50    --  106.20 -82.00  90.00   96
 12  ω    165.00 192.00   0.50    2.50    --  106.20  45.00 -90.00   54
 13  ω     57.00 143.00   0.50    2.50    --  106.20 -82.00  30.00  172
 14  ω     47.00 143.00   0.50    2.50    --  106.20 -82.00 -30.00  192
 15  ω     78.00 195.00   0.50    2.50    --  106.20  45.00 150.00  234
 16  ω     85.00 193.00   0.50    2.50    --  106.20  82.00-120.00  216
 17  ω     57.00 106.00   0.50    2.50    --  106.20 -82.00 150.00   98
 18  ω     67.00 143.00   0.50    2.50    --  106.20 -82.00-150.00  152
 19  ω    125.00 189.00   0.50    2.50    --  106.20  45.00  30.00  128
 20  ω     18.00  71.00   0.50    2.50    --  106.20 -45.00 150.00  106
 21  ω     77.00 102.00   0.50    2.50    --  106.20 -45.00 150.00   50
 22  ω     94.00 131.00   0.50    2.50    --  106.20 -82.00 -90.00   74
 23  ω     78.00 115.00   0.50    2.50    --  106.20  45.00  30.00   74
 24  ω     73.00 134.00   0.50    2.50    --  106.20 -45.00-150.00  122
 25  ω     79.00 192.00   0.50    2.50    --  106.20  30.00 -90.00  226
 26  ω    101.00 184.00   0.50    2.50    --  106.20  45.00 -30.00  166
 27  ω     27.00  52.00   0.50    2.50    --  106.20 -45.00 -30.00   50
 28  ω     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       'ω 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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_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_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.129
_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/[σ²(Fo²)+(0.0746P)²+0.2256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1255
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.49702(7) 0.88218(13) -0.1807(4) 0.0494(5) Uani 1 1 d . . . . .
O4 O 0.81398(7) 0.54008(11) 0.8887(3) 0.0286(4) Uani 1 1 d . . . . .
O5 O 0.85072(7) 0.45979(12) 1.1608(3) 0.0310(4) Uani 1 1 d . . . . .
O1 O 0.54525(6) 0.71465(14) 0.5274(4) 0.0398(5) Uani 1 1 d . . . . .
O2 O 0.60140(7) 0.68076(15) 0.8860(5) 0.0447(5) Uani 1 1 d . . . . .
N1 N 0.12924(7) 0.57197(13) 0.6208(4) 0.0226(4) Uani 1 1 d . . . . .
O3 O 0.55145(7) 0.57734(13) 1.0122(5) 0.0434(5) Uani 1 1 d . . . . .
N2 N 0.34856(7) 0.79445(13) 0.2113(4) 0.0259(4) Uani 1 1 d . . . . .
N3 N 0.48399(8) 0.62448(15) 0.6167(5) 0.0345(5) Uani 1 1 d . . . . .
C26 C 0.82087(8) 0.51743(15) 1.1036(5) 0.0242(5) Uani 1 1 d . . . . .
C3 C 0.19304(8) 0.68308(14) 0.6074(4) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.29023(8) 0.71880(14) 0.4729(4) 0.0222(5) Uani 1 1 d . . . . .
C9 C 0.34032(8) 0.73644(14) 0.3948(4) 0.0225(4) Uani 1 1 d . . . . .
C10 C 0.39727(8) 0.79772(16) 0.1626(5) 0.0260(5) Uani 1 1 d . . . . .
C5 C 0.23153(8) 0.66294(15) 0.7589(4) 0.0244(5) Uani 1 1 d . . . . .
H5 H 0.225052 0.636149 0.908888 0.029 Uiso 1 1 calc R U . . .
C6 C 0.25108(8) 0.73940(15) 0.3219(5) 0.0239(5) Uani 1 1 d . . . . .
H6 H 0.257358 0.765688 0.171065 0.029 Uiso 1 1 calc R U . . .
C12 C 0.38418(8) 0.70052(15) 0.4638(5) 0.0247(5) Uani 1 1 d . . . . .
C11 C 0.42126(8) 0.73943(15) 0.3178(5) 0.0251(5) Uani 1 1 d . . . . .
C4 C 0.20347(8) 0.72229(15) 0.3878(5) 0.0243(5) Uani 1 1 d . . . . .
H4 H 0.177619 0.737385 0.282518 0.029 Uiso 1 1 calc R U . . .
C2 C 0.14110(8) 0.66259(15) 0.6774(5) 0.0246(5) Uani 1 1 d . . . . .
H2A H 0.136658 0.672802 0.851751 0.029 Uiso 1 1 calc R U . . .
H2B H 0.118576 0.700803 0.589294 0.029 Uiso 1 1 calc R U . . .
C7 C 0.27947(8) 0.68127(15) 0.6954(5) 0.0251(5) Uani 1 1 d . . . . .
H7 H 0.305109 0.668202 0.804004 0.030 Uiso 1 1 calc R U . . .
C15 C 0.50258(9) 0.68893(17) 0.4890(6) 0.0315(5) Uani 1 1 d . . . . .
C16 C 0.47262(9) 0.73373(16) 0.3060(5) 0.0290(5) Uani 1 1 d . . . . .
C24 C 0.74119(9) 0.58618(17) 1.2298(5) 0.0318(6) Uani 1 1 d . . . . .
H24A H 0.728394 0.629658 1.342648 0.038 Uiso 1 1 calc R U . . .
H24B H 0.740786 0.611271 1.066309 0.038 Uiso 1 1 calc R U . . .
C20 C 0.58965(9) 0.61710(17) 1.0302(6) 0.0340(6) Uani 1 1 d . . . . .
C18 C 0.47151(10) 0.83586(17) -0.0171(6) 0.0346(6) Uani 1 1 d . . . . .
C1 C 0.07724(9) 0.55084(18) 0.6629(6) 0.0340(6) Uani 1 1 d . . . . .
H1C H 0.056652 0.589489 0.568563 0.051 Uiso 1 1 calc R U . . .
H1D H 0.069690 0.557397 0.834144 0.051 Uiso 1 1 calc R U . . .
H1E H 0.071048 0.491675 0.613700 0.051 Uiso 1 1 calc R U . . .
C19 C 0.42183(9) 0.84703(17) -0.0087(6) 0.0320(5) Uani 1 1 d . . . . .
H19 H 0.405325 0.885634 -0.112347 0.038 Uiso 1 1 calc R U . . .
C14 C 0.43880(9) 0.57843(16) 0.5668(6) 0.0344(6) Uani 1 1 d . . . . .
H14A H 0.439104 0.523755 0.656373 0.041 Uiso 1 1 calc R U . . .
H14B H 0.437483 0.564717 0.393060 0.041 Uiso 1 1 calc R U . . .
C17 C 0.49711(9) 0.78213(18) 0.1340(5) 0.0337(6) Uani 1 1 d . . . . .
H17 H 0.531513 0.778153 0.120546 0.040 Uiso 1 1 calc R U . . .
C13 C 0.39300(9) 0.62836(17) 0.6351(5) 0.0308(6) Uani 1 1 d . . . . .
H13A H 0.364595 0.589414 0.633944 0.037 Uiso 1 1 calc R U . . .
H13B H 0.396657 0.651324 0.800047 0.037 Uiso 1 1 calc R U . . .
C25 C 0.79333(10) 0.5650(2) 1.2979(5) 0.0369(6) Uani 1 1 d . . . . .
H25A H 0.810786 0.618856 1.334572 0.044 Uiso 1 1 calc R U . . .
H25B H 0.793113 0.529902 1.445997 0.044 Uiso 1 1 calc R U . . .
C23 C 0.70809(10) 0.50865(17) 1.2344(6) 0.0377(6) Uani 1 1 d . . . . .
H23A H 0.700863 0.493665 1.403632 0.045 Uiso 1 1 calc R U . . .
H23B H 0.725338 0.459636 1.160738 0.045 Uiso 1 1 calc R U . . .
C22 C 0.66059(10) 0.52315(19) 1.1015(7) 0.0430(7) Uani 1 1 d . . . . .
H22A H 0.641486 0.469499 1.104655 0.052 Uiso 1 1 calc R U . . .
H22B H 0.667983 0.536361 0.931260 0.052 Uiso 1 1 calc R U . . .
C21 C 0.62917(10) 0.59548(18) 1.2052(6) 0.0363(6) Uani 1 1 d . . . . .
H21A H 0.614702 0.577210 1.359933 0.044 Uiso 1 1 calc R U . . .
H21B H 0.649610 0.646498 1.235315 0.044 Uiso 1 1 calc R U . . .
H1A H 0.1384(12) 0.559(2) 0.466(7) 0.033(8) Uiso 1 1 d . . . . .
H3 H 0.5042(15) 0.607(3) 0.741(8) 0.051(11) Uiso 1 1 d . . . . .
H2C H 0.5807(15) 0.690(2) 0.760(8) 0.056(11) Uiso 1 1 d . . . . .
H1B H 0.1476(13) 0.533(2) 0.724(7) 0.042(9) Uiso 1 1 d . . . . .
H2 H 0.3280(15) 0.835(3) 0.172(9) 0.070(13) Uiso 1 1 d . . . . .


_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
F1 C18 1.358(3) . ?
O4 C26 1.261(3) . ?
O5 C26 1.260(3) . ?
O1 C15 1.257(3) . ?
O2 C20 1.319(4) . ?
O2 H2C 0.91(4) . ?
N1 C2 1.488(3) . ?
N1 C1 1.485(3) . ?
N1 H1A 0.92(4) . ?
N1 H1B 0.97(4) . ?
O3 C20 1.224(3) . ?
N2 C9 1.384(3) . ?
N2 C10 1.366(3) . ?
N2 H2 0.88(5) . ?
N3 C15 1.335(4) . ?
N3 C14 1.462(3) . ?
N3 H3 0.93(4) . ?
C26 C25 1.515(3) . ?
C3 C5 1.388(3) . ?
C3 C4 1.396(3) . ?
C3 C2 1.513(3) . ?
C8 C9 1.469(3) . ?
C8 C6 1.402(3) . ?
C8 C7 1.401(3) . ?
C9 C12 1.384(3) . ?
C10 C11 1.418(3) . ?
C10 C19 1.399(3) . ?
C5 H5 0.9500 . ?
C5 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C6 C4 1.384(3) . ?
C12 C11 1.437(3) . ?
C12 C13 1.497(3) . ?
C11 C16 1.415(3) . ?
C4 H4 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C7 H7 0.9500 . ?
C15 C16 1.485(4) . ?
C16 C17 1.393(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.518(4) . ?
C24 C23 1.516(4) . ?
C20 C21 1.496(4) . ?
C18 C19 1.376(4) . ?
C18 C17 1.381(4) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C19 H19 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.529(4) . ?
C17 H17 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C22 1.517(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C21 1.535(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 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
C20 O2 H2C 115(3) . . ?
C2 N1 H1A 110(2) . . ?
C2 N1 H1B 111(2) . . ?
C1 N1 C2 112.92(19) . . ?
C1 N1 H1A 111(2) . . ?
C1 N1 H1B 105(2) . . ?
H1A N1 H1B 106(3) . . ?
C9 N2 H2 124(3) . . ?
C10 N2 C9 109.3(2) . . ?
C10 N2 H2 123(3) . . ?
C15 N3 C14 126.6(3) . . ?
C15 N3 H3 113(2) . . ?
C14 N3 H3 120(2) . . ?
O4 C26 C25 117.6(2) . . ?
O5 C26 O4 122.6(2) . . ?
O5 C26 C25 119.8(2) . . ?
C5 C3 C4 118.3(2) . . ?
C5 C3 C2 120.9(2) . . ?
C4 C3 C2 120.8(2) . . ?
C6 C8 C9 119.9(2) . . ?
C7 C8 C9 122.5(2) . . ?
C7 C8 C6 117.6(2) . . ?
N2 C9 C8 119.6(2) . . ?
C12 C9 N2 109.2(2) . . ?
C12 C9 C8 131.1(2) . . ?
N2 C10 C11 108.1(2) . . ?
N2 C10 C19 128.9(2) . . ?
C19 C10 C11 123.0(2) . . ?
C3 C5 H5 119.4 . . ?
C3 C5 C7 121.3(2) . . ?
C7 C5 H5 119.4 . . ?
C8 C6 H6 119.3 . . ?
C4 C6 C8 121.5(2) . . ?
C4 C6 H6 119.3 . . ?
C9 C12 C11 106.8(2) . . ?
C9 C12 C13 128.6(2) . . ?
C11 C12 C13 124.3(2) . . ?
C10 C11 C12 106.6(2) . . ?
C16 C11 C10 118.4(2) . . ?
C16 C11 C12 134.9(2) . . ?
C3 C4 H4 119.7 . . ?
C6 C4 C3 120.7(2) . . ?
C6 C4 H4 119.7 . . ?
N1 C2 C3 110.71(18) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C8 C7 H7 119.7 . . ?
C5 C7 C8 120.6(2) . . ?
C5 C7 H7 119.7 . . ?
O1 C15 N3 120.5(3) . . ?
O1 C15 C16 118.8(2) . . ?
N3 C15 C16 120.6(2) . . ?
C11 C16 C15 123.4(2) . . ?
C17 C16 C11 118.6(2) . . ?
C17 C16 C15 117.4(2) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C23 C24 C25 112.8(2) . . ?
O2 C20 C21 112.9(2) . . ?
O3 C20 O2 122.9(3) . . ?
O3 C20 C21 124.1(3) . . ?
F1 C18 C19 117.8(3) . . ?
F1 C18 C17 118.0(2) . . ?
C19 C18 C17 124.2(3) . . ?
N1 C1 H1C 109.5 . . ?
N1 C1 H1D 109.5 . . ?
N1 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C10 C19 H19 122.2 . . ?
C18 C19 C10 115.5(3) . . ?
C18 C19 H19 122.2 . . ?
N3 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
N3 C14 C13 113.6(2) . . ?
H14A C14 H14B 107.7 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C12 C13 C14 111.1(2) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C26 C25 C24 113.6(2) . . ?
C26 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
C24 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C24 C23 C22 112.8(2) . . ?
H23A C23 H23B 107.8 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C23 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C23 C22 C21 114.3(3) . . ?
H22A C22 H22B 107.6 . . ?
C21 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C20 C21 C22 109.3(3) . . ?
C20 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
C22 C21 H21A 109.8 . . ?
C22 C21 H21B 109.8 . . ?
H21A C21 H21B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C18 C19 C10 179.9(2) . . . . ?
F1 C18 C17 C16 179.5(3) . . . . ?
O4 C26 C25 C24 39.7(4) . . . . ?
O5 C26 C25 C24 -142.9(3) . . . . ?
O1 C15 C16 C11 -150.4(3) . . . . ?
O1 C15 C16 C17 20.5(4) . . . . ?
O2 C20 C21 C22 -94.1(3) . . . . ?
O3 C20 C21 C22 82.0(4) . . . . ?
N2 C9 C12 C11 0.9(3) . . . . ?
N2 C9 C12 C13 -172.7(2) . . . . ?
N2 C10 C11 C12 0.0(3) . . . . ?
N2 C10 C11 C16 -177.9(2) . . . . ?
N2 C10 C19 C18 -179.4(3) . . . . ?
N3 C15 C16 C11 27.2(4) . . . . ?
N3 C15 C16 C17 -161.9(3) . . . . ?
N3 C14 C13 C12 72.5(3) . . . . ?
C3 C5 C7 C8 -1.6(4) . . . . ?
C8 C9 C12 C11 176.8(2) . . . . ?
C8 C9 C12 C13 3.2(5) . . . . ?
C8 C6 C4 C3 -0.5(4) . . . . ?
C9 N2 C10 C11 0.6(3) . . . . ?
C9 N2 C10 C19 179.7(3) . . . . ?
C9 C8 C6 C4 178.8(2) . . . . ?
C9 C8 C7 C5 -177.8(2) . . . . ?
C9 C12 C11 C10 -0.6(3) . . . . ?
C9 C12 C11 C16 176.8(3) . . . . ?
C9 C12 C13 C14 149.8(3) . . . . ?
C10 N2 C9 C8 -177.4(2) . . . . ?
C10 N2 C9 C12 -1.0(3) . . . . ?
C10 C11 C16 C15 167.4(2) . . . . ?
C10 C11 C16 C17 -3.4(4) . . . . ?
C5 C3 C4 C6 0.9(3) . . . . ?
C5 C3 C2 N1 -82.6(3) . . . . ?
C6 C8 C9 N2 18.9(3) . . . . ?
C6 C8 C9 C12 -156.6(3) . . . . ?
C6 C8 C7 C5 2.0(3) . . . . ?
C12 C11 C16 C15 -9.8(5) . . . . ?
C12 C11 C16 C17 179.5(3) . . . . ?
C11 C10 C19 C18 -0.4(4) . . . . ?
C11 C12 C13 C14 -22.8(4) . . . . ?
C11 C16 C17 C18 1.5(4) . . . . ?
C4 C3 C5 C7 0.1(4) . . . . ?
C4 C3 C2 N1 97.0(3) . . . . ?
C2 C3 C5 C7 179.7(2) . . . . ?
C2 C3 C4 C6 -178.7(2) . . . . ?
C7 C8 C9 N2 -161.4(2) . . . . ?
C7 C8 C9 C12 23.1(4) . . . . ?
C7 C8 C6 C4 -0.9(3) . . . . ?
C15 N3 C14 C13 -76.1(4) . . . . ?
C15 C16 C17 C18 -169.8(3) . . . . ?
C24 C23 C22 C21 -61.1(4) . . . . ?
C1 N1 C2 C3 -174.2(2) . . . . ?
C19 C10 C11 C12 -179.2(3) . . . . ?
C19 C10 C11 C16 2.9(4) . . . . ?
C19 C18 C17 C16 1.1(5) . . . . ?
C14 N3 C15 O1 -168.9(3) . . . . ?
C14 N3 C15 C16 13.6(4) . . . . ?
C17 C18 C19 C10 -1.7(4) . . . . ?
C13 C12 C11 C10 173.4(2) . . . . ?
C13 C12 C11 C16 -9.2(5) . . . . ?
C25 C24 C23 C22 -163.7(3) . . . . ?
C23 C24 C25 C26 73.7(3) . . . . ?
C23 C22 C21 C20 167.2(3) . . . . ?

_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
