#------------------------------------------------------------------------------
#$Date: 2022-10-12 01:40:22 +0300 (Wed, 12 Oct 2022) $
#$Revision: 278530 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/56/7245644.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245644
loop_
_publ_author_name
'Wu, Chao'
'Gao, Lu'
'Xiong, Jing'
'Dai, Xia-Lin'
'Gao, Wei'
'Lu, Tongbu'
'Chen, Jia-Mei'
_publ_section_title
;
 Salts of rucaparib with dicarboxylic acids: synthesis, crystal structures
 and solubility aspects
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00842D
_journal_year                    2022
_chemical_formula_moiety         'C19 H19 F N3 O, C2 H O2, 2.5(H2 O)'
_chemical_formula_sum            'C21 H25 F N3 O5.5'
_chemical_formula_weight         426.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-08-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-21 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.612(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7628(4)
_cell_length_b                   9.9401(2)
_cell_length_c                   14.6764(3)
_cell_measurement_reflns_used    7579
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      79.0700
_cell_measurement_theta_min      5.4120
_cell_volume                     2090.64(9)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_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_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_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
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.057
_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_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0534
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3938
_reflns_number_total             4449
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00842d2.cif
_cod_data_source_block           rucaparib_fumaric_acid
_cod_original_formula_sum        'C21 H25 F N3 O5.50'
_cod_database_code               7245644
_shelx_shelxl_version_number     2018/3
_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.
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, 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)
;
_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
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'
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 . . . . .
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'
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_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_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) . . . . ?
