#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:53:34 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288772 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247520.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_7247520
loop_
_publ_author_name
'Zhang, Min'
'Gu, Dai-Lin'
'Zhen, Jian-Feng'
'Lu, Tong-Bu'
'Dai, Xia-Lin'
'Chen, Jia-Mei'
_publ_section_title
;
 A novel drug--drug cocrystal of tegafur and myricetin: optimized
 properties of dissolution and tabletability
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              6171
_journal_page_last               6179
_journal_paper_doi               10.1039/D3CE00794D
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C8 H9 F N2 O3, C15 H10 O8'
_chemical_formula_sum            'C23 H19 F N2 O11'
_chemical_formula_weight         518.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                109.530(2)
_cell_angle_beta                 108.436(2)
_cell_angle_gamma                100.043(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2310(2)
_cell_length_b                   11.1587(2)
_cell_length_c                   11.8072(2)
_cell_measurement_reflns_used    14055
_cell_measurement_temperature    152(5)
_cell_measurement_theta_max      78.4780
_cell_measurement_theta_min      4.3600
_cell_volume                     1032.67(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      152(5)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  89.00   0.50    0.50    --    0.00  77.00  90.00  246
  2  ω    -28.00  89.00   0.50    0.50    --    0.00  57.00 150.00  234
  3  ω     -8.00 117.00   0.50    0.50    --   28.00  82.00 -47.96  250
  4  ω     30.00 153.00   0.50    0.64    --   64.00  77.00-159.28  246
  5  ω     17.00 140.00   0.50    0.64    --  106.20 -30.00-150.00  246
  6  ω     17.00 143.00   0.50    0.64    --  106.20 -82.00   0.00  252
  7  ω     72.00 196.00   0.50    0.64    --  106.20  77.00-180.00  248
  8  ω     17.00 136.00   0.50    0.64    --  106.20 -61.00 150.00  238
  9  ω     17.00 143.00   0.50    0.64    --  106.20 -82.00 -60.00  252
 10  ω     73.00 196.00   0.50    0.64    --  106.20  30.00-120.00  246
 11  ω     17.00 143.00   0.50    0.64    --  106.20 -82.00  60.00  252
 12  ω     78.00 196.00   0.50    0.64    --  106.20  45.00 120.00  236
 13  ω     73.00 196.00   0.50    0.64    --  106.20  30.00-150.00  246
 14  ω     17.00 136.00   0.50    0.64    --  106.20 -61.00   0.00  238
 15  ω     17.00 143.00   0.50    0.64    --  106.20 -82.00 150.00  252
 16  ω     17.00 143.00   0.50    0.64    --  106.20 -82.00-120.00  252
 17  ω     17.00 136.00   0.50    0.64    --  106.20 -61.00 -60.00  238
 18  ω     17.00 143.00   0.50    0.64    --  106.20 -82.00-180.00  252
 19  ω     78.00 196.00   0.50    0.64    --  106.20  45.00-150.00  236
 20  ω     17.00 143.00   0.50    0.64    --  106.20 -82.00 -30.00  252
 21  ω     70.00 196.00   0.50    0.64    --  106.20  82.00  90.00  252
 22  ω     16.00  59.00   0.50    0.50    --   52.00  81.00 121.68   86
 23  ω     18.00 141.00   0.50    0.50    --   52.00  77.00  28.31  246
;
_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      0.1035428000
_diffrn_orient_matrix_UB_12      -0.0889689000
_diffrn_orient_matrix_UB_13      -0.0346577000
_diffrn_orient_matrix_UB_21      0.1410578000
_diffrn_orient_matrix_UB_22      0.0913618000
_diffrn_orient_matrix_UB_23      0.1329593000
_diffrn_orient_matrix_UB_31      -0.0608055000
_diffrn_orient_matrix_UB_32      -0.0867848000
_diffrn_orient_matrix_UB_33      0.0633743000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18762
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        63.691
_diffrn_reflns_theta_max         63.691
_diffrn_reflns_theta_min         4.343
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27153
_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_density_diffrn    1.667
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0460
_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)+(0.0766P)²+0.6133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3184
_reflns_number_total             3393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00794d2.cif
_cod_data_source_block           tgf-yms
_cod_depositor_comments          'Adding full bibliography for 7247520.cif.'
_cod_database_code               7247520
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.888
_reflns_odcompleteness_completeness 99.31
_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, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C19(H19), C13(H13), C2(H2A), C9(H9A), C18(H18)
2.d Idealised tetrahedral OH refined as rotating group:
 O10(H10), O4(H4), O9(H9), O7(H7), O5(H5), O11(H11)
;
_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 4.524
_oxdiff_exptl_absorpt_empirical_full_min 0.300
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.84793(14) 0.56437(12) 0.04746(12) 0.0307(3) Uani 1 1 d . . . . .
O6 O 0.87522(15) 0.66714(13) 0.44170(12) 0.0198(3) Uani 1 1 d . . . . .
O10 O 1.17237(15) 1.10106(13) 0.28507(13) 0.0211(3) Uani 1 1 d . . . . .
H10 H 1.264811 1.151797 0.328557 0.032 Uiso 1 1 calc GR . . . .
O4 O 0.89646(16) 0.45938(14) 0.73956(13) 0.0229(3) Uani 1 1 d . . . . .
H4 H 0.988336 0.511505 0.776139 0.034 Uiso 1 1 calc GR . . . .
O9 O 0.86315(15) 0.91670(14) 0.18313(13) 0.0239(3) Uani 1 1 d . . . . .
H9 H 0.891653 0.975757 0.160814 0.036 Uiso 1 1 calc GR . . . .
O7 O 1.27193(16) 0.83133(14) 0.70772(13) 0.0243(3) Uani 1 1 d . . . . .
H7 H 1.306642 0.815867 0.772641 0.036 Uiso 1 1 calc GR . . . .
O5 O 0.43536(16) 0.30712(14) 0.34848(14) 0.0258(3) Uani 1 1 d . . . . .
H5 H 0.399291 0.320765 0.282585 0.039 Uiso 1 1 calc GR . . . .
O8 O 1.14215(16) 0.65460(13) 0.78172(12) 0.0219(3) Uani 1 1 d . . . . .
O11 O 1.40902(16) 1.10226(14) 0.48926(14) 0.0270(3) Uani 1 1 d . . . . .
H11 H 1.470139 1.103490 0.557656 0.040 Uiso 1 1 calc GR . . . .
O2 O 0.70155(16) 0.65506(14) -0.13519(13) 0.0261(3) Uani 1 1 d . . . . .
O1 O 1.18261(17) 0.95467(14) -0.02162(14) 0.0263(3) Uani 1 1 d . . . . .
O3 O 1.40774(17) 0.81439(15) 0.24688(13) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.94573(19) 0.80207(16) -0.07770(15) 0.0203(4) Uani 1 1 d . . . . .
H2 H 0.899712 0.831009 -0.134019 0.024 Uiso 1 1 calc R . . . .
N1 N 1.18289(18) 0.81117(15) 0.07804(15) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.8078(2) 0.57582(18) 0.47836(18) 0.0171(4) Uani 1 1 d . . . . .
C12 C 0.8171(2) 0.47092(18) 0.62802(18) 0.0177(4) Uani 1 1 d . . . . .
C21 C 1.2597(2) 1.01489(19) 0.44879(19) 0.0193(4) Uani 1 1 d . . . . .
C15 C 1.0293(2) 0.75388(18) 0.51625(18) 0.0178(4) Uani 1 1 d . . . . .
C00J C 1.0719(2) 0.84319(18) 0.45671(18) 0.0172(4) Uani 1 1 d . . . . .
C11 C 0.8933(2) 0.56859(18) 0.59585(18) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.5845(2) 0.39597(18) 0.42823(19) 0.0201(4) Uani 1 1 d . . . . .
C22 C 1.1400(2) 1.01553(18) 0.34114(18) 0.0171(4) Uani 1 1 d . . . . .
C16 C 1.1179(2) 0.74902(18) 0.62986(18) 0.0179(4) Uani 1 1 d . . . . .
C20 C 0.9861(2) 0.92726(18) 0.29023(17) 0.0173(4) Uani 1 1 d . . . . .
C19 C 1.2280(2) 0.93054(19) 0.50675(18) 0.0202(4) Uani 1 1 d . . . . .
H19 H 1.309217 0.931665 0.578268 0.024 Uiso 1 1 calc R . . . .
C4 C 0.8477(2) 0.70157(19) -0.06776(18) 0.0198(4) Uani 1 1 d . . . . .
C13 C 0.6631(2) 0.38599(18) 0.54529(19) 0.0198(4) Uani 1 1 d . . . . .
H13 H 0.612435 0.322978 0.567304 0.024 Uiso 1 1 calc R . . . .
C17 C 1.0551(2) 0.65553(18) 0.67628(17) 0.0166(4) Uani 1 1 d . . . . .
C3 C 0.9350(2) 0.65937(19) 0.02783(18) 0.0202(4) Uani 1 1 d . . . . .
C1 C 1.1102(2) 0.86196(19) -0.00727(18) 0.0198(4) Uani 1 1 d . . . . .
C2 C 1.0937(2) 0.71267(19) 0.09676(19) 0.0206(4) Uani 1 1 d . . . . .
H2A H 1.144970 0.682801 0.158458 0.025 Uiso 1 1 calc R . . . .
C9 C 0.6538(2) 0.49069(19) 0.39320(18) 0.0199(4) Uani 1 1 d . . . . .
H9A H 0.599059 0.496856 0.315393 0.024 Uiso 1 1 calc R . . . .
C18 C 0.9535(2) 0.84128(18) 0.34727(18) 0.0187(4) Uani 1 1 d . . . . .
H18 H 0.850671 0.781206 0.311853 0.022 Uiso 1 1 calc R . . . .
C5 C 1.3622(2) 0.8734(2) 0.1588(2) 0.0254(4) Uani 1 1 d . . . . .
H5A H 1.389031 0.970341 0.206969 0.030 Uiso 1 1 calc R . . . .
C6 C 1.4569(2) 0.8441(2) 0.0747(2) 0.0306(5) Uani 1 1 d . . . . .
H6A H 1.563679 0.908855 0.117479 0.037 Uiso 1 1 calc R . . . .
H6B H 1.401874 0.843634 -0.010461 0.037 Uiso 1 1 calc R . . . .
C8 C 1.4701(3) 0.7060(2) 0.1917(2) 0.0353(5) Uani 1 1 d . . . . .
H8A H 1.404026 0.620699 0.178634 0.042 Uiso 1 1 calc R . . . .
H8B H 1.579585 0.722819 0.250421 0.042 Uiso 1 1 calc R . . . .
C7 C 1.4642(3) 0.7048(2) 0.0621(2) 0.0346(5) Uani 1 1 d . . . . .
H7A H 1.369746 0.635706 -0.010624 0.041 Uiso 1 1 calc R . . . .
H7B H 1.559508 0.690199 0.049205 0.041 Uiso 1 1 calc R . . . .
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 O6 C15 122.03(14) . . ?
C22 O10 H10 109.5 . . ?
C12 O4 H4 109.5 . . ?
C20 O9 H9 109.5 . . ?
C16 O7 H7 109.5 . . ?
C14 O5 H5 109.5 . . ?
C21 O11 H11 109.5 . . ?
C5 O3 C8 109.50(16) . . ?
C4 N2 H2 116.3 . . ?
C4 N2 C1 127.34(16) . . ?
C1 N2 H2 116.3 . . ?
C1 N1 C2 120.89(16) . . ?
C1 N1 C5 118.15(15) . . ?
C2 N1 C5 120.81(15) . . ?
O6 C10 C11 120.63(16) . . ?
O6 C10 C9 116.86(16) . . ?
C9 C10 C11 122.50(17) . . ?
O4 C12 C11 119.77(16) . . ?
O4 C12 C13 119.68(16) . . ?
C13 C12 C11 120.54(17) . . ?
O11 C21 C22 114.73(16) . . ?
O11 C21 C19 123.56(17) . . ?
C19 C21 C22 121.70(17) . . ?
O6 C15 C00J 111.29(15) . . ?
C16 C15 O6 119.44(16) . . ?
C16 C15 C00J 129.25(17) . . ?
C19 C00J C15 121.88(16) . . ?
C18 C00J C15 119.03(17) . . ?
C18 C00J C19 119.09(17) . . ?
C10 C11 C12 117.94(17) . . ?
C10 C11 C17 119.55(17) . . ?
C12 C11 C17 122.47(17) . . ?
O5 C14 C13 116.67(16) . . ?
O5 C14 C9 120.98(17) . . ?
C9 C14 C13 122.35(17) . . ?
O10 C22 C21 121.29(16) . . ?
O10 C22 C20 119.74(16) . . ?
C20 C22 C21 118.98(17) . . ?
O7 C16 C17 115.55(16) . . ?
C15 C16 O7 122.40(17) . . ?
C15 C16 C17 122.05(16) . . ?
O9 C20 C22 123.49(16) . . ?
O9 C20 C18 116.81(16) . . ?
C18 C20 C22 119.67(17) . . ?
C21 C19 C00J 119.25(17) . . ?
C21 C19 H19 120.4 . . ?
C00J C19 H19 120.4 . . ?
O2 C4 N2 122.32(17) . . ?
O2 C4 C3 125.33(18) . . ?
N2 C4 C3 112.35(16) . . ?
C12 C13 C14 119.10(17) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
O8 C17 C11 124.12(17) . . ?
O8 C17 C16 119.60(16) . . ?
C11 C17 C16 116.28(16) . . ?
F1 C3 C4 116.51(16) . . ?
C2 C3 F1 120.97(17) . . ?
C2 C3 C4 122.51(18) . . ?
O1 C1 N2 120.91(17) . . ?
O1 C1 N1 123.38(17) . . ?
N1 C1 N2 115.71(16) . . ?
N1 C2 H2A 119.5 . . ?
C3 C2 N1 121.09(17) . . ?
C3 C2 H2A 119.5 . . ?
C10 C9 C14 117.55(17) . . ?
C10 C9 H9A 121.2 . . ?
C14 C9 H9A 121.2 . . ?
C00J C18 H18 119.4 . . ?
C20 C18 C00J 121.28(17) . . ?
C20 C18 H18 119.4 . . ?
O3 C5 N1 108.26(15) . . ?
O3 C5 H5A 110.2 . . ?
O3 C5 C6 106.03(16) . . ?
N1 C5 H5A 110.2 . . ?
C6 C5 N1 111.88(16) . . ?
C6 C5 H5A 110.2 . . ?
C5 C6 H6A 111.3 . . ?
C5 C6 H6B 111.3 . . ?
C5 C6 C7 102.15(17) . . ?
H6A C6 H6B 109.2 . . ?
C7 C6 H6A 111.3 . . ?
C7 C6 H6B 111.3 . . ?
O3 C8 H8A 110.5 . . ?
O3 C8 H8B 110.5 . . ?
O3 C8 C7 106.11(17) . . ?
H8A C8 H8B 108.7 . . ?
C7 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
C6 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 C6 103.42(18) . . ?
C8 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.0 . . ?
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 C3 1.345(2) . ?
O6 C10 1.363(2) . ?
O6 C15 1.376(2) . ?
O10 H10 0.8200 . ?
O10 C22 1.373(2) . ?
O4 H4 0.8200 . ?
O4 C12 1.350(2) . ?
O9 H9 0.8200 . ?
O9 C20 1.359(2) . ?
O7 H7 0.8200 . ?
O7 C16 1.365(2) . ?
O5 H5 0.8200 . ?
O5 C14 1.358(2) . ?
O8 C17 1.255(2) . ?
O11 H11 0.8200 . ?
O11 C21 1.372(2) . ?
O2 C4 1.235(2) . ?
O1 C1 1.222(2) . ?
O3 C5 1.404(2) . ?
O3 C8 1.474(3) . ?
N2 H2 0.8600 . ?
N2 C4 1.375(3) . ?
N2 C1 1.385(2) . ?
N1 C1 1.369(2) . ?
N1 C2 1.377(3) . ?
N1 C5 1.513(2) . ?
C10 C11 1.400(3) . ?
C10 C9 1.385(3) . ?
C12 C11 1.416(3) . ?
C12 C13 1.381(3) . ?
C21 C22 1.399(3) . ?
C21 C19 1.379(3) . ?
C15 C00J 1.466(3) . ?
C15 C16 1.357(3) . ?
C00J C19 1.400(3) . ?
C00J C18 1.395(3) . ?
C11 C17 1.433(3) . ?
C14 C13 1.395(3) . ?
C14 C9 1.386(3) . ?
C22 C20 1.388(3) . ?
C16 C17 1.448(3) . ?
C20 C18 1.387(3) . ?
C19 H19 0.9300 . ?
C4 C3 1.434(3) . ?
C13 H13 0.9300 . ?
C3 C2 1.335(3) . ?
C2 H2A 0.9300 . ?
C9 H9A 0.9300 . ?
C18 H18 0.9300 . ?
C5 H5A 0.9800 . ?
C5 C6 1.513(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.527(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.510(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
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 C3 C2 N1 -179.17(16) . . . . ?
O6 C10 C11 C12 -179.55(15) . . . . ?
O6 C10 C11 C17 -1.8(3) . . . . ?
O6 C10 C9 C14 179.11(16) . . . . ?
O6 C15 C00J C19 -173.06(16) . . . . ?
O6 C15 C00J C18 7.1(2) . . . . ?
O6 C15 C16 O7 179.41(15) . . . . ?
O6 C15 C16 C17 -0.4(3) . . . . ?
O10 C22 C20 O9 2.2(3) . . . . ?
O10 C22 C20 C18 -179.76(16) . . . . ?
O4 C12 C11 C10 179.03(16) . . . . ?
O4 C12 C11 C17 1.4(3) . . . . ?
O4 C12 C13 C14 -177.86(17) . . . . ?
O9 C20 C18 C00J 179.35(16) . . . . ?
O7 C16 C17 O8 -0.1(3) . . . . ?
O7 C16 C17 C11 179.82(15) . . . . ?
O5 C14 C13 C12 177.87(17) . . . . ?
O5 C14 C9 C10 -178.56(16) . . . . ?
O11 C21 C22 O10 -1.8(3) . . . . ?
O11 C21 C22 C20 177.85(16) . . . . ?
O11 C21 C19 C00J -178.88(17) . . . . ?
O2 C4 C3 F1 -2.3(3) . . . . ?
O2 C4 C3 C2 179.23(19) . . . . ?
O3 C5 C6 C7 35.0(2) . . . . ?
O3 C8 C7 C6 20.2(2) . . . . ?
N2 C4 C3 F1 177.82(16) . . . . ?
N2 C4 C3 C2 -0.7(3) . . . . ?
N1 C5 C6 C7 -82.77(19) . . . . ?
C10 O6 C15 C00J -178.94(15) . . . . ?
C10 O6 C15 C16 0.1(3) . . . . ?
C10 C11 C17 O8 -178.59(17) . . . . ?
C10 C11 C17 C16 1.4(3) . . . . ?
C12 C11 C17 O8 -1.0(3) . . . . ?
C12 C11 C17 C16 179.06(16) . . . . ?
C21 C22 C20 O9 -177.54(17) . . . . ?
C21 C22 C20 C18 0.6(3) . . . . ?
C15 O6 C10 C11 1.1(3) . . . . ?
C15 O6 C10 C9 -177.83(15) . . . . ?
C15 C00J C19 C21 -178.20(17) . . . . ?
C15 C00J C18 C20 177.62(16) . . . . ?
C15 C16 C17 O8 179.69(17) . . . . ?
C15 C16 C17 C11 -0.4(3) . . . . ?
C00J C15 C16 O7 -1.8(3) . . . . ?
C00J C15 C16 C17 178.41(17) . . . . ?
C11 C10 C9 C14 0.2(3) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C22 C21 C19 C00J 0.0(3) . . . . ?
C22 C20 C18 C00J 1.1(3) . . . . ?
C16 C15 C00J C19 8.1(3) . . . . ?
C16 C15 C00J C18 -171.80(18) . . . . ?
C19 C21 C22 O10 179.19(17) . . . . ?
C19 C21 C22 C20 -1.1(3) . . . . ?
C19 C00J C18 C20 -2.2(3) . . . . ?
C4 N2 C1 O1 -176.93(17) . . . . ?
C4 N2 C1 N1 2.6(3) . . . . ?
C4 C3 C2 N1 -0.7(3) . . . . ?
C13 C12 C11 C10 0.0(3) . . . . ?
C13 C12 C11 C17 -177.65(16) . . . . ?
C13 C14 C9 C10 1.0(3) . . . . ?
C1 N2 C4 O2 179.77(17) . . . . ?
C1 N2 C4 C3 -0.3(3) . . . . ?
C1 N1 C2 C3 3.2(3) . . . . ?
C1 N1 C5 O3 174.73(16) . . . . ?
C1 N1 C5 C6 -68.8(2) . . . . ?
C2 N1 C1 O1 175.56(18) . . . . ?
C2 N1 C1 N2 -4.0(2) . . . . ?
C2 N1 C5 O3 -0.7(2) . . . . ?
C2 N1 C5 C6 115.8(2) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C9 C10 C11 C17 177.00(17) . . . . ?
C9 C14 C13 C12 -1.7(3) . . . . ?
C18 C00J C19 C21 1.6(3) . . . . ?
C5 O3 C8 C7 1.6(2) . . . . ?
C5 N1 C1 O1 0.1(3) . . . . ?
C5 N1 C1 N2 -179.41(16) . . . . ?
C5 N1 C2 C3 178.56(17) . . . . ?
C5 C6 C7 C8 -33.0(2) . . . . ?
C8 O3 C5 N1 96.96(18) . . . . ?
C8 O3 C5 C6 -23.2(2) . . . . ?
