#------------------------------------------------------------------------------
#$Date: 2020-03-26 04:31:33 +0200 (Thu, 26 Mar 2020) $
#$Revision: 249721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240200.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_7240200
loop_
_publ_author_name
'Pettersen, Anna'
'Putra, Okky Dwichandra'
'Light, Mark E.'
'Namatame, Yukiko'
_publ_section_title
;
 Invitation to Submit: The Cambridge Structural Database " A peculiar
 dehydration and solid-solid phase transition of the active pharmaceutical
 ingredient AZD9898 based on in situ single crystal-to-single crystal
 transformations "
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00276C
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C20 H19 Cl F3 N3 O4), 0.5(H2 O)'
_chemical_formula_sum            'C40 H39 Cl2 F6 N6 O8.5'
_chemical_formula_weight         924.66
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-02-07 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                103.378(3)
_cell_angle_beta                 105.493(3)
_cell_angle_gamma                104.407(3)
_cell_formula_units_Z            1
_cell_length_a                   9.0757(3)
_cell_length_b                   11.0502(4)
_cell_length_c                   11.7199(5)
_cell_measurement_reflns_used    10496
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.698
_cell_measurement_theta_min      3.109
_cell_volume                     1039.69(8)
_computing_cell_refinement
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_pressure         101.3
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25300
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         3.109
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rotating anode'
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       plate
_exptl_crystal_F_000             477
_exptl_crystal_recrystallization_method
'the material was recrystallized from --- by slow evaporation'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 3447 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         10496
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0429
_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)+(0.0596P)²+0.0049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                8772
_reflns_number_total             10496
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00276c2.cif
_cod_data_source_block           2016scas0001_R_100K
_cod_original_cell_volume        1039.68(7)
_cod_original_formula_sum        'C40 H39 Cl2 F6 N6 O8.50'
_cod_database_code               7240200
_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.
;
loop_
_space_group_symop_operation_xyz
'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
Cl11 Cl 0.40375(10) -0.40556(8) -0.01781(8) 0.0242(2) Uani 1 1 d . . . . .
F101 F 0.1243(3) -0.3763(2) 0.0489(2) 0.0253(5) Uani 1 1 d . . . . .
F102 F 0.2600(2) 0.08021(19) 0.12721(19) 0.0203(5) Uani 1 1 d . . . . .
F103 F 0.2422(2) 0.0272(2) -0.1406(2) 0.0230(5) Uani 1 1 d . . . . .
O101 O 0.8317(3) 0.5342(2) 0.2608(2) 0.0184(5) Uani 1 1 d . . . . .
O102 O 0.8521(3) 0.6218(2) 0.5098(2) 0.0300(6) Uani 1 1 d . . . . .
O103 O 0.9558(3) 0.3599(2) 0.8131(2) 0.0209(5) Uani 1 1 d D . . . .
O104 O 0.7302(3) 0.3862(3) 0.8426(2) 0.0328(6) Uani 1 1 d . . . . .
N101 N 0.5296(3) 0.0951(3) 0.0588(3) 0.0140(6) Uani 1 1 d . . . . .
N102 N 0.6858(3) 0.3152(3) 0.1604(3) 0.0135(6) Uani 1 1 d . . . . .
N103 N 0.7086(3) 0.2786(3) 0.3887(3) 0.0153(6) Uani 1 1 d . . . . .
C101 C 0.4664(4) -0.1427(3) 0.0268(3) 0.0141(7) Uani 1 1 d . . . . .
H101 H 0.560830 -0.141051 0.005735 0.017 Uiso 1 1 calc R U . . .
C102 C 0.3634(4) -0.2602(3) 0.0232(3) 0.0170(7) Uani 1 1 d . . . . .
C103 C 0.2254(4) -0.2615(3) 0.0535(3) 0.0187(8) Uani 1 1 d . . . . .
C104 C 0.1870(4) -0.1478(4) 0.0885(3) 0.0183(7) Uani 1 1 d . . . . .
H104 H 0.092164 -0.149661 0.108930 0.022 Uiso 1 1 calc R U . . .
C105 C 0.2923(4) -0.0322(3) 0.0924(3) 0.0152(7) Uani 1 1 d . . . . .
C106 C 0.4312(4) -0.0261(4) 0.0615(3) 0.0137(7) Uani 1 1 d . . . . .
C107 C 0.5289(4) 0.1063(3) -0.0641(3) 0.0152(7) Uani 1 1 d . . . . .
H10A H 0.539029 0.025061 -0.113545 0.018 Uiso 1 1 calc R U . . .
H10B H 0.624756 0.181060 -0.051784 0.018 Uiso 1 1 calc R U . . .
C108 C 0.3768(4) 0.1274(3) -0.1385(3) 0.0156(7) Uani 1 1 d . . . . .
C109 C 0.3683(5) 0.1046(4) -0.2732(4) 0.0248(8) Uani 1 1 d . . . . .
H10C H 0.365920 0.014495 -0.309371 0.037 Uiso 1 1 calc R U . . .
H10D H 0.463557 0.167508 -0.276132 0.037 Uiso 1 1 calc R U . . .
H10E H 0.269834 0.116980 -0.321039 0.037 Uiso 1 1 calc R U . . .
C110 C 0.3603(4) 0.2586(4) -0.0799(4) 0.0200(8) Uani 1 1 d . . . . .
H11A H 0.262136 0.266858 -0.133045 0.030 Uiso 1 1 calc R U . . .
H11B H 0.455170 0.330483 -0.071501 0.030 Uiso 1 1 calc R U . . .
H11C H 0.352885 0.263286 0.002853 0.030 Uiso 1 1 calc R U . . .
C111 C 0.6141(4) 0.1973(3) 0.1672(3) 0.0130(6) Uani 1 1 d . . . . .
C112 C 0.7612(4) 0.4150(4) 0.2653(3) 0.0153(7) Uani 1 1 d . . . . .
C113 C 0.7732(4) 0.3992(3) 0.3832(3) 0.0158(7) Uani 1 1 d . . . . .
C114 C 0.6278(4) 0.1783(3) 0.2842(3) 0.0159(7) Uani 1 1 d . . . . .
H114 H 0.578756 0.093371 0.287994 0.019 Uiso 1 1 calc R U . . .
C115 C 0.8158(4) 0.5459(4) 0.1382(4) 0.0223(8) Uani 1 1 d . . . . .
H11D H 0.700827 0.521302 0.088962 0.033 Uiso 1 1 calc R U . . .
H11E H 0.863755 0.487214 0.096096 0.033 Uiso 1 1 calc R U . . .
H11F H 0.872112 0.637190 0.146347 0.033 Uiso 1 1 calc R U . . .
C116 C 0.8473(4) 0.5095(4) 0.5041(3) 0.0205(8) Uani 1 1 d . . . . .
C117 C 0.9165(4) 0.4737(3) 0.6180(3) 0.0174(6) Uani 1 1 d . . . . .
H117 H 0.951350 0.394080 0.604850 0.021 Uiso 1 1 calc R U . . .
C118 C 0.8485(4) 0.5028(3) 0.7247(3) 0.0218(7) Uani 1 1 d . . . . .
H118 H 0.761648 0.544104 0.711104 0.026 Uiso 1 1 calc R U . . .
C119 C 1.0152(4) 0.5861(3) 0.7360(3) 0.0258(7) Uani 1 1 d . . . . .
H11G H 1.029324 0.676658 0.731997 0.031 Uiso 1 1 calc R U . . .
H11H H 1.110353 0.576321 0.793394 0.031 Uiso 1 1 calc R U . . .
C120 C 0.8372(4) 0.4108(4) 0.7990(3) 0.0232(7) Uani 1 1 d . . . . .
Cl12 Cl 0.30451(10) 0.91878(8) 0.41109(8) 0.0226(2) Uani 1 1 d . . . . .
F201 F 0.5890(2) 0.8899(2) 0.3517(2) 0.0239(5) Uani 1 1 d . . . . .
F202 F 0.4457(2) 0.4319(2) 0.2653(2) 0.0222(5) Uani 1 1 d . . . . .
F203 F 0.4561(2) 0.4874(2) 0.5362(2) 0.0265(5) Uani 1 1 d . . . . .
O201 O -0.1344(3) -0.0214(2) 0.1286(2) 0.0205(6) Uani 1 1 d . . . . .
O202 O -0.2646(3) -0.0987(2) -0.1274(2) 0.0242(5) Uani 1 1 d . . . . .
N201 N 0.1709(3) 0.4174(3) 0.3268(3) 0.0141(6) Uani 1 1 d . . . . .
N202 N 0.0141(3) 0.1977(3) 0.2265(3) 0.0159(6) Uani 1 1 d . . . . .
N203 N -0.0041(3) 0.2307(3) -0.0035(3) 0.0163(6) Uani 1 1 d . . . . .
C201 C 0.2372(4) 0.6545(4) 0.3611(3) 0.0161(7) Uani 1 1 d . . . . .
H201 H 0.140831 0.652601 0.379186 0.019 Uiso 1 1 calc R U . . .
C202 C 0.3444(4) 0.7728(3) 0.3686(3) 0.0157(7) Uani 1 1 d . . . . .
C203 C 0.4851(4) 0.7745(3) 0.3436(3) 0.0170(7) Uani 1 1 d . . . . .
C204 C 0.5232(4) 0.6617(4) 0.3094(3) 0.0177(7) Uani 1 1 d . . . . .
H204 H 0.620447 0.663769 0.292659 0.021 Uiso 1 1 calc R U . . .
C205 C 0.4127(4) 0.5449(3) 0.3005(3) 0.0168(7) Uani 1 1 d . . . . .
C206 C 0.2729(4) 0.5388(3) 0.3266(3) 0.0144(7) Uani 1 1 d . . . . .
C207 C 0.1698(4) 0.4065(3) 0.4489(3) 0.0158(7) Uani 1 1 d . . . . .
H20A H 0.072513 0.332631 0.435776 0.019 Uiso 1 1 calc R U . . .
H20B H 0.159974 0.488303 0.497637 0.019 Uiso 1 1 calc R U . . .
C208 C 0.3191(4) 0.3840(4) 0.5261(4) 0.0191(7) Uani 1 1 d . . . . .
C209 C 0.3169(5) 0.4011(4) 0.6579(4) 0.0243(8) Uani 1 1 d . . . . .
H20C H 0.415882 0.392512 0.709517 0.036 Uiso 1 1 calc R U . . .
H20D H 0.222164 0.333318 0.655718 0.036 Uiso 1 1 calc R U . . .
H20E H 0.311338 0.488600 0.693546 0.036 Uiso 1 1 calc R U . . .
C210 C 0.3389(5) 0.2560(4) 0.4659(4) 0.0244(8) Uani 1 1 d . . . . .
H21A H 0.336077 0.250170 0.380550 0.037 Uiso 1 1 calc R U . . .
H21B H 0.250628 0.182206 0.463491 0.037 Uiso 1 1 calc R U . . .
H21C H 0.443012 0.252284 0.514380 0.037 Uiso 1 1 calc R U . . .
C211 C 0.0875(4) 0.3143(3) 0.2180(3) 0.0147(7) Uani 1 1 d . . . . .
C212 C -0.0650(4) 0.0988(3) 0.1207(3) 0.0144(7) Uani 1 1 d . . . . .
C213 C -0.0763(4) 0.1114(4) 0.0022(3) 0.0170(7) Uani 1 1 d . . . . .
C214 C 0.0767(4) 0.3313(3) 0.1003(3) 0.0158(7) Uani 1 1 d . . . . .
H214 H 0.127724 0.415497 0.095917 0.019 Uiso 1 1 calc R U . . .
C215 C -0.1089(5) -0.0325(4) 0.2520(4) 0.0238(8) Uani 1 1 d . . . . .
H21D H -0.172551 -0.121076 0.245687 0.036 Uiso 1 1 calc R U . . .
H21E H -0.143051 0.033072 0.300608 0.036 Uiso 1 1 calc R U . . .
H21F H 0.006371 -0.016876 0.293641 0.036 Uiso 1 1 calc R U . . .
C216 C -0.1599(4) 0.0013(4) -0.1172(3) 0.0178(7) Uani 1 1 d . . . . .
O203 O -0.3180(3) 0.1590(2) -0.4367(2) 0.0182(5) Uani 1 1 d D . . . .
O204 O -0.0846(3) 0.1249(3) -0.4381(2) 0.0252(5) Uani 1 1 d . . . . .
C217 C -0.1118(4) 0.0202(3) -0.2261(3) 0.0205(6) Uani 1 1 d . . . . .
H217 H -0.003724 0.086837 -0.206719 0.025 Uiso 1 1 calc R U . . .
C218 C -0.2479(4) 0.0083(3) -0.3422(3) 0.0203(6) Uani 1 1 d . . . . .
H218 H -0.360040 -0.014268 -0.338797 0.024 Uiso 1 1 calc R U . . .
C219 C -0.1694(5) -0.0955(3) -0.3409(3) 0.0290(8) Uani 1 1 d . . . . .
H21G H -0.233286 -0.181324 -0.338913 0.035 Uiso 1 1 calc R U . . .
H21H H -0.096935 -0.101248 -0.390398 0.035 Uiso 1 1 calc R U . . .
C220 C -0.2057(4) 0.1020(3) -0.4109(3) 0.0186(6) Uani 1 1 d . . . . .
H203 H -0.290(5) 0.205(4) -0.480(4) 0.028 Uiso 1 1 d D U . . .
H103 H 0.943(5) 0.316(4) 0.860(4) 0.028 Uiso 1 1 d D U . . .
O1W O 0.7869(14) 0.7012(12) 0.9718(13) 0.110(4) Uani 0.5 1 d G . P . .
H1WA H 0.751671 0.765998 0.977736 0.165 Uiso 0.5 1 d G U P . .
H1WB H 0.707416 0.629545 0.941246 0.165 Uiso 0.5 1 d G U P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C112 O101 C115 116.7(3) . . ?
C120 O103 H103 106(3) . . ?
C111 N101 C106 119.9(3) . . ?
C111 N101 C107 122.5(3) . . ?
C106 N101 C107 117.6(3) . . ?
C112 N102 C111 118.2(3) . . ?
C114 N103 C113 119.9(3) . . ?
C102 C101 C106 119.8(3) . . ?
C102 C101 H101 120.1 . . ?
C106 C101 H101 120.1 . . ?
C101 C102 C103 119.6(3) . . ?
C101 C102 Cl11 121.1(3) . . ?
C103 C102 Cl11 119.3(3) . . ?
F101 C103 C104 118.4(3) . . ?
F101 C103 C102 119.5(3) . . ?
C104 C103 C102 122.1(3) . . ?
C105 C104 C103 117.1(3) . . ?
C105 C104 H104 121.5 . . ?
C103 C104 H104 121.5 . . ?
F102 C105 C104 118.7(3) . . ?
F102 C105 C106 118.3(3) . . ?
C104 C105 C106 123.0(3) . . ?
C105 C106 C101 118.4(3) . . ?
C105 C106 N101 120.4(3) . . ?
C101 C106 N101 121.0(3) . . ?
N101 C107 C108 113.8(3) . . ?
N101 C107 H10A 108.8 . . ?
C108 C107 H10A 108.8 . . ?
N101 C107 H10B 108.8 . . ?
C108 C107 H10B 108.8 . . ?
H10A C107 H10B 107.7 . . ?
F103 C108 C110 107.0(3) . . ?
F103 C108 C109 106.3(3) . . ?
C110 C108 C109 113.0(3) . . ?
F103 C108 C107 106.8(3) . . ?
C110 C108 C107 113.6(3) . . ?
C109 C108 C107 109.6(3) . . ?
C108 C109 H10C 109.5 . . ?
C108 C109 H10D 109.5 . . ?
H10C C109 H10D 109.5 . . ?
C108 C109 H10E 109.5 . . ?
H10C C109 H10E 109.5 . . ?
H10D C109 H10E 109.5 . . ?
C108 C110 H11A 109.5 . . ?
C108 C110 H11B 109.5 . . ?
H11A C110 H11B 109.5 . . ?
C108 C110 H11C 109.5 . . ?
H11A C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?
N102 C111 N101 118.6(3) . . ?
N102 C111 C114 120.7(3) . . ?
N101 C111 C114 120.7(3) . . ?
N102 C112 O101 119.4(3) . . ?
N102 C112 C113 122.1(3) . . ?
O101 C112 C113 118.5(3) . . ?
N103 C113 C112 118.8(3) . . ?
N103 C113 C116 116.7(3) . . ?
C112 C113 C116 124.5(3) . . ?
N103 C114 C111 120.1(3) . . ?
N103 C114 H114 119.9 . . ?
C111 C114 H114 119.9 . . ?
O101 C115 H11D 109.5 . . ?
O101 C115 H11E 109.5 . . ?
H11D C115 H11E 109.5 . . ?
O101 C115 H11F 109.5 . . ?
H11D C115 H11F 109.5 . . ?
H11E C115 H11F 109.5 . . ?
O102 C116 C113 122.0(3) . . ?
O102 C116 C117 122.0(3) . . ?
C113 C116 C117 116.0(3) . . ?
C119 C117 C116 116.4(3) . . ?
C119 C117 C118 59.8(2) . . ?
C116 C117 C118 117.6(3) . . ?
C119 C117 H117 116.9 . . ?
C116 C117 H117 116.9 . . ?
C118 C117 H117 116.9 . . ?
C120 C118 C119 118.4(3) . . ?
C120 C118 C117 118.3(3) . . ?
C119 C118 C117 58.7(2) . . ?
C120 C118 H118 116.4 . . ?
C119 C118 H118 116.4 . . ?
C117 C118 H118 116.4 . . ?
C117 C119 C118 61.4(2) . . ?
C117 C119 H11G 117.6 . . ?
C118 C119 H11G 117.6 . . ?
C117 C119 H11H 117.6 . . ?
C118 C119 H11H 117.6 . . ?
H11G C119 H11H 114.7 . . ?
O104 C120 O103 123.9(3) . . ?
O104 C120 C118 123.0(3) . . ?
O103 C120 C118 113.0(3) . . ?
C212 O201 C215 117.1(3) . . ?
C211 N201 C206 120.7(3) . . ?
C211 N201 C207 122.4(3) . . ?
C206 N201 C207 116.7(3) . . ?
C212 N202 C211 117.1(3) . . ?
C214 N203 C213 120.1(3) . . ?
C202 C201 C206 119.1(3) . . ?
C202 C201 H201 120.4 . . ?
C206 C201 H201 120.4 . . ?
C203 C202 C201 119.9(3) . . ?
C203 C202 Cl12 119.6(3) . . ?
C201 C202 Cl12 120.5(2) . . ?
F201 C203 C204 118.4(3) . . ?
F201 C203 C202 119.5(3) . . ?
C204 C203 C202 122.2(3) . . ?
C203 C204 C205 116.7(3) . . ?
C203 C204 H204 121.6 . . ?
C205 C204 H204 121.6 . . ?
F202 C205 C206 118.8(3) . . ?
F202 C205 C204 118.1(3) . . ?
C206 C205 C204 123.1(3) . . ?
C205 C206 C201 119.0(3) . . ?
C205 C206 N201 120.6(3) . . ?
C201 C206 N201 120.3(3) . . ?
N201 C207 C208 114.9(3) . . ?
N201 C207 H20A 108.5 . . ?
C208 C207 H20A 108.5 . . ?
N201 C207 H20B 108.5 . . ?
C208 C207 H20B 108.5 . . ?
H20A C207 H20B 107.5 . . ?
F203 C208 C210 107.3(3) . . ?
F203 C208 C209 106.2(3) . . ?
C210 C208 C209 113.7(3) . . ?
F203 C208 C207 106.7(3) . . ?
C210 C208 C207 113.4(3) . . ?
C209 C208 C207 108.9(3) . . ?
C208 C209 H20C 109.5 . . ?
C208 C209 H20D 109.5 . . ?
H20C C209 H20D 109.5 . . ?
C208 C209 H20E 109.5 . . ?
H20C C209 H20E 109.5 . . ?
H20D C209 H20E 109.5 . . ?
C208 C210 H21A 109.5 . . ?
C208 C210 H21B 109.5 . . ?
H21A C210 H21B 109.5 . . ?
C208 C210 H21C 109.5 . . ?
H21A C210 H21C 109.5 . . ?
H21B C210 H21C 109.5 . . ?
N202 C211 N201 117.8(3) . . ?
N202 C211 C214 121.0(3) . . ?
N201 C211 C214 121.2(3) . . ?
N202 C212 O201 117.6(3) . . ?
N202 C212 C213 123.5(3) . . ?
O201 C212 C213 118.9(3) . . ?
N203 C213 C212 118.0(3) . . ?
N203 C213 C216 117.5(3) . . ?
C212 C213 C216 124.4(3) . . ?
N203 C214 C211 120.3(3) . . ?
N203 C214 H214 119.8 . . ?
C211 C214 H214 119.8 . . ?
O201 C215 H21D 109.5 . . ?
O201 C215 H21E 109.5 . . ?
H21D C215 H21E 109.5 . . ?
O201 C215 H21F 109.5 . . ?
H21D C215 H21F 109.5 . . ?
H21E C215 H21F 109.5 . . ?
O202 C216 C213 122.3(3) . . ?
O202 C216 C217 121.4(3) . . ?
C213 C216 C217 116.3(3) . . ?
C220 O203 H203 106(3) . . ?
C219 C217 C216 118.3(3) . . ?
C219 C217 C218 59.4(2) . . ?
C216 C217 C218 116.3(3) . . ?
C219 C217 H217 116.8 . . ?
C216 C217 H217 116.8 . . ?
C218 C217 H217 116.8 . . ?
C220 C218 C219 118.6(3) . . ?
C220 C218 C217 115.8(3) . . ?
C219 C218 C217 59.0(2) . . ?
C220 C218 H218 116.9 . . ?
C219 C218 H218 116.9 . . ?
C217 C218 H218 116.9 . . ?
C217 C219 C218 61.6(2) . . ?
C217 C219 H21G 117.6 . . ?
C218 C219 H21G 117.6 . . ?
C217 C219 H21H 117.6 . . ?
C218 C219 H21H 117.6 . . ?
H21G C219 H21H 114.7 . . ?
O204 C220 O203 124.3(3) . . ?
O204 C220 C218 124.7(3) . . ?
O203 C220 C218 111.0(3) . . ?
H1WA O1W H1WB 109.5 . . ?
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
Cl11 C102 1.725(3) . ?
F101 C103 1.348(4) . ?
F102 C105 1.344(4) . ?
F103 C108 1.420(4) . ?
O101 C112 1.333(4) . ?
O101 C115 1.445(4) . ?
O102 C116 1.216(4) . ?
O103 C120 1.324(4) . ?
O103 H103 0.82(2) . ?
O104 C120 1.215(4) . ?
N101 C111 1.365(4) . ?
N101 C106 1.425(4) . ?
N101 C107 1.472(4) . ?
N102 C112 1.321(4) . ?
N102 C111 1.333(4) . ?
N103 C114 1.324(4) . ?
N103 C113 1.340(4) . ?
C101 C102 1.383(5) . ?
C101 C106 1.400(5) . ?
C101 H101 0.9500 . ?
C102 C103 1.388(5) . ?
C103 C104 1.387(5) . ?
C104 C105 1.374(5) . ?
C104 H104 0.9500 . ?
C105 C106 1.391(5) . ?
C107 C108 1.526(5) . ?
C107 H10A 0.9900 . ?
C107 H10B 0.9900 . ?
C108 C110 1.516(5) . ?
C108 C109 1.517(5) . ?
C109 H10C 0.9800 . ?
C109 H10D 0.9800 . ?
C109 H10E 0.9800 . ?
C110 H11A 0.9800 . ?
C110 H11B 0.9800 . ?
C110 H11C 0.9800 . ?
C111 C114 1.413(5) . ?
C112 C113 1.411(5) . ?
C113 C116 1.493(5) . ?
C114 H114 0.9500 . ?
C115 H11D 0.9800 . ?
C115 H11E 0.9800 . ?
C115 H11F 0.9800 . ?
C116 C117 1.501(5) . ?
C117 C119 1.499(4) . ?
C117 C118 1.540(4) . ?
C117 H117 1.0000 . ?
C118 C120 1.486(5) . ?
C118 C119 1.516(5) . ?
C118 H118 1.0000 . ?
C119 H11G 0.9900 . ?
C119 H11H 0.9900 . ?
Cl12 C202 1.731(3) . ?
F201 C203 1.350(4) . ?
F202 C205 1.354(4) . ?
F203 C208 1.420(4) . ?
O201 C212 1.357(4) . ?
O201 C215 1.441(5) . ?
O202 C216 1.222(4) . ?
N201 C211 1.370(5) . ?
N201 C206 1.429(4) . ?
N201 C207 1.466(4) . ?
N202 C212 1.324(5) . ?
N202 C211 1.335(4) . ?
N203 C214 1.321(5) . ?
N203 C213 1.344(5) . ?
C201 C202 1.390(5) . ?
C201 C206 1.393(5) . ?
C201 H201 0.9500 . ?
C202 C203 1.381(5) . ?
C203 C204 1.375(5) . ?
C204 C205 1.386(5) . ?
C204 H204 0.9500 . ?
C205 C206 1.372(5) . ?
C207 C208 1.528(5) . ?
C207 H20A 0.9900 . ?
C207 H20B 0.9900 . ?
C208 C210 1.504(5) . ?
C208 C209 1.519(5) . ?
C209 H20C 0.9800 . ?
C209 H20D 0.9800 . ?
C209 H20E 0.9800 . ?
C210 H21A 0.9800 . ?
C210 H21B 0.9800 . ?
C210 H21C 0.9800 . ?
C211 C214 1.416(5) . ?
C212 C213 1.407(5) . ?
C213 C216 1.483(5) . ?
C214 H214 0.9500 . ?
C215 H21D 0.9800 . ?
C215 H21E 0.9800 . ?
C215 H21F 0.9800 . ?
C216 C217 1.497(5) . ?
O203 C220 1.330(4) . ?
O203 H203 0.84(2) . ?
O204 C220 1.208(4) . ?
C217 C219 1.488(4) . ?
C217 C218 1.527(4) . ?
C217 H217 1.0000 . ?
C218 C220 1.490(5) . ?
C218 C219 1.494(4) . ?
C218 H218 1.0000 . ?
C219 H21G 0.9900 . ?
C219 H21H 0.9900 . ?
O1W H1WA 0.8497 . ?
O1W H1WB 0.8500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O103 H103 N203 0.82(2) 2.05(3) 2.837(4) 161(4) 1_656
O203 H203 N103 0.84(2) 1.90(3) 2.711(4) 162(4) 1_454
O1W H1WA O202 0.85 2.15 2.806(12) 133.3 1_666
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
C106 C101 C102 C103 0.4(5) . . . . ?
C106 C101 C102 Cl11 -179.4(3) . . . . ?
C101 C102 C103 F101 179.4(3) . . . . ?
Cl11 C102 C103 F101 -0.8(5) . . . . ?
C101 C102 C103 C104 -0.5(5) . . . . ?
Cl11 C102 C103 C104 179.3(3) . . . . ?
F101 C103 C104 C105 180.0(3) . . . . ?
C102 C103 C104 C105 -0.1(5) . . . . ?
C103 C104 C105 F102 -179.3(3) . . . . ?
C103 C104 C105 C106 0.8(5) . . . . ?
F102 C105 C106 C101 179.2(3) . . . . ?
C104 C105 C106 C101 -1.0(5) . . . . ?
F102 C105 C106 N101 -4.3(5) . . . . ?
C104 C105 C106 N101 175.5(3) . . . . ?
C102 C101 C106 C105 0.3(5) . . . . ?
C102 C101 C106 N101 -176.2(3) . . . . ?
C111 N101 C106 C105 67.6(4) . . . . ?
C107 N101 C106 C105 -109.3(4) . . . . ?
C111 N101 C106 C101 -116.0(4) . . . . ?
C107 N101 C106 C101 67.1(4) . . . . ?
C111 N101 C107 C108 -100.8(3) . . . . ?
C106 N101 C107 C108 76.1(4) . . . . ?
N101 C107 C108 F103 -51.5(4) . . . . ?
N101 C107 C108 C110 66.2(4) . . . . ?
N101 C107 C108 C109 -166.3(3) . . . . ?
C112 N102 C111 N101 177.1(3) . . . . ?
C112 N102 C111 C114 -4.0(4) . . . . ?
C106 N101 C111 N102 -170.2(3) . . . . ?
C107 N101 C111 N102 6.6(4) . . . . ?
C106 N101 C111 C114 10.8(4) . . . . ?
C107 N101 C111 C114 -172.4(3) . . . . ?
C111 N102 C112 O101 -179.0(3) . . . . ?
C111 N102 C112 C113 2.5(4) . . . . ?
C115 O101 C112 N102 1.7(4) . . . . ?
C115 O101 C112 C113 -179.8(3) . . . . ?
C114 N103 C113 C112 -3.6(5) . . . . ?
C114 N103 C113 C116 173.7(3) . . . . ?
N102 C112 C113 N103 1.3(5) . . . . ?
O101 C112 C113 N103 -177.2(3) . . . . ?
N102 C112 C113 C116 -175.8(3) . . . . ?
O101 C112 C113 C116 5.7(5) . . . . ?
C113 N103 C114 C111 2.1(5) . . . . ?
N102 C111 C114 N103 1.8(5) . . . . ?
N101 C111 C114 N103 -179.3(3) . . . . ?
N103 C113 C116 O102 -151.0(3) . . . . ?
C112 C113 C116 O102 26.2(5) . . . . ?
N103 C113 C116 C117 29.4(4) . . . . ?
C112 C113 C116 C117 -153.4(3) . . . . ?
O102 C116 C117 C119 -9.6(5) . . . . ?
C113 C116 C117 C119 170.1(3) . . . . ?
O102 C116 C117 C118 58.5(5) . . . . ?
C113 C116 C117 C118 -121.8(3) . . . . ?
C119 C117 C118 C120 -107.8(3) . . . . ?
C116 C117 C118 C120 146.0(3) . . . . ?
C116 C117 C118 C119 -106.1(3) . . . . ?
C116 C117 C119 C118 108.0(3) . . . . ?
C120 C118 C119 C117 107.5(3) . . . . ?
C119 C118 C120 O104 145.7(3) . . . . ?
C117 C118 C120 O104 -146.5(3) . . . . ?
C119 C118 C120 O103 -33.8(4) . . . . ?
C117 C118 C120 O103 34.0(4) . . . . ?
C206 C201 C202 C203 -0.8(5) . . . . ?
C206 C201 C202 Cl12 180.0(3) . . . . ?
C201 C202 C203 F201 -179.6(3) . . . . ?
Cl12 C202 C203 F201 -0.4(5) . . . . ?
C201 C202 C203 C204 0.8(5) . . . . ?
Cl12 C202 C203 C204 -180.0(3) . . . . ?
F201 C203 C204 C205 -179.3(3) . . . . ?
C202 C203 C204 C205 0.3(5) . . . . ?
C203 C204 C205 F202 179.1(3) . . . . ?
C203 C204 C205 C206 -1.4(5) . . . . ?
F202 C205 C206 C201 -179.1(3) . . . . ?
C204 C205 C206 C201 1.4(6) . . . . ?
F202 C205 C206 N201 5.2(5) . . . . ?
C204 C205 C206 N201 -174.3(3) . . . . ?
C202 C201 C206 C205 -0.3(5) . . . . ?
C202 C201 C206 N201 175.5(3) . . . . ?
C211 N201 C206 C205 -67.9(4) . . . . ?
C207 N201 C206 C205 107.9(4) . . . . ?
C211 N201 C206 C201 116.4(4) . . . . ?
C207 N201 C206 C201 -67.8(4) . . . . ?
C211 N201 C207 C208 99.9(3) . . . . ?
C206 N201 C207 C208 -75.9(4) . . . . ?
N201 C207 C208 F203 54.9(4) . . . . ?
N201 C207 C208 C210 -63.1(4) . . . . ?
N201 C207 C208 C209 169.2(3) . . . . ?
C212 N202 C211 N201 -179.5(3) . . . . ?
C212 N202 C211 C214 1.7(4) . . . . ?
C206 N201 C211 N202 170.1(3) . . . . ?
C207 N201 C211 N202 -5.5(4) . . . . ?
C206 N201 C211 C214 -11.1(4) . . . . ?
C207 N201 C211 C214 173.3(3) . . . . ?
C211 N202 C212 O201 177.3(3) . . . . ?
C211 N202 C212 C213 -0.7(4) . . . . ?
C215 O201 C212 N202 -3.1(4) . . . . ?
C215 O201 C212 C213 175.0(3) . . . . ?
C214 N203 C213 C212 1.1(4) . . . . ?
C214 N203 C213 C216 -177.8(3) . . . . ?
N202 C212 C213 N203 -0.7(5) . . . . ?
O201 C212 C213 N203 -178.7(3) . . . . ?
N202 C212 C213 C216 178.1(3) . . . . ?
O201 C212 C213 C216 0.1(5) . . . . ?
C213 N203 C214 C211 -0.1(4) . . . . ?
N202 C211 C214 N203 -1.3(5) . . . . ?
N201 C211 C214 N203 179.9(3) . . . . ?
N203 C213 C216 O202 -159.1(3) . . . . ?
C212 C213 C216 O202 22.1(5) . . . . ?
N203 C213 C216 C217 19.6(4) . . . . ?
C212 C213 C216 C217 -159.2(3) . . . . ?
O202 C216 C217 C219 -12.1(5) . . . . ?
C213 C216 C217 C219 169.2(3) . . . . ?
O202 C216 C217 C218 55.6(4) . . . . ?
C213 C216 C217 C218 -123.1(3) . . . . ?
C219 C217 C218 C220 -109.3(3) . . . . ?
C216 C217 C218 C220 142.0(3) . . . . ?
C216 C217 C218 C219 -108.7(3) . . . . ?
C216 C217 C219 C218 105.5(3) . . . . ?
C220 C218 C219 C217 104.6(3) . . . . ?
C219 C218 C220 O204 -20.5(5) . . . . ?
C217 C218 C220 O204 46.7(4) . . . . ?
C219 C218 C220 O203 160.5(3) . . . . ?
C217 C218 C220 O203 -132.3(3) . . . . ?
