#------------------------------------------------------------------------------
#$Date: 2020-03-26 04:31:33 +0200 (Thu, 26 Mar 2020) $
#$Revision: 249721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240202.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_7240202
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         'C20 H19 Cl F3 N3 O4'
_chemical_formula_sum            'C20 H19 Cl F3 N3 O4'
_chemical_formula_weight         457.83
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-02-19
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.16 svn.r3264 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-02-07 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                107.504(4)
_cell_angle_beta                 100.890(5)
_cell_angle_gamma                104.746(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4219(6)
_cell_length_b                   11.2659(6)
_cell_length_c                   11.5862(6)
_cell_measurement_reflns_used    5840
_cell_measurement_temperature    410(2)
_cell_measurement_theta_max      28.6190
_cell_measurement_theta_min      2.2750
_cell_volume                     1086.25(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      410(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  71.00   1.00   10.00    --  -19.00  72.00 120.00  129
  2  ω    -58.00  71.00   1.00   10.00    --  -19.00  72.00 -90.00  129
  3  ω    -94.00  20.00   1.00   10.00    --  -19.00 -72.00-180.00  114
  4  ω    -69.00  20.00   1.00   10.00    --  -19.00 -72.00   0.00   89
  5  ω    -58.00  60.00   1.00   10.00    --  -19.00  72.00   0.00  118
  6  ω    -44.00  24.00   1.00   10.00    --  -19.00   0.00 150.00   68
  7  ω    -87.00  15.00   1.00   10.00    --  -19.00   0.00 -30.00  102
  8  ω    -48.00   4.00   1.00   10.00    --  -19.00  72.00-180.00   52
  9  ω    -15.00   4.00   1.00   10.00    --  -19.00 -72.00  60.00   19
 10  ω     -2.00  20.00   1.00   10.00    --  -19.00 -72.00-150.00   22
 11  ω    -58.00 -47.00   1.00   10.00    --  -19.00  72.00-150.00   11
 12  ω    -44.00 -34.00   1.00   10.00    --  -19.00  72.00  60.00   10
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0585375000
_diffrn_orient_matrix_UB_12      -0.0021013000
_diffrn_orient_matrix_UB_13      0.0470867000
_diffrn_orient_matrix_UB_21      -0.0324374000
_diffrn_orient_matrix_UB_22      0.0286697000
_diffrn_orient_matrix_UB_23      0.0471287000
_diffrn_orient_matrix_UB_31      -0.0461374000
_diffrn_orient_matrix_UB_32      -0.0638233000
_diffrn_orient_matrix_UB_33      -0.0073856000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22314
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         3.134
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'The material was recrystallised 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         0.229
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     566
_refine_ls_number_reflns         11088
_refine_ls_number_restraints     483
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.0692
_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)+(0.0841P)²+0.0097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.2004
_reflns_Friedel_coverage         0.981
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                4808
_reflns_number_total             11088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00276c2.cif
_cod_data_source_block           2016scas0001_r_410k
_cod_original_cell_volume        1086.25(11)
_cod_database_code               7240202
_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.
;
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 90.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.80
_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) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C117(H117), C118(H118), C217(H217), C218(H218)
3.b Secondary CH2 refined with riding coordinates:
 C107(H10A,H10B), C119(H11G,H11H), C207(H20A,H20B), C219(H21G,H21H)
3.c Me refined with riding coordinates:
 C115(H11D,H11E,H11F)
3.d Aromatic/amide H refined with riding coordinates:
 C101(H101), C104(H104), C114(H114), C201(H201), C204(H204), C214(H214)
3.e Idealised Me refined as rotating group:
 C109(H10C,H10D,H10E), C110(H11A,H11B,H11C), C209(H20C,H20D,H20E), C210(H21D,
 H21E,H21F), C215(H21A,H21B,H21C)
3.f Idealised tetrahedral OH refined as rotating group:
 O103(H103), O203(H203)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with superglue'
_olex2_submission_original_sample_id 'AZ13762986 Type 11, E15-013371-F '
_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 5.491
_oxdiff_exptl_absorpt_empirical_full_min 0.394
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 0.4004(4) -0.4010(2) -0.0067(2) 0.1210(9) Uani 1 1 d . U . . .
F101 F 0.1286(6) -0.3624(5) 0.0562(5) 0.1218(18) Uani 1 1 d . U . . .
F102 F 0.2672(5) 0.0862(5) 0.1331(5) 0.1004(14) Uani 1 1 d . U . . .
F103 F 0.2880(6) 0.0256(6) -0.1454(5) 0.132(2) Uani 1 1 d . U . . .
O101 O 0.8261(6) 0.5319(5) 0.2797(5) 0.0835(15) Uani 1 1 d . U . . .
O102 O 0.9133(9) 0.6234(6) 0.5333(6) 0.125(3) Uani 1 1 d . U . . .
O103 O 0.7410(11) 0.7012(6) 0.9220(7) 0.150(3) Uani 1 1 d . U . . .
H103 H 0.8043 0.7666 0.9222 0.224 Uiso 1 1 calc GR . . . .
O104 O 0.7019(10) 0.4894(6) 0.8602(6) 0.153(3) Uani 1 1 d . U . . .
N101 N 0.5364(6) 0.0948(5) 0.0702(5) 0.0619(14) Uani 1 1 d . U . . .
N102 N 0.6848(6) 0.3124(5) 0.1762(5) 0.0576(13) Uani 1 1 d . U . . .
N103 N 0.6881(6) 0.2877(5) 0.4050(5) 0.0592(13) Uani 1 1 d . U . . .
C101 C 0.4635(9) -0.1420(7) 0.0342(6) 0.0670(17) Uani 1 1 d . U . . .
H101 H 0.5537 -0.1443 0.0135 0.080 Uiso 1 1 calc R . . . .
C102 C 0.3593(10) -0.2568(7) 0.0307(6) 0.0761(19) Uani 1 1 d . U . . .
C103 C 0.2268(10) -0.2496(8) 0.0602(7) 0.083(2) Uani 1 1 d . U . . .
C104 C 0.1957(9) -0.1374(9) 0.0919(7) 0.084(2) Uani 1 1 d . U . . .
H104 H 0.1038 -0.1354 0.1094 0.101 Uiso 1 1 calc R . . . .
C105 C 0.3001(9) -0.0260(8) 0.0983(7) 0.0743(19) Uani 1 1 d . U . . .
C106 C 0.4326(8) -0.0237(6) 0.0688(6) 0.0581(15) Uani 1 1 d . U . . .
C107 C 0.5515(9) 0.1022(8) -0.0515(6) 0.076(2) Uani 1 1 d . U . . .
H10A H 0.5588 0.0194 -0.1026 0.092 Uiso 1 1 calc R . . . .
H10B H 0.6466 0.1712 -0.0361 0.092 Uiso 1 1 calc R . . . .
C108 C 0.4211(10) 0.1295(9) -0.1267(7) 0.086(2) Uani 1 1 d . U . . .
C109 C 0.4402(15) 0.1203(13) -0.2550(9) 0.142(4) Uani 1 1 d . U . . .
H10C H 0.4366 0.0325 -0.3009 0.213 Uiso 1 1 calc GR . . . .
H10D H 0.5372 0.1821 -0.2451 0.213 Uiso 1 1 calc GR . . . .
H10E H 0.3591 0.1403 -0.3006 0.213 Uiso 1 1 calc GR . . . .
C110 C 0.3968(11) 0.2550(10) -0.0597(8) 0.103(3) Uani 1 1 d . U . . .
H11A H 0.3119 0.2643 -0.1125 0.154 Uiso 1 1 calc GR . . . .
H11B H 0.4875 0.3282 -0.0412 0.154 Uiso 1 1 calc GR . . . .
H11C H 0.3754 0.2533 0.0177 0.154 Uiso 1 1 calc GR . . . .
C111 C 0.6119(7) 0.1979(6) 0.1807(6) 0.0526(14) Uani 1 1 d . U . . .
C112 C 0.7556(8) 0.4137(7) 0.2835(7) 0.0610(16) Uani 1 1 d . U . . .
C113 C 0.7590(7) 0.4049(6) 0.4019(6) 0.0564(15) Uani 1 1 d . U . . .
C114 C 0.6152(8) 0.1870(6) 0.2990(6) 0.0622(17) Uani 1 1 d . U . . .
H114 H 0.5641 0.1061 0.3019 0.075 Uiso 1 1 calc R . . . .
C115 C 0.8126(11) 0.5413(9) 0.1556(8) 0.103(3) Uani 1 1 d . U . . .
H11D H 0.8673 0.6298 0.1653 0.155 Uiso 1 1 calc R . . . .
H11E H 0.8551 0.4813 0.1076 0.155 Uiso 1 1 calc R . . . .
H11F H 0.7065 0.5188 0.1121 0.155 Uiso 1 1 calc R . . . .
C116 C 0.8360(9) 0.5159(7) 0.5253(7) 0.0696(18) Uani 1 1 d . U . . .
C117 C 0.8184(12) 0.4941(8) 0.6415(7) 0.097(3) Uani 1 1 d . U . . .
H117 H 0.7388 0.4124 0.6295 0.116 Uiso 1 1 calc R . . . .
C118 C 0.8473(11) 0.6085(8) 0.7602(7) 0.096(2) Uani 1 1 d . U . . .
H118 H 0.8796 0.6963 0.7555 0.115 Uiso 1 1 calc R . . . .
C119 C 0.9531(16) 0.5384(16) 0.7491(9) 0.167(5) Uani 1 1 d . U . . .
H11G H 0.9576 0.4828 0.7984 0.201 Uiso 1 1 calc R . . . .
H11H H 1.0510 0.5826 0.7404 0.201 Uiso 1 1 calc R . . . .
C120 C 0.7585(11) 0.5927(9) 0.8487(7) 0.105(3) Uani 1 1 d . U . . .
Cl12 Cl 0.2484(5) 0.9080(2) 0.4188(3) 0.1850(18) Uani 1 1 d . U . . .
F201 F 0.5371(10) 0.8979(5) 0.3596(6) 0.183(3) Uani 1 1 d . U . . .
F202 F 0.4454(6) 0.4511(6) 0.2846(5) 0.1163(17) Uani 1 1 d . U . . .
F203 F 0.4250(6) 0.4910(5) 0.5507(6) 0.1224(18) Uani 1 1 d . U . . .
O201 O -0.1287(6) -0.0099(4) 0.1097(4) 0.0760(13) Uani 1 1 d . U . . .
O202 O -0.1925(9) -0.0881(6) -0.1464(5) 0.118(2) Uani 1 1 d . U . . .
O203 O -0.3020(7) 0.1538(5) -0.4267(5) 0.0917(14) Uani 1 1 d . U . . .
H203 H -0.2906 0.2061 -0.4632 0.138 Uiso 1 1 calc GR . . . .
O204 O -0.0782(8) 0.1508(7) -0.4535(7) 0.132(2) Uani 1 1 d . U . . .
N201 N 0.1708(6) 0.4212(5) 0.3407(5) 0.0602(13) Uani 1 1 d . U . . .
N202 N 0.0145(6) 0.2037(5) 0.2225(5) 0.0569(13) Uani 1 1 d . U . . .
N203 N 0.0338(7) 0.2453(5) 0.0029(5) 0.0719(16) Uani 1 1 d . U . . .
C201 C 0.2156(10) 0.6538(7) 0.3788(7) 0.080(2) Uani 1 1 d . U . . .
H201 H 0.1231 0.6464 0.3982 0.096 Uiso 1 1 calc R . . . .
C202 C 0.3050(14) 0.7726(8) 0.3834(7) 0.105(3) Uani 1 1 d . U . . .
C203 C 0.4418(14) 0.7810(8) 0.3563(8) 0.109(3) Uani 1 1 d . U . . .
C204 C 0.4949(12) 0.6755(11) 0.3236(9) 0.117(3) Uani 1 1 d . U . . .
H204 H 0.5879 0.6841 0.3049 0.140 Uiso 1 1 calc R . . . .
C205 C 0.4032(10) 0.5573(9) 0.3200(8) 0.085(2) Uani 1 1 d . U . . .
C206 C 0.2624(8) 0.5449(7) 0.3454(6) 0.0669(18) Uani 1 1 d . U . . .
C207 C 0.1561(9) 0.4070(6) 0.4598(6) 0.0645(17) Uani 1 1 d . U . . .
H20A H 0.0646 0.3332 0.4419 0.077 Uiso 1 1 calc R . . . .
H20B H 0.1426 0.4859 0.5126 0.077 Uiso 1 1 calc R . . . .
C208 C 0.2932(9) 0.3846(7) 0.5340(7) 0.0752(19) Uani 1 1 d . U . . .
C209 C 0.2780(14) 0.3953(11) 0.6623(8) 0.121(3) Uani 1 1 d . U . . .
H20C H 0.2606 0.4764 0.7013 0.182 Uiso 1 1 calc GR . . . .
H20D H 0.3703 0.3941 0.7131 0.182 Uiso 1 1 calc GR . . . .
H20E H 0.1931 0.3223 0.6550 0.182 Uiso 1 1 calc GR . . . .
C210 C 0.3204(12) 0.2610(9) 0.4660(9) 0.105(3) Uani 1 1 d . U . . .
H21D H 0.2326 0.1863 0.4501 0.158 Uiso 1 1 calc GR . . . .
H21E H 0.4090 0.2545 0.5169 0.158 Uiso 1 1 calc GR . . . .
H21F H 0.3370 0.2627 0.3872 0.158 Uiso 1 1 calc GR . . . .
C211 C 0.0942(7) 0.3211(6) 0.2253(6) 0.0559(15) Uani 1 1 d . U . . .
C212 C -0.0517(7) 0.1084(6) 0.1122(6) 0.0557(15) Uani 1 1 d . U . . .
C213 C -0.0434(8) 0.1236(6) -0.0032(6) 0.0634(17) Uani 1 1 d . U . . .
C214 C 0.0971(8) 0.3420(7) 0.1119(6) 0.0696(19) Uani 1 1 d . U . . .
H214 H 0.1451 0.4263 0.1148 0.084 Uiso 1 1 calc R . . . .
C215 C -0.1324(10) -0.0258(7) 0.2272(8) 0.086(2) Uani 1 1 d . U . . .
H21A H -0.1943 -0.1144 0.2111 0.129 Uiso 1 1 calc GR . . . .
H21B H -0.1753 0.0352 0.2732 0.129 Uiso 1 1 calc GR . . . .
H21C H -0.0301 -0.0089 0.2762 0.129 Uiso 1 1 calc GR . . . .
C216 C -0.1061(10) 0.0211(8) -0.1277(7) 0.077(2) Uani 1 1 d . U . . .
C217 C -0.0672(10) 0.0535(8) -0.2357(7) 0.082(2) Uani 1 1 d . U . . .
H217 H 0.0187 0.1344 -0.2143 0.099 Uiso 1 1 calc R . . . .
C218 C -0.1972(10) 0.0188(7) -0.3512(7) 0.088(2) Uani 1 1 d . U . . .
H218 H -0.3003 -0.0259 -0.3496 0.106 Uiso 1 1 calc R . . . .
C219 C -0.0901(17) -0.0555(11) -0.3541(8) 0.145(4) Uani 1 1 d . U . . .
H21G H -0.0176 -0.0419 -0.4021 0.174 Uiso 1 1 calc R . . . .
H21H H -0.1274 -0.1449 -0.3561 0.174 Uiso 1 1 calc R . . . .
C220 C -0.1842(11) 0.1120(7) -0.4163(6) 0.0823(19) Uani 1 1 d . U . . .
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 117.3(6) . . ?
C120 O103 H103 109.5 . . ?
C106 N101 C107 117.9(6) . . ?
C111 N101 C106 120.2(5) . . ?
C111 N101 C107 121.8(5) . . ?
C112 N102 C111 118.4(5) . . ?
C114 N103 C113 119.6(5) . . ?
C102 C101 H101 120.0 . . ?
C106 C101 H101 120.0 . . ?
C106 C101 C102 120.0(7) . . ?
C101 C102 Cl11 120.0(7) . . ?
C103 C102 Cl11 121.8(6) . . ?
C103 C102 C101 118.2(7) . . ?
F101 C103 C102 116.7(8) . . ?
C104 C103 F101 121.2(8) . . ?
C104 C103 C102 122.1(7) . . ?
C103 C104 H104 120.5 . . ?
C103 C104 C105 118.9(8) . . ?
C105 C104 H104 120.5 . . ?
F102 C105 C104 117.6(7) . . ?
F102 C105 C106 119.1(6) . . ?
C106 C105 C104 123.3(8) . . ?
C101 C106 N101 120.9(6) . . ?
C105 C106 N101 121.6(6) . . ?
C105 C106 C101 117.4(6) . . ?
N101 C107 H10A 108.5 . . ?
N101 C107 H10B 108.5 . . ?
N101 C107 C108 115.0(6) . . ?
H10A C107 H10B 107.5 . . ?
C108 C107 H10A 108.5 . . ?
C108 C107 H10B 108.5 . . ?
F103 C108 C107 105.1(6) . . ?
F103 C108 C109 107.4(7) . . ?
F103 C108 C110 107.0(8) . . ?
C109 C108 C107 110.2(8) . . ?
C110 C108 C107 114.5(7) . . ?
C110 C108 C109 112.1(8) . . ?
C108 C109 H10C 109.5 . . ?
C108 C109 H10D 109.5 . . ?
C108 C109 H10E 109.5 . . ?
H10C C109 H10D 109.5 . . ?
H10C C109 H10E 109.5 . . ?
H10D C109 H10E 109.5 . . ?
C108 C110 H11A 109.5 . . ?
C108 C110 H11B 109.5 . . ?
C108 C110 H11C 109.5 . . ?
H11A C110 H11B 109.5 . . ?
H11A C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?
N101 C111 C114 122.5(6) . . ?
N102 C111 N101 118.2(5) . . ?
N102 C111 C114 119.3(6) . . ?
O101 C112 C113 118.1(6) . . ?
N102 C112 O101 118.8(5) . . ?
N102 C112 C113 123.0(5) . . ?
N103 C113 C112 117.9(6) . . ?
N103 C113 C116 116.9(5) . . ?
C112 C113 C116 125.2(5) . . ?
N103 C114 C111 121.8(5) . . ?
N103 C114 H114 119.1 . . ?
C111 C114 H114 119.1 . . ?
O101 C115 H11D 109.5 . . ?
O101 C115 H11E 109.5 . . ?
O101 C115 H11F 109.5 . . ?
H11D C115 H11E 109.5 . . ?
H11D C115 H11F 109.5 . . ?
H11E C115 H11F 109.5 . . ?
O102 C116 C113 122.1(6) . . ?
O102 C116 C117 119.0(7) . . ?
C117 C116 C113 118.9(6) . . ?
C116 C117 H117 115.7 . . ?
C116 C117 C118 120.4(7) . . ?
C118 C117 H117 115.7 . . ?
C119 C117 C116 119.4(9) . . ?
C119 C117 H117 115.7 . . ?
C119 C117 C118 57.5(6) . . ?
C117 C118 H118 116.4 . . ?
C119 C118 C117 59.8(6) . . ?
C119 C118 H118 116.4 . . ?
C119 C118 C120 116.4(10) . . ?
C120 C118 C117 119.6(7) . . ?
C120 C118 H118 116.4 . . ?
C117 C119 H11G 117.5 . . ?
C117 C119 H11H 117.5 . . ?
C118 C119 C117 62.7(7) . . ?
C118 C119 H11G 117.5 . . ?
C118 C119 H11H 117.5 . . ?
H11G C119 H11H 114.6 . . ?
O103 C120 C118 116.8(7) . . ?
O104 C120 O103 118.4(8) . . ?
O104 C120 C118 124.7(9) . . ?
C212 O201 C215 118.5(5) . . ?
C220 O203 H203 109.5 . . ?
C206 N201 C207 118.2(5) . . ?
C211 N201 C206 119.4(5) . . ?
C211 N201 C207 122.3(5) . . ?
C212 N202 C211 117.8(5) . . ?
C214 N203 C213 120.0(5) . . ?
C202 C201 H201 120.0 . . ?
C202 C201 C206 120.1(9) . . ?
C206 C201 H201 120.0 . . ?
C201 C202 Cl12 121.6(10) . . ?
C201 C202 C203 118.7(10) . . ?
C203 C202 Cl12 119.8(8) . . ?
F201 C203 C204 114.9(12) . . ?
C202 C203 F201 121.4(11) . . ?
C202 C203 C204 123.7(8) . . ?
C203 C204 H204 121.7 . . ?
C205 C204 C203 116.5(10) . . ?
C205 C204 H204 121.7 . . ?
F202 C205 C204 119.4(9) . . ?
F202 C205 C206 119.3(7) . . ?
C204 C205 C206 121.2(9) . . ?
C201 C206 N201 120.6(7) . . ?
C201 C206 C205 119.8(7) . . ?
C205 C206 N201 119.6(7) . . ?
N201 C207 H20A 108.7 . . ?
N201 C207 H20B 108.7 . . ?
N201 C207 C208 114.3(6) . . ?
H20A C207 H20B 107.6 . . ?
C208 C207 H20A 108.7 . . ?
C208 C207 H20B 108.7 . . ?
F203 C208 C207 106.2(5) . . ?
F203 C208 C209 107.2(7) . . ?
F203 C208 C210 106.4(7) . . ?
C209 C208 C207 109.3(7) . . ?
C210 C208 C207 114.0(6) . . ?
C210 C208 C209 113.2(7) . . ?
C208 C209 H20C 109.5 . . ?
C208 C209 H20D 109.5 . . ?
C208 C209 H20E 109.5 . . ?
H20C C209 H20D 109.5 . . ?
H20C C209 H20E 109.5 . . ?
H20D C209 H20E 109.5 . . ?
C208 C210 H21D 109.5 . . ?
C208 C210 H21E 109.5 . . ?
C208 C210 H21F 109.5 . . ?
H21D C210 H21E 109.5 . . ?
H21D C210 H21F 109.5 . . ?
H21E C210 H21F 109.5 . . ?
N201 C211 C214 121.1(6) . . ?
N202 C211 N201 118.8(5) . . ?
N202 C211 C214 120.2(6) . . ?
O201 C212 C213 118.8(6) . . ?
N202 C212 O201 117.7(6) . . ?
N202 C212 C213 123.5(5) . . ?
N203 C213 C212 117.1(6) . . ?
N203 C213 C216 116.3(6) . . ?
C212 C213 C216 126.5(6) . . ?
N203 C214 C211 121.2(6) . . ?
N203 C214 H214 119.4 . . ?
C211 C214 H214 119.4 . . ?
O201 C215 H21A 109.5 . . ?
O201 C215 H21B 109.5 . . ?
O201 C215 H21C 109.5 . . ?
H21A C215 H21B 109.5 . . ?
H21A C215 H21C 109.5 . . ?
H21B C215 H21C 109.5 . . ?
O202 C216 C213 122.0(7) . . ?
O202 C216 C217 119.8(7) . . ?
C213 C216 C217 118.1(6) . . ?
C216 C217 H217 116.4 . . ?
C216 C217 C218 117.6(7) . . ?
C218 C217 H217 116.4 . . ?
C219 C217 C216 118.8(8) . . ?
C219 C217 H217 116.4 . . ?
C219 C217 C218 58.9(6) . . ?
C217 C218 H218 116.8 . . ?
C219 C218 C217 59.5(6) . . ?
C219 C218 H218 116.8 . . ?
C220 C218 C217 116.4(7) . . ?
C220 C218 H218 116.8 . . ?
C220 C218 C219 118.1(9) . . ?
C217 C219 H21G 117.6 . . ?
C217 C219 H21H 117.6 . . ?
C218 C219 C217 61.6(6) . . ?
C218 C219 H21G 117.6 . . ?
C218 C219 H21H 117.6 . . ?
H21G C219 H21H 114.7 . . ?
O203 C220 C218 112.1(8) . . ?
O204 C220 O203 122.3(7) . . ?
O204 C220 C218 125.5(9) . . ?
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 1.715(8) . ?
F101 C103 1.351(8) . ?
F102 C105 1.340(8) . ?
F103 C108 1.409(9) . ?
O101 C112 1.346(8) . ?
O101 C115 1.458(9) . ?
O102 C116 1.210(9) . ?
O103 H103 0.8200 . ?
O103 C120 1.332(10) . ?
O104 C120 1.209(9) . ?
N101 C106 1.434(8) . ?
N101 C107 1.468(8) . ?
N101 C111 1.355(8) . ?
N102 C111 1.320(8) . ?
N102 C112 1.319(8) . ?
N103 C113 1.334(7) . ?
N103 C114 1.309(8) . ?
C101 H101 0.9300 . ?
C101 C102 1.395(10) . ?
C101 C106 1.393(9) . ?
C102 C103 1.370(11) . ?
C103 C104 1.330(11) . ?
C104 H104 0.9300 . ?
C104 C105 1.355(11) . ?
C105 C106 1.351(9) . ?
C107 H10A 0.9700 . ?
C107 H10B 0.9700 . ?
C107 C108 1.521(11) . ?
C108 C109 1.507(11) . ?
C108 C110 1.492(12) . ?
C109 H10C 0.9600 . ?
C109 H10D 0.9600 . ?
C109 H10E 0.9600 . ?
C110 H11A 0.9600 . ?
C110 H11B 0.9600 . ?
C110 H11C 0.9600 . ?
C111 C114 1.408(8) . ?
C112 C113 1.399(9) . ?
C113 C116 1.485(10) . ?
C114 H114 0.9300 . ?
C115 H11D 0.9600 . ?
C115 H11E 0.9600 . ?
C115 H11F 0.9600 . ?
C116 C117 1.471(11) . ?
C117 H117 0.9800 . ?
C117 C118 1.497(11) . ?
C117 C119 1.455(14) . ?
C118 H118 0.9800 . ?
C118 C119 1.421(14) . ?
C118 C120 1.463(11) . ?
C119 H11G 0.9700 . ?
C119 H11H 0.9700 . ?
Cl12 C202 1.703(11) . ?
F201 C203 1.378(9) . ?
F202 C205 1.329(10) . ?
F203 C208 1.424(8) . ?
O201 C212 1.333(7) . ?
O201 C215 1.431(9) . ?
O202 C216 1.220(9) . ?
O203 H203 0.8200 . ?
O203 C220 1.311(10) . ?
O204 C220 1.195(9) . ?
N201 C206 1.419(8) . ?
N201 C207 1.465(8) . ?
N201 C211 1.376(8) . ?
N202 C211 1.332(7) . ?
N202 C212 1.307(8) . ?
N203 C213 1.353(8) . ?
N203 C214 1.302(8) . ?
C201 H201 0.9300 . ?
C201 C202 1.367(11) . ?
C201 C206 1.380(10) . ?
C202 C203 1.370(15) . ?
C203 C204 1.382(15) . ?
C204 H204 0.9300 . ?
C204 C205 1.374(12) . ?
C205 C206 1.394(11) . ?
C207 H20A 0.9700 . ?
C207 H20B 0.9700 . ?
C207 C208 1.532(10) . ?
C208 C209 1.492(11) . ?
C208 C210 1.491(11) . ?
C209 H20C 0.9600 . ?
C209 H20D 0.9600 . ?
C209 H20E 0.9600 . ?
C210 H21D 0.9600 . ?
C210 H21E 0.9600 . ?
C210 H21F 0.9600 . ?
C211 C214 1.407(9) . ?
C212 C213 1.411(9) . ?
C213 C216 1.446(10) . ?
C214 H214 0.9300 . ?
C215 H21A 0.9600 . ?
C215 H21B 0.9600 . ?
C215 H21C 0.9600 . ?
C216 C217 1.488(10) . ?
C217 H217 0.9800 . ?
C217 C218 1.506(11) . ?
C217 C219 1.475(12) . ?
C218 H218 0.9800 . ?
C218 C219 1.465(14) . ?
C218 C220 1.460(10) . ?
C219 H21G 0.9700 . ?
C219 H21H 0.9700 . ?
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 O202 0.82 2.02 2.686(9) 138.0 1_666
O203 H203 N103 0.82 2.01 2.803(7) 162.7 1_454
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
Cl11 C102 C103 F101 -1.1(9) . . . . ?
Cl11 C102 C103 C104 178.5(6) . . . . ?
F101 C103 C104 C105 178.0(7) . . . . ?
F102 C105 C106 N101 -1.8(10) . . . . ?
F102 C105 C106 C101 179.4(6) . . . . ?
O101 C112 C113 N103 179.6(6) . . . . ?
O101 C112 C113 C116 -0.6(10) . . . . ?
O102 C116 C117 C118 20.7(14) . . . . ?
O102 C116 C117 C119 -46.7(13) . . . . ?
N101 C107 C108 F103 -58.4(9) . . . . ?
N101 C107 C108 C109 -173.9(8) . . . . ?
N101 C107 C108 C110 58.6(9) . . . . ?
N101 C111 C114 N103 -179.7(6) . . . . ?
N102 C111 C114 N103 0.3(10) . . . . ?
N102 C112 C113 N103 0.6(10) . . . . ?
N102 C112 C113 C116 -179.5(7) . . . . ?
N103 C113 C116 O102 174.2(8) . . . . ?
N103 C113 C116 C117 -5.4(10) . . . . ?
C101 C102 C103 F101 -179.8(6) . . . . ?
C101 C102 C103 C104 -0.1(11) . . . . ?
C102 C101 C106 N101 -178.5(6) . . . . ?
C102 C101 C106 C105 0.2(9) . . . . ?
C102 C103 C104 C105 -1.7(12) . . . . ?
C103 C104 C105 F102 -178.6(7) . . . . ?
C103 C104 C105 C106 2.9(13) . . . . ?
C104 C105 C106 N101 176.6(7) . . . . ?
C104 C105 C106 C101 -2.1(11) . . . . ?
C106 N101 C107 C108 77.3(8) . . . . ?
C106 N101 C111 N102 -168.2(6) . . . . ?
C106 N101 C111 C114 11.8(9) . . . . ?
C106 C101 C102 Cl11 -177.8(5) . . . . ?
C106 C101 C102 C103 0.9(10) . . . . ?
C107 N101 C106 C101 68.8(8) . . . . ?
C107 N101 C106 C105 -109.9(8) . . . . ?
C107 N101 C111 N102 8.6(9) . . . . ?
C107 N101 C111 C114 -171.3(7) . . . . ?
C111 N101 C106 C101 -114.2(7) . . . . ?
C111 N101 C106 C105 67.1(9) . . . . ?
C111 N101 C107 C108 -99.6(8) . . . . ?
C111 N102 C112 O101 -177.9(6) . . . . ?
C111 N102 C112 C113 1.1(10) . . . . ?
C112 N102 C111 N101 178.6(6) . . . . ?
C112 N102 C111 C114 -1.5(9) . . . . ?
C112 C113 C116 O102 -5.7(12) . . . . ?
C112 C113 C116 C117 174.7(7) . . . . ?
C113 N103 C114 C111 1.4(10) . . . . ?
C113 C116 C117 C118 -159.7(8) . . . . ?
C113 C116 C117 C119 132.9(9) . . . . ?
C114 N103 C113 C112 -1.8(9) . . . . ?
C114 N103 C113 C116 178.3(6) . . . . ?
C115 O101 C112 N102 3.0(10) . . . . ?
C115 O101 C112 C113 -176.0(7) . . . . ?
C116 C117 C118 C119 -107.6(12) . . . . ?
C116 C117 C118 C120 147.3(9) . . . . ?
C116 C117 C119 C118 109.3(8) . . . . ?
C117 C118 C120 O103 -153.8(10) . . . . ?
C117 C118 C120 O104 26.8(15) . . . . ?
C119 C117 C118 C120 -105.2(12) . . . . ?
C119 C118 C120 O103 137.6(11) . . . . ?
C119 C118 C120 O104 -41.8(14) . . . . ?
C120 C118 C119 C117 110.4(8) . . . . ?
Cl12 C202 C203 F201 1.4(11) . . . . ?
Cl12 C202 C203 C204 -178.3(7) . . . . ?
F201 C203 C204 C205 179.7(8) . . . . ?
F202 C205 C206 N201 3.8(11) . . . . ?
F202 C205 C206 C201 -178.2(7) . . . . ?
O201 C212 C213 N203 179.1(6) . . . . ?
O201 C212 C213 C216 -2.5(11) . . . . ?
O202 C216 C217 C218 47.7(11) . . . . ?
O202 C216 C217 C219 -20.0(13) . . . . ?
N201 C207 C208 F203 54.8(7) . . . . ?
N201 C207 C208 C209 170.1(7) . . . . ?
N201 C207 C208 C210 -62.0(8) . . . . ?
N201 C211 C214 N203 175.1(6) . . . . ?
N202 C211 C214 N203 -5.9(11) . . . . ?
N202 C212 C213 N203 -2.2(10) . . . . ?
N202 C212 C213 C216 176.2(7) . . . . ?
N203 C213 C216 O202 -171.3(8) . . . . ?
N203 C213 C216 C217 6.4(10) . . . . ?
C201 C202 C203 F201 -179.9(7) . . . . ?
C201 C202 C203 C204 0.4(13) . . . . ?
C202 C201 C206 N201 179.8(7) . . . . ?
C202 C201 C206 C205 1.9(11) . . . . ?
C202 C203 C204 C205 -0.6(14) . . . . ?
C203 C204 C205 F202 177.6(8) . . . . ?
C203 C204 C205 C206 1.4(13) . . . . ?
C204 C205 C206 N201 180.0(8) . . . . ?
C204 C205 C206 C201 -2.1(12) . . . . ?
C206 N201 C207 C208 -79.4(8) . . . . ?
C206 N201 C211 N202 176.9(6) . . . . ?
C206 N201 C211 C214 -4.2(10) . . . . ?
C206 C201 C202 Cl12 177.7(6) . . . . ?
C206 C201 C202 C203 -1.0(12) . . . . ?
C207 N201 C206 C201 -69.2(9) . . . . ?
C207 N201 C206 C205 108.7(8) . . . . ?
C207 N201 C211 N202 -5.9(9) . . . . ?
C207 N201 C211 C214 173.0(7) . . . . ?
C211 N201 C206 C201 108.1(8) . . . . ?
C211 N201 C206 C205 -74.0(9) . . . . ?
C211 N201 C207 C208 103.4(7) . . . . ?
C211 N202 C212 O201 178.6(6) . . . . ?
C211 N202 C212 C213 -0.1(9) . . . . ?
C212 N202 C211 N201 -177.0(6) . . . . ?
C212 N202 C211 C214 4.0(9) . . . . ?
C212 C213 C216 O202 10.3(13) . . . . ?
C212 C213 C216 C217 -172.0(7) . . . . ?
C213 N203 C214 C211 3.5(11) . . . . ?
C213 C216 C217 C218 -130.0(8) . . . . ?
C213 C216 C217 C219 162.2(9) . . . . ?
C214 N203 C213 C212 0.4(10) . . . . ?
C214 N203 C213 C216 -178.2(7) . . . . ?
C215 O201 C212 N202 -0.8(9) . . . . ?
C215 O201 C212 C213 177.9(7) . . . . ?
C216 C217 C218 C219 -108.6(9) . . . . ?
C216 C217 C218 C220 142.8(8) . . . . ?
C216 C217 C219 C218 106.6(8) . . . . ?
C217 C218 C220 O203 -123.7(8) . . . . ?
C217 C218 C220 O204 54.1(11) . . . . ?
C219 C217 C218 C220 -108.5(10) . . . . ?
C219 C218 C220 O203 168.4(8) . . . . ?
C219 C218 C220 O204 -13.8(12) . . . . ?
C220 C218 C219 C217 105.7(8) . . . . ?
