#------------------------------------------------------------------------------
#$Date: 2020-03-26 04:31:33 +0200 (Thu, 26 Mar 2020) $
#$Revision: 249721 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240201.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_7240201
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   mixed
_audit_creation_date             2016-02-10
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.01.25 svn.r3250 for OlexSys, GUI svn.r5148)
;
_audit_update_record
;
2020-02-07 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                103.187(4)
_cell_angle_beta                 105.203(4)
_cell_angle_gamma                104.668(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1429(4)
_cell_length_b                   11.0950(5)
_cell_length_c                   11.6725(5)
_cell_measurement_reflns_used    8769
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      29.8300
_cell_measurement_theta_min      2.1120
_cell_volume                     1048.93(9)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(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 0.998
_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 -30.00  129
  2  ω    -58.00  71.00   1.00   10.00    --  -19.00  72.00 150.00  129
  3  ω    -80.00  20.00   1.00   10.00    --  -19.00 -72.00-150.00  100
  4  ω    -69.00  20.00   1.00   10.00    --  -19.00 -72.00  30.00   89
  5  ω    -58.00  71.00   1.00   10.00    --  -19.00  72.00-120.00  129
  6  ω   -100.00 -14.00   1.00   10.00    --  -19.00   0.00-150.00   86
  7  ω    -58.00   5.00   1.00   10.00    --  -19.00  72.00  60.00   63
  8  ω    -15.00  10.00   1.00   10.00    --  -19.00 -54.00  60.00   25
  9  ω    -16.00  11.00   1.00   10.00    --  -19.00 -54.00-120.00   27
 10  ω    -35.00 -14.00   1.00   10.00    --  -19.00   0.00  30.00   21
 11  ω    -58.00 -37.00   1.00   10.00    --  -19.00  72.00 -90.00   21
 12  ω    -58.00 -37.00   1.00   10.00    --  -19.00  72.00   0.00   21
;
_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      0.0051985000
_diffrn_orient_matrix_UB_12      -0.0222133000
_diffrn_orient_matrix_UB_13      -0.0603240000
_diffrn_orient_matrix_UB_21      0.0698630000
_diffrn_orient_matrix_UB_22      -0.0147800000
_diffrn_orient_matrix_UB_23      0.0264933000
_diffrn_orient_matrix_UB_31      -0.0486026000
_diffrn_orient_matrix_UB_32      -0.0643261000
_diffrn_orient_matrix_UB_33      -0.0079223000
_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  0.0335
_diffrn_reflns_av_unetI/netI     0.0465
_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            21557
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         3.098
_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    0.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68962
_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    1.450
_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         0.289
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2597 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   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         10677
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0515
_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)+(0.0530P)²+0.1249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                7342
_reflns_number_total             10677
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00276c2.cif
_cod_data_source_block           2016scas0001_r_300k
_cod_original_cell_volume        1048.93(8)
_cod_database_code               7240201
_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 90.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.83
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H20A,H20B} of C207, {H11G,H11H} of C119, {H21G,H21H} of
  C219, {H10A,H10B} of C107
 At 1.5 times of:
  All C(H,H,H) groups, {H203,H103} of C220
2. Restrained distances
 O103-H103
 0.84 with sigma of 0.02
 O203-H203
 0.84 with sigma of 0.02
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 Aromatic/amide H refined with riding coordinates:
 C101(H101), C104(H104), C114(H114), C201(H201), C204(H204), C214(H214)
3.d Idealised Me refined as rotating group:
 C109(H10C,H10D,H10E), C110(H11A,H11B,H11C), C115(H11D,H11E,H11F), C209(H20C,
 H20D,H20E), C210(H21A,H21B,H21C), C215(H21D,H21E,H21F)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-09
_olex2_date_sample_submission    2016-01-26
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.042
_oxdiff_exptl_absorpt_empirical_full_min 0.552
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 0.41119(17) -0.39696(13) -0.02050(14) 0.0706(4) Uani 1 1 d . . . . .
F101 F 0.1354(4) -0.3740(3) 0.0483(3) 0.0737(10) Uani 1 1 d . . . . .
F102 F 0.2627(3) 0.0773(3) 0.1305(3) 0.0589(8) Uani 1 1 d . . . . .
F103 F 0.2453(3) 0.0283(3) -0.1393(3) 0.0653(9) Uani 1 1 d . . . . .
O101 O 0.8282(3) 0.5310(3) 0.2594(3) 0.0454(8) Uani 1 1 d . . . . .
O102 O 0.8479(5) 0.6177(3) 0.5073(3) 0.0762(11) Uani 1 1 d . . . . .
O103 O 0.9555(4) 0.3623(4) 0.8133(3) 0.0569(9) Uani 1 1 d D . . . .
O104 O 0.7321(5) 0.3872(5) 0.8407(4) 0.0798(12) Uani 1 1 d . . . . .
N101 N 0.5286(4) 0.0974(3) 0.0597(3) 0.0349(8) Uani 1 1 d . . . . .
N102 N 0.6835(4) 0.3149(3) 0.1607(3) 0.0337(8) Uani 1 1 d . . . . .
N103 N 0.7090(4) 0.2788(4) 0.3887(3) 0.0385(9) Uani 1 1 d . . . . .
C101 C 0.4691(5) -0.1371(4) 0.0265(4) 0.0382(10) Uani 1 1 d . . . . .
H101 H 0.5608 -0.1336 0.0050 0.046 Uiso 1 1 calc R . . . .
C102 C 0.3688(6) -0.2557(5) 0.0224(4) 0.0442(12) Uani 1 1 d . . . . .
C103 C 0.2333(5) -0.2585(5) 0.0536(5) 0.0498(13) Uani 1 1 d . . . . .
C104 C 0.1952(5) -0.1473(5) 0.0900(5) 0.0500(13) Uani 1 1 d . . . . .
H104 H 0.1033 -0.1503 0.1112 0.060 Uiso 1 1 calc R . . . .
C105 C 0.2977(5) -0.0320(5) 0.0939(4) 0.0412(11) Uani 1 1 d . . . . .
C106 C 0.4327(5) -0.0246(4) 0.0623(4) 0.0367(10) Uani 1 1 d . . . . .
C107 C 0.5268(5) 0.1090(5) -0.0619(4) 0.0405(11) Uani 1 1 d . . . . .
H10A H 0.5371 0.0299 -0.1103 0.049 Uiso 1 1 calc R . . . .
H10B H 0.6201 0.1820 -0.0501 0.049 Uiso 1 1 calc R . . . .
C108 C 0.3776(5) 0.1297(5) -0.1373(4) 0.0430(11) Uani 1 1 d . . . . .
C109 C 0.3711(7) 0.1069(7) -0.2705(5) 0.0665(16) Uani 1 1 d . . . . .
H10C H 0.3715 0.0197 -0.3047 0.100 Uiso 1 1 calc GR . . . .
H10D H 0.4630 0.1695 -0.2735 0.100 Uiso 1 1 calc GR . . . .
H10E H 0.2747 0.1168 -0.3185 0.100 Uiso 1 1 calc GR . . . .
C110 C 0.3604(6) 0.2575(6) -0.0790(5) 0.0566(14) Uani 1 1 d . . . . .
H11A H 0.2641 0.2648 -0.1304 0.085 Uiso 1 1 calc GR . . . .
H11B H 0.4517 0.3283 -0.0717 0.085 Uiso 1 1 calc GR . . . .
H11C H 0.3542 0.2616 0.0026 0.085 Uiso 1 1 calc GR . . . .
C111 C 0.6138(4) 0.1977(4) 0.1684(4) 0.0348(10) Uani 1 1 d . . . . .
C112 C 0.7589(5) 0.4127(4) 0.2649(4) 0.0364(10) Uani 1 1 d . . . . .
C113 C 0.7722(5) 0.3987(4) 0.3832(4) 0.0375(10) Uani 1 1 d . . . . .
C114 C 0.6294(5) 0.1793(5) 0.2849(4) 0.0404(11) Uani 1 1 d . . . . .
H114 H 0.5834 0.0963 0.2892 0.048 Uiso 1 1 calc R . . . .
C115 C 0.8141(6) 0.5450(5) 0.1384(5) 0.0560(14) Uani 1 1 d . . . . .
H11D H 0.7038 0.5305 0.0933 0.084 Uiso 1 1 calc GR . . . .
H11E H 0.8505 0.4819 0.0931 0.084 Uiso 1 1 calc GR . . . .
H11F H 0.8787 0.6319 0.1477 0.084 Uiso 1 1 calc GR . . . .
C116 C 0.8441(6) 0.5067(5) 0.5026(5) 0.0476(12) Uani 1 1 d . . . . .
C117 C 0.9119(5) 0.4735(4) 0.6164(4) 0.0443(9) Uani 1 1 d . . . . .
H117 H 0.9464 0.3962 0.6040 0.053 Uiso 1 1 calc R . . . .
C118 C 0.8480(6) 0.5017(5) 0.7227(4) 0.0555(11) Uani 1 1 d . . . . .
H118 H 0.7636 0.5419 0.7100 0.067 Uiso 1 1 calc R . . . .
C119 C 1.0098(6) 0.5842(5) 0.7321(4) 0.0646(13) Uani 1 1 d . . . . .
H11G H 1.0226 0.6724 0.7279 0.078 Uiso 1 1 calc R . . . .
H11H H 1.1030 0.5750 0.7875 0.078 Uiso 1 1 calc R . . . .
C120 C 0.8370(6) 0.4111(6) 0.7977(5) 0.0572(13) Uani 1 1 d . . . . .
Cl12 Cl 0.29819(18) 0.91063(13) 0.41355(15) 0.0726(4) Uani 1 1 d . . . . .
F201 F 0.5778(4) 0.8866(3) 0.3507(3) 0.0730(10) Uani 1 1 d . . . . .
F202 F 0.4423(3) 0.4346(3) 0.2612(3) 0.0613(8) Uani 1 1 d . . . . .
F203 F 0.4506(4) 0.4884(4) 0.5355(3) 0.0765(10) Uani 1 1 d . . . . .
O201 O -0.1303(4) -0.0185(3) 0.1300(3) 0.0506(9) Uani 1 1 d . . . . .
O202 O -0.2634(4) -0.0936(3) -0.1246(3) 0.0590(8) Uani 1 1 d . . . . .
N201 N 0.1725(4) 0.4149(4) 0.3251(4) 0.0389(9) Uani 1 1 d . . . . .
N202 N 0.0162(4) 0.1978(4) 0.2261(3) 0.0376(9) Uani 1 1 d . . . . .
N203 N -0.0046(4) 0.2308(4) -0.0026(4) 0.0409(9) Uani 1 1 d . . . . .
C201 C 0.2359(5) 0.6503(5) 0.3606(4) 0.0417(11) Uani 1 1 d . . . . .
H201 H 0.1422 0.6476 0.3788 0.050 Uiso 1 1 calc R . . . .
C202 C 0.3400(6) 0.7680(5) 0.3692(4) 0.0446(12) Uani 1 1 d . . . . .
C203 C 0.4763(6) 0.7712(5) 0.3427(5) 0.0491(13) Uani 1 1 d . . . . .
C204 C 0.5151(6) 0.6620(6) 0.3067(5) 0.0529(13) Uani 1 1 d . . . . .
H204 H 0.6095 0.6661 0.2893 0.063 Uiso 1 1 calc R . . . .
C205 C 0.4086(5) 0.5450(5) 0.2972(5) 0.0440(12) Uani 1 1 d . . . . .
C206 C 0.2699(5) 0.5359(4) 0.3251(4) 0.0357(10) Uani 1 1 d . . . . .
C207 C 0.1705(5) 0.4036(5) 0.4474(4) 0.0390(10) Uani 1 1 d . . . . .
H20A H 0.0775 0.3298 0.4343 0.047 Uiso 1 1 calc R . . . .
H20B H 0.1574 0.4821 0.4940 0.047 Uiso 1 1 calc R . . . .
C208 C 0.3174(6) 0.3856(5) 0.5253(5) 0.0487(12) Uani 1 1 d . . . . .
C209 C 0.3125(8) 0.3990(7) 0.6548(6) 0.0710(17) Uani 1 1 d . . . . .
H20C H 0.4089 0.3917 0.7058 0.107 Uiso 1 1 calc GR . . . .
H20D H 0.2209 0.3308 0.6513 0.107 Uiso 1 1 calc GR . . . .
H20E H 0.3045 0.4831 0.6903 0.107 Uiso 1 1 calc GR . . . .
C210 C 0.3433(8) 0.2606(7) 0.4679(6) 0.0691(17) Uani 1 1 d . . . . .
H21A H 0.3500 0.2578 0.3867 0.104 Uiso 1 1 calc GR . . . .
H21B H 0.2550 0.1868 0.4600 0.104 Uiso 1 1 calc GR . . . .
H21C H 0.4415 0.2572 0.5203 0.104 Uiso 1 1 calc GR . . . .
C211 C 0.0887(4) 0.3135(4) 0.2175(4) 0.0337(9) Uani 1 1 d . . . . .
C212 C -0.0628(5) 0.0992(5) 0.1217(4) 0.0357(10) Uani 1 1 d . . . . .
C213 C -0.0743(5) 0.1118(5) 0.0038(4) 0.0382(10) Uani 1 1 d . . . . .
C214 C 0.0755(5) 0.3291(5) 0.1000(4) 0.0411(11) Uani 1 1 d . . . . .
H214 H 0.1248 0.4111 0.0950 0.049 Uiso 1 1 calc R . . . .
C215 C -0.1080(6) -0.0289(6) 0.2530(6) 0.0591(15) Uani 1 1 d . . . . .
H21D H -0.1646 -0.1170 0.2469 0.089 Uiso 1 1 calc GR . . . .
H21E H -0.1490 0.0309 0.2975 0.089 Uiso 1 1 calc GR . . . .
H21F H 0.0045 -0.0075 0.2970 0.089 Uiso 1 1 calc GR . . . .
C216 C -0.1586(5) 0.0030(5) -0.1159(5) 0.0415(11) Uani 1 1 d . . . . .
O203 O -0.3166(4) 0.1553(3) -0.4366(3) 0.0500(8) Uani 1 1 d D . . A 1
O204 O -0.0876(4) 0.1226(4) -0.4384(4) 0.0667(10) Uani 1 1 d . . . A 1
C217 C -0.1126(5) 0.0215(4) -0.2238(4) 0.0459(10) Uani 1 1 d . . . A 1
H217 H -0.0075 0.0864 -0.2054 0.055 Uiso 1 1 calc R . . A 1
C218 C -0.2457(5) 0.0085(4) -0.3400(4) 0.0471(10) Uani 1 1 d . . . A 1
H218 H -0.3548 -0.0138 -0.3364 0.056 Uiso 1 1 calc R . . A 1
C219 C -0.1696(7) -0.0942(5) -0.3384(5) 0.0660(13) Uani 1 1 d . . . A 1
H21G H -0.0988 -0.1000 -0.3870 0.079 Uiso 1 1 calc R . . A 1
H21H H -0.2323 -0.1778 -0.3360 0.079 Uiso 1 1 calc R . . A 1
C220 C -0.2055(5) 0.0997(4) -0.4099(4) 0.0460(11) Uani 1 1 d . . . A 1
H203 H -0.297(6) 0.210(5) -0.477(5) 0.069 Uiso 1 1 d DR . . . .
H103 H 0.962(6) 0.320(5) 0.867(5) 0.069 Uiso 1 1 d DR . . . .
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 117.9(4) . . ?
C120 O103 H103 115(4) . . ?
C106 N101 C107 117.2(4) . . ?
C111 N101 C106 119.9(4) . . ?
C111 N101 C107 122.9(4) . . ?
C112 N102 C111 117.9(4) . . ?
C114 N103 C113 120.0(4) . . ?
C102 C101 H101 120.1 . . ?
C106 C101 H101 120.1 . . ?
C106 C101 C102 119.7(4) . . ?
C101 C102 Cl11 120.9(4) . . ?
C103 C102 Cl11 120.1(4) . . ?
C103 C102 C101 119.0(4) . . ?
F101 C103 C102 118.8(5) . . ?
F101 C103 C104 119.0(5) . . ?
C104 C103 C102 122.2(4) . . ?
C103 C104 H104 121.4 . . ?
C105 C104 C103 117.2(4) . . ?
C105 C104 H104 121.4 . . ?
F102 C105 C104 117.7(4) . . ?
F102 C105 C106 119.5(4) . . ?
C104 C105 C106 122.7(5) . . ?
C101 C106 N101 120.8(4) . . ?
C105 C106 N101 119.9(4) . . ?
C105 C106 C101 119.2(4) . . ?
N101 C107 H10A 108.5 . . ?
N101 C107 H10B 108.5 . . ?
N101 C107 C108 115.1(4) . . ?
H10A C107 H10B 107.5 . . ?
C108 C107 H10A 108.5 . . ?
C108 C107 H10B 108.5 . . ?
F103 C108 C107 105.7(4) . . ?
F103 C108 C109 106.3(4) . . ?
F103 C108 C110 107.4(4) . . ?
C109 C108 C107 109.7(4) . . ?
C110 C108 C107 113.3(4) . . ?
C110 C108 C109 113.9(4) . . ?
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 121.6(4) . . ?
N102 C111 N101 117.8(4) . . ?
N102 C111 C114 120.5(4) . . ?
O101 C112 C113 118.0(4) . . ?
N102 C112 O101 118.9(4) . . ?
N102 C112 C113 123.1(4) . . ?
N103 C113 C112 117.9(4) . . ?
N103 C113 C116 116.6(4) . . ?
C112 C113 C116 125.4(4) . . ?
N103 C114 C111 120.5(4) . . ?
N103 C114 H114 119.7 . . ?
C111 C114 H114 119.7 . . ?
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 121.4(4) . . ?
O102 C116 C117 121.5(4) . . ?
C113 C116 C117 117.0(4) . . ?
C116 C117 H117 116.4 . . ?
C116 C117 C118 118.9(4) . . ?
C118 C117 H117 116.4 . . ?
C119 C117 C116 117.1(4) . . ?
C119 C117 H117 116.4 . . ?
C119 C117 C118 59.9(3) . . ?
C117 C118 H118 116.0 . . ?
C119 C118 C117 59.1(3) . . ?
C119 C118 H118 116.0 . . ?
C120 C118 C117 118.9(4) . . ?
C120 C118 H118 116.0 . . ?
C120 C118 C119 119.0(5) . . ?
C117 C119 C118 61.1(3) . . ?
C117 C119 H11G 117.7 . . ?
C117 C119 H11H 117.7 . . ?
C118 C119 H11G 117.7 . . ?
C118 C119 H11H 117.7 . . ?
H11G C119 H11H 114.8 . . ?
O103 C120 C118 113.0(5) . . ?
O104 C120 O103 124.3(6) . . ?
O104 C120 C118 122.7(5) . . ?
C212 O201 C215 117.2(4) . . ?
C206 N201 C207 116.4(4) . . ?
C211 N201 C206 121.5(4) . . ?
C211 N201 C207 122.1(4) . . ?
C212 N202 C211 117.9(4) . . ?
C214 N203 C213 119.8(4) . . ?
C202 C201 H201 119.9 . . ?
C202 C201 C206 120.2(4) . . ?
C206 C201 H201 119.9 . . ?
C201 C202 Cl12 120.3(4) . . ?
C203 C202 Cl12 120.1(4) . . ?
C203 C202 C201 119.6(4) . . ?
F201 C203 C202 119.5(5) . . ?
F201 C203 C204 117.8(5) . . ?
C202 C203 C204 122.7(5) . . ?
C203 C204 H204 121.5 . . ?
C203 C204 C205 116.9(5) . . ?
C205 C204 H204 121.5 . . ?
F202 C205 C204 118.7(4) . . ?
F202 C205 C206 118.3(4) . . ?
C204 C205 C206 123.0(5) . . ?
C201 C206 N201 121.7(4) . . ?
C205 C206 N201 120.6(4) . . ?
C205 C206 C201 117.6(4) . . ?
N201 C207 H20A 108.5 . . ?
N201 C207 H20B 108.5 . . ?
N201 C207 C208 115.2(4) . . ?
H20A C207 H20B 107.5 . . ?
C208 C207 H20A 108.5 . . ?
C208 C207 H20B 108.5 . . ?
F203 C208 C207 107.3(4) . . ?
F203 C208 C209 107.1(4) . . ?
F203 C208 C210 106.4(4) . . ?
C207 C208 C210 113.7(4) . . ?
C209 C208 C207 109.5(4) . . ?
C209 C208 C210 112.4(5) . . ?
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 H21A 109.5 . . ?
C208 C210 H21B 109.5 . . ?
C208 C210 H21C 109.5 . . ?
H21A C210 H21B 109.5 . . ?
H21A C210 H21C 109.5 . . ?
H21B C210 H21C 109.5 . . ?
N201 C211 C214 121.8(4) . . ?
N202 C211 N201 118.1(4) . . ?
N202 C211 C214 120.1(4) . . ?
O201 C212 C213 118.9(4) . . ?
N202 C212 O201 118.1(4) . . ?
N202 C212 C213 122.9(4) . . ?
N203 C213 C212 118.0(4) . . ?
N203 C213 C216 117.3(4) . . ?
C212 C213 C216 124.8(4) . . ?
N203 C214 C211 121.2(4) . . ?
N203 C214 H214 119.4 . . ?
C211 C214 H214 119.4 . . ?
O201 C215 H21D 109.5 . . ?
O201 C215 H21E 109.5 . . ?
O201 C215 H21F 109.5 . . ?
H21D C215 H21E 109.5 . . ?
H21D C215 H21F 109.5 . . ?
H21E C215 H21F 109.5 . . ?
O202 C216 C213 121.4(4) . . ?
O202 C216 C217 122.0(4) . . ?
C217 C216 C213 116.6(4) . . ?
C220 O203 H203 114(4) . . ?
C216 C217 H217 116.7 . . ?
C216 C217 C218 117.2(4) . . ?
C216 C217 C219 118.3(4) . . ?
C218 C217 H217 116.7 . . ?
C219 C217 H217 116.7 . . ?
C219 C217 C218 58.9(3) . . ?
C217 C218 H218 116.5 . . ?
C219 C218 C217 59.7(3) . . ?
C219 C218 H218 116.5 . . ?
C220 C218 C217 116.5(4) . . ?
C220 C218 H218 116.5 . . ?
C220 C218 C219 118.9(4) . . ?
C217 C219 H21G 117.6 . . ?
C217 C219 H21H 117.6 . . ?
C218 C219 C217 61.4(3) . . ?
C218 C219 H21G 117.6 . . ?
C218 C219 H21H 117.6 . . ?
H21G C219 H21H 114.7 . . ?
O203 C220 C218 111.3(4) . . ?
O204 C220 O203 123.6(5) . . ?
O204 C220 C218 125.1(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 1.706(5) . ?
F101 C103 1.342(5) . ?
F102 C105 1.337(5) . ?
F103 C108 1.418(5) . ?
O101 C112 1.329(5) . ?
O101 C115 1.431(6) . ?
O102 C116 1.212(6) . ?
O103 C120 1.318(6) . ?
O103 H103 0.86(3) . ?
O104 C120 1.194(6) . ?
N101 C106 1.426(6) . ?
N101 C107 1.450(6) . ?
N101 C111 1.362(5) . ?
N102 C111 1.330(5) . ?
N102 C112 1.309(6) . ?
N103 C113 1.334(6) . ?
N103 C114 1.318(6) . ?
C101 H101 0.9300 . ?
C101 C102 1.383(7) . ?
C101 C106 1.375(7) . ?
C102 C103 1.375(7) . ?
C103 C104 1.371(8) . ?
C104 H104 0.9300 . ?
C104 C105 1.364(7) . ?
C105 C106 1.367(6) . ?
C107 H10A 0.9700 . ?
C107 H10B 0.9700 . ?
C107 C108 1.520(6) . ?
C108 C109 1.500(8) . ?
C108 C110 1.493(8) . ?
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 1.396(6) . ?
C112 C113 1.401(6) . ?
C113 C116 1.473(7) . ?
C114 H114 0.9300 . ?
C115 H11D 0.9600 . ?
C115 H11E 0.9600 . ?
C115 H11F 0.9600 . ?
C116 C117 1.481(7) . ?
C117 H117 0.9800 . ?
C117 C118 1.507(6) . ?
C117 C119 1.478(6) . ?
C118 H118 0.9800 . ?
C118 C119 1.490(7) . ?
C118 C120 1.478(7) . ?
C119 H11G 0.9700 . ?
C119 H11H 0.9700 . ?
Cl12 C202 1.719(5) . ?
F201 C203 1.344(6) . ?
F202 C205 1.340(5) . ?
F203 C208 1.399(6) . ?
O201 C212 1.333(6) . ?
O201 C215 1.431(7) . ?
O202 C216 1.206(5) . ?
N201 C206 1.411(6) . ?
N201 C207 1.465(6) . ?
N201 C211 1.358(6) . ?
N202 C211 1.327(5) . ?
N202 C212 1.316(6) . ?
N203 C213 1.341(6) . ?
N203 C214 1.303(6) . ?
C201 H201 0.9300 . ?
C201 C202 1.372(7) . ?
C201 C206 1.381(7) . ?
C202 C203 1.354(7) . ?
C203 C204 1.354(8) . ?
C204 H204 0.9300 . ?
C204 C205 1.372(7) . ?
C205 C206 1.376(6) . ?
C207 H20A 0.9700 . ?
C207 H20B 0.9700 . ?
C207 C208 1.500(6) . ?
C208 C209 1.498(8) . ?
C208 C210 1.502(8) . ?
C209 H20C 0.9600 . ?
C209 H20D 0.9600 . ?
C209 H20E 0.9600 . ?
C210 H21A 0.9600 . ?
C210 H21B 0.9600 . ?
C210 H21C 0.9600 . ?
C211 C214 1.399(6) . ?
C212 C213 1.394(6) . ?
C213 C216 1.482(7) . ?
C214 H214 0.9300 . ?
C215 H21D 0.9600 . ?
C215 H21E 0.9600 . ?
C215 H21F 0.9600 . ?
C216 C217 1.469(7) . ?
O203 C220 1.323(6) . ?
O203 H203 0.86(3) . ?
O204 C220 1.193(6) . ?
C217 H217 0.9800 . ?
C217 C218 1.516(5) . ?
C217 C219 1.490(6) . ?
C218 H218 0.9800 . ?
C218 C219 1.479(7) . ?
C218 C220 1.474(6) . ?
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
O203 H203 N103 0.86(3) 1.90(3) 2.729(5) 161(6) 1_454
O103 H103 N203 0.86(3) 2.00(3) 2.859(5) 176(5) 1_656
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 -0.6(6) . . . . ?
Cl11 C102 C103 C104 179.3(4) . . . . ?
F101 C103 C104 C105 -179.9(4) . . . . ?
F102 C105 C106 N101 -4.6(7) . . . . ?
F102 C105 C106 C101 179.1(4) . . . . ?
O101 C112 C113 N103 -176.9(4) . . . . ?
O101 C112 C113 C116 6.0(7) . . . . ?
O102 C116 C117 C118 58.2(6) . . . . ?
O102 C116 C117 C119 -10.6(7) . . . . ?
N101 C107 C108 F103 -51.9(5) . . . . ?
N101 C107 C108 C109 -166.1(4) . . . . ?
N101 C107 C108 C110 65.4(5) . . . . ?
N101 C111 C114 N103 -178.2(4) . . . . ?
N102 C111 C114 N103 2.3(6) . . . . ?
N102 C112 C113 N103 2.2(6) . . . . ?
N102 C112 C113 C116 -174.9(4) . . . . ?
N103 C113 C116 O102 -151.2(5) . . . . ?
N103 C113 C116 C117 29.0(6) . . . . ?
C101 C102 C103 F101 179.3(4) . . . . ?
C101 C102 C103 C104 -0.8(7) . . . . ?
C102 C101 C106 N101 -176.0(4) . . . . ?
C102 C101 C106 C105 0.2(7) . . . . ?
C102 C103 C104 C105 0.2(7) . . . . ?
C103 C104 C105 F102 -179.3(4) . . . . ?
C103 C104 C105 C106 0.6(7) . . . . ?
C104 C105 C106 N101 175.5(4) . . . . ?
C104 C105 C106 C101 -0.8(7) . . . . ?
C106 N101 C107 C108 76.9(5) . . . . ?
C106 N101 C111 N102 -170.9(4) . . . . ?
C106 N101 C111 C114 9.5(6) . . . . ?
C106 C101 C102 Cl11 -179.5(3) . . . . ?
C106 C101 C102 C103 0.5(7) . . . . ?
C107 N101 C106 C101 66.5(5) . . . . ?
C107 N101 C106 C105 -109.8(5) . . . . ?
C107 N101 C111 N102 7.5(6) . . . . ?
C107 N101 C111 C114 -172.0(4) . . . . ?
C111 N101 C106 C101 -115.0(5) . . . . ?
C111 N101 C106 C105 68.8(5) . . . . ?
C111 N101 C107 C108 -101.6(5) . . . . ?
C111 N102 C112 O101 -179.4(4) . . . . ?
C111 N102 C112 C113 1.5(6) . . . . ?
C112 N102 C111 N101 176.8(4) . . . . ?
C112 N102 C111 C114 -3.7(6) . . . . ?
C112 C113 C116 O102 25.9(8) . . . . ?
C112 C113 C116 C117 -153.9(4) . . . . ?
C113 N103 C114 C111 1.6(6) . . . . ?
C113 C116 C117 C118 -122.1(5) . . . . ?
C113 C116 C117 C119 169.1(4) . . . . ?
C114 N103 C113 C112 -3.7(6) . . . . ?
C114 N103 C113 C116 173.7(4) . . . . ?
C115 O101 C112 N102 0.9(6) . . . . ?
C115 O101 C112 C113 -179.9(4) . . . . ?
C116 C117 C118 C119 -106.4(5) . . . . ?
C116 C117 C118 C120 145.3(4) . . . . ?
C116 C117 C119 C118 109.3(5) . . . . ?
C117 C118 C120 O103 35.5(6) . . . . ?
C117 C118 C120 O104 -145.6(5) . . . . ?
C119 C117 C118 C120 -108.3(5) . . . . ?
C119 C118 C120 O103 -33.0(6) . . . . ?
C119 C118 C120 O104 145.8(5) . . . . ?
C120 C118 C119 C117 108.2(5) . . . . ?
Cl12 C202 C203 F201 -0.4(7) . . . . ?
Cl12 C202 C203 C204 -179.7(4) . . . . ?
F201 C203 C204 C205 -179.0(4) . . . . ?
F202 C205 C206 N201 4.7(7) . . . . ?
F202 C205 C206 C201 -179.3(4) . . . . ?
O201 C212 C213 N203 -179.5(4) . . . . ?
O201 C212 C213 C216 0.6(6) . . . . ?
O202 C216 C217 C218 53.2(6) . . . . ?
O202 C216 C217 C219 -14.3(6) . . . . ?
N201 C207 C208 F203 54.3(5) . . . . ?
N201 C207 C208 C209 170.2(5) . . . . ?
N201 C207 C208 C210 -63.2(6) . . . . ?
N201 C211 C214 N203 179.7(4) . . . . ?
N202 C211 C214 N203 -1.5(6) . . . . ?
N202 C212 C213 N203 -1.6(6) . . . . ?
N202 C212 C213 C216 178.5(4) . . . . ?
N203 C213 C216 O202 -156.7(4) . . . . ?
N203 C213 C216 C217 20.8(5) . . . . ?
C201 C202 C203 F201 179.8(4) . . . . ?
C201 C202 C203 C204 0.5(8) . . . . ?
C202 C201 C206 N201 174.8(4) . . . . ?
C202 C201 C206 C205 -1.1(7) . . . . ?
C202 C203 C204 C205 0.3(8) . . . . ?
C203 C204 C205 F202 179.7(5) . . . . ?
C203 C204 C205 C206 -1.6(8) . . . . ?
C204 C205 C206 N201 -174.0(4) . . . . ?
C204 C205 C206 C201 2.0(7) . . . . ?
C206 N201 C207 C208 -75.7(5) . . . . ?
C206 N201 C211 N202 171.6(4) . . . . ?
C206 N201 C211 C214 -9.5(6) . . . . ?
C206 C201 C202 Cl12 -179.9(3) . . . . ?
C206 C201 C202 C203 -0.1(7) . . . . ?
C207 N201 C206 C201 -66.1(5) . . . . ?
C207 N201 C206 C205 109.7(5) . . . . ?
C207 N201 C211 N202 -6.6(6) . . . . ?
C207 N201 C211 C214 172.3(4) . . . . ?
C211 N201 C206 C201 115.6(5) . . . . ?
C211 N201 C206 C205 -68.6(6) . . . . ?
C211 N201 C207 C208 102.6(5) . . . . ?
C211 N202 C212 O201 177.3(3) . . . . ?
C211 N202 C212 C213 -0.6(6) . . . . ?
C212 N202 C211 N201 -179.0(4) . . . . ?
C212 N202 C211 C214 2.1(6) . . . . ?
C212 C213 C216 O202 23.1(6) . . . . ?
C212 C213 C216 C217 -159.3(4) . . . . ?
C213 N203 C214 C211 -0.9(6) . . . . ?
C213 C216 C217 C218 -124.3(4) . . . . ?
C213 C216 C217 C219 168.2(4) . . . . ?
C214 N203 C213 C212 2.3(6) . . . . ?
C214 N203 C213 C216 -177.8(4) . . . . ?
C215 O201 C212 N202 -1.4(6) . . . . ?
C215 O201 C212 C213 176.5(4) . . . . ?
C216 C217 C218 C219 -108.2(5) . . . . ?
C216 C217 C218 C220 142.2(4) . . . . ?
C216 C217 C219 C218 106.3(4) . . . . ?
C217 C218 C220 O203 -132.0(4) . . . . ?
C217 C218 C220 O204 47.3(6) . . . . ?
C219 C217 C218 C220 -109.5(5) . . . . ?
C219 C218 C220 O203 159.7(4) . . . . ?
C219 C218 C220 O204 -21.0(7) . . . . ?
C220 C218 C219 C217 105.5(4) . . . . ?
