# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2016scas0001_R_100K
_database_code_depnum_ccdc_archive 'CCDC 1982526'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '2(C20 H19 Cl F3 N3 O4), 0.5(H2 O)'
_chemical_formula_sum            'C40 H39 Cl2 F6 N6 O8.50'
_exptl_crystal_recrystallization_method 
'the material was recrystallized from --- by slow evaporation'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_pressure         101.3
_chemical_formula_weight         924.66

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_chemical_absolute_configuration ad

loop_
_space_group_symop_operation_xyz
'x, y, z'

_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.
;

_cell_length_a                   9.0757(3)
_cell_length_b                   11.0502(4)
_cell_length_c                   11.7199(5)
_cell_angle_alpha                103.378(3)
_cell_angle_beta                 105.493(3)
_cell_angle_gamma                104.407(3)
_cell_volume                     1039.68(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10496
_cell_measurement_theta_min      3.109
_cell_measurement_theta_max      28.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_F_000             477
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5638
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating anode'
_diffrn_source_type              'Rotating anode'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            25300
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.109
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             10496
_reflns_number_gt                8772
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.972

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 3.1 (Rigaku, 2013)'
_computing_cell_refinement       
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)'
_computing_data_reduction        
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.0049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_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_number_reflns         10496
_refine_ls_number_parameters     583
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

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

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.055



_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2016scas0001_r_300k
_database_code_depnum_ccdc_archive 'CCDC 1982527'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;
_audit_creation_date             2016-02-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.01.25 svn.r3250 for OlexSys, GUI svn.r5148)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 Cl F3 N3 O4'
_chemical_formula_sum            'C20 H19 Cl F3 N3 O4'
_chemical_formula_weight         457.83
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.1429(4)
_cell_length_b                   11.0950(5)
_cell_length_c                   11.6725(5)
_cell_angle_alpha                103.187(4)
_cell_angle_beta                 105.203(4)
_cell_angle_gamma                104.668(4)
_cell_volume                     1048.93(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8769
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      29.8300
_cell_measurement_theta_min      2.1120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_preparation       ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_device_type2 'Rigaku AFC12 (Right)'
_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_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
_diffrn_special_details          ?
_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_odcompleteness_completeness 90.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.83
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.021
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2016scas0001_r_410k
_database_code_depnum_ccdc_archive 'CCDC 1982528'
loop_
_audit_author_name
_audit_author_address
'Okky Dwichandra Putra'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-03-24 downloaded from the CCDC.
;
_audit_creation_date             2016-02-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.16 svn.r3264 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 Cl F3 N3 O4'
_chemical_formula_sum            'C20 H19 Cl F3 N3 O4'
_chemical_formula_weight         457.83
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.4219(6)
_cell_length_b                   11.2659(6)
_cell_length_c                   11.5862(6)
_cell_angle_alpha                107.504(4)
_cell_angle_beta                 100.890(5)
_cell_angle_gamma                104.746(5)
_cell_volume                     1086.25(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5840
_cell_measurement_temperature    410(2)
_cell_measurement_theta_max      28.6190
_cell_measurement_theta_min      2.2750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_device_type2 'Rigaku AFC12 (Right)'
_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_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
_diffrn_special_details          ?
_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_odcompleteness_completeness 90.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.80
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)
;
_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_coef       .
_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_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.020
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_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
