# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_zhaoxy_fv2_181128
_database_code_depnum_ccdc_archive 'CCDC 1885831'
loop_
_audit_author_name
_audit_author_address
'Xiaoyun Zhao'
;Sun Yat-sen Univeisity
China
;
_audit_update_record             
;
2018-12-18 deposited with the CCDC.	2019-04-22 downloaded from the CCDC.
;
_audit_creation_date             2018-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H27 Br F3 N3 O3'
_chemical_formula_sum            'C35 H27 Br F3 N3 O3'
_chemical_formula_weight         674.50
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.47950(10)
_cell_length_b                   18.03580(10)
_cell_length_c                   21.54370(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3294.78(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23741
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.7980
_cell_measurement_theta_min      3.1730
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.562
_exptl_absorpt_coefficient_mu    2.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31862
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.867
_diffrn_reflns_theta_min         3.196
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  30.00   0.50    0.05    --  -46.62  13.00  49.00  190
  2  ω   -117.00 -27.00   0.50    0.05    -- -100.00 125.00-112.00  180
  3  ω     34.00 112.00   0.50    0.05    --  107.00-116.00  73.00  156
  4  ω     31.00 126.00   0.50    0.05    --  107.00 -13.00-121.00  190
  5  ω     32.00 120.00   0.50    0.05    --   46.62  38.00 -30.00  176
  6  ω    -27.00  61.00   0.50    0.05    --   46.62 -38.00 120.00  176
  7  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 -30.00  150
  8  ω     93.00 178.00   0.50    0.05    --  107.00  45.00-180.00  170
  9  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 120.00  150
 10  ω     32.00 123.00   0.50    0.05    --  107.00 -30.00 -30.00  182
 11  ω     92.00 178.00   0.50    0.05    --  107.00  30.00 120.00  172
 12  ω     34.00 125.00   0.50    0.05    --  107.00 -61.00   0.00  182
 13  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00-180.00  150
 14  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00   0.00  150
 15  ω     34.00 117.00   0.50    0.05    --  107.00-125.00-150.00  166
 16  ω     75.00 125.00   0.50    0.05    --  107.00 -61.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0255371000
_diffrn_orient_matrix_UB_12      -0.0750609000
_diffrn_orient_matrix_UB_13      -0.0326485000
_diffrn_orient_matrix_UB_21      -0.0186827000
_diffrn_orient_matrix_UB_22      -0.0403060000
_diffrn_orient_matrix_UB_23      0.0626354000
_diffrn_orient_matrix_UB_31      -0.1788170000
_diffrn_orient_matrix_UB_32      -0.0064971000
_diffrn_orient_matrix_UB_33      -0.0112164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6670
_reflns_number_total             6858
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.903
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 
;
 Flack x determined using 2766 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.171(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6858
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.041
_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)+(0.0758P)²+11.5344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00I), C00M(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C011(H01A,H01B), C019(H01C,H01D)
2.c Aromatic/amide H refined with riding coordinates:
 N00C(H00C), C00H(H00H), C00J(H00J), C00N(H00N), C00Q(H00Q), C00S(H00S),
 C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C012(H012),
 C014(H014), C015(H015), C016(H016), C017(H017), C018(H018), C01A(H01E),
 C01B(H01F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br01 Br 0.68726(9) 0.83060(4) 0.43036(3) 0.02698(17) Uani 1 1 d . . . . .
F004 F 0.9358(5) 0.5258(2) 0.51818(16) 0.0276(8) Uani 1 1 d . . . . .
F005 F 1.0405(5) 0.4515(3) 0.58460(18) 0.0358(10) Uani 1 1 d . . . . .
F006 F 0.8108(6) 0.4278(2) 0.54584(18) 0.0340(9) Uani 1 1 d . . . . .
O007 O 0.8606(5) 0.6334(2) 0.7256(2) 0.0216(9) Uani 1 1 d . . . . .
O008 O 0.1680(5) 0.5104(3) 0.7100(2) 0.0270(10) Uani 1 1 d . . . . .
O009 O 0.4205(5) 0.4480(2) 0.63318(19) 0.0207(9) Uani 1 1 d . . . . .
N00A N 0.3434(6) 0.6075(3) 0.7140(2) 0.0196(10) Uani 1 1 d . . . . .
N00B N 0.7715(6) 0.5696(3) 0.8116(2) 0.0201(10) Uani 1 1 d . . . . .
N00C N 0.8049(6) 0.4804(3) 0.6724(2) 0.0184(9) Uani 1 1 d . . . . .
H00C H 0.844629 0.436013 0.678892 0.022 Uiso 1 1 calc R . . . .
C00D C 0.2949(7) 0.5393(4) 0.6988(2) 0.0197(12) Uani 1 1 d . . . . .
C00E C 0.4314(7) 0.5055(3) 0.6622(3) 0.0202(12) Uani 1 1 d . . . . .
C00F C 0.5009(7) 0.6291(3) 0.6894(3) 0.0186(11) Uani 1 1 d . . . . .
H00A H 0.566124 0.651983 0.722369 0.022 Uiso 1 1 calc R . . . .
H00B H 0.490149 0.664657 0.654673 0.022 Uiso 1 1 calc R . . . .
C00G C 0.7875(6) 0.5833(3) 0.7495(2) 0.0151(10) Uani 1 1 d . . . . .
C00H C 1.0589(8) 0.5077(4) 0.8616(3) 0.0231(12) Uani 1 1 d . . . . .
H00H H 1.029117 0.494369 0.820602 0.028 Uiso 1 1 calc R . . . .
C00I C 0.8320(7) 0.5276(3) 0.6187(3) 0.0191(11) Uani 1 1 d . . . . .
H00I H 0.902101 0.570161 0.629922 0.023 Uiso 1 1 calc R . . . .
C00J C 0.5603(8) 0.4058(4) 0.7665(3) 0.0225(12) Uani 1 1 d . . . . .
H00J H 0.526693 0.384129 0.728587 0.027 Uiso 1 1 calc R . . . .
C00K C 0.5749(7) 0.5560(3) 0.6670(3) 0.0188(11) Uani 1 1 d . . . . .
C00L C 0.6662(7) 0.6259(3) 0.5637(3) 0.0175(11) Uani 1 1 d . . . . .
C00M C 0.6654(7) 0.5555(3) 0.6025(3) 0.0171(11) Uani 1 1 d . . . . .
H00M H 0.614994 0.516139 0.576580 0.021 Uiso 1 1 calc R . . . .
C00N C 0.7277(7) 0.6932(3) 0.5844(3) 0.0187(12) Uani 1 1 d . . . . .
H00N H 0.766924 0.697230 0.625586 0.022 Uiso 1 1 calc R . . . .
C00O C 0.9043(7) 0.4827(3) 0.5667(3) 0.0207(11) Uani 1 1 d . . . . .
C00P C 0.3095(8) 0.6839(3) 0.8084(3) 0.0211(12) Uani 1 1 d . . . . .
C00Q C 0.6600(7) 0.4697(4) 0.8788(3) 0.0216(12) Uani 1 1 d . . . . .
H00Q H 0.695843 0.491550 0.916374 0.026 Uiso 1 1 calc R . . . .
C00R C 0.6776(8) 0.7478(3) 0.4853(3) 0.0218(12) Uani 1 1 d . . . . .
C00S C 0.6176(7) 0.6814(3) 0.4630(3) 0.0209(12) Uani 1 1 d . . . . .
H00S H 0.582438 0.677289 0.421267 0.025 Uiso 1 1 calc R . . . .
C00T C 0.9834(7) 0.5659(4) 0.8913(3) 0.0216(12) Uani 1 1 d . . . . .
C00U C 0.7320(7) 0.7547(4) 0.5453(3) 0.0229(13) Uani 1 1 d . . . . .
H00U H 0.771990 0.800735 0.559790 0.027 Uiso 1 1 calc R . . . .
C00V C 0.5770(8) 0.4024(4) 0.8789(3) 0.0259(14) Uani 1 1 d . . . . .
H00V H 0.552406 0.378977 0.917142 0.031 Uiso 1 1 calc R . . . .
C00W C 1.0259(8) 0.5847(4) 0.9518(3) 0.0263(14) Uani 1 1 d . . . . .
H00W H 0.972083 0.623441 0.972824 0.032 Uiso 1 1 calc R . . . .
C00X C 0.6377(7) 0.4722(4) 0.7660(3) 0.0206(12) Uani 1 1 d . . . . .
C00Y C 0.5301(8) 0.3695(4) 0.8228(3) 0.0265(13) Uani 1 1 d . . . . .
H00Y H 0.478046 0.322879 0.822953 0.032 Uiso 1 1 calc R . . . .
C00Z C 0.3790(8) 0.6316(4) 0.8472(3) 0.0248(13) Uani 1 1 d . . . . .
H00Z H 0.390193 0.581780 0.833530 0.030 Uiso 1 1 calc R . . . .
C010 C 0.6878(7) 0.5031(3) 0.8223(3) 0.0184(11) Uani 1 1 d . . . . .
C011 C 0.8568(8) 0.6109(4) 0.8590(3) 0.0237(13) Uani 1 1 d . . . . .
H01A H 0.780741 0.628849 0.890398 0.028 Uiso 1 1 calc R . . . .
H01B H 0.906322 0.654801 0.839485 0.028 Uiso 1 1 calc R . . . .
C012 C 0.6101(7) 0.6213(3) 0.5029(3) 0.0191(11) Uani 1 1 d . . . . .
H012 H 0.565779 0.576076 0.488553 0.023 Uiso 1 1 calc R . . . .
C013 C 0.6988(7) 0.5211(3) 0.7136(2) 0.0174(11) Uani 1 1 d . . . . .
C014 C 1.1779(9) 0.4688(4) 0.8915(3) 0.0315(14) Uani 1 1 d . . . . .
H014 H 1.228933 0.428743 0.871074 0.038 Uiso 1 1 calc R . . . .
C015 C 0.4147(10) 0.7234(5) 0.9260(4) 0.0427(19) Uani 1 1 d . . . . .
H015 H 0.449412 0.737006 0.966378 0.051 Uiso 1 1 calc R . . . .
C016 C 1.1474(8) 0.5466(5) 0.9813(3) 0.0332(16) Uani 1 1 d . . . . .
H016 H 1.179082 0.560380 1.022009 0.040 Uiso 1 1 calc R . . . .
C017 C 0.2923(8) 0.7565(4) 0.8290(3) 0.0276(13) Uani 1 1 d . . . . .
H017 H 0.243824 0.792698 0.803244 0.033 Uiso 1 1 calc R . . . .
C018 C 0.4322(9) 0.6517(4) 0.9061(3) 0.0293(14) Uani 1 1 d . . . . .
H018 H 0.480445 0.615909 0.932275 0.035 Uiso 1 1 calc R . . . .
C019 C 0.2449(7) 0.6618(4) 0.7448(3) 0.0237(12) Uani 1 1 d . . . . .
H01C H 0.137463 0.641189 0.749882 0.028 Uiso 1 1 calc R . . . .
H01D H 0.236834 0.706558 0.718354 0.028 Uiso 1 1 calc R . . . .
C01A C 1.2219(9) 0.4884(5) 0.9510(4) 0.0363(17) Uani 1 1 d . . . . .
H01E H 1.303799 0.461866 0.971359 0.044 Uiso 1 1 calc R . . . .
C01B C 0.3474(10) 0.7756(5) 0.8882(4) 0.0392(18) Uani 1 1 d . . . . .
H01F H 0.338077 0.825390 0.902183 0.047 Uiso 1 1 calc R . . . .


_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
Br01 C00R 1.907(6) . ?
F004 C00O 1.330(7) . ?
F005 C00O 1.342(7) . ?
F006 C00O 1.346(7) . ?
O007 C00G 1.211(7) . ?
O008 C00D 1.220(8) . ?
O009 C00E 1.216(7) . ?
N00A C00D 1.337(8) . ?
N00A C00F 1.488(7) . ?
N00A C019 1.448(8) . ?
N00B C00G 1.367(7) . ?
N00B C010 1.413(8) . ?
N00B C011 1.454(8) . ?
N00C H00C 0.8800 . ?
N00C C00I 1.456(7) . ?
N00C C013 1.460(7) . ?
C00D C00E 1.528(8) . ?
C00E C00K 1.523(9) . ?
C00F H00A 0.9900 . ?
C00F H00B 0.9900 . ?
C00F C00K 1.538(8) . ?
C00G C013 1.557(8) . ?
C00H H00H 0.9500 . ?
C00H C00T 1.386(9) . ?
C00H C014 1.387(9) . ?
C00I H00I 1.0000 . ?
C00I C00M 1.539(8) . ?
C00I C00O 1.512(8) . ?
C00J H00J 0.9500 . ?
C00J C00X 1.366(9) . ?
C00J C00Y 1.400(9) . ?
C00K C00M 1.586(8) . ?
C00K C013 1.584(8) . ?
C00L C00M 1.520(8) . ?
C00L C00N 1.395(8) . ?
C00L C012 1.397(8) . ?
C00M H00M 1.0000 . ?
C00N H00N 0.9500 . ?
C00N C00U 1.393(9) . ?
C00P C00Z 1.392(9) . ?
C00P C017 1.390(9) . ?
C00P C019 1.530(8) . ?
C00Q H00Q 0.9500 . ?
C00Q C00V 1.403(10) . ?
C00Q C010 1.377(8) . ?
C00R C00S 1.388(9) . ?
C00R C00U 1.377(9) . ?
C00S H00S 0.9500 . ?
C00S C012 1.384(9) . ?
C00T C00W 1.395(9) . ?
C00T C011 1.514(9) . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C00Y 1.404(9) . ?
C00W H00W 0.9500 . ?
C00W C016 1.392(10) . ?
C00X C010 1.402(8) . ?
C00X C013 1.522(8) . ?
C00Y H00Y 0.9500 . ?
C00Z H00Z 0.9500 . ?
C00Z C018 1.394(9) . ?
C011 H01A 0.9900 . ?
C011 H01B 0.9900 . ?
C012 H012 0.9500 . ?
C014 H014 0.9500 . ?
C014 C01A 1.382(11) . ?
C015 H015 0.9500 . ?
C015 C018 1.371(11) . ?
C015 C01B 1.371(13) . ?
C016 H016 0.9500 . ?
C016 C01A 1.389(12) . ?
C017 H017 0.9500 . ?
C017 C01B 1.401(11) . ?
C018 H018 0.9500 . ?
C019 H01C 0.9900 . ?
C019 H01D 0.9900 . ?
C01A H01E 0.9500 . ?
C01B H01F 0.9500 . ?

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
C00D N00A C00F 115.5(5) . . ?
C00D N00A C019 123.8(5) . . ?
C019 N00A C00F 120.2(5) . . ?
C00G N00B C010 111.2(5) . . ?
C00G N00B C011 123.0(5) . . ?
C010 N00B C011 124.7(5) . . ?
C00I N00C H00C 126.7 . . ?
C00I N00C C013 106.6(4) . . ?
C013 N00C H00C 126.7 . . ?
O008 C00D N00A 128.1(6) . . ?
O008 C00D C00E 126.9(6) . . ?
N00A C00D C00E 105.0(5) . . ?
O009 C00E C00D 123.3(6) . . ?
O009 C00E C00K 127.3(6) . . ?
C00K C00E C00D 109.4(5) . . ?
N00A C00F H00A 110.8 . . ?
N00A C00F H00B 110.8 . . ?
N00A C00F C00K 104.7(5) . . ?
H00A C00F H00B 108.9 . . ?
C00K C00F H00A 110.8 . . ?
C00K C00F H00B 110.8 . . ?
O007 C00G N00B 127.0(5) . . ?
O007 C00G C013 125.0(5) . . ?
N00B C00G C013 108.0(5) . . ?
C00T C00H H00H 119.8 . . ?
C00T C00H C014 120.4(6) . . ?
C014 C00H H00H 119.8 . . ?
N00C C00I H00I 110.5 . . ?
N00C C00I C00M 103.0(5) . . ?
N00C C00I C00O 109.8(5) . . ?
C00M C00I H00I 110.5 . . ?
C00O C00I H00I 110.5 . . ?
C00O C00I C00M 112.3(5) . . ?
C00X C00J H00J 119.8 . . ?
C00X C00J C00Y 120.4(6) . . ?
C00Y C00J H00J 119.8 . . ?
C00E C00K C00F 102.0(5) . . ?
C00E C00K C00M 108.9(5) . . ?
C00E C00K C013 109.6(5) . . ?
C00F C00K C00M 118.5(5) . . ?
C00F C00K C013 114.3(5) . . ?
C013 C00K C00M 103.4(4) . . ?
C00N C00L C00M 123.5(5) . . ?
C00N C00L C012 118.6(5) . . ?
C012 C00L C00M 117.8(5) . . ?
C00I C00M C00K 104.4(4) . . ?
C00I C00M H00M 106.7 . . ?
C00K C00M H00M 106.7 . . ?
C00L C00M C00I 113.1(5) . . ?
C00L C00M C00K 118.6(5) . . ?
C00L C00M H00M 106.7 . . ?
C00L C00N H00N 119.7 . . ?
C00U C00N C00L 120.6(5) . . ?
C00U C00N H00N 119.7 . . ?
F004 C00O F005 107.3(5) . . ?
F004 C00O F006 106.6(5) . . ?
F004 C00O C00I 110.5(5) . . ?
F005 C00O F006 107.1(5) . . ?
F005 C00O C00I 111.2(5) . . ?
F006 C00O C00I 113.8(5) . . ?
C00Z C00P C019 120.9(6) . . ?
C017 C00P C00Z 119.5(6) . . ?
C017 C00P C019 119.6(6) . . ?
C00V C00Q H00Q 121.2 . . ?
C010 C00Q H00Q 121.2 . . ?
C010 C00Q C00V 117.7(6) . . ?
C00S C00R Br01 118.4(4) . . ?
C00U C00R Br01 119.9(5) . . ?
C00U C00R C00S 121.7(6) . . ?
C00R C00S H00S 120.7 . . ?
C012 C00S C00R 118.5(5) . . ?
C012 C00S H00S 120.7 . . ?
C00H C00T C00W 119.7(6) . . ?
C00H C00T C011 121.4(6) . . ?
C00W C00T C011 118.9(6) . . ?
C00N C00U H00U 120.4 . . ?
C00R C00U C00N 119.2(6) . . ?
C00R C00U H00U 120.4 . . ?
C00Q C00V H00V 119.8 . . ?
C00Q C00V C00Y 120.5(6) . . ?
C00Y C00V H00V 119.8 . . ?
C00T C00W H00W 120.0 . . ?
C016 C00W C00T 119.9(7) . . ?
C016 C00W H00W 120.0 . . ?
C00J C00X C010 119.1(6) . . ?
C00J C00X C013 132.7(6) . . ?
C010 C00X C013 108.0(5) . . ?
C00J C00Y C00V 119.7(6) . . ?
C00J C00Y H00Y 120.2 . . ?
C00V C00Y H00Y 120.2 . . ?
C00P C00Z H00Z 119.8 . . ?
C00P C00Z C018 120.4(6) . . ?
C018 C00Z H00Z 119.8 . . ?
C00Q C010 N00B 126.9(5) . . ?
C00Q C010 C00X 122.7(6) . . ?
C00X C010 N00B 110.4(5) . . ?
N00B C011 C00T 113.6(5) . . ?
N00B C011 H01A 108.8 . . ?
N00B C011 H01B 108.8 . . ?
C00T C011 H01A 108.8 . . ?
C00T C011 H01B 108.8 . . ?
H01A C011 H01B 107.7 . . ?
C00L C012 H012 119.3 . . ?
C00S C012 C00L 121.4(6) . . ?
C00S C012 H012 119.3 . . ?
N00C C013 C00G 111.5(5) . . ?
N00C C013 C00K 102.9(4) . . ?
N00C C013 C00X 111.6(5) . . ?
C00G C013 C00K 110.4(5) . . ?
C00X C013 C00G 102.3(4) . . ?
C00X C013 C00K 118.3(5) . . ?
C00H C014 H014 120.1 . . ?
C01A C014 C00H 119.9(7) . . ?
C01A C014 H014 120.1 . . ?
C018 C015 H015 119.8 . . ?
C01B C015 H015 119.8 . . ?
C01B C015 C018 120.5(7) . . ?
C00W C016 H016 120.2 . . ?
C01A C016 C00W 119.7(6) . . ?
C01A C016 H016 120.2 . . ?
C00P C017 H017 120.4 . . ?
C00P C017 C01B 119.1(7) . . ?
C01B C017 H017 120.4 . . ?
C00Z C018 H018 120.1 . . ?
C015 C018 C00Z 119.7(7) . . ?
C015 C018 H018 120.1 . . ?
N00A C019 C00P 112.4(5) . . ?
N00A C019 H01C 109.1 . . ?
N00A C019 H01D 109.1 . . ?
C00P C019 H01C 109.1 . . ?
C00P C019 H01D 109.1 . . ?
H01C C019 H01D 107.9 . . ?
C014 C01A C016 120.4(7) . . ?
C014 C01A H01E 119.8 . . ?
C016 C01A H01E 119.8 . . ?
C015 C01B C017 120.7(7) . . ?
C015 C01B H01F 119.6 . . ?
C017 C01B H01F 119.6 . . ?

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
Br01 C00R C00S C012 -179.8(5) . . . . ?
Br01 C00R C00U C00N -178.5(5) . . . . ?
O007 C00G C013 N00C 57.6(7) . . . . ?
O007 C00G C013 C00K -56.2(7) . . . . ?
O007 C00G C013 C00X 177.0(5) . . . . ?
O008 C00D C00E O009 9.3(10) . . . . ?
O008 C00D C00E C00K -172.3(6) . . . . ?
O009 C00E C00K C00F 161.3(6) . . . . ?
O009 C00E C00K C00M 35.2(8) . . . . ?
O009 C00E C00K C013 -77.2(7) . . . . ?
N00A C00D C00E O009 -168.8(6) . . . . ?
N00A C00D C00E C00K 9.6(6) . . . . ?
N00A C00F C00K C00E 17.6(6) . . . . ?
N00A C00F C00K C00M 137.1(5) . . . . ?
N00A C00F C00K C013 -100.5(5) . . . . ?
N00B C00G C013 N00C -120.7(5) . . . . ?
N00B C00G C013 C00K 125.6(5) . . . . ?
N00B C00G C013 C00X -1.2(6) . . . . ?
N00C C00I C00M C00K 29.0(6) . . . . ?
N00C C00I C00M C00L 159.4(5) . . . . ?
N00C C00I C00O F004 -177.4(5) . . . . ?
N00C C00I C00O F005 -58.4(7) . . . . ?
N00C C00I C00O F006 62.7(7) . . . . ?
C00D N00A C00F C00K -13.7(6) . . . . ?
C00D N00A C019 C00P 117.7(6) . . . . ?
C00D C00E C00K C00F -17.0(6) . . . . ?
C00D C00E C00K C00M -143.1(5) . . . . ?
C00D C00E C00K C013 104.5(5) . . . . ?
C00E C00K C00M C00I -121.1(5) . . . . ?
C00E C00K C00M C00L 111.9(6) . . . . ?
C00E C00K C013 N00C 94.8(5) . . . . ?
C00E C00K C013 C00G -146.1(5) . . . . ?
C00E C00K C013 C00X -28.8(7) . . . . ?
C00F N00A C00D O008 -175.3(6) . . . . ?
C00F N00A C00D C00E 2.8(6) . . . . ?
C00F N00A C019 C00P -70.8(7) . . . . ?
C00F C00K C00M C00I 123.1(5) . . . . ?
C00F C00K C00M C00L -3.9(8) . . . . ?
C00F C00K C013 N00C -151.5(5) . . . . ?
C00F C00K C013 C00G -32.4(7) . . . . ?
C00F C00K C013 C00X 84.9(6) . . . . ?
C00G N00B C010 C00Q 175.0(6) . . . . ?
C00G N00B C010 C00X -3.2(7) . . . . ?
C00G N00B C011 C00T -109.6(6) . . . . ?
C00H C00T C00W C016 2.1(10) . . . . ?
C00H C00T C011 N00B 28.1(9) . . . . ?
C00H C014 C01A C016 0.3(11) . . . . ?
C00I N00C C013 C00G -76.6(6) . . . . ?
C00I N00C C013 C00K 41.8(6) . . . . ?
C00I N00C C013 C00X 169.7(5) . . . . ?
C00J C00X C010 N00B 177.2(5) . . . . ?
C00J C00X C010 C00Q -1.1(9) . . . . ?
C00J C00X C013 N00C -55.4(9) . . . . ?
C00J C00X C013 C00G -174.7(7) . . . . ?
C00J C00X C013 C00K 63.8(9) . . . . ?
C00L C00N C00U C00R -1.3(9) . . . . ?
C00M C00I C00O F004 68.6(6) . . . . ?
C00M C00I C00O F005 -172.4(5) . . . . ?
C00M C00I C00O F006 -51.3(7) . . . . ?
C00M C00K C013 N00C -21.2(6) . . . . ?
C00M C00K C013 C00G 97.9(5) . . . . ?
C00M C00K C013 C00X -144.8(5) . . . . ?
C00M C00L C00N C00U 176.7(5) . . . . ?
C00M C00L C012 C00S -175.2(5) . . . . ?
C00N C00L C00M C00I -63.0(7) . . . . ?
C00N C00L C00M C00K 59.7(8) . . . . ?
C00N C00L C012 C00S 1.4(9) . . . . ?
C00O C00I C00M C00K 147.1(5) . . . . ?
C00O C00I C00M C00L -82.5(6) . . . . ?
C00P C00Z C018 C015 0.6(11) . . . . ?
C00P C017 C01B C015 -1.3(11) . . . . ?
C00Q C00V C00Y C00J -2.8(10) . . . . ?
C00R C00S C012 C00L -2.2(9) . . . . ?
C00S C00R C00U C00N 0.4(9) . . . . ?
C00T C00H C014 C01A -0.4(10) . . . . ?
C00T C00W C016 C01A -2.2(10) . . . . ?
C00U C00R C00S C012 1.3(9) . . . . ?
C00V C00Q C010 N00B -178.5(6) . . . . ?
C00V C00Q C010 C00X -0.5(9) . . . . ?
C00W C00T C011 N00B -153.0(6) . . . . ?
C00W C016 C01A C014 0.9(11) . . . . ?
C00X C00J C00Y C00V 1.3(10) . . . . ?
C00Y C00J C00X C010 0.6(9) . . . . ?
C00Y C00J C00X C013 174.2(6) . . . . ?
C00Z C00P C017 C01B 0.9(10) . . . . ?
C00Z C00P C019 N00A -38.3(8) . . . . ?
C010 N00B C00G O007 -175.5(6) . . . . ?
C010 N00B C00G C013 2.7(6) . . . . ?
C010 N00B C011 C00T 57.7(8) . . . . ?
C010 C00Q C00V C00Y 2.4(10) . . . . ?
C010 C00X C013 N00C 118.7(5) . . . . ?
C010 C00X C013 C00G -0.6(6) . . . . ?
C010 C00X C013 C00K -122.2(6) . . . . ?
C011 N00B C00G O007 -6.6(9) . . . . ?
C011 N00B C00G C013 171.5(5) . . . . ?
C011 N00B C010 C00Q 6.4(10) . . . . ?
C011 N00B C010 C00X -171.8(5) . . . . ?
C011 C00T C00W C016 -176.8(6) . . . . ?
C012 C00L C00M C00I 113.4(6) . . . . ?
C012 C00L C00M C00K -123.9(6) . . . . ?
C012 C00L C00N C00U 0.3(9) . . . . ?
C013 N00C C00I C00M -45.3(6) . . . . ?
C013 N00C C00I C00O -165.1(5) . . . . ?
C013 C00K C00M C00I -4.6(6) . . . . ?
C013 C00K C00M C00L -131.6(5) . . . . ?
C013 C00X C010 N00B 2.2(7) . . . . ?
C013 C00X C010 C00Q -176.1(6) . . . . ?
C014 C00H C00T C00W -0.9(10) . . . . ?
C014 C00H C00T C011 178.0(6) . . . . ?
C017 C00P C00Z C018 -0.5(10) . . . . ?
C017 C00P C019 N00A 144.6(6) . . . . ?
C018 C015 C01B C017 1.4(13) . . . . ?
C019 N00A C00D O008 -3.5(10) . . . . ?
C019 N00A C00D C00E 174.7(5) . . . . ?
C019 N00A C00F C00K 174.1(5) . . . . ?
C019 C00P C00Z C018 -177.6(6) . . . . ?
C019 C00P C017 C01B 178.0(6) . . . . ?
C01B C015 C018 C00Z -1.0(12) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.764 0.250 0.500 318.3 92.1 ?
2 0.286 0.750 0.000 318.3 91.1 ?

_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 2.865
_oxdiff_exptl_absorpt_empirical_full_min 0.441
####################################################################### 
# 
# 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_19010704
_database_code_depnum_ccdc_archive 'CCDC 1890458'
loop_
_audit_author_name
_audit_author_address
'Xiaoyun Zhao'
;Sun Yat-sen Univeisity
China
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2019-04-22 downloaded from the CCDC.
;
_audit_creation_date             2019-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C39 H30 F3 N3 O3, C H2 Cl2'
_chemical_formula_sum            'C40 H31 Cl2 F4 N2 O3'
_chemical_formula_weight         734.57
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     'ZXY-FN-13 Dn'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   11.9726(2)
_cell_length_b                   16.0021(3)
_cell_length_c                   18.2529(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3497.01(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9135
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.8590
_cell_measurement_theta_min      4.2700
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1516
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13408
_diffrn_reflns_theta_full        74.04
_diffrn_reflns_theta_max         74.04
_diffrn_reflns_theta_min         3.67
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  33.00   1.00    2.72    --  -41.14  38.00   0.00   94
  2  ω     -6.00  31.00   1.00    2.72    --  -41.14  38.00  30.00   37
  3  ω     55.00  96.00   1.00    2.72    --   41.14-125.00   0.00   41
  4  ω     40.00  69.00   1.00    2.72    --   41.14-125.00 -90.00   29
  5  ω     51.00 110.00   1.00   10.00    --  107.79 -94.00 120.00   59
  6  ω     51.00 106.00   1.00   10.00    --  107.79-125.00 120.00   55
  7  ω     35.00  60.00   1.00   10.00    --  107.79 -45.00 120.00   25
  8  ω     32.00 101.00   1.00   10.00    --  107.79 -30.00   0.00   69
  9  ω     55.00 178.00   1.00   10.00    --  107.79  15.00 -60.00  123
 10  ω     82.00 178.00   1.00   10.00    --  107.79  30.00   0.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0492744000
_diffrn_orient_matrix_UB_12      -0.0888831000
_diffrn_orient_matrix_UB_13      -0.0010571000
_diffrn_orient_matrix_UB_21      -0.0536561000
_diffrn_orient_matrix_UB_22      0.0154693000
_diffrn_orient_matrix_UB_23      0.0755909000
_diffrn_orient_matrix_UB_31      -0.1059794000
_diffrn_orient_matrix_UB_32      0.0334896000
_diffrn_orient_matrix_UB_33      -0.0377074000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6517
_reflns_number_total             6886
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-1997 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         6886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0809P)²+1.4323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1448
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B), C27(H27A,H27B), C49(H49A,H49B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C23(H23), C24(H24),
 C25(H25), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C40(H40),
  C41(H41), C42(H42), C44(H44), C45(H45), C46(H46), C47(H47)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.86056(19) 0.30631(14) 0.63193(14) 0.0260(5) Uani 1 d . . .
C2 C 0.87573(19) 0.32451(14) 0.54814(14) 0.0256(5) Uani 1 d . . .
C3 C 0.83840(19) 0.41828(14) 0.54571(13) 0.0246(4) Uani 1 d . . .
H3 H 0.8950 0.4512 0.5717 0.030 Uiso 1 calc . . R
C4 C 0.73376(19) 0.41380(15) 0.59503(13) 0.0254(4) Uani 1 d . . .
H4 H 0.6703 0.3943 0.5658 0.030 Uiso 1 calc . . R
C6 C 0.80311(19) 0.26896(15) 0.49814(13) 0.0265(5) Uani 1 d . . .
H6A H 0.7698 0.2237 0.5260 0.032 Uiso 1 calc . . R
H6B H 0.7440 0.3015 0.4757 0.032 Uiso 1 calc . . R
C8 C 0.9859(2) 0.25797(15) 0.45022(14) 0.0280(5) Uani 1 d . . .
C9 C 0.99378(19) 0.30910(14) 0.51961(14) 0.0254(5) Uani 1 d . . .
C12 C 0.8390(2) 0.17878(16) 0.38650(14) 0.0314(5) Uani 1 d . . .
H12A H 0.8871 0.1832 0.3439 0.038 Uiso 1 calc . . R
H12B H 0.7645 0.1956 0.3717 0.038 Uiso 1 calc . . R
C13 C 0.8356(2) 0.08859(17) 0.41083(15) 0.0335(5) Uani 1 d . . .
C14 C 0.7595(3) 0.0349(2) 0.3766(2) 0.0485(7) Uani 1 d . . .
H14 H 0.7090 0.0559 0.3425 0.058 Uiso 1 calc . . R
C15 C 0.7597(4) -0.0494(2) 0.3935(3) 0.0674(11) Uani 1 d . . .
H15 H 0.7096 -0.0851 0.3704 0.081 Uiso 1 calc . . R
C16 C 0.8340(4) -0.0809(2) 0.4446(2) 0.0614(9) Uani 1 d . . .
H16 H 0.8343 -0.1377 0.4554 0.074 Uiso 1 calc . . R
C17 C 0.9078(3) -0.0277(2) 0.4794(2) 0.0506(8) Uani 1 d . . .
H17 H 0.9574 -0.0485 0.5142 0.061 Uiso 1 calc . . R
C18 C 0.9078(2) 0.0569(2) 0.46247(17) 0.0407(6) Uani 1 d . . .
H18 H 0.9572 0.0926 0.4863 0.049 Uiso 1 calc . . R
C19 C 0.8626(2) 0.21541(15) 0.65542(14) 0.0299(5) Uani 1 d . . .
C20 C 0.9549(2) 0.20228(16) 0.70040(15) 0.0323(5) Uani 1 d . . .
C22 C 0.9606(2) 0.34274(15) 0.67706(14) 0.0280(5) Uani 1 d . . .
C23 C 0.7902(2) 0.14957(16) 0.64198(16) 0.0359(6) Uani 1 d . . .
H23 H 0.7266 0.1574 0.6135 0.043 Uiso 1 calc . . R
C24 C 0.8141(3) 0.07165(17) 0.67184(18) 0.0439(7) Uani 1 d . . .
H24 H 0.7664 0.0270 0.6628 0.053 Uiso 1 calc . . R
C25 C 0.9079(3) 0.05975(17) 0.71486(18) 0.0451(7) Uani 1 d . . .
H25 H 0.9231 0.0069 0.7334 0.054 Uiso 1 calc . . R
C26 C 0.9796(3) 0.12534(18) 0.73076(17) 0.0414(6) Uani 1 d . . .
H26 H 1.0418 0.1179 0.7606 0.050 Uiso 1 calc . . R
C27 C 1.0985(2) 0.28847(18) 0.76773(16) 0.0368(6) Uani 1 d . . .
H27A H 1.1289 0.3445 0.7642 0.044 Uiso 1 calc . . R
H27B H 1.1587 0.2493 0.7583 0.044 Uiso 1 calc . . R
C28 C 1.0546(3) 0.27458(18) 0.84437(17) 0.0408(6) Uani 1 d . . .
C29 C 1.1147(4) 0.2278(2) 0.8947(2) 0.0573(9) Uani 1 d . . .
H29 H 1.1830 0.2045 0.8814 0.069 Uiso 1 calc . . R
C30 C 1.0729(6) 0.2156(3) 0.9649(2) 0.0808(16) Uani 1 d . . .
H30 H 1.1134 0.1840 0.9984 0.097 Uiso 1 calc . . R
C31 C 0.9713(6) 0.2501(3) 0.9855(2) 0.0881(18) Uani 1 d . . .
H31 H 0.9435 0.2415 1.0325 0.106 Uiso 1 calc . . R
C32 C 0.9122(5) 0.2969(3) 0.9360(3) 0.0788(13) Uani 1 d . . .
H32 H 0.8445 0.3208 0.9497 0.095 Uiso 1 calc . . R
C33 C 0.9528(3) 0.3088(2) 0.8661(2) 0.0546(8) Uani 1 d . . .
H33 H 0.9115 0.3403 0.8329 0.065 Uiso 1 calc . . R
C35 C 0.7048(2) 0.49730(16) 0.62898(14) 0.0303(5) Uani 1 d . . .
C39 C 0.8226(2) 0.45717(16) 0.47054(14) 0.0307(5) Uani 1 d . . .
C40 C 0.7207(2) 0.45588(19) 0.43525(15) 0.0376(6) Uani 1 d . . .
H40 H 0.6611 0.4284 0.4573 0.045 Uiso 1 calc . . R
C41 C 0.7039(3) 0.4951(2) 0.36656(16) 0.0462(7) Uani 1 d . . .
H41 H 0.6342 0.4929 0.3441 0.055 Uiso 1 calc . . R
C42 C 0.7890(3) 0.5357(2) 0.33372(16) 0.0480(8) Uani 1 d . . .
H42 H 0.7770 0.5627 0.2893 0.058 Uiso 1 calc . . R
C43 C 0.8959(3) 0.53763(18) 0.36616(16) 0.0401(6) Uani 1 d . . .
C44 C 0.9857(3) 0.5797(2) 0.33123(18) 0.0518(8) Uani 1 d . . .
H44 H 0.9740 0.6051 0.2860 0.062 Uiso 1 calc . . R
C45 C 1.0893(3) 0.5838(2) 0.3628(2) 0.0536(8) Uani 1 d . . .
H45 H 1.1476 0.6110 0.3390 0.064 Uiso 1 calc . . R
C46 C 1.1065(3) 0.5466(2) 0.4310(2) 0.0472(7) Uani 1 d . . .
H46 H 1.1769 0.5497 0.4525 0.057 Uiso 1 calc . . R
C47 C 1.0228(2) 0.50593(18) 0.46704(16) 0.0382(6) Uani 1 d . . .
H47 H 1.0371 0.4822 0.5126 0.046 Uiso 1 calc . . R
C48 C 0.9136(2) 0.49918(16) 0.43590(14) 0.0327(5) Uani 1 d . . .
F36 F 0.61352(13) 0.49022(10) 0.67134(9) 0.0384(4) Uani 1 d . . .
F37 F 0.78601(14) 0.52872(10) 0.67099(9) 0.0394(4) Uani 1 d . . .
F38 F 0.68100(16) 0.55534(10) 0.57826(9) 0.0434(4) Uani 1 d . . .
N5 N 0.75821(17) 0.35190(13) 0.65181(11) 0.0261(4) Uani 1 d . . .
H5 H 0.707(3) 0.314(2) 0.6556(18) 0.031 Uiso 1 d . . R
N7 N 0.87888(17) 0.23623(13) 0.44248(12) 0.0274(4) Uani 1 d . . .
N21 N 1.01213(18) 0.27782(14) 0.71218(13) 0.0321(5) Uani 1 d . . .
O10 O 1.08060(14) 0.32765(13) 0.54815(13) 0.0405(5) Uani 1 d . . .
O11 O 1.06533(17) 0.23887(15) 0.41096(12) 0.0460(5) Uani 1 d . . .
O34 O 0.98560(16) 0.41570(11) 0.68297(10) 0.0334(4) Uani 1 d . . .
C49 C 0.4613(4) 0.6447(3) 0.7345(4) 0.098(2) Uani 1 d A 1 .
H49A H 0.4399 0.6239 0.7824 0.118 Uiso 1 calc A 1 R
H49B H 0.4572 0.5986 0.7002 0.118 Uiso 1 calc A 1 R
Cl50 Cl 0.36593(12) 0.72447(6) 0.70703(8) 0.0832(4) Uani 1 d A 1 .
Cl51 Cl 0.59662(13) 0.68100(13) 0.73818(18) 0.1850(15) Uani 1 d A 1 .


_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
C1 C2 1.568(3) . ?
C1 C19 1.517(3) . ?
C1 C22 1.567(3) . ?
C1 N5 1.471(3) . ?
C2 C3 1.566(3) . ?
C2 C6 1.542(3) . ?
C2 C9 1.526(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.544(3) . ?
C3 C39 1.518(3) . ?
C4 H4 0.9800 . ?
C4 C35 1.513(3) . ?
C4 N5 1.463(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N7 1.459(3) . ?
C8 C9 1.511(3) . ?
C8 N7 1.335(3) . ?
C8 O11 1.229(3) . ?
C9 O10 1.200(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.511(4) . ?
C12 N7 1.455(3) . ?
C13 C14 1.399(4) . ?
C13 C18 1.376(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(4) . ?
C19 C23 1.386(4) . ?
C20 C26 1.382(4) . ?
C20 N21 1.406(3) . ?
C22 N21 1.368(3) . ?
C22 O34 1.210(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.391(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.387(4) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.511(4) . ?
C27 N21 1.458(3) . ?
C28 C29 1.387(5) . ?
C28 C33 1.395(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.390(7) . ?
C30 H30 0.9300 . ?
C30 C31 1.388(9) . ?
C31 H31 0.9300 . ?
C31 C32 1.371(8) . ?
C32 H32 0.9300 . ?
C32 C33 1.378(6) . ?
C33 H33 0.9300 . ?
C35 F36 1.344(3) . ?
C35 F37 1.336(3) . ?
C35 F38 1.342(3) . ?
C39 C40 1.379(4) . ?
C39 C48 1.428(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.416(4) . ?
C41 H41 0.9300 . ?
C41 C42 1.349(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.411(5) . ?
C43 C44 1.420(5) . ?
C43 C48 1.429(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.369(6) . ?
C45 H45 0.9300 . ?
C45 C46 1.394(5) . ?
C46 H46 0.9300 . ?
C46 C47 1.364(4) . ?
C47 H47 0.9300 . ?
C47 C48 1.431(4) . ?
N5 H5 0.86(4) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C49 Cl50 1.785(6) . ?
C49 Cl51 1.722(5) . ?

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
C19 C1 C2 116.9(2) . . ?
C19 C1 C22 101.31(19) . . ?
C22 C1 C2 110.81(19) . . ?
N5 C1 C2 104.18(18) . . ?
N5 C1 C19 114.8(2) . . ?
N5 C1 C22 108.83(19) . . ?
C3 C2 C1 99.93(18) . . ?
C6 C2 C1 113.88(19) . . ?
C6 C2 C3 112.00(19) . . ?
C9 C2 C1 114.21(19) . . ?
C9 C2 C3 114.17(19) . . ?
C9 C2 C6 103.12(18) . . ?
C2 C3 H3 107.7 . . ?
C4 C3 C2 99.81(18) . . ?
C4 C3 H3 107.7 . . ?
C39 C3 C2 117.0(2) . . ?
C39 C3 H3 107.7 . . ?
C39 C3 C4 116.40(19) . . ?
C3 C4 H4 109.0 . . ?
C35 C4 C3 112.5(2) . . ?
C35 C4 H4 109.0 . . ?
N5 C4 C3 106.39(18) . . ?
N5 C4 H4 109.0 . . ?
N5 C4 C35 110.7(2) . . ?
C2 C6 H6A 110.6 . . ?
C2 C6 H6B 110.6 . . ?
H6A C6 H6B 108.8 . . ?
N7 C6 C2 105.56(19) . . ?
N7 C6 H6A 110.6 . . ?
N7 C6 H6B 110.6 . . ?
N7 C8 C9 106.8(2) . . ?
O11 C8 C9 125.1(2) . . ?
O11 C8 N7 128.0(2) . . ?
C8 C9 C2 108.42(19) . . ?
O10 C9 C2 127.9(2) . . ?
O10 C9 C8 123.5(2) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
N7 C12 H12A 108.8 . . ?
N7 C12 H12B 108.8 . . ?
N7 C12 C13 114.0(2) . . ?
C14 C13 C12 118.2(3) . . ?
C18 C13 C12 122.4(2) . . ?
C18 C13 C14 119.3(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 120.8(3) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C1 108.9(2) . . ?
C23 C19 C1 132.0(2) . . ?
C23 C19 C20 119.1(2) . . ?
C19 C20 N21 110.3(2) . . ?
C26 C20 C19 122.7(3) . . ?
C26 C20 N21 126.9(2) . . ?
N21 C22 C1 108.0(2) . . ?
O34 C22 C1 126.5(2) . . ?
O34 C22 N21 125.4(2) . . ?
C19 C23 H23 120.6 . . ?
C19 C23 C24 118.9(3) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.9(3) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.2(3) . . ?
C26 C25 H25 119.4 . . ?
C20 C26 C25 117.2(3) . . ?
C20 C26 H26 121.4 . . ?
C25 C26 H26 121.4 . . ?
H27A C27 H27B 107.9 . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
N21 C27 H27A 109.1 . . ?
N21 C27 H27B 109.1 . . ?
N21 C27 C28 112.3(2) . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 C33 118.5(3) . . ?
C33 C28 C27 120.7(3) . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.0(5) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.7 . . ?
C31 C30 C29 120.7(4) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.4(4) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.3(5) . . ?
C33 C32 H32 119.9 . . ?
C28 C33 H33 119.4 . . ?
C32 C33 C28 121.1(4) . . ?
C32 C33 H33 119.4 . . ?
F36 C35 C4 110.3(2) . . ?
F37 C35 C4 113.6(2) . . ?
F37 C35 F36 107.1(2) . . ?
F37 C35 F38 106.9(2) . . ?
F38 C35 C4 112.2(2) . . ?
F38 C35 F36 106.4(2) . . ?
C40 C39 C3 121.7(2) . . ?
C40 C39 C48 118.3(2) . . ?
C48 C39 C3 119.9(2) . . ?
C39 C40 H40 118.9 . . ?
C39 C40 C41 122.2(3) . . ?
C41 C40 H40 118.9 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.0(3) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 119.7 . . ?
C41 C42 C43 120.6(3) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 C44 120.6(3) . . ?
C42 C43 C48 119.9(3) . . ?
C44 C43 C48 119.5(3) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 C43 121.3(3) . . ?
C45 C44 H44 119.4 . . ?
C44 C45 H45 120.3 . . ?
C44 C45 C46 119.3(3) . . ?
C46 C45 H45 120.3 . . ?
C45 C46 H46 119.2 . . ?
C47 C46 C45 121.7(3) . . ?
C47 C46 H46 119.2 . . ?
C46 C47 H47 119.5 . . ?
C46 C47 C48 121.1(3) . . ?
C48 C47 H47 119.5 . . ?
C39 C48 C43 119.0(2) . . ?
C39 C48 C47 123.9(2) . . ?
C43 C48 C47 117.2(3) . . ?
C1 N5 H5 106(2) . . ?
C4 N5 C1 109.12(19) . . ?
C4 N5 H5 113(2) . . ?
C8 N7 C6 115.4(2) . . ?
C8 N7 C12 123.6(2) . . ?
C12 N7 C6 120.8(2) . . ?
C20 N21 C27 123.5(2) . . ?
C22 N21 C20 111.2(2) . . ?
C22 N21 C27 123.8(2) . . ?
H49A C49 H49B 107.9 . . ?
Cl50 C49 H49A 109.3 . . ?
Cl50 C49 H49B 109.3 . . ?
Cl51 C49 H49A 109.3 . . ?
Cl51 C49 H49B 109.3 . . ?
Cl51 C49 Cl50 111.8(3) . . ?


_olex2_date_sample_data_collection 2019-01-07
_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 1.522
_oxdiff_exptl_absorpt_empirical_full_min 0.684
