# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_h8a1
_database_code_depnum_ccdc_archive 'CCDC 1868292'
_audit_update_record             
;
2018-09-18 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H11 F12 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         579.37

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   35.48(3)
_cell_length_b                   14.931(11)
_cell_length_c                   8.852(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.42(2)
_cell_angle_gamma                90
_cell_volume                     4626.(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    788
_cell_measurement_theta_min      2.3508
_cell_measurement_theta_max      20.1220
_cell_measurement_temperature    103.0(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.032
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2312

_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.0(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            20383
_diffrn_reflns_av_R_equivalents  0.2320
_diffrn_reflns_av_unetI/netI     0.1944
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             3322
_reflns_number_gt                1850
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1687
_refine_ls_R_factor_gt           0.0988
_refine_ls_wR_factor_gt          0.2209
_refine_ls_wR_factor_ref         0.2659
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         3322
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0955P)²+0.8479P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.363
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       ?
_computing_cell_refinement       'APEX3 v2017.7-RC3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 853)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F001 0.70714(13) 0.8249(3) 0.2389(5) 0.0588(14) Uani d . . . 1 . .
F F002 0.67852(13) 0.8932(3) 0.0414(5) 0.0583(14) Uani d . . . 1 . .
F F003 0.58685(14) 1.0622(3) 0.4563(5) 0.0574(14) Uani d . . . 1 . .
F F004 0.66642(14) 0.6916(3) 0.8625(5) 0.0643(15) Uani d . . . 1 . .
F F005 0.69729(14) 0.9652(3) 0.2495(5) 0.0633(15) Uani d . . . 1 . .
F F006 0.63950(16) 0.7990(4) 0.7325(5) 0.0721(16) Uani d . . . 1 . .
F F007 0.70065(15) 0.7850(4) 0.7644(5) 0.0740(17) Uani d . . . 1 . .
F F008 0.56798(16) 0.9544(3) 0.5872(5) 0.0673(15) Uani d . . . 1 . .
F F009 0.53395(15) 0.9937(3) 0.3759(6) 0.0697(16) Uani d . . . 1 . .
F F00A 0.72896(14) 0.5718(4) 0.2201(5) 0.0693(16) Uani d . . . 1 . .
F F00B 0.76155(14) 0.5882(4) 0.4430(6) 0.0741(17) Uani d . . . 1 . .
F F00C 0.72980(15) 0.4686(4) 0.3842(6) 0.0748(16) Uani d . . . 1 . .
N N1 0.54545(17) 0.4839(4) 0.1499(6) 0.0341(15) Uani d . . . 1 . .
N N2 0.48770(18) 0.3748(4) -0.0326(6) 0.0328(15) Uani d . . . 1 . .
C C00F 0.5759(2) 0.5153(5) 0.2544(8) 0.0297(17) Uani d . . . 1 . .
C C00G 0.4795(2) 0.2247(5) -0.0232(7) 0.0309(18) Uani d . . . 1 . .
H H00G 0.469157 0.166478 -0.044245 0.037 Uiso calc U . R 1 . .
C C00H 0.57029(19) 0.6836(5) 0.2000(7) 0.0287(17) Uani d . . . 1 . .
C C00I 0.5159(2) 0.3398(5) 0.0753(8) 0.0336(18) Uani d . . . 1 . .
C C00J 0.6258(2) 0.7895(5) 0.1986(7) 0.0333(18) Uani d . . . 1 . .
H H00J 0.637768 0.747418 0.141594 0.04 Uiso calc U . R 1 . .
C C00K 0.5877(2) 0.6050(5) 0.2688(7) 0.0291(17) Uani d . . . 1 . .
C C00L 0.5901(2) 0.7694(5) 0.2393(7) 0.0315(18) Uani d . . . 1 . .
C C00M 0.5436(2) 0.3942(5) 0.1646(7) 0.0309(17) Uani d . . . 1 . .
C C00N 0.5728(2) 0.8352(5) 0.3216(7) 0.0355(19) Uani d . . . 1 . .
H H00N 0.548569 0.823791 0.350134 0.043 Uiso calc U . R 1 . .
C C00O 0.4645(2) 0.3072(5) -0.0930(8) 0.0319(18) Uani d . . . 1 . .
C C00P 0.5934(2) 0.4395(4) 0.3386(7) 0.0314(18) Uani d . . . 1 . .
H H00P 0.615018 0.441173 0.417776 0.038 Uiso calc U . R 1 . .
C C00Q 0.5737(2) 0.3660(5) 0.2850(7) 0.0332(19) Uani d . . . 1 . .
H H00Q 0.578781 0.306365 0.320011 0.04 Uiso calc U . R 1 . .
C C00R 0.5109(2) 0.2460(5) 0.0779(8) 0.0367(19) Uani d . . . 1 . .
H H00R 0.526944 0.204857 0.140288 0.044 Uiso calc U . R 1 . .
C C00S 0.6821(2) 0.8882(6) 0.1953(9) 0.044(2) Uani d . . . 1 . .
C C00T 0.6588(2) 0.5817(5) 0.3337(8) 0.0354(19) Uani d . . . 1 . .
H H00T 0.657035 0.546128 0.243839 0.043 Uiso calc U . R 1 . .
C C00U 0.5908(2) 0.9146(5) 0.3596(8) 0.0363(19) Uani d . . . 1 . .
C C00V 0.6253(2) 0.6165(5) 0.3740(7) 0.0326(18) Uani d . . . 1 . .
C C00W 0.6942(2) 0.5967(5) 0.4186(8) 0.0365(19) Uani d . . . 1 . .
C C00X 0.6645(2) 0.6836(5) 0.5961(8) 0.0365(19) Uani d . . . 1 . .
C C00Y 0.5700(2) 0.9825(5) 0.4430(9) 0.045(2) Uani d . . . 1 . .
C C00Z 0.6436(2) 0.8704(5) 0.2410(8) 0.0353(18) Uani d . . . 1 . .
C C010 0.6289(2) 0.6690(5) 0.5066(8) 0.0355(19) Uani d . . . 1 . .
H H010 0.60674 0.694923 0.536045 0.043 Uiso calc U . R 1 . .
C C011 0.7288(2) 0.5570(6) 0.3697(9) 0.045(2) Uani d . . . 1 . .
C C012 0.6681(3) 0.7401(6) 0.7391(8) 0.045(2) Uani d . . . 1 . .
C C013 0.6267(2) 0.9334(5) 0.3239(8) 0.041(2) Uani d . . . 1 . .
H H013 0.639293 0.988048 0.355416 0.049 Uiso calc U . R 1 . .
C C014 0.6974(2) 0.6485(5) 0.5513(8) 0.042(2) Uani d . . . 1 . .
H H014 0.721795 0.659766 0.610588 0.051 Uiso calc U . R 1 . .
H H1N 0.4777(19) 0.434(5) -0.080(8) 0.04(2) Uiso d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F001 C00S . 1.312(9) ?
F002 C00S . 1.349(8) ?
F003 C00Y . 1.328(8) ?
F004 C012 . 1.320(8) ?
F005 C00S . 1.326(9) ?
F006 C012 . 1.339(10) ?
F007 C012 . 1.321(9) ?
F008 C00Y . 1.357(9) ?
F009 C00Y . 1.331(9) ?
F00A C011 . 1.342(8) ?
F00B C011 . 1.319(9) ?
F00C C011 . 1.327(10) ?
N1 C00M . 1.349(9) ?
N1 C00F . 1.383(9) ?
N2 C00O . 1.357(8) ?
N2 C00I . 1.369(9) ?
N2 H1N . 1.01(8) ?
C00F C00K . 1.403(9) ?
C00F C00P . 1.439(9) ?
C00G C00R . 1.349(10) ?
C00G C00O . 1.439(10) ?
C00G H00G . 0.95 ?
C00H C00K . 1.416(9) ?
C00H C00O 5_665 1.434(10) ?
C00H C00L . 1.476(9) ?
C00I C00M . 1.412(10) ?
C00I C00R . 1.413(10) ?
C00J C00Z . 1.386(10) ?
C00J C00L . 1.402(10) ?
C00J H00J . 0.95 ?
C00K C00V . 1.508(10) ?
C00L C00N . 1.421(9) ?
C00M C00Q . 1.444(9) ?
C00N C00U . 1.363(10) ?
C00N H00N . 0.95 ?
C00P C00Q . 1.346(9) ?
C00P H00P . 0.95 ?
C00Q H00Q . 0.95 ?
C00R H00R . 0.95 ?
C00S C00Z . 1.510(11) ?
C00T C00W . 1.373(10) ?
C00T C00V . 1.396(10) ?
C00T H00T . 0.95 ?
C00U C013 . 1.388(10) ?
C00U C00Y . 1.515(10) ?
C00V C010 . 1.399(10) ?
C00W C014 . 1.395(10) ?
C00W C011 . 1.489(11) ?
C00X C010 . 1.393(10) ?
C00X C014 . 1.398(10) ?
C00X C012 . 1.508(10) ?
C00Z C013 . 1.389(10) ?
C010 H010 . 0.95 ?
C013 H013 . 0.95 ?
C014 H014 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C00M N1 C00F . . 108.5(6) ?
C00O N2 C00I . . 108.5(6) ?
C00O N2 H1N . . 110.(4) ?
C00I N2 H1N . . 142.(4) ?
N1 C00F C00K . . 125.0(6) ?
N1 C00F C00P . . 107.7(6) ?
C00K C00F C00P . . 127.3(6) ?
C00R C00G C00O . . 106.9(6) ?
C00R C00G H00G . . 126.5 ?
C00O C00G H00G . . 126.5 ?
C00K C00H C00O . 5_665 129.1(6) ?
C00K C00H C00L . . 117.4(6) ?
C00O C00H C00L 5_665 . 113.5(6) ?
N2 C00I C00M . . 122.2(7) ?
N2 C00I C00R . . 108.1(7) ?
C00M C00I C00R . . 129.7(7) ?
C00Z C00J C00L . . 120.5(6) ?
C00Z C00J H00J . . 119.7 ?
C00L C00J H00J . . 119.7 ?
C00F C00K C00H . . 130.5(6) ?
C00F C00K C00V . . 112.7(6) ?
C00H C00K C00V . . 116.8(6) ?
C00J C00L C00N . . 117.9(7) ?
C00J C00L C00H . . 122.7(6) ?
C00N C00L C00H . . 119.4(6) ?
N1 C00M C00I . . 123.9(7) ?
N1 C00M C00Q . . 108.6(6) ?
C00I C00M C00Q . . 127.5(7) ?
C00U C00N C00L . . 120.2(7) ?
C00U C00N H00N . . 119.9 ?
C00L C00N H00N . . 119.9 ?
N2 C00O C00H . 5_665 126.1(6) ?
N2 C00O C00G . . 108.1(6) ?
C00H C00O C00G 5_665 . 125.7(6) ?
C00Q C00P C00F . . 107.6(6) ?
C00Q C00P H00P . . 126.2 ?
C00F C00P H00P . . 126.2 ?
C00P C00Q C00M . . 107.6(6) ?
C00P C00Q H00Q . . 126.2 ?
C00M C00Q H00Q . . 126.2 ?
C00G C00R C00I . . 108.3(7) ?
C00G C00R H00R . . 125.8 ?
C00I C00R H00R . . 125.8 ?
F001 C00S F005 . . 107.6(7) ?
F001 C00S F002 . . 106.5(6) ?
F005 C00S F002 . . 106.5(6) ?
F001 C00S C00Z . . 113.2(7) ?
F005 C00S C00Z . . 112.8(6) ?
F002 C00S C00Z . . 109.9(7) ?
C00W C00T C00V . . 122.7(7) ?
C00W C00T H00T . . 118.6 ?
C00V C00T H00T . . 118.6 ?
C00N C00U C013 . . 122.0(7) ?
C00N C00U C00Y . . 117.1(7) ?
C013 C00U C00Y . . 120.8(7) ?
C00T C00V C010 . . 117.3(7) ?
C00T C00V C00K . . 120.3(6) ?
C010 C00V C00K . . 122.1(6) ?
C00T C00W C014 . . 119.5(7) ?
C00T C00W C011 . . 119.9(7) ?
C014 C00W C011 . . 120.6(7) ?
C010 C00X C014 . . 120.1(7) ?
C010 C00X C012 . . 120.7(7) ?
C014 C00X C012 . . 119.1(7) ?
F003 C00Y F009 . . 108.2(7) ?
F003 C00Y F008 . . 106.6(6) ?
F009 C00Y F008 . . 105.2(7) ?
F003 C00Y C00U . . 113.3(7) ?
F009 C00Y C00U . . 112.1(6) ?
F008 C00Y C00U . . 110.9(7) ?
C00J C00Z C013 . . 121.0(7) ?
C00J C00Z C00S . . 118.3(7) ?
C013 C00Z C00S . . 120.7(7) ?
C00X C010 C00V . . 120.9(7) ?
C00X C010 H010 . . 119.5 ?
C00V C010 H010 . . 119.5 ?
F00B C011 F00C . . 107.2(7) ?
F00B C011 F00A . . 106.4(7) ?
F00C C011 F00A . . 104.7(7) ?
F00B C011 C00W . . 114.7(7) ?
F00C C011 C00W . . 112.2(7) ?
F00A C011 C00W . . 111.0(7) ?
F004 C012 F007 . . 107.2(6) ?
F004 C012 F006 . . 105.0(6) ?
F007 C012 F006 . . 108.0(7) ?
F004 C012 C00X . . 112.2(7) ?
F007 C012 C00X . . 112.3(6) ?
F006 C012 C00X . . 111.7(7) ?
C00U C013 C00Z . . 118.3(7) ?
C00U C013 H013 . . 120.8 ?
C00Z C013 H013 . . 120.8 ?
C00W C014 C00X . . 119.4(7) ?
C00W C014 H014 . . 120.3 ?
C00X C014 H014 . . 120.3 ?



####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1868296'
_audit_update_record             
;
2018-09-18 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H32 Cl6 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         853.45

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.235(16)
_cell_length_b                   9.638(17)
_cell_length_c                   11.86(2)
_cell_angle_alpha                78.93(3)
_cell_angle_beta                 76.86(5)
_cell_angle_gamma                73.21(4)
_cell_volume                     975.(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1645
_cell_measurement_theta_min      2.3428
_cell_measurement_theta_max      28.7230
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             438

_exptl_absorpt_coefficient_mu    0.481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            6705
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             4940
_reflns_number_gt                3454
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1604
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_number_reflns         4940
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.550
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7009(3) 0.2041(3) 0.3967(2) 0.0136(5) Uani d . . . 1 . .
C C2 0.8586(3) 0.1370(3) 0.4088(2) 0.0166(6) Uani d . . . 1 . .
H H2 0.9224 0.0508 0.3783 0.02 Uiso calc U . R 1 . .
C C3 0.9002(3) 0.2190(3) 0.4716(2) 0.0164(6) Uani d . . . 1 . .
H H3 0.9979 0.2008 0.4929 0.02 Uiso calc U . R 1 . .
C C4 0.7689(3) 0.3378(3) 0.4994(2) 0.0146(5) Uani d . . . 1 . .
C C5 0.7542(3) 0.4523(3) 0.5624(2) 0.0135(5) Uani d . . . 1 . .
C C6 0.8676(3) 0.4748(3) 0.6165(2) 0.0171(6) Uani d . . . 1 . .
H H6 0.9689 0.4142 0.6176 0.021 Uiso calc U . R 1 . .
C C7 0.8024(3) 0.5993(3) 0.6660(2) 0.0183(6) Uani d . . . 1 . .
H H7 0.8498 0.6423 0.7085 0.022 Uiso calc U . R 1 . .
C C8 0.6478(3) 0.6548(3) 0.6424(2) 0.0141(5) Uani d . . . 1 . .
C C9 0.5408(3) 0.7830(3) 0.6799(2) 0.0150(5) Uani d . . . 1 . .
C C10 0.3889(3) 0.8454(3) 0.6621(2) 0.0150(5) Uani d . . . 1 . .
C C11 0.6041(3) 0.8595(3) 0.7493(2) 0.0148(5) Uani d . . . 1 . .
C C12 0.5872(3) 0.8215(3) 0.8710(2) 0.0201(6) Uani d . . . 1 . .
H H12 0.5321 0.751 0.9092 0.024 Uiso calc U . R 1 . .
C C13 0.6507(4) 0.8863(3) 0.9361(3) 0.0237(6) Uani d . . . 1 . .
H H13 0.6407 0.8585 1.0182 0.028 Uiso calc U . R 1 . .
C C14 0.7285(4) 0.9914(3) 0.8815(3) 0.0240(6) Uani d . . . 1 . .
H H14 0.7706 1.0367 0.9261 0.029 Uiso calc U . R 1 . .
C C15 0.7448(4) 1.0302(3) 0.7610(3) 0.0246(6) Uani d . . . 1 . .
H H15 0.7982 1.1022 0.7233 0.03 Uiso calc U . R 1 . .
C C16 0.6834(3) 0.9645(3) 0.6961(3) 0.0212(6) Uani d . . . 1 . .
H H16 0.6955 0.9915 0.6138 0.025 Uiso calc U . R 1 . .
C C17 0.3026(3) 0.9857(3) 0.7113(2) 0.0148(5) Uani d . . . 1 . .
C C18 0.1938(3) 0.9854(3) 0.8140(2) 0.0191(6) Uani d . . . 1 . .
H H18 0.1776 0.8951 0.8559 0.023 Uiso calc U . R 1 . .
C C19 0.1087(3) 1.1153(3) 0.8560(2) 0.0207(6) Uani d . . . 1 . .
H H19 0.0341 1.1138 0.9258 0.025 Uiso calc U . R 1 . .
C C20 0.1331(3) 1.2472(3) 0.7958(2) 0.0196(6) Uani d . . . 1 . .
H H20 0.075 1.3363 0.8243 0.024 Uiso calc U . R 1 . .
C C21 0.2421(3) 1.2494(3) 0.6940(3) 0.0216(6) Uani d . . . 1 . .
H H21 0.2595 1.3398 0.6532 0.026 Uiso calc U . R 1 . .
C C22 0.3257(3) 1.1192(3) 0.6516(2) 0.0188(6) Uani d . . . 1 . .
H H22 0.3994 1.1212 0.5813 0.023 Uiso calc U . R 1 . .
C C1S 0.2323(3) 0.5099(3) 0.9337(3) 0.0252(7) Uani d . . . 1 . .
H H1S 0.2049 0.4167 0.9722 0.03 Uiso calc U . R 1 . .
Cl Cl1S 0.07522(10) 0.62569(8) 0.87084(8) 0.0334(2) Uani d . . . 1 . .
Cl Cl2S 0.26748(10) 0.59389(10) 1.04036(7) 0.0364(2) Uani d . . . 1 . .
Cl Cl3S 0.39652(10) 0.46836(9) 0.82586(7) 0.0336(2) Uani d . . . 1 . .
N N1 0.6229(3) 0.5614(2) 0.57941(19) 0.0141(5) Uani d . . . 1 . .
N N2 0.6523(3) 0.3252(2) 0.45330(19) 0.0146(5) Uani d . . . 1 . .
H H1A 0.531(6) 0.389(5) 0.454(4) 0.078(15) Uiso d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.370(4) ?
C1 C10 2_666 1.422(4) ?
C1 C2 . 1.441(4) ?
C2 C3 . 1.364(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.433(4) ?
C3 H3 . 0.95 ?
C4 N2 . 1.357(4) ?
C4 C5 . 1.407(4) ?
C5 N1 . 1.361(4) ?
C5 C6 . 1.431(4) ?
C6 C7 . 1.357(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.444(4) ?
C7 H7 . 0.95 ?
C8 N1 . 1.370(4) ?
C8 C9 . 1.417(4) ?
C9 C10 . 1.405(5) ?
C9 C11 . 1.505(4) ?
C10 C1 2_666 1.422(4) ?
C10 C17 . 1.508(4) ?
C11 C16 . 1.389(4) ?
C11 C12 . 1.404(4) ?
C12 C13 . 1.391(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.385(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.390(5) ?
C14 H14 . 0.95 ?
C15 C16 . 1.382(4) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 C18 . 1.391(4) ?
C17 C22 . 1.394(4) ?
C18 C19 . 1.388(4) ?
C18 H18 . 0.95 ?
C19 C20 . 1.386(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.386(4) ?
C20 H20 . 0.95 ?
C21 C22 . 1.389(4) ?
C21 H21 . 0.95 ?
C22 H22 . 0.95 ?
C1S Cl3S . 1.749(4) ?
C1S Cl2S . 1.759(4) ?
C1S Cl1S . 1.772(4) ?
C1S H1S . 1.0 ?
N2 H1A . 1.11(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C10 . 2_666 126.0(2) ?
N2 C1 C2 . . 107.1(2) ?
C10 C1 C2 2_666 . 126.9(3) ?
C3 C2 C1 . . 107.9(2) ?
C3 C2 H2 . . 126.0 ?
C1 C2 H2 . . 126.0 ?
C2 C3 C4 . . 107.0(3) ?
C2 C3 H3 . . 126.5 ?
C4 C3 H3 . . 126.5 ?
N2 C4 C5 . . 122.8(2) ?
N2 C4 C3 . . 108.5(3) ?
C5 C4 C3 . . 128.8(3) ?
N1 C5 C4 . . 122.6(3) ?
N1 C5 C6 . . 109.9(3) ?
C4 C5 C6 . . 127.6(2) ?
C7 C6 C5 . . 106.6(3) ?
C7 C6 H6 . . 126.7 ?
C5 C6 H6 . . 126.7 ?
C6 C7 C8 . . 107.6(3) ?
C6 C7 H7 . . 126.2 ?
C8 C7 H7 . . 126.2 ?
N1 C8 C9 . . 126.4(3) ?
N1 C8 C7 . . 108.3(2) ?
C9 C8 C7 . . 125.3(3) ?
C10 C9 C8 . . 129.7(3) ?
C10 C9 C11 . . 117.4(2) ?
C8 C9 C11 . . 112.9(3) ?
C9 C10 C1 . 2_666 129.6(3) ?
C9 C10 C17 . . 117.8(2) ?
C1 C10 C17 2_666 . 112.6(3) ?
C16 C11 C12 . . 118.6(3) ?
C16 C11 C9 . . 121.9(3) ?
C12 C11 C9 . . 119.5(3) ?
C13 C12 C11 . . 120.4(3) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.2(3) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 119.7(3) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C16 C15 C14 . . 120.2(3) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C11 . . 121.0(3) ?
C15 C16 H16 . . 119.5 ?
C11 C16 H16 . . 119.5 ?
C18 C17 C22 . . 118.8(2) ?
C18 C17 C10 . . 120.9(2) ?
C22 C17 C10 . . 120.3(3) ?
C19 C18 C17 . . 120.9(3) ?
C19 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C20 C19 C18 . . 119.8(3) ?
C20 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C19 C20 C21 . . 120.1(3) ?
C19 C20 H20 . . 120.0 ?
C21 C20 H20 . . 120.0 ?
C20 C21 C22 . . 119.9(3) ?
C20 C21 H21 . . 120.0 ?
C22 C21 H21 . . 120.0 ?
C21 C22 C17 . . 120.6(3) ?
C21 C22 H22 . . 119.7 ?
C17 C22 H22 . . 119.7 ?
Cl3S C1S Cl2S . . 110.7(2) ?
Cl3S C1S Cl1S . . 110.6(2) ?
Cl2S C1S Cl1S . . 109.9(2) ?
Cl3S C1S H1S . . 108.5 ?
Cl2S C1S H1S . . 108.5 ?
Cl1S C1S H1S . . 108.5 ?
C5 N1 C8 . . 107.6(3) ?
C4 N2 C1 . . 109.5(2) ?
C4 N2 H1A . . 134.(2) ?
C1 N2 H1A . . 117.(2) ?



####################################################################### 
# 
# 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_h911
_database_code_depnum_ccdc_archive 'CCDC 1868293'
_audit_update_record             
;
2018-09-18 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H46 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         726.93

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7406(11)
_cell_length_b                   15.369(2)
_cell_length_c                   16.406(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.303(4)
_cell_angle_gamma                90
_cell_volume                     2144.8(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    658
_cell_measurement_theta_min      2.5544
_cell_measurement_theta_max      30.3624
_cell_measurement_temperature    103.0(2)

_exptl_crystal_description       column
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.072
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772

_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.0(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            32049
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             4877
_reflns_number_gt                3778
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1848
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.104
_refine_ls_number_reflns         4877
_refine_ls_number_parameters     262
_refine_ls_number_restraints     168
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0907P)²+1.2790P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.467
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.044(4)

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.7 RC2'
_computing_cell_refinement       'APEX3 v2017.7-RC3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 853)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N001 0.39430(16) 0.40163(9) 0.44376(9) 0.0191(3) Uani d U . . 1 . .
N N002 0.35850(17) 0.51808(9) 0.57512(9) 0.0195(3) Uani d U . . 1 . .
C C003 0.2684(2) 0.39876(11) 0.47880(11) 0.0199(4) Uani d U . . 1 . .
C C004 0.36951(19) 0.34168(11) 0.38061(10) 0.0192(4) Uani d U . . 1 . .
C C005 0.3067(2) 0.56592(11) 0.63358(10) 0.0208(4) Uani d U . . 1 . .
C C006 0.5274(2) 0.67815(11) 0.67242(10) 0.0201(4) Uani d U . . 1 . .
C C007 0.5861(2) 0.75076(12) 0.73311(11) 0.0229(4) Uani d U . . 1 . .
C C008 0.6381(2) 0.73224(13) 0.81811(11) 0.0262(4) Uani d U . . 1 . .
H H008 0.632415 0.674253 0.837256 0.031 Uiso calc U . R 1 . .
C C009 0.2186(2) 0.30019(12) 0.37571(11) 0.0234(4) Uani d U . . 1 . .
H H009 0.171609 0.256704 0.336771 0.028 Uiso calc U . R 1 . .
C C00A 0.1571(2) 0.33500(12) 0.43699(12) 0.0242(4) Uani d U . . 1 . .
H H00A 0.059724 0.320248 0.449827 0.029 Uiso calc U . R 1 . .
C C00B 0.3833(2) 0.63932(11) 0.67723(10) 0.0210(4) Uani d U . . 1 . .
C C00C 0.2527(2) 0.45456(11) 0.54426(11) 0.0200(4) Uani d U . . 1 . .
C C00D 0.5934(2) 0.83594(12) 0.70583(12) 0.0264(4) Uani d U . . 1 . .
H H00D 0.557029 0.849015 0.648008 0.032 Uiso calc U . R 1 . .
C C00E 0.1274(2) 0.46027(12) 0.58640(11) 0.0247(4) Uani d U . . 1 . .
H H00E 0.038027 0.423289 0.578255 0.03 Uiso calc U . R 1 . .
C C00F 0.1597(2) 0.52872(12) 0.64060(11) 0.0248(4) Uani d U . . 1 . .
H H00F 0.095967 0.548326 0.676668 0.03 Uiso calc U . R 1 . .
C C00G 0.2897(2) 0.68269(13) 0.73218(12) 0.0285(4) Uani d U . . 1 . .
C C00H 0.6983(2) 0.79740(14) 0.87535(12) 0.0303(5) Uani d U . . 1 . .
C C00I 0.7056(2) 0.88172(14) 0.84621(13) 0.0323(5) Uani d U . . 1 . .
H H00I 0.747532 0.926433 0.884907 0.039 Uiso calc U . R 1 . .
C C00J 0.6531(2) 0.90257(13) 0.76187(14) 0.0313(5) Uani d U . . 1 . .
C C00K 0.2202(2) 0.76285(14) 0.70745(15) 0.0344(5) Uani d U . . 1 . .
H H00K 0.235368 0.789465 0.657646 0.041 Uiso calc U . R 1 . .
C C00L 0.2660(3) 0.64410(16) 0.80492(14) 0.0417(6) Uani d U . . 1 . .
H H00L 0.312727 0.589253 0.821915 0.05 Uiso calc U . R 1 . .
C C00M 0.7544(3) 0.77603(18) 0.96679(13) 0.0443(6) Uani d U . . 1 . .
H H00B 0.866932 0.78889 0.984956 0.066 Uiso calc U . R 1 . .
H H00C 0.736585 0.714139 0.975632 0.066 Uiso calc U . R 1 . .
H H00G 0.696247 0.811122 0.999385 0.066 Uiso calc U . R 1 . .
C C00N 0.6617(3) 0.99458(14) 0.73116(17) 0.0436(6) Uani d U . . 1 . .
H H00H 0.702095 1.032962 0.778967 0.065 Uiso calc U . R 1 . .
H H00J 0.556425 1.01389 0.702018 0.065 Uiso calc U . R 1 . .
H H00M 0.732072 0.996662 0.692546 0.065 Uiso calc U . R 1 . .
C C00O 0.1281(3) 0.80473(17) 0.75504(19) 0.0518(7) Uani d U . . 1 . .
C C00P 0.1749(4) 0.6845(2) 0.85333(18) 0.0598(8) Uani d U . . 1 . .
C C00Q 0.1077(3) 0.7644(2) 0.8272(2) 0.0642(9) Uani d U . . 1 . .
H H00Q 0.04566 0.79243 0.859971 0.077 Uiso calc U . R 1 . .
C C00R 0.0530(3) 0.89066(18) 0.7264(2) 0.0748(11) Uani d U . . 1 . .
H H00N -0.034845 0.881589 0.6779 0.112 Uiso calc U . R 1 . .
H H00O 0.130791 0.929154 0.710643 0.112 Uiso calc U . R 1 . .
H H00P 0.013891 0.917339 0.771937 0.112 Uiso calc U . R 1 . .
C C00S 0.1482(5) 0.6424(3) 0.9310(2) 0.0996(16) Uani d U . . 1 . .
H H00R 0.197172 0.677646 0.979853 0.149 Uiso calc U . R 1 . .
H H00S 0.195026 0.584134 0.936694 0.149 Uiso calc U . R 1 . .
H H00T 0.035057 0.637813 0.927453 0.149 Uiso calc U . R 1 . .
H H1N 0.450(4) 0.5371(18) 0.5537(18) 0.060(8) Uiso d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N001 C003 . 1.354(2) ?
N001 C004 . 1.366(2) ?
N002 C00C . 1.360(2) ?
N002 C005 . 1.366(2) ?
N002 H1N . 0.99(3) ?
C003 C00C . 1.406(2) ?
C003 C00A . 1.439(2) ?
C004 C006 3_666 1.422(2) ?
C004 C009 . 1.451(2) ?
C005 C00B . 1.419(2) ?
C005 C00F . 1.435(2) ?
C006 C00B . 1.412(2) ?
C006 C007 . 1.505(2) ?
C007 C00D . 1.390(3) ?
C007 C008 . 1.393(3) ?
C008 C00H . 1.391(3) ?
C008 H008 . 0.95 ?
C009 C00A . 1.354(3) ?
C009 H009 . 0.95 ?
C00A H00A . 0.95 ?
C00B C00G . 1.505(2) ?
C00C C00E . 1.426(2) ?
C00D C00J . 1.395(3) ?
C00D H00D . 0.95 ?
C00E C00F . 1.364(3) ?
C00E H00E . 0.95 ?
C00F H00F . 0.95 ?
C00G C00L . 1.390(3) ?
C00G C00K . 1.392(3) ?
C00H C00I . 1.388(3) ?
C00H C00M . 1.503(3) ?
C00I C00J . 1.391(3) ?
C00I H00I . 0.95 ?
C00J C00N . 1.509(3) ?
C00K C00O . 1.400(3) ?
C00K H00K . 0.95 ?
C00L C00P . 1.394(3) ?
C00L H00L . 0.95 ?
C00M H00B . 0.98 ?
C00M H00C . 0.98 ?
C00M H00G . 0.98 ?
C00N H00H . 0.98 ?
C00N H00J . 0.98 ?
C00N H00M . 0.98 ?
C00O C00Q . 1.384(4) ?
C00O C00R . 1.501(4) ?
C00P C00Q . 1.385(5) ?
C00P C00S . 1.495(4) ?
C00Q H00Q . 0.95 ?
C00R H00N . 0.98 ?
C00R H00O . 0.98 ?
C00R H00P . 0.98 ?
C00S H00R . 0.98 ?
C00S H00S . 0.98 ?
C00S H00T . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C003 N001 C004 . . 107.30(14) ?
C00C N002 C005 . . 109.94(15) ?
C00C N002 H1N . . 128.0(16) ?
C005 N002 H1N . . 121.1(16) ?
N001 C003 C00C . . 122.43(15) ?
N001 C003 C00A . . 110.26(15) ?
C00C C003 C00A . . 127.26(16) ?
N001 C004 C006 . 3_666 126.61(15) ?
N001 C004 C009 . . 108.79(15) ?
C006 C004 C009 3_666 . 124.60(16) ?
N002 C005 C00B . . 126.03(16) ?
N002 C005 C00F . . 106.84(15) ?
C00B C005 C00F . . 127.13(16) ?
C00B C006 C004 . 3_666 129.96(16) ?
C00B C006 C007 . . 116.68(15) ?
C004 C006 C007 3_666 . 113.35(15) ?
C00D C007 C008 . . 119.11(17) ?
C00D C007 C006 . . 121.28(16) ?
C008 C007 C006 . . 119.59(16) ?
C00H C008 C007 . . 120.95(19) ?
C00H C008 H008 . . 119.5 ?
C007 C008 H008 . . 119.5 ?
C00A C009 C004 . . 107.23(15) ?
C00A C009 H009 . . 126.4 ?
C004 C009 H009 . . 126.4 ?
C009 C00A C003 . . 106.41(16) ?
C009 C00A H00A . . 126.8 ?
C003 C00A H00A . . 126.8 ?
C006 C00B C005 . . 129.14(16) ?
C006 C00B C00G . . 117.45(15) ?
C005 C00B C00G . . 113.32(15) ?
N002 C00C C003 . . 123.01(15) ?
N002 C00C C00E . . 107.93(15) ?
C003 C00C C00E . . 128.97(16) ?
C007 C00D C00J . . 121.14(19) ?
C007 C00D H00D . . 119.4 ?
C00J C00D H00D . . 119.4 ?
C00F C00E C00C . . 107.25(16) ?
C00F C00E H00E . . 126.4 ?
C00C C00E H00E . . 126.4 ?
C00E C00F C005 . . 108.04(16) ?
C00E C00F H00F . . 126.0 ?
C005 C00F H00F . . 126.0 ?
C00L C00G C00K . . 119.1(2) ?
C00L C00G C00B . . 122.3(2) ?
C00K C00G C00B . . 118.57(18) ?
C00I C00H C008 . . 118.68(19) ?
C00I C00H C00M . . 121.17(19) ?
C008 C00H C00M . . 120.2(2) ?
C00H C00I C00J . . 121.79(18) ?
C00H C00I H00I . . 119.1 ?
C00J C00I H00I . . 119.1 ?
C00I C00J C00D . . 118.31(19) ?
C00I C00J C00N . . 121.16(19) ?
C00D C00J C00N . . 120.5(2) ?
C00G C00K C00O . . 120.8(2) ?
C00G C00K H00K . . 119.6 ?
C00O C00K H00K . . 119.6 ?
C00G C00L C00P . . 121.1(3) ?
C00G C00L H00L . . 119.5 ?
C00P C00L H00L . . 119.5 ?
C00H C00M H00B . . 109.5 ?
C00H C00M H00C . . 109.5 ?
H00B C00M H00C . . 109.5 ?
C00H C00M H00G . . 109.5 ?
H00B C00M H00G . . 109.5 ?
H00C C00M H00G . . 109.5 ?
C00J C00N H00H . . 109.5 ?
C00J C00N H00J . . 109.5 ?
H00H C00N H00J . . 109.5 ?
C00J C00N H00M . . 109.5 ?
H00H C00N H00M . . 109.5 ?
H00J C00N H00M . . 109.5 ?
C00Q C00O C00K . . 118.3(3) ?
C00Q C00O C00R . . 121.9(2) ?
C00K C00O C00R . . 119.7(3) ?
C00Q C00P C00L . . 118.4(3) ?
C00Q C00P C00S . . 120.6(3) ?
C00L C00P C00S . . 121.0(3) ?
C00O C00Q C00P . . 122.2(2) ?
C00O C00Q H00Q . . 118.9 ?
C00P C00Q H00Q . . 118.9 ?
C00O C00R H00N . . 109.5 ?
C00O C00R H00O . . 109.5 ?
H00N C00R H00O . . 109.5 ?
C00O C00R H00P . . 109.5 ?
H00N C00R H00P . . 109.5 ?
H00O C00R H00P . . 109.5 ?
C00P C00S H00R . . 109.5 ?
C00P C00S H00S . . 109.5 ?
H00R C00S H00S . . 109.5 ?
C00P C00S H00T . . 109.5 ?
H00R C00S H00T . . 109.5 ?
H00S C00S H00T . . 109.5 ?



####################################################################### 
# 
# 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_xu1_bruker2
_database_code_depnum_ccdc_archive 'CCDC 1868294'
_audit_update_record             
;
2018-09-18 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H26 Cl2 F8 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         857.61

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4081(6)
_cell_length_b                   13.0237(9)
_cell_length_c                   17.9996(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.022(2)
_cell_angle_gamma                90
_cell_volume                     1920.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      25.2
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872

_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            86147
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3444
_reflns_number_gt                2613
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1716
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_number_reflns         3444
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+3.5703P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.507
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.32988(19) 0.38461(11) 0.02038(8) 0.0669(6) Uani d . P . 0.793(5) . .
F F1 0.0236(2) 0.92340(15) 0.73528(12) 0.0467(5) Uani d . . . 1.0 . .
F F2 0.2009(3) 0.64340(19) 0.89663(11) 0.0539(6) Uani d . . . 1.0 . .
F F4 0.7697(3) 0.8554(2) 0.89972(12) 0.0643(7) Uani d . . . 1.0 . .
F F3 0.6269(3) 1.08343(16) 0.69400(18) 0.0720(8) Uani d . . . 1.0 . .
N N2 0.3958(3) 0.37908(18) 0.45271(13) 0.0257(5) Uani d . . . 1.0 . .
N N1 0.3499(3) 0.52465(18) 0.56543(13) 0.0261(5) Uani d . . . 1.0 . .
H H1 0.4392 0.5369 0.5492 0.031 Uiso calc U . R 1.0 . .
C C4 0.2646(3) 0.3761(2) 0.48500(15) 0.0254(6) Uani d . . . 1.0 . .
C C5 0.2433(3) 0.4470(2) 0.54035(15) 0.0256(6) Uani d . . . 1.0 . .
C C1 0.3770(3) 0.3017(2) 0.39996(16) 0.0262(6) Uani d . . . 1.0 . .
C C8 0.2981(3) 0.5809(2) 0.61944(16) 0.0262(6) Uani d . . . 1.0 . .
C C6 0.1142(4) 0.4532(2) 0.58037(16) 0.0293(7) Uani d . . . 1.0 . .
H H6 0.0225 0.4088 0.5742 0.035 Uiso calc U . R 1.0 . .
C C7 0.1477(4) 0.5347(2) 0.62883(16) 0.0292(6) Uani d . . . 1.0 . .
H H7 0.0834 0.5572 0.6628 0.035 Uiso calc U . R 1.0 . .
C C9 0.3758(4) 0.6684(2) 0.65787(16) 0.0279(6) Uani d . . . 1.0 . .
C C3 0.1574(4) 0.2942(2) 0.45259(16) 0.0291(7) Uani d . . . 1.0 . .
H H3 0.0579 0.2757 0.4656 0.035 Uiso calc U . R 1.0 . .
C C2 0.2257(4) 0.2485(2) 0.39985(17) 0.0299(7) Uani d . . . 1.0 . .
H H2 0.1823 0.1919 0.3685 0.036 Uiso calc U . R 1.0 . .
C C10 0.5173(3) 0.7196(2) 0.64961(16) 0.0267(6) Uani d . . . 1.0 . .
C C11 0.2869(4) 0.7108(2) 0.71491(16) 0.0295(7) Uani d . . . 1.0 . .
C C12 0.1988(4) 0.8019(2) 0.69958(18) 0.0323(7) Uani d . . . 1.0 . .
H H12 0.1983 0.8399 0.6545 0.039 Uiso calc U . R 1.0 . .
C C17 0.5746(4) 0.8089(2) 0.70213(18) 0.0321(7) Uani d . . . 1.0 . .
C C13 0.1124(4) 0.8353(2) 0.75161(19) 0.0359(7) Uani d . . . 1.0 . .
C C16 0.2876(4) 0.6578(3) 0.78206(17) 0.0340(7) Uani d . . . 1.0 . .
H H16 0.3481 0.596 0.7936 0.041 Uiso calc U . R 1.0 . .
C C22 0.5667(4) 0.9080(3) 0.6733(2) 0.0390(8) Uani d . . . 1.0 . .
H H22 0.5194 0.9214 0.6211 0.047 Uiso calc U . R 1.0 . .
C C15 0.1996(4) 0.6962(3) 0.83148(17) 0.0384(8) Uani d . . . 1.0 . .
C C14 0.1088(4) 0.7851(3) 0.81842(18) 0.0379(8) Uani d . . . 1.0 . .
H H14 0.0479 0.8099 0.8532 0.045 Uiso calc U . R 1.0 . .
C C18 0.6428(4) 0.7907(3) 0.77895(18) 0.0374(8) Uani d . . . 1.0 . .
H H18 0.6487 0.7231 0.7992 0.045 Uiso calc U . R 1.0 . .
C C19 0.7016(4) 0.8734(3) 0.8248(2) 0.0472(9) Uani d . . . 1.0 . .
C C21 0.6298(4) 0.9866(3) 0.7230(3) 0.0492(10) Uani d . . . 1.0 . .
C C20 0.6981(4) 0.9726(3) 0.7988(2) 0.0521(10) Uani d . . . 1.0 . .
H H20 0.7406 1.0281 0.8315 0.063 Uiso calc U . R 1.0 . .
C C1S 0.4533(7) 0.5026(3) 0.0315(3) 0.0520(13) Uani d . P . 0.793(5) . .
H H1S1 0.3826 0.5643 0.0256 0.062 Uiso calc U P R 0.793(5) . .
H H1S2 0.5293 0.5048 0.0823 0.062 Uiso calc U P R 0.793(5) . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1S . 1.840(5) ?
F1 C13 . 1.364(4) ?
F2 C15 . 1.358(4) ?
F4 C19 . 1.361(4) ?
F3 C21 . 1.363(5) ?
N2 C4 . 1.358(4) ?
N2 C1 . 1.369(4) ?
N1 C5 . 1.360(4) ?
N1 C8 . 1.364(4) ?
N1 H1 . 0.88 ?
C4 C5 . 1.399(4) ?
C4 C3 . 1.432(4) ?
C5 C6 . 1.434(4) ?
C1 C10 3_666 1.421(4) ?
C1 C2 . 1.449(4) ?
C8 C9 . 1.414(4) ?
C8 C7 . 1.444(4) ?
C6 C7 . 1.363(4) ?
C6 H6 . 0.95 ?
C7 H7 . 0.95 ?
C9 C10 . 1.401(4) ?
C9 C11 . 1.505(4) ?
C3 C2 . 1.353(4) ?
C3 H3 . 0.95 ?
C2 H2 . 0.95 ?
C10 C1 3_666 1.421(4) ?
C10 C17 . 1.508(4) ?
C11 C16 . 1.391(4) ?
C11 C12 . 1.392(4) ?
C12 C13 . 1.379(4) ?
C12 H12 . 0.95 ?
C17 C22 . 1.387(5) ?
C17 C18 . 1.393(5) ?
C13 C14 . 1.376(5) ?
C16 C15 . 1.374(4) ?
C16 H16 . 0.95 ?
C22 C21 . 1.384(5) ?
C22 H22 . 0.95 ?
C15 C14 . 1.377(5) ?
C14 H14 . 0.95 ?
C18 C19 . 1.379(5) ?
C18 H18 . 0.95 ?
C19 C20 . 1.372(6) ?
C21 C20 . 1.369(6) ?
C20 H20 . 0.95 ?
C1S C1S 3_665 1.521(9) ?
C1S H1S1 . 0.99 ?
C1S H1S2 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N2 C1 . . 107.3(2) ?
C5 N1 C8 . . 110.1(2) ?
C5 N1 H1 . . 124.9 ?
C8 N1 H1 . . 124.9 ?
N2 C4 C5 . . 122.2(3) ?
N2 C4 C3 . . 110.1(2) ?
C5 C4 C3 . . 127.7(3) ?
N1 C5 C4 . . 123.2(3) ?
N1 C5 C6 . . 107.9(2) ?
C4 C5 C6 . . 128.9(3) ?
N2 C1 C10 . 3_666 126.1(3) ?
N2 C1 C2 . . 108.5(2) ?
C10 C1 C2 3_666 . 125.4(3) ?
N1 C8 C9 . . 126.5(3) ?
N1 C8 C7 . . 106.8(2) ?
C9 C8 C7 . . 126.7(3) ?
C7 C6 C5 . . 107.2(3) ?
C7 C6 H6 . . 126.4 ?
C5 C6 H6 . . 126.4 ?
C6 C7 C8 . . 108.0(2) ?
C6 C7 H7 . . 126.0 ?
C8 C7 H7 . . 126.0 ?
C10 C9 C8 . . 129.9(3) ?
C10 C9 C11 . . 117.5(3) ?
C8 C9 C11 . . 112.6(2) ?
C2 C3 C4 . . 106.6(3) ?
C2 C3 H3 . . 126.7 ?
C4 C3 H3 . . 126.7 ?
C3 C2 C1 . . 107.5(3) ?
C3 C2 H2 . . 126.3 ?
C1 C2 H2 . . 126.3 ?
C9 C10 C1 . 3_666 129.8(3) ?
C9 C10 C17 . . 117.4(2) ?
C1 C10 C17 3_666 . 112.8(3) ?
C16 C11 C12 . . 119.5(3) ?
C16 C11 C9 . . 120.3(3) ?
C12 C11 C9 . . 120.1(3) ?
C13 C12 C11 . . 118.2(3) ?
C13 C12 H12 . . 120.9 ?
C11 C12 H12 . . 120.9 ?
C22 C17 C18 . . 120.3(3) ?
C22 C17 C10 . . 120.1(3) ?
C18 C17 C10 . . 119.6(3) ?
F1 C13 C14 . . 118.0(3) ?
F1 C13 C12 . . 117.8(3) ?
C14 C13 C12 . . 124.2(3) ?
C15 C16 C11 . . 119.0(3) ?
C15 C16 H16 . . 120.5 ?
C11 C16 H16 . . 120.5 ?
C21 C22 C17 . . 117.8(3) ?
C21 C22 H22 . . 121.1 ?
C17 C22 H22 . . 121.1 ?
F2 C15 C16 . . 118.3(3) ?
F2 C15 C14 . . 118.0(3) ?
C16 C15 C14 . . 123.7(3) ?
C13 C14 C15 . . 115.4(3) ?
C13 C14 H14 . . 122.3 ?
C15 C14 H14 . . 122.3 ?
C19 C18 C17 . . 118.3(3) ?
C19 C18 H18 . . 120.9 ?
C17 C18 H18 . . 120.9 ?
F4 C19 C20 . . 118.1(3) ?
F4 C19 C18 . . 118.2(4) ?
C20 C19 C18 . . 123.7(4) ?
F3 C21 C20 . . 118.2(3) ?
F3 C21 C22 . . 117.8(4) ?
C20 C21 C22 . . 124.0(4) ?
C21 C20 C19 . . 116.0(3) ?
C21 C20 H20 . . 122.0 ?
C19 C20 H20 . . 122.0 ?
C1S C1S Cl1 3_665 . 104.7(5) ?
C1S C1S H1S1 3_665 . 110.8 ?
Cl1 C1S H1S1 . . 110.8 ?
C1S C1S H1S2 3_665 . 110.8 ?
Cl1 C1S H1S2 . . 110.8 ?
H1S1 C1S H1S2 . . 108.9 ?



