# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1051367'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Br F2 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         398.24
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   11.1103(4)
_cell_length_b                   19.8612(7)
_cell_length_c                   8.6893(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.1045(15)
_cell_angle_gamma                90
_cell_volume                     1675.31(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3705
_cell_measurement_theta_min      2.3352
_cell_measurement_theta_max      26.4533
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    2.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.64

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            11979
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_full        31.02
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11

_refine_special_details          'Refined as a 2-component inversion twin.'

_reflns_number_total             4527
_reflns_number_gt                3928
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_gt          0.0635
_refine_ls_wR_factor_ref         0.0666
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_number_reflns         4527
_refine_ls_number_parameters     226
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1446 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(6)

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

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
Br Br1 -0.49980(4) 0.55433(2) 0.25015(4) 0.02357(9) Uani d . . . 1 . .
C C1 0.2263(4) 0.57442(16) 0.7204(4) 0.0174(6) Uani d . . . 1 . .
H H1 0.3195 0.5691 0.8092 0.021 Uiso calc U . R 1 . .
C C2 0.1259(4) 0.55299(15) 0.7531(4) 0.0181(7) Uani d . . . 1 . .
H H2 0.1554 0.5318 0.8638 0.022 Uiso calc U . R 1 . .
C C3 -0.0234(4) 0.55849(15) 0.6385(4) 0.0157(6) Uani d . . . 1 . .
C C4 -0.1100(4) 0.51282(16) 0.6629(4) 0.0178(7) Uani d . . . 1 . .
H H4 -0.0704 0.482 0.7584 0.021 Uiso calc U . R 1 . .
C C5 -0.2499(4) 0.51175(16) 0.5522(4) 0.0191(7) Uani d . . . 1 . .
H H5 -0.3062 0.4801 0.57 0.023 Uiso calc U . R 1 . .
C C6 -0.3084(4) 0.55763(15) 0.4136(4) 0.0178(6) Uani d . . . 1 . .
C C7 -0.2276(4) 0.60602(16) 0.3928(4) 0.0188(7) Uani d . . . 1 . .
H H7 -0.269 0.639 0.3027 0.023 Uiso calc U . R 1 . .
C C8 -0.0868(4) 0.60632(15) 0.5032(4) 0.0181(7) Uani d . . . 1 . .
H H8 -0.0319 0.6394 0.4875 0.022 Uiso calc U . R 1 . .
C C9 0.2948(3) 0.63485(16) 0.5456(4) 0.0144(6) Uani d . . . 1 . .
C C10 0.2612(3) 0.65899(15) 0.3665(4) 0.0142(6) Uani d . . . 1 . .
C C11 0.3471(4) 0.70443(15) 0.3427(4) 0.0172(6) Uani d . . . 1 . .
H H11 0.4295 0.7195 0.4419 0.021 Uiso calc U . R 1 . .
C C12 0.3133(4) 0.72795(16) 0.1750(4) 0.0176(7) Uani d . . . 1 . .
H H12 0.3711 0.7589 0.1584 0.021 Uiso calc U . R 1 . .
C C13 0.1944(4) 0.70494(16) 0.0357(4) 0.0186(7) Uani d . . . 1 . .
C C14 0.1068(3) 0.65987(16) 0.0514(4) 0.0191(7) Uani d . . . 1 . .
H H14 0.0255 0.6447 -0.0492 0.023 Uiso calc U . R 1 . .
C C15 0.1409(4) 0.63726(16) 0.2189(4) 0.0184(6) Uani d . . . 1 . .
H H15 0.0816 0.6065 0.2333 0.022 Uiso calc U . R 1 . .
C C16 0.4352(3) 0.64876(16) 0.6933(4) 0.0162(6) Uani d . . . 1 . .
C C17 0.4545(4) 0.68776(15) 0.8370(4) 0.0175(6) Uani d . . . 1 . .
H H17 0.3766 0.705 0.8419 0.021 Uiso calc U . R 1 . .
C C18 0.5855(4) 0.70162(16) 0.9727(4) 0.0204(7) Uani d . . . 1 . .
H H18 0.5985 0.7292 1.069 0.024 Uiso calc U . R 1 . .
C C19 0.6967(4) 0.67441(18) 0.9650(4) 0.0201(7) Uani d . . . 1 . .
C C20 0.6823(4) 0.63569(16) 0.8250(5) 0.0202(7) Uani d . . . 1 . .
H H20 0.7606 0.6181 0.822 0.024 Uiso calc U . R 1 . .
C C21 0.5511(3) 0.62321(15) 0.6896(4) 0.0171(6) Uani d . . . 1 . .
H H21 0.5392 0.5968 0.5921 0.021 Uiso calc U . R 1 . .
F F1 0.1591(2) 0.72796(10) -0.1296(2) 0.0248(5) Uani d . . . 1 . .
F F2 0.8251(2) 0.68652(11) 1.0984(3) 0.0271(5) Uani d . . . 1 . .
N N1 0.1986(3) 0.60427(13) 0.5605(3) 0.0175(6) Uani 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
Br1 C6 . 1.899(4) ?
C1 C2 . 1.347(5) ?
C1 N1 . 1.400(4) ?
C2 C3 . 1.466(5) ?
C3 C8 . 1.405(4) ?
C3 C4 . 1.411(4) ?
C4 C5 . 1.374(5) ?
C5 C6 . 1.394(5) ?
C6 C7 . 1.386(5) ?
C7 C8 . 1.381(5) ?
C9 N1 . 1.290(4) ?
C9 C16 . 1.486(4) ?
C9 C10 . 1.492(4) ?
C10 C15 . 1.396(4) ?
C10 C11 . 1.400(4) ?
C11 C12 . 1.397(4) ?
C12 C13 . 1.365(5) ?
C13 F1 . 1.370(3) ?
C13 C14 . 1.377(4) ?
C14 C15 . 1.388(4) ?
C16 C17 . 1.395(4) ?
C16 C21 . 1.399(4) ?
C17 C18 . 1.384(5) ?
C18 C19 . 1.380(5) ?
C19 F2 . 1.352(4) ?
C19 C20 . 1.381(5) ?
C20 C21 . 1.379(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
C2 C1 N1 . . 122.6(3) ?
C1 C2 C3 . . 127.8(3) ?
C8 C3 C4 . . 117.4(3) ?
C8 C3 C2 . . 124.0(3) ?
C4 C3 C2 . . 118.6(3) ?
C5 C4 C3 . . 121.8(3) ?
C4 C5 C6 . . 119.2(3) ?
C7 C6 C5 . . 120.5(3) ?
C7 C6 Br1 . . 119.2(3) ?
C5 C6 Br1 . . 120.3(3) ?
C8 C7 C6 . . 119.9(3) ?
C7 C8 C3 . . 121.0(3) ?
N1 C9 C16 . . 125.0(3) ?
N1 C9 C10 . . 117.2(3) ?
C16 C9 C10 . . 117.8(3) ?
C15 C10 C11 . . 118.7(3) ?
C15 C10 C9 . . 120.1(3) ?
C11 C10 C9 . . 121.2(3) ?
C12 C11 C10 . . 120.9(3) ?
C13 C12 C11 . . 117.8(3) ?
C12 C13 F1 . . 118.5(3) ?
C12 C13 C14 . . 123.7(3) ?
F1 C13 C14 . . 117.7(3) ?
C13 C14 C15 . . 117.9(3) ?
C14 C15 C10 . . 121.0(3) ?
C17 C16 C21 . . 118.7(3) ?
C17 C16 C9 . . 121.1(3) ?
C21 C16 C9 . . 120.3(3) ?
C18 C17 C16 . . 120.9(3) ?
C19 C18 C17 . . 118.4(3) ?
F2 C19 C18 . . 119.0(3) ?
F2 C19 C20 . . 118.5(3) ?
C18 C19 C20 . . 122.5(3) ?
C21 C20 C19 . . 118.3(3) ?
C20 C21 C16 . . 121.2(3) ?
C9 N1 C1 . . 120.4(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 1051368'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 F2 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         333.36

_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                   8.7580(7)
_cell_length_b                   9.0189(7)
_cell_length_c                   12.1251(9)
_cell_angle_alpha                77.130(4)
_cell_angle_beta                 80.995(4)
_cell_angle_gamma                74.079(5)
_cell_volume                     893.19(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1918
_cell_measurement_theta_min      2.4309
_cell_measurement_theta_max      22.7814
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            14211
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3508
_reflns_number_gt                1837
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1626
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         3508
_refine_ls_number_parameters     227
_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)+(0.0744P)²] 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         0.175
_refine_diff_density_min         -0.214
_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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

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 0.3744(3) 0.7151(3) 0.79895(19) 0.0486(6) Uani d . . . 1 . .
C C2 0.2345(3) 0.8528(2) 0.80893(18) 0.0477(6) Uani d . . . 1 . .
C C3 0.0893(3) 0.8573(3) 0.77508(19) 0.0525(6) Uani d . . . 1 . .
H H3 0.0789 0.7736 0.7463 0.063 Uiso calc U . R 1 . .
C C4 -0.0403(3) 0.9836(3) 0.7833(2) 0.0583(7) Uani d . . . 1 . .
H H4 -0.1374 0.9867 0.7598 0.07 Uiso calc U . R 1 . .
C C5 -0.0218(3) 1.1032(3) 0.8267(2) 0.0599(7) Uani d . . . 1 . .
C C6 0.1174(3) 1.1033(3) 0.8618(2) 0.0714(8) Uani d . . . 1 . .
H H6 0.1257 1.1869 0.8918 0.086 Uiso calc U . R 1 . .
C C7 0.2461(3) 0.9779(3) 0.8523(2) 0.0640(7) Uani d . . . 1 . .
H H7 0.3427 0.9771 0.8755 0.077 Uiso calc U . R 1 . .
C C8 0.3632(3) 0.5603(2) 0.86806(18) 0.0458(6) Uani d . . . 1 . .
C C9 0.4780(3) 0.4248(3) 0.8497(2) 0.0592(7) Uani d . . . 1 . .
H H9 0.5604 0.4321 0.7918 0.071 Uiso calc U . R 1 . .
C C10 0.4727(3) 0.2794(3) 0.9153(2) 0.0631(7) Uani d . . . 1 . .
H H10 0.5499 0.1895 0.9018 0.076 Uiso calc U . R 1 . .
C C11 0.3527(3) 0.2714(3) 0.9995(2) 0.0573(7) Uani d . . . 1 . .
C C12 0.2367(3) 0.3995(3) 1.0220(2) 0.0615(7) Uani d . . . 1 . .
H H12 0.1557 0.3899 1.0806 0.074 Uiso calc U . R 1 . .
C C13 0.2422(3) 0.5448(3) 0.9555(2) 0.0561(6) Uani d . . . 1 . .
H H13 0.1635 0.6334 0.9696 0.067 Uiso calc U . R 1 . .
C C14 0.5226(3) 0.8612(3) 0.6625(2) 0.0642(7) Uani d . . . 1 . .
H H14 0.4338 0.9463 0.656 0.077 Uiso calc U . R 1 . .
C C15 0.6599(3) 0.8793(3) 0.6022(2) 0.0655(7) Uani d . . . 1 . .
H H15 0.6536 0.9774 0.5556 0.079 Uiso calc U . R 1 . .
C C16 0.8176(3) 0.7716(3) 0.59700(19) 0.0578(6) Uani d . . . 1 . .
C C17 0.8620(3) 0.6252(3) 0.6665(2) 0.0630(7) Uani d . . . 1 . .
H H17 0.7868 0.5897 0.7215 0.076 Uiso calc U . R 1 . .
C C18 1.0147(3) 0.5314(3) 0.6557(2) 0.0688(7) Uani d . . . 1 . .
H H18 1.0404 0.4344 0.7041 0.083 Uiso calc U . R 1 . .
C C19 1.1307(3) 0.5778(4) 0.5747(3) 0.0756(8) Uani d . . . 1 . .
C C20 1.2981(4) 0.4744(5) 0.5654(3) 0.1138(13) Uani d . . . 1 . .
H H20A 1.3286 0.4586 0.4885 0.171 Uiso calc U . R 1 . .
H H20B 1.3018 0.3749 0.6154 0.171 Uiso calc U . R 1 . .
H H20C 1.3703 0.524 0.5865 0.171 Uiso calc U . R 1 . .
C C21 1.0862(4) 0.7223(4) 0.5046(3) 0.0877(10) Uani d . . . 1 . .
H H21 1.1612 0.7565 0.4487 0.105 Uiso calc U . R 1 . .
C C22 0.9346(4) 0.8171(4) 0.5151(2) 0.0774(8) Uani d . . . 1 . .
H H22 0.9095 0.9138 0.4663 0.093 Uiso calc U . R 1 . .
F F1 -0.14853(18) 1.22797(17) 0.83475(14) 0.0925(6) Uani d . . . 1 . .
F F2 0.34860(18) 0.12831(16) 1.06535(13) 0.0826(5) Uani d . . . 1 . .
N N1 0.5054(2) 0.7223(2) 0.73424(16) 0.0548(5) Uani 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 N1 . 1.293(3) ?
C1 C8 . 1.480(3) ?
C1 C2 . 1.498(3) ?
C2 C7 . 1.379(3) ?
C2 C3 . 1.384(3) ?
C3 C4 . 1.379(3) ?
C4 C5 . 1.358(3) ?
C5 C6 . 1.353(3) ?
C5 F1 . 1.356(3) ?
C6 C7 . 1.372(3) ?
C8 C13 . 1.389(3) ?
C8 C9 . 1.390(3) ?
C9 C10 . 1.382(3) ?
C10 C11 . 1.351(3) ?
C11 C12 . 1.361(3) ?
C11 F2 . 1.364(3) ?
C12 C13 . 1.386(3) ?
C14 C15 . 1.337(3) ?
C14 N1 . 1.388(3) ?
C15 C16 . 1.456(3) ?
C16 C17 . 1.389(3) ?
C16 C22 . 1.391(4) ?
C17 C18 . 1.376(3) ?
C18 C19 . 1.382(4) ?
C19 C21 . 1.380(4) ?
C19 C20 . 1.508(4) ?
C21 C22 . 1.372(4) ?

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
N1 C1 C8 . . 117.5(2) ?
N1 C1 C2 . . 124.4(2) ?
C8 C1 C2 . . 118.1(2) ?
C7 C2 C3 . . 118.1(2) ?
C7 C2 C1 . . 121.3(2) ?
C3 C2 C1 . . 120.6(2) ?
C4 C3 C2 . . 121.2(2) ?
C5 C4 C3 . . 118.0(2) ?
C6 C5 F1 . . 118.8(2) ?
C6 C5 C4 . . 122.9(2) ?
F1 C5 C4 . . 118.3(2) ?
C5 C6 C7 . . 118.7(2) ?
C6 C7 C2 . . 121.1(2) ?
C13 C8 C9 . . 117.5(2) ?
C13 C8 C1 . . 121.9(2) ?
C9 C8 C1 . . 120.5(2) ?
C10 C9 C8 . . 121.7(2) ?
C11 C10 C9 . . 118.3(2) ?
C10 C11 C12 . . 123.0(2) ?
C10 C11 F2 . . 118.4(2) ?
C12 C11 F2 . . 118.6(2) ?
C11 C12 C13 . . 118.4(2) ?
C12 C13 C8 . . 121.1(2) ?
C15 C14 N1 . . 123.6(2) ?
C14 C15 C16 . . 131.0(2) ?
C17 C16 C22 . . 116.5(3) ?
C17 C16 C15 . . 125.6(2) ?
C22 C16 C15 . . 117.9(3) ?
C18 C17 C16 . . 121.6(3) ?
C17 C18 C19 . . 121.6(3) ?
C21 C19 C18 . . 116.9(3) ?
C21 C19 C20 . . 122.3(3) ?
C18 C19 C20 . . 120.8(3) ?
C22 C21 C19 . . 122.0(3) ?
C21 C22 C16 . . 121.4(3) ?
C1 N1 C14 . . 121.1(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_I
_database_code_depnum_ccdc_archive 'CCDC 1051369'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Br3 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         558.11

_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                   9.8400(9)
_cell_length_b                   13.6565(13)
_cell_length_c                   15.8730(16)
_cell_angle_alpha                102.909(6)
_cell_angle_beta                 93.588(6)
_cell_angle_gamma                95.664(6)
_cell_volume                     2061.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3574
_cell_measurement_theta_min      2.7344
_cell_measurement_theta_max      21.4639
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088

_exptl_absorpt_coefficient_mu    5.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.65

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            40100
_diffrn_reflns_av_R_equivalents  0.1300
_diffrn_reflns_av_unetI/netI     0.1239
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             8099
_reflns_number_gt                4663
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1328
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1927
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         8099
_refine_ls_number_parameters     505
_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)+(0.0934P)²+0.8687P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.803
_refine_diff_density_min         -1.027
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

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
Br Br1 0.26648(12) 1.53152(8) 0.58105(7) 0.0466(3) Uani d . . . 1 . .
Br Br2 0.43183(10) 0.88153(8) 0.78072(6) 0.0378(3) Uani d . . . 1 . .
Br Br3 -0.32802(9) 0.52350(7) 0.03759(6) 0.0315(3) Uani d . . . 1 . .
Br Br4 0.51403(12) -0.40250(8) 0.78746(7) 0.0439(3) Uani d . . . 1 . .
Br Br5 0.41118(10) 0.25499(8) 0.59638(6) 0.0332(3) Uani d . . . 1 . .
Br Br6 1.20864(9) 0.58809(7) 1.33267(6) 0.0293(3) Uani d . . . 1 . .
C C1 0.1042(8) 1.0350(7) 0.3360(5) 0.023(2) Uani d . . . 1 . .
C C2 0.1660(8) 1.0285(6) 0.4152(5) 0.022(2) Uani d . . . 1 . .
H H2 0.2131 1.0872 0.4537 0.026 Uiso calc U . R 1 . .
C C3 0.1586(8) 0.9362(6) 0.4379(5) 0.0179(19) Uani d . . . 1 . .
C C4 0.0875(8) 0.8538(6) 0.3803(5) 0.0182(19) Uani d . . . 1 . .
H H4 0.0816 0.7892 0.3938 0.022 Uiso calc U . R 1 . .
C C5 0.0235(8) 0.8645(6) 0.3015(5) 0.0154(18) Uani d . . . 1 . .
C C6 0.1134(10) 1.1324(7) 0.3032(6) 0.035(2) Uani d . . . 1 . .
H H6A 0.183 1.1286 0.2605 0.042 Uiso calc U . R 1 . .
H H6B 0.0241 1.1358 0.2723 0.042 Uiso calc U . R 1 . .
C C7 0.1498(9) 1.2289(7) 0.3721(6) 0.026(2) Uani d . . . 1 . .
C C8 0.2784(9) 1.2849(7) 0.3769(5) 0.023(2) Uani d . . . 1 . .
H H8 0.3432 1.261 0.3376 0.027 Uiso calc U . R 1 . .
C C9 0.3116(10) 1.3740(7) 0.4379(6) 0.031(2) Uani d . . . 1 . .
H H9 0.3989 1.4116 0.4404 0.037 Uiso calc U . R 1 . .
C C10 0.2192(9) 1.4093(7) 0.4956(6) 0.027(2) Uani d . . . 1 . .
C C11 0.0913(9) 1.3565(8) 0.4933(6) 0.032(2) Uani d . . . 1 . .
H H11 0.0268 1.3812 0.5325 0.038 Uiso calc U . R 1 . .
C C12 0.0603(9) 1.2663(7) 0.4317(6) 0.030(2) Uani d . . . 1 . .
H H12 -0.0264 1.2284 0.4304 0.036 Uiso calc U . R 1 . .
C C13 0.2269(7) 0.9245(7) 0.5207(5) 0.021(2) Uani d . . . 1 . .
C C14 0.2236(8) 0.9969(7) 0.5976(6) 0.024(2) Uani d . . . 1 . .
H H14 0.1794 1.0555 0.5968 0.028 Uiso calc U . R 1 . .
C C15 0.2841(8) 0.9846(7) 0.6757(6) 0.029(2) Uani d . . . 1 . .
H H15 0.2806 1.0338 0.7281 0.034 Uiso calc U . R 1 . .
C C16 0.3493(8) 0.8998(7) 0.6755(5) 0.025(2) Uani d . . . 1 . .
C C17 0.3555(9) 0.8280(7) 0.5999(5) 0.025(2) Uani d . . . 1 . .
H H17 0.4023 0.7705 0.6004 0.03 Uiso calc U . R 1 . .
C C18 0.2930(8) 0.8406(6) 0.5236(6) 0.025(2) Uani d . . . 1 . .
H H18 0.2954 0.7904 0.4717 0.03 Uiso calc U . R 1 . .
C C19 -0.0547(8) 0.7793(6) 0.2380(5) 0.020(2) Uani d . . . 1 . .
C C20 -0.1077(8) 0.6927(7) 0.2627(6) 0.024(2) Uani d . . . 1 . .
H H20 -0.09 0.6872 0.3209 0.029 Uiso calc U . R 1 . .
C C21 -0.1870(8) 0.6133(7) 0.2025(6) 0.025(2) Uani d . . . 1 . .
H H21 -0.2224 0.5536 0.2188 0.03 Uiso calc U . R 1 . .
C C22 -0.2122(8) 0.6250(7) 0.1179(5) 0.023(2) Uani d . . . 1 . .
C C23 -0.1586(9) 0.7101(7) 0.0926(5) 0.024(2) Uani d . . . 1 . .
H H23 -0.1751 0.7158 0.0344 0.029 Uiso calc U . R 1 . .
C C24 -0.0817(9) 0.7861(7) 0.1523(5) 0.023(2) Uani d . . . 1 . .
H H24 -0.0456 0.845 0.1351 0.028 Uiso calc U . R 1 . .
C C25 0.7968(8) 0.0805(7) 1.0157(5) 0.023(2) Uani d . . . 1 . .
C C26 0.7322(8) 0.0898(7) 0.9386(5) 0.024(2) Uani d . . . 1 . .
H H26 0.6879 0.0316 0.8982 0.028 Uiso calc U . R 1 . .
C C27 0.7321(8) 0.1843(6) 0.9202(5) 0.0195(19) Uani d . . . 1 . .
C C28 0.8036(7) 0.2669(7) 0.9787(5) 0.0195(19) Uani d . . . 1 . .
H H28 0.8097 0.3319 0.9661 0.023 Uiso calc U . R 1 . .
C C29 0.8664(8) 0.2542(7) 1.0558(5) 0.020(2) Uani d . . . 1 . .
C C30 0.8044(10) -0.0177(7) 1.0433(6) 0.034(2) Uani d . . . 1 . .
H H30A 0.766 -0.0115 1.1001 0.041 Uiso calc U . R 1 . .
H H30B 0.9022 -0.0278 1.0518 0.041 Uiso calc U . R 1 . .
C C31 0.7301(8) -0.1119(7) 0.9808(5) 0.023(2) Uani d . . . 1 . .
C C32 0.7979(9) -0.1633(7) 0.9134(5) 0.026(2) Uani d . . . 1 . .
H H32 0.8884 -0.1379 0.9054 0.032 Uiso calc U . R 1 . .
C C33 0.7357(8) -0.2500(6) 0.8583(5) 0.0194(19) Uani d . . . 1 . .
H H33 0.7836 -0.2856 0.8133 0.023 Uiso calc U . R 1 . .
C C34 0.6047(9) -0.2850(7) 0.8683(6) 0.027(2) Uani d . . . 1 . .
C C35 0.5319(9) -0.2369(7) 0.9340(6) 0.030(2) Uani d . . . 1 . .
H H35 0.4407 -0.2623 0.9404 0.036 Uiso calc U . R 1 . .
C C36 0.5978(9) -0.1498(8) 0.9905(5) 0.031(2) Uani d . . . 1 . .
H H36 0.5508 -0.1156 1.0368 0.037 Uiso calc U . R 1 . .
C C37 0.6533(8) 0.1984(6) 0.8412(5) 0.020(2) Uani d . . . 1 . .
C C38 0.5926(8) 0.2830(6) 0.8427(5) 0.0141(17) Uani d . . . 1 . .
H H38 0.6034 0.334 0.895 0.017 Uiso calc U . R 1 . .
C C39 0.5151(9) 0.2997(7) 0.7722(6) 0.025(2) Uani d . . . 1 . .
H H39 0.4691 0.3585 0.7775 0.031 Uiso calc U . R 1 . .
C C40 0.5064(8) 0.2288(7) 0.6939(5) 0.023(2) Uani d . . . 1 . .
C C41 0.5696(8) 0.1415(7) 0.6896(5) 0.023(2) Uani d . . . 1 . .
H H41 0.5631 0.0915 0.6368 0.028 Uiso calc U . R 1 . .
C C42 0.6416(8) 0.1283(7) 0.7625(5) 0.022(2) Uani d . . . 1 . .
H H42 0.6852 0.0686 0.7587 0.026 Uiso calc U . R 1 . .
C C43 0.9422(8) 0.3388(6) 1.1217(5) 0.0178(19) Uani d . . . 1 . .
C C44 0.9413(8) 0.3370(7) 1.2097(5) 0.023(2) Uani d . . . 1 . .
H H44 0.8867 0.2842 1.2262 0.027 Uiso calc U . R 1 . .
C C45 1.0183(8) 0.4105(7) 1.2719(6) 0.024(2) Uani d . . . 1 . .
H H45 1.0185 0.4086 1.3313 0.028 Uiso calc U . R 1 . .
C C46 1.0966(8) 0.4882(7) 1.2469(5) 0.023(2) Uani d . . . 1 . .
C C47 1.0964(8) 0.4920(7) 1.1604(5) 0.025(2) Uani d . . . 1 . .
H H47 1.1497 0.5456 1.1442 0.03 Uiso calc U . R 1 . .
C C48 1.0183(8) 0.4174(6) 1.0979(6) 0.024(2) Uani d . . . 1 . .
H H48 1.017 0.4201 1.0386 0.028 Uiso calc U . R 1 . .
N N1 0.0354(7) 0.9537(5) 0.2798(4) 0.0221(17) Uani d . . . 1 . .
N N2 0.8608(7) 0.1615(5) 1.0744(4) 0.0236(17) Uani 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
Br1 C10 . 1.897(9) ?
Br2 C16 . 1.889(8) ?
Br3 C22 . 1.887(8) ?
Br4 C34 . 1.916(9) ?
Br5 C40 . 1.880(8) ?
Br6 C46 . 1.901(8) ?
C1 N1 . 1.349(10) ?
C1 C2 . 1.386(11) ?
C1 C6 . 1.530(12) ?
C2 C3 . 1.383(11) ?
C3 C4 . 1.377(11) ?
C3 C13 . 1.487(11) ?
C4 C5 . 1.408(10) ?
C5 N1 . 1.335(10) ?
C5 C19 . 1.471(11) ?
C6 C7 . 1.508(12) ?
C7 C12 . 1.381(13) ?
C7 C8 . 1.402(12) ?
C8 C9 . 1.372(12) ?
C9 C10 . 1.375(12) ?
C10 C11 . 1.382(13) ?
C11 C12 . 1.384(13) ?
C13 C18 . 1.380(11) ?
C13 C14 . 1.394(11) ?
C14 C15 . 1.392(11) ?
C15 C16 . 1.378(12) ?
C16 C17 . 1.379(11) ?
C17 C18 . 1.376(11) ?
C19 C20 . 1.391(12) ?
C19 C24 . 1.395(11) ?
C20 C21 . 1.406(11) ?
C21 C22 . 1.396(11) ?
C22 C23 . 1.381(12) ?
C23 C24 . 1.365(11) ?
C25 N2 . 1.348(10) ?
C25 C26 . 1.381(11) ?
C25 C30 . 1.509(12) ?
C26 C27 . 1.385(12) ?
C27 C28 . 1.386(11) ?
C27 C37 . 1.492(11) ?
C28 C29 . 1.389(10) ?
C29 N2 . 1.359(11) ?
C29 C43 . 1.476(11) ?
C30 C31 . 1.524(12) ?
C31 C36 . 1.384(12) ?
C31 C32 . 1.389(12) ?
C32 C33 . 1.367(12) ?
C33 C34 . 1.360(12) ?
C34 C35 . 1.384(12) ?
C35 C36 . 1.392(12) ?
C37 C38 . 1.348(11) ?
C37 C42 . 1.385(11) ?
C38 C39 . 1.389(11) ?
C39 C40 . 1.386(12) ?
C40 C41 . 1.388(12) ?
C41 C42 . 1.375(11) ?
C43 C48 . 1.384(12) ?
C43 C44 . 1.402(11) ?
C44 C45 . 1.368(11) ?
C45 C46 . 1.393(12) ?
C46 C47 . 1.385(11) ?
C47 C48 . 1.383(11) ?

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
N1 C1 C2 . . 122.1(8) ?
N1 C1 C6 . . 114.5(7) ?
C2 C1 C6 . . 123.4(8) ?
C3 C2 C1 . . 119.6(8) ?
C4 C3 C2 . . 117.9(7) ?
C4 C3 C13 . . 120.3(8) ?
C2 C3 C13 . . 121.8(7) ?
C3 C4 C5 . . 120.4(8) ?
N1 C5 C4 . . 120.7(7) ?
N1 C5 C19 . . 116.6(7) ?
C4 C5 C19 . . 122.8(8) ?
C7 C6 C1 . . 115.4(7) ?
C12 C7 C8 . . 117.4(8) ?
C12 C7 C6 . . 122.7(9) ?
C8 C7 C6 . . 120.0(8) ?
C9 C8 C7 . . 120.5(8) ?
C8 C9 C10 . . 120.4(9) ?
C9 C10 C11 . . 121.0(9) ?
C9 C10 Br1 . . 120.3(7) ?
C11 C10 Br1 . . 118.7(7) ?
C10 C11 C12 . . 117.7(9) ?
C7 C12 C11 . . 123.0(9) ?
C18 C13 C14 . . 118.3(8) ?
C18 C13 C3 . . 120.8(7) ?
C14 C13 C3 . . 120.9(7) ?
C15 C14 C13 . . 120.9(8) ?
C16 C15 C14 . . 118.7(8) ?
C15 C16 C17 . . 121.3(8) ?
C15 C16 Br2 . . 119.4(7) ?
C17 C16 Br2 . . 119.4(6) ?
C18 C17 C16 . . 119.2(8) ?
C17 C18 C13 . . 121.6(8) ?
C20 C19 C24 . . 118.9(8) ?
C20 C19 C5 . . 121.0(8) ?
C24 C19 C5 . . 120.1(8) ?
C19 C20 C21 . . 120.7(8) ?
C22 C21 C20 . . 117.9(8) ?
C23 C22 C21 . . 121.7(8) ?
C23 C22 Br3 . . 119.3(6) ?
C21 C22 Br3 . . 118.9(7) ?
C24 C23 C22 . . 119.2(8) ?
C23 C24 C19 . . 121.6(8) ?
N2 C25 C26 . . 121.7(8) ?
N2 C25 C30 . . 113.3(7) ?
C26 C25 C30 . . 125.0(8) ?
C25 C26 C27 . . 119.8(8) ?
C26 C27 C28 . . 118.4(7) ?
C26 C27 C37 . . 121.3(8) ?
C28 C27 C37 . . 120.3(8) ?
C27 C28 C29 . . 119.8(8) ?
N2 C29 C28 . . 121.0(8) ?
N2 C29 C43 . . 116.2(7) ?
C28 C29 C43 . . 122.8(8) ?
C25 C30 C31 . . 115.8(7) ?
C36 C31 C32 . . 118.5(9) ?
C36 C31 C30 . . 122.0(8) ?
C32 C31 C30 . . 119.4(8) ?
C33 C32 C31 . . 120.7(8) ?
C34 C33 C32 . . 119.7(8) ?
C33 C34 C35 . . 122.2(9) ?
C33 C34 Br4 . . 119.8(7) ?
C35 C34 Br4 . . 118.0(7) ?
C34 C35 C36 . . 117.3(8) ?
C31 C36 C35 . . 121.5(8) ?
C38 C37 C42 . . 116.4(8) ?
C38 C37 C27 . . 120.9(7) ?
C42 C37 C27 . . 122.7(7) ?
C37 C38 C39 . . 123.8(8) ?
C40 C39 C38 . . 118.5(8) ?
C39 C40 C41 . . 119.2(7) ?
C39 C40 Br5 . . 118.8(6) ?
C41 C40 Br5 . . 122.0(6) ?
C42 C41 C40 . . 119.3(8) ?
C41 C42 C37 . . 122.7(8) ?
C48 C43 C44 . . 119.7(8) ?
C48 C43 C29 . . 121.0(8) ?
C44 C43 C29 . . 119.2(8) ?
C45 C44 C43 . . 120.6(9) ?
C44 C45 C46 . . 119.2(8) ?
C47 C46 C45 . . 120.8(8) ?
C47 C46 Br6 . . 119.8(7) ?
C45 C46 Br6 . . 119.4(6) ?
C48 C47 C46 . . 119.7(9) ?
C47 C48 C43 . . 120.0(8) ?
C5 N1 C1 . . 119.2(7) ?
C25 N2 C29 . . 119.2(7) ?



####################################################################### 
# 
# 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_rei118
_database_code_depnum_ccdc_archive 'CCDC 1051370'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_audit_creation_date             2015-02-26
_audit_creation_method           'APEX2 v2014.9-0'
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '1(C24 H16 F3 N)'
_chemical_formula_sum            'C24 H16 F3 N'
_chemical_formula_weight         375.38
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   11.219(5)
_cell_length_b                   11.500(6)
_cell_length_c                   14.861(8)
_cell_angle_alpha                72.70(3)
_cell_angle_beta                 89.67(3)
_cell_angle_gamma                77.32(3)
_cell_volume                     1782.2(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1447
_diffrn_reflns_av_unetI/netI     0.2479
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31698
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.438
_diffrn_ambient_temperature      103.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.983
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                6610
_reflns_number_total             14348
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2014)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 2123 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1049
_refine_ls_number_reflns         14348
_refine_ls_number_restraints     596
_refine_ls_R_factor_all          0.1971
_refine_ls_R_factor_gt           0.0777
_refine_ls_restrained_S_all      0.936
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0675P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.2023
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C84-F11 \\sim C89A-F11A
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C84 \\sim C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89 \\sim F11 \\sim C84A
\\sim C85A \\sim C86A \\sim C87A \\sim C88A \\sim C89A \\sim F11A: within 1.7A
with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C84) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C87)
\\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(F11) \\sim Ueq,
Uanis(C84A) \\sim Ueq, Uanis(C85A) \\sim Ueq, Uanis(C86A) \\sim Ueq,
Uanis(C87A) \\sim Ueq, Uanis(C88A) \\sim Ueq, Uanis(C89A) \\sim Ueq,
Uanis(F11A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(C84A)=Sof(C85A)=Sof(H85A)=Sof(C86A)=Sof(H86A)=Sof(C87A)=Sof(H87A)=
 Sof(C88A)=Sof(H88A)=Sof(C89A)=Sof(F11A)=1-FVAR(1)
 Sof(C84)=Sof(C85)=Sof(H85)=Sof(C86)=Sof(H86)=Sof(C87)=Sof(H87)=Sof(C88)=
 Sof(H88)=Sof(C89)=Sof(F11)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C42(H42A,H42B), C66(H66A,H66B), C90(H90A,H90B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C28(H28),
  C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40),
 C41(H41), C45(H45), C46(H46), C47(H47), C48(H48), C50(H50), C52(H52), C56(H56),
  C57(H57), C58(H58), C59(H59), C62(H62), C63(H63), C64(H64), C65(H65),
 C69(H69), C70(H70), C71(H71), C72(H72), C74(H74), C76(H76), C80(H80), C81(H81),
  C82(H82), C83(H83), C85(H85), C86(H86), C87(H87), C88(H88), C85A(H85A),
 C86A(H86A), C87A(H87A), C88A(H88A), C93(H93), C94(H94), C95(H95), C96(H96)
6.c Fitted hexagon refined as free rotating group:
 C84(C85,C86,C87,C88,C89), C84A(C85A,C86A,C87A,C88A,C89A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.6728(5) 0.3557(5) 0.8615(5) 0.0200(16) Uani 1 1 d . U . . .
C2 C 0.5494(5) 0.4128(6) 0.8575(4) 0.0221(16) Uani 1 1 d . U . . .
H2 H 0.5217 0.4623 0.8979 0.026 Uiso 1 1 calc R . . . .
C3 C 0.4662(5) 0.3985(5) 0.7955(4) 0.0196(16) Uani 1 1 d . U . . .
C4 C 0.5115(5) 0.3249(6) 0.7366(4) 0.0193(15) Uani 1 1 d . U . . .
H4 H 0.4578 0.3133 0.6924 0.023 Uiso 1 1 calc R . . . .
C5 C 0.6345(5) 0.2700(6) 0.7440(4) 0.0206(16) Uani 1 1 d . U . . .
C6 C 0.7655(5) 0.3647(6) 0.9277(4) 0.0212(16) Uani 1 1 d . U . . .
C7 C 0.7608(5) 0.4681(6) 0.9588(5) 0.0214(16) Uani 1 1 d . U . . .
C8 C 0.8480(5) 0.4765(6) 1.0193(5) 0.0271(18) Uani 1 1 d . U . . .
H8 H 0.8423 0.5507 1.0365 0.032 Uiso 1 1 calc R . . . .
C9 C 0.9466(5) 0.3722(6) 1.0553(4) 0.0251(17) Uani 1 1 d . U . . .
H9 H 1.0066 0.3742 1.0992 0.030 Uiso 1 1 calc R . . . .
C10 C 0.9554(5) 0.2678(6) 1.0267(5) 0.0256(18) Uani 1 1 d . U . . .
H10 H 1.0232 0.1986 1.0494 0.031 Uiso 1 1 calc R . . . .
C11 C 0.8655(5) 0.2625(6) 0.9646(4) 0.0238(17) Uani 1 1 d . U . . .
H11 H 0.8718 0.1887 0.9468 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3347(5) 0.4551(5) 0.7940(5) 0.0211(16) Uani 1 1 d . U . . .
C13 C 0.2622(5) 0.5211(6) 0.7117(5) 0.0234(17) Uani 1 1 d . U . . .
C14 C 0.1403(5) 0.5750(6) 0.7076(5) 0.0330(19) Uani 1 1 d . U . . .
H14 H 0.0953 0.6187 0.6489 0.040 Uiso 1 1 calc R . . . .
C15 C 0.0838(5) 0.5635(6) 0.7939(5) 0.0350(18) Uani 1 1 d . U . . .
H15 H -0.0012 0.5983 0.7939 0.042 Uiso 1 1 calc R . . . .
C16 C 0.1509(5) 0.5025(6) 0.8769(5) 0.0353(19) Uani 1 1 d . U . . .
H16 H 0.1120 0.4975 0.9344 0.042 Uiso 1 1 calc R . . . .
C17 C 0.2755(5) 0.4469(6) 0.8802(5) 0.0313(17) Uani 1 1 d . U . . .
H17 H 0.3202 0.4041 0.9392 0.038 Uiso 1 1 calc R . . . .
C18 C 0.6912(5) 0.1903(6) 0.6826(4) 0.0235(16) Uani 1 1 d . U . . .
H18A H 0.6317 0.2014 0.6301 0.028 Uiso 1 1 calc R . . . .
H18B H 0.7644 0.2184 0.6550 0.028 Uiso 1 1 calc R . . . .
C19 C 0.7275(5) 0.0539(6) 0.7393(5) 0.0221(16) Uani 1 1 d . U . . .
C20 C 0.6710(5) -0.0339(6) 0.7257(5) 0.0239(17) Uani 1 1 d . U . . .
C21 C 0.7032(5) -0.1597(6) 0.7744(5) 0.0291(18) Uani 1 1 d . U . . .
H21 H 0.6617 -0.2165 0.7604 0.035 Uiso 1 1 calc R . . . .
C22 C 0.7963(5) -0.2009(6) 0.8435(5) 0.0288(19) Uani 1 1 d . U . . .
H22 H 0.8204 -0.2871 0.8783 0.035 Uiso 1 1 calc R . . . .
C23 C 0.8546(5) -0.1160(6) 0.8619(5) 0.0280(18) Uani 1 1 d . U . . .
H23 H 0.9173 -0.1437 0.9112 0.034 Uiso 1 1 calc R . . . .
C24 C 0.8235(5) 0.0076(6) 0.8102(5) 0.0269(18) Uani 1 1 d . U . . .
H24 H 0.8677 0.0636 0.8225 0.032 Uiso 1 1 calc R . . . .
C25 C 0.7609(5) 0.0023(6) 0.4375(4) 0.0192(16) Uani 1 1 d . U . . .
C26 C 0.6658(5) -0.0593(5) 0.4634(5) 0.0209(16) Uani 1 1 d . U . . .
H26 H 0.6637 -0.1104 0.5264 0.025 Uiso 1 1 calc R . . . .
C27 C 0.5749(5) -0.0449(5) 0.3962(4) 0.0177(15) Uani 1 1 d . U . . .
C28 C 0.5842(5) 0.0297(5) 0.3010(4) 0.0171(15) Uani 1 1 d . U . . .
H28 H 0.5245 0.0402 0.2524 0.020 Uiso 1 1 calc R . . . .
C29 C 0.6818(5) 0.0857(5) 0.2823(4) 0.0172(15) Uani 1 1 d . U . . .
C30 C 0.8575(5) -0.0003(5) 0.5083(4) 0.0180(15) Uani 1 1 d . U . . .
C31 C 0.9079(5) -0.1026(5) 0.5840(4) 0.0194(15) Uani 1 1 d . U . . .
C32 C 0.9981(5) -0.1019(6) 0.6467(5) 0.0256(17) Uani 1 1 d . U . . .
H32 H 1.0311 -0.1748 0.6977 0.031 Uiso 1 1 calc R . . . .
C33 C 1.0390(5) 0.0044(6) 0.6345(5) 0.0270(18) Uani 1 1 d . U . . .
H33 H 1.0997 0.0066 0.6778 0.032 Uiso 1 1 calc R . . . .
C34 C 0.9918(5) 0.1095(6) 0.5588(5) 0.0264(18) Uani 1 1 d . U . . .
H34 H 1.0213 0.1833 0.5495 0.032 Uiso 1 1 calc R . . . .
C35 C 0.9010(5) 0.1068(6) 0.4962(4) 0.0224(17) Uani 1 1 d . U . . .
H35 H 0.8686 0.1792 0.4447 0.027 Uiso 1 1 calc R . . . .
C36 C 0.4698(5) -0.1008(5) 0.4217(4) 0.0169(15) Uani 1 1 d . U . . .
C37 C 0.4205(5) -0.1623(6) 0.3680(5) 0.0220(16) Uani 1 1 d . U . . .
C38 C 0.3206(5) -0.2126(6) 0.3910(5) 0.0234(17) Uani 1 1 d . U . . .
H38 H 0.2903 -0.2530 0.3518 0.028 Uiso 1 1 calc R . . . .
C39 C 0.2644(5) -0.2034(6) 0.4729(5) 0.0294(18) Uani 1 1 d . U . . .
H39 H 0.1950 -0.2379 0.4901 0.035 Uiso 1 1 calc R . . . .
C40 C 0.3087(6) -0.1442(6) 0.5298(5) 0.0330(19) Uani 1 1 d . U . . .
H40 H 0.2695 -0.1375 0.5854 0.040 Uiso 1 1 calc R . . . .
C41 C 0.4105(5) -0.0949(6) 0.5049(5) 0.0240(17) Uani 1 1 d . U . . .
H41 H 0.4414 -0.0560 0.5450 0.029 Uiso 1 1 calc R . . . .
C42 C 0.6956(5) 0.1695(6) 0.1843(4) 0.0198(16) Uani 1 1 d . U . . .
H42A H 0.7803 0.1456 0.1660 0.024 Uiso 1 1 calc R . . . .
H42B H 0.6393 0.1581 0.1382 0.024 Uiso 1 1 calc R . . . .
C43 C 0.6673(5) 0.3045(6) 0.1818(4) 0.0204(16) Uani 1 1 d . U . . .
C44 C 0.5653(5) 0.3896(6) 0.1308(4) 0.0207(16) Uani 1 1 d . U . . .
C45 C 0.5324(5) 0.5144(6) 0.1266(5) 0.0239(17) Uani 1 1 d . U . . .
H45 H 0.4620 0.5690 0.0897 0.029 Uiso 1 1 calc R . . . .
C46 C 0.6058(5) 0.5563(6) 0.1781(5) 0.0284(18) Uani 1 1 d . U . . .
H46 H 0.5857 0.6412 0.1775 0.034 Uiso 1 1 calc R . . . .
C47 C 0.7088(5) 0.4752(6) 0.2306(5) 0.0259(17) Uani 1 1 d . U . . .
H47 H 0.7583 0.5044 0.2668 0.031 Uiso 1 1 calc R . . . .
C48 C 0.7399(5) 0.3515(6) 0.2306(4) 0.0237(17) Uani 1 1 d . U . . .
H48 H 0.8127 0.2980 0.2648 0.028 Uiso 1 1 calc R . . . .
C49 C 0.1728(5) 0.3565(5) 0.5732(4) 0.0176(15) Uani 1 1 d . U . . .
C50 C 0.0512(5) 0.4190(5) 0.5503(5) 0.0195(16) Uani 1 1 d . U . . .
H50 H 0.0251 0.4711 0.4878 0.023 Uiso 1 1 calc R . . . .
C51 C -0.0318(5) 0.4042(5) 0.6202(4) 0.0179(16) Uani 1 1 d . U . . .
C52 C 0.0102(5) 0.3240(5) 0.7109(5) 0.0214(17) Uani 1 1 d . U . . .
H52 H -0.0448 0.3104 0.7599 0.026 Uiso 1 1 calc R . . . .
C53 C 0.1326(5) 0.2651(5) 0.7278(4) 0.0199(16) Uani 1 1 d . U . . .
C54 C 0.2681(5) 0.3611(6) 0.5018(4) 0.0206(15) Uani 1 1 d . U . . .
C55 C 0.2677(5) 0.4652(6) 0.4229(5) 0.0218(16) Uani 1 1 d . U . . .
C56 C 0.3564(5) 0.4690(6) 0.3584(4) 0.0237(17) Uani 1 1 d . U . . .
H56 H 0.3516 0.5417 0.3059 0.028 Uiso 1 1 calc R . . . .
C57 C 0.4530(5) 0.3655(6) 0.3708(5) 0.0244(18) Uani 1 1 d . U . . .
H57 H 0.5152 0.3665 0.3271 0.029 Uiso 1 1 calc R . . . .
C58 C 0.4574(5) 0.2601(6) 0.4485(5) 0.0283(18) Uani 1 1 d . U . . .
H58 H 0.5233 0.1890 0.4575 0.034 Uiso 1 1 calc R . . . .
C59 C 0.3677(5) 0.2574(6) 0.5124(4) 0.0223(17) Uani 1 1 d . U . . .
H59 H 0.3730 0.1844 0.5647 0.027 Uiso 1 1 calc R . . . .
C60 C -0.1619(5) 0.4665(6) 0.5935(4) 0.0217(16) Uani 1 1 d . U . . .
C61 C -0.2349(5) 0.5313(5) 0.6484(4) 0.0206(16) Uani 1 1 d . U . . .
C62 C -0.3579(5) 0.5882(6) 0.6279(5) 0.0284(18) Uani 1 1 d . U . . .
H62 H -0.4029 0.6321 0.6668 0.034 Uiso 1 1 calc R . . . .
C63 C -0.4126(6) 0.5780(6) 0.5474(5) 0.0326(19) Uani 1 1 d . U . . .
H63 H -0.4974 0.6139 0.5321 0.039 Uiso 1 1 calc R . . . .
C64 C -0.3476(5) 0.5177(6) 0.4900(5) 0.0296(18) Uani 1 1 d . U . . .
H64 H -0.3870 0.5128 0.4353 0.035 Uiso 1 1 calc R . . . .
C65 C -0.2221(5) 0.4629(6) 0.5119(5) 0.0280(18) Uani 1 1 d . U . . .
H65 H -0.1771 0.4227 0.4708 0.034 Uiso 1 1 calc R . . . .
C66 C 0.1861(5) 0.1802(6) 0.8265(4) 0.0232(17) Uani 1 1 d . U . . .
H66A H 0.2574 0.2080 0.8447 0.028 Uiso 1 1 calc R . . . .
H66B H 0.1238 0.1879 0.8731 0.028 Uiso 1 1 calc R . . . .
C67 C 0.2257(5) 0.0453(6) 0.8290(4) 0.0197(16) Uani 1 1 d . U . . .
C68 C 0.1691(5) -0.0452(6) 0.8816(5) 0.0262(17) Uani 1 1 d . U . . .
C69 C 0.1975(5) -0.1671(6) 0.8833(5) 0.0298(18) Uani 1 1 d . U . . .
H69 H 0.1531 -0.2243 0.9198 0.036 Uiso 1 1 calc R . . . .
C70 C 0.2910(5) -0.2063(6) 0.8316(5) 0.0277(18) Uani 1 1 d . U . . .
H70 H 0.3118 -0.2911 0.8317 0.033 Uiso 1 1 calc R . . . .
C71 C 0.3552(5) -0.1211(6) 0.7788(5) 0.0262(18) Uani 1 1 d . U . . .
H71 H 0.4207 -0.1474 0.7432 0.031 Uiso 1 1 calc R . . . .
C72 C 0.3226(5) 0.0021(6) 0.7787(5) 0.0241(17) Uani 1 1 d . U . . .
H72 H 0.3675 0.0595 0.7432 0.029 Uiso 1 1 calc R . . . .
C73 C 0.2512(5) 0.0007(6) 0.1511(4) 0.0188(15) Uani 1 1 d . U . . .
C74 C 0.1572(5) -0.0601(6) 0.1583(4) 0.0217(16) Uani 1 1 d . U . . .
H74 H 0.1532 -0.1123 0.1200 0.026 Uiso 1 1 calc R . . . .
C75 C 0.0682(5) -0.0447(6) 0.2216(4) 0.0193(15) Uani 1 1 d . U . . .
C76 C 0.0771(5) 0.0333(5) 0.2769(4) 0.0192(15) Uani 1 1 d . U . . .
H76 H 0.0182 0.0456 0.3214 0.023 Uiso 1 1 calc R . . . .
C77 C 0.1739(5) 0.0919(5) 0.2648(4) 0.0205(15) Uani 1 1 d . U . . .
C78 C 0.3508(5) -0.0113(6) 0.0832(4) 0.0207(16) Uani 1 1 d . U . . .
C79 C 0.3962(5) -0.1159(6) 0.0575(4) 0.0220(16) Uani 1 1 d . U . . .
C80 C 0.4913(6) -0.1293(6) -0.0007(5) 0.0280(18) Uani 1 1 d . U . . .
H80 H 0.5210 -0.2054 -0.0148 0.034 Uiso 1 1 calc R . . . .
C81 C 0.5413(5) -0.0264(6) -0.0375(5) 0.0266(18) Uani 1 1 d . U . . .
H81 H 0.6056 -0.0312 -0.0791 0.032 Uiso 1 1 calc R . . . .
C82 C 0.4998(5) 0.0816(6) -0.0152(5) 0.0312(19) Uani 1 1 d . U . . .
H82 H 0.5351 0.1514 -0.0410 0.037 Uiso 1 1 calc R . . . .
C83 C 0.4051(5) 0.0894(6) 0.0459(5) 0.0241(17) Uani 1 1 d . U . . .
H83 H 0.3774 0.1644 0.0621 0.029 Uiso 1 1 calc R . . . .
C84 C -0.0955(5) -0.1014(6) 0.1434(4) 0.0247(13) Uani 0.459(5) 1 d D U P A 1
C85 C -0.1965(6) -0.1538(8) 0.1467(5) 0.0255(15) Uani 0.459(5) 1 d G U P A 1
H85 H -0.2397 -0.1466 0.0898 0.031 Uiso 0.459(5) 1 calc R . P A 1
C86 C -0.2343(7) -0.2167(9) 0.2332(6) 0.0247(15) Uani 0.459(5) 1 d G U P A 1
H86 H -0.3034 -0.2525 0.2354 0.030 Uiso 0.459(5) 1 calc R . P A 1
C87 C -0.1711(8) -0.2272(9) 0.3164(5) 0.0239(14) Uani 0.459(5) 1 d G U P A 1
H87 H -0.1970 -0.2702 0.3756 0.029 Uiso 0.459(5) 1 calc R . P A 1
C88 C -0.0700(7) -0.1749(9) 0.3132(4) 0.0224(13) Uani 0.459(5) 1 d G U P A 1
H88 H -0.0268 -0.1821 0.3701 0.027 Uiso 0.459(5) 1 calc R . P A 1
C89 C -0.0322(6) -0.1120(7) 0.2266(5) 0.0236(13) Uani 0.459(5) 1 d G U P A 1
F11 F -0.0904(7) -0.0493(8) 0.0740(6) 0.038(2) Uani 0.459(5) 1 d D U P A 1
C84A C -0.0337(4) -0.1157(5) 0.2384(4) 0.0228(13) Uani 0.541(5) 1 d . U P A 2
C85A C -0.1077(5) -0.1136(6) 0.1629(4) 0.0239(13) Uani 0.541(5) 1 d G U P A 2
H85A H -0.0926 -0.0707 0.1002 0.029 Uiso 0.541(5) 1 calc R . P A 2
C86A C -0.2038(6) -0.1742(8) 0.1793(5) 0.0236(13) Uani 0.541(5) 1 d G U P A 2
H86A H -0.2543 -0.1727 0.1278 0.028 Uiso 0.541(5) 1 calc R . P A 2
C87A C -0.2259(6) -0.2369(7) 0.2711(6) 0.0245(15) Uani 0.541(5) 1 d G U P A 2
H87A H -0.2915 -0.2783 0.2823 0.029 Uiso 0.541(5) 1 calc R . P A 2
C88A C -0.1519(6) -0.2390(7) 0.3466(5) 0.0228(14) Uani 0.541(5) 1 d G U P A 2
H88A H -0.1670 -0.2819 0.4093 0.027 Uiso 0.541(5) 1 calc R . P A 2
C89A C -0.0558(5) -0.1784(6) 0.3302(4) 0.0240(13) Uani 0.541(5) 1 d DG U P A 2
F11A F -0.0030(4) -0.1836(5) 0.3945(4) 0.0178(15) Uani 0.541(5) 1 d D U P A 2
C90 C 0.1889(5) 0.1779(5) 0.3223(4) 0.0228(16) Uani 1 1 d . U . . .
H90A H 0.1325 0.1680 0.3741 0.027 Uiso 1 1 calc R . . . .
H90B H 0.2736 0.1524 0.3512 0.027 Uiso 1 1 calc R . . . .
C91 C 0.1636(5) 0.3137(5) 0.2640(4) 0.0205(16) Uani 1 1 d . U . . .
C92 C 0.0673(5) 0.4011(6) 0.2792(4) 0.0222(16) Uani 1 1 d . U . . .
C93 C 0.0389(5) 0.5250(6) 0.2289(5) 0.0250(17) Uani 1 1 d . U . . .
H93 H -0.0293 0.5802 0.2435 0.030 Uiso 1 1 calc R . . . .
C94 C 0.1113(5) 0.5694(6) 0.1557(5) 0.0271(18) Uani 1 1 d . U . . .
H94 H 0.0938 0.6554 0.1198 0.032 Uiso 1 1 calc R . . . .
C95 C 0.2094(5) 0.4854(6) 0.1364(5) 0.0283(18) Uani 1 1 d . U . . .
H95 H 0.2592 0.5136 0.0863 0.034 Uiso 1 1 calc R . . . .
C96 C 0.2356(5) 0.3592(6) 0.1905(4) 0.0234(17) Uani 1 1 d . U . . .
H96 H 0.3039 0.3031 0.1768 0.028 Uiso 1 1 calc R . . . .
F1 F 0.6673(3) 0.5707(3) 0.9235(3) 0.0271(10) Uani 1 1 d . U . . .
F2 F 0.3142(4) 0.5307(4) 0.6285(3) 0.0470(13) Uani 1 1 d . U . . .
F3 F 0.5767(3) 0.0056(3) 0.6557(3) 0.0324(10) Uani 1 1 d . U . . .
F4 F 0.8724(3) -0.2112(3) 0.5969(3) 0.0291(10) Uani 1 1 d . U . . .
F5 F 0.4763(3) -0.1754(3) 0.2885(3) 0.0314(10) Uani 1 1 d . U . . .
F6 F 0.4902(3) 0.3497(3) 0.0798(2) 0.0255(10) Uani 1 1 d . U . . .
F7 F 0.1763(3) 0.5701(3) 0.4103(3) 0.0267(10) Uani 1 1 d . U . . .
F8 F -0.1830(3) 0.5416(3) 0.7275(3) 0.0326(11) Uani 1 1 d . U . . .
F9 F 0.0732(3) -0.0096(3) 0.9338(3) 0.0312(11) Uani 1 1 d . U . . .
F10 F 0.3505(3) -0.2208(3) 0.0961(3) 0.0284(10) Uani 1 1 d . U . . .
F12 F -0.0074(3) 0.3616(3) 0.3519(3) 0.0301(10) Uani 1 1 d . U . . .
N1 N 0.7154(4) 0.2841(4) 0.8046(4) 0.0187(13) Uani 1 1 d . U . . .
N2 N 0.7682(4) 0.0747(4) 0.3493(3) 0.0180(13) Uani 1 1 d . U . . .
N3 N 0.2142(4) 0.2791(5) 0.6617(4) 0.0211(13) Uani 1 1 d . U . . .
N4 N 0.2602(4) 0.0772(5) 0.2030(4) 0.0217(14) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(8) . ?
C1 C6 1.477(9) . ?
C1 N1 1.362(8) . ?
C2 C3 1.383(9) . ?
C3 C4 1.411(9) . ?
C3 C12 1.474(8) . ?
C4 C5 1.376(7) . ?
C5 C18 1.521(9) . ?
C5 N1 1.350(8) . ?
C6 C7 1.389(9) . ?
C6 C11 1.409(8) . ?
C7 C8 1.371(9) . ?
C7 F1 1.365(6) . ?
C8 C9 1.411(8) . ?
C9 C10 1.372(10) . ?
C10 C11 1.394(9) . ?
C12 C13 1.387(8) . ?
C12 C17 1.426(9) . ?
C13 C14 1.365(8) . ?
C13 F2 1.349(8) . ?
C14 C15 1.410(10) . ?
C15 C16 1.357(9) . ?
C16 C17 1.399(8) . ?
C18 C19 1.508(8) . ?
C19 C20 1.366(9) . ?
C19 C24 1.409(8) . ?
C20 C21 1.377(8) . ?
C20 F3 1.389(7) . ?
C21 C22 1.369(9) . ?
C22 C23 1.378(10) . ?
C23 C24 1.366(9) . ?
C25 C26 1.397(8) . ?
C25 C30 1.504(8) . ?
C25 N2 1.341(7) . ?
C26 C27 1.379(8) . ?
C27 C28 1.436(8) . ?
C27 C36 1.460(8) . ?
C28 C29 1.375(8) . ?
C29 C42 1.518(8) . ?
C29 N2 1.352(7) . ?
C30 C31 1.378(8) . ?
C30 C35 1.385(9) . ?
C31 C32 1.382(9) . ?
C31 F4 1.352(7) . ?
C32 C33 1.361(9) . ?
C33 C34 1.388(8) . ?
C34 C35 1.395(9) . ?
C36 C37 1.399(9) . ?
C36 C41 1.413(9) . ?
C37 C38 1.368(8) . ?
C37 F5 1.366(8) . ?
C38 C39 1.390(10) . ?
C39 C40 1.384(11) . ?
C40 C41 1.385(9) . ?
C42 C43 1.504(9) . ?
C43 C44 1.385(7) . ?
C43 C48 1.384(9) . ?
C44 C45 1.383(9) . ?
C44 F6 1.371(7) . ?
C45 C46 1.377(10) . ?
C46 C47 1.385(8) . ?
C47 C48 1.388(9) . ?
C49 C50 1.386(7) . ?
C49 C54 1.500(9) . ?
C49 N3 1.366(7) . ?
C50 C51 1.389(8) . ?
C51 C52 1.402(8) . ?
C51 C60 1.477(7) . ?
C52 C53 1.380(8) . ?
C53 C66 1.538(8) . ?
C53 N3 1.338(8) . ?
C54 C55 1.404(8) . ?
C54 C59 1.414(8) . ?
C55 C56 1.376(9) . ?
C55 F7 1.367(6) . ?
C56 C57 1.390(8) . ?
C57 C58 1.395(9) . ?
C58 C59 1.379(9) . ?
C60 C61 1.406(9) . ?
C60 C65 1.408(9) . ?
C61 C62 1.383(8) . ?
C61 F8 1.364(7) . ?
C62 C63 1.396(10) . ?
C63 C64 1.364(10) . ?
C64 C65 1.407(8) . ?
C66 C67 1.506(9) . ?
C67 C68 1.377(9) . ?
C67 C72 1.401(9) . ?
C68 C69 1.360(9) . ?
C68 F9 1.383(7) . ?
C69 C70 1.373(9) . ?
C70 C71 1.393(9) . ?
C71 C72 1.383(9) . ?
C73 C74 1.375(9) . ?
C73 C78 1.512(8) . ?
C73 N4 1.351(9) . ?
C74 C75 1.387(9) . ?
C75 C76 1.403(9) . ?
C75 C89 1.490(9) . ?
C75 C84A 1.524(8) . ?
C76 C77 1.383(9) . ?
C77 C90 1.521(9) . ?
C77 N4 1.349(8) . ?
C78 C79 1.362(9) . ?
C78 C83 1.394(9) . ?
C79 C80 1.381(9) . ?
C79 F10 1.380(7) . ?
C80 C81 1.384(9) . ?
C81 C82 1.364(10) . ?
C82 C83 1.398(9) . ?
C84 C85 1.3900 . ?
C84 C89 1.3900 . ?
C84 F11 1.035(9) . ?
C85 C86 1.3900 . ?
C86 C87 1.3900 . ?
C87 C88 1.3900 . ?
C88 C89 1.3900 . ?
C84A C85A 1.3900 . ?
C84A C89A 1.3900 . ?
C85A C86A 1.3900 . ?
C86A C87A 1.3900 . ?
C87A C88A 1.3900 . ?
C88A C89A 1.3900 . ?
C89A F11A 1.107(8) . ?
C90 C91 1.508(8) . ?
C91 C92 1.372(8) . ?
C91 C96 1.398(9) . ?
C92 C93 1.364(8) . ?
C92 F12 1.394(7) . ?
C93 C94 1.395(9) . ?
C94 C95 1.386(9) . ?
C95 C96 1.399(8) . ?

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
C2 C1 C6 123.4(6) . . ?
N1 C1 C2 121.1(6) . . ?
N1 C1 C6 115.5(5) . . ?
C3 C2 C1 120.8(6) . . ?
C2 C3 C4 117.6(5) . . ?
C2 C3 C12 120.7(6) . . ?
C4 C3 C12 121.6(6) . . ?
C5 C4 C3 119.0(6) . . ?
C4 C5 C18 122.5(6) . . ?
N1 C5 C4 123.2(6) . . ?
N1 C5 C18 114.3(5) . . ?
C7 C6 C1 124.3(5) . . ?
C7 C6 C11 116.1(6) . . ?
C11 C6 C1 119.5(6) . . ?
C8 C7 C6 124.1(5) . . ?
F1 C7 C6 118.5(5) . . ?
F1 C7 C8 117.4(6) . . ?
C7 C8 C9 118.2(6) . . ?
C10 C9 C8 119.9(6) . . ?
C9 C10 C11 120.4(6) . . ?
C10 C11 C6 121.2(7) . . ?
C13 C12 C3 123.5(6) . . ?
C13 C12 C17 116.1(5) . . ?
C17 C12 C3 120.4(5) . . ?
C14 C13 C12 125.1(6) . . ?
F2 C13 C12 118.1(5) . . ?
F2 C13 C14 116.7(6) . . ?
C13 C14 C15 117.5(6) . . ?
C16 C15 C14 120.0(6) . . ?
C15 C16 C17 122.0(7) . . ?
C16 C17 C12 119.3(6) . . ?
C19 C18 C5 111.1(5) . . ?
C20 C19 C18 123.0(5) . . ?
C20 C19 C24 115.0(5) . . ?
C24 C19 C18 122.0(6) . . ?
C19 C20 C21 124.7(6) . . ?
C19 C20 F3 117.7(5) . . ?
C21 C20 F3 117.5(6) . . ?
C22 C21 C20 118.5(6) . . ?
C21 C22 C23 119.2(6) . . ?
C24 C23 C22 121.0(6) . . ?
C23 C24 C19 121.4(6) . . ?
C26 C25 C30 122.2(5) . . ?
N2 C25 C26 122.6(5) . . ?
N2 C25 C30 115.0(5) . . ?
C27 C26 C25 119.2(6) . . ?
C26 C27 C28 118.5(5) . . ?
C26 C27 C36 120.8(5) . . ?
C28 C27 C36 120.7(5) . . ?
C29 C28 C27 118.0(5) . . ?
C28 C29 C42 121.1(5) . . ?
N2 C29 C28 123.2(5) . . ?
N2 C29 C42 115.7(5) . . ?
C31 C30 C25 124.7(6) . . ?
C31 C30 C35 117.1(5) . . ?
C35 C30 C25 118.2(5) . . ?
C30 C31 C32 123.0(6) . . ?
F4 C31 C30 119.6(5) . . ?
F4 C31 C32 117.3(5) . . ?
C33 C32 C31 119.2(6) . . ?
C32 C33 C34 119.9(6) . . ?
C33 C34 C35 120.0(6) . . ?
C30 C35 C34 120.8(5) . . ?
C37 C36 C27 124.0(6) . . ?
C37 C36 C41 115.5(5) . . ?
C41 C36 C27 120.5(6) . . ?
C38 C37 C36 124.0(6) . . ?
F5 C37 C36 118.4(5) . . ?
F5 C37 C38 117.5(6) . . ?
C37 C38 C39 118.5(7) . . ?
C40 C39 C38 120.6(6) . . ?
C39 C40 C41 119.6(7) . . ?
C40 C41 C36 121.8(7) . . ?
C43 C42 C29 110.7(5) . . ?
C44 C43 C42 121.6(6) . . ?
C48 C43 C42 122.6(5) . . ?
C48 C43 C44 115.8(6) . . ?
C45 C44 C43 124.8(6) . . ?
F6 C44 C43 118.8(6) . . ?
F6 C44 C45 116.4(5) . . ?
C46 C45 C44 117.4(5) . . ?
C45 C46 C47 120.3(6) . . ?
C46 C47 C48 120.2(6) . . ?
C43 C48 C47 121.5(5) . . ?
C50 C49 C54 123.0(5) . . ?
N3 C49 C50 122.6(5) . . ?
N3 C49 C54 114.3(4) . . ?
C49 C50 C51 118.9(5) . . ?
C50 C51 C52 118.6(5) . . ?
C50 C51 C60 118.2(5) . . ?
C52 C51 C60 123.1(5) . . ?
C53 C52 C51 118.8(6) . . ?
C52 C53 C66 121.7(6) . . ?
N3 C53 C52 123.4(5) . . ?
N3 C53 C66 114.8(5) . . ?
C55 C54 C49 124.1(5) . . ?
C55 C54 C59 115.6(5) . . ?
C59 C54 C49 120.3(5) . . ?
C56 C55 C54 123.6(5) . . ?
F7 C55 C54 118.5(5) . . ?
F7 C55 C56 117.8(5) . . ?
C55 C56 C57 119.3(6) . . ?
C56 C57 C58 119.0(6) . . ?
C59 C58 C57 121.0(6) . . ?
C58 C59 C54 121.4(6) . . ?
C61 C60 C51 122.6(6) . . ?
C61 C60 C65 115.3(5) . . ?
C65 C60 C51 122.0(6) . . ?
C62 C61 C60 124.9(6) . . ?
F8 C61 C60 119.0(5) . . ?
F8 C61 C62 116.0(6) . . ?
C61 C62 C63 116.7(6) . . ?
C64 C63 C62 121.8(6) . . ?
C63 C64 C65 120.0(7) . . ?
C64 C65 C60 121.2(7) . . ?
C67 C66 C53 111.6(6) . . ?
C68 C67 C66 122.2(6) . . ?
C68 C67 C72 115.0(6) . . ?
C72 C67 C66 122.8(5) . . ?
C67 C68 F9 118.2(6) . . ?
C69 C68 C67 124.7(6) . . ?
C69 C68 F9 117.1(6) . . ?
C68 C69 C70 119.1(6) . . ?
C69 C70 C71 119.6(6) . . ?
C72 C71 C70 119.3(6) . . ?
C71 C72 C67 122.3(6) . . ?
C74 C73 C78 122.5(6) . . ?
N4 C73 C74 122.4(6) . . ?
N4 C73 C78 115.1(5) . . ?
C73 C74 C75 119.8(6) . . ?
C74 C75 C76 118.5(6) . . ?
C74 C75 C89 117.8(6) . . ?
C74 C75 C84A 122.7(6) . . ?
C76 C75 C89 123.7(6) . . ?
C76 C75 C84A 118.6(5) . . ?
C77 C76 C75 118.2(6) . . ?
C76 C77 C90 120.9(6) . . ?
N4 C77 C76 123.2(6) . . ?
N4 C77 C90 115.8(5) . . ?
C79 C78 C73 125.0(6) . . ?
C79 C78 C83 116.2(6) . . ?
C83 C78 C73 118.8(6) . . ?
C78 C79 C80 125.1(6) . . ?
C78 C79 F10 118.8(5) . . ?
F10 C79 C80 115.9(6) . . ?
C79 C80 C81 116.8(7) . . ?
C82 C81 C80 121.1(6) . . ?
C81 C82 C83 119.8(6) . . ?
C78 C83 C82 120.9(6) . . ?
C85 C84 C89 120.0 . . ?
F11 C84 C85 107.5(6) . . ?
F11 C84 C89 132.0(7) . . ?
C86 C85 C84 120.0 . . ?
C85 C86 C87 120.0 . . ?
C88 C87 C86 120.0 . . ?
C87 C88 C89 120.0 . . ?
C84 C89 C75 118.9(4) . . ?
C88 C89 C75 120.9(4) . . ?
C88 C89 C84 120.0 . . ?
C85A C84A C75 120.4(4) . . ?
C85A C84A C89A 120.0 . . ?
C89A C84A C75 119.5(4) . . ?
C84A C85A C86A 120.0 . . ?
C85A C86A C87A 120.0 . . ?
C86A C87A C88A 120.0 . . ?
C89A C88A C87A 120.0 . . ?
C88A C89A C84A 120.0 . . ?
F11A C89A C84A 125.1(5) . . ?
F11A C89A C88A 114.9(5) . . ?
C91 C90 C77 112.8(5) . . ?
C92 C91 C90 122.1(6) . . ?
C92 C91 C96 115.4(5) . . ?
C96 C91 C90 122.5(5) . . ?
C91 C92 F12 118.1(5) . . ?
C93 C92 C91 125.1(6) . . ?
C93 C92 F12 116.8(5) . . ?
C92 C93 C94 119.1(6) . . ?
C95 C94 C93 118.5(6) . . ?
C94 C95 C96 120.4(6) . . ?
C91 C96 C95 121.6(6) . . ?
C5 N1 C1 118.3(5) . . ?
C25 N2 C29 118.5(5) . . ?
C53 N3 C49 117.6(5) . . ?
C77 N4 C73 117.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 1051371'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 F3 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         449.45

_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                   17.8858(12)
_cell_length_b                   5.3984(4)
_cell_length_c                   24.0688(17)
_cell_angle_alpha                90
_cell_angle_beta                 107.814(2)
_cell_angle_gamma                90
_cell_volume                     2212.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2120
_cell_measurement_theta_min      3.2399
_cell_measurement_theta_max      21.6106
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            35846
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32

_refine_special_details          
;
;

_reflns_number_total             5465
_reflns_number_gt                3170
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1793
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         5465
_refine_ls_number_parameters     329
_refine_ls_number_restraints     102
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²+0.7470P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0052(11)

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'
O O 0.0106 0.0060 '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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

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 0.91553(14) 0.6128(5) 0.17372(11) 0.0346(6) Uani d . . . 1.0 . .
H H1A 0.9696 0.6159 0.1999 0.052 Uiso calc U . R 1.0 . .
H H1B 0.9159 0.6298 0.1333 0.052 Uiso calc U . R 1.0 . .
H H1C 0.8908 0.4554 0.1783 0.052 Uiso calc U . R 1.0 . .
C C2 0.86645(12) 0.8211(4) 0.24334(9) 0.0221(5) Uani d . . . 1.0 . .
C C3 0.89693(12) 0.6453(4) 0.28605(10) 0.0238(5) Uani d . . . 1.0 . .
H H3 0.924 0.505 0.278 0.029 Uiso calc U . R 1.0 . .
C C4 0.88763(12) 0.6757(4) 0.34081(9) 0.0232(5) Uani d . . . 1.0 . .
H H4 0.9077 0.5527 0.3697 0.028 Uiso calc U . R 1.0 . .
C C5 0.84977(12) 0.8812(4) 0.35462(9) 0.0203(5) Uani d . . . 1.0 . .
C C6 0.81935(12) 1.0548(4) 0.31052(9) 0.0221(5) Uani d . . . 1.0 . .
H H6 0.7929 1.1964 0.3186 0.026 Uiso calc U . R 1.0 . .
C C7 0.82671(12) 1.0261(4) 0.25561(9) 0.0221(5) Uani d . . . 1.0 . .
H H7 0.8048 1.1456 0.2262 0.027 Uiso calc U . R 1.0 . .
C C8 0.84245(12) 0.9155(4) 0.41414(9) 0.0215(5) Uani d . . . 1.0 . .
C C9 0.78805(12) 1.0800(4) 0.42417(9) 0.0230(5) Uani d . . . 1.0 . .
H H9 0.7546 1.1721 0.3926 0.028 Uiso calc U . R 1.0 . .
C C10 0.78239(12) 1.1101(4) 0.47994(9) 0.0246(5) Uani d . . . 1.0 . .
C C11 0.83162(12) 0.9758(4) 0.52479(9) 0.0247(5) Uani d . . . 1.0 . .
H H11 0.8298 0.9961 0.5635 0.03 Uiso calc U . R 1.0 . .
C C12 0.88326(13) 0.8128(5) 0.51323(10) 0.0298(5) Uani d . . . 1.0 . .
C C13 0.93826(15) 0.6602(6) 0.56124(11) 0.0441(7) Uani d . . . 1.0 . .
H H13A 0.9332 0.4841 0.5492 0.053 Uiso calc U . R 1.0 . .
H H13B 0.9929 0.7119 0.5657 0.053 Uiso calc U . R 1.0 . .
C C14 0.92415(14) 0.6810(5) 0.61971(10) 0.0338(6) Uani d . . . 1.0 . .
C C15 0.87345(18) 0.5205(6) 0.63496(12) 0.0553(8) Uani d . . . 1.0 . .
H H15 0.8491 0.3911 0.609 0.066 Uiso calc U . R 1.0 . .
C C16 0.85764(18) 0.5451(6) 0.68735(12) 0.0555(9) Uani d . . . 1.0 . .
H H16 0.8228 0.4327 0.6971 0.067 Uiso calc U . R 1.0 . .
C C17 0.89224(15) 0.7320(5) 0.72543(10) 0.0348(6) Uani d . . . 1.0 . .
C C18 0.87635(18) 0.7674(6) 0.78170(12) 0.0502(7) Uani d U . D 1.0 . .
C C19 0.94483(14) 0.8872(5) 0.71165(12) 0.0401(7) Uani d . . . 1.0 . .
H H19 0.9706 1.0126 0.7384 0.048 Uiso calc U . R 1.0 . .
C C20 0.96039(14) 0.8621(5) 0.65926(12) 0.0380(6) Uani d . . . 1.0 . .
H H20 0.9967 0.9712 0.6502 0.046 Uiso calc U . R 1.0 . .
C C21 0.72446(13) 1.2835(4) 0.49128(9) 0.0236(5) Uani d . . . 1.0 . .
C C22 0.69818(13) 1.4897(4) 0.45588(9) 0.0264(5) Uani d . . . 1.0 . .
H H22 0.7179 1.52 0.4241 0.032 Uiso calc U . R 1.0 . .
C C23 0.64410(13) 1.6504(4) 0.46620(10) 0.0287(5) Uani d . . . 1.0 . .
H H23 0.6264 1.7888 0.4413 0.034 Uiso calc U . R 1.0 . .
C C24 0.61534(13) 1.6108(4) 0.51294(10) 0.0259(5) Uani d . . . 1.0 . .
C C25 0.53915(15) 1.7712(5) 0.57076(10) 0.0346(6) Uani d . . . 1.0 . .
H H25A 0.5116 1.6153 0.5721 0.052 Uiso calc U . R 1.0 . .
H H25B 0.5043 1.9108 0.5711 0.052 Uiso calc U . R 1.0 . .
H H25C 0.5861 1.7818 0.6049 0.052 Uiso calc U . R 1.0 . .
C C26 0.64080(14) 1.4078(4) 0.54882(10) 0.0288(5) Uani d . . . 1.0 . .
H H26 0.6215 1.3794 0.5809 0.035 Uiso calc U . R 1.0 . .
C C27 0.69441(14) 1.2469(4) 0.53760(10) 0.0293(5) Uani d . . . 1.0 . .
H H27 0.7113 1.107 0.5622 0.035 Uiso calc U . R 1.0 . .
F F1 0.8532(9) 1.0073(16) 0.7875(6) 0.065(3) Uani d U P D 0.54(4) A 1
F F2 0.8196(8) 0.628(3) 0.7909(6) 0.077(3) Uani d U P D 0.54(4) A 1
F F3 0.9388(5) 0.739(3) 0.8289(4) 0.055(2) Uani d U P D 0.54(4) A 1
F F1A 0.9423(6) 0.800(4) 0.8256(6) 0.070(4) Uani d U P D 0.46(4) A 2
F F2A 0.8286(11) 0.950(3) 0.7823(8) 0.083(3) Uani d U P D 0.46(4) A 2
F F3A 0.8429(12) 0.560(3) 0.7957(6) 0.078(3) Uani d U P D 0.46(4) A 2
N N1 0.89035(11) 0.7807(4) 0.45876(9) 0.0320(5) Uani d . . . 1.0 . .
O O1 0.87225(8) 0.8134(3) 0.18784(6) 0.0268(4) Uani d . . . 1.0 . .
O O2 0.56161(9) 1.7794(3) 0.51875(7) 0.0329(4) Uani d . . . 1.0 . .


_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 O1 . 1.431(3) ?
C2 O1 . 1.372(2) ?
C2 C3 . 1.383(3) ?
C2 C7 . 1.395(3) ?
C3 C4 . 1.388(3) ?
C4 C5 . 1.392(3) ?
C5 C6 . 1.396(3) ?
C5 C8 . 1.489(3) ?
C6 C7 . 1.376(3) ?
C8 N1 . 1.362(3) ?
C8 C9 . 1.392(3) ?
C9 C10 . 1.386(3) ?
C10 C11 . 1.373(3) ?
C10 C21 . 1.482(3) ?
C11 C12 . 1.364(3) ?
C12 N1 . 1.366(3) ?
C12 C13 . 1.512(3) ?
C13 C14 . 1.508(3) ?
C14 C20 . 1.380(4) ?
C14 C15 . 1.383(4) ?
C15 C16 . 1.380(4) ?
C16 C17 . 1.376(4) ?
C17 C19 . 1.374(4) ?
C17 C18 . 1.479(4) ?
C18 F2A . 1.308(9) ?
C18 F1A . 1.334(9) ?
C18 F2 . 1.335(7) ?
C18 F3 . 1.336(8) ?
C18 F3A . 1.359(8) ?
C18 F1 . 1.380(7) ?
C19 C20 . 1.379(4) ?
C21 C27 . 1.392(3) ?
C21 C22 . 1.393(3) ?
C22 C23 . 1.377(3) ?
C23 C24 . 1.389(3) ?
C24 O2 . 1.362(3) ?
C24 C26 . 1.383(3) ?
C25 O2 . 1.428(3) ?
C26 C27 . 1.381(3) ?

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
O1 C2 C3 . . 124.96(19) ?
O1 C2 C7 . . 115.20(19) ?
C3 C2 C7 . . 119.84(19) ?
C2 C3 C4 . . 119.4(2) ?
C3 C4 C5 . . 122.0(2) ?
C4 C5 C6 . . 117.29(19) ?
C4 C5 C8 . . 121.43(19) ?
C6 C5 C8 . . 121.28(19) ?
C7 C6 C5 . . 121.7(2) ?
C6 C7 C2 . . 119.8(2) ?
N1 C8 C9 . . 120.58(19) ?
N1 C8 C5 . . 118.21(19) ?
C9 C8 C5 . . 121.20(19) ?
C10 C9 C8 . . 120.3(2) ?
C11 C10 C9 . . 118.7(2) ?
C11 C10 C21 . . 120.34(19) ?
C9 C10 C21 . . 121.0(2) ?
C12 C11 C10 . . 119.5(2) ?
C11 C12 N1 . . 123.0(2) ?
C11 C12 C13 . . 121.2(2) ?
N1 C12 C13 . . 115.8(2) ?
C14 C13 C12 . . 114.6(2) ?
C20 C14 C15 . . 117.9(2) ?
C20 C14 C13 . . 121.3(2) ?
C15 C14 C13 . . 120.8(3) ?
C16 C15 C14 . . 121.1(3) ?
C17 C16 C15 . . 120.2(3) ?
C19 C17 C16 . . 119.2(2) ?
C19 C17 C18 . . 118.7(3) ?
C16 C17 C18 . . 122.1(3) ?
F2A C18 F1A . . 108.2(9) ?
F2 C18 F3 . . 105.9(7) ?
F2A C18 F3A . . 106.3(7) ?
F1A C18 F3A . . 105.3(8) ?
F2 C18 F1 . . 104.2(6) ?
F3 C18 F1 . . 102.8(6) ?
F2A C18 C17 . . 114.6(8) ?
F1A C18 C17 . . 111.8(8) ?
F2 C18 C17 . . 116.6(6) ?
F3 C18 C17 . . 114.8(5) ?
F3A C18 C17 . . 110.0(8) ?
F1 C18 C17 . . 111.2(6) ?
C17 C19 C20 . . 120.3(2) ?
C19 C20 C14 . . 121.1(2) ?
C27 C21 C22 . . 117.6(2) ?
C27 C21 C10 . . 121.4(2) ?
C22 C21 C10 . . 121.1(2) ?
C23 C22 C21 . . 121.1(2) ?
C22 C23 C24 . . 120.2(2) ?
O2 C24 C26 . . 125.0(2) ?
O2 C24 C23 . . 115.3(2) ?
C26 C24 C23 . . 119.7(2) ?
C27 C26 C24 . . 119.5(2) ?
C26 C27 C21 . . 121.9(2) ?
C8 N1 C12 . . 117.93(19) ?
C2 O1 C1 . . 117.51(18) ?
C24 O2 C25 . . 117.78(18) ?



####################################################################### 
# 
# 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 1051372'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H57 Au Cl3 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         891.21

_chemical_melting_point          ?

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

_cell_length_a                   20.7969(9)
_cell_length_b                   9.1006(3)
_cell_length_c                   22.4423(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.9810(10)
_cell_angle_gamma                90
_cell_volume                     4103.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8784
_cell_measurement_theta_min      2.7226
_cell_measurement_theta_max      28.2738
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808

_exptl_absorpt_coefficient_mu    3.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.86

_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  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            37965
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27

_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.
;
_reflns_number_total             10122
_reflns_number_gt                8356
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1129
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.162
_refine_ls_number_reflns         10122
_refine_ls_number_parameters     467
_refine_ls_number_restraints     47
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0591P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.564
_refine_diff_density_min         -1.541
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker Apex2'
_computing_publication_material  'Bruker Apex2'

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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au Au1 0.309249(7) 0.514654(17) 0.41827(8) 0.01288(7) Uani d . 1.0 . .
C C1 0.28450(19) 0.6538(4) 0.4770(2) 0.0107(8) Uani d . 1.0 . .
C C2 0.32100(19) 0.8448(4) 0.5534(2) 0.0125(8) Uani d . 1.0 . .
H H2 0.3562 0.9071 0.5744 0.015 Uiso calc R 1.0 . .
C C3 0.26067(19) 0.8502(4) 0.5681(2) 0.0112(8) Uani d . 1.0 . .
C C4 0.21130(18) 0.7558(4) 0.53520(19) 0.0099(8) Uani d . 1.0 . .
H H4 0.1688 0.7578 0.5437 0.012 Uiso calc R 1.0 . .
C C5 0.22144(19) 0.6595(4) 0.49081(19) 0.0096(8) Uani d . 1.0 . .
C C6 0.39670(19) 0.7591(5) 0.4966(2) 0.0138(9) Uani d . 1.0 . .
C C7 0.4491(2) 0.6843(5) 0.5363(2) 0.0155(9) Uani d . 1.0 . .
C C8 0.4398(2) 0.5938(6) 0.5900(2) 0.0262(11) Uani d . 1.0 . .
H H8A 0.4318 0.6592 0.622 0.039 Uiso calc R 1.0 . .
H H8B 0.48 0.5356 0.607 0.039 Uiso calc R 1.0 . .
H H8C 0.4017 0.5278 0.5758 0.039 Uiso calc R 1.0 . .
C C9 0.5112(2) 0.6977(5) 0.5245(2) 0.0185(10) Uani d . 1.0 . .
H H9 0.5481 0.6478 0.5504 0.022 Uiso calc R 1.0 . .
C C10 0.5210(2) 0.7811(5) 0.4764(2) 0.0181(10) Uani d . 1.0 . .
C C11 0.5897(2) 0.7968(6) 0.4662(3) 0.0253(11) Uani d . 1.0 . .
H H11A 0.6089 0.8912 0.4829 0.038 Uiso calc R 1.0 . .
H H11B 0.5866 0.7928 0.4219 0.038 Uiso calc R 1.0 . .
H H11C 0.6181 0.7166 0.4872 0.038 Uiso calc R 1.0 . .
C C12 0.4675(2) 0.8526(5) 0.4382(2) 0.0198(10) Uani d . 1.0 . .
H H12 0.4744 0.9093 0.4049 0.024 Uiso calc R 1.0 . .
C C13 0.4035(2) 0.8442(5) 0.4470(2) 0.0156(9) Uani d . 1.0 . .
C C14 0.3461(2) 0.9217(5) 0.4036(2) 0.0225(10) Uani d . 1.0 . .
H H14A 0.3187 0.8498 0.3757 0.034 Uiso calc R 1.0 . .
H H14B 0.3633 0.9946 0.3795 0.034 Uiso calc R 1.0 . .
H H14C 0.3191 0.9711 0.4274 0.034 Uiso calc R 1.0 . .
C C15 0.24932(19) 0.9491(5) 0.6166(2) 0.0120(8) Uani d . 1.0 . .
C C16 0.27490(19) 1.0914(4) 0.6246(2) 0.0119(8) Uani d . 1.0 . .
H H16 0.3014 1.1258 0.5988 0.014 Uiso calc R 1.0 . .
C C17 0.26236(19) 1.1840(4) 0.6697(2) 0.0114(8) Uani d . 1.0 . .
C C18 0.29232(19) 1.3389(4) 0.6783(2) 0.0123(8) Uani d . 1.0 . .
C C19 0.2776(2) 1.4180(5) 0.6163(2) 0.0183(9) Uani d . 1.0 . .
H H19A 0.3001 1.3671 0.5889 0.027 Uiso calc R 1.0 . .
H H19B 0.2938 1.5194 0.6225 0.027 Uiso calc R 1.0 . .
H H19C 0.2295 1.4183 0.5976 0.027 Uiso calc R 1.0 . .
C C20 0.3681(2) 1.3275(5) 0.7053(2) 0.0177(9) Uani d . 1.0 . .
H H20A 0.3874 1.2683 0.6778 0.027 Uiso calc R 1.0 . .
H H20B 0.3774 1.2807 0.746 0.027 Uiso calc R 1.0 . .
H H20C 0.3876 1.4261 0.7094 0.027 Uiso calc R 1.0 . .
C C21 0.2636(2) 1.4320(5) 0.7225(2) 0.0189(10) Uani d . 1.0 . .
H H21A 0.2838 1.53 0.7266 0.028 Uiso calc R 1.0 . .
H H21B 0.2735 1.3844 0.7631 0.028 Uiso calc R 1.0 . .
H H21C 0.2153 1.4407 0.7061 0.028 Uiso calc R 1.0 . .
C C22 0.22328(19) 1.1302(4) 0.70661(19) 0.0112(8) Uani d . 1.0 . .
H H22 0.2138 1.1928 0.7371 0.013 Uiso calc R 1.0 . .
C C23 0.1975(2) 0.9874(4) 0.7004(2) 0.0132(9) Uani d . 1.0 . .
C C24 0.1559(2) 0.9256(5) 0.7425(2) 0.0150(9) Uani d . 1.0 . .
C C25 0.1933(2) 0.7975(5) 0.7801(2) 0.0255(11) Uani d . 1.0 . .
H H25A 0.1666 0.7568 0.8063 0.038 Uiso calc R 1.0 . .
H H25B 0.2359 0.8325 0.806 0.038 Uiso calc R 1.0 . .
H H25C 0.2013 0.7211 0.7521 0.038 Uiso calc R 1.0 . .
C C26 0.0892(2) 0.8688(6) 0.7023(2) 0.0265(11) Uani d . 1.0 . .
H H26A 0.0974 0.7919 0.6746 0.04 Uiso calc R 1.0 . .
H H26B 0.0648 0.95 0.6778 0.04 Uiso calc R 1.0 . .
H H26C 0.0627 0.8284 0.7287 0.04 Uiso calc R 1.0 . .
C C27 0.1406(2) 1.0432(5) 0.7859(2) 0.0210(10) Uani d . 1.0 . .
H H27A 0.1148 1.1229 0.7615 0.031 Uiso calc R 1.0 . .
H H27B 0.1824 1.0827 0.8118 0.031 Uiso calc R 1.0 . .
H H27C 0.1148 0.9993 0.8122 0.031 Uiso calc R 1.0 . .
C C28 0.21109(18) 0.8984(4) 0.6550(2) 0.0124(9) Uani d . 1.0 . .
H H28 0.194 0.8011 0.6499 0.015 Uiso calc R 1.0 . .
C C29 0.16541(18) 0.5616(5) 0.45912(19) 0.0097(8) Uani d . 1.0 . .
C C30 0.10174(19) 0.6202(5) 0.43600(19) 0.0115(8) Uani d . 1.0 . .
H H30 0.0952 0.7231 0.4386 0.014 Uiso calc R 1.0 . .
C C31 0.0473(2) 0.5305(4) 0.4091(2) 0.0115(8) Uani d . 1.0 . .
C C32 -0.02315(19) 0.5923(5) 0.3834(2) 0.0151(9) Uani d . 1.0 . .
C C33 -0.0451(2) 0.5648(6) 0.3130(2) 0.0220(10) Uani d . 1.0 . .
H H33A -0.0422 0.4596 0.3049 0.033 Uiso calc R 1.0 . .
H H33B -0.0159 0.6194 0.2929 0.033 Uiso calc R 1.0 . .
H H33C -0.0912 0.5979 0.2967 0.033 Uiso calc R 1.0 . .
C C34 -0.0265(2) 0.7574(5) 0.3944(3) 0.0259(12) Uani d . 1.0 . .
H H34A -0.0721 0.7922 0.3769 0.039 Uiso calc R 1.0 . .
H H34B 0.0038 0.8087 0.3745 0.039 Uiso calc R 1.0 . .
H H34C -0.0134 0.7772 0.4388 0.039 Uiso calc R 1.0 . .
C C35 -0.0711(2) 0.5141(5) 0.4141(3) 0.0221(11) Uani d . 1.0 . .
H H35A -0.0567 0.5294 0.4588 0.033 Uiso calc R 1.0 . .
H H35B -0.0713 0.4087 0.4051 0.033 Uiso calc R 1.0 . .
H H35C -0.116 0.554 0.398 0.033 Uiso calc R 1.0 . .
C C36 0.0594(2) 0.3793(5) 0.4062(2) 0.0132(9) Uani d . 1.0 . .
H H36 0.0231 0.3163 0.3885 0.016 Uiso calc R 1.0 . .
C C37 0.12216(19) 0.3178(4) 0.4282(2) 0.0115(8) Uani d . 1.0 . .
C C38 0.1315(2) 0.1522(5) 0.4251(2) 0.0157(9) Uani d . 1.0 . .
C C39 0.1028(3) 0.0972(5) 0.3584(2) 0.0275(12) Uani d . 1.0 . .
H H39A 0.1289 0.1381 0.3317 0.041 Uiso calc R 1.0 . .
H H39B 0.0564 0.1291 0.3436 0.041 Uiso calc R 1.0 . .
H H39C 0.1049 -0.0103 0.3576 0.041 Uiso calc R 1.0 . .
C C40 0.0953(3) 0.0789(5) 0.4688(3) 0.0267(12) Uani d . 1.0 . .
H H40A 0.1012 -0.0279 0.4679 0.04 Uiso calc R 1.0 . .
H H40B 0.0478 0.1026 0.4556 0.04 Uiso calc R 1.0 . .
H H40C 0.1139 0.1151 0.5109 0.04 Uiso calc R 1.0 . .
C C41 0.2045(2) 0.1093(5) 0.4452(2) 0.0215(10) Uani d . 1.0 . .
H H41A 0.2292 0.163 0.4203 0.032 Uiso calc R 1.0 . .
H H41B 0.2089 0.0034 0.4393 0.032 Uiso calc R 1.0 . .
H H41C 0.2225 0.1339 0.4888 0.032 Uiso calc R 1.0 . .
C C42 0.17515(19) 0.4102(5) 0.45452(19) 0.0117(8) Uani d . 1.0 . .
H H42 0.2185 0.3701 0.4696 0.014 Uiso calc R 1.0 . .
Cl Cl1 0.33603(6) 0.34778(13) 0.35254(6) 0.0256(3) Uani d . 1.0 . .
Cl Cl2 0.45440(8) 0.5433(2) 0.19841(10) 0.0548(5) Uani d D 1.0 . .
C C43 0.4058(6) 0.5693(13) 0.2520(6) 0.043(2) Uani d PDU 0.788(14) A 1
H H43A 0.363 0.5161 0.2376 0.052 Uiso calc PR 0.788(14) A 1
H H43B 0.4296 0.5285 0.2926 0.052 Uiso calc PR 0.788(14) A 1
Cl Cl3 0.3904(3) 0.7541(3) 0.2597(3) 0.0770(16) Uani d PDU 0.788(14) A 1
C C43A 0.395(2) 0.560(5) 0.244(2) 0.039(5) Uani d PDU 0.212(14) A 2
H H43C 0.3499 0.5713 0.217 0.047 Uiso calc PR 0.212(14) A 2
H H43D 0.3966 0.4708 0.2697 0.047 Uiso calc PR 0.212(14) A 2
Cl Cl3A 0.4189(10) 0.718(2) 0.2913(10) 0.088(4) Uani d PDU 0.212(14) A 2
N N1 0.33075(16) 0.7517(4) 0.50941(17) 0.0117(7) Uani d . 1.0 . .


_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
Au1 C1 . 1.989(4) ?
Au1 Cl1 . 2.2842(11) ?
C1 N1 . 1.373(5) ?
C1 C5 . 1.424(5) ?
C2 N1 . 1.355(5) ?
C2 C3 . 1.378(5) ?
C2 H2 . 0.95 ?
C3 C4 . 1.394(5) ?
C3 C15 . 1.478(6) ?
C4 C5 . 1.383(6) ?
C4 H4 . 0.95 ?
C5 C29 . 1.493(5) ?
C6 C13 . 1.393(6) ?
C6 C7 . 1.393(6) ?
C6 N1 . 1.474(5) ?
C7 C9 . 1.390(6) ?
C7 C8 . 1.513(7) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 C10 . 1.377(7) ?
C9 H9 . 0.95 ?
C10 C12 . 1.379(6) ?
C10 C11 . 1.510(6) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C13 . 1.396(6) ?
C12 H12 . 0.95 ?
C13 C14 . 1.507(6) ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 C28 . 1.393(6) ?
C15 C16 . 1.394(6) ?
C16 C17 . 1.393(6) ?
C16 H16 . 0.95 ?
C17 C22 . 1.391(6) ?
C17 C18 . 1.533(5) ?
C18 C19 . 1.525(6) ?
C18 C21 . 1.538(6) ?
C18 C20 . 1.538(5) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 C23 . 1.399(5) ?
C22 H22 . 0.95 ?
C23 C28 . 1.388(6) ?
C23 C24 . 1.542(6) ?
C24 C25 . 1.528(6) ?
C24 C26 . 1.536(6) ?
C24 C27 . 1.536(6) ?
C25 H25A . 0.98 ?
C25 H25B . 0.98 ?
C25 H25C . 0.98 ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28 . 0.95 ?
C29 C30 . 1.397(5) ?
C29 C42 . 1.401(6) ?
C30 C31 . 1.399(5) ?
C30 H30 . 0.95 ?
C31 C36 . 1.403(6) ?
C31 C32 . 1.536(5) ?
C32 C35 . 1.526(6) ?
C32 C34 . 1.527(6) ?
C32 C33 . 1.547(6) ?
C33 H33A . 0.98 ?
C33 H33B . 0.98 ?
C33 H33C . 0.98 ?
C34 H34A . 0.98 ?
C34 H34B . 0.98 ?
C34 H34C . 0.98 ?
C35 H35A . 0.98 ?
C35 H35B . 0.98 ?
C35 H35C . 0.98 ?
C36 C37 . 1.388(5) ?
C36 H36 . 0.95 ?
C37 C42 . 1.391(5) ?
C37 C38 . 1.523(6) ?
C38 C41 . 1.518(6) ?
C38 C40 . 1.536(6) ?
C38 C39 . 1.544(7) ?
C39 H39A . 0.98 ?
C39 H39B . 0.98 ?
C39 H39C . 0.98 ?
C40 H40A . 0.98 ?
C40 H40B . 0.98 ?
C40 H40C . 0.98 ?
C41 H41A . 0.98 ?
C41 H41B . 0.98 ?
C41 H41C . 0.98 ?
C42 H42 . 0.95 ?
Cl2 C43 . 1.776(9) ?
Cl2 C43A . 1.793(19) ?
C43 Cl3 . 1.729(12) ?
C43 H43A . 0.99 ?
C43 H43B . 0.99 ?
C43A Cl3A . 1.78(2) ?
C43A H43C . 0.99 ?
C43A H43D . 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
C1 Au1 Cl1 . . 177.84(12) ?
N1 C1 C5 . . 114.8(4) ?
N1 C1 Au1 . . 119.9(3) ?
C5 C1 Au1 . . 125.3(3) ?
N1 C2 C3 . . 120.9(4) ?
N1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C2 C3 C4 . . 116.3(4) ?
C2 C3 C15 . . 121.8(4) ?
C4 C3 C15 . . 121.9(4) ?
C5 C4 C3 . . 122.9(4) ?
C5 C4 H4 . . 118.6 ?
C3 C4 H4 . . 118.6 ?
C4 C5 C1 . . 120.0(4) ?
C4 C5 C29 . . 118.4(4) ?
C1 C5 C29 . . 121.6(4) ?
C13 C6 C7 . . 123.9(4) ?
C13 C6 N1 . . 118.3(4) ?
C7 C6 N1 . . 117.8(4) ?
C9 C7 C6 . . 116.6(4) ?
C9 C7 C8 . . 121.0(4) ?
C6 C7 C8 . . 122.4(4) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C7 . . 122.1(4) ?
C10 C9 H9 . . 119.0 ?
C7 C9 H9 . . 119.0 ?
C9 C10 C12 . . 119.2(4) ?
C9 C10 C11 . . 120.5(4) ?
C12 C10 C11 . . 120.3(4) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 C13 . . 122.1(4) ?
C10 C12 H12 . . 118.9 ?
C13 C12 H12 . . 118.9 ?
C6 C13 C12 . . 116.2(4) ?
C6 C13 C14 . . 123.3(4) ?
C12 C13 C14 . . 120.5(4) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C28 C15 C16 . . 119.2(4) ?
C28 C15 C3 . . 118.6(4) ?
C16 C15 C3 . . 122.1(4) ?
C17 C16 C15 . . 121.2(4) ?
C17 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
C22 C17 C16 . . 117.9(4) ?
C22 C17 C18 . . 122.0(4) ?
C16 C17 C18 . . 120.1(4) ?
C19 C18 C17 . . 109.9(3) ?
C19 C18 C21 . . 108.0(4) ?
C17 C18 C21 . . 112.0(3) ?
C19 C18 C20 . . 109.6(4) ?
C17 C18 C20 . . 109.2(3) ?
C21 C18 C20 . . 108.1(4) ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C18 C20 H20A . . 109.5 ?
C18 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C18 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C17 C22 C23 . . 122.4(4) ?
C17 C22 H22 . . 118.8 ?
C23 C22 H22 . . 118.8 ?
C28 C23 C22 . . 117.9(4) ?
C28 C23 C24 . . 119.4(4) ?
C22 C23 C24 . . 122.7(4) ?
C25 C24 C26 . . 108.8(4) ?
C25 C24 C27 . . 109.9(4) ?
C26 C24 C27 . . 107.7(4) ?
C25 C24 C23 . . 109.3(4) ?
C26 C24 C23 . . 109.1(4) ?
C27 C24 C23 . . 112.0(4) ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C24 C26 H26A . . 109.5 ?
C24 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C24 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C24 C27 H27A . . 109.5 ?
C24 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C24 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C23 C28 C15 . . 121.3(4) ?
C23 C28 H28 . . 119.4 ?
C15 C28 H28 . . 119.4 ?
C30 C29 C42 . . 119.3(4) ?
C30 C29 C5 . . 119.8(4) ?
C42 C29 C5 . . 120.8(3) ?
C29 C30 C31 . . 121.4(4) ?
C29 C30 H30 . . 119.3 ?
C31 C30 H30 . . 119.3 ?
C30 C31 C36 . . 117.2(4) ?
C30 C31 C32 . . 122.3(4) ?
C36 C31 C32 . . 120.5(4) ?
C35 C32 C34 . . 108.9(4) ?
C35 C32 C31 . . 109.4(4) ?
C34 C32 C31 . . 112.3(3) ?
C35 C32 C33 . . 109.3(4) ?
C34 C32 C33 . . 108.1(4) ?
C31 C32 C33 . . 108.9(4) ?
C32 C33 H33A . . 109.5 ?
C32 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C32 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C32 C34 H34A . . 109.5 ?
C32 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C32 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C32 C35 H35A . . 109.5 ?
C32 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C32 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C37 C36 C31 . . 122.9(4) ?
C37 C36 H36 . . 118.6 ?
C31 C36 H36 . . 118.6 ?
C36 C37 C42 . . 118.4(4) ?
C36 C37 C38 . . 120.2(4) ?
C42 C37 C38 . . 121.4(4) ?
C41 C38 C37 . . 111.7(3) ?
C41 C38 C40 . . 108.4(4) ?
C37 C38 C40 . . 108.1(4) ?
C41 C38 C39 . . 108.1(4) ?
C37 C38 C39 . . 110.0(4) ?
C40 C38 C39 . . 110.4(4) ?
C38 C39 H39A . . 109.5 ?
C38 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C38 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C38 C40 H40A . . 109.5 ?
C38 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
C38 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 109.5 ?
C38 C41 H41A . . 109.5 ?
C38 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C38 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C37 C42 C29 . . 120.8(4) ?
C37 C42 H42 . . 119.6 ?
C29 C42 H42 . . 119.6 ?
C43 Cl2 C43A . . 8.3(17) ?
Cl3 C43 Cl2 . . 110.4(7) ?
Cl3 C43 H43A . . 109.6 ?
Cl2 C43 H43A . . 109.6 ?
Cl3 C43 H43B . . 109.6 ?
Cl2 C43 H43B . . 109.6 ?
H43A C43 H43B . . 108.1 ?
Cl3A C43A Cl2 . . 106.5(13) ?
Cl3A C43A H43C . . 110.4 ?
Cl2 C43A H43C . . 110.4 ?
Cl3A C43A H43D . . 110.4 ?
Cl2 C43A H43D . . 110.4 ?
H43C C43A H43D . . 108.6 ?
C2 N1 C1 . . 125.1(3) ?
C2 N1 C6 . . 115.8(3) ?
C1 N1 C6 . . 119.1(3) ?

