# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_g271
_database_code_depnum_ccdc_archive 'CCDC 1536807'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13.50 H11 B0.50 F N O0.50'
_chemical_formula_sum            'C13.50 H11 B0.50 F N O0.50'
_chemical_formula_weight         219.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.1844(5)
_cell_length_b                   20.7250(6)
_cell_length_c                   6.8775(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.9610(10)
_cell_angle_gamma                90
_cell_volume                     2124.84(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    985
_cell_measurement_theta_min      3.652
_cell_measurement_theta_max      72.278

_exptl_crystal_description       'prism frag'
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.777
_shelx_estimated_absorpt_T_min   0.690
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   Sadabs
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from θ/2θ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9574
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.652
_diffrn_reflns_theta_max         72.278
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2077
_reflns_number_gt                1838
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 v2015.5.2'
_computing_cell_refinement       
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_reduction        'Saint, APEX v2014.11.0.'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2015.5.2'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²+1.5525P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2077
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.5000 0.87969(11) 0.2500 0.0413(7) Uani 1 2 d S T P . .
F1 F 0.56308(7) 0.91836(5) 0.3683(2) 0.0703(5) Uani 1 1 d . . . . .
N1 N 0.45393(8) 0.83555(6) 0.3817(2) 0.0337(3) Uani 1 1 d . . . . .
O1 O 0.5000 0.46437(7) 0.2500 0.0409(4) Uani 1 2 d S T P . .
C1 C 0.40736(12) 0.85413(8) 0.5208(3) 0.0440(4) Uani 1 1 d . . . . .
C2 C 0.37835(12) 0.79963(8) 0.6113(3) 0.0451(4) Uani 1 1 d . . . . .
H2 H 0.3442 0.8000 0.7135 0.054 Uiso 1 1 calc R U . . .
C3 C 0.40783(10) 0.74525(7) 0.5267(2) 0.0332(4) Uani 1 1 d . . . . .
C4 C 0.45562(9) 0.76788(6) 0.3807(2) 0.0268(3) Uani 1 1 d . . . . .
C5 C 0.5000 0.73521(8) 0.2500 0.0229(4) Uani 1 2 d S T P . .
C6 C 0.5000 0.66343(8) 0.2500 0.0220(4) Uani 1 2 d S T P . .
C7 C 0.57921(8) 0.62963(6) 0.33899(19) 0.0230(3) Uani 1 1 d . . . . .
C8 C 0.65883(9) 0.66259(7) 0.4276(2) 0.0259(3) Uani 1 1 d . . . . .
H8 H 0.6596 0.7084 0.4294 0.031 Uiso 1 1 calc R U . . .
C9 C 0.73474(9) 0.62896(7) 0.5108(2) 0.0307(3) Uani 1 1 d . . . . .
H9 H 0.7875 0.6517 0.5691 0.037 Uiso 1 1 calc R U . . .
C10 C 0.73468(10) 0.56167(7) 0.5100(2) 0.0339(4) Uani 1 1 d . . . . .
H10 H 0.7874 0.5388 0.5678 0.041 Uiso 1 1 calc R U . . .
C11 C 0.65863(10) 0.52816(7) 0.4258(2) 0.0327(4) Uani 1 1 d . . . . .
H11 H 0.6593 0.4823 0.4262 0.039 Uiso 1 1 calc R U . . .
C12 C 0.58036(9) 0.56105(6) 0.3396(2) 0.0262(3) Uani 1 1 d . . . . .
C13 C 0.38962(16) 0.92314(9) 0.5612(4) 0.0653(7) Uani 1 1 d . . . . .
H13A H 0.4442 0.9485 0.5623 0.098 Uiso 1 1 calc R U . . .
H13B H 0.3716 0.9267 0.6902 0.098 Uiso 1 1 calc R U . . .
H13C H 0.3414 0.9395 0.4576 0.098 Uiso 1 1 calc R U . . .
C14 C 0.39007(12) 0.67728(8) 0.5815(2) 0.0403(4) Uani 1 1 d . . . . .
H14A H 0.3720 0.6768 0.7110 0.060 Uiso 1 1 calc R U . . .
H14B H 0.4447 0.6515 0.5880 0.060 Uiso 1 1 calc R U . . .
H14C H 0.3419 0.6590 0.4815 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5000 0.52423(9) 0.2500 0.0297(4) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.3875(16) . ?
B1 F1 1.3876(16) 2_655 ?
B1 N1 1.5450(19) 2_655 ?
B1 N1 1.5450(19) . ?
N1 C1 1.349(2) . ?
N1 C4 1.4028(17) . ?
O1 C15 1.241(2) . ?
C1 C2 1.400(3) . ?
C1 C13 1.491(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.425(2) . ?
C3 C14 1.496(2) . ?
C4 C5 1.3968(16) . ?
C5 C4 1.3968(16) 2_655 ?
C5 C6 1.488(2) . ?
C6 C7 1.4255(15) . ?
C6 C7 1.4255(15) 2_655 ?
C7 C8 1.4212(18) . ?
C7 C12 1.4213(18) . ?
C8 C9 1.3751(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.4003(19) . ?
C11 H11 0.9500 . ?
C12 C15 1.4714(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C12 1.4714(17) 2_655 ?

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
F1 B1 F1 109.42(19) . 2_655 ?
F1 B1 N1 110.28(6) . 2_655 ?
F1 B1 N1 109.72(8) 2_655 2_655 ?
F1 B1 N1 109.72(8) . . ?
F1 B1 N1 110.28(6) 2_655 . ?
N1 B1 N1 107.40(16) 2_655 . ?
C1 N1 C4 107.52(13) . . ?
C1 N1 B1 127.12(13) . . ?
C4 N1 B1 125.34(12) . . ?
N1 C1 C2 109.66(13) . . ?
N1 C1 C13 122.90(19) . . ?
C2 C1 C13 127.42(18) . . ?
C3 C2 C1 108.46(16) . . ?
C3 C2 H2 125.8 . . ?
C1 C2 H2 125.8 . . ?
C2 C3 C4 106.10(14) . . ?
C2 C3 C14 125.03(15) . . ?
C4 C3 C14 128.87(13) . . ?
C5 C4 N1 119.95(13) . . ?
C5 C4 C3 131.79(13) . . ?
N1 C4 C3 108.26(12) . . ?
C4 C5 C4 122.02(17) . 2_655 ?
C4 C5 C6 118.99(9) . . ?
C4 C5 C6 118.99(9) 2_655 . ?
C7 C6 C7 121.13(16) . 2_655 ?
C7 C6 C5 119.44(8) . . ?
C7 C6 C5 119.44(8) 2_655 . ?
C8 C7 C12 118.07(12) . . ?
C8 C7 C6 121.83(12) . . ?
C12 C7 C6 120.10(12) . . ?
C9 C8 C7 120.81(12) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.35(13) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.39(13) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.59(13) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.80(12) . . ?
C11 C12 C15 119.63(13) . . ?
C7 C12 C15 120.58(12) . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C12 121.24(8) . . ?
O1 C15 C12 121.24(8) . 2_655 ?
C12 C15 C12 117.51(16) . 2_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 B1 N1 C1 58.90(17) . . . . ?
F1 B1 N1 C1 -61.70(18) 2_655 . . . ?
N1 B1 N1 C1 178.77(15) 2_655 . . . ?
F1 B1 N1 C4 -119.14(15) . . . . ?
F1 B1 N1 C4 120.26(16) 2_655 . . . ?
N1 B1 N1 C4 0.74(9) 2_655 . . . ?
C4 N1 C1 C2 -0.04(17) . . . . ?
B1 N1 C1 C2 -178.36(12) . . . . ?
C4 N1 C1 C13 -178.52(15) . . . . ?
B1 N1 C1 C13 3.2(2) . . . . ?
N1 C1 C2 C3 0.17(19) . . . . ?
C13 C1 C2 C3 178.56(17) . . . . ?
C1 C2 C3 C4 -0.23(18) . . . . ?
C1 C2 C3 C14 -179.50(15) . . . . ?
C1 N1 C4 C5 -179.83(11) . . . . ?
B1 N1 C4 C5 -1.47(17) . . . . ?
C1 N1 C4 C3 -0.10(16) . . . . ?
B1 N1 C4 C3 178.26(10) . . . . ?
C2 C3 C4 C5 179.89(13) . . . . ?
C14 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 N1 0.20(16) . . . . ?
C14 C3 C4 N1 179.44(15) . . . . ?
N1 C4 C5 C4 0.71(8) . . . 2_655 ?
C3 C4 C5 C4 -178.95(17) . . . 2_655 ?
N1 C4 C5 C6 -179.29(8) . . . . ?
C3 C4 C5 C6 1.05(17) . . . . ?
C4 C5 C6 C7 -104.80(8) . . . . ?
C4 C5 C6 C7 75.20(8) 2_655 . . . ?
C4 C5 C6 C7 75.20(8) . . . 2_655 ?
C4 C5 C6 C7 -104.80(8) 2_655 . . 2_655 ?
C7 C6 C7 C8 179.75(13) 2_655 . . . ?
C5 C6 C7 C8 -0.25(13) . . . . ?
C7 C6 C7 C12 0.22(8) 2_655 . . . ?
C5 C6 C7 C12 -179.78(8) . . . . ?
C12 C7 C8 C9 0.21(19) . . . . ?
C6 C7 C8 C9 -179.32(11) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C10 C11 C12 C15 179.83(12) . . . . ?
C8 C7 C12 C11 -0.08(19) . . . . ?
C6 C7 C12 C11 179.46(11) . . . . ?
C8 C7 C12 C15 -179.98(10) . . . . ?
C6 C7 C12 C15 -0.43(16) . . . . ?
C11 C12 C15 O1 0.32(14) . . . . ?
C7 C12 C15 O1 -179.78(8) . . . . ?
C11 C12 C15 C12 -179.68(14) . . . 2_655 ?
C7 C12 C15 C12 0.22(8) . . . 2_655 ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_g153
_database_code_depnum_ccdc_archive 'CCDC 1536808'
_audit_update_record             
;
2017-03-09 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31.25 H29.50 B Cl0.50 F2 N2 O4'
_chemical_formula_weight         563.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3338(9)
_cell_length_b                   12.5679(14)
_cell_length_c                   14.0639(16)
_cell_angle_alpha                87.509(5)
_cell_angle_beta                 81.274(5)
_cell_angle_gamma                75.494(5)
_cell_volume                     1409.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8059
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      68.28

_exptl_crystal_description       Block
_exptl_crystal_colour            Dark_Red
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             589
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.196
_exptl_absorpt_coefficient_mu    1.213
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6047
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15402
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.179
_diffrn_reflns_theta_max         66.584
_diffrn_reflns_theta_full        66.584
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4923
_reflns_number_gt                4109
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1324P)²+2.1110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4923
_refine_ls_number_parameters     427
_refine_ls_number_restraints     210
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.2449
_refine_ls_wR_factor_gt          0.2314
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7695(4) 0.0672(3) 0.3586(3) 0.0280(8) Uani 1 1 d . . . . .
F1 F 0.7443(3) -0.03808(15) 0.36086(15) 0.0400(5) Uani 1 1 d . . . . .
F2 F 0.9276(2) 0.06258(18) 0.38206(15) 0.0426(5) Uani 1 1 d . . . . .
N1 N 0.7535(3) 0.1189(2) 0.25848(19) 0.0265(6) Uani 1 1 d . . . . .
N2 N 0.6341(3) 0.1414(2) 0.43097(19) 0.0245(6) Uani 1 1 d . . . . .
O1 O 0.3178(5) 0.6016(3) 0.0518(2) 0.0650(9) Uani 1 1 d . . . . .
O2 O 0.3233(3) 0.43874(18) 0.37224(16) 0.0344(6) Uani 1 1 d . . . . .
O3 O 0.2121(3) 0.5406(2) 0.34355(18) 0.0464(7) Uani 1 1 d D . . . .
C1 C 0.8466(4) 0.0791(3) 0.1740(2) 0.0313(7) Uani 1 1 d . . . . .
C2 C 0.7994(4) 0.1531(3) 0.0996(2) 0.0351(8) Uani 1 1 d . . . . .
H2 H 0.8449 0.1446 0.0334 0.042 Uiso 1 1 calc R U . . .
C3 C 0.6751(4) 0.2403(3) 0.1400(2) 0.0315(7) Uani 1 1 d . . . . .
H3 H 0.6194 0.3028 0.1068 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6459(4) 0.2196(2) 0.2398(2) 0.0266(7) Uani 1 1 d . . . . .
C5 C 0.5367(4) 0.2819(2) 0.3150(2) 0.0248(6) Uani 1 1 d . . . . .
C6 C 0.5304(4) 0.2443(2) 0.4099(2) 0.0242(6) Uani 1 1 d . . . . .
C7 C 0.4363(4) 0.2873(3) 0.4988(2) 0.0269(7) Uani 1 1 d . . . . .
H7 H 0.3562 0.3561 0.5075 0.032 Uiso 1 1 calc R U . . .
C8 C 0.4811(4) 0.2123(3) 0.5700(2) 0.0301(7) Uani 1 1 d . . . . .
H8 H 0.4377 0.2196 0.6365 0.036 Uiso 1 1 calc R U . . .
C9 C 0.6033(4) 0.1225(2) 0.5261(2) 0.0262(7) Uani 1 1 d . . . . .
C10 C 0.9771(4) -0.0280(3) 0.1660(3) 0.0378(8) Uani 1 1 d . . . . .
H10A H 1.0233 -0.0433 0.2274 0.045 Uiso 1 1 calc R U . . .
H10B H 1.0699 -0.0215 0.1149 0.045 Uiso 1 1 calc R U . . .
C11 C 0.9089(5) -0.1242(3) 0.1430(3) 0.0476(9) Uani 1 1 d . . . . .
H11A H 0.8227 -0.1347 0.1958 0.071 Uiso 1 1 calc R U . . .
H11B H 1.0002 -0.1911 0.1352 0.071 Uiso 1 1 calc R U . . .
H11C H 0.8598 -0.1087 0.0833 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6903(4) 0.0201(3) 0.5731(3) 0.0332(8) Uani 1 1 d . . . . .
H12A H 0.8127 0.0088 0.5543 0.040 Uiso 1 1 calc R U . . .
H12B H 0.6578 -0.0432 0.5489 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6511(5) 0.0216(3) 0.6824(3) 0.0429(9) Uani 1 1 d . . . . .
H13A H 0.6767 0.0864 0.7069 0.064 Uiso 1 1 calc R U . . .
H13B H 0.7191 -0.0451 0.7087 0.064 Uiso 1 1 calc R U . . .
H13C H 0.5320 0.0246 0.7019 0.064 Uiso 1 1 calc R U . . .
C14 C 0.4272(4) 0.3919(3) 0.2847(2) 0.0276(7) Uani 1 1 d . . . . .
C15 C 0.3091(4) 0.3743(3) 0.2174(2) 0.0309(7) Uani 1 1 d . . . . .
C16 C 0.2222(4) 0.2931(3) 0.2392(3) 0.0386(8) Uani 1 1 d . . . . .
H16 H 0.2448 0.2455 0.2925 0.046 Uiso 1 1 calc R U . . .
C17 C 0.1030(5) 0.2806(4) 0.1843(3) 0.0479(10) Uani 1 1 d . . . . .
H17 H 0.0443 0.2249 0.2004 0.057 Uiso 1 1 calc R U . . .
C18 C 0.0696(5) 0.3495(4) 0.1059(3) 0.0487(10) Uani 1 1 d . . . . .
H18 H -0.0104 0.3406 0.0675 0.058 Uiso 1 1 calc R U . . .
C19 C 0.1538(5) 0.4307(3) 0.0846(3) 0.0450(9) Uani 1 1 d . . . . .
H19 H 0.1297 0.4785 0.0316 0.054 Uiso 1 1 calc R U . . .
C20 C 0.2739(4) 0.4444(3) 0.1392(2) 0.0352(8) Uani 1 1 d . . . . .
C21 C 0.3610(5) 0.5338(3) 0.1146(3) 0.0419(9) Uani 1 1 d . . . . .
C22 C 0.5014(5) 0.5375(3) 0.1667(2) 0.0361(8) Uani 1 1 d . . . . .
C23 C 0.5985(6) 0.6119(3) 0.1367(3) 0.0491(10) Uani 1 1 d . . . . .
H23 H 0.5734 0.6596 0.0837 0.059 Uiso 1 1 calc R U . . .
C24 C 0.7296(6) 0.6166(3) 0.1831(3) 0.0539(11) Uani 1 1 d . . . . .
H24 H 0.7967 0.6662 0.1612 0.065 Uiso 1 1 calc R U . . .
C25 C 0.7651(5) 0.5490(3) 0.2625(3) 0.0471(9) Uani 1 1 d . . . . .
H25 H 0.8553 0.5531 0.2950 0.057 Uiso 1 1 calc R U . . .
C26 C 0.6683(4) 0.4758(3) 0.2935(3) 0.0361(8) Uani 1 1 d . . . . .
H26 H 0.6914 0.4302 0.3480 0.043 Uiso 1 1 calc R U . . .
C27 C 0.5372(4) 0.4688(2) 0.2453(2) 0.0300(7) Uani 1 1 d . . . . .
O4 O 0.1965(4) 0.6038(3) 0.4969(2) 0.0422(7) Uani 0.770(4) 1 d D U P A 1
C28 C 0.2383(6) 0.6209(4) 0.3977(3) 0.0401(7) Uani 0.770(4) 1 d D U P A 1
H28 H 0.3565 0.6275 0.3822 0.048 Uiso 0.770(4) 1 calc R U P A 1
C29 C 0.1158(6) 0.7262(4) 0.3697(4) 0.0433(7) Uani 0.770(4) 1 d D U P A 1
H29A H 0.0590 0.7127 0.3161 0.052 Uiso 0.770(4) 1 calc R U P A 1
H29B H 0.1742 0.7851 0.3505 0.052 Uiso 0.770(4) 1 calc R U P A 1
C30 C -0.0117(6) 0.7572(4) 0.4638(4) 0.0462(8) Uani 0.770(4) 1 d D U P A 1
H30A H 0.0079 0.8202 0.4961 0.055 Uiso 0.770(4) 1 calc R U P A 1
H30B H -0.1284 0.7759 0.4499 0.055 Uiso 0.770(4) 1 calc R U P A 1
C31 C 0.0222(6) 0.6573(4) 0.5229(4) 0.0451(7) Uani 0.770(4) 1 d D U P A 1
H31A H -0.0020 0.6762 0.5921 0.054 Uiso 0.770(4) 1 calc R U P A 1
H31B H -0.0486 0.6084 0.5104 0.054 Uiso 0.770(4) 1 calc R U P A 1
O4A O 0.1009(16) 0.5907(8) 0.5044(7) 0.0429(8) Uani 0.230(4) 1 d D U P A 2
C28A C 0.0919(18) 0.5905(10) 0.4062(9) 0.0427(8) Uani 0.230(4) 1 d D U P A 2
H28B H 0.0011 0.5524 0.4026 0.051 Uiso 0.230(4) 1 calc R U P A 2
C29A C 0.018(2) 0.7073(10) 0.3733(9) 0.0435(8) Uani 0.230(4) 1 d D U P A 2
H29C H 0.0861 0.7257 0.3137 0.052 Uiso 0.230(4) 1 calc R U P A 2
H29D H -0.0982 0.7161 0.3611 0.052 Uiso 0.230(4) 1 calc R U P A 2
C30A C 0.023(2) 0.7787(9) 0.4546(11) 0.0448(8) Uani 0.230(4) 1 d D U P A 2
H30C H -0.0907 0.8204 0.4813 0.054 Uiso 0.230(4) 1 calc R U P A 2
H30D H 0.0928 0.8312 0.4332 0.054 Uiso 0.230(4) 1 calc R U P A 2
C31A C 0.101(2) 0.6988(11) 0.5286(10) 0.0442(8) Uani 0.230(4) 1 d D U P A 2
H31C H 0.2177 0.7037 0.5299 0.053 Uiso 0.230(4) 1 calc R U P A 2
H31D H 0.0367 0.7176 0.5933 0.053 Uiso 0.230(4) 1 calc R U P A 2
Cl1 Cl 0.5296(3) 0.0944(2) 0.93643(18) 0.0667(7) Uani 0.5 1 d . . P . .
C1S C 0.561(2) -0.0440(14) 0.9353(9) 0.042(4) Uani 0.25 1 d . . P . .
H1S1 H 0.6820 -0.0791 0.9202 0.051 Uiso 0.25 1 calc R U P . .
H1S2 H 0.5035 -0.0653 0.8851 0.051 Uiso 0.25 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.388(4) . ?
B1 F2 1.393(4) . ?
B1 N1 1.536(4) . ?
B1 N2 1.545(4) . ?
N1 C1 1.357(4) . ?
N1 C4 1.396(4) . ?
N2 C9 1.345(4) . ?
N2 C6 1.411(4) . ?
O1 C21 1.230(4) . ?
O2 C14 1.448(4) . ?
O2 O3 1.461(3) . ?
O3 C28A 1.280(12) . ?
O3 C28 1.370(6) . ?
C1 C2 1.405(5) . ?
C1 C10 1.499(4) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(4) . ?
C5 C6 1.394(4) . ?
C5 C14 1.536(4) . ?
C6 C7 1.421(4) . ?
C7 C8 1.373(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(4) . ?
C8 H8 0.9500 . ?
C9 C12 1.492(4) . ?
C10 C11 1.524(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.522(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.525(5) . ?
C14 C27 1.525(4) . ?
C15 C16 1.391(5) . ?
C15 C20 1.398(4) . ?
C16 C17 1.390(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.485(5) . ?
C21 C22 1.482(5) . ?
C22 C27 1.394(5) . ?
C22 C23 1.397(5) . ?
C23 C24 1.370(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.396(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(5) . ?
C26 H26 0.9500 . ?
O4 C28 1.406(6) . ?
O4 C31 1.437(5) . ?
C28 C29 1.533(6) . ?
C28 H28 1.0000 . ?
C29 C30 1.563(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.467(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
O4A C28A 1.394(13) . ?
O4A C31A 1.416(13) . ?
C28A C29A 1.523(12) . ?
C28A H28B 1.0000 . ?
C29A C30A 1.496(13) . ?
C29A H29C 0.9900 . ?
C29A H29D 0.9900 . ?
C30A C31A 1.516(12) . ?
C30A H30C 0.9900 . ?
C30A H30D 0.9900 . ?
C31A H31C 0.9900 . ?
C31A H31D 0.9900 . ?
Cl1 C1S 1.694(17) . ?
Cl1 C1S 1.988(12) 2_657 ?
C1S Cl1 1.988(12) 2_657 ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?

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
F1 B1 F2 109.5(3) . . ?
F1 B1 N1 110.3(3) . . ?
F2 B1 N1 110.1(3) . . ?
F1 B1 N2 110.0(3) . . ?
F2 B1 N2 109.6(3) . . ?
N1 B1 N2 107.1(2) . . ?
C1 N1 C4 108.1(3) . . ?
C1 N1 B1 126.6(3) . . ?
C4 N1 B1 125.2(3) . . ?
C9 N2 C6 108.3(3) . . ?
C9 N2 B1 125.7(3) . . ?
C6 N2 B1 125.8(3) . . ?
C14 O2 O3 106.0(2) . . ?
C28A O3 O2 118.2(6) . . ?
C28 O3 O2 105.1(3) . . ?
N1 C1 C2 109.1(3) . . ?
N1 C1 C10 123.3(3) . . ?
C2 C1 C10 127.6(3) . . ?
C3 C2 C1 107.6(3) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
C2 C3 C4 107.5(3) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C5 120.8(3) . . ?
N1 C4 C3 107.7(3) . . ?
C5 C4 C3 131.5(3) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 C14 123.4(3) . . ?
C4 C5 C14 115.4(3) . . ?
C5 C6 N2 119.4(3) . . ?
C5 C6 C7 134.0(3) . . ?
N2 C6 C7 106.5(2) . . ?
C8 C7 C6 108.2(3) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
C7 C8 C9 107.3(3) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
N2 C9 C8 109.6(3) . . ?
N2 C9 C12 122.7(3) . . ?
C8 C9 C12 127.7(3) . . ?
C1 C10 C11 112.9(3) . . ?
C1 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C1 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
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 . . ?
C9 C12 C13 113.7(3) . . ?
C9 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C9 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 106.7(2) . . ?
O2 C14 C27 108.5(3) . . ?
C15 C14 C27 114.5(3) . . ?
O2 C14 C5 105.5(2) . . ?
C15 C14 C5 111.2(3) . . ?
C27 C14 C5 110.0(2) . . ?
C16 C15 C20 118.9(3) . . ?
C16 C15 C14 119.3(3) . . ?
C20 C15 C14 121.5(3) . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.9(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.4(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 119.4(3) . . ?
C19 C20 C21 119.9(3) . . ?
C15 C20 C21 120.7(3) . . ?
O1 C21 C22 121.6(4) . . ?
O1 C21 C20 120.2(4) . . ?
C22 C21 C20 118.2(3) . . ?
C27 C22 C23 119.5(4) . . ?
C27 C22 C21 121.3(3) . . ?
C23 C22 C21 119.2(3) . . ?
C24 C23 C22 120.4(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.4(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.2(3) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 119.8(3) . . ?
C26 C27 C14 118.8(3) . . ?
C22 C27 C14 121.3(3) . . ?
C28 O4 C31 107.3(3) . . ?
O3 C28 O4 112.3(4) . . ?
O3 C28 C29 104.4(4) . . ?
O4 C28 C29 107.6(4) . . ?
O3 C28 H28 110.8 . . ?
O4 C28 H28 110.8 . . ?
C29 C28 H28 110.8 . . ?
C28 C29 C30 103.4(4) . . ?
C28 C29 H29A 111.1 . . ?
C30 C29 H29A 111.1 . . ?
C28 C29 H29B 111.1 . . ?
C30 C29 H29B 111.1 . . ?
H29A C29 H29B 109.1 . . ?
C31 C30 C29 103.6(4) . . ?
C31 C30 H30A 111.0 . . ?
C29 C30 H30A 111.0 . . ?
C31 C30 H30B 111.0 . . ?
C29 C30 H30B 111.0 . . ?
H30A C30 H30B 109.0 . . ?
O4 C31 C30 106.8(4) . . ?
O4 C31 H31A 110.4 . . ?
C30 C31 H31A 110.4 . . ?
O4 C31 H31B 110.4 . . ?
C30 C31 H31B 110.4 . . ?
H31A C31 H31B 108.6 . . ?
C28A O4A C31A 107.3(10) . . ?
O3 C28A O4A 123.8(11) . . ?
O3 C28A C29A 110.9(11) . . ?
O4A C28A C29A 109.2(9) . . ?
O3 C28A H28B 103.5 . . ?
O4A C28A H28B 103.5 . . ?
C29A C28A H28B 103.5 . . ?
C30A C29A C28A 104.9(7) . . ?
C30A C29A H29C 110.8 . . ?
C28A C29A H29C 110.8 . . ?
C30A C29A H29D 110.8 . . ?
C28A C29A H29D 110.8 . . ?
H29C C29A H29D 108.8 . . ?
C29A C30A C31A 104.3(8) . . ?
C29A C30A H30C 110.9 . . ?
C31A C30A H30C 110.9 . . ?
C29A C30A H30D 110.9 . . ?
C31A C30A H30D 110.9 . . ?
H30C C30A H30D 108.9 . . ?
O4A C31A C30A 109.2(9) . . ?
O4A C31A H31C 109.8 . . ?
C30A C31A H31C 109.8 . . ?
O4A C31A H31D 109.8 . . ?
C30A C31A H31D 109.8 . . ?
H31C C31A H31D 108.3 . . ?
C1S Cl1 C1S 70.9(8) . 2_657 ?
Cl1 C1S Cl1 109.1(8) . 2_657 ?
Cl1 C1S H1S1 109.9 . . ?
Cl1 C1S H1S1 109.9 2_657 . ?
Cl1 C1S H1S2 109.9 . . ?
Cl1 C1S H1S2 109.9 2_657 . ?
H1S1 C1S H1S2 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 B1 N1 C1 -59.0(4) . . . . ?
F2 B1 N1 C1 62.0(4) . . . . ?
N2 B1 N1 C1 -178.8(3) . . . . ?
F1 B1 N1 C4 125.1(3) . . . . ?
F2 B1 N1 C4 -113.8(3) . . . . ?
N2 B1 N1 C4 5.4(4) . . . . ?
F1 B1 N2 C9 57.8(4) . . . . ?
F2 B1 N2 C9 -62.8(4) . . . . ?
N1 B1 N2 C9 177.7(3) . . . . ?
F1 B1 N2 C6 -127.2(3) . . . . ?
F2 B1 N2 C6 112.2(3) . . . . ?
N1 B1 N2 C6 -7.3(4) . . . . ?
C14 O2 O3 C28A 170.8(8) . . . . ?
C14 O2 O3 C28 -124.0(3) . . . . ?
C4 N1 C1 C2 -0.5(4) . . . . ?
B1 N1 C1 C2 -176.9(3) . . . . ?
C4 N1 C1 C10 179.8(3) . . . . ?
B1 N1 C1 C10 3.3(5) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
C10 C1 C2 C3 -179.9(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 N1 C4 C5 -178.3(3) . . . . ?
B1 N1 C4 C5 -1.8(4) . . . . ?
C1 N1 C4 C3 0.5(3) . . . . ?
B1 N1 C4 C3 177.0(3) . . . . ?
C2 C3 C4 N1 -0.3(4) . . . . ?
C2 C3 C4 C5 178.3(3) . . . . ?
N1 C4 C5 C6 -1.1(4) . . . . ?
C3 C4 C5 C6 -179.5(3) . . . . ?
N1 C4 C5 C14 179.1(3) . . . . ?
C3 C4 C5 C14 0.6(5) . . . . ?
C4 C5 C6 N2 -0.7(4) . . . . ?
C14 C5 C6 N2 179.2(3) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C14 C5 C6 C7 -0.3(5) . . . . ?
C9 N2 C6 C5 -178.8(3) . . . . ?
B1 N2 C6 C5 5.5(4) . . . . ?
C9 N2 C6 C7 0.8(3) . . . . ?
B1 N2 C6 C7 -174.9(3) . . . . ?
C5 C6 C7 C8 179.0(3) . . . . ?
N2 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C6 N2 C9 C8 -0.7(3) . . . . ?
B1 N2 C9 C8 175.0(3) . . . . ?
C6 N2 C9 C12 179.4(3) . . . . ?
B1 N2 C9 C12 -4.9(4) . . . . ?
C7 C8 C9 N2 0.4(4) . . . . ?
C7 C8 C9 C12 -179.7(3) . . . . ?
N1 C1 C10 C11 92.8(4) . . . . ?
C2 C1 C10 C11 -86.9(4) . . . . ?
N2 C9 C12 C13 173.4(3) . . . . ?
C8 C9 C12 C13 -6.5(5) . . . . ?
O3 O2 C14 C15 -58.6(3) . . . . ?
O3 O2 C14 C27 65.2(3) . . . . ?
O3 O2 C14 C5 -177.0(2) . . . . ?
C6 C5 C14 O2 -1.6(4) . . . . ?
C4 C5 C14 O2 178.2(3) . . . . ?
C6 C5 C14 C15 -117.0(3) . . . . ?
C4 C5 C14 C15 62.9(3) . . . . ?
C6 C5 C14 C27 115.2(3) . . . . ?
C4 C5 C14 C27 -65.0(3) . . . . ?
O2 C14 C15 C16 -69.8(4) . . . . ?
C27 C14 C15 C16 170.1(3) . . . . ?
C5 C14 C15 C16 44.7(4) . . . . ?
O2 C14 C15 C20 104.1(3) . . . . ?
C27 C14 C15 C20 -16.1(4) . . . . ?
C5 C14 C15 C20 -141.4(3) . . . . ?
C20 C15 C16 C17 0.5(6) . . . . ?
C14 C15 C16 C17 174.5(3) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 C19 -1.0(7) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C18 C19 C20 C15 -0.2(6) . . . . ?
C18 C19 C20 C21 -179.4(4) . . . . ?
C16 C15 C20 C19 -0.6(5) . . . . ?
C14 C15 C20 C19 -174.4(3) . . . . ?
C16 C15 C20 C21 178.6(3) . . . . ?
C14 C15 C20 C21 4.8(5) . . . . ?
C19 C20 C21 O1 6.3(6) . . . . ?
C15 C20 C21 O1 -172.9(4) . . . . ?
C19 C20 C21 C22 -172.9(3) . . . . ?
C15 C20 C21 C22 7.9(5) . . . . ?
O1 C21 C22 C27 172.4(4) . . . . ?
C20 C21 C22 C27 -8.5(5) . . . . ?
O1 C21 C22 C23 -7.1(6) . . . . ?
C20 C21 C22 C23 172.0(3) . . . . ?
C27 C22 C23 C24 0.9(6) . . . . ?
C21 C22 C23 C24 -179.6(4) . . . . ?
C22 C23 C24 C25 -1.6(6) . . . . ?
C23 C24 C25 C26 0.8(6) . . . . ?
C24 C25 C26 C27 0.7(6) . . . . ?
C25 C26 C27 C22 -1.3(5) . . . . ?
C25 C26 C27 C14 -176.7(3) . . . . ?
C23 C22 C27 C26 0.5(5) . . . . ?
C21 C22 C27 C26 -178.9(3) . . . . ?
C23 C22 C27 C14 175.8(3) . . . . ?
C21 C22 C27 C14 -3.7(5) . . . . ?
O2 C14 C27 C26 71.6(3) . . . . ?
C15 C14 C27 C26 -169.3(3) . . . . ?
C5 C14 C27 C26 -43.2(4) . . . . ?
O2 C14 C27 C22 -103.6(3) . . . . ?
C15 C14 C27 C22 15.5(4) . . . . ?
C5 C14 C27 C22 141.5(3) . . . . ?
O2 O3 C28 O4 -61.6(4) . . . . ?
O2 O3 C28 C29 -177.8(3) . . . . ?
C31 O4 C28 O3 -89.0(4) . . . . ?
C31 O4 C28 C29 25.4(5) . . . . ?
O3 C28 C29 C30 113.1(4) . . . . ?
O4 C28 C29 C30 -6.4(5) . . . . ?
C28 C29 C30 C31 -14.1(5) . . . . ?
C28 O4 C31 C30 -35.5(5) . . . . ?
C29 C30 C31 O4 29.8(6) . . . . ?
O2 O3 C28A O4A 32.5(16) . . . . ?
O2 O3 C28A C29A 165.3(8) . . . . ?
C31A O4A C28A O3 111.2(15) . . . . ?
C31A O4A C28A C29A -22.2(18) . . . . ?
O3 C28A C29A C30A -126.6(14) . . . . ?
O4A C28A C29A C30A 13.1(18) . . . . ?
C28A C29A C30A C31A 0.6(18) . . . . ?
C28A O4A C31A C30A 22.7(18) . . . . ?
C29A C30A C31A O4A -14.0(19) . . . . ?
C1S Cl1 C1S Cl1 0.001(2) 2_657 . . 2_657 ?

_refine_diff_density_max         1.130
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.100

