# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_wa2145
_database_code_depnum_ccdc_archive 'CCDC 1420444'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H15 B F2 I2'
_chemical_formula_sum            'C26 H15 B F2 I2'
_chemical_formula_weight         629.99

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'
B B 0.0013 0.0007 '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'
I I -0.4742 1.8119 '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                   20.082(3)
_cell_length_b                   9.3614(8)
_cell_length_c                   14.7770(18)
_cell_angle_alpha                90
_cell_angle_beta                 126.854(8)
_cell_angle_gamma                90
_cell_volume                     2222.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5525
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      25.94

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.857
_shelx_estimated_absorpt_T_min   0.502
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.460
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15809
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.446
_diffrn_reflns_theta_max         25.807
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9924
_reflns_number_gt                7834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1077P)²] 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         9924
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
I1 I 0.34640(4) 0.45432(7) 0.48575(5) 0.0408(3) Uani 1 1 d . . . . .
F1 F 0.5736(3) 0.3497(6) 0.6722(5) 0.0409(12) Uani 1 1 d . . . . .
B1 B 0.5000 0.5331(13) 0.7500 0.027(3) Uani 1 2 d S T P . .
C1 C 0.5000 0.3641(11) 0.7500 0.025(2) Uani 1 2 d S T P . .
C2 C 0.5376(5) 0.2814(9) 0.7132(7) 0.0282(17) Uani 1 1 d . . . . .
C3 C 0.5387(5) 0.1319(9) 0.7124(7) 0.0333(18) Uani 1 1 d . . . . .
H3 H 0.5656 0.0818 0.6865 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5000 0.0593(12) 0.7500 0.034(3) Uani 1 2 d S T P . .
H4 H 0.5000 -0.0422 0.7500 0.041 Uiso 1 2 calc R U P . .
C11 C 0.4309(5) 0.6218(8) 0.7438(7) 0.0251(16) Uani 1 1 d . . . . .
C12 C 0.3416(5) 0.6090(8) 0.6691(7) 0.0261(16) Uani 1 1 d . . . . .
C13 C 0.2933(5) 0.5308(9) 0.5641(8) 0.0340(19) Uani 1 1 d . . . . .
C14 C 0.2095(6) 0.5127(11) 0.5024(9) 0.043(2) Uani 1 1 d . . . . .
H14 H 0.1808 0.4573 0.4351 0.052 Uiso 1 1 calc R U . . .
C15 C 0.1655(6) 0.5757(11) 0.5383(9) 0.045(2) Uani 1 1 d . . . . .
H15 H 0.1075 0.5587 0.4973 0.054 Uiso 1 1 calc R U . . .
C16 C 0.2053(6) 0.6604(10) 0.6307(9) 0.042(2) Uani 1 1 d . . . . .
H16 H 0.1743 0.7072 0.6514 0.051 Uiso 1 1 calc R U . . .
C17 C 0.2932(5) 0.6808(9) 0.6976(8) 0.0305(18) Uani 1 1 d . . . . .
C18 C 0.3329(6) 0.7717(9) 0.7930(9) 0.037(2) Uani 1 1 d . . . . .
H18 H 0.3006 0.8213 0.8103 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4171(6) 0.7887(9) 0.8603(8) 0.037(2) Uani 1 1 d . . . . .
H19 H 0.4432 0.8502 0.9241 0.044 Uiso 1 1 calc R U . . .
C20 C 0.4651(5) 0.7155(9) 0.8352(7) 0.0302(17) Uani 1 1 d . . . . .
H20 H 0.5236 0.7303 0.8825 0.036 Uiso 1 1 calc R 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
I1 C13 2.115(9) . ?
F1 C2 1.351(10) . ?
B1 C11 1.572(10) 2_656 ?
B1 C11 1.572(10) . ?
B1 C1 1.582(15) . ?
C1 C2 1.398(10) 2_656 ?
C1 C2 1.398(10) . ?
C2 C3 1.401(12) . ?
C3 C4 1.376(11) . ?
C3 H3 0.9500 . ?
C4 C3 1.376(11) 2_656 ?
C4 H4 0.9500 . ?
C11 C20 1.398(11) . ?
C11 C12 1.441(11) . ?
C12 C17 1.437(11) . ?
C12 C13 1.442(12) . ?
C13 C14 1.360(13) . ?
C14 C15 1.404(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.351(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.427(13) . ?
C16 H16 0.9500 . ?
C17 C18 1.413(13) . ?
C18 C19 1.362(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.402(12) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 B1 C11 116.2(9) 2_656 . ?
C11 B1 C1 121.9(5) 2_656 . ?
C11 B1 C1 121.9(5) . . ?
C2 C1 C2 112.8(10) 2_656 . ?
C2 C1 B1 123.6(5) 2_656 . ?
C2 C1 B1 123.6(5) . . ?
F1 C2 C1 118.1(7) . . ?
F1 C2 C3 116.9(7) . . ?
C1 C2 C3 124.9(8) . . ?
C4 C3 C2 118.2(8) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C3 120.9(11) . 2_656 ?
C3 C4 H4 119.6 . . ?
C3 C4 H4 119.6 2_656 . ?
C20 C11 C12 117.2(7) . . ?
C20 C11 B1 111.7(6) . . ?
C12 C11 B1 130.6(7) . . ?
C17 C12 C11 119.1(7) . . ?
C17 C12 C13 114.6(7) . . ?
C11 C12 C13 126.3(7) . . ?
C14 C13 C12 123.2(9) . . ?
C14 C13 I1 114.7(7) . . ?
C12 C13 I1 121.7(5) . . ?
C13 C14 C15 120.0(10) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.2(9) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.0(8) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.7(8) . . ?
C18 C17 C12 119.8(7) . . ?
C16 C17 C12 120.5(8) . . ?
C19 C18 C17 120.6(8) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.9(8) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C11 C20 C19 123.0(8) . . ?
C11 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 B1 C1 C2 154.9(5) 2_656 . . 2_656 ?
C11 B1 C1 C2 -25.1(5) . . . 2_656 ?
C11 B1 C1 C2 -25.1(5) 2_656 . . . ?
C11 B1 C1 C2 154.9(5) . . . . ?
C2 C1 C2 F1 177.9(8) 2_656 . . . ?
B1 C1 C2 F1 -2.1(8) . . . . ?
C2 C1 C2 C3 -0.1(6) 2_656 . . . ?
B1 C1 C2 C3 179.9(6) . . . . ?
F1 C2 C3 C4 -177.8(6) . . . . ?
C1 C2 C3 C4 0.3(11) . . . . ?
C2 C3 C4 C3 -0.1(5) . . . 2_656 ?
C11 B1 C11 C20 -56.8(5) 2_656 . . . ?
C1 B1 C11 C20 123.2(5) . . . . ?
C11 B1 C11 C12 131.4(9) 2_656 . . . ?
C1 B1 C11 C12 -48.6(9) . . . . ?
C20 C11 C12 C17 -6.1(11) . . . . ?
B1 C11 C12 C17 165.4(8) . . . . ?
C20 C11 C12 C13 173.1(8) . . . . ?
B1 C11 C12 C13 -15.5(13) . . . . ?
C17 C12 C13 C14 -6.8(12) . . . . ?
C11 C12 C13 C14 174.0(9) . . . . ?
C17 C12 C13 I1 166.5(6) . . . . ?
C11 C12 C13 I1 -12.7(11) . . . . ?
C12 C13 C14 C15 2.2(15) . . . . ?
I1 C13 C14 C15 -171.5(8) . . . . ?
C13 C14 C15 C16 3.4(15) . . . . ?
C14 C15 C16 C17 -3.9(14) . . . . ?
C15 C16 C17 C18 179.1(9) . . . . ?
C15 C16 C17 C12 -1.1(13) . . . . ?
C11 C12 C17 C18 5.1(11) . . . . ?
C13 C12 C17 C18 -174.1(8) . . . . ?
C11 C12 C17 C16 -174.6(7) . . . . ?
C13 C12 C17 C16 6.1(11) . . . . ?
C16 C17 C18 C19 177.7(8) . . . . ?
C12 C17 C18 C19 -2.0(13) . . . . ?
C17 C18 C19 C20 -0.1(14) . . . . ?
C12 C11 C20 C19 4.2(13) . . . . ?
B1 C11 C20 C19 -168.8(8) . . . . ?
C18 C19 C20 C11 -1.1(14) . . . . ?

_refine_diff_density_max         1.055
_refine_diff_density_min         -1.584
_refine_diff_density_rms         0.155

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_wa2129
_database_code_depnum_ccdc_archive 'CCDC 1420445'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H15 B Br4'
_chemical_formula_sum            'C26 H15 B Br4'
_chemical_formula_weight         657.83

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6333(9)
_cell_length_b                   14.6789(7)
_cell_length_c                   12.1639(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.908(6)
_cell_angle_gamma                90
_cell_volume                     2247.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    26415
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      29.87

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    7.175
_shelx_estimated_absorpt_T_min   0.343
_shelx_estimated_absorpt_T_max   0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29288
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.213
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4584
_reflns_number_gt                3822
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²] 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         4584
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.86806(4) 0.37919(3) 0.38355(4) 0.02946(14) Uani 1 1 d . . . . .
Br2 Br 0.67802(4) 0.73635(3) 0.28471(4) 0.02337(12) Uani 1 1 d . . . . .
Br3 Br 0.91795(4) 0.66806(3) 0.17949(4) 0.02567(13) Uani 1 1 d . . . . .
Br4 Br 0.57908(5) 0.39962(3) 0.33972(5) 0.03233(14) Uani 1 1 d . . . . .
B1 B 0.7345(4) 0.5252(3) 0.2135(4) 0.0184(10) Uani 1 1 d . . . . .
C1 C 0.7685(4) 0.5566(3) 0.3373(4) 0.0197(9) Uani 1 1 d . . . . .
C2 C 0.8257(4) 0.5009(3) 0.4165(4) 0.0211(9) Uani 1 1 d . . . . .
C3 C 0.8529(4) 0.5270(4) 0.5247(4) 0.0287(11) Uani 1 1 d . . . . .
H3 H 0.8923 0.4870 0.5742 0.034 Uiso 1 1 calc R U . . .
C4 C 0.8221(5) 0.6118(4) 0.5601(4) 0.0322(12) Uani 1 1 d . . . . .
H4 H 0.8387 0.6297 0.6347 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7673(5) 0.6705(4) 0.4871(4) 0.0286(11) Uani 1 1 d . . . . .
H5 H 0.7467 0.7291 0.5107 0.034 Uiso 1 1 calc R U . . .
C6 C 0.7427(4) 0.6430(3) 0.3790(4) 0.0190(9) Uani 1 1 d . . . . .
C11 C 0.8105(4) 0.4664(3) 0.1459(4) 0.0192(9) Uani 1 1 d . . . . .
C12 C 0.9249(4) 0.4732(3) 0.1442(4) 0.0201(9) Uani 1 1 d . . . . .
C13 C 0.9864(4) 0.5534(3) 0.1654(4) 0.0204(9) Uani 1 1 d . . . . .
C14 C 1.0952(4) 0.5549(3) 0.1698(4) 0.0249(10) Uani 1 1 d . . . . .
H14 H 1.1330 0.6098 0.1864 0.030 Uiso 1 1 calc R U . . .
C15 C 1.1504(4) 0.4741(4) 0.1493(4) 0.0297(11) Uani 1 1 d . . . . .
H15 H 1.2259 0.4737 0.1559 0.036 Uiso 1 1 calc R U . . .
C16 C 1.0960(4) 0.3966(4) 0.1202(4) 0.0260(11) Uani 1 1 d . . . . .
H16 H 1.1337 0.3434 0.1022 0.031 Uiso 1 1 calc R U . . .
C17 C 0.9837(4) 0.3945(3) 0.1164(4) 0.0220(10) Uani 1 1 d . . . . .
C18 C 0.9281(4) 0.3136(3) 0.0822(4) 0.0276(11) Uani 1 1 d . . . . .
H18 H 0.9671 0.2605 0.0664 0.033 Uiso 1 1 calc R U . . .
C19 C 0.8201(5) 0.3111(3) 0.0718(4) 0.0294(11) Uani 1 1 d . . . . .
H19 H 0.7840 0.2583 0.0430 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7616(4) 0.3875(3) 0.1041(4) 0.0244(10) Uani 1 1 d . . . . .
H20 H 0.6862 0.3846 0.0969 0.029 Uiso 1 1 calc R U . . .
C21 C 0.6217(4) 0.5508(3) 0.1575(4) 0.0191(9) Uani 1 1 d . . . . .
C22 C 0.5252(4) 0.5606(3) 0.2118(4) 0.0206(9) Uani 1 1 d . . . . .
C23 C 0.5000(4) 0.5073(3) 0.3034(4) 0.0241(10) Uani 1 1 d . . . . .
C24 C 0.4135(4) 0.5255(4) 0.3626(5) 0.0308(11) Uani 1 1 d . . . . .
H24 H 0.4001 0.4893 0.4247 0.037 Uiso 1 1 calc R U . . .
C25 C 0.3464(5) 0.5978(4) 0.3298(5) 0.0387(13) Uani 1 1 d . . . . .
H25 H 0.2901 0.6136 0.3732 0.046 Uiso 1 1 calc R U . . .
C26 C 0.3606(4) 0.6464(4) 0.2359(5) 0.0320(12) Uani 1 1 d . . . . .
H26 H 0.3120 0.6933 0.2125 0.038 Uiso 1 1 calc R U . . .
C27 C 0.4478(4) 0.6265(3) 0.1736(4) 0.0229(10) Uani 1 1 d . . . . .
C28 C 0.4590(4) 0.6711(3) 0.0720(4) 0.0270(11) Uani 1 1 d . . . . .
H28 H 0.4084 0.7158 0.0463 0.032 Uiso 1 1 calc R U . . .
C29 C 0.5405(4) 0.6512(3) 0.0108(4) 0.0272(11) Uani 1 1 d . . . . .
H29 H 0.5421 0.6765 -0.0609 0.033 Uiso 1 1 calc R U . . .
C30 C 0.6232(4) 0.5929(3) 0.0532(4) 0.0202(9) Uani 1 1 d . . . . .
H30 H 0.6813 0.5817 0.0104 0.024 Uiso 1 1 calc R 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
Br1 C2 1.917(5) . ?
Br2 C6 1.923(5) . ?
Br3 C13 1.907(5) . ?
Br4 C23 1.902(5) . ?
B1 C21 1.572(7) . ?
B1 C11 1.575(7) . ?
B1 C1 1.598(7) . ?
C1 C2 1.414(6) . ?
C1 C6 1.415(6) . ?
C2 C3 1.386(7) . ?
C3 C4 1.384(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(7) . ?
C5 H5 0.9500 . ?
C11 C20 1.389(7) . ?
C11 C12 1.450(7) . ?
C12 C13 1.421(7) . ?
C12 C17 1.430(6) . ?
C13 C14 1.372(7) . ?
C14 C15 1.409(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.360(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.416(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.424(7) . ?
C18 C19 1.360(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.418(7) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C30 1.413(7) . ?
C21 C22 1.442(7) . ?
C22 C23 1.420(7) . ?
C22 C27 1.425(7) . ?
C23 C24 1.384(7) . ?
C24 C25 1.396(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.371(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.420(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.416(7) . ?
C28 C29 1.352(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.413(7) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 B1 C11 118.4(4) . . ?
C21 B1 C1 120.0(4) . . ?
C11 B1 C1 121.6(4) . . ?
C2 C1 C6 113.3(4) . . ?
C2 C1 B1 123.8(4) . . ?
C6 C1 B1 123.0(4) . . ?
C3 C2 C1 123.9(4) . . ?
C3 C2 Br1 113.9(4) . . ?
C1 C2 Br1 122.1(3) . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.3(5) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 124.2(5) . . ?
C5 C6 Br2 114.1(4) . . ?
C1 C6 Br2 121.6(3) . . ?
C20 C11 C12 117.8(4) . . ?
C20 C11 B1 112.1(4) . . ?
C12 C11 B1 128.5(4) . . ?
C13 C12 C17 115.2(4) . . ?
C13 C12 C11 125.7(4) . . ?
C17 C12 C11 119.1(4) . . ?
C14 C13 C12 123.4(4) . . ?
C14 C13 Br3 116.3(4) . . ?
C12 C13 Br3 120.2(3) . . ?
C13 C14 C15 119.3(5) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.6(5) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 119.7(5) . . ?
C16 C17 C12 121.0(5) . . ?
C18 C17 C12 119.3(4) . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.7(5) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C11 C20 C19 122.3(5) . . ?
C11 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C30 C21 C22 116.4(4) . . ?
C30 C21 B1 114.3(4) . . ?
C22 C21 B1 126.6(4) . . ?
C23 C22 C27 115.9(4) . . ?
C23 C22 C21 124.1(4) . . ?
C27 C22 C21 120.1(4) . . ?
C24 C23 C22 122.8(5) . . ?
C24 C23 Br4 117.5(4) . . ?
C22 C23 Br4 119.4(4) . . ?
C23 C24 C25 119.0(5) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 121.0(5) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 120.1(5) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.8(5) . . ?
C28 C27 C22 118.8(5) . . ?
C26 C27 C22 120.5(5) . . ?
C29 C28 C27 121.2(5) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 120.3(5) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C21 C30 C29 121.7(5) . . ?
C21 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?

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
C21 B1 C1 C2 139.5(5) . . . . ?
C11 B1 C1 C2 -38.9(7) . . . . ?
C21 B1 C1 C6 -39.6(6) . . . . ?
C11 B1 C1 C6 142.0(5) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
B1 C1 C2 C3 -178.2(5) . . . . ?
C6 C1 C2 Br1 178.5(3) . . . . ?
B1 C1 C2 Br1 -0.7(7) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
Br1 C2 C3 C4 -176.9(4) . . . . ?
C2 C3 C4 C5 -1.7(8) . . . . ?
C3 C4 C5 C6 0.8(8) . . . . ?
C4 C5 C6 C1 1.1(8) . . . . ?
C4 C5 C6 Br2 -174.6(4) . . . . ?
C2 C1 C6 C5 -1.9(7) . . . . ?
B1 C1 C6 C5 177.2(5) . . . . ?
C2 C1 C6 Br2 173.5(3) . . . . ?
B1 C1 C6 Br2 -7.3(6) . . . . ?
C21 B1 C11 C20 -52.4(6) . . . . ?
C1 B1 C11 C20 126.0(5) . . . . ?
C21 B1 C11 C12 142.9(5) . . . . ?
C1 B1 C11 C12 -38.7(7) . . . . ?
C20 C11 C12 C13 168.7(4) . . . . ?
B1 C11 C12 C13 -27.4(7) . . . . ?
C20 C11 C12 C17 -9.6(6) . . . . ?
B1 C11 C12 C17 154.3(4) . . . . ?
C17 C12 C13 C14 -6.0(7) . . . . ?
C11 C12 C13 C14 175.7(5) . . . . ?
C17 C12 C13 Br3 169.6(3) . . . . ?
C11 C12 C13 Br3 -8.7(6) . . . . ?
C12 C13 C14 C15 1.9(7) . . . . ?
Br3 C13 C14 C15 -173.9(4) . . . . ?
C13 C14 C15 C16 3.3(8) . . . . ?
C14 C15 C16 C17 -3.8(8) . . . . ?
C15 C16 C17 C18 177.9(5) . . . . ?
C15 C16 C17 C12 -0.7(7) . . . . ?
C13 C12 C17 C16 5.3(6) . . . . ?
C11 C12 C17 C16 -176.2(4) . . . . ?
C13 C12 C17 C18 -173.3(4) . . . . ?
C11 C12 C17 C18 5.2(7) . . . . ?
C16 C17 C18 C19 -176.3(5) . . . . ?
C12 C17 C18 C19 2.4(7) . . . . ?
C17 C18 C19 C20 -5.3(8) . . . . ?
C12 C11 C20 C19 6.9(7) . . . . ?
B1 C11 C20 C19 -159.5(5) . . . . ?
C18 C19 C20 C11 0.5(8) . . . . ?
C11 B1 C21 C30 -53.1(6) . . . . ?
C1 B1 C21 C30 128.5(4) . . . . ?
C11 B1 C21 C22 146.3(4) . . . . ?
C1 B1 C21 C22 -32.2(7) . . . . ?
C30 C21 C22 C23 165.3(4) . . . . ?
B1 C21 C22 C23 -34.3(7) . . . . ?
C30 C21 C22 C27 -14.3(6) . . . . ?
B1 C21 C22 C27 146.0(5) . . . . ?
C27 C22 C23 C24 -8.7(7) . . . . ?
C21 C22 C23 C24 171.7(5) . . . . ?
C27 C22 C23 Br4 165.3(3) . . . . ?
C21 C22 C23 Br4 -14.3(6) . . . . ?
C22 C23 C24 C25 1.6(8) . . . . ?
Br4 C23 C24 C25 -172.5(4) . . . . ?
C23 C24 C25 C26 4.7(8) . . . . ?
C24 C25 C26 C27 -3.3(8) . . . . ?
C25 C26 C27 C28 175.1(5) . . . . ?
C25 C26 C27 C22 -4.3(8) . . . . ?
C23 C22 C27 C28 -169.5(4) . . . . ?
C21 C22 C27 C28 10.2(7) . . . . ?
C23 C22 C27 C26 9.9(7) . . . . ?
C21 C22 C27 C26 -170.4(4) . . . . ?
C26 C27 C28 C29 -178.5(5) . . . . ?
C22 C27 C28 C29 0.9(7) . . . . ?
C27 C28 C29 C30 -7.3(8) . . . . ?
C22 C21 C30 C29 8.0(7) . . . . ?
B1 C21 C30 C29 -154.7(4) . . . . ?
C28 C29 C30 C21 2.7(7) . . . . ?

_refine_diff_density_max         1.081
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.123

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_wa2021
_database_code_depnum_ccdc_archive 'CCDC 1420446'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H15 B'
_chemical_formula_sum            'C26 H15 B'
_chemical_formula_weight         338.19

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.9791(12)
_cell_length_b                   19.948(6)
_cell_length_c                   20.208(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1604.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2443
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      25.4

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7082
_diffrn_reflns_av_unetI/netI     0.2106
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         25.735
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2966
_reflns_number_gt                1172
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_max     0.951
_reflns_Friedel_fraction_full    0.975

_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0211P)²] 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     SHELXL
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 269 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -10.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2966
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1732
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   0.844
_refine_ls_restrained_S_all      0.844
_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 0.231(2) 0.6337(4) 0.6761(5) 0.033(2) Uani 1 1 d . . . . .
C1 C 0.3932(19) 0.5795(4) 0.7198(4) 0.0312(19) Uani 1 1 d . . . . .
C2 C 0.499(2) 0.5180(4) 0.6902(5) 0.037(2) Uani 1 1 d . . . . .
C3 C 0.665(2) 0.4703(4) 0.7306(4) 0.041(2) Uani 1 1 d . . . . .
H3 H 0.7394 0.4292 0.7118 0.049 Uiso 1 1 calc R U . . .
C4 C 0.718(2) 0.4827(4) 0.7960(4) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.8311 0.4502 0.8222 0.054 Uiso 1 1 calc R U . . .
C5 C 0.612(2) 0.5414(4) 0.8248(5) 0.043(2) Uani 1 1 d . . . . .
H5 H 0.6492 0.5486 0.8707 0.051 Uiso 1 1 calc R U . . .
C6 C 0.450(2) 0.5908(4) 0.7875(5) 0.039(2) Uani 1 1 d . . . . .
C11 C 0.239(2) 0.6224(4) 0.6011(4) 0.037(2) Uani 1 1 d . . . . .
C12 C 0.325(2) 0.5565(4) 0.5760(4) 0.0326(19) Uani 1 1 d . . . . .
C13 C 0.4444(18) 0.5050(4) 0.6194(4) 0.0330(19) Uani 1 1 d . . . . .
C14 C 0.517(2) 0.4430(4) 0.5919(5) 0.045(2) Uani 1 1 d . . . . .
H14 H 0.5965 0.4083 0.6201 0.054 Uiso 1 1 calc R U . . .
C15 C 0.479(2) 0.4291(4) 0.5249(5) 0.048(2) Uani 1 1 d . . . . .
H15 H 0.5238 0.3853 0.5086 0.058 Uiso 1 1 calc R U . . .
C16 C 0.378(2) 0.4786(4) 0.4823(5) 0.049(2) Uani 1 1 d . . . . .
H16 H 0.3580 0.4698 0.4363 0.059 Uiso 1 1 calc R U . . .
C17 C 0.304(2) 0.5431(4) 0.5079(4) 0.042(2) Uani 1 1 d . . . . .
C18 C 0.212(2) 0.5951(4) 0.4639(4) 0.047(2) Uani 1 1 d . . . . .
H18 H 0.1892 0.5852 0.4181 0.057 Uiso 1 1 calc R U . . .
C19 C 0.156(3) 0.6597(5) 0.4855(5) 0.055(2) Uani 1 1 d . . . . .
H19 H 0.1089 0.6949 0.4553 0.066 Uiso 1 1 calc R U . . .
C20 C 0.170(2) 0.6715(4) 0.5540(5) 0.044(2) Uani 1 1 d . . . . .
H20 H 0.1304 0.7159 0.5692 0.053 Uiso 1 1 calc R U . . .
C21 C 0.0741(19) 0.6956(4) 0.7134(4) 0.033(2) Uani 1 1 d . . . . .
C22 C 0.150(2) 0.7039(4) 0.7829(4) 0.035(2) Uani 1 1 d . . . . .
C23 C 0.332(2) 0.6542(4) 0.8184(4) 0.038(2) Uani 1 1 d . . . . .
C24 C 0.402(2) 0.6666(4) 0.8846(5) 0.049(2) Uani 1 1 d . . . . .
H24 H 0.5293 0.6346 0.9088 0.059 Uiso 1 1 calc R U . . .
C25 C 0.291(2) 0.7257(4) 0.9175(5) 0.053(3) Uani 1 1 d . . . . .
H25 H 0.3439 0.7327 0.9628 0.064 Uiso 1 1 calc R U . . .
C26 C 0.105(2) 0.7728(4) 0.8831(5) 0.048(2) Uani 1 1 d . . . . .
H26 H 0.0246 0.8117 0.9051 0.058 Uiso 1 1 calc R U . . .
C27 C 0.036(2) 0.7633(4) 0.8158(5) 0.044(2) Uani 1 1 d . . . . .
C28 C -0.151(2) 0.8117(4) 0.7803(5) 0.044(2) Uani 1 1 d . . . . .
H28 H -0.2165 0.8519 0.8019 0.053 Uiso 1 1 calc R U . . .
C29 C -0.239(2) 0.8019(4) 0.7152(4) 0.041(2) Uani 1 1 d . . . . .
H29 H -0.3702 0.8341 0.6923 0.050 Uiso 1 1 calc R U . . .
C30 C -0.130(2) 0.7436(4) 0.6838(5) 0.038(2) Uani 1 1 d . . . . .
H30 H -0.1996 0.7362 0.6394 0.046 Uiso 1 1 calc R 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
B1 C11 1.532(13) . ?
B1 C1 1.538(12) . ?
B1 C21 1.576(11) . ?
C1 C6 1.405(12) . ?
C1 C2 1.429(10) . ?
C2 C3 1.416(11) . ?
C2 C13 1.470(12) . ?
C3 C4 1.361(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(12) . ?
C5 H5 0.9500 . ?
C6 C23 1.486(11) . ?
C11 C20 1.393(11) . ?
C11 C12 1.452(10) . ?
C12 C17 1.404(12) . ?
C12 C13 1.431(11) . ?
C13 C14 1.388(11) . ?
C14 C15 1.391(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.370(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.417(10) . ?
C16 H16 0.9500 . ?
C17 C18 1.414(11) . ?
C18 C19 1.381(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.404(12) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C30 1.391(11) . ?
C21 C22 1.446(12) . ?
C22 C23 1.422(12) . ?
C22 C27 1.433(11) . ?
C23 C24 1.390(13) . ?
C24 C25 1.423(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(13) . ?
C25 H25 0.9500 . ?
C26 C27 1.401(14) . ?
C26 H26 0.9500 . ?
C27 C28 1.412(12) . ?
C28 C29 1.374(12) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(11) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 B1 C1 117.1(7) . . ?
C11 B1 C21 126.6(8) . . ?
C1 B1 C21 116.2(8) . . ?
C6 C1 C2 119.8(8) . . ?
C6 C1 B1 121.0(7) . . ?
C2 C1 B1 119.2(8) . . ?
C3 C2 C1 118.3(8) . . ?
C3 C2 C13 120.7(7) . . ?
C1 C2 C13 120.9(8) . . ?
C4 C3 C2 120.6(8) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.3(9) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 120.9(9) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.2(8) . . ?
C5 C6 C23 121.2(8) . . ?
C1 C6 C23 119.6(8) . . ?
C20 C11 C12 116.4(8) . . ?
C20 C11 B1 124.7(7) . . ?
C12 C11 B1 118.9(7) . . ?
C17 C12 C13 119.0(7) . . ?
C17 C12 C11 120.0(7) . . ?
C13 C12 C11 120.9(8) . . ?
C14 C13 C12 117.6(8) . . ?
C14 C13 C2 121.1(8) . . ?
C12 C13 C2 121.3(7) . . ?
C13 C14 C15 123.1(9) . . ?
C13 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
C16 C15 C14 120.0(8) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.1(9) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C18 119.5(7) . . ?
C12 C17 C16 121.1(8) . . ?
C18 C17 C16 119.3(8) . . ?
C19 C18 C17 121.8(8) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 117.5(8) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C11 C20 C19 124.3(8) . . ?
C11 C20 H20 117.8 . . ?
C19 C20 H20 117.8 . . ?
C30 C21 C22 117.5(7) . . ?
C30 C21 B1 124.4(8) . . ?
C22 C21 B1 118.1(7) . . ?
C23 C22 C27 120.4(8) . . ?
C23 C22 C21 121.1(7) . . ?
C27 C22 C21 118.6(8) . . ?
C24 C23 C22 117.5(8) . . ?
C24 C23 C6 119.6(8) . . ?
C22 C23 C6 122.9(8) . . ?
C23 C24 C25 122.4(10) . . ?
C23 C24 H24 118.8 . . ?
C25 C24 H24 118.8 . . ?
C26 C25 C24 119.6(10) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.1(9) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 120.3(8) . . ?
C26 C27 C22 120.0(8) . . ?
C28 C27 C22 119.8(9) . . ?
C29 C28 C27 121.5(8) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C28 C29 C30 118.4(8) . . ?
C28 C29 H29 120.8 . . ?
C30 C29 H29 120.8 . . ?
C21 C30 C29 124.0(9) . . ?
C21 C30 H30 118.0 . . ?
C29 C30 H30 118.0 . . ?

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
C11 B1 C1 C6 168.8(8) . . . . ?
C21 B1 C1 C6 -11.0(10) . . . . ?
C11 B1 C1 C2 -8.6(11) . . . . ?
C21 B1 C1 C2 171.6(7) . . . . ?
C6 C1 C2 C3 -0.9(11) . . . . ?
B1 C1 C2 C3 176.6(8) . . . . ?
C6 C1 C2 C13 -179.7(7) . . . . ?
B1 C1 C2 C13 -2.2(11) . . . . ?
C1 C2 C3 C4 0.5(12) . . . . ?
C13 C2 C3 C4 179.4(8) . . . . ?
C2 C3 C4 C5 0.4(13) . . . . ?
C3 C4 C5 C6 -1.0(13) . . . . ?
C4 C5 C6 C1 0.7(12) . . . . ?
C4 C5 C6 C23 179.5(9) . . . . ?
C2 C1 C6 C5 0.2(11) . . . . ?
B1 C1 C6 C5 -177.1(8) . . . . ?
C2 C1 C6 C23 -178.5(8) . . . . ?
B1 C1 C6 C23 4.1(11) . . . . ?
C1 B1 C11 C20 -165.8(8) . . . . ?
C21 B1 C11 C20 13.9(14) . . . . ?
C1 B1 C11 C12 13.8(11) . . . . ?
C21 B1 C11 C12 -166.5(7) . . . . ?
C20 C11 C12 C17 -6.3(12) . . . . ?
B1 C11 C12 C17 174.1(8) . . . . ?
C20 C11 C12 C13 171.4(8) . . . . ?
B1 C11 C12 C13 -8.2(11) . . . . ?
C17 C12 C13 C14 -3.2(11) . . . . ?
C11 C12 C13 C14 179.1(8) . . . . ?
C17 C12 C13 C2 174.7(7) . . . . ?
C11 C12 C13 C2 -3.0(11) . . . . ?
C3 C2 C13 C14 7.6(11) . . . . ?
C1 C2 C13 C14 -173.7(8) . . . . ?
C3 C2 C13 C12 -170.3(8) . . . . ?
C1 C2 C13 C12 8.5(11) . . . . ?
C12 C13 C14 C15 0.0(12) . . . . ?
C2 C13 C14 C15 -177.9(8) . . . . ?
C13 C14 C15 C16 2.5(14) . . . . ?
C14 C15 C16 C17 -1.8(13) . . . . ?
C13 C12 C17 C18 -174.9(7) . . . . ?
C11 C12 C17 C18 2.8(13) . . . . ?
C13 C12 C17 C16 4.0(13) . . . . ?
C11 C12 C17 C16 -178.3(8) . . . . ?
C15 C16 C17 C12 -1.5(13) . . . . ?
C15 C16 C17 C18 177.5(8) . . . . ?
C12 C17 C18 C19 2.7(15) . . . . ?
C16 C17 C18 C19 -176.3(9) . . . . ?
C17 C18 C19 C20 -4.2(15) . . . . ?
C12 C11 C20 C19 4.9(13) . . . . ?
B1 C11 C20 C19 -175.5(10) . . . . ?
C18 C19 C20 C11 0.3(15) . . . . ?
C11 B1 C21 C30 11.4(13) . . . . ?
C1 B1 C21 C30 -168.9(7) . . . . ?
C11 B1 C21 C22 -167.7(8) . . . . ?
C1 B1 C21 C22 12.1(10) . . . . ?
C30 C21 C22 C23 174.4(7) . . . . ?
B1 C21 C22 C23 -6.5(11) . . . . ?
C30 C21 C22 C27 -4.9(11) . . . . ?
B1 C21 C22 C27 174.2(7) . . . . ?
C27 C22 C23 C24 -2.2(12) . . . . ?
C21 C22 C23 C24 178.5(8) . . . . ?
C27 C22 C23 C6 178.4(8) . . . . ?
C21 C22 C23 C6 -0.8(12) . . . . ?
C5 C6 C23 C24 4.2(12) . . . . ?
C1 C6 C23 C24 -177.0(8) . . . . ?
C5 C6 C23 C22 -176.5(8) . . . . ?
C1 C6 C23 C22 2.3(12) . . . . ?
C22 C23 C24 C25 1.9(13) . . . . ?
C6 C23 C24 C25 -178.8(8) . . . . ?
C23 C24 C25 C26 0.1(13) . . . . ?
C24 C25 C26 C27 -1.8(13) . . . . ?
C25 C26 C27 C28 -179.3(8) . . . . ?
C25 C26 C27 C22 1.5(12) . . . . ?
C23 C22 C27 C26 0.6(12) . . . . ?
C21 C22 C27 C26 179.9(8) . . . . ?
C23 C22 C27 C28 -178.7(8) . . . . ?
C21 C22 C27 C28 0.6(11) . . . . ?
C26 C27 C28 C29 -176.3(8) . . . . ?
C22 C27 C28 C29 3.0(12) . . . . ?
C27 C28 C29 C30 -2.1(12) . . . . ?
C22 C21 C30 C29 6.1(11) . . . . ?
B1 C21 C30 C29 -172.9(8) . . . . ?
C28 C29 C30 C21 -2.6(12) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_wa2143
_database_code_depnum_ccdc_archive 'CCDC 1420447'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H20 B N'
_chemical_formula_sum            'C31 H20 B N'
_chemical_formula_weight         417.29

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      cubic
_space_group_IT_number           219
_space_group_name_H-M_alt        'F -4 3 c'
_space_group_name_Hall           'F -4c 2 3'

_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'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y+1/2, x+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, z+1/2, y+1/2'
'-x+1/2, z+1/2, -y+1/2'
'-x+1/2, -z+1/2, y+1/2'
'x+1/2, -z+1/2, -y+1/2'
'z+1/2, y+1/2, x+1/2'
'z+1/2, -y+1/2, -x+1/2'
'-z+1/2, y+1/2, -x+1/2'
'-z+1/2, -y+1/2, x+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x+1/2, y+1/2'
'z, -x+1/2, -y+1/2'
'-z, -x+1/2, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z+1/2, x+1/2'
'-y, z+1/2, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y, -z+1/2, x+1/2'
'y+1/2, x+1, z+1'
'-y+1/2, -x+1, z+1'
'y+1/2, -x+1, -z+1'
'-y+1/2, x+1, -z+1'
'x+1/2, z+1, y+1'
'-x+1/2, z+1, -y+1'
'-x+1/2, -z+1, y+1'
'x+1/2, -z+1, -y+1'
'z+1/2, y+1, x+1'
'z+1/2, -y+1, -x+1'
'-z+1/2, y+1, -x+1'
'-z+1/2, -y+1, x+1'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'z+1/2, x, y+1/2'
'z+1/2, -x, -y+1/2'
'-z+1/2, -x, y+1/2'
'-z+1/2, x, -y+1/2'
'y+1/2, z, x+1/2'
'-y+1/2, z, -x+1/2'
'y+1/2, -z, -x+1/2'
'-y+1/2, -z, x+1/2'
'y+1, x+1/2, z+1'
'-y+1, -x+1/2, z+1'
'y+1, -x+1/2, -z+1'
'-y+1, x+1/2, -z+1'
'x+1, z+1/2, y+1'
'-x+1, z+1/2, -y+1'
'-x+1, -z+1/2, y+1'
'x+1, -z+1/2, -y+1'
'z+1, y+1/2, x+1'
'z+1, -y+1/2, -x+1'
'-z+1, y+1/2, -x+1'
'-z+1, -y+1/2, x+1'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'z+1/2, x+1/2, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x+1/2, y'
'-z+1/2, x+1/2, -y'
'y+1/2, z+1/2, x'
'-y+1/2, z+1/2, -x'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z+1/2, x'
'y+1, x+1, z+1/2'
'-y+1, -x+1, z+1/2'
'y+1, -x+1, -z+1/2'
'-y+1, x+1, -z+1/2'
'x+1, z+1, y+1/2'
'-x+1, z+1, -y+1/2'
'-x+1, -z+1, y+1/2'
'x+1, -z+1, -y+1/2'
'z+1, y+1, x+1/2'
'z+1, -y+1, -x+1/2'
'-z+1, y+1, -x+1/2'
'-z+1, -y+1, x+1/2'

_cell_length_a                   48.2907(17)
_cell_length_b                   48.2907(17)
_cell_length_c                   48.2907(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     112614(12)
_cell_formula_units_Z            192
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    20434
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      25.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             41856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            66865
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_av_R_equivalents  0.1275
_diffrn_reflns_limit_h_min       -58
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       57
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         1.886
_diffrn_reflns_theta_max         25.486
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8695
_reflns_number_gt                5161
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²] 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_abs_structure_details 
; 
 Flack x determined using 1674 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.9(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8695
_refine_ls_number_parameters     595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_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 0.88631(13) 0.50013(13) 0.13939(13) 0.0425(15) Uani 1 1 d . . . . .
C1 C 0.86808(12) 0.51561(10) 0.16214(11) 0.0422(13) Uani 1 1 d . . . . .
C2 C 0.84118(12) 0.52351(11) 0.15451(11) 0.0444(13) Uani 1 1 d . . . . .
C3 C 0.82380(15) 0.53553(13) 0.17417(13) 0.0588(17) Uani 1 1 d . . . . .
H3 H 0.8054 0.5406 0.1693 0.071 Uiso 1 1 calc R U . . .
C4 C 0.83316(16) 0.54004(14) 0.20054(13) 0.0671(19) Uani 1 1 d . . . . .
H4 H 0.8209 0.5472 0.2141 0.081 Uiso 1 1 calc R U . . .
C5 C 0.86010(16) 0.53440(13) 0.20756(12) 0.0623(18) Uani 1 1 d . . . . .
H5 H 0.8665 0.5389 0.2256 0.075 Uiso 1 1 calc R U . . .
C6 C 0.87854(13) 0.52199(12) 0.18837(12) 0.0498(15) Uani 1 1 d . . . . .
C11 C 0.88193(12) 0.51576(11) 0.11012(11) 0.0455(14) Uani 1 1 d . . . . .
C12 C 0.85388(12) 0.52281(10) 0.10385(11) 0.0452(13) Uani 1 1 d . . . . .
C13 C 0.83251(12) 0.52211(11) 0.12498(12) 0.0462(14) Uani 1 1 d . . . . .
C14 C 0.80531(13) 0.52431(13) 0.11664(14) 0.0594(17) Uani 1 1 d . . . . .
H14 H 0.7909 0.5227 0.1300 0.071 Uiso 1 1 calc R U . . .
C15 C 0.79854(14) 0.52886(13) 0.08873(15) 0.0633(18) Uani 1 1 d . . . . .
H15 H 0.7796 0.5291 0.0834 0.076 Uiso 1 1 calc R U . . .
C16 C 0.81815(16) 0.53292(14) 0.06919(15) 0.0667(19) Uani 1 1 d . . . . .
H16 H 0.8130 0.5376 0.0508 0.080 Uiso 1 1 calc R U . . .
C17 C 0.84615(14) 0.53020(11) 0.07645(12) 0.0509(15) Uani 1 1 d . . . . .
C18 C 0.86814(17) 0.53443(13) 0.05693(13) 0.0648(18) Uani 1 1 d . . . . .
H18 H 0.8636 0.5402 0.0387 0.078 Uiso 1 1 calc R U . . .
C19 C 0.89449(15) 0.53062(13) 0.06349(14) 0.0629(17) Uani 1 1 d . . . . .
H19 H 0.9086 0.5348 0.0504 0.075 Uiso 1 1 calc R U . . .
C20 C 0.90173(14) 0.52028(12) 0.09007(13) 0.0559(16) Uani 1 1 d . . . . .
H20 H 0.9206 0.5164 0.0941 0.067 Uiso 1 1 calc R U . . .
C21 C 0.91728(12) 0.49347(11) 0.14998(13) 0.0513(15) Uani 1 1 d . . . . .
C22 C 0.92579(13) 0.50171(12) 0.17724(13) 0.0550(16) Uani 1 1 d . . . . .
C23 C 0.90751(14) 0.51606(13) 0.19565(13) 0.0571(17) Uani 1 1 d . . . . .
C24 C 0.91769(17) 0.52341(15) 0.22174(15) 0.077(2) Uani 1 1 d . . . . .
H24 H 0.9061 0.5335 0.2339 0.092 Uiso 1 1 calc R U . . .
C25 C 0.9442(2) 0.5164(2) 0.2305(2) 0.100(3) Uani 1 1 d . . . . .
H25 H 0.9503 0.5219 0.2484 0.120 Uiso 1 1 calc R U . . .
C26 C 0.96134(19) 0.50212(19) 0.2142(2) 0.089(3) Uani 1 1 d . . . . .
H26 H 0.9791 0.4968 0.2208 0.106 Uiso 1 1 calc R U . . .
C27 C 0.95278(15) 0.49468(15) 0.18646(17) 0.071(2) Uani 1 1 d . . . . .
C28 C 0.97055(15) 0.47952(16) 0.1693(2) 0.083(3) Uani 1 1 d . . . . .
H28 H 0.9885 0.4748 0.1757 0.099 Uiso 1 1 calc R U . . .
C29 C 0.96228(14) 0.47129(14) 0.1433(2) 0.082(3) Uani 1 1 d . . . . .
H29 H 0.9744 0.4610 0.1318 0.099 Uiso 1 1 calc R U . . .
C30 C 0.93543(12) 0.47841(12) 0.13396(16) 0.0619(18) Uani 1 1 d . . . . .
H30 H 0.9298 0.4726 0.1160 0.074 Uiso 1 1 calc R U . . .
N31 N 0.87184(9) 0.46839(9) 0.13542(9) 0.0414(11) Uani 1 1 d . . . . .
C32 C 0.86746(12) 0.45331(11) 0.15826(13) 0.0496(15) Uani 1 1 d . . . . .
H32 H 0.8715 0.4613 0.1758 0.060 Uiso 1 1 calc R U . . .
C33 C 0.85725(13) 0.42667(13) 0.15734(15) 0.0591(17) Uani 1 1 d . . . . .
H33 H 0.8547 0.4164 0.1740 0.071 Uiso 1 1 calc R U . . .
C34 C 0.85080(14) 0.41504(13) 0.13215(16) 0.0648(18) Uani 1 1 d . . . . .
H34 H 0.8433 0.3969 0.1310 0.078 Uiso 1 1 calc R U . . .
C35 C 0.85544(14) 0.43047(13) 0.10853(15) 0.0652(18) Uani 1 1 d . . . . .
H35 H 0.8516 0.4228 0.0908 0.078 Uiso 1 1 calc R U . . .
C36 C 0.86572(13) 0.45699(13) 0.11076(13) 0.0551(16) Uani 1 1 d . . . . .
H36 H 0.8686 0.4675 0.0944 0.066 Uiso 1 1 calc R U . . .
B1A B 0.75411(12) 0.61885(13) 0.13581(14) 0.0430(15) Uani 1 1 d . . . . .
C1A C 0.73930(11) 0.59567(12) 0.11788(12) 0.0475(14) Uani 1 1 d . . . . .
C2A C 0.72867(11) 0.60328(12) 0.09163(13) 0.0537(16) Uani 1 1 d . . . . .
C3A C 0.71821(13) 0.58291(18) 0.07382(16) 0.076(2) Uani 1 1 d . . . . .
H3A H 0.7109 0.5876 0.0561 0.091 Uiso 1 1 calc R U . . .
C4A C 0.71887(16) 0.55526(17) 0.0831(2) 0.091(3) Uani 1 1 d . . . . .
H4A H 0.7131 0.5409 0.0709 0.110 Uiso 1 1 calc R U . . .
C5A C 0.72749(15) 0.54850(16) 0.10911(19) 0.078(2) Uani 1 1 d . . . . .
H5A H 0.7267 0.5297 0.1149 0.094 Uiso 1 1 calc R U . . .
C6A C 0.73720(12) 0.56805(12) 0.12695(15) 0.0558(17) Uani 1 1 d . . . . .
C11A C 0.73694(11) 0.64756(12) 0.13247(12) 0.0474(14) Uani 1 1 d . . . . .
C12A C 0.72668(11) 0.65368(12) 0.10520(13) 0.0497(14) Uani 1 1 d . . . . .
C13A C 0.72612(12) 0.63286(14) 0.08344(13) 0.0551(15) Uani 1 1 d . . . . .
C14A C 0.71955(12) 0.64122(16) 0.05716(15) 0.0656(18) Uani 1 1 d . . . . .
H14A H 0.7200 0.6279 0.0427 0.079 Uiso 1 1 calc R U . . .
C15A C 0.71228(14) 0.6683(2) 0.05064(17) 0.082(2) Uani 1 1 d . . . . .
H15A H 0.7093 0.6736 0.0319 0.098 Uiso 1 1 calc R U . . .
C16A C 0.70937(14) 0.68748(18) 0.07163(16) 0.075(2) Uani 1 1 d . . . . .
H16A H 0.7028 0.7055 0.0675 0.090 Uiso 1 1 calc R U . . .
C17A C 0.71610(13) 0.68052(13) 0.09896(15) 0.0608(18) Uani 1 1 d . . . . .
C18A C 0.71223(14) 0.69956(15) 0.12098(17) 0.0695(19) Uani 1 1 d . . . . .
H18A H 0.7047 0.7173 0.1173 0.083 Uiso 1 1 calc R U . . .
C19A C 0.71930(13) 0.69245(13) 0.14734(16) 0.0645(18) Uani 1 1 d . . . . .
H19A H 0.7156 0.7049 0.1621 0.077 Uiso 1 1 calc R U . . .
C20A C 0.73214(12) 0.66667(12) 0.15289(14) 0.0549(16) Uani 1 1 d . . . . .
H20A H 0.7376 0.6625 0.1713 0.066 Uiso 1 1 calc R U . . .
C21A C 0.76221(12) 0.60815(12) 0.16616(12) 0.0497(15) Uani 1 1 d . . . . .
C22A C 0.75698(12) 0.57993(13) 0.17405(14) 0.0557(16) Uani 1 1 d . . . . .
C23A C 0.74545(13) 0.56041(13) 0.15548(16) 0.0642(18) Uani 1 1 d . . . . .
C24A C 0.74075(15) 0.53321(15) 0.1654(2) 0.085(3) Uani 1 1 d . . . . .
H24A H 0.7325 0.5200 0.1534 0.101 Uiso 1 1 calc R U . . .
C25A C 0.7477(2) 0.5252(2) 0.1920(2) 0.104(4) Uani 1 1 d . . . . .
H25A H 0.7445 0.5066 0.1978 0.125 Uiso 1 1 calc R U . . .
C26A C 0.7590(2) 0.5433(2) 0.2098(2) 0.105(3) Uani 1 1 d . . . . .
H26A H 0.7636 0.5374 0.2279 0.126 Uiso 1 1 calc R U . . .
C27A C 0.76398(14) 0.57107(17) 0.20190(16) 0.070(2) Uani 1 1 d . . . . .
C28A C 0.77487(15) 0.5902(2) 0.22079(16) 0.080(2) Uani 1 1 d . . . . .
H28A H 0.7786 0.5847 0.2393 0.096 Uiso 1 1 calc R U . . .
C29A C 0.78015(13) 0.61662(19) 0.21268(15) 0.077(2) Uani 1 1 d . . . . .
H29A H 0.7879 0.6293 0.2255 0.092 Uiso 1 1 calc R U . . .
C30A C 0.77428(12) 0.62540(15) 0.18554(13) 0.0604(17) Uani 1 1 d . . . . .
H30A H 0.7788 0.6438 0.1804 0.073 Uiso 1 1 calc R U . . .
N31A N 0.78471(8) 0.62388(9) 0.11944(9) 0.0416(10) Uani 1 1 d . . . . .
C32A C 0.79866(11) 0.60208(12) 0.10914(12) 0.0486(14) Uani 1 1 d . . . . .
H32A H 0.7904 0.5843 0.1100 0.058 Uiso 1 1 calc R U . . .
C33A C 0.82442(11) 0.60461(13) 0.09746(14) 0.0557(16) Uani 1 1 d . . . . .
H33A H 0.8337 0.5888 0.0904 0.067 Uiso 1 1 calc R U . . .
C34A C 0.83665(12) 0.63015(13) 0.09598(13) 0.0554(16) Uani 1 1 d . . . . .
H34A H 0.8544 0.6324 0.0877 0.066 Uiso 1 1 calc R U . . .
C35A C 0.82268(13) 0.65223(13) 0.10672(14) 0.0591(17) Uani 1 1 d . . . . .
H35A H 0.8307 0.6702 0.1062 0.071 Uiso 1 1 calc R U . . .
C36A C 0.79701(12) 0.64851(12) 0.11823(13) 0.0507(15) Uani 1 1 d . . . . .
H36A H 0.7876 0.6641 0.1256 0.061 Uiso 1 1 calc R 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
B1 C1 1.594(8) . ?
B1 C21 1.613(9) . ?
B1 C11 1.616(8) . ?
B1 N31 1.695(7) . ?
C1 C6 1.398(8) . ?
C1 C2 1.403(8) . ?
C2 C3 1.394(8) . ?
C2 C13 1.488(8) . ?
C3 C4 1.369(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.418(9) . ?
C5 H5 0.9500 . ?
C6 C23 1.470(9) . ?
C11 C20 1.378(8) . ?
C11 C12 1.429(8) . ?
C12 C17 1.421(8) . ?
C12 C13 1.451(8) . ?
C13 C14 1.378(8) . ?
C14 C15 1.404(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.351(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.434(9) . ?
C18 C19 1.324(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.421(9) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C30 1.377(8) . ?
C21 C22 1.436(9) . ?
C22 C27 1.418(9) . ?
C22 C23 1.432(9) . ?
C23 C24 1.398(9) . ?
C24 C25 1.391(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.333(12) . ?
C25 H25 0.9500 . ?
C26 C27 1.447(11) . ?
C26 H26 0.9500 . ?
C27 C28 1.399(11) . ?
C28 C29 1.376(11) . ?
C28 H28 0.9500 . ?
C29 C30 1.416(9) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
N31 C32 1.338(7) . ?
N31 C36 1.345(7) . ?
C32 C33 1.379(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.376(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(9) . ?
C34 H34 0.9500 . ?
C35 C36 1.378(8) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
B1A C1A 1.586(9) . ?
B1A C21A 1.603(9) . ?
B1A C11A 1.623(8) . ?
B1A N31A 1.693(7) . ?
C1A C6A 1.407(8) . ?
C1A C2A 1.416(8) . ?
C2A C3A 1.401(9) . ?
C2A C13A 1.488(9) . ?
C3A C4A 1.408(11) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.363(11) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.361(9) . ?
C5A H5A 0.9500 . ?
C6A C23A 1.481(9) . ?
C11A C20A 1.370(8) . ?
C11A C12A 1.438(8) . ?
C12A C17A 1.425(8) . ?
C12A C13A 1.455(9) . ?
C13A C14A 1.369(9) . ?
C14A C15A 1.391(10) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.380(11) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.400(9) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.418(10) . ?
C18A C19A 1.362(9) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.417(8) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C21A C30A 1.382(9) . ?
C21A C22A 1.437(8) . ?
C22A C23A 1.415(9) . ?
C22A C27A 1.451(9) . ?
C23A C24A 1.417(9) . ?
C24A C25A 1.384(12) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.339(13) . ?
C25A H25A 0.9500 . ?
C26A C27A 1.414(12) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.400(11) . ?
C28A C29A 1.360(11) . ?
C28A H28A 0.9500 . ?
C29A C30A 1.406(9) . ?
C29A H29A 0.9500 . ?
C30A H30A 0.9500 . ?
N31A C36A 1.331(7) . ?
N31A C32A 1.345(6) . ?
C32A C33A 1.371(8) . ?
C32A H32A 0.9500 . ?
C33A C34A 1.370(8) . ?
C33A H33A 0.9500 . ?
C34A C35A 1.364(8) . ?
C34A H34A 0.9500 . ?
C35A C36A 1.370(8) . ?
C35A H35A 0.9500 . ?
C36A H36A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 B1 C21 112.8(5) . . ?
C1 B1 C11 108.1(4) . . ?
C21 B1 C11 119.4(5) . . ?
C1 B1 N31 105.9(4) . . ?
C21 B1 N31 103.8(4) . . ?
C11 B1 N31 105.6(4) . . ?
C6 C1 C2 120.8(5) . . ?
C6 C1 B1 121.9(5) . . ?
C2 C1 B1 117.2(5) . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 C13 120.2(5) . . ?
C1 C2 C13 120.0(5) . . ?
C4 C3 C2 120.1(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 121.2(6) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.3(5) . . ?
C1 C6 C23 121.2(6) . . ?
C5 C6 C23 121.6(6) . . ?
C20 C11 C12 118.1(5) . . ?
C20 C11 B1 126.7(5) . . ?
C12 C11 B1 114.9(5) . . ?
C17 C12 C11 120.4(5) . . ?
C17 C12 C13 118.3(5) . . ?
C11 C12 C13 121.3(5) . . ?
C14 C13 C12 118.1(5) . . ?
C14 C13 C2 123.0(6) . . ?
C12 C13 C2 118.2(5) . . ?
C13 C14 C15 121.0(6) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 122.0(6) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 119.2(6) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 120.6(6) . . ?
C16 C17 C18 122.4(6) . . ?
C12 C17 C18 116.9(6) . . ?
C19 C18 C17 122.3(6) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 120.1(6) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C11 C20 C19 121.3(6) . . ?
C11 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C30 C21 C22 118.6(6) . . ?
C30 C21 B1 121.2(6) . . ?
C22 C21 B1 120.1(5) . . ?
C27 C22 C23 119.2(6) . . ?
C27 C22 C21 119.0(7) . . ?
C23 C22 C21 121.8(5) . . ?
C24 C23 C22 117.7(6) . . ?
C24 C23 C6 120.0(7) . . ?
C22 C23 C6 122.2(5) . . ?
C25 C24 C23 122.4(9) . . ?
C25 C24 H24 118.8 . . ?
C23 C24 H24 118.8 . . ?
C26 C25 C24 121.2(9) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 119.8(8) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C28 C27 C22 120.2(7) . . ?
C28 C27 C26 120.1(8) . . ?
C22 C27 C26 119.6(8) . . ?
C29 C28 C27 120.8(7) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 119.2(8) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C21 C30 C29 122.1(7) . . ?
C21 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C32 N31 C36 118.2(5) . . ?
C32 N31 B1 117.6(4) . . ?
C36 N31 B1 124.1(5) . . ?
N31 C32 C33 122.5(6) . . ?
N31 C32 H32 118.7 . . ?
C33 C32 H32 118.7 . . ?
C34 C33 C32 119.4(6) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C33 C34 C35 118.3(6) . . ?
C33 C34 H34 120.9 . . ?
C35 C34 H34 120.9 . . ?
C36 C35 C34 119.7(6) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
N31 C36 C35 121.9(6) . . ?
N31 C36 H36 119.0 . . ?
C35 C36 H36 119.0 . . ?
C1A B1A C21A 112.4(5) . . ?
C1A B1A C11A 108.6(5) . . ?
C21A B1A C11A 119.4(5) . . ?
C1A B1A N31A 103.9(4) . . ?
C21A B1A N31A 105.1(4) . . ?
C11A B1A N31A 106.1(4) . . ?
C6A C1A C2A 119.9(6) . . ?
C6A C1A B1A 122.1(5) . . ?
C2A C1A B1A 118.0(5) . . ?
C3A C2A C1A 119.9(6) . . ?
C3A C2A C13A 118.8(6) . . ?
C1A C2A C13A 121.1(5) . . ?
C2A C3A C4A 117.5(7) . . ?
C2A C3A H3A 121.2 . . ?
C4A C3A H3A 121.2 . . ?
C5A C4A C3A 121.8(7) . . ?
C5A C4A H4A 119.1 . . ?
C3A C4A H4A 119.1 . . ?
C6A C5A C4A 121.5(8) . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
C5A C6A C1A 119.0(7) . . ?
C5A C6A C23A 120.6(6) . . ?
C1A C6A C23A 120.4(6) . . ?
C20A C11A C12A 117.5(5) . . ?
C20A C11A B1A 126.1(6) . . ?
C12A C11A B1A 116.3(5) . . ?
C17A C12A C11A 120.3(6) . . ?
C17A C12A C13A 118.0(6) . . ?
C11A C12A C13A 121.7(5) . . ?
C14A C13A C12A 118.1(6) . . ?
C14A C13A C2A 123.3(6) . . ?
C12A C13A C2A 118.1(5) . . ?
C13A C14A C15A 123.1(7) . . ?
C13A C14A H14A 118.5 . . ?
C15A C14A H14A 118.5 . . ?
C16A C15A C14A 119.4(7) . . ?
C16A C15A H15A 120.3 . . ?
C14A C15A H15A 120.3 . . ?
C15A C16A C17A 120.5(7) . . ?
C15A C16A H16A 119.7 . . ?
C17A C16A H16A 119.7 . . ?
C16A C17A C18A 121.4(6) . . ?
C16A C17A C12A 120.1(7) . . ?
C18A C17A C12A 118.6(6) . . ?
C19A C18A C17A 120.3(6) . . ?
C19A C18A H18A 119.8 . . ?
C17A C18A H18A 119.8 . . ?
C18A C19A C20A 120.5(6) . . ?
C18A C19A H19A 119.7 . . ?
C20A C19A H19A 119.7 . . ?
C11A C20A C19A 122.0(6) . . ?
C11A C20A H20A 119.0 . . ?
C19A C20A H20A 119.0 . . ?
C30A C21A C22A 117.8(6) . . ?
C30A C21A B1A 121.9(5) . . ?
C22A C21A B1A 120.3(6) . . ?
C23A C22A C21A 122.2(6) . . ?
C23A C22A C27A 118.8(6) . . ?
C21A C22A C27A 118.9(7) . . ?
C22A C23A C24A 117.8(7) . . ?
C22A C23A C6A 122.0(5) . . ?
C24A C23A C6A 120.2(7) . . ?
C25A C24A C23A 122.3(9) . . ?
C25A C24A H24A 118.8 . . ?
C23A C24A H24A 118.8 . . ?
C26A C25A C24A 120.6(9) . . ?
C26A C25A H25A 119.7 . . ?
C24A C25A H25A 119.7 . . ?
C25A C26A C27A 121.1(9) . . ?
C25A C26A H26A 119.4 . . ?
C27A C26A H26A 119.4 . . ?
C28A C27A C26A 120.9(8) . . ?
C28A C27A C22A 119.8(7) . . ?
C26A C27A C22A 119.3(9) . . ?
C29A C28A C27A 120.1(7) . . ?
C29A C28A H28A 119.9 . . ?
C27A C28A H28A 119.9 . . ?
C28A C29A C30A 120.9(8) . . ?
C28A C29A H29A 119.5 . . ?
C30A C29A H29A 119.5 . . ?
C21A C30A C29A 122.3(7) . . ?
C21A C30A H30A 118.8 . . ?
C29A C30A H30A 118.8 . . ?
C36A N31A C32A 117.4(5) . . ?
C36A N31A B1A 122.6(4) . . ?
C32A N31A B1A 119.8(4) . . ?
N31A C32A C33A 122.4(5) . . ?
N31A C32A H32A 118.8 . . ?
C33A C32A H32A 118.8 . . ?
C34A C33A C32A 119.5(5) . . ?
C34A C33A H33A 120.2 . . ?
C32A C33A H33A 120.2 . . ?
C35A C34A C33A 118.1(5) . . ?
C35A C34A H34A 120.9 . . ?
C33A C34A H34A 120.9 . . ?
C34A C35A C36A 119.9(6) . . ?
C34A C35A H35A 120.0 . . ?
C36A C35A H35A 120.0 . . ?
N31A C36A C35A 122.6(6) . . ?
N31A C36A H36A 118.7 . . ?
C35A C36A H36A 118.7 . . ?

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
C21 B1 C1 C6 -0.9(7) . . . . ?
C11 B1 C1 C6 -135.2(5) . . . . ?
N31 B1 C1 C6 112.0(5) . . . . ?
C21 B1 C1 C2 177.1(5) . . . . ?
C11 B1 C1 C2 42.8(6) . . . . ?
N31 B1 C1 C2 -70.1(6) . . . . ?
C6 C1 C2 C3 -6.1(8) . . . . ?
B1 C1 C2 C3 176.0(5) . . . . ?
C6 C1 C2 C13 166.8(5) . . . . ?
B1 C1 C2 C13 -11.2(7) . . . . ?
C1 C2 C3 C4 1.2(9) . . . . ?
C13 C2 C3 C4 -171.6(6) . . . . ?
C2 C3 C4 C5 3.9(10) . . . . ?
C3 C4 C5 C6 -4.4(10) . . . . ?
C2 C1 C6 C5 5.6(8) . . . . ?
B1 C1 C6 C5 -176.6(5) . . . . ?
C2 C1 C6 C23 -174.4(5) . . . . ?
B1 C1 C6 C23 3.5(8) . . . . ?
C4 C5 C6 C1 -0.4(9) . . . . ?
C4 C5 C6 C23 179.5(6) . . . . ?
C1 B1 C11 C20 142.8(5) . . . . ?
C21 B1 C11 C20 12.1(8) . . . . ?
N31 B1 C11 C20 -104.1(6) . . . . ?
C1 B1 C11 C12 -44.0(6) . . . . ?
C21 B1 C11 C12 -174.8(5) . . . . ?
N31 B1 C11 C12 69.0(5) . . . . ?
C20 C11 C12 C17 9.4(8) . . . . ?
B1 C11 C12 C17 -164.3(5) . . . . ?
C20 C11 C12 C13 -171.8(5) . . . . ?
B1 C11 C12 C13 14.4(7) . . . . ?
C17 C12 C13 C14 10.1(8) . . . . ?
C11 C12 C13 C14 -168.7(5) . . . . ?
C17 C12 C13 C2 -160.5(5) . . . . ?
C11 C12 C13 C2 20.7(8) . . . . ?
C3 C2 C13 C14 -20.1(9) . . . . ?
C1 C2 C13 C14 167.1(6) . . . . ?
C3 C2 C13 C12 150.0(5) . . . . ?
C1 C2 C13 C12 -22.8(8) . . . . ?
C12 C13 C14 C15 -4.0(9) . . . . ?
C2 C13 C14 C15 166.1(6) . . . . ?
C13 C14 C15 C16 -4.0(10) . . . . ?
C14 C15 C16 C17 5.5(10) . . . . ?
C15 C16 C17 C12 1.1(9) . . . . ?
C15 C16 C17 C18 -179.4(6) . . . . ?
C11 C12 C17 C16 170.0(5) . . . . ?
C13 C12 C17 C16 -8.8(8) . . . . ?
C11 C12 C17 C18 -9.6(7) . . . . ?
C13 C12 C17 C18 171.7(5) . . . . ?
C16 C17 C18 C19 -176.8(6) . . . . ?
C12 C17 C18 C19 2.7(9) . . . . ?
C17 C18 C19 C20 4.2(10) . . . . ?
C12 C11 C20 C19 -2.5(8) . . . . ?
B1 C11 C20 C19 170.5(5) . . . . ?
C18 C19 C20 C11 -4.4(9) . . . . ?
C1 B1 C21 C30 175.2(5) . . . . ?
C11 B1 C21 C30 -56.1(7) . . . . ?
N31 B1 C21 C30 61.1(6) . . . . ?
C1 B1 C21 C22 -0.7(7) . . . . ?
C11 B1 C21 C22 128.0(5) . . . . ?
N31 B1 C21 C22 -114.8(5) . . . . ?
C30 C21 C22 C27 1.6(8) . . . . ?
B1 C21 C22 C27 177.6(5) . . . . ?
C30 C21 C22 C23 -176.5(5) . . . . ?
B1 C21 C22 C23 -0.4(8) . . . . ?
C27 C22 C23 C24 2.3(8) . . . . ?
C21 C22 C23 C24 -179.6(5) . . . . ?
C27 C22 C23 C6 -174.9(5) . . . . ?
C21 C22 C23 C6 3.2(8) . . . . ?
C1 C6 C23 C24 178.1(6) . . . . ?
C5 C6 C23 C24 -1.9(9) . . . . ?
C1 C6 C23 C22 -4.8(9) . . . . ?
C5 C6 C23 C22 175.3(6) . . . . ?
C22 C23 C24 C25 -2.3(10) . . . . ?
C6 C23 C24 C25 175.0(6) . . . . ?
C23 C24 C25 C26 -0.3(12) . . . . ?
C24 C25 C26 C27 2.7(13) . . . . ?
C23 C22 C27 C28 177.0(6) . . . . ?
C21 C22 C27 C28 -1.1(9) . . . . ?
C23 C22 C27 C26 0.0(9) . . . . ?
C21 C22 C27 C26 -178.1(6) . . . . ?
C25 C26 C27 C28 -179.5(8) . . . . ?
C25 C26 C27 C22 -2.6(11) . . . . ?
C22 C27 C28 C29 0.3(10) . . . . ?
C26 C27 C28 C29 177.3(6) . . . . ?
C27 C28 C29 C30 0.1(10) . . . . ?
C22 C21 C30 C29 -1.2(8) . . . . ?
B1 C21 C30 C29 -177.2(6) . . . . ?
C28 C29 C30 C21 0.4(10) . . . . ?
C1 B1 N31 C32 -51.8(6) . . . . ?
C21 B1 N31 C32 67.2(6) . . . . ?
C11 B1 N31 C32 -166.4(5) . . . . ?
C1 B1 N31 C36 131.5(5) . . . . ?
C21 B1 N31 C36 -109.6(6) . . . . ?
C11 B1 N31 C36 16.9(7) . . . . ?
C36 N31 C32 C33 0.6(8) . . . . ?
B1 N31 C32 C33 -176.3(5) . . . . ?
N31 C32 C33 C34 -1.1(9) . . . . ?
C32 C33 C34 C35 1.5(10) . . . . ?
C33 C34 C35 C36 -1.4(10) . . . . ?
C32 N31 C36 C35 -0.6(8) . . . . ?
B1 N31 C36 C35 176.2(5) . . . . ?
C34 C35 C36 N31 1.0(10) . . . . ?
C21A B1A C1A C6A -7.8(7) . . . . ?
C11A B1A C1A C6A -142.2(5) . . . . ?
N31A B1A C1A C6A 105.2(6) . . . . ?
C21A B1A C1A C2A 174.0(5) . . . . ?
C11A B1A C1A C2A 39.6(7) . . . . ?
N31A B1A C1A C2A -73.0(6) . . . . ?
C6A C1A C2A C3A -5.4(8) . . . . ?
B1A C1A C2A C3A 172.9(5) . . . . ?
C6A C1A C2A C13A 169.3(5) . . . . ?
B1A C1A C2A C13A -12.4(8) . . . . ?
C1A C2A C3A C4A -0.1(9) . . . . ?
C13A C2A C3A C4A -175.0(6) . . . . ?
C2A C3A C4A C5A 4.5(11) . . . . ?
C3A C4A C5A C6A -3.3(12) . . . . ?
C4A C5A C6A C1A -2.4(10) . . . . ?
C4A C5A C6A C23A 177.6(7) . . . . ?
C2A C1A C6A C5A 6.6(9) . . . . ?
B1A C1A C6A C5A -171.5(6) . . . . ?
C2A C1A C6A C23A -173.4(5) . . . . ?
B1A C1A C6A C23A 8.5(8) . . . . ?
C1A B1A C11A C20A 142.1(6) . . . . ?
C21A B1A C11A C20A 11.5(8) . . . . ?
N31A B1A C11A C20A -106.7(6) . . . . ?
C1A B1A C11A C12A -40.0(6) . . . . ?
C21A B1A C11A C12A -170.6(5) . . . . ?
N31A B1A C11A C12A 71.1(6) . . . . ?
C20A C11A C12A C17A 10.1(8) . . . . ?
B1A C11A C12A C17A -168.0(5) . . . . ?
C20A C11A C12A C13A -168.5(5) . . . . ?
B1A C11A C12A C13A 13.4(8) . . . . ?
C17A C12A C13A C14A 9.9(8) . . . . ?
C11A C12A C13A C14A -171.4(5) . . . . ?
C17A C12A C13A C2A -161.4(5) . . . . ?
C11A C12A C13A C2A 17.3(8) . . . . ?
C3A C2A C13A C14A -14.3(9) . . . . ?
C1A C2A C13A C14A 170.9(5) . . . . ?
C3A C2A C13A C12A 156.5(6) . . . . ?
C1A C2A C13A C12A -18.3(8) . . . . ?
C12A C13A C14A C15A -2.8(9) . . . . ?
C2A C13A C14A C15A 168.0(6) . . . . ?
C13A C14A C15A C16A -5.1(11) . . . . ?
C14A C15A C16A C17A 5.8(11) . . . . ?
C15A C16A C17A C18A -177.5(7) . . . . ?
C15A C16A C17A C12A 1.5(10) . . . . ?
C11A C12A C17A C16A 172.0(6) . . . . ?
C13A C12A C17A C16A -9.3(9) . . . . ?
C11A C12A C17A C18A -9.0(9) . . . . ?
C13A C12A C17A C18A 169.7(6) . . . . ?
C16A C17A C18A C19A -179.1(7) . . . . ?
C12A C17A C18A C19A 1.9(10) . . . . ?
C17A C18A C19A C20A 3.9(10) . . . . ?
C12A C11A C20A C19A -4.3(8) . . . . ?
B1A C11A C20A C19A 173.5(5) . . . . ?
C18A C19A C20A C11A -2.6(10) . . . . ?
C1A B1A C21A C30A -177.3(5) . . . . ?
C11A B1A C21A C30A -48.4(7) . . . . ?
N31A B1A C21A C30A 70.4(6) . . . . ?
C1A B1A C21A C22A 2.6(7) . . . . ?
C11A B1A C21A C22A 131.5(5) . . . . ?
N31A B1A C21A C22A -109.8(5) . . . . ?
C30A C21A C22A C23A -178.1(5) . . . . ?
B1A C21A C22A C23A 2.0(8) . . . . ?
C30A C21A C22A C27A 1.3(8) . . . . ?
B1A C21A C22A C27A -178.6(5) . . . . ?
C21A C22A C23A C24A -179.1(6) . . . . ?
C27A C22A C23A C24A 1.5(8) . . . . ?
C21A C22A C23A C6A -2.0(9) . . . . ?
C27A C22A C23A C6A 178.6(5) . . . . ?
C5A C6A C23A C22A 176.6(6) . . . . ?
C1A C6A C23A C22A -3.4(9) . . . . ?
C5A C6A C23A C24A -6.3(9) . . . . ?
C1A C6A C23A C24A 173.7(6) . . . . ?
C22A C23A C24A C25A -1.9(10) . . . . ?
C6A C23A C24A C25A -179.1(7) . . . . ?
C23A C24A C25A C26A 1.1(13) . . . . ?
C24A C25A C26A C27A 0.1(14) . . . . ?
C25A C26A C27A C28A 177.8(8) . . . . ?
C25A C26A C27A C22A -0.4(12) . . . . ?
C23A C22A C27A C28A -178.7(6) . . . . ?
C21A C22A C27A C28A 1.9(9) . . . . ?
C23A C22A C27A C26A -0.4(9) . . . . ?
C21A C22A C27A C26A -179.8(6) . . . . ?
C26A C27A C28A C29A 178.5(7) . . . . ?
C22A C27A C28A C29A -3.3(10) . . . . ?
C27A C28A C29A C30A 1.4(10) . . . . ?
C22A C21A C30A C29A -3.2(9) . . . . ?
B1A C21A C30A C29A 176.6(5) . . . . ?
C28A C29A C30A C21A 2.0(10) . . . . ?
C1A B1A N31A C36A 146.1(5) . . . . ?
C21A B1A N31A C36A -95.6(6) . . . . ?
C11A B1A N31A C36A 31.8(7) . . . . ?
C1A B1A N31A C32A -39.7(6) . . . . ?
C21A B1A N31A C32A 78.6(6) . . . . ?
C11A B1A N31A C32A -154.1(5) . . . . ?
C36A N31A C32A C33A -0.7(8) . . . . ?
B1A N31A C32A C33A -175.2(5) . . . . ?
N31A C32A C33A C34A -0.2(10) . . . . ?
C32A C33A C34A C35A 1.0(10) . . . . ?
C33A C34A C35A C36A -0.8(10) . . . . ?
C32A N31A C36A C35A 0.9(9) . . . . ?
B1A N31A C36A C35A 175.2(6) . . . . ?
C34A C35A C36A N31A -0.1(10) . . . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.032

# SQUEEZE RESULTS 
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.000 -0.000 774 63 ' '
2 0.500 -0.000 -0.000 773 63 ' '
3 -0.000 -0.000 0.500 773 63 ' '
4 0.500 -0.000 0.500 774 63 ' '
5 0.904 0.096 0.096 43 7 ' '
6 0.404 0.095 0.096 42 7 ' '
7 0.096 0.096 0.404 43 7 ' '
8 0.596 0.096 0.404 43 7 ' '
9 0.404 0.096 0.596 43 7 ' '
10 0.904 0.095 0.596 42 7 ' '
11 0.596 0.096 0.904 43 7 ' '
12 0.096 0.096 0.904 43 7 ' '
13 0.157 0.157 0.157 41 11 ' '
14 0.657 0.157 0.157 41 11 ' '
15 0.843 0.157 0.343 41 11 ' '
16 0.343 0.157 0.343 41 11 ' '
17 0.657 0.157 0.657 41 11 ' '
18 0.157 0.157 0.657 41 11 ' '
19 0.343 0.157 0.843 41 11 ' '
20 0.843 0.157 0.843 41 11 ' '
21 0.250 0.250 0.250 579 47 ' '
22 0.750 0.250 0.250 579 47 ' '
23 0.250 0.250 0.750 579 47 ' '
24 0.750 0.250 0.750 579 47 ' '
25 0.343 0.343 0.157 41 11 ' '
26 0.843 0.343 0.157 41 11 ' '
27 0.657 0.343 0.343 41 11 ' '
28 0.157 0.343 0.343 41 11 ' '
29 0.843 0.343 0.657 41 11 ' '
30 0.343 0.343 0.657 41 11 ' '
31 0.157 0.343 0.843 41 11 ' '
32 0.657 0.343 0.843 41 11 ' '
33 0.596 0.404 0.096 43 7 ' '
34 0.096 0.404 0.096 43 7 ' '
35 0.904 0.404 0.404 43 7 ' '
36 0.404 0.404 0.404 42 7 ' '
37 0.096 0.404 0.596 43 7 ' '
38 0.596 0.404 0.596 43 7 ' '
39 0.404 0.404 0.904 43 7 ' '
40 0.904 0.404 0.904 42 7 ' '
41 -0.000 0.500 -0.000 773 63 ' '
42 0.500 0.500 -0.000 774 63 ' '
43 1.000 0.500 0.500 774 63 ' '
44 0.500 0.500 0.500 773 63 ' '
45 0.404 0.596 0.096 43 7 ' '
46 0.904 0.596 0.096 42 7 ' '
47 0.596 0.596 0.404 43 7 ' '
48 0.096 0.596 0.404 43 7 ' '
49 0.904 0.596 0.596 43 7 ' '
50 0.404 0.596 0.596 42 7 ' '
51 0.096 0.596 0.904 43 7 ' '
52 0.596 0.596 0.904 43 7 ' '
53 0.657 0.657 0.157 41 11 ' '
54 0.157 0.657 0.157 41 11 ' '
55 0.343 0.657 0.343 41 11 ' '
56 0.843 0.657 0.343 41 11 ' '
57 0.157 0.657 0.657 41 11 ' '
58 0.657 0.657 0.657 41 11 ' '
59 0.843 0.657 0.843 41 11 ' '
60 0.343 0.657 0.843 41 11 ' '
61 0.250 0.750 0.250 579 47 ' '
62 0.750 0.750 0.250 579 47 ' '
63 0.250 0.750 0.750 579 47 ' '
64 0.750 0.750 0.750 579 47 ' '
65 0.843 0.843 0.157 41 11 ' '
66 0.343 0.843 0.157 41 11 ' '
67 0.157 0.843 0.343 41 11 ' '
68 0.657 0.843 0.343 41 11 ' '
69 0.343 0.843 0.657 41 11 ' '
70 0.843 0.843 0.657 41 11 ' '
71 0.657 0.843 0.843 41 11 ' '
72 0.157 0.843 0.843 41 11 ' '
73 0.096 0.904 0.096 43 7 ' '
74 0.596 0.904 0.096 43 7 ' '
75 0.404 0.904 0.404 43 7 ' '
76 0.904 0.904 0.404 42 7 ' '
77 0.596 0.904 0.596 43 7 ' '
78 0.096 0.904 0.596 43 7 ' '
79 0.904 0.904 0.904 43 7 ' '
80 0.404 0.904 0.904 42 7 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2014/6


