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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8Cl
_database_code_depnum_ccdc_archive 'CCDC 1819488'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            8Cl
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 B Cl N'
_chemical_formula_sum            'C18 H13 B Cl N'
_chemical_formula_weight         289.55

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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.4311(11)
_cell_length_b                   7.5161(6)
_cell_length_c                   17.3831(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.691(3)
_cell_angle_gamma                90
_cell_volume                     1462.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4344
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      23.02

_exptl_crystal_description       blocklike
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.121
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33647
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.393
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3229
_reflns_number_gt                2018
_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 (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)+(0.0440P)²+0.2732P] 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         3229
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Cl1 Cl 1.02030(5) 0.32275(7) 0.13200(3) 0.03520(18) Uani 1 1 d . . . . .
N1 N 1.01724(14) 0.5283(2) 0.26244(9) 0.0223(4) Uani 1 1 d . . . . .
B1 B 0.9763(2) 0.5117(3) 0.18105(14) 0.0242(5) Uani 1 1 d . . . . .
C13 C 0.86157(17) 0.7985(2) 0.17970(11) 0.0238(5) Uani 1 1 d . . . . .
C11 C 0.97243(17) 0.6635(2) 0.30566(11) 0.0232(4) Uani 1 1 d . . . . .
C14 C 0.89843(17) 0.6577(2) 0.13645(11) 0.0228(5) Uani 1 1 d . . . . .
C12 C 0.89301(17) 0.7930(2) 0.26616(11) 0.0236(5) Uani 1 1 d . . . . .
C1 C 1.00404(18) 0.6654(3) 0.38769(11) 0.0275(5) Uani 1 1 d . . . . .
H1 H 1.0590 0.5797 0.4140 0.033 Uiso 1 1 calc R U . . .
C4 C 0.84514(18) 0.9149(3) 0.31241(12) 0.0304(5) Uani 1 1 d . . . . .
H4 H 0.7894 1.0009 0.2872 0.036 Uiso 1 1 calc R U . . .
C3 C 0.87619(19) 0.9141(3) 0.39312(13) 0.0355(6) Uani 1 1 d . . . . .
H3 H 0.8424 0.9988 0.4228 0.043 Uiso 1 1 calc R U . . .
C2 C 0.95672(19) 0.7895(3) 0.43072(12) 0.0331(5) Uani 1 1 d . . . . .
H2 H 0.9794 0.7897 0.4864 0.040 Uiso 1 1 calc R U . . .
C6 C 0.7724(2) 0.9431(3) 0.05772(13) 0.0403(6) Uani 1 1 d . . . . .
H6 H 0.7300 1.0411 0.0309 0.048 Uiso 1 1 calc R U . . .
C8 C 0.86942(18) 0.6643(3) 0.05404(11) 0.0290(5) Uani 1 1 d . . . . .
H8 H 0.8935 0.5694 0.0246 0.035 Uiso 1 1 calc R U . . .
C7 C 0.80726(19) 0.8043(3) 0.01502(13) 0.0358(5) Uani 1 1 d . . . . .
H7 H 0.7883 0.8062 -0.0408 0.043 Uiso 1 1 calc R U . . .
C5 C 0.79819(19) 0.9407(3) 0.13831(13) 0.0338(5) Uani 1 1 d . . . . .
H5 H 0.7728 1.0367 0.1665 0.041 Uiso 1 1 calc R U . . .
C15 C 1.11097(18) 0.4153(2) 0.30558(11) 0.0245(5) Uani 1 1 d . . . . .
C19 C 1.1748(2) 0.1529(3) 0.37908(13) 0.0416(6) Uani 1 1 d . . . . .
H19 H 1.1570 0.0425 0.4008 0.050 Uiso 1 1 calc R U . . .
C17 C 1.3180(2) 0.3685(3) 0.35804(12) 0.0356(6) Uani 1 1 d . . . . .
H17 H 1.3986 0.4073 0.3655 0.043 Uiso 1 1 calc R U . . .
C20 C 1.0831(2) 0.2556(3) 0.33658(12) 0.0345(5) Uani 1 1 d . . . . .
H20 H 1.0025 0.2166 0.3290 0.041 Uiso 1 1 calc R U . . .
C18 C 1.2914(2) 0.2100(3) 0.38995(13) 0.0406(6) Uani 1 1 d . . . . .
H18 H 1.3536 0.1396 0.4196 0.049 Uiso 1 1 calc R U . . .
C16 C 1.22767(18) 0.4715(3) 0.31520(11) 0.0273(5) Uani 1 1 d . . . . .
H16 H 1.2460 0.5804 0.2925 0.033 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
Cl1 B1 1.781(2) . ?
N1 B1 1.403(3) . ?
N1 C11 1.420(2) . ?
N1 C15 1.451(2) . ?
B1 C14 1.523(3) . ?
C13 C5 1.405(3) . ?
C13 C14 1.411(3) . ?
C13 C12 1.473(3) . ?
C11 C1 1.398(3) . ?
C11 C12 1.411(3) . ?
C14 C8 1.404(3) . ?
C12 C4 1.401(3) . ?
C1 C2 1.373(3) . ?
C4 C3 1.376(3) . ?
C3 C2 1.381(3) . ?
C6 C5 1.372(3) . ?
C6 C7 1.385(3) . ?
C8 C7 1.370(3) . ?
C15 C16 1.377(3) . ?
C15 C20 1.379(3) . ?
C19 C18 1.376(3) . ?
C19 C20 1.388(3) . ?
C17 C18 1.374(3) . ?
C17 C16 1.382(3) . ?

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
B1 N1 C11 121.00(16) . . ?
B1 N1 C15 121.97(16) . . ?
C11 N1 C15 116.96(15) . . ?
N1 B1 C14 119.38(18) . . ?
N1 B1 Cl1 119.02(16) . . ?
C14 B1 Cl1 121.58(16) . . ?
C5 C13 C14 118.44(18) . . ?
C5 C13 C12 122.53(18) . . ?
C14 C13 C12 119.01(17) . . ?
C1 C11 C12 119.82(18) . . ?
C1 C11 N1 120.03(17) . . ?
C12 C11 N1 120.12(17) . . ?
C8 C14 C13 118.88(18) . . ?
C8 C14 B1 122.52(18) . . ?
C13 C14 B1 118.43(17) . . ?
C4 C12 C11 117.35(18) . . ?
C4 C12 C13 121.59(18) . . ?
C11 C12 C13 121.06(17) . . ?
C2 C1 C11 120.88(19) . . ?
C3 C4 C12 122.1(2) . . ?
C4 C3 C2 119.67(19) . . ?
C1 C2 C3 120.1(2) . . ?
C5 C6 C7 120.8(2) . . ?
C7 C8 C14 121.6(2) . . ?
C8 C7 C6 119.3(2) . . ?
C6 C5 C13 121.0(2) . . ?
C16 C15 C20 120.97(19) . . ?
C16 C15 N1 118.61(17) . . ?
C20 C15 N1 120.42(19) . . ?
C18 C19 C20 120.4(2) . . ?
C18 C17 C16 120.1(2) . . ?
C15 C20 C19 118.8(2) . . ?
C17 C18 C19 120.2(2) . . ?
C15 C16 C17 119.56(19) . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_9Ph
_database_code_depnum_ccdc_archive 'CCDC 1819489'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            9Ph
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 B N3'
_chemical_formula_sum            'C24 H18 B N3'
_chemical_formula_weight         359.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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                   8.3238(12)
_cell_length_b                   9.5871(14)
_cell_length_c                   11.8893(15)
_cell_angle_alpha                83.315(4)
_cell_angle_beta                 81.252(4)
_cell_angle_gamma                76.743(5)
_cell_volume                     909.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      27.90

_exptl_crystal_description       needlelike
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32806
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.190
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4024
_reflns_number_gt                2891
_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 (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)+(0.0961P)²+0.4838P] 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         4024
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2044
_refine_ls_wR_factor_gt          0.1861
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_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
N3 N 0.8830(2) 0.7725(2) 0.69739(16) 0.0255(4) Uani 1 1 d . . . . .
N2 N 0.8838(2) 0.7905(2) 0.79941(16) 0.0261(4) Uani 1 1 d . . . . .
N1 N 0.9827(2) 0.89132(19) 0.80786(15) 0.0240(4) Uani 1 1 d . . . . .
C24 C 0.5766(3) 0.5003(3) 0.6455(2) 0.0381(6) Uani 1 1 d . . . . .
H24 H 0.5115 0.4350 0.6340 0.046 Uiso 1 1 calc R U . . .
C23 C 0.7124(3) 0.5179(3) 0.5677(2) 0.0351(6) Uani 1 1 d . . . . .
H23 H 0.7395 0.4666 0.5012 0.042 Uiso 1 1 calc R U . . .
C22 C 0.8096(3) 0.6106(2) 0.5864(2) 0.0295(5) Uani 1 1 d . . . . .
H22 H 0.9018 0.6246 0.5319 0.035 Uiso 1 1 calc R U . . .
C16 C 0.7727(3) 0.6824(2) 0.68411(19) 0.0251(5) Uani 1 1 d . . . . .
B1 B 0.9529(3) 1.0321(3) 0.7503(2) 0.0232(5) Uani 1 1 d . . . . .
C14 C 1.0580(3) 1.1326(2) 0.78095(18) 0.0242(5) Uani 1 1 d . . . . .
C8 C 1.0391(3) 1.2757(2) 0.7331(2) 0.0287(5) Uani 1 1 d . . . . .
H8 H 0.9644 1.3092 0.6779 0.034 Uiso 1 1 calc R U . . .
C7 C 1.1257(3) 1.3690(3) 0.7637(2) 0.0313(5) Uani 1 1 d . . . . .
H7 H 1.1118 1.4650 0.7295 0.038 Uiso 1 1 calc R U . . .
C6 C 1.2336(3) 1.3205(3) 0.8454(2) 0.0326(6) Uani 1 1 d . . . . .
H6 H 1.2938 1.3840 0.8670 0.039 Uiso 1 1 calc R U . . .
C19 C 0.5788(3) 1.1579(2) 0.5123(2) 0.0313(6) Uani 1 1 d . . . . .
H19 H 0.4997 1.1817 0.4596 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7421(3) 1.1681(2) 0.4773(2) 0.0295(5) Uani 1 1 d . . . . .
H18 H 0.7750 1.2003 0.4004 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8588(3) 1.1316(2) 0.55408(19) 0.0265(5) Uani 1 1 d . . . . .
H17 H 0.9699 1.1414 0.5289 0.032 Uiso 1 1 calc R U . . .
C15 C 0.8165(3) 1.0811(2) 0.66691(19) 0.0239(5) Uani 1 1 d . . . . .
C25 C 0.5354(3) 0.5781(3) 0.7407(2) 0.0386(6) Uani 1 1 d . . . . .
H25 H 0.4388 0.5688 0.7925 0.046 Uiso 1 1 calc R U . . .
C26 C 0.6326(3) 0.6692(3) 0.7615(2) 0.0310(5) Uani 1 1 d . . . . .
H26 H 0.6043 0.7217 0.8273 0.037 Uiso 1 1 calc R U . . .
C11 C 1.0963(3) 0.8416(2) 0.88881(18) 0.0230(5) Uani 1 1 d . . . . .
C1 C 1.1177(3) 0.7004(2) 0.9389(2) 0.0277(5) Uani 1 1 d . . . . .
H1 H 1.0556 0.6376 0.9187 0.033 Uiso 1 1 calc R U . . .
C2 C 1.2289(3) 0.6515(3) 1.0176(2) 0.0308(5) Uani 1 1 d . . . . .
H2 H 1.2417 0.5558 1.0522 0.037 Uiso 1 1 calc R U . . .
C3 C 1.3216(3) 0.7421(3) 1.0461(2) 0.0326(6) Uani 1 1 d . . . . .
H3 H 1.3978 0.7089 1.1003 0.039 Uiso 1 1 calc R U . . .
C4 C 1.3027(3) 0.8806(3) 0.9954(2) 0.0298(5) Uani 1 1 d . . . . .
H4 H 1.3685 0.9411 1.0147 0.036 Uiso 1 1 calc R U . . .
C12 C 1.1895(3) 0.9357(2) 0.91617(18) 0.0236(5) Uani 1 1 d . . . . .
C13 C 1.1695(3) 1.0843(2) 0.86346(19) 0.0243(5) Uani 1 1 d . . . . .
C5 C 1.2545(3) 1.1817(3) 0.8954(2) 0.0291(5) Uani 1 1 d . . . . .
H5 H 1.3271 1.1512 0.9521 0.035 Uiso 1 1 calc R U . . .
C21 C 0.6491(3) 1.0736(2) 0.7008(2) 0.0274(5) Uani 1 1 d . . . . .
H21 H 0.6155 1.0410 0.7774 0.033 Uiso 1 1 calc R U . . .
C20 C 0.5317(3) 1.1126(3) 0.6248(2) 0.0301(5) Uani 1 1 d . . . . .
H20 H 0.4189 1.1083 0.6502 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
N3 N2 1.246(3) . ?
N3 C16 1.434(3) . ?
N2 N1 1.427(3) . ?
N1 C11 1.418(3) . ?
N1 B1 1.426(3) . ?
C24 C23 1.377(4) . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C23 C22 1.388(3) . ?
C23 H23 0.9500 . ?
C22 C16 1.377(3) . ?
C22 H22 0.9500 . ?
C16 C26 1.391(3) . ?
B1 C14 1.546(3) . ?
B1 C15 1.575(3) . ?
C14 C8 1.406(3) . ?
C14 C13 1.419(3) . ?
C8 C7 1.380(3) . ?
C8 H8 0.9500 . ?
C7 C6 1.391(3) . ?
C7 H7 0.9500 . ?
C6 C5 1.377(3) . ?
C6 H6 0.9500 . ?
C19 C18 1.382(3) . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C18 C17 1.392(3) . ?
C18 H18 0.9500 . ?
C17 C15 1.393(3) . ?
C17 H17 0.9500 . ?
C15 C21 1.406(3) . ?
C25 C26 1.384(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C11 C1 1.397(3) . ?
C11 C12 1.410(3) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C12 1.408(3) . ?
C4 H4 0.9500 . ?
C12 C13 1.472(3) . ?
C13 C5 1.407(3) . ?
C5 H5 0.9500 . ?
C21 C20 1.391(3) . ?
C21 H21 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
N2 N3 C16 112.33(18) . . ?
N3 N2 N1 110.35(17) . . ?
C11 N1 B1 125.09(19) . . ?
C11 N1 N2 112.44(17) . . ?
B1 N1 N2 122.05(17) . . ?
C23 C24 C25 119.7(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C16 C22 C23 120.0(2) . . ?
C16 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C16 C26 120.5(2) . . ?
C22 C16 N3 115.9(2) . . ?
C26 C16 N3 123.5(2) . . ?
N1 B1 C14 114.80(19) . . ?
N1 B1 C15 121.6(2) . . ?
C14 B1 C15 123.50(19) . . ?
C8 C14 C13 118.3(2) . . ?
C8 C14 B1 121.2(2) . . ?
C13 C14 B1 120.3(2) . . ?
C7 C8 C14 122.0(2) . . ?
C7 C8 H8 119.0 . . ?
C14 C8 H8 119.0 . . ?
C8 C7 C6 119.0(2) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C17 C15 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C15 C17 H17 119.2 . . ?
C17 C15 C21 116.9(2) . . ?
C17 C15 B1 120.7(2) . . ?
C21 C15 B1 122.4(2) . . ?
C26 C25 C24 121.0(2) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C16 118.7(2) . . ?
C25 C26 H26 120.7 . . ?
C16 C26 H26 120.7 . . ?
C1 C11 C12 120.6(2) . . ?
C1 C11 N1 120.3(2) . . ?
C12 C11 N1 119.05(19) . . ?
C2 C1 C11 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C11 C1 H1 119.8 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C12 122.3(2) . . ?
C3 C4 H4 118.8 . . ?
C12 C4 H4 118.8 . . ?
C4 C12 C11 116.9(2) . . ?
C4 C12 C13 121.8(2) . . ?
C11 C12 C13 121.29(19) . . ?
C5 C13 C14 118.9(2) . . ?
C5 C13 C12 121.7(2) . . ?
C14 C13 C12 119.4(2) . . ?
C6 C5 C13 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C13 C5 H5 119.6 . . ?
C20 C21 C15 121.6(2) . . ?
C20 C21 H21 119.2 . . ?
C15 C21 H21 119.2 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?

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
C16 N3 N2 N1 -174.53(16) . . . . ?
N3 N2 N1 C11 -131.80(19) . . . . ?
N3 N2 N1 B1 55.3(3) . . . . ?
C25 C24 C23 C22 1.7(4) . . . . ?
C24 C23 C22 C16 1.5(3) . . . . ?
C23 C22 C16 C26 -3.7(3) . . . . ?
C23 C22 C16 N3 178.28(19) . . . . ?
N2 N3 C16 C22 -155.01(19) . . . . ?
N2 N3 C16 C26 27.0(3) . . . . ?
C11 N1 B1 C14 0.9(3) . . . . ?
N2 N1 B1 C14 172.85(18) . . . . ?
C11 N1 B1 C15 -176.33(19) . . . . ?
N2 N1 B1 C15 -4.4(3) . . . . ?
N1 B1 C14 C8 -178.4(2) . . . . ?
C15 B1 C14 C8 -1.3(3) . . . . ?
N1 B1 C14 C13 -2.0(3) . . . . ?
C15 B1 C14 C13 175.1(2) . . . . ?
C13 C14 C8 C7 0.2(3) . . . . ?
B1 C14 C8 C7 176.7(2) . . . . ?
C14 C8 C7 C6 -0.7(4) . . . . ?
C8 C7 C6 C5 0.0(4) . . . . ?
C20 C19 C18 C17 0.8(3) . . . . ?
C19 C18 C17 C15 1.4(3) . . . . ?
C18 C17 C15 C21 -2.2(3) . . . . ?
C18 C17 C15 B1 176.5(2) . . . . ?
N1 B1 C15 C17 -123.3(2) . . . . ?
C14 B1 C15 C17 59.7(3) . . . . ?
N1 B1 C15 C21 55.4(3) . . . . ?
C14 B1 C15 C21 -121.6(2) . . . . ?
C23 C24 C25 C26 -2.7(4) . . . . ?
C24 C25 C26 C16 0.6(4) . . . . ?
C22 C16 C26 C25 2.6(3) . . . . ?
N3 C16 C26 C25 -179.5(2) . . . . ?
B1 N1 C11 C1 -179.0(2) . . . . ?
N2 N1 C11 C1 8.4(3) . . . . ?
B1 N1 C11 C12 -0.3(3) . . . . ?
N2 N1 C11 C12 -172.93(18) . . . . ?
C12 C11 C1 C2 1.1(3) . . . . ?
N1 C11 C1 C2 179.8(2) . . . . ?
C11 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C12 1.1(4) . . . . ?
C3 C4 C12 C11 -0.9(3) . . . . ?
C3 C4 C12 C13 179.4(2) . . . . ?
C1 C11 C12 C4 -0.2(3) . . . . ?
N1 C11 C12 C4 -178.88(19) . . . . ?
C1 C11 C12 C13 179.45(19) . . . . ?
N1 C11 C12 C13 0.7(3) . . . . ?
C8 C14 C13 C5 1.0(3) . . . . ?
B1 C14 C13 C5 -175.5(2) . . . . ?
C8 C14 C13 C12 179.03(19) . . . . ?
B1 C14 C13 C12 2.5(3) . . . . ?
C4 C12 C13 C5 -4.3(3) . . . . ?
C11 C12 C13 C5 176.1(2) . . . . ?
C4 C12 C13 C14 177.7(2) . . . . ?
C11 C12 C13 C14 -1.9(3) . . . . ?
C7 C6 C5 C13 1.2(4) . . . . ?
C14 C13 C5 C6 -1.7(3) . . . . ?
C12 C13 C5 C6 -179.7(2) . . . . ?
C17 C15 C21 C20 1.0(3) . . . . ?
B1 C15 C21 C20 -177.7(2) . . . . ?
C18 C19 C20 C21 -2.0(3) . . . . ?
C15 C21 C20 C19 1.2(3) . . . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-4

_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_8Ph
_database_code_depnum_ccdc_archive 'CCDC 1819492'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;

_vrf_DIFMN02_ALERT_2_B           
;
PROBLEM:  The minimum difference density is < -0.1*ZMAX*1.00
            _refine_diff_density_min given =     -0.875
            Test value =     -0.700
         
RESPONSE: This error is a result of the identical substitution of the boron and nitrogen atoms in the central ring.
;

_vrf_RINTA01_ALERT_3_B           
;
PROBLEM:  The value of Rint is greater than 0.18
            Rint given   0.233   

RESPONSE: This error is a result of the data obtained for the structure.  
;

_vrf_PLAT020_ALERT_3_B           
;
PROBLEM:   The Value of Rint is Greater Than 0.12 .........      0.233 Report 
         
RESPONSE: This error is a result of the data obtained for the structure.  
;

_vrf_PLAT097_ALERT_2_B           
;
PROBLEM:  Large Reported Max.  (Positive) Residual Density       1.28 eA-3    

RESPONSE: The large reported density is a result of using EADP restraints to model the positional disorder, without the restraint this error is not present.  
;

_vrf_PLAT098_ALERT_2_B           
;
PROBLEM:  Large Reported Min.  (Negative) Residual Density      -0.88 eA-3  
         
RESPONSE: The large reported density is a result of using EADP restraints to model the positional disorder, without the restraint this error is not present.  
;

_vrf_DIFMN03_ALERT_1_C           
;
PROBLEM:  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.  

RESPONSE: This error is a result of the identical substitution of the boron and nitrogen atoms in the central ring. 
;

_vrf_DIFMX02_ALERT_1_C           
;
PROBLEM:  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
         
RESPONSE: This error is a result of the identical substitution of the boron and nitrogen atoms in the central ring.
;

_vrf_PLAT340_ALERT_3_C           
;
PROBLEM:  Low Bond Precision on  C-C Bonds ...............     0.0066 Ang.   

RESPONSE: This error is a result of the data obtained for the structure.    
;

_vrf_PLAT083_ALERT_2_G           
;
PROBLEM:  SHELXL Second Parameter in WGHT  Unusually Large      27.93 Why ?  
         
RESPONSE: The large WGHT parameter is a result of the positional disorder of the boron and nitrogen atoms.
;

_vrf_PLAT171_ALERT_4_G           
;
PROBLEM:  The CIF-Embedded .res File Contains EADP Records          1 Report 

RESPONSE: The EADP restraint was used to model the structure to fit better anistropic parameters of the boron and nitrogen atoms.  
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            8Ph
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 B N'
_chemical_formula_sum            'C24 H18 B N'
_chemical_formula_weight         331.20

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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   26.7935(17)
_cell_length_b                   26.7935(17)
_cell_length_c                   9.9207(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7122.0(13)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7739
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      25.03

_exptl_crystal_description       Needlelike
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             2784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.152
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61789
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_av_R_equivalents  0.2326
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.665
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3372
_reflns_number_gt                1912
_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
'Positional disorder of the boron and nitrogen atoms.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+27.9282P] 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         3372
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_ref         0.2014
_refine_ls_wR_factor_gt          0.1689
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
N1 N 1.01646(13) 0.02381(14) 0.2382(3) 0.0516(10) Uani 1 1 d . . . . .
C1 C 1.07034(17) -0.15924(16) 0.2313(4) 0.0492(12) Uani 1 1 d . . . . .
H1 H 1.0879 -0.1899 0.2251 0.059 Uiso 1 1 calc R U . . .
C1A C 1.07034(13) 0.02438(14) 0.2044(3) 0.0299(9) Uani 1 1 d . . . . .
C2 C 1.09525(16) -0.11504(15) 0.2132(4) 0.0407(10) Uani 1 1 d . . . . .
H14 H 1.1302 -0.1156 0.1964 0.049 Uiso 1 1 calc R U . . .
C3 C 1.07021(14) -0.06892(14) 0.2190(3) 0.0317(9) Uani 1 1 d . . . . .
C4 C 1.09599(13) -0.02122(14) 0.1954(3) 0.0295(9) Uani 1 1 d . . . . .
C5 C 0.98895(14) 0.07395(15) 0.2458(4) 0.0355(10) Uani 1 1 d . . . . .
C6 C 0.9759(2) 0.09466(16) 0.3676(4) 0.0600(14) Uani 1 1 d . . . . .
H17 H 0.9835 0.0772 0.4484 0.072 Uiso 1 1 calc R U . . .
C7 C 0.9519(2) 0.14045(17) 0.3757(5) 0.0650(14) Uani 1 1 d . . . . .
H18 H 0.9429 0.1538 0.4609 0.078 Uiso 1 1 calc R U . . .
C8 C 0.94132(17) 0.16628(19) 0.2599(5) 0.0563(13) Uani 1 1 d . . . . .
H2 H 0.9252 0.1978 0.2650 0.068 Uiso 1 1 calc R U . . .
C9 C 1.14725(14) -0.01969(15) 0.1617(4) 0.0369(10) Uani 1 1 d . . . . .
H3 H 1.1653 -0.0500 0.1538 0.044 Uiso 1 1 calc R U . . .
C10 C 1.17142(15) 0.02486(15) 0.1403(4) 0.0395(10) Uani 1 1 d . . . . .
H6 H 1.2059 0.0249 0.1177 0.047 Uiso 1 1 calc R U . . .
C11 C 1.14599(15) 0.06974(16) 0.1512(4) 0.0411(10) Uani 1 1 d . . . . .
H4 H 1.1629 0.1004 0.1367 0.049 Uiso 1 1 calc R U . . .
C12 C 1.09593(14) 0.06932(15) 0.1834(4) 0.0358(9) Uani 1 1 d . . . . .
H5 H 1.0785 0.1000 0.1914 0.043 Uiso 1 1 calc R U . . .
C13 C 1.01948(17) -0.15927(16) 0.2587(4) 0.0486(12) Uani 1 1 d . . . . .
H7 H 1.0023 -0.1899 0.2711 0.058 Uiso 1 1 calc R U . . .
C14 C 0.99416(16) -0.11489(16) 0.2678(4) 0.0417(11) Uani 1 1 d . . . . .
H13 H 0.9595 -0.1152 0.2876 0.050 Uiso 1 1 calc R U . . .
C15 C 1.01855(14) -0.06865(15) 0.2483(4) 0.0344(9) Uani 1 1 d . . . . .
C17 C 0.93593(14) -0.02200(14) 0.2905(4) 0.0324(9) Uani 1 1 d . . . . .
C18 C 0.90102(15) -0.03378(16) 0.1919(4) 0.0449(11) Uani 1 1 d . . . . .
H12 H 0.9120 -0.0402 0.1025 0.054 Uiso 1 1 calc R U . . .
C19 C 0.85071(16) -0.03632(17) 0.2213(4) 0.0482(12) Uani 1 1 d . . . . .
H11 H 0.8276 -0.0449 0.1524 0.058 Uiso 1 1 calc R U . . .
C20 C 0.83392(15) -0.02658(15) 0.3491(4) 0.0410(10) Uani 1 1 d . . . . .
H10 H 0.7992 -0.0279 0.3686 0.049 Uiso 1 1 calc R U . . .
C21 C 0.86753(16) -0.01485(16) 0.4487(4) 0.0464(11) Uani 1 1 d . . . . .
H8 H 0.8561 -0.0080 0.5374 0.056 Uiso 1 1 calc R U . . .
C22 C 0.91791(15) -0.01303(15) 0.4195(4) 0.0432(11) Uani 1 1 d . . . . .
H9 H 0.9409 -0.0054 0.4896 0.052 Uiso 1 1 calc R U . . .
C23 C 0.97735(15) 0.10065(19) 0.1310(4) 0.0538(13) Uani 1 1 d . . . . .
H16 H 0.9857 0.0872 0.0453 0.065 Uiso 1 1 calc R U . . .
C24 C 0.95382(17) 0.1468(2) 0.1379(5) 0.0619(14) Uani 1 1 d . . . . .
H15 H 0.9465 0.1647 0.0576 0.074 Uiso 1 1 calc R U . . .
B1 B 0.99080(13) -0.02112(13) 0.2593(3) 0.0140(8) Uani 1 1 d . . . . .


_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
N1 B1 1.402(5) . ?
N1 C1A 1.482(5) . ?
N1 C5 1.534(5) . ?
C1 C2 1.371(6) . ?
C1 C13 1.390(6) . ?
C1 H1 0.9500 . ?
C1A C12 1.402(5) . ?
C1A C4 1.405(5) . ?
C2 C3 1.407(5) . ?
C2 H14 0.9500 . ?
C3 C15 1.414(5) . ?
C3 C4 1.472(5) . ?
C4 C9 1.414(5) . ?
C5 C6 1.375(5) . ?
C5 C23 1.381(6) . ?
C6 C7 1.387(6) . ?
C6 H17 0.9500 . ?
C7 C8 1.370(6) . ?
C7 H18 0.9500 . ?
C8 C24 1.360(7) . ?
C8 H2 0.9500 . ?
C9 C10 1.375(5) . ?
C9 H3 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H6 0.9500 . ?
C11 C12 1.379(5) . ?
C11 H4 0.9500 . ?
C12 H5 0.9500 . ?
C13 C14 1.372(6) . ?
C13 H7 0.9500 . ?
C14 C15 1.414(5) . ?
C14 H13 0.9500 . ?
C15 B1 1.479(5) . ?
C17 C22 1.389(5) . ?
C17 C18 1.390(5) . ?
C17 B1 1.502(5) . ?
C18 C19 1.381(6) . ?
C18 H12 0.9500 . ?
C19 C20 1.370(6) . ?
C19 H11 0.9500 . ?
C20 C21 1.373(6) . ?
C20 H10 0.9500 . ?
C21 C22 1.381(6) . ?
C21 H8 0.9500 . ?
C22 H9 0.9500 . ?
C23 C24 1.390(7) . ?
C23 H16 0.9500 . ?
C24 H15 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
B1 N1 C1A 121.4(3) . . ?
B1 N1 C5 120.6(3) . . ?
C1A N1 C5 118.0(3) . . ?
C2 C1 C13 120.2(4) . . ?
C2 C1 H1 119.9 . . ?
C13 C1 H1 119.9 . . ?
C12 C1A C4 119.9(3) . . ?
C12 C1A N1 121.3(3) . . ?
C4 C1A N1 118.8(3) . . ?
C1 C2 C3 121.4(4) . . ?
C1 C2 H14 119.3 . . ?
C3 C2 H14 119.3 . . ?
C2 C3 C15 118.6(3) . . ?
C2 C3 C4 122.2(3) . . ?
C15 C3 C4 119.2(3) . . ?
C1A C4 C9 117.7(3) . . ?
C1A C4 C3 121.0(3) . . ?
C9 C4 C3 121.2(3) . . ?
C6 C5 C23 117.3(4) . . ?
C6 C5 N1 121.2(4) . . ?
C23 C5 N1 121.4(4) . . ?
C5 C6 C7 121.7(4) . . ?
C5 C6 H17 119.2 . . ?
C7 C6 H17 119.2 . . ?
C8 C7 C6 119.6(5) . . ?
C8 C7 H18 120.2 . . ?
C6 C7 H18 120.2 . . ?
C24 C8 C7 120.1(5) . . ?
C24 C8 H2 120.0 . . ?
C7 C8 H2 120.0 . . ?
C10 C9 C4 121.3(4) . . ?
C10 C9 H3 119.4 . . ?
C4 C9 H3 119.4 . . ?
C9 C10 C11 120.6(4) . . ?
C9 C10 H6 119.7 . . ?
C11 C10 H6 119.7 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H4 120.3 . . ?
C10 C11 H4 120.3 . . ?
C11 C12 C1A 121.2(4) . . ?
C11 C12 H5 119.4 . . ?
C1A C12 H5 119.4 . . ?
C14 C13 C1 119.8(4) . . ?
C14 C13 H7 120.1 . . ?
C1 C13 H7 120.1 . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H13 119.3 . . ?
C15 C14 H13 119.3 . . ?
C14 C15 C3 118.4(4) . . ?
C14 C15 B1 120.8(3) . . ?
C3 C15 B1 120.8(3) . . ?
C22 C17 C18 117.0(4) . . ?
C22 C17 B1 121.8(3) . . ?
C18 C17 B1 121.1(3) . . ?
C19 C18 C17 121.3(4) . . ?
C19 C18 H12 119.4 . . ?
C17 C18 H12 119.4 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H11 119.8 . . ?
C18 C19 H11 119.8 . . ?
C19 C20 C21 119.6(4) . . ?
C19 C20 H10 120.2 . . ?
C21 C20 H10 120.2 . . ?
C20 C21 C22 119.9(4) . . ?
C20 C21 H8 120.1 . . ?
C22 C21 H8 120.1 . . ?
C21 C22 C17 121.8(4) . . ?
C21 C22 H9 119.1 . . ?
C17 C22 H9 119.1 . . ?
C5 C23 C24 121.5(4) . . ?
C5 C23 H16 119.3 . . ?
C24 C23 H16 119.3 . . ?
C8 C24 C23 119.8(4) . . ?
C8 C24 H15 120.1 . . ?
C23 C24 H15 120.1 . . ?
N1 B1 C15 118.8(3) . . ?
N1 B1 C17 121.6(3) . . ?
C15 B1 C17 119.6(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
B1 N1 C1A C12 180.0(3) . . . . ?
C5 N1 C1A C12 1.6(5) . . . . ?
B1 N1 C1A C4 -0.9(5) . . . . ?
C5 N1 C1A C4 -179.2(3) . . . . ?
C13 C1 C2 C3 -1.3(6) . . . . ?
C1 C2 C3 C15 2.0(6) . . . . ?
C1 C2 C3 C4 -177.9(4) . . . . ?
C12 C1A C4 C9 -1.4(5) . . . . ?
N1 C1A C4 C9 179.4(3) . . . . ?
C12 C1A C4 C3 179.1(3) . . . . ?
N1 C1A C4 C3 -0.1(5) . . . . ?
C2 C3 C4 C1A -178.7(3) . . . . ?
C15 C3 C4 C1A 1.4(5) . . . . ?
C2 C3 C4 C9 1.8(5) . . . . ?
C15 C3 C4 C9 -178.1(3) . . . . ?
B1 N1 C5 C6 76.4(5) . . . . ?
C1A N1 C5 C6 -105.2(4) . . . . ?
B1 N1 C5 C23 -105.2(4) . . . . ?
C1A N1 C5 C23 73.2(5) . . . . ?
C23 C5 C6 C7 0.2(7) . . . . ?
N1 C5 C6 C7 178.7(4) . . . . ?
C5 C6 C7 C8 -0.8(8) . . . . ?
C6 C7 C8 C24 0.7(8) . . . . ?
C1A C4 C9 C10 0.8(5) . . . . ?
C3 C4 C9 C10 -179.7(3) . . . . ?
C4 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 -0.3(6) . . . . ?
C10 C11 C12 C1A -0.3(6) . . . . ?
C4 C1A C12 C11 1.2(5) . . . . ?
N1 C1A C12 C11 -179.6(3) . . . . ?
C2 C1 C13 C14 -0.1(6) . . . . ?
C1 C13 C14 C15 0.8(6) . . . . ?
C13 C14 C15 C3 -0.1(6) . . . . ?
C13 C14 C15 B1 -179.6(4) . . . . ?
C2 C3 C15 C14 -1.3(5) . . . . ?
C4 C3 C15 C14 178.6(3) . . . . ?
C2 C3 C15 B1 178.3(3) . . . . ?
C4 C3 C15 B1 -1.8(5) . . . . ?
C22 C17 C18 C19 0.1(6) . . . . ?
B1 C17 C18 C19 177.7(4) . . . . ?
C17 C18 C19 C20 0.8(7) . . . . ?
C18 C19 C20 C21 -0.8(7) . . . . ?
C19 C20 C21 C22 -0.1(6) . . . . ?
C20 C21 C22 C17 1.1(6) . . . . ?
C18 C17 C22 C21 -1.0(6) . . . . ?
B1 C17 C22 C21 -178.7(4) . . . . ?
C6 C5 C23 C24 0.5(6) . . . . ?
N1 C5 C23 C24 -178.0(4) . . . . ?
C7 C8 C24 C23 0.0(7) . . . . ?
C5 C23 C24 C8 -0.6(7) . . . . ?
C1A N1 B1 C15 0.5(5) . . . . ?
C5 N1 B1 C15 178.8(3) . . . . ?
C1A N1 B1 C17 -178.6(3) . . . . ?
C5 N1 B1 C17 -0.3(5) . . . . ?
C14 C15 B1 N1 -179.6(3) . . . . ?
C3 C15 B1 N1 0.9(5) . . . . ?
C14 C15 B1 C17 -0.5(5) . . . . ?
C3 C15 B1 C17 180.0(3) . . . . ?
C22 C17 B1 N1 -80.7(5) . . . . ?
C18 C17 B1 N1 101.8(4) . . . . ?
C22 C17 B1 C15 100.3(4) . . . . ?
C18 C17 B1 C15 -77.3(5) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_10Cl
_database_code_depnum_ccdc_archive 'CCDC 1819490'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            10Cl
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 B Cl N'
_chemical_formula_sum            'C22 H23 B Cl N'
_chemical_formula_weight         347.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.6790(15)
_cell_length_b                   12.5898(13)
_cell_length_c                   10.2613(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.732(3)
_cell_angle_gamma                90
_cell_volume                     1751.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      28.16

_exptl_crystal_description       blocklike
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56105
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.208
_diffrn_reflns_theta_max         27.874
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4179
_reflns_number_gt                3119
_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 (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)+(0.0562P)²+0.4821P] 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         4179
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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
Cl1 Cl 0.04934(3) 0.70686(4) 0.07619(5) 0.03095(15) Uani 1 1 d . . . . .
N1 N 0.24731(10) 0.77809(11) 0.10697(13) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.30655(18) 0.39311(15) 0.25319(19) 0.0395(5) Uani 1 1 d . . . . .
H6 H 0.3351 0.3302 0.2927 0.047 Uiso 1 1 calc R U . . .
C5 C 0.36693(16) 0.47428(15) 0.21967(18) 0.0337(5) Uani 1 1 d . . . . .
H5 H 0.4366 0.4666 0.2357 0.040 Uiso 1 1 calc R U . . .
C13 C 0.32527(14) 0.56794(13) 0.16203(16) 0.0245(4) Uani 1 1 d . . . . .
C14 C 0.22209(13) 0.58083(13) 0.14494(16) 0.0232(4) Uani 1 1 d . . . . .
C15 C 0.22610(11) 0.89245(13) 0.14097(16) 0.0177(3) Uani 1 1 d . . . . .
C23 C 0.16627(12) 0.94819(13) 0.02447(16) 0.0200(4) Uani 1 1 d . . . . .
H17 H 0.1049 0.9078 -0.0034 0.024 Uiso 1 1 calc R U . . .
H16 H 0.2049 0.9504 -0.0504 0.024 Uiso 1 1 calc R U . . .
C19 C 0.14042(13) 1.06133(13) 0.06184(17) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.1011 1.0968 -0.0152 0.028 Uiso 1 1 calc R U . . .
C18 C 0.23600(13) 1.12309(14) 0.10199(17) 0.0253(4) Uani 1 1 d . . . . .
H12 H 0.2204 1.1975 0.1229 0.030 Uiso 1 1 calc R U . . .
H25 H 0.2759 1.1239 0.0283 0.030 Uiso 1 1 calc R U . . .
C20 C 0.08015(13) 1.05780(14) 0.17737(17) 0.0259(4) Uani 1 1 d . . . . .
H14 H 0.0615 1.1308 0.2000 0.031 Uiso 1 1 calc R U . . .
H15 H 0.0189 1.0166 0.1521 0.031 Uiso 1 1 calc R U . . .
C21 C 0.14097(13) 1.00604(14) 0.29667(16) 0.0233(4) Uani 1 1 d . . . . .
H20 H 0.1010 1.0036 0.3714 0.028 Uiso 1 1 calc R U . . .
C24 C 0.23438(13) 1.07059(14) 0.33722(17) 0.0255(4) Uani 1 1 d . . . . .
H22 H 0.2731 1.0387 0.4160 0.031 Uiso 1 1 calc R U . . .
H21 H 0.2170 1.1443 0.3588 0.031 Uiso 1 1 calc R U . . .
C17 C 0.29478(13) 1.07063(13) 0.22255(17) 0.0235(4) Uani 1 1 d . . . . .
H10 H 0.3570 1.1117 0.2483 0.028 Uiso 1 1 calc R U . . .
C16 C 0.32126(12) 0.95632(13) 0.18833(17) 0.0219(4) Uani 1 1 d . . . . .
H26 H 0.3578 0.9216 0.2668 0.026 Uiso 1 1 calc R U . . .
H9 H 0.3644 0.9573 0.1182 0.026 Uiso 1 1 calc R U . . .
C7 C 0.20504(18) 0.40301(15) 0.22954(19) 0.0382(5) Uani 1 1 d . . . . .
H7 H 0.1642 0.3459 0.2494 0.046 Uiso 1 1 calc R U . . .
C8 C 0.16317(16) 0.49581(14) 0.17714(17) 0.0301(4) Uani 1 1 d . . . . .
H8 H 0.0934 0.5024 0.1625 0.036 Uiso 1 1 calc R U . . .
C12 C 0.38344(13) 0.65015(14) 0.10593(16) 0.0233(4) Uani 1 1 d . . . . .
C4 C 0.47726(13) 0.62798(15) 0.07181(18) 0.0295(4) Uani 1 1 d . . . . .
H4 H 0.5079 0.5624 0.0987 0.035 Uiso 1 1 calc R U . . .
C3 C 0.52639(14) 0.69782(16) 0.00082(19) 0.0339(5) Uani 1 1 d . . . . .
H3 H 0.5915 0.6827 -0.0162 0.041 Uiso 1 1 calc R U . . .
C2 C 0.47959(14) 0.79059(17) -0.04558(19) 0.0321(4) Uani 1 1 d . . . . .
H2 H 0.5109 0.8372 -0.0999 0.038 Uiso 1 1 calc R U . . .
C1 C 0.38732(13) 0.81552(15) -0.01309(17) 0.0255(4) Uani 1 1 d . . . . .
H1 H 0.3550 0.8782 -0.0477 0.031 Uiso 1 1 calc R U . . .
C11 C 0.34092(12) 0.74997(14) 0.06984(16) 0.0205(4) Uani 1 1 d . . . . .
C22 C 0.16793(12) 0.89231(13) 0.26017(16) 0.0209(4) Uani 1 1 d . . . . .
H18 H 0.1069 0.8500 0.2387 0.025 Uiso 1 1 calc R U . . .
H19 H 0.2084 0.8587 0.3364 0.025 Uiso 1 1 calc R U . . .
B1 B 0.18100(15) 0.69207(16) 0.10984(19) 0.0219(4) Uani 1 1 d . . . . .


_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
Cl1 B1 1.797(2) . ?
N1 B1 1.416(2) . ?
N1 C11 1.429(2) . ?
N1 C15 1.519(2) . ?
C6 C7 1.383(3) . ?
C6 C5 1.386(3) . ?
C6 H6 0.9500 . ?
C5 C13 1.405(2) . ?
C5 H5 0.9500 . ?
C13 C14 1.408(3) . ?
C13 C12 1.469(3) . ?
C14 C8 1.406(3) . ?
C14 B1 1.534(3) . ?
C15 C23 1.526(2) . ?
C15 C22 1.546(2) . ?
C15 C16 1.551(2) . ?
C23 C19 1.529(2) . ?
C23 H17 0.9900 . ?
C23 H16 0.9900 . ?
C19 C18 1.529(3) . ?
C19 C20 1.533(2) . ?
C19 H13 1.0000 . ?
C18 C17 1.531(2) . ?
C18 H12 0.9900 . ?
C18 H25 0.9900 . ?
C20 C21 1.530(2) . ?
C20 H14 0.9900 . ?
C20 H15 0.9900 . ?
C21 C24 1.524(2) . ?
C21 C22 1.537(2) . ?
C21 H20 1.0000 . ?
C24 C17 1.526(2) . ?
C24 H22 0.9900 . ?
C24 H21 0.9900 . ?
C17 C16 1.536(2) . ?
C17 H10 1.0000 . ?
C16 H26 0.9900 . ?
C16 H9 0.9900 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C12 C4 1.403(2) . ?
C12 C11 1.413(2) . ?
C4 C3 1.374(3) . ?
C4 H4 0.9500 . ?
C3 C2 1.385(3) . ?
C3 H3 0.9500 . ?
C2 C1 1.384(2) . ?
C2 H2 0.9500 . ?
C1 C11 1.398(2) . ?
C1 H1 0.9500 . ?
C22 H18 0.9900 . ?
C22 H19 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
B1 N1 C11 114.57(14) . . ?
B1 N1 C15 125.30(14) . . ?
C11 N1 C15 120.13(13) . . ?
C7 C6 C5 120.53(18) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C5 C13 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C13 C5 H5 119.9 . . ?
C5 C13 C14 119.48(18) . . ?
C5 C13 C12 123.08(18) . . ?
C14 C13 C12 117.17(15) . . ?
C8 C14 C13 118.67(16) . . ?
C8 C14 B1 123.16(17) . . ?
C13 C14 B1 117.65(15) . . ?
N1 C15 C23 110.79(13) . . ?
N1 C15 C22 108.38(13) . . ?
C23 C15 C22 109.97(13) . . ?
N1 C15 C16 112.65(13) . . ?
C23 C15 C16 110.24(13) . . ?
C22 C15 C16 104.60(13) . . ?
C15 C23 C19 110.47(14) . . ?
C15 C23 H17 109.6 . . ?
C19 C23 H17 109.6 . . ?
C15 C23 H16 109.6 . . ?
C19 C23 H16 109.6 . . ?
H17 C23 H16 108.1 . . ?
C23 C19 C18 108.85(14) . . ?
C23 C19 C20 109.49(14) . . ?
C18 C19 C20 109.61(14) . . ?
C23 C19 H13 109.6 . . ?
C18 C19 H13 109.6 . . ?
C20 C19 H13 109.6 . . ?
C19 C18 C17 109.59(14) . . ?
C19 C18 H12 109.8 . . ?
C17 C18 H12 109.8 . . ?
C19 C18 H25 109.8 . . ?
C17 C18 H25 109.8 . . ?
H12 C18 H25 108.2 . . ?
C21 C20 C19 109.88(14) . . ?
C21 C20 H14 109.7 . . ?
C19 C20 H14 109.7 . . ?
C21 C20 H15 109.7 . . ?
C19 C20 H15 109.7 . . ?
H14 C20 H15 108.2 . . ?
C24 C21 C20 109.69(14) . . ?
C24 C21 C22 110.08(14) . . ?
C20 C21 C22 108.91(14) . . ?
C24 C21 H20 109.4 . . ?
C20 C21 H20 109.4 . . ?
C22 C21 H20 109.4 . . ?
C21 C24 C17 108.09(14) . . ?
C21 C24 H22 110.1 . . ?
C17 C24 H22 110.1 . . ?
C21 C24 H21 110.1 . . ?
C17 C24 H21 110.1 . . ?
H22 C24 H21 108.4 . . ?
C24 C17 C18 110.07(15) . . ?
C24 C17 C16 110.16(14) . . ?
C18 C17 C16 109.49(14) . . ?
C24 C17 H10 109.0 . . ?
C18 C17 H10 109.0 . . ?
C16 C17 H10 109.0 . . ?
C17 C16 C15 110.08(13) . . ?
C17 C16 H26 109.6 . . ?
C15 C16 H26 109.6 . . ?
C17 C16 H9 109.6 . . ?
C15 C16 H9 109.6 . . ?
H26 C16 H9 108.2 . . ?
C8 C7 C6 119.98(19) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C14 121.1(2) . . ?
C7 C8 H8 119.5 . . ?
C14 C8 H8 119.5 . . ?
C4 C12 C11 118.01(16) . . ?
C4 C12 C13 121.29(16) . . ?
C11 C12 C13 120.24(15) . . ?
C3 C4 C12 122.29(17) . . ?
C3 C4 H4 118.9 . . ?
C12 C4 H4 118.9 . . ?
C4 C3 C2 119.05(17) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C1 C2 C3 120.17(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C1 C11 121.08(17) . . ?
C2 C1 H1 119.5 . . ?
C11 C1 H1 119.5 . . ?
C1 C11 C12 118.69(15) . . ?
C1 C11 N1 120.84(15) . . ?
C12 C11 N1 120.17(15) . . ?
C21 C22 C15 110.95(13) . . ?
C21 C22 H18 109.4 . . ?
C15 C22 H18 109.4 . . ?
C21 C22 H19 109.4 . . ?
C15 C22 H19 109.4 . . ?
H18 C22 H19 108.0 . . ?
N1 B1 C14 119.20(16) . . ?
N1 B1 Cl1 123.03(14) . . ?
C14 B1 Cl1 117.76(14) . . ?

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
C7 C6 C5 C13 0.5(3) . . . . ?
C6 C5 C13 C14 3.3(3) . . . . ?
C6 C5 C13 C12 -170.50(16) . . . . ?
C5 C13 C14 C8 -4.8(2) . . . . ?
C12 C13 C14 C8 169.37(15) . . . . ?
C5 C13 C14 B1 167.14(15) . . . . ?
C12 C13 C14 B1 -18.7(2) . . . . ?
B1 N1 C15 C23 -81.37(19) . . . . ?
C11 N1 C15 C23 99.42(16) . . . . ?
B1 N1 C15 C22 39.4(2) . . . . ?
C11 N1 C15 C22 -139.85(14) . . . . ?
B1 N1 C15 C16 154.61(15) . . . . ?
C11 N1 C15 C16 -24.6(2) . . . . ?
N1 C15 C23 C19 176.92(13) . . . . ?
C22 C15 C23 C19 57.14(18) . . . . ?
C16 C15 C23 C19 -57.69(17) . . . . ?
C15 C23 C19 C18 60.31(17) . . . . ?
C15 C23 C19 C20 -59.49(18) . . . . ?
C23 C19 C18 C17 -61.79(18) . . . . ?
C20 C19 C18 C17 57.93(18) . . . . ?
C23 C19 C20 C21 61.08(18) . . . . ?
C18 C19 C20 C21 -58.25(18) . . . . ?
C19 C20 C21 C24 60.41(18) . . . . ?
C19 C20 C21 C22 -60.12(18) . . . . ?
C20 C21 C24 C17 -61.34(18) . . . . ?
C22 C21 C24 C17 58.48(18) . . . . ?
C21 C24 C17 C18 61.44(18) . . . . ?
C21 C24 C17 C16 -59.40(18) . . . . ?
C19 C18 C17 C24 -60.23(18) . . . . ?
C19 C18 C17 C16 61.01(18) . . . . ?
C24 C17 C16 C15 63.35(18) . . . . ?
C18 C17 C16 C15 -57.84(18) . . . . ?
N1 C15 C16 C17 -179.37(13) . . . . ?
C23 C15 C16 C17 56.31(17) . . . . ?
C22 C15 C16 C17 -61.87(17) . . . . ?
C5 C6 C7 C8 -2.6(3) . . . . ?
C6 C7 C8 C14 1.0(3) . . . . ?
C13 C14 C8 C7 2.7(3) . . . . ?
B1 C14 C8 C7 -168.78(17) . . . . ?
C5 C13 C12 C4 18.7(3) . . . . ?
C14 C13 C12 C4 -155.17(16) . . . . ?
C5 C13 C12 C11 -169.21(16) . . . . ?
C14 C13 C12 C11 16.9(2) . . . . ?
C11 C12 C4 C3 -2.6(3) . . . . ?
C13 C12 C4 C3 169.58(16) . . . . ?
C12 C4 C3 C2 -3.9(3) . . . . ?
C4 C3 C2 C1 4.3(3) . . . . ?
C3 C2 C1 C11 2.0(3) . . . . ?
C2 C1 C11 C12 -8.6(3) . . . . ?
C2 C1 C11 N1 177.66(16) . . . . ?
C4 C12 C11 C1 8.7(2) . . . . ?
C13 C12 C11 C1 -163.57(15) . . . . ?
C4 C12 C11 N1 -177.45(15) . . . . ?
C13 C12 C11 N1 10.2(2) . . . . ?
B1 N1 C11 C1 139.76(17) . . . . ?
C15 N1 C11 C1 -40.9(2) . . . . ?
B1 N1 C11 C12 -33.9(2) . . . . ?
C15 N1 C11 C12 145.37(15) . . . . ?
C24 C21 C22 C15 -62.20(18) . . . . ?
C20 C21 C22 C15 58.09(18) . . . . ?
N1 C15 C22 C21 -178.05(13) . . . . ?
C23 C15 C22 C21 -56.81(18) . . . . ?
C16 C15 C22 C21 61.56(17) . . . . ?
C11 N1 B1 C14 31.1(2) . . . . ?
C15 N1 B1 C14 -148.14(15) . . . . ?
C11 N1 B1 Cl1 -149.75(13) . . . . ?
C15 N1 B1 Cl1 31.0(2) . . . . ?
C8 C14 B1 N1 166.26(16) . . . . ?
C13 C14 B1 N1 -5.3(2) . . . . ?
C8 C14 B1 Cl1 -12.9(2) . . . . ?
C13 C14 B1 Cl1 175.56(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H18 Cl1 0.99 2.51 3.2899(18) 135.6 .
C22 H18 Cl1 0.99 2.51 3.2899(18) 135.6 .
C22 H18 Cl1 0.99 2.51 3.2899(18) 135.6 .

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.103

_shelxl_version_number           2013-4

_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_10Ph
_database_code_depnum_ccdc_archive 'CCDC 1819491'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            10Ph
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 B N'
_chemical_formula_sum            'C28 H28 B N'
_chemical_formula_weight         389.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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                   15.8892(14)
_cell_length_b                   12.4193(10)
_cell_length_c                   11.0719(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.771(3)
_cell_angle_gamma                90
_cell_volume                     2112.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.64

_exptl_crystal_description       blocklike
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70986
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.512
_diffrn_reflns_theta_max         27.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4675
_reflns_number_gt                2841
_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 (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)+(0.0345P)²+0.8354P] 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         4675
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
N1 N 0.22076(9) 0.26800(11) 0.92349(12) 0.0232(3) Uani 1 1 d . . . . .
C19 C 0.55578(13) 0.15510(17) 0.9876(2) 0.0455(5) Uani 1 1 d . . . . .
H19 H 0.6174 0.1490 1.0067 0.055 Uiso 1 1 calc R U . . .
C20 C 0.50667(13) 0.14333(16) 0.8666(2) 0.0430(5) Uani 1 1 d . . . . .
H20 H 0.5344 0.1293 0.8017 0.052 Uiso 1 1 calc R U . . .
C21 C 0.41721(12) 0.15179(15) 0.83911(17) 0.0336(5) Uani 1 1 d . . . . .
H21 H 0.3843 0.1412 0.7554 0.040 Uiso 1 1 calc R U . . .
C15 C 0.37337(11) 0.17540(13) 0.93047(15) 0.0252(4) Uani 1 1 d . . . . .
C11 C 0.14083(11) 0.24804(14) 0.95711(15) 0.0250(4) Uani 1 1 d . . . . .
C1 C 0.11083(11) 0.31811(15) 1.03617(15) 0.0302(4) Uani 1 1 d . . . . .
H1 H 0.1454 0.3784 1.0709 0.036 Uiso 1 1 calc R U . . .
C2 C 0.03240(12) 0.30156(16) 1.06475(16) 0.0354(5) Uani 1 1 d . . . . .
H2 H 0.0128 0.3515 1.1166 0.042 Uiso 1 1 calc R U . . .
C3 C -0.01780(12) 0.21305(16) 1.01857(17) 0.0365(5) Uani 1 1 d . . . . .
H3 H -0.0732 0.2034 1.0347 0.044 Uiso 1 1 calc R U . . .
C24 C 0.23701(13) 0.61746(14) 0.92450(17) 0.0351(5) Uani 1 1 d . . . . .
H26 H 0.2507 0.6923 0.9052 0.042 Uiso 1 1 calc R U . . .
H25 H 0.2038 0.6200 0.9889 0.042 Uiso 1 1 calc R U . . .
C25 C 0.32118(12) 0.55471(14) 0.97410(16) 0.0320(4) Uani 1 1 d . . . . .
H27 H 0.3575 0.5917 1.0498 0.038 Uiso 1 1 calc R U . . .
C26 C 0.37158(13) 0.54962(15) 0.87346(17) 0.0368(5) Uani 1 1 d . . . . .
H29 H 0.3867 0.6233 0.8521 0.044 Uiso 1 1 calc R U . . .
H28 H 0.4263 0.5087 0.9050 0.044 Uiso 1 1 calc R U . . .
C29 C 0.31520(12) 0.49443(14) 0.75732(16) 0.0324(4) Uani 1 1 d . . . . .
H34 H 0.3485 0.4899 0.6921 0.039 Uiso 1 1 calc R U . . .
C28 C 0.29288(12) 0.38059(13) 0.79208(16) 0.0275(4) Uani 1 1 d . . . . .
H33 H 0.3472 0.3387 0.8222 0.033 Uiso 1 1 calc R U . . .
H32 H 0.2570 0.3441 0.7169 0.033 Uiso 1 1 calc R U . . .
C16 C 0.24270(11) 0.38298(13) 0.89451(15) 0.0230(4) Uani 1 1 d . . . . .
C18 C 0.51464(12) 0.17592(16) 1.08094(18) 0.0394(5) Uani 1 1 d . . . . .
H18 H 0.5480 0.1830 1.1650 0.047 Uiso 1 1 calc R U . . .
C17 C 0.42486(11) 0.18651(14) 1.05248(16) 0.0291(4) Uani 1 1 d . . . . .
H17 H 0.3977 0.2017 1.1177 0.035 Uiso 1 1 calc R U . . .
C14 C 0.21994(11) 0.07035(13) 0.86519(15) 0.0260(4) Uani 1 1 d . . . . .
C13 C 0.13005(12) 0.06711(13) 0.85576(15) 0.0271(4) Uani 1 1 d . . . . .
C5 C 0.08056(13) -0.01914(15) 0.79428(17) 0.0376(5) Uani 1 1 d . . . . .
H5 H 0.0195 -0.0201 0.7857 0.045 Uiso 1 1 calc R U . . .
C6 C 0.11871(15) -0.10237(16) 0.74617(17) 0.0436(5) Uani 1 1 d . . . . .
H6 H 0.0840 -0.1598 0.7036 0.052 Uiso 1 1 calc R U . . .
C7 C 0.20783(15) -0.10264(15) 0.75963(17) 0.0413(5) Uani 1 1 d . . . . .
H7 H 0.2346 -0.1612 0.7286 0.050 Uiso 1 1 calc R U . . .
C8 C 0.25760(13) -0.01745(14) 0.81829(16) 0.0326(4) Uani 1 1 d . . . . .
H8 H 0.3187 -0.0182 0.8272 0.039 Uiso 1 1 calc R U . . .
C12 C 0.09346(11) 0.15265(14) 0.91744(15) 0.0261(4) Uani 1 1 d . . . . .
C4 C 0.01352(11) 0.13897(15) 0.94880(17) 0.0332(5) Uani 1 1 d . . . . .
H4 H -0.0199 0.0762 0.9206 0.040 Uiso 1 1 calc R U . . .
C22 C 0.15943(11) 0.44842(14) 0.83831(16) 0.0289(4) Uani 1 1 d . . . . .
H22 H 0.1252 0.4123 0.7618 0.035 Uiso 1 1 calc R U . . .
H23 H 0.1232 0.4514 0.8989 0.035 Uiso 1 1 calc R U . . .
C23 C 0.18210(13) 0.56315(14) 0.80624(16) 0.0324(4) Uani 1 1 d . . . . .
H24 H 0.1272 0.6050 0.7742 0.039 Uiso 1 1 calc R U . . .
C30 C 0.23237(13) 0.55952(15) 0.70630(16) 0.0358(5) Uani 1 1 d . . . . .
H35 H 0.2472 0.6334 0.6854 0.043 Uiso 1 1 calc R U . . .
H36 H 0.1965 0.5253 0.6295 0.043 Uiso 1 1 calc R U . . .
C27 C 0.30003(11) 0.44011(14) 1.00896(15) 0.0266(4) Uani 1 1 d . . . . .
H31 H 0.3547 0.3992 1.0404 0.032 Uiso 1 1 calc R U . . .
H30 H 0.2693 0.4431 1.0762 0.032 Uiso 1 1 calc R U . . .
B1 B 0.27115(13) 0.17624(16) 0.90713(17) 0.0249(4) Uani 1 1 d . . . . .


_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
N1 B1 1.431(2) . ?
N1 C11 1.433(2) . ?
N1 C16 1.523(2) . ?
C19 C20 1.375(3) . ?
C19 C18 1.381(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C15 1.398(2) . ?
C21 H21 0.9500 . ?
C15 C17 1.396(2) . ?
C15 B1 1.578(3) . ?
C11 C1 1.401(2) . ?
C11 C12 1.412(2) . ?
C1 C2 1.377(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C24 C25 1.524(3) . ?
C24 C23 1.532(3) . ?
C24 H26 0.9900 . ?
C24 H25 0.9900 . ?
C25 C26 1.530(3) . ?
C25 C27 1.534(2) . ?
C25 H27 1.0000 . ?
C26 C29 1.529(3) . ?
C26 H29 0.9900 . ?
C26 H28 0.9900 . ?
C29 C30 1.525(3) . ?
C29 C28 1.531(2) . ?
C29 H34 1.0000 . ?
C28 C16 1.544(2) . ?
C28 H33 0.9900 . ?
C28 H32 0.9900 . ?
C16 C27 1.533(2) . ?
C16 C22 1.542(2) . ?
C18 C17 1.387(2) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C14 C8 1.405(2) . ?
C14 C13 1.406(2) . ?
C14 B1 1.554(3) . ?
C13 C5 1.399(2) . ?
C13 C12 1.461(2) . ?
C5 C6 1.373(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C12 C4 1.410(2) . ?
C4 H4 0.9500 . ?
C22 C23 1.533(2) . ?
C22 H22 0.9900 . ?
C22 H23 0.9900 . ?
C23 C30 1.522(2) . ?
C23 H24 1.0000 . ?
C30 H35 0.9900 . ?
C30 H36 0.9900 . ?
C27 H31 0.9900 . ?
C27 H30 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
B1 N1 C11 117.18(14) . . ?
B1 N1 C16 123.68(13) . . ?
C11 N1 C16 118.84(13) . . ?
C20 C19 C18 119.32(18) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.23(19) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C15 122.13(18) . . ?
C20 C21 H21 118.9 . . ?
C15 C21 H21 118.9 . . ?
C17 C15 C21 116.34(16) . . ?
C17 C15 B1 118.85(15) . . ?
C21 C15 B1 124.39(15) . . ?
C1 C11 C12 118.43(15) . . ?
C1 C11 N1 121.32(15) . . ?
C12 C11 N1 120.11(15) . . ?
C2 C1 C11 121.51(17) . . ?
C2 C1 H1 119.2 . . ?
C11 C1 H1 119.2 . . ?
C1 C2 C3 120.40(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 118.99(17) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C25 C24 C23 109.81(15) . . ?
C25 C24 H26 109.7 . . ?
C23 C24 H26 109.7 . . ?
C25 C24 H25 109.7 . . ?
C23 C24 H25 109.7 . . ?
H26 C24 H25 108.2 . . ?
C24 C25 C26 109.44(15) . . ?
C24 C25 C27 109.67(15) . . ?
C26 C25 C27 109.49(15) . . ?
C24 C25 H27 109.4 . . ?
C26 C25 H27 109.4 . . ?
C27 C25 H27 109.4 . . ?
C29 C26 C25 109.13(15) . . ?
C29 C26 H29 109.9 . . ?
C25 C26 H29 109.9 . . ?
C29 C26 H28 109.9 . . ?
C25 C26 H28 109.9 . . ?
H29 C26 H28 108.3 . . ?
C30 C29 C26 109.82(15) . . ?
C30 C29 C28 110.45(15) . . ?
C26 C29 C28 109.04(14) . . ?
C30 C29 H34 109.2 . . ?
C26 C29 H34 109.2 . . ?
C28 C29 H34 109.2 . . ?
C29 C28 C16 111.29(14) . . ?
C29 C28 H33 109.4 . . ?
C16 C28 H33 109.4 . . ?
C29 C28 H32 109.4 . . ?
C16 C28 H32 109.4 . . ?
H33 C28 H32 108.0 . . ?
N1 C16 C27 112.30(13) . . ?
N1 C16 C22 111.10(13) . . ?
C27 C16 C22 110.94(14) . . ?
N1 C16 C28 109.00(13) . . ?
C27 C16 C28 107.87(14) . . ?
C22 C16 C28 105.33(13) . . ?
C19 C18 C17 120.23(18) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C17 C15 121.71(17) . . ?
C18 C17 H17 119.1 . . ?
C15 C17 H17 119.1 . . ?
C8 C14 C13 118.07(16) . . ?
C8 C14 B1 121.82(16) . . ?
C13 C14 B1 119.41(15) . . ?
C5 C13 C14 119.51(17) . . ?
C5 C13 C12 122.88(17) . . ?
C14 C13 C12 117.53(15) . . ?
C6 C5 C13 121.10(19) . . ?
C6 C5 H5 119.5 . . ?
C13 C5 H5 119.5 . . ?
C5 C6 C7 120.03(19) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.74(19) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C14 121.46(19) . . ?
C7 C8 H8 119.3 . . ?
C14 C8 H8 119.3 . . ?
C4 C12 C11 117.82(16) . . ?
C4 C12 C13 121.22(16) . . ?
C11 C12 C13 120.74(15) . . ?
C3 C4 C12 122.42(18) . . ?
C3 C4 H4 118.8 . . ?
C12 C4 H4 118.8 . . ?
C23 C22 C16 110.80(15) . . ?
C23 C22 H22 109.5 . . ?
C16 C22 H22 109.5 . . ?
C23 C22 H23 109.5 . . ?
C16 C22 H23 109.5 . . ?
H22 C22 H23 108.1 . . ?
C30 C23 C24 110.15(16) . . ?
C30 C23 C22 109.80(14) . . ?
C24 C23 C22 109.11(14) . . ?
C30 C23 H24 109.3 . . ?
C24 C23 H24 109.3 . . ?
C22 C23 H24 109.3 . . ?
C23 C30 C29 108.05(14) . . ?
C23 C30 H35 110.1 . . ?
C29 C30 H35 110.1 . . ?
C23 C30 H36 110.1 . . ?
C29 C30 H36 110.1 . . ?
H35 C30 H36 108.4 . . ?
C16 C27 C25 110.09(14) . . ?
C16 C27 H31 109.6 . . ?
C25 C27 H31 109.6 . . ?
C16 C27 H30 109.6 . . ?
C25 C27 H30 109.6 . . ?
H31 C27 H30 108.2 . . ?
N1 B1 C14 116.40(16) . . ?
N1 B1 C15 124.77(16) . . ?
C14 B1 C15 118.81(15) . . ?

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
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C15 1.9(3) . . . . ?
C20 C21 C15 C17 -2.1(3) . . . . ?
C20 C21 C15 B1 -174.48(18) . . . . ?
B1 N1 C11 C1 145.58(16) . . . . ?
C16 N1 C11 C1 -40.5(2) . . . . ?
B1 N1 C11 C12 -30.1(2) . . . . ?
C16 N1 C11 C12 143.78(15) . . . . ?
C12 C11 C1 C2 -6.8(2) . . . . ?
N1 C11 C1 C2 177.39(15) . . . . ?
C11 C1 C2 C3 1.9(3) . . . . ?
C1 C2 C3 C4 3.2(3) . . . . ?
C23 C24 C25 C26 58.51(19) . . . . ?
C23 C24 C25 C27 -61.63(19) . . . . ?
C24 C25 C26 C29 -59.30(19) . . . . ?
C27 C25 C26 C29 60.95(19) . . . . ?
C25 C26 C29 C30 61.38(19) . . . . ?
C25 C26 C29 C28 -59.77(19) . . . . ?
C30 C29 C28 C16 -60.99(18) . . . . ?
C26 C29 C28 C16 59.78(19) . . . . ?
B1 N1 C16 C27 -92.17(18) . . . . ?
C11 N1 C16 C27 94.35(17) . . . . ?
B1 N1 C16 C22 142.92(15) . . . . ?
C11 N1 C16 C22 -30.56(19) . . . . ?
B1 N1 C16 C28 27.3(2) . . . . ?
C11 N1 C16 C28 -146.19(14) . . . . ?
C29 C28 C16 N1 178.92(14) . . . . ?
C29 C28 C16 C27 -58.90(18) . . . . ?
C29 C28 C16 C22 59.63(18) . . . . ?
C20 C19 C18 C17 -1.0(3) . . . . ?
C19 C18 C17 C15 0.8(3) . . . . ?
C21 C15 C17 C18 0.7(3) . . . . ?
B1 C15 C17 C18 173.58(17) . . . . ?
C8 C14 C13 C5 -3.7(2) . . . . ?
B1 C14 C13 C5 166.89(15) . . . . ?
C8 C14 C13 C12 173.12(14) . . . . ?
B1 C14 C13 C12 -16.3(2) . . . . ?
C14 C13 C5 C6 1.9(3) . . . . ?
C12 C13 C5 C6 -174.71(16) . . . . ?
C13 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -1.9(3) . . . . ?
C6 C7 C8 C14 0.0(3) . . . . ?
C13 C14 C8 C7 2.8(2) . . . . ?
B1 C14 C8 C7 -167.58(16) . . . . ?
C1 C11 C12 C4 6.7(2) . . . . ?
N1 C11 C12 C4 -177.50(14) . . . . ?
C1 C11 C12 C13 -168.00(15) . . . . ?
N1 C11 C12 C13 7.8(2) . . . . ?
C5 C13 C12 C4 17.8(2) . . . . ?
C14 C13 C12 C4 -158.92(15) . . . . ?
C5 C13 C12 C11 -167.72(16) . . . . ?
C14 C13 C12 C11 15.6(2) . . . . ?
C2 C3 C4 C12 -3.1(3) . . . . ?
C11 C12 C4 C3 -1.9(2) . . . . ?
C13 C12 C4 C3 172.79(16) . . . . ?
N1 C16 C22 C23 -178.53(13) . . . . ?
C27 C16 C22 C23 55.80(18) . . . . ?
C28 C16 C22 C23 -60.65(17) . . . . ?
C25 C24 C23 C30 -59.75(19) . . . . ?
C25 C24 C23 C22 60.84(19) . . . . ?
C16 C22 C23 C30 63.10(19) . . . . ?
C16 C22 C23 C24 -57.70(19) . . . . ?
C24 C23 C30 C29 60.51(19) . . . . ?
C22 C23 C30 C29 -59.67(19) . . . . ?
C26 C29 C30 C23 -61.53(19) . . . . ?
C28 C29 C30 C23 58.76(19) . . . . ?
N1 C16 C27 C25 179.18(14) . . . . ?
C22 C16 C27 C25 -55.82(18) . . . . ?
C28 C16 C27 C25 59.06(18) . . . . ?
C24 C25 C27 C16 58.76(18) . . . . ?
C26 C25 C27 C16 -61.34(19) . . . . ?
C11 N1 B1 C14 28.1(2) . . . . ?
C16 N1 B1 C14 -145.51(14) . . . . ?
C11 N1 B1 C15 -150.97(15) . . . . ?
C16 N1 B1 C15 35.4(2) . . . . ?
C8 C14 B1 N1 165.00(15) . . . . ?
C13 C14 B1 N1 -5.2(2) . . . . ?
C8 C14 B1 C15 -15.9(2) . . . . ?
C13 C14 B1 C15 173.88(14) . . . . ?
C17 C15 B1 N1 68.2(2) . . . . ?
C21 C15 B1 N1 -119.61(19) . . . . ?
C17 C15 B1 C14 -110.86(18) . . . . ?
C21 C15 B1 C14 61.4(2) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_1PhEt3PO
_database_code_depnum_ccdc_archive 'CCDC 1819493'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            1PhEt3PO
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H40 B O P'
_chemical_formula_sum            'C40 H40 B O P'
_chemical_formula_weight         578.50

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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.0948(3)
_cell_length_b                   36.1717(13)
_cell_length_c                   10.2433(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.991(2)
_cell_angle_gamma                90
_cell_volume                     3146.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.43

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64852
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6951
_reflns_number_gt                5256
_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 (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)+(0.0545P)²+1.0317P] 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         6951
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
P1 P 0.17244(5) 0.08798(2) 0.02763(5) 0.01864(12) Uani 1 1 d . . . . .
O1 O 0.33870(13) 0.07763(3) 0.12438(12) 0.0185(3) Uani 1 1 d . . . . .
C102 C 0.0071(2) 0.14081(5) -0.1685(2) 0.0310(4) Uani 1 1 d . . . . .
H10A H 0.0128 0.1650 -0.2096 0.046 Uiso 1 1 calc R U . . .
H10B H -0.0199 0.1219 -0.2417 0.046 Uiso 1 1 calc R U . . .
H10C H -0.0740 0.1414 -0.1262 0.046 Uiso 1 1 calc R U . . .
B1 B 0.4912(2) 0.10050(5) 0.1954(2) 0.0167(4) Uani 1 1 d . . . . .
C1 C 0.57013(19) 0.11491(4) 0.08560(17) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.61413(19) 0.15060(4) 0.11835(17) 0.0177(3) Uani 1 1 d . . . . .
C21 C 0.7065(2) 0.17492(4) 0.05883(18) 0.0183(4) Uani 1 1 d . . . . .
C22 C 0.6327(2) 0.19379(5) -0.06634(19) 0.0233(4) Uani 1 1 d . . . . .
H22A H 0.5236 0.1900 -0.1167 0.028 Uiso 1 1 calc R U . . .
C23 C 0.7168(2) 0.21800(5) -0.1181(2) 0.0284(4) Uani 1 1 d . . . . .
H23A H 0.6652 0.2307 -0.2036 0.034 Uiso 1 1 calc R U . . .
C24 C 0.8751(2) 0.22368(5) -0.0457(2) 0.0311(5) Uani 1 1 d . . . . .
H24A H 0.9327 0.2402 -0.0814 0.037 Uiso 1 1 calc R U . . .
C132 C 0.0500(2) 0.05384(6) 0.2079(2) 0.0325(5) Uani 1 1 d . . . . .
H13A H -0.0231 0.0559 0.2584 0.049 Uiso 1 1 calc R U . . .
H13B H 0.0204 0.0326 0.1444 0.049 Uiso 1 1 calc R U . . .
H13C H 0.1573 0.0504 0.2750 0.049 Uiso 1 1 calc R U . . .
C131 C 0.0426(2) 0.08907(5) 0.1238(2) 0.0260(4) Uani 1 1 d . . . . .
H13D H 0.0702 0.1105 0.1883 0.031 Uiso 1 1 calc R U . . .
H13E H -0.0666 0.0927 0.0578 0.031 Uiso 1 1 calc R U . . .
C111 C 0.1038(2) 0.05285(5) -0.10294(19) 0.0242(4) Uani 1 1 d . . . . .
H11A H 0.0934 0.0294 -0.0572 0.029 Uiso 1 1 calc R U . . .
H11B H -0.0022 0.0598 -0.1686 0.029 Uiso 1 1 calc R U . . .
C112 C 0.2115(2) 0.04649(6) -0.1858(2) 0.0337(5) Uani 1 1 d . . . . .
H11C H 0.1672 0.0270 -0.2553 0.050 Uiso 1 1 calc R U . . .
H11D H 0.2204 0.0694 -0.2335 0.050 Uiso 1 1 calc R U . . .
H11E H 0.3161 0.0390 -0.1220 0.050 Uiso 1 1 calc R U . . .
C4 C 0.47160(19) 0.13921(4) 0.26698(17) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.56266(19) 0.16455(4) 0.23332(17) 0.0174(4) Uani 1 1 d . . . . .
C31 C 0.62879(19) 0.19921(4) 0.31032(18) 0.0180(4) Uani 1 1 d . . . . .
C32 C 0.6355(2) 0.23270(4) 0.24429(19) 0.0207(4) Uani 1 1 d . . . . .
H32A H 0.5908 0.2343 0.1452 0.025 Uiso 1 1 calc R U . . .
C33 C 0.7062(2) 0.26360(5) 0.3211(2) 0.0243(4) Uani 1 1 d . . . . .
H33A H 0.7090 0.2861 0.2743 0.029 Uiso 1 1 calc R U . . .
C34 C 0.7726(2) 0.26198(5) 0.4651(2) 0.0267(4) Uani 1 1 d . . . . .
H34A H 0.8207 0.2833 0.5175 0.032 Uiso 1 1 calc R U . . .
C35 C 0.7686(2) 0.22908(5) 0.5325(2) 0.0266(4) Uani 1 1 d . . . . .
H35A H 0.8149 0.2277 0.6315 0.032 Uiso 1 1 calc R U . . .
C36 C 0.6972(2) 0.19821(5) 0.45617(19) 0.0227(4) Uani 1 1 d . . . . .
H36A H 0.6947 0.1758 0.5040 0.027 Uiso 1 1 calc R U . . .
C11 C 0.60446(19) 0.09144(4) -0.01783(18) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.6285(2) 0.05347(5) 0.00804(18) 0.0211(4) Uani 1 1 d . . . . .
H12A H 0.6243 0.0436 0.0926 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6581(2) 0.03001(5) -0.0861(2) 0.0259(4) Uani 1 1 d . . . . .
H13F H 0.6730 0.0044 -0.0659 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6663(2) 0.04366(5) -0.2096(2) 0.0275(4) Uani 1 1 d . . . . .
H14A H 0.6889 0.0276 -0.2733 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6411(2) 0.08090(5) -0.2390(2) 0.0276(4) Uani 1 1 d . . . . .
H15A H 0.6455 0.0905 -0.3238 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6092(2) 0.10434(5) -0.14515(18) 0.0240(4) Uani 1 1 d . . . . .
H16A H 0.5902 0.1298 -0.1679 0.029 Uiso 1 1 calc R U . . .
C25 C 0.9497(2) 0.20533(5) 0.0786(2) 0.0276(4) Uani 1 1 d . . . . .
H25A H 1.0588 0.2093 0.1285 0.033 Uiso 1 1 calc R U . . .
C26 C 0.8662(2) 0.18113(5) 0.13126(19) 0.0221(4) Uani 1 1 d . . . . .
H26A H 0.9183 0.1687 0.2173 0.027 Uiso 1 1 calc R U . . .
C41 C 0.3847(2) 0.14454(5) 0.36236(18) 0.0190(4) Uani 1 1 d . . . . .
C42 C 0.3585(2) 0.11477(5) 0.43801(19) 0.0258(4) Uani 1 1 d . . . . .
H42A H 0.4041 0.0914 0.4330 0.031 Uiso 1 1 calc R U . . .
C43 C 0.2673(2) 0.11864(6) 0.5202(2) 0.0342(5) Uani 1 1 d . . . . .
H43A H 0.2520 0.0980 0.5715 0.041 Uiso 1 1 calc R U . . .
C44 C 0.1986(2) 0.15206(6) 0.5285(2) 0.0355(5) Uani 1 1 d . . . . .
H44A H 0.1352 0.1545 0.5842 0.043 Uiso 1 1 calc R U . . .
C45 C 0.2228(2) 0.18188(5) 0.4549(2) 0.0341(5) Uani 1 1 d . . . . .
H45A H 0.1767 0.2051 0.4608 0.041 Uiso 1 1 calc R U . . .
C46 C 0.3140(2) 0.17821(5) 0.3725(2) 0.0258(4) Uani 1 1 d . . . . .
H46A H 0.3288 0.1990 0.3219 0.031 Uiso 1 1 calc R U . . .
C51 C 0.6112(2) 0.07398(4) 0.31415(17) 0.0177(4) Uani 1 1 d . . . . .
C52 C 0.7643(2) 0.08557(5) 0.39196(19) 0.0240(4) Uani 1 1 d . . . . .
H52A H 0.7964 0.1097 0.3776 0.029 Uiso 1 1 calc R U . . .
C53 C 0.8704(2) 0.06273(5) 0.48954(19) 0.0292(4) Uani 1 1 d . . . . .
H53A H 0.9736 0.0714 0.5406 0.035 Uiso 1 1 calc R U . . .
C54 C 0.8276(2) 0.02741(5) 0.5134(2) 0.0283(4) Uani 1 1 d . . . . .
H54A H 0.9009 0.0117 0.5794 0.034 Uiso 1 1 calc R U . . .
C55 C 0.6769(2) 0.01545(5) 0.43979(19) 0.0263(4) Uani 1 1 d . . . . .
H55A H 0.6454 -0.0087 0.4555 0.032 Uiso 1 1 calc R U . . .
C56 C 0.5707(2) 0.03844(5) 0.34286(18) 0.0217(4) Uani 1 1 d . . . . .
H56A H 0.4669 0.0297 0.2943 0.026 Uiso 1 1 calc R U . . .
C101 C 0.1664(2) 0.13167(5) -0.0564(2) 0.0286(4) Uani 1 1 d . . . . .
H10D H 0.1937 0.1514 0.0155 0.034 Uiso 1 1 calc R U . . .
H10E H 0.2477 0.1318 -0.0998 0.034 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
P1 O1 1.5281(12) . ?
P1 C111 1.7876(18) . ?
P1 C131 1.7887(18) . ?
P1 C101 1.7907(18) . ?
O1 B1 1.554(2) . ?
C102 C101 1.529(3) . ?
C102 H10A 0.9800 . ?
C102 H10B 0.9800 . ?
C102 H10C 0.9800 . ?
B1 C4 1.620(2) . ?
B1 C1 1.622(2) . ?
B1 C51 1.625(3) . ?
C1 C2 1.357(2) . ?
C1 C11 1.476(2) . ?
C2 C21 1.490(2) . ?
C2 C3 1.502(2) . ?
C21 C26 1.392(2) . ?
C21 C22 1.394(2) . ?
C22 C23 1.387(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.378(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.380(3) . ?
C24 H24A 0.9500 . ?
C132 C131 1.526(3) . ?
C132 H13A 0.9800 . ?
C132 H13B 0.9800 . ?
C132 H13C 0.9800 . ?
C131 H13D 0.9900 . ?
C131 H13E 0.9900 . ?
C111 C112 1.526(2) . ?
C111 H11A 0.9900 . ?
C111 H11B 0.9900 . ?
C112 H11C 0.9800 . ?
C112 H11D 0.9800 . ?
C112 H11E 0.9800 . ?
C4 C3 1.360(2) . ?
C4 C41 1.473(2) . ?
C3 C31 1.488(2) . ?
C31 C36 1.398(2) . ?
C31 C32 1.399(2) . ?
C32 C33 1.386(2) . ?
C32 H32A 0.9500 . ?
C33 C34 1.380(3) . ?
C33 H33A 0.9500 . ?
C34 C35 1.383(3) . ?
C34 H34A 0.9500 . ?
C35 C36 1.384(2) . ?
C35 H35A 0.9500 . ?
C36 H36A 0.9500 . ?
C11 C16 1.400(2) . ?
C11 C12 1.401(2) . ?
C12 C13 1.381(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13F 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.388(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C25 C26 1.388(2) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C41 C42 1.396(2) . ?
C41 C46 1.399(2) . ?
C42 C43 1.385(2) . ?
C42 H42A 0.9500 . ?
C43 C44 1.377(3) . ?
C43 H43A 0.9500 . ?
C44 C45 1.378(3) . ?
C44 H44A 0.9500 . ?
C45 C46 1.386(3) . ?
C45 H45A 0.9500 . ?
C46 H46A 0.9500 . ?
C51 C56 1.397(2) . ?
C51 C52 1.398(2) . ?
C52 C53 1.386(3) . ?
C52 H52A 0.9500 . ?
C53 C54 1.383(3) . ?
C53 H53A 0.9500 . ?
C54 C55 1.376(3) . ?
C54 H54A 0.9500 . ?
C55 C56 1.386(3) . ?
C55 H55A 0.9500 . ?
C56 H56A 0.9500 . ?
C101 H10D 0.9900 . ?
C101 H10E 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
O1 P1 C111 108.08(8) . . ?
O1 P1 C131 110.08(8) . . ?
C111 P1 C131 107.76(9) . . ?
O1 P1 C101 112.37(8) . . ?
C111 P1 C101 108.99(9) . . ?
C131 P1 C101 109.44(9) . . ?
P1 O1 B1 133.09(10) . . ?
C101 C102 H10A 109.5 . . ?
C101 C102 H10B 109.5 . . ?
H10A C102 H10B 109.5 . . ?
C101 C102 H10C 109.5 . . ?
H10A C102 H10C 109.5 . . ?
H10B C102 H10C 109.5 . . ?
O1 B1 C4 116.60(13) . . ?
O1 B1 C1 112.88(14) . . ?
C4 B1 C1 100.59(13) . . ?
O1 B1 C51 106.50(13) . . ?
C4 B1 C51 108.97(14) . . ?
C1 B1 C51 111.30(13) . . ?
C2 C1 C11 127.23(15) . . ?
C2 C1 B1 107.38(14) . . ?
C11 C1 B1 124.96(14) . . ?
C1 C2 C21 128.32(15) . . ?
C1 C2 C3 111.49(14) . . ?
C21 C2 C3 120.15(14) . . ?
C26 C21 C22 118.56(15) . . ?
C26 C21 C2 120.72(15) . . ?
C22 C21 C2 120.60(15) . . ?
C23 C22 C21 120.73(17) . . ?
C23 C22 H22A 119.6 . . ?
C21 C22 H22A 119.6 . . ?
C24 C23 C22 120.06(18) . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C23 C24 C25 119.90(17) . . ?
C23 C24 H24A 120.1 . . ?
C25 C24 H24A 120.1 . . ?
C131 C132 H13A 109.5 . . ?
C131 C132 H13B 109.5 . . ?
H13A C132 H13B 109.5 . . ?
C131 C132 H13C 109.5 . . ?
H13A C132 H13C 109.5 . . ?
H13B C132 H13C 109.5 . . ?
C132 C131 P1 112.87(13) . . ?
C132 C131 H13D 109.0 . . ?
P1 C131 H13D 109.0 . . ?
C132 C131 H13E 109.0 . . ?
P1 C131 H13E 109.0 . . ?
H13D C131 H13E 107.8 . . ?
C112 C111 P1 113.68(13) . . ?
C112 C111 H11A 108.8 . . ?
P1 C111 H11A 108.8 . . ?
C112 C111 H11B 108.8 . . ?
P1 C111 H11B 108.8 . . ?
H11A C111 H11B 107.7 . . ?
C111 C112 H11C 109.5 . . ?
C111 C112 H11D 109.5 . . ?
H11C C112 H11D 109.5 . . ?
C111 C112 H11E 109.5 . . ?
H11C C112 H11E 109.5 . . ?
H11D C112 H11E 109.5 . . ?
C3 C4 C41 126.88(15) . . ?
C3 C4 B1 107.00(14) . . ?
C41 C4 B1 125.83(14) . . ?
C4 C3 C31 126.91(15) . . ?
C4 C3 C2 111.18(14) . . ?
C31 C3 C2 121.22(14) . . ?
C36 C31 C32 117.34(15) . . ?
C36 C31 C3 119.02(15) . . ?
C32 C31 C3 123.52(15) . . ?
C33 C32 C31 121.03(17) . . ?
C33 C32 H32A 119.5 . . ?
C31 C32 H32A 119.5 . . ?
C34 C33 C32 120.61(16) . . ?
C34 C33 H33A 119.7 . . ?
C32 C33 H33A 119.7 . . ?
C33 C34 C35 119.32(17) . . ?
C33 C34 H34A 120.3 . . ?
C35 C34 H34A 120.3 . . ?
C34 C35 C36 120.26(18) . . ?
C34 C35 H35A 119.9 . . ?
C36 C35 H35A 119.9 . . ?
C35 C36 C31 121.44(16) . . ?
C35 C36 H36A 119.3 . . ?
C31 C36 H36A 119.3 . . ?
C16 C11 C12 116.61(15) . . ?
C16 C11 C1 124.21(15) . . ?
C12 C11 C1 119.14(15) . . ?
C13 C12 C11 121.75(16) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C12 C13 C14 120.44(17) . . ?
C12 C13 H13F 119.8 . . ?
C14 C13 H13F 119.8 . . ?
C15 C14 C13 119.20(16) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C14 C15 C16 120.28(17) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 121.69(17) . . ?
C15 C16 H16A 119.2 . . ?
C11 C16 H16A 119.2 . . ?
C24 C25 C26 120.34(18) . . ?
C24 C25 H25A 119.8 . . ?
C26 C25 H25A 119.8 . . ?
C25 C26 C21 120.40(17) . . ?
C25 C26 H26A 119.8 . . ?
C21 C26 H26A 119.8 . . ?
C42 C41 C46 117.11(15) . . ?
C42 C41 C4 120.41(15) . . ?
C46 C41 C4 122.25(15) . . ?
C43 C42 C41 121.23(17) . . ?
C43 C42 H42A 119.4 . . ?
C41 C42 H42A 119.4 . . ?
C44 C43 C42 120.64(18) . . ?
C44 C43 H43A 119.7 . . ?
C42 C43 H43A 119.7 . . ?
C43 C44 C45 119.26(17) . . ?
C43 C44 H44A 120.4 . . ?
C45 C44 H44A 120.4 . . ?
C44 C45 C46 120.41(18) . . ?
C44 C45 H45A 119.8 . . ?
C46 C45 H45A 119.8 . . ?
C45 C46 C41 121.35(17) . . ?
C45 C46 H46A 119.3 . . ?
C41 C46 H46A 119.3 . . ?
C56 C51 C52 116.08(16) . . ?
C56 C51 B1 122.93(15) . . ?
C52 C51 B1 120.97(15) . . ?
C53 C52 C51 121.76(17) . . ?
C53 C52 H52A 119.1 . . ?
C51 C52 H52A 119.1 . . ?
C54 C53 C52 120.70(18) . . ?
C54 C53 H53A 119.6 . . ?
C52 C53 H53A 119.6 . . ?
C55 C54 C53 118.80(17) . . ?
C55 C54 H54A 120.6 . . ?
C53 C54 H54A 120.6 . . ?
C54 C55 C56 120.35(17) . . ?
C54 C55 H55A 119.8 . . ?
C56 C55 H55A 119.8 . . ?
C55 C56 C51 122.27(17) . . ?
C55 C56 H56A 118.9 . . ?
C51 C56 H56A 118.9 . . ?
C102 C101 P1 114.17(13) . . ?
C102 C101 H10D 108.7 . . ?
P1 C101 H10D 108.7 . . ?
C102 C101 H10E 108.7 . . ?
P1 C101 H10E 108.7 . . ?
H10D C101 H10E 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C111 P1 O1 B1 139.88(14) . . . . ?
C131 P1 O1 B1 -102.67(15) . . . . ?
C101 P1 O1 B1 19.58(17) . . . . ?
P1 O1 B1 C4 44.2(2) . . . . ?
P1 O1 B1 C1 -71.53(18) . . . . ?
P1 O1 B1 C51 166.06(11) . . . . ?
O1 B1 C1 C2 136.76(14) . . . . ?
C4 B1 C1 C2 11.78(17) . . . . ?
C51 B1 C1 C2 -103.55(16) . . . . ?
O1 B1 C1 C11 -50.3(2) . . . . ?
C4 B1 C1 C11 -175.27(15) . . . . ?
C51 B1 C1 C11 69.4(2) . . . . ?
C11 C1 C2 C21 0.2(3) . . . . ?
B1 C1 C2 C21 172.98(16) . . . . ?
C11 C1 C2 C3 -177.58(15) . . . . ?
B1 C1 C2 C3 -4.83(19) . . . . ?
C1 C2 C21 C26 -100.9(2) . . . . ?
C3 C2 C21 C26 76.8(2) . . . . ?
C1 C2 C21 C22 83.2(2) . . . . ?
C3 C2 C21 C22 -99.13(19) . . . . ?
C26 C21 C22 C23 0.5(2) . . . . ?
C2 C21 C22 C23 176.47(16) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
O1 P1 C131 C132 -51.63(16) . . . . ?
C111 P1 C131 C132 66.02(16) . . . . ?
C101 P1 C131 C132 -175.60(14) . . . . ?
O1 P1 C111 C112 -56.23(15) . . . . ?
C131 P1 C111 C112 -175.16(14) . . . . ?
C101 P1 C111 C112 66.17(16) . . . . ?
O1 B1 C4 C3 -137.62(15) . . . . ?
C1 B1 C4 C3 -15.21(17) . . . . ?
C51 B1 C4 C3 101.85(16) . . . . ?
O1 B1 C4 C41 48.2(2) . . . . ?
C1 B1 C4 C41 170.65(15) . . . . ?
C51 B1 C4 C41 -72.3(2) . . . . ?
C41 C4 C3 C31 17.2(3) . . . . ?
B1 C4 C3 C31 -156.89(16) . . . . ?
C41 C4 C3 C2 -172.36(16) . . . . ?
B1 C4 C3 C2 13.58(19) . . . . ?
C1 C2 C3 C4 -5.9(2) . . . . ?
C21 C2 C3 C4 176.09(15) . . . . ?
C1 C2 C3 C31 165.20(15) . . . . ?
C21 C2 C3 C31 -12.8(2) . . . . ?
C4 C3 C31 C36 44.2(2) . . . . ?
C2 C3 C31 C36 -125.41(17) . . . . ?
C4 C3 C31 C32 -139.95(18) . . . . ?
C2 C3 C31 C32 50.5(2) . . . . ?
C36 C31 C32 C33 -0.5(2) . . . . ?
C3 C31 C32 C33 -176.41(15) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C34 C35 C36 C31 0.4(3) . . . . ?
C32 C31 C36 C35 0.1(2) . . . . ?
C3 C31 C36 C35 176.22(16) . . . . ?
C2 C1 C11 C16 -36.2(3) . . . . ?
B1 C1 C11 C16 152.26(17) . . . . ?
C2 C1 C11 C12 146.31(18) . . . . ?
B1 C1 C11 C12 -25.2(2) . . . . ?
C16 C11 C12 C13 1.1(3) . . . . ?
C1 C11 C12 C13 178.79(16) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C11 1.2(3) . . . . ?
C12 C11 C16 C15 -2.0(3) . . . . ?
C1 C11 C16 C15 -179.52(17) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C24 C25 C26 C21 0.4(3) . . . . ?
C22 C21 C26 C25 -0.7(2) . . . . ?
C2 C21 C26 C25 -176.65(16) . . . . ?
C3 C4 C41 C42 -149.99(18) . . . . ?
B1 C4 C41 C42 23.0(3) . . . . ?
C3 C4 C41 C46 35.6(3) . . . . ?
B1 C4 C41 C46 -151.46(17) . . . . ?
C46 C41 C42 C43 -0.5(3) . . . . ?
C4 C41 C42 C43 -175.20(17) . . . . ?
C41 C42 C43 C44 0.6(3) . . . . ?
C42 C43 C44 C45 -0.7(3) . . . . ?
C43 C44 C45 C46 0.6(3) . . . . ?
C44 C45 C46 C41 -0.5(3) . . . . ?
C42 C41 C46 C45 0.4(3) . . . . ?
C4 C41 C46 C45 175.05(18) . . . . ?
O1 B1 C51 C56 -2.6(2) . . . . ?
C4 B1 C51 C56 123.96(16) . . . . ?
C1 B1 C51 C56 -126.01(16) . . . . ?
O1 B1 C51 C52 175.98(14) . . . . ?
C4 B1 C51 C52 -57.46(19) . . . . ?
C1 B1 C51 C52 52.6(2) . . . . ?
C56 C51 C52 C53 1.4(2) . . . . ?
B1 C51 C52 C53 -177.27(16) . . . . ?
C51 C52 C53 C54 -0.1(3) . . . . ?
C52 C53 C54 C55 -0.9(3) . . . . ?
C53 C54 C55 C56 0.5(3) . . . . ?
C54 C55 C56 C51 0.9(3) . . . . ?
C52 C51 C56 C55 -1.8(2) . . . . ?
B1 C51 C56 C55 176.85(16) . . . . ?
O1 P1 C101 C102 172.32(13) . . . . ?
C111 P1 C101 C102 52.54(17) . . . . ?
C131 P1 C101 C102 -65.07(17) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3

_chemical_properties_physical    Air-sensitive,Moisture-sensitive
####################################################################### 
# 
# 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_3PhEt3PO
_database_code_depnum_ccdc_archive 'CCDC 1819494'
_audit_update_record             
;
2018-01-25 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;

_vrf_PLAT340_ALERT_3_C           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00573 Ang.    

RESPONSE: This error is a result of the data obtained for the structure.  
;

_vrf_PLAT042_ALERT_1_G           
;
PROBLEM:   Calc. and Reported MoietyFormula Strings  Differ     Please Check 
         
RESPONSE: Platon ADDSYM, NEWSYM, and CALCALL do not find a higher symmetry unit cell, so two molecules exist in the asymmetric unit.
;

_vrf_PLAT045_ALERT_1_G           
;
PROBLEM:  Calculated and Reported Z Differ by a Factor ...       2.00 Check    

RESPONSE: Platon ADDSYM, NEWSYM, and CALCALL do not find a higher symmetry unit cell, so two molecules exist in the asymmetric unit. 
;

_vrf_PLAT395_ALERT_2_G           
;
PROBLEM:  Deviating  X-O-Y  Angle From 120 for  O1/O2          135.7/135.0 Degree  
         
RESPONSE: The deviation is due to the nature of the adduct bond between the boron atom and oxygen atom of the molecule.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            3PhEt3PO
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H56 B2 O2 P2'
_chemical_formula_sum            'C48 H56 B2 O2 P2'
_chemical_formula_weight         748.48

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   9.8145(9)
_cell_length_b                   15.5763(15)
_cell_length_c                   13.7943(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.023(3)
_cell_angle_gamma                90
_cell_volume                     2108.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9834
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.98

_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             802
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.168
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SABADs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53004
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.453
_diffrn_reflns_theta_max         27.104
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9321
_reflns_number_gt                7424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.998
_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.
 
 _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 (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)+(0.0518P)²+0.5872P] 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 3157 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9321
_refine_ls_number_parameters     493
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
P1 P 0.73350(9) 0.54376(6) 0.98401(7) 0.0260(2) Uani 1 1 d . . . . .
O1 O 0.8489(2) 0.49311(15) 0.93733(18) 0.0260(6) Uani 1 1 d . . . . .
C1 C 1.1428(5) 0.2639(3) 0.7786(3) 0.0398(10) Uani 1 1 d . . . . .
H1 H 1.1788 0.2109 0.7560 0.048 Uiso 1 1 calc R U . . .
C2 C 1.2282(4) 0.3274(3) 0.8103(3) 0.0381(10) Uani 1 1 d . . . . .
H11 H 1.3239 0.3181 0.8107 0.046 Uiso 1 1 calc R U . . .
C3 C 1.1760(4) 0.4054(2) 0.8420(3) 0.0323(9) Uani 1 1 d . . . . .
H12 H 1.2373 0.4487 0.8634 0.039 Uiso 1 1 calc R U . . .
C4 C 1.0361(4) 0.4224(2) 0.8434(3) 0.0252(8) Uani 1 1 d . . . . .
B2 B 0.9731(4) 0.5149(3) 0.8708(3) 0.0237(9) Uani 1 1 d . . . . .
C6 C 0.6931(4) 0.4912(3) 1.0952(3) 0.0378(10) Uani 1 1 d . . . . .
H23 H 0.6366 0.5298 1.1355 0.045 Uiso 1 1 calc R U . . .
H24 H 0.6389 0.4390 1.0812 0.045 Uiso 1 1 calc R U . . .
C7 C 0.8203(5) 0.4659(3) 1.1517(3) 0.0485(12) Uani 1 1 d . . . . .
H2 H 0.8761 0.5171 1.1634 0.073 Uiso 1 1 calc R U . . .
H21 H 0.8728 0.4240 1.1142 0.073 Uiso 1 1 calc R U . . .
H22 H 0.7936 0.4405 1.2138 0.073 Uiso 1 1 calc R U . . .
C8 C 0.5558(4) 0.4528(3) 0.8676(3) 0.0438(11) Uani 1 1 d . . . . .
H3 H 0.4767 0.4553 0.8243 0.066 Uiso 1 1 calc R U . . .
H27 H 0.5364 0.4139 0.9216 0.066 Uiso 1 1 calc R U . . .
H28 H 0.6351 0.4318 0.8316 0.066 Uiso 1 1 calc R U . . .
C9 C 0.5854(4) 0.5416(3) 0.9064(3) 0.0380(10) Uani 1 1 d . . . . .
H25 H 0.5054 0.5622 0.9434 0.046 Uiso 1 1 calc R U . . .
H26 H 0.5999 0.5813 0.8514 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7747(4) 0.6536(2) 1.0068(3) 0.0337(9) Uani 1 1 d . . . . .
H4 H 0.8408 0.6564 1.0610 0.040 Uiso 1 1 calc R U . . .
H5 H 0.8197 0.6778 0.9486 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6518(4) 0.7090(3) 1.0319(3) 0.0393(10) Uani 1 1 d . . . . .
H6 H 0.6008 0.6822 1.0849 0.059 Uiso 1 1 calc R U . . .
H7 H 0.5927 0.7143 0.9749 0.059 Uiso 1 1 calc R U . . .
H8 H 0.6826 0.7661 1.0521 0.059 Uiso 1 1 calc R U . . .
C12 C 1.0026(5) 0.2776(2) 0.7797(3) 0.0390(10) Uani 1 1 d . . . . .
H10 H 0.9418 0.2337 0.7594 0.047 Uiso 1 1 calc R U . . .
C13 C 0.9533(4) 0.3556(2) 0.8108(3) 0.0331(9) Uani 1 1 d . . . . .
H9 H 0.8575 0.3645 0.8100 0.040 Uiso 1 1 calc R U . . .
C14 C 1.0766(3) 0.5826(2) 0.9200(3) 0.0263(8) Uani 1 1 d . . . . .
C15 C 1.0991(4) 0.6514(2) 0.8557(3) 0.0288(9) Uani 1 1 d . . . . .
C16 C 1.0152(3) 0.6421(2) 0.7680(3) 0.0251(8) Uani 1 1 d . . . . .
C17 C 0.9323(3) 0.5681(2) 0.7737(3) 0.0224(8) Uani 1 1 d . . . . .
C18 C 0.8472(4) 0.5504(2) 0.6959(3) 0.0281(8) Uani 1 1 d . . . . .
H16 H 0.7898 0.5014 0.6984 0.034 Uiso 1 1 calc R U . . .
C19 C 0.8439(4) 0.6026(2) 0.6146(3) 0.0340(9) Uani 1 1 d . . . . .
H15 H 0.7839 0.5897 0.5626 0.041 Uiso 1 1 calc R U . . .
C20 C 0.9287(4) 0.6741(3) 0.6095(3) 0.0373(10) Uani 1 1 d . . . . .
H14 H 0.9285 0.7090 0.5531 0.045 Uiso 1 1 calc R U . . .
C21 C 1.0134(4) 0.6943(2) 0.6865(3) 0.0332(9) Uani 1 1 d . . . . .
H13 H 1.0699 0.7438 0.6835 0.040 Uiso 1 1 calc R U . . .
C22 C 1.1906(4) 0.7170(3) 0.8783(3) 0.0386(10) Uani 1 1 d . . . . .
H20 H 1.2045 0.7631 0.8342 0.046 Uiso 1 1 calc R U . . .
C23 C 1.2606(4) 0.7147(3) 0.9649(4) 0.0437(12) Uani 1 1 d . . . . .
H19 H 1.3239 0.7588 0.9803 0.052 Uiso 1 1 calc R U . . .
C24 C 1.2386(4) 0.6483(3) 1.0293(3) 0.0413(11) Uani 1 1 d . . . . .
H18 H 1.2860 0.6472 1.0894 0.050 Uiso 1 1 calc R U . . .
C25 C 1.1478(4) 0.5830(3) 1.0068(3) 0.0333(9) Uani 1 1 d . . . . .
H17 H 1.1342 0.5376 1.0518 0.040 Uiso 1 1 calc R U . . .
P2 P 0.76881(9) 0.96868(6) 0.49989(7) 0.0252(2) Uani 1 1 d . . . . .
O2 O 0.8821(2) 1.01459(15) 0.44501(19) 0.0271(6) Uani 1 1 d . . . . .
C26 C 1.2055(4) 1.2281(2) 0.2899(3) 0.0338(9) Uani 1 1 d . . . . .
H29 H 1.2447 1.2785 0.2629 0.041 Uiso 1 1 calc R U . . .
C27 C 1.2867(4) 1.1671(2) 0.3338(3) 0.0357(9) Uani 1 1 d . . . . .
H49 H 1.3822 1.1762 0.3387 0.043 Uiso 1 1 calc R U . . .
C28 C 1.2296(4) 1.0924(2) 0.3710(3) 0.0295(8) Uani 1 1 d . . . . .
H50 H 1.2873 1.0511 0.4009 0.035 Uiso 1 1 calc R U . . .
C29 C 1.0902(4) 1.0762(2) 0.3658(2) 0.0235(8) Uani 1 1 d . . . . .
C30 C 1.0024(3) 0.9197(2) 0.3107(3) 0.0242(8) Uani 1 1 d . . . . .
C31 C 1.0764(4) 0.8446(2) 0.3295(3) 0.0255(8) Uani 1 1 d . . . . .
C32 C 1.0827(4) 0.7783(2) 0.2618(3) 0.0335(9) Uani 1 1 d . . . . .
H42 H 1.1344 0.7281 0.2751 0.040 Uiso 1 1 calc R U . . .
C33 C 1.0128(4) 0.7863(3) 0.1750(3) 0.0377(10) Uani 1 1 d . . . . .
H30 H 1.0159 0.7412 0.1287 0.045 Uiso 1 1 calc R U . . .
C34 C 0.8253(5) 1.0718(3) 0.6585(3) 0.0496(12) Uani 1 1 d . . . . .
H31 H 0.7514 1.1109 0.6402 0.074 Uiso 1 1 calc R U . . .
H32 H 0.9095 1.0893 0.6258 0.074 Uiso 1 1 calc R U . . .
H33 H 0.8387 1.0739 0.7289 0.074 Uiso 1 1 calc R U . . .
C35 C 0.6117(4) 1.0174(3) 0.4617(3) 0.0353(10) Uani 1 1 d . . . . .
H38 H 0.5348 0.9913 0.4977 0.042 Uiso 1 1 calc R U . . .
H39 H 0.6137 1.0795 0.4770 0.042 Uiso 1 1 calc R U . . .
C36 C 0.5896(5) 1.0053(4) 0.3530(3) 0.0521(13) Uani 1 1 d . . . . .
H35 H 0.5110 1.0394 0.3321 0.078 Uiso 1 1 calc R U . . .
H36 H 0.5726 0.9445 0.3393 0.078 Uiso 1 1 calc R U . . .
H37 H 0.6710 1.0241 0.3179 0.078 Uiso 1 1 calc R U . . .
C37 C 0.9386(4) 0.8600(3) 0.1555(3) 0.0356(10) Uani 1 1 d . . . . .
H40 H 0.8907 0.8653 0.0959 0.043 Uiso 1 1 calc R U . . .
C38 C 0.9343(4) 0.9263(2) 0.2233(3) 0.0296(8) Uani 1 1 d . . . . .
H41 H 0.8838 0.9768 0.2092 0.036 Uiso 1 1 calc R U . . .
C39 C 1.1432(4) 0.8486(2) 0.4255(3) 0.0262(8) Uani 1 1 d . . . . .
C40 C 1.2246(4) 0.7872(2) 0.4691(3) 0.0337(10) Uani 1 1 d . . . . .
H46 H 1.2437 0.7348 0.4367 0.040 Uiso 1 1 calc R U . . .
C41 C 1.2776(4) 0.8027(3) 0.5597(3) 0.0370(10) Uani 1 1 d . . . . .
H45 H 1.3333 0.7609 0.5903 0.044 Uiso 1 1 calc R U . . .
C42 C 1.2496(4) 0.8791(3) 0.6061(3) 0.0392(10) Uani 1 1 d . . . . .
H44 H 1.2867 0.8895 0.6686 0.047 Uiso 1 1 calc R U . . .
C43 C 1.1681(4) 0.9408(2) 0.5629(3) 0.0316(9) Uani 1 1 d . . . . .
H43 H 1.1499 0.9929 0.5962 0.038 Uiso 1 1 calc R U . . .
C44 C 1.1128(3) 0.9274(2) 0.4714(3) 0.0257(8) Uani 1 1 d . . . . .
C45 C 1.0657(4) 1.2147(2) 0.2856(3) 0.0332(9) Uani 1 1 d . . . . .
H48 H 1.0081 1.2568 0.2572 0.040 Uiso 1 1 calc R U . . .
C46 C 1.0107(4) 1.1402(2) 0.3227(3) 0.0275(8) Uani 1 1 d . . . . .
H47 H 0.9150 1.1320 0.3188 0.033 Uiso 1 1 calc R U . . .
C47 C 0.7636(4) 0.8564(2) 0.4752(3) 0.0332(9) Uani 1 1 d . . . . .
H54 H 0.7628 0.8480 0.4041 0.040 Uiso 1 1 calc R U . . .
H55 H 0.8478 0.8298 0.5007 0.040 Uiso 1 1 calc R U . . .
C48 C 0.6410(4) 0.8098(3) 0.5186(3) 0.0411(10) Uani 1 1 d . . . . .
H51 H 0.5570 0.8323 0.4898 0.062 Uiso 1 1 calc R U . . .
H52 H 0.6391 0.8189 0.5889 0.062 Uiso 1 1 calc R U . . .
H53 H 0.6482 0.7482 0.5049 0.062 Uiso 1 1 calc R U . . .
B1 B 1.0222(4) 0.9869(3) 0.4004(3) 0.0257(9) Uani 1 1 d . . . . .
C101 C 0.7890(4) 0.9819(3) 0.6287(3) 0.0406(10) Uani 1 1 d . . . . .
H10A H 0.7030 0.9652 0.6611 0.049 Uiso 1 1 calc R U . . .
H10B H 0.8612 0.9424 0.6516 0.049 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
P1 O1 1.523(2) . ?
P1 C6 1.783(4) . ?
P1 C10 1.787(4) . ?
P1 C9 1.805(4) . ?
O1 B2 1.563(4) . ?
C1 C2 1.369(6) . ?
C1 C12 1.392(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(5) . ?
C2 H11 0.9500 . ?
C3 C4 1.398(5) . ?
C3 H12 0.9500 . ?
C4 C13 1.395(5) . ?
C4 B2 1.613(5) . ?
B2 C14 1.614(5) . ?
B2 C17 1.625(5) . ?
C6 C7 1.523(6) . ?
C6 H23 0.9900 . ?
C6 H24 0.9900 . ?
C7 H2 0.9800 . ?
C7 H21 0.9800 . ?
C7 H22 0.9800 . ?
C8 C9 1.511(6) . ?
C8 H3 0.9800 . ?
C8 H27 0.9800 . ?
C8 H28 0.9800 . ?
C9 H25 0.9900 . ?
C9 H26 0.9900 . ?
C10 C11 1.523(5) . ?
C10 H4 0.9900 . ?
C10 H5 0.9900 . ?
C11 H6 0.9800 . ?
C11 H7 0.9800 . ?
C11 H8 0.9800 . ?
C12 C13 1.377(5) . ?
C12 H10 0.9500 . ?
C13 H9 0.9500 . ?
C14 C25 1.386(6) . ?
C14 C15 1.408(5) . ?
C15 C22 1.396(5) . ?
C15 C16 1.470(6) . ?
C16 C21 1.388(5) . ?
C16 C17 1.413(5) . ?
C17 C18 1.388(5) . ?
C18 C19 1.385(5) . ?
C18 H16 0.9500 . ?
C19 C20 1.391(6) . ?
C19 H15 0.9500 . ?
C20 C21 1.384(6) . ?
C20 H14 0.9500 . ?
C21 H13 0.9500 . ?
C22 C23 1.379(6) . ?
C22 H20 0.9500 . ?
C23 C24 1.381(6) . ?
C23 H19 0.9500 . ?
C24 C25 1.387(6) . ?
C24 H18 0.9500 . ?
C25 H17 0.9500 . ?
P2 O2 1.524(2) . ?
P2 C47 1.782(4) . ?
P2 C35 1.798(4) . ?
P2 C101 1.800(4) . ?
O2 B1 1.567(4) . ?
C26 C27 1.380(6) . ?
C26 C45 1.389(6) . ?
C26 H29 0.9500 . ?
C27 C28 1.390(5) . ?
C27 H49 0.9500 . ?
C28 C29 1.393(5) . ?
C28 H50 0.9500 . ?
C29 C46 1.399(5) . ?
C29 B1 1.615(5) . ?
C30 C38 1.382(5) . ?
C30 C31 1.401(5) . ?
C30 B1 1.633(5) . ?
C31 C32 1.393(5) . ?
C31 C39 1.479(5) . ?
C32 C33 1.386(6) . ?
C32 H42 0.9500 . ?
C33 C37 1.385(6) . ?
C33 H30 0.9500 . ?
C34 C101 1.503(6) . ?
C34 H31 0.9800 . ?
C34 H32 0.9800 . ?
C34 H33 0.9800 . ?
C35 C36 1.527(6) . ?
C35 H38 0.9900 . ?
C35 H39 0.9900 . ?
C36 H35 0.9800 . ?
C36 H36 0.9800 . ?
C36 H37 0.9800 . ?
C37 C38 1.395(5) . ?
C37 H40 0.9500 . ?
C38 H41 0.9500 . ?
C39 C40 1.384(5) . ?
C39 C44 1.413(5) . ?
C40 C41 1.376(6) . ?
C40 H46 0.9500 . ?
C41 C42 1.378(6) . ?
C41 H45 0.9500 . ?
C42 C43 1.385(6) . ?
C42 H44 0.9500 . ?
C43 C44 1.389(5) . ?
C43 H43 0.9500 . ?
C44 B1 1.614(6) . ?
C45 C46 1.377(5) . ?
C45 H48 0.9500 . ?
C46 H47 0.9500 . ?
C47 C48 1.527(5) . ?
C47 H54 0.9900 . ?
C47 H55 0.9900 . ?
C48 H51 0.9800 . ?
C48 H52 0.9800 . ?
C48 H53 0.9800 . ?
C101 H10A 0.9900 . ?
C101 H10B 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
O1 P1 C6 106.93(18) . . ?
O1 P1 C10 113.71(16) . . ?
C6 P1 C10 109.8(2) . . ?
O1 P1 C9 109.77(17) . . ?
C6 P1 C9 108.8(2) . . ?
C10 P1 C9 107.7(2) . . ?
P1 O1 B2 135.7(2) . . ?
C2 C1 C12 119.4(4) . . ?
C2 C1 H1 120.3 . . ?
C12 C1 H1 120.3 . . ?
C1 C2 C3 120.4(4) . . ?
C1 C2 H11 119.8 . . ?
C3 C2 H11 119.8 . . ?
C2 C3 C4 122.2(4) . . ?
C2 C3 H12 118.9 . . ?
C4 C3 H12 118.9 . . ?
C13 C4 C3 115.3(3) . . ?
C13 C4 B2 121.2(3) . . ?
C3 C4 B2 123.3(3) . . ?
O1 B2 C4 104.1(3) . . ?
O1 B2 C14 112.7(3) . . ?
C4 B2 C14 116.2(3) . . ?
O1 B2 C17 113.7(3) . . ?
C4 B2 C17 110.9(3) . . ?
C14 B2 C17 99.7(3) . . ?
C7 C6 P1 112.1(3) . . ?
C7 C6 H23 109.2 . . ?
P1 C6 H23 109.2 . . ?
C7 C6 H24 109.2 . . ?
P1 C6 H24 109.2 . . ?
H23 C6 H24 107.9 . . ?
C6 C7 H2 109.5 . . ?
C6 C7 H21 109.5 . . ?
H2 C7 H21 109.5 . . ?
C6 C7 H22 109.5 . . ?
H2 C7 H22 109.5 . . ?
H21 C7 H22 109.5 . . ?
C9 C8 H3 109.5 . . ?
C9 C8 H27 109.5 . . ?
H3 C8 H27 109.5 . . ?
C9 C8 H28 109.5 . . ?
H3 C8 H28 109.5 . . ?
H27 C8 H28 109.5 . . ?
C8 C9 P1 112.5(3) . . ?
C8 C9 H25 109.1 . . ?
P1 C9 H25 109.1 . . ?
C8 C9 H26 109.1 . . ?
P1 C9 H26 109.1 . . ?
H25 C9 H26 107.8 . . ?
C11 C10 P1 113.8(3) . . ?
C11 C10 H4 108.8 . . ?
P1 C10 H4 108.8 . . ?
C11 C10 H5 108.8 . . ?
P1 C10 H5 108.8 . . ?
H4 C10 H5 107.7 . . ?
C10 C11 H6 109.5 . . ?
C10 C11 H7 109.5 . . ?
H6 C11 H7 109.5 . . ?
C10 C11 H8 109.5 . . ?
H6 C11 H8 109.5 . . ?
H7 C11 H8 109.5 . . ?
C13 C12 C1 119.1(4) . . ?
C13 C12 H10 120.4 . . ?
C1 C12 H10 120.4 . . ?
C12 C13 C4 123.6(4) . . ?
C12 C13 H9 118.2 . . ?
C4 C13 H9 118.2 . . ?
C25 C14 C15 117.5(3) . . ?
C25 C14 B2 133.1(3) . . ?
C15 C14 B2 109.3(3) . . ?
C22 C15 C14 121.2(4) . . ?
C22 C15 C16 128.0(4) . . ?
C14 C15 C16 110.8(3) . . ?
C21 C16 C17 121.1(4) . . ?
C21 C16 C15 128.0(3) . . ?
C17 C16 C15 110.9(3) . . ?
C18 C17 C16 117.7(3) . . ?
C18 C17 B2 133.2(3) . . ?
C16 C17 B2 108.7(3) . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H16 119.2 . . ?
C17 C18 H16 119.2 . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 H15 120.1 . . ?
C20 C19 H15 120.1 . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H14 119.9 . . ?
C19 C20 H14 119.9 . . ?
C20 C21 C16 119.7(4) . . ?
C20 C21 H13 120.2 . . ?
C16 C21 H13 120.2 . . ?
C23 C22 C15 119.6(4) . . ?
C23 C22 H20 120.2 . . ?
C15 C22 H20 120.2 . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 H19 120.0 . . ?
C24 C23 H19 120.0 . . ?
C23 C24 C25 120.4(4) . . ?
C23 C24 H18 119.8 . . ?
C25 C24 H18 119.8 . . ?
C14 C25 C24 121.3(4) . . ?
C14 C25 H17 119.3 . . ?
C24 C25 H17 119.3 . . ?
O2 P2 C47 112.75(16) . . ?
O2 P2 C35 106.41(16) . . ?
C47 P2 C35 109.5(2) . . ?
O2 P2 C101 110.91(18) . . ?
C47 P2 C101 107.7(2) . . ?
C35 P2 C101 109.6(2) . . ?
P2 O2 B1 134.9(2) . . ?
C27 C26 C45 119.0(3) . . ?
C27 C26 H29 120.5 . . ?
C45 C26 H29 120.5 . . ?
C26 C27 C28 120.4(4) . . ?
C26 C27 H49 119.8 . . ?
C28 C27 H49 119.8 . . ?
C27 C28 C29 121.9(4) . . ?
C27 C28 H50 119.1 . . ?
C29 C28 H50 119.1 . . ?
C28 C29 C46 116.1(3) . . ?
C28 C29 B1 123.1(3) . . ?
C46 C29 B1 120.6(3) . . ?
C38 C30 C31 118.3(3) . . ?
C38 C30 B1 132.1(3) . . ?
C31 C30 B1 109.5(3) . . ?
C32 C31 C30 121.2(4) . . ?
C32 C31 C39 127.7(4) . . ?
C30 C31 C39 111.1(3) . . ?
C33 C32 C31 119.3(4) . . ?
C33 C32 H42 120.3 . . ?
C31 C32 H42 120.3 . . ?
C37 C33 C32 120.2(4) . . ?
C37 C33 H30 119.9 . . ?
C32 C33 H30 119.9 . . ?
C101 C34 H31 109.5 . . ?
C101 C34 H32 109.5 . . ?
H31 C34 H32 109.5 . . ?
C101 C34 H33 109.5 . . ?
H31 C34 H33 109.5 . . ?
H32 C34 H33 109.5 . . ?
C36 C35 P2 110.9(3) . . ?
C36 C35 H38 109.5 . . ?
P2 C35 H38 109.5 . . ?
C36 C35 H39 109.5 . . ?
P2 C35 H39 109.5 . . ?
H38 C35 H39 108.1 . . ?
C35 C36 H35 109.5 . . ?
C35 C36 H36 109.5 . . ?
H35 C36 H36 109.5 . . ?
C35 C36 H37 109.5 . . ?
H35 C36 H37 109.5 . . ?
H36 C36 H37 109.5 . . ?
C33 C37 C38 120.0(4) . . ?
C33 C37 H40 120.0 . . ?
C38 C37 H40 120.0 . . ?
C30 C38 C37 121.0(4) . . ?
C30 C38 H41 119.5 . . ?
C37 C38 H41 119.5 . . ?
C40 C39 C44 121.8(4) . . ?
C40 C39 C31 128.0(4) . . ?
C44 C39 C31 110.2(3) . . ?
C41 C40 C39 119.4(4) . . ?
C41 C40 H46 120.3 . . ?
C39 C40 H46 120.3 . . ?
C40 C41 C42 119.9(4) . . ?
C40 C41 H45 120.1 . . ?
C42 C41 H45 120.1 . . ?
C41 C42 C43 121.0(4) . . ?
C41 C42 H44 119.5 . . ?
C43 C42 H44 119.5 . . ?
C42 C43 C44 120.8(4) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 H43 119.6 . . ?
C43 C44 C39 117.1(3) . . ?
C43 C44 B1 132.8(3) . . ?
C39 C44 B1 110.0(3) . . ?
C46 C45 C26 119.8(4) . . ?
C46 C45 H48 120.1 . . ?
C26 C45 H48 120.1 . . ?
C45 C46 C29 122.7(3) . . ?
C45 C46 H47 118.7 . . ?
C29 C46 H47 118.7 . . ?
C48 C47 P2 114.5(3) . . ?
C48 C47 H54 108.6 . . ?
P2 C47 H54 108.6 . . ?
C48 C47 H55 108.6 . . ?
P2 C47 H55 108.6 . . ?
H54 C47 H55 107.6 . . ?
C47 C48 H51 109.5 . . ?
C47 C48 H52 109.5 . . ?
H51 C48 H52 109.5 . . ?
C47 C48 H53 109.5 . . ?
H51 C48 H53 109.5 . . ?
H52 C48 H53 109.5 . . ?
O2 B1 C44 113.8(3) . . ?
O2 B1 C29 104.0(3) . . ?
C44 B1 C29 116.5(3) . . ?
O2 B1 C30 111.7(3) . . ?
C44 B1 C30 99.0(3) . . ?
C29 B1 C30 112.2(3) . . ?
C34 C101 P2 113.7(3) . . ?
C34 C101 H10A 108.8 . . ?
P2 C101 H10A 108.8 . . ?
C34 C101 H10B 108.8 . . ?
P2 C101 H10B 108.8 . . ?
H10A C101 H10B 107.7 . . ?

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
C6 P1 O1 B2 -148.5(3) . . . . ?
C10 P1 O1 B2 -27.1(4) . . . . ?
C9 P1 O1 B2 93.7(3) . . . . ?
C12 C1 C2 C3 -1.0(6) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C13 0.0(6) . . . . ?
C2 C3 C4 B2 -174.5(4) . . . . ?
P1 O1 B2 C4 -173.5(3) . . . . ?
P1 O1 B2 C14 59.7(4) . . . . ?
P1 O1 B2 C17 -52.8(5) . . . . ?
C13 C4 B2 O1 48.1(4) . . . . ?
C3 C4 B2 O1 -137.7(3) . . . . ?
C13 C4 B2 C14 172.6(3) . . . . ?
C3 C4 B2 C14 -13.1(5) . . . . ?
C13 C4 B2 C17 -74.5(4) . . . . ?
C3 C4 B2 C17 99.7(4) . . . . ?
O1 P1 C6 C7 44.1(4) . . . . ?
C10 P1 C6 C7 -79.7(4) . . . . ?
C9 P1 C6 C7 162.6(3) . . . . ?
O1 P1 C9 C8 45.4(3) . . . . ?
C6 P1 C9 C8 -71.3(3) . . . . ?
C10 P1 C9 C8 169.7(3) . . . . ?
O1 P1 C10 C11 167.0(3) . . . . ?
C6 P1 C10 C11 -73.2(4) . . . . ?
C9 P1 C10 C11 45.1(4) . . . . ?
C2 C1 C12 C13 1.4(6) . . . . ?
C1 C12 C13 C4 -1.2(6) . . . . ?
C3 C4 C13 C12 0.5(6) . . . . ?
B2 C4 C13 C12 175.1(4) . . . . ?
O1 B2 C14 C25 56.1(5) . . . . ?
C4 B2 C14 C25 -63.9(5) . . . . ?
C17 B2 C14 C25 177.0(4) . . . . ?
O1 B2 C14 C15 -127.5(3) . . . . ?
C4 B2 C14 C15 112.5(3) . . . . ?
C17 B2 C14 C15 -6.6(3) . . . . ?
C25 C14 C15 C22 0.5(5) . . . . ?
B2 C14 C15 C22 -176.6(3) . . . . ?
C25 C14 C15 C16 -179.4(3) . . . . ?
B2 C14 C15 C16 3.6(4) . . . . ?
C22 C15 C16 C21 3.4(6) . . . . ?
C14 C15 C16 C21 -176.8(3) . . . . ?
C22 C15 C16 C17 -178.1(3) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C21 C16 C17 C18 -1.2(5) . . . . ?
C15 C16 C17 C18 -179.9(3) . . . . ?
C21 C16 C17 B2 172.5(3) . . . . ?
C15 C16 C17 B2 -6.1(4) . . . . ?
O1 B2 C17 C18 -59.9(5) . . . . ?
C4 B2 C17 C18 56.9(5) . . . . ?
C14 B2 C17 C18 179.9(3) . . . . ?
O1 B2 C17 C16 127.7(3) . . . . ?
C4 B2 C17 C16 -115.4(3) . . . . ?
C14 B2 C17 C16 7.5(3) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
B2 C17 C18 C19 -171.2(3) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C18 C19 C20 C21 -1.8(5) . . . . ?
C19 C20 C21 C16 1.3(5) . . . . ?
C17 C16 C21 C20 0.2(5) . . . . ?
C15 C16 C21 C20 178.6(3) . . . . ?
C14 C15 C22 C23 0.2(5) . . . . ?
C16 C15 C22 C23 179.9(4) . . . . ?
C15 C22 C23 C24 -0.9(6) . . . . ?
C22 C23 C24 C25 0.9(6) . . . . ?
C15 C14 C25 C24 -0.4(5) . . . . ?
B2 C14 C25 C24 175.8(4) . . . . ?
C23 C24 C25 C14 -0.3(6) . . . . ?
C47 P2 O2 B1 -24.7(4) . . . . ?
C35 P2 O2 B1 -144.8(3) . . . . ?
C101 P2 O2 B1 96.1(4) . . . . ?
C45 C26 C27 C28 1.6(6) . . . . ?
C26 C27 C28 C29 -0.1(6) . . . . ?
C27 C28 C29 C46 -1.2(5) . . . . ?
C27 C28 C29 B1 174.9(3) . . . . ?
C38 C30 C31 C32 0.5(5) . . . . ?
B1 C30 C31 C32 -176.6(3) . . . . ?
C38 C30 C31 C39 179.6(3) . . . . ?
B1 C30 C31 C39 2.5(4) . . . . ?
C30 C31 C32 C33 -0.9(5) . . . . ?
C39 C31 C32 C33 -179.9(3) . . . . ?
C31 C32 C33 C37 0.6(5) . . . . ?
O2 P2 C35 C36 61.5(4) . . . . ?
C47 P2 C35 C36 -60.6(4) . . . . ?
C101 P2 C35 C36 -178.5(3) . . . . ?
C32 C33 C37 C38 0.1(6) . . . . ?
C31 C30 C38 C37 0.2(5) . . . . ?
B1 C30 C38 C37 176.5(3) . . . . ?
C33 C37 C38 C30 -0.5(5) . . . . ?
C32 C31 C39 C40 -0.9(6) . . . . ?
C30 C31 C39 C40 -179.9(3) . . . . ?
C32 C31 C39 C44 179.2(3) . . . . ?
C30 C31 C39 C44 0.2(4) . . . . ?
C44 C39 C40 C41 0.1(5) . . . . ?
C31 C39 C40 C41 -179.8(3) . . . . ?
C39 C40 C41 C42 -0.2(6) . . . . ?
C40 C41 C42 C43 0.2(6) . . . . ?
C41 C42 C43 C44 -0.2(6) . . . . ?
C42 C43 C44 C39 0.1(5) . . . . ?
C42 C43 C44 B1 -176.4(4) . . . . ?
C40 C39 C44 C43 -0.1(5) . . . . ?
C31 C39 C44 C43 179.8(3) . . . . ?
C40 C39 C44 B1 177.2(3) . . . . ?
C31 C39 C44 B1 -2.9(4) . . . . ?
C27 C26 C45 C46 -1.7(6) . . . . ?
C26 C45 C46 C29 0.4(6) . . . . ?
C28 C29 C46 C45 1.1(5) . . . . ?
B1 C29 C46 C45 -175.1(3) . . . . ?
O2 P2 C47 C48 -172.7(3) . . . . ?
C35 P2 C47 C48 -54.5(4) . . . . ?
C101 P2 C47 C48 64.6(4) . . . . ?
P2 O2 B1 C44 -45.5(5) . . . . ?
P2 O2 B1 C29 -173.3(3) . . . . ?
P2 O2 B1 C30 65.5(4) . . . . ?
C43 C44 B1 O2 -60.7(5) . . . . ?
C39 C44 B1 O2 122.6(3) . . . . ?
C43 C44 B1 C29 60.2(5) . . . . ?
C39 C44 B1 C29 -116.5(3) . . . . ?
C43 C44 B1 C30 -179.3(4) . . . . ?
C39 C44 B1 C30 4.0(3) . . . . ?
C28 C29 B1 O2 144.3(3) . . . . ?
C46 C29 B1 O2 -39.8(4) . . . . ?
C28 C29 B1 C44 18.3(5) . . . . ?
C46 C29 B1 C44 -165.8(3) . . . . ?
C28 C29 B1 C30 -94.8(4) . . . . ?
C46 C29 B1 C30 81.0(4) . . . . ?
C38 C30 B1 O2 59.5(5) . . . . ?
C31 C30 B1 O2 -124.0(3) . . . . ?
C38 C30 B1 C44 179.6(3) . . . . ?
C31 C30 B1 C44 -3.8(3) . . . . ?
C38 C30 B1 C29 -56.8(5) . . . . ?
C31 C30 B1 C29 119.7(3) . . . . ?
O2 P2 C101 C34 43.7(4) . . . . ?
C47 P2 C101 C34 167.5(3) . . . . ?
C35 P2 C101 C34 -73.5(4) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive,Moisture-sensitive
