# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_cu_molan602_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2181177'
loop_
_audit_author_name
_audit_author_address
'Folkert de Vries'
;University of Groningen
Netherlands
;
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H26 B N3 O2'
_chemical_formula_weight         591.45

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.9788(3)
_cell_length_b                   15.3329(5)
_cell_length_c                   19.7187(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3017.04(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      4.48
_cell_measurement_theta_max      72.20

_exptl_crystal_description       block
_exptl_crystal_colour            'orange yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    0.634
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32344
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.484
_diffrn_reflns_theta_max         72.204
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5879
_reflns_number_gt                5729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.990

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+0.5725P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 2431 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5879
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
O1 O 0.30325(12) 0.57159(8) 0.30413(6) 0.0181(3) Uani 1 1 d . . . . .
C1 C 0.02401(17) 0.69800(12) 0.29759(9) 0.0187(4) Uani 1 1 d . . . . .
B1 B 0.3344(2) 0.66319(13) 0.29690(10) 0.0181(4) Uani 1 1 d . . . . .
N1 N 0.23732(14) 0.70182(9) 0.23764(7) 0.0167(3) Uani 1 1 d . . . . .
O2 O 0.33761(13) 0.71396(8) 0.35775(6) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.01895(18) 0.61318(12) 0.32341(9) 0.0209(4) Uani 1 1 d . . . . .
H2 H 0.074004 0.569332 0.303850 0.025 Uiso 1 1 calc R U . . .
N2 N 0.30867(15) 0.72024(10) 0.17852(7) 0.0196(3) Uani 1 1 d . . . . .
N3 N 0.46664(15) 0.67787(10) 0.25668(7) 0.0195(3) Uani 1 1 d . . . . .
C3 C -0.06475(19) 0.59171(13) 0.37697(10) 0.0248(4) Uani 1 1 d . . . . .
H3 H -0.068041 0.533494 0.393375 0.030 Uiso 1 1 calc R U . . .
C6 C -0.05952(19) 0.76260(12) 0.32566(9) 0.0222(4) Uani 1 1 d . . . . .
C5 C -0.13914(19) 0.73998(14) 0.38140(10) 0.0262(4) Uani 1 1 d . . . . .
H5 H -0.191703 0.783798 0.402681 0.031 Uiso 1 1 calc R U . . .
C4 C -0.14360(19) 0.65574(14) 0.40644(10) 0.0270(4) Uani 1 1 d . . . . .
H4 H -0.200340 0.641883 0.443595 0.032 Uiso 1 1 calc R U . . .
C7 C -0.0717(2) 0.85121(13) 0.29930(11) 0.0314(5) Uani 1 1 d . . . . .
H7 H -0.088863 0.895484 0.331867 0.038 Uiso 1 1 calc R U . . .
C16 C 0.43784(18) 0.70490(12) 0.19246(9) 0.0196(4) Uani 1 1 d . . . . .
C8 C -0.0616(2) 0.87771(13) 0.23468(11) 0.0337(5) Uani 1 1 d . . . . .
H8 H -0.073692 0.938398 0.227151 0.040 Uiso 1 1 calc R U . . .
C9 C -0.0345(2) 0.82521(12) 0.17433(10) 0.0260(4) Uani 1 1 d . . . . .
C15 C 0.10869(18) 0.71735(11) 0.23802(9) 0.0179(3) Uani 1 1 d . . . . .
C17 C 0.5433(2) 0.71421(13) 0.14491(9) 0.0245(4) Uani 1 1 d . . . . .
H17 H 0.525827 0.734837 0.100349 0.029 Uiso 1 1 calc R U . . .
C10 C -0.0880(2) 0.85291(14) 0.11191(11) 0.0315(5) Uani 1 1 d . . . . .
H10 H -0.133573 0.907210 0.109462 0.038 Uiso 1 1 calc R U . . .
C11 C -0.0754(2) 0.80261(15) 0.05410(11) 0.0332(5) Uani 1 1 d . . . . .
H11 H -0.112883 0.822245 0.012531 0.040 Uiso 1 1 calc R U . . .
C12 C -0.00802(19) 0.72329(15) 0.05668(10) 0.0285(4) Uani 1 1 d . . . . .
H12 H -0.002565 0.687517 0.017441 0.034 Uiso 1 1 calc R U . . .
C14 C 0.04052(18) 0.74772(12) 0.17536(9) 0.0205(4) Uani 1 1 d . . . . .
C13 C 0.05099(18) 0.69679(13) 0.11668(9) 0.0225(4) Uani 1 1 d . . . . .
H13 H 0.099215 0.643400 0.118097 0.027 Uiso 1 1 calc R U . . .
C19 C 0.69703(19) 0.66455(14) 0.23100(10) 0.0293(4) Uani 1 1 d . . . . .
H19 H 0.785651 0.649706 0.244291 0.035 Uiso 1 1 calc R U . . .
C20 C 0.59407(19) 0.65871(13) 0.27585(10) 0.0255(4) Uani 1 1 d . . . . .
H20 H 0.611387 0.641005 0.321184 0.031 Uiso 1 1 calc R U . . .
C21 C 0.39475(18) 0.52789(11) 0.34402(9) 0.0183(3) Uani 1 1 d . . . . .
C22 C 0.47823(19) 0.46598(12) 0.31230(9) 0.0226(4) Uani 1 1 d . . . . .
H22 H 0.462841 0.450314 0.266338 0.027 Uiso 1 1 calc R U . . .
C23 C 0.5810(2) 0.42851(12) 0.34731(10) 0.0241(4) Uani 1 1 d . . . . .
H23 H 0.636210 0.386221 0.325907 0.029 Uiso 1 1 calc R U . . .
C24 C 0.60551(19) 0.45258(12) 0.41572(10) 0.0220(4) Uani 1 1 d . . . . .
C25 C 0.71956(19) 0.41979(13) 0.45097(11) 0.0266(4) Uani 1 1 d . . . . .
H25 H 0.777112 0.379125 0.429227 0.032 Uiso 1 1 calc R U . . .
C26 C 0.7470(2) 0.44610(13) 0.51552(11) 0.0299(4) Uani 1 1 d . . . . .
H26 H 0.824724 0.425076 0.538047 0.036 Uiso 1 1 calc R U . . .
C27 C 0.6600(2) 0.50455(13) 0.54886(10) 0.0280(4) Uani 1 1 d . . . . .
H27 H 0.679256 0.522323 0.593972 0.034 Uiso 1 1 calc R U . . .
C28 C 0.54783(19) 0.53605(12) 0.51681(9) 0.0227(4) Uani 1 1 d . . . . .
H28 H 0.489962 0.574906 0.540273 0.027 Uiso 1 1 calc R U . . .
C29 C 0.51694(18) 0.51148(11) 0.44917(9) 0.0203(4) Uani 1 1 d . . . . .
C30 C 0.40487(18) 0.54696(11) 0.41248(9) 0.0180(3) Uani 1 1 d . . . . .
C31 C 0.30243(17) 0.60506(11) 0.44392(8) 0.0175(3) Uani 1 1 d . . . . .
C32 C 0.22293(17) 0.57724(12) 0.50077(9) 0.0183(4) Uani 1 1 d . . . . .
C33 C 0.23393(18) 0.49263(12) 0.52921(9) 0.0209(4) Uani 1 1 d . . . . .
H33 H 0.297634 0.452886 0.511138 0.025 Uiso 1 1 calc R U . . .
C34 C 0.1543(2) 0.46701(13) 0.58241(9) 0.0241(4) Uani 1 1 d . . . . .
H34 H 0.163525 0.409974 0.600636 0.029 Uiso 1 1 calc R U . . .
C35 C 0.0590(2) 0.52453(13) 0.61014(9) 0.0253(4) Uani 1 1 d . . . . .
H35 H 0.004698 0.506309 0.647078 0.030 Uiso 1 1 calc R U . . .
C36 C 0.0446(2) 0.60641(13) 0.58409(9) 0.0242(4) Uani 1 1 d . . . . .
H36 H -0.019942 0.644895 0.603055 0.029 Uiso 1 1 calc R U . . .
C37 C 0.12512(18) 0.63475(12) 0.52881(9) 0.0199(4) Uani 1 1 d . . . . .
C38 C 0.11020(18) 0.71947(12) 0.50086(9) 0.0213(4) Uani 1 1 d . . . . .
H38 H 0.049146 0.759462 0.520849 0.026 Uiso 1 1 calc R U . . .
C39 C 0.18284(18) 0.74379(11) 0.44556(9) 0.0203(4) Uani 1 1 d . . . . .
H39 H 0.171672 0.800533 0.427060 0.024 Uiso 1 1 calc R U . . .
C40 C 0.27451(18) 0.68545(11) 0.41553(9) 0.0182(4) Uani 1 1 d . . . . .
C18 C 0.6701(2) 0.69303(13) 0.16434(10) 0.0273(4) Uani 1 1 d . . . . .
H18 H 0.741390 0.697480 0.132596 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
O1 C21 1.379(2) . ?
O1 B1 1.445(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.408(3) . ?
C1 C15 1.477(2) . ?
B1 O2 1.431(2) . ?
B1 N3 1.556(2) . ?
B1 N1 1.629(2) . ?
N1 C15 1.305(2) . ?
N1 N2 1.395(2) . ?
O2 C40 1.373(2) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
N2 C16 1.339(2) . ?
N3 C20 1.359(2) . ?
N3 C16 1.363(2) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C6 C5 1.400(3) . ?
C6 C7 1.460(3) . ?
C5 C4 1.383(3) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C7 C8 1.341(3) . ?
C7 H7 0.9500 . ?
C16 C17 1.416(3) . ?
C8 C9 1.462(3) . ?
C8 H8 0.9500 . ?
C9 C14 1.404(3) . ?
C9 C10 1.407(3) . ?
C15 C14 1.485(2) . ?
C17 C18 1.362(3) . ?
C17 H17 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C14 C13 1.400(3) . ?
C13 H13 0.9500 . ?
C19 C20 1.359(3) . ?
C19 C18 1.411(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C30 1.385(2) . ?
C21 C22 1.409(3) . ?
C22 C23 1.363(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.420(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.425(3) . ?
C24 C29 1.426(3) . ?
C25 C26 1.363(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.410(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.373(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.420(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.439(2) . ?
C30 C31 1.491(2) . ?
C31 C40 1.382(2) . ?
C31 C32 1.438(2) . ?
C32 C33 1.418(3) . ?
C32 C37 1.427(3) . ?
C33 C34 1.374(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.407(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.364(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.422(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.419(3) . ?
C38 C39 1.361(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.410(3) . ?
C39 H39 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O1 B1 112.72(13) . . ?
C2 C1 C6 119.35(17) . . ?
C2 C1 C15 119.82(16) . . ?
C6 C1 C15 120.66(16) . . ?
O2 B1 O1 116.79(15) . . ?
O2 B1 N3 109.24(14) . . ?
O1 B1 N3 111.91(14) . . ?
O2 B1 N1 114.65(14) . . ?
O1 B1 N1 107.24(14) . . ?
N3 B1 N1 94.94(13) . . ?
C15 N1 N2 118.01(15) . . ?
C15 N1 B1 130.30(15) . . ?
N2 N1 B1 111.69(13) . . ?
C40 O2 B1 120.82(13) . . ?
C3 C2 C1 121.35(17) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C16 N2 N1 106.52(14) . . ?
C20 N3 C16 121.44(16) . . ?
C20 N3 B1 128.36(15) . . ?
C16 N3 B1 109.79(14) . . ?
C4 C3 C2 119.56(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C6 C1 118.06(17) . . ?
C5 C6 C7 117.57(18) . . ?
C1 C6 C7 124.35(17) . . ?
C4 C5 C6 121.99(18) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C4 C3 119.57(18) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C8 C7 C6 127.87(18) . . ?
C8 C7 H7 116.1 . . ?
C6 C7 H7 116.1 . . ?
N2 C16 N3 116.56(16) . . ?
N2 C16 C17 124.16(17) . . ?
N3 C16 C17 119.27(16) . . ?
C7 C8 C9 128.35(18) . . ?
C7 C8 H8 115.8 . . ?
C9 C8 H8 115.8 . . ?
C14 C9 C10 118.05(19) . . ?
C14 C9 C8 123.56(18) . . ?
C10 C9 C8 118.38(18) . . ?
N1 C15 C1 122.02(16) . . ?
N1 C15 C14 120.18(16) . . ?
C1 C15 C14 117.55(15) . . ?
C18 C17 C16 118.69(17) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C11 C10 C9 121.23(19) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.12(19) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.62(19) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C13 C14 C9 119.98(17) . . ?
C13 C14 C15 118.59(16) . . ?
C9 C14 C15 121.43(17) . . ?
C12 C13 C14 120.77(18) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C20 C19 C18 118.87(18) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 N3 120.82(18) . . ?
C19 C20 H20 119.6 . . ?
N3 C20 H20 119.6 . . ?
O1 C21 C30 120.11(16) . . ?
O1 C21 C22 117.75(15) . . ?
C30 C21 C22 122.12(17) . . ?
C23 C22 C21 120.24(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.10(17) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 120.63(18) . . ?
C23 C24 C29 119.83(17) . . ?
C25 C24 C29 119.53(17) . . ?
C26 C25 C24 120.77(19) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 119.97(18) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.72(19) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 121.06(18) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C28 C29 C24 117.92(17) . . ?
C28 C29 C30 122.75(17) . . ?
C24 C29 C30 119.25(16) . . ?
C21 C30 C29 117.85(16) . . ?
C21 C30 C31 118.78(16) . . ?
C29 C30 C31 123.34(16) . . ?
C40 C31 C32 117.97(16) . . ?
C40 C31 C30 120.18(15) . . ?
C32 C31 C30 121.68(15) . . ?
C33 C32 C37 117.72(16) . . ?
C33 C32 C31 122.49(16) . . ?
C37 C32 C31 119.75(16) . . ?
C34 C33 C32 121.27(17) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C35 120.56(18) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C36 C35 C34 120.13(17) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C37 120.66(18) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C38 C37 C36 121.20(17) . . ?
C38 C37 C32 119.15(16) . . ?
C36 C37 C32 119.66(17) . . ?
C39 C38 C37 120.39(17) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C38 C39 C40 120.54(17) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 H39 119.7 . . ?
O2 C40 C31 121.83(16) . . ?
O2 C40 C39 116.36(15) . . ?
C31 C40 C39 121.77(16) . . ?
C17 C18 C19 120.86(18) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_LP18028_xprep_a
_database_code_depnum_ccdc_archive 'CCDC 2181178'
loop_
_audit_author_name
_audit_author_address
'Lukas Pfeifer'
;Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2022-06-22 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H28 B Cl2 N3 O2'
_chemical_formula_weight         664.36

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   13.3750(4)
_cell_length_b                   6.5182(2)
_cell_length_c                   18.2995(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.2810(10)
_cell_angle_gamma                90
_cell_volume                     1578.73(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      74.37

_exptl_crystal_description       block
_exptl_crystal_colour            clear_dark_red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.187
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31206
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.440
_diffrn_reflns_theta_max         74.389
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             6297
_reflns_number_gt                5982
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.971

_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 APEX3 V2016.1-0'
_computing_cell_refinement       'Bruker SAINT 8.37A'
_computing_data_reduction        'Bruker SAINT 8.37A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0733P)²+1.0123P] 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 2513 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.081(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6297
_refine_ls_number_parameters     452
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.061
_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
O1 O 0.39831(17) 0.6803(4) 0.65367(12) 0.0179(5) Uani 1 1 d . . . . .
O2 O 0.38467(16) 0.3049(3) 0.65945(12) 0.0160(5) Uani 1 1 d . . . . .
N1 N 0.35602(18) 0.4687(4) 0.53567(13) 0.0141(5) Uani 1 1 d . . . . .
N2 N 0.42500(18) 0.4728(4) 0.48688(13) 0.0159(5) Uani 1 1 d . . . . .
N3 N 0.52120(18) 0.4798(4) 0.60113(13) 0.0149(5) Uani 1 1 d . . . . .
C1 C 0.2601(2) 0.4529(5) 0.50729(17) 0.0160(6) Uani 1 1 d . . . . .
C2 C 0.1720(2) 0.4237(5) 0.54724(18) 0.0173(6) Uani 1 1 d . . . . .
C3 C 0.1604(2) 0.4202(5) 0.62121(19) 0.0202(7) Uani 1 1 d . . . . .
H3 H 0.217784 0.433835 0.658041 0.024 Uiso 1 1 calc R U . . .
C4 C 0.0643(2) 0.3967(5) 0.64182(19) 0.0218(7) Uani 1 1 d . . . . .
C5 C 0.0478(3) 0.4012(6) 0.7204(2) 0.0262(7) Uani 1 1 d . . . . .
H5A H 0.012338 0.527771 0.730003 0.039 Uiso 1 1 calc R U . . .
H5B H 0.113161 0.396345 0.752394 0.039 Uiso 1 1 calc R U . . .
H5C H 0.007036 0.282512 0.730628 0.039 Uiso 1 1 calc R U . . .
C6 C -0.0194(2) 0.3712(5) 0.5858(2) 0.0236(7) Uani 1 1 d . . . . .
H6 H -0.084901 0.355100 0.599392 0.028 Uiso 1 1 calc R U . . .
C7 C -0.0085(3) 0.3691(6) 0.5125(2) 0.0245(7) Uani 1 1 d . . . . .
H7 H -0.065518 0.349385 0.475733 0.029 Uiso 1 1 calc R U . . .
C8 C 0.0867(2) 0.3962(5) 0.49273(19) 0.0204(7) Uani 1 1 d . . . . .
C9 C 0.1169(2) 0.4086(5) 0.41955(19) 0.0209(7) Uani 1 1 d . . . . .
C10 C 0.0602(3) 0.3888(6) 0.3500(2) 0.0275(8) Uani 1 1 d . . . . .
H10 H -0.009759 0.356554 0.344998 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1072(3) 0.4169(6) 0.2883(2) 0.0291(8) Uani 1 1 d . . . . .
H11 H 0.069158 0.402952 0.240489 0.035 Uiso 1 1 calc R U . . .
C12 C 0.2094(3) 0.4653(6) 0.29512(18) 0.0275(7) Uani 1 1 d . . . . .
H12 H 0.239869 0.489245 0.252081 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2680(3) 0.4790(6) 0.36491(17) 0.0231(7) Uani 1 1 d . . . . .
H13 H 0.338193 0.508257 0.369473 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2214(2) 0.4489(5) 0.42768(17) 0.0197(7) Uani 1 1 d . . . . .
C15 C 0.5174(2) 0.4760(5) 0.52664(16) 0.0146(5) Uani 1 1 d . . . . .
C16 C 0.6082(2) 0.4745(6) 0.49531(17) 0.0187(6) Uani 1 1 d . . . . .
H16 H 0.606721 0.470168 0.443282 0.022 Uiso 1 1 calc R U . . .
C17 C 0.6976(2) 0.4793(6) 0.54150(18) 0.0204(6) Uani 1 1 d . . . . .
H17 H 0.759289 0.478980 0.521404 0.024 Uiso 1 1 calc R U . . .
C18 C 0.6999(2) 0.4849(6) 0.61890(18) 0.0217(6) Uani 1 1 d . . . . .
H18 H 0.762389 0.486032 0.651003 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6106(2) 0.4887(5) 0.64660(17) 0.0185(6) Uani 1 1 d . . . . .
H19 H 0.611014 0.497759 0.698455 0.022 Uiso 1 1 calc R U . . .
C20 C 0.3406(2) 0.7109(5) 0.70836(17) 0.0175(6) Uani 1 1 d . . . . .
C21 C 0.2734(2) 0.8787(6) 0.69975(19) 0.0224(7) Uani 1 1 d . . . . .
H21 H 0.271072 0.965275 0.657766 0.027 Uiso 1 1 calc R U . . .
C22 C 0.2120(3) 0.9173(6) 0.7512(2) 0.0291(8) Uani 1 1 d . . . . .
H22 H 0.170278 1.035883 0.746657 0.035 Uiso 1 1 calc R U . . .
C23 C 0.2097(2) 0.7828(7) 0.8115(2) 0.0296(9) Uani 1 1 d . . . . .
C24 C 0.1379(3) 0.8060(9) 0.8617(2) 0.0425(12) Uani 1 1 d . . . . .
H24 H 0.094476 0.922050 0.857497 0.051 Uiso 1 1 calc R U . . .
C25 C 0.1308(3) 0.6660(11) 0.9149(2) 0.0527(16) Uani 1 1 d . . . . .
H25 H 0.082472 0.684102 0.947595 0.063 Uiso 1 1 calc R U . . .
C26 C 0.1942(3) 0.4938(10) 0.9222(2) 0.0477(13) Uani 1 1 d . . . . .
H26 H 0.186701 0.393511 0.958736 0.057 Uiso 1 1 calc R U . . .
C27 C 0.2673(3) 0.4684(8) 0.87718(18) 0.0334(9) Uani 1 1 d . . . . .
H27 H 0.310867 0.352724 0.883653 0.040 Uiso 1 1 calc R U . . .
C28 C 0.2779(2) 0.6140(7) 0.82102(17) 0.0249(8) Uani 1 1 d . . . . .
C29 C 0.3502(2) 0.5876(6) 0.77067(17) 0.0192(7) Uani 1 1 d . . . . .
C30 C 0.4388(2) 0.2841(5) 0.72915(17) 0.0182(6) Uani 1 1 d . . . . .
C31 C 0.5030(2) 0.1116(5) 0.7422(2) 0.0226(7) Uani 1 1 d . . . . .
H31 H 0.505185 0.012087 0.704492 0.027 Uiso 1 1 calc R U . . .
C32 C 0.5620(3) 0.0885(6) 0.8093(2) 0.0294(8) Uani 1 1 d . . . . .
H32 H 0.602447 -0.030871 0.819128 0.035 Uiso 1 1 calc R U . . .
C33 C 0.5628(3) 0.2421(7) 0.8643(2) 0.0285(8) Uani 1 1 d . . . . .
C34 C 0.6300(3) 0.2311(8) 0.9321(2) 0.0383(10) Uani 1 1 d . . . . .
H34 H 0.672196 0.114159 0.942120 0.046 Uiso 1 1 calc R U . . .
C35 C 0.6348(3) 0.3851(9) 0.9826(2) 0.0426(11) Uani 1 1 d . . . . .
H35 H 0.680637 0.375520 1.027293 0.051 Uiso 1 1 calc R U . . .
C36 C 0.5721(3) 0.5589(8) 0.9690(2) 0.0400(11) Uani 1 1 d . . . . .
H36 H 0.576807 0.667131 1.004130 0.048 Uiso 1 1 calc R U . . .
C37 C 0.5042(3) 0.5725(7) 0.90524(19) 0.0309(9) Uani 1 1 d . . . . .
H37 H 0.461404 0.689031 0.897089 0.037 Uiso 1 1 calc R U . . .
C38 C 0.4974(2) 0.4149(6) 0.85160(18) 0.0245(8) Uani 1 1 d . . . . .
C39 C 0.4285(2) 0.4262(5) 0.78320(17) 0.0190(7) Uani 1 1 d . . . . .
B1 B 0.4113(2) 0.4839(6) 0.62117(17) 0.0143(6) Uani 1 1 d . . . . .
Cl1 Cl 0.90179(18) 0.2958(3) 0.88276(11) 0.0838(6) Uani 0.9 1 d D . P A 1
Cl2 Cl 0.83445(13) 0.7274(3) 0.89509(9) 0.0657(5) Uani 0.9 1 d D . P A 1
C40 C 0.8179(6) 0.4870(16) 0.8434(3) 0.100(3) Uani 0.9 1 d D . P A 1
H40A H 0.747594 0.438341 0.842301 0.120 Uiso 0.9 1 calc R U P A 1
H40B H 0.829237 0.511793 0.791880 0.120 Uiso 0.9 1 calc R U P A 1
Cl1' Cl 0.919(4) 0.328(8) 0.8326(19) 0.34(3) Uani 0.1 1 d D U P B 2
Cl2' Cl 0.8653(17) 0.615(4) 0.9394(9) 0.099(6) Uani 0.1 1 d D U P B 2
C40' C 0.8179(6) 0.4870(16) 0.8434(3) 0.100(3) Uani 0.1 1 d D U P B 2
H40C H 0.755163 0.407359 0.844699 0.120 Uiso 0.1 1 calc R U P B 2
H40D H 0.806225 0.590695 0.803588 0.120 Uiso 0.1 1 calc R U P B 2


_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
O1 C20 1.364(4) . ?
O1 B1 1.433(4) . ?
O2 C30 1.379(4) . ?
O2 B1 1.432(4) . ?
N1 C1 1.317(4) . ?
N1 N2 1.373(3) . ?
N1 B1 1.634(4) . ?
N2 C15 1.341(4) . ?
N3 C19 1.356(4) . ?
N3 C15 1.357(4) . ?
N3 B1 1.566(4) . ?
C1 C14 1.475(4) . ?
C1 C2 1.486(4) . ?
C2 C3 1.385(5) . ?
C2 C8 1.415(4) . ?
C3 C4 1.399(4) . ?
C3 H3 0.9500 . ?
C4 C6 1.415(5) . ?
C4 C5 1.486(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.371(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.456(5) . ?
C9 C10 1.391(5) . ?
C9 C14 1.408(4) . ?
C10 C11 1.382(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.398(5) . ?
C13 H13 0.9500 . ?
C15 C16 1.415(4) . ?
C16 C17 1.362(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.413(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.363(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C29 1.386(5) . ?
C20 C21 1.410(5) . ?
C21 C22 1.360(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.412(6) . ?
C22 H22 0.9500 . ?
C23 C28 1.423(6) . ?
C23 C24 1.430(5) . ?
C24 C25 1.347(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.402(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.421(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.439(4) . ?
C29 C39 1.479(5) . ?
C30 C39 1.377(5) . ?
C30 C31 1.414(5) . ?
C31 C32 1.370(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.418(6) . ?
C32 H32 0.9500 . ?
C33 C38 1.425(6) . ?
C33 C34 1.425(5) . ?
C34 C35 1.361(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.410(7) . ?
C35 H35 0.9500 . ?
C36 C37 1.375(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.415(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.445(4) . ?
Cl1 C40 1.760(11) . ?
Cl2 C40 1.827(10) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
Cl1' C40' 1.74(3) . ?
Cl2' C40' 1.964(19) . ?
C40' H40C 0.9900 . ?
C40' H40D 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
C20 O1 B1 123.4(3) . . ?
C30 O2 B1 113.5(2) . . ?
C1 N1 N2 116.9(2) . . ?
C1 N1 B1 131.5(2) . . ?
N2 N1 B1 111.6(2) . . ?
C15 N2 N1 107.5(2) . . ?
C19 N3 C15 121.3(2) . . ?
C19 N3 B1 129.1(2) . . ?
C15 N3 B1 109.6(2) . . ?
N1 C1 C14 125.1(3) . . ?
N1 C1 C2 127.8(3) . . ?
C14 C1 C2 107.0(3) . . ?
C3 C2 C8 119.6(3) . . ?
C3 C2 C1 133.8(3) . . ?
C8 C2 C1 106.6(3) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C6 118.7(3) . . ?
C3 C4 C5 121.9(3) . . ?
C6 C4 C5 119.4(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.7(3) . . ?
C7 C6 H6 119.1 . . ?
C4 C6 H6 119.1 . . ?
C6 C7 C8 119.1(3) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C8 C2 120.7(3) . . ?
C7 C8 C9 129.5(3) . . ?
C2 C8 C9 109.8(3) . . ?
C10 C9 C14 121.1(3) . . ?
C10 C9 C8 130.5(3) . . ?
C14 C9 C8 108.4(3) . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C9 119.5(3) . . ?
C13 C14 C1 132.4(3) . . ?
C9 C14 C1 108.1(3) . . ?
N2 C15 N3 116.3(3) . . ?
N2 C15 C16 123.9(3) . . ?
N3 C15 C16 119.8(3) . . ?
C17 C16 C15 118.5(3) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
N3 C19 C18 120.9(3) . . ?
N3 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
O1 C20 C29 121.6(3) . . ?
O1 C20 C21 116.8(3) . . ?
C29 C20 C21 121.6(3) . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C28 119.4(3) . . ?
C22 C23 C24 121.9(4) . . ?
C28 C23 C24 118.7(4) . . ?
C25 C24 C23 121.1(5) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 120.5(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 120.7(5) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 120.4(4) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 118.5(3) . . ?
C27 C28 C29 122.0(4) . . ?
C23 C28 C29 119.4(3) . . ?
C20 C29 C28 117.8(3) . . ?
C20 C29 C39 121.3(3) . . ?
C28 C29 C39 120.8(3) . . ?
C39 C30 O2 120.3(3) . . ?
C39 C30 C31 122.4(3) . . ?
O2 C30 C31 117.3(3) . . ?
C32 C31 C30 119.7(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 120.2(4) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C38 120.1(3) . . ?
C32 C33 C34 121.4(4) . . ?
C38 C33 C34 118.5(4) . . ?
C35 C34 C33 121.1(4) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C34 C35 C36 120.3(3) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C37 C36 C35 120.3(4) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 120.7(4) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C37 C38 C33 119.0(3) . . ?
C37 C38 C39 122.2(3) . . ?
C33 C38 C39 118.8(3) . . ?
C30 C39 C38 118.1(3) . . ?
C30 C39 C29 120.6(3) . . ?
C38 C39 C29 121.3(3) . . ?
O2 B1 O1 118.1(3) . . ?
O2 B1 N3 114.1(3) . . ?
O1 B1 N3 106.7(3) . . ?
O2 B1 N1 108.0(2) . . ?
O1 B1 N1 112.7(3) . . ?
N3 B1 N1 94.9(2) . . ?
Cl1 C40 Cl2 111.9(3) . . ?
Cl1 C40 H40A 109.2 . . ?
Cl2 C40 H40A 109.2 . . ?
Cl1 C40 H40B 109.2 . . ?
Cl2 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
Cl1' C40' Cl2' 101.5(17) . . ?
Cl1' C40' H40C 111.5 . . ?
Cl2' C40' H40C 111.5 . . ?
Cl1' C40' H40D 111.5 . . ?
Cl2' C40' H40D 111.5 . . ?
H40C C40' H40D 109.3 . . ?

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.060

