# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_170206c1
_database_code_depnum_ccdc_archive 'CCDC 1885421'
loop_
_audit_author_name
_audit_author_address
'Chihiro MAEDA'
;Okayama University
Japan
;
_audit_update_record             
;
2018-12-17 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H22 B N2 O2 S'
_chemical_formula_sum            'C39 H22 B N2 O2 S'
_chemical_formula_weight         593.45

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'
S S 0.3331 0.5567 '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                   12.978(2)
_cell_length_b                   6.7317(11)
_cell_length_c                   16.309(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.116(5)
_cell_angle_gamma                90
_cell_volume                     1419.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1541
_cell_measurement_theta_min      25.2
_cell_measurement_theta_max      68.2

_exptl_crystal_description       prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             614
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.337
_shelx_estimated_absorpt_T_min   0.825
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            18311
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.691
_diffrn_reflns_theta_max         66.971
_diffrn_reflns_theta_full        66.971
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4918
_reflns_number_gt                4447
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_max     0.971
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4918
_refine_ls_number_parameters     406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.010
_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
C1 C 0.9029(2) 0.4465(4) 0.62362(18) 0.0268(7) Uani 1 1 d . . . . .
H1 H 0.8891 0.4446 0.6799 0.032 Uiso 1 1 calc R U . . .
C2 C 1.0010(3) 0.4853(4) 0.6005(2) 0.0316(7) Uani 1 1 d . . . . .
H2 H 1.0556 0.5089 0.6422 0.038 Uiso 1 1 calc R U . . .
C3 C 1.0223(3) 0.4909(5) 0.5184(2) 0.0341(8) Uani 1 1 d . . . . .
H3 H 1.0907 0.5182 0.5053 0.041 Uiso 1 1 calc R U . . .
C4 C 0.9457(3) 0.4575(4) 0.45584(19) 0.0301(7) Uani 1 1 d . . . . .
H4 H 0.9604 0.4621 0.3998 0.036 Uiso 1 1 calc R U . . .
C5 C 0.8460(3) 0.4168(4) 0.47679(18) 0.0276(7) Uani 1 1 d . . . . .
C6 C 0.8245(2) 0.4100(4) 0.56034(17) 0.0235(6) Uani 1 1 d . . . . .
C7 C 0.6751(2) 0.3511(4) 0.48650(15) 0.0221(6) Uani 1 1 d . . . . .
C8 C 0.7499(2) 0.3733(3) 0.42631(16) 0.0199(6) Uani 1 1 d . . . . .
C9 C 0.7144(3) 0.3591(5) 0.34420(17) 0.0313(7) Uani 1 1 d . . . . .
H5 H 0.7619 0.3679 0.3033 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6099(3) 0.3323(5) 0.32096(17) 0.0333(7) Uani 1 1 d . . . . .
H6 H 0.5876 0.3200 0.2641 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5365(3) 0.3225(5) 0.37848(17) 0.0303(6) Uani 1 1 d . . . . .
C12 C 0.5694(2) 0.3334(5) 0.46339(15) 0.0244(6) Uani 1 1 d . . . . .
C13 C 0.5016(2) 0.3352(5) 0.52814(15) 0.0233(6) Uani 1 1 d . . . . .
C14 C 0.3570(2) 0.3383(5) 0.61359(16) 0.0259(6) Uani 1 1 d . . . . .
C15 C 0.2651(2) 0.3378(5) 0.65120(17) 0.0284(6) Uani 1 1 d . . . . .
H7 H 0.1999 0.3368 0.6196 0.034 Uiso 1 1 calc R U . . .
C16 C 0.2719(2) 0.3386(5) 0.73618(18) 0.0324(6) Uani 1 1 d . . . . .
H8 H 0.2105 0.3427 0.7638 0.039 Uiso 1 1 calc R U . . .
C17 C 0.3678(2) 0.3335(6) 0.78170(17) 0.0310(6) Uani 1 1 d . . . . .
H9 H 0.3704 0.3313 0.8401 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4600(2) 0.3315(5) 0.74436(16) 0.0278(6) Uani 1 1 d . . . . .
H10 H 0.5249 0.3262 0.7762 0.033 Uiso 1 1 calc R U . . .
C19 C 0.7645(2) 0.1230(4) 0.72973(17) 0.0249(6) Uani 1 1 d . . . . .
C20 C 0.8253(3) -0.0372(5) 0.70446(19) 0.0305(7) Uani 1 1 d . . . . .
H11 H 0.8007 -0.1174 0.6589 0.037 Uiso 1 1 calc R U . . .
C21 C 0.9194(3) -0.0755(5) 0.74593(19) 0.0334(8) Uani 1 1 d . . . . .
H12 H 0.9581 -0.1868 0.7304 0.040 Uiso 1 1 calc R U . . .
C22 C 0.9606(3) 0.0471(5) 0.8117(2) 0.0341(8) Uani 1 1 d . . . . .
C23 C 1.0608(3) 0.0174(6) 0.8516(2) 0.0416(8) Uani 1 1 d . . . . .
H13 H 1.1012 -0.0916 0.8359 0.050 Uiso 1 1 calc R U . . .
C24 C 1.1004(3) 0.1426(7) 0.9122(2) 0.0473(10) Uani 1 1 d . . . . .
H14 H 1.1678 0.1199 0.9383 0.057 Uiso 1 1 calc R U . . .
C25 C 1.0417(3) 0.3058(7) 0.9364(2) 0.0450(10) Uani 1 1 d . . . . .
H15 H 1.0702 0.3945 0.9777 0.054 Uiso 1 1 calc R U . . .
C26 C 0.9433(2) 0.3356(7) 0.90008(18) 0.0373(7) Uani 1 1 d . . . . .
H16 H 0.9041 0.4446 0.9174 0.045 Uiso 1 1 calc R U . . .
C27 C 0.8987(3) 0.2086(5) 0.83759(18) 0.0304(7) Uani 1 1 d . . . . .
C28 C 0.7964(2) 0.2373(5) 0.79817(18) 0.0284(7) Uani 1 1 d . . . . .
C29 C 0.7259(2) 0.3912(4) 0.82758(18) 0.0283(7) Uani 1 1 d . . . . .
C30 C 0.7000(2) 0.3927(5) 0.91173(18) 0.0327(8) Uani 1 1 d . . . . .
C31 C 0.7267(3) 0.2330(6) 0.9662(2) 0.0403(9) Uani 1 1 d . . . . .
H17 H 0.7645 0.1229 0.9481 0.048 Uiso 1 1 calc R U . . .
C32 C 0.6973(3) 0.2381(7) 1.0460(2) 0.0517(11) Uani 1 1 d . . . . .
H18 H 0.7159 0.1316 1.0825 0.062 Uiso 1 1 calc R U . . .
C33 C 0.6405(3) 0.3988(7) 1.0733(2) 0.0505(12) Uani 1 1 d . . . . .
H19 H 0.6220 0.4008 1.1284 0.061 Uiso 1 1 calc R U . . .
C34 C 0.6118(3) 0.5510(7) 1.0219(2) 0.0488(11) Uani 1 1 d . . . . .
H20 H 0.5716 0.6564 1.0411 0.059 Uiso 1 1 calc R U . . .
C35 C 0.6407(3) 0.5560(6) 0.93976(19) 0.0375(8) Uani 1 1 d . . . . .
C36 C 0.6130(3) 0.7141(5) 0.8856(2) 0.0362(8) Uani 1 1 d . . . . .
H21 H 0.5812 0.8292 0.9056 0.043 Uiso 1 1 calc R U . . .
C37 C 0.6314(2) 0.7034(5) 0.80464(19) 0.0304(7) Uani 1 1 d . . . . .
H22 H 0.6107 0.8095 0.7684 0.037 Uiso 1 1 calc R U . . .
S1 S 0.36871(5) 0.33606(11) 0.50779(4) 0.02691(19) Uani 1 1 d . . . . .
O1 O 0.67096(17) 0.1591(3) 0.68633(12) 0.0247(5) Uani 1 1 d . . . . .
N1 N 0.71938(18) 0.3672(3) 0.56571(13) 0.0222(5) Uani 1 1 d . . . . .
O2 O 0.68504(17) 0.5251(3) 0.69130(12) 0.0262(5) Uani 1 1 d . . . . .
N2 N 0.53666(17) 0.3401(4) 0.60768(13) 0.0235(5) Uani 1 1 d . . . . .
C38 C 0.4539(2) 0.3376(5) 0.65859(16) 0.0250(6) Uani 1 1 d . . . . .
C39 C 0.6815(2) 0.5336(5) 0.77420(17) 0.0266(6) Uani 1 1 d . . . . .
B1 B 0.6589(2) 0.3459(6) 0.64282(17) 0.0234(6) 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
C1 C2 1.384(4) . ?
C1 C6 1.405(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.416(4) . ?
C5 C8 1.462(5) . ?
C6 N1 1.404(4) . ?
C7 N1 1.371(4) . ?
C7 C12 1.395(4) . ?
C7 C8 1.449(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.386(5) . ?
C9 H5 0.9500 . ?
C10 C11 1.397(4) . ?
C10 H6 0.9500 . ?
C11 C12 1.414(4) . ?
C12 C13 1.433(4) . ?
C13 N2 1.336(3) . ?
C13 S1 1.727(3) . ?
C14 C15 1.389(4) . ?
C14 C38 1.398(4) . ?
C14 S1 1.746(3) . ?
C15 C16 1.381(4) . ?
C15 H7 0.9500 . ?
C16 C17 1.392(5) . ?
C16 H8 0.9500 . ?
C17 C18 1.390(4) . ?
C17 H9 0.9500 . ?
C18 C38 1.395(4) . ?
C18 H10 0.9500 . ?
C19 O1 1.372(4) . ?
C19 C28 1.388(4) . ?
C19 C20 1.418(4) . ?
C20 C21 1.367(5) . ?
C20 H11 0.9500 . ?
C21 C22 1.420(5) . ?
C21 H12 0.9500 . ?
C22 C23 1.416(5) . ?
C22 C27 1.437(5) . ?
C23 C24 1.364(6) . ?
C23 H13 0.9500 . ?
C24 C25 1.413(6) . ?
C24 H14 0.9500 . ?
C25 C26 1.375(5) . ?
C25 H15 0.9500 . ?
C26 C27 1.414(5) . ?
C26 H16 0.9500 . ?
C27 C28 1.436(5) . ?
C28 C29 1.489(4) . ?
C29 C39 1.385(4) . ?
C29 C30 1.442(4) . ?
C30 C31 1.417(5) . ?
C30 C35 1.440(5) . ?
C31 C32 1.389(5) . ?
C31 H17 0.9500 . ?
C32 C33 1.403(6) . ?
C32 H18 0.9500 . ?
C33 C34 1.355(6) . ?
C33 H19 0.9500 . ?
C34 C35 1.423(4) . ?
C34 H20 0.9500 . ?
C35 C36 1.409(5) . ?
C36 C37 1.364(4) . ?
C36 H21 0.9500 . ?
C37 C39 1.426(4) . ?
C37 H22 0.9500 . ?
O1 B1 1.446(4) . ?
N1 B1 1.547(3) . ?
O2 C39 1.358(3) . ?
O2 B1 1.465(4) . ?
N2 C38 1.415(3) . ?
N2 B1 1.638(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.2(3) . . ?
C2 C1 H1 121.4 . . ?
C6 C1 H1 121.4 . . ?
C1 C2 C3 122.2(3) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 C8 131.7(3) . . ?
C6 C5 C8 107.7(2) . . ?
N1 C6 C1 129.3(2) . . ?
N1 C6 C5 110.0(3) . . ?
C1 C6 C5 120.6(3) . . ?
N1 C7 C12 125.5(2) . . ?
N1 C7 C8 112.3(2) . . ?
C12 C7 C8 121.9(2) . . ?
C9 C8 C7 117.7(3) . . ?
C9 C8 C5 139.0(3) . . ?
C7 C8 C5 103.2(2) . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 H5 119.7 . . ?
C10 C9 H5 119.7 . . ?
C9 C10 C11 122.1(3) . . ?
C9 C10 H6 119.0 . . ?
C11 C10 H6 119.0 . . ?
C10 C11 C12 119.4(3) . . ?
C7 C12 C11 118.2(2) . . ?
C7 C12 C13 117.0(2) . . ?
C11 C12 C13 124.8(3) . . ?
N2 C13 C12 122.5(3) . . ?
N2 C13 S1 115.73(19) . . ?
C12 C13 S1 121.8(2) . . ?
C15 C14 C38 122.4(2) . . ?
C15 C14 S1 126.2(2) . . ?
C38 C14 S1 111.41(19) . . ?
C16 C15 C14 117.5(3) . . ?
C16 C15 H7 121.2 . . ?
C14 C15 H7 121.2 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H8 119.7 . . ?
C17 C16 H8 119.7 . . ?
C18 C17 C16 122.0(3) . . ?
C18 C17 H9 119.0 . . ?
C16 C17 H9 119.0 . . ?
C17 C18 C38 117.7(3) . . ?
C17 C18 H10 121.1 . . ?
C38 C18 H10 121.1 . . ?
O1 C19 C28 120.2(3) . . ?
O1 C19 C20 118.3(3) . . ?
C28 C19 C20 121.4(3) . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H11 120.2 . . ?
C19 C20 H11 120.2 . . ?
C20 C21 C22 121.6(3) . . ?
C20 C21 H12 119.2 . . ?
C22 C21 H12 119.2 . . ?
C23 C22 C21 122.3(3) . . ?
C23 C22 C27 119.1(3) . . ?
C21 C22 C27 118.6(3) . . ?
C24 C23 C22 121.1(4) . . ?
C24 C23 H13 119.4 . . ?
C22 C23 H13 119.4 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H14 119.8 . . ?
C25 C24 H14 119.8 . . ?
C26 C25 C24 119.8(4) . . ?
C26 C25 H15 120.1 . . ?
C24 C25 H15 120.1 . . ?
C25 C26 C27 121.8(4) . . ?
C25 C26 H16 119.1 . . ?
C27 C26 H16 119.1 . . ?
C26 C27 C28 122.9(3) . . ?
C26 C27 C22 117.8(3) . . ?
C28 C27 C22 119.3(3) . . ?
C19 C28 C27 118.8(3) . . ?
C19 C28 C29 119.8(3) . . ?
C27 C28 C29 121.3(3) . . ?
C39 C29 C30 118.3(3) . . ?
C39 C29 C28 120.8(3) . . ?
C30 C29 C28 120.9(3) . . ?
C31 C30 C35 119.2(3) . . ?
C31 C30 C29 121.7(3) . . ?
C35 C30 C29 119.0(3) . . ?
C32 C31 C30 119.7(4) . . ?
C32 C31 H17 120.1 . . ?
C30 C31 H17 120.1 . . ?
C31 C32 C33 120.8(4) . . ?
C31 C32 H18 119.6 . . ?
C33 C32 H18 119.6 . . ?
C34 C33 C32 120.6(3) . . ?
C34 C33 H19 119.7 . . ?
C32 C33 H19 119.7 . . ?
C33 C34 C35 121.3(4) . . ?
C33 C34 H20 119.4 . . ?
C35 C34 H20 119.4 . . ?
C36 C35 C34 122.3(3) . . ?
C36 C35 C30 119.4(3) . . ?
C34 C35 C30 118.3(3) . . ?
C37 C36 C35 120.7(3) . . ?
C37 C36 H21 119.6 . . ?
C35 C36 H21 119.6 . . ?
C36 C37 C39 120.2(3) . . ?
C36 C37 H22 119.9 . . ?
C39 C37 H22 119.9 . . ?
C13 S1 C14 89.07(12) . . ?
C19 O1 B1 117.4(2) . . ?
C7 N1 C6 106.6(2) . . ?
C7 N1 B1 123.9(2) . . ?
C6 N1 B1 129.5(2) . . ?
C39 O2 B1 123.0(2) . . ?
C13 N2 C38 111.0(2) . . ?
C13 N2 B1 125.1(2) . . ?
C38 N2 B1 123.8(2) . . ?
C18 C38 C14 119.6(2) . . ?
C18 C38 N2 127.6(3) . . ?
C14 C38 N2 112.7(2) . . ?
O2 C39 C29 123.2(3) . . ?
O2 C39 C37 115.9(3) . . ?
C29 C39 C37 120.9(3) . . ?
O1 B1 O2 116.2(2) . . ?
O1 B1 N1 116.1(3) . . ?
O2 B1 N1 104.6(2) . . ?
O1 B1 N2 102.1(2) . . ?
O2 B1 N2 112.3(2) . . ?
N1 B1 N2 105.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 C8 -179.2(3) . . . . ?
C2 C1 C6 N1 -180.0(3) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C4 C5 C6 N1 179.8(3) . . . . ?
C8 C5 C6 N1 -0.8(3) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C8 C5 C6 C1 -179.9(2) . . . . ?
N1 C7 C8 C9 179.8(2) . . . . ?
C12 C7 C8 C9 -5.5(4) . . . . ?
N1 C7 C8 C5 -3.1(3) . . . . ?
C12 C7 C8 C5 171.6(3) . . . . ?
C4 C5 C8 C9 -2.4(6) . . . . ?
C6 C5 C8 C9 178.4(3) . . . . ?
C4 C5 C8 C7 -178.5(3) . . . . ?
C6 C5 C8 C7 2.3(3) . . . . ?
C7 C8 C9 C10 2.4(4) . . . . ?
C5 C8 C9 C10 -173.3(3) . . . . ?
C8 C9 C10 C11 1.4(5) . . . . ?
C9 C10 C11 C12 -2.2(5) . . . . ?
N1 C7 C12 C11 178.6(3) . . . . ?
C8 C7 C12 C11 4.7(4) . . . . ?
N1 C7 C12 C13 0.9(5) . . . . ?
C8 C7 C12 C13 -173.0(3) . . . . ?
C10 C11 C12 C7 -0.8(5) . . . . ?
C10 C11 C12 C13 176.7(3) . . . . ?
C7 C12 C13 N2 -4.4(5) . . . . ?
C11 C12 C13 N2 178.1(3) . . . . ?
C7 C12 C13 S1 174.3(2) . . . . ?
C11 C12 C13 S1 -3.2(5) . . . . ?
C38 C14 C15 C16 0.7(5) . . . . ?
S1 C14 C15 C16 179.6(3) . . . . ?
C14 C15 C16 C17 -2.1(5) . . . . ?
C15 C16 C17 C18 1.3(5) . . . . ?
C16 C17 C18 C38 0.9(5) . . . . ?
O1 C19 C20 C21 179.3(3) . . . . ?
C28 C19 C20 C21 -2.9(4) . . . . ?
C19 C20 C21 C22 -3.0(4) . . . . ?
C20 C21 C22 C23 -175.7(3) . . . . ?
C20 C21 C22 C27 3.4(4) . . . . ?
C21 C22 C23 C24 177.1(3) . . . . ?
C27 C22 C23 C24 -2.0(5) . . . . ?
C22 C23 C24 C25 -0.1(5) . . . . ?
C23 C24 C25 C26 1.6(5) . . . . ?
C24 C25 C26 C27 -1.0(5) . . . . ?
C25 C26 C27 C28 -179.5(3) . . . . ?
C25 C26 C27 C22 -1.1(5) . . . . ?
C23 C22 C27 C26 2.5(4) . . . . ?
C21 C22 C27 C26 -176.6(3) . . . . ?
C23 C22 C27 C28 -179.0(3) . . . . ?
C21 C22 C27 C28 1.9(4) . . . . ?
O1 C19 C28 C27 -174.1(2) . . . . ?
C20 C19 C28 C27 8.0(4) . . . . ?
O1 C19 C28 C29 3.8(4) . . . . ?
C20 C19 C28 C29 -174.0(3) . . . . ?
C26 C27 C28 C19 170.9(3) . . . . ?
C22 C27 C28 C19 -7.5(4) . . . . ?
C26 C27 C28 C29 -7.0(4) . . . . ?
C22 C27 C28 C29 174.6(3) . . . . ?
C19 C28 C29 C39 -52.5(4) . . . . ?
C27 C28 C29 C39 125.4(3) . . . . ?
C19 C28 C29 C30 125.8(3) . . . . ?
C27 C28 C29 C30 -56.3(4) . . . . ?
C39 C29 C30 C31 168.5(3) . . . . ?
C28 C29 C30 C31 -9.8(5) . . . . ?
C39 C29 C30 C35 -8.2(4) . . . . ?
C28 C29 C30 C35 173.4(3) . . . . ?
C35 C30 C31 C32 -1.3(5) . . . . ?
C29 C30 C31 C32 -178.0(3) . . . . ?
C30 C31 C32 C33 0.6(5) . . . . ?
C31 C32 C33 C34 1.0(6) . . . . ?
C32 C33 C34 C35 -1.9(6) . . . . ?
C33 C34 C35 C36 -179.1(4) . . . . ?
C33 C34 C35 C30 1.1(5) . . . . ?
C31 C30 C35 C36 -179.3(3) . . . . ?
C29 C30 C35 C36 -2.5(5) . . . . ?
C31 C30 C35 C34 0.5(5) . . . . ?
C29 C30 C35 C34 177.3(3) . . . . ?
C34 C35 C36 C37 -172.3(3) . . . . ?
C30 C35 C36 C37 7.5(5) . . . . ?
C35 C36 C37 C39 -1.6(5) . . . . ?
N2 C13 S1 C14 -1.1(3) . . . . ?
C12 C13 S1 C14 -180.0(3) . . . . ?
C15 C14 S1 C13 -179.3(3) . . . . ?
C38 C14 S1 C13 -0.2(3) . . . . ?
C28 C19 O1 B1 66.4(3) . . . . ?
C20 C19 O1 B1 -115.7(3) . . . . ?
C12 C7 N1 C6 -171.8(3) . . . . ?
C8 C7 N1 C6 2.7(3) . . . . ?
C12 C7 N1 B1 6.8(5) . . . . ?
C8 C7 N1 B1 -178.8(3) . . . . ?
C1 C6 N1 C7 177.9(3) . . . . ?
C5 C6 N1 C7 -1.1(3) . . . . ?
C1 C6 N1 B1 -0.6(5) . . . . ?
C5 C6 N1 B1 -179.5(3) . . . . ?
C12 C13 N2 C38 -179.1(3) . . . . ?
S1 C13 N2 C38 2.1(3) . . . . ?
C12 C13 N2 B1 0.4(5) . . . . ?
S1 C13 N2 B1 -178.4(2) . . . . ?
C17 C18 C38 C14 -2.3(5) . . . . ?
C17 C18 C38 N2 178.9(3) . . . . ?
C15 C14 C38 C18 1.5(5) . . . . ?
S1 C14 C38 C18 -177.6(3) . . . . ?
C15 C14 C38 N2 -179.5(3) . . . . ?
S1 C14 C38 N2 1.4(4) . . . . ?
C13 N2 C38 C18 176.6(3) . . . . ?
B1 N2 C38 C18 -2.8(5) . . . . ?
C13 N2 C38 C14 -2.2(4) . . . . ?
B1 N2 C38 C14 178.3(3) . . . . ?
B1 O2 C39 C29 48.4(4) . . . . ?
B1 O2 C39 C37 -133.4(3) . . . . ?
C30 C29 C39 O2 -167.6(3) . . . . ?
C28 C29 C39 O2 10.7(5) . . . . ?
C30 C29 C39 C37 14.4(4) . . . . ?
C28 C29 C39 C37 -167.3(3) . . . . ?
C36 C37 C39 O2 172.2(3) . . . . ?
C36 C37 C39 C29 -9.7(5) . . . . ?
C19 O1 B1 O2 -52.3(3) . . . . ?
C19 O1 B1 N1 71.3(3) . . . . ?
C19 O1 B1 N2 -174.83(19) . . . . ?
C39 O2 B1 O1 -25.2(4) . . . . ?
C39 O2 B1 N1 -154.5(2) . . . . ?
C39 O2 B1 N2 91.9(3) . . . . ?
C7 N1 B1 O1 102.9(3) . . . . ?
C6 N1 B1 O1 -78.9(4) . . . . ?
C7 N1 B1 O2 -127.7(3) . . . . ?
C6 N1 B1 O2 50.5(4) . . . . ?
C7 N1 B1 N2 -9.2(4) . . . . ?
C6 N1 B1 N2 169.0(2) . . . . ?
C13 N2 B1 O1 -115.7(3) . . . . ?
C38 N2 B1 O1 63.6(3) . . . . ?
C13 N2 B1 O2 119.1(3) . . . . ?
C38 N2 B1 O2 -61.5(4) . . . . ?
C13 N2 B1 N1 5.9(4) . . . . ?
C38 N2 B1 N1 -174.7(3) . . . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_160514cm
_database_code_depnum_ccdc_archive 'CCDC 1885423'
loop_
_audit_author_name
_audit_author_address
'Chihiro MAEDA'
;Okayama University
Japan
;
_audit_update_record             
;
2018-12-17 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 B F2 N2 O'
_chemical_formula_sum            'C27 H27 B F2 N2 O'
_chemical_formula_weight         444.31

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'
F F 0.0727 0.0534 '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      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                   9.496(2)
_cell_length_b                   10.526(2)
_cell_length_c                   11.5355(16)
_cell_angle_alpha                79.482(19)
_cell_angle_beta                 77.43(3)
_cell_angle_gamma                89.68(2)
_cell_volume                     1105.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1224
_cell_measurement_theta_min      25.8
_cell_measurement_theta_max      68.1

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   0.848
_exptl_transmission_factor_max   0.971
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            14040
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.528
_diffrn_reflns_theta_max         65.996
_diffrn_reflns_theta_full        65.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             3747
_reflns_number_gt                3343
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0647P)²+0.1259P] 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         3747
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C1 C 0.05382(12) 0.03376(11) 0.77528(12) 0.0212(3) Uani 1 1 d . . . . .
H1 H 0.0962 0.1092 0.7899 0.025 Uiso 1 1 calc R U . . .
C2 C -0.05512(13) -0.03676(11) 0.86135(12) 0.0218(3) Uani 1 1 d . . . . .
H2 H -0.0859 -0.0092 0.9365 0.026 Uiso 1 1 calc R U . . .
C3 C -0.12300(12) -0.14797(11) 0.84303(11) 0.0190(3) Uani 1 1 d . . . . .
C4 C -0.07677(12) -0.18820(11) 0.73348(11) 0.0180(3) Uani 1 1 d . . . . .
H3 H -0.1215 -0.2621 0.7183 0.022 Uiso 1 1 calc R U . . .
C5 C 0.03571(12) -0.12025(10) 0.64524(11) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.09951(12) -0.00861(10) 0.66714(11) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.22156(12) -0.04071(10) 0.48917(11) 0.0169(3) Uani 1 1 d . . . . .
C8 C 0.11575(12) -0.14174(10) 0.52944(11) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.11476(12) -0.23539(10) 0.45872(11) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.0432 -0.3034 0.4842 0.021 Uiso 1 1 calc R U . . .
C10 C 0.21763(12) -0.23112(11) 0.35043(11) 0.0179(3) Uani 1 1 d . . . . .
C11 C 0.32275(12) -0.13043(11) 0.31377(11) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.3936 -0.1276 0.2411 0.022 Uiso 1 1 calc R U . . .
C12 C 0.32519(12) -0.03433(10) 0.38219(11) 0.0179(3) Uani 1 1 d . . . . .
C13 C 0.42800(12) 0.07077(10) 0.35722(11) 0.0183(3) Uani 1 1 d . . . . .
C14 C 0.54051(12) 0.24498(11) 0.37386(11) 0.0190(3) Uani 1 1 d . . . . .
C15 C 0.58783(13) 0.35467(11) 0.40719(12) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.5401 0.3837 0.4784 0.027 Uiso 1 1 calc R U . . .
C16 C 0.70921(13) 0.41932(11) 0.33003(13) 0.0259(3) Uani 1 1 d . . . . .
H7 H 0.7450 0.4957 0.3483 0.031 Uiso 1 1 calc R U . . .
C17 C 0.77961(13) 0.37553(12) 0.22711(13) 0.0268(3) Uani 1 1 d . . . . .
H8 H 0.8628 0.4227 0.1774 0.032 Uiso 1 1 calc R U . . .
C18 C 0.73323(13) 0.26504(11) 0.19372(12) 0.0239(3) Uani 1 1 d . . . . .
H9 H 0.7814 0.2345 0.1234 0.029 Uiso 1 1 calc R U . . .
C19 C 0.61151(12) 0.20353(11) 0.27121(12) 0.0205(3) Uani 1 1 d . . . . .
C20 C -0.23755(13) -0.22304(11) 0.94730(11) 0.0227(3) Uani 1 1 d . . . . .
C21 C -0.34728(14) -0.13151(13) 1.00321(14) 0.0328(3) Uani 1 1 d . . . . .
H10 H -0.2975 -0.0694 1.0356 0.049 Uiso 1 1 calc R U . . .
H11 H -0.4203 -0.1817 1.0686 0.049 Uiso 1 1 calc R U . . .
H12 H -0.3942 -0.0849 0.9411 0.049 Uiso 1 1 calc R U . . .
C22 C -0.32031(14) -0.32523(12) 0.90701(12) 0.0284(3) Uani 1 1 d . . . . .
H13 H -0.3650 -0.2837 0.8414 0.043 Uiso 1 1 calc R U . . .
H14 H -0.3955 -0.3676 0.9754 0.043 Uiso 1 1 calc R U . . .
H15 H -0.2535 -0.3898 0.8784 0.043 Uiso 1 1 calc R U . . .
C23 C -0.16080(15) -0.29235(13) 1.04391(13) 0.0311(3) Uani 1 1 d . . . . .
H16 H -0.0965 -0.3561 1.0104 0.047 Uiso 1 1 calc R U . . .
H17 H -0.2328 -0.3362 1.1140 0.047 Uiso 1 1 calc R U . . .
H18 H -0.1042 -0.2289 1.0690 0.047 Uiso 1 1 calc R U . . .
C24 C 0.22388(12) -0.33738(11) 0.27478(11) 0.0197(3) Uani 1 1 d . . . . .
C25 C 0.23624(13) -0.27939(12) 0.14098(12) 0.0248(3) Uani 1 1 d . . . . .
H19 H 0.1513 -0.2285 0.1317 0.037 Uiso 1 1 calc R U . . .
H20 H 0.2418 -0.3492 0.0945 0.037 Uiso 1 1 calc R U . . .
H21 H 0.3235 -0.2234 0.1111 0.037 Uiso 1 1 calc R U . . .
C26 C 0.35700(14) -0.41779(12) 0.28843(13) 0.0294(3) Uani 1 1 d . . . . .
H22 H 0.4433 -0.3604 0.2672 0.044 Uiso 1 1 calc R U . . .
H23 H 0.3682 -0.4809 0.2345 0.044 Uiso 1 1 calc R U . . .
H24 H 0.3444 -0.4633 0.3723 0.044 Uiso 1 1 calc R U . . .
C27 C 0.08897(14) -0.42707(13) 0.31608(13) 0.0308(3) Uani 1 1 d . . . . .
H25 H 0.0852 -0.4747 0.3981 0.046 Uiso 1 1 calc R U . . .
H26 H 0.0927 -0.4883 0.2610 0.046 Uiso 1 1 calc R U . . .
H27 H 0.0027 -0.3756 0.3156 0.046 Uiso 1 1 calc R U . . .
N1 N 0.21180(10) 0.04131(9) 0.56941(9) 0.0179(2) Uani 1 1 d . . . . .
N2 N 0.42315(10) 0.15740(9) 0.42772(9) 0.0183(2) Uani 1 1 d . . . . .
O1 O 0.53914(8) 0.09240(7) 0.26095(8) 0.0205(2) Uani 1 1 d . . . . .
B1 B 0.30194(14) 0.16675(12) 0.54521(13) 0.0201(3) Uani 1 1 d . . . . .
F1 F 0.36736(7) 0.17869(7) 0.63833(7) 0.02674(19) Uani 1 1 d . . . . .
F2 F 0.22580(7) 0.27687(6) 0.51770(7) 0.0274(2) 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
C1 C2 1.3781(18) . ?
C1 C6 1.3815(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.4101(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3860(18) . ?
C3 C20 1.5321(17) . ?
C4 C5 1.3993(17) . ?
C4 H3 0.9500 . ?
C5 C6 1.4124(16) . ?
C5 C8 1.4421(18) . ?
C6 N1 1.3967(16) . ?
C7 N1 1.3653(16) . ?
C7 C12 1.3921(18) . ?
C7 C8 1.4087(16) . ?
C8 C9 1.3909(17) . ?
C9 C10 1.4020(18) . ?
C9 H4 0.9500 . ?
C10 C11 1.4011(16) . ?
C10 C24 1.5327(17) . ?
C11 C12 1.3951(17) . ?
C11 H5 0.9500 . ?
C12 C13 1.4259(16) . ?
C13 N2 1.3225(16) . ?
C13 O1 1.3414(15) . ?
C14 C19 1.3729(19) . ?
C14 C15 1.3878(17) . ?
C14 N2 1.4067(15) . ?
C15 C16 1.3874(18) . ?
C15 H6 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H7 0.9500 . ?
C17 C18 1.3922(18) . ?
C17 H8 0.9500 . ?
C18 C19 1.3790(18) . ?
C18 H9 0.9500 . ?
C19 O1 1.3963(14) . ?
C20 C22 1.5302(17) . ?
C20 C21 1.5340(18) . ?
C20 C23 1.5350(18) . ?
C21 H10 0.9800 . ?
C21 H11 0.9800 . ?
C21 H12 0.9800 . ?
C22 H13 0.9800 . ?
C22 H14 0.9800 . ?
C22 H15 0.9800 . ?
C23 H16 0.9800 . ?
C23 H17 0.9800 . ?
C23 H18 0.9800 . ?
C24 C27 1.5307(16) . ?
C24 C25 1.5319(18) . ?
C24 C26 1.5378(17) . ?
C25 H19 0.9800 . ?
C25 H20 0.9800 . ?
C25 H21 0.9800 . ?
C26 H22 0.9800 . ?
C26 H23 0.9800 . ?
C26 H24 0.9800 . ?
C27 H25 0.9800 . ?
C27 H26 0.9800 . ?
C27 H27 0.9800 . ?
N1 B1 1.5258(15) . ?
N2 B1 1.5937(19) . ?
B1 F1 1.3770(16) . ?
B1 F2 1.3868(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.96(11) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C1 C2 C3 123.06(12) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C4 C3 C2 118.14(11) . . ?
C4 C3 C20 123.07(10) . . ?
C2 C3 C20 118.68(11) . . ?
C3 C4 C5 120.16(11) . . ?
C3 C4 H3 119.9 . . ?
C5 C4 H3 119.9 . . ?
C4 C5 C6 119.69(11) . . ?
C4 C5 C8 133.94(11) . . ?
C6 C5 C8 106.25(10) . . ?
C1 C6 N1 128.82(11) . . ?
C1 C6 C5 120.96(11) . . ?
N1 C6 C5 110.16(11) . . ?
N1 C7 C12 126.51(10) . . ?
N1 C7 C8 111.91(11) . . ?
C12 C7 C8 121.51(11) . . ?
C9 C8 C7 118.56(11) . . ?
C9 C8 C5 136.02(10) . . ?
C7 C8 C5 105.35(10) . . ?
C8 C9 C10 121.10(10) . . ?
C8 C9 H4 119.4 . . ?
C10 C9 H4 119.4 . . ?
C11 C10 C9 118.95(11) . . ?
C11 C10 C24 118.98(11) . . ?
C9 C10 C24 121.98(10) . . ?
C12 C11 C10 121.15(12) . . ?
C12 C11 H5 119.4 . . ?
C10 C11 H5 119.4 . . ?
C7 C12 C11 118.72(11) . . ?
C7 C12 C13 114.41(11) . . ?
C11 C12 C13 126.83(12) . . ?
N2 C13 O1 112.96(10) . . ?
N2 C13 C12 122.97(11) . . ?
O1 C13 C12 124.07(11) . . ?
C19 C14 C15 121.39(11) . . ?
C19 C14 N2 106.78(10) . . ?
C15 C14 N2 131.84(12) . . ?
C16 C15 C14 115.87(13) . . ?
C16 C15 H6 122.1 . . ?
C14 C15 H6 122.1 . . ?
C17 C16 C15 121.81(12) . . ?
C17 C16 H7 119.1 . . ?
C15 C16 H7 119.1 . . ?
C16 C17 C18 122.55(12) . . ?
C16 C17 H8 118.7 . . ?
C18 C17 H8 118.7 . . ?
C19 C18 C17 114.42(13) . . ?
C19 C18 H9 122.8 . . ?
C17 C18 H9 122.8 . . ?
C14 C19 C18 123.94(11) . . ?
C14 C19 O1 108.44(10) . . ?
C18 C19 O1 127.61(12) . . ?
C22 C20 C3 112.34(11) . . ?
C22 C20 C21 108.08(10) . . ?
C3 C20 C21 110.93(10) . . ?
C22 C20 C23 108.07(10) . . ?
C3 C20 C23 108.12(10) . . ?
C21 C20 C23 109.23(11) . . ?
C20 C21 H10 109.5 . . ?
C20 C21 H11 109.5 . . ?
H10 C21 H11 109.5 . . ?
C20 C21 H12 109.5 . . ?
H10 C21 H12 109.5 . . ?
H11 C21 H12 109.5 . . ?
C20 C22 H13 109.5 . . ?
C20 C22 H14 109.5 . . ?
H13 C22 H14 109.5 . . ?
C20 C22 H15 109.5 . . ?
H13 C22 H15 109.5 . . ?
H14 C22 H15 109.5 . . ?
C20 C23 H16 109.5 . . ?
C20 C23 H17 109.5 . . ?
H16 C23 H17 109.5 . . ?
C20 C23 H18 109.5 . . ?
H16 C23 H18 109.5 . . ?
H17 C23 H18 109.5 . . ?
C27 C24 C25 107.51(10) . . ?
C27 C24 C10 111.88(10) . . ?
C25 C24 C10 111.12(9) . . ?
C27 C24 C26 108.83(10) . . ?
C25 C24 C26 109.13(11) . . ?
C10 C24 C26 108.32(10) . . ?
C24 C25 H19 109.5 . . ?
C24 C25 H20 109.5 . . ?
H19 C25 H20 109.5 . . ?
C24 C25 H21 109.5 . . ?
H19 C25 H21 109.5 . . ?
H20 C25 H21 109.5 . . ?
C24 C26 H22 109.5 . . ?
C24 C26 H23 109.5 . . ?
H22 C26 H23 109.5 . . ?
C24 C26 H24 109.5 . . ?
H22 C26 H24 109.5 . . ?
H23 C26 H24 109.5 . . ?
C24 C27 H25 109.5 . . ?
C24 C27 H26 109.5 . . ?
H25 C27 H26 109.5 . . ?
C24 C27 H27 109.5 . . ?
H25 C27 H27 109.5 . . ?
H26 C27 H27 109.5 . . ?
C7 N1 C6 106.30(9) . . ?
C7 N1 B1 123.93(10) . . ?
C6 N1 B1 129.59(10) . . ?
C13 N2 C14 106.44(10) . . ?
C13 N2 B1 126.78(10) . . ?
C14 N2 B1 126.64(10) . . ?
C13 O1 C19 105.38(9) . . ?
F1 B1 F2 109.36(10) . . ?
F1 B1 N1 112.91(10) . . ?
F2 B1 N1 113.67(10) . . ?
F1 B1 N2 109.08(9) . . ?
F2 B1 N2 107.26(10) . . ?
N1 B1 N2 104.22(10) . . ?

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 C1 C2 C3 -1.14(17) . . . . ?
C1 C2 C3 C4 0.47(17) . . . . ?
C1 C2 C3 C20 176.87(10) . . . . ?
C2 C3 C4 C5 0.91(16) . . . . ?
C20 C3 C4 C5 -175.32(10) . . . . ?
C3 C4 C5 C6 -1.56(16) . . . . ?
C3 C4 C5 C8 173.82(11) . . . . ?
C2 C1 C6 N1 -176.26(10) . . . . ?
C2 C1 C6 C5 0.46(16) . . . . ?
C4 C5 C6 C1 0.87(16) . . . . ?
C8 C5 C6 C1 -175.67(10) . . . . ?
C4 C5 C6 N1 178.15(9) . . . . ?
C8 C5 C6 N1 1.61(12) . . . . ?
N1 C7 C8 C9 -178.16(9) . . . . ?
C12 C7 C8 C9 -1.05(16) . . . . ?
N1 C7 C8 C5 -0.81(12) . . . . ?
C12 C7 C8 C5 176.29(10) . . . . ?
C4 C5 C8 C9 0.3(2) . . . . ?
C6 C5 C8 C9 176.15(12) . . . . ?
C4 C5 C8 C7 -176.32(11) . . . . ?
C6 C5 C8 C7 -0.49(11) . . . . ?
C7 C8 C9 C10 0.88(15) . . . . ?
C5 C8 C9 C10 -175.43(12) . . . . ?
C8 C9 C10 C11 0.04(16) . . . . ?
C8 C9 C10 C24 176.45(10) . . . . ?
C9 C10 C11 C12 -0.84(16) . . . . ?
C24 C10 C11 C12 -177.36(10) . . . . ?
N1 C7 C12 C11 176.94(10) . . . . ?
C8 C7 C12 C11 0.28(16) . . . . ?
N1 C7 C12 C13 -0.74(16) . . . . ?
C8 C7 C12 C13 -177.40(9) . . . . ?
C10 C11 C12 C7 0.68(16) . . . . ?
C10 C11 C12 C13 178.05(10) . . . . ?
C7 C12 C13 N2 -1.91(16) . . . . ?
C11 C12 C13 N2 -179.38(10) . . . . ?
C7 C12 C13 O1 177.96(9) . . . . ?
C11 C12 C13 O1 0.49(18) . . . . ?
C19 C14 C15 C16 0.64(16) . . . . ?
N2 C14 C15 C16 -179.31(11) . . . . ?
C14 C15 C16 C17 -0.91(17) . . . . ?
C15 C16 C17 C18 0.49(18) . . . . ?
C16 C17 C18 C19 0.24(17) . . . . ?
C15 C14 C19 C18 0.08(18) . . . . ?
N2 C14 C19 C18 -179.96(10) . . . . ?
C15 C14 C19 O1 -179.64(10) . . . . ?
N2 C14 C19 O1 0.32(12) . . . . ?
C17 C18 C19 C14 -0.52(16) . . . . ?
C17 C18 C19 O1 179.15(10) . . . . ?
C4 C3 C20 C22 -14.32(15) . . . . ?
C2 C3 C20 C22 169.46(10) . . . . ?
C4 C3 C20 C21 -135.42(12) . . . . ?
C2 C3 C20 C21 48.37(14) . . . . ?
C4 C3 C20 C23 104.83(13) . . . . ?
C2 C3 C20 C23 -71.38(13) . . . . ?
C11 C10 C24 C27 -171.10(10) . . . . ?
C9 C10 C24 C27 12.49(15) . . . . ?
C11 C10 C24 C25 -50.93(14) . . . . ?
C9 C10 C24 C25 132.66(11) . . . . ?
C11 C10 C24 C26 68.95(13) . . . . ?
C9 C10 C24 C26 -107.47(12) . . . . ?
C12 C7 N1 C6 -175.14(10) . . . . ?
C8 C7 N1 C6 1.79(12) . . . . ?
C12 C7 N1 B1 9.29(17) . . . . ?
C8 C7 N1 B1 -173.79(10) . . . . ?
C1 C6 N1 C7 174.91(11) . . . . ?
C5 C6 N1 C7 -2.09(12) . . . . ?
C1 C6 N1 B1 -9.85(19) . . . . ?
C5 C6 N1 B1 173.14(10) . . . . ?
O1 C13 N2 C14 0.35(12) . . . . ?
C12 C13 N2 C14 -179.77(10) . . . . ?
O1 C13 N2 B1 176.32(9) . . . . ?
C12 C13 N2 B1 -3.80(17) . . . . ?
C19 C14 N2 C13 -0.40(12) . . . . ?
C15 C14 N2 C13 179.55(12) . . . . ?
C19 C14 N2 B1 -176.38(10) . . . . ?
C15 C14 N2 B1 3.58(19) . . . . ?
N2 C13 O1 C19 -0.15(12) . . . . ?
C12 C13 O1 C19 179.97(10) . . . . ?
C14 C19 O1 C13 -0.12(11) . . . . ?
C18 C19 O1 C13 -179.83(11) . . . . ?
C7 N1 B1 F1 -130.52(11) . . . . ?
C6 N1 B1 F1 55.00(15) . . . . ?
C7 N1 B1 F2 104.16(13) . . . . ?
C6 N1 B1 F2 -70.33(16) . . . . ?
C7 N1 B1 N2 -12.28(14) . . . . ?
C6 N1 B1 N2 173.23(10) . . . . ?
C13 N2 B1 F1 130.93(11) . . . . ?
C14 N2 B1 F1 -53.89(14) . . . . ?
C13 N2 B1 F2 -110.74(12) . . . . ?
C14 N2 B1 F2 64.44(14) . . . . ?
C13 N2 B1 N1 10.09(15) . . . . ?
C14 N2 B1 N1 -174.73(9) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_70603cm3
_database_code_depnum_ccdc_archive 'CCDC 1885422'
loop_
_audit_author_name
_audit_author_address
'Chihiro MAEDA'
;Okayama University
Japan
;
_audit_update_record             
;
2018-12-17 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H23 B N2 O3'
_chemical_formula_sum            'C39 H23 B N2 O3'
_chemical_formula_weight         578.40

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      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                   13.000(3)
_cell_length_b                   6.5948(15)
_cell_length_c                   16.243(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.955(6)
_cell_angle_gamma                90
_cell_volume                     1389.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1162
_cell_measurement_theta_min      31.4
_cell_measurement_theta_max      68.2

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.694
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            18079
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.639
_diffrn_reflns_theta_max         68.045
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_point_group_measured_fraction_full 0.861
_reflns_number_total             4347
_reflns_number_gt                3959
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_max     0.716
_reflns_Friedel_fraction_full    0.716

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1037P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1343 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4347
_refine_ls_number_parameters     406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1407
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
O2 O 0.32527(16) 0.3347(4) 0.30738(13) 0.0361(6) Uani 1 1 d . . . . .
O1 O 0.60086(14) 0.5176(4) 0.46620(12) 0.0364(5) Uani 1 1 d . . . . .
O3 O 0.30853(16) 0.7045(4) 0.30380(12) 0.0345(6) Uani 1 1 d . . . . .
N1 N 0.45809(18) 0.5241(5) 0.38056(15) 0.0337(6) Uani 1 1 d . . . . .
N2 N 0.28217(17) 0.5419(5) 0.43138(14) 0.0333(6) Uani 1 1 d . . . . .
C24 C 0.3173(2) 0.7148(6) 0.22078(18) 0.0352(8) Uani 1 1 d . . . . .
C25 C 0.4965(2) 0.5190(6) 0.45827(17) 0.0334(7) Uani 1 1 d . . . . .
C26 C 0.5437(2) 0.5224(6) 0.33172(18) 0.0342(7) Uani 1 1 d . . . . .
C27 C 0.6309(2) 0.5212(6) 0.38529(18) 0.0360(7) Uani 1 1 d . . . . .
C28 C 0.5527(2) 0.5183(6) 0.24736(19) 0.0374(7) Uani 1 1 d . . . . .
H1 H 0.4941 0.5154 0.2091 0.045 Uiso 1 1 calc R U . . .
C29 C 0.2325(2) 0.2992(6) 0.26434(19) 0.0365(8) Uani 1 1 d . . . . .
C30 C 0.2597(2) 0.5491(5) 0.56987(18) 0.0336(7) Uani 1 1 d . . . . .
C31 C 0.1720(3) 0.1372(6) 0.2898(2) 0.0405(8) Uani 1 1 d . . . . .
H2 H 0.1964 0.0540 0.3348 0.049 Uiso 1 1 calc R U . . .
C32 C 0.1615(2) 0.5840(5) 0.5270(2) 0.0368(8) Uani 1 1 d . . . . .
C33 C 0.2736(2) 0.5722(6) 0.16714(18) 0.0359(8) Uani 1 1 d . . . . .
C34 C 0.3695(2) 0.8864(6) 0.1921(2) 0.0386(8) Uani 1 1 d . . . . .
H3 H 0.3911 0.9920 0.2292 0.046 Uiso 1 1 calc R U . . .
C35 C 0.1772(2) 0.5788(5) 0.44235(19) 0.0344(8) Uani 1 1 d . . . . .
C36 C 0.4369(2) 0.5157(6) 0.52779(17) 0.0339(7) Uani 1 1 d . . . . .
C37 C 0.3302(2) 0.5302(6) 0.50887(18) 0.0340(7) Uani 1 1 d . . . . .
C38 C 0.6529(3) 0.5188(7) 0.2220(2) 0.0427(8) Uani 1 1 d . . . . .
H4 H 0.6627 0.5175 0.1645 0.051 Uiso 1 1 calc R U . . .
C39 C 0.0966(2) 0.6108(6) 0.3826(2) 0.0377(8) Uani 1 1 d . . . . .
H5 H 0.1071 0.6075 0.3253 0.045 Uiso 1 1 calc R U . . .
C40 C 0.0783(3) 0.0998(6) 0.2498(2) 0.0452(9) Uani 1 1 d . . . . .
H6 H 0.0392 -0.0140 0.2653 0.054 Uiso 1 1 calc R U . . .
C41 C 0.3008(2) 0.5765(6) 0.08319(19) 0.0409(9) Uani 1 1 d . . . . .
C42 C 0.4741(2) 0.5101(6) 0.61004(18) 0.0381(8) Uani 1 1 d . . . . .
H7 H 0.5461 0.5009 0.6240 0.046 Uiso 1 1 calc R U . . .
C43 C 0.1001(2) 0.3893(6) 0.15901(19) 0.0400(9) Uani 1 1 d . . . . .
C44 C 0.0001(2) 0.6477(6) 0.4112(2) 0.0394(8) Uani 1 1 d . . . . .
H8 H -0.0567 0.6698 0.3723 0.047 Uiso 1 1 calc R U . . .
C45 C 0.3887(2) 0.8990(7) 0.1103(2) 0.0444(10) Uani 1 1 d . . . . .
H9 H 0.4220 1.0158 0.0907 0.053 Uiso 1 1 calc R U . . .
C46 C 0.3599(2) 0.7422(7) 0.0554(2) 0.0438(9) Uani 1 1 d . . . . .
C47 C -0.0161(3) 0.6532(6) 0.4950(2) 0.0391(8) Uani 1 1 d . . . . .
H10 H -0.0835 0.6777 0.5119 0.047 Uiso 1 1 calc R U . . .
C48 C 0.2028(2) 0.4157(6) 0.19727(19) 0.0368(8) Uani 1 1 d . . . . .
C49 C 0.7394(2) 0.5212(7) 0.2779(2) 0.0427(8) Uani 1 1 d . . . . .
H11 H 0.8061 0.5234 0.2574 0.051 Uiso 1 1 calc R U . . .
C50 C 0.7308(2) 0.5205(7) 0.3620(2) 0.0415(8) Uani 1 1 d . . . . .
H12 H 0.7890 0.5196 0.4007 0.050 Uiso 1 1 calc R U . . .
C51 C 0.0384(2) 0.2276(7) 0.1855(2) 0.0437(9) Uani 1 1 d . . . . .
C52 C 0.0570(2) 0.5249(8) 0.09798(19) 0.0457(9) Uani 1 1 d . . . . .
H13 H 0.0966 0.6365 0.0810 0.055 Uiso 1 1 calc R U . . .
C53 C 0.0636(2) 0.6241(5) 0.5533(2) 0.0372(8) Uani 1 1 d . . . . .
H14 H 0.0526 0.6310 0.6104 0.045 Uiso 1 1 calc R U . . .
C54 C 0.2729(2) 0.4175(7) 0.0270(2) 0.0481(10) Uani 1 1 d . . . . .
H15 H 0.2344 0.3050 0.0446 0.058 Uiso 1 1 calc R U . . .
C55 C 0.4046(3) 0.5182(7) 0.67221(19) 0.0431(8) Uani 1 1 d . . . . .
H16 H 0.4302 0.5096 0.7283 0.052 Uiso 1 1 calc R U . . .
C56 C 0.2998(3) 0.5382(7) 0.65373(19) 0.0421(8) Uani 1 1 d . . . . .
H17 H 0.2543 0.5448 0.6970 0.051 Uiso 1 1 calc R U . . .
C57 C 0.3888(3) 0.7445(8) -0.0275(2) 0.0536(11) Uani 1 1 d . . . . .
H18 H 0.4289 0.8533 -0.0463 0.064 Uiso 1 1 calc R U . . .
C58 C -0.0631(3) 0.2022(8) 0.1471(2) 0.0544(11) Uani 1 1 d . . . . .
H19 H -0.1048 0.0932 0.1635 0.065 Uiso 1 1 calc R U . . .
C59 C 0.3592(3) 0.5913(8) -0.0794(2) 0.0590(13) Uani 1 1 d . . . . .
H20 H 0.3777 0.5956 -0.1350 0.071 Uiso 1 1 calc R U . . .
C60 C -0.1003(3) 0.3304(8) 0.0879(2) 0.0573(12) Uani 1 1 d . . . . .
H21 H -0.1674 0.3090 0.0623 0.069 Uiso 1 1 calc R U . . .
C61 C -0.0411(2) 0.4965(9) 0.0632(2) 0.0545(12) Uani 1 1 d . . . . .
H22 H -0.0691 0.5884 0.0226 0.065 Uiso 1 1 calc R U . . .
C62 C 0.3016(3) 0.4263(8) -0.0529(2) 0.0541(11) Uani 1 1 d . . . . .
H23 H 0.2824 0.3201 -0.0904 0.065 Uiso 1 1 calc R U . . .
B1 B 0.3378(2) 0.5250(7) 0.3505(2) 0.0332(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
O2 C29 1.372(4) . ?
O2 B1 1.441(5) . ?
O1 C25 1.355(3) . ?
O1 C27 1.397(3) . ?
O3 C24 1.363(4) . ?
O3 B1 1.443(5) . ?
N1 C25 1.325(4) . ?
N1 C26 1.411(4) . ?
N1 B1 1.606(4) . ?
N2 C37 1.368(4) . ?
N2 C35 1.409(4) . ?
N2 B1 1.547(4) . ?
C24 C33 1.377(5) . ?
C24 C34 1.415(5) . ?
C25 C36 1.413(4) . ?
C26 C27 1.381(4) . ?
C26 C28 1.384(4) . ?
C27 C50 1.377(4) . ?
C28 C38 1.393(4) . ?
C28 H1 0.9500 . ?
C29 C48 1.366(5) . ?
C29 C31 1.405(5) . ?
C30 C37 1.401(4) . ?
C30 C56 1.426(4) . ?
C30 C32 1.431(5) . ?
C31 C40 1.364(5) . ?
C31 H2 0.9500 . ?
C32 C53 1.395(5) . ?
C32 C35 1.404(4) . ?
C33 C41 1.432(4) . ?
C33 C48 1.488(5) . ?
C34 C45 1.371(5) . ?
C34 H3 0.9500 . ?
C35 C39 1.395(4) . ?
C36 C42 1.390(4) . ?
C36 C37 1.403(4) . ?
C38 C49 1.396(5) . ?
C38 H4 0.9500 . ?
C39 C44 1.388(4) . ?
C39 H5 0.9500 . ?
C40 C51 1.411(5) . ?
C40 H6 0.9500 . ?
C41 C54 1.420(5) . ?
C41 C46 1.427(6) . ?
C42 C55 1.401(4) . ?
C42 H7 0.9500 . ?
C43 C51 1.419(5) . ?
C43 C52 1.421(6) . ?
C43 C48 1.444(4) . ?
C44 C47 1.391(5) . ?
C44 H8 0.9500 . ?
C45 C46 1.400(6) . ?
C45 H9 0.9500 . ?
C46 C57 1.422(5) . ?
C47 C53 1.369(5) . ?
C47 H10 0.9500 . ?
C49 C50 1.378(4) . ?
C49 H11 0.9500 . ?
C50 H12 0.9500 . ?
C51 C58 1.431(5) . ?
C52 C61 1.371(4) . ?
C52 H13 0.9500 . ?
C53 H14 0.9500 . ?
C54 C62 1.376(5) . ?
C54 H15 0.9500 . ?
C55 C56 1.381(5) . ?
C55 H16 0.9500 . ?
C56 H17 0.9500 . ?
C57 C59 1.355(7) . ?
C57 H18 0.9500 . ?
C58 C60 1.345(6) . ?
C58 H19 0.9500 . ?
C59 C62 1.405(7) . ?
C59 H20 0.9500 . ?
C60 C61 1.413(7) . ?
C60 H21 0.9500 . ?
C61 H22 0.9500 . ?
C62 H23 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
C29 O2 B1 117.5(3) . . ?
C25 O1 C27 104.7(2) . . ?
C24 O3 B1 121.6(3) . . ?
C25 N1 C26 106.0(2) . . ?
C25 N1 B1 125.8(2) . . ?
C26 N1 B1 128.2(2) . . ?
C37 N2 C35 106.1(2) . . ?
C37 N2 B1 124.6(2) . . ?
C35 N2 B1 129.3(2) . . ?
O3 C24 C33 122.2(3) . . ?
O3 C24 C34 116.1(3) . . ?
C33 C24 C34 121.6(3) . . ?
N1 C25 O1 113.6(3) . . ?
N1 C25 C36 124.8(3) . . ?
O1 C25 C36 121.6(3) . . ?
C27 C26 C28 120.2(3) . . ?
C27 C26 N1 106.9(3) . . ?
C28 C26 N1 132.9(3) . . ?
C50 C27 C26 125.1(3) . . ?
C50 C27 O1 126.1(3) . . ?
C26 C27 O1 108.8(2) . . ?
C26 C28 C38 116.0(3) . . ?
C26 C28 H1 122.0 . . ?
C38 C28 H1 122.0 . . ?
C48 C29 O2 120.0(3) . . ?
C48 C29 C31 122.0(3) . . ?
O2 C29 C31 118.0(3) . . ?
C37 C30 C56 117.2(3) . . ?
C37 C30 C32 106.0(3) . . ?
C56 C30 C32 136.7(3) . . ?
C40 C31 C29 119.7(3) . . ?
C40 C31 H2 120.1 . . ?
C29 C31 H2 120.1 . . ?
C53 C32 C35 120.1(3) . . ?
C53 C32 C30 133.1(3) . . ?
C35 C32 C30 106.7(3) . . ?
C24 C33 C41 118.1(3) . . ?
C24 C33 C48 120.2(3) . . ?
C41 C33 C48 121.7(3) . . ?
C45 C34 C24 119.4(4) . . ?
C45 C34 H3 120.3 . . ?
C24 C34 H3 120.3 . . ?
C39 C35 C32 121.6(3) . . ?
C39 C35 N2 128.8(3) . . ?
C32 C35 N2 109.6(3) . . ?
C42 C36 C37 119.0(3) . . ?
C42 C36 C25 126.6(3) . . ?
C37 C36 C25 114.3(3) . . ?
N2 C37 C30 111.5(3) . . ?
N2 C37 C36 125.9(3) . . ?
C30 C37 C36 122.4(3) . . ?
C28 C38 C49 122.3(3) . . ?
C28 C38 H4 118.8 . . ?
C49 C38 H4 118.8 . . ?
C44 C39 C35 116.5(3) . . ?
C44 C39 H5 121.7 . . ?
C35 C39 H5 121.7 . . ?
C31 C40 C51 121.0(4) . . ?
C31 C40 H6 119.5 . . ?
C51 C40 H6 119.5 . . ?
C54 C41 C46 118.8(3) . . ?
C54 C41 C33 121.9(3) . . ?
C46 C41 C33 119.3(3) . . ?
C36 C42 C55 119.6(3) . . ?
C36 C42 H7 120.2 . . ?
C55 C42 H7 120.2 . . ?
C51 C43 C52 118.8(3) . . ?
C51 C43 C48 119.0(3) . . ?
C52 C43 C48 122.2(3) . . ?
C39 C44 C47 122.2(3) . . ?
C39 C44 H8 118.9 . . ?
C47 C44 H8 118.9 . . ?
C34 C45 C46 121.0(4) . . ?
C34 C45 H9 119.5 . . ?
C46 C45 H9 119.5 . . ?
C45 C46 C57 121.2(4) . . ?
C45 C46 C41 119.3(3) . . ?
C57 C46 C41 119.4(4) . . ?
C53 C47 C44 121.0(3) . . ?
C53 C47 H10 119.5 . . ?
C44 C47 H10 119.5 . . ?
C29 C48 C43 118.5(3) . . ?
C29 C48 C33 120.3(3) . . ?
C43 C48 C33 121.1(3) . . ?
C50 C49 C38 121.9(3) . . ?
C50 C49 H11 119.1 . . ?
C38 C49 H11 119.1 . . ?
C27 C50 C49 114.6(3) . . ?
C27 C50 H12 122.7 . . ?
C49 C50 H12 122.7 . . ?
C40 C51 C43 119.1(3) . . ?
C40 C51 C58 122.3(4) . . ?
C43 C51 C58 118.6(4) . . ?
C61 C52 C43 120.8(4) . . ?
C61 C52 H13 119.6 . . ?
C43 C52 H13 119.6 . . ?
C47 C53 C32 118.5(3) . . ?
C47 C53 H14 120.7 . . ?
C32 C53 H14 120.7 . . ?
C62 C54 C41 120.0(4) . . ?
C62 C54 H15 120.0 . . ?
C41 C54 H15 120.0 . . ?
C56 C55 C42 121.5(3) . . ?
C56 C55 H16 119.3 . . ?
C42 C55 H16 119.3 . . ?
C55 C56 C30 120.2(3) . . ?
C55 C56 H17 119.9 . . ?
C30 C56 H17 119.9 . . ?
C59 C57 C46 119.9(4) . . ?
C59 C57 H18 120.0 . . ?
C46 C57 H18 120.0 . . ?
C60 C58 C51 121.0(4) . . ?
C60 C58 H19 119.5 . . ?
C51 C58 H19 119.5 . . ?
C57 C59 C62 121.4(3) . . ?
C57 C59 H20 119.3 . . ?
C62 C59 H20 119.3 . . ?
C58 C60 C61 120.9(3) . . ?
C58 C60 H21 119.6 . . ?
C61 C60 H21 119.6 . . ?
C52 C61 C60 119.9(4) . . ?
C52 C61 H22 120.0 . . ?
C60 C61 H22 120.0 . . ?
C54 C62 C59 120.4(4) . . ?
C54 C62 H23 119.8 . . ?
C59 C62 H23 119.8 . . ?
O2 B1 O3 116.3(2) . . ?
O2 B1 N2 115.6(3) . . ?
O3 B1 N2 105.4(3) . . ?
O2 B1 N1 102.7(3) . . ?
O3 B1 N1 112.2(3) . . ?
N2 B1 N1 104.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 O3 C24 C33 53.9(4) . . . . ?
B1 O3 C24 C34 -129.2(3) . . . . ?
C26 N1 C25 O1 1.1(4) . . . . ?
B1 N1 C25 O1 179.4(3) . . . . ?
C26 N1 C25 C36 -179.0(4) . . . . ?
B1 N1 C25 C36 -0.7(6) . . . . ?
C27 O1 C25 N1 -0.3(4) . . . . ?
C27 O1 C25 C36 179.8(4) . . . . ?
C25 N1 C26 C27 -1.5(4) . . . . ?
B1 N1 C26 C27 -179.7(3) . . . . ?
C25 N1 C26 C28 177.3(4) . . . . ?
B1 N1 C26 C28 -1.0(7) . . . . ?
C28 C26 C27 C50 1.4(6) . . . . ?
N1 C26 C27 C50 -179.6(4) . . . . ?
C28 C26 C27 O1 -177.6(4) . . . . ?
N1 C26 C27 O1 1.3(4) . . . . ?
C25 O1 C27 C50 -179.7(4) . . . . ?
C25 O1 C27 C26 -0.7(4) . . . . ?
C27 C26 C28 C38 -1.7(6) . . . . ?
N1 C26 C28 C38 179.7(4) . . . . ?
B1 O2 C29 C48 65.6(4) . . . . ?
B1 O2 C29 C31 -116.5(3) . . . . ?
C48 C29 C31 C40 -3.6(5) . . . . ?
O2 C29 C31 C40 178.6(3) . . . . ?
C37 C30 C32 C53 -176.3(4) . . . . ?
C56 C30 C32 C53 0.7(7) . . . . ?
C37 C30 C32 C35 1.6(4) . . . . ?
C56 C30 C32 C35 178.6(4) . . . . ?
O3 C24 C33 C41 -170.0(3) . . . . ?
C34 C24 C33 C41 13.3(5) . . . . ?
O3 C24 C33 C48 8.3(5) . . . . ?
C34 C24 C33 C48 -168.4(3) . . . . ?
O3 C24 C34 C45 174.7(3) . . . . ?
C33 C24 C34 C45 -8.4(5) . . . . ?
C53 C32 C35 C39 -0.8(5) . . . . ?
C30 C32 C35 C39 -179.0(3) . . . . ?
C53 C32 C35 N2 178.2(3) . . . . ?
C30 C32 C35 N2 0.0(4) . . . . ?
C37 N2 C35 C39 177.3(4) . . . . ?
B1 N2 C35 C39 -0.4(6) . . . . ?
C37 N2 C35 C32 -1.6(4) . . . . ?
B1 N2 C35 C32 -179.3(3) . . . . ?
N1 C25 C36 C42 179.9(4) . . . . ?
O1 C25 C36 C42 -0.2(6) . . . . ?
N1 C25 C36 C37 -3.6(6) . . . . ?
O1 C25 C36 C37 176.3(3) . . . . ?
C35 N2 C37 C30 2.7(4) . . . . ?
B1 N2 C37 C30 -179.5(3) . . . . ?
C35 N2 C37 C36 -173.1(4) . . . . ?
B1 N2 C37 C36 4.8(6) . . . . ?
C56 C30 C37 N2 179.6(3) . . . . ?
C32 C30 C37 N2 -2.7(4) . . . . ?
C56 C30 C37 C36 -4.5(5) . . . . ?
C32 C30 C37 C36 173.2(3) . . . . ?
C42 C36 C37 N2 178.4(4) . . . . ?
C25 C36 C37 N2 1.6(5) . . . . ?
C42 C36 C37 C30 3.1(6) . . . . ?
C25 C36 C37 C30 -173.7(4) . . . . ?
C26 C28 C38 C49 0.6(6) . . . . ?
C32 C35 C39 C44 -0.1(5) . . . . ?
N2 C35 C39 C44 -178.8(4) . . . . ?
C29 C31 C40 C51 -3.2(5) . . . . ?
C24 C33 C41 C54 169.8(3) . . . . ?
C48 C33 C41 C54 -8.4(5) . . . . ?
C24 C33 C41 C46 -8.5(4) . . . . ?
C48 C33 C41 C46 173.3(3) . . . . ?
C37 C36 C42 C55 0.3(6) . . . . ?
C25 C36 C42 C55 176.7(4) . . . . ?
C35 C39 C44 C47 0.2(5) . . . . ?
C24 C34 C45 C46 -1.7(5) . . . . ?
C34 C45 C46 C57 -173.5(3) . . . . ?
C34 C45 C46 C41 6.2(5) . . . . ?
C54 C41 C46 C45 -179.4(3) . . . . ?
C33 C41 C46 C45 -1.0(5) . . . . ?
C54 C41 C46 C57 0.3(5) . . . . ?
C33 C41 C46 C57 178.6(3) . . . . ?
C39 C44 C47 C53 0.6(6) . . . . ?
O2 C29 C48 C43 -173.2(3) . . . . ?
C31 C29 C48 C43 9.0(5) . . . . ?
O2 C29 C48 C33 4.0(5) . . . . ?
C31 C29 C48 C33 -173.8(3) . . . . ?
C51 C43 C48 C29 -7.8(5) . . . . ?
C52 C43 C48 C29 169.6(3) . . . . ?
C51 C43 C48 C33 175.0(3) . . . . ?
C52 C43 C48 C33 -7.6(5) . . . . ?
C24 C33 C48 C29 -52.3(5) . . . . ?
C41 C33 C48 C29 125.9(3) . . . . ?
C24 C33 C48 C43 124.9(3) . . . . ?
C41 C33 C48 C43 -57.0(4) . . . . ?
C28 C38 C49 C50 0.9(7) . . . . ?
C26 C27 C50 C49 0.0(6) . . . . ?
O1 C27 C50 C49 178.9(4) . . . . ?
C38 C49 C50 C27 -1.2(6) . . . . ?
C31 C40 C51 C43 4.1(5) . . . . ?
C31 C40 C51 C58 -174.7(3) . . . . ?
C52 C43 C51 C40 -176.1(3) . . . . ?
C48 C43 C51 C40 1.4(5) . . . . ?
C52 C43 C51 C58 2.8(5) . . . . ?
C48 C43 C51 C58 -179.8(3) . . . . ?
C51 C43 C52 C61 -2.2(5) . . . . ?
C48 C43 C52 C61 -179.5(3) . . . . ?
C44 C47 C53 C32 -1.4(5) . . . . ?
C35 C32 C53 C47 1.5(5) . . . . ?
C30 C32 C53 C47 179.2(4) . . . . ?
C46 C41 C54 C62 -0.9(5) . . . . ?
C33 C41 C54 C62 -179.2(3) . . . . ?
C36 C42 C55 C56 -2.1(6) . . . . ?
C42 C55 C56 C30 0.7(6) . . . . ?
C37 C30 C56 C55 2.5(6) . . . . ?
C32 C30 C56 C55 -174.2(4) . . . . ?
C45 C46 C57 C59 -179.5(3) . . . . ?
C41 C46 C57 C59 0.8(5) . . . . ?
C40 C51 C58 C60 177.8(4) . . . . ?
C43 C51 C58 C60 -1.1(5) . . . . ?
C46 C57 C59 C62 -1.3(6) . . . . ?
C51 C58 C60 C61 -1.4(6) . . . . ?
C43 C52 C61 C60 -0.2(6) . . . . ?
C58 C60 C61 C52 2.0(6) . . . . ?
C41 C54 C62 C59 0.4(5) . . . . ?
C57 C59 C62 C54 0.7(6) . . . . ?
C29 O2 B1 O3 -48.9(3) . . . . ?
C29 O2 B1 N2 75.5(3) . . . . ?
C29 O2 B1 N1 -171.8(2) . . . . ?
C24 O3 B1 O2 -30.9(4) . . . . ?
C24 O3 B1 N2 -160.4(2) . . . . ?
C24 O3 B1 N1 86.8(3) . . . . ?
C37 N2 B1 O2 104.2(4) . . . . ?
C35 N2 B1 O2 -78.5(4) . . . . ?
C37 N2 B1 O3 -125.9(3) . . . . ?
C35 N2 B1 O3 51.4(5) . . . . ?
C37 N2 B1 N1 -7.6(5) . . . . ?
C35 N2 B1 N1 169.7(3) . . . . ?
C25 N1 B1 O2 -115.0(4) . . . . ?
C26 N1 B1 O2 62.9(4) . . . . ?
C25 N1 B1 O3 119.4(4) . . . . ?
C26 N1 B1 O3 -62.7(5) . . . . ?
C25 N1 B1 N2 5.8(5) . . . . ?
C26 N1 B1 N2 -176.2(3) . . . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.073



