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

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1848439'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        EE
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 B N O2'
_chemical_formula_weight         313.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'Cc   '

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

_cell_length_a                   10.1937(12)
_cell_length_b                   24.9479(16)
_cell_length_c                   7.566(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.872(17)
_cell_angle_gamma                90.00
_cell_volume                     1668.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1128
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      22.98

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4093
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2693
_reflns_number_gt                1941
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0179(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2693
_refine_ls_number_parameters     218
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.035
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0744(3) 0.88098(10) 0.9409(3) 0.0563(7) Uani 1 1 d . . .
O1 O -0.0565(3) 0.68809(10) 0.2771(4) 0.0916(9) Uani 1 1 d . . .
O2 O -0.1483(4) 0.75810(11) 0.0597(3) 0.0967(9) Uani 1 1 d . . .
B1 B -0.0803(5) 0.74124(16) 0.2563(6) 0.0620(10) Uani 1 1 d . . .
C1 C -0.1169(7) 0.6652(2) 0.0763(7) 0.1253(19) Uani 1 1 d . . .
H1A H -0.1984 0.6404 0.0481 0.150 Uiso 1 1 calc R . .
H1B H -0.0387 0.6461 0.0644 0.150 Uiso 1 1 calc R . .
C2 C -0.1746(6) 0.7120(2) -0.0689(6) 0.1024(15) Uani 1 1 d . . .
H2A H -0.1197 0.7152 -0.1426 0.123 Uiso 1 1 calc R . .
H2B H -0.2815 0.7080 -0.1662 0.123 Uiso 1 1 calc R . .
C3 C -0.0389(4) 0.77879(13) 0.4386(4) 0.0579(8) Uani 1 1 d . . .
C4 C 0.0443(4) 0.76054(14) 0.6382(5) 0.0664(9) Uani 1 1 d . . .
H4A H 0.0759 0.7250 0.6616 0.080 Uiso 1 1 calc R . .
C5 C 0.0815(4) 0.79368(13) 0.8030(4) 0.0623(9) Uani 1 1 d . . .
H5A H 0.1375 0.7804 0.9350 0.075 Uiso 1 1 calc R . .
C6 C 0.0356(3) 0.84621(12) 0.7717(4) 0.0516(8) Uani 1 1 d . . .
C7 C -0.0481(4) 0.86523(13) 0.5760(5) 0.0735(10) Uani 1 1 d . . .
H7A H -0.0806 0.9007 0.5537 0.088 Uiso 1 1 calc R . .
C8 C -0.0841(4) 0.83193(13) 0.4120(5) 0.0751(11) Uani 1 1 d . . .
H8A H -0.1401 0.8455 0.2805 0.090 Uiso 1 1 calc R . .
C9 C 0.2197(4) 0.89976(12) 1.0733(4) 0.0568(8) Uani 1 1 d . . .
C10 C 0.3553(4) 0.88759(14) 1.0811(5) 0.0686(9) Uani 1 1 d . . .
H10A H 0.3596 0.8634 0.9906 0.082 Uiso 1 1 calc R . .
C11 C 0.4826(5) 0.91280(18) 1.2281(6) 0.0898(13) Uani 1 1 d . . .
H11A H 0.5754 0.9051 1.2385 0.108 Uiso 1 1 calc R . .
C12 C 0.4768(6) 0.94933(19) 1.3611(6) 0.0968(16) Uani 1 1 d . . .
H12A H 0.5657 0.9657 1.4584 0.116 Uiso 1 1 calc R . .
C13 C 0.3439(6) 0.96202(15) 1.3531(5) 0.0851(13) Uani 1 1 d . . .
H13A H 0.3417 0.9870 1.4427 0.102 Uiso 1 1 calc R . .
C14 C 0.2113(4) 0.93684(12) 1.2083(4) 0.0614(9) Uani 1 1 d . . .
C15 C 0.0545(4) 0.94028(11) 1.1546(4) 0.0571(8) Uani 1 1 d . . .
C16 C -0.0259(4) 0.90554(11) 0.9899(4) 0.0520(8) Uani 1 1 d . . .
C17 C -0.1816(4) 0.89946(14) 0.8995(5) 0.0649(9) Uani 1 1 d . . .
H17A H -0.2346 0.8766 0.7892 0.078 Uiso 1 1 calc R . .
C18 C -0.2552(5) 0.92894(16) 0.9802(6) 0.0806(11) Uani 1 1 d . . .
H18A H -0.3595 0.9256 0.9226 0.097 Uiso 1 1 calc R . .
C19 C -0.1776(6) 0.96289(17) 1.1432(6) 0.0874(13) Uani 1 1 d . . .
H19A H -0.2301 0.9822 1.1933 0.105 Uiso 1 1 calc R . .
C20 C -0.0246(5) 0.96859(13) 1.2323(5) 0.0752(11) Uani 1 1 d . . .
H20A H 0.0270 0.9911 1.3441 0.090 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.391(4) . ?
N1 C9 1.392(4) . ?
N1 C6 1.430(3) . ?
O1 B1 1.343(5) . ?
O1 C1 1.444(4) . ?
O2 B1 1.357(4) . ?
O2 C2 1.442(4) . ?
B1 C3 1.542(4) . ?
C1 C2 1.508(6) . ?
C3 C8 1.385(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.382(4) . ?
C5 C6 1.372(4) . ?
C6 C7 1.374(4) . ?
C7 C8 1.382(4) . ?
C9 C10 1.387(5) . ?
C9 C14 1.412(4) . ?
C10 C11 1.371(5) . ?
C11 C12 1.380(6) . ?
C12 C13 1.363(6) . ?
C13 C14 1.396(5) . ?
C14 C15 1.442(5) . ?
C15 C16 1.399(4) . ?
C15 C20 1.403(5) . ?
C16 C17 1.389(4) . ?
C17 C18 1.390(5) . ?
C18 C19 1.376(6) . ?
C19 C20 1.363(6) . ?

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
C16 N1 C9 108.7(2) . . ?
C16 N1 C6 126.4(2) . . ?
C9 N1 C6 124.7(3) . . ?
B1 O1 C1 108.1(3) . . ?
B1 O2 C2 108.3(3) . . ?
O1 B1 O2 113.5(3) . . ?
O1 B1 C3 122.8(3) . . ?
O2 B1 C3 123.7(3) . . ?
O1 C1 C2 105.5(3) . . ?
O2 C2 C1 104.6(3) . . ?
C8 C3 C4 116.8(3) . . ?
C8 C3 B1 121.9(3) . . ?
C4 C3 B1 121.3(3) . . ?
C5 C4 C3 121.9(3) . . ?
C6 C5 C4 119.9(3) . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 N1 120.4(2) . . ?
C7 C6 N1 120.1(3) . . ?
C6 C7 C8 120.3(3) . . ?
C7 C8 C3 121.6(3) . . ?
C10 C9 N1 129.6(3) . . ?
C10 C9 C14 122.1(3) . . ?
N1 C9 C14 108.4(3) . . ?
C11 C10 C9 117.0(4) . . ?
C10 C11 C12 121.8(4) . . ?
C13 C12 C11 121.6(4) . . ?
C12 C13 C14 118.9(4) . . ?
C13 C14 C9 118.6(4) . . ?
C13 C14 C15 134.3(4) . . ?
C9 C14 C15 107.0(3) . . ?
C16 C15 C20 118.8(3) . . ?
C16 C15 C14 106.8(3) . . ?
C20 C15 C14 134.4(3) . . ?
C17 C16 N1 129.2(3) . . ?
C17 C16 C15 121.7(3) . . ?
N1 C16 C15 109.1(3) . . ?
C16 C17 C18 117.4(3) . . ?
C19 C18 C17 121.6(4) . . ?
C20 C19 C18 120.9(4) . . ?
C19 C20 C15 119.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1848443'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        DME
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 B N O2'
_chemical_formula_weight         355.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P21/c   '

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

_cell_length_a                   9.833(4)
_cell_length_b                   35.533(2)
_cell_length_c                   5.6192(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.816(6)
_cell_angle_gamma                90.00
_cell_volume                     1914.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1687
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      20.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11728
_diffrn_reflns_av_R_equivalents  0.1268
_diffrn_reflns_av_sigmaI/netI    0.1246
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4531
_reflns_number_gt                2133
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4531
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.1014
_refine_ls_wR_factor_ref         0.2032
_refine_ls_wR_factor_gt          0.1760
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7253(5) 0.01622(12) 0.1881(7) 0.0501(11) Uani 1 1 d . . .
O1 O 0.8072(4) 0.01489(6) 0.0246(5) 0.0637(9) Uani 1 1 d . . .
O2 O 0.6523(3) -0.01377(7) 0.2409(5) 0.0639(8) Uani 1 1 d . . .
C1 C 0.7946(5) 0.17116(10) 0.8739(7) 0.0571(11) Uani 1 1 d . . .
C2 C 0.9341(6) 0.16446(11) 0.9123(8) 0.0655(12) Uani 1 1 d . . .
H2A H 0.9691 0.1470 0.8178 0.079 Uiso 1 1 calc R . .
C3 C 1.0221(6) 0.18421(12) 1.0950(8) 0.0842(16) Uani 1 1 d . . .
H3A H 1.1176 0.1798 1.1255 0.101 Uiso 1 1 calc R . .
C4 C 0.9698(8) 0.21069(13) 1.2346(10) 0.0911(18) Uani 1 1 d . . .
H4A H 1.0307 0.2240 1.3558 0.109 Uiso 1 1 calc R . .
C5 C 0.8315(8) 0.21717(12) 1.1954(9) 0.0849(18) Uani 1 1 d . . .
H5A H 0.7980 0.2348 1.2902 0.102 Uiso 1 1 calc R . .
C6 C 0.7382(6) 0.19766(10) 1.0139(7) 0.0617(12) Uani 1 1 d . . .
C7 C 0.5906(7) 0.19656(10) 0.9337(8) 0.0717(15) Uani 1 1 d . . .
C8 C 0.4846(8) 0.21562(14) 1.0012(10) 0.0882(18) Uani 1 1 d . . .
H8A H 0.5043 0.2333 1.1258 0.106 Uiso 1 1 calc R . .
C9 C 0.3498(8) 0.20862(15) 0.8857(12) 0.101(2) Uani 1 1 d . . .
H9A H 0.2778 0.2217 0.9314 0.122 Uiso 1 1 calc R . .
C10 C 0.3188(7) 0.18175(15) 0.6979(11) 0.0941(17) Uani 1 1 d . . .
H10A H 0.2266 0.1770 0.6202 0.113 Uiso 1 1 calc R . .
C11 C 0.4256(7) 0.16243(13) 0.6293(9) 0.0827(15) Uani 1 1 d . . .
H11A H 0.4059 0.1448 0.5037 0.099 Uiso 1 1 calc R . .
C12 C 0.5606(6) 0.16929(11) 0.7469(8) 0.0625(11) Uani 1 1 d . . .
N1 N 0.6858(4) 0.15467(8) 0.7107(6) 0.0588(9) Uani 1 1 d . . .
C14 C 0.6962(5) 0.12070(9) 0.5766(6) 0.0525(10) Uani 1 1 d . . .
C15 C 0.6234(5) 0.08922(10) 0.6233(7) 0.0528(10) Uani 1 1 d . . .
H15A H 0.5683 0.0903 0.7378 0.063 Uiso 1 1 calc R . .
C16 C 0.6332(4) 0.05611(10) 0.4984(6) 0.0514(9) Uani 1 1 d . . .
H16A H 0.5851 0.0349 0.5318 0.062 Uiso 1 1 calc R . .
C17 C 0.7133(4) 0.05389(9) 0.3245(6) 0.0483(9) Uani 1 1 d . . .
C18 C 0.7821(5) 0.08623(10) 0.2793(6) 0.0541(10) Uani 1 1 d . . .
H18A H 0.8355 0.0855 0.1621 0.065 Uiso 1 1 calc R . .
C19 C 0.7738(5) 0.11941(10) 0.4023(7) 0.0598(12) Uani 1 1 d . . .
H19A H 0.8206 0.1407 0.3673 0.072 Uiso 1 1 calc R . .
C20 C 0.8157(5) -0.01919(9) -0.1079(7) 0.0640(13) Uani 1 1 d . . .
H20A H 0.9060 -0.0205 -0.1503 0.077 Uiso 1 1 calc R . .
H20B H 0.7447 -0.0188 -0.2585 0.077 Uiso 1 1 calc R . .
C21 C 0.7961(5) -0.05369(10) 0.0377(6) 0.0528(10) Uani 1 1 d . . .
C22 C 0.6620(5) -0.04919(10) 0.1204(8) 0.0641(12) Uani 1 1 d . . .
H22A H 0.5846 -0.0512 -0.0201 0.077 Uiso 1 1 calc R . .
H22B H 0.6537 -0.0695 0.2313 0.077 Uiso 1 1 calc R . .
C23 C 0.9178(5) -0.05817(12) 0.2552(7) 0.0701(13) Uani 1 1 d . . .
H23A H 0.9236 -0.0364 0.3584 0.105 Uiso 1 1 calc R . .
H23B H 1.0027 -0.0607 0.1992 0.105 Uiso 1 1 calc R . .
H23C H 0.9039 -0.0802 0.3457 0.105 Uiso 1 1 calc R . .
C24 C 0.7838(6) -0.08840(11) -0.1275(8) 0.0822(16) Uani 1 1 d . . .
H24A H 0.7062 -0.0853 -0.2637 0.123 Uiso 1 1 calc R . .
H24B H 0.7696 -0.1104 -0.0365 0.123 Uiso 1 1 calc R . .
H24C H 0.8679 -0.0913 -0.1857 0.123 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.350(5) . ?
B1 O2 1.354(5) . ?
B1 C17 1.560(5) . ?
O1 C20 1.434(4) . ?
O2 C22 1.442(4) . ?
C1 C2 1.361(6) . ?
C1 N1 1.376(6) . ?
C1 C6 1.417(5) . ?
C2 C3 1.379(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.395(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.348(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.422(7) . ?
C7 C8 1.365(7) . ?
C7 C12 1.411(6) . ?
C8 C9 1.363(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.406(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.380(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.367(7) . ?
C11 H11A 0.9300 . ?
C12 N1 1.392(5) . ?
N1 C14 1.439(4) . ?
C14 C19 1.369(5) . ?
C14 C15 1.384(5) . ?
C15 C16 1.384(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.387(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.385(5) . ?
C18 C19 1.378(5) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.510(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.501(6) . ?
C21 C23 1.517(6) . ?
C21 C24 1.532(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O2 123.1(3) . . ?
O1 B1 C17 119.1(3) . . ?
O2 B1 C17 117.8(3) . . ?
B1 O1 C20 119.7(3) . . ?
B1 O2 C22 119.4(3) . . ?
C2 C1 N1 129.7(4) . . ?
C2 C1 C6 122.2(4) . . ?
N1 C1 C6 108.1(4) . . ?
C1 C2 C3 118.2(5) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C2 C3 C4 120.9(6) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C5 C4 C3 120.5(6) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C1 117.4(5) . . ?
C5 C6 C7 134.8(5) . . ?
C1 C6 C7 107.7(4) . . ?
C8 C7 C12 120.1(6) . . ?
C8 C7 C6 133.4(5) . . ?
C12 C7 C6 106.6(4) . . ?
C9 C8 C7 119.9(5) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 120.5(6) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C11 C10 C9 119.7(6) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C12 C11 C10 119.6(5) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 N1 131.2(4) . . ?
C11 C12 C7 120.2(5) . . ?
N1 C12 C7 108.6(5) . . ?
C1 N1 C12 109.0(3) . . ?
C1 N1 C14 124.8(4) . . ?
C12 N1 C14 123.9(4) . . ?
C19 C14 C15 120.1(3) . . ?
C19 C14 N1 121.2(3) . . ?
C15 C14 N1 118.6(3) . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16A 119.3 . . ?
C17 C16 H16A 119.3 . . ?
C18 C17 C16 117.3(3) . . ?
C18 C17 B1 121.9(3) . . ?
C16 C17 B1 120.8(3) . . ?
C19 C18 C17 122.2(3) . . ?
C19 C18 H18A 118.9 . . ?
C17 C18 H18A 118.9 . . ?
C14 C19 C18 119.4(4) . . ?
C14 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
O1 C20 C21 112.0(3) . . ?
O1 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
O1 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 107.9(3) . . ?
C22 C21 C23 110.6(3) . . ?
C20 C21 C23 110.4(4) . . ?
C22 C21 C24 108.5(4) . . ?
C20 C21 C24 109.1(3) . . ?
C23 C21 C24 110.2(4) . . ?
O2 C22 C21 113.1(3) . . ?
O2 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
O2 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1848442'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        PE
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 B N O2'
_chemical_formula_weight         327.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   8.113(3)
_cell_length_b                   16.548(6)
_cell_length_c                   25.312(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.568(9)
_cell_angle_gamma                90.00
_cell_volume                     3397(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1774
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      19.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16997
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0952
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5977
_reflns_number_gt                3299
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.0700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0106(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5977
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0310(2) 0.91687(10) 1.12544(7) 0.0666(5) Uani 1 1 d . . .
O2 O 1.2418(2) 0.88129(11) 1.06761(7) 0.0728(6) Uani 1 1 d . . .
O3 O 0.7352(2) 0.85362(11) 0.56597(7) 0.0745(6) Uani 1 1 d . . .
O4 O 0.5091(2) 0.88864(10) 0.50988(7) 0.0715(6) Uani 1 1 d . . .
N1 N 0.5811(2) 0.77335(11) 0.93192(7) 0.0499(5) Uani 1 1 d . . .
N2 N 0.1162(3) 0.73623(11) 0.70615(7) 0.0494(5) Uani 1 1 d . . .
C1 C 0.4448(3) 0.81617(14) 0.91287(9) 0.0506(6) Uani 1 1 d . . .
C2 C 0.3961(4) 0.89392(15) 0.92300(11) 0.0672(8) Uani 1 1 d . . .
H2A H 0.4565 0.9266 0.9463 0.081 Uiso 1 1 calc R . .
C3 C 0.2569(4) 0.92188(18) 0.89801(13) 0.0818(9) Uani 1 1 d . . .
H3A H 0.2230 0.9746 0.9043 0.098 Uiso 1 1 calc R . .
C4 C 0.1648(4) 0.8744(2) 0.86365(13) 0.0879(11) Uani 1 1 d . . .
H4A H 0.0695 0.8951 0.8475 0.105 Uiso 1 1 calc R . .
C5 C 0.2126(4) 0.7975(2) 0.85320(10) 0.0730(9) Uani 1 1 d . . .
H5A H 0.1510 0.7656 0.8297 0.088 Uiso 1 1 calc R . .
C6 C 0.3544(3) 0.76702(15) 0.87787(9) 0.0542(7) Uani 1 1 d . . .
C7 C 0.4390(3) 0.69154(15) 0.87603(8) 0.0539(7) Uani 1 1 d . . .
C8 C 0.5780(3) 0.69728(14) 0.90966(8) 0.0494(6) Uani 1 1 d . . .
C9 C 0.6834(3) 0.63364(15) 0.91799(10) 0.0610(7) Uani 1 1 d . . .
H9A H 0.7741 0.6377 0.9411 0.073 Uiso 1 1 calc R . .
C10 C 0.6495(4) 0.56320(16) 0.89066(11) 0.0769(9) Uani 1 1 d . . .
H10A H 0.7187 0.5187 0.8951 0.092 Uiso 1 1 calc R . .
C11 C 0.5129(5) 0.55816(18) 0.85656(11) 0.0852(10) Uani 1 1 d . . .
H11A H 0.4940 0.5103 0.8381 0.102 Uiso 1 1 calc R . .
C12 C 0.4063(4) 0.62031(18) 0.84925(11) 0.0777(9) Uani 1 1 d . . .
H12A H 0.3140 0.6152 0.8269 0.093 Uiso 1 1 calc R . .
C13 C 0.7057(3) 0.80277(13) 0.96742(9) 0.0478(6) Uani 1 1 d . . .
C14 C 0.8669(3) 0.80210(15) 0.95396(10) 0.0595(7) Uani 1 1 d . . .
H14A H 0.8964 0.7832 0.9209 0.071 Uiso 1 1 calc R . .
C15 C 0.9867(3) 0.82961(15) 0.98943(10) 0.0606(7) Uani 1 1 d . . .
H15A H 1.0966 0.8284 0.9800 0.073 Uiso 1 1 calc R . .
C16 C 0.9472(3) 0.85885(13) 1.03856(9) 0.0484(6) Uani 1 1 d . . .
C17 C 0.7835(3) 0.85890(14) 1.05066(10) 0.0554(7) Uani 1 1 d . . .
H17A H 0.7532 0.8782 1.0835 0.066 Uiso 1 1 calc R . .
C18 C 0.6615(3) 0.83127(14) 1.01591(9) 0.0546(7) Uani 1 1 d . . .
H18A H 0.5515 0.8320 1.0253 0.065 Uiso 1 1 calc R . .
C19 C 1.1500(4) 0.94105(18) 1.16538(10) 0.0776(9) Uani 1 1 d . . .
H19A H 1.1741 0.8958 1.1887 0.093 Uiso 1 1 calc R . .
H19B H 1.1047 0.9843 1.1864 0.093 Uiso 1 1 calc R . .
C20 C 1.3022(4) 0.96852(18) 1.14158(12) 0.0774(9) Uani 1 1 d . . .
H20A H 1.2813 1.0184 1.1224 0.093 Uiso 1 1 calc R . .
H20B H 1.3845 0.9794 1.1692 0.093 Uiso 1 1 calc R . .
C21 C 1.3651(4) 0.90769(19) 1.10552(12) 0.0862(10) Uani 1 1 d . . .
H21A H 1.4578 0.9300 1.0870 0.103 Uiso 1 1 calc R . .
H21B H 1.4045 0.8615 1.1258 0.103 Uiso 1 1 calc R . .
C22 C -0.0176(3) 0.77413(14) 0.72803(9) 0.0470(6) Uani 1 1 d . . .
C23 C -0.0697(3) 0.85353(15) 0.72270(10) 0.0581(7) Uani 1 1 d . . .
H23A H -0.0149 0.8900 0.7014 0.070 Uiso 1 1 calc R . .
C24 C -0.2050(4) 0.87586(16) 0.75010(11) 0.0673(8) Uani 1 1 d . . .
H24A H -0.2422 0.9289 0.7470 0.081 Uiso 1 1 calc R . .
C25 C -0.2890(4) 0.82366(18) 0.78200(11) 0.0701(8) Uani 1 1 d . . .
H25A H -0.3813 0.8412 0.7997 0.084 Uiso 1 1 calc R . .
C26 C -0.2353(3) 0.74545(17) 0.78745(10) 0.0618(7) Uani 1 1 d . . .
H26A H -0.2903 0.7097 0.8092 0.074 Uiso 1 1 calc R . .
C27 C -0.0991(3) 0.72020(15) 0.76050(9) 0.0475(6) Uani 1 1 d . . .
C28 C -0.0090(3) 0.64556(14) 0.75847(9) 0.0463(6) Uani 1 1 d . . .
C29 C 0.1205(3) 0.65646(13) 0.72465(9) 0.0447(6) Uani 1 1 d . . .
C30 C 0.2265(3) 0.59465(14) 0.71219(9) 0.0539(7) Uani 1 1 d . . .
H30A H 0.3105 0.6022 0.6884 0.065 Uiso 1 1 calc R . .
C31 C 0.2032(4) 0.52165(15) 0.73632(10) 0.0608(8) Uani 1 1 d . . .
H31A H 0.2728 0.4788 0.7287 0.073 Uiso 1 1 calc R . .
C32 C 0.0793(4) 0.51032(15) 0.77153(11) 0.0643(8) Uani 1 1 d . . .
H32A H 0.0693 0.4605 0.7881 0.077 Uiso 1 1 calc R . .
C33 C -0.0297(3) 0.57057(15) 0.78279(9) 0.0586(7) Uani 1 1 d . . .
H33A H -0.1149 0.5619 0.8059 0.070 Uiso 1 1 calc R . .
C34 C 0.2296(3) 0.77089(13) 0.67102(9) 0.0481(6) Uani 1 1 d . . .
C35 C 0.3961(3) 0.76666(14) 0.68154(9) 0.0533(7) Uani 1 1 d . . .
H35A H 0.4354 0.7431 0.7128 0.064 Uiso 1 1 calc R . .
C36 C 0.5049(3) 0.79722(13) 0.64601(9) 0.0540(7) Uani 1 1 d . . .
H36A H 0.6175 0.7928 0.6534 0.065 Uiso 1 1 calc R . .
C37 C 0.4519(3) 0.83450(13) 0.59937(9) 0.0506(7) Uani 1 1 d . . .
C38 C 0.2824(3) 0.84032(15) 0.59126(10) 0.0590(7) Uani 1 1 d . . .
H38A H 0.2421 0.8664 0.5610 0.071 Uiso 1 1 calc R . .
C39 C 0.1720(3) 0.80949(14) 0.62574(9) 0.0569(7) Uani 1 1 d . . .
H39A H 0.0593 0.8144 0.6188 0.068 Uiso 1 1 calc R . .
C40 C 0.8485(4) 0.8730(2) 0.52574(12) 0.0911(10) Uani 1 1 d . . .
H40A H 0.8775 0.8241 0.5071 0.109 Uiso 1 1 calc R . .
H40B H 0.9486 0.8949 0.5420 0.109 Uiso 1 1 calc R . .
C41 C 0.7792(4) 0.93253(18) 0.48740(11) 0.0793(9) Uani 1 1 d . . .
H41A H 0.7704 0.9848 0.5044 0.095 Uiso 1 1 calc R . .
H41B H 0.8528 0.9381 0.4581 0.095 Uiso 1 1 calc R . .
C42 C 0.6168(4) 0.90715(18) 0.46759(11) 0.0771(9) Uani 1 1 d . . .
H42A H 0.5685 0.9499 0.4460 0.093 Uiso 1 1 calc R . .
H42B H 0.6284 0.8598 0.4454 0.093 Uiso 1 1 calc R . .
B1 B 1.0826(4) 0.88756(16) 1.07914(12) 0.0516(8) Uani 1 1 d . . .
B2 B 0.5727(4) 0.86031(16) 0.55661(12) 0.0531(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
O1 B1 1.346(3) . ?
O1 C19 1.436(3) . ?
O2 B1 1.337(4) . ?
O2 C21 1.435(3) . ?
O3 B2 1.338(3) . ?
O3 C40 1.427(3) . ?
O4 B2 1.361(3) . ?
O4 C42 1.434(3) . ?
N1 C8 1.379(3) . ?
N1 C1 1.389(3) . ?
N1 C13 1.420(3) . ?
N2 C22 1.383(3) . ?
N2 C29 1.401(3) . ?
N2 C34 1.418(3) . ?
C1 C2 1.372(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.360(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.358(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.427(3) . ?
C7 C12 1.382(3) . ?
C7 C8 1.397(3) . ?
C8 C9 1.370(3) . ?
C9 C10 1.379(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.388(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.353(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.360(3) . ?
C13 C18 1.372(3) . ?
C14 C15 1.382(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.380(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.371(3) . ?
C16 B1 1.557(4) . ?
C17 C18 1.384(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.461(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.460(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.386(3) . ?
C22 C27 1.392(3) . ?
C23 C24 1.366(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.376(4) . ?
C24 H24A 0.9300 . ?
C25 C26 1.371(3) . ?
C25 H25A 0.9300 . ?
C26 C27 1.380(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.437(3) . ?
C28 C29 1.385(3) . ?
C28 C33 1.397(3) . ?
C29 C30 1.379(3) . ?
C30 C31 1.369(3) . ?
C30 H30A 0.9300 . ?
C31 C32 1.375(4) . ?
C31 H31A 0.9300 . ?
C32 C33 1.368(4) . ?
C32 H32A 0.9300 . ?
C33 H33A 0.9300 . ?
C34 C35 1.371(3) . ?
C34 C39 1.382(3) . ?
C35 C36 1.374(3) . ?
C35 H35A 0.9300 . ?
C36 C37 1.390(3) . ?
C36 H36A 0.9300 . ?
C37 C38 1.388(3) . ?
C37 B2 1.540(4) . ?
C38 C39 1.366(3) . ?
C38 H38A 0.9300 . ?
C39 H39A 0.9300 . ?
C40 C41 1.483(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C42 1.459(4) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C19 119.6(2) . . ?
B1 O2 C21 119.4(2) . . ?
B2 O3 C40 120.4(2) . . ?
B2 O4 C42 119.9(2) . . ?
C8 N1 C1 108.58(18) . . ?
C8 N1 C13 125.2(2) . . ?
C1 N1 C13 126.25(19) . . ?
C22 N2 C29 107.8(2) . . ?
C22 N2 C34 126.7(2) . . ?
C29 N2 C34 125.5(2) . . ?
C2 C1 N1 130.1(2) . . ?
C2 C1 C6 121.1(2) . . ?
N1 C1 C6 108.8(2) . . ?
C3 C2 C1 118.1(2) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C5 C6 C1 119.2(2) . . ?
C5 C6 C7 134.2(2) . . ?
C1 C6 C7 106.6(2) . . ?
C12 C7 C8 119.9(3) . . ?
C12 C7 C6 132.6(2) . . ?
C8 C7 C6 107.6(2) . . ?
C9 C8 N1 129.4(2) . . ?
C9 C8 C7 122.1(2) . . ?
N1 C8 C7 108.4(2) . . ?
C8 C9 C10 117.2(3) . . ?
C8 C9 H9A 121.4 . . ?
C10 C9 H9A 121.4 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C12 C11 C10 122.4(3) . . ?
C12 C11 H11A 118.8 . . ?
C10 C11 H11A 118.8 . . ?
C11 C12 C7 117.9(3) . . ?
C11 C12 H12A 121.1 . . ?
C7 C12 H12A 121.1 . . ?
C14 C13 C18 120.2(2) . . ?
C14 C13 N1 120.8(2) . . ?
C18 C13 N1 119.0(2) . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C16 C15 C14 121.6(3) . . ?
C16 C15 H15A 119.2 . . ?
C14 C15 H15A 119.2 . . ?
C17 C16 C15 116.9(2) . . ?
C17 C16 B1 121.5(2) . . ?
C15 C16 B1 121.6(2) . . ?
C16 C17 C18 122.5(2) . . ?
C16 C17 H17A 118.7 . . ?
C18 C17 H17A 118.7 . . ?
C13 C18 C17 118.9(2) . . ?
C13 C18 H18A 120.6 . . ?
C17 C18 H18A 120.6 . . ?
O1 C19 C20 110.9(2) . . ?
O1 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 110.9(3) . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.0 . . ?
O2 C21 C20 112.3(2) . . ?
O2 C21 H21A 109.2 . . ?
C20 C21 H21A 109.2 . . ?
O2 C21 H21B 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
N2 C22 C23 129.2(2) . . ?
N2 C22 C27 109.7(2) . . ?
C23 C22 C27 121.1(3) . . ?
C24 C23 C22 117.0(3) . . ?
C24 C23 H23A 121.5 . . ?
C22 C23 H23A 121.5 . . ?
C23 C24 C25 123.1(3) . . ?
C23 C24 H24A 118.4 . . ?
C25 C24 H24A 118.4 . . ?
C26 C25 C24 119.4(3) . . ?
C26 C25 H25A 120.3 . . ?
C24 C25 H25A 120.3 . . ?
C25 C26 C27 119.5(3) . . ?
C25 C26 H26A 120.2 . . ?
C27 C26 H26A 120.2 . . ?
C26 C27 C22 119.8(2) . . ?
C26 C27 C28 133.9(2) . . ?
C22 C27 C28 106.2(2) . . ?
C29 C28 C33 119.4(2) . . ?
C29 C28 C27 107.8(2) . . ?
C33 C28 C27 132.8(3) . . ?
C30 C29 C28 122.2(2) . . ?
C30 C29 N2 129.2(3) . . ?
C28 C29 N2 108.5(2) . . ?
C31 C30 C29 117.2(3) . . ?
C31 C30 H30A 121.4 . . ?
C29 C30 H30A 121.4 . . ?
C30 C31 C32 121.5(3) . . ?
C30 C31 H31A 119.3 . . ?
C32 C31 H31A 119.3 . . ?
C33 C32 C31 121.6(3) . . ?
C33 C32 H32A 119.2 . . ?
C31 C32 H32A 119.2 . . ?
C32 C33 C28 118.0(3) . . ?
C32 C33 H33A 121.0 . . ?
C28 C33 H33A 121.0 . . ?
C35 C34 C39 119.6(2) . . ?
C35 C34 N2 120.7(2) . . ?
C39 C34 N2 119.8(2) . . ?
C34 C35 C36 120.1(2) . . ?
C34 C35 H35A 120.0 . . ?
C36 C35 H35A 120.0 . . ?
C35 C36 C37 122.0(2) . . ?
C35 C36 H36A 119.0 . . ?
C37 C36 H36A 119.0 . . ?
C38 C37 C36 116.0(2) . . ?
C38 C37 B2 121.6(2) . . ?
C36 C37 B2 122.1(2) . . ?
C39 C38 C37 122.9(2) . . ?
C39 C38 H38A 118.5 . . ?
C37 C38 H38A 118.5 . . ?
C38 C39 C34 119.3(2) . . ?
C38 C39 H39A 120.3 . . ?
C34 C39 H39A 120.3 . . ?
O3 C40 C41 112.1(2) . . ?
O3 C40 H40A 109.2 . . ?
C41 C40 H40A 109.2 . . ?
O3 C40 H40B 109.2 . . ?
C41 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
C42 C41 C40 110.9(3) . . ?
C42 C41 H41A 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 108.0 . . ?
O4 C42 C41 111.6(2) . . ?
O4 C42 H42A 109.3 . . ?
C41 C42 H42A 109.3 . . ?
O4 C42 H42B 109.3 . . ?
C41 C42 H42B 109.3 . . ?
H42A C42 H42B 108.0 . . ?
O2 B1 O1 122.9(2) . . ?
O2 B1 C16 120.1(3) . . ?
O1 B1 C16 117.0(3) . . ?
O3 B2 O4 122.1(3) . . ?
O3 B2 C37 119.7(2) . . ?
O4 B2 C37 118.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1848440'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        IPE
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 B N O2'
_chemical_formula_weight         326.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0038(19)
_cell_length_b                   17.3205(12)
_cell_length_c                   26.7265(10)
_cell_angle_alpha                101.028(11)
_cell_angle_beta                 91.667(10)
_cell_angle_gamma                100.889(2)
_cell_volume                     3563.0(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1134
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      16.77

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9802
_exptl_absorpt_correction_T_max  0.9863
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18143
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.1428
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             12452
_reflns_number_gt                3928
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12452
_refine_ls_number_parameters     902
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.2327
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7534(5) 0.9418(3) 0.17036(15) 0.1297(16) Uani 1 1 d . . .
O2 O 0.9460(5) 0.8929(2) 0.11878(14) 0.0987(12) Uani 1 1 d . . .
O3 O 0.8498(6) 0.6597(3) 0.07696(15) 0.1238(15) Uani 1 1 d . . .
O4 O 0.6192(5) 0.6300(3) 0.02140(17) 0.1231(15) Uani 1 1 d . . .
O5 O -0.0895(5) 0.4198(3) 0.37512(17) 0.1261(15) Uani 1 1 d D . .
O6 O -0.3059(6) 0.3844(3) 0.42540(17) 0.1332(16) Uani 1 1 d . . .
O7 O -0.1911(5) 0.1384(3) 0.44275(16) 0.1216(15) Uani 1 1 d . . .
O8 O -0.4006(5) 0.1749(2) 0.39735(14) 0.1129(14) Uani 1 1 d . . .
C1 C 0.0130(9) 0.7786(5) -0.0933(2) 0.0900(19) Uani 1 1 d . . .
C2 C -0.1177(10) 0.8046(6) -0.1169(3) 0.124(3) Uani 1 1 d . . .
H2A H -0.1950 0.7691 -0.1413 0.149 Uiso 1 1 calc R . .
C3 C -0.1293(11) 0.8831(7) -0.1036(3) 0.138(3) Uani 1 1 d . . .
H3A H -0.2168 0.9014 -0.1185 0.166 Uiso 1 1 calc R . .
C4 C -0.0113(10) 0.9365(4) -0.0677(3) 0.117(2) Uani 1 1 d . . .
H4A H -0.0193 0.9903 -0.0599 0.140 Uiso 1 1 calc R . .
C5 C 0.1205(8) 0.9108(5) -0.0429(2) 0.0969(19) Uani 1 1 d . . .
H5A H 0.1986 0.9461 -0.0187 0.116 Uiso 1 1 calc R . .
C6 C 0.1272(8) 0.8309(5) -0.0564(2) 0.0826(17) Uani 1 1 d . . .
N1 N 0.2444(6) 0.7897(3) -0.03886(16) 0.0816(13) Uani 1 1 d . . .
C8 C 0.2050(9) 0.7107(5) -0.0650(2) 0.0839(18) Uani 1 1 d . . .
C9 C 0.0608(8) 0.7033(5) -0.0988(2) 0.0864(19) Uani 1 1 d . . .
C10 C 0.0027(10) 0.6293(6) -0.1297(3) 0.123(3) Uani 1 1 d . . .
H10A H -0.0900 0.6224 -0.1530 0.148 Uiso 1 1 calc R . .
C11 C 0.0776(13) 0.5660(6) -0.1269(3) 0.141(4) Uani 1 1 d . . .
H11A H 0.0362 0.5164 -0.1481 0.169 Uiso 1 1 calc R . .
C12 C 0.2206(11) 0.5756(5) -0.0912(3) 0.124(3) Uani 1 1 d . . .
H12A H 0.2702 0.5319 -0.0890 0.149 Uiso 1 1 calc R . .
C13 C 0.2862(8) 0.6497(5) -0.0597(2) 0.100(2) Uani 1 1 d . . .
H13A H 0.3794 0.6573 -0.0364 0.120 Uiso 1 1 calc R . .
C14 C 0.3800(8) 0.8230(3) 0.0010(2) 0.0760(15) Uani 1 1 d . . .
C15 C 0.3426(7) 0.8586(3) 0.0486(2) 0.0797(16) Uani 1 1 d . . .
H15A H 0.2312 0.8634 0.0553 0.096 Uiso 1 1 calc R . .
C16 C 0.4727(7) 0.8873(3) 0.08649(19) 0.0834(16) Uani 1 1 d . . .
H16A H 0.4469 0.9121 0.1186 0.100 Uiso 1 1 calc R . .
C17 C 0.6417(7) 0.8806(3) 0.0785(2) 0.0735(15) Uani 1 1 d . . .
C18 C 0.6747(7) 0.8454(3) 0.0297(2) 0.0823(16) Uani 1 1 d . . .
H18A H 0.7855 0.8399 0.0228 0.099 Uiso 1 1 calc R . .
C19 C 0.5451(8) 0.8181(3) -0.0092(2) 0.0861(17) Uani 1 1 d . . .
H19A H 0.5705 0.7965 -0.0420 0.103 Uiso 1 1 calc R . .
C20 C 1.0335(8) 0.9224(4) 0.1689(2) 0.126(2) Uani 1 1 d . . .
H20A H 1.1323 0.9639 0.1675 0.151 Uiso 1 1 calc R . .
H20B H 1.0713 0.8791 0.1814 0.151 Uiso 1 1 calc R . .
C21 C 0.9098(10) 0.9551(8) 0.2025(3) 0.243(6) Uani 1 1 d . . .
C22 C 0.9339(9) 1.0057(5) 0.2418(3) 0.185(4) Uani 1 1 d . . .
H22A H 0.8263 1.0160 0.2534 0.278 Uiso 1 1 calc R . .
H22B H 1.0023 1.0543 0.2356 0.278 Uiso 1 1 calc R . .
H22C H 0.9919 0.9866 0.2675 0.278 Uiso 1 1 calc R . .
C23 C 0.1058(7) 0.7280(4) 0.2419(2) 0.0705(15) Uani 1 1 d . . .
C24 C 0.0217(8) 0.6509(4) 0.2227(2) 0.0833(16) Uani 1 1 d . . .
H24A H 0.0617 0.6189 0.1955 0.100 Uiso 1 1 calc R . .
C25 C -0.1259(8) 0.6220(4) 0.2453(2) 0.0986(19) Uani 1 1 d . . .
H25A H -0.1848 0.5697 0.2331 0.118 Uiso 1 1 calc R . .
C26 C -0.1864(8) 0.6699(5) 0.2856(3) 0.098(2) Uani 1 1 d . . .
H26A H -0.2858 0.6497 0.2999 0.118 Uiso 1 1 calc R . .
C27 C -0.1008(9) 0.7465(4) 0.3045(2) 0.0938(19) Uani 1 1 d . . .
H27A H -0.1407 0.7786 0.3317 0.113 Uiso 1 1 calc R . .
C28 C 0.0467(8) 0.7758(4) 0.2824(2) 0.0766(16) Uani 1 1 d . . .
C29 C 0.1666(8) 0.8499(4) 0.2944(2) 0.0714(15) Uani 1 1 d . . .
C30 C 0.2938(7) 0.8448(4) 0.2592(2) 0.0677(14) Uani 1 1 d . . .
N2 N 0.2569(6) 0.7701(3) 0.22758(15) 0.0717(12) Uani 1 1 d . . .
C32 C 0.4292(7) 0.9083(4) 0.2598(2) 0.0805(16) Uani 1 1 d . . .
H32A H 0.5120 0.9039 0.2363 0.097 Uiso 1 1 calc R . .
C33 C 0.4388(8) 0.9773(4) 0.2953(3) 0.0935(18) Uani 1 1 d . . .
H33A H 0.5291 1.0202 0.2961 0.112 Uiso 1 1 calc R . .
C34 C 0.3138(10) 0.9836(4) 0.3304(2) 0.106(2) Uani 1 1 d . . .
H34A H 0.3212 1.0311 0.3543 0.128 Uiso 1 1 calc R . .
C35 C 0.1809(9) 0.9212(4) 0.3301(2) 0.0929(19) Uani 1 1 d . . .
H35A H 0.0992 0.9264 0.3539 0.111 Uiso 1 1 calc R . .
C36 C 0.3596(7) 0.7403(3) 0.1886(2) 0.0706(14) Uani 1 1 d . . .
C37 C 0.5303(7) 0.7420(3) 0.2006(2) 0.0837(16) Uani 1 1 d . . .
H37A H 0.5769 0.7616 0.2339 0.100 Uiso 1 1 calc R . .
C38 C 0.6315(7) 0.7142(3) 0.1622(2) 0.0854(17) Uani 1 1 d . . .
H38A H 0.7460 0.7156 0.1703 0.102 Uiso 1 1 calc R . .
C39 C 0.5656(7) 0.6850(3) 0.1128(2) 0.0733(15) Uani 1 1 d . . .
C40 C 0.3920(8) 0.6824(3) 0.10249(19) 0.0847(16) Uani 1 1 d . . .
H40A H 0.3440 0.6607 0.0695 0.102 Uiso 1 1 calc R . .
C41 C 0.2884(7) 0.7110(3) 0.1398(2) 0.0833(17) Uani 1 1 d . . .
H41A H 0.1742 0.7103 0.1318 0.100 Uiso 1 1 calc R . .
C42 C 0.9135(10) 0.6330(5) 0.0276(3) 0.162(3) Uani 1 1 d . . .
H42A H 0.9543 0.5836 0.0268 0.194 Uiso 1 1 calc R . .
H42B H 1.0063 0.6735 0.0205 0.194 Uiso 1 1 calc R . .
C43 C 0.7644(11) 0.6201(5) -0.0107(3) 0.157(3) Uani 1 1 d . . .
C44 C 0.7211(10) 0.5392(5) -0.0399(3) 0.207(4) Uani 1 1 d . . .
H44A H 0.6240 0.5342 -0.0631 0.310 Uiso 1 1 calc R . .
H44B H 0.6944 0.5026 -0.0172 0.310 Uiso 1 1 calc R . .
H44C H 0.8160 0.5270 -0.0589 0.310 Uiso 1 1 calc R . .
C45 C 0.2778(8) 0.2112(4) 0.56207(19) 0.0721(15) Uani 1 1 d . . .
C46 C 0.4023(8) 0.2048(4) 0.5984(2) 0.0749(16) Uani 1 1 d . . .
C47 C 0.3862(9) 0.1350(5) 0.6171(2) 0.096(2) Uani 1 1 d . . .
H47A H 0.4682 0.1296 0.6409 0.115 Uiso 1 1 calc R . .
C48 C 0.2486(10) 0.0732(4) 0.6005(3) 0.105(2) Uani 1 1 d . . .
H48A H 0.2350 0.0270 0.6141 0.126 Uiso 1 1 calc R . .
C49 C 0.1286(8) 0.0806(4) 0.5629(2) 0.0978(19) Uani 1 1 d . . .
H49A H 0.0390 0.0376 0.5510 0.117 Uiso 1 1 calc R . .
C50 C 0.1392(8) 0.1497(4) 0.5431(2) 0.0883(17) Uani 1 1 d . . .
H50A H 0.0588 0.1545 0.5186 0.106 Uiso 1 1 calc R . .
N4 N 0.3217(6) 0.2853(3) 0.54844(16) 0.0775(12) Uani 1 1 d . . .
C52 C 0.4781(8) 0.3264(4) 0.5757(2) 0.0755(15) Uani 1 1 d . . .
C53 C 0.5268(8) 0.2772(4) 0.6070(2) 0.0790(16) Uani 1 1 d . . .
C54 C 0.6802(9) 0.3035(5) 0.6386(2) 0.100(2) Uani 1 1 d . . .
H54 H 0.7158 0.2716 0.6594 0.120 Uiso 1 1 calc R . .
C55 C 0.7727(10) 0.3771(6) 0.6371(3) 0.123(3) Uani 1 1 d . . .
H55A H 0.8739 0.3957 0.6575 0.147 Uiso 1 1 calc R . .
C56 C 0.7215(9) 0.4257(4) 0.6062(3) 0.116(2) Uani 1 1 d . . .
H56A H 0.7890 0.4757 0.6061 0.140 Uiso 1 1 calc R . .
C57 C 0.5690(8) 0.4001(4) 0.5752(2) 0.0938(18) Uani 1 1 d . . .
H57 H 0.5320 0.4328 0.5552 0.113 Uiso 1 1 calc R . .
C58 C 0.2168(7) 0.3177(3) 0.5173(2) 0.0760(15) Uani 1 1 d . . .
C59 C 0.2740(7) 0.3433(3) 0.4742(2) 0.0880(17) Uani 1 1 d . . .
H59A H 0.3855 0.3428 0.4656 0.106 Uiso 1 1 calc R . .
C60 C 0.1619(8) 0.3699(3) 0.4437(2) 0.0904(17) Uani 1 1 d . . .
H60A H 0.2009 0.3871 0.4145 0.108 Uiso 1 1 calc R . .
C61 C -0.0055(8) 0.3720(3) 0.4552(2) 0.0841(17) Uani 1 1 d . . .
C62 C -0.0573(7) 0.3475(3) 0.4992(2) 0.0960(18) Uani 1 1 d . . .
H62A H -0.1684 0.3483 0.5082 0.115 Uiso 1 1 calc R . .
C63 C 0.0525(8) 0.3217(3) 0.5305(2) 0.0919(18) Uani 1 1 d . . .
H63A H 0.0153 0.3069 0.5606 0.110 Uiso 1 1 calc R . .
C64 C -0.2499(11) 0.4270(7) 0.3515(4) 0.223(5) Uani 1 1 d D . .
C65 C -0.3915(9) 0.4005(5) 0.3803(3) 0.164(3) Uani 1 1 d D . .
H65A H -0.4658 0.3523 0.3612 0.197 Uiso 1 1 calc R . .
H65B H -0.4575 0.4420 0.3898 0.197 Uiso 1 1 calc R . .
C66 C -0.2439(10) 0.4735(6) 0.3211(4) 0.278(7) Uani 1 1 d D . .
H66A H -0.1308 0.4841 0.3096 0.417 Uiso 1 1 calc R . .
H66B H -0.2729 0.5229 0.3379 0.417 Uiso 1 1 calc R . .
H66C H -0.3235 0.4492 0.2923 0.417 Uiso 1 1 calc R . .
C67 C 0.3871(6) 0.2197(4) 0.23704(18) 0.0704(15) Uani 1 1 d . . .
C68 C 0.3999(6) 0.1405(4) 0.23568(18) 0.0801(16) Uani 1 1 d . . .
H68A H 0.3329 0.1088 0.2549 0.096 Uiso 1 1 calc R . .
C69 C 0.5181(7) 0.1112(4) 0.2041(2) 0.0913(18) Uani 1 1 d . . .
H69A H 0.5300 0.0582 0.2018 0.110 Uiso 1 1 calc R . .
C70 C 0.6198(7) 0.1595(5) 0.1757(2) 0.102(2) Uani 1 1 d . . .
H70A H 0.6990 0.1384 0.1553 0.123 Uiso 1 1 calc R . .
C71 C 0.6040(7) 0.2373(5) 0.1777(2) 0.095(2) Uani 1 1 d . . .
H71A H 0.6723 0.2692 0.1589 0.114 Uiso 1 1 calc R . .
C72 C 0.4830(7) 0.2683(4) 0.20852(19) 0.0763(16) Uani 1 1 d . . .
C73 C 0.4319(7) 0.3428(4) 0.2168(2) 0.0755(16) Uani 1 1 d . . .
C74 C 0.3030(7) 0.3377(4) 0.25125(19) 0.0733(15) Uani 1 1 d . . .
N3 N 0.2750(5) 0.2623(3) 0.26383(14) 0.0725(12) Uani 1 1 d . . .
C76 C 0.2263(7) 0.4016(4) 0.2695(2) 0.0893(18) Uani 1 1 d . . .
H76A H 0.1434 0.3976 0.2931 0.107 Uiso 1 1 calc R . .
C77 C 0.2766(9) 0.4715(4) 0.2518(2) 0.112(2) Uani 1 1 d . . .
H77A H 0.2276 0.5156 0.2634 0.134 Uiso 1 1 calc R . .
C78 C 0.4018(10) 0.4761(4) 0.2161(3) 0.109(2) Uani 1 1 d . . .
H78A H 0.4320 0.5229 0.2035 0.131 Uiso 1 1 calc R . .
C79 C 0.4791(8) 0.4138(5) 0.1997(2) 0.097(2) Uani 1 1 d . . .
H79A H 0.5643 0.4187 0.1769 0.117 Uiso 1 1 calc R . .
C80 C 0.1460(7) 0.2329(3) 0.29605(18) 0.0692(14) Uani 1 1 d . . .
C81 C 0.1935(6) 0.2025(3) 0.33734(19) 0.0776(16) Uani 1 1 d . . .
H81A H 0.3064 0.1991 0.3438 0.093 Uiso 1 1 calc R . .
C82 C 0.0682(7) 0.1770(3) 0.36900(18) 0.0803(16) Uani 1 1 d . . .
H82A H 0.0990 0.1554 0.3964 0.096 Uiso 1 1 calc R . .
C83 C -0.1028(7) 0.1828(3) 0.3610(2) 0.0719(15) Uani 1 1 d . . .
C84 C -0.1442(6) 0.2119(3) 0.3181(2) 0.0824(16) Uani 1 1 d . . .
H84A H -0.2570 0.2150 0.3113 0.099 Uiso 1 1 calc R . .
C85 C -0.0234(7) 0.2363(3) 0.28523(19) 0.0825(16) Uani 1 1 d . . .
H85A H -0.0549 0.2547 0.2565 0.099 Uiso 1 1 calc R . .
C86 C -0.4740(8) 0.1592(5) 0.4449(2) 0.162(3) Uani 1 1 d . . .
H86A H -0.5115 0.2061 0.4634 0.194 Uiso 1 1 calc R . .
H86B H -0.5703 0.1145 0.4379 0.194 Uiso 1 1 calc R . .
C87 C -0.3394(15) 0.1407(6) 0.4734(4) 0.180(4) Uani 1 1 d U . .
C88 C -0.3478(9) 0.0980(5) 0.5068(4) 0.240(5) Uani 1 1 d . . .
H88A H -0.2384 0.0850 0.5126 0.360 Uiso 1 1 calc R . .
H88B H -0.4308 0.0495 0.4952 0.360 Uiso 1 1 calc R . .
H88C H -0.3807 0.1270 0.5381 0.360 Uiso 1 1 calc R . .
B1 B 0.7813(9) 0.9058(4) 0.1227(3) 0.086(2) Uani 1 1 d . . .
B2 B 0.6787(11) 0.6566(5) 0.0699(3) 0.095(2) Uani 1 1 d . . .
B3 B -0.1325(11) 0.3948(5) 0.4190(3) 0.096(2) Uani 1 1 d . . .
B4 B -0.2347(9) 0.1641(4) 0.4001(3) 0.082(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
O1 B1 1.353(7) . ?
O1 C21 1.453(7) . ?
O2 B1 1.381(7) . ?
O2 C20 1.446(5) . ?
O3 B2 1.367(8) . ?
O3 C42 1.452(6) . ?
O4 B2 1.331(7) . ?
O4 C43 1.481(7) . ?
O5 B3 1.358(7) . ?
O5 C64 1.451(7) . ?
O6 B3 1.385(8) . ?
O6 C65 1.467(6) . ?
O7 B4 1.359(7) . ?
O7 C87 1.464(10) . ?
O8 B4 1.377(7) . ?
O8 C86 1.466(5) . ?
C1 C6 1.387(7) . ?
C1 C2 1.394(8) . ?
C1 C9 1.408(8) . ?
C2 C3 1.360(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.394(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.414(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.372(7) . ?
C5 H5A 0.9300 . ?
C6 N1 1.402(7) . ?
N1 C8 1.384(7) . ?
N1 C14 1.452(6) . ?
C8 C13 1.367(7) . ?
C8 C9 1.416(7) . ?
C9 C10 1.375(8) . ?
C10 C11 1.358(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.432(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.393(8) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.371(6) . ?
C14 C19 1.372(6) . ?
C15 C16 1.380(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.398(6) . ?
C16 H16A 0.9300 . ?
C17 C18 1.386(6) . ?
C17 B1 1.540(8) . ?
C18 C19 1.394(6) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.476(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.218(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.371(6) . ?
C23 C28 1.385(6) . ?
C23 N2 1.393(6) . ?
C24 C25 1.394(6) . ?
C24 H24A 0.9300 . ?
C25 C26 1.387(7) . ?
C25 H25A 0.9300 . ?
C26 C27 1.366(7) . ?
C26 H26A 0.9300 . ?
C27 C28 1.387(7) . ?
C27 H27A 0.9300 . ?
C28 C29 1.425(7) . ?
C29 C35 1.392(7) . ?
C29 C30 1.410(6) . ?
C30 N2 1.377(6) . ?
C30 C32 1.388(6) . ?
N2 C36 1.426(5) . ?
C32 C33 1.364(6) . ?
C32 H32A 0.9300 . ?
C33 C34 1.397(7) . ?
C33 H33A 0.9300 . ?
C34 C35 1.364(7) . ?
C34 H34A 0.9300 . ?
C35 H35A 0.9300 . ?
C36 C41 1.371(6) . ?
C36 C37 1.388(6) . ?
C37 C38 1.396(6) . ?
C37 H37A 0.9300 . ?
C38 C39 1.371(6) . ?
C38 H38A 0.9300 . ?
C39 C40 1.399(6) . ?
C39 B2 1.545(8) . ?
C40 C41 1.393(6) . ?
C40 H40A 0.9300 . ?
C41 H41A 0.9300 . ?
C42 C43 1.505(9) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C44 1.439(9) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 N4 1.385(6) . ?
C45 C50 1.393(7) . ?
C45 C46 1.406(6) . ?
C46 C47 1.380(7) . ?
C46 C53 1.422(7) . ?
C47 C48 1.378(7) . ?
C47 H47A 0.9300 . ?
C48 C49 1.410(7) . ?
C48 H48A 0.9300 . ?
C49 C50 1.388(6) . ?
C49 H49A 0.9300 . ?
C50 H50A 0.9300 . ?
N4 C52 1.420(6) . ?
N4 C58 1.424(6) . ?
C52 C57 1.348(7) . ?
C52 C53 1.398(6) . ?
C53 C54 1.417(7) . ?
C54 C55 1.356(8) . ?
C54 H54 0.9300 . ?
C55 C56 1.392(8) . ?
C55 H55A 0.9300 . ?
C56 C57 1.403(7) . ?
C56 H56A 0.9300 . ?
C57 H57 0.9300 . ?
C58 C59 1.372(6) . ?
C58 C63 1.382(6) . ?
C59 C60 1.393(6) . ?
C59 H59A 0.9300 . ?
C60 C61 1.389(6) . ?
C60 H60A 0.9300 . ?
C61 C62 1.373(6) . ?
C61 B3 1.539(8) . ?
C62 C63 1.386(6) . ?
C62 H62A 0.9300 . ?
C63 H63A 0.9300 . ?
C64 C66 1.245(8) . ?
C64 C65 1.441(8) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
C67 C72 1.384(6) . ?
C67 C68 1.387(6) . ?
C67 N3 1.396(6) . ?
C68 C69 1.389(6) . ?
C68 H68A 0.9300 . ?
C69 C70 1.400(6) . ?
C69 H69A 0.9300 . ?
C70 C71 1.368(7) . ?
C70 H70A 0.9300 . ?
C71 C72 1.407(7) . ?
C71 H71A 0.9300 . ?
C72 C73 1.406(7) . ?
C73 C79 1.382(7) . ?
C73 C74 1.405(6) . ?
C74 C76 1.381(6) . ?
C74 N3 1.389(6) . ?
N3 C80 1.445(5) . ?
C76 C77 1.378(7) . ?
C76 H76A 0.9300 . ?
C77 C78 1.405(7) . ?
C77 H77A 0.9300 . ?
C78 C79 1.352(7) . ?
C78 H78A 0.9300 . ?
C79 H79A 0.9300 . ?
C80 C81 1.383(6) . ?
C80 C85 1.393(6) . ?
C81 C82 1.393(5) . ?
C81 H81A 0.9300 . ?
C82 C83 1.404(6) . ?
C82 H82A 0.9300 . ?
C83 C84 1.393(6) . ?
C83 B4 1.541(7) . ?
C84 C85 1.388(6) . ?
C84 H84A 0.9300 . ?
C85 H85A 0.9300 . ?
C86 C87 1.420(10) . ?
C86 H86A 0.9700 . ?
C86 H86B 0.9700 . ?
C87 C88 1.259(9) . ?
C88 H88A 0.9600 . ?
C88 H88B 0.9600 . ?
C88 H88C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C21 108.4(5) . . ?
B1 O2 C20 107.2(5) . . ?
B2 O3 C42 108.2(5) . . ?
B2 O4 C43 108.9(6) . . ?
B3 O5 C64 104.4(6) . . ?
B3 O6 C65 108.6(5) . . ?
B4 O7 C87 104.3(6) . . ?
B4 O8 C86 106.9(5) . . ?
C6 C1 C2 121.0(8) . . ?
C6 C1 C9 106.5(7) . . ?
C2 C1 C9 132.5(8) . . ?
C3 C2 C1 118.5(9) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 120.6(9) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 C5 121.6(8) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C6 C5 C4 116.6(7) . . ?
C6 C5 H5A 121.7 . . ?
C4 C5 H5A 121.7 . . ?
C5 C6 C1 121.7(7) . . ?
C5 C6 N1 128.8(7) . . ?
C1 C6 N1 109.4(7) . . ?
C8 N1 C6 108.2(6) . . ?
C8 N1 C14 125.8(6) . . ?
C6 N1 C14 126.1(6) . . ?
C13 C8 N1 127.6(7) . . ?
C13 C8 C9 125.2(7) . . ?
N1 C8 C9 107.2(7) . . ?
C10 C9 C1 134.6(8) . . ?
C10 C9 C8 116.7(8) . . ?
C1 C9 C8 108.7(7) . . ?
C11 C10 C9 121.5(9) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C10 C11 C12 120.0(9) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C13 C12 C11 120.8(8) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C8 C13 C12 115.8(7) . . ?
C8 C13 H13A 122.1 . . ?
C12 C13 H13A 122.1 . . ?
C15 C14 C19 120.4(5) . . ?
C15 C14 N1 120.1(5) . . ?
C19 C14 N1 119.6(5) . . ?
C14 C15 C16 119.0(5) . . ?
C14 C15 H15A 120.5 . . ?
C16 C15 H15A 120.5 . . ?
C15 C16 C17 122.6(5) . . ?
C15 C16 H16A 118.7 . . ?
C17 C16 H16A 118.7 . . ?
C18 C17 C16 116.6(5) . . ?
C18 C17 B1 121.7(6) . . ?
C16 C17 B1 121.6(5) . . ?
C17 C18 C19 121.3(5) . . ?
C17 C18 H18A 119.4 . . ?
C19 C18 H18A 119.4 . . ?
C14 C19 C18 120.0(5) . . ?
C14 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
O2 C20 C21 106.5(5) . . ?
O2 C20 H20A 110.4 . . ?
C21 C20 H20A 110.4 . . ?
O2 C20 H20B 110.4 . . ?
C21 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C22 C21 O1 120.5(8) . . ?
C22 C21 C20 130.0(8) . . ?
O1 C21 C20 105.4(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 121.2(6) . . ?
C24 C23 N2 129.3(6) . . ?
C28 C23 N2 109.4(6) . . ?
C23 C24 C25 117.7(6) . . ?
C23 C24 H24A 121.1 . . ?
C25 C24 H24A 121.1 . . ?
C26 C25 C24 121.2(6) . . ?
C26 C25 H25A 119.4 . . ?
C24 C25 H25A 119.4 . . ?
C27 C26 C25 120.4(6) . . ?
C27 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
C26 C27 C28 118.9(6) . . ?
C26 C27 H27A 120.5 . . ?
C28 C27 H27A 120.5 . . ?
C23 C28 C27 120.5(6) . . ?
C23 C28 C29 107.0(6) . . ?
C27 C28 C29 132.5(6) . . ?
C35 C29 C30 117.7(6) . . ?
C35 C29 C28 135.4(6) . . ?
C30 C29 C28 106.9(6) . . ?
N2 C30 C32 129.7(6) . . ?
N2 C30 C29 108.7(5) . . ?
C32 C30 C29 121.6(6) . . ?
C30 N2 C23 107.9(5) . . ?
C30 N2 C36 125.8(5) . . ?
C23 N2 C36 126.2(5) . . ?
C33 C32 C30 119.0(6) . . ?
C33 C32 H32A 120.5 . . ?
C30 C32 H32A 120.5 . . ?
C32 C33 C34 120.3(6) . . ?
C32 C33 H33A 119.9 . . ?
C34 C33 H33A 119.9 . . ?
C35 C34 C33 120.9(6) . . ?
C35 C34 H34A 119.6 . . ?
C33 C34 H34A 119.6 . . ?
C34 C35 C29 120.6(6) . . ?
C34 C35 H35A 119.7 . . ?
C29 C35 H35A 119.7 . . ?
C41 C36 C37 121.1(5) . . ?
C41 C36 N2 119.4(5) . . ?
C37 C36 N2 119.5(5) . . ?
C36 C37 C38 119.4(5) . . ?
C36 C37 H37A 120.3 . . ?
C38 C37 H37A 120.3 . . ?
C39 C38 C37 121.3(5) . . ?
C39 C38 H38A 119.3 . . ?
C37 C38 H38A 119.3 . . ?
C38 C39 C40 117.5(5) . . ?
C38 C39 B2 121.4(6) . . ?
C40 C39 B2 121.1(6) . . ?
C41 C40 C39 122.5(5) . . ?
C41 C40 H40A 118.8 . . ?
C39 C40 H40A 118.8 . . ?
C36 C41 C40 118.1(5) . . ?
C36 C41 H41A 120.9 . . ?
C40 C41 H41A 120.9 . . ?
O3 C42 C43 105.6(6) . . ?
O3 C42 H42A 110.6 . . ?
C43 C42 H42A 110.6 . . ?
O3 C42 H42B 110.6 . . ?
C43 C42 H42B 110.6 . . ?
H42A C42 H42B 108.8 . . ?
C44 C43 O4 105.4(7) . . ?
C44 C43 C42 113.2(8) . . ?
O4 C43 C42 103.6(6) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N4 C45 C50 128.0(6) . . ?
N4 C45 C46 108.8(6) . . ?
C50 C45 C46 123.2(6) . . ?
C47 C46 C45 119.0(7) . . ?
C47 C46 C53 133.6(7) . . ?
C45 C46 C53 107.4(6) . . ?
C48 C47 C46 120.0(7) . . ?
C48 C47 H47A 120.0 . . ?
C46 C47 H47A 120.0 . . ?
C47 C48 C49 119.6(7) . . ?
C47 C48 H48A 120.2 . . ?
C49 C48 H48A 120.2 . . ?
C50 C49 C48 122.5(6) . . ?
C50 C49 H49A 118.7 . . ?
C48 C49 H49A 118.7 . . ?
C49 C50 C45 115.7(6) . . ?
C49 C50 H50A 122.1 . . ?
C45 C50 H50A 122.1 . . ?
C45 N4 C52 108.1(5) . . ?
C45 N4 C58 125.2(5) . . ?
C52 N4 C58 126.2(5) . . ?
C57 C52 C53 122.6(7) . . ?
C57 C52 N4 129.5(6) . . ?
C53 C52 N4 107.8(6) . . ?
C52 C53 C54 119.9(7) . . ?
C52 C53 C46 107.8(6) . . ?
C54 C53 C46 132.3(7) . . ?
C55 C54 C53 117.2(7) . . ?
C55 C54 H54 121.4 . . ?
C53 C54 H54 121.4 . . ?
C54 C55 C56 122.3(8) . . ?
C54 C55 H55A 118.9 . . ?
C56 C55 H55A 118.9 . . ?
C55 C56 C57 120.6(7) . . ?
C55 C56 H56A 119.7 . . ?
C57 C56 H56A 119.7 . . ?
C52 C57 C56 117.4(6) . . ?
C52 C57 H57 121.3 . . ?
C56 C57 H57 121.3 . . ?
C59 C58 C63 119.6(5) . . ?
C59 C58 N4 121.5(5) . . ?
C63 C58 N4 118.9(5) . . ?
C58 C59 C60 118.8(5) . . ?
C58 C59 H59A 120.6 . . ?
C60 C59 H59A 120.6 . . ?
C61 C60 C59 122.7(5) . . ?
C61 C60 H60A 118.7 . . ?
C59 C60 H60A 118.7 . . ?
C62 C61 C60 116.9(5) . . ?
C62 C61 B3 120.7(6) . . ?
C60 C61 B3 122.2(6) . . ?
C61 C62 C63 121.4(5) . . ?
C61 C62 H62A 119.3 . . ?
C63 C62 H62A 119.3 . . ?
C58 C63 C62 120.5(5) . . ?
C58 C63 H63A 119.7 . . ?
C62 C63 H63A 119.7 . . ?
C66 C64 C65 127.4(9) . . ?
C66 C64 O5 117.5(8) . . ?
C65 C64 O5 111.4(6) . . ?
C64 C65 O6 102.3(6) . . ?
C64 C65 H65A 111.3 . . ?
O6 C65 H65A 111.3 . . ?
C64 C65 H65B 111.3 . . ?
O6 C65 H65B 111.3 . . ?
H65A C65 H65B 109.2 . . ?
C64 C66 H66A 109.5 . . ?
C64 C66 H66B 109.5 . . ?
H66A C66 H66B 109.5 . . ?
C64 C66 H66C 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C72 C67 C68 123.4(6) . . ?
C72 C67 N3 108.7(6) . . ?
C68 C67 N3 127.8(5) . . ?
C67 C68 C69 116.4(5) . . ?
C67 C68 H68A 121.8 . . ?
C69 C68 H68A 121.8 . . ?
C68 C69 C70 121.5(6) . . ?
C68 C69 H69A 119.3 . . ?
C70 C69 H69A 119.3 . . ?
C71 C70 C69 120.8(6) . . ?
C71 C70 H70A 119.6 . . ?
C69 C70 H70A 119.6 . . ?
C70 C71 C72 119.1(6) . . ?
C70 C71 H71A 120.5 . . ?
C72 C71 H71A 120.5 . . ?
C67 C72 C73 108.7(6) . . ?
C67 C72 C71 118.7(6) . . ?
C73 C72 C71 132.6(6) . . ?
C79 C73 C74 118.3(6) . . ?
C79 C73 C72 135.6(6) . . ?
C74 C73 C72 106.1(6) . . ?
C76 C74 N3 128.2(6) . . ?
C76 C74 C73 122.2(6) . . ?
N3 C74 C73 109.5(6) . . ?
C74 N3 C67 107.0(5) . . ?
C74 N3 C80 125.8(5) . . ?
C67 N3 C80 127.1(5) . . ?
C77 C76 C74 117.9(6) . . ?
C77 C76 H76A 121.1 . . ?
C74 C76 H76A 121.1 . . ?
C76 C77 C78 120.1(7) . . ?
C76 C77 H77A 120.0 . . ?
C78 C77 H77A 120.0 . . ?
C79 C78 C77 121.2(7) . . ?
C79 C78 H78A 119.4 . . ?
C77 C78 H78A 119.4 . . ?
C78 C79 C73 120.2(6) . . ?
C78 C79 H79A 119.9 . . ?
C73 C79 H79A 119.9 . . ?
C81 C80 C85 121.3(5) . . ?
C81 C80 N3 119.3(5) . . ?
C85 C80 N3 119.4(5) . . ?
C80 C81 C82 118.5(5) . . ?
C80 C81 H81A 120.8 . . ?
C82 C81 H81A 120.8 . . ?
C81 C82 C83 122.3(5) . . ?
C81 C82 H82A 118.8 . . ?
C83 C82 H82A 118.8 . . ?
C84 C83 C82 116.7(5) . . ?
C84 C83 B4 121.7(5) . . ?
C82 C83 B4 121.4(5) . . ?
C85 C84 C83 122.5(5) . . ?
C85 C84 H84A 118.8 . . ?
C83 C84 H84A 118.8 . . ?
C84 C85 C80 118.6(5) . . ?
C84 C85 H85A 120.7 . . ?
C80 C85 H85A 120.7 . . ?
C87 C86 O8 104.8(7) . . ?
C87 C86 H86A 110.8 . . ?
O8 C86 H86A 110.8 . . ?
C87 C86 H86B 110.8 . . ?
O8 C86 H86B 110.8 . . ?
H86A C86 H86B 108.9 . . ?
C88 C87 C86 129.0(11) . . ?
C88 C87 O7 114.3(10) . . ?
C86 C87 O7 109.8(8) . . ?
C87 C88 H88A 109.5 . . ?
C87 C88 H88B 109.5 . . ?
H88A C88 H88B 109.5 . . ?
C87 C88 H88C 109.5 . . ?
H88A C88 H88C 109.5 . . ?
H88B C88 H88C 109.5 . . ?
O1 B1 O2 112.4(6) . . ?
O1 B1 C17 122.9(6) . . ?
O2 B1 C17 124.6(6) . . ?
O4 B2 O3 113.1(6) . . ?
O4 B2 C39 122.7(7) . . ?
O3 B2 C39 124.2(7) . . ?
O5 B3 O6 113.0(6) . . ?
O5 B3 C61 123.6(7) . . ?
O6 B3 C61 123.1(7) . . ?
O7 B4 O8 113.9(5) . . ?
O7 B4 C83 121.1(6) . . ?
O8 B4 C83 124.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_a_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1848441'
_audit_update_record             
;
2018-06-11 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        TME
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 B N O2'
_chemical_formula_weight         369.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2/c   '

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

_cell_length_a                   24.979(2)
_cell_length_b                   8.9400(10)
_cell_length_c                   19.1000(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.664(12)
_cell_angle_gamma                90.00
_cell_volume                     4126.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1797
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      20.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20104
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_sigmaI/netI    0.1471
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7257
_reflns_number_gt                3607
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7257
_refine_ls_number_parameters     505
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1477
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1607
_refine_ls_goodness_of_fit_ref   1.016
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.07690(9) 0.4724(3) 0.09706(14) 0.0770(7) Uani 1 1 d . . .
O2 O -0.01294(9) 0.2920(3) 0.11505(14) 0.0772(7) Uani 1 1 d . . .
O3 O 0.48467(9) -0.1546(3) 0.12711(15) 0.0832(8) Uani 1 1 d . . .
O4 O 0.54469(10) 0.0277(3) 0.12721(15) 0.0822(8) Uani 1 1 d . . .
C1 C 0.15637(13) 0.9876(4) 0.2257(2) 0.0590(9) Uani 1 1 d . . .
C2 C 0.13650(14) 1.0399(4) 0.1563(2) 0.0753(11) Uani 1 1 d . . .
H2A H 0.1083 0.9902 0.1234 0.090 Uiso 1 1 calc R . .
C3 C 0.15956(16) 1.1670(5) 0.1371(2) 0.0857(12) Uani 1 1 d . . .
H3A H 0.1467 1.2046 0.0905 0.103 Uiso 1 1 calc R . .
C4 C 0.20147(17) 1.2405(5) 0.1855(3) 0.0916(13) Uani 1 1 d . . .
H4A H 0.2164 1.3271 0.1712 0.110 Uiso 1 1 calc R . .
C5 C 0.22128(15) 1.1879(5) 0.2541(3) 0.0800(12) Uani 1 1 d . . .
H5A H 0.2495 1.2385 0.2865 0.096 Uiso 1 1 calc R . .
C6 C 0.19922(12) 1.0594(4) 0.2752(2) 0.0609(9) Uani 1 1 d . . .
C7 C 0.20982(12) 0.9756(4) 0.3405(2) 0.0611(10) Uani 1 1 d . . .
C8 C 0.17278(13) 0.8561(4) 0.3295(2) 0.0588(9) Uani 1 1 d . . .
N1 N 0.14082(10) 0.8632(3) 0.25891(17) 0.0607(8) Uani 1 1 d . . .
C10 C 0.16953(14) 0.7572(4) 0.3830(2) 0.0697(10) Uani 1 1 d . . .
H10A H 0.1438 0.6799 0.3749 0.084 Uiso 1 1 calc R . .
C11 C 0.20650(17) 0.7781(5) 0.4495(2) 0.0811(11) Uani 1 1 d . . .
H11A H 0.2056 0.7129 0.4872 0.097 Uiso 1 1 calc R . .
C12 C 0.24453(17) 0.8921(6) 0.4617(3) 0.0890(13) Uani 1 1 d . . .
H12A H 0.2693 0.9015 0.5069 0.107 Uiso 1 1 calc R . .
C13 C 0.24639(14) 0.9911(5) 0.4086(3) 0.0783(12) Uani 1 1 d . . .
H13A H 0.2719 1.0689 0.4175 0.094 Uiso 1 1 calc R . .
C14 C 0.10038(13) 0.7571(4) 0.22499(19) 0.0593(9) Uani 1 1 d . . .
C15 C 0.11344(13) 0.6089(4) 0.2242(2) 0.0670(10) Uani 1 1 d . . .
H15A H 0.1492 0.5766 0.2458 0.080 Uiso 1 1 calc R . .
C16 C 0.07375(13) 0.5081(4) 0.1917(2) 0.0679(10) Uani 1 1 d . . .
H16A H 0.0829 0.4072 0.1920 0.081 Uiso 1 1 calc R . .
C17 C 0.02050(13) 0.5520(4) 0.15825(19) 0.0598(9) Uani 1 1 d . . .
C18 C 0.00896(13) 0.7019(4) 0.1598(2) 0.0680(10) Uani 1 1 d . . .
H18A H -0.0266 0.7349 0.1378 0.082 Uiso 1 1 calc R . .
C19 C 0.04787(13) 0.8043(4) 0.1923(2) 0.0670(10) Uani 1 1 d . . .
H19A H 0.0388 0.9052 0.1923 0.080 Uiso 1 1 calc R . .
C20 C -0.10488(14) 0.3423(4) 0.0605(2) 0.0685(10) Uani 1 1 d . . .
C21 C -0.1130(2) 0.3685(6) -0.0201(3) 0.1298(18) Uani 1 1 d . . .
H21A H -0.1389 0.4485 -0.0356 0.195 Uiso 1 1 calc R . .
H21B H -0.1269 0.2789 -0.0461 0.195 Uiso 1 1 calc R . .
H21C H -0.0782 0.3946 -0.0295 0.195 Uiso 1 1 calc R . .
C22 C -0.15946(15) 0.3298(5) 0.0787(3) 0.1120(17) Uani 1 1 d . . .
H22A H -0.1828 0.4114 0.0570 0.168 Uiso 1 1 calc R . .
H22B H -0.1539 0.3330 0.1302 0.168 Uiso 1 1 calc R . .
H22C H -0.1767 0.2368 0.0604 0.168 Uiso 1 1 calc R . .
C23 C -0.06430(14) 0.2153(4) 0.0903(2) 0.0758(11) Uani 1 1 d . . .
C24 C -0.07453(19) 0.1457(6) 0.1585(3) 0.131(2) Uani 1 1 d . . .
H24A H -0.0478 0.0682 0.1756 0.197 Uiso 1 1 calc R . .
H24B H -0.1111 0.1039 0.1478 0.197 Uiso 1 1 calc R . .
H24C H -0.0711 0.2211 0.1951 0.197 Uiso 1 1 calc R . .
C25 C -0.0596(2) 0.0928(6) 0.0403(3) 0.146(2) Uani 1 1 d . . .
H25A H -0.0546 0.1342 -0.0040 0.219 Uiso 1 1 calc R . .
H25B H -0.0927 0.0336 0.0301 0.219 Uiso 1 1 calc R . .
H25C H -0.0284 0.0310 0.0622 0.219 Uiso 1 1 calc R . .
C26 C 0.32074(12) 0.5392(4) 0.17043(18) 0.0517(8) Uani 1 1 d . . .
C27 C 0.32130(14) 0.5890(4) 0.10283(19) 0.0722(10) Uani 1 1 d . . .
H27A H 0.3411 0.5388 0.0748 0.087 Uiso 1 1 calc R . .
C28 C 0.29168(16) 0.7154(5) 0.0781(2) 0.0806(12) Uani 1 1 d . . .
H28A H 0.2914 0.7517 0.0324 0.097 Uiso 1 1 calc R . .
C29 C 0.26248(14) 0.7896(4) 0.1189(2) 0.0734(11) Uani 1 1 d . . .
H29A H 0.2428 0.8753 0.1005 0.088 Uiso 1 1 calc R . .
C30 C 0.26177(12) 0.7404(4) 0.1858(2) 0.0616(9) Uani 1 1 d . . .
H30A H 0.2417 0.7916 0.2131 0.074 Uiso 1 1 calc R . .
C31 C 0.29144(11) 0.6127(4) 0.21317(17) 0.0490(8) Uani 1 1 d . . .
N2 N 0.34781(10) 0.4179(3) 0.20901(14) 0.0524(7) Uani 1 1 d . . .
C33 C 0.33767(11) 0.4170(3) 0.27618(17) 0.0458(8) Uani 1 1 d . . .
C34 C 0.30210(11) 0.5347(3) 0.28053(17) 0.0466(8) Uani 1 1 d . . .
C35 C 0.28698(13) 0.5587(4) 0.3439(2) 0.0614(9) Uani 1 1 d . . .
H35A H 0.2629 0.6359 0.3475 0.074 Uiso 1 1 calc R . .
C36 C 0.30800(14) 0.4670(4) 0.4016(2) 0.0683(10) Uani 1 1 d . . .
H36A H 0.2975 0.4812 0.4444 0.082 Uiso 1 1 calc R . .
C37 C 0.34457(14) 0.3539(4) 0.3973(2) 0.0645(9) Uani 1 1 d . . .
H37A H 0.3591 0.2949 0.4378 0.077 Uiso 1 1 calc R . .
C38 C 0.35978(12) 0.3271(4) 0.33476(19) 0.0551(8) Uani 1 1 d . . .
H38A H 0.3843 0.2505 0.3318 0.066 Uiso 1 1 calc R . .
C39 C 0.38248(12) 0.3137(4) 0.18498(16) 0.0513(8) Uani 1 1 d . . .
C40 C 0.43168(13) 0.3595(4) 0.1739(2) 0.0683(10) Uani 1 1 d . . .
H40A H 0.4415 0.4600 0.1787 0.082 Uiso 1 1 calc R . .
C41 C 0.46672(13) 0.2566(4) 0.15568(19) 0.0672(10) Uani 1 1 d . . .
H41A H 0.5002 0.2886 0.1480 0.081 Uiso 1 1 calc R . .
C42 C 0.45331(13) 0.1074(4) 0.14853(17) 0.0545(8) Uani 1 1 d . . .
C43 C 0.40286(14) 0.0661(4) 0.15763(19) 0.0674(10) Uani 1 1 d . . .
H43A H 0.3923 -0.0337 0.1515 0.081 Uiso 1 1 calc R . .
C44 C 0.36722(14) 0.1685(4) 0.1756(2) 0.0659(10) Uani 1 1 d . . .
H44A H 0.3330 0.1378 0.1813 0.079 Uiso 1 1 calc R . .
C45 C 0.57378(14) -0.1045(4) 0.11550(19) 0.0628(9) Uani 1 1 d . . .
C46 C 0.62722(18) -0.1057(5) 0.1706(3) 0.1118(16) Uani 1 1 d . . .
H46A H 0.6493 -0.0228 0.1625 0.168 Uiso 1 1 calc R . .
H46B H 0.6463 -0.1975 0.1672 0.168 Uiso 1 1 calc R . .
H46C H 0.6207 -0.0975 0.2179 0.168 Uiso 1 1 calc R . .
C47 C 0.5859(2) -0.0893(6) 0.0434(3) 0.1150(16) Uani 1 1 d . . .
H47A H 0.6119 -0.0093 0.0450 0.173 Uiso 1 1 calc R . .
H47B H 0.5523 -0.0677 0.0075 0.173 Uiso 1 1 calc R . .
H47C H 0.6015 -0.1810 0.0313 0.173 Uiso 1 1 calc R . .
C48 C 0.53298(15) -0.2297(4) 0.1186(2) 0.0747(11) Uani 1 1 d U . .
C49 C 0.5158(3) -0.3219(8) 0.0535(4) 0.211(3) Uani 1 1 d U . .
H49A H 0.5047 -0.2585 0.0118 0.317 Uiso 1 1 calc R . .
H49B H 0.4853 -0.3841 0.0571 0.317 Uiso 1 1 calc R . .
H49C H 0.5462 -0.3837 0.0490 0.317 Uiso 1 1 calc R . .
C50 C 0.5512(2) -0.3246(7) 0.1852(4) 0.186(3) Uani 1 1 d U . .
H50A H 0.5239 -0.4005 0.1850 0.279 Uiso 1 1 calc R . .
H50B H 0.5552 -0.2630 0.2274 0.279 Uiso 1 1 calc R . .
H50C H 0.5860 -0.3708 0.1860 0.279 Uiso 1 1 calc R . .
B1 B -0.02384(16) 0.4381(5) 0.1230(2) 0.0587(10) Uani 1 1 d . . .
B2 B 0.49440(16) -0.0073(5) 0.1333(2) 0.0556(10) 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
O1 B1 1.328(4) . ?
O1 C20 1.442(4) . ?
O2 B1 1.350(5) . ?
O2 C23 1.426(4) . ?
O3 B2 1.338(4) . ?
O3 C48 1.426(4) . ?
O4 B2 1.328(4) . ?
O4 C45 1.434(4) . ?
C1 C2 1.375(5) . ?
C1 N1 1.384(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.365(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.362(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.378(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.422(5) . ?
C7 C13 1.394(5) . ?
C7 C8 1.394(4) . ?
C8 C10 1.369(5) . ?
C8 N1 1.384(4) . ?
N1 C14 1.417(4) . ?
C10 C11 1.381(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.356(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.366(4) . ?
C14 C19 1.369(4) . ?
C15 C16 1.367(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.373(4) . ?
C17 B1 1.529(5) . ?
C18 C19 1.365(4) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C22 1.494(5) . ?
C20 C21 1.519(6) . ?
C20 C23 1.533(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C25 1.477(6) . ?
C23 C24 1.523(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.369(4) . ?
C26 N2 1.387(4) . ?
C26 C31 1.391(4) . ?
C27 C28 1.367(5) . ?
C27 H27A 0.9300 . ?
C28 C29 1.367(5) . ?
C28 H28A 0.9300 . ?
C29 C30 1.356(5) . ?
C29 H29A 0.9300 . ?
C30 C31 1.389(4) . ?
C30 H30A 0.9300 . ?
C31 C34 1.428(4) . ?
N2 C33 1.369(4) . ?
N2 C39 1.425(4) . ?
C33 C38 1.375(4) . ?
C33 C34 1.393(4) . ?
C34 C35 1.373(4) . ?
C35 C36 1.366(5) . ?
C35 H35A 0.9300 . ?
C36 C37 1.379(5) . ?
C36 H36A 0.9300 . ?
C37 C38 1.363(4) . ?
C37 H37A 0.9300 . ?
C38 H38A 0.9300 . ?
C39 C44 1.352(4) . ?
C39 C40 1.362(4) . ?
C40 C41 1.374(4) . ?
C40 H40A 0.9300 . ?
C41 C42 1.373(4) . ?
C41 H41A 0.9300 . ?
C42 C43 1.366(4) . ?
C42 B2 1.531(5) . ?
C43 C44 1.379(4) . ?
C43 H43A 0.9300 . ?
C44 H44A 0.9300 . ?
C45 C46 1.476(5) . ?
C45 C47 1.489(5) . ?
C45 C48 1.525(5) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C49 1.462(6) . ?
C48 C50 1.501(6) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 C20 108.1(3) . . ?
B1 O2 C23 108.2(3) . . ?
B2 O3 C48 109.5(3) . . ?
B2 O4 C45 110.3(3) . . ?
C2 C1 N1 129.8(3) . . ?
C2 C1 C6 121.7(4) . . ?
N1 C1 C6 108.4(4) . . ?
C3 C2 C1 117.9(4) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C2 C3 C4 121.3(4) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 C7 134.2(4) . . ?
C1 C6 C7 107.0(3) . . ?
C13 C7 C8 118.0(4) . . ?
C13 C7 C6 134.4(4) . . ?
C8 C7 C6 107.6(3) . . ?
C10 C8 N1 128.9(3) . . ?
C10 C8 C7 123.0(4) . . ?
N1 C8 C7 108.0(3) . . ?
C8 N1 C1 108.9(3) . . ?
C8 N1 C14 125.7(3) . . ?
C1 N1 C14 125.3(3) . . ?
C8 C10 C11 116.5(4) . . ?
C8 C10 H10A 121.7 . . ?
C11 C10 H10A 121.7 . . ?
C12 C11 C10 122.0(4) . . ?
C12 C11 H11A 119.0 . . ?
C10 C11 H11A 119.0 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C7 119.7(4) . . ?
C12 C13 H13A 120.2 . . ?
C7 C13 H13A 120.2 . . ?
C15 C14 C19 119.9(3) . . ?
C15 C14 N1 120.6(3) . . ?
C19 C14 N1 119.5(3) . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
C15 C16 C17 121.8(3) . . ?
C15 C16 H16A 119.1 . . ?
C17 C16 H16A 119.1 . . ?
C18 C17 C16 116.8(3) . . ?
C18 C17 B1 121.8(3) . . ?
C16 C17 B1 121.4(3) . . ?
C19 C18 C17 122.4(3) . . ?
C19 C18 H18A 118.8 . . ?
C17 C18 H18A 118.8 . . ?
C18 C19 C14 119.4(3) . . ?
C18 C19 H19A 120.3 . . ?
C14 C19 H19A 120.3 . . ?
O1 C20 C22 107.9(3) . . ?
O1 C20 C21 106.9(3) . . ?
C22 C20 C21 110.6(3) . . ?
O1 C20 C23 102.9(3) . . ?
C22 C20 C23 114.5(3) . . ?
C21 C20 C23 113.3(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 C25 111.0(3) . . ?
O2 C23 C24 104.1(3) . . ?
C25 C23 C24 108.0(4) . . ?
O2 C23 C20 102.8(3) . . ?
C25 C23 C20 117.6(4) . . ?
C24 C23 C20 112.4(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 N2 129.4(3) . . ?
C27 C26 C31 122.2(3) . . ?
N2 C26 C31 108.4(3) . . ?
C28 C27 C26 117.4(3) . . ?
C28 C27 H27A 121.3 . . ?
C26 C27 H27A 121.3 . . ?
C29 C28 C27 121.6(4) . . ?
C29 C28 H28A 119.2 . . ?
C27 C28 H28A 119.2 . . ?
C30 C29 C28 121.1(4) . . ?
C30 C29 H29A 119.4 . . ?
C28 C29 H29A 119.4 . . ?
C29 C30 C31 119.2(3) . . ?
C29 C30 H30A 120.4 . . ?
C31 C30 H30A 120.4 . . ?
C30 C31 C26 118.5(3) . . ?
C30 C31 C34 134.4(3) . . ?
C26 C31 C34 107.0(3) . . ?
C33 N2 C26 108.7(2) . . ?
C33 N2 C39 124.7(3) . . ?
C26 N2 C39 126.5(3) . . ?
N2 C33 C38 129.4(3) . . ?
N2 C33 C34 108.9(3) . . ?
C38 C33 C34 121.6(3) . . ?
C35 C34 C33 119.5(3) . . ?
C35 C34 C31 133.4(3) . . ?
C33 C34 C31 106.9(3) . . ?
C36 C35 C34 118.8(3) . . ?
C36 C35 H35A 120.6 . . ?
C34 C35 H35A 120.6 . . ?
C35 C36 C37 121.2(3) . . ?
C35 C36 H36A 119.4 . . ?
C37 C36 H36A 119.4 . . ?
C38 C37 C36 121.1(3) . . ?
C38 C37 H37A 119.5 . . ?
C36 C37 H37A 119.5 . . ?
C37 C38 C33 117.8(3) . . ?
C37 C38 H38A 121.1 . . ?
C33 C38 H38A 121.1 . . ?
C44 C39 C40 120.2(3) . . ?
C44 C39 N2 119.8(3) . . ?
C40 C39 N2 119.9(3) . . ?
C39 C40 C41 119.7(3) . . ?
C39 C40 H40A 120.1 . . ?
C41 C40 H40A 120.1 . . ?
C42 C41 C40 121.3(3) . . ?
C42 C41 H41A 119.3 . . ?
C40 C41 H41A 119.3 . . ?
C43 C42 C41 117.4(3) . . ?
C43 C42 B2 121.9(3) . . ?
C41 C42 B2 120.8(3) . . ?
C42 C43 C44 121.8(3) . . ?
C42 C43 H43A 119.1 . . ?
C44 C43 H43A 119.1 . . ?
C39 C44 C43 119.4(3) . . ?
C39 C44 H44A 120.3 . . ?
C43 C44 H44A 120.3 . . ?
O4 C45 C46 107.3(3) . . ?
O4 C45 C47 107.4(3) . . ?
C46 C45 C47 107.5(4) . . ?
O4 C45 C48 103.2(2) . . ?
C46 C45 C48 117.4(3) . . ?
C47 C45 C48 113.4(3) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O3 C48 C49 106.8(4) . . ?
O3 C48 C50 104.6(3) . . ?
C49 C48 C50 111.3(5) . . ?
O3 C48 C45 104.6(3) . . ?
C49 C48 C45 115.9(4) . . ?
C50 C48 C45 112.7(4) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
O1 B1 O2 113.1(3) . . ?
O1 B1 C17 123.6(4) . . ?
O2 B1 C17 123.3(3) . . ?
O4 B2 O3 112.3(3) . . ?
O4 B2 C42 123.6(3) . . ?
O3 B2 C42 124.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.046
