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

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

data_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1829437'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H34 B2 N4'
_chemical_formula_weight         280.07

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   20.751(3)
_cell_length_b                   14.369(3)
_cell_length_c                   5.958(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.000(3)
_cell_angle_gamma                90
_cell_volume                     1776.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7631
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.64

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.047
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16409
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         28.768
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4544
_reflns_number_gt                4077
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.1818P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1683 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.7(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4544
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0926
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.85488(8) 0.21054(11) 0.2602(3) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.81186(8) 0.36581(11) 0.2784(3) 0.0156(3) Uani 1 1 d . . . . .
H2A H 0.8151 0.3731 0.4399 0.019 Uiso 1 1 calc R U . . .
H2B H 0.7745 0.4005 0.2274 0.019 Uiso 1 1 calc R U . . .
C3 C 0.75223(8) 0.24207(12) 0.0628(3) 0.0158(3) Uani 1 1 d . . . . .
H3 H 0.7542 0.1746 0.0403 0.019 Uiso 1 1 calc R U . . .
C4 C 0.76368(10) 0.28816(13) -0.1639(3) 0.0212(4) Uani 1 1 d . . . . .
H4A H 0.7592 0.3544 -0.1489 0.032 Uiso 1 1 d R U . . .
H4B H 0.7327 0.2655 -0.2703 0.032 Uiso 1 1 d R U . . .
H4C H 0.8063 0.2737 -0.2155 0.032 Uiso 1 1 d R U . . .
C5 C 0.68602(9) 0.26502(13) 0.1581(4) 0.0226(4) Uani 1 1 d . . . . .
H5A H 0.6811 0.2357 0.3019 0.034 Uiso 1 1 d R U . . .
H5B H 0.6533 0.2426 0.0578 0.034 Uiso 1 1 d R U . . .
H5C H 0.6819 0.3312 0.1746 0.034 Uiso 1 1 d R U . . .
C6 C 0.89822(9) 0.06219(11) 0.1441(3) 0.0166(3) Uani 1 1 d . . . . .
H6 H 0.9353 0.1029 0.1162 0.020 Uiso 1 1 calc R U . . .
C7 C 0.87244(10) 0.03026(14) -0.0827(3) 0.0256(4) Uani 1 1 d . . . . .
H7A H 0.8360 -0.0098 -0.0602 0.038 Uiso 1 1 d R U . . .
H7B H 0.9055 -0.0030 -0.1617 0.038 Uiso 1 1 d R U . . .
H7C H 0.8595 0.0835 -0.1691 0.038 Uiso 1 1 d R U . . .
C8 C 0.92177(10) -0.02044(12) 0.2817(3) 0.0242(4) Uani 1 1 d . . . . .
H8A H 0.9327 0.0000 0.4302 0.036 Uiso 1 1 d R U . . .
H8B H 0.9591 -0.0470 0.2113 0.036 Uiso 1 1 d R U . . .
H8C H 0.8883 -0.0664 0.2903 0.036 Uiso 1 1 d R U . . .
C9 C 0.96316(8) 0.21074(11) 0.4383(3) 0.0148(3) Uani 1 1 d . . . . .
H9 H 0.9492 0.1472 0.4736 0.018 Uiso 1 1 calc R U . . .
C10 C 0.96820(10) 0.26470(13) 0.6574(3) 0.0228(4) Uani 1 1 d . . . . .
H10A H 0.9823 0.3270 0.6268 0.034 Uiso 1 1 d R U . . .
H10B H 0.9987 0.2346 0.7546 0.034 Uiso 1 1 d R U . . .
H10C H 0.9268 0.2665 0.7290 0.034 Uiso 1 1 d R U . . .
C11 C 1.02887(9) 0.20521(13) 0.3237(3) 0.0207(4) Uani 1 1 d . . . . .
H11A H 1.0250 0.1705 0.1867 0.031 Uiso 1 1 d R U . . .
H11B H 1.0590 0.1748 0.4216 0.031 Uiso 1 1 d R U . . .
H11C H 1.0439 0.2669 0.2909 0.031 Uiso 1 1 d R U . . .
C12 C 0.86534(9) 0.49674(11) 0.0744(3) 0.0164(3) Uani 1 1 d . . . . .
H12 H 0.8228 0.5024 0.0042 0.020 Uiso 1 1 calc R U . . .
C13 C 0.86981(11) 0.57018(12) 0.2575(4) 0.0272(4) Uani 1 1 d . . . . .
H13A H 0.8368 0.5594 0.3673 0.041 Uiso 1 1 d R U . . .
H13B H 0.8641 0.6308 0.1926 0.041 Uiso 1 1 d R U . . .
H13C H 0.9113 0.5667 0.3281 0.041 Uiso 1 1 d R U . . .
C14 C 0.91558(11) 0.51241(13) -0.1065(4) 0.0278(5) Uani 1 1 d . . . . .
H14A H 0.9577 0.5123 -0.0401 0.042 Uiso 1 1 d R U . . .
H14B H 0.9080 0.5713 -0.1779 0.042 Uiso 1 1 d R U . . .
H14C H 0.9128 0.4636 -0.2160 0.042 Uiso 1 1 d R U . . .
B1 B 0.92395(9) 0.34746(13) 0.1999(3) 0.0149(4) Uani 1 1 d . . . . .
H1 H 0.9649 0.3684 0.1619 0.018 Uiso 1 1 d R U . . .
B2 B 0.78498(10) 0.06743(14) 0.3475(4) 0.0181(4) Uani 1 1 d . . . . .
N1 N 0.80398(7) 0.26752(9) 0.2229(3) 0.0143(3) Uani 1 1 d . . . . .
N2 N 0.91331(7) 0.25424(9) 0.2934(2) 0.0139(3) Uani 1 1 d . . . . .
N3 N 0.87007(7) 0.40250(9) 0.1712(3) 0.0142(3) Uani 1 1 d . . . . .
N4 N 0.84785(7) 0.11841(9) 0.2585(3) 0.0145(3) Uani 1 1 d . . . . .
H3B2 H 0.7563(11) 0.0403(16) 0.205(4) 0.028(6) Uiso 1 1 d . . . . .
H2B2 H 0.7577(11) 0.1174(15) 0.448(4) 0.024(6) Uiso 1 1 d . . . . .
H1B2 H 0.7996(12) 0.0095(16) 0.459(4) 0.031(6) Uiso 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 N4 1.332(2) . ?
C1 N1 1.355(2) . ?
C1 N2 1.380(2) . ?
C2 N1 1.460(2) . ?
C2 N3 1.465(2) . ?
C3 N1 1.482(2) . ?
C3 C5 1.523(2) . ?
C3 C4 1.523(3) . ?
C6 N4 1.487(2) . ?
C6 C8 1.524(2) . ?
C6 C7 1.524(3) . ?
C9 N2 1.485(2) . ?
C9 C10 1.522(3) . ?
C9 C11 1.527(2) . ?
C12 N3 1.475(2) . ?
C12 C14 1.516(3) . ?
C12 C13 1.521(3) . ?
B1 N3 1.380(2) . ?
B1 N2 1.467(2) . ?
B2 N4 1.587(2) . ?

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
N4 C1 N1 120.94(14) . . ?
N4 C1 N2 123.35(15) . . ?
N1 C1 N2 115.69(14) . . ?
N1 C2 N3 109.99(14) . . ?
N1 C3 C5 111.12(15) . . ?
N1 C3 C4 110.51(14) . . ?
C5 C3 C4 112.17(15) . . ?
N4 C6 C8 113.72(16) . . ?
N4 C6 C7 108.86(15) . . ?
C8 C6 C7 110.80(15) . . ?
N2 C9 C10 109.39(14) . . ?
N2 C9 C11 112.58(14) . . ?
C10 C9 C11 110.40(15) . . ?
N3 C12 C14 111.61(14) . . ?
N3 C12 C13 110.67(16) . . ?
C14 C12 C13 111.40(16) . . ?
N3 B1 N2 116.63(15) . . ?
C1 N1 C2 117.39(14) . . ?
C1 N1 C3 121.42(14) . . ?
C2 N1 C3 117.77(13) . . ?
C1 N2 B1 119.57(14) . . ?
C1 N2 C9 120.25(14) . . ?
B1 N2 C9 119.99(14) . . ?
B1 N3 C2 114.05(14) . . ?
B1 N3 C12 128.95(14) . . ?
C2 N3 C12 116.49(13) . . ?
C1 N4 C6 117.82(14) . . ?
C1 N4 B2 123.10(14) . . ?
C6 N4 B2 118.70(13) . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1829439'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H29 B N2 O2'
_chemical_formula_weight         292.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   11.490(2)
_cell_length_b                   12.061(3)
_cell_length_c                   12.206(3)
_cell_angle_alpha                89.223(3)
_cell_angle_beta                 86.315(3)
_cell_angle_gamma                81.499(3)
_cell_volume                     1669.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5167
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.41

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29204
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         26.449
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6870
_reflns_number_gt                4577
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0483P)²+0.4392P] 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         6870
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 1.19118(16) 0.28522(16) 0.83473(15) 0.0131(4) Uani 1 1 d . . . . .
H1 H 1.1792 0.3158 0.9048 0.016 Uiso 1 1 calc R U . . .
C2 C 1.24350(17) 0.31830(16) 0.64406(15) 0.0137(4) Uani 1 1 d . . . . .
C3 C 1.20623(17) 0.10937(16) 0.92949(15) 0.0148(4) Uani 1 1 d . . . . .
H3 H 1.1909 0.0347 0.9095 0.018 Uiso 1 1 calc R U . . .
C4 C 1.32748(18) 0.09444(18) 0.97493(17) 0.0209(5) Uani 1 1 d . . . . .
H4A H 1.3851 0.0606 0.9202 0.031 Uiso 1 1 calc R U . . .
H4B H 1.3278 0.0470 1.0387 0.031 Uiso 1 1 calc R U . . .
H4C H 1.3463 0.1662 0.9946 0.031 Uiso 1 1 calc R U . . .
C5 C 1.10848(18) 0.15617(18) 1.01334(16) 0.0210(5) Uani 1 1 d . . . . .
H5A H 1.1263 0.2247 1.0428 0.032 Uiso 1 1 calc R U . . .
H5B H 1.1022 0.1027 1.0716 0.032 Uiso 1 1 calc R U . . .
H5C H 1.0351 0.1707 0.9786 0.032 Uiso 1 1 calc R U . . .
C6 C 1.16247(17) 0.48039(16) 0.76452(16) 0.0150(4) Uani 1 1 d . . . . .
H6 H 1.1379 0.5143 0.6947 0.018 Uiso 1 1 calc R U . . .
C7 C 1.27115(18) 0.52856(17) 0.79377(17) 0.0211(5) Uani 1 1 d . . . . .
H7A H 1.2963 0.4982 0.8629 0.032 Uiso 1 1 calc R U . . .
H7B H 1.2527 0.6087 0.7991 0.032 Uiso 1 1 calc R U . . .
H7C H 1.3332 0.5093 0.7378 0.032 Uiso 1 1 calc R U . . .
C8 C 1.06026(19) 0.50930(18) 0.84945(18) 0.0264(5) Uani 1 1 d . . . . .
H8A H 0.9978 0.4680 0.8344 0.040 Uiso 1 1 calc R U . . .
H8B H 1.0320 0.5882 0.8463 0.040 Uiso 1 1 calc R U . . .
H8C H 1.0864 0.4900 0.9213 0.040 Uiso 1 1 calc R U . . .
C9 C 1.30272(17) 0.00509(16) 0.68446(16) 0.0148(4) Uani 1 1 d . . . . .
H9 H 1.3793 0.0080 0.7144 0.018 Uiso 1 1 calc R U . . .
C10 C 1.32095(17) -0.00754(17) 0.55814(16) 0.0175(4) Uani 1 1 d . . . . .
H10A H 1.3644 0.0507 0.5293 0.021 Uiso 1 1 calc R U . . .
H10B H 1.3688 -0.0792 0.5415 0.021 Uiso 1 1 calc R U . . .
C11 C 1.20623(17) -0.00043(17) 0.49933(16) 0.0175(4) Uani 1 1 d . . . . .
H11A H 1.1758 -0.0709 0.5097 0.021 Uiso 1 1 calc R U . . .
H11B H 1.2241 0.0087 0.4213 0.021 Uiso 1 1 calc R U . . .
C12 C 1.10881(17) 0.09550(16) 0.53803(15) 0.0157(4) Uani 1 1 d . . . . .
H12A H 1.1264 0.1647 0.5040 0.019 Uiso 1 1 calc R U . . .
H12B H 1.0346 0.0808 0.5120 0.019 Uiso 1 1 calc R U . . .
C13 C 1.09313(16) 0.11267(16) 0.66322(15) 0.0132(4) Uani 1 1 d . . . . .
H13 H 1.0408 0.1834 0.6778 0.016 Uiso 1 1 calc R U . . .
C14 C 1.04026(17) 0.01824(16) 0.72675(16) 0.0162(4) Uani 1 1 d . . . . .
H14A H 1.0244 0.0405 0.8029 0.019 Uiso 1 1 calc R U . . .
H14B H 0.9654 0.0107 0.6973 0.019 Uiso 1 1 calc R U . . .
C15 C 1.11834(17) -0.09693(16) 0.72266(17) 0.0184(5) Uani 1 1 d . . . . .
H15A H 1.1104 -0.1315 0.6527 0.022 Uiso 1 1 calc R U . . .
H15B H 1.0887 -0.1440 0.7798 0.022 Uiso 1 1 calc R U . . .
C16 C 1.25021(17) -0.09551(16) 0.73681(16) 0.0163(4) Uani 1 1 d . . . . .
H16A H 1.2941 -0.1639 0.7056 0.020 Uiso 1 1 calc R U . . .
H16B H 1.2624 -0.0967 0.8147 0.020 Uiso 1 1 calc R U . . .
C17 C 0.72247(16) 0.51557(16) 0.67861(15) 0.0130(4) Uani 1 1 d . . . . .
H17 H 0.7247 0.5461 0.6083 0.016 Uiso 1 1 calc R U . . .
C18 C 0.73785(16) 0.55207(16) 0.86913(15) 0.0133(4) Uani 1 1 d . . . . .
C19 C 0.80185(18) 0.34227(16) 0.59179(15) 0.0183(5) Uani 1 1 d . . . . .
H19 H 0.8239 0.2646 0.6159 0.022 Uiso 1 1 calc R U . . .
C20 C 0.91411(18) 0.38478(18) 0.54875(17) 0.0239(5) Uani 1 1 d . . . . .
H20A H 0.8949 0.4591 0.5195 0.036 Uiso 1 1 calc R U . . .
H20B H 0.9530 0.3359 0.4919 0.036 Uiso 1 1 calc R U . . .
H20C H 0.9654 0.3863 0.6076 0.036 Uiso 1 1 calc R U . . .
C21 C 0.7151(2) 0.34122(19) 0.50316(17) 0.0268(5) Uani 1 1 d . . . . .
H21A H 0.6471 0.3108 0.5327 0.040 Uiso 1 1 calc R U . . .
H21B H 0.7520 0.2958 0.4430 0.040 Uiso 1 1 calc R U . . .
H21C H 0.6916 0.4164 0.4778 0.040 Uiso 1 1 calc R U . . .
C22 C 0.65196(19) 0.70637(17) 0.74661(17) 0.0218(5) Uani 1 1 d . . . . .
H22 H 0.6202 0.7393 0.8173 0.026 Uiso 1 1 calc R U . . .
C23 C 0.7533(2) 0.7666(2) 0.7065(2) 0.0402(7) Uani 1 1 d . . . . .
H23A H 0.8153 0.7523 0.7562 0.060 Uiso 1 1 calc R U . . .
H23B H 0.7264 0.8458 0.7031 0.060 Uiso 1 1 calc R U . . .
H23C H 0.7825 0.7400 0.6347 0.060 Uiso 1 1 calc R U . . .
C24 C 0.5529(2) 0.7214(2) 0.66914(19) 0.0340(6) Uani 1 1 d . . . . .
H24A H 0.5836 0.6983 0.5967 0.051 Uiso 1 1 calc R U . . .
H24B H 0.5185 0.7989 0.6675 0.051 Uiso 1 1 calc R U . . .
H24C H 0.4939 0.6767 0.6941 0.051 Uiso 1 1 calc R U . . .
C25 C 0.78235(16) 0.23681(15) 0.84101(15) 0.0131(4) Uani 1 1 d . . . . .
H25 H 0.8668 0.2303 0.8198 0.016 Uiso 1 1 calc R U . . .
C26 C 0.73021(18) 0.14524(17) 0.78090(17) 0.0193(5) Uani 1 1 d . . . . .
H26A H 0.7597 0.1444 0.7046 0.023 Uiso 1 1 calc R U . . .
H26B H 0.7596 0.0731 0.8125 0.023 Uiso 1 1 calc R U . . .
C27 C 0.59504(18) 0.15751(18) 0.78441(18) 0.0241(5) Uani 1 1 d . . . . .
H27A H 0.5671 0.1271 0.8535 0.029 Uiso 1 1 calc R U . . .
H27B H 0.5727 0.1128 0.7259 0.029 Uiso 1 1 calc R U . . .
C28 C 0.53259(17) 0.27833(17) 0.77256(17) 0.0202(5) Uani 1 1 d . . . . .
H28A H 0.4496 0.2802 0.7941 0.024 Uiso 1 1 calc R U . . .
H28B H 0.5386 0.2997 0.6957 0.024 Uiso 1 1 calc R U . . .
C29 C 0.58106(16) 0.36570(16) 0.84028(15) 0.0138(4) Uani 1 1 d . . . . .
H29 H 0.5415 0.4404 0.8209 0.017 Uiso 1 1 calc R U . . .
C30 C 0.56175(16) 0.34886(16) 0.96529(16) 0.0161(4) Uani 1 1 d . . . . .
H30A H 0.5779 0.4154 1.0018 0.019 Uiso 1 1 calc R U . . .
H30B H 0.4793 0.3426 0.9821 0.019 Uiso 1 1 calc R U . . .
C31 C 0.63730(17) 0.24582(17) 1.01389(16) 0.0186(5) Uani 1 1 d . . . . .
H31A H 0.6365 0.2551 1.0928 0.022 Uiso 1 1 calc R U . . .
H31B H 0.6012 0.1799 1.0005 0.022 Uiso 1 1 calc R U . . .
C32 C 0.76607(17) 0.22523(16) 0.96738(16) 0.0169(4) Uani 1 1 d . . . . .
H32A H 0.8009 0.1504 0.9883 0.020 Uiso 1 1 calc R U . . .
H32B H 0.8090 0.2779 1.0009 0.020 Uiso 1 1 calc R U . . .
B1 B 1.22030(19) 0.12400(18) 0.70581(17) 0.0125(5) Uani 1 1 d . . . . .
B2 B 0.72045(19) 0.36063(18) 0.81132(17) 0.0122(5) Uani 1 1 d . . . . .
N1 N 1.20727(13) 0.17751(13) 0.82567(12) 0.0121(3) Uani 1 1 d . . . . .
N2 N 1.19079(14) 0.35664(13) 0.74736(12) 0.0130(4) Uani 1 1 d . . . . .
N3 N 0.74681(13) 0.40830(13) 0.69017(12) 0.0123(3) Uani 1 1 d . . . . .
N4 N 0.69370(14) 0.58538(13) 0.76579(12) 0.0127(4) Uani 1 1 d . . . . .
O1 O 1.27788(11) 0.21148(11) 0.63676(10) 0.0148(3) Uani 1 1 d . . . . .
O2 O 1.25791(12) 0.38538(11) 0.57062(11) 0.0206(3) Uani 1 1 d . . . . .
O3 O 0.77056(11) 0.44519(10) 0.88165(10) 0.0126(3) Uani 1 1 d . . . . .
O4 O 0.74705(12) 0.62311(11) 0.93696(11) 0.0180(3) 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 N1 1.290(2) . ?
C1 N2 1.362(2) . ?
C2 O2 1.219(2) . ?
C2 O1 1.293(2) . ?
C2 N2 1.416(2) . ?
C3 N1 1.501(2) . ?
C3 C4 1.518(3) . ?
C3 C5 1.519(3) . ?
C6 N2 1.495(2) . ?
C6 C7 1.517(3) . ?
C6 C8 1.519(3) . ?
C9 C16 1.546(3) . ?
C9 C10 1.549(3) . ?
C9 B1 1.612(3) . ?
C10 C11 1.532(3) . ?
C11 C12 1.542(3) . ?
C12 C13 1.540(3) . ?
C13 C14 1.545(3) . ?
C13 B1 1.607(3) . ?
C14 C15 1.538(3) . ?
C15 C16 1.539(3) . ?
C17 N3 1.290(2) . ?
C17 N4 1.359(2) . ?
C18 O4 1.220(2) . ?
C18 O3 1.298(2) . ?
C18 N4 1.421(2) . ?
C19 N3 1.502(2) . ?
C19 C20 1.518(3) . ?
C19 C21 1.518(3) . ?
C22 N4 1.487(2) . ?
C22 C23 1.514(3) . ?
C22 C24 1.515(3) . ?
C25 C26 1.546(3) . ?
C25 C32 1.549(3) . ?
C25 B2 1.604(3) . ?
C26 C27 1.536(3) . ?
C27 C28 1.535(3) . ?
C28 C29 1.536(3) . ?
C29 C30 1.543(3) . ?
C29 B2 1.610(3) . ?
C30 C31 1.542(3) . ?
C31 C32 1.536(3) . ?
B1 O1 1.540(2) . ?
B1 N1 1.596(3) . ?
B2 O3 1.539(2) . ?
B2 N3 1.606(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 123.63(18) . . ?
O2 C2 O1 124.39(18) . . ?
O2 C2 N2 119.92(17) . . ?
O1 C2 N2 115.63(16) . . ?
N1 C3 C4 109.73(15) . . ?
N1 C3 C5 112.91(15) . . ?
C4 C3 C5 112.96(16) . . ?
N2 C6 C7 110.70(15) . . ?
N2 C6 C8 111.39(16) . . ?
C7 C6 C8 112.03(17) . . ?
C16 C9 C10 111.00(16) . . ?
C16 C9 B1 113.69(16) . . ?
C10 C9 B1 105.94(15) . . ?
C11 C10 C9 114.14(16) . . ?
C10 C11 C12 114.97(16) . . ?
C13 C12 C11 115.10(15) . . ?
C12 C13 C14 114.31(16) . . ?
C12 C13 B1 107.45(15) . . ?
C14 C13 B1 110.08(15) . . ?
C15 C14 C13 115.02(16) . . ?
C14 C15 C16 115.53(16) . . ?
C15 C16 C9 116.06(15) . . ?
N3 C17 N4 122.20(17) . . ?
O4 C18 O3 124.75(17) . . ?
O4 C18 N4 119.65(17) . . ?
O3 C18 N4 115.53(16) . . ?
N3 C19 C20 110.83(17) . . ?
N3 C19 C21 111.61(16) . . ?
C20 C19 C21 112.04(17) . . ?
N4 C22 C23 110.86(18) . . ?
N4 C22 C24 110.82(17) . . ?
C23 C22 C24 112.20(19) . . ?
C26 C25 C32 111.94(16) . . ?
C26 C25 B2 112.16(16) . . ?
C32 C25 B2 106.26(15) . . ?
C27 C26 C25 116.12(17) . . ?
C26 C27 C28 114.73(17) . . ?
C27 C28 C29 114.96(16) . . ?
C28 C29 C30 113.22(16) . . ?
C28 C29 B2 110.01(16) . . ?
C30 C29 B2 107.97(15) . . ?
C31 C30 C29 115.63(16) . . ?
C32 C31 C30 114.57(16) . . ?
C31 C32 C25 114.63(16) . . ?
O1 B1 N1 102.38(15) . . ?
O1 B1 C13 110.41(15) . . ?
N1 B1 C13 110.68(16) . . ?
O1 B1 C9 106.60(16) . . ?
N1 B1 C9 119.46(16) . . ?
C13 B1 C9 107.02(16) . . ?
O3 B2 C25 108.48(15) . . ?
O3 B2 N3 100.86(14) . . ?
C25 B2 N3 118.10(16) . . ?
O3 B2 C29 110.36(16) . . ?
C25 B2 C29 107.36(16) . . ?
N3 B2 C29 111.44(15) . . ?
C1 N1 C3 117.66(16) . . ?
C1 N1 B1 118.73(15) . . ?
C3 N1 B1 123.53(15) . . ?
C1 N2 C2 120.27(16) . . ?
C1 N2 C6 120.23(16) . . ?
C2 N2 C6 117.82(15) . . ?
C17 N3 C19 117.26(16) . . ?
C17 N3 B2 115.70(15) . . ?
C19 N3 B2 126.96(15) . . ?
C17 N4 C18 118.98(15) . . ?
C17 N4 C22 119.57(16) . . ?
C18 N4 C22 118.47(15) . . ?
C2 O1 B1 123.50(16) . . ?
C18 O3 B2 120.26(14) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1829438'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H44 B2 N2'
_chemical_formula_weight         370.22

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

_space_group_crystal_system      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                   9.8852(7)
_cell_length_b                   15.1771(9)
_cell_length_c                   16.6307(12)
_cell_angle_alpha                69.154(2)
_cell_angle_beta                 84.904(2)
_cell_angle_gamma                79.674(2)
_cell_volume                     2293.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11518
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.38

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.482
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42373
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_av_R_equivalents  0.1103
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9420
_reflns_number_gt                6494
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0836P)²+0.6482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9420
_refine_ls_number_parameters     503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1603
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.1903(2) 0.29222(14) 0.69170(12) 0.0223(4) Uani 1 1 d . . . . .
H1 H 0.0949 0.2983 0.6952 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4247(2) 0.22679(15) 0.56538(13) 0.0276(5) Uani 1 1 d . . . . .
H2 H 0.3544 0.2818 0.5384 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5675(2) 0.25299(16) 0.53055(13) 0.0320(5) Uani 1 1 d . . . . .
H3A H 0.5765 0.2579 0.4706 0.038 Uiso 1 1 calc R U . . .
H3B H 0.5718 0.3155 0.5326 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6905(2) 0.18265(17) 0.57870(14) 0.0342(5) Uani 1 1 d . . . . .
H4A H 0.7701 0.2151 0.5654 0.041 Uiso 1 1 calc R U . . .
H4B H 0.7103 0.1304 0.5566 0.041 Uiso 1 1 calc R U . . .
C5 C 0.6724(2) 0.14045(15) 0.67714(13) 0.0283(5) Uani 1 1 d . . . . .
H5A H 0.6899 0.1867 0.7013 0.034 Uiso 1 1 calc R U . . .
H5B H 0.7415 0.0842 0.6986 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5297(2) 0.11256(14) 0.71033(13) 0.0235(4) Uani 1 1 d . . . . .
H6 H 0.5237 0.0962 0.7730 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5094(2) 0.02508(15) 0.68846(14) 0.0321(5) Uani 1 1 d . . . . .
H7A H 0.5902 -0.0233 0.7060 0.038 Uiso 1 1 calc R U . . .
H7B H 0.4316 -0.0011 0.7224 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4852(3) 0.04462(17) 0.59341(16) 0.0401(6) Uani 1 1 d . . . . .
H8A H 0.5735 0.0442 0.5630 0.048 Uiso 1 1 calc R U . . .
H8B H 0.4442 -0.0071 0.5895 0.048 Uiso 1 1 calc R U . . .
C9 C 0.3927(3) 0.13925(18) 0.54791(14) 0.0379(6) Uani 1 1 d . . . . .
H9A H 0.2979 0.1320 0.5656 0.045 Uiso 1 1 calc R U . . .
H9B H 0.4008 0.1520 0.4864 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1941(2) 0.12176(15) 0.74261(15) 0.0303(5) Uani 1 1 d . . . . .
H10 H 0.2354 0.0757 0.7150 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2266(3) 0.07618(18) 0.83782(16) 0.0477(7) Uani 1 1 d . . . . .
H11A H 0.3245 0.0632 0.8443 0.071 Uiso 1 1 d R U . . .
H11B H 0.1895 0.0176 0.8624 0.071 Uiso 1 1 d R U . . .
H11C H 0.1862 0.1194 0.8669 0.071 Uiso 1 1 d R U . . .
C12 C 0.0402(2) 0.14031(19) 0.7292(2) 0.0505(7) Uani 1 1 d . . . . .
H12A H -0.0047 0.1766 0.7636 0.076 Uiso 1 1 d R U . . .
H12B H 0.0062 0.0807 0.7460 0.076 Uiso 1 1 d R U . . .
H12C H 0.0217 0.1757 0.6696 0.076 Uiso 1 1 d R U . . .
C13 C 0.0101(2) 0.46523(17) 0.66502(16) 0.0386(6) Uani 1 1 d . . . . .
H13A H -0.0291 0.4318 0.6359 0.058 Uiso 1 1 d R U . . .
H13B H -0.0365 0.5300 0.6488 0.058 Uiso 1 1 d R U . . .
H13C H 0.0001 0.4343 0.7261 0.058 Uiso 1 1 d R U . . .
C14 C 0.1617(2) 0.46429(14) 0.64041(13) 0.0250(4) Uani 1 1 d . . . . .
H14 H 0.1953 0.5063 0.6646 0.030 Uiso 1 1 calc R U . . .
C15 C 0.1827(3) 0.50521(18) 0.54304(14) 0.0405(6) Uani 1 1 d . . . . .
H15A H 0.2782 0.5097 0.5292 0.061 Uiso 1 1 d R U . . .
H15B H 0.1287 0.5675 0.5206 0.061 Uiso 1 1 d R U . . .
H15C H 0.1547 0.4637 0.5178 0.061 Uiso 1 1 d R U . . .
C16 C 0.4976(2) 0.43300(14) 0.65138(12) 0.0227(4) Uani 1 1 d . . . . .
H16 H 0.4869 0.4528 0.5891 0.027 Uiso 1 1 calc R U . . .
C17 C 0.4574(2) 0.52130(14) 0.67937(14) 0.0290(5) Uani 1 1 d . . . . .
H17A H 0.5291 0.5608 0.6591 0.035 Uiso 1 1 calc R U . . .
H17B H 0.3736 0.5583 0.6509 0.035 Uiso 1 1 calc R U . . .
C18 C 0.4348(2) 0.50003(16) 0.77689(14) 0.0318(5) Uani 1 1 d . . . . .
H18A H 0.5236 0.4894 0.8023 0.038 Uiso 1 1 calc R U . . .
H18B H 0.3809 0.5561 0.7857 0.038 Uiso 1 1 calc R U . . .
C19 C 0.3623(2) 0.41380(15) 0.82506(13) 0.0273(5) Uani 1 1 d . . . . .
H19A H 0.2651 0.4318 0.8129 0.033 Uiso 1 1 calc R U . . .
H19B H 0.3713 0.3979 0.8864 0.033 Uiso 1 1 calc R U . . .
C20 C 0.4179(2) 0.32435(13) 0.80180(12) 0.0213(4) Uani 1 1 d . . . . .
H20 H 0.3610 0.2751 0.8319 0.026 Uiso 1 1 calc R U . . .
C21 C 0.5685(2) 0.28299(15) 0.82568(13) 0.0273(5) Uani 1 1 d . . . . .
H21A H 0.5882 0.2194 0.8223 0.033 Uiso 1 1 calc R U . . .
H21B H 0.5789 0.2764 0.8851 0.033 Uiso 1 1 calc R U . . .
C22 C 0.6770(2) 0.34152(16) 0.76975(14) 0.0305(5) Uani 1 1 d . . . . .
H22A H 0.6848 0.3917 0.7916 0.037 Uiso 1 1 calc R U . . .
H22B H 0.7652 0.3000 0.7766 0.037 Uiso 1 1 calc R U . . .
C23 C 0.6481(2) 0.38755(15) 0.67312(13) 0.0268(4) Uani 1 1 d . . . . .
H23A H 0.6747 0.3392 0.6467 0.032 Uiso 1 1 calc R U . . .
H23B H 0.7059 0.4364 0.6475 0.032 Uiso 1 1 calc R U . . .
C24 C 0.2469(2) 0.21284(14) 1.15933(12) 0.0233(4) Uani 1 1 d . . . . .
H24 H 0.3418 0.2077 1.1506 0.028 Uiso 1 1 calc R U . . .
C25 C -0.0053(2) 0.34691(15) 1.04664(13) 0.0275(5) Uani 1 1 d . . . . .
H25 H 0.0583 0.3772 1.0662 0.033 Uiso 1 1 calc R U . . .
C26 C -0.1536(2) 0.39336(16) 1.06000(15) 0.0364(5) Uani 1 1 d . . . . .
H26A H -0.1624 0.3969 1.1174 0.044 Uiso 1 1 calc R U . . .
H26B H -0.1680 0.4583 1.0194 0.044 Uiso 1 1 calc R U . . .
C27 C -0.2678(2) 0.34233(19) 1.04952(17) 0.0436(6) Uani 1 1 d . . . . .
H27A H -0.3523 0.3653 1.0753 0.052 Uiso 1 1 calc R U . . .
H27B H -0.2828 0.3597 0.9886 0.052 Uiso 1 1 calc R U . . .
C28 C -0.2389(2) 0.23320(18) 1.08966(16) 0.0371(5) Uani 1 1 d . . . . .
H28A H -0.3042 0.2071 1.0679 0.045 Uiso 1 1 calc R U . . .
H28B H -0.2545 0.2151 1.1514 0.045 Uiso 1 1 calc R U . . .
C29 C -0.0918(2) 0.18740(16) 1.07189(13) 0.0293(5) Uani 1 1 d . . . . .
H29 H -0.0793 0.1188 1.1051 0.035 Uiso 1 1 calc R U . . .
C30 C -0.0696(3) 0.20185(19) 0.97482(15) 0.0403(6) Uani 1 1 d . . . . .
H30A H 0.0096 0.1567 0.9682 0.048 Uiso 1 1 calc R U . . .
H30B H -0.1490 0.1863 0.9554 0.048 Uiso 1 1 calc R U . . .
C31 C -0.0473(3) 0.3026(2) 0.91532(15) 0.0470(7) Uani 1 1 d . . . . .
H31A H 0.0011 0.2975 0.8634 0.056 Uiso 1 1 calc R U . . .
H31B H -0.1367 0.3409 0.8986 0.056 Uiso 1 1 calc R U . . .
C32 C 0.0325(2) 0.35642(17) 0.95244(14) 0.0372(6) Uani 1 1 d . . . . .
H32A H 0.0167 0.4236 0.9172 0.045 Uiso 1 1 calc R U . . .
H32B H 0.1300 0.3332 0.9483 0.045 Uiso 1 1 calc R U . . .
C33 C 0.2459(2) 0.13818(16) 1.05289(13) 0.0300(5) Uani 1 1 d . . . . .
H33 H 0.2026 0.1675 0.9967 0.036 Uiso 1 1 calc R U . . .
C34 C 0.2232(3) 0.03459(17) 1.08849(16) 0.0436(6) Uani 1 1 d . . . . .
H34A H 0.2674 0.0028 1.1427 0.065 Uiso 1 1 d R U . . .
H34B H 0.2614 0.0034 1.0486 0.065 Uiso 1 1 d R U . . .
H34C H 0.1263 0.0321 1.0965 0.065 Uiso 1 1 d R U . . .
C35 C 0.3985(3) 0.1449(2) 1.03764(17) 0.0481(7) Uani 1 1 d . . . . .
H35A H 0.4106 0.2107 1.0188 0.072 Uiso 1 1 d R U . . .
H35B H 0.4348 0.1184 0.9942 0.072 Uiso 1 1 d R U . . .
H35C H 0.4464 0.1100 1.0902 0.072 Uiso 1 1 d R U . . .
C36 C 0.2680(2) 0.29243(16) 1.25882(14) 0.0297(5) Uani 1 1 d . . . . .
H36 H 0.2344 0.2799 1.3185 0.036 Uiso 1 1 calc R U . . .
C37 C 0.2353(3) 0.39937(18) 1.2128(2) 0.0516(7) Uani 1 1 d . . . . .
H37A H 0.2756 0.4154 1.1557 0.077 Uiso 1 1 d R U . . .
H37B H 0.2728 0.4315 1.2439 0.077 Uiso 1 1 d R U . . .
H37C H 0.1375 0.4190 1.2095 0.077 Uiso 1 1 d R U . . .
C38 C 0.4217(2) 0.25766(19) 1.26219(18) 0.0444(6) Uani 1 1 d . . . . .
H38A H 0.4380 0.1892 1.2869 0.067 Uiso 1 1 d R U . . .
H38B H 0.4623 0.2840 1.2971 0.067 Uiso 1 1 d R U . . .
H38C H 0.4621 0.2774 1.2052 0.067 Uiso 1 1 d R U . . .
C39 C -0.0597(2) 0.28028(13) 1.30214(12) 0.0228(4) Uani 1 1 d . . . . .
H39 H -0.0626 0.3482 1.2682 0.027 Uiso 1 1 calc R U . . .
C40 C -0.2045(2) 0.25398(14) 1.30660(13) 0.0273(5) Uani 1 1 d . . . . .
H40A H -0.2657 0.2884 1.3382 0.033 Uiso 1 1 calc R U . . .
H40B H -0.2379 0.2759 1.2485 0.033 Uiso 1 1 calc R U . . .
C41 C -0.2134(2) 0.14756(15) 1.34873(14) 0.0288(5) Uani 1 1 d . . . . .
H41A H -0.3006 0.1367 1.3345 0.035 Uiso 1 1 calc R U . . .
H41B H -0.2132 0.1309 1.4107 0.035 Uiso 1 1 calc R U . . .
C42 C -0.0972(2) 0.08018(14) 1.32240(13) 0.0269(5) Uani 1 1 d . . . . .
H42A H -0.1198 0.0773 1.2679 0.032 Uiso 1 1 calc R U . . .
H42B H -0.0945 0.0166 1.3649 0.032 Uiso 1 1 calc R U . . .
C43 C 0.0476(2) 0.10757(13) 1.31320(12) 0.0224(4) Uani 1 1 d . . . . .
H43 H 0.1089 0.0686 1.2847 0.027 Uiso 1 1 calc R U . . .
C44 C 0.1105(2) 0.09337(15) 1.39981(13) 0.0287(5) Uani 1 1 d . . . . .
H44A H 0.1150 0.0269 1.4362 0.034 Uiso 1 1 calc R U . . .
H44B H 0.2039 0.1070 1.3887 0.034 Uiso 1 1 calc R U . . .
C45 C 0.0316(2) 0.15538(16) 1.44883(13) 0.0314(5) Uani 1 1 d . . . . .
H45A H 0.0884 0.1521 1.4948 0.038 Uiso 1 1 calc R U . . .
H45B H -0.0503 0.1287 1.4753 0.038 Uiso 1 1 calc R U . . .
C46 C -0.0117(2) 0.26091(16) 1.39420(14) 0.0314(5) Uani 1 1 d . . . . .
H46A H 0.0654 0.2942 1.3893 0.038 Uiso 1 1 calc R U . . .
H46B H -0.0858 0.2882 1.4247 0.038 Uiso 1 1 calc R U . . .
B1 B 0.4145(2) 0.20300(15) 0.66738(14) 0.0199(4) Uani 1 1 d . . . . .
B2 B 0.4014(2) 0.35312(15) 0.70001(13) 0.0188(4) Uani 1 1 d . . . . .
B3 B 0.0173(2) 0.23513(16) 1.10225(13) 0.0220(5) Uani 1 1 d . . . . .
B4 B 0.0433(2) 0.21780(15) 1.25504(13) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.26289(16) 0.20733(11) 0.70398(10) 0.0215(4) Uani 1 1 d . . . . .
N2 N 0.24765(16) 0.36895(11) 0.67463(10) 0.0199(3) Uani 1 1 d . . . . .
N3 N 0.17421(16) 0.19006(12) 1.10952(10) 0.0223(4) Uani 1 1 d . . . . .
N4 N 0.18919(16) 0.24282(11) 1.22134(10) 0.0216(4) Uani 1 1 d . . . . .
H1B1 H 0.456(2) 0.2754(14) 0.6777(12) 0.017(5) Uiso 1 1 d . . . . .
H1B3 H -0.019(2) 0.2305(14) 1.1820(13) 0.020(5) Uiso 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 N1 1.313(2) . ?
C1 N2 1.315(3) . ?
C2 C3 1.542(3) . ?
C2 C9 1.546(3) . ?
C2 B1 1.601(3) . ?
C3 C4 1.536(3) . ?
C4 C5 1.538(3) . ?
C5 C6 1.544(3) . ?
C6 C7 1.545(3) . ?
C6 B1 1.605(3) . ?
C7 C8 1.534(3) . ?
C8 C9 1.533(4) . ?
C10 N1 1.486(3) . ?
C10 C12 1.518(3) . ?
C10 C11 1.523(3) . ?
C13 C14 1.517(3) . ?
C14 N2 1.483(2) . ?
C14 C15 1.524(3) . ?
C16 C23 1.540(3) . ?
C16 C17 1.546(3) . ?
C16 B2 1.614(3) . ?
C17 C18 1.540(3) . ?
C18 C19 1.535(3) . ?
C19 C20 1.537(3) . ?
C20 C21 1.536(3) . ?
C20 B2 1.606(3) . ?
C21 C22 1.543(3) . ?
C22 C23 1.537(3) . ?
C24 N3 1.311(3) . ?
C24 N4 1.316(3) . ?
C25 C32 1.539(3) . ?
C25 C26 1.542(3) . ?
C25 B3 1.602(3) . ?
C26 C27 1.533(3) . ?
C27 C28 1.532(4) . ?
C28 C29 1.546(3) . ?
C29 C30 1.551(3) . ?
C29 B3 1.606(3) . ?
C30 C31 1.541(4) . ?
C31 C32 1.531(4) . ?
C33 N3 1.490(2) . ?
C33 C34 1.521(3) . ?
C33 C35 1.523(3) . ?
C36 N4 1.481(3) . ?
C36 C37 1.515(3) . ?
C36 C38 1.515(3) . ?
C39 C40 1.543(3) . ?
C39 C46 1.554(3) . ?
C39 B4 1.610(3) . ?
C40 C41 1.530(3) . ?
C41 C42 1.538(3) . ?
C42 C43 1.541(3) . ?
C43 C44 1.548(3) . ?
C43 B4 1.602(3) . ?
C44 C45 1.526(3) . ?
C45 C46 1.537(3) . ?
B1 N1 1.566(3) . ?
B2 N2 1.568(3) . ?
B3 N3 1.575(3) . ?
B4 N4 1.562(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 122.44(17) . . ?
C3 C2 C9 113.53(18) . . ?
C3 C2 B1 109.73(17) . . ?
C9 C2 B1 107.55(17) . . ?
C4 C3 C2 115.41(17) . . ?
C3 C4 C5 115.89(17) . . ?
C4 C5 C6 115.33(17) . . ?
C5 C6 C7 110.22(16) . . ?
C5 C6 B1 108.37(16) . . ?
C7 C6 B1 111.38(17) . . ?
C8 C7 C6 115.50(18) . . ?
C9 C8 C7 114.85(18) . . ?
C8 C9 C2 115.19(19) . . ?
N1 C10 C12 114.60(19) . . ?
N1 C10 C11 109.08(17) . . ?
C12 C10 C11 111.3(2) . . ?
N2 C14 C13 114.22(17) . . ?
N2 C14 C15 109.52(17) . . ?
C13 C14 C15 110.96(18) . . ?
C23 C16 C17 110.49(16) . . ?
C23 C16 B2 108.03(15) . . ?
C17 C16 B2 111.04(16) . . ?
C18 C17 C16 115.72(17) . . ?
C19 C18 C17 115.27(17) . . ?
C18 C19 C20 114.40(17) . . ?
C21 C20 C19 113.88(16) . . ?
C21 C20 B2 110.01(16) . . ?
C19 C20 B2 107.33(15) . . ?
C20 C21 C22 115.84(16) . . ?
C23 C22 C21 115.74(16) . . ?
C22 C23 C16 115.07(17) . . ?
N3 C24 N4 121.83(18) . . ?
C32 C25 C26 113.74(17) . . ?
C32 C25 B3 107.09(17) . . ?
C26 C25 B3 110.44(17) . . ?
C27 C26 C25 115.75(19) . . ?
C28 C27 C26 114.81(19) . . ?
C27 C28 C29 114.72(19) . . ?
C28 C29 C30 110.39(18) . . ?
C28 C29 B3 108.92(18) . . ?
C30 C29 B3 110.45(17) . . ?
C31 C30 C29 115.9(2) . . ?
C32 C31 C30 116.48(19) . . ?
C31 C32 C25 114.89(19) . . ?
N3 C33 C34 109.86(17) . . ?
N3 C33 C35 113.99(18) . . ?
C34 C33 C35 111.1(2) . . ?
N4 C36 C37 109.80(18) . . ?
N4 C36 C38 114.72(18) . . ?
C37 C36 C38 111.6(2) . . ?
C40 C39 C46 110.11(16) . . ?
C40 C39 B4 108.18(16) . . ?
C46 C39 B4 111.11(16) . . ?
C41 C40 C39 115.35(17) . . ?
C40 C41 C42 115.14(16) . . ?
C41 C42 C43 115.73(16) . . ?
C42 C43 C44 113.99(16) . . ?
C42 C43 B4 110.18(16) . . ?
C44 C43 B4 106.86(16) . . ?
C45 C44 C43 114.70(17) . . ?
C44 C45 C46 115.15(17) . . ?
C45 C46 C39 115.69(17) . . ?
N1 B1 C2 113.12(16) . . ?
N1 B1 C6 120.97(16) . . ?
C2 B1 C6 107.88(16) . . ?
N2 B2 C20 112.56(15) . . ?
N2 B2 C16 120.36(16) . . ?
C20 B2 C16 107.85(15) . . ?
N3 B3 C25 112.16(16) . . ?
N3 B3 C29 120.83(17) . . ?
C25 B3 C29 107.81(17) . . ?
N4 B4 C43 112.55(16) . . ?
N4 B4 C39 121.25(16) . . ?
C43 B4 C39 107.70(15) . . ?
C1 N1 C10 119.04(16) . . ?
C1 N1 B1 117.31(16) . . ?
C10 N1 B1 123.29(15) . . ?
C1 N2 C14 119.00(16) . . ?
C1 N2 B2 117.01(15) . . ?
C14 N2 B2 123.75(15) . . ?
C24 N3 C33 119.32(17) . . ?
C24 N3 B3 116.46(16) . . ?
C33 N3 B3 123.40(16) . . ?
C24 N4 C36 119.00(16) . . ?
C24 N4 B4 117.19(16) . . ?
C36 N4 B4 123.69(16) . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.072

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_Compound4
_database_code_depnum_ccdc_archive 'CCDC 1829440'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H31 B N2 O'
_chemical_formula_weight         278.24

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.8250(5)
_cell_length_b                   18.6367(8)
_cell_length_c                   19.5807(7)
_cell_angle_alpha                90
_cell_angle_beta                 126.909(2)
_cell_angle_gamma                90
_cell_volume                     3450.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    25014
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      23.37

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            94778
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.1841
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         28.756
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8940
_reflns_number_gt                6814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0884P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8940
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1456
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.13627(12) 0.15974(6) 0.37171(7) 0.0160(2) Uani 1 1 d . . . . .
H1 H 0.0844 0.1423 0.3161 0.019 Uiso 1 1 calc R U . . .
C2 C 0.23238(12) 0.26187(6) 0.46874(7) 0.0162(2) Uani 1 1 d . . . . .
H2A H 0.2756 0.3054 0.4670 0.019 Uiso 1 1 calc R U . . .
H2B H 0.1764 0.2745 0.4882 0.019 Uiso 1 1 calc R U . . .
C3 C 0.62117(12) 0.20435(6) 0.08754(7) 0.0161(2) Uani 1 1 d . . . . .
H3 H 0.5501 0.2383 0.0677 0.019 Uiso 1 1 calc R U . . .
C4 C 0.76056(13) 0.10575(7) 0.18263(8) 0.0215(2) Uani 1 1 d . . . . .
H4A H 0.8003 0.0960 0.2418 0.026 Uiso 1 1 calc R U . . .
H4B H 0.7238 0.0611 0.1511 0.026 Uiso 1 1 calc R U . . .
C5 C 0.41419(12) 0.09443(6) 0.60532(7) 0.0184(2) Uani 1 1 d . . . . .
H5 H 0.4783 0.0849 0.5903 0.022 Uiso 1 1 calc R U . . .
C6 C 0.37254(14) 0.02206(7) 0.62336(8) 0.0271(3) Uani 1 1 d . . . . .
H6A H 0.3564 -0.0125 0.5813 0.032 Uiso 1 1 calc R U . . .
H6B H 0.4522 0.0051 0.6789 0.032 Uiso 1 1 calc R U . . .
C7 C 0.24058(16) 0.02322(8) 0.62210(9) 0.0340(3) Uani 1 1 d . . . . .
H7A H 0.2014 -0.0248 0.6097 0.041 Uiso 1 1 calc R U . . .
H7B H 0.2703 0.0358 0.6787 0.041 Uiso 1 1 calc R U . . .
C8 C 0.12317(14) 0.07521(7) 0.55751(9) 0.0272(3) Uani 1 1 d . . . . .
H8A H 0.0573 0.0807 0.5712 0.033 Uiso 1 1 calc R U . . .
H8B H 0.0719 0.0540 0.5011 0.033 Uiso 1 1 calc R U . . .
C9 C 0.17486(12) 0.14996(6) 0.55457(7) 0.0172(2) Uani 1 1 d . . . . .
H9 H 0.0928 0.1779 0.5097 0.021 Uiso 1 1 calc R U . . .
C10 C 0.25129(15) 0.19260(7) 0.63909(8) 0.0243(3) Uani 1 1 d . . . . .
H10A H 0.2604 0.2420 0.6276 0.029 Uiso 1 1 calc R U . . .
H10B H 0.1919 0.1924 0.6580 0.029 Uiso 1 1 calc R U . . .
C11 C 0.39924(15) 0.16483(7) 0.71291(8) 0.0269(3) Uani 1 1 d . . . . .
H11A H 0.4481 0.2024 0.7555 0.032 Uiso 1 1 calc R U . . .
H11B H 0.3879 0.1244 0.7395 0.032 Uiso 1 1 calc R U . . .
C12 C 0.49217(13) 0.14142(7) 0.68637(7) 0.0224(2) Uani 1 1 d . . . . .
H12A H 0.5726 0.1149 0.7331 0.027 Uiso 1 1 calc R U . . .
H12B H 0.5281 0.1839 0.6766 0.027 Uiso 1 1 calc R U . . .
C13 C 0.20686(13) 0.03798(6) 0.41022(7) 0.0209(2) Uani 1 1 d . . . . .
H13 H 0.2408 0.0079 0.4602 0.025 Uiso 1 1 calc R U . . .
C14 C 0.06358(14) 0.00824(6) 0.33650(8) 0.0258(3) Uani 1 1 d . . . . .
H14A H -0.0036 0.0146 0.3484 0.039 Uiso 1 1 d R U . . .
H14B H 0.0727 -0.0419 0.3296 0.039 Uiso 1 1 d R U . . .
H14C H 0.0316 0.0333 0.2850 0.039 Uiso 1 1 d R U . . .
C15 C 0.31567(15) 0.03231(8) 0.39238(9) 0.0326(3) Uani 1 1 d . . . . .
H15A H 0.2849 0.0600 0.3426 0.049 Uiso 1 1 d R U . . .
H15B H 0.3257 -0.0171 0.3829 0.049 Uiso 1 1 d R U . . .
H15C H 0.4051 0.0502 0.4406 0.049 Uiso 1 1 d R U . . .
C16 C 0.05239(13) 0.27790(6) 0.30702(7) 0.0191(2) Uani 1 1 d . . . . .
H16 H -0.0047 0.2471 0.2566 0.023 Uiso 1 1 calc R U . . .
C17 C 0.14334(16) 0.32498(9) 0.29449(9) 0.0336(3) Uani 1 1 d . . . . .
H17A H 0.1963 0.3580 0.3413 0.050 Uiso 1 1 d R U . . .
H17B H 0.0839 0.3512 0.2420 0.050 Uiso 1 1 d R U . . .
H17C H 0.2074 0.2954 0.2921 0.050 Uiso 1 1 d R U . . .
C18 C -0.04877(15) 0.32222(8) 0.31340(9) 0.0300(3) Uani 1 1 d . . . . .
H18A H -0.1036 0.2909 0.3220 0.045 Uiso 1 1 d R U . . .
H18B H -0.1108 0.3488 0.2615 0.045 Uiso 1 1 d R U . . .
H18C H 0.0039 0.3549 0.3606 0.045 Uiso 1 1 d R U . . .
C19 C 0.95198(12) 0.17496(6) 0.09448(7) 0.0168(2) Uani 1 1 d . . . . .
H19 H 0.9857 0.2199 0.1269 0.020 Uiso 1 1 calc R U . . .
C20 C 0.92287(13) 0.18769(6) 0.00710(8) 0.0202(2) Uani 1 1 d . . . . .
H20A H 0.8788 0.2344 -0.0139 0.024 Uiso 1 1 calc R U . . .
H20B H 1.0129 0.1894 0.0161 0.024 Uiso 1 1 calc R U . . .
C21 C 0.82843(14) 0.13151(7) -0.06301(8) 0.0242(3) Uani 1 1 d . . . . .
H21A H 0.7838 0.1543 -0.1182 0.029 Uiso 1 1 calc R U . . .
H21B H 0.8889 0.0936 -0.0585 0.029 Uiso 1 1 calc R U . . .
C22 C 0.71257(13) 0.09702(7) -0.06128(7) 0.0219(2) Uani 1 1 d . . . . .
H22A H 0.6792 0.0542 -0.0964 0.026 Uiso 1 1 calc R U . . .
H22B H 0.6336 0.1301 -0.0869 0.026 Uiso 1 1 calc R U . . .
C23 C 0.75836(12) 0.07653(6) 0.02805(7) 0.0175(2) Uani 1 1 d . . . . .
H23 H 0.6753 0.0586 0.0225 0.021 Uiso 1 1 calc R U . . .
C24 C 0.87468(14) 0.01836(6) 0.07308(8) 0.0238(3) Uani 1 1 d . . . . .
H24A H 0.8807 0.0007 0.1218 0.029 Uiso 1 1 calc R U . . .
H24B H 0.8456 -0.0215 0.0339 0.029 Uiso 1 1 calc R U . . .
C25 C 1.02359(14) 0.04237(7) 0.10448(8) 0.0257(3) Uani 1 1 d . . . . .
H25A H 1.0919 0.0076 0.1458 0.031 Uiso 1 1 calc R U . . .
H25B H 1.0274 0.0419 0.0564 0.031 Uiso 1 1 calc R U . . .
C26 C 1.06780(12) 0.11722(7) 0.14563(7) 0.0214(2) Uani 1 1 d . . . . .
H26A H 1.1517 0.1321 0.1514 0.026 Uiso 1 1 calc R U . . .
H26B H 1.0924 0.1142 0.2026 0.026 Uiso 1 1 calc R U . . .
C27 C 0.65665(13) 0.26386(6) -0.00596(8) 0.0204(2) Uani 1 1 d . . . . .
H27 H 0.6942 0.2495 -0.0370 0.024 Uiso 1 1 calc R U . . .
C28 C 0.49816(15) 0.27550(9) -0.07277(9) 0.0343(3) Uani 1 1 d . . . . .
H28A H 0.4536 0.2307 -0.1001 0.051 Uiso 1 1 d R U . . .
H28B H 0.4827 0.3092 -0.1147 0.051 Uiso 1 1 d R U . . .
H28C H 0.4585 0.2940 -0.0456 0.051 Uiso 1 1 d R U . . .
C29 C 0.7332(2) 0.33252(7) 0.04186(11) 0.0412(4) Uani 1 1 d . . . . .
H29A H 0.6983 0.3491 0.0725 0.062 Uiso 1 1 d R U . . .
H29B H 0.7169 0.3686 0.0019 0.062 Uiso 1 1 d R U . . .
H29C H 0.8328 0.3232 0.0814 0.062 Uiso 1 1 d R U . . .
C30 C 0.54960(13) 0.15557(6) 0.17197(8) 0.0197(2) Uani 1 1 d . . . . .
H30 H 0.4792 0.1937 0.1408 0.024 Uiso 1 1 calc R U . . .
C31 C 0.62863(16) 0.16998(8) 0.26707(9) 0.0294(3) Uani 1 1 d . . . . .
H31A H 0.6956 0.1322 0.2994 0.044 Uiso 1 1 d R U . . .
H31B H 0.5624 0.1718 0.2802 0.044 Uiso 1 1 d R U . . .
H31C H 0.6776 0.2150 0.2816 0.044 Uiso 1 1 d R U . . .
C32 C 0.47040(16) 0.08421(8) 0.14551(10) 0.0336(3) Uani 1 1 d . . . . .
H32A H 0.4251 0.0758 0.0859 0.050 Uiso 1 1 d R U . . .
H32B H 0.4002 0.0859 0.1555 0.050 Uiso 1 1 d R U . . .
H32C H 0.5359 0.0461 0.1785 0.050 Uiso 1 1 d R U . . .
B1 B 0.28221(13) 0.14206(6) 0.52984(7) 0.0127(2) Uani 1 1 d . . . . .
B2 B 0.81625(13) 0.14737(6) 0.08847(7) 0.0139(2) Uani 1 1 d . . . . .
N1 N 0.20086(10) 0.11297(5) 0.43403(6) 0.01542(19) Uani 1 1 d . . . . .
N2 N 0.13960(11) 0.23072(5) 0.38236(6) 0.0168(2) Uani 1 1 d . . . . .
N3 N 0.69129(10) 0.20497(5) 0.05513(6) 0.01499(18) Uani 1 1 d . . . . .
N4 N 0.64512(10) 0.15816(5) 0.14714(6) 0.01704(19) Uani 1 1 d . . . . .
O1 O 0.33709(8) 0.21385(4) 0.52553(5) 0.01489(16) Uani 1 1 d . . . . .
O2 O 0.86490(9) 0.13176(5) 0.17778(5) 0.01777(17) 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 N1 1.3088(14) . ?
C1 N2 1.3360(13) . ?
C1 H1 0.9300 . ?
C2 O1 1.3845(13) . ?
C2 N2 1.4740(13) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N3 1.3123(14) . ?
C3 N4 1.3366(13) . ?
C3 H3 0.9300 . ?
C4 O2 1.3809(14) . ?
C4 N4 1.4700(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C12 1.5422(16) . ?
C5 C6 1.5477(17) . ?
C5 B1 1.6241(16) . ?
C5 H5 0.9800 . ?
C6 C7 1.546(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.5351(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.5362(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.5463(17) . ?
C9 B1 1.6143(17) . ?
C9 H9 0.9800 . ?
C10 C11 1.5429(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.5341(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.4885(13) . ?
C13 C15 1.5260(19) . ?
C13 C14 1.5244(16) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N2 1.4784(13) . ?
C16 C17 1.5178(18) . ?
C16 C18 1.5193(17) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C26 1.5457(16) . ?
C19 C20 1.5474(15) . ?
C19 B2 1.6210(16) . ?
C19 H19 0.9800 . ?
C20 C21 1.5449(17) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.5320(17) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.5366(15) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.5453(17) . ?
C23 B2 1.6244(16) . ?
C23 H23 0.9800 . ?
C24 C25 1.5423(18) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.5369(17) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 N3 1.4884(14) . ?
C27 C29 1.5217(19) . ?
C27 C28 1.5251(18) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 N4 1.4745(14) . ?
C30 C31 1.5240(17) . ?
C30 C32 1.5270(18) . ?
C30 H30 0.9800 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9601 . ?
C32 H32B 0.9601 . ?
C32 H32C 0.9601 . ?
B1 O1 1.5113(14) . ?
B1 N1 1.6034(14) . ?
B2 O2 1.5052(13) . ?
B2 N3 1.6135(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
N1 C1 N2 124.60(10) . . ?
N1 C1 H1 117.7 . . ?
N2 C1 H1 117.7 . . ?
O1 C2 N2 110.94(9) . . ?
O1 C2 H2A 109.5 . . ?
N2 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
N3 C3 N4 124.31(10) . . ?
N3 C3 H3 117.8 . . ?
N4 C3 H3 117.8 . . ?
O2 C4 N4 110.41(9) . . ?
O2 C4 H4A 109.6 . . ?
N4 C4 H4A 109.6 . . ?
O2 C4 H4B 109.6 . . ?
N4 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C12 C5 C6 109.60(10) . . ?
C12 C5 B1 106.26(9) . . ?
C6 C5 B1 114.86(10) . . ?
C12 C5 H5 108.7 . . ?
C6 C5 H5 108.7 . . ?
B1 C5 H5 108.7 . . ?
C7 C6 C5 116.15(10) . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 C6 115.26(10) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 114.82(11) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 114.58(10) . . ?
C8 C9 B1 109.32(10) . . ?
C10 C9 B1 107.97(9) . . ?
C8 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
B1 C9 H9 108.3 . . ?
C11 C10 C9 115.80(10) . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C10 114.71(9) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C5 113.76(10) . . ?
C11 C12 H12A 108.8 . . ?
C5 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C5 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N1 C13 C15 110.00(10) . . ?
N1 C13 C14 113.77(10) . . ?
C15 C13 C14 111.62(11) . . ?
N1 C13 H13 107.0 . . ?
C15 C13 H13 107.0 . . ?
C14 C13 H13 107.0 . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.3 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.7 . . ?
C13 C15 H15B 109.3 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.4 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 C17 111.58(10) . . ?
N2 C16 C18 110.69(10) . . ?
C17 C16 C18 111.61(11) . . ?
N2 C16 H16 107.6 . . ?
C17 C16 H16 107.6 . . ?
C18 C16 H16 107.6 . . ?
C16 C17 H17A 109.6 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.3 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.4 . . ?
C16 C18 H18B 109.4 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.7 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C26 C19 C20 110.21(9) . . ?
C26 C19 B2 106.23(9) . . ?
C20 C19 B2 114.54(9) . . ?
C26 C19 H19 108.6 . . ?
C20 C19 H19 108.6 . . ?
B2 C19 H19 108.6 . . ?
C21 C20 C19 116.15(9) . . ?
C21 C20 H20A 108.2 . . ?
C19 C20 H20A 108.2 . . ?
C21 C20 H20B 108.2 . . ?
C19 C20 H20B 108.2 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C20 116.33(10) . . ?
C22 C21 H21A 108.2 . . ?
C20 C21 H21A 108.2 . . ?
C22 C21 H21B 108.2 . . ?
C20 C21 H21B 108.2 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 C23 114.89(10) . . ?
C21 C22 H22A 108.5 . . ?
C23 C22 H22A 108.5 . . ?
C21 C22 H22B 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 C24 114.10(10) . . ?
C22 C23 B2 109.48(9) . . ?
C24 C23 B2 108.25(9) . . ?
C22 C23 H23 108.3 . . ?
C24 C23 H23 108.3 . . ?
B2 C23 H23 108.3 . . ?
C25 C24 C23 115.84(10) . . ?
C25 C24 H24A 108.3 . . ?
C23 C24 H24A 108.3 . . ?
C25 C24 H24B 108.3 . . ?
C23 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
C26 C25 C24 114.82(10) . . ?
C26 C25 H25A 108.6 . . ?
C24 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C24 C25 H25B 108.6 . . ?
H25A C25 H25B 107.5 . . ?
C25 C26 C19 113.71(10) . . ?
C25 C26 H26A 108.8 . . ?
C19 C26 H26A 108.8 . . ?
C25 C26 H26B 108.8 . . ?
C19 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
N3 C27 C29 110.53(10) . . ?
N3 C27 C28 113.43(10) . . ?
C29 C27 C28 112.25(12) . . ?
N3 C27 H27 106.7 . . ?
C29 C27 H27 106.7 . . ?
C28 C27 H27 106.7 . . ?
C27 C28 H28A 109.6 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.6 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.4 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N4 C30 C31 111.60(10) . . ?
N4 C30 C32 110.59(10) . . ?
C31 C30 C32 111.67(11) . . ?
N4 C30 H30 107.6 . . ?
C31 C30 H30 107.6 . . ?
C32 C30 H30 107.6 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.4 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.6 . . ?
C30 C32 H32B 109.3 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O1 B1 N1 102.13(8) . . ?
O1 B1 C9 112.17(9) . . ?
N1 B1 C9 110.76(9) . . ?
O1 B1 C5 108.94(9) . . ?
N1 B1 C5 116.96(9) . . ?
C9 B1 C5 106.01(9) . . ?
O2 B2 N3 102.52(8) . . ?
O2 B2 C19 107.83(9) . . ?
N3 B2 C19 116.40(9) . . ?
O2 B2 C23 112.89(9) . . ?
N3 B2 C23 111.29(9) . . ?
C19 B2 C23 106.05(9) . . ?
C1 N1 C13 116.37(9) . . ?
C1 N1 B1 118.02(9) . . ?
C13 N1 B1 125.17(8) . . ?
C1 N2 C2 120.06(9) . . ?
C1 N2 C16 119.71(9) . . ?
C2 N2 C16 120.21(9) . . ?
C3 N3 C27 116.50(9) . . ?
C3 N3 B2 119.32(9) . . ?
C27 N3 B2 123.98(9) . . ?
C3 N4 C4 119.37(9) . . ?
C3 N4 C30 120.42(9) . . ?
C4 N4 C30 120.01(9) . . ?
C2 O1 B1 114.22(8) . . ?
C4 O2 B2 114.45(9) . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-3

