# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Compound11
_database_code_depnum_ccdc_archive 'CCDC 1554011'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H58 B2 N4'
_chemical_formula_weight         604.51

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.906(3)
_cell_length_b                   11.690(3)
_cell_length_c                   21.696(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.946(4)
_cell_angle_gamma                90
_cell_volume                     3522.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    41650
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.72

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_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  0.714
_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            85145
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         28.733
_diffrn_reflns_theta_full        25.240
_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             9116
_reflns_number_gt                7810
_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    'Mercury 3.8'
_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)+(0.0715P)²+2.5367P] 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         9116
_refine_ls_number_parameters     413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
B1 B 0.60338(10) 0.35166(12) 0.18402(6) 0.0160(3) Uani 1 1 d . . . . .
B2 B 0.35252(9) 0.10748(11) 0.13087(6) 0.0138(2) Uani 1 1 d . . . . .
C1 C 0.44068(8) 0.27799(10) 0.16010(5) 0.0117(2) Uani 1 1 d . . . . .
C2 C 0.31717(8) 0.22135(10) 0.09162(5) 0.0139(2) Uani 1 1 d . . . . .
C3 C 0.41781(9) 0.40017(11) 0.06514(6) 0.0165(2) Uani 1 1 d . . . . .
H3 H 0.4771 0.4357 0.0824 0.020 Uiso 1 1 calc R U . . .
C4 C 0.43763(10) 0.35766(13) 0.00025(6) 0.0237(3) Uani 1 1 d . . . . .
H4A H 0.4905 0.3048 0.0026 0.036 Uiso 1 1 d R U . . .
H4B H 0.4535 0.4215 -0.0252 0.036 Uiso 1 1 d R U . . .
H4C H 0.3813 0.3201 -0.0174 0.036 Uiso 1 1 d R U . . .
C5 C 0.33846(10) 0.49121(12) 0.06460(7) 0.0249(3) Uani 1 1 d . . . . .
H5A H 0.2851 0.4672 0.0378 0.037 Uiso 1 1 d R U . . .
H5B H 0.3633 0.5624 0.0500 0.037 Uiso 1 1 d R U . . .
H5C H 0.3174 0.5011 0.1057 0.037 Uiso 1 1 d R U . . .
C6 C 0.45078(9) 0.44158(11) 0.23030(6) 0.0178(2) Uani 1 1 d . . . . .
H6 H 0.3821 0.4227 0.2260 0.021 Uiso 1 1 calc R U . . .
C7 C 0.48109(10) 0.43008(12) 0.29888(6) 0.0227(3) Uani 1 1 d . . . . .
H7A H 0.4720 0.3525 0.3119 0.034 Uiso 1 1 d R U . . .
H7B H 0.4426 0.4802 0.3225 0.034 Uiso 1 1 d R U . . .
H7C H 0.5477 0.4505 0.3052 0.034 Uiso 1 1 d R U . . .
C8 C 0.46133(11) 0.56480(12) 0.20826(7) 0.0251(3) Uani 1 1 d . . . . .
H8A H 0.5260 0.5906 0.2177 0.038 Uiso 1 1 d R U . . .
H8B H 0.4170 0.6128 0.2288 0.038 Uiso 1 1 d R U . . .
H8C H 0.4476 0.5685 0.1645 0.038 Uiso 1 1 d R U . . .
C9 C 0.68139(9) 0.43646(12) 0.21393(6) 0.0195(2) Uani 1 1 d . . . . .
H9 H 0.6503 0.4892 0.2418 0.023 Uiso 1 1 calc R U . . .
C10 C 0.72236(11) 0.50492(13) 0.15998(7) 0.0261(3) Uani 1 1 d . . . . .
H10A H 0.6722 0.5548 0.1427 0.031 Uiso 1 1 calc R U . . .
H10B H 0.7743 0.5531 0.1765 0.031 Uiso 1 1 calc R U . . .
C11 C 0.76043(10) 0.43223(14) 0.10761(7) 0.0266(3) Uani 1 1 d . . . . .
H11A H 0.8219 0.3993 0.1214 0.032 Uiso 1 1 calc R U . . .
H11B H 0.7715 0.4815 0.0727 0.032 Uiso 1 1 calc R U . . .
C12 C 0.75761(11) 0.36403(16) 0.25128(7) 0.0322(3) Uani 1 1 d . . . . .
H12A H 0.7279 0.3330 0.2872 0.039 Uiso 1 1 calc R U . . .
H12B H 0.8093 0.4144 0.2660 0.039 Uiso 1 1 calc R U . . .
C13 C 0.80219(13) 0.26356(17) 0.21552(9) 0.0409(4) Uani 1 1 d . . . . .
H13A H 0.8506 0.2942 0.1895 0.049 Uiso 1 1 calc R U . . .
H13B H 0.8345 0.2124 0.2451 0.049 Uiso 1 1 calc R U . . .
C14 C 0.73159(10) 0.19546(13) 0.17606(8) 0.0302(3) Uani 1 1 d . . . . .
H14A H 0.7007 0.1409 0.2023 0.036 Uiso 1 1 calc R U . . .
H14B H 0.7673 0.1519 0.1468 0.036 Uiso 1 1 calc R U . . .
C15 C 0.65180(9) 0.26338(12) 0.13948(7) 0.0220(3) Uani 1 1 d . . . . .
H15 H 0.6028 0.2102 0.1225 0.026 Uiso 1 1 calc R U . . .
C16 C 0.69185(10) 0.33545(14) 0.08634(7) 0.0269(3) Uani 1 1 d . . . . .
H16A H 0.7256 0.2848 0.0594 0.032 Uiso 1 1 calc R U . . .
H16B H 0.6381 0.3684 0.0623 0.032 Uiso 1 1 calc R U . . .
C17 C 0.42467(8) 0.15641(10) 0.24813(5) 0.0135(2) Uani 1 1 d . . . . .
C18 C 0.34278(9) 0.17224(10) 0.28125(5) 0.0156(2) Uani 1 1 d . . . . .
H18 H 0.2862 0.1981 0.2611 0.019 Uiso 1 1 calc R U . . .
C19 C 0.34477(10) 0.14961(11) 0.34430(6) 0.0193(2) Uani 1 1 d . . . . .
H19 H 0.2896 0.1614 0.3660 0.023 Uiso 1 1 calc R U . . .
C20 C 0.42824(10) 0.10958(12) 0.37537(6) 0.0239(3) Uani 1 1 d . . . . .
C21 C 0.51007(10) 0.09532(14) 0.34151(7) 0.0270(3) Uani 1 1 d . . . . .
H21 H 0.5669 0.0701 0.3616 0.032 Uiso 1 1 calc R U . . .
C22 C 0.50892(9) 0.11785(12) 0.27832(6) 0.0214(3) Uani 1 1 d . . . . .
H22 H 0.5642 0.1071 0.2566 0.026 Uiso 1 1 calc R U . . .
C23 C 0.42957(14) 0.07976(17) 0.44316(7) 0.0385(4) Uani 1 1 d . . . . .
H23A H 0.4206 -0.0012 0.4479 0.058 Uiso 1 1 d R U . . .
H23B H 0.3786 0.1199 0.4621 0.058 Uiso 1 1 d R U . . .
H23C H 0.4903 0.1018 0.4626 0.058 Uiso 1 1 d R U . . .
C24 C 0.28220(9) 0.00864(11) 0.15493(6) 0.0172(2) Uani 1 1 d . . . . .
H24 H 0.2348 0.0441 0.1809 0.021 Uiso 1 1 calc R U . . .
C25 C 0.22805(9) -0.04775(11) 0.09869(6) 0.0206(3) Uani 1 1 d . . . . .
H25A H 0.1885 -0.1094 0.1134 0.025 Uiso 1 1 calc R U . . .
H25B H 0.1851 0.0085 0.0793 0.025 Uiso 1 1 calc R U . . .
C26 C 0.29286(10) -0.09623(13) 0.04948(7) 0.0273(3) Uani 1 1 d . . . . .
H26A H 0.3201 -0.1681 0.0643 0.033 Uiso 1 1 calc R U . . .
H26B H 0.2534 -0.1123 0.0123 0.033 Uiso 1 1 calc R U . . .
C27 C 0.37539(10) -0.01615(13) 0.03294(7) 0.0259(3) Uani 1 1 d . . . . .
H27A H 0.3493 0.0435 0.0059 0.031 Uiso 1 1 calc R U . . .
H27B H 0.4211 -0.0595 0.0101 0.031 Uiso 1 1 calc R U . . .
C28 C 0.42963(9) 0.04043(11) 0.08855(6) 0.0184(2) Uani 1 1 d . . . . .
H28 H 0.4736 0.0976 0.0727 0.022 Uiso 1 1 calc R U . . .
C29 C 0.48957(10) -0.04372(12) 0.12929(7) 0.0264(3) Uani 1 1 d . . . . .
H29A H 0.5298 0.0000 0.1585 0.032 Uiso 1 1 calc R U . . .
H29B H 0.5319 -0.0857 0.1033 0.032 Uiso 1 1 calc R U . . .
C30 C 0.43105(12) -0.13041(12) 0.16546(8) 0.0311(3) Uani 1 1 d . . . . .
H30A H 0.4727 -0.1628 0.1982 0.037 Uiso 1 1 calc R U . . .
H30B H 0.4111 -0.1923 0.1379 0.037 Uiso 1 1 calc R U . . .
C31 C 0.34083(10) -0.08056(12) 0.19424(7) 0.0243(3) Uani 1 1 d . . . . .
H31A H 0.3608 -0.0451 0.2333 0.029 Uiso 1 1 calc R U . . .
H31B H 0.2983 -0.1435 0.2033 0.029 Uiso 1 1 calc R U . . .
C32 C 0.15958(9) 0.21523(11) 0.04377(6) 0.0186(2) Uani 1 1 d . . . . .
C33 C 0.12713(11) 0.17746(14) -0.01551(6) 0.0267(3) Uani 1 1 d . . . . .
C34 C 0.03178(12) 0.14221(16) -0.02439(8) 0.0368(4) Uani 1 1 d . . . . .
H34 H 0.0099 0.1151 -0.0629 0.044 Uiso 1 1 calc R U . . .
C35 C -0.03099(12) 0.14676(17) 0.02289(9) 0.0403(4) Uani 1 1 d . . . . .
H35 H -0.0939 0.1209 0.0165 0.048 Uiso 1 1 calc R U . . .
C36 C 0.00023(10) 0.19006(15) 0.07997(8) 0.0310(3) Uani 1 1 d . . . . .
H36 H -0.0430 0.1955 0.1112 0.037 Uiso 1 1 calc R U . . .
C37 C 0.09524(9) 0.22559(12) 0.09146(6) 0.0205(3) Uani 1 1 d . . . . .
C38 C 0.12576(10) 0.27819(13) 0.15287(6) 0.0257(3) Uani 1 1 d . . . . .
H38A H 0.0702 0.2895 0.1766 0.039 Uiso 1 1 d R U . . .
H38B H 0.1562 0.3505 0.1462 0.039 Uiso 1 1 d R U . . .
H38C H 0.1703 0.2282 0.1748 0.039 Uiso 1 1 d R U . . .
C39 C 0.19323(13) 0.17672(19) -0.06823(7) 0.0406(4) Uani 1 1 d . . . . .
H39A H 0.2372 0.1137 -0.0633 0.061 Uiso 1 1 d R U . . .
H39B H 0.2288 0.2471 -0.0686 0.061 Uiso 1 1 d R U . . .
H39C H 0.1560 0.1686 -0.1065 0.061 Uiso 1 1 d R U . . .
N1 N 0.41622(7) 0.17827(8) 0.18283(4) 0.01262(19) Uani 1 1 d . . . . .
N2 N 0.39632(7) 0.30161(9) 0.10474(5) 0.0138(2) Uani 1 1 d . . . . .
N3 N 0.25345(8) 0.25991(10) 0.05269(5) 0.0181(2) Uani 1 1 d . . . . .
N4 N 0.50282(7) 0.35704(8) 0.19133(5) 0.01292(19) 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
B1 N4 1.4168(16) . ?
B1 C9 1.5838(18) . ?
B1 C15 1.5872(19) . ?
B2 C24 1.6175(17) . ?
B2 N1 1.6241(16) . ?
B2 C2 1.6418(18) . ?
B2 C28 1.6458(18) . ?
C1 N1 1.3172(15) . ?
C1 N2 1.3502(15) . ?
C1 N4 1.4141(15) . ?
C2 N3 1.2747(16) . ?
C2 N2 1.4631(15) . ?
C3 N2 1.4770(15) . ?
C3 C4 1.5313(18) . ?
C3 C5 1.5326(19) . ?
C6 N4 1.5093(15) . ?
C6 C8 1.5272(19) . ?
C6 C7 1.5315(18) . ?
C9 C10 1.5504(19) . ?
C9 C12 1.552(2) . ?
C10 C11 1.535(2) . ?
C11 C16 1.535(2) . ?
C12 C13 1.554(3) . ?
C13 C14 1.498(3) . ?
C14 C15 1.549(2) . ?
C15 C16 1.554(2) . ?
C17 C22 1.3879(17) . ?
C17 C18 1.3897(16) . ?
C17 N1 1.4386(14) . ?
C18 C19 1.3921(17) . ?
C19 C20 1.3930(19) . ?
C20 C21 1.396(2) . ?
C20 C23 1.5106(19) . ?
C21 C22 1.3953(19) . ?
C24 C25 1.5479(18) . ?
C24 C31 1.5518(19) . ?
C25 C26 1.5402(19) . ?
C26 C27 1.538(2) . ?
C27 C28 1.5390(19) . ?
C28 C29 1.539(2) . ?
C29 C30 1.540(2) . ?
C30 C31 1.544(2) . ?
C32 C37 1.4075(18) . ?
C32 N3 1.4101(16) . ?
C32 C33 1.4117(18) . ?
C33 C34 1.392(2) . ?
C33 C39 1.504(2) . ?
C34 C35 1.382(3) . ?
C35 C36 1.387(2) . ?
C36 C37 1.3952(19) . ?
C37 C38 1.5084(19) . ?

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 B1 C9 125.84(11) . . ?
N4 B1 C15 123.30(11) . . ?
C9 B1 C15 110.69(11) . . ?
C24 B2 N1 117.21(10) . . ?
C24 B2 C2 125.22(10) . . ?
N1 B2 C2 94.88(9) . . ?
C24 B2 C28 105.18(10) . . ?
N1 B2 C28 106.39(9) . . ?
C2 B2 C28 106.44(10) . . ?
N1 C1 N2 113.52(10) . . ?
N1 C1 N4 124.20(10) . . ?
N2 C1 N4 122.18(10) . . ?
N3 C2 N2 113.11(11) . . ?
N3 C2 B2 144.08(11) . . ?
N2 C2 B2 102.52(9) . . ?
N2 C3 C4 109.45(10) . . ?
N2 C3 C5 112.27(10) . . ?
C4 C3 C5 112.45(11) . . ?
N4 C6 C8 112.68(10) . . ?
N4 C6 C7 111.77(10) . . ?
C8 C6 C7 111.16(11) . . ?
C10 C9 C12 114.09(12) . . ?
C10 C9 B1 106.52(11) . . ?
C12 C9 B1 107.90(12) . . ?
C11 C10 C9 115.30(12) . . ?
C10 C11 C16 113.45(11) . . ?
C9 C12 C13 115.52(13) . . ?
C14 C13 C12 114.86(14) . . ?
C13 C14 C15 116.84(13) . . ?
C14 C15 C16 112.54(11) . . ?
C14 C15 B1 109.65(12) . . ?
C16 C15 B1 106.18(11) . . ?
C11 C16 C15 114.67(12) . . ?
C22 C17 C18 119.57(11) . . ?
C22 C17 N1 123.14(11) . . ?
C18 C17 N1 117.26(10) . . ?
C17 C18 C19 120.48(11) . . ?
C18 C19 C20 120.89(12) . . ?
C19 C20 C21 117.83(12) . . ?
C19 C20 C23 121.13(14) . . ?
C21 C20 C23 121.02(13) . . ?
C22 C21 C20 121.75(12) . . ?
C17 C22 C21 119.46(12) . . ?
C25 C24 C31 111.57(11) . . ?
C25 C24 B2 109.12(10) . . ?
C31 C24 B2 110.37(10) . . ?
C26 C25 C24 115.14(11) . . ?
C27 C26 C25 114.09(11) . . ?
C26 C27 C28 114.85(12) . . ?
C29 C28 C27 113.88(11) . . ?
C29 C28 B2 109.46(10) . . ?
C27 C28 B2 109.57(10) . . ?
C28 C29 C30 115.37(12) . . ?
C29 C30 C31 114.80(12) . . ?
C30 C31 C24 116.50(12) . . ?
C37 C32 N3 119.09(11) . . ?
C37 C32 C33 120.74(12) . . ?
N3 C32 C33 119.42(12) . . ?
C34 C33 C32 118.43(14) . . ?
C34 C33 C39 120.53(14) . . ?
C32 C33 C39 121.04(13) . . ?
C35 C34 C33 121.28(15) . . ?
C34 C35 C36 119.76(14) . . ?
C35 C36 C37 121.23(15) . . ?
C36 C37 C32 118.35(13) . . ?
C36 C37 C38 120.01(13) . . ?
C32 C37 C38 121.59(12) . . ?
C1 N1 C17 121.09(10) . . ?
C1 N1 B2 109.46(9) . . ?
C17 N1 B2 127.38(9) . . ?
C1 N2 C2 110.28(9) . . ?
C1 N2 C3 125.46(10) . . ?
C2 N2 C3 124.03(10) . . ?
C2 N3 C32 124.54(11) . . ?
C1 N4 B1 119.98(10) . . ?
C1 N4 C6 113.42(9) . . ?
B1 N4 C6 126.59(10) . . ?

_refine_diff_density_max         1.777
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.057

_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_Compound16a
_database_code_depnum_ccdc_archive 'CCDC 1554012'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H56 B N3 O'
_chemical_formula_weight         557.64

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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'

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

_cell_length_a                   16.181(4)
_cell_length_b                   16.181(3)
_cell_length_c                   12.989(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3401.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4773
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      20.49

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'
_exptl_absorpt_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            36391
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.1418
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.372
_diffrn_reflns_theta_max         21.568
_diffrn_reflns_theta_full        21.568
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3937
_reflns_number_gt                3211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury 3.8'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0527P)²] 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 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3937
_refine_ls_number_parameters     374
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.3663(3) 0.2134(3) 0.6228(4) 0.0246(13) Uani 1 1 d . . . . .
H1 H 0.319033 0.178346 0.640416 0.029 Uiso 1 1 calc R U . . .
C1A C 0.3167(3) 0.2501(3) 0.3478(4) 0.0244(12) Uani 1 1 d . . . . .
H1A H 0.287997 0.216333 0.296379 0.029 Uiso 1 1 calc R U . . .
C1B C 0.2061(3) 0.1873(3) 0.4926(4) 0.0253(12) Uani 1 1 d . . . . .
H1B H 0.208669 0.138434 0.536958 0.030 Uiso 1 1 calc R U . . .
C2 C 0.4166(3) 0.1035(3) 0.5215(4) 0.0227(12) Uani 1 1 d . . . . .
C2A C 0.4077(3) 0.2546(3) 0.3164(4) 0.0329(14) Uani 1 1 d . . . . .
H2A1 H 0.437926 0.285978 0.367679 0.040 Uiso 1 1 calc R U . . .
H2A2 H 0.430460 0.199211 0.314722 0.040 Uiso 1 1 calc R U . . .
C2B C 0.1471(3) 0.1659(3) 0.4041(4) 0.0316(14) Uani 1 1 d . . . . .
H2B1 H 0.142985 0.213066 0.358305 0.038 Uiso 1 1 calc R U . . .
H2B2 H 0.170038 0.120249 0.365161 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5208(3) 0.1998(3) 0.5988(4) 0.0305(14) Uani 1 1 d . . . . .
H3 H 0.509274 0.259174 0.593991 0.037 Uiso 1 1 calc R U . . .
C3A C 0.4195(4) 0.2949(4) 0.2115(5) 0.0521(18) Uani 1 1 d . . . . .
H3A1 H 0.478035 0.297865 0.195805 0.062 Uiso 1 1 calc R U . . .
H3A2 H 0.393236 0.261150 0.159109 0.062 Uiso 1 1 calc R U . . .
C3B C 0.0611(3) 0.1426(4) 0.4404(5) 0.0463(17) Uani 1 1 d . . . . .
H3B1 H 0.063975 0.092541 0.481394 0.056 Uiso 1 1 calc R U . . .
H3B2 H 0.026145 0.131640 0.381295 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5761(3) 0.1799(3) 0.5085(4) 0.0378(14) Uani 1 1 d . . . . .
H4A H 0.627285 0.209371 0.515434 0.057 Uiso 1 1 calc R U . . .
H4B H 0.586809 0.121613 0.506950 0.057 Uiso 1 1 calc R U . . .
H4C H 0.549272 0.196217 0.445777 0.057 Uiso 1 1 calc R U . . .
C4A C 0.3827(5) 0.3814(4) 0.2089(5) 0.067(2) Uani 1 1 d . . . . .
H4A1 H 0.388409 0.404340 0.140309 0.080 Uiso 1 1 calc R U . . .
H4A2 H 0.412593 0.416788 0.256379 0.080 Uiso 1 1 calc R U . . .
C4B C 0.0234(3) 0.2119(4) 0.5046(5) 0.0520(17) Uani 1 1 d . . . . .
H4B1 H 0.015133 0.260268 0.461685 0.062 Uiso 1 1 calc R U . . .
H4B2 H -0.030062 0.194569 0.530634 0.062 Uiso 1 1 calc R U . . .
C5 C 0.5652(3) 0.1877(3) 0.7016(4) 0.0437(16) Uani 1 1 d . . . . .
H5A H 0.617869 0.214942 0.699423 0.066 Uiso 1 1 calc R U . . .
H5B H 0.532412 0.210782 0.756037 0.066 Uiso 1 1 calc R U . . .
H5C H 0.573227 0.129733 0.713768 0.066 Uiso 1 1 calc R U . . .
C5A C 0.2920(4) 0.3790(4) 0.2387(5) 0.0514(17) Uani 1 1 d . . . . .
H5A1 H 0.261217 0.349010 0.186621 0.062 Uiso 1 1 calc R U . . .
H5A2 H 0.270537 0.434912 0.241541 0.062 Uiso 1 1 calc R U . . .
C5B C 0.0797(3) 0.2335(4) 0.5939(5) 0.0532(18) Uani 1 1 d . . . . .
H5B1 H 0.083368 0.186670 0.640231 0.064 Uiso 1 1 calc R U . . .
H5B2 H 0.056217 0.279516 0.631860 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5087(3) -0.0107(3) 0.5854(5) 0.0364(15) Uani 1 1 d . . . . .
H6 H 0.546212 0.027459 0.620711 0.044 Uiso 1 1 calc R U . . .
C6A C 0.2799(3) 0.3374(3) 0.3428(4) 0.0362(14) Uani 1 1 d . . . . .
H6A1 H 0.221262 0.334328 0.357689 0.043 Uiso 1 1 calc R U . . .
H6A2 H 0.305453 0.371192 0.395689 0.043 Uiso 1 1 calc R U . . .
C7 C 0.5594(4) -0.0755(4) 0.5317(6) 0.073(2) Uani 1 1 d . . . . .
H7A H 0.589811 -0.106770 0.581719 0.109 Uiso 1 1 calc R U . . .
H7B H 0.523500 -0.111777 0.493953 0.109 Uiso 1 1 calc R U . . .
H7C H 0.597205 -0.049315 0.484980 0.109 Uiso 1 1 calc R U . . .
C8 C 0.4508(4) -0.0479(4) 0.6641(6) 0.075(2) Uani 1 1 d . . . . .
H8A H 0.482289 -0.077499 0.714662 0.113 Uiso 1 1 calc R U . . .
H8B H 0.420045 -0.004611 0.697091 0.113 Uiso 1 1 calc R U . . .
H8C H 0.413338 -0.085085 0.630411 0.113 Uiso 1 1 calc R U . . .
C9 C 0.3825(3) 0.2697(3) 0.7128(4) 0.0242(13) Uani 1 1 d . . . . .
C10 C 0.3779(3) 0.2408(4) 0.8121(4) 0.0381(15) Uani 1 1 d . . . . .
H10 H 0.365652 0.185486 0.823992 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3912(3) 0.2935(4) 0.8948(4) 0.0469(17) Uani 1 1 d . . . . .
H11 H 0.389291 0.272959 0.961628 0.056 Uiso 1 1 calc R U . . .
C12 C 0.4072(3) 0.3750(5) 0.8783(5) 0.0501(18) Uani 1 1 d . . . . .
H12 H 0.416055 0.410199 0.933858 0.060 Uiso 1 1 calc R U . . .
C13 C 0.4101(3) 0.4051(4) 0.7801(5) 0.0441(16) Uani 1 1 d . . . . .
H13 H 0.420599 0.460919 0.768846 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3974(3) 0.3530(3) 0.6974(5) 0.0349(14) Uani 1 1 d . . . . .
H14 H 0.398933 0.374070 0.630826 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3159(3) 0.0502(3) 0.4057(4) 0.0245(13) Uani 1 1 d . . . . .
C16 C 0.2698(3) -0.0091(3) 0.4558(4) 0.0323(14) Uani 1 1 d . . . . .
H16 H 0.267776 -0.009800 0.527317 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2266(3) -0.0676(3) 0.4001(4) 0.0352(15) Uani 1 1 d . . . . .
H17 H 0.195486 -0.106941 0.435041 0.042 Uiso 1 1 calc R U . . .
C18 C 0.2284(3) -0.0690(3) 0.2933(4) 0.0264(13) Uani 1 1 d . . . . .
C19 C 0.2776(3) -0.0110(3) 0.2450(4) 0.0257(13) Uani 1 1 d . . . . .
H19 H 0.281607 -0.011423 0.173542 0.031 Uiso 1 1 calc R U . . .
C20 C 0.3212(3) 0.0481(3) 0.3004(4) 0.0260(13) Uani 1 1 d . . . . .
H20 H 0.354187 0.086250 0.266045 0.031 Uiso 1 1 calc R U . . .
C21 C 0.1726(3) -0.1281(3) 0.2349(4) 0.0327(14) Uani 1 1 d . . . . .
C22 C 0.1755(5) -0.2137(4) 0.2823(5) 0.076(2) Uani 1 1 d . . . . .
H22A H 0.139882 -0.250053 0.244419 0.115 Uiso 1 1 calc R U . . .
H22B H 0.231099 -0.234285 0.280014 0.115 Uiso 1 1 calc R U . . .
H22C H 0.157345 -0.210838 0.352614 0.115 Uiso 1 1 calc R U . . .
C23 C 0.1659(3) 0.2566(3) 0.5572(4) 0.0360(14) Uani 1 1 d . . . . .
H23A H 0.200529 0.268174 0.616481 0.043 Uiso 1 1 calc R U . . .
H23B H 0.162732 0.306581 0.516130 0.043 Uiso 1 1 calc R U . . .
C24 C 0.1968(3) -0.1358(4) 0.1225(4) 0.0450(16) Uani 1 1 d . . . . .
H24A H 0.195486 -0.082308 0.090698 0.067 Uiso 1 1 calc R U . . .
H24B H 0.251645 -0.158238 0.117613 0.067 Uiso 1 1 calc R U . . .
H24C H 0.158724 -0.171919 0.088025 0.067 Uiso 1 1 calc R U . . .
C25 C 0.0842(4) -0.0937(5) 0.2408(6) 0.075(2) Uani 1 1 d . . . . .
H25A H 0.082697 -0.039500 0.210735 0.113 Uiso 1 1 calc R U . . .
H25B H 0.047375 -0.129548 0.203930 0.113 Uiso 1 1 calc R U . . .
H25C H 0.067222 -0.090457 0.311556 0.113 Uiso 1 1 calc R U . . .
B B 0.3014(4) 0.2082(3) 0.4588(5) 0.0244(14) Uani 1 1 d . . . . .
N1 N 0.4377(2) 0.1580(2) 0.5988(3) 0.0232(10) Uani 1 1 d . . . . .
N2 N 0.3515(2) 0.1176(2) 0.4644(3) 0.0207(10) Uani 1 1 d . . . . .
N3 N 0.4636(3) 0.0352(3) 0.5066(4) 0.0348(13) Uani 1 1 d . . . . .
O O 0.34546(19) 0.25826(18) 0.5361(2) 0.0236(8) Uani 1 1 d . . . . .
H1N3 H 0.446(3) 0.004(3) 0.458(4) 0.034(17) 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 O 1.381(5) . ?
C1 N1 1.495(6) . ?
C1 C9 1.505(7) . ?
C1A C2A 1.529(7) . ?
C1A C6A 1.534(6) . ?
C1A B 1.613(8) . ?
C1B C2B 1.534(7) . ?
C1B C23 1.544(7) . ?
C1B B 1.638(7) . ?
C2 N2 1.309(6) . ?
C2 N3 1.356(6) . ?
C2 N1 1.379(6) . ?
C2A C3A 1.523(8) . ?
C2B C3B 1.517(7) . ?
C3 N1 1.505(6) . ?
C3 C4 1.510(7) . ?
C3 C5 1.529(7) . ?
C3A C4A 1.521(8) . ?
C3B C4B 1.524(8) . ?
C4A C5A 1.519(8) . ?
C4B C5B 1.517(8) . ?
C5A C6A 1.524(7) . ?
C5B C23 1.521(7) . ?
C6 N3 1.459(7) . ?
C6 C7 1.504(8) . ?
C6 C8 1.511(8) . ?
C9 C10 1.373(7) . ?
C9 C14 1.385(7) . ?
C10 C11 1.388(8) . ?
C11 C12 1.362(9) . ?
C12 C13 1.367(9) . ?
C13 C14 1.380(8) . ?
C15 C20 1.371(6) . ?
C15 C16 1.379(7) . ?
C15 N2 1.450(6) . ?
C16 C17 1.380(7) . ?
C17 C18 1.388(7) . ?
C18 C19 1.382(7) . ?
C18 C21 1.518(7) . ?
C19 C20 1.389(6) . ?
C21 C22 1.516(8) . ?
C21 C24 1.517(7) . ?
C21 C25 1.538(8) . ?
B O 1.475(6) . ?
B N2 1.676(7) . ?

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
O C1 N1 109.5(4) . . ?
O C1 C9 111.0(4) . . ?
N1 C1 C9 113.0(4) . . ?
C2A C1A C6A 108.6(4) . . ?
C2A C1A B 114.0(4) . . ?
C6A C1A B 111.4(4) . . ?
C2B C1B C23 108.0(4) . . ?
C2B C1B B 115.6(4) . . ?
C23 C1B B 113.1(4) . . ?
N2 C2 N3 120.9(5) . . ?
N2 C2 N1 120.0(4) . . ?
N3 C2 N1 119.1(5) . . ?
C3A C2A C1A 112.3(5) . . ?
C3B C2B C1B 113.3(4) . . ?
N1 C3 C4 115.7(4) . . ?
N1 C3 C5 111.3(4) . . ?
C4 C3 C5 111.8(4) . . ?
C4A C3A C2A 111.3(5) . . ?
C2B C3B C4B 110.7(5) . . ?
C3A C4A C5A 110.4(5) . . ?
C5B C4B C3B 110.3(5) . . ?
C4A C5A C6A 111.2(5) . . ?
C4B C5B C23 111.6(5) . . ?
N3 C6 C7 107.5(5) . . ?
N3 C6 C8 111.6(5) . . ?
C7 C6 C8 112.0(5) . . ?
C5A C6A C1A 113.2(4) . . ?
C10 C9 C14 118.5(5) . . ?
C10 C9 C1 121.0(5) . . ?
C14 C9 C1 120.5(5) . . ?
C9 C10 C11 120.6(6) . . ?
C12 C11 C10 120.2(6) . . ?
C11 C12 C13 119.9(6) . . ?
C12 C13 C14 120.2(6) . . ?
C13 C14 C9 120.6(6) . . ?
C20 C15 C16 119.2(5) . . ?
C20 C15 N2 121.2(5) . . ?
C16 C15 N2 119.4(5) . . ?
C15 C16 C17 120.3(5) . . ?
C16 C17 C18 121.6(5) . . ?
C19 C18 C17 117.1(5) . . ?
C19 C18 C21 123.0(4) . . ?
C17 C18 C21 119.8(5) . . ?
C18 C19 C20 121.6(5) . . ?
C15 C20 C19 120.1(5) . . ?
C22 C21 C18 110.8(5) . . ?
C22 C21 C24 107.9(5) . . ?
C18 C21 C24 112.3(4) . . ?
C22 C21 C25 109.8(5) . . ?
C18 C21 C25 107.5(4) . . ?
C24 C21 C25 108.6(5) . . ?
C5B C23 C1B 112.2(5) . . ?
O B C1A 107.6(4) . . ?
O B C1B 112.7(4) . . ?
C1A B C1B 118.1(4) . . ?
O B N2 102.5(4) . . ?
C1A B N2 109.5(4) . . ?
C1B B N2 105.3(4) . . ?
C2 N1 C1 110.1(4) . . ?
C2 N1 C3 120.6(4) . . ?
C1 N1 C3 114.8(3) . . ?
C2 N2 C15 119.1(4) . . ?
C2 N2 B 124.5(4) . . ?
C15 N2 B 116.2(4) . . ?
C2 N3 C6 126.5(5) . . ?
C1 O B 112.6(4) . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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 1554013'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H49 B2 N3'
_chemical_formula_weight         473.34

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                   9.858(3)
_cell_length_b                   10.828(3)
_cell_length_c                   14.100(4)
_cell_angle_alpha                89.37
_cell_angle_beta                 71.462(5)
_cell_angle_gamma                81.03
_cell_volume                     1408.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7409
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      23.27

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_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            30947
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.906
_diffrn_reflns_theta_max         28.765
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7136
_reflns_number_gt                4601
_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    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury 3.8'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0560P)²+0.5205P] 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         7136
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.006
_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 0.51071(19) 0.47632(16) 0.15996(13) 0.0272(4) Uani 1 1 d . . . . .
H1 H 0.507851 0.412187 0.112437 0.033 Uiso 1 1 calc R U . . .
C2 C 0.4919(2) 0.60472(19) 0.11457(15) 0.0374(5) Uani 1 1 d . . . . .
H2A H 0.408622 0.612010 0.091124 0.045 Uiso 1 1 calc R U . . .
H2B H 0.576567 0.608885 0.056805 0.045 Uiso 1 1 calc R U . . .
C3 C 0.4710(2) 0.71645(17) 0.18635(16) 0.0382(5) Uani 1 1 d . . . . .
H3A H 0.564650 0.725606 0.191770 0.046 Uiso 1 1 calc R U . . .
H3B H 0.436116 0.791642 0.157515 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3659(2) 0.70690(16) 0.29161(16) 0.0348(5) Uani 1 1 d . . . . .
H4A H 0.267610 0.726947 0.289420 0.042 Uiso 1 1 calc R U . . .
H4B H 0.378785 0.769272 0.335505 0.042 Uiso 1 1 calc R U . . .
C5 C 0.38399(19) 0.57769(15) 0.33727(13) 0.0252(4) Uani 1 1 d . . . . .
H5 H 0.303573 0.576161 0.399517 0.030 Uiso 1 1 calc R U . . .
C6 C 0.5287(2) 0.54626(18) 0.35970(15) 0.0370(5) Uani 1 1 d . . . . .
H6A H 0.536511 0.614791 0.400377 0.044 Uiso 1 1 calc R U . . .
H6B H 0.525033 0.472472 0.399501 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6662(2) 0.52251(19) 0.26879(18) 0.0406(5) Uani 1 1 d . . . . .
H7A H 0.691445 0.602583 0.244022 0.049 Uiso 1 1 calc R U . . .
H7B H 0.744856 0.479940 0.290350 0.049 Uiso 1 1 calc R U . . .
C8 C 0.6547(2) 0.44517(18) 0.18282(16) 0.0368(5) Uani 1 1 d . . . . .
H8A H 0.668398 0.357466 0.198154 0.044 Uiso 1 1 calc R U . . .
H8B H 0.733166 0.456686 0.122861 0.044 Uiso 1 1 calc R U . . .
C9 C 0.24991(17) 0.33488(14) 0.27972(11) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.46473(17) 0.21937(14) 0.31073(12) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.5084(2) 0.20304(16) 0.39509(13) 0.0264(4) Uani 1 1 d . . . . .
H11 H 0.478712 0.265958 0.445146 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5956(2) 0.09397(16) 0.40525(14) 0.0300(4) Uani 1 1 d . . . . .
H12 H 0.624169 0.084875 0.462103 0.036 Uiso 1 1 calc R U . . .
C13 C 0.64127(19) -0.00207(15) 0.33250(14) 0.0265(4) Uani 1 1 d . . . . .
C14 C 0.59799(19) 0.01587(16) 0.24823(14) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.627037 -0.047256 0.198374 0.033 Uiso 1 1 calc R U . . .
C15 C 0.51273(19) 0.12528(15) 0.23655(13) 0.0240(4) Uani 1 1 d . . . . .
H15 H 0.487466 0.135731 0.178451 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7364(2) -0.12143(17) 0.34277(17) 0.0400(5) Uani 1 1 d . . . . .
H16A H 0.698241 -0.191942 0.326899 0.060 Uiso 1 1 d R U . . .
H16B H 0.738364 -0.125814 0.410373 0.060 Uiso 1 1 d R U . . .
H16C H 0.833077 -0.122524 0.297846 0.060 Uiso 1 1 d R U . . .
C17 C 0.08571(19) 0.51430(15) 0.24868(15) 0.0275(4) Uani 1 1 d . . . . .
H17 H 0.029131 0.450315 0.241367 0.033 Uiso 1 1 calc R U . . .
C18 C 0.0038(2) 0.58606(18) 0.34762(17) 0.0399(5) Uani 1 1 d . . . . .
H18A H -0.001219 0.530295 0.401592 0.060 Uiso 1 1 d R U . . .
H18B H -0.092586 0.620016 0.348410 0.060 Uiso 1 1 d R U . . .
H18C H 0.053383 0.652919 0.355396 0.060 Uiso 1 1 d R U . . .
C19 C 0.0993(2) 0.59821(18) 0.16025(17) 0.0415(5) Uani 1 1 d . . . . .
H19A H 0.150174 0.664563 0.167028 0.062 Uiso 1 1 d R U . . .
H19B H 0.004431 0.633138 0.158476 0.062 Uiso 1 1 d R U . . .
H19C H 0.151987 0.550021 0.099339 0.062 Uiso 1 1 d R U . . .
C20 C 0.1049(2) 0.20247(16) 0.39589(13) 0.0272(4) Uani 1 1 d . . . . .
H20 H 0.142977 0.251713 0.436569 0.033 Uiso 1 1 calc R U . . .
C21 C -0.0596(2) 0.23654(19) 0.43509(15) 0.0388(5) Uani 1 1 d . . . . .
H21A H -0.087030 0.324052 0.426915 0.058 Uiso 1 1 d R U . . .
H21B H -0.094022 0.218789 0.504768 0.058 Uiso 1 1 d R U . . .
H21C H -0.101443 0.188320 0.398271 0.058 Uiso 1 1 d R U . . .
C22 C 0.1584(2) 0.06549(18) 0.40776(15) 0.0371(5) Uani 1 1 d . . . . .
H22A H 0.118610 0.013726 0.372083 0.056 Uiso 1 1 d R U . . .
H22B H 0.127901 0.047309 0.477466 0.056 Uiso 1 1 d R U . . .
H22C H 0.262351 0.048942 0.381374 0.056 Uiso 1 1 d R U . . .
C23 C 0.2235(2) 0.22023(18) 0.09405(13) 0.0306(4) Uani 1 1 d . . . . .
H23 H 0.285314 0.282620 0.094697 0.037 Uiso 1 1 calc R U . . .
C24 C 0.1092(3) 0.27494(19) 0.04470(16) 0.0435(6) Uani 1 1 d . . . . .
H24A H 0.064388 0.357600 0.074661 0.052 Uiso 1 1 calc R U . . .
H24B H 0.158197 0.284658 -0.025801 0.052 Uiso 1 1 calc R U . . .
C25 C -0.0100(2) 0.19631(18) 0.05413(15) 0.0340(5) Uani 1 1 d . . . . .
H25A H -0.089388 0.247229 0.038223 0.041 Uiso 1 1 calc R U . . .
H25B H 0.027896 0.126888 0.005174 0.041 Uiso 1 1 calc R U . . .
C26 C -0.0685(2) 0.1449(2) 0.15727(15) 0.0365(5) Uani 1 1 d . . . . .
H26A H -0.126707 0.082141 0.152616 0.044 Uiso 1 1 calc R U . . .
H26B H -0.132499 0.212332 0.201853 0.044 Uiso 1 1 calc R U . . .
C27 C 0.04543(18) 0.08587(15) 0.20534(13) 0.0216(4) Uani 1 1 d . . . . .
H27 H -0.003840 0.066679 0.274694 0.026 Uiso 1 1 calc R U . . .
C28 C 0.1418(2) -0.03355(17) 0.14899(15) 0.0364(5) Uani 1 1 d . . . . .
H28A H 0.199159 -0.071767 0.189307 0.044 Uiso 1 1 calc R U . . .
H28B H 0.079453 -0.091943 0.142816 0.044 Uiso 1 1 calc R U . . .
C29 C 0.2441(2) -0.01556(19) 0.04504(15) 0.0374(5) Uani 1 1 d . . . . .
H29A H 0.317117 -0.089786 0.024309 0.045 Uiso 1 1 calc R U . . .
H29B H 0.189520 -0.007083 -0.001724 0.045 Uiso 1 1 calc R U . . .
C30 C 0.3194(2) 0.0983(2) 0.03934(15) 0.0433(6) Uani 1 1 d . . . . .
H30A H 0.361991 0.115216 -0.030672 0.052 Uiso 1 1 calc R U . . .
H30B H 0.398294 0.076937 0.066806 0.052 Uiso 1 1 calc R U . . .
B1 B 0.3812(2) 0.47152(16) 0.26084(14) 0.0181(4) Uani 1 1 d . . . . .
B2 B 0.1443(2) 0.18715(16) 0.20470(14) 0.0186(4) Uani 1 1 d . . . . .
N1 N 0.22753(15) 0.44933(12) 0.24882(11) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.37182(14) 0.33053(11) 0.30282(10) 0.0193(3) Uani 1 1 d . . . . .
N3 N 0.16364(14) 0.24077(11) 0.28975(10) 0.0170(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 C2 1.534(3) . ?
C1 C8 1.540(3) . ?
C1 B1 1.587(3) . ?
C2 C3 1.532(3) . ?
C3 C4 1.529(3) . ?
C4 C5 1.542(2) . ?
C5 C6 1.544(3) . ?
C5 B1 1.594(2) . ?
C6 C7 1.530(3) . ?
C7 C8 1.524(3) . ?
C9 N1 1.3184(19) . ?
C9 N2 1.335(2) . ?
C9 N3 1.4043(19) . ?
C9 B1 2.075(2) . ?
C10 C15 1.384(2) . ?
C10 C11 1.389(2) . ?
C10 N2 1.421(2) . ?
C11 C12 1.383(2) . ?
C12 C13 1.386(3) . ?
C13 C14 1.387(3) . ?
C13 C16 1.508(2) . ?
C14 C15 1.382(2) . ?
C17 N1 1.464(2) . ?
C17 C19 1.518(3) . ?
C17 C18 1.521(3) . ?
C20 N3 1.502(2) . ?
C20 C22 1.521(3) . ?
C20 C21 1.523(3) . ?
C23 C24 1.545(3) . ?
C23 C30 1.550(3) . ?
C23 B2 1.572(3) . ?
C24 C25 1.527(3) . ?
C25 C26 1.519(3) . ?
C26 C27 1.543(2) . ?
C27 C28 1.538(2) . ?
C27 B2 1.575(2) . ?
C28 C29 1.523(3) . ?
C29 C30 1.524(3) . ?
B1 N1 1.631(2) . ?
B1 N2 1.637(2) . ?
B2 N3 1.416(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
C2 C1 C8 112.97(15) . . ?
C2 C1 B1 109.76(15) . . ?
C8 C1 B1 108.47(15) . . ?
C1 C2 C3 114.70(16) . . ?
C4 C3 C2 114.89(15) . . ?
C3 C4 C5 114.75(16) . . ?
C4 C5 C6 112.61(15) . . ?
C4 C5 B1 109.63(14) . . ?
C6 C5 B1 107.36(14) . . ?
C7 C6 C5 116.28(16) . . ?
C8 C7 C6 114.88(16) . . ?
C7 C8 C1 115.39(16) . . ?
N1 C9 N2 103.67(13) . . ?
N1 C9 N3 128.46(14) . . ?
N2 C9 N3 127.83(14) . . ?
N1 C9 B1 51.80(9) . . ?
N2 C9 B1 52.03(9) . . ?
N3 C9 B1 178.31(13) . . ?
C15 C10 C11 118.52(15) . . ?
C15 C10 N2 121.71(14) . . ?
C11 C10 N2 119.76(15) . . ?
C12 C11 C10 120.51(16) . . ?
C11 C12 C13 121.38(17) . . ?
C14 C13 C12 117.53(16) . . ?
C14 C13 C16 120.63(17) . . ?
C12 C13 C16 121.84(17) . . ?
C15 C14 C13 121.59(17) . . ?
C14 C15 C10 120.43(16) . . ?
N1 C17 C19 111.53(16) . . ?
N1 C17 C18 111.23(15) . . ?
C19 C17 C18 111.78(16) . . ?
N3 C20 C22 111.97(15) . . ?
N3 C20 C21 110.87(15) . . ?
C22 C20 C21 113.05(15) . . ?
C24 C23 C30 112.59(16) . . ?
C24 C23 B2 109.28(16) . . ?
C30 C23 B2 107.17(15) . . ?
C25 C24 C23 114.74(15) . . ?
C26 C25 C24 113.96(16) . . ?
C25 C26 C27 116.19(15) . . ?
C28 C27 C26 113.59(15) . . ?
C28 C27 B2 108.73(15) . . ?
C26 C27 B2 106.71(14) . . ?
C29 C28 C27 115.76(15) . . ?
C30 C29 C28 113.67(16) . . ?
C29 C30 C23 116.37(16) . . ?
C1 B1 C5 108.48(14) . . ?
C1 B1 N1 116.26(14) . . ?
C5 B1 N1 119.97(14) . . ?
C1 B1 N2 113.55(13) . . ?
C5 B1 N2 116.90(14) . . ?
N1 B1 N2 79.37(10) . . ?
C1 B1 C9 121.00(13) . . ?
C5 B1 C9 130.40(13) . . ?
N1 B1 C9 39.44(7) . . ?
N2 B1 C9 40.03(7) . . ?
N3 B2 C23 123.70(14) . . ?
N3 B2 C27 126.21(15) . . ?
C23 B2 C27 110.09(14) . . ?
C9 N1 C17 123.91(14) . . ?
C9 N1 B1 88.76(11) . . ?
C17 N1 B1 143.13(13) . . ?
C9 N2 C10 125.23(13) . . ?
C9 N2 B1 87.94(11) . . ?
C10 N2 B1 139.85(13) . . ?
C9 N3 B2 120.82(13) . . ?
C9 N3 C20 113.04(12) . . ?
B2 N3 C20 126.06(13) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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 1554014'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H50 B N4'
_chemical_formula_weight         477.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   9.452(2)
_cell_length_b                   29.608(3)
_cell_length_c                   10.930(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.215(4)
_cell_angle_gamma                90
_cell_volume                     2831.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6771
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.65

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_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  0.347
_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            24390
_diffrn_reflns_av_unetI/netI     0.1254
_diffrn_reflns_av_R_equivalents  0.1313
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         28.744
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7199
_reflns_number_gt                5115
_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    'Mercury 3.8'
_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)+(0.1513P)²+1.5817P] 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         7199
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.1079
_refine_ls_wR_factor_ref         0.2840
_refine_ls_wR_factor_gt          0.2586
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0255(3) 0.12439(8) 0.0970(2) 0.0090(5) Uani 1 1 d . . . . .
C2 C 0.0954(3) 0.10709(8) -0.0459(3) 0.0102(5) Uani 1 1 d . . . . .
C3 C 0.1910(3) 0.18752(9) 0.1983(3) 0.0121(5) Uani 1 1 d . . . . .
C4 C 0.1338(3) 0.21462(9) 0.0683(3) 0.0123(5) Uani 1 1 d . . . . .
H4A H 0.1863 0.2039 0.0129 0.015 Uiso 1 1 calc R U . . .
H4B H 0.0256 0.2088 0.0219 0.015 Uiso 1 1 calc R U . . .
C5 C 0.1580(3) 0.26567(9) 0.0870(3) 0.0177(6) Uani 1 1 d . . . . .
H5A H 0.0937 0.2775 0.1308 0.021 Uiso 1 1 calc R U . . .
H5B H 0.1280 0.2801 0.0013 0.021 Uiso 1 1 calc R U . . .
C6 C 0.3255(3) 0.27683(10) 0.1695(3) 0.0193(6) Uani 1 1 d . . . . .
H6A H 0.3885 0.2686 0.1206 0.023 Uiso 1 1 calc R U . . .
H6B H 0.3363 0.3091 0.1863 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3794(3) 0.25154(9) 0.2997(3) 0.0178(6) Uani 1 1 d . . . . .
H7A H 0.3213 0.2616 0.3513 0.021 Uiso 1 1 calc R U . . .
H7B H 0.4862 0.2584 0.3494 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3599(3) 0.20039(9) 0.2779(3) 0.0149(5) Uani 1 1 d . . . . .
H8A H 0.3950 0.1852 0.3628 0.018 Uiso 1 1 calc R U . . .
H8B H 0.4225 0.1901 0.2305 0.018 Uiso 1 1 calc R U . . .
C9 C 0.2449(3) 0.10204(8) 0.3081(2) 0.0101(5) Uani 1 1 d . . . . .
H9 H 0.3543 0.1047 0.3259 0.012 Uiso 1 1 calc R U . . .
C10 C 0.2276(3) 0.11705(9) 0.4366(3) 0.0137(5) Uani 1 1 d . . . . .
H10A H 0.2512 0.1490 0.4513 0.016 Uiso 1 1 calc R U . . .
H10B H 0.1227 0.1126 0.4285 0.016 Uiso 1 1 calc R U . . .
C11 C 0.3345(3) 0.08997(10) 0.5540(3) 0.0156(6) Uani 1 1 d . . . . .
H11A H 0.3212 0.0996 0.6338 0.019 Uiso 1 1 calc R U . . .
H11B H 0.4395 0.0959 0.5651 0.019 Uiso 1 1 calc R U . . .
C12 C 0.3027(3) 0.03909(10) 0.5342(3) 0.0180(6) Uani 1 1 d . . . . .
H12A H 0.3764 0.0227 0.6075 0.022 Uiso 1 1 calc R U . . .
H12B H 0.2015 0.0326 0.5328 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3131(3) 0.02337(9) 0.4047(3) 0.0172(6) Uani 1 1 d . . . . .
H13A H 0.2837 -0.0082 0.3900 0.021 Uiso 1 1 calc R U . . .
H13B H 0.4181 0.0259 0.4112 0.021 Uiso 1 1 calc R U . . .
C14 C 0.2095(3) 0.05145(9) 0.2873(3) 0.0148(5) Uani 1 1 d . . . . .
H14A H 0.1037 0.0463 0.2750 0.018 Uiso 1 1 calc R U . . .
H14B H 0.2231 0.0417 0.2077 0.018 Uiso 1 1 calc R U . . .
C15 C -0.1701(3) 0.14098(9) 0.2323(2) 0.0103(5) Uani 1 1 d . . . . .
C16 C -0.1948(3) 0.18720(10) 0.2546(3) 0.0157(6) Uani 1 1 d . . . . .
C17 C -0.2316(3) 0.19821(12) 0.3633(3) 0.0225(7) Uani 1 1 d . . . . .
H17 H -0.2431 0.2284 0.3808 0.027 Uiso 1 1 calc R U . . .
C18 C -0.2513(3) 0.16571(13) 0.4451(3) 0.0268(7) Uani 1 1 d . . . . .
H18 H -0.2747 0.1738 0.5175 0.032 Uiso 1 1 calc R U . . .
C19 C -0.2358(3) 0.12052(12) 0.4180(3) 0.0230(7) Uani 1 1 d . . . . .
H19 H -0.2527 0.0984 0.4713 0.028 Uiso 1 1 calc R U . . .
C20 C -0.1956(3) 0.10759(10) 0.3131(3) 0.0154(6) Uani 1 1 d . . . . .
C21 C -0.1849(3) 0.05812(10) 0.2865(3) 0.0214(6) Uani 1 1 d . . . . .
H21A H -0.0911 0.0462 0.3492 0.032 Uiso 1 1 calc R U . . .
H21B H -0.1871 0.0542 0.1987 0.032 Uiso 1 1 calc R U . . .
H21C H -0.2697 0.0425 0.2948 0.032 Uiso 1 1 calc R U . . .
C22 C -0.1918(4) 0.22370(10) 0.1608(3) 0.0215(6) Uani 1 1 d . . . . .
H22A H -0.2699 0.2455 0.1530 0.032 Uiso 1 1 calc R U . . .
H22B H -0.2098 0.2108 0.0757 0.032 Uiso 1 1 calc R U . . .
H22C H -0.0937 0.2382 0.1937 0.032 Uiso 1 1 calc R U . . .
C23 C 0.3744(3) 0.10827(9) 0.0758(3) 0.0139(5) Uani 1 1 d . . . . .
H23 H 0.4374 0.1145 0.1686 0.017 Uiso 1 1 calc R U . . .
C24 C 0.4083(4) 0.05954(11) 0.0502(4) 0.0253(7) Uani 1 1 d . . . . .
H24A H 0.3738 0.0395 0.1023 0.038 Uiso 1 1 calc R U . . .
H24B H 0.5163 0.0558 0.0741 0.038 Uiso 1 1 calc R U . . .
H24C H 0.3561 0.0526 -0.0418 0.038 Uiso 1 1 calc R U . . .
C25 C 0.4285(3) 0.14069(10) -0.0054(3) 0.0182(6) Uani 1 1 d . . . . .
H25A H 0.3789 0.1335 -0.0975 0.027 Uiso 1 1 calc R U . . .
H25B H 0.5371 0.1380 0.0204 0.027 Uiso 1 1 calc R U . . .
H25C H 0.4035 0.1711 0.0096 0.027 Uiso 1 1 calc R U . . .
C26 C -0.1907(3) 0.10667(9) -0.1469(3) 0.0129(5) Uani 1 1 d . . . . .
H26 H -0.1662 0.0990 -0.2239 0.015 Uiso 1 1 calc R U . . .
C27 C -0.2796(3) 0.15089(10) -0.1803(3) 0.0170(6) Uani 1 1 d . . . . .
H27A H -0.3132 0.1586 -0.1103 0.025 Uiso 1 1 calc R U . . .
H27B H -0.3667 0.1475 -0.2613 0.025 Uiso 1 1 calc R U . . .
H27C H -0.2148 0.1744 -0.1902 0.025 Uiso 1 1 calc R U . . .
C28 C -0.2849(3) 0.06741(10) -0.1274(3) 0.0174(6) Uani 1 1 d . . . . .
H28A H -0.2244 0.0404 -0.1085 0.026 Uiso 1 1 calc R U . . .
H28B H -0.3740 0.0632 -0.2064 0.026 Uiso 1 1 calc R U . . .
H28C H -0.3154 0.0740 -0.0549 0.026 Uiso 1 1 calc R U . . .
C29 C 0.0618(4) 0.05117(11) -0.2208(3) 0.0242(7) Uani 1 1 d . . . . .
H29A H 0.0744 0.0300 -0.1509 0.036 Uiso 1 1 calc R U . . .
H29B H 0.1225 0.0418 -0.2696 0.036 Uiso 1 1 calc R U . . .
H29C H -0.0438 0.0523 -0.2788 0.036 Uiso 1 1 calc R U . . .
C30 C 0.0778(3) 0.13313(11) -0.2600(3) 0.0191(6) Uani 1 1 d . . . . .
H30A H -0.0308 0.1362 -0.3046 0.029 Uiso 1 1 calc R U . . .
H30B H 0.1230 0.1269 -0.3235 0.029 Uiso 1 1 calc R U . . .
H30C H 0.1194 0.1607 -0.2142 0.029 Uiso 1 1 calc R U . . .
N1 N 0.2121(2) 0.11525(7) 0.0616(2) 0.0102(4) Uani 1 1 d . . . . .
N2 N -0.0430(2) 0.11158(7) -0.0343(2) 0.0101(4) Uani 1 1 d . . . . .
N3 N 0.1111(3) 0.09585(8) -0.1648(2) 0.0131(5) Uani 1 1 d . . . . .
N4 N -0.1512(2) 0.12859(7) 0.1149(2) 0.0102(4) Uani 1 1 d . . . . .
B1 B 0.1599(3) 0.13307(10) 0.1781(3) 0.0093(5) 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 N4 1.281(3) . ?
C1 N2 1.432(3) . ?
C1 B1 1.658(4) . ?
C2 N1 1.295(3) . ?
C2 N2 1.367(3) . ?
C2 N3 1.403(3) . ?
C3 C4 1.541(4) . ?
C3 C8 1.549(4) . ?
C3 B1 1.639(4) . ?
C4 C5 1.531(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.533(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.516(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.533(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.533(4) . ?
C9 C10 1.540(3) . ?
C9 B1 1.627(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.526(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.535(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.528(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.532(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.406(4) . ?
C15 N4 1.409(3) . ?
C15 C16 1.425(4) . ?
C16 C17 1.398(4) . ?
C16 C22 1.497(4) . ?
C17 C18 1.373(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.504(4) . ?
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 N1 1.497(3) . ?
C23 C25 1.521(4) . ?
C23 C24 1.526(4) . ?
C23 H23 0.9800 . ?
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 N2 1.478(3) . ?
C26 C27 1.524(4) . ?
C26 C28 1.527(4) . ?
C26 H26 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 N3 1.458(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 N3 1.467(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
N1 B1 1.618(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
N4 C1 N2 114.6(2) . . ?
N4 C1 B1 139.2(2) . . ?
N2 C1 B1 106.0(2) . . ?
N1 C2 N2 114.5(2) . . ?
N1 C2 N3 122.2(2) . . ?
N2 C2 N3 123.3(2) . . ?
C4 C3 C8 108.5(2) . . ?
C4 C3 B1 113.9(2) . . ?
C8 C3 B1 114.3(2) . . ?
C5 C4 C3 114.1(2) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 111.1(2) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 110.6(2) . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 111.3(2) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C3 111.6(2) . . ?
C7 C8 H8A 109.3 . . ?
C3 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C3 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C14 C9 C10 109.0(2) . . ?
C14 C9 B1 114.5(2) . . ?
C10 C9 B1 116.5(2) . . ?
C14 C9 H9 105.3 . . ?
C10 C9 H9 105.3 . . ?
B1 C9 H9 105.3 . . ?
C11 C10 C9 110.5(2) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 111.4(2) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 110.6(2) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.5(2) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C9 111.8(2) . . ?
C13 C14 H14A 109.3 . . ?
C9 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C9 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C20 C15 N4 120.0(2) . . ?
C20 C15 C16 119.4(2) . . ?
N4 C15 C16 119.4(2) . . ?
C17 C16 C15 118.6(3) . . ?
C17 C16 C22 119.3(3) . . ?
C15 C16 C22 122.0(2) . . ?
C18 C17 C16 121.9(3) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C20 121.6(3) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C15 119.3(3) . . ?
C19 C20 C21 119.1(3) . . ?
C15 C20 C21 121.6(2) . . ?
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 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C25 114.2(2) . . ?
N1 C23 C24 112.9(2) . . ?
C25 C23 C24 110.5(2) . . ?
N1 C23 H23 106.2 . . ?
C25 C23 H23 106.2 . . ?
C24 C23 H23 106.2 . . ?
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 . . ?
N2 C26 C27 112.1(2) . . ?
N2 C26 C28 112.1(2) . . ?
C27 C26 C28 112.9(2) . . ?
N2 C26 H26 106.4 . . ?
C27 C26 H26 106.4 . . ?
C28 C26 H26 106.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C2 N1 C23 123.8(2) . . ?
C2 N1 B1 111.5(2) . . ?
C23 N1 B1 124.7(2) . . ?
C2 N2 C1 111.5(2) . . ?
C2 N2 C26 123.3(2) . . ?
C1 N2 C26 125.1(2) . . ?
C2 N3 C29 118.4(2) . . ?
C2 N3 C30 114.1(2) . . ?
C29 N3 C30 115.8(2) . . ?
C1 N4 C15 127.5(2) . . ?
N1 B1 C9 107.8(2) . . ?
N1 B1 C3 109.5(2) . . ?
C9 B1 C3 115.7(2) . . ?
N1 B1 C1 95.98(18) . . ?
C9 B1 C1 116.9(2) . . ?
C3 B1 C1 108.9(2) . . ?

_refine_diff_density_max         1.065
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.138

_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_Compound10
_database_code_depnum_ccdc_archive 'CCDC 1554010'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_audit_creation_date             2017-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C49 H78 B2 N4 O'
_chemical_formula_sum            'C55 H92 B2 N4 O'
_chemical_formula_weight         846.94
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4481(18)
_cell_length_b                   14.078(2)
_cell_length_c                   16.683(2)
_cell_angle_alpha                69.089(3)
_cell_angle_beta                 85.835(3)
_cell_angle_gamma                75.449(4)
_cell_volume                     2430.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.73
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0758 before and 0.0648 after correction. The Ratio of minimum to maximum transmission is 0.9138. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21112
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        21.003
_diffrn_reflns_theta_max         21.003
_diffrn_reflns_theta_min         2.235
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3342
_reflns_number_total             5162
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         5162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.5111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1629
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C38(H38A,H38B,
 H38C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C49(H49A,
 H49B,H49C)
2.b Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C25(H25), C31(H31), C37(H37), C40(H40)
2.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,
 H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B),
  C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B)
2.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C20(H20), C44(H44), C45(H45), C47(H47), C48(H48)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.3113(4) 0.5892(3) 0.7788(3) 0.0211(10) Uani 1 1 d . . . . .
C2 C 0.3663(4) 0.4077(3) 0.8248(3) 0.0219(11) Uani 1 1 d . . . . .
C3 C 0.3280(4) 0.4111(3) 0.6655(2) 0.0229(11) Uani 1 1 d . . . . .
H3 H 0.3545 0.3344 0.6861 0.027 Uiso 1 1 calc R . . . .
C4 C 0.3525(4) 0.4466(3) 0.5684(2) 0.0266(11) Uani 1 1 d . . . . .
H4A H 0.3273 0.5224 0.5437 0.032 Uiso 1 1 calc R . . . .
H4B H 0.4385 0.4258 0.5597 0.032 Uiso 1 1 calc R . . . .
C5 C 0.2859(4) 0.3994(3) 0.5226(3) 0.0334(12) Uani 1 1 d . . . . .
H5A H 0.3168 0.3239 0.5434 0.040 Uiso 1 1 calc R . . . .
H5B H 0.3011 0.4258 0.4616 0.040 Uiso 1 1 calc R . . . .
C6 C 0.1507(4) 0.4254(4) 0.5367(3) 0.0452(14) Uani 1 1 d . . . . .
H6A H 0.1120 0.3900 0.5100 0.054 Uiso 1 1 calc R . . . .
H6B H 0.1178 0.5003 0.5101 0.054 Uiso 1 1 calc R . . . .
C7 C 0.1242(4) 0.3910(4) 0.6327(3) 0.0386(13) Uani 1 1 d . . . . .
H7A H 0.0382 0.4139 0.6403 0.046 Uiso 1 1 calc R . . . .
H7B H 0.1467 0.3151 0.6574 0.046 Uiso 1 1 calc R . . . .
C8 C 0.1912(4) 0.4351(3) 0.6799(3) 0.0291(11) Uani 1 1 d . . . . .
H8A H 0.1766 0.4063 0.7408 0.035 Uiso 1 1 calc R . . . .
H8B H 0.1596 0.5104 0.6612 0.035 Uiso 1 1 calc R . . . .
C9 C 0.5491(4) 0.4269(3) 0.7104(3) 0.0226(11) Uani 1 1 d . . . . .
H9 H 0.5610 0.4808 0.6560 0.027 Uiso 1 1 calc R . . . .
C10 C 0.6179(4) 0.4419(3) 0.7796(3) 0.0311(12) Uani 1 1 d . . . . .
H10A H 0.5840 0.5115 0.7814 0.037 Uiso 1 1 calc R . . . .
H10B H 0.6056 0.3917 0.8352 0.037 Uiso 1 1 calc R . . . .
C11 C 0.7539(4) 0.4281(3) 0.7643(3) 0.0390(13) Uani 1 1 d . . . . .
H11A H 0.7676 0.4833 0.7123 0.047 Uiso 1 1 calc R . . . .
H11B H 0.7926 0.4335 0.8118 0.047 Uiso 1 1 calc R . . . .
C12 C 0.8087(4) 0.3222(3) 0.7559(3) 0.0378(13) Uani 1 1 d . . . . .
H12A H 0.8939 0.3157 0.7438 0.045 Uiso 1 1 calc R . . . .
H12B H 0.8010 0.2671 0.8097 0.045 Uiso 1 1 calc R . . . .
C13 C 0.7466(4) 0.3095(3) 0.6848(3) 0.0333(12) Uani 1 1 d . . . . .
H13A H 0.7823 0.2410 0.6812 0.040 Uiso 1 1 calc R . . . .
H13B H 0.7584 0.3620 0.6305 0.040 Uiso 1 1 calc R . . . .
C14 C 0.6109(4) 0.3209(3) 0.7010(3) 0.0255(11) Uani 1 1 d . . . . .
H14A H 0.5993 0.2647 0.7529 0.031 Uiso 1 1 calc R . . . .
H14B H 0.5731 0.3144 0.6537 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3643(4) 0.6590(3) 0.6305(2) 0.0205(11) Uani 1 1 d . . . . .
C16 C 0.4692(4) 0.6925(3) 0.6127(3) 0.0259(11) Uani 1 1 d . . . . .
H16 H 0.5352 0.6592 0.6502 0.031 Uiso 1 1 calc R . . . .
C17 C 0.4760(4) 0.7765(3) 0.5384(3) 0.0259(11) Uani 1 1 d . . . . .
H17 H 0.5470 0.7994 0.5277 0.031 Uiso 1 1 calc R . . . .
C18 C 0.3811(4) 0.8276(3) 0.4793(2) 0.0193(10) Uani 1 1 d . . . . .
C19 C 0.2788(4) 0.7888(3) 0.4972(3) 0.0262(11) Uani 1 1 d . . . . .
H19 H 0.2140 0.8197 0.4584 0.031 Uiso 1 1 calc R . . . .
C20 C 0.2698(4) 0.7051(3) 0.5716(2) 0.0223(11) Uani 1 1 d . . . . .
H20 H 0.2001 0.6803 0.5816 0.027 Uiso 1 1 calc R . . . .
C21 C 0.3873(4) 0.9261(3) 0.4026(2) 0.0211(10) Uani 1 1 d . . . . .
C22 C 0.5158(4) 0.9196(4) 0.3674(3) 0.0402(13) Uani 1 1 d . . . . .
H22A H 0.5697 0.9154 0.4106 0.060 Uiso 1 1 d GR . . . .
H22B H 0.5162 0.9811 0.3179 0.060 Uiso 1 1 d GR . . . .
H22C H 0.5416 0.8585 0.3515 0.060 Uiso 1 1 d GR . . . .
C23 C 0.3039(4) 0.9462(3) 0.3288(3) 0.0385(13) Uani 1 1 d . . . . .
H23A H 0.3250 0.8880 0.3089 0.058 Uiso 1 1 d GR . . . .
H23B H 0.3119 1.0088 0.2828 0.058 Uiso 1 1 d GR . . . .
H23C H 0.2220 0.9547 0.3478 0.058 Uiso 1 1 d GR . . . .
C24 C 0.3495(4) 1.0196(3) 0.4337(3) 0.0395(13) Uani 1 1 d . . . . .
H24A H 0.2652 1.0307 0.4467 0.059 Uiso 1 1 d GR . . . .
H24B H 0.3639 1.0812 0.3894 0.059 Uiso 1 1 d GR . . . .
H24C H 0.3957 1.0054 0.4842 0.059 Uiso 1 1 d GR . . . .
C25 C 0.0626(4) 0.7168(3) 0.7297(2) 0.0244(11) Uani 1 1 d . . . . .
H25 H 0.1027 0.6493 0.7241 0.029 Uiso 1 1 calc R . . . .
C26 C -0.0177(4) 0.7823(3) 0.6480(3) 0.0263(11) Uani 1 1 d . . . . .
H26A H -0.0609 0.8489 0.6526 0.032 Uiso 1 1 calc R . . . .
H26B H 0.0332 0.7966 0.5982 0.032 Uiso 1 1 calc R . . . .
C27 C -0.1075(4) 0.7254(3) 0.6360(3) 0.0376(13) Uani 1 1 d . . . . .
H27A H -0.0643 0.6610 0.6276 0.045 Uiso 1 1 calc R . . . .
H27B H -0.1569 0.7688 0.5851 0.045 Uiso 1 1 calc R . . . .
C28 C -0.1890(4) 0.6996(4) 0.7139(3) 0.0424(13) Uani 1 1 d . . . . .
H28A H -0.2386 0.7641 0.7188 0.051 Uiso 1 1 calc R . . . .
H28B H -0.2421 0.6596 0.7060 0.051 Uiso 1 1 calc R . . . .
C29 C -0.1144(4) 0.6370(4) 0.7953(3) 0.0402(13) Uani 1 1 d . . . . .
H29A H -0.0714 0.5693 0.7930 0.048 Uiso 1 1 calc R . . . .
H29B H -0.1674 0.6252 0.8442 0.048 Uiso 1 1 calc R . . . .
C30 C -0.0243(4) 0.6944(3) 0.8071(3) 0.0314(12) Uani 1 1 d . . . . .
H30A H 0.0227 0.6523 0.8595 0.038 Uiso 1 1 calc R . . . .
H30B H -0.0677 0.7601 0.8131 0.038 Uiso 1 1 calc R . . . .
C31 C 0.1459(4) 0.8823(3) 0.7416(3) 0.0268(11) Uani 1 1 d . . . . .
H31 H 0.2108 0.8858 0.7749 0.032 Uiso 1 1 calc R . . . .
C32 C 0.0277(4) 0.9351(3) 0.7734(3) 0.0297(12) Uani 1 1 d . . . . .
H32A H 0.0210 0.8983 0.8343 0.036 Uiso 1 1 calc R . . . .
H32B H -0.0395 0.9301 0.7441 0.036 Uiso 1 1 calc R . . . .
C33 C 0.0200(4) 1.0504(3) 0.7576(3) 0.0321(12) Uani 1 1 d . . . . .
H33A H -0.0586 1.0820 0.7748 0.039 Uiso 1 1 calc R . . . .
H33B H 0.0807 1.0550 0.7928 0.039 Uiso 1 1 calc R . . . .
C34 C 0.0388(4) 1.1105(3) 0.6643(3) 0.0363(13) Uani 1 1 d . . . . .
H34A H 0.0379 1.1821 0.6573 0.044 Uiso 1 1 calc R . . . .
H34B H -0.0266 1.1122 0.6296 0.044 Uiso 1 1 calc R . . . .
C35 C 0.1580(4) 1.0599(3) 0.6340(3) 0.0367(12) Uani 1 1 d . . . . .
H35A H 0.2236 1.0632 0.6658 0.044 Uiso 1 1 calc R . . . .
H35B H 0.1671 1.0986 0.5737 0.044 Uiso 1 1 calc R . . . .
C36 C 0.1658(4) 0.9456(3) 0.6462(3) 0.0308(12) Uani 1 1 d . . . . .
H36A H 0.2445 0.9147 0.6287 0.037 Uiso 1 1 calc R . . . .
H36B H 0.1051 0.9424 0.6102 0.037 Uiso 1 1 calc R . . . .
C37 C 0.3731(4) 0.7050(4) 0.8353(3) 0.0372(13) Uani 1 1 d . . . . .
H37 H 0.4313 0.6369 0.8574 0.045 Uiso 1 1 calc R . . . .
C38 C 0.3246(5) 0.7332(4) 0.9134(3) 0.0502(15) Uani 1 1 d . . . . .
H38A H 0.3905 0.7321 0.9464 0.075 Uiso 1 1 d GR . . . .
H38B H 0.2810 0.6833 0.9482 0.075 Uiso 1 1 d GR . . . .
H38C H 0.2715 0.8020 0.8948 0.075 Uiso 1 1 d GR . . . .
C39 C 0.4438(4) 0.7810(4) 0.7785(3) 0.0496(15) Uani 1 1 d . . . . .
H39A H 0.4695 0.7628 0.7287 0.074 Uiso 1 1 d GR . . . .
H39B H 0.5131 0.7772 0.8097 0.074 Uiso 1 1 d GR . . . .
H39C H 0.3935 0.8510 0.7611 0.074 Uiso 1 1 d GR . . . .
C40 C 0.2538(4) 0.4963(3) 0.9300(2) 0.0261(11) Uani 1 1 d . . . . .
H40 H 0.2161 0.5690 0.9247 0.031 Uiso 1 1 calc R . . . .
C41 C 0.1537(4) 0.4389(3) 0.9490(3) 0.0349(12) Uani 1 1 d . . . . .
H41A H 0.1026 0.4628 0.8990 0.052 Uiso 1 1 d GR . . . .
H41B H 0.1068 0.4524 0.9956 0.052 Uiso 1 1 d GR . . . .
H41C H 0.1883 0.3650 0.9646 0.052 Uiso 1 1 d GR . . . .
C42 C 0.3465(4) 0.4530(3) 1.0028(3) 0.0373(13) Uani 1 1 d . . . . .
H42A H 0.3772 0.3791 1.0155 0.056 Uiso 1 1 d GR . . . .
H42B H 0.3093 0.4652 1.0528 0.056 Uiso 1 1 d GR . . . .
H42C H 0.4116 0.4874 0.9860 0.056 Uiso 1 1 d GR . . . .
C43 C 0.4236(4) 0.2225(3) 0.8785(2) 0.0250(11) Uani 1 1 d . . . . .
C44 C 0.5362(4) 0.1649(3) 0.9133(3) 0.0316(12) Uani 1 1 d . . . . .
H44 H 0.5808 0.1937 0.9389 0.038 Uiso 1 1 calc R . . . .
C45 C 0.5845(4) 0.0653(3) 0.9109(3) 0.0313(12) Uani 1 1 d . . . . .
H45 H 0.6617 0.0290 0.9330 0.038 Uiso 1 1 calc R . . . .
C46 C 0.5176(4) 0.0196(3) 0.8755(3) 0.0291(12) Uani 1 1 d . . . . .
C47 C 0.4031(4) 0.0742(3) 0.8433(3) 0.0338(12) Uani 1 1 d . . . . .
H47 H 0.3569 0.0435 0.8209 0.041 Uiso 1 1 calc R . . . .
C48 C 0.3559(4) 0.1756(3) 0.8444(2) 0.0305(12) Uani 1 1 d . . . . .
H48 H 0.2788 0.2120 0.8221 0.037 Uiso 1 1 calc R . . . .
C49 C 0.6753(5) -0.1365(3) 0.9020(3) 0.0455(14) Uani 1 1 d . . . . .
H49A H 0.7323 -0.0964 0.8732 0.068 Uiso 1 1 d GR . . . .
H49B H 0.6944 -0.2017 0.8919 0.068 Uiso 1 1 d GR . . . .
H49C H 0.6792 -0.1503 0.9626 0.068 Uiso 1 1 d GR . . . .
B1 B 0.4040(5) 0.4471(4) 0.7238(3) 0.0232(12) Uani 1 1 d . . . . .
B2 B 0.1652(4) 0.7626(4) 0.7530(3) 0.0191(12) Uani 1 1 d . . . . .
N1 N 0.3537(3) 0.5725(2) 0.7087(2) 0.0198(8) Uani 1 1 d . . . . .
N2 N 0.3113(3) 0.4996(3) 0.8467(2) 0.0237(9) Uani 1 1 d . . . . .
N3 N 0.3733(3) 0.3211(3) 0.8877(2) 0.0287(9) Uani 1 1 d . . . . .
N4 N 0.2766(3) 0.6890(2) 0.78773(19) 0.0217(9) Uani 1 1 d . . . . .
O1 O 0.5564(3) -0.0789(2) 0.86994(18) 0.0379(9) 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 1.309(5) . ?
C1 N2 1.362(5) . ?
C1 N4 1.419(5) . ?
C2 B1 1.638(6) . ?
C2 N2 1.448(5) . ?
C2 N3 1.282(5) . ?
C3 C4 1.542(5) . ?
C3 C8 1.537(5) . ?
C3 B1 1.630(6) . ?
C4 C5 1.519(5) . ?
C5 C6 1.520(6) . ?
C6 C7 1.530(6) . ?
C7 C8 1.506(5) . ?
C9 C10 1.546(5) . ?
C9 C14 1.540(5) . ?
C9 B1 1.626(6) . ?
C10 C11 1.534(6) . ?
C11 C12 1.517(6) . ?
C12 C13 1.511(6) . ?
C13 C14 1.535(6) . ?
C15 C16 1.373(6) . ?
C15 C20 1.379(5) . ?
C15 N1 1.455(5) . ?
C16 C17 1.388(6) . ?
C17 C18 1.388(5) . ?
C18 C19 1.383(6) . ?
C18 C21 1.528(5) . ?
C19 C20 1.393(5) . ?
C21 C22 1.537(6) . ?
C21 C23 1.515(5) . ?
C21 C24 1.535(5) . ?
C25 C26 1.553(5) . ?
C25 C30 1.561(6) . ?
C25 B2 1.603(6) . ?
C26 C27 1.517(6) . ?
C27 C28 1.532(6) . ?
C28 C29 1.512(6) . ?
C29 C30 1.521(6) . ?
C31 C32 1.528(5) . ?
C31 C36 1.555(6) . ?
C31 B2 1.586(6) . ?
C32 C33 1.529(5) . ?
C33 C34 1.513(6) . ?
C34 C35 1.515(6) . ?
C35 C36 1.528(6) . ?
C37 C38 1.522(6) . ?
C37 C39 1.515(7) . ?
C37 N4 1.510(5) . ?
C40 C41 1.516(6) . ?
C40 C42 1.519(5) . ?
C40 N2 1.484(5) . ?
C43 C44 1.380(6) . ?
C43 C48 1.397(6) . ?
C43 N3 1.421(5) . ?
C44 C45 1.386(6) . ?
C45 C46 1.390(6) . ?
C46 C47 1.378(6) . ?
C46 O1 1.381(5) . ?
C47 C48 1.399(6) . ?
C49 O1 1.428(5) . ?
B1 N1 1.645(5) . ?
B2 N4 1.432(5) . ?

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 113.4(3) . . ?
N1 C1 N4 124.9(4) . . ?
N2 C1 N4 121.5(3) . . ?
N2 C2 B1 108.0(3) . . ?
N3 C2 B1 138.3(3) . . ?
N3 C2 N2 113.7(3) . . ?
C4 C3 B1 116.8(3) . . ?
C8 C3 C4 109.6(3) . . ?
C8 C3 B1 114.0(3) . . ?
C5 C4 C3 111.8(3) . . ?
C4 C5 C6 112.0(3) . . ?
C5 C6 C7 110.5(4) . . ?
C8 C7 C6 112.4(4) . . ?
C7 C8 C3 113.1(3) . . ?
C10 C9 B1 113.8(3) . . ?
C14 C9 C10 108.9(3) . . ?
C14 C9 B1 115.1(3) . . ?
C11 C10 C9 113.6(3) . . ?
C12 C11 C10 110.3(4) . . ?
C13 C12 C11 110.9(4) . . ?
C12 C13 C14 111.0(3) . . ?
C13 C14 C9 112.1(3) . . ?
C16 C15 C20 119.4(4) . . ?
C16 C15 N1 120.8(4) . . ?
C20 C15 N1 119.7(4) . . ?
C15 C16 C17 119.6(4) . . ?
C18 C17 C16 122.6(4) . . ?
C17 C18 C21 121.1(4) . . ?
C19 C18 C17 116.3(4) . . ?
C19 C18 C21 122.4(4) . . ?
C18 C19 C20 122.0(4) . . ?
C15 C20 C19 120.0(4) . . ?
C18 C21 C22 111.3(3) . . ?
C18 C21 C24 107.4(3) . . ?
C23 C21 C18 113.3(3) . . ?
C23 C21 C22 107.2(3) . . ?
C23 C21 C24 108.1(3) . . ?
C24 C21 C22 109.4(4) . . ?
C26 C25 C30 106.8(3) . . ?
C26 C25 B2 119.3(3) . . ?
C30 C25 B2 108.4(3) . . ?
C27 C26 C25 111.6(3) . . ?
C26 C27 C28 111.3(3) . . ?
C29 C28 C27 110.8(4) . . ?
C28 C29 C30 111.0(4) . . ?
C29 C30 C25 111.7(3) . . ?
C32 C31 C36 110.7(3) . . ?
C32 C31 B2 117.4(4) . . ?
C36 C31 B2 109.1(3) . . ?
C31 C32 C33 112.1(4) . . ?
C34 C33 C32 111.8(3) . . ?
C33 C34 C35 110.8(4) . . ?
C34 C35 C36 111.6(4) . . ?
C35 C36 C31 110.7(3) . . ?
C39 C37 C38 111.6(4) . . ?
N4 C37 C38 112.4(4) . . ?
N4 C37 C39 113.8(4) . . ?
C41 C40 C42 112.3(4) . . ?
N2 C40 C41 112.0(3) . . ?
N2 C40 C42 111.6(3) . . ?
C44 C43 C48 118.1(4) . . ?
C44 C43 N3 119.9(4) . . ?
C48 C43 N3 121.5(4) . . ?
C43 C44 C45 121.5(4) . . ?
C44 C45 C46 120.1(4) . . ?
C47 C46 C45 119.3(4) . . ?
C47 C46 O1 115.6(4) . . ?
O1 C46 C45 125.0(4) . . ?
C46 C47 C48 120.2(4) . . ?
C43 C48 C47 120.6(4) . . ?
C2 B1 N1 94.6(3) . . ?
C3 B1 C2 111.9(4) . . ?
C3 B1 N1 111.3(3) . . ?
C9 B1 C2 113.3(4) . . ?
C9 B1 C3 116.9(3) . . ?
C9 B1 N1 106.5(3) . . ?
C31 B2 C25 122.9(4) . . ?
N4 B2 C25 116.7(3) . . ?
N4 B2 C31 120.4(4) . . ?
C1 N1 C15 121.1(3) . . ?
C1 N1 B1 112.6(3) . . ?
C15 N1 B1 126.0(3) . . ?
C1 N2 C2 111.2(3) . . ?
C1 N2 C40 124.4(3) . . ?
C2 N2 C40 124.3(3) . . ?
C2 N3 C43 121.9(3) . . ?
C1 N4 C37 110.8(3) . . ?
C1 N4 B2 122.4(3) . . ?
B2 N4 C37 126.7(3) . . ?
C46 O1 C49 116.7(3) . . ?

# start Validation Reply Form
_vrf_CHEMW03_Compound10          
;
PROBLEM: The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.90 <> 1.10
RESPONSE: The crystal structure contains a percentage of voids 
occupied by disordered solvent molecules. We have used SQUEEZE 
routine to eliminate one hexane molecule.
;
# end Validation Reply Form

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Compound8a
_database_code_depnum_ccdc_archive 'CCDC 1554015'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H57 B N4 O'
_chemical_formula_weight         584.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   10.6730(7)
_cell_length_b                   11.9049(9)
_cell_length_c                   16.1199(11)
_cell_angle_alpha                68.820(2)
_cell_angle_beta                 85.544(2)
_cell_angle_gamma                64.423(2)
_cell_volume                     1715.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.23

_exptl_crystal_description       prismatic
_exptl_crystal_colour            white-yellowish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'
_exptl_absorpt_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            45028
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_full        25.242
_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             8528
_reflns_number_gt                5921
_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    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Mercury 3.8'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0456P)²+0.7133P] 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         8528
_refine_ls_number_parameters     396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.99849(16) 0.09643(16) 0.25724(11) 0.0119(3) Uani 1 1 d . . . . .
C1 C 0.97976(15) 0.15062(14) 0.14686(10) 0.0124(3) Uani 1 1 d . . . . .
C2 C 1.21628(15) 0.03575(14) 0.18580(10) 0.0126(3) Uani 1 1 d . . . . .
C3 C 0.94135(15) 0.22189(14) 0.29180(9) 0.0125(3) Uani 1 1 d . . . . .
H3 H 0.839609 0.264174 0.279732 0.015 Uiso 1 1 calc R U . . .
C4 C 0.98790(16) 0.33233(15) 0.24090(10) 0.0173(3) Uani 1 1 d . . . . .
H4A H 1.088554 0.295669 0.250615 0.021 Uiso 1 1 calc R U . . .
H4B H 0.963516 0.361993 0.177409 0.021 Uiso 1 1 calc R U . . .
C5 C 0.92052(18) 0.45267(16) 0.27045(11) 0.0226(4) Uani 1 1 d . . . . .
H5A H 0.956326 0.517386 0.238647 0.027 Uiso 1 1 calc R U . . .
H5B H 0.820489 0.495190 0.255152 0.027 Uiso 1 1 calc R U . . .
C6 C 0.95013(18) 0.41098(17) 0.37081(11) 0.0238(4) Uani 1 1 d . . . . .
H6A H 1.049330 0.377275 0.385399 0.029 Uiso 1 1 calc R U . . .
H6B H 0.901471 0.488150 0.388046 0.029 Uiso 1 1 calc R U . . .
C7 C 0.90276(17) 0.30322(16) 0.42253(10) 0.0180(3) Uani 1 1 d . . . . .
H7A H 0.802022 0.340362 0.413099 0.022 Uiso 1 1 calc R U . . .
H7B H 0.927796 0.274069 0.485882 0.022 Uiso 1 1 calc R U . . .
C8 C 0.96947(16) 0.18272(15) 0.39310(10) 0.0165(3) Uani 1 1 d . . . . .
H8A H 0.933150 0.118526 0.425209 0.020 Uiso 1 1 calc R U . . .
H8B H 1.069402 0.139763 0.408853 0.020 Uiso 1 1 calc R U . . .
C9 C 0.94396(15) -0.01852(14) 0.30829(9) 0.0132(3) Uani 1 1 d . . . . .
H9 H 0.999981 -0.072522 0.366071 0.016 Uiso 1 1 calc R U . . .
C10 C 0.97089(16) -0.11534(15) 0.25892(10) 0.0169(3) Uani 1 1 d . . . . .
H10A H 0.921065 -0.064600 0.199814 0.020 Uiso 1 1 calc R U . . .
H10B H 1.069685 -0.155456 0.251532 0.020 Uiso 1 1 calc R U . . .
C11 C 0.92601(18) -0.22664(16) 0.30717(11) 0.0233(4) Uani 1 1 d . . . . .
H11A H 0.940992 -0.280865 0.271379 0.028 Uiso 1 1 calc R U . . .
H11B H 0.982095 -0.283817 0.363886 0.028 Uiso 1 1 calc R U . . .
C12 C 0.77288(19) -0.16711(18) 0.32318(12) 0.0271(4) Uani 1 1 d . . . . .
H12A H 0.746218 -0.238454 0.355689 0.032 Uiso 1 1 calc R U . . .
H12B H 0.716379 -0.115415 0.266300 0.032 Uiso 1 1 calc R U . . .
C13 C 0.74610(18) -0.07716(17) 0.37658(11) 0.0234(4) Uani 1 1 d . . . . .
H13A H 0.797488 -0.130531 0.435102 0.028 Uiso 1 1 calc R U . . .
H13B H 0.647565 -0.038391 0.384934 0.028 Uiso 1 1 calc R U . . .
C14 C 0.79041(16) 0.03501(15) 0.32915(10) 0.0175(3) Uani 1 1 d . . . . .
H14A H 0.776907 0.086659 0.366575 0.021 Uiso 1 1 calc R U . . .
H14B H 0.731230 0.094352 0.273797 0.021 Uiso 1 1 calc R U . . .
C15 C 0.73837(15) 0.25907(15) 0.10246(9) 0.0149(3) Uani 1 1 d . . . . .
C16 C 0.66549(16) 0.18807(16) 0.09741(11) 0.0205(3) Uani 1 1 d . . . . .
H16 H 0.712714 0.109003 0.086642 0.025 Uiso 1 1 calc R U . . .
C17 C 0.52454(17) 0.23316(17) 0.10810(11) 0.0218(3) Uani 1 1 d . . . . .
H17 H 0.478468 0.183253 0.106058 0.026 Uiso 1 1 calc R U . . .
C18 C 0.45153(15) 0.35276(16) 0.12190(10) 0.0188(3) Uani 1 1 d . . . . .
C19 C 0.52105(16) 0.42680(16) 0.12395(10) 0.0185(3) Uani 1 1 d . . . . .
H19 H 0.472461 0.508046 0.131754 0.022 Uiso 1 1 calc R U . . .
C20 C 0.66344(15) 0.37999(15) 0.11437(10) 0.0171(3) Uani 1 1 d . . . . .
H20 H 0.709103 0.430450 0.115959 0.021 Uiso 1 1 calc R U . . .
C21 C 0.23163(17) 0.51806(17) 0.13600(11) 0.0256(4) Uani 1 1 d . . . . .
H21A H 0.267177 0.524376 0.186232 0.038 Uiso 1 1 d R U . . .
H21B H 0.136109 0.532840 0.141968 0.038 Uiso 1 1 d R U . . .
H21C H 0.237225 0.584356 0.081936 0.038 Uiso 1 1 d R U . . .
C22 C 1.14740(16) 0.18225(15) 0.02501(9) 0.0155(3) Uani 1 1 d . . . . .
H22 H 1.249239 0.144919 0.025672 0.019 Uiso 1 1 calc R U . . .
C23 C 1.09624(17) 0.15102(16) -0.04579(10) 0.0202(3) Uani 1 1 d . . . . .
H23A H 1.127139 0.056204 -0.026943 0.030 Uiso 1 1 d R U . . .
H23B H 1.133164 0.182099 -0.101173 0.030 Uiso 1 1 d R U . . .
H23C H 0.996165 0.195160 -0.053961 0.030 Uiso 1 1 d R U . . .
C24 C 1.09524(17) 0.33158(15) 0.00480(10) 0.0198(3) Uani 1 1 d . . . . .
H24A H 0.995876 0.371640 0.006648 0.030 Uiso 1 1 d R U . . .
H24B H 1.118241 0.372960 -0.053562 0.030 Uiso 1 1 d R U . . .
H24C H 1.138785 0.344025 0.048556 0.030 Uiso 1 1 d R U . . .
C25 C 1.40431(16) -0.10756(16) 0.11753(10) 0.0199(3) Uani 1 1 d . . . . .
H25 H 1.374055 -0.049072 0.054763 0.024 Uiso 1 1 calc R U . . .
C26 C 1.3448(2) -0.20865(19) 0.14058(13) 0.0356(5) Uani 1 1 d . . . . .
H26A H 1.378203 -0.270900 0.200679 0.053 Uiso 1 1 d R U . . .
H26B H 1.373654 -0.255945 0.100125 0.053 Uiso 1 1 d R U . . .
H26C H 1.244795 -0.163219 0.135509 0.053 Uiso 1 1 d R U . . .
C27 C 1.56211(19) -0.1725(2) 0.12858(14) 0.0406(5) Uani 1 1 d . . . . .
H27A H 1.594903 -0.104552 0.111961 0.061 Uiso 1 1 d R U . . .
H27B H 1.597327 -0.224166 0.090981 0.061 Uiso 1 1 d R U . . .
H27C H 1.594221 -0.229955 0.189797 0.061 Uiso 1 1 d R U . . .
C28 C 1.26391(14) -0.06793(14) 0.34337(9) 0.0124(3) Uani 1 1 d . . . . .
C29 C 1.32687(15) -0.01843(15) 0.38386(10) 0.0162(3) Uani 1 1 d . . . . .
H29 H 1.306332 0.072000 0.360359 0.019 Uiso 1 1 calc R U . . .
C30 C 1.42055(16) -0.10281(15) 0.45938(10) 0.0171(3) Uani 1 1 d . . . . .
H30 H 1.459338 -0.066843 0.486635 0.021 Uiso 1 1 calc R U . . .
C31 C 1.45812(15) -0.23941(14) 0.49550(9) 0.0135(3) Uani 1 1 d . . . . .
C32 C 1.39434(16) -0.28706(15) 0.45277(10) 0.0181(3) Uani 1 1 d . . . . .
H32 H 1.417179 -0.377974 0.474912 0.022 Uiso 1 1 calc R U . . .
C33 C 1.29819(16) -0.20387(15) 0.37853(10) 0.0168(3) Uani 1 1 d . . . . .
H33 H 1.256725 -0.238950 0.352318 0.020 Uiso 1 1 calc R U . . .
C34 C 1.56509(16) -0.33584(15) 0.57652(10) 0.0164(3) Uani 1 1 d . . . . .
C35 C 1.50486(17) -0.42314(16) 0.64604(10) 0.0219(4) Uani 1 1 d . . . . .
H35A H 1.423732 -0.367154 0.666657 0.033 Uiso 1 1 d R U . . .
H35B H 1.573723 -0.485385 0.695645 0.033 Uiso 1 1 d R U . . .
H35C H 1.479569 -0.471305 0.619114 0.033 Uiso 1 1 d R U . . .
C36 C 1.69797(16) -0.42597(16) 0.54598(11) 0.0223(4) Uani 1 1 d . . . . .
H36A H 1.674570 -0.471768 0.515929 0.033 Uiso 1 1 d R U . . .
H36B H 1.763100 -0.490238 0.597090 0.033 Uiso 1 1 d R U . . .
H36C H 1.739220 -0.372196 0.505876 0.033 Uiso 1 1 d R U . . .
C37 C 1.60556(17) -0.26105(16) 0.62156(11) 0.0223(4) Uani 1 1 d . . . . .
H37A H 1.646685 -0.208622 0.579869 0.033 Uiso 1 1 d R U . . .
H37B H 1.671503 -0.324436 0.672451 0.033 Uiso 1 1 d R U . . .
H37C H 1.523726 -0.203320 0.640581 0.033 Uiso 1 1 d R U . . .
N1 N 1.16826(12) 0.02103(12) 0.26463(8) 0.0119(3) Uani 1 1 d . . . . .
N2 N 1.11643(12) 0.11453(12) 0.11594(8) 0.0128(3) Uani 1 1 d . . . . .
H3N H 1.410274 -0.070487 0.225400 0.015 Uiso 1 1 d R U . . .
N3 N 1.35491(12) -0.02188(12) 0.17287(8) 0.0154(3) Uani 1 1 d . . . . .
N4 N 0.88006(13) 0.21605(12) 0.08444(8) 0.0155(3) Uani 1 1 d . . . . .
O1 O 0.31204(11) 0.38873(12) 0.13287(8) 0.0261(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
B1 N1 1.6294(19) . ?
B1 C3 1.636(2) . ?
B1 C9 1.640(2) . ?
B1 C1 1.654(2) . ?
C1 N4 1.2790(18) . ?
C1 N2 1.4358(18) . ?
C2 N1 1.3129(19) . ?
C2 N2 1.3579(18) . ?
C2 N3 1.3719(19) . ?
C3 C4 1.540(2) . ?
C3 C8 1.542(2) . ?
C4 C5 1.532(2) . ?
C5 C6 1.526(2) . ?
C6 C7 1.523(2) . ?
C7 C8 1.532(2) . ?
C9 C14 1.540(2) . ?
C9 C10 1.545(2) . ?
C10 C11 1.528(2) . ?
C11 C12 1.519(2) . ?
C12 C13 1.527(2) . ?
C13 C14 1.531(2) . ?
C15 C20 1.389(2) . ?
C15 C16 1.398(2) . ?
C15 N4 1.4156(19) . ?
C16 C17 1.382(2) . ?
C17 C18 1.388(2) . ?
C18 O1 1.3764(18) . ?
C18 C19 1.385(2) . ?
C19 C20 1.392(2) . ?
C21 O1 1.421(2) . ?
C22 N2 1.4861(18) . ?
C22 C23 1.522(2) . ?
C22 C24 1.527(2) . ?
C25 N3 1.495(2) . ?
C25 C27 1.513(2) . ?
C25 C26 1.513(2) . ?
C28 C29 1.383(2) . ?
C28 C33 1.390(2) . ?
C28 N1 1.4392(18) . ?
C29 C30 1.389(2) . ?
C30 C31 1.390(2) . ?
C31 C32 1.396(2) . ?
C31 C34 1.531(2) . ?
C32 C33 1.387(2) . ?
C34 C37 1.534(2) . ?
C34 C36 1.538(2) . ?
C34 C35 1.540(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
N1 B1 C3 112.46(11) . . ?
N1 B1 C9 107.17(11) . . ?
C3 B1 C9 115.18(12) . . ?
N1 B1 C1 94.66(11) . . ?
C3 B1 C1 110.76(11) . . ?
C9 B1 C1 114.75(12) . . ?
N4 C1 N2 114.25(13) . . ?
N4 C1 B1 137.88(13) . . ?
N2 C1 B1 107.84(11) . . ?
N1 C2 N2 114.33(13) . . ?
N1 C2 N3 124.12(13) . . ?
N2 C2 N3 121.54(13) . . ?
C4 C3 C8 109.06(12) . . ?
C4 C3 B1 114.90(12) . . ?
C8 C3 B1 115.09(12) . . ?
C5 C4 C3 112.44(12) . . ?
C6 C5 C4 111.46(13) . . ?
C7 C6 C5 110.58(13) . . ?
C6 C7 C8 111.53(13) . . ?
C7 C8 C3 112.61(12) . . ?
C14 C9 C10 109.47(12) . . ?
C14 C9 B1 115.07(12) . . ?
C10 C9 B1 112.77(12) . . ?
C11 C10 C9 113.69(13) . . ?
C12 C11 C10 110.16(14) . . ?
C11 C12 C13 110.45(14) . . ?
C12 C13 C14 111.55(13) . . ?
C13 C14 C9 112.44(13) . . ?
C20 C15 C16 117.92(14) . . ?
C20 C15 N4 121.64(14) . . ?
C16 C15 N4 119.95(14) . . ?
C17 C16 C15 121.23(15) . . ?
C16 C17 C18 120.19(15) . . ?
O1 C18 C19 124.61(15) . . ?
O1 C18 C17 116.04(14) . . ?
C19 C18 C17 119.35(14) . . ?
C18 C19 C20 120.21(15) . . ?
C15 C20 C19 121.03(15) . . ?
N2 C22 C23 111.99(12) . . ?
N2 C22 C24 110.79(12) . . ?
C23 C22 C24 113.88(12) . . ?
N3 C25 C27 107.34(14) . . ?
N3 C25 C26 112.81(13) . . ?
C27 C25 C26 112.55(15) . . ?
C29 C28 C33 118.83(13) . . ?
C29 C28 N1 119.54(13) . . ?
C33 C28 N1 121.60(13) . . ?
C28 C29 C30 120.47(14) . . ?
C29 C30 C31 122.02(14) . . ?
C30 C31 C32 116.35(13) . . ?
C30 C31 C34 123.28(13) . . ?
C32 C31 C34 120.36(13) . . ?
C33 C32 C31 122.45(14) . . ?
C32 C33 C28 119.86(14) . . ?
C31 C34 C37 111.77(12) . . ?
C31 C34 C36 109.20(12) . . ?
C37 C34 C36 108.06(13) . . ?
C31 C34 C35 110.04(12) . . ?
C37 C34 C35 108.28(13) . . ?
C36 C34 C35 109.44(13) . . ?
C2 N1 C28 119.00(12) . . ?
C2 N1 B1 112.07(11) . . ?
C28 N1 B1 128.46(11) . . ?
C2 N2 C1 110.67(12) . . ?
C2 N2 C22 122.53(12) . . ?
C1 N2 C22 124.75(11) . . ?
C2 N3 C25 120.63(12) . . ?
C1 N4 C15 122.09(13) . . ?
C18 O1 C21 116.95(13) . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.056

