# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1435544'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 B2 N4'
_chemical_formula_weight         514.22

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   27.194(4)
_cell_length_b                   10.9496(13)
_cell_length_c                   19.143(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.772(4)
_cell_angle_gamma                90
_cell_volume                     5599.6(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2459
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      21.20

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             2160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9803
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18566
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.524
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6438
_reflns_number_gt                3484
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1243P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0053(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6438
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.2144
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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
N3 N 0.11704(6) 0.93766(15) 0.07413(9) 0.0383(4) Uani 1 1 d . . . . .
N2 N 0.15791(7) 0.85603(15) 0.07904(9) 0.0385(4) Uani 1 1 d . . . . .
N4 N 0.17362(7) 1.11396(16) 0.06679(10) 0.0425(5) Uani 1 1 d . . . . .
N1 N 0.10823(8) 0.69224(16) 0.12362(10) 0.0467(5) Uani 1 1 d . . . . .
C29 C 0.08134(8) 1.16095(19) 0.07751(12) 0.0426(5) Uani 1 1 d . . . . .
C19 C 0.21164(9) 1.0299(2) 0.07548(12) 0.0438(6) Uani 1 1 d . . . . .
C17 C 0.07683(8) 0.8948(2) 0.09407(12) 0.0407(5) Uani 1 1 d . . . . .
H17 H 0.0495 0.9472 0.0900 0.049 Uiso 1 1 calc R U . . .
C18 C 0.20138(8) 0.9064(2) 0.07894(12) 0.0424(5) Uani 1 1 d . . . . .
H18 H 0.2284 0.8536 0.0815 0.051 Uiso 1 1 calc R U . . .
C16 C 0.07100(8) 0.77838(19) 0.12082(12) 0.0411(5) Uani 1 1 d . . . . .
C12 C 0.13498(8) 0.6573(2) 0.00037(12) 0.0444(6) Uani 1 1 d . . . . .
C6 C 0.20205(9) 0.6503(2) 0.12273(12) 0.0453(6) Uani 1 1 d . . . . .
C1 C 0.23437(9) 0.5818(2) 0.08944(14) 0.0510(6) Uani 1 1 d . . . . .
H1 H 0.2253 0.5668 0.0409 0.061 Uiso 1 1 calc R U . . .
C28 C 0.10324(9) 1.0678(2) -0.04420(12) 0.0452(6) Uani 1 1 d . . . . .
C27 C 0.11908(10) 1.1587(2) -0.08661(14) 0.0541(7) Uani 1 1 d . . . . .
H27 H 0.1400 1.2207 -0.0652 0.065 Uiso 1 1 calc R U . . .
C15 C 0.03323(10) 0.7311(2) 0.15357(13) 0.0532(6) Uani 1 1 d . . . . .
H15 H 0.0036 0.7698 0.1586 0.064 Uiso 1 1 calc R U . . .
B2 B 0.11831(10) 1.0752(2) 0.04137(14) 0.0422(6) Uani 1 1 d . . . . .
C14 C 0.04862(11) 0.6161(2) 0.17681(15) 0.0638(7) Uani 1 1 d . . . . .
H14 H 0.0316 0.5626 0.2016 0.077 Uiso 1 1 calc R U . . .
C23 C 0.07274(10) 0.9777(2) -0.08004(14) 0.0576(7) Uani 1 1 d . . . . .
H23 H 0.0616 0.9153 -0.0540 0.069 Uiso 1 1 calc R U . . .
C30 C 0.08974(11) 1.1790(2) 0.15096(14) 0.0594(7) Uani 1 1 d . . . . .
H30 H 0.1172 1.1413 0.1789 0.071 Uiso 1 1 calc R U . . .
C20 C 0.25713(9) 1.0927(2) 0.08646(14) 0.0540(6) Uani 1 1 d . . . . .
H20 H 0.2889 1.0581 0.0932 0.065 Uiso 1 1 calc R U . . .
C2 C 0.27879(11) 0.5357(2) 0.12498(17) 0.0635(8) Uani 1 1 d . . . . .
H2 H 0.2989 0.4901 0.1004 0.076 Uiso 1 1 calc R U . . .
C11 C 0.14984(11) 0.7119(2) -0.05760(14) 0.0599(7) Uani 1 1 d . . . . .
H11 H 0.1674 0.7851 -0.0508 0.072 Uiso 1 1 calc R U . . .
C21 C 0.24618(10) 1.2145(2) 0.08538(15) 0.0603(7) Uani 1 1 d . . . . .
H21 H 0.2692 1.2783 0.0918 0.072 Uiso 1 1 calc R U . . .
C22 C 0.19426(10) 1.2256(2) 0.07282(14) 0.0546(7) Uani 1 1 d . . . . .
H22 H 0.1767 1.2989 0.0692 0.065 Uiso 1 1 calc R U . . .
C7 C 0.10831(10) 0.5482(2) -0.01390(15) 0.0603(7) Uani 1 1 d . . . . .
H7 H 0.0975 0.5081 0.0233 0.072 Uiso 1 1 calc R U . . .
C34 C 0.04137(10) 1.2213(2) 0.03872(16) 0.0586(7) Uani 1 1 d . . . . .
H34 H 0.0350 1.2141 -0.0106 0.070 Uiso 1 1 calc R U . . .
C26 C 0.10397(12) 1.1577(3) -0.16038(15) 0.0688(8) Uani 1 1 d . . . . .
H26 H 0.1145 1.2195 -0.1875 0.083 Uiso 1 1 calc R U . . .
C8 C 0.09738(12) 0.4975(3) -0.08145(19) 0.0759(9) Uani 1 1 d . . . . .
H8 H 0.0792 0.4252 -0.0892 0.091 Uiso 1 1 calc R U . . .
C13 C 0.09384(11) 0.5946(2) 0.15681(15) 0.0637(8) Uani 1 1 d . . . . .
H13 H 0.1119 0.5223 0.1652 0.076 Uiso 1 1 calc R U . . .
B1 B 0.15097(10) 0.7081(2) 0.08049(14) 0.0433(6) Uani 1 1 d . . . . .
C24 C 0.05831(12) 0.9774(3) -0.15297(15) 0.0727(8) Uani 1 1 d . . . . .
H24 H 0.0377 0.9153 -0.1749 0.087 Uiso 1 1 calc R U . . .
C32 C 0.01861(12) 1.3067(3) 0.1436(2) 0.0778(10) Uani 1 1 d . . . . .
H32 H -0.0028 1.3536 0.1653 0.093 Uiso 1 1 calc R U . . .
C5 C 0.21884(12) 0.6709(3) 0.19502(15) 0.0763(9) Uani 1 1 d . . . . .
H5 H 0.1995 0.7185 0.2197 0.092 Uiso 1 1 calc R U . . .
C33 C 0.00999(11) 1.2933(3) 0.0711(2) 0.0746(9) Uani 1 1 d . . . . .
H33 H -0.0171 1.3326 0.0433 0.089 Uiso 1 1 calc R U . . .
C31 C 0.05925(12) 1.2501(3) 0.18357(17) 0.0694(8) Uani 1 1 d . . . . .
H31 H 0.0661 1.2598 0.2327 0.083 Uiso 1 1 calc R U . . .
C25 C 0.07372(12) 1.0663(3) -0.19323(15) 0.0700(8) Uani 1 1 d . . . . .
H25 H 0.0639 1.0653 -0.2424 0.084 Uiso 1 1 calc R U . . .
C9 C 0.11361(13) 0.5546(3) -0.13665(18) 0.0809(10) Uani 1 1 d . . . . .
H9 H 0.1069 0.5204 -0.1819 0.097 Uiso 1 1 calc R U . . .
C3 C 0.29398(12) 0.5557(3) 0.19605(18) 0.0790(9) Uani 1 1 d . . . . .
H3 H 0.3243 0.5249 0.2203 0.095 Uiso 1 1 calc R U . . .
C10 C 0.13960(12) 0.6619(3) -0.12520(15) 0.0749(9) Uani 1 1 d . . . . .
H10 H 0.1504 0.7011 -0.1627 0.090 Uiso 1 1 calc R U . . .
C4 C 0.26296(13) 0.6233(4) 0.23107(17) 0.0910(11) Uani 1 1 d . . . . .
H4 H 0.2722 0.6366 0.2797 0.109 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C17 1.310(3) . ?
N3 N2 1.416(2) . ?
N3 B2 1.635(3) . ?
N2 C18 1.305(3) . ?
N2 B1 1.632(3) . ?
N4 C22 1.341(3) . ?
N4 C19 1.371(3) . ?
N4 B2 1.551(3) . ?
N1 C13 1.339(3) . ?
N1 C16 1.377(3) . ?
N1 B1 1.556(3) . ?
C29 C34 1.367(3) . ?
C29 C30 1.396(3) . ?
C29 B2 1.622(3) . ?
C19 C18 1.385(3) . ?
C19 C20 1.396(3) . ?
C17 C16 1.394(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C16 C15 1.399(3) . ?
C12 C11 1.385(3) . ?
C12 C7 1.398(3) . ?
C12 B1 1.613(4) . ?
C6 C5 1.392(4) . ?
C6 C1 1.397(3) . ?
C6 B1 1.601(4) . ?
C1 C2 1.368(4) . ?
C1 H1 0.9300 . ?
C28 C23 1.385(3) . ?
C28 C27 1.402(3) . ?
C28 B2 1.615(4) . ?
C27 C26 1.395(4) . ?
C27 H27 0.9300 . ?
C15 C14 1.374(4) . ?
C15 H15 0.9300 . ?
C14 C13 1.375(4) . ?
C14 H14 0.9300 . ?
C23 C24 1.378(4) . ?
C23 H23 0.9300 . ?
C30 C31 1.370(4) . ?
C30 H30 0.9300 . ?
C20 C21 1.367(3) . ?
C20 H20 0.9300 . ?
C2 C3 1.364(4) . ?
C2 H2 0.9300 . ?
C11 C10 1.385(4) . ?
C11 H11 0.9300 . ?
C21 C22 1.393(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9300 . ?
C34 C33 1.389(4) . ?
C34 H34 0.9300 . ?
C26 C25 1.371(4) . ?
C26 H26 0.9300 . ?
C8 C9 1.370(5) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C24 C25 1.355(4) . ?
C24 H24 0.9300 . ?
C32 C31 1.369(4) . ?
C32 C33 1.372(5) . ?
C32 H32 0.9300 . ?
C5 C4 1.370(4) . ?
C5 H5 0.9300 . ?
C33 H33 0.9300 . ?
C31 H31 0.9300 . ?
C25 H25 0.9300 . ?
C9 C10 1.367(5) . ?
C9 H9 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?

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
C17 N3 N2 116.25(17) . . ?
C17 N3 B2 121.35(18) . . ?
N2 N3 B2 122.32(16) . . ?
C18 N2 N3 115.68(17) . . ?
C18 N2 B1 121.82(18) . . ?
N3 N2 B1 122.42(17) . . ?
C22 N4 C19 107.92(19) . . ?
C22 N4 B2 129.9(2) . . ?
C19 N4 B2 121.31(18) . . ?
C13 N1 C16 106.7(2) . . ?
C13 N1 B1 130.9(2) . . ?
C16 N1 B1 121.31(18) . . ?
C34 C29 C30 116.3(2) . . ?
C34 C29 B2 122.8(2) . . ?
C30 C29 B2 120.9(2) . . ?
N4 C19 C18 120.5(2) . . ?
N4 C19 C20 108.3(2) . . ?
C18 C19 C20 130.9(2) . . ?
N3 C17 C16 126.4(2) . . ?
N3 C17 H17 116.8 . . ?
C16 C17 H17 116.8 . . ?
N2 C18 C19 127.1(2) . . ?
N2 C18 H18 116.4 . . ?
C19 C18 H18 116.4 . . ?
N1 C16 C17 120.5(2) . . ?
N1 C16 C15 109.0(2) . . ?
C17 C16 C15 130.3(2) . . ?
C11 C12 C7 115.5(2) . . ?
C11 C12 B1 123.1(2) . . ?
C7 C12 B1 121.2(2) . . ?
C5 C6 C1 115.0(2) . . ?
C5 C6 B1 122.0(2) . . ?
C1 C6 B1 122.8(2) . . ?
C2 C1 C6 123.0(2) . . ?
C2 C1 H1 118.5 . . ?
C6 C1 H1 118.5 . . ?
C23 C28 C27 116.0(2) . . ?
C23 C28 B2 123.6(2) . . ?
C27 C28 B2 120.3(2) . . ?
C26 C27 C28 121.1(3) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C14 C15 C16 106.2(2) . . ?
C14 C15 H15 126.9 . . ?
C16 C15 H15 126.9 . . ?
N4 B2 C28 112.30(19) . . ?
N4 B2 C29 110.50(19) . . ?
C28 B2 C29 113.70(19) . . ?
N4 B2 N3 102.73(17) . . ?
C28 B2 N3 108.86(18) . . ?
C29 B2 N3 108.08(18) . . ?
C15 C14 C13 107.5(2) . . ?
C15 C14 H14 126.2 . . ?
C13 C14 H14 126.2 . . ?
C24 C23 C28 122.3(3) . . ?
C24 C23 H23 118.8 . . ?
C28 C23 H23 118.8 . . ?
C31 C30 C29 122.7(3) . . ?
C31 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
C21 C20 C19 107.1(2) . . ?
C21 C20 H20 126.5 . . ?
C19 C20 H20 126.5 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C10 C11 C12 122.7(3) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C20 C21 C22 107.4(2) . . ?
C20 C21 H21 126.3 . . ?
C22 C21 H21 126.3 . . ?
N4 C22 C21 109.3(2) . . ?
N4 C22 H22 125.4 . . ?
C21 C22 H22 125.4 . . ?
C8 C7 C12 122.5(3) . . ?
C8 C7 H7 118.8 . . ?
C12 C7 H7 118.8 . . ?
C29 C34 C33 121.6(3) . . ?
C29 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C25 C26 C27 120.5(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N1 C13 C14 110.6(2) . . ?
N1 C13 H13 124.7 . . ?
C14 C13 H13 124.7 . . ?
N1 B1 C6 110.60(19) . . ?
N1 B1 C12 111.8(2) . . ?
C6 B1 C12 113.49(19) . . ?
N1 B1 N2 102.70(17) . . ?
C6 B1 N2 107.96(19) . . ?
C12 B1 N2 109.70(18) . . ?
C25 C24 C23 121.0(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C31 C32 C33 118.9(3) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C32 C33 C34 120.6(3) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C32 C31 C30 119.8(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C24 C25 C26 119.1(3) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N3 N2 C18 -161.29(19) . . . . ?
B2 N3 N2 C18 22.0(3) . . . . ?
C17 N3 N2 B1 21.8(3) . . . . ?
B2 N3 N2 B1 -154.83(19) . . . . ?
C22 N4 C19 C18 173.5(2) . . . . ?
B2 N4 C19 C18 -16.0(3) . . . . ?
C22 N4 C19 C20 -0.7(3) . . . . ?
B2 N4 C19 C20 169.8(2) . . . . ?
N2 N3 C17 C16 1.5(3) . . . . ?
B2 N3 C17 C16 178.2(2) . . . . ?
N3 N2 C18 C19 0.9(3) . . . . ?
B1 N2 C18 C19 177.8(2) . . . . ?
N4 C19 C18 N2 -4.4(4) . . . . ?
C20 C19 C18 N2 168.3(2) . . . . ?
C13 N1 C16 C17 175.0(2) . . . . ?
B1 N1 C16 C17 -16.0(3) . . . . ?
C13 N1 C16 C15 0.2(3) . . . . ?
B1 N1 C16 C15 169.3(2) . . . . ?
N3 C17 C16 N1 -4.9(4) . . . . ?
N3 C17 C16 C15 168.6(2) . . . . ?
C5 C6 C1 C2 1.3(4) . . . . ?
B1 C6 C1 C2 177.9(2) . . . . ?
C23 C28 C27 C26 0.9(3) . . . . ?
B2 C28 C27 C26 -176.2(2) . . . . ?
N1 C16 C15 C14 0.7(3) . . . . ?
C17 C16 C15 C14 -173.3(3) . . . . ?
C22 N4 B2 C28 82.9(3) . . . . ?
C19 N4 B2 C28 -85.3(2) . . . . ?
C22 N4 B2 C29 -45.2(3) . . . . ?
C19 N4 B2 C29 146.6(2) . . . . ?
C22 N4 B2 N3 -160.3(2) . . . . ?
C19 N4 B2 N3 31.5(3) . . . . ?
C23 C28 B2 N4 140.6(2) . . . . ?
C27 C28 B2 N4 -42.5(3) . . . . ?
C23 C28 B2 C29 -93.0(3) . . . . ?
C27 C28 B2 C29 83.9(3) . . . . ?
C23 C28 B2 N3 27.6(3) . . . . ?
C27 C28 B2 N3 -155.6(2) . . . . ?
C34 C29 B2 N4 127.1(2) . . . . ?
C30 C29 B2 N4 -51.4(3) . . . . ?
C34 C29 B2 C28 -0.3(3) . . . . ?
C30 C29 B2 C28 -178.7(2) . . . . ?
C34 C29 B2 N3 -121.3(2) . . . . ?
C30 C29 B2 N3 60.3(3) . . . . ?
C17 N3 B2 N4 147.80(19) . . . . ?
N2 N3 B2 N4 -35.7(2) . . . . ?
C17 N3 B2 C28 -93.0(2) . . . . ?
N2 N3 B2 C28 83.5(2) . . . . ?
C17 N3 B2 C29 31.0(3) . . . . ?
N2 N3 B2 C29 -152.54(18) . . . . ?
C16 C15 C14 C13 -1.4(3) . . . . ?
C27 C28 C23 C24 -0.5(4) . . . . ?
B2 C28 C23 C24 176.4(2) . . . . ?
C34 C29 C30 C31 1.8(4) . . . . ?
B2 C29 C30 C31 -179.6(2) . . . . ?
N4 C19 C20 C21 0.9(3) . . . . ?
C18 C19 C20 C21 -172.5(3) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C7 C12 C11 C10 -0.6(4) . . . . ?
B1 C12 C11 C10 174.2(2) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C19 N4 C22 C21 0.1(3) . . . . ?
B2 N4 C22 C21 -169.3(2) . . . . ?
C20 C21 C22 N4 0.4(3) . . . . ?
C11 C12 C7 C8 0.1(4) . . . . ?
B1 C12 C7 C8 -174.9(2) . . . . ?
C30 C29 C34 C33 -2.1(4) . . . . ?
B2 C29 C34 C33 179.4(2) . . . . ?
C28 C27 C26 C25 -1.0(4) . . . . ?
C12 C7 C8 C9 0.8(4) . . . . ?
C16 N1 C13 C14 -1.1(3) . . . . ?
B1 N1 C13 C14 -168.8(3) . . . . ?
C15 C14 C13 N1 1.6(3) . . . . ?
C13 N1 B1 C6 -47.1(3) . . . . ?
C16 N1 B1 C6 146.8(2) . . . . ?
C13 N1 B1 C12 80.4(3) . . . . ?
C16 N1 B1 C12 -85.7(3) . . . . ?
C13 N1 B1 N2 -162.1(2) . . . . ?
C16 N1 B1 N2 31.8(3) . . . . ?
C5 C6 B1 N1 -45.4(3) . . . . ?
C1 C6 B1 N1 138.3(2) . . . . ?
C5 C6 B1 C12 -171.9(2) . . . . ?
C1 C6 B1 C12 11.8(3) . . . . ?
C5 C6 B1 N2 66.3(3) . . . . ?
C1 C6 B1 N2 -110.0(2) . . . . ?
C11 C12 B1 N1 144.0(2) . . . . ?
C7 C12 B1 N1 -41.5(3) . . . . ?
C11 C12 B1 C6 -90.1(3) . . . . ?
C7 C12 B1 C6 84.5(3) . . . . ?
C11 C12 B1 N2 30.7(3) . . . . ?
C7 C12 B1 N2 -154.7(2) . . . . ?
C18 N2 B1 N1 147.5(2) . . . . ?
N3 N2 B1 N1 -35.9(2) . . . . ?
C18 N2 B1 C6 30.6(3) . . . . ?
N3 N2 B1 C6 -152.74(18) . . . . ?
C18 N2 B1 C12 -93.6(2) . . . . ?
N3 N2 B1 C12 83.1(2) . . . . ?
C28 C23 C24 C25 0.2(4) . . . . ?
C1 C6 C5 C4 -2.3(5) . . . . ?
B1 C6 C5 C4 -178.9(3) . . . . ?
C31 C32 C33 C34 1.3(5) . . . . ?
C29 C34 C33 C32 0.6(4) . . . . ?
C33 C32 C31 C30 -1.5(5) . . . . ?
C29 C30 C31 C32 0.0(4) . . . . ?
C23 C24 C25 C26 -0.2(4) . . . . ?
C27 C26 C25 C24 0.6(4) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C12 C11 C10 C9 0.3(5) . . . . ?
C6 C5 C4 C3 2.5(6) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.155

####################################################################### 
# 
# 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_201557111_0m
_database_code_depnum_ccdc_archive 'CCDC 1435545'
_audit_update_record             
;
2016-02-01 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H36 B2 N4'
_chemical_formula_weight         570.33

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                   11.471(3)
_cell_length_b                   22.263(5)
_cell_length_c                   12.589(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.037(4)
_cell_angle_gamma                90
_cell_volume                     3207.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3170
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.45

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9817
_exptl_absorpt_correction_T_max  0.9850
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21117
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.829
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7331
_reflns_number_gt                4044
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0799P)²+0.1157P] 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         7331
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1687
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.001

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 0.3832(2) 0.16722(9) 0.13461(16) 0.0339(5) Uani 1 1 d . . . . .
B2 B 0.3157(2) 0.34440(9) 0.23950(16) 0.0348(5) Uani 1 1 d . . . . .
C1 C 0.4774(2) 0.28280(9) -0.19303(16) 0.0554(6) Uani 1 1 d . . . . .
H1A H 0.5553 0.2807 -0.2161 0.083 Uiso 1 1 calc R U . . .
H1B H 0.4692 0.3185 -0.1515 0.083 Uiso 1 1 calc R U . . .
H1C H 0.4223 0.2838 -0.2541 0.083 Uiso 1 1 calc R U . . .
C2 C 0.45448(17) 0.22888(8) -0.12674(14) 0.0378(4) Uani 1 1 d . . . . .
C3 C 0.46376(17) 0.16884(8) -0.15262(14) 0.0420(5) Uani 1 1 d . . . . .
H3 H 0.4839 0.1541 -0.2180 0.050 Uiso 1 1 calc R U . . .
C4 C 0.43827(17) 0.13370(8) -0.06560(14) 0.0381(4) Uani 1 1 d . . . . .
C5 C 0.42114(16) 0.22892(7) -0.02185(13) 0.0343(4) Uani 1 1 d . . . . .
C6 C 0.39023(16) 0.26864(8) 0.05614(13) 0.0363(4) Uani 1 1 d . . . . .
H6 H 0.3869 0.3101 0.0478 0.044 Uiso 1 1 calc R U . . .
C7 C 0.30876(17) 0.24328(8) 0.31802(13) 0.0363(4) Uani 1 1 d . . . . .
H7 H 0.3114 0.2018 0.3264 0.044 Uiso 1 1 calc R U . . .
C8 C 0.28003(17) 0.28332(8) 0.39664(14) 0.0370(4) Uani 1 1 d . . . . .
C9 C 0.24935(17) 0.28330(9) 0.50245(14) 0.0412(5) Uani 1 1 d . . . . .
C10 C 0.2292(2) 0.22859(10) 0.56820(16) 0.0563(6) Uani 1 1 d . . . . .
H10A H 0.2826 0.2287 0.6304 0.084 Uiso 1 1 calc R U . . .
H10B H 0.2417 0.1932 0.5270 0.084 Uiso 1 1 calc R U . . .
H10C H 0.1504 0.2288 0.5893 0.084 Uiso 1 1 calc R U . . .
C11 C 0.24182(18) 0.34336(9) 0.52863(15) 0.0468(5) Uani 1 1 d . . . . .
H11 H 0.2231 0.3580 0.5945 0.056 Uiso 1 1 calc R U . . .
C12 C 0.26652(18) 0.37863(9) 0.44161(15) 0.0430(5) Uani 1 1 d . . . . .
C13 C 0.2727(2) 0.44528(9) 0.43394(18) 0.0631(7) Uani 1 1 d . . . . .
H13A H 0.3428 0.4566 0.4017 0.095 Uiso 1 1 calc R U . . .
H13B H 0.2732 0.4624 0.5040 0.095 Uiso 1 1 calc R U . . .
H13C H 0.2060 0.4599 0.3912 0.095 Uiso 1 1 calc R U . . .
C14 C 0.4556(2) 0.41478(9) 0.13546(19) 0.0589(6) Uani 1 1 d . . . . .
H14 H 0.3923 0.4251 0.0889 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5651(3) 0.43791(12) 0.1183(3) 0.0850(9) Uani 1 1 d . . . . .
H15 H 0.5741 0.4637 0.0612 0.102 Uiso 1 1 calc R U . . .
C16 C 0.6598(3) 0.42286(15) 0.1852(3) 0.0971(10) Uani 1 1 d . . . . .
H16 H 0.7333 0.4379 0.1731 0.117 Uiso 1 1 calc R U . . .
C17 C 0.6460(2) 0.38550(15) 0.2700(3) 0.0863(9) Uani 1 1 d . . . . .
H17 H 0.7102 0.3751 0.3156 0.104 Uiso 1 1 calc R U . . .
C18 C 0.5365(2) 0.36337(11) 0.28747(19) 0.0606(6) Uani 1 1 d . . . . .
H18 H 0.5281 0.3387 0.3461 0.073 Uiso 1 1 calc R U . . .
C19 C 0.43799(18) 0.37668(8) 0.22026(15) 0.0413(5) Uani 1 1 d . . . . .
C20 C 0.1676(2) 0.42450(9) 0.16002(17) 0.0555(6) Uani 1 1 d . . . . .
H20 H 0.2149 0.4534 0.1946 0.067 Uiso 1 1 calc R U . . .
C21 C 0.0658(3) 0.44240(13) 0.1043(2) 0.0734(8) Uani 1 1 d . . . . .
H21 H 0.0448 0.4828 0.1030 0.088 Uiso 1 1 calc R U . . .
C22 C -0.0048(3) 0.40111(14) 0.0508(2) 0.0744(8) Uani 1 1 d . . . . .
H22 H -0.0734 0.4132 0.0130 0.089 Uiso 1 1 calc R U . . .
C23 C 0.0271(2) 0.34173(12) 0.05360(17) 0.0615(6) Uani 1 1 d . . . . .
H23 H -0.0197 0.3134 0.0170 0.074 Uiso 1 1 calc R U . . .
C24 C 0.12823(18) 0.32399(9) 0.11053(14) 0.0439(5) Uani 1 1 d . . . . .
H24 H 0.1478 0.2834 0.1117 0.053 Uiso 1 1 calc R U . . .
C25 C 0.20212(18) 0.36430(8) 0.16625(14) 0.0389(5) Uani 1 1 d . . . . .
C26 C 0.57095(18) 0.18699(9) 0.26326(14) 0.0435(5) Uani 1 1 d . . . . .
H26 H 0.5543 0.2278 0.2586 0.052 Uiso 1 1 calc R U . . .
C27 C 0.6708(2) 0.16873(12) 0.32285(17) 0.0604(6) Uani 1 1 d . . . . .
H27 H 0.7196 0.1970 0.3576 0.073 Uiso 1 1 calc R U . . .
C28 C 0.6972(2) 0.10880(13) 0.3302(2) 0.0703(7) Uani 1 1 d . . . . .
H28 H 0.7644 0.0962 0.3695 0.084 Uiso 1 1 calc R U . . .
C29 C 0.6246(2) 0.06776(12) 0.2795(2) 0.0684(7) Uani 1 1 d . . . . .
H29 H 0.6428 0.0271 0.2840 0.082 Uiso 1 1 calc R U . . .
C30 C 0.5241(2) 0.08628(9) 0.22142(17) 0.0524(6) Uani 1 1 d . . . . .
H30 H 0.4748 0.0575 0.1889 0.063 Uiso 1 1 calc R U . . .
C31 C 0.49470(17) 0.14675(8) 0.21024(13) 0.0368(4) Uani 1 1 d . . . . .
C32 C 0.26097(18) 0.13382(7) 0.15024(14) 0.0370(4) Uani 1 1 d . . . . .
C33 C 0.2405(2) 0.09764(8) 0.23694(18) 0.0513(5) Uani 1 1 d . . . . .
H33 H 0.3010 0.0912 0.2888 0.062 Uiso 1 1 calc R U . . .
C34 C 0.1331(2) 0.07081(10) 0.2489(2) 0.0663(7) Uani 1 1 d . . . . .
H34 H 0.1226 0.0467 0.3078 0.080 Uiso 1 1 calc R U . . .
C35 C 0.0430(3) 0.07986(12) 0.1743(3) 0.0786(8) Uani 1 1 d . . . . .
H35 H -0.0291 0.0619 0.1819 0.094 Uiso 1 1 calc R U . . .
C36 C 0.0590(2) 0.11544(14) 0.0883(2) 0.0785(8) Uani 1 1 d . . . . .
H36 H -0.0026 0.1221 0.0376 0.094 Uiso 1 1 calc R U . . .
C37 C 0.1667(2) 0.14167(10) 0.07643(18) 0.0574(6) Uani 1 1 d . . . . .
H37 H 0.1762 0.1654 0.0168 0.069 Uiso 1 1 calc R U . . .
C38 C 0.4369(2) 0.06729(9) -0.05622(18) 0.0618(7) Uani 1 1 d . . . . .
H38A H 0.5016 0.0545 -0.0091 0.093 Uiso 1 1 calc R U . . .
H38B H 0.4432 0.0497 -0.1252 0.093 Uiso 1 1 calc R U . . .
H38C H 0.3650 0.0547 -0.0283 0.093 Uiso 1 1 calc R U . . .
N1 N 0.41279(13) 0.17050(6) 0.01464(11) 0.0338(4) Uani 1 1 d . . . . .
N2 N 0.36621(13) 0.24012(6) 0.14368(11) 0.0332(4) Uani 1 1 d . . . . .
N3 N 0.33177(13) 0.27149(6) 0.23024(11) 0.0336(4) Uani 1 1 d . . . . .
N4 N 0.28933(14) 0.34166(6) 0.36031(11) 0.0372(4) 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 1.573(2) . ?
B1 C31 1.606(3) . ?
B1 C32 1.611(3) . ?
B1 N2 1.640(2) . ?
B2 N4 1.573(2) . ?
B2 C25 1.605(3) . ?
B2 C19 1.609(3) . ?
B2 N3 1.639(2) . ?
C1 C2 1.496(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.382(2) . ?
C2 C5 1.400(2) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.349(2) . ?
C4 C38 1.483(3) . ?
C5 N1 1.385(2) . ?
C5 C6 1.386(2) . ?
C6 N2 1.318(2) . ?
C6 H6 0.9300 . ?
C7 N3 1.314(2) . ?
C7 C8 1.389(2) . ?
C7 H7 0.9300 . ?
C8 N4 1.384(2) . ?
C8 C9 1.401(2) . ?
C9 C11 1.381(3) . ?
C9 C10 1.500(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9300 . ?
C12 N4 1.353(2) . ?
C12 C13 1.489(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.388(4) . ?
C14 C19 1.389(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.395(3) . ?
C18 H18 0.9300 . ?
C20 C21 1.379(3) . ?
C20 C25 1.398(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9300 . ?
C26 C27 1.385(3) . ?
C26 C31 1.390(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.364(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.393(3) . ?
C30 H30 0.9300 . ?
C32 C37 1.386(3) . ?
C32 C33 1.390(3) . ?
C33 C34 1.387(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.361(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.364(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.384(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
N2 N3 1.3754(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
N1 B1 C31 111.45(15) . . ?
N1 B1 C32 112.78(15) . . ?
C31 B1 C32 117.40(15) . . ?
N1 B1 N2 93.20(12) . . ?
C31 B1 N2 109.47(15) . . ?
C32 B1 N2 109.85(15) . . ?
N4 B2 C25 111.24(15) . . ?
N4 B2 C19 113.09(15) . . ?
C25 B2 C19 118.11(16) . . ?
N4 B2 N3 93.48(13) . . ?
C25 B2 N3 108.86(15) . . ?
C19 B2 N3 109.17(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C5 104.69(15) . . ?
C3 C2 C1 128.71(17) . . ?
C5 C2 C1 126.58(17) . . ?
C2 C3 C4 109.50(16) . . ?
C2 C3 H3 125.3 . . ?
C4 C3 H3 125.3 . . ?
N1 C4 C3 108.44(15) . . ?
N1 C4 C38 122.80(16) . . ?
C3 C4 C38 128.76(16) . . ?
N1 C5 C6 109.70(15) . . ?
N1 C5 C2 110.01(15) . . ?
C6 C5 C2 140.25(17) . . ?
N2 C6 C5 111.35(16) . . ?
N2 C6 H6 124.3 . . ?
C5 C6 H6 124.3 . . ?
N3 C7 C8 111.37(16) . . ?
N3 C7 H7 124.3 . . ?
C8 C7 H7 124.3 . . ?
N4 C8 C7 109.84(15) . . ?
N4 C8 C9 110.18(15) . . ?
C7 C8 C9 139.91(17) . . ?
C11 C9 C8 104.50(16) . . ?
C11 C9 C10 129.78(17) . . ?
C8 C9 C10 125.71(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 109.78(16) . . ?
C9 C11 H11 125.1 . . ?
C12 C11 H11 125.1 . . ?
N4 C12 C11 108.22(17) . . ?
N4 C12 C13 122.99(18) . . ?
C11 C12 C13 128.76(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 121.9(3) . . ?
C15 C14 H14 119.1 . . ?
C19 C14 H14 119.1 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 122.3(2) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C14 C19 C18 116.1(2) . . ?
C14 C19 B2 124.32(19) . . ?
C18 C19 B2 119.41(18) . . ?
C21 C20 C25 122.2(2) . . ?
C21 C20 H20 118.9 . . ?
C25 C20 H20 118.9 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.1(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C24 120.2(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C25 122.6(2) . . ?
C23 C24 H24 118.7 . . ?
C25 C24 H24 118.7 . . ?
C24 C25 C20 115.49(19) . . ?
C24 C25 B2 123.59(16) . . ?
C20 C25 B2 120.81(18) . . ?
C27 C26 C31 122.7(2) . . ?
C27 C26 H26 118.7 . . ?
C31 C26 H26 118.7 . . ?
C28 C27 C26 119.5(2) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C29 C28 C27 119.8(2) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.4(2) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C31 121.9(2) . . ?
C29 C30 H30 119.1 . . ?
C31 C30 H30 119.1 . . ?
C26 C31 C30 115.78(19) . . ?
C26 C31 B1 123.37(16) . . ?
C30 C31 B1 120.76(18) . . ?
C37 C32 C33 115.6(2) . . ?
C37 C32 B1 120.28(17) . . ?
C33 C32 B1 124.05(18) . . ?
C34 C33 C32 122.4(2) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C35 C34 C33 119.9(2) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 119.7(2) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C37 120.1(3) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C36 C37 C32 122.3(2) . . ?
C36 C37 H37 118.9 . . ?
C32 C37 H37 118.9 . . ?
C4 C38 H38A 109.5 . . ?
C4 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C4 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C4 N1 C5 107.36(14) . . ?
C4 N1 B1 139.81(14) . . ?
C5 N1 B1 112.75(13) . . ?
C6 N2 N3 120.44(14) . . ?
C6 N2 B1 112.69(14) . . ?
N3 N2 B1 126.87(13) . . ?
C7 N3 N2 120.64(14) . . ?
C7 N3 B2 112.54(14) . . ?
N2 N3 B2 126.81(13) . . ?
C12 N4 C8 107.31(15) . . ?
C12 N4 B2 140.22(16) . . ?
C8 N4 B2 112.37(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 177.8(2) . . . . ?
C2 C3 C4 N1 0.1(2) . . . . ?
C2 C3 C4 C38 179.9(2) . . . . ?
C3 C2 C5 N1 1.1(2) . . . . ?
C1 C2 C5 N1 -177.52(19) . . . . ?
C3 C2 C5 C6 -176.2(2) . . . . ?
C1 C2 C5 C6 5.2(4) . . . . ?
N1 C5 C6 N2 2.4(2) . . . . ?
C2 C5 C6 N2 179.7(2) . . . . ?
N3 C7 C8 N4 -2.7(2) . . . . ?
N3 C7 C8 C9 -179.1(2) . . . . ?
N4 C8 C9 C11 -0.6(2) . . . . ?
C7 C8 C9 C11 175.8(3) . . . . ?
N4 C8 C9 C10 178.87(19) . . . . ?
C7 C8 C9 C10 -4.7(4) . . . . ?
C8 C9 C11 C12 0.3(2) . . . . ?
C10 C9 C11 C12 -179.2(2) . . . . ?
C9 C11 C12 N4 0.2(2) . . . . ?
C9 C11 C12 C13 -177.8(2) . . . . ?
C19 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C15 C14 C19 B2 -175.1(2) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C17 C18 C19 B2 174.4(2) . . . . ?
N4 B2 C19 C14 -141.42(18) . . . . ?
C25 B2 C19 C14 -9.0(3) . . . . ?
N3 B2 C19 C14 116.0(2) . . . . ?
N4 B2 C19 C18 43.2(2) . . . . ?
C25 B2 C19 C18 175.57(17) . . . . ?
N3 B2 C19 C18 -59.4(2) . . . . ?
C25 C20 C21 C22 -1.2(4) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C23 C24 C25 C20 -0.6(3) . . . . ?
C23 C24 C25 B2 175.74(18) . . . . ?
C21 C20 C25 C24 1.4(3) . . . . ?
C21 C20 C25 B2 -175.0(2) . . . . ?
N4 B2 C25 C24 -98.17(19) . . . . ?
C19 B2 C25 C24 128.62(19) . . . . ?
N3 B2 C25 C24 3.5(2) . . . . ?
N4 B2 C25 C20 77.9(2) . . . . ?
C19 B2 C25 C20 -55.3(2) . . . . ?
N3 B2 C25 C20 179.57(17) . . . . ?
C31 C26 C27 C28 0.4(3) . . . . ?
C26 C27 C28 C29 -0.5(4) . . . . ?
C27 C28 C29 C30 -0.5(4) . . . . ?
C28 C29 C30 C31 1.6(4) . . . . ?
C27 C26 C31 C30 0.6(3) . . . . ?
C27 C26 C31 B1 -175.83(18) . . . . ?
C29 C30 C31 C26 -1.6(3) . . . . ?
C29 C30 C31 B1 174.95(19) . . . . ?
N1 B1 C31 C26 94.36(19) . . . . ?
C32 B1 C31 C26 -133.40(18) . . . . ?
N2 B1 C31 C26 -7.3(2) . . . . ?
N1 B1 C31 C30 -81.9(2) . . . . ?
C32 B1 C31 C30 50.3(2) . . . . ?
N2 B1 C31 C30 176.39(16) . . . . ?
N1 B1 C32 C37 -37.2(2) . . . . ?
C31 B1 C32 C37 -168.88(17) . . . . ?
N2 B1 C32 C37 65.2(2) . . . . ?
N1 B1 C32 C33 144.79(17) . . . . ?
C31 B1 C32 C33 13.1(3) . . . . ?
N2 B1 C32 C33 -112.75(19) . . . . ?
C37 C32 C33 C34 0.3(3) . . . . ?
B1 C32 C33 C34 178.36(18) . . . . ?
C32 C33 C34 C35 -0.3(3) . . . . ?
C33 C34 C35 C36 -0.2(4) . . . . ?
C34 C35 C36 C37 0.7(4) . . . . ?
C35 C36 C37 C32 -0.8(4) . . . . ?
C33 C32 C37 C36 0.2(3) . . . . ?
B1 C32 C37 C36 -177.9(2) . . . . ?
C3 C4 N1 C5 0.5(2) . . . . ?
C38 C4 N1 C5 -179.28(19) . . . . ?
C3 C4 N1 B1 -175.8(2) . . . . ?
C38 C4 N1 B1 4.4(4) . . . . ?
C6 C5 N1 C4 177.16(16) . . . . ?
C2 C5 N1 C4 -1.0(2) . . . . ?
C6 C5 N1 B1 -5.4(2) . . . . ?
C2 C5 N1 B1 176.44(16) . . . . ?
C31 B1 N1 C4 69.2(3) . . . . ?
C32 B1 N1 C4 -65.3(3) . . . . ?
N2 B1 N1 C4 -178.4(2) . . . . ?
C31 B1 N1 C5 -107.00(17) . . . . ?
C32 B1 N1 C5 118.47(16) . . . . ?
N2 B1 N1 C5 5.37(18) . . . . ?
C5 C6 N2 N3 -178.97(16) . . . . ?
C5 C6 N2 B1 1.4(2) . . . . ?
N1 B1 N2 C6 -3.97(19) . . . . ?
C31 B1 N2 C6 110.13(17) . . . . ?
C32 B1 N2 C6 -119.59(17) . . . . ?
N1 B1 N2 N3 176.43(15) . . . . ?
C31 B1 N2 N3 -69.5(2) . . . . ?
C32 B1 N2 N3 60.8(2) . . . . ?
C8 C7 N3 N2 177.71(16) . . . . ?
C8 C7 N3 B2 -1.7(2) . . . . ?
C6 N2 N3 C7 -179.38(17) . . . . ?
B1 N2 N3 C7 0.2(3) . . . . ?
C6 N2 N3 B2 -0.1(3) . . . . ?
B1 N2 N3 B2 179.52(17) . . . . ?
N4 B2 N3 C7 4.60(19) . . . . ?
C25 B2 N3 C7 -109.25(17) . . . . ?
C19 B2 N3 C7 120.52(17) . . . . ?
N4 B2 N3 N2 -174.77(15) . . . . ?
C25 B2 N3 N2 71.4(2) . . . . ?
C19 B2 N3 N2 -58.8(2) . . . . ?
C11 C12 N4 C8 -0.6(2) . . . . ?
C13 C12 N4 C8 177.6(2) . . . . ?
C11 C12 N4 B2 175.2(2) . . . . ?
C13 C12 N4 B2 -6.7(4) . . . . ?
C7 C8 N4 C12 -176.82(17) . . . . ?
C9 C8 N4 C12 0.7(2) . . . . ?
C7 C8 N4 B2 6.1(2) . . . . ?
C9 C8 N4 B2 -176.33(16) . . . . ?
C25 B2 N4 C12 -70.0(3) . . . . ?
C19 B2 N4 C12 65.7(3) . . . . ?
N3 B2 N4 C12 178.2(2) . . . . ?
C25 B2 N4 C8 105.67(18) . . . . ?
C19 B2 N4 C8 -118.66(17) . . . . ?
N3 B2 N4 C8 -6.12(18) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.047

