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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1485404'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H24 N2'
_chemical_formula_sum            'C21 H24 N2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         304.42

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'

_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                   9.1486(18)
_cell_length_b                   13.496(3)
_cell_length_c                   14.507(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.345(6)
_cell_angle_gamma                90
_cell_volume                     1776.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3018
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11101
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.705
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3239
_reflns_number_gt                2389
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Mercury
_computing_publication_material  enCIFer
_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)+(0.0559P)²+0.7859P] 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         3239
_refine_ls_number_parameters     288
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.952
_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
N1 N 0.46520(14) 0.52950(10) 0.65495(9) 0.0208(3) Uani 1 1 d D . . . .
H1 H 0.5084 0.5456 0.6062 0.025 Uiso 1 1 calc DR U . . .
N2 N 0.36709(14) 0.38157(9) 0.50668(9) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.37650(16) 0.44830(11) 0.66184(10) 0.0168(3) Uani 1 1 d . . . . .
C3 C 0.33010(18) 0.44691(12) 0.74748(11) 0.0209(4) Uani 1 1 d . . . . .
H3 H 0.2684 0.3982 0.7699 0.025 Uiso 1 1 calc R U . . .
C4 C 0.39044(17) 0.53120(11) 0.79710(11) 0.0186(3) Uani 1 1 d . . . . .
C5 C 0.47492(17) 0.58148(12) 0.73725(11) 0.0201(4) Uani 1 1 d . . . . .
C6 C 0.33288(17) 0.37801(11) 0.58908(10) 0.0172(3) Uani 1 1 d . . . . .
H6 H 0.2732 0.3241 0.6037 0.021 Uiso 1 1 calc R U . . .
C7B C 0.3127(8) 0.3002(5) 0.4513(6) 0.0145(5) Uani 0.5 1 d G U P A 2
C8A C 0.1765(8) 0.3151(6) 0.3986(7) 0.0224(12) Uani 0.5 1 d G U P A 2
C9A C 0.1121(8) 0.2395(7) 0.3422(7) 0.0228(16) Uani 0.5 1 d G U P A 2
H9A H 0.0191 0.2497 0.3062 0.027 Uiso 0.5 1 calc R U P A 2
C10A C 0.1839(7) 0.1491(6) 0.3384(6) 0.0146(11) Uani 0.5 1 d G . P A 2
H10A H 0.1399 0.0975 0.2999 0.018 Uiso 0.5 1 calc R U P A 2
C11 C 0.3201(7) 0.1343(4) 0.3911(5) 0.0189(14) Uani 0.5 1 d G U P A 2
H11 H 0.3692 0.0725 0.3885 0.023 Uiso 0.5 1 calc R U P A 2
C12A C 0.3845(7) 0.2098(4) 0.4475(5) 0.0234(12) Uani 0.5 1 d G U P A 2
C13 C 0.0607(5) 0.3999(3) 0.4136(3) 0.0216(9) Uani 0.5 1 d . U P A 1
H13 H 0.0893 0.4202 0.4797 0.026 Uiso 0.5 1 calc R U P A 1
C16 C 0.5522(5) 0.2224(3) 0.4835(3) 0.0227(9) Uani 0.5 1 d . U P A 1
H16 H 0.5822 0.2919 0.5010 0.027 Uiso 0.5 1 calc R U P A 1
C19 C 0.38235(18) 0.56924(12) 0.88624(11) 0.0237(4) Uani 1 1 d . . . . .
H19 H 0.3269 0.5358 0.9278 0.028 Uiso 1 1 calc R U . . .
C20 C 0.45537(19) 0.65506(12) 0.91256(11) 0.0240(4) Uani 1 1 d . . . . .
H20 H 0.4494 0.6818 0.9725 0.029 Uiso 1 1 calc R U . . .
C21 C 0.5385(2) 0.70370(14) 0.85224(12) 0.0315(4) Uani 1 1 d . . . . .
H21 H 0.5880 0.7633 0.8721 0.038 Uiso 1 1 calc R U . . .
C22 C 0.5509(2) 0.66800(14) 0.76505(12) 0.0347(5) Uani 1 1 d . . . . .
H22 H 0.6093 0.7012 0.7250 0.042 Uiso 1 1 calc R U . . .
C17 C 0.6629(5) 0.1811(3) 0.4223(3) 0.0261(9) Uani 0.5 1 d . U P A 1
H17A H 0.7625 0.1841 0.4563 0.039 Uiso 0.5 1 calc R U P A 1
H17B H 0.6589 0.2206 0.3653 0.039 Uiso 0.5 1 calc R U P A 1
H17C H 0.6380 0.1121 0.4061 0.039 Uiso 0.5 1 calc R U P A 1
C15 C -0.1026(5) 0.3727(4) 0.4014(4) 0.0307(11) Uani 0.5 1 d . U P A 1
H15A H -0.1596 0.4277 0.4226 0.046 Uiso 0.5 1 calc R U P A 1
H15B H -0.1172 0.3134 0.4380 0.046 Uiso 0.5 1 calc R U P A 1
H15C H -0.1357 0.3595 0.3356 0.046 Uiso 0.5 1 calc R U P A 1
C18 C 0.5575(5) 0.1623(3) 0.5722(3) 0.0310(10) Uani 0.5 1 d . U P A 1
H18A H 0.5247 0.0944 0.5570 0.046 Uiso 0.5 1 calc R U P A 1
H18B H 0.4925 0.1925 0.6130 0.046 Uiso 0.5 1 calc R U P A 1
H18C H 0.6587 0.1610 0.6040 0.046 Uiso 0.5 1 calc R U P A 1
C14 C 0.0923(4) 0.4858(3) 0.3521(3) 0.0334(8) Uani 0.5 1 d . U P A 1
H14A H 0.0734 0.4655 0.2867 0.050 Uiso 0.5 1 calc R U P A 1
H14B H 0.1956 0.5057 0.3668 0.050 Uiso 0.5 1 calc R U P A 1
H14C H 0.0283 0.5417 0.3628 0.050 Uiso 0.5 1 calc R U P A 1
C13A C 0.0973(5) 0.4153(3) 0.3895(3) 0.0229(9) Uani 0.5 1 d . U P A 2
H13A H 0.1546 0.4618 0.4340 0.027 Uiso 0.5 1 calc R U P A 2
C16A C 0.5322(5) 0.1933(3) 0.5079(4) 0.0236(10) Uani 0.5 1 d . U P A 2
H16A H 0.5729 0.2598 0.5278 0.028 Uiso 0.5 1 calc R U P A 2
C17A C 0.6429(5) 0.1427(4) 0.4537(3) 0.0368(11) Uani 0.5 1 d . U P A 2
H17D H 0.6072 0.0764 0.4349 0.055 Uiso 0.5 1 calc R U P A 2
H17E H 0.7380 0.1373 0.4930 0.055 Uiso 0.5 1 calc R U P A 2
H17F H 0.6548 0.1819 0.3983 0.055 Uiso 0.5 1 calc R U P A 2
C15A C -0.0539(6) 0.4028(3) 0.4215(3) 0.0307(10) Uani 0.5 1 d . U P A 2
H15D H -0.1134 0.3572 0.3795 0.046 Uiso 0.5 1 calc R U P A 2
H15E H -0.1033 0.4673 0.4208 0.046 Uiso 0.5 1 calc R U P A 2
H15F H -0.0424 0.3759 0.4847 0.046 Uiso 0.5 1 calc R U P A 2
C18A C 0.5117(5) 0.1350(4) 0.5950(3) 0.0345(10) Uani 0.5 1 d . U P A 2
H18D H 0.4455 0.1714 0.6309 0.052 Uiso 0.5 1 calc R U P A 2
H18E H 0.6074 0.1259 0.6328 0.052 Uiso 0.5 1 calc R U P A 2
H18F H 0.4688 0.0701 0.5773 0.052 Uiso 0.5 1 calc R U P A 2
C14A C 0.0828(5) 0.4642(3) 0.2935(3) 0.0329(9) Uani 0.5 1 d . U P A 2
H14D H 0.1802 0.4687 0.2725 0.049 Uiso 0.5 1 calc R U P A 2
H14E H 0.0416 0.5309 0.2974 0.049 Uiso 0.5 1 calc R U P A 2
H14F H 0.0173 0.4244 0.2493 0.049 Uiso 0.5 1 calc R U P A 2
C7A C 0.3022(8) 0.3067(5) 0.4431(6) 0.0145(5) Uani 0.5 1 d G U P A 1
C8 C 0.1631(8) 0.3113(6) 0.3919(7) 0.0183(11) Uani 0.5 1 d G U P A 1
C9 C 0.1141(7) 0.2343(7) 0.3322(7) 0.0199(14) Uani 0.5 1 d G U P A 1
H9 H 0.0190 0.2375 0.2972 0.024 Uiso 0.5 1 calc R U P A 1
C10B C 0.2041(7) 0.1527(6) 0.3236(6) 0.0146(11) Uani 0.5 1 d G . P A 1
H10B H 0.1706 0.1001 0.2828 0.018 Uiso 0.5 1 calc R U P A 1
C11A C 0.3432(7) 0.1481(4) 0.3747(5) 0.0205(14) Uani 0.5 1 d G U P A 1
H11A H 0.4047 0.0924 0.3689 0.025 Uiso 0.5 1 calc R U P A 1
C12 C 0.3922(6) 0.2251(4) 0.4345(5) 0.0198(10) Uani 0.5 1 d G U P A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.375(2) . ?
N1 C5 1.378(2) . ?
N1 H1 0.8800 . ?
N2 C6 1.275(2) . ?
N2 C7B 1.414(6) . ?
N2 C7A 1.444(6) . ?
C2 C3 1.363(2) . ?
C2 C6 1.437(2) . ?
C3 C4 1.420(2) . ?
C3 H3 0.9500 . ?
C4 C19 1.402(2) . ?
C4 C5 1.408(2) . ?
C5 C22 1.392(2) . ?
C6 H6 0.9500 . ?
C7B C8A 1.3900 . ?
C7B C12A 1.3900 . ?
C8A C9A 1.3900 . ?
C8A C13A 1.533(7) . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9500 . ?
C10A C11 1.3900 . ?
C10A H10A 0.9500 . ?
C11 C12A 1.3900 . ?
C11 H11 0.9500 . ?
C12A C16A 1.530(6) . ?
C13 C14 1.513(5) . ?
C13 C15 1.526(6) . ?
C13 C8 1.575(7) . ?
C13 H13 1.0000 . ?
C16 C18 1.517(5) . ?
C16 C17 1.535(5) . ?
C16 C12 1.544(6) . ?
C16 H16 1.0000 . ?
C19 C20 1.367(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.372(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13A C15A 1.524(6) . ?
C13A C14A 1.530(6) . ?
C13A H13A 1.0000 . ?
C16A C17A 1.521(6) . ?
C16A C18A 1.520(6) . ?
C16A H16A 1.0000 . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C7A C8 1.3900 . ?
C7A C12 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10B 1.3900 . ?
C9 H9 0.9500 . ?
C10B C11A 1.3900 . ?
C10B H10B 0.9500 . ?
C11A C12 1.3900 . ?
C11A H11A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 108.43(13) . . ?
C2 N1 H1 125.8 . . ?
C5 N1 H1 125.8 . . ?
C6 N2 C7B 113.2(4) . . ?
C6 N2 C7A 116.3(4) . . ?
C3 C2 N1 109.43(13) . . ?
C3 C2 C6 124.79(15) . . ?
N1 C2 C6 125.71(14) . . ?
C2 C3 C4 107.75(14) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C19 C4 C5 119.34(15) . . ?
C19 C4 C3 134.28(15) . . ?
C5 C4 C3 106.38(14) . . ?
N1 C5 C22 130.75(15) . . ?
N1 C5 C4 108.01(14) . . ?
C22 C5 C4 121.24(15) . . ?
N2 C6 C2 125.83(15) . . ?
N2 C6 H6 117.1 . . ?
C2 C6 H6 117.1 . . ?
C8A C7B C12A 120.0 . . ?
C8A C7B N2 115.2(4) . . ?
C12A C7B N2 124.8(4) . . ?
C7B C8A C9A 120.0 . . ?
C7B C8A C13A 123.8(4) . . ?
C9A C8A C13A 115.9(4) . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C11 C10A C9A 120.0 . . ?
C11 C10A H10A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C10A C11 C12A 120.0 . . ?
C10A C11 H11 120.0 . . ?
C12A C11 H11 120.0 . . ?
C11 C12A C7B 120.0 . . ?
C11 C12A C16A 120.5(4) . . ?
C7B C12A C16A 119.5(4) . . ?
C14 C13 C15 111.9(4) . . ?
C14 C13 C8 107.5(6) . . ?
C15 C13 C8 113.1(4) . . ?
C14 C13 H13 108.0 . . ?
C15 C13 H13 108.0 . . ?
C8 C13 H13 108.0 . . ?
C18 C16 C17 110.2(3) . . ?
C18 C16 C12 109.2(4) . . ?
C17 C16 C12 113.5(4) . . ?
C18 C16 H16 107.9 . . ?
C17 C16 H16 107.9 . . ?
C12 C16 H16 107.9 . . ?
C20 C19 C4 119.10(16) . . ?
C20 C19 H19 120.4 . . ?
C4 C19 H19 120.4 . . ?
C19 C20 C21 120.65(15) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 121.94(16) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C5 117.70(16) . . ?
C21 C22 H22 121.2 . . ?
C5 C22 H22 121.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15A C13A C8A 108.3(5) . . ?
C15A C13A C14A 110.4(4) . . ?
C8A C13A C14A 116.4(6) . . ?
C15A C13A H13A 107.1 . . ?
C8A C13A H13A 107.1 . . ?
C14A C13A H13A 107.1 . . ?
C17A C16A C18A 111.0(4) . . ?
C17A C16A C12A 111.6(4) . . ?
C18A C16A C12A 110.9(4) . . ?
C17A C16A H16A 107.7 . . ?
C18A C16A H16A 107.7 . . ?
C12A C16A H16A 107.7 . . ?
C16A C17A H17D 109.5 . . ?
C16A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C16A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C13A C15A H15D 109.5 . . ?
C13A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C13A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C16A C18A H18D 109.5 . . ?
C16A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C16A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C13A C14A H14D 109.5 . . ?
C13A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
C13A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C8 C7A C12 120.0 . . ?
C8 C7A N2 125.7(4) . . ?
C12 C7A N2 114.3(4) . . ?
C9 C8 C7A 120.0 . . ?
C9 C8 C13 122.6(4) . . ?
C7A C8 C13 117.0(4) . . ?
C10B C9 C8 120.0 . . ?
C10B C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11A C10B C9 120.0 . . ?
C11A C10B H10B 120.0 . . ?
C9 C10B H10B 120.0 . . ?
C12 C11A C10B 120.0 . . ?
C12 C11A H11A 120.0 . . ?
C10B C11A H11A 120.0 . . ?
C11A C12 C7A 120.0 . . ?
C11A C12 C16 118.8(4) . . ?
C7A C12 C16 121.0(4) . . ?

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 N1 C2 C3 -0.48(17) . . . . ?
C5 N1 C2 C6 176.73(14) . . . . ?
N1 C2 C3 C4 0.58(18) . . . . ?
C6 C2 C3 C4 -176.66(14) . . . . ?
C2 C3 C4 C19 179.90(17) . . . . ?
C2 C3 C4 C5 -0.46(18) . . . . ?
C2 N1 C5 C22 179.80(18) . . . . ?
C2 N1 C5 C4 0.18(17) . . . . ?
C19 C4 C5 N1 179.88(14) . . . . ?
C3 C4 C5 N1 0.17(17) . . . . ?
C19 C4 C5 C22 0.2(2) . . . . ?
C3 C4 C5 C22 -179.50(16) . . . . ?
C7B N2 C6 C2 177.8(3) . . . . ?
C7A N2 C6 C2 -175.7(3) . . . . ?
C3 C2 C6 N2 175.12(16) . . . . ?
N1 C2 C6 N2 -1.7(2) . . . . ?
C6 N2 C7B C8A 93.0(4) . . . . ?
C6 N2 C7B C12A -86.5(6) . . . . ?
C12A C7B C8A C9A 0.0 . . . . ?
N2 C7B C8A C9A -179.4(7) . . . . ?
C12A C7B C8A C13A -172.7(9) . . . . ?
N2 C7B C8A C13A 7.8(7) . . . . ?
C7B C8A C9A C10A 0.0 . . . . ?
C13A C8A C9A C10A 173.3(9) . . . . ?
C8A C9A C10A C11 0.0 . . . . ?
C9A C10A C11 C12A 0.0 . . . . ?
C10A C11 C12A C7B 0.0 . . . . ?
C10A C11 C12A C16A 178.2(7) . . . . ?
C8A C7B C12A C11 0.0 . . . . ?
N2 C7B C12A C11 179.4(8) . . . . ?
C8A C7B C12A C16A -178.3(6) . . . . ?
N2 C7B C12A C16A 1.1(8) . . . . ?
C5 C4 C19 C20 0.8(2) . . . . ?
C3 C4 C19 C20 -179.59(17) . . . . ?
C4 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C21 C22 C5 1.1(3) . . . . ?
N1 C5 C22 C21 179.26(17) . . . . ?
C4 C5 C22 C21 -1.2(3) . . . . ?
C7B C8A C13A C15A -122.8(6) . . . . ?
C9A C8A C13A C15A 64.2(7) . . . . ?
C7B C8A C13A C14A 112.2(7) . . . . ?
C9A C8A C13A C14A -60.8(6) . . . . ?
C11 C12A C16A C17A 45.7(6) . . . . ?
C7B C12A C16A C17A -136.0(5) . . . . ?
C11 C12A C16A C18A -78.6(6) . . . . ?
C7B C12A C16A C18A 99.6(5) . . . . ?
C6 N2 C7A C8 84.2(5) . . . . ?
C6 N2 C7A C12 -96.4(5) . . . . ?
C12 C7A C8 C9 0.0 . . . . ?
N2 C7A C8 C9 179.4(8) . . . . ?
C12 C7A C8 C13 173.3(8) . . . . ?
N2 C7A C8 C13 -7.4(7) . . . . ?
C14 C13 C8 C9 -98.1(6) . . . . ?
C15 C13 C8 C9 25.9(8) . . . . ?
C14 C13 C8 C7A 88.8(6) . . . . ?
C15 C13 C8 C7A -147.2(5) . . . . ?
C7A C8 C9 C10B 0.0 . . . . ?
C13 C8 C9 C10B -172.9(8) . . . . ?
C8 C9 C10B C11A 0.0 . . . . ?
C9 C10B C11A C12 0.0 . . . . ?
C10B C11A C12 C7A 0.0 . . . . ?
C10B C11A C12 C16 -174.5(6) . . . . ?
C8 C7A C12 C11A 0.0 . . . . ?
N2 C7A C12 C11A -179.4(7) . . . . ?
C8 C7A C12 C16 174.4(6) . . . . ?
N2 C7A C12 C16 -5.1(6) . . . . ?
C18 C16 C12 C11A -86.1(5) . . . . ?
C17 C16 C12 C11A 37.2(6) . . . . ?
C18 C16 C12 C7A 99.5(5) . . . . ?
C17 C16 C12 C7A -137.2(4) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?



















































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1485405'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H16 N2'
_chemical_formula_sum            'C23 H16 N2'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            orange-yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         320.386

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'

_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                   26.1429(14)
_cell_length_b                   5.5789(3)
_cell_length_c                   22.5584(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.477(2)
_cell_angle_gamma                90
_cell_volume                     3212.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2484
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      26.75
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25261
_diffrn_reflns_av_unetI/netI     0.0683
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.691
_diffrn_reflns_theta_max         29.164
_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             4334
_reflns_number_gt                2620
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_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+0.0261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4334
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.003
_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
N1 N 0.95214(5) -0.2553(2) 0.18411(6) 0.0228(3) Uani 1 1 d . . . . .
N2 N 0.94747(5) -0.5259(2) 0.28909(5) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.90551(6) -0.3160(3) 0.19963(6) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.86655(6) -0.1617(3) 0.16690(6) 0.0185(3) Uani 1 1 d . . . . .
C4 C 0.89212(6) -0.0081(3) 0.13242(6) 0.0197(3) Uani 1 1 d . . . . .
C5 C 0.94448(6) -0.0742(3) 0.14348(6) 0.0235(4) Uani 1 1 d . . . . .
H5 H 0.9706 -0.0039 0.1255 0.028 Uiso 1 1 calc R U . . .
C6 C 0.90573(6) -0.4802(3) 0.24833(6) 0.0212(3) Uani 1 1 d . . . . .
H6 H 0.8740 -0.5586 0.2508 0.025 Uiso 1 1 calc R U . . .
C7 C 0.94172(6) -0.6884(3) 0.33552(7) 0.0201(3) Uani 1 1 d . . . . .
C8 C 0.81094(6) -0.1359(3) 0.16446(6) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.78244(6) -0.2915(3) 0.19425(7) 0.0263(4) Uani 1 1 d . . . . .
H9 H 0.8006 -0.4150 0.2193 0.032 Uiso 1 1 calc R U . . .
C10 C 0.72928(6) -0.2707(3) 0.18839(7) 0.0287(4) Uani 1 1 d . . . . .
H10 H 0.7110 -0.3793 0.2088 0.034 Uiso 1 1 calc R U . . .
C11 C 0.70241(6) -0.0896(3) 0.15238(7) 0.0278(4) Uani 1 1 d . . . . .
H11 H 0.6655 -0.0751 0.1477 0.033 Uiso 1 1 calc R U . . .
C12 C 0.72914(6) 0.0685(3) 0.12352(7) 0.0261(4) Uani 1 1 d . . . . .
H12 H 0.7103 0.1937 0.0998 0.031 Uiso 1 1 calc R U . . .
C13 C 0.78349(6) 0.0508(3) 0.12794(6) 0.0198(3) Uani 1 1 d . . . . .
C14 C 0.81092(6) 0.2150(3) 0.09406(6) 0.0200(3) Uani 1 1 d . . . . .
C15 C 0.78520(6) 0.4072(3) 0.05970(7) 0.0258(4) Uani 1 1 d . . . . .
H15 H 0.7491 0.4341 0.0586 0.031 Uiso 1 1 calc R U . . .
C16 C 0.81110(7) 0.5574(3) 0.02754(7) 0.0287(4) Uani 1 1 d . . . . .
H16 H 0.7928 0.6862 0.0048 0.034 Uiso 1 1 calc R U . . .
C17 C 0.86370(6) 0.5214(3) 0.02829(7) 0.0283(4) Uani 1 1 d . . . . .
H17 H 0.8814 0.6239 0.0057 0.034 Uiso 1 1 calc R U . . .
C18 C 0.89022(6) 0.3366(3) 0.06200(6) 0.0240(4) Uani 1 1 d . . . . .
H18 H 0.9264 0.3131 0.0628 0.029 Uiso 1 1 calc R U . . .
C19 C 0.86454(6) 0.1822(3) 0.09521(6) 0.0199(3) Uani 1 1 d . . . . .
C20 C 0.91399(6) -0.9016(3) 0.32395(7) 0.0254(4) Uani 1 1 d . . . . .
H20 H 0.8992 -0.9471 0.2833 0.030 Uiso 1 1 calc R U . . .
C21 C 0.90775(7) -1.0482(3) 0.37140(7) 0.0317(4) Uani 1 1 d . . . . .
H21 H 0.8883 -1.1928 0.3631 0.038 Uiso 1 1 calc R U . . .
C22 C 0.92972(7) -0.9851(3) 0.43101(7) 0.0341(4) Uani 1 1 d . . . . .
H22 H 0.9250 -1.0848 0.4636 0.041 Uiso 1 1 calc R U . . .
C23 C 0.95858(7) -0.7757(3) 0.44261(7) 0.0307(4) Uani 1 1 d . . . . .
H23 H 0.9743 -0.7333 0.4833 0.037 Uiso 1 1 calc R U . . .
C24 C 0.96477(6) -0.6279(3) 0.39548(6) 0.0244(4) Uani 1 1 d . . . . .
H24 H 0.9847 -0.4848 0.4039 0.029 Uiso 1 1 calc R U . . .
H01 H 0.9847(8) -0.337(4) 0.1977(9) 0.065(7) 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
N1 C5 1.3495(19) . ?
N1 C2 1.3811(19) . ?
N1 H01 0.95(2) . ?
N2 C6 1.2916(18) . ?
N2 C7 1.4178(18) . ?
C2 C3 1.414(2) . ?
C2 C6 1.429(2) . ?
C3 C4 1.4182(19) . ?
C3 C8 1.450(2) . ?
C4 C5 1.387(2) . ?
C4 C19 1.446(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C20 1.388(2) . ?
C7 C24 1.398(2) . ?
C8 C9 1.406(2) . ?
C8 C13 1.422(2) . ?
C9 C10 1.372(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.406(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4745(19) . ?
C14 C15 1.406(2) . ?
C14 C19 1.409(2) . ?
C15 C16 1.379(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.404(2) . ?
C18 H18 0.9500 . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 110.26(13) . . ?
C5 N1 H01 124.5(12) . . ?
C2 N1 H01 125.1(12) . . ?
C6 N2 C7 116.36(13) . . ?
N1 C2 C3 107.10(13) . . ?
N1 C2 C6 119.67(13) . . ?
C3 C2 C6 132.39(14) . . ?
C2 C3 C4 106.41(13) . . ?
C2 C3 C8 133.13(13) . . ?
C4 C3 C8 120.45(13) . . ?
C5 C4 C3 107.72(13) . . ?
C5 C4 C19 130.44(14) . . ?
C3 C4 C19 121.82(13) . . ?
N1 C5 C4 108.48(13) . . ?
N1 C5 H5 125.8 . . ?
C4 C5 H5 125.8 . . ?
N2 C6 C2 122.42(14) . . ?
N2 C6 H6 118.8 . . ?
C2 C6 H6 118.8 . . ?
C20 C7 C24 119.18(14) . . ?
C20 C7 N2 122.93(13) . . ?
C24 C7 N2 117.88(13) . . ?
C9 C8 C13 118.42(14) . . ?
C9 C8 C3 123.44(14) . . ?
C13 C8 C3 118.09(13) . . ?
C10 C9 C8 122.14(15) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 119.48(15) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.97(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 122.08(14) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C8 117.90(13) . . ?
C12 C13 C14 121.11(13) . . ?
C8 C13 C14 120.95(13) . . ?
C15 C14 C19 117.70(13) . . ?
C15 C14 C13 122.09(14) . . ?
C19 C14 C13 120.21(13) . . ?
C16 C15 C14 121.53(15) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 120.29(15) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.69(15) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.83(15) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C14 119.95(14) . . ?
C18 C19 C4 121.63(14) . . ?
C14 C19 C4 118.40(13) . . ?
C21 C20 C7 120.33(15) . . ?
C21 C20 H20 119.8 . . ?
C7 C20 H20 119.8 . . ?
C20 C21 C22 120.38(16) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.42(15) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 120.50(15) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C7 120.15(15) . . ?
C23 C24 H24 119.9 . . ?
C7 C24 H24 119.9 . . ?

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 N1 C2 C3 -0.45(16) . . . . ?
C5 N1 C2 C6 -171.21(13) . . . . ?
N1 C2 C3 C4 -0.58(15) . . . . ?
C6 C2 C3 C4 168.53(15) . . . . ?
N1 C2 C3 C8 -179.16(14) . . . . ?
C6 C2 C3 C8 -10.1(3) . . . . ?
C2 C3 C4 C5 1.38(16) . . . . ?
C8 C3 C4 C5 -179.82(12) . . . . ?
C2 C3 C4 C19 -177.09(12) . . . . ?
C8 C3 C4 C19 1.7(2) . . . . ?
C2 N1 C5 C4 1.34(17) . . . . ?
C3 C4 C5 N1 -1.68(16) . . . . ?
C19 C4 C5 N1 176.62(14) . . . . ?
C7 N2 C6 C2 178.66(13) . . . . ?
N1 C2 C6 N2 19.2(2) . . . . ?
C3 C2 C6 N2 -148.79(16) . . . . ?
C6 N2 C7 C20 44.88(19) . . . . ?
C6 N2 C7 C24 -134.47(14) . . . . ?
C2 C3 C8 C9 -5.9(2) . . . . ?
C4 C3 C8 C9 175.70(14) . . . . ?
C2 C3 C8 C13 176.80(15) . . . . ?
C4 C3 C8 C13 -1.62(19) . . . . ?
C13 C8 C9 C10 1.0(2) . . . . ?
C3 C8 C9 C10 -176.30(14) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
C11 C12 C13 C8 -1.0(2) . . . . ?
C11 C12 C13 C14 176.85(14) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
C3 C8 C13 C12 177.18(13) . . . . ?
C9 C8 C13 C14 -178.09(13) . . . . ?
C3 C8 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C15 5.0(2) . . . . ?
C8 C13 C14 C15 -177.27(13) . . . . ?
C12 C13 C14 C19 -174.84(13) . . . . ?
C8 C13 C14 C19 2.9(2) . . . . ?
C19 C14 C15 C16 0.7(2) . . . . ?
C13 C14 C15 C16 -179.09(14) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 C18 -0.8(2) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C17 C18 C19 C14 0.3(2) . . . . ?
C17 C18 C19 C4 -177.97(14) . . . . ?
C15 C14 C19 C18 -1.0(2) . . . . ?
C13 C14 C19 C18 178.89(13) . . . . ?
C15 C14 C19 C4 177.35(13) . . . . ?
C13 C14 C19 C4 -2.81(19) . . . . ?
C5 C4 C19 C18 0.8(2) . . . . ?
C3 C4 C19 C18 178.84(14) . . . . ?
C5 C4 C19 C14 -177.52(14) . . . . ?
C3 C4 C19 C14 0.6(2) . . . . ?
C24 C7 C20 C21 2.2(2) . . . . ?
N2 C7 C20 C21 -177.15(14) . . . . ?
C7 C20 C21 C22 -0.8(2) . . . . ?
C20 C21 C22 C23 -0.9(2) . . . . ?
C21 C22 C23 C24 1.2(2) . . . . ?
C22 C23 C24 C7 0.2(2) . . . . ?
C20 C7 C24 C23 -1.9(2) . . . . ?
N2 C7 C24 C23 177.48(14) . . . . ?

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1485406'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C33 H33 B N2'
_chemical_formula_sum            'C33 H33 B N2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         468.42

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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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, z+1/2'

_cell_length_a                   10.6591(9)
_cell_length_b                   8.7127(7)
_cell_length_c                   14.2325(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.856(5)
_cell_angle_gamma                90
_cell_volume                     1321.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3628
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      24.70
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12089
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.741
_diffrn_reflns_theta_max         25.724
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4881
_reflns_number_gt                4038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.991

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.3000P)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       0.22(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   ?
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P n'
_symmetry_int_tables_number      7
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4881
_refine_ls_number_parameters     327
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.1080
_refine_ls_wR_factor_ref         0.3277
_refine_ls_wR_factor_gt          0.3148
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.980
_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
N1 N 0.3945(5) 0.3059(7) 0.8549(4) 0.0295(14) Uani 1 1 d . . . . .
N2 N 0.2201(6) 0.4615(6) 0.8943(4) 0.0275(13) Uani 1 1 d . . . . .
C2 C 0.4306(7) 0.4481(9) 0.8892(6) 0.0342(17) Uani 1 1 d . . . . .
C3 C 0.5592(7) 0.4510(9) 0.9025(6) 0.0375(18) Uani 1 1 d . . . . .
H3 H 0.6075 0.5354 0.9249 0.045 Uiso 1 1 calc R U . . .
C4 C 0.6054(7) 0.3073(10) 0.8770(6) 0.0365(17) Uani 1 1 d . . . . .
C5 C 0.4987(7) 0.2188(10) 0.8503(5) 0.0357(17) Uani 1 1 d . . . . .
C7 C 0.7250(7) 0.2367(12) 0.8767(7) 0.045(2) Uani 1 1 d . . . . .
H7 H 0.7976 0.2947 0.8930 0.053 Uiso 1 1 calc R U . . .
C6 C 0.3241(7) 0.5364(9) 0.9096(5) 0.0319(16) Uani 1 1 d . . . . .
H6 H 0.3277 0.6390 0.9320 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7360(8) 0.0886(12) 0.8536(7) 0.046(2) Uani 1 1 d . . . . .
H8 H 0.8164 0.0414 0.8549 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6275(8) 0.0003(11) 0.8270(6) 0.0420(19) Uani 1 1 d . . . . .
H9 H 0.6377 -0.1046 0.8104 0.050 Uiso 1 1 calc R U . . .
C10 C 0.5093(8) 0.0630(9) 0.8246(6) 0.0360(17) Uani 1 1 d . . . . .
H10 H 0.4379 0.0042 0.8065 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1007(7) 0.5345(8) 0.8965(5) 0.0285(15) Uani 1 1 d . . . . .
C12 C 0.0236(7) 0.5183(8) 0.9751(6) 0.0327(16) Uani 1 1 d . . . . .
C13 C -0.0931(7) 0.5880(10) 0.9728(7) 0.0402(19) Uani 1 1 d . . . . .
H13 H -0.1465 0.5780 1.0253 0.048 Uiso 1 1 calc R U . . .
C14 C -0.1326(7) 0.6704(9) 0.8970(7) 0.0404(19) Uani 1 1 d . . . . .
H14 H -0.2137 0.7156 0.8965 0.048 Uiso 1 1 calc R U . . .
C15 C -0.0556(8) 0.6890(9) 0.8206(7) 0.0417(19) Uani 1 1 d . . . . .
H15 H -0.0856 0.7471 0.7684 0.050 Uiso 1 1 calc R U . . .
C16 C 0.0631(7) 0.6264(9) 0.8173(5) 0.0342(17) Uani 1 1 d . . . . .
C17 C 0.1486(8) 0.6540(8) 0.7373(5) 0.0347(17) Uani 1 1 d . . . . .
H17 H 0.2169 0.5753 0.7402 0.042 Uiso 1 1 calc R U . . .
C18 C 0.2090(10) 0.8133(10) 0.7461(7) 0.047(2) Uani 1 1 d . . . . .
H18A H 0.2650 0.8302 0.6932 0.070 Uiso 1 1 calc R U . . .
H18B H 0.1432 0.8920 0.7457 0.070 Uiso 1 1 calc R U . . .
H18C H 0.2572 0.8194 0.8052 0.070 Uiso 1 1 calc R U . . .
C19 C 0.0832(12) 0.6421(16) 0.6417(7) 0.065(3) Uani 1 1 d . . . . .
H19A H 0.1440 0.6613 0.5921 0.098 Uiso 1 1 calc R U . . .
H19B H 0.0477 0.5390 0.6339 0.098 Uiso 1 1 calc R U . . .
H19C H 0.0158 0.7184 0.6375 0.098 Uiso 1 1 calc R U . . .
C20 C 0.0713(8) 0.4354(10) 1.0634(6) 0.0406(19) Uani 1 1 d . . . . .
H20 H 0.1380 0.3614 1.0444 0.049 Uiso 1 1 calc R U . . .
C21 C 0.1283(13) 0.5466(14) 1.1337(8) 0.064(3) Uani 1 1 d . . . . .
H21A H 0.1946 0.6060 1.1035 0.096 Uiso 1 1 calc R U . . .
H21B H 0.0632 0.6164 1.1561 0.096 Uiso 1 1 calc R U . . .
H21C H 0.1641 0.4893 1.1869 0.096 Uiso 1 1 calc R U . . .
C22 C -0.0299(11) 0.3466(13) 1.1127(9) 0.062(3) Uani 1 1 d . . . . .
H22A H -0.0687 0.2735 1.0688 0.092 Uiso 1 1 calc R U . . .
H22B H 0.0071 0.2908 1.1661 0.092 Uiso 1 1 calc R U . . .
H22C H -0.0939 0.4179 1.1353 0.092 Uiso 1 1 calc R U . . .
C23 C 0.2147(7) 0.1630(8) 0.9367(5) 0.0300(15) Uani 1 1 d . . . . .
C24 C 0.2918(8) 0.1471(10) 1.0186(6) 0.0379(18) Uani 1 1 d . . . . .
H24 H 0.3664 0.2066 1.0222 0.045 Uiso 1 1 calc R U . . .
C25 C 0.2665(10) 0.0531(10) 1.0920(7) 0.048(2) Uani 1 1 d . . . . .
H25 H 0.3196 0.0520 1.1461 0.058 Uiso 1 1 calc R U . . .
C26 C 0.1605(11) -0.0426(11) 1.0867(7) 0.056(3) Uani 1 1 d . . . . .
H26 H 0.1417 -0.1106 1.1368 0.067 Uiso 1 1 calc R U . . .
C27 C 0.0840(10) -0.0363(10) 1.0074(6) 0.049(2) Uani 1 1 d . . . . .
H27 H 0.0124 -0.1009 1.0029 0.059 Uiso 1 1 calc R U . . .
C28 C 0.1113(8) 0.0652(10) 0.9332(6) 0.0382(18) Uani 1 1 d . . . . .
H28 H 0.0577 0.0668 0.8793 0.046 Uiso 1 1 calc R U . . .
C29 C 0.1832(7) 0.2553(8) 0.7556(5) 0.0304(16) Uani 1 1 d . . . . .
C30 C 0.2518(8) 0.2067(9) 0.6787(6) 0.0369(18) Uani 1 1 d . . . . .
H30 H 0.3408 0.2050 0.6834 0.044 Uiso 1 1 calc R U . . .
C31 C 0.1947(11) 0.1612(11) 0.5962(7) 0.051(2) Uani 1 1 d . . . . .
H31 H 0.2441 0.1252 0.5457 0.061 Uiso 1 1 calc R U . . .
C32 C 0.0658(10) 0.1676(11) 0.5862(7) 0.050(2) Uani 1 1 d . . . . .
H32 H 0.0265 0.1339 0.5295 0.060 Uiso 1 1 calc R U . . .
C33 C -0.0049(9) 0.2224(12) 0.6576(7) 0.048(2) Uani 1 1 d . . . . .
H33 H -0.0931 0.2337 0.6494 0.057 Uiso 1 1 calc R U . . .
C34 C 0.0520(8) 0.2614(10) 0.7421(6) 0.0402(19) Uani 1 1 d . . . . .
H34 H 0.0012 0.2934 0.7927 0.048 Uiso 1 1 calc R U . . .
B1 B 0.2484(7) 0.2858(9) 0.8556(6) 0.0283(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.348(10) . ?
N1 C2 1.384(10) . ?
N1 B1 1.567(10) . ?
N2 C6 1.302(10) . ?
N2 C11 1.423(9) . ?
N2 B1 1.657(10) . ?
C2 C3 1.382(11) . ?
C2 C6 1.404(11) . ?
C3 C4 1.395(12) . ?
C3 H3 0.9500 . ?
C4 C7 1.416(11) . ?
C4 C5 1.420(12) . ?
C5 C10 1.410(12) . ?
C7 C8 1.337(15) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.436(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(11) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.404(11) . ?
C11 C16 1.436(11) . ?
C12 C13 1.384(11) . ?
C12 C20 1.529(12) . ?
C13 C14 1.358(14) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.488(11) . ?
C17 C19 1.524(13) . ?
C17 C18 1.534(12) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22 1.510(14) . ?
C20 C21 1.513(15) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.393(11) . ?
C23 C24 1.423(11) . ?
C23 B1 1.618(11) . ?
C24 C25 1.358(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.405(14) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(15) . ?
C26 H26 0.9500 . ?
C27 C28 1.411(12) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.391(11) . ?
C29 C34 1.410(11) . ?
C29 B1 1.597(11) . ?
C30 C31 1.374(14) . ?
C30 H30 0.9500 . ?
C31 C32 1.380(16) . ?
C31 H31 0.9500 . ?
C32 C33 1.362(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.381(13) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 107.2(6) . . ?
C5 N1 B1 139.2(6) . . ?
C2 N1 B1 111.6(6) . . ?
C6 N2 C11 122.2(6) . . ?
C6 N2 B1 111.1(6) . . ?
C11 N2 B1 126.0(5) . . ?
C3 C2 N1 109.5(7) . . ?
C3 C2 C6 139.9(8) . . ?
N1 C2 C6 110.0(6) . . ?
C2 C3 C4 107.5(7) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
C3 C4 C7 135.4(8) . . ?
C3 C4 C5 105.8(7) . . ?
C7 C4 C5 118.7(8) . . ?
N1 C5 C10 128.6(7) . . ?
N1 C5 C4 109.8(7) . . ?
C10 C5 C4 121.7(7) . . ?
C8 C7 C4 120.1(8) . . ?
C8 C7 H7 119.9 . . ?
C4 C7 H7 119.9 . . ?
N2 C6 C2 112.3(7) . . ?
N2 C6 H6 123.8 . . ?
C2 C6 H6 123.8 . . ?
C7 C8 C9 120.6(7) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 121.9(8) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C5 117.0(7) . . ?
C9 C10 H10 121.5 . . ?
C5 C10 H10 121.5 . . ?
C12 C11 N2 120.5(6) . . ?
C12 C11 C16 121.4(7) . . ?
N2 C11 C16 118.1(7) . . ?
C13 C12 C11 118.3(7) . . ?
C13 C12 C20 120.9(7) . . ?
C11 C12 C20 120.7(7) . . ?
C14 C13 C12 121.2(8) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.4(7) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 122.5(8) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C11 116.0(7) . . ?
C15 C16 C17 122.4(7) . . ?
C11 C16 C17 121.6(7) . . ?
C16 C17 C19 113.3(7) . . ?
C16 C17 C18 110.1(6) . . ?
C19 C17 C18 108.7(8) . . ?
C16 C17 H17 108.2 . . ?
C19 C17 H17 108.2 . . ?
C18 C17 H17 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C21 107.7(9) . . ?
C22 C20 C12 113.2(8) . . ?
C21 C20 C12 111.5(8) . . ?
C22 C20 H20 108.1 . . ?
C21 C20 H20 108.1 . . ?
C12 C20 H20 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 114.6(7) . . ?
C28 C23 B1 124.3(7) . . ?
C24 C23 B1 121.1(7) . . ?
C25 C24 C23 124.8(8) . . ?
C25 C24 H24 117.6 . . ?
C23 C24 H24 117.6 . . ?
C24 C25 C26 119.1(9) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C27 C26 C25 118.9(8) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C28 120.7(8) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C23 C28 C27 121.9(8) . . ?
C23 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C30 C29 C34 115.9(7) . . ?
C30 C29 B1 121.7(7) . . ?
C34 C29 B1 122.2(7) . . ?
C31 C30 C29 122.0(8) . . ?
C31 C30 H30 119.0 . . ?
C29 C30 H30 119.0 . . ?
C30 C31 C32 120.3(9) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C31 119.9(9) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 119.7(8) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C34 C29 122.1(8) . . ?
C33 C34 H34 119.0 . . ?
C29 C34 H34 119.0 . . ?
N1 B1 C29 115.6(6) . . ?
N1 B1 C23 108.0(6) . . ?
C29 B1 C23 115.3(6) . . ?
N1 B1 N2 94.9(5) . . ?
C29 B1 N2 111.8(6) . . ?
C23 B1 N2 109.3(6) . . ?

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 N1 C2 C3 2.3(8) . . . . ?
B1 N1 C2 C3 169.8(6) . . . . ?
C5 N1 C2 C6 -170.8(6) . . . . ?
B1 N1 C2 C6 -3.4(9) . . . . ?
N1 C2 C3 C4 -0.6(9) . . . . ?
C6 C2 C3 C4 169.4(10) . . . . ?
C2 C3 C4 C7 -177.9(9) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C2 N1 C5 C10 176.3(8) . . . . ?
B1 N1 C5 C10 14.3(14) . . . . ?
C2 N1 C5 C4 -3.2(8) . . . . ?
B1 N1 C5 C4 -165.2(8) . . . . ?
C3 C4 C5 N1 2.8(9) . . . . ?
C7 C4 C5 N1 -179.9(7) . . . . ?
C3 C4 C5 C10 -176.7(7) . . . . ?
C7 C4 C5 C10 0.6(11) . . . . ?
C3 C4 C7 C8 174.8(10) . . . . ?
C5 C4 C7 C8 -1.4(12) . . . . ?
C11 N2 C6 C2 -170.4(6) . . . . ?
B1 N2 C6 C2 0.0(8) . . . . ?
C3 C2 C6 N2 -167.8(10) . . . . ?
N1 C2 C6 N2 2.1(9) . . . . ?
C4 C7 C8 C9 1.3(14) . . . . ?
C7 C8 C9 C10 -0.4(14) . . . . ?
C8 C9 C10 C5 -0.4(13) . . . . ?
N1 C5 C10 C9 -179.1(8) . . . . ?
C4 C5 C10 C9 0.3(12) . . . . ?
C6 N2 C11 C12 -102.2(8) . . . . ?
B1 N2 C11 C12 88.9(9) . . . . ?
C6 N2 C11 C16 76.7(9) . . . . ?
B1 N2 C11 C16 -92.2(8) . . . . ?
N2 C11 C12 C13 -178.3(7) . . . . ?
C16 C11 C12 C13 2.8(11) . . . . ?
N2 C11 C12 C20 6.0(10) . . . . ?
C16 C11 C12 C20 -172.9(7) . . . . ?
C11 C12 C13 C14 -0.2(12) . . . . ?
C20 C12 C13 C14 175.6(8) . . . . ?
C12 C13 C14 C15 -1.2(13) . . . . ?
C13 C14 C15 C16 -0.1(13) . . . . ?
C14 C15 C16 C11 2.6(12) . . . . ?
C14 C15 C16 C17 -176.4(7) . . . . ?
C12 C11 C16 C15 -4.0(11) . . . . ?
N2 C11 C16 C15 177.1(6) . . . . ?
C12 C11 C16 C17 175.0(7) . . . . ?
N2 C11 C16 C17 -3.9(10) . . . . ?
C15 C16 C17 C19 -43.6(11) . . . . ?
C11 C16 C17 C19 137.4(9) . . . . ?
C15 C16 C17 C18 78.3(10) . . . . ?
C11 C16 C17 C18 -100.7(9) . . . . ?
C13 C12 C20 C22 38.9(11) . . . . ?
C11 C12 C20 C22 -145.5(8) . . . . ?
C13 C12 C20 C21 -82.7(10) . . . . ?
C11 C12 C20 C21 92.9(9) . . . . ?
C28 C23 C24 C25 -4.0(12) . . . . ?
B1 C23 C24 C25 176.2(8) . . . . ?
C23 C24 C25 C26 3.4(14) . . . . ?
C24 C25 C26 C27 -1.0(14) . . . . ?
C25 C26 C27 C28 -0.4(15) . . . . ?
C24 C23 C28 C27 2.4(12) . . . . ?
B1 C23 C28 C27 -177.8(8) . . . . ?
C26 C27 C28 C23 -0.4(15) . . . . ?
C34 C29 C30 C31 -2.7(12) . . . . ?
B1 C29 C30 C31 171.4(8) . . . . ?
C29 C30 C31 C32 2.3(14) . . . . ?
C30 C31 C32 C33 1.4(15) . . . . ?
C31 C32 C33 C34 -4.4(15) . . . . ?
C32 C33 C34 C29 3.9(14) . . . . ?
C30 C29 C34 C33 -0.3(12) . . . . ?
B1 C29 C34 C33 -174.4(8) . . . . ?
C5 N1 B1 C29 -78.6(11) . . . . ?
C2 N1 B1 C29 119.9(7) . . . . ?
C5 N1 B1 C23 52.3(11) . . . . ?
C2 N1 B1 C23 -109.2(7) . . . . ?
C5 N1 B1 N2 164.4(8) . . . . ?
C2 N1 B1 N2 2.9(7) . . . . ?
C30 C29 B1 N1 17.6(10) . . . . ?
C34 C29 B1 N1 -168.7(7) . . . . ?
C30 C29 B1 C23 -109.8(8) . . . . ?
C34 C29 B1 C23 63.9(10) . . . . ?
C30 C29 B1 N2 124.6(7) . . . . ?
C34 C29 B1 N2 -61.7(9) . . . . ?
C28 C23 B1 N1 -149.8(7) . . . . ?
C24 C23 B1 N1 29.9(9) . . . . ?
C28 C23 B1 C29 -18.7(11) . . . . ?
C24 C23 B1 C29 161.0(7) . . . . ?
C28 C23 B1 N2 108.2(8) . . . . ?
C24 C23 B1 N2 -72.1(8) . . . . ?
C6 N2 B1 N1 -1.7(7) . . . . ?
C11 N2 B1 N1 168.2(6) . . . . ?
C6 N2 B1 C29 -121.8(6) . . . . ?
C11 N2 B1 C29 48.1(9) . . . . ?
C6 N2 B1 C23 109.3(7) . . . . ?
C11 N2 B1 C23 -80.8(8) . . . . ?

_refine_diff_density_max         0.699
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.134

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1485407'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C27 H21 B N2'
_chemical_formula_sum            'C27 H21 B N2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         384.27

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                   8.9836(3)
_cell_length_b                   13.3666(4)
_cell_length_c                   17.2368(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.218(2)
_cell_angle_gamma                90
_cell_volume                     2064.19(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6914
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.63
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   'SADABS (Shlecdrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29573
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.048
_diffrn_reflns_theta_max         28.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5152
_reflns_number_gt                3456
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_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)+(0.0599P)²+0.1728P] 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         5152
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_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
N1 N 0.92245(12) 0.29757(8) 0.48089(6) 0.0295(3) Uani 1 1 d . . . . .
N2 N 0.77151(12) 0.42221(8) 0.53140(6) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.88811(15) 0.37145(10) 0.42639(8) 0.0317(3) Uani 1 1 d . . . . .
C3 C 0.93689(16) 0.34685(11) 0.35518(8) 0.0353(3) Uani 1 1 d . . . . .
H3 H 0.9267 0.3856 0.3089 0.042 Uiso 1 1 calc R U . . .
C4 C 1.00530(15) 0.25215(10) 0.36483(8) 0.0320(3) Uani 1 1 d . . . . .
C5 C 0.99304(14) 0.22318(10) 0.44402(8) 0.0297(3) Uani 1 1 d . . . . .
C6 C 0.80117(14) 0.44559(10) 0.46114(8) 0.0318(3) Uani 1 1 d . . . . .
H6 H 0.7684 0.5056 0.4357 0.038 Uiso 1 1 calc R U . . .
C7 C 0.68531(14) 0.48710(10) 0.57684(8) 0.0292(3) Uani 1 1 d . . . . .
C8 C 0.57643(15) 0.44776(10) 0.62073(8) 0.0337(3) Uani 1 1 d . . . . .
H8 H 0.5566 0.3779 0.6197 0.040 Uiso 1 1 calc R U . . .
C9 C 0.49667(15) 0.51051(11) 0.66609(8) 0.0372(3) Uani 1 1 d . . . . .
H9 H 0.4225 0.4835 0.6966 0.045 Uiso 1 1 calc R U . . .
C10 C 0.52385(16) 0.61203(11) 0.66740(9) 0.0399(4) Uani 1 1 d . . . . .
H10 H 0.4692 0.6548 0.6989 0.048 Uiso 1 1 calc R U . . .
C11 C 0.63058(17) 0.65086(11) 0.62280(10) 0.0434(4) Uani 1 1 d . . . . .
H11 H 0.6485 0.7209 0.6232 0.052 Uiso 1 1 calc R U . . .
C12 C 0.71224(16) 0.58934(10) 0.57740(9) 0.0361(3) Uani 1 1 d . . . . .
H12 H 0.7861 0.6168 0.5469 0.043 Uiso 1 1 calc R U . . .
C13 C 1.07677(16) 0.18671(11) 0.31590(8) 0.0375(3) Uani 1 1 d . . . . .
H13 H 1.0870 0.2041 0.2631 0.045 Uiso 1 1 calc R U . . .
C14 C 1.13175(16) 0.09744(11) 0.34488(9) 0.0388(4) Uani 1 1 d . . . . .
H14 H 1.1793 0.0529 0.3115 0.047 Uiso 1 1 calc R U . . .
C15 C 1.11921(16) 0.07060(11) 0.42274(9) 0.0379(3) Uani 1 1 d . . . . .
H15 H 1.1594 0.0086 0.4412 0.045 Uiso 1 1 calc R U . . .
C16 C 1.05006(16) 0.13206(10) 0.47294(8) 0.0345(3) Uani 1 1 d . . . . .
H16 H 1.0413 0.1133 0.5256 0.041 Uiso 1 1 calc R U . . .
C17 C 0.97111(14) 0.33311(9) 0.63143(8) 0.0268(3) Uani 1 1 d . . . . .
C18 C 1.12042(15) 0.30429(10) 0.62867(8) 0.0323(3) Uani 1 1 d . . . . .
H18 H 1.1533 0.2790 0.5813 0.039 Uiso 1 1 calc R U . . .
C19 C 1.22182(16) 0.31164(11) 0.69316(9) 0.0389(3) Uani 1 1 d . . . . .
H19 H 1.3220 0.2905 0.6895 0.047 Uiso 1 1 calc R U . . .
C20 C 1.17874(16) 0.34921(11) 0.76228(9) 0.0379(3) Uani 1 1 d . . . . .
H20 H 1.2486 0.3547 0.8062 0.046 Uiso 1 1 calc R U . . .
C21 C 1.03264(16) 0.37886(10) 0.76698(8) 0.0350(3) Uani 1 1 d . . . . .
H21 H 1.0013 0.4050 0.8144 0.042 Uiso 1 1 calc R U . . .
C22 C 0.93139(15) 0.37060(10) 0.70261(8) 0.0317(3) Uani 1 1 d . . . . .
H22 H 0.8312 0.3912 0.7071 0.038 Uiso 1 1 calc R U . . .
C23 C 0.72409(14) 0.23304(9) 0.57188(8) 0.0279(3) Uani 1 1 d . . . . .
C24 C 0.71333(15) 0.18109(9) 0.64103(8) 0.0303(3) Uani 1 1 d . . . . .
H24 H 0.7871 0.1915 0.6826 0.036 Uiso 1 1 calc R U . . .
C25 C 0.59793(17) 0.11442(10) 0.65122(9) 0.0374(3) Uani 1 1 d . . . . .
H25 H 0.5933 0.0805 0.6994 0.045 Uiso 1 1 calc R U . . .
C26 C 0.49042(18) 0.09737(12) 0.59182(10) 0.0459(4) Uani 1 1 d . . . . .
H26 H 0.4101 0.0529 0.5990 0.055 Uiso 1 1 calc R U . . .
C27 C 0.5006(2) 0.14559(13) 0.52164(10) 0.0529(4) Uani 1 1 d . . . . .
H27 H 0.4279 0.1333 0.4799 0.063 Uiso 1 1 calc R U . . .
C28 C 0.61560(17) 0.21144(11) 0.51195(9) 0.0423(4) Uani 1 1 d . . . . .
H28 H 0.6214 0.2432 0.4630 0.051 Uiso 1 1 calc R U . . .
B1 B 0.85091(16) 0.31570(11) 0.55878(9) 0.0270(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
N1 C5 1.3616(17) . ?
N1 C2 1.3822(17) . ?
N1 B1 1.5495(18) . ?
N2 C6 1.2971(17) . ?
N2 C7 1.4335(17) . ?
N2 B1 1.6458(18) . ?
C2 C3 1.3734(19) . ?
C2 C6 1.4211(19) . ?
C3 C4 1.412(2) . ?
C3 H3 0.9500 . ?
C4 C13 1.403(2) . ?
C4 C5 1.4309(19) . ?
C5 C16 1.399(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3836(18) . ?
C7 C12 1.3877(19) . ?
C8 C9 1.3822(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.374(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.372(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.3957(19) . ?
C17 C18 1.3997(18) . ?
C17 B1 1.609(2) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3863(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.3890(18) . ?
C23 C28 1.3973(19) . ?
C23 B1 1.6147(19) . ?
C24 C25 1.3880(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.374(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(2) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 107.03(11) . . ?
C5 N1 B1 139.09(11) . . ?
C2 N1 B1 113.01(11) . . ?
C6 N2 C7 121.37(11) . . ?
C6 N2 B1 111.20(11) . . ?
C7 N2 B1 127.36(10) . . ?
C3 C2 N1 111.49(12) . . ?
C3 C2 C6 139.91(13) . . ?
N1 C2 C6 108.30(11) . . ?
C2 C3 C4 105.92(12) . . ?
C2 C3 H3 127.0 . . ?
C4 C3 H3 127.0 . . ?
C13 C4 C3 134.65(13) . . ?
C13 C4 C5 118.39(13) . . ?
C3 C4 C5 106.96(12) . . ?
N1 C5 C16 129.82(13) . . ?
N1 C5 C4 108.60(12) . . ?
C16 C5 C4 121.58(13) . . ?
N2 C6 C2 112.48(12) . . ?
N2 C6 H6 123.8 . . ?
C2 C6 H6 123.8 . . ?
C8 C7 C12 120.02(13) . . ?
C8 C7 N2 120.05(12) . . ?
C12 C7 N2 119.92(12) . . ?
C9 C8 C7 119.70(13) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.52(14) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.52(14) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.87(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 119.35(14) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C14 C13 C4 119.47(13) . . ?
C14 C13 H13 120.3 . . ?
C4 C13 H13 120.3 . . ?
C13 C14 C15 121.28(14) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 121.45(14) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C5 117.83(13) . . ?
C15 C16 H16 121.1 . . ?
C5 C16 H16 121.1 . . ?
C22 C17 C18 115.87(12) . . ?
C22 C17 B1 122.39(12) . . ?
C18 C17 B1 121.57(12) . . ?
C19 C18 C17 121.83(13) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C20 C19 C18 120.67(13) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.06(13) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C22 120.09(13) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 122.48(13) . . ?
C21 C22 H22 118.8 . . ?
C17 C22 H22 118.8 . . ?
C24 C23 C28 116.26(12) . . ?
C24 C23 B1 123.81(12) . . ?
C28 C23 B1 119.93(12) . . ?
C25 C24 C23 121.96(13) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C26 C25 C24 120.20(14) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.19(14) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C28 C27 C26 120.25(15) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C23 122.09(14) . . ?
C27 C28 H28 119.0 . . ?
C23 C28 H28 119.0 . . ?
N1 B1 C17 113.54(11) . . ?
N1 B1 C23 110.86(11) . . ?
C17 B1 C23 115.47(11) . . ?
N1 B1 N2 94.90(9) . . ?
C17 B1 N2 110.48(10) . . ?
C23 B1 N2 109.67(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 -0.79(15) . . . . ?
B1 N1 C2 C3 -172.23(11) . . . . ?
C5 N1 C2 C6 174.25(11) . . . . ?
B1 N1 C2 C6 2.81(15) . . . . ?
N1 C2 C3 C4 0.25(15) . . . . ?
C6 C2 C3 C4 -172.43(16) . . . . ?
C2 C3 C4 C13 -179.63(15) . . . . ?
C2 C3 C4 C5 0.36(15) . . . . ?
C2 N1 C5 C16 -179.84(13) . . . . ?
B1 N1 C5 C16 -11.9(3) . . . . ?
C2 N1 C5 C4 0.99(14) . . . . ?
B1 N1 C5 C4 168.92(14) . . . . ?
C13 C4 C5 N1 179.14(11) . . . . ?
C3 C4 C5 N1 -0.85(15) . . . . ?
C13 C4 C5 C16 -0.10(19) . . . . ?
C3 C4 C5 C16 179.90(12) . . . . ?
C7 N2 C6 C2 179.84(11) . . . . ?
B1 N2 C6 C2 2.40(15) . . . . ?
C3 C2 C6 N2 169.54(16) . . . . ?
N1 C2 C6 N2 -3.29(15) . . . . ?
C6 N2 C7 C8 137.32(13) . . . . ?
B1 N2 C7 C8 -45.68(17) . . . . ?
C6 N2 C7 C12 -43.35(17) . . . . ?
B1 N2 C7 C12 133.65(13) . . . . ?
C12 C7 C8 C9 -1.1(2) . . . . ?
N2 C7 C8 C9 178.19(12) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C7 0.2(2) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
N2 C7 C12 C11 -178.59(12) . . . . ?
C3 C4 C13 C14 -179.69(15) . . . . ?
C5 C4 C13 C14 0.32(19) . . . . ?
C4 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C14 C15 C16 C5 -0.5(2) . . . . ?
N1 C5 C16 C15 -178.90(13) . . . . ?
C4 C5 C16 C15 0.2(2) . . . . ?
C22 C17 C18 C19 0.70(19) . . . . ?
B1 C17 C18 C19 -174.69(12) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C20 C21 C22 C17 -0.2(2) . . . . ?
C18 C17 C22 C21 -0.15(19) . . . . ?
B1 C17 C22 C21 175.21(12) . . . . ?
C28 C23 C24 C25 -2.5(2) . . . . ?
B1 C23 C24 C25 176.56(12) . . . . ?
C23 C24 C25 C26 0.5(2) . . . . ?
C24 C25 C26 C27 1.4(2) . . . . ?
C25 C26 C27 C28 -1.3(3) . . . . ?
C26 C27 C28 C23 -0.8(3) . . . . ?
C24 C23 C28 C27 2.7(2) . . . . ?
B1 C23 C28 C27 -176.44(15) . . . . ?
C5 N1 B1 C17 76.33(19) . . . . ?
C2 N1 B1 C17 -116.22(12) . . . . ?
C5 N1 B1 C23 -55.6(2) . . . . ?
C2 N1 B1 C23 111.86(12) . . . . ?
C5 N1 B1 N2 -168.81(14) . . . . ?
C2 N1 B1 N2 -1.36(12) . . . . ?
C22 C17 B1 N1 166.55(11) . . . . ?
C18 C17 B1 N1 -18.36(17) . . . . ?
C22 C17 B1 C23 -63.82(16) . . . . ?
C18 C17 B1 C23 111.27(14) . . . . ?
C22 C17 B1 N2 61.34(15) . . . . ?
C18 C17 B1 N2 -123.56(12) . . . . ?
C24 C23 B1 N1 132.71(13) . . . . ?
C28 C23 B1 N1 -48.25(16) . . . . ?
C24 C23 B1 C17 1.79(18) . . . . ?
C28 C23 B1 C17 -179.17(13) . . . . ?
C24 C23 B1 N2 -123.79(13) . . . . ?
C28 C23 B1 N2 55.25(16) . . . . ?
C6 N2 B1 N1 -0.65(13) . . . . ?
C7 N2 B1 N1 -177.90(11) . . . . ?
C6 N2 B1 C17 116.74(12) . . . . ?
C7 N2 B1 C17 -60.51(15) . . . . ?
C6 N2 B1 C23 -114.86(12) . . . . ?
C7 N2 B1 C23 67.88(15) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1485408'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C35 H25 B N2'
_chemical_formula_sum            'C35 H25 B N2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            brown-yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         484.38

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/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                   12.2486(9)
_cell_length_b                   9.0701(7)
_cell_length_c                   21.8347(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.772(4)
_cell_angle_gamma                90
_cell_volume                     2424.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2792
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.63
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18074
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.538
_diffrn_reflns_theta_max         25.776
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4554
_reflns_number_gt                3129
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_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)+(0.0839P)²+0.4811P] 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         4554
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
N1 N 0.84755(15) 0.2913(2) 0.10476(8) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.72543(14) 0.1819(2) 0.03282(8) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.88000(18) 0.1489(2) 0.09101(10) 0.0218(5) Uani 1 1 d . . . . .
C3 C 0.97251(18) 0.1130(3) 0.12906(10) 0.0218(5) Uani 1 1 d . . . . .
C4 C 0.99240(17) 0.2394(2) 0.16522(10) 0.0223(5) Uani 1 1 d . . . . .
C5 C 0.91308(17) 0.3453(3) 0.14900(10) 0.0222(5) Uani 1 1 d . . . . .
H5 H 0.9072 0.4404 0.1668 0.027 Uiso 1 1 calc R U . . .
C6 C 0.80578(17) 0.0900(3) 0.04792(10) 0.0224(5) Uani 1 1 d . . . . .
H6 H 0.8122 -0.0062 0.0311 0.027 Uiso 1 1 calc R U . . .
C7 C 0.64511(18) 0.1471(2) -0.01360(10) 0.0224(5) Uani 1 1 d . . . . .
C8 C 0.67370(19) 0.0706(3) -0.06553(10) 0.0265(5) Uani 1 1 d . . . . .
H8 H 0.7476 0.0430 -0.0708 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5941(2) 0.0339(3) -0.11039(11) 0.0312(6) Uani 1 1 d . . . . .
H9 H 0.6135 -0.0197 -0.1458 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4880(2) 0.0758(3) -0.10269(12) 0.0340(6) Uani 1 1 d . . . . .
H10 H 0.4337 0.0518 -0.1331 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4591(2) 0.1532(3) -0.05070(11) 0.0295(6) Uani 1 1 d . . . . .
H11 H 0.3853 0.1810 -0.0455 0.035 Uiso 1 1 calc R U . . .
C12 C 0.53753(18) 0.1895(3) -0.00684(11) 0.0250(5) Uani 1 1 d . . . . .
H12 H 0.5178 0.2439 0.0283 0.030 Uiso 1 1 calc R U . . .
C13 C 1.03801(17) -0.0180(3) 0.13665(10) 0.0224(5) Uani 1 1 d . . . . .
C14 C 1.0198(2) -0.1456(3) 0.10151(11) 0.0309(6) Uani 1 1 d . . . . .
H14 H 0.9652 -0.1450 0.0696 0.037 Uiso 1 1 calc R U . . .
C15 C 1.0790(2) -0.2699(3) 0.11234(12) 0.0331(6) Uani 1 1 d . . . . .
H15 H 1.0645 -0.3554 0.0883 0.040 Uiso 1 1 calc R U . . .
C16 C 1.1604(2) -0.2742(3) 0.15807(12) 0.0334(6) Uani 1 1 d . . . . .
H16 H 1.2018 -0.3614 0.1651 0.040 Uiso 1 1 calc R U . . .
C17 C 1.18030(19) -0.1496(3) 0.19327(11) 0.0286(6) Uani 1 1 d . . . . .
H17 H 1.2347 -0.1531 0.2252 0.034 Uiso 1 1 calc R U . . .
C18 C 1.12215(18) -0.0182(3) 0.18300(10) 0.0232(5) Uani 1 1 d . . . . .
C19 C 1.14713(16) 0.1165(2) 0.21904(9) 0.0177(5) Uani 1 1 d . . . . .
C20 C 1.23360(19) 0.1221(3) 0.26186(11) 0.0272(6) Uani 1 1 d . . . . .
H20 H 1.2782 0.0376 0.2684 0.033 Uiso 1 1 calc R U . . .
C21 C 1.2554(2) 0.2497(3) 0.29507(11) 0.0319(6) Uani 1 1 d . . . . .
H21 H 1.3131 0.2502 0.3252 0.038 Uiso 1 1 calc R U . . .
C22 C 1.19452(19) 0.3760(3) 0.28505(11) 0.0300(6) Uani 1 1 d . . . . .
H22 H 1.2118 0.4639 0.3070 0.036 Uiso 1 1 calc R U . . .
C23 C 1.10804(18) 0.3734(3) 0.24272(10) 0.0266(6) Uani 1 1 d . . . . .
H23 H 1.0655 0.4598 0.2360 0.032 Uiso 1 1 calc R U . . .
C24 C 1.08255(18) 0.2451(3) 0.20967(10) 0.0221(5) Uani 1 1 d . . . . .
C25 C 0.76133(17) 0.4687(3) 0.02004(10) 0.0232(5) Uani 1 1 d . . . . .
C26 C 0.86004(19) 0.5433(3) 0.01848(11) 0.0299(6) Uani 1 1 d . . . . .
H26 H 0.9170 0.5160 0.0468 0.036 Uiso 1 1 calc R U . . .
C27 C 0.8790(2) 0.6567(3) -0.02292(11) 0.0319(6) Uani 1 1 d . . . . .
H27 H 0.9481 0.7045 -0.0226 0.038 Uiso 1 1 calc R U . . .
C28 C 0.7988(2) 0.6992(3) -0.06381(11) 0.0298(6) Uani 1 1 d . . . . .
H28 H 0.8114 0.7768 -0.0920 0.036 Uiso 1 1 calc R U . . .
C29 C 0.6996(2) 0.6288(3) -0.06382(11) 0.0329(6) Uani 1 1 d . . . . .
H29 H 0.6431 0.6582 -0.0920 0.039 Uiso 1 1 calc R U . . .
C30 C 0.68138(19) 0.5151(3) -0.02303(11) 0.0283(6) Uani 1 1 d . . . . .
H30 H 0.6124 0.4671 -0.0243 0.034 Uiso 1 1 calc R U . . .
C31 C 0.64441(18) 0.3672(3) 0.11628(10) 0.0226(5) Uani 1 1 d . . . . .
C32 C 0.58103(17) 0.4956(3) 0.11569(10) 0.0243(5) Uani 1 1 d . . . . .
H32 H 0.5928 0.5674 0.0849 0.029 Uiso 1 1 calc R U . . .
C33 C 0.50151(19) 0.5222(3) 0.15837(11) 0.0304(6) Uani 1 1 d . . . . .
H33 H 0.4604 0.6110 0.1567 0.036 Uiso 1 1 calc R U . . .
C34 C 0.4826(2) 0.4187(3) 0.20344(11) 0.0341(6) Uani 1 1 d . . . . .
H34 H 0.4281 0.4354 0.2327 0.041 Uiso 1 1 calc R U . . .
C35 C 0.5444(2) 0.2895(3) 0.20545(11) 0.0326(6) Uani 1 1 d . . . . .
H35 H 0.5323 0.2177 0.2362 0.039 Uiso 1 1 calc R U . . .
C36 C 0.6229(2) 0.2661(3) 0.16280(11) 0.0301(6) Uani 1 1 d . . . . .
H36 H 0.6643 0.1776 0.1650 0.036 Uiso 1 1 calc R U . . .
B1 B 0.7402(2) 0.3385(3) 0.06838(12) 0.0220(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.330(3) . ?
N1 C2 1.387(3) . ?
N1 B1 1.574(3) . ?
N2 C6 1.324(3) . ?
N2 C7 1.426(3) . ?
N2 B1 1.626(3) . ?
C2 C6 1.394(3) . ?
C2 C3 1.422(3) . ?
C3 C4 1.408(3) . ?
C3 C13 1.440(3) . ?
C4 C5 1.404(3) . ?
C4 C24 1.448(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 C12 1.385(3) . ?
C8 C9 1.401(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.403(3) . ?
C13 C18 1.422(3) . ?
C14 C15 1.358(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.403(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.480(3) . ?
C19 C20 1.392(3) . ?
C19 C24 1.421(3) . ?
C20 C21 1.387(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.399(3) . ?
C23 H23 0.9500 . ?
C25 C26 1.387(3) . ?
C25 C30 1.401(3) . ?
C25 B1 1.610(3) . ?
C26 C27 1.394(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.363(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.373(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.400(3) . ?
C31 C36 1.399(3) . ?
C31 B1 1.617(3) . ?
C32 C33 1.390(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.385(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.395(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.375(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 109.23(19) . . ?
C5 N1 B1 137.9(2) . . ?
C2 N1 B1 112.60(18) . . ?
C6 N2 C7 121.93(19) . . ?
C6 N2 B1 111.11(18) . . ?
C7 N2 B1 126.66(18) . . ?
N1 C2 C6 108.5(2) . . ?
N1 C2 C3 108.36(19) . . ?
C6 C2 C3 142.9(2) . . ?
C4 C3 C2 105.21(19) . . ?
C4 C3 C13 121.4(2) . . ?
C2 C3 C13 133.4(2) . . ?
C5 C4 C3 108.0(2) . . ?
C5 C4 C24 130.7(2) . . ?
C3 C4 C24 121.3(2) . . ?
N1 C5 C4 109.2(2) . . ?
N1 C5 H5 125.4 . . ?
C4 C5 H5 125.4 . . ?
N2 C6 C2 113.0(2) . . ?
N2 C6 H6 123.5 . . ?
C2 C6 H6 123.5 . . ?
C8 C7 C12 119.5(2) . . ?
C8 C7 N2 120.5(2) . . ?
C12 C7 N2 120.05(19) . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 119.2(2) . . ?
C14 C13 C3 122.6(2) . . ?
C18 C13 C3 118.2(2) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 117.9(2) . . ?
C17 C18 C19 121.4(2) . . ?
C13 C18 C19 120.7(2) . . ?
C20 C19 C24 118.4(2) . . ?
C20 C19 C18 121.9(2) . . ?
C24 C19 C18 119.75(19) . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 119.6(2) . . ?
C23 C24 C4 121.9(2) . . ?
C19 C24 C4 118.5(2) . . ?
C26 C25 C30 115.4(2) . . ?
C26 C25 B1 122.1(2) . . ?
C30 C25 B1 122.5(2) . . ?
C25 C26 C27 122.6(2) . . ?
C25 C26 H26 118.7 . . ?
C27 C26 H26 118.7 . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 119.3(2) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C28 C29 C30 120.4(2) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 122.2(2) . . ?
C29 C30 H30 118.9 . . ?
C25 C30 H30 118.9 . . ?
C32 C31 C36 115.8(2) . . ?
C32 C31 B1 122.8(2) . . ?
C36 C31 B1 121.4(2) . . ?
C33 C32 C31 122.6(2) . . ?
C33 C32 H32 118.7 . . ?
C31 C32 H32 118.7 . . ?
C34 C33 C32 119.6(2) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 119.3(2) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C36 C35 C34 119.9(2) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C31 122.8(2) . . ?
C35 C36 H36 118.6 . . ?
C31 C36 H36 118.6 . . ?
N1 B1 C31 109.19(18) . . ?
N1 B1 C25 112.45(18) . . ?
C31 B1 C25 116.13(19) . . ?
N1 B1 N2 94.74(17) . . ?
C31 B1 N2 112.13(18) . . ?
C25 B1 N2 110.21(18) . . ?

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 N1 C2 C6 175.61(18) . . . . ?
B1 N1 C2 C6 0.2(2) . . . . ?
C5 N1 C2 C3 -0.5(2) . . . . ?
B1 N1 C2 C3 -175.95(18) . . . . ?
N1 C2 C3 C4 0.0(2) . . . . ?
C6 C2 C3 C4 -173.9(3) . . . . ?
N1 C2 C3 C13 177.7(2) . . . . ?
C6 C2 C3 C13 3.8(5) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C13 C3 C4 C5 -177.57(19) . . . . ?
C2 C3 C4 C24 -179.19(19) . . . . ?
C13 C3 C4 C24 2.7(3) . . . . ?
C2 N1 C5 C4 0.8(2) . . . . ?
B1 N1 C5 C4 174.5(2) . . . . ?
C3 C4 C5 N1 -0.8(2) . . . . ?
C24 C4 C5 N1 178.8(2) . . . . ?
C7 N2 C6 C2 175.57(18) . . . . ?
B1 N2 C6 C2 1.5(3) . . . . ?
N1 C2 C6 N2 -1.0(2) . . . . ?
C3 C2 C6 N2 172.8(3) . . . . ?
C6 N2 C7 C8 -36.9(3) . . . . ?
B1 N2 C7 C8 136.2(2) . . . . ?
C6 N2 C7 C12 142.9(2) . . . . ?
B1 N2 C7 C12 -44.0(3) . . . . ?
C12 C7 C8 C9 -1.2(3) . . . . ?
N2 C7 C8 C9 178.6(2) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C7 -1.1(4) . . . . ?
C8 C7 C12 C11 1.4(3) . . . . ?
N2 C7 C12 C11 -178.4(2) . . . . ?
C4 C3 C13 C14 179.7(2) . . . . ?
C2 C3 C13 C14 2.3(4) . . . . ?
C4 C3 C13 C18 1.6(3) . . . . ?
C2 C3 C13 C18 -175.8(2) . . . . ?
C18 C13 C14 C15 1.9(3) . . . . ?
C3 C13 C14 C15 -176.1(2) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 -1.5(4) . . . . ?
C16 C17 C18 C13 2.6(3) . . . . ?
C16 C17 C18 C19 -177.3(2) . . . . ?
C14 C13 C18 C17 -2.8(3) . . . . ?
C3 C13 C18 C17 175.3(2) . . . . ?
C14 C13 C18 C19 177.17(19) . . . . ?
C3 C13 C18 C19 -4.7(3) . . . . ?
C17 C18 C19 C20 4.2(3) . . . . ?
C13 C18 C19 C20 -175.7(2) . . . . ?
C17 C18 C19 C24 -176.5(2) . . . . ?
C13 C18 C19 C24 3.5(3) . . . . ?
C24 C19 C20 C21 0.7(3) . . . . ?
C18 C19 C20 C21 180.0(2) . . . . ?
C19 C20 C21 C22 -2.3(4) . . . . ?
C20 C21 C22 C23 2.3(4) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C19 -0.9(3) . . . . ?
C22 C23 C24 C4 179.9(2) . . . . ?
C20 C19 C24 C23 0.9(3) . . . . ?
C18 C19 C24 C23 -178.42(19) . . . . ?
C20 C19 C24 C4 -179.89(19) . . . . ?
C18 C19 C24 C4 0.8(3) . . . . ?
C5 C4 C24 C23 -4.3(4) . . . . ?
C3 C4 C24 C23 175.3(2) . . . . ?
C5 C4 C24 C19 176.5(2) . . . . ?
C3 C4 C24 C19 -3.9(3) . . . . ?
C30 C25 C26 C27 0.0(3) . . . . ?
B1 C25 C26 C27 -179.6(2) . . . . ?
C25 C26 C27 C28 0.5(4) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
C27 C28 C29 C30 -0.4(4) . . . . ?
C28 C29 C30 C25 0.9(4) . . . . ?
C26 C25 C30 C29 -0.7(3) . . . . ?
B1 C25 C30 C29 179.0(2) . . . . ?
C36 C31 C32 C33 0.0(3) . . . . ?
B1 C31 C32 C33 -177.5(2) . . . . ?
C31 C32 C33 C34 -0.3(4) . . . . ?
C32 C33 C34 C35 0.4(4) . . . . ?
C33 C34 C35 C36 -0.1(4) . . . . ?
C34 C35 C36 C31 -0.2(4) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
B1 C31 C36 C35 177.9(2) . . . . ?
C5 N1 B1 C31 -57.6(3) . . . . ?
C2 N1 B1 C31 116.0(2) . . . . ?
C5 N1 B1 C25 72.8(3) . . . . ?
C2 N1 B1 C25 -113.6(2) . . . . ?
C5 N1 B1 N2 -173.0(2) . . . . ?
C2 N1 B1 N2 0.6(2) . . . . ?
C32 C31 B1 N1 129.7(2) . . . . ?
C36 C31 B1 N1 -47.7(3) . . . . ?
C32 C31 B1 C25 1.3(3) . . . . ?
C36 C31 B1 C25 -176.1(2) . . . . ?
C32 C31 B1 N2 -126.7(2) . . . . ?
C36 C31 B1 N2 56.0(3) . . . . ?
C26 C25 B1 N1 -9.1(3) . . . . ?
C30 C25 B1 N1 171.4(2) . . . . ?
C26 C25 B1 C31 117.7(2) . . . . ?
C30 C25 B1 C31 -61.8(3) . . . . ?
C26 C25 B1 N2 -113.4(2) . . . . ?
C30 C25 B1 N2 67.0(3) . . . . ?
C6 N2 B1 N1 -1.2(2) . . . . ?
C7 N2 B1 N1 -174.94(18) . . . . ?
C6 N2 B1 C31 -114.1(2) . . . . ?
C7 N2 B1 C31 72.1(3) . . . . ?
C6 N2 B1 C25 114.8(2) . . . . ?
C7 N2 B1 C25 -58.9(3) . . . . ?

_refine_diff_density_max         1.032
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.054

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?


