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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1446083'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 B N5'
_chemical_formula_weight         437.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 '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                   16.5717(10)
_cell_length_b                   22.3081(13)
_cell_length_c                   11.7698(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.701(4)
_cell_angle_gamma                90
_cell_volume                     4288.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7164
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      65.59

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.641
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25267
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.705
_diffrn_reflns_theta_max         62.985
_diffrn_reflns_theta_full        62.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6842
_reflns_number_gt                5366
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+2.5670P] 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         6842
_refine_ls_number_parameters     617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_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
B1 B 0.50925(13) 0.38030(10) 0.82380(18) 0.0254(5) Uani 1 1 d . . . . .
B2 B 0.01042(13) 0.37491(10) 0.34251(19) 0.0281(5) Uani 1 1 d . . . . .
C1 C 0.55522(11) 0.47364(9) 0.70232(16) 0.0267(4) Uani 1 1 d . . . . .
C2 C 0.61398(11) 0.52317(8) 0.73149(16) 0.0265(4) Uani 1 1 d . . . . .
C3 C 0.64813(11) 0.56287(9) 0.66267(18) 0.0316(5) Uani 1 1 d . . . . .
H3 H 0.6334 0.5621 0.5811 0.038 Uiso 1 1 calc R U . . .
C4 C 0.70469(12) 0.60384(9) 0.71733(18) 0.0353(5) Uani 1 1 d . . . . .
H4 H 0.7297 0.6313 0.6722 0.042 Uiso 1 1 calc R U . . .
C5 C 0.72560(12) 0.60560(9) 0.83659(18) 0.0348(5) Uani 1 1 d . . . . .
H5 H 0.7639 0.6347 0.8713 0.042 Uiso 1 1 calc R U . . .
C6 C 0.69169(11) 0.56569(9) 0.90634(17) 0.0302(4) Uani 1 1 d . . . . .
H6 H 0.7060 0.5667 0.9879 0.036 Uiso 1 1 calc R U . . .
C7 C 0.63593(10) 0.52437(8) 0.85087(16) 0.0255(4) Uani 1 1 d . . . . .
C8 C 0.59276(10) 0.47490(8) 0.89614(15) 0.0240(4) Uani 1 1 d . . . . .
C9 C 0.55321(10) 0.41656(8) 1.03347(15) 0.0238(4) Uani 1 1 d . . . . .
C10 C 0.54791(11) 0.39785(9) 1.15078(16) 0.0254(4) Uani 1 1 d . . . . .
C11 C 0.58532(11) 0.41985(9) 1.25705(16) 0.0295(4) Uani 1 1 d . . . . .
H11 H 0.6224 0.4526 1.2627 0.035 Uiso 1 1 calc R U . . .
C12 C 0.56633(12) 0.39197(9) 1.35471(17) 0.0329(5) Uani 1 1 d . . . . .
H12 H 0.5908 0.4059 1.4288 0.039 Uiso 1 1 calc R U . . .
C13 C 0.51192(12) 0.34381(9) 1.34580(17) 0.0330(5) Uani 1 1 d . . . . .
H13 H 0.5002 0.3254 1.4140 0.040 Uiso 1 1 calc R U . . .
C14 C 0.47464(12) 0.32225(9) 1.23926(16) 0.0309(5) Uani 1 1 d . . . . .
H14 H 0.4372 0.2897 1.2332 0.037 Uiso 1 1 calc R U . . .
C15 C 0.49398(11) 0.34978(9) 1.14237(16) 0.0265(4) Uani 1 1 d . . . . .
C16 C 0.46612(11) 0.33759(9) 1.01854(16) 0.0257(4) Uani 1 1 d . . . . .
C17 C 0.57501(11) 0.33067(8) 0.79767(15) 0.0247(4) Uani 1 1 d . . . . .
C18 C 0.58925(11) 0.31930(9) 0.68523(16) 0.0283(4) Uani 1 1 d . . . . .
H18 H 0.5581 0.3406 0.6229 0.034 Uiso 1 1 calc R U . . .
C19 C 0.64694(11) 0.27832(9) 0.66214(17) 0.0326(5) Uani 1 1 d . . . . .
H19 H 0.6543 0.2717 0.5848 0.039 Uiso 1 1 calc R U . . .
C20 C 0.69376(12) 0.24699(9) 0.75027(18) 0.0343(5) Uani 1 1 d . . . . .
H20 H 0.7332 0.2187 0.7342 0.041 Uiso 1 1 calc R U . . .
C21 C 0.68264(11) 0.25714(9) 0.86219(18) 0.0324(5) Uani 1 1 d . . . . .
H21 H 0.7147 0.2360 0.9239 0.039 Uiso 1 1 calc R U . . .
C22 C 0.62418(11) 0.29849(9) 0.88477(16) 0.0276(4) Uani 1 1 d . . . . .
H22 H 0.6176 0.3050 0.9624 0.033 Uiso 1 1 calc R U . . .
C23 C 0.41808(11) 0.37554(8) 0.74820(15) 0.0248(4) Uani 1 1 d . . . . .
C24 C 0.39572(11) 0.33210(9) 0.66291(16) 0.0269(4) Uani 1 1 d . . . . .
H24 H 0.4348 0.3027 0.6504 0.032 Uiso 1 1 calc R U . . .
C25 C 0.31846(11) 0.33046(9) 0.59609(16) 0.0300(5) Uani 1 1 d . . . . .
H25 H 0.3053 0.3003 0.5390 0.036 Uiso 1 1 calc R U . . .
C26 C 0.26066(11) 0.37258(9) 0.61233(17) 0.0328(5) Uani 1 1 d . . . . .
H26 H 0.2079 0.3719 0.5659 0.039 Uiso 1 1 calc R U . . .
C27 C 0.28016(11) 0.41606(9) 0.69704(17) 0.0328(5) Uani 1 1 d . . . . .
H27 H 0.2406 0.4451 0.7091 0.039 Uiso 1 1 calc R U . . .
C28 C 0.35755(11) 0.41693(9) 0.76401(16) 0.0280(4) Uani 1 1 d . . . . .
H28 H 0.3698 0.4465 0.8224 0.034 Uiso 1 1 calc R U . . .
C29 C 0.08351(11) 0.46142(9) 0.23504(16) 0.0283(4) Uani 1 1 d . . . . .
C30 C 0.14434(11) 0.50814(9) 0.27489(16) 0.0282(4) Uani 1 1 d . . . . .
C31 C 0.18658(11) 0.54652(9) 0.21380(17) 0.0320(5) Uani 1 1 d . . . . .
H31 H 0.1797 0.5452 0.1321 0.038 Uiso 1 1 calc R U . . .
C32 C 0.23967(11) 0.58731(9) 0.27748(18) 0.0345(5) Uani 1 1 d . . . . .
H32 H 0.2697 0.6144 0.2384 0.041 Uiso 1 1 calc R U . . .
C33 C 0.24952(11) 0.58919(9) 0.39696(18) 0.0339(5) Uani 1 1 d . . . . .
H33 H 0.2864 0.6174 0.4379 0.041 Uiso 1 1 calc R U . . .
C34 C 0.20648(11) 0.55068(9) 0.45796(17) 0.0307(5) Uani 1 1 d . . . . .
H34 H 0.2130 0.5520 0.5397 0.037 Uiso 1 1 calc R U . . .
C35 C 0.15366(11) 0.51040(9) 0.39411(16) 0.0264(4) Uani 1 1 d . . . . .
C36 C 0.09946(10) 0.46449(8) 0.42868(16) 0.0248(4) Uani 1 1 d . . . . .
C37 C 0.03522(11) 0.41283(8) 0.55218(16) 0.0258(4) Uani 1 1 d . . . . .
C38 C 0.01569(11) 0.39610(9) 0.66405(16) 0.0283(4) Uani 1 1 d . . . . .
C39 C 0.04710(12) 0.41606(9) 0.77400(17) 0.0334(5) Uani 1 1 d . . . . .
H39 H 0.0872 0.4469 0.7866 0.040 Uiso 1 1 calc R U . . .
C40 C 0.01760(13) 0.38927(10) 0.86468(18) 0.0408(5) Uani 1 1 d . . . . .
H40 H 0.0381 0.4017 0.9413 0.049 Uiso 1 1 calc R U . . .
C41 C -0.04137(13) 0.34450(10) 0.84579(18) 0.0398(5) Uani 1 1 d . . . . .
H41 H -0.0599 0.3266 0.9099 0.048 Uiso 1 1 calc R U . . .
C42 C -0.07390(12) 0.32526(10) 0.73506(17) 0.0353(5) Uani 1 1 d . . . . .
H42 H -0.1151 0.2952 0.7222 0.042 Uiso 1 1 calc R U . . .
C43 C -0.04378(11) 0.35161(9) 0.64461(16) 0.0291(4) Uani 1 1 d . . . . .
C44 C -0.06197(11) 0.34067(9) 0.51917(16) 0.0285(4) Uani 1 1 d . . . . .
C45 C 0.07142(11) 0.31833(9) 0.33655(16) 0.0269(4) Uani 1 1 d . . . . .
C46 C 0.09553(12) 0.28023(10) 0.43048(17) 0.0354(5) Uani 1 1 d . . . . .
H46 H 0.0744 0.2871 0.4995 0.042 Uiso 1 1 calc R U . . .
C47 C 0.14928(13) 0.23273(10) 0.42649(18) 0.0419(5) Uani 1 1 d . . . . .
H47 H 0.1633 0.2075 0.4918 0.050 Uiso 1 1 calc R U . . .
C48 C 0.18231(12) 0.22195(10) 0.32905(18) 0.0372(5) Uani 1 1 d . . . . .
H48 H 0.2197 0.1899 0.3268 0.045 Uiso 1 1 calc R U . . .
C49 C 0.16032(12) 0.25842(9) 0.23461(18) 0.0343(5) Uani 1 1 d . . . . .
H49 H 0.1829 0.2516 0.1667 0.041 Uiso 1 1 calc R U . . .
C50 C 0.10533(11) 0.30514(9) 0.23813(17) 0.0320(5) Uani 1 1 d . . . . .
H50 H 0.0901 0.3291 0.1712 0.038 Uiso 1 1 calc R U . . .
C51 C -0.07277(11) 0.37638(9) 0.24810(16) 0.0260(4) Uani 1 1 d . . . . .
C52 C -0.12831(11) 0.42401(9) 0.24791(16) 0.0288(4) Uani 1 1 d . . . . .
H52 H -0.1171 0.4542 0.3053 0.035 Uiso 1 1 calc R U . . .
C53 C -0.19887(11) 0.42815(9) 0.16655(17) 0.0326(5) Uani 1 1 d . . . . .
H53 H -0.2351 0.4610 0.1683 0.039 Uiso 1 1 calc R U . . .
C54 C -0.21679(11) 0.38435(9) 0.08256(17) 0.0311(5) Uani 1 1 d . . . . .
H54 H -0.2649 0.3873 0.0262 0.037 Uiso 1 1 calc R U . . .
C55 C -0.16426(11) 0.33645(9) 0.08131(16) 0.0294(4) Uani 1 1 d . . . . .
H55 H -0.1766 0.3060 0.0247 0.035 Uiso 1 1 calc R U . . .
C56 C -0.09338(11) 0.33278(9) 0.16272(16) 0.0266(4) Uani 1 1 d . . . . .
H56 H -0.0577 0.2996 0.1604 0.032 Uiso 1 1 calc R U . . .
N1 N 0.51568(10) 0.45713(7) 0.60650(13) 0.0317(4) Uani 1 1 d . . . . .
H1N H 0.5272 0.4795 0.5542 0.048 Uiso 1 1 calc R U . . .
N2 N 0.54757(9) 0.44493(7) 0.80912(13) 0.0247(3) Uani 1 1 d . . . . .
N3 N 0.59914(9) 0.46239(7) 1.00821(13) 0.0251(3) Uani 1 1 d . . . . .
N4 N 0.50576(9) 0.38142(7) 0.95729(13) 0.0238(3) Uani 1 1 d . . . . .
N5 N 0.41814(10) 0.29623(7) 0.97623(14) 0.0340(4) Uani 1 1 d . . . . .
H5N H 0.4111 0.2981 0.9040 0.051 Uiso 1 1 calc R U . . .
N6 N 0.05512(10) 0.44700(8) 0.13251(14) 0.0375(4) Uani 1 1 d . . . . .
H6N H 0.0764 0.4686 0.0871 0.056 Uiso 1 1 calc R U . . .
N7 N 0.06047(9) 0.43542(7) 0.33583(13) 0.0264(4) Uani 1 1 d . . . . .
N8 N 0.09071(9) 0.45462(7) 0.53782(13) 0.0264(4) Uani 1 1 d . . . . .
N9 N -0.00948(9) 0.38010(7) 0.46862(13) 0.0263(4) Uani 1 1 d . . . . .
N10 N -0.11299(11) 0.30334(8) 0.46766(16) 0.0364(4) Uani 1 1 d . . . . .
H10N H -0.1125(15) 0.3041(11) 0.392(2) 0.058(8) 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
B1 N4 1.582(2) . ?
B1 N2 1.597(3) . ?
B1 C17 1.619(3) . ?
B1 C23 1.623(3) . ?
B2 N9 1.578(3) . ?
B2 N7 1.593(3) . ?
B2 C51 1.619(3) . ?
B2 C45 1.626(3) . ?
C1 N1 1.260(2) . ?
C1 N2 1.435(2) . ?
C1 C2 1.474(3) . ?
C2 C3 1.384(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.464(3) . ?
C8 N3 1.335(2) . ?
C8 N2 1.341(2) . ?
C9 N3 1.338(2) . ?
C9 N4 1.341(2) . ?
C9 C10 1.459(3) . ?
C10 C11 1.389(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.478(3) . ?
C16 N5 1.264(2) . ?
C16 N4 1.438(2) . ?
C17 C22 1.396(3) . ?
C17 C18 1.406(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.399(3) . ?
C23 C24 1.400(3) . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 N6 1.261(2) . ?
C29 N7 1.429(2) . ?
C29 C30 1.471(3) . ?
C30 C35 1.386(3) . ?
C30 C31 1.382(3) . ?
C31 C32 1.393(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.389(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.464(3) . ?
C36 N8 1.335(2) . ?
C36 N7 1.340(2) . ?
C37 N8 1.340(2) . ?
C37 N9 1.343(2) . ?
C37 C38 1.456(3) . ?
C38 C39 1.385(3) . ?
C38 C43 1.390(3) . ?
C39 C40 1.382(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.389(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.392(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.381(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.477(3) . ?
C44 N10 1.266(3) . ?
C44 N9 1.435(2) . ?
C45 C46 1.398(3) . ?
C45 C50 1.401(3) . ?
C46 C47 1.390(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.373(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.376(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.390(3) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C56 1.399(3) . ?
C51 C52 1.406(3) . ?
C52 C53 1.384(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.386(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.380(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.387(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
N1 H1N 0.8400 . ?
N5 H5N 0.8400 . ?
N6 H6N 0.8400 . ?
N10 H10N 0.89(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 B1 N2 100.07(14) . . ?
N4 B1 C17 109.75(15) . . ?
N2 B1 C17 107.71(15) . . ?
N4 B1 C23 111.05(15) . . ?
N2 B1 C23 110.50(15) . . ?
C17 B1 C23 116.46(16) . . ?
N9 B2 N7 100.21(15) . . ?
N9 B2 C51 110.82(15) . . ?
N7 B2 C51 109.82(16) . . ?
N9 B2 C45 109.12(16) . . ?
N7 B2 C45 108.85(15) . . ?
C51 B2 C45 116.73(16) . . ?
N1 C1 N2 122.96(17) . . ?
N1 C1 C2 130.60(18) . . ?
N2 C1 C2 106.43(15) . . ?
C3 C2 C7 121.05(18) . . ?
C3 C2 C1 131.48(18) . . ?
C7 C2 C1 107.44(16) . . ?
C2 C3 C4 117.46(19) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.43(19) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 121.42(19) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 116.76(19) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
C2 C7 C6 121.87(18) . . ?
C2 C7 C8 107.01(16) . . ?
C6 C7 C8 131.08(18) . . ?
N3 C8 N2 126.27(17) . . ?
N3 C8 C7 123.72(16) . . ?
N2 C8 C7 110.01(16) . . ?
N3 C9 N4 126.12(17) . . ?
N3 C9 C10 123.79(16) . . ?
N4 C9 C10 110.08(16) . . ?
C11 C10 C15 121.43(18) . . ?
C11 C10 C9 131.47(18) . . ?
C15 C10 C9 107.10(16) . . ?
C10 C11 C12 117.26(19) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 C13 121.09(19) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 121.25(19) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 117.56(19) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 C10 121.40(18) . . ?
C14 C15 C16 130.97(18) . . ?
C10 C15 C16 107.62(16) . . ?
N5 C16 N4 127.52(17) . . ?
N5 C16 C15 126.44(17) . . ?
N4 C16 C15 106.03(15) . . ?
C22 C17 C18 115.39(17) . . ?
C22 C17 B1 122.71(17) . . ?
C18 C17 B1 121.82(17) . . ?
C19 C18 C17 122.39(18) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C20 C19 C18 120.55(18) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.15(19) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C22 119.95(19) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 122.55(18) . . ?
C17 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C28 C23 C24 116.32(17) . . ?
C28 C23 B1 120.42(17) . . ?
C24 C23 B1 123.23(16) . . ?
C25 C24 C23 122.21(18) . . ?
C25 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C26 C25 C24 120.05(19) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.51(18) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C28 119.88(18) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C23 122.01(18) . . ?
C27 C28 H28 119.0 . . ?
C23 C28 H28 119.0 . . ?
N6 C29 N7 125.62(18) . . ?
N6 C29 C30 127.66(18) . . ?
N7 C29 C30 106.71(15) . . ?
C35 C30 C31 121.62(18) . . ?
C35 C30 C29 107.57(16) . . ?
C31 C30 C29 130.79(18) . . ?
C30 C31 C32 117.00(19) . . ?
C30 C31 H31 121.5 . . ?
C32 C31 H31 121.5 . . ?
C33 C32 C31 121.35(19) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C32 C33 C34 121.40(19) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C35 C34 C33 116.93(19) . . ?
C35 C34 H34 121.5 . . ?
C33 C34 H34 121.5 . . ?
C30 C35 C34 121.69(18) . . ?
C30 C35 C36 106.67(16) . . ?
C34 C35 C36 131.64(18) . . ?
N8 C36 N7 126.12(17) . . ?
N8 C36 C35 123.64(17) . . ?
N7 C36 C35 110.24(16) . . ?
N8 C37 N9 126.26(17) . . ?
N8 C37 C38 123.65(17) . . ?
N9 C37 C38 110.09(17) . . ?
C39 C38 C43 121.87(18) . . ?
C39 C38 C37 131.05(19) . . ?
C43 C38 C37 107.07(17) . . ?
C38 C39 C40 117.2(2) . . ?
C38 C39 H39 121.4 . . ?
C40 C39 H39 121.4 . . ?
C39 C40 C41 121.2(2) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 H40 119.4 . . ?
C40 C41 C42 121.5(2) . . ?
C40 C41 H41 119.2 . . ?
C42 C41 H41 119.2 . . ?
C43 C42 C41 117.2(2) . . ?
C43 C42 H42 121.4 . . ?
C41 C42 H42 121.4 . . ?
C42 C43 C38 121.02(19) . . ?
C42 C43 C44 131.37(19) . . ?
C38 C43 C44 107.60(16) . . ?
N10 C44 N9 127.39(18) . . ?
N10 C44 C43 126.51(18) . . ?
N9 C44 C43 106.09(16) . . ?
C46 C45 C50 115.16(18) . . ?
C46 C45 B2 122.31(17) . . ?
C50 C45 B2 122.51(17) . . ?
C45 C46 C47 122.40(19) . . ?
C45 C46 H46 118.8 . . ?
C47 C46 H46 118.8 . . ?
C48 C47 C46 120.6(2) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C47 C48 C49 118.9(2) . . ?
C47 C48 H48 120.6 . . ?
C49 C48 H48 120.6 . . ?
C48 C49 C50 120.33(19) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C49 C50 C45 122.58(19) . . ?
C49 C50 H50 118.7 . . ?
C45 C50 H50 118.7 . . ?
C56 C51 C52 116.35(17) . . ?
C56 C51 B2 123.76(17) . . ?
C52 C51 B2 119.88(17) . . ?
C53 C52 C51 121.88(18) . . ?
C53 C52 H52 119.1 . . ?
C51 C52 H52 119.1 . . ?
C52 C53 C54 120.06(19) . . ?
C52 C53 H53 120.0 . . ?
C54 C53 H53 120.0 . . ?
C55 C54 C53 119.59(18) . . ?
C55 C54 H54 120.2 . . ?
C53 C54 H54 120.2 . . ?
C54 C55 C56 120.03(18) . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C55 C56 C51 122.07(18) . . ?
C55 C56 H56 119.0 . . ?
C51 C56 H56 119.0 . . ?
C1 N1 H1N 109.5 . . ?
C8 N2 C1 109.03(15) . . ?
C8 N2 B1 123.27(15) . . ?
C1 N2 B1 126.39(15) . . ?
C8 N3 C9 115.22(15) . . ?
C9 N4 C16 109.16(15) . . ?
C9 N4 B1 123.90(15) . . ?
C16 N4 B1 125.69(15) . . ?
C16 N5 H5N 109.5 . . ?
C29 N6 H6N 109.5 . . ?
C36 N7 C29 108.74(16) . . ?
C36 N7 B2 123.60(16) . . ?
C29 N7 B2 126.80(15) . . ?
C36 N8 C37 115.10(16) . . ?
C37 N9 C44 109.13(15) . . ?
C37 N9 B2 123.50(15) . . ?
C44 N9 B2 125.61(15) . . ?
C44 N10 H10N 110.3(16) . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1446084'
_audit_update_record             
;
2016-04-22 deposited with the CCDC.
2016-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H21 B Cl2 N4 O'
_chemical_formula_weight         523.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8161(5)
_cell_length_b                   10.6099(6)
_cell_length_c                   13.5285(8)
_cell_angle_alpha                78.972(2)
_cell_angle_beta                 86.357(3)
_cell_angle_gamma                84.524(3)
_cell_volume                     1235.06(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7749
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.98

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    0.295
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5257
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14690
_diffrn_reflns_av_unetI/netI     0.5272
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.535
_diffrn_reflns_theta_max         26.167
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             4687
_reflns_number_gt                3168
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4687
_refine_ls_number_parameters     374
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1833
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1401
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.0545(3) 0.2302(2) 0.77358(19) 0.0199(6) Uani 1 1 d . . . . .
C1 C 0.2457(2) 0.2641(2) 0.91127(17) 0.0205(5) Uani 1 1 d . . . . .
C2 C 0.3130(2) 0.1811(2) 1.00064(17) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.4024(2) 0.2077(2) 1.07299(17) 0.0235(5) Uani 1 1 d . . . . .
H3 H 0.4317 0.2921 1.0705 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4485(2) 0.1059(2) 1.15018(18) 0.0282(6) Uani 1 1 d . . . . .
H4 H 0.5099 0.1215 1.2010 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4056(2) -0.0180(2) 1.15362(18) 0.0254(5) Uani 1 1 d . . . . .
H5 H 0.4382 -0.0852 1.2069 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3161(2) -0.0451(2) 1.08061(17) 0.0221(5) Uani 1 1 d . . . . .
H6 H 0.2883 -0.1298 1.0822 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2690(2) 0.0574(2) 1.00489(16) 0.0191(5) Uani 1 1 d . . . . .
C8 C 0.1735(2) 0.06307(19) 0.91997(16) 0.0181(5) Uani 1 1 d . . . . .
C9 C 0.0386(2) -0.01691(19) 0.81471(16) 0.0187(5) Uani 1 1 d . . . . .
C10 C -0.0261(2) -0.1199(2) 0.77544(17) 0.0204(5) Uani 1 1 d . . . . .
C11 C -0.0329(2) -0.2491(2) 0.81441(17) 0.0239(5) Uani 1 1 d . . . . .
H11 H 0.0095 -0.2878 0.8770 0.029 Uiso 1 1 calc R U . . .
C12 C -0.1050(3) -0.3206(2) 0.75756(18) 0.0284(6) Uani 1 1 d . . . . .
H12 H -0.1138 -0.4097 0.7825 0.034 Uiso 1 1 calc R U . . .
C13 C -0.1639(3) -0.2641(2) 0.66566(18) 0.0300(6) Uani 1 1 d . . . . .
H13 H -0.2116 -0.3157 0.6287 0.036 Uiso 1 1 calc R U . . .
C14 C -0.1553(3) -0.1332(2) 0.62555(18) 0.0280(6) Uani 1 1 d . . . . .
H14 H -0.1949 -0.0948 0.5621 0.034 Uiso 1 1 calc R U . . .
C15 C -0.0859(2) -0.0627(2) 0.68343(17) 0.0214(5) Uani 1 1 d . . . . .
C16 C -0.0571(3) 0.0759(2) 0.66439(17) 0.0235(5) Uani 1 1 d . . . . .
C17 C -0.1004(2) 0.30764(19) 0.80910(16) 0.0196(5) Uani 1 1 d . . . . .
C18 C -0.1196(2) 0.34084(19) 0.90529(17) 0.0223(5) Uani 1 1 d . . . . .
H18 H -0.0373 0.3215 0.9492 0.027 Uiso 1 1 calc R U . . .
C19 C -0.2555(3) 0.4011(2) 0.93793(18) 0.0269(6) Uani 1 1 d . . . . .
H19 H -0.2642 0.4232 1.0030 0.032 Uiso 1 1 calc R U . . .
C20 C -0.3771(3) 0.4288(2) 0.87660(19) 0.0270(6) Uani 1 1 d . . . . .
H20 H -0.4705 0.4686 0.8994 0.032 Uiso 1 1 calc R U . . .
C21 C -0.3627(3) 0.3984(2) 0.78136(19) 0.0281(6) Uani 1 1 d . . . . .
H21 H -0.4463 0.4172 0.7384 0.034 Uiso 1 1 calc R U . . .
C22 C -0.2251(2) 0.34005(19) 0.74846(17) 0.0243(5) Uani 1 1 d . . . . .
H22 H -0.2162 0.3218 0.6822 0.029 Uiso 1 1 calc R U . . .
C23 C 0.1540(2) 0.3044(2) 0.67888(16) 0.0234(5) Uani 1 1 d . . . . .
C24 C 0.1099(3) 0.4255(2) 0.62350(18) 0.0318(6) Uani 1 1 d . . . . .
H24 H 0.0171 0.4699 0.6422 0.038 Uiso 1 1 calc R U . . .
C25 C 0.1984(3) 0.4833(3) 0.54126(19) 0.0421(7) Uani 1 1 d . . . . .
H25 H 0.1650 0.5657 0.5045 0.050 Uiso 1 1 calc R U . . .
C26 C 0.3321(3) 0.4221(3) 0.5135(2) 0.0501(9) Uani 1 1 d . . . . .
H26 H 0.3921 0.4615 0.4573 0.060 Uiso 1 1 calc R U . . .
C27 C 0.3811(3) 0.3018(3) 0.5675(2) 0.0487(8) Uani 1 1 d . . . . .
H27 H 0.4750 0.2590 0.5486 0.058 Uiso 1 1 calc R U . . .
C28 C 0.2927(3) 0.2441(2) 0.64911(19) 0.0355(6) Uani 1 1 d . . . . .
H28 H 0.3271 0.1618 0.6856 0.043 Uiso 1 1 calc R U . . .
Cl1 Cl 0.3542(3) 0.6612(3) 0.7230(2) 0.0340(5) Uani 0.6 1 d . . P A 1
Cl2 Cl 0.3259(4) 0.9255(3) 0.6071(3) 0.0373(5) Uani 0.6 1 d . . P A 1
Cl3 Cl 0.3624(8) 0.9122(7) 0.5944(6) 0.097(2) Uani 0.4 1 d . . P A 2
Cl4 Cl 0.3708(8) 0.6661(6) 0.7155(6) 0.111(2) Uani 0.4 1 d . . P A 2
N1 N 0.2557(8) 0.3819(7) 0.8810(5) 0.0145(11) Uani 0.7 1 d . . P B 1
N2 N 0.16053(19) 0.18303(16) 0.86568(13) 0.0196(4) Uani 1 1 d . . . . .
N3 N 0.11057(19) -0.03909(16) 0.90008(13) 0.0195(4) Uani 1 1 d . . . . .
N4 N 0.01575(19) 0.09581(15) 0.75055(13) 0.0186(4) Uani 1 1 d . . . . .
O1 O -0.0791(5) 0.1577(4) 0.5869(4) 0.0290(9) Uani 0.7 1 d . . P C 1
N5 N -0.1156(14) 0.1605(14) 0.5997(12) 0.020(3) Uani 0.3 1 d . U P C 2
H5A H -0.1620 0.1265 0.5606 0.030 Uiso 0.3 1 calc R U P C 2
O2 O 0.262(3) 0.385(2) 0.8826(18) 0.064(4) Uani 0.3 1 d . U P B 2
H1N H 0.204(3) 0.410(3) 0.821(2) 0.006(7) Uiso 0.7 1 d . . P D 1
C29 C 0.2754(3) 0.7662(2) 0.61826(19) 0.0335(6) Uani 1 1 d . . . . .
H29A H 0.1629 0.7665 0.6245 0.040 Uiso 1 1 calc R U . A 1
H29B H 0.3108 0.7337 0.5561 0.040 Uiso 1 1 calc R U . 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
B1 N2 1.580(3) . ?
B1 N4 1.588(3) . ?
B1 C17 1.620(3) . ?
B1 C23 1.623(3) . ?
C1 N1 1.248(8) . ?
C1 O2 1.29(2) . ?
C1 N2 1.438(3) . ?
C1 C2 1.474(3) . ?
C2 C3 1.380(3) . ?
C2 C7 1.394(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.395(3) . ?
C7 C8 1.456(3) . ?
C8 N2 1.341(3) . ?
C8 N3 1.342(3) . ?
C9 N3 1.324(3) . ?
C9 N4 1.343(3) . ?
C9 C10 1.477(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.389(3) . ?
C11 C12 1.396(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.487(3) . ?
C16 N5 1.227(16) . ?
C16 O1 1.239(5) . ?
C16 N4 1.425(3) . ?
C17 C22 1.391(3) . ?
C17 C18 1.408(3) . ?
C18 C19 1.390(3) . ?
C19 C20 1.373(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.396(3) . ?
C23 C24 1.391(3) . ?
C23 C28 1.397(3) . ?
C24 C25 1.394(3) . ?
C25 C26 1.358(4) . ?
C26 C27 1.388(4) . ?
C27 C28 1.388(3) . ?
Cl1 C29 1.762(4) . ?
Cl2 C29 1.765(4) . ?
Cl3 C29 1.759(8) . ?
Cl4 C29 1.732(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 B1 N4 100.58(16) . . ?
N2 B1 C17 110.10(17) . . ?
N4 B1 C17 109.52(16) . . ?
N2 B1 C23 109.07(17) . . ?
N4 B1 C23 109.39(16) . . ?
C17 B1 C23 116.93(18) . . ?
N1 C1 N2 125.8(4) . . ?
O2 C1 N2 128.4(11) . . ?
N1 C1 C2 127.9(4) . . ?
O2 C1 C2 125.2(11) . . ?
N2 C1 C2 106.32(18) . . ?
C3 C2 C7 121.1(2) . . ?
C3 C2 C1 131.59(19) . . ?
C7 C2 C1 107.3(2) . . ?
C2 C3 C4 117.7(2) . . ?
C5 C4 C3 121.1(2) . . ?
C6 C5 C4 121.3(2) . . ?
C5 C6 C7 117.1(2) . . ?
C2 C7 C6 121.7(2) . . ?
C2 C7 C8 107.17(19) . . ?
C6 C7 C8 131.2(2) . . ?
N2 C8 N3 126.1(2) . . ?
N2 C8 C7 110.17(18) . . ?
N3 C8 C7 123.7(2) . . ?
N3 C9 N4 127.47(19) . . ?
N3 C9 C10 122.6(2) . . ?
N4 C9 C10 109.9(2) . . ?
C11 C10 C15 122.1(2) . . ?
C11 C10 C9 131.4(2) . . ?
C15 C10 C9 106.51(18) . . ?
C10 C11 C12 116.8(2) . . ?
C13 C12 C11 121.2(2) . . ?
C12 C13 C14 122.0(2) . . ?
C15 C14 C13 116.3(2) . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 C16 130.7(2) . . ?
C10 C15 C16 107.70(19) . . ?
N5 C16 N4 126.0(8) . . ?
O1 C16 N4 125.3(3) . . ?
N5 C16 C15 125.8(8) . . ?
O1 C16 C15 128.2(3) . . ?
N4 C16 C15 106.28(19) . . ?
C22 C17 C18 115.84(19) . . ?
C22 C17 B1 122.14(19) . . ?
C18 C17 B1 121.9(2) . . ?
C19 C18 C17 122.0(2) . . ?
C20 C19 C18 120.3(2) . . ?
C19 C20 C21 119.5(2) . . ?
C20 C21 C22 119.8(2) . . ?
C17 C22 C21 122.5(2) . . ?
C24 C23 C28 116.82(19) . . ?
C24 C23 B1 124.26(19) . . ?
C28 C23 B1 118.9(2) . . ?
C23 C24 C25 121.8(2) . . ?
C26 C25 C24 120.2(3) . . ?
C25 C26 C27 119.9(2) . . ?
C28 C27 C26 119.9(3) . . ?
C27 C28 C23 121.5(3) . . ?
C8 N2 C1 109.00(19) . . ?
C8 N2 B1 125.10(17) . . ?
C1 N2 B1 125.61(17) . . ?
C9 N3 C8 114.60(18) . . ?
C9 N4 C16 109.49(17) . . ?
C9 N4 B1 123.88(18) . . ?
C16 N4 B1 126.49(18) . . ?
Cl4 C29 Cl3 106.7(4) . . ?
Cl1 C29 Cl2 112.7(2) . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1446085'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H20 B Cl2 N3 O2'
_chemical_formula_weight         524.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7931(11)
_cell_length_b                   10.5963(13)
_cell_length_c                   13.5308(18)
_cell_angle_alpha                78.771(5)
_cell_angle_beta                 86.503(6)
_cell_angle_gamma                84.592(6)
_cell_volume                     1229.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8627
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.34

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.298
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16216
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.966
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             4790
_reflns_number_gt                3711
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+1.1006P] 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         4790
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.4452(3) 0.7688(3) 0.22634(19) 0.0208(6) Uani 1 1 d . . . . .
C1 C 0.5586(3) 0.9240(2) 0.33557(17) 0.0235(5) Uani 1 1 d . . . . .
C2 C 0.5869(3) 1.0626(2) 0.31689(17) 0.0226(5) Uani 1 1 d . . . . .
C3 C 0.6562(3) 1.1335(3) 0.37392(19) 0.0280(6) Uani 1 1 d . . . . .
H3 H 0.6963 1.0948 0.4374 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6647(3) 1.2634(3) 0.3347(2) 0.0302(6) Uani 1 1 d . . . . .
H4 H 0.7135 1.3146 0.3715 0.036 Uiso 1 1 calc R U . . .
C5 C 0.6032(3) 1.3212(2) 0.24206(19) 0.0270(6) Uani 1 1 d . . . . .
H5 H 0.6105 1.4108 0.2173 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5320(3) 1.2495(2) 0.18605(18) 0.0248(5) Uani 1 1 d . . . . .
H6 H 0.4891 1.2882 0.1235 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5260(3) 1.1195(2) 0.22467(17) 0.0210(5) Uani 1 1 d . . . . .
C8 C 0.4612(3) 1.0175(2) 0.18563(17) 0.0190(5) Uani 1 1 d . . . . .
C9 C 0.3261(3) 0.9371(2) 0.08012(17) 0.0203(5) Uani 1 1 d . . . . .
C10 C 0.2302(3) 0.9427(2) -0.00569(17) 0.0202(5) Uani 1 1 d . . . . .
C11 C 0.1831(3) 1.0452(2) -0.08057(17) 0.0236(5) Uani 1 1 d . . . . .
H11 H 0.2104 1.1301 -0.0816 0.028 Uiso 1 1 calc R U . . .
C12 C 0.0940(3) 1.0185(3) -0.15431(18) 0.0258(5) Uani 1 1 d . . . . .
H12 H 0.0616 1.0861 -0.2078 0.031 Uiso 1 1 calc R U . . .
C13 C 0.0514(3) 0.8941(3) -0.15080(19) 0.0282(6) Uani 1 1 d . . . . .
H13 H -0.0103 0.8787 -0.2018 0.034 Uiso 1 1 calc R U . . .
C14 C 0.0974(3) 0.7918(3) -0.07415(18) 0.0250(5) Uani 1 1 d . . . . .
H14 H 0.0688 0.7070 -0.0719 0.030 Uiso 1 1 calc R U . . .
C15 C 0.1869(3) 0.8193(2) -0.00139(17) 0.0216(5) Uani 1 1 d . . . . .
C16 C 0.2544(3) 0.7358(2) 0.08833(17) 0.0209(5) Uani 1 1 d . . . . .
C17 C 0.3457(3) 0.6956(2) 0.32105(17) 0.0231(5) Uani 1 1 d . . . . .
C18 C 0.3892(3) 0.5746(2) 0.37669(18) 0.0290(6) Uani 1 1 d . . . . .
H18 H 0.4816 0.5296 0.3577 0.035 Uiso 1 1 calc R U . . .
C19 C 0.3016(4) 0.5170(3) 0.45954(19) 0.0394(7) Uani 1 1 d . . . . .
H19 H 0.3352 0.4345 0.4968 0.047 Uiso 1 1 calc R U . . .
C20 C 0.1663(4) 0.5796(3) 0.4872(2) 0.0454(9) Uani 1 1 d . . . . .
H20 H 0.1064 0.5408 0.5438 0.054 Uiso 1 1 calc R U . . .
C21 C 0.1178(3) 0.6996(4) 0.4324(2) 0.0457(8) Uani 1 1 d . . . . .
H21 H 0.0238 0.7429 0.4506 0.055 Uiso 1 1 calc R U . . .
C22 C 0.2069(3) 0.7560(3) 0.3508(2) 0.0333(6) Uani 1 1 d . . . . .
H22 H 0.1727 0.8385 0.3139 0.040 Uiso 1 1 calc R U . . .
C23 C 0.6007(3) 0.6917(2) 0.19044(17) 0.0207(5) Uani 1 1 d . . . . .
C24 C 0.6204(3) 0.6586(2) 0.09451(18) 0.0235(5) Uani 1 1 d . . . . .
H24 H 0.5378 0.6782 0.0504 0.028 Uiso 1 1 calc R U . . .
C25 C 0.7560(3) 0.5982(2) 0.06163(19) 0.0274(6) Uani 1 1 d . . . . .
H25 H 0.7641 0.5760 -0.0033 0.033 Uiso 1 1 calc R U . . .
C26 C 0.8790(3) 0.5705(2) 0.12332(19) 0.0272(6) Uani 1 1 d . . . . .
H26 H 0.9724 0.5305 0.1008 0.033 Uiso 1 1 calc R U . . .
C27 C 0.8646(3) 0.6018(2) 0.21844(19) 0.0283(6) Uani 1 1 d . . . . .
H27 H 0.9490 0.5839 0.2611 0.034 Uiso 1 1 calc R U . . .
C28 C 0.7274(3) 0.6591(2) 0.25177(18) 0.0250(5) Uani 1 1 d . . . . .
H28 H 0.7189 0.6769 0.3181 0.030 Uiso 1 1 calc R U . . .
C29 C 0.2252(3) 0.2344(3) 0.3820(2) 0.0321(6) Uani 1 1 d . . . . .
H29A H 0.3380 0.2311 0.3728 0.038 Uiso 1 1 calc R U . . .
H29B H 0.1955 0.2687 0.4441 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.14255(11) 0.33790(7) 0.27832(7) 0.0536(3) Uani 1 1 d . . . . .
Cl2 Cl 0.16684(12) 0.07834(7) 0.39579(6) 0.0563(3) Uani 1 1 d . . . . .
N1 N 0.4844(2) 0.90377(18) 0.24925(14) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.3884(2) 1.03884(19) 0.10012(14) 0.0204(4) Uani 1 1 d . . . . .
N3 N 0.3388(2) 0.81683(19) 0.13384(14) 0.0202(4) Uani 1 1 d . . . . .
O2 O 0.2441(2) 0.61820(19) 0.11881(15) 0.0376(5) Uani 1 1 d . . . . .
O1 O 0.5918(2) 0.84084(18) 0.40873(14) 0.0376(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 N3 1.583(3) . ?
B1 N1 1.594(3) . ?
B1 C17 1.617(3) . ?
B1 C23 1.624(4) . ?
C1 O1 1.220(3) . ?
C1 N1 1.433(3) . ?
C1 C2 1.483(3) . ?
C2 C3 1.378(4) . ?
C2 C7 1.391(3) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.465(3) . ?
C8 N2 1.327(3) . ?
C8 N1 1.344(3) . ?
C9 N2 1.333(3) . ?
C9 N3 1.337(3) . ?
C9 C10 1.465(3) . ?
C10 C11 1.384(3) . ?
C10 C15 1.385(3) . ?
C11 C12 1.392(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.477(3) . ?
C16 O2 1.244(3) . ?
C16 N3 1.432(3) . ?
C17 C18 1.387(3) . ?
C17 C22 1.398(4) . ?
C18 C19 1.393(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.406(3) . ?
C23 C28 1.406(3) . ?
C24 C25 1.390(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 Cl2 1.749(3) . ?
C29 Cl1 1.754(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?

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
N3 B1 N1 100.38(17) . . ?
N3 B1 C17 109.3(2) . . ?
N1 B1 C17 108.95(19) . . ?
N3 B1 C23 109.92(19) . . ?
N1 B1 C23 109.36(19) . . ?
C17 B1 C23 117.6(2) . . ?
O1 C1 N1 125.3(2) . . ?
O1 C1 C2 128.0(2) . . ?
N1 C1 C2 106.65(19) . . ?
C3 C2 C7 121.5(2) . . ?
C3 C2 C1 131.2(2) . . ?
C7 C2 C1 107.2(2) . . ?
C2 C3 C4 117.1(2) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 117.3(2) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C6 C7 C2 121.6(2) . . ?
C6 C7 C8 131.4(2) . . ?
C2 C7 C8 107.0(2) . . ?
N2 C8 N1 126.5(2) . . ?
N2 C8 C7 123.3(2) . . ?
N1 C8 C7 110.3(2) . . ?
N2 C9 N3 126.4(2) . . ?
N2 C9 C10 123.9(2) . . ?
N3 C9 C10 109.7(2) . . ?
C11 C10 C15 122.0(2) . . ?
C11 C10 C9 130.8(2) . . ?
C15 C10 C9 107.2(2) . . ?
C10 C11 C12 117.1(2) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 C13 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 117.0(2) . . ?
C15 C14 H14 121.5 . . ?
C13 C14 H14 121.5 . . ?
C10 C15 C14 121.3(2) . . ?
C10 C15 C16 107.5(2) . . ?
C14 C15 C16 131.2(2) . . ?
O2 C16 N3 125.9(2) . . ?
O2 C16 C15 128.0(2) . . ?
N3 C16 C15 106.14(19) . . ?
C18 C17 C22 116.6(2) . . ?
C18 C17 B1 124.1(2) . . ?
C22 C17 B1 119.3(2) . . ?
C17 C18 C19 122.0(3) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 119.7(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C17 122.1(3) . . ?
C21 C22 H22 118.9 . . ?
C17 C22 H22 118.9 . . ?
C24 C23 C28 115.6(2) . . ?
C24 C23 B1 122.3(2) . . ?
C28 C23 B1 122.0(2) . . ?
C25 C24 C23 122.6(2) . . ?
C25 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C26 C25 C24 120.0(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 119.3(2) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 122.1(2) . . ?
C27 C28 H28 118.9 . . ?
C23 C28 H28 118.9 . . ?
Cl2 C29 Cl1 111.32(16) . . ?
Cl2 C29 H29A 109.4 . . ?
Cl1 C29 H29A 109.4 . . ?
Cl2 C29 H29B 109.4 . . ?
Cl1 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C8 N1 C1 108.81(19) . . ?
C8 N1 B1 124.37(19) . . ?
C1 N1 B1 126.70(19) . . ?
C8 N2 C9 115.2(2) . . ?
C9 N3 C16 109.51(19) . . ?
C9 N3 B1 124.9(2) . . ?
C16 N3 B1 125.25(19) . . ?

_refine_diff_density_max         1.033
_refine_diff_density_min         -0.910
_refine_diff_density_rms         0.068

