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

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

data_LHR315F
_database_code_depnum_ccdc_archive 'CCDC 1823584'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H21 B10 N'
_chemical_formula_weight         311.42

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           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                   7.8295(7)
_cell_length_b                   25.776(2)
_cell_length_c                   11.1821(11)
_cell_angle_alpha                90
_cell_angle_beta                 128.014(3)
_cell_angle_gamma                90
_cell_volume                     1778.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    182
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.058
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6541
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29683
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         25.247
_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             3225
_reflns_number_gt                2266
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1165P)²+1.9488P] 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         3225
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0890
_refine_ls_wR_factor_ref         0.2559
_refine_ls_wR_factor_gt          0.2349
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4425(4) 0.13775(10) 0.4699(3) 0.0450(7) Uani 1 1 d . . . . .
C1 C 0.0549(5) 0.14416(12) 0.2563(4) 0.0424(8) Uani 1 1 d . . . . .
C2 C -0.0556(6) 0.17119(15) 0.3291(4) 0.0565(10) Uani 1 1 d . . . . .
C11 C 0.0872(8) 0.18056(19) 0.4984(5) 0.0829(14) Uani 1 1 d . . . . .
H11A H 0.0031 0.1962 0.5247 0.124 Uiso 1 1 calc R U . . .
H11B H 0.1451 0.1481 0.5509 0.124 Uiso 1 1 calc R U . . .
H11C H 0.2041 0.2033 0.5271 0.124 Uiso 1 1 calc R U . . .
C12 C 0.2712(5) 0.11859(12) 0.3429(4) 0.0397(8) Uani 1 1 d . . . . .
C13 C 0.2602(5) 0.07254(12) 0.2687(3) 0.0413(8) Uani 1 1 d . . . . .
C14 C 0.0385(6) 0.06019(14) 0.1224(4) 0.0529(9) Uani 1 1 d . . . . .
H14A H -0.0104 0.0264 0.1281 0.063 Uiso 1 1 calc R U . . .
H14B H 0.0418 0.0605 0.0371 0.063 Uiso 1 1 calc R U . . .
C15 C 0.4464(5) 0.04391(12) 0.3359(4) 0.0420(8) Uani 1 1 d . . . . .
C16 C 0.4462(7) -0.00505(15) 0.2623(5) 0.0628(11) Uani 1 1 d . . . . .
H16A H 0.5888 -0.0200 0.3242 0.094 Uiso 1 1 calc R U . . .
H16B H 0.3449 -0.0293 0.2521 0.094 Uiso 1 1 calc R U . . .
H16C H 0.4050 0.0029 0.1638 0.094 Uiso 1 1 calc R U . . .
C17 C 0.6373(5) 0.06234(13) 0.4765(4) 0.0425(8) Uani 1 1 d . . . . .
C18 C 0.8375(6) 0.03593(15) 0.5586(4) 0.0548(10) Uani 1 1 d . . . . .
H18A H 0.8483 0.0052 0.5202 0.066 Uiso 1 1 calc R U . . .
C19 C 1.0157(6) 0.05482(17) 0.6935(5) 0.0665(11) Uani 1 1 d . . . . .
H19A H 1.1456 0.0366 0.7457 0.080 Uiso 1 1 calc R U . . .
C20 C 1.0059(6) 0.10088(18) 0.7541(5) 0.0669(11) Uani 1 1 d . . . . .
H20A H 1.1281 0.1133 0.8463 0.080 Uiso 1 1 calc R U . . .
C21 C 0.8149(6) 0.12773(15) 0.6770(4) 0.0579(10) Uani 1 1 d . . . . .
H21A H 0.8084 0.1587 0.7167 0.070 Uiso 1 1 calc R U . . .
C22 C 0.6279(5) 0.10906(13) 0.5382(4) 0.0428(8) Uani 1 1 d . . . . .
B3 B -0.1218(7) 0.10788(16) 0.2625(5) 0.0528(11) Uani 1 1 d . . . . .
H3 H -0.0769 0.0743 0.3373 0.063 Uiso 1 1 calc R U . . .
B4 B -0.1160(6) 0.10468(17) 0.1051(4) 0.0496(10) Uani 1 1 d . . . . .
B5 B -0.0500(7) 0.16814(17) 0.0822(4) 0.0494(10) Uani 1 1 d . . . . .
H5 H 0.0414 0.1738 0.0382 0.059 Uiso 1 1 calc R U . . .
B6 B -0.0048(8) 0.20878(17) 0.2264(5) 0.0553(11) Uani 1 1 d . . . . .
H6 H 0.1157 0.2402 0.2769 0.066 Uiso 1 1 calc R U . . .
B7 B -0.3241(8) 0.15151(19) 0.2214(6) 0.0670(14) Uani 1 1 d . . . . .
H7 H -0.4134 0.1465 0.2672 0.080 Uiso 1 1 calc R U . . .
B8 B -0.3662(8) 0.10970(19) 0.0768(6) 0.0688(14) Uani 1 1 d . . . . .
H8 H -0.4827 0.0774 0.0286 0.083 Uiso 1 1 calc R U . . .
B9 B -0.3240(7) 0.14730(18) -0.0367(5) 0.0631(13) Uani 1 1 d . . . . .
H9 H -0.4140 0.1395 -0.1585 0.076 Uiso 1 1 calc R U . . .
B10 B -0.2525(7) 0.21165(18) 0.0395(5) 0.0594(12) Uani 1 1 d . . . . .
H10 H -0.2969 0.2457 -0.0338 0.071 Uiso 1 1 calc R U . . .
B11 B -0.2506(7) 0.21375(18) 0.1992(6) 0.0608(12) Uani 1 1 d . . . . .
H11 H -0.2924 0.2492 0.2309 0.073 Uiso 1 1 calc R U . . .
B12 B -0.4477(8) 0.17576(19) 0.0372(6) 0.0701(14) Uani 1 1 d . . . . .
H12 H -0.6202 0.1866 -0.0381 0.084 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.309(4) . ?
N1 C22 1.368(4) . ?
C1 C12 1.490(4) . ?
C1 C2 1.663(5) . ?
C1 B5 1.696(5) . ?
C1 B4 1.702(5) . ?
C1 B6 1.707(5) . ?
C1 B3 1.706(5) . ?
C2 C11 1.512(6) . ?
C2 B11 1.707(6) . ?
C2 B6 1.725(6) . ?
C2 B7 1.734(6) . ?
C2 B3 1.735(6) . ?
C12 C13 1.420(4) . ?
C13 C15 1.373(4) . ?
C13 C14 1.514(5) . ?
C14 B4 1.590(6) . ?
C15 C17 1.427(5) . ?
C15 C16 1.506(5) . ?
C17 C18 1.411(5) . ?
C17 C22 1.412(5) . ?
C18 C19 1.366(6) . ?
C19 C20 1.393(6) . ?
C20 C21 1.367(5) . ?
C21 C22 1.409(5) . ?
B3 B8 1.755(7) . ?
B3 B7 1.757(6) . ?
B3 B4 1.791(6) . ?
B4 B5 1.780(6) . ?
B4 B8 1.786(6) . ?
B4 B9 1.787(6) . ?
B5 B10 1.751(6) . ?
B5 B6 1.767(6) . ?
B5 B9 1.773(6) . ?
B6 B11 1.758(6) . ?
B6 B10 1.773(6) . ?
B7 B12 1.765(7) . ?
B7 B11 1.773(6) . ?
B7 B8 1.796(8) . ?
B8 B12 1.776(7) . ?
B8 B9 1.782(7) . ?
B9 B12 1.773(8) . ?
B9 B10 1.790(7) . ?
B10 B12 1.773(7) . ?
B10 B11 1.777(7) . ?
B11 B12 1.783(8) . ?

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
C12 N1 C22 115.3(3) . . ?
C12 C1 C2 126.4(3) . . ?
C12 C1 B5 117.4(3) . . ?
C2 C1 B5 112.3(3) . . ?
C12 C1 B4 105.3(3) . . ?
C2 C1 B4 114.1(3) . . ?
B5 C1 B4 63.2(2) . . ?
C12 C1 B6 128.6(3) . . ?
C2 C1 B6 61.6(2) . . ?
B5 C1 B6 62.6(2) . . ?
B4 C1 B6 115.9(3) . . ?
C12 C1 B3 110.9(3) . . ?
C2 C1 B3 62.0(2) . . ?
B5 C1 B3 114.5(3) . . ?
B4 C1 B3 63.4(2) . . ?
B6 C1 B3 114.3(3) . . ?
C11 C2 C1 118.3(3) . . ?
C11 C2 B11 123.2(3) . . ?
C1 C2 B11 108.4(3) . . ?
C11 C2 B6 116.6(4) . . ?
C1 C2 B6 60.5(2) . . ?
B11 C2 B6 61.6(2) . . ?
C11 C2 B7 124.2(4) . . ?
C1 C2 B7 108.1(3) . . ?
B11 C2 B7 62.0(3) . . ?
B6 C2 B7 112.3(3) . . ?
C11 C2 B3 118.9(3) . . ?
C1 C2 B3 60.2(2) . . ?
B11 C2 B3 111.4(3) . . ?
B6 C2 B3 111.9(3) . . ?
B7 C2 B3 60.8(2) . . ?
N1 C12 C13 127.0(3) . . ?
N1 C12 C1 122.2(3) . . ?
C13 C12 C1 110.8(3) . . ?
C15 C13 C12 117.9(3) . . ?
C15 C13 C14 127.0(3) . . ?
C12 C13 C14 115.1(3) . . ?
C13 C14 B4 105.1(3) . . ?
C13 C15 C17 117.5(3) . . ?
C13 C15 C16 120.5(3) . . ?
C17 C15 C16 121.9(3) . . ?
C18 C17 C22 117.7(3) . . ?
C18 C17 C15 123.1(3) . . ?
C22 C17 C15 119.2(3) . . ?
C19 C18 C17 121.1(4) . . ?
C18 C19 C20 121.1(4) . . ?
C21 C20 C19 119.4(4) . . ?
C20 C21 C22 120.8(4) . . ?
N1 C22 C21 117.1(3) . . ?
N1 C22 C17 123.0(3) . . ?
C21 C22 C17 119.9(3) . . ?
C1 B3 C2 57.8(2) . . ?
C1 B3 B8 104.9(3) . . ?
C2 B3 B8 107.6(3) . . ?
C1 B3 B7 105.1(3) . . ?
C2 B3 B7 59.6(3) . . ?
B8 B3 B7 61.5(3) . . ?
C1 B3 B4 58.2(2) . . ?
C2 B3 B4 106.5(3) . . ?
B8 B3 B4 60.5(3) . . ?
B7 B3 B4 109.7(3) . . ?
C14 B4 C1 103.7(3) . . ?
C14 B4 B5 114.5(3) . . ?
C1 B4 B5 58.2(2) . . ?
C14 B4 B8 138.0(3) . . ?
C1 B4 B8 103.8(3) . . ?
B5 B4 B8 106.9(3) . . ?
C14 B4 B9 139.5(3) . . ?
C1 B4 B9 104.1(3) . . ?
B5 B4 B9 59.6(2) . . ?
B8 B4 B9 59.8(3) . . ?
C14 B4 B3 113.1(3) . . ?
C1 B4 B3 58.4(2) . . ?
B5 B4 B3 106.5(3) . . ?
B8 B4 B3 58.8(3) . . ?
B9 B4 B3 106.4(3) . . ?
C1 B5 B10 105.3(3) . . ?
C1 B5 B6 59.0(2) . . ?
B10 B5 B6 60.5(3) . . ?
C1 B5 B9 104.9(3) . . ?
B10 B5 B9 61.0(3) . . ?
B6 B5 B9 109.5(3) . . ?
C1 B5 B4 58.6(2) . . ?
B10 B5 B4 109.5(3) . . ?
B6 B5 B4 109.1(3) . . ?
B9 B5 B4 60.4(2) . . ?
C1 B6 C2 57.9(2) . . ?
C1 B6 B11 104.1(3) . . ?
C2 B6 B11 58.7(2) . . ?
C1 B6 B5 58.4(2) . . ?
C2 B6 B5 106.0(3) . . ?
B11 B6 B5 107.6(3) . . ?
C1 B6 B10 103.9(3) . . ?
C2 B6 B10 105.9(3) . . ?
B11 B6 B10 60.4(3) . . ?
B5 B6 B10 59.3(3) . . ?
C2 B7 B3 59.6(2) . . ?
C2 B7 B12 105.4(3) . . ?
B3 B7 B12 106.9(4) . . ?
C2 B7 B11 58.2(2) . . ?
B3 B7 B11 107.3(3) . . ?
B12 B7 B11 60.5(3) . . ?
C2 B7 B8 105.8(3) . . ?
B3 B7 B8 59.2(3) . . ?
B12 B7 B8 59.8(3) . . ?
B11 B7 B8 108.2(3) . . ?
B3 B8 B12 106.5(4) . . ?
B3 B8 B9 108.2(3) . . ?
B12 B8 B9 59.8(3) . . ?
B3 B8 B4 60.7(2) . . ?
B12 B8 B4 107.5(3) . . ?
B9 B8 B4 60.1(3) . . ?
B3 B8 B7 59.3(3) . . ?
B12 B8 B7 59.2(3) . . ?
B9 B8 B7 107.6(3) . . ?
B4 B8 B7 108.1(3) . . ?
B12 B9 B5 106.3(3) . . ?
B12 B9 B8 59.9(3) . . ?
B5 B9 B8 107.4(3) . . ?
B12 B9 B4 107.6(3) . . ?
B5 B9 B4 60.0(2) . . ?
B8 B9 B4 60.1(2) . . ?
B12 B9 B10 59.7(3) . . ?
B5 B9 B10 58.9(3) . . ?
B8 B9 B10 107.8(4) . . ?
B4 B9 B10 107.5(3) . . ?
B5 B10 B12 107.3(3) . . ?
B5 B10 B6 60.2(2) . . ?
B12 B10 B6 107.6(3) . . ?
B5 B10 B11 107.4(3) . . ?
B12 B10 B11 60.3(3) . . ?
B6 B10 B11 59.4(2) . . ?
B5 B10 B9 60.1(3) . . ?
B12 B10 B9 59.7(3) . . ?
B6 B10 B9 108.5(3) . . ?
B11 B10 B9 108.3(3) . . ?
C2 B11 B6 59.7(2) . . ?
C2 B11 B7 59.8(2) . . ?
B6 B11 B7 109.0(3) . . ?
C2 B11 B10 106.6(3) . . ?
B6 B11 B10 60.2(2) . . ?
B7 B11 B10 108.1(4) . . ?
C2 B11 B12 105.8(3) . . ?
B6 B11 B12 107.8(3) . . ?
B7 B11 B12 59.5(3) . . ?
B10 B11 B12 59.7(3) . . ?
B7 B12 B10 108.6(3) . . ?
B7 B12 B9 109.4(3) . . ?
B10 B12 B9 60.6(3) . . ?
B7 B12 B8 61.0(3) . . ?
B10 B12 B8 108.8(3) . . ?
B9 B12 B8 60.3(3) . . ?
B7 B12 B11 60.0(3) . . ?
B10 B12 B11 60.0(3) . . ?
B9 B12 B11 108.7(3) . . ?
B8 B12 B11 108.6(3) . . ?

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_lhr759b
_database_code_depnum_ccdc_archive 'CCDC 1823586'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 B10 Cl N O'
_chemical_formula_weight         365.89

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'
B B 0.0090 0.0039 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.4617(4)
_cell_length_b                   7.4840(3)
_cell_length_c                   23.7344(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.0865(14)
_cell_angle_gamma                90
_cell_volume                     2024.45(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    272
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.661
_shelx_estimated_absorpt_T_min   0.556
_shelx_estimated_absorpt_T_max   0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2328
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28912
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.746
_diffrn_reflns_theta_max         68.551
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3701
_reflns_number_gt                3052
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0780P)²+1.2633P] 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         3701
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Cl1 Cl -0.06967(7) 0.20803(11) -0.00076(4) 0.0865(3) Uani 1 1 d . . . . .
O1 O 0.35191(18) 0.2891(2) 0.25957(7) 0.0628(5) Uani 1 1 d . . . . .
N1 N 0.27702(14) 0.5680(2) 0.16217(7) 0.0378(4) Uani 1 1 d . . . . .
H1A H 0.2489 0.6616 0.1769 0.045 Uiso 1 1 calc R U . . .
C1 C 0.48972(16) 0.6382(3) 0.14661(8) 0.0332(4) Uani 1 1 d . . . . .
C2 C 0.46637(18) 0.7861(3) 0.09389(8) 0.0395(5) Uani 1 1 d . . . . .
C11 C 0.34548(19) 0.8140(4) 0.06284(10) 0.0508(6) Uani 1 1 d . . . . .
H11A H 0.3493 0.9036 0.0342 0.076 Uiso 1 1 calc R U . . .
H11B H 0.3179 0.7038 0.0455 0.076 Uiso 1 1 calc R U . . .
H11C H 0.2925 0.8522 0.0892 0.076 Uiso 1 1 calc R U . . .
C12 C 0.56168(18) 0.6272(4) 0.25423(9) 0.0472(6) Uani 1 1 d . . . . .
H12A H 0.6092 0.5237 0.2658 0.057 Uiso 1 1 calc R U . . .
H12B H 0.5712 0.7161 0.2841 0.057 Uiso 1 1 calc R U . . .
C13 C 0.43074(17) 0.5744(3) 0.24086(8) 0.0367(5) Uani 1 1 d . . . . .
H13A H 0.3848 0.6803 0.2487 0.044 Uiso 1 1 calc R U . . .
C14 C 0.39355(19) 0.4283(3) 0.27880(9) 0.0434(5) Uani 1 1 d . . . . .
C15 C 0.4109(3) 0.4641(4) 0.34113(10) 0.0709(8) Uani 1 1 d . . . . .
H15A H 0.4447 0.5806 0.3477 0.106 Uiso 1 1 calc R U . . .
H15B H 0.3366 0.4590 0.3563 0.106 Uiso 1 1 calc R U . . .
H15C H 0.4626 0.3757 0.3594 0.106 Uiso 1 1 calc R U . . .
C16 C 0.39909(15) 0.5300(3) 0.17713(8) 0.0326(4) Uani 1 1 d . . . . .
H16A H 0.4124 0.4023 0.1713 0.039 Uiso 1 1 calc R U . . .
C17 C 0.20041(16) 0.4660(3) 0.12585(8) 0.0357(4) Uani 1 1 d . . . . .
C18 C 0.23501(18) 0.3609(3) 0.08271(9) 0.0423(5) Uani 1 1 d . . . . .
H18A H 0.3145 0.3453 0.0794 0.051 Uiso 1 1 calc R U . . .
C19 C 0.1525(2) 0.2782(3) 0.04419(9) 0.0475(5) Uani 1 1 d . . . . .
H19A H 0.1767 0.2083 0.0152 0.057 Uiso 1 1 calc R U . . .
C20 C 0.0354(2) 0.3001(3) 0.04916(10) 0.0511(6) Uani 1 1 d . . . . .
C21 C -0.00114(19) 0.3966(3) 0.09316(12) 0.0557(6) Uani 1 1 d . . . . .
H21A H -0.0807 0.4071 0.0970 0.067 Uiso 1 1 calc R U . . .
C22 C 0.08061(18) 0.4781(3) 0.13172(10) 0.0471(5) Uani 1 1 d . . . . .
H22A H 0.0557 0.5417 0.1619 0.056 Uiso 1 1 calc R U . . .
B3 B 0.4951(2) 0.8611(3) 0.16242(10) 0.0412(5) Uani 1 1 d . . . . .
H3 H 0.4302 0.9312 0.1853 0.049 Uiso 1 1 calc R U . . .
B4 B 0.5973(2) 0.7062(4) 0.19663(10) 0.0434(6) Uani 1 1 d . . . . .
B5 B 0.6234(2) 0.5403(4) 0.14611(11) 0.0470(6) Uani 1 1 d . . . . .
H5 H 0.6432 0.4014 0.1589 0.056 Uiso 1 1 calc R U . . .
B6 B 0.5363(2) 0.5888(4) 0.08208(10) 0.0433(6) Uani 1 1 d . . . . .
H6 H 0.4981 0.4833 0.0536 0.052 Uiso 1 1 calc R U . . .
B7 B 0.5602(2) 0.9631(4) 0.10648(12) 0.0526(7) Uani 1 1 d . . . . .
H7 H 0.5388 1.1010 0.0931 0.063 Uiso 1 1 calc R U . . .
B8 B 0.6461(2) 0.9146(4) 0.17162(12) 0.0559(7) Uani 1 1 d . . . . .
H8 H 0.6810 1.0204 0.2009 0.067 Uiso 1 1 calc R U . . .
B9 B 0.7266(2) 0.7156(5) 0.16126(13) 0.0584(8) Uani 1 1 d . . . . .
H9 H 0.8142 0.6926 0.1838 0.070 Uiso 1 1 calc R U . . .
B10 B 0.6884(2) 0.6412(5) 0.08985(13) 0.0584(8) Uani 1 1 d . . . . .
H10 H 0.7510 0.5697 0.0660 0.070 Uiso 1 1 calc R U . . .
B11 B 0.5861(2) 0.7950(4) 0.05693(11) 0.0512(7) Uani 1 1 d . . . . .
H11 H 0.5815 0.8239 0.0113 0.061 Uiso 1 1 calc R U . . .
B12 B 0.7030(2) 0.8731(5) 0.10568(13) 0.0616(8) Uani 1 1 d . . . . .
H12 H 0.7757 0.9526 0.0921 0.074 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C20 1.739(2) . ?
O1 C14 1.215(3) . ?
N1 C17 1.392(2) . ?
N1 C16 1.435(2) . ?
C1 C16 1.555(3) . ?
C1 C2 1.671(3) . ?
C1 B4 1.696(3) . ?
C1 B5 1.699(3) . ?
C1 B3 1.709(3) . ?
C1 B6 1.715(3) . ?
C2 C11 1.513(3) . ?
C2 B11 1.706(3) . ?
C2 B7 1.712(3) . ?
C2 B6 1.718(3) . ?
C2 B3 1.719(3) . ?
C12 C13 1.552(3) . ?
C12 B4 1.582(3) . ?
C13 C14 1.507(3) . ?
C13 C16 1.554(3) . ?
C14 C15 1.496(3) . ?
C17 C18 1.382(3) . ?
C17 C22 1.398(3) . ?
C18 C19 1.389(3) . ?
C19 C20 1.370(3) . ?
C20 C21 1.371(4) . ?
C21 C22 1.380(3) . ?
B3 B7 1.764(4) . ?
B3 B8 1.767(4) . ?
B3 B4 1.781(4) . ?
B4 B5 1.773(4) . ?
B4 B8 1.780(4) . ?
B4 B9 1.780(4) . ?
B5 B6 1.765(3) . ?
B5 B10 1.766(4) . ?
B5 B9 1.778(4) . ?
B6 B11 1.771(4) . ?
B6 B10 1.776(4) . ?
B7 B11 1.769(4) . ?
B7 B12 1.772(4) . ?
B7 B8 1.780(4) . ?
B8 B9 1.782(5) . ?
B8 B12 1.785(4) . ?
B9 B12 1.768(4) . ?
B9 B10 1.794(5) . ?
B10 B11 1.765(4) . ?
B10 B12 1.780(5) . ?
B11 B12 1.774(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N1 C16 125.39(17) . . ?
C16 C1 C2 129.19(15) . . ?
C16 C1 B4 107.57(15) . . ?
C2 C1 B4 111.86(16) . . ?
C16 C1 B5 115.19(17) . . ?
C2 C1 B5 110.71(15) . . ?
B4 C1 B5 62.96(15) . . ?
C16 C1 B3 114.59(16) . . ?
C2 C1 B3 61.13(13) . . ?
B4 C1 B3 63.06(14) . . ?
B5 C1 B3 114.25(17) . . ?
C16 C1 B6 126.17(17) . . ?
C2 C1 B6 60.97(13) . . ?
B4 C1 B6 114.68(16) . . ?
B5 C1 B6 62.25(13) . . ?
B3 C1 B6 113.53(17) . . ?
C11 C2 C1 121.44(17) . . ?
C11 C2 B11 119.27(18) . . ?
C1 C2 B11 109.69(16) . . ?
C11 C2 B7 120.28(19) . . ?
C1 C2 B7 109.51(16) . . ?
B11 C2 B7 62.31(16) . . ?
C11 C2 B6 117.27(19) . . ?
C1 C2 B6 60.79(12) . . ?
B11 C2 B6 62.28(15) . . ?
B7 C2 B6 113.46(18) . . ?
C11 C2 B3 119.32(18) . . ?
C1 C2 B3 60.54(13) . . ?
B11 C2 B3 112.94(17) . . ?
B7 C2 B3 61.88(14) . . ?
B6 C2 B3 112.88(16) . . ?
C13 C12 B4 104.53(16) . . ?
C14 C13 C12 113.05(17) . . ?
C14 C13 C16 112.04(17) . . ?
C12 C13 C16 111.99(15) . . ?
O1 C14 C15 122.1(2) . . ?
O1 C14 C13 121.51(19) . . ?
C15 C14 C13 116.4(2) . . ?
N1 C16 C13 108.63(15) . . ?
N1 C16 C1 117.61(16) . . ?
C13 C16 C1 104.10(15) . . ?
C18 C17 N1 124.02(17) . . ?
C18 C17 C22 118.21(19) . . ?
N1 C17 C22 117.69(19) . . ?
C17 C18 C19 120.8(2) . . ?
C20 C19 C18 119.7(2) . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 Cl1 120.5(2) . . ?
C21 C20 Cl1 118.84(19) . . ?
C20 C21 C22 119.8(2) . . ?
C21 C22 C17 120.7(2) . . ?
C1 B3 C2 58.34(12) . . ?
C1 B3 B7 105.40(18) . . ?
C2 B3 B7 58.87(14) . . ?
C1 B3 B8 105.11(19) . . ?
C2 B3 B8 106.14(18) . . ?
B7 B3 B8 60.55(15) . . ?
C1 B3 B4 58.11(13) . . ?
C2 B3 B4 105.66(18) . . ?
B7 B3 B4 108.36(18) . . ?
B8 B3 B4 60.23(15) . . ?
C12 B4 C1 104.95(16) . . ?
C12 B4 B5 113.6(2) . . ?
C1 B4 B5 58.60(13) . . ?
C12 B4 B8 137.3(2) . . ?
C1 B4 B8 105.08(17) . . ?
B5 B4 B8 107.86(18) . . ?
C12 B4 B9 136.6(2) . . ?
C1 B4 B9 105.15(18) . . ?
B5 B4 B9 60.03(17) . . ?
B8 B4 B9 60.08(17) . . ?
C12 B4 B3 114.82(19) . . ?
C1 B4 B3 58.82(13) . . ?
B5 B4 B3 107.30(17) . . ?
B8 B4 B3 59.49(15) . . ?
B9 B4 B3 107.40(18) . . ?
C1 B5 B6 59.31(12) . . ?
C1 B5 B10 105.87(18) . . ?
B6 B5 B10 60.41(15) . . ?
C1 B5 B4 58.44(13) . . ?
B6 B5 B4 108.53(18) . . ?
B10 B5 B4 109.1(2) . . ?
C1 B5 B9 105.1(2) . . ?
B6 B5 B9 109.0(2) . . ?
B10 B5 B9 60.81(17) . . ?
B4 B5 B9 60.18(16) . . ?
C1 B6 C2 58.25(12) . . ?
C1 B6 B5 58.44(12) . . ?
C2 B6 B5 105.51(18) . . ?
C1 B6 B11 104.76(19) . . ?
C2 B6 B11 58.53(14) . . ?
B5 B6 B11 107.27(19) . . ?
C1 B6 B10 104.75(18) . . ?
C2 B6 B10 105.2(2) . . ?
B5 B6 B10 59.83(14) . . ?
B11 B6 B10 59.68(16) . . ?
C2 B7 B3 59.25(13) . . ?
C2 B7 B11 58.67(15) . . ?
B3 B7 B11 107.8(2) . . ?
C2 B7 B12 105.5(2) . . ?
B3 B7 B12 107.9(2) . . ?
B11 B7 B12 60.15(18) . . ?
C2 B7 B8 105.85(18) . . ?
B3 B7 B8 59.80(14) . . ?
B11 B7 B8 108.4(2) . . ?
B12 B7 B8 60.36(17) . . ?
B3 B8 B7 59.65(14) . . ?
B3 B8 B4 60.28(14) . . ?
B7 B8 B4 107.69(18) . . ?
B3 B8 B9 107.9(2) . . ?
B7 B8 B9 107.3(2) . . ?
B4 B8 B9 59.96(16) . . ?
B3 B8 B12 107.22(19) . . ?
B7 B8 B12 59.59(16) . . ?
B4 B8 B12 107.3(2) . . ?
B9 B8 B12 59.42(18) . . ?
B12 B9 B5 107.19(19) . . ?
B12 B9 B4 108.0(2) . . ?
B5 B9 B4 59.79(15) . . ?
B12 B9 B8 60.37(18) . . ?
B5 B9 B8 107.57(18) . . ?
B4 B9 B8 59.96(16) . . ?
B12 B9 B10 59.96(18) . . ?
B5 B9 B10 59.28(16) . . ?
B4 B9 B10 107.53(18) . . ?
B8 B9 B10 108.2(2) . . ?
B11 B10 B5 107.45(18) . . ?
B11 B10 B6 60.00(15) . . ?
B5 B10 B6 59.76(14) . . ?
B11 B10 B12 60.06(17) . . ?
B5 B10 B12 107.2(2) . . ?
B6 B10 B12 107.9(2) . . ?
B11 B10 B9 107.5(2) . . ?
B5 B10 B9 59.91(16) . . ?
B6 B10 B9 107.77(18) . . ?
B12 B10 B9 59.31(18) . . ?
C2 B11 B10 106.24(17) . . ?
C2 B11 B7 59.02(15) . . ?
B10 B11 B7 108.7(2) . . ?
C2 B11 B6 59.19(13) . . ?
B10 B11 B6 60.32(16) . . ?
B7 B11 B6 108.26(17) . . ?
C2 B11 B12 105.69(19) . . ?
B10 B11 B12 60.39(19) . . ?
B7 B11 B12 60.01(17) . . ?
B6 B11 B12 108.38(19) . . ?
B9 B12 B7 108.28(19) . . ?
B9 B12 B11 108.2(2) . . ?
B7 B12 B11 59.84(16) . . ?
B9 B12 B10 60.72(18) . . ?
B7 B12 B10 107.85(19) . . ?
B11 B12 B10 59.55(17) . . ?
B9 B12 B8 60.21(18) . . ?
B7 B12 B8 60.06(17) . . ?
B11 B12 B8 107.94(18) . . ?
B10 B12 B8 108.6(2) . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_LHR735
_database_code_depnum_ccdc_archive 'CCDC 1823585'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 B10 N'
_chemical_formula_weight         360.46

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           40
_space_group_name_H-M_alt        'A m a 2'
_space_group_name_Hall           'A 2 -2a'

_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'
'x+1/2, -y, z'
'-x+1/2, y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.2240(3)
_cell_length_b                   24.5840(11)
_cell_length_c                   11.2382(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1995.85(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    203
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             748
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25052
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.315
_diffrn_reflns_theta_max         25.234
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1961
_reflns_number_gt                1786
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.1017P)²+0.3867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.7(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1961
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_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 0.7500 0.04037(13) 0.6453(3) 0.0449(8) Uani 1 2 d S T P . .
C1 C 0.7500 0.13260(15) 0.5638(4) 0.0463(9) Uani 1 2 d S T P . .
C2 C 0.6322(7) 0.12933(15) 0.4361(3) 0.0740(11) Uani 0.5 1 d . . P . .
B6 B 0.6322(7) 0.12933(15) 0.4361(3) 0.0740(11) Uani 0.5 1 d . . P . .
C11 C 0.5401(14) 0.0807(3) 0.4089(8) 0.090(3) Uani 0.5 1 d . . P . .
H11A H 0.4784 0.0843 0.3337 0.135 Uiso 0.5 1 calc R U P . .
H11B H 0.6282 0.0515 0.4047 0.135 Uiso 0.5 1 calc R U P . .
H11C H 0.4506 0.0730 0.4698 0.135 Uiso 0.5 1 calc R U P . .
C12 C 0.7500 0.09326(14) 0.6639(4) 0.0403(9) Uani 1 2 d S T P . .
C13 C 0.7500 0.11907(14) 0.7737(4) 0.0434(9) Uani 1 2 d S T P . .
C14 C 0.7500 0.18127(16) 0.7671(5) 0.0605(11) Uani 1 2 d S T P . .
H14A H 0.8592 0.1962 0.8053 0.073 Uiso 0.5 1 calc R U P . .
H14B H 0.6408 0.1962 0.8053 0.073 Uiso 0.5 1 calc R U P . .
C15 C 0.7500 0.08783(16) 0.8759(4) 0.0435(9) Uani 1 2 d S T P . .
C16 C 0.7500 0.1174(2) 0.9941(5) 0.0715(14) Uani 1 2 d S T P . .
C17 C 0.7500 0.03010(16) 0.8627(4) 0.0424(9) Uani 1 2 d S T P . .
C18 C 0.7500 -0.00934(18) 0.9604(4) 0.0538(10) Uani 1 2 d S T P . .
C19 C 0.7500 0.0034(3) 1.0802(5) 0.131(4) Uani 1 2 d S T P . .
H19A H 0.7500 0.0398 1.1028 0.157 Uiso 1 2 calc R U P . .
C20 C 0.7500 -0.0357(3) 1.1666(6) 0.138(4) Uani 1 2 d S T P . .
H20A H 0.7500 -0.0250 1.2460 0.166 Uiso 1 2 calc R U P . .
C21 C 0.7500 -0.0896(3) 1.1408(6) 0.093(2) Uani 1 2 d S T P . .
H21A H 0.7500 -0.1155 1.2012 0.112 Uiso 1 2 calc R U P . .
C22 C 0.7500 -0.10469(19) 1.0258(5) 0.0687(13) Uani 1 2 d S T P . .
H22A H 0.7500 -0.1415 1.0064 0.082 Uiso 1 2 calc R U P . .
C23 C 0.7500 -0.06530(16) 0.9337(4) 0.0520(11) Uani 1 2 d S T P . .
C24 C 0.7500 -0.08378(16) 0.8134(5) 0.0574(11) Uani 1 2 d S T P . .
H24A H 0.7500 -0.1209 0.7974 0.069 Uiso 1 2 calc R U P . .
C25 C 0.7500 -0.04822(16) 0.7235(4) 0.0526(10) Uani 1 2 d S T P . .
H25A H 0.7500 -0.0609 0.6456 0.063 Uiso 1 2 calc R U P . .
C26 C 0.7500 0.00902(14) 0.7452(3) 0.0414(9) Uani 1 2 d S T P . .
B3 B 0.5514(5) 0.16936(15) 0.5523(4) 0.0601(9) Uani 1 1 d . . . . .
H3 H 0.4312 0.1697 0.6124 0.072 Uiso 1 1 calc R U . . .
B4 B 0.7500 0.19466(18) 0.6289(5) 0.0526(11) Uani 1 2 d S T P . .
B5 B 0.5528(7) 0.19451(18) 0.4068(4) 0.0770(13) Uani 1 1 d . . . . .
H5 H 0.4342 0.2137 0.3620 0.092 Uiso 1 1 calc R U . . .
B7 B 0.6260(6) 0.23681(15) 0.5267(4) 0.0678(10) Uani 1 1 d . . . . .
H7 H 0.5454 0.2722 0.5566 0.081 Uiso 1 1 calc R U . . .
B8 B 0.7500 0.1676(3) 0.3335(6) 0.0835(19) Uani 1 2 d S T P . .
H8 H 0.7500 0.1733 0.2365 0.100 Uiso 1 2 calc R U P . .
B9 B 0.7500 0.2367(3) 0.3911(7) 0.0770(18) Uani 1 2 d S T P . .
H9 H 0.7500 0.2726 0.3326 0.092 Uiso 1 2 calc R U P . .
H16A H 0.806(5) 0.1584(17) 0.974(4) 0.023(12) Uiso 0.5 1 d . . P . .
H16B H 0.852(6) 0.1132(17) 1.043(4) 0.104(15) 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 C12 1.317(5) . ?
N1 C26 1.361(5) . ?
C1 C12 1.483(5) . ?
C1 B6 1.671(5) 4_655 ?
C1 C2 1.671(5) 4_655 ?
C1 C2 1.671(5) . ?
C1 B4 1.692(6) . ?
C1 B3 1.700(4) . ?
C1 B3 1.700(4) 4_655 ?
C2 C11 1.402(9) . ?
C2 B6 1.703(9) 4_655 ?
C2 C2 1.703(9) 4_655 ?
C2 B8 1.713(7) . ?
C2 B5 1.733(6) . ?
C2 B3 1.736(6) . ?
C12 C13 1.388(5) . ?
C13 C15 1.382(6) . ?
C13 C14 1.531(5) . ?
C14 B4 1.587(7) . ?
C15 C17 1.427(5) . ?
C15 C16 1.514(6) . ?
C17 C26 1.418(5) . ?
C17 C18 1.465(6) . ?
C18 C19 1.383(8) . ?
C18 C23 1.408(6) . ?
C19 C20 1.367(8) . ?
C20 C21 1.355(10) . ?
C21 C22 1.345(9) . ?
C22 C23 1.417(6) . ?
C23 C24 1.426(7) . ?
C24 C25 1.335(7) . ?
C25 C26 1.428(5) . ?
B3 B5 1.748(6) . ?
B3 B7 1.767(5) . ?
B3 B4 1.785(5) . ?
B4 B3 1.785(5) 4_655 ?
B4 B7 1.787(6) . ?
B4 B7 1.787(6) 4_655 ?
B5 B9 1.772(6) . ?
B5 B8 1.774(7) . ?
B5 B7 1.782(7) . ?
B7 B9 1.768(8) . ?
B7 B7 1.791(8) 4_655 ?
B8 B6 1.714(7) 4_655 ?
B8 C2 1.714(7) 4_655 ?
B8 B5 1.774(7) 4_655 ?
B8 B9 1.819(10) . ?
B9 B7 1.768(8) 4_655 ?
B9 B5 1.772(6) 4_655 ?

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
C12 N1 C26 115.4(3) . . ?
C12 C1 B6 128.3(3) . 4_655 ?
C12 C1 C2 128.3(3) . 4_655 ?
B6 C1 C2 0.0 4_655 4_655 ?
C12 C1 C2 128.3(3) . . ?
B6 C1 C2 61.2 4_655 . ?
C2 C1 C2 61.2(4) 4_655 . ?
C12 C1 B4 105.1(3) . . ?
B6 C1 B4 114.5(3) 4_655 . ?
C2 C1 B4 114.5(3) 4_655 . ?
C2 C1 B4 114.5(3) . . ?
C12 C1 B3 113.8(2) . . ?
B6 C1 B3 113.0(3) 4_655 . ?
C2 C1 B3 113.0(3) 4_655 . ?
C2 C1 B3 62.0(2) . . ?
B4 C1 B3 63.49(19) . . ?
C12 C1 B3 113.8(2) . 4_655 ?
B6 C1 B3 62.0(2) 4_655 4_655 ?
C2 C1 B3 62.0(2) 4_655 4_655 ?
C2 C1 B3 113.0(3) . 4_655 ?
B4 C1 B3 63.49(19) . 4_655 ?
B3 C1 B3 115.1(3) . 4_655 ?
C11 C2 C1 118.0(4) . . ?
C11 C2 B6 118.3(5) . 4_655 ?
C1 C2 B6 59.38(18) . 4_655 ?
C11 C2 C2 118.3(5) . 4_655 ?
C1 C2 C2 59.38(18) . 4_655 ?
B6 C2 C2 0.0 4_655 4_655 ?
C11 C2 B8 123.9(5) . . ?
C1 C2 B8 107.4(3) . . ?
B6 C2 B8 60.21(18) 4_655 . ?
C2 C2 B8 60.21(18) 4_655 . ?
C11 C2 B5 126.2(5) . . ?
C1 C2 B5 106.7(3) . . ?
B6 C2 B5 109.3(2) 4_655 . ?
C2 C2 B5 109.3(2) 4_655 . ?
B8 C2 B5 61.9(3) . . ?
C11 C2 B3 119.2(6) . . ?
C1 C2 B3 59.83(19) . . ?
B6 C2 B3 109.63(18) 4_655 . ?
C2 C2 B3 109.63(18) 4_655 . ?
B8 C2 B3 111.2(4) . . ?
B5 C2 B3 60.5(2) . . ?
N1 C12 C13 126.3(3) . . ?
N1 C12 C1 121.6(3) . . ?
C13 C12 C1 112.1(3) . . ?
C15 C13 C12 119.0(3) . . ?
C15 C13 C14 126.5(4) . . ?
C12 C13 C14 114.4(4) . . ?
C13 C14 B4 104.8(4) . . ?
C13 C15 C17 117.8(4) . . ?
C13 C15 C16 117.6(4) . . ?
C17 C15 C16 124.7(4) . . ?
C26 C17 C15 117.4(3) . . ?
C26 C17 C18 117.1(4) . . ?
C15 C17 C18 125.4(4) . . ?
C19 C18 C23 115.4(5) . . ?
C19 C18 C17 125.5(5) . . ?
C23 C18 C17 119.1(4) . . ?
C20 C19 C18 122.2(6) . . ?
C21 C20 C19 122.4(7) . . ?
C22 C21 C20 118.4(5) . . ?
C21 C22 C23 120.9(5) . . ?
C18 C23 C22 120.8(4) . . ?
C18 C23 C24 120.9(4) . . ?
C22 C23 C24 118.3(4) . . ?
C25 C24 C23 120.5(4) . . ?
C24 C25 C26 121.1(4) . . ?
N1 C26 C17 124.1(3) . . ?
N1 C26 C25 114.7(3) . . ?
C17 C26 C25 121.2(4) . . ?
C1 B3 C2 58.2(2) . . ?
C1 B3 B5 104.7(3) . . ?
C2 B3 B5 59.7(2) . . ?
C1 B3 B7 104.7(3) . . ?
C2 B3 B7 107.9(3) . . ?
B5 B3 B7 60.9(2) . . ?
C1 B3 B4 58.0(2) . . ?
C2 B3 B4 106.9(3) . . ?
B5 B3 B4 108.9(3) . . ?
B7 B3 B4 60.4(2) . . ?
C14 B4 C1 103.6(3) . . ?
C14 B4 B3 113.5(2) . . ?
C1 B4 B3 58.49(18) . . ?
C14 B4 B3 113.5(2) . 4_655 ?
C1 B4 B3 58.49(18) . 4_655 ?
B3 B4 B3 107.0(4) . 4_655 ?
C14 B4 B7 138.5(3) . . ?
C1 B4 B7 104.2(3) . . ?
B3 B4 B7 59.3(2) . . ?
B3 B4 B7 107.2(3) 4_655 . ?
C14 B4 B7 138.5(3) . 4_655 ?
C1 B4 B7 104.2(3) . 4_655 ?
B3 B4 B7 107.2(3) . 4_655 ?
B3 B4 B7 59.3(2) 4_655 4_655 ?
B7 B4 B7 60.1(3) . 4_655 ?
C2 B5 B3 59.8(2) . . ?
C2 B5 B9 107.1(3) . . ?
B3 B5 B9 107.8(4) . . ?
C2 B5 B8 58.5(3) . . ?
B3 B5 B8 107.9(3) . . ?
B9 B5 B8 61.7(3) . . ?
C2 B5 B7 107.3(3) . . ?
B3 B5 B7 60.1(2) . . ?
B9 B5 B7 59.7(3) . . ?
B8 B5 B7 109.3(3) . . ?
B3 B7 B9 107.1(3) . . ?
B3 B7 B5 59.0(2) . . ?
B9 B7 B5 59.9(3) . . ?
B3 B7 B4 60.28(19) . . ?
B9 B7 B4 107.4(3) . . ?
B5 B7 B4 107.2(3) . . ?
B3 B7 B7 107.76(17) . 4_655 ?
B9 B7 B7 59.56(19) . 4_655 ?
B5 B7 B7 107.3(2) . 4_655 ?
B4 B7 B7 59.93(16) . 4_655 ?
C2 B8 B6 59.6 . 4_655 ?
C2 B8 C2 59.6(4) . 4_655 ?
B6 B8 C2 0.0 4_655 4_655 ?
C2 B8 B5 107.0(4) . 4_655 ?
B6 B8 B5 59.6(2) 4_655 4_655 ?
C2 B8 B5 59.6(2) 4_655 4_655 ?
C2 B8 B5 59.6(2) . . ?
B6 B8 B5 107.0(4) 4_655 . ?
C2 B8 B5 107.0(4) 4_655 . ?
B5 B8 B5 106.9(5) 4_655 . ?
C2 B8 B9 105.9(4) . . ?
B6 B8 B9 105.9(4) 4_655 . ?
C2 B8 B9 105.9(4) 4_655 . ?
B5 B8 B9 59.1(3) 4_655 . ?
B5 B8 B9 59.1(3) . . ?
B7 B9 B7 60.9(4) . 4_655 ?
B7 B9 B5 60.5(3) . . ?
B7 B9 B5 108.8(4) 4_655 . ?
B7 B9 B5 108.8(4) . 4_655 ?
B7 B9 B5 60.5(3) 4_655 4_655 ?
B5 B9 B5 107.1(4) . 4_655 ?
B7 B9 B8 107.9(3) . . ?
B7 B9 B8 107.9(3) 4_655 . ?
B5 B9 B8 59.2(3) . . ?
B5 B9 B8 59.2(3) 4_655 . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034

_shelxl_version_number           2014/6

