# Electronic Supplementary Material (ESI) for ChemComm.
# 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_Et2NCCBPh2_dimer
_database_code_depnum_ccdc_archive 'CCDC 1830300'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H40 B2 N2'
_chemical_formula_sum            'C36 H40 B2 N2'
_chemical_formula_weight         522.32

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

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

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

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

_cell_length_a                   9.3775(15)
_cell_length_b                   9.7968(14)
_cell_length_c                   10.2151(19)
_cell_angle_alpha                62.343(8)
_cell_angle_beta                 79.192(12)
_cell_angle_gamma                65.439(10)
_cell_volume                     756.0(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2544
_cell_measurement_theta_min      2.3881
_cell_measurement_theta_max      31.2666

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9096
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            6209
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3336
_reflns_number_gt                2307
_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       'RIGAKU CrystalClear'
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009(Wakita Nemoto et al.)'
_computing_publication_material  'Yadokari-XG 2009(Wakita,Nemoto et al.)'

_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)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3336
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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
C2 C 0.55721(15) 0.66913(15) 0.08802(13) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.52575(14) 0.58627(15) 0.04351(13) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.70450(14) 0.25748(15) 0.16481(13) 0.0151(3) Uani 1 1 d . . . . .
N1 N 0.59167(13) 0.75496(13) 0.13375(12) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.26835(15) 0.49243(17) 0.25548(14) 0.0226(3) Uani 1 1 d . . . . .
H8 H 0.2607 0.6040 0.1968 0.027 Uiso 1 1 calc R U . . .
C14 C 0.78106(15) 0.12821(16) 0.12216(14) 0.0196(3) Uani 1 1 d . . . . .
H14 H 0.7308 0.1224 0.0534 0.023 Uiso 1 1 calc R U . . .
C3 C 0.39590(14) 0.36372(16) 0.23574(13) 0.0163(3) Uani 1 1 d . . . . .
C13 C 0.92848(16) 0.00739(17) 0.17679(14) 0.0235(3) Uani 1 1 d . . . . .
H13 H 0.9764 -0.0798 0.1464 0.028 Uiso 1 1 calc R U . . .
C6 C 0.16084(16) 0.29979(18) 0.44545(15) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.0815 0.2785 0.5157 0.031 Uiso 1 1 calc R U . . .
C10 C 0.78564(15) 0.26077(16) 0.26523(13) 0.0200(3) Uani 1 1 d . . . . .
H10 H 0.7380 0.3467 0.2971 0.024 Uiso 1 1 calc R U . . .
C11 C 0.93291(16) 0.14246(17) 0.31896(14) 0.0238(3) Uani 1 1 d . . . . .
H11 H 0.9850 0.1488 0.3860 0.029 Uiso 1 1 calc R U . . .
C4 C 0.40071(16) 0.20189(16) 0.32526(14) 0.0211(3) Uani 1 1 d . . . . .
H4 H 0.4854 0.1111 0.3148 0.025 Uiso 1 1 calc R U . . .
C12 C 1.00486(15) 0.01453(17) 0.27534(14) 0.0247(3) Uani 1 1 d . . . . .
H12 H 1.1056 -0.0673 0.3129 0.030 Uiso 1 1 calc R U . . .
B1 B 0.52988(17) 0.39296(18) 0.11339(15) 0.0154(3) Uani 1 1 d . . . . .
C5 C 0.28550(17) 0.17001(18) 0.42894(15) 0.0253(3) Uani 1 1 d . . . . .
H5 H 0.2926 0.0587 0.4885 0.030 Uiso 1 1 calc R U . . .
C16 C 0.47000(19) 0.7403(2) 0.37563(15) 0.0350(4) Uani 1 1 d . . . . .
H16 H 0.4420 0.6478 0.3918 0.052 Uiso 1 1 calc R U . . .
H16A H 0.3922 0.8074 0.4228 0.052 Uiso 1 1 calc R U . . .
H16B H 0.5737 0.6963 0.4186 0.052 Uiso 1 1 calc R U . . .
C15 C 0.47315(18) 0.84754(18) 0.21165(15) 0.0294(3) Uani 1 1 d . . . . .
H15 H 0.3683 0.8911 0.1687 0.035 Uiso 1 1 calc R U . . .
H15A H 0.4963 0.9438 0.1960 0.035 Uiso 1 1 calc R U . . .
C18 C 0.86280(18) 0.6626(2) 0.03920(17) 0.0352(4) Uani 1 1 d . . . . .
H18 H 0.8735 0.5460 0.0843 0.053 Uiso 1 1 calc R U . . .
H18A H 0.9657 0.6676 0.0358 0.053 Uiso 1 1 calc R U . . .
H18B H 0.8210 0.7184 -0.0614 0.053 Uiso 1 1 calc R U . . .
C7 C 0.15220(16) 0.46141(18) 0.35883(15) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.0668 0.5514 0.3699 0.034 Uiso 1 1 calc R U . . .
C17 C 0.75355(17) 0.7474(2) 0.12892(18) 0.0345(4) Uani 1 1 d . . . . .
H17 H 0.7951 0.6878 0.2311 0.041 Uiso 1 1 calc R U . . .
H17A H 0.7506 0.8622 0.0874 0.041 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
C2 C1 1.2430(16) . ?
C2 N1 1.2949(16) . ?
C1 B1 1.6709(18) . ?
C1 B1 1.6747(18) 2_665 ?
C9 C14 1.3958(17) . ?
C9 C10 1.4058(17) . ?
C9 B1 1.6086(19) . ?
N1 C15 1.4803(17) . ?
N1 C17 1.4812(18) . ?
C8 C7 1.3925(18) . ?
C8 C3 1.3975(18) . ?
C8 H8 0.9500 . ?
C14 C13 1.3927(18) . ?
C14 H14 0.9500 . ?
C3 C4 1.4007(18) . ?
C3 B1 1.6126(19) . ?
C13 C12 1.3816(19) . ?
C13 H13 0.9500 . ?
C6 C5 1.379(2) . ?
C6 C7 1.3843(19) . ?
C6 H6 0.9500 . ?
C10 C11 1.3838(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3882(19) . ?
C11 H11 0.9500 . ?
C4 C5 1.3895(18) . ?
C4 H4 0.9500 . ?
C12 H12 0.9500 . ?
B1 C1 1.6748(18) 2_665 ?
C5 H5 0.9500 . ?
C16 C15 1.511(2) . ?
C16 H16 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C15 H15 0.9900 . ?
C15 H15A 0.9900 . ?
C18 C17 1.492(2) . ?
C18 H18 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C7 H7 0.9500 . ?
C17 H17 0.9900 . ?
C17 H17A 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
C1 C2 N1 179.31(14) . . ?
C2 C1 B1 136.58(12) . . ?
C2 C1 B1 138.65(12) . 2_665 ?
B1 C1 B1 84.69(9) . 2_665 ?
C14 C9 C10 116.19(12) . . ?
C14 C9 B1 124.33(11) . . ?
C10 C9 B1 119.40(11) . . ?
C2 N1 C15 120.28(11) . . ?
C2 N1 C17 122.14(11) . . ?
C15 N1 C17 117.09(11) . . ?
C7 C8 C3 121.76(13) . . ?
C7 C8 H8 119.1 . . ?
C3 C8 H8 119.1 . . ?
C13 C14 C9 122.38(12) . . ?
C13 C14 H14 118.8 . . ?
C9 C14 H14 118.8 . . ?
C8 C3 C4 116.50(11) . . ?
C8 C3 B1 123.82(12) . . ?
C4 C3 B1 119.63(11) . . ?
C12 C13 C14 119.86(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C5 C6 C7 119.49(12) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C11 C10 C9 121.92(13) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 120.32(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C5 C4 C3 122.05(13) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C13 C12 C11 119.32(13) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C9 B1 C3 115.15(10) . . ?
C9 B1 C1 110.99(10) . . ?
C3 B1 C1 112.19(10) . . ?
C9 B1 C1 112.86(10) . 2_665 ?
C3 B1 C1 108.65(10) . 2_665 ?
C1 B1 C1 95.31(9) . 2_665 ?
C6 C5 C4 120.06(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C15 C16 H16 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C15 C16 112.36(12) . . ?
N1 C15 H15 109.1 . . ?
C16 C15 H15 109.1 . . ?
N1 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
H15 C15 H15A 107.9 . . ?
C17 C18 H18 109.5 . . ?
C17 C18 H18A 109.5 . . ?
H18 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C7 C8 120.15(13) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N1 C17 C18 113.64(11) . . ?
N1 C17 H17 108.8 . . ?
C18 C17 H17 108.8 . . ?
N1 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
H17 C17 H17A 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C9 C14 C13 0.85(18) . . . . ?
B1 C9 C14 C13 -175.82(11) . . . . ?
C7 C8 C3 C4 0.05(19) . . . . ?
C7 C8 C3 B1 177.45(12) . . . . ?
C9 C14 C13 C12 -0.91(19) . . . . ?
C14 C9 C10 C11 -0.11(18) . . . . ?
B1 C9 C10 C11 176.74(11) . . . . ?
C9 C10 C11 C12 -0.59(19) . . . . ?
C8 C3 C4 C5 -0.27(18) . . . . ?
B1 C3 C4 C5 -177.78(12) . . . . ?
C14 C13 C12 C11 0.18(19) . . . . ?
C10 C11 C12 C13 0.55(19) . . . . ?
C14 C9 B1 C3 102.86(13) . . . . ?
C10 C9 B1 C3 -73.72(14) . . . . ?
C14 C9 B1 C1 -128.31(12) . . . . ?
C10 C9 B1 C1 55.12(14) . . . . ?
C14 C9 B1 C1 -22.69(16) . . . 2_665 ?
C10 C9 B1 C1 160.74(11) . . . 2_665 ?
C8 C3 B1 C9 142.94(12) . . . . ?
C4 C3 B1 C9 -39.74(16) . . . . ?
C8 C3 B1 C1 14.70(17) . . . . ?
C4 C3 B1 C1 -167.98(11) . . . . ?
C8 C3 B1 C1 -89.37(14) . . . 2_665 ?
C4 C3 B1 C1 87.94(13) . . . 2_665 ?
C2 C1 B1 C9 -60.03(19) . . . . ?
B1 C1 B1 C9 116.97(12) 2_665 . . . ?
C2 C1 B1 C3 70.37(19) . . . . ?
B1 C1 B1 C3 -112.63(12) 2_665 . . . ?
C2 C1 B1 C1 -176.99(18) . . . 2_665 ?
B1 C1 B1 C1 0.0 2_665 . . 2_665 ?
C7 C6 C5 C4 -0.5(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C2 N1 C15 C16 85.89(15) . . . . ?
C17 N1 C15 C16 -86.28(16) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C3 C8 C7 C6 0.0(2) . . . . ?
C2 N1 C17 C18 12.2(2) . . . . ?
C15 N1 C17 C18 -175.80(12) . . . . ?

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.072

_shelxl_version_number           2014-3

_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
