# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1564301'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2017-09-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H32 B Co N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         456.24

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.9166(17)
_cell_length_b                   13.444(2)
_cell_length_c                   16.223(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.171(2)
_cell_angle_gamma                90
_cell_volume                     2362.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5941
_cell_measurement_theta_min      2.4147
_cell_measurement_theta_max      26.2428
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964

_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
A X--ray quality crystal was selected under ambient conditions
and covered with PARATONE oil
The crystal was mounted and centered in the X--ray beam by
using a video camera.The crystal evaluation and data
collection with the detector to crystal distance of 5cm till resolution of 0.68
Å..
The initial cell constants were obtained from three series of
scans at different starting angles. Each series consisted
of 30 frames collected at intervals of 0.3 in a 10 range about
ω with the exposure time of 20 seconds per frame. The
obtained reflections were successfully indexed. The final cell
constants were calculated from a set of strong reflections based
upon the actual data collection.
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'X-ray tuve'
_diffrn_source_type              'Sealed tube'

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ' full spere ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            24315
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         28.41
_diffrn_reflns_theta_full        28.41
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
The systematic absences in the diffraction data were consistent for the
stated space group. The position of almost all non-hydrogen atoms
were found by direct methods. The remaining atoms were located in an
alternating series of least-squares cycles on difference Fourier maps.
All non-hydrogen atoms were refined in full-matrix anisotropic approximation.
All hydrogen atoms were placed in the structure factor calculation at
idealized positions and were allowed to ride on the neighboring atoms with
relative isotropic displacement coefficients.

Final results were tested with CHECKCIF routine and all A-warnings (if any)
were addressed on the very top of this file.
;

_reflns_number_total             5916
_reflns_number_gt                4634
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0880
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_number_reflns         5916
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.9556P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.350
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 Suite (Bruker AXS, 2013)'
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2013)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co Co1 0.18747(2) 0.22561(2) 0.53585(2) 0.02613(8) Uani d . . . 1 . .
B B1 0.45920(17) 0.22150(13) 0.61723(11) 0.0228(3) Uani d . . . 1 . .
C C1 0.1637(2) -0.01824(14) 0.61133(13) 0.0441(5) Uani d . . . 1 . .
H H1A 0.1038 0.011 0.5681 0.066 Uiso calc U . R 1 . .
H H1B 0.1276 -0.0772 0.6344 0.066 Uiso calc U . R 1 . .
H H1C 0.2383 -0.0373 0.5872 0.066 Uiso calc U . R 1 . .
C C2 0.19707(15) 0.05752(12) 0.68003(11) 0.0287(4) Uani d . . . 1 . .
C C3 0.08454(19) 0.08408(17) 0.72192(15) 0.0498(5) Uani d . . . 1 . .
H H3A 0.1068 0.1353 0.7641 0.075 Uiso calc U . R 1 . .
H H3B 0.055 0.0247 0.7484 0.075 Uiso calc U . R 1 . .
H H3C 0.0192 0.1093 0.6803 0.075 Uiso calc U . R 1 . .
C C4 0.30723(16) 0.02483(13) 0.74195(11) 0.0319(4) Uani d . . . 1 . .
H H4A 0.2943 0.0427 0.7994 0.038 Uiso calc U . R 1 . .
H H4B 0.32 -0.0479 0.739 0.038 Uiso calc U . R 1 . .
C C5 0.36576(15) 0.14941(11) 0.66199(9) 0.0225(3) Uani d . . . 1 . .
C C6 0.1439(2) 0.47633(17) 0.62067(16) 0.0547(6) Uani d . . . 1 . .
H H6A 0.0723 0.4441 0.5891 0.082 Uiso calc U . R 1 . .
H H6B 0.1292 0.5481 0.6232 0.082 Uiso calc U . R 1 . .
H H6C 0.1565 0.4491 0.6771 0.082 Uiso calc U . R 1 . .
C C7 0.25793(17) 0.45717(12) 0.57822(11) 0.0324(4) Uani d . . . 1 . .
C C8 0.2399(3) 0.49519(19) 0.48966(15) 0.0641(7) Uani d . . . 1 . .
H H8A 0.3143 0.4818 0.4634 0.096 Uiso calc U . R 1 . .
H H8B 0.2245 0.567 0.4897 0.096 Uiso calc U . R 1 . .
H H8C 0.1692 0.4614 0.4585 0.096 Uiso calc U . R 1 . .
C C9 0.37672(18) 0.49659(14) 0.62829(15) 0.0461(5) Uani d . . . 1 . .
H H9A 0.413 0.5506 0.5977 0.055 Uiso calc U . R 1 . .
H H9B 0.3596 0.5226 0.6828 0.055 Uiso calc U . R 1 . .
C C10 0.39474(15) 0.33145(11) 0.60994(10) 0.0242(3) Uani d . . . 1 . .
C C11 0.2602(2) 0.03200(16) 0.38691(13) 0.0513(6) Uani d . . . 1 . .
H H11A 0.2855 -0.0148 0.4321 0.077 Uiso calc U . R 1 . .
H H11B 0.269 0.0004 0.3335 0.077 Uiso calc U . R 1 . .
H H11C 0.1738 0.051 0.3883 0.077 Uiso calc U . R 1 . .
C C12 0.34126(18) 0.12408(13) 0.39745(10) 0.0342(4) Uani d . . . 1 . .
C C13 0.3034(2) 0.20039(17) 0.32973(13) 0.0519(6) Uani d . . . 1 . .
H H13A 0.2162 0.2175 0.3298 0.078 Uiso calc U . R 1 . .
H H13B 0.3157 0.1724 0.2756 0.078 Uiso calc U . R 1 . .
H H13C 0.354 0.2604 0.3402 0.078 Uiso calc U . R 1 . .
C C14 0.4793(2) 0.09881(16) 0.40506(12) 0.0432(5) Uani d . . . 1 . .
H H14A 0.4916 0.0259 0.4037 0.052 Uiso calc U . R 1 . .
H H14B 0.5177 0.1293 0.359 0.052 Uiso calc U . R 1 . .
C C15 0.43874(15) 0.17671(12) 0.52186(10) 0.0257(3) Uani d . . . 1 . .
C C16 0.59884(15) 0.22885(11) 0.66218(10) 0.0253(3) Uani d . . . 1 . .
C C17 0.69750(17) 0.25245(15) 0.61926(13) 0.0398(4) Uani d . . . 1 . .
H H17 0.6836 0.2582 0.5605 0.048 Uiso calc U . R 1 . .
C C18 0.81595(18) 0.26789(17) 0.65979(15) 0.0489(5) Uani d . . . 1 . .
H H18 0.8813 0.2838 0.6286 0.059 Uiso calc U . R 1 . .
C C19 0.83889(18) 0.26016(15) 0.74495(15) 0.0439(5) Uani d . . . 1 . .
H H19 0.9198 0.2707 0.7725 0.053 Uiso calc U . R 1 . .
C C20 0.74410(18) 0.23716(14) 0.78965(13) 0.0373(4) Uani d . . . 1 . .
H H20 0.7591 0.2315 0.8484 0.045 Uiso calc U . R 1 . .
C C21 0.62555(16) 0.22215(12) 0.74854(11) 0.0304(4) Uani d . . . 1 . .
H H21 0.5606 0.2068 0.7804 0.036 Uiso calc U . R 1 . .
C C22 0.0182(2) 0.24306(17) 0.47551(14) 0.0495(5) Uani d . . . 1 . .
H H22A -0.0254 0.2948 0.5029 0.074 Uiso calc U . R 1 . .
H H22B -0.0272 0.1802 0.476 0.074 Uiso calc U . R 1 . .
H H22C 0.024 0.2627 0.418 0.074 Uiso calc U . R 1 . .
N N1 0.24834(12) 0.14660(10) 0.64195(8) 0.0255(3) Uani d . . . 1 . .
N N2 0.28371(13) 0.34914(10) 0.57760(9) 0.0272(3) Uani d . . . 1 . .
N N3 0.33170(13) 0.17071(11) 0.47928(8) 0.0299(3) Uani d . . . 1 . .
O O1 0.41194(10) 0.07842(8) 0.71673(7) 0.0270(2) Uani d . . . 1 . .
O O2 0.45979(11) 0.41202(9) 0.63919(9) 0.0383(3) Uani d . . . 1 . .
O O3 0.53260(12) 0.13959(10) 0.48453(8) 0.0369(3) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Co1 C22 . 1.994(2) ?
Co1 N2 . 2.0354(14) ?
Co1 N3 . 2.0559(14) ?
Co1 N1 . 2.0608(14) ?
B1 C16 . 1.609(2) ?
B1 C10 . 1.635(2) ?
B1 C5 . 1.641(2) ?
B1 C15 . 1.649(2) ?
C1 C2 . 1.520(3) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 N1 . 1.488(2) ?
C2 C3 . 1.519(3) ?
C2 C4 . 1.532(2) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C3 H3C . 0.98 ?
C4 O1 . 1.452(2) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 N1 . 1.283(2) ?
C5 O1 . 1.3572(18) ?
C6 C7 . 1.518(3) ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 N2 . 1.480(2) ?
C7 C8 . 1.514(3) ?
C7 C9 . 1.536(3) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 O2 . 1.451(2) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 N2 . 1.282(2) ?
C10 O2 . 1.3486(19) ?
C11 C12 . 1.519(3) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 N3 . 1.484(2) ?
C12 C13 . 1.522(3) ?
C12 C14 . 1.534(3) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 O3 . 1.454(2) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 N3 . 1.284(2) ?
C15 O3 . 1.349(2) ?
C16 C17 . 1.390(3) ?
C16 C21 . 1.398(2) ?
C17 C18 . 1.391(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.377(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.371(3) ?
C19 H19 . 0.95 ?
C20 C21 . 1.395(3) ?
C20 H20 . 0.95 ?
C21 H21 . 0.95 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C22 Co1 N2 . . 118.39(8) ?
C22 Co1 N3 . . 122.52(8) ?
N2 Co1 N3 . . 92.82(6) ?
C22 Co1 N1 . . 130.77(8) ?
N2 Co1 N1 . . 92.49(5) ?
N3 Co1 N1 . . 90.16(6) ?
C16 B1 C10 . . 110.62(13) ?
C16 B1 C5 . . 116.23(13) ?
C10 B1 C5 . . 106.28(13) ?
C16 B1 C15 . . 117.22(14) ?
C10 B1 C15 . . 104.81(12) ?
C5 B1 C15 . . 100.40(12) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 C1 . . 107.63(14) ?
N1 C2 C3 . . 111.32(15) ?
C1 C2 C3 . . 110.64(16) ?
N1 C2 C4 . . 101.41(13) ?
C1 C2 C4 . . 112.65(15) ?
C3 C2 C4 . . 112.74(16) ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O1 C4 C2 . . 104.71(13) ?
O1 C4 H4A . . 110.8 ?
C2 C4 H4A . . 110.8 ?
O1 C4 H4B . . 110.8 ?
C2 C4 H4B . . 110.8 ?
H4A C4 H4B . . 108.9 ?
N1 C5 O1 . . 115.01(14) ?
N1 C5 B1 . . 124.19(14) ?
O1 C5 B1 . . 120.28(13) ?
C7 C6 H6A . . 109.5 ?
C7 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C7 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
N2 C7 C8 . . 109.09(16) ?
N2 C7 C6 . . 109.70(16) ?
C8 C7 C6 . . 110.87(18) ?
N2 C7 C9 . . 101.16(13) ?
C8 C7 C9 . . 112.73(18) ?
C6 C7 C9 . . 112.82(17) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O2 C9 C7 . . 105.52(14) ?
O2 C9 H9A . . 110.6 ?
C7 C9 H9A . . 110.6 ?
O2 C9 H9B . . 110.6 ?
C7 C9 H9B . . 110.6 ?
H9A C9 H9B . . 108.8 ?
N2 C10 O2 . . 115.13(14) ?
N2 C10 B1 . . 125.02(14) ?
O2 C10 B1 . . 119.85(13) ?
C12 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C12 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N3 C12 C11 . . 109.88(15) ?
N3 C12 C13 . . 108.54(15) ?
C11 C12 C13 . . 111.49(17) ?
N3 C12 C14 . . 101.52(14) ?
C11 C12 C14 . . 112.40(17) ?
C13 C12 C14 . . 112.49(17) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O3 C14 C12 . . 105.56(14) ?
O3 C14 H14A . . 110.6 ?
C12 C14 H14A . . 110.6 ?
O3 C14 H14B . . 110.6 ?
C12 C14 H14B . . 110.6 ?
H14A C14 H14B . . 108.8 ?
N3 C15 O3 . . 115.24(15) ?
N3 C15 B1 . . 122.37(14) ?
O3 C15 B1 . . 122.32(14) ?
C17 C16 C21 . . 116.04(16) ?
C17 C16 B1 . . 122.45(15) ?
C21 C16 B1 . . 121.18(15) ?
C16 C17 C18 . . 121.99(19) ?
C16 C17 H17 . . 119.0 ?
C18 C17 H17 . . 119.0 ?
C19 C18 C17 . . 120.3(2) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C20 C19 C18 . . 119.54(18) ?
C20 C19 H19 . . 120.2 ?
C18 C19 H19 . . 120.2 ?
C19 C20 C21 . . 119.76(19) ?
C19 C20 H20 . . 120.1 ?
C21 C20 H20 . . 120.1 ?
C20 C21 C16 . . 122.34(17) ?
C20 C21 H21 . . 118.8 ?
C16 C21 H21 . . 118.8 ?
Co1 C22 H22A . . 109.5 ?
Co1 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
Co1 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C5 N1 C2 . . 109.52(13) ?
C5 N1 Co1 . . 113.84(11) ?
C2 N1 Co1 . . 131.50(10) ?
C10 N2 C7 . . 110.50(13) ?
C10 N2 Co1 . . 114.04(11) ?
C7 N2 Co1 . . 135.44(11) ?
C15 N3 C12 . . 110.31(14) ?
C15 N3 Co1 . . 115.70(11) ?
C12 N3 Co1 . . 133.99(12) ?
C5 O1 C4 . . 106.98(12) ?
C10 O2 C9 . . 107.03(13) ?
C15 O3 C14 . . 107.17(14) ?


