# 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_s16sel8
_database_code_depnum_ccdc_archive 'CCDC 1568176'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-10-10 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         'C16 H19 B O2'
_chemical_formula_sum            'C16 H19 B O2'
_chemical_formula_weight         254.12

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'
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                   10.4172(9)
_cell_length_b                   11.5094(9)
_cell_length_c                   12.3947(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.589(13)
_cell_angle_gamma                90
_cell_volume                     1465.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1306
_cell_measurement_theta_min      5.1150
_cell_measurement_theta_max      67.2600

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.573
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_T_min  0.91713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.687
_oxdiff_exptl_absorpt_empirical_full_max 1.231
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            8634
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.143
_diffrn_reflns_theta_max         68.416
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2686
_reflns_number_gt                1725
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_computing_structure_refinement  
;
 SHELXL-2014/8 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0858P)²+0.2194P] 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         2686
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1844
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
B B 0.5642(3) 0.5883(3) 0.2970(3) 0.0449(8) Uani 1 1 d . . . . .
O1 O 0.6461(2) 0.51771(16) 0.36502(18) 0.0570(6) Uani 1 1 d . . . . .
O2 O 0.54823(19) 0.55469(16) 0.19081(17) 0.0554(6) Uani 1 1 d . . . . .
C1 C 0.7119(3) 0.4446(2) 0.2951(3) 0.0536(8) Uani 1 1 d . . . . .
C2 C 0.7446(3) 0.3293(2) 0.3516(3) 0.0637(9) Uani 1 1 d . . . . .
H2A H 0.7885 0.2793 0.3051 0.095 Uiso 1 1 calc R U . . .
H2B H 0.6643 0.2916 0.3649 0.095 Uiso 1 1 calc R U . . .
H2C H 0.8022 0.3423 0.4216 0.095 Uiso 1 1 calc R U . . .
C3 C 0.8367(3) 0.5072(3) 0.2813(4) 0.0819(13) Uani 1 1 d . . . . .
H3A H 0.8847 0.4604 0.2353 0.123 Uiso 1 1 calc R U . . .
H3B H 0.8906 0.5189 0.3532 0.123 Uiso 1 1 calc R U . . .
H3C H 0.8152 0.5828 0.2464 0.123 Uiso 1 1 calc R U . . .
C4 C 0.6123(3) 0.4412(3) 0.1889(3) 0.0617(8) Uani 1 1 d . . . . .
C5 C 0.5075(4) 0.3496(3) 0.1912(4) 0.1046(17) Uani 1 1 d . . . . .
H5A H 0.5441 0.2724 0.1825 0.157 Uiso 1 1 calc R U . . .
H5B H 0.4351 0.3640 0.1313 0.157 Uiso 1 1 calc R U . . .
H5C H 0.4759 0.3536 0.2612 0.157 Uiso 1 1 calc R U . . .
C6 C 0.6722(5) 0.4340(4) 0.0858(3) 0.1000(15) Uani 1 1 d . . . . .
H6A H 0.7262 0.3641 0.0883 0.150 Uiso 1 1 calc R U . . .
H6B H 0.7262 0.5029 0.0806 0.150 Uiso 1 1 calc R U . . .
H6C H 0.6029 0.4305 0.0219 0.150 Uiso 1 1 calc R U . . .
C7 C 0.5019(2) 0.6977(2) 0.3394(2) 0.0435(6) Uani 1 1 d . . . . .
C8 C 0.5125(3) 0.7291(2) 0.4500(3) 0.0522(7) Uani 1 1 d . . . . .
H8 H 0.5561 0.6842 0.5092 0.063 Uiso 1 1 calc R U . . .
C9 C 0.4509(3) 0.8346(3) 0.4617(3) 0.0540(8) Uani 1 1 d . . . . .
H9 H 0.4446 0.8721 0.5289 0.065 Uiso 1 1 calc R U . . .
C10 C 0.3997(2) 0.8755(2) 0.3570(3) 0.0476(7) Uani 1 1 d . . . . .
C11 C 0.3364(3) 0.9811(2) 0.3336(3) 0.0553(8) Uani 1 1 d . . . . .
H11 H 0.3270 1.0274 0.3952 0.066 Uiso 1 1 calc R U . . .
C12 C 0.2855(3) 1.0279(3) 0.2333(3) 0.0616(9) Uani 1 1 d . . . . .
H12 H 0.2487 1.1032 0.2353 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2805(3) 0.9809(3) 0.1307(3) 0.0620(9) Uani 1 1 d . . . . .
H13 H 0.2381 1.0273 0.0720 0.074 Uiso 1 1 calc R U . . .
C14 C 0.3285(3) 0.8755(2) 0.1006(3) 0.0561(8) Uani 1 1 d . . . . .
H14 H 0.3124 0.8593 0.0244 0.067 Uiso 1 1 calc R U . . .
C15 C 0.3969(2) 0.7897(2) 0.1660(3) 0.0498(7) Uani 1 1 d . . . . .
H15 H 0.4230 0.7243 0.1281 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4316(2) 0.7872(2) 0.2786(2) 0.0420(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B O2 1.356(4) . ?
B O1 1.363(4) . ?
B C7 1.548(4) . ?
O1 C1 1.458(3) . ?
O2 C4 1.469(3) . ?
C1 C2 1.513(4) . ?
C1 C3 1.521(4) . ?
C1 C4 1.535(5) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C6 1.514(5) . ?
C4 C5 1.521(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.404(4) . ?
C7 C16 1.408(4) . ?
C8 C9 1.392(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 C16 1.482(4) . ?
C11 C12 1.377(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.396(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 B O1 113.1(2) . . ?
O2 B C7 124.8(3) . . ?
O1 B C7 122.0(3) . . ?
B O1 C1 106.5(2) . . ?
B O2 C4 106.7(2) . . ?
O1 C1 C2 108.8(2) . . ?
O1 C1 C3 106.8(2) . . ?
C2 C1 C3 109.7(3) . . ?
O1 C1 C4 101.9(2) . . ?
C2 C1 C4 116.3(3) . . ?
C3 C1 C4 112.6(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C6 108.3(3) . . ?
O2 C4 C5 106.6(3) . . ?
C6 C4 C5 112.1(3) . . ?
O2 C4 C1 102.0(2) . . ?
C6 C4 C1 114.2(3) . . ?
C5 C4 C1 112.7(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C16 106.5(2) . . ?
C8 C7 B 124.9(3) . . ?
C16 C7 B 128.6(3) . . ?
C9 C8 C7 111.4(3) . . ?
C9 C8 H8 124.3 . . ?
C7 C8 H8 124.3 . . ?
C8 C9 C10 107.9(3) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
C11 C10 C9 125.6(3) . . ?
C11 C10 C16 127.8(3) . . ?
C9 C10 C16 106.6(2) . . ?
C12 C11 C10 128.9(3) . . ?
C12 C11 H11 115.5 . . ?
C10 C11 H11 115.5 . . ?
C13 C12 C11 129.1(3) . . ?
C13 C12 H12 115.4 . . ?
C11 C12 H12 115.4 . . ?
C12 C13 C14 129.3(3) . . ?
C12 C13 H13 115.4 . . ?
C14 C13 H13 115.4 . . ?
C13 C14 C15 129.4(3) . . ?
C13 C14 H14 115.3 . . ?
C15 C14 H14 115.3 . . ?
C16 C15 C14 128.5(3) . . ?
C16 C15 H15 115.7 . . ?
C14 C15 H15 115.7 . . ?
C15 C16 C7 125.5(2) . . ?
C15 C16 C10 126.8(2) . . ?
C7 C16 C10 107.7(2) . . ?

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
O2 B O1 C1 12.8(3) . . . . ?
C7 B O1 C1 -165.0(2) . . . . ?
O1 B O2 C4 8.1(3) . . . . ?
C7 B O2 C4 -174.2(3) . . . . ?
B O1 C1 C2 -150.1(3) . . . . ?
B O1 C1 C3 91.5(3) . . . . ?
B O1 C1 C4 -26.8(3) . . . . ?
B O2 C4 C6 -144.8(3) . . . . ?
B O2 C4 C5 94.4(3) . . . . ?
B O2 C4 C1 -24.0(3) . . . . ?
O1 C1 C4 O2 30.4(3) . . . . ?
C2 C1 C4 O2 148.6(3) . . . . ?
C3 C1 C4 O2 -83.7(3) . . . . ?
O1 C1 C4 C6 147.0(3) . . . . ?
C2 C1 C4 C6 -94.8(4) . . . . ?
C3 C1 C4 C6 32.9(4) . . . . ?
O1 C1 C4 C5 -83.6(3) . . . . ?
C2 C1 C4 C5 34.6(4) . . . . ?
C3 C1 C4 C5 162.4(3) . . . . ?
O2 B C7 C8 176.3(3) . . . . ?
O1 B C7 C8 -6.2(4) . . . . ?
O2 B C7 C16 -7.6(4) . . . . ?
O1 B C7 C16 170.0(2) . . . . ?
C16 C7 C8 C9 0.4(3) . . . . ?
B C7 C8 C9 177.3(2) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C8 C9 C10 C11 -176.7(3) . . . . ?
C8 C9 C10 C16 0.9(3) . . . . ?
C9 C10 C11 C12 178.9(3) . . . . ?
C16 C10 C11 C12 1.8(5) . . . . ?
C10 C11 C12 C13 2.2(5) . . . . ?
C11 C12 C13 C14 -2.0(6) . . . . ?
C12 C13 C14 C15 -1.4(6) . . . . ?
C13 C14 C15 C16 1.7(5) . . . . ?
C14 C15 C16 C7 -179.5(3) . . . . ?
C14 C15 C16 C10 2.1(4) . . . . ?
C8 C7 C16 C15 -178.5(2) . . . . ?
B C7 C16 C15 4.7(4) . . . . ?
C8 C7 C16 C10 0.2(3) . . . . ?
B C7 C16 C10 -176.5(2) . . . . ?
C11 C10 C16 C15 -4.5(4) . . . . ?
C9 C10 C16 C15 178.0(2) . . . . ?
C11 C10 C16 C7 176.8(3) . . . . ?
C9 C10 C16 C7 -0.7(3) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043

