# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20180413b
_database_code_depnum_ccdc_archive 'CCDC 1841705'
_audit_update_record             
;
2018-05-06 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H27 B O3'
_chemical_formula_weight         278.18

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.2578(5)
_cell_length_b                   13.1115(6)
_cell_length_c                   10.1534(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.245(5)
_cell_angle_gamma                90
_cell_volume                     828.13(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1014
_cell_measurement_theta_min      0.92996
_cell_measurement_theta_max      1.00000

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.582
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2959
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.381
_diffrn_reflns_theta_max         72.247
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.720
_diffrn_reflns_point_group_measured_fraction_full 0.749
_reflns_number_total             2354
_reflns_number_gt                1816
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.423
_reflns_Friedel_fraction_max     0.449
_reflns_Friedel_fraction_full    0.478

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0890P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2354
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.004

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
C12 C 0.1711(7) 0.2344(3) 0.9833(3) 0.0552(8) Uani 1 1 d . . . . .
H12 H 0.2252 0.2636 0.9045 0.066 Uiso 1 1 calc R U . . .
O2 O 0.0002(5) 0.2917(2) 0.6649(2) 0.0651(7) Uani 1 1 d . . . . .
O1 O -0.1754(5) 0.4306(2) 0.7295(3) 0.0709(8) Uani 1 1 d . . . . .
C10 C -0.0365(7) 0.0990(3) 0.8440(3) 0.0626(10) Uani 1 1 d . . . . .
C13 C -0.0455(6) 0.2856(3) 0.9970(3) 0.0578(9) Uani 1 1 d . . . . .
H13A H -0.0230 0.3580 1.0127 0.069 Uiso 1 1 calc R U . . .
H13B H -0.1061 0.2572 1.0730 0.069 Uiso 1 1 calc R U . . .
C8 C -0.2455(6) 0.1562(3) 0.8451(3) 0.0627(10) Uani 1 1 d . . . . .
H8 H -0.3128 0.1299 0.9210 0.075 Uiso 1 1 calc R U . . .
C7 C -0.2059(6) 0.2706(3) 0.8720(3) 0.0550(8) Uani 1 1 d . . . . .
H7 H -0.3430 0.3009 0.8899 0.066 Uiso 1 1 calc R U . . .
C11 C 0.1355(7) 0.1202(3) 0.9560(4) 0.0635(10) Uani 1 1 d . . . . .
H11A H 0.2694 0.0901 0.9353 0.076 Uiso 1 1 calc R U . . .
H11B H 0.0964 0.0876 1.0357 0.076 Uiso 1 1 calc R U . . .
O3 O -0.0091(6) 0.0351(3) 0.7607(3) 0.0852(10) Uani 1 1 d . . . . .
C14 C 0.3382(7) 0.2572(3) 1.1001(3) 0.0658(10) Uani 1 1 d . . . . .
B1 B -0.1249(7) 0.3311(3) 0.7519(4) 0.0539(9) Uani 1 1 d . . . . .
C9 C -0.4053(8) 0.1365(4) 0.7235(4) 0.0796(12) Uani 1 1 d . . . . .
H9A H -0.5341 0.1750 0.7304 0.119 Uiso 1 1 calc R U . . .
H9B H -0.4394 0.0652 0.7181 0.119 Uiso 1 1 calc R U . . .
H9C H -0.3430 0.1570 0.6453 0.119 Uiso 1 1 calc R U . . .
C4 C 0.0125(7) 0.3674(3) 0.5591(3) 0.0610(9) Uani 1 1 d . . . . .
C5 C -0.1509(9) 0.3358(4) 0.4451(4) 0.0843(14) Uani 1 1 d . . . . .
H5A H -0.1189 0.2681 0.4172 0.126 Uiso 1 1 calc R U . . .
H5B H -0.1449 0.3823 0.3726 0.126 Uiso 1 1 calc R U . . .
H5C H -0.2923 0.3371 0.4735 0.126 Uiso 1 1 calc R U . . .
C3 C -0.0470(8) 0.4676(3) 0.6287(4) 0.0684(11) Uani 1 1 d . . . . .
C16 C 0.4009(9) 0.3665(4) 1.1185(5) 0.0864(13) Uani 1 1 d . . . . .
H16A H 0.5312 0.3712 1.1775 0.130 Uiso 1 1 calc R U . . .
H16B H 0.2884 0.4030 1.1554 0.130 Uiso 1 1 calc R U . . .
H16C H 0.4234 0.3957 1.0344 0.130 Uiso 1 1 calc R U . . .
C6 C 0.2349(9) 0.3634(4) 0.5155(5) 0.0843(13) Uani 1 1 d . . . . .
H6A H 0.2530 0.3004 0.4699 0.126 Uiso 1 1 calc R U . . .
H6B H 0.3397 0.3677 0.5917 0.126 Uiso 1 1 calc R U . . .
H6C H 0.2536 0.4195 0.4572 0.126 Uiso 1 1 calc R U . . .
C15 C 0.4240(11) 0.1859(5) 1.1815(5) 0.0907(16) Uani 1 1 d . . . . .
C1 C 0.1473(12) 0.5205(5) 0.7014(6) 0.119(2) Uani 1 1 d . . . . .
H1A H 0.1001 0.5740 0.7560 0.178 Uiso 1 1 calc R U . . .
H1B H 0.2339 0.5491 0.6382 0.178 Uiso 1 1 calc R U . . .
H1C H 0.2307 0.4720 0.7559 0.178 Uiso 1 1 calc R U . . .
C2 C -0.1824(12) 0.5414(4) 0.5398(5) 0.1057(19) Uani 1 1 d . . . . .
H2A H -0.3082 0.5069 0.4994 0.159 Uiso 1 1 calc R U . . .
H2B H -0.0999 0.5662 0.4721 0.159 Uiso 1 1 calc R U . . .
H2C H -0.2248 0.5976 0.5916 0.159 Uiso 1 1 calc R U . . .
H15A H 0.370(10) 0.113(5) 1.180(6) 0.11(2) Uiso 1 1 d . . . . .
H15B H 0.535(13) 0.196(6) 1.251(7) 0.14(3) 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
C12 C14 1.523(5) . ?
C12 C11 1.534(5) . ?
C12 C13 1.533(5) . ?
O2 B1 1.345(5) . ?
O2 C4 1.471(4) . ?
O1 B1 1.355(5) . ?
O1 C3 1.452(5) . ?
C10 O3 1.216(5) . ?
C10 C11 1.505(6) . ?
C10 C8 1.509(6) . ?
C13 C7 1.543(5) . ?
C8 C9 1.524(6) . ?
C8 C7 1.540(5) . ?
C7 B1 1.584(5) . ?
C14 C15 1.323(7) . ?
C14 C16 1.493(7) . ?
C4 C6 1.507(6) . ?
C4 C5 1.516(6) . ?
C4 C3 1.556(6) . ?
C3 C2 1.517(7) . ?
C3 C1 1.520(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C12 C11 113.9(3) . . ?
C14 C12 C13 112.5(3) . . ?
C11 C12 C13 109.4(3) . . ?
B1 O2 C4 107.5(3) . . ?
B1 O1 C3 107.6(3) . . ?
O3 C10 C11 120.7(4) . . ?
O3 C10 C8 122.4(4) . . ?
C11 C10 C8 116.8(3) . . ?
C12 C13 C7 111.8(3) . . ?
C10 C8 C9 113.7(3) . . ?
C10 C8 C7 111.3(3) . . ?
C9 C8 C7 112.8(3) . . ?
C13 C7 C8 110.3(3) . . ?
C13 C7 B1 109.6(3) . . ?
C8 C7 B1 114.2(3) . . ?
C10 C11 C12 113.3(3) . . ?
C15 C14 C16 121.1(4) . . ?
C15 C14 C12 123.1(4) . . ?
C16 C14 C12 115.8(4) . . ?
O2 B1 O1 113.7(3) . . ?
O2 B1 C7 124.8(3) . . ?
O1 B1 C7 121.5(3) . . ?
O2 C4 C6 108.3(3) . . ?
O2 C4 C5 106.8(3) . . ?
C6 C4 C5 109.5(4) . . ?
O2 C4 C3 101.8(3) . . ?
C6 C4 C3 115.9(4) . . ?
C5 C4 C3 113.7(4) . . ?
O1 C3 C2 108.5(4) . . ?
O1 C3 C1 106.6(4) . . ?
C2 C3 C1 111.3(5) . . ?
O1 C3 C4 102.5(3) . . ?
C2 C3 C4 114.4(4) . . ?
C1 C3 C4 112.8(5) . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033

