# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_C1_a
_database_code_depnum_ccdc_archive 'CCDC 1487136'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2017-01-30 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            'C15 H12 B Cl O3'
_chemical_formula_weight         286.51

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   13.0121(10)
_cell_length_b                   5.2339(4)
_cell_length_c                   19.8200(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1349.82(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    142(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .09
_exptl_absorpt_coefficient_mu    0.285
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      142(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30213
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.583
_diffrn_reflns_theta_max         28.702
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3472
_reflns_number_gt                2888
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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)+(0.1000P)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_abs_structure_details 
;
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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
Cl01 Cl 0.57530(5) -0.0179(2) 0.12692(4) 0.0583(3) Uani 1 1 d . . . . .
O002 O 0.61124(14) 0.7010(3) 0.48409(9) 0.0293(4) Uani 1 1 d . . . . .
O003 O 0.45759(15) 0.9163(4) 0.51092(10) 0.0374(4) Uani 1 1 d . . . . .
H003 H 0.4131 0.9240 0.5415 0.056 Uiso 1 1 calc R U . . .
O004 O 0.80021(14) 0.5489(4) 0.39071(10) 0.0381(5) Uani 1 1 d . . . . .
C10 C 0.62469(18) 0.4020(4) 0.57235(11) 0.0236(5) Uani 1 1 d . . . . .
C4 C 0.63703(17) 0.0508(5) 0.32264(12) 0.0278(5) Uani 1 1 d . . . . .
H4 H 0.6194 -0.0354 0.3632 0.033 Uiso 1 1 calc R U . . .
C9 C 0.67661(17) 0.4971(4) 0.50921(11) 0.0247(5) Uani 1 1 d . . . . .
H9 H 0.7464 0.5655 0.5203 0.030 Uiso 1 1 calc R U . . .
C3 C 0.69835(17) 0.2716(4) 0.32541(13) 0.0255(5) Uani 1 1 d . . . . .
C12 C 0.47425(19) 0.4731(5) 0.64121(12) 0.0298(5) Uani 1 1 d . . . . .
H12 H 0.4128 0.5643 0.6508 0.036 Uiso 1 1 calc R U . . .
C11 C 0.53481(17) 0.5391(4) 0.58530(11) 0.0231(5) Uani 1 1 d . . . . .
C15 C 0.6560(2) 0.2013(5) 0.61374(12) 0.0290(5) Uani 1 1 d . . . . .
H15 H 0.7174 0.1096 0.6045 0.035 Uiso 1 1 calc R U . . .
C7 C 0.73344(19) 0.3826(4) 0.39039(13) 0.0272(5) Uani 1 1 d . . . . .
C14 C 0.5957(2) 0.1393(5) 0.66836(13) 0.0313(6) Uani 1 1 d . . . . .
H14 H 0.6161 0.0032 0.6971 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5054(2) 0.2721(5) 0.68237(12) 0.0320(6) Uani 1 1 d . . . . .
H13 H 0.4648 0.2251 0.7202 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6848(2) 0.2911(5) 0.45535(13) 0.0298(5) Uani 1 1 d . . . . .
H8A H 0.6151 0.2255 0.4453 0.036 Uiso 1 1 calc R U . . .
H8B H 0.7259 0.1474 0.4734 0.036 Uiso 1 1 calc R U . . .
C5 C 0.60200(18) -0.0425(5) 0.26149(13) 0.0317(5) Uani 1 1 d . . . . .
H5 H 0.5617 -0.1936 0.2597 0.038 Uiso 1 1 calc R U . . .
C2 C 0.7253(2) 0.3917(5) 0.26494(13) 0.0326(6) Uani 1 1 d . . . . .
H2 H 0.7698 0.5357 0.2660 0.039 Uiso 1 1 calc R U . . .
C1 C 0.6887(2) 0.3051(5) 0.20396(14) 0.0356(6) Uani 1 1 d . . . . .
H1 H 0.7054 0.3917 0.1633 0.043 Uiso 1 1 calc R U . . .
C6 C 0.62670(18) 0.0880(6) 0.20295(13) 0.0346(6) Uani 1 1 d . . . . .
B1 B 0.5275(2) 0.7356(5) 0.52649(14) 0.0278(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
Cl01 C6 1.739(3) . ?
O002 B1 1.388(3) . ?
O002 C9 1.453(3) . ?
O003 B1 1.348(3) . ?
O003 H003 0.8400 . ?
O004 C7 1.230(3) . ?
C10 C11 1.396(3) . ?
C10 C15 1.394(3) . ?
C10 C9 1.507(3) . ?
C4 C5 1.384(3) . ?
C4 C3 1.406(3) . ?
C4 H4 0.9500 . ?
C9 C8 1.521(3) . ?
C9 H9 1.0000 . ?
C3 C2 1.398(3) . ?
C3 C7 1.485(4) . ?
C12 C11 1.403(3) . ?
C12 C13 1.392(4) . ?
C12 H12 0.9500 . ?
C11 B1 1.557(3) . ?
C15 C14 1.375(4) . ?
C15 H15 0.9500 . ?
C7 C8 1.513(3) . ?
C14 C13 1.394(3) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C2 C1 1.376(4) . ?
C2 H2 0.9500 . ?
C1 C6 1.394(4) . ?
C1 H1 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
B1 O002 C9 110.36(18) . . ?
B1 O003 H003 109.5 . . ?
C11 C10 C15 121.6(2) . . ?
C11 C10 C9 111.00(19) . . ?
C15 C10 C9 127.4(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
O002 C9 C8 108.73(19) . . ?
O002 C9 C10 105.37(18) . . ?
C8 C9 C10 112.33(18) . . ?
O002 C9 H9 110.1 . . ?
C8 C9 H9 110.1 . . ?
C10 C9 H9 110.1 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 C7 119.4(2) . . ?
C4 C3 C7 122.0(2) . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 B1 104.7(2) . . ?
C12 C11 B1 136.0(2) . . ?
C14 C15 C10 118.4(2) . . ?
C14 C15 H15 120.8 . . ?
C10 C15 H15 120.8 . . ?
O004 C7 C3 119.9(2) . . ?
O004 C7 C8 121.0(2) . . ?
C3 C7 C8 119.1(2) . . ?
C15 C14 C13 121.3(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C8 C7 113.72(19) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C6 C1 C2 118.8(2) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C1 C6 C5 121.6(3) . . ?
C1 C6 Cl01 119.7(2) . . ?
C5 C6 Cl01 118.7(2) . . ?
O003 B1 O002 118.8(2) . . ?
O003 B1 C11 132.5(2) . . ?
O002 B1 C11 108.6(2) . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.047

