# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_02
_database_code_depnum_ccdc_archive 'CCDC 1465287'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H9 B O3'
_chemical_formula_moiety         'C18 H9 B O3'
_chemical_formula_weight         284.08
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   17.055(9)
_cell_length_b                   10.409(6)
_cell_length_c                   7.301(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.071(10)
_cell_angle_gamma                90.0000
_cell_volume                     1209.4(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3203
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.60
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584.00
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.995

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            4869
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1390
_reflns_number_gt                743
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1170
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1390
_refine_ls_number_parameters     102
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0587P)²+0.0000P] 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          0.000
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.26
_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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0 0.66584(14) 0.25 0.0239(5) Uani 1 4 d . . .
O13 O 0.14149(7) 0.26376(11) 0.49318(17) 0.0240(4) Uani 1 8 d . . .
C1 C 0.07363(10) 0.46767(15) 0.3781(2) 0.0197(4) Uani 1 8 d . . .
C2 C 0.0 0.2578(2) 0.25 0.0220(6) Uani 1 4 d . . .
C4 C 0.14109(11) 0.66855(17) 0.4950(3) 0.0255(5) Uani 1 8 d . . .
C5 C 0.07210(10) 0.60083(17) 0.3738(3) 0.0206(4) Uani 1 8 d . . .
C6 C 0.21007(11) 0.59690(17) 0.6140(3) 0.0264(5) Uani 1 8 d . . .
C7 C 0.21303(11) 0.46329(16) 0.6186(3) 0.0245(5) Uani 1 8 d . . .
C8 C 0.14305(11) 0.39827(17) 0.4974(2) 0.0211(4) Uani 1 8 d . . .
C9 C 0.07125(11) 0.19375(16) 0.3726(2) 0.0215(4) Uani 1 8 d . . .
C10 C 0.07199(11) 0.06131(17) 0.3741(3) 0.0262(5) Uani 1 8 d . . .
C11 C 0.0 -0.0009(2) 0.25 0.0300(7) Uani 1 4 d . . .
B12 B 0.0 0.3982(3) 0.25 0.0210(7) Uani 1 4 d . . .
H4 H 0.14162 0.75981 0.49733 0.0306 Uiso 1 8 calc R . .
H6 H 0.25793 0.64243 0.69702 0.0316 Uiso 1 8 calc R . .
H7 H 0.26128 0.41862 0.70172 0.0294 Uiso 1 8 calc R . .
H10 H 0.11944 0.01444 0.45596 0.0314 Uiso 1 8 calc R . .
H11 H 0.0 -0.09217 0.25 0.0360 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r15'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r15'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C5 1.4098(17) yes . .
O1 C5 1.4098(17) yes . 2_555
O13 C8 1.400(2) yes . .
O13 C9 1.4081(19) yes . .
C1 C5 1.386(2) yes . .
C1 C8 1.393(2) yes . .
C1 B12 1.459(2) yes . .
C2 C9 1.3929(19) yes . .
C2 C9 1.3929(19) yes . 2_555
C2 B12 1.461(4) yes . .
C4 C5 1.384(2) yes . .
C4 C6 1.400(2) yes . .
C6 C7 1.392(3) yes . .
C7 C8 1.381(2) yes . .
C9 C10 1.379(3) yes . .
C10 C11 1.3955(19) yes . .
C4 H4 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C5 O1 C5 122.63(15) yes . . 2_555
C8 O13 C9 122.43(12) yes . . .
C5 C1 C8 122.51(14) yes . . .
C5 C1 B12 118.42(16) yes . . .
C8 C1 B12 119.06(17) yes . . .
C9 C2 C9 122.81(18) yes . . 2_555
C9 C2 B12 118.60(10) yes . . .
C9 C2 B12 118.60(10) yes 2_555 . .
C5 C4 C6 117.20(16) yes . . .
O1 C5 C1 119.96(13) yes . . .
O1 C5 C4 120.69(16) yes . . .
C1 C5 C4 119.33(14) yes . . .
C4 C6 C7 124.22(15) yes . . .
C6 C7 C8 117.32(15) yes . . .
O13 C8 C1 119.96(14) yes . . .
O13 C8 C7 120.63(14) yes . . .
C1 C8 C7 119.41(16) yes . . .
O13 C9 C2 120.24(15) yes . . .
O13 C9 C10 120.62(14) yes . . .
C2 C9 C10 119.15(15) yes . . .
C9 C10 C11 117.10(15) yes . . .
C10 C11 C10 124.71(18) yes . . 2_555
C1 B12 C1 120.6(2) yes . . 2_555
C1 B12 C2 119.70(12) yes . . .
C1 B12 C2 119.70(12) yes 2_555 . .
C5 C4 H4 121.405 no . . .
C6 C4 H4 121.399 no . . .
C4 C6 H6 117.887 no . . .
C7 C6 H6 117.895 no . . .
C6 C7 H7 121.333 no . . .
C8 C7 H7 121.342 no . . .
C9 C10 H10 121.449 no . . .
C11 C10 H10 121.454 no . . .
C10 C11 H11 117.646 no . . .
C10 C11 H11 117.646 no 2_555 . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 O1 C5 C1 -0.6(2) no . . 2_555 2_555
C5 O1 C5 C4 -179.08(14) no . . 2_555 2_555
C5 O1 C5 C1 -0.6(2) no 2_555 . . .
C5 O1 C5 C4 -179.08(14) no 2_555 . . .
C8 O13 C9 C2 0.6(3) no . . . .
C8 O13 C9 C10 -179.43(16) no . . . .
C9 O13 C8 C1 -0.6(3) no . . . .
C9 O13 C8 C7 179.65(16) no . . . .
C5 C1 C8 O13 -178.94(17) no . . . .
C5 C1 C8 C7 0.8(3) no . . . .
C8 C1 C5 O1 -179.97(17) no . . . .
C8 C1 C5 C4 -1.4(3) no . . . .
C5 C1 B12 C1 -0.5(2) no . . . 2_555
C5 C1 B12 C2 179.47(13) no . . . .
B12 C1 C5 O1 1.0(3) no . . . .
B12 C1 C5 C4 179.60(13) no . . . .
C8 C1 B12 C1 -179.54(13) no . . . 2_555
C8 C1 B12 C2 0.5(2) no . . . .
B12 C1 C8 O13 0.0(3) no . . . .
B12 C1 C8 C7 179.82(13) no . . . .
C9 C2 C9 O13 179.91(14) no . . 2_555 2_555
C9 C2 C9 C10 -0.1(2) no . . 2_555 2_555
C9 C2 C9 O13 179.91(14) no 2_555 . . .
C9 C2 C9 C10 -0.1(2) no 2_555 . . .
C9 C2 B12 C1 -0.43(10) no . . . .
C9 C2 B12 C1 179.57(10) no . . . 2_555
B12 C2 C9 O13 -0.09(19) no . . . .
B12 C2 C9 C10 179.94(10) no . . . .
C9 C2 B12 C1 179.57(10) no 2_555 . . .
C9 C2 B12 C1 -0.43(10) no 2_555 . . 2_555
B12 C2 C9 O13 -0.09(19) no . . 2_555 2_555
B12 C2 C9 C10 179.94(10) no . . 2_555 2_555
C5 C4 C6 C7 -0.5(3) no . . . .
C6 C4 C5 O1 179.74(17) no . . . .
C6 C4 C5 C1 1.2(3) no . . . .
C4 C6 C7 C8 -0.1(3) no . . . .
C6 C7 C8 O13 179.68(17) no . . . .
C6 C7 C8 C1 -0.1(3) no . . . .
O13 C9 C10 C11 -179.86(16) no . . . .
C2 C9 C10 C11 0.1(3) no . . . .
C9 C10 C11 C10 -0.1(2) no . . . 2_555

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 C1 2.421(2) no . 2_555
O1 C4 2.4281(18) no . 2_555
O1 B12 2.786(4) no . .
O13 B12 2.802(2) no . .
C1 C5 2.862(2) no . 2_555
C1 C6 2.704(2) no . .
C1 C9 2.852(3) no . .
C2 C8 2.861(2) no . .
C2 C8 2.861(2) no . 2_555
C2 C10 2.390(3) no . 2_555
C2 C11 2.693(3) no . .
C4 C8 2.814(3) no . .
C5 C7 2.816(2) no . .
C9 C10 2.819(2) no . 2_555
O1 C11 3.469(3) no . 1_565
O13 C6 3.526(2) no . 6_546
C1 C6 3.579(3) no . 4_564
C5 C7 3.594(3) no . 4_564
C5 C8 3.377(3) no . 4_564
C5 B12 3.389(3) no . 3_566
C6 O13 3.526(2) no . 6_556
C6 C1 3.579(3) no . 4_565
C6 C8 3.383(3) no . 4_565
C7 C5 3.594(3) no . 4_565
C8 C5 3.377(3) no . 4_565
C8 C6 3.383(3) no . 4_564
C10 C11 3.444(3) no . 3_556
C11 O1 3.469(3) no . 1_545
C11 C10 3.444(3) no . 3_556
C11 C10 3.444(3) no . 4_554
B12 C5 3.389(3) no . 3_566
B12 C5 3.389(3) no . 4_564
O1 H4 2.6297 no . .
O1 H4 2.6297 no . 2_555
O13 H7 2.6180 no . .
O13 H10 2.6223 no . .
C1 H4 3.2594 no . .
C1 H7 3.2632 no . .
C2 H10 3.2596 no . .
C2 H10 3.2596 no . 2_555
C4 H7 3.3201 no . .
C5 H6 3.2286 no . .
C7 H4 3.3193 no . .
C8 H6 3.2200 no . .
C9 H11 3.2176 no . .
C10 H10 3.3236 no . 2_555
C11 H10 2.0576 no . 2_555
H4 H6 2.3396 no . .
H6 H7 2.3303 no . .
H10 H11 2.3323 no . .
O1 H11 2.5189 no . 1_565
O13 H6 3.5581 no . 4_564
O13 H6 2.6199 no . 6_546
O13 H7 3.1742 no . 7_556
C2 H4 3.5319 no . 3_566
C2 H4 3.5319 no . 4_564
C4 H6 3.2463 no . 7_566
C4 H7 3.5729 no . 4_564
C4 H7 3.4351 no . 6_556
C4 H11 3.4782 no . 1_565
C5 H11 3.4265 no . 1_565
C6 H4 3.2806 no . 7_566
C6 H7 3.4265 no . 4_564
C6 H7 3.5763 no . 6_556
C6 H10 3.5333 no . 6_556
C6 H10 3.3357 no . 7_556
C7 H6 3.5683 no . 6_546
C7 H10 3.4226 no . 6_556
C7 H10 3.1035 no . 7_556
C8 H6 3.4523 no . 4_564
C8 H6 3.4945 no . 6_546
C9 H4 3.3978 no . 4_564
C9 H6 3.4733 no . 6_546
C9 H7 3.3068 no . 7_556
C9 H11 3.5489 no . 3_556
C10 H4 3.3617 no . 1_545
C10 H6 3.5217 no . 6_546
C10 H7 3.0930 no . 7_556
C10 H10 3.5172 no . 4_554
C10 H11 3.4011 no . 3_556
C11 H4 3.4875 no . 1_545
C11 H4 3.4875 no . 2_545
C11 H10 3.4529 no . 3_556
C11 H10 3.4529 no . 4_554
H4 C2 3.5319 no . 3_566
H4 C6 3.2806 no . 7_566
H4 C9 3.3978 no . 4_565
H4 C10 3.3617 no . 1_565
H4 C11 3.4875 no . 1_565
H4 H6 2.7806 no . 7_566
H4 H7 2.7725 no . 6_556
H4 H10 2.6790 no . 1_565
H4 H11 2.8866 no . 1_565
H6 O13 3.5581 no . 4_565
H6 O13 2.6199 no . 6_556
H6 C4 3.2463 no . 7_566
H6 C7 3.5683 no . 6_556
H6 C8 3.4523 no . 4_565
H6 C8 3.4945 no . 6_556
H6 C9 3.4733 no . 6_556
H6 C10 3.5217 no . 6_556
H6 H4 2.7806 no . 7_566
H6 H6 3.5784 no . 7_566
H6 H7 3.0154 no . 6_556
H6 H10 2.9594 no . 6_556
H6 H10 3.1571 no . 7_556
H7 O13 3.1742 no . 7_556
H7 C4 3.5729 no . 4_565
H7 C4 3.4351 no . 6_546
H7 C6 3.4265 no . 4_565
H7 C6 3.5763 no . 6_546
H7 C9 3.3068 no . 7_556
H7 C10 3.0930 no . 7_556
H7 H4 2.7725 no . 6_546
H7 H6 3.0154 no . 6_546
H7 H10 2.7792 no . 6_556
H7 H10 2.7628 no . 7_556
H10 C6 3.5333 no . 6_546
H10 C6 3.3357 no . 7_556
H10 C7 3.4226 no . 6_546
H10 C7 3.1035 no . 7_556
H10 C10 3.5172 no . 4_555
H10 C11 3.4529 no . 3_556
H10 H4 2.6790 no . 1_545
H10 H6 2.9594 no . 6_546
H10 H6 3.1571 no . 7_556
H10 H7 2.7792 no . 6_546
H10 H7 2.7628 no . 7_556
H10 H11 3.5436 no . 3_556
H11 O1 2.5189 no . 1_545
H11 C4 3.4782 no . 1_545
H11 C4 3.4782 no . 2_545
H11 C5 3.4265 no . 1_545
H11 C5 3.4265 no . 2_545
H11 C9 3.5489 no . 3_556
H11 C9 3.5489 no . 4_554
H11 C10 3.4011 no . 3_556
H11 C10 3.4011 no . 4_554
H11 H4 2.8866 no . 1_545
H11 H4 2.8866 no . 2_545
H11 H10 3.5436 no . 3_556
H11 H10 3.5436 no . 4_554

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
