# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_4bmbf_070616_0m
_database_code_depnum_ccdc_archive 'CCDC 1510673'
_audit_update_record             
;
2016-10-19 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
#==================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        4BMBF
#==========================================================================
# CHEMICAL DATA

_chemical_name_common            'Boron diketonate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 B F2 O3 S'
_chemical_formula_sum            'C11 H11 B F2 O3 S'
_chemical_formula_weight         272.07

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'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#==========================================================================

# CRYSTAL DATA
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9630(18)
_cell_length_b                   8.0155(18)
_cell_length_c                   10.948(2)
_cell_angle_alpha                103.904(4)
_cell_angle_beta                 101.576(4)
_cell_angle_gamma                113.133(5)
_cell_volume                     588.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    925
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      25.44

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9008
_exptl_absorpt_correction_T_max  0.9431
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
#==========================================================================

# Experimental data 
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7056
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2063
_reflns_number_gt                1850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
#==========================================================================

# Refinement data 
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.2210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2063
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.03755(6) 0.88114(6) 0.69614(4) 0.01910(14) Uani 1 1 d . . .
F1 F 0.45503(13) 0.51938(13) 0.73975(9) 0.0200(2) Uani 1 1 d . . .
O3 O -0.03273(17) 0.69187(17) 0.07764(12) 0.0220(3) Uani 1 1 d . . .
C6 C 0.4117(2) 0.7938(2) 0.31578(17) 0.0179(4) Uani 1 1 d . . .
H6 H 0.5448 0.8446 0.3240 0.021 Uiso 1 1 calc R . .
C7 C 0.2812(2) 0.7790(2) 0.20494(17) 0.0191(4) Uani 1 1 d . . .
H7 H 0.3246 0.8210 0.1378 0.023 Uiso 1 1 calc R . .
C9 C 0.0207(2) 0.6436(2) 0.29037(17) 0.0186(4) Uani 1 1 d . . .
H9 H -0.1126 0.5921 0.2816 0.022 Uiso 1 1 calc R . .
C5 C 0.3508(2) 0.7349(2) 0.41660(16) 0.0159(4) Uani 1 1 d . . .
C3 C 0.6755(2) 0.7877(2) 0.55083(17) 0.0175(4) Uani 1 1 d . . .
H3 H 0.7228 0.7943 0.4782 0.021 Uiso 1 1 calc R . .
C11 C -0.2376(3) 0.6031(3) 0.05528(18) 0.0245(4) Uani 1 1 d . . .
H11A H -0.2806 0.4726 0.0593 0.037 Uiso 1 1 calc R . .
H11B H -0.3064 0.5945 -0.0328 0.037 Uiso 1 1 calc R . .
H11C H -0.2652 0.6818 0.1241 0.037 Uiso 1 1 calc R . .
F2 F 0.50113(13) 0.81441(14) 0.86410(9) 0.0203(2) Uani 1 1 d . . .
C8 C 0.0846(2) 0.7020(2) 0.19132(17) 0.0178(4) Uani 1 1 d . . .
B1 B 0.5234(3) 0.7125(3) 0.75383(19) 0.0169(4) Uani 1 1 d . . .
C4 C 0.4871(2) 0.7505(2) 0.53650(17) 0.0159(4) Uani 1 1 d . . .
C2 C 0.7955(2) 0.8153(2) 0.67295(17) 0.0163(4) Uani 1 1 d . . .
O2 O 0.41663(16) 0.72854(17) 0.63376(11) 0.0181(3) Uani 1 1 d . . .
O1 O 0.73540(16) 0.79640(17) 0.77291(11) 0.0181(3) Uani 1 1 d . . .
C10 C 0.1550(2) 0.6619(2) 0.40252(17) 0.0172(4) Uani 1 1 d . . .
H10 H 0.1122 0.6237 0.4710 0.021 Uiso 1 1 calc R . .
C1 C 1.1232(3) 0.8886(3) 0.86388(18) 0.0228(4) Uani 1 1 d . . .
H1A H 1.1049 0.9859 0.9255 0.034 Uiso 1 1 calc R . .
H1B H 1.2610 0.9231 0.8883 0.034 Uiso 1 1 calc R . .
H1C H 1.0503 0.7610 0.8689 0.034 Uiso 1 1 calc R . .

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

# MOLECULAR GEOMETRY
_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
S1 C2 1.7316(17) . ?
S1 C1 1.8038(18) . ?
F1 B1 1.380(2) . ?
O3 C8 1.362(2) . ?
O3 C11 1.439(2) . ?
C6 C7 1.376(2) . ?
C6 C5 1.401(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(2) . ?
C7 H7 0.9500 . ?
C9 C8 1.390(2) . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C5 C10 1.393(2) . ?
C5 C4 1.470(2) . ?
C3 C4 1.377(2) . ?
C3 C2 1.389(2) . ?
C3 H3 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
F2 B1 1.372(2) . ?
B1 O2 1.479(2) . ?
B1 O1 1.498(2) . ?
C4 O2 1.316(2) . ?
C2 O1 1.297(2) . ?
C10 H10 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
C2 S1 C1 101.90(8) . . ?
C8 O3 C11 117.41(13) . . ?
C7 C6 C5 120.86(16) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.88(16) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C8 C9 C10 119.00(16) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C10 C5 C6 118.47(15) . . ?
C10 C5 C4 119.50(15) . . ?
C6 C5 C4 122.03(15) . . ?
C4 C3 C2 119.11(15) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C8 C9 124.33(16) . . ?
O3 C8 C7 115.33(15) . . ?
C9 C8 C7 120.33(15) . . ?
F2 B1 F1 111.10(14) . . ?
F2 B1 O2 109.27(14) . . ?
F1 B1 O2 109.39(14) . . ?
F2 B1 O1 107.85(14) . . ?
F1 B1 O1 108.15(13) . . ?
O2 B1 O1 111.07(13) . . ?
O2 C4 C3 120.89(15) . . ?
O2 C4 C5 114.72(15) . . ?
C3 C4 C5 124.38(15) . . ?
O1 C2 C3 122.96(15) . . ?
O1 C2 S1 117.55(12) . . ?
C3 C2 S1 119.48(13) . . ?
C4 O2 B1 121.99(13) . . ?
C2 O1 B1 120.08(13) . . ?
C9 C10 C5 121.44(16) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

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
C5 C6 C7 C8 -0.8(3) . . . . ?
C7 C6 C5 C10 -0.4(2) . . . . ?
C7 C6 C5 C4 -179.52(15) . . . . ?
C11 O3 C8 C9 -4.3(2) . . . . ?
C11 O3 C8 C7 176.40(14) . . . . ?
C10 C9 C8 O3 -179.73(15) . . . . ?
C10 C9 C8 C7 -0.4(2) . . . . ?
C6 C7 C8 O3 -179.42(14) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C2 C3 C4 O2 -4.4(2) . . . . ?
C2 C3 C4 C5 174.62(15) . . . . ?
C10 C5 C4 O2 -12.8(2) . . . . ?
C6 C5 C4 O2 166.37(15) . . . . ?
C10 C5 C4 C3 168.12(16) . . . . ?
C6 C5 C4 C3 -12.7(3) . . . . ?
C4 C3 C2 O1 4.2(2) . . . . ?
C4 C3 C2 S1 -174.88(12) . . . . ?
C1 S1 C2 O1 2.95(15) . . . . ?
C1 S1 C2 C3 -177.91(13) . . . . ?
C3 C4 O2 B1 -9.5(2) . . . . ?
C5 C4 O2 B1 171.34(14) . . . . ?
F2 B1 O2 C4 140.12(15) . . . . ?
F1 B1 O2 C4 -98.05(17) . . . . ?
O1 B1 O2 C4 21.3(2) . . . . ?
C3 C2 O1 B1 9.7(2) . . . . ?
S1 C2 O1 B1 -171.20(11) . . . . ?
F2 B1 O1 C2 -140.81(14) . . . . ?
F1 B1 O1 C2 98.95(16) . . . . ?
O2 B1 O1 C2 -21.1(2) . . . . ?
C8 C9 C10 C5 -0.8(2) . . . . ?
C6 C5 C10 C9 1.2(2) . . . . ?
C4 C5 C10 C9 -179.64(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
# End of CIF  ============================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_chemical_properties_physical    ', Stable'
_exptl_crystal_preparation       ', Luminescent'
