# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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__119849_4
_database_code_depnum_ccdc_archive 'CCDC 1854624'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;

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

# CHEMICAL DATA

_chemical_formula_sum            'C18 H14 B F2 N O2 '
_chemical_formula_moiety         'C18 H14 B F2 N O2 '
_chemical_formula_weight         325.12
_chemical_melting_point          ?

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

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z

#------------------------------------------------------------------------------

_cell_length_a                   7.7350(3)
_cell_length_b                   17.5816(7)
_cell_length_c                   11.0299(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.364(2)
_cell_angle_gamma                90.0000
_cell_volume                     1480.01(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3475
_cell_measurement_theta_min      6.5
_cell_measurement_theta_max      71.4
_cell_measurement_temperature    174.1

#------------------------------------------------------------------------------

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672.00
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  0.851

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

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            17052
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_theta_max         71.62
_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        71.62
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

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

# REFINEMENT DATA

_refine_special_details          
;
    Refinement using reflections with F² > 2.0 sigma(F²).
    The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are 
    based on F, with F set to zero for negative F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2855
_reflns_number_gt                8513
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.0665
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         8564
_refine_ls_number_parameters     231
_refine_ls_goodness_of_fit_ref   6.953
_refine_ls_weighting_scheme      unit
_refine_ls_weighting_details     'w = 1.0'
_refine_ls_shift/su_max          0.0000
_refine_diff_density_max         4.22
_refine_diff_density_min         -4.25
_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 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
B B 0.009 0.004
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.073 0.053
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F(1) F 0.6608(2) 0.16116(10) 0.21984(14) 0.0508(6) Uani 1.00 1 d . . .
F(2) F 0.4411(2) 0.14577(9) 0.33530(16) 0.0515(6) Uani 1.00 1 d . . .
O(3) O 1.1721(2) 0.05102(12) 0.95600(19) 0.0419(7) Uani 1.00 1 d . . .
O(4) O 0.5635(2) 0.04003(12) 0.25162(18) 0.0390(7) Uani 1.00 1 d . . .
N(5) N 0.7349(2) 0.11079(14) 0.4247(2) 0.0274(8) Uani 1.00 1 d . . .
C(6) C 1.0799(4) 0.0550(2) 0.8413(2) 0.0303(11) Uani 1.00 1 d . . .
C(7) C 0.9496(3) 0.11627(18) 0.6533(2) 0.0285(11) Uani 1.00 1 d . . .
C(8) C 0.8719(3) 0.04645(18) 0.6084(2) 0.0273(10) Uani 1.00 1 d . . .
C(9) C 0.5029(3) -0.09189(19) 0.2596(2) 0.0300(11) Uani 1.00 1 d . . .
C(10) C 0.6755(3) -0.02127(17) 0.4366(2) 0.0287(10) Uani 1.00 1 d . . .
C(11) C 1.0526(3) 0.11939(18) 0.7710(2) 0.0330(11) Uani 1.00 1 d . . .
C(12) C 0.9063(3) -0.01947(17) 0.6830(2) 0.0320(10) Uani 1.00 1 d . . .
C(13) C 0.9214(4) 0.18162(18) 0.5767(2) 0.0387(11) Uani 1.00 1 d . . .
C(14) C 1.0084(3) -0.01454(18) 0.7948(2) 0.0359(11) Uani 1.00 1 d . . .
C(15) C 0.7616(3) 0.04560(19) 0.4908(2) 0.0266(10) Uani 1.00 1 d . . .
C(16) C 0.8182(4) 0.17688(18) 0.4673(2) 0.0375(11) Uani 1.00 1 d . . .
C(17) C 0.3401(4) -0.2188(2) 0.1417(3) 0.0483(13) Uani 1.00 1 d . . .
C(18) C 0.5855(3) -0.02258(19) 0.3205(2) 0.0299(10) Uani 1.00 1 d . . .
C(19) C 0.3195(4) -0.1487(2) 0.0866(2) 0.0481(13) Uani 1.00 1 d . . .
C(20) C 0.4003(4) -0.08587(19) 0.1447(2) 0.0385(11) Uani 1.00 1 d . . .
C(21) C 1.2375(4) 0.12064(17) 1.0120(2) 0.0503(12) Uani 1.00 1 d . . .
C(22) C 0.4424(4) -0.22636(19) 0.2551(3) 0.0526(13) Uani 1.00 1 d . . .
C(23) C 0.5238(4) -0.1636(2) 0.3138(2) 0.0462(12) Uani 1.00 1 d . . .
B(24) B 0.5964(5) 0.1165(2) 0.3022(3) 0.0393(14) Uani 1.00 1 d . . .
H(1) H 0.6829 -0.0667 0.4837 0.034 Uiso 1.00 1 c R . .
H(2) H 1.1015 0.1663 0.8026 0.039 Uiso 1.00 1 c R . .
H(3) H 0.8567 -0.0667 0.6531 0.037 Uiso 1.00 1 c R . .
H(4) H 0.9752 0.2286 0.6035 0.045 Uiso 1.00 1 c R . .
H(5) H 1.0331 -0.0597 0.8417 0.042 Uiso 1.00 1 c R . .
H(6) H 0.8001 0.2212 0.4176 0.044 Uiso 1.00 1 c R . .
H(7) H 0.2818 -0.2617 0.1019 0.058 Uiso 1.00 1 c R . .
H(8) H 0.2525 -0.1437 0.0069 0.056 Uiso 1.00 1 c R . .
H(9) H 0.3839 -0.0372 0.1074 0.045 Uiso 1.00 1 c R . .
H(10) H 0.4579 -0.2752 0.2923 0.062 Uiso 1.00 1 c R . .
H(11) H 0.5949 -0.1691 0.3921 0.054 Uiso 1.00 1 c R . .
H(12) H 1.3510 0.1288 0.9922 0.058 Uiso 1.00 1 c R . .
H(13) H 1.2441 0.1198 1.0988 0.058 Uiso 1.00 1 c R . .
H(14) H 1.1616 0.1605 0.9784 0.058 Uiso 1.00 1 c R . .



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

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  CRYSTALS
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_molecular_graphics    ?

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

# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;



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

# 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

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

####################################################################### 
# 
# 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__120462_1
_database_code_depnum_ccdc_archive 'CCDC 1854625'
_audit_update_record             
;
2018-07-09 deposited with the CCDC.
2018-11-09 downloaded from the CCDC.
;

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

# CHEMICAL DATA

_chemical_formula_sum            'C17 H16 B F2 N O3 S '
_chemical_formula_moiety         'C17 H16 B F2 N O3 S '
_chemical_formula_weight         363.19
_chemical_melting_point          ?

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

# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z

#------------------------------------------------------------------------------

_cell_length_a                   12.1184(6)
_cell_length_b                   8.1766(4)
_cell_length_c                   16.5924(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.697(3)
_cell_angle_gamma                90.0000
_cell_volume                     1640.68(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3677
_cell_measurement_theta_min      6.5
_cell_measurement_theta_max      71.2
_cell_measurement_temperature    293.1

#------------------------------------------------------------------------------

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752.00
_exptl_absorpt_coefficient_mu    2.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_absorpt_correction_T_min  0.457
_exptl_absorpt_correction_T_max  0.637

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

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_reflns_number            18565
_diffrn_reflns_av_R_equivalents  0.086
_diffrn_reflns_theta_max         71.64
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        71.64
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

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

# REFINEMENT DATA

_refine_special_details          
;
    Refinement using reflections with F² > 2.0 sigma(F²).
    The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are 
    based on F, with F set to zero for negative F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3134
_reflns_number_gt                8927
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.1597
_refine_ls_wR_factor_ref         0.1982
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         8999
_refine_ls_number_parameters     230
_refine_ls_goodness_of_fit_ref   3.595
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     'w = 1/σ²(Fo)'
_refine_ls_shift/su_max          0.1007
_refine_diff_density_max         9.94
_refine_diff_density_min         -20.10
_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 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
B B 0.009 0.004
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.073 0.053
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.333 0.557
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S(1) S 0.6166(2) 0.8890(2) 0.55589(12) 0.1653(12) Uani 1.00 1 d . . .
F(3) F 0.6162(2) 0.3025(4) 0.38034(17) 0.0900(14) Uani 1.00 1 d . . .
F(4) F 0.6443(2) 0.4273(3) 0.26232(19) 0.0835(13) Uani 1.00 1 d . . .
O(5) O 0.0584(3) 0.6984(4) 0.4777(2) 0.0789(17) Uani 1.00 1 d . . .
O(6) O 0.6492(3) 0.5815(5) 0.3796(2) 0.0720(18) Uani 1.00 1 d . . .
O(7) O -0.0405(4) 0.6427(4) 0.3386(2) 0.0794(19) Uani 1.00 1 d . . .
N(1) N 0.4729(5) 0.4746(7) 0.3238(3) 0.062(2) Uani 1.00 1 d . . .
C(1) C 0.7922(2) 0.7797(3) 0.47815(16) . Uani 1.00 1 d . . .
C(9) C 0.4234(6) 0.5669(9) 0.3787(6) 0.072(3) Uani 1.00 1 d . . .
C(10) C 0.6721(5) 0.7701(6) 0.4858(3) 0.0523 Uiso 1.00 1 d . . .
C(11) C 0.3068(7) 0.5702(6) 0.3656(3) 0.056(2) Uani 1.00 1 d . . .
C(12) C 0.3136(5) 0.4630(6) 0.2255(3) 0.071(2) Uani 1.00 1 d . . .
C(13) C 0.1271(5) 0.5612(6) 0.2817(4) 0.061(2) Uani 1.00 1 d . . .
C(14) C 0.2427(7) 0.5367(6) 0.2941(4) 0.057(2) Uani 1.00 1 d . . .
C(15) C 0.4144(5) 0.3771(7) 0.2582(3) 0.071(2) Uani 1.00 1 d . . .
C(16) C 0.4855(6) 0.6569(7) 0.4351(3) 0.063(2) Uani 1.00 1 d . . .
C(17) C 0.0691(7) 0.6159(7) 0.3396(4) 0.069(3) Uani 1.00 1 d . . .
C(18) C 0.2404(6) 0.6237(5) 0.4264(3) 0.056(2) Uani 1.00 1 d . . .
C(19) C 0.8129(4) 0.8768(7) 0.5345(3) 0.0711 Uiso 1.00 1 d . . .
C(20) C 0.1211(6) 0.6461(7) 0.4142(5) 0.056(2) Uani 1.00 1 d . . .
C(21) C 0.5904(6) 0.6649(7) 0.4335(4) 0.065(2) Uani 1.00 1 d . . .
C(22) C -0.0979(4) 0.5999(6) 0.2645(3) 0.095(3) Uani 1.00 1 d . . .
C(23) C 0.1041(4) 0.7092(6) 0.5594(3) 0.110(3) Uani 1.00 1 d . . .
C(24) C 0.7521(6) 0.9618(5) 0.5848(2) 0.107(2) Uani 1.00 1 d . . .
B(1) B 0.5952(9) 0.4473(11) 0.3331(5) 0.064(4) Uani 1.00 1 d . . .
H(1) H 0.8385 0.7254 0.4426 . Uiso 1.00 1 c R . .
H(2) H 0.0907 0.5305 0.2316 0.073 Uiso 1.00 1 c R . .
H(3) H 0.4478 0.7155 0.4744 0.075 Uiso 1.00 1 c R . .
H(4) H 0.2773 0.6468 0.4774 0.066 Uiso 1.00 1 c R . .
H(5) H 0.8863 0.9141 0.5465 0.086 Uiso 1.00 1 c R . .
H(6) H 0.7613 1.0343 0.6295 0.122 Uiso 1.00 1 c R . .
H(7) H 0.2688 0.3949 0.1905 0.087 Uiso 1.00 1 c R . .
H(8) H 0.3400 0.5527 0.1959 0.086 Uiso 1.00 1 c R . .
H(9) H 0.4619 0.3496 0.2169 0.084 Uiso 1.00 1 c R . .
H(10) H 0.3878 0.2798 0.2815 0.084 Uiso 1.00 1 c R . .
H(11) H -0.1013 0.6909 0.2289 0.113 Uiso 1.00 1 c R . .
H(12) H -0.1708 0.5659 0.2744 0.113 Uiso 1.00 1 c R . .
H(13) H -0.0599 0.5125 0.2407 0.113 Uiso 1.00 1 c R . .
H(14) H 0.0958 0.6060 0.5846 0.133 Uiso 1.00 1 c R . .
H(15) H 0.0692 0.7912 0.5893 0.133 Uiso 1.00 1 c R . .
H(16) H 0.1805 0.7340 0.5577 0.133 Uiso 1.00 1 c R . .



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

_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_solution    SIR92
_computing_structure_refinement  CRYSTALS
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_molecular_graphics    ?

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

# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

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

# 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

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

