# Electronic Supplementary Material (ESI) for ChemComm.
# 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_4e
_database_code_depnum_ccdc_archive 'CCDC 1440630'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
# 2097GuillotICMMO
# Terry Tomakinian / Guillaume Vincent MSMT-1 TT812-3 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H13 F3 N2 O'
_chemical_formula_sum            'C16 H13 F3 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       bloc
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         306.28

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.4475(4)
_cell_length_b                   12.1951(11)
_cell_length_c                   12.2971(10)
_cell_angle_alpha                114.682(2)
_cell_angle_beta                 98.556(2)
_cell_angle_gamma                98.672(2)
_cell_volume                     713.13(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3388
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      31.56
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source_type              'kappa X8 APEX II Bruker ICMMO'
_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            9568
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.875
_diffrn_reflns_theta_max         31.728
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.801
_diffrn_measured_fraction_theta_full 0.941
_reflns_number_total             3862
_reflns_number_gt                3003
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0532P)²+0.3534P] 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_number_reflns         3862
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
H100 H -0.361(4) 0.016(2) 0.362(2) 0.045(6) Uiso 1 1 d . . . . .
H101 H -0.419(4) -0.116(2) 0.285(2) 0.039(6) Uiso 1 1 d . . . . .
F2 F 0.7925(2) 0.37287(11) 0.22406(11) 0.0440(3) Uani 1 1 d . . . . .
F3 F 0.4228(2) 0.36997(11) 0.13487(11) 0.0470(3) Uani 1 1 d . . . . .
F1 F 0.5936(3) 0.50828(10) 0.32034(11) 0.0559(4) Uani 1 1 d . . . . .
O2 O 0.0487(2) -0.09396(10) 0.10623(9) 0.0212(2) Uani 1 1 d . . . . .
N2 N -0.3030(2) -0.05293(15) 0.34360(12) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.1284(2) 0.05803(12) 0.41123(10) 0.0197(3) Uani 1 1 d . . . . .
H1A H 0.1587 0.0612 0.4833 0.024 Uiso 1 1 calc R U . . .
C6 C 0.0116(3) -0.16319(14) 0.25333(12) 0.0175(3) Uani 1 1 d . . . . .
C7 C -0.0631(2) -0.04040(14) 0.30563(12) 0.0167(3) Uani 1 1 d . . . . .
C10 C 0.1523(3) 0.12078(13) 0.26070(12) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.4433(3) 0.30347(14) 0.29054(14) 0.0238(3) Uani 1 1 d . . . . .
C11 C 0.2543(3) 0.14478(13) 0.38266(12) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.2432(3) 0.20051(14) 0.21466(13) 0.0210(3) Uani 1 1 d . . . . .
H15 H 0.1725 0.1858 0.1348 0.025 Uiso 1 1 calc R U . . .
C2 C 0.1704(3) -0.28592(15) 0.07744(14) 0.0254(3) Uani 1 1 d . . . . .
H2 H 0.2166 -0.2979 0.0042 0.031 Uiso 1 1 calc R U . . .
C8 C -0.0483(3) 0.00105(14) 0.19882(12) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.0787(3) -0.18355(14) 0.14307(12) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.5478(3) 0.32607(15) 0.41132(14) 0.0269(3) Uani 1 1 d . . . . .
H13 H 0.6819 0.3950 0.4606 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0271(3) -0.24906(15) 0.29924(13) 0.0232(3) Uani 1 1 d . . . . .
H5 H -0.0220 -0.2375 0.3718 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5600(4) 0.38808(15) 0.24322(15) 0.0293(4) Uani 1 1 d . . . . .
C4 C 0.1173(3) -0.35281(15) 0.23463(15) 0.0278(3) Uani 1 1 d . . . . .
H4 H 0.1290 -0.4111 0.2643 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4545(3) 0.24743(15) 0.45863(13) 0.0242(3) Uani 1 1 d . . . . .
H12 H 0.5239 0.2628 0.5389 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1903(3) -0.36991(15) 0.12578(15) 0.0290(3) Uani 1 1 d . . . . .
H3 H 0.2536 -0.4388 0.0846 0.035 Uiso 1 1 calc R U . . .
C9 C -0.2988(3) 0.00678(17) 0.13208(14) 0.0276(3) Uani 1 1 d . . . . .
H9A H -0.2706 0.0282 0.0674 0.041 Uiso 1 1 calc R U . . .
H9B H -0.3677 0.0685 0.1890 0.041 Uiso 1 1 calc R U . . .
H9C H -0.4171 -0.0727 0.0974 0.041 Uiso 1 1 calc R U . . .


_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
F2 C16 1.348(2) . ?
F3 C16 1.338(2) . ?
F1 C16 1.3372(19) . ?
O2 C1 1.3679(17) . ?
O2 C8 1.4762(16) . ?
N2 C7 1.4596(17) . ?
N1 C11 1.3697(19) . ?
N1 C7 1.4604(19) . ?
C6 C1 1.3881(18) . ?
C6 C5 1.3888(19) . ?
C6 C7 1.5096(19) . ?
C7 C8 1.6002(18) . ?
C10 C15 1.382(2) . ?
C10 C11 1.4072(18) . ?
C10 C8 1.499(2) . ?
C14 C15 1.393(2) . ?
C14 C13 1.402(2) . ?
C14 C16 1.490(2) . ?
C11 C12 1.392(2) . ?
C2 C1 1.388(2) . ?
C2 C3 1.392(2) . ?
C8 C9 1.5113(19) . ?
C13 C12 1.387(2) . ?
C5 C4 1.392(2) . ?
C4 C3 1.394(2) . ?

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
C1 O2 C8 108.59(10) . . ?
C11 N1 C7 112.42(11) . . ?
C1 C6 C5 119.93(13) . . ?
C1 C6 C7 109.30(12) . . ?
C5 C6 C7 130.74(12) . . ?
N2 C7 N1 107.77(11) . . ?
N2 C7 C6 111.05(12) . . ?
N1 C7 C6 113.83(10) . . ?
N2 C7 C8 119.16(10) . . ?
N1 C7 C8 103.27(11) . . ?
C6 C7 C8 101.71(10) . . ?
C15 C10 C11 120.81(14) . . ?
C15 C10 C8 130.05(12) . . ?
C11 C10 C8 109.11(12) . . ?
C15 C14 C13 120.57(14) . . ?
C15 C14 C16 120.85(14) . . ?
C13 C14 C16 118.51(15) . . ?
N1 C11 C12 127.98(13) . . ?
N1 C11 C10 111.26(13) . . ?
C12 C11 C10 120.75(13) . . ?
C10 C15 C14 118.55(13) . . ?
C1 C2 C3 117.25(13) . . ?
O2 C8 C10 108.96(10) . . ?
O2 C8 C9 106.71(11) . . ?
C10 C8 C9 115.02(12) . . ?
O2 C8 C7 105.92(10) . . ?
C10 C8 C7 103.75(10) . . ?
C9 C8 C7 116.02(11) . . ?
O2 C1 C2 123.48(12) . . ?
O2 C1 C6 114.26(12) . . ?
C2 C1 C6 122.26(13) . . ?
C12 C13 C14 121.12(15) . . ?
C6 C5 C4 118.79(13) . . ?
F1 C16 F3 106.49(14) . . ?
F1 C16 F2 105.86(15) . . ?
F3 C16 F2 105.12(13) . . ?
F1 C16 C14 113.10(13) . . ?
F3 C16 C14 113.38(15) . . ?
F2 C16 C14 112.23(13) . . ?
C5 C4 C3 120.42(14) . . ?
C13 C12 C11 118.17(13) . . ?
C2 C3 C4 121.31(14) . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4


_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1440631'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
# 2258GuillotICMMO
# Terry MSMT1   TT1221-2 plate

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H18 N2 O5 S2'
_chemical_formula_sum            'C17 H18 N2 O5 S2'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         394.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.2208(2)
_cell_length_b                   9.2881(2)
_cell_length_c                   11.3189(3)
_cell_angle_alpha                92.7550(10)
_cell_angle_beta                 107.1930(10)
_cell_angle_gamma                106.5060(10)
_cell_volume                     878.64(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      35.00
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.335
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9247
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         '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            25778
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         35.133
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7430
_reflns_number_gt                6257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0489P)²+0.2610P] 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_number_reflns         7430
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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
C1 C -0.11333(11) 0.22178(10) -0.22889(9) 0.01112(15) Uani 1 1 d . . . . .
C2 C -0.27465(11) 0.19223(12) -0.24110(10) 0.01461(17) Uani 1 1 d . . . . .
H2 H -0.3170 0.1433 -0.1833 0.018 Uiso 1 1 calc R U . . .
C3 C -0.37025(12) 0.23832(12) -0.34258(10) 0.01718(19) Uani 1 1 d . . . . .
H3 H -0.4782 0.2189 -0.3527 0.021 Uiso 1 1 calc R U . . .
C4 C -0.30789(12) 0.31300(12) -0.42942(10) 0.01687(18) Uani 1 1 d . . . . .
H4 H -0.3733 0.3450 -0.4953 0.020 Uiso 1 1 calc R U . . .
C5 C -0.14678(11) 0.33953(11) -0.41699(9) 0.01370(16) Uani 1 1 d . . . . .
H5 H -0.1042 0.3885 -0.4746 0.016 Uiso 1 1 calc R U . . .
C6 C -0.05144(11) 0.29199(11) -0.31772(9) 0.01131(15) Uani 1 1 d . . . . .
C7 C 0.11946(11) 0.29613(11) -0.28828(9) 0.01060(15) Uani 1 1 d . . . . .
C8 C 0.23668(12) 0.44394(12) -0.29644(10) 0.01514(17) Uani 1 1 d . . . . .
H8A H 0.3429 0.4364 -0.2697 0.023 Uiso 1 1 calc R U . . .
H8B H 0.2314 0.5249 -0.2436 0.023 Uiso 1 1 calc R U . . .
H8C H 0.2101 0.4642 -0.3813 0.023 Uiso 1 1 calc R U . . .
C9 C 0.19177(11) 0.08076(11) -0.31043(9) 0.01227(16) Uani 1 1 d . . . . .
C10 C 0.23576(12) -0.03177(12) -0.36246(10) 0.01532(17) Uani 1 1 d . . . . .
H10 H 0.2213 -0.0466 -0.4475 0.018 Uiso 1 1 calc R U . . .
C11 C 0.30272(13) -0.12189(12) -0.28142(11) 0.01751(18) Uani 1 1 d . . . . .
H11 H 0.3343 -0.1978 -0.3132 0.021 Uiso 1 1 calc R U . . .
C12 C 0.32320(13) -0.10055(12) -0.15399(10) 0.01825(19) Uani 1 1 d . . . . .
H12 H 0.3670 -0.1627 -0.1022 0.022 Uiso 1 1 calc R U . . .
C13 C 0.27832(12) 0.01365(12) -0.10389(10) 0.01506(17) Uani 1 1 d . . . . .
H13 H 0.2923 0.0290 -0.0189 0.018 Uiso 1 1 calc R U . . .
C14 C 0.21244(11) 0.10375(11) -0.18375(9) 0.01124(15) Uani 1 1 d . . . . .
C15 C 0.15617(10) 0.23529(10) -0.15739(9) 0.00986(15) Uani 1 1 d . . . . .
C16 C 0.16821(11) 0.39995(11) 0.13541(9) 0.01222(16) Uani 1 1 d . . . . .
H16A H 0.0545 0.3531 0.0935 0.015 Uiso 1 1 calc R U . . .
H16B H 0.1811 0.4822 0.1976 0.015 Uiso 1 1 calc R U . . .
C17 C 0.15778(16) 0.24224(15) 0.33373(12) 0.0247(2) Uani 1 1 d . . . . .
H17A H 0.1857 0.1651 0.3805 0.037 Uiso 1 1 calc R U . . .
H17B H 0.0437 0.2139 0.2973 0.037 Uiso 1 1 calc R U . . .
H17C H 0.1959 0.3368 0.3884 0.037 Uiso 1 1 calc R U . . .
N1 N 0.00487(9) 0.19545(10) -0.13048(8) 0.01156(14) Uani 1 1 d . . . . .
N2 N 0.28116(9) 0.34047(9) -0.05182(8) 0.01035(13) Uani 1 1 d . . . . .
O1 O 0.12775(9) 0.17939(9) -0.37709(7) 0.01401(13) Uani 1 1 d . . . . .
O2 O 0.41502(8) 0.57870(8) 0.09021(7) 0.01340(13) Uani 1 1 d . . . . .
O3 O 0.14401(9) 0.54094(9) -0.05536(7) 0.01454(13) Uani 1 1 d . . . . .
O4 O 0.17967(10) 0.12103(9) 0.13078(8) 0.01956(15) Uani 1 1 d . . . . .
O5 O 0.41603(9) 0.32337(10) 0.26889(9) 0.02406(18) Uani 1 1 d . . . . .
S1 S 0.25681(3) 0.47890(3) 0.02316(2) 0.00973(5) Uani 1 1 d . . . . .
S2 S 0.24573(3) 0.26226(3) 0.21455(2) 0.01315(6) Uani 1 1 d . . . . .
H100 H -0.021(2) 0.113(2) -0.1055(15) 0.027(4) Uiso 1 1 d . . . . .
H200 H 0.372(2) 0.357(2) -0.0524(17) 0.035(5) 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
C1 N1 1.3958(12) . ?
C1 C2 1.3964(13) . ?
C1 C6 1.3973(13) . ?
C2 C3 1.3938(15) . ?
C3 C4 1.3968(16) . ?
C4 C5 1.3973(14) . ?
C5 C6 1.3837(13) . ?
C6 C7 1.4999(13) . ?
C7 O1 1.4763(12) . ?
C7 C8 1.5132(13) . ?
C7 C15 1.5879(13) . ?
C9 O1 1.3666(12) . ?
C9 C14 1.3870(13) . ?
C9 C10 1.3881(14) . ?
C10 C11 1.3985(15) . ?
C11 C12 1.3949(16) . ?
C12 C13 1.3957(14) . ?
C13 C14 1.3869(14) . ?
C14 C15 1.5059(13) . ?
C15 N2 1.4644(12) . ?
C15 N1 1.4645(12) . ?
C16 S1 1.7839(10) . ?
C16 S2 1.7888(10) . ?
C17 S2 1.7599(12) . ?
N2 S1 1.6111(8) . ?
O2 S1 1.4397(7) . ?
O3 S1 1.4308(8) . ?
O4 S2 1.4407(8) . ?
O5 S2 1.4336(8) . ?

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
N1 C1 C2 127.22(9) . . ?
N1 C1 C6 112.00(8) . . ?
C2 C1 C6 120.71(9) . . ?
C3 C2 C1 117.92(9) . . ?
C2 C3 C4 121.61(9) . . ?
C3 C4 C5 119.75(10) . . ?
C6 C5 C4 119.08(9) . . ?
C5 C6 C1 120.87(9) . . ?
C5 C6 C7 129.70(9) . . ?
C1 C6 C7 109.36(8) . . ?
O1 C7 C6 108.66(7) . . ?
O1 C7 C8 106.25(7) . . ?
C6 C7 C8 116.52(8) . . ?
O1 C7 C15 105.27(7) . . ?
C6 C7 C15 103.04(7) . . ?
C8 C7 C15 116.43(8) . . ?
O1 C9 C14 114.14(8) . . ?
O1 C9 C10 123.89(9) . . ?
C14 C9 C10 121.96(9) . . ?
C9 C10 C11 117.12(9) . . ?
C12 C11 C10 121.48(9) . . ?
C11 C12 C13 120.30(10) . . ?
C14 C13 C12 118.46(9) . . ?
C13 C14 C9 120.69(9) . . ?
C13 C14 C15 130.57(9) . . ?
C9 C14 C15 108.74(8) . . ?
N2 C15 N1 109.08(7) . . ?
N2 C15 C14 108.33(7) . . ?
N1 C15 C14 115.50(8) . . ?
N2 C15 C7 116.52(7) . . ?
N1 C15 C7 105.33(7) . . ?
C14 C15 C7 102.22(7) . . ?
S1 C16 S2 116.05(5) . . ?
C1 N1 C15 109.68(8) . . ?
C15 N2 S1 124.29(6) . . ?
C9 O1 C7 108.35(7) . . ?
O3 S1 O2 118.64(5) . . ?
O3 S1 N2 112.18(4) . . ?
O2 S1 N2 105.87(4) . . ?
O3 S1 C16 105.35(4) . . ?
O2 S1 C16 107.74(5) . . ?
N2 S1 C16 106.40(4) . . ?
O5 S2 O4 118.49(6) . . ?
O5 S2 C17 109.58(6) . . ?
O4 S2 C17 108.00(6) . . ?
O5 S2 C16 109.84(5) . . ?
O4 S2 C16 108.03(5) . . ?
C17 S2 C16 101.54(6) . . ?

_refine_diff_density_max         0.592
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4


_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_11a
_database_code_depnum_ccdc_archive 'CCDC 1440632'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-03-15 downloaded from the CCDC.
;
# v143guillotICMMO
# Terry MSMT1 TT956

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H16 B F2 N O'
_chemical_formula_sum            'C18 H16 B F2 N O'
_chemical_melting_point          ?

_exptl_crystal_description       bloc
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         311.13

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   13.5204(7)
_cell_length_b                   12.9163(7)
_cell_length_c                   17.2730(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3016.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9145
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      30.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            192577
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.479
_diffrn_reflns_theta_max         30.613
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4636
_reflns_number_gt                3853
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0885P)²+5.2044P] 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_number_reflns         4636
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1892
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_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
C1 C 0.18059(14) 1.19189(14) 0.15141(11) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.11544(14) 1.12036(14) 0.12124(11) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.07222(14) 1.13103(15) 0.04963(12) 0.0198(4) Uani 1 1 d . . . . .
H3 H 0.0285 1.0815 0.0307 0.024 Uiso 1 1 calc R U . . .
C4 C 0.09598(16) 1.21796(16) 0.00660(11) 0.0222(4) Uani 1 1 d . . . . .
H4 H 0.0681 1.2275 -0.0421 0.027 Uiso 1 1 calc R U . . .
C5 C 0.16281(16) 1.29258(16) 0.03663(12) 0.0249(4) Uani 1 1 d . . . . .
H5 H 0.1783 1.3511 0.0077 0.030 Uiso 1 1 calc R U . . .
C6 C 0.20546(14) 1.27830(14) 0.10969(11) 0.0190(4) Uani 1 1 d . . . . .
H6 H 0.2498 1.3265 0.1295 0.023 Uiso 1 1 calc R U . . .
C7 C 0.15134(14) 0.98470(14) 0.30129(11) 0.0164(3) Uani 1 1 d . . . . .
C8 C 0.08344(13) 0.90113(14) 0.29788(11) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.07329(16) 0.83497(16) 0.36041(12) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.0276 0.7812 0.3581 0.028 Uiso 1 1 calc R U . . .
C10 C 0.12929(16) 0.84755(16) 0.42535(12) 0.0245(4) Uani 1 1 d . . . . .
H10 H 0.1214 0.8025 0.4669 0.029 Uiso 1 1 calc R U . . .
C11 C 0.19792(15) 0.92701(16) 0.42999(11) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.2364 0.9337 0.4743 0.026 Uiso 1 1 calc R U . . .
C12 C 0.21005(14) 0.99569(15) 0.37052(11) 0.0185(4) Uani 1 1 d . . . . .
H12 H 0.2558 1.0491 0.3747 0.022 Uiso 1 1 calc R U . . .
C13 C 0.15650(13) 1.05564(13) 0.23794(10) 0.0150(3) Uani 1 1 d . . . . .
C14 C 0.21350(13) 1.15686(14) 0.23113(11) 0.0157(3) Uani 1 1 d . . . . .
C15 C 0.17943(14) 1.23384(14) 0.29442(11) 0.0185(4) Uani 1 1 d . . . . .
H15A H 0.2077 1.3007 0.2845 0.028 Uiso 1 1 calc R U . . .
H15B H 0.2009 1.2096 0.3442 0.028 Uiso 1 1 calc R U . . .
H15C H 0.1086 1.2389 0.2938 0.028 Uiso 1 1 calc R U . . .
C16 C 0.32777(13) 1.14195(14) 0.23489(11) 0.0173(3) Uani 1 1 d . . . . .
H16A H 0.3595 1.2072 0.2223 0.021 Uiso 1 1 calc R U . . .
H16B H 0.3461 1.1242 0.2875 0.021 Uiso 1 1 calc R U . . .
C17 C 0.36633(14) 1.06015(15) 0.18153(12) 0.0197(4) Uani 1 1 d . . . . .
H17 H 0.3506 0.9915 0.1922 0.024 Uiso 1 1 calc R U . . .
C18 C 0.42133(16) 1.07978(19) 0.12018(13) 0.0276(4) Uani 1 1 d . . . . .
H18A H 0.4382 1.1477 0.1081 0.033 Uiso 1 1 calc R U . . .
H18B H 0.4432 1.0257 0.0890 0.033 Uiso 1 1 calc R U . . .
B1 B 0.03392(16) 0.94263(17) 0.16279(13) 0.0193(4) Uani 1 1 d . . . . .
N1 N 0.10246(11) 1.03844(12) 0.17635(9) 0.0158(3) Uani 1 1 d . . . . .
O1 O 0.02729(11) 0.88541(11) 0.23520(9) 0.0237(3) Uani 1 1 d . . . . .
F1 F 0.07664(9) 0.88179(9) 0.10584(7) 0.0235(3) Uani 1 1 d . . . . .
F2 F -0.05803(9) 0.97450(10) 0.14059(8) 0.0253(3) 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
C1 C6 1.370(3) . ?
C1 C2 1.379(3) . ?
C1 C14 1.516(3) . ?
C2 C3 1.375(3) . ?
C2 N1 1.434(2) . ?
C3 C4 1.384(3) . ?
C4 C5 1.419(3) . ?
C5 C6 1.400(3) . ?
C7 C8 1.418(3) . ?
C7 C13 1.429(2) . ?
C7 C12 1.442(3) . ?
C8 O1 1.338(2) . ?
C8 C9 1.384(3) . ?
C9 C10 1.363(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.367(3) . ?
C13 N1 1.310(2) . ?
C13 C14 1.522(2) . ?
C14 C15 1.548(2) . ?
C14 C16 1.558(3) . ?
C16 C17 1.496(3) . ?
C17 C18 1.319(3) . ?
B1 F2 1.364(2) . ?
B1 F1 1.385(2) . ?
B1 O1 1.456(3) . ?
B1 N1 1.564(3) . ?

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
C6 C1 C2 120.25(18) . . ?
C6 C1 C14 130.43(18) . . ?
C2 C1 C14 109.31(16) . . ?
C3 C2 C1 122.98(18) . . ?
C3 C2 N1 128.25(17) . . ?
C1 C2 N1 108.77(16) . . ?
C2 C3 C4 117.75(19) . . ?
C3 C4 C5 120.16(18) . . ?
C6 C5 C4 120.16(18) . . ?
C1 C6 C5 118.70(18) . . ?
C8 C7 C13 119.20(17) . . ?
C8 C7 C12 117.75(16) . . ?
C13 C7 C12 123.02(17) . . ?
O1 C8 C9 118.78(17) . . ?
O1 C8 C7 121.10(17) . . ?
C9 C8 C7 120.11(18) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 C11 120.52(19) . . ?
C12 C11 C10 121.15(19) . . ?
C11 C12 C7 119.54(18) . . ?
N1 C13 C7 119.09(16) . . ?
N1 C13 C14 111.43(16) . . ?
C7 C13 C14 129.39(16) . . ?
C1 C14 C13 100.25(14) . . ?
C1 C14 C15 111.25(15) . . ?
C13 C14 C15 110.27(15) . . ?
C1 C14 C16 111.45(16) . . ?
C13 C14 C16 113.11(15) . . ?
C15 C14 C16 110.18(15) . . ?
C17 C16 C14 114.03(15) . . ?
C18 C17 C16 123.75(19) . . ?
F2 B1 F1 110.58(17) . . ?
F2 B1 O1 109.79(17) . . ?
F1 B1 O1 110.35(17) . . ?
F2 B1 N1 110.08(16) . . ?
F1 B1 N1 107.95(16) . . ?
O1 B1 N1 108.04(16) . . ?
C13 N1 C2 110.23(15) . . ?
C13 N1 B1 125.91(17) . . ?
C2 N1 B1 123.85(16) . . ?
C8 O1 B1 125.69(15) . . ?

_refine_diff_density_max         1.143
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4


_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P b c a'
_symmetry_int_tables_number      61
_chemical_absolute_configuration .

