# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_P21_c
_database_code_depnum_ccdc_archive 'CCDC 1555080'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2017-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H6 Br F3 O S'
_chemical_formula_weight         287.10

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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.993(7)
_cell_length_b                   3.9406(12)
_cell_length_c                   12.147(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.906(5)
_cell_angle_gamma                90.00
_cell_volume                     999.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    4.328
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3253
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.05
_reflns_number_total             1736
_reflns_number_gt                1426
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0768P)²+1.0967P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1736
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.06037(3) 0.70622(15) 0.68534(5) 0.0457(3) Uani 1 1 d . . .
S1 S 0.28104(7) 0.3049(4) 0.38142(10) 0.0335(4) Uani 1 1 d . . .
C7 C 0.1898(2) 0.6083(14) 0.6434(5) 0.0310(11) Uani 1 1 d . . .
C6 C 0.1273(2) 0.5674(13) 0.5995(4) 0.0309(11) Uani 1 1 d . . .
C8 C 0.2389(3) 0.5184(14) 0.5815(4) 0.0321(12) Uani 1 1 d . . .
F3 F 0.35100(18) 0.0487(11) 0.5566(3) 0.0614(10) Uani 1 1 d . . .
F2 F 0.38664(17) 0.0679(12) 0.2853(3) 0.0609(10) Uani 1 1 d . . .
C4 C 0.1605(3) 0.3462(15) 0.4352(5) 0.0389(13) Uani 1 1 d . . .
C3 C 0.2243(2) 0.3894(12) 0.4768(4) 0.0267(11) Uani 1 1 d . . .
C5 C 0.1122(3) 0.4343(17) 0.4973(5) 0.0418(14) Uani 1 1 d . . .
C2 C 0.3448(2) 0.0959(13) 0.4587(4) 0.0265(10) Uani 1 1 d . . .
C1 C 0.3949(2) -0.0349(13) 0.3855(4) 0.0277(11) Uani 1 1 d . . .
F1 F 0.43827(19) -0.2174(10) 0.4262(3) 0.0576(10) Uani 1 1 d . . .
O1 O 0.4657(3) -0.1286(14) 0.1620(4) 0.0421(12) Uani 1 1 d . . .
H1A H 0.452(3) -0.150(16) 0.118(5) 0.016(19) Uiso 1 1 d . . .
H1B H 0.490(4) 0.01(3) 0.151(7) 0.08(3) Uiso 1 1 d . . .
H4 H 0.151(3) 0.263(11) 0.366(5) 0.021(13) Uiso 1 1 d . . .
H7 H 0.199(3) 0.705(14) 0.707(5) 0.033(16) Uiso 1 1 d . . .
H8 H 0.279(3) 0.540(14) 0.613(5) 0.033(14) Uiso 1 1 d . . .
H5 H 0.073(4) 0.41(2) 0.469(6) 0.06(2) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0380(4) 0.0483(4) 0.0532(4) -0.0068(3) 0.0159(3) 0.0032(3)
S1 0.0323(7) 0.0445(8) 0.0231(7) 0.0010(5) 0.0003(5) 0.0094(6)
C7 0.029(3) 0.040(3) 0.024(3) -0.003(2) 0.002(2) 0.000(2)
C6 0.028(3) 0.028(3) 0.038(3) 0.002(2) 0.011(2) 0.004(2)
C8 0.023(3) 0.035(3) 0.036(3) -0.002(2) -0.006(2) -0.002(2)
F3 0.057(2) 0.085(3) 0.042(2) 0.0065(19) 0.0053(17) 0.014(2)
F2 0.055(2) 0.087(3) 0.042(2) 0.008(2) 0.0085(17) 0.014(2)
C4 0.039(3) 0.046(3) 0.030(3) -0.008(3) -0.005(2) -0.001(3)
C3 0.026(3) 0.026(3) 0.027(2) 0.003(2) 0.003(2) 0.003(2)
C5 0.026(3) 0.053(4) 0.046(3) -0.004(3) -0.004(3) -0.002(3)
C2 0.027(3) 0.033(3) 0.018(2) 0.004(2) -0.0004(19) 0.000(2)
C1 0.022(2) 0.035(3) 0.025(2) 0.005(2) -0.004(2) 0.002(2)
F1 0.049(2) 0.076(3) 0.048(2) 0.0059(18) 0.0079(17) 0.0128(19)
O1 0.038(3) 0.061(3) 0.027(3) -0.008(2) 0.001(2) -0.010(2)

_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
Br1 C6 1.913(5) . ?
S1 C2 1.759(5) . ?
S1 C3 1.776(5) . ?
C7 C6 1.374(7) . ?
C7 C8 1.383(7) . ?
C6 C5 1.355(8) . ?
C8 C3 1.374(7) . ?
F3 C2 1.197(5) . ?
F2 C1 1.278(6) . ?
C4 C5 1.368(8) . ?
C4 C3 1.393(8) . ?
C2 C1 1.535(7) . ?
C1 F1 1.224(6) . ?

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 C3 105.3(2) . . ?
C6 C7 C8 119.7(5) . . ?
C5 C6 C7 121.6(5) . . ?
C5 C6 Br1 119.7(4) . . ?
C7 C6 Br1 118.7(4) . . ?
C3 C8 C7 119.4(5) . . ?
C5 C4 C3 120.5(5) . . ?
C8 C3 C4 119.7(5) . . ?
C8 C3 S1 124.9(4) . . ?
C4 C3 S1 115.1(4) . . ?
C6 C5 C4 119.2(5) . . ?
F3 C2 C1 120.8(4) . . ?
F3 C2 S1 127.0(4) . . ?
C1 C2 S1 112.2(3) . . ?
F1 C1 F2 126.4(5) . . ?
F1 C1 C2 119.3(4) . . ?
F2 C1 C2 114.3(4) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.117
