# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

####################################################################### 
# 
# 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_zyf_150615
_database_code_depnum_ccdc_archive 'CCDC 1409264'
_audit_update_record             
;
2015-06-27 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;
_audit_creation_date             2015-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H8 Br F3 O2 S'
_chemical_formula_sum            'C16 H8 Br F3 O2 S'
_chemical_formula_weight         401.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.9202(2)
_cell_length_b                   7.94120(10)
_cell_length_c                   14.2105(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.2584(11)
_cell_angle_gamma                90.00
_cell_volume                     1457.67(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5049
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      71.6510
_cell_measurement_theta_min      3.0850
_exptl_absorpt_coefficient_mu    5.575
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5748
_diffrn_reflns_theta_full        71.65
_diffrn_reflns_theta_max         71.65
_diffrn_reflns_theta_min         4.68
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    8.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.2034   77.0000   60.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega   72.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega  113.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega   99.00  129.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   69.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   72.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
  7 omega   10.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.2034   77.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
  8 omega -124.00  -69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -95.0000   77.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
  9 omega -122.00  -55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -95.0000   77.0000   90.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1098704000
_diffrn_orient_matrix_UB_12      -0.0495336000
_diffrn_orient_matrix_UB_13      0.0297811000
_diffrn_orient_matrix_UB_21      0.0461074000
_diffrn_orient_matrix_UB_22      -0.1382148000
_diffrn_orient_matrix_UB_23      0.0645398000
_diffrn_orient_matrix_UB_31      0.0068527000
_diffrn_orient_matrix_UB_32      0.1267170000
_diffrn_orient_matrix_UB_33      0.0818240000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2623
_reflns_number_total             2725
_reflns_odcompleteness_completeness 98.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.182
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0773P)²+0.6099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1093
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.748267(19) 0.01605(4) 0.292355(17) 0.01933(15) Uani 1 d . . .
S2 S 1.31769(4) -0.33799(7) 0.54888(4) 0.01457(18) Uani 1 d . . .
F1 F 1.25577(12) -0.62013(19) 0.46755(11) 0.0241(3) Uani 1 d . . .
O2 O 1.01106(12) -0.2947(2) 0.50787(11) 0.0157(4) Uani 1 d . . .
F3 F 1.41130(13) -0.6172(2) 0.52765(11) 0.0288(4) Uani 1 d . . .
F4 F 1.37695(15) -0.4948(2) 0.39581(12) 0.0287(4) Uani 1 d . . .
O5 O 1.10648(14) -0.4405(2) 0.60858(11) 0.0182(4) Uani 1 d . . .
C6 C 0.8851(2) -0.0347(3) 0.33273(17) 0.0152(5) Uani 1 d . . .
C7 C 1.00059(18) -0.1858(3) 0.43357(15) 0.0131(5) Uani 1 d . . .
C8 C 1.28095(18) -0.0953(3) 0.37513(16) 0.0131(5) Uani 1 d . . .
C9 C 1.10597(18) -0.3446(3) 0.54337(15) 0.0134(5) Uani 1 d . . .
C10 C 1.18946(18) -0.1659(3) 0.42336(15) 0.0127(5) Uani 1 d . . .
C11 C 1.0673(2) -0.0006(3) 0.3172(2) 0.0159(6) Uani 1 d . . .
H11 H 1.1229 0.0495 0.2876 0.019 Uiso 1 calc . . R
C12 C 1.3403(2) -0.5249(3) 0.48113(19) 0.0169(5) Uani 1 d . . .
C13 C 1.4524(2) 0.0349(3) 0.28397(19) 0.0184(5) Uani 1 d . . .
H13 H 1.5099 0.0777 0.2537 0.022 Uiso 1 calc . . R
C14 C 1.29571(18) -0.1301(3) 0.27953(16) 0.0157(5) Uani 1 d . . .
H14 H 1.2482 -0.1964 0.2463 0.019 Uiso 1 calc . . R
C15 C 0.89996(18) -0.1485(3) 0.40540(16) 0.0153(5) Uani 1 d . . .
H15 H 0.8440 -0.1985 0.4345 0.018 Uiso 1 calc . . R
C16 C 1.19769(17) -0.2743(3) 0.49711(15) 0.0126(5) Uani 1 d . . .
C17 C 1.43766(19) 0.0707(3) 0.37785(18) 0.0191(5) Uani 1 d . . .
H17 H 1.4846 0.1390 0.4105 0.023 Uiso 1 calc . . R
C18 C 0.9677(2) 0.0415(3) 0.28815(17) 0.0172(5) Uani 1 d . . .
H18 H 0.9563 0.1190 0.2400 0.021 Uiso 1 calc . . R
C19 C 1.3525(2) 0.0048(3) 0.4238(2) 0.0158(5) Uani 1 d . . .
H19 H 1.3435 0.0278 0.4873 0.019 Uiso 1 calc . . R
C21 C 1.08681(17) -0.1167(3) 0.38978(15) 0.0121(4) Uani 1 d . . .
C22 C 1.38147(19) -0.0653(4) 0.23463(16) 0.0177(5) Uani 1 d . . .
H22 H 1.3915 -0.0889 0.1714 0.021 Uiso 1 calc . . R


_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 1.891(3) . ?
S2 C12 1.797(3) . ?
S2 C16 1.775(2) . ?
F1 C12 1.339(3) . ?
O2 C7 1.369(3) . ?
O2 C9 1.374(3) . ?
F3 C12 1.337(3) . ?
F4 C12 1.333(3) . ?
O5 C9 1.200(3) . ?
C6 C15 1.382(4) . ?
C6 C18 1.391(4) . ?
C7 C15 1.384(3) . ?
C7 C21 1.400(3) . ?
C8 C10 1.489(3) . ?
C8 C14 1.403(3) . ?
C8 C19 1.392(4) . ?
C9 C16 1.477(3) . ?
C10 C16 1.359(3) . ?
C10 C21 1.453(3) . ?
C11 H11 0.9300 . ?
C11 C18 1.383(4) . ?
C11 C21 1.402(3) . ?
C13 H13 0.9300 . ?
C13 C17 1.382(4) . ?
C13 C22 1.392(4) . ?
C14 H14 0.9300 . ?
C14 C22 1.390(3) . ?
C15 H15 0.9300 . ?
C17 H17 0.9300 . ?
C17 C19 1.394(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C22 H22 0.9300 . ?

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
C16 S2 C12 99.45(12) . . ?
C7 O2 C9 122.50(18) . . ?
C15 C6 Br1 118.64(19) . . ?
C15 C6 C18 122.0(2) . . ?
C18 C6 Br1 119.4(2) . . ?
O2 C7 C15 115.7(2) . . ?
O2 C7 C21 121.6(2) . . ?
C15 C7 C21 122.6(2) . . ?
C14 C8 C10 119.9(2) . . ?
C19 C8 C10 120.8(2) . . ?
C19 C8 C14 119.4(2) . . ?
O2 C9 C16 116.5(2) . . ?
O5 C9 O2 117.1(2) . . ?
O5 C9 C16 126.4(2) . . ?
C16 C10 C8 123.0(2) . . ?
C16 C10 C21 118.6(2) . . ?
C21 C10 C8 118.4(2) . . ?
C18 C11 H11 119.0 . . ?
C18 C11 C21 122.0(2) . . ?
C21 C11 H11 119.0 . . ?
F1 C12 S2 113.69(18) . . ?
F3 C12 S2 107.80(18) . . ?
F3 C12 F1 108.1(2) . . ?
F4 C12 S2 113.87(18) . . ?
F4 C12 F1 106.0(2) . . ?
F4 C12 F3 107.1(2) . . ?
C17 C13 H13 120.0 . . ?
C17 C13 C22 120.0(2) . . ?
C22 C13 H13 120.0 . . ?
C8 C14 H14 120.1 . . ?
C22 C14 C8 119.9(2) . . ?
C22 C14 H14 120.1 . . ?
C6 C15 C7 118.0(2) . . ?
C6 C15 H15 121.0 . . ?
C7 C15 H15 121.0 . . ?
C9 C16 S2 114.19(17) . . ?
C10 C16 S2 123.59(18) . . ?
C10 C16 C9 122.2(2) . . ?
C13 C17 H17 119.9 . . ?
C13 C17 C19 120.2(2) . . ?
C19 C17 H17 119.9 . . ?
C6 C18 H18 120.8 . . ?
C11 C18 C6 118.5(2) . . ?
C11 C18 H18 120.8 . . ?
C8 C19 C17 120.3(2) . . ?
C8 C19 H19 119.9 . . ?
C17 C19 H19 119.9 . . ?
C7 C21 C10 118.6(2) . . ?
C7 C21 C11 116.9(2) . . ?
C11 C21 C10 124.5(2) . . ?
C13 C22 H22 119.9 . . ?
C14 C22 C13 120.2(2) . . ?
C14 C22 H22 119.9 . . ?

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
Br1 C6 C15 C7 179.34(17) . . . . ?
Br1 C6 C18 C11 -178.37(19) . . . . ?
O2 C7 C15 C6 177.9(2) . . . . ?
O2 C7 C21 C10 1.4(3) . . . . ?
O2 C7 C21 C11 -177.2(2) . . . . ?
O2 C9 C16 S2 177.95(16) . . . . ?
O2 C9 C16 C10 0.1(3) . . . . ?
O5 C9 C16 S2 -2.1(3) . . . . ?
O5 C9 C16 C10 -180.0(2) . . . . ?
C7 O2 C9 O5 -180.0(2) . . . . ?
C7 O2 C9 C16 0.0(3) . . . . ?
C8 C10 C16 S2 3.0(3) . . . . ?
C8 C10 C16 C9 -179.3(2) . . . . ?
C8 C10 C21 C7 178.6(2) . . . . ?
C8 C10 C21 C11 -3.0(3) . . . . ?
C8 C14 C22 C13 -0.4(4) . . . . ?
C9 O2 C7 C15 179.5(2) . . . . ?
C9 O2 C7 C21 -0.8(3) . . . . ?
C10 C8 C14 C22 -179.5(2) . . . . ?
C10 C8 C19 C17 -179.7(2) . . . . ?
C12 S2 C16 C9 90.05(18) . . . . ?
C12 S2 C16 C10 -92.1(2) . . . . ?
C13 C17 C19 C8 -1.0(4) . . . . ?
C14 C8 C10 C16 118.0(3) . . . . ?
C14 C8 C10 C21 -61.9(3) . . . . ?
C14 C8 C19 C17 0.4(4) . . . . ?
C15 C6 C18 C11 0.9(4) . . . . ?
C15 C7 C21 C10 -178.9(2) . . . . ?
C15 C7 C21 C11 2.5(3) . . . . ?
C16 S2 C12 F1 -42.4(2) . . . . ?
C16 S2 C12 F3 -162.16(17) . . . . ?
C16 S2 C12 F4 79.1(2) . . . . ?
C16 C10 C21 C7 -1.3(3) . . . . ?
C16 C10 C21 C11 177.2(2) . . . . ?
C17 C13 C22 C14 -0.2(4) . . . . ?
C18 C6 C15 C7 0.0(4) . . . . ?
C18 C11 C21 C7 -1.4(4) . . . . ?
C18 C11 C21 C10 -179.9(2) . . . . ?
C19 C8 C10 C16 -61.9(3) . . . . ?
C19 C8 C10 C21 118.3(3) . . . . ?
C19 C8 C14 C22 0.3(4) . . . . ?
C21 C7 C15 C6 -1.8(4) . . . . ?
C21 C10 C16 S2 -177.09(17) . . . . ?
C21 C10 C16 C9 0.6(3) . . . . ?
C21 C11 C18 C6 -0.2(4) . . . . ?
C22 C13 C17 C19 0.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
