# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_glo8478
_database_code_depnum_ccdc_archive 'CCDC 1498887'
_audit_update_record             
;
2016-08-12 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 F S'
_chemical_formula_iupac          ?
_chemical_formula_weight         304.36

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.0149(4)
_cell_length_b                   13.4117(9)
_cell_length_c                   18.2153(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.601(2)
_cell_angle_gamma                90
_cell_volume                     1468.86(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.7041
_cell_measurement_theta_max      26.3238
_cell_measurement_temperature    138.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      138.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            29243
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_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.
;

_reflns_number_total             3020
_reflns_number_gt                2433
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0861
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_number_reflns         3020
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+1.0044P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.289
_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 0.0033 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'
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'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.9541(2) 0.60427(9) 0.53262(6) 0.0394(3) Uani d . . . 1 . .
S S1 0.30301(8) 0.44723(3) 0.66979(2) 0.02321(13) Uani d . . . 1 . .
C C1 0.5169(3) 0.53002(13) 0.65237(10) 0.0203(4) Uani d . . . 1 . .
C C2 0.6535(3) 0.53073(13) 0.59141(10) 0.0239(4) Uani d . . . 1 . .
H H2 0.6347 0.484 0.5525 0.029 Uiso calc U . R 1 . .
C C3 0.8160(3) 0.60241(14) 0.59083(10) 0.0266(4) Uani d . . . 1 . .
C C4 0.8492(3) 0.67285(14) 0.64583(11) 0.0269(4) Uani d . . . 1 . .
H H4 0.9638 0.7212 0.6425 0.032 Uiso calc U . R 1 . .
C C5 0.7129(3) 0.67134(13) 0.70540(10) 0.0228(4) Uani d . . . 1 . .
H H5 0.7317 0.7197 0.7432 0.027 Uiso calc U . R 1 . .
C C6 0.5461(3) 0.59850(13) 0.71042(9) 0.0193(4) Uani d . . . 1 . .
C C7 0.3939(3) 0.58159(12) 0.76903(9) 0.0187(4) Uani d . . . 1 . .
C C8 0.2544(3) 0.50339(13) 0.75507(9) 0.0200(4) Uani d . . . 1 . .
C C11 0.3949(3) 0.64581(12) 0.83560(9) 0.0180(4) Uani d . . . 1 . .
C C12 0.5823(3) 0.65044(13) 0.88237(10) 0.0230(4) Uani d . . . 1 . .
H H12 0.7101 0.6119 0.8719 0.028 Uiso calc U . R 1 . .
C C13 0.5829(3) 0.71115(14) 0.94410(10) 0.0270(4) Uani d . . . 1 . .
H H13 0.7109 0.7138 0.9758 0.032 Uiso calc U . R 1 . .
C C14 0.3979(3) 0.76792(13) 0.95972(10) 0.0263(4) Uani d . . . 1 . .
H H14 0.3989 0.8092 1.0021 0.032 Uiso calc U . R 1 . .
C C15 0.2109(3) 0.76443(14) 0.91337(10) 0.0259(4) Uani d . . . 1 . .
H H15 0.0838 0.8035 0.9238 0.031 Uiso calc U . R 1 . .
C C16 0.2102(3) 0.70372(14) 0.85177(10) 0.0232(4) Uani d . . . 1 . .
H H16 0.0821 0.7016 0.8201 0.028 Uiso calc U . R 1 . .
C C21 0.0812(3) 0.45888(12) 0.80091(10) 0.0199(4) Uani d . . . 1 . .
C C22 -0.1070(3) 0.41505(13) 0.76777(10) 0.0233(4) Uani d . . . 1 . .
H H22 -0.1217 0.4134 0.7157 0.028 Uiso calc U . R 1 . .
C C23 -0.2725(3) 0.37402(14) 0.80971(11) 0.0277(4) Uani d . . . 1 . .
H H23 -0.3995 0.3446 0.7863 0.033 Uiso calc U . R 1 . .
C C24 -0.2535(3) 0.37579(14) 0.88542(11) 0.0284(4) Uani d . . . 1 . .
H H24 -0.3688 0.3491 0.9141 0.034 Uiso calc U . R 1 . .
C C25 -0.0658(3) 0.41659(13) 0.91929(11) 0.0276(4) Uani d . . . 1 . .
H H25 -0.0514 0.4166 0.9714 0.033 Uiso calc U . R 1 . .
C C26 0.1018(3) 0.45754(13) 0.87779(10) 0.0239(4) Uani d . . . 1 . .
H H26 0.2307 0.4847 0.9016 0.029 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C3 . 1.365(2) ?
S1 C1 . 1.7352(18) ?
S1 C8 . 1.7583(18) ?
C1 C2 . 1.400(2) ?
C1 C6 . 1.408(2) ?
C2 C3 . 1.371(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.387(3) ?
C4 C5 . 1.378(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.405(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.444(2) ?
C7 C8 . 1.363(2) ?
C7 C11 . 1.487(2) ?
C8 C21 . 1.479(2) ?
C11 C16 . 1.394(2) ?
C11 C12 . 1.395(2) ?
C12 C13 . 1.388(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.385(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.388(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C22 . 1.398(2) ?
C21 C26 . 1.403(3) ?
C22 C23 . 1.386(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.381(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.384(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.390(3) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C8 . . 91.71(8) ?
C2 C1 C6 . . 121.83(16) ?
C2 C1 S1 . . 127.16(14) ?
C6 C1 S1 . . 110.97(13) ?
C3 C2 C1 . . 116.45(17) ?
C3 C2 H2 . . 121.8 ?
C1 C2 H2 . . 121.8 ?
F1 C3 C2 . . 117.91(17) ?
F1 C3 C4 . . 118.03(17) ?
C2 C3 C4 . . 124.06(17) ?
C5 C4 C3 . . 118.80(18) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 120.19(17) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C1 . . 118.64(16) ?
C5 C6 C7 . . 128.76(16) ?
C1 C6 C7 . . 112.61(15) ?
C8 C7 C6 . . 112.50(16) ?
C8 C7 C11 . . 125.90(16) ?
C6 C7 C11 . . 121.59(15) ?
C7 C8 C21 . . 130.16(16) ?
C7 C8 S1 . . 112.20(13) ?
C21 C8 S1 . . 117.59(13) ?
C16 C11 C12 . . 118.77(16) ?
C16 C11 C7 . . 120.66(15) ?
C12 C11 C7 . . 120.56(15) ?
C13 C12 C11 . . 120.29(17) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C14 C13 C12 . . 120.33(17) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 119.92(17) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C16 C15 C14 . . 119.74(18) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C11 . . 120.94(17) ?
C15 C16 H16 . . 119.5 ?
C11 C16 H16 . . 119.5 ?
C22 C21 C26 . . 118.27(17) ?
C22 C21 C8 . . 120.04(16) ?
C26 C21 C8 . . 121.68(16) ?
C23 C22 C21 . . 120.98(17) ?
C23 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
C24 C23 C22 . . 120.20(18) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 119.72(18) ?
C23 C24 H24 . . 120.1 ?
C25 C24 H24 . . 120.1 ?
C24 C25 C26 . . 120.58(18) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C25 C26 C21 . . 120.20(17) ?
C25 C26 H26 . . 119.9 ?
C21 C26 H26 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 S1 C1 C2 . . . . 177.31(16) ?
C8 S1 C1 C6 . . . . -0.51(13) ?
C6 C1 C2 C3 . . . . -0.7(3) ?
S1 C1 C2 C3 . . . . -178.31(14) ?
C1 C2 C3 F1 . . . . 179.13(15) ?
C1 C2 C3 C4 . . . . -0.6(3) ?
F1 C3 C4 C5 . . . . -179.28(16) ?
C2 C3 C4 C5 . . . . 0.5(3) ?
C3 C4 C5 C6 . . . . 1.0(3) ?
C4 C5 C6 C1 . . . . -2.2(3) ?
C4 C5 C6 C7 . . . . 177.14(17) ?
C2 C1 C6 C5 . . . . 2.1(2) ?
S1 C1 C6 C5 . . . . -179.93(13) ?
C2 C1 C6 C7 . . . . -177.37(16) ?
S1 C1 C6 C7 . . . . 0.59(18) ?
C5 C6 C7 C8 . . . . -179.77(17) ?
C1 C6 C7 C8 . . . . -0.4(2) ?
C5 C6 C7 C11 . . . . 1.0(3) ?
C1 C6 C7 C11 . . . . -179.59(15) ?
C6 C7 C8 C21 . . . . 177.46(16) ?
C11 C7 C8 C21 . . . . -3.4(3) ?
C6 C7 C8 S1 . . . . -0.03(19) ?
C11 C7 C8 S1 . . . . 179.15(13) ?
C1 S1 C8 C7 . . . . 0.32(14) ?
C1 S1 C8 C21 . . . . -177.52(13) ?
C8 C7 C11 C16 . . . . -62.6(2) ?
C6 C7 C11 C16 . . . . 116.54(19) ?
C8 C7 C11 C12 . . . . 118.5(2) ?
C6 C7 C11 C12 . . . . -62.4(2) ?
C16 C11 C12 C13 . . . . 0.5(3) ?
C7 C11 C12 C13 . . . . 179.47(16) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C13 C14 C15 . . . . -0.2(3) ?
C13 C14 C15 C16 . . . . 0.2(3) ?
C14 C15 C16 C11 . . . . 0.1(3) ?
C12 C11 C16 C15 . . . . -0.5(3) ?
C7 C11 C16 C15 . . . . -179.41(17) ?
C7 C8 C21 C22 . . . . 149.25(18) ?
S1 C8 C21 C22 . . . . -33.4(2) ?
C7 C8 C21 C26 . . . . -31.9(3) ?
S1 C8 C21 C26 . . . . 145.46(14) ?
C26 C21 C22 C23 . . . . 1.9(3) ?
C8 C21 C22 C23 . . . . -179.19(16) ?
C21 C22 C23 C24 . . . . -0.1(3) ?
C22 C23 C24 C25 . . . . -1.6(3) ?
C23 C24 C25 C26 . . . . 1.3(3) ?
C24 C25 C26 C21 . . . . 0.7(3) ?
C22 C21 C26 C25 . . . . -2.2(3) ?
C8 C21 C26 C25 . . . . 178.92(16) ?



#=============================================================================
#  end of cif data for "glo8478" (compound 3a)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

