# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_esser_mh_192_0m
_database_code_depnum_ccdc_archive 'CCDC 1532986'
_audit_update_record             
;
2017-02-15 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;
_audit_creation_date             2017-02-15
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H18 S2'
_chemical_formula_sum            'C28 H18 S2'
_chemical_formula_weight         418.54
_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 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.307(3)
_cell_length_b                   5.5294(14)
_cell_length_c                   15.071(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.214(10)
_cell_angle_gamma                90
_cell_volume                     1002.4(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5549
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1156 before and 0.0349 after correction. The Ratio of minimum to maximum transmission is 0.9453. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8126
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.108
_diffrn_reflns_theta_min         1.946
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2027
_reflns_number_total             2191
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+1.0946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0880
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S1 S 0.37624(3) 0.04746(7) 0.59229(3) 0.01557(12) Uani 1 1 d . . . . .
C1 C 0.40997(14) 0.1487(3) 0.89737(11) 0.0208(4) Uani 1 1 d . . . . .
H1 H 0.414829 0.167800 0.960732 0.025 Uiso 1 1 calc R . . . .
C2 C 0.35920(13) -0.0546(3) 0.85277(11) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.328840 -0.174266 0.885707 0.022 Uiso 1 1 calc R . . . .
C3 C 0.35255(13) -0.0839(3) 0.76000(11) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.318685 -0.224329 0.729874 0.020 Uiso 1 1 calc R . . . .
C4 C 0.39584(12) 0.0938(3) 0.71142(10) 0.0141(3) Uani 1 1 d . . . . .
C5 C 0.47163(13) 0.2531(3) 0.56354(10) 0.0147(3) Uani 1 1 d . . . . .
C6 C 0.44874(13) 0.4373(3) 0.50335(10) 0.0154(3) Uani 1 1 d . . . . .
C7 C 0.44569(13) 0.2991(3) 0.75572(11) 0.0169(3) Uani 1 1 d . . . . .
H7 H 0.474121 0.421473 0.722669 0.020 Uiso 1 1 calc R . . . .
C8 C 0.45359(13) 0.3237(3) 0.84884(11) 0.0196(3) Uani 1 1 d . . . . .
H8 H 0.489209 0.461841 0.879453 0.024 Uiso 1 1 calc R . . . .
C9 C 0.59442(13) 0.2455(3) 0.59700(10) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.65936(13) 0.0814(3) 0.65311(10) 0.0174(3) Uani 1 1 d . . . . .
H10 H 0.626792 -0.051348 0.677899 0.021 Uiso 1 1 calc R . . . .
C11 C 0.77494(13) 0.1152(3) 0.67279(10) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.821089 0.003127 0.711225 0.022 Uiso 1 1 calc R . . . .
C12 C 0.17690(13) 0.6909(3) 0.36283(10) 0.0182(3) Uani 1 1 d . . . . .
H12 H 0.098529 0.670068 0.347506 0.022 Uiso 1 1 calc R . . . .
C13 C 0.24248(13) 0.5254(3) 0.42113(10) 0.0172(3) Uani 1 1 d . . . . .
H13 H 0.209679 0.392535 0.445680 0.021 Uiso 1 1 calc R . . . .
C14 C 0.35690(13) 0.5607(3) 0.44210(10) 0.0156(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
S1 C4 1.7787(17) . ?
S1 C5 1.7534(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(2) . ?
C1 C8 1.388(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(2) . ?
C4 C7 1.392(2) . ?
C5 C6 1.353(2) . ?
C5 C9 1.489(2) . ?
C6 C6 1.462(3) 3_666 ?
C6 C14 1.468(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(2) . ?
C9 C14 1.415(2) 3_666 ?
C10 H10 0.9500 . ?
C10 C11 1.403(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(2) 3_666 ?
C12 H12 0.9500 . ?
C12 C13 1.400(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(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
C5 S1 C4 101.60(7) . . ?
C2 C1 H1 120.2 . . ?
C8 C1 H1 120.2 . . ?
C8 C1 C2 119.61(15) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.35(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.76(15) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 S1 116.26(12) . . ?
C7 C4 S1 123.61(12) . . ?
C7 C4 C3 120.04(14) . . ?
C6 C5 S1 126.76(12) . . ?
C6 C5 C9 107.49(14) . . ?
C9 C5 S1 125.64(12) . . ?
C5 C6 C6 110.07(17) . 3_666 ?
C5 C6 C14 142.65(15) . . ?
C6 C6 C14 107.28(17) 3_666 . ?
C4 C7 H7 120.2 . . ?
C4 C7 C8 119.54(15) . . ?
C8 C7 H7 120.2 . . ?
C1 C8 C7 120.68(15) . . ?
C1 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C5 130.01(15) . . ?
C10 C9 C14 120.89(15) . 3_666 ?
C14 C9 C5 109.04(14) 3_666 . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.27(16) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.20(15) 3_666 . ?
C12 C11 H11 119.4 3_666 . ?
C11 C12 H12 119.6 3_666 . ?
C11 C12 C13 120.75(15) 3_666 . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.19(15) . . ?
C14 C13 H13 120.9 . . ?
C9 C14 C6 106.05(14) 3_666 . ?
C13 C14 C6 133.31(15) . . ?
C13 C14 C9 120.61(14) . 3_666 ?

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
S1 C4 C7 C8 177.52(12) . . . . ?
S1 C5 C6 C6 -178.41(13) . . . 3_666 ?
S1 C5 C6 C14 2.6(3) . . . . ?
S1 C5 C9 C10 2.0(2) . . . . ?
S1 C5 C9 C14 179.25(11) . . . 3_666 ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C2 C1 C8 C7 0.8(2) . . . . ?
C2 C3 C4 S1 -176.57(12) . . . . ?
C2 C3 C4 C7 0.2(2) . . . . ?
C3 C4 C7 C8 1.0(2) . . . . ?
C4 S1 C5 C6 -121.70(15) . . . . ?
C4 S1 C5 C9 62.62(14) . . . . ?
C4 C7 C8 C1 -1.5(2) . . . . ?
C5 S1 C4 C3 -164.49(12) . . . . ?
C5 S1 C4 C7 18.89(15) . . . . ?
C5 C6 C14 C9 177.9(2) . . . 3_666 ?
C5 C6 C14 C13 0.0(3) . . . . ?
C5 C9 C10 C11 178.84(15) . . . . ?
C6 C5 C9 C10 -174.37(16) . . . . ?
C6 C5 C9 C14 2.88(17) . . . 3_666 ?
C6 C6 C14 C9 -1.18(19) 3_666 . . 3_666 ?
C6 C6 C14 C13 -179.06(17) 3_666 . . . ?
C8 C1 C2 C3 0.4(2) . . . . ?
C9 C5 C6 C6 -2.1(2) . . . 3_666 ?
C9 C5 C6 C14 178.89(19) . . . . ?
C9 C10 C11 C12 0.3(2) . . . 3_666 ?
C11 C12 C13 C14 -0.1(2) 3_666 . . . ?
C12 C13 C14 C6 175.60(16) . . . . ?
C12 C13 C14 C9 -2.0(2) . . . 3_666 ?
C14 C9 C10 C11 1.9(2) 3_666 . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id MH_192
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_esser_mh_209_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1582024'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H16 F6 S2'
_chemical_formula_sum            'C30 H16 F6 S2'
_chemical_formula_weight         554.55
_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 0.0033 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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.951(5)
_cell_length_b                   9.552(5)
_cell_length_c                   14.344(9)
_cell_angle_alpha                103.52(2)
_cell_angle_beta                 91.36(2)
_cell_angle_gamma                101.337(15)
_cell_volume                     1166.0(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.436
_cell_measurement_theta_min      2.664
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1341 before and 0.0376 after correction. The Ratio of minimum to maximum transmission is 0.9353. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17667
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.464
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4034
_reflns_number_total             4758
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4758
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.7549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0948
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C23-F1A \\sim C23-F2A \\sim C23-F3A \\sim C23-F4A \\sim C23-F5A \\sim C23-F6A
 with sigma of 0.02
 F1A-F2A \\sim F2A-F3A \\sim F3A-F1A \\sim F4A-F5A \\sim F5A-F6A \\sim F6A-F4A
 with sigma of 0.04
 C20-F1A \\sim C20-F2A \\sim C20-F3A \\sim C20-F4A \\sim C20-F5A \\sim C20-F6A
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
C20 \\sim C23 \\sim F1A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim F6A:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C20, C23, F1A, F2A, F3A, F4A, F5A, F6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C26(H26), C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S1 S 0.78265(5) 0.09169(5) 0.37530(3) 0.01902(12) Uani 1 1 d . . . . .
C1 C 0.61270(19) 0.1406(2) 0.41814(11) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.45503(19) 0.0524(2) 0.38616(11) 0.0182(4) Uani 1 1 d . . . . .
S2 S 0.25649(5) 0.40852(5) 0.62619(3) 0.01876(12) Uani 1 1 d . . . . .
C3 C 0.4052(2) -0.0749(2) 0.31483(12) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.475296 -0.117929 0.274696 0.025 Uiso 1 1 calc R . . . .
F4 F 0.34946(12) 0.33502(13) 1.07847(7) 0.0286(3) Uani 1 1 d . . . . .
C4 C 0.2486(2) -0.1393(2) 0.30290(12) 0.0228(4) Uani 1 1 d . . . . .
H4 H 0.212785 -0.227548 0.254690 0.027 Uiso 1 1 calc R . . . .
F5 F 0.10441(12) 0.31470(13) 1.06430(7) 0.0288(3) Uani 1 1 d . . . . .
C5 C 0.1451(2) -0.0756(2) 0.36074(12) 0.0216(4) Uani 1 1 d . . . . .
H5 H 0.039698 -0.121265 0.351808 0.026 Uiso 1 1 calc R . . . .
C6 C 0.19469(19) 0.0555(2) 0.43217(11) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.123819 0.100029 0.470788 0.023 Uiso 1 1 calc R . . . .
F6 F 0.25214(12) 0.52970(12) 1.10288(7) 0.0276(3) Uani 1 1 d . . . . .
C7 C 0.34987(19) 0.11860(19) 0.44503(11) 0.0168(3) Uani 1 1 d . . . . .
C8 C 0.44150(19) 0.24882(19) 0.51313(11) 0.0166(3) Uani 1 1 d . . . . .
C9 C 0.43041(19) 0.36469(19) 0.58629(11) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.58753(18) 0.45603(19) 0.61652(11) 0.0167(3) Uani 1 1 d . . . . .
C11 C 0.6377(2) 0.5876(2) 0.68440(12) 0.0197(4) Uani 1 1 d . . . . .
H11 H 0.567447 0.634396 0.722140 0.024 Uiso 1 1 calc R . . . .
C12 C 0.7943(2) 0.6503(2) 0.69634(12) 0.0211(4) Uani 1 1 d . . . . .
H12 H 0.830214 0.740987 0.742320 0.025 Uiso 1 1 calc R . . . .
C13 C 0.8981(2) 0.5815(2) 0.64172(12) 0.0204(4) Uani 1 1 d . . . . .
H13 H 1.003866 0.625573 0.651199 0.024 Uiso 1 1 calc R . . . .
C14 C 0.84845(19) 0.4482(2) 0.57311(11) 0.0190(4) Uani 1 1 d . . . . .
H14 H 0.919533 0.401095 0.536388 0.023 Uiso 1 1 calc R . . . .
C15 C 0.69314(19) 0.38615(19) 0.55972(11) 0.0167(3) Uani 1 1 d . . . . .
C16 C 0.60209(18) 0.25518(19) 0.49278(11) 0.0172(3) Uani 1 1 d . . . . .
C17 C 0.76318(18) 0.09454(19) 0.25183(11) 0.0167(3) Uani 1 1 d . . . . .
C18 C 0.8376(2) 0.0043(2) 0.18613(12) 0.0216(4) Uani 1 1 d . . . . .
H18 H 0.894228 -0.058301 0.207245 0.026 Uiso 1 1 calc R . . . .
C19 C 0.8282(2) 0.0065(2) 0.08969(12) 0.0223(4) Uani 1 1 d . . . . .
H19 H 0.879802 -0.053692 0.044931 0.027 Uiso 1 1 calc R . . . .
C20 C 0.74344(19) 0.09659(19) 0.05827(12) 0.0183(3) Uani 1 1 d D U . . .
C21 C 0.6715(2) 0.1883(2) 0.12395(13) 0.0232(4) Uani 1 1 d . . . . .
H21 H 0.615261 0.251081 0.102733 0.028 Uiso 1 1 calc R . . . .
C22 C 0.6821(2) 0.1879(2) 0.22060(12) 0.0229(4) Uani 1 1 d . . . . .
H22 H 0.634046 0.251340 0.265626 0.028 Uiso 1 1 calc R . . . .
C23 C 0.7324(2) 0.0954(2) -0.04646(12) 0.0222(4) Uani 1 1 d D U . . .
F1A F 0.8389(15) 0.0380(17) -0.0917(7) 0.057(4) Uani 0.131(4) 1 d D U P A 1
F2A F 0.7640(19) 0.2383(10) -0.0529(7) 0.056(4) Uani 0.131(4) 1 d D U P A 1
F3A F 0.6018(11) 0.035(2) -0.0823(8) 0.065(5) Uani 0.131(4) 1 d D U P A 1
F4A F 0.60984(19) 0.1429(2) -0.07284(10) 0.0383(5) Uani 0.869(4) 1 d D U P A 2
F5A F 0.7204(2) -0.04002(16) -0.10463(9) 0.0417(6) Uani 0.869(4) 1 d D U P A 2
F6A F 0.85347(18) 0.1788(2) -0.07257(10) 0.0448(6) Uani 0.869(4) 1 d D U P A 2
C24 C 0.26159(18) 0.40036(19) 0.74866(11) 0.0159(3) Uani 1 1 d . . . . .
C25 C 0.13116(19) 0.4251(2) 0.79672(12) 0.0194(4) Uani 1 1 d . . . . .
H25 H 0.047543 0.444988 0.763650 0.023 Uiso 1 1 calc R . . . .
C26 C 0.12400(19) 0.4206(2) 0.89221(12) 0.0205(4) Uani 1 1 d . . . . .
H26 H 0.035128 0.436763 0.924421 0.025 Uiso 1 1 calc R . . . .
C27 C 0.24681(19) 0.39234(19) 0.94147(11) 0.0174(3) Uani 1 1 d . . . . .
C28 C 0.37595(19) 0.3673(2) 0.89404(12) 0.0197(4) Uani 1 1 d . . . . .
H28 H 0.459294 0.347467 0.927384 0.024 Uiso 1 1 calc R . . . .
C29 C 0.38397(19) 0.3712(2) 0.79797(12) 0.0189(4) Uani 1 1 d . . . . .
H29 H 0.472660 0.354115 0.765843 0.023 Uiso 1 1 calc R . . . .
C30 C 0.23870(19) 0.3921(2) 1.04601(12) 0.0213(4) 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
S1 C1 1.7606(18) . ?
S1 C17 1.782(2) . ?
C1 C2 1.494(2) . ?
C1 C16 1.360(2) . ?
C2 C3 1.381(2) . ?
C2 C7 1.421(2) . ?
S2 C9 1.7643(18) . ?
S2 C24 1.7765(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
F4 C30 1.344(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(3) . ?
F5 C30 1.348(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.406(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(2) . ?
F6 C30 1.356(2) . ?
C7 C8 1.472(2) . ?
C8 C9 1.357(2) . ?
C8 C16 1.466(2) . ?
C9 C10 1.496(2) . ?
C10 C11 1.383(2) . ?
C10 C15 1.426(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.401(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.399(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(2) . ?
C15 C16 1.467(2) . ?
C17 C18 1.397(2) . ?
C17 C22 1.396(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(3) . ?
C20 C21 1.391(2) . ?
C20 C23 1.500(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9500 . ?
C23 F1A 1.303(8) . ?
C23 F2A 1.365(9) . ?
C23 F3A 1.237(9) . ?
C23 F4A 1.345(2) . ?
C23 F5A 1.348(2) . ?
C23 F6A 1.330(2) . ?
C24 C25 1.402(2) . ?
C24 C29 1.397(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.396(2) . ?
C27 C28 1.388(2) . ?
C27 C30 1.503(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.390(2) . ?
C29 H29 0.9500 . ?

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 S1 C17 102.10(8) . . ?
C2 C1 S1 125.40(13) . . ?
C16 C1 S1 126.24(13) . . ?
C16 C1 C2 108.00(14) . . ?
C3 C2 C1 130.53(16) . . ?
C3 C2 C7 120.77(16) . . ?
C7 C2 C1 108.68(15) . . ?
C9 S2 C24 104.35(8) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.58(16) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.94(17) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.75(17) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.48(16) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C8 106.17(15) . . ?
C6 C7 C2 120.46(16) . . ?
C6 C7 C8 133.35(15) . . ?
C9 C8 C7 142.76(16) . . ?
C9 C8 C16 109.66(15) . . ?
C16 C8 C7 107.57(14) . . ?
C8 C9 S2 124.46(13) . . ?
C8 C9 C10 108.14(14) . . ?
C10 C9 S2 126.95(13) . . ?
C11 C10 C9 131.17(15) . . ?
C11 C10 C15 120.59(16) . . ?
C15 C10 C9 108.23(15) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.65(16) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.94(17) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.81(16) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.71(16) . . ?
C15 C14 H14 120.6 . . ?
C10 C15 C16 106.40(15) . . ?
C14 C15 C10 120.29(16) . . ?
C14 C15 C16 133.28(15) . . ?
C1 C16 C8 109.58(15) . . ?
C1 C16 C15 142.85(16) . . ?
C8 C16 C15 107.55(14) . . ?
C18 C17 S1 118.02(13) . . ?
C22 C17 S1 122.00(13) . . ?
C22 C17 C18 119.93(16) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.58(16) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.36(16) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C23 119.53(15) . . ?
C21 C20 C19 120.04(16) . . ?
C21 C20 C23 120.43(16) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.84(17) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.22(16) . . ?
C21 C22 H22 119.9 . . ?
F1A C23 C20 111.5(5) . . ?
F1A C23 F2A 104.4(9) . . ?
F2A C23 C20 107.4(4) . . ?
F3A C23 C20 110.0(5) . . ?
F3A C23 F1A 113.6(9) . . ?
F3A C23 F2A 109.7(9) . . ?
F4A C23 C20 113.25(15) . . ?
F4A C23 F5A 105.08(16) . . ?
F5A C23 C20 113.04(16) . . ?
F6A C23 C20 113.02(15) . . ?
F6A C23 F4A 106.23(18) . . ?
F6A C23 F5A 105.51(17) . . ?
C25 C24 S2 115.77(13) . . ?
C29 C24 S2 124.73(13) . . ?
C29 C24 C25 119.50(15) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.10(15) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.28(15) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C30 119.51(15) . . ?
C28 C27 C26 119.78(15) . . ?
C28 C27 C30 120.71(15) . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.33(16) . . ?
C29 C28 H28 119.8 . . ?
C24 C29 H29 120.0 . . ?
C28 C29 C24 120.01(15) . . ?
C28 C29 H29 120.0 . . ?
F4 C30 F5 107.00(15) . . ?
F4 C30 F6 106.59(14) . . ?
F4 C30 C27 112.61(14) . . ?
F5 C30 F6 105.60(14) . . ?
F5 C30 C27 112.45(14) . . ?
F6 C30 C27 112.11(15) . . ?

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
S1 C1 C2 C3 -5.3(3) . . . . ?
S1 C1 C2 C7 173.10(12) . . . . ?
S1 C1 C16 C8 -173.42(13) . . . . ?
S1 C1 C16 C15 8.6(3) . . . . ?
S1 C17 C18 C19 -178.33(14) . . . . ?
S1 C17 C22 C21 179.05(14) . . . . ?
C1 S1 C17 C18 -152.86(14) . . . . ?
C1 S1 C17 C22 29.87(17) . . . . ?
C1 C2 C3 C4 176.98(17) . . . . ?
C1 C2 C7 C6 -178.14(15) . . . . ?
C1 C2 C7 C8 0.54(18) . . . . ?
C2 C1 C16 C8 -0.12(19) . . . . ?
C2 C1 C16 C15 -178.1(2) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C2 C7 C8 C9 178.2(2) . . . . ?
C2 C7 C8 C16 -0.61(18) . . . . ?
S2 C9 C10 C11 4.4(3) . . . . ?
S2 C9 C10 C15 -174.31(12) . . . . ?
S2 C24 C25 C26 179.80(14) . . . . ?
S2 C24 C29 C28 -179.97(14) . . . . ?
C3 C2 C7 C6 0.4(2) . . . . ?
C3 C2 C7 C8 179.11(15) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C5 C6 C7 C8 -177.44(17) . . . . ?
C6 C7 C8 C9 -3.4(4) . . . . ?
C6 C7 C8 C16 177.83(18) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
C7 C8 C9 S2 -4.9(3) . . . . ?
C7 C8 C9 C10 -177.7(2) . . . . ?
C7 C8 C16 C1 0.46(19) . . . . ?
C7 C8 C16 C15 179.19(13) . . . . ?
C8 C9 C10 C11 176.94(17) . . . . ?
C8 C9 C10 C15 -1.81(18) . . . . ?
C9 S2 C24 C25 -177.33(14) . . . . ?
C9 S2 C24 C29 2.48(18) . . . . ?
C9 C8 C16 C1 -178.77(14) . . . . ?
C9 C8 C16 C15 -0.04(19) . . . . ?
C9 C10 C11 C12 -178.83(16) . . . . ?
C9 C10 C15 C14 -179.95(15) . . . . ?
C9 C10 C15 C16 1.73(17) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C10 C15 C16 C1 176.9(2) . . . . ?
C10 C15 C16 C8 -1.08(18) . . . . ?
C11 C10 C15 C14 1.1(2) . . . . ?
C11 C10 C15 C16 -177.18(15) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C10 -1.3(2) . . . . ?
C13 C14 C15 C16 176.49(17) . . . . ?
C14 C15 C16 C1 -1.1(4) . . . . ?
C14 C15 C16 C8 -179.09(18) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C16 C1 C2 C3 -178.66(17) . . . . ?
C16 C1 C2 C7 -0.27(19) . . . . ?
C16 C8 C9 S2 173.83(12) . . . . ?
C16 C8 C9 C10 1.11(19) . . . . ?
C17 S1 C1 C2 64.00(16) . . . . ?
C17 S1 C1 C16 -123.82(16) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C17 C22 C21 1.8(3) . . . . ?
C18 C19 C20 C21 2.0(3) . . . . ?
C18 C19 C20 C23 -178.89(16) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C19 C20 C23 F1A -17.5(8) . . . . ?
C19 C20 C23 F2A -131.3(8) . . . . ?
C19 C20 C23 F3A 109.4(10) . . . . ?
C19 C20 C23 F4A 157.85(18) . . . . ?
C19 C20 C23 F5A 38.5(2) . . . . ?
C19 C20 C23 F6A -81.3(2) . . . . ?
C20 C21 C22 C17 -0.7(3) . . . . ?
C21 C20 C23 F1A 161.6(8) . . . . ?
C21 C20 C23 F2A 47.8(8) . . . . ?
C21 C20 C23 F3A -71.5(10) . . . . ?
C21 C20 C23 F4A -23.0(3) . . . . ?
C21 C20 C23 F5A -142.38(19) . . . . ?
C21 C20 C23 F6A 97.8(2) . . . . ?
C22 C17 C18 C19 -1.0(3) . . . . ?
C23 C20 C21 C22 179.72(17) . . . . ?
C24 S2 C9 C8 120.27(15) . . . . ?
C24 S2 C9 C10 -68.38(16) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C25 C24 C29 C28 -0.2(3) . . . . ?
C25 C26 C27 C28 -0.6(3) . . . . ?
C25 C26 C27 C30 178.27(17) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
C26 C27 C30 F4 167.47(16) . . . . ?
C26 C27 C30 F5 46.5(2) . . . . ?
C26 C27 C30 F6 -72.3(2) . . . . ?
C27 C28 C29 C24 0.0(3) . . . . ?
C28 C27 C30 F4 -13.7(2) . . . . ?
C28 C27 C30 F5 -134.64(17) . . . . ?
C28 C27 C30 F6 106.54(19) . . . . ?
C29 C24 C25 C26 0.0(3) . . . . ?
C30 C27 C28 C29 -178.45(17) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
