Tipping the Balance between S-π and O-π Interactions.
Hwang, Jungwun; Li, Ping; Smith, Mark D.; Warden, Constance E.; Sirianni, Dominic A.; Vik, Erik C.; Maier, Josef M.; Yehl, Christopher J.; Sherrill, C. David; Shimizu, Ken D.; Journal of the American Chemical Society 140 (2018) 13301–13307; doi:10.1021/jacs.8b07617

data_4132967
_publ_section_title
;
 Tipping the Balance between S-\p and O-\p Interactions.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13301
_journal_page_last               13307
_journal_paper_doi               10.1021/jacs.8b07617
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C46 H28 F3 N O3 S, 0.5(C6 D5 Br)'
_chemical_formula_sum            'C49 H28 Br0.5 D2.5 F3 N O3 S'
_chemical_formula_weight         812.77
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                85.793(2)
_cell_angle_beta                 82.542(2)
_cell_angle_gamma                81.689(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0150(5)
_cell_length_b                   11.8686(5)
_cell_length_c                   16.0169(8)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.30
_cell_volume                     1865.01(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEXII v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            82868
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.370
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.217
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  0.6468
_exptl_absorpt_correction_T_min  0.5991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1149 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.9263.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       wedge
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7614
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0453
_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/[\s^2^(Fo^2^)+(0.0392P)^2^+1.8783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6057
_reflns_number_total             7614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07617_si_001.cif
_cod_data_source_block           hjd87
_cod_original_formula_sum        'C49 H28 Br0.50 D2.50 F3 N O3 S'
_cod_database_code               4132967
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.753
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Br1S-C1S \\sim Br2S-C7S
 with sigma of 0.01
 Br1S-C2S \\sim Br1S-C6S \\sim Br2S-C8S \\sim Br2S-C12S
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uiso(C1S) = Uiso(C2S) = Uiso(C3S) = Uiso(C4S) = Uiso(C5S) = Uiso(C6S) =
Uiso(C7S) = Uiso(C8S) = Uiso(C9S) = Uiso(C10S) = Uiso(C11S) = Uiso(C12S)
4. Others
 Sof(Br2S)=Sof(C7S)=Sof(C8S)=Sof(D8S)=Sof(C9S)=Sof(D9S)=Sof(C10S)=Sof(D10S)=
 Sof(C11S)=Sof(D11S)=Sof(C12S)=Sof(D12S)=0.5*(1-FVAR(2))
 Sof(Br1S)=Sof(C1S)=Sof(C2S)=Sof(D2S)=Sof(C3S)=Sof(D3S)=Sof(C4S)=Sof(D4S)=
 Sof(C5S)=Sof(D5S)=Sof(C6S)=Sof(D6S)=0.5*FVAR(2)
5.a :
 C1S(C2S,C3S,C4S,C5S,C6S,Br2S), C7S(C8S,C9S,C10S,C11S,C12S)
5.b Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
5.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C36(H36), C37(H37), C38(H38), C39(H39),
 C41(H41), C42(H42), C44(H44), C45(H45), C2S(D2S), C3S(D3S), C4S(D4S), C5S(D5S),
  C6S(D6S), C8S(D8S), C9S(D9S), C10S(D10S), C11S(D11S), C12S(D12S)
;
_shelx_res_checksum              86419
_shelx_hkl_checksum              94673
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'