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_4132968
_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         'C51 H33 N O3 S2, C2 H4 Cl2'
_chemical_formula_sum            'C53 H37 Cl2 N O3 S2'
_chemical_formula_weight         870.85
_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             2015-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                110.535(3)
_cell_angle_beta                 97.936(3)
_cell_angle_gamma                94.658(3)
_cell_formula_units_Z            2
_cell_length_a                   11.3616(11)
_cell_length_b                   11.9741(11)
_cell_length_c                   16.8141(15)
_cell_measurement_reflns_used    9161
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.40
_cell_volume                     2100.8(3)
_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 0.997
_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  0.0351
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            114192
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        27.900
_diffrn_reflns_theta_max         27.933
_diffrn_reflns_theta_min         2.402
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0958 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.9525.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.307
_refine_diff_density_min         -1.423
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         10045
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0444
_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/[\s^2^(Fo^2^)+(0.0434P)^2^+2.4605P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8807
_reflns_number_total             10045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07617_si_001.cif
_cod_data_source_block           hjd96_0m
_cod_database_code               4132968
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.931
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) = Uanis(Cl2B)
Uanis(C62A) = Uanis(C62B)
Uanis(C61A) = Uanis(C61B)
Uanis(Cl1A) = Uanis(Cl1B)
3. Same fragment restrains
{Cl1A, Cl2A, C61A, C62A} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1B, Cl2B, C61B, C62B}
4. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(C61B)=Sof(H61C)=Sof(H61D)=Sof(C62B)=Sof(H62C)=
 Sof(H62D)=1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C61A)=Sof(H61A)=Sof(H61B)=Sof(C62A)=Sof(H62A)=
 Sof(H62B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C61A(H61A,H61B), C62A(H62A,H62B), C61B(H61C,H61D), C62B(H62C,H62D)
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), C41(H41),
 C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48), C49(H49), C50(H50),
  C51(H51)
;
_shelx_res_checksum              92149
_shelx_hkl_checksum              41939
_olex2_submission_special_instructions 'No special instructions were received'