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_4132966
_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 O4, 0.45(C1 D1 Cl3)'
_chemical_formula_sum            'C46.44 H28 Cl1.34 D0.44 F3 N O4'
_chemical_formula_weight         769.44
_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
_audit_creation_date             2015-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                82.400(2)
_cell_angle_beta                 79.506(3)
_cell_angle_gamma                81.035(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7573(7)
_cell_length_b                   11.8897(8)
_cell_length_c                   16.0751(11)
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.543
_cell_measurement_theta_min      2.592
_cell_volume                     1800.9(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0383
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            75318
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.560
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.281
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.6942
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1600 before and 0.0521 after correction.
The Ratio of minimum to maximum transmission is 0.9334.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0122(11)
_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   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         8316
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0527P)^2^+1.4292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1260
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7258
_reflns_number_total             8316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07617_si_001.cif
_cod_data_source_block           hjc203
_cod_database_code               4132966
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1S-Cl1 = C1S-Cl2 = C1S-Cl3
 1.76 with sigma of 0.02
 Cl1-Cl2 = Cl2-Cl3 = Cl3-Cl1
 2.9 with sigma of 0.02
 C2S-Cl4 = C2S-Cl5 = C2S-Cl6
 1.76 with sigma of 0.02
 Cl4-Cl5 = Cl5-Cl6 = Cl6-Cl4
 2.9 with sigma of 0.02
 C3S-Cl7 = C3S-Cl8 = C3S-Cl9
 1.76 with sigma of 0.02
 Cl7-Cl8 = Cl8-Cl9 = Cl9-Cl7
 2.9 with sigma of 0.02
 C4S-Cl10 = C4S-Cl11 = C4S-Cl12
 1.76 with sigma of 0.02
 Cl10-Cl11 = Cl11-Cl12 = Cl12-Cl10
 2.9 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1S) = Uanis(C2S) = Uanis(C3S) = Uanis(C4S)
Uanis(Cl1) = Uanis(Cl4) = Uanis(Cl8)
Uanis(Cl3) = Uanis(Cl6) = Uanis(Cl7)
Uanis(Cl2) = Uanis(Cl5) = Uanis(Cl9)
Uanis(Cl1) = Uanis(Cl4) = Uanis(Cl8) = Uanis(Cl11)
Uanis(Cl2) = Uanis(Cl5) = Uanis(Cl9) = Uanis(Cl10)
Uanis(Cl3) = Uanis(Cl6) = Uanis(Cl7) = Uanis(Cl12)
4. Rigid body (RIGU) restrains
 C1S, Cl1, Cl2, Cl3, C2S, Cl4, Cl5, Cl6, C3S, Cl7, Cl8, Cl9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1S)=Sof(D1S)=Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=FVAR(1)
 Sof(C2S)=Sof(D2S)=Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=FVAR(2)
 Sof(C3S)=Sof(D3S)=Sof(Cl7)=Sof(Cl8)=Sof(Cl9)=FVAR(3)
 Sof(C4S)=Sof(D4S)=Sof(Cl10)=Sof(Cl11)=Sof(Cl12)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C1S(D1S), C2S(D2S), C3S(D3S), C4S(D4S)
6.b 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)
;
_shelx_res_checksum              3717
_shelx_hkl_checksum              51634
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'