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_4132969
_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         'C42 H27 N O3 S, C2 H6 O1 S1'
_chemical_formula_sum            'C44 H33 N O4 S2'
_chemical_formula_weight         703.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.184(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3098(10)
_cell_length_b                   18.9055(13)
_cell_length_c                   19.3753(15)
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.40
_cell_volume                     4077.5(6)
_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    'ShelXT (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  0.0565
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            122909
_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         2.227
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.6204
_exptl_absorpt_correction_T_min  0.5716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1643 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.9213.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0056(4)
_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   1.233
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         8328
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.233
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0267P)^2^+8.0968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                7681
_reflns_number_total             8328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07617_si_001.cif
_cod_data_source_block           hjd123_sq
_cod_database_code               4132969
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.902
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C51A, C51B}
{C52A, C52B}
3. Restrained distances
 C4A-C3 \\sim C4B-C3 \\sim C6-C5B \\sim C6-C5A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C41B) = Uanis(S1A)
Uanis(N1B) = Uanis(N1A)
Uanis(C51A) = Uanis(C51B)
Uanis(C52A) = Uanis(C52B)
Uanis(C4A) = Uanis(C4B) = Uanis(C5A) = Uanis(C5B)
Uanis(O2A) = Uanis(O2B)
Uanis(O3A) = Uanis(O3B)
5. Same fragment restrains
{O2A, O3A, C4A, C5A, N1A, C36A, C37A, C38A, C39A, C40A, C41A, C42A, S1A} sigma
for 1-2: 0.02, 1-3: 0.04
as
{O2B, O3B, C4B, C5B, N1B, C36B, C37B, C38B, C39B, C40B, C41B, C42B, S1B}
{S4A, O4A, C51A, C52A} sigma for 1-2: 0.02, 1-3: 0.04
as
{S4B, O4B, C51B, C52B}
6. Others
 Sof(O2B)=Sof(O3B)=Sof(C4B)=Sof(C5B)=Sof(N1B)=Sof(C36B)=Sof(C37B)=Sof(C38B)=
 Sof(H38B)=Sof(C39B)=Sof(H39B)=Sof(C40B)=Sof(H40B)=Sof(C41B)=Sof(H41B)=
 Sof(C42B)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(S1B)=1-FVAR(1)
 Sof(O2A)=Sof(O3A)=Sof(C4A)=Sof(C5A)=Sof(N1A)=Sof(C36A)=Sof(C37A)=Sof(C38A)=
 Sof(H38A)=Sof(C39A)=Sof(H39A)=Sof(C40A)=Sof(H40A)=Sof(C41A)=Sof(H41A)=
 Sof(C42A)=Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(S1A)=FVAR(1)
 Sof(S4B)=Sof(O4B)=Sof(C51B)=Sof(H51D)=Sof(H51E)=Sof(H51F)=Sof(C52B)=Sof(H52D)=
 Sof(H52E)=Sof(H52F)=1-FVAR(2)
 Sof(S4A)=Sof(O4A)=Sof(C51A)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C52A)=Sof(H52A)=
 Sof(H52B)=Sof(H52C)=FVAR(2)
7.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35), C38A(H38A), C39A(H39A), C40A(H40A), C41A(H41A),
 C38B(H38B), C39B(H39B), C40B(H40B), C41B(H41B)
7.b Idealised Me refined with riding coordinates:
 C51B(H51D,H51E,H51F), C52B(H52D,H52E,H52F)
7.c Idealised Me refined as rotating group:
 C42A(H42A,H42B,H42C), C42B(H42D,H42E,H42F), C51A(H51A,H51B,H51C), C52A(H52A,
 H52B,H52C)
;
_shelx_res_checksum              80584
_shelx_hkl_checksum              61733
_shelx_fab_checksum              16238
_olex2_submission_special_instructions 'No special instructions were received'