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_4132974
_publ_section_title
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 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         'C43 H29 N O5, 1.81(C H Cl3)'
_chemical_formula_sum            'C44.81 H30.81 Cl5.44 N O5'
_chemical_formula_weight         856.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.962(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8387(8)
_cell_length_b                   24.1540(12)
_cell_length_c                   10.6840(5)
_cell_measurement_reflns_used    9180
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.863
_cell_measurement_theta_min      2.263
_cell_volume                     3983.2(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0504
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            212500
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        27.050
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.141
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.442
_exptl_absorpt_correction_T_max  0.3554
_exptl_absorpt_correction_T_min  0.3187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.8967.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1757
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0021(2)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         8785
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0360P)^2^+4.1795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                7865
_reflns_number_total             8785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07617_si_001.cif
_cod_data_source_block           lpc243
_cod_database_code               4132974
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.829
_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. Uiso/Uaniso restraints and constraints
Uiso(Cl4B) = Uiso(C52B) = Uiso(Cl6B) = Uiso(Cl5B) = Uiso(Cl3B) = Uiso(C51B) =
Uiso(Cl1B) = Uiso(Cl2B)
3. Same fragment restrains
{Cl1A, Cl2A, Cl3A, C51A} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1B, Cl2B, Cl3B, C51B}
{Cl4A, Cl5A, Cl6A, C52A} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl4B, Cl5B, Cl6B, C52B}
4. Others
 Sof(Cl4A)=Sof(Cl5A)=Sof(Cl6A)=Sof(C52A)=Sof(H52A)=FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C51A)=Sof(H51A)=FVAR(2)
 Sof(Cl4B)=Sof(Cl5B)=Sof(Cl6B)=Sof(C52B)=Sof(H52B)=FVAR(3)
 Sof(Cl1B)=Sof(Cl2B)=Sof(Cl3B)=Sof(C51B)=Sof(H51B)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C51A(H51A), C51B(H51B), C52A(H52A), C52B(H52B)
5.b 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), C38(H38), C39(H39), C40(H40)
5.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C43(H43A,H43B,H43C)
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_shelx_res_checksum              71919
_shelx_hkl_checksum              68526
_olex2_submission_special_instructions 'No special instructions were received'