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_4132972
_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         'C33 H23 N O3'
_chemical_formula_sum            'C33 H23 N O3'
_chemical_formula_weight         481.52
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_Hall           '-P 3'
_space_group_name_H-M_alt        'P -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   36.213(2)
_cell_length_b                   36.213(2)
_cell_length_c                   9.4339(6)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.25
_cell_volume                     10714.0(11)
_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    'XS (Sheldrick, 2008)'
_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  0.1082
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            150893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.030
_diffrn_reflns_theta_max         25.030
_diffrn_reflns_theta_min         2.159
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.6936
_exptl_absorpt_correction_T_min  0.6430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1031 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.9270.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       blade
_exptl_crystal_F_000             4536
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.00137(17)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1005
_refine_ls_number_reflns         12609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0691
_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^)+(0.0721P)^2^+11.8631P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1721
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8719
_reflns_number_total             12609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07617_si_001.cif
_cod_data_source_block           hje39
_cod_original_cell_volume        10714.1(15)
_cod_database_code               4132972
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4774(12) 0.5226(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C11A(H11A), C22A(H22A), C23A(H23A), C24A(H24A), C11B(H11B), C22B(H22B),
 C23B(H23B), C24B(H24B), C11C(H11C), C22C(H22C), C23C(H23C), C24C(H24C)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C9A(H9A), C13A(H13A),
 C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A), C20A(H20A), C29A(H29A),
 C30A(H30A), C31A(H31A), C32A(H32A), C2B(H2B), C4B(H4B), C5B(H5B), C6B(H6B),
 C7B(H7B), C9B(H9B), C13B(H13B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B),
  C20B(H20B), C29B(H29B), C30B(H30B), C31B(H31B), C32B(H32B), C2C(H2C),
 C4C(H4C), C5C(H5C), C6C(H6C), C7C(H7C), C9C(H9C), C13C(H13C), C15C(H15C),
 C16C(H16C), C17C(H17C), C18C(H18C), C20C(H20C), C29C(H29C), C30C(H30C),
 C31C(H31C), C32C(H32C)
3.c Idealised Me refined as rotating group:
 C33A(H33A,H33B,H33C), C33B(H33D,H33E,H33F), C33C(H33G,H33H,H33I)
;
_shelx_res_checksum              47295
_shelx_hkl_checksum              49006
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'