An n–>pi^*^ interaction reduces the electrophilicity of the acceptor carbonyl group
Amit Choudhary; Charles G. Fry; Kimberli J. Kamer; Ronald T. Raines; Chem.Commun. 49 (2013) 8166–; doi:10.1039/c3cc44573a

data_7109727
_publ_section_title
;
 An n-->pi^*^ interaction reduces the electrophilicity of the acceptor
 carbonyl group
;
_journal_name_full               Chem.Commun.
_journal_page_first              8166
_journal_paper_doi               10.1039/c3cc44573a
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C9 H14 N2 O2 S2'
_chemical_formula_sum            'C9 H14 N2 O2 S2'
_chemical_formula_weight         246.34
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.830(3)
_cell_angle_beta                 93.213(3)
_cell_angle_gamma                91.152(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5152(3)
_cell_length_b                   7.2897(3)
_cell_length_c                   12.4680(5)
_cell_measurement_reflns_used    5112
_cell_measurement_temperature    107(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      1.67
_cell_volume                     580.41(4)
_computing_cell_refinement       'SAINT Ver. 7.24A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 Ver. 2.1-4 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT Ver. 7.24A'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXTL, OLEX2 (Dolomanov et al., 2009)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      107(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60\% \w and 0.6\% \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11000
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.9490
_exptl_absorpt_correction_T_min  0.9368
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.8650P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                2009
_reflns_number_total             2366
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c3cc44573a.txt
_cod_data_source_block           raines40
_cod_original_sg_symbol_Hall     '-P 1        '
_cod_original_sg_symbol_H-M      'P -1        '
_cod_database_code               7109727