A Highly Electron-Deficient Analogue of Aniline, Soluble Oligomers, and Their Redox Properties
Brandon Djukic; Alan J. Lough; Dwight S. Seferos; Journal of Organic Chemistry 78 (2013) 9340–9344; doi:10.1021/jo401565f

data_4028620
_publ_section_title
;
 A Highly Electron-Deficient Analogue of Aniline, Soluble Oligomers, and
 Their Redox Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9340
_journal_page_last               9344
_journal_paper_doi               10.1021/jo401565f
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C9 H14 N2 O S, C6 H14'
_chemical_formula_sum            'C15 H28 N2 O S'
_chemical_formula_weight         284.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.627(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   35.432(7)
_cell_length_b                   13.899(3)
_cell_length_c                   5.4329(13)
_cell_measurement_reflns_used    4380
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.26
_cell_volume                     2674.5(10)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10752
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         1.15
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_platon_squeeze_details
; 
During the 
refinement of the structure, electron density peaks were located 
that were believed to be highly disordered 
solvent molecules (hexane). Attempts 
made to model the solvent molecule were not successful. 
The SQUEEZE option in PLATON (Spek, 2003) indicated there was a 
total solvent cavity 678e/A3 per unit cell. In the final cycles of 
refinement, the contribution of 305 electrons to the 
electron density was removed from the observed data. The 
density, the F(000) value, the molecular weight and the formula are 
given taking into account the results obtained with the 
SQUEEZE option PLATON (Spek, 2003).
;
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3063
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0752P)^2^+3.1400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1670
_reflns_number_gt                2286
_reflns_number_total             3063
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo401565f_si_002_2.cif
_cod_data_source_block           d1346
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4028620