Dinitro and Quinodimethane Derivatives of Terthiophene That Can Be Both Oxidized and Reduced. Crystal Structures, Spectra, and a Method for Analyzing Quinoid Contributions to Structure
Ted M. Pappenfus; Jonathan D. Raff; Eric J. Hukkanen; Jason R. Burney; Juan Casado; Steven M. Drew; Larry L. Miller; Kent R. Mann; Journal of Organic Chemistry 67 (2002) 6015–6024; doi:10.1021/jo025572b

data_4022223
_publ_section_title
;
 Dinitro and Quinodimethane Derivatives of Terthiophene
 That Can Be Both Oxidized and Reduced.
 Crystal Structures, Spectra, and a Method for Analyzing
 Quinoid Contributions to Structure
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6015
_journal_page_last               6024
_journal_paper_doi               10.1021/jo025572b
_journal_volume                  67
_journal_year                    2002
_chemical_formula_moiety         'C20 H22 N2 O4 S3'
_chemical_formula_sum            'C20 H22 N2 O4 S3'
_chemical_formula_weight         450.58
_chemical_name_common            01125
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                118.688(15)
_cell_angle_beta                 97.820(18)
_cell_angle_gamma                91.649(17)
_cell_formula_units_Z            2
_cell_length_a                   8.9514(15)
_cell_length_b                   11.434(2)
_cell_length_c                   11.871(3)
_cell_measurement_reflns_used    514
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      50.028
_cell_measurement_theta_min      5.552
_cell_volume                     1049.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Siemans SMART Platform CCD'
_diffrn_measurement_method       'Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6779
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.9413
_exptl_absorpt_correction_T_min  0.8841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc 
 [0.00000+1.00000exp(2.00(sin\q/\l)^2^)]/ 
   [\s^2^(Fo^2^)+0.0000+0.0500*P+(0.0449P)^2^+0.0000sin\q/\l] 
 where P = 0.33333Fo^2^ + 0.66667Fc^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                2879
_reflns_number_total             4655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo025572b_s1.cif
_cod_data_source_block           01125
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'Multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4022223