Decreasing Aromaticity in π-Conjugated Materials: Efficient Synthesis and Electronic Structure Identification of Cyclopentadiene-Containing Systems
Chen, Lei; Mahmoud, Sufian M.; Yin, Xiaodong; Lalancette, Roger A.; Pietrangelo, Agostino; Organic Letters 15 (2013) 5970–; doi:10.1021/ol402824m

data_1513133
_publ_section_title
;
 Decreasing Aromaticity in \p-Conjugated Materials: Efficient Synthesis
 and Electronic Structure Identification of Cyclopentadiene-Containing
 Systems
;
_journal_issue                   23
_journal_name_full               'Organic Letters'
_journal_page_first              5970
_journal_paper_doi               10.1021/ol402824m
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H14 S2'
_chemical_formula_sum            'C15 H14 S2'
_chemical_formula_weight         258.40
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5615(1)
_cell_length_b                   21.1348(4)
_cell_length_c                   16.2978(3)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.89
_cell_measurement_theta_min      4.18
_cell_volume                     2604.56(8)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.024
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25090
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         71.97
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.470
_exptl_absorpt_correction_T_max  0.7408
_exptl_absorpt_correction_T_min  0.2432
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack (1983), 1962 Friedel pairs'
_refine_ls_abs_structure_Flack   0.036(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4487
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.024
_refine_ls_R_factor_gt           0.023
_refine_ls_shift/su_max          0.00
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.1423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.058
_refine_ls_wR_factor_ref         0.059
_reflns_number_gt                4337
_reflns_number_total             4487
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol402824m_si_002.cif
_cod_data_source_block           Th-C5-Th
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
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_cod_database_code               1513133