DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran (Thiophene).
Wang, Zheng-Lin; Li, Hong-Liang; Ge, Li-Shi; An, Xing-Lan; Zhang, Zi-Gang; Luo, Xiaoyan; Fossey, John S.; Deng, Wei-Ping; The Journal of organic chemistry 79 (2014) 1156–; doi:10.1021/jo4026034

data_4029014
_publ_section_title
;
 DDQ-Mediated Oxidative Coupling: An Approach to 2,3-Dicyanofuran
 (Thiophene).
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1156
_journal_paper_doi               10.1021/jo4026034
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C10 H10 N2 O4'
_chemical_formula_weight         222.20
_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                75.924(5)
_cell_angle_beta                 79.636(6)
_cell_angle_gamma                71.112(6)
_cell_formula_units_Z            2
_cell_length_a                   7.107(2)
_cell_length_b                   7.758(2)
_cell_length_c                   10.620(3)
_cell_measurement_reflns_used    1180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.351
_cell_measurement_theta_min      5.661
_cell_volume                     534.1(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0477
_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       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3047
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30135
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.065(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1231P)^2^+0.1574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2092
_reflns_number_gt                1516
_reflns_number_total             1965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4026034_si_004.cif
_cod_data_source_block           cd213311
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029014