A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ): charge-transfer chromophores by [2 + 2] cycloaddition with alkynes.
Kivala, Milan; Boudon, Corinne; Gisselbrecht, Jean-Paul; Seiler, Paul; Gross, Maurice; Diederich, François; Chemical communications (Cambridge, England)  (2007) 4731–4733; doi:10.1039/b713683h

data_7102298
_publ_section_title
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 A novel reaction of 7,7,8,8-tetracyanoquinodimethane (TCNQ):
 charge-transfer chromophores by [2 + 2] cycloaddition with alkynes.
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_journal_issue                   45
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4731
_journal_page_last               4733
_journal_paper_doi               10.1039/b713683h
_journal_year                    2007
_chemical_formula_moiety         '3(C28 H19 N5),1.5(C2 H2 Cl4)'
_chemical_formula_sum            'C87 H60 Cl6 N15'
_chemical_formula_weight         1528.20
_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                82.970(11)
_cell_angle_beta                 85.747(12)
_cell_angle_gamma                81.416(11)
_cell_formula_units_Z            2
_cell_length_a                   11.1429(14)
_cell_length_b                   16.3191(15)
_cell_length_c                   22.2110(17)
_cell_measurement_reflns_used    27208
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.92
_cell_measurement_theta_min      2.95
_cell_volume                     3957.2(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Kappa CCD'
_computing_data_reduction        'Denzo + Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP (Johnson,1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et Al., 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full .982
_diffrn_measured_fraction_theta_max .982
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0820
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18424
_diffrn_reflns_theta_full        22.92
_diffrn_reflns_theta_max         22.92
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut fragment'
_exptl_crystal_F_000             1578
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         .723
_refine_diff_density_min         -.846
_refine_diff_density_rms         .088
_refine_ls_extinction_coef       0.0058(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     980
_refine_ls_number_reflns         10703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.1514
_refine_ls_R_factor_gt           0.1106
_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 w=1/[\s^2^(Fo^2^)+(0.1773P)^2^+15.5674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2882
_refine_ls_wR_factor_ref         0.3257
_reflns_number_gt                7198
_reflns_number_total             10703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b713683h.txt
_cod_data_source_block           kivala16t_D_07
_cod_depositor_comments
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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 
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_cod_database_code               7102298