Synthesis and structures of 11,11,12,12-tetracyano-2,6-diiodo-9,10-anthraquinodimethane and its 2:1 cocrystals with anthracene, pyrene and tetrathiafulvalene
Ren, Yi; Lee, Semin; Bertke, Jeffery; Gray, Danielle L.; Moore, Jeffrey S.; Acta Crystallographica Section C 72 (2016) 923–931; doi:10.1107/S2053229616016387

data_2020659
_publ_section_title
;
 Synthesis and structures of
 11,11,12,12-tetracyano-2,6-diiodo-9,10-anthraquinodimethane and its 2:1
 cocrystals with anthracene, pyrene and tetrathiafulvalene
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              923
_journal_page_last               931
_journal_paper_doi               10.1107/S2053229616016387
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          '2C20 H6 I2 N4, C6 H4 S4'
_chemical_formula_moiety         '2(C20 H6 I2 N4), C6 H4 S4'
_chemical_formula_sum            'C46 H16 I4 N8 S4'
_chemical_formula_weight         1326.50
_chemical_name_systematic
;
11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane--tetrathiafulvalene
(2/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                80.247(9)
_cell_angle_beta                 74.695(9)
_cell_angle_gamma                70.392(8)
_cell_formula_units_Z            1
_cell_length_a                   8.615(2)
_cell_length_b                   11.631(3)
_cell_length_c                   12.450(3)
_cell_measurement_reflns_used    9509
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.64
_cell_volume                     1129.0(5)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
<i>XPREP</i> (Bruker, 2014) and SADABS (Bruker, 2014)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2014) and OLEX2 (Dolomanov <i>et al.</i>,
2009)
;
_computing_publication_material
;
<i>XCIF</i> (Bruker, 2014)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker D8 Venture/Photon 100'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29346
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.201
_diffrn_reflns_theta_min         2.412
_exptl_absorpt_coefficient_mu    2.989
_exptl_absorpt_correction_T_max  0.97809
_exptl_absorpt_correction_T_min  0.92580
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.116
_refine_diff_density_max         1.714
_refine_diff_density_min         -1.199
_refine_ls_extinction_coef       0.0373(11)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0457P)^2^+2.8841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                4572
_reflns_number_total             4993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yo3023sup1.cif
_cod_data_source_block           III
_cod_depositor_comments
;
Adding full bibliography for 2020656--2020659.cif.

2019-10-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C20 H6 I2 N4, 0.5(C6 H4 S4)'
_cod_original_formula_iupac      'C20 H6 I2 N4, 0.5C6 H4 S4'
_cod_original_formula_sum        'C23 H8 I2 N4 S2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     658.25
_cod_database_code               2020659
_cod_database_fobs_code          2020659
_shelx_estimated_absorpt_t_min   0.343
_shelx_estimated_absorpt_t_max   0.723
_shelx_hkl_checksum              48203
_shelx_res_checksum              8216
_shelxl_version_number           2014/6