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_2020656
_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_coeditor_code           YO3023
_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          'C20 H6 I2 N4'
_chemical_formula_moiety         'C20 H6 I2 N4'
_chemical_formula_sum            'C20 H6 I2 N4'
_chemical_formula_weight         556.09
_chemical_name_systematic
;
11,11,12,12-Tetracyano-2,6-diiodo-9,10-anthraquinodimethane
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7660(3)
_cell_length_b                   12.2655(4)
_cell_length_c                   16.4903(6)
_cell_measurement_reflns_used    9591
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.47
_cell_volume                     1773.03(11)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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  0.0323
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20684
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.153
_diffrn_reflns_theta_min         2.470
_exptl_absorpt_coefficient_mu    3.558
_exptl_absorpt_correction_T_max  0.99957
_exptl_absorpt_correction_T_min  0.99892
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.815
_refine_ls_abs_structure_details
;
Flack (1983), with 1893 Friedel pairs
;
_refine_ls_abs_structure_Flack   -0.016(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0189
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+0.2251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0450
_reflns_number_gt                3849
_reflns_number_total             3929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yo3023sup1.cif
_cod_data_source_block           DITCAQ
_cod_depositor_comments
'Adding full bibliography for 2020656--2020659.cif.'
_cod_database_code               2020656
_cod_database_fobs_code          2020656
_shelx_estimated_absorpt_t_min   0.503
_shelx_estimated_absorpt_t_max   0.720
_shelx_hkl_checksum              65152
_shelx_res_checksum              76633
_shelxl_version_number           2014/6