Synthesis of a quinoidal dithieno[2,3-d;2′,3′-d]benzo[2,1-b;3,4-b′]-dithiophene based open-shell singlet biradicaloid
Xia, Debin; Keerthi, Ashok; An, Cunbin; Baumgarten, Martin; Organic Chemistry Frontiers 4 (2017) 18–; doi:10.1039/C6QO00543H

data_1553565
_publ_section_title
;
 Synthesis of a quinoidal
 dithieno[2,3-d;2&#x2032;,3&#x2032;-d]benzo[2,1-b;3,4-b&#x2032;]-dithiophene
 based open-shell singlet biradicaloid
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              18
_journal_paper_doi               10.1039/C6QO00543H
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C44 H52 N4 S4'
_chemical_formula_sum            'C44 H52 N4 S4'
_chemical_formula_weight         765.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-07-21 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                78.225(8)
_cell_angle_beta                 84.998(8)
_cell_angle_gamma                75.520(8)
_cell_formula_units_Z            2
_cell_length_a                   9.3265(10)
_cell_length_b                   9.7095(9)
_cell_length_c                   23.593(2)
_cell_measurement_reflns_used    11801
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      67.67
_cell_measurement_theta_min      3.83
_cell_volume                     2023.6(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      ' 983 frames, detector distance = 40 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'X-ray mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1181
_diffrn_reflns_av_unetI/netI     0.2211
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21362
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.617
_diffrn_reflns_theta_max         67.617
_diffrn_reflns_theta_min         3.830
_diffrn_source                   'Incoatec microSource Cu'
_exptl_absorpt_coefficient_mu    2.427
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_correction_T_min  0.7723
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2'
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.802
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         6932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.802
_refine_ls_R_factor_all          0.1924
_refine_ls_R_factor_gt           0.0676
_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^)+(0.0913P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.2042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2517
_reflns_number_total             6932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00543h2.cif
_cod_data_source_block           4CN-T
_cod_original_cell_volume        2023.6(4)
_cod_database_code               1553565
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.697
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              29437
_shelx_hkl_checksum              50364