Synthesis, characterization and unusual near-infrared luminescence of 1,1,4,4-tetracyanobutadiene derivatives.
Bui, Anh Thy; Philippe, Clotilde; Beau, Maxime; Richy, Nicolas; Cordier, Marie; Roisnel, Thierry; Lemiègre, Loïc; Mongin, Olivier; Paul, Frédéric; Trolez, Yann; Chemical communications (Cambridge, England) 56 (2020) 3571–3574; doi:10.1039/c9cc09560h

data_7126040
_publ_section_title
;
 Synthesis, characterization and unusual near-infrared luminescence of
 1,1,4,4-tetracyanobutadiene derivatives.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3571
_journal_page_last               3574
_journal_paper_doi               10.1039/c9cc09560h
_journal_volume                  56
_journal_year                    2020
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C32 H19 N5 O2 S'
_chemical_formula_sum            'C32 H19 N5 O2 S'
_chemical_formula_weight         537.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2019-11-20 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.987(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7660(9)
_cell_length_b                   26.272(2)
_cell_length_c                   11.5682(9)
_cell_measurement_reflns_used    9447
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5324
_cell_measurement_theta_min      2.4318
_cell_measurement_wavelength     0.71073
_cell_volume                     2503.7(4)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         2.919
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       prism
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0320P)^2^+1.6627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4411
_reflns_number_total             5619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc09560h2.cif
_cod_data_source_block           TCBDPYRENE
_cod_depositor_comments
'Adding full bibliography for 7126039--7126040.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7126040
_shelx_res_checksum              19001