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_7126039
_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         'C36 H21 N5 O2 S'
_chemical_formula_sum            'C36 H21 N5 O2 S'
_chemical_formula_weight         587.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-11-20 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.551(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1162(16)
_cell_length_b                   7.7907(9)
_cell_length_c                   42.350(5)
_cell_measurement_reflns_used    9734
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.5029
_cell_measurement_theta_min      2.3799
_cell_measurement_wavelength     0.71073
_cell_volume                     5647.0(11)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'PLATON, A.L.Spek, Acta Cryst. 2009, D65, 148-155'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0217659
_diffrn_orient_matrix_UB_12      -0.0107357
_diffrn_orient_matrix_UB_13      -0.0008766
_diffrn_orient_matrix_UB_21      0.0001958
_diffrn_orient_matrix_UB_22      0.1258550
_diffrn_orient_matrix_UB_23      -0.0112823
_diffrn_orient_matrix_UB_31      0.0091554
_diffrn_orient_matrix_UB_32      0.0228316
_diffrn_orient_matrix_UB_33      0.0617793
_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  0.0367
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            24755
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.380
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.793
_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    1.382
_exptl_crystal_description       prism
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.780
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0729P)^2^+3.8822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5546
_reflns_number_total             6476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc09560h2.cif
_cod_data_source_block           CP1_111
_cod_depositor_comments
'Adding full bibliography for 7126039--7126040.cif.'
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               7126039
_shelx_res_checksum              99791