Synthesis of Emissive Heteroacene Derivatives via Nucleophilic Aromatic Substitution.
Hiscock, Lana K.; Yao, Chengzhang; Skene, William G.; Dawe, Louise N.; Maly, Kenneth Edward; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02523

data_4034702
_publ_section_title
;
 Synthesis of Emissive Heteroacene Derivatives via Nucleophilic Aromatic
 Substitution.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02523
_journal_year                    2019
_chemical_formula_moiety         'C24 H18 N4 S2'
_chemical_formula_sum            'C24 H18 N4 S2'
_chemical_formula_weight         426.54
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                80.705(4)
_cell_angle_beta                 79.917(5)
_cell_angle_gamma                89.967(5)
_cell_formula_units_Z            1
_cell_length_a                   5.1447(3)
_cell_length_b                   9.3119(5)
_cell_length_c                   10.5693(5)
_cell_measurement_reflns_used    8187
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      40.9750
_cell_measurement_theta_min      3.9760
_cell_volume                     491.78(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'Bruker Apex3'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \f   -256.13 113.38   0.50   39.99  22.01 -30.00-146.94    --   739
  2  \f   -361.06   7.94   0.50   40.01 -49.28 -45.00  26.20    --   738
  3  \f   -354.64   8.86   0.50   39.99 -83.59 -47.50  90.47    --   727
  4  \w     58.82 136.32   0.50   40.00    --   45.00-164.31  57.35  155
  5  \w     16.24 132.24   0.50   40.00    --   37.50  28.85  41.49  232
  6  \w    -11.33  34.67   0.50   40.00    --   22.50 -41.99 -82.50   92
  7  \w    -54.11  -5.11   0.50   40.00    --  -10.00  77.98 142.51   98
  8  \f   -118.94 250.56   0.50   40.00  -1.17 -52.50 -30.17    --   739
  9  \f      4.34 199.84   0.50   40.00 -65.79 -50.00 -30.17    --   391
 10  \f   -308.05   9.45   0.50   39.99 -89.64 -47.50 -61.99    --   635
;
_diffrn_measurement_device       'Bruker Apex II Diffractometer'
_diffrn_measurement_device_type  'Bruker Apex II Diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0208963000
_diffrn_orient_matrix_UB_12      0.0735236000
_diffrn_orient_matrix_UB_13      0.0080644000
_diffrn_orient_matrix_UB_21      0.0421190000
_diffrn_orient_matrix_UB_22      0.0225961000
_diffrn_orient_matrix_UB_23      -0.0678985000
_diffrn_orient_matrix_UB_31      -0.1319602000
_diffrn_orient_matrix_UB_32      -0.0067791000
_diffrn_orient_matrix_UB_33      -0.0099582000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10008
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_min         3.970
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       plate
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1055P)^2^+1.1002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1907
_refine_ls_wR_factor_ref         0.1964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1715
_reflns_number_total             1864
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02523_si_003.cif
_cod_data_source_block           compound_7
_cod_database_code               4034702
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              1576
_shelx_hkl_checksum              5500
_olex2_submission_special_instructions 'No special instructions were received'