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_4034701
_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         'C22 H13 N3 O2 S'
_chemical_formula_sum            'C22 H13 N3 O2 S'
_chemical_formula_weight         383.41
_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                72.261(2)
_cell_angle_beta                 78.663(2)
_cell_angle_gamma                80.202(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9887(2)
_cell_length_b                   10.3971(2)
_cell_length_c                   14.9094(4)
_cell_measurement_reflns_used    10216
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      67.3140
_cell_measurement_theta_min      3.1250
_cell_volume                     1004.63(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 0.967
_diffrn_measured_fraction_theta_max 0.967
_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   -360.00   9.50   0.50   10.00  11.97  34.50  35.50    --   739
  2  \f   -345.84  -0.34   0.50   10.00 154.98  94.50  35.50    --   691
  3  \f   -359.99   9.51   0.50   10.00-177.24 104.50  65.49    --   739
  4  \f      0.00 319.00   0.50   10.00  25.80 104.50 -59.50    --   638
  5  \f   -359.71   8.79   0.50   10.00 133.91 104.50 -89.50    --   737
  6  \w     76.39 187.89   0.50   10.00    --  104.50 125.48 -52.49  223
  7  \f   -338.68   9.32   0.50   10.00 123.85 102.00  70.49    --   696
  8  \w     28.50 108.01   0.50   10.00    --  107.00 -94.48 -77.52  159
  9  \w     31.10 146.10   0.50   10.00    --  102.00-169.42-147.57  230
 10  \f     38.32 320.32   0.50   10.00  98.66  57.00  30.50    --   564
 11  \f   -177.08   9.42   0.50   10.00  97.27  74.50  70.49    --   373
 12  \w     29.38 141.38   0.50   10.00    --   99.50-164.43  -0.06  224
 13  \w    -13.51  29.49   0.50   10.00    --   54.50 -69.49-170.01   86
 14  \w     67.93 131.43   0.50   10.00    --   52.00-169.42 114.93  127
 15  \w      8.66 112.66   0.50   10.00    --   99.50 -59.50 -32.50  208
 16  \w     90.41 165.41   0.50   10.00    --   99.50 165.40-169.92  150
 17  \w    125.12 184.12   0.50   10.00    --  102.00 110.49 -84.99  118
 18  \f   -350.27 -18.77   0.50   10.00-177.51 107.00  65.49    --   663
 19  \w     84.91 129.41   0.50   10.00    --   37.00 130.47  72.53   89
 20  \w     83.65 159.65   0.50   10.00    --  104.50  80.49-177.49  152
 21  \w     90.12 162.12   0.50   10.00    --   74.50 140.47 147.53  144
 22  \w     27.78  79.28   0.50   10.00    --   62.00 -74.48 127.49  103
 23  \w     18.16  94.16   0.50   10.00    --   44.50-139.46 119.97  152
 24  \f      0.01 275.01   0.50   10.00 148.50  62.00  65.49    --   550
 25  \w     59.37 134.37   0.50   10.00    --   89.50-159.43-145.06  150
 26  \w     32.71 142.71   0.50   10.00    --   62.00  55.50 145.01  220
 27  \w     69.72 145.22   0.50   10.00    --   57.00 170.38  15.10  151
 28  \f     12.52 197.02   0.50   10.00  86.63  97.00  35.50    --   369
 29  \w     33.62 116.62   0.50   10.00    --   99.50-159.43 -60.06  166
 30  \w     30.10 116.10   0.50   10.00    --  104.50 -69.49 -75.01  172
 31  \w     20.40 111.40   0.50   10.00    --   62.00-119.49 152.49  182
 32  \w     69.18 179.18   0.50   10.00    --  104.50  70.49  37.50  220
 33  \w     18.15 118.65   0.50   10.00    --  104.50-134.47-120.02  201
 34  \f     67.25 228.75   0.50   10.00   3.74  82.00 -64.49    --   323
 35  \w     16.07 119.07   0.50   10.00    --  104.50-134.47-107.52  206
 36  \w      0.70 114.70   0.50   10.00    --   92.00 -74.48-135.01  228
 37  \w     79.55 184.05   0.50   10.00    --  107.00 130.47  27.53  209
 38  \f   -218.81   9.19   0.50   10.00  19.89 104.50 -49.50    --   456
 39  \w     85.89 196.89   0.50   10.00    --  104.50 100.49  97.51  222
 40  \f    109.24 291.24   0.50   10.00 -22.75   2.00  80.49    --   364
 41  \f     45.64 315.64   0.50   10.00  60.66  99.50 -64.49    --   540
;
_diffrn_measurement_device       'Nonius KappaCCD Diffractometer'
_diffrn_measurement_device_type  'Nonius KappaCCD Diffractometer'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0340005000
_diffrn_orient_matrix_UB_12      -0.1527911000
_diffrn_orient_matrix_UB_13      0.0067866000
_diffrn_orient_matrix_UB_21      0.0034179000
_diffrn_orient_matrix_UB_22      0.0343958000
_diffrn_orient_matrix_UB_23      -0.1083401000
_diffrn_orient_matrix_UB_31      0.2238143000
_diffrn_orient_matrix_UB_32      0.0039726000
_diffrn_orient_matrix_UB_33      -0.0165053000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18791
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.546
_diffrn_reflns_theta_max         67.546
_diffrn_reflns_theta_min         3.150
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0599P)^2^+0.3895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3041
_reflns_number_total             3508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02523_si_003.cif
_cod_data_source_block           compound_6
_cod_database_code               4034701
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 97.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              76414
_shelx_hkl_checksum              85126
_shelx_fab_checksum              63236
_olex2_submission_special_instructions 'No special instructions were received'