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_4034700
_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         'C40 H50 N4 O2'
_chemical_formula_sum            'C40 H50 N4 O2'
_chemical_formula_weight         618.84
_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                81.525(2)
_cell_angle_beta                 83.346(3)
_cell_angle_gamma                82.899(2)
_cell_formula_units_Z            1
_cell_length_a                   7.2788(2)
_cell_length_b                   8.7498(2)
_cell_length_c                   13.4900(5)
_cell_measurement_reflns_used    5240
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      66.6570
_cell_measurement_theta_min      5.1160
_cell_volume                     839.07(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 0.966
_diffrn_measured_fraction_theta_max 0.966
_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   -356.93   2.07   0.50   10.00  51.30  52.00 -54.49    --   718
  2  \f     -0.01 358.49   0.50   10.00  10.36  67.00 -29.50    --   717
  3  \f   -360.01   9.49   0.50   10.00  60.66  99.50 -64.49    --   739
  4  \f   -360.01   9.49   0.50   10.00  19.89 104.50 -49.50    --   739
  5  \f   -360.00   9.50   0.50   10.00 123.85 102.00  70.49    --   739
  6  \f   -359.77   6.73   0.50   10.00-177.51 107.00  65.49    --   733
  7  \w     73.45 188.45   0.50   10.00    --  107.00 130.47  27.53  230
  8  \f     65.99 276.49   0.50   10.00  70.98  87.00 -99.48    --   421
  9  \f   -360.01   9.49   0.50   10.00 133.91 104.50 -89.50    --   739
 10  \w    115.91 165.41   0.50   10.00    --   99.50 165.40-169.92   99
 11  \f   -303.44   5.06   0.50   10.00  52.49  39.50  45.49    --   617
 12  \f     91.41 198.41   0.50   10.00 107.49  29.50-169.42    --   214
 13  \w    161.39 196.89   0.50   10.00    --  104.50 100.49  97.51   71
 14  \w    -59.06 -26.06   0.50   10.00    --   -8.00 120.49  92.51   66
 15  \w   -106.45 -70.45   0.50   10.00    --  -18.00 170.38  95.10   72
 16  \w     54.75 115.25   0.50   10.00    --   92.00 -74.48-135.01  121
 17  \f    231.87 274.87   0.50   10.00  25.98 107.00-134.47    --    86
 18  \w     70.68 141.68   0.50   10.00    --   77.00-174.28 172.32  142
 19  \w     12.02  76.52   0.50   10.00    --   34.50  40.50  42.50  129
 20  \w     83.76 152.26   0.50   10.00    --   72.00 145.47  20.02  137
 21  \w      9.59 107.09   0.50   10.00    --   99.50 -59.50 -32.50  195
 22  \w     16.07 119.07   0.50   10.00    --  104.50-134.47-120.02  206
 23  \w      5.52 136.02   0.50   10.00    --   97.00 -79.48  94.99  261
 24  \w     28.64 100.64   0.50   10.00    --   44.50-119.49-162.51  144
 25  \w     48.27 118.27   0.50   10.00    --   57.00  40.50 -70.00  140
 26  \w     15.54 102.04   0.50   10.00    --  107.00 -94.48 -77.52  173
 27  \w     83.39 196.89   0.50   10.00    --  104.50  80.49-177.49  227
 28  \w     30.03 127.53   0.50   10.00    --   99.50-159.43 -60.06  195
 29  \w     61.50 164.00   0.50   10.00    --   79.50  30.50 -27.50  205
 30  \w     78.05 191.55   0.50   10.00    --  104.50 125.48 -52.49  227
 31  \w     -7.75  83.25   0.50   10.00    --   72.00 -74.48   4.99  182
 32  \w     31.10 146.10   0.50   10.00    --  102.00-169.42-147.57  230
 33  \w     12.93 140.43   0.50   10.00    --  104.50 -69.49 -75.01  255
 34  \w     53.47 146.47   0.50   10.00    --   59.50 160.46 170.03  186
 35  \f     -0.01 286.49   0.50   10.00  66.62  37.00 -49.50    --   573
 36  \w     16.07 119.07   0.50   10.00    --  104.50-134.47-107.52  206
 37  \w     84.04 194.04   0.50   10.00    --  102.00 110.49 -84.99  220
 38  \f    -95.63   9.37   0.50   10.00  85.72 102.00 100.49    --   210
 39  \f   -338.40   8.53   0.50   10.00 123.53  94.50  30.50    --   693
 40  \f   -359.66   2.84   0.50   10.00  25.80 104.50 -59.50    --   725
;
_diffrn_measurement_device       'Nonius CCD'
_diffrn_measurement_device_type  'Nonius CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2049550000
_diffrn_orient_matrix_UB_12      -0.0461891000
_diffrn_orient_matrix_UB_13      0.0199592000
_diffrn_orient_matrix_UB_21      -0.0619134000
_diffrn_orient_matrix_UB_22      -0.0585793000
_diffrn_orient_matrix_UB_23      0.1107527000
_diffrn_orient_matrix_UB_31      -0.0103046000
_diffrn_orient_matrix_UB_32      -0.1627895000
_diffrn_orient_matrix_UB_33      -0.0282858000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15321
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.480
_diffrn_reflns_theta_max         67.480
_diffrn_reflns_theta_min         5.141
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97829
_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            red
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       plate
_exptl_crystal_F_000             334
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0600P)^2^+0.1811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2138
_reflns_number_total             2933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02523_si_003.cif
_cod_data_source_block           compound_4c
_cod_database_code               4034700
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 96.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.37
_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), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
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:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              18031
_shelx_hkl_checksum              86580
_olex2_submission_special_instructions 'No special instructions were received'