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_4034699
_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         'C20 H8 N2 O4'
_chemical_formula_sum            'C20 H8 N2 O4'
_chemical_formula_weight         340.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.15370(10)
_cell_length_b                   19.3801(3)
_cell_length_c                   20.9999(4)
_cell_measurement_reflns_used    19131
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      67.2530
_cell_measurement_theta_min      3.0490
_cell_volume                     2911.41(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'SAINT (Bruker)'
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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   -348.13   3.87   0.50    8.00 -61.79  27.00 170.38    --   704
  2  \f   -359.72   3.78   0.50    8.00  36.73  57.00  25.50    --   727
  3  \f   -352.00   9.50   0.50    8.00  86.63  97.00  35.50    --   723
  4  \f   -342.68   9.32   0.50    8.00  60.66  99.50 -64.49    --   704
  5  \f   -359.92   9.58   0.50    8.00 153.69  99.50 165.40    --   739
  6  \f   -360.00   9.50   0.50    8.00 123.85 102.00  70.49    --   739
  7  \f   -357.47   8.53   0.50    8.00-177.51 107.00  65.49    --   732
  8  \f   -360.01   9.49   0.50    8.00  19.89 104.50 -49.50    --   739
  9  \w     13.22 106.22   0.50    8.00    --   62.00-109.48 174.99  186
 10  \w     15.50 108.01   0.50    8.00    --  107.00 -94.48 -77.52  185
 11  \w    119.91 165.41   0.50    8.00    --   99.50 165.40-169.92   91
 12  \f   -360.01   9.49   0.50    8.00 133.91 104.50 -89.50    --   739
 13  \w     55.80 108.80   0.50    8.00    --   44.50-139.46 119.97  106
 14  \w     80.96 113.46   0.50    8.00    --   37.00 115.48 -27.48   65
 15  \w    110.38 146.38   0.50    8.00    --   54.50  25.50 165.00   72
 16  \w     36.77  83.27   0.50    8.00    --   92.00 -74.48-135.01   93
 17  \w      9.84 129.34   0.50    8.00    --   97.00 -79.48  94.99  239
 18  \f    103.29 153.79   0.50    8.00  25.98 107.00-134.47    --   101
 19  \f      0.00  53.50   0.50    8.00  97.27  74.50  70.49    --   107
 20  \w     33.75 106.25   0.50    8.00    --   77.00-174.28 172.32  145
 21  \w     26.31 108.31   0.50    8.00    --   57.00  40.50 -70.00  164
 22  \w     61.60 146.10   0.50    8.00    --  102.00-169.42-147.57  169
 23  \w     85.89 196.89   0.50    8.00    --  104.50 100.49  97.51  222
 24  \w     73.45 188.45   0.50    8.00    --  107.00 130.47  27.53  230
 25  \f     -0.01 185.49   0.50    8.00  27.31 102.00 -99.48    --   371
 26  \w     86.29 178.79   0.50    8.00    --   87.00 145.47  95.02  185
 27  \w     76.35 162.35   0.50    8.00    --  104.50 125.48 -52.49  172
 28  \w     83.39 174.39   0.50    8.00    --   82.00  80.49 -59.99  182
 29  \w     16.07 119.07   0.50    8.00    --  104.50-134.47-107.52  206
 30  \w     47.26 146.76   0.50    8.00    --   67.00  65.49 -77.49  199
 31  \w     16.07 119.07   0.50    8.00    --  104.50-134.47-120.02  206
 32  \f      0.01 108.51   0.50    8.00  52.49  39.50  45.49    --   217
 33  \w     83.39 196.89   0.50    8.00    --  104.50  80.49-177.49  227
 34  \w     18.15 131.65   0.50    8.00    --   97.00 -64.49 -87.51  227
 35  \w     26.54 137.54   0.50    8.00    --   99.50-159.43 -60.06  222
 36  \w     14.93 140.43   0.50    8.00    --  104.50 -69.49 -75.01  251
 37  \f     15.82 180.82   0.50    8.00  63.56  79.50-104.48    --   330
 38  \f      0.00 196.00   0.50    8.00 160.46  77.00  85.49    --   392
 39  \f     79.81 301.31   0.50    8.00 130.47  94.50  25.50    --   443
 40  \f   -360.00   9.50   0.50    8.00  25.80 104.50 -59.50    --   739
 41  \f   -360.01   9.49   0.50    8.00  22.01  54.50 -79.48    --   739
 42  \f   -359.00   9.00   0.50    8.00  66.62  37.00 -49.50    --   736
;
_diffrn_measurement_device       Nonius
_diffrn_measurement_device_type  Nonius
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0524185000
_diffrn_orient_matrix_UB_12      0.0760472000
_diffrn_orient_matrix_UB_13      -0.0117480000
_diffrn_orient_matrix_UB_21      -0.0598971000
_diffrn_orient_matrix_UB_22      0.0180434000
_diffrn_orient_matrix_UB_23      0.0684512000
_diffrn_orient_matrix_UB_31      0.2001052000
_diffrn_orient_matrix_UB_32      -0.0145054000
_diffrn_orient_matrix_UB_33      0.0236205000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52409
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.575
_diffrn_reflns_theta_max         67.575
_diffrn_reflns_theta_min         4.211
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60352
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       needle
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.405
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.363
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0671
_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^)+(0.0477P)^2^+2.9066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1511
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2522
_reflns_number_total             2604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02523_si_003.cif
_cod_data_source_block           compound_1
_cod_database_code               4034699
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.46
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16)
;
_shelx_res_checksum              4235
_shelx_hkl_checksum              7417
_olex2_submission_special_instructions 'No special instructions were received'