Intramolecular Electrophilic Cyclization Approach to 6-Substituted Naphtho[2,1- b]benzofurans: Novel Dual-State Emissive Fluorophores with Blue Emission.
Singh, Dileep Kumar; Jang, Kyungkuk; Kim, Jinhwang; Lee, Jeeyeon; Kim, Ikyon; ACS combinatorial science 21 (2019) 408–416; doi:10.1021/acscombsci.9b00006

data_4514905
_publ_section_title
;
 Intramolecular Electrophilic Cyclization Approach to 6-Substituted
 Naphtho[2,1- b]benzofurans: Novel Dual-State Emissive Fluorophores with
 Blue Emission.
;
_journal_issue                   5
_journal_name_full               'ACS combinatorial science'
_journal_page_first              408
_journal_page_last               416
_journal_paper_doi               10.1021/acscombsci.9b00006
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C21 H14 O2 S'
_chemical_formula_sum            'C21 H14 O2 S'
_chemical_formula_weight         330.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.688(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.72930(10)
_cell_length_b                   15.1954(3)
_cell_length_c                   18.1245(5)
_cell_measurement_reflns_used    3197
_cell_measurement_temperature    294.4(2)
_cell_measurement_theta_max      73.0770
_cell_measurement_theta_min      3.7770
_cell_volume                     1567.16(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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_environment      air
_diffrn_ambient_temperature      294.4(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -113.00 -14.00   1.00    1.37    --  -41.74 -57.00-120.00   99
  2  \w    -82.00  -5.00   1.00    1.37    --  -41.74 125.00   0.00   77
  3  \w    -79.00  -6.00   1.00    1.37    --  -41.74 125.00-150.00   73
  4  \w    -67.00  24.00   1.00    1.37    --  -41.74  57.00-180.00   91
  5  \w     89.00 126.00   1.00    5.48    --  106.19 -30.00 150.00   37
  6  \w    125.00 152.00   1.00    5.48    --  106.19  61.00 150.00   27
  7  \w     24.00  90.00   1.00    5.48    --  106.19 -94.00  30.00   66
  8  \w     80.00 176.00   1.00    5.48    --  106.19  61.00-180.00   96
  9  \w     74.00 114.00   1.00    5.48    --  106.19  77.00  30.00   40
 10  \w     39.00  87.00   1.00    5.48    --  106.19 -30.00 150.00   48
 11  \w     88.00 121.00   1.00    5.48    --  106.19-125.00   0.00   33
 12  \w     80.00 105.00   1.00    5.48    --  106.19  61.00 150.00   25
 13  \w     33.00 132.00   1.00    5.48    --  106.19 -45.00  30.00   99
 14  \w    107.00 167.00   1.00    5.48    --  106.19 125.00  90.00   60
 15  \w     83.00 160.00   1.00    5.48    --  106.19  15.00 150.00   77
 16  \w    146.00 171.00   1.00    5.48    --  106.19 125.00-150.00   25
 17  \w     30.00 124.00   1.00    5.48    --  106.19 -77.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1283931000
_diffrn_orient_matrix_UB_12      0.0885412000
_diffrn_orient_matrix_UB_13      0.0139861000
_diffrn_orient_matrix_UB_21      -0.1871118000
_diffrn_orient_matrix_UB_22      0.0297419000
_diffrn_orient_matrix_UB_23      0.0493056000
_diffrn_orient_matrix_UB_31      0.1477704000
_diffrn_orient_matrix_UB_32      -0.0393569000
_diffrn_orient_matrix_UB_33      0.0685416000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5079
_diffrn_reflns_point_group_measured_fraction_full 0.724
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.595
_diffrn_reflns_theta_min         3.807
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.908
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       irregular
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0601P)^2^+0.1944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.429
_reflns_Friedel_fraction_full    0.446
_reflns_Friedel_fraction_max     0.423
_reflns_number_gt                2140
_reflns_number_total             2220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            co9b00006_si_002.cif
_cod_data_source_block           exp_1256
_cod_database_code               4514905
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'c21 h14 o2 s'
_chemical_oxdiff_usercomment     6NP-7
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C21(H21), C15(H15), C16(H16), C6(H6), C5(H5), C24(H24),
 C4(H4), C23(H23)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              54023
_shelx_hkl_checksum              40812
_olex2_date_sample_data_collection 2018-06-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.681