Bimetallic copper/cobalt-cocatalyzed double aerobic phenol oxidation/cyclization toward π-extended benzofuro[2,3-b]indoles as electron donors for electroluminescence
Bashir, Muhammad Adnan; Zhang, Yulong; Yu, Huaibin; Wang, Bofei; Zhao, Weining; Zhong, Fangrui; Green Chemistry 23 (2021) 5031–5036; doi:10.1039/D1GC01658J

data_7243065
_publ_section_title
;
 Bimetallic copper/cobalt-cocatalyzed double aerobic phenol
 oxidation/cyclization toward \p-extended benzofuro[2,3-b]indoles as
 electron donors for electroluminescence
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              5031
_journal_page_last               5036
_journal_paper_doi               10.1039/D1GC01658J
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C16 H11 N O4'
_chemical_formula_sum            'C16 H11 N O4'
_chemical_formula_weight         281.26
_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             2020-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-21 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.5170(2)
_cell_length_b                   6.91820(10)
_cell_length_c                   38.2895(4)
_cell_measurement_reflns_used    12823
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4270
_cell_measurement_theta_min      3.3110
_cell_volume                     4905.05(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.989
_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  \w    -54.00 -29.00   0.50    0.50    --    0.00  -9.00  87.00   50
  2  \w    100.00 125.00   0.50    0.50    --   94.60   9.00 -98.00   50
  3  \w     65.00  96.00   0.50    0.50    --   94.60  -9.00  87.00   62
  4  \w    -33.00   4.00   0.50    0.50    --    0.00 -82.00 120.00   74
  5  \w    -33.00   7.00   0.50    0.50    --    0.00 -82.00-180.00   80
  6  \w    -28.00  20.00   0.50    0.50    --    0.00 -82.00  60.00   96
  7  \w     91.00 165.00   0.50    0.50    --   94.60  82.00  90.00  148
  8  \w     42.00 124.00   0.50    0.50    --   94.60 -77.00-180.00  164
  9  \w      5.00 111.00   0.50    0.50    --   94.60 -30.00 150.00  212
 10  \w     53.00 100.00   0.50    0.50    --   94.60 -77.00 -90.00   94
 11  \w      5.00  30.00   0.50    0.50    --   94.60 -77.00-180.00   50
 12  \w    159.00 184.00   0.50    0.50    --   94.60  82.00 120.00   50
 13  \w    108.00 133.00   0.50    0.50    --   94.60  82.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0783144000
_diffrn_orient_matrix_UB_12      0.0258093000
_diffrn_orient_matrix_UB_13      0.0127477000
_diffrn_orient_matrix_UB_21      0.0265966000
_diffrn_orient_matrix_UB_22      -0.0023397000
_diffrn_orient_matrix_UB_23      -0.0381283000
_diffrn_orient_matrix_UB_31      -0.0088950000
_diffrn_orient_matrix_UB_32      0.2211360000
_diffrn_orient_matrix_UB_33      -0.0018721000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            20065
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.808
_diffrn_reflns_theta_min         3.320
_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  0.40011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+2.1728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4510
_reflns_number_total             4810
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1gc01658j2.cif
_cod_data_source_block           20200628_1
_cod_depositor_comments          'Adding full bibliography for 7243065.cif.'
_cod_database_code               7243065
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.00
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N0AA(H0AA), C0BA(H0BA), C1BA(H1BA), C5(H5), C12(H12), C2(H2A),
 C11(H11), C1AA(H1AB), C3(H3), C4AA(H4AA), C4(H4), C2AA(H2AA), C3AA(H3AA)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C5BA(H5BA,H5BB,H5BC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1AA(H1AA), O2(H2)
;
_shelx_res_checksum              32391
_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 1.777
_oxdiff_exptl_absorpt_empirical_full_min 0.561