Metal-free graphene oxide-catalyzed aza-semipinacol rearrangement to prepare 2-(indol-2-yl)phenols and benzofuro[3,2-b]indolines containing quaternary carbon centers
Zhao, Hong-Ping; Liang, Gui-Chao; Nie, Shu-Min; Lu, Xiuqiang; Pan, Cheng-Xue; Zhong, Xin-Xian; Su, Gui-Fa; Mo, Dong-Liang; Green Chemistry 22 (2020) 404–410; doi:10.1039/C9GC03345A

data_7235236
_publ_section_title
;
 Metal-free graphene oxide-catalyzed aza-semipinacol rearrangement to
 prepare 2-(indol-2-yl)phenols and benzofuro[3,2-b]indolines containing
 quaternary carbon centers
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              404
_journal_page_last               410
_journal_paper_doi               10.1039/C9GC03345A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C23 H19 N O'
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-16 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.447(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.012(3)
_cell_length_b                   9.465(3)
_cell_length_c                   15.801(5)
_cell_measurement_reflns_used    4150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      2.51
_cell_volume                     1795.9(9)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21384
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.473
_diffrn_reflns_theta_min         2.104
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0628P)^2^+0.2965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2477
_reflns_number_total             3680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc03345a2.cif
_cod_data_source_block           aaaa
_cod_depositor_comments
;Adding full bibliography for 7235236.cif.

 Adding full bibliography for 7235236.cif.
;
_cod_original_cell_volume        1795.8(9)
_cod_database_code               7235236
_shelx_shelxl_version_number     2014/7
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00M), C00M(H00N),
 C00N(H00O), C00O(H00P), C00P(H00Q)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00K,H00L)
2.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              68640
_olex2_submission_special_instructions 'No special instructions were received'