A switchable redox annulation of 2-nitroarylethanols affording N-heterocycles: photoexcited nitro as a multifunctional handle
Wang, Bin; Ren, Hongyuan; Cao, Hou-Ji; Lu, Changsheng; Yan, Hong; Chemical Science 13 (2022) 11074–11082; doi:10.1039/D2SC03590A

data_1567551
_publ_section_title
;
 A switchable redox annulation of 2-nitroarylethanols affording
 N-heterocycles: photoexcited nitro as a multifunctional handle
;
_journal_issue                   37
_journal_name_full               'Chemical Science'
_journal_page_first              11074
_journal_page_last               11082
_journal_paper_doi               10.1039/D2SC03590A
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C34 H25 N'
_chemical_formula_sum            'C34 H25 N'
_chemical_formula_weight         447.55
_chemical_name_systematic        2-(4-(1,2,2-Triphenylvinyl)phenyl)-1H-indole
_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             2022-03-31
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-31 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.791(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9280(19)
_cell_length_b                   9.4716(18)
_cell_length_c                   52.455(10)
_cell_measurement_reflns_used    4697
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.29
_cell_volume                     4932.1(16)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_unetI/netI     0.1079
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       68
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            46913
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.083
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1039 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.8550.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_preparation
'Luminescent,Aggregation-Induced Emission (AIE)'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0077(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     632
_refine_ls_number_reflns         11557
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1877
_refine_ls_R_factor_gt           0.0702
_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^)+(0.1028P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1797
_refine_ls_wR_factor_ref         0.2298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4657
_reflns_number_total             11557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03590a2.cif
_cod_data_source_block           123_a
_cod_depositor_comments
'Adding full bibliography for 1567549--1567552.cif.'
_cod_original_cell_volume        4932.1(17)
_cod_database_code               1567551
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 N1-C6 \\sim N2-C41
 with sigma of 0.02
3. Rigid bond restraints
 N2, C41
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N2, C43
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C43) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C42) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
 C34(H34), N2(H2A), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C45(H45),
 C46(H46), C48(H48), C49(H49), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56),
  C59(H59), C60(H60), C61(H61), C62(H62), C63(H63), C66(H66), C67(H67),
 C68(H68), C69(H69), C70(H70)
;
_shelx_res_checksum              59837
_olex2_submission_special_instructions 'No special instructions were received'