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_1567550
_publ_section_title
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 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         'C16 H11 N O, [+ solvents]0.3[H2O]'
_chemical_formula_sum            'C16 H11 N O'
_chemical_formula_weight         233.26
_chemical_name_systematic        4-(Phenylethynyl)indolin-2-one
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_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
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   35.383(2)
_cell_length_b                   35.383(2)
_cell_length_c                   5.2350(4)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      53.89
_cell_measurement_theta_min      3.76
_cell_volume                     5675.9(6)
_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      193.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            21591
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.031
_diffrn_reflns_theta_min         2.173
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5699
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0708 after correction.
The Ratio of minimum to maximum transmission is 0.7593.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       needle
_exptl_crystal_F_000             2196
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0019(3)
_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   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0817P)^2^+9.2845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.1862
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2015
_reflns_number_total             2310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03590a2.cif
_cod_data_source_block           123_sq
_cod_depositor_comments
'Adding full bibliography for 1567549--1567552.cif.'
_cod_original_cell_volume        5675.8(8)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               1567550
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C4(H4), C16(H16), C15(H15), C14(H14), C13(H13),
 C12(H12)
2.c Fitted hexagon refined as free rotating group:
 C11(C16,C15,C14,C13,C12)
;
_shelx_res_checksum              33777
_shelx_fab_checksum              81181
_platon_squeeze_special_details
;
A solvent mask was calculated and 78 electrons were 
found in a volume of 263\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
[+ solvents]0.3[H2O] per Asymmetric Unit 
which account for 54 electrons 
per unit cell.
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'