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_1567552
_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         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-06
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-06 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.174(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   14.0103(13)
_cell_length_b                   35.603(3)
_cell_length_c                   11.3760(13)
_cell_measurement_reflns_used    5724
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.31
_cell_volume                     5048.1(9)
_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 0.991
_diffrn_measured_fraction_theta_max 0.990
_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  0.0653
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23828
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         2.011
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6024
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1418 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.8079.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.0029(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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         8815
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0729
_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^)+(0.1309P)^2^+3.1219P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2247
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                6420
_reflns_number_total             8815
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03590a2.cif
_cod_data_source_block           123_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1567549--1567552.cif.'
_cod_database_code               1567552
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C41(H41A,H41B), C62(H62A,H62B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C7(H7), C10(H10), C12(H12), C14(H14), C17(H17),
 N2(H2), C25(H25), C26(H26), C28(H28), C31(H31), C33(H33), C35(H35), C38(H38),
 N3(H3), C46(H46), C47(H47), C49(H49), C52(H52), C54(H54), C56(H56), C59(H59)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C42(H42A,H42B,H42C), C57(H57A,H57B,H57C), C58(H58A,
 H58B,H58C), C63(H63A,H63B,H63C)
;
_shelx_res_checksum              180
_olex2_submission_special_instructions 'No special instructions were received'