NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives.
Ji, Hong; Zou, Juan; Mou, Chengli; Liu, Yonggui; Ren, Shi-Chao; Chi, Yonggui Robin; Chemical communications (Cambridge, England) 59 (2023) 6351–6354; doi:10.1039/d3cc00999h

data_7131559
_publ_section_title
;
 NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to
 indole derivatives.
;
_journal_issue                   42
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6351
_journal_page_last               6354
_journal_paper_doi               10.1039/d3cc00999h
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H18 Br N2 O3, C H2 Cl2'
_chemical_formula_sum            'C28 H20 Br Cl2 N2 O3'
_chemical_formula_weight         583.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-01-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2023-02-24 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.824(5)
_cell_length_b                   14.724(9)
_cell_length_c                   17.133(10)
_cell_measurement_reflns_used    3666
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      72.49
_cell_measurement_theta_min      3.00
_cell_volume                     2478(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16610
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         88.739
_diffrn_reflns_theta_min         3.959
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.530
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.2325
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1686 before and 0.1094 after correction.
The Ratio of minimum to maximum transmission is 0.3085.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       needle
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.259
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.165
_refine_ls_abs_structure_details
;
 Flack x determined using 1524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.202(10)
_refine_ls_extinction_coef       0.0142(15)
_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   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4705
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0911
_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^)+(0.1082P)^2^+17.5956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2399
_refine_ls_wR_factor_ref         0.2537
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.898
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                4198
_reflns_number_total             4705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00999h2.cif
_cod_data_source_block           20221228jh_0m_a
_cod_depositor_comments          'Adding full bibliography for 7131559.cif.'
_cod_database_code               7131559
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.636
_shelx_estimated_absorpt_t_min   0.612
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N008) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C00S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C009) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C00B(H00B)
3.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00C), C00J(H00F,H00G), C010(H01A,H01B)
3.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00K(H00K), C00I(H00I), C00D(H00D), C00T(H00T), C00R(H00R),
 C00V(H00V), C00O(H00O), C00X(H00X), C00N(H00N), C00W(H00W), C00Y(H00Y),
 C00Z(H00Z)
3.d Fitted hexagon refined as free rotating group:
 C00F(C00E,C009,C00A,C00K,C00I), C00G(C00C,C00D,C00T,C00R,C00V), C00X(C00N,
 C00P,C00W,C00Y,C00Z)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              49506
_shelx_hkl_checksum              98845
_olex2_submission_special_instructions 'No special instructions were received'