K<sub>2</sub>CO<sub>3</sub>-mediated annulation of 1,3-acetonedicarboxylates with 2-fluoro-1-nitroarenes: synthesis of indoles.
Chang, Meng-Yang; Ho, Chin-Huey; Chen, Hsing-Yin; Organic & biomolecular chemistry 22 (2024) 4108–4122; doi:10.1039/d4ob00488d

data_7159936
_publ_section_title
;
 K<sub>2</sub>CO<sub>3</sub>-mediated annulation of
 1,3-acetonedicarboxylates with 2-fluoro-1-nitroarenes: synthesis of
 indoles.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4108
_journal_page_last               4122
_journal_paper_doi               10.1039/d4ob00488d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H12 Cl2 N2 O3'
_chemical_formula_sum            'C18 H12 Cl2 N2 O3'
_chemical_formula_weight         375.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                68.739(2)
_cell_angle_beta                 77.265(2)
_cell_angle_gamma                87.293(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2481(2)
_cell_length_b                   10.2725(2)
_cell_length_c                   10.6752(2)
_cell_measurement_reflns_used    13779
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8030
_cell_measurement_theta_min      2.0940
_cell_volume                     821.66(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -23.00 100.00   0.50    1.11    --   10.60  50.00 -26.00  246
  2  \w    -79.00  44.00   0.50    1.11    --   10.60 -50.00-172.00  246
  3  \w    -44.00  78.00   0.50    1.11    --  -10.90  50.00 -26.00  244
  4  \w   -100.00  22.00   0.50    1.11    --  -10.90 -50.00-172.00  244
  5  \w    -17.00 100.00   0.50    1.11    --   10.60  82.00  90.00  234
  6  \w    -17.00 100.00   0.50    1.11    --   10.60  82.00  30.00  234
  7  \w    -17.00 100.00   0.50    1.11    --   10.60  82.00 -90.00  234
  8  \w    -17.00 100.00   0.50    1.11    --   10.60  82.00   0.00  234
  9  \w    -42.00  34.00   0.50    1.11    --   10.60 -82.00 127.72  152
 10  \w    -71.00 -45.00   0.50    1.11    --   10.60 -37.00-150.00   52
 11  \w    -19.00  16.00   0.50    1.11    --   10.60 -37.00-150.00   70
 12  \w     15.00 100.00   0.50    1.11    --   10.60  77.00-150.00  170
 13  \w    -17.00  33.00   0.50    1.11    --   10.60  82.00-120.00  100
 14  \w     75.00 100.00   0.50    1.11    --   10.60  82.00-120.00   50
 15  \w     -5.00 100.00   0.50    1.11    --   10.60  82.00 -60.00  210
 16  \w    -44.00  17.00   0.50    1.11    --  -10.90 -82.00  30.00  122
 17  \w   -100.00   8.00   0.50    1.11    --  -10.90 -82.00 150.00  216
 18  \w    -82.00 -47.00   0.50    1.11    --  -10.90 -77.00  90.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0573779000
_diffrn_orient_matrix_UB_12      -0.0530358000
_diffrn_orient_matrix_UB_13      0.0075231000
_diffrn_orient_matrix_UB_21      0.0436604000
_diffrn_orient_matrix_UB_22      -0.0504124000
_diffrn_orient_matrix_UB_23      0.0445224000
_diffrn_orient_matrix_UB_31      -0.0508393000
_diffrn_orient_matrix_UB_32      0.0119342000
_diffrn_orient_matrix_UB_33      0.0574360000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22394
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.044
_diffrn_reflns_theta_min         2.098
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     402
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0517P)^2^+0.4544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1031
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3060
_reflns_number_total             3443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00488d3.cif
_cod_data_source_block           k11211-myc-g(chnf3047)_auto
_cod_depositor_comments
'Adding full bibliography for 7159934--7159937.cif.'
_cod_original_cell_volume        821.67(3)
_cod_database_code               7159936
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.819
_shelx_estimated_absorpt_t_min   0.819
_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. Uiso/Uaniso restraints and constraints
C6 \\sim C15 \\sim C14 \\sim C7 \\sim C12 \\sim C1 \\sim C13 \\sim C5 \\sim C9
\\sim C8 \\sim C2 \\sim C4 \\sim C10 \\sim C16 \\sim C3 \\sim C11 \\sim C17
\\sim C18: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 3.8A
3.a Secondary CH2 refined with riding coordinates:
 C17(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H005), C9(H00G), C8(H00H), C2(H00I), C4(H00J), C10(H00K), C3(H00M)
3.c Idealised Me refined as rotating group:
 C18(H00C,H00D,H00E)
;
_shelx_res_checksum              80934
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.662