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_7159937
_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         'C20 H16 Cl2 N2 O6'
_chemical_formula_sum            'C20 H16 Cl2 N2 O6'
_chemical_formula_weight         451.25
_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             2022-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                95.590(2)
_cell_angle_beta                 98.647(2)
_cell_angle_gamma                114.340(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0746(2)
_cell_length_b                   8.2867(3)
_cell_length_c                   16.9277(3)
_cell_measurement_reflns_used    14652
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8580
_cell_measurement_theta_min      2.4620
_cell_volume                     1004.16(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -17.00 100.00   0.50    3.10    --   10.60  82.00 -30.00  234
  2  \w    -17.00 100.00   0.50    3.10    --   10.60  82.00   0.00  234
  3  \w    -17.00 100.00   0.50    3.10    --   10.60  82.00-150.00  234
  4  \w    -79.00  36.00   0.50    3.10    --   10.60 -77.00 150.00  230
  5  \w    -17.00 100.00   0.50    3.10    --   10.60  82.00-180.00  234
  6  \w    -17.00 100.00   0.50    3.10    --   10.60  82.00-120.00  234
  7  \w   -100.00  17.00   0.50    3.10    --  -10.90 -82.00 -30.00  234
  8  \w    -41.00  79.00   0.50    3.10    --  -10.90  57.00  60.00  240
  9  \w   -100.00  15.00   0.50    3.10    --  -10.90 -77.00  30.00  230
 10  \w    -48.00  79.00   0.50    3.10    --  -10.90  37.00 -90.00  254
 11  \w    -38.00  79.00   0.50    3.10    --  -10.90  82.00  60.00  234
 12  \w    -36.00  79.00   0.50    3.10    --  -10.90  77.00 120.00  230
 13  \w    -38.00   6.00   0.50    3.10    --  -10.90  82.00-150.00   88
 14  \w    -38.00  79.00   0.50    3.10    --  -10.90  82.00 -60.00  234
;
_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      0.0198737000
_diffrn_orient_matrix_UB_12      0.0025064000
_diffrn_orient_matrix_UB_13      0.0424883000
_diffrn_orient_matrix_UB_21      -0.0398742000
_diffrn_orient_matrix_UB_22      0.0609081000
_diffrn_orient_matrix_UB_23      0.0061671000
_diffrn_orient_matrix_UB_31      -0.0879753000
_diffrn_orient_matrix_UB_32      -0.0734491000
_diffrn_orient_matrix_UB_33      -0.0033379000
_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  0.0369
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25407
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.473
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49890
_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    1.492
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0397
_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^)+(0.0486P)^2^+0.8160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3037
_reflns_number_total             3539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00488d3.cif
_cod_data_source_block           k11111-myc-h(chq3739)_auto
_cod_depositor_comments
'Adding full bibliography for 7159934--7159937.cif.'
_cod_original_cell_volume        1004.16(5)
_cod_database_code               7159937
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.839
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O2, N2
 with sigma for 1-2 distances of 0.0002 and sigma for 1-3 distances of 0.0001
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C2(H2), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              57103
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.629