New Friedel-Crafts strategy for preparing 3-acylindoles.
Li, Lian-Hua; Niu, Zhi-Jie; Liang, Yong-Min; Organic & biomolecular chemistry 16 (2018) 7792–7796; doi:10.1039/c8ob02094a

data_7156471
_publ_section_title
;
 New Friedel-Crafts strategy for preparing 3-acylindoles.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7792
_journal_page_last               7796
_journal_paper_doi               10.1039/c8ob02094a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C18 H17 N O'
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_symmetry_space_group_name_Hall  '-I 2yc'
_symmetry_space_group_name_H-M   'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-25 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.711(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   22.0489(5)
_cell_length_b                   15.0516(3)
_cell_length_c                   18.1612(4)
_cell_measurement_reflns_used    4318
_cell_measurement_temperature    290.04(10)
_cell_measurement_theta_max      69.8630
_cell_measurement_theta_min      10.3330
_cell_volume                     5708.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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    -15.00  73.00   1.00    1.00    --   54.00 -57.00 120.00   88
  2  \w     50.00 104.00   1.00    1.00    --   54.00-125.00  90.00   54
  3  \w     64.00  90.00   1.00    1.00    --  108.00-111.00  90.00   26
  4  \w     40.00 125.00   1.00    1.00    --  108.00 -50.00   0.00   85
  5  \w     81.00 108.00   1.00    1.00    --  108.00-111.00 -60.00   27
  6  \w     38.00  97.00   1.00    1.00    --  108.00 -50.00  90.00   59
  7  \w     41.00 116.00   1.00    1.00    --   54.00  57.00  30.00   75
  8  \w    108.00 157.00   1.00    1.00    --  108.00 111.00 120.00   49
  9  \w    105.00 171.00   1.00    1.00    --  108.00 111.00  90.00   66
 10  \w    100.00 177.00   1.00    1.00    --  108.00 111.00 150.00   77
 11  \w     80.00 105.00   1.00    1.00    --  108.00 178.00 -60.00   25
 12  \w     97.00 132.00   1.00    1.00    --  108.00  63.00-180.00   35
 13  \w     86.00 169.00   1.00    1.00    --  108.00  50.00-120.00   83
 14  \w     68.00 122.00   1.00    1.00    --   54.00  57.00 -90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0633538000
_diffrn_orient_matrix_UB_12      0.0362810000
_diffrn_orient_matrix_UB_13      0.0067506000
_diffrn_orient_matrix_UB_21      0.0241495000
_diffrn_orient_matrix_UB_22      -0.0180923000
_diffrn_orient_matrix_UB_23      0.0881368000
_diffrn_orient_matrix_UB_31      0.0291196000
_diffrn_orient_matrix_UB_32      0.0939538000
_diffrn_orient_matrix_UB_33      0.0143786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10519
_diffrn_reflns_theta_full        69.96
_diffrn_reflns_theta_max         69.96
_diffrn_reflns_theta_min         10.28
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+1.6154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                4402
_reflns_number_total             5245
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob02094a2.cif
_cod_data_source_block           lilh_0306_4_2
_cod_depositor_comments
'Adding full bibliography for 7156470--7156473.cif.'
_cod_database_code               7156471
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C28(H28A,H28B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C31(H31),
  C32(H32), C33(H33), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C0AA(H0AA,H0AB,H0AC)
;
_olex2_date_sample_data_collection 2018-03-06
_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 3.442
_oxdiff_exptl_absorpt_empirical_full_min 0.696