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_7156473
_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 H16 Br N O'
_chemical_formula_sum            'C18 H16 Br N O'
_chemical_formula_weight         342.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-21 deposited with the CCDC.
2018-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.399(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4795(3)
_cell_length_b                   11.3762(4)
_cell_length_c                   16.2210(5)
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8960
_cell_measurement_theta_min      6.5000
_cell_volume                     1563.38(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega   -4.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 28

  2 omega   28.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -30.0000 34

  3 omega  -47.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -63.0000 -180.0000 61

  4 omega   22.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   51.0646 26

  5 omega   -1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 76

  6 omega   33.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 90

  7 omega   35.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 46

  8 omega   50.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 26

  9 omega   35.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 64

 10 omega   68.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -150.0000 63

 11 omega   57.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 94

 12 omega   51.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 37

 13 omega   81.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -117.0000    3.0000 32

 14 omega   97.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -180.0000 81

 15 omega   52.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 27

 16 omega   62.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 27

 17 omega   38.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0204288000
_diffrn_orient_matrix_UB_12      -0.0986321000
_diffrn_orient_matrix_UB_13      -0.0637916000
_diffrn_orient_matrix_UB_21      0.0065541000
_diffrn_orient_matrix_UB_22      0.0925257000
_diffrn_orient_matrix_UB_23      -0.0691138000
_diffrn_orient_matrix_UB_31      0.1805285000
_diffrn_orient_matrix_UB_32      0.0077189000
_diffrn_orient_matrix_UB_33      0.0137373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5163
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.75
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0529P)^2^+0.6831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1183
_reflns_number_gt                2226
_reflns_number_total             2685
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob02094a2.cif
_cod_data_source_block           lilh_0426
_cod_depositor_comments
'Adding full bibliography for 7156470--7156473.cif.'
_cod_database_code               7156473
_reflns_odcompleteness_completeness 97.12
_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), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C13(H13), C2(H2), C17(H17), C3(H3), C14(H14), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_date_sample_data_collection 2018-04-28
_olex2_submission_special_instructions 'No special instructions were received'