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_7156472
_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         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35
_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             2018-05-16
_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                 105.432(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2569(18)
_cell_length_b                   15.608(2)
_cell_length_c                   10.8924(18)
_cell_measurement_reflns_used    1125
_cell_measurement_temperature    232(6)
_cell_measurement_theta_max      27.2420
_cell_measurement_theta_min      4.0810
_cell_volume                     1517.0(5)
_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      232(6)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -50.00  -17.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273   77.0000   90.0000 22

  2 omega  -38.00   88.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  120.0000 84

  3 omega   20.00   87.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -30.0000 45
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0541763000
_diffrn_orient_matrix_UB_12      -0.0162699000
_diffrn_orient_matrix_UB_13      0.0538405000
_diffrn_orient_matrix_UB_21      -0.0581164000
_diffrn_orient_matrix_UB_22      -0.0144986000
_diffrn_orient_matrix_UB_23      0.0261457000
_diffrn_orient_matrix_UB_31      -0.0011442000
_diffrn_orient_matrix_UB_32      -0.0398759000
_diffrn_orient_matrix_UB_33      -0.0314135000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5621
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80876
_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    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0812
_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^)+(0.0712P)^2^+0.6736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2195
_reflns_number_gt                1790
_reflns_number_total             2987
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ob02094a2.cif
_cod_data_source_block           lilh_423_4
_cod_depositor_comments
'Adding full bibliography for 7156470--7156473.cif.'
_cod_original_cell_volume        1517.1(4)
_cod_database_code               7156472
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c 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)
2.d Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C12(H12A,H12B,H12C)
;
_olex2_date_sample_data_collection 2018-05-16
_olex2_submission_special_instructions 'No special instructions were received'