Regioselective Synthesis of Acylated N-Heterocycles via the Cascade Reactions of Saturated Cyclic Amines with 2-Oxo-2-arylacetic Acids.
Shi, Xiaonan; Chen, Xi; Wang, Muhua; Zhang, Xinying; Fan, Xuesen; The Journal of organic chemistry 83 (2018) 6524–6533; doi:10.1021/acs.joc.8b00805

data_4035817
_publ_section_title
;
 Regioselective Synthesis of Acylated N-Heterocycles via the Cascade
 Reactions of Saturated Cyclic Amines with 2-Oxo-2-arylacetic Acids.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6524
_journal_page_last               6533
_journal_paper_doi               10.1021/acs.joc.8b00805
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C18 H17 N O'
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-31
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.2044(12)
_cell_length_b                   8.5077(7)
_cell_length_c                   7.4456(6)
_cell_measurement_reflns_used    3808
_cell_measurement_temperature    298.00(10)
_cell_measurement_theta_max      25.9630
_cell_measurement_theta_min      4.3670
_cell_volume                     1406.54(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     35.00  88.00   1.00    5.18    --   15.98 178.00  30.00   53
  2  \w     -1.00  83.00   1.00    5.18    --   15.98  57.00 150.00   84
  3  \w    -53.00  35.00   1.00    5.18    --   15.98 -38.00 150.00   88
  4  \w     34.00  77.00   1.00    5.18    --   15.98-178.00 150.00   43
  5  \w     -1.00  83.00   1.00    5.18    --   15.98  57.00 -60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0783597000
_diffrn_orient_matrix_UB_12      0.0085258000
_diffrn_orient_matrix_UB_13      -0.0204288000
_diffrn_orient_matrix_UB_21      -0.0259533000
_diffrn_orient_matrix_UB_22      -0.0296117000
_diffrn_orient_matrix_UB_23      0.0196986000
_diffrn_orient_matrix_UB_31      -0.0119133000
_diffrn_orient_matrix_UB_32      0.0083502000
_diffrn_orient_matrix_UB_33      0.0909599000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8719
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.649
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
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    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 881 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0536P)^2^+0.0968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0999
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                2256
_reflns_number_total             2409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00805_si_002.cif
_cod_data_source_block           3a
_cod_database_code               4035817
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 99.47
_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
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_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 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.461