CuCl/Et3N-Catalyzed Synthesis of Indanone-Fused 2-Methylene Pyrrolidines from Enynals and Propargylamines.
Qiu, Shaotong; Chen, Lianfen; Jiang, Huanfeng; Zhu, Shifa; Organic letters 19 (2017) 4540–4543; doi:10.1021/acs.orglett.7b02121

data_1547017
_publ_section_title
;
 CuCl/Et3N-Catalyzed Synthesis of Indanone-Fused 2-Methylene Pyrrolidines
 from Enynals and Propargylamines.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4540
_journal_page_last               4543
_journal_paper_doi               10.1021/acs.orglett.7b02121
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 109.769(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   14.4270(4)
_cell_length_b                   6.42046(13)
_cell_length_c                   17.0456(5)
_cell_measurement_reflns_used    5675
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3550
_cell_measurement_theta_min      5.3580
_cell_volume                     1485.85(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    -63.00  30.00   1.00    1.00    --  -40.98  37.00 -60.00   93
  2  \w     15.00  71.00   1.00    1.00    --   40.98 -99.00 -30.00   56
  3  \w     88.00 123.00   1.00    1.00    --   40.98-169.00 -72.00   35
  4  \w     65.00 108.00   1.00    1.33    --  106.95 -94.00 -30.00   43
  5  \w     38.00 105.00   1.00    1.33    --  106.95 -94.00 -90.00   67
  6  \w     74.00 104.00   1.00    1.33    --  106.95 -94.00-180.00   30
  7  \w     39.00 132.00   1.00    1.33    --  106.95 -45.00 -60.00   93
  8  \w    106.00 177.00   1.00    1.33    --  106.95  30.00-120.00   71
  9  \w    139.00 178.00   1.00    1.33    --  106.95  61.00 -90.00   39
 10  \w    147.00 178.00   1.00    1.33    --  106.95 125.00-180.00   31
 11  \w     79.00 115.00   1.00    1.33    --  106.95  61.00 -90.00   36
 12  \w     61.00 178.00   1.00    1.33    --  106.95  15.00   0.00  117
 13  \w    115.00 142.00   1.00    1.33    --  106.95 115.00 160.00   27
 14  \w     35.00 125.00   1.00    1.33    --  106.95 -45.00 120.00   90
 15  \w     31.00  58.00   1.00    1.33    --  106.95 -94.00 -30.00   27
 16  \w     24.00 105.00   1.00    1.33    --  106.95 -94.00 120.00   81
 17  \w   -111.00 -17.00   1.00    1.00    --  -40.98 -37.00 120.00   94
 18  \w   -106.00 -30.00   1.00    1.00    --  -40.98 -57.00  30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0789883000
_diffrn_orient_matrix_UB_12      0.0301854000
_diffrn_orient_matrix_UB_13      -0.0412983000
_diffrn_orient_matrix_UB_21      0.0814607000
_diffrn_orient_matrix_UB_22      -0.0291971000
_diffrn_orient_matrix_UB_23      0.0852445000
_diffrn_orient_matrix_UB_31      -0.0000628000
_diffrn_orient_matrix_UB_32      -0.2362189000
_diffrn_orient_matrix_UB_33      -0.0158618000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9353
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.666
_diffrn_reflns_theta_min         5.374
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0518P)^2^+0.5652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2715
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02121_si_005.cif
_cod_data_source_block           exp_218
_cod_original_cell_volume        1485.85(6)
_cod_database_code               1547017
_shelx_shelxl_version_number     2014/7
_cell_oxdiff_angle_alpha         90.014(2)
_cell_oxdiff_angle_beta          109.753(3)
_cell_oxdiff_angle_gamma         90.036(2)
_cell_oxdiff_length_a            14.4259(5)
_cell_oxdiff_length_b            6.42107(17)
_cell_oxdiff_length_c            17.0436(6)
_cell_oxdiff_measurement_reflns_used 5675
_cell_oxdiff_volume              1485.85(8)
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 99.93
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C16(H16), C12(H12), C5(H5), C13(H13), C15(H15), C4(H4),
 C14(H14)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.589