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_1547018
_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         'C20 H19 N O3'
_chemical_formula_sum            'C20 H19 N O3'
_chemical_formula_weight         321.36
_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'
_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                 105.694(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   11.7424(6)
_cell_length_b                   8.2014(4)
_cell_length_c                   17.3455(8)
_cell_measurement_reflns_used    3635
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4010
_cell_measurement_theta_min      4.0800
_cell_volume                     1608.17(14)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_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    -79.00  35.00   1.00    1.00    --  -40.98  19.00   0.00  114
  2  \w     48.00  79.00   1.00    1.00    --   40.98-125.00-180.00   31
  3  \w     39.00 107.00   1.00    1.44    --  106.95 -94.00-120.00   68
  4  \w     96.00 132.00   1.00    1.44    --  106.95 -45.00 -30.00   36
  5  \w     85.00 163.00   1.00    1.44    --  106.95  30.00  60.00   78
  6  \w     79.00 170.00   1.00    1.44    --  106.95  30.00 150.00   91
  7  \w     42.00 108.00   1.00    1.44    --  106.95 -94.00 -30.00   66
  8  \w     37.00  92.00   1.00    1.44    --  106.95 -45.00 -30.00   55
  9  \w    132.00 157.00   1.00    1.44    --  106.95 125.00-120.00   25
 10  \w   -113.00 -42.00   1.00    1.00    --  -40.98 -37.00-180.00   71
;
_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      0.0212800000
_diffrn_orient_matrix_UB_12      -0.0379027000
_diffrn_orient_matrix_UB_13      -0.0819668000
_diffrn_orient_matrix_UB_21      -0.1343392000
_diffrn_orient_matrix_UB_22      -0.0180418000
_diffrn_orient_matrix_UB_23      -0.0369608000
_diffrn_orient_matrix_UB_31      -0.0089485000
_diffrn_orient_matrix_UB_32      0.1830670000
_diffrn_orient_matrix_UB_33      -0.0206485000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5819
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.536
_diffrn_reflns_theta_min         4.087
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82550
_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    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0700
_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^)+(0.0251P)^2^+10.2243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.1997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2902
_reflns_number_total             3138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02121_si_006.cif
_cod_data_source_block           l10_2
_cod_original_cell_volume        1608.16(13)
_cod_database_code               1547018
_shelx_shelxl_version_number     2014/7
_cell_oxdiff_angle_alpha         89.991(4)
_cell_oxdiff_angle_beta          105.714(4)
_cell_oxdiff_angle_gamma         89.957(4)
_cell_oxdiff_length_a            11.7409(7)
_cell_oxdiff_length_b            8.2024(4)
_cell_oxdiff_length_c            17.3473(7)
_cell_oxdiff_measurement_reflns_used 3635
_cell_oxdiff_volume              1608.16(14)
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.824
_reflns_odcompleteness_completeness 99.87
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C15(H15), C6(H6), C16(H16), C14(H14), C5(H5), C3(H3A), C13(H13),
 C4(H4)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 1.269
_oxdiff_exptl_absorpt_empirical_full_min 0.598