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_1546790
_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         'C25 H20 N2 O3'
_chemical_formula_sum            'C25 H20 N2 O3'
_chemical_formula_weight         396.43
_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
_audit_creation_date             2016-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.220(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9800(3)
_cell_length_b                   10.4842(3)
_cell_length_c                   19.3010(6)
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3980
_cell_measurement_theta_min      4.6060
_cell_volume                     1965.99(10)
_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)'
_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 0.9989
_diffrn_measured_fraction_theta_max 0.9660
_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    -57.00 -22.00   1.00    1.00    --  -40.98 -37.00   0.00   35
  2  \w    -35.00  73.00   1.00    1.00    --   40.98 -77.00 -30.00  108
  3  \w     64.00 110.00   1.00    1.00    --  106.95-125.00  30.00   46
  4  \w     49.00 114.00   1.00    1.00    --  106.95-125.00 150.00   65
  5  \w     88.00 114.00   1.00    1.00    --  106.95  30.00 120.00   26
  6  \w    129.00 175.00   1.00    1.00    --  106.95  30.00 120.00   46
  7  \w     95.00 174.00   1.00    1.00    --  106.95 125.00  30.00   79
  8  \w    143.00 178.00   1.00    1.00    --  106.95  45.00-150.00   35
  9  \w     92.00 130.00   1.00    1.00    --  106.95  45.00-180.00   38
 10  \w     43.00 135.00   1.00    1.00    --  106.95 -30.00 -90.00   92
 11  \w    -64.00   7.00   1.00    1.00    --  -40.98  37.00-180.00   71
 12  \w   -109.00 -74.00   1.00    1.00    --  -40.98 -37.00   0.00   35
;
_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      0.0025179000
_diffrn_orient_matrix_UB_12      0.1443542000
_diffrn_orient_matrix_UB_13      0.0152700000
_diffrn_orient_matrix_UB_21      -0.1581244000
_diffrn_orient_matrix_UB_22      0.0045651000
_diffrn_orient_matrix_UB_23      -0.0244193000
_diffrn_orient_matrix_UB_31      -0.0118025000
_diffrn_orient_matrix_UB_32      -0.0274867000
_diffrn_orient_matrix_UB_33      0.0767448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7660
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.710
_diffrn_reflns_theta_min         4.621
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76761
_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            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0546P)^2^+0.5194P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3470
_reflns_number_total             3848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02121_si_004.cif
_cod_data_source_block           exp_150
_cod_depositor_comments          'Adding full bibliography for 1546790.cif.'
_cod_original_cell_volume        1965.99(11)
_cod_database_code               1546790
_shelx_estimated_absorpt_t_max   0.870
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.89
_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 Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C23(H23), C6(H6), C12(H12), C14(H14), C9(H9), C15(H15), C8(H8),
 C7(H7), C17(H17), C16(H16), C22(H22), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_shelxl_version_number     2014/7
_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 1.451
_oxdiff_exptl_absorpt_empirical_full_min 0.692