Novel synthesis of fused spiro piperidone-cyclopropanes from cyclopropyl amides and electron-deficient alkenes.
Han, Xiao-Dan; Peng, Gao-Liang; Wang, Hui-Bin; Wu, Lei; Fu, Jian-Ping; Tang, Zhong-Sheng; Hu, Ju-Wu; Xiong, Wei; Organic & biomolecular chemistry 19 (2021) 3191–3198; doi:10.1039/d1ob00214g

data_7157924
_publ_section_title
;
 Novel synthesis of fused spiro piperidone-cyclopropanes from cyclopropyl
 amides and electron-deficient alkenes.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3191
_journal_page_last               3198
_journal_paper_doi               10.1039/d1ob00214g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-08-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-23 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.780(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.4303(7)
_cell_length_b                   23.1780(16)
_cell_length_c                   10.3616(8)
_cell_measurement_reflns_used    7126
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5780
_cell_measurement_theta_min      3.9590
_cell_volume                     2743.8(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -33.00  51.00   1.00    6.62    --  -15.92  57.00 -60.00   84
  2  \w    -20.00  56.00   1.00    6.62    --   17.01 -99.00 -90.00   76
  3  \w    -52.00  86.00   1.00    6.62    --   17.01   0.00 -60.00  138
  4  \w     35.00  89.00   1.00    6.62    --   17.01 178.00 -60.00   54
  5  \w    -83.00 -32.00   1.00    6.62    --  -15.92 -77.00   0.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0042327000
_diffrn_orient_matrix_UB_12      0.0116949000
_diffrn_orient_matrix_UB_13      -0.0629687000
_diffrn_orient_matrix_UB_21      -0.0170259000
_diffrn_orient_matrix_UB_22      0.0273741000
_diffrn_orient_matrix_UB_23      0.0234021000
_diffrn_orient_matrix_UB_31      0.0595641000
_diffrn_orient_matrix_UB_32      0.0070268000
_diffrn_orient_matrix_UB_33      0.0135174000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20404
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.52
_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  0.54670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         4833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0728
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+3.2371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2014
_refine_ls_wR_factor_ref         0.2095
_reflns_number_gt                3987
_reflns_number_total             4833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob00214g2.cif
_cod_data_source_block           yjj20180118
_cod_depositor_comments
'Adding full bibliography for 7157924--7157925.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7157924
_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 Secondary CH2 refined with riding coordinates:
 C7BA(H7BA,H7BB), C8CA(H8CA,H8CB)
2.b Aromatic/amide H refined with riding coordinates:
 C9BA(H9BA), C0CA(H0CA), C7CA(H7CA)
2.c Idealised Me refined as rotating group:
 C4CA(H4CA,H4CB,H4CC), C1DA(H1DA,H1DB,H1DC)
;
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.642