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_7157925
_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         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-07-03
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2387(4)
_cell_length_b                   10.3818(4)
_cell_length_c                   9.6545(3)
_cell_measurement_reflns_used    1603
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.2740
_cell_measurement_theta_min      5.1600
_cell_volume                     1527.39(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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    -59.00  -1.00   1.00    8.00    --  -40.08  19.00 -60.00   58
  2  \w   -104.00 -16.00   1.00    8.00    --  -40.08 -38.00 120.00   88
  3  \w     59.00 178.00   1.00   22.00    --  105.81  15.00-180.00  119
  4  \w    111.00 173.00   1.00   22.00    --  105.81 125.00 -30.00   62
  5  \w     40.00  97.00   1.00   22.00    --  105.81-125.00-180.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1293123000
_diffrn_orient_matrix_UB_12      0.0692734000
_diffrn_orient_matrix_UB_13      -0.0357390000
_diffrn_orient_matrix_UB_21      -0.0690651000
_diffrn_orient_matrix_UB_22      -0.1313062000
_diffrn_orient_matrix_UB_23      -0.0177268000
_diffrn_orient_matrix_UB_31      -0.0628782000
_diffrn_orient_matrix_UB_32      0.0017288000
_diffrn_orient_matrix_UB_33      0.0928698000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3092
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.583
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         5.424
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1426
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0692
_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^)+(0.0480P)^2^+2.1307P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1315
_reflns_number_total             1426
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00214g2.cif
_cod_data_source_block           111
_cod_depositor_comments
'Adding full bibliography for 7157924--7157925.cif.'
_cod_database_code               7157925
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     C4A-C5-MGCL2
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.871
_reflns_odcompleteness_completeness 99.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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. Restrained distances
 C7-C12
 2.3 with sigma of 0.02
3. Others
 Fixed Sof: H6A(0.5) H6B(0.5) C8(0.5) C9(0.5) C10(0.5) H10B(0.5) H10A(0.5)
 C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C13(0.5)
 H13(0.5) H14A(0.5) H14B(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16(0.5) O4(0.5)
 O2(0.5) H2A(0.5) O3(0.5)
4.a Riding coordinates:
 C6(H6A,H6B), C10(H10B,H10A), C11(H11A,H11B), C12(H12A,H12B,H12C), C13(H13),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16), O2(H2A)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
;
_shelx_res_checksum              19467
_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 1.752
_oxdiff_exptl_absorpt_empirical_full_min 0.794