Directed C-C Bond Cleavage of Cyclopropane Intermediate Generated from N-Tosylhydrazones and Stable Enaminones: Expedient Synthesis of Functionalized 1, 4–Ketoaldehydes
Ni, Meiyan; Zhang, Jianguo; Liang, Xiaoyu; Jiang, Yaojia; Loh, Teck Peng; Chem. Commun.  (2017) –; doi:10.1039/C7CC07178G

data_7120828
_publ_section_title
;
 Directed C-C Bond Cleavage of Cyclopropane Intermediate Generated from
 N-Tosylhydrazones and Stable Enaminones: Expedient Synthesis of
 Functionalized 1, 4--Ketoaldehydes
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC07178G
_journal_year                    2017
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_weight         297.30
_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_update_record
;
2016-12-13 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.228(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3645(5)
_cell_length_b                   14.4689(12)
_cell_length_c                   15.7267(12)
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.98
_cell_volume                     1429.5(2)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2016)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2016)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Bruker AXS Inc., 2016)'
_diffrn_ambient_temperature      173.(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9259
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         2602
_refine_ls_number_restraints     531
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0554P)^2^+1.1173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                1666
_reflns_number_total             2602
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc07178g2.cif
_cod_data_source_block           yaojia2
_cod_database_code               7120828
_shelx_res_checksum              59157