Diastereo- and enantioselective construction of cyclohexanone-fused spirospyrazolones containing four consecutive stereocenters through asymmetric sequential reactions
Li, Jun-Hua; Cui, Zhi-Hao; Du, Da-Ming; Organic Chemistry Frontiers 3 (2016) 1087–; doi:10.1039/C6QO00208K

data_1553479
_publ_section_title
;
 Diastereo- and enantioselective construction of cyclohexanone-fused
 spirospyrazolones containing four consecutive stereocenters through
 asymmetric sequential reactions
;
_journal_issue                   9
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1087
_journal_paper_doi               10.1039/C6QO00208K
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H23 Cl N4 O7'
_chemical_formula_sum            'C28 H23 Cl N4 O7'
_chemical_formula_weight         562.95
_chemical_melting_point          479.5(15)
_chemical_name_systematic
(5R,8S,9R,10R)-2-(4-Chlorophenyl)-8-(2-methoxyphenyl)-4-methyl-9-nitro-10-(3-nitrophenyl)-2,3-diazaspiro[4.5]dec-3-ene-1,6-dione
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-25 deposited with the CCDC.
2016-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.766(3)
_cell_length_b                   16.240(3)
_cell_length_c                   13.427(3)
_cell_measurement_reflns_used    8428
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.2539
_cell_volume                     2648.0(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18000
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         11318
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0718
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1074P)^2^+1.6710P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.2157
_reflns_number_gt                10330
_reflns_number_total             11318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00208k2.cif
_cod_data_source_block           bl-15
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '478-481' was changed to
'479.5(15)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2648.0(9)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1553479
_solvent_exptl_crystal_recrystallization_method 'Ethyl acetate/Petroleum ether'