An environmentally benign double Michael addition reaction of heterocyclic ketene aminals with quinone monoketals for diastereoselective synthesis of highly functionly morphan derivatives in water
Ma, Yulu; Wang, Kai-Min; Huang, Rong; Lin, Jun; Yan, Sheng-Jiao; Green Chem.  (2017) –; doi:10.1039/C7GC01435J

data_7228528
_publ_section_title
;
 An environmentally benign double Michael addition reaction of
 heterocyclic ketene aminals with quinone monoketals for
 diastereoselective synthesis of highly functionly morphan derivatives in
 water
;
_journal_name_full               'Green Chem.'
_journal_paper_doi               10.1039/C7GC01435J
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H23 F N2 O4, 0.5(H2 O)'
_chemical_formula_sum            'C20 H24 F N2 O4.5'
_chemical_formula_weight         383.31
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-05-01 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.5910(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3686(8)
_cell_length_b                   15.9846(11)
_cell_length_c                   9.9812(7)
_cell_measurement_reflns_used    8904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.20
_cell_volume                     1808.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19064
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         1.27
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         9463
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.1693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                8786
_reflns_number_total             9463
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7gc01435j2.cif
_cod_data_source_block           mo_yd_lj_b3_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

2017-11-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P c'
_cod_original_formula_moiety     '2(C20 H23 F N2 O4), H2 O'
_cod_original_formula_sum        'C40 H48 F2 N4 O9'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     766.82
_cod_database_code               7228528