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_7228529
_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_formula_moiety         'C21 H25 Cl N2 O4, 1.5(H2 O)'
_chemical_formula_sum            'C21 H28 Cl N2 O5.5'
_chemical_formula_weight         431.90
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.558(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.064(2)
_cell_length_b                   9.1067(9)
_cell_length_c                   19.757(2)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.41
_cell_volume                     4050.4(7)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18766
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9143
_exptl_absorpt_correction_T_min  0.8475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.707
_refine_diff_density_min         -1.290
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4882
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0902P)^2^+7.7654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1596
_reflns_number_gt                4403
_reflns_number_total             4882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7gc01435j2.cif
_cod_data_source_block           mo_yd_lj2_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 

2018-03-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4050.5(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_moiety     '2(C21 H25 Cl N2 O4), 3(H2 O)'
_cod_original_formula_sum        'C42 H56 Cl2 N4 O11'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     863.81
_cod_database_code               7228529