#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301865 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/85/7228530.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7228530
loop_
_publ_author_name
'Ma, Yulu'
'Wang, Kai-Min'
'Huang, Rong'
'Lin, Jun'
'Yan, Sheng-Jiao'
_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_sum            'C21 H26 N2 O4'
_chemical_formula_weight         370.44
_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                 108.6090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.6978(15)
_cell_length_b                   12.2595(12)
_cell_length_c                   21.830(2)
_cell_measurement_temperature    298(2)
_cell_volume                     3727.8(6)
_computing_cell_refinement       'Bruker apex II'
_computing_data_collection       'Bruker apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10383
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0057(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0426
_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/[σ²(Fo²)+(0.1000P)²+0.2933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                2476
_reflns_number_total             3342
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7gc01435j2.cif
_cod_data_source_block           1
_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        3727.9(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C42 H52 N4 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     740.88
_cod_database_code               7228530
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.19584(11) 1.04251(12) 0.24252(7) 0.0366(4) Uani 1 1 d .
N2 N 0.13452(12) 0.88520(14) 0.27364(7) 0.0441(4) Uani 1 1 d .
H2A H 0.1021 0.8260 0.2624 0.053 Uiso 1 1 calc R
O1 O 0.05656(11) 0.73952(11) 0.18741(6) 0.0520(4) Uani 1 1 d .
O2 O 0.29487(8) 0.97965(11) 0.15291(6) 0.0407(4) Uani 1 1 d .
O3 O 0.22851(9) 1.13198(10) 0.09103(6) 0.0375(3) Uani 1 1 d .
O4 O -0.04468(10) 1.15422(15) 0.14454(8) 0.0669(5) Uani 1 1 d .
C1 C 0.13976(15) 0.73976(16) 0.05716(9) 0.0447(5) Uani 1 1 d .
H1 H 0.1996 0.7696 0.0789 0.054 Uiso 1 1 calc R
C2 C 0.12613(18) 0.68382(18) -0.00041(10) 0.0576(6) Uani 1 1 d .
H2 H 0.1766 0.6761 -0.0171 0.069 Uiso 1 1 calc R
C3 C 0.0376(2) 0.63979(18) -0.03271(11) 0.0641(7) Uani 1 1 d .
H3 H 0.0281 0.6025 -0.0713 0.077 Uiso 1 1 calc R
C4 C -0.03614(18) 0.6509(2) -0.00814(11) 0.0628(7) Uani 1 1 d .
H4 H -0.0959 0.6213 -0.0302 0.075 Uiso 1 1 calc R
C5 C -0.02279(15) 0.70547(17) 0.04898(9) 0.0480(5) Uani 1 1 d .
H5 H -0.0736 0.7116 0.0655 0.058 Uiso 1 1 calc R
C6 C 0.06521(13) 0.75155(14) 0.08247(8) 0.0360(4) Uani 1 1 d .
C7 C 0.07892(13) 0.80202(15) 0.14788(8) 0.0358(4) Uani 1 1 d .
C8 C 0.11670(12) 0.90774(15) 0.16170(8) 0.0330(4) Uani 1 1 d .
C9 C 0.12634(12) 0.98329(14) 0.10898(8) 0.0327(4) Uani 1 1 d .
H9 H 0.1322 0.9391 0.0730 0.039 Uiso 1 1 calc R
C10 C 0.21712(12) 1.05273(14) 0.13573(8) 0.0329(4) Uani 1 1 d .
C11 C 0.20644(12) 1.11793(14) 0.19285(8) 0.0341(4) Uani 1 1 d .
H11 H 0.2655 1.1600 0.2117 0.041 Uiso 1 1 calc R
C12 C 0.12174(13) 1.19943(15) 0.16995(9) 0.0385(5) Uani 1 1 d .
H12 H 0.1360 1.2467 0.1380 0.046 Uiso 1 1 calc R
C13 C 0.03015(14) 1.13886(16) 0.13413(9) 0.0408(5) Uani 1 1 d .
C14 C 0.03816(13) 1.05940(16) 0.08363(9) 0.0395(5) Uani 1 1 d .
H14A H 0.0430 1.0996 0.0465 0.047 Uiso 1 1 calc R
H14B H -0.0197 1.0155 0.0695 0.047 Uiso 1 1 calc R
C15 C 0.14838(12) 0.94657(15) 0.22662(8) 0.0344(4) Uani 1 1 d .
C16 C 0.16983(17) 0.91087(18) 0.34196(9) 0.0536(6) Uani 1 1 d .
H16A H 0.1854 0.8441 0.3670 0.064 Uiso 1 1 calc R
H16B H 0.1207 0.9491 0.3544 0.064 Uiso 1 1 calc R
C17 C 0.25781(17) 0.98107(18) 0.35552(9) 0.0556(6) Uani 1 1 d .
H17A H 0.3103 0.9386 0.3499 0.067 Uiso 1 1 calc R
H17B H 0.2768 1.0065 0.3999 0.067 Uiso 1 1 calc R
C18 C 0.23773(16) 1.07730(17) 0.31038(9) 0.0478(5) Uani 1 1 d .
H18A H 0.1937 1.1265 0.3214 0.057 Uiso 1 1 calc R
H18B H 0.2970 1.1165 0.3155 0.057 Uiso 1 1 calc R
C19 C 0.11085(16) 1.27471(18) 0.22267(10) 0.0521(6) Uani 1 1 d .
H19A H 0.0660 1.3317 0.2034 0.078 Uiso 1 1 calc R
H19B H 0.1720 1.3062 0.2457 0.078 Uiso 1 1 calc R
H19C H 0.0877 1.2337 0.2521 0.078 Uiso 1 1 calc R
C20 C 0.38747(14) 1.02583(19) 0.18442(11) 0.0539(6) Uani 1 1 d .
H20A H 0.3976 1.0869 0.1599 0.081 Uiso 1 1 calc R
H20B H 0.4361 0.9719 0.1875 0.081 Uiso 1 1 calc R
H20C H 0.3909 1.0497 0.2270 0.081 Uiso 1 1 calc R
C21 C 0.23537(16) 1.08885(18) 0.03201(9) 0.0495(5) Uani 1 1 d .
H21A H 0.2847 1.0343 0.0413 0.074 Uiso 1 1 calc R
H21B H 0.2509 1.1465 0.0073 0.074 Uiso 1 1 calc R
H21C H 0.1751 1.0567 0.0077 0.074 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C15 N1 C11 121.60(14)
C15 N1 C18 121.62(15)
C11 N1 C18 116.78(15)
C15 N2 C16 125.08(17)
C15 N2 H2A 117.5
C16 N2 H2A 117.5
C10 O2 C20 116.33(15)
C10 O3 C21 115.08(14)
C6 C1 C2 120.61(19)
C6 C1 H1 119.7
C2 C1 H1 119.7
C3 C2 C1 119.8(2)
C3 C2 H2 120.1
C1 C2 H2 120.1
C4 C3 C2 120.0(2)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.4(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 121.1(2)
C4 C5 H5 119.5
C6 C5 H5 119.5
C1 C6 C5 118.12(18)
C1 C6 C7 122.49(17)
C5 C6 C7 119.09(17)
O1 C7 C8 125.42(16)
O1 C7 C6 114.15(15)
C8 C7 C6 120.38(15)
C7 C8 C15 120.21(16)
C7 C8 C9 121.75(15)
C15 C8 C9 118.04(15)
C8 C9 C10 109.29(13)
C8 C9 C14 111.62(14)
C10 C9 C14 109.21(14)
C8 C9 H9 108.9
C10 C9 H9 108.9
C14 C9 H9 108.9
O2 C10 O3 110.76(13)
O2 C10 C11 113.67(14)
O3 C10 C11 105.48(14)
O2 C10 C9 106.41(14)
O3 C10 C9 113.34(13)
C11 C10 C9 107.29(14)
N1 C11 C10 109.56(14)
N1 C11 C12 112.34(14)
C10 C11 C12 110.77(14)
N1 C11 H11 108.0
C10 C11 H11 108.0
C12 C11 H11 108.0
C13 C12 C19 113.33(16)
C13 C12 C11 109.87(15)
C19 C12 C11 114.48(15)
C13 C12 H12 106.2
C19 C12 H12 106.2
C11 C12 H12 106.2
O4 C13 C14 121.90(18)
O4 C13 C12 122.59(19)
C14 C13 C12 115.51(15)
C13 C14 C9 112.37(14)
C13 C14 H14A 109.1
C9 C14 H14A 109.1
C13 C14 H14B 109.1
C9 C14 H14B 109.1
H14A C14 H14B 107.9
N2 C15 N1 118.88(16)
N2 C15 C8 119.55(16)
N1 C15 C8 121.52(15)
N2 C16 C17 109.29(17)
N2 C16 H16A 109.8
C17 C16 H16A 109.8
N2 C16 H16B 109.8
C17 C16 H16B 109.8
H16A C16 H16B 108.3
C16 C17 C18 110.09(18)
C16 C17 H17A 109.6
C18 C17 H17A 109.6
C16 C17 H17B 109.6
C18 C17 H17B 109.6
H17A C17 H17B 108.2
N1 C18 C17 111.29(16)
N1 C18 H18A 109.4
C17 C18 H18A 109.4
N1 C18 H18B 109.4
C17 C18 H18B 109.4
H18A C18 H18B 108.0
C12 C19 H19A 109.5
C12 C19 H19B 109.5
H19A C19 H19B 109.5
C12 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
O2 C20 H20A 109.5
O2 C20 H20B 109.5
H20A C20 H20B 109.5
O2 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
O3 C21 H21A 109.5
O3 C21 H21B 109.5
H21A C21 H21B 109.5
O3 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C15 1.355(2)
N1 C11 1.471(2)
N1 C18 1.474(2)
N2 C15 1.340(2)
N2 C16 1.449(2)
N2 H2A 0.8600
O1 C7 1.273(2)
O2 C10 1.406(2)
O2 C20 1.431(2)
O3 C10 1.424(2)
O3 C21 1.426(2)
O4 C13 1.207(2)
C1 C6 1.383(3)
C1 C2 1.389(3)
C1 H1 0.9300
C2 C3 1.378(3)
C2 H2 0.9300
C3 C4 1.360(3)
C3 H3 0.9300
C4 C5 1.373(3)
C4 H4 0.9300
C5 C6 1.387(3)
C5 H5 0.9300
C6 C7 1.509(2)
C7 C8 1.404(3)
C8 C15 1.425(2)
C8 C9 1.519(2)
C9 C10 1.533(2)
C9 C14 1.549(2)
C9 H9 0.9800
C10 C11 1.531(2)
C11 C12 1.549(3)
C11 H11 0.9800
C12 C13 1.518(3)
C12 C19 1.523(3)
C12 H12 0.9800
C13 C14 1.504(3)
C14 H14A 0.9700
C14 H14B 0.9700
C16 C17 1.502(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.505(3)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 0.1(3)
C1 C2 C3 C4 -0.2(3)
C2 C3 C4 C5 -0.3(4)
C3 C4 C5 C6 0.8(3)
C2 C1 C6 C5 0.4(3)
C2 C1 C6 C7 173.96(17)
C4 C5 C6 C1 -0.8(3)
C4 C5 C6 C7 -174.65(19)
C1 C6 C7 O1 -121.05(19)
C5 C6 C7 O1 52.5(2)
C1 C6 C7 C8 56.8(3)
C5 C6 C7 C8 -129.71(19)
O1 C7 C8 C15 10.8(3)
C6 C7 C8 C15 -166.79(16)
O1 C7 C8 C9 -169.99(17)
C6 C7 C8 C9 12.5(3)
C7 C8 C9 C10 -144.96(17)
C15 C8 C9 C10 34.3(2)
C7 C8 C9 C14 94.1(2)
C15 C8 C9 C14 -86.61(19)
C20 O2 C10 O3 61.54(19)
C20 O2 C10 C11 -57.0(2)
C20 O2 C10 C9 -174.87(15)
C21 O3 C10 O2 59.39(19)
C21 O3 C10 C11 -177.21(15)
C21 O3 C10 C9 -60.12(19)
C8 C9 C10 O2 62.37(17)
C14 C9 C10 O2 -175.26(13)
C8 C9 C10 O3 -175.66(13)
C14 C9 C10 O3 -53.29(18)
C8 C9 C10 C11 -59.63(18)
C14 C9 C10 C11 62.74(17)
C15 N1 C11 C10 -34.8(2)
C18 N1 C11 C10 146.34(16)
C15 N1 C11 C12 88.78(19)
C18 N1 C11 C12 -90.10(19)
O2 C10 C11 N1 -57.51(18)
O3 C10 C11 N1 -179.04(13)
C9 C10 C11 N1 59.84(17)
O2 C10 C11 C12 178.01(14)
O3 C10 C11 C12 56.48(17)
C9 C10 C11 C12 -64.64(18)
N1 C11 C12 C13 -66.84(18)
C10 C11 C12 C13 56.05(18)
N1 C11 C12 C19 62.0(2)
C10 C11 C12 C19 -175.10(15)
C19 C12 C13 O4 3.8(3)
C11 C12 C13 O4 133.3(2)
C19 C12 C13 C14 -177.25(15)
C11 C12 C13 C14 -47.8(2)
O4 C13 C14 C9 -132.91(19)
C12 C13 C14 C9 48.2(2)
C8 C9 C14 C13 66.06(19)
C10 C9 C14 C13 -54.90(19)
C16 N2 C15 N1 -2.6(3)
C16 N2 C15 C8 174.81(18)
C11 N1 C15 N2 -174.83(16)
C18 N1 C15 N2 4.0(3)
C11 N1 C15 C8 7.8(3)
C18 N1 C15 C8 -173.34(17)
C7 C8 C15 N2 -5.6(3)
C9 C8 C15 N2 175.15(16)
C7 C8 C15 N1 171.74(16)
C9 C8 C15 N1 -7.5(3)
C15 N2 C16 C17 -26.3(3)
N2 C16 C17 C18 51.8(2)
C15 N1 C18 C17 23.8(3)
C11 N1 C18 C17 -157.30(18)
C16 C17 C18 N1 -51.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203624
