#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301865 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/85/7228529.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_7228529
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_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       'φ and ω 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/[σ²(Fo²)+(0.0902P)²+7.7654P] where P=(Fo²+2Fc²)/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
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
Cl1 Cl 0.14206(2) 0.83196(5) 0.42372(3) 0.02564(15) Uani 1 1 d .
O1S O 0.09458(8) 0.2216(3) 0.31915(15) 0.0611(7) Uani 1 1 d D
H1SB H 0.0879(18) 0.260(5) 0.3547(14) 0.092 Uiso 1 1 d D
H1SA H 0.1294(8) 0.195(5) 0.332(2) 0.092 Uiso 1 1 d D
O4 O 0.43691(7) 0.14324(18) 0.55584(8) 0.0299(3) Uani 1 1 d .
O2S O 0.0000 0.3487(8) 0.2500 0.142(2) Uani 1 2 d S
H2SA H 0.0301 0.3085 0.2720 0.213 Uiso 1 1 d R
O2 O 0.38382(6) 0.33731(14) 0.29251(7) 0.0189(3) Uani 1 1 d .
O3 O 0.44502(6) 0.46501(14) 0.38411(7) 0.0199(3) Uani 1 1 d .
O1 O 0.21489(6) 0.15526(16) 0.35978(9) 0.0268(3) Uani 1 1 d .
N1 N 0.39721(7) 0.07061(16) 0.37423(8) 0.0170(3) Uani 1 1 d .
N2 N 0.30103(7) -0.02367(17) 0.35784(8) 0.0186(3) Uani 1 1 d .
C3 C 0.17599(8) 0.6658(2) 0.41067(10) 0.0181(4) Uani 1 1 d .
C2 C 0.20915(8) 0.5921(2) 0.46777(9) 0.0191(4) Uani 1 1 d .
H2 H 0.2131 0.6310 0.5132 0.023 Uiso 1 1 calc R
C1 C 0.23652(8) 0.4603(2) 0.45723(9) 0.0185(4) Uani 1 1 d .
H1 H 0.2592 0.4087 0.4959 0.022 Uiso 1 1 calc R
C6 C 0.23109(7) 0.4033(2) 0.39078(9) 0.0167(3) Uani 1 1 d .
C7 C 0.25499(8) 0.2537(2) 0.37818(9) 0.0173(3) Uani 1 1 d .
C8 C 0.31589(7) 0.23100(19) 0.38645(9) 0.0153(3) Uani 1 1 d .
C9 C 0.36094(7) 0.35105(19) 0.40835(9) 0.0152(3) Uani 1 1 d .
H9 H 0.3402 0.4477 0.3987 0.018 Uiso 1 1 calc R
C14 C 0.39165(8) 0.3461(2) 0.48637(9) 0.0182(4) Uani 1 1 d .
H14A H 0.4131 0.4397 0.4992 0.022 Uiso 1 1 calc R
H14B H 0.3608 0.3377 0.5140 0.022 Uiso 1 1 calc R
C13 C 0.43485(8) 0.2207(2) 0.50494(10) 0.0196(4) Uani 1 1 d .
C5 C 0.19739(8) 0.4805(2) 0.33458(10) 0.0206(4) Uani 1 1 d .
H5 H 0.1933 0.4420 0.2891 0.025 Uiso 1 1 calc R
C4 C 0.16982(8) 0.6125(2) 0.34391(10) 0.0208(4) Uani 1 1 d .
H4 H 0.1473 0.6647 0.3054 0.025 Uiso 1 1 calc R
C15 C 0.33862(8) 0.09006(19) 0.37253(9) 0.0158(3) Uani 1 1 d .
C11 C 0.44169(8) 0.19321(19) 0.38079(9) 0.0162(3) Uani 1 1 d .
C10 C 0.40792(8) 0.34071(19) 0.36400(9) 0.0158(3) Uani 1 1 d .
C20 C 0.34447(9) 0.4551(2) 0.26528(10) 0.0229(4) Uani 1 1 d .
H20A H 0.3073 0.4446 0.2812 0.034 Uiso 1 1 calc R
H20B H 0.3360 0.4522 0.2145 0.034 Uiso 1 1 calc R
H20C H 0.3632 0.5490 0.2815 0.034 Uiso 1 1 calc R
C12 C 0.47680(8) 0.1979(2) 0.45663(9) 0.0187(4) Uani 1 1 d .
H12A H 0.4987 0.1046 0.4683 0.022 Uiso 1 1 calc R
H12B H 0.5061 0.2790 0.4625 0.022 Uiso 1 1 calc R
C21 C 0.48310(9) 0.5159(2) 0.34032(12) 0.0278(4) Uani 1 1 d .
H21A H 0.5235 0.4792 0.3581 0.042 Uiso 1 1 calc R
H21B H 0.4835 0.6235 0.3400 0.042 Uiso 1 1 calc R
H21C H 0.4683 0.4796 0.2930 0.042 Uiso 1 1 calc R
C19 C 0.48347(8) 0.1630(2) 0.33184(10) 0.0206(4) Uani 1 1 d .
H19A H 0.5055 0.0719 0.3458 0.031 Uiso 1 1 calc R
H19B H 0.5115 0.2447 0.3342 0.031 Uiso 1 1 calc R
H19C H 0.4602 0.1531 0.2843 0.031 Uiso 1 1 calc R
C18 C 0.41992(8) -0.0795(2) 0.36761(11) 0.0210(4) Uani 1 1 d .
H18A H 0.4616 -0.0864 0.3937 0.025 Uiso 1 1 calc R
H18B H 0.4190 -0.1007 0.3182 0.025 Uiso 1 1 calc R
C17 C 0.38231(8) -0.1920(2) 0.39547(10) 0.0211(4) Uani 1 1 d .
H17A H 0.3971 -0.2923 0.3899 0.025 Uiso 1 1 calc R
H17B H 0.3845 -0.1746 0.4454 0.025 Uiso 1 1 calc R
C16 C 0.31865(8) -0.17692(19) 0.35510(10) 0.0193(4) Uani 1 1 d .
H16A H 0.3156 -0.2074 0.3064 0.023 Uiso 1 1 calc R
H16B H 0.2922 -0.2405 0.3757 0.023 Uiso 1 1 calc R
H1A H 0.2670(13) -0.004(3) 0.3574(14) 0.028(7) Uiso 1 1 d .
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'
Cl Cl 0.1484 0.1585 '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
H1SB O1S H1SA 102(2)
C10 O2 C20 116.25(14)
C10 O3 C21 119.84(15)
C15 N1 C18 119.24(15)
C15 N1 C11 124.27(14)
C18 N1 C11 116.48(14)
C15 N2 C16 125.10(16)
C15 N2 H1A 114(2)
C16 N2 H1A 120(2)
C4 C3 C2 121.91(17)
C4 C3 Cl1 119.20(14)
C2 C3 Cl1 118.88(14)
C3 C2 C1 118.81(17)
C3 C2 H2 120.6
C1 C2 H2 120.6
C6 C1 C2 120.78(17)
C6 C1 H1 119.6
C2 C1 H1 119.6
C1 C6 C5 118.78(16)
C1 C6 C7 122.06(16)
C5 C6 C7 118.85(16)
O1 C7 C8 125.17(17)
O1 C7 C6 114.23(15)
C8 C7 C6 120.61(16)
C7 C8 C15 120.71(16)
C7 C8 C9 122.75(16)
C15 C8 C9 116.52(15)
C8 C9 C10 108.64(14)
C8 C9 C14 113.71(14)
C10 C9 C14 109.80(14)
C8 C9 H9 108.2
C10 C9 H9 108.2
C14 C9 H9 108.2
C13 C14 C9 113.50(14)
C13 C14 H14A 108.9
C9 C14 H14A 108.9
C13 C14 H14B 108.9
C9 C14 H14B 108.9
H14A C14 H14B 107.7
O4 C13 C14 122.92(17)
O4 C13 C12 121.63(17)
C14 C13 C12 115.44(16)
C4 C5 C6 121.38(17)
C4 C5 H5 119.3
C6 C5 H5 119.3
C3 C4 C5 118.33(17)
C3 C4 H4 120.8
C5 C4 H4 120.8
N2 C15 N1 119.88(16)
N2 C15 C8 119.09(16)
N1 C15 C8 121.03(16)
N1 C11 C19 108.89(14)
N1 C11 C12 108.00(14)
C19 C11 C12 110.45(14)
N1 C11 C10 108.85(13)
C19 C11 C10 112.08(14)
C12 C11 C10 108.48(14)
O2 C10 O3 112.45(14)
O2 C10 C9 113.68(14)
O3 C10 C9 104.35(14)
O2 C10 C11 105.49(14)
O3 C10 C11 112.67(14)
C9 C10 C11 108.32(14)
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
C13 C12 C11 110.13(14)
C13 C12 H12A 109.6
C11 C12 H12A 109.6
C13 C12 H12B 109.6
C11 C12 H12B 109.6
H12A C12 H12B 108.1
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
C11 C19 H19A 109.5
C11 C19 H19B 109.5
H19A C19 H19B 109.5
C11 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
N1 C18 C17 110.46(14)
N1 C18 H18A 109.6
C17 C18 H18A 109.6
N1 C18 H18B 109.6
C17 C18 H18B 109.6
H18A C18 H18B 108.1
C16 C17 C18 108.16(15)
C16 C17 H17A 110.1
C18 C17 H17A 110.1
C16 C17 H17B 110.1
C18 C17 H17B 110.1
H17A C17 H17B 108.4
N2 C16 C17 108.25(15)
N2 C16 H16A 110.0
C17 C16 H16A 110.0
N2 C16 H16B 110.0
C17 C16 H16B 110.0
H16A C16 H16B 108.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7483(18)
O1S H1SB 0.827(10)
O1S H1SA 0.824(10)
O4 C13 1.221(2)
O2S H2SA 0.8205
O2 C10 1.401(2)
O2 C20 1.432(2)
O3 C10 1.423(2)
O3 C21 1.437(2)
O1 C7 1.283(2)
N1 C15 1.356(2)
N1 C18 1.480(2)
N1 C11 1.503(2)
N2 C15 1.341(2)
N2 C16 1.458(2)
N2 H1A 0.80(3)
C3 C4 1.384(3)
C3 C2 1.390(3)
C2 C1 1.393(3)
C2 H2 0.9500
C1 C6 1.392(2)
C1 H1 0.9500
C6 C5 1.399(3)
C6 C7 1.510(2)
C7 C8 1.394(2)
C8 C15 1.435(2)
C8 C9 1.506(2)
C9 C10 1.537(2)
C9 C14 1.551(2)
C9 H9 1.0000
C14 C13 1.508(2)
C14 H14A 0.9900
C14 H14B 0.9900
C13 C12 1.514(2)
C5 C4 1.390(3)
C5 H5 0.9500
C4 H4 0.9500
C11 C19 1.531(2)
C11 C12 1.541(3)
C11 C10 1.552(2)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C12 H12A 0.9900
C12 H12B 0.9900
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C18 C17 1.521(3)
C18 H18A 0.9900
C18 H18B 0.9900
C17 C16 1.517(3)
C17 H17A 0.9900
C17 H17B 0.9900
C16 H16A 0.9900
C16 H16B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1A O1 0.80(3) 1.89(3) 2.576(2) 143(3) .
O2S H2SA O1S 0.82 1.76 2.582(4) 179.8 .
O1S H1SA O1 0.824(10) 1.962(12) 2.782(2) 173(5) .
O1S H1SB O4 0.827(10) 2.162(11) 2.987(3) 175(4) 7_556
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
C4 C3 C2 C1 -0.5(3)
Cl1 C3 C2 C1 -179.53(14)
C3 C2 C1 C6 0.3(3)
C2 C1 C6 C5 -0.2(3)
C2 C1 C6 C7 -173.80(16)
C1 C6 C7 O1 106.7(2)
C5 C6 C7 O1 -66.9(2)
C1 C6 C7 C8 -73.5(2)
C5 C6 C7 C8 113.0(2)
O1 C7 C8 C15 1.7(3)
C6 C7 C8 C15 -178.14(15)
O1 C7 C8 C9 -179.87(17)
C6 C7 C8 C9 0.3(3)
C7 C8 C9 C10 -137.38(17)
C15 C8 C9 C10 41.1(2)
C7 C8 C9 C14 100.04(19)
C15 C8 C9 C14 -81.45(19)
C8 C9 C14 C13 71.81(19)
C10 C9 C14 C13 -50.1(2)
C9 C14 C13 O4 -135.2(2)
C9 C14 C13 C12 45.8(2)
C1 C6 C5 C4 0.4(3)
C7 C6 C5 C4 174.17(17)
C2 C3 C4 C5 0.6(3)
Cl1 C3 C4 C5 179.68(14)
C6 C5 C4 C3 -0.6(3)
C16 N2 C15 N1 11.6(3)
C16 N2 C15 C8 -168.20(16)
C18 N1 C15 N2 -6.8(2)
C11 N1 C15 N2 171.62(16)
C18 N1 C15 C8 172.99(16)
C11 N1 C15 C8 -8.6(3)
C7 C8 C15 N2 -6.4(3)
C9 C8 C15 N2 175.11(15)
C7 C8 C15 N1 173.84(16)
C9 C8 C15 N1 -4.7(2)
C15 N1 C11 C19 -138.55(17)
C18 N1 C11 C19 39.9(2)
C15 N1 C11 C12 101.49(18)
C18 N1 C11 C12 -80.03(18)
C15 N1 C11 C10 -16.1(2)
C18 N1 C11 C10 162.38(15)
C20 O2 C10 O3 -63.77(19)
C20 O2 C10 C9 54.5(2)
C20 O2 C10 C11 173.05(14)
C21 O3 C10 O2 -38.3(2)
C21 O3 C10 C9 -161.94(15)
C21 O3 C10 C11 80.78(19)
C8 C9 C10 O2 52.20(18)
C14 C9 C10 O2 177.12(14)
C8 C9 C10 O3 175.06(13)
C14 C9 C10 O3 -60.02(17)
C8 C9 C10 C11 -64.69(17)
C14 C9 C10 C11 60.23(18)
N1 C11 C10 O2 -70.57(16)
C19 C11 C10 O2 49.94(19)
C12 C11 C10 O2 172.15(13)
N1 C11 C10 O3 166.40(14)
C19 C11 C10 O3 -73.10(19)
C12 C11 C10 O3 49.11(18)
N1 C11 C10 C9 51.49(18)
C19 C11 C10 C9 171.99(15)
C12 C11 C10 C9 -65.80(17)
O4 C13 C12 C11 130.81(19)
C14 C13 C12 C11 -50.2(2)
N1 C11 C12 C13 -58.39(18)
C19 C11 C12 C13 -177.36(15)
C10 C11 C12 C13 59.43(19)
C15 N1 C18 C17 -28.6(2)
C11 N1 C18 C17 152.81(16)
N1 C18 C17 C16 58.4(2)
C15 N2 C16 C17 20.1(2)
C18 C17 C16 N2 -52.97(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203622
