#------------------------------------------------------------------------------
#$Date: 2019-11-11 20:05:47 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/57/4035761.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_4035761
loop_
_publ_author_name
'Yao, Tuanli'
'Guo, Zhen'
'Liang, Xiujuan'
'Qi, Lihan'
_publ_section_title
;
 Regio- and Stereoselective Electrophilic Cyclization Approach for the
 Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine,
 Fumaridine, 8-Oxypseudoplamatine, and 2- O-(Methyloxy)fagaronine.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13370
_journal_page_last               13380
_journal_paper_doi               10.1021/acs.joc.8b02154
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C22 H21 N O7'
_chemical_formula_weight         411.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 128.512(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4582(6)
_cell_length_b                   7.4973(3)
_cell_length_c                   23.2194(7)
_cell_measurement_reflns_used    3404
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.58
_cell_measurement_theta_min      2.82
_cell_volume                     1969.44(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.818
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1219
_diffrn_reflns_av_unetI/netI     0.1882
_diffrn_reflns_Laue_measured_fraction_full 0.818
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17425
_diffrn_reflns_point_group_measured_fraction_full 0.818
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         2.818
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.2153
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1614
_reflns_number_total             4243
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02154_si_002.cif
_cod_data_source_block           SUST_1386_0ma
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035761
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O -0.3410(2) 0.8419(3) -0.01559(13) 0.0618(6) Uani 1 1 d . .
O5 O 0.23979(19) 0.6226(2) -0.01370(11) 0.0482(5) Uani 1 1 d . .
O2 O -0.2769(2) 0.7576(3) -0.08120(12) 0.0602(6) Uani 1 1 d . .
O7 O 0.6808(2) 0.7968(3) 0.23067(12) 0.0559(6) Uani 1 1 d . .
O6 O 0.5050(2) 0.6489(2) 0.09646(11) 0.0507(6) Uani 1 1 d . .
O4 O 0.2470(2) 0.8842(3) 0.31896(14) 0.0735(7) Uani 1 1 d . .
O3 O 0.1128(2) 0.6685(3) 0.25816(13) 0.0730(7) Uani 1 1 d . .
N1 N 0.1585(2) 0.7325(3) 0.03943(13) 0.0417(6) Uani 1 1 d . .
C6 C 0.0169(3) 0.8665(3) 0.09307(16) 0.0404(7) Uani 1 1 d . .
C9 C 0.1407(3) 0.8229(4) 0.26412(17) 0.0469(8) Uani 1 1 d . .
C11 C 0.1428(3) 0.8730(3) 0.12906(16) 0.0422(7) Uani 1 1 d . .
H11 H 0.1884 0.9264 0.1753 0.051 Uiso 1 1 calc R U
C14 C 0.3625(3) 0.7510(3) 0.10959(15) 0.0377(7) Uani 1 1 d . .
C3 C -0.2203(3) 0.8569(4) 0.02825(18) 0.0441(7) Uani 1 1 d . .
C15 C 0.2481(3) 0.6983(3) 0.04157(16) 0.0397(7) Uani 1 1 d . .
C19 C 0.5666(3) 0.8137(3) 0.20551(17) 0.0436(7) Uani 1 1 d . .
C13 C 0.3335(3) 0.8291(3) 0.15155(16) 0.0392(7) Uani 1 1 d . .
C12 C 0.2053(3) 0.8155(3) 0.10743(16) 0.0398(7) Uani 1 1 d . .
C5 C -0.0225(3) 0.9140(3) 0.13330(16) 0.0415(7) Uani 1 1 d . .
C7 C -0.0661(3) 0.8122(3) 0.01891(17) 0.0426(7) Uani 1 1 d . .
H7 H -0.0419 0.7799 -0.0086 0.051 Uiso 1 1 calc R U
C2 C -0.1811(3) 0.8087(3) -0.01077(17) 0.0429(7) Uani 1 1 d . .
C18 C 0.4791(3) 0.7411(3) 0.13618(16) 0.0402(7) Uani 1 1 d . .
C4 C -0.1428(3) 0.9083(4) 0.10003(17) 0.0481(8) Uani 1 1 d . .
H4 H -0.1694 0.9389 0.1263 0.058 Uiso 1 1 calc R U
C8 C 0.0629(3) 0.9704(4) 0.21274(16) 0.0518(8) Uani 1 1 d . .
H8A H 0.1123 1.0656 0.2170 0.062 Uiso 1 1 calc R U
H8B H 0.0185 1.0180 0.2278 0.062 Uiso 1 1 calc R U
C20 C 0.5371(3) 0.8936(3) 0.24622(16) 0.0459(7) Uani 1 1 d . .
H20 H 0.5962 0.9437 0.2918 0.055 Uiso 1 1 calc R U
C21 C 0.4202(3) 0.8994(3) 0.21943(16) 0.0446(7) Uani 1 1 d . .
H21 H 0.4012 0.9504 0.2474 0.054 Uiso 1 1 calc R U
C1 C -0.3782(3) 0.7712(4) -0.08445(18) 0.0544(8) Uani 1 1 d . .
H1A H -0.4138 0.6546 -0.0930 0.065 Uiso 1 1 calc R U
H1B H -0.4363 0.8494 -0.1244 0.065 Uiso 1 1 calc R U
C16 C 0.1211(3) 0.5923(4) -0.08044(16) 0.0533(8) Uani 1 1 d . .
H16A H 0.0780 0.5232 -0.0694 0.080 Uiso 1 1 calc R U
H16B H 0.1241 0.5287 -0.1151 0.080 Uiso 1 1 calc R U
H16C H 0.0822 0.7047 -0.1012 0.080 Uiso 1 1 calc R U
C17 C 0.5636(4) 0.7464(5) 0.0749(2) 0.0748(11) Uani 1 1 d . .
H17A H 0.5183 0.8507 0.0478 0.112 Uiso 1 1 calc R U
H17B H 0.5715 0.6726 0.0443 0.112 Uiso 1 1 calc R U
H17C H 0.6406 0.7817 0.1179 0.112 Uiso 1 1 calc R U
C22 C 0.7723(3) 0.8838(5) 0.29738(19) 0.0688(10) Uani 1 1 d . .
H22A H 0.7520 1.0070 0.2949 0.103 Uiso 1 1 calc R U
H22B H 0.8450 0.8756 0.3044 0.103 Uiso 1 1 calc R U
H22C H 0.7817 0.8276 0.3379 0.103 Uiso 1 1 calc R U
C10 C 0.3303(4) 0.7569(6) 0.3739(2) 0.0988(14) Uani 1 1 d . .
H10A H 0.3076 0.7245 0.4036 0.148 Uiso 1 1 calc R U
H10B H 0.4078 0.8090 0.4046 0.148 Uiso 1 1 calc R U
H10C H 0.3308 0.6525 0.3502 0.148 Uiso 1 1 calc R U
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
C3 O1 C1 106.2(2)
C15 O5 C16 115.6(2)
C2 O2 C1 106.4(2)
C19 O7 C22 118.6(2)
C18 O6 C17 116.5(2)
C9 O4 C10 116.8(3)
C15 N1 C12 105.9(3)
C5 C6 C7 119.6(3)
C5 C6 C11 119.2(3)
C7 C6 C11 121.2(2)
O3 C9 O4 123.2(3)
O3 C9 C8 125.9(3)
O4 C9 C8 110.8(3)
C12 C11 C6 131.6(3)
C12 C11 H11 114.2
C6 C11 H11 114.2
C18 C14 C13 121.1(3)
C18 C14 C15 135.2(2)
C13 C14 C15 103.7(2)
C4 C3 O1 128.9(2)
C4 C3 C2 121.0(3)
O1 C3 C2 110.1(3)
N1 C15 O5 124.0(3)
N1 C15 C14 114.9(2)
O5 C15 C14 121.1(3)
O7 C19 C20 123.2(3)
O7 C19 C18 116.2(2)
C20 C19 C18 120.7(3)
C21 C13 C14 120.3(3)
C21 C13 C12 133.4(2)
C14 C13 C12 106.3(2)
C11 C12 N1 126.2(3)
C11 C12 C13 124.7(3)
N1 C12 C13 109.2(2)
C4 C5 C6 120.2(3)
C4 C5 C8 118.4(2)
C6 C5 C8 121.4(3)
C2 C7 C6 118.0(2)
C2 C7 H7 121.0
C6 C7 H7 121.0
C7 C2 C3 122.6(3)
C7 C2 O2 128.1(2)
C3 C2 O2 109.2(3)
O6 C18 C14 119.3(3)
O6 C18 C19 122.6(3)
C14 C18 C19 118.0(2)
C3 C4 C5 118.6(3)
C3 C4 H4 120.7
C5 C4 H4 120.7
C9 C8 C5 113.9(2)
C9 C8 H8A 108.8
C5 C8 H8A 108.8
C9 C8 H8B 108.8
C5 C8 H8B 108.8
H8A C8 H8B 107.7
C19 C20 C21 120.7(3)
C19 C20 H20 119.7
C21 C20 H20 119.7
C13 C21 C20 119.3(3)
C13 C21 H21 120.4
C20 C21 H21 120.4
O2 C1 O1 108.0(3)
O2 C1 H1A 110.1
O1 C1 H1A 110.1
O2 C1 H1B 110.1
O1 C1 H1B 110.1
H1A C1 H1B 108.4
O5 C16 H16A 109.5
O5 C16 H16B 109.5
H16A C16 H16B 109.5
O5 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O6 C17 H17A 109.5
O6 C17 H17B 109.5
H17A C17 H17B 109.5
O6 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O7 C22 H22A 109.5
O7 C22 H22B 109.5
H22A C22 H22B 109.5
O7 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
O4 C10 H10A 109.5
O4 C10 H10B 109.5
H10A C10 H10B 109.5
O4 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.372(4)
O1 C1 1.434(4)
O5 C15 1.339(3)
O5 C16 1.444(4)
O2 C2 1.385(4)
O2 C1 1.423(3)
O7 C19 1.372(4)
O7 C22 1.422(4)
O6 C18 1.378(3)
O6 C17 1.426(3)
O4 C9 1.326(4)
O4 C10 1.441(4)
O3 C9 1.205(3)
N1 C15 1.290(4)
N1 C12 1.417(4)
C6 C5 1.410(3)
C6 C7 1.413(4)
C6 C11 1.457(4)
C9 C8 1.497(4)
C11 C12 1.348(4)
C11 H11 0.9300
C14 C18 1.390(4)
C14 C13 1.406(3)
C14 C15 1.460(4)
C3 C4 1.362(4)
C3 C2 1.383(4)
C19 C20 1.391(4)
C19 C18 1.397(4)
C13 C21 1.368(4)
C13 C12 1.460(4)
C5 C4 1.396(5)
C5 C8 1.507(4)
C7 C2 1.347(5)
C7 H7 0.9300
C4 H4 0.9300
C8 H8A 0.9700
C8 H8B 0.9700
C20 C21 1.392(4)
C20 H20 0.9300
C21 H21 0.9300
C1 H1A 0.9700
C1 H1B 0.9700
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 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
C10 O4 C9 O3 -1.3(4)
C10 O4 C9 C8 178.3(3)
C5 C6 C11 C12 170.7(3)
C7 C6 C11 C12 -8.7(4)
C1 O1 C3 C4 -176.1(3)
C1 O1 C3 C2 3.2(3)
C12 N1 C15 O5 -178.6(2)
C12 N1 C15 C14 0.6(3)
C16 O5 C15 N1 4.7(4)
C16 O5 C15 C14 -174.4(2)
C18 C14 C15 N1 179.8(3)
C13 C14 C15 N1 -1.2(3)
C18 C14 C15 O5 -1.0(5)
C13 C14 C15 O5 178.0(2)
C22 O7 C19 C20 -8.0(4)
C22 O7 C19 C18 173.7(3)
C18 C14 C13 C21 0.8(4)
C15 C14 C13 C21 -178.3(2)
C18 C14 C13 C12 -179.7(2)
C15 C14 C13 C12 1.1(3)
C6 C11 C12 N1 1.2(5)
C6 C11 C12 C13 -178.6(3)
C15 N1 C12 C11 -179.6(3)
C15 N1 C12 C13 0.2(3)
C21 C13 C12 C11 -1.7(5)
C14 C13 C12 C11 178.9(2)
C21 C13 C12 N1 178.5(3)
C14 C13 C12 N1 -0.9(3)
C7 C6 C5 C4 -0.3(4)
C11 C6 C5 C4 -179.8(2)
C7 C6 C5 C8 179.2(2)
C11 C6 C5 C8 -0.3(4)
C5 C6 C7 C2 0.3(4)
C11 C6 C7 C2 179.7(2)
C6 C7 C2 C3 0.4(4)
C6 C7 C2 O2 -178.8(2)
C4 C3 C2 C7 -1.1(4)
O1 C3 C2 C7 179.5(3)
C4 C3 C2 O2 178.2(3)
O1 C3 C2 O2 -1.1(3)
C1 O2 C2 C7 177.8(3)
C1 O2 C2 C3 -1.5(3)
C17 O6 C18 C14 122.6(3)
C17 O6 C18 C19 -62.8(4)
C13 C14 C18 O6 174.0(2)
C15 C14 C18 O6 -7.2(5)
C13 C14 C18 C19 -0.9(4)
C15 C14 C18 C19 178.0(3)
O7 C19 C18 O6 3.5(4)
C20 C19 C18 O6 -174.9(2)
O7 C19 C18 C14 178.2(2)
C20 C19 C18 C14 -0.2(4)
O1 C3 C4 C5 -179.8(3)
C2 C3 C4 C5 1.0(4)
C6 C5 C4 C3 -0.3(4)
C8 C5 C4 C3 -179.9(2)
O3 C9 C8 C5 -34.7(4)
O4 C9 C8 C5 145.7(3)
C4 C5 C8 C9 110.7(3)
C6 C5 C8 C9 -68.8(3)
O7 C19 C20 C21 -176.9(3)
C18 C19 C20 C21 1.4(4)
C14 C13 C21 C20 0.4(4)
C12 C13 C21 C20 -178.9(3)
C19 C20 C21 C13 -1.5(4)
C2 O2 C1 O1 3.4(3)
C3 O1 C1 O2 -4.1(3)
