#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:19:35 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157923.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_7157923
loop_
_publ_author_name
'Liang, Leilei'
'Li, Ji'
'Shen, Baochun'
'Zhang, Yili'
'Liu, Jianping'
'Chen, Jingbo'
'Liu, Dandan'
_publ_section_title
;
 The effect of carbonyl on the isomerization of a galanthan ring system
 and total synthesis of (+-)-β-lycorane.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2767
_journal_page_last               2772
_journal_paper_doi               10.1039/d0ob02398a
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H17 N O4'
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_weight         287.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc25fpfr
_audit_update_record
;
2020-06-10 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2488(2)
_cell_length_b                   7.5956(3)
_cell_length_c                   33.4224(12)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      72.3507
_cell_measurement_theta_min      2.6441
_cell_volume                     1332.48(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11774
_diffrn_reflns_theta_full        72.34
_diffrn_reflns_theta_max         72.34
_diffrn_reflns_theta_min         2.64
_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.169
_refine_ls_abs_structure_details
;

Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0417P)²+0.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                2600
_reflns_number_total             2637
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02398a2.cif
_cod_data_source_block           qlll1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157923.cif.
;
_cod_database_code               7157923
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6712(3) 0.84689(16) 0.71180(4) 0.0302(3) Uani d . . . 1 . .
O O2 0.8112(3) 0.58788(17) 0.74074(4) 0.0300(3) Uani d . . . 1 . .
O O3 0.1291(2) 0.69300(17) 0.50754(3) 0.0242(3) Uani d . . . 1 . .
H H17 0.011007 0.724947 0.4922 0.036 Uiso calc U . R 1 . .
O O4 0.4242(2) 0.67484(15) 0.57184(3) 0.0216(2) Uani d . . . 1 . .
N N1 0.1940(3) 0.22477(18) 0.60836(4) 0.0206(3) Uani d . . . 1 . .
C C1 -0.0261(3) 0.4109(2) 0.53334(5) 0.0237(3) Uani d . . . 1 . .
H H13 -0.137761 0.398915 0.509627 0.028 Uiso calc U . R 1 . .
H H1 0.137172 0.351236 0.527328 0.028 Uiso calc U . R 1 . .
C C2 -0.1523(3) 0.3211(2) 0.56920(5) 0.0219(3) Uani d . . . 1 . .
H H5 -0.333709 0.359946 0.571596 0.026 Uiso calc U . R 1 . .
C C3 -0.0097(3) 0.3564(2) 0.60860(5) 0.0192(3) Uani d . . . 1 . .
H H15 -0.1269 0.330715 0.63145 0.023 Uiso calc U . R 1 . .
C C4 0.1049(3) 0.5405(2) 0.61452(4) 0.0190(3) Uani d . . . 1 . .
H H16 -0.037196 0.619741 0.623045 0.023 Uiso calc U . R 1 . .
C C5 0.3008(3) 0.5417(2) 0.64788(4) 0.0194(3) Uani d . . . 1 . .
C C6 0.3873(3) 0.7056(2) 0.66223(5) 0.0233(3) Uani d . . . 1 . .
H H4 0.325607 0.812915 0.651288 0.028 Uiso calc U . R 1 . .
C C7 0.5633(3) 0.7051(2) 0.69245(5) 0.0238(3) Uani d . . . 1 . .
C C8 0.8697(3) 0.7715(2) 0.73583(5) 0.0284(4) Uani d . . . 1 . .
H H3 0.877213 0.830516 0.762207 0.034 Uiso calc U . R 1 . .
H H2 1.036685 0.785686 0.722439 0.034 Uiso calc U . R 1 . .
C C9 0.6493(3) 0.5496(2) 0.70956(5) 0.0238(3) Uani d . . . 1 . .
C C10 -0.1388(4) 0.1180(2) 0.56580(5) 0.0276(4) Uani d . . . 1 . .
H H6 -0.304504 0.064303 0.572924 0.033 Uiso calc U . R 1 . .
H H12 -0.093446 0.082272 0.538223 0.033 Uiso calc U . R 1 . .
C C11 0.0687(4) 0.0611(2) 0.59539(5) 0.0283(4) Uani d . . . 1 . .
H H7 -0.00739 -0.000925 0.618548 0.034 Uiso calc U . R 1 . .
H H11 0.192527 -0.018387 0.582252 0.034 Uiso calc U . R 1 . .
C C12 0.3113(3) 0.2085(2) 0.64760(5) 0.0231(3) Uani d . . . 1 . .
H H8 0.461139 0.129751 0.645701 0.028 Uiso calc U . R 1 . .
H H9 0.188188 0.154336 0.666354 0.028 Uiso calc U . R 1 . .
C C13 0.3946(3) 0.3855(2) 0.66387(4) 0.0207(3) Uani d . . . 1 . .
C C14 0.5703(3) 0.3883(2) 0.69591(5) 0.0234(3) Uani d . . . 1 . .
H H10 0.631397 0.282321 0.707563 0.028 Uiso calc U . R 1 . .
C C15 0.0244(3) 0.6069(2) 0.54127(4) 0.0203(3) Uani d . . . 1 . .
H H14 -0.13804 0.66609 0.549231 0.024 Uiso calc U . R 1 . .
C C16 0.2112(3) 0.6150(2) 0.57540(5) 0.0177(3) Uani d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C8 . . 104.42(14) ?
C9 O2 C8 . . 104.51(14) ?
C15 O3 H17 . . 109.5 ?
C12 N1 C3 . . 111.24(12) ?
C12 N1 C11 . . 112.52(13) ?
C3 N1 C11 . . 104.60(13) ?
C2 C1 C15 . . 111.83(13) ?
C2 C1 H13 . . 109.3 ?
C15 C1 H13 . . 109.3 ?
C2 C1 H1 . . 109.3 ?
C15 C1 H1 . . 109.3 ?
H13 C1 H1 . . 107.9 ?
C1 C2 C3 . . 112.47(13) ?
C1 C2 C10 . . 111.52(14) ?
C3 C2 C10 . . 102.36(13) ?
C1 C2 H5 . . 110.1 ?
C3 C2 H5 . . 110.1 ?
C10 C2 H5 . . 110.1 ?
N1 C3 C4 . . 109.67(13) ?
N1 C3 C2 . . 103.40(13) ?
C4 C3 C2 . . 117.38(13) ?
N1 C3 H15 . . 108.7 ?
C4 C3 H15 . . 108.7 ?
C2 C3 H15 . . 108.7 ?
C5 C4 C16 . . 112.27(13) ?
C5 C4 C3 . . 111.48(13) ?
C16 C4 C3 . . 111.68(12) ?
C5 C4 H16 . . 107.0 ?
C16 C4 H16 . . 107.0 ?
C3 C4 H16 . . 107.0 ?
C13 C5 C6 . . 120.58(15) ?
C13 C5 C4 . . 121.13(14) ?
C6 C5 C4 . . 118.29(14) ?
C7 C6 C5 . . 117.77(15) ?
C7 C6 H4 . . 121.1 ?
C5 C6 H4 . . 121.1 ?
C6 C7 O1 . . 128.42(16) ?
C6 C7 C9 . . 121.75(16) ?
O1 C7 C9 . . 109.76(14) ?
O1 C8 O2 . . 107.23(14) ?
O1 C8 H3 . . 110.3 ?
O2 C8 H3 . . 110.3 ?
O1 C8 H2 . . 110.3 ?
O2 C8 H2 . . 110.3 ?
H3 C8 H2 . . 108.5 ?
C14 C9 O2 . . 128.87(16) ?
C14 C9 C7 . . 121.66(15) ?
O2 C9 C7 . . 109.46(15) ?
C11 C10 C2 . . 105.45(14) ?
C11 C10 H6 . . 110.7 ?
C2 C10 H6 . . 110.7 ?
C11 C10 H12 . . 110.7 ?
C2 C10 H12 . . 110.7 ?
H6 C10 H12 . . 108.8 ?
N1 C11 C10 . . 105.61(13) ?
N1 C11 H7 . . 110.6 ?
C10 C11 H7 . . 110.6 ?
N1 C11 H11 . . 110.6 ?
C10 C11 H11 . . 110.6 ?
H7 C11 H11 . . 108.8 ?
N1 C12 C13 . . 111.76(13) ?
N1 C12 H8 . . 109.3 ?
C13 C12 H8 . . 109.3 ?
N1 C12 H9 . . 109.3 ?
C13 C12 H9 . . 109.3 ?
H8 C12 H9 . . 107.9 ?
C5 C13 C14 . . 120.59(15) ?
C5 C13 C12 . . 121.12(14) ?
C14 C13 C12 . . 118.29(14) ?
C9 C14 C13 . . 117.57(15) ?
C9 C14 H10 . . 121.2 ?
C13 C14 H10 . . 121.2 ?
O3 C15 C16 . . 109.39(13) ?
O3 C15 C1 . . 112.21(13) ?
C16 C15 C1 . . 106.44(13) ?
O3 C15 H14 . . 109.6 ?
C16 C15 H14 . . 109.6 ?
C1 C15 H14 . . 109.6 ?
O4 C16 C15 . . 122.78(14) ?
O4 C16 C4 . . 123.94(14) ?
C15 C16 C4 . . 113.27(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.378(2) ?
O1 C8 . 1.435(2) ?
O2 C9 . 1.376(2) ?
O2 C8 . 1.437(2) ?
O3 C15 . 1.4147(18) ?
O3 H17 . 0.84 ?
O4 C16 . 1.213(2) ?
N1 C12 . 1.454(2) ?
N1 C3 . 1.464(2) ?
N1 C11 . 1.472(2) ?
C1 C2 . 1.530(2) ?
C1 C15 . 1.535(2) ?
C1 H13 . 0.99 ?
C1 H1 . 0.99 ?
C2 C3 . 1.538(2) ?
C2 C10 . 1.548(2) ?
C2 H5 . 1.0 ?
C3 C4 . 1.535(2) ?
C3 H15 . 1.0 ?
C4 C5 . 1.517(2) ?
C4 C16 . 1.530(2) ?
C4 H16 . 1.0 ?
C5 C13 . 1.392(2) ?
C5 C6 . 1.409(2) ?
C6 C7 . 1.369(2) ?
C6 H4 . 0.95 ?
C7 C9 . 1.388(3) ?
C8 H3 . 0.99 ?
C8 H2 . 0.99 ?
C9 C14 . 1.372(3) ?
C10 C11 . 1.533(2) ?
C10 H6 . 0.99 ?
C10 H12 . 0.99 ?
C11 H7 . 0.99 ?
C11 H11 . 0.99 ?
C12 C13 . 1.514(2) ?
C12 H8 . 0.99 ?
C12 H9 . 0.99 ?
C13 C14 . 1.413(2) ?
C14 H10 . 0.95 ?
C15 C16 . 1.505(2) ?
C15 H14 . 1.0 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H17 O3 2_466 0.84 2.10 2.8091(9) 142.0 ?
O3 H17 O4 2_466 0.84 2.32 3.0334(15) 143.5 ?
C11 H11 O4 1_545 0.99 2.65 3.565(2) 153.6 ?
C15 H14 O3 2_466 1.00 2.50 3.0458(19) 114.1 ?
C15 H14 O4 1_455 1.00 2.42 3.3516(19) 154.8 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C15 C1 C2 C3 . . . . -50.74(19) ?
C15 C1 C2 C10 . . . . -165.07(14) ?
C12 N1 C3 C4 . . . . 68.13(16) ?
C11 N1 C3 C4 . . . . -170.14(12) ?
C12 N1 C3 C2 . . . . -165.91(13) ?
C11 N1 C3 C2 . . . . -44.18(15) ?
C1 C2 C3 N1 . . . . -83.32(16) ?
C10 C2 C3 N1 . . . . 36.48(15) ?
C1 C2 C3 C4 . . . . 37.55(19) ?
C10 C2 C3 C4 . . . . 157.35(14) ?
N1 C3 C4 C5 . . . . -45.87(16) ?
C2 C3 C4 C5 . . . . -163.41(13) ?
N1 C3 C4 C16 . . . . 80.62(15) ?
C2 C3 C4 C16 . . . . -36.92(19) ?
C16 C4 C5 C13 . . . . -113.73(16) ?
C3 C4 C5 C13 . . . . 12.4(2) ?
C16 C4 C5 C6 . . . . 65.88(18) ?
C3 C4 C5 C6 . . . . -167.96(14) ?
C13 C5 C6 C7 . . . . -0.7(2) ?
C4 C5 C6 C7 . . . . 179.73(14) ?
C5 C6 C7 O1 . . . . -178.48(15) ?
C5 C6 C7 C9 . . . . -2.0(2) ?
C8 O1 C7 C6 . . . . -171.00(17) ?
C8 O1 C7 C9 . . . . 12.20(18) ?
C7 O1 C8 O2 . . . . -20.54(17) ?
C9 O2 C8 O1 . . . . 21.15(17) ?
C8 O2 C9 C14 . . . . 167.57(17) ?
C8 O2 C9 C7 . . . . -13.70(17) ?
C6 C7 C9 C14 . . . . 2.8(3) ?
O1 C7 C9 C14 . . . . 179.83(15) ?
C6 C7 C9 O2 . . . . -176.07(15) ?
O1 C7 C9 O2 . . . . 0.98(19) ?
C1 C2 C10 C11 . . . . 104.59(16) ?
C3 C2 C10 C11 . . . . -15.87(17) ?
C12 N1 C11 C10 . . . . 154.57(14) ?
C3 N1 C11 C10 . . . . 33.68(17) ?
C2 C10 C11 N1 . . . . -10.00(19) ?
C3 N1 C12 C13 . . . . -52.11(18) ?
C11 N1 C12 C13 . . . . -169.11(14) ?
C6 C5 C13 C14 . . . . 2.7(2) ?
C4 C5 C13 C14 . . . . -177.73(14) ?
C6 C5 C13 C12 . . . . -177.49(15) ?
C4 C5 C13 C12 . . . . 2.1(2) ?
N1 C12 C13 C5 . . . . 17.0(2) ?
N1 C12 C13 C14 . . . . -163.14(14) ?
O2 C9 C14 C13 . . . . 177.89(16) ?
C7 C9 C14 C13 . . . . -0.7(2) ?
C5 C13 C14 C9 . . . . -2.0(2) ?
C12 C13 C14 C9 . . . . 178.21(14) ?
C2 C1 C15 O3 . . . . -176.97(12) ?
C2 C1 C15 C16 . . . . 63.41(17) ?
O3 C15 C16 O4 . . . . -5.5(2) ?
C1 C15 C16 O4 . . . . 115.90(16) ?
O3 C15 C16 C4 . . . . 174.53(13) ?
C1 C15 C16 C4 . . . . -64.03(16) ?
C5 C4 C16 O4 . . . . -2.8(2) ?
C3 C4 C16 O4 . . . . -128.86(15) ?
C5 C4 C16 C15 . . . . 177.13(13) ?
C3 C4 C16 C15 . . . . 51.07(18) ?
