#------------------------------------------------------------------------------
#$Date: 2021-05-27 02:11:48 +0300 (Thu, 27 May 2021) $
#$Revision: 265512 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/28/1562892.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_1562892
loop_
_publ_author_name
'Cheng, Gui-Guang'
'Liu, Ya-Ping'
'Gu, Ji'
'Qian, Sheng-Yan'
'Yang, Hong-Jun'
'Na, Zhong-Yuan'
'Luo, Xiao-Dong'
_publ_section_title
;
 Phytochemicals and Allelopathy of Induced Water Hyacinth against
 Microcystis aeruginosa.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.1c00075
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 O3'
_chemical_formula_sum            'C21 H20 O3'
_chemical_formula_weight         320.37
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.33390(10)
_cell_length_b                   11.0182(2)
_cell_length_c                   20.2959(4)
_cell_measurement_reflns_used    7274
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.53
_cell_measurement_theta_min      4.36
_cell_volume                     1640.04(5)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8791
_diffrn_reflns_theta_full        69.33
_diffrn_reflns_theta_max         69.33
_diffrn_reflns_theta_min         4.36
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.9041
_exptl_absorpt_correction_T_min  0.7709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0506
_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)+(0.0858P)²+0.2095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1410
_reflns_number_gt                2608
_reflns_number_total             2787
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np1c00075_si_002.cif
_cod_data_source_block           cu_wec22_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 
;
_cod_database_code               1562892
loop_
_symmetry_equiv_pos_as_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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.7932(3) 1.12268(14) 0.35358(7) 0.0671(6) Uani 1 1 d . . .
O9 O 0.7027(3) 0.74144(15) 0.06860(6) 0.0632(5) Uani 1 1 d . . .
H9 H 0.6916 0.6692 0.0599 0.095 Uiso 1 1 calc R . .
O8 O 0.7196(3) 0.54448(14) 0.14041(8) 0.0680(6) Uani 1 1 d . . .
C1 C 0.7298(3) 0.97954(17) 0.11694(9) 0.0404(4) Uani 1 1 d . . .
H1 H 0.6461 0.9611 0.0806 0.049 Uiso 1 1 calc R . .
C1' C 0.9132(3) 1.00962(18) 0.08642(9) 0.0417(5) Uani 1 1 d . . .
C10 C 0.7960(6) 1.1343(2) 0.42343(11) 0.0906(12) Uani 1 1 d . . .
H10A H 0.6954 1.0903 0.4420 0.136 Uiso 1 1 calc R . .
H10B H 0.7863 1.2185 0.4352 0.136 Uiso 1 1 calc R . .
H10C H 0.9083 1.1021 0.4403 0.136 Uiso 1 1 calc R . .
C4 C 0.7860(3) 1.0077(2) 0.32812(10) 0.0484(5) Uani 1 1 d . . .
C3A C 0.7648(3) 0.99940(19) 0.26056(9) 0.0424(4) Uani 1 1 d . . .
C9B C 0.7549(3) 0.88344(18) 0.23105(9) 0.0388(4) Uani 1 1 d . . .
C9A C 0.7341(3) 0.86919(17) 0.16123(9) 0.0387(4) Uani 1 1 d . . .
C2' C 1.0731(3) 0.9498(2) 0.10234(13) 0.0559(6) Uani 1 1 d . . .
H2' H 1.0723 0.8916 0.1355 0.067 Uiso 1 1 calc R . .
C3' C 1.2330(4) 0.9754(3) 0.06983(17) 0.0782(9) Uani 1 1 d . . .
H3' H 1.3389 0.9338 0.0811 0.094 Uiso 1 1 calc R . .
C4' C 1.2384(5) 1.0617(4) 0.02070(18) 0.0922(12) Uani 1 1 d . . .
H4' H 1.3466 1.0784 -0.0014 0.111 Uiso 1 1 calc R . .
C5' C 1.0829(6) 1.1219(3) 0.00525(13) 0.0819(10) Uani 1 1 d . . .
H5' H 1.0853 1.1808 -0.0276 0.098 Uiso 1 1 calc R . .
C6' C 0.9218(4) 1.0975(2) 0.03717(11) 0.0614(7) Uani 1 1 d . . .
H6' H 0.8171 1.1403 0.0258 0.074 Uiso 1 1 calc R . .
C2 C 0.6488(3) 1.08726(19) 0.15469(10) 0.0497(5) Uani 1 1 d . . .
H2A H 0.6536 1.1590 0.1270 0.060 Uiso 1 1 calc R . .
H2B H 0.5217 1.0706 0.1644 0.060 Uiso 1 1 calc R . .
C3 C 0.7493(3) 1.11240(19) 0.21854(10) 0.0492(5) Uani 1 1 d . . .
H3A H 0.8705 1.1426 0.2086 0.059 Uiso 1 1 calc R . .
H3B H 0.6851 1.1748 0.2430 0.059 Uiso 1 1 calc R . .
C9 C 0.7218(3) 0.75544(19) 0.13523(9) 0.0449(5) Uani 1 1 d . . .
C8 C 0.7320(3) 0.65011(19) 0.17539(11) 0.0497(5) Uani 1 1 d . . .
C11 C 0.7195(4) 0.4340(2) 0.17688(14) 0.0679(7) Uani 1 1 d . . .
H11A H 0.8311 0.4274 0.2013 0.102 Uiso 1 1 calc R . .
H11B H 0.7094 0.3666 0.1471 0.102 Uiso 1 1 calc R . .
H11C H 0.6181 0.4334 0.2068 0.102 Uiso 1 1 calc R . .
C7 C 0.7546(3) 0.66053(18) 0.24139(10) 0.0472(5) Uani 1 1 d . . .
H7 H 0.7630 0.5913 0.2674 0.057 Uiso 1 1 calc R . .
C6A C 0.7655(3) 0.77732(18) 0.27085(10) 0.0426(5) Uani 1 1 d . . .
C6 C 0.7883(3) 0.7911(2) 0.33914(10) 0.0500(5) Uani 1 1 d . . .
H6 H 0.7969 0.7225 0.3657 0.060 Uiso 1 1 calc R . .
C5 C 0.7980(3) 0.9031(2) 0.36717(10) 0.0546(6) Uani 1 1 d . . .
H5 H 0.8127 0.9103 0.4125 0.065 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 0.0181 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O4 C10 117.38(17) . . ?
C9 O9 H9 109.5 . . ?
C8 O8 C11 117.27(17) . . ?
C9A C1 C1' 113.57(16) . . ?
C9A C1 C2 109.47(15) . . ?
C1' C1 C2 112.24(17) . . ?
C9A C1 H1 107.1 . . ?
C1' C1 H1 107.1 . . ?
C2 C1 H1 107.1 . . ?
C2' C1' C6' 117.4(2) . . ?
C2' C1' C1 123.50(18) . . ?
C6' C1' C1 119.0(2) . . ?
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 . . ?
O4 C4 C3A 116.10(19) . . ?
O4 C4 C5 123.03(18) . . ?
C3A C4 C5 120.9(2) . . ?
C4 C3A C9B 119.08(19) . . ?
C4 C3A C3 120.84(19) . . ?
C9B C3A C3 120.07(17) . . ?
C3A C9B C6A 119.96(16) . . ?
C3A C9B C9A 121.57(18) . . ?
C6A C9B C9A 118.48(18) . . ?
C9 C9A C9B 119.36(18) . . ?
C9 C9A C1 120.52(17) . . ?
C9B C9A C1 120.11(16) . . ?
C3' C2' C1' 120.9(3) . . ?
C3' C2' H2' 119.5 . . ?
C1' C2' H2' 119.5 . . ?
C2' C3' C4' 120.8(3) . . ?
C2' C3' H3' 119.6 . . ?
C4' C3' H3' 119.6 . . ?
C5' C4' C3' 118.7(3) . . ?
C5' C4' H4' 120.6 . . ?
C3' C4' H4' 120.6 . . ?
C4' C5' C6' 121.2(3) . . ?
C4' C5' H5' 119.4 . . ?
C6' C5' H5' 119.4 . . ?
C5' C6' C1' 120.9(3) . . ?
C5' C6' H6' 119.6 . . ?
C1' C6' H6' 119.6 . . ?
C3 C2 C1 112.35(18) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C3A C3 C2 111.58(18) . . ?
C3A C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C3A C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C9A C9 O9 119.54(18) . . ?
C9A C9 C8 121.73(17) . . ?
O9 C9 C8 118.72(18) . . ?
C7 C8 O8 126.45(19) . . ?
C7 C8 C9 120.31(18) . . ?
O8 C8 C9 113.24(18) . . ?
O8 C11 H11A 109.5 . . ?
O8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C7 C6A 119.98(18) . . ?
C8 C7 H7 120.0 . . ?
C6A C7 H7 120.0 . . ?
C6 C6A C7 121.31(18) . . ?
C6 C6A C9B 118.55(18) . . ?
C7 C6A C9B 120.13(17) . . ?
C5 C6 C6A 121.1(2) . . ?
C5 C6 H6 119.4 . . ?
C6A C6 H6 119.4 . . ?
C6 C5 C4 120.41(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C4 1.369(3) . ?
O4 C10 1.424(3) . ?
O9 C9 1.368(2) . ?
O9 H9 0.8200 . ?
O8 C8 1.366(2) . ?
O8 C11 1.425(3) . ?
C1 C9A 1.512(3) . ?
C1 C1' 1.517(3) . ?
C1 C2 1.533(3) . ?
C1 H1 0.9800 . ?
C1' C2' 1.383(3) . ?
C1' C6' 1.393(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C4 C3A 1.383(3) . ?
C4 C5 1.402(3) . ?
C3A C9B 1.413(3) . ?
C3A C3 1.513(3) . ?
C9B C6A 1.423(3) . ?
C9B C9A 1.434(3) . ?
C9A C9 1.363(3) . ?
C2' C3' 1.375(4) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.379(5) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.356(5) . ?
C4' H4' 0.9300 . ?
C5' C6' 1.374(4) . ?
C5' H5' 0.9300 . ?
C6' H6' 0.9300 . ?
C2 C3 1.516(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 C8 1.420(3) . ?
C8 C7 1.355(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C7 C6A 1.421(3) . ?
C7 H7 0.9300 . ?
C6A C6 1.404(3) . ?
C6 C5 1.361(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
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
O9 H9 O8 0.82 2.15 2.617(2) 116.6 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 C1' C2' -6.1(3) . . . . ?
C2 C1 C1' C2' 118.8(2) . . . . ?
C9A C1 C1' C6' 170.43(18) . . . . ?
C2 C1 C1' C6' -64.7(2) . . . . ?
C10 O4 C4 C3A 173.7(3) . . . . ?
C10 O4 C4 C5 -6.0(4) . . . . ?
O4 C4 C3A C9B -179.49(19) . . . . ?
C5 C4 C3A C9B 0.2(3) . . . . ?
O4 C4 C3A C3 -0.5(3) . . . . ?
C5 C4 C3A C3 179.2(2) . . . . ?
C4 C3A C9B C6A 0.4(3) . . . . ?
C3 C3A C9B C6A -178.62(19) . . . . ?
C4 C3A C9B C9A -179.6(2) . . . . ?
C3 C3A C9B C9A 1.4(3) . . . . ?
C3A C9B C9A C9 -178.83(18) . . . . ?
C6A C9B C9A C9 1.2(3) . . . . ?
C3A C9B C9A C1 2.4(3) . . . . ?
C6A C9B C9A C1 -177.57(17) . . . . ?
C1' C1 C9A C9 -82.6(2) . . . . ?
C2 C1 C9A C9 151.09(19) . . . . ?
C1' C1 C9A C9B 96.1(2) . . . . ?
C2 C1 C9A C9B -30.2(2) . . . . ?
C6' C1' C2' C3' -1.0(3) . . . . ?
C1 C1' C2' C3' 175.5(2) . . . . ?
C1' C2' C3' C4' 0.3(4) . . . . ?
C2' C3' C4' C5' 0.5(4) . . . . ?
C3' C4' C5' C6' -0.5(4) . . . . ?
C4' C5' C6' C1' -0.2(4) . . . . ?
C2' C1' C6' C5' 1.0(3) . . . . ?
C1 C1' C6' C5' -175.7(2) . . . . ?
C9A C1 C2 C3 55.2(2) . . . . ?
C1' C1 C2 C3 -71.9(2) . . . . ?
C4 C3A C3 C2 -155.3(2) . . . . ?
C9B C3A C3 C2 23.7(3) . . . . ?
C1 C2 C3 C3A -52.4(2) . . . . ?
C9B C9A C9 O9 -179.7(2) . . . . ?
C1 C9A C9 O9 -1.0(3) . . . . ?
C9B C9A C9 C8 -1.0(3) . . . . ?
C1 C9A C9 C8 177.73(19) . . . . ?
C11 O8 C8 C7 4.0(4) . . . . ?
C11 O8 C8 C9 -177.0(2) . . . . ?
C9A C9 C8 C7 -0.1(3) . . . . ?
O9 C9 C8 C7 178.7(2) . . . . ?
C9A C9 C8 O8 -179.1(2) . . . . ?
O9 C9 C8 O8 -0.4(3) . . . . ?
O8 C8 C7 C6A 179.9(2) . . . . ?
C9 C8 C7 C6A 1.0(4) . . . . ?
C8 C7 C6A C6 179.8(2) . . . . ?
C8 C7 C6A C9B -0.8(3) . . . . ?
C3A C9B C6A C6 -0.8(3) . . . . ?
C9A C9B C6A C6 179.2(2) . . . . ?
C3A C9B C6A C7 179.7(2) . . . . ?
C9A C9B C6A C7 -0.3(3) . . . . ?
C7 C6A C6 C5 -179.8(2) . . . . ?
C9B C6A C6 C5 0.8(3) . . . . ?
C6A C6 C5 C4 -0.2(4) . . . . ?
O4 C4 C5 C6 179.4(2) . . . . ?
C3A C4 C5 C6 -0.3(4) . . . . ?
