#------------------------------------------------------------------------------
#$Date: 2020-08-04 05:17:18 +0300 (Tue, 04 Aug 2020) $
#$Revision: 254776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/85/1558580.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_1558580
loop_
_publ_author_name
'Mao, Xu-Dong'
'Zhang, Cheng-Gang'
'Chen, Ting'
'Zhao, Sen-Miao'
'Chou, Gui-Xin'
_publ_section_title
;
 Cytotoxic Diterpenoids from Caryopteris aureoglandulosa.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              2093
_journal_page_last               2101
_journal_paper_doi               10.1021/acs.jnatprod.9b01052
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H18 O5'
_chemical_formula_sum            'C20 H18 O5'
_chemical_formula_weight         338.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.7600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5220(3)
_cell_length_b                   13.0651(2)
_cell_length_c                   7.04120(10)
_cell_measurement_reflns_used    5063
_cell_measurement_temperature    296
_cell_measurement_theta_max      54.545
_cell_measurement_theta_min      7.071
_cell_volume                     1655.01(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9333
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.863
_diffrn_reflns_theta_min         7.069
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1423 before and 0.0586 after correction. The Ratio of minimum to maximum transmission is 0.8290. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0376
_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)+(0.0570P)²+0.1192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                2641
_reflns_number_total             2945
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np9b01052_si_002.cif
_cod_data_source_block           mjr18011_0m
_cod_depositor_comments
'Adding full bibliography for 1558578--1558581.cif.'
_cod_database_code               1558580
_shelx_shelxl_version_number     2018/3
_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_max   0.995
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C15(H15)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.55101(17) 0.89493(17) 0.5120(5) 0.0863(8) Uani 1 1 d . . . . .
O2 O 0.63080(10) 0.72300(16) 0.7231(3) 0.0559(5) Uani 1 1 d . . . . .
H2 H 0.663962 0.682134 0.769048 0.084 Uiso 1 1 calc GR . . . .
O3 O 0.69495(10) 0.54667(16) 0.7946(3) 0.0628(6) Uani 1 1 d . . . . .
O4 O 0.57143(11) 0.24627(14) 0.6036(3) 0.0517(5) Uani 1 1 d . . . . .
O5 O 0.43929(10) 0.35877(14) 0.4250(3) 0.0516(5) Uani 1 1 d . . . . .
C10 C 0.51037(18) 0.8437(2) 0.5843(4) 0.0565(7) Uani 1 1 d . . . . .
C1 C 0.4643(2) 0.8863(2) 0.7132(5) 0.0689(9) Uani 1 1 d . . . . .
H1A H 0.483273 0.953312 0.759171 0.083 Uiso 1 1 calc R . . . .
H1B H 0.469044 0.842312 0.826450 0.083 Uiso 1 1 calc R . . . .
C2 C 0.3823(2) 0.8959(2) 0.6102(6) 0.0723(9) Uani 1 1 d . . . . .
H2A H 0.356446 0.926666 0.700483 0.087 Uiso 1 1 calc R . . . .
H2B H 0.378023 0.942565 0.500898 0.087 Uiso 1 1 calc R . . . .
C3 C 0.34315(19) 0.7968(3) 0.5343(5) 0.0633(8) Uani 1 1 d . . . . .
H3A H 0.290538 0.811648 0.489062 0.076 Uiso 1 1 calc R . . . .
H3B H 0.348647 0.750202 0.644046 0.076 Uiso 1 1 calc R . . . .
C4 C 0.36785(17) 0.7397(2) 0.3689(4) 0.0546(7) Uani 1 1 d . . . . .
C5 C 0.43973(15) 0.6804(2) 0.4531(4) 0.0428(6) Uani 1 1 d . . . . .
C20 C 0.44039(14) 0.57319(19) 0.4400(3) 0.0412(6) Uani 1 1 d . . . . .
H20 H 0.397486 0.539511 0.374150 0.049 Uiso 1 1 calc R . . . .
C9 C 0.50265(13) 0.51642(18) 0.5217(3) 0.0356(5) Uani 1 1 d . . . . .
C8 C 0.56890(14) 0.56454(19) 0.6180(4) 0.0370(5) Uani 1 1 d . . . . .
C6 C 0.50551(14) 0.72910(19) 0.5493(4) 0.0428(6) Uani 1 1 d . . . . .
C14 C 0.63626(12) 0.5055(2) 0.7084(3) 0.0429(6) Uani 1 1 d . . . . .
C13 C 0.62938(14) 0.3943(2) 0.6925(4) 0.0427(6) Uani 1 1 d . . . . .
C12 C 0.56447(15) 0.3498(2) 0.6005(4) 0.0429(6) Uani 1 1 d . . . . .
C11 C 0.49623(13) 0.40227(18) 0.5076(3) 0.0383(5) Uani 1 1 d . . . . .
C15 C 0.68090(16) 0.3134(2) 0.7563(4) 0.0535(7) Uani 1 1 d . . . . .
H15 H 0.730319 0.320006 0.824085 0.064 Uiso 1 1 calc R . . . .
C16 C 0.64400(17) 0.2252(2) 0.6993(4) 0.0576(8) Uani 1 1 d . . . . .
C17 C 0.6649(2) 0.1154(3) 0.7139(7) 0.0873(12) Uani 1 1 d . . . . .
H17A H 0.632377 0.078691 0.777493 0.131 Uiso 1 1 calc GR . . . .
H17B H 0.715265 0.108417 0.788407 0.131 Uiso 1 1 calc GR . . . .
H17C H 0.660525 0.088022 0.585110 0.131 Uiso 1 1 calc GR . . . .
C18 C 0.30493(19) 0.6676(3) 0.2707(6) 0.0791(11) Uani 1 1 d . . . . .
H18A H 0.320498 0.627405 0.173502 0.119 Uiso 1 1 calc GR . . . .
H18B H 0.261922 0.707063 0.209817 0.119 Uiso 1 1 calc GR . . . .
H18C H 0.292876 0.623124 0.367230 0.119 Uiso 1 1 calc GR . . . .
C19 C 0.3785(2) 0.8152(3) 0.2092(5) 0.0732(9) Uani 1 1 d . . . . .
H19A H 0.420809 0.857972 0.260359 0.110 Uiso 1 1 calc GR . . . .
H19B H 0.334924 0.856942 0.169034 0.110 Uiso 1 1 calc GR . . . .
H19C H 0.386498 0.777523 0.098885 0.110 Uiso 1 1 calc GR . . . .
C7 C 0.56926(14) 0.6714(2) 0.6284(4) 0.0412(5) Uani 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 0.0150 0.0070 '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 0.0410 0.0250 '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
C7 O2 H2 109.5 . . ?
C12 O4 C16 106.5(2) . . ?
O1 C10 C1 123.6(3) . . ?
O1 C10 C6 119.9(3) . . ?
C1 C10 C6 116.5(3) . . ?
C10 C1 H1A 109.0 . . ?
C10 C1 H1B 109.0 . . ?
C10 C1 C2 113.0(3) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 C1 115.9(3) . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C2 C3 H3A 107.7 . . ?
C2 C3 H3B 107.7 . . ?
C2 C3 C4 118.4(3) . . ?
H3A C3 H3B 107.1 . . ?
C4 C3 H3A 107.7 . . ?
C4 C3 H3B 107.7 . . ?
C3 C4 C19 110.7(3) . . ?
C5 C4 C3 109.8(2) . . ?
C5 C4 C19 110.8(3) . . ?
C18 C4 C3 108.0(3) . . ?
C18 C4 C5 111.2(2) . . ?
C18 C4 C19 106.3(3) . . ?
C20 C5 C4 120.0(2) . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 C20 117.8(2) . . ?
C5 C20 H20 119.0 . . ?
C9 C20 C5 122.0(2) . . ?
C9 C20 H20 119.0 . . ?
C20 C9 C8 120.7(2) . . ?
C20 C9 C11 117.6(2) . . ?
C8 C9 C11 121.7(2) . . ?
C9 C8 C14 121.8(2) . . ?
C7 C8 C9 117.8(2) . . ?
C7 C8 C14 120.4(2) . . ?
C5 C6 C10 122.6(2) . . ?
C5 C6 C7 120.2(2) . . ?
C7 C6 C10 117.1(2) . . ?
O3 C14 C8 122.6(3) . . ?
O3 C14 C13 121.4(2) . . ?
C13 C14 C8 115.9(2) . . ?
C12 C13 C14 121.0(2) . . ?
C12 C13 C15 106.6(3) . . ?
C15 C13 C14 132.4(3) . . ?
O4 C12 C11 123.2(2) . . ?
C13 C12 O4 110.5(2) . . ?
C13 C12 C11 126.3(2) . . ?
O5 C11 C9 122.9(2) . . ?
O5 C11 C12 123.9(2) . . ?
C12 C11 C9 113.2(2) . . ?
C13 C15 H15 126.7 . . ?
C16 C15 C13 106.6(3) . . ?
C16 C15 H15 126.7 . . ?
O4 C16 C17 115.7(3) . . ?
C15 C16 O4 109.9(3) . . ?
C15 C16 C17 134.4(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C18 H18A 109.5 . . ?
C4 C18 H18B 109.5 . . ?
C4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C7 C8 121.0(2) . . ?
O2 C7 C6 117.3(2) . . ?
C8 C7 C6 121.6(2) . . ?
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
O1 C10 1.207(4) . ?
O2 H2 0.8200 . ?
O2 C7 1.356(3) . ?
O3 C14 1.235(3) . ?
O4 C12 1.358(3) . ?
O4 C16 1.381(3) . ?
O5 C11 1.217(3) . ?
C10 C1 1.493(5) . ?
C10 C6 1.516(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.524(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.518(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.541(4) . ?
C4 C5 1.533(4) . ?
C4 C18 1.530(5) . ?
C4 C19 1.543(5) . ?
C5 C20 1.403(4) . ?
C5 C6 1.399(4) . ?
C20 H20 0.9300 . ?
C20 C9 1.377(3) . ?
C9 C8 1.402(3) . ?
C9 C11 1.498(3) . ?
C8 C14 1.476(3) . ?
C8 C7 1.397(3) . ?
C6 C7 1.400(4) . ?
C14 C13 1.461(4) . ?
C13 C12 1.354(4) . ?
C13 C15 1.423(4) . ?
C12 C11 1.450(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.351(5) . ?
C16 C17 1.483(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
_geom_hbond_publ_flag
O2 H2 O3 0.82 1.86 2.586(3) 147.6 . yes
