#------------------------------------------------------------------------------
#$Date: 2021-06-04 04:01:59 +0300 (Fri, 04 Jun 2021) $
#$Revision: 265757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/27/1562750.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_1562750
loop_
_publ_author_name
'Wang, Xing'
'Peng, Xia'
'Tang, Chunping'
'Zhou, Shuaizhen'
'Ke, Chang-Qiang'
'Liu, Yueling'
'Yao, Sheng'
'Ai, Jing'
'Ye, Yang'
_publ_section_title
;
 Anti-inflammatory Eudesmane Sesquiterpenoids from Artemisia
 hedinii.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1626
_journal_page_last               1637
_journal_paper_doi               10.1021/acs.jnatprod.1c00177
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H24 O4'
_chemical_formula_sum            'C15 H24 O4'
_chemical_formula_weight         268.34
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4265(2)
_cell_length_b                   9.3215(4)
_cell_length_c                   22.7177(8)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.507
_cell_measurement_theta_min      4.744
_cell_volume                     1360.90(9)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14652
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.619
_diffrn_reflns_theta_min         5.129
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1417 before and 0.0843 after correction. The Ratio of minimum to maximum transmission is 0.5902. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1082 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0381
_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)+(0.0647P)²+0.4518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2698
_reflns_number_total             2741
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np1c00177_si_008.cif
_cod_data_source_block           cu_22020628_0m
_cod_depositor_comments
'Adding full bibliography for 1562743--1562751.cif.'
_cod_database_code               1562750
_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   0.963
_shelx_estimated_absorpt_t_min   0.895
_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 Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C9(H9A,H9B), C1(H1A,H1B), C2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
O2 O 0.4753(3) 0.41741(19) 0.34780(7) 0.0265(4) Uani 1 1 d . . . . .
H2 H 0.593768 0.393548 0.359978 0.040 Uiso 1 1 calc GR . . . .
O4 O -0.1643(3) 0.3305(2) 0.40405(8) 0.0314(4) Uani 1 1 d . . . . .
O3 O 0.1282(3) 0.2920(2) 0.49829(8) 0.0329(4) Uani 1 1 d . . . . .
H3 H 0.168949 0.377487 0.500077 0.049 Uiso 1 1 calc GR . . . .
O1 O 0.7210(4) 0.9279(2) 0.46325(10) 0.0464(6) Uani 1 1 d . . . . .
C6 C 0.3710(3) 0.4991(2) 0.39223(9) 0.0209(5) Uani 1 1 d . . . . .
H6 H 0.415235 0.462177 0.431616 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5709(4) 0.7156(3) 0.42671(10) 0.0236(5) Uani 1 1 d . . . . .
C15 C 0.6662(4) 0.6378(3) 0.47810(11) 0.0307(5) Uani 1 1 d . . . . .
H15A H 0.603761 0.672514 0.514780 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.816515 0.655455 0.478847 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.640457 0.534583 0.474140 0.046 Uiso 1 1 calc GR . . . .
C7 C 0.1338(3) 0.4792(2) 0.38655(9) 0.0212(5) Uani 1 1 d . . . . .
H7 H 0.071291 0.531722 0.420609 0.025 Uiso 1 1 calc R . . . .
C5 C 0.4345(4) 0.6574(2) 0.38773(10) 0.0217(5) Uani 1 1 d . . . . .
C8 C 0.0512(4) 0.5535(3) 0.33131(11) 0.0277(5) Uani 1 1 d . . . . .
H8A H 0.113964 0.509287 0.295879 0.033 Uiso 1 1 calc R . . . .
H8B H -0.101595 0.541369 0.328940 0.033 Uiso 1 1 calc R . . . .
C14 C 0.4473(5) 0.6993(3) 0.27842(11) 0.0352(6) Uani 1 1 d . . . . .
H14A H 0.597558 0.715014 0.281780 0.053 Uiso 1 1 calc GR . . . .
H14B H 0.391789 0.757833 0.246207 0.053 Uiso 1 1 calc GR . . . .
H14C H 0.420333 0.597702 0.270292 0.053 Uiso 1 1 calc GR . . . .
C11 C 0.0557(4) 0.3218(3) 0.39169(10) 0.0238(5) Uani 1 1 d . . . . .
C12 C 0.1624(4) 0.2378(3) 0.44061(10) 0.0270(5) Uani 1 1 d . . . . .
H12A H 0.113218 0.137219 0.439135 0.032 Uiso 1 1 calc R . . . .
H12B H 0.314069 0.236990 0.432910 0.032 Uiso 1 1 calc R . . . .
C3 C 0.6312(4) 0.8686(3) 0.42208(12) 0.0316(6) Uani 1 1 d . . . . .
C10 C 0.3398(4) 0.7424(3) 0.33687(10) 0.0260(5) Uani 1 1 d . . . . .
C9 C 0.1048(4) 0.7120(3) 0.33334(11) 0.0289(5) Uani 1 1 d . . . . .
H9A H 0.035814 0.755583 0.367968 0.035 Uiso 1 1 calc R . . . .
H9B H 0.048079 0.758975 0.297701 0.035 Uiso 1 1 calc R . . . .
C1 C 0.3636(5) 0.9045(3) 0.34656(12) 0.0345(6) Uani 1 1 d . . . . .
H1A H 0.331110 0.955090 0.309345 0.041 Uiso 1 1 calc R . . . .
H1B H 0.261425 0.936126 0.376492 0.041 Uiso 1 1 calc R . . . .
C13 C 0.0752(5) 0.2361(3) 0.33477(11) 0.0334(6) Uani 1 1 d . . . . .
H13A H 0.028320 0.137466 0.341526 0.050 Uiso 1 1 calc GR . . . .
H13B H 0.220882 0.235376 0.322004 0.050 Uiso 1 1 calc GR . . . .
H13C H -0.010985 0.280528 0.304203 0.050 Uiso 1 1 calc GR . . . .
C2 C 0.5820(5) 0.9473(3) 0.36673(14) 0.0386(7) Uani 1 1 d . . . . .
H2A H 0.684946 0.922712 0.335912 0.046 Uiso 1 1 calc R . . . .
H2B H 0.588132 1.051997 0.373720 0.046 Uiso 1 1 calc R . . . .
H4 H -0.194(7) 0.303(5) 0.436(2) 0.058(12) 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 0.0181 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
O2 C6 C7 109.90(18) . . ?
O2 C6 C5 109.89(17) . . ?
C5 C6 C7 111.91(18) . . ?
C5 C4 C15 125.1(2) . . ?
C5 C4 C3 120.4(2) . . ?
C3 C4 C15 114.4(2) . . ?
C6 C7 C11 115.25(18) . . ?
C8 C7 C6 110.97(19) . . ?
C8 C7 C11 112.15(19) . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 C10 122.9(2) . . ?
C10 C5 C6 116.31(19) . . ?
C9 C8 C7 109.7(2) . . ?
O4 C11 C7 106.14(18) . . ?
O4 C11 C12 109.1(2) . . ?
O4 C11 C13 105.9(2) . . ?
C12 C11 C7 113.24(19) . . ?
C12 C11 C13 108.2(2) . . ?
C13 C11 C7 113.8(2) . . ?
O3 C12 C11 114.8(2) . . ?
O1 C3 C4 120.0(3) . . ?
O1 C3 C2 121.4(3) . . ?
C4 C3 C2 118.6(2) . . ?
C5 C10 C14 109.7(2) . . ?
C5 C10 C9 109.6(2) . . ?
C5 C10 C1 111.3(2) . . ?
C9 C10 C14 110.2(2) . . ?
C1 C10 C14 109.5(2) . . ?
C1 C10 C9 106.6(2) . . ?
C8 C9 C10 113.8(2) . . ?
C2 C1 C10 113.0(2) . . ?
C3 C2 C1 108.6(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
O2 C6 1.431(3) . ?
O4 C11 1.444(3) . ?
O3 C12 1.421(3) . ?
O1 C3 1.230(3) . ?
C6 C7 1.541(3) . ?
C6 C5 1.535(3) . ?
C4 C15 1.505(3) . ?
C4 C5 1.359(3) . ?
C4 C3 1.481(4) . ?
C7 C8 1.528(3) . ?
C7 C11 1.555(3) . ?
C5 C10 1.527(3) . ?
C8 C9 1.518(4) . ?
C14 C10 1.550(3) . ?
C11 C12 1.523(3) . ?
C11 C13 1.525(3) . ?
C3 C2 1.489(4) . ?
C10 C9 1.539(4) . ?
C10 C1 1.535(4) . ?
C1 C2 1.529(4) . ?
