#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:22:15 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288742 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/02/1570259.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_1570259
loop_
_publ_author_name
'Zheng, Cheng-Yu'
'Zhao, Jin-Xin'
'Yuan, Chang-Hao'
'Peng, Xia'
'Geng, Meiyu'
'Ai, Jing'
'Fan, Yao-Yue'
'Yue, Jian-Min'
_publ_section_title
;
 Unprecedented sesterterpenoids, orientanoids A-C: discovery, bioinspired
 total synthesis and antitumor immunity.
;
_journal_issue                   46
_journal_name_full               'Chemical science'
_journal_page_first              13410
_journal_page_last               13418
_journal_paper_doi               10.1039/d3sc04238c
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H16 O4'
_chemical_formula_sum            'C15 H16 O4'
_chemical_formula_weight         260.28
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-08 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4619(19)
_cell_length_b                   10.6895(19)
_cell_length_c                   11.617(2)
_cell_measurement_reflns_used    9110
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.224
_cell_measurement_theta_min      3.826
_cell_volume                     1299.2(4)
_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      298
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_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  0.0647
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22909
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.908
_diffrn_reflns_theta_min         5.624
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1539 before and 0.0942 after correction. The Ratio of minimum to maximum transmission is 0.8682. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1023 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0438
_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)+(0.0737P)²+0.1307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1151
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2524
_reflns_number_total             2651
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc04238c2.cif
_cod_data_source_block           cu_22020155_0m
_cod_depositor_comments
'Adding full bibliography for 1570253--1570262.cif.'
_cod_original_cell_volume        1299.1(4)
_cod_database_code               1570259
_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   0.961
_shelx_estimated_absorpt_t_min   0.884
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C6(H6A,H6B), C10(H10A,H10B)
2.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C8(H8A,H8B,H8C)
;
_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
O3 O 0.27283(15) 0.42452(15) 0.12758(13) 0.0405(4) Uani 1 1 d . . . . .
O2 O 0.54159(16) 0.42655(18) 0.24468(16) 0.0510(4) Uani 1 1 d . . . . .
O4 O 0.0045(2) 0.3412(2) 0.56143(18) 0.0613(6) Uani 1 1 d . . . . .
O1 O 0.6776(2) 0.3656(2) 0.1072(3) 0.0800(7) Uani 1 1 d . . . . .
C14 C 0.2582(2) 0.2240(2) 0.2234(2) 0.0412(5) Uani 1 1 d . . . . .
H14A H 0.212052 0.188122 0.158965 0.049 Uiso 1 1 calc R . . . .
H14B H 0.306310 0.158184 0.261174 0.049 Uiso 1 1 calc R . . . .
C13 C 0.1670(2) 0.2843(2) 0.3066(2) 0.0404(5) Uani 1 1 d . . . . .
C12 C 0.1357(2) 0.2485(2) 0.4138(2) 0.0433(5) Uani 1 1 d . . . . .
C11 C 0.0536(2) 0.3459(2) 0.4661(2) 0.0458(5) Uani 1 1 d . . . . .
C9 C 0.1112(2) 0.4101(2) 0.2732(2) 0.0421(5) Uani 1 1 d . . . . .
H9 H 0.046406 0.396370 0.213573 0.051 Uiso 1 1 calc R . . . .
C4 C 0.3477(2) 0.3281(2) 0.18228(18) 0.0357(4) Uani 1 1 d . . . . .
C5 C 0.4124(2) 0.3960(2) 0.2844(2) 0.0401(5) Uani 1 1 d . . . . .
H5 H 0.414547 0.343049 0.353278 0.048 Uiso 1 1 calc R . . . .
C2 C 0.4578(2) 0.2926(2) 0.1068(2) 0.0432(5) Uani 1 1 d . . . . .
C15 C 0.1719(3) 0.1324(3) 0.4757(3) 0.0562(7) Uani 1 1 d . . . . .
H15A H 0.114641 0.066107 0.454401 0.084 Uiso 1 1 calc GR . . . .
H15B H 0.166766 0.146307 0.557169 0.084 Uiso 1 1 calc GR . . . .
H15C H 0.257775 0.109494 0.455453 0.084 Uiso 1 1 calc GR . . . .
C3 C 0.5719(2) 0.3622(2) 0.1486(3) 0.0513(6) Uani 1 1 d . . . . .
C7 C 0.2172(2) 0.4945(2) 0.2226(2) 0.0419(5) Uani 1 1 d . . . . .
C6 C 0.3320(2) 0.5121(2) 0.3037(2) 0.0473(6) Uani 1 1 d . . . . .
H6A H 0.379512 0.587018 0.284071 0.057 Uiso 1 1 calc R . . . .
H6B H 0.304339 0.517730 0.383196 0.057 Uiso 1 1 calc R . . . .
C10 C 0.0435(3) 0.4542(3) 0.3831(2) 0.0513(6) Uani 1 1 d . . . . .
H10A H 0.085078 0.527945 0.414256 0.062 Uiso 1 1 calc R . . . .
H10B H -0.045310 0.474033 0.367476 0.062 Uiso 1 1 calc R . . . .
C1 C 0.4615(3) 0.2123(3) 0.0211(2) 0.0569(7) Uani 1 1 d . . . . .
H1A H 0.538304 0.196550 -0.016597 0.068 Uiso 1 1 calc R . . . .
H1B H 0.387430 0.171153 -0.001797 0.068 Uiso 1 1 calc R . . . .
C8 C 0.1637(3) 0.6154(3) 0.1744(3) 0.0644(8) Uani 1 1 d . . . . .
H8A H 0.232168 0.664877 0.143480 0.097 Uiso 1 1 calc GR . . . .
H8B H 0.121717 0.661079 0.234610 0.097 Uiso 1 1 calc GR . . . .
H8C H 0.103466 0.596701 0.114478 0.097 Uiso 1 1 calc GR . . . .
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 O3 C7 104.50(15) . . ?
C3 O2 C5 111.33(19) . . ?
H14A C14 H14B 108.7 . . ?
C13 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
C13 C14 C4 106.10(17) . . ?
C4 C14 H14A 110.5 . . ?
C4 C14 H14B 110.5 . . ?
C14 C13 C9 117.4(2) . . ?
C12 C13 C14 128.9(2) . . ?
C12 C13 C9 113.36(19) . . ?
C13 C12 C11 108.7(2) . . ?
C13 C12 C15 128.7(2) . . ?
C11 C12 C15 122.5(2) . . ?
O4 C11 C12 126.0(2) . . ?
O4 C11 C10 125.5(2) . . ?
C12 C11 C10 108.5(2) . . ?
C13 C9 H9 108.4 . . ?
C13 C9 C7 109.80(18) . . ?
C13 C9 C10 103.74(19) . . ?
C7 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C10 C9 C7 117.9(2) . . ?
O3 C4 C14 108.95(18) . . ?
O3 C4 C5 103.89(16) . . ?
O3 C4 C2 109.91(17) . . ?
C14 C4 C5 111.66(18) . . ?
C2 C4 C14 118.05(18) . . ?
C2 C4 C5 103.40(18) . . ?
O2 C5 C4 105.46(18) . . ?
O2 C5 H5 111.4 . . ?
O2 C5 C6 112.08(19) . . ?
C4 C5 H5 111.4 . . ?
C6 C5 C4 104.74(17) . . ?
C6 C5 H5 111.4 . . ?
C3 C2 C4 107.4(2) . . ?
C1 C2 C4 129.2(2) . . ?
C1 C2 C3 123.4(2) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C3 C2 109.7(2) . . ?
O1 C3 O2 122.0(3) . . ?
O1 C3 C2 128.3(3) . . ?
O3 C7 C9 105.98(18) . . ?
O3 C7 C6 102.39(17) . . ?
O3 C7 C8 107.76(19) . . ?
C6 C7 C9 113.53(19) . . ?
C8 C7 C9 112.0(2) . . ?
C8 C7 C6 114.2(2) . . ?
C5 C6 C7 104.09(18) . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
C7 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
C11 C10 C9 105.24(19) . . ?
C11 C10 H10A 110.7 . . ?
C11 C10 H10B 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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
O3 C4 1.442(3) . ?
O3 C7 1.455(3) . ?
O2 C5 1.465(3) . ?
O2 C3 1.348(4) . ?
O4 C11 1.222(3) . ?
O1 C3 1.207(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.503(3) . ?
C14 C4 1.531(3) . ?
C13 C12 1.344(3) . ?
C13 C9 1.516(3) . ?
C12 C11 1.480(3) . ?
C12 C15 1.483(4) . ?
C11 C10 1.511(4) . ?
C9 H9 0.9800 . ?
C9 C7 1.546(3) . ?
C9 C10 1.535(3) . ?
C4 C5 1.547(3) . ?
C4 C2 1.496(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.515(3) . ?
C2 C3 1.488(4) . ?
C2 C1 1.315(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C7 C6 1.538(3) . ?
C7 C8 1.515(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
