#------------------------------------------------------------------------------
#$Date: 2021-04-11 03:53:25 +0300 (Sun, 11 Apr 2021) $
#$Revision: 264044 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/16/1561641.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_1561641
loop_
_publ_author_name
'Wang, Ru-Bing'
'Ma, Shuanggang'
'Jamieson, Cooper S.'
'Gao, Rong-Mei'
'Liu, Yunbao'
'Li, Yong'
'Wang, Xiaojing'
'Li, Yuhuan'
'Houk, Kendall N.'
'Qu, Jing'
'Yu, Shi-shan'
_publ_section_title
;
 Library construction of stereochemically diverse isomers of
 spirooliganin: their total synthesis and antiviral activity
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01277K
_journal_year                    2021
_chemical_formula_sum            'C21 H30 O3'
_chemical_formula_weight         330.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-06-13 deposited with the CCDC.	2021-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                110.674(2)
_cell_angle_beta                 101.373(2)
_cell_angle_gamma                97.790(2)
_cell_formula_units_Z            2
_cell_length_a                   6.03390(10)
_cell_length_b                   11.8215(3)
_cell_length_c                   13.8305(3)
_cell_measurement_temperature    100(2)
_cell_volume                     881.95(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13537
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.839
_diffrn_reflns_theta_max         66.839
_diffrn_reflns_theta_min         3.542
_exptl_absorpt_coefficient_mu    0.639
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0425
_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)+(0.0657P)²+0.2824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2867
_reflns_number_total             3088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc01277k2.cif
_cod_data_source_block           fgh_
_cod_database_code               1561641
_shelx_shelxl_version_number     2014/7
_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_min   0.802
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.91815(16) 0.68964(9) 0.29018(7) 0.0238(2) Uani 1 1 d . . . . .
O2 O 0.33926(14) 0.31850(8) 0.11139(7) 0.0177(2) Uani 1 1 d . . . . .
O3 O -0.13157(15) 0.01891(9) 0.16348(8) 0.0261(2) Uani 1 1 d . . . . .
C1 C 0.7271(2) 0.63235(12) 0.22884(10) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.5695(2) 0.69718(12) 0.17810(11) 0.0219(3) Uani 1 1 d . . . . .
H2A H 0.6049 0.6935 0.1103 0.026 Uiso 1 1 calc R U . . .
H2B H 0.6016 0.7856 0.2267 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3132(2) 0.63969(12) 0.15497(10) 0.0213(3) Uani 1 1 d . . . . .
H3A H 0.2704 0.6560 0.2234 0.026 Uiso 1 1 calc R U . . .
H3B H 0.2186 0.6784 0.1141 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2618(2) 0.50035(12) 0.09081(10) 0.0188(3) Uani 1 1 d . . . . .
H4A H 0.1025 0.4629 0.0881 0.023 Uiso 1 1 calc R U . . .
H4B H 0.2693 0.4845 0.0164 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4308(2) 0.43981(12) 0.13902(9) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.6474(2) 0.49956(12) 0.20127(10) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.8091(2) 0.43383(12) 0.24721(10) 0.0182(3) Uani 1 1 d . . . . .
H7A H 0.8914 0.4878 0.3226 0.022 Uiso 1 1 calc R U . . .
H7B H 0.9265 0.4168 0.2062 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6747(2) 0.31160(11) 0.24251(10) 0.0162(3) Uani 1 1 d . . . . .
H8 H 0.7891 0.2594 0.2499 0.019 Uiso 1 1 calc R U . . .
C9 C 0.5662(2) 0.33447(11) 0.33677(9) 0.0167(3) Uani 1 1 d . . . . .
H9A H 0.4581 0.3898 0.3337 0.020 Uiso 1 1 calc R U . . .
H9B H 0.6899 0.3771 0.4047 0.020 Uiso 1 1 calc R U . . .
C10 C 0.4344(2) 0.21359(11) 0.33618(10) 0.0162(3) Uani 1 1 d . . . . .
H10 H 0.5430 0.1561 0.3300 0.019 Uiso 1 1 calc R U . . .
C11 C 0.3570(2) 0.22914(12) 0.44078(10) 0.0188(3) Uani 1 1 d . . . . .
C12 C 0.3284(2) 0.10575(13) 0.45763(11) 0.0257(3) Uani 1 1 d . . . . .
H12A H 0.4785 0.0804 0.4600 0.031 Uiso 1 1 calc R U . . .
H12B H 0.3008 0.1234 0.5292 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1396(3) -0.00548(14) 0.37731(12) 0.0282(3) Uani 1 1 d . . . . .
H13A H -0.0131 0.0155 0.3800 0.034 Uiso 1 1 calc R U . . .
H13B H 0.1460 -0.0758 0.4000 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1550(2) -0.04835(12) 0.26031(11) 0.0244(3) Uani 1 1 d . . . . .
H14A H 0.3175 -0.0498 0.2579 0.029 Uiso 1 1 calc R U . . .
H14B H 0.0587 -0.1333 0.2181 0.029 Uiso 1 1 calc R U . . .
C15 C 0.0699(2) 0.04007(12) 0.21320(10) 0.0194(3) Uani 1 1 d . . . . .
C16 C 0.2381(2) 0.15716(11) 0.23070(10) 0.0167(3) Uani 1 1 d . . . . .
H16 H 0.1464 0.2213 0.2297 0.020 Uiso 1 1 calc R U . . .
C17 C 0.3415(2) 0.12787(12) 0.13337(10) 0.0177(3) Uani 1 1 d . . . . .
H17A H 0.4321 0.0638 0.1325 0.021 Uiso 1 1 calc R U . . .
H17B H 0.2131 0.0929 0.0669 0.021 Uiso 1 1 calc R U . . .
C18 C 0.4980(2) 0.24081(12) 0.13365(10) 0.0167(3) Uani 1 1 d . . . . .
C19 C 0.6124(2) 0.20238(12) 0.04192(10) 0.0210(3) Uani 1 1 d . . . . .
H19A H 0.4931 0.1552 -0.0256 0.031 Uiso 1 1 calc R U . . .
H19B H 0.7197 0.1506 0.0543 0.031 Uiso 1 1 calc R U . . .
H19C H 0.6980 0.2766 0.0380 0.031 Uiso 1 1 calc R U . . .
C20 C 0.1355(2) 0.27827(14) 0.44188(11) 0.0245(3) Uani 1 1 d . . . . .
H20A H 0.1569 0.3559 0.4306 0.037 Uiso 1 1 calc R U . . .
H20B H 0.1014 0.2935 0.5112 0.037 Uiso 1 1 calc R U . . .
H20C H 0.0062 0.2169 0.3846 0.037 Uiso 1 1 calc R U . . .
C21 C 0.5484(2) 0.32142(13) 0.53971(10) 0.0241(3) Uani 1 1 d . . . . .
H21A H 0.6961 0.2962 0.5379 0.036 Uiso 1 1 calc R U . . .
H21B H 0.5074 0.3220 0.6050 0.036 Uiso 1 1 calc R U . . .
H21C H 0.5631 0.4047 0.5391 0.036 Uiso 1 1 calc R U . . .
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
C5 O2 C18 117.68(9) . . ?
O1 C1 C6 120.96(11) . . ?
O1 C1 C2 120.66(12) . . ?
C6 C1 C2 118.37(11) . . ?
C1 C2 C3 112.71(11) . . ?
C4 C3 C2 110.71(10) . . ?
C5 C4 C3 111.82(10) . . ?
O2 C5 C6 124.51(11) . . ?
O2 C5 C4 111.48(10) . . ?
C6 C5 C4 124.01(11) . . ?
C5 C6 C1 120.04(11) . . ?
C5 C6 C7 121.59(11) . . ?
C1 C6 C7 118.33(11) . . ?
C6 C7 C8 110.71(10) . . ?
C9 C8 C18 113.10(10) . . ?
C9 C8 C7 110.73(10) . . ?
C18 C8 C7 110.74(10) . . ?
C8 C9 C10 112.24(10) . . ?
C9 C10 C16 105.57(9) . . ?
C9 C10 C11 114.17(10) . . ?
C16 C10 C11 115.82(10) . . ?
C20 C11 C21 107.57(11) . . ?
C20 C11 C12 110.82(11) . . ?
C21 C11 C12 104.79(10) . . ?
C20 C11 C10 112.31(10) . . ?
C21 C11 C10 110.18(10) . . ?
C12 C11 C10 110.85(10) . . ?
C13 C12 C11 119.16(11) . . ?
C12 C13 C14 115.28(12) . . ?
C15 C14 C13 109.01(11) . . ?
O3 C15 C14 120.66(12) . . ?
O3 C15 C16 120.37(11) . . ?
C14 C15 C16 118.96(11) . . ?
C15 C16 C17 107.07(10) . . ?
C15 C16 C10 116.54(10) . . ?
C17 C16 C10 110.24(10) . . ?
C18 C17 C16 113.49(10) . . ?
O2 C18 C19 107.32(9) . . ?
O2 C18 C17 104.88(9) . . ?
C19 C18 C17 110.37(10) . . ?
O2 C18 C8 110.44(10) . . ?
C19 C18 C8 112.46(10) . . ?
C17 C18 C8 111.04(10) . . ?
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 C1 1.2264(16) . ?
O2 C5 1.3500(15) . ?
O2 C18 1.4757(14) . ?
O3 C15 1.2165(16) . ?
C1 C6 1.4633(18) . ?
C1 C2 1.5162(17) . ?
C2 C3 1.5236(19) . ?
C3 C4 1.5225(18) . ?
C4 C5 1.5043(17) . ?
C5 C6 1.3510(18) . ?
C6 C7 1.5066(17) . ?
C7 C8 1.5313(17) . ?
C8 C9 1.5287(16) . ?
C8 C18 1.5295(17) . ?
C9 C10 1.5348(17) . ?
C10 C16 1.5469(16) . ?
C10 C11 1.5642(16) . ?
C11 C20 1.5285(18) . ?
C11 C21 1.5417(18) . ?
C11 C12 1.5490(18) . ?
C12 C13 1.525(2) . ?
C13 C14 1.542(2) . ?
C14 C15 1.5083(18) . ?
C15 C16 1.5132(18) . ?
C16 C17 1.5435(17) . ?
C17 C18 1.5255(18) . ?
C18 C19 1.5215(17) . ?
