#------------------------------------------------------------------------------
#$Date: 2023-04-04 04:25:23 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282234 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/65/7246558.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_7246558
loop_
_publ_author_name
'Tseng, Hsuan-Jung'
'Kuo, Liang-Mou'
'Tsai, Yu-Chi'
'Hu, Hao-Chun'
'Chen, Po-Jen'
'Chien, Su-Ying'
'Sheu, Jyh-Horng'
'Sung, Ping-Jyun'
_publ_section_title
;
 Sinulariaone A: a novel diterpenoid with a 13-membered carbocyclic
 skeleton from an octocoral Sinularia species
;
_journal_issue                   15
_journal_name_full               'RSC Advances'
_journal_page_first              10408
_journal_page_last               10413
_journal_paper_doi               10.1039/D3RA01589K
_journal_volume                  13
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H32 O2'
_chemical_formula_weight         304.45
_chemical_name_systematic        sinulariaone
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-12-15 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0173(3)
_cell_length_b                   10.8659(3)
_cell_length_c                   18.6542(6)
_cell_measurement_reflns_used    8431
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.3640
_cell_measurement_theta_min      4.1400
_cell_volume                     1827.76(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         4.710
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.531
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.484
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
; 
 Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.264
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0601
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3095
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra01589k2.cif
_cod_data_source_block           ic21808
_cod_database_code               7246558
_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   0.741
_shelx_estimated_absorpt_t_max   0.930
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
O1 O 0.6436(3) 0.2552(2) 0.53923(14) 0.0303(6) Uani 1 1 d . . . . .
O2 O 0.9634(3) 0.5825(3) 0.26508(16) 0.0417(7) Uani 1 1 d . . . . .
C1 C 0.4973(4) 0.5544(3) 0.34973(19) 0.0249(7) Uani 1 1 d . . . . .
C2 C 0.6269(4) 0.5845(3) 0.31877(19) 0.0273(7) Uani 1 1 d . . . . .
H2A H 0.6248 0.6053 0.2693 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7757(4) 0.5881(3) 0.35611(19) 0.0252(7) Uani 1 1 d . . . . .
H3A H 0.7681 0.5392 0.4014 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8224(4) 0.7198(3) 0.3756(2) 0.0307(8) Uani 1 1 d . . . . .
H4A H 0.7340 0.7671 0.3909 0.037 Uiso 1 1 calc R U . . .
H4B H 0.8646 0.7607 0.3328 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9376(4) 0.7204(3) 0.4361(2) 0.0296(8) Uani 1 1 d . . . . .
H5A H 1.0215 0.6661 0.4230 0.036 Uiso 1 1 calc R U . . .
H5B H 0.9766 0.8049 0.4425 0.036 Uiso 1 1 calc R U . . .
C6 C 0.8698(4) 0.6767(3) 0.50527(19) 0.0272(7) Uani 1 1 d . . . . .
H6A H 0.7805 0.7166 0.5191 0.033 Uiso 1 1 calc R U . . .
C7 C 0.9179(4) 0.5896(3) 0.5498(2) 0.0275(7) Uani 1 1 d . . . . .
C8 C 0.8238(4) 0.5509(3) 0.61305(19) 0.0285(7) Uani 1 1 d . . . . .
H8A H 0.7311 0.5998 0.6129 0.034 Uiso 1 1 calc R U . . .
H8B H 0.8779 0.5704 0.6578 0.034 Uiso 1 1 calc R U . . .
C9 C 0.7835(4) 0.4126(3) 0.61314(19) 0.0290(7) Uani 1 1 d . . . . .
H9A H 0.8733 0.3635 0.6237 0.035 Uiso 1 1 calc R U . . .
H9B H 0.7099 0.3963 0.6514 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7203(4) 0.3730(3) 0.5419(2) 0.0264(7) Uani 1 1 d . . . . .
H10A H 0.7863 0.3895 0.4999 0.032 Uiso 1 1 calc R U . . .
C11 C 0.5614(4) 0.3682(3) 0.52456(19) 0.0266(7) Uani 1 1 d . . . . .
C12 C 0.5198(4) 0.3839(3) 0.44637(19) 0.0278(7) Uani 1 1 d . . . . .
H12A H 0.4303 0.3343 0.4358 0.033 Uiso 1 1 calc R U . . .
H12B H 0.6015 0.3531 0.4158 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4888(4) 0.5212(3) 0.42818(18) 0.0267(7) Uani 1 1 d . . . . .
H13A H 0.3885 0.5425 0.4459 0.032 Uiso 1 1 calc R U . . .
H13B H 0.5608 0.5727 0.4547 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3514(4) 0.5551(3) 0.3087(2) 0.0295(8) Uani 1 1 d . . . . .
H14A H 0.2758 0.5944 0.3405 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3540(5) 0.6278(4) 0.2399(2) 0.0415(10) Uani 1 1 d . . . . .
H15A H 0.2564 0.6236 0.2169 0.062 Uiso 1 1 calc R U . . .
H15B H 0.3784 0.7139 0.2504 0.062 Uiso 1 1 calc R U . . .
H15C H 0.4290 0.5933 0.2076 0.062 Uiso 1 1 calc R U . . .
C16 C 0.2994(5) 0.4235(4) 0.2945(3) 0.0467(11) Uani 1 1 d . . . . .
H16A H 0.2983 0.3774 0.3396 0.070 Uiso 1 1 calc R U . . .
H16B H 0.1993 0.4252 0.2740 0.070 Uiso 1 1 calc R U . . .
H16C H 0.3673 0.3837 0.2607 0.070 Uiso 1 1 calc R U . . .
C17 C 0.8882(4) 0.5249(3) 0.30677(19) 0.0282(7) Uani 1 1 d . . . . .
C18 C 0.8970(5) 0.3871(4) 0.3127(3) 0.0492(12) Uani 1 1 d . . . . .
H18A H 0.8274 0.3585 0.3494 0.074 Uiso 1 1 calc R U . . .
H18B H 0.8712 0.3500 0.2664 0.074 Uiso 1 1 calc R U . . .
H18C H 0.9980 0.3630 0.3260 0.074 Uiso 1 1 calc R U . . .
C19 C 1.0632(4) 0.5232(3) 0.5417(2) 0.0347(8) Uani 1 1 d . . . . .
H19A H 1.0744 0.4634 0.5806 0.052 Uiso 1 1 calc R U . . .
H19B H 1.0652 0.4801 0.4955 0.052 Uiso 1 1 calc R U . . .
H19C H 1.1447 0.5828 0.5435 0.052 Uiso 1 1 calc R U . . .
C20 C 0.4423(4) 0.3978(3) 0.5779(2) 0.0312(8) Uani 1 1 d . . . . .
H20A H 0.3930 0.4746 0.5641 0.047 Uiso 1 1 calc R U . . .
H20B H 0.3695 0.3308 0.5789 0.047 Uiso 1 1 calc R U . . .
H20C H 0.4865 0.4072 0.6256 0.047 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
C11 O1 C10 60.5(2) . . ?
C2 C1 C13 121.3(3) . . ?
C2 C1 C14 122.3(3) . . ?
C13 C1 C14 116.4(3) . . ?
C1 C2 C3 125.4(3) . . ?
C2 C3 C4 112.1(3) . . ?
C2 C3 C17 107.4(3) . . ?
C4 C3 C17 112.3(3) . . ?
C3 C4 C5 111.4(3) . . ?
C6 C5 C4 110.7(3) . . ?
C7 C6 C5 128.8(3) . . ?
C6 C7 C8 120.1(3) . . ?
C6 C7 C19 124.2(4) . . ?
C8 C7 C19 115.7(3) . . ?
C7 C8 C9 113.7(3) . . ?
C10 C9 C8 111.4(3) . . ?
O1 C10 C11 59.9(2) . . ?
O1 C10 C9 117.4(3) . . ?
C11 C10 C9 124.9(3) . . ?
O1 C11 C10 59.6(2) . . ?
O1 C11 C20 114.8(3) . . ?
C10 C11 C20 123.0(3) . . ?
O1 C11 C12 113.6(3) . . ?
C10 C11 C12 116.7(3) . . ?
C20 C11 C12 115.9(3) . . ?
C11 C12 C13 111.2(3) . . ?
C1 C13 C12 115.6(3) . . ?
C15 C14 C1 114.7(3) . . ?
C15 C14 C16 110.3(3) . . ?
C1 C14 C16 110.3(3) . . ?
O2 C17 C18 122.3(4) . . ?
O2 C17 C3 121.8(3) . . ?
C18 C17 C3 115.9(3) . . ?
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 C11 1.460(4) . ?
O1 C10 1.456(4) . ?
O2 C17 1.207(5) . ?
C1 C2 1.343(5) . ?
C1 C13 1.509(5) . ?
C1 C14 1.522(5) . ?
C2 C3 1.513(5) . ?
C3 C4 1.536(4) . ?
C3 C17 1.533(5) . ?
C4 C5 1.533(5) . ?
C5 C6 1.505(5) . ?
C6 C7 1.331(5) . ?
C7 C8 1.513(5) . ?
C7 C19 1.504(5) . ?
C8 C9 1.547(4) . ?
C9 C10 1.508(5) . ?
C10 C11 1.470(5) . ?
C11 C20 1.499(5) . ?
C11 C12 1.516(5) . ?
C12 C13 1.556(4) . ?
C14 C15 1.507(5) . ?
C14 C16 1.528(5) . ?
C17 C18 1.503(5) . ?
