Sarcomililate A, an Unusual Diterpenoid with Tricyclo[11.3.0.0<sup>2,16</sup>]hexadecane Carbon Skeleton, and Its Potential Biogenetic Precursors from the Hainan Soft Coral Sarcophyton mililatensis.
Yang, Min; Li, Xiao-Lu; Wang, Jian-Rong; Lei, Xinxiang; Tang, Wei; Li, Xu-Wen; Sun, Han; Guo, Yue-Wei; The Journal of organic chemistry 84 (2019) 2568–2576; doi:10.1021/acs.joc.8b03020

data_4033729
_publ_section_title
;
 Sarcomililate A, an Unusual Diterpenoid with
 Tricyclo[11.3.0.0<sup>2,16</sup>]hexadecane Carbon Skeleton, and Its
 Potential Biogenetic Precursors from the Hainan Soft Coral Sarcophyton
 mililatensis.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2568
_journal_page_last               2576
_journal_paper_doi               10.1021/acs.joc.8b03020
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H36 O4'
_chemical_formula_sum            'C22 H36 O4'
_chemical_formula_weight         364.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5866(5)
_cell_length_b                   24.3205(11)
_cell_length_c                   9.5513(4)
_cell_measurement_reflns_used    2626
_cell_measurement_temperature    205
_cell_measurement_theta_max      66.924
_cell_measurement_theta_min      9.290
_cell_volume                     2226.89(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      205
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20215
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        66.583
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         3.635
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1079 before and 0.0604 after correction. The Ratio of minimum to maximum transmission is 0.8250. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3551
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03020_si_002.cif
_cod_data_source_block           zz
_cod_database_code               4033729
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.855
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B), C10(H10A,H10B), C9(H9A,H9B), C6(H6A,H6B),
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C7(H7)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'