Sarcoglaucins A-I, new antifouling cembrane-type diterpenes from the South China Sea soft coral Sarcophyton glaucum
Zhang, Jing; Tang, Xuli; Han, Xiao; Feng, Danqing; Luo, Xiangchao; Ofwegen, Leen van; Li, Pinglin; Li, Guoqiang; Organic Chemistry Frontiers 6 (2019) 2004–; doi:10.1039/C9QO00386J

data_1554901
_publ_section_title
;
 Sarcoglaucins A-I, new antifouling cembrane-type diterpenes from the
 South China Sea soft coral Sarcophyton glaucum
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2004
_journal_paper_doi               10.1039/C9QO00386J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C20 H30 O4'
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_weight         334.44
_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_date             2018-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2018-08-21 deposited with the CCDC.	2019-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9964(3)
_cell_length_b                   10.5385(3)
_cell_length_c                   17.4587(5)
_cell_measurement_reflns_used    2924
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.7070
_cell_measurement_theta_min      4.8830
_cell_volume                     1839.22(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -43.00  -2.00   1.00    1.00    --  -41.49 125.00   0.00   41
  2  \w    -70.00  32.00   1.00    1.00    --  -41.49  57.00-150.00  102
  3  \w     27.00  91.00   1.00    1.00    --   41.49-125.00 120.00   64
  4  \w     99.00 145.00   1.00    5.00    --  107.19 125.00   0.00   46
  5  \w     36.00 118.00   1.00    5.00    --  107.19-125.00 150.00   82
  6  \w     41.00 119.00   1.00    5.00    --  107.19 -45.00-120.00   78
  7  \w    107.00 177.00   1.00    5.00    --  107.19 125.00 -30.00   70
  8  \w     52.00 176.00   1.00    5.00    --  107.19   0.00-180.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1354123000
_diffrn_orient_matrix_UB_12      0.0496517000
_diffrn_orient_matrix_UB_13      0.0295422000
_diffrn_orient_matrix_UB_21      -0.0169026000
_diffrn_orient_matrix_UB_22      0.0786247000
_diffrn_orient_matrix_UB_23      -0.0737596000
_diffrn_orient_matrix_UB_31      -0.0713728000
_diffrn_orient_matrix_UB_32      -0.1129287000
_diffrn_orient_matrix_UB_33      -0.0383851000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.998
_diffrn_reflns_theta_min         4.902
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1277 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(16)
_refine_ls_extinction_coef       0.00070(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0365
_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/[\s^2^(Fo^2^)+(0.0332P)^2^+0.0648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3270
_reflns_number_total             3573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00386j2.cif
_cod_data_source_block           20180117e
_cod_database_code               1554901
_chemical_oxdiff_formula         C1H1O1
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C3(H3), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C8(H8A,H8B), C5(H5A,H5B), C4(H4A,H4B), C9(H9A,
 H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C7(H7)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C20(H20A,H20B,
 H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O19(H19)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.567
_oxdiff_exptl_absorpt_empirical_full_min 0.708