Structurally Diverse Diterpenoids from Sandwithia guyanensis
Remy, Simon; Olivon, Florent; Desrat, Sandy; Blanchard, Florent; Eparvier, Véronique; Leyssen, Pieter; Neyts, Johan; Roussi, Fanny; Touboul, David; Litaudon, Marc; Journal of Natural Products  (2018) –; doi:10.1021/acs.jnatprod.7b01025

data_1549009
_publ_section_title
;
 Structurally Diverse Diterpenoids from Sandwithia guyanensis
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.7b01025
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 O3, O'
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_weight         334.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.224(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2449(19)
_cell_length_b                   10.3812(14)
_cell_length_c                   14.7800(17)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    293
_cell_measurement_theta_max      65.4
_cell_measurement_theta_min      3.4
_cell_volume                     2029.0(5)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 RapidII
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details
;
scan:
    Number of images: 16
               Slice: 20.0000 - 185.0000
         Image width: 10.0000
            Exp time: 1200.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 18
               Slice: 20.0000 - 200.0000
         Image width: 10.0000
            Exp time: 1200.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 18
               Slice: 20.0000 - 200.0000
         Image width: 10.0000
            Exp time: 1200.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 12
               Slice: 20.0000 - 144.0000
         Image width: 10.0000
            Exp time: 1200.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 6
               Slice: 36.0000 - 102.0000
         Image width: 10.0000
            Exp time: 1200.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 6
               Slice: 35.0000 - 95.0000
         Image width: 10.0000
            Exp time: 1200.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
;
_diffrn_measurement_device
;
Crystal Goniometer
;
_diffrn_measurement_device_type
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.066546
_diffrn_orient_matrix_UB_12      -0.001178
_diffrn_orient_matrix_UB_13      0.028952
_diffrn_orient_matrix_UB_21      0.004870
_diffrn_orient_matrix_UB_22      -0.095571
_diffrn_orient_matrix_UB_23      0.006515
_diffrn_orient_matrix_UB_31      0.035844
_diffrn_orient_matrix_UB_32      0.010798
_diffrn_orient_matrix_UB_33      0.060827
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1059
_diffrn_reflns_av_unetI/netI     0.2245
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21132
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         73.973
_diffrn_reflns_theta_min         3.342
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_description       Prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         7502
_refine_ls_number_restraints     379
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.3268
_refine_ls_R_factor_gt           0.1103
_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^)+(0.1550P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2562
_refine_ls_wR_factor_ref         0.3781
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.886
_reflns_number_gt                1776
_reflns_number_total             7502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01025_si_006.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               1549009
_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. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17,
 C18, C19, C20, O1, O2, O3, C1', C2', C3', C4', C5', C6', C7', C8', C9', C10',
 C11', C12', C13', C14', C15', C16', C17', C18', C19', C20', O1', O2', O3'
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(O6)=1-FVAR(1)
 Sof(O5)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C9(H9), C11(H11), C13(H13), C15(H15), C4'(H4'), C9'(H9'), C11'(H11'),
 C13'(H13'), C15'(H15')
4.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C7(H7a,H7b), C8(H8a,H8b), C12(H12a,H12b), C5'(H5'a,H5'b),
 C7'(H7'a,H7'b), C8'(H8'a,H8'b), C12'(H12c,H12d)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C1'(H1')
4.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,
 H19c), C20(H20a,H20b,H20c), C16'(H16d,H16e,H16f), C17'(H17d,H17e,H17f),
 C18'(H18d,H18e,H18f), C19'(H19d,H19e,H19f), C20'(H20d,H20e,H20f)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2'(H2')
;
_shelx_res_checksum              69973
_shelx_hkl_checksum              12743
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'