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_1549010
_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         '2(C20 H30 O4), C H4 O'
_chemical_formula_sum            'C41 H64 O9'
_chemical_formula_weight         700.92
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   7.8136(4)
_cell_length_b                   22.8068(11)
_cell_length_c                   65.613(5)
_cell_measurement_reflns_used    14136
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.2
_cell_measurement_theta_min      2.7
_cell_volume                     11692.4(12)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 600.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 35
               Slice: 23.0000 - 198.0000
         Image width: 5.0000
            Exp time: 600.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 600.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 31
               Slice: 42.0000 - 197.0000
         Image width: 5.0000
            Exp time: 600.0000
       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      -0.073159
_diffrn_orient_matrix_UB_12      0.007096
_diffrn_orient_matrix_UB_13      0.012260
_diffrn_orient_matrix_UB_21      -0.093406
_diffrn_orient_matrix_UB_22      0.015245
_diffrn_orient_matrix_UB_23      -0.008971
_diffrn_orient_matrix_UB_31      -0.047984
_diffrn_orient_matrix_UB_32      -0.040494
_diffrn_orient_matrix_UB_33      -0.001229
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.1391
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       76
_diffrn_reflns_limit_l_min       -77
_diffrn_reflns_number            50476
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.347
_diffrn_reflns_theta_min         2.694
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             4587
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(16)
_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     713
_refine_ls_number_reflns         11178
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1997
_refine_ls_R_factor_gt           0.0795
_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^)+(0.0695P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1907
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                4078
_reflns_number_total             11178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01025_si_005.cif
_cod_data_source_block           shelxl
_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_original_cell_volume        11692.5(12)
_cod_database_code               1549010
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.895
_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
 O28, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: O28(0.5) H28(0.5) C27(0.5) H27A(0.5) H27B(0.5) H27C(0.5)
4.a Ternary CH refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C9A(H9A), C11A(H11A), C12A(H12A), C2B(H2B),
 C3B(H3B), C5B(H5B), C9B(H9B), C11B(H11B), C12B(H12B), C2(H2), C3(H3), C5(H5),
 C9(H9), C11(H11), C12(H12)
4.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C1B(H1BA,H1BB), C7B(H7BA,
 H7BB), C8B(H8BA,H8BB), C1(H1A,H1B), C7(H7A,H7B), C8(H8A,H8B)
4.c Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C17A(H17A,H17B,H17C), C18A(H18A,H18B,H18C), C19A(H19A,
 H19B,H19C), C20A(H20A,H20B,H20C), C16B(H16D,H16E,H16F), C17B(H17D,H17E,H17F),
 C18B(H18D,H18E,H18F), C19B(H19D,H19E,H19F), C20B(H20D,H20E,H20F), C16(H16G,
 H16H,H16I), C17(H17G,H17H,H17I), C18(H18G,H18H,H18I), C19(H19G,H19H,H19I),
 C20(H20G,H20H,H20I), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
4.d Idealised tetrahedral OH refined as rotating group:
 O21A(H21A), O22A(H22A), O24A(H24A), O21B(H21B), O22B(H22B), O24B(H24B),
 O21(H21), O22(H22), O24(H24), O26(H26), O28(H28)
;
_shelx_res_checksum              72397
_shelx_hkl_checksum              8963
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'