Euphnerins A and B, Diterpenoids with a 5/6/6 Rearranged Spirocyclic Carbon Skeleton from the Stems of <i>Euphorbia neriifolia</i>.
Du, Min; An, Lijun; Xu, Jing; Guo, Yuanqiang; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.0c00249

data_1558897
_publ_section_title
;
 Euphnerins A and B, Diterpenoids with a 5/6/6 Rearranged Spirocyclic
 Carbon Skeleton from the Stems of <i>Euphorbia neriifolia</i>.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00249
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H32 O3, H2 O'
_chemical_formula_sum            'C20 H34 O4'
_chemical_formula_weight         338.47
_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   mixed
_audit_creation_date             2019-10-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.48738(6)
_cell_length_b                   8.60757(6)
_cell_length_c                   25.91521(18)
_cell_measurement_reflns_used    14779
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2210
_cell_measurement_theta_min      3.4160
_cell_volume                     1893.25(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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     -6.00  40.00   0.50    0.50    --    0.00 -77.00  60.00   92
  2  \w    -21.00   6.00   0.50    0.50    --    0.00  38.00  90.00   54
  3  \w     34.00  85.00   0.50    0.50    --    0.00  38.00  90.00  102
  4  \w    -65.00 -34.00   0.50    0.50    --    0.00 -77.00  60.00   62
  5  \w    -36.00  69.00   0.50    0.50    --    0.00  57.00-120.00  210
  6  \w      9.00 174.00   0.50    0.50    --   98.20   0.00-180.00  330
  7  \w      9.00 141.00   0.50    0.50    --   98.20 -82.00-120.00  264
  8  \w      9.00 135.00   0.50    0.50    --   98.20 -61.00-120.00  252
  9  \w     27.00  52.00   0.50    0.50    --   98.20 -82.00 -30.00   50
 10  \w    120.00 163.00   0.50    0.50    --   98.20  61.00-150.00   86
 11  \w     81.00 108.00   0.50    0.50    --   98.20 -82.00 -30.00   54
 12  \w     58.00 123.00   0.50    0.50    --   98.20  77.00  30.00  130
 13  \w    122.00 183.00   0.50    0.50    --   98.20  45.00   0.00  122
 14  \w     60.00 187.00   0.50    0.50    --   98.20  45.00-120.00  254
 15  \w     93.00 128.00   0.50    0.50    --   98.20 -30.00 -90.00   70
 16  \w     58.00 133.00   0.50    0.50    --   98.20  77.00   0.00  150
 17  \w     14.00  43.00   0.50    0.50    --   98.20 -30.00 -90.00   58
 18  \w     58.00 128.00   0.50    0.50    --   98.20  77.00  60.00  140
 19  \w     19.00  79.00   0.50    0.50    --   98.20 -77.00  30.00  120
 20  \w     17.00 139.00   0.50    0.50    --   98.20 -77.00  60.00  244
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137469000
_diffrn_orient_matrix_UB_12      -0.0671061000
_diffrn_orient_matrix_UB_13      -0.0548891000
_diffrn_orient_matrix_UB_21      0.1664669000
_diffrn_orient_matrix_UB_22      0.0605697000
_diffrn_orient_matrix_UB_23      -0.0125972000
_diffrn_orient_matrix_UB_31      0.0712059000
_diffrn_orient_matrix_UB_32      -0.1544834000
_diffrn_orient_matrix_UB_33      0.0189578000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18905
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.560
_diffrn_reflns_theta_min         3.411
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0410P)^2^+0.3186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3736
_reflns_number_total             3781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00249_si_002.cif
_cod_data_source_block           dm-2
_cod_original_cell_volume        1893.26(2)
_cod_database_code               1558897
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.851
_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, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O4(H4A,H4B)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3), C10(H10)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C16(H16A,H16B),
 C17(H17A,H17B)
2.d Aromatic/amide H refined with riding coordinates:
 C19(H19)
2.e X=CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.f Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C)
2.g Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.690