Anti-inflammatory Lathyrane Diterpenoids from Euphorbia lathyris.
Zhang, Cui-Yun; Wu, Yan-Li; Zhang, Peng; Chen, Zhuang-Zhuang; Li, Hua; Chen, Li-Xia; Journal of natural products 82 (2019) 756–764; doi:10.1021/acs.jnatprod.8b00600

data_1552636
_publ_section_title
;
 Anti-inflammatory Lathyrane Diterpenoids from Euphorbia lathyris.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              756
_journal_page_last               764
_journal_paper_doi               10.1021/acs.jnatprod.8b00600
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H38 O6'
_chemical_formula_sum            'C31 H38 O6'
_chemical_formula_weight         506.61
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.6550(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.13676(11)
_cell_length_b                   17.28546(14)
_cell_length_c                   33.1549(2)
_cell_measurement_reflns_used    35391
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4860
_cell_measurement_theta_min      2.6500
_cell_volume                     5797.54(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.974
_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   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00-120.00  100
  2  \w   -113.00 -14.00   1.00    1.00    --  -40.98 -51.00 -35.00   99
  3  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00-150.00  109
  4  \w     23.00  97.00   1.00    1.00    --   40.98-125.00-120.00   74
  5  \w    -35.00  74.00   1.00    1.00    --   40.98 -77.00  90.00  109
  6  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00 -60.00   81
  7  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-120.00  100
  8  \w     74.00 178.00   1.00    1.00    --  106.95  77.00-180.00  104
  9  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 150.00  104
 10  \w     74.00 178.00   1.00    1.00    --  106.95  77.00-150.00  104
 11  \w     81.00 178.00   1.00    1.00    --  106.95  45.00  60.00   97
 12  \w     79.00 178.00   1.00    1.00    --  106.95  30.00  30.00   99
 13  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-150.00  100
 14  \w     34.00 133.00   1.00    1.00    --  106.95 -45.00-180.00   99
 15  \w     78.00 154.00   1.00    1.00    --  106.95  61.00 -30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0967077000
_diffrn_orient_matrix_UB_12      -0.0441377000
_diffrn_orient_matrix_UB_13      0.0256649000
_diffrn_orient_matrix_UB_21      0.1175043000
_diffrn_orient_matrix_UB_22      -0.0331333000
_diffrn_orient_matrix_UB_23      0.0263030000
_diffrn_orient_matrix_UB_31      -0.0054493000
_diffrn_orient_matrix_UB_32      0.0699557000
_diffrn_orient_matrix_UB_33      0.0286106000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            49755
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.547
_diffrn_reflns_theta_min         2.671
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 9382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1389
_refine_ls_number_reflns         21881
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0584P)^2^+1.0575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                21343
_reflns_number_total             21881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00600_si_004.cif
_cod_data_source_block           zcy-009
_cod_original_cell_volume        5797.53(9)
_cod_database_code               1552636
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.921
_reflns_odcompleteness_completeness 99.24
_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. Rigid bond restraints
 C01R, O00M
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C03Y, C044
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C01R \\sim O00M: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
C03Y \\sim C044: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
4.a Ternary CH refined with riding coordinates:
 C00U(H00U), C00Z(H00Z), C015(H015), C016(H016), C018(H018), C5(H5),
 C01B(H01B), C01F(H01F), C01J(H01J), C01N(H01N), C01O(H01O), C01P(H01P),
 C01S(H01S), C01T(H01T), C01X(H01X), C021(H021), C024(H024), C02B(H02D), C4(H4),
  C11(H11), C02W(H02), C3(H3A), C9(H9), C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C01Z(H01A,H01E), C022(H02I,H02K), C02E(H02E,H02F), C02O(H02T,H02U), C02Q(H02R,
 H02S), C02T(H02Z,HB), C02U(H02G,H02H), C8(H8A,H8B), C7(H7A,H7B), C03A(H03,HC),
 C1(H1A,H1B), C03S(H03K,H03L)
4.c Aromatic/amide H refined with riding coordinates:
 C00Y(H00Y), C012(H012), C019(H019), C01C(H01C), C01D(H01D), C01G(H01G),
 C01K(H01K), C01U(H01U), C01V(H01V), C020(H020), C7'(H7'), C12(H12), C8'(H8'),
 C9'(H9'), C2'(H2'), C02J(H02J), C3'(H3'), C6'(H6'), C031(H031), C032(H032),
 C035(H035), C038(H038), C03C(H03R), C5'(H5'), C03G(H03G), C03I(H03I),
 C03R(H3AA), C03V(H03Z), C03Y(H5AA), C03Z(H6AA), C041(H041), C044(H044)
4.d Idealised Me refined as rotating group:
 C026(H02A,H02B,H02C), C029(H02L,H02M,H02N), C02A(H02O,H02P,H02Q), C02R(H02V,
 H02W,H02X), C02S(H02Y,H,HA), C03D(H03A,H03B,H03C), C03F(H03S,H03T,H03U),
 C03J(H03V,H03W,H03X), C03K(H1AA,HD,HE), C20(H20A,H20B,H20C), C03M(H2AA,HF,HG),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C03Q(H03F,H03H,H03J), C03U(H03Y,HH,
 HI), C03W(H03M,H03N,H03O), C03X(H4AA,HJ,HK), C16(H16A,H16B,H16C), C2"(H2"A,
 H2"B,H2"C), C045(H04A,H04B,H04C)
4.e Idealised tetrahedral OH refined as rotating group:
 O006(H006), O00A(H00A), O3(H3), O00I(H00I)
;
_olex2_date_sample_data_collection 2018-04-11
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.743