Myrcaulones A–C, Unusual Rearranged Triketone–Terpene Adducts from Myrciaria cauliflora
Chen, Ming; Wang, Wen-Jing; Li, Ni-Ping; Zeng, Hu-Hu; Guo, Hong; Jiang, Ren-Wang; Wang, Lei; Ye, Wen-Cai; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00283

data_1558661
_publ_section_title
;
 Myrcaulones A--C, Unusual Rearranged Triketone--Terpene Adducts from
 Myrciaria cauliflora
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00283
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H34 O4'
_chemical_formula_sum            'C23 H34 O4'
_chemical_formula_weight         374.50
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                110.288(11)
_cell_angle_beta                 110.241(13)
_cell_angle_gamma                91.134(13)
_cell_formula_units_Z            3
_cell_length_a                   10.715(2)
_cell_length_b                   11.6367(16)
_cell_length_c                   14.6771(16)
_cell_measurement_reflns_used    3249
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      73.6170
_cell_measurement_theta_min      3.4360
_cell_volume                     1590.1(5)
_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_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Rigaku Oxford SuperNova'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.1178
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6170
_diffrn_reflns_point_group_measured_fraction_full 0.591
_diffrn_reflns_point_group_measured_fraction_max 0.591
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         5.559
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49365
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             613.8875
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         6170
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.216
_refine_ls_R_factor_all          0.1496
_refine_ls_R_factor_gt           0.1277
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3099
_refine_ls_wR_factor_ref         0.3520
_reflns_Friedel_coverage         0.227
_reflns_Friedel_fraction_full    0.219
_reflns_Friedel_fraction_max     0.219
_reflns_number_gt                4669
_reflns_number_total             6170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00283_si_003.cif
_cod_data_source_block           w1
_cod_original_cell_volume        1590.1(4)
_cod_database_code               1558661
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.731(10)
 0.269(10)
2. 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
3.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C6'(H6'), C7'(H7'), C2A(H2A), C4A(H4A), C6B(H6BA), C7B(H7BA),
 C2C(H2C), C4C(H4C), C6D(H6D), C7D(H7D)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C4'(H4'A,H4'B), C9'(H9'A,
 H9'B), C3A(H3AA,H3AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB),
 C4B(H4BA,H4BB), C9B(H9BA,H9BB), C3C(H3CA,H3CB), C5C(H5CA,H5CB), C6C(H6CA,H6CB),
  C7C(H7CA,H7CB), C4D(H4DA,H4DB), C9D(H9DA,H9DB)
3.c Me refined with riding coordinates:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C8'(H8'A,H8'B,H8'C), C11'(H11A,H11B,
 H11C), C12'(H12A,H12B,H12C), C13'(H13A,H13B,H13C), C9A(H9AA,H9AB,H9AC),
 C10A(H10D,H10E,H10F), C8B(H8BA,H8BB,H8BC), C11B(H11D,H11E,H11F), C12B(H12D,
 H12E,H12F), C13B(H13D,H13E,H13F), C9C(H9CA,H9CB,H9CC), C10C(H10G,H10H,H10I),
 C8D(H8DA,H8DB,H8DC), C11D(H11G,H11H,H11I), C12D(H12G,H12H,H12I), C13D(H13G,
 H13H,H13I)
;
_shelx_res_checksum              36836
_shelx_hkl_checksum              64284
_olex2_submission_special_instructions 'No special instructions were received'