Isolation and Biomimetic Total Synthesis of Tomentodiones A-B, Terpenoid-conjugated Phloroglucinols from the Leaves of Rhodomyrtus tomentosa
Liu, Hong-Xin; Chen, Kai; Tang, Gui-Hua; Yuan, Yun-Fei; Tan, Haibo; Qiu, SX; RSC Adv.  (2016) –; doi:10.1039/C6RA08776K

data_7225212
_publ_section_title
;
 Isolation and Biomimetic Total Synthesis of Tomentodiones A-B,
 Terpenoid-conjugated Phloroglucinols from the Leaves of Rhodomyrtus
 tomentosa
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA08776K
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H47 O3'
_chemical_formula_sum            'C30 H47 O3'
_chemical_formula_weight         455.68
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2015-10-18 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0146(3)
_cell_length_b                   10.5472(2)
_cell_length_c                   26.3161(5)
_cell_measurement_reflns_used    8788
_cell_measurement_temperature    292.55(10)
_cell_measurement_theta_max      66.7460
_cell_measurement_theta_min      3.3250
_cell_volume                     2779.66(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.55(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -24.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6688  -38.0000   60.0000 91

  2 omega   23.00   51.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -30.0000 28

  3 omega   23.00   51.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   30.0000 28

  4 omega   19.00   76.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 57

  5 omega   51.00   84.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000    0.0000 33

  6 omega   71.00   96.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000  -90.0000 25

  7 omega   48.00   74.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000 -180.0000 26

  8 omega   27.00   68.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -120.0000 41

  9 omega   22.00   69.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -150.0000 47

 10 omega   21.00   46.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000  -90.0000 25

 11 omega   13.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6688 -126.0000   30.0000 84

 12 omega   21.00   90.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000  150.0000 69

 13 omega   21.00   75.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  150.0000 54

 14 omega   86.00  112.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000    0.0000 26

 15 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000  -60.0000 104

 16 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000   60.0000 104

 17 omega   11.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000 -180.0000 104

 18 omega   66.00  125.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   90.0000 59

 19 omega   66.00  168.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -150.0000 102

 20 omega   16.00   69.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   90.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1380049000
_diffrn_orient_matrix_UB_12      0.0490545000
_diffrn_orient_matrix_UB_13      0.0168527000
_diffrn_orient_matrix_UB_21      -0.0625325000
_diffrn_orient_matrix_UB_22      0.0546040000
_diffrn_orient_matrix_UB_23      0.0487777000
_diffrn_orient_matrix_UB_31      0.0263272000
_diffrn_orient_matrix_UB_32      -0.1263292000
_diffrn_orient_matrix_UB_33      0.0276402000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19027
_diffrn_reflns_theta_full        66.92
_diffrn_reflns_theta_max         66.92
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.6348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                4448
_reflns_number_total             4890
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra08776k2.cif
_cod_data_source_block           01148a
_cod_original_cell_volume        2779.66(10)
_cod_database_code               7225212
_chemical_oxdiff_formula         'C20 H20 O6'
_chemical_oxdiff_usercomment     'tn28 block colorless 0.42 0.39 0.33 150K'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C9(H9), C13(H13), C18(H18), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C21(H21A,H21B), C26(H26A,
 H26B), C28(H28A,H28B)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C25(H25A,H25B,
 H25C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C1(H1A,
 H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_olex2_submission_special_instructions 'No special instructions were received'