Guajavadimer A, a Dimeric Caryophyllene-Derived Meroterpenoid with a New Carbon Skeleton from the Leaves of Psidium guajava.
Li, Chuang-Jun; Ma, Jie; Sun, Hua; Zhang, Dan; Zhang, Dong-Ming; Organic letters 18 (2016) 168–171; doi:10.1021/acs.orglett.5b03117

data_1542383
_publ_section_title
;
 Guajavadimer A, a Dimeric Caryophyllene-Derived Meroterpenoid with a New
 Carbon Skeleton from the Leaves of Psidium guajava.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              168
_journal_page_last               171
_journal_paper_doi               10.1021/acs.orglett.5b03117
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C H Cl3, C61 H70 O8'
_chemical_formula_sum            'C62 H71 Cl3 O8'
_chemical_formula_weight         1050.54
_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             2015-10-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3434(4)
_cell_length_b                   17.0470(8)
_cell_length_c                   30.5673(13)
_cell_measurement_reflns_used    7957
_cell_measurement_temperature    100.9
_cell_measurement_theta_max      71.0633
_cell_measurement_theta_min      2.9650
_cell_volume                     5389.7(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.9
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -54.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -120.0000 60

  2 omega  -39.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000  -60.0000 27

  3 omega   10.00   37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   45.0000  -90.0000 27

  4 omega   18.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  120.0000 88

  5 omega    3.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -92.0000   -5.0000 26

  6 omega  -27.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  150.0000 82

  7 omega  -32.00   48.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -60.0000 80

  8 omega   63.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 34

  9 omega   39.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   30.0000 138

 10 omega   46.00   73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 27

 11 omega   45.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 39

 12 omega   42.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 48

 13 omega  102.00  128.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 26

 14 omega   40.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 35

 15 omega   56.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000  150.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1050606000
_diffrn_orient_matrix_UB_12      -0.0365220000
_diffrn_orient_matrix_UB_13      -0.0293426000
_diffrn_orient_matrix_UB_21      0.0304683000
_diffrn_orient_matrix_UB_22      0.0605695000
_diffrn_orient_matrix_UB_23      -0.0358727000
_diffrn_orient_matrix_UB_31      0.1012038000
_diffrn_orient_matrix_UB_32      -0.0562629000
_diffrn_orient_matrix_UB_33      -0.0196309000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            19407
_diffrn_reflns_theta_full        71.23
_diffrn_reflns_theta_max         71.23
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     668
_refine_ls_number_reflns         10218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+2.0043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                9595
_reflns_number_total             10218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03117_si_001.cif
_cod_data_source_block           exp_2551
_cod_original_cell_volume        5389.8(4)
_cod_database_code               1542383
_reflns_odcompleteness_completeness 99.91
_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.a Ternary CH refined with riding coordinates:
 C1"'(H1"'), C5A(H5A), C7(H7), C1A(H1A), C9(H9), C9B(H9B), C5B(H5B), C9A(H9A),
 C1B(H1B), C2'(H2')
2.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C6B(H6BA,H6BB), C7A(H7AA,H7AB), C10A(H10A,H10B), C3A(H3AA,
 H3AB), C2A(H2AA,H2AB), C10B(H10C,H10D), C3'(H3'A,H3'B), C3B(H3BA,H3BB),
 C7B(H7BA,H7BB), C2B(H2BA,H2BB)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8A), C15(H15), C14(H14), C16'(H16'), C13(H13), C11(H11),
 C14'(H14'), C15'(H15'), C12'(H12'), C13'(H13')
2.d X=CH2 refined with riding coordinates:
 C12A(H12A,H12B), C12B(H12C,H12D)
2.e Idealised Me refined as rotating group:
 C17'(H17A,H17B,H17C), C14B(H14A,H14B,H14C), C15B(H15A,H15B,H15C), C13B(H13A,
 H13B,H13C), C15A(H15D,H15E,H15F), C14A(H14D,H14E,H14F), C13A(H13D,H13E,H13F)
2.f Idealised tetrahedral OH refined as rotating group:
 O8(H8), O5(H5), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'