Abietane diterpenoids from Caryopteris incana (Thunb.) Miq.
Zhao, Sen-Miao; Chou, Gui-Xin; Yang, Qing-Shan; Wang, Wei; Zhou, Jian-Li; Organic & biomolecular chemistry 14 (2016) 3510–3520; doi:10.1039/c6ob00139d

data_7154998
_publ_section_title
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 Abietane diterpenoids from Caryopteris incana (Thunb.) Miq.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3510
_journal_page_last               3520
_journal_paper_doi               10.1039/c6ob00139d
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H26 O5'
_chemical_formula_sum            'C20 H26 O5'
_chemical_formula_weight         346.41
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/cc1j1s8m
_audit_creation_date             2015-04-13
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_audit_update_record
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2015-05-20 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
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_cell_angle_alpha                106.111(5)
_cell_angle_beta                 92.693(5)
_cell_angle_gamma                95.261(6)
_cell_formula_units_Z            4
_cell_length_a                   11.9342(11)
_cell_length_b                   12.3874(11)
_cell_length_c                   13.3401(13)
_cell_measurement_reflns_used    3570
_cell_measurement_temperature    130
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      3.46
_cell_volume                     1881.3(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.1004
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15264
_diffrn_reflns_point_group_measured_fraction_full 0.651
_diffrn_reflns_point_group_measured_fraction_max 0.654
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.498
_diffrn_reflns_theta_min         3.458
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1193 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.6404.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     920
_refine_ls_number_reflns         8863
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1452P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.2030
_reflns_Friedel_coverage         0.391
_reflns_Friedel_fraction_full    0.366
_reflns_Friedel_fraction_max     0.367
_reflns_number_gt                7369
_reflns_number_total             8863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob00139d2.cif
_cod_data_source_block           cu_dm14215_0m
_cod_depositor_comments
'Adding full bibliography for 7154996--7154998.cif.'
_cod_database_code               7154998
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.871
_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:
 C5B(H5BA), C11B(H11B), C14B(H14B), C5A(H5AA), C11A(H11A), C14A(H14A), C5(H5C),
  C11(H11), C14(H14), C5C(H5CB), C11C(H11C), C14C(H14C)
2.b Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C6B(H6BA,H6BB), C13B(H13A,
 H13B), C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C6A(H6AA,H6AB),
 C13A(H13C,H13D), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C13(H13E,
 H13F), C1C(H1CA,H1CB), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C6C(H6CA,H6CB),
 C13C(H13G,H13H)
2.c Tetrahedral OH refined with riding coordinates:
 O5(H5)
2.d Idealised Me refined as rotating group:
 C15B(H15A,H15B,H15C), C18B(H18A,H18B,H18C), C19B(H19A,H19B,H19C), C20B(H20A,
 H20B,H20C), C15A(H15D,H15E,H15F), C18A(H18D,H18E,H18F), C19A(H19D,H19E,H19F),
 C20A(H20D,H20E,H20F), C15(H15G,H15H,H15I), C18(H18G,H18H,H18I), C19(H19G,H19H,
 H19I), C20(H20G,H20H,H20I), C15C(H15J,H15K,H15L), C18C(H18J,H18K,H18L),
 C19C(H19J,H19K,H19L), C20C(H20J,H20K,H20L)
2.e Idealised tetrahedral OH refined as rotating group:
 O5B(H5B), O5A(H5A), O5C(H5CA)
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_shelx_res_checksum              94712
_olex2_submission_special_instructions 'No special instructions were received'