New sesquiterpenoids from the rhizomes of Acorus tatarinowii
Feng, Xiao-lin; Yu, Yang; Gao, Hao; Mu, Zhen-qiang; Cheng, Xiao-rui; Zhou, Wen-xia; Yao, Xin-sheng; RSC Advances  (2014) –; doi:10.1039/C4RA06481J

data_7217794
_publ_section_title
;
 New sesquiterpenoids from the rhizomes of Acorus tatarinowii
;
_journal_name_full               'RSC Advances'
_journal_paper_doi               10.1039/C4RA06481J
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         230.29
_chemical_name_common            4-epi-2-hydroxyacorenone
_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             2014-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   8.45530(10)
_cell_length_b                   19.4162(2)
_cell_length_c                   25.3236(2)
_cell_measurement_reflns_used    19497
_cell_measurement_temperature    155.5
_cell_measurement_theta_max      62.7015
_cell_measurement_theta_min      3.4878
_cell_volume                     4157.37(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_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-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      155.5
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega  -55.00   20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184   48.0000  -57.0000 75

  2 omega   76.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000 -180.0000 30

  3 omega    8.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000  150.0000 97

  4 omega   20.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 26

  5 omega   22.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  120.0000 47

  6 omega   33.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -120.0000 31

  7 omega   80.00  163.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  120.0000 83

  8 omega  100.00  160.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000   90.0000 60

  9 omega   19.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   60.0000 27

 10 omega   81.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  150.0000 52

 11 omega   23.00  116.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -80.0000   36.0000 93

 12 omega   19.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   90.0000 47

 13 omega  -77.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  103.0000   68.0000 77

 14 omega    8.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000   60.0000 98

 15 omega    3.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000  -60.0000 100

 16 omega   67.00  162.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   90.0000 95

 17 omega   37.00  164.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000  -60.0000 127

 18 omega   20.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -80.0000 -159.0000 102

 19 omega   60.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 101

 20 omega   60.00  161.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 101

 21 omega   67.00  162.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   30.0000 95

 22 omega  -49.00   -2.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  -80.0000 -143.0000 47

 23 omega  -37.00   12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -77.0000  150.0000 49

 24 omega    3.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000 -180.0000 100
;
_diffrn_measurement_device_type  'Gemini S ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0704946000
_diffrn_orient_matrix_UB_12      -0.0087713000
_diffrn_orient_matrix_UB_13      -0.0557394000
_diffrn_orient_matrix_UB_21      -0.0806263000
_diffrn_orient_matrix_UB_22      0.0673116000
_diffrn_orient_matrix_UB_23      -0.0176088000
_diffrn_orient_matrix_UB_31      0.1472619000
_diffrn_orient_matrix_UB_32      0.0410772000
_diffrn_orient_matrix_UB_33      0.0169921000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32665
_diffrn_reflns_theta_full        62.79
_diffrn_reflns_theta_max         62.79
_diffrn_reflns_theta_min         3.49
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
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    1.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0441P)^2^+0.5224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0756
_reflns_number_gt                6446
_reflns_number_total             6625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra06481j2.cif
_cod_data_source_block           4_Epi_2_hydroxyacorenone
_cod_depositor_comments
;

2017-03-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '3(C15 H24 O2)'
_cod_original_formula_sum        'C45 H54 O6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     690.88
_cod_database_code               7217794
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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:
 C1A(H1AA), C1B(H1BA), C4C(H4C), C4B(H4B), C11A(H11A), C2A(H2A), C2B(H2B),
 C11B(H11B), C4A(H4A), C11C(H11C), C1C(H1CA), C2C(H2C)
2.b Secondary CH2 refined with riding coordinates:
 C6B(H6BA,H6BB), C3A(H3AA,H3AB), C6A(H6AA,H6AB), C10C(H10E,H10F), C6C(H6CA,
 H6CB), C10A(H10A,H10B), C3B(H3BA,H3BB), C3C(H3CA,H3CB), C10B(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C9A(H9A), C9C(H9C), C9B(H9B)
2.d Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C14C(H14G,H14H,H14I), C13C(H13G,H13H,H13I), C12C(H12G,
 H12H,H12I), C12A(H12A,H12B,H12C), C14A(H14A,H14B,H14C), C12B(H12D,H12E,H12F),
 C13B(H13D,H13E,H13F), C14B(H14D,H14E,H14F), C15C(H15G,H15H,H15I), C15B(H15D,
 H15E,H15F), C15A(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B), O1C(H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'