Aquilanols A and B, Macrocyclic Humulene-Type Sesquiterpenoids from the Agarwood of Aquilaria malaccensis.
Ma, Chi Thanh; Eom, Taeyong; Cho, Eunji; Wu, Bo; Kim, Tae Ryong; Oh, Ki Bong; Han, Sang Beom; Kwon, Sung Won; Park, Jeong Hill; Journal of natural products 80 (2017) 3043–3048; doi:10.1021/acs.jnatprod.7b00462

data_1547838
_publ_section_title
;
 Aquilanols A and B, Macrocyclic Humulene-Type Sesquiterpenoids from the
 Agarwood of Aquilaria malaccensis.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              3043
_journal_page_last               3048
_journal_paper_doi               10.1021/acs.jnatprod.7b00462
_journal_volume                  80
_journal_year                    2017
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.765(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6837(3)
_cell_length_b                   6.49484(20)
_cell_length_c                   18.4991(6)
_cell_measurement_reflns_used    3989
_cell_measurement_temperature    295.0(2)
_cell_measurement_theta_max      75.1440
_cell_measurement_theta_min      4.1390
_cell_volume                     1379.08(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.44a (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      295.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -66.00  33.00   1.00    2.50    --  -41.49  38.00 -60.00   99
  2  \w    -66.00  33.00   1.00    2.50    --  -41.49  38.00-150.00   99
  3  \w     23.00  98.00   1.00    2.50    --   41.49-125.00 -60.00   75
  4  \w     36.00 140.00   1.00   10.00    --  112.00 -30.00-180.00  104
  5  \w     29.00 109.00   1.00   10.00    --  112.00 -94.00   0.00   80
  6  \w     84.00 178.00   1.00   10.00    --  112.00  30.00   0.00   94
  7  \w     39.00 138.00   1.00   10.00    --  112.00 -45.00   0.00   99
  8  \w     36.00 116.00   1.00   10.00    --  112.00-111.00  90.00   80
  9  \w    100.00 178.00   1.00   10.00    --  112.00 111.00 -30.00   78
 10  \w     63.00 166.00   1.00   10.00    --  112.00  15.00 -60.00  103
 11  \w     78.00 116.00   1.00   10.00    --  112.00-111.00 120.00   38
 12  \w     87.00 114.00   1.00   10.00    --  112.00  45.00  30.00   27
 13  \w    116.00 143.00   1.00   10.00    --  112.00  45.00  30.00   27
 14  \w    147.00 174.00   1.00   10.00    --  112.00  45.00  30.00   27
 15  \w     73.00 139.00   1.00   10.00    --  112.00 -61.00  60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0964133000
_diffrn_orient_matrix_UB_12      0.0037393000
_diffrn_orient_matrix_UB_13      -0.0465466000
_diffrn_orient_matrix_UB_21      -0.0927969000
_diffrn_orient_matrix_UB_22      0.0254692000
_diffrn_orient_matrix_UB_23      -0.0703633000
_diffrn_orient_matrix_UB_31      0.0085344000
_diffrn_orient_matrix_UB_32      0.2359529000
_diffrn_orient_matrix_UB_33      0.0083908000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8922
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.378
_diffrn_reflns_theta_min         4.154
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.44a (Rigaku Oxford Diffraction, 2015)
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    1.215
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0572P)^2^+0.1918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2401
_reflns_number_total             2861
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00462_si_002.cif
_cod_data_source_block           exp_500
_cod_depositor_comments
'Adding full bibliography for 1547837--1547840.cif.'
_cod_original_cell_volume        1379.07(7)
_cod_database_code               1547838
_chemical_oxdiff_formula         C15H24O3
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C6(H6), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C4(H4a,H4b), C5(H5a,H5b), C8(H8a,H8b), C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2a)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c), C15(H15a,H15b,H15c)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-10-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.863