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_1547837
_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 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.6427(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.34029(10)
_cell_length_b                   10.58915(8)
_cell_length_c                   11.42721(11)
_cell_measurement_reflns_used    16553
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      76.4330
_cell_measurement_theta_min      5.7430
_cell_volume                     1333.51(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (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      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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   -115.00 -21.00   1.00    1.00    --  -41.49 -38.00 120.00   94
  2  \w     41.00  66.00   1.00    1.00    --   41.49 -38.00  90.00   25
  3  \w     32.00  96.00   1.00    1.00    --   41.49-125.00 150.00   64
  4  \w    -32.00  -7.00   1.00    1.00    --   41.49 -38.00  90.00   25
  5  \w      1.00  48.00   1.00    1.00    --   41.49 -99.00   0.00   47
  6  \w    105.00 144.00   1.00    1.24    --  112.00 -77.00  60.00   39
  7  \w     47.00 103.00   1.00    1.24    --  112.00 -94.00  90.00   56
  8  \w    110.00 168.00   1.00    1.24    --  112.00  45.00 150.00   58
  9  \w     87.00 173.00   1.00    1.24    --  112.00  45.00 120.00   86
 10  \w     37.00 113.00   1.00    1.24    --  112.00-111.00  30.00   76
 11  \w    122.00 173.00   1.00    1.24    --  112.00 111.00 150.00   51
 12  \w     87.00 177.00   1.00    1.24    --  112.00  61.00-150.00   90
 13  \w     40.00  96.00   1.00    1.24    --  112.00 -94.00 -60.00   56
 14  \w    114.00 155.00   1.00    1.24    --  112.00  93.00  69.00   41
 15  \w     46.00  72.00   1.00    1.24    --  112.00 -61.00-120.00   26
 16  \w     -1.00  24.00   1.00    1.00    --   38.00  95.00 129.14   25
 17  \w      2.00  27.00   1.00    1.00    --   38.00  89.00   0.20   25
 18  \w   -113.00 -13.00   1.00    1.00    --  -41.49 -57.00 -60.00  100
 19  \w   -109.00 -20.00   1.00    1.00    --  -41.49 -38.00  30.00   89
 20  \w     37.00  87.00   1.00    1.00    --   41.49-125.00 -30.00   50
 21  \w    -33.00  -4.00   1.00    1.00    --   41.49 -38.00 -30.00   29
 22  \w      7.00  65.00   1.00    1.00    --   41.49 -38.00 -30.00   58
 23  \w      6.00  31.00   1.00    1.00    --   42.00  88.00-144.05   25
 24  \w     12.00  37.00   1.00    1.00    --   46.00  83.00  43.74   25
 25  \w     11.00  38.00   1.00    1.00    --   46.00  84.00 126.54   27
 26  \w     20.00  45.00   1.00    1.00    --   54.00  81.00 -89.60   25
 27  \w     79.00 114.00   1.00    1.00    --   58.00  77.00-120.81   35
 28  \w     26.00  66.00   1.00    1.00    --   58.00  77.00-120.81   40
 29  \w     30.00  56.00   1.00    1.00    --   62.00  76.00  91.03   26
 30  \w     34.00  70.00   1.00    1.00    --   66.00  75.00 -45.90   36
 31  \w     36.00  69.00   1.00    1.00    --   66.00  72.00 -81.89   33
 32  \w    113.00 139.00   1.00    1.00    --   66.00  72.00 -81.89   26
 33  \w     99.00 141.00   1.00    1.00    --   66.00  75.00 -45.90   42
 34  \w     39.00  68.00   1.00    1.00    --   70.00  76.00 144.90   29
 35  \w     39.00  64.00   1.00    1.00    --   70.00  76.00 115.40   25
 36  \w     37.00  72.00   1.00    1.00    --   70.00  77.00-118.95   35
 37  \w     38.00  65.00   1.00    1.00    --   70.00  76.00-165.84   27
 38  \w    114.00 144.00   1.00    1.00    --   70.00  72.00   5.36   30
 39  \w     39.00  70.00   1.00    1.00    --   70.00  72.00   5.36   31
 40  \w    110.00 147.00   1.00    1.00    --   74.00  73.00  47.43   37
 41  \w     42.00  76.00   1.00    1.00    --   74.00  73.00  47.43   34
 42  \w     37.00  93.00   1.00    1.24    --  112.00 -77.00-150.00   56
 43  \w     83.00 164.00   1.00    1.24    --  112.00  61.00  60.00   81
 44  \w    145.00 176.00   1.00    1.24    --  112.00  77.00  90.00   31
 45  \w     79.00 105.00   1.00    1.24    --  112.00  77.00 120.00   26
 46  \w     83.00 110.00   1.00    1.24    --  112.00  61.00 150.00   27
 47  \w     84.00 117.00   1.00    1.24    --  112.00  61.00  90.00   33
 48  \w     79.00 105.00   1.00    1.24    --  112.00  77.00  90.00   26
 49  \w     83.00 151.00   1.00    1.24    --  112.00  61.00 -60.00   68
 50  \w    127.00 154.00   1.00    1.24    --  112.00  61.00-120.00   27
 51  \w    116.00 176.00   1.00    1.24    --  112.00  77.00-120.00   60
 52  \w     84.00 115.00   1.00    1.24    --  112.00  61.00-120.00   31
 53  \w     79.00 114.00   1.00    1.24    --  112.00  77.00-120.00   35
 54  \w    124.00 175.00   1.00    1.24    --  112.00  77.00 -60.00   51
 55  \w     79.00 176.00   1.00    1.24    --  112.00  77.00   0.00   97
 56  \w     80.00 107.00   1.00    1.24    --  112.00  77.00 -60.00   27
 57  \w    143.00 177.00   1.00    1.24    --  112.00  77.00  30.00   34
 58  \w     79.00 128.00   1.00    1.24    --  112.00  77.00  30.00   49
 59  \w     77.00 116.00   1.00    1.24    --  112.00-111.00-150.00   39
 60  \w     79.00 131.00   1.00    1.24    --  112.00  77.00 -90.00   52
 61  \w     83.00 132.00   1.00    1.24    --  112.00 -77.00 -60.00   49
 62  \w     84.00 110.00   1.00    1.24    --  112.00  61.00-180.00   26
 63  \w    153.00 178.00   1.00    1.24    --  112.00  77.00-150.00   25
 64  \w     80.00 107.00   1.00    1.24    --  112.00  77.00-150.00   27
 65  \w     79.00 106.00   1.00    1.24    --  112.00  77.00 150.00   27
 66  \w     80.00 162.00   1.00    1.24    --  112.00  77.00-180.00   82
 67  \w     88.00 116.00   1.00    1.24    --  112.00-111.00 -60.00   28
 68  \w    147.00 178.00   1.00    1.24    --  112.00  61.00 -30.00   31
 69  \w     84.00 109.00   1.00    1.24    --  112.00  61.00 120.00   25
 70  \w    153.00 178.00   1.00    1.24    --  112.00  77.00 -30.00   25
 71  \w     80.00 135.00   1.00    1.24    --  112.00  77.00 -30.00   55
 72  \w     85.00 112.00   1.00    1.24    --  112.00  61.00  30.00   27
 73  \w    131.00 165.00   1.00    1.24    --  112.00  61.00  30.00   34
 74  \w     84.00 111.00   1.00    1.24    --  112.00  61.00 -30.00   27
 75  \w     95.00 135.00   1.00    1.24    --  112.00 -61.00  30.00   40
 76  \w    119.00 145.00   1.00    1.24    --  112.00 -77.00-150.00   26
 77  \w     41.00  66.00   1.00    1.24    --  112.00 -61.00  30.00   25
 78  \w     79.00 106.00   1.00    1.24    --  112.00  77.00  60.00   27
 79  \w     85.00 177.00   1.00    1.24    --  112.00  61.00 -90.00   92
;
_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      0.0342480000
_diffrn_orient_matrix_UB_12      -0.1310408000
_diffrn_orient_matrix_UB_13      -0.0403792000
_diffrn_orient_matrix_UB_21      -0.1353916000
_diffrn_orient_matrix_UB_22      -0.0308553000
_diffrn_orient_matrix_UB_23      -0.0491820000
_diffrn_orient_matrix_UB_31      0.0056439000
_diffrn_orient_matrix_UB_32      0.0552036000
_diffrn_orient_matrix_UB_33      -0.1232920000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27083
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.617
_diffrn_reflns_theta_min         4.011
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.177
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.038
_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     158
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0517P)^2^+0.4652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2628
_reflns_number_total             2806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00462_si_002.cif
_cod_data_source_block           exp_460
_cod_depositor_comments
'Adding full bibliography for 1547837--1547840.cif.'
_cod_database_code               1547837
_chemical_oxdiff_formula         C15H24O2
_reflns_odcompleteness_completeness 99.97
_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)
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(H2), C9(H9), C10(H10)
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(H2a)
;
_shelx_shelxl_version_number     2014/7
_ins_header
;
TITL exp_460 in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184  11.340292  10.589149  11.427214  90.0000 103.6427  90.0000
ZERR    4.00   0.000103   0.000083   0.000114   0.0000   0.0009   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H O
UNIT 60.00 96.00 8.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2016-09-27
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.690