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_1547840
_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_absolute_configuration unk
_chemical_formula_moiety         'C16 H22 O4'
_chemical_formula_sum            'C16 H22 O4'
_chemical_formula_weight         278.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0021(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.01771(12)
_cell_length_b                   6.66052(7)
_cell_length_c                   18.21093(19)
_cell_measurement_reflns_used    20910
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      76.4010
_cell_measurement_theta_min      3.6950
_cell_volume                     1443.49(3)
_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      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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   -118.00  -9.00   1.00    1.00    --  -41.49 -77.00  90.00  109
  2  \w    -66.00  33.00   1.00    1.00    --  -41.49  38.00-120.00   99
  3  \w      1.00  82.00   1.00    1.00    --   41.49 -99.00-120.00   81
  4  \w     23.00  98.00   1.00    1.00    --   41.49-125.00-180.00   75
  5  \w     86.00 178.00   1.00    3.25    --  112.00  45.00-150.00   92
  6  \w    100.00 178.00   1.00    3.25    --  112.00 111.00-120.00   78
  7  \w     29.00 109.00   1.00    3.25    --  112.00 -94.00 -90.00   80
  8  \w     36.00 140.00   1.00    3.25    --  112.00 -30.00  30.00  104
  9  \w     36.00 140.00   1.00    3.25    --  112.00 -30.00-120.00  104
 10  \w     36.00 116.00   1.00    3.25    --  112.00-111.00  30.00   80
 11  \w    100.00 178.00   1.00    3.25    --  112.00 111.00-180.00   78
 12  \w   -115.00 -13.00   1.00    1.00    --  -41.49 -57.00-150.00  102
 13  \w     30.00  56.00   1.00    1.04    --   41.49-125.00 120.00   26
 14  \w     63.00  97.00   1.00    1.04    --   41.49  38.00 -90.00   34
 15  \w     11.00  36.00   1.00    1.04    --   46.00  84.00 -70.94   25
 16  \w     23.00  48.00   1.00    1.04    --   54.00  78.00 -23.79   25
 17  \w     21.00  46.00   1.00    1.04    --   54.00  79.00  26.69   25
 18  \w     33.00  71.00   1.00    1.04    --   66.00  77.00 -69.72   38
 19  \w     67.00 111.00   1.00    1.04    --   66.00  75.00 -58.21   44
 20  \w     79.00 131.00   1.00    2.97    --  112.00  77.00 -60.00   52
 21  \w     79.00 105.00   1.00    2.97    --  112.00  77.00   0.00   26
 22  \w    105.00 131.00   1.00    2.97    --  112.00  77.00-120.00   26
 23  \w     79.00 105.00   1.00    2.97    --  112.00  77.00 -30.00   26
 24  \w     84.00 113.00   1.00    2.97    --  112.00  61.00 -30.00   29
 25  \w     80.00 105.00   1.00    2.97    --  112.00  77.00 -90.00   25
 26  \w    138.00 169.00   1.00    2.97    --  112.00 111.00 -60.00   31
 27  \w     83.00 142.00   1.00    2.97    --  112.00  61.00   0.00   59
 28  \w     86.00 118.00   1.00    2.97    --  112.00  45.00   0.00   32
 29  \w     86.00 112.00   1.00    2.97    --  112.00  45.00 -60.00   26
 30  \w     83.00 109.00   1.00    2.97    --  112.00  61.00 -90.00   26
 31  \w     89.00 120.00   1.00    2.97    --  112.00  45.00  30.00   31
 32  \w     83.00 132.00   1.00    2.97    --  112.00  61.00  30.00   49
 33  \w     83.00 130.00   1.00    2.97    --  112.00  61.00 -60.00   47
 34  \w    -50.00 -17.00   1.00    1.04    --  -41.49 -38.00-120.00   33
 35  \w    -56.00 -19.00   1.00    1.04    --  -41.49 -38.00  60.00   37
 36  \w     25.00  81.00   1.00    1.04    --   41.49-125.00  60.00   56
 37  \w      5.00  30.00   1.00    1.04    --   42.00  89.00 167.12   25
 38  \w     21.00  66.00   1.00    1.04    --   54.00  77.00  79.30   45
 39  \w    103.00 129.00   1.00    1.04    --   54.00  77.00  79.30   26
 40  \w     26.00  56.00   1.00    1.04    --   58.00  74.00-123.61   30
 41  \w     30.00  56.00   1.00    1.04    --   62.00  75.00 157.69   26
 42  \w     32.00  71.00   1.00    1.04    --   62.00  66.00  18.38   39
 43  \w     31.00  64.00   1.00    1.04    --   62.00  75.00-175.14   33
 44  \w     34.00  67.00   1.00    1.04    --   66.00  77.00  84.76   33
 45  \w    110.00 136.00   1.00    1.04    --   66.00  77.00-154.48   26
 46  \w     33.00  66.00   1.00    1.04    --   66.00  77.00-154.48   33
 47  \w    113.00 142.00   1.00    1.04    --   66.00  77.00  84.76   29
 48  \w     39.00  78.00   1.00    1.04    --   70.00  70.00 135.37   39
 49  \w     98.00 144.00   1.00    1.04    --   70.00  70.00 135.37   46
 50  \w     91.00 142.00   1.00    2.97    --   78.00  76.00-108.72   51
 51  \w     46.00  74.00   1.00    2.97    --   78.00  76.00-108.72   28
 52  \w     53.00  83.00   1.00    2.97    --   82.00  64.00  45.77   30
 53  \w     79.00 133.00   1.00    2.97    --  112.00  77.00 150.00   54
 54  \w     62.00  88.00   1.00    2.97    --  112.00 178.00 -90.00   26
 55  \w     70.00 105.00   1.00    2.97    --  112.00 178.00 -60.00   35
 56  \w     79.00 105.00   1.00    2.97    --  112.00  77.00-120.00   26
 57  \w     59.00 115.00   1.00    2.97    --  112.00-111.00 120.00   56
 58  \w     79.00 154.00   1.00    2.97    --  112.00  77.00  60.00   75
 59  \w     79.00 107.00   1.00    2.97    --  112.00  77.00 120.00   28
 60  \w     79.00 105.00   1.00    2.97    --  112.00  77.00-150.00   26
 61  \w    121.00 146.00   1.00    2.97    --  112.00 178.00 -90.00   25
 62  \w    152.00 178.00   1.00    2.97    --  112.00  77.00  90.00   26
 63  \w     79.00 105.00   1.00    2.97    --  112.00  77.00-180.00   26
 64  \w     79.00 104.00   1.00    2.97    --  112.00  77.00  90.00   25
 65  \w    120.00 149.00   1.00    2.97    --  112.00  77.00  30.00   29
 66  \w     55.00 107.00   1.00    2.97    --  112.00-111.00-120.00   52
 67  \w     86.00 111.00   1.00    2.97    --  112.00  61.00 150.00   25
 68  \w     79.00 105.00   1.00    2.97    --  112.00  77.00  30.00   26
 69  \w     83.00 147.00   1.00    2.97    --  112.00  61.00 120.00   64
 70  \w    153.00 178.00   1.00    2.97    --  112.00  77.00 150.00   25
 71  \w     41.00  67.00   1.00    1.04    --   70.00  62.00  21.14   26
 72  \w     66.00  92.00   1.00    2.97    --   98.00  74.00 -61.00   26
 73  \w     39.00  64.00   1.00    1.04    --   70.00  69.00  47.45   25
 74  \w     68.00  94.00   1.00    2.97    --   98.00  71.00  47.50   26
 75  \w     55.00  80.00   1.00    2.97    --   86.00  71.00  22.92   25
 76  \w     49.00  76.00   1.00    2.97    --   82.00  77.00 -24.05   27
;
_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      0.0633937000
_diffrn_orient_matrix_UB_12      0.0827330000
_diffrn_orient_matrix_UB_13      0.0730941000
_diffrn_orient_matrix_UB_21      0.1128216000
_diffrn_orient_matrix_UB_22      -0.0393442000
_diffrn_orient_matrix_UB_23      -0.0285428000
_diffrn_orient_matrix_UB_31      -0.0038739000
_diffrn_orient_matrix_UB_32      0.2122724000
_diffrn_orient_matrix_UB_33      -0.0338421000
_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  0.0296
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29447
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.596
_diffrn_reflns_theta_min         3.714
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.68959
_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    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 2561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5952
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0416P)^2^+0.1977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.806
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                5801
_reflns_number_total             5952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00462_si_002.cif
_cod_data_source_block           exp_459
_cod_depositor_comments
'Adding full bibliography for 1547837--1547840.cif.'
_cod_database_code               1547840
_chemical_oxdiff_formula         C16H22O4
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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:
 C4(H4), C5(H5), C11(H11), C4'(H4'), C5'(H5'), C11'(H11')
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C12(H12A,H12B), C2'(H2'A,H2'B),
 C3'(H3'A,H3'B), C6'(H6'A,H6'B), C12'(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C9'(H9')
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C14'(H14D,H14E,
 H14F), C15'(H15D,H15E,H15F), C16'(H16D,H16E,H16F)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1'(H1')
;
_shelx_res_checksum              4529
_shelx_hkl_checksum              76384
_shelx_shelxl_version_number     2014/7
_ins_header
;
TITL exp_459 in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184  12.017709   6.660524  18.210932  90.0000  98.0021  90.0000
ZERR    4.00   0.000119   0.000069   0.000185   0.0000   0.0009   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H O
UNIT 64.00 88.00 16.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2016-09-26
_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 1.313
_oxdiff_exptl_absorpt_empirical_full_min 0.686