Rearranged Phloroglucinol-Monoterpenoid Adducts from Callistemon rigidus
Cao, Jia-Qing; Tian, Hai-Yan; Li, Man-Mei; Zhang, Wei; Wang, Ying; Wang, Lei; Ye, Wen-Cai; Journal of Natural Products  (2017) –; doi:10.1021/acs.jnatprod.7b00606

data_1548513
_publ_section_title
;
 Rearranged Phloroglucinol-Monoterpenoid Adducts from Callistemon rigidus
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.7b00606
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H30 O5'
_chemical_formula_sum            'C22 H30 O5'
_chemical_formula_weight         374.46
_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
_audit_creation_date             2017-02-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                117.449(2)
_cell_angle_beta                 110.752(2)
_cell_angle_gamma                94.972(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3123(2)
_cell_length_b                   11.7835(2)
_cell_length_c                   11.8236(2)
_cell_measurement_reflns_used    23415
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8710
_cell_measurement_theta_min      4.4260
_cell_volume                     1026.64(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_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    -67.00  -9.00   1.00    1.00    --  -41.64  57.00 -30.00   58
  2  \w    -70.00  27.00   1.00    1.00    --  -41.64  57.00  90.00   97
  3  \w     65.00  93.00   1.00    1.00    --   41.64-125.00-120.00   28
  4  \w     31.00  64.00   1.00    1.00    --   41.64-125.00-120.00   33
  5  \w    104.00 140.00   1.00    3.09    --  107.79 -77.00-150.00   36
  6  \w     83.00 169.00   1.00    3.09    --  107.79  45.00-120.00   86
  7  \w    110.00 175.00   1.00    3.09    --  107.79 125.00-120.00   65
  8  \w    103.00 167.00   1.00    3.09    --  107.79 125.00 -60.00   64
  9  \w     97.00 173.00   1.00    3.09    --  107.79 125.00-180.00   76
 10  \w     80.00 129.00   1.00    3.09    --  107.79  61.00   0.00   49
 11  \w     36.00  96.00   1.00    3.09    --  107.79 -77.00-150.00   60
 12  \w    -43.00 -18.00   1.00    1.00    --  -41.89 -37.00  30.00   25
 13  \w   -111.00 -16.00   1.00    1.00    --  -41.89 -57.00 -60.00   95
 14  \w    -77.00 -46.00   1.00    1.00    --  -41.89 -37.00  30.00   31
 15  \w   -116.00 -21.00   1.00    1.00    --  -41.89 -37.00 150.00   95
 16  \w   -115.00 -82.00   1.00    1.00    --  -41.89 -37.00  30.00   33
 17  \w     23.00  69.00   1.00    1.00    --   41.89-125.00 -30.00   46
 18  \w     12.00  45.00   1.00    1.00    --   46.00  82.00  61.68   33
 19  \w     12.00  37.00   1.00    1.00    --   46.00  81.00 -13.50   25
 20  \w     16.00  41.00   1.00    1.00    --   50.00  81.00  11.50   25
 21  \w     17.00  42.00   1.00    1.00    --   50.00  79.00 176.47   25
 22  \w     20.00  45.00   1.00    1.00    --   54.00  81.00-142.28   25
 23  \w     21.00  46.00   1.00    1.00    --   54.00  79.00-107.84   25
 24  \w     71.00 112.00   1.00    1.00    --   58.00  77.00 113.99   41
 25  \w     26.00  66.00   1.00    1.00    --   58.00  77.00 113.99   40
 26  \w    105.00 131.00   1.00    1.00    --   62.00  75.00 157.12   26
 27  \w     30.00  56.00   1.00    1.00    --   62.00  75.00 -36.73   26
 28  \w     31.00  56.00   1.00    1.00    --   62.00  76.00  73.84   25
 29  \w     32.00  58.00   1.00    1.00    --   62.00  75.00 157.12   26
 30  \w     38.00  71.00   1.00    1.00    --   66.00  77.00 177.89   33
 31  \w     91.00 141.00   1.00    1.00    --   66.00  77.00 -13.56   50
 32  \w     36.00  64.00   1.00    1.00    --   66.00  77.00 -13.56   28
 33  \w     34.00  71.00   1.00    1.00    --   66.00  74.00 -84.74   37
 34  \w     34.00  69.00   1.00    1.00    --   66.00  77.00-123.44   35
 35  \w    111.00 141.00   1.00    1.00    --   66.00  74.00 -84.74   30
 36  \w     37.00  64.00   1.00    1.00    --   70.00  77.00  34.06   27
 37  \w     37.00  69.00   1.00    1.00    --   70.00  77.00  87.93   32
 38  \w     56.00  82.00   1.00    3.09    --  107.79-125.00 120.00   26
 39  \w     81.00 106.00   1.00    3.09    --  107.79  61.00 -90.00   25
 40  \w     76.00 144.00   1.00    3.09    --  107.79  77.00  60.00   68
 41  \w     79.00 172.00   1.00    3.09    --  107.79  61.00  30.00   93
 42  \w    139.00 178.00   1.00    3.09    --  107.79 125.00 120.00   39
 43  \w     81.00 133.00   1.00    3.09    --  107.79  61.00 -30.00   52
 44  \w     75.00 174.00   1.00    3.09    --  107.79  77.00 150.00   99
 45  \w    120.00 155.00   1.00    3.09    --  107.79  77.00   0.00   35
 46  \w     76.00 102.00   1.00    3.09    --  107.79  77.00   0.00   26
 47  \w     75.00 101.00   1.00    3.09    --  107.79  77.00  30.00   26
 48  \w     76.00 102.00   1.00    3.09    --  107.79  77.00 -30.00   26
 49  \w    117.00 176.00   1.00    3.09    --  107.79  77.00 -90.00   59
 50  \w     75.00 113.00   1.00    3.09    --  107.79  77.00 -90.00   38
 51  \w     25.00  73.00   1.00    3.09    --  107.79 -94.00 -60.00   48
 52  \w     80.00 106.00   1.00    3.09    --  107.79  61.00-120.00   26
 53  \w     79.00 110.00   1.00    3.09    --  107.79  61.00  90.00   31
 54  \w     75.00 163.00   1.00    3.09    --  107.79  77.00  90.00   88
 55  \w     84.00 110.00   1.00    3.09    --  107.79  61.00  60.00   26
 56  \w     75.00 138.00   1.00    3.09    --  107.79  77.00-180.00   63
 57  \w     79.00 104.00   1.00    3.09    --  107.79  61.00 150.00   25
 58  \w     90.00 122.00   1.00    3.09    --  107.79-125.00 -90.00   32
 59  \w     75.00 104.00   1.00    3.09    --  107.79  77.00 -60.00   29
 60  \w     75.00 167.00   1.00    3.09    --  107.79  77.00 120.00   92
 61  \w     93.00 120.00   1.00    3.09    --  107.79-125.00 120.00   27
 62  \w     81.00 140.00   1.00    3.09    --  107.79  61.00 -60.00   59
 63  \w     55.00  81.00   1.00    3.09    --   86.00  70.00-153.94   26
 64  \w   -122.00  -1.00   1.00    1.00    --  -41.89 -19.00  90.00  121
 65  \w   -118.00  -9.00   1.00    1.00    --  -41.89 -77.00 -60.00  109
 66  \w    -46.00 130.00   1.00    1.00    --   41.89   0.00-180.00  176
 67  \w    -46.00 130.00   1.00    1.00    --   41.89   0.00 -90.00  176
 68  \w     23.00  98.00   1.00    1.00    --   41.89-125.00-180.00   75
 69  \w    -46.00 130.00   1.00    1.00    --   41.89   0.00-120.00  176
 70  \w    -46.00 130.00   1.00    1.00    --   41.89   0.00 -60.00  176
 71  \w    -46.00 130.00   1.00    1.00    --   41.89   0.00 -30.00  176
 72  \w    -46.00 130.00   1.00    1.00    --   41.89   0.00-150.00  176
 73  \w     11.00  38.00   1.00    1.00    --   46.00  84.00 160.13   27
 74  \w     21.00  49.00   1.00    1.00    --   54.00  78.00  52.14   28
 75  \w     21.00  49.00   1.00    1.00    --   54.00  78.00 -35.53   28
 76  \w     29.00 138.00   1.00    1.00    --   62.00  77.00  32.54  109
 77  \w     30.00 137.00   1.00    1.00    --   62.00  75.00 -65.43  107
 78  \w     30.00 137.00   1.00    1.00    --   62.00  74.00-132.45  107
 79  \w     34.00 141.00   1.00    1.00    --   66.00  75.00   6.24  107
 80  \w     45.00 146.00   1.00    1.00    --   74.00  60.00  42.45  101
;
_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      -0.1580766000
_diffrn_orient_matrix_UB_12      -0.0732104000
_diffrn_orient_matrix_UB_13      -0.1391610000
_diffrn_orient_matrix_UB_21      -0.0001646000
_diffrn_orient_matrix_UB_22      0.1326997000
_diffrn_orient_matrix_UB_23      0.0043948000
_diffrn_orient_matrix_UB_31      0.0971232000
_diffrn_orient_matrix_UB_32      -0.0300241000
_diffrn_orient_matrix_UB_33      -0.0867428000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28222
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.038
_diffrn_reflns_theta_min         4.434
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 3431 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         7647
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0580P)^2^+0.1114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                7543
_reflns_number_total             7647
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00606_si_002.cif
_cod_data_source_block           1606074
_cod_original_cell_volume        1026.64(4)
_cod_database_code               1548513
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C12 H20 N2 O4'
_chemical_oxdiff_usercomment     CUB-10
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2'(H2'), C6(H6), C7(H7), C8'(H8'), C8A(H8AA), C13'(H13'), C14(H14), C15(H15),
  C16A(H16F), C19'(H19')
2.b Secondary CH2 refined with riding coordinates:
 C4'(H4'A,H4'B), C8(H8A,H8B), C15'(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C7'(H7'), C10(H10), C18'(H18')
2.d Idealised Me refined as rotating group:
 C3'(H3'A,H3'B,H3'C), C5'(H5'A,H5'B,H5'C), C6'(H6'A,H6'B,H6'C), C9'(H9'A,H9'B,
 H9'C), C10'(H10A,H10B,H10C), C11'(H11A,H11B,H11C), C14'(H14A,H14B,H14C),
 C16'(H16C,H16D,H16E), C17'(H17A,H17B,H17C), C20'(H20A,H20B,H20C), C21'(H21A,
 H21B,H21C), C22'(H22A,H22B,H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7A)
;
_shelx_res_checksum              58443
_shelx_hkl_checksum              9463
_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.581