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_1548512
_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         'C21 H28 O5'
_chemical_formula_sum            'C21 H28 O5'
_chemical_formula_weight         360.43
_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             2017-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.1036(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   7.48087(9)
_cell_length_b                   22.1683(2)
_cell_length_c                   11.52385(13)
_cell_measurement_reflns_used    15550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6020
_cell_measurement_theta_min      3.8280
_cell_volume                     1911.09(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.970
_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    -82.00  39.00   1.00    1.00    --  -40.98  19.00 120.00  121
  2  \w     23.00  97.00   1.00    1.00    --   40.98-125.00  90.00   74
  3  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00-120.00   81
  4  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00-180.00   85
  5  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00  60.00   85
  6  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  30.00  100
  7  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-120.00   84
  8  \w     31.00 135.00   1.00    1.00    --  106.95 -30.00-150.00  104
  9  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 -30.00   85
 10  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -55.00-135.00  100
 11  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00   0.00  109
 12  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 120.00  100
 13  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -30.00  104
 14  \w     54.00 178.00   1.00    1.00    --  106.95  15.00-180.00  124
 15  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  60.00  104
 16  \w     54.00 178.00   1.00    1.00    --  106.95  15.00 -60.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0582878000
_diffrn_orient_matrix_UB_12      0.0651064000
_diffrn_orient_matrix_UB_13      -0.0274385000
_diffrn_orient_matrix_UB_21      -0.1234613000
_diffrn_orient_matrix_UB_22      0.0003673000
_diffrn_orient_matrix_UB_23      -0.1071750000
_diffrn_orient_matrix_UB_31      -0.1541530000
_diffrn_orient_matrix_UB_32      0.0243002000
_diffrn_orient_matrix_UB_33      0.0750624000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17634
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.665
_diffrn_reflns_theta_min         3.836
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       blocks
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 3189 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         7306
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0492
_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^+1.7610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                7206
_reflns_number_total             7306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00606_si_004.cif
_cod_data_source_block           CR_B_16
_cod_database_code               1548512
_shelx_shelxl_version_number     2016/4
_cell_oxdiff_angle_alpha         89.9892(17)
_cell_oxdiff_angle_beta          90.1281(18)
_cell_oxdiff_angle_gamma         90.0145(18)
_cell_oxdiff_length_a            7.48136(18)
_cell_oxdiff_length_b            22.1681(5)
_cell_oxdiff_length_c            11.5232(2)
_cell_oxdiff_measurement_reflns_used 15550
_cell_oxdiff_volume              1911.09(7)
_reflns_odcompleteness_completeness 99.23
_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:
 C6(H6), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17), C2'(H2'), C6'(H6'),
 C11'(H11'), C15'(H15'), C9A(H9A1), C18A(H18F)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C11(H11)
2.d Idealised Me refined as rotating group:
 C3'(H3'1,H3'2,H3'3), C4'(H4'1,H4'2,H4'3), C5'(H5'1,H5'2,H5'3), C7'(H7'1,H7'2,
 H7'3), C8'(H8'1,H8'2,H8'3), C9'(H9'1,H9'2,H9'3), C12'(H12A,H12B,H12C),
 C13'(H13A,H13B,H13C), C14'(H14A,H14B,H14C), C16'(H16A,H16B,H16C), C17'(H17A,
 H17B,H17C), C18'(H18C,H18D,H18E)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H19)
;
_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 2.016
_oxdiff_exptl_absorpt_empirical_full_min 0.369