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_1548511
_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 O4'
_chemical_formula_sum            'C22 H30 O4'
_chemical_formula_weight         358.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-19
_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                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.87979(13)
_cell_length_b                   12.7869(2)
_cell_length_c                   17.5805(3)
_cell_measurement_reflns_used    8050
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      62.8090
_cell_measurement_theta_min      3.4570
_cell_volume                     1996.18(5)
_computing_cell_refinement       'CrysAlis PRO '
_computing_data_collection       'CrysAlis PRO '
_computing_data_reduction        'CrysAlis PRO '
_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      173.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000  -30.0000 52

  2 omega   32.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184 -178.0000  -30.0000 78

  3 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000   30.0000 98

  4 omega   18.00   69.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 51

  5 omega   19.00   83.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -95.0000   90.0000 64

  6 omega   18.00   69.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 51

  7 omega   19.00   83.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -95.0000  -90.0000 64

  8 omega   18.00   69.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -120.0000 51

  9 omega   64.00  159.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000   71.0000 -161.1961 95

 10 omega   79.00  163.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  120.0000 84

 11 omega   18.00   90.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -30.0000 72

 12 omega   69.00  159.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -180.0000 90

 13 omega   18.00   90.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000    0.0000 72

 14 omega   19.00   83.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -95.0000   60.0000 64

 15 omega   69.00  159.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -120.0000 90

 16 omega   18.00   69.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   60.0000 51

 17 omega   19.00   77.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -150.0000 58

 18 omega   19.00   92.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -118.0000  -71.0000 73

 19 omega   20.00  121.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000  -60.0000 101

 20 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000  120.0000 100

 21 omega   35.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  178.0000  120.0000 74

 22 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000   60.0000 100

 23 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000 -120.0000 100

 24 omega   69.00   98.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000    0.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      0.0230073000
_diffrn_orient_matrix_UB_12      -0.0564671000
_diffrn_orient_matrix_UB_13      -0.0765061000
_diffrn_orient_matrix_UB_21      0.0860887000
_diffrn_orient_matrix_UB_22      -0.0882442000
_diffrn_orient_matrix_UB_23      0.0410531000
_diffrn_orient_matrix_UB_31      -0.1487536000
_diffrn_orient_matrix_UB_32      -0.0595984000
_diffrn_orient_matrix_UB_33      0.0119058000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16098
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        62.789
_diffrn_reflns_theta_max         62.789
_diffrn_reflns_theta_min         5.031
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       blocks
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_extinction_coef       0.0036(5)
_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   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0469P)^2^+0.4375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3058
_reflns_number_total             3194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00606_si_006.cif
_cod_data_source_block           CAOJIAQING_CV-B-9
_cod_original_cell_volume        1996.18(6)
_cod_database_code               1548511
_shelx_shelxl_version_number     2016/4
_cell_oxdiff_angle_alpha         89.934(4)
_cell_oxdiff_angle_beta          90.012(4)
_cell_oxdiff_angle_gamma         89.916(4)
_cell_oxdiff_length_a            8.8844(4)
_cell_oxdiff_length_b            12.7816(6)
_cell_oxdiff_length_c            17.5788(8)
_cell_oxdiff_measurement_reflns_used 8050
_cell_oxdiff_volume              1996.18(16)
_reflns_odcompleteness_completeness 97.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_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:
 C8(H8), C3'(H3'), C7'(H7'), C9A(H9A1)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C2'(H2'1,H2'2)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C4'(H4'1,H4'2,H4'3), C5'(H5'1,H5'2,H5'3), C6'(H6'1,H6'2,H6'3), C8'(H8'1,H8'2,
 H8'3), C9'(H9'1,H9'2,H9'3), C10'(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'