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_1548514
_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 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_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                   11.1617(4)
_cell_length_b                   11.3469(3)
_cell_length_c                   15.3512(5)
_cell_measurement_reflns_used    8540
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      62.8090
_cell_measurement_theta_min      4.8260
_cell_volume                     1944.24(11)
_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      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega  -25.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -99.0000  -30.0000 100

  2 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  -30.0000 89

  3 omega   35.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  178.0000 -150.0000 74

  4 omega   19.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -30.0000 58

  5 omega   18.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000    0.0000 51

  6 omega   22.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000   90.0000 90

  7 omega   19.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -180.0000 58

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

  9 omega   35.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000  -30.0000 99

 10 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -120.0000 72

 11 omega   20.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000   90.0000 101

 12 omega   17.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -15.0000 -120.0000 127

 13 omega   19.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 58

 14 omega   18.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -180.0000 51

 15 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -180.0000 72

 16 omega   18.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -90.0000 72

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

 18 omega   19.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  154.5083 110

 19 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000   90.0000 89

 20 omega  -36.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -57.0000 -180.0000 91

 21 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000 -150.0000 100

 22 omega   61.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000    0.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_orient_matrix_UB_11      0.1343120000
_diffrn_orient_matrix_UB_12      -0.0272656000
_diffrn_orient_matrix_UB_13      0.0112598000
_diffrn_orient_matrix_UB_21      0.0113458000
_diffrn_orient_matrix_UB_22      -0.0203185000
_diffrn_orient_matrix_UB_23      -0.0988778000
_diffrn_orient_matrix_UB_31      0.0294878000
_diffrn_orient_matrix_UB_32      0.1314621000
_diffrn_orient_matrix_UB_33      -0.0130774000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15654
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        63.315
_diffrn_reflns_theta_max         63.315
_diffrn_reflns_theta_min         4.846
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       blocks
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_coef       0.0053(6)
_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   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0286
_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^)+(0.0404P)^2^+0.2152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0752
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2968
_reflns_number_total             3104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00606_si_007.cif
_cod_data_source_block           CAOJIAQIANG_CV-B-6
_cod_original_cell_volume        1944.23(11)
_cod_database_code               1548514
_shelx_shelxl_version_number     2016/4
_cell_oxdiff_angle_alpha         89.930(4)
_cell_oxdiff_angle_beta          90.020(4)
_cell_oxdiff_angle_gamma         89.951(4)
_cell_oxdiff_length_a            11.1653(6)
_cell_oxdiff_length_b            11.3453(5)
_cell_oxdiff_length_c            15.3485(7)
_cell_oxdiff_measurement_reflns_used 8540
_cell_oxdiff_volume              1944.23(17)
_reflns_odcompleteness_completeness 97.31
_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:
 C9(H9), C2'(H2'), C6'(H6'), C5A(H5A), C9A(H9A)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7)
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)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'