Arbutin Derivatives Isolated from Ancient Proteaceae: Potential Phytochemical Markers Present in Bellendena, Cenarrhenes, and Persoonia Genera.
Deans, Bianca J.; Kilah, Nathan L.; Jordan, Gregory J.; Bissember, Alex C.; Smith, Jason A.; Journal of natural products 81 (2018) 1241–1251; doi:10.1021/acs.jnatprod.7b01038

data_1553341
_publ_section_title
;
 Arbutin Derivatives Isolated from Ancient Proteaceae: Potential
 Phytochemical Markers Present in Bellendena, Cenarrhenes, and Persoonia
 Genera.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1241
_journal_page_last               1251
_journal_paper_doi               10.1021/acs.jnatprod.7b01038
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C22 H28 O11'
_chemical_formula_sum            'C22 H28 O11'
_chemical_formula_weight         468.44
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.84(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.958(3)
_cell_length_b                   4.7540(10)
_cell_length_c                   15.974(3)
_cell_measurement_reflns_used    6280
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.729
_cell_measurement_theta_min      1.712
_cell_volume                     1115.6(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20826
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.729
_diffrn_reflns_theta_min         1.712
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1887 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       0.199(13)
_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   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         6280
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0657
_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^)+(0.0598P)^2^+0.2763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.824
_reflns_number_gt                5127
_reflns_number_total             6280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01038_si_006.cif
_cod_data_source_block           Compound8
_cod_database_code               1553341
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.991
_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
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C1(H1), C2(H2), C5(H5A), C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C22(H22A,H22B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C9(H9), C11(H11A), C21(H21), C16(H16)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'