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_1553343
_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         'C17 H22 O9, H2 O'
_chemical_formula_sum            'C17 H24 O10'
_chemical_formula_weight         388.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.8796(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2391(4)
_cell_length_b                   6.4146(2)
_cell_length_c                   19.8531(6)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.43
_cell_measurement_theta_min      4.48
_cell_volume                     1803.81(9)
_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  'enCIFer (Allen, 1997)'
_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_detector_area_resol_mean 10.4
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator
'Bruker multilayer X-ray optics (Goebel mirror)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12624
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.424
_diffrn_reflns_theta_min         4.478
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0688 before and 0.0247 after correction.
The Ratio of minimum to maximum transmission is 0.8308.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3398
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0853P)^2^+0.8945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1158
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                3363
_reflns_number_total             3398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01038_si_007.cif
_cod_data_source_block           Compound9
_cod_database_code               1553343
_shelx_shelxl_version_number     2014/7
_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:
 C3(H3A), C4(H4A), C5(H5A), C2(H2), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C9(H9A), C8(H8), C16(H16)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'