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_1553340
_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 rmad
_chemical_formula_moiety         'C12 H16 O7, H2 O'
_chemical_formula_sum            'C12 H18 O8'
_chemical_formula_weight         290.26
_chemical_name_systematic        'Arbutin hydrate'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.7584(2)
_cell_length_b                   14.2353(4)
_cell_length_c                   27.7506(8)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.05
_cell_measurement_theta_min      3.10
_cell_volume                     2669.83(13)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0437
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20575
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        60.100
_diffrn_reflns_theta_max         60.100
_diffrn_reflns_theta_min         3.185
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.056
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1180 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.8619.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1454 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(9)
_refine_ls_extinction_coef       0.0023(2)
_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   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0211P)^2^+1.6317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0711
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3647
_reflns_number_total             3908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01038_si_005.cif
_cod_data_source_block           Compound4
_cod_database_code               1553340
_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 O(H) groups, All O(H,H) groups
2. Restrained distances
 H30D-O302
 0.85 with sigma of 0.0001
 O103-H30D_$1
 2.04 with sigma of 0.02
 H30D-H30C
 1.35 with sigma of 0.02
3.a Free rotating group:
 O301(H30A,H30B), O302(H30C)
3.b Ternary CH refined with riding coordinates:
 C103(H10A), C204(H20A), C101(H101), C105(H10B), C102(H102), C104(H10C),
 C205(H20B), C201(H201), C203(H20E), C202(H202)
3.c Secondary CH2 refined with riding coordinates:
 C106(H10D,H10E), C206(H20C,H20D)
3.d Aromatic/amide H refined with riding coordinates:
 C212(H212), C211(H211), C108(H108), C208(H208), C109(H109), C112(H112),
 C209(H209), C111(H111)
3.e Idealised tetrahedral OH refined as rotating group:
 O104(H104), O204(H204), O106(H106), O103(H103), O105(H105), O205(H205),
 O206(H206), O203(H203), O207(H207), O107(H107)
;
_olex2_submission_special_instructions 'No special instructions were received'