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_1553342
_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         'C17 H22 O9'
_chemical_formula_sum            'C17 H22 O9'
_chemical_formula_weight         370.34
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                86.40(3)
_cell_angle_beta                 88.07(3)
_cell_angle_gamma                80.31(3)
_cell_formula_units_Z            2
_cell_length_a                   4.9000(10)
_cell_length_b                   12.500(3)
_cell_length_c                   14.550(3)
_cell_measurement_reflns_used    32163
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.627
_cell_measurement_theta_min      1.655
_cell_volume                     876.5(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_type            'Bruker AXS PHOTON-100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.840
_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  0.0259
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32163
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.789
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.627
_diffrn_reflns_theta_min         1.655
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       needle
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 3847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(18)
_refine_ls_extinction_coef       0.32(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   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         9310
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0921P)^2^+0.2737P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.738
_reflns_number_gt                8760
_reflns_number_total             9310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b01038_si_004.cif
_cod_data_source_block           Compound2
_cod_database_code               1553342
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
The refinement revealed that the side chain of one of the two molecules in 
the asymmetric unit was disordered. The disorder was visible in the 
Fourier difference map, and efforts were made to refine this disorder over 
two sites. Numerous restraints were used to try to keep the modeled atoms at
chemically reasonable distances and angles. A Mogul analysis was used to determine 
the distances and angles appropriate for restaints. Residual electron density 
indicated possible additional disorder, but no attempt was made to model it.

The majority of hydrogen atoms were visible in the difference map. Hydrogen 
atoms on carbon were included at calculated positions and ride on the atoms 
to which they are attached. Hydrogen atoms on oxygen were included at their 
observed positions, and their positions were refined. Hydrogen atoms not 
visible in the difference map were included using the Olex2 hadd process.

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
2. Restrained distances
 C213-C214
 1.49 with sigma of 0.02
 C213-C314
 1.49 with sigma of 0.02
 C215-C214
 1.32 with sigma of 0.02
 C315-C314
 1.32 with sigma of 0.02
 C214-C216
 1.51 with sigma of 0.02
 C314-C316
 1.51 with sigma of 0.02
 C316-C317
 1.51 with sigma of 0.02
 C216-C217
 1.51 with sigma of 0.02
 O209-C217
 1.51 with sigma of 0.02
 C217-O209
 1.42 with sigma of 0.02
 C317-O309
 1.42 with sigma of 0.02
3. Restrained angles
 C315-C314-C213
 fixed at 120 with sigma of 0.02
 C315-C314-C316
 fixed at 120 with sigma of 0.02
 C213-C214-C215
 fixed at 120 with sigma of 0.02
 C215-C214-C216
 fixed at 120 with sigma of 0.02
 C213-C314-C315
 fixed at 120 with sigma of 0.02
 C316-C314-C315
 fixed at 120 with sigma of 0.02
 O208-C213-C214
 fixed at 123.6 with sigma of 0.02
 O208-C213-C314
 fixed at 123.6 with sigma of 0.02
 O309-C317-C316
 fixed at 111 with sigma of 0.02
 O209-C217-C216
 fixed at 111 with sigma of 0.02
 C213-C214-C216
 fixed at 116 with sigma of 0.02
 C213-C314-C316
 fixed at 116 with sigma of 0.02
4. Rigid bond restraints
 C215, C214, C216, C217, O209
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C315, C314, C316, C317, O309
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Others
 Sof(C315)=Sof(H31A)=Sof(H31B)=Sof(C316)=Sof(H31C)=Sof(H31D)=Sof(C317)=
 Sof(H31E)=Sof(H31F)=Sof(O309)=Sof(H309)=Sof(C314)=1-FVAR(1)
 Sof(C214)=Sof(C215)=Sof(H21A)=Sof(H21B)=Sof(C217)=Sof(H21C)=Sof(H21D)=
 Sof(O209)=Sof(H20F)=Sof(C216)=Sof(H21E)=Sof(H21F)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C101(H101), C102(H102), C204(H20A), C105(H10C), C202(H202), C103(H10D),
 C203(H20B), C201(H201), C104(H10E), C205(H20C)
6.b Secondary CH2 refined with riding coordinates:
 C106(H10A,H10B), C117(H11A,H11B), C116(H11C,H11D), C206(H20D,H20E), C217(H21C,
 H21D), C316(H31C,H31D), C317(H31E,H31F), C216(H21E,H21F)
6.c Aromatic/amide H refined with riding coordinates:
 C109(H10F), C209(H209), C112(H112), C111(H111), C208(H208), C108(H108),
 C211(H211), C212(H212)
6.d Tetrahedral OH refined with riding coordinates:
 O309(H309)
6.e X=CH2 refined with riding coordinates:
 C115(H11E,H11F), C215(H21A,H21B), C315(H31A,H31B)
6.f Idealised tetrahedral OH refined as rotating group:
 O107(H107), O209(H20F)
;
_olex2_submission_special_instructions 'No special instructions were received'