Glucoconjugated Monoterpene Indole Alkaloids from <i>Uncaria rhynchophylla</i>.
Guo, Qiang; Si, Xiali; Shi, Yuntao; Yang, Hongshuai; Liu, Xinyu; Liang, Hong; Tu, Pengfei; Zhang, Qingying; Journal of natural products 82 (2019) 3288–3301; doi:10.1021/acs.jnatprod.9b00490

data_1556924
_publ_section_title
;
 Glucoconjugated Monoterpene Indole Alkaloids from <i>Uncaria
 rhynchophylla</i>.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              3288
_journal_page_last               3301
_journal_paper_doi               10.1021/acs.jnatprod.9b00490
_journal_volume                  82
_journal_year                    2019
_chemical_formula_moiety         'C26 H30 N2 O8, H2 O'
_chemical_formula_sum            'C26 H32 N2 O9'
_chemical_formula_weight         516.53
_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     direct
_audit_creation_date             2018-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.4358(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.01025(11)
_cell_length_b                   9.55452(11)
_cell_length_c                   13.71388(12)
_cell_measurement_reflns_used    11345
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.7620
_cell_measurement_theta_min      4.7890
_cell_volume                     1572.28(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -24.00   1.00   1.00    1.78    --    0.00   9.00 -90.00   25
  2  \w    -90.00 -47.00   1.00    7.14    --  -90.00   9.00 -90.00   43
  3  \w      1.00  28.00   1.00    1.78    --    0.00  55.00-180.00   27
  4  \w     30.00  87.00   1.00    1.78    --    0.00  29.00 -30.00   57
  5  \w    -88.00   7.00   1.00    1.78    --    0.00  29.00  30.00   95
  6  \w    -84.00 -59.00   1.00    1.78    --    0.00  55.00-150.00   25
  7  \w     52.00  88.00   1.00    1.78    --    0.00  14.00 150.00   36
  8  \w    -79.00   6.00   1.00    1.78    --    0.00  29.00 -30.00   85
  9  \w    -26.00  -1.00   1.00    7.14    --  -90.00  55.00 120.00   25
 10  \w   -169.00-116.00   1.00    7.14    --  -90.00  55.00 120.00   53
 11  \w   -140.00-114.00   1.00    7.14    --  -90.00  55.00-120.00   26
 12  \w    -27.00  -1.00   1.00    7.14    --  -90.00  55.00  90.00   26
 13  \w   -179.00  -1.00   1.00    7.14    --  -90.00  29.00 150.00  178
 14  \w    -27.00  -1.00   1.00    7.14    --  -90.00  55.00-180.00   26
 15  \w    -28.00  -1.00   1.00    7.14    --  -90.00  43.00-150.00   27
 16  \w    -26.00  -1.00   1.00    7.14    --  -90.00  43.00 120.00   25
 17  \w    -28.00  -1.00   1.00    7.14    --  -90.00  43.00  90.00   27
 18  \w    -27.00  -1.00   1.00    7.14    --  -90.00  43.00-180.00   26
 19  \w    -26.00  -1.00   1.00    7.14    --  -90.00  55.00-150.00   25
 20  \w   -178.00 -74.00   1.00    7.14    --  -90.00  55.00  60.00  104
 21  \w    -26.00  -1.00   1.00    7.14    --  -90.00  55.00 -90.00   25
 22  \w    -27.00  -1.00   1.00    7.14    --  -90.00  43.00-120.00   26
 23  \w    -27.00  -1.00   1.00    7.14    --  -90.00  43.00 150.00   26
 24  \w    -26.00  -1.00   1.00    7.14    --  -90.00  29.00 120.00   25
 25  \w   -136.00-109.00   1.00    7.14    --  -90.00  55.00-150.00   27
 26  \w    -26.00  -1.00   1.00    7.14    --  -90.00  55.00-120.00   25
 27  \w    -26.00  -1.00   1.00    7.14    --  -90.00  55.00 150.00   25
 28  \w    -45.00  -2.00   1.00    7.14    --  -90.00  43.00 -90.00   43
 29  \w   -142.00  -3.00   1.00    7.14    --  -90.00  29.00-180.00  139
 30  \w   -149.00  -5.00   1.00    7.14    --  -90.00  29.00-150.00  144
 31  \w   -164.00-137.00   1.00    7.14    --  -90.00  29.00-120.00   27
 32  \w   -115.00  -1.00   1.00    7.14    --  -90.00  29.00-120.00  114
 33  \w    -27.00  -2.00   1.00    7.14    --  -90.00  29.00  90.00   25
 34  \w   -139.00-112.00   1.00    7.14    --  -90.00  55.00 150.00   27
 35  \w    -24.00   1.00   1.00    1.78    --    0.00   9.00 -88.00   25
 36  \w   -159.00-133.00   1.00    7.14    --  -90.00  55.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1189175000
_diffrn_orient_matrix_UB_12      -0.0250575000
_diffrn_orient_matrix_UB_13      -0.0341369000
_diffrn_orient_matrix_UB_21      0.0445299000
_diffrn_orient_matrix_UB_22      -0.0007061000
_diffrn_orient_matrix_UB_23      0.1070106000
_diffrn_orient_matrix_UB_31      -0.0189142000
_diffrn_orient_matrix_UB_32      -0.1592945000
_diffrn_orient_matrix_UB_33      0.0048930000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20615
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.237
_diffrn_reflns_theta_min         3.684
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       needle
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_coef       0.0006(3)
_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   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5485
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0650P)^2^+0.1640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.862
_reflns_number_gt                5259
_reflns_number_total             5485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00490_si_005.cif
_cod_data_source_block           urw_12a
_cod_database_code               1556924
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C1'(H1'), C2'(H2'), C3(H3), C3'(H3'), C4'(H4'), C5'(H5'), C15(H15), C20(H20)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C6'(H6'A,H6'B), C14(H14A,H14B), C21(H21A,H21B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C11(H11), C12(H12), C17(H17), C19(H19)
2.e X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O6(H6), O8(H8)
;
_shelx_res_checksum              92023
_shelx_hkl_checksum              73628
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.633