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_1556923
_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         'C32 H40 N2 O15, 4(H2 O)'
_chemical_formula_sum            'C32 H48 N2 O19'
_chemical_formula_weight         764.72
_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             2017-09-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7531(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.69983(2)
_cell_length_b                   8.73522(2)
_cell_length_c                   17.77957(3)
_cell_measurement_reflns_used    194137
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.9250
_cell_measurement_theta_min      2.4820
_cell_volume                     1949.419(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -90.00  90.00   1.00    1.00    --    0.00  15.00 240.00  180
  2  \w    -90.00  84.00   1.00    1.00    --    0.00   0.00 180.00  174
  3  \w    -90.00  74.00   1.00    1.00    --    0.00  45.00 150.00  164
  4  \w    -45.00  15.00   1.00    1.00    --    0.00   0.00  60.00   60
  5  \w   -105.00  75.00   1.00    1.00    --  -15.00  60.00  30.00  180
  6  \w   -105.00  75.00   1.00    1.00    --  -15.00  60.00 180.00  180
  7  \w   -105.00  75.00   1.00    1.00    --  -15.00  60.00 210.00  180
  8  \w   -105.00  75.00   1.00    1.00    --  -15.00  60.00 270.00  180
  9  \w    -61.00  26.00   1.00    1.00    --  -15.00  30.00 300.00   87
 10  \w   -105.00 -21.00   1.00    1.00    --  -15.00  60.00 120.00   84
 11  \w     35.00  65.00   1.00    1.00    --  -15.00   0.00 240.00   30
 12  \w    -65.00 -35.00   1.00    1.00    --  -15.00  15.00  60.00   30
 13  \w   -105.00 -75.00   1.00    1.00    --  -15.00  60.00  60.00   30
 14  \w   -105.00 -78.00   1.00    1.00    --  -15.00  60.00 330.00   27
 15  \w   -120.00  60.00   1.00    1.00    --  -30.00  15.00 180.00  180
 16  \w   -120.00  60.00   1.00    1.00    --  -30.00  15.00 270.00  180
 17  \w   -120.00  60.00   1.00    1.00    --  -30.00  60.00 300.00  180
 18  \w   -120.00  60.00   1.00    1.00    --  -30.00  60.00 150.00  180
 19  \w   -120.00  60.00   1.00    1.00    --  -30.00  60.00  90.00  180
 20  \w   -120.00  54.00   1.00    1.00    --  -30.00  60.00   0.00  174
 21  \w   -120.00  45.00   1.00    1.00    --  -30.00  45.00  60.00  165
 22  \w   -120.00  30.00   1.00    1.00    --  -30.00  60.00 210.00  150
 23  \w   -135.00  45.00   1.00    1.00    --  -45.00  15.00 180.00  180
 24  \w   -135.00  45.00   1.00    1.00    --  -45.00  60.00 150.00  180
 25  \w   -135.00  45.00   1.00    1.00    --  -45.00  60.00 210.00  180
 26  \w   -135.00  45.00   1.00    1.00    --  -45.00  60.00 120.00  180
 27  \w   -135.00  45.00   1.00    1.00    --  -45.00  60.00  60.00  180
 28  \w   -135.00  45.00   1.00    1.00    --  -45.00  30.00  30.00  180
 29  \w   -135.00  45.00   1.00    1.00    --  -45.00  60.00 300.00  180
 30  \w   -135.00  45.00   1.00    1.00    --  -45.00  60.00 270.00  180
 31  \w   -135.00  39.00   1.00    1.00    --  -45.00   0.00   0.00  174
 32  \w   -150.00  30.00   1.00    1.00    --  -60.00  15.00 180.00  180
 33  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00 210.00  180
 34  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00 120.00  180
 35  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00 180.00  180
 36  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00   0.00  180
 37  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00  90.00  180
 38  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00 150.00  180
 39  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00  60.00  180
 40  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00 330.00  180
 41  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00 240.00  180
 42  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00 270.00  180
 43  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00  30.00  180
 44  \w   -150.00  30.00   1.00    1.00    --  -60.00  60.00 300.00  180
 45  \w   -123.00 -15.00   1.00    1.00    --  -60.00   0.00 330.00  108
 46  \w    -37.00   8.00   1.00    1.00    --  -60.00  15.00 120.00   45
 47  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00  30.00  180
 48  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00 240.00  180
 49  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00   0.00  180
 50  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00 150.00  180
 51  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00 210.00  180
 52  \w   -165.00  15.00   1.00    1.00    --  -75.00  30.00 300.00  180
 53  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00 150.00  180
 54  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00 180.00  180
 55  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00 330.00  180
 56  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00 300.00  180
 57  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00  30.00  180
 58  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00  60.00  180
 59  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00 270.00  180
 60  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00 330.00  180
 61  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00  60.00  180
 62  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00 120.00  180
 63  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00 210.00  180
 64  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00 180.00  180
 65  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00 300.00  180
 66  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00   0.00  180
 67  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00 270.00  180
 68  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00 120.00  180
 69  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00 240.00  180
 70  \w   -165.00  15.00   1.00    1.00    --  -75.00  60.00  90.00  180
 71  \w   -165.00  15.00   1.00    1.00    --  -75.00  45.00  90.00  180
 72  \w    -25.00   5.00   1.00    1.00    --  -75.00   0.00 240.00   30
 73  \w    -35.00  -5.00   1.00    1.00    --  -75.00  15.00 180.00   30
 74  \w   -165.00-137.00   1.00    1.00    --  -75.00   0.00  30.00   28
 75  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00  60.00  180
 76  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00 210.00  180
 77  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00 120.00  180
 78  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00 150.00  180
 79  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00 300.00  180
 80  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00   0.00  180
 81  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00 180.00  180
 82  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00 240.00  180
 83  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00 180.00  180
 84  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00 330.00  180
 85  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00 270.00  180
 86  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00  30.00  180
 87  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00 210.00  180
 88  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00  90.00  180
 89  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00 120.00  180
 90  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00 330.00  180
 91  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00   0.00  180
 92  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00 240.00  180
 93  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00  90.00  180
 94  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00  60.00  180
 95  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00 300.00  180
 96  \w   -180.00   0.00   1.00    2.00    --  -90.00  60.00 270.00  180
 97  \w   -180.00   0.00   1.00    2.00    --  -90.00  45.00  30.00  180
 98  \w   -180.00   0.00   1.00    2.00    --  -90.00   0.00 120.00  180
 99  \w   -150.00-120.00   1.00    2.00    --  -90.00  15.00   0.00   30
100  \w   -120.00 -90.00   1.00    2.00    --  -90.00  30.00 150.00   30
101  \w   -103.00 -75.00   1.00    2.00    --  -90.00  15.00 210.00   28
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0021378000
_diffrn_orient_matrix_UB_12      0.0037496000
_diffrn_orient_matrix_UB_13      0.0868384000
_diffrn_orient_matrix_UB_21      -0.1197397000
_diffrn_orient_matrix_UB_22      0.0386669000
_diffrn_orient_matrix_UB_23      -0.0119450000
_diffrn_orient_matrix_UB_31      -0.0268743000
_diffrn_orient_matrix_UB_32      -0.1720459000
_diffrn_orient_matrix_UB_33      -0.0007838000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            234667
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.710
_diffrn_reflns_theta_min         2.514
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             812
_exptl_crystal_size_max          1.26
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 3149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         7135
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0350P)^2^+2.1510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                6952
_reflns_number_total             7135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00490_si_002.cif
_cod_data_source_block           urw-49a
_cod_database_code               1556923
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.59
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O8-C6' \\sim O8A-C6'
 with sigma of 0.01
3. Rigid bond restraints
 O8, O8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O8, O8A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O8A, O8
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
O8 \\sim O8A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
O8 \\sim O8A: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.006
Uanis(O8) \\sim Ueq, Uanis(O8A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
5. Others
 Sof(H6'C)=Sof(H6'D)=Sof(O8A)=Sof(H8A)=1-FVAR(1)
 Sof(O8)=Sof(H8)=Sof(H6'A)=Sof(H6'B)=FVAR(1)
6.a Free rotating group:
 O2W(H2WA,H2WB), O1W(H1WA,H1WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB)
6.b Ternary CH refined with riding coordinates:
 C1"(H1"), C1'(H1'), C2"(H2"), C2'(H2'), C3(H3), C3"(H3"), C3'(H3'), C4"(H4"),
 C4'(H4'), C5"(H5"), C5'(H5'), C15(H15), C20(H20), C21(H21)
6.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C6"(H6"A,H6"B), C6'(H6'A,H6'B), C6'(H6'C,H6'D),
 C14(H14A,H14B)
6.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C12(H12A), C17(H17), C19(H19)
6.e Tetrahedral OH refined with riding coordinates:
 O8(H8), O8A(H8A)
6.f X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
6.g Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6), O7(H7), O11(H11), O12(H12), O13(H13), O14(H14)
;
_shelx_res_checksum              22087
_shelx_hkl_checksum              46515
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.816
_oxdiff_exptl_absorpt_empirical_full_min 0.423