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_1556922
_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         'C29 H32 N2 O11, H2 O'
_chemical_formula_sum            'C29 H34 N2 O12'
_chemical_formula_weight         602.58
_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     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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.15738(19)
_cell_length_b                   10.7672(2)
_cell_length_c                   33.9634(7)
_cell_measurement_reflns_used    10001
_cell_measurement_temperature    120
_cell_measurement_theta_max      68.7980
_cell_measurement_theta_min      4.2910
_cell_volume                     2983.08(11)
_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      120
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_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   -127.00-100.00   1.00   80.89    --  -90.00  16.00 -57.00   27
  2  \w   -178.00-140.00   1.00   80.89    --  -90.00  16.00 -57.00   38
  3  \w     48.00  74.00   1.00   20.23    --    0.00  55.00-180.00   26
  4  \w    -48.00  -5.00   1.00   20.23    --    0.00  55.00-180.00   43
  5  \w    -88.00   1.00   1.00   20.23    --    0.00  16.00 -57.00   89
  6  \w     46.00  71.00   1.00   20.23    --    0.00  16.00 -57.00   25
  7  \w    -31.00  -4.00   1.00   80.89    --  -90.00  55.00 120.00   27
  8  \w   -151.00  -2.00   1.00   80.89    --  -90.00  55.00  60.00  149
  9  \w   -166.00-124.00   1.00   80.89    --  -90.00  55.00 120.00   42
 10  \w   -160.00 -62.00   1.00   80.89    --  -90.00  55.00  30.00   98
 11  \w    -43.00  -5.00   1.00   80.89    --  -90.00  55.00  30.00   38
 12  \w    -44.00 -17.00   1.00   80.89    --  -90.00   0.00-180.00   27
 13  \w    -96.00  -4.00   1.00   80.89    --  -90.00  43.00 -90.00   92
 14  \w    -79.00 -49.00   1.00   20.23    --    0.00  16.00 -55.00   30
 15  \w     -1.00  35.00   1.00   20.23    --    0.00  16.00 -55.00   36
 16  \w    -89.00 -61.00   1.00   20.23    --    0.00  29.00  30.00   28
 17  \w     40.00  78.00   1.00   20.23    --    0.00  55.00-150.00   38
 18  \w     49.00  87.00   1.00   20.23    --    0.00  29.00  30.00   38
 19  \w    -14.00  11.00   1.00   20.23    --    0.00  29.00  30.00   25
 20  \w     -3.00  22.00   1.00   20.23    --    0.00  55.00 -60.00   25
 21  \w    -42.00 -17.00   1.00   20.23    --    0.00  55.00  90.00   25
 22  \w    -26.00  -1.00   1.00   80.89    --  -90.00  55.00-180.00   25
 23  \w   -139.00 -49.00   1.00   80.89    --  -90.00  55.00-180.00   90
 24  \w    -28.00  -1.00   1.00   80.89    --  -90.00  29.00-180.00   27
;
_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      0.0682497000
_diffrn_orient_matrix_UB_12      -0.0314799000
_diffrn_orient_matrix_UB_13      0.0410735000
_diffrn_orient_matrix_UB_21      -0.1758010000
_diffrn_orient_matrix_UB_22      -0.0210309000
_diffrn_orient_matrix_UB_23      0.0152035000
_diffrn_orient_matrix_UB_31      0.0112776000
_diffrn_orient_matrix_UB_32      -0.1379817000
_diffrn_orient_matrix_UB_33      -0.0117315000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            20256
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.455
_diffrn_reflns_theta_min         4.308
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64356
_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            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0390P)^2^+1.3630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5032
_reflns_number_total             5485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00490_si_006.cif
_cod_data_source_block           urw_43a
_cod_original_cell_volume        2983.07(11)
_cod_database_code               1556922
_reflns_odcompleteness_completeness 99.90
_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 C(H,H,H) groups, 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'), C4'(H4'), C5'(H5'), C15(H15), C20(H20), C21(H21)
2.c Secondary CH2 refined with riding coordinates:
 C6'(H6'A,H6'B), C14(H14A,H14B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C9(H9A), C10(H10A), C11(H11), C12(H12), C17(H17), C19(H19)
2.e X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.f Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
2.g Idealised tetrahedral OH refined as rotating group:
 O7(H7), O8(H8), O9(H9), O10(H10)
;
_shelx_res_checksum              82838
_shelx_hkl_checksum              75870
_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 1.631
_oxdiff_exptl_absorpt_empirical_full_min 0.530