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_1556925
_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_absolute_configuration unk
_chemical_formula_moiety         'C27 H34 N2 O10, 0.5(H2 O)'
_chemical_formula_sum            'C27 H35 N2 O10.5'
_chemical_formula_weight         555.57
_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     dual
_audit_creation_date             2019-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.341(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6115(15)
_cell_length_b                   8.4248(4)
_cell_length_c                   21.2254(16)
_cell_measurement_reflns_used    3323
_cell_measurement_temperature    100
_cell_measurement_theta_max      63.0350
_cell_measurement_theta_min      4.7960
_cell_volume                     3140.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_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_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_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    -52.00  24.00   0.50   12.00    --  -47.45  24.00  33.00  152
  2  \w     36.00 101.00   0.50   12.00    --   47.45  24.00  33.00  130
  3  \w     96.00 146.00   0.50   80.00    --  103.25  24.00  33.00  100
  4  \w     82.00 109.00   0.50   80.00    --  103.25 -24.00-131.00   54
  5  \w     55.00 106.00   0.50   80.00    --  103.25 -94.00 -60.00  102
  6  \w     38.00 110.00   0.50   80.00    --  103.25 -61.00 -30.00  144
  7  \w     45.00  95.00   0.50   80.00    --  103.25 -94.00 -90.00  100
  8  \w     31.00 105.00   0.50   80.00    --  103.25 -94.00-180.00  148
  9  \w     -7.00  18.00   0.50   12.00    --   47.45 -24.00-131.00   50
 10  \w   -115.00 -34.00   0.50   12.00    --  -47.45 -24.00-131.00  162
 11  \w   -113.00 -28.00   0.50   80.00    -- -101.00  24.00  33.00  170
 12  \w   -150.00 -95.00   0.50   80.00    -- -101.00 -24.00-131.00  110
 13  \w     28.00  93.00   0.50   12.00    --   47.45-125.00 150.00  130
 14  \w     61.00 106.00   0.50   80.00    --  103.25 -94.00 120.00   90
 15  \w     75.00 107.00   0.50   80.00    --  103.25 -30.00 120.00   64
 16  \w     34.00  60.00   0.50   80.00    --  103.25-125.00 120.00   52
 17  \w     33.00  58.00   0.50   80.00    --  103.25 -94.00 120.00   50
 18  \w     30.00  56.00   0.50   80.00    --  103.25 -30.00 120.00   52
 19  \w    110.00 135.00   0.50   80.00    --  103.25  24.00  32.00   50
 20  \w     64.00 111.00   0.50   80.00    --  103.25 -45.00  60.00   94
 21  \w   -102.00 -77.00   0.50   12.00    --  -47.70 -24.00-131.00   50
 22  \w     71.00  97.00   0.50   80.00    --  103.25 -94.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0161976000
_diffrn_orient_matrix_UB_12      -0.0381839000
_diffrn_orient_matrix_UB_13      0.0649826000
_diffrn_orient_matrix_UB_21      0.0826787000
_diffrn_orient_matrix_UB_22      0.0441149000
_diffrn_orient_matrix_UB_23      0.0409356000
_diffrn_orient_matrix_UB_31      -0.0246341000
_diffrn_orient_matrix_UB_32      0.1732828000
_diffrn_orient_matrix_UB_33      0.0038084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            23414
_diffrn_reflns_point_group_measured_fraction_full 0.742
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.814
_diffrn_reflns_theta_min         3.858
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
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    1.175
_exptl_crystal_description       needle
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         9178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0858
_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^)+(0.1720P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2291
_refine_ls_wR_factor_ref         0.2570
_reflns_Friedel_coverage         0.364
_reflns_Friedel_fraction_full    0.446
_reflns_Friedel_fraction_max     0.403
_reflns_number_gt                5570
_reflns_number_total             9178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00490_si_004.cif
_cod_data_source_block           urw_11g
_cod_depositor_comments
;

2022-05-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C27 H34 N2 O10), H2 O'
_cod_original_formula_sum        'C54 H70 N4 O21'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1111.14
_cod_database_code               1556925
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.949
_diffrn_oxdiff_digest_frames
;
01264835a368c74ebff764a702d8fb72c602106d855
;
_diffrn_oxdiff_digest_hkl
;
01635b98875a72dd84dc2dd04a1e9eb88c184e
;
_reflns_odcompleteness_completeness 99.83
_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:
 C1A'(H1A'), C2A'(H2A'), C3A(H3A), C3A'(H3A'), C4A'(H4A'), C5A'(H5A'),
 C15A(H15A), C19A(H19A), C20A(H20A), C21A(H21A), C1B'(H1B'), C2B'(H2B'),
 C3B(H3B), C3B'(H3B'), C4B'(H4B'), C5B'(H5B'), C15B(H15B), C19B(H19B),
 C20B(H20B), C21B(H21B)
2.c Secondary CH2 refined with riding coordinates:
 C5A(H5Aa,H5Ab), C6A(H6Aa,H6Ab), C6A'(H6Ac,H6Ad), C14A(H14a,H14b), C18A(H18a,
 H18b), C5B(H5Ba,H5Bb), C6B(H6Ba,H6Bb), C6B'(H6Bc,H6Bd), C14B(H14c,H14d),
 C18B(H18c,H18d)
2.d Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C9A(H9Aa), C10A(H10A), C11A(H11A), C12A(H12A), C17A(H17A), N1B(H1B),
  C9B(H9Ba), C10B(H10B), C11B(H11B), C12B(H12B), C17B(H17B)
2.e Tetrahedral OH refined with riding coordinates:
 O9B(H9B)
2.f Idealised Me refined with riding coordinates:
 C23A(H23a,H23b,H23c)
2.g Idealised Me refined as rotating group:
 C23B(H23d,H23e,H23f)
2.h Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O6A(H6A), O7A(H7A), O8A(H8A), O9A(H9A), O2B(H2B), O6B(H6B),
 O7B(H7B), O8B(H8B)
;
_shelx_res_checksum              91166
_shelx_hkl_checksum              83480
_shelx_fab_checksum              56782
_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 3.045
_oxdiff_exptl_absorpt_empirical_full_min 0.460