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_1556920
_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 H32 N2 O9, 2.5(H2 O)'
_chemical_formula_sum            'C26 H37 N2 O11.5'
_chemical_formula_weight         561.57
_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     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                 91.5281(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.46638(8)
_cell_length_b                   22.89580(19)
_cell_length_c                   15.81982(11)
_cell_measurement_reflns_used    14173
_cell_measurement_temperature    120
_cell_measurement_theta_max      68.5620
_cell_measurement_theta_min      4.7120
_cell_volume                     2703.42(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.987
_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    -65.00  89.00   1.00    7.21    --    0.00  29.00 -30.00  154
  2  \w   -112.00 -29.00   1.00   28.84    --  -90.00  55.00  90.00   83
  3  \w   -146.00 -47.00   1.00   28.84    --  -90.00  43.00   0.00   99
  4  \w    -70.00 -27.00   1.00   28.84    --  -90.00  55.00 -60.00   43
  5  \w    -32.00  -1.00   1.00   28.84    --  -90.00  43.00  90.00   31
  6  \w    -26.00  -1.00   1.00   28.84    --  -90.00  55.00  90.00   25
  7  \w   -172.00-131.00   1.00   28.84    --  -90.00  55.00 -60.00   41
  8  \w   -151.00 -55.00   1.00   28.84    --  -90.00  55.00 120.00   96
  9  \w   -154.00  -5.00   1.00   28.84    --  -90.00  29.00 -90.00  149
 10  \w    -85.00 -58.00   1.00   28.84    --  -90.00  55.00  30.00   27
 11  \w   -166.00  -7.00   1.00   28.84    --  -90.00  29.00 -30.00  159
 12  \w   -173.00-135.00   1.00   28.84    --  -90.00  55.00   0.00   38
 13  \w   -172.00  -1.00   1.00   28.84    --  -90.00  55.00  60.00  171
 14  \w   -161.00-135.00   1.00   28.84    --  -90.00  55.00  30.00   26
 15  \w   -163.00-137.00   1.00   28.84    --  -90.00  55.00 -30.00   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      0.1766447000
_diffrn_orient_matrix_UB_12      -0.0205801000
_diffrn_orient_matrix_UB_13      -0.0384473000
_diffrn_orient_matrix_UB_21      0.0170601000
_diffrn_orient_matrix_UB_22      0.0590008000
_diffrn_orient_matrix_UB_23      -0.0459322000
_diffrn_orient_matrix_UB_31      0.1055215000
_diffrn_orient_matrix_UB_32      0.0249536000
_diffrn_orient_matrix_UB_33      0.0767868000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25634
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.384
_diffrn_reflns_theta_min         3.861
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64249
_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    1.380
_exptl_crystal_description       needle
_exptl_crystal_F_000             1196
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.465
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 4237 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       0.0010(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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     736
_refine_ls_number_reflns         9882
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0730P)^2^+1.3740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                9403
_reflns_number_total             9882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00490_si_007.cif
_cod_data_source_block           urw-47a
_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(C26 H32 N2 O9), 5(H2 O)'
_cod_original_formula_sum        'C52 H74 N4 O23'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1123.15
_cod_database_code               1556920
_reflns_odcompleteness_completeness 99.94
_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, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O3W(H3WA,H3WB), O2W(H2WA,H2WB), O4W(H4WA,H4WB), O1W(H1WA,H1WB), O5W(H5WA,H5WB)
2.b Ternary CH refined with riding coordinates:
 C1'(H1'), C2'(H2'), C3(H3), C3'(H3'), C4'(H4'), C5'(H5'), C15(H15), C20(H20),
 C21(H21), C1'A(H1'A), C2'A(H2'A), C3'A(H3'A), C3A(H3A), C4'A(H4'A), C5'A(H5'A),
  C15A(H15A), C20A(H20A), C21A(H21A)
2.c Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C6'(H6'A,H6'B), C14(H14A,H14B),
 N4A(H4AA,H4AB), C5A(H5AB,H5AC), C6'A(H6'C,H6'D), C6A(H6AB,H6AC), C14A(H14C,
 H14D)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9A), C10(H10), C11(H11), C12(H12), C17(H17), C19(H19), N1A(H1A),
 C9A(H9AB), C10A(H10A), C11A(H11A), C12A(H12A), C17A(H17A), C19A(H19A)
2.e X=CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D)
2.f Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6), O7(H7), O9(H9), O5A(H5AA), O6A(H6AA), O7A(H7A), O9A(H9AA)
;
_shelx_res_checksum              76647
_shelx_hkl_checksum              53672
_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 1.780
_oxdiff_exptl_absorpt_empirical_full_min 0.620