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_1556926
_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 O13'
_chemical_formula_sum            'C32 H40 N2 O13'
_chemical_formula_weight         660.66
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.6535(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.4386(3)
_cell_length_b                   6.02603(8)
_cell_length_c                   18.7078(3)
_cell_measurement_reflns_used    30220
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.8020
_cell_measurement_theta_min      2.3650
_cell_volume                     1959.44(5)
_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 0.996
_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    -90.00  90.00   1.00    3.00    --    0.00  15.00   0.00  180
  2  \w    -90.00  90.00   1.00    3.00    --    0.00  15.00 300.00  180
  3  \w     20.00  50.00   1.00    3.00    --    0.00  30.00 150.00   30
  4  \w      0.00  30.00   1.00    3.00    --    0.00  15.00 330.00   30
  5  \w    -20.00   8.00   1.00    3.00    --    0.00  15.00  30.00   28
  6  \w    -90.00 -69.00   1.00    3.00    --    0.00  30.00  30.00   21
  7  \w   -110.00  70.00   1.00    5.00    --  -20.00  60.00  30.00  180
  8  \w   -110.00  68.00   1.00    5.00    --  -20.00  60.00  60.00  178
  9  \w   -110.00  62.00   1.00    5.00    --  -20.00  45.00 330.00  172
 10  \w    -48.00  48.00   1.00    5.00    --  -20.00   0.00 300.00   96
 11  \w   -135.00  45.00   1.00    8.00    --  -45.00   0.00 150.00  180
 12  \w   -135.00  45.00   1.00    8.00    --  -45.00  60.00 180.00  180
 13  \w   -135.00  45.00   1.00    8.00    --  -45.00  45.00 120.00  180
 14  \w   -135.00  45.00   1.00    8.00    --  -45.00  60.00  90.00  180
 15  \w   -134.00  40.00   1.00    8.00    --  -45.00  60.00  30.00  174
 16  \w   -160.00  20.00   1.00   15.00    --  -70.00   0.00   0.00  180
 17  \w   -160.00  20.00   1.00   15.00    --  -70.00  45.00 180.00  180
 18  \w   -160.00  20.00   1.00   15.00    --  -70.00  45.00 150.00  180
 19  \w   -160.00  20.00   1.00   15.00    --  -70.00  45.00 210.00  180
 20  \w   -160.00  20.00   1.00   15.00    --  -70.00  60.00 210.00  180
 21  \w   -160.00  20.00   1.00   15.00    --  -70.00  45.00 120.00  180
 22  \w   -160.00  20.00   1.00   15.00    --  -70.00  60.00 180.00  180
 23  \w   -160.00  20.00   1.00   15.00    --  -70.00  45.00  90.00  180
 24  \w   -160.00  20.00   1.00   15.00    --  -70.00  60.00 150.00  180
 25  \w   -160.00  20.00   1.00   15.00    --  -70.00  60.00 120.00  180
 26  \w   -160.00  20.00   1.00   15.00    --  -70.00  60.00  90.00  180
 27  \w   -180.00   0.00   1.00   25.00    --  -90.00  45.00 210.00  180
 28  \w   -180.00   0.00   1.00   25.00    --  -90.00  45.00 150.00  180
 29  \w   -180.00   0.00   1.00   25.00    --  -90.00  45.00 180.00  180
 30  \w   -180.00   0.00   1.00   25.00    --  -90.00  60.00 210.00  180
 31  \w   -180.00   0.00   1.00   25.00    --  -90.00  60.00 240.00  180
 32  \w   -180.00   0.00   1.00   25.00    --  -90.00  60.00 180.00  180
 33  \w   -180.00   0.00   1.00   25.00    --  -90.00  45.00  90.00  180
 34  \w   -180.00  -3.00   1.00   25.00    --  -90.00  45.00 120.00  177
 35  \w   -180.00   0.00   1.00   25.00    --  -90.00  60.00 150.00  180
 36  \w   -180.00   0.00   1.00   25.00    --  -90.00  60.00 120.00  180
 37  \w   -180.00   0.00   1.00   25.00    --  -90.00  60.00  90.00  180
 38  \w   -180.00-140.00   1.00   25.00    --  -90.00  60.00  60.00   40
 39  \w   -100.00 -70.00   1.00   25.00    --  -90.00  45.00 240.00   30
 40  \w   -110.00 -80.00   1.00   25.00    --  -90.00   0.00 300.00   30
;
_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      0.0077470000
_diffrn_orient_matrix_UB_12      0.0427094000
_diffrn_orient_matrix_UB_13      -0.0802761000
_diffrn_orient_matrix_UB_21      -0.0880347000
_diffrn_orient_matrix_UB_22      -0.0154955000
_diffrn_orient_matrix_UB_23      -0.0147980000
_diffrn_orient_matrix_UB_31      -0.0067131000
_diffrn_orient_matrix_UB_32      0.2515560000
_diffrn_orient_matrix_UB_33      0.0128506000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1674
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            87011
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.831
_diffrn_reflns_theta_min         2.370
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55220
_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    1.120
_exptl_crystal_description       needle
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 1186 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         7101
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0961
_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^)+(0.1860P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2576
_refine_ls_wR_factor_ref         0.2942
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4549
_reflns_number_total             7101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00490_si_003.cif
_cod_data_source_block           urw-24a
_cod_original_cell_volume        1959.44(6)
_cod_database_code               1556926
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.71
_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
2. Restrained distances
 C6A'-C5' \\sim C6B'-C5'
 with sigma of 0.01
 O8A-C6A' \\sim O8B-C6B'
 with sigma of 0.02
3. Rigid bond restraints
 C6A', C6B'
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O8A, O8B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C6A' \\sim C6B': within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.06
C6A' \\sim C6B': within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.05
O8A \\sim O8B: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.06
Uanis(C6B') \\sim Ueq, Uanis(C6A') \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.08
Uanis(C6B') \\sim Ueq, Uanis(C6A') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.06
Uanis(O8B) \\sim Ueq, Uanis(O8A) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.09
5. Others
 Sof(H5'A)=Sof(O8B)=Sof(H8B)=Sof(C6B')=Sof(H6BA)=Sof(H6BB)=1-FVAR(1)
 Sof(H5')=Sof(O8A)=Sof(H8A)=Sof(C6A')=Sof(H6AA)=Sof(H6AB)=FVAR(1)
6.a 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'), C5'(H5'A), C15(H15), C20(H20), C21(H21)
6.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C6"(H6"A,H6"B), C14(H14A,H14B), C6A'(H6AA,H6AB),
 C6B'(H6BA,H6BB)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9A), C10(H10A), C11(H11A), C12(H12), C17(H17), C19(H19)
6.d Tetrahedral OH refined with riding coordinates:
 O8A(H8A), O8B(H8B)
6.e X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
6.f Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6), O9(H9), O10(H10), O11(H11), O13(H13)
;
_shelx_res_checksum              7064
_shelx_hkl_checksum              33736
_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 2.107
_oxdiff_exptl_absorpt_empirical_full_min 0.599