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_1556921
_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 ad
_chemical_formula_moiety         'C26 H32 N2 O10, 1.5(H2 O)'
_chemical_formula_sum            'C26 H35 N2 O11.5'
_chemical_formula_weight         559.56
_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     dual
_audit_creation_date             2019-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6664(2)
_cell_length_b                   8.4625(3)
_cell_length_c                   52.2037(14)
_cell_measurement_reflns_used    4108
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.4520
_cell_measurement_theta_min      7.8490
_cell_volume                     2503.27(14)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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   -119.00 -71.00   0.15    0.12    --  -47.45 -48.00   8.00  320
  2  \w   -161.00 -87.95   0.15    0.47    -- -101.00 -48.00   8.00  487
  3  \w   -173.00-131.90   0.15    0.47    -- -101.00 -97.00 148.00  274
  4  \w    146.00 173.00   0.15    0.47    --  103.25  83.00   4.00  180
  5  \w    -95.00 -17.00   0.15    0.12    --  -47.45 125.00 150.00  520
  6  \w     41.00 106.10   0.15    0.12    --   47.45  37.00   0.00  434
  7  \w   -134.00 -80.00   0.15    0.47    -- -101.00 -83.00-117.00  360
  8  \w    142.00 173.95   0.15    0.47    --  103.25  61.00  90.00  213
  9  \w    109.00 173.05   0.15    0.47    --  103.25  77.00  60.00  427
 10  \w    104.00 168.05   0.15    0.47    --  103.25  45.00 120.00  427
 11  \w     71.00  96.20   0.15    0.47    --  103.25 -94.00   0.00  168
 12  \w     31.00  57.10   0.15    0.47    --  103.25 -94.00   0.00  174
 13  \w     88.00 129.10   0.15    0.47    --  103.25  61.00  90.00  274
;
_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      -0.0191692000
_diffrn_orient_matrix_UB_12      -0.0872130000
_diffrn_orient_matrix_UB_13      -0.0258140000
_diffrn_orient_matrix_UB_21      -0.1600370000
_diffrn_orient_matrix_UB_22      0.1326181000
_diffrn_orient_matrix_UB_23      -0.0103584000
_diffrn_orient_matrix_UB_31      0.2189422000
_diffrn_orient_matrix_UB_32      0.0891625000
_diffrn_orient_matrix_UB_33      -0.0098579000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            10645
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         3.386
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39572
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       needle
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 1473 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.23(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0770
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0820P)^2^+6.6081P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1945
_refine_ls_wR_factor_ref         0.1993
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4125
_reflns_number_total             4432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00490_si_008.cif
_cod_data_source_block           f77_c_6_1_2_20190605d
_cod_original_formula_sum        'C26 H35 N2 O11.50'
_cod_database_code               1556921
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.916
_diffrn_oxdiff_digest_frames
;
01e6c437ca22455a30b913ff098f9b9d46042581507
;
_diffrn_oxdiff_digest_hkl
;
018efa19c3f03782a9546ea5ae79614ab276d6
;
_reflns_odcompleteness_completeness 99.70
_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 O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H1B(0.5) H1A(0.5) C18B(0.5) H18B(0.5) O19B(0.5) H19B(0.5)
 O21A(0.5) H21A(0.5) O21B(0.5) H21B(0.5) O19A(0.5) H19A(0.5) O2W(0.5) H2WA(0.5)
 H2WB(0.5) C20B(0.5) H20A(0.5) H20B(0.5) C18A(0.5) H18A(0.5) C20A(0.5)
 H20C(0.5) H20D(0.5)
 Fixed X: H2WA(0.54162) H2WB(0.390181)
 Fixed Y: H2WA(0.74986) H2WB(0.62279)
 Fixed Z: H2WA(0.623061) H2WB(0.623231)
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Ternary CH refined with riding coordinates:
 C15(H15), C1(H1B), C1(H1A), C31(H31), C17(H17), C27(H27), C30(H30), C29(H29),
 C2(H2), C32(H32), C18B(H18B), C18A(H18A)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B), C16(H16A,H16B), C36(H36A,H36B), C20B(H20A,H20B),
 C20A(H20C,H20D)
3.d Aromatic/amide H refined with riding coordinates:
 N13(H13), C4(H4), C25(H25), C24(H24), C22(H22), C23(H23)
3.e Tetrahedral OH refined with riding coordinates:
 O37(H37), O35(H35), O34(H34), O33(H33)
3.f Idealised tetrahedral OH refined with riding coordinates:
 O19B(H19B)
3.g Idealised tetrahedral OH refined as rotating group:
 O21A(H21A), O21B(H21B), O19A(H19A)
;
_shelx_res_checksum              79684
_shelx_hkl_checksum              14836
_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 2.250
_oxdiff_exptl_absorpt_empirical_full_min 0.529