Alopecuroides A‒E, Matrine-Type Alkaloid Dimers from the Aerial Parts of Sophora alopecuroides
Fan, Chun-Lin; Zhang, Yu-Bo; Chen, Ye; Xie, Pei; Wang, Guo-Cai; Tian, Hai-Yan; Li, Yao-Lan; Huang, Xiao-Jun; Zhang, Xiao-Qi; Li, Zhi-Yong; Liu, Jun-Shan; Ye, Wen-Cai; Chen, Wei-Min; Journal of Natural Products  (2019) –; doi:10.1021/acs.jnatprod.8b01081

data_1552942
_publ_section_title
;
 Alopecuroides A--E, Matrine-Type Alkaloid Dimers from the Aerial Parts of
 Sophora alopecuroides
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.8b01081
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H43 N5 O3, 4(H2 O)'
_chemical_formula_sum            'C31 H51 N5 O7'
_chemical_formula_weight         605.76
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.9421(2)
_cell_length_b                   14.47187(13)
_cell_length_c                   7.75513(6)
_cell_measurement_reflns_used    20033
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4070
_cell_measurement_theta_min      4.3750
_cell_volume                     3135.98(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_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   -129.00  47.00   1.00    1.00    --  -41.11   0.00-120.00  176
  2  \w     23.00  97.00   1.00    1.00    --   41.11-125.00-150.00   74
  3  \w     31.00 140.00   1.00    1.17    --  106.95 -77.00 -30.00  109
  4  \w     78.00 178.00   1.00    1.17    --  106.95  61.00  90.00  100
  5  \w     25.00 160.00   1.00    1.17    --  106.95 -15.00  90.00  135
  6  \w     24.00 109.00   1.00    1.17    --  106.95 -94.00-120.00   85
  7  \w     94.00 178.00   1.00    1.17    --  106.95 125.00 -90.00   84
  8  \w   -116.00 -17.00   1.00    1.00    --  -41.11 -37.00 150.00   99
  9  \w   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00  90.00  108
 10  \w     81.00 178.00   1.00    1.17    --  106.95  45.00-180.00   97
 11  \w     74.00 178.00   1.00    1.17    --  106.95  77.00 -30.00  104
 12  \w     74.00 178.00   1.00    1.17    --  106.95  77.00  30.00  104
 13  \w     79.00 178.00   1.00    1.17    --  106.95  30.00 -90.00   99
 14  \w   -117.00  -9.00   1.00    1.00    --  -41.11 -77.00 -60.00  108
 15  \w     23.00  97.00   1.00    1.00    --   41.11-125.00  30.00   74
 16  \w     74.00 126.00   1.00    1.17    --  106.95  77.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0493206000
_diffrn_orient_matrix_UB_12      0.0460452000
_diffrn_orient_matrix_UB_13      -0.0225276000
_diffrn_orient_matrix_UB_21      0.0149789000
_diffrn_orient_matrix_UB_22      0.0343433000
_diffrn_orient_matrix_UB_23      -0.1801639000
_diffrn_orient_matrix_UB_31      -0.0196051000
_diffrn_orient_matrix_UB_32      -0.0896116000
_diffrn_orient_matrix_UB_33      -0.0805233000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            29910
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.643
_diffrn_reflns_theta_min         3.439
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2523 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0613P)^2^+0.5985P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                6085
_reflns_number_total             6230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            17_23.cif
_cod_data_source_block           17_23
_cod_original_cell_volume        3135.98(5)
_cod_database_code               1552942
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O004(H0AA,H), O005(H1AA,HA), O006(H2AA,HB), O009(H3AA,HC)
2.b Ternary CH refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00L(H00L),
 C00Q(H00Q), C00T(H00T), C00U(H00U), C00W(H00X), C00Z(H00)
2.c Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00B), C00M(H00C,H00D), C00N(H00J,H00K), C00P(H00M,H00N), C00R(H00O,
 H00P), C00S(H00R,H00S), C00V(H00V,H00W), C00X(H00Y,HD), C00Y(H00Z,HE),
 C010(H01A,H01B), C011(H01C,H01D), C013(H01E,H01F), C014(H01G,H01H), C015(H01I,
 H01J), C016(H01K,H01L), C017(H01M,H01N)
;
_shelx_res_checksum              62221
_shelx_hkl_checksum              36081
_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.773