Phthalideisoquinoline Hemiacetal Alkaloids from <i>Corydalis decumbens</i> That Inhibit Spontaneous Calcium Oscillations, Including Alkyl Derivatives of (+)-Egenine That Are Strikingly Levorotatory.
Zhang, Chun-Lei; Huang, Qi-Long; Chen, Juan; Zhang, Wan-Jin; Jin, Hai-Xiao; Wang, Hong-Bo; Naman, C. Benjamin; Cao, Zheng-Yu; Journal of natural products 82 (2019) 2713–2720; doi:10.1021/acs.jnatprod.9b00247

data_1552591
_publ_section_title
;
 Phthalideisoquinoline Hemiacetal Alkaloids from <i>Corydalis
 decumbens</i> That Inhibit Spontaneous Calcium Oscillations, Including
 Alkyl Derivatives of (+)-Egenine That Are Strikingly Levorotatory.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2713
_journal_page_last               2720
_journal_paper_doi               10.1021/acs.jnatprod.9b00247
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 N O6'
_chemical_formula_sum            'C21 H21 N O6'
_chemical_formula_weight         383.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.670(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2610(9)
_cell_length_b                   6.1061(3)
_cell_length_c                   16.8271(10)
_cell_measurement_reflns_used    4243
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0390
_cell_measurement_theta_min      2.8150
_cell_volume                     1798.40(18)
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_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 0.977
_diffrn_measured_fraction_theta_max 0.957
_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    -66.00  33.00   1.00    1.00    --  -40.98  38.00  90.00   99
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00-120.00  100
  3  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00 -30.00  101
  4  \w     16.00 115.00   1.00    1.00    --   40.98  38.00 -30.00   99
  5  \w      8.00 117.00   1.00    1.00    --   40.98  77.00   0.00  109
  6  \w      8.00 117.00   1.00    1.00    --   40.98  77.00 -30.00  109
  7  \w     34.00 121.00   1.00    3.00    --  106.95-125.00  90.00   87
  8  \w     78.00 178.00   1.00    3.00    --  106.95  61.00 -30.00  100
  9  \w     78.00 178.00   1.00    3.00    --  106.95  61.00 -90.00  100
 10  \w     78.00 178.00   1.00    3.00    --  106.95  61.00   0.00  100
 11  \w     74.00 178.00   1.00    3.00    --  106.95  77.00-150.00  104
 12  \w     74.00 178.00   1.00    3.00    --  106.95  77.00-120.00  104
 13  \w     74.00 105.00   1.00    3.00    --  106.95  77.00 -60.00   31
;
_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      0.0467732000
_diffrn_orient_matrix_UB_12      0.0303721000
_diffrn_orient_matrix_UB_13      0.0991085000
_diffrn_orient_matrix_UB_21      0.0743211000
_diffrn_orient_matrix_UB_22      -0.0381213000
_diffrn_orient_matrix_UB_23      -0.0115279000
_diffrn_orient_matrix_UB_31      0.0057548000
_diffrn_orient_matrix_UB_32      0.2475999000
_diffrn_orient_matrix_UB_33      -0.0138667000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6339
_diffrn_reflns_point_group_measured_fraction_full 0.878
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.429
_diffrn_reflns_theta_min         2.890
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60851
_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    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1111 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0543P)^2^+2.0061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_full    0.755
_reflns_Friedel_fraction_max     0.704
_reflns_number_gt                3019
_reflns_number_total             3072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00247_si_002.cif
_cod_data_source_block           27
_cod_database_code               1552591
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 97.79
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7'(H7'), C1(H1), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C9'(H9'A,H9'B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C2'(H2'), C3'(H3')
2.d Idealised Me refined as rotating group:
 C8'(H8'A,H8'B,H8'C), C11(H11A,H11B,H11C)
;
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.607