LC-MS-Guided Isolation of Insulin-Secretion-Promoting Monoterpenoid Carbazole Alkaloids from Murraya microphylla.
Ma, Xiao-Li; Li, Jun; Zheng, Jiao; Gu, Xiao-Pan; Ferreira, Daneel; Zjawiony, Jordan K.; Zhao, Ming-Bo; Guo, Xiao-Yu; Tu, Peng-Fei; Jiang, Yong; Journal of natural products 81 (2018) 2371–2380; doi:10.1021/acs.jnatprod.8b00338

data_1553380
_publ_section_title
;
 LC-MS-Guided Isolation of Insulin-Secretion-Promoting Monoterpenoid
 Carbazole Alkaloids from Murraya microphylla.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2371
_journal_page_last               2380
_journal_paper_doi               10.1021/acs.jnatprod.8b00338
_journal_volume                  81
_journal_year                    2018
_chemical_formula_moiety         'C29 H35 N O3'
_chemical_formula_sum            'C29 H35 N O3'
_chemical_formula_weight         445.58
_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             2016-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9454(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.72842(7)
_cell_length_b                   10.28179(10)
_cell_length_c                   15.30230(15)
_cell_measurement_reflns_used    16019
_cell_measurement_temperature    120
_cell_measurement_theta_max      68.9470
_cell_measurement_theta_min      2.8610
_cell_volume                     1215.25(2)
_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      120
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.982
_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  75.00   1.00    1.00    --    0.00   0.00   0.00  165
  2  \w    -90.00  60.00   1.00    1.00    --    0.00  45.00   0.00  150
  3  \w   -135.00  45.00   1.00    1.00    --  -45.00   0.00 320.00  180
  4  \w   -135.00  36.00   1.00    1.00    --  -45.00  55.00 200.00  171
  5  \w   -135.00  21.00   1.00    1.00    --  -45.00  30.00 120.00  156
  6  \w   -135.00  15.00   1.00    1.00    --  -45.00  55.00 280.00  150
  7  \w   -135.00  45.00   1.00    1.00    --  -45.00  55.00  40.00  180
  8  \w   -180.00   0.00   1.00    3.00    --  -90.00  55.00 200.00  180
  9  \w   -180.00   0.00   1.00    3.00    --  -90.00  30.00   0.00  180
 10  \w   -180.00  -9.00   1.00    3.00    --  -90.00  45.00 240.00  171
 11  \w   -180.00   0.00   1.00    3.00    --  -90.00  55.00 160.00  180
 12  \w   -180.00   0.00   1.00    3.00    --  -90.00  45.00  40.00  180
 13  \w   -180.00 -72.00   1.00    3.00    --  -90.00  55.00 240.00  108
 14  \w   -127.00 -77.00   1.00    3.00    --  -90.00   0.00 160.00   50
;
_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      -0.1409426000
_diffrn_orient_matrix_UB_12      -0.0943461000
_diffrn_orient_matrix_UB_13      -0.0350473000
_diffrn_orient_matrix_UB_21      0.1203062000
_diffrn_orient_matrix_UB_22      -0.0443484000
_diffrn_orient_matrix_UB_23      -0.0724827000
_diffrn_orient_matrix_UB_31      0.0737483000
_diffrn_orient_matrix_UB_32      -0.1075962000
_diffrn_orient_matrix_UB_33      0.0605698000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18514
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.755
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90014
_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 yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0300P)^2^+0.8600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                4006
_reflns_number_total             4348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00338_si_002.cif
_cod_data_source_block           mc-b-1-c-2-a-t15-a
_cod_database_code               1553380
_reflns_odcompleteness_completeness 98.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.63
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12'(H12'), C14'(H14')
2.b Secondary CH2 refined with riding coordinates:
 C9'(H9'A,H9'B), C10'(H10A,H10B), C11'(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N9(H9), C1'(H1'), C2'(H2'), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C), C6'(H6'A,H6'B,H6'C), C7'(H7'A,H7'B,
 H7'C), C15'(H15A,H15B,H15C), C16'(H16A,H16B,H16C), C17'(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              76192
_shelx_hkl_checksum              68507
_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.663