Vitepyrroloids A-D, 2-Cyanopyrrole-Containing Labdane Diterpenoid Alkaloids from the Leaves of Vitex trifolia.
Luo, Pan; Xia, Wenjuan; Morris-Natschke, Susan L; Lee, Kuo-Hsiung; Zhao, Yu; Gu, Qiong; Xu, Jun; Journal of natural products 80 (2017) 1679–1683; doi:10.1021/acs.jnatprod.6b01195

data_1546201
_publ_section_title
;
 Vitepyrroloids A-D, 2-Cyanopyrrole-Containing Labdane Diterpenoid
 Alkaloids from the Leaves of Vitex trifolia.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1679
_journal_page_last               1683
_journal_paper_doi               10.1021/acs.jnatprod.6b01195
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H32 N2 O'
_chemical_formula_sum            'C21 H32 N2 O'
_chemical_formula_weight         328.50
_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'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.45094(6)
_cell_length_b                   9.21543(8)
_cell_length_c                   26.7264(2)
_cell_measurement_reflns_used    12690
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      72.2590
_cell_measurement_theta_min      3.2990
_cell_volume                     1835.13(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9846
_diffrn_measured_fraction_theta_max 0.9846
_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   -126.00 -79.00   1.00    3.00    --  -44.40 -99.00 -90.00   47
  2  \w   -126.00 -79.00   1.00    3.00    --  -44.40 -99.00   0.00   47
  3  \w     19.00 114.00   1.00    3.00    --   44.40  57.00 -60.00   95
  4  \w     73.00 118.00   1.00    3.00    --   44.40 125.00  30.00   45
  5  \w     73.00 118.00   1.00    3.00    --   44.40 125.00  60.00   45
  6  \w     76.00 171.00   1.00    8.00    --  100.00  45.00-150.00   95
  7  \w     68.00 174.00   1.00    8.00    --  100.00  77.00-120.00  106
  8  \w     17.00 109.00   1.00    8.00    --  100.00 -94.00 120.00   92
  9  \w     68.00 174.00   1.00    8.00    --  100.00  77.00 -60.00  106
 10  \w     17.00 109.00   1.00    8.00    --  100.00 -94.00 -60.00   92
 11  \w     73.00 173.00   1.00    8.00    --  100.00  30.00 -60.00  100
 12  \w     26.00 121.00   1.00    8.00    --  100.00-125.00 -90.00   95
 13  \w     29.00 124.00   1.00    8.00    --  100.00 -45.00-150.00   95
 14  \w     78.00 173.00   1.00    8.00    --  100.00  30.00 120.00   95
 15  \w     78.00 140.00   1.00    8.00    --  100.00  45.00-180.00   62
 16  \w     58.00  84.00   1.00    8.00    --  100.00 -94.00  30.00   26
 17  \w     26.00 120.00   1.00    8.00    --  100.00-125.00 -60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1588724000
_diffrn_orient_matrix_UB_12      0.0818785000
_diffrn_orient_matrix_UB_13      -0.0237385000
_diffrn_orient_matrix_UB_21      -0.1241156000
_diffrn_orient_matrix_UB_22      -0.0547941000
_diffrn_orient_matrix_UB_23      0.0420427000
_diffrn_orient_matrix_UB_31      0.0459392000
_diffrn_orient_matrix_UB_32      0.1350158000
_diffrn_orient_matrix_UB_33      0.0315012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13373
_diffrn_reflns_theta_full        72.2345
_diffrn_reflns_theta_max         72.23
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.1889
_exptl_crystal_description       block
_exptl_crystal_F_000             721.9652
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.2391
_refine_diff_density_min         -0.1393
_refine_diff_density_rms         0.0355
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_d_res_high            0.8095
_refine_ls_d_res_low             13.3632
_refine_ls_goodness_of_fit_ref   1.0500
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    49
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0500
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.3990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.982
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              32
_reflns_limit_l_min              -32
_reflns_number_gt                3563
_reflns_number_total             3577
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            np6b01195_si_002.cif
_cod_data_source_block           lp_mjy-zh_160822
_cod_original_cell_volume        1835.14(3)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1546201
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C2(H2), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C9(H9a,H9b), C10(H10a,H10b), C14(H14a,H14b), C15(H15a,H15b),
 C17(H17a,H17b), C20(H20a,H20b)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C13(H13), C24(H24)
2.d Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C18(H18a,H18b,H18c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 2.489
_oxdiff_exptl_absorpt_empirical_full_min 0.637