Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia.
Chong, Kam-Weng; Yeap, Joanne Soon-Yee; Lim, Siew-Huah; Weber, Jean-Frédéric F; Low, Yun-Yee; Kam, Toh-Seok; Journal of natural products 80 (2017) 3014–3024; doi:10.1021/acs.jnatprod.7b00621

data_1547851
_publ_section_title
;
 Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              3014
_journal_page_last               3024
_journal_paper_doi               10.1021/acs.jnatprod.7b00621
_journal_volume                  80
_journal_year                    2017
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.38
_chemical_melting_point          468.0(10)
_chemical_name_common            Eburnamonine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.262(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0178(4)
_cell_length_b                   10.4563(4)
_cell_length_c                   16.4936(9)
_cell_measurement_reflns_used    3425
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.2350
_cell_measurement_theta_min      4.9820
_cell_volume                     1519.75(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -54.00  11.00   1.00    1.00    --  -42.00  37.00 -30.00   65
  2  \w    -58.00  -6.00   1.00    1.00    --  -42.00 125.00  90.00   52
  3  \w   -106.00 -19.00   1.00    1.00    --  -42.00 -37.00 -90.00   87
  4  \w      2.00  83.00   1.00    1.00    --   42.00 -99.00-120.00   81
  5  \w     63.00 109.00   1.00    2.35    --  107.31 -94.00 -30.00   46
  6  \w     52.00 121.00   1.00    2.35    --  107.31-125.00  60.00   69
  7  \w     70.00 108.00   1.00    2.35    --  107.31 -94.00 120.00   38
  8  \w     48.00 131.00   1.00    2.35    --  107.31 -45.00  60.00   83
  9  \w     94.00 178.00   1.00    2.35    --  107.31  45.00  60.00   84
 10  \w    106.00 132.00   1.00    2.35    --  107.31 111.00 -42.00   26
 11  \w    101.00 173.00   1.00    2.35    --  107.31  77.00   0.00   72
 12  \w     47.00  88.00   1.00    2.35    --  107.31 -94.00 -60.00   41
 13  \w     47.00  76.00   1.00    2.35    --  107.31-125.00 -60.00   29
 14  \w     43.00 104.00   1.00    2.35    --  107.31 -94.00-150.00   61
 15  \w     40.00 131.00   1.00    2.35    --  107.31 -30.00-120.00   91
 16  \w     31.00  86.00   1.00    2.35    --  107.31 -77.00  60.00   55
 17  \w     30.00 112.00   1.00    2.35    --  107.31 -15.00 -30.00   82
 18  \w   -109.00 -25.00   1.00    1.00    --  -42.00 -37.00   0.00   84
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10564
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.395
_diffrn_reflns_theta_min         5.042
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.2481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2448
_reflns_number_total             3055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00621_si_009.cif
_cod_data_source_block           exp_5908
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '467-469 K' was changed to
'468.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1547851--1547858.cif.
;
_cod_original_cell_volume        1519.74(12)
_cod_database_code               1547851
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              14485
_shelx_hkl_checksum              49762