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_1547853
_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_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 N2 O, 0.5(H2 O), 0.5(C H4 O)'
_chemical_formula_sum            'C19.5 H27 N2 O2'
_chemical_formula_weight         321.43
_chemical_melting_point          387.0(10)
_chemical_name_common            (-)-Eburnamine
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                89.964(3)
_cell_angle_beta                 78.459(3)
_cell_angle_gamma                76.610(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0112(3)
_cell_length_b                   9.8045(5)
_cell_length_c                   10.2163(4)
_cell_measurement_reflns_used    4962
_cell_measurement_temperature    145(1)
_cell_measurement_theta_max      73.4610
_cell_measurement_theta_min      6.0400
_cell_volume                     859.33(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'enCIFer (Allen, et. al., J. Applied Cryst., 37, 335-338, 2004)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      145(1)
_diffrn_detector_area_resol_mean 5.2020
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_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  0.0126
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5830
_diffrn_reflns_point_group_measured_fraction_full 0.584
_diffrn_reflns_point_group_measured_fraction_max 0.560
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.625
_diffrn_reflns_theta_min         4.422
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 519 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0561P)^2^+0.1159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.161
_reflns_Friedel_fraction_full    0.172
_reflns_Friedel_fraction_max     0.156
_reflns_number_gt                3848
_reflns_number_total             3899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00621_si_002.cif
_cod_data_source_block           exp_6115
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '386-388 K' was changed to
'387.0(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.

2019-03-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C39 H54 N4 O4'
_cod_original_formula_sum        'C39 H54 N4 O4'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     642.86
_cod_database_code               1547853
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              78876
_shelx_hkl_checksum              8273