Aspidofractinine and Eburnane Alkaloids from a North Borneo Kopsia. Ring-Contracted, Additional Ring-Fused, and Paucidactine-Type Aspidofractinine Alkaloids from K. pauciflora.
Yap, Wai-Sum; Gan, Chew-Yan; Sim, Kae-Shin; Lim, Siew-Huah; Low, Yun-Yee; Kam, Toh-Seok; Journal of natural products 79 (2016) 230–239; doi:10.1021/acs.jnatprod.5b00992

data_1540726
_publ_section_title
;
 Aspidofractinine and Eburnane Alkaloids from a North Borneo Kopsia.
 Ring-Contracted, Additional Ring-Fused, and Paucidactine-Type
 Aspidofractinine Alkaloids from K. pauciflora.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              230
_journal_page_last               239
_journal_paper_doi               10.1021/acs.jnatprod.5b00992
_journal_volume                  79
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H22 N2 O'
_chemical_formula_weight         294.38
_chemical_melting_point          436.0(10)
_chemical_name_common            (-)-19(R)-hydroxyeburnamenine
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.4100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.63910(10)
_cell_length_b                   7.92600(10)
_cell_length_c                   11.5438(2)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.38
_cell_volume                     781.945(19)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6701
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.005
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         1.783
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER, 2006)'
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1130 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0476P)^2^+0.1188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                2942
_reflns_number_total             3386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np5b00992_si_005.cif
_cod_data_source_block           minus-19R-hydroxyeburnamenine
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '435-437' was changed to '436.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1540726--1540731.cif.
;
_cod_database_code               1540726
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              42014
_shelx_hkl_checksum              45313