A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon-Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from <i>Kopsia arborea</i>.
Wong, Soon-Kit; Wong, Suet-Pick; Sim, Kae-Shin; Lim, Siew-Huah; Low, Yun-Yee; Kam, Toh-Seok; Journal of natural products 82 (2019) 1902–1907; doi:10.1021/acs.jnatprod.9b00255

data_1552681
_publ_section_title
;
 A Cytotoxic Indole Characterized by Incorporation of a Unique
 Carbon-Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids
 Incorporating a Substituted Tetrahydrofuranone Ring from <i>Kopsia
 arborea</i>.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              1902
_journal_page_last               1907
_journal_paper_doi               10.1021/acs.jnatprod.9b00255
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H22 N2 O4, CH4 O, H2O'
_chemical_formula_sum            'C20 H28 N2 O6'
_chemical_formula_weight         392.44
_chemical_name_common            'Arbophyllinine B'
_chemical_temperature_decomposition_gt 488
_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   mixed
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 101.551(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7413(5)
_cell_length_b                   41.936(4)
_cell_length_c                   6.7867(5)
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    99.8(6)
_cell_measurement_theta_max      30.0770
_cell_measurement_theta_min      4.0420
_cell_volume                     1879.8(3)
_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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.8(6)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.811
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.811
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9424
_diffrn_reflns_point_group_measured_fraction_full 0.796
_diffrn_reflns_point_group_measured_fraction_max 0.638
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.304
_diffrn_reflns_theta_min         2.914
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7210
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0565P)^2^+0.2221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_full    0.611
_reflns_Friedel_fraction_max     0.461
_reflns_number_gt                6117
_reflns_number_total             7210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00255_si_004.cif
_cod_data_source_block           Arbophyllinine_B
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_temperature_decomposition_gt' since the value was
specified as 'more than' ('>') a certain temperature. The value
'>488K dec.' was changed to '488' -- it should be numeric and without
a unit designator.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1552681
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              2405
_shelx_hkl_checksum              87675