Lycopodium Alkaloids: Lycoplatyrine A, an Unusual Lycodine-Piperidine Adduct from Lycopodium platyrhizoma and the Absolute Configurations of Lycoplanine D and Lycogladine H.
Yeap, Joanne Soon-Yee; Lim, Kuan-Hon; Yong, Kien-Thai; Lim, Siew-Huah; Kam, Toh-Seok; Low, Yun-Yee; Journal of natural products 82 (2019) 324–329; doi:10.1021/acs.jnatprod.8b00754

data_1552641
_publ_section_title
;
 Lycopodium Alkaloids: Lycoplatyrine A, an Unusual Lycodine-Piperidine
 Adduct from Lycopodium platyrhizoma and the Absolute Configurations of
 Lycoplanine D and Lycogladine H.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              324
_journal_page_last               329
_journal_paper_doi               10.1021/acs.jnatprod.8b00754
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H23 N O3'
_chemical_formula_sum            'C17 H23 N O3'
_chemical_formula_weight         289.36
_chemical_melting_point          429.0(10)
_chemical_name_common            'lycogladine H'
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.80760(10)
_cell_length_b                   14.3592(2)
_cell_length_c                   15.3172(2)
_cell_measurement_reflns_used    4040
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      74.9540
_cell_measurement_theta_min      4.1900
_cell_volume                     1497.28(4)
_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    '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      160(2)
_diffrn_detector_area_resol_mean 5.2020
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5378
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.426
_diffrn_reflns_theta_min         4.220
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75959
_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    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1167 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0723P)^2^+0.1309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                2909
_reflns_number_total             2998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00754_si_003.cif
_cod_data_source_block           exp_Compound_11
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '428-430 K' was changed to
'429.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1552641
_shelx_shelxl_version_number     2018/1
_shelx_res_checksum              71717
_shelx_hkl_checksum              59325