Huperserratines A and B, Two Macrocyclic <i>Lycopodium</i> Alkaloids with an Unusual Skeleton from <i>Huperzia serrata</i>.
Wu, Xing-De; Li, Xiao-Nian; Peng, Li-Yan; Zhao, Qin-Shi; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00623

data_4038308
_publ_section_title
;
 Huperserratines A and B, Two Macrocyclic <i>Lycopodium</i> Alkaloids with
 an Unusual Skeleton from <i>Huperzia serrata</i>.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00623
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H28 N2 O3'
_chemical_formula_sum            'C17 H28 N2 O3'
_chemical_formula_weight         308.41
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.8540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4076(3)
_cell_length_b                   6.5798(2)
_cell_length_c                   12.4643(4)
_cell_measurement_reflns_used    7333
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.07
_cell_measurement_theta_min      3.61
_cell_volume                     838.28(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7198
_diffrn_reflns_theta_full        69.54
_diffrn_reflns_theta_max         69.54
_diffrn_reflns_theta_min         3.61
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.6896
_exptl_absorpt_correction_T_min  0.5006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          1.20
_exptl_crystal_size_mid          0.96
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(18)
_refine_ls_extinction_coef       0.128(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.1487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                2554
_reflns_number_total             2555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00623_si_002.cif
_cod_data_source_block           cu_fwa_148_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038308