Phlegmadine A: A <i>Lycopodium</i> Alkaloid with a Unique Cyclobutane Ring from <i>Phlegmariurus phlegmaria</i>.
Zhang, Zhi-Jun; Wang, Chen; Wu, Xing-De; Huang, Yan; Zhou, Wen-Xia; Zhao, Qin-Shi; The Journal of organic chemistry 84 (2019) 11301–11305; doi:10.1021/acs.joc.9b01723

data_4033851
_publ_section_title
;
 Phlegmadine A: A <i>Lycopodium</i> Alkaloid with a Unique Cyclobutane
 Ring from <i>Phlegmariurus phlegmaria</i>.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11301
_journal_page_last               11305
_journal_paper_doi               10.1021/acs.joc.9b01723
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H25 N O2'
_chemical_formula_sum            'C17 H25 N O2'
_chemical_formula_weight         275.38
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.7710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4961(2)
_cell_length_b                   7.4595(2)
_cell_length_c                   13.2851(3)
_cell_measurement_reflns_used    6691
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.39
_cell_measurement_theta_min      3.44
_cell_volume                     718.32(3)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6749
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.388
_diffrn_reflns_theta_min         3.440
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          1.100
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.130
_exptl_transmission_factor_max   0.3843
_exptl_transmission_factor_min   0.2171
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(6)
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.1709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.841
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                2466
_reflns_number_total             2475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01723_si_002.cif
_cod_data_source_block           cu_fkb35_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4033851
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.536
_shelx_estimated_absorpt_t_max   0.921
_shelx_res_checksum              10910
_shelx_hkl_checksum              89120