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_4033852
_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 O3, H2 O'
_chemical_formula_sum            'C17 H27 N O4'
_chemical_formula_weight         309.39
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2222(3)
_cell_length_b                   14.2829(4)
_cell_length_c                   17.1194(4)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.20
_cell_measurement_theta_min      3.09
_cell_volume                     3233.02(14)
_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 0.977
_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  0.0328
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20954
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.198
_diffrn_reflns_theta_min         4.031
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.850
_exptl_crystal_size_min          0.840
_exptl_transmission_factor_max   0.3841
_exptl_transmission_factor_min   0.2719
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_coef       0.0108(4)
_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   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         5923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.6905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0755
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                5921
_reflns_number_total             5923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01723_si_003.cif
_cod_data_source_block           cu_fkb16_0m
_cod_database_code               4033852
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.530
_shelx_estimated_absorpt_t_max   0.581
_shelx_res_checksum              71241
_shelx_hkl_checksum              34728