Ring closing metathesis reactions of α-methylene-β-lactams: application to the synthesis of a simplified phyllostictine analogue with herbicidal activity.
Coe, Samuel; Pereira, Nicole; Geden, Joanna V.; Clarkson, Guy J.; Fox, David J.; Napier, Richard M.; Neve, Paul; Shipman, Michael; Organic & biomolecular chemistry 13 (2015) 7655–7663; doi:10.1039/c5ob00890e

data_7154525
_publ_section_title
;
 Ring closing metathesis reactions of \a-methylene-\b-lactams: application
 to the synthesis of a simplified phyllostictine analogue with herbicidal
 activity.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7655
_journal_page_last               7663
_journal_paper_doi               10.1039/c5ob00890e
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C19 H25 N O2'
_chemical_formula_sum            'C19 H25 N O2'
_chemical_formula_weight         299.40
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-09 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.442(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.3839(14)
_cell_length_b                   6.2114(3)
_cell_length_c                   25.5110(16)
_cell_measurement_reflns_used    1939
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.89
_cell_measurement_theta_min      3.49
_cell_volume                     3202.8(3)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8160
_diffrn_reflns_theta_full        69.00
_diffrn_reflns_theta_max         70.91
_diffrn_reflns_theta_min         3.49
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSPACK(CrysAlis, Oxford Diffraction)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0979P)^2^+2.5007P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1856
_reflns_number_gt                2467
_reflns_number_total             3030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00890e2.cif
_cod_data_source_block           sc2
_cod_depositor_comments
'Adding full bibliography for 7154525--7154527.cif.'
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7154525