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_7154527
_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         'C38 H50 N2 O6'
_chemical_formula_sum            'C38 H50 N2 O6'
_chemical_formula_weight         630.80
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-06-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2015-02-09 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                100.027(3)
_cell_angle_beta                 98.395(3)
_cell_angle_gamma                104.657(3)
_cell_formula_units_Z            2
_cell_length_a                   8.7440(3)
_cell_length_b                   10.4501(4)
_cell_length_c                   20.1688(6)
_cell_measurement_reflns_used    8287
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.9586
_cell_measurement_theta_min      4.4801
_cell_volume                     1720.44(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_details
;
  1 omega -128.00   44.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6532    0.0000  120.0000 172

  2 omega  -96.00  -31.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6532  125.0000  120.0000 65

  3 omega  -50.00  -24.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6532   38.0000 -180.0000 26

  4 omega   33.00   90.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6532 -125.0000   30.0000 57

  5 omega   28.00   61.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6532 -125.0000  -60.0000 33

  6 omega -139.00 -114.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000  -60.0000 25

  7 omega -125.00  -99.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000 -180.0000 26

  8 omega   31.00  109.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000   90.0000 78

  9 omega   88.00  171.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000   60.0000 83

 10 omega  111.00  177.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   92.0000 -113.0000 66

 11 omega   39.00   95.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000 -180.0000 56

 12 omega   90.00  171.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   30.0000   30.0000 81

 13 omega   48.00  109.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000  -30.0000 61

 14 omega  114.00  178.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000   45.0000  -60.0000 64

 15 omega   63.00   89.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000 -120.0000 26

 16 omega   57.00   98.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000 -150.0000 41

 17 omega   68.00  106.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -94.0000   30.0000 38

 18 omega   38.00   63.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -30.0000   90.0000 25

 19 omega  116.00  161.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  -30.0000 45

 20 omega  117.00  143.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  111.0000  -60.0000 26

 21 omega   41.00   94.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000  -45.0000  -60.0000 53

 22 omega   38.00  115.00   1.0000   56.0000
omega____ theta____ kappa____ phi______ frames
    -      115.0000 -111.0000  -90.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1096268000
_diffrn_orient_matrix_UB_12      -0.0578208000
_diffrn_orient_matrix_UB_13      -0.0717060000
_diffrn_orient_matrix_UB_21      0.0282535000
_diffrn_orient_matrix_UB_22      0.1444157000
_diffrn_orient_matrix_UB_23      -0.0129095000
_diffrn_orient_matrix_UB_31      0.1473854000
_diffrn_orient_matrix_UB_32      -0.0143858000
_diffrn_orient_matrix_UB_33      -0.0309481000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12402
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.184
_diffrn_reflns_theta_min         4.484
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0704P)^2^+0.2850P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6483
_reflns_number_total             7138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00890e2.cif
_cod_data_source_block           sc6
_cod_depositor_comments
'Adding full bibliography for 7154525--7154527.cif.'
_cod_original_cell_volume        1720.46(10)
_cod_database_code               7154527
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C27(H27A,H27B),
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B),
  C33(H33A,H33B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C22(H22), C36(H36), C37(H37), C38(H38),
 C40(H40), C41(H41)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C44(H44A,H44B,H44C)
;
_shelxl_version_number           2013-2