#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023928.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023928
loop_
_publ_author_name
'Claire C. A. Cariou'
'Guy J. Clarkson'
'Michael Shipman'
_publ_contact_author_address
;
Department of Chemistry
University of Warwick
Gibbethill Road
Coventry
CV4 7AL
UK
;
_publ_contact_author_email       m.shipman@warwick.ac.uk
_publ_contact_author_name        'Michael Shipman'
_publ_contact_author_phone       '024 765 23186'
_publ_section_title
;
 Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from
 Methyleneaziridines Using a Four-Component Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9762
_journal_page_last               9764
_journal_paper_doi               10.1021/jo801664g
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C34 H35 N O3'
_chemical_formula_weight         505.63
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.709(2)
_cell_angle_beta                 99.009(2)
_cell_angle_gamma                112.083(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7661(3)
_cell_length_b                   11.6217(3)
_cell_length_c                   14.3084(4)
_cell_measurement_reflns_used    30507
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.91
_cell_volume                     1375.72(8)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_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      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29928
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        nil
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0466
_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/[σ²(Fo²)+(0.0549P)²+0.3974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                4937
_reflns_number_total             6292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801664g_si_001.cif
_cod_data_source_block           cc3(2a)
_cod_database_code               4023928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.30344(19) 0.00923(15) -0.01391(13) 0.0381(4) Uani 1 1 d . . .
H1A H 1.3476 -0.0308 -0.0634 0.057 Uiso 1 1 calc R . .
H1B H 1.1928 -0.0229 -0.0462 0.057 Uiso 1 1 calc R . .
H1C H 1.3170 -0.0165 0.0451 0.057 Uiso 1 1 calc R . .
O2 O 1.38048(12) 0.15188(10) 0.01912(8) 0.0342(2) Uani 1 1 d . . .
C3 C 1.32787(15) 0.22372(14) 0.08507(10) 0.0268(3) Uani 1 1 d . . .
C4 C 1.39809(16) 0.36189(14) 0.11031(11) 0.0300(3) Uani 1 1 d . . .
H4A H 1.4720 0.3997 0.0784 0.036 Uiso 1 1 calc R . .
C5 C 1.36064(16) 0.44411(14) 0.18157(11) 0.0296(3) Uani 1 1 d . . .
H5A H 1.4098 0.5382 0.1985 0.036 Uiso 1 1 calc R . .
C6 C 1.25181(15) 0.39142(13) 0.22924(10) 0.0268(3) Uani 1 1 d . . .
C7 C 1.17856(16) 0.25293(13) 0.20046(11) 0.0276(3) Uani 1 1 d . . .
H7A H 1.1018 0.2149 0.2305 0.033 Uiso 1 1 calc R . .
C8 C 1.21485(16) 0.16869(13) 0.12878(11) 0.0280(3) Uani 1 1 d . . .
H8A H 1.1628 0.0743 0.1098 0.034 Uiso 1 1 calc R . .
C9 C 1.22427(16) 0.48545(14) 0.31397(11) 0.0306(3) Uani 1 1 d . . .
H9A H 1.2985 0.5083 0.3798 0.037 Uiso 1 1 calc R . .
H9B H 1.2462 0.5696 0.3021 0.037 Uiso 1 1 calc R . .
N10 N 1.06897(13) 0.43165(11) 0.32251(9) 0.0261(2) Uani 1 1 d . . .
O11 O 1.06775(13) 0.33543(11) 0.44611(8) 0.0385(3) Uani 1 1 d . . .
C11 C 1.01085(16) 0.37086(13) 0.38462(10) 0.0278(3) Uani 1 1 d . . .
C12 C 0.85324(16) 0.36811(13) 0.34769(10) 0.0256(3) Uani 1 1 d . . .
H12A H 0.8302 0.4278 0.4021 0.031 Uiso 1 1 calc R . .
C13 C 0.92519(15) 0.43789(12) 0.27569(10) 0.0235(3) Uani 1 1 d . . .
C14 C 0.95019(15) 0.58293(12) 0.30345(10) 0.0252(3) Uani 1 1 d . . .
H14A H 1.0004 0.6323 0.3780 0.030 Uiso 1 1 calc R . .
H14B H 1.0212 0.6261 0.2682 0.030 Uiso 1 1 calc R . .
C15 C 0.79982(16) 0.59385(13) 0.27425(12) 0.0306(3) Uani 1 1 d . . .
H15A H 0.7403 0.5302 0.2031 0.037 Uiso 1 1 calc R . .
H15B H 0.7374 0.5658 0.3190 0.037 Uiso 1 1 calc R . .
C16 C 0.82023(16) 0.73181(13) 0.28199(10) 0.0261(3) Uani 1 1 d . . .
C17 C 0.93518(17) 0.84783(14) 0.36086(11) 0.0306(3) Uani 1 1 d . . .
H17A H 1.0044 0.8408 0.4111 0.037 Uiso 1 1 calc R . .
C18 C 0.94993(19) 0.97408(15) 0.36694(12) 0.0361(3) Uani 1 1 d . . .
H18A H 1.0294 1.0524 0.4208 0.043 Uiso 1 1 calc R . .
C19 C 0.84898(19) 0.98549(15) 0.29473(12) 0.0372(4) Uani 1 1 d . . .
H19A H 0.8577 1.0713 0.2995 0.045 Uiso 1 1 calc R . .
C20 C 0.73548(18) 0.87129(16) 0.21574(12) 0.0359(3) Uani 1 1 d . . .
H20A H 0.6660 0.8785 0.1659 0.043 Uiso 1 1 calc R . .
C21 C 0.72280(16) 0.74609(15) 0.20904(11) 0.0306(3) Uani 1 1 d . . .
H21A H 0.6459 0.6684 0.1534 0.037 Uiso 1 1 calc R . .
C22 C 0.85223(16) 0.34975(13) 0.16201(10) 0.0245(3) Uani 1 1 d . . .
H22A H 0.7405 0.3264 0.1434 0.029 Uiso 1 1 calc R . .
H22B H 0.8617 0.2652 0.1502 0.029 Uiso 1 1 calc R . .
C23 C 0.92405(17) 0.41428(13) 0.09085(10) 0.0283(3) Uani 1 1 d . . .
H23A H 0.8964 0.4881 0.0914 0.034 Uiso 1 1 calc R . .
H23B H 1.0382 0.4532 0.1167 0.034 Uiso 1 1 calc R . .
C24 C 0.86890(15) 0.31389(13) -0.01757(10) 0.0256(3) Uani 1 1 d . . .
C25 C 0.96015(16) 0.25481(13) -0.05374(10) 0.0270(3) Uani 1 1 d . . .
H25A H 1.0588 0.2794 -0.0100 0.032 Uiso 1 1 calc R . .
C26 C 0.90979(16) 0.16062(14) -0.15249(11) 0.0294(3) Uani 1 1 d . . .
H26A H 0.9741 0.1218 -0.1759 0.035 Uiso 1 1 calc R . .
C27 C 0.76606(17) 0.12308(16) -0.21687(11) 0.0354(3) Uani 1 1 d . . .
H27A H 0.7311 0.0581 -0.2843 0.043 Uiso 1 1 calc R . .
C28 C 0.67331(18) 0.18071(18) -0.18252(12) 0.0399(4) Uani 1 1 d . . .
H28A H 0.5747 0.1555 -0.2266 0.048 Uiso 1 1 calc R . .
C29 C 0.72450(17) 0.27566(16) -0.08339(11) 0.0342(3) Uani 1 1 d . . .
H29A H 0.6603 0.3148 -0.0604 0.041 Uiso 1 1 calc R . .
O30 O 0.73234(11) 0.23747(9) 0.29999(7) 0.0300(2) Uani 1 1 d . . .
C31 C 0.58244(17) 0.23085(15) 0.29688(11) 0.0326(3) Uani 1 1 d . . .
H31A H 0.5039 0.1483 0.2395 0.039 Uiso 1 1 calc R . .
H31B H 0.5781 0.3085 0.2834 0.039 Uiso 1 1 calc R . .
C32 C 0.54215(16) 0.23088(13) 0.39467(11) 0.0288(3) Uani 1 1 d . . .
C33 C 0.43339(18) 0.27453(17) 0.42039(13) 0.0414(4) Uani 1 1 d . . .
H33A H 0.3944 0.3148 0.3808 0.050 Uiso 1 1 calc R . .
C34 C 0.38120(19) 0.25987(19) 0.50346(13) 0.0489(5) Uani 1 1 d . . .
H34A H 0.3051 0.2880 0.5193 0.059 Uiso 1 1 calc R . .
C35 C 0.43978(19) 0.20486(17) 0.56227(12) 0.0448(4) Uani 1 1 d . . .
H35A H 0.4033 0.1936 0.6183 0.054 Uiso 1 1 calc R . .
C36 C 0.5517(2) 0.16596(15) 0.53995(12) 0.0394(4) Uani 1 1 d . . .
H36A H 0.5943 0.1303 0.5820 0.047 Uiso 1 1 calc R . .
C37 C 0.60286(18) 0.17848(14) 0.45654(11) 0.0330(3) Uani 1 1 d . . .
H37A H 0.6798 0.1510 0.4418 0.040 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 O2 C1 117.14(11) . . ?
O2 C3 C8 124.69(12) . . ?
O2 C3 C4 115.79(12) . . ?
C8 C3 C4 119.50(12) . . ?
C5 C4 C3 120.21(12) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 121.18(12) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C7 C6 C5 117.91(12) . . ?
C7 C6 C9 122.29(12) . . ?
C5 C6 C9 119.69(12) . . ?
C6 C7 C8 121.61(12) . . ?
C6 C7 H7A 119.2 . . ?
C8 C7 H7A 119.2 . . ?
C7 C8 C3 119.50(12) . . ?
C7 C8 H8A 120.3 . . ?
C3 C8 H8A 120.3 . . ?
N10 C9 C6 114.37(11) . . ?
N10 C9 H9A 108.7 . . ?
C6 C9 H9A 108.7 . . ?
N10 C9 H9B 108.7 . . ?
C6 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 N10 C9 130.89(12) . . ?
C11 N10 C13 96.41(10) . . ?
C9 N10 C13 132.37(11) . . ?
O11 C11 N10 132.06(14) . . ?
O11 C11 C12 135.75(13) . . ?
N10 C11 C12 92.19(10) . . ?
O30 C12 C11 112.85(11) . . ?
O30 C12 C13 116.92(10) . . ?
C11 C12 C13 86.16(10) . . ?
O30 C12 H12A 112.8 . . ?
C11 C12 H12A 112.8 . . ?
C13 C12 H12A 112.8 . . ?
N10 C13 C22 113.18(10) . . ?
N10 C13 C14 111.19(10) . . ?
C22 C13 C14 115.08(11) . . ?
N10 C13 C12 85.23(9) . . ?
C22 C13 C12 113.78(10) . . ?
C14 C13 C12 114.82(10) . . ?
C15 C14 C13 112.82(11) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 114.88(11) . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C21 C16 C17 117.96(13) . . ?
C21 C16 C15 119.99(12) . . ?
C17 C16 C15 122.05(13) . . ?
C16 C17 C18 120.81(14) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C19 C18 C17 120.12(14) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C20 C19 C18 119.57(13) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 120.11(14) . . ?
C19 C20 H20A 119.9 . . ?
C21 C20 H20A 119.9 . . ?
C20 C21 C16 121.39(14) . . ?
C20 C21 H21A 119.3 . . ?
C16 C21 H21A 119.3 . . ?
C13 C22 C23 114.56(11) . . ?
C13 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C13 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 111.86(11) . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C29 118.13(13) . . ?
C25 C24 C23 120.58(12) . . ?
C29 C24 C23 121.28(12) . . ?
C26 C25 C24 121.22(13) . . ?
C26 C25 H25A 119.4 . . ?
C24 C25 H25A 119.4 . . ?
C27 C26 C25 120.11(13) . . ?
C27 C26 H26A 119.9 . . ?
C25 C26 H26A 119.9 . . ?
C26 C27 C28 119.67(14) . . ?
C26 C27 H27A 120.2 . . ?
C28 C27 H27A 120.2 . . ?
C27 C28 C29 120.07(14) . . ?
C27 C28 H28A 120.0 . . ?
C29 C28 H28A 120.0 . . ?
C28 C29 C24 120.81(13) . . ?
C28 C29 H29A 119.6 . . ?
C24 C29 H29A 119.6 . . ?
C12 O30 C31 113.72(10) . . ?
O30 C31 C32 113.21(11) . . ?
O30 C31 H31A 108.9 . . ?
C32 C31 H31A 108.9 . . ?
O30 C31 H31B 108.9 . . ?
C32 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C37 C32 C33 118.47(13) . . ?
C37 C32 C31 121.15(13) . . ?
C33 C32 C31 120.20(13) . . ?
C32 C33 C34 120.76(16) . . ?
C32 C33 H33A 119.6 . . ?
C34 C33 H33A 119.6 . . ?
C35 C34 C33 119.90(15) . . ?
C35 C34 H34A 120.1 . . ?
C33 C34 H34A 120.1 . . ?
C34 C35 C36 119.89(15) . . ?
C34 C35 H35A 120.1 . . ?
C36 C35 H35A 120.1 . . ?
C35 C36 C37 120.59(15) . . ?
C35 C36 H36A 119.7 . . ?
C37 C36 H36A 119.7 . . ?
C32 C37 C36 120.31(14) . . ?
C32 C37 H37A 119.8 . . ?
C36 C37 H37A 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.4276(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O2 C3 1.3686(16) . ?
C3 C8 1.3905(19) . ?
C3 C4 1.3929(19) . ?
C4 C5 1.380(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3957(19) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3901(19) . ?
C6 C9 1.5157(19) . ?
C7 C8 1.3904(19) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 N10 1.4475(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N10 C11 1.3523(17) . ?
N10 C13 1.4952(17) . ?
O11 C11 1.2164(17) . ?
C11 C12 1.532(2) . ?
C12 O30 1.4031(15) . ?
C12 C13 1.5784(18) . ?
C12 H12A 1.0000 . ?
C13 C22 1.5273(18) . ?
C13 C14 1.5277(17) . ?
C14 C15 1.5250(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5077(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.389(2) . ?
C16 C17 1.394(2) . ?
C17 C18 1.395(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.384(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.381(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.387(2) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 C23 1.5357(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5110(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.3906(19) . ?
C24 C29 1.395(2) . ?
C25 C26 1.387(2) . ?
C25 H25A 0.9500 . ?
C26 C27 1.383(2) . ?
C26 H26A 0.9500 . ?
C27 C28 1.385(2) . ?
C27 H27A 0.9500 . ?
C28 C29 1.394(2) . ?
C28 H28A 0.9500 . ?
C29 H29A 0.9500 . ?
O30 C31 1.4297(17) . ?
C31 C32 1.5116(19) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C37 1.387(2) . ?
C32 C33 1.393(2) . ?
C33 C34 1.394(2) . ?
C33 H33A 0.9500 . ?
C34 C35 1.370(3) . ?
C34 H34A 0.9500 . ?
C35 C36 1.378(2) . ?
C35 H35A 0.9500 . ?
C36 C37 1.388(2) . ?
C36 H36A 0.9500 . ?
C37 H37A 0.9500 . ?
