#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:42:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178820 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/74/4107456.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_4107456
loop_
_publ_author_name
'Annette D. Allen'
'Jazmin Godoy'
'Nanyan Fu'
'Michelle Nagy'
'Sandra Spadaro'
'Thomas T. Tidwell'
'Sinisa Vukovic'
_publ_section_title
;
 Spiro-Aziridine and Bislactam Formation from Bisketene-Imine
 Cycloadditions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2386
_journal_page_last               2387
_journal_paper_doi               10.1021/ja077623y
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C36 H28 N2 O2'
_chemical_formula_sum            'C36 H28 N2 O2'
_chemical_formula_weight         520.60
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.395(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0203(6)
_cell_length_b                   14.2539(10)
_cell_length_c                   17.3967(11)
_cell_measurement_reflns_used    8839
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     2678.8(3)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.1'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8839
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0493
_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)+(0.0647P)²+0.3916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1323
_reflns_number_gt                1950
_reflns_number_total             3066
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja077623y-file003.cif
_cod_data_source_block           k07233
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4107456
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O1 O 0.15450(11) 0.24659(8) 0.25692(7) 0.0373(3) Uani 1 1 d .
N1 N 0.21063(12) 0.31148(9) 0.14398(8) 0.0278(3) Uani 1 1 d .
C1 C 0.22714(15) 0.26972(11) 0.21652(10) 0.0276(4) Uani 1 1 d .
C2 C 0.36696(14) 0.26705(11) 0.22482(9) 0.0263(4) Uani 1 1 d .
H2A H 0.4068 0.3158 0.2630 0.032 Uiso 1 1 calc R
C3 C 0.34307(14) 0.30684(11) 0.13881(9) 0.0259(4) Uani 1 1 d .
H3A H 0.3575 0.2576 0.1007 0.031 Uiso 1 1 calc R
C4 C 0.43495(14) 0.17515(12) 0.23993(9) 0.0256(4) Uani 1 1 d .
C5 C 0.37217(16) 0.09000(12) 0.23137(10) 0.0304(4) Uani 1 1 d .
H5 H 0.2843 0.0896 0.2188 0.037 Uiso 1 1 calc R
C6 C 0.43599(16) 0.00582(12) 0.24088(11) 0.0337(4) Uani 1 1 d .
H6 H 0.3920 -0.0519 0.2349 0.040 Uiso 1 1 calc R
C7 C 0.10391(14) 0.33299(11) 0.08694(10) 0.0271(4) Uani 1 1 d .
C8 C -0.01316(15) 0.31535(12) 0.10274(11) 0.0326(4) Uani 1 1 d .
H8A H -0.0218 0.2911 0.1523 0.039 Uiso 1 1 calc R
C9 C -0.11675(16) 0.33360(13) 0.04528(12) 0.0409(5) Uani 1 1 d .
H9A H -0.1968 0.3206 0.0552 0.049 Uiso 1 1 calc R
C10 C -0.10488(17) 0.37054(13) -0.02650(12) 0.0430(5) Uani 1 1 d .
H10A H -0.1765 0.3825 -0.0656 0.052 Uiso 1 1 calc R
C11 C 0.01061(17) 0.38985(13) -0.04109(11) 0.0388(5) Uani 1 1 d .
H11A H 0.0185 0.4162 -0.0900 0.047 Uiso 1 1 calc R
C12 C 0.11644(15) 0.37090(12) 0.01561(10) 0.0312(4) Uani 1 1 d .
H12A H 0.1963 0.3839 0.0053 0.037 Uiso 1 1 calc R
C13 C 0.40800(14) 0.39640(11) 0.12655(9) 0.0261(4) Uani 1 1 d .
C14 C 0.51162(15) 0.39311(12) 0.09242(10) 0.0326(4) Uani 1 1 d .
H14A H 0.5355 0.3353 0.0726 0.039 Uiso 1 1 calc R
C15 C 0.58067(17) 0.47347(13) 0.08697(11) 0.0384(5) Uani 1 1 d .
H15A H 0.6523 0.4704 0.0643 0.046 Uiso 1 1 calc R
C16 C 0.54497(16) 0.55770(13) 0.11450(11) 0.0370(4) Uani 1 1 d .
H16A H 0.5920 0.6128 0.1108 0.044 Uiso 1 1 calc R
C17 C 0.44080(17) 0.56213(12) 0.14746(11) 0.0373(4) Uani 1 1 d .
H17A H 0.4155 0.6204 0.1656 0.045 Uiso 1 1 calc R
C18 C 0.37344(16) 0.48179(12) 0.15396(10) 0.0327(4) Uani 1 1 d .
H18A H 0.3027 0.4850 0.1774 0.039 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
C1 N1 C7 132.76(13) . .
C1 N1 C3 94.76(12) . .
C7 N1 C3 131.28(13) . .
O1 C1 N1 131.92(15) . .
O1 C1 C2 135.44(16) . .
N1 C1 C2 92.63(12) . .
C4 C2 C1 119.90(13) . .
C4 C2 C3 117.62(13) . .
C1 C2 C3 85.68(12) . .
N1 C3 C13 118.32(13) . .
N1 C3 C2 86.57(11) . .
C13 C3 C2 116.59(13) . .
C5 C4 C4 119.19(9) . 2_655
C5 C4 C2 121.38(14) . .
C4 C4 C2 119.39(9) 2_655 .
C6 C5 C4 120.90(15) . .
C6 C6 C5 119.90(10) 2_655 .
C12 C7 C8 120.46(15) . .
C12 C7 N1 119.79(14) . .
C8 C7 N1 119.74(15) . .
C9 C8 C7 119.11(17) . .
C10 C9 C8 120.72(17) . .
C11 C10 C9 119.91(17) . .
C10 C11 C12 120.35(18) . .
C7 C12 C11 119.40(16) . .
C18 C13 C14 118.78(15) . .
C18 C13 C3 121.79(14) . .
C14 C13 C3 119.23(14) . .
C13 C14 C15 120.63(16) . .
C16 C15 C14 119.79(16) . .
C15 C16 C17 120.09(16) . .
C18 C17 C16 119.99(16) . .
C17 C18 C13 120.70(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2107(18) .
N1 C1 1.375(2) .
N1 C7 1.414(2) .
N1 C3 1.4814(19) .
C1 C2 1.519(2) .
C2 C4 1.506(2) .
C2 C3 1.573(2) .
C3 C13 1.499(2) .
C4 C5 1.390(2) .
C4 C4 1.407(3) 2_655
C5 C6 1.384(2) .
C6 C6 1.384(3) 2_655
C7 C12 1.385(2) .
C7 C8 1.394(2) .
C8 C9 1.385(3) .
C9 C10 1.385(3) .
C10 C11 1.374(2) .
C11 C12 1.397(2) .
C13 C18 1.388(2) .
C13 C14 1.388(2) .
C14 C15 1.389(2) .
C15 C16 1.378(3) .
C16 C17 1.382(2) .
C17 C18 1.382(2) .
