#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:11:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178839 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/93/4109359.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_4109359
loop_
_publ_author_name
'Audrey Chan'
'Karl A. Scheidt'
_publ_contact_author_email       scheidt@northwestern.edu
_publ_contact_author_name        'Karl Scheidt'
_publ_section_title
;
 Highly Stereoselective Formal [3 + 3] Cycloaddition of Enals and
 Azomethine Imines Catalyzed by N-Heterocyclic Carbenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5334
_journal_page_last               5335
_journal_paper_doi               10.1021/ja0709167
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C26 H24 N2 O2'
_chemical_formula_weight         396.47
_chemical_name_systematic
; 
 ? 
;
_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                93.6650(10)
_cell_angle_beta                 95.4380(10)
_cell_angle_gamma                91.5370(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4020(7)
_cell_length_b                   10.0753(7)
_cell_length_c                   10.8800(8)
_cell_measurement_temperature    153(2)
_cell_volume                     1023.34(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9410
_diffrn_reflns_theta_full        28.82
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             420
_refine_diff_density_max         1.540
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          5.080
_refine_ls_shift/su_mean         0.051
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0960P)²+0.6340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1805
_reflns_number_gt                4137
_reflns_number_total             4750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0709167si20070208_105336.cif
_cod_data_source_block           Chan_Scheidt2
_cod_database_code               4109359
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
C1 C 0.89261(19) 0.40262(17) 0.40866(15) 0.0261(4) Uani 1 1 d .
C2 C 0.76481(19) 0.48806(18) 0.42032(17) 0.0290(4) Uani 1 1 d .
H2A H 0.7326 0.5243 0.3403 0.035 Uiso 1 1 calc R
H2B H 0.7869 0.5628 0.4835 0.035 Uiso 1 1 calc R
C3 C 0.65163(18) 0.39174(17) 0.46004(15) 0.0256(4) Uani 1 1 d .
H3 H 0.590(2) 0.441(2) 0.517(2) 0.031 Uiso 1 1 calc .
C4 C 0.55712(18) 0.32172(17) 0.35358(15) 0.0251(3) Uani 1 1 d .
C5 C 0.60381(19) 0.29806(18) 0.23619(16) 0.0292(4) Uani 1 1 d .
H5 H 0.6979 0.3257 0.2219 0.035 Uiso 1 1 calc R
C6 C 0.5142(2) 0.2346(2) 0.14022(17) 0.0342(4) Uani 1 1 d .
H6 H 0.5476 0.2176 0.0612 0.041 Uiso 1 1 calc R
C7 C 0.3755(2) 0.1962(2) 0.15991(19) 0.0379(4) Uani 1 1 d .
H7 H 0.3131 0.1554 0.0937 0.046 Uiso 1 1 calc R
C8 C 0.3283(2) 0.2175(2) 0.27644(19) 0.0362(4) Uani 1 1 d .
H8 H 0.2340 0.1902 0.2903 0.043 Uiso 1 1 calc R
C9 C 0.41930(19) 0.27897(19) 0.37289(17) 0.0304(4) Uani 1 1 d .
H9 H 0.3871 0.2919 0.4528 0.036 Uiso 1 1 calc R
C10 C 0.96511(19) 0.19543(17) 0.51457(16) 0.0269(4) Uani 1 1 d .
C11 C 0.92647(19) 0.14191(17) 0.63379(16) 0.0269(4) Uani 1 1 d .
H11A H 1.0063 0.0916 0.6718 0.032 Uiso 1 1 calc R
H11B H 0.8407 0.0818 0.6183 0.032 Uiso 1 1 calc R
C12 C 0.89631(18) 0.26403(17) 0.71980(15) 0.0243(3) Uani 1 1 d .
H12 H 0.977(2) 0.330(2) 0.714(2) 0.029 Uiso 1 1 calc .
C13 C 0.75874(18) 0.33226(17) 0.66682(15) 0.0246(3) Uani 1 1 d .
H13 H 0.775(2) 0.431(2) 0.678(2) 0.029 Uiso 1 1 calc .
C14 C 0.61976(19) 0.29545(19) 0.71858(16) 0.0294(4) Uani 1 1 d .
C15 C 0.5444(2) 0.1783(2) 0.67904(17) 0.0341(4) Uani 1 1 d .
H15 H 0.5826 0.1174 0.6216 0.041 Uiso 1 1 calc R
C16 C 0.4124(2) 0.1481(2) 0.72244(19) 0.0399(5) Uani 1 1 d .
C17 C 0.3596(2) 0.2378(3) 0.8082(2) 0.0470(6) Uani 1 1 d .
H17 H 0.2709 0.2179 0.8392 0.056 Uiso 1 1 calc R
C18 C 0.4327(2) 0.3536(3) 0.8486(2) 0.0448(5) Uani 1 1 d .
H18 H 0.3949 0.4135 0.9072 0.054 Uiso 1 1 calc R
C19 C 0.5632(2) 0.3841(2) 0.80346(18) 0.0382(5) Uani 1 1 d .
H19 H 0.6135 0.4654 0.8307 0.046 Uiso 1 1 calc R
C20 C 0.90166(18) 0.23525(17) 0.85482(15) 0.0258(3) Uani 1 1 d .
C21 C 0.9809(2) 0.3210(2) 0.94208(18) 0.0357(4) Uani 1 1 d .
H21 H 1.0269 0.3979 0.9160 0.043 Uiso 1 1 calc R
C22 C 0.9943(2) 0.2964(2) 1.06702(19) 0.0408(5) Uani 1 1 d .
H22 H 1.0492 0.3562 1.1252 0.049 Uiso 1 1 calc R
C23 C 0.9277(2) 0.1854(2) 1.10637(17) 0.0368(4) Uani 1 1 d .
H23 H 0.9368 0.1677 1.1914 0.044 Uiso 1 1 calc R
C24 C 0.8481(3) 0.1004(2) 1.0208(2) 0.0461(5) Uani 1 1 d .
H24 H 0.8016 0.0240 1.0474 0.055 Uiso 1 1 calc R
C25 C 0.8345(2) 0.1248(2) 0.89591(18) 0.0400(5) Uani 1 1 d .
H25 H 0.7787 0.0651 0.8383 0.048 Uiso 1 1 calc R
C26 C 0.3280(3) 0.0294(3) 0.6728(3) 0.0519(6) Uani 1 1 d .
H26A H 0.2685 0.0499 0.5979 0.078 Uiso 1 1 calc R
H26B H 0.2666 0.0007 0.7348 0.078 Uiso 1 1 calc R
H26C H 0.3922 -0.0421 0.6525 0.078 Uiso 1 1 calc R
N1 N 0.86872(15) 0.29142(14) 0.47540(13) 0.0242(3) Uani 1 1 d .
N2 N 0.73646(15) 0.29301(14) 0.53109(12) 0.0236(3) Uani 1 1 d .
O1 O 0.99650(14) 0.42288(13) 0.35390(11) 0.0317(3) Uani 1 1 d .
O2 O 1.07027(15) 0.17087(15) 0.46236(13) 0.0376(3) Uani 1 1 d .
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
O1 C1 N1 125.47(16)
O1 C1 C2 128.58(16)
N1 C1 C2 105.95(14)
C1 C2 C3 103.46(14)
N2 C3 C4 110.55(13)
N2 C3 C2 104.22(13)
C4 C3 C2 114.26(14)
C9 C4 C5 118.69(16)
C9 C4 C3 119.21(15)
C5 C4 C3 122.10(16)
C6 C5 C4 120.72(17)
C5 C6 C7 119.92(18)
C8 C7 C6 119.97(18)
C7 C8 C9 119.91(18)
C8 C9 C4 120.75(17)
O2 C10 N1 122.27(16)
O2 C10 C11 126.74(16)
N1 C10 C11 110.70(14)
C10 C11 C12 106.41(14)
C20 C12 C11 113.62(14)
C20 C12 C13 115.47(14)
C11 C12 C13 109.98(13)
N2 C13 C14 105.82(13)
N2 C13 C12 107.38(13)
C14 C13 C12 117.16(14)
C15 C14 C19 119.15(18)
C15 C14 C13 121.30(16)
C19 C14 C13 119.48(18)
C14 C15 C16 121.03(19)
C17 C16 C15 118.5(2)
C17 C16 C26 120.7(2)
C15 C16 C26 120.7(2)
C18 C17 C16 121.35(19)
C17 C18 C19 119.9(2)
C14 C19 C18 120.1(2)
C25 C20 C21 117.99(17)
C25 C20 C12 123.09(16)
C21 C20 C12 118.89(16)
C20 C21 C22 121.32(19)
C23 C22 C21 120.00(19)
C24 C23 C22 119.12(18)
C23 C24 C25 121.0(2)
C20 C25 C24 120.58(19)
C1 N1 C10 128.99(15)
C1 N1 N2 113.68(13)
C10 N1 N2 116.01(13)
N1 N2 C13 111.84(12)
N1 N2 C3 103.17(12)
C13 N2 C3 112.51(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.211(2)
C1 N1 1.398(2)
C1 C2 1.507(3)
C2 C3 1.532(2)
C3 N2 1.499(2)
C3 C4 1.515(2)
C4 C9 1.394(2)
C4 C5 1.398(2)
C5 C6 1.388(3)
C6 C7 1.390(3)
C7 C8 1.388(3)
C8 C9 1.391(3)
C10 O2 1.210(2)
C10 N1 1.402(2)
C10 C11 1.508(2)
C11 C12 1.547(2)
C12 C20 1.512(2)
C12 C13 1.560(2)
C13 N2 1.498(2)
C13 C14 1.517(2)
C14 C15 1.383(3)
C14 C19 1.395(3)
C15 C16 1.402(3)
C16 C17 1.392(3)
C16 C26 1.461(3)
C17 C18 1.365(4)
C18 C19 1.398(3)
C20 C25 1.384(3)
C20 C21 1.389(3)
C21 C22 1.392(3)
C22 C23 1.379(3)
C23 C24 1.375(3)
C24 C25 1.391(3)
N1 N2 1.4339(19)
