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#$Date: 2016-03-22 11:11:11 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178888 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/17/4111796.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_4111796
loop_
_publ_author_name
'David A. Evans'
'Keith R. Fandrick'
'Hyun-Ji Song'
_publ_section_title
;
 Enantioselective Friedel-Crafts Alkylations of α,β-Unsaturated 2-Acyl
 Imidazoles Catalyzed by Bis(oxazolinyl)pyridine-Scandium(III) Triflate
 Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8942
_journal_page_last               8943
_journal_paper_doi               10.1021/ja052433d
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C16 H20 N2 O'
_chemical_formula_weight         256.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 115.890(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.059(5)
_cell_length_b                   4.8678(11)
_cell_length_c                   16.912(4)
_cell_measurement_temperature    193(2)
_cell_volume                     1485.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4011
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_meas      0
_exptl_crystal_description       rod
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2306
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0593
_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)+(0.0532P)²+0.2460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                1797
_reflns_number_total             2306
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja052433dsi20050414_113315.cif
_cod_data_source_block           jwu91sad
_cod_database_code               4111796
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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 0.78382(16) 0.4559(6) 0.63720(17) 0.0391(8) Uani 1 1 d .
C2 C 0.82107(17) 0.5629(6) 0.58315(18) 0.0408(7) Uani 1 1 d .
H2A H 0.8260 0.7650 0.5897 0.049 Uiso 1 1 calc R
H2B H 0.7897 0.5215 0.5204 0.049 Uiso 1 1 calc R
C3 C 0.89753(18) 0.4361(8) 0.6107(2) 0.0551(9) Uani 1 1 d .
H3 H 0.8913 0.2324 0.6040 0.066 Uiso 1 1 calc R
C4 C 0.94821(18) 0.4961(7) 0.7053(2) 0.0516(9) Uani 1 1 d .
C5 C 0.9981(2) 0.6993(10) 0.7445(3) 0.0781(12) Uani 1 1 d .
H5 H 1.0106 0.8417 0.7150 0.094 Uiso 1 1 calc R
C6 C 1.0285(2) 0.6642(13) 0.8364(3) 0.0901(16) Uani 1 1 d .
H6 H 1.0655 0.7749 0.8796 0.108 Uiso 1 1 calc R
C7 C 0.9959(2) 0.4506(12) 0.8510(3) 0.0872(14) Uani 1 1 d .
H7 H 1.0052 0.3791 0.9071 0.105 Uiso 1 1 calc R
C8 C 0.72676(19) 0.5756(7) 0.7353(2) 0.0531(9) Uani 1 1 d .
H8 H 0.7447 0.3878 0.7590 0.064 Uiso 1 1 calc R
C9 C 0.6436(2) 0.5622(11) 0.6873(3) 0.0899(15) Uani 1 1 d .
H9A H 0.6292 0.4426 0.6358 0.135 Uiso 1 1 calc R
H9B H 0.6238 0.7471 0.6682 0.135 Uiso 1 1 calc R
H9C H 0.6238 0.4882 0.7266 0.135 Uiso 1 1 calc R
C10 C 0.75728(19) 0.7745(6) 0.81248(19) 0.0449(8) Uani 1 1 d .
C11 C 0.8334(2) 0.8145(8) 0.8558(2) 0.0575(9) Uani 1 1 d .
H11 H 0.8650 0.7207 0.8363 0.069 Uiso 1 1 calc R
C12 C 0.8634(2) 0.9894(9) 0.9270(2) 0.0684(11) Uani 1 1 d .
H12 H 0.9156 1.0116 0.9568 0.082 Uiso 1 1 calc R
C13 C 0.8192(3) 1.1306(8) 0.9550(2) 0.0666(11) Uani 1 1 d .
H13 H 0.8403 1.2534 1.0033 0.080 Uiso 1 1 calc R
C14 C 0.7443(3) 1.0945(8) 0.9132(2) 0.0643(10) Uani 1 1 d .
H14 H 0.7132 1.1917 0.9327 0.077 Uiso 1 1 calc R
C15 C 0.71337(19) 0.9163(7) 0.8422(2) 0.0531(9) Uani 1 1 d .
H15 H 0.6612 0.8920 0.8138 0.064 Uiso 1 1 calc R
C16 C 0.9312(3) 0.5349(12) 0.5503(3) 0.0939(15) Uani 1 1 d .
H16A H 0.9799 0.4499 0.5682 0.141 Uiso 1 1 calc R
H16B H 0.9366 0.7351 0.5543 0.141 Uiso 1 1 calc R
H16C H 0.8986 0.4828 0.4895 0.141 Uiso 1 1 calc R
H1N H 0.7664(15) 0.814(7) 0.6696(17) 0.035(8) Uiso 1 1 d .
H2N H 0.922(3) 0.210(14) 0.764(4) 0.15(3) Uiso 1 1 d .
N1 N 0.75832(15) 0.6435(5) 0.67433(17) 0.0430(7) Uani 1 1 d .
N2 N 0.9461(2) 0.3471(9) 0.7714(2) 0.0796(11) Uani 1 1 d .
O1 O 0.77884(13) 0.2093(4) 0.64664(14) 0.0558(7) 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 122.9(3)
O1 C1 C2 120.7(3)
N1 C1 C2 116.4(3)
C1 C2 C3 112.0(2)
C4 C3 C2 111.7(2)
C4 C3 C16 111.1(3)
C2 C3 C16 110.3(3)
N2 C4 C5 105.7(4)
N2 C4 C3 121.8(3)
C5 C4 C3 132.3(4)
C4 C5 C6 108.7(4)
C7 C6 C5 107.1(4)
C6 C7 N2 108.4(4)
N1 C8 C9 110.4(3)
N1 C8 C10 108.9(3)
C9 C8 C10 115.2(3)
C15 C10 C11 118.0(3)
C15 C10 C8 123.4(3)
C11 C10 C8 118.6(3)
C12 C11 C10 120.5(3)
C13 C12 C11 120.9(4)
C12 C13 C14 119.5(4)
C13 C14 C15 120.3(3)
C10 C15 C14 120.9(3)
C1 N1 C8 123.4(3)
C4 N2 C7 110.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.221(3)
C1 N1 1.330(4)
C1 C2 1.504(4)
C2 C3 1.525(4)
C3 C4 1.503(5)
C3 C16 1.528(5)
C4 N2 1.348(5)
C4 C5 1.357(5)
C5 C6 1.410(6)
C6 C7 1.307(7)
C7 N2 1.375(6)
C8 N1 1.464(4)
C8 C9 1.504(5)
C8 C10 1.523(5)
C10 C15 1.375(4)
C10 C11 1.389(5)
C11 C12 1.379(5)
C12 C13 1.360(5)
C13 C14 1.363(5)
C14 C15 1.389(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.86(3) 2.00(3) 2.854(3) 175(3) 1_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 -51.1(4)
N1 C1 C2 C3 127.8(3)
C1 C2 C3 C4 -59.8(4)
C1 C2 C3 C16 176.1(3)
C2 C3 C4 N2 81.7(4)
C16 C3 C4 N2 -154.7(4)
C2 C3 C4 C5 -92.9(4)
C16 C3 C4 C5 30.7(5)
N2 C4 C5 C6 2.1(4)
C3 C4 C5 C6 177.3(3)
C4 C5 C6 C7 -1.5(5)
C5 C6 C7 N2 0.4(5)
N1 C8 C10 C15 130.1(3)
C9 C8 C10 C15 5.4(5)
N1 C8 C10 C11 -50.4(4)
C9 C8 C10 C11 -175.0(3)
C15 C10 C11 C12 0.7(5)
C8 C10 C11 C12 -178.9(3)
C10 C11 C12 C13 -1.4(5)
C11 C12 C13 C14 1.3(6)
C12 C13 C14 C15 -0.4(6)
C11 C10 C15 C14 0.2(5)
C8 C10 C15 C14 179.8(3)
C13 C14 C15 C10 -0.3(5)
O1 C1 N1 C8 4.7(5)
C2 C1 N1 C8 -174.3(3)
C9 C8 N1 C1 -96.4(4)
C10 C8 N1 C1 136.1(3)
C5 C4 N2 C7 -1.9(4)
C3 C4 N2 C7 -177.8(3)
C6 C7 N2 C4 1.0(5)
