#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/09/4110935.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_4110935
loop_
_publ_author_name
'Ji Min Lee'
'Doo-Sik Ahn'
'Doo Young Jung'
'Junseung Lee'
'Youngkyu Do'
'Sang Kyu Kim'
'Sukbok Chang'
_publ_section_title
;
 Hydrogen-Bond-Directed Highly Stereoselective Synthesis of Z-Enamides via
 Pd-Catalyzed Oxidative Amidation of Conjugated Olefins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12954
_journal_page_last               12962
_journal_paper_doi               10.1021/ja0639315
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 110.78(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.65(7)
_cell_length_b                   8.84(3)
_cell_length_c                   10.87(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1136(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.924
_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  0.0889
_diffrn_reflns_av_sigmaI/netI    0.1364
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6455
_diffrn_reflns_theta_full        28.13
_diffrn_reflns_theta_max         28.13
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             464
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.2466
_refine_ls_R_factor_gt           0.0929
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0959P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2623
_reflns_number_gt                733
_reflns_number_total             2574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0639315si20060605_013812.cif
_cod_data_source_block           sbc55
_cod_database_code               4110935
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.3095(4) 0.5376(5) 0.7786(5) 0.0591(13) Uani 1 1 d .
C2 C 0.4181(4) 0.5865(6) 0.8044(6) 0.0779(16) Uani 1 1 d .
H2 H 0.4564 0.5599 0.7487 0.093 Uiso 1 1 calc R
C3 C 0.4704(5) 0.6758(7) 0.9137(6) 0.0921(19) Uani 1 1 d .
H3 H 0.5441 0.7095 0.9319 0.110 Uiso 1 1 calc R
C4 C 0.4145(5) 0.7130(7) 0.9926(6) 0.0903(18) Uani 1 1 d .
H4 H 0.4502 0.7735 1.0657 0.108 Uiso 1 1 calc R
C5 C 0.3075(5) 0.6655(6) 0.9699(6) 0.0878(18) Uani 1 1 d .
H5 H 0.2702 0.6930 1.0264 0.105 Uiso 1 1 calc R
C6 C 0.2545(4) 0.5758(6) 0.8614(5) 0.0740(15) Uani 1 1 d .
H6 H 0.1813 0.5414 0.8450 0.089 Uiso 1 1 calc R
C7 C 0.2586(4) 0.4437(5) 0.6569(5) 0.0624(14) Uani 1 1 d .
O1 O 0.3109(3) 0.4191(4) 0.5858(4) 0.0870(12) Uani 1 1 d .
N N 0.1532(3) 0.3917(5) 0.6308(4) 0.0640(12) Uani 1 1 d .
H101 H 0.111(3) 0.401(5) 0.686(4) 0.056(12) Uiso 1 1 d .
C8 C 0.1017(4) 0.3042(6) 0.5189(5) 0.0659(14) Uani 1 1 d .
H8 H 0.1429 0.2859 0.4645 0.079 Uiso 1 1 calc R
C9 C -0.0005(4) 0.2452(6) 0.4837(5) 0.0680(14) Uani 1 1 d .
H9 H -0.0460 0.2625 0.5333 0.082 Uiso 1 1 calc R
C10 C -0.0410(4) 0.1514(6) 0.3643(5) 0.0599(13) Uani 1 1 d .
O2 O 0.0093(3) 0.1311(4) 0.2930(3) 0.0793(12) Uani 1 1 d .
O3 O -0.1421(3) 0.0949(4) 0.3475(3) 0.0715(11) Uani 1 1 d .
C11 C -0.1903(4) -0.0023(6) 0.2331(5) 0.0799(16) Uani 1 1 d .
H11A H -0.1423 -0.0897 0.2394 0.096 Uiso 1 1 calc R
H11B H -0.1975 0.0526 0.1532 0.096 Uiso 1 1 calc R
C12 C -0.3030(4) -0.0505(6) 0.2312(5) 0.0937(19) Uani 1 1 d .
H12A H -0.2957 -0.0941 0.3147 0.141 Uiso 1 1 calc R
H12B H -0.3340 -0.1242 0.1630 0.141 Uiso 1 1 calc R
H12C H -0.3524 0.0357 0.2147 0.141 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.066(3) 0.040(3) 0.076(4) 0.012(3) 0.032(3) 0.001(2)
C2 0.071(4) 0.071(4) 0.094(4) 0.008(3) 0.033(3) 0.004(3)
C3 0.084(4) 0.092(5) 0.104(5) -0.014(4) 0.038(4) -0.027(3)
C4 0.097(4) 0.078(4) 0.102(5) -0.023(3) 0.043(4) -0.021(3)
C5 0.100(4) 0.073(4) 0.098(5) -0.022(4) 0.046(4) -0.012(3)
C6 0.077(3) 0.064(4) 0.088(4) -0.001(3) 0.037(3) -0.007(3)
C7 0.068(3) 0.051(3) 0.080(4) 0.015(3) 0.040(3) 0.010(3)
O1 0.085(2) 0.090(3) 0.097(3) -0.010(2) 0.045(2) -0.010(2)
N 0.070(3) 0.058(3) 0.072(3) 0.000(2) 0.034(3) 0.003(2)
C8 0.071(3) 0.054(3) 0.078(4) 0.009(3) 0.032(3) 0.010(3)
C9 0.077(4) 0.060(4) 0.075(4) 0.000(3) 0.036(3) 0.006(3)
C10 0.057(3) 0.060(4) 0.072(3) 0.009(3) 0.034(3) 0.011(2)
O2 0.082(2) 0.082(3) 0.085(3) -0.003(2) 0.043(2) 0.0022(19)
O3 0.073(2) 0.066(3) 0.079(3) -0.0056(19) 0.0314(19) -0.0020(18)
C11 0.099(4) 0.070(4) 0.070(4) -0.011(3) 0.030(3) -0.005(3)
C12 0.096(4) 0.078(4) 0.103(5) -0.007(3) 0.030(4) -0.014(3)
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
C6 C1 C2 119.8(6)
C6 C1 C7 124.1(5)
C2 C1 C7 116.2(5)
C1 C2 C3 119.7(5)
C4 C3 C2 119.5(6)
C3 C4 C5 122.0(6)
C4 C5 C6 119.0(5)
C1 C6 C5 120.0(6)
O1 C7 N 122.3(6)
O1 C7 C1 120.4(6)
N C7 C1 117.3(5)
C7 N C8 119.7(5)
C9 C8 N 125.4(5)
C8 C9 C10 118.5(5)
O2 C10 O3 124.9(6)
O2 C10 C9 124.5(5)
O3 C10 C9 110.6(4)
C10 O3 C11 115.6(4)
O3 C11 C12 106.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.361(7)
C1 C2 1.370(9)
C1 C7 1.499(8)
C2 C3 1.383(8)
C3 C4 1.332(8)
C4 C5 1.354(9)
C5 C6 1.381(8)
C7 O1 1.202(6)
C7 N 1.342(9)
N C8 1.392(7)
C8 C9 1.319(9)
C9 C10 1.471(8)
C10 O2 1.178(6)
C10 O3 1.323(8)
O3 C11 1.455(7)
C11 C12 1.480(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660418
