#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/23/1512343.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_1512343
loop_
_publ_author_name
'Gou, Quan'
'Deng, Bin'
'Zhang, Hongbin'
'Qin, Jun'
_publ_section_title
;
 Arylations of Substituted Enamides by Aryl Iodides: Regio- and
 Stereoselective Synthesis of (Z)-β-Amido-β-Arylacrylates.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4604
_journal_page_last               4607
_journal_paper_doi               10.1021/ol402215f
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.4610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5053(11)
_cell_length_b                   14.4803(18)
_cell_length_c                   9.8588(12)
_cell_measurement_temperature    298(2)
_cell_volume                     1287.1(3)
_computing_cell_refinement       'Bruker apex II'
_computing_data_collection       'Bruker apex II'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7207
_diffrn_reflns_theta_full        25.15
_diffrn_reflns_theta_max         25.15
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0453
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                1668
_reflns_number_total             2305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402215f_si_002.cif
_cod_data_source_block           (E)-3aa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1512343
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.59880(16) 0.10625(9) 0.71562(15) 0.0420(4) Uani 1 1 d .
O1 O 0.4673(2) 0.10453(12) 0.87758(16) 0.0806(6) Uani 1 1 d .
O2 O 0.20690(16) 0.19376(11) 0.36924(15) 0.0722(5) Uani 1 1 d .
O3 O 0.09493(16) 0.08898(10) 0.46300(16) 0.0666(5) Uani 1 1 d .
C1 C 0.5829(3) 0.09689(13) 0.8508(2) 0.0545(6) Uani 1 1 d .
C2 C 0.7335(3) 0.07697(16) 0.9549(2) 0.0688(7) Uani 1 1 d .
H2A H 0.7280 0.0289 1.0216 0.083 Uiso 1 1 calc R
H2B H 0.7762 0.1320 1.0082 0.083 Uiso 1 1 calc R
C3 C 0.8238(2) 0.04539(15) 0.8615(2) 0.0668(7) Uani 1 1 d .
H3A H 0.8154 -0.0208 0.8459 0.080 Uiso 1 1 calc R
H3B H 0.9276 0.0614 0.9040 0.080 Uiso 1 1 calc R
C4 C 0.7549(2) 0.09765(13) 0.7227(2) 0.0535(5) Uani 1 1 d .
H4A H 0.8005 0.1578 0.7256 0.064 Uiso 1 1 calc R
H4B H 0.7644 0.0633 0.6416 0.064 Uiso 1 1 calc R
C5 C 0.48500(19) 0.12890(11) 0.58996(17) 0.0376(4) Uani 1 1 d .
C6 C 0.53311(18) 0.17563(11) 0.47811(17) 0.0391(4) Uani 1 1 d .
C7 C 0.5017(2) 0.13643(14) 0.34382(19) 0.0503(5) Uani 1 1 d .
H7 H 0.4496 0.0811 0.3237 0.060 Uiso 1 1 calc R
C8 C 0.5471(3) 0.17888(18) 0.2395(2) 0.0716(7) Uani 1 1 d .
H8 H 0.5250 0.1526 0.1490 0.086 Uiso 1 1 calc R
C9 C 0.6253(3) 0.2602(2) 0.2702(3) 0.0798(8) Uani 1 1 d .
H9 H 0.6561 0.2890 0.2001 0.096 Uiso 1 1 calc R
C10 C 0.6581(3) 0.29885(16) 0.4029(3) 0.0722(7) Uani 1 1 d .
H10 H 0.7115 0.3537 0.4228 0.087 Uiso 1 1 calc R
C11 C 0.6126(2) 0.25714(12) 0.5077(2) 0.0508(5) Uani 1 1 d .
H11 H 0.6353 0.2838 0.5979 0.061 Uiso 1 1 calc R
C12 C 0.3441(2) 0.10568(12) 0.57414(19) 0.0437(5) Uani 1 1 d .
H12 H 0.3277 0.0675 0.6435 0.052 Uiso 1 1 calc R
C13 C 0.2143(2) 0.13524(13) 0.45750(19) 0.0451(5) Uani 1 1 d .
C14 C -0.0457(3) 0.1156(2) 0.3630(3) 0.0941(9) Uani 1 1 d .
H14A H -0.0603 0.1807 0.3711 0.141 Uiso 1 1 calc R
H14B H -0.1239 0.0823 0.3837 0.141 Uiso 1 1 calc R
H14C H -0.0468 0.1015 0.2676 0.141 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
C1 N1 C5 125.50(16)
C1 N1 C4 111.08(15)
C5 N1 C4 123.20(15)
C13 O3 C14 117.08(16)
O1 C1 N1 125.35(19)
O1 C1 C2 127.0(2)
N1 C1 C2 107.7(2)
C1 C2 C3 104.10(17)
C1 C2 H2A 110.9
C3 C2 H2A 110.9
C1 C2 H2B 110.9
C3 C2 H2B 110.9
H2A C2 H2B 109.0
C2 C3 C4 103.36(16)
C2 C3 H3A 111.1
C4 C3 H3A 111.1
C2 C3 H3B 111.1
C4 C3 H3B 111.1
H3A C3 H3B 109.1
N1 C4 C3 103.10(16)
N1 C4 H4A 111.1
C3 C4 H4A 111.1
N1 C4 H4B 111.1
C3 C4 H4B 111.1
H4A C4 H4B 109.1
C12 C5 N1 120.46(15)
C12 C5 C6 124.00(15)
N1 C5 C6 115.49(15)
C11 C6 C7 119.36(16)
C11 C6 C5 120.61(15)
C7 C6 C5 120.01(16)
C8 C7 C6 120.5(2)
C8 C7 H7 119.8
C6 C7 H7 119.8
C9 C8 C7 119.5(2)
C9 C8 H8 120.2
C7 C8 H8 120.2
C10 C9 C8 120.4(2)
C10 C9 H9 119.8
C8 C9 H9 119.8
C9 C10 C11 120.5(2)
C9 C10 H10 119.7
C11 C10 H10 119.7
C10 C11 C6 119.76(19)
C10 C11 H11 120.1
C6 C11 H11 120.1
C5 C12 C13 125.61(16)
C5 C12 H12 117.2
C13 C12 H12 117.2
O2 C13 O3 121.94(17)
O2 C13 C12 128.22(18)
O3 C13 C12 109.80(15)
O3 C14 H14A 109.5
O3 C14 H14B 109.5
H14A C14 H14B 109.5
O3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.395(3)
N1 C5 1.401(2)
N1 C4 1.468(2)
O1 C1 1.213(3)
O2 C13 1.201(2)
O3 C13 1.333(2)
O3 C14 1.440(3)
C1 C2 1.501(3)
C2 C3 1.515(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.518(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 H4A 0.9700
C4 H4B 0.9700
C5 C12 1.341(3)
C5 C6 1.484(2)
C6 C11 1.382(2)
C6 C7 1.383(2)
C7 C8 1.380(3)
C7 H7 0.9300
C8 C9 1.374(3)
C8 H8 0.9300
C9 C10 1.366(4)
C9 H9 0.9300
C10 C11 1.379(3)
C10 H10 0.9300
C11 H11 0.9300
C12 C13 1.459(2)
C12 H12 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
C5 N1 C1 O1 2.2(3)
C4 N1 C1 O1 176.9(2)
C5 N1 C1 C2 -177.21(15)
C4 N1 C1 C2 -2.5(2)
O1 C1 C2 C3 162.7(2)
N1 C1 C2 C3 -17.9(2)
C1 C2 C3 C4 30.4(2)
C1 N1 C4 C3 21.7(2)
C5 N1 C4 C3 -163.41(15)
C2 C3 C4 N1 -31.5(2)
C1 N1 C5 C12 -29.0(2)
C4 N1 C5 C12 156.90(16)
C1 N1 C5 C6 153.32(16)
C4 N1 C5 C6 -20.8(2)
C12 C5 C6 C11 125.38(18)
N1 C5 C6 C11 -57.0(2)
C12 C5 C6 C7 -56.2(2)
N1 C5 C6 C7 121.39(17)
C11 C6 C7 C8 -1.0(3)
C5 C6 C7 C8 -179.39(17)
C6 C7 C8 C9 0.6(3)
C7 C8 C9 C10 0.0(4)
C8 C9 C10 C11 -0.3(4)
C9 C10 C11 C6 -0.1(3)
C7 C6 C11 C10 0.7(3)
C5 C6 C11 C10 179.10(17)
N1 C5 C12 C13 171.72(15)
C6 C5 C12 C13 -10.8(3)
C14 O3 C13 O2 -3.3(3)
C14 O3 C13 C12 174.6(2)
C5 C12 C13 O2 -11.4(3)
C5 C12 C13 O3 170.85(16)
