#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/51/4115152.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_4115152
loop_
_publ_author_name
'Paul W. Baures'
'Alicia M. Beatty'
'Muthu Dhanasekaran'
'Brian A. Helfrich'
'Waleska Pérez-Segarra'
'John Desper'
_publ_section_title
;
 Solution and Solid-State Models of Peptide CH...O Hydrogen Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11315
_journal_page_last               11323
_journal_paper_doi               10.1021/ja0257366
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety
;
C13 H15 N O3
;
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_chemical_name_common
;
N-benzyl fumaric hemiamide ethyl ester
;
_chemical_name_systematic
;
(E)-2-Butenoic acid 4-oxo-4[(phenylmethyl)amino] ethyl ester
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.632(4)
_cell_length_b                   14.097(3)
_cell_length_c                   4.9199(10)
_cell_measurement_reflns_used    1012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      3.1
_cell_volume                     1222.9(5)
_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 0.948
_diffrn_measured_fraction_theta_max 0.948
_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  0.0641
_diffrn_reflns_av_sigmaI/netI    0.0793
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8253
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1598
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0436
_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)+(0.0199P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                799
_reflns_number_total             1598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0257366_s2_2.cif
_cod_data_source_block
(E)-2-Butenoic_acid_4-oxo-4[(phenylmethyl)amino]_ethyl_ester_(2)
_cod_original_cell_volume        1222.8(4)
_cod_database_code               4115152
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'
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 0.4485(2) 0.7203(2) 0.0576(7) 0.0371(9) Uani 1 1 d .
C2 C 0.3764(2) 0.6895(2) -0.0021(8) 0.0505(11) Uani 1 1 d .
H2 H 0.3350 0.7165 0.0860 0.061 Uiso 1 1 calc R
C3 C 0.3650(2) 0.6185(3) -0.1926(9) 0.0608(12) Uani 1 1 d .
H3 H 0.3160 0.5982 -0.2323 0.073 Uiso 1 1 calc R
C4 C 0.4253(2) 0.5783(3) -0.3219(8) 0.0581(12) Uani 1 1 d .
H4 H 0.4176 0.5305 -0.4491 0.070 Uiso 1 1 calc R
C5 C 0.4970(2) 0.6083(3) -0.2642(7) 0.0516(11) Uani 1 1 d .
H5 H 0.5381 0.5814 -0.3543 0.062 Uiso 1 1 calc R
C6 C 0.5091(2) 0.6781(2) -0.0742(7) 0.0423(10) Uani 1 1 d .
H6 H 0.5583 0.6972 -0.0339 0.051 Uiso 1 1 calc R
C7 C 0.4615(2) 0.7991(2) 0.2585(7) 0.0489(11) Uani 1 1 d .
H7A H 0.4343 0.7854 0.4255 0.059 Uiso 1 1 calc R
H7B H 0.5151 0.8033 0.3009 0.059 Uiso 1 1 calc R
O1 O 0.41757(14) 0.95770(16) 0.5582(4) 0.0476(7) Uani 1 1 d .
N1 N 0.43538(15) 0.88944(18) 0.1481(5) 0.0378(8) Uani 1 1 d .
H1 H 0.4363 0.8965 -0.0550 0.045 Uiso 1 1 d R
C8 C 0.41561(18) 0.9619(2) 0.3098(7) 0.0336(9) Uani 1 1 d .
C9 C 0.38898(18) 1.0458(2) 0.1603(6) 0.0349(9) Uani 1 1 d .
H9 H 0.3943 1.0459 -0.0278 0.042 Uiso 1 1 calc R
C10 C 0.35772(18) 1.1215(2) 0.2764(7) 0.0373(9) Uani 1 1 d .
H10 H 0.3542 1.1246 0.4648 0.045 Uiso 1 1 calc R
C11 C 0.3288(2) 1.2000(3) 0.1117(7) 0.0420(10) Uani 1 1 d .
O2 O 0.32803(18) 1.2030(2) -0.1306(5) 0.0955(12) Uani 1 1 d .
O3 O 0.30104(13) 1.26933(15) 0.2635(4) 0.0467(7) Uani 1 1 d .
C12 C 0.2699(2) 1.3505(3) 0.1219(7) 0.0625(13) Uani 1 1 d .
H12A H 0.2200 1.3352 0.0511 0.075 Uiso 1 1 calc R
H12B H 0.3024 1.3675 -0.0296 0.075 Uiso 1 1 calc R
C13 C 0.2644(2) 1.4304(2) 0.3121(9) 0.0735(14) Uani 1 1 d .
H13A H 0.3067 1.4290 0.4347 0.088 Uiso 1 1 calc R
H13B H 0.2180 1.4255 0.4137 0.088 Uiso 1 1 calc R
H13C H 0.2647 1.4889 0.2124 0.088 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
C2 C1 C6 118.5(3)
C2 C1 C7 121.0(3)
C6 C1 C7 120.5(3)
C1 C2 C3 120.5(4)
C4 C3 C2 120.1(4)
C3 C4 C5 119.9(4)
C4 C5 C6 120.5(4)
C5 C6 C1 120.5(4)
N1 C7 C1 110.6(3)
C8 N1 C7 121.7(3)
O1 C8 N1 123.2(3)
O1 C8 C9 123.2(3)
N1 C8 C9 113.5(3)
C10 C9 C8 124.3(3)
C9 C10 C11 120.9(3)
O2 C11 O3 122.2(4)
O2 C11 C10 125.8(4)
O3 C11 C10 112.0(3)
C11 O3 C12 116.9(3)
O3 C12 C13 108.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.375(4)
C1 C6 1.384(4)
C1 C7 1.504(4)
C2 C3 1.386(5)
C3 C4 1.363(5)
C4 C5 1.364(5)
C5 C6 1.374(4)
C7 N1 1.459(4)
O1 C8 1.224(4)
N1 C8 1.341(4)
C8 C9 1.470(4)
C9 C10 1.330(4)
C10 C11 1.462(4)
C11 O2 1.193(4)
C11 O3 1.325(4)
O3 C12 1.449(4)
C12 C13 1.467(5)
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
C6 C1 C2 C3 -0.8(5)
C7 C1 C2 C3 178.4(3)
C1 C2 C3 C4 0.2(6)
C2 C3 C4 C5 -0.2(6)
C3 C4 C5 C6 0.8(6)
C4 C5 C6 C1 -1.3(5)
C2 C1 C6 C5 1.3(5)
C7 C1 C6 C5 -177.9(3)
C2 C1 C7 N1 -69.9(4)
C6 C1 C7 N1 109.2(4)
C1 C7 N1 C8 156.1(3)
C7 N1 C8 O1 -0.4(5)
C7 N1 C8 C9 -178.4(3)
O1 C8 C9 C10 -6.7(6)
N1 C8 C9 C10 171.3(3)
C8 C9 C10 C11 -176.6(3)
C9 C10 C11 O2 2.4(6)
C9 C10 C11 O3 -179.0(3)
O2 C11 O3 C12 -0.6(6)
C10 C11 O3 C12 -179.3(3)
C11 O3 C12 C13 -162.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9991804
