#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/51/4115151.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_4115151
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         'C6 H9 N O3'
_chemical_formula_sum            'C6 H9 N O3'
_chemical_formula_weight         143.14
_chemical_name_systematic
;
(E)-2-Butenoic acid 4-amino-4-oxo 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                   20.880(5)
_cell_length_b                   3.9280(10)
_cell_length_c                   8.610(2)
_cell_measurement_reflns_used    822
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      3.0
_cell_volume                     706.2(3)
_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      203(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_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  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4732
_diffrn_reflns_theta_full        28.10
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       prism
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0257
_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)+(0.0350P)²+0.0500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                788
_reflns_number_total             870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0257366_s2_1.cif
_cod_data_source_block
(E)-2-Butenoic_acid_4-amino-4-oxo_ethyl_ester_(1)
_cod_database_code               4115151
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
N1 N 0.21328(6) 0.3752(4) 0.43509(17) 0.0359(3) Uani 1 1 d .
H1A H 0.1820 0.4142 0.3670 0.043 Uiso 1 1 d R
H1B H 0.2121 0.4608 0.5405 0.043 Uiso 1 1 d R
C1 C 0.26543(8) 0.2170(4) 0.38567(17) 0.0305(4) Uani 1 1 d .
O1 O 0.27364(6) 0.1241(3) 0.25094(15) 0.0445(3) Uani 1 1 d .
C2 C 0.31377(7) 0.1498(4) 0.50920(19) 0.0295(3) Uani 1 1 d .
H2 H 0.3064 0.2332 0.6099 0.035 Uiso 1 1 calc R
C3 C 0.36667(8) -0.0236(4) 0.4811(2) 0.0314(3) Uani 1 1 d .
H3 H 0.3750 -0.1019 0.3799 0.038 Uiso 1 1 calc R
O4 O 0.40501(6) -0.0270(3) 0.74155(14) 0.0412(3) Uani 1 1 d .
C4 C 0.41295(8) -0.0964(4) 0.60622(19) 0.0303(3) Uani 1 1 d .
O5 O 0.46558(5) -0.2476(3) 0.55209(15) 0.0349(3) Uani 1 1 d .
C6 C 0.51439(8) -0.3290(4) 0.6673(2) 0.0342(4) Uani 1 1 d .
H6A H 0.4986 -0.5037 0.7390 0.041 Uiso 1 1 calc R
H6B H 0.5255 -0.1257 0.7275 0.041 Uiso 1 1 calc R
C7 C 0.57176(8) -0.4573(5) 0.5809(3) 0.0395(4) Uani 1 1 d .
H7A H 0.5848 -0.2899 0.5044 0.047 Uiso 1 1 calc R
H7B H 0.5611 -0.6691 0.5291 0.047 Uiso 1 1 calc R
H7C H 0.6066 -0.4961 0.6534 0.047 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
N1 0.0301(7) 0.0526(9) 0.0249(7) -0.0041(6) -0.0043(6) 0.0044(6)
C1 0.0314(8) 0.0363(8) 0.0237(8) -0.0046(7) 0.0006(7) -0.0046(7)
O1 0.0458(7) 0.0627(8) 0.0250(6) -0.0125(6) -0.0026(6) 0.0045(6)
C2 0.0310(8) 0.0339(8) 0.0236(7) -0.0033(6) 0.0013(6) -0.0037(7)
C3 0.0303(8) 0.0374(8) 0.0264(8) -0.0058(7) 0.0026(6) -0.0022(7)
O4 0.0333(6) 0.0625(8) 0.0277(6) -0.0064(6) 0.0026(5) 0.0061(6)
C4 0.0281(8) 0.0314(7) 0.0313(9) -0.0028(6) 0.0051(6) -0.0026(6)
O5 0.0299(6) 0.0443(6) 0.0306(6) -0.0043(5) 0.0009(5) 0.0064(5)
C6 0.0338(8) 0.0370(8) 0.0319(8) 0.0017(7) 0.0000(7) 0.0026(7)
C7 0.0350(9) 0.0428(9) 0.0408(10) 0.0073(8) 0.0020(8) 0.0073(7)
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 123.89(17)
O1 C1 C2 121.83(16)
N1 C1 C2 114.26(14)
C3 C2 C1 121.84(14)
C2 C3 C4 120.96(15)
O4 C4 O5 123.43(16)
O4 C4 C3 124.79(15)
O5 C4 C3 111.78(14)
C4 O5 C6 115.84(13)
O5 C6 C7 107.15(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.324(2)
C1 O1 1.228(2)
C1 C2 1.490(2)
C2 C3 1.320(2)
C3 C4 1.475(2)
O4 C4 1.208(2)
C4 O5 1.3333(19)
O5 C6 1.458(2)
C6 C7 1.497(2)
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 -2.5(2)
N1 C1 C2 C3 175.86(15)
C1 C2 C3 C4 -178.09(15)
C2 C3 C4 O4 5.0(3)
C2 C3 C4 O5 -174.54(15)
O4 C4 O5 C6 0.3(2)
C3 C4 O5 C6 179.82(13)
C4 O5 C6 C7 -173.48(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4532764
