#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/51/4115153.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_4115153
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
;
C12 H15 N O3
;
_chemical_formula_sum            'C12 H15 N O3'
_chemical_formula_weight         221.25
_chemical_name_systematic
;
N-(phenylacetyl)glycine 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                   9.9748(18)
_cell_length_b                   12.130(2)
_cell_length_c                   9.5533(16)
_cell_measurement_reflns_used    833
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.7
_cell_volume                     1155.9(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 0.954
_diffrn_measured_fraction_theta_max 0.954
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7932
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1445
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0333
_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)+(0.0360P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                1106
_reflns_number_total             1445
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0257366_s2_3.cif
_cod_data_source_block           Glycine-N-(phenylacetyl)_ethyl_ester_(3).
_cod_database_code               4115153
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
O8 O 0.49696(15) 0.00697(12) 0.00467(14) 0.0394(4) Uani 1 1 d .
O11 O 0.33255(15) 0.22644(13) -0.12897(16) 0.0443(4) Uani 1 1 d .
O12 O 0.17166(14) 0.13904(11) -0.00775(16) 0.0401(4) Uani 1 1 d .
N9 N 0.42642(18) 0.01649(15) -0.21638(16) 0.0343(4) Uani 1 1 d .
H9 H 0.4508 0.0307 -0.3103 0.041 Uiso 1 1 d R
C1 C 0.75836(19) -0.06787(16) -0.08089(19) 0.0310(4) Uani 1 1 d .
C2 C 0.8788(2) -0.02170(17) -0.0374(2) 0.0370(5) Uani 1 1 d .
H2 H 0.9022 0.0498 -0.0663 0.044 Uiso 1 1 calc R
C3 C 0.9646(2) -0.0809(2) 0.0485(2) 0.0435(6) Uani 1 1 d .
H3 H 1.0457 -0.0487 0.0775 0.052 Uiso 1 1 calc R
C4 C 0.9333(2) -0.1854(2) 0.0918(2) 0.0435(6) Uani 1 1 d .
H4 H 0.9918 -0.2247 0.1506 0.052 Uiso 1 1 calc R
C5 C 0.8146(2) -0.23201(18) 0.0478(2) 0.0424(5) Uani 1 1 d .
H5 H 0.7926 -0.3041 0.0759 0.051 Uiso 1 1 calc R
C6 C 0.7274(2) -0.17376(17) -0.0372(2) 0.0374(5) Uani 1 1 d .
H6 H 0.6464 -0.2064 -0.0656 0.045 Uiso 1 1 calc R
C7 C 0.6655(2) -0.00481(17) -0.1762(2) 0.0354(5) Uani 1 1 d .
H7A H 0.6631 -0.0417 -0.2674 0.043 Uiso 1 1 calc R
H7B H 0.7023 0.0693 -0.1907 0.043 Uiso 1 1 calc R
C8 C 0.5233(2) 0.00573(16) -0.1216(2) 0.0309(5) Uani 1 1 d .
C10 C 0.2905(2) 0.03410(18) -0.1708(2) 0.0346(5) Uani 1 1 d .
H10A H 0.2657 -0.0242 -0.1047 0.042 Uiso 1 1 calc R
H10B H 0.2306 0.0286 -0.2518 0.042 Uiso 1 1 calc R
C11 C 0.2704(2) 0.14450(17) -0.1018(2) 0.0328(5) Uani 1 1 d .
C13 C 0.1324(3) 0.2428(2) 0.0568(3) 0.0601(8) Uani 1 1 d .
H13A H 0.0970 0.2931 -0.0145 0.072 Uiso 1 1 calc R
H13B H 0.2104 0.2777 0.1007 0.072 Uiso 1 1 calc R
C14 C 0.0285(2) 0.2203(2) 0.1634(2) 0.0462(6) Uani 1 1 d .
H14A H -0.0485 0.1861 0.1191 0.055 Uiso 1 1 calc R
H14B H 0.0014 0.2890 0.2070 0.055 Uiso 1 1 calc R
H14C H 0.0645 0.1711 0.2340 0.055 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
C11 O12 C13 116.16(17)
C8 N9 C10 119.52(16)
C6 C1 C2 118.46(19)
C6 C1 C7 121.03(18)
C2 C1 C7 120.49(18)
C3 C2 C1 120.1(2)
C4 C3 C2 121.2(2)
C3 C4 C5 118.9(2)
C4 C5 C6 120.6(2)
C5 C6 C1 120.7(2)
C1 C7 C8 114.16(16)
O8 C8 N9 120.6(2)
O8 C8 C7 122.45(19)
N9 C8 C7 116.95(16)
N9 C10 C11 112.93(17)
O11 C11 O12 124.63(19)
O11 C11 C10 124.93(19)
O12 C11 C10 110.43(17)
O12 C13 C14 108.75(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O8 C8 1.234(2)
O11 C11 1.200(2)
O12 C11 1.334(2)
O12 C13 1.455(3)
N9 C8 1.331(3)
N9 C10 1.440(3)
C1 C6 1.385(3)
C1 C2 1.389(3)
C1 C7 1.507(3)
C2 C3 1.386(3)
C3 C4 1.370(3)
C4 C5 1.378(3)
C5 C6 1.384(3)
C7 C8 1.517(3)
C10 C11 1.506(3)
C13 C14 1.478(3)
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 -0.5(3)
C7 C1 C2 C3 -179.00(19)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 0.4(3)
C3 C4 C5 C6 -0.9(3)
C4 C5 C6 C1 0.6(3)
C2 C1 C6 C5 0.0(3)
C7 C1 C6 C5 178.57(19)
C6 C1 C7 C8 55.3(2)
C2 C1 C7 C8 -126.2(2)
C10 N9 C8 O8 2.5(3)
C10 N9 C8 C7 -175.94(18)
C1 C7 C8 O8 29.1(3)
C1 C7 C8 N9 -152.51(18)
C8 N9 C10 C11 67.5(2)
C13 O12 C11 O11 4.8(3)
C13 O12 C11 C10 -174.0(2)
N9 C10 C11 O11 30.2(3)
N9 C10 C11 O12 -150.99(16)
C11 O12 C13 C14 -176.61(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 208795
