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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/05/4120581.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_4120581
loop_
_publ_author_name
'Sebaoun, Laure'
'Maurizot, Victor'
'Granier, Thierry'
'Kauffmann, Brice'
'Huc, Ivan'
_publ_section_title
;
 Aromatic Oligoamide β-Sheet Foldamers.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2168
_journal_page_last               2174
_journal_paper_doi               10.1021/ja412729s
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C12 H8.5 N3.5 O5'
_chemical_formula_weight         281.72
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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            8
_cell_length_a                   15.9840(10)
_cell_length_b                   16.622(7)
_cell_length_c                   9.1600(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.0
_cell_measurement_theta_min      25.0
_cell_volume                     2433.7(11)
_computing_structure_refinement
'SHELXL (Sheldrick, G.M. (2008) Acta Cryst. A64, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, G.M. (2008) Acta Cryst. A64, 112-122)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Enraf Nonius cad-4 diffractometer'
_diffrn_measurement_method       Ω-2\Scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2232
_diffrn_reflns_theta_full        69.84
_diffrn_reflns_theta_max         69.84
_diffrn_reflns_theta_min         5.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.055
_exptl_absorpt_correction_T_max  0.8167
_exptl_absorpt_correction_T_min  0.7784
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0167(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0870P)²+0.7371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1518
_reflns_number_gt                1806
_reflns_number_total             2232
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja412729s_si_003.cif
_cod_data_source_block           vm068b
_cod_original_sg_symbol_H-M      Pnma
_cod_original_formula_sum        'C12 H8.50 N3.50 O5'
_cod_database_code               4120581
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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 0.75311(16) 0.7500 0.2456(3) 0.0658(9) Uani 1 2 d S
H1 H 0.7105 0.7500 0.3147 0.079 Uiso 1 2 calc SR
C2 C 0.78357(11) 0.67771(15) 0.1962(2) 0.0615(6) Uani 1 1 d .
C3 C 0.84823(10) 0.67609(13) 0.0883(2) 0.0553(5) Uani 1 1 d .
C4 C 0.87632(15) 0.7500 0.0379(3) 0.0551(7) Uani 1 2 d S
H4 H 0.9169 0.7500 -0.0349 0.066 Uiso 1 2 calc SR
N5 N 0.74781(11) 0.60584(16) 0.2584(2) 0.0744(6) Uani 1 1 d .
O6 O 0.69968(11) 0.61284(14) 0.3621(2) 0.1005(7) Uani 1 1 d .
O7 O 0.76693(11) 0.53959(13) 0.2067(2) 0.0895(6) Uani 1 1 d .
N8 N 0.87919(10) 0.60566(12) 0.0348(2) 0.0649(5) Uani 1 1 d .
H8 H 0.8549 0.5623 0.0635 0.078 Uiso 1 1 calc R
C9 C 0.94657(11) 0.59641(12) -0.0624(2) 0.0523(5) Uani 1 1 d .
C10 C 0.93962(12) 0.53995(12) -0.1722(2) 0.0603(5) Uani 1 1 d .
H10 H 0.8919 0.5081 -0.1783 0.072 Uiso 1 1 calc R
C11 C 1.00264(13) 0.53056(13) -0.2722(2) 0.0632(6) Uani 1 1 d .
H11 H 0.9983 0.4920 -0.3454 0.076 Uiso 1 1 calc R
C12 C 1.07270(12) 0.57893(12) -0.2633(2) 0.0545(5) Uani 1 1 d .
C13 C 1.08315(11) 0.63152(12) -0.1490(2) 0.0566(5) Uani 1 1 d .
H13 H 1.1321 0.6615 -0.1407 0.068 Uiso 1 1 calc R
C14 C 1.02067(11) 0.63944(13) -0.0473(2) 0.0581(5) Uani 1 1 d .
H14 H 1.0279 0.6737 0.0319 0.070 Uiso 1 1 calc R
N15 N 1.13574(12) 0.57444(13) -0.3778(2) 0.0720(6) Uani 1 1 d .
O16 O 1.12873(12) 0.52201(15) -0.4709(2) 0.1083(8) Uani 1 1 d .
O17 O 1.19363(12) 0.62222(13) -0.3751(2) 0.0959(7) Uani 1 1 d .
C20 C 0.9383(2) 0.7500 0.4710(3) 0.0695(9) Uani 1 2 d S
C21 C 0.90492(16) 0.67815(16) 0.5167(3) 0.0777(7) Uani 1 1 d .
H21 H 0.9268 0.6296 0.4835 0.093 Uiso 1 1 calc R
C22 C 0.83891(16) 0.67914(16) 0.6118(3) 0.0778(7) Uani 1 1 d .
H22 H 0.8162 0.6309 0.6445 0.093 Uiso 1 1 calc R
C23 C 0.8064(2) 0.7500 0.6590(4) 0.0737(9) Uani 1 2 d S
H23 H 0.7616 0.7500 0.7239 0.088 Uiso 1 2 calc SR
N24 N 1.0093(2) 0.7500 0.3713(4) 0.1097(13) Uani 1 2 d S
O25 O 1.0371(2) 0.6869(2) 0.3300(4) 0.1728(15) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C2 122.1(3) 8_575 .
C1 C2 C3 120.0(2) . .
C1 C2 N5 117.01(19) . .
C3 C2 N5 123.0(2) . .
N8 C3 C4 121.58(18) . .
N8 C3 C2 121.84(19) . .
C4 C3 C2 116.6(2) . .
C3 C4 C3 124.7(2) . 8_575
O6 N5 O7 122.4(2) . .
O6 N5 C2 118.4(2) . .
O7 N5 C2 119.20(19) . .
C3 N8 C9 126.89(17) . .
C10 C9 C14 119.39(18) . .
C10 C9 N8 118.31(17) . .
C14 C9 N8 122.24(18) . .
C11 C10 C9 120.36(18) . .
C10 C11 C12 119.36(19) . .
C13 C12 C11 120.91(19) . .
C13 C12 N15 119.80(17) . .
C11 C12 N15 119.28(18) . .
C14 C13 C12 119.33(18) . .
C13 C14 C9 120.21(18) . .
O17 N15 O16 123.1(2) . .
O17 N15 C12 118.51(18) . .
O16 N15 C12 118.34(19) . .
C21 C20 C21 120.8(3) 8_575 .
C21 C20 N24 119.61(17) 8_575 .
C21 C20 N24 119.61(17) . .
C22 C21 C20 118.9(3) . .
C23 C22 C21 120.6(3) . .
C22 C23 C22 120.3(4) 8_575 .
O25 N24 O25 121.9(5) 8_575 .
O25 N24 C20 119.0(2) 8_575 .
O25 N24 C20 119.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.373(3) 8_575
C1 C2 1.373(3) .
C2 C3 1.430(3) .
C2 N5 1.442(3) .
C3 N8 1.362(3) .
C3 C4 1.387(2) .
C4 C3 1.387(2) 8_575
N5 O6 1.228(2) .
N5 O7 1.237(3) .
N8 C9 1.406(2) .
C9 C10 1.380(3) .
C9 C14 1.391(3) .
C10 C11 1.371(3) .
C11 C12 1.381(3) .
C12 C13 1.374(3) .
C12 N15 1.456(3) .
C13 C14 1.372(3) .
N15 O17 1.220(2) .
N15 O16 1.225(2) .
C20 C21 1.374(3) 8_575
C20 C21 1.374(3) .
C20 N24 1.457(5) .
C21 C22 1.369(4) .
C22 C23 1.358(3) .
C23 C22 1.358(3) 8_575
N24 O25 1.200(3) 8_575
N24 O25 1.200(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 -0.9(4) 8_575 .
C2 C1 C2 N5 178.73(17) 8_575 .
C1 C2 C3 N8 -178.9(2) . .
N5 C2 C3 N8 1.4(3) . .
C1 C2 C3 C4 -0.6(3) . .
N5 C2 C3 C4 179.72(19) . .
N8 C3 C4 C3 -179.36(16) . 8_575
C2 C3 C4 C3 2.3(4) . 8_575
C1 C2 N5 O6 -8.0(3) . .
C3 C2 N5 O6 171.69(19) . .
C1 C2 N5 O7 172.5(2) . .
C3 C2 N5 O7 -7.8(3) . .
C4 C3 N8 C9 7.0(3) . .
C2 C3 N8 C9 -174.80(17) . .
C3 N8 C9 C10 -139.2(2) . .
C3 N8 C9 C14 43.8(3) . .
C14 C9 C10 C11 -4.9(3) . .
N8 C9 C10 C11 177.97(19) . .
C9 C10 C11 C12 -0.9(3) . .
C10 C11 C12 C13 5.4(3) . .
C10 C11 C12 N15 -174.0(2) . .
C11 C12 C13 C14 -4.0(3) . .
N15 C12 C13 C14 175.4(2) . .
C12 C13 C14 C9 -1.9(3) . .
C10 C9 C14 C13 6.3(3) . .
N8 C9 C14 C13 -176.66(19) . .
C13 C12 N15 O17 -5.5(3) . .
C11 C12 N15 O17 173.9(2) . .
C13 C12 N15 O16 173.4(2) . .
C11 C12 N15 O16 -7.2(3) . .
C21 C20 C21 C22 -1.7(5) 8_575 .
N24 C20 C21 C22 179.2(3) . .
C20 C21 C22 C23 0.7(4) . .
C21 C22 C23 C22 0.2(5) . 8_575
C21 C20 N24 O25 -0.5(5) 8_575 8_575
C21 C20 N24 O25 178.7(4) . 8_575
C21 C20 N24 O25 -178.7(4) 8_575 .
C21 C20 N24 O25 0.5(5) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122491
