#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/05/4120583.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_4120583
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            'C21.5 H21 N4 O4.5'
_chemical_formula_weight         407.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.99(3)
_cell_angle_beta                 74.91(3)
_cell_angle_gamma                77.42(3)
_cell_formula_units_Z            2
_cell_length_a                   7.477(3)
_cell_length_b                   11.703(4)
_cell_length_c                   12.598(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.0
_cell_measurement_theta_min      25.0
_cell_volume                     1010.3(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    0.0148
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3748
_diffrn_reflns_theta_full        68.91
_diffrn_reflns_theta_max         68.91
_diffrn_reflns_theta_min         3.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  0.9108
_exptl_absorpt_correction_T_min  0.8903
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.037(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0747
_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)+(0.0641P)²+0.9419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1840
_reflns_number_gt                2850
_reflns_number_total             3748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja412729s_si_004.cif
_cod_data_source_block           vm2084
_cod_original_cell_volume        1010.3(6)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C21.50 H21 N4 O4.50'
_cod_database_code               4120583
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.2928(4) 0.3258(2) 0.4366(2) 0.0582(7) Uani 1 1 d .
H1 H 0.2989 0.3489 0.4946 0.070 Uiso 1 1 calc R
N2 N 0.5531(4) 0.1891(3) 0.5830(2) 0.0604(7) Uani 1 1 d .
N3 N 0.8425(4) -0.0548(2) 0.3163(2) 0.0636(7) Uani 1 1 d .
N4 N 0.5754(4) 0.0792(2) 0.1728(2) 0.0595(7) Uani 1 1 d .
H4 H 0.6693 0.0285 0.1494 0.071 Uiso 1 1 calc R
O1 O 0.9324(4) -0.1108(3) 0.3873(2) 0.1001(10) Uani 1 1 d .
O2 O 0.8642(4) -0.0832(2) 0.2261(2) 0.0844(8) Uani 1 1 d .
O3 O 0.4456(4) 0.2760(3) 0.6139(2) 0.0849(8) Uani 1 1 d .
O4 O 0.6543(4) 0.1208(2) 0.6425(2) 0.0848(8) Uani 1 1 d .
C1 C 0.1153(4) 0.5122(3) 0.3528(2) 0.0545(7) Uani 1 1 d .
C2 C -0.0370(5) 0.5697(3) 0.3035(3) 0.0664(9) Uani 1 1 d .
H2 H -0.0614 0.6534 0.2848 0.080 Uiso 1 1 calc R
C3 C -0.1525(5) 0.5060(3) 0.2816(3) 0.0702(9) Uani 1 1 d .
H3 H -0.2521 0.5467 0.2476 0.084 Uiso 1 1 calc R
C4 C -0.1213(5) 0.3828(3) 0.3099(3) 0.0667(9) Uani 1 1 d .
H4A H -0.1983 0.3398 0.2941 0.080 Uiso 1 1 calc R
C5 C 0.0251(4) 0.3226(3) 0.3620(3) 0.0601(8) Uani 1 1 d .
H5 H 0.0442 0.2389 0.3838 0.072 Uiso 1 1 calc R
C6 C 0.1431(4) 0.3866(3) 0.3816(2) 0.0522(7) Uani 1 1 d .
C7 C 0.2422(5) 0.5816(3) 0.3735(3) 0.0721(9) Uani 1 1 d .
H7A H 0.2418 0.5620 0.4527 0.108 Uiso 1 1 calc R
H7B H 0.1994 0.6662 0.3493 0.108 Uiso 1 1 calc R
H7C H 0.3672 0.5616 0.3318 0.108 Uiso 1 1 calc R
C9 C 0.4264(4) 0.2352(2) 0.4065(2) 0.0492(7) Uani 1 1 d .
C10 C 0.5559(4) 0.1675(3) 0.4752(2) 0.0487(7) Uani 1 1 d .
C11 C 0.6890(4) 0.0767(3) 0.4413(2) 0.0513(7) Uani 1 1 d .
H11 H 0.7743 0.0352 0.4863 0.062 Uiso 1 1 calc R
C12 C 0.6994(4) 0.0453(2) 0.3416(2) 0.0507(7) Uani 1 1 d .
C13 C 0.5727(4) 0.1079(3) 0.2702(2) 0.0491(7) Uani 1 1 d .
C14 C 0.4423(4) 0.2029(3) 0.3055(2) 0.0499(7) Uani 1 1 d .
H14 H 0.3612 0.2472 0.2587 0.060 Uiso 1 1 calc R
C20 C 0.4389(4) 0.1244(3) 0.1053(2) 0.0531(7) Uani 1 1 d .
C21 C 0.2486(5) 0.1292(3) 0.1536(3) 0.0652(9) Uani 1 1 d .
H21 H 0.2096 0.1036 0.2315 0.078 Uiso 1 1 calc R
C22 C 0.1179(5) 0.1714(3) 0.0876(3) 0.0721(9) Uani 1 1 d .
H22 H -0.0093 0.1754 0.1205 0.087 Uiso 1 1 calc R
C23 C 0.1769(5) 0.2080(3) -0.0288(3) 0.0731(10) Uani 1 1 d .
H23 H 0.0892 0.2379 -0.0742 0.088 Uiso 1 1 calc R
C24 C 0.3650(5) 0.1999(3) -0.0766(3) 0.0681(9) Uani 1 1 d .
H24 H 0.4028 0.2217 -0.1549 0.082 Uiso 1 1 calc R
C25 C 0.5000(5) 0.1604(3) -0.0122(2) 0.0579(8) Uani 1 1 d .
C26 C 0.7048(5) 0.1547(4) -0.0662(3) 0.0804(11) Uani 1 1 d .
H26A H 0.7197 0.1836 -0.1466 0.121 Uiso 1 1 calc R
H26B H 0.7667 0.0729 -0.0492 0.121 Uiso 1 1 calc R
H26C H 0.7591 0.2039 -0.0375 0.121 Uiso 1 1 calc R
C80 C 0.491(2) 0.5078(18) 0.9625(10) 0.144(5) Uani 0.50 1 d PDU
O81 O 0.634(3) 0.480(2) 1.0145(18) 0.271(9) Uani 0.50 1 d PDU
C82 C 0.297(3) 0.4894(17) 1.0454(14) 0.197(9) Uani 0.50 1 d PDU
C83 C 0.4807(19) 0.5409(14) 0.8556(8) 0.147(5) Uani 0.50 1 d PDU
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
C9 N1 C6 126.2(2) . .
O4 N2 O3 121.2(3) . .
O4 N2 C10 119.4(3) . .
O3 N2 C10 119.3(3) . .
O1 N3 O2 122.2(3) . .
O1 N3 C12 118.5(3) . .
O2 N3 C12 119.3(3) . .
C13 N4 C20 126.6(3) . .
C2 C1 C6 116.9(3) . .
C2 C1 C7 121.4(3) . .
C6 C1 C7 121.7(3) . .
C3 C2 C1 121.7(3) . .
C4 C3 C2 120.2(3) . .
C3 C4 C5 119.7(3) . .
C6 C5 C4 119.9(3) . .
C5 C6 C1 121.4(3) . .
C5 C6 N1 120.5(3) . .
C1 C6 N1 118.0(3) . .
N1 C9 C14 120.7(3) . .
N1 C9 C10 122.7(3) . .
C14 C9 C10 116.7(3) . .
C11 C10 C9 120.7(3) . .
C11 C10 N2 116.6(3) . .
C9 C10 N2 122.7(3) . .
C10 C11 C12 121.3(3) . .
C11 C12 C13 120.8(3) . .
C11 C12 N3 116.4(3) . .
C13 C12 N3 122.9(3) . .
N4 C13 C14 120.7(3) . .
N4 C13 C12 122.9(3) . .
C14 C13 C12 116.4(3) . .
C9 C14 C13 124.1(3) . .
C21 C20 C25 120.3(3) . .
C21 C20 N4 121.1(3) . .
C25 C20 N4 118.6(3) . .
C22 C21 C20 120.6(3) . .
C21 C22 C23 119.5(3) . .
C24 C23 C22 119.8(3) . .
C23 C24 C25 122.1(3) . .
C24 C25 C20 117.6(3) . .
C24 C25 C26 121.2(3) . .
C20 C25 C26 121.2(3) . .
O81 C80 C80 92(2) 2_667 2_667
O81 C80 C83 91.9(19) 2_667 .
C80 C80 C83 172(3) 2_667 .
O81 C80 O81 134.6(15) 2_667 .
C80 C80 O81 42.6(17) 2_667 .
C83 C80 O81 133.1(16) . .
O81 C80 C82 160(3) 2_667 2_667
C80 C80 C82 73(2) 2_667 2_667
C83 C80 C82 101.8(12) . 2_667
O81 C80 C82 32.1(11) . 2_667
O81 C80 C82 23.8(17) 2_667 .
C80 C80 C82 72(2) 2_667 .
C83 C80 C82 113.2(13) . .
O81 C80 C82 113.6(11) . .
C82 C80 C82 144.8(10) 2_667 .
C82 O81 C80 130(3) 2_667 2_667
C82 O81 C80 90(2) 2_667 .
C80 O81 C80 45.4(15) 2_667 .
C82 O81 C83 159(3) 2_667 2_667
C80 O81 C83 54.3(16) 2_667 2_667
C80 O81 C83 99.4(14) . 2_667
O81 C82 C80 58.3(18) 2_667 2_667
O81 C82 C80 26.0(19) 2_667 .
C80 C82 C80 35.2(10) 2_667 .
C80 C83 O81 33.8(10) . 2_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.353(4) .
N1 C6 1.423(4) .
N2 O4 1.214(3) .
N2 O3 1.238(3) .
N2 C10 1.442(4) .
N3 O1 1.216(3) .
N3 O2 1.231(4) .
N3 C12 1.449(4) .
N4 C13 1.352(4) .
N4 C20 1.419(4) .
C1 C2 1.393(4) .
C1 C6 1.395(4) .
C1 C7 1.486(5) .
C2 C3 1.377(5) .
C3 C4 1.368(5) .
C4 C5 1.382(4) .
C5 C6 1.381(4) .
C9 C14 1.394(4) .
C9 C10 1.428(4) .
C10 C11 1.368(4) .
C11 C12 1.383(4) .
C12 C13 1.422(4) .
C13 C14 1.400(4) .
C20 C21 1.389(4) .
C20 C25 1.402(4) .
C21 C22 1.370(5) .
C22 C23 1.388(5) .
C23 C24 1.372(5) .
C24 C25 1.381(4) .
C25 C26 1.500(5) .
C80 O81 0.90(3) 2_667
C80 C80 0.95(3) 2_667
C80 C83 1.314(13) .
C80 O81 1.331(14) .
C80 C82 1.56(3) 2_667
C80 C82 1.571(17) .
O81 C82 0.83(3) 2_667
O81 C80 0.90(3) 2_667
O81 C83 1.62(2) 2_667
C82 O81 0.83(3) 2_667
C82 C80 1.56(3) 2_667
C83 O81 1.62(2) 2_667
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
C6 C1 C2 C3 -1.5(5) . .
C7 C1 C2 C3 178.4(3) . .
C1 C2 C3 C4 1.0(5) . .
C2 C3 C4 C5 0.9(5) . .
C3 C4 C5 C6 -2.3(5) . .
C4 C5 C6 C1 1.8(5) . .
C4 C5 C6 N1 179.1(3) . .
C2 C1 C6 C5 0.1(4) . .
C7 C1 C6 C5 -179.8(3) . .
C2 C1 C6 N1 -177.3(3) . .
C7 C1 C6 N1 2.8(4) . .
C9 N1 C6 C5 52.9(4) . .
C9 N1 C6 C1 -129.7(3) . .
C6 N1 C9 C14 8.5(5) . .
C6 N1 C9 C10 -170.8(3) . .
N1 C9 C10 C11 -179.9(3) . .
C14 C9 C10 C11 0.7(4) . .
N1 C9 C10 N2 0.9(4) . .
C14 C9 C10 N2 -178.5(3) . .
O4 N2 C10 C11 -6.6(4) . .
O3 N2 C10 C11 174.4(3) . .
O4 N2 C10 C9 172.6(3) . .
O3 N2 C10 C9 -6.4(4) . .
C9 C10 C11 C12 -1.8(4) . .
N2 C10 C11 C12 177.4(2) . .
C10 C11 C12 C13 0.8(4) . .
C10 C11 C12 N3 -178.1(3) . .
O1 N3 C12 C11 6.1(4) . .
O2 N3 C12 C11 -176.6(3) . .
O1 N3 C12 C13 -172.8(3) . .
O2 N3 C12 C13 4.6(4) . .
C20 N4 C13 C14 -10.1(5) . .
C20 N4 C13 C12 170.1(3) . .
C11 C12 C13 N4 -178.9(3) . .
N3 C12 C13 N4 -0.1(4) . .
C11 C12 C13 C14 1.3(4) . .
N3 C12 C13 C14 -179.9(3) . .
N1 C9 C14 C13 -177.9(3) . .
C10 C9 C14 C13 1.5(4) . .
N4 C13 C14 C9 177.7(3) . .
C12 C13 C14 C9 -2.5(4) . .
C13 N4 C20 C21 -46.7(5) . .
C13 N4 C20 C25 135.4(3) . .
C25 C20 C21 C22 -1.3(5) . .
N4 C20 C21 C22 -179.1(3) . .
C20 C21 C22 C23 0.9(6) . .
C21 C22 C23 C24 1.0(6) . .
C22 C23 C24 C25 -2.5(6) . .
C23 C24 C25 C20 2.1(5) . .
C23 C24 C25 C26 -178.7(4) . .
C21 C20 C25 C24 -0.2(5) . .
N4 C20 C25 C24 177.7(3) . .
C21 C20 C25 C26 -179.4(3) . .
N4 C20 C25 C26 -1.5(5) . .
O81 C80 O81 C82 -156(6) 2_667 2_667
C80 C80 O81 C82 -156(6) 2_667 2_667
C83 C80 O81 C82 15(3) . 2_667
C82 C80 O81 C82 -170(2) . 2_667
O81 C80 O81 C80 0.000(4) 2_667 2_667
C83 C80 O81 C80 171(5) . 2_667
C82 C80 O81 C80 156(6) 2_667 2_667
C82 C80 O81 C80 -14(3) . 2_667
O81 C80 O81 C83 5(3) 2_667 2_667
C80 C80 O81 C83 5(3) 2_667 2_667
C83 C80 O81 C83 176.4(19) . 2_667
C82 C80 O81 C83 161(4) 2_667 2_667
C82 C80 O81 C83 -8.2(16) . 2_667
C80 C80 C82 O81 146(8) 2_667 2_667
C83 C80 C82 O81 -28(5) . 2_667
O81 C80 C82 O81 156(5) . 2_667
C82 C80 C82 O81 146(8) 2_667 2_667
O81 C80 C82 C80 -146(8) 2_667 2_667
C83 C80 C82 C80 -174(4) . 2_667
O81 C80 C82 C80 10(2) . 2_667
C82 C80 C82 C80 0.000(3) 2_667 2_667
C80 C80 C83 O81 -121(24) 2_667 2_667
O81 C80 C83 O81 -174(3) . 2_667
C82 C80 C83 O81 -166(4) 2_667 2_667
C82 C80 C83 O81 11(2) . 2_667
