#------------------------------------------------------------------------------
#$Date: 2017-06-04 17:47:33 +0300 (Sun, 04 Jun 2017) $
#$Revision: 197335 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/25/4032539.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_4032539
loop_
_publ_author_name
'Awada, Hawraà'
'Grison, Claire M.'
'Charnay-Pouget, Florence'
'Baltaze, Jean-Pierre'
'Brisset, François'
'Guillot, Régis'
'Robin, Sylvie'
'Hachem, Ali'
'Jaber, Nada'
'Naoufal, Daoud'
'Yazbeck, Ogaritte'
'Aitken, David J.'
_publ_section_title
;
 Conformational Effects through Hydrogen Bonding in a Constrained
 γ-Peptide Template: From Intraresidue Seven-Membered Rings to a
 Gel-Forming Sheet Structure.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4819
_journal_page_last               4828
_journal_paper_doi               10.1021/acs.joc.7b00494
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H25 N O4'
_chemical_formula_sum            'C18 H25 N O4'
_chemical_formula_weight         319.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.5120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.3002(2)
_cell_length_b                   15.1222(7)
_cell_length_c                   10.5712(5)
_cell_measurement_reflns_used    5210
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.35
_cell_volume                     845.70(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10859
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         1.930
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0314P)²+0.1644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0695
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3209
_reflns_number_total             3414
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b00494_si_003.cif
_cod_data_source_block           1b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4032539
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.1600(4) 0.70863(15) 0.2898(2) 0.0230(5) Uani 1 1 d . .
H1 H 0.0321 0.6821 0.3329 0.028 Uiso 1 1 calc R U
C2 C 0.1547(4) 0.70394(15) 0.1590(2) 0.0255(5) Uani 1 1 d . .
H2 H 0.0240 0.6739 0.1148 0.031 Uiso 1 1 calc R U
C3 C 0.3437(4) 0.74392(15) 0.0931(2) 0.0247(5) Uani 1 1 d . .
H3 H 0.3390 0.7415 0.0050 0.030 Uiso 1 1 calc R U
C4 C 0.5379(4) 0.78708(15) 0.1605(2) 0.0240(5) Uani 1 1 d . .
H4 H 0.6660 0.8134 0.1173 0.029 Uiso 1 1 calc R U
C5 C 0.5447(4) 0.79180(14) 0.2918(2) 0.0210(4) Uani 1 1 d . .
H5 H 0.6767 0.8213 0.3359 0.025 Uiso 1 1 calc R U
C6 C 0.3551(4) 0.75269(14) 0.35756(19) 0.0179(4) Uani 1 1 d . .
C7 C 0.3492(4) 0.75692(14) 0.49976(19) 0.0212(4) Uani 1 1 d . .
H7A H 0.1930 0.7843 0.5228 0.025 Uiso 1 1 calc R U
H7B H 0.3567 0.6976 0.5348 0.025 Uiso 1 1 calc R U
C8 C 0.5711(4) 0.82178(13) 0.67673(19) 0.0174(4) Uani 1 1 d . .
C9 C 0.7906(4) 0.87950(14) 0.71838(19) 0.0176(4) Uani 1 1 d . .
H9 H 0.9319 0.8760 0.6630 0.021 Uiso 1 1 calc R U
C10 C 0.8716(4) 0.87011(15) 0.8614(2) 0.0229(5) Uani 1 1 d . .
H10A H 0.8123 0.8161 0.8994 0.027 Uiso 1 1 calc R U
H10B H 1.0514 0.8782 0.8807 0.027 Uiso 1 1 calc R U
C11 C 0.7116(4) 0.95238(14) 0.88969(19) 0.0203(5) Uani 1 1 d . .
H11A H 0.5462 0.9385 0.9189 0.024 Uiso 1 1 calc R U
H11B H 0.7991 0.9951 0.9451 0.024 Uiso 1 1 calc R U
C12 C 0.7084(4) 0.97663(14) 0.74783(18) 0.0157(4) Uani 1 1 d . .
H12 H 0.8486 1.0170 0.7338 0.019 Uiso 1 1 calc R U
C13 C 0.4668(3) 1.01436(13) 0.68712(17) 0.0160(4) Uani 1 1 d . .
H13A H 0.3278 0.9745 0.7007 0.019 Uiso 1 1 calc R U
H13B H 0.4307 1.0706 0.7263 0.019 Uiso 1 1 calc R U
C14 C 0.2839(3) 1.03588(15) 0.47192(17) 0.0161(4) Uani 1 1 d . .
C15 C 0.1635(3) 1.04844(15) 0.24496(17) 0.0174(4) Uani 1 1 d . .
C16 C 0.0152(4) 0.96290(14) 0.2399(2) 0.0245(5) Uani 1 1 d . .
H16A H 0.1302 0.9138 0.2436 0.037 Uiso 1 1 calc R U
H16B H -0.0887 0.9604 0.1624 0.037 Uiso 1 1 calc R U
H16C H -0.0899 0.9602 0.3106 0.037 Uiso 1 1 calc R U
C17 C 0.3275(4) 1.0568(2) 0.1326(2) 0.0325(6) Uani 1 1 d . .
H17A H 0.4197 1.1114 0.1386 0.049 Uiso 1 1 calc R U
H17B H 0.2223 1.0560 0.0554 0.049 Uiso 1 1 calc R U
H17C H 0.4441 1.0082 0.1329 0.049 Uiso 1 1 calc R U
C18 C -0.0055(4) 1.12883(15) 0.2533(2) 0.0238(5) Uani 1 1 d . .
H18A H -0.1172 1.1207 0.3205 0.036 Uiso 1 1 calc R U
H18B H -0.1031 1.1363 0.1745 0.036 Uiso 1 1 calc R U
H18C H 0.0967 1.1804 0.2701 0.036 Uiso 1 1 calc R U
N1 N 0.4888(3) 1.02698(12) 0.55195(15) 0.0165(3) Uani 1 1 d . .
H1A H 0.6365 1.0288 0.5226 0.020 Uiso 1 1 calc R U
O1 O 0.5624(3) 0.80797(10) 0.55069(13) 0.0197(3) Uani 1 1 d . .
O2 O 0.4157(3) 0.79324(11) 0.74452(14) 0.0260(4) Uani 1 1 d . .
O3 O 0.0668(2) 1.03483(12) 0.50471(12) 0.0232(3) Uani 1 1 d . .
O4 O 0.3540(2) 1.04670(11) 0.35266(12) 0.0189(3) 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 0.0033 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 120.5(2)
C1 C2 C3 120.5(2)
C4 C3 C2 118.9(2)
C3 C4 C5 120.9(2)
C6 C5 C4 120.2(2)
C5 C6 C1 118.98(19)
C5 C6 C7 122.76(18)
C1 C6 C7 118.26(18)
O1 C7 C6 109.32(16)
O2 C8 O1 123.36(19)
O2 C8 C9 125.50(19)
O1 C8 C9 111.09(16)
C8 C9 C10 113.34(17)
C8 C9 C12 112.56(16)
C10 C9 C12 87.48(15)
C11 C10 C9 89.57(15)
C12 C11 C10 88.67(15)
C13 C12 C11 117.49(15)
C13 C12 C9 120.56(17)
C11 C12 C9 89.07(15)
N1 C13 C12 110.53(15)
O3 C14 N1 124.03(17)
O3 C14 O4 125.88(17)
N1 C14 O4 110.09(14)
O4 C15 C16 109.96(17)
O4 C15 C18 110.41(17)
C16 C15 C18 112.36(16)
O4 C15 C17 101.96(14)
C16 C15 C17 111.36(19)
C18 C15 C17 110.32(19)
C14 N1 C13 121.50(15)
C8 O1 C7 115.48(15)
C14 O4 C15 120.65(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.383(3)
C1 C6 1.391(3)
C2 C3 1.393(3)
C3 C4 1.380(3)
C4 C5 1.389(3)
C5 C6 1.388(3)
C6 C7 1.507(3)
C7 O1 1.445(2)
C8 O2 1.204(2)
C8 O1 1.347(2)
C8 C9 1.499(3)
C9 C10 1.553(3)
C9 C12 1.569(3)
C10 C11 1.545(3)
C11 C12 1.543(3)
C12 C13 1.509(3)
C13 N1 1.453(2)
C14 O3 1.222(2)
C14 N1 1.342(2)
C14 O4 1.346(2)
C15 O4 1.475(2)
C15 C16 1.513(3)
C15 C18 1.516(3)
C15 C17 1.519(3)
