#------------------------------------------------------------------------------
#$Date: 2019-11-11 20:31:11 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227280 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035868.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_4035868
loop_
_publ_author_name
'Dumonteil, Geoffrey'
'Bhattacharjee, Nicholus'
'Angelici, Gaetano'
'Roy, Olivier'
'Faure, Sophie'
'Jouffret, Laurent'
'Jolibois, Franck'
'Perrin, Lionel'
'Taillefumier, Claude'
_publ_section_title
;
 Exploring the Conformation of Mixed Cis- Trans α,β-Oligopeptoids:
 A Joint Experimental and Computational Study.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6382
_journal_page_last               6396
_journal_paper_doi               10.1021/acs.joc.8b00606
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C19 H28 N2 O4'
_chemical_formula_weight         348.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.830(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.322(12)
_cell_length_b                   5.730(4)
_cell_length_c                   19.274(13)
_cell_measurement_reflns_used    706
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.70
_cell_measurement_theta_min      6.641
_cell_volume                     1915(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1359
_diffrn_reflns_av_unetI/netI     0.1864
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6655
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.210
_diffrn_reflns_theta_max         25.210
_diffrn_reflns_theta_min         3.727
_diffrn_source                   molybdene
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7270
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       platelet
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.914
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.068(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1810
_refine_ls_R_factor_gt           0.0978
_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)+(0.1311P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2205
_refine_ls_wR_factor_ref         0.2674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1233
_reflns_number_total             2355
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00606_si_002.cif
_cod_data_source_block           2018_GD155
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035868
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.7272(3) 0.8458(8) 0.9307(3) 0.0522(17) Uani 1 1 d . .
O2 O 0.6748(3) 0.5706(8) 0.8470(3) 0.0513(17) Uani 1 1 d . .
O3 O 0.4652(2) 0.6841(7) 0.6898(3) 0.0385(14) Uani 1 1 d . .
O4 O 0.5045(3) 0.2164(7) 0.9167(3) 0.0395(14) Uani 1 1 d . .
N1 N 0.5679(3) 0.8932(8) 0.7617(3) 0.0321(16) Uani 1 1 d . .
N2 N 0.3993(3) 0.4301(8) 0.8609(4) 0.0333(16) Uani 1 1 d . .
C1 C 0.8615(4) 0.8241(18) 1.0002(6) 0.079(3) Uani 1 1 d . .
H1 H 0.8783 0.8651 0.9584 0.119 Uiso 1 1 calc R U
H3 H 0.9013 0.7295 1.0350 0.119 Uiso 1 1 calc R U
H28 H 0.8530 0.9669 1.0245 0.119 Uiso 1 1 calc R U
C2 C 0.7880(4) 0.6877(15) 0.9738(6) 0.064(3) Uani 1 1 d . .
H26 H 0.7939 0.5550 0.9432 0.077 Uiso 1 1 calc R U
H27 H 0.7746 0.6252 1.0161 0.077 Uiso 1 1 calc R U
C3 C 0.6746(4) 0.7642(11) 0.8702(5) 0.039(2) Uani 1 1 d . .
C4 C 0.6157(3) 0.9507(10) 0.8363(4) 0.0333(19) Uani 1 1 d . .
H24 H 0.5822 0.9726 0.8671 0.040 Uiso 1 1 calc R U
H25 H 0.6427 1.1000 0.8358 0.040 Uiso 1 1 calc R U
C5 C 0.5059(4) 0.7499(9) 0.7514(5) 0.0299(19) Uani 1 1 d . .
C6 C 0.4877(4) 0.6717(10) 0.8183(4) 0.0343(19) Uani 1 1 d . .
H13 H 0.4699 0.8070 0.8404 0.041 Uiso 1 1 calc R U
H23 H 0.5351 0.6099 0.8549 0.041 Uiso 1 1 calc R U
C7 C 0.4256(3) 0.4833(10) 0.7995(4) 0.036(2) Uani 1 1 d . .
H21 H 0.3813 0.5364 0.7577 0.043 Uiso 1 1 calc R U
H22 H 0.4464 0.3398 0.7843 0.043 Uiso 1 1 calc R U
C8 C 0.3286(3) 0.5340(9) 0.8614(4) 0.033(2) Uani 1 1 d . .
C9 C 0.3287(4) 0.7281(11) 0.9043(5) 0.046(2) Uani 1 1 d . .
H20 H 0.3762 0.7932 0.9340 0.055 Uiso 1 1 calc R U
C10 C 0.2608(4) 0.8254(11) 0.9038(5) 0.052(3) Uani 1 1 d . .
H17 H 0.2613 0.9624 0.9318 0.062 Uiso 1 1 calc R U
C11 C 0.1909(4) 0.7272(11) 0.8631(5) 0.043(2) Uani 1 1 d . .
H2 H 0.1436 0.7920 0.8643 0.051 Uiso 1 1 calc R U
C12 C 0.5905(4) 0.9702(10) 0.6972(5) 0.040(2) Uani 1 1 d . .
C13 C 0.6065(4) 0.7595(10) 0.6566(5) 0.041(2) Uani 1 1 d . .
H6 H 0.6453 0.6601 0.6908 0.061 Uiso 1 1 calc R U
H4 H 0.6259 0.8118 0.6174 0.061 Uiso 1 1 calc R U
H5 H 0.5588 0.6705 0.6354 0.061 Uiso 1 1 calc R U
C14 C 0.6642(4) 1.1158(11) 0.7216(5) 0.045(2) Uani 1 1 d . .
H7 H 0.6560 1.2543 0.7480 0.068 Uiso 1 1 calc R U
H9 H 0.6776 1.1643 0.6784 0.068 Uiso 1 1 calc R U
H8 H 0.7063 1.0223 0.7539 0.068 Uiso 1 1 calc R U
C15 C 0.5264(4) 1.1210(10) 0.6475(5) 0.044(2) Uani 1 1 d . .
H10 H 0.4795 1.0272 0.6280 0.067 Uiso 1 1 calc R U
H11 H 0.5423 1.1807 0.6070 0.067 Uiso 1 1 calc R U
H12 H 0.5162 1.2522 0.6757 0.067 Uiso 1 1 calc R U
C16 C 0.4438(4) 0.3009(10) 0.9182(4) 0.0301(19) Uani 1 1 d . .
C17 C 0.4168(4) 0.2656(11) 0.9813(5) 0.038(2) Uani 1 1 d . .
H14 H 0.4471 0.1416 1.0125 0.057 Uiso 1 1 calc R U
H16 H 0.3622 0.2208 0.9639 0.057 Uiso 1 1 calc R U
H15 H 0.4229 0.4107 1.0095 0.057 Uiso 1 1 calc R U
C18 C 0.1916(4) 0.5361(12) 0.8215(5) 0.044(2) Uani 1 1 d . .
H18 H 0.1440 0.4704 0.7923 0.053 Uiso 1 1 calc R U
C19 C 0.2592(4) 0.4357(11) 0.8206(5) 0.042(2) Uani 1 1 d . .
H19 H 0.2583 0.2998 0.7921 0.050 Uiso 1 1 calc R U
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
C3 O1 C2 118.7(6)
C5 N1 C4 119.1(6)
C5 N1 C12 119.7(6)
C4 N1 C12 120.9(5)
C16 N2 C8 121.9(7)
C16 N2 C7 120.5(6)
C8 N2 C7 117.4(6)
O1 C2 C1 107.8(7)
O2 C3 O1 124.3(6)
O2 C3 C4 125.6(7)
O1 C3 C4 110.1(5)
N1 C4 C3 112.6(5)
O3 C5 N1 122.6(7)
O3 C5 C6 120.0(6)
N1 C5 C6 117.4(6)
C5 C6 C7 111.3(6)
N2 C7 C6 112.0(6)
C19 C8 C9 119.4(6)
C19 C8 N2 119.8(6)
C9 C8 N2 120.8(5)
C10 C9 C8 120.0(6)
C9 C10 C11 120.8(7)
C18 C11 C10 118.6(6)
N1 C12 C13 110.2(5)
N1 C12 C15 109.1(6)
C13 C12 C15 111.4(7)
N1 C12 C14 111.1(6)
C13 C12 C14 107.0(6)
C15 C12 C14 108.0(5)
O4 C16 N2 120.6(7)
O4 C16 C17 121.2(6)
N2 C16 C17 118.3(6)
C11 C18 C19 121.7(6)
C18 C19 C8 119.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.335(9)
O1 C2 1.467(9)
O2 C3 1.196(8)
O3 C5 1.239(8)
O4 C16 1.222(7)
N1 C5 1.364(8)
N1 C4 1.460(9)
N1 C12 1.497(11)
N2 C16 1.361(9)
N2 C8 1.428(8)
N2 C7 1.446(10)
C1 C2 1.497(11)
C3 C4 1.509(9)
C5 C6 1.502(11)
C6 C7 1.525(8)
C8 C19 1.380(9)
C8 C9 1.385(10)
C9 C10 1.362(9)
C10 C11 1.387(10)
C11 C18 1.359(10)
C12 C13 1.519(10)
C12 C15 1.521(10)
C12 C14 1.527(9)
C16 C17 1.468(11)
C18 C19 1.372(9)
