#------------------------------------------------------------------------------
#$Date: 2022-09-14 21:32:59 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277840 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/18/4021831.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_4021831
loop_
_publ_author_name
'Philippe Le Grel'
'Arnaud Salaün'
'Michel Potel'
'Barbara Le Grel'
'Fredéric Lassagne'
_publ_section_title
;
 Aza-β³-Cyclohexapeptides: Pseudopeptidic Macrocycles with
 Interesting Conformational and Configurational Properties
 Slow Pyramidal Nitrogen Inversion in 24-Membered Rings!
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5638
_journal_page_last               5645
_journal_paper_doi               10.1021/jo0608467
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C54 H60 N12 O6'
_chemical_formula_sum            'C54 H60 N12 O6'
_chemical_formula_weight         973.14
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2005-03-24T16:38:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                100.9323(11)
_cell_angle_beta                 109.3298(11)
_cell_angle_gamma                98.4297(13)
_cell_formula_units_Z            1
_cell_length_a                   9.8078(3)
_cell_length_b                   11.5104(3)
_cell_length_c                   12.6508(4)
_cell_measurement_reflns_used    5627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.263
_cell_measurement_wavelength     0.71073
_cell_volume                     1288.98(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.102741E-1
_diffrn_orient_matrix_UB_12      -0.215114E-1
_diffrn_orient_matrix_UB_13      0.748013E-1
_diffrn_orient_matrix_UB_21      -0.109347
_diffrn_orient_matrix_UB_22      -0.343774E-1
_diffrn_orient_matrix_UB_23      -0.299555E-1
_diffrn_orient_matrix_UB_31      0.155179E-1
_diffrn_orient_matrix_UB_32      -0.812783E-1
_diffrn_orient_matrix_UB_33      -0.318319E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8520
_diffrn_reflns_theta_full        25.69
_diffrn_reflns_theta_max         25.69
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.0780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1327
_reflns_number_gt                3398
_reflns_number_total             4877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0608467si20060418_105227.cif
_cod_database_code               4021831
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 0.17522(16) 0.81325(12) 0.43105(13) 0.0471(4) Uani 1 1 d .
O2 O 0.37647(12) 0.93637(11) 0.57986(10) 0.0541(3) Uani 1 1 d .
N3 N 0.20064(15) 0.90629(13) 0.79184(12) 0.0495(4) Uani 1 1 d .
N4 N 0.04147(15) 0.99820(14) 0.26249(12) 0.0496(4) Uani 1 1 d .
O5 O -0.09172(14) 0.81162(11) 0.24464(11) 0.0651(4) Uani 1 1 d .
N6 N 0.17763(15) 0.96289(12) 0.29125(11) 0.0474(4) Uani 1 1 d .
C7 C 0.28009(17) 0.91561(14) 0.48274(14) 0.0435(4) Uani 1 1 d .
O8 O -0.05977(13) 0.74662(12) 0.63727(11) 0.0654(4) Uani 1 1 d .
N9 N 0.18306(16) 0.83243(13) 0.68344(12) 0.0510(4) Uani 1 1 d .
N10 N 0.18259(16) 0.70948(11) 0.47575(12) 0.0494(4) Uani 1 1 d .
C11 C 0.2726(2) 1.01018(15) 0.41382(14) 0.0531(5) Uani 1 1 d .
H11A H 0.236 1.0755 0.4481 0.064 Uiso 1 1 calc R
H11B H 0.3721 1.0442 0.4196 0.064 Uiso 1 1 calc R
C12 C 0.2485(2) 0.97961(15) 0.20795(15) 0.0525(4) Uani 1 1 d .
H12A H 0.1923 0.9189 0.1355 0.063 Uiso 1 1 calc R
H12B H 0.3471 0.9642 0.2369 0.063 Uiso 1 1 calc R
C13 C 0.3241(2) 0.63951(14) 0.35629(15) 0.0542(5) Uani 1 1 d .
C14 C 0.1821(2) 1.11703(17) 0.07578(15) 0.0587(5) Uani 1 1 d .
H14 H 0.1226 1.0488 0.0172 0.07 Uiso 1 1 calc R
C15 C -0.22471(19) 0.96484(16) 0.20805(16) 0.0565(5) Uani 1 1 d .
H15A H -0.2907 0.9173 0.1312 0.068 Uiso 1 1 calc R
H15B H -0.2738 0.9525 0.2615 0.068 Uiso 1 1 calc R
C16 C 0.26223(18) 1.10308(14) 0.18299(14) 0.0469(4) Uani 1 1 d .
C17 C 0.05324(19) 0.75640(15) 0.61501(15) 0.0502(4) Uani 1 1 d .
C18 C -0.08427(18) 0.91822(15) 0.24150(14) 0.0493(4) Uani 1 1 d .
C19 C 0.0525(2) 0.67713(16) 0.50504(16) 0.0595(5) Uani 1 1 d .
H19A H 0.0429 0.594 0.5118 0.071 Uiso 1 1 calc R
H19B H -0.0346 0.6796 0.4413 0.071 Uiso 1 1 calc R
C20 C 0.4626(2) 0.63658(17) 0.43081(18) 0.0672(5) Uani 1 1 d .
H20 H 0.4713 0.6153 0.4997 0.081 Uiso 1 1 calc R
C21 C 0.1896(2) 0.60935(15) 0.38632(17) 0.0607(5) Uani 1 1 d .
H21A H 0.1012 0.5926 0.317 0.073 Uiso 1 1 calc R
H21B H 0.1913 0.5366 0.4144 0.073 Uiso 1 1 calc R
C22 C 0.3139(3) 0.67130(18) 0.25426(17) 0.0701(6) Uani 1 1 d .
H22 H 0.2222 0.6743 0.2028 0.084 Uiso 1 1 calc R
C23 C 0.3177(2) 0.87809(18) 0.88453(16) 0.0602(5) Uani 1 1 d .
H23A H 0.334 0.9331 0.9581 0.072 Uiso 1 1 calc R
H23B H 0.4094 0.8905 0.8704 0.072 Uiso 1 1 calc R
C24 C 0.2768(2) 0.74920(18) 0.89108(15) 0.0595(5) Uani 1 1 d .
C25 C 0.1882(2) 1.23029(19) 0.05337(18) 0.0698(6) Uani 1 1 d .
H25 H 0.1333 1.2374 -0.0198 0.084 Uiso 1 1 calc R
C26 C 0.1436(2) 0.70507(19) 0.89942(18) 0.0697(6) Uani 1 1 d .
H26 H 0.0783 0.7557 0.9016 0.084 Uiso 1 1 calc R
C27 C 0.2739(3) 1.33100(18) 0.13746(18) 0.0694(6) Uani 1 1 d .
H27 H 0.2766 1.4074 0.1229 0.083 Uiso 1 1 calc R
C28 C 0.3524(3) 1.20620(17) 0.26649(16) 0.0695(6) Uani 1 1 d .
H28 H 0.4111 1.1996 0.3388 0.083 Uiso 1 1 calc R
C29 C 0.3334(6) 0.5554(4) 0.8949(3) 0.1414(15) Uani 1 1 d .
H29 H 0.3992 0.5049 0.8947 0.17 Uiso 1 1 calc R
C30 C 0.3563(3) 1.31909(18) 0.24382(18) 0.0794(7) Uani 1 1 d .
H30 H 0.4159 1.3879 0.3017 0.095 Uiso 1 1 calc R
C31 C 0.1060(3) 0.5872(2) 0.9046(2) 0.0970(9) Uani 1 1 d .
H31 H 0.0159 0.5588 0.9108 0.116 Uiso 1 1 calc R
C32 C 0.5759(3) 0.6958(2) 0.3043(3) 0.0925(8) Uani 1 1 d .
H32 H 0.6603 0.7151 0.2871 0.111 Uiso 1 1 calc R
C33 C 0.5870(3) 0.6641(2) 0.4059(2) 0.0839(7) Uani 1 1 d .
H33 H 0.6788 0.6615 0.4575 0.101 Uiso 1 1 calc R
C34 C 0.4396(3) 0.6987(2) 0.2284(2) 0.0885(7) Uani 1 1 d .
H34 H 0.4316 0.7192 0.1593 0.106 Uiso 1 1 calc R
C35 C 0.3720(4) 0.6735(3) 0.8894(2) 0.1037(9) Uani 1 1 d .
H35 H 0.4629 0.702 0.8846 0.124 Uiso 1 1 calc R
C36 C 0.1999(6) 0.5116(3) 0.9008(3) 0.1212(13) Uani 1 1 d .
H36 H 0.1732 0.4311 0.9021 0.145 Uiso 1 1 calc R
H1 H 0.111(2) 0.8057(16) 0.3625(17) 0.054(5) Uiso 1 1 d .
H9 H 0.257(2) 0.8422(18) 0.6616(17) 0.064(6) Uiso 1 1 d .
H4 H 0.037(2) 1.0744(19) 0.2661(17) 0.067(6) Uiso 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.3
-1 0 0 0.3
0 1 0 0.015
0 -1 0 0.02
0 0 1 0.08
0 0 -1 0.08
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
C7 N1 N10 121.30(14) . .
C7 N1 H1 119.0(12) . .
N10 N1 H1 118.7(12) . .
N9 N3 C15 111.05(13) . 2_576
N9 N3 C23 109.80(14) . .
C15 N3 C23 113.77(13) 2_576 .
C18 N4 N6 120.42(14) . .
C18 N4 H4 117.4(13) . .
N6 N4 H4 121.7(13) . .
N4 N6 C11 113.50(14) . .
N4 N6 C12 111.57(12) . .
C11 N6 C12 116.04(13) . .
O2 C7 N1 124.54(14) . .
O2 C7 C11 120.31(14) . .
N1 C7 C11 115.14(14) . .
C17 N9 N3 121.09(15) . .
C17 N9 H9 121.8(13) . .
N3 N9 H9 117.0(13) . .
N1 N10 C19 109.69(14) . .
N1 N10 C21 107.98(13) . .
C19 N10 C21 111.00(13) . .
N6 C11 C7 113.79(13) . .
N6 C11 H11A 108.8 . .
C7 C11 H11A 108.8 . .
N6 C11 H11B 108.8 . .
C7 C11 H11B 108.8 . .
H11A C11 H11B 107.7 . .
N6 C12 C16 115.86(15) . .
N6 C12 H12A 108.3 . .
C16 C12 H12A 108.3 . .
N6 C12 H12B 108.3 . .
C16 C12 H12B 108.3 . .
H12A C12 H12B 107.4 . .
C20 C13 C22 118.1(2) . .
C20 C13 C21 120.52(17) . .
C22 C13 C21 121.40(18) . .
C16 C14 C25 121.42(17) . .
C16 C14 H14 119.3 . .
C25 C14 H14 119.3 . .
N3 C15 C18 114.08(13) 2_576 .
N3 C15 H15A 108.7 2_576 .
C18 C15 H15A 108.7 . .
N3 C15 H15B 108.7 2_576 .
C18 C15 H15B 108.7 . .
H15A C15 H15B 107.6 . .
C14 C16 C28 117.45(16) . .
C14 C16 C12 120.80(15) . .
C28 C16 C12 121.75(15) . .
O8 C17 N9 124.60(18) . .
O8 C17 C19 119.83(15) . .
N9 C17 C19 115.55(16) . .
O5 C18 N4 124.52(17) . .
O5 C18 C15 119.45(14) . .
N4 C18 C15 116.00(15) . .
N10 C19 C17 115.80(14) . .
N10 C19 H19A 108.3 . .
C17 C19 H19A 108.3 . .
N10 C19 H19B 108.3 . .
C17 C19 H19B 108.3 . .
H19A C19 H19B 107.4 . .
C33 C20 C13 121.8(2) . .
C33 C20 H20 119.1 . .
C13 C20 H20 119.1 . .
N10 C21 C13 112.04(13) . .
N10 C21 H21A 109.2 . .
C13 C21 H21A 109.2 . .
N10 C21 H21B 109.2 . .
C13 C21 H21B 109.2 . .
H21A C21 H21B 107.9 . .
C13 C22 C34 120.4(2) . .
C13 C22 H22 119.8 . .
C34 C22 H22 119.8 . .
N3 C23 C24 111.46(14) . .
N3 C23 H23A 109.3 . .
C24 C23 H23A 109.3 . .
N3 C23 H23B 109.3 . .
C24 C23 H23B 109.3 . .
H23A C23 H23B 108 . .
C35 C24 C26 118.6(2) . .
C35 C24 C23 120.6(2) . .
C26 C24 C23 120.77(18) . .
C27 C25 C14 120.33(18) . .
C27 C25 H25 119.8 . .
C14 C25 H25 119.8 . .
C31 C26 C24 120.7(2) . .
C31 C26 H26 119.6 . .
C24 C26 H26 119.6 . .
C25 C27 C30 119.25(18) . .
C25 C27 H27 120.4 . .
C30 C27 H27 120.4 . .
C16 C28 C30 120.71(18) . .
C16 C28 H28 119.6 . .
C30 C28 H28 119.6 . .
C36 C29 C35 120.8(3) . .
C36 C29 H29 119.6 . .
C35 C29 H29 119.6 . .
C27 C30 C28 120.80(19) . .
C27 C30 H30 119.6 . .
C28 C30 H30 119.6 . .
C36 C31 C26 120.4(3) . .
C36 C31 H31 119.8 . .
C26 C31 H31 119.8 . .
C34 C32 C33 119.6(2) . .
C34 C32 H32 120.2 . .
C33 C32 H32 120.2 . .
C20 C33 C32 119.8(2) . .
C20 C33 H33 120.1 . .
C32 C33 H33 120.1 . .
C32 C34 C22 120.3(2) . .
C32 C34 H34 119.8 . .
C22 C34 H34 119.8 . .
C24 C35 C29 120.2(3) . .
C24 C35 H35 119.9 . .
C29 C35 H35 119.9 . .
C31 C36 C29 119.2(3) . .
C31 C36 H36 120.4 . .
C29 C36 H36 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C7 1.334(2) .
N1 N10 1.4164(17) .
N1 H1 0.867(19) .
O2 C7 1.2304(19) .
N3 N9 1.411(2) .
N3 C15 1.467(2) 2_576
N3 C23 1.470(2) .
N4 C18 1.340(2) .
N4 N6 1.405(2) .
N4 H4 0.88(2) .
O5 C18 1.227(2) .
N6 C11 1.464(2) .
N6 C12 1.467(2) .
C7 C11 1.514(2) .
O8 C17 1.226(2) .
N9 C17 1.339(2) .
N9 H9 0.86(2) .
N10 C19 1.459(2) .
N10 C21 1.481(2) .
C11 H11A 0.97 .
C11 H11B 0.97 .
C12 C16 1.510(2) .
C12 H12A 0.97 .
C12 H12B 0.97 .
C13 C20 1.383(3) .
C13 C22 1.384(3) .
C13 C21 1.501(3) .
C14 C16 1.377(2) .
C14 C25 1.383(3) .
C14 H14 0.93 .
C15 N3 1.467(2) 2_576
C15 C18 1.510(3) .
C15 H15A 0.97 .
C15 H15B 0.97 .
C16 C28 1.380(2) .
C17 C19 1.509(3) .
C19 H19A 0.97 .
C19 H19B 0.97 .
C20 C33 1.366(3) .
C20 H20 0.93 .
C21 H21A 0.97 .
C21 H21B 0.97 .
C22 C34 1.385(3) .
C22 H22 0.93 .
C23 C24 1.504(3) .
C23 H23A 0.97 .
C23 H23B 0.97 .
C24 C35 1.369(3) .
C24 C26 1.376(3) .
C25 C27 1.355(3) .
C25 H25 0.93 .
C26 C31 1.373(3) .
C26 H26 0.93 .
C27 C30 1.366(3) .
C27 H27 0.93 .
C28 C30 1.381(3) .
C28 H28 0.93 .
C29 C36 1.363(5) .
C29 C35 1.379(5) .
C29 H29 0.93 .
C30 H30 0.93 .
C31 C36 1.362(5) .
C31 H31 0.93 .
C32 C34 1.374(4) .
C32 C33 1.376(4) .
C32 H32 0.93 .
C33 H33 0.93 .
C34 H34 0.93 .
C35 H35 0.93 .
C36 H36 0.93 .
