#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/37/4023795.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_4023795
loop_
_publ_author_name
'Arnaud Salaün'
'Clémence Mocquet'
'Romain Perochon'
'Aurélien Lecorgne'
'Barbara Le Grel'
'Michel Potel'
'Philippe Le Grel'
_publ_section_title
;
 Aza-β³-cyclotetrapeptides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8579
_journal_page_last               8582
_journal_paper_doi               10.1021/jo8013963
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C27 H38 N8 O5'
_chemical_formula_weight         554.65
_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                93.015(2)
_cell_angle_beta                 105.207(2)
_cell_angle_gamma                109.4140(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7804(2)
_cell_length_b                   11.7723(3)
_cell_length_c                   15.3624(4)
_cell_measurement_temperature    566(2)
_cell_volume                     1428.06(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      566(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25505
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0085(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.0897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                4360
_reflns_number_total             6536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8013963_si_001.cif
_cod_data_source_block           cyclo_3enk
_cod_database_code               4023795
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 0.701(2) 0.0408(14) 0.3264(10) 0.035(4) Uiso 1 1 d . . .
H3 H 0.871(2) 0.3190(16) 0.2645(12) 0.050(5) Uiso 1 1 d . . .
H2 H 0.889(2) 0.1337(16) 0.0910(11) 0.041(5) Uiso 1 1 d . . .
H8 H 0.965(2) -0.0485(15) 0.2400(12) 0.043(5) Uiso 1 1 d . . .
H1 H 0.128(4) -0.536(3) 0.265(2) 0.141(11) Uiso 1 1 d . . .
C1 C 0.3640(2) -0.33357(14) 0.31938(11) 0.0418(4) Uani 1 1 d . . .
H1A H 0.3992 -0.3945 0.3007 0.050 Uiso 1 1 calc R . .
C16 C 0.78245(19) 0.43359(14) 0.01260(11) 0.0392(4) Uani 1 1 d . . .
C18 C 0.8398(2) 0.32643(14) 0.02200(11) 0.0424(4) Uani 1 1 d . . .
H18A H 0.7661 0.2608 -0.0274 0.051 Uiso 1 1 calc R . .
H18B H 0.9534 0.3500 0.0165 0.051 Uiso 1 1 calc R . .
C11 C 0.8099(2) 0.35825(14) 0.41871(11) 0.0430(4) Uani 1 1 d . . .
H11A H 0.8981 0.4272 0.4086 0.052 Uiso 1 1 calc R . .
H11B H 0.8395 0.3541 0.4836 0.052 Uiso 1 1 calc R . .
C6 C 0.4817(2) -0.21677(14) 0.35251(11) 0.0412(4) Uani 1 1 d . . .
C2 C 0.1954(2) -0.36145(16) 0.31357(11) 0.0462(4) Uani 1 1 d . . .
C7 C 0.6667(2) -0.19327(15) 0.36261(12) 0.0466(4) Uani 1 1 d . . .
H7A H 0.7307 -0.1602 0.4259 0.056 Uiso 1 1 calc R . .
H7B H 0.6782 -0.2710 0.3497 0.056 Uiso 1 1 calc R . .
C12 C 1.1245(2) -0.06390(16) 0.11454(13) 0.0531(5) Uani 1 1 d . . .
H12A H 1.0421 -0.1399 0.0803 0.080 Uiso 1 1 calc R . .
H12B H 1.1925 -0.0787 0.1696 0.080 Uiso 1 1 calc R . .
H12C H 1.1954 -0.0250 0.0785 0.080 Uiso 1 1 calc R . .
C10 C 0.6448(2) 0.38000(16) 0.39055(12) 0.0507(4) Uani 1 1 d . . .
H10 H 0.6144 0.3826 0.3248 0.061 Uiso 1 1 calc R . .
C17 C 0.7021(2) 0.45169(16) -0.07282(12) 0.0521(4) Uani 1 1 d . . .
H17 H 0.6770 0.3948 -0.1237 0.063 Uiso 1 1 calc R . .
C5 C 0.4266(2) -0.12719(16) 0.37886(13) 0.0536(5) Uani 1 1 d . . .
H5 H 0.5040 -0.0487 0.4024 0.064 Uiso 1 1 calc R . .
C3 C 0.1414(2) -0.27032(18) 0.33764(12) 0.0540(5) Uani 1 1 d . . .
H3A H 0.0275 -0.2876 0.3317 0.065 Uiso 1 1 calc R . .
C15 C 0.8171(2) 0.51952(16) 0.08674(12) 0.0510(4) Uani 1 1 d . . .
H15 H 0.8707 0.5089 0.1449 0.061 Uiso 1 1 calc R . .
C14 C 0.6943(2) 0.63872(19) -0.00903(17) 0.0658(6) Uani 1 1 d . . .
H14 H 0.6653 0.7075 -0.0161 0.079 Uiso 1 1 calc R . .
C4 C 0.2567(3) -0.15316(18) 0.37056(13) 0.0597(5) Uani 1 1 d . . .
H4 H 0.2205 -0.0918 0.3871 0.072 Uiso 1 1 calc R . .
C13 C 0.7729(3) 0.62109(17) 0.07551(15) 0.0627(5) Uani 1 1 d . . .
H13 H 0.7970 0.6781 0.1261 0.075 Uiso 1 1 calc R . .
C8 C 0.5038(2) 0.2800(2) 0.40999(14) 0.0674(6) Uani 1 1 d . . .
H8A H 0.4012 0.2968 0.3913 0.101 Uiso 1 1 calc R . .
H8B H 0.5322 0.2761 0.4742 0.101 Uiso 1 1 calc R . .
H8C H 0.4881 0.2035 0.3769 0.101 Uiso 1 1 calc R . .
C9 C 0.6727(3) 0.5042(2) 0.44068(17) 0.0853(7) Uani 1 1 d . . .
H9A H 0.5691 0.5199 0.4238 0.128 Uiso 1 1 calc R . .
H9B H 0.7587 0.5664 0.4243 0.128 Uiso 1 1 calc R . .
H9C H 0.7076 0.5042 0.5054 0.128 Uiso 1 1 calc R . .
C19 C 0.6586(2) 0.55467(19) -0.08303(16) 0.0657(6) Uani 1 1 d . . .
H19 H 0.6048 0.5662 -0.1408 0.079 Uiso 1 1 calc R . .
N2 N 0.92810(16) 0.20070(12) 0.12214(9) 0.0361(3) Uani 1 1 d . . .
N3 N 0.79508(16) 0.26018(12) 0.27736(8) 0.0368(3) Uani 1 1 d . . .
N6 N 0.77755(16) 0.01179(11) 0.33701(9) 0.0371(3) Uani 1 1 d . . .
N8 N 0.92585(16) -0.04327(11) 0.18644(10) 0.0373(3) Uani 1 1 d . . .
C23 C 0.66064(17) 0.19065(13) 0.20848(10) 0.0335(3) Uani 1 1 d . . .
C21 C 0.93633(18) 0.08718(14) 0.37966(10) 0.0377(3) Uani 1 1 d . . .
C25 C 1.07695(18) 0.22978(14) 0.18536(10) 0.0368(4) Uani 1 1 d . . .
C27 C 0.75874(19) -0.08020(13) 0.14807(11) 0.0384(4) Uani 1 1 d . . .
O5 O 0.53907(12) 0.10943(10) 0.21845(7) 0.0452(3) Uani 1 1 d . . .
O3 O 0.69140(14) -0.06906(11) 0.07012(8) 0.0532(3) Uani 1 1 d . . .
O4 O 1.15118(14) 0.32726(10) 0.23757(8) 0.0508(3) Uani 1 1 d . . .
O2 O 1.06006(14) 0.05684(11) 0.39422(9) 0.0551(3) Uani 1 1 d . . .
O1 O 0.07980(16) -0.47711(13) 0.28625(10) 0.0657(4) Uani 1 1 d . . .
N1 N 0.83903(15) 0.28184(11) 0.10988(8) 0.0352(3) Uani 1 1 d . . .
N7 N 1.03836(15) 0.01505(11) 0.13761(9) 0.0380(3) Uani 1 1 d . . .
N4 N 0.80560(15) 0.24648(11) 0.36945(8) 0.0357(3) Uani 1 1 d . . .
N5 N 0.74502(15) -0.11059(11) 0.30494(9) 0.0392(3) Uani 1 1 d . . .
C22 C 0.66685(18) 0.21840(14) 0.11410(10) 0.0391(4) Uani 1 1 d . . .
H22A H 0.6165 0.1426 0.0717 0.047 Uiso 1 1 calc R . .
H22B H 0.5995 0.2683 0.0946 0.047 Uiso 1 1 calc R . .
C26 C 0.65183(19) -0.13945(14) 0.20805(11) 0.0423(4) Uani 1 1 d . . .
H26A H 0.5561 -0.1128 0.1981 0.051 Uiso 1 1 calc R . .
H26B H 0.6081 -0.2272 0.1900 0.051 Uiso 1 1 calc R . .
C24 C 1.15547(18) 0.13327(14) 0.18989(12) 0.0418(4) Uani 1 1 d . . .
H24B H 1.2524 0.1603 0.1668 0.050 Uiso 1 1 calc R . .
H24A H 1.1958 0.1237 0.2532 0.050 Uiso 1 1 calc R . .
C20 C 0.95473(19) 0.21609(14) 0.41095(11) 0.0408(4) Uani 1 1 d . . .
H20A H 0.9780 0.2281 0.4768 0.049 Uiso 1 1 calc R . .
H20B H 1.0513 0.2720 0.3967 0.049 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.47(15) . . ?
C15 C16 C17 118.35(16) . . ?
C15 C16 C18 121.75(14) . . ?
C17 C16 C18 119.78(15) . . ?
N1 C18 C16 112.60(12) . . ?
N4 C11 C10 113.86(13) . . ?
C5 C6 C1 118.41(15) . . ?
C5 C6 C7 122.41(15) . . ?
C1 C6 C7 119.11(14) . . ?
O1 C2 C3 118.28(16) . . ?
O1 C2 C1 122.27(16) . . ?
C3 C2 C1 119.44(16) . . ?
N5 C7 C6 117.00(13) . . ?
C8 C10 C11 111.79(15) . . ?
C8 C10 C9 111.40(17) . . ?
C11 C10 C9 108.01(16) . . ?
C16 C17 C19 120.29(18) . . ?
C6 C5 C4 120.65(17) . . ?
C2 C3 C4 119.94(16) . . ?
C16 C15 C13 120.67(18) . . ?
C13 C14 C19 119.46(18) . . ?
C3 C4 C5 120.02(17) . . ?
C14 C13 C15 120.7(2) . . ?
C14 C19 C17 120.52(19) . . ?
C25 N2 N1 121.61(13) . . ?
C23 N3 N4 121.72(12) . . ?
C21 N6 N5 120.11(13) . . ?
C27 N8 N7 120.53(14) . . ?
O5 C23 N3 124.10(14) . . ?
O5 C23 C22 120.58(13) . . ?
N3 C23 C22 115.32(12) . . ?
O2 C21 N6 124.22(15) . . ?
O2 C21 C20 120.70(14) . . ?
N6 C21 C20 115.08(13) . . ?
O4 C25 N2 124.88(15) . . ?
O4 C25 C24 120.00(14) . . ?
N2 C25 C24 115.13(13) . . ?
O3 C27 N8 124.22(14) . . ?
O3 C27 C26 120.35(14) . . ?
N8 C27 C26 115.43(14) . . ?
N2 N1 C22 108.87(11) . . ?
N2 N1 C18 109.06(11) . . ?
C22 N1 C18 112.12(12) . . ?
N8 N7 C24 109.70(11) . . ?
N8 N7 C12 110.51(12) . . ?
C24 N7 C12 112.91(12) . . ?
N3 N4 C20 109.52(11) . . ?
N3 N4 C11 109.69(12) . . ?
C20 N4 C11 111.93(12) . . ?
N6 N5 C26 109.79(12) . . ?
N6 N5 C7 111.51(12) . . ?
C26 N5 C7 114.96(12) . . ?
N1 C22 C23 113.24(12) . . ?
N5 C26 C27 113.14(12) . . ?
N7 C24 C25 113.19(12) . . ?
N4 C20 C21 114.01(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(2) . ?
C1 C6 1.387(2) . ?
C16 C15 1.381(2) . ?
C16 C17 1.382(2) . ?
C16 C18 1.506(2) . ?
C18 N1 1.4749(19) . ?
C11 N4 1.4670(19) . ?
C11 C10 1.511(2) . ?
C6 C5 1.381(2) . ?
C6 C7 1.517(2) . ?
C2 O1 1.363(2) . ?
C2 C3 1.379(3) . ?
C7 N5 1.4734(19) . ?
C12 N7 1.461(2) . ?
C10 C8 1.507(3) . ?
C10 C9 1.528(3) . ?
C17 C19 1.392(3) . ?
C5 C4 1.388(3) . ?
C3 C4 1.383(3) . ?
C15 C13 1.380(2) . ?
C14 C13 1.364(3) . ?
C14 C19 1.363(3) . ?
N2 C25 1.331(2) . ?
N2 N1 1.4133(17) . ?
N3 C23 1.3395(19) . ?
N3 N4 1.4148(17) . ?
N6 C21 1.3407(19) . ?
N6 N5 1.4063(18) . ?
N8 C27 1.336(2) . ?
N8 N7 1.4150(17) . ?
C23 O5 1.2246(16) . ?
C23 C22 1.514(2) . ?
C21 O2 1.2234(18) . ?
C21 C20 1.510(2) . ?
C25 O4 1.2315(18) . ?
C25 C24 1.508(2) . ?
C27 O3 1.2237(19) . ?
C27 C26 1.518(2) . ?
N1 C22 1.4675(18) . ?
N7 C24 1.4618(19) . ?
N4 C20 1.4651(19) . ?
N5 C26 1.457(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658780
