#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023258.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_4023258
loop_
_publ_author_name
'Philippe Le Grel'
'Arnaud Salaün'
'Clémence Mocquet'
'Barbara Le Grel'
'Thierry Roisnel'
'Michel Potel'
_publ_section_title
;
 Postsynthetic Modification of C₃-Symmetric
 Aza-β³-Cyclohexapeptides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1306
_journal_page_last               1310
_journal_paper_doi               10.1021/jo7021394
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C36 H63 N15 O9'
_chemical_formula_sum            'C36 H63 N15 O9'
_chemical_formula_weight         850.01
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      146
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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      2.3
_audit_creation_date             2007-09-12T16:12:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   18.5180(10)
_cell_length_b                   18.5180(10)
_cell_length_c                   13.4400(10)
_cell_measurement_reflns_used    7503
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      1.98
_cell_measurement_wavelength     0.71073
_cell_volume                     3991.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by SAINT Bruker-AXS'
_diffrn_orient_matrix_UB_11      0.199252E-1
_diffrn_orient_matrix_UB_12      -0.83103E-2
_diffrn_orient_matrix_UB_13      -0.658535E-1
_diffrn_orient_matrix_UB_21      -0.420726E-1
_diffrn_orient_matrix_UB_22      0.99898E-2
_diffrn_orient_matrix_UB_23      -0.344686E-1
_diffrn_orient_matrix_UB_31      0.414838E-1
_diffrn_orient_matrix_UB_32      0.60985E-1
_diffrn_orient_matrix_UB_33      -0.33275E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23506
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         2.96
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.061
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.3
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2026
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0414
_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)+(0.0987P)²+0.6763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                1933
_reflns_number_total             2026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7021394_si2.cif
_cod_data_source_block           c3isoallyl
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4023258
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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
O1 O 0.50131(11) 0.19784(11) 0.55042(11) 0.0283(4) Uani 1 1 d . . .
O2 O 0.63538(10) 0.15674(11) 0.26810(12) 0.0276(4) Uani 1 1 d . . .
O3 O 0.33873(10) 0.08468(11) 0.25172(13) 0.0286(4) Uani 1 1 d . . .
N4 N 0.45335(12) 0.15295(12) 0.35180(14) 0.0220(4) Uani 1 1 d . . .
C5 C 0.69609(13) 0.19326(14) 0.32382(16) 0.0222(4) Uani 1 1 d . . .
C6 C 0.53056(14) 0.16287(14) 0.50056(15) 0.0228(4) Uani 1 1 d . . .
N7 N 0.62594(12) 0.10811(12) 0.46539(14) 0.0242(4) Uani 1 1 d . . .
N8 N 0.50968(12) 0.13820(12) 0.40444(14) 0.0232(4) Uani 1 1 d . . .
H8 H 0.5324 0.1121 0.3745 0.028 Uiso 1 1 calc R . .
C9 C 0.37851(14) 0.08147(14) 0.32247(16) 0.0237(4) Uani 1 1 d . . .
N10 N 0.69751(11) 0.17363(12) 0.41950(14) 0.0234(4) Uani 1 1 d . . .
H10 H 0.7436 0.2019 0.4543 0.028 Uiso 1 1 calc R . .
N11 N 0.35515(13) 0.01369(12) 0.38026(17) 0.0310(5) Uani 1 1 d . . .
H11 H 0.3875 0.0161 0.4296 0.037 Uiso 1 1 calc R . .
C12 C 0.48964(15) 0.22345(14) 0.28328(15) 0.0242(5) Uani 1 1 d . . .
H12A H 0.4552 0.2075 0.2222 0.029 Uiso 1 1 calc R . .
H12B H 0.5459 0.2346 0.2641 0.029 Uiso 1 1 calc R . .
C13 C 0.59372(14) 0.14145(15) 0.54262(15) 0.0257(5) Uani 1 1 d . . .
H13A H 0.6408 0.1921 0.5722 0.031 Uiso 1 1 calc R . .
H13B H 0.5672 0.0996 0.5962 0.031 Uiso 1 1 calc R . .
C14 C 0.64369(16) 0.04301(16) 0.49988(18) 0.0294(5) Uani 1 1 d . . .
H14A H 0.6009 0.0067 0.5488 0.035 Uiso 1 1 calc R . .
H14B H 0.6987 0.0694 0.5334 0.035 Uiso 1 1 calc R . .
C15 C 0.6439(2) -0.00959(19) 0.4127(2) 0.0394(6) Uani 1 1 d . . .
H15 H 0.6762 0.0292 0.3571 0.047 Uiso 1 1 calc R . .
C16 C 0.27648(18) -0.06390(17) 0.3618(2) 0.0412(7) Uani 1 1 d . . .
H16A H 0.2366 -0.0504 0.3298 0.049 Uiso 1 1 calc R . .
H16B H 0.2523 -0.0913 0.4262 0.049 Uiso 1 1 calc R . .
C17 C 0.5557(2) -0.0671(2) 0.3758(2) 0.0484(8) Uani 1 1 d . . .
H17A H 0.5571 -0.1002 0.3197 0.073 Uiso 1 1 calc R . .
H17B H 0.5308 -0.0338 0.3543 0.073 Uiso 1 1 calc R . .
H17C H 0.5222 -0.1045 0.4298 0.073 Uiso 1 1 calc R . .
C18 C 0.6874(3) -0.0583(2) 0.4408(3) 0.0520(8) Uani 1 1 d . . .
H18A H 0.687 -0.0913 0.3836 0.078 Uiso 1 1 calc R . .
H18B H 0.6579 -0.0955 0.4966 0.078 Uiso 1 1 calc R . .
H18C H 0.7451 -0.0192 0.4603 0.078 Uiso 1 1 calc R . .
C19 C 0.2875(2) -0.1227(2) 0.2975(3) 0.0575(9) Uani 1 1 d . . .
H19 H 0.3258 -0.14 0.3174 0.069 Uiso 1 1 calc R . .
C20 C 0.2449(3) -0.1526(3) 0.2119(4) 0.0738(12) Uani 1 1 d . . .
H20A H 0.2064 -0.136 0.191 0.089 Uiso 1 1 calc R . .
H20B H 0.2535 -0.1902 0.1725 0.089 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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
N8 N4 C9 115.94(18) . . ?
N8 N4 C12 116.12(18) . . ?
C9 N4 C12 117.38(18) . . ?
O2 C5 N10 124.7(2) . . ?
O2 C5 C12 119.16(19) . 2_655 ?
N10 C5 C12 116.09(19) . 2_655 ?
O1 C6 N8 124.6(2) . . ?
O1 C6 C13 122.27(19) . . ?
N8 C6 C13 113.10(19) . . ?
N10 N7 C14 110.01(18) . . ?
N10 N7 C13 110.42(18) . . ?
C14 N7 C13 115.00(18) . . ?
C6 N8 N4 122.04(19) . . ?
C6 N8 H8 119 . . ?
N4 N8 H8 119 . . ?
O3 C9 N11 124.9(2) . . ?
O3 C9 N4 120.3(2) . . ?
N11 C9 N4 114.77(19) . . ?
C5 N10 N7 120.93(18) . . ?
C5 N10 H10 119.5 . . ?
N7 N10 H10 119.5 . . ?
C9 N11 C16 120.8(2) . . ?
C9 N11 H11 119.6 . . ?
C16 N11 H11 119.6 . . ?
N4 C12 C5 115.15(18) . 3_665 ?
N4 C12 H12A 108.5 . . ?
C5 C12 H12A 108.5 3_665 . ?
N4 C12 H12B 108.5 . . ?
C5 C12 H12B 108.5 3_665 . ?
H12A C12 H12B 107.5 . . ?
N7 C13 C6 111.85(17) . . ?
N7 C13 H13A 109.2 . . ?
C6 C13 H13A 109.2 . . ?
N7 C13 H13B 109.2 . . ?
C6 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N7 C14 C15 110.7(2) . . ?
N7 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N7 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C17 C15 C14 110.7(3) . . ?
C17 C15 C18 111.5(3) . . ?
C14 C15 C18 110.9(2) . . ?
C17 C15 H15 107.9 . . ?
C14 C15 H15 107.9 . . ?
C18 C15 H15 107.9 . . ?
N11 C16 C19 112.6(3) . . ?
N11 C16 H16A 109.1 . . ?
C19 C16 H16A 109.1 . . ?
N11 C16 H16B 109.1 . . ?
C19 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C16 122.1(4) . . ?
C20 C19 H19 118.9 . . ?
C16 C19 H19 118.9 . . ?
C19 C20 H20A 120 . . ?
C19 C20 H20B 120 . . ?
H20A C20 H20B 120 . . ?
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
O1 C6 1.230(3) . ?
O2 C5 1.234(3) . ?
O3 C9 1.222(3) . ?
N4 N8 1.396(3) . ?
N4 C9 1.412(3) . ?
N4 C12 1.458(3) . ?
C5 N10 1.340(3) . ?
C5 C12 1.526(3) 2_655 ?
C6 N8 1.360(3) . ?
C6 C13 1.520(3) . ?
N7 N10 1.415(3) . ?
N7 C14 1.474(3) . ?
N7 C13 1.477(3) . ?
N8 H8 0.88 . ?
C9 N11 1.350(3) . ?
N10 H10 0.88 . ?
N11 C16 1.468(3) . ?
N11 H11 0.88 . ?
C12 C5 1.526(3) 3_665 ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.525(4) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C17 1.520(5) . ?
C15 C18 1.526(5) . ?
C15 H15 1 . ?
C16 C19 1.482(5) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C20 1.347(6) . ?
C19 H19 0.95 . ?
C20 H20A 0.95 . ?
C20 H20B 0.95 . ?
