#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/70/1507035.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_1507035
loop_
_publ_author_name
'Giovannoni, Jérôme'
'Didierjean, Claude'
'Durand, Philippe'
'Marraud, Michel'
'Aubry, André'
'Renaut, Patrice'
'Martinez, Jean'
'Amblard, Muriel'
_publ_section_title
;
 Synthesis and structure of symmetrical bicyclic hexapeptides bridged by
 metathesis reaction.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              3449
_journal_page_last               3452
_journal_paper_doi               10.1021/ol0487940
_journal_volume                  6
_journal_year                    2004
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C36 H42 N6 O6, 5H2O'
_chemical_formula_sum            'C36 H52 N6 O11'
_chemical_formula_weight         744.84
_chemical_name_systematic
; 
(20E,1S,4R,7S,10S,13R,16S)-4,13-dibenzyl-7,8,16,17-
di(propane-1,3-diyl)-2,5,8,11,14,17-hexaaza-
bicyclo[8.8.4]docos-20-ene-3,6,9,12,15,18-hexaone
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2004-03-05T14:43:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.4080(10)
_cell_length_b                   15.8690(10)
_cell_length_c                   9.5910(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.76
_cell_measurement_theta_min      7.95
_cell_measurement_wavelength     1.5406
_cell_volume                     2040.7(3)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'WebLab ViewerPro 3.5 (MSI, 1999)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR_92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Mach3 diffractometer'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Nonius FR591 rotating Cu anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2148
_diffrn_reflns_theta_full        69.51
_diffrn_reflns_theta_max         69.51
_diffrn_reflns_theta_min         4.31
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.75
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.08
_refine_ls_abs_structure_details
;
The absolute conformation was not determined 
from the diffraction experiment since it was known 
from the synthetic experiment.
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2148
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.22
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1231P)²+0.6136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1731
_reflns_number_gt                2021
_reflns_number_total             2148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0487940si20040624_093911.cif
_cod_data_source_block           shelxl
_cod_database_code               1507035
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6613(2) 0.84210(18) 0.8143(3) 0.0371(7) Uani 1 1 d . . .
C1 C 0.6099(3) 0.7698(2) 0.7497(4) 0.0388(8) Uani 1 1 d . . .
H1A H 0.617 0.7716 0.648 0.05 Uiso 1 1 calc R . .
C2 C 0.6657(3) 0.6931(2) 0.8101(5) 0.0483(10) Uani 1 1 d . . .
H2A H 0.6321 0.6717 0.8923 0.063 Uiso 1 1 calc R . .
H2B H 0.6706 0.6483 0.7417 0.063 Uiso 1 1 calc R . .
C3 C 0.7683(3) 0.7271(2) 0.8470(5) 0.0497(10) Uani 1 1 d . . .
H3A H 0.8112 0.7288 0.7656 0.065 Uiso 1 1 calc R . .
H3B H 0.7997 0.6929 0.9184 0.065 Uiso 1 1 calc R . .
C4 C 0.7466(3) 0.8161(2) 0.9009(5) 0.0494(10) Uani 1 1 d . . .
H4A H 0.7292 0.8154 0.999 0.064 Uiso 1 1 calc R . .
H4B H 0.8034 0.8531 0.8871 0.064 Uiso 1 1 calc R . .
C5 C 0.4996(3) 0.7695(2) 0.7907(3) 0.0351(7) Uani 1 1 d . . .
O1 O 0.47339(19) 0.7617(2) 0.9135(3) 0.0519(8) Uani 1 1 d . . .
N2 N 0.4332(2) 0.77842(18) 0.6885(3) 0.0348(7) Uani 1 1 d D . .
H2 H 0.4535 0.7842 0.604 0.045 Uiso 1 1 calc RD . .
C6 C 0.3270(3) 0.7786(2) 0.7177(4) 0.0359(8) Uani 1 1 d . . .
H6A H 0.3159 0.7355 0.7892 0.047 Uiso 1 1 calc R . .
C7 C 0.2680(3) 0.7505(2) 0.5889(4) 0.0405(8) Uani 1 1 d . . .
H7A H 0.1975 0.7599 0.6053 0.053 Uiso 1 1 calc R . .
H7B H 0.2878 0.7847 0.5098 0.053 Uiso 1 1 calc R . .
C8 C 0.2845(3) 0.6592(2) 0.5546(4) 0.0424(9) Uani 1 1 d . . .
C9 C 0.2321(3) 0.5962(3) 0.6251(6) 0.0574(11) Uani 1 1 d . . .
H9A H 0.1854 0.6113 0.6924 0.075 Uiso 1 1 calc R . .
C10 C 0.2479(4) 0.5131(3) 0.5972(7) 0.0732(15) Uani 1 1 d . . .
H10A H 0.2126 0.4723 0.6463 0.095 Uiso 1 1 calc R . .
C11 C 0.3149(5) 0.4890(3) 0.4982(7) 0.0828(19) Uani 1 1 d . . .
H11A H 0.3246 0.4321 0.4791 0.108 Uiso 1 1 calc R . .
C12 C 0.3691(5) 0.5501(4) 0.4252(7) 0.0768(16) Uani 1 1 d . . .
H12A H 0.415 0.5342 0.3575 0.1 Uiso 1 1 calc R . .
C13 C 0.3538(4) 0.6340(3) 0.4546(5) 0.0589(12) Uani 1 1 d . . .
H13A H 0.3903 0.6747 0.4069 0.077 Uiso 1 1 calc R . .
C14 C 0.2873(3) 0.8615(2) 0.7782(4) 0.0377(8) Uani 1 1 d . . .
O2 O 0.2025(2) 0.86323(18) 0.8261(4) 0.0571(9) Uani 1 1 d . . .
N3 N 0.3468(2) 0.92851(18) 0.7794(4) 0.0387(7) Uani 1 1 d D B .
H3 H 0.403 0.9263 0.7365 0.05 Uiso 1 1 calc RD . .
C15 C 0.3187(3) 1.0057(2) 0.8518(4) 0.0396(8) Uani 1 1 d . . .
H15A H 0.2459 1.0113 0.8507 0.052 Uiso 1 1 calc R A 1
C16 C 0.3556(3) 1.0034(3) 1.0065(4) 0.0489(10) Uani 0.42(3) 1 d P B 1
H16A H 0.3155 1.0415 1.0621 0.064 Uiso 0.42(3) 1 calc PR B 1
H16B H 0.347 0.947 1.0435 0.064 Uiso 0.42(3) 1 calc PR B 1
C17 C 0.4613(16) 1.0278(13) 1.0175(14) 0.065(7) Uani 0.42(3) 1 d P . 1
H17 H 0.4761 1.0849 1.025 0.085 Uiso 0.42(3) 1 calc PR B 1
C18 C 0.3556(3) 1.0034(3) 1.0065(4) 0.0489(10) Uani 0.58(3) 1 d P B 2
H18A H 0.3506 1.0594 1.0464 0.064 Uiso 0.58(3) 1 calc PR B 2
H18B H 0.313 0.9661 1.0601 0.064 Uiso 0.58(3) 1 calc PR B 2
C19 C 0.4614(9) 0.9736(8) 1.0168(7) 0.043(4) Uani 0.58(3) 1 d P . 2
H19 H 0.4736 0.9161 1.0234 0.056 Uiso 0.58(3) 1 calc PR B 2
C20 C 0.3648(2) 1.0801(2) 0.7753(4) 0.0337(7) Uani 1 1 d . . .
O3 O 0.43025(19) 1.06915(15) 0.6870(3) 0.0420(6) Uani 1 1 d D . .
O4 O 0.4708(3) 0.8258(3) 0.4046(4) 0.0800(12) Uani 1 1 d D . .
O5 O 0.5504(5) 0.7535(5) 0.1782(4) 0.150(3) Uani 1 1 d D . .
O6 O 0.5 1 0.4396(5) 0.0726(14) Uani 1 2 d SD . .
H41 H 0.4653 0.887 0.3818 0.094 Uiso 1 1 d D . .
H42 H 0.5036 0.7965 0.3242 0.094 Uiso 1 1 d D . .
H51 H 0.608 0.7121 0.1747 0.094 Uiso 1 1 d D . .
H52 H 0.5151 0.7523 0.0856 0.094 Uiso 1 1 d D . .
H6 H 0.4421 1.0143 0.5035 0.094 Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 1 3
2 1 1
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
C20 N1 C4 128.4(3) 2_675 .
C20 N1 C1 118.5(3) 2_675 .
C4 N1 C1 112.5(3) . .
N1 C1 C5 110.3(3) . .
N1 C1 C2 103.2(3) . .
C5 C1 C2 111.7(3) . .
N1 C1 H1A 110.5 . .
C5 C1 H1A 110.5 . .
C2 C1 H1A 110.5 . .
C3 C2 C1 104.3(3) . .
C3 C2 H2A 110.9 . .
C1 C2 H2A 110.9 . .
C3 C2 H2B 110.9 . .
C1 C2 H2B 110.9 . .
H2A C2 H2B 108.9 . .
C2 C3 C4 103.6(3) . .
C2 C3 H3A 111 . .
C4 C3 H3A 111 . .
C2 C3 H3B 111.1 . .
C4 C3 H3B 111 . .
H3A C3 H3B 109 . .
N1 C4 C3 102.4(3) . .
N1 C4 H4A 111.3 . .
C3 C4 H4A 111.3 . .
N1 C4 H4B 111.3 . .
C3 C4 H4B 111.3 . .
H4A C4 H4B 109.2 . .
O1 C5 N2 121.5(3) . .
O1 C5 C1 121.4(3) . .
N2 C5 C1 117.2(3) . .
C5 N2 C6 121.0(3) . .
C5 N2 H2 119.5 . .
C6 N2 H2 119.5 . .
N2 C6 C14 114.6(3) . .
N2 C6 C7 110.5(3) . .
C14 C6 C7 112.1(3) . .
N2 C6 H6A 106.4 . .
C14 C6 H6A 106.4 . .
C7 C6 H6A 106.4 . .
C8 C7 C6 112.4(3) . .
C8 C7 H7A 109.1 . .
C6 C7 H7A 109.1 . .
C8 C7 H7B 109.1 . .
C6 C7 H7B 109.1 . .
H7A C7 H7B 107.9 . .
C13 C8 C9 117.6(4) . .
C13 C8 C7 121.7(4) . .
C9 C8 C7 120.7(4) . .
C10 C9 C8 121.3(5) . .
C10 C9 H9A 119.3 . .
C8 C9 H9A 119.3 . .
C9 C10 C11 120.7(5) . .
C9 C10 H10A 119.6 . .
C11 C10 H10A 119.6 . .
C10 C11 C12 119.8(5) . .
C10 C11 H11A 120.1 . .
C12 C11 H11A 120.1 . .
C13 C12 C11 119.3(6) . .
C13 C12 H12A 120.3 . .
C11 C12 H12A 120.3 . .
C12 C13 C8 121.2(5) . .
C12 C13 H13A 119.4 . .
C8 C13 H13A 119.4 . .
O2 C14 N3 122.3(3) . .
O2 C14 C6 118.9(3) . .
N3 C14 C6 118.8(3) . .
C14 N3 C15 121.4(3) . .
C14 N3 H3 119.3 . .
C15 N3 H3 119.3 . .
N3 C15 C20 108.5(3) . .
N3 C15 C16 110.5(3) . .
C20 C15 C16 110.2(3) . .
N3 C15 H15A 109.2 . .
C20 C15 H15A 109.2 . .
C16 C15 H15A 109.2 . .
C17 C16 C15 111.5(6) . .
C17 C16 H16A 109.3 . .
C15 C16 H16A 109.3 . .
C17 C16 H16B 109.3 . .
C15 C16 H16B 109.3 . .
H16A C16 H16B 108 . .
C17 C17 C16 124(2) 2_675 .
C17 C17 H17 117.9 2_675 .
C16 C17 H17 117.9 . .
C19 C19 H19 118.7 2_675 .
O3 C20 N1 120.7(3) . 2_675
O3 C20 C15 120.8(3) . .
N1 C20 C15 118.3(3) 2_675 .
H41 O4 H42 108.3 . .
H51 O5 H52 108.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C20 1.336(4) 2_675
N1 C4 1.472(5) .
N1 C1 1.475(4) .
C1 C5 1.531(5) .
C1 C2 1.542(5) .
C1 H1A 0.98 .
C2 C3 1.518(6) .
C2 H2A 0.97 .
C2 H2B 0.97 .
C3 C4 1.532(5) .
C3 H3A 0.97 .
C3 H3B 0.97 .
C4 H4A 0.97 .
C4 H4B 0.97 .
C5 O1 1.235(4) .
C5 N2 1.332(5) .
N2 C6 1.451(4) .
N2 H2 0.86 .
C6 C14 1.532(5) .
C6 C7 1.533(5) .
C6 H6A 0.98 .
C7 C8 1.502(5) .
C7 H7A 0.97 .
C7 H7B 0.97 .
C8 C13 1.393(6) .
C8 C9 1.397(6) .
C9 C10 1.363(7) .
C9 H9A 0.93 .
C10 C11 1.362(9) .
C10 H10A 0.93 .
C11 C12 1.399(9) .
C11 H11A 0.93 .
C12 C13 1.377(6) .
C12 H12A 0.93 .
C13 H13A 0.93 .
C14 O2 1.226(5) .
C14 N3 1.329(5) .
N3 C15 1.458(4) .
N3 H3 0.86 .
C15 C20 1.522(5) .
C15 C16 1.565(5) .
C15 H15A 0.98 .
C16 C17 1.47(2) .
C16 H16A 0.97 .
C16 H16B 0.97 .
C17 C17 1.36(5) 2_675
C17 H17 0.93 .
C19 C19 1.33(2) 2_675
C19 H19 0.93 .
C20 O3 1.231(4) .
C20 N1 1.336(4) 2_675
O4 H41 1.000 .
O4 H42 1.002 .
O5 H51 1.015 .
O5 H52 1.006 .
O6 H6 1.015 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O4 0.86 2.04 2.869(5) 162.8 .
N3 H3 O3 0.86 2.29 3.118(4) 162.9 2_675
O4 H41 O6 1.000 1.9328 2.813(4) 145.3 .
O4 H42 O5 1.002 1.680 2.678(5) 173.8 .
O5 H51 O2 1.015 1.742 2.756(5) 176.6 3_566
O5 H52 O1 1.006 1.750 2.744(4) 168.9 1_554
O6 H6 O3 1.015 1.970 2.777(5) 134.5 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C20 N1 C1 C5 -65.3(4) 2_675 . .
C4 N1 C1 C5 123.0(3) . . .
C20 N1 C1 C2 175.3(3) 2_675 . .
C4 N1 C1 C2 3.6(4) . . .
N1 C1 C2 C3 -25.2(4) . . .
C5 C1 C2 C3 -143.6(3) . . .
C1 C2 C3 C4 37.2(5) . . .
C20 N1 C4 C3 -151.5(4) 2_675 . .
C1 N1 C4 C3 19.1(4) . . .
C2 C3 C4 N1 -34.2(4) . . .
N1 C1 C5 O1 -62.5(5) . . .
C2 C1 C5 O1 51.7(5) . . .
N1 C1 C5 N2 117.2(3) . . .
C2 C1 C5 N2 -128.7(3) . . .
O1 C5 N2 C6 -0.5(5) . . .
C1 C5 N2 C6 179.9(3) . . .
C5 N2 C6 C14 77.5(4) . . .
C5 N2 C6 C7 -154.8(3) . . .
N2 C6 C7 C8 68.1(4) . . .
C14 C6 C7 C8 -162.8(3) . . .
C6 C7 C8 C13 -96.9(4) . . .
C6 C7 C8 C9 81.6(5) . . .
C13 C8 C9 C10 0.0(7) . . .
C7 C8 C9 C10 -178.5(5) . . .
C8 C9 C10 C11 -0.7(8) . . .
C9 C10 C11 C12 0.8(8) . . .
C10 C11 C12 C13 -0.1(8) . . .
C11 C12 C13 C8 -0.7(8) . . .
C9 C8 C13 C12 0.8(7) . . .
C7 C8 C13 C12 179.2(5) . . .
N2 C6 C14 O2 -168.7(4) . . .
C7 C6 C14 O2 64.4(5) . . .
N2 C6 C14 N3 9.9(5) . . .
C7 C6 C14 N3 -117.0(4) . . .
O2 C14 N3 C15 6.9(6) . . .
C6 C14 N3 C15 -171.7(3) . . .
C14 N3 C15 C20 -149.2(3) . . .
C14 N3 C15 C16 89.8(4) . . .
N3 C15 C16 C17 81.9(10) . . .
C20 C15 C16 C17 -38.0(10) . . .
C15 C16 C17 C17 -93.7(7) . . 2_675
N3 C15 C20 O3 -13.4(4) . . .
C16 C15 C20 O3 107.8(4) . . .
N3 C15 C20 N1 172.0(3) . . 2_675
C16 C15 C20 N1 -66.8(4) . . 2_675
C16 C17 C17 C16 170.0(14) . 2_675 2_675
C18 C19 C19 C18 -171.1(8) . 2_675 2_675
C15 C20 N1 C1 174.4(3) . 2_675 2_675
N3 C15 C18 C19 45.6(6) . . .
C15 C18 C19 C19 92.4(4) . . 2_675
