#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:39:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180231 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/17/7111764.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111764
loop_
_publ_author_name
'Krause, Martin R.'
'Goddard, Richard'
'Kubik, Stefan'
_publ_section_title
;
 Formation of a cyclic tetrapeptide mimic by thermal azide--alkyne
 1,3-dipolar cycloaddition
;
_journal_issue                   29
_journal_name_full               'Chemical Communications'
_journal_page_first              5307
_journal_page_last               5309
_journal_paper_doi               10.1039/c0cc01154a
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_compound_source        'sublimation at 260 degs C'
_chemical_formula_moiety         'C22 H22 N6 O4'
_chemical_formula_sum            'C22 H22 N6 O4'
_chemical_formula_weight         434.46
_chemical_melting_point          ?
_chemical_name_common            cylo-bis((L)-prolyl-alpha-6-amino-2-picolinyl)
_chemical_name_systematic
;
cylo-bis[(L)-prolyl-alpha-6-amino-2-picolinyl]
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                KUB-POHL-Tetr-Pept
_audit_creation_date             2010-04-13
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.138(4)
_cell_length_b                   11.325(5)
_cell_length_c                   19.715(8)
_cell_measurement_reflns_used    1005
_cell_measurement_temperature    293
_cell_measurement_theta_max      32.156
_cell_measurement_theta_min      2.918
_cell_volume                     2040.3(15)
_computing_cell_refinement       'SAINT V6.45a (Bruker AXS, 2000)'
_computing_data_collection       'SMART V5.631 (Bruker AXS, 2000)'
_computing_data_reduction        'SAINT V6.45a (Bruker AXS, 2000)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker AXS APEX1'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  Si-111
_diffrn_radiation_source         'SCD beamline, ANKA, Karlsruhe'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.0
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19076
_diffrn_reflns_theta_full        33.85
_diffrn_reflns_theta_max         33.85
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.632224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker AXS (2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.7217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                2661
_reflns_number_total             2848
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            C0CC01154Asup1.cif
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'none' was changed to '?' - the value
is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2040.3(14)
_cod_database_code               7111764
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
C1 C 0.7612(4) 0.2363(3) 0.79575(15) 0.0436(7) Uani 1 1 d . . .
C2 C 0.8912(3) 0.1576(3) 0.78153(17) 0.0495(9) Uani 1 1 d . B .
H2 H 0.9549 0.1529 0.8214 0.059 Uiso 1 1 calc R . .
C3 C 0.9756(5) 0.2051(4) 0.72059(19) 0.0707(12) Uani 1 1 d . . .
H3A H 0.9145 0.2590 0.6949 0.085 Uiso 1 1 calc R A 1
H3B H 1.0617 0.2476 0.7358 0.085 Uiso 1 1 calc R A 1
C4A C 1.0196(11) 0.1032(9) 0.6772(5) 0.069(2) Uani 0.50 1 d P B 1
H4A H 1.1135 0.0716 0.6911 0.083 Uiso 0.50 1 calc PR B 1
H4B H 1.0245 0.1257 0.6298 0.083 Uiso 0.50 1 calc PR B 1
C4B C 0.9274(13) 0.1380(9) 0.6647(4) 0.071(2) Uani 0.50 1 d P B 2
H4C H 1.0023 0.1363 0.6299 0.085 Uiso 0.50 1 calc PR B 2
H4D H 0.8395 0.1727 0.6456 0.085 Uiso 0.50 1 calc PR B 2
C5 C 0.8961(5) 0.0142(4) 0.68976(19) 0.0664(11) Uani 1 1 d . . .
H5A H 0.8168 0.0257 0.6577 0.080 Uiso 1 1 calc R C 1
H5B H 0.9319 -0.0661 0.6857 0.080 Uiso 1 1 calc R C 1
C6 C 0.7640(4) -0.0435(3) 0.79093(17) 0.0504(8) Uani 1 1 d . . .
C7 C 0.7145(4) -0.0298(3) 0.86311(17) 0.0460(8) Uani 1 1 d . B .
C8 C 0.6201(5) -0.1125(3) 0.8898(2) 0.0648(11) Uani 1 1 d . . .
H8 H 0.5916 -0.1773 0.8640 0.078 Uiso 1 1 calc R B .
C9 C 0.5681(5) -0.0988(4) 0.9548(2) 0.0758(12) Uani 1 1 d . B .
H9 H 0.5042 -0.1540 0.9732 0.091 Uiso 1 1 calc R . .
C10 C 0.6117(4) -0.0025(3) 0.99202(19) 0.0599(10) Uani 1 1 d . . .
H10 H 0.5769 0.0100 1.0358 0.072 Uiso 1 1 calc R B .
C11 C 0.7094(3) 0.0752(3) 0.96213(16) 0.0424(7) Uani 1 1 d . B .
C12 C 0.6897(3) 0.2514(3) 1.03645(14) 0.0398(7) Uani 1 1 d . B .
C13 C 0.7858(3) 0.3466(3) 1.06618(15) 0.0410(7) Uani 1 1 d . . .
H13 H 0.8688 0.3617 1.0359 0.049 Uiso 1 1 calc R . .
C14 C 0.8414(6) 0.3054(4) 1.13486(19) 0.0783(13) Uani 1 1 d . . .
H14A H 0.7824 0.2398 1.1508 0.094 Uiso 1 1 calc R . .
H14B H 0.9419 0.2786 1.1308 0.094 Uiso 1 1 calc R . .
C15 C 0.8336(7) 0.3985(5) 1.1809(2) 0.104(2) Uani 1 1 d . . .
H15A H 0.9301 0.4321 1.1877 0.124 Uiso 1 1 calc R . .
H15B H 0.7980 0.3700 1.2243 0.124 Uiso 1 1 calc R . .
C16 C 0.7312(4) 0.4912(3) 1.15352(16) 0.0536(9) Uani 1 1 d . . .
H16A H 0.6387 0.4903 1.1776 0.064 Uiso 1 1 calc R . .
H16B H 0.7741 0.5693 1.1573 0.064 Uiso 1 1 calc R . .
C17 C 0.6371(4) 0.5324(3) 1.04040(17) 0.0490(8) Uani 1 1 d . . .
C18 C 0.6186(3) 0.5052(3) 0.96619(16) 0.0428(8) Uani 1 1 d . . .
C19 C 0.5124(4) 0.5638(3) 0.92979(18) 0.0516(9) Uani 1 1 d . . .
H19 H 0.4535 0.6199 0.9508 0.062 Uiso 1 1 calc R . .
C20 C 0.4944(4) 0.5387(3) 0.86225(18) 0.0568(9) Uani 1 1 d . . .
H20 H 0.4243 0.5787 0.8369 0.068 Uiso 1 1 calc R . .
C21 C 0.5804(4) 0.4542(3) 0.83220(16) 0.0483(8) Uani 1 1 d . . .
H21 H 0.5673 0.4332 0.7870 0.058 Uiso 1 1 calc R . .
C22 C 0.6879(3) 0.4010(3) 0.87170(15) 0.0396(7) Uani 1 1 d . . .
N1 N 0.7870(3) 0.3175(2) 0.84612(13) 0.0452(7) Uani 1 1 d . . .
H1 H 0.8729 0.3171 0.8639 0.054 Uiso 1 1 calc R . .
N2 N 0.8473(3) 0.0385(3) 0.75926(13) 0.0508(7) Uani 1 1 d . B .
N3 N 0.7603(3) 0.0633(2) 0.89986(13) 0.0406(6) Uani 1 1 d . . .
N4 N 0.7657(3) 0.1740(2) 0.99716(12) 0.0412(6) Uani 1 1 d . . .
H4 H 0.8581 0.1867 0.9932 0.049 Uiso 1 1 calc R B .
N5 N 0.7110(3) 0.4580(2) 1.08176(12) 0.0429(6) Uani 1 1 d . . .
N6 N 0.7075(3) 0.4257(2) 0.93737(12) 0.0432(6) Uani 1 1 d . . .
O1 O 0.6490(3) 0.2330(2) 0.76298(13) 0.0665(7) Uani 1 1 d . . .
O2 O 0.7271(3) -0.1338(2) 0.76076(13) 0.0686(7) Uani 1 1 d . B .
O3 O 0.5597(2) 0.2394(2) 1.04985(11) 0.0527(6) Uani 1 1 d . . .
O4 O 0.5817(4) 0.6226(2) 1.06330(14) 0.0764(9) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 123.4(3) y
O1 C1 C2 123.2(3) y
N1 C1 C2 113.2(3) y
N2 C2 C1 112.4(3) y
N2 C2 C3 103.0(3) y
C1 C2 C3 109.6(3) y
C4B C3 C2 105.5(5) y
C4A C3 C2 108.4(5) y
C3 C4A C5 102.6(6) y
C3 C4B C5 107.7(7) y
N2 C5 C4B 100.9(4) y
N2 C5 C4A 104.6(4) y
O2 C6 N2 120.1(3) y
O2 C6 C7 117.5(3) y
N2 C6 C7 122.4(3) y
N3 C7 C8 121.4(3) y
N3 C7 C6 119.9(3) y
C8 C7 C6 118.7(3) y
C9 C8 C7 119.7(3) y
C10 C9 C8 119.2(4) y
C9 C10 C11 117.6(3) y
N3 C11 C10 123.9(3) y
N3 C11 N4 114.0(3) y
C10 C11 N4 122.0(3) y
O3 C12 N4 123.2(3) y
O3 C12 C13 124.0(3) y
N4 C12 C13 112.6(3) y
N5 C13 C12 115.1(2) y
N5 C13 C14 103.5(3) y
C12 C13 C14 108.7(3) y
C15 C14 C13 109.3(3) y
C14 C15 C16 109.0(3) y
N5 C16 C15 104.1(3) y
O4 C17 N5 120.2(3) y
O4 C17 C18 118.8(3) y
N5 C17 C18 121.0(3) y
N6 C18 C19 122.0(3) y
N6 C18 C17 118.8(3) y
C19 C18 C17 119.1(3) y
C20 C19 C18 119.3(3) y
C19 C20 C21 119.7(3) y
C20 C21 C22 117.7(3) y
N6 C22 C21 123.1(3) y
N6 C22 N1 113.7(3) y
C21 C22 N1 123.1(3) y
C1 N1 C22 126.9(3) y
C6 N2 C5 118.3(3) y
C6 N2 C2 130.0(3) y
C5 N2 C2 111.5(3) y
C11 N3 C7 118.1(3) y
C12 N4 C11 127.1(3) y
C17 N5 C13 129.9(2) y
C17 N5 C16 118.8(3) y
C13 N5 C16 111.2(3) y
C22 N6 C18 118.1(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.213(4) y
C1 N1 1.374(4) y
C1 C2 1.511(5) y
C2 N2 1.475(4) y
C2 C3 1.526(5) y
C3 C4B 1.408(10) y
C3 C4A 1.491(10) y
C4A C5 1.533(10) y
C4B C5 1.514(10) y
C5 N2 1.467(5) y
C6 O2 1.230(4) y
C6 N2 1.353(4) y
C6 C7 1.501(5) y
C7 N3 1.346(4) y
C7 C8 1.379(5) y
C8 C9 1.374(6) y
C9 C10 1.374(5) y
C10 C11 1.385(5) y
C11 N3 1.319(4) y
C11 N4 1.413(4) y
C12 O3 1.225(4) y
C12 N4 1.360(4) y
C12 C13 1.509(4) y
C13 N5 1.467(4) y
C13 C14 1.520(5) y
C14 C15 1.393(6) y
C15 C16 1.507(6) y
C16 N5 1.476(4) y
C17 O4 1.227(4) y
C17 N5 1.353(4) y
C17 C18 1.505(5) y
C18 N6 1.339(4) y
C18 C19 1.378(5) y
C19 C20 1.371(5) y
C20 C21 1.373(5) y
C21 C22 1.390(5) y
C22 N6 1.337(4) y
C22 N1 1.403(4) y
