Formation of a cyclic tetrapeptide mimic by thermal azide–alkyne 1,3-dipolar cycloaddition
Krause, Martin R.; Goddard, Richard; Kubik, Stefan; Chemical Communications 46 (2010) 5307–5309; doi:10.1039/c0cc01154a

data_7111764
_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 \f- and \w-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/[\s^2^(Fo^2^)+(0.0619P)^2^+0.7217P] where P=(Fo^2^+2Fc^2^)/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>2\s(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