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_7111763
_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 rmad
_chemical_compound_source        dimethylsulfoxide/water
_chemical_formula_moiety         'C20 H18 N10 O2, 2(C2 H6 O S)'
_chemical_formula_sum            'C24 H30 N10 O4 S2'
_chemical_formula_weight         586.70
_chemical_name_common
;
cyclo-bis-((R)ethyl-1,5-triazol-2,6-pyridyl-amino-carbonyl)
di(dimethylsulfoxide) solute
;
_chemical_name_systematic
;
cyclo-bis-((R)ethyl-1,5-triazol-2,6-pyridyl-amino-carbonyl)
di(dimethylsulfoxide) solute
;
_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_block_code                mk-369-Probe-1
_audit_creation_date             2010-02-18
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2734(12)
_cell_length_b                   12.7812(13)
_cell_length_c                   8.6196(9)
_cell_measurement_reflns_used    9387
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.9860
_cell_measurement_theta_min      2.3006
_cell_volume                     1352.1(2)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'APEX2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.06
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            89526
_diffrn_reflns_theta_full        35.00
_diffrn_reflns_theta_max         36.50
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.99527
_exptl_absorpt_correction_T_min  0.99192
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         6518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0751
_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^)+(0.0054P)^2^+3.2988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.1819
_reflns_number_gt                6260
_reflns_number_total             6518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC01154Asup1.cif
_cod_data_source_block           9.2DMSO
_cod_original_sg_symbol_Hall     'p 2 2ab'
_cod_database_code               7111763