Mechanistic investigation of aziridine aldehyde-driven peptide macrocyclization: the imidoanhydride pathway
Zaretsky, Serge; Hickey, Jennifer L.; Tan, Joanne; Pichugin, Dmitry; St. Denis, Megan A.; Ler, Spencer; Chung, Benjamin K. W.; Scully, Conor C. G.; Yudin, Andrei K.; Chem. Sci. 6 (2015) 5446–; doi:10.1039/C5SC01958C

data_1521277
_publ_section_title
;
 Mechanistic investigation of aziridine aldehyde-driven peptide
 macrocyclization: the imidoanhydride pathway
;
_journal_issue                   10
_journal_name_full               'Chem. Sci.'
_journal_page_first              5446
_journal_paper_doi               10.1039/C5SC01958C
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H27 Br N4 O'
_chemical_formula_sum            'C20 H27 Br N4 O'
_chemical_formula_weight         419.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-06-01 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.310(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9698(4)
_cell_length_b                   18.4284(8)
_cell_length_c                   12.3981(5)
_cell_measurement_reflns_used    9115
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      67.01
_cell_measurement_theta_min      4.33
_cell_volume                     2027.88(15)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            39585
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.191
_diffrn_reflns_theta_min         3.603
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    2.882
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       Block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
; 
 Flack x determined using 3350 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.016(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7137
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.4954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0590
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                7079
_reflns_number_total             7137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc01958c2.cif
_cod_data_source_block           d14137
_cod_depositor_comments
'Adding full bibliography for 1521277--1521278.cif.'
_cod_database_code               1521277
_shelx_estimated_absorpt_t_min   0.570
_shelx_estimated_absorpt_t_max   0.625
_shelxl_version_number           2014/6
_shelx_res_checksum              2732
_shelx_hkl_checksum              17542