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_1521278
_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         'C33 H51 N7 O6, H2 O'
_chemical_formula_sum            'C33 H53 N7 O7'
_chemical_formula_weight         659.82
_chemical_name_systematic
;
 ?
;
_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-2013
_audit_update_record
;
2015-06-01 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2990(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0804(3)
_cell_length_b                   9.9982(3)
_cell_length_c                   19.7575(6)
_cell_measurement_reflns_used    9091
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      65.61
_cell_measurement_theta_min      4.51
_cell_volume                     1937.88(10)
_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 0.967
_diffrn_measured_fraction_theta_max 0.982
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_laue_measured_fraction_full 0.967
_diffrn_reflns_laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            36769
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.745
_diffrn_reflns_theta_min         2.298
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.7079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_platon_squeeze_details
;
During the
refinement of the structure, electron density peaks were located
that were believed to be highly disordered
solvent molecules (possibly DMSO/EtOH). Attempts
made to model the solvent molecule were not successful.
The SQUEEZE option in PLATON (Spek, 2003) indicated there was a
large solvent cavity 223 A3. In the final cycles of refinement,
this contribution 74e's to the
electron density was removed from the observed data. The
density, the F(000) value, the molecular weight and the formula are
given without taking into account the results obtained with the
SQUEEZE option PLATON (Spek, 2003). Similar treatments of disordered
solvent molecules were carried out by St\"ahler et al. (2001),
Cox et al. (2003), Mohamed et al. (2003) and Athimoolam et al. (2005).
References:

Spek, A. L. (2009). <i>Acta Cryst.</i> <b>D65</b>, 148--155.

Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R.K. (2005).
Acta Cryst. E61, m2014-m2017.

Cox, J.P., Kumarasammy, Y., Nahar, L., Sarkar D.S. & Shoeb, M.
(2003). Acta Cryst. E59, o975-o977.

Mohamed, A.A., Krause Bauer, A.J., Bruce, E.A. & Bruce M.R.M.
(2003). Acta Cryst. C59, m84-m86.

St\"ahler, R., N\"ather, C. & Bensch, W. (2001). Acta Cryst.
C57, 26-27.
;
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6593
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0522P)^2^+0.6512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1089
_reflns_Friedel_coverage         0.842
_reflns_friedel_fraction_full    0.923
_reflns_friedel_fraction_max     0.938
_reflns_number_gt                6365
_reflns_number_total             6593
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc01958c2.cif
_cod_data_source_block           d13160_sq_d
_cod_depositor_comments
'Adding full bibliography for 1521277--1521278.cif.'
_cod_database_code               1521278
_shelx_estimated_absorpt_t_min   0.937
_shelx_estimated_absorpt_t_max   0.968
_shelxl_version_number           2013-3