Substituent Effects on Energetics of Peptide-Carboxylate Hydrogen Bonds as Studied by 1H NMR Spectroscopy: Implications for Enzyme Catalysis
Bright U. Emenike; Albert Tianxiang Liu; Elsy P. Naveo; John D. Roberts; Journal of Organic Chemistry 78 (2013) 11765–11771; doi:10.1021/jo401762m

data_4028784
_publ_contact_author_address
;
Beckman Institute
Caltech 139-74
Pasadena CA 91125
USA
;
_publ_contact_author_email       xray@caltech.edu
_publ_section_title
;
 Substituent Effects on Energetics of Peptide-Carboxylate Hydrogen Bonds
 as Studied by 1H NMR Spectroscopy: Implications for Enzyme Catalysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11765
_journal_page_last               11771
_journal_paper_doi               10.1021/jo401762m
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H10 N2 O5'
_chemical_formula_sum            'C14 H10 N2 O5'
_chemical_formula_weight         286.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-21
_audit_creation_method
; 
  Olex2 1.2 
  (compiled May  9 2012 12:37:22, GUI svn.r4230) 
 SHELXL-2012,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 118.152(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.6966(11)
_cell_length_b                   4.8683(2)
_cell_length_c                   21.0108(9)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    100
_cell_measurement_theta_max      39.03
_cell_measurement_theta_min      2.20
_cell_volume                     2497.85(18)
_computing_cell_refinement       'SAINT V8.27B (Bruker-AXS, 2007)'
_computing_data_collection       'SMART v5.054 (Bruker-AXS, 2001)'
_computing_data_reduction        'SAINT V8.27B (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
 and SHELXTL (Bruker-AXS, 2007)
;
_computing_structure_refinement  'SHELXL-2012/5 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART 1000 ccd'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            60562
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         41.077
_diffrn_reflns_theta_min         1.668
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS v2012/1 (Bruker-AXS, 2001) was used for absorption correction. 
wR2(int) was 0.0570 before and 0.0502 after correction. 
The Ratio of minimum to maximum transmission is 0.9295. 
The \l/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.235
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.508
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         8041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.508
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)] 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5863
_reflns_number_total             8041
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo401762m_si_001.cif
_cod_data_source_block           bue001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_source_target' value 'MO' changed to 'Mo' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               4028784
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.961
_shelx_res_checksum              87032
_shelxl_version_number           2012-5