4R- and 4S-iodophenyl hydroxyproline, 4R-pentynoyl hydroxyproline, and S-propargyl-4-thiolphenylalanine: conformationally biased and tunable amino acids for bioorthogonal reactions.
Forbes, Christina R.; Pandey, Anil K.; Ganguly, Himal K.; Yap, Glenn P. A.; Zondlo, Neal J.; Organic & biomolecular chemistry 14 (2016) 2327–2346; doi:10.1039/c5ob02473k

data_7154923
_publ_section_title
;
 4R- and 4S-iodophenyl hydroxyproline, 4R-pentynoyl hydroxyproline, and
 S-propargyl-4-thiolphenylalanine: conformationally biased and tunable
 amino acids for bioorthogonal reactions.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2327
_journal_page_last               2346
_journal_paper_doi               10.1039/c5ob02473k
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H22 I N O5'
_chemical_formula_weight         447.25
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-11-20 deposited with the CCDC.
2016-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.961(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5131(13)
_cell_length_b                   16.581(3)
_cell_length_c                   8.9446(18)
_cell_measurement_reflns_used    3392
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.29
_cell_measurement_theta_min      2.29
_cell_volume                     960.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15874
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.677
_diffrn_reflns_theta_min         2.289
_exptl_absorpt_coefficient_mu    1.691
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.856
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 1630 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.031(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0356P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0765
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4168
_reflns_number_total             4955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02473k2.cif
_cod_data_source_block           neal030
_cod_depositor_comments
'Adding full bibliography for 7154921--7154923.cif.'
_cod_database_code               7154923
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.662
_shelx_estimated_absorpt_t_max   0.831
_shelx_res_checksum              88008