‘Reverse biomimetic’ synthesis of l-arogenate and its stabilized analogues from l-tyrosine
Eagling, Louise; Leonard, Daniel J.; Schwarz, Maria; Urruzuno, Iñaki; Boden, Grace; Wailes, J. Steven; Ward, John W.; Clayden, Jonathan; Chemical Science  (2021) –; doi:10.1039/D1SC03554A

data_1564280
_publ_section_title
;
 &#x2018;Reverse biomimetic&#x2019; synthesis of l-arogenate and its
 stabilized analogues from l-tyrosine
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03554A
_journal_year                    2021
_chemical_formula_moiety         'C16 H26 N2 O3'
_chemical_formula_sum            'C16 H26 N2 O3'
_chemical_formula_weight         294.39
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-12 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.9895(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.94680(10)
_cell_length_b                   13.2423(3)
_cell_length_c                   10.0750(3)
_cell_measurement_reflns_used    8311
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.56
_cell_volume                     785.70(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      99.97
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18866
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.966
_diffrn_reflns_theta_min         2.041
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0630 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.8471. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3773
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0510P)^2^+0.0717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3588
_reflns_number_total             3773
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03554a2.cif
_cod_data_source_block           le172_f23_27
_cod_database_code               1564280
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
;
_shelx_res_checksum              52983
_olex2_exptl_crystal_mounting_method 'Oil on glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'