#------------------------------------------------------------------------------
#$Date: 2021-07-31 04:52:40 +0300 (Sat, 31 Jul 2021) $
#$Revision: 267842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564279.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1564279
loop_
_publ_author_name
'Eagling, Louise'
'Leonard, Daniel J.'
'Schwarz, Maria'
'Urruzuno, Iñaki'
'Boden, Grace'
'Wailes, J. Steven'
'Ward, John W.'
'Clayden, Jonathan'
_publ_section_title
;
 ‘Reverse biomimetic’ 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_absolute_configuration syn
_chemical_formula_moiety         'C17 H24 N2 O3'
_chemical_formula_sum            'C17 H24 N2 O3'
_chemical_formula_weight         304.38
_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   geom
_audit_creation_date             2018-06-07
_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                 95.471(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7444(2)
_cell_length_b                   12.0901(5)
_cell_length_c                   12.1546(6)
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.38
_cell_volume                     840.30(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6822
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.082
_diffrn_reflns_theta_min         2.381
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0549 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.8376. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0417
_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/[σ²(Fo²)+(0.0369P)²+0.2057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.579
_reflns_Friedel_fraction_full    0.684
_reflns_Friedel_fraction_max     0.638
_reflns_number_gt                2596
_reflns_number_total             3061
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc03554a2.cif
_cod_data_source_block           le166_4
_cod_database_code               1564279
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0010(4) 0.24117(17) 0.07517(18) 0.0271(5) Uani 1 1 d . . . . .
O2 O 0.2960(4) 0.88248(16) 0.05586(19) 0.0284(5) Uani 1 1 d . . . . .
H2 H 0.208777 0.843457 0.012086 0.043 Uiso 1 1 calc GR . . . .
O3 O 0.6629(3) 0.50155(16) 0.30498(16) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.2800(4) 0.23045(19) 0.2218(2) 0.0201(5) Uani 1 1 d . . . . .
N2 N 0.3124(4) 0.41010(18) 0.27270(18) 0.0156(5) Uani 1 1 d . . . . .
C1 C 0.3868(5) 0.2998(2) 0.3126(2) 0.0166(6) Uani 1 1 d . . . . .
H1 H 0.560956 0.294291 0.315307 0.020 Uiso 1 1 calc R . . . .
C2 C 0.1214(5) 0.2837(2) 0.1526(2) 0.0199(6) Uani 1 1 d . . . . .
C3 C 0.1216(5) 0.4041(2) 0.1837(2) 0.0164(6) Uani 1 1 d . . . . .
H3 H -0.030967 0.426736 0.210128 0.020 Uiso 1 1 calc R . . . .
C4 C 0.1982(5) 0.4850(2) 0.0964(2) 0.0185(6) Uani 1 1 d . . . . .
H4A H 0.061451 0.521351 0.055769 0.022 Uiso 1 1 calc R . . . .
H4B H 0.290162 0.446790 0.043014 0.022 Uiso 1 1 calc R . . . .
C5 C 0.3512(5) 0.5702(2) 0.1668(2) 0.0168(6) Uani 1 1 d . . . . .
C6 C 0.5345(5) 0.6235(2) 0.1051(2) 0.0202(6) Uani 1 1 d . . . . .
H6 H 0.637796 0.577222 0.069401 0.024 Uiso 1 1 calc R . . . .
C7 C 0.5596(5) 0.7315(2) 0.0978(2) 0.0213(6) Uani 1 1 d . . . . .
H7 H 0.686663 0.758434 0.060869 0.026 Uiso 1 1 calc R . . . .
C8 C 0.4024(5) 0.8144(2) 0.1434(3) 0.0202(6) Uani 1 1 d . . . . .
H8 H 0.501431 0.863311 0.195045 0.024 Uiso 1 1 calc R . . . .
C9 C 0.2189(5) 0.7624(2) 0.2080(2) 0.0180(6) Uani 1 1 d . . . . .
C10 C 0.1988(5) 0.6533(2) 0.2183(2) 0.0178(6) Uani 1 1 d . . . . .
H10 H 0.080807 0.626088 0.260860 0.021 Uiso 1 1 calc R . . . .
C11 C 0.0546(5) 0.8402(3) 0.2572(3) 0.0260(7) Uani 1 1 d . . . . .
H11A H -0.017582 0.889217 0.199412 0.039 Uiso 1 1 calc GR . . . .
H11B H 0.141268 0.884614 0.314874 0.039 Uiso 1 1 calc GR . . . .
H11C H -0.067353 0.797851 0.289516 0.039 Uiso 1 1 calc GR . . . .
C12 C 0.4669(4) 0.4928(2) 0.2567(2) 0.0155(5) Uani 1 1 d . . . . .
C13 C 0.3095(5) 0.2742(2) 0.4276(3) 0.0205(6) Uani 1 1 d . . . . .
C14 C 0.0427(5) 0.2731(3) 0.4249(3) 0.0264(7) Uani 1 1 d . . . . .
H14A H -0.021142 0.215526 0.373818 0.040 Uiso 1 1 calc GR . . . .
H14B H -0.019401 0.345273 0.399948 0.040 Uiso 1 1 calc GR . . . .
H14C H -0.002282 0.257728 0.499146 0.040 Uiso 1 1 calc GR . . . .
C15 C 0.4079(5) 0.1619(3) 0.4692(3) 0.0309(8) Uani 1 1 d . . . . .
H15A H 0.575827 0.158886 0.460997 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.328012 0.102320 0.425803 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.382431 0.152772 0.547258 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.4103(5) 0.3647(3) 0.5061(3) 0.0284(7) Uani 1 1 d . . . . .
H16A H 0.338918 0.435887 0.483912 0.043 Uiso 1 1 calc GR . . . .
H16B H 0.579871 0.369075 0.503067 0.043 Uiso 1 1 calc GR . . . .
H16C H 0.376518 0.347163 0.581700 0.043 Uiso 1 1 calc GR . . . .
C17 C 0.3510(7) 0.1168(3) 0.2026(3) 0.0387(9) Uani 1 1 d . . . . .
H17A H 0.278730 0.067224 0.253402 0.058 Uiso 1 1 calc GR . . . .
H17B H 0.521595 0.110908 0.215430 0.058 Uiso 1 1 calc GR . . . .
H17C H 0.300402 0.095771 0.126217 0.058 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 109.5 . . ?
C2 N1 C1 113.9(2) . . ?
C2 N1 C17 122.3(3) . . ?
C17 N1 C1 123.6(3) . . ?
C3 N2 C1 111.9(2) . . ?
C12 N2 C1 122.7(2) . . ?
C12 N2 C3 112.5(2) . . ?
N1 C1 H1 109.3 . . ?
N1 C1 C13 115.5(2) . . ?
N2 C1 N1 100.5(2) . . ?
N2 C1 H1 109.3 . . ?
N2 C1 C13 112.5(2) . . ?
C13 C1 H1 109.3 . . ?
O1 C2 N1 125.6(3) . . ?
O1 C2 C3 125.6(3) . . ?
N1 C2 C3 108.8(2) . . ?
N2 C3 C2 102.4(2) . . ?
N2 C3 H3 111.4 . . ?
N2 C3 C4 103.6(2) . . ?
C2 C3 H3 111.4 . . ?
C2 C3 C4 115.9(2) . . ?
C4 C3 H3 111.4 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
C3 C4 C5 103.0(2) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C6 C5 C4 113.4(2) . . ?
C6 C5 C10 112.6(2) . . ?
C6 C5 C12 109.9(2) . . ?
C10 C5 C4 110.5(2) . . ?
C10 C5 C12 109.8(2) . . ?
C12 C5 C4 99.9(2) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 C5 123.2(3) . . ?
C7 C6 H6 118.4 . . ?
C6 C7 H7 117.7 . . ?
C6 C7 C8 124.5(3) . . ?
C8 C7 H7 117.7 . . ?
O2 C8 C7 109.9(2) . . ?
O2 C8 H8 107.6 . . ?
O2 C8 C9 110.8(2) . . ?
C7 C8 H8 107.6 . . ?
C7 C8 C9 113.0(2) . . ?
C9 C8 H8 107.6 . . ?
C10 C9 C8 122.2(2) . . ?
C10 C9 C11 121.5(3) . . ?
C11 C9 C8 116.4(2) . . ?
C5 C10 H10 117.9 . . ?
C9 C10 C5 124.3(3) . . ?
C9 C10 H10 117.9 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N2 125.3(3) . . ?
O3 C12 C5 127.1(3) . . ?
N2 C12 C5 107.7(2) . . ?
C14 C13 C1 110.9(2) . . ?
C14 C13 C15 109.6(2) . . ?
C15 C13 C1 110.4(2) . . ?
C16 C13 C1 107.3(2) . . ?
C16 C13 C14 109.8(3) . . ?
C16 C13 C15 108.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.232(3) . ?
O2 H2 0.8400 . ?
O2 C8 1.435(3) . ?
O3 C12 1.224(3) . ?
N1 C1 1.472(4) . ?
N1 C2 1.344(4) . ?
N1 C17 1.459(4) . ?
N2 C1 1.468(3) . ?
N2 C3 1.467(3) . ?
N2 C12 1.363(3) . ?
C1 H1 1.0000 . ?
C1 C13 1.538(4) . ?
C2 C3 1.504(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.537(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.556(4) . ?
C5 C6 1.496(4) . ?
C5 C10 1.507(4) . ?
C5 C12 1.540(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.318(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.490(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.510(4) . ?
C9 C10 1.331(4) . ?
C9 C11 1.497(4) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.530(4) . ?
C13 C15 1.537(4) . ?
C13 C16 1.529(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 N2 -174.7(3) . . . . ?
O1 C2 C3 C4 -62.7(4) . . . . ?
O2 C8 C9 C10 121.6(3) . . . . ?
O2 C8 C9 C11 -56.5(3) . . . . ?
N1 C1 C13 C14 -51.9(3) . . . . ?
N1 C1 C13 C15 69.8(3) . . . . ?
N1 C1 C13 C16 -171.9(2) . . . . ?
N1 C2 C3 N2 4.1(3) . . . . ?
N1 C2 C3 C4 116.1(2) . . . . ?
N2 C1 C13 C14 62.7(3) . . . . ?
N2 C1 C13 C15 -175.6(2) . . . . ?
N2 C1 C13 C16 -57.2(3) . . . . ?
N2 C3 C4 C5 -28.2(3) . . . . ?
C1 N1 C2 O1 -175.1(3) . . . . ?
C1 N1 C2 C3 6.1(3) . . . . ?
C1 N2 C3 C2 -12.9(3) . . . . ?
C1 N2 C3 C4 -133.8(2) . . . . ?
C1 N2 C12 O3 -26.1(4) . . . . ?
C1 N2 C12 C5 153.0(2) . . . . ?
C2 N1 C1 N2 -13.4(3) . . . . ?
C2 N1 C1 C13 107.9(3) . . . . ?
C2 C3 C4 C5 -139.5(2) . . . . ?
C3 N2 C1 N1 15.9(3) . . . . ?
C3 N2 C1 C13 -107.5(2) . . . . ?
C3 N2 C12 O3 -164.2(2) . . . . ?
C3 N2 C12 C5 14.9(3) . . . . ?
C3 C4 C5 C6 152.3(2) . . . . ?
C3 C4 C5 C10 -80.1(3) . . . . ?
C3 C4 C5 C12 35.5(2) . . . . ?
C4 C5 C6 C7 126.9(3) . . . . ?
C4 C5 C10 C9 -126.1(3) . . . . ?
C4 C5 C12 O3 147.6(3) . . . . ?
C4 C5 C12 N2 -31.5(3) . . . . ?
C5 C6 C7 C8 -3.9(5) . . . . ?
C6 C5 C10 C9 1.8(4) . . . . ?
C6 C5 C12 O3 28.1(4) . . . . ?
C6 C5 C12 N2 -151.0(2) . . . . ?
C6 C7 C8 O2 -119.7(3) . . . . ?
C6 C7 C8 C9 4.6(4) . . . . ?
C7 C8 C9 C10 -2.3(4) . . . . ?
C7 C8 C9 C11 179.6(3) . . . . ?
C8 C9 C10 C5 -0.8(5) . . . . ?
C10 C5 C6 C7 0.5(4) . . . . ?
C10 C5 C12 O3 -96.3(3) . . . . ?
C10 C5 C12 N2 84.6(3) . . . . ?
C11 C9 C10 C5 177.2(3) . . . . ?
C12 N2 C1 N1 -122.4(3) . . . . ?
C12 N2 C1 C13 114.2(3) . . . . ?
C12 N2 C3 C2 129.7(2) . . . . ?
C12 N2 C3 C4 8.9(3) . . . . ?
C12 C5 C6 C7 -122.3(3) . . . . ?
C12 C5 C10 C9 124.7(3) . . . . ?
C17 N1 C1 N2 162.0(3) . . . . ?
C17 N1 C1 C13 -76.7(3) . . . . ?
C17 N1 C2 O1 9.4(4) . . . . ?
C17 N1 C2 C3 -169.4(3) . . . . ?
