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#$Date: 2024-07-05 20:41:13 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293207 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/31/7063125.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_7063125
loop_
_publ_author_name
'Bakija, Marija'
'Perić, Berislav'
'Kirin, Srećko I.'
_publ_section_title
;
 Oxazoline amino acid bioconjugates: one-pot synthesis and analysis of
 supramolecular interactions
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8702
_journal_page_last               8719
_journal_paper_doi               10.1039/D4NJ00995A
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H22 N2 O4'
_chemical_formula_sum            'C20 H22 N2 O4'
_chemical_formula_weight         354.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.082(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.688(4)
_cell_length_b                   5.2784(6)
_cell_length_c                   16.099(2)
_cell_measurement_reflns_used    598
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.1640
_cell_measurement_theta_min      4.1410
_cell_volume                     1861.5(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997), Mercury (C. F. Macrae et al., 2020)
;
_computing_publication_material
;
'SHELXL-2018/3 (Sheldrick, 2018), CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4323
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2235
_diffrn_reflns_point_group_measured_fraction_full 0.792
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_theta_full        51.376
_diffrn_reflns_theta_max         51.376
_diffrn_reflns_theta_min         2.843
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         1615
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0549
_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)+(0.0641P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.399
_reflns_Friedel_fraction_full    0.527
_reflns_Friedel_fraction_max     0.526
_reflns_number_gt                1209
_reflns_number_total             1615
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00995a6.cif
_cod_data_source_block           1n4
_cod_depositor_comments
'Adding full bibliography for 7063124--7063134.cif.'
_cod_original_cell_volume        1861.6(5)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7063125
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
C1 C 0.0826(3) 0.6777(16) 0.5322(5) 0.064(2) Uani 1 1 d . . . . .
H1 H 0.057899 0.820908 0.524361 0.077 Uiso 1 1 calc R U . . .
C2 C 0.0854(3) 0.5274(16) 0.6011(5) 0.064(2) Uani 1 1 d . . . . .
C3 C 0.1233(3) 0.3085(16) 0.6132(5) 0.067(2) Uani 1 1 d . . . . .
H3 H 0.124521 0.201838 0.659604 0.081 Uiso 1 1 calc R U . . .
C4 C 0.1576(3) 0.2534(17) 0.5579(5) 0.073(2) Uani 1 1 d . . . . .
H4 H 0.183368 0.113220 0.568149 0.088 Uiso 1 1 calc R U . . .
C4A C 0.1547(3) 0.4061(16) 0.4855(5) 0.062(2) Uani 1 1 d . . . . .
C5 C 0.1888(3) 0.3502(16) 0.4248(5) 0.067(2) Uani 1 1 d . . . . .
H5 H 0.215519 0.213161 0.434558 0.080 Uiso 1 1 calc R U . . .
C6 C 0.1831(3) 0.4939(17) 0.3528(5) 0.061(2) Uani 1 1 d . . . . .
C7 C 0.1447(3) 0.7100(16) 0.3399(5) 0.069(2) Uani 1 1 d . . . . .
H7 H 0.141575 0.811924 0.291831 0.083 Uiso 1 1 calc R U . . .
C8 C 0.1126(3) 0.7684(16) 0.3974(5) 0.068(2) Uani 1 1 d . . . . .
H8 H 0.087183 0.909661 0.387137 0.081 Uiso 1 1 calc R U . . .
C8A C 0.1160(3) 0.6237(16) 0.4720(5) 0.064(2) Uani 1 1 d . . . . .
O1O O 0.2560(3) 0.2322(12) 0.3113(3) 0.0887(18) Uani 1 1 d . . . . .
C2O C 0.2137(4) 0.4179(17) 0.2875(6) 0.070(3) Uani 1 1 d . . . . .
N3O N 0.2034(3) 0.5009(14) 0.2123(5) 0.078(2) Uani 1 1 d . . . . .
C4O C 0.2394(4) 0.3478(18) 0.1661(5) 0.075(2) Uani 1 1 d . . . . .
C5O C 0.2795(4) 0.193(2) 0.2380(5) 0.092(3) Uani 1 1 d . . . . .
H5OA H 0.277681 0.014915 0.222562 0.111 Uiso 1 1 calc R U . . .
H5OB H 0.321573 0.249134 0.249840 0.111 Uiso 1 1 calc R U . . .
C6O C 0.2770(5) 0.511(2) 0.1216(7) 0.130(4) Uani 1 1 d . . . . .
H6OA H 0.301133 0.403807 0.095012 0.195 Uiso 1 1 calc R U . . .
H6OB H 0.303492 0.618365 0.163130 0.195 Uiso 1 1 calc R U . . .
H6OC H 0.250339 0.612923 0.078464 0.195 Uiso 1 1 calc R U . . .
C7O C 0.1964(4) 0.181(2) 0.1023(6) 0.127(4) Uani 1 1 d . . . . .
H7OB H 0.168564 0.284666 0.060912 0.190 Uiso 1 1 calc R U . . .
H7OC H 0.173793 0.076329 0.131862 0.190 Uiso 1 1 calc R U . . .
H7OA H 0.219247 0.075839 0.073319 0.190 Uiso 1 1 calc R U . . .
CC C 0.0520(3) 0.5997(19) 0.6657(5) 0.067(2) Uani 1 1 d . . . . .
OC O 0.0429(3) 0.8244(11) 0.6798(4) 0.0807(18) Uani 1 1 d . . . . .
NA N 0.0314(4) 0.4126(17) 0.7077(5) 0.079(3) Uani 1 1 d . . . . .
HA H 0.047(4) 0.285(18) 0.703(5) 0.08(4) Uiso 1 1 d . . . . .
C1A C 0.0075(4) 0.4697(16) 0.7805(5) 0.069(2) Uani 1 1 d . . . . .
H1A H -0.020200 0.614562 0.765399 0.083 Uiso 1 1 calc R U . . .
C2A C 0.0574(4) 0.5389(18) 0.8576(6) 0.080(3) Uani 1 1 d . . . . .
C3A C -0.0289(4) 0.2432(18) 0.7999(6) 0.099(3) Uani 1 1 d . . . . .
H3AC H -0.059188 0.195587 0.748636 0.149 Uiso 1 1 calc R U . . .
H3AA H -0.048471 0.288796 0.843864 0.149 Uiso 1 1 calc R U . . .
H3AB H -0.001750 0.103279 0.819272 0.149 Uiso 1 1 calc R U . . .
O1A O 0.1103(3) 0.4963(17) 0.8687(4) 0.121(3) Uani 1 1 d . . . . .
O2A O 0.0362(2) 0.6739(14) 0.9137(4) 0.101(2) Uani 1 1 d . . . . .
CMA C 0.0799(4) 0.755(3) 0.9903(6) 0.128(5) Uani 1 1 d . . . . .
HMAC H 0.116910 0.659113 0.997426 0.192 Uiso 1 1 calc R U . . .
HMAA H 0.063735 0.727758 1.039083 0.192 Uiso 1 1 calc R U . . .
HMAB H 0.088478 0.931641 0.985867 0.192 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 C8A 121.8(7) . . ?
C1 C2 C3 119.2(7) . . ?
C1 C2 CC 120.0(8) . . ?
C3 C2 CC 120.8(7) . . ?
C4 C3 C2 120.9(7) . . ?
C3 C4 C4A 120.6(8) . . ?
C4 C4A C8A 118.9(7) . . ?
C4 C4A C5 122.2(8) . . ?
C8A C4A C5 118.9(7) . . ?
C6 C5 C4A 121.2(7) . . ?
C5 C6 C7 119.4(7) . . ?
C5 C6 C2O 120.1(8) . . ?
C7 C6 C2O 120.4(8) . . ?
C8 C7 C6 120.2(8) . . ?
C7 C8 C8A 122.6(8) . . ?
C1 C8A C8 123.8(8) . . ?
C1 C8A C4A 118.6(7) . . ?
C8 C8A C4A 117.5(7) . . ?
C2O O1O C5O 105.0(6) . . ?
N3O C2O O1O 117.9(7) . . ?
N3O C2O C6 126.6(9) . . ?
O1O C2O C6 115.5(8) . . ?
C2O N3O C4O 107.8(7) . . ?
N3O C4O C7O 108.5(7) . . ?
N3O C4O C5O 102.2(6) . . ?
C7O C4O C5O 111.2(8) . . ?
N3O C4O C6O 112.3(8) . . ?
C7O C4O C6O 110.7(8) . . ?
C5O C4O C6O 111.5(8) . . ?
O1O C5O C4O 105.9(7) . . ?
OC CC NA 121.0(8) . . ?
OC CC C2 121.0(8) . . ?
NA CC C2 118.0(8) . . ?
CC NA C1A 120.4(8) . . ?
NA C1A C2A 111.3(7) . . ?
NA C1A C3A 109.8(7) . . ?
C2A C1A C3A 110.7(7) . . ?
O1A C2A O2A 121.8(9) . . ?
O1A C2A C1A 126.6(8) . . ?
O2A C2A C1A 111.4(8) . . ?
C2A O2A CMA 116.8(7) . . ?
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
C1 C2 1.352(9) . ?
C1 C8A 1.406(9) . ?
C2 C3 1.422(10) . ?
C2 CC 1.487(10) . ?
C3 C4 1.359(9) . ?
C4 C4A 1.405(10) . ?
C4A C8A 1.426(10) . ?
C4A C5 1.427(9) . ?
C5 C6 1.363(10) . ?
C6 C7 1.417(10) . ?
C6 C2O 1.458(10) . ?
C7 C8 1.354(9) . ?
C8 C8A 1.409(9) . ?
O1O C2O 1.356(10) . ?
O1O C5O 1.431(8) . ?
C2O N3O 1.251(9) . ?
N3O C4O 1.480(9) . ?
C4O C7O 1.504(11) . ?
C4O C5O 1.512(11) . ?
C4O C6O 1.517(11) . ?
CC OC 1.235(9) . ?
CC NA 1.348(11) . ?
NA C1A 1.444(10) . ?
C1A C2A 1.492(11) . ?
C1A C3A 1.531(11) . ?
C2A O1A 1.188(9) . ?
C2A O2A 1.334(9) . ?
O2A CMA 1.432(10) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
NA HA OC 0.77(9) 2.46(9) 3.158(11) 152(8) 1_545 yes
