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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/7/06/31/7063126.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_7063126
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         'C33 H36 N4 O6, C H4 O'
_chemical_formula_sum            'C34 H40 N4 O7'
_chemical_formula_weight         616.70
_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     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                 91.905(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.85790(10)
_cell_length_b                   21.1948(4)
_cell_length_c                   15.9374(3)
_cell_measurement_reflns_used    4259
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7630
_cell_measurement_theta_min      3.4770
_cell_volume                     1640.04(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.984
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8050
_diffrn_reflns_point_group_measured_fraction_full 0.726
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.043
_diffrn_reflns_theta_min         3.471
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61407
_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    1.249
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         4801
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0504
_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)+(0.0736P)²+0.2653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.386
_reflns_Friedel_fraction_full    0.437
_reflns_Friedel_fraction_max     0.402
_reflns_number_gt                4108
_reflns_number_total             4801
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00995a6.cif
_cod_data_source_block           1m6
_cod_depositor_comments
'Adding full bibliography for 7063124--7063134.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7063126
_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+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 0.4666(9) 0.5381(2) 0.5787(3) 0.0557(10) Uani 1 1 d . . . . .
C2 C 0.6339(9) 0.4962(2) 0.5365(2) 0.0523(9) Uani 1 1 d . . . . .
H2 H 0.635495 0.453654 0.550492 0.063 Uiso 1 1 calc R U . . .
C3 C 0.8002(9) 0.5187(3) 0.4726(2) 0.0545(10) Uani 1 1 d . . . . .
C4 C 0.7960(12) 0.5821(3) 0.4514(3) 0.0730(14) Uani 1 1 d . . . . .
H4 H 0.904770 0.596783 0.408624 0.088 Uiso 1 1 calc R U . . .
C5 C 0.6323(14) 0.6231(3) 0.4933(4) 0.0830(16) Uani 1 1 d . . . . .
H5 H 0.629438 0.665578 0.478813 0.100 Uiso 1 1 calc R U . . .
C6 C 0.4694(12) 0.6013(3) 0.5578(4) 0.0735(13) Uani 1 1 d . . . . .
H6 H 0.361687 0.629578 0.586837 0.088 Uiso 1 1 calc R U . . .
O1O O 1.1173(8) 0.4973(2) 0.3644(2) 0.0773(11) Uani 1 1 d . . . . .
C2O C 0.9800(9) 0.4739(3) 0.4296(2) 0.0583(12) Uani 1 1 d . . . . .
N3O N 1.0175(10) 0.4165(2) 0.4477(2) 0.0682(11) Uani 1 1 d . . . . .
C4O C 1.2130(11) 0.3903(3) 0.3875(3) 0.0702(14) Uani 1 1 d . . . . .
H4O H 1.381171 0.377169 0.418398 0.084 Uiso 1 1 calc R U . . .
C5O C 1.2788(12) 0.4473(3) 0.3330(3) 0.0774(17) Uani 1 1 d . . . . .
H5OA H 1.473285 0.457526 0.337691 0.093 Uiso 1 1 calc R U . . .
H5OB H 1.229800 0.438966 0.274500 0.093 Uiso 1 1 calc R U . . .
C3B C 1.0907(10) 0.3340(3) 0.3420(3) 0.0652(13) Uani 1 1 d . . . . .
C4B C 1.1835(14) 0.2730(4) 0.3613(4) 0.0851(17) Uani 1 1 d . . . . .
H4B H 1.324271 0.267286 0.401511 0.102 Uiso 1 1 calc R U . . .
C5B C 1.0662(16) 0.2208(4) 0.3205(5) 0.0942(19) Uani 1 1 d . . . . .
H5B H 1.125751 0.180442 0.334925 0.113 Uiso 1 1 calc R U . . .
C6B C 0.8674(14) 0.2285(4) 0.2605(4) 0.0882(19) Uani 1 1 d . . . . .
H6B H 0.793266 0.193426 0.232894 0.106 Uiso 1 1 calc R U . . .
C7B C 0.7745(13) 0.2872(4) 0.2402(4) 0.0841(17) Uani 1 1 d . . . . .
H7B H 0.637826 0.292155 0.198421 0.101 Uiso 1 1 calc R U . . .
C8B C 0.8836(11) 0.3402(3) 0.2817(4) 0.0733(14) Uani 1 1 d . . . . .
H8B H 0.815221 0.380040 0.268307 0.088 Uiso 1 1 calc R U . . .
CC C 0.2845(9) 0.5171(3) 0.6477(3) 0.0607(12) Uani 1 1 d . . . . .
OC O 0.2060(11) 0.5551(3) 0.6997(3) 0.1027(16) Uani 1 1 d . . . . .
NG N 0.2098(8) 0.4570(2) 0.6473(2) 0.0606(10) Uani 1 1 d D . . . .
HG H 0.278(12) 0.431(3) 0.613(3) 0.078(18) Uiso 1 1 d D . . . .
C1G C 0.0331(9) 0.4321(3) 0.7108(3) 0.0659(13) Uani 1 1 d . . . . .
H1GB H -0.063065 0.395284 0.688642 0.079 Uiso 1 1 calc R U . . .
H1GA H -0.103923 0.463554 0.724014 0.079 Uiso 1 1 calc R U . . .
C2G C 0.1918(8) 0.4139(2) 0.7905(3) 0.0528(10) Uani 1 1 d . . . . .
O1G O 0.4438(6) 0.4139(3) 0.7960(2) 0.0818(13) Uani 1 1 d . . . . .
NV N 0.0313(6) 0.39835(18) 0.85398(19) 0.0479(8) Uani 1 1 d D . . . .
HV H -0.147(5) 0.402(2) 0.845(2) 0.036(10) Uiso 1 1 d D . . . .
C1V C 0.1422(7) 0.37914(19) 0.9360(2) 0.0420(8) Uani 1 1 d . . . . .
H1V H 0.338788 0.369807 0.931613 0.050 Uiso 1 1 calc R U . . .
C2V C -0.0059(7) 0.3198(2) 0.9620(2) 0.0444(8) Uani 1 1 d . . . . .
C3V C 0.1071(9) 0.4307(2) 1.0018(3) 0.0551(10) Uani 1 1 d . . . . .
H3V H -0.089396 0.440504 1.005018 0.066 Uiso 1 1 calc R U . . .
C4V C 0.2601(12) 0.4906(3) 0.9765(4) 0.0720(13) Uani 1 1 d . . . . .
H4VC H 0.453122 0.481587 0.973313 0.108 Uiso 1 1 calc R U . . .
H4VA H 0.233087 0.522866 1.017653 0.108 Uiso 1 1 calc R U . . .
H4VB H 0.189851 0.504759 0.922757 0.108 Uiso 1 1 calc R U . . .
C5V C 0.2134(18) 0.4090(4) 1.0876(3) 0.096(2) Uani 1 1 d . . . . .
H5VC H 0.104949 0.374011 1.105863 0.143 Uiso 1 1 calc R U . . .
H5VA H 0.200214 0.443040 1.126981 0.143 Uiso 1 1 calc R U . . .
H5VB H 0.402258 0.396164 1.084297 0.143 Uiso 1 1 calc R U . . .
O1V O -0.2576(5) 0.31813(17) 0.9628(2) 0.0648(9) Uani 1 1 d . . . . .
NP N 0.1534(6) 0.27069(16) 0.9840(2) 0.0435(7) Uani 1 1 d D . . . .
HP H 0.329(5) 0.273(2) 0.991(2) 0.038(10) Uiso 1 1 d D . . . .
C1P C 0.0306(8) 0.21241(19) 1.0120(3) 0.0463(8) Uani 1 1 d . . . . .
H1P H -0.126788 0.224126 1.045660 0.056 Uiso 1 1 calc R U . . .
C2P C 0.2331(7) 0.1787(2) 1.0701(2) 0.0452(8) Uani 1 1 d . . . . .
C3P C -0.0830(8) 0.1718(2) 0.9391(3) 0.0540(9) Uani 1 1 d . . . . .
H3PA H -0.160046 0.133624 0.962215 0.065 Uiso 1 1 calc R U . . .
H3PB H -0.232513 0.194692 0.911057 0.065 Uiso 1 1 calc R U . . .
C4P C 0.1219(9) 0.1533(3) 0.8742(3) 0.0587(11) Uani 1 1 d . . . . .
C5P C 0.2489(12) 0.0952(3) 0.8775(4) 0.0765(15) Uani 1 1 d . . . . .
H5P H 0.208734 0.067184 0.920373 0.092 Uiso 1 1 calc R U . . .
C6P C 0.4372(15) 0.0778(5) 0.8174(5) 0.102(2) Uani 1 1 d . . . . .
H6P H 0.521688 0.038409 0.820176 0.123 Uiso 1 1 calc R U . . .
C7P C 0.4968(16) 0.1189(6) 0.7544(5) 0.113(3) Uani 1 1 d . . . . .
H7P H 0.620581 0.107189 0.713885 0.135 Uiso 1 1 calc R U . . .
C8P C 0.3779(17) 0.1760(6) 0.7506(4) 0.110(3) Uani 1 1 d . . . . .
H8P H 0.421991 0.203983 0.708107 0.131 Uiso 1 1 calc R U . . .
C9P C 0.1874(14) 0.1937(4) 0.8105(3) 0.0805(16) Uani 1 1 d . . . . .
H9P H 0.104471 0.233198 0.807046 0.097 Uiso 1 1 calc R U . . .
O1P O 0.4523(6) 0.1994(2) 1.0920(2) 0.0703(10) Uani 1 1 d . . . . .
O2P O 0.1342(7) 0.12471(16) 1.0963(2) 0.0657(8) Uani 1 1 d . . . . .
CMP C 0.3028(13) 0.0907(3) 1.1580(4) 0.0751(14) Uani 1 1 d . . . . .
HMPC H 0.491041 0.090875 1.141535 0.113 Uiso 1 1 calc R U . . .
HMPA H 0.238862 0.047944 1.161651 0.113 Uiso 1 1 calc R U . . .
HMPB H 0.289922 0.110734 1.211775 0.113 Uiso 1 1 calc R U . . .
OM O 0.715(2) 0.3308(7) 0.5541(7) 0.192(4) Uani 1 1 d D . . . .
HM H 0.744277 0.345246 0.507528 0.289 Uiso 1 1 calc DR U . . .
CM C 0.914(6) 0.2828(14) 0.5744(12) 0.36(2) Uani 1 1 d D . . . .
HMC H 1.094937 0.300994 0.576642 0.537 Uiso 1 1 calc DR U . . .
HMA H 0.904649 0.250512 0.532193 0.537 Uiso 1 1 calc DR U . . .
HMB H 0.875146 0.264765 0.627995 0.537 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
C6 C1 C2 119.4(4) . . ?
C6 C1 CC 118.4(5) . . ?
C2 C1 CC 122.2(5) . . ?
C1 C2 C3 119.6(5) . . ?
C4 C3 C2 120.1(5) . . ?
C4 C3 C2O 121.0(4) . . ?
C2 C3 C2O 119.0(4) . . ?
C5 C4 C3 120.1(5) . . ?
C4 C5 C6 120.2(6) . . ?
C1 C6 C5 120.6(6) . . ?
C2O O1O C5O 106.9(5) . . ?
N3O C2O O1O 117.4(5) . . ?
N3O C2O C3 126.6(4) . . ?
O1O C2O C3 116.0(5) . . ?
C2O N3O C4O 107.7(4) . . ?
N3O C4O C3B 110.9(4) . . ?
N3O C4O C5O 102.9(5) . . ?
C3B C4O C5O 115.9(4) . . ?
O1O C5O C4O 105.1(4) . . ?
C8B C3B C4B 117.7(6) . . ?
C8B C3B C4O 121.9(6) . . ?
C4B C3B C4O 120.4(5) . . ?
C5B C4B C3B 120.4(6) . . ?
C6B C5B C4B 120.5(7) . . ?
C5B C6B C7B 120.3(7) . . ?
C6B C7B C8B 120.3(6) . . ?
C3B C8B C7B 120.7(7) . . ?
OC CC NG 122.9(5) . . ?
OC CC C1 120.4(6) . . ?
NG CC C1 116.7(4) . . ?
CC NG C1G 121.0(4) . . ?
NG C1G C2G 112.5(4) . . ?
O1G C2G NV 123.5(4) . . ?
O1G C2G C1G 122.7(3) . . ?
NV C2G C1G 113.8(3) . . ?
C2G NV C1V 122.7(3) . . ?
NV C1V C2V 108.2(3) . . ?
NV C1V C3V 111.7(3) . . ?
C2V C1V C3V 110.0(3) . . ?
O1V C2V NP 123.0(4) . . ?
O1V C2V C1V 120.7(4) . . ?
NP C2V C1V 116.3(3) . . ?
C5V C3V C1V 111.1(4) . . ?
C5V C3V C4V 109.5(5) . . ?
C1V C3V C4V 110.3(4) . . ?
C2V NP C1P 120.2(3) . . ?
NP C1P C2P 109.0(3) . . ?
NP C1P C3P 112.7(3) . . ?
C2P C1P C3P 114.2(3) . . ?
O1P C2P O2P 124.0(4) . . ?
O1P C2P C1P 124.3(4) . . ?
O2P C2P C1P 111.7(3) . . ?
C4P C3P C1P 115.9(3) . . ?
C9P C4P C5P 118.1(5) . . ?
C9P C4P C3P 121.2(5) . . ?
C5P C4P C3P 120.7(5) . . ?
C4P C5P C6P 120.8(7) . . ?
C7P C6P C5P 119.7(8) . . ?
C8P C7P C6P 120.4(7) . . ?
C7P C8P C9P 120.2(8) . . ?
C4P C9P C8P 120.7(7) . . ?
C2P O2P CMP 116.4(4) . . ?
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 C6 1.380(8) . ?
C1 C2 1.392(7) . ?
C1 CC 1.501(6) . ?
C2 C3 1.403(5) . ?
C3 C4 1.386(8) . ?
C3 C2O 1.474(7) . ?
C4 C5 1.366(9) . ?
C5 C6 1.396(8) . ?
O1O C2O 1.347(5) . ?
O1O C5O 1.420(8) . ?
C2O N3O 1.262(7) . ?
N3O C4O 1.480(6) . ?
C4O C3B 1.510(8) . ?
C4O C5O 1.528(9) . ?
C3B C8B 1.374(8) . ?
C3B C4B 1.399(10) . ?
C4B C5B 1.395(10) . ?
C5B C6B 1.346(10) . ?
C6B C7B 1.360(11) . ?
C7B C8B 1.399(9) . ?
CC OC 1.225(7) . ?
CC NG 1.325(7) . ?
NG C1G 1.449(5) . ?
C1G C2G 1.513(6) . ?
C2G O1G 1.225(5) . ?
C2G NV 1.339(5) . ?
NV C1V 1.456(5) . ?
C1V C2V 1.514(5) . ?
C1V C3V 1.527(6) . ?
C2V O1V 1.224(5) . ?
C2V NP 1.336(5) . ?
C3V C5V 1.518(8) . ?
C3V C4V 1.531(7) . ?
NP C1P 1.449(5) . ?
C1P C2P 1.508(5) . ?
C1P C3P 1.533(6) . ?
C2P O1P 1.193(5) . ?
C2P O2P 1.315(5) . ?
C3P C4P 1.511(7) . ?
C4P C9P 1.373(8) . ?
C4P C5P 1.378(8) . ?
C5P C6P 1.396(9) . ?
C6P C7P 1.368(14) . ?
C7P C8P 1.342(14) . ?
C8P C9P 1.403(10) . ?
O2P CMP 1.451(6) . ?
OM CM 1.432(16) . ?
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
NV HV O1G 0.88(2) 2.13(2) 2.988(4) 167(4) 1_455 yes
NP HP O1V 0.86(2) 2.28(3) 3.062(4) 151(4) 1_655 yes
OM HM N3O 0.82 2.24 2.916(11) 139.3 . yes
