#------------------------------------------------------------------------------
#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/63/7116335.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_7116335
loop_
_publ_author_name
'Raymond C. F. Jones'
'Alexander Chatterley'
'Romain Marty'
'W. Martin Owton'
'Mark R. J. Elsegood'
_publ_section_title
;
 Isoxazole to oxazole: a mild and unexpected transformation
;
_journal_name_full               Chem.Commun.
_journal_page_first              1112
_journal_paper_doi               10.1039/C4cc07999J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C13 H13 N O4'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_audit_update_record
;
2013-09-24 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.7388(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5001(6)
_cell_length_b                   15.2463(18)
_cell_length_c                   13.6680(16)
_cell_measurement_reflns_used    6269
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.67
_cell_volume                     1135.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.578
_diffrn_reflns_theta_min         2.011
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2009/1, Sheldrick, G.M., (2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          1.020
_exptl_crystal_size_mid          0.790
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0451
_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)+(0.0800P)²+0.2403P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2970
_reflns_number_total             3446
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4cc07999j2.cif
_cod_data_source_block           7a
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               7116335
_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. 
;
_shelx_estimated_absorpt_t_min   0.898
_shelx_estimated_absorpt_t_max   0.960
_shelxl_version_number           2012-6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.13899(18) 0.50029(6) 0.73465(7) 0.0213(2) Uani 1 1 d . . . . .
C2 C 0.02346(19) 0.50237(6) 0.81767(7) 0.0225(2) Uani 1 1 d . . . A .
O1 O -0.16208(15) 0.45174(5) 0.83427(6) 0.02943(19) Uani 1 1 d . . . . .
H1A H -0.198(4) 0.4131(14) 0.7766(16) 0.061(6) Uiso 1 1 d . . . . .
C3 C 0.1069(2) 0.56371(7) 0.90150(8) 0.0280(2) Uani 1 1 d . U . . .
H3A H 0.2256 0.5326 0.9504 0.034 Uiso 0.855(4) 1 calc R U P A 1
H3B H -0.0362 0.5799 0.9345 0.034 Uiso 0.855(4) 1 calc R U P A 1
H3C H 0.0893 0.5343 0.9647 0.034 Uiso 0.145(4) 1 calc R U P A 2
H3D H 0.0002 0.6163 0.8959 0.034 Uiso 0.145(4) 1 calc R U P A 2
C4 C 0.2250(2) 0.64604(8) 0.86986(9) 0.0264(3) Uani 0.855(4) 1 d . U P A 1
H4A H 0.2959 0.6797 0.9288 0.032 Uiso 0.855(4) 1 calc R U P A 1
H4B H 0.1001 0.6831 0.8306 0.032 Uiso 0.855(4) 1 calc R U P A 1
C5 C 0.4284(2) 0.62229(8) 0.80740(8) 0.0286(2) Uani 1 1 d . U . . .
H5A H 0.4873 0.6766 0.7786 0.034 Uiso 0.855(4) 1 calc R U P A 1
H5B H 0.5682 0.5962 0.8509 0.034 Uiso 0.855(4) 1 calc R U P A 1
H5C H 0.6080 0.6305 0.8114 0.034 Uiso 0.145(4) 1 calc R U P A 2
H5D H 0.3490 0.6798 0.7920 0.034 Uiso 0.145(4) 1 calc R U P A 2
C6 C 0.34399(19) 0.55883(7) 0.72539(8) 0.0233(2) Uani 1 1 d . . . A .
O2 O 0.44831(16) 0.55463(6) 0.65078(6) 0.03044(19) Uani 1 1 d . . . . .
C4X C 0.3702(14) 0.5919(6) 0.9025(6) 0.0293(19) Uani 0.145(4) 1 d . U P A 2
H4C H 0.4064 0.6397 0.9514 0.035 Uiso 0.145(4) 1 calc R U P A 2
H4D H 0.4787 0.5419 0.9245 0.035 Uiso 0.145(4) 1 calc R U P A 2
N1 N 0.08777(17) 0.44484(6) 0.65030(6) 0.02339(19) Uani 1 1 d . . . . .
H1 H 0.186(3) 0.4568(11) 0.6036(13) 0.042(4) Uiso 1 1 d . . . . .
C7 C -0.07395(19) 0.37978(7) 0.62977(7) 0.0233(2) Uani 1 1 d . . . . .
O3 O -0.21874(18) 0.35540(7) 0.68811(7) 0.0408(2) Uani 1 1 d . . . . .
C8 C -0.07667(18) 0.33236(6) 0.53416(7) 0.0215(2) Uani 1 1 d . . . . .
C9 C 0.09244(18) 0.34448(7) 0.46663(7) 0.0227(2) Uani 1 1 d . . . . .
O4 O 0.26533(15) 0.40812(6) 0.48428(6) 0.02946(19) Uani 1 1 d . . . . .
H4 H 0.356(3) 0.4140(12) 0.4339(14) 0.050(5) Uiso 1 1 d . . . . .
C10 C 0.0831(2) 0.29043(7) 0.38345(8) 0.0265(2) Uani 1 1 d . . . . .
H10 H 0.203(3) 0.2996(11) 0.3378(11) 0.033(4) Uiso 1 1 d . . . . .
C11 C -0.0971(2) 0.22665(7) 0.36500(8) 0.0289(2) Uani 1 1 d . . . . .
H11 H -0.101(3) 0.1888(11) 0.3065(12) 0.039(4) Uiso 1 1 d . . . . .
C12 C -0.2721(2) 0.21606(7) 0.42901(8) 0.0297(2) Uani 1 1 d . . . . .
H12 H -0.411(3) 0.1685(9) 0.4077(11) 0.026(3) Uiso 1 1 d . . . . .
C13 C -0.25934(19) 0.26839(7) 0.51249(8) 0.0257(2) Uani 1 1 d . . . . .
H13 H -0.374(3) 0.2599(10) 0.5589(11) 0.030(3) Uiso 1 1 d . . . . .
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
C2 C1 N1 128.19(9)
C2 C1 C6 120.47(9)
N1 C1 C6 111.33(8)
O1 C2 C1 125.55(9)
O1 C2 C3 113.33(9)
C1 C2 C3 121.11(9)
C2 O1 H1A 106.8(12)
C2 C3 C4 113.57(9)
C2 C3 C4X 112.3(3)
C2 C3 H3A 108.9
C4 C3 H3A 108.9
C2 C3 H3B 108.9
C4 C3 H3B 108.9
H3A C3 H3B 107.7
C2 C3 H3C 109.2
C4X C3 H3C 109.2
C2 C3 H3D 109.2
C4X C3 H3D 109.2
H3C C3 H3D 107.9
C3 C4 C5 109.72(10)
C3 C4 H4A 109.7
C5 C4 H4A 109.7
C3 C4 H4B 109.7
C5 C4 H4B 109.7
H4A C4 H4B 108.2
C4X C5 C6 112.2(3)
C6 C5 C4 112.96(9)
C6 C5 H5A 109.0
C4 C5 H5A 109.0
C6 C5 H5B 109.0
C4 C5 H5B 109.0
H5A C5 H5B 107.8
C4X C5 H5C 109.2
C6 C5 H5C 109.2
C4X C5 H5D 109.2
C6 C5 H5D 109.2
H5C C5 H5D 107.9
O2 C6 C1 119.35(9)
O2 C6 C5 121.07(9)
C1 C6 C5 119.57(9)
C5 C4X C3 114.1(5)
C5 C4X H4C 108.7
C3 C4X H4C 108.7
C5 C4X H4D 108.7
C3 C4X H4D 108.7
H4C C4X H4D 107.6
C7 N1 C1 131.51(9)
C7 N1 H1 116.2(11)
C1 N1 H1 112.2(11)
O3 C7 N1 123.16(10)
O3 C7 C8 118.69(9)
N1 C7 C8 118.13(9)
C13 C8 C9 118.06(9)
C13 C8 C7 116.38(9)
C9 C8 C7 125.53(9)
O4 C9 C10 120.91(9)
O4 C9 C8 119.09(9)
C10 C9 C8 120.00(9)
C9 O4 H4 112.3(12)
C11 C10 C9 120.52(10)
C11 C10 H10 120.8(9)
C9 C10 H10 118.6(9)
C10 C11 C12 120.24(10)
C10 C11 H11 119.7(10)
C12 C11 H11 120.0(10)
C13 C12 C11 119.15(10)
C13 C12 H12 124.9(8)
C11 C12 H12 115.9(8)
C12 C13 C8 121.95(10)
C12 C13 H13 120.1(9)
C8 C13 H13 117.9(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3735(14)
C1 N1 1.4268(12)
C1 C6 1.4568(14)
C2 O1 1.3233(13)
C2 C3 1.5022(14)
O1 H1A 0.98(2)
C3 C4 1.5033(17)
C3 C4X 1.509(8)
C3 H3A 0.9900
C3 H3B 0.9900
C3 H3C 0.9900
C3 H3D 0.9900
C4 C5 1.5387(16)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C4X 1.455(8)
C5 C6 1.5059(15)
C5 H5A 0.9900
C5 H5B 0.9900
C5 H5C 0.9900
C5 H5D 0.9900
C6 O2 1.2373(13)
C4X H4C 0.9900
C4X H4D 0.9900
N1 C7 1.3366(13)
N1 H1 0.908(18)
C7 O3 1.2567(13)
C7 C8 1.4917(14)
C8 C13 1.4030(14)
C8 C9 1.4079(14)
C9 O4 1.3573(12)
C9 C10 1.3995(14)
O4 H4 0.908(19)
C10 C11 1.3869(16)
C10 H10 0.979(16)
C11 C12 1.3945(16)
C11 H11 0.984(17)
C12 C13 1.3863(15)
C12 H12 1.066(14)
C13 H13 0.962(15)
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
O1 H1A N1 0.98(2) 2.53(2) 3.0254(12) 110.9(14) .
O1 H1A O3 0.98(2) 1.49(2) 2.4653(12) 172.7(19) .
N1 H1 O2 0.908(18) 2.116(17) 2.5944(12) 111.8(13) .
N1 H1 O4 0.908(18) 1.895(18) 2.6481(12) 139.0(15) .
O4 H4 O2 0.908(19) 1.75(2) 2.6446(11) 168.2(18) 3_666
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
N1 C1 C2 O1 -0.19(17)
C6 C1 C2 O1 -179.24(9)
N1 C1 C2 C3 178.13(10)
C6 C1 C2 C3 -0.93(15)
O1 C2 C3 C4 -153.17(10)
C1 C2 C3 C4 28.33(14)
O1 C2 C3 C4X 156.0(4)
C1 C2 C3 C4X -22.5(4)
C2 C3 C4 C5 -51.74(13)
C4X C3 C4 C5 47.2(4)
C3 C4 C5 C4X -49.4(4)
C3 C4 C5 C6 50.13(13)
C2 C1 C6 O2 178.62(10)
N1 C1 C6 O2 -0.58(13)
C2 C1 C6 C5 -0.32(15)
N1 C1 C6 C5 -179.52(9)
C4X C5 C6 O2 -153.0(4)
C4 C5 C6 O2 155.99(11)
C4X C5 C6 C1 25.9(4)
C4 C5 C6 C1 -25.09(14)
C6 C5 C4X C3 -50.0(6)
C4 C5 C4X C3 51.3(4)
C2 C3 C4X C5 48.8(6)
C4 C3 C4X C5 -53.2(4)
C2 C1 N1 C7 -2.57(18)
C6 C1 N1 C7 176.55(10)
C1 N1 C7 O3 -0.25(18)
C1 N1 C7 C8 -178.40(9)
O3 C7 C8 C13 5.76(15)
N1 C7 C8 C13 -176.02(9)
O3 C7 C8 C9 -171.92(10)
N1 C7 C8 C9 6.31(15)
C13 C8 C9 O4 177.67(9)
C7 C8 C9 O4 -4.69(15)
C13 C8 C9 C10 -3.26(15)
C7 C8 C9 C10 174.38(10)
O4 C9 C10 C11 -178.79(10)
C8 C9 C10 C11 2.16(16)
C9 C10 C11 C12 0.40(17)
C10 C11 C12 C13 -1.76(17)
C11 C12 C13 C8 0.58(17)
C9 C8 C13 C12 1.92(16)
C7 C8 C13 C12 -175.94(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139185762
