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#$Date: 2026-02-20 03:08:57 +0100 (Fri 20 de Feb de 2026) $
#$Revision: 304563 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/10/7161012.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_7161012
loop_
_publ_author_name
'Azimi, Rayhaneh'
'Amiri, Kamran'
'Hosseini, S. Sina'
'Stranger, Rob'
'Ariafard, Alireza'
'Rominger, Frank'
'Bijanzadeh, Hamid Reza'
'Balalaie, Saeed'
_publ_section_title
;
 Synthesis of oxaprozin analogs from 2H-azirines and cyclic anhydrides
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D6OB00168H
_journal_year                    2025
_chemical_formula_sum            'C19 H17 N O3'
_chemical_formula_weight         307.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-11-07 deposited with the CCDC.	2026-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.8750(18)
_cell_angle_beta                 98.3576(17)
_cell_angle_gamma                90.9987(19)
_cell_formula_units_Z            2
_cell_length_a                   6.1263(5)
_cell_length_b                   10.1800(8)
_cell_length_c                   12.5965(10)
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.52
_cell_volume                     776.03(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10920
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.827
_diffrn_reflns_theta_min         1.636
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_correction_T_min  0.7449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       plank
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0470
_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)+(0.0358P)²+0.1716P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1072
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2317
_reflns_number_total             3292
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ob00168h2.cif
_cod_data_source_block           sba205
_cod_database_code               7161012
_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. 
;
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.5481(3) 0.74515(16) 0.73815(13) 0.0265(4) Uani 1 1 d . . . . .
C2 C 0.6682(3) 0.66363(16) 0.68336(13) 0.0271(4) Uani 1 1 d . . . . .
C4 C 0.4136(3) 0.75001(17) 0.57101(14) 0.0296(4) Uani 1 1 d . . . . .
O3 O 0.58291(19) 0.66639(11) 0.57510(9) 0.0293(4) Uani 0.894(15) 1 d . . P A 1
N5 N 0.3848(2) 0.79933(13) 0.66505(11) 0.0303(4) Uani 0.894(15) 1 d . . P A 1
N3B N 0.58291(19) 0.66639(11) 0.57510(9) 0.0293(4) Uani 0.106(15) 1 d . . P A 2
O5B O 0.3848(2) 0.79933(13) 0.66505(11) 0.0303(4) Uani 0.106(15) 1 d . . P A 2
C6 C 0.2803(3) 0.77420(18) 0.46643(13) 0.0324(4) Uani 1 1 d . . . . .
H6A H 0.148106 0.823277 0.480025 0.039 Uiso 1 1 calc R U . . .
H6B H 0.228666 0.688358 0.430224 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4007(3) 0.85085(18) 0.39023(13) 0.0315(4) Uani 1 1 d . . . . .
H7A H 0.486364 0.925318 0.430735 0.038 Uiso 1 1 calc R U . . .
H7B H 0.505121 0.792675 0.358825 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2360(3) 0.90281(18) 0.30073(13) 0.0334(4) Uani 1 1 d . . . . .
H8A H 0.317385 0.938929 0.245895 0.040 Uiso 1 1 calc R U . . .
H8B H 0.140136 0.828963 0.265782 0.040 Uiso 1 1 calc R U . . .
C9 C 0.0936(3) 1.00834(17) 0.34068(13) 0.0280(4) Uani 1 1 d . . . . .
O9 O 0.1456(2) 1.07767(12) 0.42043(10) 0.0381(3) Uani 1 1 d . . . . .
O10 O -0.0950(2) 1.01868(14) 0.27565(10) 0.0445(4) Uani 1 1 d . . . . .
H10 H -0.181(4) 1.082(2) 0.3009(17) 0.067 Uiso 1 1 d . U . . .
C11 C 0.5662(3) 0.78070(16) 0.85419(13) 0.0263(4) Uani 1 1 d . . . . .
C12 C 0.3861(3) 0.76165(18) 0.90733(14) 0.0348(4) Uani 1 1 d . . . . .
H12 H 0.252325 0.724429 0.869197 0.042 Uiso 1 1 calc R U . . .
C13 C 0.4008(3) 0.79681(19) 1.01601(15) 0.0395(5) Uani 1 1 d . . . . .
H13 H 0.277063 0.783095 1.052048 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5932(3) 0.85142(18) 1.07193(14) 0.0358(4) Uani 1 1 d . . . . .
H14 H 0.602110 0.876314 1.146159 0.043 Uiso 1 1 calc R U . . .
C15 C 0.7734(3) 0.86984(18) 1.01960(14) 0.0338(4) Uani 1 1 d . . . . .
H15 H 0.906921 0.907015 1.058094 0.041 Uiso 1 1 calc R U . . .
C16 C 0.7606(3) 0.83445(17) 0.91142(14) 0.0307(4) Uani 1 1 d . . . . .
H16 H 0.885571 0.847010 0.876062 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8530(3) 0.57757(16) 0.71262(13) 0.0272(4) Uani 1 1 d . . . . .
C22 C 0.8807(3) 0.51897(18) 0.81110(15) 0.0366(5) Uani 1 1 d . . . . .
H22 H 0.776878 0.533464 0.859355 0.044 Uiso 1 1 calc R U . . .
C23 C 1.0589(3) 0.43978(19) 0.83884(16) 0.0448(5) Uani 1 1 d . . . . .
H23 H 1.077882 0.400591 0.906342 0.054 Uiso 1 1 calc R U . . .
C24 C 1.2094(3) 0.41754(19) 0.76859(17) 0.0445(5) Uani 1 1 d . . . . .
H24 H 1.332400 0.363749 0.788205 0.053 Uiso 1 1 calc R U . . .
C25 C 1.1817(3) 0.47301(19) 0.67034(16) 0.0399(5) Uani 1 1 d . . . . .
H25 H 1.283921 0.456213 0.621636 0.048 Uiso 1 1 calc R U . . .
C26 C 1.0049(3) 0.55328(17) 0.64251(14) 0.0325(4) Uani 1 1 d . . . . .
H26 H 0.987184 0.592163 0.574892 0.039 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 0.0033 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
C2 C1 O5B 108.60(14) . . ?
C2 C1 N5 108.60(14) . . ?
C2 C1 C11 130.87(15) . . ?
O5B C1 C11 120.53(14) . . ?
N5 C1 C11 120.53(14) . . ?
C1 C2 N3B 107.49(14) . . ?
C1 C2 O3 107.49(14) . . ?
C1 C2 C21 135.04(16) . . ?
N3B C2 C21 117.46(14) . . ?
O3 C2 C21 117.46(14) . . ?
N5 C4 O3 113.13(14) . . ?
O5B C4 N3B 113.13(14) . . ?
O5B C4 C6 127.02(16) . . ?
N5 C4 C6 127.02(16) . . ?
O3 C4 C6 119.83(15) . . ?
N3B C4 C6 119.83(15) . . ?
C4 O3 C2 105.24(12) . . ?
C4 N5 C1 105.54(14) . . ?
C4 N3B C2 105.24(12) . . ?
C4 O5B C1 105.54(14) . . ?
C4 C6 C7 114.90(15) . . ?
C4 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C4 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 110.31(14) . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 112.71(14) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O9 C9 O10 123.35(16) . . ?
O9 C9 C8 124.45(16) . . ?
O10 C9 C8 112.18(15) . . ?
C9 O10 H10 111.8(14) . . ?
C12 C11 C16 119.05(16) . . ?
C12 C11 C1 119.84(16) . . ?
C16 C11 C1 121.10(15) . . ?
C11 C12 C13 120.18(17) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.42(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.64(17) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.30(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.39(16) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C26 C21 C22 118.92(16) . . ?
C26 C21 C2 120.35(15) . . ?
C22 C21 C2 120.73(15) . . ?
C23 C22 C21 120.20(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.13(18) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.21(18) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.93(18) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.59(17) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
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 1.348(2) . ?
C1 O5B 1.398(2) . ?
C1 N5 1.398(2) . ?
C1 C11 1.476(2) . ?
C2 N3B 1.3896(19) . ?
C2 O3 1.3896(19) . ?
C2 C21 1.460(2) . ?
C4 O5B 1.300(2) . ?
C4 N5 1.300(2) . ?
C4 O3 1.350(2) . ?
C4 N3B 1.350(2) . ?
C4 C6 1.480(2) . ?
C6 C7 1.528(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.522(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.508(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O9 1.1987(19) . ?
C9 O10 1.325(2) . ?
O10 H10 0.91(2) . ?
C11 C12 1.387(2) . ?
C11 C16 1.388(2) . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.390(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
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
O5B C1 C2 N3B 0.45(19) . . . . ?
C11 C1 C2 N3B -179.49(17) . . . . ?
N5 C1 C2 O3 0.45(19) . . . . ?
C11 C1 C2 O3 -179.49(17) . . . . ?
O5B C1 C2 C21 -178.18(18) . . . . ?
N5 C1 C2 C21 -178.18(18) . . . . ?
C11 C1 C2 C21 1.9(3) . . . . ?
N5 C4 O3 C2 -0.03(19) . . . . ?
C6 C4 O3 C2 -178.58(15) . . . . ?
C1 C2 O3 C4 -0.27(18) . . . . ?
C21 C2 O3 C4 178.64(14) . . . . ?
O3 C4 N5 C1 0.29(19) . . . . ?
C6 C4 N5 C1 178.72(17) . . . . ?
C2 C1 N5 C4 -0.46(19) . . . . ?
C11 C1 N5 C4 179.48(16) . . . . ?
O5B C4 N3B C2 -0.03(19) . . . . ?
C6 C4 N3B C2 -178.58(15) . . . . ?
C1 C2 N3B C4 -0.27(18) . . . . ?
C21 C2 N3B C4 178.64(14) . . . . ?
N3B C4 O5B C1 0.29(19) . . . . ?
C6 C4 O5B C1 178.72(17) . . . . ?
C2 C1 O5B C4 -0.46(19) . . . . ?
C11 C1 O5B C4 179.48(16) . . . . ?
O5B C4 C6 C7 112.5(2) . . . . ?
N5 C4 C6 C7 112.5(2) . . . . ?
O3 C4 C6 C7 -69.2(2) . . . . ?
N3B C4 C6 C7 -69.2(2) . . . . ?
C4 C6 C7 C8 -164.27(15) . . . . ?
C6 C7 C8 C9 68.1(2) . . . . ?
C7 C8 C9 O9 25.1(3) . . . . ?
C7 C8 C9 O10 -156.70(15) . . . . ?
C2 C1 C11 C12 -123.6(2) . . . . ?
O5B C1 C11 C12 56.5(2) . . . . ?
N5 C1 C11 C12 56.5(2) . . . . ?
C2 C1 C11 C16 57.1(3) . . . . ?
O5B C1 C11 C16 -122.86(18) . . . . ?
N5 C1 C11 C16 -122.86(18) . . . . ?
C16 C11 C12 C13 0.4(3) . . . . ?
C1 C11 C12 C13 -178.95(16) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C12 C11 C16 C15 -0.7(2) . . . . ?
C1 C11 C16 C15 178.61(15) . . . . ?
C1 C2 C21 C26 -149.9(2) . . . . ?
N3B C2 C21 C26 31.6(2) . . . . ?
O3 C2 C21 C26 31.6(2) . . . . ?
C1 C2 C21 C22 29.8(3) . . . . ?
N3B C2 C21 C22 -148.70(16) . . . . ?
O3 C2 C21 C22 -148.70(16) . . . . ?
C26 C21 C22 C23 1.0(3) . . . . ?
C2 C21 C22 C23 -178.67(17) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C24 C25 C26 1.2(3) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C22 C21 C26 C25 -0.5(3) . . . . ?
C2 C21 C26 C25 179.26(16) . . . . ?
