#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/53/7235323.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_7235323
loop_
_publ_author_name
'Naumova, A. S.'
'Mikhaylov, A. A.'
'Khomutova, Yu. A.'
'Novikov, R. A.'
'Arkhipov, D. E.'
'Korlyukov, A. A.'
'Ioffe, S. L.'
_publ_section_title
;
 Three-step assembly of 4-aminotetrahydropyran-2-ones from
 isoxazoline-2-oxides
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              12467
_journal_paper_doi               10.1039/c3ra47309k
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C12 H12 Br N O4'
_chemical_formula_sum            'C12 H12 Br N O4'
_chemical_formula_weight         314.14
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2850(4)
_cell_length_b                   19.1650(13)
_cell_length_c                   10.0101(7)
_cell_measurement_reflns_used    8704
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.80
_cell_measurement_theta_min      2.30
_cell_volume                     1205.74(14)
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Smart 1000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21721
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    3.415
_exptl_absorpt_correction_T_max  0.5784
_exptl_absorpt_correction_T_min  0.4704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.405
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0219P)²+0.9917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                3214
_reflns_number_total             3515
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            c3ra47309k2.cif
_cod_data_source_block           nas105
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7235323
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br -0.16144(3) 0.317302(10) 0.82560(3) 0.01784(6) Uani 1 1 d .
O1 O 0.3849(3) 0.32941(9) 0.24184(18) 0.0161(3) Uani 1 1 d .
O2 O 0.6418(3) 0.29926(10) 0.10297(18) 0.0198(3) Uani 1 1 d .
O3 O 0.6509(3) 0.46740(12) 0.0746(3) 0.0420(6) Uani 1 1 d .
O4 O 0.4428(4) 0.53692(11) 0.1816(2) 0.0354(5) Uani 1 1 d .
N1 N 0.4749(3) 0.48496(11) 0.1138(2) 0.0214(4) Uani 1 1 d .
C1 C 0.4761(4) 0.32980(11) 0.1194(2) 0.0154(4) Uani 1 1 d .
C2 C 0.3604(4) 0.37196(12) 0.0146(2) 0.0167(4) Uani 1 1 d .
H2A H 0.2390 0.3445 -0.0203 0.020 Uiso 1 1 calc R
H2B H 0.4579 0.3818 -0.0607 0.020 Uiso 1 1 calc R
C3 C 0.2788(4) 0.44063(12) 0.0723(2) 0.0161(4) Uani 1 1 d .
C4 C 0.1471(4) 0.42842(12) 0.1991(2) 0.0181(4) Uani 1 1 d .
H4A H 0.1980 0.4600 0.2705 0.022 Uiso 1 1 calc R
H4B H -0.0038 0.4398 0.1809 0.022 Uiso 1 1 calc R
C5 C 0.1629(3) 0.35301(13) 0.2473(3) 0.0139(5) Uani 1 1 d .
H5A H 0.0743 0.3226 0.1881 0.017 Uiso 1 1 calc R
C6 C 0.1645(4) 0.48443(14) -0.0326(2) 0.0195(5) Uani 1 1 d .
H6A H 0.0366 0.4598 -0.0628 0.029 Uiso 1 1 calc R
H6B H 0.2595 0.4922 -0.1088 0.029 Uiso 1 1 calc R
H6C H 0.1240 0.5294 0.0063 0.029 Uiso 1 1 calc R
C7 C 0.0892(4) 0.34478(12) 0.3894(2) 0.0153(5) Uani 1 1 d .
C8 C 0.2158(4) 0.36385(12) 0.4974(2) 0.0162(4) Uani 1 1 d .
H8A H 0.3540 0.3822 0.4816 0.019 Uiso 1 1 calc R
C9 C 0.1440(4) 0.35655(12) 0.6276(2) 0.0173(4) Uani 1 1 d .
H9A H 0.2320 0.3690 0.7009 0.021 Uiso 1 1 calc R
C10 C -0.0605(4) 0.33042(12) 0.6484(2) 0.0162(4) Uani 1 1 d .
C11 C -0.1924(4) 0.31328(12) 0.5434(2) 0.0157(4) Uani 1 1 d .
H11A H -0.3331 0.2973 0.5598 0.019 Uiso 1 1 calc R
C12 C -0.1170(4) 0.31959(11) 0.4126(2) 0.0155(4) Uani 1 1 d .
H12A H -0.2054 0.3069 0.3396 0.019 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 '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
C1 O1 C5 115.74(19)
O3 N1 O4 123.6(2)
O3 N1 C3 118.8(2)
O4 N1 C3 117.6(2)
O2 C1 O1 119.1(2)
O2 C1 C2 125.5(2)
O1 C1 C2 115.35(19)
C1 C2 C3 111.15(19)
C1 C2 H2A 109.4
C3 C2 H2A 109.4
C1 C2 H2B 109.4
C3 C2 H2B 109.4
H2A C2 H2B 108.0
C6 C3 C2 111.9(2)
C6 C3 C4 113.59(19)
C2 C3 C4 111.27(19)
C6 C3 N1 104.89(19)
C2 C3 N1 107.83(19)
C4 C3 N1 106.85(19)
C5 C4 C3 111.76(19)
C5 C4 H4A 109.3
C3 C4 H4A 109.3
C5 C4 H4B 109.3
C3 C4 H4B 109.3
H4A C4 H4B 107.9
O1 C5 C7 107.2(2)
O1 C5 C4 109.99(18)
C7 C5 C4 112.2(2)
O1 C5 H5A 109.1
C7 C5 H5A 109.1
C4 C5 H5A 109.1
C3 C6 H6A 109.5
C3 C6 H6B 109.5
H6A C6 H6B 109.5
C3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C12 119.4(2)
C8 C7 C5 122.1(2)
C12 C7 C5 118.5(2)
C9 C8 C7 121.2(2)
C9 C8 H8A 119.4
C7 C8 H8A 119.4
C8 C9 C10 118.5(2)
C8 C9 H9A 120.8
C10 C9 H9A 120.8
C11 C10 C9 121.7(2)
C11 C10 Br1 118.65(18)
C9 C10 Br1 119.64(18)
C10 C11 C12 119.4(2)
C10 C11 H11A 120.3
C12 C11 H11A 120.3
C11 C12 C7 119.9(2)
C11 C12 H12A 120.1
C7 C12 H12A 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.900(2)
O1 C1 1.353(3)
O1 C5 1.468(3)
O2 C1 1.206(3)
O3 N1 1.221(3)
O4 N1 1.222(3)
N1 C3 1.554(3)
C1 C2 1.510(3)
C2 C3 1.526(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C6 1.524(3)
C3 C4 1.534(3)
C4 C5 1.527(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C7 1.505(3)
C5 H5A 1.0000
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C8 1.391(3)
C7 C12 1.403(3)
C8 C9 1.386(3)
C8 H8A 0.9500
C9 C10 1.395(3)
C9 H9A 0.9500
C10 C11 1.378(3)
C11 C12 1.398(3)
C11 H11A 0.9500
C12 H12A 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
C5 O1 C1 O2 -166.2(2)
C5 O1 C1 C2 16.0(3)
O2 C1 C2 C3 -136.5(2)
O1 C1 C2 C3 41.2(3)
C1 C2 C3 C6 179.1(2)
C1 C2 C3 C4 -52.6(3)
C1 C2 C3 N1 64.2(2)
O3 N1 C3 C6 -106.0(3)
O4 N1 C3 C6 72.1(3)
O3 N1 C3 C2 13.4(3)
O4 N1 C3 C2 -168.5(2)
O3 N1 C3 C4 133.1(2)
O4 N1 C3 C4 -48.8(3)
C6 C3 C4 C5 136.9(2)
C2 C3 C4 C5 9.5(3)
N1 C3 C4 C5 -108.0(2)
C1 O1 C5 C7 176.91(19)
C1 O1 C5 C4 -60.9(3)
C3 C4 C5 O1 44.4(3)
C3 C4 C5 C7 163.62(19)
O1 C5 C7 C8 43.1(3)
C4 C5 C7 C8 -77.7(3)
O1 C5 C7 C12 -139.43(19)
C4 C5 C7 C12 99.7(2)
C12 C7 C8 C9 1.9(3)
C5 C7 C8 C9 179.3(2)
C7 C8 C9 C10 -0.9(4)
C8 C9 C10 C11 -1.3(3)
C8 C9 C10 Br1 178.29(18)
C9 C10 C11 C12 2.5(3)
Br1 C10 C11 C12 -177.08(17)
C10 C11 C12 C7 -1.5(3)
C8 C7 C12 C11 -0.6(3)
C5 C7 C12 C11 -178.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339245
