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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/86/1508668.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_1508668
loop_
_publ_author_name
'Mo, Dong-Liang'
'Wink, Donald A.'
'Anderson, Laura L.'
_publ_section_title
;
 Preparation and rearrangement of N-vinyl nitrones: synthesis of
 spiroisoxazolines and fluorene-tethered isoxazoles.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5180
_journal_page_last               5183
_journal_paper_doi               10.1021/ol3022885
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.4540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1767(7)
_cell_length_b                   13.3547(7)
_cell_length_c                   10.3670(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1667.52(16)
_computing_cell_refinement       'SAINT (Bruker)'
_computing_data_collection       'SMART (Bruker)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15148
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.69
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0912P)²+0.2552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                2977
_reflns_number_total             3881
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3022885_si_002.cif
_cod_data_source_block           compound3g
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1508668
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N14 N 0.40021(11) 0.20036(10) 0.55481(12) 0.0443(3) Uani 1 1 d .
O15 O 0.39820(11) 0.27206(10) 0.47076(13) 0.0648(4) Uani 1 1 d .
C10 C 0.29631(12) 0.07418(11) 0.67382(14) 0.0408(3) Uani 1 1 d .
C9 C 0.30828(12) 0.15947(11) 0.58504(14) 0.0414(3) Uani 1 1 d .
C13 C 0.19700(13) 0.19323(12) 0.52958(15) 0.0451(4) Uani 1 1 d .
C16 C 0.51099(12) 0.16972(11) 0.61216(14) 0.0418(3) Uani 1 1 d .
C17 C 0.58041(13) 0.12988(13) 0.51784(15) 0.0486(4) Uani 1 1 d .
H17A H 0.5757 0.1745 0.4434 0.058 Uiso 1 1 calc R
H17B H 0.5522 0.0649 0.4868 0.058 Uiso 1 1 calc R
C12 C 0.12037(13) 0.13272(12) 0.58320(15) 0.0473(4) Uani 1 1 d .
O22 O 0.82037(10) 0.05703(11) 0.77063(14) 0.0682(4) Uani 1 1 d .
C8 C 0.16020(15) 0.26889(14) 0.44165(16) 0.0549(4) Uani 1 1 d .
H8 H 0.2103 0.3091 0.4059 0.066 Uiso 1 1 calc R
C18 C 0.70158(13) 0.11949(13) 0.58001(17) 0.0529(4) Uani 1 1 d .
H18A H 0.7404 0.0758 0.5270 0.063 Uiso 1 1 calc R
H18B H 0.7373 0.1846 0.5842 0.063 Uiso 1 1 calc R
C11 C 0.18140(13) 0.05983(12) 0.67134(15) 0.0452(4) Uani 1 1 d .
C19 C 0.70814(13) 0.07656(13) 0.71581(17) 0.0508(4) Uani 1 1 d .
C1 C 0.37012(14) 0.01086(12) 0.74889(15) 0.0487(4) Uani 1 1 d .
H1 H 0.4462 0.0187 0.7507 0.058 Uiso 1 1 calc R
C21 C 0.54315(14) 0.18230(14) 0.73832(16) 0.0550(4) Uani 1 1 d .
H21 H 0.4957 0.2135 0.7884 0.066 Uiso 1 1 calc R
C5 C 0.00734(14) 0.14749(16) 0.54891(19) 0.0625(5) Uani 1 1 d .
H5 H -0.0434 0.1073 0.5837 0.075 Uiso 1 1 calc R
C20 C 0.65475(16) 0.14720(17) 0.80208(18) 0.0676(5) Uani 1 1 d .
H20A H 0.6469 0.1135 0.8831 0.081 Uiso 1 1 calc R
H20B H 0.7027 0.2047 0.8229 0.081 Uiso 1 1 calc R
C6 C -0.02863(16) 0.22298(17) 0.4622(2) 0.0701(5) Uani 1 1 d .
H6 H -0.1044 0.2340 0.4392 0.084 Uiso 1 1 calc R
C4 C 0.14162(15) -0.01530(14) 0.74438(19) 0.0598(5) Uani 1 1 d .
H4 H 0.0656 -0.0241 0.7424 0.072 Uiso 1 1 calc R
C2 C 0.32948(17) -0.06412(14) 0.82105(18) 0.0608(5) Uani 1 1 d .
H2 H 0.3789 -0.1068 0.8711 0.073 Uiso 1 1 calc R
C3 C 0.21615(18) -0.07673(15) 0.8200(2) 0.0692(6) Uani 1 1 d .
H3 H 0.1905 -0.1267 0.8704 0.083 Uiso 1 1 calc R
C7 C 0.04612(16) 0.28269(16) 0.40870(18) 0.0650(5) Uani 1 1 d .
H7 H 0.0197 0.3328 0.3499 0.078 Uiso 1 1 calc R
O25 O 0.65384(11) -0.01772(10) 0.70306(14) 0.0691(4) Uani 1 1 d .
C24 C 0.71489(17) -0.08345(17) 0.7940(2) 0.0763(6) Uani 1 1 d .
H24A H 0.7122 -0.1515 0.7611 0.092 Uiso 1 1 calc R
H24B H 0.6866 -0.0824 0.8767 0.092 Uiso 1 1 calc R
C23 C 0.82974(19) -0.0428(2) 0.8081(3) 0.1002(9) Uani 1 1 d .
H23A H 0.8655 -0.0484 0.8978 0.120 Uiso 1 1 calc R
H23B H 0.8735 -0.0794 0.7529 0.120 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O15 N14 C9 122.16(13)
O15 N14 C16 114.18(12)
C9 N14 C16 123.66(13)
C1 C10 C11 119.17(14)
C1 C10 C9 134.51(14)
C11 C10 C9 106.30(13)
N14 C9 C13 123.11(14)
N14 C9 C10 128.80(14)
C13 C9 C10 108.08(12)
C8 C13 C12 120.48(15)
C8 C13 C9 132.25(15)
C12 C13 C9 107.28(13)
C21 C16 N14 119.53(13)
C21 C16 C17 125.78(15)
N14 C16 C17 114.64(13)
C16 C17 C18 111.32(13)
C5 C12 C13 120.54(16)
C5 C12 C11 130.60(16)
C13 C12 C11 108.86(13)
C23 O22 C19 108.77(15)
C13 C8 C7 118.08(17)
C19 C18 C17 110.06(13)
C4 C11 C10 120.95(16)
C4 C11 C12 129.58(15)
C10 C11 C12 109.47(13)
O25 C19 O22 106.33(14)
O25 C19 C20 111.96(15)
O22 C19 C20 110.43(14)
O25 C19 C18 106.84(14)
O22 C19 C18 110.93(13)
C20 C19 C18 110.25(15)
C2 C1 C10 119.39(15)
C16 C21 C20 121.05(14)
C6 C5 C12 118.71(17)
C21 C20 C19 112.08(14)
C5 C6 C7 121.15(18)
C3 C4 C11 119.16(17)
C1 C2 C3 121.16(18)
C4 C3 C2 120.16(17)
C6 C7 C8 121.04(18)
C24 O25 C19 107.22(15)
O25 C24 C23 103.47(17)
O22 C23 C24 106.60(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N14 O15 1.2925(17)
N14 C9 1.3239(19)
N14 C16 1.4508(19)
C10 C1 1.387(2)
C10 C11 1.409(2)
C10 C9 1.485(2)
C9 C13 1.463(2)
C13 C8 1.390(2)
C13 C12 1.409(2)
C16 C21 1.320(2)
C16 C17 1.482(2)
C17 C18 1.527(2)
C12 C5 1.384(2)
C12 C11 1.461(2)
O22 C23 1.389(3)
O22 C19 1.4249(19)
C8 C7 1.393(3)
C18 C19 1.511(2)
C11 C4 1.386(2)
C19 O25 1.419(2)
C19 C20 1.511(3)
C1 C2 1.384(2)
C21 C20 1.496(3)
C5 C6 1.379(3)
C6 C7 1.386(3)
C4 C3 1.379(3)
C2 C3 1.389(3)
O25 C24 1.417(2)
C24 C23 1.487(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 134845978
