#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/55/7125556.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_7125556
loop_
_publ_author_name
'Henderson, Alistair P.'
'Mutlu, Esra'
'Leclercq, Amélie'
'Bleasdale, Christine'
'Clegg, William'
'Henderson, Richard A.'
'Golding, Bernard T.'
_publ_section_title
;
 Trapping of benzene oxide-oxepin and methyl-substituted derivatives with
 4-phenyl- and 4-pentafluorophenyl-1,2,4-triazoline-3,5-dione.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1956
_journal_page_last               1957
_journal_paper_doi               10.1039/b205079j
_journal_year                    2002
_chemical_formula_sum            'C14 H11 N3 O3'
_chemical_formula_weight         269.26
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   10.8897(7)
_cell_length_b                   14.2214(9)
_cell_length_c                   15.2607(10)
_cell_measurement_reflns_used    18837
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      2.28
_cell_volume                     2363.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      160(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17468
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0383
_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)+(0.0542P)²+1.0063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2399
_reflns_number_total             2845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b205079j.txt
_cod_data_source_block           btg45
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7125556
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.01483(13) 0.36433(9) 0.42577(8) 0.0248(3) Uani 1 1 d .
H1 H 0.0086 0.4044 0.3737 0.030 Uiso 1 1 calc R
C2 C 0.14131(13) 0.36634(10) 0.46495(9) 0.0293(3) Uani 1 1 d .
H2 H 0.2049 0.4024 0.4421 0.035 Uiso 1 1 calc R
C3 C 0.15420(13) 0.31193(10) 0.53516(9) 0.0286(3) Uani 1 1 d .
H3 H 0.2276 0.3065 0.5659 0.034 Uiso 1 1 calc R
C4 C 0.03933(13) 0.26017(9) 0.56011(8) 0.0234(3) Uani 1 1 d .
H4 H 0.0514 0.2206 0.6120 0.028 Uiso 1 1 calc R
C5 C -0.06774(13) 0.32903(9) 0.57184(9) 0.0264(3) Uani 1 1 d .
H5 H -0.1418 0.3072 0.6022 0.032 Uiso 1 1 calc R
C6 C -0.08185(13) 0.38933(9) 0.49487(9) 0.0263(3) Uani 1 1 d .
H6 H -0.1647 0.4063 0.4755 0.032 Uiso 1 1 calc R
O1 O -0.03666(10) 0.42691(7) 0.57622(6) 0.0308(2) Uani 1 1 d .
N1 N 0.00071(10) 0.20386(7) 0.48173(6) 0.0203(2) Uani 1 1 d .
N2 N -0.01551(10) 0.26304(7) 0.40569(7) 0.0221(2) Uani 1 1 d .
C7 C 0.07277(11) 0.12755(8) 0.45777(8) 0.0192(2) Uani 1 1 d .
C8 C 0.04302(12) 0.21932(9) 0.33580(8) 0.0233(3) Uani 1 1 d .
O2 O 0.05074(11) 0.24933(7) 0.26183(6) 0.0348(3) Uani 1 1 d .
O3 O 0.11307(9) 0.06773(6) 0.50613(6) 0.0245(2) Uani 1 1 d .
N3 N 0.08596(10) 0.13306(7) 0.36678(6) 0.0207(2) Uani 1 1 d .
C9 C 0.14416(11) 0.06316(9) 0.31341(8) 0.0202(2) Uani 1 1 d .
C10 C 0.11377(12) -0.03055(9) 0.32584(9) 0.0241(3) Uani 1 1 d .
H10 H 0.0561 -0.0479 0.3678 0.029 Uiso 1 1 calc R
C11 C 0.17134(14) -0.09811(10) 0.27434(9) 0.0298(3) Uani 1 1 d .
H11 H 0.1533 -0.1614 0.2827 0.036 Uiso 1 1 calc R
C12 C 0.25521(14) -0.07195(11) 0.21087(9) 0.0323(3) Uani 1 1 d .
H12 H 0.2929 -0.1176 0.1765 0.039 Uiso 1 1 calc R
C13 C 0.28312(14) 0.02185(11) 0.19843(9) 0.0323(3) Uani 1 1 d .
H13 H 0.3387 0.0392 0.1551 0.039 Uiso 1 1 calc R
C14 C 0.22861(13) 0.09026(10) 0.25021(8) 0.0273(3) Uani 1 1 d .
H14 H 0.2484 0.1534 0.2427 0.033 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
C2 C1 N2 107.44(11)
C2 C1 C6 110.59(11)
N2 C1 C6 102.17(10)
C3 C2 C1 114.00(12)
C2 C3 C4 113.71(12)
N1 C4 C3 107.06(10)
N1 C4 C5 102.76(10)
C3 C4 C5 110.51(11)
O1 C5 C6 59.54(8)
O1 C5 C4 116.48(12)
C6 C5 C4 111.14(11)
O1 C6 C5 59.25(8)
O1 C6 C1 116.44(12)
C5 C6 C1 110.16(11)
C5 O1 C6 61.21(9)
C7 N1 N2 108.24(9)
C7 N1 C4 117.97(10)
N2 N1 C4 111.34(10)
C8 N2 N1 107.45(10)
C8 N2 C1 118.85(11)
N1 N2 C1 111.49(9)
O3 C7 N1 126.49(11)
O3 C7 N3 127.48(11)
N1 C7 N3 106.01(10)
O2 C8 N2 126.18(12)
O2 C8 N3 127.09(12)
N2 C8 N3 106.68(10)
C8 N3 C7 110.57(10)
C8 N3 C9 124.43(10)
C7 N3 C9 124.83(10)
C10 C9 C14 121.36(12)
C10 C9 N3 118.91(11)
C14 C9 N3 119.72(11)
C9 C10 C11 118.64(12)
C12 C11 C10 120.52(13)
C13 C12 C11 120.11(13)
C12 C13 C14 120.33(13)
C13 C14 C9 119.02(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.502(2)
C1 N2 1.5093(16)
C1 C6 1.5320(18)
C2 C3 1.329(2)
C3 C4 1.501(2)
C4 N1 1.4997(16)
C4 C5 1.5331(18)
C5 O1 1.4341(17)
C5 C6 1.4625(19)
C6 O1 1.4383(16)
N1 C7 1.3882(16)
N1 N2 1.4444(14)
N2 C8 1.3894(16)
C7 O3 1.2087(15)
C7 N3 1.3981(15)
C8 O2 1.2098(15)
C8 N3 1.3954(16)
N3 C9 1.4329(15)
C9 C10 1.3862(18)
C9 C14 1.3872(18)
C10 C11 1.3906(18)
C11 C12 1.382(2)
C12 C13 1.381(2)
C13 C14 1.3868(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12966233
