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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/55/7125557.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_7125557
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            'C16 H15 N3 O3'
_chemical_formula_weight         297.31
_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_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                   13.5339(10)
_cell_length_b                   11.3119(8)
_cell_length_c                   9.3316(7)
_cell_measurement_reflns_used    6119
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.65
_cell_volume                     1428.61(18)
_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 0.996
_diffrn_measured_fraction_theta_max 0.943
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7985
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(15)
_refine_ls_extinction_coef       0.0034(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0388
_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)+(0.0511P)²+0.3105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                1606
_reflns_number_total             1767
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b205079j.txt
_cod_data_source_block           btg50
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7125557
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
C1 C 0.86832(17) 0.5150(2) 0.5529(2) 0.0218(5) Uani 1 1 d .
H1 H 0.8544 0.4289 0.5389 0.026 Uiso 1 1 calc R
C2 C 0.97944(18) 0.5440(2) 0.5354(3) 0.0237(5) Uani 1 1 d .
C3 C 0.99644(17) 0.6705(2) 0.5560(3) 0.0255(5) Uani 1 1 d .
C4 C 0.89789(18) 0.7350(2) 0.5868(3) 0.0239(5) Uani 1 1 d .
H4 H 0.9073 0.8222 0.5980 0.029 Uiso 1 1 calc R
C5 C 0.80667(18) 0.5912(2) 0.4561(3) 0.0262(5) Uani 1 1 d .
H5 H 0.7610 0.5602 0.3886 0.031 Uiso 1 1 calc R
C6 C 0.82207(18) 0.7058(2) 0.4739(3) 0.0262(5) Uani 1 1 d .
H6 H 0.7883 0.7646 0.4202 0.031 Uiso 1 1 calc R
C7 C 1.0511(2) 0.4469(3) 0.5711(3) 0.0369(7) Uani 1 1 d .
H7A H 1.1188 0.4772 0.5645 0.055 Uiso 1 1 calc R
H7B H 1.0426 0.3815 0.5034 0.055 Uiso 1 1 calc R
H7C H 1.0386 0.4187 0.6688 0.055 Uiso 1 1 calc R
C8 C 1.0871(2) 0.7231(3) 0.6207(4) 0.0420(8) Uani 1 1 d .
H8A H 1.0990 0.8013 0.5788 0.063 Uiso 1 1 calc R
H8B H 1.1438 0.6717 0.6013 0.063 Uiso 1 1 calc R
H8C H 1.0780 0.7309 0.7244 0.063 Uiso 1 1 calc R
C9 C 0.76355(17) 0.5244(2) 0.7764(3) 0.0207(5) Uani 1 1 d .
C10 C 0.79400(16) 0.7231(2) 0.8116(3) 0.0201(5) Uani 1 1 d .
C11 C 0.66205(16) 0.6304(2) 0.9624(3) 0.0209(5) Uani 1 1 d .
C12 C 0.56924(18) 0.5838(2) 0.9348(3) 0.0267(5) Uani 1 1 d .
H12 H 0.5558 0.5464 0.8458 0.032 Uiso 1 1 calc R
C13 C 0.4959(2) 0.5925(3) 1.0392(4) 0.0343(7) Uani 1 1 d .
H13 H 0.4323 0.5598 1.0218 0.041 Uiso 1 1 calc R
C14 C 0.5154(2) 0.6486(2) 1.1682(3) 0.0330(6) Uani 1 1 d .
H14 H 0.4650 0.6553 1.2386 0.040 Uiso 1 1 calc R
C15 C 0.6083(2) 0.6951(3) 1.1943(3) 0.0319(6) Uani 1 1 d .
H15 H 0.6214 0.7337 1.2827 0.038 Uiso 1 1 calc R
C16 C 0.68234(19) 0.6854(2) 1.0923(3) 0.0255(5) Uani 1 1 d .
H16 H 0.7464 0.7161 1.1110 0.031 Uiso 1 1 calc R
N1 N 0.84839(14) 0.55401(17) 0.7031(2) 0.0204(4) Uani 1 1 d .
N2 N 0.86681(14) 0.67763(17) 0.7238(2) 0.0207(4) Uani 1 1 d .
N3 N 0.73793(14) 0.62549(16) 0.8551(2) 0.0196(4) Uani 1 1 d .
O1 O 1.00433(13) 0.61893(16) 0.4152(2) 0.0278(4) Uani 1 1 d .
O2 O 0.72234(13) 0.42943(15) 0.7768(2) 0.0299(4) Uani 1 1 d .
O3 O 0.78268(13) 0.82525(15) 0.8458(2) 0.0276(4) Uani 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
N1 C1 C5 107.09(18)
N1 C1 C2 102.20(19)
C5 C1 C2 110.76(19)
O1 C2 C3 59.42(15)
O1 C2 C7 116.8(2)
C3 C2 C7 125.8(2)
O1 C2 C1 115.62(19)
C3 C2 C1 110.3(2)
C7 C2 C1 116.6(2)
O1 C3 C2 59.72(15)
O1 C3 C8 118.0(2)
C2 C3 C8 125.0(2)
O1 C3 C4 115.1(2)
C2 C3 C4 110.5(2)
C8 C3 C4 116.5(2)
N2 C4 C6 108.16(19)
N2 C4 C3 101.39(19)
C6 C4 C3 110.7(2)
C6 C5 C1 113.6(2)
C5 C6 C4 114.1(2)
O2 C9 N1 127.0(2)
O2 C9 N3 127.4(2)
N1 C9 N3 105.54(19)
O3 C10 N2 127.1(2)
O3 C10 N3 127.5(2)
N2 C10 N3 105.39(19)
C12 C11 C16 120.7(2)
C12 C11 N3 120.3(2)
C16 C11 N3 119.0(2)
C11 C12 C13 119.3(2)
C14 C13 C12 120.2(2)
C15 C14 C13 120.0(3)
C14 C15 C16 120.3(3)
C15 C16 C11 119.4(2)
C9 N1 N2 108.37(18)
C9 N1 C1 123.0(2)
N2 N1 C1 112.55(18)
C10 N2 N1 108.60(17)
C10 N2 C4 123.18(19)
N1 N2 C4 110.92(18)
C10 N3 C9 110.91(19)
C10 N3 C11 124.02(19)
C9 N3 C11 125.03(19)
C3 O1 C2 60.87(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.494(3)
C1 C5 1.502(3)
C1 C2 1.548(3)
C2 O1 1.446(3)
C2 C3 1.462(4)
C2 C7 1.503(4)
C3 O1 1.441(3)
C3 C8 1.491(4)
C3 C4 1.547(3)
C4 N2 1.494(3)
C4 C6 1.507(4)
C5 C6 1.323(4)
C9 O2 1.211(3)
C9 N1 1.378(3)
C9 N3 1.403(3)
C10 O3 1.209(3)
C10 N2 1.381(3)
C10 N3 1.400(3)
C11 C12 1.386(3)
C11 C16 1.390(4)
C11 N3 1.435(3)
C12 C13 1.394(4)
C13 C14 1.386(5)
C14 C15 1.384(4)
C15 C16 1.387(4)
N1 N2 1.434(3)
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 -125.0(2)
C5 C1 C2 O1 -11.2(3)
N1 C1 C2 C3 -60.1(2)
C5 C1 C2 C3 53.7(3)
N1 C1 C2 C7 92.0(2)
C5 C1 C2 C7 -154.2(2)
C7 C2 C3 O1 102.6(3)
C1 C2 C3 O1 -108.5(2)
O1 C2 C3 C8 -104.8(3)
C7 C2 C3 C8 -2.2(4)
C1 C2 C3 C8 146.7(3)
O1 C2 C3 C4 107.8(2)
C7 C2 C3 C4 -149.5(2)
C1 C2 C3 C4 -0.6(3)
O1 C3 C4 N2 127.5(2)
C2 C3 C4 N2 62.4(2)
C8 C3 C4 N2 -88.1(3)
O1 C3 C4 C6 12.9(3)
C2 C3 C4 C6 -52.2(3)
C8 C3 C4 C6 157.3(2)
N1 C1 C5 C6 55.5(3)
C2 C1 C5 C6 -55.2(3)
C1 C5 C6 C4 0.1(3)
N2 C4 C6 C5 -55.6(3)
C3 C4 C6 C5 54.7(3)
C16 C11 C12 C13 0.0(4)
N3 C11 C12 C13 -178.2(2)
C11 C12 C13 C14 0.9(4)
C12 C13 C14 C15 -0.8(4)
C13 C14 C15 C16 -0.2(4)
C14 C15 C16 C11 1.1(4)
C12 C11 C16 C15 -0.9(4)
N3 C11 C16 C15 177.3(2)
O2 C9 N1 N2 175.5(2)
N3 C9 N1 N2 -7.2(2)
O2 C9 N1 C1 41.3(4)
N3 C9 N1 C1 -141.4(2)
C5 C1 N1 C9 76.7(3)
C2 C1 N1 C9 -166.8(2)
C5 C1 N1 N2 -55.9(2)
C2 C1 N1 N2 60.6(2)
O3 C10 N2 N1 -175.7(2)
N3 C10 N2 N1 5.7(2)
O3 C10 N2 C4 -43.6(4)
N3 C10 N2 C4 137.8(2)
C9 N1 N2 C10 0.9(2)
C1 N1 N2 C10 140.29(19)
C9 N1 N2 C4 -137.4(2)
C1 N1 N2 C4 2.0(2)
C6 C4 N2 C10 -78.4(3)
C3 C4 N2 C10 165.1(2)
C6 C4 N2 N1 52.8(2)
C3 C4 N2 N1 -63.7(2)
O3 C10 N3 C9 170.9(2)
N2 C10 N3 C9 -10.5(3)
O3 C10 N3 C11 -7.0(4)
N2 C10 N3 C11 171.6(2)
O2 C9 N3 C10 -171.6(2)
N1 C9 N3 C10 11.1(3)
O2 C9 N3 C11 6.2(4)
N1 C9 N3 C11 -171.0(2)
C12 C11 N3 C10 129.5(2)
C16 C11 N3 C10 -48.7(3)
C12 C11 N3 C9 -48.1(3)
C16 C11 N3 C9 133.7(2)
C8 C3 O1 C2 116.2(3)
C4 C3 O1 C2 -100.0(2)
C7 C2 O1 C3 -117.6(3)
C1 C2 O1 C3 99.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 12966235
