#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/50/1545034.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1545034
loop_
_publ_author_name
'Essaghouani, Abdelhanine'
'Boulhaoua, Mohammed'
'El Ouasif, Latifa'
'Sebbar, Nada Kheira'
'Essassi, El Mokhtar'
'Mague, Joel T.'
_publ_section_title
;
 3-Phenylisoxazolin-5-one: a redetermination
;
_journal_coeditor_code           HB4110
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x170032
_journal_paper_doi               10.1107/S2414314617000323
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          'C9 H7 N O2'
_chemical_formula_moiety         'C9 H7 N O2'
_chemical_formula_sum            'C9 H7 N O2'
_chemical_formula_weight         161.16
_chemical_name_systematic
;
3-Phenylisoxazolin-5-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.106(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9869(6)
_cell_length_b                   5.3008(3)
_cell_length_c                   13.9874(9)
_cell_measurement_reflns_used    4379
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.06
_cell_measurement_theta_min      5.59
_cell_volume                     739.39(8)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT  (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5465
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         72.056
_diffrn_reflns_theta_min         5.309
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.139
_refine_ls_extinction_coef       0.0097(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0338
_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)+(0.0441P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                1282
_reflns_number_total             1433
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4110sup1.cif
_cod_data_source_block           I
_cod_database_code               1545034
_cod_database_fobs_code          1545034
_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   0.854
_shelx_estimated_absorpt_t_max   0.953
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 0.72988(8) 0.35740(17) 0.61102(6) 0.0291(3) Uani d 1
O O2 0.83139(9) 0.67872(19) 0.68908(7) 0.0345(3) Uani d 1
N N1 0.59421(10) 0.2725(2) 0.59036(8) 0.0276(3) Uani d 1
C C1 0.51416(12) 0.4307(2) 0.62725(8) 0.0219(3) Uani d 1
C C2 0.58547(12) 0.6434(2) 0.67731(9) 0.0254(3) Uani d 1
H H2A 0.5637(15) 0.811(3) 0.6485(11) 0.033(4) Uiso d 1
H H2B 0.5708(16) 0.650(3) 0.7461(12) 0.036(4) Uiso d 1
C C3 0.72877(12) 0.5762(2) 0.66339(9) 0.0260(3) Uani d 1
C C4 0.36809(12) 0.3949(2) 0.61691(8) 0.0223(3) Uani d 1
C C5 0.31305(13) 0.1913(2) 0.56468(9) 0.0270(3) Uani d 1
H H5 0.3730(16) 0.070(3) 0.5343(11) 0.037(4) Uiso d 1
C C6 0.17523(13) 0.1648(3) 0.55302(9) 0.0308(3) Uani d 1
H H6 0.1396(18) 0.020(4) 0.5152(13) 0.050(5) Uiso d 1
C C7 0.09063(13) 0.3393(3) 0.59296(9) 0.0297(3) Uani d 1
H H7 -0.0084(17) 0.321(3) 0.5830(11) 0.035(4) Uiso d 1
C C8 0.14499(13) 0.5399(3) 0.64548(9) 0.0293(3) Uani d 1
H H8 0.0864(18) 0.661(3) 0.6743(12) 0.043(4) Uiso d 1
C C9 0.28324(12) 0.5680(2) 0.65752(9) 0.0258(3) Uani d 1
H H9 0.3184(16) 0.708(3) 0.6934(11) 0.037(4) Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 O1 N1 109.63(8)
C1 N1 O1 108.30(10)
N1 C1 C4 120.76(11)
N1 C1 C2 113.00(10)
C4 C1 C2 126.23(10)
C1 C2 C3 101.24(10)
C1 C2 H2A 113.4(9)
C3 C2 H2A 110.5(9)
C1 C2 H2B 113.2(9)
C3 C2 H2B 109.3(9)
H2A C2 H2B 109.0(13)
O2 C3 O1 120.81(11)
O2 C3 C2 131.38(12)
O1 C3 C2 107.81(10)
C9 C4 C5 119.43(11)
C9 C4 C1 119.84(11)
C5 C4 C1 120.71(11)
C6 C5 C4 119.98(12)
C6 C5 H5 120.2(9)
C4 C5 H5 119.8(9)
C5 C6 C7 120.49(12)
C5 C6 H6 118.0(11)
C7 C6 H6 121.5(11)
C8 C7 C6 119.61(12)
C8 C7 H7 120.3(9)
C6 C7 H7 120.1(9)
C7 C8 C9 120.30(12)
C7 C8 H8 120.1(10)
C9 C8 H8 119.6(10)
C8 C9 C4 120.18(12)
C8 C9 H9 118.9(9)
C4 C9 H9 120.9(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.3720(16)
O1 N1 1.4420(13)
O2 C3 1.1980(16)
N1 C1 1.2857(16)
C1 C4 1.4704(16)
C1 C2 1.4881(17)
C2 C3 1.4977(16)
C2 H2A 0.995(16)
C2 H2B 0.981(16)
C4 C9 1.3913(17)
C4 C5 1.3990(17)
C5 C6 1.3843(18)
C5 H5 0.991(17)
C6 C7 1.390(2)
C6 H6 0.988(19)
C7 C8 1.386(2)
C7 H7 0.995(16)
C8 C9 1.3899(17)
C8 H8 0.972(18)
C9 H9 0.952(17)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2A N1 1_565 0.995(16) 2.602(16) 3.5525(17) 160.0(12)
C5 H5 N1 3_656 0.991(17) 2.55(2) 3.438(2) 149.0(10)
C8 H8 O2 1_455 0.972(18) 2.57(2) 3.306(2) 133.0(10)
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
C3 O1 N1 C1 0.43(13)
O1 N1 C1 C4 179.36(9)
O1 N1 C1 C2 0.20(14)
N1 C1 C2 C3 -0.68(14)
C4 C1 C2 C3 -179.79(11)
N1 O1 C3 O2 179.42(11)
N1 O1 C3 C2 -0.86(13)
C1 C2 C3 O2 -179.41(14)
C1 C2 C3 O1 0.91(12)
N1 C1 C4 C9 179.89(11)
C2 C1 C4 C9 -1.07(18)
N1 C1 C4 C5 -1.60(17)
C2 C1 C4 C5 177.44(11)
C9 C4 C5 C6 0.62(18)
C1 C4 C5 C6 -177.90(11)
C4 C5 C6 C7 -0.07(19)
C5 C6 C7 C8 -0.5(2)
C6 C7 C8 C9 0.56(19)
C7 C8 C9 C4 -0.01(19)
C5 C4 C9 C8 -0.58(18)
C1 C4 C9 C8 177.95(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 70641
