#------------------------------------------------------------------------------
#$Date: 2022-09-09 03:13:59 +0200 (Fri 09 de Sep de 2022) $
#$Revision: 277746 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/54/7245470.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_7245470
loop_
_publ_author_name
'Zhang, Yan'
'Long, Zhiwu'
'Yan, Longjia'
'Liu, Li'
'Yang, Lan'
'Le, Yi'
_publ_section_title
;
 Discovery of 4-nitro-3-phenylisoxazole derivatives as potent
 antibacterial agents derived from the studies of [3 + 2] cycloaddition
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              25633
_journal_page_last               25638
_journal_paper_doi               10.1039/D2RA05009A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C9 H5 F N2 O3'
_chemical_formula_weight         208.15
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_update_record
;
2021-12-21 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.850(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.3580(17)
_cell_length_b                   5.6716(8)
_cell_length_c                   8.2983(11)
_cell_measurement_reflns_used    897
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.727
_cell_measurement_theta_min      3.312
_cell_volume                     862.06(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  '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  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4040
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0869
_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)+(0.1360P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2481
_reflns_number_gt                948
_reflns_number_total             1488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ra05009a2.cif
_cod_data_source_block           210806b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7245470
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43354(19) -0.2879(8) 0.5405(5) 0.1258(16) Uani 1 1 d . . .
N1 N 0.1827(2) -0.3048(7) 0.8019(5) 0.0583(11) Uani 1 1 d . . .
N2 N 0.11970(19) 0.2060(6) 0.5749(4) 0.0492(10) Uani 1 1 d . . .
O1 O 0.10483(17) -0.3153(6) 0.7999(4) 0.0668(11) Uani 1 1 d . . .
O2 O 0.17296(17) 0.3053(6) 0.5280(4) 0.0655(10) Uani 1 1 d . . .
O3 O 0.05728(17) 0.2734(6) 0.5441(4) 0.0719(11) Uani 1 1 d . . .
C1 C 0.0768(2) -0.1322(9) 0.7209(5) 0.0572(12) Uani 1 1 d . . .
H1 H 0.0272 -0.0997 0.7034 0.069 Uiso 1 1 calc R . .
C2 C 0.13085(19) -0.0008(7) 0.6702(4) 0.0409(10) Uani 1 1 d . . .
C3 C 0.1972(2) -0.1140(8) 0.7226(5) 0.0469(11) Uani 1 1 d . . .
C4 C 0.2744(2) -0.0502(7) 0.7028(5) 0.0470(11) Uani 1 1 d . . .
C5 C 0.3184(2) -0.2054(8) 0.6256(5) 0.0572(12) Uani 1 1 d . . .
H5 H 0.2998 -0.3461 0.5827 0.069 Uiso 1 1 calc R . .
C6 C 0.3902(3) -0.1465(10) 0.6140(6) 0.0670(14) Uani 1 1 d . . .
C7 C 0.4197(2) 0.0541(11) 0.6739(6) 0.0733(16) Uani 1 1 d . . .
H7 H 0.4686 0.0895 0.6627 0.088 Uiso 1 1 calc R . .
C8 C 0.3754(3) 0.2067(10) 0.7528(6) 0.0704(15) Uani 1 1 d . . .
H8 H 0.3949 0.3450 0.7978 0.085 Uiso 1 1 calc R . .
C9 C 0.3026(2) 0.1557(8) 0.7654(5) 0.0581(13) Uani 1 1 d . . .
H9 H 0.2729 0.2610 0.8162 0.070 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.090(2) 0.156(4) 0.134(4) -0.029(3) 0.030(2) 0.031(2)
N1 0.060(2) 0.059(3) 0.055(2) 0.0115(19) -0.0003(17) -0.0038(18)
N2 0.050(2) 0.055(2) 0.042(2) 0.0005(17) 0.0038(16) 0.0021(17)
O1 0.066(2) 0.066(2) 0.068(2) 0.0149(17) 0.0055(16) -0.0153(16)
O2 0.064(2) 0.073(2) 0.060(2) 0.0202(16) 0.0074(15) -0.0033(16)
O3 0.0481(18) 0.088(3) 0.079(3) 0.0122(19) -0.0054(15) 0.0188(16)
C1 0.051(3) 0.071(3) 0.050(3) 0.002(2) 0.006(2) -0.007(2)
C2 0.045(2) 0.046(2) 0.0326(19) 0.0004(18) 0.0039(15) -0.0025(17)
C3 0.052(2) 0.053(3) 0.035(2) -0.0046(19) 0.0038(17) -0.0038(19)
C4 0.050(2) 0.053(3) 0.037(2) 0.0051(19) -0.0014(17) -0.0017(19)
C5 0.057(3) 0.064(3) 0.051(3) -0.007(2) 0.003(2) 0.013(2)
C6 0.051(3) 0.097(4) 0.054(3) 0.001(3) 0.008(2) 0.023(3)
C7 0.045(3) 0.108(5) 0.066(3) 0.014(3) 0.001(2) -0.003(3)
C8 0.061(3) 0.084(4) 0.066(3) 0.004(3) 0.001(2) -0.003(3)
C9 0.055(3) 0.060(3) 0.059(3) -0.004(2) 0.004(2) 0.001(2)
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 O1 105.5(3) . . ?
O2 N2 O3 123.6(4) . . ?
O2 N2 C2 118.2(3) . . ?
O3 N2 C2 118.3(4) . . ?
C1 O1 N1 109.3(3) . . ?
O1 C1 C2 108.9(4) . . ?
O1 C1 H1 125.6 . . ?
C2 C1 H1 125.6 . . ?
C1 C2 C3 107.0(4) . . ?
C1 C2 N2 123.7(4) . . ?
C3 C2 N2 129.2(3) . . ?
N1 C3 C2 109.3(3) . . ?
N1 C3 C4 119.2(4) . . ?
C2 C3 C4 131.5(4) . . ?
C9 C4 C5 120.1(4) . . ?
C9 C4 C3 120.6(4) . . ?
C5 C4 C3 119.3(4) . . ?
C6 C5 C4 118.3(4) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
F1 C6 C7 116.7(5) . . ?
F1 C6 C5 120.1(5) . . ?
C7 C6 C5 123.2(4) . . ?
C6 C7 C8 118.0(5) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
C9 C8 C7 120.6(5) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C4 C9 C8 119.8(4) . . ?
C4 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.309(6) . ?
N1 C3 1.303(5) . ?
N1 O1 1.429(5) . ?
N2 O2 1.215(4) . ?
N2 O3 1.219(4) . ?
N2 C2 1.422(5) . ?
O1 C1 1.314(6) . ?
C1 C2 1.332(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.419(5) . ?
C3 C4 1.482(5) . ?
C4 C9 1.366(6) . ?
C4 C5 1.381(6) . ?
C5 C6 1.369(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.342(8) . ?
C7 C8 1.383(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 O1 C1 -0.2(5) . . . . ?
N1 O1 C1 C2 0.0(5) . . . . ?
O1 C1 C2 C3 0.1(5) . . . . ?
O1 C1 C2 N2 177.3(4) . . . . ?
O2 N2 C2 C1 -176.1(4) . . . . ?
O3 N2 C2 C1 3.6(6) . . . . ?
O2 N2 C2 C3 0.5(6) . . . . ?
O3 N2 C2 C3 -179.9(4) . . . . ?
O1 N1 C3 C2 0.3(4) . . . . ?
O1 N1 C3 C4 179.7(3) . . . . ?
C1 C2 C3 N1 -0.3(5) . . . . ?
N2 C2 C3 N1 -177.2(4) . . . . ?
C1 C2 C3 C4 -179.6(4) . . . . ?
N2 C2 C3 C4 3.4(7) . . . . ?
N1 C3 C4 C9 -118.2(5) . . . . ?
C2 C3 C4 C9 61.2(6) . . . . ?
N1 C3 C4 C5 59.3(5) . . . . ?
C2 C3 C4 C5 -121.3(5) . . . . ?
C9 C4 C5 C6 -0.1(6) . . . . ?
C3 C4 C5 C6 -177.6(4) . . . . ?
C4 C5 C6 F1 -179.4(5) . . . . ?
C4 C5 C6 C7 0.0(7) . . . . ?
F1 C6 C7 C8 -179.8(5) . . . . ?
C5 C6 C7 C8 0.8(8) . . . . ?
C6 C7 C8 C9 -1.6(8) . . . . ?
C5 C4 C9 C8 -0.7(7) . . . . ?
C3 C4 C9 C8 176.8(4) . . . . ?
C7 C8 C9 C4 1.6(7) . . . . ?
