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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102785.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_8102785
loop_
_publ_author_name
'Janina Karolak-Wojciechowska'
'Ma»gorzata Szczesio'
'Tuba Ertan-Bolelli'
'Esin Aki'
'Ismail Yalçin'
_publ_section_title
;
 Crystal structure of 4-fluoro-N-(2-hydroxy-4-nitrophenyl)benzamide,
 C13H9FN2O4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              533
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C13 H9 F N2 O4'
_chemical_formula_weight         276.22
_chemical_name_systematic
; 
4-fluoro-N-(2-hydroxy-4-nitrophenyl)benzamide
;
_space_group_IT_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
_audit_update_record
;
2010-05-10 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.254(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3477(7)
_cell_length_b                   7.7697(9)
_cell_length_c                   21.295(3)
_cell_measurement_reflns_used    6004
_cell_measurement_temperature    298
_cell_measurement_theta_max      35.9965
_cell_measurement_theta_min      1.9323
_cell_volume                     1199.9(2)
_computing_cell_refinement       'CrysAlis RED [5]'
_computing_data_collection       'CrysAlis CCD [5]'
_computing_data_reduction        'CrysAlis RED [5]'
_computing_molecular_graphics    'SHELXTL [5] and Mercury [7]'
_computing_publication_material  'PLATON [8]'
_computing_structure_refinement  'SHELXTL [6]'
_computing_structure_solution    'SHELXTL [6]'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Kuma KM-4 CCD'
_diffrn_measurement_method       ω
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13469
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISMATIC
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0308
_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)+(0.0564P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                1588
_reflns_number_total             2118
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3089.cff
_cod_data_source_block           publication_text
_cod_database_code               8102785
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
C1 C -0.02960(16) 0.61250(16) 0.41899(6) 0.0346(3) Uani 1 1 d . . .
O2 O -0.13961(11) 0.66268(13) 0.45321(4) 0.0478(3) Uani 1 1 d . . .
N3 N 0.15159(13) 0.64665(13) 0.43413(5) 0.0375(3) Uani 1 1 d . . .
H3 H 0.2196 0.6100 0.4076 0.045 Uiso 1 1 calc R . .
C11 C -0.08945(16) 0.51446(16) 0.35956(6) 0.0348(3) Uani 1 1 d . . .
C12 C -0.27271(18) 0.52417(19) 0.33133(7) 0.0486(4) Uani 1 1 d . . .
H12 H -0.3537 0.5925 0.3497 0.058 Uiso 1 1 calc R . .
C13 C -0.3368(2) 0.4343(2) 0.27652(7) 0.0577(4) Uani 1 1 d . . .
H13 H -0.4599 0.4413 0.2578 0.069 Uiso 1 1 calc R . .
C14 C -0.2163(2) 0.3353(2) 0.25046(7) 0.0511(4) Uani 1 1 d . . .
F14 F -0.28087(13) 0.24697(13) 0.19644(4) 0.0793(3) Uani 1 1 d . . .
C15 C -0.0344(2) 0.32219(19) 0.27576(7) 0.0515(4) Uani 1 1 d . . .
H15 H 0.0452 0.2545 0.2564 0.062 Uiso 1 1 calc R . .
C16 C 0.02836(18) 0.41197(16) 0.33075(7) 0.0434(4) Uani 1 1 d . . .
H16 H 0.1519 0.4038 0.3489 0.052 Uiso 1 1 calc R . .
C31 C 0.24429(16) 0.73416(15) 0.48749(6) 0.0333(3) Uani 1 1 d . . .
C32 C 0.16057(17) 0.81996(16) 0.53186(6) 0.0371(3) Uani 1 1 d . . .
H32 H 0.0327 0.8239 0.5279 0.044 Uiso 1 1 calc R . .
C33 C 0.26959(17) 0.89966(15) 0.58219(6) 0.0376(3) Uani 1 1 d . . .
N33 N 0.17702(17) 0.98807(14) 0.62859(6) 0.0476(3) Uani 1 1 d . . .
O33 O 0.00833(15) 0.99345(13) 0.61987(5) 0.0595(3) Uani 1 1 d . . .
O34 O 0.27211(16) 1.05496(15) 0.67453(6) 0.0733(4) Uani 1 1 d . . .
C34 C 0.45883(18) 0.89864(17) 0.58972(7) 0.0434(4) Uani 1 1 d . . .
H34 H 0.5290 0.9534 0.6242 0.052 Uiso 1 1 calc R . .
C35 C 0.54245(17) 0.81426(18) 0.54477(6) 0.0433(4) Uani 1 1 d . . .
H35 H 0.6704 0.8127 0.5488 0.052 Uiso 1 1 calc R . .
C36 C 0.43750(16) 0.73265(16) 0.49411(6) 0.0355(3) Uani 1 1 d . . .
O36 O 0.50589(11) 0.64925(12) 0.44779(4) 0.0470(3) Uani 1 1 d . . .
H36 H 0.6257 0.6552 0.4520 0.070 Uiso 1 1 d 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'
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
O2 C1 N3 120.85(11) . . ?
O2 C1 C11 122.25(11) . . ?
N3 C1 C11 116.90(11) . . ?
C1 N3 C31 128.51(11) . . ?
C12 C11 C16 118.07(12) . . ?
C12 C11 C1 118.47(11) . . ?
C16 C11 C1 123.46(11) . . ?
C13 C12 C11 121.08(13) . . ?
C14 C13 C12 118.52(14) . . ?
C13 C14 F14 118.08(13) . . ?
C13 C14 C15 122.94(13) . . ?
F14 C14 C15 118.97(14) . . ?
C14 C15 C16 118.14(13) . . ?
C15 C16 C11 121.23(13) . . ?
C32 C31 N3 125.25(11) . . ?
C32 C31 C36 119.37(12) . . ?
N3 C31 C36 115.38(11) . . ?
C33 C32 C31 118.85(11) . . ?
C34 C33 C32 122.63(12) . . ?
C34 C33 N33 119.81(12) . . ?
C32 C33 N33 117.55(11) . . ?
O34 N33 O33 122.75(12) . . ?
O34 N33 C33 118.26(12) . . ?
O33 N33 C33 118.98(11) . . ?
C33 C34 C35 118.42(12) . . ?
C36 C35 C34 120.38(12) . . ?
O36 C36 C35 124.70(11) . . ?
O36 C36 C31 114.96(11) . . ?
C35 C36 C31 120.33(12) . . ?
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
C1 O2 1.2353(14) . ?
C1 N3 1.3449(15) . ?
C1 C11 1.4820(17) . ?
N3 C31 1.4031(16) . ?
C11 C12 1.3856(17) . ?
C11 C16 1.3895(17) . ?
C12 C13 1.377(2) . ?
C13 C14 1.357(2) . ?
C14 F14 1.3579(16) . ?
C14 C15 1.362(2) . ?
C15 C16 1.3772(19) . ?
C31 C32 1.3794(18) . ?
C31 C36 1.4040(17) . ?
C32 C33 1.3776(18) . ?
C33 C34 1.3738(18) . ?
C33 N33 1.4584(17) . ?
N33 O34 1.2230(15) . ?
N33 O33 1.2242(14) . ?
C34 C35 1.3830(19) . ?
C35 C36 1.3759(18) . ?
C36 O36 1.3435(15) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2906568
2 PubChem 3673746
