#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235099.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_2235099
loop_
_publ_author_name
'Yoon, Yeong Keng'
'Manogaran, Elumalai'
'Ali, Mohamed Ashraf'
'Arshad, Suhana'
'Razak, Ibrahim Abdul'
_publ_section_title
;
 Ethyl 4-anilino-3-nitrobenzoate
;
_journal_coeditor_code           IS5128
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1684
_journal_paper_doi               10.1107/S1600536812019903
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H14 N2 O4'
_chemical_formula_moiety         'C15 H14 N2 O4'
_chemical_formula_sum            'C15 H14 N2 O4'
_chemical_formula_weight         286.28
_chemical_name_systematic
;
Ethyl 4-anilino-3-nitrobenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 120.2440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6464(2)
_cell_length_b                   9.9178(2)
_cell_length_c                   14.7885(2)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      31.43
_cell_measurement_theta_min      2.85
_cell_volume                     1348.96(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω 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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17988
_diffrn_reflns_theta_full        31.92
_diffrn_reflns_theta_max         31.92
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.9647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         4639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0467
_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)+(0.0561P)²+0.2709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1244
_reflns_number_gt                3276
_reflns_number_total             4639
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is5128.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235099
_cod_database_fobs_code          2235099
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_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.28632(10) -0.12818(8) 0.76247(7) 0.01976(19) Uani d . 1 1
O O2 0.46453(10) 0.00161(9) 0.76921(7) 0.0212(2) Uani d . 1 1
O O3 0.66947(10) 0.34436(10) 1.03221(8) 0.0273(2) Uani d . 1 1
O O4 0.55970(10) 0.42674(9) 1.10945(8) 0.0228(2) Uani d . 1 1
N N1 0.33488(11) 0.29963(10) 1.09858(8) 0.0181(2) Uani d . 1 1
N N2 0.56820(11) 0.34349(10) 1.05006(8) 0.0184(2) Uani d . 1 1
C C1 0.46344(13) 0.16060(11) 0.92632(9) 0.0165(2) Uani d . 1 1
H H1A 0.5353 0.1764 0.9095 0.020 Uiso calc R 1 1
C C2 0.45671(12) 0.24143(11) 1.00074(9) 0.0154(2) Uani d . 1 1
C C3 0.34771(13) 0.22195(11) 1.02854(9) 0.0153(2) Uani d . 1 1
C C4 0.24935(13) 0.11392(12) 0.97700(9) 0.0169(2) Uani d . 1 1
H H4A 0.1767 0.0968 0.9929 0.020 Uiso calc R 1 1
C C5 0.25813(13) 0.03416(12) 0.90452(10) 0.0173(2) Uani d . 1 1
H H5A 0.1924 -0.0362 0.8730 0.021 Uiso calc R 1 1
C C6 0.36523(13) 0.05748(11) 0.87723(9) 0.0161(2) Uani d . 1 1
C C7 0.37913(13) -0.02319(12) 0.79882(10) 0.0173(2) Uani d . 1 1
C C8 0.29118(15) -0.20792(13) 0.68146(11) 0.0239(3) Uani d . 1 1
H H8A 0.3826 -0.2563 0.7107 0.029 Uiso calc R 1 1
H H8B 0.2825 -0.1497 0.6259 0.029 Uiso calc R 1 1
C C9 0.16782(18) -0.30447(14) 0.63980(12) 0.0324(3) Uani d . 1 1
H H9A 0.1677 -0.3582 0.5858 0.049 Uiso calc R 1 1
H H9B 0.0780 -0.2555 0.6114 0.049 Uiso calc R 1 1
H H9C 0.1780 -0.3620 0.6953 0.049 Uiso calc R 1 1
C C10 0.23046(13) 0.27774(12) 1.13077(10) 0.0175(2) Uani d . 1 1
C C11 0.11792(14) 0.37011(13) 1.10012(11) 0.0227(3) Uani d . 1 1
H H11A 0.1090 0.4418 1.0567 0.027 Uiso calc R 1 1
C C12 0.01887(15) 0.35537(14) 1.13428(12) 0.0281(3) Uani d . 1 1
H H12A -0.0559 0.4176 1.1143 0.034 Uiso calc R 1 1
C C13 0.03126(15) 0.24804(14) 1.19810(12) 0.0287(3) Uani d . 1 1
H H13A -0.0359 0.2374 1.2202 0.034 Uiso calc R 1 1
C C14 0.14412(16) 0.15626(14) 1.22907(12) 0.0269(3) Uani d . 1 1
H H14A 0.1528 0.0846 1.2724 0.032 Uiso calc R 1 1
C C15 0.24447(15) 0.17090(12) 1.19555(11) 0.0218(3) Uani d . 1 1
H H15A 0.3202 0.1095 1.2165 0.026 Uiso calc R 1 1
H H1N1 0.3899(19) 0.3693(16) 1.1227(13) 0.030(4) Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
C7 O1 C8 115.13(9)
C3 N1 C10 124.35(10)
C3 N1 H1N1 117.8(11)
C10 N1 H1N1 117.8(11)
O3 N2 O4 122.02(11)
O3 N2 C2 118.75(10)
O4 N2 C2 119.23(9)
C6 C1 C2 121.06(10)
C6 C1 H1A 119.5
C2 C1 H1A 119.5
C1 C2 C3 121.55(11)
C1 C2 N2 116.46(10)
C3 C2 N2 121.97(10)
N1 C3 C4 120.59(10)
N1 C3 C2 123.68(11)
C4 C3 C2 115.72(10)
C5 C4 C3 122.11(10)
C5 C4 H4A 118.9
C3 C4 H4A 118.9
C4 C5 C6 120.86(11)
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C1 C6 C5 118.69(10)
C1 C6 C7 117.78(10)
C5 C6 C7 123.53(11)
O2 C7 O1 122.94(11)
O2 C7 C6 124.18(11)
O1 C7 C6 112.88(9)
O1 C8 C9 107.49(10)
O1 C8 H8A 110.2
C9 C8 H8A 110.2
O1 C8 H8B 110.2
C9 C8 H8B 110.2
H8A C8 H8B 108.5
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C15 C10 C11 120.29(11)
C15 C10 N1 121.04(11)
C11 C10 N1 118.58(11)
C12 C11 C10 120.00(13)
C12 C11 H11A 120.0
C10 C11 H11A 120.0
C13 C12 C11 120.03(13)
C13 C12 H12A 120.0
C11 C12 H12A 120.0
C12 C13 C14 119.90(11)
C12 C13 H13A 120.0
C14 C13 H13A 120.0
C13 C14 C15 120.36(13)
C13 C14 H14A 119.8
C15 C14 H14A 119.8
C10 C15 C14 119.41(12)
C10 C15 H15A 120.3
C14 C15 H15A 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.3470(15)
O1 C8 1.4582(14)
O2 C7 1.2165(13)
O3 N2 1.2325(12)
O4 N2 1.2415(13)
N1 C3 1.3518(14)
N1 C10 1.4293(14)
N1 H1N1 0.858(17)
N2 C2 1.4468(15)
C1 C6 1.3789(17)
C1 C2 1.3923(15)
C1 H1A 0.9300
C2 C3 1.4262(15)
C3 C4 1.4218(16)
C4 C5 1.3727(16)
C4 H4A 0.9300
C5 C6 1.4071(15)
C5 H5A 0.9300
C6 C7 1.4764(16)
C8 C9 1.485(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C15 1.3852(17)
C10 C11 1.3904(17)
C11 C12 1.3875(17)
C11 H11A 0.9300
C12 C13 1.384(2)
C12 H12A 0.9300
C13 C14 1.388(2)
C13 H13A 0.9300
C14 C15 1.3935(17)
C14 H14A 0.9300
C15 H15A 0.9300
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
_geom_hbond_publ_flag
N1 H1N1 O4 . 0.859(18) 2.00(2) 2.6375(17) 130.6(17) yes
N1 H1N1 O2 4_566 0.858(17) 2.288(16) 2.9411(14) 133.0(14) yes
C15 H15A O2 3_657 0.9300 2.4500 3.342(2) 160.00 yes
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
C6 C1 C2 C3 -0.58(18)
C6 C1 C2 N2 177.85(11)
O3 N2 C2 C1 -7.34(16)
O4 N2 C2 C1 173.15(11)
O3 N2 C2 C3 171.07(11)
O4 N2 C2 C3 -8.44(17)
C10 N1 C3 C4 3.33(18)
C10 N1 C3 C2 -177.07(11)
C1 C2 C3 N1 -178.51(11)
N2 C2 C3 N1 3.15(18)
C1 C2 C3 C4 1.12(17)
N2 C2 C3 C4 -177.22(10)
N1 C3 C4 C5 179.17(12)
C2 C3 C4 C5 -0.47(17)
C3 C4 C5 C6 -0.72(19)
C2 C1 C6 C5 -0.65(18)
C2 C1 C6 C7 179.67(11)
C4 C5 C6 C1 1.29(18)
C4 C5 C6 C7 -179.04(11)
C8 O1 C7 O2 -2.29(17)
C8 O1 C7 C6 177.49(10)
C1 C6 C7 O2 -5.67(18)
C5 C6 C7 O2 174.66(12)
C1 C6 C7 O1 174.56(10)
C5 C6 C7 O1 -5.11(17)
C7 O1 C8 C9 -171.43(11)
C3 N1 C10 C15 72.36(17)
C3 N1 C10 C11 -110.92(14)
C15 C10 C11 C12 -0.1(2)
N1 C10 C11 C12 -176.86(12)
C10 C11 C12 C13 -0.6(2)
C11 C12 C13 C14 0.9(2)
C12 C13 C14 C15 -0.5(2)
C11 C10 C15 C14 0.49(19)
N1 C10 C15 C14 177.15(12)
C13 C14 C15 C10 -0.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741365
2 PubChem 12459631
