#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/22/2232244.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_2232244
loop_
_publ_author_name
'Merzouki, Soraya'
'Mouats, Chabane'
'Bendeif, El-Eulmi'
'Pillet, Sebastien'
'Bouchouit, Karim'
_publ_section_title
;
 1-[3-(4-Nitrophenyl)propanoyl]urea acetic acid monosolvate
;
_journal_coeditor_code           FY2022
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2892
_journal_paper_doi               10.1107/S1600536811039729
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H11 N3 O4, C2 H4 O2'
_chemical_formula_moiety         'C10 H11 N3 O4, C2 H4 O2'
_chemical_formula_sum            'C12 H15 N3 O6'
_chemical_formula_weight         297.27
_chemical_name_systematic
;
1-[3-(4-Nitrophenyl)propanoyl]urea acetic acid monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.736(3)
_cell_angle_beta                 92.939(3)
_cell_angle_gamma                91.091(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4252(3)
_cell_length_b                   7.9601(3)
_cell_length_c                   11.4375(4)
_cell_measurement_reflns_used    4625
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      3.19
_cell_volume                     674.20(4)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia,
1997)
;
_computing_publication_material  'enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16680
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9539
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(ABSORB; DeTitta, 1985)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0406
_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)+(0.0556P)²+0.2344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                3563
_reflns_number_total             3913
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fy2022.cif
_cod_data_source_block           I
_cod_database_code               2232244
_cod_database_fobs_code          2232244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_symmetry_multiplicity
N N2 0.77505(12) 0.49422(11) 0.56957(8) 0.01868(18) Uani d 1 1
O O3 0.51190(10) 0.47679(9) 0.66343(7) 0.02065(17) Uani d 1 1
C C9 0.64971(13) 0.55423(12) 0.64495(8) 0.01614(18) Uani d 1 1
C C10 0.77604(14) 0.33654(13) 0.51251(9) 0.01820(19) Uani d 1 1
O O4 0.91036(11) 0.30011(10) 0.45541(7) 0.02409(18) Uani d 1 1
N N3 0.63746(13) 0.23181(11) 0.52143(8) 0.01982(18) Uani d 1 1
O O5 0.71569(11) 0.90282(10) 0.41754(7) 0.02333(17) Uani d 1 1
O O6 0.95760(12) 1.01068(11) 0.33799(8) 0.0291(2) Uani d 1 1
C C11 0.84078(14) 0.88799(13) 0.35312(9) 0.0189(2) Uani d 1 1
C C12 0.87300(17) 0.73163(14) 0.28067(10) 0.0242(2) Uani d 1 1
H H71 0.450(2) 0.7953(19) 0.7578(13) 0.025(4) Uiso d 1 1
H H81 0.820(2) 0.714(2) 0.7386(14) 0.029(4) Uiso d 1 1
H H6 0.865(2) 1.0680(19) 1.1039(14) 0.028(4) Uiso d 1 1
H H2 0.619(2) 1.350(2) 0.8551(15) 0.038(4) Uiso d 1 1
H H82 0.710(2) 0.8064(19) 0.6429(13) 0.026(4) Uiso d 1 1
H H5 0.763(2) 0.822(2) 0.9966(13) 0.029(4) Uiso d 1 1
H H72 0.556(2) 0.687(2) 0.8510(14) 0.029(4) Uiso d 1 1
H H3 0.524(2) 1.101(2) 0.7488(14) 0.029(4) Uiso d 1 1
H H9 0.871(2) 0.555(2) 0.5624(14) 0.030(4) Uiso d 1 1
H H10 0.545(2) 0.263(2) 0.5625(14) 0.029(4) Uiso d 1 1
H H11 0.646(2) 0.127(2) 0.4896(14) 0.033(4) Uiso d 1 1
H H121 0.832(2) 0.635(2) 0.3199(16) 0.041(5) Uiso d 1 1
H H 0.927(3) 1.101(3) 0.383(2) 0.064(6) Uiso d 1 1
H H122 0.999(3) 0.723(2) 0.2602(16) 0.047(5) Uiso d 1 1
H H123 0.802(3) 0.738(3) 0.207(2) 0.067(6) Uiso d 1 1
C C4 0.63442(13) 0.93684(12) 0.86240(9) 0.01726(19) Uani d 1 1
C C1 0.75280(14) 1.22675(12) 0.98721(9) 0.0184(2) Uani d 1 1
C C8 0.70192(14) 0.72292(12) 0.70362(9) 0.01779(19) Uani d 1 1
N N1 0.81408(14) 1.38040(12) 1.05424(9) 0.0242(2) Uani d 1 1
C C5 0.73579(15) 0.92833(13) 0.96774(9) 0.0193(2) Uani d 1 1
C C7 0.56967(15) 0.77809(13) 0.79493(9) 0.0203(2) Uani d 1 1
C C3 0.59529(15) 1.09439(14) 0.82046(9) 0.0218(2) Uani d 1 1
O O1 0.90310(14) 1.36682(12) 1.14622(9) 0.0386(2) Uani d 1 1
C C2 0.65298(16) 1.24075(13) 0.88280(10) 0.0221(2) Uani d 1 1
C C6 0.79598(15) 1.07320(13) 1.03125(9) 0.0195(2) Uani d 1 1
O O2 0.77247(18) 1.51546(11) 1.01607(10) 0.0464(3) Uani 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
C9 N2 C10 127.24(9)
C9 N2 H9 117.7(11)
C10 N2 H9 114.6(11)
O3 C9 N2 123.04(9)
O3 C9 C8 123.57(9)
N2 C9 C8 113.38(8)
O4 C10 N3 123.15(9)
O4 C10 N2 117.71(9)
N3 C10 N2 119.13(9)
C10 N3 H10 120.3(11)
C10 N3 H11 117.3(11)
H10 N3 H11 122.2(15)
C11 O6 H 107.8(14)
O5 C11 O6 123.10(10)
O5 C11 C12 123.45(10)
O6 C11 C12 113.42(9)
C11 C12 H121 109.7(11)
C11 C12 H122 112.0(11)
H121 C12 H122 112.5(15)
C11 C12 H123 107.4(13)
H121 C12 H123 108.7(17)
H122 C12 H123 106.3(17)
C5 C4 C3 118.86(9)
C5 C4 C7 120.31(9)
C3 C4 C7 120.83(10)
C6 C1 C2 122.52(9)
C6 C1 N1 118.62(9)
C2 C1 N1 118.86(9)
C9 C8 C7 112.08(8)
C9 C8 H81 107.3(10)
C7 C8 H81 110.8(10)
C9 C8 H82 108.7(9)
C7 C8 H82 110.8(9)
H81 C8 H82 106.8(13)
O2 N1 O1 123.29(10)
O2 N1 C1 118.30(10)
O1 N1 C1 118.41(9)
C6 C5 C4 121.10(9)
C6 C5 H5 119.4(10)
C4 C5 H5 119.4(10)
C4 C7 C8 111.51(8)
C4 C7 H71 109.6(9)
C8 C7 H71 110.7(9)
C4 C7 H72 108.9(9)
C8 C7 H72 109.1(9)
H71 C7 H72 106.8(13)
C2 C3 C4 121.03(10)
C2 C3 H3 119.5(10)
C4 C3 H3 119.4(10)
C1 C2 C3 118.28(10)
C1 C2 H2 121.2(10)
C3 C2 H2 120.5(10)
C1 C6 C5 118.21(10)
C1 C6 H6 120.4(9)
C5 C6 H6 121.4(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C9 1.3776(12)
N2 C10 1.3871(12)
N2 H9 0.866(17)
O3 C9 1.2175(13)
C9 C8 1.5070(13)
C10 O4 1.2510(12)
C10 N3 1.3230(14)
N3 H10 0.884(17)
N3 H11 0.898(18)
O5 C11 1.2189(13)
O6 C11 1.3174(13)
O6 H 0.90(2)
C11 C12 1.4920(14)
C12 H121 0.960(18)
C12 H122 0.98(2)
C12 H123 0.97(2)
C4 C5 1.3926(15)
C4 C3 1.3944(14)
C4 C7 1.5064(14)
C1 C6 1.3811(14)
C1 C2 1.3831(15)
C1 N1 1.4643(13)
C8 C7 1.5250(14)
C8 H81 0.950(16)
C8 H82 0.987(15)
N1 O2 1.2187(13)
N1 O1 1.2237(14)
C5 C6 1.3872(14)
C5 H5 0.942(16)
C7 H71 0.981(15)
C7 H72 1.000(16)
C3 C2 1.3854(15)
C3 H3 0.956(15)
C2 H2 0.977(17)
C6 H6 0.958(16)
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
O6 H O4 1_565 0.90(2) 1.76(2) 2.6492(12) 166(2)
N2 H9 O4 2_766 0.863(15) 1.998(15) 2.8611(12) 178.7(15)
N3 H10 O3 1_555 0.884(15) 2.036(16) 2.6892(12) 129.8(13)
N3 H10 O5 2_666 0.884(15) 2.349(15) 2.9434(13) 124.7(13)
N3 H11 O5 1_545 0.899(16) 2.017(16) 2.9050(12) 169.1(14)
C2 H2 O3 1_565 0.980(16) 2.550(17) 3.3434(14) 138.0(13)
C3 H3 O5 2_676 0.957(16) 2.536(15) 3.4793(13) 168.6(12)
C5 H5 O2 1_545 0.945(16) 2.463(16) 3.3724(14) 161.6(12)
C8 H81 O1 2_777 0.950(15) 2.496(15) 3.4266(15) 166.3(13)
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
C10 N2 C9 O3 -6.33(17)
C10 N2 C9 C8 172.56(9)
C9 N2 C10 O4 -173.81(10)
C9 N2 C10 N3 5.63(16)
O3 C9 C8 C7 4.31(14)
N2 C9 C8 C7 -174.57(9)
C6 C1 N1 O2 -178.56(11)
C2 C1 N1 O2 1.00(16)
C6 C1 N1 O1 0.81(15)
C2 C1 N1 O1 -179.63(11)
C3 C4 C5 C6 0.67(15)
C7 C4 C5 C6 -179.76(9)
C5 C4 C7 C8 -92.93(12)
C3 C4 C7 C8 86.63(12)
C9 C8 C7 C4 173.53(9)
C5 C4 C3 C2 -1.10(16)
C7 C4 C3 C2 179.33(10)
C6 C1 C2 C3 -0.24(17)
N1 C1 C2 C3 -179.77(10)
C4 C3 C2 C1 0.88(17)
C2 C1 C6 C5 -0.18(16)
N1 C1 C6 C5 179.36(9)
C4 C5 C6 C1 -0.04(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139082247
