#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/42/4504251.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_4504251
loop_
_publ_author_name
'Reddy, L. Sreenivas'
'Chandran, Sreekanth K.'
'George, Sumod'
'Babu, N. Jagadeesh'
'Nangia, Ashwini'
_publ_section_title
;
 Crystal Structures ofN-Aryl-N'-4-Nitrophenyl Ureas: Molecular Conformation
 and Weak Interactions Direct the Strong Hydrogen Bond Synthon
;
_journal_coden_ASTM              CGDEFU
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2675
_journal_page_last               2690
_journal_paper_doi               10.1021/cg070155j
_journal_volume                  7
_journal_year                    2007
_chemical_formula_moiety         'C13 H11 N3 O3, C3 H7 N O'
_chemical_formula_sum            'C16 H18 N4 O4'
_chemical_formula_weight         330.34
_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                 97.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4442(19)
_cell_length_b                   7.3883(15)
_cell_length_c                   23.863(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1649.9(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    0.0684
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4014
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             670
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1977
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1839
_refine_ls_wR_factor_ref         0.2408
_reflns_number_gt                1467
_reflns_number_total             3789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg070155j-file010.cif
_cod_data_source_block           5.8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

data name '_atom_site_symmetry_multiplicit' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        1650.0(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4504251
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
O1 O 0.2592(3) 0.8106(4) 0.45843(11) 0.0760(9) Uani 1 1 d .
C11 C 0.4187(4) 1.0670(5) 0.66201(15) 0.0522(9) Uani 1 1 d .
C8 C 0.2341(4) 0.9164(5) 0.57494(14) 0.0532(9) Uani 1 1 d .
N2 N 0.1349(3) 0.8395(5) 0.53425(13) 0.0638(9) Uani 1 1 d .
H2A H 0.0531 0.8163 0.5446 0.077 Uiso 1 1 calc R
N3 N 0.5153(4) 1.1447(5) 0.70864(15) 0.0692(10) Uani 1 1 d .
C7 C 0.1488(4) 0.7946(5) 0.47910(17) 0.0596(10) Uani 1 1 d .
O2 O 0.6354(3) 1.1888(5) 0.70036(13) 0.0944(11) Uani 1 1 d .
C10 C 0.4583(4) 1.0619(6) 0.60878(16) 0.0566(10) Uani 1 1 d .
N4 N 0.3165(3) 0.3381(5) 0.40389(15) 0.0651(9) Uani 1 1 d .
O4 O 0.1545(3) 0.2644(5) 0.46174(13) 0.0957(11) Uani 1 1 d .
C12 C 0.2891(4) 1.0013(6) 0.67321(17) 0.0606(11) Uani 1 1 d .
C13 C 0.1973(4) 0.9271(6) 0.62957(15) 0.0610(11) Uani 1 1 d .
H13A H 0.1091 0.8832 0.6366 0.073 Uiso 1 1 calc R
N1 N 0.0251(3) 0.7296(5) 0.45169(13) 0.0634(9) Uani 1 1 d .
H1A H -0.0439 0.7219 0.4717 0.076 Uiso 1 1 calc R
C9 C 0.3652(4) 0.9875(6) 0.56515(17) 0.0591(11) Uani 1 1 d .
O3 O 0.4736(4) 1.1616(6) 0.75454(13) 0.1070(13) Uani 1 1 d .
C1 C -0.0079(4) 0.6725(5) 0.39532(17) 0.0576(10) Uani 1 1 d .
C6 C -0.1355(5) 0.5824(6) 0.38080(17) 0.0693(12) Uani 1 1 d .
H6A H -0.1929 0.5576 0.4086 0.083 Uiso 1 1 calc R
C2 C 0.0775(4) 0.7051(6) 0.35357(17) 0.0655(11) Uani 1 1 d .
H2B H 0.1647 0.7639 0.3625 0.079 Uiso 1 1 calc R
C3 C 0.0335(6) 0.6505(7) 0.2992(2) 0.0758(13) Uani 1 1 d .
C16 C 0.2657(7) 0.3417(8) 0.4510(2) 0.1003(17) Uani 1 1 d .
H16A H 0.3165 0.4083 0.4802 0.120 Uiso 1 1 calc R
C5 C -0.1801(5) 0.5280(6) 0.3256(2) 0.0796(13) Uani 1 1 d .
H5A H -0.2671 0.4691 0.3162 0.096 Uiso 1 1 calc R
C4 C -0.0930(6) 0.5631(7) 0.2850(2) 0.0818(15) Uani 1 1 d .
C15 C 0.2347(7) 0.2423(8) 0.3567(2) 0.1140(19) Uani 1 1 d .
H15A H 0.1547 0.1827 0.3696 0.171 Uiso 1 1 calc R
H15B H 0.2947 0.1540 0.3421 0.171 Uiso 1 1 calc R
H15C H 0.2009 0.3271 0.3275 0.171 Uiso 1 1 calc R
C14 C 0.4384(5) 0.4333(8) 0.3909(3) 0.119(2) Uani 1 1 d .
H14A H 0.4852 0.4908 0.4244 0.179 Uiso 1 1 calc R
H14B H 0.4093 0.5235 0.3627 0.179 Uiso 1 1 calc R
H14C H 0.5031 0.3501 0.3767 0.179 Uiso 1 1 calc R
H10 H 0.545(4) 1.110(5) 0.6040(13) 0.049(10) Uiso 1 1 d .
H3 H 0.090(4) 0.664(5) 0.2747(16) 0.057(12) Uiso 1 1 d .
H9 H 0.390(3) 0.985(4) 0.5279(14) 0.045(9) Uiso 1 1 d .
H4 H -0.119(4) 0.523(6) 0.2474(19) 0.081(13) Uiso 1 1 d .
H12 H 0.261(3) 0.999(5) 0.7119(14) 0.057(10) Uiso 1 1 d .
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
C10 C11 C12 122.0(4)
C10 C11 N3 119.8(4)
C12 C11 N3 118.2(3)
N2 C8 C9 124.9(3)
N2 C8 C13 116.8(3)
C9 C8 C13 118.3(4)
C8 N2 C7 129.0(3)
O3 N3 O2 122.5(4)
O3 N3 C11 118.8(4)
O2 N3 C11 118.7(4)
O1 C7 N1 124.8(4)
O1 C7 N2 124.0(4)
N1 C7 N2 111.2(3)
C11 C10 C9 118.9(4)
C16 N4 C14 126.3(5)
C16 N4 C15 117.7(5)
C14 N4 C15 115.6(4)
C13 C12 C11 118.7(4)
C12 C13 C8 121.3(4)
C7 N1 C1 129.7(3)
C10 C9 C8 120.8(4)
C6 C1 C2 118.5(4)
C6 C1 N1 117.4(4)
C2 C1 N1 124.1(4)
C1 C6 C5 121.5(4)
C3 C2 C1 119.9(4)
C4 C3 C2 121.4(5)
O4 C16 N4 126.4(6)
C4 C5 C6 118.7(4)
C3 C4 C5 120.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.218(4)
C11 C10 1.372(5)
C11 C12 1.376(5)
C11 N3 1.458(5)
C8 N2 1.377(5)
C8 C9 1.394(5)
C8 C13 1.396(5)
N2 C7 1.380(5)
N3 O3 1.219(4)
N3 O2 1.221(4)
C7 N1 1.348(5)
C10 C9 1.383(5)
N4 C16 1.282(6)
N4 C14 1.419(5)
N4 C15 1.459(6)
O4 C16 1.251(6)
C12 C13 1.376(5)
N1 C1 1.404(5)
C1 C6 1.379(5)
C1 C2 1.385(5)
C6 C5 1.388(6)
C2 C3 1.368(6)
C3 C4 1.361(7)
C5 C4 1.377(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145471
