#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206997.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_2206997 loop_ _publ_author_name 'Ya-Juan Zhao' 'Xin-Hua Li' _publ_section_title ; 4-Nitrophenol--urea (1/1) ; _journal_coeditor_code JH6018 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3366 _journal_page_last o3367 _journal_paper_doi 10.1107/S1600536805029442 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C6 H5 N O3, C H4 N2 O' _chemical_formula_moiety 'C6 H5 N O3, C H4 N2 O' _chemical_formula_sum 'C7 H9 N3 O4' _chemical_formula_weight 199.17 _chemical_name_systematic ; 4-Nitrophenol--carbamide (1/1) ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 98.634(4) _cell_angle_beta 92.415(5) _cell_angle_gamma 99.326(4) _cell_formula_units_Z 2 _cell_length_a 3.7619(9) _cell_length_b 10.230(2) _cell_length_c 11.810(3) _cell_measurement_reflns_used 1561 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.09 _cell_measurement_theta_min 1.75 _cell_volume 442.38(18) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker APEX area-detector' _diffrn_measurement_method '600 frames, \d \w = 0.3\%' _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 0.0131 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2362 _diffrn_reflns_theta_full 25.09 _diffrn_reflns_theta_max 25.09 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.175 _refine_diff_density_min -0.182 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1561 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0610 _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/[\s^2^(Fo^2^)+(0.0564P)^2^+0.2445P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1293 _refine_ls_wR_factor_ref 0.1412 _reflns_number_gt 1234 _reflns_number_total 1561 _reflns_threshold_expression I>2\s(I) _cod_data_source_file jh6018.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Integration' changed to 'integration' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Integration' changed to 'integration' 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 ; _cod_database_code 2206997 _cod_database_fobs_code 2206997 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _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_type_symbol O1 0.4143(7) 0.1179(2) -0.12760(18) 0.0757(8) Uani d . 1 O O2 0.7330(7) 0.3127(2) -0.12460(18) 0.0707(7) Uani d . 1 O O3 0.3260(6) 0.37109(19) 0.38223(15) 0.0505(6) Uani d . 1 O H3 0.2059 0.3091 0.4076 0.061 Uiso d R 1 H N1 0.5483(7) 0.2295(3) -0.0767(2) 0.0493(6) Uani d . 1 N C1 0.4884(7) 0.2644(2) 0.0432(2) 0.0360(6) Uani d . 1 C C2 0.6306(7) 0.3919(3) 0.1001(2) 0.0388(6) Uani d . 1 C H2 0.7615 0.4546 0.0616 0.047 Uiso calc R 1 H C3 0.5751(7) 0.4240(3) 0.2140(2) 0.0388(6) Uani d . 1 C H3A 0.6720 0.5089 0.2532 0.047 Uiso calc R 1 H C4 0.3762(7) 0.3316(3) 0.2715(2) 0.0358(6) Uani d . 1 C C5 0.2390(7) 0.2037(3) 0.2130(2) 0.0395(7) Uani d . 1 C H5 0.1080 0.1409 0.2514 0.047 Uiso calc R 1 H C6 0.2952(7) 0.1699(3) 0.0998(2) 0.0392(7) Uani d . 1 C H6 0.2047 0.0841 0.0610 0.047 Uiso calc R 1 H O4 0.9669(6) 0.17135(19) 0.46670(16) 0.0518(6) Uani d . 1 O N2 0.7830(7) 0.3079(2) 0.6120(2) 0.0509(7) Uani d . 1 N H2B 0.8154 0.3743 0.5746 0.061 Uiso d R 1 H H2C 0.7054 0.3184 0.6797 0.061 Uiso d R 1 H N3 0.8076(7) 0.0900(2) 0.6259(2) 0.0573(7) Uani d . 1 N H3B 0.8550 0.0124 0.5985 0.069 Uiso d R 1 H H3C 0.7297 0.1034 0.6934 0.069 Uiso d R 1 H C7 0.8543(7) 0.1886(3) 0.5643(2) 0.0380(6) Uani d . 1 C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.112(2) 0.0670(16) 0.0417(13) 0.0110(14) 0.0081(13) -0.0089(12) O2 0.0967(19) 0.0771(16) 0.0446(13) 0.0157(14) 0.0300(13) 0.0218(12) O3 0.0675(14) 0.0494(12) 0.0339(11) 0.0056(10) 0.0131(9) 0.0059(9) N1 0.0631(17) 0.0554(16) 0.0336(13) 0.0213(13) 0.0081(12) 0.0069(12) C1 0.0389(15) 0.0420(15) 0.0302(14) 0.0143(12) 0.0036(11) 0.0076(11) C2 0.0382(15) 0.0392(15) 0.0425(16) 0.0075(12) 0.0110(12) 0.0149(12) C3 0.0373(15) 0.0343(14) 0.0435(16) 0.0036(11) 0.0038(12) 0.0044(12) C4 0.0355(15) 0.0407(14) 0.0333(14) 0.0101(11) 0.0042(11) 0.0086(11) C5 0.0401(16) 0.0388(14) 0.0401(16) 0.0000(12) 0.0045(12) 0.0145(12) C6 0.0448(16) 0.0327(14) 0.0385(16) 0.0041(12) 0.0001(12) 0.0038(11) O4 0.0741(15) 0.0476(12) 0.0349(11) 0.0090(10) 0.0216(10) 0.0068(9) N2 0.0702(18) 0.0444(14) 0.0405(14) 0.0140(12) 0.0172(12) 0.0062(11) N3 0.092(2) 0.0481(14) 0.0390(14) 0.0217(14) 0.0275(13) 0.0131(11) C7 0.0409(16) 0.0424(15) 0.0290(14) 0.0050(12) 0.0044(11) 0.0023(12) 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 _geom_angle_publ_flag C4 O3 H3 109.4 yes O1 N1 O2 122.0(2) yes O1 N1 C1 119.0(2) yes O2 N1 C1 119.0(3) yes C6 C1 C2 121.1(2) yes C6 C1 N1 119.7(2) yes C2 C1 N1 119.2(2) yes C3 C2 C1 118.9(2) yes C3 C2 H2 120.5 ? C1 C2 H2 120.5 ? C2 C3 C4 120.8(2) yes C2 C3 H3A 119.6 ? C4 C3 H3A 119.6 ? O3 C4 C3 117.5(2) yes O3 C4 C5 123.1(2) yes C3 C4 C5 119.4(2) yes C6 C5 C4 120.4(2) yes C6 C5 H5 119.8 ? C4 C5 H5 119.8 ? C5 C6 C1 119.4(2) yes C5 C6 H6 120.3 ? C1 C6 H6 120.3 ? C7 N2 H2B 119.6 ? C7 N2 H2C 120.4 ? H2B N2 H2C 120.0 ? C7 N3 H3B 120.0 ? C7 N3 H3C 120.0 ? H3B N3 H3C 120.0 ? O4 C7 N3 121.0(2) yes O4 C7 N2 121.4(3) yes N3 C7 N2 117.6(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N1 1.225(3) yes O2 N1 1.230(3) yes O3 C4 1.341(3) yes O3 H3 0.8200 ? N1 C1 1.444(3) yes C1 C6 1.385(4) yes C1 C2 1.386(4) yes C2 C3 1.368(4) yes C2 H2 0.9300 ? C3 C4 1.386(4) yes C3 H3A 0.9300 ? C4 C5 1.390(4) yes C5 C6 1.365(4) yes C5 H5 0.9300 ? C6 H6 0.9300 ? O4 C7 1.243(3) yes N2 C7 1.339(3) yes N2 H2B 0.8600 ? N2 H2C 0.8600 ? N3 C7 1.323(3) yes N3 H3B 0.8600 ? N3 H3C 0.8601 ? 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 N3 H3C O1 1_556 0.86 2.46 3.316(3) 171 N3 H3B O4 2_756 0.86 2.14 3.000(3) 174 N2 H2C O2 1_556 0.86 2.32 3.118(3) 155 O3 H3 O4 1_455 0.82 1.79 2.613(3) 177 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 O1 N1 C1 C6 2.8(4) O2 N1 C1 C6 -177.0(3) O1 N1 C1 C2 -178.1(3) O2 N1 C1 C2 2.0(4) C6 C1 C2 C3 -0.5(4) N1 C1 C2 C3 -179.5(2) C1 C2 C3 C4 -0.8(4) C2 C3 C4 O3 -178.5(2) C2 C3 C4 C5 1.5(4) O3 C4 C5 C6 179.2(2) C3 C4 C5 C6 -0.8(4) C4 C5 C6 C1 -0.5(4) C2 C1 C6 C5 1.1(4) N1 C1 C6 C5 -179.8(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21128784 2 PubChem 139068455