#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:32:52 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270490 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060983.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_7060983 loop_ _publ_author_name 'Laha, Joydev K.' 'Singh, Neha' 'Hunjan, Mandeep Kaur' _publ_section_title ; Synthesis of unsymmetrical urea from aryl- or pyridyl carboxamides and aminopyridines using PhI(OAc)2via in situ formation of aryl- or pyridyl isocyanates ; _journal_issue 40 _journal_name_full 'New Journal of Chemistry' _journal_page_first 18815 _journal_page_last 18823 _journal_paper_doi 10.1039/D1NJ03160K _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C13 H10 F3 N3 O' _chemical_formula_sum 'C13 H10 F3 N3 O' _chemical_formula_weight 281.24 _chemical_name_systematic 1-(pyridin-2-yl)-3-(3-(trifluoromethyl)phenyl)urea _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2021-06-06 deposited with the CCDC. 2021-09-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 115.755(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.7883(11) _cell_length_b 5.8469(5) _cell_length_c 16.4107(16) _cell_measurement_reflns_used 12105 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.66 _cell_measurement_theta_min 2.5 _cell_volume 1278.00(19) _computing_cell_refinement 'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)' _computing_data_collection 'APEX2 (Bruker, 2014)' _computing_data_reduction 'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)' _computing_molecular_graphics 'Ortep, Platon, mercury' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.233 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Bruker D8 Venture PHOTON 100 CMOS' _diffrn_measurement_method 'phi and omega scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_unetI/netI 0.0484 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.977 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 12105 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.329 _diffrn_reflns_theta_min 2.504 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6519 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_meas 1.42 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.270 _refine_diff_density_max 0.551 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 3115 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.025 _refine_ls_R_factor_all 0.1065 _refine_ls_R_factor_gt 0.0864 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1370P)^2^+0.8201P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2426 _refine_ls_wR_factor_ref 0.2591 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2317 _reflns_number_total 3115 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03160k2.cif _cod_data_source_block shelx _cod_depositor_comments 'Adding full bibliography for 7060983.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7060983 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.961 _shelx_estimated_absorpt_t_max 0.967 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL Mono_a.res in P2(1)/c CELL 0.71073 14.7883 5.8469 16.4107 90.000 115.755 90.000 ZERR 4.00 0.0011 0.0005 0.0016 0.000 0.003 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O F UNIT 52 40 12 4 12 MERG 2 FMAP 2 PLAN 25 ACTA SIZE 0.270 0.300 0.320 L.S. 4 TEMP 20.00 WGHT 0.137000 0.820100 FVAR 1.24088 O1 4 0.905768 0.408520 0.895782 11.00000 0.04515 0.05296 = 0.04782 -0.01240 0.00252 0.01320 N3 3 1.123194 -0.091464 0.940897 11.00000 0.04095 0.04706 = 0.05252 -0.00055 0.01804 0.00507 N2 3 0.939406 0.075513 0.841545 11.00000 0.03686 0.05146 = 0.04500 -0.01072 0.00783 0.00921 AFIX 43 H2 2 0.987751 -0.015650 0.848159 11.00000 -1.20000 AFIX 0 F1 5 0.586273 0.388005 0.711721 11.00000 0.06809 0.14183 = 0.11422 -0.04172 0.01107 0.04141 N1 3 1.059053 0.251903 0.968952 11.00000 0.04017 0.04615 = 0.04684 -0.01093 0.00799 0.00470 AFIX 43 H1 2 1.072877 0.367393 1.004816 11.00000 -1.20000 AFIX 0 F2 5 0.547603 0.328906 0.577883 11.00000 0.11137 0.15905 = 0.08673 0.04561 0.02234 0.06910 C3 1 0.759897 0.157671 0.747352 11.00000 0.04131 0.04503 = 0.03871 -0.00445 0.01202 0.00054 AFIX 43 H3 2 0.763497 0.295561 0.776858 11.00000 -1.20000 AFIX 0 C10 1 1.228988 0.148225 1.064346 11.00000 0.04139 0.05989 = 0.04445 0.00120 0.01148 -0.00188 AFIX 43 H10 2 1.236912 0.280629 1.098187 11.00000 -1.20000 AFIX 0 F3 5 0.501083 0.102903 0.648332 11.00000 0.05535 0.09947 = 0.32759 0.01744 0.08072 -0.00301 C4 1 0.844917 0.023141 0.771044 11.00000 0.04025 0.04291 = 0.03425 -0.00171 0.01358 -0.00146 C2 1 0.669451 0.084147 0.679143 11.00000 0.04023 0.05287 = 0.04234 0.00236 0.01189 -0.00318 C9 1 1.137621 0.096969 0.990584 11.00000 0.03616 0.04660 = 0.04263 0.00257 0.01557 0.00175 C5 1 0.837934 -0.179770 0.724057 11.00000 0.05187 0.04438 = 0.04865 -0.00444 0.02007 0.00377 AFIX 43 H5 2 0.894883 -0.269474 0.739027 11.00000 -1.20000 AFIX 0 C11 1 1.306484 -0.004188 1.084897 11.00000 0.03506 0.08112 = 0.05281 0.01398 0.00961 0.00490 AFIX 43 H11 2 1.368540 0.025550 1.132915 11.00000 -1.20000 AFIX 0 C13 1 1.200798 -0.237138 0.964053 11.00000 0.05060 0.05043 = 0.06525 0.00565 0.02833 0.01125 AFIX 43 H13 2 1.191315 -0.369839 0.930059 11.00000 -1.20000 AFIX 0 C7 1 0.663332 -0.117637 0.633047 11.00000 0.05239 0.05610 = 0.05178 -0.00736 0.01136 -0.01388 AFIX 43 H7 2 0.602421 -0.164034 0.586963 11.00000 -1.20000 AFIX 0 C6 1 0.747995 -0.249195 0.655858 11.00000 0.06515 0.04808 = 0.05587 -0.01513 0.02113 -0.01028 AFIX 43 H6 2 0.744438 -0.385113 0.625171 11.00000 -1.20000 AFIX 0 C12 1 1.292687 -0.201453 1.034579 11.00000 0.04569 0.06497 = 0.07218 0.01876 0.02671 0.01798 AFIX 43 H12 2 1.344413 -0.306724 1.048327 11.00000 -1.20000 AFIX 0 C8 1 0.962830 0.252579 0.899999 11.00000 0.03770 0.04428 = 0.03659 -0.00212 0.01084 0.00360 C1 1 0.577314 0.221586 0.655471 11.00000 0.03867 0.07189 = 0.06061 0.00072 0.00740 0.00171 HKLF 4 REM Mono_a.res in P2(1)/c REM R1 = 0.0864 for 2317 Fo > 4sig(Fo) and 0.1065 for all 3115 data REM 181 parameters refined using 0 restraints END WGHT 0.1370 0.8201 REM Highest difference peak 0.551, deepest hole -0.391, 1-sigma level 0.058 Q1 1 0.5386 0.1984 0.7149 11.00000 0.05 0.55 Q2 1 0.5798 0.4184 0.6479 11.00000 0.05 0.52 Q3 1 0.5110 0.1413 0.5750 11.00000 0.05 0.51 Q4 1 0.9684 0.4580 0.8984 11.00000 0.05 0.25 Q5 1 0.6283 0.1555 0.6697 11.00000 0.05 0.20 Q6 1 0.8898 0.0600 0.8078 11.00000 0.05 0.20 Q7 1 0.9504 0.5686 0.8988 11.00000 0.05 0.19 Q8 1 1.1843 0.1131 1.0308 11.00000 0.05 0.19 Q9 1 1.0780 -0.0773 0.8906 11.00000 0.05 0.19 Q10 1 0.6663 -0.0206 0.6731 11.00000 0.05 0.18 Q11 1 0.8516 0.3828 0.8604 11.00000 0.05 0.17 Q12 1 1.2312 0.4259 1.0808 11.00000 0.05 0.17 Q13 1 1.1615 -0.1718 0.9447 11.00000 0.05 0.17 Q14 1 0.7098 0.1196 0.7086 11.00000 0.05 0.17 Q15 1 1.1239 0.3217 1.1082 11.00000 0.05 0.17 Q16 1 1.1877 -0.4615 0.9590 11.00000 0.05 0.16 Q17 1 1.0910 0.1722 0.9662 11.00000 0.05 0.16 Q18 1 0.9387 0.1117 0.8934 11.00000 0.05 0.16 Q19 1 1.2523 0.0396 1.0827 11.00000 0.05 0.16 Q20 1 0.7989 0.0665 0.7689 11.00000 0.05 0.16 Q21 1 1.2946 -0.1524 1.0757 11.00000 0.05 0.15 Q22 1 1.1456 0.0518 0.9410 11.00000 0.05 0.15 Q23 1 0.8691 0.5196 0.9040 11.00000 0.05 0.15 Q24 1 0.9847 -0.0902 0.8753 11.00000 0.05 0.15 Q25 1 1.1908 0.3635 1.1102 11.00000 0.05 0.14 ; _shelx_res_checksum 37875 loop_ _space_group_symop_operation_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.90577(14) 0.4085(3) 0.89578(13) 0.0550(6) Uani 1 1 d . . . . . N3 N 1.12319(16) -0.0915(4) 0.94090(16) 0.0477(6) Uani 1 1 d . . . . . N2 N 0.93941(15) 0.0755(4) 0.84154(15) 0.0480(6) Uani 1 1 d . . . . . H2 H 0.9878 -0.0157 0.8482 0.058 Uiso 1 1 calc R U . . . F1 F 0.58627(18) 0.3880(5) 0.7117(2) 0.1182(11) Uani 1 1 d . . . . . N1 N 1.05905(15) 0.2519(4) 0.96895(15) 0.0483(6) Uani 1 1 d . . . . . H1 H 1.0729 0.3674 1.0048 0.058 Uiso 1 1 calc R U . . . F2 F 0.5476(2) 0.3289(6) 0.57788(19) 0.1264(11) Uani 1 1 d . . . . . C3 C 0.75990(18) 0.1577(5) 0.74735(17) 0.0436(6) Uani 1 1 d . . . . . H3 H 0.7635 0.2956 0.7769 0.052 Uiso 1 1 calc R U . . . C10 C 1.2290(2) 0.1482(5) 1.06435(19) 0.0511(7) Uani 1 1 d . . . . . H10 H 1.2369 0.2806 1.0982 0.061 Uiso 1 1 calc R U . . . F3 F 0.50108(19) 0.1029(5) 0.6483(4) 0.1617(18) Uani 1 1 d . . . . . C4 C 0.84492(18) 0.0231(4) 0.77104(16) 0.0401(6) Uani 1 1 d . . . . . C2 C 0.66945(19) 0.0841(5) 0.67914(18) 0.0473(6) Uani 1 1 d . . . . . C9 C 1.13762(18) 0.0970(4) 0.99058(17) 0.0423(6) Uani 1 1 d . . . . . C5 C 0.8379(2) -0.1798(5) 0.72406(19) 0.0489(6) Uani 1 1 d . . . . . H5 H 0.8949 -0.2695 0.7390 0.059 Uiso 1 1 calc R U . . . C11 C 1.3065(2) -0.0042(6) 1.0849(2) 0.0597(8) Uani 1 1 d . . . . . H11 H 1.3685 0.0256 1.1329 0.072 Uiso 1 1 calc R U . . . C13 C 1.2008(2) -0.2371(5) 0.9641(2) 0.0543(7) Uani 1 1 d . . . . . H13 H 1.1913 -0.3698 0.9301 0.065 Uiso 1 1 calc R U . . . C7 C 0.6633(2) -0.1176(5) 0.6330(2) 0.0575(7) Uani 1 1 d . . . . . H7 H 0.6024 -0.1640 0.5870 0.069 Uiso 1 1 calc R U . . . C6 C 0.7480(2) -0.2492(5) 0.6559(2) 0.0582(8) Uani 1 1 d . . . . . H6 H 0.7444 -0.3851 0.6252 0.070 Uiso 1 1 calc R U . . . C12 C 1.2927(2) -0.2015(6) 1.0346(2) 0.0606(8) Uani 1 1 d . . . . . H12 H 1.3444 -0.3067 1.0483 0.073 Uiso 1 1 calc R U . . . C8 C 0.96283(18) 0.2526(4) 0.90000(16) 0.0414(6) Uani 1 1 d . . . . . C1 C 0.5773(2) 0.2216(6) 0.6555(2) 0.0621(8) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0452(10) 0.0530(11) 0.0478(11) -0.0124(9) 0.0025(8) 0.0132(8) N3 0.0409(11) 0.0471(12) 0.0525(13) -0.0005(10) 0.0180(10) 0.0051(9) N2 0.0369(10) 0.0515(13) 0.0450(12) -0.0107(10) 0.0078(9) 0.0092(9) F1 0.0681(14) 0.142(2) 0.114(2) -0.0417(18) 0.0111(13) 0.0414(15) N1 0.0402(11) 0.0462(12) 0.0468(12) -0.0109(10) 0.0080(9) 0.0047(9) F2 0.111(2) 0.159(3) 0.0867(18) 0.0456(18) 0.0223(15) 0.069(2) C3 0.0413(12) 0.0450(14) 0.0387(13) -0.0044(10) 0.0120(10) 0.0005(10) C10 0.0414(13) 0.0599(17) 0.0444(14) 0.0012(12) 0.0115(11) -0.0019(12) F3 0.0553(13) 0.099(2) 0.328(6) 0.017(3) 0.081(2) -0.0030(13) C4 0.0403(12) 0.0429(13) 0.0342(12) -0.0017(10) 0.0136(10) -0.0015(10) C2 0.0402(13) 0.0529(15) 0.0423(14) 0.0024(11) 0.0119(11) -0.0032(11) C9 0.0362(11) 0.0466(14) 0.0426(13) 0.0026(11) 0.0156(10) 0.0017(10) C5 0.0519(14) 0.0444(14) 0.0487(15) -0.0044(12) 0.0201(12) 0.0038(12) C11 0.0351(12) 0.081(2) 0.0528(17) 0.0140(16) 0.0096(12) 0.0049(13) C13 0.0506(15) 0.0504(16) 0.0652(18) 0.0057(13) 0.0283(14) 0.0112(12) C7 0.0524(15) 0.0561(17) 0.0518(16) -0.0074(13) 0.0114(13) -0.0139(13) C6 0.0651(18) 0.0481(16) 0.0559(17) -0.0151(13) 0.0211(15) -0.0103(13) C12 0.0457(15) 0.0650(19) 0.072(2) 0.0188(16) 0.0267(14) 0.0180(14) C8 0.0377(12) 0.0443(13) 0.0366(12) -0.0021(10) 0.0108(10) 0.0036(10) C1 0.0387(14) 0.072(2) 0.0606(18) 0.0007(16) 0.0074(13) 0.0017(13) 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 C9 N3 C13 117.5(2) . . ? C8 N2 C4 127.4(2) . . ? C8 N1 C9 131.3(2) . . ? C2 C3 C4 119.3(2) . . ? C11 C10 C9 117.5(3) . . ? C3 C4 C5 119.1(2) . . ? C3 C4 N2 124.2(2) . . ? C5 C4 N2 116.6(2) . . ? C7 C2 C3 121.1(3) . . ? C7 C2 C1 119.0(3) . . ? C3 C2 C1 119.9(3) . . ? N3 C9 N1 119.2(2) . . ? N3 C9 C10 123.0(2) . . ? N1 C9 C10 117.8(2) . . ? C6 C5 C4 120.9(3) . . ? C10 C11 C12 120.3(3) . . ? N3 C13 C12 123.8(3) . . ? C6 C7 C2 119.5(3) . . ? C7 C6 C5 120.0(3) . . ? C13 C12 C11 117.9(3) . . ? O1 C8 N2 125.0(2) . . ? O1 C8 N1 119.2(2) . . ? N2 C8 N1 115.8(2) . . ? F3 C1 F1 106.4(3) . . ? F3 C1 F2 105.0(3) . . ? F1 C1 F2 102.6(3) . . ? F3 C1 C2 113.7(3) . . ? F1 C1 C2 114.8(2) . . ? F2 C1 C2 113.3(3) . . ? 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 O1 C8 1.224(3) . ? N3 C9 1.332(3) . ? N3 C13 1.345(3) . ? N2 C8 1.350(3) . ? N2 C4 1.407(3) . ? F1 C1 1.308(4) . ? N1 C8 1.381(3) . ? N1 C9 1.392(3) . ? F2 C1 1.312(4) . ? C3 C2 1.388(3) . ? C3 C4 1.388(3) . ? C10 C11 1.373(4) . ? C10 C9 1.400(4) . ? F3 C1 1.285(4) . ? C4 C5 1.394(4) . ? C2 C7 1.383(4) . ? C2 C1 1.481(4) . ? C5 C6 1.376(4) . ? C11 C12 1.381(5) . ? C13 C12 1.365(5) . ? C7 C6 1.376(4) . ?