#------------------------------------------------------------------------------ #$Date: 2019-11-11 20:42:04 +0200 (Mon, 11 Nov 2019) $ #$Revision: 227297 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035897.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_4035897 loop_ _publ_author_name 'Chaudhary, Priyanka' 'Gupta, Surabhi' 'Muniyappan, Nalluchamy' 'Sabiah, Shahulhameed' 'Kandasamy, Jeyakumar' _publ_section_title ; Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition. ; _journal_issue 1 _journal_name_full 'The Journal of organic chemistry' _journal_page_first 104 _journal_page_last 119 _journal_paper_doi 10.1021/acs.joc.8b02377 _journal_volume 84 _journal_year 2019 _chemical_formula_moiety 'C9 H7 Cl N2 O2' _chemical_formula_sum 'C9 H7 Cl N2 O2' _chemical_formula_weight 210.62 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2016-11-26 _audit_creation_method ; Olex2 1.2-ac2 (compiled 2012.03.27 svn.r2268, GUI svn.r4156) ; _cell_angle_alpha 112.463(10) _cell_angle_beta 95.209(9) _cell_angle_gamma 99.616(8) _cell_formula_units_Z 2 _cell_length_a 6.1027(5) _cell_length_b 8.5357(9) _cell_length_c 10.1750(11) _cell_measurement_reflns_used 1407 _cell_measurement_temperature 295 _cell_measurement_theta_max 28.9568 _cell_measurement_theta_min 3.7445 _cell_volume 475.92(9) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _diffrn_ambient_temperature 295 _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.9949 _diffrn_measured_fraction_theta_max 0.9487 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -71.00 -45.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 -37.0000 90.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -5.00 27.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 96.0000 -80.0000 32 #__ type_ start__ end____ width___ exp.time_ 3 omega -16.00 17.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 -99.0000 -180.0000 33 #__ type_ start__ end____ width___ exp.time_ 4 omega -83.00 -42.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 -178.0000 -150.0000 41 #__ type_ start__ end____ width___ exp.time_ 5 omega -37.00 44.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 57.0000 -180.0000 81 #__ type_ start__ end____ width___ exp.time_ 6 omega -13.00 17.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 -99.0000 60.0000 30 #__ type_ start__ end____ width___ exp.time_ 7 omega -37.00 -4.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 77.0000 60.0000 33 #__ type_ start__ end____ width___ exp.time_ 8 omega -55.00 -21.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 96.0000 -80.0000 34 #__ type_ start__ end____ width___ exp.time_ 9 omega -1.00 87.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.2147 57.0000 60.0000 88 #__ type_ start__ end____ width___ exp.time_ 10 omega 14.00 41.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.2147 -57.0000 -90.0000 27 #__ type_ start__ end____ width___ exp.time_ 11 omega -50.00 -14.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.2147 -57.0000 -90.0000 36 #__ type_ start__ end____ width___ exp.time_ 12 omega -2.00 88.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 19.2147 57.0000 -60.0000 90 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0053051000 _diffrn_orient_matrix_UB_12 0.0836338000 _diffrn_orient_matrix_UB_13 0.0500899000 _diffrn_orient_matrix_UB_21 0.0279281000 _diffrn_orient_matrix_UB_22 0.0351869000 _diffrn_orient_matrix_UB_23 -0.0507348000 _diffrn_orient_matrix_UB_31 -0.1161917000 _diffrn_orient_matrix_UB_32 -0.0161594000 _diffrn_orient_matrix_UB_33 -0.0278542000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_unetI/netI 0.0347 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5163 _diffrn_reflns_theta_full 29.02 _diffrn_reflns_theta_max 29.02 _diffrn_reflns_theta_min 3.75 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.374 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 216 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.167 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 131 _refine_ls_number_reflns 2216 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0423 _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^)+(0.0491P)^2^+0.0486P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1003 _refine_ls_wR_factor_ref 0.1128 _reflns_number_gt 1587 _reflns_number_total 2216 _reflns_threshold_expression >2sigma(I) _cod_data_source_file jo8b02377_si_001.cif _cod_data_source_block 4an _cod_original_cell_volume 475.92(8) _cod_database_code 4035897 _chemical_oxdiff_formula 'C9 H7 O2 N2 Cl' _chemical_oxdiff_usercomment 'YELLOWCOLOUR PLATE, 295K, 0.7 0.18 0.06' _reflns_odcompleteness_completeness 99.49 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' 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 Cl1 Cl 0.33824(8) 0.47455(7) 0.76486(7) 0.0706(2) Uani 1 1 d . O2 O 1.1047(3) 0.7204(2) 1.09871(15) 0.0671(4) Uani 1 1 d . O3 O 1.3294(2) 0.87921(19) 1.02549(14) 0.0589(4) Uani 1 1 d . N4 N 1.1960(3) 0.9363(2) 0.79910(17) 0.0440(4) Uani 1 1 d . N5 N 1.1444(3) 0.7871(2) 1.01345(15) 0.0435(4) Uani 1 1 d . C6 C 0.7655(3) 0.6481(2) 0.88744(19) 0.0424(4) Uani 1 1 d . H6 H 0.7494 0.5995 0.9546 0.051 Uiso 1 1 calc R C7 C 1.0025(3) 0.8325(2) 0.79583(17) 0.0354(4) Uani 1 1 d . C8 C 1.2299(3) 0.8914(3) 0.5499(2) 0.0503(5) Uani 1 1 d . C9 C 0.8125(3) 0.7933(2) 0.68852(19) 0.0435(4) Uani 1 1 d . H9 H 0.8237 0.8418 0.6209 0.052 Uiso 1 1 calc R C10 C 1.2310(3) 1.0160(2) 0.6974(2) 0.0504(5) Uani 1 1 d . H10A H 1.3745 1.0993 0.7315 0.061 Uiso 1 1 calc R H10B H 1.1137 1.0793 0.6952 0.061 Uiso 1 1 calc R C11 C 0.9682(3) 0.7568(2) 0.89592(17) 0.0357(4) Uani 1 1 d . C12 C 0.5911(3) 0.6135(2) 0.7803(2) 0.0446(4) Uani 1 1 d . C13 C 0.6149(3) 0.6875(2) 0.6810(2) 0.0465(4) Uani 1 1 d . H13 H 0.4944 0.6645 0.6086 0.056 Uiso 1 1 calc R C14 C 1.2272(4) 0.7947(4) 0.4326(3) 0.0695(7) Uani 1 1 d . H14 H 1.2250 0.7171 0.3386 0.083 Uiso 1 1 calc R H4 H 1.303(4) 0.957(3) 0.857(2) 0.071(8) Uiso 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 Cl1 0.0488(3) 0.0566(3) 0.0981(5) 0.0260(3) 0.0136(3) 0.0019(2) O2 0.0819(10) 0.0885(11) 0.0456(9) 0.0445(9) 0.0041(7) 0.0184(8) O3 0.0513(8) 0.0731(10) 0.0446(8) 0.0247(8) -0.0098(6) 0.0005(7) N4 0.0454(8) 0.0514(10) 0.0334(9) 0.0201(8) -0.0016(7) 0.0029(7) N5 0.0524(9) 0.0502(9) 0.0290(8) 0.0152(7) 0.0042(7) 0.0174(7) C6 0.0498(10) 0.0415(10) 0.0399(10) 0.0172(9) 0.0129(8) 0.0163(8) C7 0.0411(9) 0.0362(9) 0.0266(9) 0.0094(7) 0.0038(7) 0.0122(7) C8 0.0501(10) 0.0674(13) 0.0439(12) 0.0329(11) 0.0063(9) 0.0158(9) C9 0.0472(10) 0.0506(11) 0.0352(10) 0.0199(9) 0.0009(8) 0.0142(8) C10 0.0569(11) 0.0493(11) 0.0495(12) 0.0277(10) 0.0066(9) 0.0057(9) C11 0.0413(8) 0.0398(9) 0.0254(8) 0.0104(7) 0.0037(7) 0.0147(7) C12 0.0396(9) 0.0393(10) 0.0508(11) 0.0125(9) 0.0086(8) 0.0115(7) C13 0.0429(9) 0.0482(11) 0.0411(11) 0.0110(9) -0.0042(8) 0.0140(8) C14 0.0720(14) 0.1025(19) 0.0433(13) 0.0323(14) 0.0112(11) 0.0358(14) 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' Cl Cl 0.1484 0.1585 '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 N4 C10 124.60(15) C7 N4 H4 121.1(17) C10 N4 H4 114.3(17) O2 N5 O3 121.84(14) O2 N5 C11 118.93(15) O3 N5 C11 119.23(14) C11 C6 H6 120.2 C12 C6 H6 120.2 C12 C6 C11 119.54(16) N4 C7 C9 120.65(15) N4 C7 C11 124.46(14) C11 C7 C9 114.89(15) C14 C8 C10 178.9(2) C7 C9 H9 118.9 C13 C9 C7 122.28(16) C13 C9 H9 118.9 N4 C10 C8 113.91(16) N4 C10 H10A 108.8 N4 C10 H10B 108.8 C8 C10 H10A 108.8 C8 C10 H10B 108.8 H10A C10 H10B 107.7 C6 C11 N5 115.91(15) C6 C11 C7 122.56(15) C7 C11 N5 121.54(15) C6 C12 Cl1 120.48(14) C6 C12 C13 120.09(16) C13 C12 Cl1 119.43(14) C9 C13 C12 120.63(16) C9 C13 H13 119.7 C12 C13 H13 119.7 C8 C14 H14 180.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C12 1.7361(18) O2 N5 1.2273(18) O3 N5 1.230(2) N4 C7 1.342(2) N4 C10 1.452(2) N4 H4 0.79(2) N5 C11 1.446(2) C6 H6 0.9300 C6 C11 1.391(2) C6 C12 1.359(2) C7 C9 1.418(2) C7 C11 1.413(2) C8 C10 1.469(3) C8 C14 1.160(3) C9 H9 0.9300 C9 C13 1.357(2) C10 H10A 0.9700 C10 H10B 0.9700 C12 C13 1.387(3) C13 H13 0.9300 C14 H14 0.9300 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 Cl1 C12 C13 C9 -178.43(13) O2 N5 C11 C6 -1.6(2) O2 N5 C11 C7 178.90(15) O3 N5 C11 C6 178.57(15) O3 N5 C11 C7 -0.9(2) N4 C7 C9 C13 179.31(16) N4 C7 C11 N5 0.3(3) N4 C7 C11 C6 -179.17(16) C6 C12 C13 C9 0.8(3) C7 N4 C10 C8 -67.8(2) C7 C9 C13 C12 0.4(3) C9 C7 C11 N5 -178.80(14) C9 C7 C11 C6 1.7(2) C10 N4 C7 C9 -0.2(3) C10 N4 C7 C11 -179.22(16) C11 C6 C12 Cl1 178.59(12) C11 C6 C12 C13 -0.6(3) C11 C7 C9 C13 -1.6(2) C12 C6 C11 N5 179.79(14) C12 C6 C11 C7 -0.7(3) C14 C8 C10 N4 143(12)