data_shelx _audit_creation_method SHELXL-2013 _chemical_name_systematic 'a-(5-chloro-2-pyridylamino)-o-cresol' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 Cl N2 O' _chemical_formula_weight 234.68 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3999(13) _cell_length_b 7.8507(16) _cell_length_c 12.042(2) _cell_angle_alpha 100.61(3) _cell_angle_beta 102.31(3) _cell_angle_gamma 101.19(3) _cell_volume 563.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 29.08 _exptl_crystal_description 'Prism' _exptl_crystal_colour 'Colorless' _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_F_000 244 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_absorpt_coefficient_mu 0.317 _shelx_estimated_absorpt_T_min ? _shelx_estimated_absorpt_T_max ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'Sealed tube' _diffrn_measurement_device_type 'Rigaku Saturn 720+ CCD' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_reflns_number 10218 _diffrn_reflns_av_unetI/netI 0.1168 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.359 _diffrn_reflns_theta_max 27.480 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_point_group_measured_fraction_full 0.997 _reflns_number_total 2569 _reflns_number_gt 1385 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Data were apparently pre-merged, so _diffrn_reflns_number etc. will have to be added later. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0228P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2569 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1282 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 0.895 _refine_ls_restrained_S_all 0.895 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Cl1 Cl 0.06736(12) 0.95048(10) 0.67644(6) 0.0652(3) Uani 1 1 d . . . . . O O 0.0815(2) 1.3861(2) 1.16030(14) 0.0538(5) Uani 1 1 d . . . . . H1 H 0.1467 1.3255 1.1238 0.081 Uiso 1 1 calc R U . . . N1 N 0.6018(3) 1.3396(3) 1.14113(17) 0.0475(5) Uani 1 1 d . . . . . H1A H 0.7324 1.4035 1.1503 0.057 Uiso 1 1 calc R U . . . C2 C 0.5755(4) 1.6054(3) 1.3993(2) 0.0450(6) Uani 1 1 d . . . . . H2 H 0.7190 1.5967 1.4279 0.054 Uiso 1 1 calc R U . . . N2 N 0.2620(3) 1.1960(3) 1.01338(16) 0.0418(5) Uani 1 1 d . . . . . C1 C 0.4424(4) 1.4809(3) 1.29974(19) 0.0358(6) Uani 1 1 d . . . . . C10 C 0.2324(4) 1.0743(3) 0.8121(2) 0.0424(6) Uani 1 1 d . . . . . C9 C 0.1423(4) 1.1048(3) 0.9051(2) 0.0459(6) Uani 1 1 d . . . . . H9 H -0.0085 1.0607 0.8930 0.055 Uiso 1 1 calc R U . . . C6 C 0.2286(4) 1.4997(3) 1.25776(19) 0.0376(6) Uani 1 1 d . . . . . C11 C 0.4554(4) 1.1452(3) 0.8277(2) 0.0452(6) Uani 1 1 d . . . . . H11 H 0.5192 1.1307 0.7652 0.054 Uiso 1 1 calc R U . . . C8 C 0.4795(4) 1.2567(3) 1.0304(2) 0.0372(6) Uani 1 1 d . . . . . C12 C 0.5794(4) 1.2370(3) 0.9370(2) 0.0431(6) Uani 1 1 d . . . . . H12 H 0.7293 1.2862 0.9497 0.052 Uiso 1 1 calc R U . . . C7 C 0.5235(4) 1.3260(3) 1.24534(19) 0.0450(6) Uani 1 1 d . . . . . H7A H 0.6426 1.3095 1.3041 0.054 Uiso 1 1 calc R U . . . H7B H 0.4046 1.2191 1.2254 0.054 Uiso 1 1 calc R U . . . C4 C 0.2911(5) 1.7557(3) 1.4155(2) 0.0517(7) Uani 1 1 d . . . . . H4 H 0.2400 1.8462 1.4545 0.062 Uiso 1 1 calc R U . . . C5 C 0.1545(4) 1.6366(3) 1.3161(2) 0.0471(6) Uani 1 1 d . . . . . H5 H 0.0120 1.6478 1.2878 0.057 Uiso 1 1 calc R U . . . C3 C 0.5029(4) 1.7414(3) 1.4573(2) 0.0502(7) Uani 1 1 d . . . . . H3 H 0.5960 1.8225 1.5239 0.060 Uiso 1 1 calc R U . . . 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 0.0655(5) 0.0740(5) 0.0452(4) -0.0026(3) 0.0003(3) 0.0231(4) O 0.0296(9) 0.0644(12) 0.0547(12) -0.0108(9) 0.0058(8) 0.0109(9) N1 0.0283(11) 0.0546(14) 0.0484(14) -0.0032(10) 0.0108(10) -0.0024(11) C2 0.0409(15) 0.0488(16) 0.0405(15) 0.0110(12) 0.0044(12) 0.0063(13) N2 0.0292(11) 0.0503(13) 0.0420(13) 0.0028(9) 0.0095(9) 0.0077(10) C1 0.0335(13) 0.0359(13) 0.0376(14) 0.0088(10) 0.0097(11) 0.0072(12) C10 0.0446(15) 0.0412(15) 0.0395(15) 0.0069(11) 0.0062(12) 0.0141(13) C9 0.0330(14) 0.0483(16) 0.0498(17) 0.0017(12) 0.0070(12) 0.0080(13) C6 0.0330(13) 0.0362(14) 0.0391(15) 0.0031(11) 0.0107(11) 0.0021(12) C11 0.0508(17) 0.0462(16) 0.0488(17) 0.0165(12) 0.0244(13) 0.0179(14) C8 0.0323(14) 0.0341(13) 0.0465(15) 0.0076(11) 0.0120(11) 0.0104(12) C12 0.0323(13) 0.0447(15) 0.0535(17) 0.0091(12) 0.0174(12) 0.0074(13) C7 0.0392(15) 0.0493(16) 0.0433(16) 0.0065(12) 0.0042(12) 0.0147(13) C4 0.0667(19) 0.0369(15) 0.0547(18) 0.0058(12) 0.0250(15) 0.0146(15) C5 0.0414(15) 0.0499(16) 0.0528(17) 0.0083(13) 0.0179(13) 0.0144(14) C3 0.0578(18) 0.0413(15) 0.0403(16) 0.0005(12) 0.0067(13) 0.0010(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl1 C10 1.735(2) . ? O C6 1.370(3) . ? O H1 0.8200 . ? N1 C8 1.361(3) . ? N1 C7 1.461(3) . ? N1 H1A 0.8600 . ? C2 C3 1.378(3) . ? C2 C1 1.388(3) . ? C2 H2 0.9300 . ? N2 C8 1.339(3) . ? N2 C9 1.348(3) . ? C1 C6 1.400(3) . ? C1 C7 1.508(3) . ? C10 C9 1.369(3) . ? C10 C11 1.386(3) . ? C9 H9 0.9300 . ? C6 C5 1.391(3) . ? C11 C12 1.365(3) . ? C11 H11 0.9300 . ? C8 C12 1.406(3) . ? C12 H12 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C4 C3 1.376(3) . ? C4 C5 1.377(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C3 H3 0.9300 . ? 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 C6 O H1 109.5 . . ? C8 N1 C7 123.6(2) . . ? C8 N1 H1A 118.2 . . ? C7 N1 H1A 118.2 . . ? C3 C2 C1 122.4(2) . . ? C3 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? C8 N2 C9 118.0(2) . . ? C2 C1 C6 117.3(2) . . ? C2 C1 C7 120.3(2) . . ? C6 C1 C7 122.2(2) . . ? C9 C10 C11 119.1(2) . . ? C9 C10 Cl1 120.0(2) . . ? C11 C10 Cl1 120.84(19) . . ? N2 C9 C10 123.1(2) . . ? N2 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? O C6 C5 116.6(2) . . ? O C6 C1 123.03(19) . . ? C5 C6 C1 120.4(2) . . ? C12 C11 C10 118.5(2) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? N2 C8 N1 117.9(2) . . ? N2 C8 C12 121.3(2) . . ? N1 C8 C12 120.7(2) . . ? C11 C12 C8 119.7(2) . . ? C11 C12 H12 120.1 . . ? C8 C12 H12 120.1 . . ? N1 C7 C1 116.98(19) . . ? N1 C7 H7A 108.1 . . ? C1 C7 H7A 108.1 . . ? N1 C7 H7B 108.1 . . ? C1 C7 H7B 108.1 . . ? H7A C7 H7B 107.3 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? _refine_diff_density_max 0.233 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.046 _shelxl_version_number 2013-4 # start validation Reply form _vrf_STRVA01 ; PROBLEM: _refine_ls_abs_structure_Flack 0.600 RESPONSE: The Flack paramter cannot be used reliably in this study since the heaviest element is oxygen ; _vrf_PLAT907 ; PROBLEM: Flack x > 0.5, Structure Needs to be Inverted? . 0.60 Check RESPONSE: The Flack paramter cannot be used reliably in this study since the heaviest element is oxygen ; # end validation Reply form _shelx_res_file ; TITL S559520 in P-1 CELL 0.71073 6.3999 7.8507 12.0418 100.612 102.314 101.186 ZERR 2.00 0.0013 0.0016 0.0024 0.030 0.030 0.030 LATT 1 SFAC C H N O CL UNIT 24 22 4 2 2 MERG 2 OMIT 0 2 0 OMIT -2 0 2 FMAP 2 PLAN 20 BOND $H ACTA L.S. 4 WGHT 0.022800 FVAR 0.32445 MOLE 1 CL1 5 0.067358 0.950477 0.676436 11.00000 0.06549 0.07405 = 0.04523 -0.00258 0.00030 0.02310 O 4 0.081517 1.386134 1.160298 11.00000 0.02963 0.06440 = 0.05470 -0.01083 0.00580 0.01088 AFIX 147 H1 2 0.146672 1.325454 1.123773 11.00000 -1.50000 AFIX 0 N1 3 0.601833 1.339612 1.141133 11.00000 0.02829 0.05460 = 0.04838 -0.00319 0.01083 -0.00244 AFIX 43 H1A 2 0.732353 1.403545 1.150260 11.00000 -1.20000 AFIX 0 C2 1 0.575546 1.605390 1.399290 11.00000 0.04090 0.04875 = 0.04054 0.01096 0.00437 0.00631 AFIX 43 H2 2 0.719047 1.596687 1.427910 11.00000 -1.20000 AFIX 0 N2 3 0.261961 1.195958 1.013377 11.00000 0.02920 0.05028 = 0.04197 0.00277 0.00950 0.00771 C1 1 0.442421 1.480927 1.299738 11.00000 0.03346 0.03595 = 0.03764 0.00882 0.00966 0.00720 C10 1 0.232449 1.074263 0.812105 11.00000 0.04464 0.04119 = 0.03951 0.00686 0.00618 0.01408 C9 1 0.142322 1.104837 0.905093 11.00000 0.03295 0.04828 = 0.04985 0.00170 0.00698 0.00803 AFIX 43 H9 2 -0.008522 1.060659 0.892969 11.00000 -1.20000 AFIX 0 C6 1 0.228589 1.499674 1.257756 11.00000 0.03296 0.03620 = 0.03914 0.00308 0.01067 0.00212 C11 1 0.455391 1.145206 0.827740 11.00000 0.05075 0.04624 = 0.04885 0.01647 0.02441 0.01789 AFIX 43 H11 2 0.519160 1.130654 0.765167 11.00000 -1.20000 AFIX 0 C8 1 0.479474 1.256658 1.030389 11.00000 0.03225 0.03408 = 0.04652 0.00765 0.01199 0.01039 C12 1 0.579403 1.236951 0.937038 11.00000 0.03232 0.04470 = 0.05354 0.00909 0.01743 0.00745 AFIX 43 H12 2 0.729288 1.286188 0.949689 11.00000 -1.20000 AFIX 0 C7 1 0.523514 1.325955 1.245341 11.00000 0.03921 0.04935 = 0.04329 0.00650 0.00418 0.01472 AFIX 23 H7A 2 0.642618 1.309470 1.304138 11.00000 -1.20000 H7B 2 0.404580 1.219088 1.225352 11.00000 -1.20000 AFIX 0 C4 1 0.291103 1.755734 1.415501 11.00000 0.06674 0.03687 = 0.05470 0.00580 0.02499 0.01455 AFIX 43 H4 2 0.240026 1.846200 1.454538 11.00000 -1.20000 AFIX 0 C5 1 0.154500 1.636621 1.316094 11.00000 0.04141 0.04985 = 0.05276 0.00829 0.01789 0.01442 AFIX 43 H5 2 0.011993 1.647759 1.287802 11.00000 -1.20000 AFIX 0 C3 1 0.502913 1.741350 1.457265 11.00000 0.05779 0.04135 = 0.04029 0.00048 0.00670 0.00095 AFIX 43 H3 2 0.596041 1.822473 1.523877 11.00000 -1.20000 AFIX 0 HKLF 4 REM S559520 in P-1 REM R1 = 0.0575 for 1385 Fo > 4sig(Fo) and 0.1282 for all 2569 data REM 146 parameters refined using 0 restraints END WGHT 0.0226 0.0000 REM Highest difference peak 0.233, deepest hole -0.219, 1-sigma level 0.046 Q1 1 0.7575 1.3227 1.1467 11.00000 0.05 0.23 Q2 1 0.5093 0.9882 0.6591 11.00000 0.05 0.16 Q3 1 0.3882 1.7005 1.4407 11.00000 0.05 0.15 Q4 1 0.8952 1.3547 1.1780 11.00000 0.05 0.15 Q5 1 0.3960 1.1778 1.0178 11.00000 0.05 0.15 Q6 1 0.6994 1.8777 1.3982 11.00000 0.05 0.14 Q7 1 0.4705 1.5131 1.3777 11.00000 0.05 0.14 Q8 1 0.1900 1.6117 1.2636 11.00000 0.05 0.14 Q9 1 0.3574 0.8775 0.8222 11.00000 0.05 0.13 Q10 1 0.5041 1.7639 1.3934 11.00000 0.05 0.13 Q11 1 0.3650 1.0436 0.6569 11.00000 0.05 0.13 Q12 1 0.1923 1.7609 1.2346 11.00000 0.05 0.13 Q13 1 0.1364 1.8663 1.4775 11.00000 0.05 0.13 Q14 1 0.8029 1.2199 1.2345 11.00000 0.05 0.12 Q15 1 -0.0050 0.7067 0.6808 11.00000 0.05 0.12 Q16 1 -0.0095 1.4366 1.3408 11.00000 0.05 0.12 Q17 1 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