#------------------------------------------------------------------------------ #$Date: 2018-01-11 07:09:09 +0200 (Thu, 11 Jan 2018) $ #$Revision: 205067 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229949.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_7229949 loop_ _publ_author_name 'B\"ohnke, Hendrik' 'Bahrenburg, Julia' 'Ma, Xiaonan' 'R\"ottger, Katharina' 'N\"ather, Christian' 'Rode, Micha\/l F.' 'Sobolewski, Andrzej L.' 'Temps, Friedrich' _publ_section_title ; Ultrafast dynamics of the ESIPT photoswitch N-(3-pyridinyl)-2-pyridinecarboxamide ; _journal_name_full 'Physical Chemistry Chemical Physics' _journal_paper_doi 10.1039/C7CP06145E _journal_year 2018 _chemical_formula_sum 'C11 H9 N3 O' _chemical_formula_weight 199.21 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014 _audit_update_record ; 2017-06-16 deposited with the CCDC. 2018-01-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.120(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.7147(4) _cell_length_b 8.3019(6) _cell_length_c 20.1261(14) _cell_measurement_reflns_used 11185 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.242 _cell_measurement_theta_min 2.029 _cell_volume 952.37(12) _computing_cell_refinement 'X-Area (STOE, 2010)' _computing_data_collection 'X-Area (STOE, 2010)' _computing_data_reduction 'X-Area (STOE, 2010)' _computing_molecular_graphics 'Diamond (Brandenburg)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'STOE IPDS-2' _diffrn_measurement_method 'Omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_unetI/netI 0.0321 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 10738 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.002 _diffrn_reflns_theta_min 2.029 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.389 _exptl_crystal_description block _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.130 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.028 _refine_ls_extinction_coef 0.031(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 1875 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0456 _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^)+(0.0446P)^2^+0.1674P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0985 _refine_ls_wR_factor_ref 0.1058 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1508 _reflns_number_total 1875 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7cp06145e2.cif _cod_data_source_block temps3new _cod_database_code 7229949 _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. ; _shelxl_version_number 2014-3 _shelx_res_file ; TITL C11H9N3O at rt in P2(1)/n (Temps3a) CELL 0.71073 5.7147 8.3019 20.1261 90.000 94.120 90.0000 ZERR 4.00 0.0004 0.0006 0.0014 0.000 0.005 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 44 36 12 4 L.S. 10 ACTA HTAB HTAB N1 N3 HTAB C3 O1 EQIV $1 x-1, y, z HTAB C6 O1_$1 EQIV $2 x-1/2, -y+1/2, z-1/2 HTAB C9 N2_$2 WGHT 0.044600 0.167400 EXTI 0.031126 FVAR 1.41618 C1 1 0.624805 0.312725 0.558566 11.00000 0.04208 0.04423 = 0.04425 0.00104 -0.00009 -0.00264 O1 4 0.824020 0.317069 0.585629 11.00000 0.04313 0.08348 = 0.06195 -0.02274 -0.00559 -0.00138 N1 3 0.433438 0.377240 0.584561 11.00000 0.03996 0.05038 = 0.04580 -0.00554 -0.00225 0.00016 AFIX 43 H1 2 0.301799 0.362848 0.561856 11.00000 -1.20000 AFIX 0 C2 1 0.423998 0.464833 0.644134 11.00000 0.04201 0.03956 = 0.03969 0.00140 0.00303 -0.00451 C3 1 0.606144 0.470930 0.693291 11.00000 0.05032 0.07515 = 0.04202 -0.00322 -0.00267 0.01274 AFIX 43 H3 2 0.741321 0.412051 0.687120 11.00000 -1.20000 AFIX 0 N2 3 0.597670 0.556891 0.749023 11.00000 0.05997 0.08232 = 0.04162 -0.00661 -0.00392 0.00837 C4 1 0.402537 0.638590 0.757751 11.00000 0.06074 0.05639 = 0.04064 -0.00205 0.00739 -0.00276 AFIX 43 H4 2 0.395632 0.700231 0.796144 11.00000 -1.20000 AFIX 0 C5 1 0.210565 0.636222 0.712699 11.00000 0.04921 0.05803 = 0.05653 -0.00798 0.00785 0.00294 AFIX 43 H5 2 0.075332 0.692764 0.721095 11.00000 -1.20000 AFIX 0 C6 1 0.221388 0.548734 0.654828 11.00000 0.04033 0.05290 = 0.05160 -0.00200 -0.00260 -0.00146 AFIX 43 H6 2 0.093975 0.546203 0.623383 11.00000 -1.20000 AFIX 0 C7 1 0.574857 0.229138 0.493152 11.00000 0.04029 0.04221 = 0.04002 0.00396 0.00102 -0.00400 N3 3 0.360110 0.245638 0.462698 11.00000 0.04156 0.05657 = 0.04355 0.00235 -0.00089 -0.00089 C8 1 0.319426 0.168189 0.405353 11.00000 0.04612 0.06792 = 0.04258 0.00429 -0.00568 -0.00683 AFIX 43 H8 2 0.172947 0.180666 0.382673 11.00000 -1.20000 AFIX 0 C9 1 0.480398 0.070463 0.377278 11.00000 0.06030 0.06154 = 0.03749 -0.00398 0.00161 -0.01475 AFIX 43 H9 2 0.441959 0.016489 0.337493 11.00000 -1.20000 AFIX 0 C10 1 0.698853 0.054923 0.409581 11.00000 0.05317 0.05907 = 0.05109 -0.00888 0.00683 -0.00032 AFIX 43 H10 2 0.811705 -0.010368 0.392176 11.00000 -1.20000 AFIX 0 C11 1 0.748169 0.137507 0.468131 11.00000 0.03960 0.05342 = 0.04849 -0.00236 -0.00112 -0.00117 AFIX 43 H11 2 0.896258 0.131408 0.490385 11.00000 -1.20000 AFIX 0 HKLF 4 REM C11H9N3O at rt in P2(1)/n (Temps3a) REM R1 = 0.0456 for 1508 Fo > 4sig(Fo) and 0.0631 for all 1875 data REM 137 parameters refined using 0 restraints END WGHT 0.0444 0.1681 REM Instructions for potential hydrogen bonds HTAB N1 N3 HTAB C3 O1 HTAB C6 O1_$1 HTAB C9 N2_$2 REM Highest difference peak 0.130, deepest hole -0.135, 1-sigma level 0.028 Q1 1 0.5878 0.3090 0.5170 11.00000 0.05 0.13 Q2 1 0.3240 0.3794 0.4809 11.00000 0.05 0.12 Q3 1 0.7778 0.4237 0.5739 11.00000 0.05 0.12 Q4 1 0.3417 0.4177 0.5373 11.00000 0.05 0.12 Q5 1 0.5689 0.2290 0.5360 11.00000 0.05 0.11 Q6 1 0.4605 0.6485 0.8161 11.00000 0.05 0.11 Q7 1 0.5918 0.4633 0.7414 11.00000 0.05 0.11 Q8 1 0.5426 0.5374 0.6605 11.00000 0.05 0.10 Q9 1 0.0776 0.2367 0.3886 11.00000 0.05 0.10 Q10 1 0.7841 0.3206 0.6468 11.00000 0.05 0.10 Q11 1 0.8029 0.1837 0.5764 11.00000 0.05 0.10 Q12 1 0.6344 0.5382 0.7980 11.00000 0.05 0.10 Q13 1 0.4480 0.4824 0.5958 11.00000 0.05 0.10 Q14 1 0.5446 0.4279 0.5538 11.00000 0.05 0.09 Q15 1 0.4820 0.5510 0.7614 11.00000 0.05 0.09 Q16 1 0.2879 0.5678 0.7345 11.00000 0.05 0.09 Q17 1 0.4383 0.0593 0.3231 11.00000 0.05 0.09 Q18 1 0.6020 0.1487 0.3897 11.00000 0.05 0.09 Q19 1 0.7681 0.4606 0.7845 11.00000 0.05 0.09 Q20 1 0.6677 0.2320 0.4724 11.00000 0.05 0.09 ; _shelx_res_checksum 17347 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 C1 C 0.6248(3) 0.3127(2) 0.55857(8) 0.0437(4) Uani 1 1 d . . O1 O 0.8240(2) 0.31707(17) 0.58563(6) 0.0633(4) Uani 1 1 d . . N1 N 0.4334(2) 0.37724(16) 0.58456(7) 0.0456(4) Uani 1 1 d . . H1 H 0.3018 0.3628 0.5619 0.055 Uiso 1 1 calc R U C2 C 0.4240(3) 0.46483(18) 0.64413(8) 0.0404(4) Uani 1 1 d . . C3 C 0.6061(3) 0.4709(2) 0.69329(8) 0.0561(5) Uani 1 1 d . . H3 H 0.7413 0.4121 0.6871 0.067 Uiso 1 1 calc R U N2 N 0.5977(3) 0.5569(2) 0.74902(7) 0.0617(5) Uani 1 1 d . . C4 C 0.4025(3) 0.6386(2) 0.75775(8) 0.0524(4) Uani 1 1 d . . H4 H 0.3956 0.7002 0.7961 0.063 Uiso 1 1 calc R U C5 C 0.2106(3) 0.6362(2) 0.71270(9) 0.0544(5) Uani 1 1 d . . H5 H 0.0753 0.6928 0.7211 0.065 Uiso 1 1 calc R U C6 C 0.2214(3) 0.5487(2) 0.65483(9) 0.0486(4) Uani 1 1 d . . H6 H 0.0940 0.5462 0.6234 0.058 Uiso 1 1 calc R U C7 C 0.5749(3) 0.22914(19) 0.49315(8) 0.0409(4) Uani 1 1 d . . N3 N 0.3601(2) 0.24564(18) 0.46270(7) 0.0474(4) Uani 1 1 d . . C8 C 0.3194(3) 0.1682(2) 0.40535(8) 0.0526(5) Uani 1 1 d . . H8 H 0.1729 0.1807 0.3827 0.063 Uiso 1 1 calc R U C9 C 0.4804(3) 0.0705(2) 0.37728(8) 0.0532(5) Uani 1 1 d . . H9 H 0.4420 0.0165 0.3375 0.064 Uiso 1 1 calc R U C10 C 0.6989(3) 0.0549(2) 0.40958(9) 0.0543(5) Uani 1 1 d . . H10 H 0.8117 -0.0104 0.3922 0.065 Uiso 1 1 calc R U C11 C 0.7482(3) 0.1375(2) 0.46813(8) 0.0474(4) Uani 1 1 d . . H11 H 0.8963 0.1314 0.4904 0.057 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 C1 0.0421(9) 0.0442(9) 0.0443(9) 0.0010(7) -0.0001(7) -0.0026(7) O1 0.0431(7) 0.0835(10) 0.0620(8) -0.0227(7) -0.0056(6) -0.0014(6) N1 0.0400(7) 0.0504(8) 0.0458(8) -0.0055(6) -0.0023(6) 0.0002(6) C2 0.0420(8) 0.0396(8) 0.0397(8) 0.0014(6) 0.0030(6) -0.0045(7) C3 0.0503(10) 0.0752(13) 0.0420(9) -0.0032(8) -0.0027(7) 0.0127(9) N2 0.0600(10) 0.0823(12) 0.0416(8) -0.0066(8) -0.0039(7) 0.0084(8) C4 0.0607(11) 0.0564(11) 0.0406(9) -0.0021(8) 0.0074(8) -0.0028(9) C5 0.0492(10) 0.0580(11) 0.0565(10) -0.0080(9) 0.0079(8) 0.0029(8) C6 0.0403(9) 0.0529(10) 0.0516(9) -0.0020(8) -0.0026(7) -0.0015(7) C7 0.0403(8) 0.0422(8) 0.0400(8) 0.0040(7) 0.0010(6) -0.0040(7) N3 0.0416(7) 0.0566(8) 0.0436(7) 0.0023(6) -0.0009(6) -0.0009(6) C8 0.0461(9) 0.0679(12) 0.0426(9) 0.0043(8) -0.0057(7) -0.0068(8) C9 0.0603(11) 0.0615(11) 0.0375(8) -0.0040(8) 0.0016(8) -0.0147(9) C10 0.0532(10) 0.0591(11) 0.0511(10) -0.0089(8) 0.0068(8) -0.0003(8) C11 0.0396(8) 0.0534(10) 0.0485(9) -0.0024(8) -0.0011(7) -0.0012(7) 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 O1 C1 N1 124.44(15) O1 C1 C7 121.08(15) N1 C1 C7 114.47(14) C1 N1 C2 127.91(14) C6 C2 C3 117.76(15) C6 C2 N1 118.52(14) C3 C2 N1 123.72(15) N2 C3 C2 123.36(17) C4 N2 C3 117.80(16) N2 C4 C5 122.99(16) C4 C5 C6 118.93(16) C5 C6 C2 119.12(16) N3 C7 C11 123.40(15) N3 C7 C1 117.75(14) C11 C7 C1 118.83(14) C8 N3 C7 116.50(15) N3 C8 C9 124.16(16) C10 C9 C8 118.21(16) C9 C10 C11 118.87(17) C7 C11 C10 118.80(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.227(2) C1 N1 1.356(2) C1 C7 1.497(2) N1 C2 1.407(2) C2 C6 1.381(2) C2 C3 1.385(2) C3 N2 1.333(2) N2 C4 1.328(2) C4 C5 1.372(3) C5 C6 1.378(2) C7 N3 1.339(2) C7 C11 1.373(2) N3 C8 1.327(2) C8 C9 1.378(3) C9 C10 1.372(3) C10 C11 1.375(2) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.86 2.27 2.6902(19) 110.4 . C3 H3 O1 0.93 2.27 2.875(2) 122.1 . C6 H6 O1 0.93 2.53 3.216(2) 130.7 1_455 C9 H9 N2 0.93 2.63 3.428(2) 144.5 4_565