#------------------------------------------------------------------------------ #$Date: 2019-11-22 19:33:15 +0200 (Fri, 22 Nov 2019) $ #$Revision: 231343 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/64/4516494.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_4516494 loop_ _publ_author_name 'Rybarczyk-Pirek, Agnieszka J.' '\/Lukomska-Rogala, Marlena' 'Wojtulewski, S\/lawomir' 'Palusiak, Marcin' _publ_section_title ; N-Oxide as a Proton Accepting Group in Multicomponent Crystals: X-ray and Theoretical Studies on New p-Nitropyridine-N-oxide Co-Crystals ; _journal_issue 12 _journal_name_full 'Crystal Growth & Design' _journal_page_first 5802 _journal_paper_doi 10.1021/acs.cgd.5b01177 _journal_volume 15 _journal_year 2015 _chemical_formula_sum 'C11 H12 N4 O5 S' _chemical_formula_weight 312.31 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _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 74.079(3) _cell_angle_beta 86.251(3) _cell_angle_gamma 70.884(3) _cell_formula_units_Z 2 _cell_length_a 8.0161(3) _cell_length_b 9.1719(3) _cell_length_c 9.6595(3) _cell_measurement_temperature 100(2) _cell_volume 645.06(4) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS (Sheldrich, 1986)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.4052 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'SuperNova, Dual, Mo at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 6299 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 2.81 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.60993 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 324 _exptl_crystal_size_max 0.539 _exptl_crystal_size_mid 0.224 _exptl_crystal_size_min 0.090 _refine_diff_density_max 0.450 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 206 _refine_ls_number_reflns 2398 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.149 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0282 _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^)+(0.0338P)^2^+0.4360P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.0815 _reflns_number_gt 2269 _reflns_number_total 2398 _reflns_threshold_expression >2sigma(I) _cod_data_source_file cg5b01177_si_002.cif _cod_data_source_block compound4 _cod_database_code 4516494 _shelx_res_file ; shelxl.res created by SHELXL-97 TITL exp_1803 in P-1 CELL 0.71073 8.0161 9.1719 9.6595 74.079 86.251 70.884 ZERR 2.00 0.0003 0.0003 0.0003 0.003 0.003 0.003 LATT 1 SFAC C H N O S UNIT 22 24 8 10 2 MERG 2 OMIT 0.00 51.00 FMAP 2 PLAN 6 ACTA BOND TEMP -173 L.S. 10 WGHT 0.033800 0.436000 FVAR 7.44036 H21 2 0.810403 0.540880 0.459869 11.00000 0.02555 H20 2 0.831197 0.400392 0.579410 11.00000 0.02620 H10 2 0.102057 0.312893 0.348127 11.00000 0.02731 H11 2 0.098154 0.452121 0.232622 11.00000 0.02428 MOLE 1 S11 5 0.312094 0.260709 0.205634 11.00000 0.01801 0.01577 = 0.01448 -0.00515 0.00159 -0.00806 C11 1 0.469816 0.309064 0.285864 11.00000 0.01367 0.01463 = 0.01595 -0.00576 0.00173 -0.00485 C16 1 0.519067 0.442972 0.215753 11.00000 0.01643 0.01399 = 0.01283 -0.00223 0.00085 -0.00355 AFIX 43 H16 2 0.472787 0.504058 0.121907 11.00000 -1.20000 AFIX 0 N1 3 0.842832 0.222881 0.935551 11.00000 0.01399 0.01274 = 0.01587 -0.00283 0.00132 -0.00202 C14 1 0.702613 0.398116 0.421955 11.00000 0.01360 0.01439 = 0.01567 -0.00524 0.00139 -0.00276 C15 1 0.634891 0.486706 0.282607 11.00000 0.01751 0.01263 = 0.01692 -0.00262 0.00260 -0.00523 AFIX 43 H15 2 0.669023 0.577243 0.234113 11.00000 -1.20000 AFIX 0 C12 1 0.538989 0.218384 0.422904 11.00000 0.01761 0.01252 = 0.01662 -0.00347 0.00369 -0.00530 AFIX 43 H12 2 0.506123 0.126817 0.470288 11.00000 -1.20000 AFIX 0 N20 3 0.821311 0.439617 0.489135 11.00000 0.02450 0.01713 = 0.01507 -0.00188 -0.00350 -0.00887 N10 3 0.117410 0.351780 0.257517 11.00000 0.01805 0.01974 = 0.01837 -0.00465 0.00106 -0.00875 C13 1 0.655453 0.261687 0.489904 11.00000 0.01916 0.01454 = 0.01285 -0.00150 -0.00006 -0.00311 AFIX 43 H13 2 0.703893 0.198552 0.582663 11.00000 -1.20000 AFIX 0 C4 1 0.811826 0.012987 1.189749 11.00000 0.01647 0.01314 = 0.01882 -0.00338 0.00549 -0.00240 O1 4 0.871900 0.313064 0.813066 11.00000 0.02559 0.01703 = 0.01347 0.00070 0.00063 -0.00700 C3 1 0.887254 0.128660 1.189695 11.00000 0.01917 0.01673 = 0.01549 -0.00602 0.00197 -0.00408 AFIX 43 H3 2 0.929433 0.135023 1.276786 11.00000 -1.20000 AFIX 0 O12 4 0.340407 0.091760 0.260778 11.00000 0.02848 0.01732 = 0.02552 -0.00714 -0.00046 -0.01009 O11 4 0.311514 0.327996 0.052346 11.00000 0.02835 0.03096 = 0.01432 -0.00670 0.00200 -0.01596 C2 1 0.899692 0.234144 1.060605 11.00000 0.01871 0.01484 = 0.01878 -0.00592 0.00090 -0.00617 AFIX 43 H2 2 0.948642 0.316020 1.058651 11.00000 -1.20000 AFIX 0 C6 1 0.760113 0.113635 0.937545 11.00000 0.01865 0.01852 = 0.02038 -0.00771 -0.00056 -0.00629 AFIX 43 H6 2 0.713375 0.111883 0.850359 11.00000 -1.20000 AFIX 0 C5 1 0.743856 0.006558 1.063994 11.00000 0.01711 0.01584 = 0.02634 -0.00758 0.00357 -0.00689 AFIX 43 H5 2 0.687413 -0.070175 1.065454 11.00000 -1.20000 AFIX 0 N4 3 0.807503 -0.107094 1.324169 11.00000 0.02319 0.01381 = 0.02288 -0.00332 0.00894 -0.00288 O41 4 0.876564 -0.103740 1.432638 11.00000 0.03942 0.02094 = 0.01816 -0.00226 0.00382 -0.00471 O42 4 0.735643 -0.205888 1.321294 11.00000 0.03569 0.02085 = 0.03630 -0.00293 0.01167 -0.01550 HKLF 4 REM exp_1803 in P-1 REM R1 = 0.0282 for 2269 Fo > 4sig(Fo) and 0.0297 for all 2398 data REM 206 parameters refined using 0 restraints END WGHT 0.0344 0.4282 REM Highest difference peak 0.450, deepest hole -0.421, 1-sigma level 0.048 Q1 1 0.3931 0.2865 0.2609 11.00000 0.05 0.45 Q2 1 0.2121 0.3143 0.2430 11.00000 0.05 0.27 Q3 1 0.6664 0.3427 0.4608 11.00000 0.05 0.25 Q4 1 0.6440 0.4599 0.3611 11.00000 0.05 0.24 Q5 1 0.8604 0.0630 1.1859 11.00000 0.05 0.23 Q6 1 0.4708 0.3826 0.2635 11.00000 0.05 0.23 ; loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-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 H21 H 0.810(3) 0.541(3) 0.460(2) 0.026(5) Uiso 1 1 d . H20 H 0.831(3) 0.400(3) 0.579(3) 0.026(5) Uiso 1 1 d . H10 H 0.102(3) 0.313(3) 0.348(3) 0.027(5) Uiso 1 1 d . H11 H 0.098(3) 0.452(3) 0.233(2) 0.024(5) Uiso 1 1 d . S11 S 0.31209(5) 0.26071(4) 0.20563(4) 0.01525(12) Uani 1 1 d . C11 C 0.46982(19) 0.30906(18) 0.28586(17) 0.0144(3) Uani 1 1 d . C16 C 0.5191(2) 0.44297(18) 0.21575(17) 0.0151(3) Uani 1 1 d . H16 H 0.4728 0.5041 0.1219 0.018 Uiso 1 1 calc R N1 N 0.84283(17) 0.22288(15) 0.93555(14) 0.0150(3) Uani 1 1 d . C14 C 0.7026(2) 0.39812(18) 0.42196(17) 0.0148(3) Uani 1 1 d . C15 C 0.6349(2) 0.48671(18) 0.28261(17) 0.0160(3) Uani 1 1 d . H15 H 0.6690 0.5772 0.2341 0.019 Uiso 1 1 calc R C12 C 0.5390(2) 0.21838(18) 0.42290(17) 0.0157(3) Uani 1 1 d . H12 H 0.5061 0.1268 0.4703 0.019 Uiso 1 1 calc R N20 N 0.82131(19) 0.43962(18) 0.48914(16) 0.0187(3) Uani 1 1 d . N10 N 0.11741(18) 0.35178(18) 0.25752(16) 0.0182(3) Uani 1 1 d . C13 C 0.6555(2) 0.26169(18) 0.48990(17) 0.0165(3) Uani 1 1 d . H13 H 0.7039 0.1986 0.5827 0.020 Uiso 1 1 calc R C4 C 0.8118(2) 0.01299(18) 1.18975(17) 0.0172(3) Uani 1 1 d . O1 O 0.87190(15) 0.31306(13) 0.81307(12) 0.0197(3) Uani 1 1 d . C3 C 0.8873(2) 0.12866(19) 1.18969(17) 0.0173(3) Uani 1 1 d . H3 H 0.9294 0.1350 1.2768 0.021 Uiso 1 1 calc R O12 O 0.34041(16) 0.09176(14) 0.26078(13) 0.0227(3) Uani 1 1 d . O11 O 0.31151(16) 0.32800(15) 0.05235(12) 0.0229(3) Uani 1 1 d . C2 C 0.8997(2) 0.23414(19) 1.06061(17) 0.0170(3) Uani 1 1 d . H2 H 0.9486 0.3160 1.0587 0.020 Uiso 1 1 calc R C6 C 0.7601(2) 0.11364(19) 0.93754(18) 0.0185(3) Uani 1 1 d . H6 H 0.7134 0.1119 0.8504 0.022 Uiso 1 1 calc R C5 C 0.7439(2) 0.00656(19) 1.06399(18) 0.0191(3) Uani 1 1 d . H5 H 0.6874 -0.0702 1.0655 0.023 Uiso 1 1 calc R N4 N 0.80750(19) -0.10709(16) 1.32417(16) 0.0215(3) Uani 1 1 d . O41 O 0.87656(18) -0.10374(15) 1.43264(13) 0.0282(3) Uani 1 1 d . O42 O 0.73564(18) -0.20589(15) 1.32129(15) 0.0308(3) 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 S11 0.0180(2) 0.0158(2) 0.0145(2) -0.00515(15) 0.00159(14) -0.00806(15) C11 0.0137(7) 0.0146(7) 0.0159(8) -0.0058(6) 0.0017(6) -0.0049(6) C16 0.0164(7) 0.0140(7) 0.0128(8) -0.0022(6) 0.0008(6) -0.0035(6) N1 0.0140(6) 0.0127(6) 0.0159(7) -0.0028(5) 0.0013(5) -0.0020(5) C14 0.0136(7) 0.0144(7) 0.0157(8) -0.0052(6) 0.0014(6) -0.0028(6) C15 0.0175(7) 0.0126(7) 0.0169(8) -0.0026(6) 0.0026(6) -0.0052(6) C12 0.0176(7) 0.0125(7) 0.0166(8) -0.0035(6) 0.0037(6) -0.0053(6) N20 0.0245(7) 0.0171(7) 0.0151(8) -0.0019(6) -0.0035(6) -0.0089(6) N10 0.0181(7) 0.0197(8) 0.0184(8) -0.0046(6) 0.0011(5) -0.0088(6) C13 0.0192(8) 0.0145(7) 0.0128(8) -0.0015(6) -0.0001(6) -0.0031(6) C4 0.0165(7) 0.0131(7) 0.0188(8) -0.0034(6) 0.0055(6) -0.0024(6) O1 0.0256(6) 0.0170(6) 0.0135(6) 0.0007(4) 0.0006(4) -0.0070(5) C3 0.0192(8) 0.0167(8) 0.0155(8) -0.0060(6) 0.0020(6) -0.0041(6) O12 0.0285(6) 0.0173(6) 0.0255(7) -0.0071(5) -0.0005(5) -0.0101(5) O11 0.0283(6) 0.0310(7) 0.0143(6) -0.0067(5) 0.0020(5) -0.0160(5) C2 0.0187(8) 0.0148(7) 0.0188(8) -0.0059(6) 0.0009(6) -0.0062(6) C6 0.0187(8) 0.0185(8) 0.0204(8) -0.0077(6) -0.0006(6) -0.0063(6) C5 0.0171(8) 0.0158(8) 0.0263(9) -0.0076(7) 0.0036(6) -0.0069(6) N4 0.0232(7) 0.0138(7) 0.0229(8) -0.0033(6) 0.0089(6) -0.0029(6) O41 0.0394(7) 0.0209(6) 0.0182(6) -0.0023(5) 0.0038(5) -0.0047(5) O42 0.0357(7) 0.0209(6) 0.0363(8) -0.0029(5) 0.0117(6) -0.0155(6) 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' S S 0.1246 0.1234 '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 O12 S11 O11 118.90(7) O12 S11 N10 106.48(8) O11 S11 N10 105.82(8) O12 S11 C11 108.60(7) O11 S11 C11 108.38(7) N10 S11 C11 108.21(7) C12 C11 C16 120.03(14) C12 C11 S11 119.82(12) C16 C11 S11 120.07(12) C15 C16 C11 120.08(14) O1 N1 C2 119.93(13) O1 N1 C6 119.72(13) C2 N1 C6 120.31(14) N20 C14 C13 120.13(14) N20 C14 C15 120.80(14) C13 C14 C15 118.99(14) C16 C15 C14 120.38(14) C13 C12 C11 119.99(14) C12 C13 C14 120.49(14) C3 C4 C5 121.23(15) C3 C4 N4 119.38(15) C5 C4 N4 119.37(14) C2 C3 C4 118.34(15) N1 C2 C3 120.83(14) N1 C6 C5 120.70(15) C6 C5 C4 118.36(15) O41 N4 O42 124.11(15) O41 N4 C4 118.13(14) O42 N4 C4 117.76(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S11 O12 1.4384(12) S11 O11 1.4391(12) S11 N10 1.6303(14) S11 C11 1.7549(15) C11 C12 1.393(2) C11 C16 1.396(2) C16 C15 1.380(2) N1 O1 1.3006(17) N1 C2 1.360(2) N1 C6 1.366(2) C14 N20 1.387(2) C14 C13 1.402(2) C14 C15 1.405(2) C12 C13 1.382(2) C4 C3 1.382(2) C4 C5 1.387(2) C4 N4 1.461(2) C3 C2 1.373(2) C6 C5 1.371(2) N4 O41 1.229(2) N4 O42 1.2294(19)