#------------------------------------------------------------------------------ #$Date: 2016-05-11 06:34:41 +0300 (Wed, 11 May 2016) $ #$Revision: 182860 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/32/1543275.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_1543275 loop_ _publ_author_name 'Sivakumar, P.' 'Sudhahar, S.' 'Israel, S.' 'Chakkaravarthi, G.' _publ_section_title ; 2-Amino-6-methylpyridinium 2-hydroxybenzoate ; _journal_coeditor_code BT4008 _journal_issue 5 _journal_name_full IUCrData _journal_page_first x160747 _journal_paper_doi 10.1107/S2414314616007471 _journal_volume 1 _journal_year 2016 _chemical_formula_iupac 'C6 H9 N2 +, C7 H5 O3 -' _chemical_formula_moiety 'C6 H9 N2 +, C7 H5 O3 -' _chemical_formula_sum 'C13 H14 N2 O3' _chemical_formula_weight 246.26 _chemical_name_systematic ; 2-Amino-6-methylpyridinium 2-hydroxybenzoate ; _space_group_IT_number 88 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall '-I 4ad' _symmetry_space_group_name_H-M 'I 41/a :2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 16 _cell_length_a 14.1096(6) _cell_length_b 14.1096(6) _cell_length_c 24.6537(11) _cell_measurement_reflns_used 9075 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.3 _cell_measurement_theta_min 2.6 _cell_volume 4908.1(4) _computing_cell_refinement ; SAINT (Bruker, 2004) ; _computing_data_collection ; APEX2 (Bruker, 2004) ; _computing_data_reduction ; SAINT (Bruker, 2004) ; _computing_molecular_graphics ; PLATON (Spek, 2009) ; _computing_publication_material ; SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009) ; _computing_structure_refinement ; SHELXL97 (Sheldrick, 2008) ; _computing_structure_solution ; SHELXS97 (Sheldrick, 2008) ; _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 33461 _diffrn_reflns_theta_full 27.09 _diffrn_reflns_theta_max 27.09 _diffrn_reflns_theta_min 2.63 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_correction_T_min 0.9736 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 2004) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2080 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.169 _refine_diff_density_min -0.177 _refine_ls_extinction_coef 0.0018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method ; SHELXL97 (Sheldrick, 2008) ; _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 169 _refine_ls_number_reflns 2705 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.052 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0546 _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^)+(0.0790P)^2^+4.2162P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1401 _refine_ls_wR_factor_ref 0.1910 _reflns_number_gt 1564 _reflns_number_total 2705 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL J in I4(1)/a CELL 0.71073 14.1096 14.1096 24.6537 90.000 90.000 90.000 ZERR 16.00 0.0006 0.0006 0.0011 0.000 0.000 0.000 LATT 2 SYMM - X, 1/2 - Y, Z SYMM 3/4 - Y, 1/4 + X, 1/4 + Z SYMM 1/4 + Y, 1/4 - X, 1/4 + Z SFAC C H N O UNIT 208 224 32 48 MERG 2 OMIT 0 1 1 DFIX 0.820 0.010 O1 H1A FMAP 2 PLAN 25 HTAB O1 O2 HTAB N1 O2_$1 HTAB N2 O3_$1 HTAB N2 O3_$2 EQIV $1 -x,1-y,1-z EQIV $2 -1/4+y,3/4-x,-1/4+z SIZE 0.20 0.24 0.28 ACTA BOND $H CONF L.S. 4 WGHT 0.079000 4.216200 EXTI 0.001847 FVAR 0.06133 C1 1 0.346593 0.361439 0.532271 11.00000 0.07034 0.12062 = 0.04908 -0.00418 -0.00324 0.00825 AFIX 43 H1 2 0.328745 0.359693 0.568571 11.00000 -1.20000 AFIX 0 C2 1 0.440276 0.371835 0.519241 11.00000 0.06831 0.21018 = 0.07092 -0.01482 -0.01427 0.00332 AFIX 43 H2 2 0.485438 0.377867 0.546500 11.00000 -1.20000 AFIX 0 C3 1 0.467354 0.373326 0.465712 11.00000 0.06106 0.18733 = 0.07810 -0.02104 0.00488 -0.00122 AFIX 43 H3 2 0.531092 0.379789 0.456842 11.00000 -1.20000 AFIX 0 C4 1 0.401993 0.365464 0.425811 11.00000 0.06994 0.10506 = 0.05896 -0.00681 0.01150 0.00305 AFIX 43 H4 2 0.420985 0.366644 0.389695 11.00000 -1.20000 AFIX 0 C5 1 0.307323 0.355708 0.438507 11.00000 0.06488 0.06308 = 0.04746 -0.00511 0.00009 0.00366 C6 1 0.278387 0.353530 0.492766 11.00000 0.06226 0.05599 = 0.04493 -0.00110 0.00097 0.00220 C7 1 0.176490 0.349508 0.507742 11.00000 0.06907 0.06001 = 0.05066 0.00287 0.00663 -0.00057 C8 1 0.133739 0.617150 0.545533 11.00000 0.07459 0.05277 = 0.05674 0.00187 -0.00599 -0.00339 C9 1 0.226510 0.600580 0.534587 11.00000 0.06934 0.07285 = 0.07686 -0.00288 -0.01275 0.00004 AFIX 43 H9 2 0.271184 0.601030 0.562322 11.00000 -1.20000 AFIX 0 C10 1 0.253986 0.582876 0.481246 11.00000 0.06372 0.07258 = 0.08720 -0.00330 0.00387 0.00039 AFIX 43 H10 2 0.317570 0.571695 0.473641 11.00000 -1.20000 AFIX 0 C11 1 0.190780 0.581608 0.440655 11.00000 0.06775 0.06753 = 0.06560 -0.00322 0.01130 -0.00389 AFIX 43 H11 2 0.210421 0.569869 0.405279 11.00000 -1.20000 AFIX 0 C12 1 0.094911 0.598111 0.451972 11.00000 0.06340 0.05331 = 0.05622 0.00046 0.00453 -0.00363 C13 1 0.094259 0.637788 0.599940 11.00000 0.10084 0.07900 = 0.05367 0.00032 -0.00497 0.00219 AFIX 137 H13A 2 0.144791 0.640273 0.625976 11.00000 -1.50000 H13B 2 0.050404 0.588790 0.609938 11.00000 -1.50000 H13C 2 0.061996 0.697675 0.599165 11.00000 -1.50000 AFIX 0 N1 3 0.070216 0.615237 0.504021 11.00000 0.06123 0.05707 = 0.04983 0.00075 0.00377 -0.00175 AFIX 43 H1B 2 0.011469 0.625427 0.511261 11.00000 -1.20000 AFIX 0 N2 3 0.027710 0.596730 0.414797 11.00000 0.06805 0.10366 = 0.05146 -0.00411 0.00517 -0.00382 AFIX 93 H2A 2 -0.030288 0.606596 0.423918 11.00000 -1.20000 H2B 2 0.041888 0.585963 0.381435 11.00000 -1.20000 AFIX 0 O1 4 0.244644 0.350815 0.397471 11.00000 0.07451 0.13012 = 0.04794 -0.01131 -0.00302 0.00206 O2 4 0.115779 0.351002 0.469628 11.00000 0.05954 0.09347 = 0.05987 -0.00286 -0.00139 -0.00337 O3 4 0.154382 0.346654 0.556723 11.00000 0.07906 0.12170 = 0.05357 0.01693 0.01311 0.00500 H1A 2 0.191246 0.350710 0.412098 11.00000 0.10330 HKLF 4 REM J in I4(1)/a REM R1 = 0.0546 for 1564 Fo > 4sig(Fo) and 0.1063 for all 2705 data REM 169 parameters refined using 1 restraints END WGHT 0.0790 4.2474 REM Highest difference peak 0.169, deepest hole -0.177, 1-sigma level 0.039 Q1 1 -0.0429 0.6419 0.5158 11.00000 0.05 0.17 Q2 1 0.2772 0.3815 0.4915 11.00000 0.05 0.14 Q3 1 0.0001 0.6423 0.6002 11.00000 0.05 0.14 Q4 1 0.0853 0.3807 0.5214 11.00000 0.05 0.14 Q5 1 -0.0632 0.6488 0.4325 11.00000 0.05 0.14 Q6 1 0.1224 0.7142 0.6227 11.00000 0.05 0.14 Q7 1 0.0994 0.6073 0.6438 11.00000 0.05 0.14 Q8 1 0.0937 0.6385 0.3557 11.00000 0.05 0.14 Q9 1 0.0956 0.4099 0.5208 11.00000 0.05 0.14 Q10 1 0.4250 0.3885 0.5199 11.00000 0.05 0.13 Q11 1 0.1583 0.3924 0.6021 11.00000 0.05 0.13 Q12 1 -0.0752 0.6635 0.4419 11.00000 0.05 0.13 Q13 1 0.3174 0.3716 0.5827 11.00000 0.05 0.13 Q14 1 0.4196 0.3986 0.3760 11.00000 0.05 0.13 Q15 1 0.1531 0.3699 0.5560 11.00000 0.05 0.13 Q16 1 0.3040 0.3306 0.5780 11.00000 0.05 0.13 Q17 1 0.0391 0.3155 0.4427 11.00000 0.05 0.13 Q18 1 0.1195 0.6250 0.5221 11.00000 0.05 0.13 Q19 1 0.4094 0.3577 0.5810 11.00000 0.05 0.13 Q20 1 0.0563 0.4119 0.4365 11.00000 0.05 0.12 Q21 1 0.2763 0.3497 0.3464 11.00000 0.05 0.12 Q22 1 0.3947 0.3295 0.6256 11.00000 0.05 0.12 Q23 1 0.3449 0.5769 0.6066 11.00000 0.05 0.12 Q24 1 0.3443 0.6378 0.4688 11.00000 0.05 0.12 Q25 1 0.4963 0.3154 0.5495 11.00000 0.05 0.12 ; _cod_data_source_file bt4008sup1.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'I 41/a' _cod_database_code 1543275 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' '-y+3/4, x+1/4, z+1/4' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1, z+1/2' '-y+5/4, x+3/4, z+3/4' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'x, y-1/2, -z' 'y-3/4, -x-1/4, -z-1/4' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' '-y+1/4, x+1/4, -z+1/4' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity C C1 0.3466(2) 0.3614(2) 0.53227(11) 0.0800(9) Uani d . 1 1 H H1 0.3287 0.3597 0.5686 0.096 Uiso calc R 1 1 C C2 0.4403(2) 0.3718(3) 0.51924(13) 0.1165(15) Uani d . 1 1 H H2 0.4854 0.3779 0.5465 0.140 Uiso calc R 1 1 C C3 0.4674(2) 0.3733(3) 0.46571(13) 0.1088(13) Uani d . 1 1 H H3 0.5311 0.3798 0.4568 0.131 Uiso calc R 1 1 C C4 0.4020(2) 0.3655(2) 0.42581(12) 0.0780(8) Uani d . 1 1 H H4 0.4210 0.3666 0.3897 0.094 Uiso calc R 1 1 C C5 0.30732(18) 0.35571(17) 0.43851(9) 0.0585(6) Uani d . 1 1 C C6 0.27839(17) 0.35353(16) 0.49277(9) 0.0544(6) Uani d . 1 1 C C7 0.17649(18) 0.34951(17) 0.50774(10) 0.0599(6) Uani d . 1 1 C C8 0.13374(19) 0.61715(17) 0.54553(10) 0.0614(6) Uani d . 1 1 C C9 0.2265(2) 0.6006(2) 0.53459(12) 0.0730(7) Uani d . 1 1 H H9 0.2712 0.6010 0.5623 0.088 Uiso calc R 1 1 C C10 0.2540(2) 0.5829(2) 0.48125(12) 0.0745(8) Uani d . 1 1 H H10 0.3176 0.5717 0.4736 0.089 Uiso calc R 1 1 C C11 0.19078(19) 0.58161(18) 0.44066(11) 0.0670(7) Uani d . 1 1 H H11 0.2104 0.5699 0.4053 0.080 Uiso calc R 1 1 C C12 0.09491(17) 0.59811(17) 0.45197(10) 0.0576(6) Uani d . 1 1 C C13 0.0943(2) 0.6378(2) 0.59994(11) 0.0778(8) Uani d . 1 1 H H13A 0.1448 0.6403 0.6260 0.117 Uiso calc R 1 1 H H13B 0.0504 0.5888 0.6099 0.117 Uiso calc R 1 1 H H13C 0.0620 0.6977 0.5992 0.117 Uiso calc R 1 1 N N1 0.07022(14) 0.61524(13) 0.50402(7) 0.0560(5) Uani d . 1 1 H H1B 0.0115 0.6254 0.5113 0.067 Uiso calc R 1 1 N N2 0.02771(16) 0.59673(17) 0.41480(8) 0.0744(7) Uani d . 1 1 H H2A -0.0303 0.6066 0.4239 0.089 Uiso calc R 1 1 H H2B 0.0419 0.5860 0.3814 0.089 Uiso calc R 1 1 O O1 0.24464(16) 0.35081(17) 0.39747(7) 0.0842(6) Uani d D 1 1 O O2 0.11578(12) 0.35100(14) 0.46963(7) 0.0710(5) Uani d . 1 1 O O3 0.15438(14) 0.34665(16) 0.55672(7) 0.0848(6) Uani d . 1 1 H H1A 0.1912(12) 0.351(3) 0.4121(13) 0.103(12) Uiso d D 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0703(18) 0.121(3) 0.0491(14) 0.0083(16) -0.0032(13) -0.0042(15) C2 0.068(2) 0.210(5) 0.071(2) 0.003(2) -0.0143(16) -0.015(2) C3 0.0611(18) 0.187(4) 0.078(2) -0.001(2) 0.0049(16) -0.021(2) C4 0.0699(18) 0.105(2) 0.0590(16) 0.0030(15) 0.0115(13) -0.0068(15) C5 0.0649(15) 0.0631(14) 0.0475(12) 0.0037(11) 0.0001(11) -0.0051(11) C6 0.0623(14) 0.0560(13) 0.0449(12) 0.0022(10) 0.0010(10) -0.0011(10) C7 0.0691(16) 0.0600(14) 0.0507(13) -0.0006(11) 0.0066(12) 0.0029(11) C8 0.0746(17) 0.0528(13) 0.0567(14) -0.0034(11) -0.0060(12) 0.0019(11) C9 0.0693(17) 0.0729(17) 0.0769(18) 0.0000(13) -0.0128(14) -0.0029(14) C10 0.0637(16) 0.0726(18) 0.087(2) 0.0004(13) 0.0039(15) -0.0033(15) C11 0.0678(16) 0.0675(16) 0.0656(15) -0.0039(12) 0.0113(13) -0.0032(12) C12 0.0634(15) 0.0533(13) 0.0562(14) -0.0036(11) 0.0045(11) 0.0005(10) C13 0.101(2) 0.0790(19) 0.0537(15) 0.0022(15) -0.0050(14) 0.0003(13) N1 0.0612(12) 0.0571(11) 0.0498(11) -0.0018(8) 0.0038(9) 0.0008(9) N2 0.0680(14) 0.1037(18) 0.0515(12) -0.0038(12) 0.0052(10) -0.0041(11) O1 0.0745(14) 0.1301(18) 0.0479(10) 0.0021(12) -0.0030(10) -0.0113(11) O2 0.0595(11) 0.0935(14) 0.0599(11) -0.0034(9) -0.0014(8) -0.0029(9) O3 0.0791(13) 0.1217(17) 0.0536(11) 0.0050(11) 0.0131(9) 0.0169(10) 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 C2 C1 C6 121.3(3) C2 C1 H1 119.4 C6 C1 H1 119.4 C1 C2 C3 119.7(3) C1 C2 H2 120.1 C3 C2 H2 120.1 C4 C3 C2 120.5(3) C4 C3 H3 119.8 C2 C3 H3 119.7 C3 C4 C5 120.2(3) C3 C4 H4 119.9 C5 C4 H4 119.9 O1 C5 C4 118.1(2) O1 C5 C6 121.7(2) C4 C5 C6 120.1(2) C1 C6 C5 118.1(2) C1 C6 C7 120.3(2) C5 C6 C7 121.4(2) O3 C7 O2 123.2(2) O3 C7 C6 118.9(2) O2 C7 C6 117.9(2) C9 C8 N1 118.8(2) C9 C8 C13 125.2(3) N1 C8 C13 115.9(2) C8 C9 C10 119.1(3) C8 C9 H9 120.4 C10 C9 H9 120.4 C11 C10 C9 121.4(3) C11 C10 H10 119.3 C9 C10 H10 119.3 C10 C11 C12 119.4(3) C10 C11 H11 120.3 C12 C11 H11 120.3 N2 C12 N1 118.5(2) N2 C12 C11 123.6(2) N1 C12 C11 117.9(2) C8 C13 H13A 109.5 C8 C13 H13B 109.5 H13A C13 H13B 109.5 C8 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C12 N1 C8 123.2(2) C12 N1 H1B 118.4 C8 N1 H1B 118.4 C12 N2 H2A 120.0 C12 N2 H2B 120.0 H2A N2 H2B 120.0 C5 O1 H1A 106(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.368(4) C1 C6 1.374(3) C1 H1 0.9300 C2 C3 1.374(4) C2 H2 0.9300 C3 C4 1.353(4) C3 H3 0.9300 C4 C5 1.379(4) C4 H4 0.9300 C5 O1 1.346(3) C5 C6 1.399(3) C6 C7 1.485(3) C7 O3 1.248(3) C7 O2 1.272(3) C8 C9 1.357(4) C8 N1 1.361(3) C8 C13 1.481(4) C9 C10 1.394(4) C9 H9 0.9300 C10 C11 1.341(4) C10 H10 0.9300 C11 C12 1.401(4) C11 H11 0.9300 C12 N2 1.319(3) C12 N1 1.351(3) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 N1 H1B 0.8600 N2 H2A 0.8600 N2 H2B 0.8600 O1 H1A 0.835(10) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1A O2 . 0.835(10) 1.774(18) 2.544(3) 152(3) y N1 H1B O2 9_566 0.86 1.89 2.745(3) 177 y N2 H2A O3 9_566 0.86 1.93 2.781(3) 169 y N2 H2B O3 8_454 0.86 2.00 2.836(3) 163 y 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 C6 C1 C2 C3 -0.8(6) C1 C2 C3 C4 0.6(7) C2 C3 C4 C5 -0.1(6) C3 C4 C5 O1 178.2(3) C3 C4 C5 C6 -0.2(4) C2 C1 C6 C5 0.4(5) C2 C1 C6 C7 -175.4(3) O1 C5 C6 C1 -178.3(3) C4 C5 C6 C1 0.1(4) O1 C5 C6 C7 -2.4(4) C4 C5 C6 C7 175.9(2) C1 C6 C7 O3 -5.0(4) C5 C6 C7 O3 179.2(2) C1 C6 C7 O2 173.6(3) C5 C6 C7 O2 -2.1(3) N1 C8 C9 C10 0.5(4) C13 C8 C9 C10 -179.4(3) C8 C9 C10 C11 -0.2(4) C9 C10 C11 C12 -0.2(4) C10 C11 C12 N2 -178.9(3) C10 C11 C12 N1 0.3(4) N2 C12 N1 C8 179.2(2) C11 C12 N1 C8 0.0(3) C9 C8 N1 C12 -0.4(4) C13 C8 N1 C12 179.5(2) _cod_database_fobs_code 1543275