#------------------------------------------------------------------------------ #$Date: 2014-11-22 15:20:09 +0200 (Sat, 22 Nov 2014) $ #$Revision: 127815 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/24/4512412.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_4512412 loop_ _publ_author_name 'Surov, Artem O.' 'Simagina, Anna A.' 'Manin, Nikolay G.' 'Kuzmina, Lyudmila G.' 'Churakov, Andrei V.' 'Perlovich, German L.' _publ_section_title ; Fenamate Cocrystals with 4,4′-Bipyridine: Structural and Thermodynamic Aspects ; _journal_name_full 'Crystal Growth & Design' _journal_page_first 141121144825007 _journal_paper_doi 10.1021/cg5012633 _journal_year 2014 _chemical_formula_moiety '2(C14 H12 Cl N O2), C10 H8 N2' _chemical_formula_sum 'C38 H32 Cl2 N4 O4' _chemical_formula_weight 679.58 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 106.911(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 4.7315(12) _cell_length_b 45.263(12) _cell_length_c 7.929(2) _cell_measurement_reflns_used 6181 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 28.261 _cell_measurement_theta_min 2.700 _cell_volume 1624.7(7) _computing_cell_refinement 'SAINT (Bruker, 2008)' _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 183(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART APEX II' _diffrn_measurement_method \w _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 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 57 _diffrn_reflns_limit_k_min -57 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 13525 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.80 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_T_max 0.9755 _exptl_absorpt_correction_T_min 0.9404 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2008)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 708 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.230 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 3508 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.142 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0493 _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^)+(0.0268P)^2^+1.1587P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1054 _refine_ls_wR_factor_ref 0.1086 _reflns_number_gt 3094 _reflns_number_total 3508 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL TFA-BP in P2(1)/c CELL 0.71073 4.7315 45.2630 7.9286 90.000 106.911 90.000 ZERR 2.00 0.0012 0.0115 0.0020 0.000 0.003 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O CL UNIT 76 64 8 8 4 TEMP -90 SIZE .25 .20 .10 EQIV $1 1+X, Y, Z HTAB N1 O1 HTAB O2 N2_$1 L.S. 10 BOND $H ACTA CONF FMAP 2 PLAN 6 OMIT -2 54 OMIT 0 2 0 WGHT 0.026800 1.158700 FVAR 0.17601 CL1 5 0.366884 0.246345 0.340102 11.00000 0.05780 0.03520 = 0.05335 0.00507 0.00645 -0.00043 N1 3 0.539873 0.359224 0.382104 11.00000 0.04951 0.03874 = 0.03262 -0.00616 0.02150 -0.01254 O1 4 0.859601 0.405355 0.337537 11.00000 0.06607 0.03702 = 0.03923 -0.00539 0.02033 -0.01218 O2 4 0.989937 0.438819 0.551525 11.00000 0.07083 0.03716 = 0.05214 -0.01283 0.01539 -0.01223 C11 1 0.723935 0.397340 0.600876 11.00000 0.04054 0.03133 = 0.03007 -0.00151 0.00595 0.00969 C12 1 0.558964 0.371321 0.543048 11.00000 0.03526 0.03664 = 0.02918 0.00026 0.00995 0.00779 C13 1 0.414592 0.358122 0.655890 11.00000 0.04337 0.05014 = 0.03612 0.00169 0.01771 0.00642 C14 1 0.442101 0.369465 0.820237 11.00000 0.06250 0.05569 = 0.03636 0.00783 0.02519 0.01971 C15 1 0.614384 0.394060 0.881054 11.00000 0.07862 0.05421 = 0.02586 -0.00002 0.01402 0.02949 C16 1 0.750268 0.407780 0.771679 11.00000 0.05989 0.03683 = 0.03354 -0.00455 0.00328 0.01681 C17 1 0.863221 0.413514 0.484821 11.00000 0.04153 0.03035 = 0.04075 -0.00372 0.00518 0.00211 C21 1 0.364509 0.334378 0.307131 11.00000 0.03717 0.03641 = 0.02799 -0.00416 0.01589 -0.00499 C22 1 0.109901 0.339229 0.168731 11.00000 0.04850 0.03936 = 0.03343 0.00199 0.01419 0.00552 C23 1 -0.057964 0.315872 0.083764 11.00000 0.04146 0.04899 = 0.03607 -0.00243 0.00088 0.00663 C24 1 0.023523 0.287358 0.138233 11.00000 0.03891 0.04128 = 0.03886 -0.00826 0.00592 -0.00531 C25 1 0.274923 0.282815 0.276869 11.00000 0.03624 0.03427 = 0.03433 0.00128 0.01270 0.00085 C26 1 0.453699 0.305658 0.365696 11.00000 0.03035 0.03756 = 0.03036 0.00090 0.01428 -0.00196 C27 1 0.727356 0.299794 0.514570 11.00000 0.03413 0.04863 = 0.04176 0.00119 0.00653 -0.00187 N2 3 0.186271 0.467247 0.310701 11.00000 0.04675 0.03587 = 0.06670 -0.00320 0.00940 -0.00741 C1 1 0.243950 0.496136 0.312361 11.00000 0.06528 0.03682 = 0.06872 -0.01270 0.01970 -0.00823 C2 1 0.366918 0.509481 0.195358 11.00000 0.06252 0.02694 = 0.06884 -0.00827 0.01620 -0.00747 C3 1 0.433691 0.493254 0.064964 11.00000 0.02800 0.02817 = 0.06587 -0.00349 0.00299 -0.00158 C4 1 0.369310 0.463307 0.061867 11.00000 0.07078 0.02883 = 0.09623 -0.01238 0.04289 -0.00874 C5 1 0.250056 0.451410 0.184340 11.00000 0.06092 0.03078 = 0.09020 -0.00743 0.03056 -0.00741 H11 2 0.617485 0.369261 0.320185 11.00000 0.04398 H21 2 1.050393 0.447683 0.474831 11.00000 0.06702 H1 2 0.186301 0.507356 0.400707 11.00000 0.08040 H2 2 0.404005 0.529923 0.205037 11.00000 0.06001 H4 2 0.407276 0.451675 -0.019659 11.00000 0.08043 H5 2 0.219409 0.430409 0.186590 11.00000 0.07469 H13 2 0.293492 0.341401 0.612052 11.00000 0.05382 H14 2 0.345124 0.361172 0.894319 11.00000 0.05224 H15 2 0.639197 0.401851 0.994038 11.00000 0.06451 H16 2 0.874563 0.424422 0.813502 11.00000 0.04532 H22 2 0.059989 0.359500 0.130498 11.00000 0.04799 H23 2 -0.236461 0.319589 -0.009613 11.00000 0.04582 H24 2 -0.084942 0.271432 0.084975 11.00000 0.04434 H27A 2 0.672598 0.290691 0.611225 11.00000 0.08469 H27B 2 0.856097 0.285884 0.480403 11.00000 0.06963 H27C 2 0.832219 0.316745 0.554067 11.00000 0.07042 HKLF 4 REM z in P2(1)/c REM R1 = 0.0493 for 3094 Fo > 4sig(Fo) and 0.0567 for all 3508 data REM 281 parameters refined using 0 restraints END WGHT 0.0268 1.1587 REM Highest difference peak 0.230, deepest hole -0.235, 1-sigma level 0.040 Q1 1 0.7092 0.3819 0.5828 11.00000 0.05 0.23 Q2 1 0.4522 0.3197 0.2948 11.00000 0.05 0.19 Q3 1 0.3155 0.4551 0.2867 11.00000 0.05 0.18 Q4 1 0.1158 0.2863 0.2490 11.00000 0.05 0.17 Q5 1 0.3798 0.3197 0.3592 11.00000 0.05 0.17 Q6 1 0.3344 0.2953 0.3554 11.00000 0.05 0.17 ; _[local]_cod_data_source_file cg5012633_si_006.cif _[local]_cod_data_source_block TFA-BP _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 1624.6(7) _cod_database_code 4512412 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_symmetry_multiplicity _atom_site_calc_flag Cl1 Cl 0.36688(14) 0.246345(12) 0.34010(8) 0.05084(18) Uani 1 1 d N1 N 0.5399(4) 0.35922(4) 0.3821(2) 0.0383(4) Uani 1 1 d O1 O 0.8596(4) 0.40535(3) 0.33754(19) 0.0464(4) Uani 1 1 d O2 O 0.9899(4) 0.43882(4) 0.5515(2) 0.0539(4) Uani 1 1 d C11 C 0.7239(4) 0.39734(4) 0.6009(2) 0.0349(4) Uani 1 1 d C12 C 0.5590(4) 0.37132(4) 0.5430(2) 0.0336(4) Uani 1 1 d C13 C 0.4146(5) 0.35812(5) 0.6559(3) 0.0419(5) Uani 1 1 d C14 C 0.4421(6) 0.36947(6) 0.8202(3) 0.0492(6) Uani 1 1 d C15 C 0.6144(6) 0.39406(6) 0.8811(3) 0.0531(7) Uani 1 1 d C16 C 0.7503(6) 0.40778(5) 0.7717(3) 0.0456(5) Uani 1 1 d C17 C 0.8632(5) 0.41351(4) 0.4848(3) 0.0390(5) Uani 1 1 d C21 C 0.3645(4) 0.33438(4) 0.3071(2) 0.0325(4) Uani 1 1 d C22 C 0.1099(5) 0.33923(5) 0.1687(3) 0.0400(5) Uani 1 1 d C23 C -0.0580(5) 0.31587(5) 0.0838(3) 0.0444(5) Uani 1 1 d C24 C 0.0235(5) 0.28736(5) 0.1382(3) 0.0408(5) Uani 1 1 d C25 C 0.2749(4) 0.28282(4) 0.2769(3) 0.0344(4) Uani 1 1 d C26 C 0.4537(4) 0.30566(4) 0.3657(2) 0.0316(4) Uani 1 1 d C27 C 0.7274(5) 0.29979(6) 0.5146(3) 0.0425(5) Uani 1 1 d N2 N 0.1863(4) 0.46725(4) 0.3107(3) 0.0513(5) Uani 1 1 d C1 C 0.2439(6) 0.49614(5) 0.3124(4) 0.0569(6) Uani 1 1 d C2 C 0.3669(6) 0.50948(5) 0.1954(4) 0.0534(6) Uani 1 1 d C3 C 0.4337(4) 0.49325(4) 0.0650(3) 0.0429(5) Uani 1 1 d C4 C 0.3693(6) 0.46331(5) 0.0619(4) 0.0613(7) Uani 1 1 d C5 C 0.2501(6) 0.45141(5) 0.1843(4) 0.0588(7) Uani 1 1 d H11 H 0.617(5) 0.3693(5) 0.320(3) 0.044(6) Uiso 1 1 d H21 H 1.050(6) 0.4477(6) 0.475(4) 0.067(9) Uiso 1 1 d H1 H 0.186(7) 0.5074(7) 0.401(4) 0.080(9) Uiso 1 1 d H2 H 0.404(6) 0.5299(6) 0.205(3) 0.060(7) Uiso 1 1 d H4 H 0.407(7) 0.4517(7) -0.020(4) 0.080(10) Uiso 1 1 d H5 H 0.219(6) 0.4304(6) 0.187(4) 0.075(9) Uiso 1 1 d H13 H 0.293(6) 0.3414(6) 0.612(3) 0.054(7) Uiso 1 1 d H14 H 0.345(5) 0.3612(5) 0.894(3) 0.052(7) Uiso 1 1 d H15 H 0.639(6) 0.4019(6) 0.994(4) 0.065(8) Uiso 1 1 d H16 H 0.875(5) 0.4244(5) 0.814(3) 0.045(6) Uiso 1 1 d H22 H 0.060(5) 0.3595(5) 0.130(3) 0.048(6) Uiso 1 1 d H23 H -0.236(5) 0.3196(5) -0.010(3) 0.046(6) Uiso 1 1 d H24 H -0.085(5) 0.2714(5) 0.085(3) 0.044(6) Uiso 1 1 d H27A H 0.673(7) 0.2907(7) 0.611(4) 0.085(10) Uiso 1 1 d H27B H 0.856(6) 0.2859(6) 0.480(4) 0.070(8) Uiso 1 1 d H27C H 0.832(6) 0.3167(6) 0.554(4) 0.070(9) 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 0.0578(4) 0.0352(3) 0.0534(3) 0.0051(2) 0.0065(3) -0.0004(2) N1 0.0495(11) 0.0387(9) 0.0326(9) -0.0062(7) 0.0215(8) -0.0125(8) O1 0.0661(10) 0.0370(8) 0.0392(8) -0.0054(6) 0.0203(7) -0.0122(7) O2 0.0708(12) 0.0372(9) 0.0521(10) -0.0128(7) 0.0154(9) -0.0122(8) C11 0.0405(11) 0.0313(10) 0.0301(9) -0.0015(8) 0.0059(8) 0.0097(8) C12 0.0353(10) 0.0366(10) 0.0292(9) 0.0003(8) 0.0100(8) 0.0078(8) C13 0.0434(12) 0.0501(13) 0.0361(11) 0.0017(9) 0.0177(9) 0.0064(10) C14 0.0625(15) 0.0557(14) 0.0364(11) 0.0078(10) 0.0252(11) 0.0197(12) C15 0.0786(18) 0.0542(14) 0.0259(10) 0.0000(10) 0.0140(11) 0.0295(13) C16 0.0599(15) 0.0368(11) 0.0335(11) -0.0046(9) 0.0033(10) 0.0168(10) C17 0.0415(11) 0.0303(10) 0.0408(11) -0.0037(8) 0.0052(9) 0.0021(8) C21 0.0372(10) 0.0364(10) 0.0280(9) -0.0042(7) 0.0159(8) -0.0050(8) C22 0.0485(12) 0.0394(11) 0.0334(10) 0.0020(9) 0.0142(9) 0.0055(10) C23 0.0415(12) 0.0490(13) 0.0361(11) -0.0024(9) 0.0009(9) 0.0066(10) C24 0.0389(11) 0.0413(11) 0.0389(11) -0.0083(9) 0.0059(9) -0.0053(9) C25 0.0362(10) 0.0343(10) 0.0343(10) 0.0013(8) 0.0127(8) 0.0009(8) C26 0.0303(10) 0.0376(10) 0.0304(9) 0.0009(8) 0.0143(8) -0.0020(8) C27 0.0341(11) 0.0486(13) 0.0418(12) 0.0012(10) 0.0065(9) -0.0019(10) N2 0.0467(11) 0.0359(10) 0.0667(13) -0.0032(9) 0.0094(10) -0.0074(8) C1 0.0653(16) 0.0368(12) 0.0687(17) -0.0127(12) 0.0197(13) -0.0082(11) C2 0.0625(15) 0.0269(10) 0.0688(16) -0.0083(10) 0.0162(13) -0.0075(10) C3 0.0280(10) 0.0282(10) 0.0659(14) -0.0035(9) 0.0030(9) -0.0016(8) C4 0.0708(18) 0.0288(11) 0.096(2) -0.0124(13) 0.0429(16) -0.0087(11) C5 0.0609(16) 0.0308(11) 0.090(2) -0.0074(12) 0.0306(14) -0.0074(11) 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 _geom_angle_site_symmetry_3 C12 N1 C21 125.41(17) . C12 N1 H11 114.4(16) . C21 N1 H11 119.4(16) . C17 O2 H21 109(2) . C16 C11 C12 118.6(2) . C16 C11 C17 120.3(2) . C12 C11 C17 121.11(17) . N1 C12 C13 120.73(19) . N1 C12 C11 121.11(18) . C13 C12 C11 118.16(18) . C14 C13 C12 121.1(2) . C14 C13 H13 121.7(15) . C12 C13 H13 117.2(15) . C13 C14 C15 121.1(2) . C13 C14 H14 121.7(16) . C15 C14 H14 117.2(15) . C16 C15 C14 118.9(2) . C16 C15 H15 118.9(17) . C14 C15 H15 122.3(17) . C15 C16 C11 122.1(2) . C15 C16 H16 119.6(14) . C11 C16 H16 118.3(14) . O1 C17 O2 121.4(2) . O1 C17 C11 124.27(18) . O2 C17 C11 114.31(19) . C22 C21 C26 121.02(18) . C22 C21 N1 118.13(18) . C26 C21 N1 120.79(18) . C23 C22 C21 120.6(2) . C23 C22 H22 121.3(14) . C21 C22 H22 118.1(14) . C22 C23 C24 119.8(2) . C22 C23 H23 119.7(14) . C24 C23 H23 120.5(14) . C23 C24 C25 119.1(2) . C23 C24 H24 121.7(14) . C25 C24 H24 119.2(14) . C24 C25 C26 123.29(19) . C24 C25 Cl1 117.09(16) . C26 C25 Cl1 119.62(15) . C25 C26 C21 116.17(17) . C25 C26 C27 121.70(19) . C21 C26 C27 122.13(18) . C26 C27 H27A 109.2(19) . C26 C27 H27B 111.4(17) . H27A C27 H27B 106(2) . C26 C27 H27C 112.2(18) . H27A C27 H27C 109(2) . H27B C27 H27C 109(2) . C1 N2 C5 116.3(2) . N2 C1 C2 123.4(2) . N2 C1 H1 114.9(18) . C2 C1 H1 121.6(18) . C1 C2 C3 120.5(2) . C1 C2 H2 119.0(16) . C3 C2 H2 120.5(16) . C2 C3 C4 115.9(2) . C2 C3 C3 122.5(2) 3_665 C4 C3 C3 121.6(3) 3_665 C5 C4 C3 120.4(3) . C5 C4 H4 120(2) . C3 C4 H4 120(2) . N2 C5 C4 123.4(2) . N2 C5 H5 116.6(17) . C4 C5 H5 119.8(17) . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cl1 C25 1.743(2) . N1 C12 1.367(2) . N1 C21 1.421(2) . N1 H11 0.83(2) . O1 C17 1.220(2) . O2 C17 1.329(2) . O2 H21 0.84(3) . C11 C16 1.405(3) . C11 C12 1.414(3) . C11 C17 1.473(3) . C12 C13 1.407(3) . C13 C14 1.371(3) . C13 H13 0.95(3) . C14 C15 1.381(4) . C14 H14 0.92(3) . C15 C16 1.369(4) . C15 H15 0.94(3) . C16 H16 0.95(2) . C21 C22 1.391(3) . C21 C26 1.403(3) . C22 C23 1.375(3) . C22 H22 0.97(2) . C23 C24 1.380(3) . C23 H23 0.96(2) . C24 C25 1.380(3) . C24 H24 0.91(2) . C25 C26 1.391(3) . C26 C27 1.500(3) . C27 H27A 0.97(3) . C27 H27B 0.97(3) . C27 H27C 0.92(3) . N2 C1 1.335(3) . N2 C5 1.336(3) . C1 C2 1.370(4) . C1 H1 0.97(3) . C2 C3 1.378(3) . C2 H2 0.94(3) . C3 C4 1.388(3) . C3 C3 1.485(5) 3_665 C4 C5 1.367(4) . C4 H4 0.89(3) . C5 H5 0.96(3) . 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 H11 O1 0.83(2) 1.98(2) 2.662(2) 139(2) . O2 H21 N2 0.84(3) 1.84(3) 2.683(3) 179(3) 1_655 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_4 C21 N1 C12 C13 4.5(3) . . C21 N1 C12 C11 -175.54(19) . . C16 C11 C12 N1 -176.25(19) . . C17 C11 C12 N1 4.5(3) . . C16 C11 C12 C13 3.7(3) . . C17 C11 C12 C13 -175.61(18) . . N1 C12 C13 C14 177.4(2) . . C11 C12 C13 C14 -2.5(3) . . C12 C13 C14 C15 -0.6(3) . . C13 C14 C15 C16 2.4(4) . . C14 C15 C16 C11 -1.1(3) . . C12 C11 C16 C15 -2.0(3) . . C17 C11 C16 C15 177.3(2) . . C16 C11 C17 O1 177.2(2) . . C12 C11 C17 O1 -3.5(3) . . C16 C11 C17 O2 -4.6(3) . . C12 C11 C17 O2 174.67(18) . . C12 N1 C21 C22 106.7(2) . . C12 N1 C21 C26 -76.3(3) . . C26 C21 C22 C23 -1.2(3) . . N1 C21 C22 C23 175.82(19) . . C21 C22 C23 C24 1.2(3) . . C22 C23 C24 C25 -0.5(3) . . C23 C24 C25 C26 -0.2(3) . . C23 C24 C25 Cl1 179.94(17) . . C24 C25 C26 C21 0.2(3) . . Cl1 C25 C26 C21 -179.90(14) . . C24 C25 C26 C27 -179.3(2) . . Cl1 C25 C26 C27 0.6(3) . . C22 C21 C26 C25 0.4(3) . . N1 C21 C26 C25 -176.47(17) . . C22 C21 C26 C27 179.96(19) . . N1 C21 C26 C27 3.0(3) . . C5 N2 C1 C2 -1.2(4) . . N2 C1 C2 C3 1.2(4) . . C1 C2 C3 C4 -0.1(4) . . C1 C2 C3 C3 179.8(3) . 3_665 C2 C3 C4 C5 -0.7(4) . . C3 C3 C4 C5 179.3(3) 3_665 . C1 N2 C5 C4 0.3(4) . . C3 C4 C5 N2 0.6(5) . .