#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013216.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_2013216 loop_ _publ_author_name 'Bowes, Katharine F.' 'Ferguson, George' 'Lough, Alan J.' 'Glidewell, Christopher' _publ_section_title ;meso-5,5,7,12,12,14-Hexamethyl-1,4-diaza-8,11-diazoniacyclotetradecane bis(2-naphthoate) ethanol disolvate: centrosymmetric five-component aggregates linked into sheets by C---H···\p(arene) hydrogen bonding ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o147 _journal_page_last o149 _journal_paper_doi 10.1107/S0108270103002804 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C16 H38 N4 2+ , 2C11 H7 O2 - , 2C2 H6 O' _chemical_formula_sum 'C42 H64 N4 O6' _chemical_formula_weight 720.97 _chemical_name_systematic ; Meso-5,5,7,12,12,14-hexamethyl-1,4-diaza-8,11-diazoniumcyclotetradecane bis(2-naphthoate) ethanol disolvate ; _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 101.446(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.9563(4) _cell_length_b 10.9584(5) _cell_length_c 17.1665(8) _cell_measurement_reflns_used 4606 _cell_measurement_temperature 150.0(10) _cell_measurement_theta_max 27.50 _cell_measurement_theta_min 2.76 _cell_volume 2020.08(15) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150.0(10) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.075 _diffrn_reflns_av_sigmaI/netI 0.062 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 17192 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.76 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.16 _refine_diff_density_min -0.17 _refine_ls_extinction_coef 0.014(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 241 _refine_ls_number_reflns 4606 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.082 _refine_ls_R_factor_gt 0.048 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.3194P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.112 _refine_ls_wR_factor_ref 0.130 _reflns_number_gt 3130 _reflns_number_total 4606 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1618.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2013216 _cod_database_fobs_code 2013216 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_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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.59018(11) 0.52392(11) 0.61507(7) 0.0312(3) Uani d . 1 . . N C2 0.57058(15) 0.39781(14) 0.64207(9) 0.0356(4) Uani d . 1 . . C C3 0.43695(15) 0.35860(15) 0.61481(9) 0.0370(4) Uani d . 1 . . C N4 0.40393(11) 0.35695(11) 0.52786(7) 0.0325(3) Uani d . 1 . . N C5 0.27070(14) 0.33163(15) 0.49161(9) 0.0361(4) Uani d . 1 . . C C51 0.22189(17) 0.21533(17) 0.52546(11) 0.0480(4) Uani d . 1 . . C C52 0.19147(15) 0.44189(17) 0.50605(10) 0.0439(4) Uani d . 1 . . C C6 0.26297(15) 0.31186(15) 0.40202(9) 0.0368(4) Uani d . 1 . . C C7 0.28454(14) 0.42168(15) 0.35181(9) 0.0348(4) Uani d . 1 . . C C71 0.27610(16) 0.38570(16) 0.26513(9) 0.0429(4) Uani d . 1 . . C O1 0.41503(11) 0.66378(11) 0.65109(7) 0.0457(3) Uani d . 1 . . O O2 0.37126(11) 0.75854(11) 0.53397(7) 0.0440(3) Uani d . 1 . . O C11 0.21341(14) 0.76163(13) 0.70018(9) 0.0320(3) Uani d . 1 . . C C12 0.23857(13) 0.79095(13) 0.62741(9) 0.0310(3) Uani d . 1 . . C C13 0.16199(14) 0.87711(15) 0.57892(9) 0.0365(4) Uani d . 1 . . C C14 0.06376(14) 0.93073(15) 0.60461(9) 0.0385(4) Uani d . 1 . . C C15 -0.06156(15) 0.95855(16) 0.70949(11) 0.0430(4) Uani d . 1 . . C C16 -0.07952(16) 0.93351(17) 0.78424(11) 0.0466(4) Uani d . 1 . . C C17 -0.00250(16) 0.84944(16) 0.83312(10) 0.0432(4) Uani d . 1 . . C C18 0.09168(15) 0.79137(15) 0.80623(10) 0.0376(4) Uani d . 1 . . C C19 0.11366(13) 0.81656(13) 0.72887(9) 0.0319(3) Uani d . 1 . . C C110 0.03700(14) 0.90262(14) 0.68001(9) 0.0348(4) Uani d . 1 . . C C111 0.34968(14) 0.73366(14) 0.60124(9) 0.0340(3) Uani d . 1 . . C O3 0.32676(12) 0.89822(12) 0.39975(7) 0.0528(3) Uani d . 1 . . O C31 0.43030(16) 0.97600(16) 0.39884(10) 0.0444(4) Uani d . 1 . . C C32 0.42512(18) 1.02307(18) 0.31655(10) 0.0500(5) Uani d . 1 . . C H1A 0.5300 0.5736 0.6287 0.037 Uiso calc R 1 . . H H1B 0.5788 0.5237 0.5605 0.037 Uiso calc R 1 . . H H2A 0.5928 0.3942 0.7008 0.043 Uiso calc R 1 . . H H2B 0.6258 0.3409 0.6206 0.043 Uiso calc R 1 . . H H3A 0.4252 0.2762 0.6357 0.044 Uiso calc R 1 . . H H3B 0.3815 0.4157 0.6359 0.044 Uiso calc R 1 . . H H4 0.4522 0.2989 0.5097 0.039 Uiso calc R 1 . . H H51A 0.2711 0.1450 0.5146 0.072 Uiso calc R 1 . . H H51B 0.1344 0.2028 0.5004 0.072 Uiso calc R 1 . . H H51C 0.2291 0.2242 0.5830 0.072 Uiso calc R 1 . . H H52A 0.1888 0.4469 0.5627 0.066 Uiso calc R 1 . . H H52B 0.1067 0.4324 0.4750 0.066 Uiso calc R 1 . . H H52C 0.2284 0.5167 0.4897 0.066 Uiso calc R 1 . . H H6A 0.3246 0.2484 0.3956 0.044 Uiso calc R 1 . . H H6B 0.1795 0.2784 0.3795 0.044 Uiso calc R 1 . . H H7 0.2191 0.4842 0.3547 0.042 Uiso calc R 1 . . H H71A 0.2876 0.4582 0.2340 0.064 Uiso calc R 1 . . H H71B 0.1941 0.3499 0.2443 0.064 Uiso calc R 1 . . H H71C 0.3411 0.3258 0.2614 0.064 Uiso calc R 1 . . H H11 0.2641 0.7030 0.7323 0.038 Uiso calc R 1 . . H H13 0.1788 0.8979 0.5283 0.044 Uiso calc R 1 . . H H14 0.0128 0.9877 0.5712 0.046 Uiso calc R 1 . . H H15 -0.1156 1.0140 0.6768 0.052 Uiso calc R 1 . . H H16 -0.1447 0.9732 0.8035 0.056 Uiso calc R 1 . . H H17 -0.0160 0.8329 0.8851 0.052 Uiso calc R 1 . . H H18 0.1426 0.7340 0.8393 0.045 Uiso calc R 1 . . H H3 0.3368 0.8616 0.4435 0.079 Uiso calc R 1 . . H H31A 0.5087 0.9302 0.4168 0.053 Uiso calc R 1 . . H H31B 0.4288 1.0452 0.4357 0.053 Uiso calc R 1 . . H H32A 0.3463 1.0662 0.2984 0.075 Uiso calc R 1 . . H H32B 0.4311 0.9546 0.2808 0.075 Uiso calc R 1 . . H H32C 0.4947 1.0793 0.3166 0.075 Uiso calc R 1 . . H 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 N1 0.0325(7) 0.0346(7) 0.0276(6) 0.0034(5) 0.0087(5) 0.0004(5) C2 0.0434(9) 0.0331(8) 0.0308(8) 0.0040(7) 0.0085(6) 0.0039(6) C3 0.0445(9) 0.0376(9) 0.0317(8) -0.0017(7) 0.0141(7) 0.0026(7) N4 0.0341(7) 0.0344(7) 0.0311(6) 0.0002(5) 0.0119(5) -0.0018(5) C5 0.0334(8) 0.0382(9) 0.0390(9) -0.0030(6) 0.0127(7) 0.0007(7) C51 0.0469(10) 0.0466(10) 0.0527(11) -0.0106(8) 0.0152(8) 0.0039(8) C52 0.0399(9) 0.0511(10) 0.0443(9) 0.0053(8) 0.0169(7) 0.0001(8) C6 0.0357(8) 0.0360(8) 0.0385(9) -0.0010(6) 0.0070(7) -0.0031(7) C7 0.0314(8) 0.0383(9) 0.0343(8) 0.0030(6) 0.0059(6) -0.0020(7) C71 0.0463(10) 0.0466(10) 0.0340(8) 0.0035(8) 0.0036(7) -0.0038(7) O1 0.0469(7) 0.0525(7) 0.0414(6) 0.0206(6) 0.0177(5) 0.0117(6) O2 0.0492(7) 0.0488(7) 0.0388(6) 0.0102(5) 0.0207(5) 0.0083(5) C11 0.0318(8) 0.0282(7) 0.0360(8) 0.0019(6) 0.0069(6) 0.0010(6) C12 0.0305(8) 0.0294(8) 0.0336(8) 0.0004(6) 0.0074(6) -0.0015(6) C13 0.0391(9) 0.0384(9) 0.0324(8) 0.0031(7) 0.0079(7) 0.0017(7) C14 0.0370(8) 0.0384(9) 0.0389(9) 0.0072(7) 0.0047(7) 0.0039(7) C15 0.0368(9) 0.0424(9) 0.0507(10) 0.0091(7) 0.0106(7) 0.0021(8) C16 0.0395(9) 0.0513(10) 0.0539(11) 0.0066(8) 0.0206(8) -0.0022(9) C17 0.0424(9) 0.0467(10) 0.0446(9) -0.0014(8) 0.0187(8) -0.0007(8) C18 0.0373(8) 0.0374(9) 0.0397(9) -0.0010(7) 0.0117(7) 0.0028(7) C19 0.0294(7) 0.0299(7) 0.0373(8) -0.0020(6) 0.0086(6) -0.0010(6) C110 0.0311(8) 0.0339(8) 0.0398(8) 0.0004(6) 0.0079(6) -0.0029(7) C111 0.0351(8) 0.0317(8) 0.0366(8) 0.0012(6) 0.0103(7) -0.0016(7) O3 0.0558(8) 0.0567(8) 0.0439(7) -0.0062(6) 0.0052(6) 0.0125(6) C31 0.0484(10) 0.0435(10) 0.0400(9) 0.0004(8) 0.0058(7) -0.0043(8) C32 0.0579(11) 0.0538(11) 0.0409(9) -0.0116(9) 0.0165(8) -0.0085(8) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 N1 C7 . 3_666 115.40(12) no C2 N1 H1A . . 108.4 no C7 N1 H1A 3_666 . 108.4 no C2 N1 H1B . . 108.4 no C7 N1 H1B 3_666 . 108.4 no H1A N1 H1B . . 107.5 no N1 C2 C3 . . 111.07(13) no N1 C2 H2A . . 109.4 no C3 C2 H2A . . 109.4 no N1 C2 H2B . . 109.4 no C3 C2 H2B . . 109.4 no H2A C2 H2B . . 108.0 no N4 C3 C2 . . 110.36(12) no N4 C3 H3A . . 109.6 no C2 C3 H3A . . 109.6 no N4 C3 H3B . . 109.6 no C2 C3 H3B . . 109.6 no H3A C3 H3B . . 108.1 no C3 N4 C5 . . 116.74(11) no C3 N4 H4 . . 108.1 no C5 N4 H4 . . 108.1 no N4 C5 C52 . . 108.86(13) no N4 C5 C6 . . 107.32(12) no C52 C5 C6 . . 110.56(13) no N4 C5 C51 . . 112.34(13) no C52 C5 C51 . . 109.90(13) no C6 C5 C51 . . 107.84(13) no C5 C51 H51A . . 109.5 no C5 C51 H51B . . 109.5 no H51A C51 H51B . . 109.5 no C5 C51 H51C . . 109.5 no H51A C51 H51C . . 109.5 no H51B C51 H51C . . 109.5 no C5 C52 H52A . . 109.5 no C5 C52 H52B . . 109.5 no H52A C52 H52B . . 109.5 no C5 C52 H52C . . 109.5 no H52A C52 H52C . . 109.5 no H52B C52 H52C . . 109.5 no C7 C6 C5 . . 118.01(13) no C7 C6 H6A . . 107.8 no C5 C6 H6A . . 107.8 no C7 C6 H6B . . 107.8 no C5 C6 H6B . . 107.8 no H6A C6 H6B . . 107.1 no N1 C7 C71 3_666 . 110.27(12) no N1 C7 C6 3_666 . 109.38(12) no C71 C7 C6 . . 111.17(13) no N1 C7 H7 3_666 . 108.7 no C71 C7 H7 . . 108.7 no C6 C7 H7 . . 108.7 no C7 C71 H71A . . 109.5 no C7 C71 H71B . . 109.5 no H71A C71 H71B . . 109.5 no C7 C71 H71C . . 109.5 no H71A C71 H71C . . 109.5 no H71B C71 H71C . . 109.5 no C12 C11 C19 . . 121.69(14) no C12 C11 H11 . . 119.2 no C19 C11 H11 . . 119.2 no C11 C12 C13 . . 119.26(13) no C11 C12 C111 . . 119.48(13) no C13 C12 C111 . . 121.23(13) no C14 C13 C12 . . 120.43(14) no C14 C13 H13 . . 119.8 no C12 C13 H13 . . 119.8 no C13 C14 C110 . . 121.18(15) no C13 C14 H14 . . 119.4 no C110 C14 H14 . . 119.4 no C16 C15 C110 . . 120.70(16) no C16 C15 H15 . . 119.7 no C110 C15 H15 . . 119.7 no C15 C16 C17 . . 120.71(15) no C15 C16 H16 . . 119.6 no C17 C16 H16 . . 119.6 no C18 C17 C16 . . 120.40(16) no C18 C17 H17 . . 119.8 no C16 C17 H17 . . 119.8 no C17 C18 C19 . . 120.22(15) no C17 C18 H18 . . 119.9 no C19 C18 H18 . . 119.9 no C11 C19 C110 . . 118.85(14) no C11 C19 C18 . . 121.76(14) no C110 C19 C18 . . 119.34(14) no C14 C110 C15 . . 122.81(15) no C14 C110 C19 . . 118.59(13) no C15 C110 C19 . . 118.59(14) no O2 C111 O1 . . 124.89(14) no O2 C111 C12 . . 119.51(14) no O1 C111 C12 . . 115.60(13) no C31 O3 H3 . . 109.5 no O3 C31 C32 . . 109.68(14) no O3 C31 H31A . . 109.7 no C32 C31 H31A . . 109.7 no O3 C31 H31B . . 109.7 no C32 C31 H31B . . 109.7 no H31A C31 H31B . . 108.2 no C31 C32 H32A . . 109.5 no C31 C32 H32B . . 109.5 no H32A C32 H32B . . 109.5 no C31 C32 H32C . . 109.5 no H32A C32 H32C . . 109.5 no H32B C32 H32C . . 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 . 1.487(2) y N1 C7 3_666 1.501(2) y N1 H1A . 0.92 no N1 H1B . 0.92 no C2 C3 . 1.508(2) no C2 H2A . 0.99 no C2 H2B . 0.99 no N4 C3 . 1.465(2) y C3 H3A . 0.99 no C3 H3B . 0.99 no N4 C5 . 1.495(2) y N4 H4 . 0.92 no C5 C52 . 1.536(2) no C5 C6 . 1.539(2) no C5 C51 . 1.540(2) no C51 H51A . 0.98 no C51 H51B . 0.98 no C51 H51C . 0.98 no C52 H52A . 0.98 no C52 H52B . 0.98 no C52 H52C . 0.98 no C6 C7 . 1.526(2) no C6 H6A . 0.99 no C6 H6B . 0.99 no C7 C71 . 1.524(2) no C7 H7 . 1.00 no C71 H71A . 0.98 no C71 H71B . 0.98 no C71 H71C . 0.98 no O1 C111 . 1.2602(19) no O2 C111 . 1.2538(18) no C11 C12 . 1.370(2) no C11 C19 . 1.419(2) no C11 H11 . 0.95 no C12 C13 . 1.418(2) no C12 C111 . 1.515(2) no C13 C14 . 1.373(2) no C13 H13 . 0.95 no C14 C110 . 1.417(2) no C14 H14 . 0.95 no C15 C16 . 1.364(2) no C15 C110 . 1.419(2) no C15 H15 . 0.95 no C16 C17 . 1.409(2) no C16 H16 . 0.95 no C17 C18 . 1.368(2) no C17 H17 . 0.95 no C18 C19 . 1.423(2) no C18 H18 . 0.95 no C19 C110 . 1.421(2) no O3 C31 . 1.421(2) no O3 H3 . 0.84 no C31 C32 . 1.494(2) no C31 H31A . 0.99 no C31 H31B . 0.99 no C32 H32A . 0.98 no C32 H32B . 0.98 no C32 H32C . 0.98 no 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 N1 H1B N4 3_666 0.92 2.04 2.791(2) 138 y N1 H1A O1 . 0.92 1.70 2.624(2) 178 y N4 H4 O2 3_666 0.92 2.30 3.136(2) 151 y O3 H3 O2 . 0.84 1.90 2.728(2) 171 y C7 H7 Cg2 4_575 1.00 2.94 3.785(2) 143 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_site_symmetry_1 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 C2 C3 N4 . . . 62.09(16) y C2 C3 N4 C5 . . . -174.22(13) y C3 N4 C5 C6 . . . -170.12(13) y N4 C5 C6 C7 . . . -69.22(17) y C5 C6 C7 N1 . . 3_666 56.87(17) y C6 C7 N1 C2 . 3_666 3_666 -163.05(12) y C7 N1 C2 C3 3_666 . . 172.03(12) y C3 N4 C5 C52 . . . 70.19(16) no C3 N4 C5 C51 . . . -51.76(18) no C52 C5 C6 C7 . . . 49.37(18) no C51 C5 C6 C7 . . . 169.54(14) no C5 C6 C7 C71 . . . 178.87(13) no C19 C11 C12 C13 . . . -0.9(2) no C19 C11 C12 C111 . . . 177.33(14) no C11 C12 C13 C14 . . . 0.1(2) no C111 C12 C13 C14 . . . -178.13(15) no C12 C13 C14 C110 . . . 0.6(2) no C110 C15 C16 C17 . . . -1.5(3) no C15 C16 C17 C18 . . . -0.1(3) no C16 C17 C18 C19 . . . 0.8(3) no C12 C11 C19 C110 . . . 1.1(2) no C12 C11 C19 C18 . . . -176.40(14) no C17 C18 C19 C11 . . . 177.53(15) no C17 C18 C19 C110 . . . 0.1(2) no C13 C14 C110 C15 . . . 178.26(16) no C13 C14 C110 C19 . . . -0.4(2) no C16 C15 C110 C14 . . . -176.37(16) no C16 C15 C110 C19 . . . 2.3(3) no C11 C19 C110 C14 . . . -0.4(2) no C18 C19 C110 C14 . . . 177.16(14) no C11 C19 C110 C15 . . . -179.13(14) no C18 C19 C110 C15 . . . -1.6(2) no C11 C12 C111 O2 . . . 178.54(14) no C13 C12 C111 O2 . . . -3.3(2) no C11 C12 C111 O1 . . . -2.1(2) no C13 C12 C111 O1 . . . 176.06(14) no