#------------------------------------------------------------------------------ #$Date: 2020-05-08 09:51:14 +0100 (Fri, 08 May 2020) $ #$Revision: 251911 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500109.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_3500109 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _journal_name_full 'Personal communication to COD' _journal_year 2020 _chemical_formula_moiety 'C16 H36 N, Cl, 0.07(H2 O)' _chemical_formula_sum 'C16 H36.14 Cl N O0.07' _chemical_formula_weight 279.16 _chemical_name_common 'tetrabutyl ammonium chloride hydrate' _chemical_name_systematic '1-Butanaminium, N,N,N-tributyl-, chloride, hydrate (1:0.07)' _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' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2020-04-08 _audit_creation_method ; Olex2 1.3 (compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032) ; _cell_angle_alpha 90 _cell_angle_beta 102.193(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.8700(4) _cell_length_b 14.0927(6) _cell_length_c 14.8515(7) _cell_measurement_reflns_used 9789 _cell_measurement_temperature 150 _cell_measurement_theta_max 68.341 _cell_measurement_theta_min 4.372 _cell_volume 1814.59(14) _computing_cell_refinement ; SAINT (2013) V8.32B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_collection ; SAINT (2013) V8.32B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_data_reduction ; SAINT (2013) V8.32B; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173. ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _diffrn_ambient_temperature 150 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 8.3 _diffrn_detector_type 'Bruker Platinum 135 CCD Area Detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'k-geometry diffractometer' _diffrn_measurement_device_type 'Bruker Microstar X8' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation 'Focusing mirrors' _diffrn_radiation_monochromator 'Helios Mirror Optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_unetI/netI 0.0209 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 37983 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.348 _diffrn_reflns_theta_min 4.372 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_target Cu _diffrn_source_type 'Bruker Microstar/FR591 generator' _exptl_absorpt_coefficient_mu 1.741 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.5658 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0749 before and 0.0582 after correction. The Ratio of minimum to maximum transmission is 0.7513. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.022 _exptl_crystal_description block _exptl_crystal_F_000 626.8 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_special_details ; X-ray crystallographic data for I were collected from a single crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker microstar diffractometer equipped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 110.0 degree scan in 110 frames over three different parts of the reciprocal space ; _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; _refine_diff_density_max 0.277 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.039 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 3324 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0345 _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^)+(0.0536P)^2^+0.4876P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0920 _refine_ls_wR_factor_ref 0.0931 _refine_special_details ; _shelx_SHELXL_version_number '2018/3' 1. Fixed Uiso At 1.2 times of: All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H,H) groups 2. Others Sof(O1)=Sof(H1C)=Sof(H1D)=FVAR(1) 3.a Free rotating group: O1(H1C,H1D) 3.b Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B) 3.c Idealised Me refined as rotating group: C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C) ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 3184 _reflns_number_total 3324 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c4ncl.cif _cod_data_source_block c4ncl _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 3500109 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 '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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.30003(3) 0.33736(2) 0.86547(2) 0.03183(12) Uani 1 1 d . . . . . N1 N 0.32065(10) 0.63916(6) 0.85408(6) 0.0214(2) Uani 1 1 d . . . . . C1 C 0.32573(13) 0.59645(8) 0.94902(7) 0.0241(2) Uani 1 1 d . . . . . H1A H 0.292174 0.529420 0.941088 0.029 Uiso 1 1 calc R U . . . H1B H 0.434012 0.596784 0.983840 0.029 Uiso 1 1 calc R U . . . C2 C 0.22668(15) 0.64681(9) 1.00625(8) 0.0307(3) Uani 1 1 d . . . . . H2A H 0.116410 0.639157 0.976623 0.037 Uiso 1 1 calc R U . . . H2B H 0.250877 0.715466 1.009059 0.037 Uiso 1 1 calc R U . . . C3 C 0.25573(15) 0.60636(10) 1.10352(8) 0.0348(3) Uani 1 1 d . . . . . H3A H 0.366400 0.613232 1.132545 0.042 Uiso 1 1 calc R U . . . H3B H 0.230669 0.537822 1.100433 0.042 Uiso 1 1 calc R U . . . C4 C 0.15913(19) 0.65639(10) 1.16279(10) 0.0432(3) Uani 1 1 d . . . . . H4A H 0.049425 0.645544 1.136846 0.065 Uiso 1 1 calc R U . . . H4B H 0.180626 0.724639 1.163976 0.065 Uiso 1 1 calc R U . . . H4C H 0.185266 0.631133 1.225646 0.065 Uiso 1 1 calc R U . . . C5 C 0.40041(13) 0.73530(7) 0.86174(8) 0.0245(2) Uani 1 1 d . . . . . H5A H 0.377718 0.765726 0.800272 0.029 Uiso 1 1 calc R U . . . H5B H 0.355116 0.775769 0.903674 0.029 Uiso 1 1 calc R U . . . C6 C 0.57393(14) 0.73309(8) 0.89640(8) 0.0288(3) Uani 1 1 d . . . . . H6A H 0.623540 0.706576 0.848140 0.035 Uiso 1 1 calc R U . . . H6B H 0.600118 0.691714 0.951355 0.035 Uiso 1 1 calc R U . . . C7 C 0.63426(17) 0.83310(9) 0.92115(9) 0.0382(3) Uani 1 1 d . . . . . H7A H 0.597462 0.875856 0.868177 0.046 Uiso 1 1 calc R U . . . H7B H 0.592793 0.856694 0.973849 0.046 Uiso 1 1 calc R U . . . C8 C 0.80881(19) 0.83522(12) 0.94613(11) 0.0539(4) Uani 1 1 d . . . . . H8A H 0.850101 0.812534 0.893805 0.081 Uiso 1 1 calc R U . . . H8B H 0.845405 0.794147 0.999511 0.081 Uiso 1 1 calc R U . . . H8C H 0.843879 0.900367 0.961224 0.081 Uiso 1 1 calc R U . . . C9 C 0.40228(12) 0.56932(7) 0.80272(7) 0.0232(2) Uani 1 1 d . . . . . H9A H 0.347120 0.507880 0.798564 0.028 Uiso 1 1 calc R U . . . H9B H 0.507811 0.558766 0.839441 0.028 Uiso 1 1 calc R U . . . C10 C 0.41406(14) 0.59943(8) 0.70596(8) 0.0284(3) Uani 1 1 d . . . . . H10A H 0.487695 0.652773 0.709477 0.034 Uiso 1 1 calc R U . . . H10B H 0.312038 0.621216 0.671433 0.034 Uiso 1 1 calc R U . . . C11 C 0.46906(13) 0.51551(8) 0.65576(8) 0.0270(2) Uani 1 1 d . . . . . H11A H 0.505107 0.539463 0.601280 0.032 Uiso 1 1 calc R U . . . H11B H 0.557833 0.484988 0.697273 0.032 Uiso 1 1 calc R U . . . C12 C 0.34421(15) 0.44178(10) 0.62464(9) 0.0374(3) Uani 1 1 d . . . . . H12A H 0.382807 0.392654 0.588598 0.056 Uiso 1 1 calc R U . . . H12B H 0.253452 0.472258 0.586534 0.056 Uiso 1 1 calc R U . . . H12C H 0.315753 0.412814 0.678694 0.056 Uiso 1 1 calc R U . . . C13 C 0.15581(13) 0.65564(8) 0.80280(8) 0.0249(2) Uani 1 1 d . . . . . H13A H 0.157889 0.683619 0.741930 0.030 Uiso 1 1 calc R U . . . H13B H 0.107644 0.702698 0.837447 0.030 Uiso 1 1 calc R U . . . C14 C 0.05495(14) 0.56741(9) 0.78800(9) 0.0317(3) Uani 1 1 d . . . . . H14A H 0.044460 0.541451 0.848313 0.038 Uiso 1 1 calc R U . . . H14B H 0.103849 0.518363 0.755930 0.038 Uiso 1 1 calc R U . . . C15 C -0.10436(14) 0.59188(10) 0.73053(9) 0.0366(3) Uani 1 1 d . . . . . H15A H -0.174587 0.537695 0.732595 0.044 Uiso 1 1 calc R U . . . H15B H -0.145563 0.647200 0.758640 0.044 Uiso 1 1 calc R U . . . C16 C -0.10449(17) 0.61455(11) 0.63070(9) 0.0430(3) Uani 1 1 d . . . . . H16A H -0.210965 0.622461 0.596429 0.065 Uiso 1 1 calc R U . . . H16B H -0.055662 0.562479 0.603686 0.065 Uiso 1 1 calc R U . . . H16C H -0.046917 0.673364 0.627463 0.065 Uiso 1 1 calc R U . . . O1 O 0.1230(19) 0.4123(11) 1.0148(12) 0.052(6) Uani 0.070(4) 1 d G . P . 1 H1C H 0.193039 0.404082 0.982410 0.078 Uiso 0.070(4) 1 d G U P . 1 H1D H 0.119747 0.473462 1.022319 0.078 Uiso 0.070(4) 1 d G U P . 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0439(2) 0.02259(17) 0.02710(18) -0.00038(10) 0.00329(13) -0.00363(10) N1 0.0256(5) 0.0165(4) 0.0217(5) 0.0010(3) 0.0040(4) 0.0007(3) C1 0.0292(6) 0.0209(5) 0.0221(5) 0.0043(4) 0.0050(4) 0.0021(4) C2 0.0385(7) 0.0284(6) 0.0269(6) 0.0028(5) 0.0104(5) 0.0063(5) C3 0.0412(7) 0.0375(7) 0.0279(6) 0.0050(5) 0.0121(5) 0.0055(5) C4 0.0567(9) 0.0437(8) 0.0349(7) 0.0011(6) 0.0227(7) 0.0022(6) C5 0.0335(6) 0.0151(5) 0.0248(5) -0.0004(4) 0.0058(4) -0.0021(4) C6 0.0331(6) 0.0265(6) 0.0258(6) 0.0001(4) 0.0038(5) -0.0063(5) C7 0.0520(8) 0.0350(7) 0.0309(7) -0.0089(5) 0.0163(6) -0.0194(6) C8 0.0550(9) 0.0660(11) 0.0411(8) -0.0106(7) 0.0110(7) -0.0356(8) C9 0.0273(5) 0.0176(5) 0.0248(5) -0.0007(4) 0.0059(4) 0.0015(4) C10 0.0382(6) 0.0222(6) 0.0260(6) 0.0005(4) 0.0098(5) -0.0007(5) C11 0.0277(5) 0.0278(6) 0.0262(6) -0.0022(4) 0.0071(4) -0.0008(4) C12 0.0404(7) 0.0367(7) 0.0368(7) -0.0140(5) 0.0122(5) -0.0088(6) C13 0.0249(6) 0.0235(6) 0.0252(6) 0.0029(4) 0.0028(4) 0.0023(4) C14 0.0294(6) 0.0291(6) 0.0348(6) 0.0059(5) 0.0025(5) -0.0039(5) C15 0.0271(6) 0.0407(7) 0.0400(7) 0.0021(6) 0.0025(5) -0.0041(5) C16 0.0438(7) 0.0420(8) 0.0372(7) 0.0009(6) -0.0052(6) -0.0041(6) O1 0.052(10) 0.050(10) 0.059(11) -0.006(7) 0.021(7) -0.003(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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_1 _geom_angle_site_symmetry_3 C5 N1 C1 111.09(8) . . C9 N1 C1 106.52(8) . . C9 N1 C5 110.55(8) . . C13 N1 C1 111.21(8) . . C13 N1 C5 106.55(8) . . C13 N1 C9 110.99(8) . . N1 C1 H1A 108.5 . . N1 C1 H1B 108.5 . . H1A C1 H1B 107.5 . . C2 C1 N1 115.14(9) . . C2 C1 H1A 108.5 . . C2 C1 H1B 108.5 . . C1 C2 H2A 109.5 . . C1 C2 H2B 109.5 . . C1 C2 C3 110.69(10) . . H2A C2 H2B 108.1 . . C3 C2 H2A 109.5 . . C3 C2 H2B 109.5 . . C2 C3 H3A 109.3 . . C2 C3 H3B 109.3 . . C2 C3 C4 111.80(11) . . H3A C3 H3B 107.9 . . C4 C3 H3A 109.3 . . C4 C3 H3B 109.3 . . C3 C4 H4A 109.5 . . C3 C4 H4B 109.5 . . C3 C4 H4C 109.5 . . H4A C4 H4B 109.5 . . H4A C4 H4C 109.5 . . H4B C4 H4C 109.5 . . N1 C5 H5A 108.4 . . N1 C5 H5B 108.4 . . H5A C5 H5B 107.5 . . C6 C5 N1 115.44(9) . . C6 C5 H5A 108.4 . . C6 C5 H5B 108.4 . . C5 C6 H6A 109.7 . . C5 C6 H6B 109.7 . . C5 C6 C7 110.01(10) . . H6A C6 H6B 108.2 . . C7 C6 H6A 109.7 . . C7 C6 H6B 109.7 . . C6 C7 H7A 109.3 . . C6 C7 H7B 109.3 . . H7A C7 H7B 108.0 . . C8 C7 C6 111.47(12) . . C8 C7 H7A 109.3 . . C8 C7 H7B 109.3 . . C7 C8 H8A 109.5 . . C7 C8 H8B 109.5 . . C7 C8 H8C 109.5 . . H8A C8 H8B 109.5 . . H8A C8 H8C 109.5 . . H8B C8 H8C 109.5 . . N1 C9 H9A 108.4 . . N1 C9 H9B 108.4 . . N1 C9 C10 115.36(9) . . H9A C9 H9B 107.5 . . C10 C9 H9A 108.4 . . C10 C9 H9B 108.4 . . C9 C10 H10A 109.7 . . C9 C10 H10B 109.7 . . C9 C10 C11 109.67(9) . . H10A C10 H10B 108.2 . . C11 C10 H10A 109.7 . . C11 C10 H10B 109.7 . . C10 C11 H11A 109.0 . . C10 C11 H11B 109.0 . . H11A C11 H11B 107.8 . . C12 C11 C10 112.95(10) . . C12 C11 H11A 109.0 . . C12 C11 H11B 109.0 . . C11 C12 H12A 109.5 . . C11 C12 H12B 109.5 . . C11 C12 H12C 109.5 . . H12A C12 H12B 109.5 . . H12A C12 H12C 109.5 . . H12B C12 H12C 109.5 . . N1 C13 H13A 108.5 . . N1 C13 H13B 108.5 . . N1 C13 C14 115.01(9) . . H13A C13 H13B 107.5 . . C14 C13 H13A 108.5 . . C14 C13 H13B 108.5 . . C13 C14 H14A 109.7 . . C13 C14 H14B 109.7 . . C13 C14 C15 110.05(10) . . H14A C14 H14B 108.2 . . C15 C14 H14A 109.7 . . C15 C14 H14B 109.7 . . C14 C15 H15A 108.8 . . C14 C15 H15B 108.8 . . H15A C15 H15B 107.7 . . C16 C15 C14 113.79(11) . . C16 C15 H15A 108.8 . . C16 C15 H15B 108.8 . . C15 C16 H16A 109.5 . . C15 C16 H16B 109.5 . . C15 C16 H16C 109.5 . . H16A C16 H16B 109.5 . . H16A C16 H16C 109.5 . . H16B C16 H16C 109.5 . . H1C O1 H1D 104.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C1 1.5249(13) . N1 C5 1.5217(13) . N1 C9 1.5192(13) . N1 C13 1.5170(14) . C1 H1A 0.9900 . C1 H1B 0.9900 . C1 C2 1.5209(16) . C2 H2A 0.9900 . C2 H2B 0.9900 . C2 C3 1.5236(16) . C3 H3A 0.9900 . C3 H3B 0.9900 . C3 C4 1.5247(18) . C4 H4A 0.9800 . C4 H4B 0.9800 . C4 H4C 0.9800 . C5 H5A 0.9900 . C5 H5B 0.9900 . C5 C6 1.5167(16) . C6 H6A 0.9900 . C6 H6B 0.9900 . C6 C7 1.5246(16) . C7 H7A 0.9900 . C7 H7B 0.9900 . C7 C8 1.514(2) . C8 H8A 0.9800 . C8 H8B 0.9800 . C8 H8C 0.9800 . C9 H9A 0.9900 . C9 H9B 0.9900 . C9 C10 1.5231(15) . C10 H10A 0.9900 . C10 H10B 0.9900 . C10 C11 1.5317(16) . C11 H11A 0.9900 . C11 H11B 0.9900 . C11 C12 1.5177(16) . C12 H12A 0.9800 . C12 H12B 0.9800 . C12 H12C 0.9800 . C13 H13A 0.9900 . C13 H13B 0.9900 . C13 C14 1.5203(16) . C14 H14A 0.9900 . C14 H14B 0.9900 . C14 C15 1.5280(17) . C15 H15A 0.9900 . C15 H15B 0.9900 . C15 C16 1.5164(19) . C16 H16A 0.9800 . C16 H16B 0.9800 . C16 H16C 0.9800 . O1 H1C 0.8701 . O1 H1D 0.8703 . 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 _geom_hbond_publ_flag O1 H1C Cl1 0.87 2.34 3.158(16) 155.6 . yes 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 C1 C2 C3 -172.89(10) . . . . N1 C5 C6 C7 -167.41(9) . . . . N1 C9 C10 C11 -168.89(9) . . . . N1 C13 C14 C15 -176.37(10) . . . . C1 N1 C5 C6 68.69(11) . . . . C1 N1 C9 C10 -178.56(9) . . . . C1 N1 C13 C14 -58.58(12) . . . . C1 C2 C3 C4 179.35(11) . . . . C5 N1 C1 C2 69.50(12) . . . . C5 N1 C9 C10 -57.77(12) . . . . C5 N1 C13 C14 -179.77(9) . . . . C5 C6 C7 C8 -173.79(11) . . . . C9 N1 C1 C2 -170.04(9) . . . . C9 N1 C5 C6 -49.35(12) . . . . C9 N1 C13 C14 59.82(12) . . . . C9 C10 C11 C12 74.91(13) . . . . C13 N1 C1 C2 -48.99(12) . . . . C13 N1 C5 C6 -170.04(9) . . . . C13 N1 C9 C10 60.24(12) . . . . C13 C14 C15 C16 70.26(14) . . . . _cod_database_fobs_code 3500109