Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_General _journal_coden_Cambridge 182 #------------------------------------------------------------------------------ # PROCESSING SUMMARY (IUCr Office Use Only) #------------------------------------------------------------------------------ # SUBMISSION DETAILS _publ_contact_author_name 'Dr Masakazu Ohkita ' _publ_contact_author_address ; Dr Masakazu Ohkita Division of Chemistry Hokkaido University Graduate School of Science Sapporo 060-810 JAPAN ; _publ_contact_author_email 'ohkita@science.hokudai.ac.jp ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'Chemical Communications ' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #------------------------------------------------------------------------------ # TITLE AND AUTHOR LIST _publ_section_title ; Crystal engineering using very short and linear C(sp)-H...N hydrogen bonds: formation of head-to-tail straight tapes and their assembly into nonlinear optical polar crystals ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name 'Masakazu Ohkita' 'Keitaro Nakatani' 'Takanori Suzuki' 'Takashi Tsuji' _publ_section_synopsis ; ENTER SYNOPSIS ; #------------------------------------------------------------------------------ # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1999). teXsan. Single Crystal Structure Analysis Software. Version 1.10. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #------------------------------------------------------------------------------ data_4-ethynylpyridine_-80_degr _database_code_CSD 153071 _audit_creation_date 'Fri Feb 23 19:48:27 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C7 H5 N ' _chemical_formula_moiety 'C7 H5 N ' _chemical_formula_weight 103.12 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 9.800(5) _cell_length_b 8.684(5) _cell_length_c 7.334(4) _cell_angle_alpha 90 _cell_angle_beta 116.90(4) _cell_angle_gamma 90 _cell_volume 556.6(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 193.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'rod' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_reflns_number 1480 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_theta_max 27.09 _diffrn_measured_fraction_theta_max 0.9337 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.9337 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 577 _reflns_number_gt 456 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.1138 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 456 _refine_ls_number_parameters 39 _refine_ls_goodness_of_fit_ref 3.362 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]' _refine_ls_shift/su_max 0.0053 _refine_diff_density_max 0.42 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.5000 0.8112(2) -0.2500 0.0663(5) Uani 1.00 d S . . C1 C 0.6269(2) 0.8910(2) -0.2025(3) 0.0631(4) Uani 1.00 d . . . C2 C 0.6335(2) 1.0491(2) -0.2001(3) 0.0523(4) Uani 1.00 d . . . C3 C 0.5000 1.1323(2) -0.2500 0.0449(5) Uani 1.00 d S . . C4 C 0.5000 1.2967(2) -0.2500 0.0488(5) Uani 1.00 d S . . C5 C 0.5000 1.4335(2) -0.2500 0.0604(6) Uani 1.00 d S . . H1 H 0.7193 0.8361 -0.1680 0.0698 Uiso 1.00 calc . . . H2 H 0.7290 1.0995 -0.1641 0.0578 Uiso 1.00 calc . . . H3 H 0.5000 1.5434 -0.2500 0.0667 Uiso 1.00 calc S . . 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 0.111(1) 0.0321(9) 0.0777(10) 0.0000 0.0616(8) 0.0000 C1 0.0854(9) 0.0383(7) 0.0786(9) 0.0147(7) 0.0484(7) 0.0081(7) C2 0.0584(8) 0.0381(7) 0.0642(9) 0.0034(6) 0.0311(6) 0.0033(6) C3 0.0555(9) 0.0310(9) 0.0480(9) 0.0000 0.0233(7) 0.0000 C4 0.0491(9) 0.0348(9) 0.059(1) 0.0000 0.0217(8) 0.0000 C5 0.060(1) 0.0311(10) 0.087(2) 0.0000 0.031(1) 0.0000 #------------------------------------------------------------------------------ _computing_data_collection 'S' _computing_cell_refinement 'S' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution MITHRIL90 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.325(2) . . yes N1 C1 1.325(2) . 2_654 yes C1 C2 1.374(3) . . yes C2 C3 1.391(2) . . yes C3 C4 1.428(3) . . yes C4 C5 1.188(3) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C1 116.9(2) . 1_555 2_654 yes N1 C1 C2 124.0(2) . 1_555 1_555 yes C1 C2 C3 118.8(2) . 1_555 1_555 yes C2 C3 C2 117.4(2) . 1_555 2_654 yes C2 C3 C4 121.28(10) . 1_555 1_555 yes C2 C3 C4 121.28(10) . 2_654 1_555 yes C3 C4 C5 180.0 . 1_555 1_555 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 _geom_torsion_publ_flag N1 C1 C2 C3 0.1(3) 1_555 1_555 1_555 1_555 yes N1 C1 C2 C3 0.1(3) 1_555 2_654 2_654 1_555 yes C1 N1 C1 C2 0.0(1) 1_555 1_555 2_654 2_654 yes C1 C2 C3 C2 0.0(1) 1_555 1_555 1_555 2_654 yes C1 C2 C3 C4 180.0(1) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N1 C5 3.279(3) . 1_545 ? #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_4-(4-ethynylphenyl)pyridin _database_code_CSD 164007 _audit_creation_date 'Thu Mar 1 09:44:55 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C15 H9 N ' _chemical_formula_moiety 'C15 H9 N ' _chemical_formula_weight 203.24 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'F d d 2 ' _symmetry_Int_Tables_number 43 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,z 1/4-x,1/4+y,1/4+z 1/4+x,1/4-y,1/4+z x,1/2+y,1/2+z -x,1/2-y,1/2+z 1/4-x,3/4+y,3/4+z 1/4+x,3/4-y,3/4+z 1/2+x,y,1/2+z 1/2-x,-y,1/2+z 3/4-x,1/4+y,3/4+z 3/4+x,1/4-y,3/4+z 1/2+x,1/2+y,z 1/2-x,1/2-y,z 3/4-x,3/4+y,1/4+z 3/4+x,3/4-y,1/4+z _cell_length_a 17.491(1) _cell_length_b 7.748(1) _cell_length_c 15.5880(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2112.5(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 123.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.150 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_reflns_number 2901 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.9502 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.9502 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 516 _reflns_number_gt 457 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.0715 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 457 _refine_ls_number_parameters 76 _refine_ls_goodness_of_fit_ref 2.319 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]' _refine_ls_shift/su_max 0.0063 _refine_diff_density_max 0.28 _refine_diff_density_min -0.23 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.0000 0.5000 0.0000 0.0327(9) Uani 1.00 d S . . C1 C 0.0639(2) 0.5363(4) 0.0446(2) 0.0332(7) Uani 1.00 d . . . C2 C 0.0665(1) 0.5360(4) 0.1340(2) 0.0274(7) Uani 1.00 d . . . C3 C 0.0000 0.5000 0.1795(3) 0.0266(10) Uani 1.00 d S . . C4 C 0.0000 0.5000 0.2726(3) 0.028(1) Uani 1.00 d S . . C5 C 0.0000 0.5000 0.3494(3) 0.026(1) Uani 1.00 d S . . C6 C 0.0000 0.5000 0.4413(2) 0.0222(9) Uani 1.00 d S . . C7 C 0.0686(1) 0.4857(4) 0.4874(2) 0.0269(7) Uani 1.00 d . . . C8 C 0.0680(1) 0.4857(4) 0.5758(2) 0.0232(6) Uani 1.00 d . . . C9 C 0.0000 0.5000 0.6217(2) 0.0233(9) Uani 1.00 d S . . C10 C 0.0000 0.5000 0.7114(3) 0.0263(9) Uani 1.00 d S . . C11 C 0.0000 0.5000 0.7900(3) 0.039(1) Uani 1.00 d S . . H1 H 0.1095 0.5625 0.0136 0.0390 Uiso 1.00 calc . . . H2 H 0.1131 0.5607 0.1637 0.0324 Uiso 1.00 calc . . . H3 H 0.1160 0.4781 0.4576 0.0309 Uiso 1.00 calc . . . H4 H 0.1148 0.4734 0.6068 0.0281 Uiso 1.00 calc . . . H5 H 0.0000 0.5000 0.8512 0.0452 Uiso 1.00 calc S . . 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 0.046(2) 0.037(2) 0.015(1) -0.006(2) 0.0000 0.0000 C1 0.037(1) 0.034(1) 0.029(1) -0.006(1) 0.006(1) -0.001(1) C2 0.033(1) 0.028(1) 0.021(1) -0.002(1) 0.001(1) -0.006(1) C3 0.033(2) 0.017(2) 0.029(2) 0.003(2) 0.0000 0.0000 C4 0.037(2) 0.027(2) 0.021(2) 0.002(2) 0.0000 0.0000 C5 0.029(2) 0.032(2) 0.017(2) -0.001(1) 0.0000 0.0000 C6 0.031(2) 0.027(2) 0.008(1) 0.000(1) 0.0000 0.0000 C7 0.027(1) 0.031(1) 0.023(2) 0.001(1) 0.004(1) -0.002(1) C8 0.028(1) 0.031(1) 0.011(1) 0.001(1) -0.0021(10) 0.000(1) C9 0.030(2) 0.018(2) 0.022(2) 0.000(1) 0.0000 0.0000 C10 0.027(2) 0.036(2) 0.016(2) -0.001(1) 0.0000 0.0000 C11 0.027(2) 0.051(2) 0.038(3) -0.001(2) 0.0000 0.0000 #------------------------------------------------------------------------------ _computing_data_collection 'S' _computing_cell_refinement 'S' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.346(3) . . yes N1 C1 1.346(3) . 2_565 yes C1 C2 1.394(4) . . yes C2 C3 1.390(3) . . yes C3 C4 1.450(5) . . yes C4 C5 1.197(5) . . yes C5 C6 1.433(5) . . yes C6 C7 1.403(3) . . yes C6 C7 1.403(3) . 2_565 yes C7 C8 1.378(4) . . yes C8 C9 1.392(3) . . yes C9 C10 1.398(5) . . yes C10 C11 1.226(7) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C1 117.8(3) . 1_555 2_565 yes N1 C1 C2 122.9(3) . 1_555 1_555 yes C1 C2 C3 118.9(3) . 1_555 1_555 yes C2 C3 C2 118.6(3) . 1_555 2_565 yes C2 C3 C4 120.7(2) . 1_555 1_555 yes C2 C3 C4 120.7(2) . 2_565 1_555 yes C3 C4 C5 180.0000(1) . 1_555 1_555 yes C4 C5 C6 180.0000(1) . 1_555 1_555 yes C5 C6 C7 120.8(2) . 1_555 1_555 yes C5 C6 C7 120.8(2) . 1_555 2_565 yes C7 C6 C7 118.4(3) . 1_555 2_565 yes C6 C7 C8 120.3(2) . 1_555 1_555 yes C7 C8 C9 121.4(2) . 1_555 1_555 yes C8 C9 C8 118.1(3) . 1_555 2_565 yes C8 C9 C10 120.9(2) . 1_555 1_555 yes C8 C9 C10 120.9(2) . 2_565 1_555 yes C9 C10 C11 180.0000(1) . 1_555 1_555 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 _geom_torsion_publ_flag N1 C1 C2 C3 -1.2(4) 1_555 1_555 1_555 1_555 yes N1 C1 C2 H2 179.0(2) 1_555 1_555 1_555 1_555 no N1 C1 C2 C3 -1.2(4) 1_555 2_565 2_565 1_555 yes N1 C1 C2 H2 179.0(2) 1_555 2_565 2_565 2_565 no C1 N1 C1 C2 0.6(2) 1_555 1_555 2_565 2_565 yes C1 N1 C1 H1 -179.9(4) 1_555 1_555 2_565 2_565 no C1 C2 C3 C2 0.6(2) 1_555 1_555 1_555 2_565 yes C1 C2 C3 C4 -179.4(2) 1_555 1_555 1_555 1_555 yes C2 C3 C2 H2 -179.7(3) 1_555 1_555 2_565 2_565 no C3 C2 C1 H1 179.3(2) 1_555 1_555 1_555 1_555 no C3 C2 C1 H1 179.3(2) 1_555 2_565 2_565 2_565 no C4 C3 C2 H2 0.3(3) 1_555 1_555 1_555 1_555 no C4 C3 C2 H2 0.3(3) 1_555 1_555 2_565 2_565 no C5 C6 C7 C8 -180.0(2) 1_555 1_555 1_555 1_555 yes C5 C6 C7 H3 1.3(3) 1_555 1_555 1_555 1_555 no C5 C6 C7 C8 -180.0(2) 1_555 1_555 2_565 2_565 yes C5 C6 C7 H3 1.3(3) 1_555 1_555 2_565 2_565 no C6 C7 C8 C9 -0.1(4) 1_555 1_555 1_555 1_555 yes C6 C7 C8 H4 178.7(2) 1_555 1_555 1_555 1_555 no C6 C7 C8 C9 -0.1(4) 1_555 2_565 2_565 1_555 yes C6 C7 C8 H4 178.7(2) 1_555 2_565 2_565 2_565 no C7 C6 C7 C8 0.0(2) 1_555 1_555 2_565 2_565 yes C7 C6 C7 H3 -178.7(3) 1_555 1_555 2_565 2_565 no C7 C8 C9 C8 0.0(2) 1_555 1_555 1_555 2_565 yes C7 C8 C9 C10 -180.0(2) 1_555 1_555 1_555 1_555 yes C8 C9 C8 H4 -178.7(3) 1_555 1_555 2_565 2_565 no C9 C8 C7 H3 178.7(2) 1_555 1_555 1_555 1_555 no C9 C8 C7 H3 178.7(2) 1_555 2_565 2_565 2_565 no C10 C9 C8 H4 1.3(3) 1_555 1_555 1_555 1_555 no C10 C9 C8 H4 1.3(3) 1_555 1_555 2_565 2_565 no H1 C1 C2 H2 -0.5(5) 1_555 1_555 1_555 1_555 no H3 C7 C8 H4 -2.6(5) 1_555 1_555 1_555 1_555 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag N1 C11 3.273(5) . 1_554 ? C1 C8 3.516(4) . 5_554 ? C1 C7 3.595(4) . 5_554 ? C2 C7 3.472(4) . 7_544 ? #------------------------------------------------------------------------------