Electronic Supplementary MAterial for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_section_title ; Syntheses, crystal structures, and polymorphism of quaternary pyrrolidinium chlorides ; _publ_contact_author_name 'Gerhard Laus' _publ_contact_author_email Gerhard.Laus@uibk.ac.at loop_ _publ_author_name 'Gerhard Laus' 'Gino Bentivoglio' 'Volker Kahlenberg' 'Ulrich Griesser' 'Herwig Schottenberger' ; G.Nauer ; # Attachment 'LAUS_crystal_data.cif' data_CCDC617232 _database_code_depnum_ccdc_archive 'CCDC 617232' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H18 N, Cl' _chemical_formula_sum 'C8 H18 Cl N' _chemical_formula_weight 163.68 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' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a b' _symmetry_space_group_name_Hall '-P 2bc 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y-1/2, z-1/2' 'x-1/2, -y, z' _cell_length_a 10.0354(11) _cell_length_b 13.254(2) _cell_length_c 14.6231(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1945.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9408 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 27.33 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.373 _exptl_crystal_size_min 0.360 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13824 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.91 _reflns_number_total 2088 _reflns_number_gt 1666 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.7636P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2088 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.44781(4) 0.32505(3) 0.35988(3) 0.03624(13) Uani 1 1 d . . . N1 N 0.56509(13) 0.13139(10) 0.17048(9) 0.0279(3) Uani 1 1 d . . . C1 C 0.58020(19) 0.24077(13) 0.14224(13) 0.0368(4) Uani 1 1 d . . . H1A H 0.6617 0.2501 0.1051 0.044 Uiso 1 1 calc R . . H1B H 0.5858 0.2849 0.1967 0.044 Uiso 1 1 calc R . . C2 C 0.61939(18) 0.06431(13) 0.09649(11) 0.0315(4) Uani 1 1 d . . . H2A H 0.7167 0.0700 0.0949 0.047 Uiso 1 1 calc R . . H2B H 0.5825 0.0850 0.0373 0.047 Uiso 1 1 calc R . . H2C H 0.5944 -0.0058 0.1090 0.047 Uiso 1 1 calc R . . C3 C 0.4568(2) 0.26528(15) 0.08643(15) 0.0484(5) Uani 1 1 d . . . H3A H 0.4803 0.2736 0.0211 0.058 Uiso 1 1 calc R . . H3B H 0.4154 0.3286 0.1085 0.058 Uiso 1 1 calc R . . C4 C 0.63578(17) 0.11388(12) 0.25985(11) 0.0305(4) Uani 1 1 d . . . H4A H 0.6030 0.1638 0.3050 0.037 Uiso 1 1 calc R . . H4B H 0.7322 0.1263 0.2508 0.037 Uiso 1 1 calc R . . C5 C 0.3609(2) 0.17657(16) 0.09866(14) 0.0469(5) Uani 1 1 d . . . H5A H 0.2696 0.2008 0.1118 0.056 Uiso 1 1 calc R . . H5B H 0.3587 0.1340 0.0430 0.056 Uiso 1 1 calc R . . C6 C 0.6873(3) 0.00214(18) 0.39098(14) 0.0564(6) Uani 1 1 d . . . H6A H 0.7835 0.0106 0.3824 0.085 Uiso 1 1 calc R . . H6B H 0.6695 -0.0640 0.4184 0.085 Uiso 1 1 calc R . . H6C H 0.6538 0.0553 0.4314 0.085 Uiso 1 1 calc R . . C7 C 0.6179(2) 0.00905(14) 0.29939(12) 0.0386(4) Uani 1 1 d . . . H7A H 0.5218 -0.0056 0.3070 0.046 Uiso 1 1 calc R . . H7B H 0.6558 -0.0416 0.2570 0.046 Uiso 1 1 calc R . . C8 C 0.41640(17) 0.11811(15) 0.17924(13) 0.0366(4) Uani 1 1 d . . . H8A H 0.3836 0.1461 0.2378 0.044 Uiso 1 1 calc R . . H8B H 0.3915 0.0460 0.1756 0.044 Uiso 1 1 calc R . . 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 0.0344(2) 0.0383(2) 0.0360(2) -0.00566(19) 0.0023(2) 0.00254(18) N1 0.0275(7) 0.0289(7) 0.0273(7) -0.0021(5) -0.0023(6) 0.0006(6) C1 0.0434(10) 0.0284(8) 0.0386(9) 0.0009(7) -0.0016(9) 0.0019(7) C2 0.0348(9) 0.0334(9) 0.0263(8) -0.0033(7) 0.0002(7) 0.0024(7) C3 0.0582(13) 0.0444(11) 0.0426(11) 0.0006(9) -0.0069(10) 0.0178(10) C4 0.0326(8) 0.0321(8) 0.0267(8) -0.0039(7) -0.0040(7) -0.0013(7) C5 0.0369(10) 0.0605(13) 0.0432(11) -0.0111(10) -0.0090(9) 0.0147(9) C6 0.0816(16) 0.0478(11) 0.0397(10) 0.0067(10) -0.0203(12) -0.0100(11) C7 0.0464(11) 0.0378(10) 0.0316(9) 0.0018(8) -0.0051(8) -0.0070(8) C8 0.0257(8) 0.0464(10) 0.0379(9) -0.0065(8) -0.0005(7) -0.0011(7) _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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.503(2) . ? N1 C4 1.505(2) . ? N1 C8 1.508(2) . ? N1 C1 1.515(2) . ? C1 C3 1.518(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C5 1.530(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C7 1.516(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C8 1.516(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.512(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 _geom_angle_publ_flag C2 N1 C4 111.29(13) . . ? C2 N1 C8 110.54(13) . . ? C4 N1 C8 112.00(13) . . ? C2 N1 C1 109.49(13) . . ? C4 N1 C1 109.70(13) . . ? C8 N1 C1 103.53(13) . . ? N1 C1 C3 105.65(15) . . ? N1 C1 H1A 110.6 . . ? C3 C1 H1A 110.6 . . ? N1 C1 H1B 110.6 . . ? C3 C1 H1B 110.6 . . ? H1A C1 H1B 108.7 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 C5 106.61(15) . . ? C1 C3 H3A 110.4 . . ? C5 C3 H3A 110.4 . . ? C1 C3 H3B 110.4 . . ? C5 C3 H3B 110.4 . . ? H3A C3 H3B 108.6 . . ? N1 C4 C7 114.65(13) . . ? N1 C4 H4A 108.6 . . ? C7 C4 H4A 108.6 . . ? N1 C4 H4B 108.6 . . ? C7 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C8 C5 C3 104.61(16) . . ? C8 C5 H5A 110.8 . . ? C3 C5 H5A 110.8 . . ? C8 C5 H5B 110.8 . . ? C3 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C7 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C7 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C6 C7 C4 109.82(15) . . ? C6 C7 H7A 109.7 . . ? C4 C7 H7A 109.7 . . ? C6 C7 H7B 109.7 . . ? C4 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? N1 C8 C5 103.76(15) . . ? N1 C8 H8A 111.0 . . ? C5 C8 H8A 111.0 . . ? N1 C8 H8B 111.0 . . ? C5 C8 H8B 111.0 . . ? H8A C8 H8B 109.0 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.91 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.176 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.038 #===END data_CCDC617233 _database_code_depnum_ccdc_archive 'CCDC 617233' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H16 N, Cl' _chemical_formula_sum 'C8 H16 Cl N' _chemical_formula_weight 161.67 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' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc 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' _cell_length_a 6.4857(10) _cell_length_b 12.005(3) _cell_length_c 12.526(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.746(13) _cell_angle_gamma 90.00 _cell_volume 951.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4775 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.23 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.133 _exptl_crystal_size_min 0.100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.129 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7080 _diffrn_reflns_av_R_equivalents 0.0621 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.55 _reflns_number_total 1900 _reflns_number_gt 1402 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA' _computing_data_reduction 'STOE X-RED' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.2336P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1900 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.0970 _refine_ls_wR_factor_gt 0.0878 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.62337(9) 0.03594(4) 0.77889(4) 0.03035(19) Uani 1 1 d . . . N1 N 0.8406(3) 0.36494(13) 0.64581(14) 0.0243(4) Uani 1 1 d . . . C2 C 0.8109(4) 0.47480(18) 0.58797(19) 0.0317(5) Uani 1 1 d . . . H2A H 0.7706 0.4624 0.5088 0.048 Uiso 1 1 calc R . . H2B H 0.9433 0.5171 0.6057 0.048 Uiso 1 1 calc R . . H2C H 0.6993 0.5169 0.6115 0.048 Uiso 1 1 calc R . . C3 C 0.9104(4) 0.3803(2) 0.76823(17) 0.0318(5) Uani 1 1 d . . . H3A H 0.7884 0.3982 0.8008 0.038 Uiso 1 1 calc R . . H3B H 1.0161 0.4408 0.7861 0.038 Uiso 1 1 calc R . . C4 C 0.6353(4) 0.29921(17) 0.62100(17) 0.0275(5) Uani 1 1 d . . . H4A H 0.6485 0.2354 0.6721 0.033 Uiso 1 1 calc R . . H4B H 0.5199 0.3475 0.6344 0.033 Uiso 1 1 calc R . . C5 C 1.0071(4) 0.2685(2) 0.80979(19) 0.0398(6) Uani 1 1 d . . . H5A H 0.9023 0.2215 0.8355 0.048 Uiso 1 1 calc R . . H5B H 1.1312 0.2792 0.8710 0.048 Uiso 1 1 calc R . . C6 C 0.5427(5) 0.1501(2) 0.4852(2) 0.0424(6) Uani 1 1 d . . . H6A H 0.5556 0.0985 0.5437 0.051 Uiso 1 1 calc R . . H6B H 0.5055 0.1248 0.4116 0.051 Uiso 1 1 calc R . . C7 C 1.0210(4) 0.29983(18) 0.62005(19) 0.0306(5) Uani 1 1 d . . . H7A H 1.1438 0.3488 0.6200 0.037 Uiso 1 1 calc R . . H7B H 0.9787 0.2631 0.5478 0.037 Uiso 1 1 calc R . . C8 C 0.5763(4) 0.25624(19) 0.50592(19) 0.0323(5) Uani 1 1 d . . . H8 H 0.5629 0.3072 0.4467 0.039 Uiso 1 1 calc R . . C10 C 1.0734(4) 0.2140(2) 0.7113(2) 0.0411(6) Uani 1 1 d . . . H10A H 1.2265 0.1969 0.7288 0.049 Uiso 1 1 calc R . . H10B H 0.9937 0.1442 0.6900 0.049 Uiso 1 1 calc R . . 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 0.0306(3) 0.0277(3) 0.0327(3) 0.0020(2) 0.0084(2) -0.0013(2) N1 0.0233(11) 0.0233(8) 0.0259(8) -0.0005(6) 0.0066(7) -0.0016(7) C2 0.0338(14) 0.0247(10) 0.0374(12) 0.0035(9) 0.0113(10) -0.0021(9) C3 0.0344(15) 0.0361(12) 0.0250(10) -0.0026(9) 0.0077(9) -0.0085(9) C4 0.0228(13) 0.0264(10) 0.0327(11) -0.0004(8) 0.0061(9) -0.0031(8) C5 0.0370(17) 0.0452(14) 0.0326(12) 0.0098(10) -0.0020(10) -0.0079(11) C6 0.0482(18) 0.0387(12) 0.0362(13) 0.0045(10) 0.0042(11) 0.0055(11) C7 0.0253(14) 0.0304(11) 0.0373(12) -0.0003(9) 0.0104(9) 0.0005(9) C8 0.0298(15) 0.0314(11) 0.0327(11) 0.0021(9) 0.0029(9) -0.0022(9) C10 0.0311(16) 0.0340(12) 0.0564(15) 0.0108(11) 0.0082(12) 0.0043(10) _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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.497(3) . ? N1 C7 1.500(3) . ? N1 C3 1.511(3) . ? N1 C4 1.520(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C5 1.524(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C8 1.499(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.539(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C8 1.309(3) . ? C6 H6A 0.9500 . ? C6 H6B 0.9500 . ? C7 C10 1.520(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8 0.9500 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? 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 _geom_angle_publ_flag C2 N1 C7 112.23(16) . . ? C2 N1 C3 111.19(16) . . ? C7 N1 C3 102.05(18) . . ? C2 N1 C4 110.18(17) . . ? C7 N1 C4 112.04(16) . . ? C3 N1 C4 108.87(16) . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C5 104.34(18) . . ? N1 C3 H3A 110.9 . . ? C5 C3 H3A 110.9 . . ? N1 C3 H3B 110.9 . . ? C5 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? C8 C4 N1 113.68(18) . . ? C8 C4 H4A 108.8 . . ? N1 C4 H4A 108.8 . . ? C8 C4 H4B 108.8 . . ? N1 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C3 C5 C10 105.49(18) . . ? C3 C5 H5A 110.6 . . ? C10 C5 H5A 110.6 . . ? C3 C5 H5B 110.6 . . ? C10 C5 H5B 110.6 . . ? H5A C5 H5B 108.8 . . ? C8 C6 H6A 120.0 . . ? C8 C6 H6B 120.0 . . ? H6A C6 H6B 120.0 . . ? N1 C7 C10 104.29(17) . . ? N1 C7 H7A 110.9 . . ? C10 C7 H7A 110.9 . . ? N1 C7 H7B 110.9 . . ? C10 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? C6 C8 C4 121.5(2) . . ? C6 C8 H8 119.3 . . ? C4 C8 H8 119.3 . . ? C7 C10 C5 105.02(19) . . ? C7 C10 H10A 110.7 . . ? C5 C10 H10A 110.7 . . ? C7 C10 H10B 110.7 . . ? C5 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 26.55 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.204 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.050 #===END data_CCDC644230 _database_code_depnum_ccdc_archive 'CCDC 644230' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H14 N, Cl' _chemical_formula_sum 'C8 H14 Cl N' _chemical_formula_weight 159.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4849(14) _cell_length_b 8.1271(16) _cell_length_c 13.501(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.408(13) _cell_angle_gamma 90.00 _cell_volume 915.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1918 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 24.61 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.349 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5415 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 24.61 _reflns_number_total 1457 _reflns_number_gt 1333 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.2996P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1457 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0713 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.44073(4) 0.69729(4) 0.15955(3) 0.02870(14) Uani 1 1 d . . . N1 N 0.48691(14) 0.22530(14) 0.26488(9) 0.0238(3) Uani 1 1 d . . . C5 C 0.35914(17) 0.24850(19) 0.17212(12) 0.0289(3) Uani 1 1 d . . . H5A H 0.3477 0.3662 0.1533 0.035 Uiso 1 1 calc R . . H5B H 0.2544 0.2067 0.1838 0.035 Uiso 1 1 calc R . . C4 C 0.4184(2) 0.1488(2) 0.08992(12) 0.0351(4) Uani 1 1 d . . . H4A H 0.3976 0.2086 0.0250 0.042 Uiso 1 1 calc R . . H4B H 0.3640 0.0406 0.0809 0.042 Uiso 1 1 calc R . . C3 C 0.5998(2) 0.1267(2) 0.12694(13) 0.0354(4) Uani 1 1 d . . . H3A H 0.6260 0.0097 0.1422 0.043 Uiso 1 1 calc R . . H3B H 0.6608 0.1650 0.0754 0.043 Uiso 1 1 calc R . . C2 C 0.63888(17) 0.23081(19) 0.22147(12) 0.0305(4) Uani 1 1 d . . . H2A H 0.7302 0.1838 0.2692 0.037 Uiso 1 1 calc R . . H2B H 0.6653 0.3451 0.2050 0.037 Uiso 1 1 calc R . . C1 C 0.4818(2) 0.35774(19) 0.34087(12) 0.0331(4) Uani 1 1 d . . . H1A H 0.4924 0.4653 0.3099 0.050 Uiso 1 1 calc R . . H1B H 0.5700 0.3422 0.3978 0.050 Uiso 1 1 calc R . . H1C H 0.3794 0.3527 0.3647 0.050 Uiso 1 1 calc R . . C6 C 0.46329(16) 0.05928(17) 0.31069(11) 0.0255(3) Uani 1 1 d . . . H6A H 0.3627 0.0608 0.3382 0.031 Uiso 1 1 calc R . . H6B H 0.4525 -0.0259 0.2575 0.031 Uiso 1 1 calc R . . C7 C 0.59655(18) 0.01611(18) 0.39104(13) 0.0288(3) Uani 1 1 d . . . C8 C 0.7052(2) -0.0230(2) 0.45427(13) 0.0360(4) Uani 1 1 d . . . H8 H 0.7926 -0.0544 0.5051 0.043 Uiso 1 1 calc R . . 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 0.0273(2) 0.0246(2) 0.0338(2) -0.00234(14) 0.00457(15) -0.00358(13) N1 0.0239(6) 0.0202(6) 0.0275(7) 0.0005(5) 0.0054(5) -0.0003(5) C5 0.0274(8) 0.0260(7) 0.0313(9) 0.0031(6) -0.0001(6) 0.0018(6) C4 0.0459(9) 0.0301(8) 0.0285(9) 0.0007(6) 0.0048(7) 0.0007(7) C3 0.0429(9) 0.0285(8) 0.0394(10) 0.0021(7) 0.0195(7) 0.0004(7) C2 0.0260(8) 0.0287(8) 0.0395(10) 0.0038(6) 0.0126(7) -0.0036(6) C1 0.0409(9) 0.0250(8) 0.0335(10) -0.0054(6) 0.0072(7) 0.0003(7) C6 0.0264(7) 0.0215(7) 0.0297(9) 0.0027(6) 0.0079(6) -0.0016(6) C7 0.0339(8) 0.0246(8) 0.0304(9) 0.0009(6) 0.0124(7) 0.0033(6) C8 0.0414(9) 0.0361(9) 0.0305(10) 0.0004(7) 0.0068(7) 0.0103(7) _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. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.4930(19) . ? N1 C2 1.5104(19) . ? N1 C6 1.5127(18) . ? N1 C5 1.5128(19) . ? C5 C4 1.531(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C4 C3 1.540(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C3 C2 1.517(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C6 C7 1.461(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.181(2) . ? C8 H8 0.9500 . ? 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 _geom_angle_publ_flag C1 N1 C2 112.23(11) . . ? C1 N1 C6 109.85(12) . . ? C2 N1 C6 111.75(11) . . ? C1 N1 C5 111.93(11) . . ? C2 N1 C5 102.09(12) . . ? C6 N1 C5 108.76(11) . . ? N1 C5 C4 104.71(12) . . ? N1 C5 H5A 110.8 . . ? C4 C5 H5A 110.8 . . ? N1 C5 H5B 110.8 . . ? C4 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C5 C4 C3 105.45(13) . . ? C5 C4 H4A 110.7 . . ? C3 C4 H4A 110.7 . . ? C5 C4 H4B 110.7 . . ? C3 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? C2 C3 C4 105.18(12) . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3B 110.7 . . ? C4 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? N1 C2 C3 103.74(12) . . ? N1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? N1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C7 C6 N1 112.07(11) . . ? C7 C6 H6A 109.2 . . ? N1 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? N1 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 177.93(17) . . ? C7 C8 H8 180.0 . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 24.61 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.165 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.033 #===END