# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dhcl_120 _audit_creation_method SHELXL-97 _chemical_name_systematic '1,4diazabicyclo[2.2.2]octane hydrochloride' _chemical_name_common 'dabco hydrochloride' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H13 Cl N2' _chemical_formula_weight 148.63 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 orthorhombic _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 7.2633(2) _cell_length_b 10.06450(10) _cell_length_c 10.0786(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 736.76(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.431 _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 120.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5184 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 37.38 _reflns_number_total 1899 _reflns_number_gt 1828 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysalisPro _computing_cell_refinement CrysalisPro _computing_data_reduction CrysalisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0335P)^2^+0.0275P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_number_reflns 1899 _refine_ls_number_parameters 76 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0280 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0624 _refine_ls_wR_factor_gt 0.0610 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _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 0.0000 0.94065(2) 0.61192(2) 0.01836(6) Uani 1 2 d S . . N1 N 0.0000 0.55933(8) 0.87337(11) 0.01634(17) Uani 1 2 d S . . N2 N 0.0000 0.78003(9) 0.99484(9) 0.01520(17) Uani 1 2 d S . . C1 C 0.0000 0.53854(11) 1.01747(13) 0.0195(2) Uani 1 2 d S . . C2 C 0.0000 0.67016(11) 1.09450(12) 0.0203(2) Uani 1 2 d S . . C3 C 0.16421(14) 0.63662(8) 0.83767(10) 0.02222(17) Uani 1 1 d . . . C4 C 0.16894(12) 0.77055(7) 0.91006(9) 0.01874(16) Uani 1 1 d . . . H1 H 0.284(2) 0.7777(14) 0.9701(15) 0.037(4) Uiso 1 1 d . . . H2 H 0.166(2) 0.8516(12) 0.8534(16) 0.028(4) Uiso 1 1 d . . . H3 H 0.167(2) 0.6509(14) 0.7416(16) 0.035(4) Uiso 1 1 d . . . H4 H 0.279(2) 0.5810(14) 0.8617(15) 0.037(4) Uiso 1 1 d . . . H5 H 0.105(2) 0.6804(14) 1.1496(14) 0.036(4) Uiso 1 1 d . . . H6 H 0.0000 0.8668(19) 1.039(2) 0.028(5) Uiso 1 2 d S . . H7 H 0.1058(17) 0.4933(18) 1.0401(16) 0.036(4) 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 0.01866(11) 0.01504(9) 0.02138(12) 0.00494(10) 0.000 0.000 N1 0.0189(5) 0.0119(3) 0.0183(4) -0.0023(3) 0.000 0.000 N2 0.0186(4) 0.0110(3) 0.0159(4) -0.0022(3) 0.000 0.000 C1 0.0267(6) 0.0125(4) 0.0194(5) 0.0020(4) 0.000 0.000 C2 0.0294(6) 0.0167(4) 0.0149(5) 0.0001(3) 0.000 0.000 C3 0.0229(4) 0.0196(3) 0.0242(4) -0.0060(3) 0.0084(3) -0.0025(3) C4 0.0184(4) 0.0141(3) 0.0237(4) -0.0016(3) 0.0030(3) -0.0029(3) _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 C3 1.4687(11) . ? N1 C3 1.4687(11) 4 ? N1 C1 1.4674(17) . ? N2 C4 1.4983(10) 4 ? N2 C4 1.4983(10) . ? N2 C2 1.4939(15) . ? C1 C2 1.5354(16) . ? C3 C3 2.385(2) 4 ? C3 C4 1.5330(12) . ? C3 C4 2.8643(13) 4 ? C4 C4 2.4541(17) 4 ? C4 C3 2.8643(13) 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 _geom_angle_publ_flag C3 N1 C3 108.60(10) . 4 ? C3 N1 C1 108.54(7) . . ? C3 N1 C1 108.54(7) 4 . ? C4 N2 C4 109.96(9) 4 . ? C4 N2 C2 109.65(6) 4 . ? C4 N2 C2 109.65(6) . . ? N1 C1 C2 112.17(9) . . ? N2 C2 C1 107.38(9) . . ? N1 C3 C3 35.70(5) . 4 ? N1 C3 C4 111.55(7) . . ? C3 C3 C4 91.28(5) 4 . ? N1 C3 C4 60.05(5) . 4 ? C3 C3 C4 32.35(2) 4 4 ? C4 C3 C4 58.93(5) . 4 ? N2 C4 C4 35.02(5) . 4 ? N2 C4 C3 108.00(7) . . ? C4 C4 C3 88.72(5) 4 . ? N2 C4 C3 58.89(5) . 4 ? C4 C4 C3 32.35(2) 4 4 ? C3 C4 C3 56.37(6) . 4 ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 37.38 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.278 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 949831' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dsc1 _audit_creation_method SHELXL-97 _chemical_name_systematic '1,4diazabicyclo[2.2.2]octane hydrochloride' _chemical_name_common 'dabco hydrochloride' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H13 Cl N2' _chemical_formula_weight 148.63 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 orthorhombic _symmetry_space_group_name_H-M Cmc2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y, z+1/2' '-x, y, z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' _cell_length_a 7.368(6) _cell_length_b 10.076(2) _cell_length_c 10.227(5) _cell_angle_alpha 90.00(4) _cell_angle_beta 90.00(6) _cell_angle_gamma 90.00(6) _cell_volume 759.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.418 _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 295(1) _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 KM-4 _diffrn_measurement_method 'theta-two theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 897 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0210 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.05 _reflns_number_total 897 _reflns_number_gt 835 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4 program' _computing_cell_refinement 'KM4 program' _computing_data_reduction 'KM4 program' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0505P)^2^+0.0494P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.041(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.09(7) _refine_ls_number_reflns 897 _refine_ls_number_parameters 77 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0731 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.063 _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 0.0000 0.44452(5) 0.24678(5) 0.0446(2) Uani 1 2 d S . . N1 N 0.0000 0.94108(17) 0.4837(2) 0.0402(4) Uani 1 2 d S . . N2 N 0.0000 0.72096(18) 0.36707(16) 0.0363(4) Uani 1 2 d S . . C1 C 0.0000 0.8299(3) 0.2682(2) 0.0460(5) Uani 1 2 d S . . H1 H -0.103(3) 0.815(2) 0.211(2) 0.057(6) Uiso 1 1 d . . . C2 C 0.0000 0.9607(2) 0.3421(3) 0.0450(5) Uani 1 2 d S . . H2 H 0.092(3) 1.022(3) 0.316(3) 0.061(6) Uiso 1 1 d . . . C3 C 0.1616(3) 0.86454(17) 0.5194(2) 0.0501(4) Uani 1 1 d . . . H3A H 0.172(4) 0.842(2) 0.614(3) 0.071(7) Uiso 1 1 d . . . H3B H 0.270(4) 0.905(2) 0.504(3) 0.074(8) Uiso 1 1 d . . . C4 C 0.1657(2) 0.73136(17) 0.45030(17) 0.0442(4) Uani 1 1 d . . . H4A H 0.271(5) 0.731(3) 0.390(2) 0.066(7) Uiso 1 1 d . . . H4B H 0.153(4) 0.666(2) 0.510(3) 0.059(6) Uiso 1 1 d . . . H5 H 0.0000 0.653(3) 0.331(3) 0.041(7) Uiso 1 2 d 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0446(3) 0.0382(3) 0.0508(3) -0.0150(2) 0.000 0.000 N1 0.0475(10) 0.0286(8) 0.0443(9) -0.0078(6) 0.000 0.000 N2 0.0459(10) 0.0259(8) 0.0371(8) -0.0067(7) 0.000 0.000 C1 0.0636(13) 0.0421(11) 0.0324(12) 0.0005(8) 0.000 0.000 C2 0.0555(13) 0.0304(10) 0.0492(12) 0.0075(9) 0.000 0.000 C3 0.0531(10) 0.0432(9) 0.0539(10) -0.0118(8) -0.0173(8) 0.0012(7) C4 0.0459(9) 0.0331(8) 0.0537(10) -0.0024(7) -0.0060(7) 0.0073(6) _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 1.462(3) . ? N1 C3 1.465(3) 4 ? N1 C3 1.465(3) . ? N2 C4 1.492(2) . ? N2 C4 1.492(2) 4 ? N2 C1 1.492(3) . ? C1 C2 1.519(3) . ? C3 C4 1.517(2) . ? 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 C3 108.53(15) . 4 ? C2 N1 C3 108.53(15) . . ? C3 N1 C3 108.8(2) 4 . ? C4 N2 C4 109.82(18) . 4 ? C4 N2 C1 109.56(14) . . ? C4 N2 C1 109.56(14) 4 . ? N2 C1 C2 107.54(18) . . ? N1 C2 C1 112.06(18) . . ? N1 C3 C4 111.45(15) . . ? N2 C4 C3 108.17(15) . . ? 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 N2 H5 Cl1 0.77(3) 2.27(3) 3.045(2) 174(3) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.164 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 949832' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dcl_3h2ort _audit_creation_method SHELXL-97 _chemical_name_systematic '1,4diazabicyclo[2.2.2]octane hydrochloride trihydrate' _chemical_name_common 'dabco hydrochloride trihydrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H19 Cl N2 O3' _chemical_formula_weight 202.68 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' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmcm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 5.2847(2) _cell_length_b 17.0040(13) _cell_length_c 12.0194(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1080.06(13) _cell_formula_units_Z 4 _cell_measurement_temperature 295.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295.0(1) _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 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5267 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 32.19 _reflns_number_total 1032 _reflns_number_gt 616 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysalisPro _computing_cell_refinement CrysalisPro _computing_data_reduction CrysalisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1914P)^2^+0.1046P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1032 _refine_ls_number_parameters 56 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1248 _refine_ls_R_factor_gt 0.0920 _refine_ls_wR_factor_ref 0.3148 _refine_ls_wR_factor_gt 0.2768 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 N1 N 0.2380(3) 0.16145(12) 0.7500 0.0452(7) Uani 1 2 d SD . . C1 C 0.1443(5) 0.08011(15) 0.7500 0.0668(10) Uani 1 2 d S . . H1A H 0.222(7) 0.050(3) 0.811(3) 0.117(12) Uiso 1 1 d . . . C2 C 0.1450(4) 0.20334(17) 0.6505(2) 0.0696(8) Uani 1 1 d . . . H2A H 0.207(6) 0.190(2) 0.583(3) 0.089(9) Uiso 1 1 d . . . H2B H 0.229(7) 0.254(3) 0.640(3) 0.102(10) Uiso 1 1 d . . . Cl1 Cl 0.0000 0.124(2) 0.369(6) 0.133(4) Uani 0.25 2 d SP . . O1 O 0.0000 0.1084(18) 0.367(5) 0.133(4) Uani 0.75 2 d SP . . O2 O 0.0000 0.426(3) 0.550(4) 0.128(4) Uani 0.75 2 d SP . . Cl2 Cl 0.0000 0.415(3) 0.543(4) 0.128(4) Uani 0.25 2 d SP . . H1 H -0.25(2) 0.403(7) 0.591(8) 0.154 Uiso 0.50 1 d P . . H3 H 0.394(7) 0.163(7) 0.7500 0.154 Uiso 0.50 2 d SPD . . H4 H 0.0000 0.5000 0.5000 0.154 Uiso 1 4 d S . . H5 H 0.0000 0.103(6) 0.2500 0.154 Uiso 1 4 d 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0221(8) 0.0486(11) 0.0650(13) 0.000 0.000 -0.0008(6) C1 0.0323(11) 0.0466(14) 0.122(3) 0.000 0.000 0.0042(9) C2 0.0388(10) 0.0896(17) 0.0804(16) 0.0282(12) 0.0056(9) -0.0043(9) Cl1 0.116(2) 0.098(11) 0.186(4) -0.031(9) 0.000 0.000 O1 0.116(2) 0.098(11) 0.186(4) -0.031(9) 0.000 0.000 O2 0.0943(17) 0.158(11) 0.133(5) -0.025(5) 0.000 0.000 Cl2 0.0943(17) 0.158(11) 0.133(5) -0.025(5) 0.000 0.000 _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 1.469(3) . ? N1 C2 1.476(3) . ? N1 C2 1.476(3) 10_557 ? C1 C1 1.525(5) 3_556 ? C2 C2 1.533(4) 12 ? 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 109.99(15) . . ? C1 N1 C2 109.99(15) . 10_557 ? C2 N1 C2 108.2(3) . 10_557 ? N1 C1 C1 109.71(11) . 3_556 ? N1 C2 C2 109.45(9) . 12 ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 32.19 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.402 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 949833' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cmcm270 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H19 Cl N2 O3' _chemical_formula_weight 202.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 5.313(3) _cell_length_b 16.988(11) _cell_length_c 12.159(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1097.3(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 58 _exptl_absorpt_coefficient_mu 0.000 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.83700 _diffrn_radiation_type ? _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1813 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 30.01 _reflns_number_total 571 _reflns_number_gt 429 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0578P)^2^+1.8445P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 571 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _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 N1 N 0.2382(3) 0.15957(9) 0.7500 0.0510(6) Uani 1 2 d S . . C1 C 0.1444(6) 0.07863(17) 0.7500 0.0744(11) Uani 1 2 d S . . C2 C 0.1450(4) 0.20201(17) 0.6523(2) 0.0768(9) Uani 1 1 d . . . Cl1 Cl 0.0000 0.1181(8) 0.3678(10) 0.132(4) Uani 0.25 2 d SP . . O1 O 0.0000 0.1181(8) 0.3678(10) 0.132(4) Uani 0.75 2 d SP . . O2 O 0.0000 0.4197(7) 0.5453(12) 0.121(3) Uani 0.75 2 d SP . . Cl2 Cl 0.0000 0.4197(7) 0.5453(12) 0.121(3) Uani 0.25 2 d SP . . H1 H 0.234(5) 0.0397(10) 0.697(3) 0.105(9) Uani 0.50 1 d P . . H1A H 0.200(5) 0.0611(12) 0.659(3) 0.104(6) Uani 0.50 1 d P . . H2 H 0.232(4) 0.1864(18) 0.580(2) 0.150(12) Uani 0.50 1 d P . . H2A H 0.204(4) 0.1606(13) 0.5837(10) 0.116(8) Uani 0.50 1 d P . . H3 H 0.2127(12) 0.2602(4) 0.6548(7) 0.135(2) Uani 1 1 d . . . H4 H 0.5000 0.1590(5) 0.7500 0.100(3) Uani 1 4 d S . . H5 H -0.139(4) 0.4081(12) 0.573(2) 0.157(8) Uani 0.50 1 d P . . H6 H -0.131(2) 0.1055(11) 0.3880(18) 0.118(5) Uani 0.50 1 d P . . H7 H 0.0000 0.110(2) 0.307(3) 0.147(15) Uani 0.50 2 d SP . . H8 H 0.0000 0.4609(17) 0.526(4) 0.15(2) Uani 0.50 2 d SP . . 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 N1 0.0322(8) 0.0519(9) 0.0688(10) 0.000 0.000 0.0002(7) C1 0.0406(15) 0.0395(16) 0.143(4) 0.000 0.000 0.0057(12) C2 0.0438(12) 0.1019(18) 0.0845(17) 0.0343(14) 0.0075(12) -0.0015(10) Cl1 0.144(11) 0.106(5) 0.147(9) -0.028(5) 0.000 0.000 O1 0.144(11) 0.106(5) 0.147(9) -0.028(5) 0.000 0.000 O2 0.085(5) 0.149(9) 0.129(5) -0.004(8) 0.000 0.000 Cl2 0.085(5) 0.149(9) 0.129(5) -0.004(8) 0.000 0.000 H1 0.072(6) 0.054(6) 0.19(3) -0.041(9) -0.001(10) 0.027(5) H1A 0.074(11) 0.078(12) 0.160(19) -0.031(11) 0.024(10) 0.004(8) H2 0.061(7) 0.25(3) 0.140(16) 0.119(17) 0.034(8) 0.028(11) H2A 0.101(11) 0.207(18) 0.041(5) -0.023(9) 0.017(5) -0.003(10) H3 0.089(4) 0.103(4) 0.212(7) 0.073(4) -0.007(4) -0.014(3) H4 0.140(9) 0.077(5) 0.083(5) 0.000 0.000 0.000 H5 0.17(2) 0.127(11) 0.174(17) 0.002(10) -0.043(17) -0.026(15) H6 0.058(10) 0.126(9) 0.170(13) -0.055(9) 0.010(9) 0.005(7) H7 0.13(2) 0.083(10) 0.23(5) -0.027(19) 0.000 0.000 H8 0.096(14) 0.17(3) 0.19(5) -0.10(4) 0.000 0.000 _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 1.463(3) . ? N1 C2 1.475(2) 10_557 ? N1 C2 1.475(2) . ? C1 C1 1.535(6) 3_556 ? C2 C2 1.540(5) 12 ? 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 110.18(15) . 10_557 ? C1 N1 C2 110.18(15) . . ? C2 N1 C2 107.3(3) 10_557 . ? N1 C1 C1 109.92(13) . 3_556 ? N1 C2 C2 109.63(11) . 12 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.458 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 949834' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dcl_150 _audit_creation_method SHELXL-97 _chemical_name_systematic '1,4diazabicyclo[2.2.2]octane hydrochloride' _chemical_name_common 'dabco hydrochloride' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H19 Cl N2 O3' _chemical_formula_weight 202.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' 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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 16.488(3) _cell_length_b 5.2695(11) _cell_length_c 12.254(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.28(3) _cell_angle_gamma 90.00 _cell_volume 1063.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 3.027 _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 150.0(1) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini A Ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5570 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 68.70 _reflns_number_total 1088 _reflns_number_gt 1034 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysalisPro _computing_cell_refinement CrysalisPro _computing_data_reduction CrysalisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1128P)^2^+6.3865P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1088 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1010 _refine_ls_R_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.2744 _refine_ls_wR_factor_gt 0.2734 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.203 _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 Cl4 Cl 0.36916(16) 0.0000 0.8523(2) 0.0466(8) Uani 0.40 2 d SP . . O4 O 0.36916(16) 0.0000 0.8523(2) 0.0466(8) Uani 0.60 2 d SP . . O1 O 0.4324(3) 0.5000 0.9231(4) 0.0665(14) Uani 0.90 2 d SP . . Cl1 Cl 0.4324(3) 0.5000 0.9231(4) 0.0665(14) Uani 0.10 2 d SP . . N1 N 0.3469(2) 0.2381(6) 1.2428(3) 0.0302(9) Uani 1 1 d . . . H1N H 0.348(6) 0.38(2) 1.246(7) 0.036 Uiso 0.50 1 d P . . C1 C 0.2900(3) 0.1447(7) 1.3243(4) 0.0347(10) Uani 1 1 d . . . H1A H 0.233(3) 0.221(10) 1.299(3) 0.042 Uiso 1 1 d . . . H1B H 0.312(3) 0.202(10) 1.394(4) 0.042 Uiso 1 1 d . . . C2 C 0.4300(2) 0.1448(8) 1.2720(5) 0.0410(11) Uani 1 1 d . . . H2A H 0.443(3) 0.186(11) 1.344(4) 0.049 Uiso 1 1 d . . . H2B H 0.462(3) 0.202(12) 1.218(4) 0.049 Uiso 1 1 d . . . C3 C 0.3203(4) 0.1464(9) 1.1336(4) 0.0438(12) Uani 1 1 d . . . H3A H 0.354(3) 0.215(12) 1.085(4) 0.053 Uiso 1 1 d . . . H3B H 0.270(4) 0.175(12) 1.122(4) 0.053 Uiso 1 1 d . . . O2 O 0.0917(2) 0.0000 0.4674(3) 0.0703(11) Uani 0.60 2 d SP . . Cl2 Cl 0.0917(2) 0.0000 0.4674(3) 0.0703(11) Uani 0.40 2 d SP . . O3 O 0.3865(3) 0.0000 0.6082(5) 0.086(2) Uani 0.90 2 d SP . . Cl3 Cl 0.3865(3) 0.0000 0.6082(5) 0.086(2) Uani 0.10 2 d SP . . 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 Cl4 0.0419(14) 0.0354(14) 0.0631(17) 0.000 0.0074(11) 0.000 O4 0.0419(14) 0.0354(14) 0.0631(17) 0.000 0.0074(11) 0.000 O1 0.087(4) 0.036(2) 0.076(3) 0.000 0.008(3) 0.000 Cl1 0.087(4) 0.036(2) 0.076(3) 0.000 0.008(3) 0.000 N1 0.0314(17) 0.0123(15) 0.0472(19) 0.0000(14) 0.0067(13) 0.0019(13) C1 0.037(2) 0.020(2) 0.048(2) -0.0013(17) 0.0092(17) 0.0010(17) C2 0.030(2) 0.020(2) 0.073(3) -0.004(2) 0.0059(19) -0.0007(17) C3 0.060(3) 0.027(3) 0.044(2) 0.0022(19) 0.002(2) 0.005(2) O2 0.090(3) 0.0452(19) 0.075(2) 0.000 -0.0137(18) 0.000 Cl2 0.090(3) 0.0452(19) 0.075(2) 0.000 -0.0137(18) 0.000 O3 0.056(3) 0.122(6) 0.079(3) 0.000 0.007(2) 0.000 Cl3 0.056(3) 0.122(6) 0.079(3) 0.000 0.007(2) 0.000 _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 C3 1.473(6) . ? N1 C1 1.480(5) . ? N1 C2 1.487(5) . ? C1 C1 1.525(8) 6 ? C2 C2 1.526(8) 6 ? C3 C3 1.543(9) 6 ? 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 C3 N1 C1 109.3(4) . . ? C3 N1 C2 110.4(4) . . ? C1 N1 C2 109.3(3) . . ? N1 C1 C1 109.4(2) . 6 ? N1 C2 C2 109.3(2) . 6 ? N1 C3 C3 109.1(2) . 6 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 68.70 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.840 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 949835'