# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/369 data_3a # 1. SUBMISSION DETAILS for compound 3a _publ_contact_author ; Toupet Loic G.M.C.M.-UMR6626 Universite de Rennes Campus de Beaulieu 35042 RENNES cedex , FRANCE ; _publ_contact_author_email 'toupet@univ-rennes1.fr' _publ_contact_author_fax '(33) 2 99 28 67 17' _publ_contact_author_phone '(33) 2 99 28 60 65' # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # 3. TITLE AND AUTHOR LIST _publ_section_title ;Cis-diprotected cyclam and cyclen : a new route to symmetrically or dissymmetrically 1,4-disubstituted tetraazamacrocycles and to dissymmetrically tetrasubstituted derivatives. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Frederic Bellouard' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Francoise Chuburu' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Nelly Kervarec' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Loic Toupet' #<--'Last name, first name' ; G.M.C.M.-UMR6626 Universite de Rennes Campus de Beaulieu 35042 RENNES cedex , FRANCE ; 'Smail Triki' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Yves Le Mest' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Henri Handel' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_experimental ; Backgrounds were obtained from analysis of the scan profile (Blessing, Coppens _& Becker, 1974) ; _publ_section_references ; Blessing, R.H., Coppens, P. & Becker, P. (1974). J. Appl. Cryst., 7, 488-492. Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. Enraf-Nonius, CAD4 Operations Manual, Delft, 1977. Fair, C.K. (1990). MolEN, An Interactive Intelligent System for Crystal Structure Analysis, User Manual, Enraf - Nonius, Delft, The Netherlands. International Tables for X-Ray Crystallography, Vol. IV, The Kynoch Press, Birmingham, England, 1974 Johnson, C.K. (1976). ORTEP. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Zachariasen, W.H. (1963). Acta Crystallogr., 16, 1139-1144. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 N2 O2' _chemical_formula_weight 154.17 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 7.190(8) _cell_length_b 8.080(4) _cell_length_c 12.279(12) _cell_angle_alpha 90.00 _cell_angle_beta 102.40(9) _cell_angle_gamma 90.00 _cell_volume 696.7(11) _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 prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.110 _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 0.71069 _diffrn_radiation_type MoK\a _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 1550 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.1663 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 27.00 _reflns_number_total 1440 _reflns_number_gt 600 _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^)+(0.1207P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.065(16) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1440 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2322 _refine_ls_R_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.2392 _refine_ls_wR_factor_gt 0.1810 _refine_ls_goodness_of_fit_ref 0.973 _refine_ls_restrained_S_all 0.973 _refine_ls_shift/su_max 0.004 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2963(5) 0.1718(5) -0.1286(3) 0.0466(12) Uani 1 1 d . . . O2 O 0.0140(6) -0.0122(5) -0.2524(3) 0.0582(12) Uani 1 1 d . . . N1 N -0.1953(6) 0.0884(6) -0.1549(3) 0.0336(11) Uani 1 1 d . . . N2 N 0.1086(6) 0.2290(5) -0.0069(3) 0.0320(11) Uani 1 1 d . . . C2 C 0.3529(8) 0.0193(7) 0.2063(4) 0.0384(14) Uani 1 1 d . . . H2A H 0.4620 -0.0487 0.2386 0.033(13) Uiso 1 1 calc R . . H2B H 0.3168 0.0809 0.2663 0.042(14) Uiso 1 1 calc R . . C3 C 0.4107(7) 0.1405(7) 0.1250(4) 0.0371(14) Uani 1 1 d . . . H3A H 0.4343 0.0776 0.0621 0.040(14) Uiso 1 1 calc R . . H3B H 0.5307 0.1902 0.1615 0.028(13) Uiso 1 1 calc R . . C4 C 0.2739(8) 0.2801(7) 0.0793(4) 0.0398(14) Uani 1 1 d . . . H4A H 0.2284 0.3299 0.1406 0.033(14) Uiso 1 1 calc R . . H4B H 0.3434 0.3645 0.0482 0.07(2) Uiso 1 1 calc R . . C5 C 0.1390(7) 0.1714(6) -0.1048(4) 0.0302(12) Uani 1 1 d . . . C6 C -0.0227(8) 0.0788(7) -0.1802(4) 0.0372(14) Uani 1 1 d . . . C7 C -0.2289(8) 0.2323(8) -0.0884(5) 0.0507(17) Uani 1 1 d . . . H7A H -0.2363 0.3312 -0.1339 0.15(4) Uiso 1 1 calc R . . H7B H -0.3504 0.2189 -0.0671 0.019(12) Uiso 1 1 calc R . . C8 C -0.0811(8) 0.2538(8) 0.0112(5) 0.0484(17) Uani 1 1 d . . . H8A H -0.0900 0.3648 0.0398 0.07(2) Uiso 1 1 calc R . . H8B H -0.1029 0.1765 0.0676 0.08(2) 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 O1 0.044(3) 0.058(3) 0.042(2) 0.0132(18) 0.0203(19) 0.009(2) O2 0.070(3) 0.062(3) 0.051(2) -0.027(2) 0.032(2) -0.006(3) N1 0.032(2) 0.034(3) 0.035(2) -0.003(2) 0.0098(19) 0.001(2) N2 0.034(2) 0.031(3) 0.035(2) -0.0020(19) 0.014(2) 0.0005(19) C2 0.050(3) 0.036(3) 0.029(2) -0.005(2) 0.006(2) 0.005(3) C3 0.037(3) 0.038(3) 0.037(3) -0.010(2) 0.009(2) -0.002(3) C4 0.039(3) 0.034(3) 0.046(3) -0.004(3) 0.010(3) 0.000(3) C5 0.029(3) 0.028(3) 0.035(3) 0.012(2) 0.010(2) 0.003(2) C6 0.051(4) 0.032(3) 0.033(3) 0.006(2) 0.019(3) 0.003(3) C7 0.035(3) 0.057(4) 0.062(4) -0.020(3) 0.014(3) 0.005(3) C8 0.038(3) 0.061(5) 0.045(3) -0.017(3) 0.008(3) 0.009(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 O1 C5 1.227(6) . ? O2 C6 1.223(6) . ? N1 C6 1.344(6) . ? N1 C2 1.460(6) 3 ? N1 C7 1.471(7) . ? N2 C5 1.350(6) . ? N2 C8 1.442(6) . ? N2 C4 1.471(6) . ? C2 N1 1.460(6) 3 ? C2 C3 1.518(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.522(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.519(7) . ? C7 C8 1.448(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 C6 N1 C2 122.4(4) . 3 ? C6 N1 C7 116.3(5) . . ? C2 N1 C7 120.4(4) 3 . ? C5 N2 C8 121.7(4) . . ? C5 N2 C4 118.5(4) . . ? C8 N2 C4 119.7(4) . . ? N1 C2 C3 113.4(4) 3 . ? N1 C2 H2A 108.9 3 . ? C3 C2 H2A 108.9 . . ? N1 C2 H2B 108.9 3 . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 118.3(4) . . ? C2 C3 H3A 107.7 . . ? C4 C3 H3A 107.7 . . ? C2 C3 H3B 107.7 . . ? C4 C3 H3B 107.7 . . ? H3A C3 H3B 107.1 . . ? N2 C4 C3 114.5(4) . . ? N2 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? N2 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? O1 C5 N2 123.0(5) . . ? O1 C5 C6 118.7(5) . . ? N2 C5 C6 117.6(4) . . ? O2 C6 N1 123.7(5) . . ? O2 C6 C5 118.8(5) . . ? N1 C6 C5 117.1(4) . . ? C8 C7 N1 112.7(5) . . ? C8 C7 H7A 109.1 . . ? N1 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? N1 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? N2 C8 C7 113.6(5) . . ? N2 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? N2 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? 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 C2 C3 C4 69.2(6) 3 . . . ? C5 N2 C4 C3 -64.8(6) . . . . ? C8 N2 C4 C3 120.2(5) . . . . ? C2 C3 C4 N2 -75.6(6) . . . . ? C8 N2 C5 O1 169.0(5) . . . . ? C4 N2 C5 O1 -5.9(8) . . . . ? C8 N2 C5 C6 -20.7(7) . . . . ? C4 N2 C5 C6 164.5(4) . . . . ? C2 N1 C6 O2 4.8(8) 3 . . . ? C7 N1 C6 O2 -164.5(5) . . . . ? C2 N1 C6 C5 -167.7(4) 3 . . . ? C7 N1 C6 C5 23.1(7) . . . . ? O1 C5 C6 O2 10.6(7) . . . . ? N2 C5 C6 O2 -160.2(5) . . . . ? O1 C5 C6 N1 -176.5(4) . . . . ? N2 C5 C6 N1 12.7(7) . . . . ? C6 N1 C7 C8 -51.4(7) . . . . ? C2 N1 C7 C8 139.1(5) 3 . . . ? C5 N2 C8 C7 -7.6(8) . . . . ? C4 N2 C8 C7 167.2(5) . . . . ? N1 C7 C8 N2 42.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.409 _refine_diff_density_min -0.456 _refine_diff_density_rms 0.110 #===END data_4b # 1. SUBMISSION DETAILS for compound 4b _publ_contact_author ; Toupet Loic G.M.C.M.-UMR6626 Universite de Rennes Campus de Beaulieu 35042 RENNES cedex , FRANCE ; _publ_contact_author_email 'toupet@univ-rennes1.fr' _publ_contact_author_fax '(33) 2 99 28 67 17' _publ_contact_author_phone '(33) 2 99 28 60 65' _publ_section_title ;Cis-diprotected cyclam and cyclen : a new route to symmetrically or dissymmetrically 1,4-disubstituted tetraazamacrocycles and to dissymmetrically tetrasubstituted derivatives. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Frederic Bellouard' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Francoise Chuburu' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Nelly Kervarec' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Loic Toupet' #<--'Last name, first name' ; G.M.C.M.-UMR6626 Universite de Rennes Campus de Beaulieu 35042 RENNES cedex , FRANCE ; 'Smail Triki' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Yves Le Mest' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; 'Henri Handel' #<--'Last name, first name' ; UMR CNRS 6521, 6 avenue Le Gorgeu, BP 809, 29285 BREST cedex France ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 N4 O2, H2O' _chemical_formula_weight 415.52 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 13.465(3) _cell_length_b 12.608(4) _cell_length_c 14.504(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.85(3) _cell_angle_gamma 90.00 _cell_volume 2196.9(10) _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 prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.084 _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 0.71069 _diffrn_radiation_type MoK\a _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 5000 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.02 _reflns_number_total 4793 _reflns_number_gt 2946 _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^)+(0.0729P)^2^+0.3772P] 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 SHELXL _refine_ls_extinction_coef 0.0034(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4793 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1005 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1505 _refine_ls_wR_factor_gt 0.1304 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.85928(13) 0.33968(13) 0.91144(14) 0.0791(5) Uani 1 1 d . . . O2 O 0.94835(11) 0.14216(13) 0.95633(13) 0.0738(5) Uani 1 1 d . . . O3 O 0.5589(4) 0.0473(4) 1.0822(4) 0.1316(17) Uani 0.50 1 d P . . N1 N 0.70599(13) 0.28252(13) 0.92246(13) 0.0547(4) Uani 1 1 d . . . N2 N 0.78297(12) 0.07796(12) 0.93424(12) 0.0499(4) Uani 1 1 d . . . N3 N 0.66302(12) 0.02095(12) 0.71801(12) 0.0472(4) Uani 1 1 d . . . N4 N 0.53691(12) 0.23860(11) 0.70419(12) 0.0462(4) Uani 1 1 d . . . C1 C 0.80814(16) 0.27046(17) 0.93107(15) 0.0556(5) Uani 1 1 d . . . C2 C 0.85485(15) 0.15702(16) 0.94806(15) 0.0523(5) Uani 1 1 d . . . C3 C 0.67255(16) 0.09503(16) 0.92806(17) 0.0557(5) Uani 1 1 d . . . H3A H 0.6583 0.0411 0.9683 0.067 Uiso 1 1 calc R . . H3B H 0.6165 0.0882 0.8568 0.067 Uiso 1 1 calc R . . C4 C 0.66390(18) 0.20142(17) 0.96740(17) 0.0604(5) Uani 1 1 d . . . H4A H 0.5867 0.2163 0.9500 0.072 Uiso 1 1 calc R . . H4B H 0.7064 0.2027 1.0421 0.072 Uiso 1 1 calc R . . C5 C 0.80173(16) -0.02486(15) 0.89745(16) 0.0568(5) Uani 1 1 d . . . H5A H 0.7544 -0.0780 0.9058 0.068 Uiso 1 1 calc R . . H5B H 0.8786 -0.0463 0.9384 0.068 Uiso 1 1 calc R . . C6 C 0.77648(15) -0.01814(16) 0.78467(16) 0.0558(5) Uani 1 1 d . . . H6A H 0.8299 0.0289 0.7781 0.067 Uiso 1 1 calc R . . H6B H 0.7852 -0.0879 0.7611 0.067 Uiso 1 1 calc R . . C7 C 0.66357(16) 0.12048(15) 0.66604(16) 0.0517(5) Uani 1 1 d . . . H7A H 0.6800 0.1043 0.6090 0.062 Uiso 1 1 calc R . . H7B H 0.7237 0.1645 0.7143 0.062 Uiso 1 1 calc R . . C8 C 0.55652(15) 0.18466(15) 0.62445(15) 0.0496(4) Uani 1 1 d . . . H8A H 0.5585 0.2373 0.5766 0.060 Uiso 1 1 calc R . . H8B H 0.4944 0.1377 0.5860 0.060 Uiso 1 1 calc R . . C9 C 0.60414(17) 0.33551(14) 0.74129(16) 0.0532(5) Uani 1 1 d . . . H9A H 0.5636 0.3942 0.6971 0.064 Uiso 1 1 calc R . . H9B H 0.6725 0.3265 0.7352 0.064 Uiso 1 1 calc R . . C10 C 0.63334(18) 0.36359(15) 0.85254(17) 0.0595(5) Uani 1 1 d . . . H10A H 0.6706 0.4318 0.8698 0.071 Uiso 1 1 calc R . . H10B H 0.5658 0.3689 0.8605 0.071 Uiso 1 1 calc R . . C11 C 0.59524(18) -0.06047(16) 0.64485(16) 0.0596(5) Uani 1 1 d . . . H11A H 0.6307 -0.0813 0.6024 0.071 Uiso 1 1 calc R . . H11B H 0.5230 -0.0307 0.5996 0.071 Uiso 1 1 calc R . . C12 C 0.57888(16) -0.15749(15) 0.69724(16) 0.0551(5) Uani 1 1 d . . . C13 C 0.6168(2) -0.25595(17) 0.6872(2) 0.0731(7) Uani 1 1 d . . . H13 H 0.6550 -0.2634 0.6478 0.088 Uiso 1 1 calc R . . C14 C 0.5992(2) -0.34392(18) 0.7347(2) 0.0815(8) Uani 1 1 d . . . H14 H 0.6257 -0.4097 0.7269 0.098 Uiso 1 1 calc R . . C15 C 0.54372(19) -0.33560(18) 0.7924(2) 0.0702(6) Uani 1 1 d . . . H15 H 0.5312 -0.3953 0.8233 0.084 Uiso 1 1 calc R . . C16 C 0.5066(2) -0.23878(19) 0.8047(2) 0.0733(6) Uani 1 1 d . . . H16 H 0.4694 -0.2320 0.8450 0.088 Uiso 1 1 calc R . . C17 C 0.52398(19) -0.15066(17) 0.7576(2) 0.0682(6) Uani 1 1 d . . . H17 H 0.4981 -0.0850 0.7667 0.082 Uiso 1 1 calc R . . C18 C 0.41936(16) 0.26761(16) 0.6666(2) 0.0666(6) Uani 1 1 d . . . H18A H 0.4000 0.3198 0.6120 0.080 Uiso 1 1 calc R . . H18B H 0.4104 0.3009 0.7227 0.080 Uiso 1 1 calc R . . C19 C 0.33941(15) 0.17699(16) 0.62631(17) 0.0550(5) Uani 1 1 d . . . C20 C 0.34891(11) 0.08975(12) 0.68719(13) 0.0691(6) Uani 1 1 d . . . H20 H 0.4059 0.0869 0.7544 0.083 Uiso 1 1 calc R . . C21 C 0.27529(11) 0.00755(12) 0.64963(13) 0.0953(9) Uani 1 1 d R . . H21 H 0.2881 -0.0547 0.6944 0.114 Uiso 1 1 d R . . C22 C 0.19050(11) 0.00777(12) 0.55798(13) 0.1039(11) Uani 1 1 d R . . H22 H 0.1354 -0.0529 0.5297 0.125 Uiso 1 1 d R . . C23 C 0.17702(11) 0.09130(12) 0.49357(13) 0.1084(12) Uani 1 1 d R . . H23 H 0.1183 0.0913 0.4272 0.130 Uiso 1 1 calc R . . C24 C 0.2522(2) 0.1782(2) 0.5275(2) 0.0820(7) Uani 1 1 d . . . H24 H 0.2429 0.2353 0.4838 0.098 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 O1 0.0609(9) 0.0662(10) 0.0967(12) 0.0102(9) 0.0238(9) -0.0179(8) O2 0.0402(7) 0.0793(11) 0.0959(12) 0.0004(9) 0.0255(7) -0.0015(7) O3 0.154(4) 0.112(3) 0.160(4) 0.020(3) 0.099(4) 0.022(3) N1 0.0535(10) 0.0484(9) 0.0576(10) 0.0021(8) 0.0211(8) 0.0039(7) N2 0.0395(8) 0.0500(9) 0.0536(9) 0.0041(7) 0.0151(7) 0.0041(7) N3 0.0414(8) 0.0423(8) 0.0539(9) 0.0008(7) 0.0180(7) 0.0020(6) N4 0.0423(8) 0.0381(8) 0.0566(9) 0.0038(7) 0.0209(7) 0.0031(6) C1 0.0478(10) 0.0560(12) 0.0521(11) -0.0002(9) 0.0128(9) -0.0065(9) C2 0.0378(9) 0.0608(12) 0.0489(11) 0.0024(9) 0.0114(8) -0.0019(9) C3 0.0478(10) 0.0547(11) 0.0677(13) 0.0072(10) 0.0288(9) -0.0008(9) C4 0.0549(12) 0.0650(13) 0.0643(13) 0.0061(10) 0.0295(10) 0.0059(10) C5 0.0429(10) 0.0468(11) 0.0719(14) 0.0115(9) 0.0182(9) 0.0106(8) C6 0.0452(10) 0.0487(11) 0.0705(13) 0.0001(10) 0.0234(9) 0.0090(8) C7 0.0496(10) 0.0482(10) 0.0613(12) 0.0012(9) 0.0287(9) 0.0002(8) C8 0.0485(10) 0.0493(10) 0.0492(11) 0.0060(8) 0.0205(9) 0.0007(8) C9 0.0517(10) 0.0384(9) 0.0627(13) 0.0080(9) 0.0199(9) 0.0003(8) C10 0.0593(12) 0.0406(10) 0.0698(14) -0.0011(9) 0.0213(10) 0.0032(9) C11 0.0637(12) 0.0524(12) 0.0549(12) -0.0029(9) 0.0199(10) -0.0029(10) C12 0.0520(11) 0.0468(11) 0.0546(12) -0.0034(9) 0.0138(9) -0.0049(9) C13 0.0903(17) 0.0525(13) 0.0843(17) -0.0077(12) 0.0463(14) -0.0003(12) C14 0.0984(19) 0.0447(12) 0.103(2) -0.0027(12) 0.0474(17) 0.0017(12) C15 0.0660(14) 0.0531(13) 0.0777(16) 0.0057(11) 0.0202(12) -0.0090(11) C16 0.0643(13) 0.0677(15) 0.0893(17) 0.0040(13) 0.0359(13) -0.0049(11) C17 0.0637(13) 0.0510(12) 0.0901(17) 0.0025(11) 0.0350(12) 0.0045(10) C18 0.0473(11) 0.0483(11) 0.0991(17) 0.0030(11) 0.0284(11) 0.0068(9) C19 0.0395(9) 0.0569(12) 0.0683(13) -0.0056(10) 0.0240(9) 0.0060(8) C20 0.0507(11) 0.0626(13) 0.0875(16) 0.0019(12) 0.0255(11) 0.0005(10) C21 0.0629(15) 0.0662(16) 0.158(3) -0.0075(17) 0.0506(18) -0.0083(13) C22 0.0749(18) 0.095(2) 0.139(3) -0.048(2) 0.046(2) -0.0211(17) C23 0.0604(15) 0.172(3) 0.0756(19) -0.054(2) 0.0157(13) -0.015(2) C24 0.0629(14) 0.113(2) 0.0685(16) -0.0022(15) 0.0286(13) 0.0096(14) _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 O1 C1 1.222(2) . ? O2 C2 1.224(2) . ? N1 C1 1.332(3) . ? N1 C4 1.458(3) . ? N1 C10 1.461(3) . ? N2 C2 1.340(2) . ? N2 C3 1.464(2) . ? N2 C5 1.467(3) . ? N3 C11 1.462(2) . ? N3 C7 1.466(2) . ? N3 C6 1.476(2) . ? N4 C8 1.465(2) . ? N4 C18 1.469(2) . ? N4 C9 1.470(2) . ? C1 C2 1.537(3) . ? C3 C4 1.483(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.515(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.520(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.520(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.508(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.375(3) . ? C12 C17 1.380(3) . ? C13 C14 1.382(3) . ? C13 H13 0.9300 . ? C14 C15 1.354(4) . ? C14 H14 0.9300 . ? C15 C16 1.361(3) . ? C15 H15 0.9300 . ? C16 C17 1.379(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.496(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.380(3) . ? C19 C24 1.383(3) . ? C20 C21 1.3659 . ? C20 H20 0.9300 . ? C21 C22 1.3038 . ? C21 H21 0.9826 . ? C22 C23 1.3643 . ? C22 H22 1.0139 . ? C23 C24 1.420(3) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? 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 C4 118.12(17) . . ? C1 N1 C10 118.96(18) . . ? C4 N1 C10 121.83(17) . . ? C2 N2 C3 123.00(16) . . ? C2 N2 C5 118.72(16) . . ? C3 N2 C5 116.39(15) . . ? C11 N3 C7 111.98(15) . . ? C11 N3 C6 111.30(15) . . ? C7 N3 C6 112.26(15) . . ? C8 N4 C18 111.78(16) . . ? C8 N4 C9 111.97(15) . . ? C18 N4 C9 108.12(14) . . ? O1 C1 N1 124.3(2) . . ? O1 C1 C2 117.97(19) . . ? N1 C1 C2 116.85(17) . . ? O2 C2 N2 122.84(19) . . ? O2 C2 C1 119.11(18) . . ? N2 C2 C1 116.92(16) . . ? N2 C3 C4 111.31(16) . . ? N2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? N2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N1 C4 C3 110.39(17) . . ? N1 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? N1 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? N2 C5 C6 110.60(15) . . ? N2 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N3 C6 C5 112.78(16) . . ? N3 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? N3 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? N3 C7 C8 115.84(15) . . ? N3 C7 H7A 108.3 . . ? C8 C7 H7A 108.3 . . ? N3 C7 H7B 108.3 . . ? C8 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? N4 C8 C7 114.24(16) . . ? N4 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? N4 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? N4 C9 C10 113.79(16) . . ? N4 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? N4 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? N1 C10 C9 110.19(16) . . ? N1 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N1 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? N3 C11 C12 112.90(17) . . ? N3 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N3 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C17 117.0(2) . . ? C13 C12 C11 122.2(2) . . ? C17 C12 C11 120.74(19) . . ? C12 C13 C14 121.1(2) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 120.9(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 119.2(2) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 121.6(2) . . ? C16 C17 H17 119.2 . . ? C12 C17 H17 119.2 . . ? N4 C18 C19 114.81(16) . . ? N4 C18 H18A 108.6 . . ? C19 C18 H18A 108.6 . . ? N4 C18 H18B 108.6 . . ? C19 C18 H18B 108.6 . . ? H18A C18 H18B 107.5 . . ? C20 C19 C24 117.5(2) . . ? C20 C19 C18 121.09(18) . . ? C24 C19 C18 121.4(2) . . ? C21 C20 C19 120.58(10) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 123.3 . . ? C22 C21 H21 119.2 . . ? C20 C21 H21 117.6 . . ? C21 C22 C23 119.0 . . ? C21 C22 H22 123.7 . . ? C23 C22 H22 117.3 . . ? C22 C23 C24 120.28(13) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C19 C24 C23 119.3(2) . . ? C19 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? 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 C4 N1 C1 O1 -168.1(2) . . . . ? C10 N1 C1 O1 23.6(3) . . . . ? C4 N1 C1 C2 23.1(3) . . . . ? C10 N1 C1 C2 -145.20(18) . . . . ? C3 N2 C2 O2 177.72(19) . . . . ? C5 N2 C2 O2 -18.5(3) . . . . ? C3 N2 C2 C1 -14.6(3) . . . . ? C5 N2 C2 C1 149.25(17) . . . . ? O1 C1 C2 O2 10.4(3) . . . . ? N1 C1 C2 O2 179.94(19) . . . . ? O1 C1 C2 N2 -157.75(19) . . . . ? N1 C1 C2 N2 11.7(3) . . . . ? C2 N2 C3 C4 -15.9(3) . . . . ? C5 N2 C3 C4 179.98(17) . . . . ? C1 N1 C4 C3 -53.8(2) . . . . ? C10 N1 C4 C3 114.2(2) . . . . ? N2 C3 C4 N1 47.9(2) . . . . ? C2 N2 C5 C6 -71.9(2) . . . . ? C3 N2 C5 C6 92.9(2) . . . . ? C11 N3 C6 C5 -115.19(18) . . . . ? C7 N3 C6 C5 118.39(18) . . . . ? N2 C5 C6 N3 -55.4(2) . . . . ? C11 N3 C7 C8 72.8(2) . . . . ? C6 N3 C7 C8 -161.14(17) . . . . ? C18 N4 C8 C7 -160.32(16) . . . . ? C9 N4 C8 C7 78.18(19) . . . . ? N3 C7 C8 N4 73.6(2) . . . . ? C8 N4 C9 C10 -151.10(16) . . . . ? C18 N4 C9 C10 85.3(2) . . . . ? C1 N1 C10 C9 66.1(2) . . . . ? C4 N1 C10 C9 -101.8(2) . . . . ? N4 C9 C10 N1 65.4(2) . . . . ? C7 N3 C11 C12 -171.12(16) . . . . ? C6 N3 C11 C12 62.3(2) . . . . ? N3 C11 C12 C13 -117.8(2) . . . . ? N3 C11 C12 C17 62.5(3) . . . . ? C17 C12 C13 C14 0.8(4) . . . . ? C11 C12 C13 C14 -178.9(2) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C14 C15 C16 C17 0.9(4) . . . . ? C15 C16 C17 C12 0.0(4) . . . . ? C13 C12 C17 C16 -0.8(3) . . . . ? C11 C12 C17 C16 178.9(2) . . . . ? C8 N4 C18 C19 56.6(2) . . . . ? C9 N4 C18 C19 -179.74(19) . . . . ? N4 C18 C19 C20 56.8(3) . . . . ? N4 C18 C19 C24 -124.3(2) . . . . ? C24 C19 C20 C21 1.0(2) . . . . ? C18 C19 C20 C21 179.87(13) . . . . ? C19 C20 C21 C22 -3.06(11) . . . . ? C20 C21 C22 C23 3.6 . . . . ? C21 C22 C23 C24 -2.16(13) . . . . ? C20 C19 C24 C23 0.3(3) . . . . ? C18 C19 C24 C23 -178.59(18) . . . . ? C22 C23 C24 C19 0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.255 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.035 #===END data_ni4a # 1. SUBMISSION DETAILS for compound (Ni4a')(ClO4)2 _publ_contact_author_name # Name of author for correspondance ; Triki Smail ; _publ_contact_author_address # Address of author for correspondance ; UMR CNRS 6521 Universite de Bretagne Occidentale BP 809, Avenue Victor Legorgeu 29285, Brest France ; _publ_contact_author_phone '(33) 298016146' _publ_contact_author_fax '(33) 298016594' _publ_contact_author_email triki@univ-brest.fr # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? # 3. TITLE AND AUTHOR LIST _publ_section_title ; Cis-diprotected cyclam and cyclen : a new route to symmetrically 1,4-disubstituted tetraazamacrocycles and to dissymmetrically tetrasubstituted derivatives. ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address ; Frederic Bellouard, Francoise Chuburu, Nelly Kervarec, Smail Triki, Yves le Mest, Henri Handel ; ; UMR CNRS 6521 Universite de Bretagne Occidentale BP 809, Avenue Victor Legorgeu 29285, Brest France ; 'Loic Toupet ' ; G.M.C.M UMR CNRS 6626 Universite de Rennes Campus de Beaulieu 35042 Rennes cedex France ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. Enraf-Nonius, Cad4-Express Operations Manual, Delft, 1994. Fair, C.K. (1990). MolEN, An Interactive Intelligent System for Crystal Structure Analysis, User Manual, Enraf - Nonius, Delft, The Netherlands. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; data_nicyclamdibenz # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C24H36N4O8Cl2Ni' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24H36N4O8Cl2Ni' _chemical_formula_weight 638.19 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 Cl ? 0.132 0.159 International_Tables_Vol_IV_Table_2.3.1 Ni ? 0.285 1.113 International_Tables_Vol_IV_Table_2.3.1 # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,1/2+y,1/2-z -x,-y,-z +x,1/2-y,1/2+z _cell_length_a 9.785(1) _cell_length_b 27.604(3) _cell_length_c 10.306(1) _cell_angle_alpha 90.00(2) _cell_angle_beta 91.55(2) _cell_angle_gamma 90.00(2) _cell_volume 2782.6(9) _cell_formula_units_z 4 _cell_measurement_temperature 294 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.0 _cell_measurement_theta_max 12.0 _cell_special_details ; ? ; _exptl_crystal_description prism _exptl_crystal_colour 'orange' _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.52 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.945 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 294 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 25 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 4 0 -8 1 -1 -2 3 _diffrn_reflns_number 5312 _diffrn_reflns_av_R_equivalents 0.103 _diffrn_reflns_av_sigmaI/netI 0.667 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 24.97 _reflns_number_total 4761 _reflns_number_gt 1719 _reflns_threshold_expression >1.5\s(I) _computing_data_collection 'CAD4_(Enraf-Nonius,_1994)' _computing_cell_refinement CAD4_(Enraf-Nonius,_1994) _computing_data_reduction 'process_MolEN_(Fair,_1990)' _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_MolEN_(Fair,_1990) _computing_molecular_graphics ? _computing_publication_material BTABLE_PTABLE_CIF_IN_MolEN_(Fair,_1990) # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment refxyz_U=1.3_x_bonding_atom _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1719 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details ; ? ; _refine_ls_R_factor_all 0.246 _refine_ls_R_factor_gt 0.054 _refine_ls_wR_factor_all 0.396 _refine_ls_wR_factor_ref 0.061 _refine_ls_goodness_of_fit_all 8.999 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_shift/su_max 0.526 _refine_ls_shift/esd_mean 0.031 _refine_diff_density_max 0.471 _refine_diff_density_min -0.266 # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol Ni 0.7752(1) 0.11342(4) 0.3644(1) 0.0441(6) Uij ? ? Ni N1 0.7088(7) 0.0639(3) 0.2390(7) 0.051(5) Uij ? ? N N2 0.5875(7) 0.1368(2) 0.3760(7) 0.046(4) Uij ? ? N N3 0.8451(7) 0.1584(3) 0.4949(7) 0.056(5) Uij ? ? N N4 0.9650(7) 0.0960(3) 0.3392(7) 0.053(5) Uij ? ? N C1 0.5643(9) 0.0758(3) 0.2071(9) 0.053(6) Uij ? ? C C2 0.4994(9) 0.0966(3) 0.3260(9) 0.055(6) Uij ? ? C C3 0.5386(9) 0.1473(3) 0.509(1) 0.056(6) Uij ? ? C C4 0.623(1) 0.1842(4) 0.5827(9) 0.066(7) Uij ? ? C C5 0.768(1) 0.1685(4) 0.613(1) 0.074(7) Uij ? ? C C6 0.986(1) 0.1432(4) 0.533(1) 0.074(7) Uij ? ? C C7 1.055(1) 0.1305(4) 0.413(1) 0.078(7) Uij ? ? C C8 1.007(1) 0.0933(4) 0.200(1) 0.067(7) Uij ? ? C C9 0.932(1) 0.0544(4) 0.127(1) 0.069(7) Uij ? ? C C10 0.782(1) 0.0620(3) 0.1117(9) 0.057(6) Uij ? ? C C11 0.7217(9) 0.0160(3) 0.3088(8) 0.049(6) Uij ? ? C C12 0.6809(9) -0.0294(3) 0.2393(8) 0.048(5) Uij ? ? C C13 0.779(1) -0.0611(4) 0.197(1) 0.075(8) Uij ? ? C C14 0.743(1) -0.1053(4) 0.143(1) 0.107(9) Uij ? ? C C15 0.608(1) -0.1187(4) 0.135(1) 0.077(7) Uij ? ? C C16 0.512(1) -0.0876(4) 0.172(1) 0.073(7) Uij ? ? C C17 0.5481(9) -0.0442(3) 0.224(1) 0.061(6) Uij ? ? C C18 0.5745(9) 0.1810(3) 0.2910(9) 0.055(6) Uij ? ? C C19 0.4354(8) 0.2018(3) 0.2684(9) 0.049(5) Uij ? ? C C20 0.384(1) 0.2378(4) 0.344(1) 0.081(7) Uij ? ? C C21 0.253(1) 0.2553(4) 0.321(1) 0.095(8) Uij ? ? C C22 0.173(1) 0.2383(4) 0.221(1) 0.073(7) Uij ? ? C C23 0.222(1) 0.2028(4) 0.148(1) 0.072(7) Uij ? ? C C24 0.352(1) 0.1845(4) 0.169(1) 0.070(7) Uij ? ? C Cl1 0.8347(2) 0.30199(9) 0.4677(2) 0.056(1) Uij ? ? Cl O1 0.6982(7) 0.3149(4) 0.4446(9) 0.114(6) Uij ? ? O O2 0.8558(8) 0.2945(3) 0.6030(7) 0.101(6) Uij ? ? O O3 0.9205(7) 0.3393(3) 0.4244(7) 0.093(5) Uij ? ? O O4 0.8598(9) 0.2595(3) 0.3985(8) 0.098(6) Uij ? ? O Cl2 1.1948(2) -0.01766(9) 0.3352(2) 0.061(1) Uij ? ? Cl O5 1.2520(9) 0.0263(3) 0.360(1) 0.131(7) Uij ? ? O O6 1.2732(7) -0.0531(2) 0.4012(6) 0.075(5) Uij ? ? O O7 1.1894(9) -0.0267(4) 0.2060(7) 0.134(7) Uij ? ? O O8 1.0630(7) -0.0161(3) 0.3827(8) 0.100(6) Uij ? ? O H1 0.5182 0.0475 0.1783 0.0701 Uiso calc C1 H H2 0.5620 0.0994 0.1389 0.0701 Uiso calc C1 H H3 0.4106 0.1077 0.3051 0.0713 Uiso calc C2 H H4 0.4941 0.0716 0.3909 0.0713 Uiso calc C2 H H5 0.5405 0.1177 0.5573 0.0721 Uiso calc C3 H H6 0.4469 0.1585 0.5016 0.0721 Uiso calc C3 H H7 0.5794 0.1907 0.6619 0.0870 Uiso calc C4 H H8 0.6246 0.2129 0.5316 0.0870 Uiso calc C4 H H9 0.8130 0.1938 0.6594 0.0966 Uiso calc C5 H H10 0.7663 0.1401 0.6638 0.0966 Uiso calc C5 H H11 0.9819 0.1160 0.5892 0.1016 Uiso calc C6 H H12 1.0315 0.1691 0.5768 0.1016 Uiso calc C6 H H13 1.0715 0.1589 0.3627 0.1068 Uiso calc C7 H H14 1.1413 0.1154 0.4333 0.1068 Uiso calc C7 H H15 1.1020 0.0863 0.2005 0.0879 Uiso calc C8 H H16 0.9895 0.1235 0.1606 0.0879 Uiso calc C8 H H17 0.9479 0.0247 0.1689 0.0905 Uiso calc C9 H H18 0.9697 0.0535 0.0418 0.0905 Uiso calc C9 H H19 0.7669 0.0921 0.0673 0.0779 Uiso calc C10 H H20 0.7453 0.0365 0.0604 0.0779 Uiso calc C10 H H21 0.6682 0.0181 0.3835 0.0642 Uiso calc C11 H H22 0.8157 0.0124 0.3340 0.0642 Uiso calc C11 H H23 0.8743 -0.0520 0.2044 0.1001 Uiso calc C13 H H24 0.8094 -0.1275 0.1149 0.1372 Uiso calc C14 H H25 0.5811 -0.1486 0.0972 0.1007 Uiso calc C15 H H26 0.4173 -0.0956 0.1595 0.0902 Uiso calc C16 H H27 0.4786 -0.0231 0.2551 0.0813 Uiso calc C17 H H28 0.6099 0.1722 0.2091 0.0714 Uiso calc C18 H H29 0.6301 0.2053 0.3298 0.0714 Uiso calc C18 H H30 0.4399 0.2505 0.4149 0.1067 Uiso calc C20 H H31 0.2183 0.2795 0.3776 0.1183 Uiso calc C21 H H32 0.0855 0.2519 0.2059 0.0943 Uiso calc C22 H H33 0.1638 0.1905 0.0788 0.0939 Uiso calc C23 H H34 0.3830 0.1587 0.1150 0.0888 Uiso calc C24 H H35 0.8492 0.1868 0.4414 0.0742 Uiso calc N3 H H36 0.9704 0.0651 0.3777 0.0702 Uiso calc N4 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol Ni 0.0453(6) 0.0370(6) 0.0513(6) 0.0018(7) -0.0013(5) 0.0020(7) Ni N1 0.050(4) 0.052(5) 0.050(5) 0.002(4) -0.004(4) 0.002(4) N N2 0.052(4) 0.042(4) 0.046(4) 0.002(4) 0.004(4) -0.008(4) N N3 0.059(5) 0.052(5) 0.056(5) -0.004(4) -0.005(4) -0.003(4) N N4 0.054(5) 0.041(4) 0.067(5) 0.010(4) 0.008(4) 0.002(4) N C1 0.060(6) 0.042(6) 0.059(6) 0.003(5) -0.013(5) -0.001(5) C C2 0.059(6) 0.042(6) 0.067(6) 0.006(5) 0.006(5) 0.016(5) C C3 0.061(6) 0.046(6) 0.064(6) 0.008(5) 0.002(5) 0.002(5) C C4 0.092(7) 0.066(7) 0.048(6) 0.009(6) 0.021(6) -0.009(6) C C5 0.092(8) 0.079(7) 0.055(6) -0.006(7) -0.014(6) -0.013(6) C C6 0.062(6) 0.068(7) 0.096(8) -0.007(6) -0.024(6) -0.014(7) C C7 0.064(6) 0.060(7) 0.12(1) -0.027(5) -0.015(7) -0.007(7) C C8 0.050(6) 0.068(7) 0.088(8) 0.015(5) 0.015(6) 0.019(6) C C9 0.072(6) 0.082(8) 0.055(6) 0.009(6) 0.015(5) 0.008(6) C C10 0.077(7) 0.054(6) 0.046(6) 0.011(5) -0.003(5) -0.001(5) C C11 0.062(6) 0.042(5) 0.046(5) 0.006(5) 0.000(5) 0.004(5) C C12 0.059(6) 0.044(5) 0.042(5) 0.007(5) -0.000(5) -0.003(5) C C13 0.056(6) 0.056(7) 0.14(1) -0.005(6) -0.002(7) -0.009(7) C C14 0.096(8) 0.074(7) 0.17(1) -0.002(7) 0.048(7) -0.065(8) C C15 0.102(8) 0.060(6) 0.074(7) -0.028(6) 0.020(6) -0.032(6) C C16 0.079(7) 0.073(7) 0.067(7) -0.007(6) -0.012(6) -0.003(7) C C17 0.048(6) 0.057(7) 0.084(7) 0.000(5) 0.013(5) -0.002(6) C C18 0.067(6) 0.052(6) 0.048(6) 0.016(5) 0.009(5) -0.001(5) C C19 0.047(5) 0.046(6) 0.053(6) 0.002(5) 0.005(5) 0.007(5) C C20 0.078(7) 0.068(7) 0.100(8) 0.026(6) -0.025(6) -0.036(6) C C21 0.095(7) 0.078(7) 0.116(9) 0.051(6) 0.003(7) -0.041(7) C C22 0.080(7) 0.061(7) 0.081(7) 0.014(6) -0.007(6) 0.010(6) C C23 0.075(6) 0.073(7) 0.068(7) 0.006(7) -0.017(6) -0.001(7) C C24 0.071(7) 0.088(8) 0.053(6) 0.027(6) 0.007(5) 0.002(6) C Cl1 0.064(1) 0.050(1) 0.055(1) -0.003(1) -0.005(1) -0.001(1) Cl O1 0.067(5) 0.167(8) 0.132(7) 0.018(5) -0.016(5) 0.032(7) O O2 0.103(6) 0.152(8) 0.066(5) -0.022(6) -0.018(4) 0.019(5) O O3 0.115(5) 0.085(5) 0.081(5) -0.050(4) 0.008(5) 0.007(5) O O4 0.180(7) 0.044(4) 0.119(6) -0.007(5) 0.054(6) -0.013(5) O Cl2 0.055(1) 0.065(2) 0.062(1) 0.017(1) 0.005(1) 0.008(1) Cl O5 0.120(7) 0.061(5) 0.31(1) -0.028(5) -0.054(8) 0.043(7) O O6 0.091(5) 0.077(5) 0.061(5) 0.038(4) 0.005(4) 0.006(4) O O7 0.181(7) 0.34(1) 0.040(5) 0.159(7) 0.005(5) 0.017(7) O O8 0.071(5) 0.127(7) 0.110(6) 0.020(5) 0.027(4) 0.021(6) O # 10. MOLECULAR GEOMETRY 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 Ni N1 1.979(7) . . ? Ni N2 1.954(7) . . ? Ni N3 1.942(7) . . ? Ni N4 1.943(7) . . ? N1 C1 1.48(1) . . ? N1 C10 1.51(1) . . ? N1 C11 1.51(1) . . ? N2 C2 1.49(1) . . ? N2 C3 1.49(1) . . ? N2 C18 1.51(1) . . ? N3 C5 1.48(1) . . ? N3 C6 1.48(1) . . ? N4 C7 1.50(1) . . ? N4 C8 1.51(1) . . ? C1 C2 1.51(1) . . ? C3 C4 1.51(1) . . ? C4 C5 1.50(1) . . ? C6 C7 1.47(2) . . ? C8 C9 1.49(1) . . ? C9 C10 1.49(1) . . ? C11 C12 1.49(1) . . ? C12 C13 1.38(1) . . ? C12 C17 1.37(1) . . ? C13 C14 1.38(2) . . ? C14 C15 1.37(2) . . ? C15 C16 1.34(1) . . ? C16 C17 1.36(1) . . ? C18 C19 1.49(1) . . ? C19 C20 1.37(1) . . ? C19 C24 1.38(1) . . ? C20 C21 1.38(1) . . ? C21 C22 1.36(2) . . ? C22 C23 1.33(1) . . ? C23 C24 1.38(1) . . ? Cl1 O1 1.397(8) . . ? Cl1 O2 1.419(8) . . ? Cl1 O3 1.408(8) . . ? Cl1 O4 1.398(8) . . ? Cl2 O5 1.356(9) . . ? Cl2 O6 1.408(7) . . ? Cl2 O7 1.355(8) . . ? Cl2 O8 1.393(8) . . ? 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 ? ? ? ? ? ? #===END