#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/06/2000643.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2000643 loop_ _publ_author_name 'Reibenspies, J. H.' _publ_contact_author ; Dr. Joseph H. Reibenspies Department of Chemistry Texas A & M University College Station, Texas 77845 U.S.A. ; _publ_section_title ; Structure of 1,4,7,10-tetraazacyclododecane trihydrate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1717 _journal_page_last 1718 _journal_paper_doi 10.1107/S0108270192006723 _journal_volume 48 _journal_year 1992 _chemical_formula_moiety 'C8 H20 N4, 3(H2 O)' _chemical_formula_sum 'C8 H26 N4 O3' _chemical_formula_weight 226.3 _chemical_name_common cyclen _chemical_name_systematic ; 1,4,7,10-tetrazacyclododecane ; _space_group_IT_number 68 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-C 2a 2ac' _symmetry_space_group_name_H-M 'C c c a :2' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.636(4) _cell_length_b 16.873(3) _cell_length_c 8.881(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 27.53 _cell_measurement_theta_min 9.19 _cell_volume 2492.9(9) _computing_data_collection 'Siemens P3VAX version 3.4' _computing_data_reduction 'REFRED (Reibenspies, 1992)' _computing_publication_material 'SHELXTL-PLUS ' _computing_structure_refinement SHELXTL-PLUS _computing_structure_solution 'SHELXTL-PLUS (Sheldrick, 1990)' _diffrn_ambient_temperature 296 _diffrn_measurement_device 'Siemens R3m/V diffractometer' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_sigmaI/netI 0.04 _diffrn_reflns_number 1273 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 5 _diffrn_standards_interval_time 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.206 _exptl_crystal_description parallelepiped _exptl_crystal_F_000 1008 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _refine_diff_density_max 0.24 _refine_diff_density_min -0.27 _refine_ls_extinction_coef 0.0004(2) _refine_ls_extinction_method 'Larsen (1967)' _refine_ls_goodness_of_fit_all 1.302 _refine_ls_goodness_of_fit_obs 1.452 _refine_ls_matrix_type full _refine_ls_number_constraints 6 _refine_ls_number_parameters 71 _refine_ls_number_reflns 814 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_obs 0.0520 _refine_ls_shift/esd_max 0.0021 _refine_ls_shift/esd_mean 0.0003 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F)+0.0005F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0622 _refine_ls_wR_factor_obs 0.0586 _reflns_number_observed 814 _reflns_number_total 1270 _reflns_observed_criterion refln_observed_if_F_>_2.5_\s(F) _cod_data_source_file st1013.cif _cod_data_source_block cyclen _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(F)+0.0005F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F)+0.0005F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2492.9(8) _cod_original_sg_symbol_Hall '-C 2b 2ac' _cod_original_sg_symbol_H-M 'C c c a' _cod_database_code 2000643 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' 1/2+x, 1/2+y, +z' ' -x, -y, -z' ' 1/2-x, 1/2-y, -z' ' 1/2-x, -y, +z' ' 1-x, 1/2-y, +z' '-1/2+x, +y, -z' ' +x, 1/2+y, -z' ' -x, +y, 1/2-z' ' 1/2-x, 1/2+y, 1/2-z' ' +x, -y, -1/2+z' ' 1/2+x, 1/2-y, -1/2+z' ' 1/2+x, -y, 1/2-z' ' 1+x, 1/2-y, 1/2-z' '-1/2-x, +y, -1/2+z' ' -x, 1/2+y, -1/2+z' 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 O(1) .045(2) .061(2) .043(2) 0 .004(2) 0 O(2) .067(2) .048(2) .060(2) -.016(2) 0 0 O(3) .0350(10) .0410(10) .046(2) 0 0 -.0040(10) N(1) .0390(10) .0360(10) .0320(10) -.0040(10) -.0020(10) -.0010(10) N(2) .0350(10) .0350(10) .0310(10) .0000(10) -.0020(10) -.0010(10) C(1) .0370(10) .0370(10) .0340(10) .0040(10) .0020(10) .0000(10) C(2) .0340(10) .039(2) .044(2) .0010(10) .0040(10) .0010(10) C(3) .037(2) .039(2) .037(2) .0030(10) -.0010(10) .0060(10) C(4) .040(2) .0340(10) .041(2) .0020(10) -.0030(10) .0010(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_refinement_flags O(1) .5000 .2500 -.0269(3) .0490(10) Uani ? ? S O(2) .5000 .1484(2) .2500 .0580(10) Uani ? ? S O(3) .12680(10) .2500 .2500 .0410(10) Uani ? ? S N(1) .37020(10) .02300(10) .1368(2) .0360(10) Uani ? ? . N(2) .22200(10) .12400(10) .1367(2) .0340(10) Uani ? ? . C(1) .3335(2) -.1024(2) .0152(3) .0360(10) Uani ? ? . C(2) .4010(2) -.0513(2) .0753(3) .0390(10) Uani ? ? . C(3) .3534(2) .0826(2) .0211(3) .0380(10) Uani ? ? . C(4) .3014(2) .1491(2) .0840(3) .0380(10) Uani ? ? . H(1O1) .5423 .2474 -.0874 .080 Uiso d ? RT H(1O2) .4848 .1902 .1728 .080 Uiso d ? RT H(1O3) .1640 .2039 .2259 .080 Uiso d ? RT H(1) .4026 .0499 .1996 .080 Uiso d ? RT H(2) .2279 .0799 .1927 .080 Uiso d ? RT H(1A) .3546 -.1500 -.0293 .080 Uiso calc C(1) RT H(1B) .3051 -.0733 -.0613 .080 Uiso calc C(1) RT H(2A) .4277 -.0802 .1540 .080 Uiso calc C(2) RT H(2B) .4396 -.0415 -.0032 .080 Uiso calc C(2) RT H(3A) .3226 .0573 -.0569 .080 Uiso calc C(3) RT H(3B) .4021 .1025 -.0234 .080 Uiso calc C(3) RT H(4A) .3291 .1716 .1688 .080 Uiso calc C(4) RT H(4B) .2950 .1896 .0088 .080 Uiso calc C(4) RT loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.017 0.009 International_Tables_Vol_IV_Table_2.2B H 0 0 International_Tables_Vol_IV_Table_2.2B N 0.029 0.018 International_Tables_Vol_IV_Table_2.2B O 0.047 0.032 International_Tables_Vol_IV_Table_2.2B loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 -2 0 -2 -4 0 -1 -1 -2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H(1O1) O(1) H(1O1) . . 6_555 105.0(10) ? H(1O2) O(2) H(1O2) . . 9_655 92.0(10) ? H(1O3) O(3) H(1O3) . . 14_455 105.0(10) ? H(1) N(1) C(2) . . . 117.0(10) ? H(1) N(1) C(3) . . . 101.0(10) ? C(2) N(1) C(3) . . . 113.2(2) yes H(2) N(2) C(4) . . . 108.0(10) ? H(2) N(2) C(1) . . 5_555 106.0(10) ? C(4) N(2) C(1) . . 5_555 113.9(2) yes H(1A) C(1) H(1B) . . . 108.0(10) ? H(1A) C(1) C(2) . . . 110.0(10) ? H(1B) C(1) C(2) . . . 109.0(10) ? H(1A) C(1) N(2) . . 5_555 109.0(10) ? H(1B) C(1) N(2) . . 5_555 109.0(10) ? C(2) C(1) N(2) . . 5_555 110.5(2) yes N(1) C(2) C(1) . . . 111.1(2) yes N(1) C(2) H(2A) . . . 109.0(10) ? C(1) C(2) H(2A) . . . 108.0(10) ? N(1) C(2) H(2B) . . . 111.0(10) ? C(1) C(2) H(2B) . . . 109.0(10) ? H(2A) C(2) H(2B) . . . 108.0(10) ? N(1) C(3) H(3A) . . . 108.0(10) ? N(1) C(3) H(3B) . . . 112.0(10) ? H(3A) C(3) H(3B) . . . 108.0(10) ? N(1) C(3) C(4) . . . 110.9(2) yes H(3A) C(3) C(4) . . . 107.0(10) ? H(3B) C(3) C(4) . . . 112.0(10) ? N(2) C(4) C(3) . . . 114.7(2) yes N(2) C(4) H(4A) . . . 107.0(10) ? C(3) C(4) H(4A) . . . 109.0(10) ? N(2) C(4) H(4B) . . . 109.0(10) ? C(3) C(4) H(4B) . . . 109.0(10) ? H(4A) C(4) H(4B) . . . 108.0(10) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O(1) H(1O1) . . 0.886 ? O(1) H(1O1) . 6_555 0.886 ? O(2) H(1O2) . . 1.016 ? O(2) H(1O2) . 9_655 1.016 ? O(3) H(1O3) . . 1.017 ? O(3) H(1O3) . 14_455 1.017 ? N(1) H(1) . . 0.900 ? N(1) C(2) . . 1.460(3) yes N(1) C(3) . . 1.465(3) yes N(2) H(2) . . 0.900 ? N(2) C(4) . . 1.464(3) yes N(2) C(1) . 5_555 1.466(3) yes C(1) H(1A) . . 0.961 ? C(1) H(1B) . . 0.961 ? C(1) C(2) . . 1.513(4) yes C(3) C(4) . . 1.523(4) yes C(1) N(2) . 5_555 1.466(3) yes C(2) H(2A) . . 0.961 ? C(2) H(2B) . . 0.962 ? C(3) H(3A) . . 0.962 ? C(3) H(3B) . . 0.962 ? C(4) H(4A) . . 0.961 ? C(4) H(4B) . . 0.961 ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 71345808