#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/26/2012616.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_2012616 loop_ _publ_author_name 'Mashuta, Mark S.' 'Pimenov, Konstantin V.' 'Grapperhaus, Craig A.' _publ_section_title ; cis-Dioxocyclam ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o226 _journal_page_last o227 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C10 H20 N4 O2' _chemical_formula_sum 'C10 H20 N4 O2' _chemical_formula_weight 228.30 _chemical_name_common cis-Dioxocyclam _chemical_name_systematic ; 1,4,8,11-Tetraazacyclotetradecane-5,7-dione ; _space_group_IT_number 64 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-C 2ac 2' _symmetry_space_group_name_H-M 'C m c a' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.1714(9) _cell_length_b 9.0190(5) _cell_length_c 17.2111(10) _cell_measurement_reflns_used 7156 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.26 _cell_measurement_theta_min 2.37 _cell_volume 2355.0(2) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.960 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_device_type 'SMART APEX CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_av_sigmaI/netI 0.013 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9566 _diffrn_reflns_theta_full 28.30 _diffrn_reflns_theta_max 28.30 _diffrn_reflns_theta_min 2.37 _diffrn_standards_decay_% <1 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2001)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.28 _exptl_crystal_density_meas 1.23 _exptl_crystal_density_method picnometry _exptl_crystal_description block _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.32 _refine_diff_density_max 0.36 _refine_diff_density_min -0.14 _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.08 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 98 _refine_ls_number_reflns 1455 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.08 _refine_ls_R_factor_all 0.036 _refine_ls_R_factor_gt 0.034 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.044P)^2^+1.24P] where P=(Fo^2^+Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.087 _refine_ls_wR_factor_ref 0.088 _reflns_number_gt 1359 _reflns_number_total 1455 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bk1641.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M Cmca _[local]_cod_cif_authors_sg_Hall '-C 2bc 2' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012616 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' '-x, y+1/2, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' 'x, -y-1/2, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y, -z-1/2' 'x+1/2, -y, z-1/2' '-x+1/2, y+1/2, z' 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.10535(5) 0.21627(7) 0.30402(4) 0.0237(2) Uani d . 1 . . O N1 0.09778(5) 0.63132(8) 0.43791(5) 0.0203(2) Uani d . 1 . . N H1NA 0.0942(13) 0.564(2) 0.4674(12) 0.013(5) Uiso d P 0.50 . . H H1NB 0.0534(14) 0.605(2) 0.4122(12) 0.013(5) Uiso d P 0.50 . . H N2 0.11837(5) 0.46558(8) 0.29273(4) 0.0188(2) Uani d . 1 . . N H2NA 0.1043(8) 0.5433(14) 0.2655(7) 0.029(3) Uiso d . 1 . . H C1 0.17912(5) 0.62745(10) 0.39300(5) 0.0204(2) Uani d . 1 . . C H1A 0.2300 0.6406 0.4284 0.029(3) Uiso calc R 1 . . H H1B 0.1793 0.7106 0.3554 0.024(3) Uiso calc R 1 . . H C2 0.18899(5) 0.48208(10) 0.34940(5) 0.0209(2) Uani d . 1 . . C H2A 0.2467 0.4799 0.3225 0.028(3) Uiso calc R 1 . . H H2B 0.1872 0.3985 0.3866 0.026(3) Uiso calc R 1 . . H C3 0.08071(6) 0.33573(9) 0.27639(5) 0.0181(2) Uani d . 1 . . C C4 0.0000 0.34517(13) 0.22393(7) 0.0198(3) Uani d S 1 . . C H4A 0.0000 0.2625 0.1861 0.029(4) Uiso calc SR 1 . . H H4B 0.0000 0.4399 0.1949 0.023(4) Uiso calc SR 1 . . H C5 0.08458(6) 0.77339(9) 0.47752(5) 0.0207(2) Uani d . 1 . . C H5A 0.0825 0.8539 0.4384 0.022(3) Uiso calc R 1 . . H H5B 0.1352 0.7926 0.5124 0.027(3) Uiso calc R 1 . . H C6 0.0000 0.77510(14) 0.52476(7) 0.0230(3) Uani d S 1 . . C H6A 0.0000 0.6878 0.5596 0.027(4) Uiso calc SR 1 . . H H6B 0.0000 0.8648 0.5579 0.035(5) Uiso calc SR 1 . . 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 O1 0.0351(4) 0.0139(3) 0.0221(3) 0.0037(2) 0.0003(3) 0.0006(2) N1 0.0178(4) 0.0166(4) 0.0265(4) -0.0029(3) 0.0017(3) -0.0031(3) N2 0.0207(4) 0.0141(4) 0.0217(4) 0.0018(3) 0.0012(3) 0.0024(3) C1 0.0150(4) 0.0203(4) 0.0259(4) -0.0032(3) -0.0019(3) 0.0022(3) C2 0.0153(4) 0.0208(4) 0.0265(4) 0.0023(3) 0.0020(3) 0.0025(3) C3 0.0248(4) 0.0155(4) 0.0142(4) 0.0024(3) 0.0061(3) -0.0012(3) C4 0.0318(7) 0.0142(5) 0.0134(5) 0.000 0.000 -0.0019(4) C5 0.0242(4) 0.0171(4) 0.0209(4) -0.0027(3) -0.0059(3) -0.0025(3) C6 0.0340(7) 0.0193(6) 0.0156(5) 0.000 0.000 -0.0044(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C3 . 1.2360(10) yes N1 C1 . 1.4570(10) yes N1 C5 . 1.4650(10) yes N1 H1NA . 0.80(2) yes N1 H1NB . 0.84(2) yes N2 C3 . 1.3330(10) yes N2 C2 . 1.4560(10) yes N2 H2NA . 0.870(10) yes C1 C2 . 1.518(2) no C1 H1A . 0.99 no C1 H1B . 0.99 no C2 H2A . 0.99 no C2 H2B . 0.99 no C3 C4 . 1.5240(10) no C4 H4A . 0.99 no C4 H4B . 0.99 no C5 C6 . 1.5190(10) no C5 H5A . 0.99 no C5 H5B . 0.99 no C6 H6A . 0.99 no C6 H6B . 0.99 no 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C5 . 112.56(7) yes C1 N1 H1NA . 112.2(15) yes C5 N1 H1NA . 111.5(15) yes C1 N1 H1NB . 113.1(13) yes C5 N1 H1NB . 112.5(14) yes H1NA N1 H1NB . 93.6(19) yes C3 N2 C2 . 123.12(7) yes C3 N2 H2NA . 119.3(8) yes C2 N2 H2NA . 117.3(8) yes N1 C1 C2 . 111.50(7) yes N1 C1 H1A . 109.3 no C2 C1 H1A . 109.3 no N1 C1 H1B . 109.3 no C2 C1 H1B . 109.3 no H1A C1 H1B . 108.0 no N2 C2 C1 . 110.29(7) yes N2 C2 H2A . 109.6 no C1 C2 H2A . 109.6 no N2 C2 H2B . 109.6 no C1 C2 H2B . 109.6 no H2A C2 H2B . 108.1 no O1 C3 N2 . 123.72(8) yes O1 C3 C4 . 121.33(8) yes N2 C3 C4 . 114.86(8) yes C3 C4 H4A . 110.3 no C3 C4 H4B . 110.3 no H4A C4 H4B . 108.6 no N1 C5 C6 . 111.92(8) yes N1 C5 H5A . 109.2 no C6 C5 H5A . 109.2 no N1 C5 H5B . 109.2 no C6 C5 H5B . 109.2 no H5A C5 H5B . 107.9 no C5 C6 H6A . 108.5 no C5 C6 H6B . 108.5 no H6A C6 H6B . 107.5 no C3 C4 C3 7_555 106.95(9) no C5 C6 C5 7_555 115.27(9) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1NA N1 4_566 0.80(2) 2.40(2) 3.1900(10) 173.9(15) yes N1 H1NB N1 12 0.84(2) 2.35(2) 2.9670(10) 131.0(14) yes N2 H2NA O1 10_566 0.870(10) 1.97(2) 2.8150(10) 164.9(13) yes _cod_database_fobs_code 2012616 _journal_paper_doi 10.1107/S0108270102003165