#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012616.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_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_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_ _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_bond_atom_site_label_1 _geom_bond_atom_site_label_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_ _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