#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/07/2200751.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_2200751 loop_ _publ_author_name 'Gilardi, Richard D.' 'Axenrod, Theodore' 'Sun, Jianguang' 'Flippen-Anderson, Judith L.' _publ_section_title ; 5,5-Dihydroxy-1,3-dipropionyl-1,3-diazacyclohexane ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1183 _journal_page_last o1184 _journal_paper_doi 10.1107/S1600536801019006 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C10 H18 N2 O4' _chemical_formula_moiety 'C10 H18 N2 O4' _chemical_formula_sum 'C10 H18 N2 O4' _chemical_formula_weight 230.26 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 118.0230(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 24.2121(16) _cell_length_b 5.3063(4) _cell_length_c 19.7644(12) _cell_measurement_reflns_used 3629 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 28.1 _cell_measurement_theta_min 2.7 _cell_volume 2241.6(3) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_structure_refinement 'SHELXTL (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Bruker SMART 1000' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0407 _diffrn_reflns_av_sigmaI/netI .0369 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 6438 _diffrn_reflns_theta_full 25.28 _diffrn_reflns_theta_max 25.28 _diffrn_reflns_theta_min 1.91 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .105 _exptl_absorpt_correction_T_max .984 _exptl_absorpt_correction_T_min .961 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(Bruker, 2001)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'thick plate' _exptl_crystal_F_000 992 _exptl_crystal_size_max .11 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .40 _refine_diff_density_max .198 _refine_diff_density_min -.178 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.237 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2044 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.237 _refine_ls_R_factor_all .0884 _refine_ls_R_factor_gt .0656 _refine_ls_shift/su_max .003 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0406P)^2^+2.4823P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1346 _reflns_number_gt 1621 _reflns_number_total 2044 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6067.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2200751 _cod_database_fobs_code 2200751 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 N1 .11545(9) .1981(4) .11352(11) .0345(5) Uani d . 1 . . N C1 .12767(11) .0227(5) .07321(14) .0343(6) Uani d . 1 . . C O1 .08695(9) -.0438(4) .00922(11) .0561(6) Uani d . 1 . . O C1A .19260(12) -.0856(5) .10688(14) .0396(7) Uani d . 1 . . C H1AA .2223 .0503 .1170 .048 Uiso calc R 1 . . H H1AB .2025 -.1653 .1554 .048 Uiso calc R 1 . . H C1B .20001(15) -.2757(6) .05528(17) .0594(9) Uani d . 1 . . C H1BA .2425 -.3347 .0787 .089 Uiso calc R 1 . . H H1BB .1899 -.1984 .0069 .089 Uiso calc R 1 . . H H1BC .1724 -.4152 .0472 .089 Uiso calc R 1 . . H C2 .15803(11) .2790(5) .19165(14) .0359(6) Uani d . 1 . . C H2A .1983 .1977 .2089 .043 Uiso calc R 1 . . H H2B .1642 .4598 .1925 .043 Uiso calc R 1 . . H N3 .13260(9) .2143(4) .24266(11) .0327(5) Uani d . 1 . . N C3 .15226(11) -.0008(5) .28538(13) .0340(6) Uani d . 1 . . C O3 .19408(9) -.1287(4) .28501(11) .0495(5) Uani d . 1 . . O C3A .12253(12) -.0661(5) .33506(15) .0411(7) Uani d . 1 . . C H3AA .0798 -.1200 .3026 .049 Uiso calc R 1 . . H H3AB .1211 .0840 .3622 .049 Uiso calc R 1 . . H C3B .15687(14) -.2715(6) .39274(17) .0523(8) Uani d . 1 . . C H3BA .1346 -.3110 .4208 .078 Uiso calc R 1 . . H H3BB .1983 -.2147 .4276 .078 Uiso calc R 1 . . H H3BC .1595 -.4194 .3664 .078 Uiso calc R 1 . . H C4 .07162(11) .3322(5) .21959(14) .0374(6) Uani d . 1 . . C H4A .0758 .5142 .2208 .045 Uiso calc R 1 . . H H4B .0560 .2843 .2549 .045 Uiso calc R 1 . . H C5 .02631(12) .2463(5) .13916(15) .0400(7) Uani d . 1 . . C O5A .01854(10) -.0171(4) .14378(12) .0497(6) Uani d . 1 . . O H5A -.0089(15) -.087(7) .104(2) .070(12) Uiso d . 1 . . H O5B -.02987(9) .3789(5) .11659(12) .0548(6) Uani d . 1 . . O C6 .05270(12) .3048(6) .08438(15) .0432(7) Uani d . 1 . . C H6A .0255 .2345 .0343 .052 Uiso calc R 1 . . H H6B .0544 .4858 .0789 .052 Uiso calc R 1 . . H H5B -.0567(19) .302(7) .072(2) .092(13) Uiso d . 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 N1 .0278(11) .0452(13) .0270(11) .0008(10) .0099(9) .0007(10) C1 .0329(14) .0412(16) .0294(14) -.0036(12) .0150(12) .0018(12) O1 .0365(11) .0818(16) .0365(11) .0009(11) .0059(9) -.0196(11) C1A .0333(15) .0489(17) .0330(14) .0007(13) .0126(12) .0010(13) C1B .061(2) .069(2) .0457(18) .0226(18) .0226(15) .0014(16) C2 .0314(14) .0408(16) .0318(13) -.0062(12) .0118(11) -.0059(12) N3 .0276(11) .0403(13) .0285(11) .0001(10) .0118(9) -.0050(10) C3 .0281(13) .0409(16) .0268(13) .0000(12) .0078(11) -.0066(12) O3 .0478(12) .0546(13) .0505(12) .0163(10) .0268(10) .0070(10) C3A .0401(15) .0450(17) .0372(15) -.0022(13) .0174(12) -.0046(13) C3B .0571(19) .053(2) .0461(17) -.0030(16) .0239(15) .0081(15) C4 .0373(15) .0380(16) .0350(14) .0034(12) .0155(12) -.0045(12) C5 .0319(14) .0470(19) .0363(15) .0075(13) .0120(12) -.0022(13) O5A .0435(12) .0511(14) .0492(13) -.0052(10) .0173(11) -.0092(11) O5B .0352(11) .0792(16) .0426(12) .0202(11) .0121(10) -.0069(11) C6 .0341(14) .0555(18) .0331(14) .0069(13) .0101(12) .0003(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C1 N1 C2 125.9(2) C1 N1 C6 120.8(2) C2 N1 C6 112.9(2) O1 C1 N1 120.8(2) O1 C1 C1A 120.6(2) N1 C1 C1A 118.5(2) C1B C1A C1 112.9(2) C1B C1A H1AA 109.0 C1 C1A H1AA 109.0 C1B C1A H1AB 109.0 C1 C1A H1AB 109.0 H1AA C1A H1AB 107.8 C1A C1B H1BA 109.5 C1A C1B H1BB 109.5 H1BA C1B H1BB 109.5 C1A C1B H1BC 109.5 H1BA C1B H1BC 109.5 H1BB C1B H1BC 109.5 N3 C2 N1 110.28(19) N3 C2 H2A 109.6 N1 C2 H2A 109.6 N3 C2 H2B 109.6 N1 C2 H2B 109.6 H2A C2 H2B 108.1 C3 N3 C2 119.3(2) C3 N3 C4 123.8(2) C2 N3 C4 112.2(2) O3 C3 N3 120.6(2) O3 C3 C3A 121.8(2) N3 C3 C3A 117.5(2) C3 C3A C3B 113.3(2) C3 C3A H3AA 108.9 C3B C3A H3AA 108.9 C3 C3A H3AB 108.9 C3B C3A H3AB 108.9 H3AA C3A H3AB 107.7 C3A C3B H3BA 109.5 C3A C3B H3BB 109.5 H3BA C3B H3BB 109.5 C3A C3B H3BC 109.5 H3BA C3B H3BC 109.5 H3BB C3B H3BC 109.5 N3 C4 C5 108.9(2) N3 C4 H4A 109.9 C5 C4 H4A 109.9 N3 C4 H4B 109.9 C5 C4 H4B 109.9 H4A C4 H4B 108.3 O5B C5 O5A 112.1(2) O5B C5 C4 107.3(2) O5A C5 C4 106.3(2) O5B C5 C6 109.8(2) O5A C5 C6 111.0(2) C4 C5 C6 110.2(2) C5 O5A H5A 117(2) C5 O5B H5B 103(2) N1 C6 C5 110.2(2) N1 C6 H6A 109.6 C5 C6 H6A 109.6 N1 C6 H6B 109.6 C5 C6 H6B 109.6 H6A C6 H6B 108.1 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 N1 C1 . 1.345(3) ? N1 C2 . 1.461(3) ? N1 C6 . 1.462(3) ? C1 O1 . 1.235(3) ? C1 C1A . 1.504(4) ? C1A C1B . 1.504(4) ? C1A H1AA . .9700 ? C1A H1AB . .9700 ? C1B H1BA . .9600 ? C1B H1BB . .9600 ? C1B H1BC . .9600 ? C2 N3 . 1.448(3) ? C2 H2A . .9700 ? C2 H2B . .9700 ? N3 C3 . 1.366(3) ? N3 C4 . 1.465(3) ? C3 O3 . 1.222(3) ? C3 C3A . 1.506(3) ? C3A C3B . 1.513(4) ? C3A H3AA . .9700 ? C3A H3AB . .9700 ? C3B H3BA . .9600 ? C3B H3BB . .9600 ? C3B H3BC . .9600 ? C4 C5 . 1.517(4) ? C4 H4A . .9700 ? C4 H4B . .9700 ? C5 O5B . 1.405(3) ? C5 O5A . 1.419(3) ? C5 C6 . 1.525(4) ? O5A H5A . .84(3) ? O5B H5B . .92(4) ? C6 H6A . .9700 ? C6 H6B . .9700 ? 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 O5A H5A O1 5 .84(3) 2.26(3) 2.918(3) 136(3) O5B H5B O1 5 .92(4) 1.97(4) 2.833(3) 157(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132592 2 PubChem 71350828