#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/66/2006671.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_2006671 loop_ _publ_author_name 'Gauthier, Ted J.' 'Yokum, T. Scott' 'Morales, Guillermo A.' 'McLaughlin, Mark L.' 'Liu, Yen-Hsiang' 'Fronczek, Frank R.' _publ_section_title ; Two Cyclohexanespiro-5'-hydantoin Monohydrates ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1659 _journal_page_last 1661 _journal_paper_doi 10.1107/S0108270197007488 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C8 H12 N2 O2, H2O' _chemical_formula_sum 'C8 H14 N2 O3' _chemical_formula_weight 186.21 _chemical_name_systematic ; cyclohexanespiro-5'-hydantoin monohydrate ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.8890(10) _cell_length_b 9.2407(5) _cell_length_c 6.2644(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 30 _cell_measurement_theta_min 14 _cell_volume 977.66(12) _computing_cell_refinement CAD4_Software _computing_data_collection CAD4_Software_(Enraf-Nonius,_1977) _computing_data_reduction PROCESS_MolEN_(Fair,_1990) _computing_molecular_graphics ORTEPII_(Johnson,_1976) _computing_publication_material CIF_IN_MolEN _computing_structure_refinement LSFM_MolEN _computing_structure_solution direct_methods_SHELXS86_(Sheldrick,_1990) _diffrn_measurement_device Enraf_Nonius_CAD4 _diffrn_measurement_method \w/2\q _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 3174 _diffrn_reflns_theta_max 75.0 _diffrn_standards_decay_% 0.4 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.78 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_type \y_scans_(North,_Phillips_&_Mathews,_1968) _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description fragment _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.23 _refine_diff_density_min -0.30 _refine_ls_abs_structure_details ; Refinement of the antipodal structure was inconclusive. For the reported absolute structure, R=0.03803, wR=0.03908, S=1.466, while the alternate structure yielded R=0.03801, wR=0.03910, S=1.467. ; _refine_ls_extinction_coef 8.5(2)\\times10^-6^ _refine_ls_extinction_method isotropic_(Zachariasen,_1963) _refine_ls_goodness_of_fit_obs 1.466 _refine_ls_hydrogen_treatment refall _refine_ls_number_parameters 174 _refine_ls_number_reflns 1722 _refine_ls_R_factor_obs .038 _refine_ls_shift/esd_max 0.005 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .039 _reflns_number_observed 1722 _reflns_number_total 2002 _reflns_observed_criterion >1.0\s(I) _cod_data_source_file fg1332.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 977.6(2) _cod_database_code 2006671 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, 1/2+z' '1/2+x, 1/2-y, z' '1/2-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 O1 .0380(6) .1210(10) .0443(6) .0120(8) .0018(5) .0046(8) O2 .0584(7) .1120(10) .0277(5) .0080(8) -.0008(5) .0013(7) N1' .0381(6) .0760(10) .0239(5) .0060(8) -.0016(5) .0016(7) N3' .0396(7) .0770(10) .0313(6) .0059(8) -.0075(6) .0006(8) C2' .0372(7) .0700(10) .0332(7) .0050(9) -.0024(6) .0030(9) C2 .0541(9) .0510(10) .0513(9) -.0033(9) -.0030(9) .0085(9) C3 .0590(10) .0630(10) .0590(10) -.0180(10) -.0126(9) .0000(10) C4 .0439(9) .084(2) .0680(10) -.0050(10) -.0163(8) .0110(10) C4' .0433(8) .0620(10) .0283(6) .0058(9) -.0032(6) .0007(8) C5 .0451(9) .0600(10) .0580(10) .0101(9) -.0125(8) .0070(10) C5' .0356(7) .0501(8) .0264(6) .0026(8) -.0021(6) .0004(8) C6 .0459(8) .0530(10) .0469(9) .0049(9) -.0058(8) -.0036(9) O1W .0478(6) .0870(10) .0454(6) .0074(8) -.0114(5) -.0034(8) 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 O1 .40878(7) .5878(2) 0 .0679(4) Uani ? O2 .23740(8) .6069(2) .5584(2) .0662(4) Uani ? N1' .27283(7) .6010(2) .0126(2) .0460(4) Uani ? N3' .33847(8) .5985(2) .3146(2) .0494(4) Uani ? C2' .34549(9) .5956(2) .0924(3) .0469(4) Uani ? C2 .15820(10) .4710(2) .1689(3) .0521(5) Uani ? C3 .10360(10) .4736(2) -.0260(4) .0602(6) Uani ? C4 .05520(10) .6101(3) -.0342(4) .0653(6) Uani ? C4' .26220(10) .6043(2) .3754(3) .0446(4) Uani ? C5 .10780(10) .7428(2) -.0300(3) .0541(5) Uani ? C5' .21116(9) .6048(2) .1759(3) .0373(4) Uani ? C6 .16170(10) .7430(2) .1652(3) .0485(4) Uani ? O1W .46711(7) .61340(10) -.4146(2) .0599(4) Uani ? H1N' .2610(10) .600(2) -.114(3) .075(7) Uiso ? H3N' .3810(10) .601(2) .413(3) .082(7) Uiso ? H2a .1270(10) .474(2) .308(4) .062(6) Uiso ? H2b .1950(10) .386(2) .181(4) .077(6) Uiso ? H3a .0690(10) .394(2) -.026(4) .069(6) Uiso ? H3b .1380(10) .466(2) -.151(3) .063(6) Uiso ? H4a .0190(10) .609(2) .107(5) .119(9) Uiso ? H4b .0170(10) .616(2) -.159(4) .091(7) Uiso ? H5a .0730(10) .829(2) -.041(4) .077(7) Uiso ? H5b .1470(10) .744(2) -.161(3) .083(7) Uiso ? H6a .2000(10) .829(2) .165(4) .067(6) Uiso ? H6b .1298(9) .740(2) .304(3) .054(5) Uiso ? H1W .5050(10) .552(2) -.437(5) .110(8) Uiso ? H2W .4460(10) .602(2) -.273(4) .093(8) Uiso ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2' N1' C5' 113.40(10) yes C2' N1' H1N' 125.0(10) no C5' N1' H1N' 120.0(10) no C2' N3' C4' 111.40(10) yes C2' N3' H3N' 125.0(10) no C4' N3' H3N' 122.0(10) no O1 C2' N1' 129.4(2) yes O1 C2' N3' 123.30(10) yes N1' C2' N3' 107.30(10) yes C3 C2 C5' 111.3(2) no C3 C2 H2a 111.0(10) no C3 C2 H2b 116.0(10) no C5' C2 H2a 104.0(10) no C5' C2 H2b 105.0(10) no H2a C2 H2b 106.0(10) no C2 C3 C4 111.6(2) no C2 C3 H3a 111.0(10) no C2 C3 H3b 106.0(10) no C4 C3 H3a 108.0(10) no C4 C3 H3b 110.0(10) no H3a C3 H3b 108.0(10) no C3 C4 C5 111.1(2) no C3 C4 H4a 105.0(10) no C3 C4 H4b 114.0(10) no C5 C4 H4a 108.0(10) no C5 C4 H4b 109.0(10) no H4a C4 H4b 106.0(10) no O2 C4' N3' 126.6(2) yes O2 C4' C5' 125.30(10) yes N3' C4' C5' 108.10(10) yes C4 C5 C6 111.4(2) no C4 C5 H5a 107.0(10) no C4 C5 H5b 111.0(10) no C6 C5 H5a 114.0(10) no C6 C5 H5b 104.0(10) no H5a C5 H5b 108.0(10) no N1' C5' C2 112.20(10) no N1' C5' C4' 99.90(10) yes N1' C5' C6 112.30(10) no C2 C5' C4' 110.70(10) no C2 C5' C6 110.80(10) no C4' C5' C6 110.50(10) no C5 C6 C5' 111.2(2) no C5 C6 H6a 112.0(10) no C5 C6 H6b 111.6(9) no C5' C6 H6a 107.0(10) no C5' C6 H6b 103.0(10) no H6a C6 H6b 110.0(10) no H1W O1W H2W 110(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2' 1.218(2) yes O2 C4' 1.220(2) yes N1' C2' 1.326(2) yes N1' C5' 1.461(2) yes N1' H1N' .82(2) no N3' C2' 1.397(2) yes N3' C4' 1.345(2) yes N3' H3N' .95(2) no C2 C3 1.530(3) no C2 C5' 1.526(2) no C2 H2a 1.02(2) no C2 H2b 1.00(2) no C3 C4 1.505(3) no C3 H3a .94(2) no C3 H3b .98(2) no C4 C5 1.515(3) no C4 H4a 1.07(3) no C4 H4b 1.02(2) no C4' C5' 1.518(2) yes C5 C6 1.525(3) no C5 H5a .99(2) no C5 H5b 1.06(2) no C5' C6 1.528(2) no C6 H6a 1.03(2) no C6 H6b 1.03(2) no O1W H1W .88(2) no O1W H2W .96(2) 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' H1' O2 1_554 0.82(2) 2.09(2) 2.908(2) 176(2) yes N3' H3' O1W 1_556 0.95(2) 1.82(2) 2.760(2) 175(2) yes O1W H2W O1 . 0.96(2) 1.83(2) 2.788(2) 177(2) yes O1W H1W O1 2_664 0.88(2) 1.98(2) 2.852(2) 178(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139055753