#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202478.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_2202478 loop_ _publ_author_name 'Gilardi, Richard' 'Evans, Robin N.' _publ_section_title ; 2,3,5,6-Tetrahydroxy-1,4-dinitrocyclohexane dihydrate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1226 _journal_page_last o1227 _journal_paper_doi 10.1107/S1600536803016532 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C6 H10 N2 O8, 2H2 O' _chemical_formula_moiety 'C6 H10 N2 O8, 2H2 O' _chemical_formula_sum 'C6 H14 N2 O10' _chemical_formula_weight 274.19 _chemical_name_systematic ; 2,3,5,6-tetrahydroxy-1,4-dinitrocyclohexane dihydrate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 65.180(2) _cell_angle_beta 86.143(2) _cell_angle_gamma 85.995(2) _cell_formula_units_Z 1 _cell_length_a 4.7309(5) _cell_length_b 7.8835(9) _cell_length_c 8.0592(9) _cell_measurement_reflns_used 1494 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 28.206 _cell_measurement_theta_min 2.485 _cell_volume 271.91(5) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 93(2) _diffrn_measured_fraction_theta_full 0.959 _diffrn_measured_fraction_theta_max 0.959 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _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 0.71073 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2086 _diffrn_reflns_theta_full 28.22 _diffrn_reflns_theta_max 28.22 _diffrn_reflns_theta_min 2.79 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_T_max 0.980519 _exptl_absorpt_correction_T_min 0.829895 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SABABS; Bruker, 2001)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 144 _exptl_crystal_size_max .60 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .08 _refine_diff_density_max 0.467 _refine_diff_density_min -0.232 _refine_ls_extinction_coef 0 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 94 _refine_ls_number_reflns 1288 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.092 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0427 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.061P)^2^+0.05P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1028 _refine_ls_wR_factor_ref 0.1078 _reflns_number_gt 1075 _reflns_number_total 1288 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6245.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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 2202478 _cod_database_fobs_code 2202478 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 C1 0.4621(3) 0.0855(2) 0.1334(2) 0.0119(3) Uani d . 1 . . C H1A 0.5494 0.1282 0.2181 0.014 Uiso calc R 1 . . H O1 0.1624(2) 0.10772(17) 0.14720(16) 0.0148(3) Uani d . 1 . . O H1H 0.121(4) 0.207(3) 0.167(3) 0.022 Uiso d . 1 . . H C2 0.5768(3) 0.1966(2) -0.0627(2) 0.0120(3) Uani d . 1 . . C H2A 0.7887 0.1840 -0.0666 0.014 Uiso calc R 1 . . H O2 0.4895(2) 0.38755(16) -0.11657(16) 0.0153(3) Uani d . 1 . . O H2H 0.626(5) 0.450(3) -0.146(3) 0.023 Uiso d . 1 . . H C3 0.4625(3) 0.1227(2) -0.1897(2) 0.0125(3) Uani d . 1 . . C H3A 0.2514 0.1426 -0.1903 0.015 Uiso calc R 1 . . H N3 0.5841(3) 0.22559(19) -0.38254(18) 0.0143(3) Uani d . 1 . . N O3A 0.8056(2) 0.30722(17) -0.40633(16) 0.0203(3) Uani d . 1 . . O O3B 0.4568(2) 0.21747(18) -0.50704(16) 0.0217(3) Uani d . 1 . . O O1W 0.0215(2) 0.41843(17) 0.21501(18) 0.0149(3) Uani d . 1 . . O H1W -0.128(5) 0.476(3) 0.172(3) 0.022 Uiso d . 1 . . H H2W -0.015(4) 0.391(3) 0.324(3) 0.022 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 C1 0.0107(6) 0.0133(7) 0.0137(8) -0.0024(5) 0.0010(5) -0.0075(6) O1 0.0109(5) 0.0159(6) 0.0200(6) -0.0010(4) 0.0025(4) -0.0102(5) C2 0.0108(6) 0.0111(7) 0.0150(8) -0.0022(5) 0.0020(5) -0.0064(6) O2 0.0140(5) 0.0105(6) 0.0208(6) -0.0028(4) 0.0020(4) -0.0061(5) C3 0.0123(6) 0.0140(8) 0.0101(7) -0.0019(6) 0.0021(5) -0.0042(6) N3 0.0159(6) 0.0142(7) 0.0127(7) -0.0004(5) 0.0002(5) -0.0058(6) O3A 0.0190(6) 0.0237(7) 0.0175(6) -0.0095(5) 0.0049(4) -0.0075(5) O3B 0.0243(6) 0.0276(7) 0.0139(6) -0.0036(5) -0.0017(5) -0.0087(5) O1W 0.0141(5) 0.0158(6) 0.0144(6) -0.0002(4) 0.0013(4) -0.0064(5) 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_1 _geom_angle_site_symmetry_3 _geom_angle O1 C1 C3 . 2_655 107.68(11) O1 C1 C2 . . 111.37(12) C3 C1 C2 2_655 . 109.11(11) O1 C1 H1A . . 109.6 C3 C1 H1A 2_655 . 109.6 C2 C1 H1A . . 109.6 C1 O1 H1H . . 108.3(14) O2 C2 C3 . . 110.27(12) O2 C2 C1 . . 108.29(11) C3 C2 C1 . . 109.83(12) O2 C2 H2A . . 109.5 C3 C2 H2A . . 109.5 C1 C2 H2A . . 109.5 C2 O2 H2H . . 109.5(15) N3 C3 C2 . . 110.44(12) N3 C3 C1 . 2_655 106.86(11) C2 C3 C1 . 2_655 112.84(12) N3 C3 H3A . . 108.9 C2 C3 H3A . . 108.9 C1 C3 H3A 2_655 . 108.9 O3A N3 O3B . . 123.73(13) O3A N3 C3 . . 119.12(12) O3B N3 C3 . . 117.12(12) H1W O1W H2W . . 99.4(19) 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 C1 O1 . 1.4192(17) ? C1 C3 2_655 1.530(2) ? C1 C2 . 1.532(2) ? C1 H1A . 1.00 ? O1 H1H . 0.87(2) ? C2 O2 . 1.4188(18) ? C2 C3 . 1.517(2) ? C2 H2A . 1.00 ? O2 H2H . 0.80(2) ? C3 N3 . 1.5136(19) ? C3 C1 2_655 1.530(2) ? C3 H3A . 1.00 ? N3 O3A . 1.2300(17) ? N3 O3B . 1.2303(18) ? O1W H1W . 0.83(2) ? O1W H2W . 0.82(2) ? 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 O1 H1H O1W . 0.87(2) 1.89(2) 2.7549(16) 178(2) O2 H2H O1W 2_665 0.80(2) 1.95(2) 2.7478(16) 175(2) O1W H1W O2 2_565 0.83(2) 1.93(2) 2.7450(16) 169(2) O1W H2W O3A 1_456 0.82(2) 2.12(2) 2.9299(17) 168(2) loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion O1 C1 C2 O2 . . 57.59(15) C3 C1 C2 O2 2_655 . 176.31(11) O1 C1 C2 C3 . . -62.89(15) C3 C1 C2 C3 2_655 . 55.83(16) O2 C2 C3 N3 . . 63.18(14) C1 C2 C3 N3 . . -177.56(11) O2 C2 C3 C1 . 2_655 -177.30(11) C1 C2 C3 C1 . 2_655 -58.03(15) C2 C3 N3 O3A . . 21.12(18) C1 C3 N3 O3A 2_655 . -101.96(15) C2 C3 N3 O3B . . -160.94(12) C1 C3 N3 O3B 2_655 . 75.98(15) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139066051