#------------------------------------------------------------------------------ #$Date: 2012-03-31 01:21:36 +0300 (Sat, 31 Mar 2012) $ #$Revision: 50154 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/50/4505087.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4505087 loop_ _publ_author_name 'Bhogala, Balakrishna R.' 'Vishweshwar, Peddy' 'Nangia, Ashwini' _publ_contact_author ; Prof. Ashwini Nangia School of Chemistry Univerisity of Hyderabad Hyderabad 500 046 India ; _publ_section_title ; Equivalence of NH4+, NH2NH3+, and OHNH3+in Directing the Noncentrosymmetric Diamondoid Network of O−H···O-Hydrogen Bonds in Dihydrogen Cyclohexane Tricarboxylate ; _journal_issue 3 _journal_name_full 'Crystal Growth & Design' _journal_page_first 1271 _journal_volume 5 _journal_year 2005 _chemical_formula_moiety '(C9 H11 O6-) (N2 H5+)' _chemical_formula_sum 'C9 H16 N2 O6' _chemical_formula_weight 248.24 _chemical_melting_point 468 _chemical_name_systematic ; Hydrazinium Cyclohexane-3cis,5cis-dicarboxylic acid-1-carboxylate ; _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.361(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.4329(14) _cell_length_b 17.829(5) _cell_length_c 11.820(3) _cell_measurement_reflns_used 717 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 26.39 _cell_measurement_theta_min 3.93 _cell_volume 1141.6(5) _computing_cell_refinement 'Bruker SAINT+ (Bruker, 1999a)' _computing_data_collection 'Bruker SMART-NT (Bruker, 1998)' _computing_data_reduction 'Bruker XPREP (Bruker, 1999a)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 3831 _diffrn_reflns_theta_full 28.00 _diffrn_reflns_theta_max 28.00 _diffrn_reflns_theta_min 2.28 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS:Sheldrick, 1996' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.444 _exptl_crystal_description plate _exptl_crystal_F_000 528 _exptl_crystal_preparation Methanol _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.214 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.050 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2245 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.002 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0414 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0828 _refine_ls_wR_factor_ref 0.0896 _reflns_number_gt 1813 _reflns_number_total 2245 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file cg0500270si20050125_084033.cif _[local]_cod_data_source_block 3 _[local]_cod_cif_authors_sg_H-M 'C c' _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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 4505087 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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags N2 N 0.1123(5) 0.36142(14) 0.1870(2) 0.0304(5) Uani 1 1 d . N1 N 0.0196(5) 0.41740(13) 0.2616(2) 0.0276(5) Uani 1 1 d . O5 O 0.3079(3) 0.02781(10) 0.44103(15) 0.0280(5) Uani 1 1 d . O4 O -0.4645(3) 0.03789(10) 0.11319(15) 0.0286(5) Uani 1 1 d . O1 O -0.5581(3) 0.27273(10) 0.44621(15) 0.0250(4) Uani 1 1 d . O2 O -0.4157(3) 0.36022(9) 0.33425(16) 0.0287(5) Uani 1 1 d . C3 C -0.1903(4) 0.13379(12) 0.18819(19) 0.0155(5) Uani 1 1 d . H3 H -0.0460 0.1572 0.1578 0.019 Uiso 1 1 calc R O3 O -0.3396(3) 0.12154(10) -0.00724(14) 0.0265(5) Uani 1 1 d . C5 C 0.0301(4) 0.12481(12) 0.3830(2) 0.0168(5) Uani 1 1 d . H5A H 0.1656 0.1528 0.3525 0.020 Uiso 1 1 calc R C4 C -0.0997(5) 0.08078(13) 0.2845(2) 0.0196(5) Uani 1 1 d . H4A H -0.2389 0.0537 0.3111 0.024 Uiso 1 1 calc R H4B H 0.0138 0.0445 0.2564 0.024 Uiso 1 1 calc R O6 O 0.0926(4) 0.07849(12) 0.57472(16) 0.0353(5) Uani 1 1 d . C9 C 0.1418(4) 0.07478(14) 0.4758(2) 0.0200(5) Uani 1 1 d . C1 C -0.2307(4) 0.23756(13) 0.3344(2) 0.0177(5) Uani 1 1 d . H1A H -0.0842 0.2633 0.3102 0.021 Uiso 1 1 calc R C7 C -0.4072(4) 0.29628(13) 0.37247(19) 0.0194(5) Uani 1 1 d . C6 C -0.1465(5) 0.18208(13) 0.4277(2) 0.0176(5) Uani 1 1 d . H6A H -0.0647 0.2089 0.4913 0.021 Uiso 1 1 calc R H6B H -0.2889 0.1565 0.4542 0.021 Uiso 1 1 calc R C2 C -0.3547(4) 0.19612(14) 0.2312(2) 0.0178(5) Uani 1 1 d . H2A H -0.5088 0.1743 0.2518 0.021 Uiso 1 1 calc R H2B H -0.3931 0.2318 0.1705 0.021 Uiso 1 1 calc R C8 C -0.3389(4) 0.09393(13) 0.0911(2) 0.0181(5) Uani 1 1 d . H2C H 0.001(7) 0.3607(19) 0.127(4) 0.062(12) Uiso 1 1 d . H1C H 0.013(6) 0.4698(18) 0.231(3) 0.046(9) Uiso 1 1 d . H5 H 0.378(7) 0.002(2) 0.502(3) 0.051(10) Uiso 1 1 d . H2D H 0.252(7) 0.3836(19) 0.173(3) 0.053(10) Uiso 1 1 d . H1 H -0.662(8) 0.323(2) 0.468(3) 0.089(13) Uiso 1 1 d . H1B H -0.132(7) 0.404(2) 0.275(3) 0.053(11) Uiso 1 1 d . H1D H 0.111(7) 0.420(2) 0.320(4) 0.055(11) Uiso 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N2 0.0273(13) 0.0361(14) 0.0282(14) 0.0036(11) 0.0036(11) -0.0004(11) N1 0.0401(15) 0.0244(13) 0.0172(12) 0.0036(10) -0.0051(11) -0.0091(11) O5 0.0349(10) 0.0329(11) 0.0157(10) 0.0015(8) -0.0009(8) 0.0176(9) O4 0.0412(11) 0.0246(10) 0.0187(10) 0.0060(7) -0.0076(8) -0.0184(9) O1 0.0306(10) 0.0208(9) 0.0249(10) 0.0025(8) 0.0107(8) 0.0066(8) O2 0.0379(12) 0.0186(10) 0.0302(10) 0.0059(8) 0.0064(9) 0.0057(8) C3 0.0200(12) 0.0159(11) 0.0109(11) 0.0004(9) 0.0028(9) -0.0024(10) O3 0.0375(11) 0.0298(10) 0.0117(9) 0.0041(8) -0.0019(8) -0.0140(8) C5 0.0174(11) 0.0167(12) 0.0162(11) 0.0002(10) 0.0012(9) -0.0006(10) C4 0.0244(12) 0.0192(12) 0.0147(11) 0.0005(10) -0.0021(9) 0.0017(10) O6 0.0434(12) 0.0480(12) 0.0147(10) 0.0049(9) 0.0039(8) 0.0220(10) C9 0.0195(12) 0.0234(13) 0.0165(13) -0.0047(10) -0.0024(10) 0.0009(11) C1 0.0208(12) 0.0157(12) 0.0165(12) -0.0017(9) 0.0012(10) -0.0009(10) C7 0.0220(12) 0.0173(13) 0.0184(13) -0.0012(10) -0.0030(10) -0.0006(10) C6 0.0203(12) 0.0194(12) 0.0128(12) -0.0014(9) -0.0008(9) 0.0004(10) C2 0.0190(12) 0.0194(12) 0.0148(11) 0.0006(9) -0.0002(9) -0.0001(10) C8 0.0189(12) 0.0181(12) 0.0169(13) -0.0005(10) -0.0003(10) 0.0008(10) 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 N1 N2 H2C 104(2) N1 N2 H2D 98(2) H2C N2 H2D 113(3) N2 N1 H1C 115.2(19) N2 N1 H1B 107(2) H1C N1 H1B 108(3) N2 N1 H1D 109(3) H1C N1 H1D 105(3) H1B N1 H1D 112(4) C9 O5 H5 109(2) C7 O1 H1 105(2) C8 C3 C4 113.14(18) C8 C3 C2 107.32(18) C4 C3 C2 111.24(19) C8 C3 H3 108.3 C4 C3 H3 108.3 C2 C3 H3 108.3 C9 C5 C6 111.96(19) C9 C5 C4 112.79(18) C6 C5 C4 110.0(2) C9 C5 H5A 107.3 C6 C5 H5A 107.3 C4 C5 H5A 107.3 C5 C4 C3 110.62(18) C5 C4 H4A 109.5 C3 C4 H4A 109.5 C5 C4 H4B 109.5 C3 C4 H4B 109.5 H4A C4 H4B 108.1 O6 C9 O5 122.5(2) O6 C9 C5 124.1(2) O5 C9 C5 113.3(2) C7 C1 C6 113.36(19) C7 C1 C2 108.61(19) C6 C1 C2 110.56(19) C7 C1 H1A 108.1 C6 C1 H1A 108.1 C2 C1 H1A 108.1 O2 C7 O1 122.4(2) O2 C7 C1 122.8(2) O1 C7 C1 114.8(2) C5 C6 C1 110.25(19) C5 C6 H6A 109.6 C1 C6 H6A 109.6 C5 C6 H6B 109.6 C1 C6 H6B 109.6 H6A C6 H6B 108.1 C3 C2 C1 112.29(19) C3 C2 H2A 109.1 C1 C2 H2A 109.1 C3 C2 H2B 109.1 C1 C2 H2B 109.1 H2A C2 H2B 107.9 O4 C8 O3 122.8(2) O4 C8 C3 118.8(2) O3 C8 C3 118.3(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N2 N1 1.448(3) N2 H2C 0.89(4) N2 H2D 0.88(4) N1 H1C 1.00(3) N1 H1B 0.88(4) N1 H1D 0.82(4) O5 C9 1.320(3) O5 H5 0.91(4) O4 C8 1.249(3) O1 C7 1.310(3) O1 H1 1.09(5) O2 C7 1.226(3) C3 C8 1.528(3) C3 C4 1.531(3) C3 C2 1.537(3) C3 H3 0.9800 O3 C8 1.262(3) C5 C9 1.506(3) C5 C6 1.523(3) C5 C4 1.531(3) C5 H5A 0.9800 C4 H4A 0.9700 C4 H4B 0.9700 O6 C9 1.221(3) C1 C7 1.511(3) C1 C6 1.525(3) C1 C2 1.537(3) C1 H1A 0.9800 C6 H6A 0.9700 C6 H6B 0.9700 C2 H2A 0.9700 C2 H2B 0.9700 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 C9 C5 C4 C3 -175.1(2) C6 C5 C4 C3 59.1(3) C8 C3 C4 C5 -175.6(2) C2 C3 C4 C5 -54.7(3) C6 C5 C9 O6 1.6(3) C4 C5 C9 O6 -123.1(3) C6 C5 C9 O5 -175.8(2) C4 C5 C9 O5 59.5(3) C6 C1 C7 O2 148.2(2) C2 C1 C7 O2 -88.5(3) C6 C1 C7 O1 -34.5(3) C2 C1 C7 O1 88.8(2) C9 C5 C6 C1 173.03(19) C4 C5 C6 C1 -60.8(2) C7 C1 C6 C5 179.9(2) C2 C1 C6 C5 57.7(3) C8 C3 C2 C1 176.6(2) C4 C3 C2 C1 52.3(2) C7 C1 C2 C3 -178.7(2) C6 C1 C2 C3 -53.7(3) C4 C3 C8 O4 31.4(3) C2 C3 C8 O4 -91.7(2) C4 C3 C8 O3 -152.4(2) C2 C3 C8 O3 84.6(3)