data_1 _audit_creation_method SHELXL-97 _publ_contact_author ; Prof. Ashwini Nangia School of Chemistry Univerisity of Hyderabad Hyderabad 500 046 India ; _publ_contact_author_email 'ansc@uohyd.ernet.in' _publ_contact_author_phone '91 40 23011338' _publ_contact_author_fax '91 40 23011338' loop_ _publ_author_name 'Balakrishna R. Bhogala' 'Peddy Vishweshwar' 'Ashwini Nangia' _journal_name_full '?' _exptl_crystal_preparation Methanol _chemical_name_systematic ; Ammonium cyclohexane-1-carboxylate-3cis,5cis-dicarboxylic acid ; _chemical_melting_point '504' _chemical_formula_moiety '(C9 H11 O6-) (N H4+)' _chemical_formula_sum 'C9 H15 N O6' _chemical_formula_weight 233.22 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc ' 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' _cell_length_a 4.7608(11) _cell_length_b 19.703(5) _cell_length_c 11.502(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.551(4) _cell_angle_gamma 90.00 _cell_volume 1078.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4639 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 28.29 _exptl_crystal_description 'laths' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type 'none' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method 'phi and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_decay_% '1' _diffrn_reflns_number 4639 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.29 _reflns_number_total 2330 _reflns_number_gt 2291 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v5.059 (Bruker, 1999)' _computing_cell_refinement 'Bruker SMART v5.059 (Bruker, 1999)' _computing_data_reduction 'Bruker SAINT v6.02A (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON (Spek, 1992)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.1480P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(7) _refine_ls_number_reflns 2330 _refine_ls_number_parameters 205 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O14 O 0.3052(2) 0.04742(5) 0.75618(9) 0.0147(2) Uani 1 1 d . . . O15 O 0.1088(2) 0.11430(5) 0.88795(9) 0.0178(2) Uani 1 1 d . . . O10 O 0.1811(2) 0.33556(5) 0.58427(9) 0.0169(2) Uani 1 1 d . . . C5 C -0.0858(3) 0.07915(7) 0.58529(12) 0.0109(3) Uani 1 1 d . . . O13 O -0.4819(2) 0.01805(6) 0.42557(9) 0.0192(2) Uani 1 1 d . . . O11 O 0.2969(2) 0.28311(6) 0.41966(10) 0.0194(2) Uani 1 1 d . . . O12 O -0.2329(2) 0.07153(6) 0.28940(10) 0.0182(2) Uani 1 1 d . . . C8 C -0.3131(2) 0.06670(7) 0.38890(12) 0.0115(3) Uani 1 1 d . . . C3 C -0.0682(3) 0.17703(7) 0.44475(13) 0.0118(3) Uani 1 1 d . . . C4 C -0.2392(3) 0.11611(7) 0.48584(12) 0.0102(2) Uani 1 1 d . . . C7 C 0.1576(3) 0.28771(7) 0.51712(12) 0.0115(3) Uani 1 1 d . . . C6 C -0.0413(3) 0.12668(6) 0.68889(12) 0.0101(2) Uani 1 1 d . . . C2 C -0.0251(3) 0.22671(7) 0.54592(12) 0.0109(2) Uani 1 1 d . . . C1 C 0.1096(3) 0.19268(7) 0.65364(12) 0.0111(2) Uani 1 1 d . . . C9 C 0.1340(3) 0.09308(7) 0.78503(12) 0.0114(2) Uani 1 1 d . . . N16 N -0.2785(3) 0.42305(6) 0.62512(11) 0.0142(2) Uani 1 1 d . . . H5B H 0.098(4) 0.0628(10) 0.5525(18) 0.014(4) Uiso 1 1 d . . . H3B H 0.114(5) 0.1619(10) 0.4181(18) 0.016(5) Uiso 1 1 d . . . H3A H -0.155(4) 0.1984(10) 0.3800(19) 0.013(4) Uiso 1 1 d . . . H1B H 0.111(4) 0.2241(9) 0.7191(17) 0.009(4) Uiso 1 1 d . . . H6 H -0.231(4) 0.1359(10) 0.7276(19) 0.016(5) Uiso 1 1 d . . . H4 H -0.401(4) 0.1315(10) 0.5209(17) 0.012(4) Uiso 1 1 d . . . H2 H -0.206(5) 0.2439(13) 0.574(2) 0.025(5) Uiso 1 1 d . . . H13 H -0.529(8) -0.0021(17) 0.363(3) 0.061(9) Uiso 1 1 d . . . H1A H 0.313(5) 0.1804(11) 0.6368(19) 0.021(5) Uiso 1 1 d . . . H5A H -0.188(4) 0.0418(10) 0.6105(18) 0.013(5) Uiso 1 1 d . . . H16D H -0.230(6) 0.4662(15) 0.658(2) 0.041(7) Uiso 1 1 d . . . H16C H -0.417(5) 0.4097(12) 0.668(2) 0.023(5) Uiso 1 1 d . . . H16B H -0.316(5) 0.4224(13) 0.550(3) 0.030(6) Uiso 1 1 d . . . H16A H -0.126(6) 0.4019(14) 0.638(2) 0.034(6) Uiso 1 1 d . . . H11 H 0.406(7) 0.3177(18) 0.410(3) 0.059(9) 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 O14 0.0181(5) 0.0174(5) 0.0085(5) -0.0016(4) -0.0027(4) 0.0062(4) O15 0.0254(5) 0.0213(5) 0.0067(5) -0.0009(4) -0.0017(4) 0.0095(4) O10 0.0198(5) 0.0157(5) 0.0153(5) -0.0037(4) 0.0020(4) -0.0017(4) C5 0.0139(5) 0.0119(6) 0.0067(6) 0.0008(4) -0.0016(5) -0.0007(4) O13 0.0267(5) 0.0220(5) 0.0089(5) -0.0032(4) 0.0018(4) -0.0125(4) O11 0.0283(6) 0.0181(5) 0.0120(5) -0.0020(4) 0.0050(4) -0.0102(4) O12 0.0225(5) 0.0233(5) 0.0089(5) -0.0013(4) 0.0017(4) -0.0074(4) C8 0.0118(6) 0.0133(6) 0.0092(6) 0.0008(5) -0.0020(5) -0.0004(4) C3 0.0140(6) 0.0140(6) 0.0073(6) 0.0007(5) -0.0012(5) -0.0023(4) C4 0.0109(5) 0.0137(6) 0.0061(6) 0.0003(5) 0.0000(5) 0.0002(4) C7 0.0122(5) 0.0125(6) 0.0098(6) 0.0028(5) -0.0032(5) 0.0010(4) C6 0.0114(5) 0.0128(5) 0.0063(6) 0.0007(5) 0.0002(5) 0.0011(4) C2 0.0128(5) 0.0129(6) 0.0072(6) 0.0006(5) -0.0005(5) -0.0002(4) C1 0.0131(5) 0.0131(6) 0.0070(6) -0.0001(5) -0.0005(5) -0.0004(4) C9 0.0145(5) 0.0122(6) 0.0075(6) 0.0015(5) -0.0006(5) 0.0005(5) N16 0.0172(6) 0.0165(6) 0.0088(6) -0.0013(4) 0.0007(5) 0.0014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O14 C9 1.2605(17) . ? O15 C9 1.2623(18) . ? O10 C7 1.2231(18) . ? C5 C6 1.5289(19) . ? C5 C4 1.5348(19) . ? C5 H5B 1.010(19) . ? C5 H5A 0.93(2) . ? O13 C8 1.3226(16) . ? O13 H13 0.85(4) . ? O11 C7 1.3113(18) . ? O11 H11 0.86(4) . ? O12 C8 1.2136(18) . ? C8 C4 1.5190(18) . ? C3 C4 1.5275(18) . ? C3 C2 1.5329(18) . ? C3 H3B 0.97(2) . ? C3 H3A 0.95(2) . ? C4 H4 0.92(2) . ? C7 C2 1.5220(18) . ? C6 C9 1.5296(18) . ? C6 C1 1.5417(18) . ? C6 H6 1.03(2) . ? C2 C1 1.5431(18) . ? C2 H2 0.98(2) . ? C1 H1B 0.97(2) . ? C1 H1A 1.02(2) . ? N16 H16D 0.96(3) . ? N16 H16C 0.87(3) . ? N16 H16B 0.88(3) . ? N16 H16A 0.85(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C5 C4 110.58(11) . . ? C6 C5 H5B 111.8(12) . . ? C4 C5 H5B 106.4(12) . . ? C6 C5 H5A 108.1(12) . . ? C4 C5 H5A 111.2(13) . . ? H5B C5 H5A 108.8(16) . . ? C8 O13 H13 103(2) . . ? C7 O11 H11 112(2) . . ? O12 C8 O13 123.72(13) . . ? O12 C8 C4 124.69(12) . . ? O13 C8 C4 111.57(11) . . ? C4 C3 C2 109.55(11) . . ? C4 C3 H3B 109.7(12) . . ? C2 C3 H3B 108.8(13) . . ? C4 C3 H3A 111.2(12) . . ? C2 C3 H3A 111.5(12) . . ? H3B C3 H3A 106.0(17) . . ? C8 C4 C3 113.38(11) . . ? C8 C4 C5 110.38(11) . . ? C3 C4 C5 110.64(11) . . ? C8 C4 H4 110.0(12) . . ? C3 C4 H4 109.0(12) . . ? C5 C4 H4 102.9(12) . . ? O10 C7 O11 123.30(12) . . ? O10 C7 C2 121.35(13) . . ? O11 C7 C2 115.24(12) . . ? C5 C6 C9 111.65(11) . . ? C5 C6 C1 111.92(11) . . ? C9 C6 C1 107.63(10) . . ? C5 C6 H6 109.2(12) . . ? C9 C6 H6 103.8(12) . . ? C1 C6 H6 112.3(12) . . ? C7 C2 C3 114.31(11) . . ? C7 C2 C1 106.49(11) . . ? C3 C2 C1 112.56(11) . . ? C7 C2 H2 107.7(14) . . ? C3 C2 H2 111.2(14) . . ? C1 C2 H2 103.9(13) . . ? C6 C1 C2 112.73(11) . . ? C6 C1 H1B 109.5(11) . . ? C2 C1 H1B 110.1(11) . . ? C6 C1 H1A 107.2(13) . . ? C2 C1 H1A 109.9(13) . . ? H1B C1 H1A 107.3(16) . . ? O14 C9 O15 123.42(13) . . ? O14 C9 C6 117.92(12) . . ? O15 C9 C6 118.58(12) . . ? H16D N16 H16C 103(2) . . ? H16D N16 H16B 117(2) . . ? H16C N16 H16B 114(2) . . ? H16D N16 H16A 99(2) . . ? H16C N16 H16A 114(2) . . ? H16B N16 H16A 109(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.353 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.048