#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202539.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_2202539 loop_ _publ_author_name 'Ng, Seik Weng' _publ_section_title ; Bis(diisopropylammonium) 2,6-naphthalenedicarboxylate ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1028 _journal_page_last o1029 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety '2C6 H16 N 1+, C12 H6 O4 2-' _chemical_formula_sum 'C24 H38 N2 O4' _chemical_formula_weight 418.56 _chemical_name_systematic ; Bis(diisopropylammonium) 2,6-naphthalenedicarboxylate ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 67.7490(10) _cell_angle_beta 88.1790(10) _cell_angle_gamma 75.3890(10) _cell_formula_units_Z 1 _cell_length_a 7.8718(7) _cell_length_b 8.5597(7) _cell_length_c 10.1327(9) _cell_measurement_reflns_used 1895 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.3 _cell_measurement_theta_min 2.2 _cell_volume 609.92(9) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2001)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.91 _diffrn_measured_fraction_theta_max 0.91 _diffrn_measurement_device_type 'Bruker AXS area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _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 0.045 _diffrn_reflns_av_sigmaI/netI 0.102 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5309 _diffrn_reflns_theta_full 28.3 _diffrn_reflns_theta_max 28.3 _diffrn_reflns_theta_min 2.2 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type none _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Parallelepiped _exptl_crystal_F_000 228 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.18 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.72 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 144 _refine_ls_number_reflns 2756 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.72 _refine_ls_R_factor_all 0.094 _refine_ls_R_factor_gt 0.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0622P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.134 _refine_ls_wR_factor_ref 0.141 _reflns_number_gt 1084 _reflns_number_total 2756 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cm6049.cif _[local]_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. '_exptl_absorpt_correction_type' value 'None' changed to 'none' 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 2202539 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_type_symbol O1 0.1618(2) 0.7424(2) 0.0754(2) 0.0718(5) Uani d . 1 O O2 0.0445(2) 0.5200(2) 0.1817(2) 0.0703(5) Uani d . 1 O N1 -0.0312(2) 0.7867(2) -0.1596(2) 0.0480(5) Uani d D 1 N C1 0.1489(3) 0.6093(3) 0.1786(3) 0.0522(6) Uani d . 1 C C2 0.2649(2) 0.5541(3) 0.3127(2) 0.0438(5) Uani d . 1 C C3 0.4116(3) 0.6094(3) 0.3098(2) 0.0492(6) Uani d . 1 C C4 0.5243(2) 0.5559(2) 0.4347(2) 0.0430(5) Uani d . 1 C C5 0.2194(3) 0.4437(3) 0.4432(2) 0.0540(6) Uani d . 1 C C6 0.3210(3) 0.3924(3) 0.5664(2) 0.0560(6) Uani d . 1 C C7 0.0867(3) 0.8525(3) -0.2746(2) 0.0557(6) Uani d . 1 C C8 0.1107(4) 1.0249(3) -0.2835(3) 0.0859(9) Uani d . 1 C C9 0.2587(3) 0.7146(3) -0.2438(3) 0.0801(8) Uani d . 1 C C10 -0.2124(3) 0.9000(3) -0.1695(2) 0.0570(6) Uani d . 1 C C11 -0.3107(3) 0.9439(3) -0.3092(3) 0.0828(9) Uani d . 1 C C12 -0.3063(3) 0.8026(4) -0.0440(3) 0.0890(9) Uani d . 1 C H1n1 0.028 0.765 -0.077 0.038(6) Uiso d D 1 H H1n2 -0.038 0.685 -0.155 0.061(7) Uiso d D 1 H H3 0.4400 0.6847 0.2234 0.059 Uiso calc R 1 H H5 0.1186 0.4049 0.4459 0.065 Uiso calc R 1 H H6 0.2866 0.3219 0.6523 0.067 Uiso calc R 1 H H7 0.0326 0.8689 -0.3663 0.067 Uiso calc R 1 H H8a -0.0014 1.1096 -0.3055 0.129 Uiso calc R 1 H H8b 0.1878 1.0639 -0.3572 0.129 Uiso calc R 1 H H8c 0.1611 1.0113 -0.1935 0.129 Uiso calc R 1 H H9a 0.2378 0.6074 -0.2402 0.120 Uiso calc R 1 H H9b 0.3125 0.6961 -0.1535 0.120 Uiso calc R 1 H H9c 0.3357 0.7523 -0.3179 0.120 Uiso calc R 1 H H10 -0.2045 1.0086 -0.1616 0.068 Uiso calc R 1 H H11a -0.2499 1.0069 -0.3867 0.124 Uiso calc R 1 H H11b -0.4274 1.0147 -0.3117 0.124 Uiso calc R 1 H H11c -0.3173 0.8380 -0.3184 0.124 Uiso calc R 1 H H12a -0.2425 0.7780 0.0438 0.134 Uiso calc R 1 H H12b -0.3125 0.6948 -0.0500 0.134 Uiso calc R 1 H H12c -0.4231 0.8732 -0.0466 0.134 Uiso calc R 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 O1 0.0900(10) 0.0700(10) 0.0520(10) -0.0310(10) -0.0210(10) -0.0110(10) O2 0.0770(10) 0.0630(10) 0.0800(10) -0.0230(10) -0.0220(10) -0.0300(10) N1 0.0530(10) 0.0450(10) 0.0460(10) -0.0120(10) -0.0100(10) -0.0170(10) C1 0.0550(10) 0.0500(10) 0.058(2) -0.0080(10) -0.0110(10) -0.0300(10) C2 0.0470(10) 0.0410(10) 0.0470(10) -0.0120(10) -0.0020(10) -0.0200(10) C3 0.0570(10) 0.0440(10) 0.0470(10) -0.0130(10) -0.0020(10) -0.0170(10) C4 0.0440(10) 0.0410(10) 0.0470(10) -0.0120(10) 0.0020(10) -0.0190(10) C5 0.0500(10) 0.061(2) 0.056(2) -0.0210(10) -0.0020(10) -0.0240(10) C6 0.0580(10) 0.061(2) 0.053(2) -0.0280(10) 0.0080(10) -0.0190(10) C7 0.0670(10) 0.0560(10) 0.0480(10) -0.0240(10) 0.0050(10) -0.0190(10) C8 0.107(2) 0.061(2) 0.099(2) -0.042(2) 0.034(2) -0.028(2) C9 0.072(2) 0.075(2) 0.099(2) -0.024(2) 0.026(2) -0.038(2) C10 0.0540(10) 0.0530(10) 0.062(2) -0.0070(10) -0.0080(10) -0.0240(10) C11 0.067(2) 0.083(2) 0.087(2) -0.0010(10) -0.025(2) -0.031(2) C12 0.062(2) 0.116(2) 0.081(2) -0.018(2) 0.014(2) -0.033(2) 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 _geom_angle_publ_flag C7 N1 C10 . . 117.7(2) yes O1 C1 O2 . . 125.4(2) yes O1 C1 C2 . . 117.5(2) yes O2 C1 C2 . . 117.1(2) yes C3 C2 C5 . . 119.2(2) yes C3 C2 C1 . . 121.4(2) yes C5 C2 C1 . . 119.5(2) yes C2 C3 C4 . . 122.1(2) yes C6 C4 C4 2_666 2_666 119.2(2) yes C6 C4 C3 2_666 . 123.1(2) yes C4 C4 C3 2_666 . 117.7(2) yes C6 C5 C2 . . 120.9(2) yes C5 C6 C4 . 2_666 121.0(2) yes N1 C7 C8 . . 110.9(2) yes N1 C7 C9 . . 107.9(2) yes C8 C7 C9 . . 112.2(2) yes N1 C10 C11 . . 111.4(2) yes N1 C10 C12 . . 107.5(2) yes C11 C10 C12 . . 111.0(2) yes C10 N1 H1n1 . . 111 no C7 N1 H1n1 . . 105 no C10 N1 H1n2 . . 109 no C7 N1 H1n2 . . 109 no H1n1 N1 H1n2 . . 105 no C2 C3 H3 . . 119.0 no C4 C3 H3 . . 119.0 no C6 C5 H5 . . 119.6 no C2 C5 H5 . . 119.6 no C5 C6 H6 . . 119.5 no C4 C6 H6 2_666 . 119.5 no N1 C7 H7 . . 108.6 no C8 C7 H7 . . 108.6 no C9 C7 H7 . . 108.6 no C7 C8 H8a . . 109.5 no C7 C8 H8b . . 109.5 no H8a C8 H8b . . 109.5 no C7 C8 H8c . . 109.5 no H8a C8 H8c . . 109.5 no H8b C8 H8c . . 109.5 no C7 C9 H9a . . 109.5 no C7 C9 H9b . . 109.5 no H9a C9 H9b . . 109.5 no C7 C9 H9c . . 109.5 no H9a C9 H9c . . 109.5 no H9b C9 H9c . . 109.5 no N1 C10 H10 . . 109.0 no C11 C10 H10 . . 109.0 no C12 C10 H10 . . 109.0 no C10 C11 H11a . . 109.5 no C10 C11 H11b . . 109.5 no H11a C11 H11b . . 109.5 no C10 C11 H11c . . 109.5 no H11a C11 H11c . . 109.5 no H11b C11 H11c . . 109.5 no C10 C12 H12a . . 109.5 no C10 C12 H12b . . 109.5 no H12a C12 H12b . . 109.5 no C10 C12 H12c . . 109.5 no H12a C12 H12c . . 109.5 no H12b C12 H12c . . 109.5 no 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 O1 C1 . 1.245(3) yes O2 C1 . 1.248(2) yes N1 C7 . 1.495(3) yes N1 C10 . 1.491(3) yes C1 C2 . 1.509(3) yes C2 C3 . 1.349(3) yes C2 C5 . 1.402(3) yes C3 C4 . 1.424(3) yes C4 C6 2_666 1.396(3) yes C4 C4 2_666 1.416(4) yes C5 C6 . 1.364(3) yes C6 C4 2_666 1.396(3) yes C7 C8 . 1.504(3) yes C7 C9 . 1.505(3) yes C10 C11 . 1.505(3) yes C10 C12 . 1.518(3) yes N1 H1n1 . 0.90 no N1 H1n2 . 0.87 no C3 H3 . 0.93 no C5 H5 . 0.93 no C6 H6 . 0.93 no C7 H7 . 0.98 no C8 H8a . 0.96 no C8 H8b . 0.96 no C8 H8c . 0.96 no C9 H9a . 0.96 no C9 H9b . 0.96 no C9 H9c . 0.96 no C10 H10 . 0.98 no C11 H11a . 0.96 no C11 H11b . 0.96 no C11 H11c . 0.96 no C12 H12a . 0.96 no C12 H12b . 0.96 no C12 H12c . 0.96 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 H1n1 O1 . 0.90 1.82 2.716(2) 173 yes N1 H1n2 O2 2_565 0.87 1.88 2.746(2) 169 yes 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_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C3 . -19.8(3) no O2 C1 C2 C3 . 161.9(2) no O1 C1 C2 C5 . 159.9(2) no O2 C1 C2 C5 . -18.4(3) no C5 C2 C3 C4 . 1.5(3) no C1 C2 C3 C4 . -178.8(2) no C2 C3 C4 C6 2_666 178.3(2) no C2 C3 C4 C4 2_666 -1.3(3) no C3 C2 C5 C6 . 0.2(3) no C1 C2 C5 C6 . -179.6(2) no C2 C5 C6 C4 2_666 -1.9(3) no C10 N1 C7 C8 . 58.4(3) no C10 N1 C7 C9 . -178.4(2) no C7 N1 C10 C11 . 56.5(3) no C7 N1 C10 C12 . 178.3(2) no