#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202417.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_2202417 loop_ _publ_author_name 'Jones, Matthew D.' 'Almeida Paz, Filipe A.' 'Davies, John E.' 'Johnson, Brian F. G.' _publ_section_title ; (R)-(+)-2,2'-Diamino-1,1'-binaphthyl ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o910 _journal_page_last o912 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C20 H16 N2' _chemical_formula_moiety 'C20 H16 N2' _chemical_formula_sum 'C20 H16 N2' _chemical_formula_weight 284.35 _chemical_name_systematic ; (R)-(+)-2,2'-Diamino-1,1'-binaphthalene ; _space_group_IT_number 96 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall 'P 4nw 2abw' _symmetry_space_group_name_H-M 'P 43 21 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.0388(2) _cell_length_b 7.0388(2) _cell_length_c 30.0684(8) _cell_measurement_reflns_used 4522 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.00 _cell_volume 1489.73(7) _computing_cell_refinement 'HKL SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction ; HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK ; _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXTL (Bruker 2001)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin-slice \w and \f' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_number 4236 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 3.54 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_correction_T_min 0.944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.171 _refine_diff_density_min -0.186 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 108 _refine_ls_number_reflns 1061 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0365 _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^)+(0.0563P)^2^+0.37P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0952 _refine_ls_wR_factor_ref 0.0999 _reflns_number_gt 1455 _reflns_number_total 1635 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6256.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal' 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 'Tetragonal' changed to 'tetragonal' 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 2202417 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' 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 N1 0.4707(3) 0.1703(2) -0.05183(5) 0.0366(4) Uani d D 1 . . N H1A 0.368(2) 0.239(3) -0.0574(8) 0.053(7) Uiso d D 1 . . H H1B 0.457(4) 0.0482(16) -0.0579(8) 0.067(8) Uiso d D 1 . . H C1 0.5529(2) 0.2117(2) -0.01137(5) 0.0257(4) Uani d . 1 . . C C2 0.6753(3) 0.0735(2) 0.00785(6) 0.0319(4) Uani d . 1 . . C H2 0.6970 -0.0427 -0.0074 0.038 Uiso calc R 1 . . H C3 0.7617(2) 0.1046(3) 0.04747(6) 0.0303(4) Uani d . 1 . . C H3 0.8408 0.0090 0.0599 0.036 Uiso calc R 1 . . H C4 0.7352(2) 0.2782(2) 0.07047(5) 0.0239(4) Uani d . 1 . . C C5 0.8226(2) 0.3122(3) 0.11225(6) 0.0291(4) Uani d . 1 . . C H5 0.8995 0.2163 0.1253 0.035 Uiso calc R 1 . . H C6 0.7980(3) 0.4804(3) 0.13397(6) 0.0335(4) Uani d . 1 . . C H6 0.8563 0.5006 0.1621 0.040 Uiso calc R 1 . . H C7 0.6859(3) 0.6244(3) 0.11468(6) 0.0328(4) Uani d . 1 . . C H7 0.6703 0.7421 0.1297 0.039 Uiso calc R 1 . . H C8 0.5989(2) 0.5963(2) 0.07429(5) 0.0260(4) Uani d . 1 . . C H8 0.5244 0.6952 0.0617 0.031 Uiso calc R 1 . . H C9 0.6186(2) 0.4215(2) 0.05104(5) 0.0210(3) Uani d . 1 . . C C10 0.5244(2) 0.3859(2) 0.00963(5) 0.0212(3) Uani d . 1 . . C 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 N1 0.0516(11) 0.0268(8) 0.0314(8) 0.0000(8) -0.0124(8) -0.0075(7) C1 0.0293(9) 0.0236(8) 0.0243(8) -0.0021(7) -0.0017(7) 0.0004(6) C2 0.0396(10) 0.0226(8) 0.0335(8) 0.0059(8) 0.0008(8) -0.0021(7) C3 0.0290(9) 0.0280(9) 0.0339(9) 0.0064(7) -0.0016(8) 0.0076(8) C4 0.0194(7) 0.0292(8) 0.0231(8) -0.0022(6) 0.0005(6) 0.0066(7) C5 0.0221(8) 0.0402(9) 0.0248(8) -0.0036(8) -0.0024(7) 0.0101(7) C6 0.0311(9) 0.0475(11) 0.0218(8) -0.0093(9) -0.0052(7) 0.0026(8) C7 0.0377(10) 0.0344(9) 0.0264(8) -0.0074(8) -0.0003(8) -0.0066(8) C8 0.0278(8) 0.0257(8) 0.0245(8) -0.0020(7) -0.0001(7) 0.0002(7) C9 0.0193(7) 0.0238(8) 0.0198(7) -0.0035(6) 0.0015(6) 0.0033(6) C10 0.0218(7) 0.0219(8) 0.0200(7) -0.0011(6) 0.0003(6) 0.0028(6) 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 N1 C1 . 1.378(2) yes N1 H1A . 0.884(10) no N1 H1B . 0.884(10) no C1 C10 . 1.393(2) yes C1 C2 . 1.423(2) yes C2 C3 . 1.355(2) yes C2 H2 . 0.950 no C3 C4 . 1.417(2) yes C3 H3 . 0.950 no C4 C5 . 1.419(2) yes C4 C9 . 1.426(2) yes C5 C6 . 1.363(3) yes C5 H5 . 0.950 no C6 C7 . 1.409(3) yes C6 H6 . 0.950 no C7 C8 . 1.374(2) yes C7 H7 . 0.950 no C8 C9 . 1.422(2) yes C8 H8 . 0.950 no C9 C10 . 1.433(2) yes C10 C10 7 1.496(3) yes 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 H1A . 113.1(15) no C1 N1 H1B . 115.7(16) no H1A N1 H1B . 114(2) no N1 C1 C10 . 121.72(15) yes N1 C1 C2 . 117.93(15) yes C10 C1 C2 . 120.30(15) yes C3 C2 C1 . 121.25(16) yes C3 C2 H2 . 119.4 no C1 C2 H2 . 119.4 no C2 C3 C4 . 120.61(16) yes C2 C3 H3 . 119.7 no C4 C3 H3 . 119.7 no C3 C4 C5 . 121.36(16) yes C3 C4 C9 . 119.09(15) yes C5 C4 C9 . 119.55(16) yes C6 C5 C4 . 121.02(16) yes C6 C5 H5 . 119.5 no C4 C5 H5 . 119.5 no C5 C6 C7 . 119.91(16) yes C5 C6 H6 . 120.0 no C7 C6 H6 . 120.0 no C8 C7 C6 . 120.63(17) yes C8 C7 H7 . 119.7 no C6 C7 H7 . 119.7 no C7 C8 C9 . 121.05(17) yes C7 C8 H8 . 119.5 no C9 C8 H8 . 119.5 no C8 C9 C4 . 117.82(14) yes C8 C9 C10 . 122.26(14) yes C4 C9 C10 . 119.91(15) yes C1 C10 C9 . 118.79(14) yes C1 C10 C10 7 119.46(14) yes C9 C10 C10 7 121.58(15) 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 N1 C1 C2 C3 . 179.76(17) no C10 C1 C2 C3 . 2.3(3) no C1 C2 C3 C4 . -1.3(3) no C2 C3 C4 C5 . 179.19(17) no C2 C3 C4 C9 . -1.0(2) no C3 C4 C5 C6 . 179.34(16) no C9 C4 C5 C6 . -0.5(2) no C4 C5 C6 C7 . -0.7(3) no C5 C6 C7 C8 . 0.8(3) no C6 C7 C8 C9 . 0.3(3) no C7 C8 C9 C4 . -1.5(2) no C7 C8 C9 C10 . 177.85(15) no C3 C4 C9 C8 . -178.28(14) no C5 C4 C9 C8 . 1.6(2) no C3 C4 C9 C10 . 2.4(2) no C5 C4 C9 C10 . -177.80(14) no N1 C1 C10 C9 . -178.22(15) no C2 C1 C10 C9 . -0.8(2) no N1 C1 C10 C10 7 6.4(2) no C2 C1 C10 C10 7 -176.20(14) no C8 C9 C10 C1 . 179.22(14) no C4 C9 C10 C1 . -1.5(2) no C8 C9 C10 C10 7 -5.5(2) no C4 C9 C10 C10 7 173.83(12) no