#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008197.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_2008197 loop_ _publ_author_name 'Lian Ee Khoo' 'Hong Juan Hu' 'Alan Hazell' _publ_section_title ; 4-Chloro-2-[2-(dimethylamino)ethylaminomethyl]phenol and 2-[2-(dimethylamino)ethylaminomethyl]-6-methoxyphenol ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 245 _journal_page_last 248 _journal_paper_doi 10.1107/S0108270198012050 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C12 H20 N2 O2' _chemical_formula_weight 224.310 _chemical_name_systematic ; 2-[2-dimethylamino)ethylaminomethyl]-6-methoxyphenol ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.9034(8) _cell_length_b 10.5054(5) _cell_length_c 16.1559(8) _cell_measurement_reflns_used 7440 _cell_measurement_temperature 298 _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 2.5 _cell_volume 2699.2(2) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction SAINT _computing_molecular_graphics ; ORTEPIII (Burnett & Johnson, 1996) and KRYSTAL ; _computing_publication_material KRYSTAL _computing_structure_refinement 'modified ORFLS (Busing et al., 1962) and KRYSTAL' _computing_structure_solution 'SIR92 (Altomare et al., 1994) and KRYSTAL (Hazell, 1995)' _diffrn_ambient_temperature 298 _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method ; \w rotation scans with narrow frames ; _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 19817 _diffrn_reflns_reduction_process 18470 _diffrn_reflns_theta_max 25.7 _diffrn_reflns_theta_min 2.5 _exptl_absorpt_coefficient_mu 0.0754 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_type 'multi-scan (SADABS; Siemens, 1995)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.34 _refine_diff_density_max 0.17(3) _refine_diff_density_min -0.15(3) _refine_ls_extinction_coef '0.26 (7) x 10^3^' _refine_ls_extinction_method ; B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974) ; _refine_ls_goodness_of_fit_ref 1.569 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 154 _refine_ls_number_reflns 1872 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.048 _refine_ls_shift/esd_max 0.00128 _refine_ls_shift/esd_mean 0.00016 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/{[\s~cs~(F^2^)+1.05F^2^]^1/2^-|F|}^2^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.056 _reflns_number_observed 1795 _reflns_number_total 3558 _reflns_observed_criterion I>3\s(I) _[local]_cod_data_source_file sk1230.cif _[local]_cod_data_source_block 1b _cod_depositor_comments ; The following automatic conversions were performed: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 16 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value ' 1/{[\s~cs~(F^2^)+1.05F^2^]^1/2^-|F|}^2^' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/{[\s~cs~(F^2^)+1.05F^2^]^1/2^-|F|}^2^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2008197 _cod_database_fobs_code 2008197 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,+z +x,1/2-y,1/2+z 1/2+x,+y,1/2-z 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 0.0580(10) 0.0430(10) 0.1100(10) -0.0010(10) -0.0100(10) 0.0070(10) O2 0.0790(10) 0.0480(10) 0.212(2) -0.0110(10) -0.0130(10) 0.0240(10) N1 0.0590(10) 0.0410(10) 0.0670(10) 0.0030(10) 0.0040(10) 0.0050(10) N2 0.0750(10) 0.114(2) 0.0670(10) -0.0120(10) -0.0060(10) 0.0050(10) C1 0.0570(10) 0.0470(10) 0.0640(10) -0.0010(10) -0.0040(10) -0.0070(10) C2 0.0650(10) 0.0500(10) 0.103(2) -0.0040(10) -0.0030(10) -0.0080(10) C3 0.0660(10) 0.0690(10) 0.134(2) -0.0120(10) -0.0040(10) -0.0200(10) C4 0.0600(10) 0.093(2) 0.130(2) 0.0040(10) -0.0180(10) -0.024(2) C5 0.0750(10) 0.0730(10) 0.0810(10) 0.0160(10) -0.0150(10) -0.0120(10) C6 0.0660(10) 0.0520(10) 0.0510(10) 0.0060(10) -0.0020(10) -0.0070(10) C7 0.0800(10) 0.0520(10) 0.0570(10) 0.0080(10) 0.0060(10) 0.0080(10) C8 0.0620(10) 0.0530(10) 0.0770(10) 0.0060(10) 0.0020(10) -0.0070(10) C9 0.0730(10) 0.083(2) 0.0830(10) -0.0100(10) 0.0070(10) -0.0250(10) C10 0.152(3) 0.148(3) 0.117(2) -0.046(2) -0.009(2) 0.048(2) C11 0.120(3) 0.241(5) 0.102(2) -0.032(3) -0.033(2) -0.003(2) C12 0.126(2) 0.067(2) 0.217(4) -0.023(2) -0.001(2) 0.032(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_thermal_displace_type O1 0.27700(10) 0.33640(10) 0.12000(10) 0.0700(10) Uani O2 0.36990(10) 0.54720(10) 0.10000(10) 0.1130(10) Uani N1 0.31450(10) 0.04860(10) 0.09360(10) 0.0560(10) Uani N2 0.31420(10) 0.0911(2) -0.08330(10) 0.0850(10) Uani C1 0.35980(10) 0.3342(2) 0.13780(10) 0.0560(10) Uani C2 0.41100(10) 0.4413(2) 0.12850(10) 0.0730(10) Uani C3 0.49480(10) 0.4356(2) 0.1482(2) 0.090(2) Uani C4 0.52860(10) 0.3240(2) 0.1769(2) 0.094(2) Uani C5 0.47950(10) 0.2181(2) 0.18530(10) 0.0760(10) Uani C6 0.39460(10) 0.2210(2) 0.16590(10) 0.0560(10) Uani C7 0.33960(10) 0.1049(2) 0.17270(10) 0.0630(10) Uani C8 0.38460(10) 0.0111(2) 0.04060(10) 0.0640(10) Uani C9 0.35400(10) -0.0186(2) -0.04430(10) 0.0800(10) Uani C10 0.3745(2) 0.1893(3) -0.1028(2) 0.139(3) Uani C11 0.2701(2) 0.0516(4) -0.1578(2) 0.155(3) Uani C12 0.4138(2) 0.6557(3) 0.0791(2) 0.137(3) Uani HO1 0.255(2) 0.416(3) 0.1130(10) 0.104(8) Uiso HN1 0.2860(10) 0.101(2) 0.0690(10) 0.050(5) Uiso H3 0.5293 0.5088 0.1420 0.108 Uiso H4 0.5865 0.3203 0.1910 0.113 Uiso H5 0.5040 0.1412 0.2047 0.091 Uiso H7a 0.3694 0.0422 0.2033 0.075 Uiso H7b 0.2901 0.1280 0.2019 0.075 Uiso H8a 0.4110 -0.0621 0.0632 0.077 Uiso H8b 0.4240 0.0789 0.0378 0.077 Uiso H9a 0.4003 -0.0448 -0.0772 0.095 Uiso H9b 0.3142 -0.0859 -0.0410 0.095 Uiso H10a 0.3485 0.2607 -0.1283 0.167 Uiso H10b 0.4154 0.1554 -0.1395 0.167 Uiso H10c 0.4010 0.2161 -0.0531 0.167 Uiso H11a 0.2441 0.1231 -0.1831 0.185 Uiso H11b 0.2282 -0.0092 -0.1436 0.185 Uiso H11c 0.3089 0.0144 -0.1952 0.185 Uiso H12a 0.3853 0.7291 0.0593 0.164 Uiso H12b 0.4525 0.6318 0.0371 0.164 Uiso H12c 0.4437 0.6811 0.1272 0.164 Uiso loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 O2 C12 120.9(2) yes C7 N1 C8 114.4(2) yes C10 N2 C11 110.2(2) no C9 N2 C10 111.8(2) no C9 N2 C11 110.0(2) no O1 C1 C6 118.3(2) yes O1 C1 C2 122.2(2) yes C2 C1 C6 119.5(2) no O2 C2 C3 125.2(2) yes O2 C2 C1 114.4(2) yes C1 C2 C3 120.4(2) no C2 C3 C4 119.8(2) no C3 C4 C5 120.5(2) no C4 C5 C6 121.1(2) no C1 C6 C5 118.8(2) no C5 C6 C7 122.1(2) no C1 C6 C7 119.2(2) yes N1 C7 C6 115.00(10) yes N1 C8 C9 110.3(2) no N2 C9 C8 112.0(2) no C1 O1 HO1 114(2) no C8 N1 HN1 109.0(10) no C7 N1 HN1 108.0(10) no C4 C3 H3 120.1 no C2 C3 H3 120.1 no C5 C4 H4 119.8 no C3 C4 H4 119.8 no C4 C5 H5 119.5 no C6 C5 H5 119.5 no H7a C7 H7b 109.5 no N1 C7 H7a 108.1 no C6 C7 H7a 108.1 no N1 C7 H7b 108.1 no C6 C7 H7b 108.1 no H8a C8 H8b 109.5 no N1 C8 H8a 109.2 no C9 C8 H8a 109.2 no N1 C8 H8b 109.3 no C9 C8 H8b 109.3 no H9a C9 H9b 109.5 no N2 C9 H9a 108.8 no C8 C9 H9a 108.8 no N2 C9 H9b 108.8 no C8 C9 H9b 108.9 no H10b C10 H10c 109.5 no H10a C10 H10b 108.9 no N2 C10 H10b 108.9 no H10a C10 H10c 108.9 no N2 C10 H10c 108.9 no N2 C10 H10a 111.7 no H11a C11 H11b 109.4 no H11b C11 H11c 109.5 no N2 C11 H11b 109.3 no H11a C11 H11c 109.4 no N2 C11 H11a 110.0 no N2 C11 H11c 109.3 no H12a C12 H12b 106.6 no H12a C12 H12c 106.5 no O2 C12 H12a 120.8 no H12b C12 H12c 109.5 no O2 C12 H12b 106.6 no O2 C12 H12c 106.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . . 1.348(2) yes O2 C2 . . 1.369(2) yes O2 C12 . . 1.379(3) yes N1 C8 . . 1.460(2) yes N1 C7 . . 1.463(3) yes N2 C10 . . 1.444(4) no N2 C11 . . 1.452(4) no N2 C9 . . 1.459(3) no C1 C6 . . 1.388(2) no C1 C2 . . 1.397(3) no C2 C3 . . 1.372(3) no C3 C4 . . 1.370(3) no C4 C5 . . 1.365(3) no C5 C6 . . 1.387(3) no C6 C7 . . 1.505(3) yes C8 C9 . . 1.488(3) no O1 HO1 . . 0.92(3) no N1 HN1 . . 0.81(2) no C3 H3 . . 0.950 no C4 H4 . . 0.950 no C5 H5 . . 0.950 no C7 H7a . . 0.950 no C7 H7b . . 0.950 no C8 H8a . . 0.950 no C8 H8b . . 0.950 no C9 H9a . . 0.950 no C9 H9b . . 0.950 no C10 H10b . . 0.950 no C10 H10c . . 0.950 no C10 H10a . . 0.950 no C11 H11b . . 0.950 no C11 H11a . . 0.950 no C11 H11c . . 0.950 no C12 H12a . . 0.950 no C12 H12b . . 0.950 no C12 H12c . . 0.950 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag O1 N1 3.111(2) no 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 _geom_torsion_publ_flag C1 C6 C7 N1 71.2(2) no