#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008196.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_2008196 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 'C11 H17 Cl N2 O' _chemical_formula_weight 228.73 _chemical_melting_point 336.5(15) _chemical_name_systematic ; 2-[2-(dimethylamino)ethylaminomethyl]-4-chlorophenol ; _space_group_IT_number 60 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _atom_type_scat_source IntTabIV _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_formula_units_Z 8 _cell_length_a 21.9350(10) _cell_length_b 11.4354(7) _cell_length_c 9.9743(6) _cell_measurement_reflns_used 5045 _cell_measurement_temperature 295 _cell_measurement_theta_max 26.8 _cell_measurement_theta_min 2.9 _cell_volume 2501.9(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 295 _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 0.046 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 14436 _diffrn_reflns_reduction_process 14436 _diffrn_reflns_theta_max 26.8 _diffrn_reflns_theta_min 2.9 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.283 _exptl_absorpt_correction_T_max 0.951 _exptl_absorpt_correction_T_min 0.822 _exptl_absorpt_correction_type 'multi-scan (SADABS; Siemens, 1995)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.214 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.23(4) _refine_diff_density_min -0.23(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.295 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 144 _refine_ls_number_reflns 1499 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.041 _refine_ls_shift/esd_max 0.0033 _refine_ls_shift/esd_mean 0.0004 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/{[\s~cs~(F^2^)+1.03F^2^]^1/2^-|F|}^2^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.046 _reflns_number_observed 1499 _reflns_number_total 2569 _reflns_observed_criterion I>2\s(I) _cod_data_source_file sk1230.cif _cod_data_source_block 1a _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '335-338K' was changed to '336.5(15)' - the average value was taken and precision was estimated. '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 15 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '335-338K' was changed to '336.5(15)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana Adding the _atom_site_type_symbol data item to prevent confusion between hydrogen and holmium. Andrius Merkys 2013-10-15 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^)+1.03F^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^)+1.03F^2^]^1/2^-|F|}^2^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2008196 _cod_database_fobs_code 2008196 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,1/2-y,1/2+z 1/2+x,1/2-y,-z -x,+y,1/2-z -x,-y,-z 1/2+x,1/2+y,1/2-z 1/2-x,1/2+y,+z +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 Cl 0.1080(6) 0.0416(4) 0.0664(5) -0.0031(4) 0.0002(4) -0.0112(3) O1 0.0920(10) 0.0390(10) 0.0420(10) 0.0120(10) 0.0140(10) 0.0100(10) C1 0.0470(10) 0.0400(10) 0.0360(10) 0.0060(10) 0.0040(10) 0.0020(10) C2 0.066(2) 0.052(2) 0.0310(10) 0.0060(10) 0.0050(10) 0.0040(10) C3 0.064(2) 0.056(2) 0.0340(10) 0.0040(10) 0.0020(10) -0.0100(10) C4 0.052(2) 0.0400(10) 0.0430(10) -0.0010(10) -0.0010(10) -0.0070(10) C5 0.0470(10) 0.0420(10) 0.0370(10) -0.0010(10) 0.0000(10) 0.0040(10) C6 0.0400(10) 0.0410(10) 0.0310(10) 0.0030(10) 0.0030(10) 0.0000(10) C7 0.058(2) 0.0430(10) 0.0370(10) 0.0040(10) 0.0120(10) 0.0000(10) N1 0.073(2) 0.0370(10) 0.0360(10) 0.0020(10) 0.0070(10) -0.0010(10) C8 0.083(2) 0.049(2) 0.049(2) 0.0000(10) -0.0070(10) 0.0050(10) C9 0.085(2) 0.061(2) 0.064(2) -0.006(2) -0.020(2) -0.0030(10) N2 0.072(2) 0.0510(10) 0.070(2) -0.0090(10) -0.0100(10) 0.0060(10) C10 0.099(3) 0.084(2) 0.081(2) 0.005(2) 0.006(2) 0.007(2) C11 0.094(3) 0.076(2) 0.133(3) -0.023(2) -0.017(2) 0.014(2) loop_ _atom_site_type_symbol _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 Cl Cl 0.92040(4) 0.55243(5) 1.16671(7) 0.0720(5) Uani O O1 0.92920(10) 0.04020(10) 1.1492(2) 0.0580(10) Uani C C1 0.92690(10) 0.1580(2) 1.1587(2) 0.0410(10) Uani C C2 0.91510(10) 0.2168(2) 1.2776(2) 0.050(2) Uani C C3 0.91330(10) 0.3374(2) 1.2806(2) 0.051(2) Uani C C4 0.92330(10) 0.3994(2) 1.1647(2) 0.0450(10) Uani C C5 0.93560(10) 0.3424(2) 1.0459(2) 0.0420(10) Uani C C6 0.93810(10) 0.2214(2) 1.0413(2) 0.0370(10) Uani C C7 0.95150(10) 0.1563(2) 0.9135(2) 0.0460(10) Uani N N1 0.89950(10) 0.0892(2) 0.8605(2) 0.0490(10) Uani C C8 0.85010(10) 0.1637(2) 0.8096(2) 0.060(2) Uani C C9 0.79150(10) 0.0951(2) 0.8021(3) 0.070(2) Uani N N2 0.77240(10) 0.0515(2) 0.9324(3) 0.064(2) Uani C C10 0.74970(10) 0.1441(3) 1.0171(3) 0.088(2) Uani C C11 0.7269(2) -0.0402(3) 0.9182(4) 0.101(3) Uani H HN1 0.8850(10) 0.053(2) 0.923(2) 0.044(8) Uiso H HO1 0.9190(10) 0.006(3) 1.228(3) 0.083(10) Uiso H H2 0.9083 0.1737 1.3576 0.060 Uiso H H3 0.9053 0.3772 1.3623 0.061 Uiso H H5 0.9425 0.3865 0.9666 0.050 Uiso H H7a 0.9636 0.2115 0.8475 0.056 Uiso H H7b 0.9840 0.1035 0.9302 0.056 Uiso H H8a 0.8448 0.2285 0.8680 0.072 Uiso H H8b 0.8605 0.1911 0.7226 0.072 Uiso H H9a 0.7604 0.1445 0.7676 0.084 Uiso H H9b 0.7972 0.0306 0.7435 0.084 Uiso H H10a 0.7372 0.1155 1.1023 0.106 Uiso H H10b 0.7810 0.2004 1.0295 0.106 Uiso H H10c 0.7157 0.1798 0.9744 0.106 Uiso H H11a 0.7144 -0.0687 1.0034 0.122 Uiso H H11b 0.6924 -0.0095 0.8725 0.122 Uiso H H11c 0.7437 -0.1028 0.8677 0.122 Uiso 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 O1 C1 C2 . 123.4(2) yes O1 C1 C6 . 116.8(2) yes C2 C1 C6 . 119.8(2) no C1 C2 C3 . 120.5(2) no C2 C3 C4 . 119.6(2) no C3 C4 C5 . 120.7(2) no Cl C4 C3 . 120.0(2) yes Cl C4 C5 . 119.3(2) yes C4 C5 C6 . 120.5(2) no C1 C6 C5 . 118.9(2) no C5 C6 C7 . 122.0(2) no C1 C6 C7 . 119.1(2) yes C6 C7 N1 . 114.2(2) yes C7 N1 C8 . 113.1(2) yes N1 C8 C9 . 110.1(2) yes C8 C9 N2 . 112.3(2) no C9 N2 C10 . 111.8(2) no C10 N2 C11 . 110.3(3) no C9 N2 C11 . 111.0(3) no C1 O1 HO1 . 111(2) no C3 C2 H2 . 119.7 no C1 C2 H2 . 119.7 no C4 C3 H3 . 120.2 no C2 C3 H3 . 120.2 no C4 C5 H5 . 119.7 no C6 C5 H5 . 119.7 no H7a C7 H7b . 109.5 no N1 C7 H7a . 108.3 no C6 C7 H7a . 108.3 no N1 C7 H7b . 108.3 no C6 C7 H7b . 108.3 no C8 N1 HN1 . 106(2) no C7 N1 HN1 . 107(2) no HN1 N1 HO1 8_554 111(2) no C8 N1 HO1 8_554 106.3 no C7 N1 HO1 8_554 113.6 no H8a C8 H8b . 109.5 no N1 C8 H8a . 109.3 no C9 C8 H8a . 109.3 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 . 108.8 no H10a C10 H10b . 108.9 no H10a C10 H10c . 108.9 no N2 C10 H10a . 111.8 no H10b C10 H10c . 109.5 no N2 C10 H10b . 108.9 no N2 C10 H10c . 108.9 no H11a C11 H11b . 109.1 no H11a C11 H11c . 109.1 no N2 C11 H11a . 111.0 no H11b C11 H11c . 109.5 no N2 C11 H11b . 109.1 no N2 C11 H11c . 109.1 no O1 HO1 N1 8_555 167(3) 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 Cl C4 . . 1.751(2) yes O1 C1 . . 1.352(3) yes C1 C2 . . 1.387(3) no C1 C6 . . 1.399(3) no C2 C3 . . 1.379(3) no C3 C4 . . 1.374(3) no C4 C5 . . 1.379(3) no C5 C6 . . 1.385(3) no C6 C7 . . 1.505(3) yes C7 N1 . . 1.472(3) yes N1 C8 . . 1.469(3) yes C8 C9 . . 1.509(4) no C9 N2 . . 1.454(4) no N2 C10 . . 1.443(4) no N2 C11 . . 1.456(4) no O1 HO1 . . 0.90(3) no C2 H2 . . 0.950 no C3 H3 . . 0.950 no C5 H5 . . 0.950 no C7 H7a . . 0.950 no C7 H7b . . 0.950 no N1 HN1 . . 0.81(2) no N1 HO1 . 8_554 1.77(3) no C8 H8a . . 0.950 no C8 H8b . . 0.950 no C9 H9a . . 0.950 no C9 H9b . . 0.950 no C10 H10a . . 0.950 no C10 H10b . . 0.950 no C10 H10c . . 0.950 no C11 H11a . . 0.950 no C11 H11b . . 0.950 no C11 H11c . . 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 3.005(3) 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 67.5(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 3943429