#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/72/2007268.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_2007268 loop_ _publ_author_name 'Kandasamy Chinnakali' 'Hoong-Kun Fun' 'Kamaraj Sriraghavan' 'Vayalakkavoor T.Ramakrishnan' _publ_section_title ; \b-Hydroxy-N-(4-nitrophenyl)phenethylamine ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9800012 _journal_paper_doi 10.1107/S0108270198099685 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C14 H14 N2 O3' _chemical_formula_sum 'C14 H14 N2 O3' _chemical_formula_weight 258.27 _chemical_name_systematic ; 2-hydroxy-N-(4-nitrophenyl)phenethylamine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 99.6130(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.2820(2) _cell_length_b 7.83960(10) _cell_length_c 20.2459(4) _cell_measurement_reflns_used 4935 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 33.0 _cell_measurement_theta_min 1.50 _cell_volume 1296.06(4) _computing_cell_refinement 'SAINT (Siemens, 1996b)' _computing_data_collection 'SMART (Siemens, 1996a)' _computing_data_reduction 'SAINT (Siemens, 1994b)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1996)' _computing_publication_material ; SHELXTL (Sheldrick, 1996) PARST (Nardelli, 1995) ; _computing_structure_refinement 'SHELXTL (Sheldrick, 1996)' _computing_structure_solution 'SHELXTL (Sheldrick, 1996)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _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 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 8087 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.79 _diffrn_standards_decay_% 'negligible - see text' _diffrn_standards_interval_count 'at start and end of data collection' _diffrn_standards_number '30 frames' _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_meas ? _exptl_crystal_description parallelepiped _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.253 _refine_diff_density_min -0.133 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.038 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 2944 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_restrained_S_obs 1.084 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_obs .0460 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.2986P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1225 _refine_ls_wR_factor_obs .1101 _reflns_number_observed 2238 _reflns_number_total 2945 _reflns_observed_criterion >2sigma(I) _cod_data_source_file qa0037.cif _cod_data_source_block I _cod_depositor_comments ; 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 'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.2986P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.2986P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2007268 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x+1/2, y+1/2, -z+1/2' 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 .1517(15) .0932(11) .0534(7) .0133(10) .0070(8) .0093(7) O2 .0869(9) .0828(10) .0963(10) .0203(8) -.0170(8) .0147(8) O3 .0564(7) .0769(8) .0539(6) .0062(6) .0130(5) .0143(5) N1 .0725(9) .0575(8) .0677(9) -.0041(7) -.0057(7) .0091(7) N2 .0679(8) .0591(8) .0452(7) .0092(6) .0112(6) -.0022(6) C1 .0530(8) .0483(8) .0530(8) -.0033(6) .0005(6) .0030(6) C2 .0539(9) .0521(9) .0723(10) .0103(7) .0088(7) -.0006(7) C3 .0605(9) .0571(9) .0562(9) .0076(7) .0158(7) -.0079(7) C4 .0497(7) .0465(7) .0475(7) -.0002(6) .0088(6) -.0029(6) C5 .0630(9) .0524(9) .0529(8) .0130(7) .0173(7) .0018(7) C6 .0703(10) .0531(9) .0495(8) .0041(8) .0164(7) -.0006(7) C7 .0579(9) .0624(10) .0478(8) .0039(8) .0033(7) .0045(7) C8 .0541(8) .0604(9) .0392(7) .0036(7) .0059(6) .0065(6) C9 .0525(8) .0551(8) .0480(7) -.0019(7) .0058(6) -.0039(6) C10 .0590(9) .0671(10) .0546(9) .0067(8) .0048(7) .0032(7) C11 .0678(11) .0675(11) .0741(12) .0116(9) -.0051(9) -.0005(9) C12 .0693(11) .0740(13) .0921(14) .0166(10) .0047(10) -.0222(11) C13 .0902(14) .0863(14) .0881(14) .0107(12) .0356(12) -.0185(12) C14 .0852(13) .0728(12) .0645(10) .0078(10) .0244(9) -.0010(9) 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 _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .3625(2) .3066(2) .12328(7) .1006(5) Uani d . 1 . O O2 .5000(2) .1310(2) .07317(7) .0924(5) Uani d . 1 . O O3 .26526(15) .9220(2) -.19726(6) .0620(3) Uani d . 1 . O N1 .4033(2) .2511(2) .07195(8) .0679(4) Uani d . 1 . N N2 .1734(2) .5669(2) -.17267(7) .0572(3) Uani d . 1 . N C1 .3389(2) .3274(2) .00825(7) .0524(4) Uani d . 1 . C C2 .3875(2) .2681(2) -.05027(9) .0596(4) Uani d . 1 . C C3 .3307(2) .3469(2) -.10982(8) .0572(4) Uani d . 1 . C C4 .2241(2) .4884(2) -.11317(7) .0478(3) Uani d . 1 . C C5 .1744(2) .5421(2) -.05318(8) .0552(4) Uani d . 1 . C C6 .2318(2) .4625(2) .00644(8) .0569(4) Uani d . 1 . C C7 .0619(2) .7107(2) -.18186(8) .0567(4) Uani d . 1 . C C8 .1429(2) .8801(2) -.15762(7) .0515(4) Uani d . 1 . C C9 .0168(2) 1.0200(2) -.16012(7) .0522(4) Uani d . 1 . C C10 -.0210(2) 1.1294(2) -.21436(8) .0608(4) Uani d . 1 . C C11 -.1404(2) 1.2545(3) -.21496(10) .0718(5) Uani d . 1 . C C12 -.2234(3) 1.2704(3) -.16223(12) .0795(6) Uani d . 1 . C C13 -.1891(3) 1.1616(3) -.10839(12) .0858(6) Uani d . 1 . C C14 -.0689(3) 1.0370(3) -.10711(10) .0728(5) Uani d . 1 . C H1N2 .204(2) .523(3) -.2089(10) .075(6) Uiso d . 1 . H H1O3 .354(3) .895(3) -.1761(12) .102(8) Uiso d . 1 . H H2 .454(2) .175(3) -.0490(9) .073(5) Uiso d . 1 . H H3 .363(2) .308(3) -.1507(10) .077(5) Uiso d . 1 . H H5 .103(2) .634(2) -.0534(9) .065(5) Uiso d . 1 . H H6 .197(2) .502(2) .0458(9) .068(5) Uiso d . 1 . H H7A .024(2) .722(2) -.2310(9) .067(5) Uiso d . 1 . H H7B -.028(2) .688(2) -.1599(8) .058(4) Uiso d . 1 . H H8 .1951(18) .8656(19) -.1108(8) .051(4) Uiso d . 1 . H H10 .034(2) 1.120(2) -.2519(10) .072(5) Uiso d . 1 . H H11 -.160(3) 1.328(3) -.2529(11) .088(6) Uiso d . 1 . H H12 -.302(3) 1.359(3) -.1616(11) .093(7) Uiso d . 1 . H H13 -.248(3) 1.166(3) -.0712(12) .111(8) Uiso d . 1 . H H14 -.045(3) .960(3) -.0716(11) .085(6) Uiso d . 1 . H 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 _geom_angle_publ_flag O1 N1 O2 121.6(2) yes O1 N1 C1 119.9(2) yes O2 N1 C1 118.5(2) yes C4 N2 C7 124.31(13) yes C6 C1 C2 120.64(14) ? C6 C1 N1 118.92(14) ? C2 C1 N1 120.42(15) ? C3 C2 C1 119.60(15) ? C2 C3 C4 121.17(15) ? N2 C4 C5 122.54(14) ? N2 C4 C3 119.87(13) ? C5 C4 C3 117.60(14) ? C6 C5 C4 120.94(15) ? C5 C6 C1 120.01(15) ? N2 C7 C8 113.45(13) ? O3 C8 C9 111.41(12) ? O3 C8 C7 109.41(13) ? C9 C8 C7 110.86(12) ? C10 C9 C14 118.4(2) ? C10 C9 C8 122.62(14) ? C14 C9 C8 118.93(15) ? C9 C10 C11 120.6(2) ? C12 C11 C10 120.4(2) ? C11 C12 C13 119.8(2) ? C12 C13 C14 120.2(2) ? C9 C14 C13 120.6(2) ? 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 N1 . 1.226(2) yes O2 N1 . 1.233(2) yes O3 C8 . 1.432(2) yes N1 C1 . 1.441(2) yes N2 C4 . 1.356(2) yes N2 C7 . 1.449(2) yes C1 C6 . 1.378(2) ? C1 C2 . 1.393(2) ? C2 C3 . 1.366(2) ? C3 C4 . 1.412(2) ? C4 C5 . 1.410(2) ? C5 C6 . 1.371(2) ? C7 C8 . 1.531(2) ? C8 C9 . 1.510(2) ? C9 C10 . 1.387(2) ? C9 C14 . 1.388(2) ? C10 C11 . 1.391(2) ? C11 C12 . 1.369(3) ? C12 C13 . 1.376(3) ? C13 C14 . 1.391(3) ? 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 N2 H1N2 O3 4_544 0.88(2) 2.11(2) 2.988(2) 170(2) yes O3 H1O3 O2 3_665 0.81(2) 2.24(2) 2.938(2) 144(2) yes C2 H2 O2 3_655 0.91(2) 2.49(2) 3.319(2) 151(2) yes C8 H8 O2 3_665 0.98(2) 2.51(2) 3.161(2) 123.0(10) 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 O1 N1 C1 C6 0.0(2) O2 N1 C1 C6 -179.5(2) O1 N1 C1 C2 178.4(2) O2 N1 C1 C2 -1.1(2) C6 C1 C2 C3 1.3(2) N1 C1 C2 C3 -177.13(15) C1 C2 C3 C4 0.4(3) C7 N2 C4 C5 -1.1(2) C7 N2 C4 C3 178.78(14) C2 C3 C4 N2 178.2(2) C2 C3 C4 C5 -1.9(2) N2 C4 C5 C6 -178.2(2) C3 C4 C5 C6 1.9(2) C4 C5 C6 C1 -0.3(3) C2 C1 C6 C5 -1.3(3) N1 C1 C6 C5 177.13(15) C4 N2 C7 C8 77.1(2) N2 C7 C8 O3 64.1(2) N2 C7 C8 C9 -172.59(12) O3 C8 C9 C10 27.6(2) C7 C8 C9 C10 -94.5(2) O3 C8 C9 C14 -154.52(15) C7 C8 C9 C14 83.4(2) C14 C9 C10 C11 0.9(3) C8 C9 C10 C11 178.8(2) C9 C10 C11 C12 -0.6(3) C10 C11 C12 C13 -0.2(3) C11 C12 C13 C14 0.8(3) C10 C9 C14 C13 -0.4(3) C8 C9 C14 C13 -178.3(2) C12 C13 C14 C9 -0.5(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9098450 2 PubChem 124398212