#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:48:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011362.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_2011362 loop_ _publ_author_name 'Lynch, Daniel E.' 'Byriel, Karl A.' _publ_section_title ; 3,5-Dimethyl-4-(2,4,6-trimethylphenyldiazenyl)phenol ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first e400 _journal_page_last e400 _journal_paper_doi 10.1107/S0108270100010519 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C17 H20 N2 O' _chemical_formula_weight 268.35 _chemical_name_systematic ; 4-(2,4,6-Trimethyl)phenylazo(3,5-dimethyl)phenol ; _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-97 _cell_angle_alpha 90.00 _cell_angle_beta 101.842(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.369(2) _cell_length_b 7.6809(3) _cell_length_c 15.332(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 14 _cell_measurement_theta_min 6 _cell_volume 1425.6(4) _computing_cell_refinement MolEN _computing_data_collection 'MolEN (Fair, 1990)' _computing_data_reduction 'Xtal3.2 (Hall et al., 1992)' _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 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method 2\q/\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .019 _diffrn_reflns_av_sigmaI/netI .0288 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2679 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 1.93 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .078 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 576 _exptl_crystal_size_max .47 _exptl_crystal_size_mid .47 _exptl_crystal_size_min .47 _refine_diff_density_max .19 _refine_diff_density_min -.16 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 2512 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all .073 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max .005 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.3065P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .127 _reflns_number_gt 1717 _reflns_number_total 2512 _reflns_threshold_expression I>2\s(I) _cod_data_source_file qd0004.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2011362 _cod_database_fobs_code 2011362 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_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 O1 .53687(12) -.0420(2) .22413(11) .0590(5) Uani d . 1 . . O H1 .552(2) -.103(4) .2731(17) .085(9) Uiso d . 1 . . H N1 .89937(13) .1363(2) .07926(9) .0397(4) Uani d . 1 . . N N2 .97766(12) .2192(2) .12515(10) .0388(4) Uani d . 1 . . N C1 .81126(15) .0945(2) .12329(11) .0365(4) Uani d . 1 . . C C2 .82765(15) .0203(3) .20881(12) .0388(5) Uani d . 1 . . C C21 .94033(16) -.0194(3) .26474(14) .0529(6) Uani d . 1 . . C H21 .9894 -.0526 .2266 .068(7) Uiso calc R 1 . . H H22 .9344 -.1130 .3050 .076(8) Uiso calc R 1 . . H H23 .9688 .0823 .2982 .072(8) Uiso calc R 1 . . H C3 .73567(16) -.0281(3) .24174(12) .0421(5) Uani d . 1 . . C H3 .7456 -.0802 .2976 .047(6) Uiso calc R 1 . . H C4 .62962(15) -.0008(3) .19358(12) .0421(5) Uani d . 1 . . C C5 .61505(16) .0692(3) .10833(12) .0432(5) Uani d . 1 . . C H5 .5439 .0881 .0758 .048(6) Uiso calc R 1 . . H C6 .70404(15) .1111(2) .07118(12) .0388(5) Uani d . 1 . . C C61 .68632(17) .1697(3) -.02481(13) .0516(6) Uani d . 1 . . C H61 .7171 .2838 -.0274 .071(7) Uiso calc R 1 . . H H62 .6086 .1727 -.0501 .069(7) Uiso calc R 1 . . H H63 .7220 .0897 -.0579 .089(9) Uiso calc R 1 . . H C7 1.06864(15) .2543(2) .08298(12) .0364(4) Uani d . 1 . . C C8 1.05930(15) .2815(2) -.00945(12) .0381(4) Uani d . 1 . . C C81 .95173(16) .2771(3) -.07651(12) .0472(5) Uani d . 1 . . C H81 .9626 .3239 -.1321 .051(6) Uiso calc R 1 . . H H82 .8977 .3455 -.0550 .062(7) Uiso calc R 1 . . H H83 .9264 .1590 -.0851 .055(6) Uiso calc R 1 . . H C9 1.15469(16) .3193(3) -.03952(13) .0427(5) Uani d . 1 . . C H9 1.1493 .3394 -.1001 .039(5) Uiso calc R 1 . . H C10 1.25801(16) .3286(3) .01646(13) .0434(5) Uani d . 1 . . C C101 1.35980(18) .3666(4) -.02048(17) .0594(6) Uani d . 1 . . C H101 1.3667 .2810 -.0646 .132(13) Uiso calc R 1 . . H H102 1.4240 .3628 .0269 .120(11) Uiso calc R 1 . . H H103 1.3534 .4802 -.0472 .141(14) Uiso calc R 1 . . H C11 1.26454(16) .3014(3) .10639(13) .0470(5) Uani d . 1 . . C H11 1.3333 .3062 .1448 .061(7) Uiso calc R 1 . . H C12 1.17204(15) .2672(3) .14124(12) .0422(5) Uani d . 1 . . C C121 1.18669(18) .2395(4) .24080(13) .0632(7) Uani d . 1 . . C H121 1.2623 .2610 .2690 .091(9) Uiso calc R 1 . . H H122 1.1676 .1217 .2522 .139(14) Uiso calc R 1 . . H H123 1.1395 .3182 .2643 .128(13) 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 .0452(8) .0788(12) .0553(9) -.0085(8) .0153(7) .0175(9) N1 .0442(9) .0411(9) .0344(8) -.0028(7) .0096(7) .0006(7) N2 .0381(8) .0440(9) .0336(8) .0008(7) .0059(7) -.0012(7) C1 .0431(10) .0355(10) .0320(9) -.0008(8) .0106(8) -.0037(8) C2 .0425(11) .0385(11) .0352(10) .0005(8) .0078(8) -.0009(8) C21 .0469(12) .0667(15) .0456(12) .0059(11) .0106(10) .0167(12) C3 .0503(11) .0421(11) .0339(10) -.0018(9) .0089(8) .0046(8) C4 .0445(11) .0423(11) .0414(10) -.0072(9) .0135(9) -.0001(9) C5 .0407(11) .0448(12) .0411(11) -.0053(9) .0016(9) .0000(9) C6 .0459(11) .0356(10) .0340(9) -.0054(8) .0058(8) -.0025(8) C61 .0520(13) .0597(14) .0400(11) -.0084(11) .0023(10) .0071(10) C7 .0385(10) .0369(10) .0356(9) .0004(8) .0116(8) -.0045(8) C8 .0437(11) .0369(10) .0343(9) .0002(8) .0095(8) -.0030(8) C81 .0504(12) .0570(14) .0344(10) -.0053(10) .0093(9) .0035(9) C9 .0513(12) .0425(12) .0372(10) -.0017(9) .0157(9) -.0022(8) C10 .0447(11) .0392(11) .0492(11) .0013(9) .0167(9) -.0039(9) C101 .0500(13) .0676(17) .0675(15) -.0028(11) .0283(12) -.0030(13) C11 .0378(11) .0527(13) .0499(12) .0011(9) .0073(9) -.0043(10) C12 .0406(11) .0474(12) .0385(10) .0026(9) .0079(8) -.0010(9) C121 .0452(13) .103(2) .0387(11) -.0004(13) .0012(9) .0057(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C4 O1 H1 112.0(17) N2 N1 C1 115.22(14) N1 N2 C7 115.57(14) C2 C1 C6 120.35(17) C2 C1 N1 123.55(16) C6 C1 N1 115.61(15) C3 C2 C1 118.44(17) C3 C2 C21 118.00(17) C1 C2 C21 123.46(17) C2 C21 H21 109.5 C2 C21 H22 109.5 H21 C21 H22 109.5 C2 C21 H23 109.5 H21 C21 H23 109.5 H22 C21 H23 109.5 C4 C3 C2 121.61(17) C4 C3 H3 119.2 C2 C3 H3 119.2 O1 C4 C3 123.69(17) O1 C4 C5 117.20(17) C3 C4 C5 119.10(18) C6 C5 C4 121.24(17) C6 C5 H5 119.4 C4 C5 H5 119.4 C5 C6 C1 118.97(17) C5 C6 C61 120.25(17) C1 C6 C61 120.77(17) C6 C61 H61 109.5 C6 C61 H62 109.5 H61 C61 H62 109.5 C6 C61 H63 109.5 H61 C61 H63 109.5 H62 C61 H63 109.5 C12 C7 C8 120.22(16) C12 C7 N2 115.01(15) C8 C7 N2 124.73(16) C9 C8 C7 117.74(17) C9 C8 C81 118.16(16) C7 C8 C81 124.07(16) C8 C81 H81 109.5 C8 C81 H82 109.5 H81 C81 H82 109.5 C8 C81 H83 109.5 H81 C81 H83 109.5 H82 C81 H83 109.5 C8 C9 C10 123.04(18) C8 C9 H9 118.5 C10 C9 H9 118.5 C11 C10 C9 117.89(17) C11 C10 C101 121.41(19) C9 C10 C101 120.70(19) C10 C101 H101 109.5 C10 C101 H102 109.5 H101 C101 H102 109.5 C10 C101 H103 109.5 H101 C101 H103 109.5 H102 C101 H103 109.5 C10 C11 C12 122.07(18) C10 C11 H11 119.0 C12 C11 H11 119.0 C11 C12 C7 119.00(17) C11 C12 C121 118.58(18) C7 C12 C121 122.39(17) C12 C121 H121 109.5 C12 C121 H122 109.5 H121 C121 H122 109.5 C12 C121 H123 109.5 H121 C121 H123 109.5 H122 C121 H123 109.5 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 C4 . 1.362(2) ? O1 H1 . .87(3) ? N1 N2 . 1.249(2) ? N1 C1 . 1.431(2) ? N2 C7 . 1.434(2) ? C1 C2 . 1.406(2) ? C1 C6 . 1.407(3) ? C2 C3 . 1.387(3) ? C2 C21 . 1.510(3) ? C21 H21 . .9600 ? C21 H22 . .9600 ? C21 H23 . .9600 ? C3 C4 . 1.383(3) ? C3 H3 . .9300 ? C4 C5 . 1.391(3) ? C5 C6 . 1.377(3) ? C5 H5 . .9300 ? C6 C61 . 1.511(2) ? C61 H61 . .9600 ? C61 H62 . .9600 ? C61 H63 . .9600 ? C7 C12 . 1.405(3) ? C7 C8 . 1.414(2) ? C8 C9 . 1.383(3) ? C8 C81 . 1.506(3) ? C81 H81 . .9600 ? C81 H82 . .9600 ? C81 H83 . .9600 ? C9 C10 . 1.387(3) ? C9 H9 . .9300 ? C10 C11 . 1.380(3) ? C10 C101 . 1.511(3) ? C101 H101 . .9600 ? C101 H102 . .9600 ? C101 H103 . .9600 ? C11 C12 . 1.384(3) ? C11 H11 . .9300 ? C12 C121 . 1.515(3) ? C121 H121 . .9600 ? C121 H122 . .9600 ? C121 H123 . .9600 ? 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 O1 H1 N2 2_645 .87(3) 2.16(3) 2.985(2) 157(2) 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 C1 N1 N2 C7 177.16(15) N2 N1 C1 C2 -48.4(3) N2 N1 C1 C6 139.63(17) C6 C1 C2 C3 -3.0(3) N1 C1 C2 C3 -174.63(17) C6 C1 C2 C21 173.29(19) N1 C1 C2 C21 1.6(3) C1 C2 C3 C4 -1.7(3) C21 C2 C3 C4 -178.19(19) C2 C3 C4 O1 -178.22(19) C2 C3 C4 C5 3.1(3) O1 C4 C5 C6 -178.53(18) C3 C4 C5 C6 .2(3) C4 C5 C6 C1 -4.8(3) C4 C5 C6 C61 173.73(19) C2 C1 C6 C5 6.2(3) N1 C1 C6 C5 178.47(17) C2 C1 C6 C61 -172.33(18) N1 C1 C6 C61 .0(3) N1 N2 C7 C12 -150.46(17) N1 N2 C7 C8 31.8(3) C12 C7 C8 C9 .5(3) N2 C7 C8 C9 178.08(18) C12 C7 C8 C81 -177.63(19) N2 C7 C8 C81 -.1(3) C7 C8 C9 C10 1.1(3) C81 C8 C9 C10 179.31(19) C8 C9 C10 C11 -1.1(3) C8 C9 C10 C101 178.7(2) C9 C10 C11 C12 -.5(3) C101 C10 C11 C12 179.7(2) C10 C11 C12 C7 2.0(3) C10 C11 C12 C121 -179.8(2) C8 C7 C12 C11 -2.0(3) N2 C7 C12 C11 -179.81(17) C8 C7 C12 C121 179.9(2) N2 C7 C12 C121 2.1(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30652306