# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Gautam R. Desiraju' _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad 500 046, India ; _publ_contact_author_email 'gautam desiraju@yahoo.com' _publ_contact_author_phone '91 40 23134828' _publ_contact_author_fax '91 40 23010567' _publ_section_title ; Correlation between molecular dipole moment and centrosymmetry in some crystalline diphenyl ethers. ; _publ_section_abstract ; The presence of a large molecular dipole moment in diphenyl ethers leads unequivocally to a centrosymmetric crystal structure. ; loop_ _publ_author_name _publ_author_address 'Archan Dey' ;School of Chemistry University of Hyderabad Hyderabad 500 046, India ; 'Gautam R. Desiraju' ;School of Chemistry University of Hyderabad Hyderabad 500 046, India ; data_1 _database_code_depnum_ccdc_archive 'CCDC 264996' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-methoxyphenoxy)aniline ; _chemical_name_common 4-(4-methoxyphenoxy)aniline _chemical_melting_point 352 _chemical_formula_moiety 'C13 H13 N O2' _chemical_formula_sum 'C13 H13 N O2' _chemical_formula_weight 215.24 _chemical_absolute_configuration unk 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5729(5) _cell_length_b 5.4503(4) _cell_length_c 13.4175(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.077(2) _cell_angle_gamma 90.00 _cell_volume 552.40(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1564 _cell_measurement_theta_min 2.6965 _cell_measurement_theta_max 27.3965 _exptl_crystal_description Block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min 0 _exptl_absorpt_correction_T_max 0 _exptl_absorpt_process_details . _exptl_special_details ; Microsource radiation ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bede Microsource' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3975 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2388 _reflns_number_gt 1989 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.2(11) _refine_ls_number_reflns 2388 _refine_ls_number_parameters 197 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0713 _refine_ls_wR_factor_gt 0.0691 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C8 C 0.51702(17) 0.3711(3) 0.33279(10) 0.0241(3) Uani 1 1 d . . . C1 C 0.8553(2) 0.1542(3) -0.15206(13) 0.0292(4) Uani 1 1 d . . . N1 N 0.01750(17) 0.4626(3) 0.44199(10) 0.0289(3) Uani 1 1 d . . . O1 O 0.76907(12) 0.3529(2) -0.10623(8) 0.0270(2) Uani 1 1 d . . . O2 O 0.68778(12) 0.3363(2) 0.30039(7) 0.0304(3) Uani 1 1 d . . . C5 C 0.70204(17) 0.3372(3) 0.19707(10) 0.0230(3) Uani 1 1 d . . . C7 C 0.65403(18) 0.5226(3) 0.03581(12) 0.0240(3) Uani 1 1 d . . . C2 C 0.75268(16) 0.3374(3) -0.00536(10) 0.0216(3) Uani 1 1 d . . . C11 C 0.18452(18) 0.4330(3) 0.40462(10) 0.0221(3) Uani 1 1 d . . . C10 C 0.2192(2) 0.2356(3) 0.34266(12) 0.0258(4) Uani 1 1 d . . . C6 C 0.62883(18) 0.5234(3) 0.13639(12) 0.0247(3) Uani 1 1 d . . . C13 C 0.4873(2) 0.5652(3) 0.39511(11) 0.0253(4) Uani 1 1 d . . . C12 C 0.32181(19) 0.5958(3) 0.43095(11) 0.0250(4) Uani 1 1 d . . . C9 C 0.3840(2) 0.2046(3) 0.30662(11) 0.0264(4) Uani 1 1 d . . . C4 C 0.80017(18) 0.1553(3) 0.15690(12) 0.0256(3) Uani 1 1 d . . . C3 C 0.82730(18) 0.1535(3) 0.05557(11) 0.0238(3) Uani 1 1 d . . . H8 H 0.412(2) 0.071(3) 0.2624(11) 0.027(4) Uiso 1 1 d . . . H7 H 0.6048(18) 0.647(3) -0.0073(11) 0.026(4) Uiso 1 1 d . . . H4 H 0.8925(18) 0.021(3) 0.0261(11) 0.020(4) Uiso 1 1 d . . . H10 H 0.2970(19) 0.733(3) 0.4730(11) 0.029(4) Uiso 1 1 d . . . H11 H 0.5793(19) 0.673(4) 0.4119(11) 0.027(4) Uiso 1 1 d . . . H6 H 0.5604(17) 0.647(3) 0.1662(10) 0.017(4) Uiso 1 1 d . . . H5 H 0.845(2) 0.027(4) 0.1994(12) 0.030(4) Uiso 1 1 d . . . H9 H 0.1241(19) 0.122(4) 0.3258(11) 0.032(5) Uiso 1 1 d . . . H2 H 0.982(2) 0.137(3) -0.1283(11) 0.027(4) Uiso 1 1 d . . . H1 H 0.852(2) 0.182(4) -0.2242(13) 0.037(5) Uiso 1 1 d . . . H3 H 0.791(2) -0.003(4) -0.1399(12) 0.032(5) Uiso 1 1 d . . . H13 H 0.000(2) 0.626(4) 0.4679(13) 0.044(5) Uiso 1 1 d . . . H12 H -0.070(2) 0.419(3) 0.4007(13) 0.036(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C8 0.0222(7) 0.0296(9) 0.0203(7) 0.0022(7) 0.0000(6) 0.0032(7) C1 0.0321(9) 0.0315(10) 0.0239(9) -0.0047(7) 0.0029(7) -0.0001(8) N1 0.0229(7) 0.0377(9) 0.0262(7) -0.0030(6) 0.0018(6) -0.0035(6) O1 0.0270(5) 0.0284(6) 0.0256(6) 0.0010(5) 0.0022(4) 0.0028(5) O2 0.0204(5) 0.0454(7) 0.0253(6) -0.0041(6) 0.0004(4) 0.0040(5) C5 0.0177(7) 0.0269(9) 0.0243(8) -0.0042(7) 0.0006(6) -0.0024(7) C7 0.0176(7) 0.0213(8) 0.0328(9) 0.0039(7) -0.0002(6) 0.0008(6) C2 0.0160(7) 0.0234(8) 0.0253(8) 0.0000(7) 0.0000(5) -0.0039(6) C11 0.0226(7) 0.0257(9) 0.0179(7) 0.0046(7) 0.0009(6) 0.0012(6) C10 0.0270(8) 0.0246(8) 0.0257(8) 0.0008(7) 0.0001(6) -0.0052(7) C6 0.0165(7) 0.0235(9) 0.0344(9) -0.0058(7) 0.0038(6) 0.0005(6) C13 0.0236(8) 0.0262(9) 0.0252(8) -0.0007(7) -0.0032(6) -0.0031(7) C12 0.0272(8) 0.0262(9) 0.0213(8) -0.0041(7) -0.0009(6) 0.0012(7) C9 0.0315(9) 0.0236(9) 0.0237(8) -0.0044(7) -0.0014(6) 0.0038(7) C4 0.0224(8) 0.0257(9) 0.0282(9) 0.0023(7) -0.0019(6) 0.0016(7) C3 0.0201(7) 0.0213(8) 0.0300(9) -0.0029(7) 0.0009(6) 0.0020(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C8 C13 1.377(2) . ? C8 C9 1.383(2) . ? C8 O2 1.4061(16) . ? C1 O1 1.426(2) . ? C1 H2 0.994(15) . ? C1 H1 0.978(17) . ? C1 H3 1.005(19) . ? N1 C11 1.4027(18) . ? N1 H13 0.97(2) . ? N1 H12 0.866(17) . ? O1 C2 1.3704(17) . ? O2 C5 1.3981(17) . ? C5 C4 1.372(2) . ? C5 C6 1.391(2) . ? C7 C6 1.376(2) . ? C7 C2 1.393(2) . ? C7 H7 0.951(17) . ? C2 C3 1.388(2) . ? C11 C12 1.393(2) . ? C11 C10 1.396(2) . ? C10 C9 1.381(2) . ? C10 H9 0.964(17) . ? C6 H6 0.954(15) . ? C13 C12 1.384(2) . ? C13 H11 0.926(17) . ? C12 H10 0.964(18) . ? C9 H8 0.971(17) . ? C4 C3 1.389(2) . ? C4 H5 0.951(19) . ? C3 H4 0.975(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 C8 C9 120.73(13) . . ? C13 C8 O2 119.03(13) . . ? C9 C8 O2 120.15(14) . . ? O1 C1 H2 113.4(10) . . ? O1 C1 H1 109.2(12) . . ? H2 C1 H1 106.7(13) . . ? O1 C1 H3 109.6(10) . . ? H2 C1 H3 109.4(15) . . ? H1 C1 H3 108.3(15) . . ? C11 N1 H13 112.5(11) . . ? C11 N1 H12 114.2(11) . . ? H13 N1 H12 111.3(16) . . ? C2 O1 C1 117.09(12) . . ? C5 O2 C8 116.34(10) . . ? C4 C5 C6 120.11(14) . . ? C4 C5 O2 117.98(14) . . ? C6 C5 O2 121.80(14) . . ? C6 C7 C2 120.44(15) . . ? C6 C7 H7 121.2(10) . . ? C2 C7 H7 118.3(9) . . ? O1 C2 C3 124.37(13) . . ? O1 C2 C7 115.83(13) . . ? C3 C2 C7 119.80(13) . . ? C12 C11 C10 118.24(13) . . ? C12 C11 N1 120.78(14) . . ? C10 C11 N1 120.95(14) . . ? C9 C10 C11 121.07(14) . . ? C9 C10 H9 121.2(10) . . ? C11 C10 H9 117.8(10) . . ? C7 C6 C5 119.63(15) . . ? C7 C6 H6 122.0(9) . . ? C5 C6 H6 118.3(9) . . ? C8 C13 C12 119.65(14) . . ? C8 C13 H11 118.7(10) . . ? C12 C13 H11 121.6(10) . . ? C13 C12 C11 120.88(15) . . ? C13 C12 H10 121.1(9) . . ? C11 C12 H10 118.0(9) . . ? C10 C9 C8 119.41(15) . . ? C10 C9 H8 123.0(9) . . ? C8 C9 H8 117.6(9) . . ? C5 C4 C3 120.74(15) . . ? C5 C4 H5 118.5(10) . . ? C3 C4 H5 120.7(10) . . ? C2 C3 C4 119.28(15) . . ? C2 C3 H4 119.6(9) . . ? C4 C3 H4 121.1(9) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 C8 O2 C5 -121.70(15) . . . . ? C9 C8 O2 C5 61.80(19) . . . . ? C8 O2 C5 C4 -133.66(14) . . . . ? C8 O2 C5 C6 50.13(19) . . . . ? C1 O1 C2 C3 5.85(19) . . . . ? C1 O1 C2 C7 -174.37(13) . . . . ? C6 C7 C2 O1 179.68(13) . . . . ? C6 C7 C2 C3 -0.5(2) . . . . ? C12 C11 C10 C9 -1.3(2) . . . . ? N1 C11 C10 C9 -179.31(14) . . . . ? C2 C7 C6 C5 -0.2(2) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? O2 C5 C6 C7 176.74(13) . . . . ? C9 C8 C13 C12 -0.8(2) . . . . ? O2 C8 C13 C12 -177.30(13) . . . . ? C8 C13 C12 C11 -0.2(2) . . . . ? C10 C11 C12 C13 1.2(2) . . . . ? N1 C11 C12 C13 179.24(14) . . . . ? C11 C10 C9 C8 0.3(2) . . . . ? C13 C8 C9 C10 0.7(2) . . . . ? O2 C8 C9 C10 177.19(13) . . . . ? C6 C5 C4 C3 -0.2(2) . . . . ? O2 C5 C4 C3 -176.51(13) . . . . ? O1 C2 C3 C4 -179.33(13) . . . . ? C7 C2 C3 C4 0.9(2) . . . . ? C5 C4 C3 C2 -0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.143 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.032 # END# data_2 _database_code_depnum_ccdc_archive 'CCDC 264997' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-nitrophenoxy)-phenol ; _chemical_name_common 4-(4-nitrophenoxy)-phenol _chemical_melting_point 446 _chemical_formula_moiety 'C12 H9 N O4' _chemical_formula_sum 'C12 H9 N O4' _chemical_formula_weight 231.20 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 11.2437(17) _cell_length_b 5.3306(8) _cell_length_c 17.601(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.891(13) _cell_angle_gamma 90.00 _cell_volume 1051.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.67 _cell_measurement_theta_max 10.45 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius Mach3 four-circle' _diffrn_measurement_method 'Profile data from omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% none _diffrn_reflns_number 2510 _diffrn_reflns_av_R_equivalents 0.0094 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2392 _reflns_number_gt 1674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'WinGX (Farrugia, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.2035P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.021(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2392 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1006 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.35730(11) 0.0552(2) 0.47781(6) 0.0566(3) Uani 1 1 d . . . O1 O 0.45006(11) 0.1721(3) 0.17658(6) 0.0557(3) Uani 1 1 d . . . O4 O 0.03329(13) 0.8973(3) 0.59670(8) 0.0765(4) Uani 1 1 d . . . N1 N 0.10683(13) 0.7627(3) 0.63167(9) 0.0590(4) Uani 1 1 d . . . O3 O 0.13143(13) 0.7812(3) 0.70042(8) 0.0862(5) Uani 1 1 d . . . C1 C 0.43045(13) 0.1506(3) 0.25207(8) 0.0422(4) Uani 1 1 d . . . C2 C 0.36184(16) -0.0480(3) 0.27277(9) 0.0533(4) Uani 1 1 d . . . H2 H 0.3329 -0.1639 0.2363 0.064 Uiso 1 1 calc R . . C3 C 0.33592(15) -0.0756(3) 0.34765(9) 0.0527(4) Uani 1 1 d . . . H3 H 0.2888 -0.2086 0.3615 0.063 Uiso 1 1 calc R . . C4 C 0.37978(14) 0.0933(3) 0.40139(9) 0.0454(4) Uani 1 1 d . . . C5 C 0.45016(15) 0.2893(3) 0.38179(9) 0.0541(4) Uani 1 1 d . . . H5 H 0.4810 0.4017 0.4188 0.065 Uiso 1 1 calc R . . C6 C 0.47500(14) 0.3186(3) 0.30663(9) 0.0504(4) Uani 1 1 d . . . H6 H 0.5219 0.4522 0.2930 0.061 Uiso 1 1 calc R . . C7 C 0.29204(13) 0.2314(3) 0.51215(8) 0.0422(4) Uani 1 1 d . . . C8 C 0.30300(14) 0.2306(3) 0.59133(9) 0.0515(4) Uani 1 1 d . . . H8 H 0.3522 0.1141 0.6178 0.062 Uiso 1 1 calc R . . C9 C 0.24074(14) 0.4029(4) 0.63030(9) 0.0518(4) Uani 1 1 d . . . H9 H 0.2473 0.4040 0.6833 0.062 Uiso 1 1 calc R . . C10 C 0.16852(13) 0.5740(3) 0.59010(8) 0.0446(4) Uani 1 1 d . . . C11 C 0.15394(14) 0.5732(3) 0.51148(8) 0.0465(4) Uani 1 1 d . . . H11 H 0.1031 0.6874 0.4853 0.056 Uiso 1 1 calc R . . C12 C 0.21624(14) 0.3998(3) 0.47247(8) 0.0451(4) Uani 1 1 d . . . H12 H 0.2074 0.3958 0.4195 0.054 Uiso 1 1 calc R . . H1A H 0.480(2) 0.311(5) 0.1683(13) 0.092(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0737(8) 0.0499(7) 0.0493(6) 0.0101(5) 0.0229(6) 0.0138(6) O1 0.0682(8) 0.0556(8) 0.0452(6) -0.0019(6) 0.0161(5) -0.0051(6) O4 0.0751(9) 0.0702(9) 0.0858(10) -0.0164(8) 0.0162(8) 0.0144(8) N1 0.0558(9) 0.0630(10) 0.0601(9) -0.0209(8) 0.0169(7) -0.0117(8) O3 0.0937(10) 0.1093(13) 0.0569(8) -0.0409(8) 0.0147(7) -0.0051(9) C1 0.0427(8) 0.0410(8) 0.0442(8) -0.0001(7) 0.0115(6) 0.0027(7) C2 0.0654(10) 0.0429(9) 0.0525(9) -0.0063(8) 0.0114(8) -0.0093(8) C3 0.0595(10) 0.0395(9) 0.0612(10) 0.0045(8) 0.0174(8) -0.0074(8) C4 0.0512(8) 0.0416(8) 0.0456(8) 0.0056(7) 0.0163(7) 0.0066(7) C5 0.0649(10) 0.0498(10) 0.0491(9) -0.0084(8) 0.0131(8) -0.0109(8) C6 0.0544(9) 0.0463(9) 0.0523(9) 0.0007(8) 0.0149(7) -0.0126(7) C7 0.0448(8) 0.0420(8) 0.0412(8) 0.0020(6) 0.0123(6) -0.0047(7) C8 0.0485(9) 0.0628(11) 0.0430(8) 0.0091(8) 0.0036(7) -0.0002(8) C9 0.0504(9) 0.0720(12) 0.0333(7) -0.0035(8) 0.0047(6) -0.0089(9) C10 0.0431(8) 0.0501(9) 0.0418(8) -0.0099(7) 0.0110(6) -0.0093(7) C11 0.0485(8) 0.0481(9) 0.0435(8) 0.0017(7) 0.0074(7) 0.0000(7) C12 0.0532(9) 0.0500(9) 0.0327(7) 0.0013(7) 0.0073(6) -0.0022(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C7 1.3645(18) . ? O2 C4 1.4045(18) . ? O1 C1 1.3702(18) . ? O1 H1A 0.83(2) . ? O4 N1 1.2210(19) . ? N1 O3 1.2219(19) . ? N1 C10 1.454(2) . ? C1 C6 1.376(2) . ? C1 C2 1.378(2) . ? C2 C3 1.382(2) . ? C2 H2 0.9300 . ? C3 C4 1.367(2) . ? C3 H3 0.9300 . ? C4 C5 1.372(2) . ? C5 C6 1.384(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.385(2) . ? C7 C8 1.389(2) . ? C8 C9 1.373(2) . ? C8 H8 0.9300 . ? C9 C10 1.376(2) . ? C9 H9 0.9300 . ? C10 C11 1.380(2) . ? C11 C12 1.378(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O2 C4 118.18(12) . . ? C1 O1 H1A 110.2(16) . . ? O4 N1 O3 122.56(16) . . ? O4 N1 C10 118.98(15) . . ? O3 N1 C10 118.46(17) . . ? O1 C1 C6 122.92(14) . . ? O1 C1 C2 117.43(14) . . ? C6 C1 C2 119.64(14) . . ? C1 C2 C3 120.16(15) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.80(15) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.61(14) . . ? C3 C4 O2 118.92(14) . . ? C5 C4 O2 120.37(15) . . ? C4 C5 C6 119.59(15) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C1 C6 C5 120.18(15) . . ? C1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O2 C7 C12 123.62(13) . . ? O2 C7 C8 115.94(14) . . ? C12 C7 C8 120.42(14) . . ? C9 C8 C7 119.59(16) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 119.33(14) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C9 C10 C11 121.89(15) . . ? C9 C10 N1 119.05(14) . . ? C11 C10 N1 119.06(16) . . ? C12 C11 C10 118.68(15) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C7 120.03(14) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.163 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.030 # END# data_3 _database_code_depnum_ccdc_archive 'CCDC 264998' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(4-methoxyphenoxy)-4-nitrobenzene ; _chemical_name_common 1-(4-methoxyphenoxy)-4-nitrobenzene _chemical_melting_point 383 _chemical_formula_moiety 'C13 H11 N O4' _chemical_formula_sum 'C13 H11 N O4' _chemical_formula_weight 245.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3992(3) _cell_length_b 7.4839(2) _cell_length_c 12.2812(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.4310(10) _cell_angle_gamma 90.00 _cell_volume 1117.02(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2981 _cell_measurement_theta_min 3.196 _cell_measurement_theta_max 27.490 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart 6K' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8309 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2565 _reflns_number_gt 2039 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker smart' _computing_cell_refinement 'Bruker saint' _computing_data_reduction 'Bruker saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.0960P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2565 _refine_ls_number_parameters 207 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.01393(8) 0.22608(15) 0.35420(9) 0.0279(3) Uani 1 1 d . . . C1 C 0.92113(9) 0.16787(16) 0.40199(10) 0.0230(3) Uani 1 1 d . . . O1 O 1.08658(8) 0.31626(15) 0.41131(8) 0.0396(3) Uani 1 1 d . . . O2 O 1.01629(7) 0.18170(16) 0.25827(7) 0.0380(3) Uani 1 1 d . . . C2 C 0.83897(10) 0.06536(17) 0.33771(10) 0.0243(3) Uani 1 1 d . . . O3 O 0.65769(7) -0.00619(12) 0.53005(7) 0.0252(2) Uani 1 1 d . . . C3 C 0.75120(10) 0.01101(16) 0.38321(10) 0.0236(3) Uani 1 1 d . . . O4 O 0.60078(7) 0.09059(11) 0.96177(7) 0.0244(2) Uani 1 1 d . . . C4 C 0.74802(9) 0.05546(15) 0.49314(10) 0.0215(3) Uani 1 1 d . . . C5 C 0.83136(10) 0.15673(16) 0.55677(10) 0.0237(3) Uani 1 1 d . . . C6 C 0.91859(10) 0.21456(17) 0.51048(10) 0.0247(3) Uani 1 1 d . . . C7 C 0.65040(10) 0.02168(16) 0.64146(10) 0.0220(3) Uani 1 1 d . . . C8 C 0.71832(10) -0.06947(17) 0.72613(10) 0.0244(3) Uani 1 1 d . . . C9 C 0.70483(10) -0.04818(16) 0.83532(10) 0.0232(3) Uani 1 1 d . . . C10 C 0.62167(9) 0.06265(15) 0.85800(9) 0.0210(3) Uani 1 1 d . . . C11 C 0.55388(10) 0.15424(16) 0.77150(10) 0.0231(3) Uani 1 1 d . . . C12 C 0.56786(10) 0.13380(16) 0.66314(10) 0.0234(3) Uani 1 1 d . . . C13 C 0.65644(11) -0.02254(18) 1.04863(10) 0.0259(3) Uani 1 1 d . . . H6 H 0.9749(12) 0.285(2) 0.5514(12) 0.031(4) Uiso 1 1 d . . . H13C H 0.6264(12) 0.010(2) 1.1144(13) 0.033(4) Uiso 1 1 d . . . H8 H 0.7758(11) -0.148(2) 0.7085(11) 0.026(3) Uiso 1 1 d . . . H2 H 0.8428(11) 0.033(2) 0.2632(13) 0.032(4) Uiso 1 1 d . . . H13B H 0.6396(11) -0.150(2) 1.0303(12) 0.029(4) Uiso 1 1 d . . . H13A H 0.7346(12) -0.001(2) 1.0609(12) 0.030(4) Uiso 1 1 d . . . H5 H 0.8289(11) 0.1862(19) 0.6311(12) 0.026(3) Uiso 1 1 d . . . H12 H 0.5209(12) 0.196(2) 0.6027(12) 0.030(4) Uiso 1 1 d . . . H11 H 0.4976(11) 0.2332(18) 0.7892(11) 0.023(3) Uiso 1 1 d . . . H3 H 0.6921(11) -0.0568(19) 0.3405(11) 0.025(3) Uiso 1 1 d . . . H9 H 0.7532(12) -0.1088(19) 0.8926(12) 0.027(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0219(5) 0.0366(6) 0.0254(5) 0.0058(5) 0.0049(4) 0.0021(4) C1 0.0202(5) 0.0259(6) 0.0234(6) 0.0051(5) 0.0056(5) 0.0025(5) O1 0.0282(5) 0.0534(6) 0.0374(5) -0.0011(5) 0.0073(4) -0.0124(4) O2 0.0286(5) 0.0647(7) 0.0221(5) 0.0045(4) 0.0083(4) 0.0006(5) C2 0.0268(6) 0.0266(6) 0.0194(6) -0.0002(5) 0.0044(5) 0.0036(5) O3 0.0250(4) 0.0306(5) 0.0207(4) -0.0029(3) 0.0067(3) -0.0069(4) C3 0.0245(6) 0.0236(6) 0.0220(6) -0.0012(5) 0.0027(5) -0.0006(5) O4 0.0260(4) 0.0264(5) 0.0215(4) 0.0018(3) 0.0066(3) 0.0040(3) C4 0.0208(6) 0.0203(5) 0.0240(6) 0.0020(4) 0.0057(5) 0.0013(4) C5 0.0260(6) 0.0247(6) 0.0206(6) -0.0024(5) 0.0049(5) -0.0001(5) C6 0.0223(6) 0.0262(6) 0.0248(6) 0.0002(5) 0.0027(5) -0.0013(5) C7 0.0228(6) 0.0234(6) 0.0207(5) -0.0011(5) 0.0065(5) -0.0051(5) C8 0.0219(6) 0.0244(6) 0.0278(6) -0.0013(5) 0.0070(5) 0.0003(5) C9 0.0211(6) 0.0239(6) 0.0240(6) 0.0021(5) 0.0031(5) 0.0013(5) C10 0.0215(5) 0.0204(5) 0.0220(5) -0.0008(4) 0.0061(4) -0.0040(4) C11 0.0210(5) 0.0224(6) 0.0266(6) 0.0012(5) 0.0061(5) 0.0005(5) C12 0.0213(5) 0.0236(6) 0.0244(6) 0.0039(5) 0.0026(5) -0.0015(5) C13 0.0277(7) 0.0282(7) 0.0217(6) 0.0024(5) 0.0041(5) 0.0022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 O1 1.2281(14) . ? N1 O2 1.2301(13) . ? N1 C1 1.4580(15) . ? C1 C6 1.3838(17) . ? C1 C2 1.3895(17) . ? C2 C3 1.3795(17) . ? C2 H2 0.957(15) . ? O3 C4 1.3690(14) . ? O3 C7 1.4045(13) . ? C3 C4 1.3986(16) . ? C3 H3 0.957(14) . ? O4 C10 1.3659(14) . ? O4 C13 1.4281(14) . ? C4 C5 1.3903(17) . ? C5 C6 1.3872(17) . ? C5 H5 0.945(14) . ? C6 H6 0.938(15) . ? C7 C8 1.3817(17) . ? C7 C12 1.3894(17) . ? C8 C9 1.3930(17) . ? C8 H8 0.980(14) . ? C9 C10 1.3937(17) . ? C9 H9 0.946(15) . ? C10 C11 1.3968(17) . ? C11 C12 1.3841(17) . ? C11 H11 0.971(14) . ? C12 H12 0.965(15) . ? C13 H13C 0.985(16) . ? C13 H13B 0.993(16) . ? C13 H13A 0.964(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 N1 O2 122.78(11) . . ? O1 N1 C1 118.84(10) . . ? O2 N1 C1 118.38(10) . . ? C6 C1 C2 122.17(11) . . ? C6 C1 N1 118.84(11) . . ? C2 C1 N1 118.98(11) . . ? C3 C2 C1 118.76(11) . . ? C3 C2 H2 120.3(9) . . ? C1 C2 H2 120.9(9) . . ? C4 O3 C7 119.17(9) . . ? C2 C3 C4 119.75(11) . . ? C2 C3 H3 120.9(8) . . ? C4 C3 H3 119.3(8) . . ? C10 O4 C13 116.95(9) . . ? O3 C4 C5 124.28(11) . . ? O3 C4 C3 114.89(10) . . ? C5 C4 C3 120.82(11) . . ? C6 C5 C4 119.52(11) . . ? C6 C5 H5 120.0(8) . . ? C4 C5 H5 120.5(8) . . ? C1 C6 C5 118.96(11) . . ? C1 C6 H6 120.1(9) . . ? C5 C6 H6 120.9(9) . . ? C8 C7 C12 121.07(11) . . ? C8 C7 O3 120.84(11) . . ? C12 C7 O3 117.94(10) . . ? C7 C8 C9 119.77(11) . . ? C7 C8 H8 119.3(8) . . ? C9 C8 H8 120.9(8) . . ? C8 C9 C10 119.69(11) . . ? C8 C9 H9 118.8(9) . . ? C10 C9 H9 121.5(9) . . ? O4 C10 C9 124.21(11) . . ? O4 C10 C11 115.96(10) . . ? C9 C10 C11 119.84(11) . . ? C12 C11 C10 120.39(11) . . ? C12 C11 H11 121.0(8) . . ? C10 C11 H11 118.6(8) . . ? C11 C12 C7 119.24(11) . . ? C11 C12 H12 121.0(8) . . ? C7 C12 H12 119.8(8) . . ? O4 C13 H13C 105.2(9) . . ? O4 C13 H13B 110.6(8) . . ? H13C C13 H13B 108.9(12) . . ? O4 C13 H13A 109.7(9) . . ? H13C C13 H13A 111.2(12) . . ? H13B C13 H13A 111.0(12) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 C1 C6 -0.68(17) . . . . ? O2 N1 C1 C6 178.94(11) . . . . ? O1 N1 C1 C2 -179.80(11) . . . . ? O2 N1 C1 C2 -0.18(17) . . . . ? C6 C1 C2 C3 1.08(18) . . . . ? N1 C1 C2 C3 -179.84(11) . . . . ? C1 C2 C3 C4 -1.74(18) . . . . ? C7 O3 C4 C5 -4.82(17) . . . . ? C7 O3 C4 C3 175.96(10) . . . . ? C2 C3 C4 O3 -179.57(10) . . . . ? C2 C3 C4 C5 1.18(18) . . . . ? O3 C4 C5 C6 -179.07(11) . . . . ? C3 C4 C5 C6 0.11(18) . . . . ? C2 C1 C6 C5 0.20(18) . . . . ? N1 C1 C6 C5 -178.89(11) . . . . ? C4 C5 C6 C1 -0.78(18) . . . . ? C4 O3 C7 C8 -70.45(14) . . . . ? C4 O3 C7 C12 113.99(12) . . . . ? C12 C7 C8 C9 -0.49(18) . . . . ? O3 C7 C8 C9 -175.91(10) . . . . ? C7 C8 C9 C10 1.07(18) . . . . ? C13 O4 C10 C9 -10.22(16) . . . . ? C13 O4 C10 C11 170.13(10) . . . . ? C8 C9 C10 O4 179.12(11) . . . . ? C8 C9 C10 C11 -1.24(17) . . . . ? O4 C10 C11 C12 -179.49(10) . . . . ? C9 C10 C11 C12 0.84(18) . . . . ? C10 C11 C12 C7 -0.26(18) . . . . ? C8 C7 C12 C11 0.08(18) . . . . ? O3 C7 C12 C11 175.63(10) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.271 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.044 # END# data_4 _database_code_depnum_ccdc_archive 'CCDC 264999' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Iodo-4'-nitrodiphenyl ether ; _chemical_name_common "4-Iodo-4'-nitrodiphenyl ether" _chemical_melting_point 338 _chemical_formula_moiety 'C12 H8 I N O3' _chemical_formula_sum 'C12 H8 I N O3' _chemical_formula_weight 341.09 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 9.547(14) _cell_length_b 28.28(4) _cell_length_c 10.080(14) _cell_angle_alpha 90.00 _cell_angle_beta 117.06(2) _cell_angle_gamma 90.00 _cell_volume 2424(6) _cell_formula_units_Z 8 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used 6405 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 26.04 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 2.637 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 243(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5672 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2957 _reflns_number_gt 2198 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1788P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2957 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0885 _refine_ls_wR_factor_ref 0.2453 _refine_ls_wR_factor_gt 0.2242 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.33243(12) 0.04862(3) 0.81114(10) 0.0500(5) Uani 1 1 d . . . O1 O 0.6314(12) 0.2497(3) 0.9257(13) 0.061(3) Uani 1 1 d . . . N1 N 0.3237(17) 0.4228(6) 0.7987(15) 0.052(4) Uani 1 1 d . . . C1 C 0.5496(16) 0.2902(5) 0.8954(15) 0.042(3) Uani 1 1 d . . . I2 I -0.00474(15) 0.77429(4) 0.18800(14) 0.0727(5) Uani 1 1 d . . . O2 O 0.2052(19) 0.4267(4) 0.6924(16) 0.082(4) Uani 1 1 d . . . N2 N 0.4527(15) 0.4151(6) 0.4376(17) 0.059(4) Uani 1 1 d . . . C2 C 0.4087(18) 0.2965(5) 0.7694(15) 0.051(3) Uani 1 1 d . . . H2 H 0.3627 0.2711 0.7037 0.061 Uiso 1 1 d R . . O3 O 0.3922(18) 0.4538(4) 0.8874(18) 0.084(4) Uani 1 1 d . . . C3 C 0.3335(19) 0.3412(5) 0.7374(16) 0.051(3) Uani 1 1 d . . . H3 H 0.2382 0.3456 0.6507 0.061 Uiso 1 1 d R . . O4 O 0.0745(15) 0.5648(4) 0.0641(11) 0.071(3) Uani 1 1 d . . . C4 C 0.3993(16) 0.3769(5) 0.8328(14) 0.038(3) Uani 1 1 d . . . O5 O 0.5009(19) 0.3950(5) 0.3889(19) 0.093(5) Uani 1 1 d . . . C5 C 0.5426(18) 0.3701(5) 0.9584(14) 0.045(4) Uani 1 1 d . . . H5 H 0.5905 0.3957 1.0229 0.054 Uiso 1 1 d R . . O6 O 0.4591(16) 0.4190(5) 0.5615(17) 0.088(4) Uani 1 1 d . . . C6 C 0.6152(17) 0.3271(5) 0.9896(15) 0.046(4) Uani 1 1 d . . . H6 H 0.7107 0.3230 1.0764 0.056 Uiso 1 1 d R . . C7 C 0.5526(16) 0.2065(5) 0.8928(14) 0.047(4) Uani 1 1 d . . . C8 C 0.5931(19) 0.1733(6) 0.8145(17) 0.055(4) Uani 1 1 d . . . H8 H 0.6626 0.1814 0.7756 0.066 Uiso 1 1 d R . . C9 C 0.5324(18) 0.1293(5) 0.7945(14) 0.049(4) Uani 1 1 d . . . H9 H 0.5619 0.1066 0.7437 0.059 Uiso 1 1 d R . . C10 C 0.4273(15) 0.1173(5) 0.8481(13) 0.037(3) Uani 1 1 d . . . C11 C 0.3805(17) 0.1502(4) 0.9196(14) 0.041(3) Uani 1 1 d . . . H11 H 0.3062 0.1423 0.9530 0.049 Uiso 1 1 d R . . C12 C 0.4425(16) 0.1945(5) 0.9411(15) 0.044(4) Uani 1 1 d . . . H12 H 0.4104 0.2172 0.9895 0.053 Uiso 1 1 d R . . C13 C 0.1727(19) 0.5308(5) 0.1609(14) 0.050(4) Uani 1 1 d . . . C14 C 0.266(2) 0.5050(6) 0.1196(17) 0.062(5) Uani 1 1 d . . . H14 H 0.2665 0.5116 0.0283 0.074 Uiso 1 1 d R . . C15 C 0.3564(17) 0.4708(6) 0.2041(16) 0.049(4) Uani 1 1 d . . . H15 H 0.4202 0.4531 0.1740 0.058 Uiso 1 1 d R . . C16 C 0.3548(17) 0.4613(5) 0.3438(18) 0.052(4) Uani 1 1 d . . . C17 C 0.261(2) 0.4877(6) 0.3824(18) 0.060(5) Uani 1 1 d . . . H17 H 0.2579 0.4812 0.4726 0.072 Uiso 1 1 d R . . C18 C 0.170(2) 0.5238(5) 0.2934(17) 0.057(4) Uani 1 1 d . . . H18 H 0.1081 0.5427 0.3228 0.068 Uiso 1 1 d R . . C19 C 0.058(2) 0.6096(6) 0.1101(16) 0.052(4) Uani 1 1 d . . . C20 C 0.1838(19) 0.6330(5) 0.2084(15) 0.047(4) Uani 1 1 d . . . H20 H 0.2814 0.6177 0.2591 0.056 Uiso 1 1 d R . . C21 C 0.1679(17) 0.6808(6) 0.2348(15) 0.050(4) Uani 1 1 d . . . H21 H 0.2555 0.6980 0.3023 0.060 Uiso 1 1 d R . . C22 C 0.0211(18) 0.7027(5) 0.1602(15) 0.045(4) Uani 1 1 d . . . C23 C -0.1036(18) 0.6766(5) 0.0627(15) 0.047(4) Uani 1 1 d . . . H23 H -0.2027 0.6911 0.0120 0.056 Uiso 1 1 d R . . C24 C -0.0880(18) 0.6303(6) 0.0375(15) 0.048(4) Uani 1 1 d . . . H24 H -0.1754 0.6126 -0.0286 0.058 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0841(8) 0.0249(7) 0.0503(7) 0.0026(4) 0.0387(6) -0.0027(5) O1 0.065(7) 0.003(6) 0.100(9) 0.002(5) 0.024(6) 0.001(5) N1 0.067(9) 0.065(12) 0.031(7) -0.014(8) 0.028(7) -0.007(8) C1 0.056(9) 0.017(9) 0.051(8) -0.013(7) 0.023(7) -0.011(7) I2 0.0884(10) 0.0424(9) 0.0838(9) -0.0020(6) 0.0362(7) 0.0088(6) O2 0.121(11) 0.048(9) 0.075(9) 0.014(7) 0.044(9) 0.026(8) N2 0.031(7) 0.085(14) 0.058(10) -0.009(9) 0.017(7) -0.029(8) C2 0.077(8) 0.022(6) 0.043(6) -0.014(5) 0.018(6) -0.008(5) O3 0.125(11) 0.028(8) 0.111(11) 0.010(7) 0.065(10) 0.018(7) C3 0.077(8) 0.022(6) 0.043(6) -0.014(5) 0.018(6) -0.008(5) O4 0.123(10) 0.039(7) 0.044(6) -0.005(6) 0.031(6) 0.019(6) C4 0.068(9) 0.021(9) 0.037(8) 0.003(7) 0.034(7) 0.002(7) O5 0.118(13) 0.055(10) 0.108(12) 0.045(9) 0.052(10) 0.021(8) C5 0.095(11) 0.015(9) 0.034(8) -0.009(6) 0.035(8) -0.009(8) O6 0.114(11) 0.055(9) 0.101(11) 0.029(8) 0.053(9) 0.017(7) C6 0.065(10) 0.022(10) 0.042(8) 0.022(7) 0.014(7) 0.011(7) C7 0.053(9) 0.031(10) 0.034(7) 0.002(7) 0.000(7) -0.005(7) C8 0.091(12) 0.035(11) 0.072(10) -0.005(8) 0.065(10) -0.010(8) C9 0.088(11) 0.026(10) 0.046(8) -0.008(7) 0.041(8) -0.003(8) C10 0.060(9) 0.033(9) 0.029(7) -0.001(6) 0.029(7) -0.001(7) C11 0.081(10) 0.015(8) 0.044(8) 0.005(6) 0.044(8) 0.001(7) C12 0.059(9) 0.029(10) 0.060(9) -0.001(7) 0.039(8) 0.006(7) C13 0.088(11) 0.034(10) 0.029(7) 0.009(7) 0.029(8) 0.006(8) C14 0.106(14) 0.057(12) 0.051(9) -0.005(9) 0.060(10) -0.010(11) C15 0.060(10) 0.042(10) 0.057(9) -0.007(8) 0.037(8) 0.006(8) C16 0.053(9) 0.032(9) 0.074(11) 0.009(8) 0.031(8) 0.000(7) C17 0.095(12) 0.047(11) 0.074(10) 0.001(9) 0.071(10) -0.007(9) C18 0.095(12) 0.023(10) 0.066(10) 0.009(8) 0.047(9) 0.020(8) C19 0.090(12) 0.046(11) 0.035(8) 0.001(8) 0.040(9) 0.002(9) C20 0.083(11) 0.028(10) 0.040(8) -0.002(7) 0.037(8) 0.009(8) C21 0.052(9) 0.061(12) 0.040(8) 0.009(8) 0.024(7) 0.008(8) C22 0.077(11) 0.034(9) 0.035(7) 0.008(7) 0.035(8) 0.007(8) C23 0.064(10) 0.035(10) 0.043(8) -0.006(7) 0.025(8) 0.015(8) C24 0.062(10) 0.044(11) 0.034(7) 0.000(7) 0.019(7) -0.005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C10 2.104(14) . ? O1 C1 1.341(17) . ? O1 C7 1.393(18) . ? N1 O2 1.157(15) . ? N1 O3 1.210(17) . ? N1 C4 1.45(2) . ? C1 C6 1.357(19) . ? C1 C2 1.379(19) . ? I2 C22 2.074(15) . ? N2 O5 0.991(18) . ? N2 O6 1.227(18) . ? N2 C16 1.63(2) . ? C2 C3 1.42(2) . ? C3 C4 1.337(19) . ? O4 C19 1.380(19) . ? O4 C13 1.388(18) . ? C4 C5 1.391(19) . ? C5 C6 1.36(2) . ? C7 C12 1.387(19) . ? C7 C8 1.39(2) . ? C8 C9 1.35(2) . ? C9 C10 1.380(18) . ? C10 C11 1.372(17) . ? C11 C12 1.359(19) . ? C13 C14 1.36(2) . ? C13 C18 1.363(19) . ? C14 C15 1.32(2) . ? C15 C16 1.44(2) . ? C16 C17 1.35(2) . ? C17 C18 1.37(2) . ? C19 C20 1.33(2) . ? C19 C24 1.38(2) . ? C20 C21 1.40(2) . ? C21 C22 1.40(2) . ? C22 C23 1.36(2) . ? C23 C24 1.36(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C7 119.9(11) . . ? O2 N1 O3 125.9(17) . . ? O2 N1 C4 118.6(14) . . ? O3 N1 C4 115.5(14) . . ? O1 C1 C6 117.5(13) . . ? O1 C1 C2 122.9(13) . . ? C6 C1 C2 119.5(14) . . ? O5 N2 O6 137(2) . . ? O5 N2 C16 116.4(16) . . ? O6 N2 C16 105.6(15) . . ? C1 C2 C3 120.4(13) . . ? C4 C3 C2 119.1(14) . . ? C19 O4 C13 122.9(11) . . ? C3 C4 C5 119.8(13) . . ? C3 C4 N1 119.0(13) . . ? C5 C4 N1 121.1(13) . . ? C6 C5 C4 121.2(13) . . ? C1 C6 C5 120.0(13) . . ? C12 C7 C8 118.9(14) . . ? C12 C7 O1 123.1(13) . . ? C8 C7 O1 117.9(13) . . ? C9 C8 C7 119.8(13) . . ? C8 C9 C10 120.5(13) . . ? C11 C10 C9 120.6(13) . . ? C11 C10 I1 120.2(9) . . ? C9 C10 I1 119.2(10) . . ? C12 C11 C10 119.1(12) . . ? C11 C12 C7 121.0(13) . . ? C14 C13 C18 122.1(15) . . ? C14 C13 O4 119.0(12) . . ? C18 C13 O4 118.8(13) . . ? C15 C14 C13 121.5(13) . . ? C14 C15 C16 118.4(12) . . ? C17 C16 C15 118.8(14) . . ? C17 C16 N2 123.6(14) . . ? C15 C16 N2 117.2(13) . . ? C16 C17 C18 121.7(14) . . ? C13 C18 C17 117.4(14) . . ? C20 C19 C24 122.3(15) . . ? C20 C19 O4 120.3(15) . . ? C24 C19 O4 116.9(15) . . ? C19 C20 C21 118.8(15) . . ? C22 C21 C20 119.7(15) . . ? C23 C22 C21 118.7(14) . . ? C23 C22 I2 120.4(11) . . ? C21 C22 I2 120.8(12) . . ? C24 C23 C22 121.5(14) . . ? C23 C24 C19 118.9(14) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C6 146.0(13) . . . . ? C7 O1 C1 C2 -38(2) . . . . ? O1 C1 C2 C3 -175.1(13) . . . . ? C6 C1 C2 C3 1(2) . . . . ? C1 C2 C3 C4 -1(2) . . . . ? C2 C3 C4 C5 2(2) . . . . ? C2 C3 C4 N1 179.0(12) . . . . ? O2 N1 C4 C3 2.9(19) . . . . ? O3 N1 C4 C3 -177.7(13) . . . . ? O2 N1 C4 C5 179.4(13) . . . . ? O3 N1 C4 C5 -1.2(18) . . . . ? C3 C4 C5 C6 -2(2) . . . . ? N1 C4 C5 C6 -179.0(12) . . . . ? O1 C1 C6 C5 175.3(12) . . . . ? C2 C1 C6 C5 -1(2) . . . . ? C4 C5 C6 C1 2(2) . . . . ? C1 O1 C7 C12 -52.9(19) . . . . ? C1 O1 C7 C8 130.6(15) . . . . ? C12 C7 C8 C9 -4(2) . . . . ? O1 C7 C8 C9 172.8(13) . . . . ? C7 C8 C9 C10 2(2) . . . . ? C8 C9 C10 C11 1(2) . . . . ? C8 C9 C10 I1 178.9(12) . . . . ? C9 C10 C11 C12 -2(2) . . . . ? I1 C10 C11 C12 -179.4(10) . . . . ? C10 C11 C12 C7 -1(2) . . . . ? C8 C7 C12 C11 3(2) . . . . ? O1 C7 C12 C11 -173.1(13) . . . . ? C19 O4 C13 C14 -135.3(16) . . . . ? C19 O4 C13 C18 46(2) . . . . ? C18 C13 C14 C15 2(3) . . . . ? O4 C13 C14 C15 -176.9(15) . . . . ? C13 C14 C15 C16 0(2) . . . . ? C14 C15 C16 C17 0(2) . . . . ? C14 C15 C16 N2 173.5(14) . . . . ? O5 N2 C16 C17 168.6(19) . . . . ? O6 N2 C16 C17 -19(2) . . . . ? O5 N2 C16 C15 -4(2) . . . . ? O6 N2 C16 C15 167.9(14) . . . . ? C15 C16 C17 C18 -1(2) . . . . ? N2 C16 C17 C18 -174.3(14) . . . . ? C14 C13 C18 C17 -3(3) . . . . ? O4 C13 C18 C17 175.8(15) . . . . ? C16 C17 C18 C13 3(3) . . . . ? C13 O4 C19 C20 41(2) . . . . ? C13 O4 C19 C24 -145.9(14) . . . . ? C24 C19 C20 C21 -2(2) . . . . ? O4 C19 C20 C21 169.9(12) . . . . ? C19 C20 C21 C22 1.1(19) . . . . ? C20 C21 C22 C23 -0.1(19) . . . . ? C20 C21 C22 I2 -176.7(9) . . . . ? C21 C22 C23 C24 0(2) . . . . ? I2 C22 C23 C24 176.9(10) . . . . ? C22 C23 C24 C19 -1(2) . . . . ? C20 C19 C24 C23 2(2) . . . . ? O4 C19 C24 C23 -170.0(12) . . . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 2.683 _refine_diff_density_min -1.707 _refine_diff_density_rms 0.252 # END# data_5 _database_code_depnum_ccdc_archive 'CCDC 265000' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Chloro-4'-nitrodiphenyl ether ; _chemical_name_common "4-Chloro-4'-nitrodiphenyl ether" _chemical_melting_point 248 _chemical_formula_moiety 'C12 H8 Cl N O3' _chemical_formula_sum 'C12 H8 Cl N O3' _chemical_formula_weight 249.64 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/m' _symmetry_space_group_name_Hall '-P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 10.0600(6) _cell_length_b 7.2712(5) _cell_length_c 15.6390(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.4580(10) _cell_angle_gamma 90.00 _cell_volume 1134.29(13) _cell_formula_units_Z 4 _cell_measurement_temperature 243(2) _cell_measurement_reflns_used 4756 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 27.01 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.462 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 243(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14588 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.26 _reflns_number_total 3033 _reflns_number_gt 2467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0941P)^2^+0.1463P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3033 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.94654(6) 0.2500 0.88644(4) 0.0606(2) Uani 1 2 d S . . N1 N 1.6698(2) 0.2500 1.41169(13) 0.0581(5) Uani 1 2 d S . . O1 O 1.49897(16) 0.2500 1.06012(10) 0.0621(5) Uani 1 2 d S . . O2 O 1.5881(2) 0.2500 1.46226(13) 0.1057(9) Uani 1 2 d S . . O3 O 1.79028(19) 0.2500 1.43484(12) 0.0700(5) Uani 1 2 d S . . C1 C 1.5327(2) 0.2500 1.14721(14) 0.0474(5) Uani 1 2 d S . . C2 C 1.4403(2) 0.2500 1.20510(15) 0.0573(6) Uani 1 2 d S . . H2 H 1.3480 0.2500 1.1854 0.069 Uiso 1 2 d SR . . C3 C 1.4855(2) 0.2500 1.29272(15) 0.0591(6) Uani 1 2 d S . . H3 H 1.4239 0.2500 1.3331 0.071 Uiso 1 2 d SR . . C4 C 1.6220(2) 0.2500 1.32029(14) 0.0475(5) Uani 1 2 d S . . C5 C 1.7142(2) 0.2500 1.26240(14) 0.0497(5) Uani 1 2 d S . . H5 H 1.8066 0.2500 1.2820 0.060 Uiso 1 2 d SR . . C6 C 1.6694(2) 0.2500 1.17562(15) 0.0539(5) Uani 1 2 d S . . H6 H 1.7312 0.2500 1.1354 0.065 Uiso 1 2 d SR . . C7 C 1.3638(2) 0.2500 1.02487(13) 0.0502(5) Uani 1 2 d S . . C8 C 1.30104(17) 0.0853(3) 1.00519(11) 0.0578(4) Uani 1 1 d . . . H8 H 1.3455 -0.0262 1.0199 0.069 Uiso 1 1 d R . . C9 C 1.17114(17) 0.0855(2) 0.96321(11) 0.0561(4) Uani 1 1 d . . . H9 H 1.1263 -0.0263 0.9497 0.067 Uiso 1 1 d R . . C10 C 1.1081(2) 0.2500 0.94154(13) 0.0472(5) Uani 1 2 d S . . Cl2 Cl 0.07576(6) 0.2500 0.17139(4) 0.0629(2) Uani 1 2 d S . . N2 N 0.5706(2) 0.2500 0.78696(14) 0.0618(5) Uani 1 2 d S . . O4 O 0.11205(17) 0.2500 0.54765(11) 0.0742(6) Uani 1 2 d S . . O5 O 0.6797(2) 0.2500 0.76211(14) 0.0962(8) Uani 1 2 d S . . O6 O 0.5552(2) 0.2500 0.86360(11) 0.0776(6) Uani 1 2 d S . . C11 C 0.2292(2) 0.2500 0.60318(15) 0.0546(6) Uani 1 2 d S . . C12 C 0.2150(3) 0.2500 0.69028(16) 0.0592(6) Uani 1 2 d S . . H12 H 0.1290 0.2500 0.7076 0.071 Uiso 1 2 d SR . . C13 C 0.3266(3) 0.2500 0.75106(15) 0.0561(6) Uani 1 2 d S . . H13 H 0.3179 0.2500 0.8102 0.067 Uiso 1 2 d SR . . C14 C 0.4515(2) 0.2500 0.72372(14) 0.0510(5) Uani 1 2 d S . . C15 C 0.4669(2) 0.2500 0.63744(15) 0.0609(6) Uani 1 2 d S . . H15 H 0.5530 0.2500 0.6201 0.073 Uiso 1 2 d SR . . C16 C 0.3546(2) 0.2500 0.57678(15) 0.0591(6) Uani 1 2 d S . . H16 H 0.3635 0.2500 0.5177 0.071 Uiso 1 2 d SR . . C17 C 0.1171(2) 0.2500 0.45911(16) 0.0586(6) Uani 1 2 d S . . C18 C 0.11411(19) 0.0855(3) 0.41601(12) 0.0646(5) Uani 1 1 d . . . H18 H 0.1194 -0.0260 0.4467 0.077 Uiso 1 1 d R . . C19 C 0.10340(18) 0.0855(3) 0.32718(12) 0.0606(4) Uani 1 1 d . . . H19 H 0.1009 -0.0260 0.2966 0.073 Uiso 1 1 d R . . C20 C 0.0963(2) 0.2500 0.28389(14) 0.0491(5) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0480(3) 0.0676(4) 0.0618(4) 0.000 -0.0092(3) 0.000 N1 0.0529(11) 0.0752(13) 0.0441(10) 0.000 -0.0021(8) 0.000 O1 0.0410(8) 0.1041(14) 0.0399(8) 0.000 0.0003(6) 0.000 O2 0.0673(13) 0.207(3) 0.0424(10) 0.000 0.0065(9) 0.000 O3 0.0536(10) 0.0946(14) 0.0560(10) 0.000 -0.0142(8) 0.000 C1 0.0401(10) 0.0604(12) 0.0400(10) 0.000 -0.0011(8) 0.000 C2 0.0370(10) 0.0905(18) 0.0431(11) 0.000 0.0000(9) 0.000 C3 0.0416(11) 0.0940(18) 0.0421(11) 0.000 0.0071(9) 0.000 C4 0.0427(11) 0.0569(12) 0.0408(11) 0.000 -0.0021(8) 0.000 C5 0.0354(9) 0.0608(13) 0.0509(12) 0.000 -0.0016(8) 0.000 C6 0.0385(10) 0.0763(15) 0.0469(12) 0.000 0.0053(9) 0.000 C7 0.0426(10) 0.0727(14) 0.0345(10) 0.000 0.0014(8) 0.000 C8 0.0536(9) 0.0601(10) 0.0572(9) 0.0054(8) -0.0019(7) 0.0072(7) C9 0.0542(9) 0.0516(9) 0.0594(9) -0.0018(7) -0.0036(7) -0.0013(7) C10 0.0445(10) 0.0559(12) 0.0394(10) 0.000 -0.0020(8) 0.000 Cl2 0.0508(3) 0.0862(5) 0.0482(3) 0.000 -0.0065(2) 0.000 N2 0.0663(14) 0.0646(13) 0.0497(12) 0.000 -0.0100(10) 0.000 O4 0.0419(8) 0.1328(18) 0.0468(9) 0.000 0.0018(7) 0.000 O5 0.0563(12) 0.159(2) 0.0670(13) 0.000 -0.0155(10) 0.000 O6 0.0959(15) 0.0894(14) 0.0418(9) 0.000 -0.0129(9) 0.000 C11 0.0433(11) 0.0724(15) 0.0467(12) 0.000 0.0002(9) 0.000 C12 0.0507(12) 0.0789(17) 0.0486(12) 0.000 0.0093(10) 0.000 C13 0.0666(14) 0.0611(13) 0.0410(11) 0.000 0.0081(10) 0.000 C14 0.0547(12) 0.0548(12) 0.0410(11) 0.000 -0.0037(9) 0.000 C15 0.0451(12) 0.0914(18) 0.0455(12) 0.000 0.0034(10) 0.000 C16 0.0470(12) 0.0898(18) 0.0399(11) 0.000 0.0034(9) 0.000 C17 0.0383(10) 0.0886(18) 0.0472(12) 0.000 -0.0008(9) 0.000 C18 0.0637(10) 0.0688(11) 0.0600(10) 0.0128(9) 0.0036(8) 0.0088(8) C19 0.0620(10) 0.0577(10) 0.0606(10) -0.0026(8) 0.0020(8) 0.0032(8) C20 0.0346(9) 0.0621(13) 0.0481(12) 0.000 -0.0042(8) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C10 1.738(2) . ? N1 O2 1.212(3) . ? N1 O3 1.220(3) . ? N1 C4 1.448(3) . ? O1 C1 1.360(3) . ? O1 C7 1.400(3) . ? C1 C2 1.379(3) . ? C1 C6 1.389(3) . ? C2 C3 1.387(3) . ? C3 C4 1.385(3) . ? C4 C5 1.378(3) . ? C5 C6 1.373(3) . ? C7 C8 1.370(2) . ? C7 C8 1.370(2) 4_565 ? C8 C9 1.384(2) . ? C9 C10 1.376(2) . ? C10 C9 1.376(2) 4_565 ? Cl2 C20 1.745(2) . ? N2 O5 1.211(3) . ? N2 O6 1.228(3) . ? N2 C14 1.451(3) . ? O4 C11 1.370(3) . ? O4 C17 1.392(3) . ? C11 C16 1.378(3) . ? C11 C12 1.388(3) . ? C12 C13 1.374(4) . ? C13 C14 1.379(3) . ? C14 C15 1.378(3) . ? C15 C16 1.378(3) . ? C17 C18 1.371(2) 4_565 ? C17 C18 1.371(2) . ? C18 C19 1.379(2) . ? C19 C20 1.372(2) . ? C20 C19 1.372(2) 4_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 N1 O3 122.6(2) . . ? O2 N1 C4 118.6(2) . . ? O3 N1 C4 118.9(2) . . ? C1 O1 C7 119.86(17) . . ? O1 C1 C2 123.74(19) . . ? O1 C1 C6 115.36(19) . . ? C2 C1 C6 120.9(2) . . ? C1 C2 C3 119.1(2) . . ? C4 C3 C2 119.5(2) . . ? C5 C4 C3 121.4(2) . . ? C5 C4 N1 118.9(2) . . ? C3 C4 N1 119.7(2) . . ? C6 C5 C4 119.1(2) . . ? C5 C6 C1 120.0(2) . . ? C8 C7 C8 121.9(2) . 4_565 ? C8 C7 O1 118.95(11) . . ? C8 C7 O1 118.95(11) 4_565 . ? C7 C8 C9 118.98(16) . . ? C10 C9 C8 119.64(16) . . ? C9 C10 C9 120.8(2) 4_565 . ? C9 C10 Cl1 119.59(10) 4_565 . ? C9 C10 Cl1 119.59(10) . . ? O5 N2 O6 123.2(2) . . ? O5 N2 C14 118.9(2) . . ? O6 N2 C14 117.8(2) . . ? C11 O4 C17 119.39(18) . . ? O4 C11 C16 123.8(2) . . ? O4 C11 C12 115.7(2) . . ? C16 C11 C12 120.6(2) . . ? C13 C12 C11 120.0(2) . . ? C12 C13 C14 118.8(2) . . ? C15 C14 C13 121.8(2) . . ? C15 C14 N2 118.6(2) . . ? C13 C14 N2 119.6(2) . . ? C16 C15 C14 119.2(2) . . ? C11 C16 C15 119.7(2) . . ? C18 C17 C18 121.4(2) 4_565 . ? C18 C17 O4 119.17(12) 4_565 . ? C18 C17 O4 119.17(12) . . ? C17 C18 C19 119.26(18) . . ? C20 C19 C18 119.30(18) . . ? C19 C20 C19 121.4(2) . 4_565 ? C19 C20 Cl2 119.31(11) . . ? C19 C20 Cl2 119.31(11) 4_565 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.553 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.068 # END# data_6 _database_code_depnum_ccdc_archive 'CCDC 265001' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-Bromo-4-(4-nitrophenoxy)benzene ; _chemical_name_common 1-Bromo-4-(4-nitrophenoxy)benzene _chemical_melting_point 347 _chemical_formula_moiety 'C12 H8 Br N O3' _chemical_formula_sum 'C24 H16 Br2 N2 O6' _chemical_formula_weight 588.21 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 9.1199(9) _cell_length_b 27.782(3) _cell_length_c 9.8887(9) _cell_angle_alpha 90.00 _cell_angle_beta 116.7450(10) _cell_angle_gamma 90.00 _cell_volume 2237.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7514 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 26.03 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 3.669 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4159 _exptl_absorpt_correction_T_max 0.6277 _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13585 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 26.05 _reflns_number_total 4417 _reflns_number_gt 3779 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. N1 has refined isotropic thermal parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+5.0975P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4417 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.16302(4) 0.051465(12) 0.68734(4) 0.02091(12) Uani 1 1 d . . . Br2 Br 0.51074(5) 0.775247(14) 0.29224(5) 0.03074(13) Uani 1 1 d . . . O4 O -0.1466(3) 0.24860(8) 0.5776(3) 0.0199(5) Uani 1 1 d . . . C2 C 0.4868(4) 0.70893(13) 0.3288(4) 0.0196(7) Uani 1 1 d . . . O1 O 0.4414(4) 0.56914(10) 0.4417(3) 0.0284(6) Uani 1 1 d . . . O2 O -0.0037(4) 0.39570(10) 0.1121(4) 0.0436(9) Uani 1 1 d . . . C19 C 0.0733(4) 0.11467(12) 0.6575(4) 0.0160(7) Uani 1 1 d . . . C18 C -0.0418(4) 0.12507(13) 0.7085(4) 0.0182(7) Uani 1 1 d . . . H18 H -0.0738 0.1011 0.7582 0.022 Uiso 1 1 calc R . . C8 C 0.2448(4) 0.49046(13) 0.1110(4) 0.0209(8) Uani 1 1 d . . . H8 H 0.2446 0.4839 0.0166 0.025 Uiso 1 1 calc R . . C1 C 0.3361(4) 0.68667(13) 0.2503(4) 0.0203(8) Uani 1 1 d . . . H1 H 0.2456 0.7037 0.1755 0.024 Uiso 1 1 calc R . . C15 C -0.1275(4) 0.32754(13) 0.5038(4) 0.0194(7) Uani 1 1 d . . . H15 H -0.2261 0.3221 0.4139 0.023 Uiso 1 1 calc R . . C3 C 0.6222(4) 0.68449(13) 0.4343(4) 0.0212(8) Uani 1 1 d . . . H3 H 0.7255 0.7001 0.4844 0.025 Uiso 1 1 calc R . . O3 O 0.0369(4) 0.42115(11) -0.0659(3) 0.0354(7) Uani 1 1 d . . . C13 C 0.1608(4) 0.34245(13) 0.7671(4) 0.0205(8) Uani 1 1 d . . . H13 H 0.2595 0.3479 0.8569 0.025 Uiso 1 1 calc R . . C7 C 0.3410(5) 0.52698(13) 0.2030(4) 0.0221(8) Uani 1 1 d . . . H7 H 0.4082 0.5459 0.1729 0.026 Uiso 1 1 calc R . . C11 C -0.0585(4) 0.29109(12) 0.6072(4) 0.0168(7) Uani 1 1 d . . . C10 C 0.2390(5) 0.50915(13) 0.3854(4) 0.0218(8) Uani 1 1 d . . . H10 H 0.2372 0.5161 0.4787 0.026 Uiso 1 1 calc R . . C16 C -0.0614(4) 0.20495(12) 0.6130(4) 0.0166(7) Uani 1 1 d . . . C20 C 0.1230(4) 0.14893(13) 0.5863(4) 0.0183(7) Uani 1 1 d . . . H20 H 0.2029 0.1413 0.5528 0.022 Uiso 1 1 calc R . . C12 C 0.0866(4) 0.29776(13) 0.7393(4) 0.0208(8) Uani 1 1 d . . . H12 H 0.1337 0.2721 0.8090 0.025 Uiso 1 1 calc R . . C14 C -0.0527(4) 0.37236(13) 0.5311(4) 0.0190(7) Uani 1 1 d . . . H14 H -0.0988 0.3979 0.4606 0.023 Uiso 1 1 calc R . . C5 C 0.4532(5) 0.61461(13) 0.3914(4) 0.0204(8) Uani 1 1 d . . . C6 C 0.3381(4) 0.53569(13) 0.3399(4) 0.0213(8) Uani 1 1 d . . . C9 C 0.1487(4) 0.46358(13) 0.1585(4) 0.0189(7) Uani 1 1 d . . . C17 C -0.1100(4) 0.17076(13) 0.6866(4) 0.0192(7) Uani 1 1 d . . . H17 H -0.1887 0.1785 0.7215 0.023 Uiso 1 1 calc R . . C4 C 0.6048(5) 0.63690(13) 0.4657(4) 0.0213(8) Uani 1 1 d . . . H4 H 0.6964 0.6196 0.5379 0.026 Uiso 1 1 calc R . . N2 N 0.1740(3) 0.42841(12) 0.6957(3) 0.0203(7) Uani 1 1 d . . . O5 O 0.1040(4) 0.45854(10) 0.6049(3) 0.0317(7) Uani 1 1 d . . . O6 O 0.3002(3) 0.43091(10) 0.8111(3) 0.0301(6) Uani 1 1 d . . . N1 N 0.0483(4) 0.42121(12) 0.0621(4) 0.0229(7) Uiso 1 1 d . . . C24 C 0.0911(4) 0.37905(12) 0.6638(4) 0.0164(7) Uani 1 1 d . . . C23 C 0.0546(4) 0.19503(13) 0.5638(4) 0.0182(7) Uani 1 1 d . . . H23 H 0.0877 0.2192 0.5152 0.022 Uiso 1 1 calc R . . C21 C 0.1436(5) 0.47271(13) 0.2944(4) 0.0222(8) Uani 1 1 d . . . H21 H 0.0754 0.4541 0.3238 0.027 Uiso 1 1 calc R . . C22 C 0.3196(4) 0.63872(14) 0.2832(4) 0.0223(8) Uani 1 1 d . . . H22 H 0.2171 0.6228 0.2314 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0241(2) 0.01404(19) 0.02355(19) -0.00069(13) 0.00982(15) 0.00161(14) Br2 0.0263(2) 0.0220(2) 0.0360(2) 0.00237(16) 0.00692(17) -0.00521(15) O4 0.0156(12) 0.0102(12) 0.0265(13) -0.0001(10) 0.0030(10) 0.0005(9) C2 0.0207(18) 0.0180(18) 0.0225(18) -0.0035(14) 0.0119(15) -0.0051(15) O1 0.0399(16) 0.0187(14) 0.0206(13) 0.0005(11) 0.0083(12) -0.0099(12) O2 0.0260(16) 0.0135(14) 0.072(2) -0.0166(15) 0.0050(16) -0.0047(12) C19 0.0173(17) 0.0108(16) 0.0144(15) -0.0015(13) 0.0024(13) 0.0005(13) C18 0.0225(18) 0.0146(17) 0.0172(16) -0.0001(14) 0.0087(14) -0.0040(14) C8 0.0216(19) 0.0193(19) 0.0241(18) -0.0019(14) 0.0124(16) 0.0011(15) C1 0.0182(18) 0.0218(19) 0.0204(17) -0.0017(14) 0.0083(15) -0.0017(14) C15 0.0180(17) 0.0179(18) 0.0171(16) -0.0008(14) 0.0034(14) 0.0012(14) C3 0.0179(18) 0.0224(19) 0.0217(18) -0.0045(15) 0.0076(15) -0.0043(15) O3 0.0288(16) 0.0347(17) 0.0404(17) -0.0110(14) 0.0134(13) -0.0040(13) C13 0.0169(17) 0.0191(18) 0.0173(17) -0.0007(14) 0.0004(14) 0.0008(14) C7 0.0219(18) 0.0187(19) 0.0273(19) -0.0004(15) 0.0126(16) -0.0044(15) C11 0.0166(17) 0.0140(17) 0.0196(17) -0.0016(13) 0.0079(14) 0.0004(14) C10 0.0262(19) 0.0193(19) 0.0202(18) 0.0027(14) 0.0108(16) 0.0029(15) C16 0.0160(16) 0.0115(16) 0.0155(16) -0.0031(13) 0.0010(13) 0.0007(13) C20 0.0182(17) 0.0196(18) 0.0175(16) -0.0018(14) 0.0083(14) -0.0019(14) C12 0.0218(18) 0.0169(18) 0.0164(17) 0.0023(14) 0.0023(14) 0.0018(15) C14 0.0238(18) 0.0145(18) 0.0168(16) 0.0036(14) 0.0075(15) 0.0023(14) C5 0.0280(19) 0.0184(19) 0.0179(17) -0.0052(14) 0.0130(15) -0.0048(15) C6 0.0219(18) 0.0155(18) 0.0221(18) -0.0009(14) 0.0059(15) -0.0020(14) C9 0.0131(16) 0.0121(17) 0.0285(18) -0.0038(14) 0.0066(14) 0.0017(13) C17 0.0197(17) 0.0183(18) 0.0204(17) -0.0019(14) 0.0099(14) -0.0003(14) C4 0.0212(18) 0.0212(19) 0.0184(17) -0.0008(14) 0.0060(15) -0.0009(15) N2 0.0153(14) 0.0378(19) 0.0095(13) -0.0006(13) 0.0073(12) 0.0131(13) O5 0.0392(17) 0.0206(14) 0.0363(16) 0.0044(13) 0.0180(14) -0.0027(13) O6 0.0302(15) 0.0246(15) 0.0308(15) -0.0033(12) 0.0096(13) -0.0077(12) C24 0.0210(17) 0.0124(16) 0.0202(16) -0.0019(14) 0.0132(14) -0.0005(14) C23 0.0199(18) 0.0144(17) 0.0178(16) 0.0015(13) 0.0064(14) -0.0037(14) C21 0.0218(18) 0.0180(18) 0.0278(19) 0.0042(15) 0.0120(16) 0.0014(15) C22 0.0192(18) 0.027(2) 0.0197(18) -0.0059(15) 0.0078(15) -0.0086(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C19 1.903(3) . ? Br2 C2 1.909(4) . ? O4 C11 1.383(4) . ? O4 C16 1.397(4) . ? C2 C1 1.383(5) . ? C2 C3 1.384(5) . ? O1 C5 1.379(4) . ? O1 C6 1.382(4) . ? O2 N1 1.087(4) . ? C19 C20 1.377(5) . ? C19 C18 1.384(5) . ? C18 C17 1.387(5) . ? C18 H18 0.9500 . ? C8 C7 1.381(5) . ? C8 C9 1.385(5) . ? C8 H8 0.9500 . ? C1 C22 1.395(5) . ? C1 H1 0.9500 . ? C15 C11 1.374(5) . ? C15 C14 1.387(5) . ? C15 H15 0.9500 . ? C3 C4 1.384(5) . ? C3 H3 0.9500 . ? O3 N1 1.223(4) . ? C13 C24 1.377(5) . ? C13 C12 1.381(5) . ? C13 H13 0.9500 . ? C7 C6 1.388(5) . ? C7 H7 0.9500 . ? C11 C12 1.391(5) . ? C10 C21 1.374(5) . ? C10 C6 1.389(5) . ? C10 H10 0.9500 . ? C16 C23 1.376(5) . ? C16 C17 1.385(5) . ? C20 C23 1.398(5) . ? C20 H20 0.9500 . ? C12 H12 0.9500 . ? C14 C24 1.388(5) . ? C14 H14 0.9500 . ? C5 C22 1.380(5) . ? C5 C4 1.386(5) . ? C9 C21 1.389(5) . ? C9 N1 1.532(5) . ? C17 H17 0.9500 . ? C4 H4 0.9500 . ? N2 O5 1.183(4) . ? N2 O6 1.203(4) . ? N2 C24 1.529(5) . ? C23 H23 0.9500 . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O4 C16 118.9(3) . . ? C1 C2 C3 121.9(3) . . ? C1 C2 Br2 119.6(3) . . ? C3 C2 Br2 118.5(3) . . ? C5 O1 C6 119.4(3) . . ? C20 C19 C18 121.4(3) . . ? C20 C19 Br1 120.0(3) . . ? C18 C19 Br1 118.7(3) . . ? C19 C18 C17 119.7(3) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C7 C8 C9 118.9(3) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C2 C1 C22 118.7(3) . . ? C2 C1 H1 120.7 . . ? C22 C1 H1 120.7 . . ? C11 C15 C14 119.8(3) . . ? C11 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C24 C13 C12 119.6(3) . . ? C24 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C8 C7 C6 119.0(3) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C15 C11 O4 116.3(3) . . ? C15 C11 C12 121.6(3) . . ? O4 C11 C12 121.9(3) . . ? C21 C10 C6 119.4(3) . . ? C21 C10 H10 120.3 . . ? C6 C10 H10 120.3 . . ? C23 C16 C17 121.8(3) . . ? C23 C16 O4 121.0(3) . . ? C17 C16 O4 116.9(3) . . ? C19 C20 C23 119.2(3) . . ? C19 C20 H20 120.4 . . ? C23 C20 H20 120.4 . . ? C13 C12 C11 118.7(3) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C15 C14 C24 118.5(3) . . ? C15 C14 H14 120.8 . . ? C24 C14 H14 120.8 . . ? O1 C5 C22 122.6(3) . . ? O1 C5 C4 116.1(3) . . ? C22 C5 C4 121.1(3) . . ? O1 C6 C7 121.4(3) . . ? O1 C6 C10 116.8(3) . . ? C7 C6 C10 121.7(3) . . ? C8 C9 C21 122.1(3) . . ? C8 C9 N1 119.7(3) . . ? C21 C9 N1 118.1(3) . . ? C16 C17 C18 118.8(3) . . ? C16 C17 H17 120.6 . . ? C18 C17 H17 120.6 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? O5 N2 O6 129.6(4) . . ? O5 N2 C24 115.5(3) . . ? O6 N2 C24 114.9(3) . . ? O2 N1 O3 128.2(4) . . ? O2 N1 C9 118.6(3) . . ? O3 N1 C9 113.2(3) . . ? C13 C24 C14 121.8(3) . . ? C13 C24 N2 119.2(3) . . ? C14 C24 N2 119.0(3) . . ? C16 C23 C20 119.1(3) . . ? C16 C23 H23 120.5 . . ? C20 C23 H23 120.5 . . ? C10 C21 C9 118.8(3) . . ? C10 C21 H21 120.6 . . ? C9 C21 H21 120.6 . . ? C5 C22 C1 119.6(3) . . ? C5 C22 H22 120.2 . . ? C1 C22 H22 120.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.858 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.106 # END# data_7 _database_code_depnum_ccdc_archive 'CCDC 265002' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Ethynyl-4'-nitrodiphenyl ether ; _chemical_name_common "4-Ethynyl-4'-nitrodiphenyl ether" _chemical_melting_point 357 _chemical_formula_moiety 'C14 H9 N O3' _chemical_formula_sum 'C14 H9 N O3' _chemical_formula_weight 239.22 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.866(2) _cell_length_b 8.8944(14) _cell_length_c 19.496(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.771(2) _cell_angle_gamma 90.00 _cell_volume 2393.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2926 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 19.60 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23601 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.38 _reflns_number_total 5748 _reflns_number_gt 2617 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1391P)^2^+0.0772P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5748 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1513 _refine_ls_R_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.2660 _refine_ls_wR_factor_gt 0.2134 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.31728(15) 0.1044(3) 1.00791(13) 0.0890(7) Uani 1 1 d . . . C1 C 0.4962(2) 0.3479(4) 0.93371(18) 0.0708(8) Uani 1 1 d . . . C10 C 0.0305(2) 0.2184(4) 0.96340(17) 0.0707(8) Uani 1 1 d . . . C7 C 0.2214(2) 0.1469(4) 0.99158(17) 0.0691(8) Uani 1 1 d . . . C4 C 0.3739(2) 0.1925(4) 0.98195(17) 0.0686(8) Uani 1 1 d . . . C3 C 0.3369(2) 0.2862(4) 0.92217(18) 0.0835(10) Uani 1 1 d . . . H3 H 0.2703 0.2964 0.8981 0.100 Uiso 1 1 calc R . . O2 O 0.6490(2) 0.4211(4) 0.94302(18) 0.1222(11) Uani 1 1 d . . . N1 N 0.5620(2) 0.4332(4) 0.9090(2) 0.0930(10) Uani 1 1 d . . . C2 C 0.3992(2) 0.3652(4) 0.89800(18) 0.0825(10) Uani 1 1 d . . . H2 H 0.3751 0.4296 0.8577 0.099 Uiso 1 1 calc R . . C8 C 0.1997(2) 0.2811(4) 1.01361(18) 0.0767(9) Uani 1 1 d . . . H8 H 0.2489 0.3488 1.0380 0.092 Uiso 1 1 calc R . . C9 C 0.1042(2) 0.3177(4) 0.99975(18) 0.0754(9) Uani 1 1 d . . . H9 H 0.0894 0.4103 1.0151 0.091 Uiso 1 1 calc R . . C5 C 0.4710(2) 0.1757(4) 1.01759(19) 0.0827(10) Uani 1 1 d . . . H5 H 0.4950 0.1115 1.0580 0.099 Uiso 1 1 calc R . . C6 C 0.5340(2) 0.2543(4) 0.9936(2) 0.0872(10) Uani 1 1 d . . . H6 H 0.6007 0.2441 1.0175 0.105 Uiso 1 1 calc R . . C12 C 0.1509(2) 0.0443(4) 0.9574(2) 0.0858(10) Uani 1 1 d . . . H12 H 0.1669 -0.0488 0.9434 0.103 Uiso 1 1 calc R . . C11 C 0.0555(2) 0.0803(4) 0.9439(2) 0.0877(10) Uani 1 1 d . . . H11 H 0.0073 0.0100 0.9212 0.105 Uiso 1 1 calc R . . C13 C -0.0679(3) 0.2575(4) 0.94709(19) 0.0841(10) Uani 1 1 d . . . C14 C -0.1468(3) 0.2924(4) 0.9321(2) 0.0929(11) Uani 1 1 d . . . H14 H -0.2111 0.3207 0.9199 0.111 Uiso 1 1 calc R . . O3 O 0.5285(3) 0.5149(4) 0.8564(2) 0.1434(13) Uani 1 1 d . . . O4 O 0.14049(17) 0.3829(3) 0.22012(16) 0.1008(8) Uani 1 1 d . . . C15 C 0.3374(2) 0.0923(4) 0.19146(16) 0.0702(8) Uani 1 1 d . . . C18 C 0.2032(2) 0.2787(4) 0.21019(18) 0.0732(8) Uani 1 1 d . . . C19 C 0.1808(2) 0.1303(4) 0.19430(17) 0.0730(8) Uani 1 1 d . . . H19 H 0.1202 0.0937 0.1898 0.088 Uiso 1 1 calc R . . N2 N 0.4082(2) -0.0094(4) 0.18077(16) 0.0889(8) Uani 1 1 d . . . C24 C -0.1416(2) 0.2802(3) 0.19438(17) 0.0704(8) Uani 1 1 d . . . O6 O 0.48595(18) 0.0426(3) 0.18496(16) 0.1113(9) Uani 1 1 d . . . C20 C 0.2488(2) 0.0355(4) 0.18498(18) 0.0734(8) Uani 1 1 d . . . H20 H 0.2348 -0.0658 0.1744 0.088 Uiso 1 1 calc R . . C21 C 0.0460(2) 0.3392(4) 0.2101(2) 0.0752(9) Uani 1 1 d . . . C26 C 0.0274(2) 0.2718(5) 0.2654(2) 0.0924(11) Uani 1 1 d . . . H26 H 0.0780 0.2462 0.3089 0.111 Uiso 1 1 calc R . . C17 C 0.2935(2) 0.3350(4) 0.2187(2) 0.0871(10) Uani 1 1 d . . . H17 H 0.3087 0.4352 0.2313 0.105 Uiso 1 1 calc R . . C25 C -0.0668(2) 0.2410(4) 0.25725(19) 0.0860(10) Uani 1 1 d . . . H25 H -0.0794 0.1929 0.2951 0.103 Uiso 1 1 calc R . . C16 C 0.3614(2) 0.2393(4) 0.2079(2) 0.0833(10) Uani 1 1 d . . . H16 H 0.4219 0.2751 0.2120 0.100 Uiso 1 1 calc R . . O5 O 0.3873(2) -0.1400(4) 0.16818(19) 0.1222(11) Uani 1 1 d . . . C23 C -0.1217(3) 0.3479(4) 0.13820(19) 0.0890(10) Uani 1 1 d . . . H23 H -0.1721 0.3735 0.0945 0.107 Uiso 1 1 calc R . . C22 C -0.0273(3) 0.3781(5) 0.1463(2) 0.0921(11) Uani 1 1 d . . . H22 H -0.0139 0.4247 0.1084 0.110 Uiso 1 1 calc R . . C29 C -0.3042(3) 0.2199(5) 0.1833(2) 0.0771(13) Uani 1 1 d . . . H29 H -0.3656 0.1919 0.1808 0.092 Uiso 1 1 calc R . . C28 C -0.2525(3) 0.2435(5) 0.1854(2) 0.0802(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0635(13) 0.0973(17) 0.1114(18) 0.0284(13) 0.0384(13) 0.0031(12) C1 0.069(2) 0.074(2) 0.083(2) -0.0188(17) 0.0444(17) -0.0179(16) C10 0.0576(17) 0.082(2) 0.0757(19) -0.0066(16) 0.0283(15) -0.0121(15) C7 0.0580(18) 0.077(2) 0.0755(19) 0.0117(16) 0.0280(15) -0.0059(15) C4 0.0580(17) 0.075(2) 0.0759(19) 0.0043(16) 0.0287(15) -0.0037(14) C3 0.0528(17) 0.117(3) 0.081(2) 0.017(2) 0.0248(16) -0.0057(17) O2 0.0815(19) 0.140(3) 0.165(3) -0.038(2) 0.0682(19) -0.0428(17) N1 0.091(2) 0.091(2) 0.120(3) -0.0230(19) 0.065(2) -0.0274(18) C2 0.071(2) 0.103(3) 0.079(2) 0.0147(18) 0.0330(17) -0.0042(18) C8 0.0646(19) 0.077(2) 0.086(2) -0.0001(17) 0.0247(16) -0.0213(16) C9 0.071(2) 0.074(2) 0.084(2) -0.0021(16) 0.0313(16) -0.0133(16) C5 0.0598(19) 0.098(3) 0.088(2) 0.0171(19) 0.0243(17) 0.0022(17) C6 0.0577(18) 0.103(3) 0.099(3) -0.005(2) 0.0263(18) -0.0070(18) C12 0.075(2) 0.082(2) 0.106(3) -0.0107(19) 0.040(2) -0.0097(18) C11 0.071(2) 0.091(3) 0.100(3) -0.020(2) 0.0296(19) -0.0252(18) C13 0.070(2) 0.096(3) 0.089(2) -0.0111(19) 0.0322(19) -0.0149(19) C14 0.070(2) 0.100(3) 0.111(3) -0.021(2) 0.036(2) -0.0093(19) O3 0.143(3) 0.153(3) 0.166(3) 0.037(3) 0.095(3) -0.031(2) O4 0.0753(16) 0.0727(15) 0.166(3) -0.0189(15) 0.0575(16) -0.0117(12) C15 0.0565(17) 0.086(2) 0.0701(19) 0.0076(16) 0.0261(14) 0.0026(15) C18 0.0626(18) 0.068(2) 0.091(2) 0.0014(16) 0.0311(16) -0.0060(15) C19 0.0547(17) 0.075(2) 0.088(2) -0.0092(17) 0.0244(15) -0.0138(15) N2 0.0699(19) 0.110(3) 0.091(2) 0.0104(19) 0.0356(15) 0.0058(18) C24 0.0651(18) 0.0703(19) 0.076(2) -0.0068(16) 0.0264(16) 0.0019(15) O6 0.0657(15) 0.145(3) 0.136(2) 0.0241(18) 0.0512(15) 0.0108(15) C20 0.0600(18) 0.0718(19) 0.089(2) -0.0078(16) 0.0280(16) -0.0076(15) C21 0.0622(19) 0.0653(19) 0.102(3) -0.0068(18) 0.0349(18) -0.0015(15) C26 0.064(2) 0.116(3) 0.090(2) 0.013(2) 0.0198(18) 0.0042(19) C17 0.066(2) 0.074(2) 0.120(3) 0.0010(19) 0.0342(19) -0.0188(17) C25 0.068(2) 0.111(3) 0.077(2) 0.0150(19) 0.0253(17) 0.0061(18) C16 0.0576(18) 0.089(3) 0.106(3) 0.010(2) 0.0340(17) -0.0130(17) O5 0.107(2) 0.101(2) 0.179(3) -0.017(2) 0.075(2) 0.0070(18) C23 0.079(2) 0.110(3) 0.071(2) 0.0127(19) 0.0203(17) 0.003(2) C22 0.089(3) 0.103(3) 0.094(3) 0.006(2) 0.045(2) -0.009(2) C29 0.054(2) 0.087(3) 0.073(2) 0.0082(17) 0.0035(19) -0.026(2) C28 0.108(3) 0.072(3) 0.062(2) 0.0046(18) 0.033(3) 0.028(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.377(3) . ? O1 C7 1.393(3) . ? C1 C2 1.358(4) . ? C1 C6 1.373(5) . ? C1 N1 1.454(4) . ? C10 C11 1.377(5) . ? C10 C9 1.381(4) . ? C10 C13 1.420(5) . ? C7 C8 1.347(5) . ? C7 C12 1.362(4) . ? C4 C5 1.358(4) . ? C4 C3 1.371(4) . ? C3 C2 1.377(4) . ? C3 H3 0.9300 . ? O2 N1 1.220(4) . ? N1 O3 1.203(4) . ? C2 H2 0.9300 . ? C8 C9 1.382(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C5 C6 1.382(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C12 C11 1.380(4) . ? C12 H12 0.9300 . ? C11 H11 0.9300 . ? C13 C14 1.142(5) . ? C14 H14 0.9300 . ? O4 C18 1.378(4) . ? O4 C21 1.400(4) . ? C15 C16 1.362(5) . ? C15 C20 1.372(4) . ? C15 N2 1.461(4) . ? C18 C19 1.368(4) . ? C18 C17 1.384(4) . ? C19 C20 1.379(4) . ? C19 H19 0.9300 . ? N2 O5 1.205(4) . ? N2 O6 1.219(4) . ? C24 C25 1.360(4) . ? C24 C23 1.375(5) . ? C24 C28 1.625(5) . ? C20 H20 0.9300 . ? C21 C26 1.349(5) . ? C21 C22 1.360(5) . ? C26 C25 1.377(4) . ? C26 H26 0.9300 . ? C17 C16 1.394(5) . ? C17 H17 0.9300 . ? C25 H25 0.9300 . ? C16 H16 0.9300 . ? C23 C22 1.379(5) . ? C23 H23 0.9300 . ? C22 H22 0.9300 . ? C29 C28 0.784(4) . ? C29 H29 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C7 118.4(2) . . ? C2 C1 C6 121.8(3) . . ? C2 C1 N1 119.2(3) . . ? C6 C1 N1 119.0(3) . . ? C11 C10 C9 117.9(3) . . ? C11 C10 C13 121.2(3) . . ? C9 C10 C13 120.9(3) . . ? C8 C7 C12 121.2(3) . . ? C8 C7 O1 120.8(3) . . ? C12 C7 O1 117.8(3) . . ? C5 C4 C3 121.1(3) . . ? C5 C4 O1 115.4(3) . . ? C3 C4 O1 123.4(3) . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? O3 N1 O2 122.5(3) . . ? O3 N1 C1 118.7(4) . . ? O2 N1 C1 118.8(4) . . ? C1 C2 C3 119.2(3) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C7 C8 C9 119.7(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C10 C9 C8 120.8(3) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 118.7(3) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C7 C12 C11 119.2(3) . . ? C7 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C10 C11 C12 121.2(3) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C14 C13 C10 177.6(4) . . ? C13 C14 H14 180.0 . . ? C18 O4 C21 119.3(2) . . ? C16 C15 C20 122.3(3) . . ? C16 C15 N2 119.2(3) . . ? C20 C15 N2 118.5(3) . . ? C19 C18 O4 124.1(3) . . ? C19 C18 C17 121.4(3) . . ? O4 C18 C17 114.6(3) . . ? C18 C19 C20 119.4(3) . . ? C18 C19 H19 120.3 . . ? C20 C19 H19 120.3 . . ? O5 N2 O6 123.2(3) . . ? O5 N2 C15 118.7(3) . . ? O6 N2 C15 118.1(3) . . ? C25 C24 C23 119.0(3) . . ? C25 C24 C28 120.2(3) . . ? C23 C24 C28 120.7(3) . . ? C15 C20 C19 119.2(3) . . ? C15 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C26 C21 C22 120.8(3) . . ? C26 C21 O4 120.3(3) . . ? C22 C21 O4 118.6(3) . . ? C21 C26 C25 119.8(3) . . ? C21 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C18 C17 C16 119.0(3) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C24 C25 C26 120.6(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C15 C16 C17 118.7(3) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C21 C22 C23 119.4(3) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C28 C29 H29 180.0 . . ? C29 C28 C24 175.1(7) . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.542 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.049 # END# data_8 _database_code_depnum_ccdc_archive 'CCDC 265003' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-Iodophenoxy)benzonitrile ; _chemical_name_common 4-(4-Iodophenoxy)benzonitrile _chemical_melting_point 354 _chemical_formula_moiety 'C13 H8 I N O' _chemical_formula_sum 'C13 H8 I N O' _chemical_formula_weight 321.10 _chemical_absolute_configuration ' unk' 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.325(4) _cell_length_b 7.960(5) _cell_length_c 28.285(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1198.8(14) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2074 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 25.07 _exptl_crystal_description Pellet _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.779 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 2.648 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6195 _exptl_absorpt_correction_T_max 0.8363 _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6353 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2100 _reflns_number_gt 1815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(6) _refine_ls_number_reflns 2100 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1102 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.14590(10) 1.01198(6) -0.103482(16) 0.0658(2) Uani 1 1 d . . . C1 C 0.2199(11) 1.0071(8) -0.0304(2) 0.0435(14) Uani 1 1 d . . . C6 C 0.3114(11) 1.0071(9) 0.0651(2) 0.0471(15) Uani 1 1 d . . . C5 C 0.1051(12) 1.0841(9) 0.0477(3) 0.0488(17) Uani 1 1 d . . . H5 H -0.0067 1.1367 0.0682 0.059 Uiso 1 1 calc R . . C2 C 0.4288(14) 0.9308(8) -0.0137(3) 0.0520(18) Uani 1 1 d . . . H2 H 0.5398 0.8792 -0.0346 0.062 Uiso 1 1 calc R . . C3 C 0.0594(14) 1.0851(8) -0.0006(3) 0.0484(17) Uani 1 1 d . . . H3 H -0.0817 1.1395 -0.0125 0.058 Uiso 1 1 calc R . . C4 C 0.4777(12) 0.9296(8) 0.0351(3) 0.0489(18) Uani 1 1 d . . . H4 H 0.6206 0.8771 0.0469 0.059 Uiso 1 1 calc R . . O1 O 0.3778(8) 1.0072(7) 0.11247(17) 0.0686(14) Uani 1 1 d . . . C7 C 0.1863(11) 1.0091(11) 0.1453(2) 0.0551(19) Uani 1 1 d . . . C10 C -0.1847(13) 1.0112(10) 0.2125(2) 0.0568(17) Uani 1 1 d . . . C9 C -0.128(2) 0.8666(10) 0.1885(3) 0.078(3) Uani 1 1 d . . . H9 H -0.2136 0.7677 0.1954 0.093 Uiso 1 1 calc R . . C12 C 0.133(2) 1.1564(9) 0.1689(3) 0.066(2) Uani 1 1 d . . . H12 H 0.2196 1.2548 0.1619 0.079 Uiso 1 1 calc R . . C11 C -0.051(2) 1.1544(10) 0.2028(3) 0.071(3) Uani 1 1 d . . . H11 H -0.0857 1.2522 0.2196 0.086 Uiso 1 1 calc R . . C8 C 0.0549(18) 0.8673(11) 0.1539(3) 0.070(3) Uani 1 1 d . . . H8 H 0.0876 0.7705 0.1366 0.083 Uiso 1 1 calc R . . C13 C -0.3717(17) 1.0093(10) 0.2495(3) 0.073(2) Uani 1 1 d . . . N1 N -0.5151(17) 1.0093(10) 0.2788(3) 0.094(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0806(4) 0.0683(3) 0.0486(3) -0.0004(2) -0.0042(2) 0.0050(4) C1 0.041(3) 0.044(3) 0.046(3) -0.004(3) -0.004(3) 0.001(4) C6 0.038(3) 0.051(3) 0.053(4) 0.009(4) 0.001(3) -0.001(5) C5 0.028(4) 0.055(4) 0.063(5) 0.000(3) 0.007(3) 0.005(3) C2 0.047(4) 0.057(4) 0.052(4) -0.007(3) 0.009(4) 0.002(3) C3 0.039(4) 0.052(4) 0.054(4) 0.005(3) -0.004(4) 0.008(3) C4 0.025(3) 0.057(4) 0.065(5) 0.011(3) -0.007(3) 0.003(3) O1 0.055(3) 0.101(4) 0.050(3) 0.005(3) -0.007(2) -0.002(4) C7 0.043(3) 0.073(5) 0.049(4) -0.001(4) -0.004(3) -0.007(7) C10 0.064(4) 0.070(5) 0.037(3) 0.012(4) -0.002(3) 0.006(6) C9 0.099(7) 0.066(5) 0.069(5) -0.007(4) 0.012(7) -0.024(6) C12 0.078(6) 0.057(4) 0.062(5) 0.001(4) 0.001(6) -0.009(5) C11 0.093(8) 0.060(5) 0.060(5) -0.003(4) 0.003(5) 0.001(5) C8 0.081(7) 0.073(5) 0.055(5) -0.022(4) 0.012(5) -0.010(5) C13 0.088(5) 0.074(5) 0.057(5) 0.000(5) 0.010(5) 0.000(8) N1 0.117(6) 0.094(5) 0.071(5) 0.001(5) 0.039(5) 0.012(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.106(6) . ? C1 C3 1.351(9) . ? C1 C2 1.352(10) . ? C6 C5 1.350(9) . ? C6 C4 1.373(10) . ? C6 O1 1.386(8) . ? C5 C3 1.388(10) . ? C5 H5 0.9300 . ? C2 C4 1.405(9) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? O1 C7 1.380(8) . ? C7 C8 1.350(11) . ? C7 C12 1.378(11) . ? C10 C9 1.371(11) . ? C10 C11 1.372(11) . ? C10 C13 1.444(11) . ? C9 C8 1.381(12) . ? C9 H9 0.9300 . ? C12 C11 1.371(12) . ? C12 H12 0.9300 . ? C11 H11 0.9300 . ? C8 H8 0.9300 . ? C13 N1 1.125(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 C2 120.7(6) . . ? C3 C1 I1 119.0(5) . . ? C2 C1 I1 120.3(5) . . ? C5 C6 C4 120.2(7) . . ? C5 C6 O1 124.0(6) . . ? C4 C6 O1 115.7(6) . . ? C6 C5 C3 120.2(7) . . ? C6 C5 H5 119.9 . . ? C3 C5 H5 119.9 . . ? C1 C2 C4 119.8(6) . . ? C1 C2 H2 120.1 . . ? C4 C2 H2 120.1 . . ? C1 C3 C5 120.0(6) . . ? C1 C3 H3 120.0 . . ? C5 C3 H3 120.0 . . ? C6 C4 C2 119.0(6) . . ? C6 C4 H4 120.5 . . ? C2 C4 H4 120.5 . . ? C7 O1 C6 117.6(5) . . ? C8 C7 C12 121.2(7) . . ? C8 C7 O1 119.6(7) . . ? C12 C7 O1 119.2(8) . . ? C9 C10 C11 119.0(7) . . ? C9 C10 C13 120.2(8) . . ? C11 C10 C13 120.8(8) . . ? C10 C9 C8 120.2(8) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C12 C7 118.4(8) . . ? C11 C12 H12 120.8 . . ? C7 C12 H12 120.8 . . ? C12 C11 C10 121.4(7) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C7 C8 C9 119.8(7) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? N1 C13 C10 179.0(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.028 _refine_diff_density_min -0.612 _refine_diff_density_rms 0.113 # END# data_9 _database_code_depnum_ccdc_archive 'CCDC 265004' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-Iodophenoxy)benzonitrile ; _chemical_name_common 4-(4-Iodophenoxy)benzonitrile _chemical_melting_point 356 _chemical_formula_moiety 'C13 H8 Cl N O' _chemical_formula_sum 'C13 H8 Cl N O' _chemical_formula_weight 229.65 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3125(17) _cell_length_b 7.3792(10) _cell_length_c 11.8045(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.385(2) _cell_angle_gamma 90.00 _cell_volume 1061.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3118 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.28 _exptl_crystal_description Block _exptl_crystal_colour Block _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.333 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8563 _exptl_absorpt_correction_T_max 0.9272 _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6929 _diffrn_reflns_av_R_equivalents 0.0649 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2529 _reflns_number_gt 2145 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.1846P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2529 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C9 C 0.07072(11) 0.1235(2) 0.85350(14) 0.0331(4) Uani 1 1 d . . . H9 H 0.0169 0.1897 0.8828 0.040 Uiso 1 1 calc R . . C1 C 0.24087(12) 0.0333(2) 1.23083(14) 0.0326(3) Uani 1 1 d . . . H1 H 0.1775 -0.0213 1.2488 0.039 Uiso 1 1 calc R . . O1 O 0.15136(8) 0.06367(17) 1.04293(10) 0.0425(3) Uani 1 1 d . . . C6 C 0.24621(12) 0.0867(2) 1.11959(14) 0.0336(4) Uani 1 1 d . A . C12 C 0.15550(12) 0.0455(2) 0.92688(14) 0.0351(4) Uani 1 1 d . B . C11 C 0.14763(12) 0.0037(2) 0.69440(14) 0.0324(3) Uani 1 1 d . . . C4 C 0.42876(12) 0.1980(2) 1.17589(15) 0.0361(4) Uani 1 1 d . A . H4 H 0.4920 0.2531 1.1579 0.043 Uiso 1 1 calc R . . C2 C 0.32918(13) 0.0607(2) 1.31520(14) 0.0336(4) Uani 1 1 d . A . H2 H 0.3259 0.0239 1.3900 0.040 Uiso 1 1 calc R . . C3 C 0.42341(12) 0.1441(2) 1.28747(14) 0.0313(3) Uani 1 1 d . . . C10 C 0.06599(11) 0.1030(2) 0.73678(15) 0.0350(4) Uani 1 1 d . B . H10 H 0.0090 0.1547 0.6869 0.042 Uiso 1 1 calc R . . C8 C 0.23238(13) -0.0735(2) 0.76830(16) 0.0404(4) Uani 1 1 d . B . H8 H 0.2868 -0.1385 0.7391 0.048 Uiso 1 1 calc R . . C18 C 0.23659(13) -0.0548(2) 0.88520(16) 0.0425(4) Uani 1 1 d . . . H18 H 0.2928 -0.1084 0.9352 0.051 Uiso 1 1 calc R B . C20 C 0.34028(12) 0.1700(2) 1.09162(15) 0.0379(4) Uani 1 1 d . . . H20 H 0.3434 0.2064 1.0167 0.046 Uiso 1 1 calc R A . C26 C 0.5071(4) 0.1759(10) 1.3689(6) 0.0312(13) Uani 0.50 1 d P A 1 N2 N 0.5697(5) 0.2012(11) 1.4327(6) 0.0393(15) Uani 0.50 1 d P A 1 C25 C 0.1488(4) -0.0247(7) 0.5890(4) 0.0356(11) Uani 0.50 1 d P B 1 N1 N 0.1480(4) -0.0536(6) 0.4802(4) 0.0490(12) Uani 0.50 1 d P B 1 Cl1 Cl 0.14181(10) -0.02214(19) 0.53199(15) 0.0448(3) Uani 0.50 1 d P B 2 Cl2 Cl 0.54207(11) 0.1831(2) 1.40077(13) 0.0273(4) Uani 0.50 1 d P A 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C9 0.0190(6) 0.0335(8) 0.0478(10) -0.0002(7) 0.0088(6) 0.0001(5) C1 0.0338(7) 0.0280(7) 0.0411(9) 0.0035(6) 0.0218(6) 0.0022(6) O1 0.0264(5) 0.0619(8) 0.0420(7) 0.0202(6) 0.0140(5) 0.0075(5) C6 0.0284(7) 0.0314(8) 0.0440(9) 0.0117(6) 0.0156(6) 0.0096(6) C12 0.0261(7) 0.0347(8) 0.0470(10) 0.0132(7) 0.0139(6) 0.0000(6) C11 0.0277(7) 0.0283(7) 0.0433(9) -0.0013(6) 0.0124(6) -0.0072(5) C4 0.0314(7) 0.0319(8) 0.0492(10) 0.0118(7) 0.0204(7) 0.0047(6) C2 0.0420(8) 0.0273(7) 0.0362(8) 0.0003(6) 0.0218(7) 0.0008(6) C3 0.0324(7) 0.0248(7) 0.0402(9) -0.0010(6) 0.0170(7) 0.0030(6) C10 0.0219(6) 0.0337(8) 0.0488(10) -0.0033(7) 0.0036(6) -0.0013(6) C8 0.0324(8) 0.0308(8) 0.0625(12) 0.0101(7) 0.0219(7) 0.0069(6) C18 0.0336(8) 0.0424(9) 0.0547(11) 0.0214(8) 0.0169(7) 0.0132(7) C20 0.0317(7) 0.0399(9) 0.0464(9) 0.0197(7) 0.0195(7) 0.0092(6) C26 0.031(3) 0.0305(19) 0.035(4) -0.004(2) 0.016(2) -0.006(3) N2 0.031(3) 0.045(2) 0.044(4) -0.005(3) 0.011(2) -0.007(2) C25 0.0312(18) 0.039(2) 0.036(3) 0.007(2) 0.005(2) -0.0040(13) N1 0.055(2) 0.060(3) 0.037(3) -0.0153(19) 0.0205(19) -0.0026(17) Cl1 0.0339(5) 0.0482(6) 0.0527(11) -0.0028(9) 0.0080(8) -0.0073(4) Cl2 0.0178(10) 0.0405(7) 0.0225(11) -0.0084(7) -0.0005(6) -0.0064(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C9 C10 1.379(2) . ? C9 C12 1.381(2) . ? C9 H9 0.9300 . ? C1 C2 1.378(2) . ? C1 C6 1.382(2) . ? C1 H1 0.9300 . ? O1 C6 1.380(2) . ? O1 C12 1.385(2) . ? C6 C20 1.393(2) . ? C12 C18 1.389(2) . ? C11 C25 1.263(5) . ? C11 C8 1.382(2) . ? C11 C10 1.394(2) . ? C11 Cl1 1.918(2) . ? C4 C20 1.379(2) . ? C4 C3 1.387(2) . ? C4 H4 0.9300 . ? C2 C3 1.394(2) . ? C2 H2 0.9300 . ? C3 C26 1.323(6) . ? C3 Cl2 1.854(2) . ? C10 H10 0.9300 . ? C8 C18 1.380(3) . ? C8 H8 0.9300 . ? C18 H18 0.9300 . ? C20 H20 0.9300 . ? C26 N2 1.013(7) . ? C25 N1 1.301(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C9 C12 119.93(14) . . ? C10 C9 H9 120.0 . . ? C12 C9 H9 120.0 . . ? C2 C1 C6 120.20(14) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C6 O1 C12 120.73(11) . . ? O1 C6 C1 115.80(13) . . ? O1 C6 C20 123.54(14) . . ? C1 C6 C20 120.50(15) . . ? C9 C12 O1 116.52(13) . . ? C9 C12 C18 121.08(16) . . ? O1 C12 C18 122.29(14) . . ? C25 C11 C8 115.9(3) . . ? C25 C11 C10 123.5(3) . . ? C8 C11 C10 120.52(15) . . ? C25 C11 Cl1 4.7(3) . . ? C8 C11 Cl1 120.32(12) . . ? C10 C11 Cl1 119.16(13) . . ? C20 C4 C3 120.00(14) . . ? C20 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C1 C2 C3 119.43(14) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C26 C3 C4 120.0(3) . . ? C26 C3 C2 119.6(3) . . ? C4 C3 C2 120.40(15) . . ? C26 C3 Cl2 1.4(3) . . ? C4 C3 Cl2 119.95(12) . . ? C2 C3 Cl2 119.64(13) . . ? C9 C10 C11 119.24(14) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C18 C8 C11 120.30(14) . . ? C18 C8 H8 119.8 . . ? C11 C8 H8 119.8 . . ? C8 C18 C12 118.91(15) . . ? C8 C18 H18 120.5 . . ? C12 C18 H18 120.5 . . ? C4 C20 C6 119.46(15) . . ? C4 C20 H20 120.3 . . ? C6 C20 H20 120.3 . . ? N2 C26 C3 178.5(11) . . ? C11 C25 N1 179.0(5) . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.211 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.048 # END# data_10 _database_code_depnum_ccdc_archive 'CCDC 265005' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-Ethynylphenoxy)benzonitrile ; _chemical_name_common 4-(4-Ethynylphenoxy)benzonitrile _chemical_melting_point 349 _chemical_formula_moiety 'C15 H9 N O' _chemical_formula_sum 'C15 H9 N O' _chemical_formula_weight 219.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 15.5731(11) _cell_length_b 21.7581(16) _cell_length_c 18.1368(13) _cell_angle_alpha 90.00 _cell_angle_beta 111.5700(10) _cell_angle_gamma 90.00 _cell_volume 5715.1(7) _cell_formula_units_Z 20 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9913 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 26.97 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2280 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37459 _diffrn_reflns_av_R_equivalents 0.0712 _diffrn_reflns_av_sigmaI/netI 0.0826 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 10072 _reflns_number_gt 6469 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10072 _refine_ls_number_parameters 766 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0882 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.01952(9) 0.66330(7) 0.57564(8) 0.0278(4) Uani 1 1 d . . . O5 O 0.65052(9) 0.59002(8) 0.49828(8) 0.0371(4) Uani 1 1 d . . . C1 C -0.15964(14) 0.63033(9) 0.69132(11) 0.0210(5) Uani 1 1 d . . . C2 C -0.17560(14) 0.67740(10) 0.63573(12) 0.0246(5) Uani 1 1 d . . . H2 H -0.2300 0.7017 0.6221 0.030 Uiso 1 1 calc R . . C3 C 0.55631(14) 0.58109(11) 0.46167(12) 0.0273(6) Uani 1 1 d . . . C4 C 0.17434(14) 0.66787(10) 0.67470(12) 0.0265(5) Uani 1 1 d . . . H4 H 0.1532 0.6896 0.7102 0.032 Uiso 1 1 calc R . . C5 C 0.11240(13) 0.64671(10) 0.60338(12) 0.0213(5) Uani 1 1 d . . . C6 C -0.22852(15) 0.61692(10) 0.72452(12) 0.0249(5) Uani 1 1 d . . . C7 C -0.11270(14) 0.68869(10) 0.60062(12) 0.0247(5) Uani 1 1 d . . . H7 H -0.1234 0.7208 0.5628 0.030 Uiso 1 1 calc R . . C8 C 0.91330(16) 0.54803(10) 0.36099(13) 0.0308(6) Uani 1 1 d . . . C9 C 0.79577(14) 0.55525(10) 0.50622(12) 0.0272(6) Uani 1 1 d . . . H9 H 0.8097 0.5476 0.5610 0.033 Uiso 1 1 calc R . . C10 C 0.84195(14) 0.55668(10) 0.39308(12) 0.0244(5) Uani 1 1 d . . . N2 N -0.28553(12) 0.60694(9) 0.74893(10) 0.0334(5) Uani 1 1 d . . . C11 C 0.26765(14) 0.65718(10) 0.69411(12) 0.0261(5) Uani 1 1 d . . . H11 H 0.3106 0.6721 0.7430 0.031 Uiso 1 1 calc R . . C12 C 0.23526(14) 0.60218(10) 0.57263(12) 0.0264(5) Uani 1 1 d . . . H12 H 0.2557 0.5789 0.5379 0.032 Uiso 1 1 calc R . . C13 C 0.26929(16) 0.55741(11) 0.37033(12) 0.0296(6) Uani 1 1 d . . . C14 C 0.50150(15) 0.62134(10) 0.48348(12) 0.0293(6) Uani 1 1 d . . . H14 H 0.5286 0.6544 0.5185 0.035 Uiso 1 1 calc R . . C15 C 0.29950(14) 0.62487(9) 0.64284(12) 0.0219(5) Uani 1 1 d . . . C16 C -0.03365(13) 0.65315(10) 0.62035(12) 0.0216(5) Uani 1 1 d . . . C17 C 0.39724(15) 0.61668(10) 0.66267(12) 0.0250(5) Uani 1 1 d . . . C18 C 0.70958(14) 0.57578(10) 0.45886(13) 0.0259(5) Uani 1 1 d . . . C19 C -0.07890(13) 0.59595(10) 0.71242(11) 0.0232(5) Uani 1 1 d . . . H19 H -0.0671 0.5647 0.7515 0.028 Uiso 1 1 calc R . . C20 C -0.01556(14) 0.60703(9) 0.67667(11) 0.0216(5) Uani 1 1 d . . . H20 H 0.0394 0.5834 0.6906 0.026 Uiso 1 1 calc R . . C21 C 0.75381(15) 0.57681(10) 0.34649(13) 0.0302(6) Uani 1 1 d . . . H21 H 0.7390 0.5839 0.2915 0.036 Uiso 1 1 calc R . . C22 C 0.51829(14) 0.53267(10) 0.41101(12) 0.0305(6) Uani 1 1 d . . . H22 H 0.5568 0.5049 0.3969 0.037 Uiso 1 1 calc R . . C23 C 0.86199(14) 0.54590(10) 0.47337(12) 0.0276(6) Uani 1 1 d . . . H23 H 0.9218 0.5320 0.5059 0.033 Uiso 1 1 calc R . . C24 C 0.97299(17) 0.54251(10) 0.33802(14) 0.0373(6) Uani 1 1 d . . . H24 H 1.0220 0.5380 0.3191 0.045 Uiso 1 1 calc R . . N5 N 0.19010(14) 0.55123(10) 0.34397(11) 0.0447(6) Uani 1 1 d . . . C25 C 0.14158(14) 0.61315(10) 0.55254(12) 0.0243(5) Uani 1 1 d . . . H25 H 0.0981 0.5977 0.5043 0.029 Uiso 1 1 calc R . . C26 C 0.40690(15) 0.61325(10) 0.45406(12) 0.0292(6) Uani 1 1 d . . . H26 H 0.3687 0.6406 0.4691 0.035 Uiso 1 1 calc R . . C27 C 0.68762(15) 0.58658(10) 0.37907(12) 0.0304(6) Uani 1 1 d . . . H27 H 0.6277 0.6006 0.3470 0.037 Uiso 1 1 calc R . . C28 C 0.36765(14) 0.56493(10) 0.40239(12) 0.0259(5) Uani 1 1 d . . . C29 C 0.42396(14) 0.52506(10) 0.38125(12) 0.0300(6) Uani 1 1 d . . . H29 H 0.3972 0.4921 0.3459 0.036 Uiso 1 1 calc R . . C30 C 0.47790(16) 0.61117(10) 0.67972(12) 0.0326(6) Uani 1 1 d . . . H30 H 0.5426 0.6068 0.6934 0.039 Uiso 1 1 calc R . . O4 O 0.23848(9) 0.24476(7) 0.13114(8) 0.0320(4) Uani 1 1 d . . . O3 O 0.58325(9) 0.31733(7) 0.11107(8) 0.0305(4) Uani 1 1 d . . . C32 C 0.17683(14) 0.23625(10) 0.16892(12) 0.0238(5) Uani 1 1 d . . . N4 N 0.69221(13) 0.18028(10) 0.27766(11) 0.0411(6) Uani 1 1 d . . . C34 C -0.03670(15) 0.20657(10) 0.25551(12) 0.0258(5) Uani 1 1 d . . . C35 C 0.09946(14) 0.27347(10) 0.14257(12) 0.0246(5) Uani 1 1 d . . . H35 H 0.0944 0.3050 0.1049 0.030 Uiso 1 1 calc R . . C36 C 0.44422(14) 0.35523(10) 0.11374(12) 0.0241(5) Uani 1 1 d . . . H36 H 0.4786 0.3734 0.1635 0.029 Uiso 1 1 calc R . . C37 C 0.77548(14) 0.30079(10) 0.00359(12) 0.0228(5) Uani 1 1 d . . . C38 C 0.03629(14) 0.21800(10) 0.22594(12) 0.0212(5) Uani 1 1 d . . . C39 C 0.11530(14) 0.18140(10) 0.25190(12) 0.0247(5) Uani 1 1 d . . . H39 H 0.1208 0.1498 0.2895 0.030 Uiso 1 1 calc R . . C40 C 0.44098(13) 0.30018(10) -0.00283(11) 0.0240(5) Uani 1 1 d . . . H40 H 0.4729 0.2806 -0.0320 0.029 Uiso 1 1 calc R . . C41 C 0.02980(14) 0.26466(10) 0.17114(12) 0.0248(5) Uani 1 1 d . . . H41 H -0.0231 0.2905 0.1535 0.030 Uiso 1 1 calc R . . C42 C 0.84770(15) 0.29766(10) -0.02892(12) 0.0279(6) Uani 1 1 d . . . C43 C 0.51664(14) 0.20271(10) 0.22533(12) 0.0236(5) Uani 1 1 d . . . C44 C 0.46312(14) 0.18932(9) 0.14724(12) 0.0249(5) Uani 1 1 d . . . H44 H 0.4908 0.1717 0.1135 0.030 Uiso 1 1 calc R . . C45 C 0.38236(14) 0.24242(10) 0.24505(12) 0.0280(6) Uani 1 1 d . . . H45 H 0.3544 0.2608 0.2781 0.034 Uiso 1 1 calc R . . C46 C 0.64184(13) 0.31024(10) 0.06961(12) 0.0231(5) Uani 1 1 d . . . C47 C 0.33046(14) 0.22827(10) 0.16741(12) 0.0241(5) Uani 1 1 d . . . C48 C 0.61368(15) 0.19031(10) 0.25476(12) 0.0276(6) Uani 1 1 d . . . C49 C 0.34901(14) 0.35873(9) 0.08339(12) 0.0242(5) Uani 1 1 d . . . H49 H 0.3174 0.3786 0.1126 0.029 Uiso 1 1 calc R . . C50 C 0.36962(14) 0.20157(9) 0.11840(12) 0.0243(5) Uani 1 1 d . . . H50 H 0.3325 0.1917 0.0652 0.029 Uiso 1 1 calc R . . C51 C 0.29945(13) 0.33283(10) 0.00949(12) 0.0219(5) Uani 1 1 d . . . C52 C 0.47617(14) 0.22943(10) 0.27428(12) 0.0271(6) Uani 1 1 d . . . H52 H 0.5128 0.2388 0.3278 0.032 Uiso 1 1 calc R . . C53 C 0.71103(14) 0.26722(10) 0.09899(12) 0.0268(6) Uani 1 1 d . . . H53 H 0.7131 0.2413 0.1418 0.032 Uiso 1 1 calc R . . C54 C 0.18544(14) 0.19032(10) 0.22397(12) 0.0259(5) Uani 1 1 d . . . H54 H 0.2391 0.1653 0.2423 0.031 Uiso 1 1 calc R . . C55 C 0.63701(14) 0.34820(10) 0.00722(12) 0.0242(5) Uani 1 1 d . . . H55 H 0.5882 0.3771 -0.0130 0.029 Uiso 1 1 calc R . . C56 C 0.34579(13) 0.30434(9) -0.03354(12) 0.0233(5) Uani 1 1 d . . . H56 H 0.3119 0.2876 -0.0844 0.028 Uiso 1 1 calc R . . C57 C 0.20027(15) 0.33393(10) -0.02062(12) 0.0273(6) Uani 1 1 d . . . C58 C 0.48901(13) 0.32514(10) 0.07136(12) 0.0229(5) Uani 1 1 d . . . C59 C 0.70399(14) 0.34356(10) -0.02533(12) 0.0255(5) Uani 1 1 d . . . H59 H 0.7015 0.3698 -0.0679 0.031 Uiso 1 1 calc R . . C60 C 0.77741(14) 0.26221(10) 0.06536(12) 0.0265(5) Uani 1 1 d . . . H60 H 0.8247 0.2322 0.0846 0.032 Uiso 1 1 calc R . . N3 N 0.12044(13) 0.33407(9) -0.04373(11) 0.0387(5) Uani 1 1 d . . . C33 C -0.09474(15) 0.19496(10) 0.27890(12) 0.0283(6) Uani 1 1 d . . . H33 H -0.1423 0.1854 0.2981 0.034 Uiso 1 1 calc R . . C61 C 0.90630(15) 0.29676(11) -0.05363(13) 0.0335(6) Uani 1 1 d . . . H61 H 0.9545 0.2960 -0.0740 0.040 Uiso 1 1 calc R . . O1 O 0.15613(9) 0.54948(7) 0.94978(8) 0.0357(4) Uani 1 1 d . . . C63 C -0.04759(14) 0.45388(10) 0.84915(11) 0.0250(5) Uani 1 1 d . . . H63 H -0.0650 0.4167 0.8199 0.030 Uiso 1 1 calc R . . C64 C -0.08741(14) 0.54251(10) 0.90983(11) 0.0237(5) Uani 1 1 d . . . H64 H -0.1322 0.5659 0.9217 0.028 Uiso 1 1 calc R . . C65 C 0.44341(16) 0.47984(11) 0.85104(13) 0.0313(6) Uani 1 1 d . . . C66 C 0.22324(14) 0.52774(10) 0.92173(13) 0.0286(6) Uani 1 1 d . . . C67 C 0.00239(14) 0.56236(10) 0.93499(11) 0.0231(5) Uani 1 1 d . . . H67 H 0.0200 0.5995 0.9642 0.028 Uiso 1 1 calc R . . N1 N -0.28263(13) 0.45113(9) 0.82487(11) 0.0338(5) Uani 1 1 d . . . C68 C -0.20720(15) 0.46689(10) 0.84251(12) 0.0257(5) Uani 1 1 d . . . C69 C 0.04322(14) 0.47390(10) 0.87412(11) 0.0248(5) Uani 1 1 d . . . H69 H 0.0881 0.4511 0.8617 0.030 Uiso 1 1 calc R . . C70 C 0.36697(14) 0.49499(10) 0.87500(13) 0.0266(5) Uani 1 1 d . . . C71 C 0.06721(14) 0.52779(10) 0.91750(12) 0.0248(5) Uani 1 1 d . . . C72 C -0.11324(14) 0.48775(10) 0.86664(11) 0.0222(5) Uani 1 1 d . . . C73 C 0.29661(14) 0.49578(10) 0.97349(13) 0.0296(6) Uani 1 1 d . . . H73 H 0.2980 0.4850 1.0247 0.035 Uiso 1 1 calc R . . C74 C 0.36869(15) 0.47947(10) 0.94982(13) 0.0300(6) Uani 1 1 d . . . H74 H 0.4199 0.4574 0.9852 0.036 Uiso 1 1 calc R . . C75 C 0.50519(16) 0.46912(11) 0.83158(13) 0.0378(6) Uani 1 1 d . . . H75 H 0.5556 0.4604 0.8157 0.045 Uiso 1 1 calc R . . C76 C 0.21977(15) 0.54345(11) 0.84730(13) 0.0361(6) Uani 1 1 d . . . H76 H 0.1682 0.5654 0.8122 0.043 Uiso 1 1 calc R . . C77 C 0.29148(15) 0.52729(11) 0.82376(13) 0.0333(6) Uani 1 1 d . . . H77 H 0.2893 0.5382 0.7724 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0197(9) 0.0370(10) 0.0267(8) 0.0096(7) 0.0084(7) 0.0046(8) O5 0.0220(9) 0.0580(12) 0.0323(9) -0.0155(8) 0.0111(7) -0.0057(8) C1 0.0197(12) 0.0217(13) 0.0202(11) -0.0022(10) 0.0059(9) -0.0017(10) C2 0.0199(12) 0.0217(13) 0.0290(13) 0.0004(10) 0.0051(10) 0.0035(10) C3 0.0218(13) 0.0349(15) 0.0253(12) 0.0003(11) 0.0089(10) -0.0022(12) C4 0.0275(13) 0.0276(14) 0.0268(13) -0.0028(10) 0.0128(10) 0.0044(11) C5 0.0182(12) 0.0207(13) 0.0240(12) 0.0074(10) 0.0067(9) 0.0016(10) C6 0.0234(13) 0.0230(14) 0.0256(13) -0.0013(10) 0.0058(10) 0.0051(11) C7 0.0235(13) 0.0201(13) 0.0274(12) 0.0066(10) 0.0059(10) 0.0027(11) C8 0.0330(14) 0.0225(14) 0.0387(15) -0.0015(11) 0.0153(12) -0.0030(12) C9 0.0272(13) 0.0285(14) 0.0220(12) -0.0029(10) 0.0045(10) -0.0052(11) C10 0.0252(13) 0.0176(12) 0.0328(13) -0.0031(10) 0.0134(10) -0.0010(11) N2 0.0309(12) 0.0363(13) 0.0352(12) -0.0009(10) 0.0150(10) 0.0034(10) C11 0.0241(13) 0.0274(14) 0.0233(12) -0.0024(10) 0.0045(10) -0.0009(11) C12 0.0296(14) 0.0259(14) 0.0259(12) -0.0031(10) 0.0128(10) 0.0011(11) C13 0.0288(14) 0.0320(15) 0.0274(13) 0.0052(11) 0.0097(11) 0.0022(12) C14 0.0311(14) 0.0304(14) 0.0273(13) -0.0056(11) 0.0116(11) -0.0042(12) C15 0.0239(13) 0.0186(12) 0.0238(12) 0.0011(10) 0.0096(10) 0.0009(10) C16 0.0197(12) 0.0210(13) 0.0224(12) -0.0019(10) 0.0056(10) -0.0019(10) C17 0.0266(14) 0.0274(14) 0.0216(12) -0.0046(10) 0.0095(10) -0.0001(11) C18 0.0218(13) 0.0267(14) 0.0309(13) -0.0062(11) 0.0116(10) -0.0042(11) C19 0.0236(13) 0.0238(13) 0.0195(11) 0.0013(10) 0.0048(10) -0.0008(11) C20 0.0186(12) 0.0203(13) 0.0231(12) 0.0006(10) 0.0044(9) 0.0019(10) C21 0.0346(14) 0.0301(14) 0.0272(13) 0.0037(11) 0.0129(11) 0.0044(12) C22 0.0259(14) 0.0323(15) 0.0316(13) -0.0052(11) 0.0086(11) 0.0022(12) C23 0.0218(13) 0.0254(14) 0.0308(13) -0.0032(11) 0.0042(10) 0.0010(11) C24 0.0457(16) 0.0274(15) 0.0522(17) -0.0025(12) 0.0337(14) 0.0027(13) N5 0.0389(13) 0.0522(15) 0.0398(13) 0.0040(11) 0.0107(10) -0.0006(12) C25 0.0246(13) 0.0259(13) 0.0204(12) -0.0009(10) 0.0060(10) -0.0054(11) C26 0.0304(14) 0.0306(14) 0.0309(13) 0.0018(11) 0.0164(11) 0.0042(12) C27 0.0260(13) 0.0340(15) 0.0284(13) 0.0001(11) 0.0065(11) 0.0050(12) C28 0.0238(13) 0.0252(14) 0.0264(13) 0.0039(10) 0.0066(10) 0.0012(11) C29 0.0285(14) 0.0248(14) 0.0322(14) -0.0019(11) 0.0060(11) -0.0003(11) C30 0.0252(14) 0.0417(16) 0.0305(13) -0.0091(12) 0.0099(11) 0.0024(12) O4 0.0221(9) 0.0463(11) 0.0309(9) 0.0120(8) 0.0135(7) 0.0091(8) O3 0.0185(8) 0.0524(11) 0.0207(8) -0.0014(7) 0.0071(7) -0.0017(8) C32 0.0181(12) 0.0303(14) 0.0222(12) -0.0018(10) 0.0067(10) -0.0004(11) N4 0.0361(13) 0.0502(15) 0.0359(12) -0.0064(10) 0.0121(10) -0.0039(11) C34 0.0240(13) 0.0243(14) 0.0266(13) -0.0038(10) 0.0063(11) 0.0013(11) C35 0.0247(13) 0.0230(13) 0.0235(12) 0.0042(10) 0.0058(10) 0.0007(11) C36 0.0269(13) 0.0266(14) 0.0190(11) -0.0014(10) 0.0088(10) -0.0041(11) C37 0.0176(12) 0.0280(14) 0.0222(12) -0.0053(10) 0.0066(10) -0.0080(11) C38 0.0198(12) 0.0215(13) 0.0217(12) -0.0056(10) 0.0068(9) -0.0039(10) C39 0.0268(13) 0.0249(13) 0.0224(12) -0.0002(10) 0.0091(10) 0.0013(11) C40 0.0227(13) 0.0289(14) 0.0221(12) -0.0008(10) 0.0104(10) 0.0028(11) C41 0.0202(13) 0.0223(13) 0.0286(13) -0.0037(10) 0.0050(10) 0.0007(11) C42 0.0256(14) 0.0281(14) 0.0258(13) -0.0080(11) 0.0046(11) -0.0067(11) C43 0.0211(13) 0.0253(13) 0.0253(13) 0.0006(10) 0.0097(10) -0.0009(11) C44 0.0275(13) 0.0204(13) 0.0310(13) 0.0006(10) 0.0156(11) 0.0025(11) C45 0.0288(14) 0.0325(14) 0.0266(13) 0.0019(11) 0.0149(11) 0.0085(12) C46 0.0161(12) 0.0340(14) 0.0189(12) -0.0051(10) 0.0060(10) -0.0057(11) C47 0.0214(13) 0.0237(13) 0.0276(13) 0.0087(10) 0.0097(10) 0.0039(11) C48 0.0240(14) 0.0332(15) 0.0259(13) -0.0019(11) 0.0095(10) -0.0026(12) C49 0.0284(13) 0.0224(13) 0.0271(13) 0.0017(10) 0.0163(10) 0.0012(11) C50 0.0261(13) 0.0219(13) 0.0237(12) 0.0010(10) 0.0077(10) -0.0013(11) C51 0.0197(12) 0.0208(13) 0.0248(12) 0.0059(10) 0.0078(10) 0.0006(10) C52 0.0269(13) 0.0303(14) 0.0234(12) 0.0021(10) 0.0084(10) -0.0032(11) C53 0.0238(13) 0.0354(15) 0.0189(12) 0.0023(10) 0.0050(10) -0.0046(12) C54 0.0231(13) 0.0284(14) 0.0263(12) 0.0024(10) 0.0093(10) 0.0074(11) C55 0.0201(12) 0.0245(13) 0.0251(12) -0.0030(10) 0.0048(10) -0.0010(11) C56 0.0222(13) 0.0248(13) 0.0223(12) -0.0015(10) 0.0074(10) -0.0014(11) C57 0.0264(14) 0.0306(15) 0.0265(13) 0.0047(11) 0.0115(11) 0.0019(12) C58 0.0176(12) 0.0301(14) 0.0204(12) 0.0047(10) 0.0063(10) -0.0012(11) C59 0.0271(13) 0.0261(14) 0.0213(12) -0.0031(10) 0.0067(10) -0.0089(11) C60 0.0198(12) 0.0292(14) 0.0262(12) -0.0012(11) 0.0032(10) -0.0017(11) N3 0.0329(12) 0.0457(14) 0.0376(12) 0.0046(10) 0.0130(10) 0.0043(11) C33 0.0275(14) 0.0318(15) 0.0309(14) -0.0032(11) 0.0169(11) -0.0004(12) C61 0.0311(15) 0.0438(17) 0.0349(14) -0.0100(12) 0.0230(12) -0.0080(13) O1 0.0219(9) 0.0440(11) 0.0392(10) -0.0158(8) 0.0090(7) -0.0067(8) C63 0.0292(14) 0.0228(13) 0.0207(12) -0.0009(10) 0.0064(10) -0.0017(11) C64 0.0225(13) 0.0253(13) 0.0230(12) 0.0021(10) 0.0082(10) 0.0039(11) C65 0.0304(15) 0.0275(15) 0.0339(14) 0.0005(11) 0.0094(12) -0.0043(12) C66 0.0218(13) 0.0304(14) 0.0314(14) -0.0088(11) 0.0074(11) -0.0054(11) C67 0.0261(13) 0.0205(13) 0.0206(12) -0.0018(10) 0.0062(10) -0.0014(11) N1 0.0322(12) 0.0354(13) 0.0353(12) -0.0053(10) 0.0144(9) -0.0096(10) C68 0.0313(14) 0.0253(14) 0.0225(12) -0.0008(10) 0.0121(11) -0.0040(12) C69 0.0215(13) 0.0269(13) 0.0246(12) 0.0003(10) 0.0068(10) 0.0019(11) C70 0.0245(13) 0.0229(13) 0.0313(13) -0.0016(11) 0.0089(10) -0.0031(11) C71 0.0194(13) 0.0293(14) 0.0217(12) 0.0015(10) 0.0027(10) -0.0024(11) C72 0.0220(13) 0.0243(13) 0.0198(12) 0.0024(10) 0.0072(10) -0.0042(11) C73 0.0316(14) 0.0263(14) 0.0316(13) 0.0030(11) 0.0127(11) -0.0016(12) C74 0.0269(13) 0.0245(14) 0.0354(14) 0.0053(11) 0.0077(11) 0.0027(11) C75 0.0338(15) 0.0392(17) 0.0435(16) -0.0037(12) 0.0179(13) -0.0036(13) C76 0.0296(14) 0.0418(17) 0.0274(14) -0.0004(12) -0.0006(11) 0.0070(12) C77 0.0344(14) 0.0404(16) 0.0252(13) 0.0013(11) 0.0111(11) -0.0005(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C16 1.373(2) . ? O2 C5 1.393(2) . ? O5 C3 1.384(2) . ? O5 C18 1.392(2) . ? C1 C19 1.390(3) . ? C1 C2 1.394(3) . ? C1 C6 1.440(3) . ? C2 C7 1.373(3) . ? C2 H2 0.9500 . ? C3 C14 1.379(3) . ? C3 C22 1.380(3) . ? C4 C5 1.378(3) . ? C4 C11 1.383(3) . ? C4 H4 0.9500 . ? C5 C25 1.378(3) . ? C6 N2 1.149(2) . ? C7 C16 1.385(3) . ? C7 H7 0.9500 . ? C8 C24 1.156(3) . ? C8 C10 1.444(3) . ? C9 C18 1.375(3) . ? C9 C23 1.383(3) . ? C9 H9 0.9500 . ? C10 C21 1.392(3) . ? C10 C23 1.392(3) . ? C11 C15 1.394(3) . ? C11 H11 0.9500 . ? C12 C25 1.388(3) . ? C12 C15 1.389(3) . ? C12 H12 0.9500 . ? C13 N5 1.155(2) . ? C13 C28 1.434(3) . ? C14 C26 1.381(3) . ? C14 H14 0.9500 . ? C15 C17 1.441(3) . ? C16 C20 1.385(3) . ? C17 C30 1.184(3) . ? C18 C27 1.379(3) . ? C19 C20 1.386(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C27 1.380(3) . ? C21 H21 0.9500 . ? C22 C29 1.376(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 C28 1.391(3) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? C28 C29 1.384(3) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? O4 C32 1.382(2) . ? O4 C47 1.386(2) . ? O3 C58 1.387(2) . ? O3 C46 1.388(2) . ? C32 C35 1.383(3) . ? C32 C54 1.384(3) . ? N4 C48 1.159(2) . ? C34 C33 1.159(3) . ? C34 C38 1.446(3) . ? C35 C41 1.377(3) . ? C35 H35 0.9500 . ? C36 C58 1.379(3) . ? C36 C49 1.381(3) . ? C36 H36 0.9500 . ? C37 C60 1.391(3) . ? C37 C59 1.397(3) . ? C37 C42 1.451(3) . ? C38 C39 1.394(3) . ? C38 C41 1.398(3) . ? C39 C54 1.376(3) . ? C39 H39 0.9500 . ? C40 C56 1.382(3) . ? C40 C58 1.387(3) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 C61 1.155(3) . ? C43 C44 1.385(3) . ? C43 C52 1.391(3) . ? C43 C48 1.431(3) . ? C44 C50 1.380(3) . ? C44 H44 0.9500 . ? C45 C47 1.376(3) . ? C45 C52 1.388(3) . ? C45 H45 0.9500 . ? C46 C53 1.378(3) . ? C46 C55 1.380(3) . ? C47 C50 1.378(3) . ? C49 C51 1.396(3) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? C51 C56 1.388(3) . ? C51 C57 1.437(3) . ? C52 H52 0.9500 . ? C53 C60 1.384(3) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? C55 C59 1.378(3) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C57 N3 1.157(2) . ? C59 H59 0.9500 . ? C60 H60 0.9500 . ? C33 H33 0.9500 . ? C61 H61 0.9500 . ? O1 C71 1.374(2) . ? O1 C66 1.402(2) . ? C63 C69 1.387(3) . ? C63 C72 1.388(3) . ? C63 H63 0.9500 . ? C64 C67 1.372(3) . ? C64 C72 1.401(3) . ? C64 H64 0.9500 . ? C65 C75 1.164(3) . ? C65 C70 1.447(3) . ? C66 C73 1.372(3) . ? C66 C76 1.374(3) . ? C67 C71 1.386(3) . ? C67 H67 0.9500 . ? N1 C68 1.150(2) . ? C68 C72 1.438(3) . ? C69 C71 1.385(3) . ? C69 H69 0.9500 . ? C70 C74 1.389(3) . ? C70 C77 1.391(3) . ? C73 C74 1.387(3) . ? C73 H73 0.9500 . ? C74 H74 0.9500 . ? C75 H75 0.9500 . ? C76 C77 1.380(3) . ? C76 H76 0.9500 . ? C77 H77 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 O2 C5 121.09(15) . . ? C3 O5 C18 120.43(16) . . ? C19 C1 C2 119.8(2) . . ? C19 C1 C6 120.88(19) . . ? C2 C1 C6 119.29(19) . . ? C7 C2 C1 119.9(2) . . ? C7 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C14 C3 C22 121.1(2) . . ? C14 C3 O5 115.6(2) . . ? C22 C3 O5 123.1(2) . . ? C5 C4 C11 119.4(2) . . ? C5 C4 H4 120.3 . . ? C11 C4 H4 120.3 . . ? C4 C5 C25 121.07(19) . . ? C4 C5 O2 121.89(19) . . ? C25 C5 O2 116.73(18) . . ? N2 C6 C1 177.9(2) . . ? C2 C7 C16 119.9(2) . . ? C2 C7 H7 120.1 . . ? C16 C7 H7 120.1 . . ? C24 C8 C10 177.1(3) . . ? C18 C9 C23 119.3(2) . . ? C18 C9 H9 120.3 . . ? C23 C9 H9 120.3 . . ? C21 C10 C23 118.7(2) . . ? C21 C10 C8 122.0(2) . . ? C23 C10 C8 119.3(2) . . ? C4 C11 C15 120.86(19) . . ? C4 C11 H11 119.6 . . ? C15 C11 H11 119.6 . . ? C25 C12 C15 120.8(2) . . ? C25 C12 H12 119.6 . . ? C15 C12 H12 119.6 . . ? N5 C13 C28 179.5(3) . . ? C3 C14 C26 119.5(2) . . ? C3 C14 H14 120.2 . . ? C26 C14 H14 120.2 . . ? C12 C15 C11 118.54(19) . . ? C12 C15 C17 121.57(19) . . ? C11 C15 C17 119.88(19) . . ? O2 C16 C7 115.42(18) . . ? O2 C16 C20 123.29(19) . . ? C7 C16 C20 121.0(2) . . ? C30 C17 C15 178.6(3) . . ? C9 C18 C27 121.3(2) . . ? C9 C18 O5 115.40(19) . . ? C27 C18 O5 123.04(19) . . ? C20 C19 C1 120.3(2) . . ? C20 C19 H19 119.8 . . ? C1 C19 H19 119.8 . . ? C16 C20 C19 119.0(2) . . ? C16 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C27 C21 C10 120.9(2) . . ? C27 C21 H21 119.5 . . ? C10 C21 H21 119.5 . . ? C29 C22 C3 119.2(2) . . ? C29 C22 H22 120.4 . . ? C3 C22 H22 120.4 . . ? C9 C23 C10 120.7(2) . . ? C9 C23 H23 119.7 . . ? C10 C23 H23 119.7 . . ? C8 C24 H24 180.0 . . ? C5 C25 C12 119.26(19) . . ? C5 C25 H25 120.4 . . ? C12 C25 H25 120.4 . . ? C14 C26 C28 119.9(2) . . ? C14 C26 H26 120.0 . . ? C28 C26 H26 120.0 . . ? C18 C27 C21 119.1(2) . . ? C18 C27 H27 120.4 . . ? C21 C27 H27 120.4 . . ? C29 C28 C26 119.6(2) . . ? C29 C28 C13 120.5(2) . . ? C26 C28 C13 119.9(2) . . ? C22 C29 C28 120.6(2) . . ? C22 C29 H29 119.7 . . ? C28 C29 H29 119.7 . . ? C17 C30 H30 180.0 . . ? C32 O4 C47 121.01(16) . . ? C58 O3 C46 120.86(15) . . ? O4 C32 C35 115.22(19) . . ? O4 C32 C54 123.63(19) . . ? C35 C32 C54 120.9(2) . . ? C33 C34 C38 177.3(2) . . ? C41 C35 C32 119.7(2) . . ? C41 C35 H35 120.2 . . ? C32 C35 H35 120.2 . . ? C58 C36 C49 119.55(19) . . ? C58 C36 H36 120.2 . . ? C49 C36 H36 120.2 . . ? C60 C37 C59 118.9(2) . . ? C60 C37 C42 120.5(2) . . ? C59 C37 C42 120.6(2) . . ? C39 C38 C41 118.6(2) . . ? C39 C38 C34 119.55(19) . . ? C41 C38 C34 121.8(2) . . ? C54 C39 C38 121.1(2) . . ? C54 C39 H39 119.5 . . ? C38 C39 H39 119.5 . . ? C56 C40 C58 118.8(2) . . ? C56 C40 H40 120.6 . . ? C58 C40 H40 120.6 . . ? C35 C41 C38 120.5(2) . . ? C35 C41 H41 119.7 . . ? C38 C41 H41 119.7 . . ? C61 C42 C37 178.0(3) . . ? C44 C43 C52 119.81(19) . . ? C44 C43 C48 119.9(2) . . ? C52 C43 C48 120.32(19) . . ? C50 C44 C43 120.1(2) . . ? C50 C44 H44 119.9 . . ? C43 C44 H44 119.9 . . ? C47 C45 C52 119.0(2) . . ? C47 C45 H45 120.5 . . ? C52 C45 H45 120.5 . . ? C53 C46 C55 121.5(2) . . ? C53 C46 O3 116.25(19) . . ? C55 C46 O3 121.9(2) . . ? C45 C47 C50 121.4(2) . . ? C45 C47 O4 122.9(2) . . ? C50 C47 O4 115.36(19) . . ? N4 C48 C43 179.2(2) . . ? C36 C49 C51 119.6(2) . . ? C36 C49 H49 120.2 . . ? C51 C49 H49 120.2 . . ? C47 C50 C44 119.5(2) . . ? C47 C50 H50 120.2 . . ? C44 C50 H50 120.2 . . ? C56 C51 C49 120.12(19) . . ? C56 C51 C57 120.13(19) . . ? C49 C51 C57 119.7(2) . . ? C45 C52 C43 120.1(2) . . ? C45 C52 H52 119.9 . . ? C43 C52 H52 119.9 . . ? C46 C53 C60 119.2(2) . . ? C46 C53 H53 120.4 . . ? C60 C53 H53 120.4 . . ? C39 C54 C32 119.2(2) . . ? C39 C54 H54 120.4 . . ? C32 C54 H54 120.4 . . ? C59 C55 C46 119.0(2) . . ? C59 C55 H55 120.5 . . ? C46 C55 H55 120.5 . . ? C40 C56 C51 120.33(19) . . ? C40 C56 H56 119.8 . . ? C51 C56 H56 119.8 . . ? N3 C57 C51 178.7(3) . . ? C36 C58 O3 115.10(18) . . ? C36 C58 C40 121.58(19) . . ? O3 C58 C40 123.09(19) . . ? C55 C59 C37 120.8(2) . . ? C55 C59 H59 119.6 . . ? C37 C59 H59 119.6 . . ? C53 C60 C37 120.6(2) . . ? C53 C60 H60 119.7 . . ? C37 C60 H60 119.7 . . ? C34 C33 H33 180.0 . . ? C42 C61 H61 180.0 . . ? C71 O1 C66 119.90(16) . . ? C69 C63 C72 120.4(2) . . ? C69 C63 H63 119.8 . . ? C72 C63 H63 119.8 . . ? C67 C64 C72 120.1(2) . . ? C67 C64 H64 119.9 . . ? C72 C64 H64 119.9 . . ? C75 C65 C70 178.4(3) . . ? C73 C66 C76 121.4(2) . . ? C73 C66 O1 117.8(2) . . ? C76 C66 O1 120.5(2) . . ? C64 C67 C71 119.5(2) . . ? C64 C67 H67 120.3 . . ? C71 C67 H67 120.3 . . ? N1 C68 C72 178.1(2) . . ? C71 C69 C63 118.8(2) . . ? C71 C69 H69 120.6 . . ? C63 C69 H69 120.6 . . ? C74 C70 C77 118.9(2) . . ? C74 C70 C65 121.0(2) . . ? C77 C70 C65 120.0(2) . . ? O1 C71 C69 123.5(2) . . ? O1 C71 C67 114.89(19) . . ? C69 C71 C67 121.5(2) . . ? C63 C72 C64 119.67(19) . . ? C63 C72 C68 121.02(19) . . ? C64 C72 C68 119.3(2) . . ? C66 C73 C74 118.9(2) . . ? C66 C73 H73 120.6 . . ? C74 C73 H73 120.6 . . ? C73 C74 C70 120.9(2) . . ? C73 C74 H74 119.6 . . ? C70 C74 H74 119.6 . . ? C65 C75 H75 180.0 . . ? C66 C76 C77 119.8(2) . . ? C66 C76 H76 120.1 . . ? C77 C76 H76 120.1 . . ? C76 C77 C70 120.2(2) . . ? C76 C77 H77 119.9 . . ? C70 C77 H77 119.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.212 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.038 # END# data_11 _database_code_depnum_ccdc_archive 'CCDC 265006' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-Bromophenoxy)benzonitrile ; _chemical_name_common 4-(4-Bromophenoxy)benzonitrile _chemical_melting_point 347 _chemical_formula_moiety 'C13 H8 Br N O' _chemical_formula_sum 'C13 H8 Br N O' _chemical_formula_weight 274.11 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.3919(18) _cell_length_b 7.3765(11) _cell_length_c 11.9824(18) _cell_angle_alpha 90.00 _cell_angle_beta 98.842(2) _cell_angle_gamma 90.00 _cell_volume 1082.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5415 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 26.03 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 3.772 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3138 _exptl_absorpt_correction_T_max 0.3974 _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7741 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.04 _reflns_number_total 2135 _reflns_number_gt 1898 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.7992P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2135 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.264 _refine_ls_restrained_S_all 1.264 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.64931(16) 0.0697(3) 0.54181(15) 0.0301(5) Uani 1 1 d . . . C6 C 0.9239(2) 0.2089(4) 0.6762(2) 0.0262(6) Uani 1 1 d . B . H6 H 0.9874 0.2680 0.6590 0.031 Uiso 1 1 calc R . . C5 C 0.8353(2) 0.1801(4) 0.5926(2) 0.0264(6) Uani 1 1 d . . . H5 H 0.8373 0.2209 0.5178 0.032 Uiso 1 1 calc R . . C1 C 0.9189(2) 0.1502(4) 0.7855(2) 0.0229(6) Uani 1 1 d . . . C4 C 0.7444(2) 0.0922(4) 0.6182(2) 0.0234(6) Uani 1 1 d . B . C2 C 0.8276(2) 0.0621(4) 0.8117(2) 0.0250(6) Uani 1 1 d . B . H2 H 0.8254 0.0209 0.8864 0.030 Uiso 1 1 calc R . . C3 C 0.7392(2) 0.0347(4) 0.7274(2) 0.0246(6) Uani 1 1 d . . . H3 H 0.6752 -0.0234 0.7443 0.030 Uiso 1 1 calc R B . C9 C 0.6480(2) 0.0014(4) 0.1987(2) 0.0245(6) Uani 1 1 d . . . C10 C 0.5651(2) 0.0977(4) 0.2385(2) 0.0296(7) Uani 1 1 d . A . H10 H 0.5065 0.1473 0.1870 0.036 Uiso 1 1 calc R . . C8 C 0.7340(2) -0.0703(4) 0.2734(2) 0.0291(6) Uani 1 1 d . A . H8 H 0.7907 -0.1345 0.2456 0.035 Uiso 1 1 calc R . . C7 C 0.7369(3) -0.0478(4) 0.3892(2) 0.0318(7) Uani 1 1 d . . . H7 H 0.7949 -0.0980 0.4411 0.038 Uiso 1 1 calc R A . C11 C 0.5687(2) 0.1207(4) 0.3535(2) 0.0258(6) Uani 1 1 d . . . H11 H 0.5125 0.1859 0.3817 0.031 Uiso 1 1 calc R A . C12 C 0.6545(2) 0.0484(4) 0.4272(2) 0.0248(6) Uani 1 1 d . A . C13 C 0.6479(6) -0.0186(10) 0.0923(5) 0.0235(16) Uani 0.53 1 d P A 1 N1 N 0.6474(9) -0.0498(15) -0.0143(6) 0.050(2) Uani 0.70 1 d P A 1 C14 C 1.0063(15) 0.192(4) 0.880(2) 0.055(7) Uani 0.46 1 d P B 1 N2 N 1.0767(17) 0.195(3) 0.9398(18) 0.066(7) Uani 0.30 1 d P B 1 Br2 Br 1.04253(8) 0.19866(15) 0.90235(9) 0.0249(2) Uani 0.70 1 d P B 2 Br1 Br 0.64413(18) -0.0431(3) 0.03340(18) 0.0367(5) Uani 0.30 1 d P A 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0210(11) 0.0458(13) 0.0247(9) 0.0045(9) 0.0077(8) 0.0027(9) C6 0.0248(15) 0.0240(14) 0.0319(14) 0.0043(12) 0.0115(12) 0.0001(12) C5 0.0266(16) 0.0296(16) 0.0251(12) 0.0082(11) 0.0105(11) 0.0033(12) C1 0.0234(15) 0.0216(14) 0.0244(12) -0.0033(10) 0.0061(11) 0.0023(11) C4 0.0228(15) 0.0231(14) 0.0256(13) 0.0022(10) 0.0078(11) 0.0057(11) C2 0.0308(16) 0.0239(14) 0.0233(12) -0.0006(11) 0.0134(11) 0.0012(12) C3 0.0249(16) 0.0230(14) 0.0290(13) -0.0011(11) 0.0137(12) -0.0015(12) C9 0.0253(16) 0.0227(14) 0.0273(13) -0.0004(10) 0.0092(12) -0.0056(12) C10 0.0239(16) 0.0315(16) 0.0333(15) 0.0012(12) 0.0042(12) -0.0036(13) C8 0.0259(16) 0.0273(15) 0.0365(15) 0.0005(12) 0.0130(12) 0.0023(12) C7 0.0292(17) 0.0324(16) 0.0336(15) 0.0079(13) 0.0045(13) 0.0077(13) C11 0.0178(14) 0.0308(15) 0.0295(13) 0.0007(11) 0.0056(11) 0.0013(12) C12 0.0229(15) 0.0271(15) 0.0261(13) 0.0046(11) 0.0091(11) -0.0033(12) C13 0.028(3) 0.035(3) 0.008(3) -0.014(3) 0.004(3) -0.002(2) N1 0.045(3) 0.059(3) 0.048(5) -0.010(4) 0.014(4) -0.004(2) C14 0.048(14) 0.067(11) 0.060(14) 0.023(9) 0.036(10) 0.021(10) N2 0.046(12) 0.076(11) 0.072(15) 0.026(11) -0.003(9) 0.013(9) Br2 0.0210(7) 0.0326(4) 0.0216(4) -0.0062(4) 0.0051(4) -0.0050(5) Br1 0.0297(7) 0.0383(8) 0.0435(14) -0.0022(12) 0.0100(13) -0.0085(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.386(3) . ? O1 C12 1.394(3) . ? C6 C5 1.384(4) . ? C6 C1 1.391(4) . ? C6 H6 0.9500 . ? C5 C4 1.375(4) . ? C5 H5 0.9500 . ? C1 C2 1.382(4) . ? C1 C14 1.476(19) . ? C1 Br2 1.943(3) . ? C4 C3 1.386(4) . ? C2 C3 1.386(4) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C9 C13 1.284(7) . ? C9 C8 1.386(4) . ? C9 C10 1.392(4) . ? C9 Br1 2.001(3) . ? C10 C11 1.383(4) . ? C10 H10 0.9500 . ? C8 C7 1.392(4) . ? C8 H8 0.9500 . ? C7 C12 1.377(4) . ? C7 H7 0.9500 . ? C11 C12 1.381(4) . ? C11 H11 0.9500 . ? C13 N1 1.297(7) . ? C14 N2 1.04(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C12 120.1(2) . . ? C5 C6 C1 119.3(3) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C4 C5 C6 119.8(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C2 C1 C6 121.1(3) . . ? C2 C1 C14 117.1(10) . . ? C6 C1 C14 121.6(10) . . ? C2 C1 Br2 120.4(2) . . ? C6 C1 Br2 118.5(2) . . ? C14 C1 Br2 4.7(10) . . ? C5 C4 C3 120.9(3) . . ? C5 C4 O1 123.4(2) . . ? C3 C4 O1 115.4(2) . . ? C1 C2 C3 119.1(2) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C13 C9 C8 118.7(4) . . ? C13 C9 C10 120.7(4) . . ? C8 C9 C10 120.6(3) . . ? C13 C9 Br1 3.1(3) . . ? C8 C9 Br1 118.4(2) . . ? C10 C9 Br1 121.0(2) . . ? C11 C10 C9 119.4(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C12 C7 C8 118.9(3) . . ? C12 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C7 C12 C11 121.7(3) . . ? C7 C12 O1 122.2(2) . . ? C11 C12 O1 116.0(3) . . ? C9 C13 N1 176.3(10) . . ? N2 C14 C1 166(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.233 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.060 # END# data_12 _database_code_depnum_ccdc_archive 'CCDC 265007' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Aniline, N,N-dimethyl-p-(p-nitrophenoxy) ; _chemical_name_common 'Aniline, N,N-dimethyl-p-(p-nitrophenoxy)' _chemical_melting_point 216 _chemical_formula_moiety 'C14 H14 N2 O3' _chemical_formula_sum 'C14 H14 N2 O3' _chemical_formula_weight 258.27 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 5.8340(9) _cell_length_b 28.698(4) _cell_length_c 7.6833(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.208(2) _cell_angle_gamma 90.00 _cell_volume 1286.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5134 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 26.01 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11727 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 26.07 _reflns_number_total 2547 _reflns_number_gt 1852 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.0650P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2547 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0662 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1331 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.66453(18) 0.24800(3) 0.18053(15) 0.0559(3) Uani 1 1 d . . . C1 C 0.6767(3) 0.16901(5) 0.1158(2) 0.0513(4) Uani 1 1 d . . . H1 H 0.5401 0.1730 0.0548 0.062 Uiso 1 1 calc R . . C2 C 0.9819(3) 0.30063(5) 0.1177(2) 0.0490(4) Uani 1 1 d . . . H2 H 1.0592 0.2773 0.0576 0.059 Uiso 1 1 calc R . . C3 C 0.9821(3) 0.20132(5) 0.2889(2) 0.0484(4) Uani 1 1 d . . . H3 H 1.0501 0.2268 0.3435 0.058 Uiso 1 1 calc R . . C4 C 1.0806(3) 0.15774(5) 0.3003(2) 0.0503(4) Uani 1 1 d . . . H4 H 1.2159 0.1535 0.3627 0.060 Uiso 1 1 calc R . . C5 C 0.6647(3) 0.32526(5) 0.2873(2) 0.0500(4) Uani 1 1 d . . . H5 H 0.5271 0.3186 0.3428 0.060 Uiso 1 1 calc R . . C6 C 1.0715(2) 0.34492(5) 0.1249(2) 0.0488(4) Uani 1 1 d . . . H6 H 1.2097 0.3511 0.0695 0.059 Uiso 1 1 calc R . . C7 C 0.7751(3) 0.12578(6) 0.1268(2) 0.0542(4) Uani 1 1 d . . . H7 H 0.7066 0.1003 0.0732 0.065 Uiso 1 1 calc R . . C8 C 0.7528(3) 0.36978(6) 0.2939(2) 0.0507(4) Uani 1 1 d . . . H8 H 0.6727 0.3928 0.3532 0.061 Uiso 1 1 calc R . . C9 C 0.9602(3) 0.38105(5) 0.21333(19) 0.0456(4) Uani 1 1 d . . . N1 N 1.0531(2) 0.42528(4) 0.22429(19) 0.0590(4) Uani 1 1 d . . . C10 C 0.7781(2) 0.29075(5) 0.19946(19) 0.0445(4) Uani 1 1 d . . . C11 C 0.9775(3) 0.12063(5) 0.2188(2) 0.0485(4) Uani 1 1 d . . . N2 N 1.0854(3) 0.07497(5) 0.2293(2) 0.0664(4) Uani 1 1 d . . . C12 C 0.7802(2) 0.20672(5) 0.19514(19) 0.0435(4) Uani 1 1 d . . . O2 O 0.9957(3) 0.04253(5) 0.1548(2) 0.1016(6) Uani 1 1 d . . . C13 C 1.2357(3) 0.43842(6) 0.1068(3) 0.0771(6) Uani 1 1 d . . . H13A H 1.3598 0.4167 0.1175 0.116 Uiso 1 1 calc R . . H13B H 1.2890 0.4691 0.1357 0.116 Uiso 1 1 calc R . . H13C H 1.1791 0.4382 -0.0107 0.116 Uiso 1 1 calc R . . O3 O 1.2631(3) 0.07115(5) 0.3102(3) 0.1142(7) Uani 1 1 d . . . C14 C 0.9137(4) 0.46321(6) 0.2875(3) 0.0874(7) Uani 1 1 d . . . H14A H 0.7820 0.4669 0.2134 0.131 Uiso 1 1 calc R . . H14B H 1.0018 0.4915 0.2870 0.131 Uiso 1 1 calc R . . H14C H 0.8646 0.4565 0.4039 0.131 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0494(6) 0.0449(7) 0.0735(8) 0.0056(5) -0.0108(5) -0.0013(5) C1 0.0485(9) 0.0536(10) 0.0516(10) 0.0006(7) -0.0051(7) -0.0105(7) C2 0.0515(9) 0.0433(8) 0.0522(9) -0.0020(7) 0.0042(7) 0.0064(7) C3 0.0565(9) 0.0417(8) 0.0470(9) -0.0037(7) -0.0095(7) -0.0036(7) C4 0.0535(9) 0.0471(9) 0.0503(9) 0.0001(7) -0.0079(7) 0.0004(7) C5 0.0469(8) 0.0547(10) 0.0485(9) 0.0081(7) 0.0031(7) 0.0064(7) C6 0.0460(8) 0.0479(9) 0.0525(10) 0.0021(7) 0.0046(7) 0.0011(7) C7 0.0600(10) 0.0494(9) 0.0532(10) -0.0071(8) 0.0026(8) -0.0164(8) C8 0.0589(9) 0.0461(9) 0.0472(9) -0.0008(7) 0.0046(7) 0.0108(7) C9 0.0537(9) 0.0425(9) 0.0406(8) 0.0029(6) -0.0061(7) 0.0040(7) N1 0.0735(9) 0.0410(8) 0.0625(9) -0.0031(6) 0.0008(7) -0.0027(7) C10 0.0468(8) 0.0406(8) 0.0460(8) 0.0054(7) -0.0077(7) 0.0023(6) C11 0.0565(9) 0.0395(8) 0.0496(9) 0.0005(7) 0.0085(7) -0.0010(7) N2 0.0778(11) 0.0431(9) 0.0783(11) -0.0030(7) 0.0102(9) 0.0023(8) C12 0.0472(8) 0.0432(8) 0.0403(8) 0.0043(6) 0.0020(6) -0.0040(6) O2 0.1166(12) 0.0456(8) 0.1426(15) -0.0218(9) -0.0073(10) -0.0034(8) C13 0.0718(12) 0.0529(11) 0.1067(17) 0.0035(10) 0.0082(11) -0.0119(9) O3 0.1111(12) 0.0661(10) 0.1650(18) -0.0150(10) -0.0444(12) 0.0318(9) C14 0.1090(16) 0.0459(11) 0.1073(18) -0.0142(11) 0.0212(13) -0.0033(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C12 1.3678(17) . ? O1 C10 1.4017(17) . ? C1 C7 1.369(2) . ? C1 C12 1.380(2) . ? C1 H1 0.9300 . ? C2 C6 1.375(2) . ? C2 C10 1.376(2) . ? C2 H2 0.9300 . ? C3 C4 1.379(2) . ? C3 C12 1.387(2) . ? C3 H3 0.9300 . ? C4 C11 1.373(2) . ? C4 H4 0.9300 . ? C5 C10 1.370(2) . ? C5 C8 1.378(2) . ? C5 H5 0.9300 . ? C6 C9 1.400(2) . ? C6 H6 0.9300 . ? C7 C11 1.382(2) . ? C7 H7 0.9300 . ? C8 C9 1.399(2) . ? C8 H8 0.9300 . ? C9 N1 1.3825(19) . ? N1 C14 1.444(2) . ? N1 C13 1.449(2) . ? C11 N2 1.456(2) . ? N2 O2 1.2110(19) . ? N2 O3 1.212(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 C10 121.11(11) . . ? C7 C1 C12 120.03(15) . . ? C7 C1 H1 120.0 . . ? C12 C1 H1 120.0 . . ? C6 C2 C10 120.05(14) . . ? C6 C2 H2 120.0 . . ? C10 C2 H2 120.0 . . ? C4 C3 C12 119.14(14) . . ? C4 C3 H3 120.4 . . ? C12 C3 H3 120.4 . . ? C11 C4 C3 119.54(14) . . ? C11 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C10 C5 C8 120.50(14) . . ? C10 C5 H5 119.8 . . ? C8 C5 H5 119.8 . . ? C2 C6 C9 121.81(14) . . ? C2 C6 H6 119.1 . . ? C9 C6 H6 119.1 . . ? C1 C7 C11 119.06(14) . . ? C1 C7 H7 120.5 . . ? C11 C7 H7 120.5 . . ? C5 C8 C9 121.39(14) . . ? C5 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? N1 C9 C8 121.64(14) . . ? N1 C9 C6 121.81(14) . . ? C8 C9 C6 116.53(14) . . ? C9 N1 C14 119.44(14) . . ? C9 N1 C13 119.34(14) . . ? C14 N1 C13 115.43(14) . . ? C5 C10 C2 119.70(14) . . ? C5 C10 O1 117.04(13) . . ? C2 C10 O1 122.82(13) . . ? C4 C11 C7 121.47(14) . . ? C4 C11 N2 118.99(15) . . ? C7 C11 N2 119.54(15) . . ? O2 N2 O3 122.72(16) . . ? O2 N2 C11 118.68(17) . . ? O3 N2 C11 118.60(15) . . ? O1 C12 C1 115.34(13) . . ? O1 C12 C3 123.85(13) . . ? C1 C12 C3 120.75(14) . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.158 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.054 # END# data_13 _database_code_depnum_ccdc_archive 'CCDC 265008' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-Dinitrodiphenyl ether ; _chemical_name_common "4,4'-Dinitrodiphenyl ether" _chemical_melting_point 418 _chemical_formula_moiety 'C12 H8 N2 O5' _chemical_formula_sum 'C12 H8 N2 O5' _chemical_formula_weight 260.20 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.4081(17) _cell_length_b 9.2706(17) _cell_length_c 9.8031(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.614(2) _cell_angle_gamma 90.00 _cell_volume 1124.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3409 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 25.98 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9526 _exptl_absorpt_correction_T_max 0.9783 _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5009 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 26.08 _reflns_number_total 1113 _reflns_number_gt 1010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.4631P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1113 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0973 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5000 0.04339(12) 0.7500 0.0273(3) Uani 1 2 d S . . C3 C 0.37220(10) 0.05813(13) 0.55928(13) 0.0252(3) Uani 1 1 d . . . H3 H 0.3397 -0.0275 0.5899 0.030 Uiso 1 1 calc R . . N1 N 0.33832(8) 0.32211(11) 0.27357(10) 0.0255(3) Uani 1 1 d . . . O2 O 0.36978(7) 0.44551(10) 0.25321(9) 0.0320(3) Uani 1 1 d . . . C2 C 0.33241(9) 0.12292(13) 0.43874(13) 0.0248(3) Uani 1 1 d . . . H2 H 0.2729 0.0825 0.3848 0.030 Uiso 1 1 calc R . . C1 C 0.38157(9) 0.24868(12) 0.39845(11) 0.0221(3) Uani 1 1 d . . . C6 C 0.46994(9) 0.30854(12) 0.47263(12) 0.0228(3) Uani 1 1 d . . . H6 H 0.5027 0.3937 0.4414 0.027 Uiso 1 1 calc R . . C4 C 0.45981(10) 0.11856(12) 0.63537(12) 0.0225(3) Uani 1 1 d . . . C5 C 0.51000(10) 0.24308(12) 0.59261(12) 0.0235(3) Uani 1 1 d . . . H5 H 0.5707 0.2823 0.6451 0.028 Uiso 1 1 calc R . . O3 O 0.27285(7) 0.25818(10) 0.19490(9) 0.0356(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0370(7) 0.0203(6) 0.0246(7) 0.000 0.0022(5) 0.000 C3 0.0265(6) 0.0202(6) 0.0299(7) -0.0053(5) 0.0092(5) -0.0028(4) N1 0.0219(5) 0.0303(6) 0.0244(5) -0.0058(4) 0.0016(4) 0.0051(4) O2 0.0340(5) 0.0283(5) 0.0329(5) 0.0027(4) -0.0020(4) 0.0041(4) C2 0.0198(6) 0.0268(6) 0.0281(6) -0.0096(5) 0.0027(5) -0.0016(4) C1 0.0206(6) 0.0243(6) 0.0216(6) -0.0056(5) 0.0026(5) 0.0041(4) C6 0.0240(6) 0.0202(6) 0.0247(6) -0.0027(4) 0.0041(5) -0.0009(4) C4 0.0248(6) 0.0212(6) 0.0220(6) -0.0024(4) 0.0052(5) 0.0029(4) C5 0.0217(6) 0.0239(6) 0.0248(6) -0.0039(5) 0.0005(5) -0.0030(4) O3 0.0312(5) 0.0440(6) 0.0297(5) -0.0093(4) -0.0085(4) 0.0011(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.3809(13) . ? O1 C4 1.3809(13) 2_656 ? C3 C2 1.3810(18) . ? C3 C4 1.3862(17) . ? C3 H3 0.9500 . ? N1 O3 1.2269(13) . ? N1 O2 1.2302(14) . ? N1 C1 1.4644(15) . ? C2 C1 1.3878(17) . ? C2 H2 0.9500 . ? C1 C6 1.3823(16) . ? C6 C5 1.3801(17) . ? C6 H6 0.9500 . ? C4 C5 1.3922(17) . ? C5 H5 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C4 119.39(13) . 2_656 ? C2 C3 C4 119.71(11) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? O3 N1 O2 123.36(11) . . ? O3 N1 C1 118.72(10) . . ? O2 N1 C1 117.92(9) . . ? C3 C2 C1 118.28(11) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C6 C1 C2 122.40(11) . . ? C6 C1 N1 118.36(10) . . ? C2 C1 N1 119.24(10) . . ? C5 C6 C1 119.20(11) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? O1 C4 C3 116.76(10) . . ? O1 C4 C5 121.50(11) . . ? C3 C4 C5 121.57(11) . . ? C6 C5 C4 118.82(11) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.175 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.055 # END# data_14 _database_code_depnum_ccdc_archive 'CCDC 265009' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-methyl-4'-nitrodiphenylether ; _chemical_name_common 4-methyl-4'-nitrodiphenylether _chemical_melting_point 343 _chemical_formula_moiety 'C13 H11 N O3' _chemical_formula_sum 'C13 H11 N O3' _chemical_formula_weight 229.23 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6100(11) _cell_length_b 8.8817(13) _cell_length_c 16.410(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.682(2) _cell_angle_gamma 90.00 _cell_volume 1105.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3724 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 26.05 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9766 _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5715 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 26.05 _reflns_number_total 2186 _reflns_number_gt 1907 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.2830P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2186 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0969 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O -0.01054(12) 0.34879(10) 0.27199(5) 0.0270(2) Uani 1 1 d . . . O1 O -0.37284(12) 0.70250(11) 0.53948(6) 0.0317(3) Uani 1 1 d . . . N1 N -0.22452(13) 0.72289(12) 0.51641(6) 0.0238(3) Uani 1 1 d . . . O2 O -0.12343(12) 0.82071(11) 0.54548(6) 0.0307(3) Uani 1 1 d . . . C2 C -0.00342(16) 0.65278(14) 0.42371(7) 0.0211(3) Uani 1 1 d . . . H2 H 0.0681 0.7333 0.4454 0.025 Uiso 1 1 calc R . . C4 C -0.05360(16) 0.44486(14) 0.33221(7) 0.0214(3) Uani 1 1 d . . . C1 C -0.16575(16) 0.62609(14) 0.45238(7) 0.0207(3) Uani 1 1 d . . . C8 C 0.16296(17) 0.47904(15) 0.17745(8) 0.0248(3) Uani 1 1 d . . . H8 H 0.0693 0.5479 0.1646 0.030 Uiso 1 1 calc R . . C7 C 0.14860(16) 0.36902(14) 0.23597(7) 0.0225(3) Uani 1 1 d . . . C11 C 0.43493(17) 0.27703(15) 0.21493(8) 0.0248(3) Uani 1 1 d . . . H11 H 0.5275 0.2071 0.2278 0.030 Uiso 1 1 calc R . . C5 C -0.21663(16) 0.41854(15) 0.36229(8) 0.0235(3) Uani 1 1 d . . . H5 H -0.2883 0.3377 0.3412 0.028 Uiso 1 1 calc R . . C12 C 0.28355(16) 0.26820(15) 0.25571(7) 0.0241(3) Uani 1 1 d . . . H12 H 0.2724 0.1940 0.2967 0.029 Uiso 1 1 calc R . . C10 C 0.45511(17) 0.38590(14) 0.15544(7) 0.0237(3) Uani 1 1 d . . . C9 C 0.31711(17) 0.48704(14) 0.13779(8) 0.0243(3) Uani 1 1 d . . . H9 H 0.3288 0.5630 0.0978 0.029 Uiso 1 1 calc R . . C3 C 0.05450(16) 0.56139(14) 0.36315(7) 0.0212(3) Uani 1 1 d . . . H3 H 0.1664 0.5779 0.3430 0.025 Uiso 1 1 calc R . . C6 C -0.27390(16) 0.50949(15) 0.42243(7) 0.0231(3) Uani 1 1 d . . . H6 H -0.3853 0.4929 0.4431 0.028 Uiso 1 1 calc R . . C13 C 0.61945(18) 0.39063(17) 0.11033(9) 0.0310(3) Uani 1 1 d . . . H13A H 0.7232 0.3799 0.1494 0.046 Uiso 1 1 calc R . . H13B H 0.6253 0.4870 0.0816 0.046 Uiso 1 1 calc R . . H13C H 0.6168 0.3081 0.0706 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0281(5) 0.0254(5) 0.0287(5) -0.0086(4) 0.0092(4) -0.0059(4) O1 0.0270(5) 0.0383(6) 0.0311(5) -0.0023(4) 0.0106(4) 0.0017(4) N1 0.0258(6) 0.0246(6) 0.0210(5) 0.0023(5) 0.0018(4) 0.0042(4) O2 0.0329(5) 0.0290(5) 0.0302(5) -0.0084(4) 0.0024(4) -0.0010(4) C2 0.0245(6) 0.0181(6) 0.0203(6) 0.0022(5) -0.0006(5) -0.0009(5) C4 0.0267(6) 0.0184(6) 0.0192(6) 0.0005(5) 0.0016(5) 0.0014(5) C1 0.0244(6) 0.0199(6) 0.0180(6) 0.0017(5) 0.0017(5) 0.0039(5) C8 0.0287(7) 0.0195(7) 0.0260(6) -0.0028(5) 0.0010(5) 0.0033(5) C7 0.0254(6) 0.0215(6) 0.0208(6) -0.0061(5) 0.0038(5) -0.0034(5) C11 0.0262(6) 0.0212(7) 0.0259(6) -0.0033(5) -0.0036(5) 0.0032(5) C5 0.0246(6) 0.0196(7) 0.0260(6) 0.0003(5) 0.0002(5) -0.0034(5) C12 0.0318(7) 0.0204(7) 0.0196(6) -0.0002(5) -0.0014(5) -0.0031(5) C10 0.0255(6) 0.0224(7) 0.0232(6) -0.0062(5) 0.0016(5) -0.0031(5) C9 0.0326(7) 0.0184(6) 0.0222(6) 0.0004(5) 0.0035(5) -0.0019(5) C3 0.0211(6) 0.0213(7) 0.0215(6) 0.0020(5) 0.0038(5) -0.0011(5) C6 0.0213(6) 0.0247(7) 0.0234(6) 0.0037(5) 0.0034(5) -0.0005(5) C13 0.0281(7) 0.0316(8) 0.0339(7) -0.0057(6) 0.0066(6) -0.0031(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C4 1.3656(15) . ? O3 C7 1.4019(15) . ? O1 N1 1.2329(14) . ? N1 O2 1.2306(14) . ? N1 C1 1.4560(16) . ? C2 C1 1.3779(17) . ? C2 C3 1.3828(17) . ? C2 H2 0.9500 . ? C4 C5 1.3919(18) . ? C4 C3 1.3920(17) . ? C1 C6 1.3876(18) . ? C8 C7 1.3807(18) . ? C8 C9 1.3889(18) . ? C8 H8 0.9500 . ? C7 C12 1.3810(18) . ? C11 C12 1.3809(18) . ? C11 C10 1.3914(19) . ? C11 H11 0.9500 . ? C5 C6 1.3736(18) . ? C5 H5 0.9500 . ? C12 H12 0.9500 . ? C10 C9 1.3943(18) . ? C10 C13 1.5050(18) . ? C9 H9 0.9500 . ? C3 H3 0.9500 . ? C6 H6 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O3 C7 119.45(9) . . ? O2 N1 O1 122.94(11) . . ? O2 N1 C1 118.52(10) . . ? O1 N1 C1 118.54(11) . . ? C1 C2 C3 119.45(11) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? O3 C4 C5 115.16(11) . . ? O3 C4 C3 123.99(11) . . ? C5 C4 C3 120.86(12) . . ? C2 C1 C6 122.00(12) . . ? C2 C1 N1 118.79(11) . . ? C6 C1 N1 119.21(11) . . ? C7 C8 C9 118.68(12) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C8 C7 C12 121.50(12) . . ? C8 C7 O3 120.27(11) . . ? C12 C7 O3 118.00(11) . . ? C12 C11 C10 121.58(12) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C6 C5 C4 120.02(12) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C11 C12 C7 118.91(12) . . ? C11 C12 H12 120.5 . . ? C7 C12 H12 120.5 . . ? C11 C10 C9 117.97(12) . . ? C11 C10 C13 120.55(12) . . ? C9 C10 C13 121.46(12) . . ? C8 C9 C10 121.36(12) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C2 C3 C4 119.02(12) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C6 C1 118.66(12) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.170 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.049 # END# data_15 _database_code_depnum_ccdc_archive 'CCDC 265010' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-Methylphenoxy)aniline ; _chemical_name_common 4-(4-Methylphenoxy)aniline _chemical_melting_point 390 _chemical_formula_moiety 'C13 H13 N O' _chemical_formula_sum 'C13 H13 N O' _chemical_formula_weight 199.24 _chemical_absolute_configuration 'unk ' 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.8600(11) _cell_length_b 7.8153(15) _cell_length_c 23.130(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1059.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4965 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 26.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9602 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1244 _reflns_number_gt 1115 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+0.1785P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1244 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1028 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5785(3) 0.5569(2) 0.10106(7) 0.0568(5) Uani 1 1 d . . . C1 C 0.7220(4) 1.0606(3) 0.05321(10) 0.0450(6) Uani 1 1 d . . . C2 C 0.8684(4) 0.9269(3) 0.04053(10) 0.0478(6) Uani 1 1 d . . . H2 H 1.0022 0.9490 0.0203 0.057 Uiso 1 1 calc R . . C3 C 0.4357(4) 0.5266(3) 0.14835(10) 0.0444(6) Uani 1 1 d . . . C4 C 0.5229(5) 1.0231(3) 0.08286(10) 0.0503(7) Uani 1 1 d . . . H4 H 0.4213 1.1108 0.0916 0.060 Uiso 1 1 calc R . . C5 C 0.8198(4) 0.7613(3) 0.05737(10) 0.0471(6) Uani 1 1 d . . . H5 H 0.9205 0.6731 0.0486 0.056 Uiso 1 1 calc R . . C6 C 0.6213(4) 0.7272(3) 0.08729(9) 0.0423(6) Uani 1 1 d . . . C7 C 0.2331(5) 0.4421(3) 0.13957(11) 0.0516(6) Uani 1 1 d . . . H7 H 0.1897 0.4093 0.1025 0.062 Uiso 1 1 calc R . . N1 N 0.7654(6) 1.2295(3) 0.03363(12) 0.0647(7) Uani 1 1 d . . . C9 C 0.4726(4) 0.8576(3) 0.09968(10) 0.0471(6) Uani 1 1 d . . . H9 H 0.3377 0.8347 0.1194 0.057 Uiso 1 1 calc R . . C10 C 0.5010(5) 0.5736(3) 0.20307(10) 0.0504(6) Uani 1 1 d . . . H10 H 0.6392 0.6293 0.2090 0.060 Uiso 1 1 calc R . . C11 C 0.0947(5) 0.4066(3) 0.18633(11) 0.0525(7) Uani 1 1 d . . . H11 H -0.0425 0.3496 0.1803 0.063 Uiso 1 1 calc R . . C12 C 0.3598(5) 0.5377(4) 0.24912(10) 0.0514(7) Uani 1 1 d . . . H12 H 0.4037 0.5710 0.2861 0.062 Uiso 1 1 calc R . . C13 C 0.1546(4) 0.4533(3) 0.24174(11) 0.0470(6) Uani 1 1 d . . . C8 C 0.0015(5) 0.4191(4) 0.29252(12) 0.0634(8) Uani 1 1 d . . . H8A H -0.1460 0.4684 0.2855 0.095 Uiso 1 1 calc R . . H8B H 0.0665 0.4692 0.3266 0.095 Uiso 1 1 calc R . . H8C H -0.0139 0.2979 0.2979 0.095 Uiso 1 1 calc R . . H1A H 0.719(7) 1.317(5) 0.0593(14) 0.094(12) Uiso 1 1 d . . . H1B H 0.903(7) 1.247(5) 0.0235(13) 0.072(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0731(12) 0.0436(10) 0.0536(10) -0.0006(8) 0.0196(10) 0.0036(10) C1 0.0536(14) 0.0444(13) 0.0370(12) -0.0006(11) -0.0003(11) -0.0001(12) C2 0.0448(13) 0.0549(15) 0.0438(13) -0.0004(12) 0.0089(11) 0.0004(12) C3 0.0521(14) 0.0356(12) 0.0457(13) 0.0022(10) 0.0057(11) 0.0047(11) C4 0.0540(15) 0.0500(16) 0.0469(13) 0.0031(11) 0.0088(12) 0.0162(13) C5 0.0492(14) 0.0473(15) 0.0447(13) -0.0055(11) 0.0062(11) 0.0087(12) C6 0.0489(13) 0.0445(14) 0.0335(12) -0.0008(10) 0.0011(10) 0.0015(12) C7 0.0582(15) 0.0475(14) 0.0492(14) -0.0050(12) -0.0079(12) 0.0014(14) N1 0.0757(19) 0.0479(14) 0.0706(17) 0.0058(12) 0.0174(15) -0.0016(14) C9 0.0422(12) 0.0543(15) 0.0449(13) 0.0036(11) 0.0093(12) 0.0060(12) C10 0.0447(13) 0.0532(15) 0.0533(14) 0.0034(12) -0.0012(12) -0.0083(13) C11 0.0438(13) 0.0479(15) 0.0658(16) 0.0001(12) -0.0008(13) -0.0044(12) C12 0.0540(14) 0.0590(17) 0.0412(13) 0.0069(12) -0.0037(11) -0.0009(14) C13 0.0466(13) 0.0401(13) 0.0542(14) 0.0095(12) 0.0022(12) 0.0055(11) C8 0.0593(17) 0.0661(18) 0.0648(16) 0.0155(15) 0.0136(14) 0.0032(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C6 1.391(3) . ? O1 C3 1.397(3) . ? C1 C2 1.384(4) . ? C1 C4 1.384(4) . ? C1 N1 1.418(4) . ? C2 C5 1.381(4) . ? C2 H2 0.9300 . ? C3 C10 1.372(4) . ? C3 C7 1.373(4) . ? C4 C9 1.383(4) . ? C4 H4 0.9300 . ? C5 C6 1.379(3) . ? C5 H5 0.9300 . ? C6 C9 1.372(3) . ? C7 C11 1.380(4) . ? C7 H7 0.9300 . ? N1 H1A 0.95(4) . ? N1 H1B 0.85(4) . ? C9 H9 0.9300 . ? C10 C12 1.377(4) . ? C10 H10 0.9300 . ? C11 C13 1.378(4) . ? C11 H11 0.9300 . ? C12 C13 1.382(4) . ? C12 H12 0.9300 . ? C13 C8 1.502(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 C3 116.70(18) . . ? C2 C1 C4 117.9(2) . . ? C2 C1 N1 121.6(2) . . ? C4 C1 N1 120.4(3) . . ? C5 C2 C1 121.3(2) . . ? C5 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C10 C3 C7 120.4(2) . . ? C10 C3 O1 120.6(2) . . ? C7 C3 O1 118.9(2) . . ? C9 C4 C1 121.2(2) . . ? C9 C4 H4 119.4 . . ? C1 C4 H4 119.4 . . ? C6 C5 C2 119.8(2) . . ? C6 C5 H5 120.1 . . ? C2 C5 H5 120.1 . . ? C9 C6 C5 119.8(2) . . ? C9 C6 O1 123.3(2) . . ? C5 C6 O1 116.9(2) . . ? C3 C7 C11 119.3(2) . . ? C3 C7 H7 120.4 . . ? C11 C7 H7 120.4 . . ? C1 N1 H1A 115(2) . . ? C1 N1 H1B 114(2) . . ? H1A N1 H1B 110(3) . . ? C6 C9 C4 120.1(2) . . ? C6 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? C3 C10 C12 119.4(2) . . ? C3 C10 H10 120.3 . . ? C12 C10 H10 120.3 . . ? C13 C11 C7 121.7(2) . . ? C13 C11 H11 119.1 . . ? C7 C11 H11 119.1 . . ? C10 C12 C13 121.6(2) . . ? C10 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C11 C13 C12 117.6(2) . . ? C11 C13 C8 121.9(2) . . ? C12 C13 C8 120.5(2) . . ? C13 C8 H8A 109.5 . . ? C13 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C13 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.152 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.030 # END# data_16 _database_code_depnum_ccdc_archive 'CCDC 265011' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4'-Cyano-4-nitrodiphenylether ; _chemical_name_common 4'-Cyano-4-nitrodiphenylether _chemical_melting_point 433 _chemical_formula_moiety 'C13 H8 N2 O3' _chemical_formula_sum 'C13 H8 N2 O3' _chemical_formula_weight 240.21 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.374(3) _cell_length_b 7.2793(16) _cell_length_c 11.782(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.415(2) _cell_angle_gamma 90.00 _cell_volume 1110.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2114 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 25.90 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496.0 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5947 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1955 _reflns_number_gt 1361 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+0.3117P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1955 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1623 _refine_ls_wR_factor_gt 0.1479 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.84586(14) 0.0670(3) 0.98464(15) 0.0653(6) Uani 1 1 d . . . C11 C 0.5856(2) 0.1570(4) 1.1006(2) 0.0492(7) Uani 1 1 d . . . C8 C 0.7558(2) 0.0966(4) 1.0183(2) 0.0493(7) Uani 1 1 d . . . C13 C 0.7516(2) 0.0265(4) 1.1261(2) 0.0543(7) Uani 1 1 d . . . H13 H 0.8070 -0.0396 1.1710 0.065 Uiso 1 1 calc R . . C5 C 0.8447(2) 0.0474(4) 0.8676(2) 0.0520(7) Uani 1 1 d . . . C3 C 0.9369(2) 0.0848(4) 0.7208(2) 0.0605(8) Uani 1 1 d . . . H3 H 0.9948 0.1261 0.6981 0.073 Uiso 1 1 calc R . . C7 C 0.7716(2) -0.0611(4) 0.6745(2) 0.0549(7) Uani 1 1 d . . . H7 H 0.7175 -0.1163 0.6200 0.066 Uiso 1 1 calc R . . C1 C 0.8629(2) -0.0286(4) 0.5209(3) 0.0601(8) Uani 1 1 d . . . C2 C 0.8576(2) -0.0007(4) 0.6405(2) 0.0508(7) Uani 1 1 d . . . C9 C 0.6751(2) 0.1995(4) 0.9533(2) 0.0558(8) Uani 1 1 d . . . H9 H 0.6788 0.2479 0.8814 0.067 Uiso 1 1 calc R . . C6 C 0.7655(2) -0.0399(4) 0.7887(2) 0.0574(8) Uani 1 1 d . . . H6 H 0.7086 -0.0841 0.8123 0.069 Uiso 1 1 calc R . . C10 C 0.5894(2) 0.2304(4) 0.9945(2) 0.0536(7) Uani 1 1 d . . . H10 H 0.5348 0.3000 0.9513 0.064 Uiso 1 1 calc R . . O2 O 0.42095(19) 0.2772(4) 1.0830(2) 0.0939(8) Uani 1 1 d . . . C4 C 0.9300(2) 0.1087(4) 0.8346(2) 0.0584(8) Uani 1 1 d . . . H4 H 0.9832 0.1663 0.8889 0.070 Uiso 1 1 calc R . . O3 O 0.48842(18) 0.1240(4) 1.2371(2) 0.0947(9) Uani 1 1 d . . . C12 C 0.6654(2) 0.0550(4) 1.1663(2) 0.0548(8) Uani 1 1 d . . . H12 H 0.6610 0.0056 1.2377 0.066 Uiso 1 1 calc R . . N1 N 0.4935(2) 0.1885(4) 1.1437(2) 0.0658(7) Uani 1 1 d . . . N2 N 0.8646(2) -0.0530(4) 0.4264(2) 0.0799(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0508(11) 0.0959(17) 0.0465(11) 0.0051(10) 0.0068(9) 0.0033(11) C11 0.0518(16) 0.0527(17) 0.0422(14) -0.0110(13) 0.0102(12) -0.0110(14) C8 0.0503(16) 0.0529(18) 0.0425(15) -0.0012(12) 0.0074(13) -0.0069(14) C13 0.0607(18) 0.0519(18) 0.0451(15) 0.0015(13) 0.0033(13) 0.0016(14) C5 0.0477(16) 0.0593(19) 0.0473(15) 0.0045(13) 0.0086(13) 0.0073(14) C3 0.0488(17) 0.074(2) 0.0599(18) 0.0000(15) 0.0161(14) -0.0015(15) C7 0.0556(17) 0.0521(18) 0.0539(17) -0.0015(13) 0.0077(14) -0.0021(14) C1 0.0583(18) 0.064(2) 0.0570(18) 0.0002(15) 0.0133(15) 0.0073(15) C2 0.0539(17) 0.0480(17) 0.0488(16) 0.0025(13) 0.0097(13) 0.0102(14) C9 0.0580(17) 0.0637(19) 0.0428(15) 0.0103(13) 0.0073(13) -0.0033(15) C6 0.0517(17) 0.061(2) 0.0591(18) 0.0036(14) 0.0130(14) -0.0086(14) C10 0.0521(16) 0.0569(18) 0.0475(16) 0.0002(13) 0.0044(13) -0.0017(14) O2 0.0705(15) 0.118(2) 0.0935(18) -0.0007(15) 0.0205(14) 0.0127(15) C4 0.0419(15) 0.072(2) 0.0580(17) -0.0042(15) 0.0054(13) 0.0007(15) O3 0.0838(17) 0.149(2) 0.0553(13) -0.0077(15) 0.0245(12) -0.0206(16) C12 0.0711(19) 0.0546(18) 0.0382(14) -0.0026(13) 0.0128(14) -0.0082(15) N1 0.0650(17) 0.0790(19) 0.0509(15) -0.0127(14) 0.0098(13) -0.0123(15) N2 0.081(2) 0.102(2) 0.0598(17) -0.0095(16) 0.0239(15) 0.0011(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.376(3) . ? O1 C5 1.383(3) . ? C11 C12 1.371(4) . ? C11 C10 1.372(4) . ? C11 N1 1.463(4) . ? C8 C9 1.379(4) . ? C8 C13 1.383(4) . ? C13 C12 1.366(4) . ? C13 H13 0.9300 . ? C5 C4 1.368(4) . ? C5 C6 1.379(4) . ? C3 C4 1.378(4) . ? C3 C2 1.381(4) . ? C3 H3 0.9300 . ? C7 C6 1.377(4) . ? C7 C2 1.381(4) . ? C7 H7 0.9300 . ? C1 N2 1.133(3) . ? C1 C2 1.443(4) . ? C9 C10 1.369(4) . ? C9 H9 0.9300 . ? C6 H6 0.9300 . ? C10 H10 0.9300 . ? O2 N1 1.234(3) . ? C4 H4 0.9300 . ? O3 N1 1.214(3) . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 C5 120.7(2) . . ? C12 C11 C10 121.7(3) . . ? C12 C11 N1 119.6(2) . . ? C10 C11 N1 118.7(3) . . ? O1 C8 C9 123.1(2) . . ? O1 C8 C13 116.5(2) . . ? C9 C8 C13 120.4(3) . . ? C12 C13 C8 119.5(3) . . ? C12 C13 H13 120.2 . . ? C8 C13 H13 120.2 . . ? C4 C5 C6 121.0(3) . . ? C4 C5 O1 116.5(2) . . ? C6 C5 O1 122.4(3) . . ? C4 C3 C2 119.8(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C6 C7 C2 120.3(3) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? N2 C1 C2 178.1(3) . . ? C7 C2 C3 119.9(2) . . ? C7 C2 C1 119.1(3) . . ? C3 C2 C1 121.1(3) . . ? C10 C9 C8 120.0(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C7 C6 C5 119.2(3) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C9 C10 C11 118.9(3) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C13 C12 C11 119.5(3) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? O3 N1 O2 121.0(3) . . ? O3 N1 C11 119.7(3) . . ? O2 N1 C11 119.3(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.180 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.039 # END# data_17 _database_code_depnum_ccdc_archive 'CCDC 265012' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-Dicyanodiphenyl ether ; _chemical_name_common "4,4'-Dicyanodiphenyl ether" _chemical_melting_point 258 _chemical_formula_moiety 'C14 H8 N2 O' _chemical_formula_sum 'C14 H8 N2 O' _chemical_formula_weight 220.22 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5909(18) _cell_length_b 7.4306(11) _cell_length_c 11.8337(17) _cell_angle_alpha 90.00 _cell_angle_beta 96.601(2) _cell_angle_gamma 90.00 _cell_volume 1099.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3344 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 25.98 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8953 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1940 _reflns_number_gt 1467 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.2144P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1940 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.84452(9) 0.06317(19) -0.04354(9) 0.0623(4) Uani 1 1 d . . . C5 C 0.75262(13) 0.0847(2) -0.11735(13) 0.0461(4) Uani 1 1 d . . . C8 C 0.84173(13) 0.0446(2) 0.07226(13) 0.0483(4) Uani 1 1 d . . . C4 C 0.75962(14) 0.0326(2) -0.22763(13) 0.0482(4) Uani 1 1 d . . . H4 H 0.8222 -0.0194 -0.2471 0.058 Uiso 1 1 calc R . . C14 C 0.86034(14) -0.0222(3) 0.42450(16) 0.0544(5) Uani 1 1 d . . . C9 C 0.92595(14) 0.1195(3) 0.14027(14) 0.0529(5) Uani 1 1 d . . . H9 H 0.9781 0.1840 0.1080 0.064 Uiso 1 1 calc R . . C2 C 0.58141(13) 0.1360(2) -0.28021(13) 0.0464(4) Uani 1 1 d . . . C7 C 0.57551(15) 0.1889(2) -0.16874(15) 0.0533(5) Uani 1 1 d . . . H7 H 0.5133 0.2418 -0.1490 0.064 Uiso 1 1 calc R . . C3 C 0.67433(14) 0.0573(2) -0.30882(14) 0.0496(5) Uani 1 1 d . . . H3 H 0.6788 0.0212 -0.3834 0.059 Uiso 1 1 calc R . . C12 C 0.77067(15) -0.0724(2) 0.23388(15) 0.0547(5) Uani 1 1 d . . . H12 H 0.7179 -0.1361 0.2657 0.066 Uiso 1 1 calc R . . C10 C 0.93273(14) 0.0988(3) 0.25605(14) 0.0533(5) Uani 1 1 d . . . H10 H 0.9895 0.1493 0.3026 0.064 Uiso 1 1 calc R . . C11 C 0.85459(14) 0.0024(2) 0.30351(13) 0.0464(4) Uani 1 1 d . . . C1 C 0.49329(15) 0.1654(3) -0.36609(15) 0.0549(5) Uani 1 1 d . . . C6 C 0.66087(15) 0.1637(3) -0.08771(14) 0.0550(5) Uani 1 1 d . . . H6 H 0.6569 0.1998 -0.0131 0.066 Uiso 1 1 calc R . . N2 N 0.86393(13) -0.0442(3) 0.52001(14) 0.0735(5) Uani 1 1 d . . . C13 C 0.76454(15) -0.0536(3) 0.11780(15) 0.0571(5) Uani 1 1 d . . . H13 H 0.7089 -0.1065 0.0707 0.068 Uiso 1 1 calc R . . N1 N 0.42451(15) 0.1888(3) -0.43587(14) 0.0769(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0481(8) 0.1000(11) 0.0383(7) -0.0027(6) 0.0026(6) 0.0015(7) C5 0.0440(10) 0.0527(10) 0.0411(10) 0.0009(7) 0.0028(8) -0.0037(8) C8 0.0447(10) 0.0607(11) 0.0392(10) -0.0025(8) 0.0032(8) 0.0067(9) C4 0.0459(10) 0.0580(11) 0.0417(10) -0.0004(8) 0.0092(8) 0.0035(8) C14 0.0502(11) 0.0652(12) 0.0476(11) 0.0001(9) 0.0048(8) 0.0058(9) C9 0.0404(10) 0.0693(12) 0.0489(10) 0.0060(9) 0.0044(8) -0.0018(9) C2 0.0489(10) 0.0477(10) 0.0423(9) 0.0040(8) 0.0044(8) -0.0010(8) C7 0.0499(11) 0.0584(11) 0.0525(11) -0.0035(8) 0.0092(9) 0.0077(9) C3 0.0556(11) 0.0571(11) 0.0363(9) -0.0019(8) 0.0065(8) 0.0002(9) C12 0.0555(12) 0.0573(11) 0.0522(11) 0.0017(8) 0.0096(9) -0.0066(9) C10 0.0432(10) 0.0688(12) 0.0461(10) -0.0022(9) -0.0032(8) -0.0012(9) C11 0.0473(10) 0.0491(10) 0.0426(10) 0.0013(8) 0.0039(8) 0.0101(8) C1 0.0545(12) 0.0624(12) 0.0475(11) 0.0062(9) 0.0052(9) 0.0040(9) C6 0.0567(12) 0.0670(12) 0.0416(10) -0.0105(9) 0.0076(9) 0.0036(10) N2 0.0684(12) 0.1032(14) 0.0486(10) 0.0060(9) 0.0061(8) 0.0002(10) C13 0.0557(11) 0.0652(12) 0.0486(11) -0.0077(9) -0.0008(9) -0.0119(9) N1 0.0658(12) 0.1011(14) 0.0611(11) 0.0093(10) -0.0036(9) 0.0126(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.377(2) . ? O1 C8 1.3817(19) . ? C5 C4 1.374(2) . ? C5 C6 1.377(2) . ? C8 C9 1.373(2) . ? C8 C13 1.374(2) . ? C4 C3 1.369(2) . ? C4 H4 0.9300 . ? C14 N2 1.138(2) . ? C14 C11 1.437(2) . ? C9 C10 1.372(2) . ? C9 H9 0.9300 . ? C2 C3 1.384(2) . ? C2 C7 1.387(2) . ? C2 C1 1.433(2) . ? C7 C6 1.369(2) . ? C7 H7 0.9300 . ? C3 H3 0.9300 . ? C12 C13 1.374(2) . ? C12 C11 1.380(2) . ? C12 H12 0.9300 . ? C10 C11 1.387(2) . ? C10 H10 0.9300 . ? C1 N1 1.139(2) . ? C6 H6 0.9300 . ? C13 H13 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 O1 C8 121.71(13) . . ? C4 C5 O1 115.41(15) . . ? C4 C5 C6 120.63(16) . . ? O1 C5 C6 123.82(15) . . ? C9 C8 C13 121.25(16) . . ? C9 C8 O1 115.77(15) . . ? C13 C8 O1 122.81(15) . . ? C3 C4 C5 119.88(16) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N2 C14 C11 178.8(2) . . ? C10 C9 C8 119.68(16) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C3 C2 C7 119.45(15) . . ? C3 C2 C1 119.89(15) . . ? C7 C2 C1 120.64(16) . . ? C6 C7 C2 120.27(16) . . ? C6 C7 H7 119.9 . . ? C2 C7 H7 119.9 . . ? C4 C3 C2 120.14(15) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C13 C12 C11 120.46(17) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C9 C10 C11 119.79(16) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 119.77(15) . . ? C12 C11 C14 119.42(16) . . ? C10 C11 C14 120.81(16) . . ? N1 C1 C2 178.73(19) . . ? C7 C6 C5 119.62(16) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C13 C12 119.04(17) . . ? C8 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.157 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.033 # END# data_18 _database_code_depnum_ccdc_archive 'CCDC 265013' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-Methylphenoxy)benzonitrile ; _chemical_name_common 4-(4-Methylphenoxy)benzonitrile _chemical_melting_point 343 _chemical_formula_moiety 'C14 H11 N O' _chemical_formula_sum 'C14 H11 N O' _chemical_formula_weight 209.24 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5167(19) _cell_length_b 6.7036(10) _cell_length_c 13.680(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.477(2) _cell_angle_gamma 90.00 _cell_volume 1146.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2202 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 25.96 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4119 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2005 _reflns_number_gt 1585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+0.1176P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2005 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C14 C 0.46469(12) 0.3272(3) 0.65257(11) 0.0571(4) Uani 1 1 d . . . H14 H 0.4857 0.1973 0.6676 0.069 Uiso 1 1 calc R . . O1 O 0.28838(9) 0.22593(18) 0.66890(10) 0.0739(4) Uani 1 1 d . . . C12 C 0.54006(12) 0.4694(3) 0.63405(11) 0.0584(5) Uani 1 1 d . . . H12 H 0.6122 0.4357 0.6367 0.070 Uiso 1 1 calc R . . C10 C 0.40156(13) 0.7123(3) 0.60739(12) 0.0603(4) Uani 1 1 d . . . H10 H 0.3805 0.8420 0.5919 0.072 Uiso 1 1 calc R . . C13 C 0.58875(13) 0.8111(3) 0.59273(12) 0.0635(5) Uani 1 1 d . . . C11 C 0.50920(12) 0.6627(3) 0.61139(11) 0.0543(4) Uani 1 1 d . . . C8 C 0.35747(12) 0.3776(3) 0.64882(11) 0.0551(4) Uani 1 1 d . . . N1 N 0.65267(13) 0.9275(3) 0.57872(13) 0.0836(5) Uani 1 1 d . . . C9 C 0.32581(13) 0.5701(3) 0.62626(13) 0.0620(5) Uani 1 1 d . . . H9 H 0.2536 0.6035 0.6238 0.074 Uiso 1 1 calc R . . C4 C 0.12441(14) 0.3365(3) 0.73533(14) 0.0645(5) Uani 1 1 d . . . H4 H 0.1609 0.3669 0.7941 0.077 Uiso 1 1 calc R . . C5 C 0.17833(13) 0.2640(3) 0.65813(14) 0.0614(5) Uani 1 1 d . . . C7 C 0.01595(15) 0.2497(3) 0.56276(15) 0.0780(6) Uani 1 1 d . . . H7 H -0.0202 0.2208 0.5036 0.094 Uiso 1 1 calc R . . C2 C -0.04067(14) 0.3218(3) 0.63903(15) 0.0665(5) Uani 1 1 d . . . C3 C 0.01520(14) 0.3642(3) 0.72500(14) 0.0676(5) Uani 1 1 d . . . H3 H -0.0214 0.4128 0.7777 0.081 Uiso 1 1 calc R . . C6 C 0.12541(15) 0.2189(3) 0.57151(14) 0.0743(5) Uani 1 1 d . . . H6 H 0.1622 0.1683 0.5193 0.089 Uiso 1 1 calc R . . C1 C -0.16063(15) 0.3525(4) 0.62940(19) 0.0930(7) Uani 1 1 d . . . H1A H -0.1892 0.3585 0.6933 0.139 Uiso 1 1 calc R . . H1B H -0.1928 0.2434 0.5935 0.139 Uiso 1 1 calc R . . H1C H -0.1758 0.4751 0.5953 0.139 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C14 0.0516(9) 0.0593(10) 0.0602(9) 0.0011(8) 0.0006(7) 0.0076(8) O1 0.0499(7) 0.0589(8) 0.1131(10) 0.0145(7) 0.0049(6) -0.0009(6) C12 0.0426(8) 0.0756(12) 0.0570(9) -0.0037(8) 0.0008(7) 0.0050(8) C10 0.0546(9) 0.0567(10) 0.0691(10) 0.0049(8) -0.0041(8) 0.0000(8) C13 0.0530(10) 0.0742(12) 0.0632(10) -0.0021(9) 0.0011(8) -0.0078(9) C11 0.0478(9) 0.0656(11) 0.0493(8) -0.0032(7) -0.0006(7) -0.0053(8) C8 0.0481(9) 0.0570(10) 0.0600(9) 0.0016(7) 0.0015(7) -0.0016(8) N1 0.0663(10) 0.0889(13) 0.0956(12) 0.0034(10) 0.0036(9) -0.0203(9) C9 0.0435(8) 0.0634(11) 0.0785(11) 0.0075(9) -0.0025(8) 0.0022(8) C4 0.0579(10) 0.0551(10) 0.0796(12) -0.0057(9) -0.0056(9) -0.0037(8) C5 0.0482(9) 0.0516(10) 0.0845(12) 0.0051(9) 0.0027(8) -0.0049(8) C7 0.0708(12) 0.0810(14) 0.0806(13) -0.0029(10) -0.0146(10) -0.0077(11) C2 0.0516(10) 0.0519(10) 0.0953(13) 0.0033(9) -0.0039(9) -0.0068(8) C3 0.0580(10) 0.0575(11) 0.0876(13) -0.0061(9) 0.0053(9) 0.0000(9) C6 0.0715(12) 0.0766(13) 0.0754(12) -0.0027(10) 0.0096(10) -0.0031(10) C1 0.0554(11) 0.0831(15) 0.139(2) 0.0046(13) -0.0125(12) -0.0039(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C14 C12 1.372(2) . ? C14 C8 1.383(2) . ? C14 H14 0.9300 . ? O1 C8 1.3702(19) . ? O1 C5 1.402(2) . ? C12 C11 1.384(3) . ? C12 H12 0.9300 . ? C10 C9 1.377(2) . ? C10 C11 1.387(2) . ? C10 H10 0.9300 . ? C13 N1 1.140(2) . ? C13 C11 1.438(2) . ? C8 C9 1.381(2) . ? C9 H9 0.9300 . ? C4 C5 1.367(3) . ? C4 C3 1.381(2) . ? C4 H4 0.9300 . ? C5 C6 1.366(3) . ? C7 C2 1.374(3) . ? C7 C6 1.386(3) . ? C7 H7 0.9300 . ? C2 C3 1.372(3) . ? C2 C1 1.516(2) . ? C3 H3 0.9300 . ? C6 H6 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 C14 C8 119.82(16) . . ? C12 C14 H14 120.1 . . ? C8 C14 H14 120.1 . . ? C8 O1 C5 117.99(13) . . ? C14 C12 C11 120.29(15) . . ? C14 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C9 C10 C11 120.15(16) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? N1 C13 C11 179.1(2) . . ? C12 C11 C10 119.66(15) . . ? C12 C11 C13 119.92(15) . . ? C10 C11 C13 120.41(16) . . ? O1 C8 C9 124.11(14) . . ? O1 C8 C14 115.55(15) . . ? C9 C8 C14 120.34(16) . . ? C10 C9 C8 119.72(15) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C5 C4 C3 119.23(17) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 120.78(16) . . ? C6 C5 O1 119.21(17) . . ? C4 C5 O1 119.94(16) . . ? C2 C7 C6 121.82(18) . . ? C2 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C3 C2 C7 117.60(17) . . ? C3 C2 C1 120.84(19) . . ? C7 C2 C1 121.55(18) . . ? C2 C3 C4 121.71(18) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C6 C7 118.84(18) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.159 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.061 # END# data_19 _database_code_depnum_ccdc_archive 'CCDC 265014' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-Methoxyphenoxy)benzonitrile ; _chemical_name_common 4-(4-Methoxyphenoxy)benzonitrile _chemical_melting_point 381 _chemical_formula_moiety 'C14 H11 N O2' _chemical_formula_sum 'C14 H11 N O2' _chemical_formula_weight 225.24 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.319(2) _cell_length_b 7.9156(14) _cell_length_c 12.276(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.166(2) _cell_angle_gamma 90.00 _cell_volume 1149.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2958 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 26.08 _exptl_crystal_description Irregular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5018 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 26.08 _reflns_number_total 2268 _reflns_number_gt 1815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.1146P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2268 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1133 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.60447(8) 0.09300(13) 0.46546(8) 0.0617(3) Uani 1 1 d . . . O2 O 0.67349(9) -0.03690(14) 0.04816(8) 0.0702(3) Uani 1 1 d . . . C10 C 0.62742(11) 0.05558(17) 0.36573(11) 0.0506(3) Uani 1 1 d . . . C5 C 0.75840(11) 0.04151(17) 0.01506(11) 0.0526(3) Uani 1 1 d . . . C9 C 0.70909(12) -0.05777(19) 0.35497(12) 0.0573(4) Uani 1 1 d . . . H9 H 0.7527 -0.1147 0.4183 0.069 Uiso 1 1 calc R . . C2 C 0.92173(11) 0.18992(17) -0.06771(11) 0.0521(3) Uani 1 1 d . . . C4 C 0.83856(12) 0.14474(19) 0.08450(11) 0.0586(4) Uani 1 1 d . . . H4 H 0.8378 0.1641 0.1590 0.070 Uiso 1 1 calc R . . C6 C 0.66145(12) -0.00216(19) 0.15646(12) 0.0577(4) Uani 1 1 d . . . C3 C 0.91965(12) 0.21891(19) 0.04270(11) 0.0592(4) Uani 1 1 d . . . H3 H 0.9736 0.2892 0.0891 0.071 Uiso 1 1 calc R . . C11 C 0.56277(12) 0.1392(2) 0.27048(12) 0.0599(4) Uani 1 1 d . . . H11 H 0.5076 0.2155 0.2774 0.072 Uiso 1 1 calc R . . C8 C 0.72579(13) -0.0863(2) 0.24922(12) 0.0624(4) Uani 1 1 d . . . H8 H 0.7806 -0.1626 0.2415 0.075 Uiso 1 1 calc R . . C12 C 1.00456(12) 0.2703(2) -0.11248(12) 0.0627(4) Uani 1 1 d . . . C1 C 0.84210(12) 0.08322(19) -0.13591(11) 0.0591(4) Uani 1 1 d . . . H1 H 0.8441 0.0606 -0.2097 0.071 Uiso 1 1 calc R . . C7 C 0.57947(12) 0.1105(2) 0.16599(12) 0.0616(4) Uani 1 1 d . . . H7 H 0.5358 0.1666 0.1023 0.074 Uiso 1 1 calc R . . C13 C 0.65702(13) -0.0083(2) 0.56134(12) 0.0662(4) Uani 1 1 d . . . H13A H 0.6378 -0.1247 0.5443 0.099 Uiso 1 1 calc R . . H13B H 0.6312 0.0264 0.6248 0.099 Uiso 1 1 calc R . . H13C H 0.7375 0.0051 0.5796 0.099 Uiso 1 1 calc R . . N1 N 1.06850(12) 0.3356(2) -0.15015(12) 0.0869(5) Uani 1 1 d . . . C14 C 0.76036(13) 0.01088(18) -0.09465(11) 0.0593(4) Uani 1 1 d . . . H14 H 0.7061 -0.0591 -0.1410 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0632(6) 0.0703(7) 0.0545(6) 0.0038(5) 0.0212(5) 0.0072(5) O2 0.0783(7) 0.0832(7) 0.0516(6) -0.0120(5) 0.0220(5) -0.0308(6) C10 0.0478(7) 0.0518(8) 0.0525(7) 0.0004(6) 0.0141(6) -0.0066(6) C5 0.0574(8) 0.0516(8) 0.0476(7) -0.0007(6) 0.0125(6) -0.0039(6) C9 0.0567(8) 0.0610(8) 0.0526(8) 0.0037(6) 0.0126(6) 0.0054(6) C2 0.0506(7) 0.0548(8) 0.0501(7) 0.0044(6) 0.0129(6) 0.0046(6) C4 0.0641(8) 0.0668(9) 0.0455(7) -0.0102(6) 0.0160(6) -0.0086(7) C6 0.0599(8) 0.0647(9) 0.0493(8) -0.0038(6) 0.0165(6) -0.0170(7) C3 0.0568(8) 0.0647(9) 0.0532(8) -0.0091(7) 0.0105(6) -0.0091(7) C11 0.0537(7) 0.0608(9) 0.0654(9) 0.0089(7) 0.0169(7) 0.0037(6) C8 0.0611(8) 0.0664(9) 0.0608(9) -0.0039(7) 0.0191(7) 0.0035(7) C12 0.0576(8) 0.0728(10) 0.0557(8) 0.0032(7) 0.0126(7) -0.0010(7) C1 0.0697(9) 0.0643(9) 0.0430(7) -0.0031(6) 0.0154(6) -0.0009(7) C7 0.0585(8) 0.0660(9) 0.0559(8) 0.0123(7) 0.0087(6) -0.0063(7) C13 0.0671(9) 0.0799(11) 0.0510(8) 0.0033(7) 0.0153(7) 0.0047(8) N1 0.0733(9) 0.1124(12) 0.0778(9) 0.0072(9) 0.0254(8) -0.0176(9) C14 0.0691(9) 0.0596(8) 0.0453(7) -0.0065(6) 0.0095(6) -0.0121(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C10 1.3636(16) . ? O1 C13 1.4223(17) . ? O2 C5 1.3714(16) . ? O2 C6 1.4053(17) . ? C10 C9 1.381(2) . ? C10 C11 1.3862(19) . ? C5 C14 1.3753(19) . ? C5 C4 1.3787(19) . ? C9 C8 1.3884(19) . ? C9 H9 0.9300 . ? C2 C3 1.3819(18) . ? C2 C1 1.3853(19) . ? C2 C12 1.4355(19) . ? C4 C3 1.3752(19) . ? C4 H4 0.9300 . ? C6 C8 1.366(2) . ? C6 C7 1.376(2) . ? C3 H3 0.9300 . ? C11 C7 1.373(2) . ? C11 H11 0.9300 . ? C8 H8 0.9300 . ? C12 N1 1.1418(19) . ? C1 C14 1.372(2) . ? C1 H1 0.9300 . ? C7 H7 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 O1 C13 117.40(11) . . ? C5 O2 C6 118.80(10) . . ? O1 C10 C9 124.44(12) . . ? O1 C10 C11 116.07(12) . . ? C9 C10 C11 119.48(13) . . ? O2 C5 C14 115.67(12) . . ? O2 C5 C4 123.99(12) . . ? C14 C5 C4 120.34(13) . . ? C10 C9 C8 119.79(13) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C3 C2 C1 119.38(12) . . ? C3 C2 C12 120.75(13) . . ? C1 C2 C12 119.87(12) . . ? C3 C4 C5 119.47(12) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C8 C6 C7 120.95(13) . . ? C8 C6 O2 120.23(14) . . ? C7 C6 O2 118.71(13) . . ? C4 C3 C2 120.59(13) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C7 C11 C10 120.56(14) . . ? C7 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C6 C8 C9 119.82(14) . . ? C6 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? N1 C12 C2 178.43(16) . . ? C14 C1 C2 120.02(12) . . ? C14 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C11 C7 C6 119.41(13) . . ? C11 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 C14 C5 120.18(13) . . ? C1 C14 H14 119.9 . . ? C5 C14 H14 119.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.124 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.048 # END# data_20 _database_code_depnum_ccdc_archive 'CCDC 265015' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Nitrodiphenyl ether ; _chemical_name_common '4-Nitrodiphenyl ether' _chemical_melting_point 329 _chemical_formula_moiety 'C12 H9 N O3' _chemical_formula_sum 'C12 H9 N O3' _chemical_formula_weight 215.20 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7833(14) _cell_length_b 8.9802(18) _cell_length_c 17.306(4) _cell_angle_alpha 87.76(3) _cell_angle_beta 88.25(3) _cell_angle_gamma 88.88(3) _cell_volume 1052.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.02 _cell_measurement_theta_max 10.94 _exptl_crystal_description Blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius Mach3 four-circle' _diffrn_measurement_method 'Profile data from omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% none _diffrn_reflns_number 3691 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0790 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3691 _reflns_number_gt 1371 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'WinGX (Farrugia, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3691 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1818 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O5 O 0.0450(3) 0.3573(2) 0.21570(14) 0.0833(8) Uani 1 1 d . . . C2 C -0.0122(5) 0.4588(4) 0.15929(19) 0.0616(9) Uani 1 1 d . . . C3 C -0.1526(6) 0.6501(4) 0.04671(18) 0.0649(9) Uani 1 1 d . . . C4 C 0.0259(5) 0.6768(4) 0.07768(19) 0.0744(11) Uani 1 1 d . . . H4 H 0.0986 0.7592 0.0607 0.089 Uiso 1 1 calc R . . C5 C 0.2033(6) 0.3906(4) 0.2620(2) 0.0663(10) Uani 1 1 d . . . C6 C -0.1899(5) 0.4327(4) 0.1268(2) 0.0717(10) Uani 1 1 d . . . H6 H -0.2614 0.3492 0.1429 0.086 Uiso 1 1 calc R . . C7 C 0.0961(5) 0.5799(4) 0.13428(19) 0.0710(10) Uani 1 1 d . . . H7 H 0.2174 0.5965 0.1557 0.085 Uiso 1 1 calc R . . O4 O -0.3934(5) 0.7289(3) -0.03756(17) 0.1277(12) Uani 1 1 d . . . O3 O -0.1311(5) 0.8574(4) -0.03547(16) 0.1161(11) Uani 1 1 d . . . N2 N -0.2311(6) 0.7522(4) -0.01335(19) 0.0886(10) Uani 1 1 d . . . C8 C -0.2622(5) 0.5297(4) 0.0709(2) 0.0774(11) Uani 1 1 d . . . H8 H -0.3839 0.5138 0.0496 0.093 Uiso 1 1 calc R . . C9 C 0.1746(5) 0.4880(4) 0.3199(2) 0.0754(11) Uani 1 1 d . . . H9 H 0.0535 0.5368 0.3267 0.090 Uiso 1 1 calc R . . C10 C 0.3783(6) 0.3184(4) 0.2511(2) 0.0832(11) Uani 1 1 d . . . H10 H 0.3963 0.2515 0.2116 0.100 Uiso 1 1 calc R . . C11 C 0.3269(7) 0.5135(4) 0.3682(2) 0.0856(12) Uani 1 1 d . . . H11 H 0.3086 0.5798 0.4079 0.103 Uiso 1 1 calc R . . C12 C 0.5020(7) 0.4428(5) 0.3583(3) 0.0919(13) Uani 1 1 d . . . H12 H 0.6041 0.4597 0.3914 0.110 Uiso 1 1 calc R . . C13 C 0.5298(6) 0.3465(5) 0.3000(3) 0.0957(13) Uani 1 1 d . . . H13 H 0.6519 0.2992 0.2929 0.115 Uiso 1 1 calc R . . O6 O 1.0235(3) 0.8692(2) 0.28246(14) 0.0836(8) Uani 1 1 d . . . C15 C 1.1576(6) 1.1522(4) 0.45184(19) 0.0677(10) Uani 1 1 d . . . C16 C 1.0590(5) 0.9674(4) 0.33853(19) 0.0630(9) Uani 1 1 d . . . C17 C 0.8539(6) 0.8884(4) 0.2399(2) 0.0653(9) Uani 1 1 d . . . C18 C 0.9200(5) 1.0657(4) 0.36742(19) 0.0674(10) Uani 1 1 d . . . H18 H 0.7931 1.0690 0.3484 0.081 Uiso 1 1 calc R . . O2 O 1.0885(5) 1.3383(3) 0.53695(18) 0.1209(12) Uani 1 1 d . . . C19 C 0.9702(6) 1.1595(4) 0.4249(2) 0.0728(10) Uani 1 1 d . . . H19 H 0.8777 1.2265 0.4449 0.087 Uiso 1 1 calc R . . O1 O 1.3782(5) 1.2390(3) 0.53735(16) 0.1217(12) Uani 1 1 d . . . C20 C 0.7028(7) 0.7948(4) 0.2548(2) 0.0823(11) Uani 1 1 d . . . H20 H 0.7099 0.7229 0.2948 0.099 Uiso 1 1 calc R . . N1 N 1.2109(6) 1.2506(4) 0.51341(19) 0.0885(11) Uani 1 1 d . . . C21 C 1.2956(5) 1.0541(5) 0.4237(2) 0.0816(11) Uani 1 1 d . . . H21 H 1.4224 1.0509 0.4427 0.098 Uiso 1 1 calc R . . C22 C 1.2459(5) 0.9605(4) 0.3672(2) 0.0818(11) Uani 1 1 d . . . H22 H 1.3384 0.8923 0.3482 0.098 Uiso 1 1 calc R . . C23 C 0.8463(6) 0.9937(4) 0.1806(2) 0.0808(11) Uani 1 1 d . . . H23 H 0.9520 1.0564 0.1701 0.097 Uiso 1 1 calc R . . C24 C 0.5272(7) 0.9122(6) 0.1516(3) 0.1053(16) Uani 1 1 d . . . H24 H 0.4153 0.9203 0.1219 0.126 Uiso 1 1 calc R . . C25 C 0.5396(7) 0.8066(6) 0.2106(3) 0.1057(15) Uani 1 1 d . . . H25 H 0.4356 0.7420 0.2206 0.127 Uiso 1 1 calc R . . C26 C 0.6816(8) 1.0055(5) 0.1371(2) 0.0959(14) Uani 1 1 d . . . H26 H 0.6747 1.0776 0.0972 0.115 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.095(2) 0.0650(16) 0.0900(19) 0.0114(14) -0.0250(16) -0.0107(14) C2 0.068(2) 0.056(2) 0.061(2) -0.0057(19) -0.008(2) -0.005(2) C3 0.080(3) 0.066(2) 0.049(2) -0.0036(19) -0.011(2) 0.005(2) C4 0.085(3) 0.073(3) 0.066(3) 0.000(2) -0.004(2) -0.018(2) C5 0.071(3) 0.066(3) 0.062(3) 0.007(2) -0.012(2) -0.004(2) C6 0.071(3) 0.077(3) 0.069(3) -0.004(2) -0.006(2) -0.022(2) C7 0.073(3) 0.072(3) 0.069(3) -0.001(2) -0.014(2) -0.015(2) O4 0.130(3) 0.131(3) 0.124(3) 0.0179(19) -0.067(2) -0.001(2) O3 0.151(3) 0.109(2) 0.087(2) 0.0291(18) -0.0180(19) -0.016(2) N2 0.109(3) 0.086(3) 0.072(2) -0.005(2) -0.016(2) 0.000(2) C8 0.073(3) 0.089(3) 0.072(3) -0.005(2) -0.015(2) -0.016(2) C9 0.075(3) 0.067(3) 0.084(3) -0.005(2) -0.003(2) 0.007(2) C10 0.092(3) 0.087(3) 0.069(3) 0.002(2) 0.006(2) 0.014(3) C11 0.111(4) 0.068(3) 0.078(3) -0.002(2) -0.011(3) -0.010(3) C12 0.097(4) 0.097(4) 0.081(3) 0.027(3) -0.022(3) -0.013(3) C13 0.074(3) 0.114(4) 0.097(3) 0.025(3) -0.007(3) 0.022(3) O6 0.0812(19) 0.0757(18) 0.096(2) -0.0270(15) -0.0193(15) 0.0157(14) C15 0.090(3) 0.061(3) 0.052(2) 0.0011(19) -0.007(2) -0.005(2) C16 0.067(3) 0.057(2) 0.064(2) -0.0028(19) 0.001(2) 0.004(2) C17 0.066(3) 0.059(2) 0.072(3) -0.016(2) -0.002(2) -0.001(2) C18 0.065(2) 0.066(2) 0.070(3) -0.003(2) -0.003(2) 0.010(2) O2 0.162(3) 0.107(3) 0.096(2) -0.0372(19) -0.009(2) 0.015(2) C19 0.091(3) 0.062(3) 0.064(2) -0.003(2) 0.001(2) 0.016(2) O1 0.137(3) 0.133(3) 0.099(2) -0.0231(18) -0.045(2) -0.010(2) C20 0.106(3) 0.079(3) 0.063(3) -0.009(2) 0.004(3) -0.016(3) N1 0.118(4) 0.083(3) 0.065(2) 0.001(2) -0.012(2) -0.009(2) C21 0.072(3) 0.103(3) 0.070(3) -0.003(2) -0.007(2) 0.000(3) C22 0.072(3) 0.095(3) 0.079(3) -0.015(2) -0.006(2) 0.022(2) C23 0.092(3) 0.061(3) 0.089(3) 0.003(2) -0.003(3) -0.009(2) C24 0.093(4) 0.134(5) 0.094(4) -0.053(3) -0.031(3) 0.018(3) C25 0.097(4) 0.130(4) 0.094(4) -0.041(3) 0.006(3) -0.039(3) C26 0.128(4) 0.077(3) 0.084(3) -0.003(2) -0.021(3) 0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O5 C2 1.369(3) . ? O5 C5 1.403(4) . ? C2 C7 1.373(4) . ? C2 C6 1.373(4) . ? C3 C8 1.369(4) . ? C3 C4 1.369(4) . ? C3 N2 1.464(4) . ? C4 C7 1.374(4) . ? C4 H4 0.9300 . ? C5 C10 1.353(4) . ? C5 C9 1.362(4) . ? C6 C8 1.372(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? O4 N2 1.215(4) . ? O3 N2 1.217(3) . ? C8 H8 0.9300 . ? C9 C11 1.377(4) . ? C9 H9 0.9300 . ? C10 C13 1.385(5) . ? C10 H10 0.9300 . ? C11 C12 1.346(5) . ? C11 H11 0.9300 . ? C12 C13 1.361(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? O6 C16 1.367(4) . ? O6 C17 1.389(4) . ? C15 C21 1.365(4) . ? C15 C19 1.367(4) . ? C15 N1 1.468(4) . ? C16 C22 1.374(4) . ? C16 C18 1.375(4) . ? C17 C20 1.351(4) . ? C17 C23 1.369(4) . ? C18 C19 1.383(4) . ? C18 H18 0.9300 . ? O2 N1 1.206(4) . ? C19 H19 0.9300 . ? O1 N1 1.221(4) . ? C20 C25 1.365(5) . ? C20 H20 0.9300 . ? C21 C22 1.368(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C26 1.367(5) . ? C23 H23 0.9300 . ? C24 C26 1.365(5) . ? C24 C25 1.369(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O5 C5 119.1(3) . . ? O5 C2 C7 124.3(3) . . ? O5 C2 C6 115.7(3) . . ? C7 C2 C6 120.0(3) . . ? C8 C3 C4 121.6(3) . . ? C8 C3 N2 118.5(4) . . ? C4 C3 N2 119.9(4) . . ? C3 C4 C7 118.9(3) . . ? C3 C4 H4 120.6 . . ? C7 C4 H4 120.6 . . ? C10 C5 C9 121.4(3) . . ? C10 C5 O5 119.0(4) . . ? C9 C5 O5 119.4(4) . . ? C8 C6 C2 120.2(3) . . ? C8 C6 H6 119.9 . . ? C2 C6 H6 119.9 . . ? C2 C7 C4 120.3(3) . . ? C2 C7 H7 119.9 . . ? C4 C7 H7 119.9 . . ? O4 N2 O3 123.5(4) . . ? O4 N2 C3 118.5(4) . . ? O3 N2 C3 118.0(4) . . ? C3 C8 C6 119.1(3) . . ? C3 C8 H8 120.5 . . ? C6 C8 H8 120.5 . . ? C5 C9 C11 119.3(3) . . ? C5 C9 H9 120.4 . . ? C11 C9 H9 120.4 . . ? C5 C10 C13 118.4(4) . . ? C5 C10 H10 120.8 . . ? C13 C10 H10 120.8 . . ? C12 C11 C9 120.2(4) . . ? C12 C11 H11 119.9 . . ? C9 C11 H11 119.9 . . ? C11 C12 C13 120.1(4) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C10 120.7(4) . . ? C12 C13 H13 119.7 . . ? C10 C13 H13 119.7 . . ? C16 O6 C17 118.9(3) . . ? C21 C15 C19 121.5(3) . . ? C21 C15 N1 119.2(4) . . ? C19 C15 N1 119.2(4) . . ? O6 C16 C22 115.5(3) . . ? O6 C16 C18 124.0(3) . . ? C22 C16 C18 120.5(4) . . ? C20 C17 C23 120.9(4) . . ? C20 C17 O6 118.6(4) . . ? C23 C17 O6 120.3(4) . . ? C16 C18 C19 119.5(3) . . ? C16 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C15 C19 C18 119.1(3) . . ? C15 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C17 C20 C25 119.4(4) . . ? C17 C20 H20 120.3 . . ? C25 C20 H20 120.3 . . ? O2 N1 O1 123.9(4) . . ? O2 N1 C15 118.5(4) . . ? O1 N1 C15 117.6(4) . . ? C15 C21 C22 119.5(4) . . ? C15 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C22 C16 119.9(4) . . ? C21 C22 H22 120.0 . . ? C16 C22 H22 120.0 . . ? C26 C23 C17 119.3(4) . . ? C26 C23 H23 120.4 . . ? C17 C23 H23 120.4 . . ? C26 C24 C25 119.0(4) . . ? C26 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C20 C25 C24 120.8(4) . . ? C20 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C24 C26 C23 120.6(4) . . ? C24 C26 H26 119.7 . . ? C23 C26 H26 119.7 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.123 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.032 # END# data_21 _database_code_depnum_ccdc_archive 'CCDC 265016' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-aminophenoxy)-N,N-dimethyl benzenamine ; _chemical_name_common '4-(4-aminophenoxy)-N,N-dimethyl benzenamine' _chemical_melting_point 369 _chemical_formula_moiety 'C14 H16 N2 O' _chemical_formula_sum 'C14 H16 N2 O' _chemical_formula_weight 228.29 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.0473(17) _cell_length_b 17.419(3) _cell_length_c 7.9560(15) _cell_angle_alpha 90.00 _cell_angle_beta 94.488(4) _cell_angle_gamma 90.00 _cell_volume 1250.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 559 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 21.00 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5455 _diffrn_reflns_av_R_equivalents 0.1207 _diffrn_reflns_av_sigmaI/netI 0.3158 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2318 _reflns_number_gt 559 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0046P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2318 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2356 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.0775 _refine_ls_wR_factor_gt 0.0545 _refine_ls_goodness_of_fit_ref 0.617 _refine_ls_restrained_S_all 0.617 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3829(3) 0.40686(15) 0.1225(3) 0.0934(10) Uani 1 1 d . . . C6 C 0.0437(4) 0.3805(2) -0.1615(5) 0.0647(11) Uani 1 1 d . . . H6 H -0.0515 0.4002 -0.1821 0.078 Uiso 1 1 calc R . . C4 C 0.2789(5) 0.3819(2) 0.0003(5) 0.0636(11) Uani 1 1 d . . . C3 C 0.3261(4) 0.3227(2) -0.0978(5) 0.0745(12) Uani 1 1 d . . . H3 H 0.4210 0.3028 -0.0763 0.089 Uiso 1 1 calc R . . N1 N 0.2525(3) 0.62324(18) 0.6107(4) 0.0836(10) Uani 1 1 d . . . C12 C 0.2583(4) 0.4417(2) 0.3699(5) 0.0785(12) Uani 1 1 d . . . H12 H 0.2197 0.3924 0.3750 0.094 Uiso 1 1 calc R . . N2 N -0.0059(5) 0.2899(2) -0.3889(5) 0.0992(14) Uani 1 1 d . . . C5 C 0.1382(5) 0.40999(18) -0.0327(5) 0.0639(11) Uani 1 1 d . . . H5 H 0.1056 0.4498 0.0330 0.077 Uiso 1 1 calc R . . C11 C 0.2307(4) 0.4946(2) 0.4929(4) 0.0791(12) Uani 1 1 d . . . H11 H 0.1729 0.4800 0.5791 0.095 Uiso 1 1 calc R . . C10 C 0.2865(4) 0.5690(2) 0.4918(5) 0.0640(10) Uani 1 1 d . . . C1 C 0.0924(6) 0.3204(2) -0.2613(5) 0.0699(12) Uani 1 1 d . . . C7 C 0.3426(4) 0.4614(3) 0.2398(5) 0.0742(12) Uani 1 1 d . . . C2 C 0.2345(5) 0.2935(2) -0.2257(5) 0.0771(14) Uani 1 1 d . . . H2 H 0.2689 0.2541 -0.2913 0.093 Uiso 1 1 calc R . . C9 C 0.3717(4) 0.5871(2) 0.3591(5) 0.0837(13) Uani 1 1 d . . . H9 H 0.4105 0.6363 0.3518 0.100 Uiso 1 1 calc R . . C8 C 0.3999(4) 0.5333(3) 0.2376(5) 0.0849(13) Uani 1 1 d . . . H8 H 0.4596 0.5467 0.1523 0.102 Uiso 1 1 calc R . . C13 C 0.3408(4) 0.69262(18) 0.6298(4) 0.1049(14) Uani 1 1 d . . . H13A H 0.4415 0.6794 0.6647 0.157 Uiso 1 1 calc R . . H13B H 0.3017 0.7250 0.7133 0.157 Uiso 1 1 calc R . . H13C H 0.3374 0.7194 0.5241 0.157 Uiso 1 1 calc R . . C14 C 0.1914(4) 0.59680(18) 0.7635(4) 0.1160(15) Uani 1 1 d . . . H14A H 0.1047 0.5663 0.7346 0.174 Uiso 1 1 calc R . . H14B H 0.1652 0.6402 0.8292 0.174 Uiso 1 1 calc R . . H14C H 0.2640 0.5663 0.8278 0.174 Uiso 1 1 calc R . . H1A H 0.045(4) 0.2581(18) -0.444(4) 0.108(18) Uiso 1 1 d . . . H1B H -0.094(4) 0.3180(19) -0.434(5) 0.14(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.081(2) 0.120(2) 0.080(2) -0.0330(18) 0.0098(18) 0.0209(18) C6 0.073(3) 0.059(3) 0.062(3) -0.003(2) 0.009(3) 0.004(2) C4 0.080(4) 0.059(3) 0.054(3) -0.011(2) 0.021(3) 0.007(3) C3 0.082(3) 0.072(3) 0.071(3) 0.008(2) 0.017(3) 0.022(3) N1 0.114(3) 0.079(3) 0.061(2) -0.015(2) 0.025(2) -0.025(2) C12 0.094(3) 0.069(3) 0.074(3) 0.000(3) 0.017(3) -0.017(3) N2 0.105(4) 0.094(3) 0.097(3) -0.034(3) 0.003(3) -0.001(3) C5 0.069(3) 0.060(3) 0.065(3) 0.001(2) 0.021(2) 0.013(3) C11 0.102(3) 0.080(3) 0.059(3) -0.010(3) 0.029(2) -0.022(3) C10 0.068(3) 0.066(3) 0.059(3) 0.006(2) 0.008(2) -0.018(2) C1 0.089(4) 0.062(3) 0.060(3) -0.008(2) 0.015(3) -0.010(3) C7 0.070(3) 0.089(4) 0.064(3) -0.007(3) 0.008(2) 0.008(3) C2 0.099(4) 0.057(3) 0.080(4) -0.005(2) 0.033(3) 0.013(3) C9 0.099(3) 0.079(3) 0.078(3) 0.004(3) 0.032(3) -0.021(3) C8 0.081(3) 0.106(4) 0.071(3) 0.012(3) 0.028(2) -0.009(3) C13 0.141(4) 0.079(3) 0.094(3) -0.018(2) 0.007(3) -0.050(3) C14 0.171(4) 0.102(3) 0.081(3) -0.023(3) 0.054(3) -0.033(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.370(4) . ? O1 C7 1.400(4) . ? C6 C5 1.381(4) . ? C6 C1 1.405(4) . ? C6 H6 0.9300 . ? C4 C5 1.370(4) . ? C4 C3 1.380(4) . ? C3 C2 1.360(4) . ? C3 H3 0.9300 . ? N1 C10 1.388(4) . ? N1 C14 1.449(3) . ? N1 C13 1.450(3) . ? C12 C7 1.376(4) . ? C12 C11 1.381(3) . ? C12 H12 0.9300 . ? N2 C1 1.400(5) . ? N2 H1A 0.87(3) . ? N2 H1B 0.98(3) . ? C5 H5 0.9300 . ? C11 C10 1.392(3) . ? C11 H11 0.9300 . ? C10 C9 1.391(4) . ? C1 C2 1.376(4) . ? C7 C8 1.355(4) . ? C2 H2 0.9300 . ? C9 C8 1.385(4) . ? C9 H9 0.9300 . ? C8 H8 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C7 119.2(3) . . ? C5 C6 C1 119.6(4) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C5 C4 O1 126.8(4) . . ? C5 C4 C3 118.8(4) . . ? O1 C4 C3 114.4(4) . . ? C2 C3 C4 120.4(4) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C10 N1 C14 118.4(3) . . ? C10 N1 C13 119.2(3) . . ? C14 N1 C13 114.8(3) . . ? C7 C12 C11 120.6(4) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C1 N2 H1A 106(2) . . ? C1 N2 H1B 122(2) . . ? H1A N2 H1B 126(3) . . ? C4 C5 C6 121.4(4) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C12 C11 C10 122.1(3) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? N1 C10 C9 121.9(4) . . ? N1 C10 C11 122.0(4) . . ? C9 C10 C11 116.0(4) . . ? C2 C1 N2 123.4(5) . . ? C2 C1 C6 117.8(4) . . ? N2 C1 C6 118.8(5) . . ? C8 C7 C12 118.4(4) . . ? C8 C7 O1 119.9(4) . . ? C12 C7 O1 121.4(4) . . ? C3 C2 C1 122.1(4) . . ? C3 C2 H2 119.0 . . ? C1 C2 H2 119.0 . . ? C8 C9 C10 121.3(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C7 C8 C9 121.7(4) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.094 _refine_diff_density_min -0.095 _refine_diff_density_rms 0.024 # END# data_22 _database_code_depnum_ccdc_archive 'CCDC 265017' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-Methoxyphenoxy)benzoic acid ; _chemical_name_common '4-(4-Methoxyphenoxy)benzoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 O4' _chemical_formula_sum 'C14 H12 O4' _chemical_formula_weight 244.24 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.4742(11) _cell_length_b 5.9733(8) _cell_length_c 53.194(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2374.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2740 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 25.01 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10783 _diffrn_reflns_av_R_equivalents 0.0550 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -63 _diffrn_reflns_limit_l_max 62 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2087 _reflns_number_gt 1475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+1.5038P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2087 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1065 _refine_ls_R_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1484 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0098(3) 1.1109(3) 0.87641(3) 0.0466(6) Uani 1 1 d . . . C5 C -0.0801(4) 0.7838(5) 0.90067(5) 0.0409(8) Uani 1 1 d . . . H5 H -0.1331 0.7169 0.8867 0.049 Uiso 1 1 calc R . . C3 C 0.0797(4) 1.0905(5) 0.91912(6) 0.0431(8) Uani 1 1 d . . . H3 H 0.1357 1.2287 0.9175 0.052 Uiso 1 1 calc R . . C8 C 0.0942(4) 0.8129(5) 0.84759(5) 0.0430(8) Uani 1 1 d . . . H8 H 0.1587 0.7399 0.8601 0.052 Uiso 1 1 calc R . . C6 C -0.0846(4) 0.6805(5) 0.92380(5) 0.0400(8) Uani 1 1 d . . . H6 H -0.1401 0.5418 0.9254 0.048 Uiso 1 1 calc R . . C2 C 0.0719(4) 0.9876(5) 0.94213(6) 0.0428(8) Uani 1 1 d . . . H2 H 0.1208 1.0582 0.9561 0.051 Uiso 1 1 calc R . . C12 C -0.0919(4) 1.1156(5) 0.83460(6) 0.0422(8) Uani 1 1 d . . . H12 H -0.1542 1.2461 0.8384 0.051 Uiso 1 1 calc R . . C1 C -0.0083(4) 0.7788(5) 0.94475(5) 0.0401(8) Uani 1 1 d . . . C11 C -0.0935(4) 1.0322(5) 0.81061(6) 0.0462(8) Uani 1 1 d . . . H11 H -0.1565 1.1069 0.7981 0.055 Uiso 1 1 calc R . . C9 C 0.0910(4) 0.7271(5) 0.82352(5) 0.0439(8) Uani 1 1 d . . . H9 H 0.1515 0.5950 0.8199 0.053 Uiso 1 1 calc R . . C4 C 0.0046(4) 0.9889(5) 0.89852(5) 0.0381(7) Uani 1 1 d . . . C7 C 0.0023(4) 1.0055(5) 0.85314(5) 0.0382(7) Uani 1 1 d . . . C10 C -0.0017(4) 0.8369(5) 0.80487(5) 0.0412(8) Uani 1 1 d . . . O3 O -0.0885(4) 0.4793(4) 0.97104(4) 0.0696(8) Uani 1 1 d . . . C13 C -0.0095(5) 0.6605(6) 0.96911(6) 0.0483(8) Uani 1 1 d . . . O4 O -0.0142(3) 0.7672(4) 0.78041(4) 0.0588(7) Uani 1 1 d . . . O2 O 0.0793(4) 0.7507(5) 0.98686(5) 0.0702(8) Uani 1 1 d . . . C14 C 0.0827(6) 0.5730(7) 0.77335(6) 0.0771(13) Uani 1 1 d . . . H14A H 0.2080 0.5971 0.7762 0.116 Uiso 1 1 calc R . . H14B H 0.0629 0.5426 0.7558 0.116 Uiso 1 1 calc R . . H14C H 0.0427 0.4479 0.7832 0.116 Uiso 1 1 calc R . . H1A H 0.078(7) 0.657(11) 1.0055(12) 0.19(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0602(14) 0.0405(12) 0.0391(13) 0.0009(10) 0.0024(10) -0.0008(11) C5 0.0395(18) 0.047(2) 0.0358(16) -0.0033(15) -0.0053(14) -0.0049(16) C3 0.0412(18) 0.0395(18) 0.0486(19) -0.0057(15) 0.0032(15) -0.0057(15) C8 0.0405(18) 0.0475(19) 0.0411(17) 0.0061(15) -0.0022(14) 0.0081(16) C6 0.0418(18) 0.0364(17) 0.0418(18) -0.0021(14) 0.0002(14) -0.0036(15) C2 0.0444(18) 0.0424(19) 0.0418(18) -0.0081(15) -0.0018(14) -0.0018(16) C12 0.0409(19) 0.0380(18) 0.0477(19) 0.0035(15) 0.0033(15) 0.0055(15) C1 0.0403(18) 0.0436(19) 0.0365(17) -0.0042(14) 0.0004(14) 0.0053(16) C11 0.044(2) 0.047(2) 0.0474(19) 0.0141(16) -0.0027(15) 0.0038(17) C9 0.049(2) 0.0402(18) 0.0424(18) 0.0040(15) 0.0039(15) 0.0064(16) C4 0.0330(16) 0.0417(18) 0.0397(17) 0.0017(15) 0.0031(14) 0.0056(15) C7 0.0354(16) 0.0414(17) 0.0378(17) 0.0035(14) 0.0020(14) -0.0053(15) C10 0.0438(18) 0.0464(19) 0.0334(16) 0.0043(15) 0.0036(14) -0.0052(16) O3 0.097(2) 0.0641(17) 0.0474(14) 0.0103(13) -0.0108(13) -0.0269(16) C13 0.054(2) 0.048(2) 0.044(2) -0.0049(16) -0.0010(17) -0.0021(18) O4 0.0743(17) 0.0657(16) 0.0364(13) 0.0008(12) -0.0038(11) 0.0053(14) O2 0.097(2) 0.0709(17) 0.0427(14) 0.0005(13) -0.0174(14) -0.0223(16) C14 0.113(4) 0.069(3) 0.049(2) -0.016(2) 0.002(2) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.384(3) . ? O1 C7 1.390(3) . ? C5 C6 1.377(4) . ? C5 C4 1.384(4) . ? C5 H5 0.9300 . ? C3 C2 1.370(4) . ? C3 C4 1.373(4) . ? C3 H3 0.9300 . ? C8 C7 1.372(4) . ? C8 C9 1.379(4) . ? C8 H8 0.9300 . ? C6 C1 1.383(4) . ? C6 H6 0.9300 . ? C2 C1 1.391(4) . ? C2 H2 0.9300 . ? C12 C11 1.370(4) . ? C12 C7 1.379(4) . ? C12 H12 0.9300 . ? C1 C13 1.476(4) . ? C11 C10 1.387(4) . ? C11 H11 0.9300 . ? C9 C10 1.377(4) . ? C9 H9 0.9300 . ? C10 O4 1.369(3) . ? O3 C13 1.237(4) . ? C13 O2 1.274(4) . ? O4 C14 1.418(4) . ? O2 H1A 1.14(7) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 C7 121.1(2) . . ? C6 C5 C4 118.8(3) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C7 C8 C9 120.2(3) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C5 C6 C1 121.3(3) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C11 C12 C7 119.8(3) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C6 C1 C2 118.5(3) . . ? C6 C1 C13 120.1(3) . . ? C2 C1 C13 121.3(3) . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C10 C9 C8 120.1(3) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C3 C4 O1 115.7(3) . . ? C3 C4 C5 120.8(3) . . ? O1 C4 C5 123.3(3) . . ? C8 C7 C12 120.1(3) . . ? C8 C7 O1 123.4(3) . . ? C12 C7 O1 116.2(3) . . ? O4 C10 C9 125.1(3) . . ? O4 C10 C11 115.6(3) . . ? C9 C10 C11 119.4(3) . . ? O3 C13 O2 123.9(3) . . ? O3 C13 C1 119.7(3) . . ? O2 C13 C1 116.4(3) . . ? C10 O4 C14 117.8(3) . . ? C13 O2 H1A 116(3) . . ? O4 C14 H14A 109.5 . . ? O4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.179 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.047 # END# data_23 _database_code_depnum_ccdc_archive 'CCDC 265018' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-dimethyl-p-(p-hydroxyphenoxy) aniline ; _chemical_name_common 'N,N-dimethyl-p-(p-hydroxyphenoxy) aniline' _chemical_melting_point 411 _chemical_formula_moiety 'C14 H15 N O2' _chemical_formula_sum 'C14 H15 N O2' _chemical_formula_weight 229.27 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.654(4) _cell_length_b 13.836(3) _cell_length_c 9.885(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.084(3) _cell_angle_gamma 90.00 _cell_volume 2525.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2187 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 24.69 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6972 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2224 _reflns_number_gt 1446 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+0.3002P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2224 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0804 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.20189(7) 0.48916(10) 0.19569(15) 0.0747(5) Uani 1 1 d . . . O1 O 0.05718(10) 0.15701(11) 0.00615(18) 0.0783(5) Uani 1 1 d . . . C1 C 0.08948(11) 0.24128(14) 0.0550(2) 0.0566(5) Uani 1 1 d . . . C2 C 0.12333(10) 0.76370(14) 0.07842(19) 0.0538(5) Uani 1 1 d . . . C3 C 0.17353(10) 0.57980(14) 0.1546(2) 0.0577(5) Uani 1 1 d . . . N1 N 0.09273(9) 0.85548(12) 0.03931(16) 0.0625(5) Uani 1 1 d . . . C4 C 0.19933(11) 0.32417(15) 0.1375(2) 0.0607(5) Uani 1 1 d . . . H4 H 0.2493 0.3231 0.1622 0.073 Uiso 1 1 calc R . . C5 C 0.14433(12) 0.63689(15) 0.2454(2) 0.0665(6) Uani 1 1 d . . . H5 H 0.1414 0.6143 0.3331 0.080 Uiso 1 1 calc R . . C6 C 0.16321(12) 0.24087(15) 0.0929(2) 0.0617(6) Uani 1 1 d . . . H6 H 0.1890 0.1837 0.0884 0.074 Uiso 1 1 calc R . . C7 C 0.17786(11) 0.61347(16) 0.0260(2) 0.0687(6) Uani 1 1 d . . . H7 H 0.1974 0.5745 -0.0363 0.082 Uiso 1 1 calc R . . C8 C 0.11933(11) 0.72765(15) 0.20729(19) 0.0636(6) Uani 1 1 d . . . H8 H 0.0992 0.7657 0.2698 0.076 Uiso 1 1 calc R . . C9 C 0.16188(11) 0.40846(14) 0.14557(19) 0.0554(5) Uani 1 1 d . . . C10 C 0.15337(11) 0.70491(16) -0.0117(2) 0.0676(6) Uani 1 1 d . . . H10 H 0.1571 0.7274 -0.0991 0.081 Uiso 1 1 calc R . . C11 C 0.05219(11) 0.32597(15) 0.0654(2) 0.0680(6) Uani 1 1 d . . . H11 H 0.0021 0.3269 0.0420 0.082 Uiso 1 1 calc R . . C12 C 0.08822(11) 0.40966(15) 0.1102(2) 0.0666(6) Uani 1 1 d . . . H12 H 0.0625 0.4667 0.1164 0.080 Uiso 1 1 calc R . . C13 C 0.10383(15) 0.93033(16) 0.1446(3) 0.0998(9) Uani 1 1 d . . . H13A H 0.0865 0.9076 0.2259 0.150 Uiso 1 1 calc R . . H13B H 0.0778 0.9876 0.1123 0.150 Uiso 1 1 calc R . . H13C H 0.1545 0.9449 0.1647 0.150 Uiso 1 1 calc R . . C14 C 0.10591(14) 0.89258(18) -0.0938(3) 0.0993(9) Uani 1 1 d . . . H14A H 0.1570 0.9008 -0.0938 0.149 Uiso 1 1 calc R . . H14B H 0.0820 0.9537 -0.1108 0.149 Uiso 1 1 calc R . . H14C H 0.0874 0.8476 -0.1640 0.149 Uiso 1 1 calc R . . H1A H 0.0093(16) 0.1577(19) -0.007(3) 0.126(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0672(10) 0.0602(10) 0.0877(11) -0.0039(8) -0.0205(8) 0.0039(8) O1 0.0761(12) 0.0507(10) 0.1078(14) -0.0053(8) 0.0118(10) -0.0016(8) C1 0.0637(13) 0.0495(13) 0.0576(12) 0.0034(9) 0.0117(10) 0.0012(10) C2 0.0534(12) 0.0539(12) 0.0522(12) -0.0026(9) 0.0013(10) -0.0081(9) C3 0.0518(12) 0.0521(13) 0.0644(14) -0.0043(10) -0.0088(10) -0.0021(10) N1 0.0739(11) 0.0527(11) 0.0592(11) 0.0029(8) 0.0033(9) -0.0024(9) C4 0.0522(12) 0.0656(14) 0.0628(13) 0.0005(10) 0.0030(10) 0.0092(11) C5 0.0860(15) 0.0642(14) 0.0473(12) 0.0012(10) 0.0031(11) -0.0005(12) C6 0.0640(14) 0.0558(13) 0.0658(14) 0.0022(10) 0.0106(11) 0.0161(11) C7 0.0704(14) 0.0730(16) 0.0634(14) -0.0118(12) 0.0121(11) 0.0076(12) C8 0.0825(15) 0.0593(13) 0.0493(12) -0.0057(10) 0.0101(11) 0.0017(11) C9 0.0560(13) 0.0548(13) 0.0536(12) -0.0005(9) 0.0007(10) 0.0034(10) C10 0.0796(15) 0.0723(15) 0.0529(12) 0.0030(11) 0.0161(12) 0.0022(12) C11 0.0527(12) 0.0588(14) 0.0906(16) -0.0040(11) 0.0037(11) 0.0028(11) C12 0.0561(13) 0.0537(14) 0.0880(16) -0.0073(11) 0.0032(11) 0.0097(10) C13 0.132(2) 0.0566(16) 0.102(2) -0.0113(13) -0.0159(17) 0.0074(15) C14 0.113(2) 0.0970(19) 0.0919(19) 0.0368(15) 0.0267(17) 0.0140(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C9 1.395(2) . ? O2 C3 1.399(2) . ? O1 C1 1.369(2) . ? O1 H1A 0.88(3) . ? C1 C11 1.374(3) . ? C1 C6 1.374(3) . ? C2 C8 1.380(3) . ? C2 C10 1.382(3) . ? C2 N1 1.423(2) . ? C3 C5 1.365(3) . ? C3 C7 1.367(3) . ? N1 C13 1.462(3) . ? N1 C14 1.465(3) . ? C4 C9 1.368(3) . ? C4 C6 1.376(3) . ? C4 H4 0.9300 . ? C5 C8 1.374(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C10 1.379(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C12 1.370(3) . ? C10 H10 0.9300 . ? C11 C12 1.380(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O2 C3 116.94(15) . . ? C1 O1 H1A 115.4(18) . . ? O1 C1 C11 123.40(19) . . ? O1 C1 C6 117.83(18) . . ? C11 C1 C6 118.75(19) . . ? C8 C2 C10 117.52(19) . . ? C8 C2 N1 120.10(17) . . ? C10 C2 N1 122.24(18) . . ? C5 C3 C7 119.71(19) . . ? C5 C3 O2 119.82(19) . . ? C7 C3 O2 120.40(18) . . ? C2 N1 C13 115.30(16) . . ? C2 N1 C14 116.42(17) . . ? C13 N1 C14 111.49(19) . . ? C9 C4 C6 120.13(19) . . ? C9 C4 H4 119.9 . . ? C6 C4 H4 119.9 . . ? C3 C5 C8 119.98(19) . . ? C3 C5 H5 120.0 . . ? C8 C5 H5 120.0 . . ? C1 C6 C4 120.69(18) . . ? C1 C6 H6 119.7 . . ? C4 C6 H6 119.7 . . ? C3 C7 C10 120.23(19) . . ? C3 C7 H7 119.9 . . ? C10 C7 H7 119.9 . . ? C5 C8 C2 121.57(19) . . ? C5 C8 H8 119.2 . . ? C2 C8 H8 119.2 . . ? C4 C9 C12 119.86(19) . . ? C4 C9 O2 116.83(18) . . ? C12 C9 O2 123.26(17) . . ? C7 C10 C2 120.98(19) . . ? C7 C10 H10 119.5 . . ? C2 C10 H10 119.5 . . ? C1 C11 C12 120.7(2) . . ? C1 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C9 C12 C11 119.83(19) . . ? C9 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? N1 C13 H13A 109.5 . . ? N1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C14 H14A 109.5 . . ? N1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.137 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.038 # END# data_24 _database_code_depnum_ccdc_archive 'CCDC 265019' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Amino-4'-cyanodiphenyl ether ; _chemical_name_common "4-Amino-4'-cyanodiphenyl ether" _chemical_melting_point 379 _chemical_formula_moiety 'C13 H10 N2 O' _chemical_formula_sum 'C13 H10 N2 O' _chemical_formula_weight 210.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M ' P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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' _cell_length_a 11.6484(19) _cell_length_b 5.6103(10) _cell_length_c 16.746(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.581(3) _cell_angle_gamma 90.00 _cell_volume 1075.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1294 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.00 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5240 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0687 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1887 _reflns_number_gt 1121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.3348P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1887 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1370 _refine_ls_R_factor_gt 0.0803 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.77632(19) 0.1158(4) 0.86821(15) 0.0663(8) Uani 1 1 d . . . C1 C 1.0767(3) 0.0985(6) 0.76580(19) 0.0463(8) Uani 1 1 d . . . C14 C 1.0526(3) -0.0807(6) 0.8166(2) 0.0529(9) Uani 1 1 d . . . H14 H 1.1029 -0.2104 0.8271 0.064 Uiso 1 1 calc R . . C3 C 0.8806(3) 0.1203(6) 0.8375(2) 0.0495(9) Uani 1 1 d . . . N1 N 1.1752(3) 0.0900(7) 0.7291(2) 0.0647(9) Uani 1 1 d . . . C16 C 0.9036(3) 0.3004(6) 0.7879(2) 0.0569(10) Uani 1 1 d . . . H16 H 0.8530 0.4294 0.7776 0.068 Uiso 1 1 calc R . . C18 C 0.7534(3) 0.3080(6) 0.9140(2) 0.0484(9) Uani 1 1 d . . . C15 C 0.9547(3) -0.0702(6) 0.8523(2) 0.0544(9) Uani 1 1 d . . . H15 H 0.9393 -0.1925 0.8863 0.065 Uiso 1 1 calc R . . C7 C 0.6648(3) 0.8780(7) 1.0516(2) 0.0632(10) Uani 1 1 d . . . C22 C 0.8369(3) 0.4049(6) 0.9738(2) 0.0563(10) Uani 1 1 d . . . H22 H 0.9127 0.3454 0.9829 0.068 Uiso 1 1 calc R . . C9 C 0.6956(3) 0.6815(6) 1.0057(2) 0.0520(9) Uani 1 1 d . . . C17 C 1.0015(3) 0.2909(6) 0.7533(2) 0.0559(9) Uani 1 1 d . . . H17 H 1.0175 0.4165 0.7208 0.067 Uiso 1 1 calc R . . C19 C 0.6414(3) 0.3932(7) 0.9004(2) 0.0655(11) Uani 1 1 d . . . H19 H 0.5848 0.3246 0.8606 0.079 Uiso 1 1 calc R . . C21 C 0.8081(3) 0.5900(6) 1.0201(2) 0.0575(10) Uani 1 1 d . . . H21 H 0.8642 0.6541 1.0613 0.069 Uiso 1 1 calc R . . C20 C 0.6131(3) 0.5804(7) 0.9458(2) 0.0657(11) Uani 1 1 d . . . H20 H 0.5373 0.6398 0.9360 0.079 Uiso 1 1 calc R . . N2 N 0.6389(3) 1.0359(7) 1.0872(2) 0.0862(12) Uani 1 1 d . . . H2A H 1.167(3) 0.166(7) 0.682(2) 0.082(14) Uiso 1 1 d . . . H1A H 1.212(3) -0.054(7) 0.734(2) 0.077(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0590(15) 0.0571(17) 0.086(2) -0.0195(14) 0.0217(14) -0.0101(12) C1 0.056(2) 0.041(2) 0.041(2) -0.0021(17) 0.0048(16) -0.0025(18) C14 0.053(2) 0.042(2) 0.063(2) 0.0074(18) 0.0081(18) 0.0070(17) C3 0.055(2) 0.042(2) 0.050(2) -0.0082(18) 0.0055(17) -0.0044(18) N1 0.070(2) 0.062(2) 0.064(2) 0.0132(19) 0.0198(18) 0.0081(19) C16 0.071(2) 0.041(2) 0.057(2) 0.0006(19) 0.006(2) 0.0117(18) C18 0.053(2) 0.048(2) 0.045(2) -0.0030(18) 0.0130(17) -0.0018(18) C15 0.065(2) 0.038(2) 0.059(2) 0.0108(18) 0.0091(18) -0.0045(18) C7 0.062(2) 0.078(3) 0.051(2) -0.003(2) 0.0147(19) 0.009(2) C22 0.0420(18) 0.066(3) 0.059(2) -0.007(2) 0.0044(17) 0.0042(18) C9 0.056(2) 0.059(2) 0.043(2) 0.0007(18) 0.0123(17) 0.0060(18) C17 0.077(2) 0.041(2) 0.050(2) 0.0082(18) 0.0136(19) 0.003(2) C19 0.054(2) 0.077(3) 0.059(3) -0.014(2) -0.0059(18) 0.004(2) C21 0.054(2) 0.069(3) 0.049(2) -0.0093(19) 0.0076(17) -0.0028(19) C20 0.054(2) 0.081(3) 0.060(3) -0.007(2) 0.0050(19) 0.017(2) N2 0.090(2) 0.096(3) 0.074(3) -0.022(2) 0.018(2) 0.022(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C18 1.377(4) . ? O1 C3 1.404(4) . ? C1 C14 1.379(4) . ? C1 C17 1.382(4) . ? C1 N1 1.398(4) . ? C14 C15 1.382(4) . ? C14 H14 0.9300 . ? C3 C16 1.366(4) . ? C3 C15 1.368(4) . ? N1 H2A 0.89(4) . ? N1 H1A 0.91(4) . ? C16 C17 1.371(4) . ? C16 H16 0.9300 . ? C18 C19 1.369(4) . ? C18 C22 1.375(4) . ? C15 H15 0.9300 . ? C7 N2 1.140(4) . ? C7 C9 1.427(5) . ? C22 C21 1.374(4) . ? C22 H22 0.9300 . ? C9 C20 1.377(5) . ? C9 C21 1.387(4) . ? C17 H17 0.9300 . ? C19 C20 1.372(5) . ? C19 H19 0.9300 . ? C21 H21 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 O1 C3 117.3(3) . . ? C14 C1 C17 117.9(3) . . ? C14 C1 N1 121.5(3) . . ? C17 C1 N1 120.6(3) . . ? C1 C14 C15 120.9(3) . . ? C1 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C3 C15 120.1(3) . . ? C16 C3 O1 121.1(3) . . ? C15 C3 O1 118.6(3) . . ? C1 N1 H2A 115(2) . . ? C1 N1 H1A 113(2) . . ? H2A N1 H1A 119(4) . . ? C3 C16 C17 120.0(3) . . ? C3 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C19 C18 C22 120.6(3) . . ? C19 C18 O1 117.2(3) . . ? C22 C18 O1 122.1(3) . . ? C3 C15 C14 119.9(3) . . ? C3 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N2 C7 C9 178.9(4) . . ? C21 C22 C18 119.8(3) . . ? C21 C22 H22 120.1 . . ? C18 C22 H22 120.1 . . ? C20 C9 C21 119.0(3) . . ? C20 C9 C7 120.0(3) . . ? C21 C9 C7 121.0(3) . . ? C16 C17 C1 121.3(3) . . ? C16 C17 H17 119.3 . . ? C1 C17 H17 119.3 . . ? C18 C19 C20 119.6(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C22 C21 C9 120.1(3) . . ? C22 C21 H21 119.9 . . ? C9 C21 H21 119.9 . . ? C19 C20 C9 120.9(3) . . ? C19 C20 H20 119.6 . . ? C9 C20 H20 119.6 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.164 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.035 # END# data_25 _database_code_depnum_ccdc_archive 'CCDC 265020' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(4-methoxyphenoxy)-N,N-dimethyl-aniline ; _chemical_name_common 4-(4-methoxyphenoxy)-N,N-dimethyl-aniline _chemical_melting_point ? _chemical_formula_moiety 'C15 H17 N O2' _chemical_formula_sum 'C15 H17 N O2' _chemical_formula_weight 243.30 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'Cc ' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 28.046(5) _cell_length_b 7.5638(14) _cell_length_c 6.3222(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.738(2) _cell_angle_gamma 90.00 _cell_volume 1331.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2563 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 26.04 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7152 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2337 _reflns_number_gt 1641 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+0.0114P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.3(15) _refine_ls_number_reflns 2337 _refine_ls_number_parameters 166 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.12770(5) 0.2597(3) 1.0029(2) 0.0659(5) Uani 1 1 d . . . C1 C -0.00869(9) 0.2445(4) 0.6519(4) 0.0545(7) Uani 1 1 d . . . C2 C 0.25800(8) 0.2488(3) 0.7567(4) 0.0557(7) Uani 1 1 d . . . C3 C 0.04784(9) 0.1550(4) 0.9508(4) 0.0572(7) Uani 1 1 d . . . H3 H 0.0543 0.0913 1.0767 0.069 Uiso 1 1 calc R . . O2 O 0.30326(6) 0.2530(3) 0.6933(3) 0.0761(6) Uani 1 1 d . . . C5 C 0.17516(9) 0.1639(4) 0.7271(4) 0.0597(7) Uani 1 1 d . . . H5 H 0.1492 0.1040 0.6551 0.072 Uiso 1 1 calc R . . C6 C 0.07342(9) 0.3467(4) 0.6897(4) 0.0603(7) Uani 1 1 d . . . H6 H 0.0973 0.4143 0.6389 0.072 Uiso 1 1 calc R . . N1 N -0.05387(9) 0.2357(4) 0.5369(4) 0.0751(7) Uani 1 1 d . . . C8 C 0.02837(9) 0.3422(4) 0.5802(4) 0.0624(7) Uani 1 1 d . . . H8 H 0.0223 0.4061 0.4542 0.075 Uiso 1 1 calc R . . C9 C 0.25197(9) 0.3400(4) 0.9393(4) 0.0605(7) Uani 1 1 d . . . H9 H 0.2779 0.3998 1.0121 0.073 Uiso 1 1 calc R . . C10 C 0.20813(9) 0.3440(4) 1.0157(4) 0.0574(7) Uani 1 1 d . . . H10 H 0.2045 0.4058 1.1400 0.069 Uiso 1 1 calc R . . C12 C 0.00260(9) 0.1519(4) 0.8417(4) 0.0614(7) Uani 1 1 d . . . H12 H -0.0212 0.0861 0.8959 0.074 Uiso 1 1 calc R . . C13 C 0.21965(9) 0.1593(4) 0.6506(4) 0.0616(8) Uani 1 1 d . . . H13 H 0.2235 0.0958 0.5277 0.074 Uiso 1 1 calc R . . C14 C 0.16963(8) 0.2569(3) 0.9088(4) 0.0532(7) Uani 1 1 d . . . C15 C -0.06486(12) 0.3471(5) 0.3558(5) 0.0913(10) Uani 1 1 d . . . H15A H -0.0607 0.4685 0.3982 0.137 Uiso 1 1 calc R . . H15B H -0.0975 0.3279 0.2960 0.137 Uiso 1 1 calc R . . H15C H -0.0438 0.3198 0.2512 0.137 Uiso 1 1 calc R . . C16 C 0.08340(8) 0.2506(4) 0.8761(4) 0.0532(7) Uani 1 1 d . . . C17 C 0.31001(10) 0.1644(5) 0.5038(5) 0.0957(11) Uani 1 1 d . . . H17A H 0.2898 0.2162 0.3872 0.144 Uiso 1 1 calc R . . H17B H 0.3019 0.0418 0.5164 0.144 Uiso 1 1 calc R . . H17C H 0.3430 0.1745 0.4784 0.144 Uiso 1 1 calc R . . C19 C -0.09329(11) 0.1614(5) 0.6310(5) 0.0898(10) Uani 1 1 d . . . H19A H -0.0855 0.0428 0.6770 0.135 Uiso 1 1 calc R . . H19B H -0.1213 0.1598 0.5281 0.135 Uiso 1 1 calc R . . H19C H -0.0995 0.2316 0.7513 0.135 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0511(11) 0.0861(14) 0.0601(11) -0.0045(10) 0.0047(9) 0.0032(9) C1 0.0485(16) 0.0524(17) 0.0642(17) 0.0009(15) 0.0133(14) 0.0035(14) C2 0.0444(16) 0.0655(19) 0.0554(16) 0.0064(14) -0.0020(13) 0.0002(14) C3 0.0553(17) 0.0628(19) 0.0552(14) 0.0060(14) 0.0137(13) 0.0015(15) O2 0.0484(12) 0.1096(19) 0.0702(12) -0.0035(11) 0.0069(9) -0.0067(10) C5 0.0471(15) 0.0673(19) 0.0627(16) -0.0089(16) -0.0017(12) -0.0055(14) C6 0.0511(16) 0.0623(17) 0.0692(17) 0.0101(16) 0.0145(13) -0.0045(14) N1 0.0477(14) 0.092(2) 0.0842(17) 0.0113(16) 0.0019(12) -0.0005(13) C8 0.0553(16) 0.070(2) 0.0626(16) 0.0152(16) 0.0087(13) 0.0027(17) C9 0.0527(17) 0.067(2) 0.0577(16) -0.0051(17) -0.0129(13) -0.0054(15) C10 0.0551(17) 0.0640(19) 0.0506(13) -0.0073(15) -0.0045(13) 0.0026(15) C12 0.0518(16) 0.0672(19) 0.0683(17) 0.0083(16) 0.0205(13) -0.0021(15) C13 0.0557(17) 0.067(2) 0.0612(16) -0.0109(16) 0.0016(14) 0.0033(15) C14 0.0503(15) 0.0525(19) 0.0558(17) 0.0047(15) 0.0023(13) 0.0065(14) C15 0.069(2) 0.113(3) 0.086(2) 0.010(2) -0.0138(16) 0.0018(19) C16 0.0470(14) 0.0584(17) 0.0545(15) -0.0048(15) 0.0065(12) 0.0074(14) C17 0.0553(17) 0.166(3) 0.0674(18) -0.007(2) 0.0128(15) -0.0034(19) C19 0.0546(17) 0.116(3) 0.101(2) 0.000(2) 0.0170(16) -0.0059(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C14 1.379(3) . ? O1 C16 1.399(3) . ? C1 N1 1.387(3) . ? C1 C12 1.393(3) . ? C1 C8 1.394(3) . ? C2 C9 1.372(4) . ? C2 O2 1.376(3) . ? C2 C13 1.377(3) . ? C3 C16 1.361(3) . ? C3 C12 1.371(3) . ? C3 H3 0.9300 . ? O2 C17 1.405(3) . ? C5 C14 1.371(3) . ? C5 C13 1.390(3) . ? C5 H5 0.9300 . ? C6 C8 1.368(3) . ? C6 C16 1.385(3) . ? C6 H6 0.9300 . ? N1 C15 1.426(4) . ? N1 C19 1.431(3) . ? C8 H8 0.9300 . ? C9 C10 1.373(3) . ? C9 H9 0.9300 . ? C10 C14 1.374(3) . ? C10 H10 0.9300 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 O1 C16 119.79(19) . . ? N1 C1 C12 121.9(2) . . ? N1 C1 C8 121.7(2) . . ? C12 C1 C8 116.4(3) . . ? C9 C2 O2 116.3(2) . . ? C9 C2 C13 119.4(2) . . ? O2 C2 C13 124.3(3) . . ? C16 C3 C12 120.5(2) . . ? C16 C3 H3 119.8 . . ? C12 C3 H3 119.8 . . ? C2 O2 C17 117.3(2) . . ? C14 C5 C13 119.9(2) . . ? C14 C5 H5 120.0 . . ? C13 C5 H5 120.0 . . ? C8 C6 C16 120.0(2) . . ? C8 C6 H6 120.0 . . ? C16 C6 H6 120.0 . . ? C1 N1 C15 119.4(2) . . ? C1 N1 C19 120.2(2) . . ? C15 N1 C19 117.5(3) . . ? C6 C8 C1 121.9(3) . . ? C6 C8 H8 119.1 . . ? C1 C8 H8 119.1 . . ? C2 C9 C10 120.7(2) . . ? C2 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C14 120.1(2) . . ? C9 C10 H10 120.0 . . ? C14 C10 H10 120.0 . . ? C3 C12 C1 121.8(2) . . ? C3 C12 H12 119.1 . . ? C1 C12 H12 119.1 . . ? C2 C13 C5 120.0(3) . . ? C2 C13 H13 120.0 . . ? C5 C13 H13 120.0 . . ? C5 C14 C10 119.9(2) . . ? C5 C14 O1 123.8(2) . . ? C10 C14 O1 116.2(2) . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C3 C16 C6 119.4(2) . . ? C3 C16 O1 117.7(2) . . ? C6 C16 O1 122.6(2) . . ? O2 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.109 _refine_diff_density_min -0.116 _refine_diff_density_rms 0.025 # END# data_26 _database_code_depnum_ccdc_archive 'CCDC 265021' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ' ?' _chemical_melting_point 430 _chemical_formula_moiety 'C20 H17 N O3' _chemical_formula_sum 'C20 H17 N O3' _chemical_formula_weight 319.35 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M ' P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 6.137(2) _cell_length_b 7.451(2) _cell_length_c 34.981(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1599.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.83 _cell_measurement_theta_max 11.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.64 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius Mach3 four-circle' _diffrn_measurement_method 'Profile data from omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% ? _diffrn_reflns_number 2736 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1431 _reflns_number_gt 1278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction ' WinGX (Farrugia, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.1025P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(14) _refine_ls_number_reflns 1431 _refine_ls_number_parameters 223 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.4726(3) -0.4957(3) 1.00751(5) 0.0466(5) Uani 1 1 d . . . C10 C 0.3604(4) -0.4128(3) 0.90786(6) 0.0368(6) Uani 1 1 d . . . H10 H 0.4296 -0.3566 0.8875 0.044 Uiso 1 1 calc R . . O1 O -0.4492(3) -0.4808(3) 0.70781(5) 0.0492(5) Uani 1 1 d . . . C20 C 0.1759(5) -0.4119(4) 1.05038(7) 0.0444(7) Uani 1 1 d . . . H20 H 0.1035 -0.3511 1.0309 0.053 Uiso 1 1 calc R . . C14 C 0.1613(4) -0.5862(3) 0.96841(7) 0.0414(6) Uani 1 1 d . . . H14 H 0.0954 -0.6461 0.9887 0.050 Uiso 1 1 calc R . . C9 C 0.1617(4) -0.4981(3) 0.90193(7) 0.0360(6) Uani 1 1 d . . . C3 C -0.1789(4) -0.4176(3) 0.75287(7) 0.0406(6) Uani 1 1 d . . . H3 H -0.1010 -0.3614 0.7334 0.049 Uiso 1 1 calc R . . C4 C -0.0938(4) -0.4248(4) 0.78917(7) 0.0402(6) Uani 1 1 d . . . H4 H 0.0418 -0.3743 0.7942 0.048 Uiso 1 1 calc R . . C15 C 0.3662(5) -0.5028(3) 1.04257(7) 0.0367(6) Uani 1 1 d . . . C2 C -0.3810(4) -0.4937(3) 0.74502(7) 0.0371(6) Uani 1 1 d . . . C16 C 0.4738(4) -0.5936(3) 1.07117(7) 0.0413(6) Uani 1 1 d . . . H16 H 0.6025 -0.6546 1.0658 0.050 Uiso 1 1 calc R . . C17 C 0.3906(4) -0.5939(3) 1.10774(8) 0.0440(6) Uani 1 1 d . . . H17 H 0.4620 -0.6565 1.1270 0.053 Uiso 1 1 calc R . . C11 C 0.4566(4) -0.4100(3) 0.94346(7) 0.0374(6) Uani 1 1 d . . . H11 H 0.5883 -0.3506 0.9471 0.045 Uiso 1 1 calc R . . C13 C 0.0660(4) -0.5864(4) 0.93266(7) 0.0407(6) Uani 1 1 d . . . H13 H -0.0650 -0.6468 0.9291 0.049 Uiso 1 1 calc R . . N1 N 0.0764(4) -0.4859(3) 0.86435(6) 0.0417(5) Uani 1 1 d . . . C19 C 0.0924(5) -0.4111(4) 1.08708(7) 0.0458(7) Uani 1 1 d . . . H19 H -0.0363 -0.3501 1.0924 0.055 Uiso 1 1 calc R . . C8 C -0.1195(4) -0.5220(3) 0.85717(7) 0.0392(6) Uani 1 1 d . . . H8 H -0.2100 -0.5590 0.8770 0.047 Uiso 1 1 calc R . . C18 C 0.2015(5) -0.5014(3) 1.11576(7) 0.0410(6) Uani 1 1 d . . . O3 O 0.1124(4) -0.4980(3) 1.15177(6) 0.0589(6) Uani 1 1 d . . . C7 C -0.4997(4) -0.5727(3) 0.77399(8) 0.0434(6) Uani 1 1 d . . . H7 H -0.6353 -0.6231 0.7690 0.052 Uiso 1 1 calc R . . C6 C -0.4147(4) -0.5761(4) 0.81046(7) 0.0424(6) Uani 1 1 d . . . H6 H -0.4967 -0.6256 0.8302 0.051 Uiso 1 1 calc R . . C1 C -0.6495(5) -0.5653(6) 0.69756(9) 0.0723(10) Uani 1 1 d . . . H1A H -0.6414 -0.6910 0.7034 0.108 Uiso 1 1 calc R . . H1B H -0.6749 -0.5498 0.6707 0.108 Uiso 1 1 calc R . . H1C H -0.7668 -0.5119 0.7117 0.108 Uiso 1 1 calc R . . C12 C 0.3563(4) -0.4959(3) 0.97378(7) 0.0362(6) Uani 1 1 d . . . C5 C -0.2092(4) -0.5073(3) 0.81845(7) 0.0365(6) Uani 1 1 d . . . H1 H 0.196(8) -0.524(5) 1.1658(13) 0.091(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O2 0.0413(10) 0.0681(11) 0.0303(9) 0.0016(7) -0.0023(9) -0.0030(10) C10 0.0384(12) 0.0374(15) 0.0347(14) 0.0041(10) 0.0040(10) -0.0002(10) O1 0.0454(10) 0.0666(12) 0.0357(11) -0.0001(8) -0.0070(9) -0.0041(9) C20 0.0511(16) 0.0462(15) 0.0361(13) 0.0046(12) -0.0065(12) 0.0070(13) C14 0.0483(14) 0.0425(15) 0.0335(13) 0.0047(11) 0.0021(12) -0.0081(12) C9 0.0415(13) 0.0349(15) 0.0317(13) -0.0019(10) 0.0015(11) 0.0018(11) C3 0.0408(14) 0.0472(16) 0.0338(13) 0.0037(11) 0.0047(11) -0.0068(11) C4 0.0373(14) 0.0452(14) 0.0383(14) 0.0004(11) -0.0013(12) -0.0042(11) C15 0.0440(16) 0.0372(13) 0.0288(13) -0.0009(10) -0.0039(11) -0.0032(11) C2 0.0397(15) 0.0395(14) 0.0321(13) -0.0018(10) -0.0011(11) 0.0043(11) C16 0.0414(14) 0.0456(15) 0.0369(13) -0.0036(11) -0.0017(12) 0.0062(12) C17 0.0541(15) 0.0452(14) 0.0327(13) 0.0028(12) -0.0079(13) 0.0067(12) C11 0.0358(12) 0.0389(14) 0.0376(14) 0.0000(10) 0.0032(11) -0.0039(11) C13 0.0429(14) 0.0437(15) 0.0354(14) 0.0013(11) -0.0019(12) -0.0088(12) N1 0.0443(13) 0.0480(12) 0.0328(13) 0.0006(9) 0.0001(10) -0.0021(10) C19 0.0459(15) 0.0513(17) 0.0400(14) -0.0037(12) -0.0017(13) 0.0084(13) C8 0.0431(16) 0.0440(13) 0.0305(13) 0.0007(10) 0.0047(12) 0.0018(11) C18 0.0453(16) 0.0460(14) 0.0318(15) -0.0040(10) 0.0018(11) -0.0040(12) O3 0.0571(13) 0.0896(17) 0.0299(11) -0.0024(10) 0.0066(10) 0.0027(12) C7 0.0367(13) 0.0498(15) 0.0436(14) -0.0003(12) -0.0010(12) -0.0066(13) C6 0.0405(13) 0.0494(15) 0.0374(14) 0.0021(12) 0.0046(12) -0.0063(11) C1 0.0534(18) 0.115(3) 0.0485(19) -0.0068(19) -0.0116(15) -0.0188(19) C12 0.0429(13) 0.0356(13) 0.0302(14) -0.0030(10) -0.0021(11) 0.0032(10) C5 0.0392(15) 0.0371(14) 0.0332(13) -0.0004(10) 0.0011(11) 0.0051(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C12 1.379(3) . ? O2 C15 1.390(3) . ? C10 C11 1.378(3) . ? C10 C9 1.391(4) . ? C10 H10 0.9300 . ? O1 C2 1.371(3) . ? O1 C1 1.427(4) . ? C20 C15 1.377(4) . ? C20 C19 1.382(4) . ? C20 H20 0.9300 . ? C14 C13 1.381(3) . ? C14 C12 1.385(4) . ? C14 H14 0.9300 . ? C9 C13 1.390(4) . ? C9 N1 1.418(3) . ? C3 C4 1.374(3) . ? C3 C2 1.391(4) . ? C3 H3 0.9300 . ? C4 C5 1.389(4) . ? C4 H4 0.9300 . ? C15 C16 1.377(4) . ? C2 C7 1.380(4) . ? C16 C17 1.378(4) . ? C16 H16 0.9300 . ? C17 C18 1.379(4) . ? C17 H17 0.9300 . ? C11 C12 1.384(3) . ? C11 H11 0.9300 . ? C13 H13 0.9300 . ? N1 C8 1.257(3) . ? C19 C18 1.381(4) . ? C19 H19 0.9300 . ? C8 C5 1.466(3) . ? C8 H8 0.9300 . ? C18 O3 1.373(3) . ? O3 H1 0.74(4) . ? C7 C6 1.378(4) . ? C7 H7 0.9300 . ? C6 C5 1.390(4) . ? C6 H6 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O2 C15 120.79(19) . . ? C11 C10 C9 121.1(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C2 O1 C1 118.1(2) . . ? C15 C20 C19 120.1(2) . . ? C15 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C13 C14 C12 119.3(2) . . ? C13 C14 H14 120.4 . . ? C12 C14 H14 120.4 . . ? C13 C9 C10 118.1(2) . . ? C13 C9 N1 126.2(2) . . ? C10 C9 N1 115.6(2) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C16 C15 C20 120.3(3) . . ? C16 C15 O2 115.7(2) . . ? C20 C15 O2 123.7(2) . . ? O1 C2 C7 124.5(2) . . ? O1 C2 C3 115.5(2) . . ? C7 C2 C3 120.0(2) . . ? C15 C16 C17 119.8(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C18 120.0(2) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C10 C11 C12 119.7(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C14 C13 C9 121.4(2) . . ? C14 C13 H13 119.3 . . ? C9 C13 H13 119.3 . . ? C8 N1 C9 121.6(2) . . ? C18 C19 C20 119.5(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? N1 C8 C5 121.9(2) . . ? N1 C8 H8 119.1 . . ? C5 C8 H8 119.1 . . ? O3 C18 C17 122.1(2) . . ? O3 C18 C19 117.7(3) . . ? C17 C18 C19 120.2(3) . . ? C18 O3 H1 109(4) . . ? C6 C7 C2 119.2(2) . . ? C6 C7 H7 120.4 . . ? C2 C7 H7 120.4 . . ? C7 C6 C5 121.5(2) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C12 C11 115.2(2) . . ? O2 C12 C14 124.3(2) . . ? C11 C12 C14 120.3(2) . . ? C4 C5 C6 118.5(2) . . ? C4 C5 C8 121.5(2) . . ? C6 C5 C8 119.9(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.146 _refine_diff_density_min -0.110 _refine_diff_density_rms 0.028 # END# data_27 _database_code_depnum_ccdc_archive 'CCDC 265022' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'dicarboxylicdiphenyl ether ; _chemical_name_common "4,4'dicarboxylicdiphenyl ether" _chemical_melting_point 557 _chemical_formula_moiety 'C14 H10 O5' _chemical_formula_sum 'C14 H10 O5' _chemical_formula_weight 258.22 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 27.516(12) _cell_length_b 14.904(7) _cell_length_c 5.724(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2347.4(18) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 760 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 19.24 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; SADABSSiemens SADABS program multi-scan V2.03 R.H. Blessing, Acta Cryst. (1995) A51 33-38 ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15295 _diffrn_reflns_av_R_equivalents 0.2816 _diffrn_reflns_av_sigmaI/netI 0.1586 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2071 _reflns_number_gt 689 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2071 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2388 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O4 O 0.44257(12) 0.5905(2) 0.1100(6) 0.0650(11) Uani 1 1 d . . . O1 O 0.62937(12) 0.6090(2) 0.7708(5) 0.0638(11) Uani 1 1 d . . . O2 O 0.85420(14) 0.6009(2) 0.5748(6) 0.0706(11) Uani 1 1 d . . . O3 O 0.82995(13) 0.6763(2) 0.2590(7) 0.0782(12) Uani 1 1 d . . . C3 C 0.77030(17) 0.6331(3) 0.5333(9) 0.0420(14) Uani 1 1 d . . . O5 O 0.41671(14) 0.6705(2) 0.4161(6) 0.0744(11) Uani 1 1 d . . . C15 C 0.53602(18) 0.5764(3) 0.3195(8) 0.0479(14) Uani 1 1 d . . . H15 H 0.5315 0.5477 0.1769 0.058 Uiso 1 1 calc R . . C6 C 0.67490(16) 0.6170(3) 0.6757(9) 0.0445(13) Uani 1 1 d . . . C14 C 0.58138(17) 0.5720(3) 0.4272(9) 0.0500(14) Uani 1 1 d . . . H14 H 0.6068 0.5403 0.3593 0.060 Uiso 1 1 calc R . . C18 C 0.54933(17) 0.6613(3) 0.7410(8) 0.0503(14) Uani 1 1 d . . . H18 H 0.5538 0.6905 0.8830 0.060 Uiso 1 1 calc R . . C16 C 0.49764(17) 0.6223(3) 0.4190(9) 0.0419(13) Uani 1 1 d . . . C17 C 0.50460(17) 0.6629(3) 0.6321(9) 0.0483(14) Uani 1 1 d . . . H17 H 0.4787 0.6919 0.7042 0.058 Uiso 1 1 calc R . . C12 C 0.71190(17) 0.5851(3) 0.8151(8) 0.0460(14) Uani 1 1 d . . . H12 H 0.7046 0.5584 0.9577 0.055 Uiso 1 1 calc R . . C2 C 0.75937(17) 0.5925(3) 0.7446(9) 0.0506(14) Uani 1 1 d . . . H2 H 0.7842 0.5702 0.8385 0.061 Uiso 1 1 calc R . . C5 C 0.68532(16) 0.6584(3) 0.4673(9) 0.0495(14) Uani 1 1 d . . . H5 H 0.6605 0.6809 0.3741 0.059 Uiso 1 1 calc R . . C19 C 0.44962(18) 0.6264(3) 0.3051(10) 0.0482(15) Uani 1 1 d . . . C13 C 0.58746(17) 0.6159(3) 0.6373(9) 0.0463(14) Uani 1 1 d . . . C4 C 0.73321(17) 0.6659(3) 0.3981(8) 0.0445(13) Uani 1 1 d . . . H4 H 0.7405 0.6939 0.2570 0.053 Uiso 1 1 calc R . . C1 C 0.82105(19) 0.6379(3) 0.4498(11) 0.0531(16) Uani 1 1 d . . . H1A H 0.380(3) 0.671(3) 0.296(10) 0.15(2) Uiso 1 1 d . . . H2A H 0.893(3) 0.594(4) 0.491(11) 0.20(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O4 0.051(2) 0.084(3) 0.060(3) -0.016(2) -0.007(2) -0.001(2) O1 0.037(2) 0.106(3) 0.049(3) 0.015(2) 0.0001(19) -0.001(2) O2 0.043(2) 0.093(3) 0.076(3) 0.012(2) -0.002(2) 0.008(2) O3 0.047(3) 0.111(3) 0.077(3) 0.034(3) 0.005(2) 0.002(2) C3 0.036(3) 0.047(3) 0.043(4) -0.005(3) 0.003(3) -0.004(3) O5 0.044(2) 0.100(3) 0.080(3) -0.025(2) -0.008(2) 0.013(2) C15 0.055(3) 0.048(3) 0.041(4) -0.004(3) 0.004(3) -0.011(3) C6 0.038(3) 0.051(3) 0.044(4) -0.003(3) -0.005(3) 0.003(3) C14 0.038(3) 0.059(4) 0.053(4) -0.001(3) 0.007(3) 0.003(3) C18 0.046(3) 0.061(4) 0.045(4) 0.002(3) 0.007(3) -0.004(3) C16 0.038(3) 0.045(3) 0.043(4) 0.005(3) 0.008(3) 0.000(3) C17 0.042(3) 0.057(3) 0.045(4) 0.006(3) 0.008(3) 0.005(3) C12 0.049(3) 0.053(3) 0.037(3) 0.005(3) -0.001(3) 0.002(3) C2 0.045(4) 0.059(3) 0.047(4) 0.002(3) -0.009(3) 0.003(3) C5 0.041(3) 0.060(4) 0.047(4) 0.007(3) -0.004(3) 0.001(3) C19 0.038(4) 0.050(4) 0.057(4) 0.003(3) 0.004(3) 0.001(3) C13 0.037(3) 0.057(4) 0.045(4) 0.009(3) 0.001(3) 0.000(3) C4 0.051(3) 0.046(3) 0.037(3) 0.005(3) -0.003(3) -0.003(3) C1 0.053(4) 0.054(4) 0.052(4) 0.002(3) -0.009(4) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 C19 1.253(5) . ? O1 C6 1.371(5) . ? O1 C13 1.387(5) . ? O2 C1 1.284(5) . ? O2 H2A 1.17(8) . ? O3 C1 1.257(5) . ? C3 C4 1.371(5) . ? C3 C2 1.386(5) . ? C3 C1 1.478(6) . ? O5 C19 1.287(5) . ? O5 H1A 1.22(7) . ? C15 C16 1.381(5) . ? C15 C14 1.394(5) . ? C15 H15 0.9300 . ? C6 C5 1.373(5) . ? C6 C12 1.378(5) . ? C14 C13 1.379(5) . ? C14 H14 0.9300 . ? C18 C17 1.380(5) . ? C18 C13 1.382(5) . ? C18 H18 0.9300 . ? C16 C17 1.375(5) . ? C16 C19 1.475(6) . ? C17 H17 0.9300 . ? C12 C2 1.371(5) . ? C12 H12 0.9300 . ? C2 H2 0.9300 . ? C5 C4 1.381(5) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 C13 122.3(4) . . ? C1 O2 H2A 117(3) . . ? C4 C3 C2 119.2(5) . . ? C4 C3 C1 120.2(5) . . ? C2 C3 C1 120.6(5) . . ? C19 O5 H1A 108(3) . . ? C16 C15 C14 121.7(4) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? O1 C6 C5 125.1(5) . . ? O1 C6 C12 114.5(5) . . ? C5 C6 C12 120.2(4) . . ? C13 C14 C15 118.2(5) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C17 C18 C13 119.4(5) . . ? C17 C18 H18 120.3 . . ? C13 C18 H18 120.3 . . ? C17 C16 C15 118.5(5) . . ? C17 C16 C19 119.9(5) . . ? C15 C16 C19 121.5(5) . . ? C16 C17 C18 121.1(4) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C2 C12 C6 120.4(4) . . ? C2 C12 H12 119.8 . . ? C6 C12 H12 119.8 . . ? C12 C2 C3 119.9(5) . . ? C12 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C6 C5 C4 119.0(5) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? O4 C19 O5 123.3(5) . . ? O4 C19 C16 121.0(6) . . ? O5 C19 C16 115.6(6) . . ? C14 C13 C18 121.0(5) . . ? C14 C13 O1 123.1(5) . . ? C18 C13 O1 115.5(5) . . ? C3 C4 C5 121.3(5) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? O3 C1 O2 122.8(5) . . ? O3 C1 C3 119.1(5) . . ? O2 C1 C3 118.1(5) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.163 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.045 # END#