# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_q1 _database_code_depnum_ccdc_archive 'CCDC 917431' #TrackingRef 'AHNA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 N O3' _chemical_formula_weight 309.35 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 4.9619(4) _cell_length_b 13.1060(14) _cell_length_c 12.2014(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.684(6) _cell_angle_gamma 90.00 _cell_volume 793.12(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1457 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 22.79 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.6608 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 4293 _diffrn_reflns_av_R_equivalents 0.0164 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2456 _reflns_number_gt 1956 _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 '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^)+(0.0806P)^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 SHELXL _refine_ls_extinction_coef 0.015(5) _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 2.1(15) _refine_ls_number_reflns 2456 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1252 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.017 _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 0.3225(4) 1.01490(16) 1.05931(16) 0.0536(6) Uani 1 1 d . . . H1A H 0.4729 1.0154 1.0890 0.080 Uiso 1 1 calc R . . O2 O -0.4373(4) 0.74381(18) 0.64867(15) 0.0617(6) Uani 1 1 d . . . O3 O 0.2535(4) 0.57906(16) 0.82264(14) 0.0501(5) Uani 1 1 d . . . N1 N -0.0919(4) 0.66222(18) 0.73689(16) 0.0409(5) Uani 1 1 d . . . C1 C -0.2732(6) 1.0177(3) 0.8184(2) 0.0548(8) Uani 1 1 d . . . H1B H -0.3710 1.0769 0.8036 0.066 Uiso 1 1 calc R . . C2 C -0.3320(6) 0.9288(2) 0.7595(2) 0.0489(7) Uani 1 1 d . . . H2A H -0.4699 0.9291 0.7062 0.059 Uiso 1 1 calc R . . C3 C -0.1890(5) 0.8414(2) 0.7794(2) 0.0391(6) Uani 1 1 d . . . C4 C 0.0201(5) 0.8394(2) 0.86080(19) 0.0363(6) Uani 1 1 d . . . C5 C 0.0785(5) 0.9294(2) 0.9220(2) 0.0385(6) Uani 1 1 d . . . C6 C -0.0715(6) 1.0184(3) 0.8982(2) 0.0501(7) Uani 1 1 d . . . H6A H -0.0337 1.0782 0.9368 0.060 Uiso 1 1 calc R . . C7 C 0.2860(5) 0.9261(2) 1.0043(2) 0.0402(7) Uani 1 1 d G . . C8 C 0.4312(5) 0.8378(2) 1.02515(19) 0.0395(7) Uani 1 1 d G . . C9 C 0.3705(5) 0.7509(2) 0.96201(19) 0.0398(6) Uani 1 1 d . . . H9A H 0.4690 0.6916 0.9754 0.048 Uiso 1 1 calc R . . C10 C 0.1709(5) 0.7496(2) 0.88076(18) 0.0346(6) Uani 1 1 d . . . C11 C -0.2539(5) 0.7480(2) 0.71629(19) 0.0440(7) Uani 1 1 d . . . C12 C 0.1198(5) 0.6581(2) 0.81381(18) 0.0405(6) Uani 1 1 d . . . C15 C -0.1460(6) 0.5720(3) 0.6676(2) 0.0502(7) Uani 1 1 d . . . H15A H -0.3394 0.5631 0.6584 0.060 Uiso 1 1 calc R . . H15B H -0.0738 0.5119 0.7044 0.060 Uiso 1 1 calc R . . C16 C -0.0236(7) 0.5811(3) 0.5562(2) 0.0693(9) Uani 1 1 d . . . H16A H 0.1704 0.5734 0.5642 0.083 Uiso 1 1 calc R . . H16B H -0.0599 0.6488 0.5271 0.083 Uiso 1 1 calc R . . C17 C -0.1327(8) 0.5016(4) 0.4744(3) 0.0822(12) Uani 1 1 d . . . H17A H -0.3271 0.5089 0.4678 0.099 Uiso 1 1 calc R . . H17B H -0.0600 0.5160 0.4031 0.099 Uiso 1 1 calc R . . C18 C -0.0694(11) 0.3955(4) 0.5035(4) 0.1079(16) Uani 1 1 d . . . H18A H -0.1396 0.3509 0.4472 0.162 Uiso 1 1 calc R . . H18B H -0.1497 0.3790 0.5719 0.162 Uiso 1 1 calc R . . H18C H 0.1225 0.3873 0.5105 0.162 Uiso 1 1 calc R . . C20 C 0.6489(6) 0.8326(3) 1.1153(2) 0.0518(8) Uani 1 1 d . . . H20A H 0.7767 0.7797 1.0971 0.062 Uiso 1 1 calc R . . H20B H 0.7452 0.8970 1.1177 0.062 Uiso 1 1 calc R . . C21 C 0.5439(8) 0.8113(3) 1.2255(2) 0.0746(11) Uani 1 1 d . . . H21A H 0.3965 0.8499 1.2461 0.089 Uiso 1 1 calc R . . C22 C 0.6335(11) 0.7456(4) 1.2960(3) 0.1125(17) Uani 1 1 d . . . H22A H 0.7806 0.7049 1.2798 0.135 Uiso 1 1 calc R . . H22B H 0.5511 0.7388 1.3631 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 0.0503(11) 0.0413(13) 0.0687(12) -0.0144(10) -0.0092(9) 0.0031(10) O2 0.0575(12) 0.0642(16) 0.0620(11) -0.0036(11) -0.0243(9) 0.0007(12) O3 0.0585(11) 0.0317(11) 0.0595(11) -0.0040(9) -0.0100(8) 0.0088(10) N1 0.0443(12) 0.0374(13) 0.0405(10) -0.0043(10) -0.0051(8) -0.0010(11) C1 0.0560(17) 0.0431(19) 0.0653(17) 0.0086(15) -0.0018(13) 0.0147(15) C2 0.0459(15) 0.049(2) 0.0517(15) 0.0048(14) -0.0066(11) 0.0093(14) C3 0.0361(13) 0.0408(17) 0.0403(13) 0.0026(12) 0.0006(10) 0.0015(13) C4 0.0352(13) 0.0348(15) 0.0387(12) 0.0045(11) 0.0001(10) -0.0012(13) C5 0.0384(14) 0.0325(17) 0.0448(13) 0.0025(12) 0.0037(10) -0.0002(13) C6 0.0530(16) 0.0366(18) 0.0606(16) -0.0021(15) 0.0008(12) 0.0017(15) C7 0.0396(14) 0.0370(18) 0.0441(13) -0.0060(13) 0.0032(10) -0.0046(13) C8 0.0370(14) 0.0375(17) 0.0440(13) 0.0024(12) -0.0007(10) -0.0058(14) C9 0.0418(14) 0.0328(16) 0.0443(12) 0.0029(12) -0.0046(10) 0.0001(13) C10 0.0368(12) 0.0306(15) 0.0364(11) 0.0028(11) 0.0010(9) 0.0004(13) C11 0.0421(14) 0.0470(19) 0.0428(13) 0.0043(14) -0.0024(11) -0.0005(14) C12 0.0459(14) 0.0360(17) 0.0393(13) 0.0032(12) -0.0025(10) -0.0025(15) C15 0.0540(16) 0.0440(19) 0.0521(15) -0.0105(14) -0.0071(11) -0.0028(15) C16 0.084(2) 0.063(2) 0.0607(17) -0.0123(17) 0.0063(16) -0.006(2) C17 0.098(3) 0.085(3) 0.063(2) -0.022(2) -0.0052(17) 0.006(2) C18 0.150(5) 0.079(4) 0.095(3) -0.021(2) -0.003(3) 0.005(3) C20 0.0518(16) 0.046(2) 0.0570(16) -0.0027(14) -0.0148(12) -0.0041(15) C21 0.098(2) 0.073(3) 0.0519(16) -0.0036(18) -0.0193(15) 0.002(2) C22 0.149(4) 0.105(4) 0.082(3) 0.025(3) -0.035(3) -0.016(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 C7 1.353(3) . ? O1 H1A 0.8200 . ? O2 C11 1.212(3) . ? O3 C12 1.233(3) . ? N1 C12 1.389(3) . ? N1 C11 1.401(4) . ? N1 C15 1.473(4) . ? C1 C6 1.376(4) . ? C1 C2 1.396(5) . ? C1 H1B 0.9300 . ? C2 C3 1.366(4) . ? C2 H2A 0.9300 . ? C3 C4 1.415(3) . ? C3 C11 1.476(4) . ? C4 C10 1.412(4) . ? C4 C5 1.421(4) . ? C5 C6 1.410(4) . ? C5 C7 1.418(3) . ? C6 H6A 0.9300 . ? C7 C8 1.383(4) . ? C8 C9 1.402(4) . ? C8 C20 1.520(3) . ? C9 C10 1.381(3) . ? C9 H9A 0.9300 . ? C10 C12 1.468(4) . ? C15 C16 1.510(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.531(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.467(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C20 C21 1.483(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.287(6) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C22 H22B 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 O1 H1A 109.5 . . ? C12 N1 C11 124.8(2) . . ? C12 N1 C15 118.6(2) . . ? C11 N1 C15 116.6(2) . . ? C6 C1 C2 120.4(3) . . ? C6 C1 H1B 119.8 . . ? C2 C1 H1B 119.8 . . ? C3 C2 C1 120.6(2) . . ? C3 C2 H2A 119.7 . . ? C1 C2 H2A 119.7 . . ? C2 C3 C4 120.4(2) . . ? C2 C3 C11 119.9(2) . . ? C4 C3 C11 119.7(2) . . ? C3 C4 C10 120.7(2) . . ? C3 C4 C5 119.2(2) . . ? C10 C4 C5 120.2(2) . . ? C6 C5 C4 118.7(2) . . ? C6 C5 C7 122.6(2) . . ? C4 C5 C7 118.7(2) . . ? C1 C6 C5 120.6(3) . . ? C1 C6 H6A 119.7 . . ? C5 C6 H6A 119.7 . . ? O1 C7 C8 124.6(2) . . ? O1 C7 C5 114.2(2) . . ? C8 C7 C5 121.2(2) . . ? C7 C8 C9 118.4(2) . . ? C7 C8 C20 121.7(2) . . ? C9 C8 C20 119.9(3) . . ? C10 C9 C8 122.9(3) . . ? C10 C9 H9A 118.6 . . ? C8 C9 H9A 118.6 . . ? C9 C10 C4 118.6(2) . . ? C9 C10 C12 121.2(2) . . ? C4 C10 C12 120.2(2) . . ? O2 C11 N1 120.1(3) . . ? O2 C11 C3 122.8(3) . . ? N1 C11 C3 117.2(2) . . ? O3 C12 N1 119.1(2) . . ? O3 C12 C10 123.6(2) . . ? N1 C12 C10 117.3(2) . . ? N1 C15 C16 112.5(3) . . ? N1 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? N1 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C15 C16 C17 112.9(3) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C16 114.7(3) . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C20 C8 113.8(2) . . ? C21 C20 H20A 108.8 . . ? C8 C20 H20A 108.8 . . ? C21 C20 H20B 108.8 . . ? C8 C20 H20B 108.8 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 127.5(4) . . ? C22 C21 H21A 116.3 . . ? C20 C21 H21A 116.3 . . ? C21 C22 H22A 120.0 . . ? C21 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.155 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.036 data_q1a _database_code_depnum_ccdc_archive 'CCDC 917432' #TrackingRef 'Hg-AHNA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 Cl Hg N O3' _chemical_formula_weight 544.38 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(2)/mbc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-y, x, z+1/2' 'y, -x, z+1/2' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 'y+1/2, x+1/2, -z+1/2' '-y+1/2, -x+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z' 'y, -x, -z-1/2' '-y, x, -z-1/2' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' '-y-1/2, -x-1/2, z-1/2' 'y-1/2, x-1/2, z-1/2' _cell_length_a 23.616(3) _cell_length_b 23.616(3) _cell_length_c 6.9313(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3865.6(10) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2222 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 18.13 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.871 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_absorpt_coefficient_mu 8.118 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.5135 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 20463 _diffrn_reflns_av_R_equivalents 0.0742 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1863 _reflns_number_gt 1192 _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 '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^)+(0.0383P)^2^+9.6000P] 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 1863 _refine_ls_number_parameters 140 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0825 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _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 Hg1 Hg 0.09300(2) 1.007858(19) 0.0000 0.0867(3) Uani 1 2 d S . . Cl1 Cl 0.02262(15) 1.07674(13) 0.0000 0.0964(12) Uani 1 2 d S . . O1 O 0.2187(3) 0.8758(4) 0.0000 0.126(4) Uani 1 2 d S . . O2 O 0.2977(5) 0.5822(4) 0.0000 0.179(6) Uani 1 2 d S . . O3 O 0.1130(5) 0.6334(4) 0.0000 0.138(5) Uani 1 2 d S . . N1 N 0.2063(6) 0.6072(5) 0.0000 0.134(5) Uani 1 2 d S . . C1 C 0.1630(8) 0.9541(8) 0.0000 0.134(6) Uiso 1 2 d S . . C2' C 0.1616(7) 0.9066(7) -0.084(2) 0.078(5) Uiso 0.50 1 d P . . C3 C 0.1149(6) 0.8590(5) 0.0000 0.128(7) Uani 1 2 d S . . C4 C 0.1532(6) 0.8057(5) 0.0000 0.101(5) Uani 1 2 d S . . C5 C 0.2076(6) 0.8194(6) 0.0000 0.101(5) Uani 1 2 d S . . C6 C 0.2523(5) 0.7794(6) 0.0000 0.091(4) Uani 1 2 d S . . C7 C 0.2360(6) 0.7225(6) 0.0000 0.086(4) Uani 1 2 d S . . C8 C 0.1795(6) 0.7079(5) 0.0000 0.097(5) Uani 1 2 d S . . C9 C 0.1373(6) 0.7488(6) 0.0000 0.098(5) Uani 1 2 d S . . H9A H 0.0993 0.7386 0.0000 0.118 Uiso 1 2 calc SR . . C10 C 0.3094(6) 0.7932(6) 0.0000 0.105(5) Uani 1 2 d S . . H10A H 0.3206 0.8309 0.0000 0.126 Uiso 1 2 calc SR . . C11 C 0.3500(7) 0.7504(8) 0.0000 0.123(6) Uani 1 2 d S . . H11A H 0.3883 0.7594 0.0000 0.148 Uiso 1 2 calc SR . . C12 C 0.3329(7) 0.6944(7) 0.0000 0.118(6) Uani 1 2 d S . . H12A H 0.3599 0.6657 0.0000 0.142 Uiso 1 2 calc SR . . C13 C 0.2786(7) 0.6813(6) 0.0000 0.111(5) Uani 1 2 d S . . C14 C 0.2629(9) 0.6211(7) 0.0000 0.143(7) Uani 1 2 d S . . C15 C 0.1622(7) 0.6482(6) 0.0000 0.115(6) Uani 1 2 d S . . C16 C 0.1880(10) 0.5432(9) 0.0000 0.198(14) Uani 1 2 d S . . C17 C 0.1764(15) 0.5231(15) 0.147(6) 0.160(12) Uiso 0.50 1 d P . . C18 C 0.1459(17) 0.4623(18) 0.074(8) 0.26(2) Uiso 0.50 1 d PD . . C19 C 0.131(3) 0.458(3) 0.299(10) 0.49(4) Uiso 0.50 1 d PD . . 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 Hg1 0.0730(4) 0.0540(3) 0.1331(6) 0.000 0.000 0.0048(2) Cl1 0.081(2) 0.0650(19) 0.143(3) 0.000 0.000 0.0118(16) O1 0.069(6) 0.061(6) 0.247(14) 0.000 0.000 0.013(4) O2 0.142(10) 0.076(7) 0.32(2) 0.000 0.000 0.050(7) O3 0.114(8) 0.065(6) 0.235(15) 0.000 0.000 0.004(6) N1 0.117(11) 0.058(7) 0.227(17) 0.000 0.000 0.019(7) C3 0.076(8) 0.045(7) 0.26(2) 0.000 0.000 0.006(6) C4 0.073(9) 0.058(8) 0.173(16) 0.000 0.000 0.006(7) C5 0.082(10) 0.064(8) 0.158(15) 0.000 0.000 0.012(8) C6 0.061(8) 0.074(8) 0.139(14) 0.000 0.000 0.007(7) C7 0.075(9) 0.076(9) 0.106(12) 0.000 0.000 0.013(7) C8 0.097(10) 0.059(8) 0.134(15) 0.000 0.000 0.013(7) C9 0.077(8) 0.068(8) 0.151(14) 0.000 0.000 0.004(7) C10 0.078(9) 0.092(10) 0.146(16) 0.000 0.000 0.017(8) C11 0.085(10) 0.116(13) 0.168(17) 0.000 0.000 0.039(10) C12 0.090(11) 0.087(11) 0.178(18) 0.000 0.000 0.034(9) C13 0.099(12) 0.073(9) 0.160(16) 0.000 0.000 0.025(9) C14 0.124(15) 0.080(11) 0.23(2) 0.000 0.000 0.040(11) C15 0.099(11) 0.066(9) 0.180(18) 0.000 0.000 0.013(9) C16 0.137(19) 0.091(15) 0.36(5) 0.000 0.000 0.011(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 Hg1 C1 2.083(19) . ? Hg1 Cl1 2.326(3) . ? O1 C5 1.356(14) . ? O1 C2' 1.639(18) . ? O1 C2' 1.639(18) 10 ? O2 C14 1.234(17) . ? O3 C15 1.214(16) . ? N1 C14 1.38(2) . ? N1 C15 1.422(17) . ? N1 C16 1.57(2) . ? C1 C2' 1.265(19) . ? C1 C2' 1.265(19) 10 ? C2' C2' 1.16(3) 10 ? C2' C3 1.676(19) . ? C3 C4 1.551(16) . ? C3 C2' 1.676(19) 10 ? C4 C5 1.325(17) . ? C4 C9 1.394(17) . ? C5 C6 1.417(16) . ? C6 C10 1.387(16) . ? C6 C7 1.397(18) . ? C7 C8 1.377(18) . ? C7 C13 1.400(17) . ? C8 C9 1.389(17) . ? C8 C15 1.468(18) . ? C9 H9A 0.9300 . ? C10 C11 1.392(18) . ? C10 H10A 0.9300 . ? C11 C12 1.38(2) . ? C11 H11A 0.9300 . ? C12 C13 1.320(19) . ? C12 H12A 0.9300 . ? C13 C14 1.47(2) . ? C16 C17 1.15(3) 10 ? C16 C17 1.15(3) . ? C17 C18 1.68(5) . ? C17 C17 2.03(8) 10 ? C18 C18 1.03(11) 10 ? C18 C19 1.60(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 C1 Hg1 Cl1 173.1(5) . . ? C5 O1 C2' 106.1(9) . . ? C5 O1 C2' 106.1(9) . 10 ? C2' O1 C2' 41.5(12) . 10 ? C14 N1 C15 123.1(13) . . ? C14 N1 C16 119.8(14) . . ? C15 N1 C16 117.0(15) . . ? C2' C1 C2' 54.7(17) . 10 ? C2' C1 Hg1 121.3(14) . . ? C2' C1 Hg1 121.3(14) 10 . ? C2' C2' C1 62.7(8) 10 . ? C2' C2' O1 69.2(6) 10 . ? C1 C2' O1 102.1(14) . . ? C2' C2' C3 69.7(6) 10 . ? C1 C2' C3 116.9(14) . . ? O1 C2' C3 96.9(10) . . ? C4 C3 C2' 99.3(10) . 10 ? C4 C3 C2' 99.3(10) . . ? C2' C3 C2' 40.6(12) 10 . ? C5 C4 C9 119.8(12) . . ? C5 C4 C3 111.5(12) . . ? C9 C4 C3 128.7(12) . . ? C4 C5 O1 115.3(12) . . ? C4 C5 C6 124.0(13) . . ? O1 C5 C6 120.7(12) . . ? C10 C6 C7 119.7(12) . . ? C10 C6 C5 124.6(13) . . ? C7 C6 C5 115.7(12) . . ? C8 C7 C6 120.6(12) . . ? C8 C7 C13 121.5(13) . . ? C6 C7 C13 118.0(13) . . ? C7 C8 C9 121.4(12) . . ? C7 C8 C15 120.6(13) . . ? C9 C8 C15 118.0(13) . . ? C8 C9 C4 118.5(13) . . ? C8 C9 H9A 120.8 . . ? C4 C9 H9A 120.8 . . ? C6 C10 C11 119.9(14) . . ? C6 C10 H10A 120.0 . . ? C11 C10 H10A 120.0 . . ? C12 C11 C10 119.6(15) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C13 C12 C11 120.4(14) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C7 122.5(14) . . ? C12 C13 C14 118.1(15) . . ? C7 C13 C14 119.4(15) . . ? O2 C14 N1 118.0(17) . . ? O2 C14 C13 123.5(18) . . ? N1 C14 C13 118.5(14) . . ? O3 C15 N1 120.2(14) . . ? O3 C15 C8 122.9(14) . . ? N1 C15 C8 116.9(14) . . ? C17 C16 C17 123(5) 10 . ? C17 C16 N1 117(3) 10 . ? C17 C16 N1 117(3) . . ? C16 C17 C18 101(4) . . ? C16 C17 C17 28(3) . 10 ? C18 C17 C17 73(2) . 10 ? C18 C18 C19 167(3) 10 . ? C18 C18 C17 107(2) 10 . ? C19 C18 C17 82(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.868 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.094