# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2005 data_global _audit_creation_method maXus _journal_coden_Cambridge 440 loop_ _publ_author_name 'M. Hosseini' 'Sylvie Ferlay' 'Abdelaziz Jouaiti' 'Nathalie Kyritsakas' 'Jerome Pansanel' 'Jean-Marc Planeix' _publ_contact_author_name 'M. Hosseini' _publ_contact_author_address ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur 4 rue Blaise Pascal 67000 Strasbourg ; _publ_contact_author_email HOSSEINI@CHIMIE.U-STRASBG.FR _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Molecular tectonics: generation of 2-D molecular networks by combination of coordination and hydrogen bonds ; _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. Sheldrick, G.M. (1997). SHELXS-97. Program for Crystal Structure Solution. University of Gottingen, Germany. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of Gottingen, Germany. Maslen, E.N. (1992) In International Tables for Crystallography Volme C edited by A.J.C.Wilson pp 521-525. Cpenhagem: Munksgaard. ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 284053' _chemical_compound_source 'Local laboratory' _exptl_crystal_description plate _exptl_crystal_colour Colourless _cell_measurement_temperature 173 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _refine_ls_hydrogen_treatment mixed # Submission details _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 2.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_special_details ; ? ; _chemical_formula_weight 589.832 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _symmetry_space_group_name_H-M 'P 2/c ' _symmetry_cell_setting Monoclinic _chemical_formula_moiety 'C18 H14 Cl2 Hg N4 O2 ' _chemical_formula_sum 'C18 H14 Cl2 Hg N4 O2 ' _chemical_name_systematic ; ? ; _cell_length_a 13.0454(5) _cell_length_b 5.0255(10) _cell_length_c 13.777(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.005(9) _cell_angle_gamma 90.00 _cell_volume 898.2(2) _diffrn_reflns_number 16713 _diffrn_reflns_theta_max 32.99 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_full 32.99 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _diffrn_measurement_method CCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.051 _exptl_absorpt_correction_T_max 0.158 _exptl_absorpt_process_details ; Sphere (Maslen, 1992) ; 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' 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' 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' _exptl_absorpt_coefficient_mu 8.888 _reflns_number_total 3354 _reflns_number_gt 2557 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0513P)^2^+0.8752P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3354 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 Hg1 Hg 0.5000 -0.00379(4) 0.2500 0.02617(7) Uani 1 2 d S . . N1 N 0.3710(2) 0.3202(6) 0.1847(2) 0.0263(6) Uani 1 1 d . . . C5 C 0.3764(3) 0.4553(8) 0.1017(3) 0.0290(8) Uani 1 1 d . . . C1 C 0.2970(3) 0.3840(7) 0.2413(2) 0.0226(6) Uani 1 1 d . . . C2 C 0.2267(3) 0.5893(7) 0.2187(2) 0.0221(6) Uani 1 1 d . . . C3 C 0.2347(3) 0.7307(8) 0.1333(3) 0.0277(7) Uani 1 1 d . . . C6 C 0.1517(2) 0.6673(6) 0.2878(2) 0.0214(6) Uani 1 1 d . . . C4 C 0.3094(3) 0.6608(8) 0.0736(3) 0.0315(8) Uani 1 1 d . . . Cl1 Cl 0.58545(7) -0.1154(2) 0.11315(7) 0.03204(19) Uani 1 1 d . . . N2 N 0.1162(3) 0.4652(5) 0.3398(2) 0.0237(6) Uani 1 1 d . . . O1 O 0.1272(2) 0.9020(6) 0.2967(2) 0.0303(5) Uani 1 1 d . . . C7 C 0.0563(3) 0.4904(6) 0.4193(3) 0.0209(6) Uani 1 1 d . . . C9 C -0.0174(3) 0.2969(7) 0.4321(3) 0.0247(6) Uani 1 1 d . . . C8 C 0.0733(3) 0.6953(7) 0.4879(3) 0.0258(6) Uani 1 1 d . . . H5 H 0.4278 0.4082 0.0608 0.035 Uiso 1 1 d R . . H1 H 0.2922 0.2844 0.2993 0.027 Uiso 1 1 d R . . H3 H 0.1893 0.8748 0.1158 0.033 Uiso 1 1 d R . . H4 H 0.3146 0.7530 0.0141 0.038 Uiso 1 1 d R . . H2 H 0.1321 0.3027 0.3228 0.028 Uiso 1 1 d R . . H9 H -0.0296 0.1583 0.3854 0.030 Uiso 1 1 d R . . H8 H 0.1231 0.8289 0.4796 0.031 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 Hg1 0.02131(9) 0.02735(11) 0.03105(10) 0.000 0.00847(6) 0.000 N1 0.0245(13) 0.0268(14) 0.0290(14) -0.0013(11) 0.0091(11) -0.0005(11) C5 0.0294(17) 0.0294(19) 0.0304(16) -0.0023(13) 0.0130(14) -0.0018(13) C1 0.0218(14) 0.0220(16) 0.0250(14) 0.0010(12) 0.0072(11) 0.0031(12) C2 0.0221(14) 0.0187(13) 0.0257(14) -0.0008(12) 0.0040(11) 0.0001(13) C3 0.0276(16) 0.0280(17) 0.0285(16) 0.0035(13) 0.0085(13) 0.0015(13) C6 0.0216(14) 0.0176(13) 0.0259(14) -0.0005(11) 0.0067(11) 0.0010(11) C4 0.0314(18) 0.038(2) 0.0267(15) 0.0058(14) 0.0085(14) -0.0021(15) Cl1 0.0300(4) 0.0376(5) 0.0297(4) -0.0038(4) 0.0086(3) -0.0002(4) N2 0.0256(14) 0.0185(13) 0.0288(13) 0.0004(10) 0.0111(11) 0.0034(10) O1 0.0356(14) 0.0172(11) 0.0405(14) 0.0007(11) 0.0156(11) 0.0032(11) C7 0.0216(13) 0.0168(13) 0.0255(13) 0.0030(11) 0.0086(11) 0.0021(11) C9 0.0279(16) 0.0179(14) 0.0296(15) -0.0038(12) 0.0091(13) -0.0014(12) C8 0.0285(16) 0.0217(15) 0.0286(15) -0.0021(12) 0.0101(13) -0.0026(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 Cl1 2.3562(9) 2_655 ? Hg1 Cl1 2.3563(9) . ? Hg1 N1 2.444(3) 2_655 ? Hg1 N1 2.444(3) . ? N1 C5 1.338(5) . ? N1 C1 1.342(4) . ? C5 C4 1.381(6) . ? C1 C2 1.394(5) . ? C2 C3 1.388(5) . ? C2 C6 1.487(4) . ? C3 C4 1.385(5) . ? C6 O1 1.231(4) . ? C6 N2 1.352(4) . ? N2 C7 1.416(5) . ? C7 C9 1.391(5) . ? C7 C8 1.400(5) . ? C9 C8 1.384(4) 3_566 ? C8 C9 1.384(4) 3_566 ? C5 H5 0.9500 . ? C1 H1 0.9500 . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? N2 H2 0.8800 . ? C9 H9 0.9500 . ? C8 H8 0.9499 . ? 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 Cl1 Hg1 Cl1 152.45(5) 2_655 . ? Cl1 Hg1 N1 103.24(7) 2_655 2_655 ? Cl1 Hg1 N1 95.06(7) . 2_655 ? Cl1 Hg1 N1 95.06(7) 2_655 . ? Cl1 Hg1 N1 103.24(7) . . ? N1 Hg1 N1 96.48(15) 2_655 . ? C5 N1 C1 118.7(3) . . ? C5 N1 Hg1 123.8(2) . . ? C1 N1 Hg1 117.0(2) . . ? N1 C5 C4 122.0(3) . . ? N1 C1 C2 122.9(3) . . ? C3 C2 C1 117.5(3) . . ? C3 C2 C6 121.4(3) . . ? C1 C2 C6 120.9(3) . . ? C4 C3 C2 119.6(3) . . ? O1 C6 N2 124.0(3) . . ? O1 C6 C2 120.7(3) . . ? N2 C6 C2 115.2(3) . . ? C5 C4 C3 119.2(3) . . ? C6 N2 C7 126.2(3) . . ? C9 C7 C8 119.4(3) . . ? C9 C7 N2 118.7(3) . . ? C8 C7 N2 121.8(3) . . ? C8 C9 C7 120.6(3) 3_566 . ? C9 C8 C7 119.9(3) 3_566 . ? N1 C5 H5 118.9 . . ? C4 C5 H5 119.1 . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.6 . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.3 . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 N2 H2 116.9 . . ? C7 N2 H2 116.9 . . ? C8 C9 H9 119.7 3_566 . ? C7 C9 H9 119.7 . . ? C9 C8 H8 120.0 3_566 . ? C7 C8 H8 120.0 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 3.330 _refine_diff_density_min -2.869 _refine_diff_density_rms 0.208 #=============================================================================== data_st1286 _database_code_depnum_ccdc_archive 'CCDC 284054' #=============================================================================== _audit_creation_date 19-11-02 _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158-166. ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C18 H14 Cl2 Hg N4 O2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H14 Cl2 Hg N4 O2' _chemical_formula_weight 589.83 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Cl ? 0.132 0.159 International_Tables_Vol_IV_Table_2.3.1 Hg ? -3.084 9.223 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 8.3336(2) _cell_length_b 9.2373(2) _cell_length_c 11.4459(3) _cell_angle_alpha 90 _cell_angle_beta 94.207(5) _cell_angle_gamma 90 _cell_volume 878.73(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 4717 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 30.0 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.23 _exptl_crystal_density_method none _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 9.085 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.9653 _exptl_absorpt_correction_T_max 1.1138 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 4717 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 36. mm. Scan angle = 2.0 deg 1 scans of 30 sec per frame. Data collection was divided into 2 set(s) with the following starting angles and number of frames : Set 1 Theta = 8.80 Omega = 0.00 Kappa = 0.00 90 frames Set 2 Theta = -8.50 Kappa = -172.00 Phi = 0.00 16 frames Friedel pairs were averaged. Internal R = 0.04 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4717 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2722 _reflns_number_gt 1928 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1928 _refine_ls_number_parameters 124 _refine_ls_number_restraints 7 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.026 _refine_ls_R_factor_gt 0.017 _refine_ls_wR_factor_all 0.036 _refine_ls_wR_factor_ref 0.022 _refine_ls_goodness_of_fit_all 1.507 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_shift/su_max 0.003 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.944 _refine_diff_density_min -1.782 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol HG 0.0000 0.0000 1.0000 0.0170 0.500 Uani ? ? Hg CL 0.03522(7) -0.25026(6) 1.04430(5) 0.0245(2) 1.000 Uani ? ? Cl N1 0.2670(3) 0.0052(1) 0.8927(2) 0.020(1) 1.000 Uani ? ? N C1 0.3648(3) -0.1102(2) 0.9039(2) 0.024(1) 1.000 Uani ? ? C C2 0.5128(3) -0.1158(2) 0.8589(2) 0.023(1) 1.000 Uani ? ? C C3 0.5646(4) 0.0011(2) 0.7957(3) 0.016(1) 1.000 Uani ? ? C C4 0.4647(3) 0.1219(2) 0.7836(2) 0.020(1) 1.000 Uani ? ? C C5 0.3194(3) 0.1197(2) 0.8339(2) 0.022(1) 1.000 Uani ? ? C C6 0.7259(4) -0.0147(2) 0.7472(2) 0.017(1) 1.000 Uani ? ? C O 0.8323(2) -0.0841(1) 0.8008(1) 0.0223(8) 1.000 Uani ? ? O N2 0.7428(2) 0.0478(2) 0.6412(2) 0.0168(8) 1.000 Uani ? ? N C7 0.8741(3) 0.0228(2) 0.5718(2) 0.016(1) 1.000 Uani ? ? C C8 1.0303(4) 0.0025(2) 0.6212(3) 0.019(1) 1.000 Uani ? ? C C9 0.8445(3) 0.0197(2) 0.4510(2) 0.019(1) 1.000 Uani ? ? C H01 0.6417 0.0850 0.5923 0.0225 1.000 Uiso ? ? H H1 0.3297 -0.1923 0.9451 0.0303 1.000 Uiso calc C1 H H2 0.5791 -0.1989 0.8709 0.0300 1.000 Uiso calc C2 H H3 0.4962 0.2045 0.7415 0.0264 1.000 Uiso calc C4 H H4 0.2530 0.2033 0.8267 0.0288 1.000 Uiso calc C5 H H5 1.0514 0.0038 0.7039 0.0257 1.000 Uiso calc C8 H H6 0.7380 0.0329 0.4173 0.0257 1.000 Uiso calc C9 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol HG 0.0165 0.01632(6) 0.01835(6) 0.00182(4) 0.00314(6) 0.00200(4) Hg CL 0.0215(3) 0.0203(2) 0.0335(2) 0.0028(2) 0.0074(2) 0.0075(3) Cl N1 0.016(1) 0.021(1) 0.024(1) 0.0011(6) 0.004(1) -0.0002(6) N C1 0.025(1) 0.020(1) 0.026(1) 0.0013(9) 0.009(1) 0.0044(9) C C2 0.023(1) 0.019(1) 0.027(1) 0.0036(9) 0.008(1) 0.0049(9) C C3 0.014(1) 0.020(1) 0.016(1) 0.0010(7) 0.002(1) -0.0023(7) C C4 0.020(1) 0.020(1) 0.021(1) 0.0016(9) 0.004(1) 0.0035(9) C C5 0.021(1) 0.021(1) 0.024(1) 0.0026(9) 0.005(1) 0.0005(9) C C6 0.015(1) 0.017(1) 0.018(1) -0.0017(8) 0.005(1) -0.0035(7) C O 0.0198(8) 0.0269(7) 0.0208(8) 0.0067(7) 0.0022(7) 0.0025(6) O N2 0.0129(9) 0.0203(7) 0.0181(9) 0.0029(8) 0.0027(8) 0.0031(8) N C7 0.015(1) 0.0128(8) 0.021(1) -0.0005(8) 0.003(1) -0.0001(8) C C8 0.013(1) 0.029(1) 0.018(1) -0.0014(8) 0.001(1) 0.0003(7) C C9 0.014(1) 0.027(1) 0.019(1) 0.0014(9) 0.000(1) 0.0016(8) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag HG CL 2.3802 . . ? HG N1 2.6197 . . ? HG O 2.6997 . ._455 ? N1 C1 1.342(3) . . ? N1 C5 1.344(3) . . ? C1 C2 1.372(4) . . ? C2 C3 1.386(3) . . ? C3 C4 1.393(3) . . ? C3 C6 1.499(4) . . ? C4 C5 1.379(3) . . ? C6 O 1.222(3) . . ? C6 N2 1.360(3) . . ? N2 C7 1.417(3) . . ? N2 H01 1.0356 . . ? C7 C8 1.394(4) . . ? C7 C9 1.386(4) . . ? C8 C9 1.393(4) . 3_756 ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag CL HG N1 91.25 . . . ? CL HG O 87.05 . . ._455 ? N1 HG O 90.81 . . ._455 ? C1 N1 C5 117.1(3) . . . ? N1 C1 C2 123.4(2) . . . ? C1 C2 C3 119.3(2) . . . ? C2 C3 C4 118.0(3) . . . ? C2 C3 C6 116.1(2) . . . ? C4 C3 C6 125.9(2) . . . ? C3 C4 C5 118.9(2) . . . ? N1 C5 C4 123.3(2) . . . ? C3 C6 O 120.2(3) . . . ? C3 C6 N2 116.3(3) . . . ? O C6 N2 123.5(3) . . . ? C6 N2 C7 124.4(2) . . . ? C6 N2 H01 119.37 . . . ? C7 N2 H01 112.42 . . . ? N2 C7 C8 122.1(3) . . . ? N2 C7 C9 118.3(3) . . . ? C8 C7 C9 119.6(3) . . . ? C7 C8 C9 119.8(3) . . 3_756 ? C7 C9 C8 120.6(3) . . 3_756 ?