# Electronic Supplementary Material (ESI) for CrystEngComm # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 Br2 Cd N5' _chemical_formula_weight 611.62 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 '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 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 14.7153(13) _cell_length_b 9.0139(8) _cell_length_c 16.3787(14) _cell_angle_alpha 90.00 _cell_angle_beta 107.313(3) _cell_angle_gamma 90.00 _cell_volume 2074.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 4.924 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.301 _exptl_absorpt_correction_T_max 0.478 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27686 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.49 _reflns_number_total 5126 _reflns_number_gt 3637 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1000P)^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 5126 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 0.815 _refine_ls_restrained_S_all 0.815 _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 Cd1 Cd 0.26452(2) 0.05011(4) 0.12935(2) 0.03090(12) Uani 1 1 d . . . Br1 Br 0.37602(4) -0.07003(6) 0.25956(3) 0.04628(16) Uani 1 1 d . . . Br2 Br 0.29660(4) -0.00710(6) -0.01149(3) 0.04359(16) Uani 1 1 d . . . N1 N 0.3162(3) 0.2966(4) 0.1450(2) 0.0315(8) Uani 1 1 d . . . C1 C 0.3524(3) 0.3589(5) 0.2219(3) 0.0310(10) Uani 1 1 d . . . H1 H 0.3504 0.3068 0.2704 0.037 Uiso 1 1 calc R . . C2 C 0.3932(3) 0.5007(5) 0.2313(3) 0.0280(9) Uani 1 1 d . . . C3 C 0.3957(3) 0.5763(5) 0.1580(3) 0.0310(10) Uani 1 1 d . . . H3 H 0.4209 0.6716 0.1625 0.037 Uiso 1 1 calc R . . C4 C 0.3611(3) 0.5109(5) 0.0786(3) 0.0286(9) Uani 1 1 d . . . C5 C 0.3212(3) 0.3696(5) 0.0757(3) 0.0306(9) Uani 1 1 d . . . H5 H 0.2969 0.3241 0.0227 0.037 Uiso 1 1 calc R . . N11 N 0.3004(3) 0.5450(4) -0.0762(2) 0.0354(9) Uani 1 1 d . . . N12 N 0.4317(3) 0.6763(4) -0.0109(2) 0.0329(8) Uani 1 1 d . . . C11 C 0.3631(3) 0.5782(5) -0.0031(3) 0.0313(10) Uani 1 1 d . . . C12 C 0.3268(3) 0.6295(5) -0.1366(3) 0.0334(10) Uani 1 1 d . . . C13 C 0.4078(3) 0.7120(5) -0.0968(3) 0.0341(10) Uani 1 1 d . . . C14 C 0.4481(4) 0.8093(6) -0.1418(3) 0.0454(12) Uani 1 1 d . . . H14 H 0.5023 0.8640 -0.1147 0.054 Uiso 1 1 calc R . . C15 C 0.4038(4) 0.8211(7) -0.2290(3) 0.0524(14) Uani 1 1 d . . . H15 H 0.4286 0.8854 -0.2613 0.063 Uiso 1 1 calc R . . C16 C 0.3230(4) 0.7386(7) -0.2691(3) 0.0559(15) Uani 1 1 d . . . H16 H 0.2947 0.7498 -0.3276 0.067 Uiso 1 1 calc R . . C17 C 0.2840(4) 0.6414(6) -0.2248(3) 0.0455(12) Uani 1 1 d . . . H17 H 0.2307 0.5852 -0.2525 0.055 Uiso 1 1 calc R . . C18 C 0.5136(4) 0.7376(6) 0.0539(3) 0.0442(12) Uani 1 1 d . . . H18A H 0.5475 0.8036 0.0272 0.066 Uiso 1 1 calc R . . H18B H 0.5550 0.6584 0.0816 0.066 Uiso 1 1 calc R . . H18C H 0.4924 0.7912 0.0954 0.066 Uiso 1 1 calc R . . N21 N 0.3867(3) 0.5779(4) 0.3758(2) 0.0279(8) Uani 1 1 d . . . N22 N 0.5177(2) 0.6345(4) 0.3425(2) 0.0307(8) Uani 1 1 d . . . C21 C 0.4311(3) 0.5670(5) 0.3158(3) 0.0288(9) Uani 1 1 d . . . C22 C 0.4461(3) 0.6586(5) 0.4424(3) 0.0293(9) Uani 1 1 d . . . C23 C 0.5285(3) 0.6959(5) 0.4212(3) 0.0312(10) Uani 1 1 d . . . C24 C 0.5997(3) 0.7840(6) 0.4738(3) 0.0406(11) Uani 1 1 d . . . H24 H 0.6542 0.8081 0.4590 0.049 Uiso 1 1 calc R . . C25 C 0.5860(4) 0.8339(7) 0.5483(3) 0.0496(13) Uani 1 1 d . . . H25 H 0.6318 0.8942 0.5846 0.060 Uiso 1 1 calc R . . C26 C 0.5042(4) 0.7955(6) 0.5708(3) 0.0474(13) Uani 1 1 d . . . H26 H 0.4975 0.8303 0.6221 0.057 Uiso 1 1 calc R . . C27 C 0.4338(3) 0.7081(6) 0.5193(3) 0.0387(11) Uani 1 1 d . . . H27 H 0.3800 0.6830 0.5349 0.046 Uiso 1 1 calc R . . C28 C 0.5894(3) 0.6454(7) 0.2970(3) 0.0463(13) Uani 1 1 d . . . H28A H 0.6436 0.6994 0.3314 0.069 Uiso 1 1 calc R . . H28B H 0.5628 0.6963 0.2438 0.069 Uiso 1 1 calc R . . H28C H 0.6089 0.5476 0.2861 0.069 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 Cd1 0.0323(2) 0.03042(19) 0.0300(2) 0.00047(13) 0.00932(15) 0.00149(13) Br1 0.0525(3) 0.0384(3) 0.0385(3) 0.0030(2) -0.0008(2) 0.0072(2) Br2 0.0472(3) 0.0480(3) 0.0388(3) -0.0116(2) 0.0178(2) -0.0001(2) N1 0.035(2) 0.0304(19) 0.030(2) 0.0014(16) 0.0116(17) 0.0003(16) C1 0.039(2) 0.029(2) 0.028(2) -0.0024(18) 0.014(2) -0.0011(18) C2 0.030(2) 0.028(2) 0.026(2) -0.0027(17) 0.0084(19) 0.0015(17) C3 0.033(2) 0.027(2) 0.036(3) -0.0006(18) 0.016(2) -0.0004(18) C4 0.033(2) 0.030(2) 0.024(2) 0.0029(17) 0.0092(19) 0.0047(18) C5 0.034(2) 0.032(2) 0.025(2) -0.0029(18) 0.0070(19) 0.0000(18) N11 0.041(2) 0.039(2) 0.028(2) 0.0004(17) 0.0116(18) 0.0009(17) N12 0.033(2) 0.032(2) 0.035(2) 0.0013(16) 0.0130(17) 0.0019(16) C11 0.034(2) 0.029(2) 0.034(3) 0.0022(18) 0.015(2) 0.0060(18) C12 0.039(3) 0.035(2) 0.030(2) 0.0015(19) 0.016(2) 0.006(2) C13 0.037(2) 0.037(2) 0.032(2) 0.006(2) 0.017(2) 0.011(2) C14 0.056(3) 0.042(3) 0.047(3) 0.003(2) 0.028(3) 0.005(2) C15 0.070(4) 0.054(3) 0.042(3) 0.012(3) 0.030(3) 0.009(3) C16 0.070(4) 0.070(4) 0.033(3) 0.009(3) 0.023(3) 0.021(3) C17 0.056(3) 0.050(3) 0.032(3) 0.002(2) 0.015(2) 0.010(3) C18 0.041(3) 0.055(3) 0.040(3) 0.001(2) 0.017(2) -0.009(2) N21 0.0303(19) 0.0277(18) 0.0263(19) -0.0024(14) 0.0090(16) -0.0023(15) N22 0.0272(18) 0.034(2) 0.031(2) -0.0003(16) 0.0090(16) -0.0003(15) C21 0.036(2) 0.029(2) 0.022(2) -0.0003(17) 0.0096(19) 0.0006(18) C22 0.026(2) 0.032(2) 0.029(2) -0.0019(18) 0.0060(18) -0.0012(17) C23 0.031(2) 0.035(2) 0.027(2) -0.0007(18) 0.0077(19) 0.0015(18) C24 0.033(2) 0.050(3) 0.038(3) -0.004(2) 0.009(2) -0.008(2) C25 0.042(3) 0.058(3) 0.042(3) -0.019(3) 0.003(2) -0.016(3) C26 0.046(3) 0.060(3) 0.035(3) -0.021(2) 0.011(2) -0.006(2) C27 0.037(3) 0.050(3) 0.030(2) -0.006(2) 0.010(2) -0.004(2) C28 0.029(2) 0.077(4) 0.036(3) 0.000(3) 0.015(2) -0.002(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 Cd1 N21 2.216(3) 2_545 ? Cd1 N1 2.338(4) . ? Cd1 Br1 2.5160(6) . ? Cd1 Br2 2.5412(6) . ? N1 C5 1.332(5) . ? N1 C1 1.337(5) . ? C1 C2 1.402(6) . ? C2 C3 1.391(6) . ? C2 C21 1.458(6) . ? C3 C4 1.380(6) . ? C4 C5 1.398(6) . ? C4 C11 1.477(6) . ? N11 C11 1.311(6) . ? N11 C12 1.392(6) . ? N12 C11 1.376(6) . ? N12 C13 1.382(6) . ? N12 C18 1.457(6) . ? C12 C13 1.392(7) . ? C12 C17 1.398(7) . ? C13 C14 1.388(6) . ? C14 C15 1.387(7) . ? C15 C16 1.390(9) . ? C16 C17 1.368(7) . ? N21 C21 1.336(5) . ? N21 C22 1.383(5) . ? N21 Cd1 2.216(3) 2 ? N22 C21 1.362(6) . ? N22 C23 1.367(6) . ? N22 C28 1.465(5) . ? C22 C27 1.396(6) . ? C22 C23 1.399(6) . ? C23 C24 1.390(6) . ? C24 C25 1.370(7) . ? C25 C26 1.403(7) . ? C26 C27 1.373(7) . ? 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 N21 Cd1 N1 100.78(13) 2_545 . ? N21 Cd1 Br1 118.39(9) 2_545 . ? N1 Cd1 Br1 101.97(9) . . ? N21 Cd1 Br2 116.35(9) 2_545 . ? N1 Cd1 Br2 98.62(9) . . ? Br1 Cd1 Br2 115.57(2) . . ? C5 N1 C1 119.3(4) . . ? C5 N1 Cd1 118.3(3) . . ? C1 N1 Cd1 121.8(3) . . ? N1 C1 C2 121.5(4) . . ? C3 C2 C1 118.2(4) . . ? C3 C2 C21 121.2(4) . . ? C1 C2 C21 120.6(4) . . ? C4 C3 C2 120.5(4) . . ? C3 C4 C5 117.1(4) . . ? C3 C4 C11 125.3(4) . . ? C5 C4 C11 117.7(4) . . ? N1 C5 C4 123.3(4) . . ? C11 N11 C12 104.8(4) . . ? C11 N12 C13 105.8(4) . . ? C11 N12 C18 130.3(4) . . ? C13 N12 C18 123.8(4) . . ? N11 C11 N12 113.5(4) . . ? N11 C11 C4 122.4(4) . . ? N12 C11 C4 124.1(4) . . ? C13 C12 N11 109.9(4) . . ? C13 C12 C17 120.2(4) . . ? N11 C12 C17 129.9(5) . . ? N12 C13 C14 132.0(5) . . ? N12 C13 C12 106.0(4) . . ? C14 C13 C12 122.0(4) . . ? C15 C14 C13 116.8(5) . . ? C14 C15 C16 121.3(5) . . ? C17 C16 C15 121.8(5) . . ? C16 C17 C12 117.8(5) . . ? C21 N21 C22 106.7(3) . . ? C21 N21 Cd1 132.0(3) . 2 ? C22 N21 Cd1 118.7(3) . 2 ? C21 N22 C23 108.6(3) . . ? C21 N22 C28 127.8(4) . . ? C23 N22 C28 123.6(4) . . ? N21 C21 N22 110.3(4) . . ? N21 C21 C2 126.6(4) . . ? N22 C21 C2 123.1(4) . . ? N21 C22 C27 131.2(4) . . ? N21 C22 C23 108.7(4) . . ? C27 C22 C23 120.1(4) . . ? N22 C23 C24 132.1(4) . . ? N22 C23 C22 105.7(4) . . ? C24 C23 C22 122.1(4) . . ? C25 C24 C23 117.2(4) . . ? C24 C25 C26 121.1(5) . . ? C27 C26 C25 122.0(4) . . ? C26 C27 C22 117.4(4) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.692 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 952908' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 Cl2 Hg N5' _chemical_formula_weight 610.89 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' 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 14.578(3) _cell_length_b 8.8123(16) _cell_length_c 16.385(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.323(6) _cell_angle_gamma 90.00 _cell_volume 1998.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 7.989 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.194 _exptl_absorpt_correction_T_max 0.354 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23838 _diffrn_reflns_av_R_equivalents 0.0956 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3717 _reflns_number_gt 2568 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1000P)^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 3717 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 0.817 _refine_ls_restrained_S_all 0.817 _refine_ls_shift/su_max 0.010 _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 0.26040(3) 0.03133(4) 0.12954(2) 0.04290(17) Uani 1 1 d . . . Cl2A Cl 0.37579(19) -0.0734(3) 0.25567(15) 0.0530(7) Uani 1 1 d . . . Cl1 Cl 0.2918(2) -0.0088(3) -0.00655(16) 0.0538(7) Uani 1 1 d . . . N1 N 0.3151(5) 0.2969(8) 0.1462(4) 0.0376(17) Uani 1 1 d . . . C1 C 0.3220(6) 0.3713(10) 0.0768(5) 0.039(2) Uani 1 1 d . . . H1 H 0.2959 0.3257 0.0233 0.047 Uiso 1 1 calc R . . C2 C 0.3655(7) 0.5110(9) 0.0801(6) 0.035(2) Uani 1 1 d . . . C3 C 0.4015(6) 0.5799(10) 0.1612(5) 0.037(2) Uani 1 1 d . . . H3 H 0.4279 0.6768 0.1659 0.045 Uiso 1 1 calc R . . C4 C 0.3980(6) 0.5049(10) 0.2337(6) 0.037(2) Uani 1 1 d . . . C5 C 0.3528(6) 0.3624(10) 0.2225(5) 0.038(2) Uani 1 1 d . . . H5 H 0.3489 0.3111 0.2710 0.046 Uiso 1 1 calc R . . N11 N 0.3041(6) 0.5418(9) -0.0752(5) 0.047(2) Uani 1 1 d . . . N12 N 0.4361(5) 0.6847(8) -0.0077(5) 0.0400(18) Uani 1 1 d . . . C11 C 0.3693(7) 0.5815(11) -0.0004(5) 0.042(2) Uani 1 1 d . . . C12 C 0.4128(7) 0.7183(10) -0.0946(6) 0.043(2) Uani 1 1 d . . . C13 C 0.3314(6) 0.6296(11) -0.1348(6) 0.043(2) Uani 1 1 d . . . C14 C 0.2894(8) 0.6409(14) -0.2256(6) 0.062(3) Uani 1 1 d . . . H14 H 0.2357 0.5838 -0.2554 0.075 Uiso 1 1 calc R . . C15 C 0.3330(10) 0.7422(17) -0.2675(8) 0.077(4) Uani 1 1 d . . . H15 H 0.3074 0.7519 -0.3269 0.092 Uiso 1 1 calc R . . C16 C 0.4120(11) 0.8280(15) -0.2248(8) 0.077(4) Uani 1 1 d . . . H16 H 0.4370 0.8948 -0.2563 0.093 Uiso 1 1 calc R . . C17 C 0.4556(8) 0.8197(12) -0.1377(7) 0.057(3) Uani 1 1 d . . . H17 H 0.5096 0.8772 -0.1092 0.068 Uiso 1 1 calc R . . C18 C 0.5205(10) 0.7490(16) 0.0607(8) 0.087(4) Uani 1 1 d . . . H18A H 0.5540 0.8197 0.0355 0.131 Uiso 1 1 calc R . . H18B H 0.5636 0.6685 0.0880 0.131 Uiso 1 1 calc R . . H18C H 0.4983 0.8004 0.1027 0.131 Uiso 1 1 calc R . . N21 N 0.3903(5) 0.5819(9) 0.3778(4) 0.0386(17) Uani 1 1 d . . . N22 N 0.5220(5) 0.6446(9) 0.3464(4) 0.0403(18) Uani 1 1 d . . . C21 C 0.4362(7) 0.5743(10) 0.3188(5) 0.036(2) Uani 1 1 d . . . C22 C 0.4501(6) 0.6659(10) 0.4455(5) 0.036(2) Uani 1 1 d . . . C23 C 0.5307(6) 0.7060(9) 0.4260(5) 0.035(2) Uani 1 1 d . . . C24 C 0.6044(7) 0.7961(11) 0.4806(6) 0.048(2) Uani 1 1 d . . . H24 H 0.6601 0.8211 0.4675 0.058 Uiso 1 1 calc R . . C25 C 0.5883(7) 0.8449(12) 0.5549(6) 0.054(3) Uani 1 1 d . . . H25 H 0.6338 0.9076 0.5924 0.064 Uiso 1 1 calc R . . C26 C 0.5061(8) 0.8032(12) 0.5757(6) 0.052(3) Uani 1 1 d . . . H26 H 0.4989 0.8365 0.6272 0.062 Uiso 1 1 calc R . . C27 C 0.4359(7) 0.7142(11) 0.5218(5) 0.045(2) Uani 1 1 d . . . H27 H 0.3808 0.6870 0.5355 0.053 Uiso 1 1 calc R . . C28 C 0.5951(8) 0.6585(14) 0.3028(7) 0.064(3) Uani 1 1 d . . . H28A H 0.6494 0.7147 0.3385 0.095 Uiso 1 1 calc R . . H28B H 0.5680 0.7108 0.2492 0.095 Uiso 1 1 calc R . . H28C H 0.6159 0.5593 0.2921 0.095 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 Hg1 0.0479(2) 0.0411(2) 0.0405(2) 0.00207(16) 0.01509(17) 0.00335(17) Cl2A 0.0659(16) 0.0428(14) 0.0399(13) 0.0019(10) 0.0016(11) 0.0092(11) Cl1 0.0644(16) 0.0586(16) 0.0459(14) -0.0125(11) 0.0281(13) -0.0037(12) N1 0.046(5) 0.032(4) 0.035(4) -0.006(3) 0.014(3) -0.006(3) C1 0.053(6) 0.041(6) 0.025(4) -0.006(4) 0.014(4) -0.001(4) C2 0.044(5) 0.020(4) 0.045(5) 0.000(4) 0.021(4) 0.006(3) C3 0.052(5) 0.027(4) 0.035(5) -0.007(4) 0.017(4) -0.006(4) C4 0.038(5) 0.043(6) 0.033(5) -0.003(4) 0.016(4) 0.004(4) C5 0.055(6) 0.035(5) 0.030(4) 0.005(4) 0.022(4) 0.002(4) N11 0.056(5) 0.051(5) 0.043(5) 0.007(4) 0.027(4) 0.008(4) N12 0.040(4) 0.042(5) 0.045(4) 0.004(4) 0.023(4) 0.005(3) C11 0.056(6) 0.044(5) 0.029(5) 0.004(4) 0.019(4) 0.007(5) C12 0.055(6) 0.037(5) 0.047(5) 0.009(4) 0.032(5) 0.016(4) C13 0.040(5) 0.053(6) 0.040(5) -0.002(4) 0.019(4) 0.005(4) C14 0.079(8) 0.072(8) 0.042(6) -0.010(5) 0.027(5) 0.016(6) C15 0.097(10) 0.098(10) 0.045(7) 0.022(7) 0.037(7) 0.023(8) C16 0.118(12) 0.073(9) 0.062(8) 0.026(7) 0.058(8) 0.022(8) C17 0.070(7) 0.049(6) 0.066(7) 0.012(5) 0.044(6) -0.001(5) C18 0.114(12) 0.077(9) 0.093(10) 0.006(7) 0.063(9) -0.002(8) N21 0.042(4) 0.040(4) 0.028(4) 0.001(3) 0.003(3) -0.002(3) N22 0.051(5) 0.043(5) 0.029(4) 0.000(3) 0.016(3) 0.001(4) C21 0.047(5) 0.031(5) 0.029(4) -0.003(4) 0.010(4) 0.003(4) C22 0.042(5) 0.036(5) 0.029(4) 0.003(4) 0.011(4) 0.004(4) C23 0.044(5) 0.027(5) 0.033(5) 0.002(4) 0.014(4) 0.007(4) C24 0.039(5) 0.052(6) 0.052(6) 0.001(5) 0.012(5) -0.006(4) C25 0.059(7) 0.057(7) 0.041(5) -0.016(5) 0.010(5) -0.011(5) C26 0.067(7) 0.054(7) 0.036(5) -0.009(5) 0.018(5) -0.007(5) C27 0.051(6) 0.054(6) 0.028(5) 0.002(4) 0.013(4) 0.008(5) C28 0.066(7) 0.074(8) 0.056(6) -0.004(6) 0.026(6) -0.002(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 Hg1 N21 2.208(7) 2_545 ? Hg1 Cl2A 2.401(2) . ? Hg1 Cl1 2.439(3) . ? Hg1 N1 2.460(7) . ? N1 C5 1.329(10) . ? N1 C1 1.343(10) . ? C1 C2 1.378(12) . ? C2 C3 1.405(12) . ? C2 C11 1.475(12) . ? C3 C4 1.374(12) . ? C4 C5 1.404(12) . ? C4 C21 1.462(12) . ? N11 C11 1.339(12) . ? N11 C13 1.398(12) . ? N12 C11 1.365(12) . ? N12 C12 1.387(11) . ? N12 C18 1.492(15) . ? C12 C13 1.401(13) . ? C12 C17 1.401(13) . ? C13 C14 1.423(12) . ? C14 C15 1.395(17) . ? C15 C16 1.371(18) . ? C16 C17 1.369(15) . ? N21 C21 1.338(11) . ? N21 C22 1.389(10) . ? N21 Hg1 2.208(7) 2 ? N22 C21 1.342(11) . ? N22 C23 1.381(10) . ? N22 C28 1.462(12) . ? C22 C23 1.357(12) . ? C22 C27 1.397(12) . ? C23 C24 1.407(12) . ? C24 C25 1.378(13) . ? C25 C26 1.394(14) . ? C26 C27 1.369(13) . ? 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 N21 Hg1 Cl2A 122.70(19) 2_545 . ? N21 Hg1 Cl1 116.71(18) 2_545 . ? Cl2A Hg1 Cl1 116.67(9) . . ? N21 Hg1 N1 95.5(3) 2_545 . ? Cl2A Hg1 N1 98.92(18) . . ? Cl1 Hg1 N1 95.27(17) . . ? C5 N1 C1 117.8(7) . . ? C5 N1 Hg1 122.7(6) . . ? C1 N1 Hg1 118.6(5) . . ? N1 C1 C2 124.0(8) . . ? C1 C2 C3 116.9(8) . . ? C1 C2 C11 119.2(8) . . ? C3 C2 C11 123.8(8) . . ? C4 C3 C2 120.4(8) . . ? C3 C4 C5 117.4(8) . . ? C3 C4 C21 121.1(8) . . ? C5 C4 C21 121.4(8) . . ? N1 C5 C4 123.3(8) . . ? C11 N11 C13 102.6(8) . . ? C11 N12 C12 106.3(7) . . ? C11 N12 C18 129.1(8) . . ? C12 N12 C18 124.6(8) . . ? N11 C11 N12 114.5(8) . . ? N11 C11 C2 119.5(9) . . ? N12 C11 C2 126.0(8) . . ? C13 C12 C17 124.3(9) . . ? C13 C12 N12 105.2(8) . . ? C17 C12 N12 130.5(10) . . ? N11 C13 C12 111.4(8) . . ? N11 C13 C14 130.2(9) . . ? C12 C13 C14 118.4(9) . . ? C15 C14 C13 116.5(11) . . ? C16 C15 C14 122.7(11) . . ? C17 C16 C15 122.9(11) . . ? C16 C17 C12 115.2(11) . . ? C21 N21 C22 105.8(7) . . ? C21 N21 Hg1 131.7(6) . 2 ? C22 N21 Hg1 121.0(6) . 2 ? C21 N22 C23 107.4(7) . . ? C21 N22 C28 128.3(8) . . ? C23 N22 C28 124.3(8) . . ? N22 C21 N21 111.0(7) . . ? N22 C21 C4 123.4(8) . . ? N21 C21 C4 125.6(8) . . ? C23 C22 N21 108.9(7) . . ? C23 C22 C27 120.9(8) . . ? N21 C22 C27 130.2(9) . . ? C22 C23 N22 106.9(8) . . ? C22 C23 C24 122.8(8) . . ? N22 C23 C24 130.3(9) . . ? C25 C24 C23 115.5(9) . . ? C24 C25 C26 122.1(9) . . ? C27 C26 C25 121.3(9) . . ? C26 C27 C22 117.4(9) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.097 _refine_diff_density_min -1.297 _refine_diff_density_rms 0.152 _database_code_depnum_ccdc_archive 'CCDC 952909' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 Br2 Hg N5' _chemical_formula_weight 699.81 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 14.706(2) _cell_length_b 9.0229(14) _cell_length_c 16.359(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.064(4) _cell_angle_gamma 90.00 _cell_volume 2075.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 11.286 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.055 _exptl_absorpt_correction_T_max 0.184 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24656 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0230 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3856 _reflns_number_gt 3378 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1000P)^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 0.00065(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3856 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0284 _refine_ls_R_factor_gt 0.0218 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0809 _refine_ls_goodness_of_fit_ref 0.732 _refine_ls_restrained_S_all 0.732 _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 0.263932(12) 0.03181(2) 0.128768(11) 0.03313(11) Uani 1 1 d . . . Br1 Br 0.38074(4) -0.06952(6) 0.26138(3) 0.04724(16) Uani 1 1 d . . . Br2 Br 0.29817(4) -0.00855(6) -0.01308(3) 0.04314(15) Uani 1 1 d . . . N1 N 0.3135(3) 0.2950(4) 0.1445(2) 0.0321(8) Uani 1 1 d . . . C1 C 0.3190(3) 0.3685(5) 0.0752(3) 0.0311(9) Uani 1 1 d . . . H1 H 0.2949 0.3231 0.0222 0.037 Uiso 1 1 calc R . . C2 C 0.3589(3) 0.5092(5) 0.0776(3) 0.0291(9) Uani 1 1 d . . . C3 C 0.3941(3) 0.5761(5) 0.1579(3) 0.0290(9) Uani 1 1 d . . . H3 H 0.4192 0.6714 0.1625 0.035 Uiso 1 1 calc R . . C4 C 0.3914(3) 0.4982(5) 0.2311(3) 0.0297(9) Uani 1 1 d . . . C5 C 0.3507(3) 0.3568(5) 0.2210(3) 0.0305(9) Uani 1 1 d . . . H5 H 0.3495 0.3039 0.2695 0.037 Uiso 1 1 calc R . . N11 N 0.2977(3) 0.5452(4) -0.0767(2) 0.0339(9) Uani 1 1 d . . . N12 N 0.4304(2) 0.6729(4) -0.0114(2) 0.0322(8) Uani 1 1 d . . . C11 C 0.3614(3) 0.5778(5) -0.0033(3) 0.0292(9) Uani 1 1 d . . . C12 C 0.4064(3) 0.7086(5) -0.0972(3) 0.0338(10) Uani 1 1 d . . . C13 C 0.3242(3) 0.6275(5) -0.1369(3) 0.0331(10) Uani 1 1 d . . . C14 C 0.2807(4) 0.6410(6) -0.2246(3) 0.0459(12) Uani 1 1 d . . . H14 H 0.2269 0.5860 -0.2519 0.055 Uiso 1 1 calc R . . C15 C 0.3203(4) 0.7385(7) -0.2694(3) 0.0540(14) Uani 1 1 d . . . H15 H 0.2917 0.7511 -0.3277 0.065 Uiso 1 1 calc R . . C16 C 0.4027(4) 0.8191(7) -0.2288(3) 0.0561(15) Uani 1 1 d . . . H16 H 0.4279 0.8833 -0.2610 0.067 Uiso 1 1 calc R . . C17 C 0.4471(4) 0.8057(6) -0.1428(3) 0.0467(12) Uani 1 1 d . . . H17 H 0.5019 0.8591 -0.1162 0.056 Uiso 1 1 calc R . . C18 C 0.5122(3) 0.7326(6) 0.0539(3) 0.0444(12) Uani 1 1 d . . . H18A H 0.5450 0.8023 0.0283 0.067 Uiso 1 1 calc R . . H18B H 0.5546 0.6532 0.0794 0.067 Uiso 1 1 calc R . . H18C H 0.4910 0.7815 0.0971 0.067 Uiso 1 1 calc R . . N21 N 0.3856(2) 0.5745(4) 0.3755(2) 0.0288(7) Uani 1 1 d . . . N22 N 0.5171(2) 0.6320(4) 0.3412(2) 0.0294(8) Uani 1 1 d . . . C21 C 0.4305(3) 0.5641(5) 0.3155(3) 0.0271(9) Uani 1 1 d . . . C22 C 0.4455(3) 0.6559(5) 0.4420(2) 0.0293(9) Uani 1 1 d . . . C23 C 0.5271(3) 0.6927(5) 0.4200(3) 0.0299(9) Uani 1 1 d . . . C24 C 0.5986(3) 0.7821(6) 0.4722(3) 0.0396(11) Uani 1 1 d . . . H24 H 0.6526 0.8074 0.4567 0.048 Uiso 1 1 calc R . . C25 C 0.5851(4) 0.8312(7) 0.5482(3) 0.0517(13) Uani 1 1 d . . . H25 H 0.6312 0.8903 0.5848 0.062 Uiso 1 1 calc R . . C26 C 0.5034(4) 0.7933(7) 0.5705(3) 0.0462(13) Uani 1 1 d . . . H26 H 0.4968 0.8282 0.6220 0.055 Uiso 1 1 calc R . . C27 C 0.4323(3) 0.7062(6) 0.5192(3) 0.0363(10) Uani 1 1 d . . . H27 H 0.3782 0.6819 0.5348 0.044 Uiso 1 1 calc R . . C28 C 0.5883(3) 0.6442(7) 0.2958(3) 0.0448(12) Uani 1 1 d . . . H28A H 0.6420 0.6989 0.3301 0.067 Uiso 1 1 calc R . . H28B H 0.5615 0.6949 0.2426 0.067 Uiso 1 1 calc R . . H28C H 0.6084 0.5469 0.2849 0.067 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 Hg1 0.03302(14) 0.03293(16) 0.03254(15) 0.00106(6) 0.00820(9) 0.00304(6) Br1 0.0531(3) 0.0381(3) 0.0388(3) 0.0020(2) -0.0046(2) 0.0067(2) Br2 0.0460(3) 0.0485(3) 0.0382(3) -0.0107(2) 0.0175(2) -0.0002(2) N1 0.038(2) 0.027(2) 0.0332(19) -0.0027(15) 0.0135(16) -0.0011(16) C1 0.034(2) 0.035(2) 0.0243(19) -0.0054(18) 0.0078(16) -0.0014(19) C2 0.030(2) 0.028(2) 0.032(2) -0.0028(18) 0.0124(19) 0.0022(17) C3 0.033(2) 0.025(2) 0.031(2) -0.0036(18) 0.0125(18) 0.0011(18) C4 0.032(2) 0.031(2) 0.028(2) -0.0041(18) 0.0114(19) 0.0023(18) C5 0.036(2) 0.028(2) 0.029(2) 0.0027(17) 0.0112(17) -0.0003(18) N11 0.036(2) 0.036(2) 0.029(2) -0.0025(15) 0.0080(17) -0.0040(16) N12 0.0304(18) 0.032(2) 0.0344(19) 0.0017(16) 0.0105(15) -0.0012(16) C11 0.030(2) 0.027(2) 0.032(2) -0.0038(18) 0.0106(17) 0.0022(18) C12 0.036(2) 0.037(3) 0.034(2) 0.0051(19) 0.0191(19) 0.0085(19) C13 0.038(2) 0.037(3) 0.028(2) -0.0007(18) 0.0157(18) 0.0076(19) C14 0.051(3) 0.052(3) 0.035(2) -0.002(2) 0.013(2) 0.007(2) C15 0.069(4) 0.066(4) 0.030(3) 0.004(3) 0.018(3) 0.016(3) C16 0.076(4) 0.061(4) 0.045(3) 0.010(3) 0.038(3) 0.004(3) C17 0.053(3) 0.043(3) 0.052(3) 0.007(2) 0.027(2) 0.004(2) C18 0.035(2) 0.056(3) 0.044(3) -0.002(2) 0.014(2) -0.012(2) N21 0.0313(18) 0.0322(19) 0.0226(17) -0.0002(15) 0.0075(14) -0.0013(16) N22 0.0261(17) 0.035(2) 0.0278(17) 0.0006(15) 0.0082(14) 0.0007(15) C21 0.028(2) 0.026(2) 0.026(2) -0.0008(17) 0.0051(17) 0.0007(17) C22 0.031(2) 0.030(2) 0.024(2) -0.0009(17) 0.0045(16) -0.0008(18) C23 0.028(2) 0.033(2) 0.025(2) 0.0002(17) 0.0015(17) 0.0033(18) C24 0.025(2) 0.050(3) 0.039(2) -0.006(2) 0.0018(19) -0.011(2) C25 0.047(3) 0.063(4) 0.038(3) -0.015(3) 0.001(2) -0.015(3) C26 0.046(3) 0.058(4) 0.035(2) -0.019(2) 0.012(2) -0.007(2) C27 0.038(2) 0.046(3) 0.024(2) -0.0048(19) 0.0085(18) -0.003(2) C28 0.030(2) 0.070(4) 0.036(2) -0.004(2) 0.0128(19) 0.003(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 Hg1 N21 2.214(3) 2_545 ? Hg1 N1 2.475(4) . ? Hg1 Br1 2.5112(6) . ? Hg1 Br2 2.5411(6) . ? N1 C1 1.337(5) . ? N1 C5 1.331(5) . ? C1 C2 1.394(6) . ? C2 C3 1.399(6) . ? C2 C11 1.471(6) . ? C3 C4 1.399(6) . ? C4 C5 1.399(6) . ? C4 C21 1.458(6) . ? N11 C11 1.320(6) . ? N11 C13 1.377(6) . ? N12 C12 1.380(5) . ? N12 C11 1.366(5) . ? N12 C18 1.458(6) . ? C12 C17 1.395(6) . ? C12 C13 1.400(6) . ? C13 C14 1.394(6) . ? C14 C15 1.379(7) . ? C15 C16 1.403(8) . ? C16 C17 1.370(7) . ? N21 C21 1.336(5) . ? N21 C22 1.391(5) . ? N21 Hg1 2.214(3) 2 ? N22 C21 1.364(5) . ? N22 C23 1.368(5) . ? N22 C28 1.454(5) . ? C22 C23 1.391(6) . ? C22 C27 1.408(5) . ? C23 C24 1.399(6) . ? C24 C25 1.388(7) . ? C25 C26 1.397(7) . ? C26 C27 1.379(6) . ? 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 N21 Hg1 N1 95.50(13) 2_545 . ? N21 Hg1 Br1 120.78(9) 2_545 . ? N1 Hg1 Br1 98.83(8) . . ? N21 Hg1 Br2 117.24(9) 2_545 . ? N1 Hg1 Br2 95.83(8) . . ? Br1 Hg1 Br2 117.91(2) . . ? C1 N1 C5 118.6(4) . . ? C1 N1 Hg1 118.5(3) . . ? C5 N1 Hg1 121.8(3) . . ? N1 C1 C2 123.9(4) . . ? C3 C2 C1 117.1(4) . . ? C3 C2 C11 124.3(4) . . ? C1 C2 C11 118.6(4) . . ? C4 C3 C2 119.4(4) . . ? C3 C4 C5 118.4(4) . . ? C3 C4 C21 120.3(4) . . ? C5 C4 C21 121.3(4) . . ? N1 C5 C4 122.5(4) . . ? C11 N11 C13 104.8(4) . . ? C12 N12 C11 105.7(3) . . ? C12 N12 C18 124.7(4) . . ? C11 N12 C18 129.6(4) . . ? N11 C11 N12 113.6(4) . . ? N11 C11 C2 121.7(4) . . ? N12 C11 C2 124.6(4) . . ? N12 C12 C17 132.0(4) . . ? N12 C12 C13 106.1(4) . . ? C17 C12 C13 121.9(4) . . ? C14 C13 C12 120.3(4) . . ? C14 C13 N11 130.0(5) . . ? C12 C13 N11 109.7(4) . . ? C13 C14 C15 117.7(5) . . ? C16 C15 C14 121.3(5) . . ? C15 C16 C17 121.7(5) . . ? C12 C17 C16 117.0(5) . . ? C21 N21 C22 106.0(3) . . ? C21 N21 Hg1 131.7(3) . 2 ? C22 N21 Hg1 120.7(3) . 2 ? C21 N22 C23 107.6(3) . . ? C21 N22 C28 128.6(4) . . ? C23 N22 C28 123.7(4) . . ? N21 C21 N22 111.1(4) . . ? N21 C21 C4 125.6(4) . . ? N22 C21 C4 123.2(4) . . ? N21 C22 C23 108.6(3) . . ? N21 C22 C27 130.5(4) . . ? C23 C22 C27 120.7(4) . . ? N22 C23 C22 106.6(4) . . ? N22 C23 C24 131.3(4) . . ? C22 C23 C24 122.1(4) . . ? C25 C24 C23 116.8(4) . . ? C24 C25 C26 121.1(4) . . ? C27 C26 C25 122.4(4) . . ? C26 C27 C22 116.8(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.125 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 952910' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H17 Hg I2 N5' _chemical_formula_weight 793.79 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' I I -0.4742 1.8119 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 14.586(5) _cell_length_b 9.650(3) _cell_length_c 16.442(6) _cell_angle_alpha 90.00 _cell_angle_beta 105.081(11) _cell_angle_gamma 90.00 _cell_volume 2234.5(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rectangular blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 9.669 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.135 _exptl_absorpt_correction_T_max 0.258 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25744 _diffrn_reflns_av_R_equivalents 0.1095 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4150 _reflns_number_gt 2674 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1000P)^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 4150 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 0.792 _refine_ls_restrained_S_all 0.792 _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 0.27875(3) 0.03225(4) 0.13254(2) 0.04257(17) Uani 1 1 d . . . I1 I 0.39641(6) -0.06470(8) 0.27319(4) 0.0566(3) Uani 1 1 d . . . I2 I 0.31726(6) -0.00344(8) -0.01774(4) 0.0524(2) Uani 1 1 d . . . N1 N 0.3152(6) 0.2882(8) 0.1480(5) 0.0381(19) Uani 1 1 d . . . C1 C 0.3136(7) 0.3595(9) 0.0783(6) 0.037(2) Uani 1 1 d . . . H1 H 0.2880 0.3176 0.0264 0.044 Uiso 1 1 calc R . . C2 C 0.3489(7) 0.4952(10) 0.0795(6) 0.037(2) Uani 1 1 d . . . C3 C 0.3819(8) 0.5599(10) 0.1567(6) 0.042(3) Uani 1 1 d . . . H3 H 0.4021 0.6517 0.1600 0.051 Uiso 1 1 calc R . . C4 C 0.3842(8) 0.4837(10) 0.2299(6) 0.040(2) Uani 1 1 d . . . C5 C 0.3496(8) 0.3509(10) 0.2228(6) 0.043(3) Uani 1 1 d . . . H5 H 0.3498 0.3022 0.2717 0.052 Uiso 1 1 calc R . . N11 N 0.2825(6) 0.5337(9) -0.0716(5) 0.041(2) Uani 1 1 d . . . N12 N 0.4172(6) 0.6459(8) -0.0144(5) 0.039(2) Uani 1 1 d . . . C11 C 0.3501(8) 0.5614(10) -0.0024(6) 0.040(3) Uani 1 1 d . . . C12 C 0.3921(8) 0.6812(11) -0.0980(6) 0.044(3) Uani 1 1 d . . . C13 C 0.3082(8) 0.6107(11) -0.1331(6) 0.045(3) Uani 1 1 d . . . C14 C 0.2636(9) 0.6279(12) -0.2188(7) 0.056(3) Uani 1 1 d . . . H14 H 0.2078 0.5805 -0.2434 0.067 Uiso 1 1 calc R . . C15 C 0.3030(12) 0.7155(15) -0.2660(7) 0.074(4) Uani 1 1 d . . . H15 H 0.2730 0.7293 -0.3227 0.089 Uiso 1 1 calc R . . C16 C 0.3869(11) 0.7831(14) -0.2299(7) 0.069(4) Uani 1 1 d . . . H16 H 0.4132 0.8402 -0.2634 0.083 Uiso 1 1 calc R . . C17 C 0.4326(9) 0.7694(12) -0.1468(7) 0.056(3) Uani 1 1 d . . . H17 H 0.4886 0.8170 -0.1232 0.067 Uiso 1 1 calc R . . C18 C 0.5014(8) 0.6966(12) 0.0471(7) 0.051(3) Uani 1 1 d . . . H18A H 0.5362 0.7574 0.0198 0.077 Uiso 1 1 calc R . . H18B H 0.5408 0.6196 0.0712 0.077 Uiso 1 1 calc R . . H18C H 0.4826 0.7461 0.0907 0.077 Uiso 1 1 calc R . . N21 N 0.3771(6) 0.5641(8) 0.3736(4) 0.0340(19) Uani 1 1 d . . . N22 N 0.5104(6) 0.6086(9) 0.3359(4) 0.039(2) Uani 1 1 d . . . C21 C 0.4220(8) 0.5487(10) 0.3132(5) 0.038(2) Uani 1 1 d . . . C22 C 0.4386(7) 0.6411(11) 0.4371(5) 0.039(2) Uani 1 1 d . . . C23 C 0.5207(7) 0.6676(11) 0.4141(6) 0.039(2) Uani 1 1 d . . . C24 C 0.5929(8) 0.7496(12) 0.4632(6) 0.050(3) Uani 1 1 d . . . H24 H 0.6474 0.7705 0.4464 0.060 Uiso 1 1 calc R . . C25 C 0.5792(9) 0.7974(13) 0.5370(7) 0.061(3) Uani 1 1 d . . . H25 H 0.6264 0.8510 0.5719 0.073 Uiso 1 1 calc R . . C26 C 0.4976(9) 0.7692(14) 0.5619(7) 0.058(3) Uani 1 1 d . . . H26 H 0.4917 0.8041 0.6130 0.069 Uiso 1 1 calc R . . C27 C 0.4251(8) 0.6913(11) 0.5134(6) 0.051(3) Uani 1 1 d . . . H27 H 0.3701 0.6728 0.5301 0.061 Uiso 1 1 calc R . . C28 C 0.5823(8) 0.6105(14) 0.2897(6) 0.058(3) Uani 1 1 d . . . H28A H 0.6369 0.6604 0.3214 0.086 Uiso 1 1 calc R . . H28B H 0.5575 0.6552 0.2364 0.086 Uiso 1 1 calc R . . H28C H 0.6003 0.5172 0.2807 0.086 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 Hg1 0.0512(3) 0.0330(3) 0.0393(2) 0.00136(16) 0.00416(18) 0.00361(19) I1 0.0670(6) 0.0395(5) 0.0494(4) 0.0049(3) -0.0098(4) 0.0038(4) I2 0.0644(6) 0.0485(5) 0.0435(4) -0.0089(3) 0.0126(4) 0.0049(4) N1 0.049(5) 0.021(4) 0.044(4) -0.004(3) 0.011(4) -0.001(4) C1 0.054(7) 0.021(5) 0.036(5) -0.005(4) 0.012(5) 0.000(5) C2 0.036(6) 0.028(6) 0.049(6) -0.010(4) 0.012(5) -0.001(4) C3 0.055(7) 0.027(6) 0.037(5) -0.004(4) -0.002(5) -0.006(5) C4 0.048(7) 0.028(6) 0.040(5) -0.004(4) 0.007(5) -0.002(5) C5 0.069(8) 0.020(5) 0.039(5) 0.003(4) 0.012(5) 0.000(5) N11 0.048(6) 0.043(5) 0.031(4) -0.005(3) 0.010(4) -0.005(4) N12 0.042(5) 0.031(5) 0.043(5) 0.001(3) 0.009(4) 0.000(4) C11 0.062(7) 0.027(6) 0.030(5) -0.004(4) 0.011(5) 0.014(5) C12 0.064(8) 0.033(6) 0.036(5) -0.001(4) 0.016(5) 0.009(5) C13 0.058(8) 0.040(7) 0.036(5) -0.008(4) 0.010(5) -0.001(6) C14 0.079(9) 0.039(7) 0.048(6) -0.006(5) 0.014(6) 0.008(6) C15 0.110(12) 0.068(10) 0.040(6) 0.002(6) 0.013(7) 0.021(9) C16 0.113(12) 0.055(8) 0.051(7) 0.004(6) 0.039(8) 0.015(8) C17 0.074(9) 0.039(7) 0.056(7) 0.003(5) 0.018(6) 0.014(6) C18 0.047(7) 0.045(7) 0.058(6) -0.010(5) 0.006(5) -0.009(6) N21 0.046(5) 0.025(4) 0.028(4) -0.007(3) 0.004(4) -0.011(4) N22 0.047(6) 0.040(5) 0.030(4) -0.001(3) 0.008(4) -0.005(4) C21 0.051(7) 0.031(6) 0.023(4) 0.003(4) -0.005(4) 0.000(5) C22 0.037(6) 0.046(7) 0.028(5) -0.004(4) -0.001(4) 0.001(5) C23 0.035(6) 0.038(6) 0.039(5) 0.001(4) 0.001(5) 0.002(5) C24 0.034(6) 0.059(7) 0.052(6) -0.007(5) 0.003(5) -0.007(5) C25 0.057(8) 0.077(9) 0.041(6) -0.014(6) -0.005(6) -0.026(7) C26 0.060(8) 0.069(9) 0.039(6) -0.009(5) 0.003(6) 0.007(7) C27 0.061(8) 0.047(7) 0.043(6) -0.014(5) 0.011(5) -0.013(6) C28 0.054(8) 0.076(9) 0.042(6) -0.012(6) 0.010(5) -0.011(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 Hg1 N21 2.270(8) 2_545 ? Hg1 N1 2.525(8) . ? Hg1 I1 2.6652(10) . ? Hg1 I2 2.6948(12) . ? N1 C1 1.332(11) . ? N1 C5 1.345(11) . ? C1 C2 1.405(13) . ? C2 C3 1.383(13) . ? C2 C11 1.495(14) . ? C3 C4 1.404(14) . ? C4 C5 1.372(13) . ? C4 C21 1.476(13) . ? N11 C11 1.324(13) . ? N11 C13 1.383(13) . ? N12 C11 1.327(13) . ? N12 C12 1.371(12) . ? N12 C18 1.457(12) . ? C12 C13 1.388(14) . ? C12 C17 1.401(15) . ? C13 C14 1.399(14) . ? C14 C15 1.372(17) . ? C15 C16 1.377(18) . ? C16 C17 1.362(15) . ? N21 C21 1.333(12) . ? N21 C22 1.400(11) . ? N21 Hg1 2.270(8) 2 ? N22 C21 1.373(13) . ? N22 C23 1.378(11) . ? N22 C28 1.447(13) . ? C22 C23 1.369(13) . ? C22 C27 1.406(13) . ? C23 C24 1.394(14) . ? C24 C25 1.360(15) . ? C25 C26 1.384(17) . ? C26 C27 1.370(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 N21 Hg1 N1 93.1(3) 2_545 . ? N21 Hg1 I1 119.83(17) 2_545 . ? N1 Hg1 I1 100.64(18) . . ? N21 Hg1 I2 114.95(18) 2_545 . ? N1 Hg1 I2 97.39(17) . . ? I1 Hg1 I2 120.66(4) . . ? C1 N1 C5 118.3(8) . . ? C1 N1 Hg1 117.6(6) . . ? C5 N1 Hg1 123.4(6) . . ? N1 C1 C2 123.0(9) . . ? C3 C2 C1 118.2(9) . . ? C3 C2 C11 123.4(9) . . ? C1 C2 C11 118.4(8) . . ? C2 C3 C4 118.4(9) . . ? C5 C4 C3 119.4(9) . . ? C5 C4 C21 121.1(9) . . ? C3 C4 C21 119.5(9) . . ? N1 C5 C4 122.6(9) . . ? C11 N11 C13 103.7(9) . . ? C11 N12 C12 106.7(8) . . ? C11 N12 C18 128.6(8) . . ? C12 N12 C18 124.7(9) . . ? N11 C11 N12 114.2(8) . . ? N11 C11 C2 120.5(10) . . ? N12 C11 C2 125.3(9) . . ? N12 C12 C13 105.8(9) . . ? N12 C12 C17 133.0(11) . . ? C13 C12 C17 121.2(10) . . ? N11 C13 C12 109.7(8) . . ? N11 C13 C14 131.0(11) . . ? C12 C13 C14 119.3(10) . . ? C15 C14 C13 119.3(12) . . ? C14 C15 C16 120.3(11) . . ? C17 C16 C15 122.3(12) . . ? C16 C17 C12 117.6(12) . . ? C21 N21 C22 105.7(8) . . ? C21 N21 Hg1 129.2(6) . 2 ? C22 N21 Hg1 123.0(6) . 2 ? C21 N22 C23 107.1(8) . . ? C21 N22 C28 128.3(8) . . ? C23 N22 C28 124.5(9) . . ? N21 C21 N22 111.0(8) . . ? N21 C21 C4 126.9(9) . . ? N22 C21 C4 122.0(9) . . ? C23 C22 N21 109.3(8) . . ? C23 C22 C27 121.1(9) . . ? N21 C22 C27 129.6(9) . . ? C22 C23 N22 106.8(8) . . ? C22 C23 C24 121.9(9) . . ? N22 C23 C24 131.1(10) . . ? C25 C24 C23 116.4(10) . . ? C24 C25 C26 122.3(10) . . ? C27 C26 C25 121.9(10) . . ? C26 C27 C22 116.2(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.420 _refine_diff_density_min -1.559 _refine_diff_density_rms 0.195 _database_code_depnum_ccdc_archive 'CCDC 952911' ####################################################################### # # 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_5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 Cd I2 N5 O2' _chemical_formula_weight 741.63 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' Cd Cd -0.8075 1.2024 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.338(14) _cell_length_b 10.672(14) _cell_length_c 11.641(16) _cell_angle_alpha 69.36(4) _cell_angle_beta 86.54(4) _cell_angle_gamma 78.69(4) _cell_volume 1178(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.090 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 3.574 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.658 _exptl_absorpt_correction_T_max 0.699 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12261 _diffrn_reflns_av_R_equivalents 0.6041 _diffrn_reflns_av_sigmaI/netI 0.5397 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3995 _reflns_number_gt 944 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1000P)^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 3995 _refine_ls_number_parameters 219 _refine_ls_number_restraints 100 _refine_ls_R_factor_all 0.3896 _refine_ls_R_factor_gt 0.1411 _refine_ls_wR_factor_ref 0.3272 _refine_ls_wR_factor_gt 0.2649 _refine_ls_goodness_of_fit_ref 0.777 _refine_ls_restrained_S_all 0.779 _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 Cd1 Cd 0.1958(2) 0.7018(3) 0.7758(3) 0.0668(10) Uani 1 1 d . . . I1 I 0.4608(2) 0.6661(3) 0.7679(3) 0.0848(11) Uani 1 1 d . . . I2 I 0.0488(2) 0.9108(3) 0.8332(3) 0.0745(10) Uani 1 1 d . . . N1 N 0.185(2) 0.534(3) 0.972(2) 0.052(6) Uani 1 1 d U . . C1 C 0.254(3) 0.394(3) 0.993(3) 0.049(7) Uani 1 1 d U . . H1 H 0.3171 0.3756 0.9374 0.059 Uiso 1 1 calc R . . C2 C 0.225(2) 0.293(3) 1.091(3) 0.034(5) Uani 1 1 d U . . C3 C 0.148(3) 0.324(3) 1.180(3) 0.042(7) Uani 1 1 d U . . H3 H 0.1322 0.2542 1.2517 0.050 Uiso 1 1 calc R . . C4 C 0.091(3) 0.461(3) 1.163(3) 0.045(7) Uani 1 1 d U . . C5 C 0.118(3) 0.551(4) 1.064(3) 0.050(7) Uani 1 1 d U . . H5 H 0.0849 0.6405 1.0568 0.060 Uiso 1 1 calc R . . N11 N 0.297(2) 0.1058(17) 1.0168(15) 0.061(7) Uani 1 1 d DU . . N12 N 0.3238(19) 0.0723(17) 1.2104(19) 0.044(5) Uani 1 1 d DU . . C11 C 0.286(3) 0.159(2) 1.1083(19) 0.046(6) Uani 1 1 d DU . . C12 C 0.3474(9) -0.0287(10) 1.0654(10) 0.050(6) Uani 1 1 d GDU . . C13 C 0.3664(8) -0.0507(9) 1.1887(10) 0.103(15) Uani 1 1 d GDU . . C14 C 0.4179(10) -0.1806(9) 1.2686(11) 0.062(8) Uani 1 1 d GDU . . H14 H 0.4306 -0.1953 1.3511 0.074 Uiso 1 1 calc R . . C15 C 0.4504(11) -0.2885(9) 1.2252(13) 0.073(10) Uani 1 1 d GDU . . H15 H 0.4849 -0.3754 1.2787 0.088 Uiso 1 1 calc R . . C16 C 0.4314(11) -0.2665(10) 1.1019(13) 0.043(6) Uani 1 1 d GDU . . H16 H 0.4532 -0.3387 1.0729 0.052 Uiso 1 1 calc R . . C17 C 0.3799(10) -0.1366(11) 1.0220(12) 0.045(6) Uani 1 1 d GDU . . H17 H 0.3672 -0.1219 0.9395 0.054 Uiso 1 1 calc R . . C18 C 0.2576(12) 0.1625(12) 0.8943(9) 0.078(11) Uani 1 1 d GDU . . H18A H 0.2235 0.2581 0.8741 0.117 Uiso 1 1 calc R . . H18B H 0.1903 0.1186 0.8806 0.117 Uiso 1 1 calc R . . H18C H 0.3320 0.1498 0.8434 0.117 Uiso 1 1 calc R . . N21 N 0.0109(9) 0.5953(8) 1.2904(10) 0.056(8) Uani 1 1 d GDU . . N22 N -0.0972(7) 0.4322(8) 1.2943(8) 0.044(6) Uani 1 1 d GDU . . C21 C -0.0022(8) 0.4913(8) 1.2513(8) 0.046(8) Uani 1 1 d GDU . . C22 C -0.0956(9) 0.6014(9) 1.3693(9) 0.037(6) Uani 1 1 d GDU . . C23 C -0.1597(8) 0.4969(9) 1.3772(9) 0.036(6) Uani 1 1 d GDU . . C24 C -0.2760(9) 0.4838(11) 1.4272(11) 0.091(15) Uani 1 1 d GDU . . H24 H -0.3222 0.4213 1.4181 0.109 Uiso 1 1 calc R . . C25 C -0.3268(11) 0.5664(11) 1.4938(12) 0.072(10) Uani 1 1 d GDU . . H25 H -0.4072 0.5567 1.5330 0.087 Uiso 1 1 calc R . . C26 C -0.2581(12) 0.6678(11) 1.5041(11) 0.098(14) Uani 1 1 d GDU . . H26 H -0.2895 0.7198 1.5529 0.118 Uiso 1 1 calc R . . C27 C -0.1510(11) 0.6821(10) 1.4419(11) 0.061(9) Uani 1 1 d GDU . . H27 H -0.1070 0.7492 1.4444 0.074 Uiso 1 1 calc R . . C28 C 0.1068(10) 0.6827(9) 1.2615(13) 0.074(13) Uani 1 1 d GDU . . H28A H 0.0867 0.7452 1.3053 0.111 Uiso 1 1 calc R . . H28B H 0.1046 0.7328 1.1749 0.111 Uiso 1 1 calc R . . H28C H 0.1931 0.6284 1.2851 0.111 Uiso 1 1 calc R . . O2W O 0.154(3) 0.8421(14) 0.5445(11) 0.195(18) Uiso 1 1 d G . . O1W O 0.3174(11) 0.0302(11) 1.4637(9) 0.202(19) Uiso 1 1 d G . . 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 Cd1 0.0628(17) 0.0558(18) 0.091(2) -0.0382(18) 0.0125(15) -0.0132(14) I1 0.0669(16) 0.092(2) 0.120(3) -0.066(2) 0.0260(16) -0.0238(15) I2 0.0626(15) 0.0533(17) 0.117(2) -0.0433(17) 0.0056(15) -0.0096(13) N1 0.061(16) 0.058(11) 0.034(14) -0.015(11) -0.009(11) -0.002(13) C1 0.031(15) 0.050(11) 0.08(2) -0.027(12) 0.027(15) -0.035(12) C2 0.035(14) 0.048(9) 0.032(15) -0.022(9) -0.016(10) -0.017(10) C3 0.045(17) 0.045(12) 0.039(17) -0.012(12) 0.003(13) -0.020(13) C4 0.033(15) 0.049(14) 0.061(17) -0.023(12) 0.010(13) -0.024(13) C5 0.040(18) 0.051(15) 0.048(19) -0.008(12) -0.004(14) 0.003(15) N11 0.047(14) 0.057(12) 0.077(13) -0.040(11) -0.040(15) 0.033(13) N12 0.020(12) 0.045(11) 0.069(13) -0.013(10) -0.007(12) -0.023(10) C11 0.054(18) 0.047(9) 0.049(14) -0.021(9) 0.011(15) -0.031(13) C12 0.039(17) 0.038(11) 0.066(13) -0.008(10) 0.011(15) -0.014(13) C13 0.15(4) 0.071(14) 0.050(14) -0.015(12) 0.04(2) 0.05(2) C14 0.10(3) 0.037(11) 0.045(15) -0.003(10) 0.038(16) -0.043(15) C15 0.07(2) 0.060(16) 0.074(18) -0.020(16) -0.03(2) 0.03(2) C16 0.034(16) 0.029(11) 0.067(17) -0.010(13) -0.008(15) -0.016(12) C17 0.027(15) 0.035(12) 0.062(17) -0.004(11) 0.006(14) -0.003(13) C18 0.08(2) 0.08(2) 0.059(16) -0.038(16) -0.03(2) 0.05(2) N21 0.030(12) 0.048(17) 0.10(2) -0.043(16) 0.003(11) -0.005(10) N22 0.058(14) 0.036(15) 0.029(15) 0.005(12) 0.014(10) -0.023(11) C21 0.052(16) 0.022(16) 0.063(19) -0.011(14) 0.012(13) -0.017(11) C22 0.029(13) 0.047(18) 0.025(18) 0.000(14) -0.019(10) -0.003(11) C23 0.022(12) 0.040(17) 0.037(19) -0.006(15) -0.016(10) 0.005(11) C24 0.11(3) 0.13(4) 0.06(3) -0.05(3) 0.07(2) -0.09(3) C25 0.049(17) 0.05(2) 0.07(3) 0.009(19) -0.003(16) 0.048(13) C26 0.17(4) 0.06(3) 0.05(3) -0.02(2) 0.04(2) 0.00(2) C27 0.08(2) 0.05(2) 0.05(2) -0.024(19) -0.030(14) 0.019(16) C28 0.052(19) 0.06(2) 0.14(4) -0.08(3) 0.04(2) -0.024(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 Cd1 N22 2.29(2) 2_567 ? Cd1 N1 2.37(3) . ? Cd1 O2W 2.593(14) . ? Cd1 I1 2.691(5) . ? Cd1 I2 2.707(4) . ? N1 C5 1.28(3) . ? N1 C1 1.47(4) . ? C1 C2 1.33(4) . ? C2 C3 1.36(3) . ? C2 C11 1.40(3) . ? C3 C4 1.42(4) . ? C4 C5 1.27(4) . ? C4 C21 1.44(3) . ? N11 C12 1.351(14) . ? N11 C11 1.363(16) . ? N11 C18 1.389(14) . ? N12 C11 1.250(17) . ? N12 C13 1.405(14) . ? C12 C13 1.3900 . ? C12 C17 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C16 C17 1.3900 . ? N21 C21 1.3714 . ? N21 C22 1.3971 . ? N21 C28 1.4379 . ? N22 C21 1.2547 . ? N22 C23 1.4313 . ? N22 Cd1 2.289(9) 2_567 ? C22 C23 1.3778 . ? C22 C27 1.4297 . ? C23 C24 1.3148 . ? C24 C25 1.3807 . ? C25 C26 1.4456 . ? C26 C27 1.2912 . ? 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 N22 Cd1 N1 85.6(6) 2_567 . ? N22 Cd1 O2W 76.0(7) 2_567 . ? N1 Cd1 O2W 161.0(9) . . ? N22 Cd1 I1 117.4(4) 2_567 . ? N1 Cd1 I1 95.9(6) . . ? O2W Cd1 I1 96.7(6) . . ? N22 Cd1 I2 120.5(4) 2_567 . ? N1 Cd1 I2 95.7(6) . . ? O2W Cd1 I2 89.7(4) . . ? I1 Cd1 I2 121.48(12) . . ? C5 N1 C1 115(3) . . ? C5 N1 Cd1 127(2) . . ? C1 N1 Cd1 118.5(18) . . ? C2 C1 N1 119(2) . . ? C1 C2 C3 120(3) . . ? C1 C2 C11 119(2) . . ? C3 C2 C11 121(3) . . ? C4 C3 C2 120(3) . . ? C5 C4 C3 117(3) . . ? C5 C4 C21 123(3) . . ? C3 C4 C21 120(3) . . ? C4 C5 N1 129(3) . . ? C12 N11 C11 108.3(12) . . ? C12 N11 C18 119.6(11) . . ? C11 N11 C18 131.9(14) . . ? C11 N12 C13 105.4(15) . . ? N12 C11 N11 113.1(17) . . ? N12 C11 C2 123.7(19) . . ? N11 C11 C2 123(2) . . ? N11 C12 C13 103.9(6) . . ? N11 C12 C17 136.1(6) . . ? C13 C12 C17 120.0 . . ? C14 C13 C12 120.0 . . ? C14 C13 N12 130.6(9) . . ? C12 C13 N12 109.4(9) . . ? C13 C14 C15 120.0 . . ? C16 C15 C14 120.0 . . ? C15 C16 C17 120.0 . . ? C16 C17 C12 120.0 . . ? C21 N21 C22 103.6 . . ? C21 N21 C28 131.2 . . ? C22 N21 C28 125.2 . . ? C21 N22 C23 104.8 . . ? C21 N22 Cd1 129.9(3) . 2_567 ? C23 N22 Cd1 123.1(2) . 2_567 ? N22 C21 N21 116.3 . . ? N22 C21 C4 125.5(11) . . ? N21 C21 C4 118.1(11) . . ? C23 C22 N21 107.3 . . ? C23 C22 C27 114.9 . . ? N21 C22 C27 137.8 . . ? C24 C23 C22 124.4 . . ? C24 C23 N22 125.7 . . ? C22 C23 N22 107.8 . . ? C23 C24 C25 117.3 . . ? C24 C25 C26 121.6 . . ? C27 C26 C25 116.3 . . ? C26 C27 C22 124.2 . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.967 _refine_diff_density_min -2.078 _refine_diff_density_rms 0.239 _database_code_depnum_ccdc_archive 'CCDC 952912' ####################################################################### # # 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_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H42 Cl6 Cu3 N10 O4' _chemical_formula_weight 1154.18 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' Cu Cu 0.3201 1.2651 '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 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 14.449(3) _cell_length_b 8.2156(14) _cell_length_c 20.383(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.156(5) _cell_angle_gamma 90.00 _cell_volume 2285.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1170 _exptl_absorpt_coefficient_mu 1.789 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.706 _exptl_absorpt_correction_T_max 0.765 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20912 _diffrn_reflns_av_R_equivalents 0.1585 _diffrn_reflns_av_sigmaI/netI 0.0924 _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 -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 22.49 _reflns_number_total 2983 _reflns_number_gt 1839 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1000P)^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 2983 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1193 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1834 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.009 _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 Cu1 Cu 0.76925(8) -0.32066(14) 0.12883(6) 0.0269(4) Uani 1 1 d . . . Cu2 Cu 1.0000 0.0000 0.0000 0.0339(5) Uani 1 2 d S . . Cl1 Cl 0.73101(19) -0.3868(3) 0.22264(13) 0.0416(7) Uani 1 1 d . . . Cl2 Cl 0.7497(2) -0.3965(3) 0.01951(14) 0.0505(8) Uani 1 1 d . . . Cl3 Cl 1.1401(2) 0.0284(5) 0.08935(17) 0.0764(12) Uani 1 1 d . . . N1 N 0.9233(5) 0.0985(9) 0.0601(4) 0.0258(19) Uani 1 1 d . . . C1 C 0.9596(6) 0.2333(12) 0.0968(5) 0.029(2) Uani 1 1 d . . . H1 H 1.0188 0.2756 0.0956 0.035 Uiso 1 1 calc R . . C2 C 0.9112(6) 0.3105(11) 0.1361(5) 0.023(2) Uani 1 1 d . . . C3 C 0.8246(6) 0.2459(11) 0.1404(5) 0.024(2) Uani 1 1 d . . . H3 H 0.7924 0.2944 0.1681 0.029 Uiso 1 1 calc R . . C4 C 0.7873(6) 0.1064(11) 0.1021(5) 0.023(2) Uani 1 1 d . . . C5 C 0.8391(7) 0.0360(12) 0.0631(5) 0.028(2) Uani 1 1 d . . . H5 H 0.8146 -0.0581 0.0380 0.034 Uiso 1 1 calc R . . N11 N 1.0485(5) 0.4733(9) 0.2165(4) 0.0256(19) Uani 1 1 d . . . N12 N 0.9067(5) 0.5974(10) 0.1736(4) 0.029(2) Uani 1 1 d . . . C11 C 0.9555(6) 0.4620(11) 0.1757(5) 0.022(2) Uani 1 1 d . . . C12 C 0.9721(7) 0.7048(11) 0.2179(5) 0.026(2) Uani 1 1 d . . . C13 C 1.0615(7) 0.6288(12) 0.2438(5) 0.030(2) Uani 1 1 d . . . C14 C 1.1421(8) 0.7046(15) 0.2898(5) 0.044(3) Uani 1 1 d . . . H14 H 1.2021 0.6516 0.3074 0.053 Uiso 1 1 calc R . . C15 C 1.1297(8) 0.8621(15) 0.3083(6) 0.051(3) Uani 1 1 d . . . H15 H 1.1823 0.9186 0.3384 0.061 Uiso 1 1 calc R . . C16 C 1.0371(8) 0.9383(13) 0.2817(5) 0.043(3) Uani 1 1 d . . . H16 H 1.0303 1.0446 0.2950 0.051 Uiso 1 1 calc R . . C17 C 0.9582(8) 0.8627(11) 0.2377(5) 0.035(3) Uani 1 1 d . . . H17 H 0.8974 0.9136 0.2213 0.042 Uiso 1 1 calc R . . C18 C 1.1261(8) 0.3471(13) 0.2361(6) 0.052(3) Uani 1 1 d . . . H18A H 1.1858 0.3941 0.2662 0.078 Uiso 1 1 calc R . . H18B H 1.1365 0.3057 0.1951 0.078 Uiso 1 1 calc R . . H18C H 1.1062 0.2599 0.2599 0.078 Uiso 1 1 calc R . . N21 N 0.6130(5) 0.1191(9) 0.0954(4) 0.0251(19) Uani 1 1 d . . . N22 N 0.6777(5) -0.1284(9) 0.1032(4) 0.0258(19) Uani 1 1 d . . . C21 C 0.6944(6) 0.0305(11) 0.1018(5) 0.023(2) Uani 1 1 d . . . C22 C 0.5790(6) -0.1447(12) 0.0947(5) 0.027(2) Uani 1 1 d . . . C23 C 0.5382(7) 0.0094(12) 0.0913(5) 0.026(2) Uani 1 1 d . . . C24 C 0.4396(7) 0.0334(13) 0.0826(5) 0.031(3) Uani 1 1 d . . . H24 H 0.4130 0.1372 0.0801 0.038 Uiso 1 1 calc R . . C25 C 0.3836(7) -0.1032(15) 0.0781(5) 0.040(3) Uani 1 1 d . . . H25 H 0.3174 -0.0916 0.0726 0.048 Uiso 1 1 calc R . . C26 C 0.4226(7) -0.2579(14) 0.0814(5) 0.042(3) Uani 1 1 d . . . H26 H 0.3819 -0.3477 0.0773 0.050 Uiso 1 1 calc R . . C27 C 0.5220(7) -0.2822(13) 0.0909(5) 0.036(3) Uani 1 1 d . . . H27 H 0.5486 -0.3862 0.0944 0.043 Uiso 1 1 calc R . . C28 C 0.6025(8) 0.2976(12) 0.0934(5) 0.041(3) Uani 1 1 d . . . H28A H 0.5360 0.3258 0.0885 0.061 Uiso 1 1 calc R . . H28B H 0.6189 0.3400 0.0548 0.061 Uiso 1 1 calc R . . H28C H 0.6457 0.3432 0.1358 0.061 Uiso 1 1 calc R . . O1W O 0.9894(14) -0.284(2) 0.0380(10) 0.215(8) Uiso 1 1 d . . . O2W O 1.1235(15) -0.413(3) 0.0817(11) 0.239(9) 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 Cu1 0.0250(7) 0.0232(7) 0.0337(7) -0.0005(6) 0.0113(5) 0.0026(6) Cu2 0.0213(10) 0.0434(13) 0.0400(11) -0.0172(9) 0.0140(8) -0.0027(9) Cl1 0.0469(17) 0.0437(18) 0.0414(16) 0.0034(13) 0.0241(13) 0.0027(14) Cl2 0.074(2) 0.0404(18) 0.0386(16) -0.0062(14) 0.0198(15) 0.0020(16) Cl3 0.0287(16) 0.126(3) 0.067(2) -0.051(2) 0.0051(15) 0.0109(19) N1 0.014(4) 0.028(5) 0.039(5) -0.011(4) 0.014(4) 0.003(4) C1 0.018(5) 0.035(7) 0.036(6) -0.007(5) 0.010(5) -0.009(5) C2 0.020(5) 0.017(6) 0.034(5) -0.001(4) 0.009(4) 0.004(4) C3 0.019(5) 0.024(6) 0.036(6) -0.005(5) 0.017(5) 0.002(5) C4 0.015(5) 0.012(5) 0.046(6) 0.004(5) 0.015(5) -0.003(4) C5 0.025(6) 0.030(6) 0.031(6) -0.003(5) 0.011(5) -0.001(5) N11 0.014(4) 0.023(5) 0.038(5) -0.001(4) 0.007(4) 0.005(4) N12 0.023(5) 0.028(5) 0.034(5) -0.009(4) 0.008(4) -0.003(4) C11 0.018(5) 0.020(6) 0.031(6) 0.003(4) 0.011(5) 0.001(5) C12 0.027(6) 0.023(6) 0.024(5) -0.004(5) 0.002(4) -0.004(5) C13 0.030(6) 0.029(7) 0.026(5) -0.003(5) 0.002(5) -0.003(5) C14 0.036(7) 0.053(9) 0.038(7) -0.003(6) 0.006(6) -0.010(6) C15 0.039(7) 0.055(9) 0.046(7) -0.017(6) -0.002(6) -0.029(7) C16 0.062(8) 0.023(7) 0.041(7) -0.017(5) 0.015(6) -0.009(6) C17 0.043(7) 0.018(6) 0.042(6) -0.003(5) 0.013(6) 0.001(5) C18 0.044(7) 0.042(8) 0.074(9) -0.005(6) 0.026(7) 0.004(6) N21 0.024(5) 0.010(4) 0.041(5) -0.005(4) 0.010(4) 0.000(4) N22 0.018(5) 0.025(5) 0.035(5) -0.002(4) 0.011(4) 0.002(4) C21 0.021(5) 0.014(6) 0.034(6) -0.002(4) 0.010(4) -0.007(5) C22 0.018(6) 0.029(7) 0.034(6) -0.001(5) 0.007(5) 0.005(5) C23 0.022(6) 0.030(7) 0.028(6) 0.001(5) 0.010(4) -0.002(5) C24 0.028(6) 0.030(7) 0.043(6) 0.011(5) 0.022(5) 0.012(5) C25 0.023(6) 0.056(8) 0.041(7) 0.013(6) 0.009(5) 0.001(6) C26 0.029(7) 0.042(8) 0.050(7) 0.010(6) 0.007(5) -0.008(6) C27 0.028(6) 0.027(7) 0.047(7) 0.012(5) 0.006(5) -0.007(5) C28 0.044(7) 0.031(7) 0.052(7) -0.003(5) 0.022(6) -0.002(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 Cu1 N12 2.011(8) 1_545 ? Cu1 N22 2.016(7) . ? Cu1 Cl1 2.225(3) . ? Cu1 Cl2 2.241(3) . ? Cu2 N1 2.068(7) 3_755 ? Cu2 N1 2.068(7) . ? Cu2 Cl3 2.247(3) . ? Cu2 Cl3 2.247(3) 3_755 ? N1 C5 1.340(11) . ? N1 C1 1.343(11) . ? C1 C2 1.380(12) . ? C2 C3 1.388(12) . ? C2 C11 1.507(13) . ? C3 C4 1.392(12) . ? C4 C5 1.384(12) . ? C4 C21 1.479(12) . ? N11 C11 1.331(11) . ? N11 C13 1.382(12) . ? N11 C18 1.483(12) . ? N12 C11 1.310(11) . ? N12 C12 1.388(11) . ? N12 Cu1 2.011(8) 1_565 ? C12 C13 1.375(13) . ? C12 C17 1.392(13) . ? C13 C14 1.381(13) . ? C14 C15 1.376(15) . ? C15 C16 1.414(15) . ? C16 C17 1.348(13) . ? N21 C21 1.353(11) . ? N21 C23 1.388(11) . ? N21 C28 1.474(12) . ? N22 C21 1.329(11) . ? N22 C22 1.386(11) . ? C22 C27 1.385(13) . ? C22 C23 1.389(13) . ? C23 C24 1.390(12) . ? C24 C25 1.369(14) . ? C25 C26 1.383(15) . ? C26 C27 1.399(13) . ? 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 N12 Cu1 N22 147.8(3) 1_545 . ? N12 Cu1 Cl1 90.9(2) 1_545 . ? N22 Cu1 Cl1 95.0(2) . . ? N12 Cu1 Cl2 98.1(2) 1_545 . ? N22 Cu1 Cl2 95.9(2) . . ? Cl1 Cu1 Cl2 143.22(12) . . ? N1 Cu2 N1 180.0(3) 3_755 . ? N1 Cu2 Cl3 90.3(2) 3_755 . ? N1 Cu2 Cl3 89.7(2) . . ? N1 Cu2 Cl3 89.7(2) 3_755 3_755 ? N1 Cu2 Cl3 90.3(2) . 3_755 ? Cl3 Cu2 Cl3 180.0(2) . 3_755 ? C5 N1 C1 119.1(8) . . ? C5 N1 Cu2 123.2(6) . . ? C1 N1 Cu2 117.7(6) . . ? N1 C1 C2 121.5(8) . . ? C1 C2 C3 120.0(9) . . ? C1 C2 C11 118.9(8) . . ? C3 C2 C11 121.1(8) . . ? C2 C3 C4 118.1(8) . . ? C5 C4 C3 118.9(8) . . ? C5 C4 C21 118.9(8) . . ? C3 C4 C21 122.2(8) . . ? N1 C5 C4 122.4(9) . . ? C11 N11 C13 107.0(8) . . ? C11 N11 C18 129.7(8) . . ? C13 N11 C18 123.1(8) . . ? C11 N12 C12 106.0(8) . . ? C11 N12 Cu1 137.7(6) . 1_565 ? C12 N12 Cu1 116.2(6) . 1_565 ? N12 C11 N11 112.5(8) . . ? N12 C11 C2 123.7(8) . . ? N11 C11 C2 123.8(8) . . ? C13 C12 N12 108.3(8) . . ? C13 C12 C17 121.2(9) . . ? N12 C12 C17 130.5(9) . . ? C12 C13 C14 122.2(10) . . ? C12 C13 N11 106.2(8) . . ? C14 C13 N11 131.6(10) . . ? C15 C14 C13 116.9(10) . . ? C14 C15 C16 120.2(10) . . ? C17 C16 C15 122.6(10) . . ? C16 C17 C12 116.8(10) . . ? C21 N21 C23 107.0(7) . . ? C21 N21 C28 128.0(8) . . ? C23 N21 C28 125.0(8) . . ? C21 N22 C22 106.2(8) . . ? C21 N22 Cu1 131.8(6) . . ? C22 N22 Cu1 121.2(6) . . ? N22 C21 N21 111.8(7) . . ? N22 C21 C4 125.8(8) . . ? N21 C21 C4 122.2(8) . . ? C27 C22 N22 130.8(9) . . ? C27 C22 C23 120.4(8) . . ? N22 C22 C23 108.7(8) . . ? N21 C23 C22 106.2(8) . . ? N21 C23 C24 131.3(9) . . ? C22 C23 C24 122.4(9) . . ? C25 C24 C23 116.8(9) . . ? C24 C25 C26 121.8(9) . . ? C25 C26 C27 121.4(10) . . ? C22 C27 C26 117.1(10) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 22.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.273 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.120 _database_code_depnum_ccdc_archive 'CCDC 952913'