# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_a _database_code_depnum_ccdc_archive 'CCDC 894323' #TrackingRef 'DMF-check.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 N7 O2 Zn, C3 H7 N O' _chemical_formula_sum 'C14 H16 N8 O3 Zn' _chemical_formula_weight 409.72 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 18.2266(6) _cell_length_b 10.3496(4) _cell_length_c 9.1663(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1729.11(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1934 _cell_measurement_theta_min 2.2584 _cell_measurement_theta_max 28.9007 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.574 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 1.433 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6983 _exptl_absorpt_correction_T_max 0.7927 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 0.029 273.9 105.9 2 0.500 0.500 -0.001 273.8 105.8 _platon_squeeze_details ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2083 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4169 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2677 _reflns_number_gt 2264 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _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^)+(0.0515P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 2677 _refine_ls_number_parameters 190 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 Zn1 Zn 0.09975(2) 0.52837(5) 0.87822(10) 0.02446(16) Uani 1 1 d . . . C1 C 0.0419(3) 0.3450(5) 1.2758(6) 0.0261(12) Uani 1 1 d . . . C2 C 0.0892(3) 0.3515(5) 1.1601(6) 0.0285(12) Uani 1 1 d . . . C3 C 0.1515(3) 0.2671(5) 1.1593(6) 0.0318(13) Uani 1 1 d . . . C4 C 0.1086(3) 0.1956(5) 1.3841(9) 0.0463(14) Uani 1 1 d . . . H4A H 0.1160 0.1395 1.4620 0.056 Uiso 1 1 calc R . . C5 C 0.0023(5) 0.4861(8) 1.1231(9) 0.0330(14) Uani 1 1 d . . . H5A H -0.0265 0.5506 1.0815 0.040 Uiso 1 1 calc R . . C6 C 0.1712(3) 0.7892(6) 0.9035(6) 0.0378(15) Uani 1 1 d . . . C7 C 0.2162(3) 0.8799(5) 0.9711(6) 0.0383(14) Uani 1 1 d . . . H7A H 0.2184 0.9638 0.9349 0.046 Uiso 1 1 calc R . . C8 C 0.2574(3) 0.8466(5) 1.0904(6) 0.0308(13) Uani 1 1 d . . . C9 C 0.2536(3) 0.7206(6) 1.1420(7) 0.0387(14) Uani 1 1 d . . . H9A H 0.2809 0.6947 1.2225 0.046 Uiso 1 1 calc R . . C10 C 0.2085(3) 0.6355(6) 1.0709(6) 0.0392(15) Uani 1 1 d . . . H10A H 0.2067 0.5507 1.1040 0.047 Uiso 1 1 calc R . . C11 C 0.3073(3) 0.9423(5) 1.1616(6) 0.0323(13) Uani 1 1 d . . . O1 O 0.3186(2) 1.0498(4) 1.1100(4) 0.0390(10) Uani 1 1 d . . . O2 O 0.33672(19) 0.9027(4) 1.2834(4) 0.0394(10) Uani 1 1 d . . . N1 N -0.0143(2) 0.4295(4) 1.2531(4) 0.0296(10) Uani 1 1 d . . . N2 N 0.0629(2) 0.4415(4) 1.0608(4) 0.0267(10) Uani 1 1 d . . . N3 N 0.0502(2) 0.2688(4) 1.3943(6) 0.0382(11) Uani 1 1 d . . . N4 N 0.1588(3) 0.1895(5) 1.2793(5) 0.0457(13) Uani 1 1 d . . . N5 N 0.2006(3) 0.2587(5) 1.0532(6) 0.0516(14) Uani 1 1 d . . . H5B H 0.2364 0.2050 1.0603 0.062 Uiso 1 1 calc R . . H5C H 0.1966 0.3069 0.9772 0.062 Uiso 1 1 calc R . . N6 N 0.1668(2) 0.6677(4) 0.9563(5) 0.0321(11) Uani 1 1 d . . . N7 N 0.1332(3) 0.8168(6) 0.7856(6) 0.0694(19) Uani 1 1 d . . . H7B H 0.1356 0.8928 0.7480 0.083 Uiso 1 1 calc R . . H7C H 0.1058 0.7588 0.7461 0.083 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 Zn1 0.0217(3) 0.0305(3) 0.0211(3) -0.0030(4) -0.0012(4) 0.0010(2) C1 0.021(2) 0.035(3) 0.023(3) -0.002(2) 0.001(2) 0.003(2) C2 0.025(3) 0.030(3) 0.031(3) -0.004(2) -0.010(3) -0.001(2) C3 0.024(3) 0.033(3) 0.038(3) 0.000(3) -0.001(3) 0.003(2) C4 0.056(3) 0.051(3) 0.031(3) 0.004(5) 0.012(4) 0.011(3) C5 0.028(2) 0.041(4) 0.030(3) 0.009(2) 0.004(2) 0.009(2) C6 0.037(3) 0.042(3) 0.034(4) 0.007(3) -0.011(3) -0.010(2) C7 0.043(3) 0.029(3) 0.042(3) 0.007(3) -0.010(3) -0.007(3) C8 0.025(3) 0.032(3) 0.035(3) -0.007(3) 0.002(3) -0.002(2) C9 0.038(3) 0.045(3) 0.033(3) 0.007(3) -0.017(3) -0.007(3) C10 0.048(4) 0.041(3) 0.028(3) 0.005(3) -0.012(3) -0.004(3) C11 0.030(3) 0.036(3) 0.032(3) -0.004(3) -0.003(3) -0.004(3) O1 0.035(2) 0.034(2) 0.047(3) -0.0020(19) -0.008(2) -0.0088(19) O2 0.038(2) 0.046(2) 0.035(2) -0.001(2) -0.0153(19) -0.008(2) N1 0.028(2) 0.041(3) 0.019(2) 0.002(2) -0.003(2) 0.004(2) N2 0.026(2) 0.032(2) 0.023(2) 0.0056(19) 0.004(2) 0.004(2) N3 0.036(2) 0.051(3) 0.027(3) 0.005(3) 0.000(3) 0.009(2) N4 0.048(3) 0.050(3) 0.039(3) 0.009(3) -0.001(3) 0.016(3) N5 0.043(3) 0.067(4) 0.045(3) 0.012(3) 0.011(3) 0.029(3) N6 0.032(2) 0.030(2) 0.034(3) 0.000(2) -0.013(2) -0.009(2) N7 0.080(4) 0.057(4) 0.071(4) 0.026(3) -0.047(4) -0.033(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.946(4) 4_544 ? Zn1 N1 1.982(4) 2_564 ? Zn1 N6 2.022(4) . ? Zn1 N2 2.015(4) . ? C1 N3 1.351(7) . ? C1 N1 1.363(6) . ? C1 C2 1.368(7) . ? C2 N2 1.388(7) . ? C2 C3 1.433(7) . ? C3 N5 1.324(7) . ? C3 N4 1.369(7) . ? C4 N4 1.329(8) . ? C4 N3 1.311(6) . ? C4 H4A 0.9300 . ? C5 N2 1.326(9) . ? C5 N1 1.362(9) . ? C5 H5A 0.9300 . ? C6 N7 1.315(7) . ? C6 C7 1.392(7) . ? C6 N6 1.350(7) . ? C7 C8 1.370(7) . ? C7 H7A 0.9300 . ? C8 C9 1.389(8) . ? C8 C11 1.495(7) . ? C9 C10 1.370(8) . ? C9 H9A 0.9300 . ? C10 N6 1.338(7) . ? C10 H10A 0.9300 . ? C11 O1 1.226(6) . ? C11 O2 1.305(7) . ? O2 Zn1 1.946(4) 4 ? N1 Zn1 1.982(4) 2_565 ? N5 H5B 0.8600 . ? N5 H5C 0.8600 . ? N7 H7B 0.8600 . ? N7 H7C 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 N1 110.86(17) 4_544 2_564 ? O2 Zn1 N6 105.97(17) 4_544 . ? N1 Zn1 N6 121.52(19) 2_564 . ? O2 Zn1 N2 105.74(17) 4_544 . ? N1 Zn1 N2 108.46(17) 2_564 . ? N6 Zn1 N2 103.05(18) . . ? N3 C1 N1 125.5(4) . . ? N3 C1 C2 125.6(5) . . ? N1 C1 C2 108.9(5) . . ? C1 C2 N2 108.8(5) . . ? C1 C2 C3 118.3(5) . . ? N2 C2 C3 132.9(5) . . ? N5 C3 N4 119.1(5) . . ? N5 C3 C2 125.4(5) . . ? N4 C3 C2 115.5(5) . . ? N4 C4 N3 129.7(7) . . ? N4 C4 H4A 115.2 . . ? N3 C4 H4A 115.2 . . ? N2 C5 N1 114.3(6) . . ? N2 C5 H5A 122.8 . . ? N1 C5 H5A 122.8 . . ? N7 C6 C7 122.0(6) . . ? N7 C6 N6 117.8(5) . . ? C7 C6 N6 120.2(5) . . ? C6 C7 C8 120.6(5) . . ? C6 C7 H7A 119.7 . . ? C8 C7 H7A 119.7 . . ? C7 C8 C9 118.7(5) . . ? C7 C8 C11 121.0(5) . . ? C9 C8 C11 120.2(5) . . ? C10 C9 C8 118.1(5) . . ? C10 C9 H9A 120.9 . . ? C8 C9 H9A 120.9 . . ? N6 C10 C9 123.7(5) . . ? N6 C10 H10A 118.2 . . ? C9 C10 H10A 118.2 . . ? O1 C11 O2 123.1(5) . . ? O1 C11 C8 122.4(5) . . ? O2 C11 C8 114.5(5) . . ? C11 O2 Zn1 114.6(4) . 4 ? C1 N1 C5 104.0(5) . . ? C1 N1 Zn1 130.1(3) . 2_565 ? C5 N1 Zn1 125.9(4) . 2_565 ? C5 N2 C2 103.9(5) . . ? C5 N2 Zn1 118.7(4) . . ? C2 N2 Zn1 136.7(3) . . ? C1 N3 C4 111.8(6) . . ? C4 N4 C3 119.1(5) . . ? C3 N5 H5B 120.0 . . ? C3 N5 H5C 120.0 . . ? H5B N5 H5C 120.0 . . ? C10 N6 C6 118.7(5) . . ? C10 N6 Zn1 116.3(4) . . ? C6 N6 Zn1 125.0(4) . . ? C6 N7 H7B 120.0 . . ? C6 N7 H7C 120.0 . . ? H7B N7 H7C 120.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.324 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.072