# Electronic Supplementary Material (ESI) for Metallomics # 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_Cu2CM _database_code_depnum_ccdc_archive 'CCDC 886726' #TrackingRef 'web_deposit_cif_file_0_TimStorr_1339781702.combined_Storr.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_sum 'C13 H17 Cl2 Cu1 N5 O1' _chemical_formula_moiety 'C13 H17 Cl2 Cu1 N5 O1' _chemical_formula_weight 393.76 #============================================================= # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 #------------------------------------------------ _cell_length_a 12.4564(3) _cell_length_b 8.7526(2) _cell_length_c 14.9349(4) _cell_angle_alpha 90 _cell_angle_beta 96.602(2) _cell_angle_gamma 90 _cell_volume 1617.49(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6445 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.07 _cell_measurement_temperature 296(2) _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_max 0.13 _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.688 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6252 _exptl_absorpt_correction_T_max 0.7456 #============================================================================= # 7. EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_method '\w/2\q ' _diffrn_ambient_temperature 296(2) _diffrn_reflns_number 13351 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_theta_min 2.018 _diffrn_reflns_theta_max 28.101 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.539 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 #========================================================================== # 8. REFINEMENT DATA # The values actually used during refinement # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _oxford_reflns_threshold_expression_ref I>2.5\s(I) _refine_ls_number_reflns 2516 _refine_ls_number_restraints 0 _refine_ls_number_parameters 223 _oxford_refine_ls_R_factor_ref 0.0444 _refine_ls_wR_factor_ref 0.0443 _refine_ls_goodness_of_fit_ref 1.1370 # The values computed from all data _oxford_reflns_number_all 3925 _refine_ls_R_factor_all 0.0685 _refine_ls_wR_factor_all 0.0925 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3065 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_gt 0.0501 _reflns_number_total 3925 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.262 0.294 0.103 ; _refine_ls_shift/su_max 0.000447 _refine_diff_density_min -0.33 _refine_diff_density_max 0.73 _reflns_limit_h_min -16 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_refine_ls_scale 0.07530(15) _oxford_diffrn_Wilson_B_factor 2.93 _oxford_diffrn_Wilson_scale 183.01 # Number of reflections with Friedels Law is 3925 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3935 #--------------------------------------------------------- _chemical_name_systematic ; ; # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr # none if no extinction, _refine_ls_extinction_method None #========================================================== # 9. General computing _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_structure_solution ; SIR92 (Altomare et al, 1994) CRYSTALS (Watkin, 1988) ; #=================================================================== # 10. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' #============================================================================== # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # TODO check _oxford_atom_site_special_shape 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.87159(3) 0.11657(4) 0.51145(3) 0.0383 1.0000 Uani . . . . . . . Cl1 Cl 0.93608(7) -0.09860(8) 0.58273(6) 0.0431 1.0000 Uani . . . . . . . Cl2 Cl 0.75655(8) -0.00861(10) 0.41063(7) 0.0529 1.0000 Uani . . . . . . . O1 O 0.2679(3) 0.8489(4) 0.3550(3) 0.0754 1.0000 Uani . . . . . . . N1 N 0.9596(2) 0.2599(3) 0.60178(17) 0.0316 1.0000 Uani . . . . . . . N2 N 0.8151(2) 0.3227(3) 0.46622(18) 0.0365 1.0000 Uani . . . . . . . N3 N 0.7417(2) 0.3686(3) 0.4021(2) 0.0411 1.0000 Uani . . . . . . . N4 N 0.7356(2) 0.5203(3) 0.41173(19) 0.0382 1.0000 Uani . . . . . . . N5 N 0.4655(3) 0.6904(5) 0.3456(3) 0.0665 1.0000 Uani . . . . . . . C1 C 1.0341(3) 0.2175(4) 0.6686(2) 0.0400 1.0000 Uani . . . . . . . C2 C 1.0859(3) 0.3206(4) 0.7280(2) 0.0436 1.0000 Uani . . . . . . . C3 C 1.0617(3) 0.4733(4) 0.7183(2) 0.0421 1.0000 Uani . . . . . . . C4 C 0.9858(3) 0.5193(4) 0.6493(2) 0.0373 1.0000 Uani . . . . . . . C5 C 0.9364(2) 0.4102(3) 0.59226(19) 0.0289 1.0000 Uani . . . . . . . C6 C 0.8547(2) 0.4431(3) 0.5168(2) 0.0314 1.0000 Uani . . . . . . . C7 C 0.8032(2) 0.5720(4) 0.4815(2) 0.0337 1.0000 Uani . . . . . . . C8 C 0.6545(3) 0.6080(4) 0.3539(2) 0.0418 1.0000 Uani . . . . . . . C9 C 0.5426(4) 0.5655(7) 0.3723(5) 0.0598 0.752(14) Uani . . P . 1 . . C10 C 0.5705(13) 0.668(3) 0.4184(11) 0.0545 0.248(14) Uani . . P . 2 . . C11 C 0.3615(4) 0.6212(6) 0.3204(4) 0.0728 1.0000 Uani . . . . . . . C12 C 0.2812(4) 0.7377(7) 0.2896(3) 0.0732 1.0000 Uani . . . . . . . C13 C 0.4548(4) 0.8051(9) 0.4117(4) 0.0924 1.0000 Uani . . . . . . . C14 C 0.3676(5) 0.9227(7) 0.3791(4) 0.0864 1.0000 Uani . . . . . . . H11 H 1.0502 0.1132 0.6732 0.046(10) 1.0000 Uiso R . . . . . . H21 H 1.1368 0.2866 0.7747 0.054(11) 1.0000 Uiso R . . . . . . H31 H 1.0947 0.5448 0.7572 0.057(12) 1.0000 Uiso R . . . . . . H41 H 0.9676 0.6227 0.6404 0.040(10) 1.0000 Uiso R . . . . . . H71 H 0.8134 0.6726 0.5011 0.039(9) 1.0000 Uiso R . . . . . . H81 H 0.6652 0.7140 0.3652 0.042(9) 0.752(14) Uiso R . P . 1 . . H82 H 0.6620 0.5869 0.2926 0.042(9) 0.752(14) Uiso R . P . 1 . . H83 H 0.6875 0.6914 0.3269 0.042(9) 0.248(14) Uiso R . P . 2 . . H84 H 0.6187 0.5447 0.3082 0.042(9) 0.248(14) Uiso R . P . 2 . . H91 H 0.5439 0.5494 0.4364 0.079(15) 0.752(14) Uiso R . P . 1 . . H92 H 0.5184 0.4719 0.3401 0.079(15) 0.752(14) Uiso R . P . 1 . . H101 H 0.5928 0.7612 0.4468 0.06(4) 0.248(14) Uiso R . P . 2 . . H102 H 0.5580 0.5942 0.4629 0.06(4) 0.248(14) Uiso R . P . 2 . . H111 H 0.3696 0.5492 0.2711 0.088(16) 1.0000 Uiso R . . . . . . H112 H 0.3363 0.5664 0.3710 0.090(17) 1.0000 Uiso R . . . . . . H121 H 0.2115 0.6875 0.2742 0.093(17) 1.0000 Uiso R . . . . . . H122 H 0.3045 0.7878 0.2366 0.048(11) 1.0000 Uiso R . . . . . . H131 H 0.5227 0.8563 0.4273 0.099(13) 1.0000 Uiso . . . . . . . H132 H 0.4350 0.7586 0.4661 0.099(13) 1.0000 Uiso . . . . . . . H141 H 0.3605 1.0003 0.4249 0.102(13) 1.0000 Uiso R . . . . . . H142 H 0.3899 0.9710 0.3250 0.102(13) 1.0000 Uiso 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 Cu1 0.0444(2) 0.02163(19) 0.0440(2) -0.00131(16) -0.01588(17) 0.00087(16) Cl1 0.0567(5) 0.0242(4) 0.0457(5) 0.0024(3) -0.0053(4) 0.0023(3) Cl2 0.0541(5) 0.0333(4) 0.0641(6) -0.0089(4) -0.0246(4) -0.0018(4) O1 0.0537(18) 0.081(2) 0.095(2) 0.006(2) 0.0196(17) 0.0161(16) N1 0.0320(13) 0.0256(12) 0.0358(14) -0.0019(10) -0.0020(11) 0.0014(10) N2 0.0381(14) 0.0265(12) 0.0411(15) -0.0021(11) -0.0123(12) 0.0003(11) N3 0.0461(16) 0.0261(13) 0.0465(16) 0.0002(12) -0.0147(13) 0.0027(11) N4 0.0391(15) 0.0279(13) 0.0441(16) 0.0016(12) -0.0098(12) 0.0031(11) N5 0.054(2) 0.080(3) 0.066(2) 0.020(2) 0.0062(18) 0.0228(19) C1 0.0421(18) 0.0310(16) 0.0436(19) 0.0029(14) -0.0094(15) 0.0063(14) C2 0.0444(19) 0.0458(18) 0.0359(18) -0.0007(15) -0.0149(15) 0.0041(16) C3 0.051(2) 0.0352(17) 0.0369(18) -0.0073(14) -0.0107(15) -0.0040(15) C4 0.0434(18) 0.0266(15) 0.0395(18) -0.0037(13) -0.0054(15) 0.0034(13) C5 0.0270(15) 0.0304(15) 0.0285(15) -0.0007(12) -0.0005(12) 0.0006(12) C6 0.0335(16) 0.0239(13) 0.0353(16) -0.0017(12) -0.0026(13) -0.0004(12) C7 0.0343(16) 0.0267(14) 0.0377(17) -0.0011(12) -0.0060(13) 0.0008(12) C8 0.0418(18) 0.0326(16) 0.0472(19) 0.0055(15) -0.0120(15) 0.0037(14) C9 0.045(3) 0.049(4) 0.084(5) 0.021(3) 0.000(3) 0.005(2) C10 0.049(10) 0.075(14) 0.038(9) 0.019(9) -0.002(7) 0.010(9) C11 0.069(3) 0.066(3) 0.088(4) -0.001(3) 0.028(3) 0.004(2) C12 0.046(2) 0.102(4) 0.069(3) 0.005(3) -0.001(2) -0.002(2) C13 0.060(3) 0.135(6) 0.076(3) 0.021(4) -0.016(3) -0.036(3) C14 0.087(4) 0.071(3) 0.108(4) -0.019(3) 0.044(4) -0.013(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . Cl1 2_756 2.9185(11) yes Cu1 . O1 2_666 2.808(3) yes Cu1 . Cl1 . 2.2647(8) yes Cu1 . Cl2 . 2.2417(9) yes Cu1 . N1 . 2.062(2) yes Cu1 . N2 . 2.024(3) yes Cu1 . C6 . 2.867(3) yes O1 . C12 . 1.402(6) yes O1 . C14 . 1.409(6) yes N1 . C1 . 1.335(4) yes N1 . C5 . 1.351(4) yes N2 . N3 . 1.308(4) yes N2 . C6 . 1.356(4) yes N3 . N4 . 1.338(4) yes N4 . C7 . 1.342(4) yes N4 . C8 . 1.468(4) yes N5 . C9 . 1.479(6) yes N5 . C11 . 1.440(6) yes N5 . C13 . 1.424(8) yes C1 . C2 . 1.374(5) yes C1 . H11 . 0.935 no C2 . C3 . 1.375(5) yes C2 . H21 . 0.936 no C3 . C4 . 1.376(4) yes C3 . H31 . 0.919 no C4 . C5 . 1.377(4) yes C4 . H41 . 0.938 no C5 . C6 . 1.458(4) yes C6 . C7 . 1.373(4) yes C7 . H71 . 0.932 no C8 . C9 . 1.498(7) yes C8 . H81 . 0.950 no C8 . H82 . 0.950 no C9 . H91 . 0.966 no C9 . H92 . 0.980 no C10 . H101 . 0.950 no C10 . H102 . 0.950 no C11 . C12 . 1.465(7) yes C11 . H111 . 0.983 no C11 . H112 . 0.977 no C12 . H121 . 0.976 no C12 . H122 . 0.977 no C13 . C14 . 1.534(9) yes C13 . H131 . 0.962 no C13 . H132 . 0.966 no C14 . H141 . 0.976 no C14 . H142 . 0.980 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 2_756 Cu1 . O1 2_666 163.22(8) yes Cl1 2_756 Cu1 . Cl1 . 85.14(3) yes O1 2_666 Cu1 . Cl1 . 88.33(7) yes Cl1 2_756 Cu1 . Cl2 . 98.44(4) yes O1 2_666 Cu1 . Cl2 . 97.44(8) yes Cl1 . Cu1 . Cl2 . 94.25(3) yes Cl1 2_756 Cu1 . N1 . 86.80(8) yes O1 2_666 Cu1 . N1 . 78.21(11) yes Cl1 . Cu1 . N1 . 93.74(7) yes Cl2 . Cu1 . N1 . 170.79(7) yes Cl1 2_756 Cu1 . N2 . 99.23(9) yes O1 2_666 Cu1 . N2 . 85.47(11) yes Cl1 . Cu1 . N2 . 171.50(8) yes Cl2 . Cu1 . N2 . 92.32(7) yes N1 . Cu1 . N2 . 79.31(10) yes Cl1 2_756 Cu1 . C6 . 97.72(7) yes O1 2_666 Cu1 . C6 . 79.59(10) yes Cl1 . Cu1 . C6 . 147.03(6) yes Cl2 . Cu1 . C6 . 117.55(6) yes N1 . Cu1 . C6 . 53.91(9) yes N2 . Cu1 . C6 . 25.46(9) yes Cu1 2_756 Cl1 . Cu1 . 94.86(3) yes Cu1 2_666 O1 . C12 . 134.6(3) yes Cu1 2_666 O1 . C14 . 111.7(3) yes C12 . O1 . C14 . 109.0(4) yes Cu1 . N1 . C1 . 126.3(2) yes Cu1 . N1 . C5 . 115.63(19) yes C1 . N1 . C5 . 118.1(3) yes Cu1 . N2 . N3 . 134.8(2) yes Cu1 . N2 . C6 . 114.62(19) yes N3 . N2 . C6 . 110.3(2) yes N2 . N3 . N4 . 105.7(2) yes N3 . N4 . C7 . 112.3(2) yes N3 . N4 . C8 . 120.0(3) yes C7 . N4 . C8 . 127.5(3) yes C9 . N5 . C11 . 107.2(4) yes C9 . N5 . C13 . 116.3(5) yes C11 . N5 . C13 . 109.0(4) yes N1 . C1 . C2 . 122.3(3) yes N1 . C1 . H11 . 116.8 no C2 . C1 . H11 . 120.9 no C1 . C2 . C3 . 119.3(3) yes C1 . C2 . H21 . 120.0 no C3 . C2 . H21 . 120.7 no C2 . C3 . C4 . 119.2(3) yes C2 . C3 . H31 . 121.2 no C4 . C3 . H31 . 119.6 no C3 . C4 . C5 . 118.7(3) yes C3 . C4 . H41 . 121.5 no C5 . C4 . H41 . 119.8 no C4 . C5 . N1 . 122.4(3) yes C4 . C5 . C6 . 124.3(3) yes N1 . C5 . C6 . 113.3(2) yes C5 . C6 . N2 . 117.0(3) yes C5 . C6 . Cu1 . 77.16(17) yes N2 . C6 . Cu1 . 39.92(14) yes C5 . C6 . C7 . 135.5(3) yes N2 . C6 . C7 . 107.5(3) yes Cu1 . C6 . C7 . 147.3(2) yes C6 . C7 . N4 . 104.1(3) yes C6 . C7 . H71 . 128.0 no N4 . C7 . H71 . 127.8 no N4 . C8 . C9 . 110.8(3) yes N4 . C8 . H81 . 109.5 no C9 . C8 . H81 . 108.9 no N4 . C8 . H82 . 109.1 no C9 . C8 . H82 . 109.0 no H81 . C8 . H82 . 109.5 no C8 . C9 . N5 . 110.9(4) yes C8 . C9 . H91 . 107.9 no N5 . C9 . H91 . 108.2 no C8 . C9 . H92 . 110.9 no N5 . C9 . H92 . 109.4 no H91 . C9 . H92 . 109.5 no C8 . C10 . N5 . 99.9(10) yes C8 . C10 . H101 . 112.0 no N5 . C10 . H101 . 111.5 no C8 . C10 . H102 . 112.0 no N5 . C10 . H102 . 111.7 no H101 . C10 . H102 . 109.5 no N5 . C11 . C12 . 110.5(4) yes N5 . C11 . H111 . 107.5 no C12 . C11 . H111 . 109.7 no N5 . C11 . H112 . 111.3 no C12 . C11 . H112 . 108.4 no H111 . C11 . H112 . 109.5 no C11 . C12 . O1 . 113.3(4) yes C11 . C12 . H121 . 108.5 no O1 . C12 . H121 . 107.7 no C11 . C12 . H122 . 108.0 no O1 . C12 . H122 . 108.9 no H121 . C12 . H122 . 110.5 no N5 . C13 . C14 . 111.8(4) yes N5 . C13 . H131 . 110.3 no C14 . C13 . H131 . 109.5 no N5 . C13 . H132 . 109.8 no C14 . C13 . H132 . 108.1 no H131 . C13 . H132 . 107.1 no C13 . C14 . O1 . 110.1(4) yes C13 . C14 . H141 . 111.3 no O1 . C14 . H141 . 110.4 no C13 . C14 . H142 . 107.1 no O1 . C14 . H142 . 108.2 no H141 . C14 . H142 . 109.6 no data_MJCAZn _database_code_depnum_ccdc_archive 'CCDC 886727' #TrackingRef 'web_deposit_cif_file_0_TimStorr_1339781702.combined_Storr.cif' #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_sum 'C9 H10 N6 O9 Zn1' _chemical_formula_moiety 'C9 H10 N6 O9 Zn1' _chemical_formula_weight 411.59 #============================================================= # 6. CRYSTAL DATA _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 7.1753(3) _cell_length_b 9.9395(4) _cell_length_c 11.0467(5) _cell_angle_alpha 75.271(3) _cell_angle_beta 74.091(3) _cell_angle_gamma 80.029(3) _cell_volume 728.22(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5504 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 28.15 _cell_measurement_temperature 296(2) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.063 _exptl_crystal_size_mid 0.071 _exptl_crystal_size_max 0.253 _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 1.752 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6038 _exptl_absorpt_correction_T_max 0.7457 #============================================================================= # 7. EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_method '\w/2\q ' _diffrn_ambient_temperature 296(2) _diffrn_reflns_number 9606 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_theta_min 1.964 _diffrn_reflns_theta_max 28.282 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 25.171 _diffrn_measured_fraction_theta_full 0.979 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 #========================================================================== # 8. REFINEMENT DATA # The values actually used during refinement # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _oxford_reflns_threshold_expression_ref I>2.5\s(I) _refine_ls_number_reflns 2624 _refine_ls_number_restraints 0 _refine_ls_number_parameters 235 _oxford_refine_ls_R_factor_ref 0.0305 _refine_ls_wR_factor_ref 0.0315 _refine_ls_goodness_of_fit_ref 1.1068 # The values computed from all data _oxford_reflns_number_all 3484 _refine_ls_R_factor_all 0.0444 _refine_ls_wR_factor_all 0.0456 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2725 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_gt 0.0316 _reflns_number_total 3925 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.152 0.798E-01 0.427E-01 ; _refine_ls_shift/su_max 0.0003784 _refine_diff_density_min -0.44 _refine_diff_density_max 0.44 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -12 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_refine_ls_scale 0.2085(3) _oxford_diffrn_Wilson_B_factor 0 _oxford_diffrn_Wilson_scale 0 # Number of reflections with Friedels Law is 3484 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7230 #--------------------------------------------------------- _chemical_name_systematic ; ; # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary Other # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr # none if no extinction, _refine_ls_extinction_method None #========================================================== # 9. General computing _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_structure_solution ; SIR92 (Altomare et al, 1994) CRYSTALS (Watkin, 1988) ; #=================================================================== # 10. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Zn 0.2839 1.4301 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097 1.3041 'International Tables Vol C 4.2.6.8 and 6.1.1.4' #============================================================================== # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # TODO check _oxford_atom_site_special_shape 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Zn1 Zn 0.78476(4) 0.30086(3) 0.23915(3) 0.0327 1.0000 Uani . . . . . . O1 O 0.9226(2) 0.86448(19) 0.11014(18) 0.0415 1.0000 Uani . . . . . . O2 O 0.7430(2) 1.04472(17) 0.01323(17) 0.0375 1.0000 Uani . . . . . . O3 O 1.0556(3) 0.2029(2) 0.1780(2) 0.0509 1.0000 Uani . . . . . . O4 O 1.1423(3) 0.4105(2) 0.1364(2) 0.0639 1.0000 Uani . . . . . . O5 O 1.3594(3) 0.2320(2) 0.10927(19) 0.0501 1.0000 Uani . . . . . . O6 O 0.6776(3) 0.1067(2) 0.29181(19) 0.0452 1.0000 Uani . . . . . . O7 O 0.4467(3) 0.2538(2) 0.3661(2) 0.0567 1.0000 Uani . . . . . . O8 O 0.3954(3) 0.0384(2) 0.3938(2) 0.0575 1.0000 Uani . . . . . . O9 O 0.7129(3) 0.34705(19) 0.05964(18) 0.0444 1.0000 Uani . . . . . . N1 N 0.8286(3) 0.3027(2) 0.4258(2) 0.0330 1.0000 Uani . . . . . . N2 N 0.6998(3) 0.50733(19) 0.25503(19) 0.0317 1.0000 Uani . . . . . . N3 N 0.6422(3) 0.6189(2) 0.1760(2) 0.0343 1.0000 Uani . . . . . . N4 N 0.6179(3) 0.72429(18) 0.23551(18) 0.0279 1.0000 Uani . . . . . . N5 N 1.1897(3) 0.2840(2) 0.1401(2) 0.0404 1.0000 Uani . . . . . . N6 N 0.5016(3) 0.1315(2) 0.3528(2) 0.0386 1.0000 Uani . . . . . . C1 C 0.8911(4) 0.1916(3) 0.5078(3) 0.0458 1.0000 Uani . . . . . . C2 C 0.9063(4) 0.1974(3) 0.6282(3) 0.0471 1.0000 Uani . . . . . . C3 C 0.8547(4) 0.3241(3) 0.6651(3) 0.0401 1.0000 Uani . . . . . . C4 C 0.7895(3) 0.4406(3) 0.5817(2) 0.0335 1.0000 Uani . . . . . . C5 C 0.7787(3) 0.4261(2) 0.4624(2) 0.0277 1.0000 Uani . . . . . . C6 C 0.7124(3) 0.5397(2) 0.3646(2) 0.0270 1.0000 Uani . . . . . . C7 C 0.6597(3) 0.6814(2) 0.3518(2) 0.0285 1.0000 Uani . . . . . . C8 C 0.5779(3) 0.8664(2) 0.1643(2) 0.0313 1.0000 Uani . . . . . . C9 C 0.7669(3) 0.9255(2) 0.0923(2) 0.0293 1.0000 Uani . . . . . . H11 H 0.9271 0.1056 0.4797 0.072(11) 1.0000 Uiso R . . . . . H21 H 0.9507 0.1174 0.6833 0.044(8) 1.0000 Uiso R . . . . . H22 H 0.8671 1.0762 -0.0289 0.077(12) 1.0000 Uiso R . . . . . H31 H 0.8632 0.3313 0.7470 0.046(8) 1.0000 Uiso R . . . . . H41 H 0.7536 0.5299 0.6038 0.038(7) 1.0000 Uiso R . . . . . H71 H 0.6523 0.7385 0.4107 0.040(7) 1.0000 Uiso R . . . . . H81 H 0.5066 0.9243 0.2245 0.042(7) 1.0000 Uiso R . . . . . H82 H 0.5029 0.8657 0.1042 0.034(7) 1.0000 Uiso R . . . . . H91 H 0.6627 0.4396 0.0250 0.28(3) 1.0000 Uiso R . . . . . H92 H 0.7305 0.2755 0.0132 0.28(3) 1.0000 Uiso 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 0.03427(15) 0.02627(13) 0.03931(16) -0.01056(10) -0.00861(11) -0.00321(10) O1 0.0289(8) 0.0401(10) 0.0448(10) 0.0075(8) -0.0095(7) 0.0004(7) O2 0.0319(9) 0.0297(8) 0.0454(10) 0.0042(7) -0.0136(7) -0.0004(7) O3 0.0346(10) 0.0575(12) 0.0648(13) -0.0269(10) -0.0068(9) -0.0042(8) O4 0.0630(14) 0.0488(13) 0.0655(15) -0.0100(11) 0.0031(11) -0.0022(10) O5 0.0312(9) 0.0710(14) 0.0456(11) -0.0150(10) -0.0065(8) 0.0001(9) O6 0.0439(11) 0.0460(11) 0.0472(11) -0.0173(9) -0.0021(9) -0.0131(8) O7 0.0703(14) 0.0418(11) 0.0664(14) -0.0244(10) -0.0234(11) 0.0012(10) O8 0.0599(13) 0.0592(13) 0.0527(12) -0.0084(10) -0.0006(10) -0.0316(11) O9 0.0558(12) 0.0381(10) 0.0430(10) -0.0096(8) -0.0161(9) -0.0068(8) N1 0.0335(10) 0.0271(9) 0.0400(11) -0.0071(8) -0.0135(9) -0.0002(7) N2 0.0372(10) 0.0252(9) 0.0347(10) -0.0076(8) -0.0121(8) -0.0013(7) N3 0.0416(11) 0.0261(9) 0.0374(11) -0.0085(8) -0.0134(9) -0.0011(8) N4 0.0286(9) 0.0236(9) 0.0322(10) -0.0065(7) -0.0080(8) -0.0029(7) N5 0.0363(11) 0.0526(14) 0.0324(11) -0.0119(10) -0.0080(9) -0.0018(10) N6 0.0457(12) 0.0408(12) 0.0325(11) -0.0098(9) -0.0074(9) -0.0143(9) C1 0.0514(16) 0.0306(12) 0.0568(17) -0.0050(12) -0.0237(13) 0.0019(11) C2 0.0475(15) 0.0403(14) 0.0531(17) 0.0047(12) -0.0273(13) -0.0017(11) C3 0.0368(13) 0.0481(15) 0.0369(13) -0.0028(11) -0.0151(11) -0.0081(11) C4 0.0305(11) 0.0368(12) 0.0352(12) -0.0095(10) -0.0088(9) -0.0052(9) C5 0.0230(10) 0.0268(10) 0.0334(11) -0.0049(9) -0.0077(8) -0.0038(8) C6 0.0229(10) 0.0290(10) 0.0303(11) -0.0080(9) -0.0062(8) -0.0041(8) C7 0.0283(11) 0.0284(11) 0.0315(11) -0.0097(9) -0.0083(9) -0.0037(8) C8 0.0316(11) 0.0248(10) 0.0377(12) -0.0053(9) -0.0122(9) 0.0002(8) C9 0.0319(11) 0.0276(11) 0.0288(11) -0.0057(9) -0.0101(9) -0.0002(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Zn1 . O3 . 2.0348(19) yes Zn1 . O4 . 2.793(2) yes Zn1 . O6 . 2.0864(18) yes Zn1 . O7 . 2.503(2) yes Zn1 . O9 . 2.1036(19) yes Zn1 . N1 . 2.174(2) yes Zn1 . N2 . 2.0749(19) yes Zn1 . N6 . 2.693(2) yes O1 . C9 . 1.217(3) yes O2 . C9 . 1.297(3) yes O2 . H22 . 0.950 no O3 . N5 . 1.275(3) yes O4 . N5 . 1.238(3) yes O5 . N5 . 1.229(3) yes O6 . N6 . 1.273(3) yes O7 . N6 . 1.244(3) yes O8 . N6 . 1.218(3) yes O9 . H91 . 0.950 no O9 . H92 . 0.950 no N1 . C1 . 1.335(3) yes N1 . C5 . 1.349(3) yes N2 . N3 . 1.308(3) yes N2 . C6 . 1.358(3) yes N3 . N4 . 1.335(3) yes N4 . C7 . 1.345(3) yes N4 . C8 . 1.454(3) yes C1 . C2 . 1.380(4) yes C1 . H11 . 0.953 no C2 . C3 . 1.380(4) yes C2 . H21 . 0.937 no C3 . C4 . 1.384(3) yes C3 . H31 . 0.945 no C4 . C5 . 1.385(3) yes C4 . H41 . 0.954 no C5 . C6 . 1.464(3) yes C6 . C7 . 1.375(3) yes C7 . H71 . 0.953 no C8 . C9 . 1.505(3) yes C8 . H81 . 0.970 no C8 . H82 . 0.964 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 . Zn1 . O4 . 50.17(7) yes O3 . Zn1 . O6 . 88.49(8) yes O4 . Zn1 . O6 . 138.62(7) yes O3 . Zn1 . O7 . 142.21(8) yes O4 . Zn1 . O7 . 164.19(7) yes O6 . Zn1 . O7 . 54.70(7) yes O3 . Zn1 . O9 . 95.61(8) yes O4 . Zn1 . O9 . 93.72(7) yes O6 . Zn1 . O9 . 92.02(7) yes O7 . Zn1 . O9 . 94.10(8) yes O3 . Zn1 . N1 . 94.12(8) yes O4 . Zn1 . N1 . 85.54(8) yes O6 . Zn1 . N1 . 97.32(7) yes O7 . Zn1 . N1 . 83.68(7) yes O9 . Zn1 . N1 . 166.67(7) yes O3 . Zn1 . N2 . 129.71(8) yes O4 . Zn1 . N2 . 79.67(7) yes O6 . Zn1 . N2 . 141.26(8) yes O7 . Zn1 . N2 . 86.56(7) yes O9 . Zn1 . N2 . 90.40(7) yes O3 . Zn1 . N6 . 115.50(8) yes O4 . Zn1 . N6 . 164.74(7) yes O6 . Zn1 . N6 . 27.32(7) yes O7 . Zn1 . N6 . 27.39(7) yes O9 . Zn1 . N6 . 93.08(7) yes N1 . Zn1 . N2 . 76.36(7) yes N1 . Zn1 . N6 . 90.93(7) yes N2 . Zn1 . N6 . 113.94(7) yes C9 . O2 . H22 . 108.7 no Zn1 . O3 . N5 . 113.66(16) yes Zn1 . O4 . N5 . 77.60(15) yes Zn1 . O6 . N6 . 103.91(15) yes Zn1 . O7 . N6 . 84.83(15) yes Zn1 . O9 . H91 . 119.9 no Zn1 . O9 . H92 . 120.0 no H91 . O9 . H92 . 120.1 no Zn1 . N1 . C1 . 125.53(18) yes Zn1 . N1 . C5 . 116.02(15) yes C1 . N1 . C5 . 118.4(2) yes Zn1 . N2 . N3 . 132.45(15) yes Zn1 . N2 . C6 . 116.62(15) yes N3 . N2 . C6 . 110.85(19) yes N2 . N3 . N4 . 105.66(18) yes N3 . N4 . C7 . 112.11(18) yes N3 . N4 . C8 . 118.60(19) yes C7 . N4 . C8 . 128.72(19) yes O3 . N5 . O4 . 118.4(2) yes O3 . N5 . O5 . 118.1(2) yes O4 . N5 . O5 . 123.5(2) yes O6 . N6 . O7 . 116.5(2) yes O6 . N6 . O8 . 120.3(2) yes O7 . N6 . O8 . 123.2(2) yes O6 . N6 . Zn1 . 48.77(11) yes O7 . N6 . Zn1 . 67.78(14) yes O8 . N6 . Zn1 . 168.89(19) yes N1 . C1 . C2 . 123.0(3) yes N1 . C1 . H11 . 117.1 no C2 . C1 . H11 . 119.9 no C1 . C2 . C3 . 118.3(2) yes C1 . C2 . H21 . 120.7 no C3 . C2 . H21 . 121.0 no C2 . C3 . C4 . 119.7(2) yes C2 . C3 . H31 . 120.2 no C4 . C3 . H31 . 120.1 no C3 . C4 . C5 . 118.5(2) yes C3 . C4 . H41 . 121.9 no C5 . C4 . H41 . 119.7 no C4 . C5 . N1 . 122.2(2) yes C4 . C5 . C6 . 124.6(2) yes N1 . C5 . C6 . 113.3(2) yes C5 . C6 . N2 . 117.66(19) yes C5 . C6 . C7 . 135.5(2) yes N2 . C6 . C7 . 106.84(19) yes C6 . C7 . N4 . 104.54(19) yes C6 . C7 . H71 . 129.0 no N4 . C7 . H71 . 126.4 no N4 . C8 . C9 . 109.65(18) yes N4 . C8 . H81 . 109.2 no C9 . C8 . H81 . 108.3 no N4 . C8 . H82 . 109.5 no C9 . C8 . H82 . 109.7 no H81 . C8 . H82 . 110.4 no C8 . C9 . O2 . 112.96(19) yes C8 . C9 . O1 . 121.4(2) yes O2 . C9 . O1 . 125.6(2) yes