# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Housecroft, Catherine' 'Constable, Edwin' 'Meuwly, Markus' 'Rudd, Jennifer' 'Chaurin, Valerie' 'Bozic-Weber, Biljana' 'Neuburger, Markus' 'Schoenhofer, Ewald' 'Siegfried, Liselott' _publ_contact_author_name 'Housecroft, Catherine' _publ_contact_author_email Catherine.Housecroft@unibas.ch data_Cu(Me2bpy)2 _database_code_depnum_ccdc_archive 'CCDC 885553' #TrackingRef '- Cu(Me2bpy)2.cif' _audit_creation_date 11-10-10 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'jar95_123k_0ma in P2(1)/c' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.7104(6) _cell_length_b 21.9632(11) _cell_length_c 8.7001(5) _cell_angle_alpha 90 _cell_angle_beta 94.692(2) _cell_angle_gamma 90 _cell_volume 2420.6(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 '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' _cell_formula_units_Z 4 # Given Formula = C24 H24 Cu1 F6 N4 P1 # Dc = 1.58 Fooo = 1176.00 Mu = 10.36 M = 576.99 # Found Formula = C24 H24 Cu1 F6 N4 P1 # Dc = 1.58 FOOO = 1176.00 Mu = 10.36 M = 576.99 _chemical_formula_sum 'C24 H24 Cu1 F6 N4 P1' _chemical_formula_moiety 'C24 H24 Cu1 N4, F6 P' _chemical_compound_source ? _chemical_formula_weight 576.99 _cell_measurement_reflns_used 9888 _cell_measurement_theta_min 3 _cell_measurement_theta_max 36 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_max 0.210 _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1176 _exptl_absorpt_coefficient_mu 1.036 # Sheldrick geometric approximatio 0.87 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.94 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 35645 _reflns_number_total 8817 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 8817 # Theoretical number of reflections is about 17649 _diffrn_reflns_theta_min 1.856 _diffrn_reflns_theta_max 32.588 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.588 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -19 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 33 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.35 _refine_diff_density_max 0.54 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 6818 _refine_ls_number_restraints 0 _refine_ls_number_parameters 325 _oxford_refine_ls_R_factor_ref 0.0274 _refine_ls_wR_factor_ref 0.0293 _refine_ls_goodness_of_fit_ref 1.0891 _refine_ls_shift/su_max 0.0016108 _refine_ls_shift/su_mean 0.0000845 # The values computed from all data _oxford_reflns_number_all 8801 _refine_ls_R_factor_all 0.0370 _refine_ls_wR_factor_all 0.0450 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7537 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_gt 0.0312 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _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: 0.186 0.186 0.100 0.310E-01 0.455E-02 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 Cu1 Cu 0.797948(10) 0.623983(6) 0.414035(15) 0.0159 1.0000 Uani . . . . . . N1 N 0.67509(7) 0.67277(4) 0.48301(10) 0.0153 1.0000 Uani . . . . . . N2 N 0.72406(7) 0.55652(4) 0.52680(10) 0.0149 1.0000 Uani . . . . . . N3 N 0.82863(7) 0.60298(4) 0.19315(10) 0.0151 1.0000 Uani . . . . . . N4 N 0.95102(7) 0.65169(4) 0.42438(10) 0.0140 1.0000 Uani . . . . . . C1 C 0.65649(9) 0.73250(5) 0.45918(13) 0.0191 1.0000 Uani . . . . . . C2 C 0.56662(10) 0.76054(6) 0.50752(15) 0.0262 1.0000 Uani . . . . . . C3 C 0.49521(10) 0.72664(6) 0.58280(16) 0.0290 1.0000 Uani . . . . . . C4 C 0.51463(9) 0.66519(6) 0.60907(15) 0.0244 1.0000 Uani . . . . . . C5 C 0.60552(8) 0.63963(5) 0.55808(12) 0.0157 1.0000 Uani . . . . . . C6 C 0.63282(8) 0.57457(5) 0.58262(12) 0.0149 1.0000 Uani . . . . . . C7 C 0.56960(8) 0.53437(5) 0.65813(13) 0.0187 1.0000 Uani . . . . . . C8 C 0.60070(9) 0.47396(5) 0.67356(14) 0.0220 1.0000 Uani . . . . . . C9 C 0.69278(9) 0.45532(5) 0.61311(14) 0.0214 1.0000 Uani . . . . . . C10 C 0.75349(8) 0.49773(5) 0.54050(13) 0.0174 1.0000 Uani . . . . . . C11 C 0.73682(10) 0.76728(6) 0.37838(15) 0.0249 1.0000 Uani . . . . . . C12 C 0.85482(9) 0.48051(6) 0.47528(16) 0.0246 1.0000 Uani . . . . . . C13 C 0.76352(8) 0.57470(5) 0.08605(13) 0.0180 1.0000 Uani . . . . . . C14 C 0.79976(10) 0.55375(5) -0.05161(13) 0.0216 1.0000 Uani . . . . . . C15 C 0.90481(10) 0.56090(6) -0.07697(14) 0.0256 1.0000 Uani . . . . . . C16 C 0.97245(9) 0.58969(6) 0.03347(14) 0.0226 1.0000 Uani . . . . . . C17 C 0.93138(8) 0.61088(5) 0.16695(12) 0.0150 1.0000 Uani . . . . . . C18 C 0.99680(8) 0.64273(5) 0.29051(12) 0.0143 1.0000 Uani . . . . . . C19 C 1.09834(8) 0.66295(5) 0.27024(13) 0.0176 1.0000 Uani . . . . . . C20 C 1.15521(8) 0.69258(5) 0.39105(14) 0.0192 1.0000 Uani . . . . . . C21 C 1.10937(8) 0.70103(5) 0.52846(14) 0.0189 1.0000 Uani . . . . . . C22 C 1.00629(8) 0.68063(5) 0.54111(12) 0.0160 1.0000 Uani . . . . . . C23 C 0.65157(9) 0.56521(6) 0.12203(16) 0.0261 1.0000 Uani . . . . . . C24 C 0.95203(9) 0.69151(6) 0.68489(13) 0.0227 1.0000 Uani . . . . . . P1 P 0.29951(2) 0.632972(13) -0.07919(3) 0.0184 1.0000 Uani . . . . . . F1 F 0.30415(9) 0.66872(5) 0.08121(12) 0.0502 1.0000 Uani . . . . . . F2 F 0.26007(8) 0.57415(4) 0.00577(13) 0.0425 1.0000 Uani . . . . . . F3 F 0.29674(9) 0.59734(6) -0.23808(12) 0.0511 1.0000 Uani . . . . . . F4 F 0.33844(7) 0.69273(4) -0.16159(12) 0.0368 1.0000 Uani . . . . . . F5 F 0.17971(6) 0.65360(5) -0.11454(12) 0.0426 1.0000 Uani . . . . . . F6 F 0.41977(7) 0.61292(5) -0.04272(13) 0.0454 1.0000 Uani . . . . . . H21 H 0.5553 0.8025 0.4876 0.0328 1.0000 Uiso R . . . . . H31 H 0.4333 0.7449 0.6162 0.0350 1.0000 Uiso R . . . . . H41 H 0.4667 0.6415 0.6596 0.0296 1.0000 Uiso R . . . . . H71 H 0.5062 0.5485 0.6967 0.0232 1.0000 Uiso R . . . . . H81 H 0.5596 0.4460 0.7268 0.0279 1.0000 Uiso R . . . . . H91 H 0.7159 0.4142 0.6221 0.0270 1.0000 Uiso R . . . . . H113 H 0.7133 0.8069 0.3518 0.0405 1.0000 Uiso R . . . . . H112 H 0.8018 0.7692 0.4412 0.0406 1.0000 Uiso R . . . . . H111 H 0.7514 0.7463 0.2851 0.0403 1.0000 Uiso R . . . . . H123 H 0.8767 0.4408 0.5058 0.0403 1.0000 Uiso R . . . . . H122 H 0.9091 0.5090 0.5055 0.0407 1.0000 Uiso R . . . . . H121 H 0.8456 0.4817 0.3643 0.0400 1.0000 Uiso R . . . . . H141 H 0.7523 0.5342 -0.1275 0.0266 1.0000 Uiso R . . . . . H151 H 0.9301 0.5466 -0.1704 0.0316 1.0000 Uiso R . . . . . H161 H 1.0456 0.5945 0.0188 0.0276 1.0000 Uiso R . . . . . H191 H 1.1275 0.6569 0.1755 0.0207 1.0000 Uiso R . . . . . H201 H 1.2238 0.7074 0.3789 0.0235 1.0000 Uiso R . . . . . H211 H 1.1459 0.7212 0.6128 0.0238 1.0000 Uiso R . . . . . H233 H 0.6071 0.5599 0.0304 0.0408 1.0000 Uiso R . . . . . H232 H 0.6273 0.5997 0.1771 0.0403 1.0000 Uiso R . . . . . H231 H 0.6474 0.5300 0.1873 0.0411 1.0000 Uiso R . . . . . H243 H 0.9994 0.6896 0.7733 0.0369 1.0000 Uiso R . . . . . H242 H 0.9193 0.7313 0.6782 0.0366 1.0000 Uiso R . . . . . H241 H 0.8968 0.6620 0.6908 0.0358 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 0.01191(5) 0.01870(6) 0.01788(6) -0.00057(5) 0.00635(4) -0.00072(4) N1 0.0138(4) 0.0173(4) 0.0154(4) 0.0014(3) 0.0041(3) 0.0007(3) N2 0.0118(3) 0.0173(4) 0.0159(4) 0.0005(3) 0.0028(3) 0.0003(3) N3 0.0135(4) 0.0163(4) 0.0157(4) 0.0006(3) 0.0023(3) -0.0004(3) N4 0.0124(3) 0.0148(4) 0.0152(4) 0.0002(3) 0.0033(3) 0.0005(3) C1 0.0194(5) 0.0196(5) 0.0189(5) 0.0030(4) 0.0049(4) 0.0029(4) C2 0.0271(6) 0.0215(5) 0.0313(6) 0.0060(4) 0.0111(5) 0.0097(4) C3 0.0249(6) 0.0291(6) 0.0354(7) 0.0081(5) 0.0161(5) 0.0131(5) C4 0.0189(5) 0.0272(6) 0.0290(6) 0.0069(4) 0.0132(4) 0.0067(4) C5 0.0135(4) 0.0185(4) 0.0158(4) 0.0022(3) 0.0045(3) 0.0021(3) C6 0.0115(4) 0.0186(4) 0.0149(4) 0.0012(3) 0.0021(3) -0.0002(3) C7 0.0141(4) 0.0222(5) 0.0202(5) 0.0034(4) 0.0037(3) -0.0028(4) C8 0.0187(5) 0.0218(5) 0.0256(5) 0.0042(4) 0.0025(4) -0.0057(4) C9 0.0199(5) 0.0173(5) 0.0269(5) 0.0022(4) 0.0011(4) -0.0018(4) C10 0.0145(4) 0.0171(4) 0.0204(5) -0.0003(4) 0.0009(3) 0.0006(3) C11 0.0249(5) 0.0200(5) 0.0309(6) 0.0078(4) 0.0087(4) 0.0000(4) C12 0.0190(5) 0.0205(5) 0.0353(6) -0.0004(4) 0.0080(4) 0.0045(4) C13 0.0166(4) 0.0184(5) 0.0187(5) 0.0018(4) 0.0001(3) -0.0013(3) C14 0.0260(5) 0.0218(5) 0.0169(5) -0.0018(4) 0.0008(4) -0.0038(4) C15 0.0303(6) 0.0289(6) 0.0188(5) -0.0058(4) 0.0086(4) -0.0048(5) C16 0.0215(5) 0.0271(5) 0.0204(5) -0.0046(4) 0.0096(4) -0.0038(4) C17 0.0142(4) 0.0159(4) 0.0152(4) 0.0005(3) 0.0039(3) -0.0010(3) C18 0.0126(4) 0.0140(4) 0.0168(4) 0.0006(3) 0.0040(3) 0.0001(3) C19 0.0138(4) 0.0189(5) 0.0211(5) 0.0011(4) 0.0066(3) -0.0012(3) C20 0.0132(4) 0.0179(5) 0.0269(5) 0.0005(4) 0.0043(4) -0.0025(3) C21 0.0155(4) 0.0178(5) 0.0234(5) -0.0019(4) 0.0012(4) -0.0017(3) C22 0.0151(4) 0.0159(4) 0.0173(4) -0.0008(3) 0.0027(3) 0.0004(3) C23 0.0160(5) 0.0333(6) 0.0287(6) -0.0034(5) 0.0001(4) -0.0042(4) C24 0.0212(5) 0.0297(6) 0.0178(5) -0.0057(4) 0.0049(4) -0.0030(4) P1 0.01460(11) 0.01899(12) 0.02216(13) 0.00175(10) 0.00534(9) -0.00150(9) F1 0.0497(6) 0.0676(7) 0.0367(5) -0.0236(5) 0.0235(4) -0.0306(5) F2 0.0389(5) 0.0309(4) 0.0586(6) 0.0193(4) 0.0100(4) -0.0083(4) F3 0.0515(6) 0.0639(7) 0.0402(5) -0.0278(5) 0.0180(4) -0.0227(5) F4 0.0338(4) 0.0267(4) 0.0535(5) 0.0140(4) 0.0257(4) 0.0018(3) F5 0.0163(3) 0.0609(6) 0.0514(6) 0.0231(5) 0.0084(3) 0.0070(4) F6 0.0181(4) 0.0546(6) 0.0634(7) 0.0204(5) 0.0030(4) 0.0064(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.11903(9) 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 . N1 . 2.0248(9) yes Cu1 . N2 . 2.0472(9) yes Cu1 . N3 . 2.0447(9) yes Cu1 . N4 . 2.0335(9) yes N1 . C1 . 1.3461(14) yes N1 . C5 . 1.3538(13) yes N2 . C6 . 1.3527(13) yes N2 . C10 . 1.3469(14) yes N3 . C13 . 1.3464(14) yes N3 . C17 . 1.3551(13) yes N4 . C18 . 1.3581(13) yes N4 . C22 . 1.3462(14) yes C1 . C2 . 1.3927(15) yes C1 . C11 . 1.4958(16) yes C2 . C3 . 1.3800(18) yes C2 . H21 . 0.946 no C3 . C4 . 1.3876(18) yes C3 . H31 . 0.950 no C4 . C5 . 1.3894(14) yes C4 . H41 . 0.937 no C5 . C6 . 1.4819(15) yes C6 . C7 . 1.3939(14) yes C7 . C8 . 1.3878(16) yes C7 . H71 . 0.950 no C8 . C9 . 1.3838(16) yes C8 . H81 . 0.952 no C9 . C10 . 1.3935(15) yes C9 . H91 . 0.950 no C10 . C12 . 1.4978(15) yes C11 . H113 . 0.943 no C11 . H112 . 0.953 no C11 . H111 . 0.964 no C12 . H123 . 0.947 no C12 . H122 . 0.953 no C12 . H121 . 0.963 no C13 . C14 . 1.3958(16) yes C13 . C23 . 1.4964(16) yes C14 . C15 . 1.3801(17) yes C14 . H141 . 0.959 no C15 . C16 . 1.3881(17) yes C15 . H151 . 0.951 no C16 . C17 . 1.3916(15) yes C16 . H161 . 0.954 no C17 . C18 . 1.4800(15) yes C18 . C19 . 1.3897(14) yes C19 . C20 . 1.3879(16) yes C19 . H191 . 0.941 no C20 . C21 . 1.3846(16) yes C20 . H201 . 0.945 no C21 . C22 . 1.3975(15) yes C21 . H211 . 0.946 no C22 . C24 . 1.4962(15) yes C23 . H233 . 0.946 no C23 . H232 . 0.961 no C23 . H231 . 0.963 no C24 . H243 . 0.938 no C24 . H242 . 0.969 no C24 . H241 . 0.959 no P1 . F1 . 1.5981(10) yes P1 . F2 . 1.5897(9) yes P1 . F3 . 1.5864(10) yes P1 . F4 . 1.5935(8) yes P1 . F5 . 1.5943(9) yes P1 . F6 . 1.5974(9) yes 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 N1 . Cu1 . N2 . 81.13(4) yes N1 . Cu1 . N3 . 127.51(4) yes N2 . Cu1 . N3 . 114.67(4) yes N1 . Cu1 . N4 . 125.93(4) yes N2 . Cu1 . N4 . 132.08(4) yes N3 . Cu1 . N4 . 81.59(3) yes Cu1 . N1 . C1 . 126.88(7) yes Cu1 . N1 . C5 . 114.11(7) yes C1 . N1 . C5 . 119.00(9) yes Cu1 . N2 . C6 . 113.60(7) yes Cu1 . N2 . C10 . 126.97(7) yes C6 . N2 . C10 . 119.29(9) yes Cu1 . N3 . C13 . 126.93(7) yes Cu1 . N3 . C17 . 112.94(7) yes C13 . N3 . C17 . 119.27(9) yes Cu1 . N4 . C18 . 113.22(7) yes Cu1 . N4 . C22 . 127.81(7) yes C18 . N4 . C22 . 118.78(9) yes N1 . C1 . C2 . 121.51(10) yes N1 . C1 . C11 . 116.87(9) yes C2 . C1 . C11 . 121.62(10) yes C1 . C2 . C3 . 119.49(11) yes C1 . C2 . H21 . 119.4 no C3 . C2 . H21 . 121.1 no C2 . C3 . C4 . 119.21(11) yes C2 . C3 . H31 . 120.7 no C4 . C3 . H31 . 120.1 no C3 . C4 . C5 . 118.79(11) yes C3 . C4 . H41 . 120.2 no C5 . C4 . H41 . 121.0 no C4 . C5 . N1 . 122.00(10) yes C4 . C5 . C6 . 122.31(9) yes N1 . C5 . C6 . 115.69(9) yes C5 . C6 . N2 . 115.37(9) yes C5 . C6 . C7 . 122.78(9) yes N2 . C6 . C7 . 121.86(10) yes C6 . C7 . C8 . 118.71(10) yes C6 . C7 . H71 . 119.9 no C8 . C7 . H71 . 121.4 no C7 . C8 . C9 . 119.29(10) yes C7 . C8 . H81 . 120.1 no C9 . C8 . H81 . 120.6 no C8 . C9 . C10 . 119.43(10) yes C8 . C9 . H91 . 121.0 no C10 . C9 . H91 . 119.6 no C9 . C10 . N2 . 121.39(10) yes C9 . C10 . C12 . 121.89(10) yes N2 . C10 . C12 . 116.72(10) yes C1 . C11 . H113 . 111.8 no C1 . C11 . H112 . 110.2 no H113 . C11 . H112 . 110.0 no C1 . C11 . H111 . 109.7 no H113 . C11 . H111 . 108.3 no H112 . C11 . H111 . 106.7 no C10 . C12 . H123 . 111.6 no C10 . C12 . H122 . 110.8 no H123 . C12 . H122 . 109.9 no C10 . C12 . H121 . 109.6 no H123 . C12 . H121 . 108.3 no H122 . C12 . H121 . 106.6 no N3 . C13 . C14 . 121.24(10) yes N3 . C13 . C23 . 117.43(10) yes C14 . C13 . C23 . 121.32(10) yes C13 . C14 . C15 . 119.41(11) yes C13 . C14 . H141 . 120.3 no C15 . C14 . H141 . 120.2 no C14 . C15 . C16 . 119.58(11) yes C14 . C15 . H151 . 119.9 no C16 . C15 . H151 . 120.6 no C15 . C16 . C17 . 118.46(11) yes C15 . C16 . H161 . 120.8 no C17 . C16 . H161 . 120.7 no C16 . C17 . N3 . 122.01(10) yes C16 . C17 . C18 . 122.51(9) yes N3 . C17 . C18 . 115.48(9) yes C17 . C18 . N4 . 115.89(8) yes C17 . C18 . C19 . 122.09(9) yes N4 . C18 . C19 . 122.01(10) yes C18 . C19 . C20 . 119.03(10) yes C18 . C19 . H191 . 120.2 no C20 . C19 . H191 . 120.8 no C19 . C20 . C21 . 119.13(10) yes C19 . C20 . H201 . 120.4 no C21 . C20 . H201 . 120.5 no C20 . C21 . C22 . 119.24(10) yes C20 . C21 . H211 . 121.2 no C22 . C21 . H211 . 119.5 no C21 . C22 . N4 . 121.78(10) yes C21 . C22 . C24 . 120.92(10) yes N4 . C22 . C24 . 117.28(9) yes C13 . C23 . H233 . 110.7 no C13 . C23 . H232 . 110.1 no H233 . C23 . H232 . 108.9 no C13 . C23 . H231 . 109.5 no H233 . C23 . H231 . 109.9 no H232 . C23 . H231 . 107.7 no C22 . C24 . H243 . 111.7 no C22 . C24 . H242 . 108.6 no H243 . C24 . H242 . 109.5 no C22 . C24 . H241 . 109.1 no H243 . C24 . H241 . 110.4 no H242 . C24 . H241 . 107.4 no F1 . P1 . F2 . 89.07(6) yes F1 . P1 . F3 . 179.15(6) yes F2 . P1 . F3 . 91.08(6) yes F1 . P1 . F4 . 89.86(6) yes F2 . P1 . F4 . 178.88(6) yes F3 . P1 . F4 . 89.99(6) yes F1 . P1 . F5 . 89.73(6) yes F2 . P1 . F5 . 89.32(5) yes F3 . P1 . F5 . 91.11(6) yes F4 . P1 . F5 . 90.34(5) yes F1 . P1 . F6 . 89.75(6) yes F2 . P1 . F6 . 90.95(5) yes F3 . P1 . F6 . 89.41(6) yes F4 . P1 . F6 . 89.37(5) yes F5 . P1 . F6 . 179.41(6) yes _iucr_refine_instruction_details_constraints ; # # Punched on 10/10/11 at 17:04:46 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 11,X'S) H ( 113,X'S) H ( 112,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 123,X'S) H ( 122,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 23,X'S) H ( 233,X'S) H ( 232,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 243,X'S) H ( 242,X'S) H ( 241,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 10/10/11 at 17:04:46 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Attachment '- Cu_complex-squeeze.cif' data_Cu_complex-squeeze _database_code_depnum_ccdc_archive 'CCDC 885554' #TrackingRef '- Cu_complex-squeeze.cif' _audit_creation_date 12-01-04 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'bb164a_123k_0ma in P4/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 15.1209(2) _cell_length_b 15.1209(2) _cell_length_c 18.2971(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4183.48(12) _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P 4/n' _symmetry_space_group_name_Hall '-P 4a' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -y+1/2,x,z y+1/2,-x,-z -x+1/2,-y+1/2,z x+1/2,y+1/2,-z y,-x+1/2,z -y,x+1/2,-z 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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 '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' _cell_formula_units_Z 2 # Given Formula = C101 H84 Cu1 F6 N8 O3 P1 # Dc = 1.32 Fooo = 1660.00 Mu = 3.52 M = 416.58 # Found Formula = C100 H76 Cu1 F6 N8 P1 # Dc = 1.27 FOOO = 1660.00 Mu = 3.47 M = 399.57 _chemical_formula_sum 'C100 H76 Cu1 F6 N8 P1' _chemical_formula_moiety 'C100 H76 Cu1 N8, F6 P' _chemical_compound_source ? _chemical_formula_weight 1598.28 _cell_measurement_reflns_used 8009 _cell_measurement_theta_min 4 _cell_measurement_theta_max 32 _cell_measurement_temperature 123 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_max 0.210 _exptl_crystal_density_diffrn 1.27 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1660 _exptl_absorpt_coefficient_mu 0.347 # Sheldrick geometric approximatio 0.94 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 49103 _reflns_number_total 7090 _diffrn_reflns_av_R_equivalents 0.062 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 7090 # Theoretical number of reflections is about 14133 _diffrn_reflns_theta_min 1.747 _diffrn_reflns_theta_max 31.714 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.714 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _reflns_limit_h_min -15 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.35 _refine_diff_density_max 0.48 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 3503 _refine_ls_number_restraints 27 _refine_ls_number_parameters 276 _oxford_refine_ls_R_factor_ref 0.0413 _refine_ls_wR_factor_ref 0.0465 _refine_ls_goodness_of_fit_ref 1.0236 _refine_ls_shift/su_max 0.0003856 _refine_ls_shift/su_mean 0.0000426 # The values computed from all data _oxford_reflns_number_all 7074 _refine_ls_R_factor_all 0.0902 _refine_ls_wR_factor_all 0.1193 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4382 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_gt 0.0524 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _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: 0.231 0.211 0.800E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. ; _vrf_PLAT051_I ; PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 16.88 Perc. RESPONSE: Checkcif seems not to recognize that P1 is on a special position. ; # end Validation Reply Form # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 Cu1 Cu 0.7500 0.2500 0.0000 0.0245 1.0000 Uani S T . . . . N1 N 0.83167(11) 0.28016(11) 0.08502(8) 0.0245 1.0000 Uani . . . . . . N2 N 1.04143(12) 0.51115(14) -0.30362(10) 0.0362 1.0000 Uani . . . . . . C1 C 0.91775(14) 0.30283(14) 0.07886(10) 0.0290 1.0000 Uani . . . . . . C2 C 0.97332(15) 0.30253(15) 0.14010(11) 0.0340 1.0000 Uani . . . . . . C3 C 0.93850(15) 0.28230(15) 0.20753(11) 0.0348 1.0000 Uani . . . . . . C4 C 0.84973(15) 0.26263(14) 0.21439(10) 0.0301 1.0000 Uani . . . . . . C5 C 0.79763(14) 0.26143(12) 0.15162(9) 0.0241 1.0000 Uani . . . . . . C6 C 0.94367(14) 0.32949(15) 0.00508(11) 0.0334 1.0000 Uani . . . . . . C7 C 1.01892(15) 0.36355(16) -0.01820(12) 0.0373 1.0000 Uani . . . . . . C8 C 1.03093(14) 0.39528(16) -0.09320(12) 0.0362 1.0000 Uani . . . . . . C9 C 1.09857(16) 0.45362(17) -0.11155(13) 0.0414 1.0000 Uani . . . . . . C10 C 1.10445(15) 0.49068(16) -0.18071(12) 0.0384 1.0000 Uani . . . . . . C11 C 1.04177(14) 0.47021(15) -0.23392(11) 0.0336 1.0000 Uani . . . . . . C12 C 0.97598(14) 0.40912(16) -0.21740(11) 0.0345 1.0000 Uani . . . . . . C13 C 0.97108(15) 0.37247(16) -0.14872(11) 0.0361 1.0000 Uani . . . . . . C14 C 1.12023(15) 0.53681(17) -0.33911(12) 0.0379 1.0000 Uani . . . . . . C15 C 1.19521(17) 0.4838(2) -0.33615(15) 0.0558 1.0000 Uani . . . . . . C16 C 1.27181(18) 0.5103(3) -0.37208(17) 0.0734 1.0000 Uani . . . . . . C17 C 1.27391(18) 0.5882(3) -0.41064(16) 0.0701 1.0000 Uani . . . . . . C18 C 1.19888(19) 0.6398(2) -0.41465(14) 0.0543 1.0000 Uani . . . . . . C19 C 1.12187(17) 0.61531(17) -0.37933(12) 0.0406 1.0000 Uani . . . . . . C20 C 0.95878(14) 0.53145(14) -0.33724(12) 0.0326 1.0000 Uani . . . . . . C21 C 0.89223(15) 0.57273(15) -0.29794(13) 0.0365 1.0000 Uani . . . . . . C22 C 0.81267(16) 0.59361(16) -0.33161(15) 0.0428 1.0000 Uani . . . . . . C23 C 0.79879(16) 0.57357(17) -0.40444(16) 0.0463 1.0000 Uani . . . . . . C24 C 0.86512(17) 0.53274(18) -0.44354(14) 0.0459 1.0000 Uani . . . . . . C25 C 0.94507(16) 0.51103(15) -0.41018(12) 0.0372 1.0000 Uani . . . . . . H21 H 1.0343 0.3157 0.1351 0.0433 1.0000 Uiso R . . . . . H31 H 0.9752 0.2812 0.2485 0.0430 1.0000 Uiso R . . . . . H41 H 0.8253 0.2499 0.2596 0.0378 1.0000 Uiso R . . . . . H61 H 0.8996 0.3214 -0.0310 0.0414 1.0000 Uiso R . . . . . H71 H 1.0676 0.3676 0.0148 0.0464 1.0000 Uiso R . . . . . H91 H 1.1418 0.4685 -0.0760 0.0492 1.0000 Uiso R . . . . . H101 H 1.1516 0.5301 -0.1919 0.0459 1.0000 Uiso R . . . . . H121 H 0.9350 0.3933 -0.2531 0.0431 1.0000 Uiso R . . . . . H131 H 0.9259 0.3307 -0.1388 0.0442 1.0000 Uiso R . . . . . H151 H 1.1934 0.4326 -0.3103 0.0652 1.0000 Uiso R . . . . . H161 H 1.3221 0.4749 -0.3697 0.0882 1.0000 Uiso R . . . . . H171 H 1.3260 0.6064 -0.4336 0.0844 1.0000 Uiso R . . . . . H181 H 1.1996 0.6920 -0.4416 0.0671 1.0000 Uiso R . . . . . H191 H 1.0712 0.6510 -0.3827 0.0523 1.0000 Uiso R . . . . . H211 H 0.9007 0.5862 -0.2479 0.0452 1.0000 Uiso R . . . . . H221 H 0.7673 0.6214 -0.3043 0.0544 1.0000 Uiso R . . . . . H231 H 0.7455 0.5871 -0.4271 0.0560 1.0000 Uiso R . . . . . H241 H 0.8561 0.5186 -0.4923 0.0540 1.0000 Uiso R . . . . . H251 H 0.9898 0.4833 -0.4364 0.0474 1.0000 Uiso R . . . . . P1 P 0.7500 0.7500 -0.12402(8) 0.0385 1.0000 Uani DS TU . 1 -1 . F1 F 0.7862(3) 0.6885(2) -0.1866(2) 0.1033 0.5000 Uani D U . 1 -1 . F2 F 0.8400(2) 0.80307(18) -0.1241(3) 0.0780 0.5000 Uani D U . 1 -1 . F3 F 0.7880(3) 0.6856(2) -0.0657(2) 0.0879 0.5000 Uani D U . 1 -1 . 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 0.03065(16) 0.03065(16) 0.01215(17) 0.0000 0.0000 0.0000 N1 0.0293(8) 0.0278(8) 0.0165(7) 0.0000(6) -0.0007(6) 0.0007(7) N2 0.0262(9) 0.0522(12) 0.0303(9) 0.0150(8) -0.0017(7) -0.0054(8) C1 0.0317(10) 0.0338(10) 0.0214(8) -0.0014(7) -0.0007(7) -0.0009(8) C2 0.0311(11) 0.0431(12) 0.0279(10) -0.0021(9) -0.0058(8) 0.0000(9) C3 0.0406(12) 0.0399(12) 0.0240(9) -0.0001(8) -0.0110(8) -0.0002(9) C4 0.0429(12) 0.0320(10) 0.0154(8) 0.0002(7) -0.0044(8) -0.0020(9) C5 0.0349(10) 0.0223(9) 0.0150(7) -0.0014(6) -0.0016(7) 0.0006(8) C6 0.0322(10) 0.0475(12) 0.0206(9) 0.0004(9) -0.0017(8) -0.0045(8) C7 0.0342(11) 0.0500(13) 0.0277(10) 0.0071(9) -0.0066(8) -0.0110(10) C8 0.0317(11) 0.0495(13) 0.0275(9) 0.0084(9) -0.0046(8) -0.0107(9) C9 0.0339(12) 0.0559(15) 0.0343(11) 0.0098(10) -0.0088(9) -0.0152(11) C10 0.0304(11) 0.0502(14) 0.0346(11) 0.0121(10) -0.0051(9) -0.0130(10) C11 0.0295(11) 0.0446(13) 0.0267(9) 0.0076(9) -0.0017(8) -0.0031(9) C12 0.0300(11) 0.0470(13) 0.0263(10) 0.0044(9) -0.0059(8) -0.0091(9) C13 0.0328(11) 0.0488(13) 0.0268(10) 0.0068(9) -0.0028(8) -0.0145(10) C14 0.0308(11) 0.0554(14) 0.0276(10) 0.0100(10) -0.0036(8) -0.0109(10) C15 0.0338(13) 0.087(2) 0.0469(14) 0.0286(15) 0.0004(11) -0.0001(13) C16 0.0282(13) 0.139(3) 0.0530(16) 0.033(2) 0.0010(12) 0.0007(16) C17 0.0343(14) 0.129(3) 0.0473(15) 0.0355(18) -0.0056(12) -0.0258(16) C18 0.0545(16) 0.0730(19) 0.0353(12) 0.0165(12) -0.0084(11) -0.0324(14) C19 0.0447(13) 0.0485(14) 0.0287(10) 0.0042(9) -0.0043(9) -0.0176(11) C20 0.0292(11) 0.0360(11) 0.0327(10) 0.0087(9) -0.0041(8) -0.0060(9) C21 0.0328(11) 0.0386(12) 0.0382(11) 0.0052(9) -0.0025(9) -0.0070(9) C22 0.0321(12) 0.0371(12) 0.0590(15) 0.0094(11) -0.0018(11) -0.0043(9) C23 0.0332(12) 0.0442(14) 0.0614(16) 0.0137(12) -0.0165(12) -0.0059(10) C24 0.0474(14) 0.0498(14) 0.0405(13) 0.0043(11) -0.0164(11) -0.0083(12) C25 0.0371(12) 0.0394(12) 0.0351(11) 0.0046(9) -0.0063(9) -0.0030(9) P1 0.0304(4) 0.0304(4) 0.0546(7) 0.0000 0.0000 0.0000 F1 0.142(5) 0.076(3) 0.091(3) -0.027(3) 0.039(4) 0.004(3) F2 0.0313(16) 0.0328(16) 0.170(5) -0.007(3) 0.015(3) -0.0029(13) F3 0.090(3) 0.068(3) 0.106(3) 0.036(2) -0.040(3) 0.008(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.08390(13) 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 . N1 4_565 2.0379(15) yes Cu1 . N1 5_655 2.0379(15) yes Cu1 . N1 8_645 2.0379(15) yes Cu1 . N1 . 2.0379(15) yes N1 . C1 . 1.351(3) yes N1 . C5 . 1.353(2) yes N2 . C11 . 1.418(3) yes N2 . C14 . 1.411(3) yes N2 . C20 . 1.426(3) yes C1 . C2 . 1.401(3) yes C1 . C6 . 1.462(3) yes C2 . C3 . 1.376(3) yes C2 . H21 . 0.948 no C3 . C4 . 1.380(3) yes C3 . H31 . 0.933 no C4 . C5 . 1.393(3) yes C4 . H41 . 0.926 no C5 . C5 5_655 1.481(4) yes C6 . C7 . 1.320(3) yes C6 . H61 . 0.946 no C7 . C8 . 1.465(3) yes C7 . H71 . 0.954 no C8 . C9 . 1.392(3) yes C8 . C13 . 1.404(3) yes C9 . C10 . 1.387(3) yes C9 . H91 . 0.949 no C10 . C11 . 1.393(3) yes C10 . H101 . 0.952 no C11 . C12 . 1.391(3) yes C12 . C13 . 1.375(3) yes C12 . H121 . 0.931 no C13 . H131 . 0.948 no C14 . C15 . 1.390(4) yes C14 . C19 . 1.397(3) yes C15 . C16 . 1.391(4) yes C15 . H151 . 0.909 no C16 . C17 . 1.373(5) yes C16 . H161 . 0.930 no C17 . C18 . 1.379(5) yes C17 . H171 . 0.934 no C18 . C19 . 1.382(3) yes C18 . H181 . 0.931 no C19 . H191 . 0.939 no C20 . C21 . 1.385(3) yes C20 . C25 . 1.385(3) yes C21 . C22 . 1.388(3) yes C21 . H211 . 0.947 no C22 . C23 . 1.383(4) yes C22 . H221 . 0.947 no C23 . C24 . 1.378(4) yes C23 . H231 . 0.929 no C24 . C25 . 1.394(3) yes C24 . H241 . 0.928 no C25 . H251 . 0.930 no P1 . F1 . 1.574(4) yes P1 . F2 . 1.580(3) yes P1 . F3 . 1.555(3) yes 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 N1 4_565 Cu1 . N1 5_655 125.64(5) yes N1 4_565 Cu1 . N1 8_645 80.48(9) yes N1 5_655 Cu1 . N1 8_645 125.64(5) yes N1 4_565 Cu1 . N1 . 125.64(5) yes N1 5_655 Cu1 . N1 . 80.48(9) yes N1 8_645 Cu1 . N1 . 125.64(5) yes Cu1 . N1 . C1 . 125.25(12) yes Cu1 . N1 . C5 . 114.21(13) yes C1 . N1 . C5 . 119.66(16) yes C11 . N2 . C14 . 122.07(18) yes C11 . N2 . C20 . 119.02(17) yes C14 . N2 . C20 . 118.82(17) yes N1 . C1 . C2 . 120.70(18) yes N1 . C1 . C6 . 113.90(17) yes C2 . C1 . C6 . 125.36(19) yes C1 . C2 . C3 . 119.2(2) yes C1 . C2 . H21 . 120.4 no C3 . C2 . H21 . 120.4 no C2 . C3 . C4 . 120.10(19) yes C2 . C3 . H31 . 119.7 no C4 . C3 . H31 . 120.2 no C3 . C4 . C5 . 118.55(18) yes C3 . C4 . H41 . 120.9 no C5 . C4 . H41 . 120.5 no C5 5_655 C5 . C4 . 123.58(12) yes C5 5_655 C5 . N1 . 114.76(11) yes C4 . C5 . N1 . 121.66(19) yes C1 . C6 . C7 . 129.5(2) yes C1 . C6 . H61 . 114.9 no C7 . C6 . H61 . 115.6 no C6 . C7 . C8 . 122.5(2) yes C6 . C7 . H71 . 119.1 no C8 . C7 . H71 . 118.4 no C7 . C8 . C9 . 121.65(19) yes C7 . C8 . C13 . 121.17(19) yes C9 . C8 . C13 . 117.06(19) yes C8 . C9 . C10 . 121.6(2) yes C8 . C9 . H91 . 119.4 no C10 . C9 . H91 . 119.0 no C9 . C10 . C11 . 120.3(2) yes C9 . C10 . H101 . 119.8 no C11 . C10 . H101 . 119.9 no N2 . C11 . C10 . 122.27(19) yes N2 . C11 . C12 . 118.88(19) yes C10 . C11 . C12 . 118.83(19) yes C11 . C12 . C13 . 120.32(19) yes C11 . C12 . H121 . 119.6 no C13 . C12 . H121 . 120.1 no C8 . C13 . C12 . 121.8(2) yes C8 . C13 . H131 . 119.3 no C12 . C13 . H131 . 118.9 no N2 . C14 . C15 . 120.8(2) yes N2 . C14 . C19 . 119.4(2) yes C15 . C14 . C19 . 119.8(2) yes C14 . C15 . C16 . 119.7(3) yes C14 . C15 . H151 . 119.2 no C16 . C15 . H151 . 121.1 no C15 . C16 . C17 . 120.6(3) yes C15 . C16 . H161 . 119.5 no C17 . C16 . H161 . 119.9 no C16 . C17 . C18 . 119.6(2) yes C16 . C17 . H171 . 120.2 no C18 . C17 . H171 . 120.3 no C17 . C18 . C19 . 121.1(3) yes C17 . C18 . H181 . 119.9 no C19 . C18 . H181 . 119.0 no C14 . C19 . C18 . 119.2(3) yes C14 . C19 . H191 . 120.6 no C18 . C19 . H191 . 120.2 no N2 . C20 . C21 . 120.6(2) yes N2 . C20 . C25 . 119.9(2) yes C21 . C20 . C25 . 119.5(2) yes C20 . C21 . C22 . 120.1(2) yes C20 . C21 . H211 . 120.0 no C22 . C21 . H211 . 119.9 no C21 . C22 . C23 . 120.6(2) yes C21 . C22 . H221 . 119.6 no C23 . C22 . H221 . 119.7 no C22 . C23 . C24 . 119.2(2) yes C22 . C23 . H231 . 120.9 no C24 . C23 . H231 . 119.9 no C23 . C24 . C25 . 120.6(2) yes C23 . C24 . H241 . 119.7 no C25 . C24 . H241 . 119.7 no C24 . C25 . C20 . 120.0(2) yes C24 . C25 . H251 . 120.7 no C20 . C25 . H251 . 119.3 no F1 . P1 . F2 . 90.001(10) yes F1 . P1 . F3 . 89.997(10) yes F2 . P1 . F3 . 90.002(10) yes _iucr_refine_instruction_details_constraints ; # # Punched on 04/01/12 at 15:37:58 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 04/01/12 at 15:37:58 # #LIST 16 REM PF6 DIST 0.0, 0.01 = MEAN CONT P(1) TO F(1) P(1) TO F(2) P(1) TO F(3) ANGLE 90, 0.01 = CONT F(1) TO P(1) TO F(2) F(1) TO P(1) TO F(3) CONT F(2) TO P(1) TO F(3) VIBRA 0.0,0.01 = CONT P(1) TO F(1) P(1) TO F(2) P(1) TO F(3) U(IJ)'S 0.0,0.02 = CONT P(1) TO F(1) P(1) TO F(2) P(1) TO F(3) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM SHIFTLIMIT START (DO NOT REMOVE THIS LINE) REM REM SHIFTLIMIT END (DO NOT REMOVE THIS LINE) END ; # Attachment '- Cu_complex.cif' data_Cu_complex _database_code_depnum_ccdc_archive 'CCDC 885555' #TrackingRef '- Cu_complex.cif' _audit_creation_date 12-01-03 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'bb164a_123k_0ma in P4/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 15.1209(2) _cell_length_b 15.1209(2) _cell_length_c 18.2971(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4183.48(12) _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P 4/n' _symmetry_space_group_name_Hall '-P 4a' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -y+1/2,x,z y+1/2,-x,-z -x+1/2,-y+1/2,z x+1/2,y+1/2,-z y,-x+1/2,z -y,x+1/2,-z 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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 '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' _cell_formula_units_Z 2 # Given Formula = C101 H84 Cu1 F6 N8 O3 P1 # Dc = 1.32 Fooo = 1720.00 Mu = 3.52 M = 416.58 # Found Formula = C101 H76 Cu1 F6 N8 O3 P1 # Dc = 1.32 FOOO = 1720.00 Mu = 3.52 M = 414.57 _chemical_formula_sum 'C101 H84 Cu1 F6 N8 O3 P1' _chemical_formula_moiety 'C100 H76 Cu1 N8 O3, F6 P, C H4 O, 2(H2 O)' _chemical_compound_source ? _chemical_formula_weight 1666.32 _cell_measurement_reflns_used 8009 _cell_measurement_theta_min 4 _cell_measurement_theta_max 32 _cell_measurement_temperature 123 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_max 0.210 _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 0.352 # Sheldrick geometric approximatio 0.94 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 123 _diffrn_reflns_number 49103 _reflns_number_total 7090 _diffrn_reflns_av_R_equivalents 0.062 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 7090 # Theoretical number of reflections is about 14133 _diffrn_reflns_theta_min 1.747 _diffrn_reflns_theta_max 31.714 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 31.714 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -15 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 27 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.41 _refine_diff_density_max 0.64 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 3509 _refine_ls_number_restraints 513 _refine_ls_number_parameters 321 _oxford_refine_ls_R_factor_ref 0.0453 _refine_ls_wR_factor_ref 0.0472 _refine_ls_goodness_of_fit_ref 1.0460 _refine_ls_shift/su_max 0.0084530 _refine_ls_shift/su_mean 0.0003181 # The values computed from all data _oxford_reflns_number_all 7074 _refine_ls_R_factor_all 0.0965 _refine_ls_wR_factor_all 0.1233 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4386 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_gt 0.0533 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _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: 0.231 0.211 0.800E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. ; _vrf_PLAT051_I ; PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 16.88 Perc. RESPONSE: Checkcif seems not to recognize that P1 is on a special position. ; # end Validation Reply Form # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 Cu1 Cu 0.7500 0.2500 0.0000 0.0245 1.0000 Uani S T . . . . N1 N 0.83173(10) 0.28017(10) 0.08504(8) 0.0248 1.0000 Uani . . . . . . N2 N 1.04150(11) 0.51116(13) -0.30367(9) 0.0365 1.0000 Uani . . . . . . C1 C 0.91776(13) 0.30294(13) 0.07889(10) 0.0291 1.0000 Uani . . . . . . C2 C 0.97336(14) 0.30262(14) 0.14011(11) 0.0344 1.0000 Uani . . . . . . C3 C 0.93844(14) 0.28227(14) 0.20756(11) 0.0352 1.0000 Uani . . . . . . C4 C 0.84984(14) 0.26269(13) 0.21434(9) 0.0304 1.0000 Uani . . . . . . C5 C 0.79754(13) 0.26145(11) 0.15167(9) 0.0241 1.0000 Uani . . . . . . C6 C 0.94357(13) 0.32948(14) 0.00508(11) 0.0337 1.0000 Uani . . . . . . C7 C 1.01895(14) 0.36353(15) -0.01821(11) 0.0375 1.0000 Uani . . . . . . C8 C 1.03095(14) 0.39523(15) -0.09324(11) 0.0363 1.0000 Uani . . . . . . C9 C 1.09858(15) 0.45353(16) -0.11173(12) 0.0414 1.0000 Uani . . . . . . C10 C 1.10455(14) 0.49068(15) -0.18066(12) 0.0386 1.0000 Uani . . . . . . C11 C 1.04175(13) 0.47010(14) -0.23389(11) 0.0335 1.0000 Uani . . . . . . C12 C 0.97604(13) 0.40921(15) -0.21738(11) 0.0348 1.0000 Uani . . . . . . C13 C 0.97115(14) 0.37246(15) -0.14876(11) 0.0366 1.0000 Uani . . . . . . C14 C 1.12019(14) 0.53680(16) -0.33908(11) 0.0382 1.0000 Uani . . . . . . C15 C 1.19521(16) 0.4839(2) -0.33607(14) 0.0560 1.0000 Uani . . . . . . C16 C 1.27178(17) 0.5104(3) -0.37197(15) 0.0733 1.0000 Uani . . . . . . C17 C 1.27399(17) 0.5882(2) -0.41062(15) 0.0705 1.0000 Uani . . . . . . C18 C 1.19879(17) 0.63966(19) -0.41469(13) 0.0543 1.0000 Uani . . . . . . C19 C 1.12187(16) 0.61537(16) -0.37926(11) 0.0408 1.0000 Uani . . . . . . C20 C 0.95884(13) 0.53137(14) -0.33715(11) 0.0328 1.0000 Uani . . . . . . C21 C 0.89226(14) 0.57260(14) -0.29797(12) 0.0367 1.0000 Uani . . . . . . C22 C 0.81259(15) 0.59354(15) -0.33164(14) 0.0427 1.0000 Uani . . . . . . C23 C 0.79854(15) 0.57346(15) -0.40444(15) 0.0463 1.0000 Uani . . . . . . C24 C 0.86524(16) 0.53280(16) -0.44363(13) 0.0462 1.0000 Uani . . . . . . C25 C 0.94514(14) 0.51098(14) -0.41017(12) 0.0374 1.0000 Uani . . . . . . H21 H 1.0344 0.3158 0.1351 0.0433 1.0000 Uiso R . . . . . H31 H 0.9752 0.2812 0.2485 0.0430 1.0000 Uiso R . . . . . H41 H 0.8254 0.2500 0.2595 0.0378 1.0000 Uiso R . . . . . H61 H 0.8995 0.3214 -0.0310 0.0414 1.0000 Uiso R . . . . . H71 H 1.0676 0.3676 0.0148 0.0464 1.0000 Uiso R . . . . . H91 H 1.1418 0.4684 -0.0762 0.0492 1.0000 Uiso R . . . . . H101 H 1.1517 0.5301 -0.1918 0.0459 1.0000 Uiso R . . . . . H121 H 0.9351 0.3934 -0.2530 0.0431 1.0000 Uiso R . . . . . H131 H 0.9259 0.3307 -0.1388 0.0442 1.0000 Uiso R . . . . . H151 H 1.1934 0.4327 -0.3102 0.0652 1.0000 Uiso R . . . . . H161 H 1.3220 0.4750 -0.3696 0.0882 1.0000 Uiso R . . . . . H171 H 1.3261 0.6064 -0.4335 0.0844 1.0000 Uiso R . . . . . H181 H 1.1995 0.6919 -0.4416 0.0671 1.0000 Uiso R . . . . . H191 H 1.0712 0.6511 -0.3826 0.0523 1.0000 Uiso R . . . . . H211 H 0.9008 0.5860 -0.2479 0.0452 1.0000 Uiso R . . . . . H221 H 0.7672 0.6213 -0.3043 0.0544 1.0000 Uiso R . . . . . H231 H 0.7452 0.5870 -0.4271 0.0560 1.0000 Uiso R . . . . . H241 H 0.8562 0.5186 -0.4924 0.0540 1.0000 Uiso R . . . . . H251 H 0.9899 0.4833 -0.4364 0.0474 1.0000 Uiso R . . . . . P1 P 0.7500 0.7500 -0.12417(7) 0.0383 1.0000 Uani DS TU . 1 -1 . F1 F 0.7858(2) 0.6887(2) -0.1869(2) 0.1030 0.5000 Uani D U . 1 -1 . F2 F 0.84000(17) 0.80321(16) -0.1246(2) 0.0791 0.5000 Uani D U . 1 -1 . F3 F 0.7886(2) 0.68536(18) -0.0660(2) 0.0890 0.5000 Uani D U . 1 -1 . O1 O 0.7508(8) 0.7502(9) 0.09193(18) 0.0396 0.2500 Uani . U . . . . C26 C 0.7612(6) 0.7984(5) 0.1953(5) 0.0496 0.2500 Uani . U . 2 -2 . O2 O 0.7258(4) 0.7406(8) 0.2487(3) 0.0599 0.2500 Uani . U . 2 -2 . O3 O 0.7007(7) 0.7137(7) 0.4324(6) 0.0564 0.1250 Uani . U . 3 -3 . O4 O 0.6957(7) 0.6466(7) 0.4174(6) 0.0508 0.1250 Uani . U . 3 -3 . 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 0.03069(14) 0.03069(14) 0.01220(16) 0.0000 0.0000 0.0000 N1 0.0298(5) 0.0277(6) 0.0168(5) 0.0001(5) -0.0004(5) 0.0009(5) N2 0.0268(5) 0.0527(7) 0.0300(6) 0.0143(6) -0.0018(5) -0.0056(6) C1 0.0311(5) 0.0341(7) 0.0220(6) -0.0011(6) -0.0007(6) -0.0011(6) C2 0.0318(6) 0.0434(7) 0.0281(6) -0.0023(6) -0.0060(6) 0.0000(6) C3 0.0416(6) 0.0398(7) 0.0241(6) 0.0005(6) -0.0111(6) -0.0002(6) C4 0.0441(6) 0.0318(7) 0.0155(6) 0.0000(6) -0.0039(6) -0.0015(6) C5 0.0348(5) 0.0225(6) 0.0150(5) -0.0017(5) -0.0017(5) 0.0006(6) C6 0.0327(5) 0.0472(7) 0.0213(6) 0.0005(6) -0.0017(6) -0.0047(6) C7 0.0345(6) 0.0502(8) 0.0278(7) 0.0074(6) -0.0071(6) -0.0107(7) C8 0.0318(6) 0.0492(7) 0.0279(6) 0.0084(6) -0.0043(6) -0.0102(6) C9 0.0336(6) 0.0561(8) 0.0345(7) 0.0098(7) -0.0093(6) -0.0148(7) C10 0.0303(6) 0.0508(8) 0.0346(7) 0.0126(7) -0.0048(6) -0.0135(7) C11 0.0296(6) 0.0441(7) 0.0267(6) 0.0080(6) -0.0014(6) -0.0026(6) C12 0.0303(6) 0.0476(7) 0.0264(6) 0.0048(6) -0.0059(6) -0.0099(6) C13 0.0332(6) 0.0489(7) 0.0278(7) 0.0069(6) -0.0032(6) -0.0148(6) C14 0.0311(6) 0.0560(8) 0.0275(6) 0.0098(7) -0.0038(6) -0.0104(7) C15 0.0340(6) 0.0874(8) 0.0465(8) 0.0277(8) 0.0009(7) 0.0005(7) C16 0.0292(6) 0.1377(9) 0.0531(8) 0.0331(8) 0.0007(7) 0.0007(8) C17 0.0350(6) 0.1291(9) 0.0474(8) 0.0353(8) -0.0057(7) -0.0256(8) C18 0.0549(6) 0.0734(8) 0.0345(7) 0.0162(7) -0.0083(7) -0.0330(7) C19 0.0452(6) 0.0483(8) 0.0288(7) 0.0041(7) -0.0044(6) -0.0171(7) C20 0.0294(6) 0.0360(7) 0.0330(7) 0.0084(6) -0.0044(6) -0.0058(6) C21 0.0324(6) 0.0399(7) 0.0379(7) 0.0056(7) -0.0018(6) -0.0067(6) C22 0.0332(6) 0.0366(7) 0.0583(8) 0.0090(7) -0.0012(7) -0.0039(6) C23 0.0328(6) 0.0441(8) 0.0618(8) 0.0138(7) -0.0163(7) -0.0059(7) C24 0.0472(6) 0.0503(8) 0.0411(7) 0.0047(7) -0.0159(7) -0.0088(7) C25 0.0369(6) 0.0402(7) 0.0352(7) 0.0044(7) -0.0061(6) -0.0029(7) P1 0.0306(3) 0.0306(3) 0.0539(6) 0.0000 0.0000 0.0000 F1 0.1427(7) 0.0782(9) 0.0883(9) -0.0271(9) 0.0394(9) 0.0041(9) F2 0.0340(6) 0.0323(8) 0.1710(9) -0.0067(9) 0.0190(9) -0.0032(8) F3 0.0891(6) 0.0691(9) 0.1087(9) 0.0383(8) -0.0387(9) 0.0108(8) O1 0.0481(6) 0.0366(9) 0.0341(8) 0.0068(9) 0.0258(9) 0.0036(9) C26 0.0635(7) 0.0249(9) 0.0604(9) -0.0092(9) 0.0250(9) -0.0100(9) O2 0.0539(7) 0.0635(9) 0.0623(9) 0.0118(9) 0.0499(9) 0.0067(9) O3 0.0585(7) 0.0635(9) 0.0471(9) 0.0009(9) 0.0311(9) -0.0117(9) O4 0.0647(7) 0.0518(9) 0.0361(9) 0.0132(9) 0.0199(9) 0.0213(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.08417(11) 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 . N1 4_565 2.0386(15) yes Cu1 . N1 8_645 2.0386(15) yes Cu1 . N1 5_655 2.0386(15) yes Cu1 . N1 . 2.0386(15) yes N1 . C1 . 1.350(2) yes N1 . C5 . 1.354(2) yes N2 . C11 . 1.420(3) yes N2 . C14 . 1.409(3) yes N2 . C20 . 1.425(3) yes C1 . C2 . 1.401(3) yes C1 . C6 . 1.462(3) yes C2 . C3 . 1.377(3) yes C2 . H21 . 0.948 no C3 . C4 . 1.378(3) yes C3 . H31 . 0.933 no C4 . C5 . 1.393(2) yes C4 . H41 . 0.926 no C5 . C5 5_655 1.479(4) yes C6 . C7 . 1.321(3) yes C6 . H61 . 0.946 no C7 . C8 . 1.465(3) yes C7 . H71 . 0.954 no C8 . C9 . 1.392(3) yes C8 . C13 . 1.403(3) yes C9 . C10 . 1.383(3) yes C9 . H91 . 0.949 no C10 . C11 . 1.395(3) yes C10 . H101 . 0.952 no C11 . C12 . 1.388(3) yes C12 . C13 . 1.375(3) yes C12 . H121 . 0.931 no C13 . H131 . 0.948 no C14 . C15 . 1.389(3) yes C14 . C19 . 1.397(3) yes C15 . C16 . 1.390(3) yes C15 . H151 . 0.909 no C16 . C17 . 1.373(4) yes C16 . H161 . 0.930 no C17 . C18 . 1.380(4) yes C17 . H171 . 0.934 no C18 . C19 . 1.381(3) yes C18 . H181 . 0.931 no C19 . H191 . 0.939 no C20 . C21 . 1.384(3) yes C20 . C25 . 1.387(3) yes C21 . C22 . 1.389(3) yes C21 . H211 . 0.947 no C22 . C23 . 1.383(4) yes C22 . H221 . 0.947 no C23 . C24 . 1.382(4) yes C23 . H231 . 0.929 no C24 . C25 . 1.394(3) yes C24 . H241 . 0.928 no C25 . H251 . 0.930 no P1 . F1 . 1.570(4) yes P1 . F2 . 1.581(3) yes P1 . F3 . 1.559(3) yes C26 . O2 . 1.416(10) yes O3 . O4 . 1.054(14) yes 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 N1 4_565 Cu1 . N1 8_645 80.50(8) yes N1 4_565 Cu1 . N1 5_655 125.63(5) yes N1 8_645 Cu1 . N1 5_655 125.63(5) yes N1 4_565 Cu1 . N1 . 125.63(5) yes N1 8_645 Cu1 . N1 . 125.63(5) yes N1 5_655 Cu1 . N1 . 80.50(8) yes Cu1 . N1 . C1 . 125.27(12) yes Cu1 . N1 . C5 . 114.14(12) yes C1 . N1 . C5 . 119.73(15) yes C11 . N2 . C14 . 122.11(17) yes C11 . N2 . C20 . 118.86(16) yes C14 . N2 . C20 . 118.94(16) yes N1 . C1 . C2 . 120.72(17) yes N1 . C1 . C6 . 113.83(16) yes C2 . C1 . C6 . 125.41(18) yes C1 . C2 . C3 . 119.17(19) yes C1 . C2 . H21 . 120.4 no C3 . C2 . H21 . 120.4 no C2 . C3 . C4 . 120.11(18) yes C2 . C3 . H31 . 119.7 no C4 . C3 . H31 . 120.2 no C3 . C4 . C5 . 118.74(17) yes C3 . C4 . H41 . 120.9 no C5 . C4 . H41 . 120.4 no C5 5_655 C5 . C4 . 123.72(12) yes C5 5_655 C5 . N1 . 114.84(11) yes C4 . C5 . N1 . 121.44(18) yes C1 . C6 . C7 . 129.43(19) yes C1 . C6 . H61 . 114.9 no C7 . C6 . H61 . 115.6 no C6 . C7 . C8 . 122.44(19) yes C6 . C7 . H71 . 119.1 no C8 . C7 . H71 . 118.4 no C7 . C8 . C9 . 121.73(18) yes C7 . C8 . C13 . 121.21(18) yes C9 . C8 . C13 . 116.94(18) yes C8 . C9 . C10 . 121.78(19) yes C8 . C9 . H91 . 119.3 no C10 . C9 . H91 . 118.9 no C9 . C10 . C11 . 120.09(19) yes C9 . C10 . H101 . 119.9 no C11 . C10 . H101 . 120.0 no N2 . C11 . C10 . 122.14(18) yes N2 . C11 . C12 . 118.95(18) yes C10 . C11 . C12 . 118.89(18) yes C11 . C12 . C13 . 120.36(18) yes C11 . C12 . H121 . 119.6 no C13 . C12 . H121 . 120.0 no C8 . C13 . C12 . 121.82(19) yes C8 . C13 . H131 . 119.3 no C12 . C13 . H131 . 118.9 no N2 . C14 . C15 . 120.9(2) yes N2 . C14 . C19 . 119.4(2) yes C15 . C14 . C19 . 119.7(2) yes C14 . C15 . C16 . 119.7(3) yes C14 . C15 . H151 . 119.2 no C16 . C15 . H151 . 121.1 no C15 . C16 . C17 . 120.7(3) yes C15 . C16 . H161 . 119.5 no C17 . C16 . H161 . 119.8 no C16 . C17 . C18 . 119.4(2) yes C16 . C17 . H171 . 120.3 no C18 . C17 . H171 . 120.3 no C17 . C18 . C19 . 121.2(2) yes C17 . C18 . H181 . 119.8 no C19 . C18 . H181 . 118.9 no C14 . C19 . C18 . 119.2(2) yes C14 . C19 . H191 . 120.6 no C18 . C19 . H191 . 120.2 no N2 . C20 . C21 . 120.79(19) yes N2 . C20 . C25 . 119.84(19) yes C21 . C20 . C25 . 119.37(19) yes C20 . C21 . C22 . 120.2(2) yes C20 . C21 . H211 . 119.9 no C22 . C21 . H211 . 119.8 no C21 . C22 . C23 . 120.7(2) yes C21 . C22 . H221 . 119.7 no C23 . C22 . H221 . 119.6 no C22 . C23 . C24 . 119.0(2) yes C22 . C23 . H231 . 121.0 no C24 . C23 . H231 . 120.0 no C23 . C24 . C25 . 120.7(2) yes C23 . C24 . H241 . 119.6 no C25 . C24 . H241 . 119.7 no C24 . C25 . C20 . 120.0(2) yes C24 . C25 . H251 . 120.7 no C20 . C25 . H251 . 119.3 no F1 . P1 . F2 . 90.000(10) yes F1 . P1 . F3 . 89.998(10) yes F2 . P1 . F3 . 90.002(10) yes _iucr_refine_instruction_details_constraints ; # # Punched on 03/01/12 at 20:50:13 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 03/01/12 at 20:50:13 # #LIST 16 REM PF6 DIST 0.0, 0.01 = MEAN CONT P(1) TO F(1) P(1) TO F(2) P(1) TO F(3) ANGLE 90, 0.01 = CONT F(1) TO P(1) TO F(2) F(1) TO P(1) TO F(3) CONT F(2) TO P(1) TO F(3) VIBRA 0.0,0.01 = CONT P(1) TO F(1) P(1) TO F(2) P(1) TO F(3) U(IJ)'S 0.0,0.02 = CONT P(1) TO F(1) P(1) TO F(2) P(1) TO F(3) REM SOLVENT VIBRA 0.0,0.01 = CONT O(1) TO C(26) O(1) TO O(2) O(1) TO O(3) O(1) TO O(4) CONT C(26) TO O(2) C(26) TO O(3) C(26) TO O(4) CONT O(2) TO O(3) O(2) TO O(4) CONT O(3) TO O(4) U(IJ)'S 0.0,0.02 = CONT O(1) TO C(26) O(1) TO O(2) O(1) TO O(3) O(1) TO O(4) CONT C(26) TO O(2) C(26) TO O(3) C(26) TO O(4) CONT O(2) TO O(3) O(2) TO O(4) CONT O(3) TO O(4) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM SHIFTLIMIT START (DO NOT REMOVE THIS LINE) LIMIT 0.00100000 U[ISO] LIMIT 0.00100000 X LIMIT 0.00100000 Y LIMIT 0.00100000 Z LIMIT 0.00100000 U[11] LIMIT 0.00100000 U[22] LIMIT 0.00100000 U[33] LIMIT 0.00100000 U[12] LIMIT 0.00100000 U[13] LIMIT 0.00100000 U[23] LIMIT 0.00100000 OCC REM SHIFTLIMIT END (DO NOT REMOVE THIS LINE) END ; # Attachment '- Ligand.cif' data_Ligand _database_code_depnum_ccdc_archive 'CCDC 885556' #TrackingRef '- Ligand.cif' _audit_creation_date 11-12-10 _audit_creation_method CRYSTALS_ver_14.23 _oxford_structure_analysis_title 'uba15a in Pbca' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.9360(3) _cell_length_b 15.3904(5) _cell_length_c 26.8164(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3688.0(2) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 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 0.0181 0.0091 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 0.0311 0.0180 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' _cell_formula_units_Z 4 # Given Formula = C40 H70 N2 # Dc = 1.04 Fooo = 1464.00 Mu = 4.33 M = 289.50 # Found Formula = C50 H38 N4 # Dc = 1.25 FOOO = 1464.00 Mu = 5.65 M = 347.44 _chemical_formula_sum 'C50 H38 N4' _chemical_formula_moiety 'C50 H38 N4' _chemical_compound_source ? _chemical_formula_weight 694.88 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.020 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_max 0.220 _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 0.565 # Sheldrick geometric approximatio 0.95 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 35364 _reflns_number_total 3377 _diffrn_reflns_av_R_equivalents 0.068 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3377 # Theoretical number of reflections is about 6786 _diffrn_reflns_theta_min 3.296 _diffrn_reflns_theta_max 68.471 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 67.102 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _reflns_limit_h_min 0 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 32 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.28 _refine_diff_density_max 0.22 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 2724 _refine_ls_number_restraints 0 _refine_ls_number_parameters 244 _oxford_refine_ls_R_factor_ref 0.0478 _refine_ls_wR_factor_ref 0.0384 _refine_ls_goodness_of_fit_ref 1.0410 _refine_ls_shift/su_max 0.0005364 _refine_ls_shift/su_mean 0.0000435 # The values computed from all data _oxford_reflns_number_all 3362 _refine_ls_R_factor_all 0.0629 _refine_ls_wR_factor_all 0.0554 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2724 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_gt 0.0384 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _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: 0.284 0.297 0.145 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Sheldrick, G. M. (2008). Acta Cryst A64, 112-122. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 N1 N 0.07390(14) 0.60158(8) 0.02224(4) 0.0193 1.0000 Uani . . . . . . N2 N 0.04242(15) 1.07410(8) 0.18803(4) 0.0218 1.0000 Uani . . . . . . C1 C 0.07132(16) 0.52497(9) -0.00168(5) 0.0184 1.0000 Uani . . . . . . C2 C 0.19393(17) 0.49296(10) -0.02813(6) 0.0210 1.0000 Uani . . . . . . C3 C 0.32298(17) 0.54241(10) -0.02990(6) 0.0230 1.0000 Uani . . . . . . C4 C 0.32727(17) 0.62120(11) -0.00522(6) 0.0225 1.0000 Uani . . . . . . C5 C 0.20075(16) 0.64932(10) 0.02059(5) 0.0198 1.0000 Uani . . . . . . C6 C 0.20186(18) 0.73245(10) 0.04735(6) 0.0215 1.0000 Uani . . . . . . C7 C 0.09260(16) 0.75812(10) 0.07808(5) 0.0206 1.0000 Uani . . . . . . C8 C 0.08505(16) 0.83924(10) 0.10623(5) 0.0197 1.0000 Uani . . . . . . C9 C 0.16635(16) 0.91379(10) 0.09309(6) 0.0207 1.0000 Uani . . . . . . C10 C 0.15263(17) 0.99023(10) 0.11983(6) 0.0205 1.0000 Uani . . . . . . C11 C 0.05878(17) 0.99458(10) 0.16138(5) 0.0199 1.0000 Uani . . . . . . C12 C -0.01945(17) 0.92020(10) 0.17559(6) 0.0224 1.0000 Uani . . . . . . C13 C -0.00841(18) 0.84440(10) 0.14798(6) 0.0222 1.0000 Uani . . . . . . C14 C 0.03326(17) 1.07222(10) 0.24081(5) 0.0207 1.0000 Uani . . . . . . C15 C 0.12544(17) 1.01651(10) 0.26805(6) 0.0219 1.0000 Uani . . . . . . C16 C 0.11676(17) 1.01425(11) 0.31953(6) 0.0236 1.0000 Uani . . . . . . C17 C 0.01724(18) 1.06739(11) 0.34476(6) 0.0252 1.0000 Uani . . . . . . C18 C -0.07468(18) 1.12291(11) 0.31781(6) 0.0242 1.0000 Uani . . . . . . C19 C -0.06723(17) 1.12540(10) 0.26627(6) 0.0226 1.0000 Uani . . . . . . C20 C 0.00931(17) 1.15147(10) 0.16156(5) 0.0210 1.0000 Uani . . . . . . C21 C 0.06668(17) 1.23103(10) 0.17758(6) 0.0236 1.0000 Uani . . . . . . C22 C 0.03248(18) 1.30668(10) 0.15206(6) 0.0272 1.0000 Uani . . . . . . C23 C -0.05775(19) 1.30425(11) 0.11006(6) 0.0301 1.0000 Uani . . . . . . C24 C -0.1142(2) 1.22517(11) 0.09385(6) 0.0295 1.0000 Uani . . . . . . C25 C -0.08171(18) 1.14953(11) 0.11950(6) 0.0251 1.0000 Uani . . . . . . H21 H 0.1865 0.4378 -0.0448 0.0242 1.0000 Uiso R . . . . . H31 H 0.4095 0.5237 -0.0483 0.0277 1.0000 Uiso R . . . . . H41 H 0.4157 0.6548 -0.0063 0.0267 1.0000 Uiso R . . . . . H61 H 0.2894 0.7700 0.0426 0.0264 1.0000 Uiso R . . . . . H71 H 0.0103 0.7200 0.0831 0.0244 1.0000 Uiso R . . . . . H91 H 0.2302 0.9108 0.0643 0.0255 1.0000 Uiso R . . . . . H101 H 0.2068 1.0424 0.1099 0.0243 1.0000 Uiso R . . . . . H121 H -0.0842 0.9213 0.2047 0.0268 1.0000 Uiso R . . . . . H131 H -0.0662 0.7947 0.1575 0.0269 1.0000 Uiso R . . . . . H151 H 0.1961 0.9800 0.2507 0.0252 1.0000 Uiso R . . . . . H161 H 0.1796 0.9755 0.3378 0.0290 1.0000 Uiso R . . . . . H171 H 0.0104 1.0657 0.3805 0.0284 1.0000 Uiso R . . . . . H181 H -0.1429 1.1600 0.3355 0.0280 1.0000 Uiso R . . . . . H191 H -0.1298 1.1643 0.2479 0.0270 1.0000 Uiso R . . . . . H211 H 0.1275 1.2320 0.2063 0.0281 1.0000 Uiso R . . . . . H221 H 0.0701 1.3617 0.1634 0.0328 1.0000 Uiso R . . . . . H231 H -0.0805 1.3555 0.0920 0.0353 1.0000 Uiso R . . . . . H241 H -0.1757 1.2237 0.0646 0.0334 1.0000 Uiso R . . . . . H251 H -0.1213 1.0942 0.1086 0.0291 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 N1 0.0194(6) 0.0215(7) 0.0168(6) 0.0001(5) -0.0013(5) 0.0003(5) N2 0.0292(7) 0.0175(7) 0.0187(6) -0.0007(5) -0.0011(5) 0.0031(6) C1 0.0207(7) 0.0201(8) 0.0143(7) 0.0007(6) -0.0017(6) 0.0010(6) C2 0.0214(7) 0.0219(8) 0.0197(7) -0.0011(6) 0.0002(6) 0.0005(6) C3 0.0195(8) 0.0271(8) 0.0223(8) -0.0031(7) 0.0030(6) 0.0018(6) C4 0.0195(8) 0.0258(8) 0.0223(8) -0.0005(7) 0.0010(6) -0.0029(6) C5 0.0195(7) 0.0229(8) 0.0171(7) 0.0022(6) -0.0019(6) -0.0004(6) C6 0.0220(8) 0.0212(8) 0.0213(8) 0.0000(7) -0.0020(6) -0.0015(7) C7 0.0205(7) 0.0210(8) 0.0202(8) 0.0013(6) -0.0023(6) -0.0012(6) C8 0.0181(7) 0.0208(8) 0.0202(7) -0.0014(6) -0.0036(6) 0.0011(6) C9 0.0193(8) 0.0240(8) 0.0186(7) -0.0007(6) -0.0013(6) 0.0019(6) C10 0.0208(8) 0.0205(8) 0.0203(8) 0.0011(6) -0.0022(6) -0.0003(6) C11 0.0224(8) 0.0179(8) 0.0193(7) -0.0008(6) -0.0045(6) 0.0029(6) C12 0.0221(8) 0.0235(8) 0.0217(7) -0.0004(6) 0.0024(6) 0.0019(6) C13 0.0215(8) 0.0201(8) 0.0249(8) 0.0002(6) 0.0006(6) -0.0012(7) C14 0.0222(8) 0.0191(7) 0.0207(7) -0.0010(6) -0.0013(6) -0.0029(6) C15 0.0208(7) 0.0206(8) 0.0242(8) -0.0015(7) -0.0001(6) 0.0007(6) C16 0.0208(8) 0.0254(9) 0.0247(8) 0.0033(7) -0.0037(6) -0.0015(7) C17 0.0265(8) 0.0296(9) 0.0195(7) 0.0002(7) 0.0009(7) -0.0038(7) C18 0.0225(8) 0.0262(8) 0.0238(8) -0.0047(7) 0.0023(7) -0.0013(7) C19 0.0195(7) 0.0233(8) 0.0249(8) -0.0006(6) -0.0024(7) -0.0003(7) C20 0.0214(8) 0.0197(8) 0.0218(7) -0.0005(6) 0.0035(6) 0.0027(7) C21 0.0222(8) 0.0240(8) 0.0245(8) -0.0009(7) 0.0007(7) 0.0010(7) C22 0.0289(9) 0.0206(8) 0.0322(9) -0.0016(7) 0.0065(7) -0.0015(7) C23 0.0338(9) 0.0261(9) 0.0303(9) 0.0085(7) 0.0055(8) 0.0083(8) C24 0.0322(9) 0.0322(9) 0.0239(8) 0.0012(7) -0.0015(7) 0.0052(7) C25 0.0282(8) 0.0229(8) 0.0243(8) -0.0014(6) -0.0018(7) 0.0033(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.09857(17) 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 N1 . C1 . 1.3424(19) yes N1 . C5 . 1.3515(19) yes N2 . C11 . 1.4247(19) yes N2 . C14 . 1.4181(18) yes N2 . C20 . 1.4175(19) yes C1 . C1 2_565 1.491(3) yes C1 . C2 . 1.395(2) yes C2 . C3 . 1.382(2) yes C2 . H21 . 0.962 no C3 . C4 . 1.382(2) yes C3 . H31 . 0.962 no C4 . C5 . 1.394(2) yes C4 . H41 . 0.945 no C5 . C6 . 1.467(2) yes C6 . C7 . 1.337(2) yes C6 . H61 . 0.981 no C7 . C8 . 1.461(2) yes C7 . H71 . 0.950 no C8 . C9 . 1.403(2) yes C8 . C13 . 1.399(2) yes C9 . C10 . 1.383(2) yes C9 . H91 . 0.961 no C10 . C11 . 1.396(2) yes C10 . H101 . 0.975 no C11 . C12 . 1.394(2) yes C12 . C13 . 1.385(2) yes C12 . H121 . 0.971 no C13 . H131 . 0.958 no C14 . C15 . 1.395(2) yes C14 . C19 . 1.394(2) yes C15 . C16 . 1.383(2) yes C15 . H151 . 0.964 no C16 . C17 . 1.385(2) yes C16 . H161 . 0.955 no C17 . C18 . 1.388(2) yes C17 . H171 . 0.960 no C18 . C19 . 1.384(2) yes C18 . H181 . 0.960 no C19 . H191 . 0.956 no C20 . C21 . 1.395(2) yes C20 . C25 . 1.391(2) yes C21 . C22 . 1.385(2) yes C21 . H211 . 0.942 no C22 . C23 . 1.386(2) yes C22 . H221 . 0.960 no C23 . C24 . 1.387(2) yes C23 . H231 . 0.948 no C24 . C25 . 1.383(2) yes C24 . H241 . 0.959 no C25 . H251 . 0.968 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 C1 . N1 . C5 . 118.44(13) yes C11 . N2 . C14 . 119.28(12) yes C11 . N2 . C20 . 119.46(12) yes C14 . N2 . C20 . 120.33(12) yes C1 2_565 C1 . N1 . 116.01(16) yes C1 2_565 C1 . C2 . 121.33(16) yes N1 . C1 . C2 . 122.65(14) yes C1 . C2 . C3 . 118.57(14) yes C1 . C2 . H21 . 119.6 no C3 . C2 . H21 . 121.8 no C2 . C3 . C4 . 119.32(14) yes C2 . C3 . H31 . 121.5 no C4 . C3 . H31 . 119.1 no C3 . C4 . C5 . 119.18(14) yes C3 . C4 . H41 . 119.3 no C5 . C4 . H41 . 121.5 no C4 . C5 . N1 . 121.83(14) yes C4 . C5 . C6 . 120.53(14) yes N1 . C5 . C6 . 117.63(13) yes C5 . C6 . C7 . 123.65(15) yes C5 . C6 . H61 . 117.1 no C7 . C6 . H61 . 119.2 no C6 . C7 . C8 . 127.21(14) yes C6 . C7 . H71 . 118.0 no C8 . C7 . H71 . 114.8 no C7 . C8 . C9 . 123.05(13) yes C7 . C8 . C13 . 119.32(14) yes C9 . C8 . C13 . 117.63(14) yes C8 . C9 . C10 . 121.30(14) yes C8 . C9 . H91 . 118.1 no C10 . C9 . H91 . 120.6 no C9 . C10 . C11 . 120.52(14) yes C9 . C10 . H101 . 121.0 no C11 . C10 . H101 . 118.5 no N2 . C11 . C10 . 120.21(14) yes N2 . C11 . C12 . 121.11(13) yes C10 . C11 . C12 . 118.68(14) yes C11 . C12 . C13 . 120.63(14) yes C11 . C12 . H121 . 120.3 no C13 . C12 . H121 . 119.1 no C8 . C13 . C12 . 121.20(14) yes C8 . C13 . H131 . 119.4 no C12 . C13 . H131 . 119.4 no N2 . C14 . C15 . 120.06(13) yes N2 . C14 . C19 . 120.94(13) yes C15 . C14 . C19 . 118.99(13) yes C14 . C15 . C16 . 120.32(14) yes C14 . C15 . H151 . 119.5 no C16 . C15 . H151 . 120.2 no C15 . C16 . C17 . 120.58(15) yes C15 . C16 . H161 . 119.7 no C17 . C16 . H161 . 119.8 no C16 . C17 . C18 . 119.29(14) yes C16 . C17 . H171 . 120.8 no C18 . C17 . H171 . 119.9 no C17 . C18 . C19 . 120.56(15) yes C17 . C18 . H181 . 119.0 no C19 . C18 . H181 . 120.5 no C14 . C19 . C18 . 120.25(15) yes C14 . C19 . H191 . 119.4 no C18 . C19 . H191 . 120.3 no N2 . C20 . C21 . 120.41(14) yes N2 . C20 . C25 . 120.68(14) yes C21 . C20 . C25 . 118.91(14) yes C20 . C21 . C22 . 120.30(15) yes C20 . C21 . H211 . 118.5 no C22 . C21 . H211 . 121.2 no C21 . C22 . C23 . 120.50(15) yes C21 . C22 . H221 . 120.5 no C23 . C22 . H221 . 119.0 no C22 . C23 . C24 . 119.33(15) yes C22 . C23 . H231 . 121.2 no C24 . C23 . H231 . 119.4 no C23 . C24 . C25 . 120.42(15) yes C23 . C24 . H241 . 119.0 no C25 . C24 . H241 . 120.5 no C20 . C25 . C24 . 120.53(16) yes C20 . C25 . H251 . 118.6 no C24 . C25 . H251 . 120.9 no _iucr_refine_instruction_details_constraints ; # # Punched on 10/12/11 at 12:05:29 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 10/12/11 at 12:05:29 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ;