# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Housecroft, Catherine E' _publ_contact_author_email ? _publ_section_title ; Enantioselective catalysts for the Henry reaction: fine-tuning the catalytic components ; _publ_author_name C.Housecroft # Attachment '- GQ17.cif' data_gq17_123k _database_code_depnum_ccdc_archive 'CCDC 739378' _audit_creation_date 09-05-06 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 'gq17_123k_0ma in C2' _chemical_name_systematic ? _chemical_melting_point ? _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_related_literature # Not in version 2.3.1 ############################################################### # Essential references (e.g. to the origin of the material studied, related # structural studies, and to information supporting the reported structure) # should be cited in this section, with appropriate very brief explanatory # text, for example `The synthesis of the complex is described by Jones # (2001). The anhydrous complex has essentially the same coordination # geometry (Smith, 2003).' In addition, all references included in the # supplementary materials, but not elsewhere in the published article, # should be given here. The simple text `For related literature, see:...' # may be used, but further details should be provided in the Comment # section, which forms part of the supplementary material. ############################################################### ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fig. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; # data_1 _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # End of 'script/refcif-b.dat' #end of refcif _cell_length_a 20.1947(8) _cell_length_b 14.0122(8) _cell_length_c 9.4085(5) _cell_angle_alpha 90 _cell_angle_beta 96.926(4) _cell_angle_gamma 90 _cell_volume 2642.9(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2 ' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z -x,y,-z -x+1/2,y+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' 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 = C30 H30 Cu1 N2 O4 # Dc = 1.37 Fooo = 1204.00 Mu = 8.65 M = 546.13 # Found Formula = C32 H34 Cu1 N2 O4 # Dc = 1.44 FOOO = 1204.00 Mu = 8.68 M = 574.18 _chemical_formula_sum 'C32 H34 Cu1 N2 O4' _chemical_formula_moiety 'C32 H34 Cu1 N2 O4' _chemical_compound_source ? _chemical_formula_weight 574.18 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 123 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1204 _exptl_absorpt_coefficient_mu 0.868 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.96 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type 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 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 76654 _reflns_number_total 12023 _diffrn_reflns_av_R_equivalents 0.041 # Number of reflections with Friedels Law is 6237 # Number of reflections without Friedels Law is 12023 # Theoretical number of reflections is about 6084 _diffrn_reflns_theta_min 2.032 _diffrn_reflns_theta_max 35.666 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 34.953 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -32 _reflns_limit_h_max 32 _reflns_limit_k_min -22 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _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 geom _refine_diff_density_min -1.10 _refine_diff_density_max 1.07 # 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 8030 _refine_ls_number_restraints 1 _refine_ls_number_parameters 354 _oxford_refine_ls_R_factor_ref 0.0240 _refine_ls_wR_factor_ref 0.0265 _refine_ls_goodness_of_fit_ref 1.0690 _refine_ls_shift/su_max 0.000275 # The values computed from all data _oxford_reflns_number_all 12008 _refine_ls_R_factor_all 0.0403 _refine_ls_wR_factor_all 0.0359 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 9119 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_gt 0.0281 _refine_ls_abs_structure_Flack 0.000(5) _refine_ls_abs_structure_details 'Flack (1983), 5786 Friedel-pairs' # 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 ad _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: 0.594 0.213 0.398 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.0000 0.48961(4) 0.5000 0.0117 1.0000 Uani S T . . . . . Cu2 Cu 0.0000 0.53272(4) 0.0000 0.0124 1.0000 Uani S T . . . . . N1 N 0.05490(7) 0.38235(11) 0.43044(14) 0.0138 1.0000 Uani . . . . . . . N2 N -0.04868(7) 0.63899(11) 0.08960(14) 0.0141 1.0000 Uani . . . . . . . O1 O 0.03216(5) 0.58328(8) 0.37660(11) 0.0157 1.0000 Uani . . . . . . . O2 O 0.10615(6) 0.74863(9) 0.35774(12) 0.0182 1.0000 Uani . . . . . . . O3 O -0.05950(5) 0.43549(7) 0.05351(11) 0.0156 1.0000 Uani . . . . . . . O4 O -0.11265(6) 0.27101(9) 0.17046(12) 0.0176 1.0000 Uani . . . . . . . C1 C 0.09290(7) 0.57698(11) 0.33628(14) 0.0128 1.0000 Uani . . . . . . . C2 C 0.13239(8) 0.66016(12) 0.32950(15) 0.0154 1.0000 Uani . . . . . . . C3 C 0.19510(7) 0.65657(11) 0.28438(15) 0.0196 1.0000 Uani . . . . . . . C4 C 0.22166(7) 0.57003(12) 0.24645(16) 0.0224 1.0000 Uani . . . . . . . C5 C 0.18439(8) 0.48767(15) 0.25258(17) 0.0195 1.0000 Uani . . . . . . . C6 C 0.12040(7) 0.49040(12) 0.29462(14) 0.0147 1.0000 Uani . . . . . . . C7 C 0.07970(7) 0.40087(9) 0.29084(13) 0.0159 1.0000 Uani . . . . . . . C8 C 0.01483(7) 0.29280(9) 0.42877(13) 0.0136 1.0000 Uani . . . . . . . C9 C 0.05288(8) 0.20344(12) 0.39757(15) 0.0149 1.0000 Uani . . . . . . . C10 C 0.10106(9) 0.16268(14) 0.49785(17) 0.0225 1.0000 Uani . . . . . . . C11 C 0.13560(10) 0.08207(15) 0.46308(19) 0.0262 1.0000 Uani . . . . . . . C12 C 0.12168(9) 0.04031(14) 0.32804(18) 0.0236 1.0000 Uani . . . . . . . C13 C 0.07351(8) 0.07981(11) 0.22909(16) 0.0200 1.0000 Uani . . . . . . . C14 C 0.03957(8) 0.16146(12) 0.26342(15) 0.0175 1.0000 Uani . . . . . . . C15 C 0.10347(8) 0.76721(12) 0.50749(16) 0.0225 1.0000 Uani . . . . . . . C16 C 0.17060(9) 0.79877(12) 0.58066(18) 0.0263 1.0000 Uani . . . . . . . C21 C -0.10694(7) 0.44415(12) 0.13865(15) 0.0137 1.0000 Uani . . . . . . . C22 C -0.13360(8) 0.36198(12) 0.19957(15) 0.0144 1.0000 Uani . . . . . . . C23 C -0.17950(7) 0.36987(11) 0.29816(14) 0.0175 1.0000 Uani . . . . . . . C24 C -0.20216(7) 0.45850(11) 0.33827(15) 0.0201 1.0000 Uani . . . . . . . C25 C -0.18046(8) 0.53925(14) 0.27301(17) 0.0185 1.0000 Uani . . . . . . . C26 C -0.13490(7) 0.53319(12) 0.17261(15) 0.0148 1.0000 Uani . . . . . . . C27 C -0.12018(7) 0.62035(10) 0.09010(15) 0.0172 1.0000 Uani . . . . . . . C28 C -0.03710(6) 0.72742(9) 0.00804(14) 0.0138 1.0000 Uani . . . . . . . C29 C -0.06242(8) 0.81778(12) 0.07146(16) 0.0150 1.0000 Uani . . . . . . . C30 C -0.11748(8) 0.86458(13) -0.00001(17) 0.0193 1.0000 Uani . . . . . . . C31 C -0.14025(9) 0.94982(14) 0.0539(2) 0.0240 1.0000 Uani . . . . . . . C32 C -0.10795(9) 0.98822(14) 0.17776(19) 0.0237 1.0000 Uani . . . . . . . C33 C -0.05373(8) 0.94133(12) 0.25115(17) 0.0215 1.0000 Uani . . . . . . . C34 C -0.03095(8) 0.85630(11) 0.19820(16) 0.0185 1.0000 Uani . . . . . . . C36 C -0.12174(9) 0.24343(11) 0.02158(15) 0.0213 1.0000 Uani . . . . . . . C37 C -0.19447(10) 0.23589(15) -0.03755(19) 0.0320 1.0000 Uani . . . . . . . H1 H 0.0886 0.3752 0.4914 0.0211 1.0000 Uiso R . . . . . . H2 H -0.0312 0.6452 0.1791 0.0226 1.0000 Uiso R . . . . . . H31 H 0.2191 0.7138 0.2783 0.0254 1.0000 Uiso R . . . . . . H41 H 0.2646 0.5684 0.2176 0.0271 1.0000 Uiso R . . . . . . H51 H 0.2026 0.4277 0.2295 0.0216 1.0000 Uiso R . . . . . . H71 H 0.0407 0.4049 0.2226 0.0205 1.0000 Uiso R . . . . . . H72 H 0.1061 0.3466 0.2667 0.0205 1.0000 Uiso R . . . . . . H81 H -0.0203 0.2962 0.3538 0.0206 1.0000 Uiso R . . . . . . H101 H 0.1126 0.1882 0.5898 0.0269 1.0000 Uiso R . . . . . . H111 H 0.1691 0.0550 0.5312 0.0301 1.0000 Uiso R . . . . . . H121 H 0.1448 -0.0156 0.3068 0.0279 1.0000 Uiso R . . . . . . H131 H 0.0627 0.0512 0.1396 0.0255 1.0000 Uiso R . . . . . . H141 H 0.0063 0.1885 0.1976 0.0211 1.0000 Uiso R . . . . . . H151 H 0.0880 0.7100 0.5530 0.0288 1.0000 Uiso R . . . . . . H152 H 0.0723 0.8200 0.5104 0.0284 1.0000 Uiso R . . . . . . H161 H 0.1705 0.8079 0.6802 0.0390 1.0000 Uiso R . . . . . . H162 H 0.2049 0.7503 0.5715 0.0384 1.0000 Uiso R . . . . . . H163 H 0.1856 0.8569 0.5410 0.0389 1.0000 Uiso R . . . . . . H231 H -0.1953 0.3136 0.3394 0.0212 1.0000 Uiso R . . . . . . H241 H -0.2319 0.4644 0.4040 0.0256 1.0000 Uiso R . . . . . . H251 H -0.1955 0.6014 0.2981 0.0227 1.0000 Uiso R . . . . . . H271 H -0.1399 0.6160 -0.0056 0.0220 1.0000 Uiso R . . . . . . H272 H -0.1401 0.6746 0.1332 0.0219 1.0000 Uiso R . . . . . . H281 H -0.0616 0.7233 -0.0826 0.0213 1.0000 Uiso R . . . . . . H301 H -0.1394 0.8396 -0.0846 0.0240 1.0000 Uiso R . . . . . . H311 H -0.1763 0.9794 0.0055 0.0315 1.0000 Uiso R . . . . . . H321 H -0.1208 1.0464 0.2119 0.0289 1.0000 Uiso R . . . . . . H331 H -0.0326 0.9677 0.3366 0.0269 1.0000 Uiso R . . . . . . H341 H 0.0050 0.8256 0.2480 0.0238 1.0000 Uiso R . . . . . . H361 H -0.1013 0.1806 0.0188 0.0259 1.0000 Uiso R . . . . . . H362 H -0.0998 0.2887 -0.0345 0.0258 1.0000 Uiso R . . . . . . H371 H -0.2000 0.2177 -0.1358 0.0497 1.0000 Uiso R . . . . . . H372 H -0.2159 0.1903 0.0154 0.0502 1.0000 Uiso R . . . . . . H373 H -0.2154 0.2985 -0.0332 0.0494 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 0.01276(11) 0.01138(12) 0.01143(10) 0.0000 0.00371(9) 0.0000 Cu2 0.01421(11) 0.01082(12) 0.01309(10) 0.0000 0.00501(9) 0.0000 N1 0.0169(5) 0.0135(6) 0.0114(4) 0.0004(4) 0.0032(4) -0.0007(4) N2 0.0151(5) 0.0125(5) 0.0156(5) 0.0004(4) 0.0052(4) 0.0000(4) O1 0.0145(4) 0.0150(4) 0.0186(4) 0.0026(3) 0.0067(3) 0.0016(3) O2 0.0226(5) 0.0148(5) 0.0178(5) -0.0007(4) 0.0045(4) 0.0001(4) O3 0.0182(4) 0.0132(4) 0.0170(4) -0.0007(3) 0.0086(3) -0.0017(3) O4 0.0251(5) 0.0152(5) 0.0122(4) 0.0010(3) 0.0009(4) -0.0010(4) C1 0.0122(5) 0.0150(6) 0.0112(5) 0.0010(4) 0.0018(4) -0.0002(4) C2 0.0148(5) 0.0187(6) 0.0129(5) 0.0006(5) 0.0022(4) -0.0013(5) C3 0.0153(5) 0.0240(6) 0.0197(6) -0.0001(5) 0.0030(4) -0.0042(5) C4 0.0145(5) 0.0309(7) 0.0228(6) 0.0017(5) 0.0064(5) 0.0014(5) C5 0.0181(6) 0.0237(7) 0.0176(5) 0.0004(6) 0.0067(4) 0.0049(6) C6 0.0163(5) 0.0160(5) 0.0123(5) 0.0019(5) 0.0041(4) 0.0011(5) C7 0.0213(6) 0.0150(5) 0.0123(5) 0.0000(4) 0.0055(4) 0.0000(4) C8 0.0173(5) 0.0127(5) 0.0107(4) -0.0009(4) 0.0015(4) 0.0003(4) C9 0.0176(6) 0.0125(6) 0.0148(5) -0.0005(4) 0.0035(4) 0.0005(4) C10 0.0302(8) 0.0198(7) 0.0169(6) -0.0048(5) 0.0004(5) 0.0055(6) C11 0.0314(8) 0.0246(8) 0.0207(7) -0.0039(6) -0.0047(6) 0.0105(7) C12 0.0279(7) 0.0202(7) 0.0233(6) -0.0030(5) 0.0054(5) 0.0077(6) C13 0.0262(7) 0.0169(6) 0.0178(6) -0.0049(4) 0.0063(5) -0.0009(5) C14 0.0206(6) 0.0185(6) 0.0135(5) -0.0017(4) 0.0019(4) 0.0001(5) C15 0.0255(7) 0.0236(7) 0.0189(6) -0.0044(5) 0.0051(5) -0.0018(5) C16 0.0311(8) 0.0231(7) 0.0236(7) -0.0019(5) -0.0006(6) -0.0037(6) C21 0.0139(5) 0.0157(6) 0.0114(5) 0.0001(4) 0.0016(4) -0.0011(4) C22 0.0166(6) 0.0141(6) 0.0121(5) 0.0014(4) 0.0007(4) -0.0022(4) C23 0.0164(5) 0.0214(6) 0.0150(5) 0.0026(4) 0.0024(4) -0.0047(4) C24 0.0166(5) 0.0257(6) 0.0190(6) 0.0003(5) 0.0062(4) -0.0031(5) C25 0.0158(6) 0.0205(7) 0.0202(6) -0.0008(5) 0.0064(5) -0.0021(5) C26 0.0136(5) 0.0140(5) 0.0172(5) 0.0007(5) 0.0035(4) -0.0007(5) C27 0.0151(5) 0.0148(5) 0.0223(6) 0.0019(4) 0.0047(4) 0.0020(4) C28 0.0161(5) 0.0119(5) 0.0141(5) 0.0005(4) 0.0048(4) 0.0002(4) C29 0.0166(6) 0.0125(6) 0.0173(6) -0.0001(4) 0.0076(5) -0.0006(4) C30 0.0213(7) 0.0181(6) 0.0188(6) 0.0032(5) 0.0034(5) 0.0020(5) C31 0.0249(7) 0.0180(7) 0.0307(8) 0.0038(6) 0.0095(6) 0.0091(6) C32 0.0280(7) 0.0142(6) 0.0317(7) -0.0033(6) 0.0155(6) 0.0012(6) C33 0.0232(7) 0.0197(6) 0.0230(6) -0.0048(5) 0.0089(5) -0.0021(5) C34 0.0189(6) 0.0173(6) 0.0204(6) -0.0020(5) 0.0059(5) 0.0017(5) C36 0.0314(8) 0.0169(6) 0.0163(6) -0.0021(4) 0.0053(5) -0.0059(5) C37 0.0345(8) 0.0362(9) 0.0233(7) -0.0019(6) -0.0048(6) -0.0084(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.24290(16) 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 3_556 2.0227(15) yes Cu1 . O1 3_556 1.9168(10) yes Cu1 . N1 . 2.0227(15) yes Cu1 . O1 . 1.9168(10) yes Cu2 . N2 3_555 2.0236(14) yes Cu2 . O3 3_555 1.9233(10) yes Cu2 . N2 . 2.0236(14) yes Cu2 . O3 . 1.9233(10) yes N1 . C7 . 1.4839(18) yes N1 . C8 . 1.4921(19) yes N1 . H1 . 0.842 no N2 . C27 . 1.4680(19) yes N2 . C28 . 1.4907(19) yes N2 . H2 . 0.878 no O1 . C1 . 1.3299(16) yes O2 . C2 . 1.387(2) yes O2 . C15 . 1.4402(19) yes O3 . C21 . 1.3264(17) yes O4 . C22 . 1.381(2) yes O4 . C36 . 1.4433(18) yes C1 . C2 . 1.418(2) yes C1 . C6 . 1.409(2) yes C2 . C3 . 1.384(2) yes C3 . C4 . 1.390(2) yes C3 . H31 . 0.942 no C4 . C5 . 1.383(3) yes C4 . H41 . 0.940 no C5 . C6 . 1.397(2) yes C5 . H51 . 0.953 no C6 . C7 . 1.498(2) yes C7 . H71 . 0.956 no C7 . H72 . 0.970 no C8 . C8 3_556 1.533(2) yes C8 . C9 . 1.516(2) yes C8 . H81 . 0.939 no C9 . C10 . 1.393(2) yes C9 . C14 . 1.389(2) yes C10 . C11 . 1.387(3) yes C10 . H101 . 0.939 no C11 . C12 . 1.396(2) yes C11 . H111 . 0.952 no C12 . C13 . 1.379(2) yes C12 . H121 . 0.946 no C13 . C14 . 1.392(2) yes C13 . H131 . 0.935 no C14 . H141 . 0.937 no C15 . C16 . 1.511(2) yes C15 . H151 . 0.978 no C15 . H152 . 0.974 no C16 . H161 . 0.945 no C16 . H162 . 0.981 no C16 . H163 . 0.960 no C21 . C22 . 1.421(2) yes C21 . C26 . 1.422(2) yes C22 . C23 . 1.392(2) yes C23 . C24 . 1.391(2) yes C23 . H231 . 0.951 no C24 . C25 . 1.383(2) yes C24 . H241 . 0.917 no C25 . C26 . 1.398(2) yes C25 . H251 . 0.961 no C26 . C27 . 1.496(2) yes C27 . H271 . 0.941 no C27 . H272 . 0.971 no C28 . C28 3_555 1.524(3) yes C28 . C29 . 1.515(2) yes C28 . H281 . 0.935 no C29 . C30 . 1.392(2) yes C29 . C34 . 1.391(2) yes C30 . C31 . 1.397(3) yes C30 . H301 . 0.931 no C31 . C32 . 1.375(3) yes C31 . H311 . 0.911 no C32 . C33 . 1.387(3) yes C32 . H321 . 0.925 no C33 . C34 . 1.391(2) yes C33 . H331 . 0.939 no C34 . H341 . 0.921 no C36 . C37 . 1.510(3) yes C36 . H361 . 0.975 no C36 . H362 . 0.967 no C37 . H371 . 0.952 no C37 . H372 . 0.946 no C37 . H373 . 0.978 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 N1 3_556 Cu1 . O1 3_556 94.24(5) yes N1 3_556 Cu1 . N1 . 84.01(8) yes O1 3_556 Cu1 . N1 . 160.69(5) yes N1 3_556 Cu1 . O1 . 160.69(5) yes O1 3_556 Cu1 . O1 . 93.57(6) yes N1 . Cu1 . O1 . 94.24(5) yes N2 3_555 Cu2 . O3 3_555 93.55(5) yes N2 3_555 Cu2 . N2 . 85.23(8) yes O3 3_555 Cu2 . N2 . 168.69(5) yes N2 3_555 Cu2 . O3 . 168.69(5) yes O3 3_555 Cu2 . O3 . 89.80(6) yes N2 . Cu2 . O3 . 93.55(5) yes Cu1 . N1 . C7 . 114.40(9) yes Cu1 . N1 . C8 . 108.10(9) yes C7 . N1 . C8 . 112.22(11) yes Cu1 . N1 . H1 . 107.4 no C7 . N1 . H1 . 107.0 no C8 . N1 . H1 . 107.4 no Cu2 . N2 . C27 . 113.44(10) yes Cu2 . N2 . C28 . 106.44(9) yes C27 . N2 . C28 . 111.41(11) yes Cu2 . N2 . H2 . 108.3 no C27 . N2 . H2 . 107.3 no C28 . N2 . H2 . 110.0 no Cu1 . O1 . C1 . 121.26(9) yes C2 . O2 . C15 . 114.17(12) yes Cu2 . O3 . C21 . 127.79(9) yes C22 . O4 . C36 . 115.69(12) yes O1 . C1 . C2 . 120.09(14) yes O1 . C1 . C6 . 122.98(13) yes C2 . C1 . C6 . 116.90(13) yes C1 . C2 . O2 . 119.76(14) yes C1 . C2 . C3 . 121.62(15) yes O2 . C2 . C3 . 118.44(14) yes C2 . C3 . C4 . 120.41(14) yes C2 . C3 . H31 . 118.9 no C4 . C3 . H31 . 120.6 no C3 . C4 . C5 . 119.24(13) yes C3 . C4 . H41 . 119.5 no C5 . C4 . H41 . 121.2 no C4 . C5 . C6 . 121.06(16) yes C4 . C5 . H51 . 120.0 no C6 . C5 . H51 . 118.9 no C1 . C6 . C5 . 120.74(15) yes C1 . C6 . C7 . 119.61(12) yes C5 . C6 . C7 . 119.61(15) yes C6 . C7 . N1 . 111.61(11) yes C6 . C7 . H71 . 111.8 no N1 . C7 . H71 . 105.4 no C6 . C7 . H72 . 110.3 no N1 . C7 . H72 . 108.9 no H71 . C7 . H72 . 108.7 no C8 3_556 C8 . N1 . 105.04(9) yes C8 3_556 C8 . C9 . 115.47(9) yes N1 . C8 . C9 . 114.19(12) yes C8 3_556 C8 . H81 . 108.5 no N1 . C8 . H81 . 108.9 no C9 . C8 . H81 . 104.5 no C8 . C9 . C10 . 122.42(13) yes C8 . C9 . C14 . 118.59(13) yes C10 . C9 . C14 . 118.98(15) yes C9 . C10 . C11 . 120.26(15) yes C9 . C10 . H101 . 122.9 no C11 . C10 . H101 . 116.8 no C10 . C11 . C12 . 120.27(16) yes C10 . C11 . H111 . 120.1 no C12 . C11 . H111 . 119.6 no C11 . C12 . C13 . 119.63(16) yes C11 . C12 . H121 . 119.3 no C13 . C12 . H121 . 121.0 no C12 . C13 . C14 . 120.03(14) yes C12 . C13 . H131 . 120.4 no C14 . C13 . H131 . 119.6 no C13 . C14 . C9 . 120.82(14) yes C13 . C14 . H141 . 120.9 no C9 . C14 . H141 . 118.3 no O2 . C15 . C16 . 111.18(13) yes O2 . C15 . H151 . 109.4 no C16 . C15 . H151 . 110.9 no O2 . C15 . H152 . 105.4 no C16 . C15 . H152 . 108.2 no H151 . C15 . H152 . 111.7 no C15 . C16 . H161 . 112.5 no C15 . C16 . H162 . 111.2 no H161 . C16 . H162 . 105.4 no C15 . C16 . H163 . 112.3 no H161 . C16 . H163 . 108.0 no H162 . C16 . H163 . 107.1 no O3 . C21 . C22 . 120.40(14) yes O3 . C21 . C26 . 123.47(13) yes C22 . C21 . C26 . 116.13(13) yes C21 . C22 . O4 . 121.87(14) yes C21 . C22 . C23 . 121.30(15) yes O4 . C22 . C23 . 116.73(13) yes C22 . C23 . C24 . 121.24(13) yes C22 . C23 . H231 . 119.3 no C24 . C23 . H231 . 119.4 no C23 . C24 . C25 . 118.52(13) yes C23 . C24 . H241 . 121.8 no C25 . C24 . H241 . 119.6 no C24 . C25 . C26 . 121.30(16) yes C24 . C25 . H251 . 120.3 no C26 . C25 . H251 . 118.3 no C21 . C26 . C25 . 121.11(15) yes C21 . C26 . C27 . 119.38(12) yes C25 . C26 . C27 . 119.28(14) yes C26 . C27 . N2 . 113.83(11) yes C26 . C27 . H271 . 110.9 no N2 . C27 . H271 . 108.1 no C26 . C27 . H272 . 107.7 no N2 . C27 . H272 . 108.6 no H271 . C27 . H272 . 107.6 no C28 3_555 C28 . N2 . 105.57(9) yes C28 3_555 C28 . C29 . 114.95(9) yes N2 . C28 . C29 . 114.25(11) yes C28 3_555 C28 . H281 . 109.1 no N2 . C28 . H281 . 108.7 no C29 . C28 . H281 . 104.2 no C28 . C29 . C30 . 119.43(14) yes C28 . C29 . C34 . 121.40(14) yes C30 . C29 . C34 . 119.15(15) yes C29 . C30 . C31 . 120.40(16) yes C29 . C30 . H301 . 120.3 no C31 . C30 . H301 . 119.3 no C30 . C31 . C32 . 119.94(17) yes C30 . C31 . H311 . 119.1 no C32 . C31 . H311 . 120.9 no C31 . C32 . C33 . 120.12(17) yes C31 . C32 . H321 . 121.0 no C33 . C32 . H321 . 118.8 no C32 . C33 . C34 . 120.18(16) yes C32 . C33 . H331 . 119.3 no C34 . C33 . H331 . 120.5 no C33 . C34 . C29 . 120.18(15) yes C33 . C34 . H341 . 119.5 no C29 . C34 . H341 . 120.3 no O4 . C36 . C37 . 112.36(14) yes O4 . C36 . H361 . 105.3 no C37 . C36 . H361 . 108.9 no O4 . C36 . H362 . 109.9 no C37 . C36 . H362 . 109.5 no H361 . C36 . H362 . 110.8 no C36 . C37 . H371 . 111.8 no C36 . C37 . H372 . 109.8 no H371 . C37 . H372 . 108.9 no C36 . C37 . H373 . 109.2 no H371 . C37 . H373 . 106.2 no H372 . C37 . H373 . 110.9 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 . H1 . C23 3_556 171 0.84 2.53 3.366(2) yes N2 . H2 . O1 . 149 0.88 2.30 3.083(2) yes C7 . H71 . O3 . 173 0.96 2.46 3.407(2) yes C8 . H81 . O4 . 168 0.94 2.41 3.335(2) yes C10 . H101 . O4 3_556 165 0.94 2.54 3.453(2) yes C34 . H341 . O2 . 174 0.92 2.43 3.345(2) yes C36 . H362 . O3 . 123 0.97 2.33 2.970(2) yes # Attachment '- GQ70.CIF' data_gq70 _database_code_depnum_ccdc_archive 'CCDC 739379' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H35.34 Cu0.33 N2 O4, C32 H34 Cu N2 O4' _chemical_formula_sum 'C64 H69.34 Cu1.33 N4 O8' _chemical_formula_weight 1107.10 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall C2y 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' _cell_length_a 20.412(4) _cell_length_b 13.926(3) _cell_length_c 9.4341(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.94(3) _cell_angle_gamma 90.00 _cell_volume 2656.0(10) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.605 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8394 _exptl_absorpt_correction_T_max 0.9762 _exptl_absorpt_process_details '(Blessing 1951)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53792 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 31.50 _reflns_number_total 8697 _reflns_number_gt 8662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS' _computing_cell_refinement 'Stoe IPDS' _computing_data_reduction 'Stoe IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+1.8196P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.057(8) _refine_ls_number_reflns 8697 _refine_ls_number_parameters 371 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.126 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1B O 1.07028(9) 0.92733(10) 0.94681(16) 0.0292(3) Uani 1 1 d D . . H1BB H 1.070(2) 0.9866(16) 0.971(5) 0.035 Uiso 0.67 1 d PD A 1 O2B O 1.11859(9) 0.76101(11) 0.82955(15) 0.0308(3) Uani 1 1 d . . . N1B N 1.05145(8) 1.11985(11) 0.90671(17) 0.0209(3) Uani 1 1 d D . . H1C H 1.0299(14) 1.129(2) 0.821(2) 0.025 Uiso 1 1 d D . . C1B C 1.03708(9) 1.20390(14) 0.99298(18) 0.0216(3) Uani 1 1 d D . . H1A H 1.0591(14) 1.189(2) 1.093(2) 0.026 Uiso 1 1 d D . . C2B C 1.06062(9) 1.29767(12) 0.9350(2) 0.0218(3) Uani 1 1 d . . . C3B C 1.03074(10) 1.33570(15) 0.8062(2) 0.0272(3) Uani 1 1 d . . . H3AA H 0.9946 1.3031 0.7529 0.033 Uiso 1 1 calc R . . C4B C 1.05336(11) 1.42112(16) 0.7547(3) 0.0322(4) Uani 1 1 d . . . H4AA H 1.0326 1.4466 0.6664 0.039 Uiso 1 1 calc R . . C5B C 1.10616(11) 1.46959(16) 0.8317(3) 0.0346(4) Uani 1 1 d . . . H5AA H 1.1209 1.5287 0.7971 0.042 Uiso 1 1 calc R . . C6B C 1.13703(12) 1.43173(16) 0.9581(3) 0.0347(4) Uani 1 1 d . . . H6AA H 1.1739 1.4638 1.0097 0.042 Uiso 1 1 calc R . . C7B C 1.11418(10) 1.34638(15) 1.0105(2) 0.0283(3) Uani 1 1 d . . . H7AA H 1.1353 1.3210 1.0986 0.034 Uiso 1 1 calc R . . C8B C 1.12216(9) 1.11348(14) 0.8941(2) 0.0278(3) Uani 1 1 d . . . H8AA H 1.1478 1.1149 0.9912 0.033 Uiso 1 1 calc R . . H8AB H 1.1350 1.1704 0.8415 0.033 Uiso 1 1 calc R . . C9B C 1.14003(9) 1.02446(14) 0.8185(2) 0.0244(3) Uani 1 1 d . . . C10B C 1.11585(11) 0.93502(13) 0.8559(2) 0.0251(3) Uani 1 1 d . . . C11B C 1.14018(11) 0.85144(13) 0.79770(19) 0.0257(3) Uani 1 1 d . . . C12B C 1.18393(11) 0.85846(15) 0.6991(2) 0.0293(4) Uani 1 1 d . . . H12A H 1.2000 0.8016 0.6601 0.035 Uiso 1 1 calc R . . C13B C 1.20490(11) 0.94764(17) 0.6558(2) 0.0317(4) Uani 1 1 d . . . H13A H 1.2336 0.9520 0.5848 0.038 Uiso 1 1 calc R . . C14B C 1.18328(10) 1.03009(16) 0.7177(2) 0.0300(4) Uani 1 1 d . . . H14A H 1.1983 1.0911 0.6908 0.036 Uiso 1 1 calc R . . C15B C 1.12935(14) 0.73293(15) 0.9781(2) 0.0351(4) Uani 1 1 d . . . H15A H 1.1068 0.6710 0.9890 0.042 Uiso 1 1 calc R . . H15B H 1.1093 0.7816 1.0355 0.042 Uiso 1 1 calc R . . C16B C 1.20152(18) 0.7227(2) 1.0351(3) 0.0523(7) Uani 1 1 d . . . H16A H 1.2225 0.6791 0.9734 0.078 Uiso 1 1 calc R . . H16B H 1.2061 0.6966 1.1324 0.078 Uiso 1 1 calc R . . H16C H 1.2229 0.7857 1.0366 0.078 Uiso 1 1 calc R . . O1A O 0.96449(7) 1.07366(10) 0.61730(16) 0.0244(3) Uani 1 1 d . . . O2A O 0.88958(8) 1.23703(10) 0.64059(17) 0.0288(3) Uani 1 1 d . . . N1A N 0.94652(8) 0.87229(11) 0.57160(15) 0.0186(2) Uani 1 1 d D . . H1B H 0.9106(11) 0.864(2) 0.501(3) 0.022 Uiso 1 1 d D . . H1 H 1.0254(11) 0.786(2) 0.645(3) 0.022 Uiso 1 1 d D . . C1A C 0.98643(9) 0.78272(12) 0.57159(17) 0.0197(3) Uani 1 1 d D . . C2A C 0.94936(9) 0.69297(13) 0.60290(18) 0.0217(3) Uani 1 1 d . . . C3A C 0.96300(10) 0.65123(14) 0.7371(2) 0.0262(3) Uani 1 1 d . . . H3BA H 0.9958 0.6788 0.8064 0.031 Uiso 1 1 calc R . . C4A C 0.92926(11) 0.56941(15) 0.7718(2) 0.0299(4) Uani 1 1 d . . . H4BA H 0.9392 0.5415 0.8642 0.036 Uiso 1 1 calc R . . C5A C 0.88140(12) 0.52895(16) 0.6717(3) 0.0346(4) Uani 1 1 d . . . H5BA H 0.8581 0.4732 0.6947 0.041 Uiso 1 1 calc R . . C6A C 0.86774(14) 0.57035(18) 0.5381(3) 0.0395(5) Uani 1 1 d . . . H6BA H 0.8348 0.5427 0.4690 0.047 Uiso 1 1 calc R . . C7A C 0.90138(12) 0.65194(16) 0.5026(2) 0.0310(4) Uani 1 1 d . . . H7BA H 0.8915 0.6795 0.4100 0.037 Uiso 1 1 calc R . . C8A C 0.92341(11) 0.89069(14) 0.7105(2) 0.0274(4) Uani 1 1 d . . . H8BA H 0.9621 0.8999 0.7850 0.033 Uiso 1 1 calc R . . H8BB H 0.8984 0.8343 0.7376 0.033 Uiso 1 1 calc R . . C9A C 0.88040(8) 0.97744(16) 0.70420(17) 0.0229(3) Uani 1 1 d . . . C10A C 0.90521(9) 1.06526(13) 0.65974(19) 0.0211(3) Uani 1 1 d . . . C11A C 0.86509(9) 1.14728(13) 0.66699(19) 0.0231(3) Uani 1 1 d . . . C12A C 0.80386(10) 1.14128(17) 0.7126(2) 0.0301(4) Uani 1 1 d . . . H12B H 0.7781 1.1977 0.7170 0.036 Uiso 1 1 calc R . . C13A C 0.77939(10) 1.05333(18) 0.7524(2) 0.0325(4) Uani 1 1 d . . . H13B H 0.7369 1.0491 0.7821 0.039 Uiso 1 1 calc R . . C14A C 0.81826(9) 0.97213(18) 0.74776(19) 0.0283(3) Uani 1 1 d . . . H14B H 0.8021 0.9118 0.7748 0.034 Uiso 1 1 calc R . . C15A C 0.89207(11) 1.25714(16) 0.4921(2) 0.0319(4) Uani 1 1 d . . . H15C H 0.9051 1.1983 0.4442 0.038 Uiso 1 1 calc R . . H15D H 0.9260 1.3069 0.4839 0.038 Uiso 1 1 calc R . . C16A C 0.82597(13) 1.29163(17) 0.4177(3) 0.0374(5) Uani 1 1 d . . . H16D H 0.7917 1.2448 0.4321 0.056 Uiso 1 1 calc R . . H16E H 0.8280 1.2988 0.3151 0.056 Uiso 1 1 calc R . . H16F H 0.8153 1.3537 0.4577 0.056 Uiso 1 1 calc R . . Cu1 Cu 1.0000 0.979753(18) 0.5000 0.02174(8) Uani 1 2 d S . . Cu2 Cu 1.0000 1.02015(7) 1.0000 0.02511(18) Uani 0.33 2 d SP . 2 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 O1B 0.0440(8) 0.0204(6) 0.0249(6) -0.0008(5) 0.0105(6) 0.0061(5) O2B 0.0509(9) 0.0189(6) 0.0208(6) -0.0024(5) -0.0015(6) 0.0051(6) N1B 0.0204(6) 0.0193(6) 0.0234(6) 0.0005(5) 0.0043(5) -0.0008(5) C1B 0.0199(6) 0.0266(7) 0.0191(6) -0.0009(6) 0.0051(5) -0.0005(5) C2B 0.0221(7) 0.0206(7) 0.0242(7) -0.0021(6) 0.0087(6) -0.0001(5) C3B 0.0247(7) 0.0290(8) 0.0287(8) 0.0033(7) 0.0066(6) -0.0003(6) C4B 0.0333(9) 0.0290(9) 0.0368(10) 0.0068(7) 0.0134(8) 0.0023(7) C5B 0.0377(9) 0.0220(9) 0.0479(11) -0.0014(8) 0.0193(8) -0.0034(8) C6B 0.0369(10) 0.0261(9) 0.0431(11) -0.0088(8) 0.0125(9) -0.0097(8) C7B 0.0293(8) 0.0254(8) 0.0306(8) -0.0056(7) 0.0053(7) -0.0042(6) C8B 0.0208(7) 0.0207(7) 0.0414(10) -0.0068(7) 0.0028(7) 0.0002(6) C9B 0.0235(7) 0.0218(7) 0.0268(8) -0.0019(6) -0.0010(6) 0.0043(6) C10B 0.0344(9) 0.0200(7) 0.0191(7) -0.0031(6) -0.0025(6) 0.0063(6) C11B 0.0366(9) 0.0204(7) 0.0183(7) -0.0037(6) -0.0021(6) 0.0069(6) C12B 0.0309(9) 0.0298(9) 0.0261(8) -0.0036(7) -0.0001(7) 0.0114(7) C13B 0.0285(8) 0.0338(9) 0.0330(9) -0.0016(7) 0.0052(7) 0.0079(7) C14B 0.0256(8) 0.0279(9) 0.0362(10) 0.0001(7) 0.0030(7) 0.0049(7) C15B 0.0571(13) 0.0251(8) 0.0224(8) 0.0020(6) 0.0032(8) 0.0105(8) C16B 0.0653(18) 0.0522(15) 0.0344(12) 0.0032(11) -0.0106(12) 0.0185(14) O1A 0.0217(6) 0.0220(6) 0.0305(7) -0.0072(5) 0.0071(5) 0.0000(4) O2A 0.0363(7) 0.0214(6) 0.0291(7) -0.0015(5) 0.0057(5) 0.0012(5) N1A 0.0218(6) 0.0188(6) 0.0158(5) 0.0002(5) 0.0042(5) -0.0005(5) C1A 0.0240(7) 0.0195(6) 0.0163(6) 0.0008(5) 0.0050(5) -0.0007(5) C2A 0.0259(7) 0.0189(6) 0.0207(7) 0.0016(5) 0.0049(6) 0.0012(5) C3A 0.0307(8) 0.0252(8) 0.0230(7) 0.0065(6) 0.0049(6) 0.0013(6) C4A 0.0362(9) 0.0268(8) 0.0277(8) 0.0107(7) 0.0080(7) 0.0001(7) C5A 0.0410(11) 0.0271(9) 0.0365(10) 0.0086(8) 0.0089(8) -0.0064(8) C6A 0.0477(13) 0.0332(10) 0.0358(11) 0.0059(9) -0.0006(9) -0.0152(9) C7A 0.0389(10) 0.0293(9) 0.0234(8) 0.0054(7) -0.0003(7) -0.0094(8) C8A 0.0392(10) 0.0252(8) 0.0196(7) 0.0030(6) 0.0111(6) 0.0068(7) C9A 0.0261(7) 0.0241(6) 0.0192(6) -0.0007(7) 0.0053(5) 0.0013(7) C10A 0.0210(7) 0.0212(7) 0.0204(7) -0.0026(5) 0.0002(5) 0.0012(5) C11A 0.0247(7) 0.0215(7) 0.0225(7) -0.0016(6) 0.0019(6) 0.0039(6) C12A 0.0243(8) 0.0360(10) 0.0298(8) -0.0003(7) 0.0023(6) 0.0072(7) C13A 0.0218(8) 0.0431(11) 0.0336(10) -0.0023(8) 0.0073(7) 0.0010(7) C14A 0.0312(8) 0.0321(9) 0.0230(7) -0.0014(7) 0.0086(6) -0.0048(8) C15A 0.0368(10) 0.0282(9) 0.0315(9) 0.0036(7) 0.0074(7) 0.0029(7) C16A 0.0447(12) 0.0294(10) 0.0370(11) 0.0026(8) 0.0017(9) 0.0070(8) Cu1 0.02181(13) 0.02062(13) 0.02334(13) 0.000 0.00516(9) 0.000 Cu2 0.0261(4) 0.0236(4) 0.0268(4) 0.000 0.0077(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1B C10B 1.354(3) . ? O1B Cu2 2.0443(17) . ? O1B H1BB 0.855(19) . ? O2B C11B 1.381(3) . ? O2B C15B 1.442(3) . ? N1B C8B 1.467(2) . ? N1B C1B 1.478(2) . ? N1B Cu2 2.0151(17) . ? N1B H1C 0.876(17) . ? C1B C2B 1.519(3) . ? C1B C1B 1.538(3) 2_757 ? C1B H1A 1.011(17) . ? C2B C3B 1.387(3) . ? C2B C7B 1.396(3) . ? C3B C4B 1.388(3) . ? C3B H3AA 0.9500 . ? C4B C5B 1.388(3) . ? C4B H4AA 0.9500 . ? C5B C6B 1.375(4) . ? C5B H5AA 0.9500 . ? C6B C7B 1.392(3) . ? C6B H6AA 0.9500 . ? C7B H7AA 0.9500 . ? C8B C9B 1.500(3) . ? C8B H8AA 0.9900 . ? C8B H8AB 0.9900 . ? C9B C14B 1.386(3) . ? C9B C10B 1.403(3) . ? C10B C11B 1.407(3) . ? C11B C12B 1.379(3) . ? C12B C13B 1.393(3) . ? C12B H12A 0.9500 . ? C13B C14B 1.388(3) . ? C13B H13A 0.9500 . ? C14B H14A 0.9500 . ? C15B C16B 1.504(4) . ? C15B H15A 0.9900 . ? C15B H15B 0.9900 . ? C16B H16A 0.9800 . ? C16B H16B 0.9800 . ? C16B H16C 0.9800 . ? O1A C10A 1.331(2) . ? O1A Cu1 1.9187(14) . ? O2A C11A 1.381(2) . ? O2A C15A 1.437(3) . ? N1A C8A 1.475(2) . ? N1A C1A 1.490(2) . ? N1A Cu1 2.0227(15) . ? N1A H1B 0.928(17) . ? C1A C2A 1.511(2) . ? C1A C1A 1.529(3) 2_756 ? C1A H1 0.980(17) . ? C2A C3A 1.386(2) . ? C2A C7A 1.387(3) . ? C3A C4A 1.394(3) . ? C3A H3BA 0.9500 . ? C4A C5A 1.382(3) . ? C4A H4BA 0.9500 . ? C5A C6A 1.379(3) . ? C5A H5BA 0.9500 . ? C6A C7A 1.392(3) . ? C6A H6BA 0.9500 . ? C7A H7BA 0.9500 . ? C8A C9A 1.490(3) . ? C8A H8BA 0.9900 . ? C8A H8BB 0.9900 . ? C9A C14A 1.388(2) . ? C9A C10A 1.410(3) . ? C10A C11A 1.413(2) . ? C11A C12A 1.379(3) . ? C12A C13A 1.394(3) . ? C12A H12B 0.9500 . ? C13A C14A 1.385(3) . ? C13A H13B 0.9500 . ? C14A H14B 0.9500 . ? C15A C16A 1.510(3) . ? C15A H15C 0.9900 . ? C15A H15D 0.9900 . ? C16A H16D 0.9800 . ? C16A H16E 0.9800 . ? C16A H16F 0.9800 . ? Cu1 O1A 1.9187(14) 2_756 ? Cu1 N1A 2.0227(15) 2_756 ? Cu2 N1B 2.0151(17) 2_757 ? Cu2 O1B 2.0443(17) 2_757 ? Cu2 H1BB 1.57(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10B O1B Cu2 132.25(12) . . ? C10B O1B H1BB 97(3) . . ? Cu2 O1B H1BB 45(3) . . ? C11B O2B C15B 116.64(16) . . ? C8B N1B C1B 111.39(14) . . ? C8B N1B Cu2 124.85(13) . . ? C1B N1B Cu2 98.63(11) . . ? C8B N1B H1C 108(2) . . ? C1B N1B H1C 106(2) . . ? Cu2 N1B H1C 106(2) . . ? N1B C1B C2B 112.68(14) . . ? N1B C1B C1B 108.66(12) . 2_757 ? C2B C1B C1B 113.27(11) . 2_757 ? N1B C1B H1A 104.7(18) . . ? C2B C1B H1A 113.1(17) . . ? C1B C1B H1A 103.6(17) 2_757 . ? C3B C2B C7B 118.71(18) . . ? C3B C2B C1B 121.40(17) . . ? C7B C2B C1B 119.88(17) . . ? C2B C3B C4B 120.4(2) . . ? C2B C3B H3AA 119.8 . . ? C4B C3B H3AA 119.8 . . ? C3B C4B C5B 120.4(2) . . ? C3B C4B H4AA 119.8 . . ? C5B C4B H4AA 119.8 . . ? C6B C5B C4B 119.8(2) . . ? C6B C5B H5AA 120.1 . . ? C4B C5B H5AA 120.1 . . ? C5B C6B C7B 120.0(2) . . ? C5B C6B H6AA 120.0 . . ? C7B C6B H6AA 120.0 . . ? C6B C7B C2B 120.7(2) . . ? C6B C7B H7AA 119.6 . . ? C2B C7B H7AA 119.6 . . ? N1B C8B C9B 113.26(15) . . ? N1B C8B H8AA 108.9 . . ? C9B C8B H8AA 108.9 . . ? N1B C8B H8AB 108.9 . . ? C9B C8B H8AB 108.9 . . ? H8AA C8B H8AB 107.7 . . ? C14B C9B C10B 120.16(17) . . ? C14B C9B C8B 119.95(18) . . ? C10B C9B C8B 119.79(17) . . ? O1B C10B C9B 121.75(16) . . ? O1B C10B C11B 119.50(18) . . ? C9B C10B C11B 118.75(19) . . ? C12B C11B O2B 117.86(17) . . ? C12B C11B C10B 120.1(2) . . ? O2B C11B C10B 121.95(19) . . ? C11B C12B C13B 120.99(18) . . ? C11B C12B H12A 119.5 . . ? C13B C12B H12A 119.5 . . ? C14B C13B C12B 119.0(2) . . ? C14B C13B H13A 120.5 . . ? C12B C13B H13A 120.5 . . ? C9B C14B C13B 120.8(2) . . ? C9B C14B H14A 119.6 . . ? C13B C14B H14A 119.6 . . ? O2B C15B C16B 112.5(2) . . ? O2B C15B H15A 109.1 . . ? C16B C15B H15A 109.1 . . ? O2B C15B H15B 109.1 . . ? C16B C15B H15B 109.1 . . ? H15A C15B H15B 107.8 . . ? C15B C16B H16A 109.5 . . ? C15B C16B H16B 109.5 . . ? H16A C16B H16B 109.5 . . ? C15B C16B H16C 109.5 . . ? H16A C16B H16C 109.5 . . ? H16B C16B H16C 109.5 . . ? C10A O1A Cu1 123.03(12) . . ? C11A O2A C15A 114.49(16) . . ? C8A N1A C1A 112.79(13) . . ? C8A N1A Cu1 114.94(12) . . ? C1A N1A Cu1 107.40(11) . . ? C8A N1A H1B 110.2(19) . . ? C1A N1A H1B 105.6(19) . . ? Cu1 N1A H1B 105.3(18) . . ? N1A C1A C2A 113.82(14) . . ? N1A C1A C1A 105.36(11) . 2_756 ? C2A C1A C1A 115.15(11) . 2_756 ? N1A C1A H1 110.5(17) . . ? C2A C1A H1 106.4(17) . . ? C1A C1A H1 105.3(17) 2_756 . ? C3A C2A C7A 118.95(17) . . ? C3A C2A C1A 118.85(16) . . ? C7A C2A C1A 122.19(16) . . ? C2A C3A C4A 120.94(19) . . ? C2A C3A H3BA 119.5 . . ? C4A C3A H3BA 119.5 . . ? C5A C4A C3A 119.90(18) . . ? C5A C4A H4BA 120.1 . . ? C3A C4A H4BA 120.1 . . ? C6A C5A C4A 119.3(2) . . ? C6A C5A H5BA 120.4 . . ? C4A C5A H5BA 120.4 . . ? C5A C6A C7A 121.1(2) . . ? C5A C6A H6BA 119.4 . . ? C7A C6A H6BA 119.4 . . ? C2A C7A C6A 119.84(19) . . ? C2A C7A H7BA 120.1 . . ? C6A C7A H7BA 120.1 . . ? N1A C8A C9A 111.37(15) . . ? N1A C8A H8BA 109.4 . . ? C9A C8A H8BA 109.4 . . ? N1A C8A H8BB 109.4 . . ? C9A C8A H8BB 109.4 . . ? H8BA C8A H8BB 108.0 . . ? C14A C9A C10A 120.98(19) . . ? C14A C9A C8A 120.2(2) . . ? C10A C9A C8A 118.78(15) . . ? O1A C10A C9A 123.00(16) . . ? O1A C10A C11A 120.05(17) . . ? C9A C10A C11A 116.91(17) . . ? C12A C11A O2A 118.50(17) . . ? C12A C11A C10A 121.49(18) . . ? O2A C11A C10A 119.74(17) . . ? C11A C12A C13A 120.75(19) . . ? C11A C12A H12B 119.6 . . ? C13A C12A H12B 119.6 . . ? C14A C13A C12A 118.72(19) . . ? C14A C13A H13B 120.6 . . ? C12A C13A H13B 120.6 . . ? C13A C14A C9A 121.1(2) . . ? C13A C14A H14B 119.4 . . ? C9A C14A H14B 119.4 . . ? O2A C15A C16A 111.42(19) . . ? O2A C15A H15C 109.3 . . ? C16A C15A H15C 109.3 . . ? O2A C15A H15D 109.3 . . ? C16A C15A H15D 109.3 . . ? H15C C15A H15D 108.0 . . ? C15A C16A H16D 109.5 . . ? C15A C16A H16E 109.5 . . ? H16D C16A H16E 109.5 . . ? C15A C16A H16F 109.5 . . ? H16D C16A H16F 109.5 . . ? H16E C16A H16F 109.5 . . ? O1A Cu1 O1A 94.07(9) . 2_756 ? O1A Cu1 N1A 92.72(6) . . ? O1A Cu1 N1A 163.97(6) 2_756 . ? O1A Cu1 N1A 163.97(6) . 2_756 ? O1A Cu1 N1A 92.72(6) 2_756 2_756 ? N1A Cu1 N1A 84.56(9) . 2_756 ? N1B Cu2 N1B 92.89(10) 2_757 . ? N1B Cu2 O1B 84.42(7) 2_757 2_757 ? N1B Cu2 O1B 165.60(7) . 2_757 ? N1B Cu2 O1B 165.60(7) 2_757 . ? N1B Cu2 O1B 84.42(7) . . ? O1B Cu2 O1B 101.56(10) 2_757 . ? N1B Cu2 H1BB 145.8(11) 2_757 . ? N1B Cu2 H1BB 65.4(13) . . ? O1B Cu2 H1BB 122.9(11) 2_757 . ? O1B Cu2 H1BB 22.8(9) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.371 _refine_diff_density_min -0.917 _refine_diff_density_rms 0.075 # Attachment '- GQ71.cif' data_gq71_2_123k _database_code_depnum_ccdc_archive 'CCDC 739380' _audit_creation_date 09-05-28 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 'gq71_2_123k_0m in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.4552(2) _cell_length_b 17.3368(4) _cell_length_c 10.8328(2) _cell_angle_alpha 90 _cell_angle_beta 95.4620(10) _cell_angle_gamma 90 _cell_volume 1580.73(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall '-P 2yn' 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 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' 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' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C8 H20 Cu2 I3 N1 # Dc = 2.68 Fooo = 1168.00 Mu = 85.21 M = 638.06 # Found Formula = C8 H20 Cu2 I3 N1 # Dc = 2.68 FOOO = 1168.00 Mu = 85.21 M = 638.06 _chemical_formula_sum 'C8 H20 Cu2 I3 N1' _chemical_formula_moiety 'C8 H20 N, Cu2 I3' _chemical_compound_source ? _chemical_formula_weight 638.06 _cell_measurement_reflns_used 9457 _cell_measurement_theta_min 3 _cell_measurement_theta_max 36 _cell_measurement_temperature 123 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_max 0.42 _exptl_crystal_density_diffrn 2.681 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 8.521 # Sheldrick geometric approximatio 0.20 0.84 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Apex2 (Bruker AXS, 2006)' _exptl_absorpt_correction_T_min 0.18 _exptl_absorpt_correction_T_max 0.84 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type 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 69573 _reflns_number_total 7681 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections with Friedels Law is 7681 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7700 _diffrn_reflns_theta_min 2.224 _diffrn_reflns_theta_max 36.386 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 36.386 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -14 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 28 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 1.18 _oxford_diffrn_Wilson_scale 314.76 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.55 _refine_diff_density_max 1.50 # 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 5956 _refine_ls_number_restraints 0 _refine_ls_number_parameters 127 _oxford_refine_ls_R_factor_ref 0.0165 _refine_ls_wR_factor_ref 0.0162 _refine_ls_goodness_of_fit_ref 1.0936 _refine_ls_shift/su_max 0.004802 # The values computed from all data _oxford_reflns_number_all 7668 _refine_ls_R_factor_all 0.0271 _refine_ls_wR_factor_all 0.0276 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6302 _refine_ls_R_factor_gt 0.0178 _refine_ls_wR_factor_gt 0.0167 # 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: 0.846E-01 0.389E-01 0.295E-01 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached 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 _oxford_atom_site_special_shape _atom_site_attached_hydrogens I1 I 0.633408(11) 0.612808(6) -0.023408(10) 0.0145 1.0000 Uani . . . . . . . I2 I 0.783660(13) 0.471027(6) 0.279823(10) 0.0161 1.0000 Uani . . . . . . . I3 I 0.852140(12) 0.398572(6) -0.081596(10) 0.0151 1.0000 Uani . . . . . . . Cu1 Cu 0.62337(3) 0.463548(16) 0.05518(3) 0.0235 1.0000 Uani . . . . . . . Cu2 Cu 0.89188(3) 0.523793(16) 0.07144(3) 0.0230 1.0000 Uani . . . . . . . C1 C 0.87501(19) 0.70795(10) 0.40977(16) 0.0163 1.0000 Uani . . . . . . . C2 C 1.0407(2) 0.67321(11) 0.41754(19) 0.0206 1.0000 Uani . . . . . . . C3 C 0.8128(2) 0.61603(11) 0.58196(16) 0.0181 1.0000 Uani . . . . . . . C4 C 0.6984(3) 0.55319(13) 0.6165(2) 0.0267 1.0000 Uani . . . . . . . C5 C 0.8411(3) 0.67768(13) 0.68097(18) 0.0250 1.0000 Uani . . . . . . . C6 C 0.8225(3) 0.73159(12) 0.27682(19) 0.0251 1.0000 Uani . . . . . . . C7 C 0.4799(2) 0.64603(13) 0.3517(2) 0.0270 1.0000 Uani . . . . . . . C8 C 0.5907(2) 0.68453(12) 0.45074(19) 0.0220 1.0000 Uani . . . . . . . N9 N 0.75676(16) 0.65094(8) 0.45592(13) 0.0145 1.0000 Uani . . . . . . . H11 H 0.8750 0.7529 0.4637 0.0200 1.0000 Uiso R . . . . . . H23 H 1.0841 0.6658 0.5016 0.0313 1.0000 Uiso R . . . . . . H21 H 1.1080 0.7083 0.3780 0.0323 1.0000 Uiso R . . . . . . H22 H 1.0378 0.6248 0.3753 0.0315 1.0000 Uiso R . . . . . . H31 H 0.9124 0.5909 0.5716 0.0214 1.0000 Uiso R . . . . . . H43 H 0.6757 0.5190 0.5478 0.0416 1.0000 Uiso R . . . . . . H41 H 0.7485 0.5255 0.6859 0.0421 1.0000 Uiso R . . . . . . H42 H 0.6013 0.5762 0.6383 0.0412 1.0000 Uiso R . . . . . . H51 H 0.9200 0.7137 0.6606 0.0374 1.0000 Uiso R . . . . . . H52 H 0.8773 0.6540 0.7581 0.0375 1.0000 Uiso R . . . . . . H53 H 0.7450 0.7047 0.6915 0.0374 1.0000 Uiso R . . . . . . H62 H 0.7193 0.7546 0.2709 0.0376 1.0000 Uiso R . . . . . . H63 H 0.8962 0.7687 0.2502 0.0379 1.0000 Uiso R . . . . . . H61 H 0.8202 0.6874 0.2225 0.0381 1.0000 Uiso R . . . . . . H73 H 0.3770 0.6692 0.3517 0.0400 1.0000 Uiso R . . . . . . H71 H 0.5166 0.6523 0.2710 0.0400 1.0000 Uiso R . . . . . . H72 H 0.4701 0.5929 0.3691 0.0397 1.0000 Uiso R . . . . . . H81 H 0.5954 0.7389 0.4348 0.0268 1.0000 Uiso R . . . . . . H82 H 0.5526 0.6760 0.5295 0.0270 1.0000 Uiso R . . . . . . H91 H 0.7517 0.6117 0.4024 0.0220 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 I1 0.01092(4) 0.01313(4) 0.01919(4) 0.00218(3) -0.00033(3) 0.00003(3) I2 0.01709(4) 0.01777(5) 0.01308(4) 0.00022(3) -0.00067(3) 0.00044(3) I3 0.01223(4) 0.01434(4) 0.01896(4) -0.00456(3) 0.00339(3) -0.00236(3) Cu1 0.01388(9) 0.02693(12) 0.02838(12) 0.00373(9) -0.00413(8) -0.00553(8) Cu2 0.01531(9) 0.02747(12) 0.02684(11) -0.00485(9) 0.00536(8) -0.00745(8) C1 0.0151(6) 0.0148(6) 0.0191(7) -0.0018(5) 0.0016(5) -0.0030(5) C2 0.0159(7) 0.0211(8) 0.0257(8) -0.0010(6) 0.0061(6) -0.0016(6) C3 0.0193(7) 0.0194(7) 0.0155(7) 0.0007(6) 0.0014(5) -0.0014(6) C4 0.0345(10) 0.0259(9) 0.0213(8) 0.0012(7) 0.0104(7) -0.0093(8) C5 0.0287(9) 0.0292(9) 0.0172(7) -0.0050(7) 0.0022(6) -0.0056(7) C6 0.0278(9) 0.0243(9) 0.0225(8) 0.0053(7) -0.0013(7) -0.0041(7) C7 0.0149(7) 0.0276(9) 0.0368(11) -0.0002(8) -0.0054(7) -0.0021(6) C8 0.0131(6) 0.0240(8) 0.0289(9) -0.0044(7) 0.0016(6) 0.0020(6) N9 0.0122(5) 0.0154(6) 0.0157(6) -0.0026(4) 0.0003(4) -0.0012(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.05828(2) 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 I1 . Cu1 2_665 2.5382(3) yes I1 . Cu1 . 2.7280(3) yes I1 . Cu2 . 2.7903(3) yes I2 . Cu1 . 2.6736(3) yes I2 . Cu2 . 2.6764(3) yes I3 . Cu2 2_765 2.5422(3) yes I3 . Cu1 . 2.7841(3) yes I3 . Cu2 . 2.7328(3) yes Cu1 . Cu1 2_665 2.6276(5) yes Cu1 . Cu2 . 2.4900(3) yes Cu2 . Cu2 2_765 2.6378(5) yes C1 . C2 . 1.520(2) yes C1 . C6 . 1.522(3) yes C1 . N9 . 1.524(2) yes C1 . H11 . 0.974 no C2 . H23 . 0.957 no C2 . H21 . 0.961 no C2 . H22 . 0.954 no C3 . C4 . 1.527(3) yes C3 . C5 . 1.517(3) yes C3 . N9 . 1.527(2) yes C3 . H31 . 0.964 no C4 . H43 . 0.957 no C4 . H41 . 0.956 no C4 . H42 . 0.962 no C5 . H51 . 0.955 no C5 . H52 . 0.955 no C5 . H53 . 0.954 no C6 . H62 . 0.956 no C6 . H63 . 0.958 no C6 . H61 . 0.965 no C7 . C8 . 1.511(3) yes C7 . H73 . 0.958 no C7 . H71 . 0.961 no C7 . H72 . 0.946 no C8 . N9 . 1.517(2) yes C8 . H81 . 0.960 no C8 . H82 . 0.951 no N9 . H91 . 0.892 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 Cu1 2_665 I1 . Cu1 . 59.733(10) yes Cu1 2_665 I1 . Cu2 . 113.038(9) yes Cu1 . I1 . Cu2 . 53.630(7) yes Cu1 . I2 . Cu2 . 55.476(8) yes Cu2 2_765 I3 . Cu1 . 113.237(9) yes Cu2 2_765 I3 . Cu2 . 59.878(10) yes Cu1 . I3 . Cu2 . 53.649(7) yes I3 . Cu1 . I1 . 100.015(9) yes I3 . Cu1 . I2 . 100.740(9) yes I1 . Cu1 . I2 . 102.117(9) yes I3 . Cu1 . I1 2_665 110.211(10) yes I1 . Cu1 . I1 2_665 120.267(10) yes I2 . Cu1 . I1 2_665 120.110(11) yes I3 . Cu1 . Cu1 2_665 120.949(16) yes I1 . Cu1 . Cu1 2_665 56.542(10) yes I2 . Cu1 . Cu1 2_665 134.629(18) yes I1 2_665 Cu1 . Cu1 2_665 63.725(9) yes I3 . Cu1 . Cu2 . 62.122(9) yes I1 . Cu1 . Cu2 . 64.466(9) yes I2 . Cu1 . Cu2 . 62.319(9) yes I1 2_665 Cu1 . Cu2 . 172.202(15) yes Cu1 2_665 Cu1 . Cu2 . 120.632(17) yes I1 . Cu2 . I3 . 99.741(9) yes I1 . Cu2 . I2 . 100.425(9) yes I3 . Cu2 . I2 . 102.004(9) yes I1 . Cu2 . I3 2_765 110.907(11) yes I3 . Cu2 . I3 2_765 120.122(10) yes I2 . Cu2 . I3 2_765 120.165(11) yes I1 . Cu2 . Cu2 2_765 121.279(16) yes I3 . Cu2 . Cu2 2_765 56.471(10) yes I2 . Cu2 . Cu2 2_765 134.407(18) yes I3 2_765 Cu2 . Cu2 2_765 63.651(9) yes I1 . Cu2 . Cu1 . 61.904(9) yes I3 . Cu2 . Cu1 . 64.229(9) yes I2 . Cu2 . Cu1 . 62.205(9) yes I3 2_765 Cu2 . Cu1 . 172.706(15) yes Cu2 2_765 Cu2 . Cu1 . 120.366(16) yes C2 . C1 . C6 . 110.08(16) yes C2 . C1 . N9 . 110.79(14) yes C6 . C1 . N9 . 110.10(14) yes C2 . C1 . H11 . 109.6 no C6 . C1 . H11 . 109.6 no N9 . C1 . H11 . 106.5 no C1 . C2 . H23 . 111.9 no C1 . C2 . H21 . 107.8 no H23 . C2 . H21 . 108.6 no C1 . C2 . H22 . 109.9 no H23 . C2 . H22 . 109.2 no H21 . C2 . H22 . 109.4 no C4 . C3 . C5 . 112.98(16) yes C4 . C3 . N9 . 110.62(15) yes C5 . C3 . N9 . 111.56(15) yes C4 . C3 . H31 . 106.7 no C5 . C3 . H31 . 108.7 no N9 . C3 . H31 . 106.0 no C3 . C4 . H43 . 109.7 no C3 . C4 . H41 . 107.9 no H43 . C4 . H41 . 109.9 no C3 . C4 . H42 . 109.8 no H43 . C4 . H42 . 109.6 no H41 . C4 . H42 . 109.9 no C3 . C5 . H51 . 111.3 no C3 . C5 . H52 . 109.3 no H51 . C5 . H52 . 108.1 no C3 . C5 . H53 . 110.6 no H51 . C5 . H53 . 109.2 no H52 . C5 . H53 . 108.2 no C1 . C6 . H62 . 111.0 no C1 . C6 . H63 . 109.0 no H62 . C6 . H63 . 108.4 no C1 . C6 . H61 . 110.5 no H62 . C6 . H61 . 109.0 no H63 . C6 . H61 . 108.9 no C8 . C7 . H73 . 108.4 no C8 . C7 . H71 . 111.3 no H73 . C7 . H71 . 109.0 no C8 . C7 . H72 . 110.4 no H73 . C7 . H72 . 108.2 no H71 . C7 . H72 . 109.5 no C7 . C8 . N9 . 111.46(16) yes C7 . C8 . H81 . 109.8 no N9 . C8 . H81 . 109.2 no C7 . C8 . H82 . 109.2 no N9 . C8 . H82 . 107.3 no H81 . C8 . H82 . 109.8 no C3 . N9 . C1 . 113.15(13) yes C3 . N9 . C8 . 113.12(14) yes C1 . N9 . C8 . 111.90(14) yes C3 . N9 . H91 . 105.7 no C1 . N9 . H91 . 105.9 no C8 . N9 . H91 . 106.4 no