# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Catherine E. Housecroft' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Edwin Constable' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Markus Neuburger' '' '' 'Silvia Schaffner' '' '' 'Guoqi Zhang.' '' '' _publ_contact_author_name 'Catherine E. Housecroft ' _publ_contact_author_email CATHERINE.HOUSECROFT@UNIBAS.CH _publ_section_title ; Hierarchical multicomponent assembly utilizing sequential metal-ligand and hydrogen-bonding interactions ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' _publ_requested_journal 'Section E' # Attachment 'gq19_2_123.cif' data_gq19_2_123k _database_code_depnum_ccdc_archive 'CCDC 704884' _audit_creation_date 08-09-01 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'gq19_2_123k_0m in P2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 16.2898(8) _cell_length_b 7.7309(4) _cell_length_c 22.0964(11) _cell_angle_alpha 90 _cell_angle_beta 104.532(2) _cell_angle_gamma 90 _cell_volume 2693.7(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Gd -0.1653 3.9035 25.0709 2.2534 19.0798 0.1820 13.8518 12.9331 3.5454 101.3980 2.4196 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C48 H66 Cl3 Cu2 Gd1 N4 O9 # Dc = 1.52 Fooo = 1252.00 Mu = 22.02 M = 1233.77 # Found Formula = C60 H68 Cu2 N4 O14 # Dc = 1.47 FOOO = 1252.00 Mu = 8.63 M = 1196.31 _chemical_formula_sum 'C60 H68 Cu2 N4 O14' _chemical_formula_moiety '2(C24 H28 Cu N2 O4), C12 H8 O4, 2(H2 O)' _chemical_compound_source ? _chemical_formula_weight 1196.31 _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 brown _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1252 _exptl_absorpt_coefficient_mu 0.863 # Sheldrick geometric approximatio 0.95 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.97 # 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_type 'Nonius KappaCCD' _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 28759 _reflns_number_total 12470 _diffrn_reflns_av_R_equivalents 0.034 # Number of reflections with Friedels Law is 6909 # Number of reflections without Friedels Law is 12470 # Theoretical number of reflections is about 6536 _diffrn_reflns_theta_min 2.015 _diffrn_reflns_theta_max 28.075 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.268 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _reflns_limit_h_min -21 _reflns_limit_h_max 20 _reflns_limit_k_min -9 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _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 -0.52 _refine_diff_density_max 0.34 _refine_ls_number_reflns 7434 _refine_ls_number_restraints 35 _refine_ls_number_parameters 740 #_refine_ls_R_factor_ref 0.0300 _refine_ls_wR_factor_ref 0.0310 _refine_ls_goodness_of_fit_ref 1.1162 #_reflns_number_all 12441 _refine_ls_R_factor_all 0.0667 _refine_ls_wR_factor_all 0.0558 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 7434 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_gt 0.0310 _refine_ls_shift/su_max 0.000268 _refine_ls_abs_structure_Flack 0.010(12) _refine_ls_abs_structure_details 'Flack (1983), 5561 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: 0.625 -0.247E-01 0.339 ; _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_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 Fih. ; ? ; _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. ; _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 ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. 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 _atom_site_attached_hydrogens Cu1 Cu 0.73276(5) 0.14093(10) 0.71286(3) 0.0158 1.0000 Uani . . . . . . Cu2 Cu 0.76657(4) 0.73631(10) -0.21017(3) 0.0143 1.0000 Uani . . . . . . N1 N 0.7872(3) 0.2550(5) 0.79073(17) 0.0190 1.0000 Uani . . . . . . N2 N 0.6380(3) 0.1144(4) 0.75053(17) 0.0196 1.0000 Uani . . . . . . N3 N 0.8660(3) 0.7106(4) -0.24327(16) 0.0152 1.0000 Uani . . . . . . N4 N 0.7048(3) 0.6738(5) -0.29558(17) 0.0184 1.0000 Uani . . . . . . C1 C 0.9103(4) 0.1815(6) 0.7173(2) 0.0165 1.0000 Uani . . . . . . C2 C 0.9804(4) 0.1625(6) 0.6884(2) 0.0209 1.0000 Uani . . . . . . C3 C 1.0597(4) 0.2247(6) 0.7168(2) 0.0242 1.0000 Uani . . . . . . C4 C 1.0754(5) 0.3060(7) 0.7754(3) 0.0289 1.0000 Uani . . . . . . C5 C 1.0117(4) 0.3268(7) 0.8043(3) 0.0257 1.0000 Uani . . . . . . C6 C 0.9277(4) 0.2637(6) 0.7765(2) 0.0189 1.0000 Uani . . . . . . C7 C 0.8657(4) 0.2913(6) 0.8105(2) 0.0208 1.0000 Uani . . . . . . C8 C 0.7252(2) 0.2972(5) 0.82812(16) 0.0203 1.0000 Uani . . . . . . C9 C 0.7619(4) 0.3355(7) 0.8974(2) 0.0286 1.0000 Uani . . . . . . C10 C 0.6896(3) 0.3722(5) 0.92892(18) 0.0319 1.0000 Uani . . . . . . C11 C 0.6243(3) 0.2298(6) 0.91796(17) 0.0358 1.0000 Uani . . . . . . C12 C 0.5885(4) 0.1899(6) 0.8483(2) 0.0290 1.0000 Uani . . . . . . C13 C 0.6624(2) 0.1520(5) 0.81867(14) 0.0214 1.0000 Uani . . . . . . C14 C 0.5619(4) 0.0701(6) 0.7223(2) 0.0201 1.0000 Uani . . . . . . C15 C 0.5335(4) 0.0174(7) 0.6579(3) 0.0211 1.0000 Uani . . . . . . C16 C 0.4512(4) -0.0488(7) 0.6369(3) 0.0262 1.0000 Uani . . . . . . C17 C 0.4206(4) -0.1161(7) 0.5797(3) 0.0272 1.0000 Uani . . . . . . C18 C 0.4751(4) -0.1226(6) 0.5389(2) 0.0205 1.0000 Uani . . . . . . C19 C 0.5568(4) -0.0590(7) 0.5565(2) 0.0190 1.0000 Uani . . . . . . C20 C 0.5900(4) 0.0170(6) 0.6175(2) 0.0161 1.0000 Uani . . . . . . C21 C 1.0275(3) 0.0548(6) 0.6011(2) 0.0298 1.0000 Uani . . . . . . C22 C 0.9936(4) -0.0533(7) 0.5438(2) 0.0364 1.0000 Uani . . . . . . C23 C 0.5843(4) -0.1482(7) 0.4606(2) 0.0241 1.0000 Uani . . . . . . C24 C 0.6550(4) -0.1301(7) 0.4275(3) 0.0272 1.0000 Uani . . . . . . C31 C 0.9093(4) 0.8787(6) -0.1193(2) 0.0172 1.0000 Uani . . . . . . C32 C 0.9428(4) 0.9653(6) -0.0617(2) 0.0178 1.0000 Uani . . . . . . C33 C 1.0217(4) 1.0363(6) -0.0469(2) 0.0226 1.0000 Uani . . . . . . C34 C 1.0747(4) 1.0170(7) -0.0865(3) 0.0241 1.0000 Uani . . . . . . C35 C 1.0474(4) 0.9269(7) -0.1419(3) 0.0201 1.0000 Uani . . . . . . C36 C 0.9634(4) 0.8586(7) -0.1587(2) 0.0177 1.0000 Uani . . . . . . C37 C 0.9397(4) 0.7711(6) -0.2183(2) 0.0174 1.0000 Uani . . . . . . C38 C 0.8454(2) 0.6189(4) -0.30381(15) 0.0181 1.0000 Uani . . . . . . C39 C 0.9115(3) 0.6315(6) -0.3424(2) 0.0236 1.0000 Uani . . . . . . C40 C 0.8799(3) 0.5284(5) -0.40310(16) 0.0279 1.0000 Uani . . . . . . C41 C 0.7925(3) 0.5910(5) -0.43935(17) 0.0278 1.0000 Uani . . . . . . C42 C 0.7273(4) 0.5792(7) -0.4003(2) 0.0244 1.0000 Uani . . . . . . C43 C 0.7585(2) 0.6824(5) -0.33991(15) 0.0182 1.0000 Uani . . . . . . C44 C 0.6271(4) 0.6255(7) -0.3111(2) 0.0230 1.0000 Uani . . . . . . C45 C 0.5680(4) 0.6223(7) -0.2710(3) 0.0221 1.0000 Uani . . . . . . C46 C 0.4861(4) 0.5673(8) -0.2981(3) 0.0330 1.0000 Uani . . . . . . C47 C 0.4249(4) 0.5671(8) -0.2658(3) 0.0353 1.0000 Uani . . . . . . C48 C 0.4448(4) 0.6260(7) -0.2041(3) 0.0303 1.0000 Uani . . . . . . C49 C 0.5255(3) 0.6803(6) -0.1766(2) 0.0229 1.0000 Uani . . . . . . C50 C 0.5914(4) 0.6800(6) -0.2083(2) 0.0176 1.0000 Uani . . . . . . C51 C 0.9112(4) 1.0647(7) 0.0329(2) 0.0261 1.0000 Uani . . . . . . C52 C 0.8428(4) 1.0497(7) 0.0671(2) 0.0280 1.0000 Uani . . . . . . C53 C 0.4751(6) 0.7757(13) -0.0940(5) 0.0301 0.5000 Uani D U . . . . C54 C 0.5040(8) 0.8762(13) -0.0349(5) 0.0362 0.5000 Uani D U . . . . C63 C 0.5072(5) 0.7094(10) -0.0671(3) 0.0298 0.5000 Uani D U . . . . C64 C 0.4527(6) 0.8665(11) -0.0690(4) 0.0358 0.5000 Uani D U . . . . C81 C 0.7079(4) 0.6420(7) 0.1605(2) 0.0217 1.0000 Uani . . . . . . C82 C 0.6909(4) 0.7279(7) 0.2132(3) 0.0304 1.0000 Uani . . . . . . C83 C 0.7059(5) 0.6481(8) 0.2695(3) 0.0331 1.0000 Uani . . . . . . C84 C 0.7414(4) 0.4781(7) 0.2774(3) 0.0214 1.0000 Uani . . . . . . C85 C 0.7600(4) 0.3921(7) 0.3363(2) 0.0217 1.0000 Uani . . . . . . C86 C 0.7952(4) 0.2284(7) 0.3426(2) 0.0218 1.0000 Uani . . . . . . C87 C 0.8128(4) 0.1468(7) 0.2903(2) 0.0257 1.0000 Uani . . . . . . C88 C 0.7936(4) 0.2255(7) 0.2334(2) 0.0241 1.0000 Uani . . . . . . C89 C 0.7589(4) 0.3928(7) 0.2249(2) 0.0185 1.0000 Uani . . . . . . C90 C 0.7407(4) 0.4796(7) 0.1673(3) 0.0207 1.0000 Uani . . . . . . C91 C 0.6919(4) 0.7430(8) 0.1009(3) 0.0254 1.0000 Uani . . . . . . C92 C 0.8132(4) 0.1348(8) 0.4034(2) 0.0229 1.0000 Uani . . . . . . O1 O 0.8357(3) 0.1289(5) 0.68661(16) 0.0186 1.0000 Uani . . . . . . O2 O 0.6686(3) 0.0712(4) 0.63169(15) 0.0166 1.0000 Uani . . . . . . O3 O 0.8308(3) 0.8194(4) -0.13108(16) 0.0189 1.0000 Uani . . . . . . O4 O 0.6675(2) 0.7326(5) -0.17848(16) 0.0181 1.0000 Uani . . . . . . O5 O 0.9594(2) 0.0829(4) 0.63153(14) 0.0223 1.0000 Uani . . . . . . O6 O 0.8856(3) 0.9722(5) -0.02440(16) 0.0225 1.0000 Uani . . . . . . O7 O 0.6122(2) -0.0596(4) 0.51950(16) 0.0185 1.0000 Uani . . . . . . O8 O 0.5517(2) 0.7403(5) -0.11602(16) 0.0373 1.0000 Uani D U . . . . O11 O 0.8394(3) -0.0128(5) 0.40791(19) 0.0369 1.0000 Uani . . . . . . O12 O 0.7949(3) 0.2255(5) 0.44930(16) 0.0269 1.0000 Uani . . . . . . O13 O 0.7140(3) 0.6568(5) 0.05557(16) 0.0247 1.0000 Uani . . . . . . O14 O 0.6630(3) 0.8883(6) 0.0951(2) 0.0415 1.0000 Uani . . . . . . O51 O 0.7184(3) 0.8193(5) -0.04590(17) 0.0263 1.0000 Uani . . . . . . O52 O 0.7874(3) 0.0679(5) 0.55075(17) 0.0251 1.0000 Uani . . . . . . H1 H 0.8055 0.1723 0.4824 0.0205 1.0000 Uiso R . . . . . H2 H 0.7173 0.7136 0.0250 0.0291 1.0000 Uiso R . . . . . H3 H 0.6861 0.7881 -0.0786 0.0350 1.0000 Uiso R . . . . . H4 H 0.7599 0.8607 -0.0555 0.0420 1.0000 Uiso R . . . . . H5 H 0.8236 0.0779 0.5838 0.0351 1.0000 Uiso R . . . . . H6 H 0.7417 0.0741 0.5600 0.0278 1.0000 Uiso R . . . . . H31 H 1.1048 0.2127 0.6963 0.0297 1.0000 Uiso R . . . . . H41 H 1.1314 0.3472 0.7950 0.0306 1.0000 Uiso R . . . . . H51 H 1.0229 0.3838 0.8441 0.0298 1.0000 Uiso R . . . . . H71 H 0.8838 0.3421 0.8513 0.0229 1.0000 Uiso R . . . . . H81 H 0.6948 0.3986 0.8098 0.0239 1.0000 Uiso R . . . . . H91 H 0.7980 0.4353 0.9017 0.0321 1.0000 Uiso R . . . . . H92 H 0.7943 0.2378 0.9170 0.0321 1.0000 Uiso R . . . . . H101 H 0.7134 0.3831 0.9731 0.0391 1.0000 Uiso R . . . . . H102 H 0.6622 0.4786 0.9128 0.0391 1.0000 Uiso R . . . . . H111 H 0.5786 0.2642 0.9356 0.0455 1.0000 Uiso R . . . . . H112 H 0.6502 0.1266 0.9384 0.0455 1.0000 Uiso R . . . . . H121 H 0.5569 0.2878 0.8281 0.0357 1.0000 Uiso R . . . . . H122 H 0.5518 0.0909 0.8437 0.0357 1.0000 Uiso R . . . . . H131 H 0.6915 0.0521 0.8394 0.0270 1.0000 Uiso R . . . . . H141 H 0.5204 0.0713 0.7464 0.0265 1.0000 Uiso R . . . . . H161 H 0.4147 -0.0451 0.6648 0.0310 1.0000 Uiso R . . . . . H171 H 0.3636 -0.1596 0.5673 0.0338 1.0000 Uiso R . . . . . H181 H 0.4546 -0.1719 0.4980 0.0246 1.0000 Uiso R . . . . . H211 H 1.0482 0.1634 0.5899 0.0367 1.0000 Uiso R . . . . . H212 H 1.0729 -0.0064 0.6290 0.0367 1.0000 Uiso R . . . . . H221 H 1.0378 -0.0746 0.5231 0.0455 1.0000 Uiso R . . . . . H222 H 0.9481 0.0083 0.5162 0.0455 1.0000 Uiso R . . . . . H223 H 0.9729 -0.1615 0.5553 0.0455 1.0000 Uiso R . . . . . H231 H 0.5330 -0.0970 0.4361 0.0289 1.0000 Uiso R . . . . . H232 H 0.5747 -0.2683 0.4674 0.0289 1.0000 Uiso R . . . . . H241 H 0.6388 -0.1878 0.3878 0.0306 1.0000 Uiso R . . . . . H242 H 0.6645 -0.0097 0.4211 0.0306 1.0000 Uiso R . . . . . H243 H 0.7061 -0.1810 0.4524 0.0306 1.0000 Uiso R . . . . . H331 H 1.0406 1.1004 -0.0088 0.0247 1.0000 Uiso R . . . . . H341 H 1.1308 1.0655 -0.0750 0.0298 1.0000 Uiso R . . . . . H351 H 1.0845 0.9107 -0.1690 0.0272 1.0000 Uiso R . . . . . H371 H 0.9826 0.7581 -0.2409 0.0222 1.0000 Uiso R . . . . . H381 H 0.8396 0.4985 -0.2951 0.0217 1.0000 Uiso R . . . . . H391 H 0.9645 0.5847 -0.3187 0.0316 1.0000 Uiso R . . . . . H392 H 0.9192 0.7505 -0.3521 0.0316 1.0000 Uiso R . . . . . H401 H 0.9193 0.5428 -0.4285 0.0352 1.0000 Uiso R . . . . . H402 H 0.8764 0.4082 -0.3932 0.0352 1.0000 Uiso R . . . . . H411 H 0.7970 0.7093 -0.4513 0.0354 1.0000 Uiso R . . . . . H412 H 0.7736 0.5211 -0.4761 0.0354 1.0000 Uiso R . . . . . H421 H 0.7193 0.4603 -0.3906 0.0276 1.0000 Uiso R . . . . . H422 H 0.6743 0.6268 -0.4235 0.0276 1.0000 Uiso R . . . . . H431 H 0.7637 0.8015 -0.3507 0.0234 1.0000 Uiso R . . . . . H441 H 0.6050 0.5885 -0.3535 0.0254 1.0000 Uiso R . . . . . H461 H 0.4720 0.5283 -0.3407 0.0359 1.0000 Uiso R . . . . . H471 H 0.3689 0.5258 -0.2852 0.0421 1.0000 Uiso R . . . . . H481 H 0.4018 0.6299 -0.1813 0.0378 1.0000 Uiso R . . . . . H511 H 0.9628 1.0158 0.0580 0.0301 1.0000 Uiso R . . . . . H512 H 0.9204 1.1840 0.0246 0.0301 1.0000 Uiso R . . . . . H521 H 0.8592 1.1114 0.1059 0.0324 1.0000 Uiso R . . . . . H522 H 0.8338 0.9301 0.0751 0.0324 1.0000 Uiso R . . . . . H523 H 0.7914 1.0983 0.0417 0.0324 1.0000 Uiso R . . . . . H531 H 0.4356 0.8430 -0.1245 0.0337 0.5000 Uiso R . . . . . H532 H 0.4487 0.6694 -0.0867 0.0337 0.5000 Uiso R . . . . . H541 H 0.4560 0.9029 -0.0188 0.0515 0.5000 Uiso R . . . . . H542 H 0.5308 0.9816 -0.0428 0.0515 0.5000 Uiso R . . . . . H543 H 0.5438 0.8080 -0.0049 0.0515 0.5000 Uiso R . . . . . H631 H 0.5465 0.6980 -0.0269 0.0342 0.5000 Uiso R . . . . . H632 H 0.4727 0.6072 -0.0759 0.0342 0.5000 Uiso R . . . . . H641 H 0.4210 0.8564 -0.0380 0.0465 0.5000 Uiso R . . . . . H642 H 0.4881 0.9674 -0.0606 0.0465 0.5000 Uiso R . . . . . H643 H 0.4144 0.8766 -0.1096 0.0465 0.5000 Uiso R . . . . . H821 H 0.6689 0.8437 0.2087 0.0385 1.0000 Uiso R . . . . . H831 H 0.6926 0.7063 0.3043 0.0418 1.0000 Uiso R . . . . . H851 H 0.7481 0.4484 0.3719 0.0270 1.0000 Uiso R . . . . . H871 H 0.8387 0.0344 0.2949 0.0323 1.0000 Uiso R . . . . . H881 H 0.8041 0.1652 0.1981 0.0310 1.0000 Uiso R . . . . . H901 H 0.7519 0.4228 0.1316 0.0255 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 0.0210(4) 0.0151(3) 0.0117(3) 0.0000(2) 0.0050(3) 0.0022(3) Cu2 0.0173(4) 0.0142(3) 0.0127(3) -0.0012(2) 0.0064(3) 0.0000(3) N1 0.027(2) 0.0153(19) 0.0133(15) 0.0004(13) 0.0029(14) 0.0028(15) N2 0.032(2) 0.0133(18) 0.0161(16) 0.0006(13) 0.0111(15) 0.0022(15) N3 0.0202(19) 0.0119(17) 0.0152(15) 0.0013(12) 0.0076(13) 0.0044(14) N4 0.028(2) 0.0150(19) 0.0138(15) 0.0045(12) 0.0080(14) 0.0033(14) C1 0.016(2) 0.016(2) 0.0178(19) 0.0061(15) 0.0049(17) 0.0028(17) C2 0.029(2) 0.0097(19) 0.0223(19) 0.0016(16) 0.0028(16) 0.0013(17) C3 0.021(2) 0.022(2) 0.029(2) 0.0062(19) 0.0045(18) -0.0013(19) C4 0.027(3) 0.022(2) 0.031(2) 0.0034(19) -0.004(2) -0.002(2) C5 0.027(3) 0.026(3) 0.019(2) -0.0002(19) -0.004(2) -0.001(2) C6 0.029(3) 0.010(2) 0.015(2) 0.0031(17) 0.000(2) -0.001(2) C7 0.033(3) 0.0126(19) 0.0144(19) 0.0010(15) 0.0018(18) 0.0022(18) C8 0.032(2) 0.0158(17) 0.0137(15) -0.0012(13) 0.0078(15) 0.0082(16) C9 0.045(3) 0.022(2) 0.018(2) -0.0016(17) 0.007(2) 0.008(2) C10 0.058(3) 0.021(2) 0.0175(18) -0.0034(16) 0.0112(19) 0.014(2) C11 0.060(3) 0.031(2) 0.0237(17) -0.0016(18) 0.0224(18) 0.010(2) C12 0.043(3) 0.023(2) 0.025(2) 0.0000(17) 0.016(2) 0.0039(19) C13 0.038(2) 0.0129(17) 0.0165(14) 0.0011(15) 0.0137(14) 0.0034(17) C14 0.026(3) 0.014(2) 0.025(2) 0.0049(17) 0.0153(19) 0.0023(18) C15 0.023(4) 0.019(3) 0.022(3) 0.002(2) 0.006(2) 0.008(2) C16 0.015(3) 0.028(3) 0.038(3) 0.007(2) 0.013(3) -0.001(2) C17 0.020(3) 0.030(3) 0.031(3) 0.001(2) 0.005(2) -0.001(2) C18 0.018(2) 0.024(2) 0.018(2) 0.0003(17) 0.0026(17) 0.0015(18) C19 0.020(3) 0.021(2) 0.017(2) 0.0047(16) 0.0059(19) -0.0006(18) C20 0.020(3) 0.011(2) 0.020(2) 0.0022(17) 0.009(2) 0.0049(19) C21 0.021(2) 0.036(3) 0.035(2) 0.000(2) 0.0125(19) 0.0050(19) C22 0.038(3) 0.044(3) 0.034(2) -0.002(2) 0.023(2) 0.001(2) C23 0.025(3) 0.032(3) 0.014(2) -0.0070(17) 0.0018(17) -0.003(2) C24 0.025(3) 0.035(3) 0.022(2) -0.0080(18) 0.0053(19) 0.008(2) C31 0.018(3) 0.013(2) 0.019(2) 0.0033(17) 0.002(2) -0.0053(19) C32 0.020(3) 0.014(2) 0.021(2) 0.0031(16) 0.0084(19) 0.0051(17) C33 0.027(3) 0.014(2) 0.023(2) 0.0024(15) 0.0008(18) -0.0048(18) C34 0.018(3) 0.023(2) 0.032(3) 0.0032(19) 0.008(2) -0.0070(19) C35 0.023(4) 0.020(3) 0.020(2) 0.0013(19) 0.010(2) -0.002(2) C36 0.019(3) 0.017(3) 0.020(3) 0.005(2) 0.010(2) -0.003(2) C37 0.022(2) 0.011(2) 0.0215(19) 0.0032(15) 0.0109(17) 0.0014(16) C38 0.0275(19) 0.0123(18) 0.0167(15) 0.0000(13) 0.0096(14) 0.0015(14) C39 0.033(2) 0.024(2) 0.0204(18) 0.0002(17) 0.0175(16) 0.005(2) C40 0.048(3) 0.0209(19) 0.0198(17) -0.0014(15) 0.0173(18) 0.0055(17) C41 0.048(3) 0.021(2) 0.0162(17) 0.0003(14) 0.0113(17) 0.0092(18) C42 0.035(3) 0.022(2) 0.013(2) 0.0004(15) 0.0006(18) 0.0040(19) C43 0.0275(19) 0.0153(17) 0.0126(15) 0.0030(12) 0.0065(14) 0.0040(14) C44 0.028(3) 0.024(2) 0.0143(19) 0.0045(19) 0.0008(17) -0.003(2) C45 0.014(3) 0.027(3) 0.025(2) 0.009(2) 0.004(2) 0.003(2) C46 0.033(4) 0.040(3) 0.020(2) 0.008(2) -0.006(2) -0.009(3) C47 0.013(3) 0.048(3) 0.040(3) 0.020(2) -0.003(2) -0.008(2) C48 0.023(3) 0.026(2) 0.045(3) 0.008(2) 0.015(2) 0.0027(19) C49 0.017(2) 0.019(2) 0.036(2) 0.0038(17) 0.0128(18) -0.0013(16) C50 0.021(3) 0.010(2) 0.020(2) 0.0036(15) 0.0018(17) 0.0013(17) C51 0.032(3) 0.026(2) 0.018(2) -0.0048(18) 0.0022(19) -0.003(2) C52 0.034(3) 0.035(3) 0.015(2) -0.0088(18) 0.0053(19) -0.011(2) C53 0.026(4) 0.030(4) 0.043(4) 0.000(4) 0.025(4) 0.001(3) C54 0.028(5) 0.041(5) 0.049(5) -0.007(4) 0.028(4) -0.014(4) C63 0.028(4) 0.041(4) 0.024(3) 0.006(3) 0.014(3) -0.001(3) C64 0.025(4) 0.048(5) 0.035(4) 0.006(4) 0.010(4) 0.008(4) C81 0.022(3) 0.026(3) 0.018(2) 0.006(2) 0.008(2) -0.001(2) C82 0.044(4) 0.019(2) 0.032(3) -0.002(2) 0.016(3) 0.014(3) C83 0.047(5) 0.034(3) 0.026(2) 0.001(3) 0.024(3) 0.002(3) C84 0.019(3) 0.023(3) 0.024(3) -0.001(2) 0.009(2) 0.001(2) C85 0.024(4) 0.028(3) 0.015(2) 0.003(2) 0.008(2) -0.001(2) C86 0.019(3) 0.024(2) 0.027(2) 0.003(2) 0.013(2) 0.000(2) C87 0.030(4) 0.026(3) 0.026(2) 0.007(2) 0.016(2) 0.007(2) C88 0.030(4) 0.022(3) 0.023(2) 0.000(2) 0.013(2) 0.011(3) C89 0.020(3) 0.020(3) 0.020(2) 0.001(2) 0.012(2) 0.001(2) C90 0.018(3) 0.026(3) 0.022(2) -0.006(2) 0.012(2) 0.003(2) C91 0.021(3) 0.029(3) 0.029(3) -0.001(2) 0.012(2) 0.000(3) C92 0.020(3) 0.030(3) 0.020(2) 0.008(2) 0.007(2) 0.002(2) O1 0.0173(19) 0.0219(17) 0.0167(14) -0.0036(13) 0.0045(12) 0.0013(14) O2 0.015(2) 0.0208(17) 0.0153(17) -0.0013(13) 0.0054(15) -0.0005(15) O3 0.020(2) 0.0225(19) 0.0160(17) -0.0036(14) 0.0068(16) -0.0030(16) O4 0.0189(19) 0.0181(15) 0.0182(14) -0.0026(13) 0.0064(13) -0.0034(15) O5 0.0188(14) 0.0264(16) 0.0232(14) 0.0008(11) 0.0078(11) 0.0018(12) O6 0.0240(19) 0.0270(17) 0.0171(15) -0.0048(12) 0.0065(13) -0.0047(13) O7 0.0204(18) 0.0244(16) 0.0116(14) -0.0042(11) 0.0058(13) -0.0026(13) O8 0.0381(19) 0.0413(19) 0.0438(19) -0.0213(17) 0.0313(16) -0.0193(17) O11 0.054(3) 0.032(2) 0.029(2) 0.0093(18) 0.018(2) 0.012(2) O12 0.035(2) 0.0288(19) 0.0172(15) 0.0038(15) 0.0078(14) 0.0042(17) O13 0.029(2) 0.0271(18) 0.0209(15) 0.0046(15) 0.0118(14) 0.0035(16) O14 0.055(4) 0.038(2) 0.041(2) 0.015(2) 0.029(2) 0.029(2) O51 0.033(2) 0.0288(19) 0.0167(16) -0.0009(14) 0.0062(15) -0.0077(16) O52 0.021(2) 0.040(2) 0.0173(16) 0.0014(15) 0.0099(15) -0.0034(16) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3088(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 Cu1 . N1 . 1.939(4) yes Cu1 . N2 . 1.940(4) yes Cu1 . O1 . 1.910(4) yes Cu1 . O2 . 1.913(3) yes Cu2 . N3 . 1.947(4) yes Cu2 . N4 . 1.963(4) yes Cu2 . O3 . 1.909(3) yes Cu2 . O4 . 1.913(4) yes N1 . C7 . 1.274(7) yes N1 . C8 . 1.494(5) yes N2 . C13 . 1.486(5) yes N2 . C14 . 1.286(7) yes N3 . C37 . 1.278(6) yes N3 . C38 . 1.476(5) yes N4 . C43 . 1.469(5) yes N4 . C44 . 1.281(7) yes C1 . C2 . 1.448(8) yes C1 . C6 . 1.418(7) yes C1 . O1 . 1.299(6) yes C2 . C3 . 1.373(7) yes C2 . O5 . 1.363(6) yes C3 . C4 . 1.405(8) yes C3 . H31 . 0.960 no C4 . C5 . 1.358(10) yes C4 . H41 . 0.960 no C5 . C6 . 1.437(8) yes C5 . H51 . 0.960 no C6 . C7 . 1.418(9) yes C7 . H71 . 0.960 no C8 . C9 . 1.526(6) yes C8 . C13 . 1.498(5) yes C8 . H81 . 0.960 no C9 . C10 . 1.538(8) yes C9 . H91 . 0.960 no C9 . H92 . 0.960 no C10 . C11 . 1.508(6) yes C10 . H101 . 0.960 no C10 . H102 . 0.960 no C11 . C12 . 1.534(6) yes C11 . H111 . 0.960 no C11 . H112 . 0.960 no C12 . C13 . 1.536(6) yes C12 . H121 . 0.960 no C12 . H122 . 0.960 no C13 . H131 . 0.960 no C14 . C15 . 1.440(7) yes C14 . H141 . 0.960 no C15 . C16 . 1.401(9) yes C15 . C20 . 1.434(9) yes C16 . C17 . 1.342(9) yes C16 . H161 . 0.960 no C17 . C18 . 1.416(9) yes C17 . H171 . 0.960 no C18 . C19 . 1.379(8) yes C18 . H181 . 0.960 no C19 . C20 . 1.445(7) yes C19 . O7 . 1.363(7) yes C20 . O2 . 1.307(7) yes C21 . C22 . 1.501(7) yes C21 . O5 . 1.451(6) yes C21 . H211 . 0.960 no C21 . H212 . 0.960 no C22 . H221 . 0.960 no C22 . H222 . 0.960 no C22 . H223 . 0.960 no C23 . C24 . 1.517(9) yes C23 . O7 . 1.440(6) yes C23 . H231 . 0.960 no C23 . H232 . 0.960 no C24 . H241 . 0.960 no C24 . H242 . 0.960 no C24 . H243 . 0.960 no C31 . C32 . 1.421(7) yes C31 . C36 . 1.395(9) yes C31 . O3 . 1.320(7) yes C32 . C33 . 1.359(8) yes C32 . O6 . 1.391(7) yes C33 . C34 . 1.383(9) yes C33 . H331 . 0.960 no C34 . C35 . 1.381(8) yes C34 . H341 . 0.960 no C35 . C36 . 1.427(8) yes C35 . H351 . 0.960 no C36 . C37 . 1.444(7) yes C37 . H371 . 0.960 no C38 . C39 . 1.535(6) yes C38 . C43 . 1.521(5) yes C38 . H381 . 0.960 no C39 . C40 . 1.535(6) yes C39 . H391 . 0.960 no C39 . H392 . 0.960 no C40 . C41 . 1.526(6) yes C40 . H401 . 0.960 no C40 . H402 . 0.960 no C41 . C42 . 1.530(8) yes C41 . H411 . 0.960 no C41 . H412 . 0.960 no C42 . C43 . 1.528(6) yes C42 . H421 . 0.960 no C42 . H422 . 0.960 no C43 . H431 . 0.960 no C44 . C45 . 1.463(9) yes C44 . H441 . 0.960 no C45 . C46 . 1.386(8) yes C45 . C50 . 1.414(7) yes C46 . C47 . 1.363(10) yes C46 . H461 . 0.960 no C47 . C48 . 1.396(9) yes C47 . H471 . 0.960 no C48 . C49 . 1.369(8) yes C48 . H481 . 0.960 no C49 . C50 . 1.420(8) yes C49 . O8 . 1.379(6) yes C50 . O4 . 1.315(6) yes C51 . C52 . 1.498(9) yes C51 . O6 . 1.423(6) yes C51 . H511 . 0.960 no C51 . H512 . 0.960 no C52 . H521 . 0.960 no C52 . H522 . 0.960 no C52 . H523 . 0.960 no C53 . C54 . 1.490(8) yes C53 . O8 . 1.475(8) yes C53 . H531 . 0.960 no C53 . H532 . 0.960 no C54 . H541 . 0.960 no C54 . H542 . 0.960 no C54 . H543 . 0.960 no C63 . C64 . 1.498(8) yes C63 . O8 . 1.465(6) yes C63 . H631 . 0.960 no C63 . H632 . 0.960 no C64 . H641 . 0.960 no C64 . H642 . 0.960 no C64 . H643 . 0.960 no C81 . C82 . 1.425(8) yes C81 . C90 . 1.358(8) yes C81 . C91 . 1.497(7) yes C82 . C83 . 1.356(8) yes C82 . H821 . 0.960 no C83 . C84 . 1.429(8) yes C83 . H831 . 0.960 no C84 . C85 . 1.424(7) yes C84 . C89 . 1.425(4) yes C85 . C86 . 1.382(8) yes C85 . H851 . 0.960 no C86 . C87 . 1.409(8) yes C86 . C92 . 1.489(7) yes C87 . C88 . 1.359(7) yes C87 . H871 . 0.960 no C88 . C89 . 1.405(7) yes C88 . H881 . 0.960 no C89 . C90 . 1.403(7) yes C90 . H901 . 0.960 no C91 . O13 . 1.327(7) yes C91 . O14 . 1.212(7) yes C92 . O11 . 1.213(7) yes C92 . O12 . 1.326(7) yes O12 . H1 . 0.819 no O13 . H2 . 0.819 no O51 . H3 . 0.817 no O51 . H4 . 0.821 no O52 . H5 . 0.820 no O52 . H6 . 0.821 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 . Cu1 . N2 . 84.48(18) yes N1 . Cu1 . O1 . 92.89(17) yes N2 . Cu1 . O1 . 168.35(16) yes N1 . Cu1 . O2 . 168.80(16) yes N2 . Cu1 . O2 . 93.77(16) yes O1 . Cu1 . O2 . 90.95(16) yes N3 . Cu2 . N4 . 83.55(17) yes N3 . Cu2 . O3 . 93.52(17) yes N4 . Cu2 . O3 . 173.61(16) yes N3 . Cu2 . O4 . 173.26(15) yes N4 . Cu2 . O4 . 94.16(17) yes O3 . Cu2 . O4 . 89.37(17) yes Cu1 . N1 . C7 . 126.9(4) yes Cu1 . N1 . C8 . 111.6(3) yes C7 . N1 . C8 . 121.5(4) yes Cu1 . N2 . C13 . 112.0(3) yes Cu1 . N2 . C14 . 126.4(3) yes C13 . N2 . C14 . 121.6(4) yes Cu2 . N3 . C37 . 125.5(3) yes Cu2 . N3 . C38 . 111.6(3) yes C37 . N3 . C38 . 122.8(4) yes Cu2 . N4 . C43 . 112.5(3) yes Cu2 . N4 . C44 . 124.2(3) yes C43 . N4 . C44 . 123.2(4) yes C2 . C1 . C6 . 117.1(5) yes C2 . C1 . O1 . 118.4(5) yes C6 . C1 . O1 . 124.4(5) yes C1 . C2 . C3 . 121.2(5) yes C1 . C2 . O5 . 114.2(5) yes C3 . C2 . O5 . 124.7(5) yes C2 . C3 . C4 . 120.8(6) yes C2 . C3 . H31 . 119.6 no C4 . C3 . H31 . 119.6 no C3 . C4 . C5 . 120.1(6) yes C3 . C4 . H41 . 119.8 no C5 . C4 . H41 . 120.1 no C4 . C5 . C6 . 121.1(5) yes C4 . C5 . H51 . 119.6 no C6 . C5 . H51 . 119.3 no C5 . C6 . C1 . 119.7(6) yes C5 . C6 . C7 . 116.8(5) yes C1 . C6 . C7 . 123.5(6) yes C6 . C7 . N1 . 124.9(5) yes C6 . C7 . H71 . 117.9 no N1 . C7 . H71 . 117.3 no N1 . C8 . C9 . 116.6(4) yes N1 . C8 . C13 . 107.0(3) yes C9 . C8 . C13 . 111.6(4) yes N1 . C8 . H81 . 107.1 no C9 . C8 . H81 . 107.1 no C13 . C8 . H81 . 107.0 no C8 . C9 . C10 . 109.8(5) yes C8 . C9 . H91 . 109.4 no C10 . C9 . H91 . 109.1 no C8 . C9 . H92 . 109.4 no C10 . C9 . H92 . 109.7 no H91 . C9 . H92 . 109.5 no C9 . C10 . C11 . 112.5(4) yes C9 . C10 . H101 . 108.5 no C11 . C10 . H101 . 108.5 no C9 . C10 . H102 . 109.1 no C11 . C10 . H102 . 108.8 no H101 . C10 . H102 . 109.5 no C10 . C11 . C12 . 112.5(4) yes C10 . C11 . H111 . 108.7 no C12 . C11 . H111 . 108.9 no C10 . C11 . H112 . 108.8 no C12 . C11 . H112 . 108.4 no H111 . C11 . H112 . 109.5 no C11 . C12 . C13 . 108.9(4) yes C11 . C12 . H121 . 109.5 no C13 . C12 . H121 . 109.7 no C11 . C12 . H122 . 109.7 no C13 . C12 . H122 . 109.6 no H121 . C12 . H122 . 109.5 no C12 . C13 . C8 . 112.2(3) yes C12 . C13 . N2 . 115.5(3) yes C8 . C13 . N2 . 106.7(3) yes C12 . C13 . H131 . 107.3 no C8 . C13 . H131 . 107.3 no N2 . C13 . H131 . 107.4 no N2 . C14 . C15 . 125.8(5) yes N2 . C14 . H141 . 117.1 no C15 . C14 . H141 . 117.0 no C14 . C15 . C16 . 118.3(6) yes C14 . C15 . C20 . 121.3(6) yes C16 . C15 . C20 . 120.2(5) yes C15 . C16 . C17 . 123.6(6) yes C15 . C16 . H161 . 118.1 no C17 . C16 . H161 . 118.3 no C16 . C17 . C18 . 117.9(6) yes C16 . C17 . H171 . 120.6 no C18 . C17 . H171 . 121.5 no C17 . C18 . C19 . 121.5(5) yes C17 . C18 . H181 . 119.1 no C19 . C18 . H181 . 119.4 no C18 . C19 . C20 . 121.2(5) yes C18 . C19 . O7 . 124.5(5) yes C20 . C19 . O7 . 114.3(5) yes C19 . C20 . C15 . 115.6(5) yes C19 . C20 . O2 . 118.0(5) yes C15 . C20 . O2 . 126.3(5) yes C22 . C21 . O5 . 108.2(4) yes C22 . C21 . H211 . 110.4 no O5 . C21 . H211 . 110.2 no C22 . C21 . H212 . 109.2 no O5 . C21 . H212 . 109.3 no H211 . C21 . H212 . 109.5 no C21 . C22 . H221 . 109.7 no C21 . C22 . H222 . 108.8 no H221 . C22 . H222 . 109.5 no C21 . C22 . H223 . 110.0 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no C24 . C23 . O7 . 106.7(4) yes C24 . C23 . H231 . 110.4 no O7 . C23 . H231 . 110.3 no C24 . C23 . H232 . 109.8 no O7 . C23 . H232 . 110.2 no H231 . C23 . H232 . 109.5 no C23 . C24 . H241 . 109.3 no C23 . C24 . H242 . 109.3 no H241 . C24 . H242 . 109.5 no C23 . C24 . H243 . 109.8 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no C32 . C31 . C36 . 116.8(5) yes C32 . C31 . O3 . 118.4(5) yes C36 . C31 . O3 . 124.8(5) yes C31 . C32 . C33 . 122.3(5) yes C31 . C32 . O6 . 112.6(5) yes C33 . C32 . O6 . 125.1(5) yes C32 . C33 . C34 . 120.5(5) yes C32 . C33 . H331 . 119.7 no C34 . C33 . H331 . 119.9 no C33 . C34 . C35 . 120.1(6) yes C33 . C34 . H341 . 119.5 no C35 . C34 . H341 . 120.4 no C34 . C35 . C36 . 119.5(6) yes C34 . C35 . H351 . 120.4 no C36 . C35 . H351 . 120.1 no C35 . C36 . C31 . 120.7(5) yes C35 . C36 . C37 . 115.5(5) yes C31 . C36 . C37 . 123.7(6) yes C36 . C37 . N3 . 124.9(5) yes C36 . C37 . H371 . 117.5 no N3 . C37 . H371 . 117.7 no N3 . C38 . C39 . 116.1(3) yes N3 . C38 . C43 . 106.9(3) yes C39 . C38 . C43 . 112.3(3) yes N3 . C38 . H381 . 107.1 no C39 . C38 . H381 . 107.0 no C43 . C38 . H381 . 107.0 no C38 . C39 . C40 . 108.9(4) yes C38 . C39 . H391 . 109.6 no C40 . C39 . H391 . 109.8 no C38 . C39 . H392 . 109.5 no C40 . C39 . H392 . 109.6 no H391 . C39 . H392 . 109.5 no C39 . C40 . C41 . 111.0(3) yes C39 . C40 . H401 . 108.9 no C41 . C40 . H401 . 109.2 no C39 . C40 . H402 . 109.2 no C41 . C40 . H402 . 109.0 no H401 . C40 . H402 . 109.5 no C40 . C41 . C42 . 111.9(3) yes C40 . C41 . H411 . 108.7 no C42 . C41 . H411 . 109.0 no C40 . C41 . H412 . 109.0 no C42 . C41 . H412 . 108.8 no H411 . C41 . H412 . 109.5 no C41 . C42 . C43 . 109.6(4) yes C41 . C42 . H421 . 109.6 no C43 . C42 . H421 . 109.8 no C41 . C42 . H422 . 109.5 no C43 . C42 . H422 . 108.9 no H421 . C42 . H422 . 109.5 no C42 . C43 . C38 . 110.6(3) yes C42 . C43 . N4 . 115.8(4) yes C38 . C43 . N4 . 105.5(3) yes C42 . C43 . H431 . 108.4 no C38 . C43 . H431 . 108.1 no N4 . C43 . H431 . 108.2 no N4 . C44 . C45 . 126.8(5) yes N4 . C44 . H441 . 116.8 no C45 . C44 . H441 . 116.3 no C44 . C45 . C46 . 116.9(5) yes C44 . C45 . C50 . 122.1(6) yes C46 . C45 . C50 . 120.9(6) yes C45 . C46 . C47 . 121.7(6) yes C45 . C46 . H461 . 119.2 no C47 . C46 . H461 . 119.1 no C46 . C47 . C48 . 119.3(6) yes C46 . C47 . H471 . 120.3 no C48 . C47 . H471 . 120.4 no C47 . C48 . C49 . 119.7(6) yes C47 . C48 . H481 . 120.1 no C49 . C48 . H481 . 120.3 no C48 . C49 . C50 . 122.7(5) yes C48 . C49 . O8 . 124.2(5) yes C50 . C49 . O8 . 113.0(5) yes C49 . C50 . C45 . 115.7(5) yes C49 . C50 . O4 . 119.1(5) yes C45 . C50 . O4 . 125.2(5) yes C52 . C51 . O6 . 108.7(5) yes C52 . C51 . H511 . 109.4 no O6 . C51 . H511 . 109.6 no C52 . C51 . H512 . 110.0 no O6 . C51 . H512 . 109.7 no H511 . C51 . H512 . 109.5 no C51 . C52 . H521 . 109.7 no C51 . C52 . H522 . 109.7 no H521 . C52 . H522 . 109.5 no C51 . C52 . H523 . 109.0 no H521 . C52 . H523 . 109.5 no H522 . C52 . H523 . 109.5 no C54 . C53 . O8 . 106.1(7) yes C54 . C53 . H531 . 110.0 no O8 . C53 . H531 . 109.9 no C54 . C53 . H532 . 110.8 no O8 . C53 . H532 . 110.4 no H531 . C53 . H532 . 109.5 no C53 . C54 . H541 . 109.2 no C53 . C54 . H542 . 110.0 no H541 . C54 . H542 . 109.5 no C53 . C54 . H543 . 109.2 no H541 . C54 . H543 . 109.5 no H542 . C54 . H543 . 109.5 no C64 . C63 . O8 . 104.3(6) yes C64 . C63 . H631 . 110.7 no O8 . C63 . H631 . 111.0 no C64 . C63 . H632 . 110.5 no O8 . C63 . H632 . 110.9 no H631 . C63 . H632 . 109.5 no C63 . C64 . H641 . 109.6 no C63 . C64 . H642 . 109.3 no H641 . C64 . H642 . 109.5 no C63 . C64 . H643 . 109.5 no H641 . C64 . H643 . 109.5 no H642 . C64 . H643 . 109.5 no C82 . C81 . C90 . 119.5(5) yes C82 . C81 . C91 . 116.6(5) yes C90 . C81 . C91 . 123.8(5) yes C81 . C82 . C83 . 120.7(5) yes C81 . C82 . H821 . 119.7 no C83 . C82 . H821 . 119.6 no C82 . C83 . C84 . 120.3(6) yes C82 . C83 . H831 . 119.8 no C84 . C83 . H831 . 119.9 no C83 . C84 . C85 . 121.9(5) yes C83 . C84 . C89 . 118.9(4) yes C85 . C84 . C89 . 119.2(4) yes C84 . C85 . C86 . 120.5(5) yes C84 . C85 . H851 . 119.8 no C86 . C85 . H851 . 119.7 no C85 . C86 . C87 . 119.4(5) yes C85 . C86 . C92 . 121.3(5) yes C87 . C86 . C92 . 119.3(5) yes C86 . C87 . C88 . 120.8(5) yes C86 . C87 . H871 . 119.5 no C88 . C87 . H871 . 119.8 no C87 . C88 . C89 . 121.8(5) yes C87 . C88 . H881 . 119.1 no C89 . C88 . H881 . 119.1 no C84 . C89 . C88 . 118.2(4) yes C84 . C89 . C90 . 118.5(4) yes C88 . C89 . C90 . 123.2(5) yes C89 . C90 . C81 . 122.0(5) yes C89 . C90 . H901 . 119.1 no C81 . C90 . H901 . 118.9 no C81 . C91 . O13 . 112.5(5) yes C81 . C91 . O14 . 123.7(5) yes O13 . C91 . O14 . 123.8(5) yes C86 . C92 . O11 . 121.1(5) yes C86 . C92 . O12 . 113.7(5) yes O11 . C92 . O12 . 125.2(5) yes C1 . O1 . Cu1 . 127.2(3) yes C20 . O2 . Cu1 . 125.9(3) yes C31 . O3 . Cu2 . 125.3(3) yes C50 . O4 . Cu2 . 126.7(3) yes C21 . O5 . C2 . 116.8(4) yes C51 . O6 . C32 . 117.2(4) yes C23 . O7 . C19 . 116.0(4) yes C53 . O8 . C49 . 107.5(5) yes C63 . O8 . C49 . 124.9(5) yes C92 . O12 . H1 . 112.3 no C91 . O13 . H2 . 116.2 no H3 . O51 . H4 . 106.0 no H5 . O52 . H6 . 105.5 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 O12 . H1 . O52 . 159 0.82 1.80 2.581(2) yes O13 . H2 . O51 . 174 0.82 1.77 2.587(2) yes O51 . H3 . O4 . 148 0.82 2.19 2.915(2) yes O51 . H3 . O8 . 139 0.82 2.17 2.835(2) yes O51 . H4 . O6 . 148 0.82 2.17 2.897(2) yes O52 . H5 . O5 . 147 0.82 2.20 2.923(2) yes # Attachment 'gq19_123.cif' data_gq19_123k _database_code_depnum_ccdc_archive 'CCDC 704885' _audit_creation_date 08-08-28 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'gq19_123k_0m in P2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.5583(2) _cell_length_b 20.5367(6) _cell_length_c 10.8240(3) _cell_angle_alpha 90 _cell_angle_beta 103.4820(10) _cell_angle_gamma 90 _cell_volume 1201.50(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C24 H30 Cu1 N2 O4 # Dc = 1.68 Fooo = 558.00 Mu = 24.66 M = 608.89 # Found Formula = C26 H33 Cu1 N3 O5 # Dc = 1.47 FOOO = 558.00 Mu = 9.52 M = 531.11 _chemical_formula_sum 'C26 H33 Cu1 N3 O5' _chemical_formula_moiety 'C24 H30 Cu N2 O5, C2 H3 N' _chemical_compound_source ? _chemical_formula_weight 531.11 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 123 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.27 _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 558 _exptl_absorpt_coefficient_mu 0.952 # Sheldrick geometric approximatio 0.80 0.93 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.93 # 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_type 'Nonius KappaCCD' _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 64485 _reflns_number_total 8825 _diffrn_reflns_av_R_equivalents 0.036 # Number of reflections with Friedels Law is 4530 # Number of reflections without Friedels Law is 8825 # Theoretical number of reflections is about 4417 _diffrn_reflns_theta_min 1.935 _diffrn_reflns_theta_max 32.697 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 32.697 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min -31 _reflns_limit_k_max 31 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _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 -0.96 _refine_diff_density_max 0.93 _refine_ls_number_reflns 6684 _refine_ls_number_restraints 4 _refine_ls_number_parameters 317 #_refine_ls_R_factor_ref 0.0227 _refine_ls_wR_factor_ref 0.0240 _refine_ls_goodness_of_fit_ref 1.0850 #_reflns_number_all 8813 _refine_ls_R_factor_all 0.0328 _refine_ls_wR_factor_all 0.0273 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 6684 _refine_ls_R_factor_gt 0.0227 _refine_ls_wR_factor_gt 0.0240 _refine_ls_shift/su_max 0.000392 _refine_ls_abs_structure_Flack 0.011(6) _refine_ls_abs_structure_details 'Flack (1983), 4295 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: 1.04 0.498 1.09 0.166 0.245 ; _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_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 Fih. ; ? ; _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. ; _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 ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. 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 _atom_site_attached_hydrogens Cu2 Cu 0.55406(3) 0.43659(4) 0.551823(13) 0.0121 1.0000 Uani . . . . . . N1 N 0.46457(19) 0.44388(8) 0.71684(10) 0.0137 1.0000 Uani . . . . . . N2 N 0.3369(2) 0.51219(7) 0.50663(10) 0.0127 1.0000 Uani . . . . . . N3 N 0.4531(4) 0.19887(9) 0.16145(17) 0.0404 1.0000 Uani . . . . . . O1 O 0.78873(19) 0.36852(6) 0.61131(9) 0.0160 1.0000 Uani . . . . . . O2 O 0.68961(17) 0.44535(6) 0.40342(8) 0.0148 1.0000 Uani . . . . . . O3 O 1.1002(2) 0.27260(6) 0.64134(11) 0.0193 1.0000 Uani . . . . . . O4 O 0.92445(16) 0.43876(9) 0.22138(8) 0.0188 1.0000 Uani . . . . . . O5 O 0.1892(2) 0.37232(6) 0.46228(10) 0.0188 1.0000 Uani D U . . . . C1 C 0.8062(2) 0.33412(7) 0.71443(12) 0.0142 1.0000 Uani . . . . . . C2 C 0.9766(3) 0.28048(8) 0.73521(14) 0.0157 1.0000 Uani . . . . . . C3 C 1.0042(3) 0.24078(8) 0.84117(14) 0.0191 1.0000 Uani . . . . . . C4 C 0.8630(3) 0.25194(8) 0.93151(14) 0.0211 1.0000 Uani . . . . . . C5 C 0.7006(3) 0.30324(8) 0.91542(13) 0.0193 1.0000 Uani . . . . . . C6 C 0.6719(3) 0.34531(7) 0.80880(12) 0.0154 1.0000 Uani . . . . . . C7 C 0.5130(3) 0.40099(8) 0.80572(12) 0.0158 1.0000 Uani . . . . . . C8 C 0.3259(2) 0.50390(7) 0.72852(12) 0.0133 1.0000 Uani . . . . . . C9 C 0.1615(3) 0.50308(8) 0.82356(13) 0.0184 1.0000 Uani . . . . . . C10 C 0.0414(3) 0.57010(8) 0.82410(14) 0.0211 1.0000 Uani . . . . . . C11 C -0.1024(3) 0.59019(9) 0.69238(15) 0.0215 1.0000 Uani . . . . . . C12 C 0.0567(3) 0.58803(8) 0.59455(15) 0.0182 1.0000 Uani . . . . . . C13 C 0.1741(2) 0.52094(7) 0.59495(12) 0.0135 1.0000 Uani . . . . . . C14 C 0.3167(2) 0.54769(7) 0.40717(12) 0.0139 1.0000 Uani . . . . . . C15 C 0.4603(2) 0.54111(7) 0.31320(12) 0.0135 1.0000 Uani . . . . . . C16 C 0.6356(2) 0.49045(7) 0.31658(12) 0.0130 1.0000 Uani . . . . . . C17 C 0.7608(3) 0.48905(8) 0.21468(12) 0.0154 1.0000 Uani . . . . . . C18 C 0.7143(3) 0.53546(8) 0.11942(12) 0.0188 1.0000 Uani . . . . . . C19 C 0.5399(3) 0.58515(8) 0.11844(13) 0.0188 1.0000 Uani . . . . . . C20 C 0.4144(3) 0.58753(8) 0.21336(13) 0.0169 1.0000 Uani . . . . . . C21 C 1.2725(3) 0.21985(8) 0.65471(14) 0.0193 1.0000 Uani . . . . . . C22 C 1.3879(3) 0.22160(8) 0.54189(15) 0.0228 1.0000 Uani . . . . . . C23 C 1.0500(2) 0.43362(12) 0.11987(11) 0.0188 1.0000 Uani . . . . . . C24 C 1.2227(3) 0.37636(9) 0.14867(16) 0.0246 1.0000 Uani . . . . . . C25 C 0.5767(3) 0.23481(9) 0.22724(17) 0.0284 1.0000 Uani . . . . . . C26 C 0.7364(5) 0.28021(11) 0.3115(2) 0.0449 1.0000 Uani . . . . . . H1 H 0.0632 0.3868 0.4122 0.0305 1.0000 Uiso DR U . . . . H2 H 0.1132 0.3552 0.5120 0.0304 1.0000 Uiso DR U . . . . H31 H 1.1156 0.2073 0.8517 0.0229 1.0000 Uiso R . . . . . H41 H 0.8814 0.2241 1.0001 0.0253 1.0000 Uiso R . . . . . H51 H 0.6062 0.3100 0.9757 0.0236 1.0000 Uiso R . . . . . H71 H 0.4405 0.4062 0.8745 0.0194 1.0000 Uiso R . . . . . H81 H 0.4506 0.5384 0.7535 0.0170 1.0000 Uiso R . . . . . H91 H 0.2578 0.4937 0.9083 0.0239 1.0000 Uiso R . . . . . H92 H 0.0393 0.4689 0.8015 0.0232 1.0000 Uiso R . . . . . H101 H 0.1691 0.6020 0.8539 0.0275 1.0000 Uiso R . . . . . H102 H -0.0720 0.5696 0.8799 0.0268 1.0000 Uiso R . . . . . H111 H -0.1694 0.6333 0.6951 0.0270 1.0000 Uiso R . . . . . H112 H -0.2347 0.5599 0.6658 0.0271 1.0000 Uiso R . . . . . H121 H 0.1827 0.6206 0.6138 0.0228 1.0000 Uiso R . . . . . H122 H -0.0422 0.5970 0.5123 0.0223 1.0000 Uiso R . . . . . H131 H 0.0386 0.4912 0.5752 0.0208 1.0000 Uiso R . . . . . H141 H 0.1974 0.5808 0.3937 0.0167 1.0000 Uiso R . . . . . H181 H 0.8013 0.5339 0.0569 0.0228 1.0000 Uiso R . . . . . H191 H 0.5129 0.6154 0.0529 0.0214 1.0000 Uiso R . . . . . H201 H 0.2991 0.6201 0.2133 0.0197 1.0000 Uiso R . . . . . H211 H 1.3976 0.2263 0.7316 0.0232 1.0000 Uiso R . . . . . H212 H 1.1870 0.1793 0.6572 0.0227 1.0000 Uiso R . . . . . H221 H 1.5046 0.1867 0.5489 0.0352 1.0000 Uiso R . . . . . H222 H 1.4689 0.2624 0.5374 0.0350 1.0000 Uiso R . . . . . H223 H 1.2608 0.2163 0.4655 0.0348 1.0000 Uiso R . . . . . H231 H 1.1398 0.4725 0.1155 0.0235 1.0000 Uiso R . . . . . H232 H 0.9301 0.4282 0.0408 0.0236 1.0000 Uiso R . . . . . H241 H 1.3179 0.3724 0.0843 0.0388 1.0000 Uiso R . . . . . H242 H 1.3347 0.3814 0.2311 0.0389 1.0000 Uiso R . . . . . H243 H 1.1305 0.3374 0.1477 0.0392 1.0000 Uiso R . . . . . H261 H 0.6491 0.3188 0.3192 0.0653 1.0000 Uiso R . . . . . H262 H 0.8767 0.2900 0.2792 0.0654 1.0000 Uiso R . . . . . H263 H 0.7902 0.2607 0.3932 0.0645 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 Cu2 0.01400(6) 0.01333(6) 0.00953(5) 0.00222(8) 0.00417(4) 0.00177(8) N1 0.0145(4) 0.0146(6) 0.0125(4) 0.0013(4) 0.0040(3) 0.0002(4) N2 0.0142(5) 0.0141(5) 0.0107(4) -0.0003(4) 0.0043(4) -0.0009(4) N3 0.0475(10) 0.0336(8) 0.0388(9) -0.0011(7) 0.0071(8) -0.0057(7) O1 0.0177(4) 0.0170(4) 0.0144(4) 0.0051(3) 0.0059(3) 0.0051(4) O2 0.0170(4) 0.0165(6) 0.0113(3) 0.0036(3) 0.0045(3) 0.0025(4) O3 0.0217(5) 0.0184(5) 0.0191(5) 0.0046(4) 0.0075(4) 0.0072(4) O4 0.0211(4) 0.0235(4) 0.0143(3) 0.0037(6) 0.0095(3) 0.0049(6) O5 0.0183(5) 0.0197(5) 0.0180(4) 0.0025(4) 0.0034(4) -0.0012(4) C1 0.0151(5) 0.0150(5) 0.0120(5) 0.0022(4) 0.0020(4) -0.0002(4) C2 0.0163(6) 0.0150(6) 0.0152(6) 0.0024(5) 0.0024(5) 0.0024(5) C3 0.0224(6) 0.0153(6) 0.0184(6) 0.0048(5) 0.0024(5) 0.0030(5) C4 0.0280(7) 0.0189(6) 0.0154(6) 0.0062(5) 0.0027(5) 0.0012(5) C5 0.0256(7) 0.0205(6) 0.0127(5) 0.0050(5) 0.0062(5) 0.0012(5) C6 0.0187(6) 0.0157(6) 0.0117(5) 0.0026(4) 0.0036(4) -0.0009(5) C7 0.0180(6) 0.0183(6) 0.0118(5) 0.0019(4) 0.0049(4) 0.0004(5) C8 0.0132(5) 0.0161(5) 0.0112(5) 0.0005(4) 0.0043(4) 0.0004(4) C9 0.0209(6) 0.0211(6) 0.0159(6) 0.0029(5) 0.0100(5) 0.0027(5) C10 0.0253(7) 0.0242(7) 0.0169(6) 0.0006(5) 0.0114(5) 0.0052(5) C11 0.0181(7) 0.0270(7) 0.0219(7) 0.0011(6) 0.0098(5) 0.0077(6) C12 0.0216(7) 0.0196(7) 0.0158(6) 0.0022(5) 0.0090(5) 0.0054(5) C13 0.0128(5) 0.0160(5) 0.0123(5) 0.0009(4) 0.0043(4) 0.0001(4) C14 0.0147(5) 0.0143(5) 0.0124(5) -0.0002(4) 0.0026(4) 0.0001(4) C15 0.0162(5) 0.0137(5) 0.0101(5) 0.0002(4) 0.0023(4) -0.0011(4) C16 0.0144(5) 0.0153(5) 0.0092(5) 0.0015(4) 0.0025(4) -0.0015(4) C17 0.0169(6) 0.0175(6) 0.0123(5) 0.0014(4) 0.0044(4) -0.0003(4) C18 0.0236(7) 0.0225(6) 0.0113(5) 0.0033(5) 0.0061(5) -0.0030(5) C19 0.0243(6) 0.0188(6) 0.0125(5) 0.0051(5) 0.0030(5) -0.0020(5) C20 0.0209(6) 0.0144(6) 0.0149(6) 0.0016(4) 0.0028(5) -0.0005(5) C21 0.0203(6) 0.0148(6) 0.0219(6) 0.0006(5) 0.0032(5) 0.0038(5) C22 0.0244(7) 0.0210(7) 0.0238(7) -0.0017(5) 0.0072(5) 0.0039(5) C23 0.0205(5) 0.0250(6) 0.0130(4) -0.0021(7) 0.0084(4) -0.0013(8) C24 0.0256(7) 0.0259(7) 0.0251(7) -0.0053(6) 0.0118(6) 0.0020(6) C25 0.0311(8) 0.0254(8) 0.0292(8) 0.0063(6) 0.0078(6) 0.0020(6) C26 0.0472(12) 0.0360(10) 0.0442(11) 0.0027(9) -0.0039(9) -0.0111(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.5070(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu2 . N1 . 1.9683(10) yes Cu2 . N2 . 1.9572(12) yes Cu2 . O1 . 1.9180(10) yes Cu2 . O2 . 1.9351(9) yes Cu2 . O5 . 2.4245(10) yes N1 . C7 . 1.2856(18) yes N1 . C8 . 1.4748(18) yes N2 . C13 . 1.4728(16) yes N2 . C14 . 1.2832(17) yes N3 . C25 . 1.138(3) yes O1 . C1 . 1.3053(16) yes O2 . C16 . 1.3039(16) yes O3 . C2 . 1.3624(18) yes O3 . C21 . 1.4310(17) yes O4 . C17 . 1.3671(19) yes O4 . C23 . 1.4364(13) yes O5 . H1 . 0.834 no O5 . H2 . 0.835 no C1 . C2 . 1.4357(19) yes C1 . C6 . 1.4175(19) yes C2 . C3 . 1.3862(18) yes C3 . C4 . 1.408(2) yes C3 . H31 . 0.915 no C4 . C5 . 1.372(2) yes C4 . H41 . 0.923 no C5 . C6 . 1.4205(19) yes C5 . H51 . 0.938 no C6 . C7 . 1.4404(19) yes C7 . H71 . 0.932 no C8 . C9 . 1.5269(18) yes C8 . C13 . 1.5350(18) yes C8 . H81 . 0.984 no C9 . C10 . 1.530(2) yes C9 . H91 . 0.967 no C9 . H92 . 0.967 no C10 . C11 . 1.520(2) yes C10 . H101 . 0.964 no C10 . H102 . 0.969 no C11 . C12 . 1.530(2) yes C11 . H111 . 0.963 no C11 . H112 . 0.955 no C12 . C13 . 1.524(2) yes C12 . H121 . 0.955 no C12 . H122 . 0.949 no C13 . H131 . 0.954 no C14 . C15 . 1.4381(18) yes C14 . H141 . 0.938 no C15 . C16 . 1.4201(19) yes C15 . C20 . 1.4189(18) yes C16 . C17 . 1.4350(18) yes C17 . C18 . 1.3834(18) yes C18 . C19 . 1.406(2) yes C18 . H181 . 0.920 no C19 . C20 . 1.371(2) yes C19 . H191 . 0.928 no C20 . H201 . 0.926 no C21 . C22 . 1.506(2) yes C21 . H211 . 0.961 no C21 . H212 . 0.962 no C22 . H221 . 0.958 no C22 . H222 . 0.958 no C22 . H223 . 0.960 no C23 . C24 . 1.504(3) yes C23 . H231 . 0.949 no C23 . H232 . 0.961 no C24 . H241 . 0.972 no C24 . H242 . 0.967 no C24 . H243 . 0.948 no C25 . C26 . 1.453(3) yes C26 . H261 . 0.944 no C26 . H262 . 0.948 no C26 . H263 . 0.953 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 . Cu2 . N2 . 83.97(5) yes N1 . Cu2 . O1 . 92.68(5) yes N2 . Cu2 . O1 . 173.47(5) yes N1 . Cu2 . O2 . 167.39(5) yes N2 . Cu2 . O2 . 93.19(4) yes O1 . Cu2 . O2 . 88.88(4) yes N1 . Cu2 . O5 . 92.25(4) yes N2 . Cu2 . O5 . 85.55(4) yes O1 . Cu2 . O5 . 100.21(4) yes O2 . Cu2 . O5 . 99.79(4) yes Cu2 . N1 . C7 . 125.01(10) yes Cu2 . N1 . C8 . 112.89(8) yes C7 . N1 . C8 . 122.07(11) yes Cu2 . N2 . C13 . 111.78(8) yes Cu2 . N2 . C14 . 126.06(10) yes C13 . N2 . C14 . 121.89(12) yes Cu2 . O1 . C1 . 126.21(9) yes Cu2 . O2 . C16 . 126.55(9) yes C2 . O3 . C21 . 117.17(12) yes C17 . O4 . C23 . 116.81(13) yes Cu2 . O5 . H1 . 124.2 no Cu2 . O5 . H2 . 118.3 no H1 . O5 . H2 . 95.5 no O1 . C1 . C2 . 117.66(12) yes O1 . C1 . C6 . 125.58(12) yes C2 . C1 . C6 . 116.77(12) yes C1 . C2 . O3 . 113.77(12) yes C1 . C2 . C3 . 121.51(13) yes O3 . C2 . C3 . 124.70(13) yes C2 . C3 . C4 . 120.45(13) yes C2 . C3 . H31 . 119.1 no C4 . C3 . H31 . 120.4 no C3 . C4 . C5 . 119.58(13) yes C3 . C4 . H41 . 118.9 no C5 . C4 . H41 . 121.6 no C4 . C5 . C6 . 121.08(14) yes C4 . C5 . H51 . 118.9 no C6 . C5 . H51 . 120.0 no C5 . C6 . C1 . 120.57(13) yes C5 . C6 . C7 . 116.99(12) yes C1 . C6 . C7 . 122.34(12) yes C6 . C7 . N1 . 125.56(13) yes C6 . C7 . H71 . 116.7 no N1 . C7 . H71 . 117.7 no N1 . C8 . C9 . 117.08(11) yes N1 . C8 . C13 . 107.06(10) yes C9 . C8 . C13 . 110.67(11) yes N1 . C8 . H81 . 106.1 no C9 . C8 . H81 . 108.5 no C13 . C8 . H81 . 107.0 no C8 . C9 . C10 . 108.83(11) yes C8 . C9 . H91 . 110.8 no C10 . C9 . H91 . 108.7 no C8 . C9 . H92 . 109.7 no C10 . C9 . H92 . 111.8 no H91 . C9 . H92 . 107.0 no C9 . C10 . C11 . 112.03(12) yes C9 . C10 . H101 . 108.9 no C11 . C10 . H101 . 108.3 no C9 . C10 . H102 . 109.9 no C11 . C10 . H102 . 108.1 no H101 . C10 . H102 . 109.5 no C10 . C11 . C12 . 112.26(12) yes C10 . C11 . H111 . 110.1 no C12 . C11 . H111 . 109.8 no C10 . C11 . H112 . 107.8 no C12 . C11 . H112 . 107.5 no H111 . C11 . H112 . 109.4 no C11 . C12 . C13 . 109.91(12) yes C11 . C12 . H121 . 110.0 no C13 . C12 . H121 . 109.9 no C11 . C12 . H122 . 110.0 no C13 . C12 . H122 . 109.4 no H121 . C12 . H122 . 107.7 no C8 . C13 . C12 . 110.48(11) yes C8 . C13 . N2 . 107.30(10) yes C12 . C13 . N2 . 115.85(11) yes C8 . C13 . H131 . 107.3 no C12 . C13 . H131 . 105.2 no N2 . C13 . H131 . 110.4 no N2 . C14 . C15 . 125.83(13) yes N2 . C14 . H141 . 117.6 no C15 . C14 . H141 . 116.5 no C14 . C15 . C16 . 122.77(12) yes C14 . C15 . C20 . 116.41(12) yes C16 . C15 . C20 . 120.80(12) yes C15 . C16 . O2 . 125.47(12) yes C15 . C16 . C17 . 116.60(11) yes O2 . C16 . C17 . 117.93(12) yes C16 . C17 . O4 . 114.22(11) yes C16 . C17 . C18 . 121.27(13) yes O4 . C17 . C18 . 124.50(12) yes C17 . C18 . C19 . 120.96(13) yes C17 . C18 . H181 . 119.0 no C19 . C18 . H181 . 120.0 no C18 . C19 . C20 . 119.38(13) yes C18 . C19 . H191 . 118.7 no C20 . C19 . H191 . 121.9 no C15 . C20 . C19 . 120.97(13) yes C15 . C20 . H201 . 119.2 no C19 . C20 . H201 . 119.9 no O3 . C21 . C22 . 107.54(12) yes O3 . C21 . H211 . 108.4 no C22 . C21 . H211 . 109.9 no O3 . C21 . H212 . 109.5 no C22 . C21 . H212 . 110.5 no H211 . C21 . H212 . 110.9 no C21 . C22 . H221 . 109.0 no C21 . C22 . H222 . 110.8 no H221 . C22 . H222 . 110.0 no C21 . C22 . H223 . 109.2 no H221 . C22 . H223 . 109.4 no H222 . C22 . H223 . 108.4 no O4 . C23 . C24 . 107.41(14) yes O4 . C23 . H231 . 109.4 no C24 . C23 . H231 . 110.6 no O4 . C23 . H232 . 109.2 no C24 . C23 . H232 . 111.8 no H231 . C23 . H232 . 108.4 no C23 . C24 . H241 . 110.2 no C23 . C24 . H242 . 110.5 no H241 . C24 . H242 . 109.3 no C23 . C24 . H243 . 109.9 no H241 . C24 . H243 . 107.7 no H242 . C24 . H243 . 109.2 no N3 . C25 . C26 . 179.4(2) yes C25 . C26 . H261 . 110.1 no C25 . C26 . H262 . 109.9 no H261 . C26 . H262 . 109.7 no C25 . C26 . H263 . 109.0 no H261 . C26 . H263 . 109.2 no H262 . C26 . H263 . 109.0 no # Attachment 'gq26.cif' data_gq26_123k _database_code_depnum_ccdc_archive 'CCDC 704886' _audit_creation_date 08-09-23 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'gq26_123k_0m in P1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.8855(4) _cell_length_b 10.8153(4) _cell_length_c 13.0636(5) _cell_angle_alpha 97.313(2) _cell_angle_beta 109.121(2) _cell_angle_gamma 107.198(2) _cell_volume 1097.61(8) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P 1 ' _symmetry_space_group_name_Hall 'P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,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 2 # Given Formula = C26 H30 Cu1 N2 O8 # Dc = 1.70 Fooo = 514.00 Mu = 10.56 M = 1124.16 # Found Formula = C24 H30 Cu1 N2 O5 # Dc = 1.48 FOOO = 514.00 Mu = 10.34 M = 980.12 _chemical_formula_sum 'C24 H30 Cu1 N2 O5' _chemical_formula_moiety 'C24 H28 Cu N2 O4, H2 O' _chemical_compound_source ? _chemical_formula_weight 490.06 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 123 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_max 0.34 _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 514 _exptl_absorpt_coefficient_mu 1.034 # Sheldrick geometric approximatio 0.87 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.92 # 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_type 'Nonius KappaCCD' _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 39940 _reflns_number_total 18296 _diffrn_reflns_av_R_equivalents 0.033 # Number of reflections with Friedels Law is 9427 # Number of reflections without Friedels Law is 18296 # Theoretical number of reflections is about 9620 _diffrn_reflns_theta_min 1.703 _diffrn_reflns_theta_max 34.974 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 30.428 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -14 _reflns_limit_h_max 14 _reflns_limit_k_min -17 _reflns_limit_k_max 17 _reflns_limit_l_min -21 _reflns_limit_l_max 21 _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 -0.42 _refine_diff_density_max 0.47 _refine_ls_number_reflns 11280 _refine_ls_number_restraints 59 _refine_ls_number_parameters 578 #_refine_ls_R_factor_ref 0.0311 _refine_ls_wR_factor_ref 0.0317 _refine_ls_goodness_of_fit_ref 1.0829 #_reflns_number_all 18264 _refine_ls_R_factor_all 0.0652 _refine_ls_wR_factor_all 0.0561 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 11280 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_gt 0.0317 _refine_ls_shift/su_max 0.022230 _refine_ls_abs_structure_Flack 0.011(10) _refine_ls_abs_structure_details 'Flack (1983), 8869 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 noref # 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: 0.431 0.201 0.244 ; # start Validation Reply Form _vrf_PLAT113_gq26_123k ; PROBLEM: ADDSYM Suggests Possible Pseudo/New Space-group. P-1 RESPONSE: gq26_123k is enantiomerically pure. The ligands of the two complexes have (R,R) configuration both. The Flack parameter was refined unequivocally (0.006(10)) ; _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_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 Fih. ; ? ; _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. ; _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 ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., 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. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. 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 _atom_site_attached_hydrogens Cu1 Cu 0.06558(9) 0.49361(7) 0.30181(7) 0.0129 1.0000 Uani . . . . . . N1 N -0.0723(4) 0.4691(3) 0.1460(3) 0.0140 1.0000 Uani . . . . . . N2 N 0.0916(4) 0.3271(3) 0.2479(3) 0.0157 1.0000 Uani . . . . . . C1 C -0.0526(5) 0.7147(4) 0.2823(4) 0.0135 1.0000 Uani . . . . . . C2 C -0.0408(5) 0.8445(5) 0.3307(4) 0.0171 1.0000 Uani . . . . . . C3 C -0.1397(6) 0.9096(4) 0.2692(4) 0.0167 1.0000 Uani . . . . . . C4 C -0.2605(6) 0.8422(5) 0.1604(4) 0.0211 1.0000 Uani . . . . . . C5 C -0.2741(5) 0.7162(4) 0.1130(4) 0.0171 1.0000 Uani . . . . . . C6 C -0.1674(6) 0.6525(5) 0.1712(4) 0.0167 1.0000 Uani . . . . . . C7 C -0.1680(5) 0.5342(4) 0.1081(4) 0.0147 1.0000 Uani . . . . . . C8 C -0.0543(3) 0.3656(2) 0.07030(19) 0.0162 1.0000 Uani . . . . . . C9 C -0.1936(7) 0.3061(5) -0.0459(5) 0.0231 1.0000 Uani . . . . . . C10 C -0.1526(5) 0.2028(3) -0.1119(2) 0.0299 1.0000 Uani . . . . . . C11 C -0.1252(4) 0.0959(3) -0.0503(2) 0.0286 1.0000 Uani . . . . . . C12 C 0.0118(6) 0.1548(5) 0.0677(4) 0.0236 1.0000 Uani . . . . . . C13 C -0.0319(3) 0.2576(2) 0.13260(19) 0.0166 1.0000 Uani . . . . . . C14 C 0.2061(6) 0.2821(4) 0.3038(4) 0.0196 1.0000 Uani . . . . . . C15 C 0.3147(6) 0.3358(5) 0.4176(5) 0.0187 1.0000 Uani . U . . . . C16 C 0.4320(6) 0.2716(5) 0.4654(5) 0.0245 1.0000 Uani . U . . . . C17 C 0.5337(6) 0.3107(5) 0.5744(5) 0.0233 1.0000 Uani . U . . . . C18 C 0.5250(6) 0.4172(5) 0.6450(5) 0.0245 1.0000 Uani . U . . . . C19 C 0.4163(6) 0.4835(5) 0.6034(5) 0.0182 1.0000 Uani . . . . . . C20 C 0.3057(6) 0.4453(5) 0.4859(4) 0.0170 1.0000 Uani . . . . . . C21 C 0.0845(6) 1.0271(4) 0.4966(4) 0.0177 1.0000 Uani . U . . . . C22 C 0.2000(7) 1.0510(5) 0.6176(5) 0.0269 1.0000 Uani . U . . . . C23 C 0.5093(6) 0.6362(5) 0.7800(4) 0.0256 1.0000 Uani . . . . . . C24 C 0.4724(7) 0.7534(5) 0.8262(5) 0.0275 1.0000 Uani . . . . . . O1 O 0.0474(4) 0.6621(3) 0.3466(3) 0.0145 1.0000 Uani . . . . . . O2 O 0.2093(4) 0.5129(3) 0.4532(3) 0.0190 1.0000 Uani . . . . . . O3 O 0.0711(4) 0.8975(3) 0.4401(3) 0.0194 1.0000 Uani . . . . . . O4 O 0.4002(4) 0.5874(4) 0.6626(3) 0.0195 1.0000 Uani . U . . . . O51 O 0.4092(5) 0.3870(4) -0.0668(3) 0.0305 1.0000 Uani . . . . . . Cu2 Cu 0.45049(9) 0.58872(7) 0.21889(7) 0.0136 1.0000 Uani . . . . . . N3 N 0.6186(4) 0.6295(3) 0.3698(3) 0.0155 1.0000 Uani . . . . . . N4 N 0.3938(4) 0.7343(3) 0.2797(3) 0.0162 1.0000 Uani . . . . . . C31 C 0.5641(5) 0.3678(4) 0.2342(3) 0.0137 1.0000 Uani . . . . . . C32 C 0.5502(5) 0.2339(4) 0.1884(4) 0.0132 1.0000 Uani . . . . . . C33 C 0.6432(6) 0.1701(5) 0.2479(4) 0.0205 1.0000 Uani . . . . . . C34 C 0.7662(6) 0.2333(5) 0.3565(4) 0.0224 1.0000 Uani . . . . . . C35 C 0.7884(6) 0.3610(5) 0.4041(4) 0.0221 1.0000 Uani . . . . . . C36 C 0.6866(5) 0.4286(4) 0.3459(4) 0.0134 1.0000 Uani . . . . . . C37 C 0.7071(5) 0.5573(4) 0.4067(4) 0.0155 1.0000 Uani . . . . . . C38 C 0.6433(3) 0.7594(2) 0.43826(18) 0.0156 1.0000 Uani . . . . . . C39 C 0.7260(6) 0.7804(5) 0.5650(4) 0.0212 1.0000 Uani . . . . . . C40 C 0.7364(4) 0.9168(3) 0.6244(2) 0.0254 1.0000 Uani . . . . . . C41 C 0.5642(4) 0.9340(3) 0.5856(2) 0.0254 1.0000 Uani . . . . . . C42 C 0.4848(6) 0.9119(4) 0.4591(4) 0.0208 1.0000 Uani . . . . . . C43 C 0.4700(3) 0.7745(2) 0.40301(18) 0.0161 1.0000 Uani . . . . . . C44 C 0.2948(6) 0.7868(4) 0.2235(4) 0.0176 1.0000 Uani . . . . . . C45 C 0.2025(5) 0.7463(4) 0.1018(4) 0.0158 1.0000 Uani . U . . . . C46 C 0.0911(6) 0.8113(5) 0.0562(4) 0.0209 1.0000 Uani . U . . . . C47 C -0.0036(6) 0.7753(5) -0.0585(5) 0.0280 1.0000 Uani . U . . . . C48 C 0.0082(6) 0.6738(5) -0.1289(5) 0.0242 1.0000 Uani . U . . . . C49 C 0.1162(6) 0.6087(5) -0.0835(4) 0.0184 1.0000 Uani . . . . . . C50 C 0.2150(5) 0.6419(4) 0.0323(4) 0.0157 1.0000 Uani . . . . . . C51 C 0.4232(6) 0.0608(4) 0.0200(4) 0.0200 1.0000 Uani . . . . . . C52 C 0.3128(6) 0.0390(5) -0.1001(4) 0.0279 1.0000 Uani . . . . . . C53 C 0.0285(6) 0.4573(5) -0.2614(5) 0.0244 1.0000 Uani . . . . . . C54 C 0.0671(7) 0.3407(6) -0.3074(5) 0.0272 1.0000 Uani . . . . . . O5 O 0.4674(4) 0.4208(3) 0.1738(3) 0.0178 1.0000 Uani . . . . . . O6 O 0.3121(4) 0.5726(3) 0.0691(3) 0.0161 1.0000 Uani . . . . . . O7 O 0.4360(4) 0.1846(3) 0.0798(3) 0.0213 1.0000 Uani . . . . . . O8 O 0.1372(4) 0.5058(4) -0.1458(3) 0.0218 1.0000 Uani . . . . . . O52 O 0.1274(5) 0.7068(4) 0.5897(3) 0.0281 1.0000 Uani . . . . . . H1 H 0.3594 0.4391 -0.0624 0.0407 1.0000 Uiso . . . . . . H2 H 0.4330 0.3614 -0.0092 0.0407 1.0000 Uiso . . . . . . H3 H 0.0877 0.7227 0.5288 0.0357 1.0000 Uiso . . . . . . H4 H 0.1678 0.6488 0.5826 0.0357 1.0000 Uiso . . . . . . H31 H -0.1253 0.9993 0.3013 0.0216 1.0000 Uiso . . . . . . H41 H -0.3335 0.8843 0.1193 0.0256 1.0000 Uiso . . . . . . H51 H -0.3576 0.6704 0.0389 0.0234 1.0000 Uiso . . . . . . H71 H -0.2462 0.5015 0.0313 0.0184 1.0000 Uiso . . . . . . H81 H 0.0506 0.4058 0.0608 0.0196 1.0000 Uiso . . . . . . H91 H -0.2009 0.3759 -0.0839 0.0270 1.0000 Uiso . . . . . . H92 H -0.3010 0.2640 -0.0402 0.0270 1.0000 Uiso . . . . . . H101 H -0.2456 0.1610 -0.1832 0.0360 1.0000 Uiso . . . . . . H102 H -0.0505 0.2473 -0.1231 0.0360 1.0000 Uiso . . . . . . H111 H -0.2308 0.0459 -0.0458 0.0319 1.0000 Uiso . . . . . . H112 H -0.0911 0.0373 -0.0919 0.0319 1.0000 Uiso . . . . . . H121 H 0.1201 0.1974 0.0635 0.0291 1.0000 Uiso . . . . . . H122 H 0.0170 0.0847 0.1052 0.0291 1.0000 Uiso . . . . . . H131 H -0.1395 0.2117 0.1366 0.0197 1.0000 Uiso . . . . . . H141 H 0.2166 0.2060 0.2643 0.0258 1.0000 Uiso . . . . . . H161 H 0.4375 0.1987 0.4187 0.0310 1.0000 Uiso . . . . . . H171 H 0.6123 0.2674 0.6047 0.0333 1.0000 Uiso . . . . . . H181 H 0.5963 0.4437 0.7230 0.0287 1.0000 Uiso . . . . . . H211 H -0.0260 1.0270 0.4910 0.0220 1.0000 Uiso . . . . . . H212 H 0.1340 1.0952 0.4643 0.0220 1.0000 Uiso . . . . . . H221 H 0.2136 1.1362 0.6590 0.0297 1.0000 Uiso . . . . . . H222 H 0.1497 0.9819 0.6486 0.0297 1.0000 Uiso . . . . . . H223 H 0.3097 1.0501 0.6219 0.0297 1.0000 Uiso . . . . . . H231 H 0.6270 0.6639 0.7888 0.0264 1.0000 Uiso . . . . . . H232 H 0.4858 0.5676 0.8185 0.0264 1.0000 Uiso . . . . . . H241 H 0.5435 0.7892 0.9043 0.0302 1.0000 Uiso . . . . . . H242 H 0.4960 0.8214 0.7867 0.0302 1.0000 Uiso . . . . . . H243 H 0.3548 0.7252 0.8165 0.0302 1.0000 Uiso . . . . . . H331 H 0.6248 0.0793 0.2156 0.0262 1.0000 Uiso . . . . . . H341 H 0.8340 0.1878 0.3970 0.0300 1.0000 Uiso . . . . . . H351 H 0.8736 0.4054 0.4778 0.0245 1.0000 Uiso . . . . . . H371 H 0.7941 0.5930 0.4807 0.0169 1.0000 Uiso . . . . . . H381 H 0.7165 0.8280 0.4179 0.0184 1.0000 Uiso . . . . . . H391 H 0.8386 0.7776 0.5848 0.0242 1.0000 Uiso . . . . . . H392 H 0.6580 0.7111 0.5876 0.0242 1.0000 Uiso . . . . . . H401 H 0.7759 0.9241 0.7035 0.0296 1.0000 Uiso . . . . . . H402 H 0.8163 0.9862 0.6091 0.0296 1.0000 Uiso . . . . . . H411 H 0.5793 1.0229 0.6203 0.0298 1.0000 Uiso . . . . . . H412 H 0.4880 0.8705 0.6080 0.0298 1.0000 Uiso . . . . . . H421 H 0.5554 0.9791 0.4361 0.0261 1.0000 Uiso . . . . . . H422 H 0.3731 0.9173 0.4377 0.0261 1.0000 Uiso . . . . . . H431 H 0.4001 0.7104 0.4287 0.0196 1.0000 Uiso . . . . . . H441 H 0.2785 0.8589 0.2641 0.0229 1.0000 Uiso . . . . . . H461 H 0.0803 0.8805 0.1043 0.0284 1.0000 Uiso . . . . . . H471 H -0.0779 0.8215 -0.0892 0.0311 1.0000 Uiso . . . . . . H481 H -0.0575 0.6497 -0.2081 0.0296 1.0000 Uiso . . . . . . H511 H 0.5348 0.0634 0.0257 0.0229 1.0000 Uiso . . . . . . H512 H 0.3741 -0.0102 0.0497 0.0229 1.0000 Uiso . . . . . . H521 H 0.3023 -0.0443 -0.1429 0.0295 1.0000 Uiso . . . . . . H522 H 0.3625 0.1106 -0.1292 0.0295 1.0000 Uiso . . . . . . H523 H 0.2018 0.0371 -0.1051 0.0295 1.0000 Uiso . . . . . . H531 H 0.0516 0.5264 -0.2999 0.0286 1.0000 Uiso . . . . . . H532 H -0.0890 0.4292 -0.2704 0.0286 1.0000 Uiso . . . . . . H541 H -0.0035 0.3058 -0.3857 0.0311 1.0000 Uiso . . . . . . H542 H 0.1854 0.3697 -0.2981 0.0311 1.0000 Uiso . . . . . . H543 H 0.0448 0.2724 -0.2685 0.0311 1.0000 Uiso . . . . . . 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 0.0152(2) 0.0113(2) 0.0122(3) 0.0016(2) 0.0040(2) 0.0065(2) N1 0.0172(12) 0.0104(10) 0.0127(11) -0.0001(8) 0.0050(9) 0.0048(9) N2 0.0202(13) 0.0125(11) 0.0171(11) 0.0029(8) 0.0093(9) 0.0076(9) C1 0.0113(15) 0.0173(17) 0.020(2) 0.0108(14) 0.0081(14) 0.0108(13) C2 0.0160(17) 0.0218(19) 0.016(2) 0.0085(15) 0.0058(15) 0.0088(14) C3 0.0223(15) 0.0192(17) 0.0165(18) 0.0082(14) 0.0074(13) 0.0168(13) C4 0.0262(18) 0.028(2) 0.0083(15) 0.0048(13) 0.0008(13) 0.0150(15) C5 0.0188(18) 0.0234(18) 0.015(2) 0.0069(15) 0.0055(15) 0.0153(15) C6 0.0163(17) 0.0226(19) 0.014(2) 0.0053(15) 0.0070(16) 0.0092(15) C7 0.0159(14) 0.0180(14) 0.0112(13) 0.0022(10) 0.0066(11) 0.0065(11) C8 0.0200(10) 0.0125(9) 0.0172(9) 0.0007(7) 0.0105(8) 0.0047(8) C9 0.0287(19) 0.0203(18) 0.0176(19) 0.0025(14) 0.0052(15) 0.0102(14) C10 0.0427(17) 0.0248(13) 0.0204(11) -0.0007(10) 0.0120(12) 0.0125(12) C11 0.0364(14) 0.0173(10) 0.0271(12) -0.0052(9) 0.0117(11) 0.0079(10) C12 0.0283(17) 0.0190(15) 0.0252(17) 0.0008(12) 0.0122(14) 0.0106(13) C13 0.0196(10) 0.0119(8) 0.0170(9) -0.0007(7) 0.0086(8) 0.0037(7) C14 0.0230(15) 0.0162(14) 0.0268(17) 0.0081(12) 0.0139(13) 0.0112(12) C15 0.0186(19) 0.0152(19) 0.027(3) 0.0097(17) 0.0110(19) 0.0082(16) C16 0.0208(19) 0.022(2) 0.040(3) 0.0096(19) 0.0150(19) 0.0147(16) C17 0.0201(16) 0.0240(18) 0.031(2) 0.0118(15) 0.0074(15) 0.0164(14) C18 0.0217(16) 0.0256(17) 0.0251(19) 0.0085(14) 0.0059(14) 0.0095(13) C19 0.0145(14) 0.0169(15) 0.0208(19) 0.0080(13) 0.0028(13) 0.0053(11) C20 0.0176(18) 0.0156(18) 0.016(2) 0.0046(15) 0.0058(16) 0.0039(14) C21 0.0203(15) 0.0109(14) 0.0160(16) -0.0058(12) 0.0036(13) 0.0049(12) C22 0.031(2) 0.0207(17) 0.027(2) -0.0019(16) 0.0101(18) 0.0126(16) C23 0.0258(17) 0.0272(18) 0.0148(17) 0.0035(13) -0.0010(13) 0.0078(13) C24 0.035(2) 0.0236(16) 0.0159(17) 0.0027(13) 0.0026(14) 0.0086(14) O1 0.0174(14) 0.0133(13) 0.0144(16) 0.0036(12) 0.0051(12) 0.0088(11) O2 0.0211(15) 0.0184(15) 0.0162(17) 0.0056(13) 0.0032(13) 0.0092(12) O3 0.0235(13) 0.0160(13) 0.0151(16) -0.0017(11) 0.0010(12) 0.0114(11) O4 0.0182(11) 0.0254(12) 0.0148(12) 0.0045(9) 0.0024(9) 0.0123(9) O51 0.0399(15) 0.0397(17) 0.0211(15) 0.0106(13) 0.0112(12) 0.0261(13) Cu2 0.0153(2) 0.0130(2) 0.0126(3) 0.0015(2) 0.0044(2) 0.0071(2) N3 0.0157(12) 0.0151(11) 0.0142(11) 0.0007(8) 0.0052(9) 0.0051(9) N4 0.0178(12) 0.0157(11) 0.0162(10) 0.0035(8) 0.0081(9) 0.0062(9) C31 0.0179(17) 0.0122(16) 0.0082(16) -0.0026(12) 0.0048(14) 0.0038(13) C32 0.0180(17) 0.0093(14) 0.0128(18) -0.0013(12) 0.0065(15) 0.0065(13) C33 0.0225(17) 0.0176(17) 0.021(2) 0.0009(15) 0.0082(15) 0.0081(13) C34 0.0259(19) 0.0229(18) 0.029(2) 0.0087(16) 0.0121(17) 0.0209(16) C35 0.022(2) 0.026(2) 0.015(2) -0.0004(16) 0.0031(17) 0.0103(16) C36 0.0164(17) 0.0124(16) 0.0106(18) -0.0002(13) 0.0038(15) 0.0069(14) C37 0.0139(12) 0.0172(13) 0.0144(14) 0.0008(10) 0.0053(10) 0.0057(10) C38 0.0187(10) 0.0129(8) 0.0149(9) -0.0006(7) 0.0093(8) 0.0038(8) C39 0.0241(17) 0.0214(18) 0.0153(18) -0.0039(14) 0.0079(15) 0.0075(14) C40 0.0258(13) 0.0254(13) 0.0203(11) -0.0063(9) 0.0087(10) 0.0081(10) C41 0.0295(12) 0.0245(11) 0.0209(10) -0.0046(8) 0.0120(9) 0.0097(10) C42 0.0256(16) 0.0161(13) 0.0227(15) 0.0000(11) 0.0122(13) 0.0092(11) C43 0.0197(10) 0.0147(9) 0.0144(8) 0.0004(7) 0.0093(7) 0.0050(8) C44 0.0228(15) 0.0142(13) 0.0202(15) 0.0048(11) 0.0117(12) 0.0087(11) C45 0.0142(17) 0.0152(18) 0.020(2) 0.0043(16) 0.0074(17) 0.0078(15) C46 0.0208(18) 0.0184(19) 0.027(2) 0.0119(17) 0.0086(16) 0.0105(15) C47 0.0186(16) 0.027(2) 0.039(2) 0.0143(17) 0.0062(16) 0.0125(14) C48 0.0209(16) 0.0258(17) 0.027(2) 0.0137(15) 0.0043(14) 0.0132(13) C49 0.0176(15) 0.0193(16) 0.0206(19) 0.0071(14) 0.0074(14) 0.0090(12) C50 0.0119(16) 0.0163(18) 0.024(2) 0.0115(16) 0.0069(16) 0.0097(14) C51 0.0233(17) 0.0158(16) 0.027(2) 0.0061(14) 0.0124(16) 0.0117(13) C52 0.030(2) 0.0232(19) 0.0161(19) -0.0077(15) -0.0010(16) 0.0062(16) C53 0.0230(16) 0.0283(18) 0.0183(18) 0.0081(14) 0.0006(13) 0.0116(13) C54 0.0303(18) 0.032(2) 0.0162(17) 0.0060(14) 0.0059(14) 0.0101(15) O5 0.0217(15) 0.0173(15) 0.0118(16) 0.0012(12) 0.0009(13) 0.0109(12) O6 0.0167(14) 0.0165(14) 0.0172(17) 0.0023(12) 0.0043(13) 0.0120(11) O7 0.0271(15) 0.0182(14) 0.0156(16) -0.0010(12) 0.0024(13) 0.0127(12) O8 0.0243(12) 0.0226(12) 0.0168(12) 0.0034(10) 0.0038(10) 0.0114(10) O52 0.0395(15) 0.0341(15) 0.0172(14) 0.0072(11) 0.0084(11) 0.0247(12) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3303(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 Cu1 . N1 . 1.937(4) yes Cu1 . N2 . 1.956(3) yes Cu1 . O1 . 1.912(3) yes Cu1 . O2 . 1.915(4) yes N1 . C7 . 1.277(5) yes N1 . C8 . 1.478(4) yes N2 . C13 . 1.476(4) yes N2 . C14 . 1.305(6) yes C1 . C2 . 1.423(6) yes C1 . C6 . 1.405(7) yes C1 . O1 . 1.323(5) yes C2 . C3 . 1.401(6) yes C2 . O3 . 1.372(6) yes C3 . C4 . 1.407(7) yes C3 . H31 . 0.960 no C4 . C5 . 1.376(7) yes C4 . H41 . 0.962 no C5 . C6 . 1.414(6) yes C5 . H51 . 0.960 no C6 . C7 . 1.430(7) yes C7 . H71 . 0.961 no C8 . C9 . 1.517(6) yes C8 . C13 . 1.530(3) yes C8 . H81 . 0.960 no C9 . C10 . 1.525(6) yes C9 . H91 . 0.961 no C9 . H92 . 0.960 no C10 . C11 . 1.523(4) yes C10 . H101 . 0.960 no C10 . H102 . 0.961 no C11 . C12 . 1.525(6) yes C11 . H111 . 0.960 no C11 . H112 . 0.961 no C12 . C13 . 1.528(5) yes C12 . H121 . 0.959 no C12 . H122 . 0.959 no C13 . H131 . 0.960 no C14 . C15 . 1.409(8) yes C14 . H141 . 0.960 no C15 . C16 . 1.439(7) yes C15 . C20 . 1.429(7) yes C16 . C17 . 1.342(8) yes C16 . H161 . 0.957 no C17 . C18 . 1.418(8) yes C17 . H171 . 0.961 no C18 . C19 . 1.381(7) yes C18 . H181 . 0.958 no C19 . C20 . 1.450(8) yes C19 . O4 . 1.352(7) yes C20 . O2 . 1.288(6) yes C21 . C22 . 1.515(8) yes C21 . O3 . 1.452(5) yes C21 . H211 . 0.960 no C21 . H212 . 0.961 no C22 . H221 . 0.960 no C22 . H222 . 0.959 no C22 . H223 . 0.960 no C23 . C24 . 1.503(8) yes C23 . O4 . 1.445(7) yes C23 . H231 . 0.961 no C23 . H232 . 0.958 no C24 . H241 . 0.960 no C24 . H242 . 0.963 no C24 . H243 . 0.957 no O51 . H1 . 0.820 no O51 . H2 . 0.819 no Cu2 . N3 . 1.943(4) yes Cu2 . N4 . 1.944(3) yes Cu2 . O5 . 1.901(4) yes Cu2 . O6 . 1.893(4) yes N3 . C37 . 1.292(5) yes N3 . C38 . 1.481(4) yes N4 . C43 . 1.474(4) yes N4 . C44 . 1.270(6) yes C31 . C32 . 1.448(6) yes C31 . C36 . 1.428(6) yes C31 . O5 . 1.286(5) yes C32 . C33 . 1.347(6) yes C32 . O7 . 1.367(6) yes C33 . C34 . 1.404(8) yes C33 . H331 . 0.961 no C34 . C35 . 1.369(7) yes C34 . H341 . 0.959 no C35 . C36 . 1.419(6) yes C35 . H351 . 0.959 no C36 . C37 . 1.441(6) yes C37 . H371 . 0.960 no C38 . C39 . 1.530(6) yes C38 . C43 . 1.521(3) yes C38 . H381 . 0.961 no C39 . C40 . 1.539(6) yes C39 . H391 . 0.959 no C39 . H392 . 0.959 no C40 . C41 . 1.522(4) yes C40 . H401 . 0.960 no C40 . H402 . 0.961 no C41 . C42 . 1.523(6) yes C41 . H411 . 0.960 no C41 . H412 . 0.960 no C42 . C43 . 1.518(5) yes C42 . H421 . 0.961 no C42 . H422 . 0.961 no C43 . H431 . 0.959 no C44 . C45 . 1.466(7) yes C44 . H441 . 0.960 no C45 . C46 . 1.400(6) yes C45 . C50 . 1.411(7) yes C46 . C47 . 1.391(8) yes C46 . H461 . 0.962 no C47 . C48 . 1.392(8) yes C47 . H471 . 0.958 no C48 . C49 . 1.379(6) yes C48 . H481 . 0.962 no C49 . C50 . 1.412(8) yes C49 . O8 . 1.388(6) yes C50 . O6 . 1.319(5) yes C51 . C52 . 1.496(8) yes C51 . O7 . 1.416(6) yes C51 . H511 . 0.961 no C51 . H512 . 0.959 no C52 . H521 . 0.960 no C52 . H522 . 0.960 no C52 . H523 . 0.960 no C53 . C54 . 1.506(8) yes C53 . O8 . 1.425(7) yes C53 . H531 . 0.962 no C53 . H532 . 0.959 no C54 . H541 . 0.961 no C54 . H542 . 0.964 no C54 . H543 . 0.957 no O52 . H3 . 0.821 no O52 . H4 . 0.820 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 . Cu1 . N2 . 84.32(15) yes N1 . Cu1 . O1 . 93.25(14) yes N2 . Cu1 . O1 . 175.52(13) yes N1 . Cu1 . O2 . 176.79(15) yes N2 . Cu1 . O2 . 92.91(15) yes O1 . Cu1 . O2 . 89.41(15) yes Cu1 . N1 . C7 . 125.9(3) yes Cu1 . N1 . C8 . 112.8(2) yes C7 . N1 . C8 . 121.3(3) yes Cu1 . N2 . C13 . 111.9(2) yes Cu1 . N2 . C14 . 125.3(3) yes C13 . N2 . C14 . 122.8(3) yes C2 . C1 . C6 . 118.4(4) yes C2 . C1 . O1 . 116.5(4) yes C6 . C1 . O1 . 125.1(4) yes C1 . C2 . C3 . 121.0(4) yes C1 . C2 . O3 . 115.1(4) yes C3 . C2 . O3 . 123.9(4) yes C2 . C3 . C4 . 119.4(4) yes C2 . C3 . H31 . 120.2 no C4 . C3 . H31 . 120.4 no C3 . C4 . C5 . 120.0(4) yes C3 . C4 . H41 . 119.8 no C5 . C4 . H41 . 120.2 no C4 . C5 . C6 . 121.3(4) yes C4 . C5 . H51 . 119.5 no C6 . C5 . H51 . 119.2 no C5 . C6 . C1 . 119.7(4) yes C5 . C6 . C7 . 116.9(4) yes C1 . C6 . C7 . 122.9(4) yes C6 . C7 . N1 . 125.0(4) yes C6 . C7 . H71 . 117.3 no N1 . C7 . H71 . 117.7 no N1 . C8 . C9 . 117.2(3) yes N1 . C8 . C13 . 106.6(2) yes C9 . C8 . C13 . 111.5(2) yes N1 . C8 . H81 . 107.1 no C9 . C8 . H81 . 106.9 no C13 . C8 . H81 . 107.0 no C8 . C9 . C10 . 109.8(4) yes C8 . C9 . H91 . 109.4 no C10 . C9 . H91 . 109.4 no C8 . C9 . H92 . 109.5 no C10 . C9 . H92 . 109.4 no H91 . C9 . H92 . 109.3 no C9 . C10 . C11 . 111.5(3) yes C9 . C10 . H101 . 109.1 no C11 . C10 . H101 . 109.0 no C9 . C10 . H102 . 108.8 no C11 . C10 . H102 . 109.0 no H101 . C10 . H102 . 109.4 no C10 . C11 . C12 . 112.5(3) yes C10 . C11 . H111 . 108.8 no C12 . C11 . H111 . 108.8 no C10 . C11 . H112 . 108.6 no C12 . C11 . H112 . 108.7 no H111 . C11 . H112 . 109.4 no C11 . C12 . C13 . 109.7(3) yes C11 . C12 . H121 . 109.3 no C13 . C12 . H121 . 109.5 no C11 . C12 . H122 . 109.3 no C13 . C12 . H122 . 109.4 no H121 . C12 . H122 . 109.6 no C8 . C13 . C12 . 110.7(2) yes C8 . C13 . N2 . 106.90(19) yes C12 . C13 . N2 . 116.4(3) yes C8 . C13 . H131 . 107.5 no C12 . C13 . H131 . 107.5 no N2 . C13 . H131 . 107.5 no N2 . C14 . C15 . 125.2(4) yes N2 . C14 . H141 . 117.2 no C15 . C14 . H141 . 117.5 no C14 . C15 . C16 . 117.3(5) yes C14 . C15 . C20 . 122.4(5) yes C16 . C15 . C20 . 120.2(5) yes C15 . C16 . C17 . 121.7(5) yes C15 . C16 . H161 . 119.4 no C17 . C16 . H161 . 118.8 no C16 . C17 . C18 . 119.4(5) yes C16 . C17 . H171 . 120.6 no C18 . C17 . H171 . 120.0 no C17 . C18 . C19 . 121.3(5) yes C17 . C18 . H181 . 119.2 no C19 . C18 . H181 . 119.5 no C18 . C19 . C20 . 120.9(5) yes C18 . C19 . O4 . 126.1(5) yes C20 . C19 . O4 . 113.0(4) yes C19 . C20 . C15 . 116.4(5) yes C19 . C20 . O2 . 117.3(4) yes C15 . C20 . O2 . 126.3(5) yes C22 . C21 . O3 . 105.8(4) yes C22 . C21 . H211 . 110.7 no O3 . C21 . H211 . 110.5 no C22 . C21 . H212 . 110.2 no O3 . C21 . H212 . 110.1 no H211 . C21 . H212 . 109.4 no C21 . C22 . H221 . 109.2 no C21 . C22 . H222 . 109.4 no H221 . C22 . H222 . 109.5 no C21 . C22 . H223 . 109.7 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no C24 . C23 . O4 . 107.4(4) yes C24 . C23 . H231 . 110.0 no O4 . C23 . H231 . 109.8 no C24 . C23 . H232 . 110.0 no O4 . C23 . H232 . 110.2 no H231 . C23 . H232 . 109.5 no C23 . C24 . H241 . 109.9 no C23 . C24 . H242 . 109.2 no H241 . C24 . H242 . 109.2 no C23 . C24 . H243 . 109.4 no H241 . C24 . H243 . 109.7 no H242 . C24 . H243 . 109.5 no C1 . O1 . Cu1 . 125.6(3) yes C20 . O2 . Cu1 . 126.0(3) yes C21 . O3 . C2 . 118.2(4) yes C23 . O4 . C19 . 117.3(4) yes H1 . O51 . H2 . 109.6 no N3 . Cu2 . N4 . 84.30(16) yes N3 . Cu2 . O5 . 94.27(15) yes N4 . Cu2 . O5 . 165.55(13) yes N3 . Cu2 . O6 . 170.85(13) yes N4 . Cu2 . O6 . 94.00(14) yes O5 . Cu2 . O6 . 89.59(15) yes Cu2 . N3 . C37 . 125.2(3) yes Cu2 . N3 . C38 . 112.0(2) yes C37 . N3 . C38 . 122.6(3) yes Cu2 . N4 . C43 . 112.5(2) yes Cu2 . N4 . C44 . 125.8(3) yes C43 . N4 . C44 . 121.6(3) yes C32 . C31 . C36 . 115.2(4) yes C32 . C31 . O5 . 119.0(4) yes C36 . C31 . O5 . 125.9(4) yes C31 . C32 . C33 . 122.4(4) yes C31 . C32 . O7 . 111.7(4) yes C33 . C32 . O7 . 125.9(4) yes C32 . C33 . C34 . 121.4(4) yes C32 . C33 . H331 . 119.4 no C34 . C33 . H331 . 119.1 no C33 . C34 . C35 . 119.2(5) yes C33 . C34 . H341 . 120.6 no C35 . C34 . H341 . 120.2 no C34 . C35 . C36 . 120.8(5) yes C34 . C35 . H351 . 119.6 no C36 . C35 . H351 . 119.5 no C31 . C36 . C35 . 120.9(4) yes C31 . C36 . C37 . 122.2(4) yes C35 . C36 . C37 . 116.9(4) yes C36 . C37 . N3 . 125.5(4) yes C36 . C37 . H371 . 117.5 no N3 . C37 . H371 . 117.0 no N3 . C38 . C39 . 115.8(3) yes N3 . C38 . C43 . 107.0(2) yes C39 . C38 . C43 . 111.8(2) yes N3 . C38 . H381 . 107.2 no C39 . C38 . H381 . 107.2 no C43 . C38 . H381 . 107.5 no C38 . C39 . C40 . 109.6(4) yes C38 . C39 . H391 . 109.5 no C40 . C39 . H391 . 109.6 no C38 . C39 . H392 . 109.2 no C40 . C39 . H392 . 109.3 no H391 . C39 . H392 . 109.6 no C39 . C40 . C41 . 112.1(3) yes C39 . C40 . H401 . 108.7 no C41 . C40 . H401 . 108.9 no C39 . C40 . H402 . 108.8 no C41 . C40 . H402 . 108.9 no H401 . C40 . H402 . 109.5 no C40 . C41 . C42 . 112.4(3) yes C40 . C41 . H411 . 108.8 no C42 . C41 . H411 . 108.8 no C40 . C41 . H412 . 108.7 no C42 . C41 . H412 . 108.6 no H411 . C41 . H412 . 109.5 no C41 . C42 . C43 . 109.3(3) yes C41 . C42 . H421 . 109.6 no C43 . C42 . H421 . 109.6 no C41 . C42 . H422 . 109.6 no C43 . C42 . H422 . 109.4 no H421 . C42 . H422 . 109.3 no C38 . C43 . C42 . 111.2(2) yes C38 . C43 . N4 . 106.64(19) yes C42 . C43 . N4 . 117.2(3) yes C38 . C43 . H431 . 107.2 no C42 . C43 . H431 . 107.1 no N4 . C43 . H431 . 107.0 no N4 . C44 . C45 . 125.6(4) yes N4 . C44 . H441 . 117.4 no C45 . C44 . H441 . 117.0 no C44 . C45 . C46 . 116.9(4) yes C44 . C45 . C50 . 122.8(4) yes C46 . C45 . C50 . 120.2(5) yes C45 . C46 . C47 . 119.8(5) yes C45 . C46 . H461 . 119.8 no C47 . C46 . H461 . 120.4 no C46 . C47 . C48 . 121.0(5) yes C46 . C47 . H471 . 119.3 no C48 . C47 . H471 . 119.7 no C47 . C48 . C49 . 119.0(5) yes C47 . C48 . H481 . 120.6 no C49 . C48 . H481 . 120.4 no C48 . C49 . C50 . 121.9(5) yes C48 . C49 . O8 . 123.8(5) yes C50 . C49 . O8 . 114.3(4) yes C49 . C50 . C45 . 118.0(4) yes C49 . C50 . O6 . 118.0(4) yes C45 . C50 . O6 . 124.0(5) yes C52 . C51 . O7 . 108.0(4) yes C52 . C51 . H511 . 109.4 no O7 . C51 . H511 . 109.6 no C52 . C51 . H512 . 110.2 no O7 . C51 . H512 . 110.1 no H511 . C51 . H512 . 109.5 no C51 . C52 . H521 . 109.8 no C51 . C52 . H522 . 109.7 no H521 . C52 . H522 . 109.4 no C51 . C52 . H523 . 109.0 no H521 . C52 . H523 . 109.5 no H522 . C52 . H523 . 109.4 no C54 . C53 . O8 . 107.0(4) yes C54 . C53 . H531 . 110.0 no O8 . C53 . H531 . 109.9 no C54 . C53 . H532 . 110.1 no O8 . C53 . H532 . 110.3 no H531 . C53 . H532 . 109.4 no C53 . C54 . H541 . 109.3 no C53 . C54 . H542 . 109.7 no H541 . C54 . H542 . 109.1 no C53 . C54 . H543 . 109.8 no H541 . C54 . H543 . 109.6 no H542 . C54 . H543 . 109.4 no C31 . O5 . Cu2 . 126.7(3) yes C50 . O6 . Cu2 . 127.8(3) yes C51 . O7 . C32 . 118.0(4) yes C53 . O8 . C49 . 117.4(4) yes H3 . O52 . H4 . 109.4 no