# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Edwin Constable' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Valerie Chaurin' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Catherine E. Housecroft' '' '' 'Markus Neuburger' '' '' 'Silvia Schaffner' '' '' _publ_contact_author_name 'Edwin Constable' _publ_contact_author_address ; Departement Chemie University of Basel Spitalstrasse 51 Basel CH-4056 SWITZERLAND ; _publ_contact_author_email EDWIN.CONSTABLE@UNIBAS.CH _publ_requested_journal CrystEngComm _publ_section_title ; The aryl-phen and phen-phen embraces - new supramolecular motifs ; _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_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _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' data_chaurinCuHe _database_code_depnum_ccdc_archive 'CCDC 675350' _audit_creation_date 07-12-06 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '12100940 chaurinCuHe_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 10.1491(3) _cell_length_b 11.4654(3) _cell_length_c 15.1523(4) _cell_angle_alpha 71.8196(16) _cell_angle_beta 82.5003(13) _cell_angle_gamma 82.8793(17) _cell_volume 1654.33(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 -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' 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' 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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C38 H28 Cu1 F6 N4 O2 P1 # Dc = 1.57 Fooo = 796.00 Mu = 7.85 M = 781.17 # Found Formula = C38 H28 Cu1 F6 N4 O2 P1 # Dc = 1.57 FOOO = 796.00 Mu = 7.85 M = 781.17 _chemical_formula_sum 'C38 H28 Cu1 F6 N4 O2 P1' _chemical_formula_moiety 'C38 H28 Cu N4 O2, F6 P' _chemical_compound_source ? _chemical_formula_weight 781.17 _cell_measurement_reflns_used 7411 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_max 0.28 _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 0.785 # Sheldrick geometric approximatio 0.84 0.97 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.84 _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 173 _diffrn_reflns_number 14503 _reflns_number_total 7534 _diffrn_reflns_av_R_equivalents 0.016 # Number of reflections with Friedels Law is 7534 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7560 _diffrn_reflns_theta_min 2.364 _diffrn_reflns_theta_max 27.486 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.936 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -12 _reflns_limit_h_max 13 _reflns_limit_k_min -13 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _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 -0.36 _refine_diff_density_max 0.33 _refine_ls_number_reflns 5280 _refine_ls_number_restraints 784 _refine_ls_number_parameters 523 #_refine_ls_R_factor_ref 0.0380 _refine_ls_wR_factor_ref 0.0447 _refine_ls_goodness_of_fit_ref 1.1026 #_reflns_number_all 7460 _refine_ls_R_factor_all 0.0576 _refine_ls_wR_factor_all 0.0615 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.5\s(I) _reflns_number_gt 5280 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_gt 0.0447 _refine_ls_shift/su_max 0.001303 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.661 0.530 0.357 ; _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. 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 0.48583(3) 0.63222(3) 0.749326(19) 0.0399 1.0000 Uani . . . . . . N1 N 0.62425(19) 0.58575(16) 0.83940(13) 0.0396 1.0000 Uani . . . . . . N2 N 0.36908(18) 0.67967(15) 0.86052(12) 0.0344 1.0000 Uani . . . . . . N3 N 0.43309(19) 0.56121(17) 0.65552(13) 0.0406 1.0000 Uani . . . . . . N4 N 0.44601(17) 0.79813(17) 0.64448(12) 0.0361 1.0000 Uani . . . . . . C1 C 0.7489(2) 0.5373(2) 0.83003(18) 0.0479 1.0000 Uani . . . . . . C2 C 0.8403(3) 0.5222(3) 0.8956(2) 0.0566 1.0000 Uani . . . . . . C3 C 0.8019(3) 0.5588(2) 0.97259(19) 0.0531 1.0000 Uani . . . . . . C4 C 0.6698(2) 0.6101(2) 0.98645(16) 0.0446 1.0000 Uani . . . . . . C5 C 0.5840(2) 0.62027(19) 0.91802(14) 0.0371 1.0000 Uani . . . . . . C6 C 0.6210(3) 0.6532(2) 1.06481(17) 0.0519 1.0000 Uani . . . . . . C7 C 0.4950(3) 0.7049(2) 1.07325(17) 0.0504 1.0000 Uani . . . . . . C8 C 0.4049(3) 0.7174(2) 1.00474(15) 0.0432 1.0000 Uani . . . . . . C9 C 0.4484(2) 0.67280(18) 0.92795(14) 0.0366 1.0000 Uani . . . . . . C10 C 0.2740(3) 0.7735(2) 1.00908(17) 0.0481 1.0000 Uani . . . . . . C11 C 0.1962(3) 0.7850(2) 0.93930(17) 0.0466 1.0000 Uani . . . . . . C12 C 0.2461(2) 0.73539(19) 0.86566(15) 0.0382 1.0000 Uani . . . . . . C13 C 0.1612(2) 0.7453(2) 0.79081(15) 0.0376 1.0000 Uani . . . . . . C14 C 0.1479(2) 0.6445(2) 0.76134(15) 0.0392 1.0000 Uani . . . . . . C15 C 0.0685(2) 0.6535(2) 0.69110(16) 0.0426 1.0000 Uani . . . . . . C16 C 0.0037(2) 0.7669(2) 0.64799(17) 0.0463 1.0000 Uani . . . . . . C17 C 0.0173(2) 0.8692(2) 0.67542(18) 0.0493 1.0000 Uani . . . . . . C18 C 0.0935(2) 0.8587(2) 0.74685(17) 0.0441 1.0000 Uani . . . . . . C19 C -0.0910(3) 0.6867(3) 0.5451(2) 0.0678 1.0000 Uani . . . . . . C20 C 0.4275(3) 0.4439(2) 0.66064(18) 0.0506 1.0000 Uani . . . . . . C21 C 0.3726(3) 0.4074(3) 0.5945(2) 0.0613 1.0000 Uani . . . . . . C22 C 0.3204(3) 0.4958(3) 0.5208(2) 0.0594 1.0000 Uani . . . . . . C23 C 0.3228(2) 0.6208(3) 0.51235(17) 0.0495 1.0000 Uani . . . . . . C24 C 0.3822(2) 0.6495(2) 0.58124(15) 0.0407 1.0000 Uani . . . . . . C25 C 0.2652(3) 0.7194(3) 0.43957(18) 0.0572 1.0000 Uani . . . . . . C26 C 0.2614(3) 0.8376(3) 0.43882(18) 0.0558 1.0000 Uani . . . . . . C27 C 0.3182(2) 0.8697(2) 0.50962(16) 0.0456 1.0000 Uani . . . . . . C28 C 0.3842(2) 0.7758(2) 0.57748(15) 0.0392 1.0000 Uani . . . . . . C29 C 0.3074(3) 0.9894(2) 0.51687(17) 0.0499 1.0000 Uani . . . . . . C30 C 0.3642(3) 1.0113(2) 0.58670(17) 0.0476 1.0000 Uani . . . . . . C31 C 0.4370(2) 0.9136(2) 0.64899(15) 0.0387 1.0000 Uani . . . . . . C32 C 0.5059(2) 0.93452(19) 0.72217(15) 0.0384 1.0000 Uani . . . . . . C33 C 0.6341(2) 0.8809(2) 0.73905(15) 0.0393 1.0000 Uani . . . . . . C34 C 0.6988(2) 0.8965(2) 0.80942(16) 0.0424 1.0000 Uani . . . . . . C35 C 0.6315(3) 0.9637(2) 0.86595(17) 0.0454 1.0000 Uani . . . . . . C36 C 0.5027(3) 1.0171(2) 0.85062(19) 0.0506 1.0000 Uani . . . . . . C37 C 0.4409(2) 1.0047(2) 0.77840(18) 0.0459 1.0000 Uani . . . . . . C38 C 0.8159(3) 0.9284(3) 0.9575(2) 0.0629 1.0000 Uani . . . . . . O1 O -0.0761(2) 0.7877(2) 0.57763(15) 0.0630 1.0000 Uani . . . . . . O2 O 0.6832(2) 0.9810(2) 0.93941(14) 0.0604 1.0000 Uani . . . . . . P1 P 0.03762(8) 0.24780(6) 0.75593(5) 0.0552 1.0000 Uani D U . . . . F1 F -0.0767(7) 0.1807(7) 0.7449(7) 0.1266 0.3500 Uani D U . . . . F2 F 0.1631(8) 0.3062(8) 0.7748(5) 0.1138 0.3500 Uani D U . . . . F3 F -0.0125(9) 0.3701(6) 0.6908(5) 0.1095 0.3500 Uani D U . . . . F4 F 0.0992(6) 0.1167(5) 0.8264(4) 0.0720 0.3500 Uani D U . . . . F5 F -0.0367(9) 0.2757(7) 0.8440(5) 0.1521 0.3500 Uani D U . . . . F6 F 0.1289(9) 0.2083(7) 0.6776(4) 0.1170 0.3500 Uani D U . . . . F11 F -0.0167(5) 0.1684(3) 0.7006(3) 0.0957 0.6500 Uani D U . . . . F12 F 0.0796(6) 0.3347(4) 0.8059(4) 0.1225 0.6500 Uani D U . . . . F13 F 0.0301(5) 0.3627(4) 0.6614(3) 0.0896 0.6500 Uani D U . . . . F14 F 0.0329(5) 0.1377(4) 0.8459(3) 0.1149 0.6500 Uani D U . . . . F15 F -0.1150(4) 0.2906(5) 0.7789(3) 0.1257 0.6500 Uani D U . . . . F16 F 0.1796(4) 0.2116(4) 0.7235(5) 0.1621 0.6500 Uani D U . . . . H11 H 0.7794 0.5102 0.7734 0.0548 1.0000 Uiso R . . . . . H21 H 0.9332 0.4845 0.8856 0.0635 1.0000 Uiso R . . . . . H31 H 0.8667 0.5496 1.0193 0.0612 1.0000 Uiso R . . . . . H61 H 0.6813 0.6447 1.1140 0.0624 1.0000 Uiso R . . . . . H71 H 0.4639 0.7351 1.1283 0.0613 1.0000 Uiso R . . . . . H101 H 0.2381 0.8048 1.0629 0.0587 1.0000 Uiso R . . . . . H111 H 0.1044 0.8282 0.9403 0.0567 1.0000 Uiso R . . . . . H141 H 0.1968 0.5634 0.7915 0.0465 1.0000 Uiso R . . . . . H151 H 0.0583 0.5794 0.6720 0.0519 1.0000 Uiso R . . . . . H171 H -0.0284 0.9511 0.6431 0.0585 1.0000 Uiso R . . . . . H181 H 0.1005 0.9323 0.7675 0.0534 1.0000 Uiso R . . . . . H191 H -0.1515 0.7143 0.4939 0.0849 1.0000 Uiso R . . . . . H192 H -0.1301 0.6192 0.5977 0.0849 1.0000 Uiso R . . . . . H193 H -0.0017 0.6555 0.5207 0.0849 1.0000 Uiso R . . . . . H201 H 0.4644 0.3784 0.7146 0.0613 1.0000 Uiso R . . . . . H211 H 0.3714 0.3180 0.6010 0.0773 1.0000 Uiso R . . . . . H221 H 0.2808 0.4712 0.4729 0.0766 1.0000 Uiso R . . . . . H251 H 0.2273 0.7001 0.3886 0.0709 1.0000 Uiso R . . . . . H261 H 0.2185 0.9043 0.3882 0.0654 1.0000 Uiso R . . . . . H291 H 0.2586 1.0585 0.4713 0.0555 1.0000 Uiso R . . . . . H301 H 0.3542 1.0959 0.5938 0.0546 1.0000 Uiso R . . . . . H331 H 0.6809 0.8298 0.6996 0.0463 1.0000 Uiso R . . . . . H341 H 0.7924 0.8599 0.8191 0.0505 1.0000 Uiso R . . . . . H361 H 0.4544 1.0648 0.8921 0.0640 1.0000 Uiso R . . . . . H371 H 0.3495 1.0461 0.7663 0.0555 1.0000 Uiso R . . . . . H381 H 0.8413 0.9478 1.0127 0.0783 1.0000 Uiso R . . . . . H382 H 0.8790 0.9639 0.9016 0.0783 1.0000 Uiso R . . . . . H383 H 0.8203 0.8370 0.9707 0.0783 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 0.04431(16) 0.04039(15) 0.03479(14) -0.01000(11) -0.00827(10) -0.00126(11) N1 0.0389(9) 0.0355(9) 0.0396(9) -0.0031(7) -0.0068(7) -0.0031(7) N2 0.0390(9) 0.0309(8) 0.0318(8) -0.0065(7) -0.0038(7) -0.0050(7) N3 0.0436(10) 0.0412(10) 0.0394(9) -0.0160(8) -0.0009(8) -0.0059(8) N4 0.0343(9) 0.0413(9) 0.0317(8) -0.0091(7) -0.0028(7) -0.0045(7) C1 0.0409(12) 0.0492(13) 0.0472(13) -0.0055(10) -0.0062(10) -0.0024(10) C2 0.0404(13) 0.0596(15) 0.0589(15) 0.0008(12) -0.0117(11) -0.0049(11) C3 0.0483(13) 0.0542(14) 0.0509(14) 0.0016(11) -0.0199(11) -0.0117(11) C4 0.0509(13) 0.0378(11) 0.0410(12) 0.0019(9) -0.0145(10) -0.0145(10) C5 0.0429(11) 0.0314(10) 0.0339(10) -0.0011(8) -0.0086(9) -0.0093(8) C6 0.0711(17) 0.0466(13) 0.0387(12) -0.0028(10) -0.0220(11) -0.0166(12) C7 0.0723(17) 0.0470(13) 0.0344(11) -0.0096(10) -0.0124(11) -0.0143(12) C8 0.0589(14) 0.0372(11) 0.0334(10) -0.0069(9) -0.0062(10) -0.0122(10) C9 0.0446(11) 0.0300(10) 0.0335(10) -0.0043(8) -0.0072(8) -0.0077(8) C10 0.0614(15) 0.0462(12) 0.0392(12) -0.0175(10) 0.0007(11) -0.0081(11) C11 0.0478(13) 0.0481(13) 0.0458(12) -0.0186(10) -0.0016(10) -0.0021(10) C12 0.0422(11) 0.0337(10) 0.0373(10) -0.0084(8) -0.0027(9) -0.0057(8) C13 0.0343(10) 0.0397(11) 0.0369(10) -0.0090(9) -0.0025(8) -0.0040(8) C14 0.0379(11) 0.0387(11) 0.0394(11) -0.0087(9) -0.0052(9) -0.0037(9) C15 0.0409(12) 0.0458(12) 0.0432(12) -0.0151(10) -0.0037(9) -0.0074(9) C16 0.0352(11) 0.0591(14) 0.0462(12) -0.0168(11) -0.0102(9) -0.0013(10) C17 0.0412(12) 0.0471(13) 0.0580(14) -0.0136(11) -0.0157(11) 0.0081(10) C18 0.0392(12) 0.0431(12) 0.0513(13) -0.0169(10) -0.0065(10) 0.0006(9) C19 0.0674(18) 0.083(2) 0.0628(17) -0.0262(15) -0.0242(14) -0.0117(15) C20 0.0602(15) 0.0484(13) 0.0446(13) -0.0176(11) 0.0045(11) -0.0113(11) C21 0.0735(18) 0.0565(15) 0.0636(16) -0.0310(14) 0.0088(14) -0.0242(14) C22 0.0586(16) 0.0766(18) 0.0564(15) -0.0344(14) 0.0002(13) -0.0247(14) C23 0.0437(12) 0.0680(16) 0.0434(12) -0.0237(11) -0.0013(10) -0.0148(11) C24 0.0374(11) 0.0514(13) 0.0350(10) -0.0148(9) -0.0020(9) -0.0076(9) C25 0.0515(14) 0.0828(19) 0.0432(13) -0.0225(13) -0.0110(11) -0.0121(13) C26 0.0470(14) 0.0758(18) 0.0405(12) -0.0093(12) -0.0131(10) -0.0022(12) C27 0.0379(11) 0.0585(14) 0.0371(11) -0.0084(10) -0.0059(9) -0.0046(10) C28 0.0346(10) 0.0477(12) 0.0327(10) -0.0086(9) -0.0015(8) -0.0045(9) C29 0.0466(13) 0.0496(13) 0.0427(12) 0.0010(10) -0.0087(10) 0.0019(10) C30 0.0486(13) 0.0402(12) 0.0480(13) -0.0060(10) -0.0047(10) -0.0006(10) C31 0.0380(11) 0.0384(11) 0.0367(11) -0.0073(9) -0.0005(9) -0.0055(9) C32 0.0427(11) 0.0341(10) 0.0379(11) -0.0088(9) -0.0035(9) -0.0078(9) C33 0.0435(11) 0.0354(10) 0.0373(11) -0.0079(9) -0.0025(9) -0.0062(9) C34 0.0408(11) 0.0412(11) 0.0439(12) -0.0082(9) -0.0036(9) -0.0113(9) C35 0.0502(13) 0.0465(12) 0.0433(12) -0.0154(10) -0.0026(10) -0.0158(10) C36 0.0516(14) 0.0515(14) 0.0569(14) -0.0285(12) 0.0011(11) -0.0101(11) C37 0.0435(12) 0.0408(12) 0.0543(13) -0.0164(10) -0.0007(10) -0.0058(9) C38 0.0692(18) 0.0666(17) 0.0601(16) -0.0192(14) -0.0242(14) -0.0145(14) O1 0.0570(11) 0.0721(12) 0.0663(12) -0.0251(10) -0.0306(9) 0.0069(9) O2 0.0632(12) 0.0735(12) 0.0566(11) -0.0324(10) -0.0088(9) -0.0149(10) P1 0.0604(4) 0.0475(4) 0.0557(4) -0.0159(3) 0.0035(3) -0.0066(3) F1 0.093(4) 0.110(5) 0.160(6) 0.019(5) -0.066(4) -0.047(4) F2 0.134(5) 0.148(6) 0.076(4) -0.028(4) -0.001(4) -0.099(4) F3 0.144(5) 0.050(3) 0.119(6) -0.015(4) -0.019(5) 0.025(4) F4 0.092(4) 0.071(3) 0.057(3) -0.022(3) -0.028(3) 0.011(3) F5 0.185(5) 0.133(5) 0.115(5) -0.054(4) 0.081(5) 0.020(5) F6 0.162(6) 0.131(5) 0.053(3) -0.046(3) -0.008(4) 0.049(5) F11 0.139(4) 0.0584(17) 0.103(3) -0.0375(19) -0.043(2) 0.006(2) F12 0.183(4) 0.088(2) 0.120(3) -0.039(2) -0.064(3) -0.023(3) F13 0.139(3) 0.0523(19) 0.066(2) -0.0090(15) -0.001(2) 0.001(2) F14 0.153(4) 0.102(3) 0.074(2) 0.027(2) -0.040(3) -0.063(3) F15 0.084(2) 0.167(4) 0.121(3) -0.054(3) 0.022(2) 0.002(3) F16 0.067(2) 0.108(3) 0.246(6) 0.004(4) 0.040(3) 0.027(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4340(6) 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 . 1.9953(19) yes Cu1 . N2 . 2.1047(18) yes Cu1 . N3 . 1.9995(19) yes Cu1 . N4 . 2.0969(18) yes N1 . C1 . 1.326(3) yes N1 . C5 . 1.367(3) yes N2 . C9 . 1.359(3) yes N2 . C12 . 1.335(3) yes N3 . C20 . 1.331(3) yes N3 . C24 . 1.367(3) yes N4 . C28 . 1.363(3) yes N4 . C31 . 1.338(3) yes C1 . C2 . 1.405(4) yes C1 . H11 . 1.000 no C2 . C3 . 1.354(4) yes C2 . H21 . 1.000 no C3 . C4 . 1.413(4) yes C3 . H31 . 1.000 no C4 . C5 . 1.408(3) yes C4 . C6 . 1.432(4) yes C5 . C9 . 1.441(3) yes C6 . C7 . 1.349(4) yes C6 . H61 . 1.000 no C7 . C8 . 1.434(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.411(3) yes C8 . C10 . 1.404(4) yes C10 . C11 . 1.365(4) yes C10 . H101 . 1.000 no C11 . C12 . 1.415(3) yes C11 . H111 . 1.000 no C12 . C13 . 1.480(3) yes C13 . C14 . 1.389(3) yes C13 . C18 . 1.401(3) yes C14 . C15 . 1.388(3) yes C14 . H141 . 1.000 no C15 . C16 . 1.386(3) yes C15 . H151 . 1.000 no C16 . C17 . 1.388(4) yes C16 . O1 . 1.367(3) yes C17 . C18 . 1.378(3) yes C17 . H171 . 1.000 no C18 . H181 . 1.000 no C19 . O1 . 1.424(4) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . C21 . 1.398(4) yes C20 . H201 . 1.000 no C21 . C22 . 1.367(4) yes C21 . H211 . 1.000 no C22 . C23 . 1.402(4) yes C22 . H221 . 1.000 no C23 . C24 . 1.410(3) yes C23 . C25 . 1.436(4) yes C24 . C28 . 1.434(3) yes C25 . C26 . 1.348(4) yes C25 . H251 . 1.000 no C26 . C27 . 1.441(4) yes C26 . H261 . 1.000 no C27 . C28 . 1.406(3) yes C27 . C29 . 1.400(4) yes C29 . C30 . 1.369(4) yes C29 . H291 . 1.000 no C30 . C31 . 1.417(3) yes C30 . H301 . 1.000 no C31 . C32 . 1.478(3) yes C32 . C33 . 1.388(3) yes C32 . C37 . 1.400(3) yes C33 . C34 . 1.390(3) yes C33 . H331 . 1.000 no C34 . C35 . 1.386(3) yes C34 . H341 . 1.000 no C35 . C36 . 1.389(4) yes C35 . O2 . 1.368(3) yes C36 . C37 . 1.381(4) yes C36 . H361 . 1.000 no C37 . H371 . 1.000 no C38 . O2 . 1.430(4) yes C38 . H381 . 1.000 no C38 . H382 . 1.000 no C38 . H383 . 1.000 no P1 . F1 . 1.522(5) yes P1 . F2 . 1.606(5) yes P1 . F3 . 1.513(6) yes P1 . F4 . 1.652(5) yes P1 . F5 . 1.549(5) yes P1 . F6 . 1.555(5) yes P1 . F11 . 1.599(3) yes P1 . F12 . 1.552(4) yes P1 . F13 . 1.619(3) yes P1 . F14 . 1.542(3) yes P1 . F15 . 1.593(3) yes P1 . F16 . 1.511(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 . Cu1 . N2 . 82.23(7) yes N1 . Cu1 . N3 . 135.20(8) yes N2 . Cu1 . N3 . 129.68(7) yes N1 . Cu1 . N4 . 129.84(7) yes N2 . Cu1 . N4 . 97.58(7) yes N3 . Cu1 . N4 . 81.96(7) yes Cu1 . N1 . C1 . 129.58(17) yes Cu1 . N1 . C5 . 112.71(14) yes C1 . N1 . C5 . 117.4(2) yes Cu1 . N2 . C9 . 109.21(14) yes Cu1 . N2 . C12 . 131.00(14) yes C9 . N2 . C12 . 118.19(19) yes Cu1 . N3 . C20 . 129.49(17) yes Cu1 . N3 . C24 . 112.57(15) yes C20 . N3 . C24 . 117.5(2) yes Cu1 . N4 . C28 . 109.46(14) yes Cu1 . N4 . C31 . 128.81(14) yes C28 . N4 . C31 . 118.46(19) yes N1 . C1 . C2 . 123.2(3) yes N1 . C1 . H11 . 118.4 no C2 . C1 . H11 . 118.4 no C1 . C2 . C3 . 119.6(3) yes C1 . C2 . H21 . 120.2 no C3 . C2 . H21 . 120.2 no C2 . C3 . C4 . 119.5(2) yes C2 . C3 . H31 . 120.2 no C4 . C3 . H31 . 120.2 no C3 . C4 . C5 . 117.2(2) yes C3 . C4 . C6 . 123.4(2) yes C5 . C4 . C6 . 119.3(2) yes C4 . C5 . N1 . 122.9(2) yes C4 . C5 . C9 . 119.8(2) yes N1 . C5 . C9 . 117.25(19) yes C4 . C6 . C7 . 121.1(2) yes C4 . C6 . H61 . 119.5 no C7 . C6 . H61 . 119.5 no C6 . C7 . C8 . 121.2(2) yes C6 . C7 . H71 . 119.4 no C8 . C7 . H71 . 119.4 no C7 . C8 . C9 . 119.2(2) yes C7 . C8 . C10 . 123.4(2) yes C9 . C8 . C10 . 117.4(2) yes C5 . C9 . C8 . 119.3(2) yes C5 . C9 . N2 . 117.61(19) yes C8 . C9 . N2 . 123.0(2) yes C8 . C10 . C11 . 119.6(2) yes C8 . C10 . H101 . 120.2 no C11 . C10 . H101 . 120.2 no C10 . C11 . C12 . 119.7(2) yes C10 . C11 . H111 . 120.2 no C12 . C11 . H111 . 120.2 no C11 . C12 . N2 . 122.1(2) yes C11 . C12 . C13 . 119.9(2) yes N2 . C12 . C13 . 117.98(19) yes C12 . C13 . C14 . 121.55(19) yes C12 . C13 . C18 . 120.1(2) yes C14 . C13 . C18 . 118.4(2) yes C13 . C14 . C15 . 121.7(2) yes C13 . C14 . H141 . 119.1 no C15 . C14 . H141 . 119.1 no C14 . C15 . C16 . 118.8(2) yes C14 . C15 . H151 . 120.6 no C16 . C15 . H151 . 120.6 no C15 . C16 . C17 . 120.3(2) yes C15 . C16 . O1 . 124.4(2) yes C17 . C16 . O1 . 115.3(2) yes C16 . C17 . C18 . 120.4(2) yes C16 . C17 . H171 . 119.8 no C18 . C17 . H171 . 119.8 no C13 . C18 . C17 . 120.3(2) yes C13 . C18 . H181 . 119.8 no C17 . C18 . H181 . 119.8 no O1 . C19 . H191 . 109.5 no O1 . C19 . H192 . 109.5 no H191 . C19 . H192 . 109.5 no O1 . C19 . H193 . 109.4 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no N3 . C20 . C21 . 123.4(3) yes N3 . C20 . H201 . 118.3 no C21 . C20 . H201 . 118.3 no C20 . C21 . C22 . 119.0(3) yes C20 . C21 . H211 . 120.5 no C22 . C21 . H211 . 120.5 no C21 . C22 . C23 . 120.0(2) yes C21 . C22 . H221 . 120.0 no C23 . C22 . H221 . 120.0 no C22 . C23 . C24 . 117.3(2) yes C22 . C23 . C25 . 123.7(2) yes C24 . C23 . C25 . 119.0(2) yes C23 . C24 . N3 . 122.8(2) yes C23 . C24 . C28 . 119.7(2) yes N3 . C24 . C28 . 117.4(2) yes C23 . C25 . C26 . 121.1(2) yes C23 . C25 . H251 . 119.4 no C26 . C25 . H251 . 119.4 no C25 . C26 . C27 . 121.2(2) yes C25 . C26 . H261 . 119.4 no C27 . C26 . H261 . 119.4 no C26 . C27 . C28 . 118.8(2) yes C26 . C27 . C29 . 123.6(2) yes C28 . C27 . C29 . 117.6(2) yes C24 . C28 . C27 . 119.9(2) yes C24 . C28 . N4 . 117.1(2) yes C27 . C28 . N4 . 122.9(2) yes C27 . C29 . C30 . 119.6(2) yes C27 . C29 . H291 . 120.2 no C30 . C29 . H291 . 120.2 no C29 . C30 . C31 . 119.8(2) yes C29 . C30 . H301 . 120.1 no C31 . C30 . H301 . 120.1 no C30 . C31 . N4 . 121.5(2) yes C30 . C31 . C32 . 121.5(2) yes N4 . C31 . C32 . 116.98(19) yes C31 . C32 . C33 . 120.7(2) yes C31 . C32 . C37 . 120.6(2) yes C33 . C32 . C37 . 118.7(2) yes C32 . C33 . C34 . 121.5(2) yes C32 . C33 . H331 . 119.2 no C34 . C33 . H331 . 119.3 no C33 . C34 . C35 . 118.9(2) yes C33 . C34 . H341 . 120.5 no C35 . C34 . H341 . 120.5 no C34 . C35 . C36 . 120.3(2) yes C34 . C35 . O2 . 124.0(2) yes C36 . C35 . O2 . 115.6(2) yes C35 . C36 . C37 . 120.3(2) yes C35 . C36 . H361 . 119.8 no C37 . C36 . H361 . 119.9 no C32 . C37 . C36 . 120.2(2) yes C32 . C37 . H371 . 119.9 no C36 . C37 . H371 . 119.9 no O2 . C38 . H381 . 109.5 no O2 . C38 . H382 . 109.3 no H381 . C38 . H382 . 109.5 no O2 . C38 . H383 . 109.5 no H381 . C38 . H383 . 109.5 no H382 . C38 . H383 . 109.5 no C19 . O1 . C16 . 117.7(2) yes C38 . O2 . C35 . 117.7(2) yes F1 . P1 . F2 . 174.4(4) yes F1 . P1 . F3 . 93.8(4) yes F2 . P1 . F3 . 91.8(4) yes F1 . P1 . F4 . 88.7(3) yes F2 . P1 . F4 . 85.7(3) yes F3 . P1 . F4 . 177.3(4) yes F1 . P1 . F5 . 92.2(4) yes F2 . P1 . F5 . 87.1(4) yes F3 . P1 . F5 . 93.5(4) yes F4 . P1 . F5 . 87.3(3) yes F1 . P1 . F6 . 92.0(4) yes F2 . P1 . F6 . 87.9(4) yes F3 . P1 . F6 . 94.0(4) yes F4 . P1 . F6 . 85.0(3) yes F5 . P1 . F6 . 171.1(4) yes F11 . P1 . F12 . 174.5(2) yes F11 . P1 . F13 . 87.0(2) yes F12 . P1 . F13 . 89.2(2) yes F11 . P1 . F14 . 90.6(2) yes F12 . P1 . F14 . 92.9(2) yes F13 . P1 . F14 . 175.5(3) yes F11 . P1 . F15 . 86.1(2) yes F12 . P1 . F15 . 89.6(3) yes F13 . P1 . F15 . 85.1(2) yes F14 . P1 . F15 . 90.9(2) yes F11 . P1 . F16 . 90.3(3) yes F12 . P1 . F16 . 93.7(3) yes F13 . P1 . F16 . 89.9(2) yes F14 . P1 . F16 . 94.0(3) yes F15 . P1 . F16 . 174.0(3) yes