# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address _publ_author_email 'Martin Baumgarten' ; Max-Planck-Institute for Polymer Research Ackermannweg 10 D-55021 Mainz Germany ; ; ve@mpip-mainz.mpg.de ; 'Yulia Borozdina' ; Max-Planck-Institute for Polymer Research Ackermannweg 10 D-55021 Mainz Germany ; ; baumgart@mpip-mainz.mpg.de ; F.Laquai '' '' V.Kamm '' '' _publ_contact_author_address ; Max-Planck-Institute for Polymer Research Ackermannweg 10 D-55021 Mainz Germany ; _publ_contact_author_email borozdin@mpip-mainz.mpg.de _publ_contact_author_fax '+49 379514' _publ_contact_author_phone '+49 379154' # 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_contact_author_name 'Yulia Borozdina' # Attachment '4556_web_deposit_cif_file_1_YuliaBorozdina_1299676307.cif' data_baumyul2 _database_code_depnum_ccdc_archive 'CCDC 816631' #TrackingRef '4556_web_deposit_cif_file_1_YuliaBorozdina_1299676307.cif' _audit_creation_date 09-08-10 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.3261(2) _cell_length_b 29.7850(9) _cell_length_c 9.8773(3) _cell_angle_alpha 90 _cell_angle_beta 109.2812(16) _cell_angle_gamma 90 _cell_volume 2034.41(11) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z 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' 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' 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' _cell_formula_units_Z 4 # Given Formula = C26 H23 N4 O1 # Dc = 1.33 Fooo = 860.00 Mu = 0.83 M = 407.49 # Found Formula = C26 H23 N4 O1 # Dc = 1.33 FOOO = 860.00 Mu = 0.83 M = 407.49 _chemical_formula_sum 'C26 H23 N4 O1' _chemical_formula_moiety 'C26 H23 N4 O1' _chemical_compound_source ? _chemical_formula_weight 407.49 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_min 0.16 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_max 0.49 _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 0.083 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.99 # 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 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 17701 _reflns_number_total 6159 _diffrn_reflns_av_R_equivalents 0.096 # Number of reflections with Friedels Law is 6159 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6189 _diffrn_reflns_theta_min 2.997 _diffrn_reflns_theta_max 30.474 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 29.560 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 42 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.26 _refine_diff_density_max 0.42 _refine_ls_number_reflns 3252 _refine_ls_number_restraints 0 _refine_ls_number_parameters 280 #_refine_ls_R_factor_ref 0.0508 _refine_ls_wR_factor_ref 0.0627 _refine_ls_goodness_of_fit_ref 1.0905 #_reflns_number_all 6149 _refine_ls_R_factor_all 0.0968 _refine_ls_wR_factor_all 0.0672 # 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 3252 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_gt 0.0627 _refine_ls_shift/su_max 0.000183 # 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: 2.88 1.38 2.40 ; #_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 #; #? #; # PROCESSING SUMMARY (IUCr Office Use Only): #_journal_date_recd_electronic ? #_journal_date_to_coeditor ? #_journal_date_from_coeditor ? #_journal_date_accepted ? #_journal_date_printers_first ? #_journal_date_printers_final ? #_journal_date_proofs_out ? #_journal_date_proofs_in ? #_journal_coeditor_name ? #_journal_coeditor_code ? #_journal_coeditor_notes ? #_journal_techeditor_code ? #_journal_techeditor_notes ? #_journal_coden_ASTM ? #_journal_name_full ? #_journal_year ? #_journal_volume ? #_journal_issue ? #_journal_page_first ? #_journal_page_last ? #_journal_suppl_publ_number ? #_journal_suppl_publ_pages ? # # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Blessing, SORTAV ( ) 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. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. 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 C1 C 0.4284(2) 0.27661(6) 0.56434(19) 0.0219 1.0000 Uani . . . . . . C2 C 0.4333(3) 0.32456(6) 0.5607(2) 0.0260 1.0000 Uani . . . . . . C3 C 0.3321(3) 0.34655(7) 0.4333(2) 0.0316 1.0000 Uani . . . . . . C4 C 0.2305(3) 0.32290(7) 0.3115(2) 0.0339 1.0000 Uani . . . . . . C5 C 0.2247(3) 0.27619(7) 0.3139(2) 0.0296 1.0000 Uani . . . . . . C6 C 0.3219(3) 0.25251(6) 0.43946(19) 0.0240 1.0000 Uani . . . . . . C7 C 0.3169(3) 0.20451(6) 0.4469(2) 0.0245 1.0000 Uani . . . . . . C8 C 0.4110(2) 0.18184(6) 0.56986(18) 0.0217 1.0000 Uani . . . . . . C9 C 0.5220(2) 0.20532(6) 0.69733(18) 0.0199 1.0000 Uani . . . . . . C10 C 0.5296(2) 0.25321(6) 0.69343(18) 0.0208 1.0000 Uani . . . . . . C11 C 0.6345(3) 0.27776(6) 0.8179(2) 0.0236 1.0000 Uani . . . . . . C12 C 0.6393(3) 0.32604(6) 0.8098(2) 0.0282 1.0000 Uani . . . . . . C13 C 0.5447(3) 0.34807(6) 0.6879(2) 0.0292 1.0000 Uani . . . . . . C14 C 0.7308(3) 0.25472(6) 0.9441(2) 0.0267 1.0000 Uani . . . . . . C15 C 0.7232(3) 0.20818(6) 0.94931(19) 0.0253 1.0000 Uani . . . . . . C16 C 0.6203(2) 0.18401(6) 0.82763(19) 0.0215 1.0000 Uani . . . . . . C17 C 0.6690(2) 0.10461(6) 0.76552(18) 0.0217 1.0000 Uani . . . . . . C18 C 0.6434(2) 0.06355(6) 0.82152(19) 0.0213 1.0000 Uani . . . . . . C19 C 0.5685(3) 0.07426(6) 0.93286(19) 0.0241 1.0000 Uani . . . . . . C20 C 0.6968(2) 0.01900(6) 0.78936(17) 0.0195 1.0000 Uani . . . . . . C21 C 0.7435(3) -0.05596(6) 0.78847(19) 0.0222 1.0000 Uani . . . . . . C22 C 0.8687(3) -0.08767(7) 0.9031(2) 0.0348 1.0000 Uani . . . . . . C23 C 0.5546(3) -0.07939(7) 0.7058(2) 0.0307 1.0000 Uani . . . . . . C24 C 0.8490(3) -0.03531(6) 0.68892(18) 0.0219 1.0000 Uani . . . . . . C25 C 1.0678(3) -0.03158(7) 0.7589(2) 0.0306 1.0000 Uani . . . . . . C26 C 0.7989(3) -0.05585(7) 0.5402(2) 0.0296 1.0000 Uani . . . . . . N1 N 0.6129(2) 0.13627(5) 0.84127(15) 0.0221 1.0000 Uani . . . . . . N2 N 0.5517(2) 0.11803(5) 0.94652(16) 0.0243 1.0000 Uani . . . . . . N3 N 0.7708(2) 0.01129(5) 0.67752(16) 0.0220 1.0000 Uani . . . . . . N4 N 0.6877(2) -0.01688(5) 0.86021(16) 0.0232 1.0000 Uani . . . . . . O1 O 0.7996(2) 0.04114(5) 0.59435(15) 0.0314 1.0000 Uani . . . . . . H31 H 0.3327 0.3784 0.4306 0.0397 1.0000 Uiso R . . . . . H41 H 0.1646 0.3386 0.2255 0.0438 1.0000 Uiso R . . . . . H51 H 0.1543 0.2601 0.2297 0.0401 1.0000 Uiso R . . . . . H71 H 0.2460 0.1881 0.3636 0.0349 1.0000 Uiso R . . . . . H81 H 0.4029 0.1500 0.5717 0.0293 1.0000 Uiso R . . . . . H121 H 0.7109 0.3426 0.8924 0.0382 1.0000 Uiso R . . . . . H131 H 0.5519 0.3799 0.6857 0.0380 1.0000 Uiso R . . . . . H141 H 0.8019 0.2711 1.0273 0.0357 1.0000 Uiso R . . . . . H151 H 0.7878 0.1928 1.0362 0.0342 1.0000 Uiso R . . . . . H171 H 0.7165 0.1096 0.6881 0.0288 1.0000 Uiso R . . . . . H191 H 0.5339 0.0525 0.9903 0.0330 1.0000 Uiso R . . . . . H221 H 0.9867 -0.0732 0.9549 0.0460 1.0000 Uiso R . . . . . H222 H 0.8016 -0.0956 0.9671 0.0460 1.0000 Uiso R . . . . . H223 H 0.8954 -0.1140 0.8586 0.0460 1.0000 Uiso R . . . . . H231 H 0.4767 -0.0597 0.6344 0.0423 1.0000 Uiso R . . . . . H232 H 0.4878 -0.0873 0.7700 0.0423 1.0000 Uiso R . . . . . H233 H 0.5816 -0.1057 0.6614 0.0423 1.0000 Uiso R . . . . . H251 H 1.1219 -0.0188 0.6926 0.0397 1.0000 Uiso R . . . . . H252 H 1.0963 -0.0130 0.8414 0.0397 1.0000 Uiso R . . . . . H253 H 1.1212 -0.0606 0.7861 0.0397 1.0000 Uiso R . . . . . H261 H 0.8699 -0.0411 0.4883 0.0401 1.0000 Uiso R . . . . . H262 H 0.8310 -0.0869 0.5487 0.0401 1.0000 Uiso R . . . . . H263 H 0.6643 -0.0525 0.4907 0.0401 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 C1 0.0222(8) 0.0199(7) 0.0273(8) 0.0024(6) 0.0131(7) 0.0002(6) C2 0.0249(8) 0.0216(8) 0.0368(10) 0.0032(7) 0.0177(8) 0.0030(6) C3 0.0334(10) 0.0249(9) 0.0433(11) 0.0111(8) 0.0217(9) 0.0073(7) C4 0.0386(11) 0.0303(10) 0.0373(11) 0.0144(8) 0.0184(9) 0.0130(8) C5 0.0318(9) 0.0326(9) 0.0262(9) 0.0059(8) 0.0120(8) 0.0054(8) C6 0.0244(8) 0.0259(8) 0.0243(8) 0.0022(7) 0.0117(7) 0.0030(6) C7 0.0271(8) 0.0239(8) 0.0225(8) -0.0030(7) 0.0083(7) -0.0004(6) C8 0.0234(8) 0.0191(7) 0.0232(8) -0.0012(6) 0.0085(6) -0.0012(6) C9 0.0196(7) 0.0202(7) 0.0214(8) -0.0008(6) 0.0086(6) -0.0004(6) C10 0.0205(8) 0.0207(7) 0.0239(8) -0.0006(6) 0.0107(6) -0.0005(6) C11 0.0229(8) 0.0212(8) 0.0290(9) -0.0049(7) 0.0115(7) -0.0006(6) C12 0.0286(9) 0.0214(8) 0.0386(10) -0.0109(7) 0.0166(8) -0.0033(7) C13 0.0297(9) 0.0174(7) 0.0470(12) -0.0027(7) 0.0217(9) 0.0000(7) C14 0.0257(8) 0.0279(9) 0.0254(8) -0.0084(7) 0.0069(7) -0.0041(7) C15 0.0273(9) 0.0253(9) 0.0216(8) -0.0001(7) 0.0061(7) 0.0022(7) C16 0.0241(8) 0.0173(7) 0.0250(8) -0.0001(6) 0.0106(6) 0.0000(6) C17 0.0235(8) 0.0210(7) 0.0214(8) 0.0009(6) 0.0082(6) 0.0013(6) C18 0.0197(8) 0.0215(8) 0.0213(8) 0.0018(6) 0.0051(6) 0.0016(6) C19 0.0262(8) 0.0238(8) 0.0227(8) 0.0031(7) 0.0085(7) 0.0021(7) C20 0.0188(7) 0.0224(7) 0.0162(7) 0.0019(6) 0.0042(6) 0.0009(6) C21 0.0261(8) 0.0179(7) 0.0227(8) 0.0020(6) 0.0081(7) 0.0012(6) C22 0.0386(10) 0.0323(10) 0.0341(11) 0.0166(8) 0.0130(8) 0.0096(8) C23 0.0305(9) 0.0278(9) 0.0358(10) -0.0081(8) 0.0136(8) -0.0065(7) C24 0.0244(8) 0.0189(7) 0.0226(8) 0.0011(6) 0.0080(6) 0.0024(6) C25 0.0247(9) 0.0350(10) 0.0322(10) 0.0038(8) 0.0095(8) 0.0023(7) C26 0.0385(10) 0.0290(9) 0.0234(8) -0.0026(7) 0.0129(8) 0.0003(8) N1 0.0262(7) 0.0203(7) 0.0206(7) 0.0019(5) 0.0088(6) 0.0017(5) N2 0.0300(7) 0.0237(7) 0.0210(7) 0.0028(6) 0.0108(6) 0.0030(6) N3 0.0252(7) 0.0204(7) 0.0213(7) 0.0032(5) 0.0091(6) 0.0031(6) N4 0.0293(8) 0.0196(6) 0.0220(7) 0.0005(5) 0.0105(6) 0.0003(6) O1 0.0448(8) 0.0266(7) 0.0292(7) 0.0091(6) 0.0210(6) 0.0045(6) _refine_ls_extinction_method None 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 C1 . C2 . 1.429(2) yes C1 . C6 . 1.418(3) yes C1 . C10 . 1.427(2) yes C2 . C3 . 1.395(3) yes C2 . C13 . 1.435(3) yes C3 . C4 . 1.381(3) yes C3 . H31 . 0.950 no C4 . C5 . 1.392(3) yes C4 . H41 . 0.950 no C5 . C6 . 1.400(3) yes C5 . H51 . 0.950 no C6 . C7 . 1.433(3) yes C7 . C8 . 1.362(2) yes C7 . H71 . 0.950 no C8 . C9 . 1.435(2) yes C8 . H81 . 0.950 no C9 . C10 . 1.428(2) yes C9 . C16 . 1.402(2) yes C10 . C11 . 1.419(2) yes C11 . C12 . 1.441(2) yes C11 . C14 . 1.393(3) yes C12 . C13 . 1.345(3) yes C12 . H121 . 0.950 no C13 . H131 . 0.950 no C14 . C15 . 1.389(3) yes C14 . H141 . 0.950 no C15 . C16 . 1.390(2) yes C15 . H151 . 0.950 no C16 . N1 . 1.431(2) yes C17 . C18 . 1.380(2) yes C17 . N1 . 1.350(2) yes C17 . H171 . 0.950 no C18 . C19 . 1.418(2) yes C18 . C20 . 1.448(2) yes C19 . N2 . 1.320(2) yes C19 . H191 . 0.950 no C20 . N3 . 1.401(2) yes C20 . N4 . 1.291(2) yes C21 . C22 . 1.526(2) yes C21 . C23 . 1.524(3) yes C21 . C24 . 1.563(2) yes C21 . N4 . 1.489(2) yes C22 . H221 . 0.950 no C22 . H222 . 0.950 no C22 . H223 . 0.950 no C23 . H231 . 0.950 no C23 . H232 . 0.950 no C23 . H233 . 0.950 no C24 . C25 . 1.525(3) yes C24 . C26 . 1.520(2) yes C24 . N3 . 1.492(2) yes C25 . H251 . 0.950 no C25 . H252 . 0.950 no C25 . H253 . 0.950 no C26 . H261 . 0.950 no C26 . H262 . 0.950 no C26 . H263 . 0.950 no N1 . N2 . 1.373(2) yes N3 . O1 . 1.2746(19) 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 C2 . C1 . C6 . 119.68(17) yes C2 . C1 . C10 . 120.04(16) yes C6 . C1 . C10 . 120.29(16) yes C1 . C2 . C3 . 118.80(18) yes C1 . C2 . C13 . 118.52(17) yes C3 . C2 . C13 . 122.67(18) yes C2 . C3 . C4 . 121.29(18) yes C2 . C3 . H31 . 119.3 no C4 . C3 . H31 . 119.4 no C3 . C4 . C5 . 120.37(19) yes C3 . C4 . H41 . 119.7 no C5 . C4 . H41 . 119.9 no C4 . C5 . C6 . 120.60(19) yes C4 . C5 . H51 . 119.9 no C6 . C5 . H51 . 119.5 no C1 . C6 . C5 . 119.25(17) yes C1 . C6 . C7 . 118.48(16) yes C5 . C6 . C7 . 122.27(18) yes C6 . C7 . C8 . 121.77(17) yes C6 . C7 . H71 . 119.0 no C8 . C7 . H71 . 119.2 no C7 . C8 . C9 . 120.95(16) yes C7 . C8 . H81 . 119.7 no C9 . C8 . H81 . 119.3 no C8 . C9 . C10 . 118.61(16) yes C8 . C9 . C16 . 123.72(16) yes C10 . C9 . C16 . 117.64(15) yes C9 . C10 . C1 . 119.89(16) yes C9 . C10 . C11 . 120.40(16) yes C1 . C10 . C11 . 119.71(16) yes C10 . C11 . C12 . 118.80(17) yes C10 . C11 . C14 . 119.40(17) yes C12 . C11 . C14 . 121.80(17) yes C11 . C12 . C13 . 121.48(18) yes C11 . C12 . H121 . 119.2 no C13 . C12 . H121 . 119.3 no C2 . C13 . C12 . 121.44(17) yes C2 . C13 . H131 . 119.1 no C12 . C13 . H131 . 119.4 no C11 . C14 . C15 . 120.65(17) yes C11 . C14 . H141 . 119.4 no C15 . C14 . H141 . 119.9 no C14 . C15 . C16 . 120.13(17) yes C14 . C15 . H151 . 120.1 no C16 . C15 . H151 . 119.8 no C9 . C16 . C15 . 121.77(16) yes C9 . C16 . N1 . 120.82(16) yes C15 . C16 . N1 . 117.38(16) yes C18 . C17 . N1 . 106.87(15) yes C18 . C17 . H171 . 126.5 no N1 . C17 . H171 . 126.6 no C17 . C18 . C19 . 104.48(15) yes C17 . C18 . C20 . 129.91(16) yes C19 . C18 . C20 . 125.32(15) yes C18 . C19 . N2 . 111.99(16) yes C18 . C19 . H191 . 123.9 no N2 . C19 . H191 . 124.1 no C18 . C20 . N3 . 121.75(14) yes C18 . C20 . N4 . 125.00(15) yes N3 . C20 . N4 . 113.23(15) yes C22 . C21 . C23 . 109.32(16) yes C22 . C21 . C24 . 114.17(15) yes C23 . C21 . C24 . 113.15(15) yes C22 . C21 . N4 . 108.84(15) yes C23 . C21 . N4 . 105.64(15) yes C24 . C21 . N4 . 105.21(13) yes C21 . C22 . H221 . 109.6 no C21 . C22 . H222 . 109.4 no H221 . C22 . H222 . 109.5 no C21 . C22 . H223 . 109.4 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no C21 . C23 . H231 . 109.3 no C21 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no C21 . C23 . H233 . 109.6 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no C21 . C24 . C25 . 114.04(15) yes C21 . C24 . C26 . 115.94(15) yes C25 . C24 . C26 . 110.46(16) yes C21 . C24 . N3 . 98.99(13) yes C25 . C24 . N3 . 106.64(14) yes C26 . C24 . N3 . 109.71(15) yes C24 . C25 . H251 . 109.4 no C24 . C25 . H252 . 109.4 no H251 . C25 . H252 . 109.5 no C24 . C25 . H253 . 109.6 no H251 . C25 . H253 . 109.5 no H252 . C25 . H253 . 109.5 no C24 . C26 . H261 . 109.5 no C24 . C26 . H262 . 109.4 no H261 . C26 . H262 . 109.5 no C24 . C26 . H263 . 109.4 no H261 . C26 . H263 . 109.5 no H262 . C26 . H263 . 109.5 no C16 . N1 . C17 . 127.89(15) yes C16 . N1 . N2 . 119.77(14) yes C17 . N1 . N2 . 112.26(14) yes N1 . N2 . C19 . 104.38(14) yes C24 . N3 . C20 . 109.39(13) yes C24 . N3 . O1 . 123.82(14) yes C20 . N3 . O1 . 125.69(14) yes C21 . N4 . C20 . 108.53(14) yes # Attachment '4559_web_deposit_cif_file_4_YuliaBorozdina_1299676307.cif' data_baumyul1 _database_code_depnum_ccdc_archive 'CCDC 816634' #TrackingRef '4559_web_deposit_cif_file_4_YuliaBorozdina_1299676307.cif' _audit_creation_date 09-07-09 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.4598(2) _cell_length_b 29.3972(9) _cell_length_c 10.0132(3) _cell_angle_alpha 90 _cell_angle_beta 109.8210(16) _cell_angle_gamma 90 _cell_volume 2065.78(11) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z 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' 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' 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' _cell_formula_units_Z 4 # Given Formula = C26 H23 N4 O2 # Dc = 1.36 Fooo = 892.00 Mu = 0.88 M = 423.49 # Found Formula = C26 H23 N4 O2 # Dc = 1.36 FOOO = 892.00 Mu = 0.88 M = 423.49 _chemical_formula_sum 'C26 H23 N4 O2' _chemical_formula_moiety 'C26 H23 N4 O2' _chemical_compound_source ? _chemical_formula_weight 423.49 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour darkred _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 0.088 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.99 # 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 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 16040 _reflns_number_total 5785 _diffrn_reflns_av_R_equivalents 0.052 # Number of reflections with Friedels Law is 5785 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6038 _diffrn_reflns_theta_min 2.984 _diffrn_reflns_theta_max 30.023 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 27.621 _diffrn_measured_fraction_theta_full 0.961 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 41 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _refine_diff_density_max 0.54 _refine_ls_number_reflns 4027 _refine_ls_number_restraints 0 _refine_ls_number_parameters 289 #_refine_ls_R_factor_ref 0.0447 _refine_ls_wR_factor_ref 0.0561 _refine_ls_goodness_of_fit_ref 1.0804 #_reflns_number_all 5776 _refine_ls_R_factor_all 0.0651 _refine_ls_wR_factor_all 0.0589 # 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 4027 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_gt 0.0561 _refine_ls_shift/su_max 0.005256 # 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: 2.11 1.01 1.66 ; #_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 #; #? #; # PROCESSING SUMMARY (IUCr Office Use Only): #_journal_date_recd_electronic ? #_journal_date_to_coeditor ? #_journal_date_from_coeditor ? #_journal_date_accepted ? #_journal_date_printers_first ? #_journal_date_printers_final ? #_journal_date_proofs_out ? #_journal_date_proofs_in ? #_journal_coeditor_name ? #_journal_coeditor_code ? #_journal_coeditor_notes ? #_journal_techeditor_code ? #_journal_techeditor_notes ? #_journal_coden_ASTM ? #_journal_name_full ? #_journal_year ? #_journal_volume ? #_journal_issue ? #_journal_page_first ? #_journal_page_last ? #_journal_suppl_publ_number ? #_journal_suppl_publ_pages ? # # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Blessing, SORTAV ( ) 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. Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. 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 O1 O 0.28060(14) 0.03921(3) 0.57877(9) 0.0246 1.0000 Uani . . . . . . N3 N 0.26860(14) 0.00934(3) 0.66915(10) 0.0182 1.0000 Uani . . . . . . O2 O 0.21731(15) -0.02482(3) 0.98210(10) 0.0265 1.0000 Uani . . . . . . N4 N 0.23887(14) -0.02096(3) 0.86125(10) 0.0188 1.0000 Uani . . . . . . C14 C 0.07780(16) 0.20634(4) 0.71705(12) 0.0176 1.0000 Uani . . . . . . C16 C -0.01750(17) 0.27878(4) 0.58746(13) 0.0195 1.0000 Uani . . . . . . N1 N 0.17007(14) 0.13614(3) 0.85797(10) 0.0187 1.0000 Uani . . . . . . C13 C -0.03522(17) 0.18275(4) 0.59097(12) 0.0202 1.0000 Uani . . . . . . C15 C 0.08579(16) 0.25488(4) 0.71424(12) 0.0180 1.0000 Uani . . . . . . C4 C 0.19217(17) 0.27950(4) 0.83727(13) 0.0203 1.0000 Uani . . . . . . N2 N 0.11121(15) 0.11752(4) 0.96160(11) 0.0207 1.0000 Uani . . . . . . C21 C 0.32959(16) -0.03915(4) 0.66433(12) 0.0180 1.0000 Uani . . . . . . C11 C -0.12468(17) 0.25450(4) 0.46349(13) 0.0214 1.0000 Uani . . . . . . C1 C 0.17745(16) 0.18448(4) 0.84594(12) 0.0188 1.0000 Uani . . . . . . C20 C 0.23030(16) 0.01819(4) 0.78832(12) 0.0173 1.0000 Uani . . . . . . C24 C 0.24999(16) -0.06159(4) 0.77394(12) 0.0181 1.0000 Uani . . . . . . C10 C -0.2228(2) 0.27879(5) 0.33952(14) 0.0272 1.0000 Uani . . . . . . C23 C 0.54752(17) -0.03829(5) 0.71279(14) 0.0228 1.0000 Uani . . . . . . C2 C 0.28122(18) 0.20885(5) 0.96656(13) 0.0231 1.0000 Uani . . . . . . C8 C -0.1186(2) 0.35006(5) 0.46006(16) 0.0291 1.0000 Uani . . . . . . C7 C -0.01387(18) 0.32728(4) 0.58525(15) 0.0235 1.0000 Uani . . . . . . C19 C 0.12260(17) 0.07303(4) 0.94600(12) 0.0199 1.0000 Uani . . . . . . C6 C 0.09915(19) 0.35097(4) 0.71083(15) 0.0266 1.0000 Uani . . . . . . C17 C 0.21793(16) 0.10399(4) 0.77926(12) 0.0189 1.0000 Uani . . . . . . C22 C 0.24439(19) -0.05767(4) 0.51401(13) 0.0243 1.0000 Uani . . . . . . C5 C 0.19764(19) 0.32833(4) 0.82996(15) 0.0254 1.0000 Uani . . . . . . C3 C 0.28924(18) 0.25585(5) 0.96242(14) 0.0242 1.0000 Uani . . . . . . C25 C 0.04605(18) -0.07956(5) 0.70991(14) 0.0247 1.0000 Uani . . . . . . C26 C 0.37748(19) -0.09768(5) 0.86745(14) 0.0256 1.0000 Uani . . . . . . C12 C -0.13058(18) 0.20588(5) 0.47010(13) 0.0227 1.0000 Uani . . . . . . C18 C 0.19085(16) 0.06228(4) 0.83366(12) 0.0178 1.0000 Uani . . . . . . C9 C -0.2193(2) 0.32601(5) 0.33810(16) 0.0314 1.0000 Uani . . . . . . H131 H -0.0437 0.1505 0.5921 0.0272 1.0000 Uiso R . . . . . H101 H -0.2928 0.2627 0.2559 0.0363 1.0000 Uiso R . . . . . H231 H 0.5938 -0.0683 0.7117 0.0303 1.0000 Uiso R . . . . . H232 H 0.5971 -0.0263 0.8063 0.0303 1.0000 Uiso R . . . . . H233 H 0.5867 -0.0197 0.6502 0.0303 1.0000 Uiso R . . . . . H21 H 0.3463 0.1931 1.0522 0.0308 1.0000 Uiso R . . . . . H81 H -0.1204 0.3824 0.4586 0.0369 1.0000 Uiso R . . . . . H191 H 0.0895 0.0510 1.0031 0.0264 1.0000 Uiso R . . . . . H61 H 0.1034 0.3833 0.7098 0.0339 1.0000 Uiso R . . . . . H171 H 0.2614 0.1090 0.7016 0.0256 1.0000 Uiso R . . . . . H221 H 0.2836 -0.0883 0.5120 0.0316 1.0000 Uiso R . . . . . H222 H 0.1093 -0.0564 0.4848 0.0316 1.0000 Uiso R . . . . . H223 H 0.2872 -0.0399 0.4515 0.0316 1.0000 Uiso R . . . . . H51 H 0.2732 0.3449 0.9110 0.0329 1.0000 Uiso R . . . . . H31 H 0.3621 0.2722 1.0448 0.0320 1.0000 Uiso R . . . . . H251 H 0.0448 -0.1055 0.6532 0.0329 1.0000 Uiso R . . . . . H252 H -0.0006 -0.0877 0.7839 0.0329 1.0000 Uiso R . . . . . H253 H -0.0327 -0.0566 0.6527 0.0329 1.0000 Uiso R . . . . . H261 H 0.3838 -0.1233 0.8113 0.0341 1.0000 Uiso R . . . . . H262 H 0.3267 -0.1067 0.9385 0.0341 1.0000 Uiso R . . . . . H263 H 0.5017 -0.0856 0.9113 0.0341 1.0000 Uiso R . . . . . H121 H -0.2029 0.1895 0.3876 0.0311 1.0000 Uiso R . . . . . H91 H -0.2861 0.3419 0.2532 0.0406 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 O1 0.0359(5) 0.0196(4) 0.0218(4) 0.0062(3) 0.0144(4) 0.0029(4) N3 0.0221(5) 0.0159(4) 0.0174(4) 0.0015(3) 0.0079(4) 0.0005(3) O2 0.0390(5) 0.0250(5) 0.0206(4) 0.0012(3) 0.0169(4) -0.0028(4) N4 0.0225(5) 0.0171(5) 0.0179(4) 0.0010(3) 0.0083(4) -0.0019(3) C14 0.0184(5) 0.0160(5) 0.0210(5) -0.0008(4) 0.0102(4) -0.0003(4) C16 0.0205(5) 0.0165(5) 0.0260(6) 0.0016(4) 0.0139(4) 0.0013(4) N1 0.0198(4) 0.0181(5) 0.0196(4) 0.0012(3) 0.0086(4) 0.0011(4) C13 0.0217(5) 0.0170(5) 0.0221(5) -0.0018(4) 0.0077(4) -0.0015(4) C15 0.0177(5) 0.0160(5) 0.0232(5) -0.0013(4) 0.0108(4) 0.0001(4) C4 0.0203(5) 0.0164(5) 0.0279(6) -0.0042(4) 0.0131(5) -0.0019(4) N2 0.0230(5) 0.0217(5) 0.0197(4) 0.0020(4) 0.0101(4) 0.0021(4) C21 0.0208(5) 0.0160(5) 0.0174(5) 0.0007(4) 0.0069(4) 0.0016(4) C11 0.0226(5) 0.0201(6) 0.0240(6) 0.0031(4) 0.0113(5) 0.0024(4) C1 0.0196(5) 0.0166(5) 0.0221(5) -0.0007(4) 0.0095(4) 0.0006(4) C20 0.0190(5) 0.0159(5) 0.0172(5) 0.0010(4) 0.0063(4) -0.0014(4) C24 0.0207(5) 0.0154(5) 0.0187(5) -0.0003(4) 0.0073(4) -0.0017(4) C10 0.0292(6) 0.0292(7) 0.0249(6) 0.0054(5) 0.0114(5) 0.0056(5) C23 0.0205(5) 0.0231(6) 0.0265(6) 0.0003(4) 0.0101(4) -0.0004(4) C2 0.0227(5) 0.0233(6) 0.0222(5) -0.0026(4) 0.0064(4) 0.0013(4) C8 0.0320(6) 0.0210(6) 0.0424(7) 0.0102(5) 0.0232(6) 0.0067(5) C7 0.0248(6) 0.0169(5) 0.0361(7) 0.0032(4) 0.0197(5) 0.0020(4) C19 0.0206(5) 0.0218(6) 0.0191(5) 0.0018(4) 0.0091(4) 0.0002(4) C6 0.0285(6) 0.0163(5) 0.0434(7) -0.0037(5) 0.0230(6) -0.0024(5) C17 0.0203(5) 0.0178(5) 0.0202(5) 0.0001(4) 0.0089(4) 0.0011(4) C22 0.0296(6) 0.0234(6) 0.0198(5) -0.0028(4) 0.0082(5) -0.0019(5) C5 0.0260(6) 0.0182(6) 0.0388(7) -0.0091(5) 0.0199(5) -0.0044(4) C3 0.0238(5) 0.0245(6) 0.0248(6) -0.0065(4) 0.0088(5) -0.0015(4) C25 0.0227(5) 0.0243(6) 0.0274(6) -0.0015(5) 0.0089(5) -0.0055(4) C26 0.0285(6) 0.0216(6) 0.0266(6) 0.0065(4) 0.0092(5) 0.0025(5) C12 0.0236(5) 0.0225(6) 0.0218(5) -0.0007(4) 0.0075(4) -0.0002(4) C18 0.0174(5) 0.0186(5) 0.0176(5) 0.0005(4) 0.0063(4) 0.0002(4) C9 0.0343(7) 0.0312(7) 0.0342(7) 0.0130(5) 0.0187(6) 0.0104(5) _refine_ls_extinction_method None 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 O1 . N3 . 1.2857(13) yes N3 . C21 . 1.5021(15) yes N3 . C20 . 1.3433(15) yes O2 . N4 . 1.2786(13) yes N4 . C20 . 1.3531(14) yes N4 . C24 . 1.4989(15) yes C14 . C13 . 1.4364(16) yes C14 . C15 . 1.4290(16) yes C14 . C1 . 1.4072(16) yes C16 . C15 . 1.4268(16) yes C16 . C11 . 1.4201(17) yes C16 . C7 . 1.4262(16) yes N1 . N2 . 1.3704(14) yes N1 . C1 . 1.4290(15) yes N1 . C17 . 1.3537(15) yes C13 . C12 . 1.3599(17) yes C13 . H131 . 0.950 no C15 . C4 . 1.4171(16) yes C4 . C5 . 1.4386(17) yes C4 . C3 . 1.4010(18) yes N2 . C19 . 1.3236(16) yes C21 . C24 . 1.5602(16) yes C21 . C23 . 1.5310(16) yes C21 . C22 . 1.5222(16) yes C11 . C10 . 1.4036(17) yes C11 . C12 . 1.4321(18) yes C1 . C2 . 1.3917(17) yes C20 . C18 . 1.4364(16) yes C24 . C25 . 1.5308(17) yes C24 . C26 . 1.5175(17) yes C10 . C9 . 1.389(2) yes C10 . H101 . 0.950 no C23 . H231 . 0.950 no C23 . H232 . 0.950 no C23 . H233 . 0.950 no C2 . C3 . 1.3842(19) yes C2 . H21 . 0.950 no C8 . C7 . 1.4022(19) yes C8 . C9 . 1.390(2) yes C8 . H81 . 0.950 no C7 . C6 . 1.4346(19) yes C19 . C18 . 1.4187(16) yes C19 . H191 . 0.950 no C6 . C5 . 1.346(2) yes C6 . H61 . 0.950 no C17 . C18 . 1.3839(16) yes C17 . H171 . 0.950 no C22 . H221 . 0.950 no C22 . H222 . 0.950 no C22 . H223 . 0.950 no C5 . H51 . 0.950 no C3 . H31 . 0.950 no C25 . H251 . 0.950 no C25 . H252 . 0.950 no C25 . H253 . 0.950 no C26 . H261 . 0.950 no C26 . H262 . 0.950 no C26 . H263 . 0.950 no C12 . H121 . 0.950 no C9 . H91 . 0.950 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 O1 . N3 . C21 . 122.10(9) yes O1 . N3 . C20 . 125.41(10) yes C21 . N3 . C20 . 111.74(9) yes O2 . N4 . C20 . 126.02(10) yes O2 . N4 . C24 . 122.07(9) yes C20 . N4 . C24 . 111.40(9) yes C13 . C14 . C15 . 118.73(10) yes C13 . C14 . C1 . 123.77(11) yes C15 . C14 . C1 . 117.47(10) yes C15 . C16 . C11 . 120.29(11) yes C15 . C16 . C7 . 119.92(11) yes C11 . C16 . C7 . 119.80(11) yes N2 . N1 . C1 . 119.49(10) yes N2 . N1 . C17 . 112.18(10) yes C1 . N1 . C17 . 128.32(10) yes C14 . C13 . C12 . 120.99(12) yes C14 . C13 . H131 . 119.5 no C12 . C13 . H131 . 119.5 no C14 . C15 . C16 . 119.72(10) yes C14 . C15 . C4 . 120.51(11) yes C16 . C15 . C4 . 119.75(11) yes C15 . C4 . C5 . 118.86(12) yes C15 . C4 . C3 . 119.43(11) yes C5 . C4 . C3 . 121.72(12) yes N1 . N2 . C19 . 104.79(9) yes N3 . C21 . C24 . 100.77(8) yes N3 . C21 . C23 . 105.95(10) yes C24 . C21 . C23 . 113.61(9) yes N3 . C21 . C22 . 109.97(9) yes C24 . C21 . C22 . 114.43(10) yes C23 . C21 . C22 . 111.21(10) yes C16 . C11 . C10 . 119.18(12) yes C16 . C11 . C12 . 118.57(11) yes C10 . C11 . C12 . 122.25(12) yes N1 . C1 . C14 . 120.52(10) yes N1 . C1 . C2 . 117.69(10) yes C14 . C1 . C2 . 121.76(11) yes N4 . C20 . N3 . 109.22(10) yes N4 . C20 . C18 . 125.05(10) yes N3 . C20 . C18 . 125.71(10) yes C21 . C24 . N4 . 100.55(9) yes C21 . C24 . C25 . 114.37(10) yes N4 . C24 . C25 . 106.00(9) yes C21 . C24 . C26 . 114.91(10) yes N4 . C24 . C26 . 110.13(10) yes C25 . C24 . C26 . 110.06(10) yes C11 . C10 . C9 . 120.77(13) yes C11 . C10 . H101 . 119.5 no C9 . C10 . H101 . 119.8 no C21 . C23 . H231 . 109.4 no C21 . C23 . H232 . 109.6 no H231 . C23 . H232 . 109.5 no C21 . C23 . H233 . 109.4 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no C1 . C2 . C3 . 120.31(12) yes C1 . C2 . H21 . 119.7 no C3 . C2 . H21 . 120.0 no C7 . C8 . C9 . 120.91(13) yes C7 . C8 . H81 . 119.5 no C9 . C8 . H81 . 119.6 no C16 . C7 . C8 . 118.91(13) yes C16 . C7 . C6 . 118.71(12) yes C8 . C7 . C6 . 122.37(12) yes N2 . C19 . C18 . 111.61(10) yes N2 . C19 . H191 . 124.2 no C18 . C19 . H191 . 124.2 no C7 . C6 . C5 . 121.25(12) yes C7 . C6 . H61 . 119.2 no C5 . C6 . H61 . 119.6 no N1 . C17 . C18 . 106.67(10) yes N1 . C17 . H171 . 126.7 no C18 . C17 . H171 . 126.6 no C21 . C22 . H221 . 109.4 no C21 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C21 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no C4 . C5 . C6 . 121.47(12) yes C4 . C5 . H51 . 119.1 no C6 . C5 . H51 . 119.4 no C4 . C3 . C2 . 120.51(11) yes C4 . C3 . H31 . 119.7 no C2 . C3 . H31 . 119.8 no C24 . C25 . H251 . 109.6 no C24 . C25 . H252 . 109.6 no H251 . C25 . H252 . 109.5 no C24 . C25 . H253 . 109.3 no H251 . C25 . H253 . 109.5 no H252 . C25 . H253 . 109.5 no C24 . C26 . H261 . 109.6 no C24 . C26 . H262 . 109.4 no H261 . C26 . H262 . 109.5 no C24 . C26 . H263 . 109.4 no H261 . C26 . H263 . 109.5 no H262 . C26 . H263 . 109.5 no C11 . C12 . C13 . 121.68(12) yes C11 . C12 . H121 . 118.9 no C13 . C12 . H121 . 119.4 no C20 . C18 . C19 . 128.21(11) yes C20 . C18 . C17 . 127.02(11) yes C19 . C18 . C17 . 104.74(10) yes C8 . C9 . C10 . 120.38(13) yes C8 . C9 . H91 . 119.9 no C10 . C9 . H91 . 119.7 no