# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Gunther Brunklaus' _publ_contact_author_email BRUNKLAUS@MPIP-MAINZ.MPG.DE _publ_section_title ; PROBING ATOMIC LEVEL STRUCTURAL TRANSFORMATION IN O-H---N HETEROSYNTHON CRYSTAL ; _publ_contact_author_address ; Max-Planck-Institute for Polymer Research Ackermannweg 10 D-55021 Mainz Germany ; _publ_contact_author_fax '+49 379100' _publ_contact_author_phone '+49 379133' loop_ _publ_author_name 'Gunther Brunklaus' 'Volker Enkelmann' 'Mujeeb Khan' # Attachment 'khan14.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 710270' _audit_creation_date 09-01-15 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'Khan_x1 teilumgesetzt 120K 06-07' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.9360(4) _cell_length_b 9.8340(5) _cell_length_c 10.9160(5) _cell_angle_alpha 93.0700(12) _cell_angle_beta 106.7800(13) _cell_angle_gamma 113.5611(13) _cell_volume 733.66(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? 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' 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 2 # Given Formula = C18 H16 N2 O2 # Dc = 1.32 Fooo = 308.00 Mu = 0.88 M = 292.34 # Found Formula = C18 H16 N2 O2 # Dc = 1.32 FOOO = 308.00 Mu = 0.88 M = 292.34 _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_moiety 'C18 H16 N2 O2' _chemical_compound_source ? _chemical_formula_weight 292.34 _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 colourless _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.39 _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 308 _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 0.90 _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 12245 _reflns_number_total 3779 _diffrn_reflns_av_R_equivalents 0.045 # Number of reflections with Friedels Law is 3779 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3900 _diffrn_reflns_theta_min 4.079 _diffrn_reflns_theta_max 28.995 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.225 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _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 -0.30 _refine_diff_density_max 0.44 _refine_ls_number_reflns 2050 _refine_ls_number_restraints 5 _refine_ls_number_parameters 194 #_refine_ls_R_factor_ref 0.0672 _refine_ls_wR_factor_ref 0.0214 _refine_ls_goodness_of_fit_ref 1.1864 #_reflns_number_all 3779 _refine_ls_R_factor_all 0.1338 _refine_ls_wR_factor_all 0.0346 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2050 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_gt 0.0214 _refine_ls_shift/su_max 0.016796 # 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: 2.73 -8.79 0.158 ; #_publ_section_title # Title of paper - generally just the systematic or trivial name #; ? #; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. #loop_ # _publ_author_name # _publ_author_address # _publ_author_footnote # 'Other, Anthony N.' # Author 1 #; # ? # Address for author 1 #; #; # ? # Footnote for author 1 #; # 'Else, S. O.' # Author 2 #; # ? # Address 2 #; #; # ? # Footnote 2 #; #_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 N11 N 0.2459(3) 0.75539(19) 0.43254(17) 0.0374 1.0000 Uani . . . . . . N12 N 0.3265(2) 0.34793(18) -0.33493(17) 0.0337 1.0000 Uani . . . . . . C1 C -0.1477(3) 0.8088(2) 0.6601(2) 0.0299 1.0000 Uani . . . . . . C3 C 0.1870(3) 0.84577(17) 0.72265(18) 0.0262 1.0000 Uani . . . . . . C13 C 0.2506(3) 0.6605(2) 0.18718(19) 0.0314 1.0000 Uani D . . . . . C18 C 0.2626(3) 0.4386(2) -0.1103(2) 0.0367 1.0000 Uani D . . . . . O1 O -0.32645(19) 0.76858(15) 0.56868(15) 0.0383 1.0000 Uani . . . . . . O2 O 0.34193(19) 0.84276(14) 0.69449(13) 0.0319 1.0000 Uani . . . . . . C2 C 0.0074(3) 0.80620(19) 0.62682(18) 0.0267 1.0000 Uani . . . . . . C4 C 0.2116(3) 0.8898(2) 0.85243(18) 0.0318 1.0000 Uani . . . . . . C5 C 0.0564(3) 0.8931(2) 0.8835(2) 0.0340 1.0000 Uani . . . . . . C6 C -0.1237(3) 0.8530(2) 0.7894(2) 0.0337 1.0000 Uani . . . . . . C11 C 0.1825(3) 0.6085(2) 0.3825(2) 0.0368 1.0000 Uani . . . . . . C12 C 0.1817(3) 0.5575(2) 0.26393(18) 0.0302 1.0000 Uani . . . . . . C14 C 0.3139(3) 0.81262(19) 0.23772(18) 0.0303 1.0000 Uani . . . . . . C15 C 0.3086(3) 0.8550(2) 0.3578(2) 0.0334 1.0000 Uani . . . . . . C19 C 0.2094(3) 0.2876(2) -0.1564(2) 0.0361 1.0000 Uani . . . . . . C20 C 0.2426(3) 0.2469(2) -0.2667(2) 0.0350 1.0000 Uani . . . . . . C21 C 0.3789(3) 0.4929(2) -0.2911(2) 0.0385 1.0000 Uani . . . . . . C22 C 0.3497(3) 0.5419(2) -0.18218(19) 0.0397 1.0000 Uani . . . . . . C16 C 0.2813(3) 0.6190(2) 0.0637(2) 0.0279 0.8529 Uani . . . . . . C17 C 0.2352(3) 0.4806(2) 0.0073(2) 0.0279 0.8529 Uani . . . . . . C26 C 0.1235(17) 0.6025(13) 0.0505(12) 0.0279 0.1471 Uani D . . . . . C27 C 0.1066(18) 0.4480(13) -0.0045(12) 0.0279 0.1471 Uani D . . . . . H21 H -0.0095 0.7768 0.5381 0.0342 1.0000 Uiso R . . . . . H41 H 0.3338 0.9170 0.9187 0.0392 1.0000 Uiso R . . . . . H51 H 0.0739 0.9240 0.9720 0.0425 1.0000 Uiso R . . . . . H61 H -0.2291 0.8557 0.8125 0.0417 1.0000 Uiso R . . . . . H111 H 0.1367 0.5363 0.4338 0.0458 1.0000 Uiso R . . . . . H121 H 0.1336 0.4522 0.2331 0.0395 1.0000 Uiso R . . . . . H141 H 0.3604 0.8866 0.1880 0.0410 1.0000 Uiso R . . . . . H151 H 0.3515 0.9593 0.3896 0.0432 1.0000 Uiso R . . . . . H191 H 0.1497 0.2122 -0.1118 0.0450 1.0000 Uiso R . . . . . H201 H 0.2065 0.1432 -0.2958 0.0446 1.0000 Uiso R . . . . . H211 H 0.4389 0.5651 -0.3379 0.0468 1.0000 Uiso R . . . . . H221 H 0.3899 0.6467 -0.1550 0.0482 1.0000 Uiso R . . . . . H161 H 0.3385 0.6985 0.0217 0.0367 0.8529 Uiso R . . . . . H171 H 0.1790 0.4018 0.0503 0.0367 0.8529 Uiso R . . . . . H261 H 0.1725 0.6751 0.0003 0.0367 0.1471 Uiso R . . . . . H271 H 0.1430 0.4050 0.0688 0.0367 0.1471 Uiso R . . . . . H1 H -0.3264 0.7283 0.4876 0.0497 1.0000 Uiso R . . . . . H2 H 0.3086 0.8124 0.6033 0.0437 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 N11 0.0459(10) 0.0387(9) 0.0368(10) 0.0135(8) 0.0221(9) 0.0211(8) N12 0.0249(8) 0.0321(9) 0.0334(10) 0.0072(7) -0.0003(7) 0.0088(7) C1 0.0353(11) 0.0200(10) 0.0354(12) 0.0082(9) 0.0137(10) 0.0114(8) C3 0.0303(11) 0.0140(9) 0.0301(11) 0.0073(8) 0.0101(9) 0.0051(7) C13 0.0346(12) 0.0263(10) 0.0272(11) 0.0073(8) 0.0053(9) 0.0107(8) C18 0.0477(13) 0.0253(10) 0.0249(11) 0.0029(8) -0.0019(10) 0.0140(9) O1 0.0303(8) 0.0426(9) 0.0412(9) 0.0089(7) 0.0121(7) 0.0151(6) O2 0.0301(7) 0.0296(7) 0.0329(8) 0.0102(6) 0.0110(6) 0.0093(6) C2 0.0316(10) 0.0198(9) 0.0227(9) 0.0062(7) 0.0078(8) 0.0060(7) C4 0.0409(12) 0.0203(9) 0.0247(11) 0.0054(7) 0.0058(9) 0.0076(8) C5 0.0559(14) 0.0220(10) 0.0245(10) 0.0064(8) 0.0173(9) 0.0144(9) C6 0.0453(13) 0.0240(10) 0.0417(12) 0.0096(9) 0.0258(11) 0.0166(9) C11 0.0391(12) 0.0331(11) 0.0442(13) 0.0180(10) 0.0203(10) 0.0160(9) C12 0.0288(10) 0.0264(10) 0.0317(11) 0.0093(9) 0.0062(8) 0.0107(8) C14 0.0314(10) 0.0230(9) 0.0308(11) 0.0086(8) 0.0070(9) 0.0085(8) C15 0.0293(10) 0.0275(9) 0.0418(12) 0.0067(9) 0.0119(9) 0.0110(8) C19 0.0376(12) 0.0232(10) 0.0350(11) 0.0065(8) 0.0044(9) 0.0062(8) C20 0.0305(10) 0.0251(10) 0.0392(13) 0.0063(9) 0.0032(9) 0.0082(8) C21 0.0332(12) 0.0332(11) 0.0347(12) 0.0102(9) -0.0015(9) 0.0089(9) C22 0.0430(13) 0.0223(9) 0.0386(13) 0.0085(9) -0.0005(10) 0.0090(9) C16 0.0337(4) 0.0249(4) 0.0257(4) 0.0111(4) 0.0120(4) 0.0112(4) C17 0.0337(4) 0.0249(4) 0.0257(4) 0.0111(4) 0.0120(4) 0.0112(4) C26 0.0337(4) 0.0249(4) 0.0257(4) 0.0111(4) 0.0120(4) 0.0112(4) C27 0.0337(4) 0.0249(4) 0.0257(4) 0.0111(4) 0.0120(4) 0.0112(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 5.095(8) 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 N11 . C11 . 1.347(3) yes N11 . C15 . 1.343(2) yes N12 . C20 . 1.350(2) yes N12 . C21 . 1.331(2) yes C1 . O1 . 1.363(2) yes C1 . C2 . 1.389(3) yes C1 . C6 . 1.390(3) yes C3 . O2 . 1.362(2) yes C3 . C2 . 1.389(2) yes C3 . C4 . 1.393(3) yes C13 . C12 . 1.393(2) yes C13 . C14 . 1.394(3) yes C13 . C16 . 1.501(3) yes C13 . C26 . 1.466(12) yes C18 . C19 . 1.390(3) yes C18 . C22 . 1.401(3) yes C18 . C17 . 1.429(3) yes O1 . H1 . 0.950 no O2 . H2 . 0.950 no C2 . H21 . 0.950 no C4 . C5 . 1.380(3) yes C4 . H41 . 0.950 no C5 . C6 . 1.382(3) yes C5 . H51 . 0.950 no C6 . H61 . 0.950 no C11 . C12 . 1.360(3) yes C11 . H111 . 0.950 no C12 . H121 . 0.950 no C14 . C15 . 1.372(3) yes C14 . H141 . 0.950 no C15 . H151 . 0.950 no C19 . C20 . 1.377(3) yes C19 . H191 . 0.950 no C20 . H201 . 0.950 no C21 . C22 . 1.373(3) yes C21 . H211 . 0.950 no C22 . H221 . 0.950 no C16 . C17 . 1.322(3) yes C16 . C26 . 1.160(12) yes C16 . C27 . 1.647(12) yes C16 . H161 . 0.950 no C16 . H261 . 1.267 no C17 . C27 . 0.904(12) yes C17 . H171 . 0.950 no C17 . H271 . 1.200 no C26 . C27 2_565 1.598(16) yes C26 . C27 . 1.543(17) yes C26 . H261 . 0.950 no C27 . H171 . 0.966 no C27 . H271 . 0.950 no H171 . H271 . 0.404 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 C11 . N11 . C15 . 116.60(18) yes C20 . N12 . C21 . 117.17(19) yes O1 . C1 . C2 . 121.77(19) yes O1 . C1 . C6 . 117.97(18) yes C2 . C1 . C6 . 120.27(19) yes O2 . C3 . C2 . 122.21(19) yes O2 . C3 . C4 . 118.16(17) yes C2 . C3 . C4 . 119.6(2) yes C12 . C13 . C14 . 116.61(19) yes C12 . C13 . C16 . 123.86(17) yes C14 . C13 . C16 . 119.12(18) yes C12 . C13 . C26 . 110.1(5) yes C14 . C13 . C26 . 117.8(5) yes C16 . C13 . C26 . 46.0(5) yes C19 . C18 . C22 . 116.0(2) yes C19 . C18 . C17 . 119.9(2) yes C22 . C18 . C17 . 124.09(18) yes C1 . O1 . H1 . 108.6 no C3 . O2 . H2 . 110.6 no C1 . C2 . C3 . 120.31(19) yes C1 . C2 . H21 . 119.9 no C3 . C2 . H21 . 119.8 no C3 . C4 . C5 . 119.25(19) yes C3 . C4 . H41 . 120.3 no C5 . C4 . H41 . 120.5 no C4 . C5 . C6 . 121.9(2) yes C4 . C5 . H51 . 119.1 no C6 . C5 . H51 . 119.1 no C1 . C6 . C5 . 118.7(2) yes C1 . C6 . H61 . 120.5 no C5 . C6 . H61 . 120.8 no N11 . C11 . C12 . 124.09(18) yes N11 . C11 . H111 . 117.7 no C12 . C11 . H111 . 118.2 no C13 . C12 . C11 . 119.56(17) yes C13 . C12 . H121 . 120.0 no C11 . C12 . H121 . 120.4 no C13 . C14 . C15 . 120.35(18) yes C13 . C14 . H141 . 119.4 no C15 . C14 . H141 . 120.3 no C14 . C15 . N11 . 122.76(18) yes C14 . C15 . H151 . 118.7 no N11 . C15 . H151 . 118.6 no C18 . C19 . C20 . 120.21(19) yes C18 . C19 . H191 . 120.0 no C20 . C19 . H191 . 119.8 no C19 . C20 . N12 . 123.03(18) yes C19 . C20 . H201 . 118.8 no N12 . C20 . H201 . 118.2 no N12 . C21 . C22 . 123.1(2) yes N12 . C21 . H211 . 118.0 no C22 . C21 . H211 . 119.0 no C18 . C22 . C21 . 120.53(19) yes C18 . C22 . H221 . 119.8 no C21 . C22 . H221 . 119.7 no C13 . C16 . C17 . 125.71(19) yes C13 . C16 . C26 . 65.4(6) yes C17 . C16 . C26 . 97.1(6) yes C13 . C16 . C27 . 105.6(5) yes C17 . C16 . C27 . 33.2(4) yes C26 . C16 . C27 . 64.0(7) yes C13 . C16 . H161 . 117.7 no C17 . C16 . H161 . 116.6 no C26 . C16 . H161 . 108.6 no C27 . C16 . H161 . 127.9 no C13 . C16 . H261 . 91.2 no C17 . C16 . H261 . 113.1 no C26 . C16 . H261 . 45.8 no C27 . C16 . H261 . 89.8 no H161 . C16 . H261 . 63.0 no C18 . C17 . C16 . 126.6(2) yes C18 . C17 . C27 . 110.8(8) yes C16 . C17 . C27 . 93.5(8) yes C18 . C17 . H171 . 117.3 no C16 . C17 . H171 . 116.1 no C27 . C17 . H171 . 62.7 no C18 . C17 . H271 . 130.7 no C16 . C17 . H271 . 101.9 no C27 . C17 . H271 . 51.4 no H171 . C17 . H271 . 17.1 no C27 2_565 C26 . C13 . 122.8(9) yes C27 2_565 C26 . C16 . 167.2(11) yes C13 . C26 . C16 . 68.6(6) yes C27 2_565 C26 . C27 . 95.3(10) yes C13 . C26 . C27 . 113.0(9) yes C16 . C26 . C27 . 73.5(8) yes C27 2_565 C26 . H261 . 106.0 no C13 . C26 . H261 . 108.5 no C16 . C26 . H261 . 73.0 no C27 . C26 . H261 . 110.3 no C26 . C27 . C26 2_565 84.7(10) yes C26 . C27 . C16 . 42.5(5) yes C26 2_565 C27 . C16 . 126.9(9) yes C26 . C27 . C17 . 95.6(10) yes C26 2_565 C27 . C17 . 169.9(12) yes C16 . C27 . C17 . 53.2(6) yes C26 . C27 . H171 . 119.6 no C26 2_565 C27 . H171 . 127.5 no C16 . C27 . H171 . 92.0 no C17 . C27 . H171 . 61.0 no C26 . C27 . H271 . 106.2 no C26 2_565 C27 . H271 . 109.1 no C16 . C27 . H271 . 94.1 no C17 . C27 . H271 . 80.6 no H171 . C27 . H271 . 24.3 no C27 . H171 . C17 . 56.3 no C27 . H171 . H271 . 75.7 no C17 . H171 . H271 . 119.2 no C26 . H261 . C16 . 61.1 no C17 . H271 . C27 . 48.0 no C17 . H271 . H171 . 43.7 no C27 . H271 . H171 . 80.0 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 O1 . H1 . N12 2_565 180 0.95 1.79 2.740(2) yes O2 . H2 . N11 . 180 0.95 1.78 2.730(2) yes # Attachment 'khan42.cif' data_CRYSTALS_cif2 _database_code_depnum_ccdc_archive 'CCDC 710271' _audit_creation_date 09-01-15 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'Khanx1 irrad 120K 02-07' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.7682(4) _cell_length_b 9.7938(5) _cell_length_c 11.0478(5) _cell_angle_alpha 94.4493(12) _cell_angle_beta 104.8507(13) _cell_angle_gamma 111.4950(13) _cell_volume 742.07(6) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? 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' 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 2 # Given Formula = C18 H16 N2 O2 # Dc = 1.31 Fooo = 308.00 Mu = 0.87 M = 292.34 # Found Formula = C18 H16 N2 O2 # Dc = 1.31 FOOO = 308.00 Mu = 0.87 M = 292.34 _chemical_formula_sum 'C18 H16 N2 O2' _chemical_formula_moiety 'C18 H16 N2 O2' _chemical_compound_source ? _chemical_formula_weight 292.34 _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 colourless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_max 0.33 _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.087 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.88 _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 13514 _reflns_number_total 3357 _diffrn_reflns_av_R_equivalents 0.067 # Number of reflections with Friedels Law is 3357 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3401 _diffrn_reflns_theta_min 4.101 _diffrn_reflns_theta_max 27.491 _diffrn_measured_fraction_theta_max 0.784 _diffrn_reflns_theta_full 25.017 _diffrn_measured_fraction_theta_full 0.823 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 9 _reflns_limit_k_min -12 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _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 -0.34 _refine_diff_density_max 0.29 _refine_ls_number_reflns 2100 _refine_ls_number_restraints 0 _refine_ls_number_parameters 217 #_refine_ls_R_factor_ref 0.0528 _refine_ls_wR_factor_ref 0.0561 _refine_ls_goodness_of_fit_ref 0.8852 #_reflns_number_all 2672 _refine_ls_R_factor_all 0.0542 _refine_ls_wR_factor_all 0.0574 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.5\s(I) _reflns_number_gt 2100 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_gt 0.0561 _refine_ls_shift/su_max 0.003586 # 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: 1.48 1.45 0.459 ; #_publ_section_title # Title of paper - generally just the systematic or trivial name #; ? #; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. #loop_ # _publ_author_name # _publ_author_address # _publ_author_footnote # 'Other, Anthony N.' # Author 1 #; # ? # Address for author 1 #; #; # ? # Footnote for author 1 #; # 'Else, S. O.' # Author 2 #; # ? # Address 2 #; #; # ? # Footnote 2 #; #_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 0.3540(3) 0.8051(2) 0.6615(2) 0.0423 1.0000 Uani . . . . . . C2 C 0.3730(4) 0.8507(2) 0.7893(2) 0.0514 1.0000 Uani . . . . . . C3 C 0.5508(4) 0.8891(2) 0.8796(2) 0.0534 1.0000 Uani . . . . . . C4 C 0.7115(3) 0.8871(2) 0.84933(17) 0.0437 1.0000 Uani . . . . . . C5 C 0.6920(3) 0.84366(16) 0.72038(15) 0.0321 1.0000 Uani . . . . . . C6 C 0.5132(3) 0.80245(16) 0.62765(15) 0.0314 1.0000 Uani . . . . . . C11 C 0.8711(3) 0.4897(2) -0.2886(2) 0.0589 1.0000 Uani . . . . . . C12 C 0.8369(4) 0.5361(2) -0.1799(2) 0.0673 1.0000 Uani . . . . . . C13 C 0.7474(4) 0.4318(2) -0.11204(19) 0.0629 1.0000 Uani . . . . . . C14 C 0.7028(3) 0.2820(2) -0.15942(19) 0.0534 1.0000 Uani . . . . . . C15 C 0.7389(3) 0.2448(2) -0.2699(2) 0.0488 1.0000 Uani . . . . . . C16 C 0.7433(5) 0.4759(3) 0.0013(3) 0.0419 0.5841 Uani . . . . . . C17 C 0.7825(5) 0.6152(3) 0.0571(3) 0.0357 0.5841 Uani . . . . . . C18 C 0.7389(3) 0.65930(19) 0.18656(16) 0.0464 1.0000 Uani . . . . . . C19 C 0.8085(3) 0.81026(19) 0.23620(16) 0.0393 1.0000 Uani . . . . . . C20 C 0.8201(3) 0.8562(2) 0.35904(18) 0.0427 1.0000 Uani . . . . . . C21 C 0.6998(3) 0.6133(2) 0.3874(2) 0.0519 1.0000 Uani . . . . . . C22 C 0.6816(3) 0.5591(2) 0.26549(18) 0.0420 1.0000 Uani . . . . . . C26 C 0.6062(7) 0.4473(5) 0.0008(4) 0.0324 0.4159 Uani . . . . . . C27 C 0.6257(6) 0.6051(4) 0.0538(3) 0.0301 0.4159 Uani . . . . . . N11 N 0.8210(2) 0.34544(18) -0.33639(17) 0.0505 1.0000 Uani . . . . . . N12 N 0.7675(3) 0.76087(19) 0.43584(16) 0.0516 1.0000 Uani . . . . . . H21 H 0.2659 0.8550 0.8134 0.0531 1.0000 Uiso R . . . . . H31 H 0.5622 0.9198 0.9661 0.0571 1.0000 Uiso R . . . . . H41 H 0.8323 0.9134 0.9134 0.0515 1.0000 Uiso R . . . . . H61 H 0.4999 0.7732 0.5406 0.0355 1.0000 Uiso R . . . . . H111 H 0.9304 0.5627 -0.3336 0.0711 1.0000 Uiso R . . . . . H121 H 0.8827 0.6403 -0.1487 0.0802 1.0000 Uiso R . . . . . H141 H 0.6479 0.2066 -0.1149 0.0526 1.0000 Uiso R . . . . . H151 H 0.7065 0.1425 -0.3008 0.0604 1.0000 Uiso R . . . . . H161 H 0.7131 0.4012 0.0516 0.0306 0.5841 Uiso R . . . . . H171 H 0.8424 0.6938 0.0169 0.0306 0.5841 Uiso R . . . . . H191 H 0.8447 0.8815 0.1839 0.0476 1.0000 Uiso R . . . . . H201 H 0.8662 0.9600 0.3918 0.0437 1.0000 Uiso R . . . . . H211 H 0.6609 0.5445 0.4411 0.0592 1.0000 Uiso R . . . . . H221 H 0.6293 0.4545 0.2344 0.0509 1.0000 Uiso R . . . . . H261 H 0.6429 0.4043 0.0720 0.0306 0.4159 Uiso R . . . . . H271 H 0.6870 0.6718 0.0050 0.0306 0.4159 Uiso R . . . . . O1 O 0.1753(2) 0.76398(17) 0.57356(16) 0.0572 1.0000 Uani . . . . . . O2 O 0.85341(17) 0.84151(14) 0.69283(11) 0.0380 1.0000 Uani . . . . . . H1 H 0.1755 0.7259 0.4918 0.0600 1.0000 Uiso R . . . . . H2 H 0.8245 0.8133 0.6033 0.0450 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 0.0442(10) 0.0308(9) 0.0612(12) 0.0166(8) 0.0279(9) 0.0160(8) C2 0.0740(15) 0.0369(10) 0.0706(14) 0.0231(10) 0.0543(13) 0.0285(10) C3 0.0942(18) 0.0326(10) 0.0527(12) 0.0150(9) 0.0421(13) 0.0321(11) C4 0.0623(13) 0.0348(9) 0.0292(9) 0.0043(7) 0.0102(8) 0.0171(9) C5 0.0435(9) 0.0158(6) 0.0280(8) 0.0023(6) 0.0083(7) 0.0041(6) C6 0.0457(10) 0.0225(7) 0.0240(7) 0.0032(6) 0.0156(7) 0.0081(6) C11 0.0527(12) 0.0426(11) 0.0463(12) 0.0052(9) -0.0048(9) -0.0056(9) C12 0.0831(17) 0.0333(10) 0.0508(13) 0.0038(9) -0.0118(12) 0.0076(11) C13 0.0883(18) 0.0382(10) 0.0285(10) 0.0048(8) -0.0075(10) 0.0055(11) C14 0.0691(14) 0.0270(9) 0.0407(11) 0.0072(8) -0.0106(10) 0.0118(9) C15 0.0406(10) 0.0275(9) 0.0600(13) 0.0075(8) 0.0001(9) 0.0039(7) C16 0.058(2) 0.0341(16) 0.0442(18) 0.0203(14) 0.0274(16) 0.0196(15) C17 0.0445(17) 0.0280(13) 0.0272(14) 0.0047(11) 0.0078(12) 0.0087(12) C18 0.0565(12) 0.0278(8) 0.0302(9) 0.0057(7) -0.0087(8) 0.0046(8) C19 0.0445(10) 0.0301(8) 0.0357(9) 0.0093(7) 0.0079(8) 0.0090(7) C20 0.0421(10) 0.0356(9) 0.0488(11) 0.0055(8) 0.0185(8) 0.0113(8) C21 0.0592(13) 0.0465(11) 0.0668(13) 0.0247(10) 0.0430(11) 0.0211(10) C22 0.0392(10) 0.0320(9) 0.0459(11) 0.0127(8) 0.0030(8) 0.0101(7) C26 0.044(2) 0.035(2) 0.0234(18) 0.0084(15) 0.0131(17) 0.0192(18) C27 0.035(2) 0.0294(19) 0.0206(17) 0.0130(15) 0.0035(15) 0.0091(16) N11 0.0360(8) 0.0391(9) 0.0588(10) 0.0187(8) 0.0002(8) 0.0036(7) N12 0.0726(12) 0.0451(9) 0.0555(10) 0.0154(8) 0.0453(9) 0.0255(8) O1 0.0405(8) 0.0564(9) 0.0795(10) 0.0212(8) 0.0252(8) 0.0186(7) O2 0.0339(6) 0.0401(7) 0.0373(7) 0.0093(5) 0.0116(5) 0.0110(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.194(5) 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 . 1.400(3) yes C1 . C6 . 1.389(2) yes C1 . O1 . 1.368(2) yes C2 . C3 . 1.378(3) yes C2 . H21 . 0.950 no C3 . C4 . 1.379(3) yes C3 . H31 . 0.950 no C4 . C5 . 1.408(2) yes C4 . H41 . 0.950 no C5 . C6 . 1.392(2) yes C5 . O2 . 1.370(2) yes C6 . H61 . 0.950 no C11 . C12 . 1.373(3) yes C11 . N11 . 1.343(3) yes C11 . H111 . 0.950 no C12 . C13 . 1.399(3) yes C12 . H121 . 0.950 no C13 . C14 . 1.400(3) yes C13 . C16 . 1.305(4) yes C14 . C15 . 1.372(3) yes C14 . H141 . 0.950 no C15 . N11 . 1.345(3) yes C15 . H151 . 0.950 no C16 . C17 . 1.343(4) yes C16 . C26 . 0.996(5) yes C16 . H161 . 0.950 no C16 . H261 . 1.307 no C17 . C18 . 1.614(4) yes C17 . C26 . 1.650(5) yes C17 . C27 . 1.176(5) yes C17 . H171 . 0.950 no C17 . H271 . 1.149 no C18 . C19 . 1.384(2) yes C18 . C22 . 1.390(2) yes C18 . C27 . 1.443(4) yes C19 . C20 . 1.366(2) yes C19 . H191 . 0.950 no C20 . N12 . 1.334(2) yes C20 . H201 . 0.950 no C21 . C22 . 1.361(3) yes C21 . N12 . 1.353(3) yes C21 . H211 . 0.950 no C22 . H221 . 0.950 no C26 . C27 2_665 1.609(6) yes C26 . C27 . 1.548(5) yes C26 . H161 . 1.133 no C26 . H261 . 0.950 no C27 . H271 . 0.950 no H161 . H261 . 0.651 no O1 . H1 . 0.950 no O2 . H2 . 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 C2 . C1 . C6 . 120.1(2) yes C2 . C1 . O1 . 117.69(18) yes C6 . C1 . O1 . 122.19(18) yes C1 . C2 . C3 . 118.51(18) yes C1 . C2 . H21 . 120.9 no C3 . C2 . H21 . 120.6 no C2 . C3 . C4 . 122.84(18) yes C2 . C3 . H31 . 117.9 no C4 . C3 . H31 . 119.3 no C3 . C4 . C5 . 118.3(2) yes C3 . C4 . H41 . 121.3 no C5 . C4 . H41 . 120.5 no C4 . C5 . C6 . 119.89(17) yes C4 . C5 . O2 . 117.17(16) yes C6 . C5 . O2 . 122.94(14) yes C5 . C6 . C1 . 120.36(16) yes C5 . C6 . H61 . 120.0 no C1 . C6 . H61 . 119.7 no C12 . C11 . N11 . 123.3(2) yes C12 . C11 . H111 . 118.7 no N11 . C11 . H111 . 118.0 no C11 . C12 . C13 . 120.4(2) yes C11 . C12 . H121 . 118.9 no C13 . C12 . H121 . 120.6 no C12 . C13 . C14 . 116.1(2) yes C12 . C13 . C16 . 120.3(2) yes C14 . C13 . C16 . 122.2(2) yes C13 . C14 . C15 . 119.86(19) yes C13 . C14 . H141 . 119.9 no C15 . C14 . H141 . 120.2 no C14 . C15 . N11 . 123.73(18) yes C14 . C15 . H151 . 118.5 no N11 . C15 . H151 . 117.7 no C13 . C16 . C17 . 127.8(3) yes C13 . C16 . C26 . 109.8(4) yes C17 . C16 . C26 . 88.4(3) yes C13 . C16 . H161 . 116.2 no C17 . C16 . H161 . 115.9 no C26 . C16 . H161 . 71.2 no C13 . C16 . H261 . 130.8 no C17 . C16 . H261 . 97.6 no C26 . C16 . H261 . 46.3 no H161 . C16 . H261 . 28.3 no C16 . C17 . C18 . 125.5(2) yes C16 . C17 . C26 . 37.11(19) yes C18 . C17 . C26 . 100.2(2) yes C16 . C17 . C27 . 100.8(3) yes C18 . C17 . C27 . 59.9(2) yes C26 . C17 . C27 . 63.9(3) yes C16 . C17 . H171 . 116.5 no C18 . C17 . H171 . 118.0 no C26 . C17 . H171 . 132.6 no C27 . C17 . H171 . 111.1 no C16 . C17 . H271 . 116.2 no C18 . C17 . H271 . 89.0 no C26 . C17 . H271 . 92.2 no C27 . C17 . H271 . 48.2 no H171 . C17 . H271 . 63.4 no C17 . C18 . C19 . 116.73(17) yes C17 . C18 . C22 . 123.58(18) yes C19 . C18 . C22 . 117.69(17) yes C17 . C18 . C27 . 44.8(2) yes C19 . C18 . C27 . 118.9(2) yes C22 . C18 . C27 . 114.0(2) yes C18 . C19 . C20 . 120.01(16) yes C18 . C19 . H191 . 119.8 no C20 . C19 . H191 . 120.2 no C19 . C20 . N12 . 122.66(17) yes C19 . C20 . H201 . 119.3 no N12 . C20 . H201 . 118.0 no C22 . C21 . N12 . 123.30(17) yes C22 . C21 . H211 . 118.7 no N12 . C21 . H211 . 118.0 no C18 . C22 . C21 . 118.99(17) yes C18 . C22 . H221 . 120.4 no C21 . C22 . H221 . 120.6 no C27 2_665 C26 . C17 . 131.0(3) yes C27 2_665 C26 . C16 . 159.4(4) yes C17 . C26 . C16 . 54.5(3) yes C27 2_665 C26 . C27 . 89.6(3) yes C17 . C26 . C27 . 43.0(2) yes C16 . C26 . C27 . 97.2(4) yes C27 2_665 C26 . H161 . 138.1 no C17 . C26 . H161 . 87.2 no C16 . C26 . H161 . 52.5 no C27 . C26 . H161 . 120.2 no C27 2_665 C26 . H261 . 112.2 no C17 . C26 . H261 . 96.4 no C16 . C26 . H261 . 84.3 no C27 . C26 . H261 . 107.2 no H161 . C26 . H261 . 35.0 no C26 . C27 . C26 2_665 90.4(3) yes C26 . C27 . C18 . 113.7(3) yes C26 2_665 C27 . C18 . 124.9(3) yes C26 . C27 . C17 . 73.1(3) yes C26 2_665 C27 . C17 . 158.5(4) yes C18 . C27 . C17 . 75.3(3) yes C26 . C27 . H271 . 107.6 no C26 2_665 C27 . H271 . 109.6 no C18 . C27 . H271 . 108.6 no C17 . C27 . H271 . 64.4 no C15 . N11 . C11 . 116.6(2) yes C21 . N12 . C20 . 117.34(16) yes C26 . H161 . C16 . 56.3 no C26 . H161 . H261 . 56.9 no C16 . H161 . H261 . 108.0 no H161 . H261 . C26 . 88.0 no H161 . H261 . C16 . 43.8 no C26 . H261 . C16 . 49.3 no C17 . H271 . C27 . 67.4 no C1 . O1 . H1 . 110.7 no C5 . O2 . H2 . 109.9 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O1 . H1 . N11 2_665 179 0.95 1.81 2.764(2) yes O2 . H2 . N12 . 179 0.95 1.77 2.725(2) yes