# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 881423' #TrackingRef 'web_deposit_cif_file_0_MikelisV.veidis_1336635851.acridine_pyrogallol.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 9.450(2) _cell_length_b 11.830(2) _cell_length_c 11.964(2) _cell_angle_alpha 114.83(3) _cell_angle_beta 101.03(3) _cell_angle_gamma 94.64(3) _cell_volume 1171.8(5) _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' 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' _cell_formula_units_Z 2 # Given Formula = C30 H30 N2 O4 # Dc = 1.37 Fooo = 508.00 Mu = 0.91 M = 482.58 # Found Formula = C32 H24 N2 O3 # Dc = 1.37 FOOO = 508.00 Mu = 0.89 M = 484.55 _chemical_formula_sum 'C32 H24 N2 O3' _chemical_formula_moiety 'C32 H24 N2 O3' _chemical_compound_source ? _chemical_formula_weight 484.55 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_max 0.300 _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 0.089 # Sheldrick geometric approximatio 0.97 0.97 _exptl_absorpt_correction_type none # 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_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _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, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION' _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 22214 _reflns_number_total 5374 _diffrn_reflns_av_R_equivalents 0.024 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 5374 # Theoretical number of reflections is about 11051 _diffrn_reflns_theta_min 2.036 _diffrn_reflns_theta_max 27.822 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.039 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 0 _reflns_limit_h_min -12 _reflns_limit_h_max 11 _reflns_limit_k_min -15 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.20 _refine_diff_density_max 0.24 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 3646 _refine_ls_number_restraints 0 _refine_ls_number_parameters 334 _oxford_refine_ls_R_factor_ref 0.0387 _refine_ls_wR_factor_ref 0.0704 _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_shift/su_max 0.0004055 _refine_ls_shift/su_mean 0.0000318 # The values computed with all filters except I/sigma _oxford_reflns_number_all 5372 _refine_ls_R_factor_all 0.0626 _refine_ls_wR_factor_all 0.0741 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3962 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_gt 0.0710 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed # WARNING. The IUCr will not accept Unit Weights _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Quasi-Unit weights W = 1.0 or 1./2F ; # Insert your own references if required - in alphabetical order 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 0.51396(14) 0.93363(11) 0.34864(11) 0.0302 1.0000 Uani . . . . . . C2 C 0.43914(18) 0.97961(15) 0.27081(16) 0.0235 1.0000 Uani . . . . . . C3 C 0.36138(18) 1.07662(15) 0.32665(15) 0.0240 1.0000 Uani . . . . . . O4 O 0.35777(15) 1.12266(12) 0.45200(11) 0.0339 1.0000 Uani . . . . . . C5 C 0.28613(18) 1.13112(15) 0.25469(16) 0.0266 1.0000 Uani . . . . . . O6 O 0.20940(15) 1.22664(12) 0.30385(12) 0.0387 1.0000 Uani . . . . . . C7 C 0.28728(19) 1.08726(16) 0.12783(16) 0.0288 1.0000 Uani . . . . . . C8 C 0.36262(19) 0.98972(17) 0.07283(16) 0.0296 1.0000 Uani . . . . . . C9 C 0.43989(19) 0.93585(16) 0.14370(16) 0.0270 1.0000 Uani . . . . . . N10 N 0.66565(15) 0.75159(13) 0.22576(13) 0.0247 1.0000 Uani . . . . . . C11 C 0.77522(18) 0.77863(15) 0.17810(15) 0.0242 1.0000 Uani . . . . . . C12 C 0.8315(2) 0.90744(16) 0.21563(17) 0.0304 1.0000 Uani . . . . . . C13 C 0.9433(2) 0.93781(18) 0.17180(19) 0.0356 1.0000 Uani . . . . . . C14 C 1.0056(2) 0.84258(19) 0.0863(2) 0.0383 1.0000 Uani . . . . . . C15 C 0.9543(2) 0.71892(19) 0.04687(18) 0.0341 1.0000 Uani . . . . . . C16 C 0.83847(19) 0.68214(16) 0.09198(16) 0.0259 1.0000 Uani . . . . . . C17 C 0.78452(19) 0.55689(16) 0.05801(17) 0.0277 1.0000 Uani . . . . . . C18 C 0.67492(18) 0.52697(15) 0.10821(16) 0.0252 1.0000 Uani . . . . . . C19 C 0.61697(18) 0.62899(16) 0.19363(16) 0.0242 1.0000 Uani . . . . . . C20 C 0.5055(2) 0.59961(18) 0.24686(17) 0.0311 1.0000 Uani . . . . . . C21 C 0.4558(2) 0.47689(18) 0.21648(18) 0.0347 1.0000 Uani . . . . . . C22 C 0.5124(2) 0.37603(18) 0.13198(18) 0.0350 1.0000 Uani . . . . . . C23 C 0.6183(2) 0.40021(16) 0.07949(17) 0.0319 1.0000 Uani . . . . . . N24 N 0.83923(16) 0.63589(13) 0.46271(14) 0.0252 1.0000 Uani . . . . . . C25 C 0.79914(18) 0.51018(15) 0.42066(15) 0.0235 1.0000 Uani . . . . . . C26 C 0.86906(19) 0.41803(16) 0.33763(16) 0.0257 1.0000 Uani . . . . . . C27 C 0.98318(19) 0.46066(17) 0.29970(17) 0.0295 1.0000 Uani . . . . . . C28 C 1.02397(18) 0.58992(17) 0.33957(16) 0.0265 1.0000 Uani . . . . . . C29 C 0.94850(18) 0.67511(16) 0.42280(16) 0.0247 1.0000 Uani . . . . . . C30 C 0.9916(2) 0.80788(17) 0.46779(19) 0.0338 1.0000 Uani . . . . . . C31 C 1.1018(2) 0.85163(19) 0.4310(2) 0.0409 1.0000 Uani . . . . . . C32 C 1.1749(2) 0.7675(2) 0.3471(2) 0.0421 1.0000 Uani . . . . . . C33 C 1.1381(2) 0.6410(2) 0.30281(19) 0.0373 1.0000 Uani . . . . . . C34 C 0.8180(2) 0.28723(17) 0.29769(19) 0.0364 1.0000 Uani . . . . . . C35 C 0.7057(2) 0.25147(18) 0.3373(2) 0.0400 1.0000 Uani . . . . . . C36 C 0.6384(2) 0.34255(18) 0.42096(19) 0.0368 1.0000 Uani . . . . . . C37 C 0.68308(19) 0.46801(18) 0.46208(17) 0.0306 1.0000 Uani . . . . . . H71 H 0.2363 1.1230 0.0788 0.0316 1.0000 Uiso R . . . . . H81 H 0.3633 0.9607 -0.0121 0.0335 1.0000 Uiso R . . . . . H91 H 0.4920 0.8738 0.1088 0.0292 1.0000 Uiso R . . . . . H121 H 0.7912 0.9693 0.2712 0.0340 1.0000 Uiso R . . . . . H131 H 0.9798 1.0240 0.1999 0.0407 1.0000 Uiso R . . . . . H141 H 1.0828 0.8653 0.0573 0.0426 1.0000 Uiso R . . . . . H151 H 0.9937 0.6554 -0.0100 0.0385 1.0000 Uiso R . . . . . H171 H 0.8228 0.4910 0.0017 0.0308 1.0000 Uiso R . . . . . H201 H 0.4681 0.6675 0.3034 0.0348 1.0000 Uiso R . . . . . H211 H 0.3810 0.4571 0.2530 0.0398 1.0000 Uiso R . . . . . H221 H 0.4773 0.2919 0.1132 0.0399 1.0000 Uiso R . . . . . H231 H 0.6557 0.3338 0.0238 0.0361 1.0000 Uiso R . . . . . H271 H 1.0329 0.4008 0.2465 0.0328 1.0000 Uiso R . . . . . H301 H 0.9432 0.8631 0.5213 0.0390 1.0000 Uiso R . . . . . H311 H 1.1279 0.9379 0.4608 0.0469 1.0000 Uiso R . . . . . H321 H 1.2504 0.7999 0.3219 0.0468 1.0000 Uiso R . . . . . H331 H 1.1862 0.5840 0.2473 0.0413 1.0000 Uiso R . . . . . H341 H 0.8640 0.2271 0.2442 0.0418 1.0000 Uiso R . . . . . H351 H 0.6730 0.1664 0.3101 0.0463 1.0000 Uiso R . . . . . H361 H 0.5610 0.3146 0.4490 0.0404 1.0000 Uiso R . . . . . H371 H 0.6392 0.5286 0.5182 0.0338 1.0000 Uiso R . . . . . H11 H 0.5607 0.8814 0.3156 0.0423 1.0000 Uiso R . . . . . H41 H 0.4075 1.0876 0.4861 0.0468 1.0000 Uiso R . . . . . H61 H 0.2132 1.2511 0.3773 0.0526 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 0.0394(7) 0.0284(6) 0.0270(6) 0.0124(5) 0.0142(5) 0.0143(5) C2 0.0226(8) 0.0201(8) 0.0271(9) 0.0104(7) 0.0071(7) -0.0003(6) C3 0.0261(9) 0.0217(8) 0.0213(8) 0.0068(6) 0.0077(7) -0.0012(7) O4 0.0454(8) 0.0358(7) 0.0235(6) 0.0126(5) 0.0126(6) 0.0177(6) C5 0.0259(9) 0.0225(9) 0.0294(9) 0.0097(7) 0.0078(7) 0.0018(7) O6 0.0493(9) 0.0379(8) 0.0317(7) 0.0141(6) 0.0136(6) 0.0216(7) C7 0.0284(9) 0.0316(10) 0.0277(9) 0.0153(8) 0.0058(7) 0.0026(7) C8 0.0303(9) 0.0344(10) 0.0217(8) 0.0104(7) 0.0084(7) -0.0006(8) C9 0.0275(9) 0.0231(8) 0.0274(9) 0.0068(7) 0.0115(7) 0.0027(7) N10 0.0262(8) 0.0227(7) 0.0225(7) 0.0081(6) 0.0049(6) 0.0043(6) C11 0.0239(9) 0.0240(8) 0.0229(8) 0.0103(7) 0.0023(7) 0.0038(7) C12 0.0325(10) 0.0237(9) 0.0308(9) 0.0098(7) 0.0051(8) 0.0040(7) C13 0.0320(10) 0.0313(10) 0.0444(11) 0.0218(9) 0.0028(9) -0.0010(8) C14 0.0285(10) 0.0475(12) 0.0498(12) 0.0313(10) 0.0118(9) 0.0053(9) C15 0.0297(10) 0.0408(11) 0.0385(11) 0.0204(9) 0.0146(8) 0.0121(8) C16 0.0235(9) 0.0285(9) 0.0269(9) 0.0135(7) 0.0048(7) 0.0076(7) C17 0.0277(9) 0.0249(9) 0.0283(9) 0.0087(7) 0.0065(7) 0.0111(7) C18 0.0238(9) 0.0229(8) 0.0253(9) 0.0102(7) -0.0007(7) 0.0039(7) C19 0.0235(9) 0.0245(8) 0.0224(8) 0.0106(7) 0.0012(7) 0.0035(7) C20 0.0306(10) 0.0337(10) 0.0278(9) 0.0131(8) 0.0073(8) 0.0036(8) C21 0.0299(10) 0.0405(11) 0.0349(10) 0.0218(9) 0.0026(8) -0.0027(8) C22 0.0326(10) 0.0281(10) 0.0403(11) 0.0192(9) -0.0052(8) -0.0043(8) C23 0.0328(10) 0.0218(9) 0.0336(10) 0.0095(8) -0.0012(8) 0.0040(7) N24 0.0242(7) 0.0224(7) 0.0290(8) 0.0122(6) 0.0056(6) 0.0032(6) C25 0.0216(8) 0.0241(8) 0.0246(8) 0.0131(7) 0.0011(7) 0.0020(7) C26 0.0240(9) 0.0224(8) 0.0274(9) 0.0112(7) -0.0005(7) 0.0023(7) C27 0.0273(9) 0.0299(9) 0.0283(9) 0.0096(8) 0.0069(7) 0.0081(7) C28 0.0211(9) 0.0323(10) 0.0269(9) 0.0162(8) 0.0023(7) 0.0017(7) C29 0.0224(9) 0.0244(8) 0.0277(9) 0.0150(7) 0.0004(7) 0.0014(7) C30 0.0334(10) 0.0245(9) 0.0442(11) 0.0186(8) 0.0043(9) 0.0031(8) C31 0.0351(11) 0.0334(10) 0.0572(13) 0.0305(10) -0.0018(10) -0.0044(9) C32 0.0288(10) 0.0535(13) 0.0540(13) 0.0380(11) 0.0044(9) -0.0059(9) C33 0.0283(10) 0.0499(12) 0.0383(11) 0.0234(10) 0.0103(8) 0.0043(9) C34 0.0346(11) 0.0209(9) 0.0451(11) 0.0106(8) 0.0006(9) 0.0044(8) C35 0.0348(11) 0.0238(9) 0.0559(13) 0.0216(9) -0.0056(9) -0.0060(8) C36 0.0284(10) 0.0392(11) 0.0457(12) 0.0275(10) 0.0003(9) -0.0061(8) C37 0.0265(9) 0.0347(10) 0.0322(10) 0.0175(8) 0.0063(8) 0.0014(8) _refine_ls_extinction_coef 0.001 _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.3446(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C2 . 1.378(2) yes O1 . H11 . 0.800 no C2 . C3 . 1.409(2) yes C2 . C9 . 1.387(2) yes C3 . O4 . 1.372(2) yes C3 . C5 . 1.403(2) yes O4 . H41 . 0.812 no C5 . O6 . 1.373(2) yes C5 . C7 . 1.385(2) yes O6 . H61 . 0.794 no C7 . C8 . 1.395(3) yes C7 . H71 . 0.942 no C8 . C9 . 1.397(3) yes C8 . H81 . 0.928 no C9 . H91 . 0.914 no N10 . C11 . 1.351(2) yes N10 . C19 . 1.349(2) yes C11 . C12 . 1.418(2) yes C11 . C16 . 1.442(2) yes C12 . C13 . 1.352(3) yes C12 . H121 . 0.926 no C13 . C14 . 1.425(3) yes C13 . H131 . 0.939 no C14 . C15 . 1.347(3) yes C14 . H141 . 0.931 no C15 . C16 . 1.423(2) yes C15 . H151 . 0.938 no C16 . C17 . 1.383(2) yes C17 . C18 . 1.384(2) yes C17 . H171 . 0.943 no C18 . C19 . 1.444(2) yes C18 . C23 . 1.421(2) yes C19 . C20 . 1.421(2) yes C20 . C21 . 1.357(3) yes C20 . H201 . 0.953 no C21 . C22 . 1.425(3) yes C21 . H211 . 0.960 no C22 . C23 . 1.350(3) yes C22 . H221 . 0.938 no C23 . H231 . 0.939 no N24 . C25 . 1.347(2) yes N24 . C29 . 1.344(2) yes C25 . C26 . 1.439(2) yes C25 . C37 . 1.423(2) yes C26 . C27 . 1.384(2) yes C26 . C34 . 1.423(2) yes C27 . C28 . 1.392(2) yes C27 . H271 . 0.957 no C28 . C29 . 1.436(2) yes C28 . C33 . 1.422(3) yes C29 . C30 . 1.423(2) yes C30 . C31 . 1.351(3) yes C30 . H301 . 0.925 no C31 . C32 . 1.419(3) yes C31 . H311 . 0.922 no C32 . C33 . 1.349(3) yes C32 . H321 . 0.939 no C33 . H331 . 0.944 no C34 . C35 . 1.348(3) yes C34 . H341 . 0.938 no C35 . C36 . 1.420(3) yes C35 . H351 . 0.922 no C36 . C37 . 1.353(3) yes C36 . H361 . 0.951 no C37 . H371 . 0.942 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 . O1 . H11 . 114.8 no O1 . C2 . C3 . 116.81(14) yes O1 . C2 . C9 . 122.97(15) yes C3 . C2 . C9 . 120.21(16) yes C2 . C3 . O4 . 122.10(15) yes C2 . C3 . C5 . 120.25(15) yes O4 . C3 . C5 . 117.64(15) yes C3 . O4 . H41 . 110.2 no C3 . C5 . O6 . 123.03(15) yes C3 . C5 . C7 . 119.35(16) yes O6 . C5 . C7 . 117.61(16) yes C5 . O6 . H61 . 115.0 no C5 . C7 . C8 . 119.97(17) yes C5 . C7 . H71 . 119.8 no C8 . C7 . H71 . 120.3 no C7 . C8 . C9 . 121.35(16) yes C7 . C8 . H81 . 119.7 no C9 . C8 . H81 . 118.9 no C8 . C9 . C2 . 118.85(16) yes C8 . C9 . H91 . 121.7 no C2 . C9 . H91 . 119.5 no C11 . N10 . C19 . 118.07(15) yes N10 . C11 . C12 . 118.53(16) yes N10 . C11 . C16 . 122.81(15) yes C12 . C11 . C16 . 118.65(16) yes C11 . C12 . C13 . 120.02(18) yes C11 . C12 . H121 . 118.6 no C13 . C12 . H121 . 121.4 no C12 . C13 . C14 . 121.40(18) yes C12 . C13 . H131 . 118.1 no C14 . C13 . H131 . 120.5 no C13 . C14 . C15 . 120.60(18) yes C13 . C14 . H141 . 120.2 no C15 . C14 . H141 . 119.2 no C14 . C15 . C16 . 120.12(18) yes C14 . C15 . H151 . 121.4 no C16 . C15 . H151 . 118.5 no C11 . C16 . C15 . 119.18(16) yes C11 . C16 . C17 . 118.12(16) yes C15 . C16 . C17 . 122.69(17) yes C16 . C17 . C18 . 120.12(16) yes C16 . C17 . H171 . 120.7 no C18 . C17 . H171 . 119.2 no C17 . C18 . C19 . 118.44(16) yes C17 . C18 . C23 . 122.55(17) yes C19 . C18 . C23 . 119.01(17) yes C18 . C19 . N10 . 122.40(16) yes C18 . C19 . C20 . 118.99(16) yes N10 . C19 . C20 . 118.61(16) yes C19 . C20 . C21 . 119.52(18) yes C19 . C20 . H201 . 118.5 no C21 . C20 . H201 . 122.0 no C20 . C21 . C22 . 121.62(18) yes C20 . C21 . H211 . 119.5 no C22 . C21 . H211 . 118.9 no C21 . C22 . C23 . 120.57(17) yes C21 . C22 . H221 . 120.2 no C23 . C22 . H221 . 119.3 no C18 . C23 . C22 . 120.29(18) yes C18 . C23 . H231 . 119.1 no C22 . C23 . H231 . 120.6 no C25 . N24 . C29 . 117.55(15) yes N24 . C25 . C26 . 123.07(16) yes N24 . C25 . C37 . 117.83(16) yes C26 . C25 . C37 . 119.10(16) yes C25 . C26 . C27 . 118.39(16) yes C25 . C26 . C34 . 118.82(17) yes C27 . C26 . C34 . 122.79(17) yes C26 . C27 . C28 . 119.45(17) yes C26 . C27 . H271 . 119.5 no C28 . C27 . H271 . 121.0 no C27 . C28 . C29 . 118.34(16) yes C27 . C28 . C33 . 122.87(18) yes C29 . C28 . C33 . 118.79(17) yes C28 . C29 . N24 . 123.17(15) yes C28 . C29 . C30 . 119.19(16) yes N24 . C29 . C30 . 117.63(17) yes C29 . C30 . C31 . 119.67(19) yes C29 . C30 . H301 . 119.4 no C31 . C30 . H301 . 120.9 no C30 . C31 . C32 . 121.24(19) yes C30 . C31 . H311 . 118.5 no C32 . C31 . H311 . 120.3 no C31 . C32 . C33 . 121.01(19) yes C31 . C32 . H321 . 119.9 no C33 . C32 . H321 . 119.1 no C28 . C33 . C32 . 120.1(2) yes C28 . C33 . H331 . 118.0 no C32 . C33 . H331 . 121.9 no C26 . C34 . C35 . 120.05(19) yes C26 . C34 . H341 . 118.9 no C35 . C34 . H341 . 121.1 no C34 . C35 . C36 . 121.09(18) yes C34 . C35 . H351 . 119.2 no C36 . C35 . H351 . 119.7 no C35 . C36 . C37 . 121.21(18) yes C35 . C36 . H361 . 119.2 no C37 . C36 . H361 . 119.5 no C25 . C37 . C36 . 119.71(18) yes C25 . C37 . H371 . 118.9 no C36 . C37 . H371 . 121.4 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 . H11 . N10 . 176.51(5) 0.800 1.940 2.739(3) yes O4 . H41 . O1 2_676 148.02(5) 0.812 2.099 2.821(3) yes O6 . H61 . N24 2_676 151.89(6) 0.794 2.004 2.730(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 05/04/12 at 14:44:56 # #LIST 12 BLOCK SCALE X'S, U'S RIDE O ( 1,X'S) H ( 11,X'S) RIDE O ( 4,X'S) H ( 41,X'S) RIDE O ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 32,X'S) H ( 321,X'S) RIDE C ( 33,X'S) H ( 331,X'S) RIDE C ( 34,X'S) H ( 341,X'S) RIDE C ( 35,X'S) H ( 351,X'S) RIDE C ( 36,X'S) H ( 361,X'S) RIDE C ( 37,X'S) H ( 371,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 05/04/12 at 14:44:56 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 0 -1 1 x . -1 0 1 x . data_1 _database_code_depnum_ccdc_archive 'CCDC 881427' #TrackingRef 'web_deposit_cif_file_0_MikelisV.veidis_1336637414.Bipyridine_pyrogallol trihydrate .cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 14.931(3) _cell_length_b 15.372(3) _cell_length_c 15.647(3) _cell_angle_alpha 60.72(3) _cell_angle_beta 67.16(3) _cell_angle_gamma 67.07(3) _cell_volume 2796.3(13) _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' 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' _cell_formula_units_Z 2 # Given Formula = C63 H60 N9 O12 # Dc = 1.35 Fooo = 1194.00 Mu = 0.95 M = 1135.22 # Found Formula = C63 H60 N9 O12 # Dc = 1.35 FOOO = 1194.00 Mu = 0.95 M = 1135.22 _chemical_formula_sum 'C63 H60 N9 O12' _chemical_formula_moiety 'C63 H60 N9 O12' _chemical_compound_source ? _chemical_formula_weight 1135.22 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1194 _exptl_absorpt_coefficient_mu 0.095 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9812 _exptl_absorpt_correction_T_max 0.9812 # 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_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 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 173 _diffrn_reflns_number 44628 _reflns_number_total 12742 _diffrn_reflns_av_R_equivalents 0.048 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 12742 # Theoretical number of reflections is about 25691 _diffrn_reflns_theta_min 2.421 _diffrn_reflns_theta_max 27.499 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.299 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -17 _reflns_limit_h_max 19 _reflns_limit_k_min -16 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _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 -0.29 _refine_diff_density_max 0.46 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 6876 _refine_ls_number_restraints 0 _refine_ls_number_parameters 757 _oxford_refine_ls_R_factor_ref 0.0483 _refine_ls_wR_factor_ref 0.1299 _refine_ls_goodness_of_fit_ref 1.0472 _refine_ls_shift/su_max 0.0001694 _refine_ls_shift/su_mean 0.0000170 # The values computed from all data _oxford_reflns_number_all 12740 _refine_ls_R_factor_all 0.0989 _refine_ls_wR_factor_all 0.2117 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7344 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_gt 0.1347 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 3.41P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens O1 O 0.28859(16) 0.05617(18) 0.1435(2) 0.0508 1.0000 Uani . . . . . . . O2 O -0.11403(14) 0.28246(16) 0.15924(17) 0.0341 1.0000 Uani . . . . . . . O3 O 0.21446(14) 0.59102(15) 0.49422(16) 0.0312 1.0000 Uani . . . . . . . O4 O 0.07411(14) 0.15545(15) 0.16837(17) 0.0303 1.0000 Uani . . . . . . . O5 O 0.26176(14) 0.20861(15) 0.18580(17) 0.0326 1.0000 Uani . . . . . . . O6 O 0.04924(15) 0.31320(16) 0.20124(17) 0.0338 1.0000 Uani . . . . . . . O7 O 0.39750(15) 0.45844(16) 0.51996(17) 0.0329 1.0000 Uani . . . . . . . O8 O 0.20584(15) 0.38581(15) 0.19642(17) 0.0353 1.0000 Uani . . . . . . . O9 O 0.12962(14) -0.01942(15) 0.15268(17) 0.0311 1.0000 Uani . . . . . . . C10 C 0.51132(19) 0.5547(2) 0.1701(2) 0.0218 1.0000 Uani . . . . . . . O11 O 0.45563(15) 0.28335(16) 0.50316(18) 0.0369 1.0000 Uani . . . . . . . C12 C 0.08206(19) 0.2715(2) 0.8042(2) 0.0213 1.0000 Uani . . . . . . . C13 C 0.2393(2) 0.5035(2) 0.4797(2) 0.0236 1.0000 Uani . . . . . . . N14 N 0.02974(18) 0.7217(2) 0.4752(2) 0.0326 1.0000 Uani . . . . . . . C15 C 0.41339(19) 0.63304(19) 0.1710(2) 0.0215 1.0000 Uani . . . . . . . O16 O 0.45696(14) 0.09433(15) 0.17131(17) 0.0317 1.0000 Uani . . . . . . . N17 N 0.44837(19) 0.8831(2) 0.1592(2) 0.0380 1.0000 Uani . . . . . . . N18 N 0.35102(17) 0.02613(19) 0.8288(2) 0.0326 1.0000 Uani . . . . . . . C19 C 0.3031(2) 0.3175(2) 0.4565(2) 0.0296 1.0000 Uani . . . . . . . C20 C 0.0340(2) 0.0365(2) 0.1443(2) 0.0226 1.0000 Uani . . . . . . . C21 C 0.3630(2) 0.6628(2) 0.2519(2) 0.0260 1.0000 Uani . . . . . . . C22 C -0.1584(2) 0.1634(2) 0.1311(2) 0.0267 1.0000 Uani . . . . . . . C23 C 0.3637(2) 0.3435(2) 0.4845(2) 0.0263 1.0000 Uani . . . . . . . C24 C -0.0923(2) 0.1929(2) 0.1487(2) 0.0227 1.0000 Uani . . . . . . . C25 C 0.5376(2) 0.4780(2) 0.2588(2) 0.0253 1.0000 Uani . . . . . . . C26 C 0.3053(2) 0.3373(2) 0.1909(2) 0.0225 1.0000 Uani . . . . . . . C27 C 0.4346(2) 0.1866(2) 0.1768(2) 0.0224 1.0000 Uani . . . . . . . C28 C 0.7444(2) 0.5643(2) 0.2426(2) 0.0294 1.0000 Uani . . . . . . . O29 O 0.60792(18) 0.35924(19) 0.5117(3) 0.0661 1.0000 Uani . . . . . . . C30 C 0.6289(2) 0.4060(2) 0.2534(2) 0.0304 1.0000 Uani . . . . . . . C31 C -0.0114(2) 0.4369(2) 0.7107(2) 0.0338 1.0000 Uani . . . . . . . N32 N 0.9095(2) 0.5006(2) 0.1528(2) 0.0370 1.0000 Uani . . . . . . . C33 C 0.4741(2) 0.3192(2) 0.1851(3) 0.0343 1.0000 Uani . . . . . . . C34 C -0.0915(2) 0.8610(2) 0.3889(2) 0.0328 1.0000 Uani . . . . . . . C35 C 0.3745(2) 0.3754(2) 0.1921(2) 0.0310 1.0000 Uani . . . . . . . C36 C 0.2730(2) 0.7385(2) 0.2468(2) 0.0318 1.0000 Uani . . . . . . . C37 C 0.1796(2) 0.4775(2) 0.4506(2) 0.0298 1.0000 Uani . . . . . . . N38 N 0.7639(2) 0.1838(2) 0.5124(2) 0.0419 1.0000 Uani . . . . . . . C39 C 0.5046(2) 0.2250(2) 0.1775(2) 0.0297 1.0000 Uani . . . . . . . C40 C 0.8017(2) 0.6591(2) 0.0659(2) 0.0321 1.0000 Uani . . . . . . . N41 N -0.4343(2) 1.1018(2) 0.4839(2) 0.0427 1.0000 Uani . . . . . . . C42 C 0.0764(2) 0.3589(2) 0.7148(2) 0.0283 1.0000 Uani . . . . . . . C43 C -0.0018(2) 0.2661(2) 0.8849(2) 0.0284 1.0000 Uani . . . . . . . C44 C 0.8363(2) 0.4925(2) 0.2375(3) 0.0353 1.0000 Uani . . . . . . . C45 C 0.3246(2) 0.0842(2) 0.7412(3) 0.0356 1.0000 Uani . . . . . . . C46 C 0.2387(2) 0.1652(2) 0.7287(2) 0.0280 1.0000 Uani . . . . . . . C47 C 0.6708(2) 0.4811(2) 0.0814(3) 0.0340 1.0000 Uani . . . . . . . C48 C 0.7257(2) 0.6501(2) 0.1548(2) 0.0240 1.0000 Uani . . . . . . . C49 C 0.5807(2) 0.5555(2) 0.0792(2) 0.0298 1.0000 Uani . . . . . . . C50 C 0.5909(2) 0.7902(2) 0.0710(2) 0.0312 1.0000 Uani . . . . . . . C51 C 0.2027(2) 0.1261(2) 0.9044(2) 0.0251 1.0000 Uani . . . . . . . N52 N 0.23076(18) 0.78494(19) 0.1693(2) 0.0326 1.0000 Uani . . . . . . . C53 C 0.2789(2) 0.7548(2) 0.0926(3) 0.0381 1.0000 Uani . . . . . . . C54 C 0.3684(2) 0.6797(2) 0.0909(2) 0.0324 1.0000 Uani . . . . . . . C55 C 0.5731(2) 0.7477(2) 0.2440(2) 0.0311 1.0000 Uani . . . . . . . N56 N -0.09222(19) 0.43308(18) 0.7886(2) 0.0330 1.0000 Uani . . . . . . . C57 C -0.2504(2) 0.9522(2) 0.4797(2) 0.0245 1.0000 Uani . . . . . . . C58 C 0.6285(2) 0.7297(2) 0.1566(2) 0.0241 1.0000 Uani . . . . . . . C59 C -0.15257(19) 0.8729(2) 0.4779(2) 0.0230 1.0000 Uani . . . . . . . C60 C -0.0862(2) 0.3484(2) 0.8735(3) 0.0342 1.0000 Uani . . . . . . . C61 C 0.9505(2) 0.0381(2) 0.5027(2) 0.0255 1.0000 Uani . . . . . . . C62 C 0.17562(19) 0.18621(19) 0.8129(2) 0.0204 1.0000 Uani . . . . . . . N63 N 0.69563(17) 0.40546(19) 0.1663(2) 0.0315 1.0000 Uani . . . . . . . C64 C 0.00443(19) 0.1303(2) 0.1546(2) 0.0214 1.0000 Uani . . . . . . . C65 C 0.9234(2) 0.1204(3) 0.4171(3) 0.0390 1.0000 Uani . . . . . . . C66 C -0.0025(2) 0.7857(3) 0.3910(3) 0.0369 1.0000 Uani . . . . . . . C67 C 0.3332(2) 0.4367(2) 0.4949(2) 0.0230 1.0000 Uani . . . . . . . C68 C 0.2905(2) 0.0481(2) 0.9085(2) 0.0293 1.0000 Uani . . . . . . . C69 C -0.0282(2) 0.7336(2) 0.5606(2) 0.0293 1.0000 Uani . . . . . . . C70 C 0.4848(2) 0.8242(2) 0.2412(3) 0.0391 1.0000 Uani . . . . . . . C71 C -0.1193(2) 0.8067(2) 0.5660(2) 0.0264 1.0000 Uani . . . . . . . C72 C 0.33438(19) 0.2429(2) 0.1831(2) 0.0213 1.0000 Uani . . . . . . . C73 C 0.8313(3) 0.1896(3) 0.4257(3) 0.0445 1.0000 Uani . . . . . . . C74 C -0.1271(2) 0.0711(2) 0.1190(2) 0.0273 1.0000 Uani . . . . . . . C75 C 0.2118(2) 0.3856(2) 0.4387(2) 0.0330 1.0000 Uani . . . . . . . C76 C -0.2722(3) 1.0345(3) 0.3924(3) 0.0473 1.0000 Uani . . . . . . . C77 C 0.8804(3) 0.0313(3) 0.5938(3) 0.0463 1.0000 Uani . . . . . . . C78 C -0.3644(3) 1.1064(3) 0.3983(3) 0.0543 1.0000 Uani . . . . . . . C79 C -0.0309(2) 0.0080(2) 0.1251(2) 0.0263 1.0000 Uani . . . . . . . C80 C 0.5018(2) 0.8650(2) 0.0760(3) 0.0363 1.0000 Uani . . . . . . . C81 C 0.8916(2) 0.5833(3) 0.0695(3) 0.0373 1.0000 Uani . . . . . . . C82 C -0.3218(3) 0.9484(3) 0.5670(3) 0.0700 1.0000 Uani . . . . . . . C83 C 0.7893(3) 0.1049(3) 0.5945(3) 0.0538 1.0000 Uani . . . . . . . C84 C -0.4111(3) 1.0248(3) 0.5651(3) 0.0757 1.0000 Uani . . . . . . . H191 H 0.3236 0.2528 0.4518 0.0355 1.0000 Uiso R . . . . . . H211 H 0.3890 0.6341 0.3087 0.0304 1.0000 Uiso R . . . . . . H221 H -0.2225 0.2074 0.1237 0.0319 1.0000 Uiso R . . . . . . H251 H 0.4951 0.4727 0.3225 0.0315 1.0000 Uiso R . . . . . . H281 H 0.6941 0.5549 0.3051 0.0356 1.0000 Uiso R . . . . . . H301 H 0.6434 0.3528 0.3146 0.0368 1.0000 Uiso R . . . . . . H311 H -0.0136 0.4969 0.6499 0.0412 1.0000 Uiso R . . . . . . H331 H 0.5199 0.3452 0.1869 0.0403 1.0000 Uiso R . . . . . . H341 H -0.1134 0.9045 0.3274 0.0405 1.0000 Uiso R . . . . . . H351 H 0.3557 0.4393 0.1959 0.0370 1.0000 Uiso R . . . . . . H361 H 0.2390 0.7593 0.3005 0.0398 1.0000 Uiso R . . . . . . H371 H 0.1174 0.5225 0.4409 0.0351 1.0000 Uiso R . . . . . . H391 H 0.5740 0.1862 0.1739 0.0356 1.0000 Uiso R . . . . . . H401 H 0.7945 0.7161 0.0047 0.0380 1.0000 Uiso R . . . . . . H421 H 0.1307 0.3653 0.6585 0.0351 1.0000 Uiso R . . . . . . H431 H -0.0026 0.2077 0.9477 0.0351 1.0000 Uiso R . . . . . . H441 H 0.8475 0.4346 0.2971 0.0424 1.0000 Uiso R . . . . . . H451 H 0.3675 0.0677 0.6855 0.0426 1.0000 Uiso R . . . . . . H461 H 0.2246 0.2050 0.6640 0.0329 1.0000 Uiso R . . . . . . H471 H 0.7193 0.4804 0.0207 0.0402 1.0000 Uiso R . . . . . . H491 H 0.5666 0.6056 0.0164 0.0343 1.0000 Uiso R . . . . . . H501 H 0.6240 0.7821 0.0091 0.0383 1.0000 Uiso R . . . . . . H511 H 0.1623 0.1388 0.9632 0.0295 1.0000 Uiso R . . . . . . H531 H 0.2503 0.7851 0.0374 0.0450 1.0000 Uiso R . . . . . . H541 H 0.4000 0.6606 0.0336 0.0383 1.0000 Uiso R . . . . . . H551 H 0.5969 0.7080 0.3042 0.0366 1.0000 Uiso R . . . . . . H601 H -0.1425 0.3446 0.9291 0.0411 1.0000 Uiso R . . . . . . H651 H 0.9667 0.1292 0.3549 0.0481 1.0000 Uiso R . . . . . . H661 H 0.0369 0.7789 0.3295 0.0456 1.0000 Uiso R . . . . . . H681 H 0.3092 0.0085 0.9700 0.0347 1.0000 Uiso R . . . . . . H691 H -0.0068 0.6897 0.6201 0.0342 1.0000 Uiso R . . . . . . H701 H 0.4482 0.8360 0.3007 0.0456 1.0000 Uiso R . . . . . . H711 H -0.1546 0.8086 0.6294 0.0316 1.0000 Uiso R . . . . . . H731 H 0.8164 0.2430 0.3668 0.0534 1.0000 Uiso R . . . . . . H741 H -0.1725 0.0525 0.1062 0.0335 1.0000 Uiso R . . . . . . H751 H 0.1728 0.3687 0.4167 0.0399 1.0000 Uiso R . . . . . . H761 H -0.2262 1.0426 0.3301 0.0569 1.0000 Uiso R . . . . . . H771 H 0.8944 -0.0205 0.6540 0.0567 1.0000 Uiso R . . . . . . H781 H -0.3787 1.1622 0.3396 0.0664 1.0000 Uiso R . . . . . . H791 H -0.0098 -0.0560 0.1173 0.0314 1.0000 Uiso R . . . . . . H801 H 0.4776 0.9056 0.0173 0.0452 1.0000 Uiso R . . . . . . H811 H 0.9413 0.5886 0.0110 0.0439 1.0000 Uiso R . . . . . . H821 H -0.3135 0.8959 0.6279 0.0845 1.0000 Uiso R . . . . . . H831 H 0.7430 0.0989 0.6583 0.0639 1.0000 Uiso R . . . . . . H841 H -0.4599 1.0222 0.6259 0.0908 1.0000 Uiso R . . . . . . H51 H 0.2802 0.1588 0.1705 0.0491 1.0000 Uiso R . . . . . . H91 H 0.1367 -0.0756 0.1542 0.0472 1.0000 Uiso R . . . . . . H161 H 0.5165 0.0693 0.1672 0.0468 1.0000 Uiso R . . . . . . H81 H 0.1920 0.4400 0.2020 0.0525 1.0000 Uiso R . . . . . . H41 H 0.0573 0.2097 0.1751 0.0450 1.0000 Uiso R . . . . . . H21 H -0.1720 0.3126 0.1537 0.0505 1.0000 Uiso R . . . . . . H31 H 0.1572 0.6173 0.4876 0.0468 1.0000 Uiso R . . . . . . H71 H 0.3813 0.5209 0.5090 0.0491 1.0000 Uiso R . . . . . . H111 H 0.4689 0.2321 0.4933 0.0559 1.0000 Uiso R . . . . . . H12 H 0.3267 -0.0039 0.1659 0.0737 1.0000 Uiso R . . . . . . H292 H 0.5569 0.3539 0.5095 0.0960 1.0000 Uiso R . . . . . . H291 H 0.6548 0.3095 0.5129 0.0960 1.0000 Uiso R . . . . . . H62 H 0.1076 0.3171 0.1885 0.0520 1.0000 Uiso R . . . . . . H11 H 0.2327 0.0498 0.1515 0.0739 1.0000 Uiso R . . . . . . H61 H 0.0235 0.3590 0.1553 0.0539 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 0.0220(11) 0.0387(13) 0.109(2) -0.0466(15) -0.0222(13) 0.0048(10) O2 0.0169(9) 0.0315(11) 0.0601(15) -0.0292(11) -0.0172(10) 0.0102(8) O3 0.0195(10) 0.0293(10) 0.0471(13) -0.0209(10) -0.0148(9) 0.0059(8) O4 0.0178(9) 0.0243(10) 0.0558(14) -0.0234(10) -0.0163(9) 0.0050(8) O5 0.0174(9) 0.0284(10) 0.0605(15) -0.0288(11) -0.0135(9) 0.0045(8) O6 0.0227(10) 0.0320(11) 0.0532(14) -0.0217(10) -0.0181(10) 0.0018(9) O7 0.0230(10) 0.0260(10) 0.0533(14) -0.0185(10) -0.0200(10) 0.0045(8) O8 0.0243(11) 0.0251(10) 0.0591(15) -0.0252(11) -0.0144(10) 0.0066(9) O9 0.0240(10) 0.0207(10) 0.0501(13) -0.0182(9) -0.0161(9) 0.0054(8) C10 0.0176(13) 0.0183(12) 0.0289(15) -0.0099(11) -0.0061(11) -0.0028(10) O11 0.0277(11) 0.0251(11) 0.0576(15) -0.0207(11) -0.0195(11) 0.0083(9) C12 0.0180(13) 0.0187(12) 0.0267(15) -0.0097(11) -0.0090(11) 0.0002(11) C13 0.0201(13) 0.0233(13) 0.0210(14) -0.0071(11) -0.0047(11) -0.0016(11) N14 0.0205(12) 0.0328(14) 0.0469(16) -0.0214(13) -0.0112(11) 0.0011(11) C15 0.0176(12) 0.0154(12) 0.0271(15) -0.0073(11) -0.0053(11) -0.0018(10) O16 0.0172(9) 0.0251(10) 0.0563(14) -0.0241(10) -0.0140(9) 0.0067(8) N17 0.0257(13) 0.0265(13) 0.0618(19) -0.0205(13) -0.0155(13) 0.0021(11) N18 0.0161(11) 0.0287(13) 0.0515(17) -0.0205(12) -0.0114(11) 0.0050(10) C19 0.0332(16) 0.0240(14) 0.0312(16) -0.0104(12) -0.0111(13) -0.0042(13) C20 0.0213(13) 0.0198(13) 0.0202(14) -0.0059(11) -0.0057(11) -0.0009(11) C21 0.0250(14) 0.0245(14) 0.0256(15) -0.0102(12) -0.0065(11) -0.0028(12) C22 0.0183(13) 0.0307(15) 0.0272(15) -0.0099(12) -0.0080(11) -0.0024(12) C23 0.0206(14) 0.0227(14) 0.0263(15) -0.0064(12) -0.0070(11) 0.0002(12) C24 0.0173(13) 0.0225(13) 0.0248(14) -0.0104(11) -0.0067(11) 0.0011(11) C25 0.0196(13) 0.0242(13) 0.0280(15) -0.0106(12) -0.0062(11) -0.0008(11) C26 0.0206(13) 0.0203(13) 0.0243(14) -0.0106(11) -0.0073(11) 0.0011(11) C27 0.0202(13) 0.0208(13) 0.0227(14) -0.0080(11) -0.0070(11) -0.0007(11) C28 0.0294(15) 0.0246(14) 0.0352(17) -0.0135(13) -0.0137(13) 0.0001(12) O29 0.0289(13) 0.0384(13) 0.149(3) -0.0493(17) -0.0423(16) 0.0104(11) C30 0.0238(14) 0.0244(14) 0.0401(18) -0.0129(13) -0.0150(13) 0.0040(12) C31 0.0367(17) 0.0215(14) 0.0375(18) -0.0048(13) -0.0190(14) -0.0009(13) N32 0.0301(14) 0.0337(14) 0.0515(18) -0.0248(13) -0.0171(13) 0.0054(12) C33 0.0280(15) 0.0378(17) 0.048(2) -0.0218(15) -0.0111(14) -0.0106(14) C34 0.0232(14) 0.0391(17) 0.0283(16) -0.0132(14) -0.0052(12) -0.0017(13) C35 0.0341(16) 0.0240(14) 0.0382(18) -0.0171(13) -0.0081(14) -0.0047(13) C36 0.0258(15) 0.0245(14) 0.0376(18) -0.0158(13) -0.0050(13) 0.0025(12) C37 0.0214(14) 0.0322(15) 0.0328(16) -0.0129(13) -0.0115(12) 0.0009(12) N38 0.0281(14) 0.0347(15) 0.066(2) -0.0291(15) -0.0156(14) 0.0057(12) C39 0.0177(13) 0.0321(16) 0.0386(17) -0.0159(14) -0.0101(12) 0.0002(12) C40 0.0287(15) 0.0278(15) 0.0336(17) -0.0118(13) -0.0092(13) -0.0001(13) N41 0.0335(15) 0.0346(15) 0.061(2) -0.0233(14) -0.0252(15) 0.0099(12) C42 0.0271(14) 0.0237(14) 0.0283(16) -0.0054(12) -0.0093(12) -0.0047(12) C43 0.0229(14) 0.0256(14) 0.0273(15) -0.0089(12) -0.0051(12) -0.0003(12) C44 0.0347(17) 0.0270(15) 0.0458(19) -0.0153(14) -0.0222(15) 0.0041(13) C45 0.0184(14) 0.0408(17) 0.047(2) -0.0285(16) -0.0015(13) 0.0010(13) C46 0.0214(14) 0.0314(15) 0.0285(16) -0.0135(13) -0.0054(12) -0.0026(12) C47 0.0239(15) 0.0329(16) 0.0401(18) -0.0202(14) -0.0016(13) -0.0009(13) C48 0.0212(13) 0.0210(13) 0.0340(16) -0.0153(12) -0.0101(12) -0.0002(11) C49 0.0254(15) 0.0248(14) 0.0285(16) -0.0095(12) -0.0031(12) -0.0008(12) C50 0.0331(16) 0.0239(14) 0.0380(17) -0.0120(13) -0.0160(14) -0.0017(13) C51 0.0239(14) 0.0198(13) 0.0291(15) -0.0097(12) -0.0088(12) -0.0010(11) N52 0.0236(13) 0.0249(12) 0.0462(16) -0.0160(12) -0.0130(12) 0.0040(10) C53 0.0366(18) 0.0327(16) 0.0439(19) -0.0147(15) -0.0246(15) 0.0062(14) C54 0.0322(16) 0.0293(15) 0.0307(16) -0.0157(13) -0.0111(13) 0.0053(13) C55 0.0281(15) 0.0287(15) 0.0359(17) -0.0165(13) -0.0095(13) -0.0001(13) N56 0.0280(13) 0.0222(12) 0.0500(17) -0.0165(12) -0.0194(12) 0.0052(10) C57 0.0210(14) 0.0207(13) 0.0320(16) -0.0116(12) -0.0097(12) -0.0008(11) C58 0.0225(13) 0.0175(13) 0.0337(16) -0.0095(12) -0.0103(12) -0.0040(11) C59 0.0173(12) 0.0198(13) 0.0309(15) -0.0095(12) -0.0082(11) -0.0023(11) C60 0.0224(15) 0.0304(16) 0.0413(19) -0.0171(14) -0.0069(13) 0.0044(13) C61 0.0214(13) 0.0236(13) 0.0359(16) -0.0158(12) -0.0097(12) -0.0020(11) C62 0.0157(12) 0.0163(12) 0.0262(14) -0.0077(11) -0.0063(11) -0.0010(10) N63 0.0177(12) 0.0280(13) 0.0474(16) -0.0207(12) -0.0084(11) 0.0036(10) C64 0.0171(12) 0.0212(12) 0.0235(14) -0.0077(11) -0.0061(10) -0.0030(10) C65 0.0315(17) 0.0398(18) 0.0374(19) -0.0143(15) -0.0113(14) 0.0006(14) C66 0.0214(15) 0.0458(19) 0.0374(18) -0.0213(16) -0.0042(13) 0.0009(14) C67 0.0183(13) 0.0245(13) 0.0225(14) -0.0071(11) -0.0072(11) -0.0027(11) C68 0.0233(14) 0.0228(14) 0.0394(17) -0.0094(13) -0.0148(13) -0.0001(12) C69 0.0285(15) 0.0254(14) 0.0355(17) -0.0121(13) -0.0178(13) 0.0018(12) C70 0.0290(16) 0.0348(17) 0.050(2) -0.0236(16) -0.0074(15) 0.0015(14) C71 0.0246(14) 0.0233(13) 0.0306(16) -0.0128(12) -0.0104(12) 0.0010(12) C72 0.0182(13) 0.0212(13) 0.0222(14) -0.0078(11) -0.0072(11) -0.0017(11) C73 0.0391(19) 0.0335(17) 0.057(2) -0.0135(17) -0.0277(18) 0.0044(15) C74 0.0257(14) 0.0311(15) 0.0286(16) -0.0098(12) -0.0105(12) -0.0095(12) C75 0.0331(16) 0.0339(16) 0.0364(18) -0.0139(14) -0.0133(14) -0.0080(14) C76 0.053(2) 0.0375(18) 0.0318(18) -0.0124(15) -0.0189(16) 0.0147(16) C77 0.0378(19) 0.0408(19) 0.0380(19) -0.0135(16) -0.0074(15) 0.0070(16) C78 0.062(3) 0.0396(19) 0.046(2) -0.0165(17) -0.036(2) 0.0232(18) C79 0.0318(16) 0.0213(13) 0.0244(15) -0.0085(11) -0.0076(12) -0.0052(12) C80 0.0342(17) 0.0229(15) 0.049(2) -0.0089(14) -0.0218(15) -0.0004(13) C81 0.0283(16) 0.0389(17) 0.0426(19) -0.0230(16) -0.0079(14) 0.0019(14) C82 0.035(2) 0.060(2) 0.034(2) 0.0082(18) -0.0006(16) 0.0222(18) C83 0.0349(19) 0.053(2) 0.052(2) -0.029(2) -0.0018(17) 0.0115(17) C84 0.038(2) 0.066(3) 0.048(2) -0.005(2) 0.0024(18) 0.024(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.16837(10) 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 . H12 . 0.853 no O1 . H11 . 0.832 no O2 . C24 . 1.365(3) yes O2 . H21 . 0.824 no O3 . C13 . 1.359(3) yes O3 . H31 . 0.815 no O4 . C64 . 1.359(3) yes O4 . H41 . 0.820 no O5 . C72 . 1.358(3) yes O5 . H51 . 0.827 no O6 . H62 . 0.834 no O6 . H61 . 0.818 no O7 . C67 . 1.362(3) yes O7 . H71 . 0.837 no O8 . C26 . 1.368(3) yes O8 . H81 . 0.817 no O9 . C20 . 1.369(3) yes O9 . H91 . 0.817 no C10 . C15 . 1.489(4) yes C10 . C25 . 1.390(4) yes C10 . C49 . 1.395(4) yes O11 . C23 . 1.372(3) yes O11 . H111 . 0.810 no C12 . C42 . 1.390(4) yes C12 . C43 . 1.386(4) yes C12 . C62 . 1.495(3) yes C13 . C37 . 1.390(4) yes C13 . C67 . 1.405(4) yes N14 . C66 . 1.338(4) yes N14 . C69 . 1.337(4) yes C15 . C21 . 1.391(4) yes C15 . C54 . 1.392(4) yes O16 . C27 . 1.363(3) yes O16 . H161 . 0.810 no N17 . C70 . 1.336(4) yes N17 . C80 . 1.336(4) yes N18 . C45 . 1.334(4) yes N18 . C68 . 1.336(4) yes C19 . C23 . 1.389(4) yes C19 . C75 . 1.389(4) yes C19 . H191 . 0.952 no C20 . C64 . 1.405(4) yes C20 . C79 . 1.381(4) yes C21 . C36 . 1.393(4) yes C21 . H211 . 0.941 no C22 . C24 . 1.391(4) yes C22 . C74 . 1.393(4) yes C22 . H221 . 0.944 no C23 . C67 . 1.397(4) yes C24 . C64 . 1.398(4) yes C25 . C30 . 1.384(4) yes C25 . H251 . 0.935 no C26 . C35 . 1.381(4) yes C26 . C72 . 1.396(4) yes C27 . C39 . 1.393(4) yes C27 . C72 . 1.399(4) yes C28 . C44 . 1.389(4) yes C28 . C48 . 1.395(4) yes C28 . H281 . 0.957 no O29 . H292 . 0.812 no O29 . H291 . 0.809 no C30 . N63 . 1.342(4) yes C30 . H301 . 0.944 no C31 . C42 . 1.387(4) yes C31 . N56 . 1.337(4) yes C31 . H311 . 0.949 no N32 . C44 . 1.337(4) yes N32 . C81 . 1.331(4) yes C33 . C35 . 1.392(4) yes C33 . C39 . 1.389(4) yes C33 . H331 . 0.931 no C34 . C59 . 1.393(4) yes C34 . C66 . 1.381(4) yes C34 . H341 . 0.962 no C35 . H351 . 0.936 no C36 . N52 . 1.331(4) yes C36 . H361 . 0.933 no C37 . C75 . 1.385(4) yes C37 . H371 . 0.933 no N38 . C73 . 1.324(5) yes N38 . C83 . 1.328(5) yes C39 . H391 . 0.968 no C40 . C48 . 1.396(4) yes C40 . C81 . 1.392(4) yes C40 . H401 . 0.939 no N41 . C78 . 1.330(5) yes N41 . C84 . 1.298(5) yes C42 . H421 . 0.930 no C43 . C60 . 1.390(4) yes C43 . H431 . 0.953 no C44 . H441 . 0.940 no C45 . C46 . 1.395(4) yes C45 . H451 . 0.944 no C46 . C62 . 1.393(4) yes C46 . H461 . 0.951 no C47 . C49 . 1.384(4) yes C47 . N63 . 1.337(4) yes C47 . H471 . 0.947 no C48 . C58 . 1.491(4) yes C49 . H491 . 0.948 no C50 . C58 . 1.390(4) yes C50 . C80 . 1.383(4) yes C50 . H501 . 0.947 no C51 . C62 . 1.391(4) yes C51 . C68 . 1.388(4) yes C51 . H511 . 0.949 no N52 . C53 . 1.337(4) yes C53 . C54 . 1.385(4) yes C53 . H531 . 0.940 no C54 . H541 . 0.966 no C55 . C58 . 1.394(4) yes C55 . C70 . 1.381(4) yes C55 . H551 . 0.957 no N56 . C60 . 1.334(4) yes C57 . C59 . 1.494(4) yes C57 . C76 . 1.380(4) yes C57 . C82 . 1.360(5) yes C59 . C71 . 1.395(4) yes C60 . H601 . 0.942 no C61 . C61 2_756 1.488(5) yes C61 . C65 . 1.386(4) yes C61 . C77 . 1.386(5) yes C65 . C73 . 1.377(5) yes C65 . H651 . 0.914 no C66 . H661 . 0.945 no C68 . H681 . 0.937 no C69 . C71 . 1.390(4) yes C69 . H691 . 0.934 no C70 . H701 . 0.943 no C71 . H711 . 0.934 no C73 . H731 . 0.921 no C74 . C79 . 1.394(4) yes C74 . H741 . 0.946 no C75 . H751 . 0.942 no C76 . C78 . 1.393(5) yes C76 . H761 . 0.931 no C77 . C83 . 1.390(5) yes C77 . H771 . 0.923 no C78 . H781 . 0.929 no C79 . H791 . 0.964 no C80 . H801 . 0.941 no C81 . H811 . 0.917 no C82 . C84 . 1.391(5) yes C82 . H821 . 0.914 no C83 . H831 . 0.951 no C84 . H841 . 0.940 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 H12 . O1 . H11 . 108.2 no C24 . O2 . H21 . 106.4 no C13 . O3 . H31 . 102.8 no C64 . O4 . H41 . 117.4 no C72 . O5 . H51 . 117.3 no H62 . O6 . H61 . 108.9 no C67 . O7 . H71 . 110.7 no C26 . O8 . H81 . 111.2 no C20 . O9 . H91 . 107.4 no C15 . C10 . C25 . 121.9(2) yes C15 . C10 . C49 . 120.9(3) yes C25 . C10 . C49 . 117.2(2) yes C23 . O11 . H111 . 108.9 no C42 . C12 . C43 . 117.8(2) yes C42 . C12 . C62 . 121.1(2) yes C43 . C12 . C62 . 121.1(2) yes O3 . C13 . C37 . 124.8(2) yes O3 . C13 . C67 . 115.8(2) yes C37 . C13 . C67 . 119.4(3) yes C66 . N14 . C69 . 117.0(3) yes C10 . C15 . C21 . 121.5(3) yes C10 . C15 . C54 . 121.3(3) yes C21 . C15 . C54 . 117.1(2) yes C27 . O16 . H161 . 107.5 no C70 . N17 . C80 . 116.7(3) yes C45 . N18 . C68 . 117.0(2) yes C23 . C19 . C75 . 119.2(3) yes C23 . C19 . H191 . 119.8 no C75 . C19 . H191 . 121.0 no O9 . C20 . C64 . 114.8(2) yes O9 . C20 . C79 . 124.9(2) yes C64 . C20 . C79 . 120.2(3) yes C15 . C21 . C36 . 118.6(3) yes C15 . C21 . H211 . 121.6 no C36 . C21 . H211 . 119.8 no C24 . C22 . C74 . 119.4(3) yes C24 . C22 . H221 . 120.0 no C74 . C22 . H221 . 120.5 no C19 . C23 . O11 . 124.6(3) yes C19 . C23 . C67 . 120.5(3) yes O11 . C23 . C67 . 114.8(3) yes C22 . C24 . O2 . 124.4(2) yes C22 . C24 . C64 . 120.3(3) yes O2 . C24 . C64 . 115.3(2) yes C10 . C25 . C30 . 119.5(3) yes C10 . C25 . H251 . 122.0 no C30 . C25 . H251 . 118.5 no O8 . C26 . C35 . 124.8(2) yes O8 . C26 . C72 . 114.5(2) yes C35 . C26 . C72 . 120.7(3) yes O16 . C27 . C39 . 123.8(2) yes O16 . C27 . C72 . 116.1(2) yes C39 . C27 . C72 . 120.1(3) yes C44 . C28 . C48 . 118.9(3) yes C44 . C28 . H281 . 120.8 no C48 . C28 . H281 . 120.3 no H292 . O29 . H291 . 114.3 no C25 . C30 . N63 . 123.8(3) yes C25 . C30 . H301 . 117.7 no N63 . C30 . H301 . 118.5 no C42 . C31 . N56 . 123.6(3) yes C42 . C31 . H311 . 118.3 no N56 . C31 . H311 . 118.1 no C44 . N32 . C81 . 116.9(3) yes C35 . C33 . C39 . 120.8(3) yes C35 . C33 . H331 . 118.7 no C39 . C33 . H331 . 120.4 no C59 . C34 . C66 . 119.7(3) yes C59 . C34 . H341 . 119.0 no C66 . C34 . H341 . 121.3 no C33 . C35 . C26 . 119.5(3) yes C33 . C35 . H351 . 119.5 no C26 . C35 . H351 . 121.0 no C21 . C36 . N52 . 124.5(3) yes C21 . C36 . H361 . 119.1 no N52 . C36 . H361 . 116.4 no C13 . C37 . C75 . 120.1(3) yes C13 . C37 . H371 . 118.4 no C75 . C37 . H371 . 121.5 no C73 . N38 . C83 . 115.9(3) yes C27 . C39 . C33 . 119.5(3) yes C27 . C39 . H391 . 120.7 no C33 . C39 . H391 . 119.8 no C48 . C40 . C81 . 118.9(3) yes C48 . C40 . H401 . 121.6 no C81 . C40 . H401 . 119.5 no C78 . N41 . C84 . 115.5(3) yes C12 . C42 . C31 . 119.1(3) yes C12 . C42 . H421 . 120.6 no C31 . C42 . H421 . 120.3 no C12 . C43 . C60 . 118.9(3) yes C12 . C43 . H431 . 121.6 no C60 . C43 . H431 . 119.6 no C28 . C44 . N32 . 123.9(3) yes C28 . C44 . H441 . 118.0 no N32 . C44 . H441 . 118.1 no N18 . C45 . C46 . 124.0(3) yes N18 . C45 . H451 . 116.4 no C46 . C45 . H451 . 119.6 no C45 . C46 . C62 . 118.3(3) yes C45 . C46 . H461 . 120.2 no C62 . C46 . H461 . 121.5 no C49 . C47 . N63 . 124.0(3) yes C49 . C47 . H471 . 120.7 no N63 . C47 . H471 . 115.3 no C40 . C48 . C28 . 117.6(3) yes C40 . C48 . C58 . 121.5(3) yes C28 . C48 . C58 . 120.9(3) yes C10 . C49 . C47 . 119.2(3) yes C10 . C49 . H491 . 120.9 no C47 . C49 . H491 . 120.0 no C58 . C50 . C80 . 119.1(3) yes C58 . C50 . H501 . 122.4 no C80 . C50 . H501 . 118.5 no C62 . C51 . C68 . 119.1(3) yes C62 . C51 . H511 . 120.6 no C68 . C51 . H511 . 120.3 no C36 . N52 . C53 . 116.6(3) yes N52 . C53 . C54 . 123.3(3) yes N52 . C53 . H531 . 118.6 no C54 . C53 . H531 . 118.1 no C15 . C54 . C53 . 119.9(3) yes C15 . C54 . H541 . 120.1 no C53 . C54 . H541 . 120.0 no C58 . C55 . C70 . 118.9(3) yes C58 . C55 . H551 . 119.9 no C70 . C55 . H551 . 121.2 no C31 . N56 . C60 . 116.8(3) yes C59 . C57 . C76 . 121.6(3) yes C59 . C57 . C82 . 122.1(3) yes C76 . C57 . C82 . 116.4(3) yes C48 . C58 . C55 . 121.0(3) yes C48 . C58 . C50 . 121.5(3) yes C55 . C58 . C50 . 117.5(3) yes C57 . C59 . C34 . 121.5(3) yes C57 . C59 . C71 . 121.2(3) yes C34 . C59 . C71 . 117.2(3) yes C43 . C60 . N56 . 123.9(3) yes C43 . C60 . H601 . 118.3 no N56 . C60 . H601 . 117.8 no C61 2_756 C61 . C65 . 122.1(3) yes C61 2_756 C61 . C77 . 121.8(3) yes C65 . C61 . C77 . 116.2(3) yes C12 . C62 . C46 . 120.7(2) yes C12 . C62 . C51 . 121.3(2) yes C46 . C62 . C51 . 118.0(2) yes C30 . N63 . C47 . 116.3(2) yes C20 . C64 . C24 . 119.5(2) yes C20 . C64 . O4 . 116.8(2) yes C24 . C64 . O4 . 123.7(2) yes C61 . C65 . C73 . 120.1(3) yes C61 . C65 . H651 . 120.1 no C73 . C65 . H651 . 119.8 no C34 . C66 . N14 . 123.5(3) yes C34 . C66 . H661 . 117.7 no N14 . C66 . H661 . 118.8 no C13 . C67 . C23 . 119.7(3) yes C13 . C67 . O7 . 122.9(2) yes C23 . C67 . O7 . 117.4(2) yes C51 . C68 . N18 . 123.5(3) yes C51 . C68 . H681 . 119.0 no N18 . C68 . H681 . 117.5 no N14 . C69 . C71 . 123.6(3) yes N14 . C69 . H691 . 118.2 no C71 . C69 . H691 . 118.3 no C55 . C70 . N17 . 124.0(3) yes C55 . C70 . H701 . 118.1 no N17 . C70 . H701 . 117.9 no C59 . C71 . C69 . 119.0(3) yes C59 . C71 . H711 . 123.8 no C69 . C71 . H711 . 117.2 no C27 . C72 . C26 . 119.4(2) yes C27 . C72 . O5 . 123.1(2) yes C26 . C72 . O5 . 117.4(2) yes C65 . C73 . N38 . 124.2(3) yes C65 . C73 . H731 . 117.1 no N38 . C73 . H731 . 118.7 no C22 . C74 . C79 . 120.8(3) yes C22 . C74 . H741 . 118.5 no C79 . C74 . H741 . 120.7 no C19 . C75 . C37 . 121.0(3) yes C19 . C75 . H751 . 118.5 no C37 . C75 . H751 . 120.5 no C57 . C76 . C78 . 119.3(3) yes C57 . C76 . H761 . 120.9 no C78 . C76 . H761 . 119.8 no C61 . C77 . C83 . 119.4(3) yes C61 . C77 . H771 . 120.7 no C83 . C77 . H771 . 119.9 no C76 . C78 . N41 . 124.1(3) yes C76 . C78 . H781 . 119.2 no N41 . C78 . H781 . 116.7 no C74 . C79 . C20 . 119.8(3) yes C74 . C79 . H791 . 120.5 no C20 . C79 . H791 . 119.7 no C50 . C80 . N17 . 123.8(3) yes C50 . C80 . H801 . 118.1 no N17 . C80 . H801 . 118.1 no C40 . C81 . N32 . 123.9(3) yes C40 . C81 . H811 . 119.0 no N32 . C81 . H811 . 117.1 no C57 . C82 . C84 . 120.0(3) yes C57 . C82 . H821 . 121.7 no C84 . C82 . H821 . 118.3 no C77 . C83 . N38 . 124.2(4) yes C77 . C83 . H831 . 117.6 no N38 . C83 . H831 . 118.2 no C82 . C84 . N41 . 124.8(4) yes C82 . C84 . H841 . 119.6 no N41 . C84 . H841 . 115.6 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 C28 . H281 . O7 2_666 162 0.96 2.48 3.407(5) yes C69 . H691 . O6 2_566 137 0.93 2.60 3.339(5) yes O5 . H51 . O1 . 166 0.83 1.77 2.582(5) yes O9 . H91 . N52 1_545 145 0.82 2.01 2.719(5) yes O16 . H161 . N18 2_656 164 0.81 1.95 2.741(5) yes O8 . H81 . N56 2_566 149 0.82 1.97 2.708(5) yes O4 . H41 . O6 . 165 0.82 1.78 2.579(5) yes O2 . H21 . N63 1_455 160 0.82 1.94 2.727(5) yes O3 . H31 . N14 . 158 0.82 1.96 2.733(5) yes O7 . H71 . O29 2_666 159 0.84 1.77 2.570(5) yes O11 . H111 . N41 1_645 150 0.81 2.00 2.729(5) yes O1 . H12 . N17 1_545 156 0.85 1.97 2.775(5) yes O29 . H292 . O7 . 131 0.81 2.29 2.891(5) yes O29 . H292 . O11 . 159 0.81 2.23 3.000(5) yes O29 . H291 . N38 . 175 0.81 1.98 2.791(5) yes O6 . H62 . O5 . 137 0.83 2.26 2.919(5) yes O6 . H62 . O8 . 148 0.83 2.18 2.921(5) yes O1 . H11 . O4 . 133 0.83 2.29 2.923(5) yes O1 . H11 . O9 . 156 0.83 2.18 2.954(5) yes O6 . H61 . N32 1_455 129 0.82 2.17 2.764(5) yes data_1 _database_code_depnum_ccdc_archive 'CCDC 881429' #TrackingRef '11198_web_deposit_cif_file_0_MikelisV.veidis_1336638097.Iphenpyrogallol.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 7.3010(15) _cell_length_b 16.518(3) _cell_length_c 24.294(3) _cell_angle_alpha 90 _cell_angle_beta 98.53(3) _cell_angle_gamma 90 _cell_volume 2897.4(9) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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' _cell_formula_units_Z 4 # Given Formula = C32 H28 N2 O6 # Dc = 1.23 Fooo = 1280.00 Mu = 0.86 M = 536.58 # Found Formula = C36 H28 N4 O6 # Dc = 1.40 FOOO = 1280.00 Mu = 0.97 M = 612.64 _chemical_formula_sum 'C36 H28 N4 O6' _chemical_formula_moiety 'C36 H28 N4 O6' _chemical_compound_source ? _chemical_formula_weight 612.64 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_min 0.220 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_max 0.300 _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.097 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type none # 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_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _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 38094 _reflns_number_total 6605 _diffrn_reflns_av_R_equivalents 0.054 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 6605 # Theoretical number of reflections is about 13305 _diffrn_reflns_theta_min 2.096 _diffrn_reflns_theta_max 27.510 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.034 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 0 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 31 _oxford_diffrn_Wilson_B_factor 2.17 _oxford_diffrn_Wilson_scale 50.58 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.29 _refine_diff_density_max 0.85 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 3498 _refine_ls_number_restraints 0 _refine_ls_number_parameters 416 _oxford_refine_ls_R_factor_ref 0.0528 _refine_ls_wR_factor_ref 0.0928 _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_shift/su_max 0.0001910 _refine_ls_shift/su_mean 0.0000158 # The values computed with all filters except I/sigma _oxford_reflns_number_all 6598 _refine_ls_R_factor_all 0.1105 _refine_ls_wR_factor_all 0.1087 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3789 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_gt 0.0956 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed # WARNING. The IUCr will not accept Unit Weights _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Quasi-Unit weights W = 1.0 or 1./2F ; # Insert your own references if required - in alphabetical order 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 0.0217(3) 0.01644(15) 0.36328(10) 0.0362 1.0000 Uani . . . . . . C2 C 0.1354(5) -0.0385(2) 0.34290(13) 0.0257 1.0000 Uani . . . . . . C3 C 0.3162(5) -0.0202(2) 0.33639(14) 0.0281 1.0000 Uani . . . . . . O4 O 0.4032(3) 0.05185(16) 0.35054(12) 0.0430 1.0000 Uani . . . . . . C5 C 0.4247(5) -0.0801(2) 0.31651(15) 0.0306 1.0000 Uani . . . . . . O6 O 0.6051(4) -0.06428(19) 0.31261(14) 0.0623 1.0000 Uani . . . . . . C7 C 0.3552(5) -0.1552(2) 0.30172(14) 0.0330 1.0000 Uani . . . . . . C8 C 0.1724(5) -0.1721(2) 0.30726(14) 0.0332 1.0000 Uani . . . . . . C9 C 0.0615(5) -0.1145(2) 0.32742(13) 0.0308 1.0000 Uani . . . . . . O10 O 0.1370(3) 0.60082(16) 0.42128(10) 0.0355 1.0000 Uani . . . . . . C11 C 0.2079(5) 0.6077(2) 0.37253(13) 0.0262 1.0000 Uani . . . . . . C12 C 0.3891(5) 0.63139(19) 0.37084(13) 0.0238 1.0000 Uani . . . . . . O13 O 0.5154(3) 0.64837(14) 0.41704(9) 0.0298 1.0000 Uani . . . . . . C14 C 0.4544(5) 0.6356(2) 0.32018(14) 0.0267 1.0000 Uani . . . . . . O15 O 0.6343(3) 0.65933(16) 0.31954(10) 0.0385 1.0000 Uani . . . . . . C16 C 0.3416(5) 0.6166(2) 0.27090(14) 0.0356 1.0000 Uani . . . . . . C17 C 0.1610(5) 0.5940(2) 0.27281(14) 0.0373 1.0000 Uani . . . . . . C18 C 0.0933(5) 0.5900(2) 0.32318(15) 0.0332 1.0000 Uani . . . . . . N19 N 0.6639(4) 0.38831(16) 0.47105(11) 0.0266 1.0000 Uani . . . . . . C20 C 0.6786(4) 0.3207(2) 0.44056(13) 0.0219 1.0000 Uani . . . . . . C21 C 0.7110(4) 0.3230(2) 0.38490(12) 0.0228 1.0000 Uani . . . . . . C22 C 0.7197(5) 0.3994(2) 0.35994(14) 0.0302 1.0000 Uani . . . . . . C23 C 0.6961(5) 0.4675(2) 0.39001(15) 0.0337 1.0000 Uani . . . . . . C24 C 0.6703(5) 0.4589(2) 0.44552(15) 0.0321 1.0000 Uani . . . . . . C25 C 0.7374(4) 0.2491(2) 0.35606(13) 0.0255 1.0000 Uani . . . . . . C26 C 0.7263(4) 0.1767(2) 0.38093(12) 0.0233 1.0000 Uani . . . . . . C27 C 0.6848(4) 0.1715(2) 0.43674(13) 0.0217 1.0000 Uani . . . . . . C28 C 0.6621(4) 0.2426(2) 0.46668(13) 0.0213 1.0000 Uani . . . . . . N29 N 0.6210(4) 0.24117(17) 0.51964(10) 0.0228 1.0000 Uani . . . . . . C30 C 0.6058(4) 0.1695(2) 0.54317(13) 0.0260 1.0000 Uani . . . . . . C31 C 0.6282(5) 0.0962(2) 0.51664(14) 0.0278 1.0000 Uani . . . . . . C32 C 0.6662(5) 0.0968(2) 0.46320(13) 0.0259 1.0000 Uani . . . . . . N33 N 0.2323(4) 0.19949(18) 0.34657(11) 0.0299 1.0000 Uani . . . . . . C34 C 0.2034(4) 0.2485(2) 0.38937(13) 0.0234 1.0000 Uani . . . . . . C35 C 0.1701(4) 0.2113(2) 0.44070(13) 0.0215 1.0000 Uani . . . . . . N36 N 0.1625(4) 0.12940(16) 0.44316(11) 0.0246 1.0000 Uani . . . . . . C37 C 0.1326(5) 0.0968(2) 0.49067(15) 0.0323 1.0000 Uani . . . . . . C38 C 0.1071(5) 0.1401(3) 0.53773(15) 0.0370 1.0000 Uani . . . . . . C39 C 0.1097(5) 0.2222(2) 0.53519(14) 0.0345 1.0000 Uani . . . . . . C40 C 0.1428(4) 0.2612(2) 0.48585(14) 0.0259 1.0000 Uani . . . . . . C41 C 0.1441(5) 0.3469(2) 0.48013(16) 0.0342 1.0000 Uani . . . . . . C42 C 0.1723(5) 0.3817(2) 0.43235(16) 0.0341 1.0000 Uani . . . . . . C43 C 0.2031(4) 0.3338(2) 0.38532(14) 0.0274 1.0000 Uani . . . . . . C44 C 0.2294(5) 0.3680(2) 0.33411(17) 0.0393 1.0000 Uani . . . . . . C45 C 0.2552(5) 0.3185(3) 0.29130(16) 0.0434 1.0000 Uani . . . . . . C46 C 0.2563(5) 0.2348(3) 0.29906(15) 0.0390 1.0000 Uani . . . . . . H71 H 0.4324 -0.1948 0.2879 0.0399 1.0000 Uiso R . . . . . H81 H 0.1199 -0.2244 0.2975 0.0403 1.0000 Uiso R . . . . . H91 H -0.0728 -0.1326 0.3335 0.0308 1.0000 Uiso R . . . . . H161 H 0.3876 0.6187 0.2371 0.0425 1.0000 Uiso R . . . . . H171 H 0.0850 0.5809 0.2397 0.0452 1.0000 Uiso R . . . . . H181 H -0.0352 0.5743 0.3248 0.0396 1.0000 Uiso R . . . . . H221 H 0.7448 0.4029 0.3221 0.0368 1.0000 Uiso R . . . . . H231 H 0.7012 0.5188 0.3747 0.0410 1.0000 Uiso R . . . . . H241 H 0.6582 0.5065 0.4663 0.0392 1.0000 Uiso R . . . . . H251 H 0.7637 0.2516 0.3191 0.0303 1.0000 Uiso R . . . . . H261 H 0.7458 0.1292 0.3622 0.0273 1.0000 Uiso R . . . . . H301 H 0.5789 0.1687 0.5801 0.0307 1.0000 Uiso R . . . . . H311 H 0.6198 0.0478 0.5351 0.0338 1.0000 Uiso R . . . . . H321 H 0.6782 0.0488 0.4438 0.0321 1.0000 Uiso R . . . . . H371 H 0.1294 0.0391 0.4919 0.0397 1.0000 Uiso R . . . . . H381 H 0.0887 0.1133 0.5703 0.0449 1.0000 Uiso R . . . . . H391 H 0.0895 0.2536 0.5659 0.0418 1.0000 Uiso R . . . . . H411 H 0.1273 0.3791 0.5118 0.0408 1.0000 Uiso R . . . . . H421 H 0.1697 0.4387 0.4289 0.0412 1.0000 Uiso R . . . . . H441 H 0.2303 0.4247 0.3301 0.0483 1.0000 Uiso R . . . . . H451 H 0.2705 0.3395 0.2563 0.0535 1.0000 Uiso R . . . . . H461 H 0.2736 0.2002 0.2698 0.0463 1.0000 Uiso R . . . . . H151 H 0.6847 0.6680 0.3527 0.0584 1.0000 Uiso R . . . . . H131 H 0.4634 0.6768 0.4396 0.0453 1.0000 Uiso R . . . . . H11 H 0.0856 0.0511 0.3824 0.0554 1.0000 Uiso R . . . . . H101 H 0.2137 0.6032 0.4514 0.0549 1.0000 Uiso R . . . . . H41 H 0.3256 0.0893 0.3540 0.0657 1.0000 Uiso R . . . . . H61 H 0.6237 -0.0139 0.3211 0.0947 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 0.0276(14) 0.0356(15) 0.0461(15) -0.0153(12) 0.0075(11) 0.0015(11) C2 0.0287(19) 0.0290(19) 0.0190(16) -0.0023(14) 0.0022(13) 0.0044(15) C3 0.031(2) 0.0238(18) 0.0290(18) -0.0047(14) 0.0038(14) -0.0005(15) O4 0.0322(15) 0.0310(15) 0.0688(19) -0.0179(13) 0.0177(13) -0.0041(12) C5 0.029(2) 0.033(2) 0.0310(19) -0.0012(15) 0.0079(15) 0.0004(15) O6 0.0471(19) 0.053(2) 0.093(3) -0.0203(18) 0.0297(17) -0.0026(15) C7 0.043(2) 0.028(2) 0.0281(19) -0.0046(15) 0.0081(16) 0.0077(17) C8 0.046(2) 0.0265(19) 0.0281(18) -0.0044(15) 0.0072(15) -0.0071(17) C9 0.038(2) 0.030(2) 0.0237(17) -0.0056(15) 0.0030(15) -0.0022(16) O10 0.0360(15) 0.0441(16) 0.0287(13) -0.0048(12) 0.0124(11) -0.0063(12) C11 0.0313(19) 0.0208(17) 0.0277(18) -0.0017(14) 0.0079(14) 0.0018(15) C12 0.0305(18) 0.0205(17) 0.0206(16) -0.0014(13) 0.0040(13) 0.0052(14) O13 0.0324(14) 0.0356(15) 0.0219(12) -0.0056(10) 0.0058(10) 0.0026(11) C14 0.031(2) 0.0235(18) 0.0275(18) 0.0016(14) 0.0093(14) 0.0045(15) O15 0.0356(15) 0.0512(17) 0.0306(13) 0.0044(12) 0.0116(11) 0.0008(13) C16 0.047(2) 0.038(2) 0.0222(18) -0.0003(15) 0.0069(16) 0.0064(18) C17 0.047(2) 0.038(2) 0.0231(18) -0.0054(16) -0.0061(16) 0.0046(19) C18 0.033(2) 0.030(2) 0.036(2) -0.0036(16) 0.0031(16) -0.0020(16) N19 0.0319(16) 0.0213(15) 0.0280(15) 0.0004(12) 0.0083(12) 0.0002(13) C20 0.0168(16) 0.0249(18) 0.0236(16) 0.0003(14) 0.0015(12) 0.0002(14) C21 0.0209(17) 0.0271(18) 0.0195(16) 0.0026(14) 0.0000(12) 0.0003(14) C22 0.0283(19) 0.036(2) 0.0261(18) 0.0081(16) 0.0029(14) 0.0001(16) C23 0.038(2) 0.0225(19) 0.041(2) 0.0094(16) 0.0065(16) 0.0015(16) C24 0.036(2) 0.0262(19) 0.035(2) -0.0031(16) 0.0077(16) 0.0003(16) C25 0.0248(18) 0.034(2) 0.0178(16) -0.0012(14) 0.0026(13) -0.0012(16) C26 0.0231(17) 0.0267(18) 0.0195(16) -0.0056(14) 0.0018(12) 0.0018(14) C27 0.0185(17) 0.0230(17) 0.0228(16) -0.0001(14) 0.0004(12) -0.0012(14) C28 0.0187(16) 0.0233(18) 0.0211(17) 0.0003(13) 0.0003(13) -0.0014(13) N29 0.0252(15) 0.0247(15) 0.0190(14) -0.0012(11) 0.0048(11) -0.0006(12) C30 0.0260(18) 0.0307(19) 0.0223(16) 0.0038(15) 0.0067(13) -0.0010(15) C31 0.0301(19) 0.0228(18) 0.0300(19) 0.0056(15) 0.0031(14) -0.0020(15) C32 0.0276(19) 0.0218(18) 0.0274(18) -0.0030(14) 0.0011(14) -0.0006(15) N33 0.0283(16) 0.0381(18) 0.0248(15) 0.0008(13) 0.0094(12) 0.0021(13) C34 0.0165(16) 0.0285(18) 0.0249(17) 0.0028(14) 0.0016(12) -0.0008(14) C35 0.0146(16) 0.0279(18) 0.0220(16) 0.0016(14) 0.0029(12) 0.0007(14) N36 0.0226(15) 0.0225(15) 0.0298(16) 0.0040(12) 0.0077(12) 0.0011(12) C37 0.0248(19) 0.031(2) 0.042(2) 0.0133(17) 0.0077(16) 0.0032(16) C38 0.030(2) 0.056(3) 0.026(2) 0.0121(18) 0.0072(16) 0.0007(18) C39 0.026(2) 0.056(3) 0.0222(18) -0.0086(17) 0.0039(15) -0.0003(18) C40 0.0184(17) 0.033(2) 0.0258(17) -0.0048(15) 0.0021(13) -0.0025(15) C41 0.031(2) 0.031(2) 0.041(2) -0.0128(17) 0.0047(16) -0.0026(16) C42 0.028(2) 0.0192(18) 0.054(2) -0.0051(17) 0.0028(17) -0.0018(15) C43 0.0175(17) 0.0266(19) 0.0373(19) 0.0066(16) 0.0015(14) -0.0002(15) C44 0.028(2) 0.037(2) 0.052(3) 0.0191(19) 0.0044(18) 0.0017(17) C45 0.031(2) 0.063(3) 0.037(2) 0.027(2) 0.0065(16) 0.005(2) C46 0.032(2) 0.058(3) 0.0277(19) 0.0015(18) 0.0077(16) 0.0039(19) _refine_ls_extinction_coef 174(13) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.14060(7) 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 . C2 . 1.371(4) yes O1 . H11 . 0.835 no C2 . C3 . 1.386(5) yes C2 . C9 . 1.397(5) yes C3 . O4 . 1.368(4) yes C3 . C5 . 1.398(5) yes O4 . H41 . 0.851 no C5 . O6 . 1.360(4) yes C5 . C7 . 1.367(5) yes O6 . H61 . 0.863 no C7 . C8 . 1.390(5) yes C7 . H71 . 0.956 no C8 . C9 . 1.384(5) yes C8 . H81 . 0.961 no C9 . H91 . 1.056 no O10 . C11 . 1.366(4) yes O10 . H101 . 0.853 no C11 . C12 . 1.386(5) yes C11 . C18 . 1.388(5) yes C12 . O13 . 1.372(4) yes C12 . C14 . 1.386(4) yes O13 . H131 . 0.851 no C14 . O15 . 1.373(4) yes C14 . C16 . 1.385(5) yes O15 . H151 . 0.846 no C16 . C17 . 1.378(5) yes C16 . H161 . 0.933 no C17 . C18 . 1.388(5) yes C17 . H171 . 0.934 no C18 . H181 . 0.980 no N19 . C20 . 1.354(4) yes N19 . C24 . 1.325(4) yes C20 . C21 . 1.407(4) yes C20 . C28 . 1.450(5) yes C21 . C22 . 1.406(5) yes C21 . C25 . 1.435(5) yes C22 . C23 . 1.366(5) yes C22 . H221 . 0.966 no C23 . C24 . 1.396(5) yes C23 . H231 . 0.928 no C24 . H241 . 0.945 no C25 . C26 . 1.347(5) yes C25 . H251 . 0.945 no C26 . C27 . 1.435(4) yes C26 . H261 . 0.929 no C27 . C28 . 1.404(4) yes C27 . C32 . 1.407(5) yes C28 . N29 . 1.364(4) yes N29 . C30 . 1.326(4) yes C30 . C31 . 1.392(5) yes C30 . H301 . 0.946 no C31 . C32 . 1.367(5) yes C31 . H311 . 0.924 no C32 . H321 . 0.933 no N33 . C34 . 1.358(4) yes N33 . C46 . 1.328(4) yes C34 . C35 . 1.442(4) yes C34 . C43 . 1.413(5) yes C35 . N36 . 1.356(4) yes C35 . C40 . 1.409(4) yes N36 . C37 . 1.321(4) yes C37 . C38 . 1.384(5) yes C37 . H371 . 0.954 no C38 . C39 . 1.359(5) yes C38 . H381 . 0.934 no C39 . C40 . 1.412(5) yes C39 . H391 . 0.938 no C40 . C41 . 1.424(5) yes C41 . C42 . 1.338(5) yes C41 . H411 . 0.959 no C42 . C43 . 1.435(5) yes C42 . H421 . 0.945 no C43 . C44 . 1.405(5) yes C44 . C45 . 1.358(6) yes C44 . H441 . 0.942 no C45 . C46 . 1.395(6) yes C45 . H451 . 0.939 no C46 . H461 . 0.936 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 . O1 . H11 . 109.7 no O1 . C2 . C3 . 122.4(3) yes O1 . C2 . C9 . 117.5(3) yes C3 . C2 . C9 . 120.1(3) yes C2 . C3 . O4 . 125.1(3) yes C2 . C3 . C5 . 118.9(3) yes O4 . C3 . C5 . 115.9(3) yes C3 . O4 . H41 . 111.4 no C3 . C5 . O6 . 119.5(3) yes C3 . C5 . C7 . 121.7(3) yes O6 . C5 . C7 . 118.8(3) yes C5 . O6 . H61 . 106.7 no C5 . C7 . C8 . 118.7(3) yes C5 . C7 . H71 . 119.9 no C8 . C7 . H71 . 121.4 no C7 . C8 . C9 . 121.1(3) yes C7 . C8 . H81 . 120.6 no C9 . C8 . H81 . 118.2 no C2 . C9 . C8 . 119.3(3) yes C2 . C9 . H91 . 123.2 no C8 . C9 . H91 . 117.3 no C11 . O10 . H101 . 117.0 no O10 . C11 . C12 . 122.3(3) yes O10 . C11 . C18 . 118.3(3) yes C12 . C11 . C18 . 119.3(3) yes C11 . C12 . O13 . 124.2(3) yes C11 . C12 . C14 . 119.7(3) yes O13 . C12 . C14 . 116.0(3) yes C12 . O13 . H131 . 109.2 no C12 . C14 . O15 . 118.7(3) yes C12 . C14 . C16 . 121.2(3) yes O15 . C14 . C16 . 120.1(3) yes C14 . O15 . H151 . 108.6 no C14 . C16 . C17 . 118.8(3) yes C14 . C16 . H161 . 120.5 no C17 . C16 . H161 . 120.7 no C16 . C17 . C18 . 120.7(3) yes C16 . C17 . H171 . 118.9 no C18 . C17 . H171 . 120.4 no C17 . C18 . C11 . 120.2(3) yes C17 . C18 . H181 . 121.2 no C11 . C18 . H181 . 118.6 no C20 . N19 . C24 . 117.3(3) yes N19 . C20 . C21 . 122.8(3) yes N19 . C20 . C28 . 118.4(3) yes C21 . C20 . C28 . 118.8(3) yes C20 . C21 . C22 . 117.7(3) yes C20 . C21 . C25 . 120.0(3) yes C22 . C21 . C25 . 122.4(3) yes C21 . C22 . C23 . 119.4(3) yes C21 . C22 . H221 . 119.4 no C23 . C22 . H221 . 121.2 no C22 . C23 . C24 . 118.5(3) yes C22 . C23 . H231 . 121.4 no C24 . C23 . H231 . 120.0 no C23 . C24 . N19 . 124.2(3) yes C23 . C24 . H241 . 117.8 no N19 . C24 . H241 . 118.1 no C21 . C25 . C26 . 121.0(3) yes C21 . C25 . H251 . 119.2 no C26 . C25 . H251 . 119.8 no C25 . C26 . C27 . 120.8(3) yes C25 . C26 . H261 . 120.5 no C27 . C26 . H261 . 118.7 no C26 . C27 . C28 . 119.8(3) yes C26 . C27 . C32 . 122.2(3) yes C28 . C27 . C32 . 118.0(3) yes C20 . C28 . C27 . 119.5(3) yes C20 . C28 . N29 . 118.2(3) yes C27 . C28 . N29 . 122.2(3) yes C28 . N29 . C30 . 117.8(3) yes N29 . C30 . C31 . 123.6(3) yes N29 . C30 . H301 . 117.6 no C31 . C30 . H301 . 118.8 no C30 . C31 . C32 . 119.2(3) yes C30 . C31 . H311 . 120.5 no C32 . C31 . H311 . 120.3 no C27 . C32 . C31 . 119.1(3) yes C27 . C32 . H321 . 119.4 no C31 . C32 . H321 . 121.4 no C34 . N33 . C46 . 117.3(3) yes N33 . C34 . C35 . 118.3(3) yes N33 . C34 . C43 . 122.7(3) yes C35 . C34 . C43 . 119.1(3) yes C34 . C35 . N36 . 118.4(3) yes C34 . C35 . C40 . 119.1(3) yes N36 . C35 . C40 . 122.5(3) yes C35 . N36 . C37 . 117.3(3) yes N36 . C37 . C38 . 124.8(3) yes N36 . C37 . H371 . 116.2 no C38 . C37 . H371 . 118.9 no C37 . C38 . C39 . 118.3(3) yes C37 . C38 . H381 . 120.6 no C39 . C38 . H381 . 121.2 no C38 . C39 . C40 . 119.9(3) yes C38 . C39 . H391 . 120.7 no C40 . C39 . H391 . 119.4 no C39 . C40 . C35 . 117.2(3) yes C39 . C40 . C41 . 122.7(3) yes C35 . C40 . C41 . 120.1(3) yes C40 . C41 . C42 . 121.1(3) yes C40 . C41 . H411 . 118.0 no C42 . C41 . H411 . 120.9 no C41 . C42 . C43 . 121.1(3) yes C41 . C42 . H421 . 120.1 no C43 . C42 . H421 . 118.8 no C42 . C43 . C34 . 119.6(3) yes C42 . C43 . C44 . 122.8(3) yes C34 . C43 . C44 . 117.6(3) yes C43 . C44 . C45 . 119.3(4) yes C43 . C44 . H441 . 119.6 no C45 . C44 . H441 . 121.1 no C44 . C45 . C46 . 119.5(3) yes C44 . C45 . H451 . 121.3 no C46 . C45 . H451 . 119.2 no C45 . C46 . N33 . 123.6(4) yes C45 . C46 . H461 . 120.1 no N33 . C46 . H461 . 116.2 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 C9 . H91 . O6 1_455 133.16(11) 1.056 2.590 3.401(5) yes C45 . H451 . O6 3_655 156.65(12) 0.939 2.570 3.453(5) yes C46 . H461 . O15 3_645 157.42(11) 0.936 2.460 3.343(5) yes O13 . H131 . N29 2_666 165.82(11) 0.851 1.839 2.672(5) yes O1 . H11 . N36 . 159.38(10) 0.835 1.980 2.777(5) yes O10 . H101 . N19 2_666 166.22(10) 0.853 1.968 2.803(5) yes O4 . H41 . N33 . 154.20(11) 0.851 1.943 2.735(5) yes _iucr_refine_instruction_details_constraints ; # # Punched on 25/04/12 at 11:44:01 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE O ( 1,X'S) H ( 11,X'S) RIDE O ( 4,X'S) H ( 41,X'S) RIDE O ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE O ( 10,X'S) H ( 101,X'S) RIDE O ( 13,X'S) H ( 131,X'S) RIDE O ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 32,X'S) H ( 321,X'S) RIDE C ( 37,X'S) H ( 371,X'S) RIDE C ( 38,X'S) H ( 381,X'S) RIDE C ( 39,X'S) H ( 391,X'S) RIDE C ( 41,X'S) H ( 411,X'S) RIDE C ( 42,X'S) H ( 421,X'S) RIDE C ( 44,X'S) H ( 441,X'S) RIDE C ( 45,X'S) H ( 451,X'S) RIDE C ( 46,X'S) H ( 461,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 25/04/12 at 11:44:01 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 0 1 2 x . 0 2 0 x . -2 1 4 x . -2 1 2 x . -4 0 6 x . 1 0 0 x . -6 1 10 x . data_1 _database_code_depnum_ccdc_archive 'CCDC 881432' #TrackingRef '11199_web_deposit_cif_file_0_MikelisV.veidis_1336639506.II phenathraline-pyrogallol.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 10.6419(3) _cell_length_b 12.6654(4) _cell_length_c 22.1187(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2981.25(15) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _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 x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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' _cell_formula_units_Z 8 # Given Formula = C18 H16 N2 O3 # Dc = 1.37 Fooo = 1280.00 Mu = 0.95 M = 308.34 # Found Formula = C18 H14 N2 O3 # Dc = 1.36 FOOO = 1280.00 Mu = 0.95 M = 306.32 _chemical_formula_sum 'C18 H14 N2 O3' _chemical_formula_moiety 'C18 H14 N2 O3' _chemical_compound_source ? _chemical_formula_weight 306.32 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_max 0.500 _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.095 # Sheldrick geometric approximatio 0.95 0.98 _exptl_absorpt_correction_type none # 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_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _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, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _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 6319 _reflns_number_total 3414 _diffrn_reflns_av_R_equivalents 0.068 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3414 # Theoretical number of reflections is about 6790 _diffrn_reflns_theta_min 1.841 _diffrn_reflns_theta_max 27.475 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.475 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 0 _reflns_limit_h_min 0 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 2.20 _oxford_diffrn_Wilson_scale 19.61 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.27 _refine_diff_density_max 0.27 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 1729 _refine_ls_number_restraints 0 _refine_ls_number_parameters 209 _oxford_refine_ls_R_factor_ref 0.0473 _refine_ls_wR_factor_ref 0.1134 _refine_ls_goodness_of_fit_ref 1.0000 _refine_ls_shift/su_max 0.0001594 _refine_ls_shift/su_mean 0.0000169 # The values computed with all filters except I/sigma _oxford_reflns_number_all 3413 _refine_ls_R_factor_all 0.1321 _refine_ls_wR_factor_all 0.2451 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2019 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_gt 0.1257 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed # WARNING. The IUCr will not accept Unit Weights _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Quasi-Unit weights W = 1.0 or 1./2F ; # Insert your own references if required - in alphabetical order 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 0.7856(2) 0.6581(2) 0.35431(12) 0.0323 1.0000 Uani . . . . . . C2 C 0.8584(3) 0.5870(3) 0.32284(16) 0.0251 1.0000 Uani . . . . . . C3 C 0.9570(4) 0.6257(3) 0.28818(17) 0.0291 1.0000 Uani . . . . . . C4 C 1.0319(4) 0.5568(3) 0.25614(18) 0.0310 1.0000 Uani . . . . . . C5 C 1.0103(4) 0.4492(3) 0.25763(18) 0.0307 1.0000 Uani . . . . . . C6 C 0.9111(4) 0.4111(3) 0.29137(16) 0.0265 1.0000 Uani . . . . . . C7 C 0.8356(3) 0.4792(3) 0.32489(16) 0.0241 1.0000 Uani . . . . . . O8 O 0.7362(2) 0.4357(2) 0.35620(11) 0.0297 1.0000 Uani . . . . . . O9 O 0.8862(3) 0.3053(2) 0.29136(13) 0.0392 1.0000 Uani . . . . . . N10 N 0.7688(3) 0.4940(3) 0.47468(14) 0.0272 1.0000 Uani . . . . . . C11 C 0.6940(3) 0.5485(3) 0.51362(16) 0.0254 1.0000 Uani . . . . . . C12 C 0.5928(4) 0.6112(3) 0.48957(18) 0.0270 1.0000 Uani . . . . . . N13 N 0.5815(3) 0.6208(3) 0.42848(15) 0.0293 1.0000 Uani . . . . . . C14 C 0.4841(4) 0.6747(3) 0.4070(2) 0.0368 1.0000 Uani . . . . . . C15 C 0.3936(4) 0.7227(3) 0.4434(2) 0.0397 1.0000 Uani . . . . . . C16 C 0.4067(4) 0.7170(3) 0.5043(2) 0.0406 1.0000 Uani . . . . . . C17 C 0.5081(4) 0.6600(3) 0.52992(19) 0.0320 1.0000 Uani . . . . . . C18 C 0.5291(5) 0.6516(4) 0.5937(2) 0.0415 1.0000 Uani . . . . . . C19 C 0.6269(4) 0.5971(4) 0.61598(19) 0.0408 1.0000 Uani . . . . . . C20 C 0.7116(4) 0.5432(3) 0.57688(17) 0.0318 1.0000 Uani . . . . . . C21 C 0.8127(4) 0.4832(3) 0.5985(2) 0.0404 1.0000 Uani . . . . . . C22 C 0.8879(4) 0.4308(3) 0.5592(2) 0.0402 1.0000 Uani . . . . . . C23 C 0.8618(4) 0.4371(3) 0.49742(19) 0.0331 1.0000 Uani . . . . . . H31 H 0.9735 0.6980 0.2864 0.0337 1.0000 Uiso R . . . . . H41 H 1.0990 0.5831 0.2343 0.0369 1.0000 Uiso R . . . . . H51 H 1.0619 0.4027 0.2369 0.0359 1.0000 Uiso R . . . . . H141 H 0.4735 0.6790 0.3647 0.0430 1.0000 Uiso R . . . . . H151 H 0.3235 0.7583 0.4252 0.0470 1.0000 Uiso R . . . . . H161 H 0.3486 0.7509 0.5283 0.0482 1.0000 Uiso R . . . . . H181 H 0.4772 0.6863 0.6203 0.0489 1.0000 Uiso R . . . . . H191 H 0.6421 0.5939 0.6576 0.0481 1.0000 Uiso R . . . . . H211 H 0.8267 0.4797 0.6400 0.0469 1.0000 Uiso R . . . . . H221 H 0.9532 0.3903 0.5736 0.0478 1.0000 Uiso R . . . . . H231 H 0.9137 0.3994 0.4714 0.0383 1.0000 Uiso R . . . . . H91 H 0.8217 0.2869 0.3083 0.0568 1.0000 Uiso R . . . . . H11 H 0.7219 0.6295 0.3691 0.0474 1.0000 Uiso R . . . . . H81 H 0.7340 0.4598 0.3920 0.0446 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 0.0349(16) 0.0236(14) 0.0385(15) -0.0034(13) 0.0074(13) 0.0016(13) C2 0.0264(19) 0.027(2) 0.0225(19) -0.0003(16) -0.0027(17) 0.0024(17) C3 0.031(2) 0.028(2) 0.027(2) 0.0041(18) 0.0000(18) -0.0065(19) C4 0.032(2) 0.038(2) 0.024(2) 0.0032(19) 0.0060(18) -0.003(2) C5 0.029(2) 0.037(2) 0.026(2) -0.0027(19) 0.0033(17) 0.0049(19) C6 0.030(2) 0.026(2) 0.0230(19) -0.0029(17) 0.0006(17) 0.0001(19) C7 0.0241(19) 0.028(2) 0.0202(18) 0.0016(16) 0.0002(16) 0.0002(17) O8 0.0309(15) 0.0291(15) 0.0291(13) -0.0067(12) 0.0078(13) -0.0050(13) O9 0.0435(18) 0.0267(15) 0.0474(18) -0.0062(14) 0.0144(14) -0.0019(14) N10 0.0244(17) 0.0253(17) 0.0318(17) -0.0015(14) 0.0034(15) -0.0012(14) C11 0.0257(19) 0.0234(19) 0.0271(19) -0.0013(16) 0.0040(17) -0.0057(16) C12 0.027(2) 0.0206(19) 0.033(2) -0.0048(17) 0.0045(18) -0.0065(17) N13 0.0279(17) 0.0274(18) 0.0327(17) -0.0007(15) 0.0029(15) 0.0017(15) C14 0.033(2) 0.034(2) 0.043(2) -0.001(2) -0.002(2) 0.002(2) C15 0.030(2) 0.025(2) 0.064(3) 0.003(2) 0.000(2) 0.0029(19) C16 0.028(2) 0.027(2) 0.067(3) -0.011(2) 0.015(2) -0.0013(19) C17 0.030(2) 0.023(2) 0.043(2) -0.0084(19) 0.012(2) -0.0077(18) C18 0.048(3) 0.038(3) 0.039(2) -0.011(2) 0.023(2) -0.012(2) C19 0.055(3) 0.039(3) 0.028(2) -0.004(2) 0.009(2) -0.012(2) C20 0.037(2) 0.031(2) 0.0278(19) -0.0004(17) 0.0026(19) -0.0121(19) C21 0.050(3) 0.039(3) 0.032(2) 0.003(2) -0.008(2) -0.010(2) C22 0.039(2) 0.033(2) 0.049(3) 0.007(2) -0.013(2) -0.003(2) C23 0.028(2) 0.031(2) 0.041(2) 0.0011(19) 0.0013(19) 0.0006(19) _refine_ls_extinction_coef 210(20) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.2407(4) 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 . C2 . 1.377(4) yes O1 . H11 . 0.836 no C2 . C3 . 1.388(5) yes C2 . C7 . 1.388(5) yes C3 . C4 . 1.378(5) yes C3 . H31 . 0.933 no C4 . C5 . 1.382(5) yes C4 . H41 . 0.924 no C5 . C6 . 1.380(5) yes C5 . H51 . 0.926 no C6 . C7 . 1.393(5) yes C6 . O9 . 1.366(5) yes C7 . O8 . 1.380(4) yes O8 . H81 . 0.849 no O9 . H91 . 0.815 no N10 . C11 . 1.361(5) yes N10 . C23 . 1.324(5) yes C11 . C12 . 1.439(5) yes C11 . C20 . 1.413(5) yes C12 . N13 . 1.362(5) yes C12 . C17 . 1.412(5) yes N13 . C14 . 1.329(5) yes C14 . C15 . 1.395(6) yes C14 . H141 . 0.942 no C15 . C16 . 1.358(6) yes C15 . H151 . 0.959 no C16 . C17 . 1.416(6) yes C16 . H161 . 0.920 no C17 . C18 . 1.432(6) yes C18 . C19 . 1.343(6) yes C18 . H181 . 0.920 no C19 . C20 . 1.423(6) yes C19 . H191 . 0.936 no C20 . C21 . 1.401(6) yes C21 . C22 . 1.356(6) yes C21 . H211 . 0.932 no C22 . C23 . 1.397(6) yes C22 . H221 . 0.920 no C23 . H231 . 0.929 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 . O1 . H11 . 111.8 no O1 . C2 . C3 . 118.3(3) yes O1 . C2 . C7 . 121.9(3) yes C3 . C2 . C7 . 119.8(4) yes C2 . C3 . C4 . 119.8(4) yes C2 . C3 . H31 . 120.8 no C4 . C3 . H31 . 119.4 no C3 . C4 . C5 . 121.1(4) yes C3 . C4 . H41 . 119.1 no C5 . C4 . H41 . 119.8 no C4 . C5 . C6 . 119.0(4) yes C4 . C5 . H51 . 121.1 no C6 . C5 . H51 . 120.0 no C5 . C6 . C7 . 120.8(4) yes C5 . C6 . O9 . 119.4(3) yes C7 . C6 . O9 . 119.7(3) yes C6 . C7 . C2 . 119.4(3) yes C6 . C7 . O8 . 117.5(3) yes C2 . C7 . O8 . 122.9(3) yes C7 . O8 . H81 . 110.3 no C6 . O9 . H91 . 116.3 no C11 . N10 . C23 . 118.2(3) yes N10 . C11 . C12 . 118.9(3) yes N10 . C11 . C20 . 121.7(4) yes C12 . C11 . C20 . 119.4(3) yes C11 . C12 . N13 . 118.8(3) yes C11 . C12 . C17 . 119.1(4) yes N13 . C12 . C17 . 122.1(4) yes C12 . N13 . C14 . 118.0(3) yes N13 . C14 . C15 . 123.8(4) yes N13 . C14 . H141 . 118.6 no C15 . C14 . H141 . 117.6 no C14 . C15 . C16 . 118.6(4) yes C14 . C15 . H151 . 120.0 no C16 . C15 . H151 . 121.3 no C15 . C16 . C17 . 120.1(4) yes C15 . C16 . H161 . 118.5 no C17 . C16 . H161 . 121.4 no C16 . C17 . C12 . 117.2(4) yes C16 . C17 . C18 . 123.4(4) yes C12 . C17 . C18 . 119.4(4) yes C17 . C18 . C19 . 121.4(4) yes C17 . C18 . H181 . 120.1 no C19 . C18 . H181 . 118.4 no C18 . C19 . C20 . 120.9(4) yes C18 . C19 . H191 . 121.2 no C20 . C19 . H191 . 117.9 no C19 . C20 . C11 . 119.6(4) yes C19 . C20 . C21 . 122.6(4) yes C11 . C20 . C21 . 117.7(4) yes C20 . C21 . C22 . 120.0(4) yes C20 . C21 . H211 . 119.0 no C22 . C21 . H211 . 121.0 no C21 . C22 . C23 . 118.8(4) yes C21 . C22 . H221 . 119.8 no C23 . C22 . H221 . 121.3 no C22 . C23 . N10 . 123.5(4) yes C22 . C23 . H231 . 117.2 no N10 . C23 . H231 . 119.3 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 O9 . H91 . O1 3_645 147.84(10) 0.815 2.236 2.959(6) yes O1 . H11 . N13 . 153.02(12) 0.836 1.991 2.763(6) yes O8 . H81 . N10 . 165.15(12) 0.849 1.916 2.745(6) yes _iucr_refine_instruction_details_constraints ; # # Punched on 09/05/12 at 10:18:54 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE O ( 1,X'S) H ( 11,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE O ( 8,X'S) H ( 81,X'S) RIDE O ( 9,X'S) H ( 91,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 09/05/12 at 10:18:54 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 8 0 22 x .