# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Alan F. Williams' _publ_contact_author_address ;Department of Inorganic Chemistry University of Geneva 30 quai Ernest Ansermet CH 1211 Geneva 4 Switzerland ; _publ_contact_author_email Alan.Williams@unige.ch _publ_contact_author_phone '++41 22 3796425' loop_ _publ_author_name _publ_author_address 'Alan F. Williams' ;Department of Inorganic Chemistry University of Geneva 30 quai Ernest Ansermet CH 1211 Geneva 4 Switzerland ; S.E.Clifford ;Department of Inorganic Chemistry University of Geneva 30 quai Ernest Ansermet CH 1211 Geneva 4 Switzerland ; M.Runowski ;Department of Inorganic Chemistry University of Geneva 30 quai Ernest Ansermet CH 1211 Geneva 4 Switzerland ; N.Parthasarathy ;Department of Inorganic Chemistry University of Geneva 30 quai Ernest Ansermet CH 1211 Geneva 4 Switzerland ; ; C.Besnard ; ;Laboratory for X-ray Crystallography University of Geneva 24 quai Ernest Ansermet CH 1211 Geneva 4 Switzerland ; X.Melich ;Department of Inorganic Chemistry University of Geneva 30 quai Ernest Ansermet CH 1211 Geneva 4 Switzerland ; A.F.Williams ;Department of Inorganic Chemistry University of Geneva 30 quai Ernest Ansermet CH 1211 Geneva 4 Switzerland ; _publ_section_title ; Phosphate binding to benzimidazole cations in the presence of water ; data_4(H2PO4)2 _database_code_depnum_ccdc_archive 'CCDC 848424' #TrackingRef '- bzimphos.cif' _cell_length_a 9.6451(11) _cell_length_b 9.7718(11) _cell_length_c 13.5760(13) _cell_angle_alpha 99.752(8) _cell_angle_beta 98.148(8) _cell_angle_gamma 115.368(8) _cell_volume 1106.0(2) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 # 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 . _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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' _cell_formula_units_Z 2 _chemical_name_systematic '1,5-bis(benzimidazolonium)pentane bis(dihydrogenophosphate)' _chemical_formula_moiety 'C19 H22 N4, 2(H2 O4 P)' # Given Formula = C19 H27 N4 O8 P2 # Dc = 1.51 Fooo = 524.00 Mu = 2.52 M = 501.39 # Found Formula = C19 H26 N4 O8 P2 # Dc = 1.50 FOOO = 524.00 Mu = 2.52 M = 500.39 _chemical_formula_sum 'C19 H26 N4 O8 P2' _chemical_compound_source ? _chemical_formula_weight 500.39 _cell_measurement_temperature 230 _cell_measurement_reflns_used 19568 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 31.59 _exptl_crystal_description prism _exptl_crystal_colour white _diffrn_ambient_temperature 230 _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.252 # Sheldrick geometric approximatio 0.96 0.97 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details ; Gaussian Integration (Busing and Levy, 1957) ; _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device 'Stoe IPDS' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'IPDS (Stoe & Cie, 1996)' _computing_cell_refinement 'IPDS (Stoe & Cie, 1996)' _computing_data_reduction 'XRED (Stoe & Cie 1996)' _computing_structure_solution 'Sir2004 (Burla et al., 2005)' _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_reflns_number 21657 _reflns_number_total 7093 _diffrn_reflns_av_R_equivalents 0.047 # Number of reflections with Friedels Law is 7093 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7240 _diffrn_reflns_theta_min 2.387 _diffrn_reflns_theta_max 31.305 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 30.053 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -14 _reflns_limit_h_max 13 _reflns_limit_k_min -14 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.40 _refine_diff_density_max 0.52 # 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>-10.0\s(I) _refine_ls_number_reflns 7078 _refine_ls_number_restraints 0 _refine_ls_number_parameters 402 _oxford_refine_ls_R_factor_ref 0.0550 _refine_ls_wR_factor_ref 0.0613 _refine_ls_goodness_of_fit_ref 1.0613 _refine_ls_shift/su_max 0.000486 # The values computed from all data _oxford_reflns_number_all 7078 _refine_ls_R_factor_all 0.0550 _refine_ls_wR_factor_all 0.0613 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5522 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_gt 0.0573 _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refall # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.63 1.62 0.357 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Burla, M. C. , Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., D Caro, L. , Giacovazzo, C., Polidori, G., & Spagna R. J. Appl. Cryst. (2005). 381-388. Busing, W.R. & Levy, H.A., (1975). Acta Cryst 10, 180. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Stoe & Cie (1996). IPDS Software. Stoe & Cie (1996). XRED V1.08. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens P1 P 0.51256(4) 0.02631(4) 0.65164(3) 0.0247 1.0000 Uani . . . . . . . O2 O 0.66903(12) 0.07549(14) 0.61303(9) 0.0336 1.0000 Uani . . . . . . . H21 H 0.657(2) 0.085(3) 0.5515(17) 0.065(7) 1.0000 Uiso . . . . . . . O4 O 0.47296(13) 0.16739(14) 0.66004(9) 0.0338 1.0000 Uani . . . . . . . H41 H 0.542(2) 0.240(2) 0.6965(17) 0.057(7) 1.0000 Uiso . . . . . . . O6 O 0.54824(12) 0.00136(12) 0.75700(7) 0.0290 1.0000 Uani . . . . . . . O7 O 0.37605(12) -0.11125(12) 0.57418(8) 0.0343 1.0000 Uani . . . . . . . P8 P 0.78367(4) 0.39197(4) 0.88748(3) 0.0254 1.0000 Uani . . . . . . . O9 O 0.83448(12) 0.52864(12) 0.97879(8) 0.0301 1.0000 Uani . . . . . . . O10 O 0.71578(12) 0.41039(12) 0.78696(8) 0.0315 1.0000 Uani . . . . . . . O11 O 0.66007(15) 0.24486(14) 0.91461(9) 0.0377 1.0000 Uani . . . . . . . H111 H 0.620(2) 0.170(2) 0.8688(15) 0.050(6) 1.0000 Uiso . . . . . . . O13 O 0.92581(14) 0.36030(16) 0.87066(10) 0.0451 1.0000 Uani . . . . . . . H131 H 1.003(3) 0.395(3) 0.9222(17) 0.068(7) 1.0000 Uiso . . . . . . . N15 N 0.17346(14) 0.22513(15) 0.07815(10) 0.0287 1.0000 Uani . . . . . . . C16 C 0.04683(16) 0.14184(16) 0.11770(11) 0.0275 1.0000 Uani . . . . . . . C17 C 0.09120(17) 0.05258(17) 0.17164(11) 0.0302 1.0000 Uani . . . . . . . N18 N 0.24357(16) 0.08642(16) 0.16293(10) 0.0320 1.0000 Uani . . . . . . . C19 C 0.28931(17) 0.18980(17) 0.10684(11) 0.0285 1.0000 Uani . . . . . . . C20 C 0.44499(19) 0.2544(2) 0.07924(13) 0.0357 1.0000 Uani . . . . . . . C21 C 0.54336(18) 0.4322(2) 0.12218(12) 0.0332 1.0000 Uani . . . . . . . C22 C 0.58507(19) 0.48708(19) 0.23859(12) 0.0321 1.0000 Uani . . . . . . . C23 C 0.67721(17) 0.41894(18) 0.29628(11) 0.0291 1.0000 Uani . . . . . . . C24 C 0.83775(18) 0.4638(2) 0.27143(13) 0.0320 1.0000 Uani . . . . . . . C25 C 0.93854(16) 0.41346(16) 0.33308(11) 0.0263 1.0000 Uani . . . . . . . N26 N 0.89401(14) 0.31855(14) 0.39503(9) 0.0275 1.0000 Uani . . . . . . . C27 C 1.01951(16) 0.29361(16) 0.43475(11) 0.0270 1.0000 Uani . . . . . . . C28 C 1.14439(16) 0.38000(17) 0.39444(10) 0.0278 1.0000 Uani . . . . . . . N29 N 1.08984(14) 0.45458(15) 0.33283(10) 0.0294 1.0000 Uani . . . . . . . H291 H 1.140(2) 0.509(2) 0.2936(16) 0.056(6) 1.0000 Uiso . . . . . . . C31 C 1.28858(19) 0.3779(2) 0.41646(12) 0.0361 1.0000 Uani . . . . . . . C32 C 1.3008(2) 0.2846(2) 0.47920(13) 0.0393 1.0000 Uani . . . . . . . C33 C 1.1761(2) 0.19997(19) 0.52089(13) 0.0385 1.0000 Uani . . . . . . . C34 C 1.03335(19) 0.20283(18) 0.50032(12) 0.0335 1.0000 Uani . . . . . . . H341 H 0.948(2) 0.150(2) 0.5289(13) 0.038(5) 1.0000 Uiso . . . . . . . H331 H 1.194(2) 0.139(2) 0.5674(13) 0.039(5) 1.0000 Uiso . . . . . . . H321 H 1.396(2) 0.277(2) 0.4948(14) 0.047(5) 1.0000 Uiso . . . . . . . H311 H 1.369(2) 0.437(2) 0.3876(14) 0.044(5) 1.0000 Uiso . . . . . . . H261 H 0.801(2) 0.267(2) 0.3998(14) 0.048(6) 1.0000 Uiso . . . . . . . H241 H 0.894(2) 0.576(2) 0.2781(15) 0.056(6) 1.0000 Uiso . . . . . . . H242 H 0.829(2) 0.421(2) 0.1968(14) 0.041(5) 1.0000 Uiso . . . . . . . H231 H 0.6904(19) 0.4557(19) 0.3699(13) 0.032(4) 1.0000 Uiso . . . . . . . H232 H 0.6165(19) 0.305(2) 0.2801(12) 0.034(4) 1.0000 Uiso . . . . . . . H222 H 0.648(2) 0.602(2) 0.2608(13) 0.041(5) 1.0000 Uiso . . . . . . . H221 H 0.486(2) 0.4613(19) 0.2609(12) 0.034(4) 1.0000 Uiso . . . . . . . H211 H 0.642(2) 0.466(2) 0.0981(14) 0.045(5) 1.0000 Uiso . . . . . . . H212 H 0.485(2) 0.486(2) 0.0949(13) 0.037(5) 1.0000 Uiso . . . . . . . H201 H 0.501(2) 0.200(2) 0.1046(14) 0.042(5) 1.0000 Uiso . . . . . . . H202 H 0.425(2) 0.230(2) 0.0017(14) 0.038(5) 1.0000 Uiso . . . . . . . H181 H 0.303(2) 0.054(2) 0.1915(15) 0.048(6) 1.0000 Uiso . . . . . . . C51 C -0.0090(2) -0.0452(2) 0.22179(14) 0.0425 1.0000 Uani . . . . . . . C52 C -0.1544(2) -0.0479(2) 0.21570(15) 0.0467 1.0000 Uani . . . . . . . C53 C -0.1991(2) 0.0414(2) 0.16120(14) 0.0417 1.0000 Uani . . . . . . . C54 C -0.10001(18) 0.13805(19) 0.11046(13) 0.0348 1.0000 Uani . . . . . . . H541 H -0.1313(19) 0.196(2) 0.0700(13) 0.036(5) 1.0000 Uiso . . . . . . . H531 H -0.302(2) 0.036(2) 0.1597(15) 0.052(6) 1.0000 Uiso . . . . . . . H521 H -0.223(2) -0.110(2) 0.2516(16) 0.065(6) 1.0000 Uiso . . . . . . . H511 H 0.024(2) -0.103(2) 0.2596(15) 0.053(6) 1.0000 Uiso . . . . . . . H151 H 0.179(2) 0.302(2) 0.0507(15) 0.050(6) 1.0000 Uiso . . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01998(15) 0.02790(18) 0.02633(17) 0.01179(14) 0.00639(13) 0.00916(13) O2 0.0232(5) 0.0449(6) 0.0332(6) 0.0151(5) 0.0100(4) 0.0134(5) O4 0.0286(5) 0.0361(6) 0.0383(6) 0.0132(5) 0.0018(5) 0.0171(5) O6 0.0314(5) 0.0314(5) 0.0282(5) 0.0138(4) 0.0083(4) 0.0156(4) O7 0.0272(5) 0.0343(6) 0.0296(5) 0.0112(4) 0.0069(4) 0.0025(4) P8 0.02587(17) 0.02987(18) 0.02467(17) 0.01069(14) 0.00850(13) 0.01457(14) O9 0.0308(5) 0.0322(5) 0.0301(5) 0.0081(4) 0.0069(4) 0.0173(4) O10 0.0315(5) 0.0325(5) 0.0300(5) 0.0150(4) 0.0066(4) 0.0123(4) O11 0.0504(7) 0.0302(6) 0.0311(6) 0.0129(5) 0.0179(5) 0.0131(5) O13 0.0350(6) 0.0665(9) 0.0348(6) -0.0034(6) 0.0031(5) 0.0320(6) N15 0.0268(6) 0.0281(6) 0.0336(6) 0.0109(5) 0.0079(5) 0.0135(5) C16 0.0255(6) 0.0247(7) 0.0306(7) 0.0054(5) 0.0068(5) 0.0109(5) C17 0.0318(7) 0.0298(7) 0.0306(7) 0.0069(6) 0.0083(6) 0.0158(6) N18 0.0338(7) 0.0373(7) 0.0325(6) 0.0117(5) 0.0073(5) 0.0225(6) C19 0.0269(7) 0.0317(7) 0.0271(7) 0.0046(5) 0.0051(5) 0.0153(6) C20 0.0292(7) 0.0468(9) 0.0324(8) 0.0058(7) 0.0096(6) 0.0195(7) C21 0.0272(7) 0.0440(9) 0.0330(8) 0.0180(7) 0.0111(6) 0.0166(7) C22 0.0309(7) 0.0356(8) 0.0341(8) 0.0112(6) 0.0106(6) 0.0175(7) C23 0.0285(7) 0.0331(8) 0.0265(7) 0.0108(6) 0.0094(5) 0.0132(6) C24 0.0287(7) 0.0379(8) 0.0350(8) 0.0185(7) 0.0115(6) 0.0160(6) C25 0.0240(6) 0.0267(7) 0.0258(6) 0.0075(5) 0.0076(5) 0.0089(5) N26 0.0221(6) 0.0286(6) 0.0295(6) 0.0111(5) 0.0083(5) 0.0079(5) C27 0.0242(6) 0.0260(7) 0.0265(7) 0.0061(5) 0.0048(5) 0.0085(5) C28 0.0256(6) 0.0308(7) 0.0247(6) 0.0072(5) 0.0067(5) 0.0109(6) N29 0.0244(6) 0.0348(7) 0.0291(6) 0.0142(5) 0.0101(5) 0.0104(5) C31 0.0274(7) 0.0478(9) 0.0327(8) 0.0101(7) 0.0093(6) 0.0166(7) C32 0.0337(8) 0.0449(9) 0.0387(9) 0.0056(7) 0.0013(7) 0.0217(7) C33 0.0413(9) 0.0303(8) 0.0384(8) 0.0087(7) -0.0015(7) 0.0153(7) C34 0.0329(8) 0.0280(7) 0.0336(8) 0.0106(6) 0.0051(6) 0.0086(6) C51 0.0491(10) 0.0405(9) 0.0426(9) 0.0186(8) 0.0172(8) 0.0202(8) C52 0.0433(10) 0.0432(10) 0.0481(10) 0.0137(8) 0.0230(8) 0.0107(8) C53 0.0285(8) 0.0417(9) 0.0488(10) 0.0028(8) 0.0138(7) 0.0128(7) C54 0.0283(7) 0.0332(8) 0.0422(9) 0.0047(7) 0.0074(6) 0.0157(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.36862(18) 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 P1 . O2 . 1.5721(11) yes P1 . O4 . 1.5715(12) yes P1 . O6 . 1.5080(10) yes P1 . O7 . 1.5028(11) yes O2 . H21 . 0.85(2) no O4 . H41 . 0.76(2) no P8 . O9 . 1.5055(11) yes P8 . O10 . 1.5015(10) yes P8 . O11 . 1.5680(12) yes P8 . O13 . 1.5671(12) yes O11 . H111 . 0.78(2) no O13 . H131 . 0.85(2) no N15 . C16 . 1.3873(18) yes N15 . C19 . 1.3312(18) yes N15 . H151 . 0.874(19) no C16 . C17 . 1.388(2) yes C16 . C54 . 1.390(2) yes C17 . N18 . 1.3890(19) yes C17 . C51 . 1.388(2) yes N18 . C19 . 1.3300(19) yes N18 . H181 . 0.846(19) no C19 . C20 . 1.490(2) yes C20 . C21 . 1.532(2) yes C20 . H201 . 0.973(18) no C20 . H202 . 1.010(17) no C21 . C22 . 1.515(2) yes C21 . H211 . 0.987(18) no C21 . H212 . 0.997(17) no C22 . C23 . 1.527(2) yes C22 . H222 . 0.984(18) no C22 . H221 . 0.981(16) no C23 . C24 . 1.523(2) yes C23 . H231 . 0.974(17) no C23 . H232 . 0.975(17) no C24 . C25 . 1.486(2) yes C24 . H241 . 0.97(2) no C24 . H242 . 1.006(18) no C25 . N26 . 1.3331(17) yes C25 . N29 . 1.3380(17) yes N26 . C27 . 1.3885(18) yes N26 . H261 . 0.836(18) no C27 . C28 . 1.3910(19) yes C27 . C34 . 1.390(2) yes C28 . N29 . 1.3849(19) yes C28 . C31 . 1.390(2) yes N29 . H291 . 0.86(2) no C31 . C32 . 1.378(2) yes C31 . H311 . 0.934(18) no C32 . C33 . 1.397(2) yes C32 . H321 . 0.946(18) no C33 . C34 . 1.378(2) yes C33 . H331 . 0.988(17) no C34 . H341 . 0.946(17) no C51 . C52 . 1.381(3) yes C51 . H511 . 0.945(19) no C52 . C53 . 1.395(3) yes C52 . H521 . 0.95(2) no C53 . C54 . 1.383(2) yes C53 . H531 . 0.969(19) no C54 . H541 . 0.958(17) 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 O2 . P1 . O4 . 107.09(6) yes O2 . P1 . O6 . 106.65(6) yes O4 . P1 . O6 . 109.86(6) yes O2 . P1 . O7 . 111.04(6) yes O4 . P1 . O7 . 106.65(7) yes O6 . P1 . O7 . 115.30(6) yes P1 . O2 . H21 . 112.7(14) no P1 . O4 . H41 . 109.1(16) no O9 . P8 . O10 . 114.98(6) yes O9 . P8 . O11 . 106.27(6) yes O10 . P8 . O11 . 110.70(6) yes O9 . P8 . O13 . 111.18(6) yes O10 . P8 . O13 . 106.16(7) yes O11 . P8 . O13 . 107.37(7) yes P8 . O11 . H111 . 113.3(15) no P8 . O13 . H131 . 116.6(15) no C16 . N15 . C19 . 108.90(12) yes C16 . N15 . H151 . 122.7(12) no C19 . N15 . H151 . 127.2(12) no N15 . C16 . C17 . 106.52(12) yes N15 . C16 . C54 . 131.38(14) yes C17 . C16 . C54 . 122.10(14) yes C16 . C17 . N18 . 106.22(13) yes C16 . C17 . C51 . 121.63(15) yes N18 . C17 . C51 . 132.15(15) yes C17 . N18 . C19 . 109.04(12) yes C17 . N18 . H181 . 127.3(13) no C19 . N18 . H181 . 123.5(13) no N15 . C19 . N18 . 109.32(13) yes N15 . C19 . C20 . 125.33(14) yes N18 . C19 . C20 . 125.35(14) yes C19 . C20 . C21 . 113.28(13) yes C19 . C20 . H201 . 107.2(10) no C21 . C20 . H201 . 111.0(11) no C19 . C20 . H202 . 108.2(10) no C21 . C20 . H202 . 108.0(10) no H201 . C20 . H202 . 109.1(14) no C20 . C21 . C22 . 114.24(13) yes C20 . C21 . H211 . 108.2(10) no C22 . C21 . H211 . 108.9(10) no C20 . C21 . H212 . 110.2(10) no C22 . C21 . H212 . 107.4(10) no H211 . C21 . H212 . 107.7(14) no C21 . C22 . C23 . 115.95(13) yes C21 . C22 . H222 . 109.9(10) no C23 . C22 . H222 . 107.1(10) no C21 . C22 . H221 . 108.0(10) no C23 . C22 . H221 . 108.8(10) no H222 . C22 . H221 . 106.8(14) no C22 . C23 . C24 . 111.93(12) yes C22 . C23 . H231 . 108.9(10) no C24 . C23 . H231 . 110.2(10) no C22 . C23 . H232 . 110.4(10) no C24 . C23 . H232 . 109.7(10) no H231 . C23 . H232 . 105.5(13) no C23 . C24 . C25 . 114.08(12) yes C23 . C24 . H241 . 110.9(12) no C25 . C24 . H241 . 110.2(12) no C23 . C24 . H242 . 112.6(10) no C25 . C24 . H242 . 107.2(10) no H241 . C24 . H242 . 101.2(15) no C24 . C25 . N26 . 126.40(12) yes C24 . C25 . N29 . 124.59(12) yes N26 . C25 . N29 . 108.99(12) yes C25 . N26 . C27 . 109.04(11) yes C25 . N26 . H261 . 125.9(13) no C27 . N26 . H261 . 123.9(13) no N26 . C27 . C28 . 106.45(12) yes N26 . C27 . C34 . 131.81(13) yes C28 . C27 . C34 . 121.73(14) yes C27 . C28 . N29 . 106.36(12) yes C27 . C28 . C31 . 121.62(14) yes N29 . C28 . C31 . 132.00(14) yes C28 . N29 . C25 . 109.12(12) yes C28 . N29 . H291 . 126.4(13) no C25 . N29 . H291 . 124.0(13) no C28 . C31 . C32 . 116.62(15) yes C28 . C31 . H311 . 119.0(11) no C32 . C31 . H311 . 124.4(11) no C31 . C32 . C33 . 121.60(15) yes C31 . C32 . H321 . 119.7(11) no C33 . C32 . H321 . 118.7(11) no C32 . C33 . C34 . 122.09(15) yes C32 . C33 . H331 . 117.3(10) no C34 . C33 . H331 . 120.6(10) no C27 . C34 . C33 . 116.30(15) yes C27 . C34 . H341 . 119.1(10) no C33 . C34 . H341 . 124.5(10) no C17 . C51 . C52 . 116.41(16) yes C17 . C51 . H511 . 120.7(12) no C52 . C51 . H511 . 122.9(12) no C51 . C52 . C53 . 121.92(16) yes C51 . C52 . H521 . 118.2(13) no C53 . C52 . H521 . 119.9(13) no C52 . C53 . C54 . 121.83(16) yes C52 . C53 . H531 . 118.6(11) no C54 . C53 . H531 . 119.6(11) no C16 . C54 . C53 . 116.11(16) yes C16 . C54 . H541 . 121.2(10) no C53 . C54 . H541 . 122.6(10) no _chemical_name_common '1,5-bis(benzimidazolonium)pentane bis(dihydrogenophosphate)' #==END data_2(SO4)3H2O _database_code_depnum_ccdc_archive 'CCDC 848425' #TrackingRef '- bzimphos.cif' _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; The H atoms were located using difference map and possible hydrogen bonds. Their positions was idealized and they were then refined with riding constraints. CHCEKCIF indicates a possible center of symmetry and proposes the space group P21/c. Refining the structure in this space group implies using a disordered model to take into account the differences in the two molecules in the middle of the chain. Such a refinement was not satisfactory so that the non-centrosymmetrix space group was used. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; _cell_length_a 6.9865(8) _cell_length_b 17.3680(10) _cell_length_c 15.8470(10) _cell_angle_alpha 90 _cell_angle_beta 94.68(3) _cell_angle_gamma 90 _cell_volume 1916.5(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 n 1 ' _symmetry_space_group_name_Hall 'P -2yac ' loop_ _symmetry_equiv_pos_as_xyz x,y,z 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' 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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 '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' 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' _cell_formula_units_Z 2 _chemical_name_systematic '1,2-bis(benzimidazolonium)ethane sulphate trihydrate' # Given Formula = C34 H9 Cl4 N8 O4 S2 # Dc = 1.39 Fooo = 904.00 Mu = 4.65 M = 799.44 # Found Formula = C34 H48 N8 O14 S2 # Dc = 1.48 FOOO = 904.00 Mu = 2.19 M = 856.93 _chemical_formula_sum 'C34 H48 N8 O14 S2' _chemical_formula_moiety '2(C17 H18 N4), 0.5(H4 O2), 2(O4 S), 5(H2 O)' _chemical_compound_source ? _chemical_formula_weight 856.93 _cell_measurement_reflns_used 17102 _cell_measurement_theta_min 2.345 _cell_measurement_theta_max 28.301 _cell_measurement_temperature 220 _exptl_crystal_description 'elongated platelet' _exptl_crystal_colour yellow _exptl_crystal_size_min 0.01 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.219 # Sheldrick geometric approximatio 0.98 1.00 _exptl_absorpt_correction_type none _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_voltage 55 _diffrn_source_current 35 _diffrn_source_power 1.93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_collimation '0.5 mm diameter, monocapillary' _diffrn_measurement_method 'rotation method' _diffrn_measurement_details ; 145 frames, detector distance = 70 mm ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'STOE XAREA' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'Sir2004 (Burla et al., 2005)' _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 200 _diffrn_reflns_number 17102 _reflns_number_total 8995 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections with Friedels Law is 4753 # Number of reflections without Friedels Law is 8995 # Theoretical number of reflections is about 3760 _diffrn_reflns_theta_min 2.345 _diffrn_reflns_theta_max 28.301 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.301 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 23 _reflns_limit_l_min -21 _reflns_limit_l_max 21 _oxford_diffrn_Wilson_B_factor 1.35 _oxford_diffrn_Wilson_scale 0.10 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.52 _refine_diff_density_max 0.32 # 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>-10.0\s(I) _refine_ls_number_reflns 7119 _refine_ls_number_restraints 2 _refine_ls_number_parameters 533 _oxford_refine_ls_R_factor_ref 0.0388 _refine_ls_wR_factor_ref 0.0536 _refine_ls_goodness_of_fit_ref 1.7020 _refine_ls_shift/su_max 0.000677 # The values computed from all data _oxford_reflns_number_all 7119 _refine_ls_R_factor_all 0.0388 _refine_ls_wR_factor_all 0.0536 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6656 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_gt 0.0530 _refine_ls_abs_structure_Flack 0.08(5) _refine_ls_abs_structure_details 'Flack (1983), 4242 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 343. 447. 230. 93.4 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Burla, M. C. , Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., D Caro, L. , Giacovazzo, C., Polidori, G., & Spagna R. J. Appl. Cryst. (2005). 381-388. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Kabsch, W. (1993).J. Appl. Cryst. 26, 795-800 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C -0.2444(4) 0.03925(15) 1.40968(16) 0.0249 1.0000 Uani . . . . . . . C2 C -0.1982(4) -0.03502(15) 1.43983(15) 0.0256 1.0000 Uani . . . . . . . C3 C -0.1811(3) -0.09618(15) 1.38580(15) 0.0233 1.0000 Uani . . . . . . . C4 C -0.2138(3) -0.08105(13) 1.29909(14) 0.0182 1.0000 Uani . . . . . . . C5 C -0.2582(3) -0.00728(13) 1.26964(15) 0.0174 1.0000 Uani . . . . . . . C6 C -0.2759(3) 0.05500(14) 1.32437(15) 0.0210 1.0000 Uani . . . . . . . N7 N -0.2077(3) -0.12726(11) 1.22768(12) 0.0180 1.0000 Uani . . . . . . . N8 N -0.2781(3) -0.01152(11) 1.18252(12) 0.0178 1.0000 Uani . . . . . . . C9 C -0.2475(3) -0.08411(13) 1.15971(14) 0.0178 1.0000 Uani . . . . . . . C10 C -0.2552(4) -0.11354(12) 1.07104(14) 0.0206 1.0000 Uani . . . . . . . C11 C -0.2313(3) -0.04849(13) 1.00815(13) 0.0199 1.0000 Uani . . . . . . . C12 C -0.2433(3) -0.07681(12) 0.91682(13) 0.0187 1.0000 Uani . . . . . . . C13 C -0.2354(3) -0.01108(13) 0.85718(15) 0.0174 1.0000 Uani . . . . . . . N14 N -0.2045(3) 0.06193(11) 0.87984(12) 0.0170 1.0000 Uani . . . . . . . N15 N -0.2605(3) -0.01559(12) 0.77310(12) 0.0204 1.0000 Uani . . . . . . . C16 C -0.2433(3) 0.05816(14) 0.73935(15) 0.0186 1.0000 Uani . . . . . . . C17 C -0.2086(3) 0.10713(14) 0.80731(15) 0.0195 1.0000 Uani . . . . . . . C18 C -0.1867(4) 0.18678(14) 0.79771(16) 0.0250 1.0000 Uani . . . . . . . C19 C -0.1995(4) 0.21335(16) 0.71563(17) 0.0317 1.0000 Uani . . . . . . . C20 C -0.2329(4) 0.16300(16) 0.64627(15) 0.0304 1.0000 Uani . . . . . . . C21 C -0.2567(4) 0.08525(16) 0.65606(15) 0.0264 1.0000 Uani . . . . . . . C22 C 0.6349(4) 0.70440(15) 0.46297(16) 0.0282 1.0000 Uani . . . . . . . C23 C 0.6349(3) 0.65911(16) 0.53635(15) 0.0294 1.0000 Uani . . . . . . . C24 C 0.6659(3) 0.58092(15) 0.53522(14) 0.0242 1.0000 Uani . . . . . . . C25 C 0.6966(3) 0.54881(14) 0.45665(15) 0.0192 1.0000 Uani . . . . . . . C26 C 0.6958(3) 0.59393(14) 0.38387(14) 0.0184 1.0000 Uani . . . . . . . C27 C 0.6650(4) 0.67211(15) 0.38557(16) 0.0258 1.0000 Uani . . . . . . . N28 N 0.7294(3) 0.54241(11) 0.31820(11) 0.0173 1.0000 Uani . . . . . . . N29 N 0.7309(3) 0.47407(12) 0.43256(12) 0.0184 1.0000 Uani . . . . . . . C30 C 0.7504(3) 0.47220(14) 0.34916(14) 0.0170 1.0000 Uani . . . . . . . C31 C 0.7880(3) 0.39931(13) 0.30290(14) 0.0202 1.0000 Uani . . . . . . . C32 C 0.8162(3) 0.40793(13) 0.20854(13) 0.0187 1.0000 Uani . . . . . . . C33 C 0.6266(3) 0.40776(13) 0.15280(13) 0.0190 1.0000 Uani . . . . . . . C34 C 0.6555(3) 0.42374(12) 0.06209(14) 0.0165 1.0000 Uani . . . . . . . N35 N 0.7000(3) 0.49323(11) 0.03465(11) 0.0174 1.0000 Uani . . . . . . . N36 N 0.6391(3) 0.37424(11) -0.00173(12) 0.0177 1.0000 Uani . . . . . . . C37 C 0.6769(3) 0.41335(14) -0.07537(14) 0.0169 1.0000 Uani . . . . . . . C38 C 0.7161(3) 0.48974(13) -0.05150(15) 0.0179 1.0000 Uani . . . . . . . C39 C 0.7570(4) 0.54538(15) -0.10996(16) 0.0255 1.0000 Uani . . . . . . . C40 C 0.7574(4) 0.52200(16) -0.19297(16) 0.0292 1.0000 Uani . . . . . . . C41 C 0.7160(4) 0.44629(17) -0.21730(15) 0.0294 1.0000 Uani . . . . . . . C42 C 0.6741(3) 0.39031(15) -0.15939(15) 0.0231 1.0000 Uani . . . . . . . S43 S 0.20573(9) 0.82516(3) 0.57097(4) 0.0170 1.0000 Uani . . . . . . . O44 O 0.0774(2) 0.88691(9) 0.59969(11) 0.0274 1.0000 Uani . . . . . . . O45 O 0.3689(2) 0.86287(9) 0.53355(10) 0.0242 1.0000 Uani . . . . . . . O46 O 0.0962(3) 0.77861(10) 0.50682(12) 0.0304 1.0000 Uani . . . . . . . O47 O 0.2754(3) 0.77777(10) 0.64365(11) 0.0321 1.0000 Uani . . . . . . . S48 S 0.78596(9) 0.67748(3) 0.13168(4) 0.0156 1.0000 Uani . . . . . . . O49 O 0.7662(3) 0.59535(9) 0.15727(10) 0.0282 1.0000 Uani . . . . . . . O50 O 0.6003(2) 0.70550(10) 0.09442(11) 0.0301 1.0000 Uani . . . . . . . O51 O 0.9273(3) 0.68224(11) 0.06853(11) 0.0375 1.0000 Uani . . . . . . . O52 O 0.8485(3) 0.72163(10) 0.20779(11) 0.0293 1.0000 Uani . . . . . . . O53 O 0.7776(3) 0.38685(10) 0.57105(11) 0.0270 1.0000 Uani . . . . . . . O54 O 1.1015(8) 0.2544(3) 0.2658(4) 0.0379 0.5000 Uani . . . . 2 . . O55 O 1.0868(8) 0.2098(3) 0.2730(4) 0.0542 0.5000 Uani . . . . 1 . . O56 O 0.4820(3) 0.24249(13) 0.26930(13) 0.0550 1.0000 Uani . . . . . . . O57 O 0.5850(3) 0.23117(12) 0.44019(12) 0.0416 1.0000 Uani . . . . . . . O58 O -0.0197(3) 0.24592(13) 0.43035(12) 0.0500 1.0000 Uani . . . . . . . O59 O 0.7006(3) 0.88793(14) 0.64031(12) 0.0451 1.0000 Uani . . . . . . . H562 H 0.3467 0.2323 0.2612 0.0500 1.0000 Uiso R . . . . . . H561 H 0.5289 0.2315 0.2154 0.0500 1.0000 Uiso R . . . . . . H532 H 0.6624 0.3612 0.5847 0.0500 1.0000 Uiso R . . . . . . H531 H 0.8796 0.3538 0.5934 0.0500 1.0000 Uiso R . . . . . . H592 H 0.5970 0.8742 0.5995 0.0500 1.0000 Uiso R . . . . . . H591 H 0.8141 0.8714 0.6154 0.0500 1.0000 Uiso R . . . . . . H582 H 0.0256 0.2627 0.4861 0.0500 1.0000 Uiso R . . . . . . H581 H -0.1561 0.2409 0.4323 0.0500 1.0000 Uiso R . . . . . . H571 H 0.5331 0.2422 0.3836 0.0500 1.0000 Uiso R . . . . . . H572 H 0.5169 0.2650 0.4750 0.0500 1.0000 Uiso R . . . . . . H551 H 0.9756 0.2128 0.2333 0.0500 0.5000 Uiso R . . . 1 . . H542 H 0.9906 0.2441 0.2276 0.0500 0.5000 Uiso R . . . 2 . . H552 H 1.0388 0.2206 0.3267 0.0500 0.5000 Uiso R . . . 1 . . H541 H 1.0550 0.2515 0.3209 0.0500 0.5000 Uiso R . . . 2 . . H141 H -0.1978 0.0900 0.9235 0.0500 1.0000 Uiso R . . . . . . H211 H -0.2801 0.0517 0.6089 0.0372 1.0000 Uiso R . . . . . . H201 H -0.2394 0.1845 0.5910 0.0437 1.0000 Uiso R . . . . . . H191 H -0.1854 0.2670 0.7061 0.0413 1.0000 Uiso R . . . . . . H181 H -0.1631 0.2202 0.8449 0.0343 1.0000 Uiso R . . . . . . H151 H -0.2941 -0.0571 0.7406 0.0500 1.0000 Uiso R . . . . . . H121 H -0.1372 -0.1099 0.9100 0.0275 1.0000 Uiso R . . . . . . H122 H -0.3599 -0.1044 0.9046 0.0275 1.0000 Uiso R . . . . . . H112 H -0.1099 -0.0247 1.0215 0.0276 1.0000 Uiso R . . . . . . H111 H -0.3307 -0.0119 1.0134 0.0276 1.0000 Uiso R . . . . . . H101 H -0.1550 -0.1500 1.0666 0.0302 1.0000 Uiso R . . . . . . H102 H -0.3761 -0.1378 1.0578 0.0302 1.0000 Uiso R . . . . . . H81 H -0.3148 0.0240 1.1504 0.0500 1.0000 Uiso R . . . . . . H31 H -0.1483 -0.1464 1.4061 0.0312 1.0000 Uiso R . . . . . . H21 H -0.1788 -0.0432 1.4992 0.0337 1.0000 Uiso R . . . . . . H11 H -0.2549 0.0797 1.4495 0.0336 1.0000 Uiso R . . . . . . H61 H -0.3064 0.1055 1.3043 0.0292 1.0000 Uiso R . . . . . . H71 H -0.1862 -0.1777 1.2244 0.0500 1.0000 Uiso R . . . . . . H351 H 0.7381 0.5335 0.0663 0.0500 1.0000 Uiso R . . . . . . H391 H 0.7809 0.5973 -0.0933 0.0323 1.0000 Uiso R . . . . . . H401 H 0.7874 0.5585 -0.2346 0.0379 1.0000 Uiso R . . . . . . H411 H 0.7164 0.4328 -0.2754 0.0388 1.0000 Uiso R . . . . . . H421 H 0.6456 0.3387 -0.1760 0.0309 1.0000 Uiso R . . . . . . H361 H 0.6827 0.3251 -0.0024 0.0500 1.0000 Uiso R . . . . . . H331 H 0.5446 0.4462 0.1727 0.0279 1.0000 Uiso R . . . . . . H332 H 0.5677 0.3587 0.1567 0.0279 1.0000 Uiso R . . . . . . H322 H 0.8807 0.4552 0.2003 0.0264 1.0000 Uiso R . . . . . . H321 H 0.8932 0.3664 0.1919 0.0264 1.0000 Uiso R . . . . . . H311 H 0.9007 0.3763 0.3297 0.0291 1.0000 Uiso R . . . . . . H312 H 0.6813 0.3661 0.3076 0.0291 1.0000 Uiso R . . . . . . H281 H 0.7539 0.5605 0.2623 0.0500 1.0000 Uiso R . . . . . . H241 H 0.6671 0.5504 0.5850 0.0333 1.0000 Uiso R . . . . . . H231 H 0.6126 0.6834 0.5884 0.0377 1.0000 Uiso R . . . . . . H221 H 0.6152 0.7584 0.4666 0.0389 1.0000 Uiso R . . . . . . H271 H 0.6633 0.7023 0.3355 0.0327 1.0000 Uiso R . . . . . . H291 H 0.7600 0.4404 0.4642 0.0500 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0269(14) 0.0268(14) 0.0210(12) -0.0070(10) 0.0014(10) -0.0002(11) C2 0.0247(14) 0.0385(15) 0.0134(11) 0.0027(10) 0.0000(10) -0.0022(11) C3 0.0232(13) 0.0255(13) 0.0210(12) 0.0065(10) -0.0001(10) -0.0007(10) C4 0.0158(11) 0.0206(12) 0.0184(11) 0.0012(10) 0.0018(9) -0.0005(9) C5 0.0142(11) 0.0199(12) 0.0178(12) 0.0038(9) 0.0002(9) -0.0012(9) C6 0.0226(13) 0.0169(12) 0.0234(13) -0.0001(10) 0.0016(10) 0.0006(10) N7 0.0219(10) 0.0113(9) 0.0207(10) 0.0048(8) 0.0014(8) -0.0009(8) N8 0.0250(11) 0.0145(9) 0.0139(9) 0.0050(7) 0.0015(8) 0.0010(8) C9 0.0174(12) 0.0168(11) 0.0195(11) 0.0036(9) 0.0028(9) -0.0036(9) C10 0.0293(13) 0.0133(10) 0.0192(10) -0.0001(9) 0.0016(10) -0.0026(10) C11 0.0258(13) 0.0167(11) 0.0172(11) 0.0026(9) 0.0008(9) -0.0008(10) C12 0.0248(13) 0.0140(11) 0.0170(11) -0.0035(9) 0.0007(9) -0.0009(9) C13 0.0151(11) 0.0213(12) 0.0160(11) -0.0025(9) 0.0030(9) 0.0003(9) N14 0.0219(10) 0.0171(10) 0.0120(9) -0.0020(7) 0.0005(7) 0.0010(8) N15 0.0221(11) 0.0238(11) 0.0149(10) -0.0017(8) -0.0006(8) 0.0011(8) C16 0.0129(11) 0.0240(13) 0.0190(12) 0.0006(10) 0.0018(9) 0.0026(9) C17 0.0153(11) 0.0260(13) 0.0175(11) 0.0041(10) 0.0027(9) 0.0042(10) C18 0.0269(13) 0.0228(13) 0.0257(13) 0.0024(10) 0.0033(11) 0.0033(10) C19 0.0352(15) 0.0285(14) 0.0325(14) 0.0131(12) 0.0101(12) 0.0069(12) C20 0.0288(14) 0.0456(16) 0.0172(12) 0.0125(11) 0.0043(10) 0.0098(12) C21 0.0224(13) 0.0421(15) 0.0147(11) 0.0030(11) 0.0016(9) 0.0067(11) C22 0.0289(15) 0.0242(13) 0.0323(14) -0.0080(11) 0.0078(11) -0.0033(10) C23 0.0251(14) 0.0401(16) 0.0237(13) -0.0119(11) 0.0063(10) -0.0045(11) C24 0.0212(12) 0.0371(15) 0.0146(11) 0.0008(10) 0.0033(9) -0.0033(11) C25 0.0107(11) 0.0289(13) 0.0178(11) 0.0004(10) 0.0000(9) -0.0027(9) C26 0.0132(12) 0.0253(12) 0.0170(11) 0.0000(10) 0.0028(9) -0.0005(9) C27 0.0263(13) 0.0274(13) 0.0241(12) -0.0010(11) 0.0045(10) -0.0018(11) N28 0.0202(10) 0.0182(10) 0.0137(9) -0.0012(8) 0.0031(8) -0.0010(8) N29 0.0183(11) 0.0225(10) 0.0145(9) 0.0056(8) 0.0027(8) 0.0009(8) C30 0.0130(11) 0.0229(12) 0.0146(11) 0.0023(9) -0.0010(9) -0.0006(9) C31 0.0234(12) 0.0178(12) 0.0188(11) 0.0029(9) -0.0019(9) 0.0009(9) C32 0.0226(12) 0.0176(11) 0.0159(11) -0.0017(9) 0.0014(9) 0.0023(9) C33 0.0222(12) 0.0190(11) 0.0159(10) -0.0002(9) 0.0026(9) -0.0025(9) C34 0.0144(11) 0.0164(11) 0.0183(11) -0.0023(9) -0.0010(9) 0.0018(8) N35 0.0227(11) 0.0156(10) 0.0138(9) -0.0024(7) 0.0012(8) -0.0004(8) N36 0.0200(10) 0.0156(10) 0.0173(9) -0.0016(8) -0.0009(8) 0.0031(8) C37 0.0116(11) 0.0208(12) 0.0183(11) -0.0018(10) 0.0008(9) 0.0041(9) C38 0.0162(12) 0.0202(12) 0.0170(11) -0.0019(9) 0.0000(9) 0.0005(9) C39 0.0239(14) 0.0251(14) 0.0274(13) 0.0056(11) 0.0018(11) -0.0007(10) C40 0.0215(13) 0.0441(16) 0.0227(13) 0.0131(12) 0.0063(10) 0.0030(12) C41 0.0238(14) 0.0496(18) 0.0147(12) -0.0032(12) 0.0009(10) 0.0103(12) C42 0.0212(13) 0.0257(13) 0.0218(12) -0.0064(10) -0.0021(10) 0.0058(10) S43 0.0223(3) 0.0134(3) 0.0146(3) 0.0005(2) -0.0020(2) -0.0006(2) O44 0.0230(9) 0.0234(9) 0.0360(9) -0.0110(7) 0.0036(7) -0.0032(7) O45 0.0276(9) 0.0246(9) 0.0205(8) 0.0047(7) 0.0029(7) 0.0015(7) O46 0.0403(11) 0.0169(9) 0.0315(10) -0.0049(8) -0.0132(8) 0.0027(8) O47 0.0359(11) 0.0312(10) 0.0277(9) 0.0113(8) -0.0069(8) -0.0039(8) S48 0.0214(3) 0.0112(3) 0.0143(3) 0.0009(2) 0.0024(2) -0.0007(2) O49 0.0548(12) 0.0155(8) 0.0140(7) 0.0002(6) 0.0013(7) -0.0035(8) O50 0.0230(9) 0.0341(10) 0.0325(9) 0.0101(8) -0.0018(7) -0.0013(8) O51 0.0369(11) 0.0453(11) 0.0325(10) 0.0117(9) 0.0164(8) 0.0083(9) O52 0.0441(11) 0.0160(9) 0.0261(9) -0.0009(7) -0.0067(8) -0.0021(8) O53 0.0310(10) 0.0270(10) 0.0233(9) 0.0083(8) 0.0034(8) 0.0024(8) O54 0.034(3) 0.049(3) 0.030(2) -0.008(3) -0.0028(18) 0.011(3) O55 0.035(3) 0.097(5) 0.031(2) -0.005(4) -0.0014(19) 0.008(4) O56 0.0541(14) 0.0784(17) 0.0338(11) -0.0113(11) 0.0105(10) -0.0150(12) O57 0.0436(12) 0.0489(12) 0.0325(10) -0.0106(9) 0.0044(9) 0.0006(9) O58 0.0416(12) 0.0816(17) 0.0259(10) -0.0111(10) -0.0025(9) 0.0124(12) O59 0.0284(11) 0.0750(16) 0.0321(11) -0.0254(11) 0.0046(9) -0.0090(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.08(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.404(4) yes C1 . C6 . 1.379(3) yes C1 . H11 . 0.950 no C2 . C3 . 1.376(4) yes C2 . H21 . 0.950 no C3 . C4 . 1.399(3) yes C3 . H31 . 0.951 no C4 . C5 . 1.390(3) yes C4 . N7 . 1.391(3) yes C5 . C6 . 1.398(3) yes C5 . N8 . 1.378(3) yes C6 . H61 . 0.951 no N7 . C9 . 1.323(3) yes N7 . H71 . 0.891 no N8 . C9 . 1.334(3) yes N8 . H81 . 0.827 no C9 . C10 . 1.492(3) yes C10 . C11 . 1.525(3) yes C10 . H101 . 0.951 no C10 . H102 . 0.952 no C11 . C12 . 1.525(3) yes C11 . H112 . 0.952 no C11 . H111 . 0.951 no C12 . C13 . 1.486(3) yes C12 . H121 . 0.951 no C12 . H122 . 0.952 no C13 . N14 . 1.331(3) yes C13 . N15 . 1.332(3) yes N14 . C17 . 1.390(3) yes N14 . H141 . 0.845 no N15 . C16 . 1.397(3) yes N15 . H151 . 0.905 no C16 . C17 . 1.378(3) yes C16 . C21 . 1.397(3) yes C17 . C18 . 1.402(3) yes C18 . C19 . 1.376(3) yes C18 . H181 . 0.950 no C19 . C20 . 1.409(4) yes C19 . H191 . 0.950 no C20 . C21 . 1.371(4) yes C20 . H201 . 0.950 no C21 . H211 . 0.950 no C22 . C23 . 1.404(4) yes C22 . C27 . 1.380(3) yes C22 . H221 . 0.950 no C23 . C24 . 1.375(4) yes C23 . H231 . 0.950 no C24 . C25 . 1.397(3) yes C24 . H241 . 0.950 no C25 . C26 . 1.394(3) yes C25 . N29 . 1.380(3) yes C26 . C27 . 1.375(4) yes C26 . N28 . 1.407(3) yes C27 . H271 . 0.950 no N28 . C30 . 1.318(3) yes N28 . H281 . 0.968 no N29 . C30 . 1.340(3) yes N29 . H291 . 0.786 no C30 . C31 . 1.497(3) yes C31 . C32 . 1.531(3) yes C31 . H311 . 0.952 no C31 . H312 . 0.951 no C32 . C33 . 1.531(3) yes C32 . H322 . 0.951 no C32 . H321 . 0.951 no C33 . C34 . 1.494(3) yes C33 . H331 . 0.951 no C33 . H332 . 0.951 no C34 . N35 . 1.328(3) yes C34 . N36 . 1.325(3) yes N35 . C38 . 1.380(3) yes N35 . H351 . 0.889 no N36 . C37 . 1.394(3) yes N36 . H361 . 0.907 no C37 . C38 . 1.400(3) yes C37 . C42 . 1.389(3) yes C38 . C39 . 1.385(3) yes C39 . C40 . 1.377(4) yes C39 . H391 . 0.951 no C40 . C41 . 1.394(4) yes C40 . H401 . 0.950 no C41 . C42 . 1.385(4) yes C41 . H411 . 0.950 no C42 . H421 . 0.951 no S43 . O44 . 1.4929(17) yes S43 . O45 . 1.4800(17) yes S43 . O46 . 1.4650(18) yes S43 . O47 . 1.4661(17) yes S48 . O49 . 1.4925(16) yes S48 . O50 . 1.4639(17) yes S48 . O51 . 1.4642(17) yes S48 . O52 . 1.4655(18) yes O53 . H532 . 0.959 no O53 . H531 . 0.960 no O54 . H542 . 0.960 no O54 . H541 . 0.958 no O55 . H551 . 0.960 no O55 . H552 . 0.958 no O56 . H562 . 0.960 no O56 . H561 . 0.958 no O57 . H571 . 0.959 no O57 . H572 . 0.959 no O58 . H582 . 0.959 no O58 . H581 . 0.960 no O59 . H592 . 0.960 no O59 . H591 . 0.959 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 122.0(2) yes C2 . C1 . H11 . 118.7 no C6 . C1 . H11 . 119.3 no C1 . C2 . C3 . 121.8(2) yes C1 . C2 . H21 . 119.0 no C3 . C2 . H21 . 119.2 no C2 . C3 . C4 . 116.8(2) yes C2 . C3 . H31 . 121.8 no C4 . C3 . H31 . 121.4 no C3 . C4 . C5 . 121.1(2) yes C3 . C4 . N7 . 132.6(2) yes C5 . C4 . N7 . 106.2(2) yes C4 . C5 . C6 . 122.2(2) yes C4 . C5 . N8 . 106.8(2) yes C6 . C5 . N8 . 131.0(2) yes C5 . C6 . C1 . 116.1(2) yes C5 . C6 . H61 . 122.3 no C1 . C6 . H61 . 121.6 no C4 . N7 . C9 . 108.51(18) yes C4 . N7 . H71 . 129.1 no C9 . N7 . H71 . 122.3 no C5 . N8 . C9 . 108.47(19) yes C5 . N8 . H81 . 125.2 no C9 . N8 . H81 . 126.0 no N8 . C9 . N7 . 110.0(2) yes N8 . C9 . C10 . 125.79(19) yes N7 . C9 . C10 . 124.2(2) yes C9 . C10 . C11 . 111.36(18) yes C9 . C10 . H101 . 109.1 no C11 . C10 . H101 . 108.9 no C9 . C10 . H102 . 108.8 no C11 . C10 . H102 . 109.0 no H101 . C10 . H102 . 109.5 no C10 . C11 . C12 . 112.39(18) yes C10 . C11 . H112 . 108.7 no C12 . C11 . H112 . 109.3 no C10 . C11 . H111 . 108.6 no C12 . C11 . H111 . 108.4 no H112 . C11 . H111 . 109.5 no C11 . C12 . C13 . 110.73(17) yes C11 . C12 . H121 . 108.7 no C13 . C12 . H121 . 108.8 no C11 . C12 . H122 . 109.6 no C13 . C12 . H122 . 109.5 no H121 . C12 . H122 . 109.5 no C12 . C13 . N14 . 125.0(2) yes C12 . C13 . N15 . 125.6(2) yes N14 . C13 . N15 . 109.3(2) yes C13 . N14 . C17 . 108.85(19) yes C13 . N14 . H141 . 140.2 no C17 . N14 . H141 . 110.3 no C13 . N15 . C16 . 108.7(2) yes C13 . N15 . H151 . 128.5 no C16 . N15 . H151 . 122.6 no N15 . C16 . C17 . 106.36(19) yes N15 . C16 . C21 . 132.0(2) yes C17 . C16 . C21 . 121.6(2) yes N14 . C17 . C16 . 106.7(2) yes N14 . C17 . C18 . 130.7(2) yes C16 . C17 . C18 . 122.5(2) yes C17 . C18 . C19 . 115.7(2) yes C17 . C18 . H181 . 122.0 no C19 . C18 . H181 . 122.2 no C18 . C19 . C20 . 121.5(2) yes C18 . C19 . H191 . 118.6 no C20 . C19 . H191 . 119.8 no C19 . C20 . C21 . 122.5(2) yes C19 . C20 . H201 . 117.9 no C21 . C20 . H201 . 119.6 no C16 . C21 . C20 . 116.1(2) yes C16 . C21 . H211 . 122.0 no C20 . C21 . H211 . 122.0 no C23 . C22 . C27 . 121.3(2) yes C23 . C22 . H221 . 119.5 no C27 . C22 . H221 . 119.2 no C22 . C23 . C24 . 122.1(2) yes C22 . C23 . H231 . 118.8 no C24 . C23 . H231 . 119.1 no C23 . C24 . C25 . 116.2(2) yes C23 . C24 . H241 . 122.1 no C25 . C24 . H241 . 121.7 no C24 . C25 . C26 . 121.5(2) yes C24 . C25 . N29 . 131.7(2) yes C26 . C25 . N29 . 106.8(2) yes C25 . C26 . C27 . 121.9(2) yes C25 . C26 . N28 . 105.4(2) yes C27 . C26 . N28 . 132.7(2) yes C22 . C27 . C26 . 117.0(2) yes C22 . C27 . H271 . 121.7 no C26 . C27 . H271 . 121.4 no C26 . N28 . C30 . 109.47(19) yes C26 . N28 . H281 . 121.5 no C30 . N28 . H281 . 128.2 no C25 . N29 . C30 . 109.3(2) yes C25 . N29 . H291 . 124.4 no C30 . N29 . H291 . 124.7 no N29 . C30 . N28 . 109.1(2) yes N29 . C30 . C31 . 122.7(2) yes N28 . C30 . C31 . 128.2(2) yes C30 . C31 . C32 . 115.93(19) yes C30 . C31 . H311 . 108.0 no C32 . C31 . H311 . 108.0 no C30 . C31 . H312 . 107.7 no C32 . C31 . H312 . 107.5 no H311 . C31 . H312 . 109.6 no C31 . C32 . C33 . 112.91(18) yes C31 . C32 . H322 . 108.5 no C33 . C32 . H322 . 108.7 no C31 . C32 . H321 . 108.5 no C33 . C32 . H321 . 108.7 no H322 . C32 . H321 . 109.4 no C32 . C33 . C34 . 112.11(18) yes C32 . C33 . H331 . 108.9 no C34 . C33 . H331 . 108.7 no C32 . C33 . H332 . 108.8 no C34 . C33 . H332 . 108.8 no H331 . C33 . H332 . 109.4 no C33 . C34 . N35 . 122.51(19) yes C33 . C34 . N36 . 127.1(2) yes N35 . C34 . N36 . 110.33(19) yes C34 . N35 . C38 . 108.90(18) yes C34 . N35 . H351 . 126.7 no C38 . N35 . H351 . 123.2 no C34 . N36 . C37 . 108.20(19) yes C34 . N36 . H361 . 127.7 no C37 . N36 . H361 . 111.3 no N36 . C37 . C38 . 106.36(19) yes N36 . C37 . C42 . 132.3(2) yes C38 . C37 . C42 . 121.3(2) yes C37 . C38 . N35 . 106.2(2) yes C37 . C38 . C39 . 121.8(2) yes N35 . C38 . C39 . 132.0(2) yes C38 . C39 . C40 . 116.7(2) yes C38 . C39 . H391 . 121.2 no C40 . C39 . H391 . 122.1 no C39 . C40 . C41 . 121.7(2) yes C39 . C40 . H401 . 118.9 no C41 . C40 . H401 . 119.3 no C40 . C41 . C42 . 122.0(2) yes C40 . C41 . H411 . 118.9 no C42 . C41 . H411 . 119.2 no C37 . C42 . C41 . 116.5(2) yes C37 . C42 . H421 . 121.6 no C41 . C42 . H421 . 121.9 no O44 . S43 . O45 . 107.80(10) yes O44 . S43 . O46 . 108.37(10) yes O45 . S43 . O46 . 110.01(11) yes O44 . S43 . O47 . 109.45(11) yes O45 . S43 . O47 . 110.25(10) yes O46 . S43 . O47 . 110.89(10) yes O49 . S48 . O50 . 109.18(11) yes O49 . S48 . O51 . 108.80(11) yes O50 . S48 . O51 . 109.29(10) yes O49 . S48 . O52 . 107.73(10) yes O50 . S48 . O52 . 110.67(11) yes O51 . S48 . O52 . 111.13(11) yes H532 . O53 . H531 . 104.5 no H542 . O54 . H541 . 104.4 no H551 . O55 . H552 . 104.4 no H562 . O56 . H561 . 104.4 no H571 . O57 . H572 . 104.4 no H582 . O58 . H581 . 104.6 no H592 . O59 . H591 . 104.6 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 O56 . H562 . O54 1_455 155 0.96 1.76 2.662(3) yes O56 . H562 . O55 1_455 167 0.96 1.88 2.824(3) yes O56 . H561 . O47 2_564 147 0.96 2.15 2.993(3) yes O53 . H532 . O51 2_465 159 0.96 1.81 2.723(3) yes O53 . H531 . O50 2_565 158 0.96 1.85 2.767(3) yes O59 . H592 . O45 . 168 0.96 1.84 2.790(3) yes O59 . H591 . O44 1_655 149 0.96 1.90 2.761(3) yes O58 . H582 . O50 2_465 177 0.96 1.84 2.796(3) yes O58 . H581 . O57 1_455 178 0.96 1.83 2.790(3) yes O57 . H571 . O56 . 164 0.96 1.82 2.752(3) yes O57 . H572 . O51 2_465 164 0.96 1.89 2.825(3) yes O55 . H551 . O47 2_564 173 0.96 1.92 2.873(3) yes O54 . H542 . O47 2_564 176 0.96 1.96 2.921(3) yes O55 . H542 . O47 2_564 136 1.12 1.96 2.873(3) yes O55 . H552 . O58 1_655 172 0.96 1.78 2.732(3) yes O54 . H541 . O58 1_655 177 0.96 1.85 2.811(3) yes O55 . H541 . O58 1_655 135 1.09 1.85 2.732(3) yes N14 . H141 . O45 2_465 166 0.84 1.95 2.775(3) yes N15 . H151 . O59 1_445 152 0.91 1.85 2.686(3) yes N8 . H81 . O44 2_465 167 0.83 1.87 2.685(3) yes C3 . H31 . O46 1_546 143 0.95 2.59 3.399(3) yes C2 . H21 . O44 1_546 135 0.95 2.60 3.342(3) yes N7 . H71 . O52 1_446 175 0.89 1.79 2.676(3) yes N35 . H351 . O49 . 159 0.89 1.80 2.644(3) yes N36 . H361 . O46 2_564 141 0.91 1.91 2.676(3) yes N28 . H281 . O49 . 173 0.97 1.78 2.743(3) yes C27 . H271 . O52 . 141 0.95 2.51 3.303(3) yes N29 . H291 . O53 . 156 0.79 1.93 2.665(3) yes _chemical_name_common '1,2-bis(benzimidazolonium)ethane sulphate trihydrate' #==END data_(4)2(HPO4)(H2PO4)2 _database_code_depnum_ccdc_archive 'CCDC 848426' #TrackingRef '- bzimphos.cif' _audit_creation_date 2011-09-02 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.08.21 svn.r1945, GUI svn.r3824) ; _chemical_name_common ; Bis(1,5-bis(benzimidazolonium)pentane) bis(dihydrogenophosphate)monohydrogenophosphate tetrahydrate ; _chemical_name_systematic ; Bis(1,5-bis(benzimidazolonium)pentane) bis(dihydrogenophosphate)monohydrogenophosphate tetrahydrate ; _chemical_formula_moiety 'O4 H P, 2(O4 H2 P), 2(C19 H22 N4), 4(H2 O)' _chemical_formula_sum 'C38 H57 N8 O16 P3' _chemical_formula_weight 974.83 _chemical_melting_point ? _chemical_oxdiff_formula 'C38 H57 N8 O16 P3' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 9.8599(5) _cell_length_b 12.9049(8) _cell_length_c 18.8173(6) _cell_angle_alpha 95.255(4) _cell_angle_beta 103.115(4) _cell_angle_gamma 102.980(5) _cell_volume 2246.5(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 13904 _cell_measurement_temperature 200.0 _cell_measurement_theta_max 73.3434 _cell_measurement_theta_min 3.5522 _exptl_absorpt_coefficient_mu 1.900 _exptl_absorpt_correction_T_max 0.887 _exptl_absorpt_correction_T_min 0.646 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 1028 _exptl_crystal_size_max 0.3915 _exptl_crystal_size_mid 0.1828 _exptl_crystal_size_min 0.0669 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_unetI/netI 0.0271 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 21035 _diffrn_reflns_theta_full 73.50 _diffrn_reflns_theta_max 73.50 _diffrn_reflns_theta_min 3.56 _diffrn_ambient_temperature 200.0 _diffrn_detector_area_resol_mean 10.4679 _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -71.00 42.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 77.0000 120.0000 113 #__ type_ start__ end____ width___ exp.time_ 2 omega -73.00 43.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 77.0000 -120.0000 116 #__ type_ start__ end____ width___ exp.time_ 3 omega -63.00 43.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 77.0000 0.0000 106 #__ type_ start__ end____ width___ exp.time_ 4 omega -63.00 -33.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 77.0000 -30.0000 30 #__ type_ start__ end____ width___ exp.time_ 5 omega -6.00 19.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 37.5615 98.0000 -179.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega 69.00 95.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 37.5615 38.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 7 omega 68.00 94.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - 37.5615 38.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 39.00 71.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -45.0000 -120.0000 32 #__ type_ start__ end____ width___ exp.time_ 9 omega 105.00 154.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 111.0000 -180.0000 49 #__ type_ start__ end____ width___ exp.time_ 10 omega 30.00 110.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -112.0000 174.0000 80 #__ type_ start__ end____ width___ exp.time_ 11 omega 57.00 129.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -77.0000 -180.0000 72 #__ type_ start__ end____ width___ exp.time_ 12 omega 75.00 122.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 77.0000 -120.0000 47 #__ type_ start__ end____ width___ exp.time_ 13 omega 31.00 59.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -45.0000 -180.0000 28 #__ type_ start__ end____ width___ exp.time_ 14 omega 34.00 60.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -45.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega 36.00 63.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -45.0000 -90.0000 27 #__ type_ start__ end____ width___ exp.time_ 16 omega 111.00 178.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 111.0000 150.0000 67 #__ type_ start__ end____ width___ exp.time_ 17 omega 109.00 158.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 111.0000 -150.0000 49 #__ type_ start__ end____ width___ exp.time_ 18 omega 32.00 76.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -45.0000 120.0000 44 #__ type_ start__ end____ width___ exp.time_ 19 omega 35.00 74.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -45.0000 60.0000 39 #__ type_ start__ end____ width___ exp.time_ 20 omega 27.00 174.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 0.0000 -150.0000 147 #__ type_ start__ end____ width___ exp.time_ 21 omega 62.00 101.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -111.0000 108.0000 39 #__ type_ start__ end____ width___ exp.time_ 22 omega 40.00 125.00 1.0000 5.0000 omega____ theta____ kappa____ phi______ frames - 109.7499 -133.0000 32.0000 85 #__ type_ start__ end____ width___ exp.time_ 23 omega -122.00 -1.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 -77.0000 30.0000 121 #__ type_ start__ end____ width___ exp.time_ 24 omega -122.00 -1.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 -77.0000 90.0000 121 #__ type_ start__ end____ width___ exp.time_ 25 omega -122.00 -1.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 -77.0000 -90.0000 121 #__ type_ start__ end____ width___ exp.time_ 26 omega -74.00 46.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 77.0000 30.0000 120 #__ type_ start__ end____ width___ exp.time_ 27 omega -117.00 -6.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 -38.0000 -60.0000 111 #__ type_ start__ end____ width___ exp.time_ 28 omega -117.00 -86.00 1.0000 1.5000 omega____ theta____ kappa____ phi______ frames - -37.5615 -38.0000 120.0000 31 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0666590000 _diffrn_orient_matrix_UB_12 -0.0967391000 _diffrn_orient_matrix_UB_13 -0.0047580000 _diffrn_orient_matrix_UB_21 -0.1402590000 _diffrn_orient_matrix_UB_22 -0.0749081000 _diffrn_orient_matrix_UB_23 0.0071754000 _diffrn_orient_matrix_UB_31 -0.0581588000 _diffrn_orient_matrix_UB_32 -0.0196225000 _diffrn_orient_matrix_UB_33 -0.0845899000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _reflns_number_gt 8104 _reflns_number_total 8756 _reflns_odcompleteness_completeness 99.81 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.465 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.057 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 594 _refine_ls_number_reflns 8756 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0385 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.9508P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1075 _refine_ls_wR_factor_ref 0.1114 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Except for HW1B the positions of all hydrogen atoms are suitable for hydrogen bond formation with neighbouring atoms. Some density was found in the difference Fourier map prior to the introduction of the H atoms for all hydrogen atoms. However these maps were not as clear for OW2 OW3 and especially OW1. The quality of the data did not allow to freely refined the hydrogen of the waters molecules even using geometrical restrains. The hydrogen positions were calculated geometrically and the hydrogen atoms were allowed to ride on the parent atom. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.02794(4) 0.32986(3) 0.76035(2) 0.02441(10) Uani 1 1 d . . . P6 P 0.93977(4) 0.63390(3) 0.73043(2) 0.02509(10) Uani 1 1 d . . . P11 P 1.01768(4) 1.01033(3) 0.76104(2) 0.02506(10) Uani 1 1 d . . . O8 O 1.08394(13) 0.60865(10) 0.72339(7) 0.0356(3) Uani 1 1 d . . . H8 H 1.0828 0.5455 0.7313 0.053 Uiso 1 1 calc R . . O12 O 1.07881(14) 1.08719(10) 0.83673(6) 0.0361(3) Uani 1 1 d . . . H12 H 1.0721 1.1496 0.8304 0.054 Uiso 1 1 calc R . . O2 O 0.12901(12) 0.43408(9) 0.75431(7) 0.0322(3) Uani 1 1 d . . . O3 O 0.08328(14) 0.28447(9) 0.83052(6) 0.0312(3) Uani 1 1 d . . . O14 O 0.85588(13) 0.97922(10) 0.74451(8) 0.0394(3) Uani 1 1 d . . . O15 O 1.06959(14) 1.07166(10) 0.70075(7) 0.0361(3) Uani 1 1 d . . . H15 H 1.0420 1.1287 0.6998 0.054 Uiso 1 1 calc R . . O10 O 0.86959(14) 0.66631(10) 0.65946(6) 0.0349(3) Uani 1 1 d . . . O5 O -0.12042(13) 0.35276(9) 0.76543(8) 0.0370(3) Uani 1 1 d . . . H5 H -0.1173 0.4177 0.7620 0.056 Uiso 1 1 calc R . . O7 O 0.98208(15) 0.73184(9) 0.79470(6) 0.0361(3) Uani 1 1 d . . . H7 H 1.0131 0.7890 0.7789 0.054 Uiso 1 1 calc R . . O13 O 1.08593(13) 0.91647(9) 0.76597(7) 0.0343(3) Uani 1 1 d . . . O9 O 0.84976(13) 0.54276(9) 0.75728(7) 0.0337(3) Uani 1 1 d . . . N8B N 0.25708(14) 0.88502(11) 0.68080(8) 0.0297(3) Uani 1 1 d . . . H8B H 0.1953 0.8980 0.7055 0.036 Uiso 1 1 calc R . . N23B N 1.00291(14) 0.66338(11) 1.04814(7) 0.0264(3) Uani 1 1 d . . . H23B H 0.9806 0.6699 1.0907 0.032 Uiso 1 1 calc R . . N23A N 0.71986(14) 0.08237(11) 0.81751(7) 0.0279(3) Uani 1 1 d . . . H23A H 0.7712 0.0556 0.7915 0.034 Uiso 1 1 calc R . . C7B C 0.25145(17) 0.89990(13) 0.60838(9) 0.0278(3) Uani 1 1 d . . . C21A C 0.8210(2) 0.03972(15) 0.94451(10) 0.0377(4) Uani 1 1 d . . . H21A H 0.8911 0.0063 0.9324 0.045 Uiso 1 1 calc R . . C2A C -0.11451(17) 0.36175(12) 0.53672(8) 0.0253(3) Uani 1 1 d . . . N1A N 0.00169(14) 0.32133(11) 0.56602(7) 0.0262(3) Uani 1 1 d . . . H1A H 0.0231 0.3040 0.6106 0.031 Uiso 1 1 calc R . . C20B C 1.31372(18) 0.54548(15) 1.04612(10) 0.0360(4) Uani 1 1 d . . . H20B H 1.3852 0.5170 1.0748 0.043 Uiso 1 1 calc R . . C10B C 0.41237(19) 0.82412(15) 0.78374(10) 0.0348(4) Uani 1 1 d . . . H10C H 0.3323 0.7686 0.7918 0.042 Uiso 1 1 calc R . . H10D H 0.4255 0.8900 0.8186 0.042 Uiso 1 1 calc R . . C6A C -0.21094(18) 0.41718(14) 0.41970(9) 0.0310(3) Uani 1 1 d . . . H6A H -0.2075 0.4281 0.3708 0.037 Uiso 1 1 calc R . . N16A N 0.56118(14) 0.16088(11) 0.84583(7) 0.0291(3) Uani 1 1 d . . . H16A H 0.4917 0.1942 0.8415 0.035 Uiso 1 1 calc R . . C13A C 0.4498(2) 0.20182(16) 0.69749(9) 0.0371(4) Uani 1 1 d . . . H13A H 0.4774 0.2731 0.7287 0.044 Uiso 1 1 calc R . . H13B H 0.3674 0.1567 0.7114 0.044 Uiso 1 1 calc R . . N8A N 0.01264(14) 0.34577(11) 0.45435(7) 0.0252(3) Uani 1 1 d . . . H8A H 0.0427 0.3472 0.4138 0.030 Uiso 1 1 calc R . . C18B C 1.20880(18) 0.59173(15) 0.92743(9) 0.0340(4) Uani 1 1 d . . . H18B H 1.2058 0.5954 0.8769 0.041 Uiso 1 1 calc R . . C7A C -0.10786(16) 0.37725(12) 0.46501(8) 0.0248(3) Uani 1 1 d . . . C17A C 0.62964(18) 0.12978(13) 0.91013(9) 0.0298(3) Uani 1 1 d . . . C3B C 0.39733(19) 0.87524(15) 0.52322(10) 0.0358(4) Uani 1 1 d . . . H3B H 0.4785 0.8557 0.5123 0.043 Uiso 1 1 calc R . . C3A C -0.22167(18) 0.38615(14) 0.56709(9) 0.0315(3) Uani 1 1 d . . . H3A H -0.2246 0.3763 0.6162 0.038 Uiso 1 1 calc R . . C19B C 1.30936(19) 0.55063(16) 0.97157(10) 0.0370(4) Uani 1 1 d . . . H19B H 1.3774 0.5252 0.9510 0.044 Uiso 1 1 calc R . . C22A C 0.73145(17) 0.08001(13) 0.89203(9) 0.0281(3) Uani 1 1 d . . . C14A C 0.57538(17) 0.15038(14) 0.71368(9) 0.0289(3) Uani 1 1 d . . . H14A H 0.5495 0.0806 0.6809 0.035 Uiso 1 1 calc R . . H14B H 0.6592 0.1972 0.7019 0.035 Uiso 1 1 calc R . . N16B N 0.99845(15) 0.67152(12) 0.93315(7) 0.0299(3) Uani 1 1 d . . . H16B H 0.9725 0.6845 0.8876 0.036 Uiso 1 1 calc R . . C13B C 0.7378(2) 0.73814(16) 0.89588(9) 0.0354(4) Uani 1 1 d . . . H13C H 0.8071 0.7890 0.8767 0.042 Uiso 1 1 calc R . . H13D H 0.7211 0.6659 0.8676 0.042 Uiso 1 1 calc R . . C2B C 0.36956(16) 0.87022(13) 0.59189(9) 0.0275(3) Uani 1 1 d . . . C6B C 0.15517(19) 0.93583(14) 0.55651(10) 0.0357(4) Uani 1 1 d . . . H6B H 0.0750 0.9567 0.5677 0.043 Uiso 1 1 calc R . . N1B N 0.44160(14) 0.83829(11) 0.65512(7) 0.0277(3) Uani 1 1 d . . . H1B H 0.5205 0.8155 0.6600 0.033 Uiso 1 1 calc R . . C4B C 0.3012(2) 0.91001(16) 0.47152(10) 0.0414(4) Uani 1 1 d . . . H4B H 0.3161 0.9139 0.4236 0.050 Uiso 1 1 calc R . . C11A C 0.2685(2) 0.25937(17) 0.60462(10) 0.0374(4) Uani 1 1 d . . . H11A H 0.1932 0.2103 0.6213 0.045 Uiso 1 1 calc R . . H11B H 0.2924 0.3303 0.6358 0.045 Uiso 1 1 calc R . . C4A C -0.32334(19) 0.42531(15) 0.52216(10) 0.0361(4) Uani 1 1 d . . . H4A H -0.3987 0.4428 0.5406 0.043 Uiso 1 1 calc R . . C20A C 0.8029(2) 0.05072(17) 1.01522(11) 0.0442(4) Uani 1 1 d . . . H20A H 0.8618 0.0240 1.0527 0.053 Uiso 1 1 calc R . . C11B C 0.54901(19) 0.78516(15) 0.80142(9) 0.0339(4) Uani 1 1 d . . . H11C H 0.6273 0.8375 0.7892 0.041 Uiso 1 1 calc R . . H11D H 0.5330 0.7155 0.7699 0.041 Uiso 1 1 calc R . . C21B C 1.21695(18) 0.58068(14) 1.07918(9) 0.0314(3) Uani 1 1 d . . . H21B H 1.2198 0.5765 1.1296 0.038 Uiso 1 1 calc R . . C10A C 0.20710(18) 0.27179(14) 0.52537(9) 0.0308(3) Uani 1 1 d . . . H10A H 0.2812 0.3219 0.5087 0.037 Uiso 1 1 calc R . . H10B H 0.1834 0.2012 0.4938 0.037 Uiso 1 1 calc R . . C14B C 0.80560(19) 0.73541(15) 0.97686(9) 0.0329(4) Uani 1 1 d . . . H14C H 0.8338 0.8092 1.0045 0.039 Uiso 1 1 calc R . . H14D H 0.7335 0.6907 0.9979 0.039 Uiso 1 1 calc R . . C19A C 0.7002(2) 0.10018(18) 1.03287(11) 0.0476(5) Uani 1 1 d . . . H19A H 0.6910 0.1058 1.0821 0.057 Uiso 1 1 calc R . . C5A C -0.31838(19) 0.44005(15) 0.44986(10) 0.0363(4) Uani 1 1 d . . . H5A H -0.3912 0.4666 0.4206 0.044 Uiso 1 1 calc R . . C12B C 0.59643(18) 0.77102(14) 0.88195(9) 0.0323(4) Uani 1 1 d . . . H12C H 0.6087 0.8394 0.9141 0.039 Uiso 1 1 calc R . . H12D H 0.5217 0.7151 0.8939 0.039 Uiso 1 1 calc R . . C9B C 0.37140(17) 0.84784(13) 0.70712(9) 0.0278(3) Uani 1 1 d . . . C12A C 0.40187(17) 0.21621(14) 0.61708(9) 0.0307(3) Uani 1 1 d . . . H12A H 0.4804 0.2669 0.6038 0.037 Uiso 1 1 calc R . . H12B H 0.3806 0.1463 0.5850 0.037 Uiso 1 1 calc R . . C5B C 0.1825(2) 0.93963(16) 0.48769(10) 0.0411(4) Uani 1 1 d . . . H5B H 0.1187 0.9630 0.4504 0.049 Uiso 1 1 calc R . . C9A C 0.07542(17) 0.31306(12) 0.51565(8) 0.0251(3) Uani 1 1 d . . . C18A C 0.6119(2) 0.14104(17) 0.98127(10) 0.0420(4) Uani 1 1 d . . . H18A H 0.5427 0.1751 0.9937 0.050 Uiso 1 1 calc R . . C15B C 0.93472(18) 0.69107(13) 0.98625(8) 0.0273(3) Uani 1 1 d . . . O4 O -0.00279(15) 0.24566(9) 0.69244(6) 0.0342(3) Uani 1 1 d . . . C15A C 0.61789(16) 0.13192(12) 0.79165(9) 0.0261(3) Uani 1 1 d . . . C17B C 1.11206(17) 0.62755(13) 0.96063(8) 0.0282(3) Uani 1 1 d . . . C22B C 1.11519(17) 0.62245(12) 1.03483(8) 0.0258(3) Uani 1 1 d . . . OW4 O 0.69413(13) 0.80368(12) 0.64640(8) 0.0419(3) Uani 1 1 d G . . HW4A H 0.7565 0.8567 0.6771 0.063 Uiso 1 1 d G . . HW4B H 0.7504 0.7603 0.6495 0.063 Uiso 1 1 d G . . OW3 O 0.38456(14) 0.28867(12) 0.86355(8) 0.0474(3) Uani 1 1 d . . . HW3A H 0.2943 0.2780 0.8637 0.071 Uiso 1 1 d R . . HW3B H 0.4081 0.3422 0.8400 0.071 Uiso 1 1 d R . . OW1 O 0.56728(18) 0.51883(19) 0.69728(10) 0.0791(6) Uani 1 1 d . . . HW1A H 0.6487 0.5198 0.7262 0.119 Uiso 1 1 d R . . HW1B H 0.5766 0.4869 0.6577 0.119 Uiso 1 1 d R . . OW2 O 0.42133(16) 0.48527(14) 0.80988(9) 0.0581(4) Uani 1 1 d . . . HW2A H 0.3390 0.4857 0.7842 0.087 Uiso 1 1 d R . . HW2B H 0.4839 0.5197 0.7902 0.087 Uiso 1 1 d 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 P1 0.0360(2) 0.02250(19) 0.02051(19) 0.00645(14) 0.01153(15) 0.01354(16) P6 0.0351(2) 0.0242(2) 0.02229(19) 0.00835(15) 0.01173(16) 0.01408(16) P11 0.0292(2) 0.02215(19) 0.0304(2) 0.00644(15) 0.01372(16) 0.01252(15) O8 0.0387(6) 0.0322(6) 0.0481(7) 0.0198(5) 0.0222(6) 0.0167(5) O12 0.0498(7) 0.0315(6) 0.0296(6) 0.0079(5) 0.0079(5) 0.0164(5) O2 0.0325(6) 0.0294(6) 0.0418(7) 0.0136(5) 0.0142(5) 0.0144(5) O3 0.0520(7) 0.0268(6) 0.0192(5) 0.0049(4) 0.0109(5) 0.0163(5) O14 0.0311(6) 0.0364(7) 0.0536(8) -0.0039(6) 0.0162(6) 0.0132(5) O15 0.0548(8) 0.0311(6) 0.0366(6) 0.0136(5) 0.0249(6) 0.0229(6) O10 0.0504(7) 0.0406(7) 0.0231(6) 0.0080(5) 0.0121(5) 0.0267(6) O5 0.0387(6) 0.0251(6) 0.0560(8) 0.0116(5) 0.0242(6) 0.0116(5) O7 0.0641(8) 0.0267(6) 0.0217(6) 0.0084(5) 0.0165(5) 0.0126(6) O13 0.0387(6) 0.0264(6) 0.0510(7) 0.0149(5) 0.0240(6) 0.0183(5) O9 0.0349(6) 0.0289(6) 0.0472(7) 0.0147(5) 0.0197(5) 0.0153(5) N8B 0.0265(6) 0.0353(7) 0.0339(7) 0.0078(6) 0.0125(6) 0.0150(6) N23B 0.0335(7) 0.0316(7) 0.0172(6) 0.0050(5) 0.0092(5) 0.0114(5) N23A 0.0279(6) 0.0338(7) 0.0272(7) 0.0058(5) 0.0094(5) 0.0151(5) C7B 0.0255(7) 0.0262(7) 0.0322(8) 0.0029(6) 0.0076(6) 0.0074(6) C21A 0.0398(9) 0.0391(9) 0.0355(9) 0.0096(7) 0.0057(7) 0.0148(8) C2A 0.0281(7) 0.0259(7) 0.0213(7) 0.0050(6) 0.0052(6) 0.0063(6) N1A 0.0328(7) 0.0312(7) 0.0182(6) 0.0087(5) 0.0076(5) 0.0122(5) C20B 0.0303(8) 0.0449(10) 0.0325(9) 0.0067(7) 0.0037(7) 0.0129(7) C10B 0.0328(8) 0.0440(10) 0.0347(9) 0.0113(7) 0.0134(7) 0.0168(7) C6A 0.0340(8) 0.0355(8) 0.0228(8) 0.0074(6) 0.0028(6) 0.0109(7) N16A 0.0278(6) 0.0341(7) 0.0303(7) 0.0047(6) 0.0098(5) 0.0153(5) C13A 0.0384(9) 0.0536(11) 0.0276(8) 0.0103(8) 0.0094(7) 0.0258(8) N8A 0.0290(6) 0.0308(7) 0.0178(6) 0.0057(5) 0.0072(5) 0.0094(5) C18B 0.0359(9) 0.0449(10) 0.0245(8) 0.0056(7) 0.0129(7) 0.0117(7) C7A 0.0269(7) 0.0257(7) 0.0212(7) 0.0033(6) 0.0052(6) 0.0066(6) C17A 0.0302(8) 0.0318(8) 0.0289(8) 0.0044(6) 0.0094(6) 0.0091(6) C3B 0.0359(9) 0.0399(9) 0.0332(9) 0.0000(7) 0.0123(7) 0.0114(7) C3A 0.0356(8) 0.0357(9) 0.0272(8) 0.0076(7) 0.0131(7) 0.0105(7) C19B 0.0315(8) 0.0475(10) 0.0346(9) 0.0034(8) 0.0118(7) 0.0132(8) C22A 0.0294(8) 0.0283(8) 0.0279(8) 0.0052(6) 0.0078(6) 0.0085(6) C14A 0.0275(7) 0.0351(8) 0.0271(8) 0.0061(6) 0.0082(6) 0.0122(6) N16B 0.0371(7) 0.0397(8) 0.0180(6) 0.0095(5) 0.0097(5) 0.0155(6) C13B 0.0421(9) 0.0469(10) 0.0262(8) 0.0110(7) 0.0124(7) 0.0238(8) C2B 0.0245(7) 0.0264(7) 0.0311(8) 0.0011(6) 0.0061(6) 0.0078(6) C6B 0.0311(8) 0.0370(9) 0.0405(10) 0.0055(7) 0.0055(7) 0.0154(7) N1B 0.0234(6) 0.0307(7) 0.0321(7) 0.0035(5) 0.0082(5) 0.0122(5) C4B 0.0495(11) 0.0450(10) 0.0295(9) 0.0037(8) 0.0103(8) 0.0118(9) C11A 0.0384(9) 0.0563(11) 0.0273(8) 0.0134(8) 0.0113(7) 0.0260(8) C4A 0.0325(8) 0.0431(10) 0.0371(9) 0.0081(8) 0.0129(7) 0.0138(7) C20A 0.0495(11) 0.0490(11) 0.0323(9) 0.0140(8) 0.0029(8) 0.0133(9) C11B 0.0387(9) 0.0402(9) 0.0304(8) 0.0099(7) 0.0118(7) 0.0201(7) C21B 0.0326(8) 0.0390(9) 0.0212(7) 0.0058(6) 0.0037(6) 0.0087(7) C10A 0.0351(8) 0.0375(9) 0.0249(8) 0.0076(7) 0.0096(7) 0.0163(7) C14B 0.0415(9) 0.0392(9) 0.0252(8) 0.0088(7) 0.0124(7) 0.0194(7) C19A 0.0579(12) 0.0576(12) 0.0267(9) 0.0076(8) 0.0140(8) 0.0098(10) C5A 0.0325(8) 0.0433(10) 0.0346(9) 0.0087(7) 0.0040(7) 0.0164(7) C12B 0.0359(9) 0.0364(9) 0.0310(8) 0.0103(7) 0.0132(7) 0.0153(7) C9B 0.0260(7) 0.0264(7) 0.0331(8) 0.0046(6) 0.0096(6) 0.0090(6) C12A 0.0295(8) 0.0395(9) 0.0265(8) 0.0084(7) 0.0080(6) 0.0134(7) C5B 0.0436(10) 0.0426(10) 0.0348(9) 0.0062(8) -0.0002(8) 0.0163(8) C9A 0.0302(8) 0.0262(7) 0.0198(7) 0.0048(6) 0.0063(6) 0.0082(6) C18A 0.0465(10) 0.0509(11) 0.0327(9) 0.0033(8) 0.0174(8) 0.0144(9) C15B 0.0357(8) 0.0295(8) 0.0197(7) 0.0065(6) 0.0093(6) 0.0110(6) O4 0.0595(8) 0.0310(6) 0.0185(5) 0.0070(4) 0.0101(5) 0.0227(5) C15A 0.0238(7) 0.0269(7) 0.0291(8) 0.0041(6) 0.0077(6) 0.0084(6) C17B 0.0304(8) 0.0339(8) 0.0208(7) 0.0054(6) 0.0071(6) 0.0081(6) C22B 0.0284(7) 0.0284(8) 0.0200(7) 0.0025(6) 0.0069(6) 0.0056(6) OW4 0.0285(6) 0.0513(8) 0.0463(8) -0.0052(6) 0.0044(5) 0.0211(6) OW3 0.0322(6) 0.0607(9) 0.0526(8) 0.0008(7) 0.0090(6) 0.0237(6) OW1 0.0403(9) 0.1297(18) 0.0589(11) -0.0004(11) 0.0018(8) 0.0212(10) OW2 0.0407(8) 0.0780(11) 0.0544(9) 0.0100(8) 0.0017(7) 0.0231(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O2 1.5140(12) . ? P1 O3 1.5306(11) . ? P1 O5 1.5776(12) . ? P1 O4 1.5255(11) . ? P6 O8 1.5588(12) . ? P6 O10 1.4999(12) . ? P6 O7 1.5775(12) . ? P6 O9 1.5066(12) . ? P11 O12 1.5680(12) . ? P11 O14 1.5058(12) . ? P11 O15 1.5562(12) . ? P11 O13 1.5123(11) . ? N8B C7B 1.384(2) . ? N8B C9B 1.334(2) . ? N23B C15B 1.329(2) . ? N23B C22B 1.390(2) . ? N23A C22A 1.385(2) . ? N23A C15A 1.334(2) . ? C7B C2B 1.393(2) . ? C7B C6B 1.389(2) . ? C21A C22A 1.389(2) . ? C21A C20A 1.381(3) . ? C2A N1A 1.387(2) . ? C2A C7A 1.396(2) . ? C2A C3A 1.390(2) . ? N1A C9A 1.329(2) . ? C20B C19B 1.402(3) . ? C20B C21B 1.384(2) . ? C10B C11B 1.520(2) . ? C10B C9B 1.486(2) . ? C6A C7A 1.396(2) . ? C6A C5A 1.384(2) . ? N16A C17A 1.386(2) . ? N16A C15A 1.332(2) . ? C13A C14A 1.517(2) . ? C13A C12A 1.521(2) . ? N8A C7A 1.388(2) . ? N8A C9A 1.332(2) . ? C18B C19B 1.378(3) . ? C18B C17B 1.389(2) . ? C17A C22A 1.393(2) . ? C17A C18A 1.388(2) . ? C3B C2B 1.385(2) . ? C3B C4B 1.378(3) . ? C3A C4A 1.377(2) . ? C14A C15A 1.488(2) . ? N16B C15B 1.329(2) . ? N16B C17B 1.386(2) . ? C13B C14B 1.526(2) . ? C13B C12B 1.521(2) . ? C2B N1B 1.388(2) . ? C6B C5B 1.384(3) . ? N1B C9B 1.332(2) . ? C4B C5B 1.397(3) . ? C11A C10A 1.514(2) . ? C11A C12A 1.519(2) . ? C4A C5A 1.401(3) . ? C20A C19A 1.395(3) . ? C11B C12B 1.522(2) . ? C21B C22B 1.393(2) . ? C10A C9A 1.491(2) . ? C14B C15B 1.491(2) . ? C19A C18A 1.377(3) . ? C17B C22B 1.397(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 P1 O3 112.35(7) . . ? O2 P1 O5 108.64(6) . . ? O2 P1 O4 111.76(7) . . ? O3 P1 O5 106.31(7) . . ? O4 P1 O3 110.32(6) . . ? O4 P1 O5 107.17(8) . . ? O8 P6 O7 106.01(8) . . ? O10 P6 O8 108.76(7) . . ? O10 P6 O7 109.59(7) . . ? O10 P6 O9 116.40(8) . . ? O9 P6 O8 110.53(6) . . ? O9 P6 O7 105.02(7) . . ? O14 P11 O12 108.63(7) . . ? O14 P11 O15 111.15(8) . . ? O14 P11 O13 114.37(7) . . ? O15 P11 O12 108.00(7) . . ? O13 P11 O12 107.94(7) . . ? O13 P11 O15 106.54(6) . . ? C9B N8B C7B 108.90(13) . . ? C15B N23B C22B 109.08(13) . . ? C15A N23A C22A 108.65(13) . . ? N8B C7B C2B 106.37(14) . . ? N8B C7B C6B 132.06(15) . . ? C6B C7B C2B 121.58(16) . . ? C20A C21A C22A 116.55(17) . . ? N1A C2A C7A 106.48(13) . . ? N1A C2A C3A 131.18(14) . . ? C3A C2A C7A 122.34(14) . . ? C9A N1A C2A 108.80(13) . . ? C21B C20B C19B 121.92(16) . . ? C9B C10B C11B 114.06(14) . . ? C5A C6A C7A 116.35(15) . . ? C15A N16A C17A 108.71(13) . . ? C14A C13A C12A 113.80(14) . . ? C9A N8A C7A 108.84(13) . . ? C19B C18B C17B 116.51(15) . . ? C6A C7A C2A 121.08(15) . . ? N8A C7A C2A 106.18(13) . . ? N8A C7A C6A 132.73(15) . . ? N16A C17A C22A 106.44(14) . . ? N16A C17A C18A 131.80(16) . . ? C18A C17A C22A 121.76(16) . . ? C4B C3B C2B 116.60(16) . . ? C4A C3A C2A 116.39(15) . . ? C18B C19B C20B 121.63(16) . . ? N23A C22A C21A 131.87(16) . . ? N23A C22A C17A 106.53(14) . . ? C21A C22A C17A 121.59(16) . . ? C15A C14A C13A 113.70(13) . . ? C15B N16B C17B 109.48(13) . . ? C12B C13B C14B 114.40(14) . . ? C3B C2B C7B 121.87(16) . . ? C3B C2B N1B 131.59(15) . . ? N1B C2B C7B 106.53(14) . . ? C5B C6B C7B 116.37(16) . . ? C9B N1B C2B 108.62(13) . . ? C3B C4B C5B 121.77(17) . . ? C10A C11A C12A 114.66(14) . . ? C3A C4A C5A 121.65(16) . . ? C21A C20A C19A 121.54(18) . . ? C10B C11B C12B 113.19(14) . . ? C20B C21B C22B 116.69(15) . . ? C9A C10A C11A 112.76(13) . . ? C15B C14B C13B 111.92(13) . . ? C18A C19A C20A 122.20(18) . . ? C6A C5A C4A 122.18(16) . . ? C13B C12B C11B 109.81(14) . . ? N8B C9B C10B 123.73(14) . . ? N1B C9B N8B 109.58(14) . . ? N1B C9B C10B 126.68(14) . . ? C11A C12A C13A 110.22(13) . . ? C6B C5B C4B 121.81(17) . . ? N1A C9A N8A 109.70(14) . . ? N1A C9A C10A 125.46(14) . . ? N8A C9A C10A 124.83(14) . . ? C19A C18A C17A 116.36(18) . . ? N23B C15B N16B 109.24(14) . . ? N23B C15B C14B 125.78(14) . . ? N16B C15B C14B 124.97(14) . . ? N23A C15A C14A 124.23(14) . . ? N16A C15A N23A 109.65(14) . . ? N16A C15A C14A 126.11(14) . . ? C18B C17B C22B 122.31(15) . . ? N16B C17B C18B 131.75(15) . . ? N16B C17B C22B 105.93(14) . . ? N23B C22B C21B 132.79(14) . . ? N23B C22B C17B 106.26(13) . . ? C21B C22B C17B 120.94(15) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O8 H8 O2 0.84 1.67 2.4867(16) 164.4 1_655 O12 H12 O3 0.84 1.72 2.5502(16) 170.2 1_665 O15 H15 O4 0.84 1.67 2.5118(16) 174.4 1_665 O5 H5 O9 0.84 1.72 2.5483(16) 166.9 1_455 O7 H7 O13 0.84 1.70 2.5316(16) 168.0 . N8B H8B O13 0.88 1.77 2.6451(17) 171.5 1_455 N23B H23B O3 0.88 1.84 2.6916(17) 163.8 2_667 N23A H23A O14 0.88 1.73 2.6000(17) 168.8 1_545 N1A H1A O4 0.88 1.82 2.6587(17) 159.0 . N16A H16A OW3 0.88 1.86 2.7048(18) 160.4 . N8A H8A O10 0.88 1.80 2.6662(17) 167.4 2_666 N16B H16B O7 0.88 1.92 2.7670(17) 161.3 . N1B H1B OW4 0.88 1.83 2.6641(17) 158.7 . OW4 HW4A O14 0.87 1.86 2.7127(19) 168.0 . OW4 HW4B O10 0.87 1.86 2.7314(17) 177.9 . OW3 HW3A O3 0.87 2.06 2.8804(18) 157.9 . OW3 HW3B OW2 0.87 1.97 2.795(2) 158.6 . OW1 HW1A O9 0.86 1.88 2.693(2) 157.1 . OW2 HW2A O2 0.85 1.96 2.7363(19) 152.6 . OW2 HW2B OW1 0.85 2.09 2.832(3) 144.6 . loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -2 1 0 0.0334 -1.9996 1.0068 -0.0020 -0.2307 0.2050 0.0967 2 -1 0 0.0334 1.9996 -1.0068 0.0020 0.2307 -0.2050 -0.0967 0 1 0 0.0576 0.0012 1.0017 -0.0009 -0.0968 -0.0752 -0.0196 -1 -2 0 0.0995 -1.0027 -2.0010 0.0012 0.1267 0.2905 0.0975 0 1 -3 0.1268 -0.0006 1.0013 -2.9951 -0.0827 -0.0964 0.2337 -1 -1 3 0.1321 -0.9997 -0.9988 2.9945 0.0157 0.2365 -0.1756 #==END