#------------------------------------------------------------------------------ #$Date: 2015-12-31 12:29:25 +0000 (Thu, 31 Dec 2015) $ #$Revision: 171772 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/21/7112128.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7112128 loop_ _publ_author_name 'Tyler D. Boyd' 'Ish Kumar' 'Eric E. Wagner' 'Kenton H. Whitmire' _publ_section_title ; Synthesis and structural studies of the simplest bismuth(III) oxo-salicylate complex: [Bi4(mu3-O)2(HO-2-C6H4CO2)8].2Solv (Solv = MeCN or MeNO2) ; _journal_name_full Chem.Commun. _journal_page_first 3556 _journal_paper_doi 10.1039/C4CC00056K _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C56 H40 Bi4 O26, 2(C H3 N O2)' _chemical_formula_sum 'C58 H46 Bi4 N2 O30' _chemical_formula_weight 2086.89 _chemical_name_systematic ; tetrakis(salicylato)dioxotetrabismuthnitromethane solvate ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _cell_angle_alpha 68.7240(10) _cell_angle_beta 68.3960(10) _cell_angle_gamma 76.558(2) _cell_formula_units_Z 1 _cell_length_a 10.9483(11) _cell_length_b 11.5086(11) _cell_length_c 13.9101(14) _cell_measurement_temperature 273(2) _cell_volume 1508.6(3) _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.909 _diffrn_measurement_device_type BRUKERSMART1000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_unetI/netI 0.0534 _diffrn_reflns_laue_measured_fraction_full 0.998 _diffrn_reflns_laue_measured_fraction_max 0.909 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 19447 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.909 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.271 _diffrn_reflns_theta_min 1.911 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 11.727 _exptl_absorpt_correction_T_max 0.053 _exptl_absorpt_correction_T_min 0.042 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 5.1,1997' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.297 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 980 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _refine_diff_density_max 2.998 _refine_diff_density_min -2.235 _refine_diff_density_rms 0.204 _refine_ls_extinction_coef 0.00255(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 405 _refine_ls_number_reflns 7469 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.981 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0300 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0423P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.0778 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6381 _reflns_number_total 7469 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file c4cc00056k.cif _[local]_cod_data_source_block 1 _[local]_cod_chemical_formula_sum_orig 'C58 H46 Bi4 N2 O30 ' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 7112128 #BEGIN Tags that were not found in dictionaries: _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-2 _shelx_res_file ; TITL 1 in P-1 CELL 0.71073 10.9483 11.5086 13.9101 68.724 68.396 76.558 ZERR 2.00 0.0011 0.0011 0.0014 0.001 0.001 0.002 LATT 1 SFAC C H N O BI UNIT 58 46 2 30 4 TEMP 0.000 L.S. 30 BOND FMAP 2 PLAN 20 ACTA BOND $H OMIT 0 0 1 EQIV_$1 -x, -y+1, -z+1 MPLA 3 BI1 BI2 BI2_$1 O1 O1_$1 MPLA 4 BI1 BI2 BI1_$1 BI2_$1 O1 O1_$1 BIND Bi2 O12 WGHT 0.042300 EXTI 0.002549 FVAR 0.10092 BI1 5 0.299889 0.366315 0.516587 11.00000 0.00783 0.01078 = 0.01145 -0.00207 -0.00307 0.00052 BI2 5 0.050272 0.516960 0.358604 11.00000 0.00867 0.01344 = 0.01069 -0.00388 -0.00296 0.00045 O1 4 0.112680 0.435171 0.498368 11.00000 0.00839 0.01468 = 0.01100 -0.00399 -0.00438 0.00088 C111 1 0.396775 0.760114 0.254368 11.00000 0.01706 0.01568 = 0.00878 -0.00086 -0.00294 -0.00385 C112 1 0.343535 0.876853 0.197864 11.00000 0.01989 0.01736 = 0.02132 -0.00305 -0.00356 -0.00193 AFIX 43 H11A 2 0.255872 0.888016 0.199752 11.00000 -1.20000 AFIX 0 C113 1 0.418425 0.974254 0.140185 11.00000 0.03377 0.01847 = 0.02484 0.00040 -0.00928 -0.00342 AFIX 43 H11B 2 0.381178 1.051308 0.104024 11.00000 -1.20000 AFIX 0 C114 1 0.549699 0.958839 0.135269 11.00000 0.03205 0.02713 = 0.02240 0.00559 -0.00329 -0.01815 AFIX 43 H11C 2 0.600967 1.024888 0.094797 11.00000 -1.20000 AFIX 0 C115 1 0.603862 0.845661 0.190381 11.00000 0.02050 0.03699 = 0.02780 -0.00247 -0.00493 -0.01617 AFIX 43 H11D 2 0.691847 0.836293 0.187147 11.00000 -1.20000 AFIX 0 C116 1 0.530794 0.745624 0.250386 11.00000 0.01596 0.02283 = 0.01964 -0.00019 -0.00548 -0.00360 C117 1 0.315275 0.655585 0.314632 11.00000 0.01402 0.01757 = 0.01294 -0.00685 -0.00054 -0.00207 O111 4 0.198927 0.670084 0.313359 11.00000 0.01802 0.02084 = 0.02693 -0.00065 -0.01082 -0.00474 O112 4 0.369208 0.551619 0.366089 11.00000 0.01898 0.01307 = 0.02207 0.00173 -0.00578 -0.00365 O113 4 0.588257 0.636753 0.305049 11.00000 0.01650 0.03151 = 0.03220 0.00989 -0.01030 -0.00774 AFIX 143 H113 2 0.531072 0.591661 0.348697 11.00000 -1.50000 AFIX 0 C121 1 0.455421 0.314909 0.184911 11.00000 0.01566 0.01129 = 0.01508 -0.00499 0.00035 -0.00096 C122 1 0.583171 0.265130 0.190113 11.00000 0.01964 0.01936 = 0.02592 -0.01064 -0.00550 -0.00221 AFIX 43 H12A 2 0.600602 0.243975 0.255356 11.00000 -1.20000 AFIX 0 C123 1 0.684062 0.247055 0.098807 11.00000 0.00888 0.03622 = 0.03651 -0.01914 0.00371 0.00088 AFIX 43 H12B 2 0.769193 0.216193 0.102404 11.00000 -1.20000 AFIX 0 C124 1 0.657487 0.275119 0.002473 11.00000 0.02523 0.02997 = 0.02732 -0.01457 0.01146 -0.00665 AFIX 43 H12C 2 0.725069 0.261403 -0.058068 11.00000 -1.20000 AFIX 0 C125 1 0.533188 0.322837 -0.005367 11.00000 0.03732 0.03317 = 0.01344 -0.01161 0.00014 0.00341 AFIX 43 H12D 2 0.516986 0.341460 -0.070777 11.00000 -1.20000 AFIX 0 C126 1 0.430295 0.343470 0.086086 11.00000 0.02397 0.02197 = 0.01427 -0.00743 -0.00247 0.00509 C127 1 0.351227 0.341446 0.280622 11.00000 0.01090 0.01647 = 0.01354 -0.00520 -0.00250 -0.00030 O121 4 0.374571 0.298555 0.371369 11.00000 0.01879 0.01578 = 0.01790 -0.00678 -0.00454 0.00026 O122 4 0.243959 0.404660 0.268773 11.00000 0.01747 0.03255 = 0.01702 -0.01244 -0.00533 0.00663 O123 4 0.310964 0.388517 0.072209 11.00000 0.03159 0.06182 = 0.02694 -0.02339 -0.01192 0.01706 AFIX 143 H123 2 0.260681 0.409252 0.125275 11.00000 -1.50000 AFIX 0 C131 1 -0.215320 0.223870 0.484990 11.00000 0.01667 0.01337 = 0.01736 -0.00856 -0.00166 -0.00190 C132 1 -0.343427 0.228812 0.482688 11.00000 0.01603 0.01618 = 0.02204 -0.00979 -0.00280 -0.00035 C133 1 -0.407560 0.121084 0.530408 11.00000 0.01809 0.01983 = 0.04183 -0.01330 -0.00227 -0.00464 AFIX 43 H13A 2 -0.491382 0.123926 0.526767 11.00000 -1.20000 AFIX 0 C134 1 -0.346956 0.010952 0.582709 11.00000 0.02980 0.01760 = 0.02877 -0.00954 0.00527 -0.00885 AFIX 43 H13B 2 -0.390959 -0.060404 0.615344 11.00000 -1.20000 AFIX 0 C135 1 -0.220521 0.003479 0.588096 11.00000 0.03589 0.01122 = 0.02491 -0.00182 -0.00784 -0.00177 AFIX 43 H13C 2 -0.180759 -0.071836 0.624431 11.00000 -1.20000 AFIX 0 C136 1 -0.155192 0.109510 0.538708 11.00000 0.01666 0.01933 = 0.02441 -0.00451 -0.00862 0.00083 AFIX 43 H13D 2 -0.070393 0.105062 0.541081 11.00000 -1.20000 AFIX 0 C137 1 -0.144772 0.336948 0.432653 11.00000 0.01551 0.01602 = 0.01184 -0.00720 -0.00322 -0.00193 O131 4 -0.024647 0.324585 0.426502 11.00000 0.01287 0.01659 = 0.02773 -0.00805 -0.00766 -0.00081 O132 4 -0.205793 0.443794 0.393994 11.00000 0.01674 0.01103 = 0.02247 -0.00459 -0.01010 0.00133 O133 4 -0.408672 0.338786 0.433413 11.00000 0.01417 0.01649 = 0.04348 -0.00773 -0.01460 0.00384 AFIX 143 H133 2 -0.371865 0.398284 0.423951 11.00000 -1.50000 AFIX 0 C141 1 0.075099 0.061326 0.743518 11.00000 0.01708 0.01709 = 0.02124 0.00494 -0.00730 -0.00575 C142 1 0.093767 -0.039471 0.702301 11.00000 0.03905 0.01484 = 0.02800 0.00182 -0.01044 -0.01019 AFIX 43 H14A 2 0.154999 -0.038136 0.634652 11.00000 -1.20000 AFIX 0 C143 1 0.020797 -0.139960 0.762796 11.00000 0.05513 0.01818 = 0.03045 0.00128 -0.01962 -0.00687 AFIX 43 H14B 2 0.030642 -0.205151 0.735077 11.00000 -1.20000 AFIX 0 C144 1 -0.066509 -0.142905 0.864301 11.00000 0.03338 0.02683 = 0.03677 0.00536 -0.01529 -0.00729 AFIX 43 H14C 2 -0.114535 -0.211260 0.904651 11.00000 -1.20000 AFIX 0 C145 1 -0.084822 -0.048653 0.907611 11.00000 0.01922 0.04234 = 0.01583 0.00155 0.00055 -0.00592 AFIX 43 H14D 2 -0.144002 -0.053674 0.976679 11.00000 -1.20000 AFIX 0 C146 1 -0.013790 0.056359 0.847374 11.00000 0.02148 0.02830 = 0.01837 -0.00038 -0.00926 0.00087 C147 1 0.149101 0.170618 0.674819 11.00000 0.01436 0.01331 = 0.01674 0.00091 -0.00761 0.00058 O141 4 0.126806 0.268749 0.705091 11.00000 0.02025 0.01974 = 0.01424 -0.00406 -0.00493 -0.00079 O142 4 0.234162 0.168269 0.584215 11.00000 0.01906 0.01444 = 0.01897 -0.00386 0.00147 -0.00399 O143 4 -0.035535 0.146608 0.892407 11.00000 0.03267 0.03880 = 0.01953 -0.00419 0.00104 -0.00851 AFIX 143 H143 2 0.002524 0.206811 0.847489 11.00000 -1.50000 AFIX 0 O12 4 0.010767 0.455281 0.173284 11.00000 0.04300 N1 3 -0.071231 0.528699 0.134595 11.00000 0.03224 O11 4 -0.070504 0.640192 0.101971 11.00000 0.07818 C1 1 -0.180384 0.478742 0.130587 11.00000 0.04534 AFIX 33 H1A 2 -0.167361 0.388683 0.155370 11.00000 -1.50000 H1B 2 -0.182703 0.506931 0.057250 11.00000 -1.50000 H1C 2 -0.262493 0.507932 0.176518 11.00000 -1.50000 AFIX 0 HKLF 4 REM 1 in P-1 REM R1 = 0.0300 for 6381 Fo > 4sig(Fo) and 0.0385 for all 7469 data REM 405 parameters refined using 0 restraints END WGHT 0.0311 0.8290 REM Highest difference peak 2.998, deepest hole -2.235, 1-sigma level 0.204 Q1 1 0.3751 0.3590 0.5258 11.00000 0.05 3.00 Q2 1 -0.0222 0.5201 0.3479 11.00000 0.05 2.98 Q3 1 0.2222 0.3663 0.5105 11.00000 0.05 2.84 Q4 1 0.1205 0.5135 0.3707 11.00000 0.05 2.77 Q5 1 0.3062 0.4621 0.4722 11.00000 0.05 1.82 Q6 1 0.2925 0.2632 0.5699 11.00000 0.05 1.78 Q7 1 0.0572 0.6171 0.3067 11.00000 0.05 1.75 Q8 1 0.2598 0.4009 0.5798 11.00000 0.05 1.74 Q9 1 0.3442 0.3214 0.4561 11.00000 0.05 1.67 Q10 1 0.0076 0.5591 0.4177 11.00000 0.05 1.53 Q11 1 0.0375 0.4193 0.4102 11.00000 0.05 1.48 Q12 1 0.3156 0.3336 0.5966 11.00000 0.05 1.39 Q13 1 0.0816 0.4732 0.2997 11.00000 0.05 1.38 Q14 1 0.0960 0.4559 0.4402 11.00000 0.05 1.29 Q15 1 0.0233 0.5593 0.2791 11.00000 0.05 1.25 Q16 1 -0.0044 0.6255 0.0750 11.00000 0.05 1.11 Q17 1 0.2987 0.3729 0.4328 11.00000 0.05 1.07 Q18 1 0.0926 0.5761 0.3800 11.00000 0.05 1.02 Q19 1 -0.1184 0.6582 0.1117 11.00000 0.05 1.02 Q20 1 0.2749 0.2788 0.5141 11.00000 0.05 1.02 ; _shelx_res_checksum 55645 #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp Bi1 Bi 0.29989(2) 0.36632(2) 0.51659(2) 0.01069(6) Uani 1 1 d . . Bi2 Bi 0.05027(2) 0.51696(2) 0.35860(2) 0.01121(6) Uani 1 1 d . . O1 O 0.1127(3) 0.4352(3) 0.4984(2) 0.0113(6) Uani 1 1 d . . C111 C 0.3968(4) 0.7601(4) 0.2544(3) 0.0147(9) Uani 1 1 d . . C112 C 0.3435(5) 0.8769(5) 0.1979(4) 0.0213(10) Uani 1 1 d . . H11A H 0.2559 0.8880 0.1998 0.026 Uiso 1 1 calc R U C113 C 0.4184(5) 0.9743(5) 0.1402(4) 0.0277(11) Uani 1 1 d . . H11B H 0.3812 1.0513 0.1040 0.033 Uiso 1 1 calc R U C114 C 0.5497(5) 0.9588(5) 0.1353(4) 0.0300(12) Uani 1 1 d . . H11C H 0.6010 1.0249 0.0948 0.036 Uiso 1 1 calc R U C115 C 0.6039(5) 0.8457(5) 0.1904(4) 0.0291(12) Uani 1 1 d . . H11D H 0.6918 0.8363 0.1871 0.035 Uiso 1 1 calc R U C116 C 0.5308(4) 0.7456(5) 0.2504(4) 0.0211(10) Uani 1 1 d . . C117 C 0.3153(4) 0.6556(4) 0.3146(4) 0.0153(9) Uani 1 1 d . . O111 O 0.1989(3) 0.6701(3) 0.3134(3) 0.0223(7) Uani 1 1 d . . O112 O 0.3692(3) 0.5516(3) 0.3661(3) 0.0200(7) Uani 1 1 d . . O113 O 0.5883(3) 0.6368(4) 0.3050(3) 0.0308(9) Uani 1 1 d . . H113 H 0.5311 0.5917 0.3487 0.046 Uiso 1 1 calc R U C121 C 0.4554(4) 0.3149(4) 0.1849(4) 0.0154(9) Uani 1 1 d . . C122 C 0.5832(5) 0.2651(5) 0.1901(4) 0.0210(10) Uani 1 1 d . . H12A H 0.6006 0.2440 0.2554 0.025 Uiso 1 1 calc R U C123 C 0.6841(5) 0.2471(5) 0.0988(5) 0.0287(12) Uani 1 1 d . . H12B H 0.7692 0.2162 0.1024 0.034 Uiso 1 1 calc R U C124 C 0.6575(5) 0.2751(5) 0.0025(5) 0.0311(13) Uani 1 1 d . . H12C H 0.7251 0.2614 -0.0581 0.037 Uiso 1 1 calc R U C125 C 0.5332(5) 0.3228(5) -0.0054(4) 0.0304(12) Uani 1 1 d . . H12D H 0.5170 0.3415 -0.0708 0.037 Uiso 1 1 calc R U C126 C 0.4303(5) 0.3435(5) 0.0861(4) 0.0220(10) Uani 1 1 d . . C127 C 0.3512(4) 0.3414(4) 0.2806(4) 0.0141(9) Uani 1 1 d . . O121 O 0.3746(3) 0.2986(3) 0.3714(3) 0.0178(7) Uani 1 1 d . . O122 O 0.2440(3) 0.4047(3) 0.2688(3) 0.0227(8) Uani 1 1 d . . O123 O 0.3110(4) 0.3885(4) 0.0722(3) 0.0405(11) Uani 1 1 d . . H123 H 0.2607 0.4093 0.1253 0.061 Uiso 1 1 calc R U C131 C -0.2153(4) 0.2239(4) 0.4850(4) 0.0157(9) Uani 1 1 d . . C132 C -0.3434(4) 0.2288(4) 0.4827(4) 0.0181(9) Uani 1 1 d . . C133 C -0.4076(5) 0.1211(5) 0.5304(5) 0.0271(12) Uani 1 1 d . . H13A H -0.4914 0.1239 0.5268 0.033 Uiso 1 1 calc R U C134 C -0.3470(5) 0.0110(5) 0.5827(4) 0.0279(12) Uani 1 1 d . . H13B H -0.3910 -0.0604 0.6153 0.033 Uiso 1 1 calc R U C135 C -0.2205(5) 0.0035(5) 0.5881(4) 0.0258(11) Uani 1 1 d . . H13C H -0.1808 -0.0718 0.6244 0.031 Uiso 1 1 calc R U C136 C -0.1552(5) 0.1095(5) 0.5387(4) 0.0206(10) Uani 1 1 d . . H13D H -0.0704 0.1051 0.5411 0.025 Uiso 1 1 calc R U C137 C -0.1448(4) 0.3369(4) 0.4327(3) 0.0139(9) Uani 1 1 d . . O131 O -0.0246(3) 0.3246(3) 0.4265(3) 0.0185(7) Uani 1 1 d . . O132 O -0.2058(3) 0.4438(3) 0.3940(3) 0.0162(6) Uani 1 1 d . . O133 O -0.4087(3) 0.3388(3) 0.4334(3) 0.0245(8) Uani 1 1 d . . H133 H -0.3719 0.3983 0.4240 0.037 Uiso 1 1 calc R U C141 C 0.0751(4) 0.0613(4) 0.7435(4) 0.0206(10) Uani 1 1 d . . C142 C 0.0938(6) -0.0395(5) 0.7023(5) 0.0285(12) Uani 1 1 d . . H14A H 0.1550 -0.0381 0.6347 0.034 Uiso 1 1 calc R U C143 C 0.0208(6) -0.1400(5) 0.7628(5) 0.0348(14) Uani 1 1 d . . H14B H 0.0306 -0.2052 0.7351 0.042 Uiso 1 1 calc R U C144 C -0.0665(6) -0.1429(5) 0.8643(5) 0.0348(13) Uani 1 1 d . . H14C H -0.1145 -0.2113 0.9047 0.042 Uiso 1 1 calc R U C145 C -0.0848(5) -0.0487(5) 0.9076(4) 0.0303(12) Uani 1 1 d . . H14D H -0.1440 -0.0537 0.9767 0.036 Uiso 1 1 calc R U C146 C -0.0138(5) 0.0564(5) 0.8474(4) 0.0245(11) Uani 1 1 d . . C147 C 0.1491(4) 0.1706(4) 0.6748(4) 0.0160(9) Uani 1 1 d . . O141 O 0.1268(3) 0.2687(3) 0.7051(3) 0.0188(7) Uani 1 1 d . . O142 O 0.2342(3) 0.1683(3) 0.5842(3) 0.0197(7) Uani 1 1 d . . O143 O -0.0355(4) 0.1466(4) 0.8924(3) 0.0337(9) Uani 1 1 d . . H143 H 0.0025 0.2068 0.8475 0.051 Uiso 1 1 calc R U O12 O 0.0108(4) 0.4553(4) 0.1733(4) 0.0430(10) Uiso 1 1 d . . N1 N -0.0712(5) 0.5287(5) 0.1346(4) 0.0322(11) Uiso 1 1 d . . O11 O -0.0705(6) 0.6402(6) 0.1020(5) 0.0782(17) Uiso 1 1 d . . C1 C -0.1804(6) 0.4787(6) 0.1306(6) 0.0453(16) Uiso 1 1 d . . H1A H -0.1674 0.3887 0.1554 0.068 Uiso 1 1 calc R U H1B H -0.1827 0.5069 0.0573 0.068 Uiso 1 1 calc R U H1C H -0.2625 0.5079 0.1765 0.068 Uiso 1 1 calc R U 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 Bi1 0.00783(9) 0.01078(10) 0.01145(9) -0.00207(7) -0.00307(6) 0.00052(6) Bi2 0.00867(9) 0.01344(10) 0.01069(9) -0.00388(7) -0.00296(6) 0.00045(6) O1 0.0084(13) 0.0147(15) 0.0110(15) -0.0040(12) -0.0044(11) 0.0009(11) C111 0.017(2) 0.016(2) 0.009(2) -0.0009(18) -0.0029(16) -0.0038(17) C112 0.020(2) 0.017(2) 0.021(3) -0.003(2) -0.004(2) -0.0019(19) C113 0.034(3) 0.018(3) 0.025(3) 0.000(2) -0.009(2) -0.003(2) C114 0.032(3) 0.027(3) 0.022(3) 0.006(2) -0.003(2) -0.018(2) C115 0.020(2) 0.037(3) 0.028(3) -0.002(3) -0.005(2) -0.016(2) C116 0.016(2) 0.023(3) 0.020(2) 0.000(2) -0.0055(19) -0.0036(19) C117 0.014(2) 0.018(2) 0.013(2) -0.0068(19) -0.0005(17) -0.0021(18) O111 0.0180(16) 0.0208(18) 0.0269(19) -0.0006(15) -0.0108(14) -0.0047(14) O112 0.0190(16) 0.0131(17) 0.0221(18) 0.0017(14) -0.0058(14) -0.0037(13) O113 0.0165(17) 0.032(2) 0.032(2) 0.0099(17) -0.0103(16) -0.0077(15) C121 0.016(2) 0.011(2) 0.015(2) -0.0050(18) 0.0003(17) -0.0010(17) C122 0.020(2) 0.019(3) 0.026(3) -0.011(2) -0.006(2) -0.0022(19) C123 0.009(2) 0.036(3) 0.037(3) -0.019(3) 0.004(2) 0.001(2) C124 0.025(3) 0.030(3) 0.027(3) -0.015(3) 0.011(2) -0.007(2) C125 0.037(3) 0.033(3) 0.013(2) -0.012(2) 0.000(2) 0.003(2) C126 0.024(2) 0.022(3) 0.014(2) -0.007(2) -0.0025(19) 0.005(2) C127 0.0109(19) 0.016(2) 0.014(2) -0.0052(19) -0.0025(17) -0.0003(17) O121 0.0188(16) 0.0158(17) 0.0179(17) -0.0068(14) -0.0045(13) 0.0003(13) O122 0.0175(16) 0.033(2) 0.0170(17) -0.0124(16) -0.0053(14) 0.0066(15) O123 0.032(2) 0.062(3) 0.027(2) -0.023(2) -0.0119(18) 0.017(2) C131 0.017(2) 0.013(2) 0.017(2) -0.0086(19) -0.0017(17) -0.0019(17) C132 0.016(2) 0.016(2) 0.022(2) -0.010(2) -0.0028(18) -0.0004(18) C133 0.018(2) 0.020(3) 0.042(3) -0.013(2) -0.002(2) -0.005(2) C134 0.030(3) 0.018(3) 0.029(3) -0.010(2) 0.005(2) -0.009(2) C135 0.036(3) 0.011(2) 0.025(3) -0.002(2) -0.008(2) -0.002(2) C136 0.017(2) 0.019(3) 0.024(3) -0.005(2) -0.009(2) 0.0008(19) C137 0.016(2) 0.016(2) 0.012(2) -0.0072(18) -0.0032(17) -0.0019(17) O131 0.0129(15) 0.0166(17) 0.0277(19) -0.0081(15) -0.0077(14) -0.0008(13) O132 0.0167(15) 0.0110(16) 0.0225(17) -0.0046(14) -0.0101(13) 0.0013(12) O133 0.0142(16) 0.0165(18) 0.043(2) -0.0077(16) -0.0146(16) 0.0038(13) C141 0.017(2) 0.017(2) 0.021(2) 0.005(2) -0.0073(19) -0.0058(19) C142 0.039(3) 0.015(3) 0.028(3) 0.002(2) -0.010(2) -0.010(2) C143 0.055(4) 0.018(3) 0.030(3) 0.001(2) -0.020(3) -0.007(3) C144 0.033(3) 0.027(3) 0.037(3) 0.005(3) -0.015(3) -0.007(2) C145 0.019(2) 0.042(3) 0.016(3) 0.002(2) 0.001(2) -0.006(2) C146 0.021(2) 0.028(3) 0.018(2) 0.000(2) -0.009(2) 0.001(2) C147 0.014(2) 0.013(2) 0.017(2) 0.0009(18) -0.0076(18) 0.0006(17) O141 0.0202(16) 0.0197(18) 0.0142(16) -0.0041(14) -0.0049(13) -0.0008(13) O142 0.0191(16) 0.0144(17) 0.0190(17) -0.0039(14) 0.0015(13) -0.0040(13) O143 0.033(2) 0.039(2) 0.020(2) -0.0042(18) 0.0010(16) -0.0085(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1 Bi1 O121 93.94(11) . . O1 Bi1 O142 87.37(11) . . O121 Bi1 O142 76.41(12) . . O1 Bi1 O112 84.33(11) . . O121 Bi1 O112 76.20(12) . . O142 Bi1 O112 150.70(11) . . O1 Bi1 O141 73.41(10) . . O121 Bi1 O141 127.30(11) . . O142 Bi1 O141 52.63(10) . . O112 Bi1 O141 147.81(10) . . O1 Bi1 O132 73.51(10) . 2_566 O121 Bi1 O132 150.39(11) . 2_566 O142 Bi1 O132 128.11(10) . 2_566 O112 Bi1 O132 75.95(10) . 2_566 O141 Bi1 O132 75.60(10) . 2_566 O1 Bi1 C147 78.93(12) . . O121 Bi1 C147 101.34(12) . . O142 Bi1 C147 25.84(12) . . O112 Bi1 C147 162.90(11) . . O141 Bi1 C147 26.79(11) . . O132 Bi1 C147 102.30(11) 2_566 . O1 Bi2 O1 71.33(12) . 2_566 O1 Bi2 O131 78.64(11) . . O1 Bi2 O131 86.63(11) 2_566 . O1 Bi2 O122 86.76(11) . . O1 Bi2 O122 156.91(11) 2_566 . O131 Bi2 O122 81.84(12) . . O1 Bi2 O111 83.11(11) . . O1 Bi2 O111 99.94(11) 2_566 . O131 Bi2 O111 157.49(11) . . O122 Bi2 O111 84.10(12) . . O1 Bi2 O12 142.83(12) . . O1 Bi2 O12 126.14(11) 2_566 . O131 Bi2 O12 71.03(12) . . O122 Bi2 O12 68.42(11) . . O111 Bi2 O12 119.41(12) . . O1 Bi2 Bi2 37.13(8) . 2_566 O1 Bi2 Bi2 34.20(7) 2_566 2_566 O131 Bi2 Bi2 81.12(8) . 2_566 O122 Bi2 Bi2 123.54(8) . 2_566 O111 Bi2 Bi2 92.22(8) . 2_566 O12 Bi2 Bi2 148.05(8) . 2_566 Bi1 O1 Bi2 131.77(14) . . Bi1 O1 Bi2 117.34(12) . 2_566 Bi2 O1 Bi2 108.67(12) . 2_566 C112 C111 C116 118.4(4) . . C112 C111 C117 120.3(4) . . C116 C111 C117 121.3(4) . . C113 C112 C111 121.0(5) . . C113 C112 H11A 119.5 . . C111 C112 H11A 119.5 . . C112 C113 C114 120.3(5) . . C112 C113 H11B 119.9 . . C114 C113 H11B 119.9 . . C115 C114 C113 119.8(5) . . C115 C114 H11C 120.1 . . C113 C114 H11C 120.1 . . C114 C115 C116 121.5(5) . . C114 C115 H11D 119.2 . . C116 C115 H11D 119.2 . . O113 C116 C115 119.2(4) . . O113 C116 C111 121.8(4) . . C115 C116 C111 119.0(5) . . O111 C117 O112 123.0(4) . . O111 C117 C111 119.8(4) . . O112 C117 C111 117.3(4) . . C117 O111 Bi2 130.8(3) . . C117 O112 Bi1 138.0(3) . . C116 O113 H113 109.5 . . C122 C121 C126 118.8(4) . . C122 C121 C127 120.1(4) . . C126 C121 C127 121.1(4) . . C123 C122 C121 120.6(5) . . C123 C122 H12A 119.7 . . C121 C122 H12A 119.7 . . C124 C123 C122 119.8(5) . . C124 C123 H12B 120.1 . . C122 C123 H12B 120.1 . . C125 C124 C123 121.2(5) . . C125 C124 H12C 119.4 . . C123 C124 H12C 119.4 . . C124 C125 C126 119.7(5) . . C124 C125 H12D 120.1 . . C126 C125 H12D 120.1 . . O123 C126 C121 124.1(4) . . O123 C126 C125 116.0(5) . . C121 C126 C125 119.9(4) . . O122 C127 O121 123.4(4) . . O122 C127 C121 118.6(4) . . O121 C127 C121 118.0(4) . . C127 O121 Bi1 131.8(3) . . C127 O122 Bi2 141.5(3) . . C126 O123 H123 109.5 . . C132 C131 C136 118.8(4) . . C132 C131 C137 120.9(4) . . C136 C131 C137 120.4(4) . . O133 C132 C133 118.3(4) . . O133 C132 C131 121.5(4) . . C133 C132 C131 120.2(5) . . C134 C133 C132 119.8(5) . . C134 C133 H13A 120.1 . . C132 C133 H13A 120.1 . . C133 C134 C135 121.4(5) . . C133 C134 H13B 119.3 . . C135 C134 H13B 119.3 . . C136 C135 C134 119.1(5) . . C136 C135 H13C 120.5 . . C134 C135 H13C 120.5 . . C135 C136 C131 120.8(5) . . C135 C136 H13D 119.6 . . C131 C136 H13D 119.6 . . O131 C137 O132 122.0(4) . . O131 C137 C131 118.3(4) . . O132 C137 C131 119.7(4) . . C137 O131 Bi2 110.1(3) . . C137 O132 Bi1 127.0(3) . 2_566 C132 O133 H133 109.5 . . C146 C141 C142 119.7(5) . . C146 C141 C147 121.5(4) . . C142 C141 C147 118.8(5) . . C143 C142 C141 119.9(5) . . C143 C142 H14A 120.1 . . C141 C142 H14A 120.1 . . C144 C143 C142 119.6(6) . . C144 C143 H14B 120.2 . . C142 C143 H14B 120.2 . . C145 C144 C143 122.1(5) . . C145 C144 H14C 119.0 . . C143 C144 H14C 119.0 . . C144 C145 C146 119.9(5) . . C144 C145 H14D 120.1 . . C146 C145 H14D 120.1 . . O143 C146 C141 123.3(5) . . O143 C146 C145 117.8(5) . . C141 C146 C145 118.9(5) . . O142 C147 O141 119.6(4) . . O142 C147 C141 119.5(4) . . O141 C147 C141 120.8(4) . . O142 C147 Bi1 52.4(2) . . O141 C147 Bi1 67.2(2) . . C141 C147 Bi1 171.4(3) . . C147 O141 Bi1 86.0(3) . . C147 O142 Bi1 101.7(3) . . C146 O143 H143 109.5 . . N1 O12 Bi2 113.8(3) . . O11 N1 O12 124.0(5) . . O11 N1 C1 117.5(5) . . O12 N1 C1 118.5(5) . . N1 C1 H1A 109.5 . . N1 C1 H1B 109.5 . . H1A C1 H1B 109.5 . . N1 C1 H1C 109.5 . . H1A C1 H1C 109.5 . . H1B C1 H1C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Bi1 O1 2.092(3) . Bi1 O121 2.233(3) . Bi1 O142 2.303(3) . Bi1 O112 2.418(3) . Bi1 O141 2.631(3) . Bi1 O132 2.714(3) 2_566 Bi1 C147 2.846(5) . Bi2 O1 2.117(3) . Bi2 O1 2.274(3) 2_566 Bi2 O131 2.285(3) . Bi2 O122 2.382(3) . Bi2 O111 2.434(3) . Bi2 O12 3.103(4) . Bi2 Bi2 3.5686(5) 2_566 O1 Bi2 2.274(3) 2_566 C111 C112 1.403(6) . C111 C116 1.420(6) . C111 C117 1.471(6) . C112 C113 1.365(7) . C112 H11A 0.9300 . C113 C114 1.386(7) . C113 H11B 0.9300 . C114 C115 1.374(8) . C114 H11C 0.9300 . C115 C116 1.379(7) . C115 H11D 0.9300 . C116 O113 1.356(6) . C117 O111 1.252(5) . C117 O112 1.286(5) . O113 H113 0.8200 . C121 C122 1.401(6) . C121 C126 1.408(6) . C121 C127 1.477(6) . C122 C123 1.389(7) . C122 H12A 0.9300 . C123 C124 1.383(8) . C123 H12B 0.9300 . C124 C125 1.373(8) . C124 H12C 0.9300 . C125 C126 1.408(6) . C125 H12D 0.9300 . C126 O123 1.346(6) . C127 O122 1.263(5) . C127 O121 1.276(5) . O123 H123 0.8200 . C131 C132 1.402(6) . C131 C136 1.403(6) . C131 C137 1.478(6) . C132 O133 1.376(5) . C132 C133 1.391(7) . C133 C134 1.368(7) . C133 H13A 0.9300 . C134 C135 1.395(7) . C134 H13B 0.9300 . C135 C136 1.381(8) . C135 H13C 0.9300 . C136 H13D 0.9300 . C137 O131 1.263(5) . C137 O132 1.285(5) . O132 Bi1 2.714(3) 2_566 O133 H133 0.8200 . C141 C146 1.403(7) . C141 C142 1.415(7) . C141 C147 1.478(6) . C142 C143 1.383(8) . C142 H14A 0.9300 . C143 C144 1.377(8) . C143 H14B 0.9300 . C144 C145 1.365(8) . C144 H14C 0.9300 . C145 C146 1.411(7) . C145 H14D 0.9300 . C146 O143 1.332(6) . C147 O142 1.267(5) . C147 O141 1.286(5) . O143 H143 0.8200 . O12 N1 1.218(6) . N1 O11 1.197(7) . N1 C1 1.468(7) . C1 H1A 0.9600 . C1 H1B 0.9600 . C1 H1C 0.9600 .