# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2016 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 1429287' _audit_update_record ; 2015-10-28 deposited with the CCDC. 2016-02-12 downloaded from the CCDC. ; # start Validation Reply Form _vrf_PLAT213_1 ; PROBLEM: Atom C161 has ADP max/min Ratio ..... 4.3 oblate RESPONSE: Part of highly disordered HB(C6F5)3 counterion, which is modelled over 2 sites ; _vrf_PLAT413_1 ; PROBLEM: Short Inter XH3 .. XHn H2011 .. H2 .. 1.97 Ang. RESPONSE: H2 is the hydride of the disorder counterion, the minor component of which has a close HH distance ; # Added during the CSD deposition process: Wednesday 28th of October 2015 11:24:53 AM # end Validation Reply Form _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 10.3052(10) _cell_length_b 33.5364(19) _cell_length_c 10.5825(11) _cell_angle_alpha 90 _cell_angle_beta 117.953(13) _cell_angle_gamma 90 _cell_volume 3230.6(6) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,-y+1/2,z+1/2 -x+1/2,y+1/2,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 '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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C31 H27 B2 F15 N2 # Dc = 1.51 Fooo = 1536.01 Mu = 1.48 M = 734.16 # Found Formula = C33.00 H27 B2 F15.00 N2 # Dc = 1.56 FOOO = 1536.01 Mu = 1.51 M = 758.19 _chemical_formula_sum 'C33 H27 B2 F15 N2' _chemical_formula_moiety 'C18 H B F15, C15 H26 B N2' _chemical_compound_source 'University of Manchester' _chemical_formula_weight 758.19 _cell_measurement_temperature 151(2) _cell_measurement_reflns_used 3322 _cell_measurement_theta_min 3.3310 _cell_measurement_theta_max 26.3520 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1536.008 _exptl_absorpt_coefficient_mu 0.151 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_T_min 0.41179 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 21.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -25.3942 57.0000 60.0000 75 #__ type_ start__ end____ width___ exp.time_ 2 omega -7.00 27.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -25.3942 -99.0000 30.0000 34 #__ type_ start__ end____ width___ exp.time_ 3 omega -68.00 49.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -25.3942 19.0000 -90.0000 117 #__ type_ start__ end____ width___ exp.time_ 4 omega 86.00 116.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - 25.8629 178.0000 30.0000 30 ; _diffrn_measurement_method '\w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrysAlisPro, Agilent Technologies (2013)' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies (2013)' _computing_data_reduction 'CrysAlisPro, Agilent Technologies (2013)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'Ortep3 v. 2.02 (LJ Farrugia, 1997)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 151(2) _diffrn_reflns_number 13188 _reflns_number_total 7156 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 7156 # Theoretical number of reflections is about 16405 _diffrn_reflns_theta_min 3.264 _diffrn_reflns_theta_max 28.516 _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 26.320 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -13 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 43 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 2.95 _oxford_diffrn_Wilson_scale 0.21 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.45 _refine_diff_density_max 0.56 # 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>0.0\s(I) _refine_ls_number_reflns 7143 _refine_ls_number_restraints 228 _refine_ls_number_parameters 771 _oxford_refine_ls_R_factor_ref 0.0985 _refine_ls_wR_factor_ref 0.1613 _refine_ls_goodness_of_fit_ref 1.0269 _refine_ls_shift/su_max 0.0005265 _refine_ls_shift/su_mean 0.0000389 # The values computed with all filters except I/sigma _oxford_reflns_number_all 7143 _refine_ls_R_factor_all 0.0985 _refine_ls_wR_factor_all 0.1613 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5196 _refine_ls_R_factor_gt 0.0717 _refine_ls_wR_factor_gt 0.1491 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 8.22P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F20 F 0.6900(3) 0.41377(8) 0.3796(3) 0.0425 0.811(3) Uani D U P . . . F21 F 0.7200(14) 0.4022(3) 0.3228(12) 0.0452 0.189(3) Uani D U P . . . F30 F 0.5765(4) 0.48574(11) 0.3745(4) 0.0514 0.811(3) Uani D U P . . . F31 F 0.6298(17) 0.4652(5) 0.4106(15) 0.0515 0.189(3) Uani D U P . . . F40 F 0.5748(4) 0.54272(10) 0.1936(5) 0.0546 0.811(3) Uani D U P . . . F41 F 0.602(2) 0.5362(5) 0.278(2) 0.0641 0.189(3) Uani D U P . . . F50 F 0.6967(3) 0.52682(9) 0.0185(4) 0.0518 0.811(3) Uani D U P . . . F51 F 0.6527(16) 0.5433(4) 0.0513(15) 0.0537 0.189(3) Uani D U P . . . F60 F 0.8182(3) 0.45665(8) 0.0274(3) 0.0429 0.811(3) Uani D U P . . . F61 F 0.7468(13) 0.4802(3) -0.0355(11) 0.0408 0.189(3) Uani D U P . . . F80 F 1.1070(4) 0.43593(10) 0.3737(4) 0.0544 0.811(3) Uani D U P . . . F81 F 1.0279(16) 0.4420(4) 0.3231(18) 0.0620 0.189(3) Uani D U P . . . F90 F 1.3366(5) 0.43953(16) 0.3237(5) 0.0710 0.811(3) Uani D U P . . . F91 F 1.308(2) 0.4464(7) 0.381(3) 0.0872 0.189(3) Uani D U P . . . F100 F 1.3448(4) 0.39489(12) 0.1124(5) 0.0627 0.811(3) Uani D U P . . . F101 F 1.3929(18) 0.4059(6) 0.205(3) 0.0894 0.189(3) Uani D U P . . . F110 F 1.1129(4) 0.34695(11) -0.0506(4) 0.0594 0.811(3) Uani D U P . . . F111 F 1.204(2) 0.3576(7) 0.002(2) 0.0902 0.189(3) Uani D U P . . . F120 F 0.8772(3) 0.34553(9) -0.0121(3) 0.0466 0.811(3) Uani D U P . . . F121 F 0.9234(16) 0.3523(5) -0.0561(14) 0.0591 0.189(3) Uani D U P . . . F140 F 0.9136(3) 0.30626(8) 0.3035(3) 0.0462 0.811(3) Uani D U P . . . F141 F 0.9333(13) 0.3276(4) 0.2543(14) 0.0540 0.189(3) Uani D U P . . . F150 F 0.7264(4) 0.24470(9) 0.2090(4) 0.0571 0.811(3) Uani D U P . . . F151 F 0.800(2) 0.2601(5) 0.262(2) 0.0847 0.189(3) Uani D U P . . . F160 F 0.4452(4) 0.25577(9) 0.0065(4) 0.0508 0.811(3) Uani D U P . . . F161 F 0.508(2) 0.2522(4) 0.106(2) 0.0773 0.189(3) Uani D U P . . . F170 F 0.3538(3) 0.32908(10) -0.1119(4) 0.0460 0.811(3) Uani D U P . . . F171 F 0.3481(19) 0.3141(6) -0.058(2) 0.0735 0.189(3) Uani D U P . . . F180 F 0.5378(4) 0.39082(8) -0.0192(3) 0.0407 0.811(3) Uani D U P . . . F181 F 0.4758(15) 0.3802(4) -0.0783(16) 0.0477 0.189(3) Uani D U P . . . C10 C 0.7657(6) 0.43183(14) 0.2072(7) 0.0268 0.811(3) Uani . U P . . . C11 C 0.734(2) 0.4388(7) 0.133(2) 0.0195 0.189(3) Uani . U P . . . C20 C 0.6976(8) 0.44166(19) 0.2893(7) 0.0288 0.811(3) Uani D U P . . . C21 C 0.708(4) 0.4359(6) 0.246(3) 0.0328 0.189(3) Uani D U P . . . C30 C 0.6375(14) 0.4785(3) 0.2893(10) 0.0331 0.811(3) Uani D U P . . . C31 C 0.649(6) 0.4666(11) 0.294(4) 0.0217 0.189(3) Uani D U P . . . C40 C 0.6367(11) 0.50729(18) 0.1976(8) 0.0327 0.811(3) Uani D U P . . . C41 C 0.640(5) 0.5017(9) 0.239(4) 0.0317 0.189(3) Uani D U P . . . C50 C 0.6980(8) 0.49898(19) 0.1107(8) 0.0326 0.811(3) Uani D U P . . . C51 C 0.664(4) 0.5080(8) 0.117(5) 0.0384 0.189(3) Uani D U P . . . C60 C 0.7591(5) 0.46228(19) 0.1161(5) 0.0284 0.811(3) Uani D U P . . . C61 C 0.710(3) 0.4769(9) 0.072(2) 0.0341 0.189(3) Uani D U P . . . C70 C 0.9801(5) 0.39042(15) 0.1857(6) 0.0307 0.811(3) Uani . U P . . . C71 C 0.959(2) 0.3989(7) 0.125(2) 0.0257 0.189(3) Uani . U P . . . C80 C 1.1024(9) 0.4136(3) 0.2656(6) 0.0386 0.811(3) Uani D U P . . . C81 C 1.065(5) 0.4219(11) 0.234(3) 0.0404 0.189(3) Uani D U P . . . C90 C 1.2226(12) 0.4164(4) 0.2399(12) 0.0452 0.811(3) Uani D U P . . . C91 C 1.217(6) 0.4218(18) 0.278(5) 0.0529 0.189(3) Uani D U P . . . C100 C 1.2252(7) 0.3932(2) 0.1335(10) 0.0428 0.811(3) Uani D U P . . . C101 C 1.249(2) 0.4042(13) 0.172(6) 0.0428 0.189(3) Uani D U P . . . C110 C 1.1080(9) 0.3698(2) 0.0515(8) 0.0410 0.811(3) Uani D U P . . . C111 C 1.155(4) 0.3782(11) 0.081(4) 0.0350 0.189(3) Uani D U P . . . C120 C 0.9902(8) 0.3690(2) 0.0775(6) 0.0348 0.811(3) Uani D U P . . . C121 C 1.011(4) 0.3783(8) 0.048(2) 0.0394 0.189(3) Uani D U P . . . C130 C 0.7329(5) 0.35217(16) 0.1551(6) 0.0268 0.811(3) Uani . U P . . . C131 C 0.707(3) 0.3570(6) 0.086(2) 0.0227 0.189(3) Uani . U P . . . C140 C 0.7740(5) 0.31340(19) 0.2044(6) 0.0303 0.811(3) Uani D U P . . . C141 C 0.7863(16) 0.3262(9) 0.171(2) 0.0337 0.189(3) Uani D U P . . . C150 C 0.6784(8) 0.28137(15) 0.1539(7) 0.0343 0.811(3) Uani D U P . . . C151 C 0.719(4) 0.2915(7) 0.182(3) 0.0299 0.189(3) Uani D U P . . . C160 C 0.5369(7) 0.28712(18) 0.0510(6) 0.0302 0.811(3) Uani D U P . . . C161 C 0.570(4) 0.2873(8) 0.102(3) 0.0291 0.189(3) Uani D U P . . . C170 C 0.4913(6) 0.3243(2) -0.0064(7) 0.0277 0.811(3) Uani D U P . . . C171 C 0.494(2) 0.3155(13) 0.027(3) 0.0273 0.189(3) Uani D U P . . . C180 C 0.5907(8) 0.35561(16) 0.0460(7) 0.0255 0.811(3) Uani D U P . . . C181 C 0.550(4) 0.3497(8) 0.010(4) 0.0376 0.189(3) Uani D U P . . . C200 C 0.7632(4) 0.36724(9) 0.6436(3) 0.0303 1.0000 Uani . . . . . . C201 C 0.6260(4) 0.42258(11) 0.6863(5) 0.0466 1.0000 Uani . . . . . . C202 C 0.8759(4) 0.42635(10) 0.7032(4) 0.0361 1.0000 Uani . . . . . . C203 C 0.8947(5) 0.46951(11) 0.7401(5) 0.0524 1.0000 Uani . . . . . . C204 C 0.9660(4) 0.40095(10) 0.6815(4) 0.0347 1.0000 Uani . . . . . . C205 C 1.1122(4) 0.40714(12) 0.6898(5) 0.0473 1.0000 Uani . . . . . . C206 C 0.9592(4) 0.32859(11) 0.6221(5) 0.0452 1.0000 Uani . . . . . . C208 C 0.6006(4) 0.30610(11) 0.4687(4) 0.0433 1.0000 Uani . . . . . . C209 C 0.4457(5) 0.32081(14) 0.3669(4) 0.0577 1.0000 Uani . . . . . . C210 C 0.3330(4) 0.31564(13) 0.4221(4) 0.0549 1.0000 Uani . . . . . . C211 C 0.3834(4) 0.33124(12) 0.5711(5) 0.0490 1.0000 Uani . . . . . . C212 C 0.5492(4) 0.32505(11) 0.6773(4) 0.0397 1.0000 Uani . . . . . . C213 C 0.5881(5) 0.28187(12) 0.7309(4) 0.0493 1.0000 Uani . . . . . . C214 C 0.5512(5) 0.25075(12) 0.6140(5) 0.0509 1.0000 Uani . . . . . . C215 C 0.6093(5) 0.26143(11) 0.5093(5) 0.0505 1.0000 Uani . . . . . . B10 B 0.8479(5) 0.38870(13) 0.2297(5) 0.0291 0.811(3) Uani . . P . . . B11 B 0.779(2) 0.3990(5) 0.0688(19) 0.0240 0.189(3) Uani . . P . . . B20 B 0.6438(4) 0.33350(11) 0.6003(4) 0.0318 1.0000 Uani . . . . . . N1 N 0.7536(3) 0.40516(8) 0.6816(3) 0.0320 1.0000 Uani . . . . . . N2 N 0.8937(3) 0.36495(8) 0.6449(3) 0.0320 1.0000 Uani . . . . . . H1 H 0.8955 0.3813 0.3491 0.0251 0.8108 Uiso R . . . . . H2 H 0.7403 0.4002 -0.0576 0.0448 0.1893 Uiso R . . . . . H2011 H 0.6545 0.4358 0.7751 0.0708 1.0000 Uiso R . . . . . H2012 H 0.5543 0.4029 0.6731 0.0698 1.0000 Uiso R . . . . . H2013 H 0.5830 0.4417 0.6119 0.0709 1.0000 Uiso R . . . . . H2031 H 0.8113 0.4846 0.6710 0.0782 1.0000 Uiso R . . . . . H2032 H 0.9021 0.4734 0.8330 0.0785 1.0000 Uiso R . . . . . H2033 H 0.9812 0.4791 0.7398 0.0779 1.0000 Uiso R . . . . . H2051 H 1.1141 0.3959 0.6079 0.0712 1.0000 Uiso R . . . . . H2052 H 1.1885 0.3947 0.7753 0.0709 1.0000 Uiso R . . . . . H2053 H 1.1295 0.4351 0.6904 0.0709 1.0000 Uiso R . . . . . H2061 H 1.0565 0.3247 0.7002 0.0671 1.0000 Uiso R . . . . . H2062 H 0.8991 0.3060 0.6144 0.0673 1.0000 Uiso R . . . . . H2063 H 0.9667 0.3315 0.5353 0.0666 1.0000 Uiso R . . . . . H2081 H 0.6637 0.3115 0.4229 0.0498 1.0000 Uiso R . . . . . H2091 H 0.4536 0.3495 0.3536 0.0681 1.0000 Uiso R . . . . . H2092 H 0.4105 0.3072 0.2757 0.0682 1.0000 Uiso R . . . . . H2101 H 0.2407 0.3290 0.3571 0.0654 1.0000 Uiso R . . . . . H2102 H 0.3118 0.2870 0.4208 0.0647 1.0000 Uiso R . . . . . H2111 H 0.3639 0.3597 0.5643 0.0582 1.0000 Uiso R . . . . . H2112 H 0.3271 0.3177 0.6114 0.0578 1.0000 Uiso R . . . . . H2121 H 0.5812 0.3424 0.7624 0.0462 1.0000 Uiso R . . . . . H2131 H 0.6953 0.2805 0.7964 0.0580 1.0000 Uiso R . . . . . H2132 H 0.5355 0.2751 0.7829 0.0583 1.0000 Uiso R . . . . . H2141 H 0.5919 0.2248 0.6580 0.0607 1.0000 Uiso R . . . . . H2142 H 0.4426 0.2486 0.5592 0.0614 1.0000 Uiso R . . . . . H2151 H 0.7103 0.2524 0.5494 0.0596 1.0000 Uiso R . . . . . H2152 H 0.5495 0.2472 0.4202 0.0603 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 F20 0.0492(16) 0.0392(16) 0.0490(17) 0.0103(13) 0.0313(14) -0.0001(12) F21 0.076(8) 0.036(6) 0.042(6) -0.003(5) 0.043(6) 0.001(5) F30 0.052(2) 0.051(2) 0.069(2) -0.0113(17) 0.0428(18) -0.0026(15) F31 0.064(9) 0.055(9) 0.054(7) -0.012(7) 0.043(7) -0.006(7) F40 0.0439(19) 0.0228(16) 0.096(3) 0.0006(19) 0.032(2) 0.0083(13) F41 0.057(8) 0.032(7) 0.097(12) 0.002(9) 0.030(9) 0.019(6) F50 0.0561(19) 0.0304(17) 0.066(2) 0.0205(15) 0.0266(16) 0.0042(14) F51 0.066(8) 0.024(6) 0.062(8) 0.009(6) 0.022(6) 0.015(6) F60 0.0585(17) 0.0401(16) 0.0387(14) 0.0083(12) 0.0300(13) 0.0065(13) F61 0.062(7) 0.026(6) 0.035(6) 0.005(5) 0.024(5) 0.004(5) F80 0.051(2) 0.0403(18) 0.069(2) -0.0156(17) 0.0252(19) -0.0166(17) F81 0.038(7) 0.032(7) 0.078(10) -0.027(6) -0.004(7) 0.000(6) F90 0.044(2) 0.063(3) 0.097(4) -0.005(2) 0.025(2) -0.0245(19) F91 0.053(10) 0.047(9) 0.113(15) -0.008(10) -0.001(9) -0.006(8) F100 0.049(2) 0.066(2) 0.094(3) 0.029(2) 0.051(2) 0.0092(18) F101 0.039(8) 0.089(12) 0.145(14) 0.029(12) 0.047(10) 0.001(8) F110 0.064(2) 0.075(2) 0.053(2) 0.0037(17) 0.0391(19) 0.0105(19) F111 0.063(9) 0.129(13) 0.086(11) 0.011(10) 0.041(9) 0.023(10) F120 0.0450(16) 0.0569(18) 0.0403(16) -0.0099(14) 0.0221(13) -0.0053(13) F121 0.066(8) 0.086(9) 0.042(7) 0.005(7) 0.039(6) 0.017(7) F140 0.0476(16) 0.0274(15) 0.0460(16) 0.0042(13) 0.0072(13) 0.0099(12) F141 0.052(7) 0.044(7) 0.064(8) 0.035(6) 0.027(6) 0.021(6) F150 0.084(3) 0.0178(15) 0.0512(19) 0.0071(13) 0.0163(18) 0.0023(14) F151 0.120(13) 0.049(9) 0.097(12) 0.026(9) 0.061(10) 0.013(9) F160 0.065(2) 0.0302(15) 0.0560(19) -0.0062(15) 0.0270(17) -0.0220(14) F161 0.111(11) 0.033(7) 0.109(11) -0.016(9) 0.069(10) -0.029(8) F170 0.0347(15) 0.039(2) 0.052(2) -0.0071(14) 0.0097(14) -0.0009(13) F171 0.060(8) 0.071(11) 0.092(12) -0.020(9) 0.037(9) -0.020(8) F180 0.0413(18) 0.0199(14) 0.0479(19) 0.0048(13) 0.0100(14) 0.0024(12) F181 0.034(7) 0.039(7) 0.062(9) -0.010(6) 0.015(6) 0.000(6) C10 0.031(3) 0.022(2) 0.029(3) -0.003(2) 0.015(2) -0.0044(18) C11 0.021(8) 0.023(10) 0.023(9) -0.003(8) 0.017(8) -0.005(7) C20 0.025(2) 0.029(3) 0.032(3) 0.002(3) 0.013(3) -0.004(2) C21 0.053(13) 0.014(10) 0.032(14) -0.005(9) 0.020(11) -0.012(9) C30 0.035(3) 0.021(6) 0.046(3) -0.009(3) 0.022(2) -0.006(4) C31 0.034(11) 0.009(17) 0.039(10) -0.010(10) 0.031(8) -0.008(12) C40 0.028(2) 0.021(2) 0.047(5) -0.002(2) 0.016(4) 0.000(2) C41 0.028(7) 0.027(9) 0.044(11) -0.010(8) 0.021(9) -0.003(8) C50 0.031(4) 0.020(3) 0.040(3) 0.009(3) 0.011(3) 0.000(3) C51 0.033(11) 0.025(9) 0.043(8) 0.003(9) 0.005(8) 0.009(8) C60 0.033(3) 0.022(3) 0.032(3) -0.002(2) 0.016(2) -0.004(2) C61 0.041(11) 0.019(11) 0.040(11) 0.014(9) 0.018(9) 0.016(9) C70 0.030(2) 0.029(3) 0.031(3) 0.008(2) 0.013(2) 0.0051(19) C71 0.023(8) 0.031(10) 0.025(10) 0.016(8) 0.013(8) -0.002(7) C80 0.038(5) 0.025(4) 0.051(3) 0.005(3) 0.019(3) 0.001(3) C81 0.036(15) 0.014(12) 0.066(13) 0.019(10) 0.019(11) 0.009(9) C90 0.036(3) 0.040(5) 0.055(6) 0.011(3) 0.017(4) -0.010(3) C91 0.045(13) 0.043(15) 0.057(19) 0.020(14) 0.013(14) 0.003(12) C100 0.037(4) 0.036(5) 0.065(7) 0.017(4) 0.031(4) 0.006(3) C101 0.031(8) 0.035(12) 0.067(12) 0.020(9) 0.028(8) -0.009(8) C110 0.036(5) 0.045(4) 0.039(4) 0.015(3) 0.016(3) 0.006(3) C111 0.021(14) 0.052(16) 0.039(13) -0.006(10) 0.020(12) 0.002(12) C120 0.033(3) 0.033(3) 0.036(3) 0.009(3) 0.014(2) 0.003(2) C121 0.038(13) 0.039(13) 0.033(11) 0.015(10) 0.010(10) 0.009(10) C130 0.033(2) 0.021(2) 0.030(3) 0.000(2) 0.018(2) 0.0030(19) C131 0.036(10) 0.015(8) 0.021(9) 0.002(8) 0.017(9) 0.002(7) C140 0.034(2) 0.022(4) 0.033(3) 0.000(2) 0.014(2) 0.000(2) C141 0.038(10) 0.026(13) 0.046(11) 0.012(9) 0.028(8) -0.009(9) C150 0.053(5) 0.014(3) 0.032(3) -0.003(2) 0.017(3) -0.002(2) C151 0.048(10) 0.014(9) 0.029(9) -0.002(8) 0.019(7) -0.001(8) C160 0.043(4) 0.021(2) 0.028(3) -0.005(2) 0.017(3) -0.010(2) C161 0.045(9) 0.016(7) 0.031(10) 0.001(8) 0.022(8) -0.018(7) C170 0.033(2) 0.023(4) 0.030(3) 0.001(2) 0.017(2) -0.002(2) C171 0.032(7) 0.022(10) 0.035(10) 0.002(8) 0.022(6) -0.012(6) C180 0.027(4) 0.016(2) 0.037(4) -0.001(2) 0.018(3) -0.005(2) C181 0.020(14) 0.038(13) 0.047(14) -0.010(11) 0.009(10) 0.007(11) C200 0.0340(17) 0.0228(16) 0.0357(17) -0.0009(14) 0.0177(14) 0.0011(13) C201 0.042(2) 0.034(2) 0.068(3) -0.0135(19) 0.030(2) -0.0011(16) C202 0.0352(18) 0.0299(18) 0.0388(19) -0.0047(15) 0.0139(15) -0.0060(14) C203 0.058(3) 0.032(2) 0.072(3) -0.015(2) 0.035(2) -0.0138(18) C204 0.0343(18) 0.0310(18) 0.0381(19) -0.0018(15) 0.0163(15) -0.0051(14) C205 0.038(2) 0.046(2) 0.060(3) -0.0017(19) 0.0245(19) -0.0069(17) C206 0.044(2) 0.033(2) 0.068(3) -0.0058(19) 0.034(2) 0.0029(16) C208 0.054(2) 0.038(2) 0.048(2) -0.0075(17) 0.0318(19) -0.0071(17) C209 0.059(3) 0.061(3) 0.043(2) 0.002(2) 0.016(2) -0.011(2) C210 0.042(2) 0.053(3) 0.054(3) 0.007(2) 0.0086(19) 0.0006(19) C211 0.041(2) 0.041(2) 0.070(3) -0.007(2) 0.031(2) -0.0065(17) C212 0.043(2) 0.036(2) 0.044(2) -0.0042(16) 0.0237(17) -0.0056(16) C213 0.058(2) 0.046(2) 0.041(2) 0.0017(18) 0.0209(19) -0.0102(19) C214 0.062(3) 0.033(2) 0.056(2) 0.0023(19) 0.026(2) -0.0007(19) C215 0.066(3) 0.032(2) 0.066(3) -0.0122(19) 0.041(2) -0.0064(18) B10 0.030(2) 0.024(2) 0.033(2) 0.0011(19) 0.0152(19) 0.0023(18) B11 0.028(9) 0.026(10) 0.022(8) 0.005(7) 0.015(7) 0.003(7) B20 0.0339 0.0252 0.0372 0.0019 0.0175 0.0018 N1 0.0323(14) 0.0255(14) 0.0392(16) -0.0048(12) 0.0176(13) -0.0021(11) N2 0.0324(14) 0.0236(14) 0.0425(16) -0.0001(12) 0.0197(13) 0.0012(11) _refine_ls_extinction_coef 200(30) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 2.59(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F20 . C20 . 1.365(6) yes F21 . C21 . 1.367(10) yes F30 . C30 . 1.341(6) yes F31 . C31 . 1.340(10) yes F40 . C40 . 1.340(5) yes F41 . C41 . 1.350(10) yes F50 . C50 . 1.346(5) yes F51 . C51 . 1.348(10) yes F60 . C60 . 1.350(4) yes F61 . C61 . 1.361(9) yes F80 . C80 . 1.350(6) yes F81 . C81 . 1.353(10) yes F90 . C90 . 1.339(7) yes F91 . C91 . 1.337(10) yes F100 . C100 . 1.352(6) yes F101 . C101 . 1.359(10) yes F110 . C110 . 1.345(6) yes F111 . C111 . 1.351(10) yes F120 . C120 . 1.357(5) yes F121 . C121 . 1.361(10) yes F140 . C140 . 1.347(5) yes F141 . C141 . 1.350(9) yes F150 . C150 . 1.352(5) yes F151 . C151 . 1.360(10) yes F160 . C160 . 1.343(5) yes F161 . C161 . 1.348(9) yes F170 . C170 . 1.341(5) yes F171 . C171 . 1.346(10) yes F180 . C180 . 1.348(5) yes F181 . C181 . 1.354(10) yes C10 . C20 . 1.388(7) yes C10 . C60 . 1.384(7) yes C10 . B10 . 1.637(7) yes C11 . C21 . 1.34(3) yes C11 . C61 . 1.40(3) yes C11 . B11 . 1.66(3) yes C20 . C30 . 1.383(9) yes C21 . C31 . 1.41(4) yes C30 . C40 . 1.366(10) yes C31 . C41 . 1.30(4) yes C40 . C50 . 1.366(10) yes C41 . C51 . 1.44(5) yes C50 . C60 . 1.371(7) yes C51 . C61 . 1.32(4) yes C70 . C80 . 1.381(11) yes C70 . C120 . 1.396(9) yes C70 . B10 . 1.634(7) yes C71 . C81 . 1.39(5) yes C71 . C121 . 1.36(4) yes C71 . B11 . 1.66(3) yes C80 . C90 . 1.390(15) yes C81 . C91 . 1.40(7) yes C90 . C100 . 1.381(12) yes C91 . C101 . 1.43(6) yes C100 . C110 . 1.357(8) yes C110 . C120 . 1.364(10) yes C111 . C121 . 1.36(4) yes C130 . C140 . 1.391(7) yes C130 . C180 . 1.381(7) yes C130 . B10 . 1.629(7) yes C131 . C141 . 1.36(3) yes C131 . C181 . 1.45(3) yes C131 . B11 . 1.64(3) yes C140 . C150 . 1.384(7) yes C141 . C151 . 1.39(3) yes C150 . C160 . 1.364(8) yes C151 . C161 . 1.38(4) yes C160 . C170 . 1.370(9) yes C161 . C171 . 1.25(5) yes C170 . C180 . 1.388(9) yes C171 . C181 . 1.33(4) yes C200 . B20 . 1.574(5) yes C200 . N1 . 1.352(4) yes C200 . N2 . 1.340(4) yes C201 . N1 . 1.461(4) yes C201 . H2011 . 0.952 no C201 . H2012 . 0.952 no C201 . H2013 . 0.950 no C202 . C203 . 1.488(5) yes C202 . C204 . 1.356(5) yes C202 . N1 . 1.370(4) yes C203 . H2031 . 0.969 no C203 . H2032 . 0.959 no C203 . H2033 . 0.949 no C204 . C205 . 1.482(5) yes C204 . N2 . 1.376(4) yes C205 . H2051 . 0.954 no C205 . H2052 . 0.971 no C205 . H2053 . 0.955 no C206 . N2 . 1.468(4) yes C206 . H2061 . 0.964 no C206 . H2062 . 0.958 no C206 . H2063 . 0.962 no C208 . C209 . 1.529(6) yes C208 . C215 . 1.550(5) yes C208 . B20 . 1.549(5) yes C208 . H2081 . 0.993 no C209 . C210 . 1.536(6) yes C209 . H2091 . 0.981 no C209 . H2092 . 0.970 no C210 . C211 . 1.504(6) yes C210 . H2101 . 0.983 no C210 . H2102 . 0.983 no C211 . C212 . 1.557(5) yes C211 . H2111 . 0.972 no C211 . H2112 . 0.978 no C212 . C213 . 1.538(5) yes C212 . B20 . 1.562(5) yes C212 . H2121 . 0.990 no C213 . C214 . 1.525(5) yes C213 . H2131 . 0.992 no C213 . H2132 . 0.963 no C214 . C215 . 1.527(5) yes C214 . H2141 . 0.983 no C214 . H2142 . 0.993 no C215 . H2151 . 0.971 no C215 . H2152 . 0.977 no B10 . H1 . 1.148 no B11 . H2 . 1.204 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 C20 . C10 . C60 . 112.8(5) yes C20 . C10 . B10 . 119.9(5) yes C60 . C10 . B10 . 127.3(6) yes C21 . C11 . C61 . 114.1(17) yes C21 . C11 . B11 . 121(2) yes C61 . C11 . B11 . 124.6(19) yes F20 . C20 . C10 . 119.1(6) yes F20 . C20 . C30 . 116.1(6) yes C10 . C20 . C30 . 124.7(6) yes F21 . C21 . C11 . 126(3) yes F21 . C21 . C31 . 108(3) yes C11 . C21 . C31 . 124.9(17) yes C20 . C30 . F30 . 120.8(7) yes C20 . C30 . C40 . 119.1(6) yes F30 . C30 . C40 . 120.1(7) yes C21 . C31 . F31 . 126(3) yes C21 . C31 . C41 . 116.9(19) yes F31 . C31 . C41 . 116(3) yes F40 . C40 . C30 . 119.6(7) yes F40 . C40 . C50 . 121.5(6) yes C30 . C40 . C50 . 118.9(5) yes F41 . C41 . C31 . 128(3) yes F41 . C41 . C51 . 110(3) yes C31 . C41 . C51 . 122.0(19) yes F50 . C50 . C40 . 119.7(6) yes F50 . C50 . C60 . 120.1(6) yes C40 . C50 . C60 . 120.2(5) yes C41 . C51 . F51 . 126(4) yes C41 . C51 . C61 . 116.6(15) yes F51 . C51 . C61 . 118(3) yes F60 . C60 . C10 . 119.4(6) yes F60 . C60 . C50 . 116.4(6) yes C10 . C60 . C50 . 124.3(4) yes C11 . C61 . F61 . 114(2) yes C11 . C61 . C51 . 124.7(16) yes F61 . C61 . C51 . 122(3) yes C80 . C70 . C120 . 113.1(5) yes C80 . C70 . B10 . 119.3(5) yes C120 . C70 . B10 . 127.5(5) yes C80 . C70 . B11 . 136.7(7) yes C120 . C70 . B11 . 91.3(7) yes C81 . C71 . C121 . 114(2) yes C81 . C71 . B11 . 127.7(20) yes C121 . C71 . B11 . 118.2(19) yes F80 . C80 . C70 . 119.4(7) yes F80 . C80 . C90 . 116.5(8) yes C70 . C80 . C90 . 124.1(6) yes F81 . C81 . C91 . 114(3) yes C71 . C81 . C91 . 127(2) yes C80 . C90 . F90 . 119.8(8) yes C80 . C90 . C100 . 118.8(6) yes F90 . C90 . C100 . 121.3(9) yes C81 . C91 . F91 . 121(5) yes C81 . C91 . C101 . 112(2) yes F91 . C91 . C101 . 124(5) yes F100 . C100 . C90 . 118.6(7) yes F100 . C100 . C110 . 121.8(7) yes C90 . C100 . C110 . 119.6(6) yes C91 . C101 . F101 . 114(4) yes C91 . C101 . C111 . 119(2) yes F101 . C101 . C111 . 124(4) yes F110 . C110 . C100 . 119.0(7) yes F110 . C110 . C120 . 121.5(6) yes C100 . C110 . C120 . 119.5(6) yes F111 . C111 . C101 . 115(3) yes F111 . C111 . C121 . 122(3) yes C101 . C111 . C121 . 122(2) yes F120 . C120 . C70 . 120.1(6) yes F120 . C120 . C110 . 115.1(6) yes C70 . C120 . C110 . 124.8(5) yes F121 . C121 . C71 . 121(3) yes F121 . C121 . C111 . 116(3) yes C71 . C121 . C111 . 122.6(18) yes C140 . C130 . C180 . 114.1(4) yes C140 . C130 . B10 . 119.8(4) yes C180 . C130 . B10 . 126.1(5) yes C141 . C131 . C181 . 114.1(17) yes C141 . C131 . B11 . 124.1(19) yes C181 . C131 . B11 . 121.9(18) yes C130 . C140 . F140 . 119.0(5) yes C130 . C140 . C150 . 123.0(4) yes F140 . C140 . C150 . 118.0(5) yes F141 . C141 . C131 . 123(2) yes F141 . C141 . C151 . 115(2) yes C131 . C141 . C151 . 121.6(16) yes F150 . C150 . C140 . 119.3(5) yes F150 . C150 . C160 . 120.8(5) yes C140 . C150 . C160 . 120.0(5) yes F151 . C151 . C141 . 121(3) yes F151 . C151 . C161 . 119(3) yes C141 . C151 . C161 . 119.5(16) yes F160 . C160 . C150 . 118.8(5) yes F160 . C160 . C170 . 121.2(5) yes C150 . C160 . C170 . 119.9(5) yes F161 . C161 . C151 . 119(3) yes F161 . C161 . C171 . 121(3) yes C151 . C161 . C171 . 119.9(18) yes F170 . C170 . C160 . 119.2(6) yes F170 . C170 . C180 . 122.5(5) yes C160 . C170 . C180 . 118.4(5) yes F171 . C171 . C161 . 124(3) yes F171 . C171 . C181 . 111(3) yes C161 . C171 . C181 . 124(2) yes C170 . C180 . F180 . 114.4(5) yes C170 . C180 . C130 . 124.5(5) yes F180 . C180 . C130 . 121.1(5) yes C131 . C181 . F181 . 112(3) yes C131 . C181 . C171 . 120.6(17) yes F181 . C181 . C171 . 127(3) yes B20 . C200 . N1 . 127.3(3) yes B20 . C200 . N2 . 127.3(3) yes N1 . C200 . N2 . 105.3(3) yes N1 . C201 . H2011 . 110.7 no N1 . C201 . H2012 . 111.5 no H2011 . C201 . H2012 . 109.1 no N1 . C201 . H2013 . 108.6 no H2011 . C201 . H2013 . 108.2 no H2012 . C201 . H2013 . 108.6 no C203 . C202 . C204 . 129.8(3) yes C203 . C202 . N1 . 123.0(3) yes C204 . C202 . N1 . 107.2(3) yes C202 . C203 . H2031 . 110.4 no C202 . C203 . H2032 . 109.8 no H2031 . C203 . H2032 . 108.6 no C202 . C203 . H2033 . 109.6 no H2031 . C203 . H2033 . 108.9 no H2032 . C203 . H2033 . 109.6 no C202 . C204 . C205 . 131.3(3) yes C202 . C204 . N2 . 106.0(3) yes C205 . C204 . N2 . 122.8(3) yes C204 . C205 . H2051 . 110.1 no C204 . C205 . H2052 . 110.6 no H2051 . C205 . H2052 . 108.9 no C204 . C205 . H2053 . 108.6 no H2051 . C205 . H2053 . 108.1 no H2052 . C205 . H2053 . 110.5 no N2 . C206 . H2061 . 110.3 no N2 . C206 . H2062 . 110.0 no H2061 . C206 . H2062 . 109.6 no N2 . C206 . H2063 . 108.8 no H2061 . C206 . H2063 . 108.4 no H2062 . C206 . H2063 . 109.7 no C209 . C208 . C215 . 114.4(3) yes C209 . C208 . B20 . 102.0(3) yes C215 . C208 . B20 . 111.6(3) yes C209 . C208 . H2081 . 107.7 no C215 . C208 . H2081 . 110.1 no B20 . C208 . H2081 . 110.7 no C208 . C209 . C210 . 114.9(3) yes C208 . C209 . H2091 . 106.8 no C210 . C209 . H2091 . 107.0 no C208 . C209 . H2092 . 109.3 no C210 . C209 . H2092 . 109.1 no H2091 . C209 . H2092 . 109.6 no C209 . C210 . C211 . 114.1(3) yes C209 . C210 . H2101 . 109.8 no C211 . C210 . H2101 . 108.7 no C209 . C210 . H2102 . 107.9 no C211 . C210 . H2102 . 108.7 no H2101 . C210 . H2102 . 107.5 no C210 . C211 . C212 . 115.7(3) yes C210 . C211 . H2111 . 107.8 no C212 . C211 . H2111 . 107.7 no C210 . C211 . H2112 . 108.1 no C212 . C211 . H2112 . 107.3 no H2111 . C211 . H2112 . 110.2 no C211 . C212 . C213 . 113.6(3) yes C211 . C212 . B20 . 109.9(3) yes C213 . C212 . B20 . 104.2(3) yes C211 . C212 . H2121 . 111.3 no C213 . C212 . H2121 . 107.5 no B20 . C212 . H2121 . 110.2 no C212 . C213 . C214 . 115.0(3) yes C212 . C213 . H2131 . 108.3 no C214 . C213 . H2131 . 107.9 no C212 . C213 . H2132 . 108.2 no C214 . C213 . H2132 . 108.1 no H2131 . C213 . H2132 . 109.3 no C213 . C214 . C215 . 113.2(3) yes C213 . C214 . H2141 . 109.4 no C215 . C214 . H2141 . 109.1 no C213 . C214 . H2142 . 107.9 no C215 . C214 . H2142 . 108.1 no H2141 . C214 . H2142 . 109.0 no C208 . C215 . C214 . 115.9(3) yes C208 . C215 . H2151 . 109.6 no C214 . C215 . H2151 . 108.3 no C208 . C215 . H2152 . 106.1 no C214 . C215 . H2152 . 107.5 no H2151 . C215 . H2152 . 109.3 no C10 . B10 . C70 . 111.8(4) yes C10 . B10 . C130 . 112.6(4) yes C70 . B10 . C130 . 113.8(4) yes C10 . B10 . H1 . 106.1 no C70 . B10 . H1 . 109.8 no C130 . B10 . H1 . 102.0 no C11 . B11 . C71 . 109.5(15) yes C11 . B11 . C131 . 114.7(14) yes C71 . B11 . C131 . 116.4(15) yes C11 . B11 . H2 . 114.6 no C71 . B11 . H2 . 97.7 no C131 . B11 . H2 . 102.6 no C200 . B20 . C212 . 124.9(3) yes C200 . B20 . C208 . 123.0(3) yes C212 . B20 . C208 . 112.0(3) yes C201 . N1 . C202 . 124.0(3) yes C201 . N1 . C200 . 125.4(3) yes C202 . N1 . C200 . 110.3(3) yes C206 . N2 . C204 . 123.0(3) yes C206 . N2 . C200 . 125.6(3) yes C204 . N2 . C200 . 111.2(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 20/01/14 at 17:43:34 # #LIST 12 BLOCK SCALE X'S F(20, U'S, OCC) UNTIL C(181) CONT C(200, U'S) UNTIL C(215) CONT B(10, U'S, OCC) UNTIL B(11) CONT N(1, U'S) UNTIL N(2) CONT EXTPARAM EQUIV F(20, OCC), F(21, OCC), F(30, OCC), F(31, OCC) CONT F(40, OCC), F(41, OCC), F(50, OCC), F(51, OCC) CONT F(60, OCC), F(61, OCC), F(80, OCC), F(81, OCC) CONT F(90, OCC), F(91, OCC), F(100, OCC), F(101, OCC) CONT F(110, OCC), F(111, OCC), F(120, OCC), F(121, OCC) CONT F(140, OCC), F(141, OCC), F(150, OCC), F(151, OCC) CONT F(160, OCC), F(161, OCC), F(170, OCC), F(171, OCC) CONT F(180, OCC), F(181, OCC), C(10, OCC), C(11, OCC) CONT C(20, OCC), C(21, OCC), C(30, OCC), C(31, OCC) CONT C(40, OCC), C(41, OCC), C(50, OCC), C(51, OCC) CONT C(60, OCC), C(61, OCC), C(70, OCC), C(71, OCC) CONT C(80, OCC), C(81, OCC), C(90, OCC), C(91, OCC) CONT C(100, OCC), C(101, OCC), C(110, OCC), C(111, OCC) CONT C(120, OCC), C(121, OCC), C(130, OCC), C(131, OCC) CONT C(140, OCC), C(141, OCC), C(150, OCC), C(151, OCC) CONT C(160, OCC), C(161, OCC), C(170, OCC), C(171, OCC) CONT C(180, OCC), C(181, OCC), B(10, OCC), B(11, OCC) WEIGHT -1 F(21, OCC), F(31, OCC), F(41, OCC), F(51, OCC) CONT F(61, OCC), F(81, OCC), F(91, OCC), F(101, OCC) CONT F(111, OCC), F(121, OCC), F(141, OCC), F(151, OCC) CONT F(161, OCC), F(171, OCC), F(181, OCC), C(11, OCC) CONT C(21, OCC), C(31, OCC) C(41, OCC), C(51, OCC) CONT C(61, OCC), C(71, OCC), C(81, OCC), C(91, OCC) CONT C(101, OCC), C(111, OCC), C(121, OCC), C(131, OCC) CONT C(141, OCC), C(151, OCC), C(161, OCC), C(171, OCC), C(181, OCC) CONT B(11, OCC) RIDE B ( 10,X'S) H ( 1,X'S) RIDE B ( 11,X'S) H ( 2,X'S) RIDE C ( 201,X'S) H (2011,X'S) H (2012,X'S) H (2013,X'S) RIDE C ( 203,X'S) H (2031,X'S) H (2032,X'S) H (2033,X'S) RIDE C ( 205,X'S) H (2051,X'S) H (2052,X'S) H (2053,X'S) RIDE C ( 206,X'S) H (2061,X'S) H (2062,X'S) H (2063,X'S) RIDE C ( 208,X'S) H (2081,X'S) RIDE C ( 209,X'S) H (2091,X'S) H (2092,X'S) RIDE C ( 210,X'S) H (2101,X'S) H (2102,X'S) RIDE C ( 211,X'S) H (2111,X'S) H (2112,X'S) RIDE C ( 212,X'S) H (2121,X'S) RIDE C ( 213,X'S) H (2131,X'S) H (2132,X'S) RIDE C ( 214,X'S) H (2141,X'S) H (2142,X'S) RIDE C ( 215,X'S) H (2151,X'S) H (2152,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 20/01/14 at 17:43:34 # #LIST 16 NO DIST 0.0, 0.01 = MEAN C(20) TO F(20), C(21) TO F(21) DIST 0.0, 0.01 = MEAN C(30) TO F(30), C(31) TO F(31) DIST 0.0, 0.01 = MEAN C(40) TO F(40), C(41) TO F(41) DIST 0.0, 0.01 = MEAN C(50) TO F(50), C(51) TO F(51) DIST 0.0, 0.01 = MEAN C(60) TO F(60), C(61) TO F(61) REM DIST 0.0, 0.01 = MEAN C(80) TO F(80), C(81) TO F(81) DIST 0.0, 0.01 = MEAN C(90) TO F(90), C(91) TO F(91) DIST 0.0, 0.01 = MEAN C(100) TO F(100), C(101) TO F(101) DIST 0.0, 0.01 = MEAN C(110) TO F(110), C(111) TO F(111) DIST 0.0, 0.01 = MEAN C(120) TO F(120), C(121) TO F(121) REM DIST 0.0, 0.01 = MEAN C(140) TO F(140), C(141) TO F(141) DIST 0.0, 0.01 = MEAN C(150) TO F(150), C(151) TO F(151) DIST 0.0, 0.01 = MEAN C(160) TO F(160), C(161) TO F(161) DIST 0.0, 0.01 = MEAN C(170) TO F(170), C(171) TO F(171) DIST 0.0, 0.01 = MEAN C(180) TO F(180), C(181) TO F(181) REM U(IJ) 0.0, 0.02 = C(10) TO C(11) U(IJ) 0.0, 0.02 = C(20) TO C(21) U(IJ) 0.0, 0.02 = C(30) TO C(31) U(IJ) 0.0, 0.01 = C(40) TO C(41) U(IJ) 0.0, 0.01 = C(50) TO C(51) U(IJ) 0.0, 0.02 = C(60) TO C(61) U(IJ) 0.0, 0.02 = C(70) TO C(71) U(IJ) 0.0, 0.02 = C(80) TO C(81) U(IJ) 0.0, 0.02 = C(90) TO C(91) U(IJ) 0.0, 0.01 = C(100) TO C(101) U(IJ) 0.0, 0.02 = C(110) TO C(111) U(IJ) 0.0, 0.02 = C(120) TO C(121) U(IJ) 0.0, 0.02 = C(130) TO C(131) U(IJ) 0.0, 0.02 = C(140) TO C(141) U(IJ) 0.0, 0.01 = C(150) TO C(151) U(IJ) 0.0, 0.01 = C(160) TO C(161) U(IJ) 0.0, 0.01 = C(170) TO C(171) U(IJ) 0.0, 0.02 = C(180) TO C(181) REM U(IJ) 0.0, 0.02 = F(20) TO F(21) U(IJ) 0.0, 0.02 = F(30) TO F(31) U(IJ) 0.0, 0.02 = F(40) TO F(41) U(IJ) 0.0, 0.02 = F(50) TO F(51) U(IJ) 0.0, 0.02 = F(60) TO F(61) U(IJ) 0.0, 0.02 = F(80) TO F(81) U(IJ) 0.0, 0.02 = F(90) TO F(91) U(IJ) 0.0, 0.02 = F(100) TO F(101) U(IJ) 0.0, 0.02 = F(110) TO F(111) U(IJ) 0.0, 0.02 = F(120) TO F(121) U(IJ) 0.0, 0.02 = F(140) TO F(141) U(IJ) 0.0, 0.02 = F(150) TO F(151) U(IJ) 0.0, 0.02 = F(160) TO F(161) U(IJ) 0.0, 0.02 = F(170) TO F(171) U(IJ) 0.0, 0.02 = F(180) TO F(181) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _chemical_name_systematic '[9-BBN(i-DCDM)][HBCF]' _chemical_properties_physical 'Air-sensitive, Moisture-sensitive' ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 1429288' _audit_update_record ; 2015-10-28 deposited with the CCDC. 2016-02-12 downloaded from the CCDC. ; _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 7.3696(5) _cell_length_b 11.5512(8) _cell_length_c 17.0873(9) _cell_angle_alpha 90 _cell_angle_beta 93.641(5) _cell_angle_gamma 90 _cell_volume 1451.65(16) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C18.75 H33.75 B1.25 N2.50 # Dc = 1.41 Fooo = 544.00 Mu = 0.81 M = 307.75 # Found Formula = C15 H27 B1 N2 # Dc = 1.13 FOOO = 544.00 Mu = 0.65 M = 246.20 _chemical_formula_sum 'C15 H27 B1 N2' _chemical_formula_moiety 'C15 H27 B1 N2' _chemical_compound_source 'University of Manchester' _chemical_formula_weight 246.20 _cell_measurement_temperature 150.01(13) _cell_measurement_reflns_used 1616 _cell_measurement_theta_min 3.7180 _cell_measurement_theta_max 28.1220 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.32 _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.065 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_T_min 0.82417 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_detector_area_resol_mean 8.0714 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -79.00 -40.00 1.0000 77.3600 omega____ theta____ kappa____ phi______ frames - -20.7110 -178.0000 -180.0000 39 #__ type_ start__ end____ width___ exp.time_ 2 omega -2.00 85.00 1.0000 77.3600 omega____ theta____ kappa____ phi______ frames - 21.3360 57.0000 150.0000 87 #__ type_ start__ end____ width___ exp.time_ 3 omega -47.00 52.00 1.0000 77.3600 omega____ theta____ kappa____ phi______ frames - 21.3360 -77.0000 0.0000 99 ; _diffrn_measurement_method '\w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrysAlisPro, Agilent Technologies,' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies,' _computing_data_reduction 'CrysAlisPro, Agilent Technologies,' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'Ortep-3 for Windows: Farrugia, 2012' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150.01(13) _diffrn_reflns_number 5165 _reflns_number_total 2652 _diffrn_reflns_av_R_equivalents 0.040 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2652 # Theoretical number of reflections is about 5311 _diffrn_reflns_theta_min 2.969 _diffrn_reflns_theta_max 25.340 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.340 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _oxford_diffrn_Wilson_B_factor 1.69 _oxford_diffrn_Wilson_scale 2.70 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.44 _refine_diff_density_max 0.50 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2642 _refine_ls_number_restraints 0 _refine_ls_number_parameters 163 _oxford_refine_ls_R_factor_ref 0.0862 _refine_ls_wR_factor_ref 0.1277 _refine_ls_goodness_of_fit_ref 0.9866 _refine_ls_shift/su_max 0.0002395 _refine_ls_shift/su_mean 0.0000288 # The values computed with all filters except I/sigma _oxford_reflns_number_all 2642 _refine_ls_R_factor_all 0.0862 _refine_ls_wR_factor_all 0.1277 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1810 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_gt 0.1162 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.09P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.5353(2) 0.86322(16) 0.58505(9) 0.0193 1.0000 Uani . . . . . . C2 C 0.6405(3) 0.7749(2) 0.56162(11) 0.0190 1.0000 Uani . . . . . . N3 N 0.5503(2) 0.73582(17) 0.49502(9) 0.0210 1.0000 Uani . . . . . . C4 C 0.3898(3) 0.7974(2) 0.47830(12) 0.0249 1.0000 Uani . . . . . . C5 C 0.3812(3) 0.8781(2) 0.53439(12) 0.0236 1.0000 Uani . . . . . . C6 C 0.2401(3) 0.9680(2) 0.54790(15) 0.0356 1.0000 Uani . . . . . . C7 C 0.2594(3) 0.7672(3) 0.41071(14) 0.0389 1.0000 Uani . . . . . . C8 C 0.6179(3) 0.6476(2) 0.44304(12) 0.0297 1.0000 Uani . . . . . . B9 B 0.8353(3) 0.7206(2) 0.59530(13) 0.0195 1.0000 Uani . . . . . . C10 C 0.8217(3) 0.5822(2) 0.61494(12) 0.0221 1.0000 Uani . . . . . . C11 C 1.0167(3) 0.5335(2) 0.62177(13) 0.0280 1.0000 Uani . . . . . . C12 C 1.1370(3) 0.5932(2) 0.68607(14) 0.0305 1.0000 Uani . . . . . . C13 C 1.1345(3) 0.7243(2) 0.67902(13) 0.0282 1.0000 Uani . . . . . . C14 C 0.9410(3) 0.7760(2) 0.67400(11) 0.0207 1.0000 Uani . . . . . . C15 C 0.8451(3) 0.7483(2) 0.75054(12) 0.0247 1.0000 Uani . . . . . . C16 C 0.6832(3) 0.6665(2) 0.73820(12) 0.0276 1.0000 Uani . . . . . . C17 C 0.7230(3) 0.5581(2) 0.69135(12) 0.0246 1.0000 Uani . . . . . . C18 C 0.5728(3) 0.9373(2) 0.65306(12) 0.0278 1.0000 Uani . . . . . . H61 H 0.1448 0.9605 0.5073 0.0517 1.0000 Uiso R . . . . . H63 H 0.2945 1.0448 0.5453 0.0510 1.0000 Uiso R . . . . . H62 H 0.1908 0.9560 0.5982 0.0512 1.0000 Uiso R . . . . . H71 H 0.1558 0.8178 0.4114 0.0569 1.0000 Uiso R . . . . . H73 H 0.3157 0.7778 0.3621 0.0561 1.0000 Uiso R . . . . . H72 H 0.2201 0.6875 0.4151 0.0572 1.0000 Uiso R . . . . . H81 H 0.5976 0.6740 0.3894 0.0409 1.0000 Uiso R . . . . . H83 H 0.7471 0.6370 0.4541 0.0407 1.0000 Uiso R . . . . . H82 H 0.5545 0.5758 0.4498 0.0408 1.0000 Uiso R . . . . . H101 H 0.7571 0.5402 0.5720 0.0251 1.0000 Uiso R . . . . . H112 H 1.0114 0.4504 0.6342 0.0320 1.0000 Uiso R . . . . . H111 H 1.0730 0.5438 0.5716 0.0316 1.0000 Uiso R . . . . . H121 H 1.0960 0.5716 0.7374 0.0345 1.0000 Uiso R . . . . . H122 H 1.2612 0.5644 0.6835 0.0351 1.0000 Uiso R . . . . . H132 H 1.2001 0.7570 0.7256 0.0322 1.0000 Uiso R . . . . . H131 H 1.1957 0.7468 0.6321 0.0311 1.0000 Uiso R . . . . . H141 H 0.9560 0.8616 0.6700 0.0236 1.0000 Uiso R . . . . . H152 H 0.8058 0.8191 0.7739 0.0292 1.0000 Uiso R . . . . . H151 H 0.9322 0.7106 0.7875 0.0290 1.0000 Uiso R . . . . . H161 H 0.6444 0.6429 0.7900 0.0303 1.0000 Uiso R . . . . . H162 H 0.5816 0.7095 0.7106 0.0309 1.0000 Uiso R . . . . . H171 H 0.7984 0.5051 0.7258 0.0276 1.0000 Uiso R . . . . . H172 H 0.6083 0.5183 0.6784 0.0267 1.0000 Uiso R . . . . . H182 H 0.5571 1.0177 0.6375 0.0388 1.0000 Uiso R . . . . . H181 H 0.6961 0.9246 0.6728 0.0394 1.0000 Uiso R . . . . . H183 H 0.4893 0.9185 0.6926 0.0389 1.0000 Uiso R . . . . . H1 H 0.9245 0.7371 0.5429 0.0318 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 N1 0.0193(9) 0.0201(12) 0.0185(8) 0.0023(8) 0.0017(7) 0.0030(8) C2 0.0195(11) 0.0220(14) 0.0154(9) 0.0027(9) 0.0012(8) -0.0007(10) N3 0.0234(10) 0.0228(12) 0.0163(8) 0.0010(8) -0.0026(7) -0.0002(9) C4 0.0193(11) 0.0296(16) 0.0250(11) 0.0065(10) -0.0043(9) 0.0002(10) C5 0.0166(11) 0.0260(15) 0.0280(11) 0.0098(10) 0.0004(9) 0.0011(10) C6 0.0251(13) 0.0368(18) 0.0450(14) 0.0093(13) 0.0044(10) 0.0111(12) C7 0.0348(14) 0.0442(19) 0.0352(13) 0.0055(12) -0.0165(11) -0.0020(13) C8 0.0392(14) 0.0327(17) 0.0167(10) -0.0051(10) -0.0012(9) 0.0012(12) B9 0.0164(12) 0.0233(16) 0.0189(11) 0.0016(10) 0.0007(9) 0.0035(11) C10 0.0200(11) 0.0242(15) 0.0216(10) -0.0004(10) -0.0020(8) 0.0029(10) C11 0.0263(12) 0.0230(15) 0.0347(12) 0.0058(11) 0.0026(9) 0.0061(11) C12 0.0161(11) 0.0379(18) 0.0366(13) 0.0129(12) -0.0041(9) 0.0042(11) C13 0.0206(12) 0.0353(17) 0.0281(11) 0.0063(11) -0.0046(9) -0.0057(11) C14 0.0206(11) 0.0194(14) 0.0219(10) 0.0023(9) -0.0012(8) -0.0032(10) C15 0.0276(12) 0.0286(16) 0.0173(10) 0.0004(9) -0.0024(8) -0.0028(11) C16 0.0289(12) 0.0315(16) 0.0229(11) 0.0033(10) 0.0043(9) -0.0031(11) C17 0.0212(11) 0.0243(16) 0.0281(11) 0.0040(10) -0.0009(9) -0.0025(10) C18 0.0347(13) 0.0232(15) 0.0257(11) -0.0036(10) 0.0028(9) 0.0046(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.711(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 N1 . C2 . 1.357(3) yes N1 . C5 . 1.394(3) yes N1 . C18 . 1.456(3) yes C2 . N3 . 1.358(3) yes C2 . B9 . 1.637(3) yes N3 . C4 . 1.394(3) yes N3 . C8 . 1.460(3) yes C4 . C5 . 1.341(3) yes C4 . C7 . 1.496(3) yes C5 . C6 . 1.498(3) yes C6 . H61 . 0.960 no C6 . H63 . 0.975 no C6 . H62 . 0.964 no C7 . H71 . 0.962 no C7 . H73 . 0.960 no C7 . H72 . 0.969 no C8 . H81 . 0.968 no C8 . H83 . 0.967 no C8 . H82 . 0.962 no B9 . C10 . 1.638(4) yes B9 . C14 . 1.641(3) yes B9 . H1 . 1.160 no C10 . C11 . 1.541(3) yes C10 . C17 . 1.559(3) yes C10 . H101 . 0.978 no C11 . C12 . 1.531(3) yes C11 . H112 . 0.985 no C11 . H111 . 0.984 no C12 . C13 . 1.519(4) yes C12 . H121 . 0.979 no C12 . H122 . 0.977 no C13 . C14 . 1.544(3) yes C13 . H132 . 0.980 no C13 . H131 . 0.979 no C14 . C15 . 1.559(3) yes C14 . H141 . 0.997 no C15 . C16 . 1.526(3) yes C15 . H152 . 0.964 no C15 . H151 . 0.974 no C16 . C17 . 1.525(3) yes C16 . H161 . 0.987 no C16 . H162 . 0.993 no C17 . H171 . 0.994 no C17 . H172 . 0.975 no C18 . H182 . 0.970 no C18 . H181 . 0.960 no C18 . H183 . 0.967 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 . N1 . C5 . 111.55(18) yes C2 . N1 . C18 . 126.50(17) yes C5 . N1 . C18 . 121.94(19) yes N1 . C2 . N3 . 103.79(17) yes N1 . C2 . B9 . 133.54(18) yes N3 . C2 . B9 . 122.62(19) yes C2 . N3 . C4 . 111.47(18) yes C2 . N3 . C8 . 125.01(18) yes C4 . N3 . C8 . 123.33(18) yes N3 . C4 . C5 . 106.63(18) yes N3 . C4 . C7 . 122.3(2) yes C5 . C4 . C7 . 131.0(2) yes N1 . C5 . C4 . 106.54(19) yes N1 . C5 . C6 . 122.4(2) yes C4 . C5 . C6 . 131.1(2) yes C5 . C6 . H61 . 108.0 no C5 . C6 . H63 . 109.4 no H61 . C6 . H63 . 109.5 no C5 . C6 . H62 . 110.0 no H61 . C6 . H62 . 109.3 no H63 . C6 . H62 . 110.5 no C4 . C7 . H71 . 108.7 no C4 . C7 . H73 . 110.2 no H71 . C7 . H73 . 108.7 no C4 . C7 . H72 . 110.0 no H71 . C7 . H72 . 109.6 no H73 . C7 . H72 . 109.6 no N3 . C8 . H81 . 108.5 no N3 . C8 . H83 . 109.8 no H81 . C8 . H83 . 108.4 no N3 . C8 . H82 . 110.0 no H81 . C8 . H82 . 109.8 no H83 . C8 . H82 . 110.3 no C2 . B9 . C10 . 112.47(18) yes C2 . B9 . C14 . 119.94(19) yes C10 . B9 . C14 . 104.17(17) yes C2 . B9 . H1 . 101.1 no C10 . B9 . H1 . 111.3 no C14 . B9 . H1 . 107.8 no B9 . C10 . C11 . 107.62(18) yes B9 . C10 . C17 . 112.55(18) yes C11 . C10 . C17 . 110.73(18) yes B9 . C10 . H101 . 111.3 no C11 . C10 . H101 . 106.4 no C17 . C10 . H101 . 108.0 no C10 . C11 . C12 . 112.65(19) yes C10 . C11 . H112 . 108.8 no C12 . C11 . H112 . 108.2 no C10 . C11 . H111 . 109.5 no C12 . C11 . H111 . 108.3 no H112 . C11 . H111 . 109.3 no C11 . C12 . C13 . 112.84(18) yes C11 . C12 . H121 . 109.3 no C13 . C12 . H121 . 108.8 no C11 . C12 . H122 . 108.4 no C13 . C12 . H122 . 110.0 no H121 . C12 . H122 . 107.3 no C12 . C13 . C14 . 113.38(19) yes C12 . C13 . H132 . 108.5 no C14 . C13 . H132 . 107.6 no C12 . C13 . H131 . 109.0 no C14 . C13 . H131 . 108.9 no H132 . C13 . H131 . 109.5 no C13 . C14 . B9 . 106.48(17) yes C13 . C14 . C15 . 109.90(17) yes B9 . C14 . C15 . 112.97(17) yes C13 . C14 . H141 . 106.3 no B9 . C14 . H141 . 112.3 no C15 . C14 . H141 . 108.6 no C14 . C15 . C16 . 113.80(17) yes C14 . C15 . H152 . 109.8 no C16 . C15 . H152 . 109.3 no C14 . C15 . H151 . 108.7 no C16 . C15 . H151 . 106.9 no H152 . C15 . H151 . 108.3 no C15 . C16 . C17 . 113.96(19) yes C15 . C16 . H161 . 108.4 no C17 . C16 . H161 . 108.7 no C15 . C16 . H162 . 108.4 no C17 . C16 . H162 . 109.0 no H161 . C16 . H162 . 108.2 no C16 . C17 . C10 . 114.12(19) yes C16 . C17 . H171 . 108.3 no C10 . C17 . H171 . 109.4 no C16 . C17 . H172 . 108.3 no C10 . C17 . H172 . 109.7 no H171 . C17 . H172 . 106.7 no N1 . C18 . H182 . 109.3 no N1 . C18 . H181 . 108.5 no H182 . C18 . H181 . 109.7 no N1 . C18 . H183 . 109.2 no H182 . C18 . H183 . 109.7 no H181 . C18 . H183 . 110.5 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 C18 . H181 . C14 . 141.04 0.960 2.490 3.293(3) yes _iucr_refine_instructions_details_constraints ; # # Punched on 01/04/14 at 14:29:49 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 6,X'S) H ( 61,X'S) H ( 63,X'S) H ( 62,X'S) RIDE C ( 7,X'S) H ( 71,X'S) H ( 73,X'S) H ( 72,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 83,X'S) H ( 82,X'S) RIDE B ( 9,X'S) H ( 1,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 112,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 13,X'S) H ( 132,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 152,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) RIDE C ( 17,X'S) H ( 171,X'S) H ( 172,X'S) RIDE C ( 18,X'S) H ( 182,X'S) H ( 181,X'S) H ( 183,X'S) END ; _iucr_refine_instructions_details_restraints ; # # Punched on 01/04/14 at 14:29:49 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _chemical_name_systematic 9-BBN(H)(IMe4) _chemical_properties_physical 'Air-sensitive, Moisture-sensitive' ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 1429289' _audit_update_record ; 2015-10-28 deposited with the CCDC. 2016-02-12 downloaded from the CCDC. ; # start Validation Reply Form _vrf_PLAT334_1 ; PROBLEM: Small Average Benzene C-C Dist. C25 -C30 1.37 Ang. RESPONSE: Additional refinement does not change the bond distnce, and fourier difference maps do not show an excess of electron density close to either carbon ; _vrf_PLAT410_1 ; PROBLEM: Short Intra H...H Contact H4 .. H11 .. 1.95 Ang. RESPONSE: H4 and H11 are part of a constrained bicyclic ring, brining them into close contact ; # Added during the CSD deposition process: Wednesday 28th of October 2015 11:24:53 AM # end Validation Reply Form _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 8.8757(6) _cell_length_b 20.3411(11) _cell_length_c 10.7976(7) _cell_angle_alpha 90 _cell_angle_beta 101.728(7) _cell_angle_gamma 90 _cell_volume 1908.7(2) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 '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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 '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' 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' _cell_formula_units_Z 2 # Given Formula = C34 H27 B2 Cl4.50 F15 N4 # Dc = 1.67 Fooo = 968.00 Mu = 4.53 M = 957.74 # Found Formula = C36 H27 B2 Cl4 F15 N4 # Dc = 1.68 FOOO = 968.00 Mu = 4.20 M = 964.04 _chemical_formula_sum 'C36 H27 B2 Cl4 F15 N4' _chemical_formula_moiety 'C36 H27 B2 Cl4 F15 N4' _chemical_compound_source ? _chemical_formula_weight 964.04 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 150.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.1 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.45 _exptl_crystal_density_diffrn 1.677 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.420 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_T_min 0.72395 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_detector_area_resol_mean 8.0714 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -79.00 -40.00 1.0000 77.3600 omega____ theta____ kappa____ phi______ frames - -20.7110 -178.0000 -180.0000 39 #__ type_ start__ end____ width___ exp.time_ 2 omega -2.00 85.00 1.0000 77.3600 omega____ theta____ kappa____ phi______ frames - 21.3360 57.0000 150.0000 87 #__ type_ start__ end____ width___ exp.time_ 3 omega -47.00 52.00 1.0000 77.3600 omega____ theta____ kappa____ phi______ frames - 21.3360 -77.0000 0.0000 99 ; _diffrn_measurement_method '\w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrysAlisPro, Agilent Technologies,' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies,' _computing_data_reduction 'CrysAlisPro, Agilent Technologies,' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'Ortep3 v. 2.02 (LJ Farrugia, 1997)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 8992 _reflns_number_total 7031 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections without Friedels Law is 7031 # Number of reflections with Friedels Law is 4522 # Theoretical number of reflections is about 5136 _diffrn_reflns_theta_min 3.374 _diffrn_reflns_theta_max 29.127 _diffrn_measured_fraction_theta_max 0.857 _diffrn_reflns_theta_full 26.260 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min -12 _reflns_limit_h_max 11 _reflns_limit_k_min -25 _reflns_limit_k_max 26 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 2.45 _oxford_diffrn_Wilson_scale 0.02 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.55 _refine_diff_density_max 0.54 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 7014 _refine_ls_number_restraints 1 _refine_ls_number_parameters 551 _oxford_refine_ls_R_factor_ref 0.0725 _refine_ls_wR_factor_ref 0.0879 _refine_ls_goodness_of_fit_ref 0.9775 _refine_ls_shift/su_max 0.0003049 _refine_ls_shift/su_mean 0.0000598 # The values computed with all filters except I/sigma _oxford_reflns_number_all 7014 _refine_ls_R_factor_all 0.0725 _refine_ls_wR_factor_all 0.0879 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5444 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_gt 0.0785 _refine_ls_abs_structure_Flack 0.00(5) _refine_ls_abs_structure_details 'Flack (1983), 2509 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 ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.40P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens H1 H 0.7092 0.6007 1.0523 0.0319 1.0000 Uiso R . . . . . H2 H 0.5619 0.6812 1.1414 0.0451 1.0000 Uiso R . . . . . H3 H 0.6302 0.7073 1.0260 0.0452 1.0000 Uiso R . . . . . H4 H 0.3192 0.6888 1.0320 0.0511 1.0000 Uiso R . . . . . H5 H 0.3987 0.7513 0.9840 0.0506 1.0000 Uiso R . . . . . H6 H 0.2387 0.6912 0.8141 0.0437 1.0000 Uiso R . . . . . H7 H 0.4111 0.7012 0.7965 0.0433 1.0000 Uiso R . . . . . H8 H 0.3231 0.5933 0.7483 0.0319 1.0000 Uiso R . . . . . H9 H 0.1721 0.5908 0.9130 0.0419 1.0000 Uiso R . . . . . H10 H 0.2524 0.5233 0.8927 0.0417 1.0000 Uiso R . . . . . H11 H 0.3137 0.6025 1.1091 0.0455 1.0000 Uiso R . . . . . H12 H 0.2940 0.5255 1.0987 0.0452 1.0000 Uiso R . . . . . H13 H 0.5546 0.5642 1.1863 0.0406 1.0000 Uiso R . . . . . H14 H 0.5418 0.5109 1.0761 0.0407 1.0000 Uiso R . . . . . H15 H 0.9578 0.6895 0.9040 0.0557 1.0000 Uiso R . . . . . H16 H 0.8309 0.7390 0.9344 0.0558 1.0000 Uiso R . . . . . H17 H 0.8373 0.6652 0.9843 0.0559 1.0000 Uiso R . . . . . H18 H 0.5320 0.5639 0.4964 0.0521 1.0000 Uiso R . . . . . H19 H 0.4698 0.5426 0.6172 0.0520 1.0000 Uiso R . . . . . H20 H 0.3999 0.6038 0.5367 0.0525 1.0000 Uiso R . . . . . H21 H 0.9663 0.4964 0.9282 0.0412 1.0000 Uiso R . . . . . H22 H 0.8906 0.5206 1.0403 0.0413 1.0000 Uiso R . . . . . H23 H 0.8715 0.5615 0.9169 0.0405 1.0000 Uiso R . . . . . H24 H 0.2875 0.4284 0.7857 0.0408 1.0000 Uiso R . . . . . H25 H 0.3423 0.4289 0.6581 0.0406 1.0000 Uiso R . . . . . H26 H 0.3092 0.4953 0.7195 0.0405 1.0000 Uiso R . . . . . F1 F 0.5977(3) 0.26546(12) 0.4773(2) 0.0368 1.0000 Uani . . . . . . F2 F 0.6726(3) 0.18590(12) 0.6759(2) 0.0402 1.0000 Uani . . . . . . F3 F 0.9478(3) 0.19676(11) 0.8373(2) 0.0392 1.0000 Uani . . . . . . F4 F 1.1602(3) 0.28434(13) 0.7859(3) 0.0463 1.0000 Uani . . . . . . F5 F 1.0922(3) 0.36289(12) 0.5856(2) 0.0404 1.0000 Uani . . . . . . F6 F 0.8803(3) 0.46311(13) 0.2258(2) 0.0478 1.0000 Uani . . . . . . F7 F 1.0100(5) 0.58114(14) 0.2673(3) 0.0737 1.0000 Uani . . . . . . F8 F 1.0634(3) 0.63503(12) 0.5048(3) 0.0501 1.0000 Uani . . . . . . F9 F 0.9782(3) 0.56760(12) 0.6963(2) 0.0434 1.0000 Uani . . . . . . F10 F 0.8582(3) 0.44817(12) 0.6588(2) 0.0365 1.0000 Uani . . . . . . F11 F 0.6616(3) 0.35085(13) 0.1340(2) 0.0475 1.0000 Uani . . . . . . F12 F 0.3661(4) 0.36683(16) 0.0263(3) 0.0639 1.0000 Uani . . . . . . F13 F 0.1613(3) 0.40993(17) 0.1636(3) 0.0665 1.0000 Uani . . . . . . F14 F 0.2587(3) 0.43713(16) 0.4151(3) 0.0613 1.0000 Uani . . . . . . F15 F 0.5535(3) 0.41705(13) 0.5267(2) 0.0391 1.0000 Uani . . . . . . Cl1 Cl 0.91362(14) 0.75937(6) 0.67722(12) 0.0397 1.0000 Uani . . . . . . Cl2 Cl 0.67880(13) 0.67595(6) 0.43082(10) 0.0379 1.0000 Uani . . . . . . Cl3 Cl 0.89171(13) 0.36626(6) 0.93501(11) 0.0375 1.0000 Uani . . . . . . Cl4 Cl 0.52043(14) 0.32284(6) 0.77663(11) 0.0375 1.0000 Uani . . . . . . N1 N 0.7531(4) 0.67440(16) 0.7948(3) 0.0239 1.0000 Uani . . . . . . N2 N 0.6036(4) 0.62401(15) 0.6429(3) 0.0237 1.0000 Uani . . . . . . N3 N 0.7370(4) 0.48150(15) 0.8991(3) 0.0209 1.0000 Uani . . . . . . N4 N 0.5082(4) 0.45454(16) 0.8055(3) 0.0230 1.0000 Uani . . . . . . B1 B 0.5501(6) 0.5862(2) 0.8702(5) 0.0244 1.0000 Uani . . . . . . B2 B 0.8031(5) 0.3725(2) 0.4047(4) 0.0232 1.0000 Uani . . . . . . C1 C 0.5970(5) 0.60517(19) 1.0214(4) 0.0266 1.0000 Uani . . . . . . C2 C 0.5544(5) 0.6774(2) 1.0503(4) 0.0374 1.0000 Uani . . . . . . C3 C 0.3965(6) 0.7036(2) 0.9830(4) 0.0422 1.0000 Uani . . . . . . C4 C 0.3476(5) 0.6795(2) 0.8475(4) 0.0369 1.0000 Uani . . . . . . C5 C 0.3641(5) 0.6042(2) 0.8363(4) 0.0265 1.0000 Uani . . . . . . C6 C 0.2712(5) 0.5682(2) 0.9231(4) 0.0345 1.0000 Uani . . . . . . C7 C 0.3404(5) 0.5633(2) 1.0661(4) 0.0371 1.0000 Uani . . . . . . C8 C 0.5144(5) 0.5561(2) 1.0953(4) 0.0338 1.0000 Uani . . . . . . C9 C 0.6405(5) 0.62817(19) 0.7722(4) 0.0244 1.0000 Uani . . . . . . C10 C 0.8529(5) 0.6934(2) 0.9155(4) 0.0376 1.0000 Uani . . . . . . C11 C 0.7812(5) 0.6997(2) 0.6818(4) 0.0300 1.0000 Uani . . . . . . C12 C 0.6902(5) 0.6682(2) 0.5895(4) 0.0261 1.0000 Uani . . . . . . C13 C 0.4918(5) 0.5796(2) 0.5672(4) 0.0350 1.0000 Uani . . . . . . C14 C 0.5957(5) 0.50747(19) 0.8523(4) 0.0221 1.0000 Uani . . . . . . C15 C 0.8786(5) 0.51755(19) 0.9498(4) 0.0273 1.0000 Uani . . . . . . C16 C 0.7358(5) 0.4142(2) 0.8841(4) 0.0263 1.0000 Uani . . . . . . C17 C 0.5947(5) 0.39738(19) 0.8257(4) 0.0266 1.0000 Uani . . . . . . C18 C 0.3472(4) 0.4516(2) 0.7357(4) 0.0273 1.0000 Uani . . . . . . C19 C 0.8366(5) 0.32165(19) 0.5237(4) 0.0242 1.0000 Uani . . . . . . C20 C 0.7403(4) 0.2736(2) 0.5523(4) 0.0237 1.0000 Uani . . . . . . C21 C 0.7742(5) 0.2311(2) 0.6526(4) 0.0250 1.0000 Uani . . . . . . C22 C 0.9155(5) 0.23514(19) 0.7333(4) 0.0279 1.0000 Uani . . . . . . C23 C 1.0199(5) 0.2797(2) 0.7080(4) 0.0292 1.0000 Uani . . . . . . C24 C 0.9812(5) 0.3208(2) 0.6054(4) 0.0284 1.0000 Uani . . . . . . C25 C 0.8674(4) 0.4479(2) 0.4405(4) 0.0226 1.0000 Uani . . . . . . C26 C 0.9079(5) 0.4862(2) 0.3470(4) 0.0310 1.0000 Uani . . . . . . C27 C 0.9726(6) 0.5474(2) 0.3651(5) 0.0393 1.0000 Uani . . . . . . C28 C 0.9991(6) 0.5748(2) 0.4831(5) 0.0341 1.0000 Uani . . . . . . C29 C 0.9563(5) 0.5407(2) 0.5793(4) 0.0269 1.0000 Uani . . . . . . C30 C 0.8924(5) 0.4789(2) 0.5565(4) 0.0246 1.0000 Uani . . . . . . C31 C 0.6209(5) 0.38085(18) 0.3370(4) 0.0239 1.0000 Uani . . . . . . C32 C 0.5657(5) 0.3697(2) 0.2099(4) 0.0322 1.0000 Uani . . . . . . C33 C 0.4148(6) 0.3786(2) 0.1514(4) 0.0419 1.0000 Uani . . . . . . C34 C 0.3098(6) 0.4004(3) 0.2185(5) 0.0413 1.0000 Uani . . . . . . C35 C 0.3573(5) 0.4135(2) 0.3458(5) 0.0372 1.0000 Uani . . . . . . C36 C 0.5136(5) 0.4032(2) 0.4010(4) 0.0282 1.0000 Uani . . . . . . H27 H 0.8730 0.3540 0.3277 0.0117 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 F1 0.0266(14) 0.0405(15) 0.0375(16) 0.0109(13) -0.0074(12) -0.0083(12) F2 0.0374(15) 0.0373(14) 0.0432(17) 0.0115(13) 0.0023(13) -0.0122(13) F3 0.0507(17) 0.0347(14) 0.0279(15) 0.0067(12) -0.0019(13) 0.0019(13) F4 0.0305(16) 0.0515(16) 0.0479(19) 0.0095(14) -0.0135(14) -0.0017(13) F5 0.0254(14) 0.0426(15) 0.0509(18) 0.0111(14) 0.0023(13) -0.0090(12) F6 0.076(2) 0.0455(16) 0.0265(15) 0.0009(13) 0.0209(15) -0.0107(16) F7 0.127(3) 0.053(2) 0.049(2) 0.0102(15) 0.038(2) -0.040(2) F8 0.061(2) 0.0314(15) 0.056(2) 0.0017(14) 0.0098(17) -0.0200(14) F9 0.0568(19) 0.0367(14) 0.0333(16) -0.0043(13) 0.0012(15) -0.0105(14) F10 0.0538(17) 0.0355(13) 0.0230(14) 0.0003(12) 0.0143(13) -0.0083(14) F11 0.0580(19) 0.0624(18) 0.0237(15) -0.0134(13) 0.0117(14) -0.0034(15) F12 0.062(2) 0.096(2) 0.0248(16) -0.0032(17) -0.0116(15) -0.0188(19) F13 0.0284(17) 0.104(2) 0.057(2) 0.0254(19) -0.0149(16) -0.0053(17) F14 0.0295(16) 0.108(3) 0.0485(19) 0.0176(18) 0.0124(14) 0.0217(17) F15 0.0313(15) 0.0635(17) 0.0229(14) -0.0030(13) 0.0061(12) 0.0115(13) Cl1 0.0376(7) 0.0369(6) 0.0459(7) 0.0074(6) 0.0118(6) -0.0121(5) Cl2 0.0359(7) 0.0549(7) 0.0242(6) 0.0098(6) 0.0089(5) 0.0024(6) Cl3 0.0379(7) 0.0382(6) 0.0352(7) 0.0031(5) 0.0043(6) 0.0134(5) Cl4 0.0474(7) 0.0249(5) 0.0412(7) -0.0036(5) 0.0116(6) -0.0065(5) N1 0.0261(19) 0.0255(18) 0.0200(19) -0.0016(15) 0.0044(16) -0.0080(17) N2 0.024(2) 0.0264(18) 0.0193(19) -0.0005(15) 0.0004(16) -0.0035(16) N3 0.0233(19) 0.0231(18) 0.0164(19) 0.0022(14) 0.0044(15) -0.0026(15) N4 0.0201(18) 0.0262(18) 0.0225(19) 0.0006(15) 0.0041(15) -0.0044(16) B1 0.029(3) 0.023(2) 0.021(3) 0.002(2) 0.006(2) -0.006(2) B2 0.024(2) 0.025(2) 0.022(3) -0.002(2) 0.007(2) -0.003(2) C1 0.029(2) 0.028(2) 0.021(2) -0.0035(19) 0.000(2) -0.002(2) C2 0.047(3) 0.035(3) 0.029(3) -0.003(2) 0.006(2) -0.004(2) C3 0.062(4) 0.030(2) 0.035(3) -0.004(2) 0.012(3) 0.010(3) C4 0.036(3) 0.032(2) 0.041(3) -0.002(2) 0.004(2) 0.005(2) C5 0.026(2) 0.033(2) 0.019(2) 0.0004(19) 0.000(2) 0.001(2) C6 0.028(3) 0.035(3) 0.044(3) -0.008(2) 0.017(2) -0.002(2) C7 0.045(3) 0.036(3) 0.036(3) 0.001(2) 0.021(3) 0.000(2) C8 0.039(3) 0.036(3) 0.031(3) 0.001(2) 0.016(2) -0.002(2) C9 0.024(2) 0.025(2) 0.023(2) 0.0006(18) 0.0034(19) -0.0037(19) C10 0.036(3) 0.039(3) 0.033(3) -0.006(2) -0.003(2) -0.016(2) C11 0.028(2) 0.031(2) 0.031(3) 0.002(2) 0.005(2) -0.005(2) C12 0.026(2) 0.032(2) 0.022(2) 0.0071(19) 0.007(2) 0.003(2) C13 0.035(3) 0.042(3) 0.025(3) -0.004(2) -0.001(2) -0.006(2) C14 0.021(2) 0.029(2) 0.016(2) 0.0011(18) 0.0030(19) -0.0039(18) C15 0.021(2) 0.036(2) 0.024(2) 0.001(2) 0.000(2) -0.0044(19) C16 0.030(2) 0.026(2) 0.024(2) 0.0059(19) 0.007(2) 0.004(2) C17 0.035(3) 0.020(2) 0.029(2) 0.0018(18) 0.014(2) 0.0006(19) C18 0.022(2) 0.029(2) 0.031(3) -0.001(2) 0.006(2) -0.007(2) C19 0.025(2) 0.025(2) 0.024(2) -0.0028(19) 0.0075(19) 0.003(2) C20 0.017(2) 0.027(2) 0.026(2) 0.0033(19) 0.0020(18) 0.0062(18) C21 0.024(2) 0.023(2) 0.028(3) -0.0009(19) 0.005(2) -0.0029(19) C22 0.037(3) 0.022(2) 0.024(2) 0.0011(18) 0.003(2) 0.008(2) C23 0.028(2) 0.024(2) 0.032(3) -0.0002(19) -0.002(2) 0.002(2) C24 0.024(2) 0.024(2) 0.038(3) -0.004(2) 0.009(2) -0.001(2) C25 0.020(2) 0.026(2) 0.023(2) 0.0027(19) 0.0060(18) 0.0037(19) C26 0.037(3) 0.039(3) 0.019(2) -0.001(2) 0.009(2) -0.003(2) C27 0.050(3) 0.034(3) 0.039(3) 0.014(2) 0.021(3) -0.012(2) C28 0.031(3) 0.027(2) 0.044(3) 0.007(2) 0.007(2) -0.005(2) C29 0.025(2) 0.032(2) 0.022(2) -0.004(2) 0.000(2) 0.002(2) C30 0.023(2) 0.030(2) 0.022(2) 0.0061(19) 0.006(2) -0.0003(19) C31 0.030(2) 0.022(2) 0.019(2) 0.0007(18) 0.0030(19) -0.0041(19) C32 0.035(3) 0.034(2) 0.028(3) 0.000(2) 0.007(2) -0.006(2) C33 0.044(3) 0.049(3) 0.026(3) 0.005(2) -0.007(2) -0.013(3) C34 0.031(3) 0.054(3) 0.033(3) 0.011(2) -0.006(2) -0.008(3) C35 0.028(3) 0.048(3) 0.037(3) 0.006(2) 0.009(2) -0.001(2) C36 0.031(2) 0.033(2) 0.020(2) 0.0039(19) 0.004(2) 0.000(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 7.70(11) 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 H1 . C1 . 0.989 no H2 . C2 . 0.976 no H3 . C2 . 0.982 no H4 . C3 . 0.996 no H5 . C3 . 0.969 no H6 . C4 . 0.989 no H7 . C4 . 0.970 no H8 . C5 . 0.972 no H9 . C6 . 0.978 no H10 . C6 . 0.973 no H11 . C7 . 0.976 no H12 . C7 . 0.972 no H13 . C8 . 0.988 no H14 . C8 . 0.985 no H15 . C10 . 0.967 no H16 . C10 . 0.978 no H17 . C10 . 0.972 no H18 . C13 . 0.962 no H19 . C13 . 0.968 no H20 . C13 . 0.952 no H21 . C15 . 0.959 no H22 . C15 . 0.963 no H23 . C15 . 0.960 no H24 . C18 . 0.955 no H25 . C18 . 0.950 no H26 . C18 . 0.954 no F1 . C20 . 1.367(4) yes F2 . C21 . 1.347(5) yes F3 . C22 . 1.350(5) yes F4 . C23 . 1.357(4) yes F5 . C24 . 1.356(5) yes F6 . C26 . 1.364(5) yes F7 . C27 . 1.356(5) yes F8 . C28 . 1.351(5) yes F9 . C29 . 1.354(5) yes F10 . C30 . 1.356(5) yes F11 . C32 . 1.351(5) yes F12 . C33 . 1.354(5) yes F13 . C34 . 1.345(5) yes F14 . C35 . 1.349(5) yes F15 . C36 . 1.361(4) yes Cl1 . C11 . 1.697(4) yes Cl2 . C12 . 1.703(4) yes Cl3 . C16 . 1.690(4) yes Cl4 . C17 . 1.695(4) yes N1 . C9 . 1.357(5) yes N1 . C10 . 1.471(5) yes N1 . C11 . 1.392(5) yes N2 . C9 . 1.371(5) yes N2 . C12 . 1.382(5) yes N2 . C13 . 1.463(5) yes N3 . C14 . 1.361(5) yes N3 . C15 . 1.462(5) yes N3 . C16 . 1.379(5) yes N4 . C14 . 1.363(5) yes N4 . C17 . 1.386(5) yes N4 . C18 . 1.475(5) yes B1 . C1 . 1.647(6) yes B1 . C5 . 1.658(6) yes B1 . C9 . 1.685(6) yes B1 . C14 . 1.672(6) yes B2 . C19 . 1.630(6) yes B2 . C25 . 1.654(6) yes B2 . C31 . 1.642(6) yes B2 . H27 . 1.195 no C1 . C2 . 1.563(6) yes C1 . C8 . 1.552(6) yes C2 . C3 . 1.538(6) yes C3 . C4 . 1.520(6) yes C4 . C5 . 1.545(6) yes C5 . C6 . 1.552(6) yes C6 . C7 . 1.545(6) yes C7 . C8 . 1.519(6) yes C11 . C12 . 1.315(5) yes C16 . C17 . 1.327(6) yes C19 . C20 . 1.374(5) yes C19 . C24 . 1.402(5) yes C20 . C21 . 1.371(5) yes C21 . C22 . 1.376(6) yes C22 . C23 . 1.363(6) yes C23 . C24 . 1.374(6) yes C25 . C26 . 1.379(6) yes C25 . C30 . 1.379(5) yes C26 . C27 . 1.369(6) yes C27 . C28 . 1.366(6) yes C28 . C29 . 1.366(6) yes C29 . C30 . 1.382(5) yes C31 . C32 . 1.380(5) yes C31 . C36 . 1.363(6) yes C32 . C33 . 1.372(6) yes C33 . C34 . 1.366(7) yes C34 . C35 . 1.379(6) yes C35 . C36 . 1.410(6) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C9 . N1 . C10 . 129.1(4) yes C9 . N1 . C11 . 110.8(3) yes C10 . N1 . C11 . 119.7(4) yes C9 . N2 . C12 . 110.3(3) yes C9 . N2 . C13 . 127.0(4) yes C12 . N2 . C13 . 122.7(4) yes C14 . N3 . C15 . 127.0(3) yes C14 . N3 . C16 . 110.9(3) yes C15 . N3 . C16 . 121.9(3) yes C14 . N4 . C17 . 110.4(3) yes C14 . N4 . C18 . 129.9(3) yes C17 . N4 . C18 . 119.7(3) yes C1 . B1 . C5 . 101.9(4) yes C1 . B1 . C9 . 116.5(3) yes C5 . B1 . C9 . 109.2(3) yes C1 . B1 . C14 . 108.7(3) yes C5 . B1 . C14 . 116.1(3) yes C9 . B1 . C14 . 104.8(3) yes C19 . B2 . C25 . 113.9(3) yes C19 . B2 . C31 . 114.9(4) yes C25 . B2 . C31 . 105.7(3) yes C19 . B2 . H27 . 108.1 no C25 . B2 . H27 . 104.5 no C31 . B2 . H27 . 109.1 no B1 . C1 . H1 . 110.3 no B1 . C1 . C2 . 113.3(3) yes H1 . C1 . C2 . 106.6 no B1 . C1 . C8 . 108.0(3) yes H1 . C1 . C8 . 108.5 no C2 . C1 . C8 . 110.0(4) yes C1 . C2 . H3 . 108.8 no C1 . C2 . H2 . 107.9 no H3 . C2 . H2 . 108.0 no C1 . C2 . C3 . 117.8(4) yes H3 . C2 . C3 . 105.4 no H2 . C2 . C3 . 108.5 no C2 . C3 . H4 . 107.7 no C2 . C3 . H5 . 109.1 no H4 . C3 . H5 . 108.2 no C2 . C3 . C4 . 113.4(4) yes H4 . C3 . C4 . 108.7 no H5 . C3 . C4 . 109.6 no C3 . C4 . H6 . 109.9 no C3 . C4 . H7 . 108.3 no H6 . C4 . H7 . 108.8 no C3 . C4 . C5 . 112.4(4) yes H6 . C4 . C5 . 108.1 no H7 . C4 . C5 . 109.3 no C4 . C5 . B1 . 108.0(3) yes C4 . C5 . H8 . 106.3 no B1 . C5 . H8 . 108.8 no C4 . C5 . C6 . 110.6(4) yes B1 . C5 . C6 . 112.9(3) yes H8 . C5 . C6 . 110.0 no C5 . C6 . H9 . 106.7 no C5 . C6 . H10 . 108.4 no H9 . C6 . H10 . 108.4 no C5 . C6 . C7 . 118.8(4) yes H9 . C6 . C7 . 107.9 no H10 . C6 . C7 . 106.4 no C6 . C7 . H11 . 109.8 no C6 . C7 . H12 . 107.6 no H11 . C7 . H12 . 108.2 no C6 . C7 . C8 . 113.2(4) yes H11 . C7 . C8 . 108.3 no H12 . C7 . C8 . 109.6 no C1 . C8 . C7 . 113.4(4) yes C1 . C8 . H13 . 107.0 no C7 . C8 . H13 . 109.7 no C1 . C8 . H14 . 109.3 no C7 . C8 . H14 . 109.3 no H13 . C8 . H14 . 108.0 no B1 . C9 . N2 . 124.2(3) yes B1 . C9 . N1 . 131.7(4) yes N2 . C9 . N1 . 103.9(3) yes N1 . C10 . H16 . 109.0 no N1 . C10 . H17 . 111.6 no H16 . C10 . H17 . 109.6 no N1 . C10 . H15 . 106.7 no H16 . C10 . H15 . 110.1 no H17 . C10 . H15 . 109.9 no N1 . C11 . Cl1 . 122.6(3) yes N1 . C11 . C12 . 107.0(4) yes Cl1 . C11 . C12 . 130.4(4) yes Cl2 . C12 . N2 . 123.7(3) yes Cl2 . C12 . C11 . 128.2(4) yes N2 . C12 . C11 . 108.0(4) yes N2 . C13 . H19 . 111.1 no N2 . C13 . H18 . 109.2 no H19 . C13 . H18 . 109.7 no N2 . C13 . H20 . 108.0 no H19 . C13 . H20 . 109.8 no H18 . C13 . H20 . 109.0 no B1 . C14 . N4 . 131.8(4) yes B1 . C14 . N3 . 123.7(3) yes N4 . C14 . N3 . 104.1(3) yes N3 . C15 . H22 . 108.8 no N3 . C15 . H23 . 110.0 no H22 . C15 . H23 . 107.5 no N3 . C15 . H21 . 111.2 no H22 . C15 . H21 . 110.4 no H23 . C15 . H21 . 108.8 no Cl3 . C16 . N3 . 123.2(3) yes Cl3 . C16 . C17 . 129.6(3) yes N3 . C16 . C17 . 107.2(4) yes N4 . C17 . Cl4 . 122.2(3) yes N4 . C17 . C16 . 107.3(4) yes Cl4 . C17 . C16 . 130.4(3) yes N4 . C18 . H24 . 108.8 no N4 . C18 . H26 . 109.0 no H24 . C18 . H26 . 110.3 no N4 . C18 . H25 . 109.7 no H24 . C18 . H25 . 109.1 no H26 . C18 . H25 . 109.9 no B2 . C19 . C20 . 127.3(4) yes B2 . C19 . C24 . 120.1(4) yes C20 . C19 . C24 . 112.4(4) yes F1 . C20 . C19 . 119.8(4) yes F1 . C20 . C21 . 114.8(4) yes C19 . C20 . C21 . 125.4(4) yes F2 . C21 . C20 . 122.0(4) yes F2 . C21 . C22 . 118.8(4) yes C20 . C21 . C22 . 119.2(4) yes F3 . C22 . C21 . 120.3(4) yes F3 . C22 . C23 . 120.9(4) yes C21 . C22 . C23 . 118.8(4) yes F4 . C23 . C22 . 119.9(4) yes F4 . C23 . C24 . 120.3(4) yes C22 . C23 . C24 . 119.8(4) yes C19 . C24 . F5 . 119.6(4) yes C19 . C24 . C23 . 124.2(4) yes F5 . C24 . C23 . 116.2(4) yes B2 . C25 . C26 . 118.8(4) yes B2 . C25 . C30 . 128.3(4) yes C26 . C25 . C30 . 112.9(4) yes F6 . C26 . C25 . 119.0(4) yes F6 . C26 . C27 . 116.0(4) yes C25 . C26 . C27 . 125.0(4) yes F7 . C27 . C26 . 120.7(4) yes F7 . C27 . C28 . 119.8(4) yes C26 . C27 . C28 . 119.5(4) yes F8 . C28 . C27 . 121.2(4) yes F8 . C28 . C29 . 120.1(4) yes C27 . C28 . C29 . 118.7(4) yes F9 . C29 . C28 . 119.7(4) yes F9 . C29 . C30 . 120.6(4) yes C28 . C29 . C30 . 119.7(4) yes F10 . C30 . C29 . 115.2(4) yes F10 . C30 . C25 . 120.5(4) yes C29 . C30 . C25 . 124.2(4) yes B2 . C31 . C32 . 122.9(4) yes B2 . C31 . C36 . 122.4(4) yes C32 . C31 . C36 . 114.6(4) yes F11 . C32 . C31 . 120.7(4) yes F11 . C32 . C33 . 115.8(4) yes C31 . C32 . C33 . 123.5(5) yes F12 . C33 . C32 . 121.3(5) yes F12 . C33 . C34 . 118.2(4) yes C32 . C33 . C34 . 120.5(5) yes F13 . C34 . C33 . 121.8(5) yes F13 . C34 . C35 . 119.0(5) yes C33 . C34 . C35 . 119.2(4) yes F14 . C35 . C34 . 121.3(4) yes F14 . C35 . C36 . 120.8(4) yes C34 . C35 . C36 . 117.9(5) yes C35 . C36 . F15 . 115.2(4) yes C35 . C36 . C31 . 124.4(4) yes F15 . C36 . C31 . 120.5(4) yes 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 C2 . H3 . C10 . 134.58 0.982 2.525 3.289(6) yes C6 . H10 . C18 . 135.68 0.973 2.508 3.275(6) yes C10 . H17 . C1 . 130.92 0.972 2.558 3.279(6) yes C18 . H26 . C5 . 134.02 0.954 2.548 3.283(6) yes _iucr_refine_instructions_details_constraints ; # # Punched on 10/02/15 at 15:32:31 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE B ( 2,X'S) H ( 27,X'S) RIDE C ( 1,X'S) H ( 1,X'S) RIDE C ( 2,X'S) H ( 3,X'S) H ( 2,X'S) RIDE C ( 3,X'S) H ( 4,X'S) H ( 5,X'S) RIDE C ( 4,X'S) H ( 6,X'S) H ( 7,X'S) RIDE C ( 5,X'S) H ( 8,X'S) RIDE C ( 6,X'S) H ( 9,X'S) H ( 10,X'S) RIDE C ( 7,X'S) H ( 11,X'S) H ( 12,X'S) RIDE C ( 8,X'S) H ( 13,X'S) H ( 14,X'S) RIDE C ( 10,X'S) H ( 16,X'S) H ( 17,X'S) H ( 15,X'S) RIDE C ( 13,X'S) H ( 19,X'S) H ( 18,X'S) H ( 20,X'S) RIDE C ( 15,X'S) H ( 22,X'S) H ( 23,X'S) H ( 21,X'S) RIDE C ( 18,X'S) H ( 24,X'S) H ( 26,X'S) H ( 25,X'S) END ; _iucr_refine_instructions_details_restraints ; # # Punched on 10/02/15 at 15:32:31 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _chemical_name_systematic '[9-BBN(I-DCDM)2][HBCF]' _chemical_properties_physical Moisture-sensitive ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 1440939' _audit_update_record ; 2015-12-07 deposited with the CCDC. 2016-02-12 downloaded from the CCDC. ; _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 15.2641(4) _cell_length_b 10.3890(3) _cell_length_c 19.5887(6) _cell_angle_alpha 90 _cell_angle_beta 92.115(3) _cell_angle_gamma 90 _cell_volume 3104.23(16) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 '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' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C13 H20 B1 Cl2 F0.10 N2 # Dc = 1.54 Fooo = 1584.00 Mu = 5.05 M = 719.83 # Found Formula = C12.80 H6.40 B0.40 Cl0.80 F6 N0.80 # Dc = 1.70 FOOO = 1584.00 Mu = 3.29 M = 795.18 _chemical_formula_sum 'C32 H16 B1 Cl2 F15 N2' _chemical_formula_moiety 'C27 H9 B F15, C5 H7 Cl2 N2' _chemical_compound_source ? _chemical_formula_weight 795.18 _cell_measurement_reflns_used 5488 _cell_measurement_theta_min 3.8530 _cell_measurement_theta_max 28.2190 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.2 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.4 _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.329 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_T_min 0.95025 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_device Serial _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -30.00 48.00 1.0000 2.5600 omega____ theta____ kappa____ phi______ frames - -17.7663 19.0000 60.0000 78 #__ type_ start__ end____ width___ exp.time_ 2 omega 34.00 87.00 1.0000 2.5600 omega____ theta____ kappa____ phi______ frames - 18.8601 77.0000 -60.0000 53 #__ type_ start__ end____ width___ exp.time_ 3 omega 43.00 95.00 1.0000 2.5600 omega____ theta____ kappa____ phi______ frames - 18.8601 178.0000 -90.0000 52 #__ type_ start__ end____ width___ exp.time_ 4 omega -6.00 51.00 1.0000 2.5600 omega____ theta____ kappa____ phi______ frames - 18.8601 77.0000 -90.0000 57 #__ type_ start__ end____ width___ exp.time_ 5 omega -60.00 -35.00 1.0000 2.5600 omega____ theta____ kappa____ phi______ frames - -17.7663 -178.0000 30.0000 25 ; _diffrn_measurement_method '\w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'CrysAlisPro, Agilent Technologies,' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies,' _computing_data_reduction 'CrysAlisPro, Agilent Technologies,' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'Ortep3 v. 2.02 (LJ Farrugia, 1997)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 16540 _reflns_number_total 7251 _diffrn_reflns_av_R_equivalents 0.031 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 7251 # Theoretical number of reflections is about 16633 _diffrn_reflns_theta_min 3.314 _diffrn_reflns_theta_max 29.080 _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 26.467 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -19 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 2.78 _oxford_diffrn_Wilson_scale 0.10 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.70 _refine_diff_density_max 0.60 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 7238 _refine_ls_number_restraints 0 _refine_ls_number_parameters 469 _oxford_refine_ls_R_factor_ref 0.0714 _refine_ls_wR_factor_ref 0.1035 _refine_ls_goodness_of_fit_ref 0.9732 _refine_ls_shift/su_max 0.0008276 _refine_ls_shift/su_mean 0.0000397 # The values computed with all filters except I/sigma _oxford_reflns_number_all 7238 _refine_ls_R_factor_all 0.0714 _refine_ls_wR_factor_all 0.1035 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5341 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_gt 0.0916 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 3.05P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens B1 B 0.78718(16) 0.1744(3) 0.58133(13) 0.0216 1.0000 Uani . . . . . . Cl1 Cl 0.39835(4) 0.12914(6) 0.72202(3) 0.0333 1.0000 Uani . . . . . . Cl2 Cl 0.20223(4) 0.17108(6) 0.62295(3) 0.0361 1.0000 Uani . . . . . . N1 N 0.27285(12) 0.15780(18) 0.81406(10) 0.0243 1.0000 Uani . . . . . . N2 N 0.15297(12) 0.18217(18) 0.75307(10) 0.0243 1.0000 Uani . . . . . . F1 F 0.89343(10) 0.07549(15) 0.47208(7) 0.0389 1.0000 Uani . . . . . . F2 F 0.99583(10) 0.20724(18) 0.38977(8) 0.0518 1.0000 Uani . . . . . . F3 F 0.99295(10) 0.46768(18) 0.38849(8) 0.0531 1.0000 Uani . . . . . . F4 F 0.89004(10) 0.59643(15) 0.47865(8) 0.0479 1.0000 Uani . . . . . . F5 F 0.79989(9) 0.46955(13) 0.56870(7) 0.0336 1.0000 Uani . . . . . . F6 F 0.90335(8) 0.32204(13) 0.66855(7) 0.0266 1.0000 Uani . . . . . . F7 F 0.87703(9) 0.40182(13) 0.79489(7) 0.0328 1.0000 Uani . . . . . . F8 F 0.71547(10) 0.38094(15) 0.84887(7) 0.0389 1.0000 Uani . . . . . . F9 F 0.57866(9) 0.28834(14) 0.76957(8) 0.0355 1.0000 Uani . . . . . . F10 F 0.60259(8) 0.20835(13) 0.64371(7) 0.0276 1.0000 Uani . . . . . . F11 F 0.74747(9) -0.10177(13) 0.53404(7) 0.0337 1.0000 Uani . . . . . . F12 F 0.61318(10) -0.17274(15) 0.45356(8) 0.0446 1.0000 Uani . . . . . . F13 F 0.49823(10) 0.00544(17) 0.40013(7) 0.0478 1.0000 Uani . . . . . . F14 F 0.51732(9) 0.25622(16) 0.43562(8) 0.0463 1.0000 Uani . . . . . . F15 F 0.64927(9) 0.33101(13) 0.51970(8) 0.0356 1.0000 Uani . . . . . . C1 C 0.84315(14) 0.2641(2) 0.52765(11) 0.0240 1.0000 Uani . . . . . . C2 C 0.89261(15) 0.2049(3) 0.47786(12) 0.0298 1.0000 Uani . . . . . . C3 C 0.94405(16) 0.2710(3) 0.43306(12) 0.0355 1.0000 Uani . . . . . . C4 C 0.94325(16) 0.4018(3) 0.43256(12) 0.0360 1.0000 Uani . . . . . . C5 C 0.89275(16) 0.4671(2) 0.47804(13) 0.0336 1.0000 Uani . . . . . . C6 C 0.84563(15) 0.3968(2) 0.52450(12) 0.0267 1.0000 Uani . . . . . . C7 C 0.75541(14) 0.2565(2) 0.64885(11) 0.0205 1.0000 Uani . . . . . . C8 C 0.82046(13) 0.3118(2) 0.69115(11) 0.0204 1.0000 Uani . . . . . . C9 C 0.80897(15) 0.3534(2) 0.75690(12) 0.0237 1.0000 Uani . . . . . . C10 C 0.72715(16) 0.3443(2) 0.78410(12) 0.0267 1.0000 Uani . . . . . . C11 C 0.65903(14) 0.2974(2) 0.74394(12) 0.0244 1.0000 Uani . . . . . . C12 C 0.67400(14) 0.2565(2) 0.67807(12) 0.0218 1.0000 Uani . . . . . . C13 C 0.70492(14) 0.1190(2) 0.53273(11) 0.0236 1.0000 Uani . . . . . . C14 C 0.69206(15) -0.0073(2) 0.51217(12) 0.0260 1.0000 Uani . . . . . . C15 C 0.62314(16) -0.0470(3) 0.46909(12) 0.0312 1.0000 Uani . . . . . . C16 C 0.56500(15) 0.0417(3) 0.44289(12) 0.0333 1.0000 Uani . . . . . . C17 C 0.57442(15) 0.1685(3) 0.46091(12) 0.0309 1.0000 Uani . . . . . . C18 C 0.64328(15) 0.2039(2) 0.50420(12) 0.0266 1.0000 Uani . . . . . . C19 C 0.85400(14) 0.0661(2) 0.61449(12) 0.0246 1.0000 Uani . . . . . . C20 C 0.85154(15) 0.0004(2) 0.67311(12) 0.0263 1.0000 Uani . . . . . . C21 C 0.77899(15) -0.0085(2) 0.72133(12) 0.0243 1.0000 Uani . . . . . . C22 C 0.79536(16) 0.0031(2) 0.79166(13) 0.0319 1.0000 Uani . . . . . . C23 C 0.72866(17) -0.0055(2) 0.83751(13) 0.0343 1.0000 Uani . . . . . . C24 C 0.64255(16) -0.0292(2) 0.81541(12) 0.0286 1.0000 Uani . . . . . . C25 C 0.62579(15) -0.0422(2) 0.74572(12) 0.0262 1.0000 Uani . . . . . . C26 C 0.69250(15) -0.0320(2) 0.69951(12) 0.0249 1.0000 Uani . . . . . . C27 C 0.57018(18) -0.0422(3) 0.86543(14) 0.0388 1.0000 Uani . . . . . . C28 C 0.33466(16) 0.1477(3) 0.87326(13) 0.0356 1.0000 Uani . . . . . . C29 C 0.18689(15) 0.1759(2) 0.81626(12) 0.0265 1.0000 Uani . . . . . . C30 C 0.06043(15) 0.2038(3) 0.73331(13) 0.0350 1.0000 Uani . . . . . . C31 C 0.21989(15) 0.1686(2) 0.70838(12) 0.0239 1.0000 Uani . . . . . . C32 C 0.29492(14) 0.1525(2) 0.74652(12) 0.0243 1.0000 Uani . . . . . . H191 H 0.9064 0.0518 0.5901 0.0288 1.0000 Uiso R . . . . . H201 H 0.9030 -0.0461 0.6867 0.0309 1.0000 Uiso R . . . . . H221 H 0.8537 0.0155 0.8071 0.0384 1.0000 Uiso R . . . . . H231 H 0.7409 0.0046 0.8842 0.0409 1.0000 Uiso R . . . . . H251 H 0.5686 -0.0583 0.7289 0.0316 1.0000 Uiso R . . . . . H261 H 0.6794 -0.0393 0.6531 0.0291 1.0000 Uiso R . . . . . H272 H 0.5434 -0.1224 0.8629 0.0595 1.0000 Uiso R . . . . . H271 H 0.5912 -0.0314 0.9110 0.0599 1.0000 Uiso R . . . . . H273 H 0.5265 0.0201 0.8572 0.0607 1.0000 Uiso R . . . . . H282 H 0.3829 0.2045 0.8654 0.0525 1.0000 Uiso R . . . . . H283 H 0.3049 0.1723 0.9138 0.0526 1.0000 Uiso R . . . . . H281 H 0.3558 0.0600 0.8773 0.0529 1.0000 Uiso R . . . . . H291 H 0.1552 0.1834 0.8567 0.0319 1.0000 Uiso R . . . . . H302 H 0.0398 0.1330 0.7065 0.0515 1.0000 Uiso R . . . . . H303 H 0.0571 0.2821 0.7065 0.0527 1.0000 Uiso R . . . . . H301 H 0.0280 0.2104 0.7736 0.0521 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 B1 0.0170(12) 0.0248(13) 0.0229(13) -0.0017(11) -0.0003(10) -0.0021(10) Cl1 0.0200(3) 0.0335(3) 0.0467(4) -0.0014(3) 0.0060(2) 0.0010(2) Cl2 0.0383(4) 0.0438(4) 0.0260(3) -0.0011(3) -0.0007(3) 0.0056(3) N1 0.0198(10) 0.0237(10) 0.0292(11) 0.0011(8) -0.0029(8) -0.0011(8) N2 0.0177(9) 0.0263(10) 0.0288(11) -0.0012(8) -0.0011(8) 0.0017(8) F1 0.0396(9) 0.0420(9) 0.0359(9) -0.0126(7) 0.0104(7) -0.0044(7) F2 0.0382(9) 0.0861(13) 0.0321(9) -0.0143(9) 0.0147(7) -0.0134(9) F3 0.0411(9) 0.0838(13) 0.0343(9) 0.0180(9) -0.0013(7) -0.0300(9) F4 0.0430(10) 0.0410(9) 0.0584(11) 0.0220(8) -0.0148(8) -0.0148(7) F5 0.0326(8) 0.0258(7) 0.0423(9) 0.0035(6) -0.0008(6) 0.0008(6) F6 0.0149(6) 0.0359(8) 0.0290(7) -0.0016(6) -0.0001(5) -0.0029(5) F7 0.0309(8) 0.0379(8) 0.0289(8) -0.0070(6) -0.0086(6) -0.0015(6) F8 0.0455(9) 0.0444(9) 0.0274(8) -0.0083(7) 0.0095(7) -0.0004(7) F9 0.0237(7) 0.0386(9) 0.0452(9) -0.0057(7) 0.0155(6) -0.0009(6) F10 0.0149(6) 0.0324(8) 0.0355(8) -0.0036(6) 0.0001(5) -0.0023(5) F11 0.0371(8) 0.0283(8) 0.0358(8) -0.0057(6) 0.0025(6) -0.0012(6) F12 0.0479(10) 0.0454(10) 0.0408(9) -0.0174(8) 0.0077(7) -0.0203(7) F13 0.0309(8) 0.0840(13) 0.0282(8) -0.0097(8) -0.0036(6) -0.0228(8) F14 0.0282(8) 0.0656(11) 0.0442(10) 0.0156(8) -0.0124(7) -0.0027(7) F15 0.0298(8) 0.0317(8) 0.0445(9) 0.0051(7) -0.0089(6) 0.0012(6) C1 0.0183(11) 0.0319(13) 0.0217(12) 0.0014(10) -0.0021(9) -0.0044(9) C2 0.0229(12) 0.0411(15) 0.0255(13) -0.0009(11) -0.0001(9) -0.0063(11) C3 0.0255(13) 0.0599(19) 0.0214(13) -0.0066(12) 0.0024(10) -0.0103(12) C4 0.0258(13) 0.0602(19) 0.0217(13) 0.0108(12) -0.0026(10) -0.0154(12) C5 0.0289(13) 0.0342(14) 0.0366(15) 0.0127(12) -0.0135(11) -0.0136(11) C6 0.0206(11) 0.0334(14) 0.0258(13) 0.0024(10) -0.0037(9) -0.0016(10) C7 0.0196(11) 0.0184(11) 0.0233(12) 0.0020(9) -0.0004(9) -0.0003(8) C8 0.0152(10) 0.0209(11) 0.0250(12) 0.0034(9) 0.0004(8) 0.0017(8) C9 0.0250(12) 0.0221(12) 0.0235(12) -0.0014(9) -0.0049(9) 0.0001(9) C10 0.0334(13) 0.0245(12) 0.0226(12) -0.0033(10) 0.0052(10) 0.0032(10) C11 0.0201(11) 0.0202(12) 0.0334(13) 0.0005(10) 0.0081(9) 0.0014(9) C12 0.0166(11) 0.0179(11) 0.0308(13) 0.0003(9) -0.0016(9) 0.0002(8) C13 0.0212(11) 0.0321(13) 0.0176(11) -0.0018(10) 0.0024(9) -0.0041(9) C14 0.0248(12) 0.0330(14) 0.0204(12) -0.0013(10) 0.0059(9) -0.0039(10) C15 0.0305(13) 0.0394(15) 0.0241(13) -0.0094(11) 0.0078(10) -0.0141(11) C16 0.0225(12) 0.0584(18) 0.0191(12) -0.0057(12) 0.0017(9) -0.0163(12) C17 0.0202(12) 0.0490(16) 0.0235(13) 0.0089(11) -0.0016(9) -0.0033(11) C18 0.0222(12) 0.0306(13) 0.0270(13) 0.0018(10) 0.0014(9) -0.0053(10) C19 0.0185(11) 0.0250(12) 0.0303(13) -0.0066(10) 0.0032(9) -0.0013(9) C20 0.0197(11) 0.0247(12) 0.0343(14) -0.0010(10) -0.0026(10) 0.0025(9) C21 0.0268(12) 0.0172(11) 0.0289(13) 0.0008(9) -0.0006(9) 0.0028(9) C22 0.0261(13) 0.0366(15) 0.0325(14) -0.0028(11) -0.0053(10) 0.0004(11) C23 0.0411(15) 0.0372(15) 0.0242(13) -0.0019(11) -0.0031(11) 0.0026(12) C24 0.0327(13) 0.0231(12) 0.0302(14) 0.0037(10) 0.0038(10) 0.0023(10) C25 0.0243(12) 0.0210(12) 0.0334(14) 0.0017(10) 0.0009(10) -0.0004(9) C26 0.0267(12) 0.0233(12) 0.0242(12) 0.0008(10) -0.0038(9) 0.0002(9) C27 0.0409(16) 0.0381(15) 0.0382(16) 0.0010(12) 0.0111(12) 0.0029(12) C28 0.0300(14) 0.0394(15) 0.0364(15) 0.0012(12) -0.0098(11) -0.0020(11) C29 0.0243(12) 0.0265(13) 0.0289(13) 0.0007(10) 0.0019(10) -0.0013(10) C30 0.0180(12) 0.0489(17) 0.0378(15) -0.0026(12) -0.0032(10) 0.0044(11) C31 0.0226(12) 0.0221(12) 0.0271(13) -0.0012(10) 0.0015(9) 0.0018(9) C32 0.0200(11) 0.0212(12) 0.0319(13) -0.0005(10) 0.0034(9) -0.0011(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.08(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 B1 . C1 . 1.664(3) yes B1 . C7 . 1.661(3) yes B1 . C13 . 1.651(3) yes B1 . C19 . 1.637(3) yes Cl1 . C32 . 1.684(2) yes Cl2 . C31 . 1.685(2) yes N1 . C28 . 1.471(3) yes N1 . C29 . 1.328(3) yes N1 . C32 . 1.378(3) yes N2 . C29 . 1.326(3) yes N2 . C30 . 1.468(3) yes N2 . C31 . 1.377(3) yes F1 . C2 . 1.350(3) yes F2 . C3 . 1.354(3) yes F3 . C4 . 1.356(3) yes F4 . C5 . 1.345(3) yes F5 . C6 . 1.361(3) yes F6 . C8 . 1.360(2) yes F7 . C9 . 1.352(2) yes F8 . C10 . 1.343(3) yes F9 . C11 . 1.346(2) yes F10 . C12 . 1.356(2) yes F11 . C14 . 1.355(3) yes F12 . C15 . 1.349(3) yes F13 . C16 . 1.349(3) yes F14 . C17 . 1.343(3) yes F15 . C18 . 1.357(3) yes C1 . C2 . 1.397(3) yes C1 . C6 . 1.381(3) yes C2 . C3 . 1.382(3) yes C3 . C4 . 1.358(4) yes C4 . C5 . 1.378(4) yes C5 . C6 . 1.388(3) yes C7 . C8 . 1.394(3) yes C7 . C12 . 1.387(3) yes C8 . C9 . 1.376(3) yes C9 . C10 . 1.379(3) yes C10 . C11 . 1.370(3) yes C11 . C12 . 1.385(3) yes C13 . C14 . 1.385(3) yes C13 . C18 . 1.392(3) yes C14 . C15 . 1.387(3) yes C15 . C16 . 1.366(4) yes C16 . C17 . 1.370(4) yes C17 . C18 . 1.376(3) yes C19 . C20 . 1.337(3) yes C19 . H191 . 0.959 no C20 . C21 . 1.485(3) yes C20 . H201 . 0.952 no C21 . C22 . 1.396(3) yes C21 . C26 . 1.394(3) yes C22 . C23 . 1.385(3) yes C22 . H221 . 0.939 no C23 . C24 . 1.391(3) yes C23 . H231 . 0.932 no C24 . C25 . 1.386(3) yes C24 . C27 . 1.509(3) yes C25 . C26 . 1.391(3) yes C25 . H251 . 0.936 no C26 . H261 . 0.926 no C27 . H272 . 0.929 no C27 . H271 . 0.943 no C27 . H273 . 0.938 no C28 . H282 . 0.961 no C28 . H283 . 0.965 no C28 . H281 . 0.969 no C29 . H291 . 0.947 no C30 . H302 . 0.951 no C30 . H303 . 0.969 no C30 . H301 . 0.950 no C31 . C32 . 1.355(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . B1 . C7 . 112.81(18) yes C1 . B1 . C13 . 103.18(17) yes C7 . B1 . C13 . 113.57(18) yes C1 . B1 . C19 . 107.97(18) yes C7 . B1 . C19 . 103.46(18) yes C13 . B1 . C19 . 116.02(19) yes C28 . N1 . C29 . 126.2(2) yes C28 . N1 . C32 . 125.5(2) yes C29 . N1 . C32 . 108.28(19) yes C29 . N2 . C30 . 126.3(2) yes C29 . N2 . C31 . 108.39(19) yes C30 . N2 . C31 . 125.3(2) yes B1 . C1 . C2 . 119.9(2) yes B1 . C1 . C6 . 127.1(2) yes C2 . C1 . C6 . 113.0(2) yes C1 . C2 . F1 . 120.2(2) yes C1 . C2 . C3 . 124.0(2) yes F1 . C2 . C3 . 115.8(2) yes F2 . C3 . C2 . 120.9(3) yes F2 . C3 . C4 . 119.4(2) yes C2 . C3 . C4 . 119.8(2) yes F3 . C4 . C3 . 120.3(3) yes F3 . C4 . C5 . 120.2(3) yes C3 . C4 . C5 . 119.5(2) yes F4 . C5 . C4 . 121.0(2) yes F4 . C5 . C6 . 120.2(2) yes C4 . C5 . C6 . 118.7(2) yes F5 . C6 . C5 . 114.5(2) yes F5 . C6 . C1 . 120.7(2) yes C5 . C6 . C1 . 124.8(2) yes B1 . C7 . C8 . 117.56(19) yes B1 . C7 . C12 . 128.39(19) yes C8 . C7 . C12 . 112.6(2) yes F6 . C8 . C7 . 119.32(19) yes F6 . C8 . C9 . 115.62(19) yes C7 . C8 . C9 . 125.0(2) yes F7 . C9 . C8 . 120.7(2) yes F7 . C9 . C10 . 120.1(2) yes C8 . C9 . C10 . 119.3(2) yes F8 . C10 . C9 . 120.0(2) yes F8 . C10 . C11 . 121.3(2) yes C9 . C10 . C11 . 118.8(2) yes F9 . C11 . C10 . 119.6(2) yes F9 . C11 . C12 . 120.7(2) yes C10 . C11 . C12 . 119.7(2) yes F10 . C12 . C7 . 120.7(2) yes F10 . C12 . C11 . 114.74(19) yes C7 . C12 . C11 . 124.4(2) yes B1 . C13 . C14 . 126.5(2) yes B1 . C13 . C18 . 119.9(2) yes C14 . C13 . C18 . 113.4(2) yes F11 . C14 . C13 . 121.0(2) yes F11 . C14 . C15 . 115.3(2) yes C13 . C14 . C15 . 123.7(2) yes F12 . C15 . C14 . 120.1(2) yes F12 . C15 . C16 . 120.2(2) yes C14 . C15 . C16 . 119.7(2) yes F13 . C16 . C15 . 120.7(2) yes F13 . C16 . C17 . 119.9(2) yes C15 . C16 . C17 . 119.4(2) yes F14 . C17 . C16 . 119.8(2) yes F14 . C17 . C18 . 121.1(2) yes C16 . C17 . C18 . 119.1(2) yes F15 . C18 . C13 . 119.2(2) yes F15 . C18 . C17 . 116.2(2) yes C13 . C18 . C17 . 124.6(2) yes B1 . C19 . C20 . 130.9(2) yes B1 . C19 . H191 . 115.3 no C20 . C19 . H191 . 113.5 no C19 . C20 . C21 . 128.5(2) yes C19 . C20 . H201 . 116.8 no C21 . C20 . H201 . 114.7 no C20 . C21 . C22 . 120.8(2) yes C20 . C21 . C26 . 122.4(2) yes C22 . C21 . C26 . 116.8(2) yes C21 . C22 . C23 . 121.7(2) yes C21 . C22 . H221 . 117.5 no C23 . C22 . H221 . 120.8 no C22 . C23 . C24 . 121.2(2) yes C22 . C23 . H231 . 120.2 no C24 . C23 . H231 . 118.6 no C23 . C24 . C25 . 117.5(2) yes C23 . C24 . C27 . 121.3(2) yes C25 . C24 . C27 . 121.2(2) yes C24 . C25 . C26 . 121.4(2) yes C24 . C25 . H251 . 120.0 no C26 . C25 . H251 . 118.6 no C21 . C26 . C25 . 121.4(2) yes C21 . C26 . H261 . 118.9 no C25 . C26 . H261 . 119.7 no C24 . C27 . H272 . 112.2 no C24 . C27 . H271 . 111.8 no H272 . C27 . H271 . 106.9 no C24 . C27 . H273 . 111.1 no H272 . C27 . H273 . 107.5 no H271 . C27 . H273 . 107.2 no N1 . C28 . H282 . 107.7 no N1 . C28 . H283 . 108.8 no H282 . C28 . H283 . 110.8 no N1 . C28 . H281 . 109.5 no H282 . C28 . H281 . 109.6 no H283 . C28 . H281 . 110.3 no N1 . C29 . N2 . 109.2(2) yes N1 . C29 . H291 . 125.1 no N2 . C29 . H291 . 125.7 no N2 . C30 . H302 . 108.9 no N2 . C30 . H303 . 107.6 no H302 . C30 . H303 . 109.9 no N2 . C30 . H301 . 108.5 no H302 . C30 . H301 . 110.1 no H303 . C30 . H301 . 111.8 no N2 . C31 . Cl2 . 122.32(17) yes N2 . C31 . C32 . 107.1(2) yes Cl2 . C31 . C32 . 130.58(18) yes N1 . C32 . Cl1 . 122.96(17) yes N1 . C32 . C31 . 107.03(19) yes Cl1 . C32 . C31 . 130.01(19) yes _iucr_refine_instructions_details_constraints ; # # Punched on 16/03/15 at 11:19:52 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 272,X'S) H ( 271,X'S) H ( 273,X'S) RIDE C ( 28,X'S) H ( 282,X'S) H ( 283,X'S) H ( 281,X'S) RIDE C ( 29,X'S) H ( 291,X'S) RIDE C ( 30,X'S) H ( 302,X'S) H ( 303,X'S) H ( 301,X'S) END ; _iucr_refine_instructions_details_restraints ; # # Punched on 16/03/15 at 11:19:52 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _chemical_name_systematic '[1,3-Me2-4,5-Cl2-imidazolium][B((C6F5)3)-Z-(2-methylstyrene)]' _chemical_properties_physical Moisture-sensitive