# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2-X-ray #============================================================================== _audit_creation_date 12-08-15 _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title 6449 _chemical_name_systematic . _chemical_melting_point 'not measured' _refine_special_details ; The hydrogen atoms were refined with soft distance and ADP restraints prior to inclusion in the final refinement with a riding model. The exception was B(11) (bound to boron) which was unrestrained, however, free refinement of the isotropic displacement parameter was unstable, so this was restrained to a sensible value. ; _cell_length_a 14.0366(2) _cell_length_b 17.3755(2) _cell_length_c 13.3392(2) _cell_angle_alpha 90 _cell_angle_beta 114.9580(17) _cell_angle_gamma 90 _cell_volume 2949.53(8) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc' 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 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 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' B 0.0090 0.0039 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' Cl 0.3639 0.7018 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 0.0727 0.0534 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 = C24 H12 B1 Cl5 F10 N1 # Dc = 1.56 Fooo = 1480.00 Mu = 52.29 M = 692.42 # Found Formula = C27 H21 B1 Cl5 F10 N1 # Dc = 1.66 FOOO = 1480.00 Mu = 52.67 M = 737.52 _chemical_formula_sum 'C27 H21 B1 Cl5 F10 N1' _chemical_formula_moiety 'C18 H B Cl5 F10, C9 H20 N' _chemical_compound_source . _chemical_formula_weight 737.52 _cell_measurement_reflns_used 38049 _cell_measurement_theta_min 3 _cell_measurement_theta_max 77 _cell_measurement_temperature 100 _exptl_crystal_description plate _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.661 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 5.267 # Sheldrick geometric approximatio 0.39 0.77 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.77 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _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 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 100 _diffrn_reflns_number 64857 _reflns_number_total 6196 _diffrn_reflns_av_R_equivalents 0.029 # Number of reflections with Friedels Law is 6196 # Theoretical number of reflections is about 12458 _diffrn_reflns_theta_min 3.473 _diffrn_reflns_theta_max 76.899 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 75.361 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -17 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 1.87 _oxford_diffrn_Wilson_scale 0.10 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.33 _refine_diff_density_max 0.68 # 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 6171 _refine_ls_number_restraints 0 _refine_ls_number_parameters 397 _oxford_refine_ls_R_factor_ref 0.0270 _refine_ls_wR_factor_ref 0.0668 _refine_ls_goodness_of_fit_ref 1.0133 _refine_ls_shift/su_max 0.0009615 _refine_ls_shift/su_mean 0.0001776 # The values computed with all filters except I/sigma _oxford_reflns_number_all 6171 _refine_ls_R_factor_all 0.0270 _refine_ls_wR_factor_all 0.0668 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5942 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_gt 0.0661 # 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^ + 1.72P] ,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 0.72855(11) 0.46001(8) 0.35657(11) 0.0157 1.0000 Uani . . . . . . C1 C 0.77268(9) 0.42885(7) 0.26800(10) 0.0159 1.0000 Uani . . . . . . C2 C 0.73326(9) 0.36141(7) 0.20714(10) 0.0153 1.0000 Uani . . . . . . C3 C 0.74937(10) 0.34094(7) 0.11458(10) 0.0171 1.0000 Uani . . . . . . C4 C 0.81876(10) 0.38386(8) 0.08728(10) 0.0191 1.0000 Uani . . . . . . C5 C 0.86769(10) 0.44789(8) 0.15113(11) 0.0207 1.0000 Uani . . . . . . C6 C 0.84230(10) 0.46974(8) 0.23787(10) 0.0200 1.0000 Uani . . . . . . C7 C 0.77911(9) 0.41729(7) 0.47671(10) 0.0160 1.0000 Uani . . . . . . C8 C 0.8591(1) 0.36268(7) 0.51086(10) 0.0169 1.0000 Uani . . . . . . C9 C 0.90412(9) 0.33178(7) 0.61632(10) 0.0184 1.0000 Uani . . . . . . C10 C 0.87072(10) 0.35505(8) 0.69462(10) 0.0205 1.0000 Uani . . . . . . C11 C 0.79225(11) 0.40961(8) 0.66608(11) 0.0215 1.0000 Uani . . . . . . C12 C 0.74989(10) 0.43871(7) 0.56016(10) 0.0180 1.0000 Uani . . . . . . C13 C 0.59929(10) 0.45979(7) 0.29106(10) 0.0162 1.0000 Uani . . . . . . C14 C 0.52642(10) 0.42025(7) 0.31659(10) 0.0173 1.0000 Uani . . . . . . C15 C 0.41874(10) 0.42555(8) 0.25634(11) 0.0206 1.0000 Uani . . . . . . C16 C 0.37753(10) 0.46935(8) 0.16131(11) 0.0238 1.0000 Uani . . . . . . C17 C 0.44587(11) 0.50891(8) 0.13023(11) 0.0237 1.0000 Uani . . . . . . C18 C 0.55295(11) 0.50420(7) 0.19558(10) 0.0195 1.0000 Uani . . . . . . Cl1 Cl 0.90420(3) 0.55122(2) 0.31246(3) 0.0390 1.0000 Uani . . . . . . Cl2 Cl 0.95654(3) 0.49983(2) 0.12030(3) 0.0311 1.0000 Uani . . . . . . Cl3 Cl 0.84262(3) 0.35827(2) -0.02411(3) 0.0276 1.0000 Uani . . . . . . Cl4 Cl 0.67997(2) 0.266145(18) 0.03055(2) 0.0225 1.0000 Uani . . . . . . Cl5 Cl 0.66355(2) 0.297556(16) 0.25128(2) 0.0186 1.0000 Uani . . . . . . F1 F 0.89830(6) 0.33663(5) 0.44051(6) 0.0231 1.0000 Uani . . . . . . F2 F 0.98134(6) 0.27899(5) 0.64375(6) 0.0243 1.0000 Uani . . . . . . F3 F 0.91390(7) 0.32471(5) 0.79668(6) 0.0292 1.0000 Uani . . . . . . F4 F 0.75744(8) 0.43363(5) 0.74038(7) 0.0330 1.0000 Uani . . . . . . F5 F 0.67313(6) 0.49297(4) 0.53820(6) 0.0229 1.0000 Uani . . . . . . F6 F 0.55866(6) 0.37147(4) 0.40378(6) 0.0206 1.0000 Uani . . . . . . F7 F 0.35273(6) 0.38640(5) 0.28851(7) 0.0268 1.0000 Uani . . . . . . F8 F 0.27352(6) 0.47226(5) 0.09992(7) 0.0325 1.0000 Uani . . . . . . F9 F 0.40875(7) 0.55195(5) 0.03819(7) 0.0339 1.0000 Uani . . . . . . F10 F 0.61438(7) 0.54693(5) 0.16160(7) 0.0258 1.0000 Uani . . . . . . N30 N 0.71225(8) 0.65000(6) 0.49398(9) 0.0196 1.0000 Uani . . . . . . C41 C 0.81652(11) 0.69248(8) 0.55709(12) 0.0256 1.0000 Uani . . . . . . C42 C 0.79462(11) 0.75841(9) 0.62031(13) 0.0286 1.0000 Uani . . . . . . C43 C 0.70307(11) 0.80896(8) 0.54653(13) 0.0276 1.0000 Uani . . . . . . C44 C 0.60249(11) 0.76134(8) 0.49333(12) 0.0239 1.0000 Uani . . . . . . C45 C 0.61102(10) 0.69397(7) 0.42350(11) 0.0190 1.0000 Uani . . . . . . C46 C 0.86123(12) 0.72041(10) 0.47730(15) 0.0339 1.0000 Uani . . . . . . C47 C 0.88989(13) 0.63261(10) 0.63571(16) 0.0402 1.0000 Uani . . . . . . C48 C 0.52189(11) 0.63655(8) 0.39969(12) 0.0231 1.0000 Uani . . . . . . C49 C 0.61314(12) 0.71910(9) 0.31492(12) 0.0266 1.0000 Uani . . . . . . H11 H 0.7547 0.5351 0.3782 0.0180 1.0000 Uiso R . . . . . H301 H 0.6992 0.6240 0.5436 0.0289 1.0000 Uiso R . . . . . H302 H 0.7235 0.6137 0.4523 0.0292 1.0000 Uiso R . . . . . H493 H 0.5431 0.7346 0.2649 0.0396 1.0000 Uiso R . . . . . H492 H 0.6336 0.6774 0.2816 0.0395 1.0000 Uiso R . . . . . H491 H 0.6606 0.7621 0.3248 0.0396 1.0000 Uiso R . . . . . H421 H 0.7794 0.7371 0.6793 0.0336 1.0000 Uiso R . . . . . H422 H 0.8580 0.7893 0.6534 0.0347 1.0000 Uiso R . . . . . H431 H 0.6912 0.8494 0.5902 0.0340 1.0000 Uiso R . . . . . H432 H 0.7193 0.8323 0.4899 0.0322 1.0000 Uiso R . . . . . H441 H 0.5844 0.7401 0.5514 0.0290 1.0000 Uiso R . . . . . H442 H 0.5438 0.7941 0.4451 0.0289 1.0000 Uiso R . . . . . H463 H 0.9337 0.7359 0.5202 0.0507 1.0000 Uiso R . . . . . H462 H 0.8603 0.6799 0.4274 0.0504 1.0000 Uiso R . . . . . H461 H 0.8212 0.7644 0.4340 0.0504 1.0000 Uiso R . . . . . H471 H 0.9549 0.6570 0.6805 0.0588 1.0000 Uiso R . . . . . H472 H 0.8611 0.6124 0.6842 0.0573 1.0000 Uiso R . . . . . H473 H 0.9010 0.5903 0.5943 0.0582 1.0000 Uiso R . . . . . H483 H 0.5251 0.6151 0.4684 0.0340 1.0000 Uiso R . . . . . H482 H 0.5272 0.5947 0.3556 0.0341 1.0000 Uiso R . . . . . H481 H 0.4553 0.6621 0.3626 0.0346 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 0.0188(6) 0.0169(6) 0.0135(6) -0.0009(5) 0.0088(5) -0.0015(5) C1 0.0172(5) 0.0184(6) 0.0118(5) 0.0009(4) 0.0059(4) -0.0004(4) C2 0.0152(5) 0.0170(6) 0.0140(5) 0.0015(4) 0.0066(4) 0.0004(4) C3 0.0179(6) 0.0168(6) 0.0139(5) -0.0007(4) 0.0042(5) 0.0036(4) C4 0.0216(6) 0.0252(6) 0.0123(5) 0.0037(5) 0.0090(5) 0.0067(5) C5 0.0196(6) 0.0279(7) 0.0170(6) 0.0041(5) 0.0101(5) -0.0011(5) C6 0.0218(6) 0.0225(6) 0.0167(6) -0.0023(5) 0.0091(5) -0.0062(5) C7 0.0171(5) 0.0177(6) 0.0140(5) -0.0009(4) 0.0074(4) -0.0038(4) C8 0.0160(5) 0.0228(6) 0.0142(5) -0.0020(4) 0.0085(5) -0.0025(5) C9 0.0141(5) 0.0213(6) 0.0179(6) 0.0000(5) 0.0051(5) -0.0002(5) C10 0.0236(6) 0.0247(6) 0.0107(5) 0.0026(5) 0.0047(5) -0.0008(5) C11 0.0301(7) 0.0235(6) 0.0147(6) -0.0015(5) 0.0132(5) 0.0007(5) C12 0.0223(6) 0.0158(6) 0.0174(6) 0.0000(4) 0.0098(5) 0.0011(5) C13 0.0212(6) 0.0142(5) 0.0148(5) -0.0009(4) 0.0090(5) 0.0022(4) C14 0.0214(6) 0.0155(6) 0.0161(5) 0.0014(4) 0.0089(5) 0.0041(5) C15 0.0200(6) 0.0190(6) 0.0249(6) -0.0043(5) 0.0114(5) 0.0008(5) C16 0.0198(6) 0.0244(6) 0.0217(6) -0.0054(5) 0.0035(5) 0.0074(5) C17 0.0315(7) 0.0211(6) 0.0151(6) 0.0022(5) 0.0065(5) 0.0097(5) C18 0.0274(6) 0.0162(6) 0.0171(6) 0.0004(5) 0.0115(5) 0.0021(5) Cl1 0.0502(2) 0.0402(2) 0.0386(2) -0.02042(16) 0.03050(18) -0.03091(18) Cl2 0.03065(17) 0.0430(2) 0.02731(17) 0.00188(14) 0.01967(14) -0.01036(14) Cl3 0.03848(18) 0.03276(18) 0.01875(15) 0.00203(12) 0.01918(14) 0.00750(14) Cl4 0.02513(15) 0.02047(15) 0.02013(14) -0.00727(11) 0.00795(12) 0.00147(11) Cl5 0.02059(14) 0.01573(13) 0.02207(14) -0.00146(10) 0.01162(11) -0.00313(10) F1 0.0204(4) 0.0346(4) 0.0178(4) 0.0020(3) 0.0116(3) 0.0067(3) F2 0.0190(4) 0.0314(4) 0.0202(4) 0.0040(3) 0.0062(3) 0.0072(3) F3 0.0365(5) 0.0368(5) 0.0133(4) 0.0070(3) 0.0096(3) 0.0088(4) F4 0.0505(5) 0.0379(5) 0.0184(4) 0.0038(3) 0.0222(4) 0.0148(4) F5 0.0325(4) 0.0205(4) 0.0199(4) 0.0022(3) 0.0153(3) 0.0078(3) F6 0.0214(4) 0.0213(4) 0.0224(4) 0.0071(3) 0.0124(3) 0.0027(3) F7 0.0208(4) 0.0269(4) 0.0369(5) -0.0037(3) 0.0162(3) -0.0018(3) F8 0.0204(4) 0.0380(5) 0.0302(4) -0.0064(4) 0.0020(3) 0.0086(3) F9 0.0403(5) 0.0357(5) 0.0197(4) 0.0099(3) 0.0068(4) 0.0152(4) F10 0.0366(4) 0.0226(4) 0.0222(4) 0.0067(3) 0.0162(3) 0.0006(3) N30 0.0203(5) 0.0178(5) 0.0222(5) 0.0017(4) 0.0104(4) 0.0046(4) C41 0.0181(6) 0.0240(7) 0.0319(7) -0.0019(6) 0.0079(5) 0.0032(5) C42 0.0248(7) 0.0289(7) 0.0289(7) -0.0064(6) 0.0082(6) 0.0006(6) C43 0.0268(7) 0.0211(7) 0.0362(8) -0.0065(6) 0.0146(6) 0.0024(5) C44 0.0222(6) 0.0226(6) 0.0288(7) -0.0033(5) 0.0128(5) 0.0046(5) C45 0.0184(6) 0.0191(6) 0.0210(6) 0.0025(5) 0.0097(5) 0.0058(5) C46 0.0255(7) 0.0327(8) 0.0511(10) -0.0055(7) 0.0236(7) -0.0005(6) C47 0.0267(8) 0.0347(8) 0.0445(10) 0.0028(7) 0.0009(7) 0.0097(6) C48 0.0226(6) 0.0226(6) 0.0260(7) -0.0014(5) 0.0123(5) 0.0017(5) C49 0.0313(7) 0.0280(7) 0.0230(7) 0.0051(5) 0.0140(6) 0.0041(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.164(19) 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 . 1.6402(17) yes B1 . C7 . 1.6319(17) yes B1 . C13 . 1.6485(18) yes B1 . H11 . 1.353 no C1 . C2 . 1.3997(17) yes C1 . C6 . 1.3974(17) yes C2 . C3 . 1.3919(17) yes C2 . Cl5 . 1.7382(12) yes C3 . C4 . 1.3917(18) yes C3 . Cl4 . 1.7243(13) yes C4 . C5 . 1.3933(19) yes C4 . Cl3 . 1.7139(12) yes C5 . C6 . 1.3992(18) yes C5 . Cl2 . 1.7240(13) yes C6 . Cl1 . 1.7377(13) yes C7 . C8 . 1.3913(18) yes C7 . C12 . 1.3897(17) yes C8 . C9 . 1.3843(17) yes C8 . F1 . 1.3510(14) yes C9 . C10 . 1.3738(18) yes C9 . F2 . 1.3474(15) yes C10 . C11 . 1.3795(19) yes C10 . F3 . 1.3425(14) yes C11 . C12 . 1.3771(18) yes C11 . F4 . 1.3431(15) yes C12 . F5 . 1.3673(14) yes C13 . C14 . 1.3886(18) yes C13 . C18 . 1.3934(17) yes C14 . C15 . 1.3834(18) yes C14 . F6 . 1.3533(14) yes C15 . C16 . 1.379(2) yes C15 . F7 . 1.3567(15) yes C16 . C17 . 1.378(2) yes C16 . F8 . 1.3400(15) yes C17 . C18 . 1.3857(19) yes C17 . F9 . 1.3410(15) yes C18 . F10 . 1.3528(15) yes N30 . C41 . 1.5349(17) yes N30 . C45 . 1.5360(15) yes N30 . H301 . 0.882 no N30 . H302 . 0.897 no C41 . C42 . 1.529(2) yes C41 . C46 . 1.525(2) yes C41 . C47 . 1.527(2) yes C42 . C43 . 1.525(2) yes C42 . H421 . 0.971 no C42 . H422 . 0.971 no C43 . C44 . 1.528(2) yes C43 . H431 . 0.971 no C43 . H432 . 0.965 no C44 . C45 . 1.5317(18) yes C44 . H441 . 0.983 no C44 . H442 . 0.984 no C45 . C48 . 1.5252(18) yes C45 . C49 . 1.5250(18) yes C46 . H463 . 0.971 no C46 . H462 . 0.965 no C46 . H461 . 0.980 no C47 . H471 . 0.953 no C47 . H472 . 0.962 no C47 . H473 . 0.972 no C48 . H483 . 0.972 no C48 . H482 . 0.957 no C48 . H481 . 0.962 no C49 . H493 . 0.964 no C49 . H492 . 0.955 no C49 . H491 . 0.972 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 C1 . B1 . C7 . 114.66(10) yes C1 . B1 . C13 . 106.45(9) yes C7 . B1 . C13 . 116.41(10) yes C1 . B1 . H11 . 108.7 no C7 . B1 . H11 . 105.2 no C13 . B1 . H11 . 104.7 no B1 . C1 . C2 . 121.14(10) yes B1 . C1 . C6 . 124.18(11) yes C2 . C1 . C6 . 114.34(11) yes C1 . C2 . C3 . 123.77(11) yes C1 . C2 . Cl5 . 118.63(9) yes C3 . C2 . Cl5 . 117.57(9) yes C2 . C3 . C4 . 119.26(11) yes C2 . C3 . Cl4 . 120.70(10) yes C4 . C3 . Cl4 . 119.97(9) yes C3 . C4 . C5 . 119.12(11) yes C3 . C4 . Cl3 . 120.15(10) yes C5 . C4 . Cl3 . 120.73(10) yes C4 . C5 . C6 . 119.37(12) yes C4 . C5 . Cl2 . 119.46(10) yes C6 . C5 . Cl2 . 121.16(10) yes C5 . C6 . C1 . 123.56(12) yes C5 . C6 . Cl1 . 117.02(10) yes C1 . C6 . Cl1 . 119.41(10) yes B1 . C7 . C8 . 126.04(11) yes B1 . C7 . C12 . 120.78(11) yes C8 . C7 . C12 . 112.97(11) yes C7 . C8 . C9 . 123.84(11) yes C7 . C8 . F1 . 120.66(11) yes C9 . C8 . F1 . 115.50(11) yes C8 . C9 . C10 . 120.15(12) yes C8 . C9 . F2 . 120.69(11) yes C10 . C9 . F2 . 119.16(11) yes C9 . C10 . C11 . 118.77(12) yes C9 . C10 . F3 . 120.17(12) yes C11 . C10 . F3 . 121.06(12) yes C10 . C11 . C12 . 118.96(12) yes C10 . C11 . F4 . 120.44(11) yes C12 . C11 . F4 . 120.59(12) yes C7 . C12 . C11 . 125.30(12) yes C7 . C12 . F5 . 119.04(11) yes C11 . C12 . F5 . 115.66(11) yes B1 . C13 . C14 . 129.12(11) yes B1 . C13 . C18 . 117.91(11) yes C14 . C13 . C18 . 112.97(11) yes C13 . C14 . C15 . 124.19(12) yes C13 . C14 . F6 . 120.45(11) yes C15 . C14 . F6 . 115.35(11) yes C14 . C15 . C16 . 120.16(12) yes C14 . C15 . F7 . 120.49(12) yes C16 . C15 . F7 . 119.33(12) yes C15 . C16 . C17 . 118.45(12) yes C15 . C16 . F8 . 120.58(13) yes C17 . C16 . F8 . 120.96(13) yes C16 . C17 . C18 . 119.29(12) yes C16 . C17 . F9 . 120.17(13) yes C18 . C17 . F9 . 120.53(13) yes C13 . C18 . C17 . 124.86(12) yes C13 . C18 . F10 . 119.51(12) yes C17 . C18 . F10 . 115.63(11) yes C41 . N30 . C45 . 121.22(10) yes C41 . N30 . H301 . 106.7 no C45 . N30 . H301 . 106.4 no C41 . N30 . H302 . 107.5 no C45 . N30 . H302 . 109.3 no H301 . N30 . H302 . 104.6 no N30 . C41 . C42 . 107.20(11) yes N30 . C41 . C46 . 110.38(12) yes C42 . C41 . C46 . 112.61(13) yes N30 . C41 . C47 . 105.06(12) yes C42 . C41 . C47 . 111.47(13) yes C46 . C41 . C47 . 109.83(13) yes C41 . C42 . C43 . 112.74(12) yes C41 . C42 . H421 . 109.0 no C43 . C42 . H421 . 109.2 no C41 . C42 . H422 . 107.8 no C43 . C42 . H422 . 109.6 no H421 . C42 . H422 . 108.4 no C42 . C43 . C44 . 110.47(12) yes C42 . C43 . H431 . 109.9 no C44 . C43 . H431 . 108.1 no C42 . C43 . H432 . 109.5 no C44 . C43 . H432 . 110.0 no H431 . C43 . H432 . 108.8 no C43 . C44 . C45 . 113.72(11) yes C43 . C44 . H441 . 109.4 no C45 . C44 . H441 . 107.7 no C43 . C44 . H442 . 110.2 no C45 . C44 . H442 . 107.6 no H441 . C44 . H442 . 108.0 no N30 . C45 . C44 . 107.30(10) yes N30 . C45 . C48 . 105.53(10) yes C44 . C45 . C48 . 111.03(11) yes N30 . C45 . C49 . 109.87(10) yes C44 . C45 . C49 . 113.37(11) yes C48 . C45 . C49 . 109.42(11) yes C41 . C46 . H463 . 108.3 no C41 . C46 . H462 . 111.1 no H463 . C46 . H462 . 108.3 no C41 . C46 . H461 . 110.9 no H463 . C46 . H461 . 109.2 no H462 . C46 . H461 . 109.0 no C41 . C47 . H471 . 108.5 no C41 . C47 . H472 . 111.0 no H471 . C47 . H472 . 107.6 no C41 . C47 . H473 . 110.4 no H471 . C47 . H473 . 110.6 no H472 . C47 . H473 . 108.7 no C45 . C48 . H483 . 110.3 no C45 . C48 . H482 . 110.8 no H483 . C48 . H482 . 107.7 no C45 . C48 . H481 . 109.8 no H483 . C48 . H481 . 108.0 no H482 . C48 . H481 . 110.2 no C45 . C49 . H493 . 108.3 no C45 . C49 . H492 . 110.8 no H493 . C49 . H492 . 108.0 no C45 . C49 . H491 . 112.3 no H493 . C49 . H491 . 108.6 no H492 . C49 . H491 . 108.8 no _iucr_refine_instructions_details_constraints ; # # Punched on 31/07/13 at 11:30:36 # #LIST 12 BLOCK SCALE X'S, U'S RIDE B ( 1,X'S) H ( 11,X'S) RIDE N ( 30,X'S) H ( 301,X'S) H ( 302,X'S) RIDE C ( 42,X'S) H ( 421,X'S) H ( 422,X'S) RIDE C ( 43,X'S) H ( 431,X'S) H ( 432,X'S) RIDE C ( 44,X'S) H ( 441,X'S) H ( 442,X'S) RIDE C ( 46,X'S) H ( 463,X'S) H ( 462,X'S) H ( 461,X'S) RIDE C ( 47,X'S) H ( 471,X'S) H ( 472,X'S) H ( 473,X'S) RIDE C ( 48,X'S) H ( 483,X'S) H ( 482,X'S) H ( 481,X'S) RIDE C ( 49,X'S) H ( 493,X'S) H ( 492,X'S) H ( 491,X'S) END ; _iucr_refine_instructions_details_restraints ; # # Punched on 31/07/13 at 11:30:36 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 953644' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2-Neutron #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; . ; _chemical_name_common . _chemical_melting_point 'not measured' _chemical_formula_moiety 'C18 H B Cl5 F10, C9 H20 N' _chemical_formula_sum 'C27 H21 B Cl5 F10 N' _chemical_formula_weight 737.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0000 -0.2130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.011(3) _cell_length_b 17.343(4) _cell_length_c 13.332(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.030(15) _cell_angle_gamma 90.00 _cell_volume 2935.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1100 _cell_measurement_theta_min . _cell_measurement_theta_max . _exptl_crystal_description block _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_max 3.00 _exptl_crystal_size_mid 3.00 _exptl_crystal_size_min 2.00 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6579 _exptl_absorpt_correction_T_max 0.7504 _exptl_absorpt_process_details ; Calculated using custom ISIS software program SXD-2001. ; _exptl_special_details ; For peak integration a local UB matrix refined for each frame, using approximately 100 reflections per run from each of the 11 detectors. Hence _cell_measurement_reflns_used 1100 For final cell dimensions a weighted average of all local cells was calculated. Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.48-7.0 Angstroms, but the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. The data collection procedures on the SXD instrument used for the single crystal neutron data collection are most recently summarised in the Appendix to the following paper Wilson, C.C. (1997). J. Mol. Struct. 405, 207-217 ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength Laue _diffrn_radiation_type Neutron _diffrn_radiation_source 'ISIS spallation neutron source' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'SXD at ISIS neutron source' _diffrn_measurement_method 'time-of-flight Laue diffraction' _diffrn_detector_area_resol_mean . _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14355 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0770 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 7.69 _diffrn_reflns_theta_max 84.48 _reflns_number_total 14355 _reflns_number_gt 14355 _reflns_threshold_expression >2sigma(I) _computing_data_collection SXD2001 _computing_cell_refinement SXD2001 _computing_data_reduction SXD2001 _computing_structure_solution 'Refinement of known model' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics . _computing_publication_material . _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given. _refine_diff_density_max/min is given in Fermi per per angstrom cubed not electons per angstrom cubed. Another way to consider the _refine_diff_density_ is as a percentage of the diffracted intensity of a given atom: _refine_diff_density_max = 6.5% of Carbon _refine_diff_density_min = -6.2% of Carbon ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0941P)^2^+375.0044P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'From previously determined structure' _atom_sites_solution_secondary 'From previously determined structure' _atom_sites_solution_hydrogens 'From previously determined structure' _refine_ls_hydrogen_treatment anisotropic _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00099(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 14355 _refine_ls_number_parameters 596 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0928 _refine_ls_wR_factor_ref 0.2584 _refine_ls_wR_factor_gt 0.2584 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.7283(4) 0.4599(2) 0.3560(3) 0.0075(8) Uani 1 1 d . . . C1 C 0.7727(3) 0.4288(2) 0.2679(3) 0.0093(7) Uani 1 1 d . . . C2 C 0.7335(3) 0.3609(2) 0.2077(3) 0.0082(6) Uani 1 1 d . . . C3 C 0.7488(3) 0.3406(2) 0.1146(3) 0.0120(7) Uani 1 1 d . . . C4 C 0.8181(3) 0.3837(2) 0.0864(3) 0.0134(7) Uani 1 1 d . . . C5 C 0.8677(3) 0.4484(2) 0.1511(3) 0.0130(8) Uani 1 1 d . . . C6 C 0.8429(3) 0.4697(2) 0.2385(3) 0.0130(7) Uani 1 1 d . . . C7 C 0.7785(3) 0.4175(2) 0.4766(3) 0.0100(7) Uani 1 1 d . . . C8 C 0.8596(3) 0.3624(2) 0.5113(3) 0.0107(7) Uani 1 1 d . . . C9 C 0.9042(3) 0.3312(2) 0.6160(3) 0.0122(7) Uani 1 1 d . . . C10 C 0.8717(3) 0.3549(2) 0.6957(3) 0.0147(8) Uani 1 1 d . . . C11 C 0.7918(4) 0.4098(2) 0.6666(3) 0.0146(8) Uani 1 1 d . . . C12 C 0.7499(3) 0.4390(2) 0.5603(3) 0.0117(8) Uani 1 1 d . . . C13 C 0.5990(3) 0.4596(2) 0.2910(3) 0.0097(7) Uani 1 1 d . . . C14 C 0.5262(3) 0.4199(2) 0.3171(3) 0.0112(7) Uani 1 1 d . . . C15 C 0.4184(3) 0.4255(2) 0.2567(3) 0.0135(8) Uani 1 1 d . . . C16 C 0.3759(4) 0.4694(2) 0.1604(3) 0.0165(8) Uani 1 1 d . . . C17 C 0.4456(4) 0.5088(2) 0.1297(3) 0.0163(8) Uani 1 1 d . . . C18 C 0.5531(3) 0.5045(2) 0.1954(3) 0.0133(8) Uani 1 1 d . . . Cl1 Cl 0.9045(3) 0.5511(2) 0.3125(3) 0.0319(9) Uani 1 1 d . . . Cl2 Cl 0.9568(3) 0.4998(2) 0.1202(2) 0.0240(7) Uani 1 1 d . . . Cl3 Cl 0.8422(3) 0.35815(18) -0.0242(2) 0.0210(7) Uani 1 1 d . . . Cl4 Cl 0.6799(3) 0.26604(16) 0.0305(2) 0.0169(6) Uani 1 1 d . . . Cl5 Cl 0.6640(2) 0.29731(15) 0.2517(2) 0.0119(5) Uani 1 1 d . . . F1 F 0.8984(4) 0.3372(3) 0.4410(4) 0.0164(10) Uani 1 1 d . . . F2 F 0.9813(4) 0.2787(3) 0.6439(4) 0.0196(10) Uani 1 1 d . . . F3 F 0.9149(5) 0.3247(3) 0.7969(4) 0.0225(12) Uani 1 1 d . . . F4 F 0.7573(5) 0.4335(3) 0.7406(4) 0.0250(13) Uani 1 1 d . . . F5 F 0.6735(4) 0.4931(3) 0.5385(4) 0.0161(10) Uani 1 1 d . . . F6 F 0.5588(4) 0.3713(3) 0.4040(4) 0.0143(9) Uani 1 1 d . . . F7 F 0.3522(4) 0.3862(3) 0.2887(4) 0.0188(10) Uani 1 1 d . . . F8 F 0.2724(5) 0.4721(3) 0.0993(4) 0.0251(12) Uani 1 1 d . . . F9 F 0.4086(5) 0.5518(3) 0.0381(4) 0.0258(12) Uani 1 1 d . . . F10 F 0.6141(5) 0.5471(3) 0.1619(4) 0.0204(11) Uani 1 1 d . . . N30 N 0.7118(2) 0.64960(15) 0.4939(2) 0.0130(5) Uani 1 1 d . . . C41 C 0.8162(4) 0.6926(2) 0.5577(3) 0.0182(9) Uani 1 1 d . . . C42 C 0.7949(4) 0.7585(3) 0.6204(4) 0.0200(9) Uani 1 1 d . . . C43 C 0.7025(4) 0.8094(2) 0.5461(4) 0.0191(9) Uani 1 1 d . . . C44 C 0.6024(4) 0.7613(2) 0.4931(3) 0.0169(8) Uani 1 1 d . . . C45 C 0.6111(3) 0.6938(2) 0.4239(3) 0.0116(7) Uani 1 1 d . . . C46 C 0.8605(4) 0.7205(3) 0.4765(5) 0.0252(10) Uani 1 1 d . . . C47 C 0.8900(5) 0.6324(3) 0.6353(5) 0.0332(12) Uani 1 1 d . . . C48 C 0.5216(4) 0.6366(2) 0.3996(3) 0.0161(8) Uani 1 1 d . . . C49 C 0.6126(4) 0.7189(3) 0.3148(3) 0.0201(9) Uani 1 1 d . . . H11 H 0.7505(10) 0.5270(5) 0.3749(8) 0.035(2) Uani 1 1 d . . . H301 H 0.6962(8) 0.6200(5) 0.5523(7) 0.0280(19) Uani 1 1 d . . . H302 H 0.7241(8) 0.6069(5) 0.4460(8) 0.031(2) Uani 1 1 d . . . H421 H 0.7768(9) 0.7342(7) 0.6857(7) 0.039(2) Uani 1 1 d . . . H422 H 0.8671(10) 0.7930(7) 0.6603(9) 0.045(3) Uani 1 1 d . . . H431 H 0.6896(10) 0.8552(6) 0.5957(10) 0.043(3) Uani 1 1 d . . . H432 H 0.7213(9) 0.8388(6) 0.4843(8) 0.035(2) Uani 1 1 d . . . H441 H 0.5822(8) 0.7382(6) 0.5587(7) 0.031(2) Uani 1 1 d . . . H442 H 0.5353(9) 0.7965(6) 0.4386(9) 0.039(2) Uani 1 1 d . . . H463 H 0.9417(10) 0.7376(8) 0.5261(12) 0.054(3) Uani 1 1 d . . . H462 H 0.8590(11) 0.6755(7) 0.4205(11) 0.051(3) Uani 1 1 d . . . H461 H 0.8201(10) 0.7691(7) 0.4289(10) 0.046(3) Uani 1 1 d . . . H471 H 0.9650(11) 0.6596(9) 0.6867(11) 0.059(3) Uani 1 1 d . . . H472 H 0.8579(12) 0.6086(8) 0.6905(11) 0.061(4) Uani 1 1 d . . . H473 H 0.9062(12) 0.5856(7) 0.5903(11) 0.058(3) Uani 1 1 d . . . H481 H 0.4466(9) 0.6656(7) 0.3554(10) 0.042(2) Uani 1 1 d . . . H482 H 0.5264(9) 0.5901(6) 0.3486(8) 0.038(2) Uani 1 1 d . . . H483 H 0.5208(9) 0.6127(6) 0.4741(8) 0.037(2) Uani 1 1 d . . . H491 H 0.6648(10) 0.7664(7) 0.3244(9) 0.045(3) Uani 1 1 d . . . H492 H 0.6363(10) 0.6718(6) 0.2755(8) 0.042(3) Uani 1 1 d . . . H493 H 0.5332(10) 0.7375(7) 0.2572(8) 0.046(3) Uani 1 1 d . . . 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 0.009(2) 0.0072(17) 0.0073(16) -0.0009(13) 0.0046(18) -0.0027(16) C1 0.012(2) 0.0102(15) 0.0072(14) -0.0028(11) 0.0054(15) -0.0042(14) C2 0.0066(18) 0.0091(14) 0.0076(13) -0.0002(11) 0.0018(14) 0.0005(14) C3 0.015(2) 0.0126(16) 0.0072(14) -0.0004(12) 0.0038(15) 0.0029(15) C4 0.013(2) 0.0194(17) 0.0079(14) 0.0015(12) 0.0043(16) 0.0024(15) C5 0.014(2) 0.0192(18) 0.0072(14) 0.0027(12) 0.0058(16) -0.0015(16) C6 0.015(2) 0.0144(17) 0.0113(15) -0.0024(13) 0.0070(16) -0.0066(15) C7 0.010(2) 0.0132(16) 0.0061(14) 0.0009(11) 0.0031(15) -0.0001(14) C8 0.0054(19) 0.0186(17) 0.0048(13) 0.0000(12) -0.0009(14) 0.0007(15) C9 0.010(2) 0.0165(17) 0.0072(14) -0.0001(12) 0.0014(15) -0.0010(15) C10 0.016(2) 0.0192(19) 0.0075(14) 0.0026(13) 0.0038(16) 0.0027(16) C11 0.020(2) 0.0192(18) 0.0055(14) 0.0015(12) 0.0065(17) 0.0039(16) C12 0.016(2) 0.0110(16) 0.0105(15) -0.0010(11) 0.0080(17) 0.0005(14) C13 0.010(2) 0.0106(15) 0.0061(13) -0.0003(11) 0.0013(15) -0.0002(14) C14 0.012(2) 0.0096(16) 0.0137(15) 0.0018(12) 0.0074(16) 0.0020(14) C15 0.012(2) 0.0112(16) 0.0156(17) -0.0037(13) 0.0043(17) 0.0001(15) C16 0.014(2) 0.0163(19) 0.0155(17) -0.0018(13) 0.0030(18) 0.0050(16) C17 0.018(2) 0.0167(18) 0.0092(15) 0.0003(13) 0.0007(17) 0.0044(16) C18 0.019(2) 0.0113(16) 0.0096(14) 0.0044(12) 0.0067(17) 0.0030(15) Cl1 0.044(2) 0.0317(18) 0.0312(16) -0.0194(13) 0.0265(18) -0.0279(17) Cl2 0.0232(18) 0.0349(17) 0.0195(13) 0.0011(12) 0.0146(14) -0.0090(15) Cl3 0.0294(19) 0.0264(15) 0.0126(11) 0.0018(10) 0.0139(13) 0.0072(14) Cl4 0.0187(17) 0.0145(12) 0.0150(12) -0.0076(9) 0.0047(13) 0.0013(11) Cl5 0.0099(14) 0.0104(11) 0.0151(11) -0.0013(9) 0.0050(11) -0.0027(10) F1 0.015(3) 0.025(2) 0.0108(18) 0.0033(16) 0.007(2) 0.007(2) F2 0.015(3) 0.028(3) 0.014(2) 0.0041(17) 0.003(2) 0.005(2) F3 0.032(3) 0.025(3) 0.0091(19) 0.0042(16) 0.007(2) 0.006(2) F4 0.040(4) 0.026(3) 0.014(2) 0.0012(18) 0.016(2) 0.011(2) F5 0.021(3) 0.016(2) 0.0122(19) 0.0037(15) 0.009(2) 0.008(2) F6 0.015(3) 0.013(2) 0.0170(19) 0.0044(15) 0.009(2) 0.0009(18) F7 0.006(3) 0.021(2) 0.028(2) -0.0007(19) 0.007(2) 0.003(2) F8 0.013(3) 0.031(3) 0.024(3) -0.003(2) 0.001(2) 0.011(2) F9 0.033(4) 0.026(3) 0.013(2) 0.0068(18) 0.003(2) 0.012(2) F10 0.031(3) 0.016(2) 0.016(2) 0.0051(16) 0.013(2) -0.002(2) N30 0.0110(15) 0.0127(12) 0.0132(11) 0.0012(9) 0.0030(11) 0.0032(11) C41 0.015(2) 0.0148(18) 0.024(2) -0.0007(15) 0.007(2) 0.0051(17) C42 0.016(3) 0.018(2) 0.022(2) -0.0065(15) 0.003(2) -0.0011(18) C43 0.016(2) 0.0147(18) 0.025(2) -0.0049(16) 0.0072(19) 0.0023(17) C44 0.016(2) 0.0124(17) 0.025(2) -0.0023(15) 0.011(2) 0.0051(17) C45 0.011(2) 0.0096(15) 0.0138(16) 0.0018(12) 0.0050(16) 0.0027(14) C46 0.016(3) 0.025(2) 0.039(3) -0.003(2) 0.016(2) 0.000(2) C47 0.025(3) 0.025(3) 0.034(3) 0.005(2) -0.002(3) 0.010(2) C48 0.016(2) 0.0151(17) 0.0176(17) 0.0005(14) 0.0075(18) 0.0039(17) C49 0.023(3) 0.022(2) 0.0145(18) 0.0048(14) 0.007(2) 0.0055(19) H11 0.056(7) 0.018(4) 0.034(4) -0.013(3) 0.021(5) -0.012(4) H301 0.032(6) 0.024(4) 0.027(4) 0.007(3) 0.012(4) -0.002(4) H302 0.030(6) 0.024(4) 0.035(5) -0.005(3) 0.011(4) 0.008(4) H421 0.039(7) 0.049(6) 0.020(4) -0.002(4) 0.004(4) 0.003(5) H422 0.034(7) 0.040(6) 0.045(6) -0.018(5) 0.001(5) -0.010(5) H431 0.044(7) 0.025(5) 0.065(7) -0.022(5) 0.027(6) -0.003(5) H432 0.035(6) 0.028(5) 0.039(5) 0.005(4) 0.011(5) -0.004(4) H441 0.026(5) 0.038(5) 0.032(4) -0.008(4) 0.016(4) -0.009(4) H442 0.028(6) 0.035(5) 0.047(6) -0.006(4) 0.008(5) 0.012(5) H463 0.032(8) 0.061(8) 0.076(9) -0.011(7) 0.028(7) -0.011(6) H462 0.060(9) 0.049(7) 0.064(7) -0.016(6) 0.044(7) -0.008(6) H461 0.042(7) 0.048(7) 0.060(7) 0.020(6) 0.032(6) 0.011(6) H471 0.031(8) 0.064(9) 0.052(7) -0.008(6) -0.013(6) 0.001(7) H472 0.064(10) 0.053(7) 0.060(7) 0.031(6) 0.021(7) 0.022(7) H473 0.061(10) 0.040(7) 0.058(7) 0.000(5) 0.011(7) 0.025(6) H481 0.024(6) 0.043(6) 0.053(6) 0.006(5) 0.011(5) 0.004(5) H482 0.044(7) 0.030(5) 0.040(5) -0.014(4) 0.019(5) -0.004(5) H483 0.035(6) 0.050(6) 0.034(5) 0.000(4) 0.020(5) -0.010(5) H491 0.045(8) 0.042(6) 0.049(6) 0.017(5) 0.021(6) -0.007(6) H492 0.066(8) 0.041(6) 0.031(5) 0.002(4) 0.032(6) 0.014(5) H493 0.038(7) 0.063(7) 0.024(4) 0.016(5) 0.000(5) 0.014(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C7 1.632(5) . ? B1 C1 1.636(5) . ? B1 C13 1.644(6) . ? B1 H11 1.203(9) . ? C1 C6 1.397(5) . ? C1 C2 1.400(5) . ? C2 C3 1.392(4) . ? C2 Cl5 1.729(4) . ? C3 C4 1.396(6) . ? C3 Cl4 1.717(5) . ? C4 C5 1.406(6) . ? C4 Cl3 1.705(4) . ? C5 C6 1.400(4) . ? C5 Cl2 1.720(5) . ? C6 Cl1 1.728(5) . ? C7 C12 1.388(4) . ? C7 C8 1.404(5) . ? C8 F1 1.341(5) . ? C8 C9 1.376(5) . ? C9 F2 1.341(7) . ? C9 C10 1.385(5) . ? C10 F3 1.331(6) . ? C10 C11 1.393(6) . ? C11 F4 1.335(5) . ? C11 C12 1.380(5) . ? C12 F5 1.359(6) . ? C13 C14 1.392(5) . ? C13 C18 1.397(5) . ? C14 F6 1.346(6) . ? C14 C15 1.382(6) . ? C15 F7 1.357(6) . ? C15 C16 1.391(6) . ? C16 F8 1.329(7) . ? C16 C17 1.389(6) . ? C17 F9 1.334(6) . ? C17 C18 1.387(6) . ? C18 F10 1.341(6) . ? N30 C45 1.529(5) . ? N30 C41 1.539(6) . ? N30 H301 1.030(8) . ? N30 H302 1.038(9) . ? C41 C42 1.519(6) . ? C41 C47 1.524(7) . ? C41 C46 1.536(6) . ? C42 C43 1.533(7) . ? C42 H421 1.089(11) . ? C42 H422 1.100(13) . ? C43 C44 1.523(7) . ? C43 H431 1.097(10) . ? C43 H432 1.091(10) . ? C44 C45 1.527(5) . ? C44 H441 1.102(9) . ? C44 H442 1.099(13) . ? C45 C48 1.523(6) . ? C45 C49 1.526(5) . ? C46 H463 1.088(16) . ? C46 H462 1.074(12) . ? C46 H461 1.063(14) . ? C47 H471 1.089(16) . ? C47 H472 1.093(16) . ? C47 H473 1.090(14) . ? C48 H483 1.080(9) . ? C48 H482 1.075(10) . ? C48 H481 1.086(13) . ? C49 H493 1.100(13) . ? C49 H492 1.094(10) . ? C49 H491 1.073(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 B1 C1 115.0(3) . . ? C7 B1 C13 116.0(3) . . ? C1 B1 C13 106.8(3) . . ? C7 B1 H11 105.4(6) . . ? C1 B1 H11 108.9(5) . . ? C13 B1 H11 104.1(7) . . ? C6 C1 C2 114.7(3) . . ? C6 C1 B1 124.2(3) . . ? C2 C1 B1 120.8(3) . . ? C3 C2 C1 123.6(3) . . ? C3 C2 Cl5 117.6(3) . . ? C1 C2 Cl5 118.9(2) . . ? C2 C3 C4 119.5(4) . . ? C2 C3 Cl4 121.1(3) . . ? C4 C3 Cl4 119.4(3) . . ? C3 C4 C5 118.8(3) . . ? C3 C4 Cl3 120.5(3) . . ? C5 C4 Cl3 120.7(3) . . ? C6 C5 C4 119.2(3) . . ? C6 C5 Cl2 121.6(3) . . ? C4 C5 Cl2 119.2(3) . . ? C1 C6 C5 123.5(4) . . ? C1 C6 Cl1 119.7(3) . . ? C5 C6 Cl1 116.8(3) . . ? C12 C7 C8 112.8(3) . . ? C12 C7 B1 121.3(3) . . ? C8 C7 B1 125.6(3) . . ? F1 C8 C9 115.8(4) . . ? F1 C8 C7 120.2(3) . . ? C9 C8 C7 123.9(3) . . ? F2 C9 C8 121.1(3) . . ? F2 C9 C10 118.5(4) . . ? C8 C9 C10 120.5(4) . . ? F3 C10 C9 120.3(4) . . ? F3 C10 C11 121.3(4) . . ? C9 C10 C11 118.4(3) . . ? F4 C11 C12 121.1(4) . . ? F4 C11 C10 120.3(4) . . ? C12 C11 C10 118.7(3) . . ? F5 C12 C11 115.3(3) . . ? F5 C12 C7 118.9(3) . . ? C11 C12 C7 125.8(4) . . ? C14 C13 C18 113.6(4) . . ? C14 C13 B1 129.1(3) . . ? C18 C13 B1 117.3(3) . . ? F6 C14 C15 115.8(4) . . ? F6 C14 C13 120.5(4) . . ? C15 C14 C13 123.8(3) . . ? F7 C15 C14 120.4(4) . . ? F7 C15 C16 118.8(4) . . ? C14 C15 C16 120.8(4) . . ? F8 C16 C17 121.5(4) . . ? F8 C16 C15 121.0(4) . . ? C17 C16 C15 117.5(4) . . ? F9 C17 C18 120.4(4) . . ? F9 C17 C16 119.7(5) . . ? C18 C17 C16 119.9(4) . . ? F10 C18 C17 115.8(4) . . ? F10 C18 C13 119.9(4) . . ? C17 C18 C13 124.3(4) . . ? C45 N30 C41 120.7(3) . . ? C45 N30 H301 106.0(6) . . ? C41 N30 H301 106.2(6) . . ? C45 N30 H302 109.5(6) . . ? C41 N30 H302 108.6(7) . . ? H301 N30 H302 104.6(8) . . ? C42 C41 C47 112.1(4) . . ? C42 C41 C46 112.6(4) . . ? C47 C41 C46 109.5(4) . . ? C42 C41 N30 107.9(3) . . ? C47 C41 N30 104.8(4) . . ? C46 C41 N30 109.6(4) . . ? C41 C42 C43 112.7(4) . . ? C41 C42 H421 108.4(7) . . ? C43 C42 H421 108.8(7) . . ? C41 C42 H422 108.6(7) . . ? C43 C42 H422 110.7(8) . . ? H421 C42 H422 107.5(9) . . ? C44 C43 C42 110.2(4) . . ? C44 C43 H431 108.8(7) . . ? C42 C43 H431 109.7(8) . . ? C44 C43 H432 112.0(7) . . ? C42 C43 H432 110.5(7) . . ? H431 C43 H432 105.6(9) . . ? C43 C44 C45 114.0(3) . . ? C43 C44 H441 109.1(6) . . ? C45 C44 H441 108.3(6) . . ? C43 C44 H442 111.4(7) . . ? C45 C44 H442 106.9(6) . . ? H441 C44 H442 106.9(9) . . ? C48 C45 C49 109.0(3) . . ? C48 C45 C44 111.1(3) . . ? C49 C45 C44 113.2(3) . . ? C48 C45 N30 105.5(3) . . ? C49 C45 N30 110.1(3) . . ? C44 C45 N30 107.7(3) . . ? C41 C46 H463 106.7(8) . . ? C41 C46 H462 111.5(7) . . ? H463 C46 H462 109.2(11) . . ? C41 C46 H461 113.5(7) . . ? H463 C46 H461 107.6(11) . . ? H462 C46 H461 108.3(11) . . ? C41 C47 H471 109.1(9) . . ? C41 C47 H472 111.3(8) . . ? H471 C47 H472 107.6(12) . . ? C41 C47 H473 112.1(8) . . ? H471 C47 H473 107.4(12) . . ? H472 C47 H473 109.3(12) . . ? C45 C48 H483 112.5(7) . . ? C45 C48 H482 110.9(7) . . ? H483 C48 H482 108.7(9) . . ? C45 C48 H481 109.5(7) . . ? H483 C48 H481 107.1(9) . . ? H482 C48 H481 108.0(10) . . ? C45 C49 H493 109.4(7) . . ? C45 C49 H492 111.9(6) . . ? H493 C49 H492 107.8(10) . . ? C45 C49 H491 112.9(7) . . ? H493 C49 H491 107.1(10) . . ? H492 C49 H491 107.5(10) . . ? _diffrn_measured_fraction_theta_max 0.069 _diffrn_reflns_theta_full 84.48 _diffrn_measured_fraction_theta_full 0.069 _refine_diff_density_max 1.780 _refine_diff_density_min -1.701 _refine_diff_density_rms 0.365 #============================================================================== # start Validation Reply Form #============================================================================== _vrf_PLAT415_2-X-ray ; PROBLEM: Short Inter D-H..H-X H11 .. H302 .. 1.84 Ang. RESPONSE: The study investigates trapping and splitting of hydrogen; the short contact is due to sample preparation methods. ; _vrf_TYPE031_2-Neutron ; PROBLEM: _diffrn_radiation_wavelength is not of type numb. RESPONSE: Data collected with Time of Flight Neutron Diffraction Data; see _exptl_special_details and _refine_special_details for information. ; _vrf_CELL004_2-Neutron ; PROBLEM: _cell_measurement_theta_min is missing RESPONSE: Data collected with Time of Flight Neutron Diffraction Data; see _exptl_special_details and _refine_special_details for information. ; _vrf_CELL005_2-Neutron ; PROBLEM: _cell_measurement_theta_max is missing RESPONSE: Data collected with Time of Flight Neutron Diffraction Data; see _exptl_special_details and _refine_special_details for information. ; _vrf_PLAT022_2-Neutron ; PROBLEM: Ratio Unique / Expected Reflections (too) Low .. 0.069 RESPONSE: Data collected with Time of Flight Neutron Diffraction Data; see _exptl_special_details and _refine_special_details for information. ; _vrf_PLAT029_2-Neutron ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.069 RESPONSE: Data collected with Time of Flight Neutron Diffraction Data; see _exptl_special_details and _refine_special_details for information. ; _vrf_PLAT051_2-Neutron ; PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 281.46 Perc. RESPONSE: Data collected with Time of Flight Neutron Diffraction Data; see _exptl_special_details and _refine_special_details for information. ; _vrf_PLAT091_2-Neutron ; PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed ? RESPONSE: Data collected with Time of Flight Neutron Diffraction Data; see _exptl_special_details and _refine_special_details for information. ; _vrf_PLAT415_2-Neutron ; PROBLEM: Short Inter D-H..H-X H11 .. H302 .. 1.80 Ang. RESPONSE: The study investigates trapping and splitting of hydrogen; the short contact is due to sample preparation methods. ; #============================================================================== # End Validation Reply Form #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 953645'