# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email Philip.Bailey@ed.ac.uk _publ_contact_author_name P.Bailey _publ_contact_author_address ; Department of Chemistry, Joseph Black Building, West Mains Road, Edinburgh, EH9 3JJ ; _publ_contact_author_phone '+44 (0)131 6504804' loop_ _publ_author_name P.J.Bailey N.L.Bell 'Lim Li Gim' 'Tai Yucheng' N.Funnell F.White S.Parsons data_pb9009 #(Compound 2 in the manuscript) _database_code_depnum_ccdc_archive 'CCDC 829912' #TrackingRef '- Compound 2 & 3 CIF files.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_compound_source 'Lim Li Gim' _exptl_crystal_recrystallization_method 'slow diffusion of diethyl ether into dichloromethane solution' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 B N5 O3' _chemical_formula_sum 'C22 H22 B N5 O3' _chemical_formula_weight 415.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.5746(2) _cell_length_b 10.6207(2) _cell_length_c 16.5475(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.5990(10) _cell_angle_gamma 90.00 _cell_volume 2030.18(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16956 _cell_measurement_theta_min 2.214 _cell_measurement_theta_max 30.46 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8857 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD' _diffrn_measurement_method 'Phi and Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 38547 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 30.50 _reflns_number_total 5167 _reflns_number_gt 4101 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'Shelxs Sheldrick' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics Shelxp _computing_publication_material 'Platon, encifer' _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 Following Improvement and Query ALERTS were generated - (Acta-Mode) <<< #============================================================================== 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 989 Completeness is better than 99% to 55 deg in 2 theta. 128_ALERT_4_G Non-standard setting of Space-group P21/c .... P21/n Use of P21/n minimises the beta angle 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? No action taken ; _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^)+(0.0429P)^2^+0.6633P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5167 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1004 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.002 _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 C1 C 0.09618(12) 0.29658(12) 0.08527(8) 0.0298(3) Uani 1 1 d . . . H1A H 0.0677 0.2231 0.0542 0.045 Uiso 1 1 calc R . . H1B H 0.1184 0.2711 0.1410 0.045 Uiso 1 1 calc R . . H1C H 0.1637 0.3317 0.0603 0.045 Uiso 1 1 calc R . . C2 C -0.11065(12) 0.35610(13) 0.05357(8) 0.0294(3) Uani 1 1 d . . . H2A H -0.1073 0.2736 0.0273 0.044 Uiso 1 1 calc R . . H2B H -0.1396 0.4190 0.0140 0.044 Uiso 1 1 calc R . . H2C H -0.1627 0.3516 0.0979 0.044 Uiso 1 1 calc R . . N3 N 0.00491(9) 0.39185(10) 0.08564(6) 0.0240(2) Uani 1 1 d . . . C4 C 0.02326(10) 0.50518(11) 0.12061(7) 0.0199(2) Uani 1 1 d . . . C5 C 0.13194(10) 0.54018(11) 0.15813(7) 0.0217(2) Uani 1 1 d . . . H5 H 0.1942 0.4818 0.1607 0.026 Uiso 1 1 calc R . . C6 C 0.14727(10) 0.65756(11) 0.19054(7) 0.0206(2) Uani 1 1 d . . . H6 H 0.2207 0.6780 0.2161 0.025 Uiso 1 1 calc R . . N7 N 0.06303(8) 0.74648(9) 0.18811(6) 0.0183(2) Uani 1 1 d . . . C8 C -0.04108(10) 0.71427(12) 0.15339(7) 0.0213(2) Uani 1 1 d . . . H8 H -0.1011 0.7754 0.1512 0.026 Uiso 1 1 calc R . . C9 C -0.06456(10) 0.59790(12) 0.12105(7) 0.0218(2) Uani 1 1 d . . . H9 H -0.1402 0.5792 0.0987 0.026 Uiso 1 1 calc R . . B10 B 0.09039(11) 0.88009(13) 0.22865(8) 0.0192(3) Uani 1 1 d . . . O11 O 0.19613(7) 0.93006(8) 0.19745(5) 0.02004(18) Uani 1 1 d . . . C12 C 0.21032(10) 0.96751(10) 0.12128(7) 0.0180(2) Uani 1 1 d . . . N13 N 0.12715(8) 0.94835(10) 0.06341(6) 0.0213(2) Uani 1 1 d . . . C14 C 0.14775(11) 0.98895(12) -0.01179(7) 0.0233(3) Uani 1 1 d . . . H14 H 0.0885 0.9779 -0.0536 0.028 Uiso 1 1 calc R . . C15 C 0.24936(11) 1.04533(11) -0.03138(7) 0.0231(3) Uani 1 1 d . . . H15 H 0.2600 1.0719 -0.0852 0.028 Uiso 1 1 calc R . . C16 C 0.33619(11) 1.06251(11) 0.02975(8) 0.0231(3) Uani 1 1 d . . . H16 H 0.4079 1.0997 0.0181 0.028 Uiso 1 1 calc R . . C17 C 0.31663(10) 1.02481(11) 0.10726(7) 0.0210(2) Uani 1 1 d . . . H17 H 0.3737 1.0372 0.1503 0.025 Uiso 1 1 calc R . . O18 O -0.01568(7) 0.95167(8) 0.21386(5) 0.02042(18) Uani 1 1 d . . . C19 C -0.03328(10) 1.06912(11) 0.24043(7) 0.0199(2) Uani 1 1 d . . . N20 N 0.05650(9) 1.14043(10) 0.26728(7) 0.0255(2) Uani 1 1 d . . . C21 C 0.03305(11) 1.26018(12) 0.28846(8) 0.0271(3) Uani 1 1 d . . . H21 H 0.0959 1.3119 0.3076 0.033 Uiso 1 1 calc R . . C22 C -0.07618(12) 1.31187(13) 0.28401(8) 0.0282(3) Uani 1 1 d . . . H22 H -0.0883 1.3972 0.2985 0.034 Uiso 1 1 calc R . . C23 C -0.16791(11) 1.23517(13) 0.25770(8) 0.0297(3) Uani 1 1 d . . . H23 H -0.2447 1.2672 0.2547 0.036 Uiso 1 1 calc R . . C24 C -0.14720(10) 1.11234(13) 0.23597(8) 0.0254(3) Uani 1 1 d . . . H24 H -0.2092 1.0583 0.2183 0.031 Uiso 1 1 calc R . . O25 O 0.12606(7) 0.86480(8) 0.31455(5) 0.02017(18) Uani 1 1 d . . . C26 C 0.05361(10) 0.83416(11) 0.37186(7) 0.0196(2) Uani 1 1 d . . . N27 N -0.04084(9) 0.76620(10) 0.35202(6) 0.0244(2) Uani 1 1 d . . . C28 C -0.10822(11) 0.73645(13) 0.41278(8) 0.0283(3) Uani 1 1 d . . . H28 H -0.1757 0.6878 0.3998 0.034 Uiso 1 1 calc R . . C29 C -0.08608(12) 0.77167(13) 0.49218(8) 0.0304(3) Uani 1 1 d . . . H29 H -0.1366 0.7482 0.5327 0.036 Uiso 1 1 calc R . . C30 C 0.01254(13) 0.84267(12) 0.51126(8) 0.0301(3) Uani 1 1 d . . . H30 H 0.0309 0.8690 0.5654 0.036 Uiso 1 1 calc R . . C31 C 0.08350(11) 0.87443(12) 0.45066(7) 0.0251(3) Uani 1 1 d . . . H31 H 0.1515 0.9229 0.4623 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0388(7) 0.0207(6) 0.0301(7) -0.0017(5) 0.0027(5) 0.0040(5) C2 0.0322(7) 0.0272(7) 0.0287(7) -0.0038(5) -0.0001(5) -0.0101(5) N3 0.0261(5) 0.0201(5) 0.0257(5) -0.0018(4) 0.0016(4) -0.0022(4) C4 0.0236(6) 0.0200(6) 0.0164(5) 0.0024(4) 0.0029(4) -0.0020(4) C5 0.0218(6) 0.0222(6) 0.0209(6) 0.0022(5) -0.0010(4) 0.0032(5) C6 0.0178(5) 0.0242(6) 0.0195(6) 0.0024(5) -0.0015(4) 0.0008(4) N7 0.0164(5) 0.0202(5) 0.0181(5) 0.0015(4) 0.0003(4) -0.0009(4) C8 0.0164(5) 0.0237(6) 0.0237(6) -0.0002(5) 0.0008(4) -0.0001(4) C9 0.0163(5) 0.0248(6) 0.0242(6) -0.0013(5) 0.0009(4) -0.0032(4) B10 0.0180(6) 0.0198(6) 0.0197(6) 0.0005(5) 0.0012(5) -0.0018(5) O11 0.0182(4) 0.0227(4) 0.0191(4) 0.0017(3) 0.0007(3) -0.0035(3) C12 0.0196(5) 0.0147(5) 0.0199(5) 0.0003(4) 0.0024(4) 0.0012(4) N13 0.0194(5) 0.0224(5) 0.0220(5) 0.0006(4) 0.0007(4) -0.0007(4) C14 0.0228(6) 0.0264(6) 0.0204(6) -0.0001(5) 0.0001(4) 0.0026(5) C15 0.0275(6) 0.0211(6) 0.0212(6) 0.0020(5) 0.0063(5) 0.0022(5) C16 0.0233(6) 0.0183(6) 0.0284(6) 0.0006(5) 0.0070(5) -0.0024(5) C17 0.0191(6) 0.0191(6) 0.0248(6) -0.0014(5) 0.0009(4) -0.0022(4) O18 0.0188(4) 0.0196(4) 0.0227(4) -0.0009(3) -0.0003(3) 0.0005(3) C19 0.0223(6) 0.0216(6) 0.0159(5) 0.0023(4) 0.0024(4) 0.0006(4) N20 0.0246(5) 0.0233(5) 0.0285(6) -0.0027(4) 0.0004(4) -0.0017(4) C21 0.0304(7) 0.0242(6) 0.0267(6) -0.0031(5) 0.0011(5) -0.0039(5) C22 0.0363(7) 0.0241(7) 0.0249(6) -0.0013(5) 0.0080(5) 0.0049(5) C23 0.0242(6) 0.0359(8) 0.0297(7) 0.0021(6) 0.0056(5) 0.0080(5) C24 0.0190(6) 0.0302(7) 0.0272(6) 0.0021(5) 0.0021(5) -0.0008(5) O25 0.0184(4) 0.0236(4) 0.0185(4) 0.0013(3) 0.0013(3) -0.0027(3) C26 0.0202(5) 0.0166(6) 0.0224(6) 0.0028(4) 0.0036(4) 0.0031(4) N27 0.0197(5) 0.0270(6) 0.0265(5) 0.0043(4) 0.0018(4) -0.0007(4) C28 0.0192(6) 0.0299(7) 0.0362(7) 0.0093(6) 0.0053(5) 0.0016(5) C29 0.0306(7) 0.0296(7) 0.0324(7) 0.0086(6) 0.0144(5) 0.0093(5) C30 0.0447(8) 0.0243(7) 0.0219(6) -0.0007(5) 0.0077(5) 0.0081(6) C31 0.0327(7) 0.0197(6) 0.0230(6) -0.0015(5) 0.0024(5) -0.0005(5) _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 C1 N3 1.4631(16) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N3 1.4580(16) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? N3 C4 1.3466(16) . ? C4 C9 1.4156(17) . ? C4 C5 1.4171(16) . ? C5 C6 1.3643(17) . ? C5 H5 0.9500 . ? C6 N7 1.3563(15) . ? C6 H6 0.9500 . ? N7 C8 1.3462(15) . ? N7 B10 1.5928(16) . ? C8 C9 1.3672(17) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? B10 O18 1.4518(15) . ? B10 O11 1.4578(15) . ? B10 O25 1.4641(15) . ? O11 C12 1.3416(14) . ? C12 N13 1.3302(15) . ? C12 C17 1.4050(16) . ? N13 C14 1.3522(16) . ? C14 C15 1.3766(17) . ? C14 H14 0.9500 . ? C15 C16 1.3925(18) . ? C15 H15 0.9500 . ? C16 C17 1.3758(17) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? O18 C19 1.3425(14) . ? C19 N20 1.3390(16) . ? C19 C24 1.3937(16) . ? N20 C21 1.3513(17) . ? C21 C22 1.3761(19) . ? C21 H21 0.9500 . ? C22 C23 1.3865(19) . ? C22 H22 0.9500 . ? C23 C24 1.3782(19) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? O25 C26 1.3447(14) . ? C26 N27 1.3338(15) . ? C26 C31 1.3950(17) . ? N27 C28 1.3481(16) . ? C28 C29 1.375(2) . ? C28 H28 0.9500 . ? C29 C30 1.388(2) . ? C29 H29 0.9500 . ? C30 C31 1.3775(18) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? 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 N3 C1 H1A 109.5 . . ? N3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N3 C2 H2A 109.5 . . ? N3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 N3 C2 120.37(11) . . ? C4 N3 C1 121.70(10) . . ? C2 N3 C1 117.68(10) . . ? N3 C4 C9 122.01(11) . . ? N3 C4 C5 122.31(11) . . ? C9 C4 C5 115.67(11) . . ? C6 C5 C4 120.13(11) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? N7 C6 C5 123.31(11) . . ? N7 C6 H6 118.3 . . ? C5 C6 H6 118.3 . . ? C8 N7 C6 117.28(10) . . ? C8 N7 B10 123.72(10) . . ? C6 N7 B10 118.96(9) . . ? N7 C8 C9 123.19(11) . . ? N7 C8 H8 118.4 . . ? C9 C8 H8 118.4 . . ? C8 C9 C4 120.37(11) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? O18 B10 O11 118.00(10) . . ? O18 B10 O25 113.93(10) . . ? O11 B10 O25 101.09(9) . . ? O18 B10 N7 104.58(9) . . ? O11 B10 N7 108.93(9) . . ? O25 B10 N7 110.27(9) . . ? C12 O11 B10 126.56(9) . . ? N13 C12 O11 120.35(10) . . ? N13 C12 C17 123.30(11) . . ? O11 C12 C17 116.35(10) . . ? C12 N13 C14 116.90(10) . . ? N13 C14 C15 123.92(11) . . ? N13 C14 H14 118.0 . . ? C15 C14 H14 118.0 . . ? C14 C15 C16 118.32(11) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? C17 C16 C15 119.05(11) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? C16 C17 C12 118.50(11) . . ? C16 C17 H17 120.7 . . ? C12 C17 H17 120.7 . . ? C19 O18 B10 125.13(9) . . ? N20 C19 O18 120.24(10) . . ? N20 C19 C24 122.91(11) . . ? O18 C19 C24 116.82(11) . . ? C19 N20 C21 117.00(11) . . ? N20 C21 C22 124.09(12) . . ? N20 C21 H21 118.0 . . ? C22 C21 H21 118.0 . . ? C21 C22 C23 117.73(12) . . ? C21 C22 H22 121.1 . . ? C23 C22 H22 121.1 . . ? C24 C23 C22 119.72(12) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C19 118.52(12) . . ? C23 C24 H24 120.7 . . ? C19 C24 H24 120.7 . . ? C26 O25 B10 124.14(9) . . ? N27 C26 O25 119.68(11) . . ? N27 C26 C31 123.19(11) . . ? O25 C26 C31 117.12(11) . . ? C26 N27 C28 116.54(11) . . ? N27 C28 C29 124.55(12) . . ? N27 C28 H28 117.7 . . ? C29 C28 H28 117.7 . . ? C28 C29 C30 117.82(12) . . ? C28 C29 H29 121.1 . . ? C30 C29 H29 121.1 . . ? C31 C30 C29 119.14(12) . . ? C31 C30 H30 120.4 . . ? C29 C30 H30 120.4 . . ? C30 C31 C26 118.76(12) . . ? C30 C31 H31 120.6 . . ? C26 C31 H31 120.6 . . ? _diffrn_measured_fraction_theta_max 0.833 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.288 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.043 #------------------------------------------------------------------- data_pb1003 #(Compound 3 in the manuscript) _database_code_depnum_ccdc_archive 'CCDC 829913' #TrackingRef '- Compound 2 & 3 CIF files.cif' _audit_creation_date 11-03-28 _audit_creation_method CRYSTALS_ver_14.06 _oxford_structure_analysis_title 'pb1003 in P2(1)/c' _publ_section_exptl_refinement ; In the absence of anomalous scattering, Friedel pairs were merged Hydrogen atoms were placed geometrically and constrained to ride on their host atoms. Check-cif alerts 220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.35 Ratio This is a limitation in Crystals. Ideally the atom should be split over two sites but it is already part of a disordered group. It requires a 'group within a group'. 042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? They total number of atoms in each is the same. The formula given is intended to be more chemically meaningful 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 58 The data collection strategy used expected higher angle data that were not collected, which have been included in the refinement. Resolution and completeness statistics are given below #============================================================================== Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 50.44 0.500 1.000 3278 3278 0 58.00 0.550 1.000 4377 4376 1 67.68 0.600 1.000 5674 5674 0 #----------------------------------------------------------- #ACTA Min. Res. --- 72.85 0.620 0.991 6255 6197 58 Note: The Reported Completeness refers to the Actual H,K,L Index Range 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of Cl201 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of Cl202 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C200 244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors of C204 302_ALERT_4_G Note: Anion/Solvent Disorder ................... 47.00 Perc. 301_ALERT_3_G Note: Main Residue Disorder ................... 8.00 Perc. 432_ALERT_2_G Short Inter X...Y Contact Cl203 .. C29 .. 3.21 Ang. 860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 15 There are two disordered chloroform molecules in the structure both of which are modelled over two sites each, to varying extents. Restraints were used to maintain sensible anisotropic displacement parameters (given below). Additionally, the dimethylamino group was disordered over 2 sites. U(IJ)'S 0.0, 0.010000 = C(204) TO CL(205) VIBRATION 0.0, 0.010000 = CL(205) TO C(204) U(IJ)'S 0.0, 0.010000 = CL(206) TO C(204) VIBRATION 0.0, 0.020000 = CL(206) TO C(204) U(IJ)'S 0.0, 0.010000 = CL(207) TO C(204) VIBRATION 0.0, 0.020000 = CL(207) TO C(204) 720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 27 The labels given are intended to be chemically meaningful 811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! The ADDSYM test for missed symmetry is not executed for structures with too many disordered atoms. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! This is a bug in checkcif; these items are available below. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? Noted, no action ; _publ_section_exptl_prep ; Reaction of (DMAP)B(2-hydroxypyridine)3 with copper(triphenylphospine) chloride in dry chloroform ; #end of refcif _cell_length_a 8.5238(2) _cell_length_b 16.9403(5) _cell_length_c 21.7245(6) _cell_angle_alpha 90 _cell_angle_beta 91.247(3) _cell_angle_gamma 90 _cell_volume 3136.17(16) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _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' 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' 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' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' 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' Cu -1.9646 0.5888 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C27.50 H27.50 B1.25 Cl1.25 Cu1.25 N6.25 O3.75 # Dc = 1.36 Fooo = 1520.00 Mu = 24.74 M = 642.82 # Found Formula = C24 H24 B1 Cl7 Cu1 N5 O3 # Dc = 1.59 FOOO = 1520.00 Mu = 67.78 M = 753.01 _chemical_formula_sum 'C24 H24 B1 Cl7 Cu1 N5 O3' _chemical_formula_moiety 'C24 H24 B1 Cl7 Cu1 N5 O3' _chemical_compound_source ? _chemical_formula_weight 753.01 _cell_measurement_reflns_used 17681 _cell_measurement_theta_min 2 _cell_measurement_theta_max 73 _cell_measurement_temperature 100 _exptl_crystal_description colourless _exptl_crystal_colour block _exptl_crystal_size_min 0.102 _exptl_crystal_size_mid 0.151 _exptl_crystal_size_max 0.176 _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 6.778 # Sheldrick geometric approximatio 0.36 0.50 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.35 _exptl_absorpt_correction_T_max 0.50 _diffrn_measurement_device_type 'Agilent Technologies SuperNova' _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 29658 _reflns_number_total 6197 _diffrn_reflns_av_R_equivalents 0.051 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 6197 # Theoretical number of reflections is about 12507 _diffrn_reflns_theta_min 3.309 _diffrn_reflns_theta_max 72.847 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 71.390 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 2.49 _oxford_diffrn_Wilson_scale 0.08 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.15 _refine_diff_density_max 1.20 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 6197 _refine_ls_number_restraints 15 _refine_ls_number_parameters 460 _oxford_refine_ls_R_factor_ref 0.0604 _refine_ls_wR_factor_ref 0.1444 _refine_ls_goodness_of_fit_ref 1.0016 _refine_ls_shift/su_max 0.0002370 _refine_ls_shift/su_mean 0.0000225 # The values computed from all data _oxford_reflns_number_all 6197 _refine_ls_R_factor_all 0.0604 _refine_ls_wR_factor_all 0.1444 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5739 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_gt 0.1417 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 8.21P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cu1 Cu 0.74045(5) 0.54203(3) 0.315430(19) 0.0247 1.0000 Uani . . . . . . . Cl1 Cl 0.82436(10) 0.48009(8) 0.22769(4) 0.0592 1.0000 Uani . . . . . . . Cl101 Cl 0.4309(2) 0.96566(10) 0.45822(8) 0.0406 0.5000 Uani . . . . 1 . . Cl102 Cl 0.2595(2) 0.82854(12) 0.41606(11) 0.0508 0.5000 Uani . . . . 1 . . Cl103 Cl 0.5558(2) 0.86869(10) 0.36222(7) 0.0363 0.5000 Uani . . . . 1 . . Cl104 Cl 0.3029(3) 0.92809(17) 0.45033(11) 0.0652 0.5000 Uani . . . . 2 . . Cl105 Cl 0.4029(3) 0.81223(12) 0.36278(11) 0.0607 0.5000 Uani . . . . 2 . . Cl106 Cl 0.6035(3) 0.94381(12) 0.39234(10) 0.0501 0.5000 Uani . . . . 2 . . Cl201 Cl 0.9051(2) 0.59508(12) 0.00001(11) 0.0479 0.5000 Uani . . . . 1 . . Cl202 Cl 0.9997(3) 0.54927(14) 0.12233(9) 0.0488 0.5000 Uani . . . . 1 . . Cl203 Cl 1.0961(3) 0.69956(14) 0.07464(13) 0.0642 0.5000 Uani . . . . 1 . . Cl205 Cl 0.9009(6) 0.6207(3) 0.0512(3) 0.1603 0.5000 Uani . U . . 2 . . Cl206 Cl 1.1525(3) 0.51524(12) 0.09280(11) 0.0554 0.5000 Uani . U . . 2 . . Cl207 Cl 1.1284(3) 0.67553(13) 0.13612(13) 0.0646 0.5000 Uani . U . . 2 . . O11 O 0.7856(2) 0.66038(12) 0.41964(10) 0.0242 1.0000 Uani . . . . . . . O18 O 0.5086(2) 0.64514(12) 0.39145(9) 0.0206 1.0000 Uani . . . . . . . O25 O 0.6425(2) 0.54038(11) 0.44765(8) 0.0185 1.0000 Uani . . . . . . . N7 N 0.5916(3) 0.66463(14) 0.49833(11) 0.0209 1.0000 Uani . . . . . . . N13 N 0.8066(3) 0.65738(18) 0.31404(13) 0.0337 1.0000 Uani . . . . . . . N20 N 0.5021(3) 0.54320(14) 0.32010(10) 0.0199 1.0000 Uani . . . . . . . N27 N 0.8330(3) 0.48328(15) 0.38884(11) 0.0229 1.0000 Uani . . . . . . . N300 N 0.4534(11) 0.7707(5) 0.6647(5) 0.0369 0.5000 Uani . . . . 1 . . N400 N 0.5178(10) 0.7859(6) 0.6599(4) 0.0296 0.5000 Uani . . . . 2 . . C4 C 0.5193(5) 0.7419(2) 0.60879(16) 0.0432 1.0000 Uani . . . . . . . C5 C 0.5150(4) 0.6590(2) 0.60329(14) 0.0318 1.0000 Uani . . . . . . . C6 C 0.5514(3) 0.62392(17) 0.54900(13) 0.0221 1.0000 Uani . . . . . . . C8 C 0.5931(5) 0.74433(19) 0.50267(16) 0.0357 1.0000 Uani . . . . . . . C9 C 0.5590(6) 0.7838(2) 0.55529(18) 0.0489 1.0000 Uani . . . . . . . C12 C 0.8255(3) 0.69599(19) 0.36677(15) 0.0282 1.0000 Uani . . . . . . . C14 C 0.8530(5) 0.6946(3) 0.2624(2) 0.0535 1.0000 Uani . . . . . . . C15 C 0.9204(6) 0.7672(3) 0.2620(2) 0.0645 1.0000 Uani . . . . . . . C16 C 0.9431(5) 0.8060(3) 0.3167(3) 0.0582 1.0000 Uani . . . . . . . C17 C 0.8944(4) 0.7704(2) 0.3701(2) 0.0416 1.0000 Uani . . . . . . . C19 C 0.4276(3) 0.59816(17) 0.35272(12) 0.0191 1.0000 Uani . . . . . . . C21 C 0.4150(3) 0.49786(18) 0.28072(12) 0.0224 1.0000 Uani . . . . . . . C22 C 0.2561(4) 0.5059(2) 0.27229(15) 0.0298 1.0000 Uani . . . . . . . C23 C 0.1810(4) 0.5645(2) 0.30538(16) 0.0346 1.0000 Uani . . . . . . . C24 C 0.2658(4) 0.61079(19) 0.34581(14) 0.0273 1.0000 Uani . . . . . . . C26 C 0.7655(3) 0.49081(16) 0.44328(13) 0.0211 1.0000 Uani . . . . . . . C28 C 0.9498(4) 0.4293(2) 0.38431(17) 0.0330 1.0000 Uani . . . . . . . C29 C 0.9997(4) 0.3829(2) 0.4325(2) 0.0422 1.0000 Uani . . . . . . . C30 C 0.9266(4) 0.3911(2) 0.4891(2) 0.0433 1.0000 Uani . . . . . . . C31 C 0.8079(4) 0.4459(2) 0.49461(16) 0.0317 1.0000 Uani . . . . . . . C100 C 0.3924(5) 0.9084(2) 0.38884(19) 0.0436 1.0000 Uani . . . . . . . C200 C 1.0570(10) 0.6001(5) 0.0568(4) 0.0418 0.5000 Uani . . . . 1 . . C204 C 1.0226(10) 0.5967(5) 0.1095(4) 0.0452 0.5000 Uani . U . . 2 . . C301 C 0.4556(15) 0.8564(5) 0.6727(4) 0.0493 0.5000 Uani . . . . 1 . . C302 C 0.410(2) 0.7230(8) 0.7175(7) 0.0584 0.5000 Uani . . . . 1 . . C400 C 0.5392(11) 0.8720(5) 0.6623(4) 0.0387 0.5000 Uani . . . . 2 . . C401 C 0.4739(14) 0.7437(7) 0.7154(5) 0.0402 0.5000 Uani . . . . 2 . . B10 B 0.6362(4) 0.62376(18) 0.43421(14) 0.0190 1.0000 Uani . . . . . . . H51 H 0.4868 0.6283 0.6361 0.0380 1.0000 Uiso R . . . . . . H61 H 0.5486 0.5690 0.5464 0.0273 1.0000 Uiso R . . . . . . H81 H 0.6192 0.7733 0.4675 0.0429 1.0000 Uiso R . . . . . . H91 H 0.5627 0.8385 0.5554 0.0591 1.0000 Uiso R . . . . . . H141 H 0.8361 0.6682 0.2255 0.0641 1.0000 Uiso R . . . . . . H151 H 0.9514 0.7901 0.2251 0.0771 1.0000 Uiso R . . . . . . H161 H 0.9898 0.8552 0.3177 0.0700 1.0000 Uiso R . . . . . . H171 H 0.9090 0.7949 0.4078 0.0502 1.0000 Uiso R . . . . . . H211 H 0.4669 0.4597 0.2570 0.0269 1.0000 Uiso R . . . . . . H221 H 0.2010 0.4733 0.2453 0.0355 1.0000 Uiso R . . . . . . H231 H 0.0746 0.5724 0.2997 0.0415 1.0000 Uiso R . . . . . . H241 H 0.2183 0.6498 0.3688 0.0332 1.0000 Uiso R . . . . . . H281 H 0.9953 0.4237 0.3463 0.0388 1.0000 Uiso R . . . . . . H291 H 1.0812 0.3466 0.4273 0.0511 1.0000 Uiso R . . . . . . H301 H 0.9576 0.3605 0.5232 0.0518 1.0000 Uiso R . . . . . . H311 H 0.7571 0.4526 0.5320 0.0381 1.0000 Uiso R . . . . . . H2001 H 1.1512 0.5744 0.0414 0.0501 0.5000 Uiso R . . . 1 . . H2041 H 0.9565 0.5802 0.1438 0.0544 0.5000 Uiso R . . . 2 . . H3011 H 0.4206 0.8691 0.7131 0.0740 0.5000 Uiso R . . . 1 . . H3013 H 0.3871 0.8806 0.6425 0.0741 0.5000 Uiso R . . . 1 . . H3012 H 0.5604 0.8757 0.6677 0.0740 0.5000 Uiso R . . . 1 . . H3021 H 0.5008 0.6954 0.7336 0.0879 0.5000 Uiso R . . . 1 . . H3022 H 0.3699 0.7569 0.7488 0.0878 0.5000 Uiso R . . . 1 . . H3023 H 0.3307 0.6856 0.7059 0.0878 0.5000 Uiso R . . . 1 . . H4002 H 0.5380 0.8884 0.7047 0.0580 0.5000 Uiso R . . . 2 . . H4001 H 0.6374 0.8861 0.6444 0.0579 0.5000 Uiso R . . . 2 . . H4003 H 0.4549 0.8968 0.6396 0.0579 0.5000 Uiso R . . . 2 . . H4012 H 0.5553 0.7072 0.7279 0.0609 0.5000 Uiso R . . . 2 . . H4011 H 0.4588 0.7802 0.7483 0.0609 0.5000 Uiso R . . . 2 . . H4013 H 0.3776 0.7151 0.7085 0.0610 0.5000 Uiso R . . . 2 . . H1001 H 0.3396 0.9406 0.3574 0.0519 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 Cu1 0.0183(2) 0.0362(3) 0.0197(2) -0.00189(17) 0.00114(16) 0.00337(17) Cl1 0.0259(4) 0.1149(9) 0.0366(5) -0.0431(5) -0.0063(3) 0.0172(5) Cl101 0.0627(11) 0.0294(8) 0.0297(8) -0.0045(6) 0.0006(7) 0.0013(7) Cl102 0.0324(8) 0.0456(10) 0.0742(13) 0.0035(9) -0.0009(8) -0.0102(7) Cl103 0.0410(8) 0.0433(9) 0.0247(7) 0.0068(6) 0.0062(6) 0.0113(7) Cl104 0.0640(14) 0.0851(17) 0.0467(11) -0.0212(11) 0.0061(10) 0.0082(12) Cl105 0.0794(15) 0.0345(10) 0.0676(14) -0.0188(9) -0.0148(12) 0.0081(9) Cl106 0.0571(11) 0.0453(10) 0.0475(10) 0.0035(8) -0.0077(9) 0.0034(9) Cl201 0.0406(10) 0.0417(10) 0.0615(12) 0.0115(9) -0.0007(9) 0.0064(8) Cl202 0.0550(11) 0.0556(13) 0.0361(9) -0.0020(9) 0.0051(8) 0.0044(9) Cl203 0.0701(14) 0.0444(11) 0.0786(16) -0.0120(11) 0.0129(12) -0.0093(10) Cl205 0.136(4) 0.128(4) 0.211(6) 0.083(4) -0.126(4) -0.038(3) Cl206 0.0641(13) 0.0434(10) 0.0600(12) -0.0038(9) 0.0297(10) 0.0057(9) Cl207 0.0671(14) 0.0420(11) 0.0855(17) -0.0042(11) 0.0163(12) -0.0022(10) O11 0.0186(9) 0.0253(10) 0.0287(11) 0.0088(8) -0.0020(8) -0.0020(8) O18 0.0208(9) 0.0232(10) 0.0176(9) -0.0004(7) -0.0021(7) 0.0042(8) O25 0.0205(9) 0.0181(9) 0.0169(9) 0.0001(7) 0.0012(7) 0.0007(7) N7 0.0268(12) 0.0182(11) 0.0175(11) 0.0001(9) -0.0038(9) 0.0010(9) N13 0.0282(13) 0.0423(16) 0.0310(14) 0.0152(12) 0.0069(11) 0.0003(12) N20 0.0190(11) 0.0253(12) 0.0154(11) 0.0027(9) -0.0006(9) -0.0006(9) N27 0.0190(11) 0.0226(12) 0.0270(12) -0.0026(10) -0.0021(9) 0.0024(9) N300 0.056(6) 0.025(4) 0.030(4) -0.005(3) 0.001(5) 0.006(4) N400 0.040(5) 0.030(4) 0.019(3) -0.010(3) 0.002(3) 0.000(3) C4 0.071(3) 0.0347(19) 0.0233(16) -0.0095(14) -0.0128(16) 0.0211(18) C5 0.0453(19) 0.0300(16) 0.0199(14) -0.0013(12) -0.0009(13) 0.0102(14) C6 0.0259(14) 0.0202(13) 0.0203(13) 0.0001(11) 0.0003(11) 0.0005(11) C8 0.061(2) 0.0179(14) 0.0282(16) 0.0027(12) -0.0060(15) 0.0017(14) C9 0.089(3) 0.0213(16) 0.0354(19) -0.0064(14) -0.013(2) 0.0125(18) C12 0.0184(13) 0.0279(15) 0.0384(17) 0.0150(13) 0.0041(12) 0.0040(11) C14 0.050(2) 0.069(3) 0.042(2) 0.026(2) 0.0115(18) -0.006(2) C15 0.058(3) 0.070(3) 0.066(3) 0.046(3) 0.019(2) -0.001(2) C16 0.045(2) 0.036(2) 0.094(4) 0.036(2) 0.021(2) 0.0020(17) C17 0.0328(17) 0.0248(16) 0.068(3) 0.0122(16) 0.0138(17) 0.0023(13) C19 0.0183(13) 0.0252(14) 0.0140(12) 0.0045(10) 0.0007(10) 0.0022(10) C21 0.0257(14) 0.0265(14) 0.0152(12) 0.0009(11) 0.0011(10) -0.0021(11) C22 0.0255(15) 0.0364(17) 0.0273(15) -0.0002(13) -0.0039(12) -0.0070(13) C23 0.0173(14) 0.049(2) 0.0371(17) 0.0028(15) -0.0032(12) 0.0003(13) C24 0.0216(14) 0.0343(16) 0.0260(14) 0.0023(12) 0.0017(11) 0.0049(12) C26 0.0191(13) 0.0191(13) 0.0249(14) 0.0000(11) -0.0049(10) -0.0014(10) C28 0.0207(14) 0.0344(17) 0.0437(19) -0.0076(14) -0.0013(13) 0.0062(13) C29 0.0259(16) 0.0323(18) 0.068(3) 0.0023(17) -0.0065(16) 0.0113(14) C30 0.0350(18) 0.0378(19) 0.056(2) 0.0170(17) -0.0147(17) 0.0078(15) C31 0.0299(16) 0.0333(17) 0.0314(16) 0.0087(13) -0.0074(13) -0.0005(13) C100 0.052(2) 0.0321(18) 0.046(2) -0.0080(15) -0.0200(17) 0.0132(16) C200 0.046(4) 0.040(4) 0.041(4) 0.008(3) 0.010(3) 0.001(3) C204 0.052(4) 0.019(3) 0.065(4) 0.024(3) 0.019(3) -0.004(3) C301 0.082(8) 0.027(4) 0.039(5) -0.005(3) 0.009(5) 0.005(5) C302 0.105(12) 0.040(7) 0.031(5) -0.005(4) 0.023(7) 0.007(6) C400 0.052(5) 0.032(4) 0.032(4) -0.017(3) 0.004(4) -0.002(4) C401 0.062(7) 0.041(6) 0.018(4) -0.008(4) 0.012(4) 0.002(4) B10 0.0206(14) 0.0190(14) 0.0173(14) 0.0014(11) -0.0015(11) -0.0011(11) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.60(5) 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 Cu1 . Cl1 . 2.3033(9) yes Cu1 . N13 . 2.034(3) yes Cu1 . N20 . 2.036(2) yes Cu1 . N27 . 2.025(2) yes Cl101 . Cl101 2_676 2.438(3) yes Cl101 . C100 . 1.816(4) yes Cl102 . C100 . 1.869(5) yes Cl103 . C100 . 1.662(4) yes Cl104 . C100 . 1.588(5) yes Cl105 . C100 . 1.728(4) yes Cl106 . Cl206 3_755 2.421(3) yes Cl106 . C100 . 1.897(5) yes Cl201 . C200 . 1.771(9) yes Cl202 . C200 . 1.743(8) yes Cl203 . C200 . 1.758(8) yes Cl205 . C204 . 1.671(9) yes Cl206 . C204 . 1.811(8) yes Cl207 . C204 . 1.705(9) yes O11 . C12 . 1.348(4) yes O11 . B10 . 1.457(4) yes O18 . C19 . 1.339(3) yes O18 . B10 . 1.461(3) yes O25 . C26 . 1.348(3) yes O25 . B10 . 1.443(4) yes N7 . C6 . 1.349(4) yes N7 . C8 . 1.354(4) yes N7 . B10 . 1.609(4) yes N13 . C12 . 1.326(5) yes N13 . C14 . 1.354(5) yes N20 . C19 . 1.338(4) yes N20 . C21 . 1.358(4) yes N27 . C26 . 1.333(4) yes N27 . C28 . 1.357(4) yes N300 . C4 . 1.434(11) yes N300 . C301 . 1.462(12) yes N300 . C302 . 1.458(15) yes N400 . C4 . 1.336(9) yes N400 . C400 . 1.471(12) yes N400 . C401 . 1.457(13) yes C4 . C5 . 1.409(5) yes C4 . C9 . 1.409(6) yes C5 . C6 . 1.363(4) yes C5 . H51 . 0.920 no C6 . H61 . 0.932 no C8 . C9 . 1.361(5) yes C8 . H81 . 0.938 no C9 . H91 . 0.927 no C12 . C17 . 1.391(5) yes C14 . C15 . 1.357(7) yes C14 . H141 . 0.926 no C15 . C16 . 1.369(8) yes C15 . H151 . 0.934 no C16 . C17 . 1.380(6) yes C16 . H161 . 0.924 no C17 . H171 . 0.924 no C19 . C24 . 1.401(4) yes C21 . C22 . 1.370(4) yes C21 . H211 . 0.943 no C22 . C23 . 1.390(5) yes C22 . H221 . 0.926 no C23 . C24 . 1.371(5) yes C23 . H231 . 0.922 no C24 . H241 . 0.927 no C26 . C31 . 1.392(4) yes C28 . C29 . 1.370(5) yes C28 . H281 . 0.925 no C29 . C30 . 1.397(6) yes C29 . H291 . 0.936 no C30 . C31 . 1.380(5) yes C30 . H301 . 0.937 no C31 . H311 . 0.936 no C100 . H1001 . 0.976 no C200 . H2001 . 0.979 no C204 . H2041 . 0.984 no C301 . H3011 . 0.959 no C301 . H3013 . 0.960 no C301 . H3012 . 0.960 no C302 . H3021 . 0.964 no C302 . H3022 . 0.958 no C302 . H3023 . 0.956 no C400 . H4002 . 0.962 no C400 . H4001 . 0.960 no C400 . H4003 . 0.960 no C401 . H4012 . 0.964 no C401 . H4011 . 0.956 no C401 . H4013 . 0.963 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 Cl1 . Cu1 . N13 . 109.52(9) yes Cl1 . Cu1 . N20 . 111.94(7) yes N13 . Cu1 . N20 . 105.58(10) yes Cl1 . Cu1 . N27 . 107.77(8) yes N13 . Cu1 . N27 . 112.36(11) yes N20 . Cu1 . N27 . 109.72(10) yes Cl101 2_676 Cl101 . C100 . 161.6(2) yes Cl206 3_755 Cl106 . C100 . 167.04(17) yes Cl106 3_745 Cl206 . C204 . 151.8(3) yes C12 . O11 . B10 . 127.9(2) yes C19 . O18 . B10 . 128.2(2) yes C26 . O25 . B10 . 128.4(2) yes C6 . N7 . C8 . 117.1(3) yes C6 . N7 . B10 . 123.7(2) yes C8 . N7 . B10 . 119.2(2) yes Cu1 . N13 . C12 . 119.3(2) yes Cu1 . N13 . C14 . 123.1(3) yes C12 . N13 . C14 . 117.0(3) yes Cu1 . N20 . C19 . 121.21(19) yes Cu1 . N20 . C21 . 119.69(19) yes C19 . N20 . C21 . 117.9(2) yes Cu1 . N27 . C26 . 118.93(19) yes Cu1 . N27 . C28 . 123.2(2) yes C26 . N27 . C28 . 117.4(3) yes C4 . N300 . C301 . 115.7(8) yes C4 . N300 . C302 . 126.1(9) yes C301 . N300 . C302 . 117.3(9) yes C4 . N400 . C400 . 125.4(8) yes C4 . N400 . C401 . 114.9(8) yes C400 . N400 . C401 . 119.3(8) yes N300 . C4 . C5 . 113.6(5) yes N300 . C4 . C9 . 129.2(5) yes C5 . C4 . C9 . 115.9(3) yes C4 . C5 . C6 . 120.2(3) yes C4 . C5 . H51 . 120.3 no C6 . C5 . H51 . 119.5 no C5 . C6 . N7 . 123.3(3) yes C5 . C6 . H61 . 118.8 no N7 . C6 . H61 . 117.9 no N7 . C8 . C9 . 123.1(3) yes N7 . C8 . H81 . 117.9 no C9 . C8 . H81 . 119.0 no C4 . C9 . C8 . 120.4(3) yes C4 . C9 . H91 . 120.7 no C8 . C9 . H91 . 119.0 no O11 . C12 . N13 . 119.2(3) yes O11 . C12 . C17 . 118.4(3) yes N13 . C12 . C17 . 122.3(3) yes N13 . C14 . C15 . 124.0(5) yes N13 . C14 . H141 . 116.6 no C15 . C14 . H141 . 119.4 no C14 . C15 . C16 . 118.8(4) yes C14 . C15 . H151 . 120.7 no C16 . C15 . H151 . 120.5 no C15 . C16 . C17 . 118.7(4) yes C15 . C16 . H161 . 120.4 no C17 . C16 . H161 . 120.8 no C12 . C17 . C16 . 119.1(4) yes C12 . C17 . H171 . 120.1 no C16 . C17 . H171 . 120.8 no O18 . C19 . N20 . 120.2(2) yes O18 . C19 . C24 . 118.0(3) yes N20 . C19 . C24 . 121.8(3) yes N20 . C21 . C22 . 123.6(3) yes N20 . C21 . H211 . 118.4 no C22 . C21 . H211 . 118.0 no C21 . C22 . C23 . 117.9(3) yes C21 . C22 . H221 . 120.7 no C23 . C22 . H221 . 121.4 no C22 . C23 . C24 . 119.8(3) yes C22 . C23 . H231 . 119.7 no C24 . C23 . H231 . 120.4 no C19 . C24 . C23 . 119.0(3) yes C19 . C24 . H241 . 119.4 no C23 . C24 . H241 . 121.5 no O25 . C26 . N27 . 118.3(2) yes O25 . C26 . C31 . 118.3(3) yes N27 . C26 . C31 . 123.3(3) yes N27 . C28 . C29 . 123.2(3) yes N27 . C28 . H281 . 117.1 no C29 . C28 . H281 . 119.7 no C28 . C29 . C30 . 118.6(3) yes C28 . C29 . H291 . 120.2 no C30 . C29 . H291 . 121.2 no C29 . C30 . C31 . 119.0(3) yes C29 . C30 . H301 . 121.2 no C31 . C30 . H301 . 119.8 no C26 . C31 . C30 . 118.5(3) yes C26 . C31 . H311 . 120.7 no C30 . C31 . H311 . 120.8 no Cl102 . C100 . Cl101 . 102.9(2) yes Cl102 . C100 . Cl103 . 109.6(2) yes Cl101 . C100 . Cl103 . 111.5(2) yes Cl102 . C100 . H1001 . 110.6 no Cl101 . C100 . H1001 . 110.8 no Cl103 . C100 . H1001 . 111.1 no Cl201 . C200 . Cl203 . 109.4(4) yes Cl201 . C200 . Cl202 . 109.4(4) yes Cl203 . C200 . Cl202 . 110.4(5) yes Cl201 . C200 . H2001 . 109.4 no Cl203 . C200 . H2001 . 110.4 no Cl202 . C200 . H2001 . 107.8 no Cl206 . C204 . Cl207 . 110.1(5) yes Cl206 . C204 . Cl205 . 113.9(6) yes Cl207 . C204 . Cl205 . 112.5(5) yes Cl206 . C204 . H2041 . 107.3 no Cl207 . C204 . H2041 . 105.9 no Cl205 . C204 . H2041 . 106.7 no N300 . C301 . H3011 . 109.2 no N300 . C301 . H3013 . 109.7 no H3011 . C301 . H3013 . 109.5 no N300 . C301 . H3012 . 109.6 no H3011 . C301 . H3012 . 109.6 no H3013 . C301 . H3012 . 109.3 no N300 . C302 . H3021 . 109.9 no N300 . C302 . H3022 . 109.2 no H3021 . C302 . H3022 . 109.2 no N300 . C302 . H3023 . 110.4 no H3021 . C302 . H3023 . 109.4 no H3022 . C302 . H3023 . 108.8 no N400 . C400 . H4002 . 108.5 no N400 . C400 . H4001 . 109.9 no H4002 . C400 . H4001 . 110.0 no N400 . C400 . H4003 . 109.0 no H4002 . C400 . H4003 . 110.0 no H4001 . C400 . H4003 . 109.4 no N400 . C401 . H4012 . 110.6 no N400 . C401 . H4011 . 110.1 no H4012 . C401 . H4011 . 108.2 no N400 . C401 . H4013 . 110.6 no H4012 . C401 . H4013 . 109.0 no H4011 . C401 . H4013 . 108.2 no N7 . B10 . O18 . 104.9(2) yes N7 . B10 . O11 . 103.2(2) yes O18 . B10 . O11 . 113.5(2) yes N7 . B10 . O25 . 104.7(2) yes O18 . B10 . O25 . 113.3(2) yes O11 . B10 . O25 . 115.6(2) yes