# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_yb5 _database_code_depnum_ccdc_archive 'CCDC 883200' #TrackingRef 'yb5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 Cu N7 O, B F4' _chemical_formula_sum 'C6 H10 B Cu F4 N7 O' _chemical_formula_weight 346.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M ' P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.566(2) _cell_length_b 10.457(3) _cell_length_c 17.386(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1193.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3. _cell_measurement_theta_max 24.4 _exptl_crystal_description parallelipiped _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.928 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.889 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '60 images, \D\F 3\%' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4859 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 24.39 _reflns_number_total 1848 _reflns_number_gt 1705 _reflns_threshold_expression >2sigma(I) _computing_data_collection MAR _computing_cell_refinement MAR _computing_data_reduction MARHKL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The data were not corrected for absorption but the collection mode take at least partially the absorption phenomena into account (see the total number of images and collected reflexions vs the number of independent reflexions). The H atoms were refined with a common isotropic temperature parameter. (U~eq~ = 0.015 \%A^2^). The other absolute configuration has also been refined but the R indices are not better. The option "twin" has been used for perfect racemic twinning 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. ; _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^)+(0.0000P)^2^+3.4233P] 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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0124(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _chemical_absolute_configuration . _refine_ls_number_reflns 1848 _refine_ls_number_parameters 213 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1013 _refine_ls_wR_factor_gt 0.0986 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.059 _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 Cu1 Cu 0.20252(8) 0.74064(5) 0.49943(4) 0.0171(2) Uani 1 1 d . . . N1 N 0.0518(7) 0.7243(5) 0.3988(2) 0.0197(10) Uani 1 1 d . . . N2 N 0.3471(7) 0.7549(4) 0.6005(2) 0.0179(10) Uani 1 1 d . . . C3 C 0.2840(9) 0.7574(6) 0.6713(3) 0.0181(11) Uani 1 1 d . . . N4 N -0.0582(7) 0.7212(4) 0.2812(2) 0.0189(10) Uani 1 1 d . . . C5 C 0.1061(9) 0.7082(5) 0.3269(3) 0.0174(12) Uani 1 1 d . . . C6 C -0.0689(11) 0.7120(6) 0.1969(3) 0.0229(14) Uani 1 1 d . . . C7 C -0.0033(10) 0.5833(6) 0.1672(3) 0.0227(14) Uani 1 1 d . . . C8 C -0.0326(10) 0.5751(6) 0.0809(3) 0.0222(13) Uani 1 1 d . . . N9 N 0.2483(8) 1.0707(4) 0.4416(2) 0.0209(11) Uani 1 1 d . . . N10 N 0.3415(8) 0.9587(4) 0.4540(3) 0.0254(11) Uani 1 1 d . . . N11 N 0.0333(8) 0.5167(5) 0.5298(3) 0.0267(11) Uani 1 1 d . . . N12 N 0.5627(9) 1.1144(5) 0.4683(3) 0.0302(13) Uani 1 1 d . . . C13 C 0.3862(10) 1.1655(5) 0.4500(3) 0.0247(13) Uani 1 1 d . . . O1 O 0.4580(6) 0.6910(4) 0.4560(2) 0.0209(9) Uani 1 1 d D . . B1 B 0.4252(12) 0.9344(7) 0.1808(4) 0.0253(16) Uani 1 1 d . . . F1 F 0.4924(8) 1.0198(4) 0.2346(2) 0.0488(11) Uani 1 1 d . . . F2 F 0.5421(7) 0.9436(4) 0.1148(2) 0.0476(12) Uani 1 1 d . . . F3 F 0.4345(6) 0.8084(3) 0.20903(19) 0.0311(9) Uani 1 1 d . . . F4 F 0.2236(6) 0.9621(3) 0.1620(3) 0.0454(11) Uani 1 1 d . . . H1 H 0.478(9) 0.620(3) 0.440(3) 0.015(5) Uiso 1 1 d D . . H3 H 0.170(10) 0.748(6) 0.684(3) 0.015(5) Uiso 1 1 d . . . H5 H 0.244(10) 0.697(5) 0.312(3) 0.015(5) Uiso 1 1 d . . . H6A H -0.198(9) 0.738(5) 0.180(3) 0.015(5) Uiso 1 1 d . . . H6B H 0.004(9) 0.773(6) 0.180(3) 0.015(5) Uiso 1 1 d . . . H7A H -0.080(9) 0.515(5) 0.194(3) 0.015(5) Uiso 1 1 d . . . H7B H 0.158(10) 0.550(5) 0.174(3) 0.015(5) Uiso 1 1 d . . . H8A H 0.012(9) 0.502(6) 0.060(3) 0.015(5) Uiso 1 1 d . . . H8B H 0.034(9) 0.654(5) 0.050(3) 0.015(5) Uiso 1 1 d . . . H13 H 0.345(8) 1.258(5) 0.445(3) 0.015(5) Uiso 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 Cu1 0.0149(4) 0.0230(3) 0.0134(3) -0.0023(3) -0.0009(3) 0.0008(2) N1 0.019(3) 0.024(2) 0.016(2) -0.0019(18) 0.0000(18) -0.001(2) N2 0.014(3) 0.017(2) 0.023(2) 0.0015(19) 0.0009(17) -0.001(2) C3 0.018(3) 0.023(3) 0.013(2) 0.000(2) 0.003(2) 0.005(3) N4 0.021(3) 0.024(2) 0.012(2) 0.0013(18) 0.0007(18) -0.002(2) C5 0.012(3) 0.023(3) 0.017(3) -0.003(2) -0.001(2) -0.001(2) C6 0.027(4) 0.026(3) 0.015(3) 0.005(2) -0.002(3) 0.002(3) C7 0.030(4) 0.021(3) 0.017(3) -0.001(2) -0.003(2) 0.001(3) C8 0.020(4) 0.027(3) 0.019(3) -0.007(2) 0.000(2) -0.001(3) N9 0.026(3) 0.023(2) 0.013(2) 0.0021(18) -0.001(2) 0.000(2) N10 0.024(3) 0.022(2) 0.030(3) 0.005(2) -0.002(2) 0.008(2) N11 0.025(3) 0.024(3) 0.031(3) 0.003(2) 0.002(2) 0.001(2) N12 0.033(4) 0.028(3) 0.029(3) 0.003(2) -0.006(3) -0.005(2) C13 0.028(4) 0.022(3) 0.024(3) -0.001(2) -0.005(3) -0.001(3) O1 0.025(2) 0.0164(19) 0.022(2) -0.0043(16) 0.0020(18) 0.0048(16) B1 0.027(5) 0.022(3) 0.028(4) 0.001(3) 0.004(3) 0.001(3) F1 0.061(3) 0.043(2) 0.042(2) -0.0118(18) -0.007(2) -0.013(2) F2 0.072(3) 0.027(2) 0.044(2) 0.0129(17) 0.033(2) 0.012(2) F3 0.035(2) 0.0240(18) 0.0337(19) 0.0118(15) 0.0042(18) 0.0023(16) F4 0.032(3) 0.030(2) 0.074(3) 0.0048(19) -0.010(2) 0.0043(18) _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 Cu1 O1 1.912(4) . ? Cu1 O1 1.921(4) 3_466 ? Cu1 N2 2.002(4) . ? Cu1 N1 2.018(4) . ? N1 C5 1.310(7) . ? N1 N2 1.361(6) 3_466 ? N2 C3 1.300(7) . ? N2 N1 1.361(6) 3_566 ? C3 N4 1.344(7) 3_566 ? C3 H3 0.79(6) . ? N4 C3 1.344(7) 3_466 ? N4 C5 1.347(7) . ? N4 C6 1.470(7) . ? C5 H5 0.95(6) . ? C6 C7 1.504(9) . ? C6 H6A 0.93(6) . ? C6 H6B 0.84(6) . ? C7 C8 1.515(8) . ? C7 H7A 0.99(6) . ? C7 H7B 1.12(6) . ? C8 N9 1.470(8) 4_545 ? C8 H8A 0.90(6) . ? C8 H8B 1.07(6) . ? N9 N10 1.339(7) . ? N9 C13 1.351(8) . ? N9 C8 1.470(8) 4 ? N10 N11 1.316(7) 3_566 ? N11 N10 1.316(7) 3_466 ? N11 N12 1.385(7) 3_466 ? N12 C13 1.315(9) . ? N12 N11 1.385(7) 3_566 ? C13 H13 1.01(6) . ? O1 Cu1 1.921(4) 3_566 ? O1 H1 0.81(3) . ? B1 F1 1.366(8) . ? B1 F2 1.383(8) . ? B1 F4 1.394(9) . ? B1 F3 1.408(8) . ? 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 O1 Cu1 O1 173.73(10) . 3_466 ? O1 Cu1 N2 87.16(17) . . ? O1 Cu1 N2 90.84(17) 3_466 . ? O1 Cu1 N1 93.72(17) . . ? O1 Cu1 N1 88.37(17) 3_466 . ? N2 Cu1 N1 178.74(19) . . ? C5 N1 N2 107.4(4) . 3_466 ? C5 N1 Cu1 134.8(4) . . ? N2 N1 Cu1 117.5(3) 3_466 . ? C3 N2 N1 107.6(4) . 3_566 ? C3 N2 Cu1 133.0(4) . . ? N1 N2 Cu1 119.2(3) 3_566 . ? N2 C3 N4 109.9(5) . 3_566 ? N2 C3 H3 125(4) . . ? N4 C3 H3 125(4) 3_566 . ? C3 N4 C5 105.7(4) 3_466 . ? C3 N4 C6 125.9(5) 3_466 . ? C5 N4 C6 128.3(5) . . ? N1 C5 N4 109.4(5) . . ? N1 C5 H5 122(3) . . ? N4 C5 H5 128(3) . . ? N4 C6 C7 112.8(5) . . ? N4 C6 H6A 109(3) . . ? C7 C6 H6A 114(4) . . ? N4 C6 H6B 105(4) . . ? C7 C6 H6B 113(4) . . ? H6A C6 H6B 101(5) . . ? C6 C7 C8 110.7(5) . . ? C6 C7 H7A 110(3) . . ? C8 C7 H7A 111(3) . . ? C6 C7 H7B 121(3) . . ? C8 C7 H7B 102(3) . . ? H7A C7 H7B 102(4) . . ? N9 C8 C7 112.9(5) 4_545 . ? N9 C8 H8A 100(4) 4_545 . ? C7 C8 H8A 114(4) . . ? N9 C8 H8B 107(3) 4_545 . ? C7 C8 H8B 113(3) . . ? H8A C8 H8B 109(4) . . ? N10 N9 C13 108.6(5) . . ? N10 N9 C8 120.7(5) . 4 ? C13 N9 C8 130.7(5) . 4 ? N11 N10 N9 107.5(5) 3_566 . ? N10 N11 N12 108.8(5) 3_466 3_466 ? C13 N12 N11 106.6(5) . 3_566 ? N12 C13 N9 108.6(5) . . ? N12 C13 H13 130(3) . . ? N9 C13 H13 121(3) . . ? Cu1 O1 Cu1 118.23(19) . 3_566 ? Cu1 O1 H1 122(4) . . ? Cu1 O1 H1 111(4) 3_566 . ? F1 B1 F2 110.0(6) . . ? F1 B1 F4 109.4(5) . . ? F2 B1 F4 108.5(5) . . ? F1 B1 F3 111.1(5) . . ? F2 B1 F3 109.3(5) . . ? F4 B1 F3 108.5(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 N1 C5 -10.6(6) . . . . ? O1 Cu1 N1 C5 163.4(6) 3_466 . . . ? O1 Cu1 N1 N2 176.9(4) . . . 3_466 ? O1 Cu1 N1 N2 -9.0(4) 3_466 . . 3_466 ? O1 Cu1 N2 C3 -161.6(5) . . . . ? O1 Cu1 N2 C3 24.4(5) 3_466 . . . ? O1 Cu1 N2 N1 24.2(4) . . . 3_566 ? O1 Cu1 N2 N1 -149.8(4) 3_466 . . 3_566 ? N1 N2 C3 N4 -0.3(6) 3_566 . . 3_566 ? Cu1 N2 C3 N4 -175.0(4) . . . 3_566 ? N2 N1 C5 N4 1.4(6) 3_466 . . . ? Cu1 N1 C5 N4 -171.6(4) . . . . ? C3 N4 C5 N1 -1.6(6) 3_466 . . . ? C6 N4 C5 N1 179.6(5) . . . . ? C3 N4 C6 C7 -118.3(7) 3_466 . . . ? C5 N4 C6 C7 60.4(8) . . . . ? N4 C6 C7 C8 175.6(5) . . . . ? C6 C7 C8 N9 -70.1(7) . . . 4_545 ? C13 N9 N10 N11 0.4(6) . . . 3_566 ? C8 N9 N10 N11 177.6(4) 4 . . 3_566 ? N11 N12 C13 N9 0.9(6) 3_566 . . . ? N10 N9 C13 N12 -0.8(6) . . . . ? C8 N9 C13 N12 -177.6(5) 4 . . . ? N2 Cu1 O1 Cu1 -31.0(2) . . . 3_566 ? N1 Cu1 O1 Cu1 149.9(2) . . . 3_566 ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 24.39 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.738 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.093