# Electronic Supplementary Material (ESI) for Chemical Communications # 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_wa1144 _database_code_depnum_ccdc_archive 'CCDC 873313' #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 B2 N2' _chemical_formula_sum 'C18 H22 B2 N2' _chemical_formula_weight 288.00 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 12.4867(7) _cell_length_b 8.0814(6) _cell_length_c 16.3838(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1653.29(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10936 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.066 _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 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 26385 _diffrn_reflns_av_R_equivalents 0.0660 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.66 _reflns_number_total 1548 _reflns_number_gt 1143 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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. ; _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^)+(0.0528P)^2^] 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 1548 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 N1 N 0.44051(11) 0.43429(16) 0.14825(8) 0.0297(3) Uani 1 1 d . . . B1 B 0.46021(13) 0.5557(2) 0.20685(11) 0.0240(4) Uani 1 1 d . . . C1 C 0.42254(12) 0.74602(19) 0.19228(9) 0.0238(3) Uani 1 1 d . . . H1 H 0.3656 0.7572 0.1497 0.029 Uiso 1 1 calc R . . C2 C 0.36999(16) 0.4548(2) 0.07766(12) 0.0435(5) Uani 1 1 d . . . H2A H 0.3368 0.5646 0.0795 0.065 Uiso 1 1 calc R . . H2B H 0.3141 0.3697 0.0789 0.065 Uiso 1 1 calc R . . H2C H 0.4119 0.4438 0.0274 0.065 Uiso 1 1 calc R . . C3 C 0.49114(16) 0.2711(2) 0.14742(13) 0.0438(5) Uani 1 1 d . . . H3A H 0.5380 0.2600 0.1951 0.066 Uiso 1 1 calc R . . H3B H 0.5335 0.2587 0.0975 0.066 Uiso 1 1 calc R . . H3C H 0.4358 0.1852 0.1492 0.066 Uiso 1 1 calc R . . C11 C 0.52936(12) 0.81847(17) 0.16623(10) 0.0240(4) Uani 1 1 d . . . C12 C 0.60911(12) 0.82009(18) 0.22649(10) 0.0242(4) Uani 1 1 d . . . C13 C 0.70942(13) 0.8848(2) 0.20830(11) 0.0321(4) Uani 1 1 d . . . H13 H 0.7633 0.8878 0.2492 0.039 Uiso 1 1 calc R . . C14 C 0.73154(14) 0.9452(2) 0.13074(12) 0.0386(5) Uani 1 1 d . . . H14 H 0.7998 0.9912 0.1189 0.046 Uiso 1 1 calc R . . C15 C 0.65391(15) 0.9382(2) 0.07090(11) 0.0371(4) Uani 1 1 d . . . H15 H 0.6696 0.9769 0.0175 0.045 Uiso 1 1 calc R . . C16 C 0.55302(14) 0.8750(2) 0.08829(10) 0.0308(4) Uani 1 1 d . . . H16 H 0.5001 0.8705 0.0467 0.037 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 N1 0.0296(7) 0.0263(7) 0.0331(8) -0.0061(6) -0.0041(6) 0.0005(6) B1 0.0194(8) 0.0241(9) 0.0283(9) 0.0006(7) 0.0037(7) -0.0031(7) C1 0.0225(7) 0.0265(7) 0.0224(8) -0.0004(7) -0.0053(6) 0.0018(6) C2 0.0464(11) 0.0454(11) 0.0388(11) -0.0118(9) -0.0131(9) -0.0054(9) C3 0.0492(11) 0.0291(9) 0.0532(13) -0.0132(8) -0.0052(9) 0.0050(8) C11 0.0278(8) 0.0171(7) 0.0271(9) -0.0013(6) 0.0006(7) 0.0031(6) C12 0.0262(8) 0.0192(7) 0.0273(9) -0.0018(6) 0.0005(7) 0.0010(6) C13 0.0263(8) 0.0320(9) 0.0380(11) -0.0009(8) 0.0001(7) -0.0030(7) C14 0.0328(9) 0.0358(9) 0.0471(11) 0.0037(9) 0.0117(8) -0.0048(7) C15 0.0431(10) 0.0369(10) 0.0313(10) 0.0067(8) 0.0137(8) 0.0035(8) C16 0.0378(10) 0.0283(8) 0.0263(9) 0.0013(7) 0.0011(7) 0.0055(7) _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 N1 B1 1.394(2) . ? N1 C3 1.463(2) . ? N1 C2 1.463(2) . ? B1 C1 1.626(2) . ? B1 B1 1.728(4) 4_655 ? C1 C12 1.512(2) 4_655 ? C1 C11 1.518(2) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C11 C16 1.388(2) . ? C11 C12 1.402(2) . ? C12 C13 1.390(2) . ? C12 C1 1.512(2) 4_655 ? C13 C14 1.389(3) . ? C13 H13 0.9500 . ? C14 C15 1.380(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(3) . ? C15 H15 0.9500 . ? C16 H16 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 B1 N1 C3 124.36(14) . . ? B1 N1 C2 124.80(14) . . ? C3 N1 C2 110.80(14) . . ? N1 B1 C1 120.89(14) . . ? N1 B1 B1 131.66(10) . 4_655 ? C1 B1 B1 106.64(9) . 4_655 ? C12 C1 C11 108.94(12) 4_655 . ? C12 C1 B1 108.72(12) 4_655 . ? C11 C1 B1 98.74(11) . . ? C12 C1 H1 113.1 4_655 . ? C11 C1 H1 113.1 . . ? B1 C1 H1 113.1 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C16 C11 C12 119.57(15) . . ? C16 C11 C1 124.95(14) . . ? C12 C11 C1 115.44(14) . . ? C13 C12 C11 119.50(15) . . ? C13 C12 C1 124.99(14) . 4_655 ? C11 C12 C1 115.50(13) . 4_655 ? C14 C13 C12 120.51(16) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 119.73(16) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.43(16) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 120.19(16) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? 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 C3 N1 B1 C1 165.84(15) . . . . ? C2 N1 B1 C1 -11.6(2) . . . . ? C3 N1 B1 B1 -2.4(3) . . . 4_655 ? C2 N1 B1 B1 -179.83(19) . . . 4_655 ? N1 B1 C1 C12 145.99(14) . . . 4_655 ? B1 B1 C1 C12 -43.17(18) 4_655 . . 4_655 ? N1 B1 C1 C11 -100.50(16) . . . . ? B1 B1 C1 C11 70.34(17) 4_655 . . . ? C12 C1 C11 C16 -135.09(15) 4_655 . . . ? B1 C1 C11 C16 111.57(16) . . . . ? C12 C1 C11 C12 47.48(15) 4_655 . . . ? B1 C1 C11 C12 -65.85(15) . . . . ? C16 C11 C12 C13 2.7(2) . . . . ? C1 C11 C12 C13 -179.72(14) . . . . ? C16 C11 C12 C1 -176.28(13) . . . 4_655 ? C1 C11 C12 C1 1.30(17) . . . 4_655 ? C11 C12 C13 C14 -1.0(2) . . . . ? C1 C12 C13 C14 177.87(15) 4_655 . . . ? C12 C13 C14 C15 -1.2(3) . . . . ? C13 C14 C15 C16 1.6(3) . . . . ? C12 C11 C16 C15 -2.3(2) . . . . ? C1 C11 C16 C15 -179.58(14) . . . . ? C14 C15 C16 C11 0.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.155 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.033 data_wa1119 _database_code_depnum_ccdc_archive 'CCDC 873314' #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 B2 N3, Br' _chemical_formula_sum 'C20 H30 B2 Br N3' _chemical_formula_weight 414.00 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.1734(15) _cell_length_b 9.3798(7) _cell_length_c 24.6564(18) _cell_angle_alpha 90.00 _cell_angle_beta 95.039(6) _cell_angle_gamma 90.00 _cell_volume 4186.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9713 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 26.1 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 1.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5800 _exptl_absorpt_correction_T_max 0.6281 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _exptl_special_details ; ; _diffrn_ambient_temperature 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 13015 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 25.66 _reflns_number_total 3932 _reflns_number_gt 2968 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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. ; _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^)+(0.0484P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00137(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3932 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.001 _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 Br1 Br 0.616885(16) 0.23809(3) 0.449429(13) 0.04063(12) Uani 1 1 d . . . B2 B 0.63267(14) 0.7261(3) 0.38572(11) 0.0247(6) Uani 1 1 d . . . B1 B 0.67975(15) 0.5743(3) 0.36704(12) 0.0249(6) Uani 1 1 d . . . N1 N 0.62412(11) 0.4461(2) 0.34220(9) 0.0283(5) Uani 1 1 d . . . H1 H 0.6186(16) 0.393(3) 0.3721(13) 0.038(8) Uiso 1 1 d . . . N2 N 0.57880(10) 0.7424(2) 0.42225(8) 0.0255(4) Uani 1 1 d . . . N3 N 0.72783(11) 0.4966(2) 0.41844(9) 0.0277(5) Uani 1 1 d . . . H3 H 0.6975(18) 0.433(3) 0.4321(13) 0.047(9) Uiso 1 1 d . . . C1 C 0.73387(13) 0.6316(3) 0.32030(10) 0.0278(5) Uani 1 1 d . . . H1A H 0.7636 0.5529 0.3057 0.033 Uiso 1 1 calc R . . C2 C 0.66083(13) 0.8627(3) 0.35255(10) 0.0267(5) Uani 1 1 d . . . H2 H 0.6364 0.9539 0.3620 0.032 Uiso 1 1 calc R . . C3 C 0.54154(15) 0.8748(3) 0.43542(12) 0.0362(6) Uani 1 1 d . . . H3A H 0.5591 0.9530 0.4136 0.054 Uiso 1 1 calc R . . H3B H 0.5524 0.8964 0.4742 0.054 Uiso 1 1 calc R . . H3C H 0.4881 0.8636 0.4273 0.054 Uiso 1 1 calc R . . C4 C 0.55157(14) 0.6240(3) 0.45337(11) 0.0323(6) Uani 1 1 d . . . H4A H 0.5785 0.5369 0.4456 0.048 Uiso 1 1 calc R . . H4B H 0.4987 0.6102 0.4431 0.048 Uiso 1 1 calc R . . H4C H 0.5592 0.6454 0.4924 0.048 Uiso 1 1 calc R . . C5 C 0.55081(14) 0.4983(3) 0.31791(12) 0.0352(6) Uani 1 1 d . . . H5A H 0.5575 0.5530 0.2848 0.053 Uiso 1 1 calc R . . H5B H 0.5285 0.5594 0.3442 0.053 Uiso 1 1 calc R . . H5C H 0.5184 0.4167 0.3088 0.053 Uiso 1 1 calc R . . C6 C 0.65323(18) 0.3426(3) 0.30312(13) 0.0449(7) Uani 1 1 d . . . H6A H 0.6197 0.2609 0.2984 0.067 Uiso 1 1 calc R . . H6B H 0.7023 0.3098 0.3175 0.067 Uiso 1 1 calc R . . H6C H 0.6567 0.3895 0.2679 0.067 Uiso 1 1 calc R . . C7 C 0.79205(15) 0.4059(3) 0.40651(13) 0.0393(7) Uani 1 1 d . . . H7A H 0.8297 0.4653 0.3915 0.059 Uiso 1 1 calc R . . H7B H 0.7755 0.3322 0.3800 0.059 Uiso 1 1 calc R . . H7C H 0.8131 0.3606 0.4402 0.059 Uiso 1 1 calc R . . C8 C 0.75274(14) 0.5948(3) 0.46386(11) 0.0334(6) Uani 1 1 d . . . H8A H 0.7771 0.5398 0.4941 0.050 Uiso 1 1 calc R . . H8B H 0.7099 0.6449 0.4762 0.050 Uiso 1 1 calc R . . H8C H 0.7876 0.6644 0.4511 0.050 Uiso 1 1 calc R . . C11 C 0.74348(13) 0.8638(3) 0.36686(10) 0.0280(5) Uani 1 1 d . . . C12 C 0.78205(13) 0.7463(3) 0.34870(10) 0.0306(5) Uani 1 1 d . . . C13 C 0.85846(14) 0.7405(3) 0.36009(12) 0.0387(6) Uani 1 1 d . . . H13 H 0.8857 0.6646 0.3460 0.046 Uiso 1 1 calc R . . C14 C 0.89494(15) 0.8456(4) 0.39204(12) 0.0452(8) Uani 1 1 d . . . H14 H 0.9469 0.8399 0.4004 0.054 Uiso 1 1 calc R . . C15 C 0.85603(16) 0.9583(3) 0.41160(12) 0.0428(7) Uani 1 1 d . . . H15 H 0.8811 1.0280 0.4343 0.051 Uiso 1 1 calc R . . C16 C 0.78029(15) 0.9702(3) 0.39825(11) 0.0344(6) Uani 1 1 d . . . H16 H 0.7539 1.0498 0.4104 0.041 Uiso 1 1 calc R . . C21 C 0.64591(13) 0.8230(3) 0.29368(10) 0.0274(5) Uani 1 1 d . . . C22 C 0.68345(13) 0.7022(3) 0.27674(10) 0.0274(5) Uani 1 1 d . . . C23 C 0.67083(15) 0.6561(3) 0.22312(11) 0.0346(6) Uani 1 1 d . . . H23 H 0.6973 0.5767 0.2109 0.042 Uiso 1 1 calc R . . C24 C 0.61955(15) 0.7261(3) 0.18740(11) 0.0397(7) Uani 1 1 d . . . H24 H 0.6099 0.6922 0.1512 0.048 Uiso 1 1 calc R . . C25 C 0.58246(15) 0.8446(3) 0.20403(12) 0.0399(7) Uani 1 1 d . . . H25 H 0.5476 0.8921 0.1793 0.048 Uiso 1 1 calc R . . C26 C 0.59620(14) 0.8942(3) 0.25709(11) 0.0335(6) Uani 1 1 d . . . H26 H 0.5716 0.9770 0.2684 0.040 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 Br1 0.04590(17) 0.02902(16) 0.0480(2) 0.00677(14) 0.00971(12) -0.00416(13) B2 0.0238(12) 0.0291(14) 0.0213(14) -0.0024(11) 0.0029(10) -0.0064(11) B1 0.0254(13) 0.0284(14) 0.0213(15) -0.0011(11) 0.0048(11) -0.0052(11) N1 0.0329(11) 0.0279(11) 0.0244(12) -0.0026(9) 0.0043(9) -0.0046(9) N2 0.0259(9) 0.0264(10) 0.0251(11) -0.0020(9) 0.0066(8) -0.0035(8) N3 0.0282(11) 0.0314(11) 0.0241(12) -0.0010(9) 0.0063(9) -0.0021(9) C1 0.0273(12) 0.0341(13) 0.0233(14) -0.0025(11) 0.0095(10) -0.0007(10) C2 0.0291(12) 0.0296(12) 0.0224(13) -0.0022(10) 0.0079(10) -0.0052(10) C3 0.0406(15) 0.0326(14) 0.0374(17) -0.0058(12) 0.0154(12) 0.0000(11) C4 0.0303(13) 0.0363(14) 0.0318(15) 0.0028(12) 0.0106(11) -0.0049(11) C5 0.0314(14) 0.0432(16) 0.0302(15) -0.0033(12) -0.0026(11) -0.0097(11) C6 0.0553(18) 0.0370(15) 0.0429(19) -0.0197(14) 0.0075(15) -0.0029(13) C7 0.0360(14) 0.0428(16) 0.0398(17) 0.0014(14) 0.0077(12) 0.0109(12) C8 0.0328(13) 0.0403(15) 0.0272(15) -0.0021(12) 0.0029(11) -0.0038(11) C11 0.0317(13) 0.0337(13) 0.0193(13) 0.0027(10) 0.0065(10) -0.0094(10) C12 0.0296(11) 0.0415(15) 0.0217(12) 0.0041(12) 0.0084(9) -0.0093(11) C13 0.0288(12) 0.0551(17) 0.0332(15) 0.0067(14) 0.0088(11) -0.0043(13) C14 0.0262(13) 0.075(2) 0.0345(17) 0.0134(16) 0.0012(12) -0.0184(14) C15 0.0444(16) 0.0526(18) 0.0309(17) 0.0048(14) 0.0000(13) -0.0251(14) C16 0.0424(15) 0.0384(14) 0.0230(14) 0.0035(12) 0.0049(11) -0.0158(12) C21 0.0269(12) 0.0313(13) 0.0247(14) 0.0010(11) 0.0064(10) -0.0105(10) C22 0.0280(12) 0.0341(13) 0.0214(13) -0.0005(10) 0.0095(10) -0.0090(10) C23 0.0382(14) 0.0423(15) 0.0252(15) -0.0021(12) 0.0127(12) -0.0096(12) C24 0.0430(15) 0.0554(18) 0.0211(14) -0.0018(13) 0.0056(11) -0.0152(14) C25 0.0346(14) 0.0578(18) 0.0270(16) 0.0057(14) 0.0006(12) -0.0076(13) C26 0.0337(13) 0.0378(14) 0.0297(15) 0.0030(12) 0.0066(11) -0.0053(11) _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 B2 N2 1.396(3) . ? B2 C2 1.627(3) . ? B2 B1 1.744(4) . ? B1 N3 1.645(4) . ? B1 N1 1.653(3) . ? B1 C1 1.668(3) . ? N1 C5 1.494(3) . ? N1 C6 1.497(3) . ? N1 H1 0.90(3) . ? N2 C4 1.461(3) . ? N2 C3 1.464(3) . ? N3 C8 1.490(3) . ? N3 C7 1.494(3) . ? N3 H3 0.90(3) . ? C1 C22 1.503(4) . ? C1 C12 1.519(4) . ? C1 H1A 1.0000 . ? C2 C21 1.500(3) . ? C2 C11 1.513(3) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C11 C16 1.397(4) . ? C11 C12 1.400(4) . ? C12 C13 1.393(4) . ? C13 C14 1.394(4) . ? C13 H13 0.9500 . ? C14 C15 1.382(5) . ? C14 H14 0.9500 . ? C15 C16 1.391(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.390(4) . ? C21 C22 1.405(4) . ? C22 C23 1.391(4) . ? C23 C24 1.390(4) . ? C23 H23 0.9500 . ? C24 C25 1.380(4) . ? C24 H24 0.9500 . ? C25 C26 1.390(4) . ? C25 H25 0.9500 . ? C26 H26 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 N2 B2 C2 120.5(2) . . ? N2 B2 B1 130.4(2) . . ? C2 B2 B1 109.10(19) . . ? N3 B1 N1 103.26(18) . . ? N3 B1 C1 111.68(19) . . ? N1 B1 C1 110.9(2) . . ? N3 B1 B2 113.5(2) . . ? N1 B1 B2 113.17(19) . . ? C1 B1 B2 104.60(19) . . ? C5 N1 C6 107.9(2) . . ? C5 N1 B1 113.9(2) . . ? C6 N1 B1 118.1(2) . . ? C5 N1 H1 110.4(19) . . ? C6 N1 H1 103.7(19) . . ? B1 N1 H1 102.1(19) . . ? B2 N2 C4 123.0(2) . . ? B2 N2 C3 126.9(2) . . ? C4 N2 C3 110.11(19) . . ? C8 N3 C7 108.0(2) . . ? C8 N3 B1 114.3(2) . . ? C7 N3 B1 118.1(2) . . ? C8 N3 H3 107(2) . . ? C7 N3 H3 102(2) . . ? B1 N3 H3 106(2) . . ? C22 C1 C12 107.9(2) . . ? C22 C1 B1 106.03(19) . . ? C12 C1 B1 105.11(19) . . ? C22 C1 H1A 112.4 . . ? C12 C1 H1A 112.4 . . ? B1 C1 H1A 112.4 . . ? C21 C2 C11 108.59(19) . . ? C21 C2 B2 104.62(19) . . ? C11 C2 B2 103.7(2) . . ? C21 C2 H2 113.0 . . ? C11 C2 H2 113.0 . . ? B2 C2 H2 113.0 . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C16 C11 C12 120.7(2) . . ? C16 C11 C2 123.5(2) . . ? C12 C11 C2 115.8(2) . . ? C13 C12 C11 119.0(3) . . ? C13 C12 C1 126.1(3) . . ? C11 C12 C1 114.9(2) . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.3(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 119.3(3) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? C26 C21 C22 120.0(2) . . ? C26 C21 C2 124.1(2) . . ? C22 C21 C2 115.9(2) . . ? C23 C22 C21 119.3(3) . . ? C23 C22 C1 125.6(2) . . ? C21 C22 C1 115.1(2) . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 120.7(3) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 119.8(3) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C25 C26 C21 120.2(3) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? 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 N2 B2 B1 N3 -59.8(3) . . . . ? C2 B2 B1 N3 120.3(2) . . . . ? N2 B2 B1 N1 57.4(4) . . . . ? C2 B2 B1 N1 -122.5(2) . . . . ? N2 B2 B1 C1 178.3(2) . . . . ? C2 B2 B1 C1 -1.7(3) . . . . ? N3 B1 N1 C5 148.1(2) . . . . ? C1 B1 N1 C5 -92.2(2) . . . . ? B2 B1 N1 C5 25.0(3) . . . . ? N3 B1 N1 C6 -83.8(3) . . . . ? C1 B1 N1 C6 36.0(3) . . . . ? B2 B1 N1 C6 153.2(2) . . . . ? C2 B2 N2 C4 -179.7(2) . . . . ? B1 B2 N2 C4 0.3(4) . . . . ? C2 B2 N2 C3 0.3(4) . . . . ? B1 B2 N2 C3 -179.6(3) . . . . ? N1 B1 N3 C8 -150.14(19) . . . . ? C1 B1 N3 C8 90.6(2) . . . . ? B2 B1 N3 C8 -27.3(3) . . . . ? N1 B1 N3 C7 81.1(2) . . . . ? C1 B1 N3 C7 -38.1(3) . . . . ? B2 B1 N3 C7 -156.0(2) . . . . ? N3 B1 C1 C22 -178.87(19) . . . . ? N1 B1 C1 C22 66.5(2) . . . . ? B2 B1 C1 C22 -55.8(2) . . . . ? N3 B1 C1 C12 -64.7(2) . . . . ? N1 B1 C1 C12 -179.3(2) . . . . ? B2 B1 C1 C12 58.4(2) . . . . ? N2 B2 C2 C21 -122.4(2) . . . . ? B1 B2 C2 C21 57.6(2) . . . . ? N2 B2 C2 C11 123.9(2) . . . . ? B1 B2 C2 C11 -56.2(2) . . . . ? C21 C2 C11 C16 136.7(2) . . . . ? B2 C2 C11 C16 -112.5(3) . . . . ? C21 C2 C11 C12 -46.2(3) . . . . ? B2 C2 C11 C12 64.7(3) . . . . ? C16 C11 C12 C13 -3.2(4) . . . . ? C2 C11 C12 C13 179.6(2) . . . . ? C16 C11 C12 C1 173.7(2) . . . . ? C2 C11 C12 C1 -3.5(3) . . . . ? C22 C1 C12 C13 -132.0(3) . . . . ? B1 C1 C12 C13 115.2(3) . . . . ? C22 C1 C12 C11 51.4(3) . . . . ? B1 C1 C12 C11 -61.4(3) . . . . ? C11 C12 C13 C14 4.0(4) . . . . ? C1 C12 C13 C14 -172.4(2) . . . . ? C12 C13 C14 C15 -1.6(4) . . . . ? C13 C14 C15 C16 -1.9(4) . . . . ? C14 C15 C16 C11 2.8(4) . . . . ? C12 C11 C16 C15 -0.2(4) . . . . ? C2 C11 C16 C15 176.8(2) . . . . ? C11 C2 C21 C26 -134.0(2) . . . . ? B2 C2 C21 C26 115.8(3) . . . . ? C11 C2 C21 C22 48.7(3) . . . . ? B2 C2 C21 C22 -61.6(3) . . . . ? C26 C21 C22 C23 0.6(3) . . . . ? C2 C21 C22 C23 178.1(2) . . . . ? C26 C21 C22 C1 -178.2(2) . . . . ? C2 C21 C22 C1 -0.7(3) . . . . ? C12 C1 C22 C23 132.2(2) . . . . ? B1 C1 C22 C23 -115.6(3) . . . . ? C12 C1 C22 C21 -49.1(3) . . . . ? B1 C1 C22 C21 63.1(3) . . . . ? C21 C22 C23 C24 -2.3(4) . . . . ? C1 C22 C23 C24 176.3(2) . . . . ? C22 C23 C24 C25 2.2(4) . . . . ? C23 C24 C25 C26 -0.3(4) . . . . ? C24 C25 C26 C21 -1.4(4) . . . . ? C22 C21 C26 C25 1.3(4) . . . . ? C2 C21 C26 C25 -176.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Br1 0.90(3) 2.40(3) 3.298(2) 173(3) . N3 H3 Br1 0.90(3) 2.40(3) 3.286(2) 168(3) . _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.438 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.061 data_wa1181 _database_code_depnum_ccdc_archive 'CCDC 873315' #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 B2 Cl2 N2' _chemical_formula_sum 'C18 H24 B2 Cl2 N2' _chemical_formula_weight 360.91 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.8266(9) _cell_length_b 12.0793(8) _cell_length_c 9.9030(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1893.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7272 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8978 _exptl_absorpt_correction_T_max 0.9127 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _exptl_special_details ; ; _diffrn_ambient_temperature 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 7304 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 25.56 _reflns_number_total 3272 _reflns_number_gt 2943 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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. ; _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^)+(0.0301P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0104(10) _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 0.05(4) _refine_ls_number_reflns 3272 _refine_ls_number_parameters 230 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0578 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _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 0.17367(13) 0.61704(14) 0.4772(3) 0.0187(4) Uani 1 1 d . . . B2 B 0.14881(14) 0.56502(16) 0.6380(2) 0.0204(4) Uani 1 1 d . . . Cl1 Cl 0.22903(3) 0.75949(3) 0.47855(5) 0.02543(11) Uani 1 1 d . . . Cl2 Cl 0.03186(3) 0.52742(4) 0.66800(5) 0.02955(12) Uani 1 1 d . . . N1 N 0.09486(11) 0.63122(12) 0.37308(16) 0.0217(4) Uani 1 1 d . . . H1 H 0.0667(17) 0.5660(19) 0.375(2) 0.034(6) Uiso 1 1 d . . . N2 N 0.17159(12) 0.65034(13) 0.75967(16) 0.0243(4) Uani 1 1 d . . . H2 H 0.2210(17) 0.6744(17) 0.735(2) 0.026(6) Uiso 1 1 d . . . C1 C 0.24133(12) 0.52817(14) 0.41058(19) 0.0203(4) Uani 1 1 d . . . H1A H 0.2596 0.5508 0.3179 0.024 Uiso 1 1 calc R . . C2 C 0.20344(12) 0.44912(13) 0.6558(2) 0.0226(4) Uani 1 1 d . . . H2A H 0.1931 0.4129 0.7451 0.027 Uiso 1 1 calc R . . C3 C 0.11971(15) 0.65488(16) 0.2305(2) 0.0281(5) Uani 1 1 d . . . H3A H 0.0689 0.6689 0.1765 0.042 Uiso 1 1 calc R . . H3B H 0.1501 0.5911 0.1934 0.042 Uiso 1 1 calc R . . H3C H 0.1564 0.7202 0.2281 0.042 Uiso 1 1 calc R . . C4 C 0.02963(14) 0.71349(16) 0.4153(2) 0.0313(5) Uani 1 1 d . . . H4A H 0.0526 0.7885 0.4063 0.047 Uiso 1 1 calc R . . H4B H 0.0138 0.7001 0.5096 0.047 Uiso 1 1 calc R . . H4C H -0.0204 0.7059 0.3577 0.047 Uiso 1 1 calc R . . C5 C 0.17855(18) 0.60154(19) 0.8974(2) 0.0382(6) Uani 1 1 d . . . H5A H 0.1952 0.6592 0.9617 0.057 Uiso 1 1 calc R . . H5B H 0.2212 0.5428 0.8970 0.057 Uiso 1 1 calc R . . H5C H 0.1238 0.5705 0.9242 0.057 Uiso 1 1 calc R . . C6 C 0.11581(15) 0.75024(16) 0.7666(2) 0.0339(5) Uani 1 1 d . . . H6A H 0.0594 0.7283 0.7972 0.051 Uiso 1 1 calc R . . H6B H 0.1117 0.7841 0.6769 0.051 Uiso 1 1 calc R . . H6C H 0.1398 0.8038 0.8302 0.051 Uiso 1 1 calc R . . C11 C 0.19614(13) 0.41735(14) 0.4105(2) 0.0222(4) Uani 1 1 d . . . C12 C 0.17638(13) 0.37702(15) 0.5390(2) 0.0240(5) Uani 1 1 d . . . C13 C 0.13313(15) 0.27630(15) 0.5511(2) 0.0310(5) Uani 1 1 d . . . H13 H 0.1199 0.2475 0.6378 0.037 Uiso 1 1 calc R . . C14 C 0.10962(15) 0.21874(17) 0.4355(3) 0.0377(6) Uani 1 1 d . . . H14 H 0.0798 0.1508 0.4439 0.045 Uiso 1 1 calc R . . C15 C 0.12891(14) 0.25882(16) 0.3089(3) 0.0349(5) Uani 1 1 d . . . H15 H 0.1126 0.2184 0.2308 0.042 Uiso 1 1 calc R . . C16 C 0.17236(14) 0.35876(15) 0.2952(2) 0.0275(5) Uani 1 1 d . . . H16 H 0.1856 0.3867 0.2081 0.033 Uiso 1 1 calc R . . C21 C 0.31475(13) 0.51940(14) 0.50656(19) 0.0214(4) Uani 1 1 d . . . C22 C 0.29534(13) 0.47749(13) 0.63475(19) 0.0215(4) Uani 1 1 d . . . C23 C 0.35953(14) 0.46583(14) 0.7304(2) 0.0271(4) Uani 1 1 d . . . H23 H 0.3470 0.4380 0.8178 0.032 Uiso 1 1 calc R . . C24 C 0.44230(15) 0.49528(15) 0.6970(2) 0.0316(5) Uani 1 1 d . . . H24 H 0.4860 0.4864 0.7618 0.038 Uiso 1 1 calc R . . C25 C 0.46111(14) 0.53702(15) 0.5713(2) 0.0297(5) Uani 1 1 d . . . H25 H 0.5176 0.5566 0.5494 0.036 Uiso 1 1 calc R . . C26 C 0.39694(12) 0.55053(13) 0.4762(2) 0.0252(4) Uani 1 1 d . . . H26 H 0.4096 0.5812 0.3902 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 B1 0.0178(11) 0.0185(8) 0.0198(9) 0.0002(9) -0.0005(10) -0.0020(7) B2 0.0169(11) 0.0238(9) 0.0203(11) 0.0010(8) 0.0025(9) -0.0015(8) Cl1 0.0303(3) 0.02125(19) 0.0247(2) 0.0017(2) -0.0040(2) -0.00676(18) Cl2 0.0214(2) 0.0338(2) 0.0334(3) -0.0002(2) 0.0072(2) -0.0056(2) N1 0.0235(10) 0.0189(7) 0.0226(8) 0.0003(6) -0.0017(7) -0.0018(7) N2 0.0222(10) 0.0317(8) 0.0189(9) -0.0038(6) 0.0049(7) -0.0019(7) C1 0.0213(10) 0.0224(8) 0.0173(9) 0.0016(7) 0.0034(8) -0.0013(8) C2 0.0267(10) 0.0223(8) 0.0186(10) 0.0042(8) 0.0025(8) -0.0016(7) C3 0.0328(13) 0.0316(10) 0.0199(10) 0.0029(8) -0.0057(9) -0.0030(9) C4 0.0264(12) 0.0326(10) 0.0348(12) -0.0009(9) -0.0028(10) 0.0073(9) C5 0.0472(16) 0.0486(12) 0.0189(12) -0.0005(9) 0.0049(10) -0.0042(11) C6 0.0341(13) 0.0306(10) 0.0371(13) -0.0105(9) 0.0053(10) 0.0013(9) C11 0.0185(10) 0.0203(8) 0.0277(11) -0.0052(8) 0.0030(9) 0.0029(7) C12 0.0233(12) 0.0176(8) 0.0312(11) -0.0005(8) 0.0027(9) 0.0012(8) C13 0.0292(13) 0.0218(9) 0.0420(14) 0.0007(9) 0.0048(10) -0.0026(9) C14 0.0291(13) 0.0213(9) 0.0626(17) -0.0039(9) 0.0006(11) -0.0043(8) C15 0.0309(13) 0.0270(10) 0.0468(14) -0.0138(10) -0.0071(11) 0.0020(9) C16 0.0240(13) 0.0269(9) 0.0315(12) -0.0060(8) -0.0022(9) 0.0063(8) C21 0.0228(11) 0.0172(7) 0.0241(11) -0.0034(7) 0.0027(8) 0.0016(7) C22 0.0242(10) 0.0159(7) 0.0245(11) -0.0005(7) 0.0019(8) 0.0025(7) C23 0.0307(13) 0.0206(9) 0.0298(11) 0.0054(8) -0.0030(9) 0.0039(9) C24 0.0258(12) 0.0268(9) 0.0421(15) 0.0010(8) -0.0096(10) 0.0059(8) C25 0.0185(11) 0.0257(10) 0.0449(13) -0.0016(9) 0.0006(10) 0.0020(8) C26 0.0225(10) 0.0236(8) 0.0297(10) -0.0013(9) 0.0064(10) 0.0010(7) _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 N1 1.627(3) . ? B1 C1 1.653(3) . ? B1 B2 1.757(3) . ? B1 Cl1 1.9310(18) . ? B2 N2 1.626(3) . ? B2 C2 1.655(3) . ? B2 Cl2 1.929(2) . ? N1 C4 1.493(3) . ? N1 C3 1.493(3) . ? N1 H1 0.91(2) . ? N2 C5 1.490(3) . ? N2 C6 1.497(3) . ? N2 H2 0.87(3) . ? C1 C21 1.505(3) . ? C1 C11 1.518(3) . ? C1 H1A 1.0000 . ? C2 C22 1.509(3) . ? C2 C12 1.510(3) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C11 C16 1.394(3) . ? C11 C12 1.398(3) . ? C12 C13 1.401(3) . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C15 1.378(4) . ? C14 H14 0.9500 . ? C15 C16 1.396(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.387(3) . ? C21 C22 1.401(3) . ? C22 C23 1.396(3) . ? C23 C24 1.397(3) . ? C23 H23 0.9500 . ? C24 C25 1.375(3) . ? C24 H24 0.9500 . ? C25 C26 1.395(3) . ? C25 H25 0.9500 . ? C26 H26 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 N1 B1 C1 108.19(16) . . ? N1 B1 B2 116.12(15) . . ? C1 B1 B2 105.93(14) . . ? N1 B1 Cl1 104.98(11) . . ? C1 B1 Cl1 106.71(13) . . ? B2 B1 Cl1 114.45(14) . . ? N2 B2 C2 109.97(16) . . ? N2 B2 B1 113.30(14) . . ? C2 B2 B1 106.38(15) . . ? N2 B2 Cl2 104.35(13) . . ? C2 B2 Cl2 106.61(12) . . ? B1 B2 Cl2 116.03(14) . . ? C4 N1 C3 108.63(16) . . ? C4 N1 B1 115.01(15) . . ? C3 N1 B1 114.67(16) . . ? C4 N1 H1 103.4(16) . . ? C3 N1 H1 108.4(15) . . ? B1 N1 H1 105.9(15) . . ? C5 N2 C6 108.70(17) . . ? C5 N2 B2 116.37(16) . . ? C6 N2 B2 114.47(16) . . ? C5 N2 H2 108.9(16) . . ? C6 N2 H2 105.9(14) . . ? B2 N2 H2 101.6(15) . . ? C21 C1 C11 107.59(15) . . ? C21 C1 B1 107.09(15) . . ? C11 C1 B1 105.53(14) . . ? C21 C1 H1A 112.1 . . ? C11 C1 H1A 112.1 . . ? B1 C1 H1A 112.1 . . ? C22 C2 C12 107.39(16) . . ? C22 C2 B2 107.27(13) . . ? C12 C2 B2 104.96(16) . . ? C22 C2 H2A 112.3 . . ? C12 C2 H2A 112.3 . . ? B2 C2 H2A 112.3 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 H6A 109.5 . . ? N2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C16 C11 C12 120.51(16) . . ? C16 C11 C1 125.13(18) . . ? C12 C11 C1 114.33(16) . . ? C11 C12 C13 119.31(18) . . ? C11 C12 C2 115.65(15) . . ? C13 C12 C2 125.04(19) . . ? C14 C13 C12 119.7(2) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 C13 120.94(19) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 119.5(2) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C26 C21 C22 120.00(19) . . ? C26 C21 C1 124.62(18) . . ? C22 C21 C1 115.37(18) . . ? C23 C22 C21 119.44(19) . . ? C23 C22 C2 125.81(18) . . ? C21 C22 C2 114.75(17) . . ? C22 C23 C24 119.8(2) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 120.7(2) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C26 119.8(2) . . ? C24 C25 H25 120.1 . . ? C26 C25 H25 120.1 . . ? C21 C26 C25 120.3(2) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? 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 N1 B1 B2 N2 -118.91(16) . . . . ? C1 B1 B2 N2 121.00(17) . . . . ? Cl1 B1 B2 N2 3.7(2) . . . . ? N1 B1 B2 C2 120.16(16) . . . . ? C1 B1 B2 C2 0.07(19) . . . . ? Cl1 B1 B2 C2 -117.20(14) . . . . ? N1 B1 B2 Cl2 1.8(2) . . . . ? C1 B1 B2 Cl2 -118.30(14) . . . . ? Cl1 B1 B2 Cl2 124.43(12) . . . . ? C1 B1 N1 C4 -177.14(15) . . . . ? B2 B1 N1 C4 63.99(19) . . . . ? Cl1 B1 N1 C4 -63.49(19) . . . . ? C1 B1 N1 C3 -50.12(18) . . . . ? B2 B1 N1 C3 -168.99(15) . . . . ? Cl1 B1 N1 C3 63.53(17) . . . . ? C2 B2 N2 C5 -42.4(2) . . . . ? B1 B2 N2 C5 -161.24(18) . . . . ? Cl2 B2 N2 C5 71.7(2) . . . . ? C2 B2 N2 C6 -170.58(17) . . . . ? B1 B2 N2 C6 70.5(2) . . . . ? Cl2 B2 N2 C6 -56.58(18) . . . . ? N1 B1 C1 C21 178.22(14) . . . . ? B2 B1 C1 C21 -56.64(18) . . . . ? Cl1 B1 C1 C21 65.71(17) . . . . ? N1 B1 C1 C11 -67.35(18) . . . . ? B2 B1 C1 C11 57.79(19) . . . . ? Cl1 B1 C1 C11 -179.86(13) . . . . ? N2 B2 C2 C22 -66.58(19) . . . . ? B1 B2 C2 C22 56.47(19) . . . . ? Cl2 B2 C2 C22 -179.13(13) . . . . ? N2 B2 C2 C12 179.41(15) . . . . ? B1 B2 C2 C12 -57.54(19) . . . . ? Cl2 B2 C2 C12 66.86(16) . . . . ? C21 C1 C11 C16 -131.4(2) . . . . ? B1 C1 C11 C16 114.5(2) . . . . ? C21 C1 C11 C12 50.6(2) . . . . ? B1 C1 C11 C12 -63.5(2) . . . . ? C16 C11 C12 C13 0.7(3) . . . . ? C1 C11 C12 C13 178.79(18) . . . . ? C16 C11 C12 C2 -178.50(18) . . . . ? C1 C11 C12 C2 -0.4(3) . . . . ? C22 C2 C12 C11 -50.3(2) . . . . ? B2 C2 C12 C11 63.7(2) . . . . ? C22 C2 C12 C13 130.6(2) . . . . ? B2 C2 C12 C13 -115.5(2) . . . . ? C11 C12 C13 C14 -0.8(3) . . . . ? C2 C12 C13 C14 178.3(2) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? C13 C14 C15 C16 -0.3(3) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? C1 C11 C16 C15 -178.23(19) . . . . ? C14 C15 C16 C11 0.1(3) . . . . ? C11 C1 C21 C26 130.48(18) . . . . ? B1 C1 C21 C26 -116.49(18) . . . . ? C11 C1 C21 C22 -50.2(2) . . . . ? B1 C1 C21 C22 62.80(19) . . . . ? C26 C21 C22 C23 -1.0(3) . . . . ? C1 C21 C22 C23 179.67(15) . . . . ? C26 C21 C22 C2 178.71(15) . . . . ? C1 C21 C22 C2 -0.6(2) . . . . ? C12 C2 C22 C23 -129.58(19) . . . . ? B2 C2 C22 C23 118.05(19) . . . . ? C12 C2 C22 C21 50.73(19) . . . . ? B2 C2 C22 C21 -61.6(2) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? C2 C22 C23 C24 179.88(16) . . . . ? C22 C23 C24 C25 0.8(3) . . . . ? C23 C24 C25 C26 0.2(3) . . . . ? C22 C21 C26 C25 2.1(3) . . . . ? C1 C21 C26 C25 -178.67(16) . . . . ? C24 C25 C26 C21 -1.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl2 0.91(2) 2.81(3) 3.4378(17) 127.4(18) 2_564 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.215 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.032 data_wa1299 _database_code_depnum_ccdc_archive 'CCDC 873316' #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 B2 F6 N2 O4, 0.5(C H Cl3)' _chemical_formula_sum 'C22.50 H24.50 B2 Cl1.50 F6 N2 O4' _chemical_formula_weight 575.74 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' Cl Cl 0.1484 0.1585 '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' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.1883(6) _cell_length_b 15.1818(8) _cell_length_c 16.1826(8) _cell_angle_alpha 110.842(4) _cell_angle_beta 106.505(4) _cell_angle_gamma 98.129(4) _cell_volume 2583.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 23962 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1180 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9169 _exptl_absorpt_correction_T_max 0.9267 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _exptl_special_details ; ; _diffrn_ambient_temperature 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 30575 _diffrn_reflns_av_R_equivalents 0.0708 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.03 _reflns_number_total 9116 _reflns_number_gt 6917 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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. ; _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^)+(0.1007P)^2^+0.2249P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9116 _refine_ls_number_parameters 713 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1597 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _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 C1L C 0.9964(2) -0.0392(2) 0.7542(2) 0.0321(6) Uani 1 1 d . . . H1L H 1.0082 -0.0965 0.7691 0.039 Uiso 1 1 calc R . . Cl1 Cl 0.88881(9) -0.08370(9) 0.63993(7) 0.0662(3) Uani 1 1 d . . . Cl2 Cl 1.13232(8) 0.02224(7) 0.75947(8) 0.0585(3) Uani 1 1 d . . . Cl3 Cl 0.94774(8) 0.03624(6) 0.83841(6) 0.0476(2) Uani 1 1 d . . . B1 B 0.6212(2) 0.22124(18) 0.19281(18) 0.0168(5) Uani 1 1 d . . . B2 B 0.7261(2) 0.33630(18) 0.22971(18) 0.0175(5) Uani 1 1 d . . . N1 N 0.66601(19) 0.15381(14) 0.24604(14) 0.0194(4) Uani 1 1 d . . . H1 H 0.737(3) 0.149(2) 0.241(2) 0.025(7) Uiso 1 1 d . . . N2 N 0.6862(2) 0.43230(14) 0.27884(15) 0.0211(4) Uani 1 1 d . . . H2 H 0.619(3) 0.425(2) 0.243(2) 0.023(7) Uiso 1 1 d . . . O1 O 0.49749(15) 0.21459(12) 0.20221(12) 0.0208(4) Uani 1 1 d . . . O2 O 0.43963(16) 0.34863(13) 0.19694(14) 0.0306(4) Uani 1 1 d . . . O3 O 0.85192(15) 0.36361(12) 0.30436(11) 0.0217(4) Uani 1 1 d . . . O4 O 0.90802(17) 0.22369(13) 0.28382(13) 0.0298(4) Uani 1 1 d . . . C1 C 0.5928(2) 0.16224(16) 0.07730(16) 0.0176(5) Uani 1 1 d . . . H1B H 0.5365 0.0957 0.0498 0.021 Uiso 1 1 calc R . . C2 C 0.7433(2) 0.33570(17) 0.13135(16) 0.0192(5) Uani 1 1 d . . . H2B H 0.7988 0.3979 0.1436 0.023 Uiso 1 1 calc R . . C3 C 0.4251(2) 0.26723(18) 0.19528(17) 0.0225(5) Uani 1 1 d . . . C4 C 0.2996(2) 0.2119(2) 0.1798(2) 0.0312(6) Uani 1 1 d . . . F42 F 0.23328(17) 0.17394(19) 0.08807(15) 0.0650(7) Uani 1 1 d . . . F41 F 0.29790(17) 0.13899(14) 0.20618(19) 0.0575(6) Uani 1 1 d . . . F43 F 0.24699(16) 0.27078(13) 0.22703(15) 0.0451(5) Uani 1 1 d . . . C5 C 0.6847(3) 0.1976(2) 0.34894(18) 0.0312(6) Uani 1 1 d . . . H5A H 0.7341 0.2653 0.3784 0.047 Uiso 1 1 calc R . . H5B H 0.7246 0.1596 0.3795 0.047 Uiso 1 1 calc R . . H5C H 0.6077 0.1966 0.3566 0.047 Uiso 1 1 calc R . . C6 C 0.5914(2) 0.05054(18) 0.20177(19) 0.0285(6) Uani 1 1 d . . . H6A H 0.5792 0.0213 0.1341 0.043 Uiso 1 1 calc R . . H6B H 0.5143 0.0494 0.2093 0.043 Uiso 1 1 calc R . . H6C H 0.6316 0.0130 0.2328 0.043 Uiso 1 1 calc R . . C7 C 0.9244(2) 0.31205(18) 0.31736(17) 0.0230(5) Uani 1 1 d . A . C8 C 1.0480(2) 0.3755(2) 0.3878(2) 0.0321(6) Uani 1 1 d D . . F81 F 1.1248(7) 0.3221(5) 0.3958(6) 0.057(2) Uiso 0.293(3) 1 d PD A 1 F82 F 1.0386(8) 0.4124(7) 0.4753(5) 0.059(2) Uiso 0.293(3) 1 d PD A 1 F83 F 1.0887(7) 0.4442(6) 0.3692(6) 0.0534(19) Uiso 0.293(3) 1 d PD A 1 F81' F 1.1330(4) 0.3447(4) 0.3570(4) 0.0433(15) Uiso 0.407(7) 1 d PD A 2 F82' F 1.0659(4) 0.3704(4) 0.4708(3) 0.0337(13) Uiso 0.407(7) 1 d PD A 2 F83' F 1.0685(4) 0.4722(3) 0.4057(4) 0.0268(11) Uiso 0.407(7) 1 d PD A 2 F81" F 1.1225(6) 0.3806(6) 0.3399(5) 0.047(2) Uiso 0.300(7) 1 d PD A 3 F82" F 1.0984(7) 0.3401(6) 0.4480(6) 0.047(2) Uiso 0.300(7) 1 d PD A 3 F83" F 1.0543(7) 0.4701(5) 0.4379(6) 0.048(2) Uiso 0.300(7) 1 d PD A 3 C9 C 0.7601(3) 0.52684(18) 0.2913(2) 0.0301(6) Uani 1 1 d . . . H9A H 0.7676 0.5203 0.2308 0.045 Uiso 1 1 calc R . . H9B H 0.8392 0.5432 0.3390 0.045 Uiso 1 1 calc R . . H9C H 0.7219 0.5790 0.3122 0.045 Uiso 1 1 calc R . . C10 C 0.6750(3) 0.44317(19) 0.37090(18) 0.0293(6) Uani 1 1 d . . . H10A H 0.6264 0.3815 0.3632 0.044 Uiso 1 1 calc R . . H10B H 0.6371 0.4956 0.3916 0.044 Uiso 1 1 calc R . . H10C H 0.7542 0.4596 0.4186 0.044 Uiso 1 1 calc R . . C11 C 0.5415(2) 0.22702(17) 0.03404(16) 0.0191(5) Uani 1 1 d . . . C12 C 0.6206(2) 0.31872(17) 0.06293(16) 0.0197(5) Uani 1 1 d . . . C13 C 0.5809(2) 0.38557(18) 0.03017(18) 0.0262(5) Uani 1 1 d . . . H13 H 0.6338 0.4473 0.0489 0.031 Uiso 1 1 calc R . . C14 C 0.4634(3) 0.3624(2) -0.03017(19) 0.0325(6) Uani 1 1 d . . . H14 H 0.4368 0.4085 -0.0525 0.039 Uiso 1 1 calc R . . C15 C 0.3852(3) 0.2728(2) -0.05785(19) 0.0307(6) Uani 1 1 d . . . H15 H 0.3051 0.2575 -0.0985 0.037 Uiso 1 1 calc R . . C16 C 0.4253(2) 0.20469(18) -0.02546(17) 0.0245(5) Uani 1 1 d . . . H16 H 0.3722 0.1429 -0.0445 0.029 Uiso 1 1 calc R . . C21 C 0.7100(2) 0.15702(17) 0.06502(15) 0.0185(5) Uani 1 1 d . . . C22 C 0.7885(2) 0.24851(17) 0.09360(16) 0.0201(5) Uani 1 1 d . . . C23 C 0.9011(2) 0.25392(19) 0.08884(18) 0.0263(5) Uani 1 1 d . . . H23 H 0.9540 0.3157 0.1075 0.032 Uiso 1 1 calc R . . C24 C 0.9363(2) 0.1686(2) 0.05673(19) 0.0317(6) Uani 1 1 d . . . H24 H 1.0137 0.1722 0.0541 0.038 Uiso 1 1 calc R . . C25 C 0.8587(2) 0.0782(2) 0.02848(19) 0.0298(6) Uani 1 1 d . . . H25 H 0.8830 0.0200 0.0067 0.036 Uiso 1 1 calc R . . C26 C 0.7456(2) 0.07280(18) 0.03214(17) 0.0245(5) Uani 1 1 d . . . H26 H 0.6923 0.0108 0.0119 0.029 Uiso 1 1 calc R . . B1A B 0.6381(2) 0.22306(19) 0.69372(18) 0.0175(5) Uani 1 1 d . . . B2A B 0.7410(2) 0.33806(19) 0.73232(18) 0.0187(5) Uani 1 1 d . . . N1A N 0.6949(2) 0.15824(15) 0.74754(14) 0.0215(4) Uani 1 1 d . . . H1A H 0.767(3) 0.164(2) 0.744(2) 0.025(7) Uiso 1 1 d . . . N2A N 0.7039(2) 0.43394(15) 0.78702(15) 0.0232(4) Uani 1 1 d . . . H2A H 0.629(3) 0.424(2) 0.750(2) 0.029(8) Uiso 1 1 d . . . O1A O 0.51539(15) 0.21016(12) 0.70415(12) 0.0211(4) Uani 1 1 d . . . O2A O 0.45783(17) 0.34642(13) 0.70603(14) 0.0309(4) Uani 1 1 d . . . O3A O 0.85851(15) 0.33934(13) 0.80226(12) 0.0243(4) Uani 1 1 d . . . O4A O 1.00012(18) 0.45154(15) 0.79906(16) 0.0406(5) Uani 1 1 d . . . C1A C 0.6091(2) 0.16551(17) 0.57858(16) 0.0193(5) Uani 1 1 d . . . H1A1 H 0.5533 0.0987 0.5505 0.023 Uiso 1 1 calc R . . C2A C 0.7578(2) 0.34133(17) 0.63515(17) 0.0197(5) Uani 1 1 d . . . H2A1 H 0.8123 0.4046 0.6486 0.024 Uiso 1 1 calc R . . C3A C 0.4427(2) 0.26337(17) 0.70003(17) 0.0218(5) Uani 1 1 d . . . C4A C 0.3169(2) 0.20705(19) 0.68232(19) 0.0272(5) Uani 1 1 d . . . F41A F 0.31590(16) 0.13383(13) 0.70939(15) 0.0456(5) Uani 1 1 d . . . F42A F 0.25317(16) 0.16780(15) 0.58948(13) 0.0505(5) Uani 1 1 d . . . F43A F 0.26094(15) 0.26476(13) 0.72652(13) 0.0389(4) Uani 1 1 d . . . C5A C 0.6348(3) 0.05152(19) 0.6991(2) 0.0312(6) Uani 1 1 d . . . H5A1 H 0.6268 0.0271 0.6323 0.047 Uiso 1 1 calc R . . H5A2 H 0.5557 0.0401 0.7032 0.047 Uiso 1 1 calc R . . H5A3 H 0.6821 0.0171 0.7298 0.047 Uiso 1 1 calc R . . C6A C 0.7065(3) 0.1945(2) 0.84905(18) 0.0324(6) Uani 1 1 d . . . H6A1 H 0.7463 0.2649 0.8815 0.049 Uiso 1 1 calc R . . H6A2 H 0.7536 0.1597 0.8794 0.049 Uiso 1 1 calc R . . H6A3 H 0.6274 0.1829 0.8530 0.049 Uiso 1 1 calc R . . C7A C 0.9663(2) 0.38540(18) 0.81810(18) 0.0254(5) Uani 1 1 d . . . C8A C 1.0560(3) 0.3443(2) 0.8701(2) 0.0403(7) Uani 1 1 d . . . F81A F 1.0385(2) 0.24974(16) 0.8193(2) 0.0885(10) Uani 1 1 d . . . F82A F 1.16640(17) 0.38830(17) 0.88699(18) 0.0616(6) Uani 1 1 d . . . F83A F 1.0490(2) 0.3563(3) 0.95270(19) 0.0897(10) Uani 1 1 d . . . C9A C 0.7722(3) 0.53065(18) 0.8004(2) 0.0321(6) Uani 1 1 d . . . H9A1 H 0.7766 0.5267 0.7397 0.048 Uiso 1 1 calc R . . H9A2 H 0.8527 0.5482 0.8466 0.048 Uiso 1 1 calc R . . H9A3 H 0.7322 0.5806 0.8236 0.048 Uiso 1 1 calc R . . C10A C 0.6971(3) 0.4411(2) 0.8798(2) 0.0352(6) Uani 1 1 d . . . H10D H 0.6520 0.3778 0.8715 0.053 Uiso 1 1 calc R . . H10E H 0.6572 0.4913 0.9026 0.053 Uiso 1 1 calc R . . H10F H 0.7775 0.4588 0.9261 0.053 Uiso 1 1 calc R . . C11A C 0.5561(2) 0.23198(17) 0.53801(16) 0.0190(5) Uani 1 1 d . . . C12A C 0.6340(2) 0.32425(17) 0.56813(16) 0.0202(5) Uani 1 1 d . . . C13A C 0.5925(2) 0.39211(19) 0.53735(18) 0.0254(5) Uani 1 1 d . . . H13A H 0.6444 0.4548 0.5575 0.030 Uiso 1 1 calc R . . C14A C 0.4752(3) 0.3684(2) 0.47704(19) 0.0311(6) Uani 1 1 d . . . H14A H 0.4476 0.4148 0.4557 0.037 Uiso 1 1 calc R . . C15A C 0.3982(2) 0.2775(2) 0.44784(19) 0.0297(6) Uani 1 1 d . . . H15A H 0.3181 0.2617 0.4070 0.036 Uiso 1 1 calc R . . C16A C 0.4395(2) 0.20947(18) 0.47888(17) 0.0242(5) Uani 1 1 d . . . H16A H 0.3870 0.1472 0.4593 0.029 Uiso 1 1 calc R . . C21A C 0.7252(2) 0.16239(18) 0.56311(16) 0.0209(5) Uani 1 1 d . . . C22A C 0.8030(2) 0.25524(18) 0.59353(16) 0.0221(5) Uani 1 1 d . . . C23A C 0.9119(2) 0.2612(2) 0.58155(18) 0.0288(6) Uani 1 1 d . . . H23A H 0.9647 0.3234 0.6020 0.035 Uiso 1 1 calc R . . C24A C 0.9439(3) 0.1767(2) 0.5399(2) 0.0371(7) Uani 1 1 d . . . H24A H 1.0183 0.1813 0.5317 0.044 Uiso 1 1 calc R . . C25A C 0.8675(3) 0.0855(2) 0.5102(2) 0.0371(7) Uani 1 1 d . . . H25A H 0.8899 0.0278 0.4821 0.044 Uiso 1 1 calc R . . C26A C 0.7578(3) 0.0784(2) 0.52154(19) 0.0289(6) Uani 1 1 d . . . H26A H 0.7053 0.0158 0.5007 0.035 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 C1L 0.0251(14) 0.0364(14) 0.0383(15) 0.0166(12) 0.0148(12) 0.0091(11) Cl1 0.0452(5) 0.0947(8) 0.0425(5) 0.0172(5) 0.0070(4) 0.0195(5) Cl2 0.0348(4) 0.0577(5) 0.0879(7) 0.0290(5) 0.0341(5) 0.0056(4) Cl3 0.0516(5) 0.0526(5) 0.0490(4) 0.0191(4) 0.0302(4) 0.0258(4) B1 0.0145(12) 0.0190(12) 0.0204(12) 0.0090(10) 0.0087(10) 0.0076(10) B2 0.0157(13) 0.0180(12) 0.0177(12) 0.0067(10) 0.0060(10) 0.0036(10) N1 0.0190(11) 0.0217(10) 0.0220(10) 0.0122(8) 0.0092(8) 0.0067(8) N2 0.0179(11) 0.0200(10) 0.0224(10) 0.0067(8) 0.0065(9) 0.0040(8) O1 0.0165(8) 0.0236(8) 0.0253(8) 0.0109(7) 0.0100(7) 0.0073(7) O2 0.0210(9) 0.0261(9) 0.0458(11) 0.0155(8) 0.0113(8) 0.0102(7) O3 0.0176(9) 0.0235(8) 0.0210(8) 0.0071(7) 0.0051(7) 0.0059(7) O4 0.0236(9) 0.0290(10) 0.0354(10) 0.0125(8) 0.0082(8) 0.0102(8) C1 0.0167(11) 0.0164(10) 0.0187(11) 0.0072(9) 0.0062(9) 0.0028(9) C2 0.0185(12) 0.0196(11) 0.0204(11) 0.0092(9) 0.0082(10) 0.0031(9) C3 0.0176(12) 0.0251(12) 0.0228(12) 0.0075(10) 0.0076(10) 0.0060(10) C4 0.0211(13) 0.0307(14) 0.0400(15) 0.0104(12) 0.0134(12) 0.0082(11) F42 0.0225(9) 0.0950(17) 0.0445(11) 0.0087(11) 0.0029(9) -0.0071(10) F41 0.0350(10) 0.0435(10) 0.1133(18) 0.0449(12) 0.0378(11) 0.0117(8) F43 0.0360(10) 0.0456(10) 0.0688(12) 0.0242(9) 0.0361(9) 0.0188(8) C5 0.0396(16) 0.0386(15) 0.0232(13) 0.0189(11) 0.0132(12) 0.0134(12) C6 0.0305(14) 0.0245(12) 0.0361(14) 0.0190(11) 0.0120(12) 0.0069(11) C7 0.0223(13) 0.0281(13) 0.0208(11) 0.0106(10) 0.0097(10) 0.0086(10) C8 0.0198(13) 0.0373(15) 0.0345(14) 0.0120(12) 0.0055(11) 0.0105(11) C9 0.0322(15) 0.0165(11) 0.0394(15) 0.0088(11) 0.0149(12) 0.0035(10) C10 0.0315(14) 0.0286(13) 0.0246(12) 0.0044(10) 0.0141(11) 0.0081(11) C11 0.0216(12) 0.0222(11) 0.0170(11) 0.0099(9) 0.0088(10) 0.0080(9) C12 0.0220(12) 0.0236(12) 0.0174(11) 0.0102(9) 0.0099(10) 0.0074(10) C13 0.0317(14) 0.0240(12) 0.0274(13) 0.0141(10) 0.0119(11) 0.0091(11) C14 0.0399(16) 0.0330(14) 0.0313(14) 0.0191(12) 0.0105(12) 0.0191(12) C15 0.0276(14) 0.0384(14) 0.0253(13) 0.0147(11) 0.0035(11) 0.0153(12) C16 0.0225(13) 0.0252(12) 0.0220(12) 0.0081(10) 0.0051(10) 0.0055(10) C21 0.0179(12) 0.0240(11) 0.0152(10) 0.0097(9) 0.0063(9) 0.0061(9) C22 0.0188(12) 0.0267(12) 0.0154(11) 0.0096(9) 0.0059(9) 0.0065(10) C23 0.0194(12) 0.0338(14) 0.0239(12) 0.0102(10) 0.0092(10) 0.0041(10) C24 0.0230(13) 0.0458(16) 0.0281(13) 0.0132(12) 0.0126(11) 0.0138(12) C25 0.0300(14) 0.0335(14) 0.0283(13) 0.0102(11) 0.0130(12) 0.0175(11) C26 0.0290(13) 0.0242(12) 0.0226(12) 0.0100(10) 0.0105(10) 0.0108(10) B1A 0.0155(12) 0.0207(12) 0.0207(12) 0.0123(10) 0.0074(10) 0.0063(10) B2A 0.0175(13) 0.0190(12) 0.0182(12) 0.0071(10) 0.0063(10) 0.0034(10) N1A 0.0208(11) 0.0255(11) 0.0240(10) 0.0155(9) 0.0090(9) 0.0073(9) N2A 0.0217(11) 0.0210(10) 0.0256(11) 0.0080(8) 0.0097(9) 0.0040(9) O1A 0.0184(9) 0.0235(8) 0.0253(8) 0.0117(7) 0.0113(7) 0.0058(7) O2A 0.0246(10) 0.0263(10) 0.0482(11) 0.0176(8) 0.0178(9) 0.0108(8) O3A 0.0185(9) 0.0292(9) 0.0223(8) 0.0108(7) 0.0054(7) 0.0020(7) O4A 0.0242(10) 0.0381(11) 0.0597(14) 0.0266(10) 0.0106(10) 0.0020(9) C1A 0.0193(12) 0.0187(11) 0.0198(11) 0.0085(9) 0.0068(9) 0.0043(9) C2A 0.0172(12) 0.0222(11) 0.0226(11) 0.0119(9) 0.0087(10) 0.0041(9) C3A 0.0195(12) 0.0250(12) 0.0228(12) 0.0101(10) 0.0100(10) 0.0061(10) C4A 0.0206(13) 0.0299(13) 0.0340(14) 0.0132(11) 0.0131(11) 0.0086(10) F41A 0.0334(10) 0.0394(9) 0.0813(13) 0.0366(10) 0.0310(10) 0.0090(8) F42A 0.0272(9) 0.0701(13) 0.0336(9) 0.0107(9) 0.0040(8) -0.0036(9) F43A 0.0288(9) 0.0434(9) 0.0570(11) 0.0226(8) 0.0278(8) 0.0164(7) C5A 0.0382(16) 0.0240(13) 0.0364(14) 0.0180(11) 0.0132(12) 0.0089(11) C6A 0.0430(17) 0.0355(14) 0.0250(13) 0.0191(11) 0.0125(12) 0.0116(12) C7A 0.0199(12) 0.0255(12) 0.0244(12) 0.0060(10) 0.0064(10) 0.0023(10) C8A 0.0235(15) 0.0437(17) 0.0453(17) 0.0209(14) 0.0011(13) 0.0021(13) F81A 0.0618(16) 0.0417(12) 0.132(2) 0.0318(14) -0.0055(16) 0.0210(11) F82A 0.0224(9) 0.0726(14) 0.0878(16) 0.0427(12) 0.0065(10) 0.0103(9) F83A 0.0541(14) 0.169(3) 0.0654(15) 0.0825(19) 0.0093(12) 0.0226(17) C9A 0.0329(15) 0.0189(12) 0.0455(16) 0.0115(11) 0.0184(13) 0.0063(11) C10A 0.0473(18) 0.0314(14) 0.0282(14) 0.0072(11) 0.0222(13) 0.0103(13) C11A 0.0216(12) 0.0218(11) 0.0171(11) 0.0089(9) 0.0100(9) 0.0079(9) C12A 0.0208(12) 0.0247(12) 0.0201(11) 0.0120(9) 0.0104(10) 0.0071(10) C13A 0.0284(14) 0.0265(12) 0.0278(13) 0.0158(10) 0.0128(11) 0.0095(10) C14A 0.0350(15) 0.0342(14) 0.0336(14) 0.0213(12) 0.0123(12) 0.0182(12) C15A 0.0234(13) 0.0361(14) 0.0274(13) 0.0133(11) 0.0042(11) 0.0117(11) C16A 0.0217(13) 0.0271(12) 0.0221(12) 0.0086(10) 0.0079(10) 0.0059(10) C21A 0.0213(12) 0.0268(12) 0.0189(11) 0.0121(9) 0.0090(10) 0.0087(10) C22A 0.0214(12) 0.0306(13) 0.0185(11) 0.0128(10) 0.0089(10) 0.0092(10) C23A 0.0228(13) 0.0381(14) 0.0278(13) 0.0142(11) 0.0120(11) 0.0081(11) C24A 0.0266(15) 0.0545(18) 0.0405(16) 0.0223(14) 0.0193(13) 0.0198(13) C25A 0.0378(16) 0.0419(16) 0.0414(16) 0.0170(13) 0.0221(14) 0.0247(13) C26A 0.0340(15) 0.0304(13) 0.0286(13) 0.0140(11) 0.0153(12) 0.0147(11) _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 C1L Cl2 1.745(3) . ? C1L Cl3 1.750(3) . ? C1L Cl1 1.754(3) . ? C1L H1L 1.0000 . ? B1 O1 1.551(3) . ? B1 N1 1.615(3) . ? B1 C1 1.664(3) . ? B1 B2 1.799(3) . ? B2 O3 1.547(3) . ? B2 N2 1.609(3) . ? B2 C2 1.661(3) . ? N1 C5 1.490(3) . ? N1 C6 1.492(3) . ? N1 H1 0.90(3) . ? N2 C10 1.487(3) . ? N2 C9 1.496(3) . ? N2 H2 0.82(3) . ? O1 C3 1.279(3) . ? O2 C3 1.213(3) . ? O3 C7 1.283(3) . ? O4 C7 1.216(3) . ? C1 C11 1.505(3) . ? C1 C21 1.507(3) . ? C1 H1B 1.0000 . ? C2 C22 1.500(3) . ? C2 C12 1.509(3) . ? C2 H2B 1.0000 . ? C3 C4 1.542(3) . ? C4 F41 1.320(3) . ? C4 F43 1.322(3) . ? C4 F42 1.329(4) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.526(4) . ? C8 F83 1.259(7) . ? C8 F82" 1.320(7) . ? C8 F82' 1.331(5) . ? C8 F81 1.331(8) . ? C8 F81' 1.343(5) . ? C8 F83" 1.352(7) . ? C8 F81" 1.361(7) . ? C8 F83' 1.361(5) . ? C8 F82 1.371(8) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.380(4) . ? C11 C12 1.410(3) . ? C12 C13 1.386(4) . ? C13 C14 1.395(4) . ? C13 H13 0.9500 . ? C14 C15 1.385(4) . ? C14 H14 0.9500 . ? C15 C16 1.401(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.382(4) . ? C21 C22 1.405(3) . ? C22 C23 1.389(4) . ? C23 C24 1.392(4) . ? C23 H23 0.9500 . ? C24 C25 1.389(4) . ? C24 H24 0.9500 . ? C25 C26 1.389(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? B1A O1A 1.545(3) . ? B1A N1A 1.633(3) . ? B1A C1A 1.655(3) . ? B1A B2A 1.781(3) . ? B2A O3A 1.545(3) . ? B2A N2A 1.614(3) . ? B2A C2A 1.659(3) . ? N1A C5A 1.487(3) . ? N1A C6A 1.491(3) . ? N1A H1A 0.89(3) . ? N2A C9A 1.491(3) . ? N2A C10A 1.493(3) . ? N2A H2A 0.90(4) . ? O1A C3A 1.285(3) . ? O2A C3A 1.212(3) . ? O3A C7A 1.304(3) . ? O4A C7A 1.204(3) . ? C1A C21A 1.510(3) . ? C1A C11A 1.510(3) . ? C1A H1A1 1.0000 . ? C2A C22A 1.501(4) . ? C2A C12A 1.510(3) . ? C2A H2A1 1.0000 . ? C3A C4A 1.539(3) . ? C4A F43A 1.320(3) . ? C4A F41A 1.332(3) . ? C4A F42A 1.336(3) . ? C5A H5A1 0.9800 . ? C5A H5A2 0.9800 . ? C5A H5A3 0.9800 . ? C6A H6A1 0.9800 . ? C6A H6A2 0.9800 . ? C6A H6A3 0.9800 . ? C7A C8A 1.529(4) . ? C8A F83A 1.312(4) . ? C8A F82A 1.319(4) . ? C8A F81A 1.325(4) . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A H10D 0.9800 . ? C10A H10E 0.9800 . ? C10A H10F 0.9800 . ? C11A C16A 1.382(4) . ? C11A C12A 1.406(3) . ? C12A C13A 1.391(4) . ? C13A C14A 1.392(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.388(4) . ? C14A H14A 0.9500 . ? C15A C16A 1.394(4) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C21A C26A 1.386(4) . ? C21A C22A 1.411(3) . ? C22A C23A 1.390(4) . ? C23A C24A 1.389(4) . ? C23A H23A 0.9500 . ? C24A C25A 1.386(5) . ? C24A H24A 0.9500 . ? C25A C26A 1.395(4) . ? C25A H25A 0.9500 . ? C26A H26A 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 Cl2 C1L Cl3 111.18(16) . . ? Cl2 C1L Cl1 110.94(16) . . ? Cl3 C1L Cl1 110.66(17) . . ? Cl2 C1L H1L 108.0 . . ? Cl3 C1L H1L 108.0 . . ? Cl1 C1L H1L 108.0 . . ? O1 B1 N1 98.46(17) . . ? O1 B1 C1 105.11(18) . . ? N1 B1 C1 109.44(18) . . ? O1 B1 B2 122.42(19) . . ? N1 B1 B2 115.46(18) . . ? C1 B1 B2 105.22(17) . . ? O3 B2 N2 99.06(17) . . ? O3 B2 C2 107.10(18) . . ? N2 B2 C2 108.86(18) . . ? O3 B2 B1 120.56(18) . . ? N2 B2 B1 115.48(19) . . ? C2 B2 B1 105.25(17) . . ? C5 N1 C6 109.20(19) . . ? C5 N1 B1 113.22(19) . . ? C6 N1 B1 115.41(19) . . ? C5 N1 H1 107.4(19) . . ? C6 N1 H1 104.7(19) . . ? B1 N1 H1 106.2(18) . . ? C10 N2 C9 109.0(2) . . ? C10 N2 B2 113.34(19) . . ? C9 N2 B2 115.62(19) . . ? C10 N2 H2 106(2) . . ? C9 N2 H2 106(2) . . ? B2 N2 H2 107(2) . . ? C3 O1 B1 132.20(18) . . ? C7 O3 B2 131.43(19) . . ? C11 C1 C21 109.04(18) . . ? C11 C1 B1 104.88(18) . . ? C21 C1 B1 107.37(18) . . ? C11 C1 H1B 111.7 . . ? C21 C1 H1B 111.7 . . ? B1 C1 H1B 111.7 . . ? C22 C2 C12 108.82(19) . . ? C22 C2 B2 105.68(18) . . ? C12 C2 B2 106.16(18) . . ? C22 C2 H2B 111.9 . . ? C12 C2 H2B 111.9 . . ? B2 C2 H2B 111.9 . . ? O2 C3 O1 131.0(2) . . ? O2 C3 C4 118.2(2) . . ? O1 C3 C4 110.8(2) . . ? F41 C4 F43 106.6(2) . . ? F41 C4 F42 107.1(2) . . ? F43 C4 F42 108.2(2) . . ? F41 C4 C3 113.9(2) . . ? F43 C4 C3 111.6(2) . . ? F42 C4 C3 109.2(2) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? O4 C7 O3 130.0(2) . . ? O4 C7 C8 118.1(2) . . ? O3 C7 C8 112.0(2) . . ? F83 C8 F81 110.1(6) . . ? F82' C8 F81' 107.5(4) . . ? F82" C8 F83" 108.2(5) . . ? F82" C8 F81" 105.1(5) . . ? F83" C8 F81" 104.2(5) . . ? F82' C8 F83' 106.7(4) . . ? F81' C8 F83' 106.3(4) . . ? F83 C8 F82 110.2(6) . . ? F81 C8 F82 104.4(6) . . ? F83 C8 C7 113.6(4) . . ? F82" C8 C7 113.9(4) . . ? F82' C8 C7 110.1(3) . . ? F81 C8 C7 111.6(4) . . ? F81' C8 C7 111.1(3) . . ? F83" C8 C7 115.1(4) . . ? F81" C8 C7 109.5(3) . . ? F83' C8 C7 114.9(3) . . ? F82 C8 C7 106.6(4) . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 120.2(2) . . ? C16 C11 C1 125.1(2) . . ? C12 C11 C1 114.7(2) . . ? C13 C12 C11 119.4(2) . . ? C13 C12 C2 125.7(2) . . ? C11 C12 C2 114.9(2) . . ? C12 C13 C14 120.2(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.5(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C11 C16 C15 120.3(2) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C26 C21 C22 119.6(2) . . ? C26 C21 C1 126.0(2) . . ? C22 C21 C1 114.3(2) . . ? C23 C22 C21 120.0(2) . . ? C23 C22 C2 124.4(2) . . ? C21 C22 C2 115.6(2) . . ? C22 C23 C24 119.8(2) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C25 C24 C23 120.2(3) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C26 C25 C24 120.0(2) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C21 C26 C25 120.5(2) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? O1A B1A N1A 99.76(16) . . ? O1A B1A C1A 105.01(18) . . ? N1A B1A C1A 109.42(19) . . ? O1A B1A B2A 124.7(2) . . ? N1A B1A B2A 111.32(18) . . ? C1A B1A B2A 105.97(17) . . ? O3A B2A N2A 106.74(18) . . ? O3A B2A C2A 111.31(19) . . ? N2A B2A C2A 109.79(19) . . ? O3A B2A B1A 107.24(18) . . ? N2A B2A B1A 116.24(19) . . ? C2A B2A B1A 105.55(18) . . ? C5A N1A C6A 108.99(19) . . ? C5A N1A B1A 114.95(19) . . ? C6A N1A B1A 114.2(2) . . ? C5A N1A H1A 105.9(19) . . ? C6A N1A H1A 109.1(19) . . ? B1A N1A H1A 103.1(19) . . ? C9A N2A C10A 109.0(2) . . ? C9A N2A B2A 117.7(2) . . ? C10A N2A B2A 113.2(2) . . ? C9A N2A H2A 106.8(19) . . ? C10A N2A H2A 105(2) . . ? B2A N2A H2A 104(2) . . ? C3A O1A B1A 129.54(18) . . ? C7A O3A B2A 127.58(19) . . ? C21A C1A C11A 108.06(18) . . ? C21A C1A B1A 108.57(19) . . ? C11A C1A B1A 103.82(19) . . ? C21A C1A H1A1 112.0 . . ? C11A C1A H1A1 112.0 . . ? B1A C1A H1A1 112.0 . . ? C22A C2A C12A 108.1(2) . . ? C22A C2A B2A 106.48(18) . . ? C12A C2A B2A 105.38(18) . . ? C22A C2A H2A1 112.1 . . ? C12A C2A H2A1 112.1 . . ? B2A C2A H2A1 112.1 . . ? O2A C3A O1A 130.7(2) . . ? O2A C3A C4A 118.1(2) . . ? O1A C3A C4A 111.2(2) . . ? F43A C4A F41A 107.4(2) . . ? F43A C4A F42A 107.9(2) . . ? F41A C4A F42A 107.0(2) . . ? F43A C4A C3A 112.0(2) . . ? F41A C4A C3A 113.3(2) . . ? F42A C4A C3A 109.1(2) . . ? N1A C5A H5A1 109.5 . . ? N1A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 109.5 . . ? N1A C5A H5A3 109.5 . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? N1A C6A H6A1 109.5 . . ? N1A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? N1A C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? O4A C7A O3A 129.9(3) . . ? O4A C7A C8A 120.2(2) . . ? O3A C7A C8A 109.8(2) . . ? F83A C8A F82A 106.6(3) . . ? F83A C8A F81A 108.7(3) . . ? F82A C8A F81A 107.1(3) . . ? F83A C8A C7A 111.3(3) . . ? F82A C8A C7A 111.9(2) . . ? F81A C8A C7A 111.1(2) . . ? N2A C9A H9A1 109.5 . . ? N2A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? N2A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N2A C10A H10D 109.5 . . ? N2A C10A H10E 109.5 . . ? H10D C10A H10E 109.5 . . ? N2A C10A H10F 109.5 . . ? H10D C10A H10F 109.5 . . ? H10E C10A H10F 109.5 . . ? C16A C11A C12A 120.1(2) . . ? C16A C11A C1A 125.0(2) . . ? C12A C11A C1A 114.8(2) . . ? C13A C12A C11A 119.3(2) . . ? C13A C12A C2A 125.5(2) . . ? C11A C12A C2A 115.2(2) . . ? C12A C13A C14A 120.1(2) . . ? C12A C13A H13A 119.9 . . ? C14A C13A H13A 119.9 . . ? C15A C14A C13A 120.5(2) . . ? C15A C14A H14A 119.8 . . ? C13A C14A H14A 119.8 . . ? C14A C15A C16A 119.5(2) . . ? C14A C15A H15A 120.3 . . ? C16A C15A H15A 120.3 . . ? C11A C16A C15A 120.5(2) . . ? C11A C16A H16A 119.8 . . ? C15A C16A H16A 119.8 . . ? C26A C21A C22A 119.9(2) . . ? C26A C21A C1A 125.7(2) . . ? C22A C21A C1A 114.4(2) . . ? C23A C22A C21A 119.3(2) . . ? C23A C22A C2A 125.0(2) . . ? C21A C22A C2A 115.6(2) . . ? C24A C23A C22A 120.4(3) . . ? C24A C23A H23A 119.8 . . ? C22A C23A H23A 119.8 . . ? C25A C24A C23A 120.2(3) . . ? C25A C24A H24A 119.9 . . ? C23A C24A H24A 119.9 . . ? C24A C25A C26A 120.0(3) . . ? C24A C25A H25A 120.0 . . ? C26A C25A H25A 120.0 . . ? C21A C26A C25A 120.1(3) . . ? C21A C26A H26A 119.9 . . ? C25A C26A H26A 119.9 . . ? 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 B1 B2 O3 122.4(2) . . . . ? N1 B1 B2 O3 2.7(3) . . . . ? C1 B1 B2 O3 -118.1(2) . . . . ? O1 B1 B2 N2 3.4(3) . . . . ? N1 B1 B2 N2 -116.3(2) . . . . ? C1 B1 B2 N2 123.0(2) . . . . ? O1 B1 B2 C2 -116.6(2) . . . . ? N1 B1 B2 C2 123.7(2) . . . . ? C1 B1 B2 C2 2.9(2) . . . . ? O1 B1 N1 C5 -66.2(2) . . . . ? C1 B1 N1 C5 -175.6(2) . . . . ? B2 B1 N1 C5 66.0(3) . . . . ? O1 B1 N1 C6 60.7(2) . . . . ? C1 B1 N1 C6 -48.7(3) . . . . ? B2 B1 N1 C6 -167.1(2) . . . . ? O3 B2 N2 C10 -65.0(2) . . . . ? C2 B2 N2 C10 -176.66(19) . . . . ? B1 B2 N2 C10 65.3(3) . . . . ? O3 B2 N2 C9 61.9(2) . . . . ? C2 B2 N2 C9 -49.7(3) . . . . ? B1 B2 N2 C9 -167.8(2) . . . . ? N1 B1 O1 C3 161.5(2) . . . . ? C1 B1 O1 C3 -85.7(3) . . . . ? B2 B1 O1 C3 33.9(3) . . . . ? N2 B2 O3 C7 166.0(2) . . . . ? C2 B2 O3 C7 -80.9(3) . . . . ? B1 B2 O3 C7 39.1(3) . . . . ? O1 B1 C1 C11 70.0(2) . . . . ? N1 B1 C1 C11 174.93(18) . . . . ? B2 B1 C1 C11 -60.4(2) . . . . ? O1 B1 C1 C21 -174.05(17) . . . . ? N1 B1 C1 C21 -69.2(2) . . . . ? B2 B1 C1 C21 55.5(2) . . . . ? O3 B2 C2 C22 69.9(2) . . . . ? N2 B2 C2 C22 176.13(18) . . . . ? B1 B2 C2 C22 -59.5(2) . . . . ? O3 B2 C2 C12 -174.61(17) . . . . ? N2 B2 C2 C12 -68.4(2) . . . . ? B1 B2 C2 C12 56.0(2) . . . . ? B1 O1 C3 O2 -16.0(4) . . . . ? B1 O1 C3 C4 162.3(2) . . . . ? O2 C3 C4 F41 -161.1(2) . . . . ? O1 C3 C4 F41 20.4(3) . . . . ? O2 C3 C4 F43 -40.3(3) . . . . ? O1 C3 C4 F43 141.2(2) . . . . ? O2 C3 C4 F42 79.3(3) . . . . ? O1 C3 C4 F42 -99.2(3) . . . . ? B2 O3 C7 O4 -12.8(4) . . . . ? B2 O3 C7 C8 168.5(2) . . . . ? O4 C7 C8 F83 130.6(6) . . . . ? O3 C7 C8 F83 -50.5(6) . . . . ? O4 C7 C8 F82" -40.3(6) . . . . ? O3 C7 C8 F82" 138.6(5) . . . . ? O4 C7 C8 F82' -74.1(4) . . . . ? O3 C7 C8 F82' 104.8(4) . . . . ? O4 C7 C8 F81 5.5(6) . . . . ? O3 C7 C8 F81 -175.6(5) . . . . ? O4 C7 C8 F81' 44.8(4) . . . . ? O3 C7 C8 F81' -136.3(4) . . . . ? O4 C7 C8 F83" -166.1(5) . . . . ? O3 C7 C8 F83" 12.8(6) . . . . ? O4 C7 C8 F81" 77.0(5) . . . . ? O3 C7 C8 F81" -104.1(5) . . . . ? O4 C7 C8 F83' 165.5(4) . . . . ? O3 C7 C8 F83' -15.6(4) . . . . ? O4 C7 C8 F82 -107.9(5) . . . . ? O3 C7 C8 F82 71.1(5) . . . . ? C21 C1 C11 C16 133.3(2) . . . . ? B1 C1 C11 C16 -112.0(2) . . . . ? C21 C1 C11 C12 -50.1(3) . . . . ? B1 C1 C11 C12 64.6(2) . . . . ? C16 C11 C12 C13 -0.7(4) . . . . ? C1 C11 C12 C13 -177.5(2) . . . . ? C16 C11 C12 C2 177.4(2) . . . . ? C1 C11 C12 C2 0.6(3) . . . . ? C22 C2 C12 C13 -133.2(2) . . . . ? B2 C2 C12 C13 113.5(3) . . . . ? C22 C2 C12 C11 48.8(3) . . . . ? B2 C2 C12 C11 -64.5(2) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C2 C12 C13 C14 -177.3(2) . . . . ? C12 C13 C14 C15 0.1(4) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C12 C11 C16 C15 0.3(4) . . . . ? C1 C11 C16 C15 176.6(2) . . . . ? C14 C15 C16 C11 0.4(4) . . . . ? C11 C1 C21 C26 -132.4(2) . . . . ? B1 C1 C21 C26 114.5(2) . . . . ? C11 C1 C21 C22 49.8(3) . . . . ? B1 C1 C21 C22 -63.3(2) . . . . ? C26 C21 C22 C23 -0.1(3) . . . . ? C1 C21 C22 C23 177.9(2) . . . . ? C26 C21 C22 C2 -178.0(2) . . . . ? C1 C21 C22 C2 0.0(3) . . . . ? C12 C2 C22 C23 133.0(2) . . . . ? B2 C2 C22 C23 -113.4(2) . . . . ? C12 C2 C22 C21 -49.3(3) . . . . ? B2 C2 C22 C21 64.3(2) . . . . ? C21 C22 C23 C24 -0.7(4) . . . . ? C2 C22 C23 C24 176.9(2) . . . . ? C22 C23 C24 C25 0.7(4) . . . . ? C23 C24 C25 C26 0.1(4) . . . . ? C22 C21 C26 C25 0.9(3) . . . . ? C1 C21 C26 C25 -176.8(2) . . . . ? C24 C25 C26 C21 -0.9(4) . . . . ? O1A B1A B2A O3A 122.9(2) . . . . ? N1A B1A B2A O3A 3.5(2) . . . . ? C1A B1A B2A O3A -115.4(2) . . . . ? O1A B1A B2A N2A 3.6(3) . . . . ? N1A B1A B2A N2A -115.8(2) . . . . ? C1A B1A B2A N2A 125.3(2) . . . . ? O1A B1A B2A C2A -118.4(2) . . . . ? N1A B1A B2A C2A 122.2(2) . . . . ? C1A B1A B2A C2A 3.3(2) . . . . ? O1A B1A N1A C5A 66.3(2) . . . . ? C1A B1A N1A C5A -43.6(3) . . . . ? B2A B1A N1A C5A -160.4(2) . . . . ? O1A B1A N1A C6A -60.8(2) . . . . ? C1A B1A N1A C6A -170.6(2) . . . . ? B2A B1A N1A C6A 72.6(3) . . . . ? O3A B2A N2A C9A 74.4(3) . . . . ? C2A B2A N2A C9A -46.4(3) . . . . ? B1A B2A N2A C9A -166.1(2) . . . . ? O3A B2A N2A C10A -54.3(3) . . . . ? C2A B2A N2A C10A -175.1(2) . . . . ? B1A B2A N2A C10A 65.3(3) . . . . ? N1A B1A O1A C3A 158.6(2) . . . . ? C1A B1A O1A C3A -88.1(3) . . . . ? B2A B1A O1A C3A 34.0(3) . . . . ? N2A B2A O3A C7A -84.8(3) . . . . ? C2A B2A O3A C7A 35.0(3) . . . . ? B1A B2A O3A C7A 149.9(2) . . . . ? O1A B1A C1A C21A -172.29(17) . . . . ? N1A B1A C1A C21A -66.0(2) . . . . ? B2A B1A C1A C21A 54.1(2) . . . . ? O1A B1A C1A C11A 72.9(2) . . . . ? N1A B1A C1A C11A 179.22(18) . . . . ? B2A B1A C1A C11A -60.7(2) . . . . ? O3A B2A C2A C22A 56.9(2) . . . . ? N2A B2A C2A C22A 174.89(19) . . . . ? B1A B2A C2A C22A -59.1(2) . . . . ? O3A B2A C2A C12A 171.64(18) . . . . ? N2A B2A C2A C12A -70.4(2) . . . . ? B1A B2A C2A C12A 55.6(2) . . . . ? B1A O1A C3A O2A -16.8(4) . . . . ? B1A O1A C3A C4A 161.7(2) . . . . ? O2A C3A C4A F43A -36.1(3) . . . . ? O1A C3A C4A F43A 145.2(2) . . . . ? O2A C3A C4A F41A -157.7(2) . . . . ? O1A C3A C4A F41A 23.6(3) . . . . ? O2A C3A C4A F42A 83.3(3) . . . . ? O1A C3A C4A F42A -95.4(3) . . . . ? B2A O3A C7A O4A 17.0(4) . . . . ? B2A O3A C7A C8A -163.9(2) . . . . ? O4A C7A C8A F83A 117.9(3) . . . . ? O3A C7A C8A F83A -61.3(3) . . . . ? O4A C7A C8A F82A -1.3(4) . . . . ? O3A C7A C8A F82A 179.5(3) . . . . ? O4A C7A C8A F81A -120.9(3) . . . . ? O3A C7A C8A F81A 59.9(4) . . . . ? C21A C1A C11A C16A 132.1(2) . . . . ? B1A C1A C11A C16A -112.8(2) . . . . ? C21A C1A C11A C12A -50.6(3) . . . . ? B1A C1A C11A C12A 64.5(2) . . . . ? C16A C11A C12A C13A -0.4(3) . . . . ? C1A C11A C12A C13A -177.8(2) . . . . ? C16A C11A C12A C2A 178.0(2) . . . . ? C1A C11A C12A C2A 0.6(3) . . . . ? C22A C2A C12A C13A -132.4(2) . . . . ? B2A C2A C12A C13A 114.0(3) . . . . ? C22A C2A C12A C11A 49.3(3) . . . . ? B2A C2A C12A C11A -64.2(3) . . . . ? C11A C12A C13A C14A -0.3(4) . . . . ? C2A C12A C13A C14A -178.5(2) . . . . ? C12A C13A C14A C15A 0.7(4) . . . . ? C13A C14A C15A C16A -0.4(4) . . . . ? C12A C11A C16A C15A 0.6(4) . . . . ? C1A C11A C16A C15A 177.8(2) . . . . ? C14A C15A C16A C11A -0.2(4) . . . . ? C11A C1A C21A C26A -128.3(2) . . . . ? B1A C1A C21A C26A 119.7(3) . . . . ? C11A C1A C21A C22A 50.5(3) . . . . ? B1A C1A C21A C22A -61.4(2) . . . . ? C26A C21A C22A C23A -0.2(4) . . . . ? C1A C21A C22A C23A -179.1(2) . . . . ? C26A C21A C22A C2A 178.4(2) . . . . ? C1A C21A C22A C2A -0.5(3) . . . . ? C12A C2A C22A C23A 129.1(2) . . . . ? B2A C2A C22A C23A -118.0(3) . . . . ? C12A C2A C22A C21A -49.4(3) . . . . ? B2A C2A C22A C21A 63.5(3) . . . . ? C21A C22A C23A C24A 0.1(4) . . . . ? C2A C22A C23A C24A -178.3(2) . . . . ? C22A C23A C24A C25A -0.3(4) . . . . ? C23A C24A C25A C26A 0.4(4) . . . . ? C22A C21A C26A C25A 0.3(4) . . . . ? C1A C21A C26A C25A 179.1(2) . . . . ? C24A C25A C26A C21A -0.5(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.90(3) 2.02(3) 2.798(3) 144(3) . N2 H2 O2 0.82(3) 2.11(3) 2.804(3) 143(3) . N1A H1A O3A 0.89(3) 2.44(3) 2.835(3) 107(2) . N2A H2A O2A 0.90(4) 2.02(3) 2.807(3) 145(3) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.802 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.073 data_wa1325 _database_code_depnum_ccdc_archive 'CCDC 873317' #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H28 B2 N4 S2' _chemical_formula_sum 'C26 H28 B2 N4 S2' _chemical_formula_weight 482.26 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca21 _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 26.6672(6) _cell_length_b 8.5931(2) _cell_length_c 10.7151(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2455.41(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 28157 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.9 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.240 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9165 _exptl_absorpt_correction_T_max 0.9251 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _exptl_special_details ; ; _diffrn_ambient_temperature 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 29599 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.52 _reflns_number_total 5641 _reflns_number_gt 5431 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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. ; _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^)+(0.0730P)^2^+0.3817P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(6) _refine_ls_number_reflns 5641 _refine_ls_number_parameters 307 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.1090 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.001 _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 0.59802(7) 0.3481(3) 0.6373(2) 0.0286(4) Uani 1 1 d . . . B2 B 0.63578(7) 0.2290(2) 0.5465(2) 0.0288(4) Uani 1 1 d . . . C1 C 0.63430(7) 0.4268(2) 0.74508(18) 0.0296(4) Uani 1 1 d . . . H1 H 0.6162 0.5026 0.7997 0.035 Uiso 1 1 calc R . . C2 C 0.69208(7) 0.2259(2) 0.6115(2) 0.0315(4) Uani 1 1 d . . . H2 H 0.7161 0.1552 0.5679 0.038 Uiso 1 1 calc R . . C11 C 0.65354(7) 0.2862(2) 0.81541(19) 0.0319(4) Uani 1 1 d . . . C12 C 0.68381(7) 0.1831(2) 0.7465(2) 0.0326(4) Uani 1 1 d . . . C13 C 0.70146(8) 0.0485(3) 0.8037(2) 0.0398(5) Uani 1 1 d . . . H13 H 0.7227 -0.0205 0.7588 0.048 Uiso 1 1 calc R . . C14 C 0.68816(11) 0.0143(3) 0.9267(3) 0.0465(6) Uani 1 1 d . . . H14 H 0.7003 -0.0779 0.9650 0.056 Uiso 1 1 calc R . . C15 C 0.65744(9) 0.1135(3) 0.9929(2) 0.0449(5) Uani 1 1 d . . . H15 H 0.6481 0.0889 1.0762 0.054 Uiso 1 1 calc R . . C16 C 0.64021(8) 0.2499(3) 0.9375(2) 0.0371(4) Uani 1 1 d . . . H16 H 0.6192 0.3186 0.9833 0.044 Uiso 1 1 calc R . . C21 C 0.67711(7) 0.4996(2) 0.6730(2) 0.0310(4) Uani 1 1 d . . . C22 C 0.70664(7) 0.3955(2) 0.60316(19) 0.0316(4) Uani 1 1 d . . . C23 C 0.74262(7) 0.4534(3) 0.5210(2) 0.0365(4) Uani 1 1 d . . . H23 H 0.7622 0.3835 0.4726 0.044 Uiso 1 1 calc R . . C24 C 0.74998(8) 0.6135(3) 0.5095(2) 0.0416(5) Uani 1 1 d . . . H24 H 0.7743 0.6525 0.4529 0.050 Uiso 1 1 calc R . . C25 C 0.72168(9) 0.7154(3) 0.5809(2) 0.0416(5) Uani 1 1 d . . . H25 H 0.7271 0.8243 0.5741 0.050 Uiso 1 1 calc R . . C26 C 0.68519(8) 0.6587(3) 0.6626(2) 0.0366(4) Uani 1 1 d . . . H26 H 0.6659 0.7291 0.7111 0.044 Uiso 1 1 calc R . . S31 S 0.571041(17) 0.50390(5) 0.51664(5) 0.03196(12) Uani 1 1 d . . . N31 N 0.63703(6) 0.3044(2) 0.41522(15) 0.0292(3) Uani 1 1 d . . . C31 C 0.61207(7) 0.4391(2) 0.40317(18) 0.0299(4) Uani 1 1 d . . . N32 N 0.62618(7) 0.5090(2) 0.29594(19) 0.0369(4) Uani 1 1 d . . . C32 C 0.66170(8) 0.4142(3) 0.2391(2) 0.0418(5) Uani 1 1 d . . . H32 H 0.6782 0.4341 0.1622 0.050 Uiso 1 1 calc R . . C33 C 0.66839(8) 0.2894(3) 0.3126(2) 0.0367(4) Uani 1 1 d . . . H33 H 0.6907 0.2054 0.2970 0.044 Uiso 1 1 calc R . . C34 C 0.61201(9) 0.6670(3) 0.2568(2) 0.0438(5) Uani 1 1 d . . . H34 H 0.5830 0.7006 0.3095 0.053 Uiso 1 1 calc R . . C35 C 0.59498(13) 0.6686(4) 0.1219(3) 0.0634(8) Uani 1 1 d . . . H35A H 0.5674 0.5946 0.1110 0.095 Uiso 1 1 calc R . . H35B H 0.6230 0.6388 0.0678 0.095 Uiso 1 1 calc R . . H35C H 0.5835 0.7733 0.0996 0.095 Uiso 1 1 calc R . . C36 C 0.65469(11) 0.7792(3) 0.2802(3) 0.0556(6) Uani 1 1 d . . . H36A H 0.6643 0.7750 0.3685 0.083 Uiso 1 1 calc R . . H36B H 0.6440 0.8850 0.2591 0.083 Uiso 1 1 calc R . . H36C H 0.6835 0.7502 0.2284 0.083 Uiso 1 1 calc R . . S41 S 0.600827(18) 0.02421(5) 0.54683(5) 0.03184(12) Uani 1 1 d . . . N41 N 0.55635(6) 0.24074(19) 0.69097(16) 0.0292(3) Uani 1 1 d . . . C41 C 0.55814(6) 0.0910(2) 0.65565(18) 0.0290(4) Uani 1 1 d . . . N42 N 0.52446(7) 0.00853(19) 0.72279(18) 0.0342(4) Uani 1 1 d . . . C42 C 0.50110(8) 0.1106(3) 0.8048(2) 0.0382(5) Uani 1 1 d . . . H42 H 0.4758 0.0851 0.8638 0.046 Uiso 1 1 calc R . . C43 C 0.52102(7) 0.2528(3) 0.7849(2) 0.0350(4) Uani 1 1 d . . . H43 H 0.5123 0.3454 0.8281 0.042 Uiso 1 1 calc R . . C44 C 0.51724(9) -0.1609(3) 0.7160(2) 0.0417(5) Uani 1 1 d . . . H44 H 0.5395 -0.2027 0.6488 0.050 Uiso 1 1 calc R . . C45 C 0.46320(11) -0.1976(4) 0.6815(4) 0.0651(8) Uani 1 1 d . . . H45A H 0.4551 -0.1485 0.6015 0.098 Uiso 1 1 calc R . . H45B H 0.4408 -0.1573 0.7463 0.098 Uiso 1 1 calc R . . H45C H 0.4589 -0.3105 0.6745 0.098 Uiso 1 1 calc R . . C46 C 0.53295(14) -0.2334(3) 0.8389(3) 0.0652(8) Uani 1 1 d . . . H46A H 0.5680 -0.2071 0.8563 0.098 Uiso 1 1 calc R . . H46B H 0.5293 -0.3467 0.8339 0.098 Uiso 1 1 calc R . . H46C H 0.5116 -0.1933 0.9061 0.098 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 B1 0.0250(8) 0.0269(9) 0.0338(10) 0.0011(8) 0.0013(7) 0.0001(7) B2 0.0255(8) 0.0283(8) 0.0327(10) -0.0023(8) -0.0001(8) -0.0015(7) C1 0.0292(8) 0.0296(9) 0.0299(9) -0.0019(7) 0.0020(7) -0.0003(7) C2 0.0250(8) 0.0323(10) 0.0372(10) -0.0031(8) 0.0012(7) 0.0015(7) C11 0.0293(9) 0.0312(9) 0.0351(10) -0.0012(8) -0.0035(7) -0.0037(7) C12 0.0280(8) 0.0321(9) 0.0378(10) -0.0018(8) -0.0058(7) -0.0011(7) C13 0.0373(10) 0.0345(10) 0.0477(12) -0.0006(9) -0.0083(9) 0.0039(8) C14 0.0520(13) 0.0379(11) 0.0498(14) 0.0094(9) -0.0135(11) 0.0003(9) C15 0.0514(12) 0.0439(11) 0.0395(11) 0.0075(9) -0.0050(10) -0.0040(10) C16 0.0380(10) 0.0386(10) 0.0346(10) 0.0003(8) -0.0024(8) -0.0044(8) C21 0.0278(9) 0.0315(10) 0.0337(9) -0.0010(7) -0.0014(7) -0.0025(7) C22 0.0240(8) 0.0357(10) 0.0350(9) -0.0011(8) -0.0027(7) -0.0016(7) C23 0.0253(8) 0.0426(9) 0.0416(11) -0.0022(9) 0.0006(8) -0.0023(7) C24 0.0336(9) 0.0465(11) 0.0448(11) 0.0012(9) 0.0032(8) -0.0118(9) C25 0.0436(11) 0.0361(10) 0.0451(12) 0.0006(8) 0.0020(9) -0.0113(9) C26 0.0371(9) 0.0340(11) 0.0388(11) -0.0029(8) 0.0002(8) -0.0051(8) S31 0.0279(2) 0.0317(2) 0.0362(3) 0.00173(17) 0.00350(18) 0.00464(16) N31 0.0259(7) 0.0318(8) 0.0299(8) -0.0030(6) 0.0013(6) -0.0004(6) C31 0.0258(8) 0.0331(9) 0.0308(9) 0.0017(8) -0.0005(7) 0.0001(7) N32 0.0359(9) 0.0409(10) 0.0338(9) 0.0059(7) 0.0034(8) 0.0034(7) C32 0.0378(10) 0.0534(13) 0.0344(10) 0.0002(9) 0.0074(9) 0.0021(9) C33 0.0329(9) 0.0431(11) 0.0341(10) -0.0041(9) 0.0059(8) 0.0030(8) C34 0.0439(11) 0.0442(12) 0.0434(12) 0.0105(10) 0.0037(9) 0.0068(10) C35 0.081(2) 0.0609(17) 0.0478(14) 0.0162(13) -0.0118(14) 0.0034(15) C36 0.0607(16) 0.0455(13) 0.0606(16) 0.0046(12) 0.0007(13) -0.0009(12) S41 0.0308(2) 0.02792(19) 0.0368(2) -0.0041(2) 0.00325(19) -0.00115(16) N41 0.0235(7) 0.0294(8) 0.0346(8) 0.0001(6) 0.0029(6) -0.0002(6) C41 0.0239(7) 0.0290(9) 0.0340(9) 0.0008(7) -0.0014(7) -0.0010(7) N42 0.0301(8) 0.0305(8) 0.0421(10) 0.0008(7) 0.0044(7) -0.0036(6) C42 0.0315(9) 0.0385(11) 0.0445(11) 0.0013(8) 0.0126(8) -0.0012(8) C43 0.0298(9) 0.0352(10) 0.0398(10) 0.0001(8) 0.0085(8) 0.0022(8) C44 0.0419(11) 0.0307(10) 0.0526(13) -0.0007(9) 0.0068(10) -0.0089(8) C45 0.0577(16) 0.0566(16) 0.081(2) 0.0000(15) -0.0071(15) -0.0272(13) C46 0.077(2) 0.0444(14) 0.074(2) 0.0170(14) -0.0054(16) 0.0046(13) _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 N41 1.554(2) . ? B1 C1 1.651(3) . ? B1 B2 1.734(3) . ? B1 S31 1.995(2) . ? B2 N31 1.549(3) . ? B2 C2 1.656(3) . ? B2 S41 1.991(2) . ? C1 C11 1.513(3) . ? C1 C21 1.514(3) . ? C1 H1 1.0000 . ? C2 C12 1.509(3) . ? C2 C22 1.511(3) . ? C2 H2 1.0000 . ? C11 C16 1.391(3) . ? C11 C12 1.408(3) . ? C12 C13 1.391(3) . ? C13 C14 1.396(4) . ? C13 H13 0.9500 . ? C14 C15 1.379(4) . ? C14 H14 0.9500 . ? C15 C16 1.392(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.388(3) . ? C21 C22 1.407(3) . ? C22 C23 1.394(3) . ? C23 C24 1.395(3) . ? C23 H23 0.9500 . ? C24 C25 1.386(3) . ? C24 H24 0.9500 . ? C25 C26 1.397(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? S31 C31 1.728(2) . ? N31 C31 1.341(3) . ? N31 C33 1.388(2) . ? C31 N32 1.350(3) . ? N32 C32 1.390(3) . ? N32 C34 1.471(3) . ? C32 C33 1.343(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C36 1.512(4) . ? C34 C35 1.515(4) . ? C34 H34 1.0000 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? S41 C41 1.7277(19) . ? N41 C41 1.342(2) . ? N41 C43 1.382(3) . ? C41 N42 1.352(2) . ? N42 C42 1.389(3) . ? N42 C44 1.471(3) . ? C42 C43 1.349(3) . ? C42 H42 0.9500 . ? C43 H43 0.9500 . ? C44 C46 1.516(4) . ? C44 C45 1.521(4) . ? C44 H44 1.0000 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? 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 N41 B1 C1 113.77(16) . . ? N41 B1 B2 105.81(15) . . ? C1 B1 B2 107.09(14) . . ? N41 B1 S31 112.34(13) . . ? C1 B1 S31 112.93(13) . . ? B2 B1 S31 103.99(13) . . ? N31 B2 C2 111.68(15) . . ? N31 B2 B1 105.97(14) . . ? C2 B2 B1 107.44(15) . . ? N31 B2 S41 112.42(13) . . ? C2 B2 S41 114.19(13) . . ? B1 B2 S41 104.40(12) . . ? C11 C1 C21 109.16(16) . . ? C11 C1 B1 102.72(15) . . ? C21 C1 B1 104.75(16) . . ? C11 C1 H1 113.1 . . ? C21 C1 H1 113.1 . . ? B1 C1 H1 113.1 . . ? C12 C2 C22 109.27(16) . . ? C12 C2 B2 105.95(15) . . ? C22 C2 B2 101.11(15) . . ? C12 C2 H2 113.2 . . ? C22 C2 H2 113.2 . . ? B2 C2 H2 113.2 . . ? C16 C11 C12 119.9(2) . . ? C16 C11 C1 124.12(19) . . ? C12 C11 C1 115.83(18) . . ? C13 C12 C11 119.1(2) . . ? C13 C12 C2 125.1(2) . . ? C11 C12 C2 115.66(18) . . ? C12 C13 C14 120.3(2) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.8(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 120.4(2) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C26 C21 C22 119.7(2) . . ? C26 C21 C1 124.44(19) . . ? C22 C21 C1 115.49(17) . . ? C23 C22 C21 119.62(19) . . ? C23 C22 C2 123.96(18) . . ? C21 C22 C2 115.96(17) . . ? C22 C23 C24 120.29(19) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 119.9(2) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 120.3(2) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C21 C26 C25 120.2(2) . . ? C21 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C31 S31 B1 90.65(9) . . ? C31 N31 C33 107.63(17) . . ? C31 N31 B2 115.96(15) . . ? C33 N31 B2 133.93(17) . . ? N31 C31 N32 109.12(17) . . ? N31 C31 S31 121.63(15) . . ? N32 C31 S31 129.21(16) . . ? C31 N32 C32 107.62(18) . . ? C31 N32 C34 125.58(19) . . ? C32 N32 C34 126.23(19) . . ? C33 C32 N32 107.53(19) . . ? C33 C32 H32 126.2 . . ? N32 C32 H32 126.2 . . ? C32 C33 N31 108.10(19) . . ? C32 C33 H33 125.9 . . ? N31 C33 H33 125.9 . . ? N32 C34 C36 110.3(2) . . ? N32 C34 C35 110.9(2) . . ? C36 C34 C35 112.2(2) . . ? N32 C34 H34 107.7 . . ? C36 C34 H34 107.7 . . ? C35 C34 H34 107.7 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C41 S41 B2 90.91(9) . . ? C41 N41 C43 107.53(16) . . ? C41 N41 B1 116.05(15) . . ? C43 N41 B1 135.41(17) . . ? N41 C41 N42 109.21(16) . . ? N41 C41 S41 122.17(14) . . ? N42 C41 S41 128.52(15) . . ? C41 N42 C42 107.66(16) . . ? C41 N42 C44 125.44(18) . . ? C42 N42 C44 126.73(19) . . ? C43 C42 N42 107.18(18) . . ? C43 C42 H42 126.4 . . ? N42 C42 H42 126.4 . . ? C42 C43 N41 108.41(18) . . ? C42 C43 H43 125.8 . . ? N41 C43 H43 125.8 . . ? N42 C44 C46 109.1(2) . . ? N42 C44 C45 109.9(2) . . ? C46 C44 C45 112.8(2) . . ? N42 C44 H44 108.3 . . ? C46 C44 H44 108.3 . . ? C45 C44 H44 108.3 . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C44 C46 H46A 109.5 . . ? C44 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C44 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? 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 N41 B1 B2 N31 124.55(15) . . . . ? C1 B1 B2 N31 -113.77(16) . . . . ? S31 B1 B2 N31 6.01(16) . . . . ? N41 B1 B2 C2 -115.94(16) . . . . ? C1 B1 B2 C2 5.75(19) . . . . ? S31 B1 B2 C2 125.53(14) . . . . ? N41 B1 B2 S41 5.66(17) . . . . ? C1 B1 B2 S41 127.35(14) . . . . ? S31 B1 B2 S41 -112.87(11) . . . . ? N41 B1 C1 C11 55.61(19) . . . . ? B2 B1 C1 C11 -60.93(18) . . . . ? S31 B1 C1 C11 -174.79(13) . . . . ? N41 B1 C1 C21 169.66(15) . . . . ? B2 B1 C1 C21 53.12(18) . . . . ? S31 B1 C1 C21 -60.75(17) . . . . ? N31 B2 C2 C12 168.08(15) . . . . ? B1 B2 C2 C12 52.28(19) . . . . ? S41 B2 C2 C12 -62.98(18) . . . . ? N31 B2 C2 C22 54.14(19) . . . . ? B1 B2 C2 C22 -61.66(18) . . . . ? S41 B2 C2 C22 -176.93(13) . . . . ? C21 C1 C11 C16 138.0(2) . . . . ? B1 C1 C11 C16 -111.2(2) . . . . ? C21 C1 C11 C12 -46.8(2) . . . . ? B1 C1 C11 C12 64.0(2) . . . . ? C16 C11 C12 C13 -2.3(3) . . . . ? C1 C11 C12 C13 -177.81(18) . . . . ? C16 C11 C12 C2 174.49(17) . . . . ? C1 C11 C12 C2 -1.0(2) . . . . ? C22 C2 C12 C13 -135.6(2) . . . . ? B2 C2 C12 C13 116.2(2) . . . . ? C22 C2 C12 C11 47.8(2) . . . . ? B2 C2 C12 C11 -60.4(2) . . . . ? C11 C12 C13 C14 1.7(3) . . . . ? C2 C12 C13 C14 -174.8(2) . . . . ? C12 C13 C14 C15 -0.1(4) . . . . ? C13 C14 C15 C16 -1.0(4) . . . . ? C12 C11 C16 C15 1.3(3) . . . . ? C1 C11 C16 C15 176.37(19) . . . . ? C14 C15 C16 C11 0.4(3) . . . . ? C11 C1 C21 C26 -139.0(2) . . . . ? B1 C1 C21 C26 111.6(2) . . . . ? C11 C1 C21 C22 47.8(2) . . . . ? B1 C1 C21 C22 -61.7(2) . . . . ? C26 C21 C22 C23 -2.1(3) . . . . ? C1 C21 C22 C23 171.51(18) . . . . ? C26 C21 C22 C2 -174.63(19) . . . . ? C1 C21 C22 C2 -1.0(3) . . . . ? C12 C2 C22 C23 141.05(19) . . . . ? B2 C2 C22 C23 -107.5(2) . . . . ? C12 C2 C22 C21 -46.8(2) . . . . ? B2 C2 C22 C21 64.7(2) . . . . ? C21 C22 C23 C24 1.1(3) . . . . ? C2 C22 C23 C24 173.00(19) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C23 C24 C25 C26 -1.1(3) . . . . ? C22 C21 C26 C25 1.5(3) . . . . ? C1 C21 C26 C25 -171.5(2) . . . . ? C24 C25 C26 C21 0.1(3) . . . . ? N41 B1 S31 C31 -124.02(15) . . . . ? C1 B1 S31 C31 105.66(14) . . . . ? B2 B1 S31 C31 -10.07(13) . . . . ? C2 B2 N31 C31 -114.19(18) . . . . ? B1 B2 N31 C31 2.5(2) . . . . ? S41 B2 N31 C31 115.94(15) . . . . ? C2 B2 N31 C33 45.3(3) . . . . ? B1 B2 N31 C33 162.0(2) . . . . ? S41 B2 N31 C33 -84.6(2) . . . . ? C33 N31 C31 N32 0.6(2) . . . . ? B2 N31 C31 N32 165.27(16) . . . . ? C33 N31 C31 S31 -177.17(15) . . . . ? B2 N31 C31 S31 -12.5(2) . . . . ? B1 S31 C31 N31 13.96(17) . . . . ? B1 S31 C31 N32 -163.3(2) . . . . ? N31 C31 N32 C32 -0.4(2) . . . . ? S31 C31 N32 C32 177.17(16) . . . . ? N31 C31 N32 C34 -172.1(2) . . . . ? S31 C31 N32 C34 5.5(3) . . . . ? C31 N32 C32 C33 0.0(3) . . . . ? C34 N32 C32 C33 171.7(2) . . . . ? N32 C32 C33 N31 0.4(3) . . . . ? C31 N31 C33 C32 -0.6(2) . . . . ? B2 N31 C33 C32 -161.3(2) . . . . ? C31 N32 C34 C36 101.3(3) . . . . ? C32 N32 C34 C36 -68.9(3) . . . . ? C31 N32 C34 C35 -133.7(2) . . . . ? C32 N32 C34 C35 56.1(3) . . . . ? N31 B2 S41 C41 -121.43(13) . . . . ? C2 B2 S41 C41 110.01(15) . . . . ? B1 B2 S41 C41 -7.02(13) . . . . ? C1 B1 N41 C41 -118.47(18) . . . . ? B2 B1 N41 C41 -1.2(2) . . . . ? S31 B1 N41 C41 111.64(16) . . . . ? C1 B1 N41 C43 48.3(3) . . . . ? B2 B1 N41 C43 165.6(2) . . . . ? S31 B1 N41 C43 -81.6(3) . . . . ? C43 N41 C41 N42 1.0(2) . . . . ? B1 N41 C41 N42 171.33(16) . . . . ? C43 N41 C41 S41 -175.59(15) . . . . ? B1 N41 C41 S41 -5.3(2) . . . . ? B2 S41 C41 N41 7.80(17) . . . . ? B2 S41 C41 N42 -168.13(19) . . . . ? N41 C41 N42 C42 -0.8(2) . . . . ? S41 C41 N42 C42 175.51(16) . . . . ? N41 C41 N42 C44 -176.4(2) . . . . ? S41 C41 N42 C44 -0.1(3) . . . . ? C41 N42 C42 C43 0.3(3) . . . . ? C44 N42 C42 C43 175.8(2) . . . . ? N42 C42 C43 N41 0.3(3) . . . . ? C41 N41 C43 C42 -0.8(2) . . . . ? B1 N41 C43 C42 -168.4(2) . . . . ? C41 N42 C44 C46 113.3(3) . . . . ? C42 N42 C44 C46 -61.4(3) . . . . ? C41 N42 C44 C45 -122.5(3) . . . . ? C42 N42 C44 C45 62.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.272 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.045 data_wa1320 _database_code_depnum_ccdc_archive 'CCDC 873318' #TrackingRef 'deposit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H10 N2 S' _chemical_formula_sum 'C6 H10 N2 S' _chemical_formula_weight 142.22 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 10.5400(8) _cell_length_b 10.0952(6) _cell_length_c 14.5231(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.236(7) _cell_angle_gamma 90.00 _cell_volume 1541.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10331 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 25.9 _exptl_crystal_description needle _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9002 _exptl_absorpt_correction_T_max 0.9390 _exptl_absorpt_process_details 'MULABS (Spek, 2003; Blessing, 1995)' _exptl_special_details ; ; _diffrn_ambient_temperature 173(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 'STOE IPDS II two-circle-diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 10324 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.59 _reflns_number_total 2880 _reflns_number_gt 2406 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_cell_refinement 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction 'X-Area (Stoe & Cie, 2001)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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. ; _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^)+(0.0556P)^2^+0.1290P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0094(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2880 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0919 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _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 S1 S 0.33594(4) 0.13532(4) 0.03475(3) 0.03018(15) Uani 1 1 d . . . N1 N 0.59498(13) 0.15591(14) 0.04897(11) 0.0297(3) Uani 1 1 d . . . H1 H 0.6086(19) 0.083(2) 0.0234(15) 0.035(5) Uiso 1 1 d . . . N2 N 0.50300(12) 0.31051(14) 0.12148(11) 0.0304(3) Uani 1 1 d . . . C1 C 0.47978(14) 0.20147(15) 0.06940(12) 0.0247(3) Uani 1 1 d . . . C2 C 0.63355(16) 0.33183(18) 0.13347(15) 0.0392(5) Uani 1 1 d . . . H2 H 0.6749 0.4021 0.1673 0.047 Uiso 1 1 calc R . . C3 C 0.69016(15) 0.23550(17) 0.08868(15) 0.0367(4) Uani 1 1 d . . . H3 H 0.7791 0.2240 0.0849 0.044 Uiso 1 1 calc R . . C4 C 0.40535(17) 0.39457(19) 0.15967(15) 0.0388(4) Uani 1 1 d . . . H4 H 0.3215 0.3489 0.1482 0.047 Uiso 1 1 calc R . . C5 C 0.4316(3) 0.4090(4) 0.2628(2) 0.0793(9) Uani 1 1 d . . . H5A H 0.4347 0.3211 0.2915 0.119 Uiso 1 1 calc R . . H5B H 0.3637 0.4613 0.2877 0.119 Uiso 1 1 calc R . . H5C H 0.5133 0.4539 0.2760 0.119 Uiso 1 1 calc R . . C6 C 0.3973(3) 0.5248(3) 0.1097(3) 0.0871(10) Uani 1 1 d . . . H6A H 0.3798 0.5090 0.0434 0.131 Uiso 1 1 calc R . . H6B H 0.4782 0.5722 0.1204 0.131 Uiso 1 1 calc R . . H6C H 0.3286 0.5781 0.1326 0.131 Uiso 1 1 calc R . . S1A S 1.04681(4) 0.34686(4) 0.10695(3) 0.03212(15) Uani 1 1 d . . . N1A N 0.88395(13) 0.55869(14) 0.09781(11) 0.0277(3) Uani 1 1 d . . . H1A H 0.8942(18) 0.5727(19) 0.0422(16) 0.031(5) Uiso 1 1 d . . . N2A N 0.90897(12) 0.47179(13) 0.23382(9) 0.0237(3) Uani 1 1 d . . . C1A C 0.94557(14) 0.46073(16) 0.14638(11) 0.0245(3) Uani 1 1 d . . . C2A C 0.82640(14) 0.57877(15) 0.23923(12) 0.0258(3) Uani 1 1 d . . . H2A H 0.7882 0.6085 0.2927 0.031 Uiso 1 1 calc R . . C3A C 0.81116(15) 0.63197(16) 0.15415(13) 0.0282(4) Uani 1 1 d . . . H3A H 0.7598 0.7063 0.1363 0.034 Uiso 1 1 calc R . . C4A C 0.95697(16) 0.38723(17) 0.31173(12) 0.0297(4) Uani 1 1 d . . . H4A H 1.0046 0.3119 0.2858 0.036 Uiso 1 1 calc R . . C5A C 1.0495(2) 0.4650(2) 0.37483(18) 0.0627(7) Uani 1 1 d . . . H5A1 H 1.1181 0.4992 0.3394 0.094 Uiso 1 1 calc R . . H5A2 H 1.0855 0.4072 0.4243 0.094 Uiso 1 1 calc R . . H5A3 H 1.0051 0.5392 0.4018 0.094 Uiso 1 1 calc R . . C6A C 0.8488(2) 0.3298(3) 0.3610(2) 0.0649(7) Uani 1 1 d . . . H6A1 H 0.7924 0.2797 0.3170 0.097 Uiso 1 1 calc R . . H6A2 H 0.8008 0.4016 0.3876 0.097 Uiso 1 1 calc R . . H6A3 H 0.8827 0.2706 0.4103 0.097 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 S1 0.0231(2) 0.0299(2) 0.0371(3) -0.00929(17) -0.00068(16) -0.00157(15) N1 0.0255(7) 0.0238(7) 0.0399(9) -0.0069(6) 0.0028(6) 0.0011(5) N2 0.0237(7) 0.0259(7) 0.0410(9) -0.0086(6) -0.0007(6) 0.0002(5) C1 0.0248(7) 0.0215(8) 0.0276(9) -0.0005(6) 0.0001(6) 0.0016(6) C2 0.0261(8) 0.0321(9) 0.0584(13) -0.0126(9) -0.0047(8) -0.0040(7) C3 0.0233(8) 0.0313(9) 0.0550(12) -0.0058(8) -0.0011(7) -0.0010(7) C4 0.0306(8) 0.0339(9) 0.0522(12) -0.0182(9) 0.0054(8) 0.0016(7) C5 0.0653(16) 0.119(3) 0.0552(16) -0.0314(17) 0.0123(13) 0.0096(16) C6 0.0862(19) 0.0538(15) 0.126(3) 0.0134(17) 0.0377(18) 0.0399(15) S1A 0.0336(2) 0.0337(3) 0.0298(3) 0.00559(17) 0.00767(17) 0.00973(17) N1A 0.0295(7) 0.0284(7) 0.0254(8) 0.0060(6) 0.0025(6) 0.0024(5) N2A 0.0242(6) 0.0224(6) 0.0242(7) 0.0004(5) -0.0002(5) 0.0011(5) C1A 0.0231(7) 0.0246(8) 0.0256(8) 0.0033(6) 0.0008(6) -0.0034(6) C2A 0.0267(7) 0.0209(8) 0.0294(9) -0.0033(6) 0.0002(6) 0.0004(6) C3A 0.0278(8) 0.0218(8) 0.0348(9) 0.0011(7) 0.0001(7) 0.0008(6) C4A 0.0341(8) 0.0307(8) 0.0240(8) 0.0042(7) -0.0005(6) 0.0078(7) C5A 0.0738(16) 0.0551(14) 0.0532(15) -0.0061(11) -0.0359(12) 0.0088(12) C6A 0.0534(13) 0.0746(17) 0.0680(17) 0.0455(14) 0.0128(11) 0.0073(12) _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 S1 C1 1.6984(15) . ? N1 C1 1.352(2) . ? N1 C3 1.378(2) . ? N1 H1 0.84(2) . ? N2 C1 1.348(2) . ? N2 C2 1.391(2) . ? N2 C4 1.474(2) . ? C2 C3 1.335(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C6 1.501(3) . ? C4 C5 1.509(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? S1A C1A 1.6965(17) . ? N1A C1A 1.353(2) . ? N1A C3A 1.378(2) . ? N1A H1A 0.83(2) . ? N2A C1A 1.359(2) . ? N2A C2A 1.393(2) . ? N2A C4A 1.477(2) . ? C2A C3A 1.346(2) . ? C2A H2A 0.9500 . ? C3A H3A 0.9500 . ? C4A C6A 1.506(3) . ? C4A C5A 1.509(3) . ? C4A H4A 1.0000 . ? C5A H5A1 0.9800 . ? C5A H5A2 0.9800 . ? C5A H5A3 0.9800 . ? C6A H6A1 0.9800 . ? C6A H6A2 0.9800 . ? C6A H6A3 0.9800 . ? 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 C1 N1 C3 110.35(14) . . ? C1 N1 H1 125.4(14) . . ? C3 N1 H1 123.5(13) . . ? C1 N2 C2 109.49(14) . . ? C1 N2 C4 125.36(13) . . ? C2 N2 C4 125.15(15) . . ? N2 C1 N1 105.80(13) . . ? N2 C1 S1 127.48(12) . . ? N1 C1 S1 126.72(13) . . ? C3 C2 N2 107.45(15) . . ? C3 C2 H2 126.3 . . ? N2 C2 H2 126.3 . . ? C2 C3 N1 106.91(14) . . ? C2 C3 H3 126.5 . . ? N1 C3 H3 126.5 . . ? N2 C4 C6 109.78(18) . . ? N2 C4 C5 110.31(18) . . ? C6 C4 C5 113.3(2) . . ? N2 C4 H4 107.8 . . ? C6 C4 H4 107.8 . . ? C5 C4 H4 107.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1A N1A C3A 110.47(15) . . ? C1A N1A H1A 122.4(14) . . ? C3A N1A H1A 127.0(14) . . ? C1A N2A C2A 109.76(13) . . ? C1A N2A C4A 124.32(13) . . ? C2A N2A C4A 125.82(14) . . ? N1A C1A N2A 105.59(14) . . ? N1A C1A S1A 127.52(13) . . ? N2A C1A S1A 126.88(12) . . ? C3A C2A N2A 106.88(15) . . ? C3A C2A H2A 126.6 . . ? N2A C2A H2A 126.6 . . ? C2A C3A N1A 107.28(14) . . ? C2A C3A H3A 126.4 . . ? N1A C3A H3A 126.4 . . ? N2A C4A C6A 110.96(14) . . ? N2A C4A C5A 109.51(15) . . ? C6A C4A C5A 113.0(2) . . ? N2A C4A H4A 107.7 . . ? C6A C4A H4A 107.7 . . ? C5A C4A H4A 107.7 . . ? C4A C5A H5A1 109.5 . . ? C4A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 109.5 . . ? C4A C5A H5A3 109.5 . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? C4A C6A H6A1 109.5 . . ? C4A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? C4A C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? 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 C2 N2 C1 N1 -0.2(2) . . . . ? C4 N2 C1 N1 179.59(17) . . . . ? C2 N2 C1 S1 -179.39(15) . . . . ? C4 N2 C1 S1 0.4(3) . . . . ? C3 N1 C1 N2 0.5(2) . . . . ? C3 N1 C1 S1 179.61(14) . . . . ? C1 N2 C2 C3 -0.1(2) . . . . ? C4 N2 C2 C3 -179.89(18) . . . . ? N2 C2 C3 N1 0.3(2) . . . . ? C1 N1 C3 C2 -0.5(2) . . . . ? C1 N2 C4 C6 -108.7(2) . . . . ? C2 N2 C4 C6 71.1(3) . . . . ? C1 N2 C4 C5 125.8(2) . . . . ? C2 N2 C4 C5 -54.4(3) . . . . ? C3A N1A C1A N2A 1.01(17) . . . . ? C3A N1A C1A S1A -179.32(12) . . . . ? C2A N2A C1A N1A -1.16(17) . . . . ? C4A N2A C1A N1A -177.66(14) . . . . ? C2A N2A C1A S1A 179.16(11) . . . . ? C4A N2A C1A S1A 2.7(2) . . . . ? C1A N2A C2A C3A 0.90(17) . . . . ? C4A N2A C2A C3A 177.33(14) . . . . ? N2A C2A C3A N1A -0.26(17) . . . . ? C1A N1A C3A C2A -0.47(18) . . . . ? C1A N2A C4A C6A -129.2(2) . . . . ? C2A N2A C4A C6A 54.9(2) . . . . ? C1A N2A C4A C5A 105.4(2) . . . . ? C2A N2A C4A C5A -70.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.84(2) 2.44(2) 3.2838(15) 173.3(19) 3_655 N1A H1A S1A 0.83(2) 2.44(2) 3.2566(16) 167.5(18) 3_765 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.265 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.047