# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Peter Licence' _publ_contact_author_email Peter.licence@nottingham.ac.uk loop_ _publ_author_name P.Licence H.Tadesse A.Blake N.Champness P.Rizkallah J.Warren data_1.2H2O _database_code_depnum_ccdc_archive 'CCDC 864748' #TrackingRef 'Licence.cif' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H28 N4 2+, 2(Br -), 2(H2 O)' _chemical_formula_sum 'C16 H32 Br2 N4 O2' _chemical_formula_weight 472.28 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' Br Br -0.2901 2.4595 '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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.253(3) _cell_length_b 14.658(4) _cell_length_c 16.195(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2197(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8734 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'Hexagonal prism' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 3.705 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 19464 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_av_sigmaI/netI 0.011 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 27.71 _reflns_number_total 2550 _reflns_number_gt 2210 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _refine_special_details ; ; _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^)+(0.0222P)^2^+1.2442P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'N1 methyl H atoms from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotating group; riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0040(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2550 _refine_ls_number_parameters 117 _refine_ls_number_restraints 3 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_gt 0.0481 _refine_ls_R_factor_all 0.0263 _refine_ls_wR_factor_ref 0.0502 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 N1 N 0.19033(14) 0.19332(8) 0.41882(7) 0.0230(3) Uani 1 1 d . . . C1M C 0.2086(2) 0.27737(12) 0.46736(11) 0.0370(4) Uani 1 1 d . . . H1MA H 0.2782 0.3174 0.4397 0.055 Uiso 1 1 calc R . . H1MB H 0.2444 0.2620 0.5226 0.055 Uiso 1 1 calc R . . H1MC H 0.1155 0.3087 0.4721 0.055 Uiso 1 1 calc R . . C2 C 0.23971(16) 0.18083(10) 0.34260(8) 0.0218(3) Uani 1 1 d . . . H2A H 0.2947 0.2235 0.3116 0.026 Uiso 1 1 calc R . . N3 N 0.19893(13) 0.09830(8) 0.31706(7) 0.0204(2) Uani 1 1 d . . . C4 C 0.11935(16) 0.05738(10) 0.37861(9) 0.0253(3) Uani 1 1 d . . . H4A H 0.0761 -0.0014 0.3767 0.030 Uiso 1 1 calc R . . C5 C 0.11450(17) 0.11694(11) 0.44248(9) 0.0264(3) Uani 1 1 d . . . H5A H 0.0675 0.1077 0.4940 0.032 Uiso 1 1 calc R . . C6 C 0.22999(16) 0.05971(11) 0.23467(8) 0.0242(3) Uani 1 1 d . . . H6A H 0.2690 -0.0028 0.2409 0.029 Uiso 1 1 calc R . . H6B H 0.3042 0.0974 0.2068 0.029 Uiso 1 1 calc R . . C7 C 0.09431(16) 0.05691(11) 0.18226(8) 0.0222(3) Uani 1 1 d . . . H7A H 0.0536 0.1192 0.1779 0.027 Uiso 1 1 calc R . . H7B H 0.0214 0.0177 0.2096 0.027 Uiso 1 1 calc R . . C8 C 0.12455(15) 0.02018(10) 0.09588(8) 0.0212(3) Uani 1 1 d . . . H8A H 0.1985 0.0588 0.0688 0.025 Uiso 1 1 calc R . . H8B H 0.1636 -0.0425 0.1001 0.025 Uiso 1 1 calc R . . C9 C -0.01177(16) 0.01908(10) 0.04329(8) 0.0222(3) Uani 1 1 d . . . H9A H -0.0493 0.0821 0.0387 0.027 Uiso 1 1 calc R . . H9B H -0.0862 -0.0180 0.0716 0.027 Uiso 1 1 calc R . . Br1 Br -0.052024(17) -0.164132(11) 0.327008(10) 0.02948(7) Uani 1 1 d . . . O1W O 0.10428(16) -0.23483(12) 0.15178(9) 0.0522(4) Uani 1 1 d D . . H1W H 0.1841(15) -0.2101(17) 0.1557(16) 0.078 Uiso 1 1 d D . . H2W H 0.054(2) -0.2114(19) 0.1889(13) 0.078 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0240(6) 0.0223(6) 0.0226(6) -0.0036(5) -0.0020(5) 0.0020(5) C1M 0.0486(10) 0.0292(8) 0.0332(9) -0.0127(7) 0.0002(8) -0.0018(8) C2 0.0206(7) 0.0226(7) 0.0224(7) -0.0009(5) -0.0029(6) 0.0003(6) N3 0.0199(6) 0.0226(6) 0.0189(6) -0.0022(5) -0.0025(5) 0.0012(5) C4 0.0256(7) 0.0232(7) 0.0272(7) 0.0018(6) -0.0010(6) -0.0034(6) C5 0.0268(8) 0.0291(8) 0.0233(7) 0.0022(6) 0.0019(6) 0.0000(6) C6 0.0218(7) 0.0298(8) 0.0210(7) -0.0073(6) -0.0019(5) 0.0033(6) C7 0.0206(7) 0.0257(7) 0.0204(7) -0.0037(6) -0.0021(5) 0.0025(6) C8 0.0198(7) 0.0242(7) 0.0195(6) -0.0011(5) -0.0010(5) 0.0022(6) C9 0.0210(7) 0.0265(8) 0.0192(7) -0.0031(6) -0.0017(5) 0.0023(6) Br1 0.02725(10) 0.02455(10) 0.03663(10) -0.00295(6) 0.00297(6) 0.00064(6) O1W 0.0403(8) 0.0686(10) 0.0476(8) -0.0179(7) 0.0040(6) -0.0161(8) _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 C2 1.3288(19) . ? N1 C5 1.376(2) . ? N1 C1M 1.471(2) . ? C1M H1MA 0.9800 . ? C1M H1MB 0.9800 . ? C1M H1MC 0.9800 . ? C2 N3 1.3331(18) . ? C2 H2A 0.9500 . ? N3 C4 1.3769(19) . ? N3 C6 1.4774(17) . ? C4 C5 1.354(2) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 C7 1.516(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5249(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5221(19) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C9 1.525(3) 5 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? O1W H1W 0.825(9) . ? O1W H2W 0.832(9) . ? 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 C2 N1 C5 108.78(13) . . ? C2 N1 C1M 124.90(14) . . ? C5 N1 C1M 126.26(13) . . ? N1 C1M H1MA 109.5 . . ? N1 C1M H1MB 109.5 . . ? H1MA C1M H1MB 109.5 . . ? N1 C1M H1MC 109.5 . . ? H1MA C1M H1MC 109.5 . . ? H1MB C1M H1MC 109.5 . . ? N1 C2 N3 108.42(13) . . ? N1 C2 H2A 125.8 . . ? N3 C2 H2A 125.8 . . ? C2 N3 C4 108.78(12) . . ? C2 N3 C6 124.94(13) . . ? C4 N3 C6 126.23(13) . . ? C5 C4 N3 106.85(13) . . ? C5 C4 H4A 126.6 . . ? N3 C4 H4A 126.6 . . ? C4 C5 N1 107.16(13) . . ? C4 C5 H5A 126.4 . . ? N1 C5 H5A 126.4 . . ? N3 C6 C7 110.78(12) . . ? N3 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C6 C7 C8 111.79(12) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C9 C8 C7 111.41(12) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C9 113.58(15) . 5 ? C8 C9 H9A 108.9 . . ? C9 C9 H9A 108.9 5 . ? C8 C9 H9B 108.9 . . ? C9 C9 H9B 108.9 5 . ? H9A C9 H9B 107.7 . . ? H1W O1W H2W 105.0(18) . . ? 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 C5 N1 C2 N3 -0.61(16) . . . . ? C1M N1 C2 N3 -177.80(14) . . . . ? N1 C2 N3 C4 0.81(16) . . . . ? N1 C2 N3 C6 178.54(12) . . . . ? C2 N3 C4 C5 -0.70(17) . . . . ? C6 N3 C4 C5 -178.39(13) . . . . ? N3 C4 C5 N1 0.32(17) . . . . ? C2 N1 C5 C4 0.17(17) . . . . ? C1M N1 C5 C4 177.31(15) . . . . ? C2 N3 C6 C7 -107.43(16) . . . . ? C4 N3 C6 C7 69.91(18) . . . . ? N3 C6 C7 C8 178.14(12) . . . . ? C6 C7 C8 C9 -179.07(13) . . . . ? C7 C8 C9 C9 -178.73(15) . . . 5 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.41 _refine_diff_density_min -0.29 _refine_diff_density_rms 0.05 #===END of CIF data_2 _database_code_depnum_ccdc_archive 'CCDC 864749' #TrackingRef 'Licence.cif' _refine_special_details ; Disorder was present in one part of the molecule and was modelled by allowing two orientations with occupancies 0.566(10) for C6 and 0.434(10) for C6'. ; _audit_creation_method 'enCIFer eding of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H32 N4 2+, 2(Br -)' _chemical_formula_sum 'C18 H32 Br2 N4' _chemical_formula_weight 464.30 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3281(7) _cell_length_b 12.8100(12) _cell_length_c 11.3249(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.503(2) _cell_angle_gamma 90.00 _cell_volume 1058.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3376 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 3.838 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details '(Bruker SHELXTL; Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6672 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_av_sigmaI/netI 0.014 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2419 _reflns_number_gt 2110 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'MERCURY (Bruno et al., 2006)' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _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^)+(0.033P)^2^+0.733P] 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 2419 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _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 0.09472(3) 0.27839(2) 0.30283(2) 0.04339(10) Uani 1 1 d . . . N1 N -0.2663(3) 0.4503(2) 0.49037(18) 0.0548(6) Uani 1 1 d . . . C2 C -0.3470(3) 0.3943(2) 0.4005(2) 0.0406(5) Uani 1 1 d . A . N3 N -0.4057(2) 0.46175(14) 0.31529(14) 0.0287(4) Uani 1 1 d . . . C4 C -0.3603(3) 0.56179(18) 0.3529(2) 0.0372(5) Uani 1 1 d . A . H4A H -0.3857 0.6243 0.3093 0.045 Uiso 1 1 calc R . . C5 C -0.2741(3) 0.5545(3) 0.4619(2) 0.0536(7) Uani 1 1 d . A . H5A H -0.2271 0.6107 0.5104 0.064 Uiso 1 1 calc R . . C6 C -0.1794(5) 0.4285(5) 0.6097(4) 0.0363(14) Uiso 0.566(12) 1 d P A 1 H6A H -0.2633 0.3876 0.6538 0.054 Uiso 0.566(12) 1 calc PR A 1 H6B H -0.1505 0.4944 0.6512 0.054 Uiso 0.566(12) 1 calc PR A 1 H6C H -0.0662 0.3888 0.6039 0.054 Uiso 0.566(12) 1 calc PR A 1 C6' C -0.1766(7) 0.3771(6) 0.5906(5) 0.0384(18) Uiso 0.434(12) 1 d P A 2 H6D H -0.2727 0.3388 0.6266 0.058 Uiso 0.434(12) 1 calc PR A 2 H6E H -0.1066 0.4194 0.6513 0.058 Uiso 0.434(12) 1 calc PR A 2 H6F H -0.0943 0.3276 0.5565 0.058 Uiso 0.434(12) 1 calc PR A 2 C7 C -0.3728(4) 0.2808(2) 0.3976(4) 0.0699(10) Uani 1 1 d . . . H7A H -0.4923 0.2642 0.3552 0.105 Uiso 1 1 calc R A . H7B H -0.3681 0.2540 0.4789 0.105 Uiso 1 1 calc R . . H7C H -0.2755 0.2483 0.3567 0.105 Uiso 1 1 calc R . . C8 C -0.4897(3) 0.43516(19) 0.19624(19) 0.0358(5) Uani 1 1 d . A . H8A H -0.5581 0.4963 0.1616 0.043 Uiso 1 1 calc R . . H8B H -0.5779 0.3773 0.2020 0.043 Uiso 1 1 calc R . . C9 C -0.3444(3) 0.40272(18) 0.11526(19) 0.0363(5) Uani 1 1 d . . . H9A H -0.2739 0.3432 0.1519 0.044 Uiso 1 1 calc R A . H9B H -0.4063 0.3786 0.0386 0.044 Uiso 1 1 calc R . . C10 C -0.2121(3) 0.49002(17) 0.09199(18) 0.0317(4) Uani 1 1 d . A . H10A H -0.1519 0.5152 0.1687 0.038 Uiso 1 1 calc R . . H10B H -0.2821 0.5490 0.0536 0.038 Uiso 1 1 calc R . . C11 C -0.0651(3) 0.45606(17) 0.01308(18) 0.0326(4) Uani 1 1 d . . . H11A H 0.0068 0.3982 0.0524 0.039 Uiso 1 1 calc R A . H11B H -0.1255 0.4292 -0.0628 0.039 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 0.03363(13) 0.05510(16) 0.04172(14) -0.00212(11) 0.00501(9) -0.00853(10) N1 0.0240(9) 0.110(2) 0.0309(10) 0.0232(12) 0.0067(8) -0.0079(11) C2 0.0224(9) 0.0541(14) 0.0473(13) 0.0226(11) 0.0135(9) 0.0019(9) N3 0.0252(8) 0.0333(9) 0.0287(9) 0.0045(7) 0.0081(6) -0.0013(7) C4 0.0368(11) 0.0403(12) 0.0374(12) -0.0050(9) 0.0185(9) -0.0072(9) C5 0.0404(13) 0.088(2) 0.0351(12) -0.0137(13) 0.0187(10) -0.0280(13) C7 0.0472(15) 0.0517(16) 0.116(3) 0.0440(18) 0.0354(17) 0.0089(13) C8 0.0257(9) 0.0494(12) 0.0324(11) -0.0036(9) 0.0034(8) -0.0042(9) C9 0.0321(10) 0.0427(12) 0.0348(11) -0.0110(9) 0.0067(8) -0.0032(9) C10 0.0298(9) 0.0394(11) 0.0270(10) -0.0054(9) 0.0085(8) 0.0024(9) C11 0.0323(10) 0.0384(11) 0.0283(10) -0.0067(8) 0.0095(8) 0.0047(9) _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 C2 1.336(4) . ? N1 C5 1.373(4) . ? N1 C6 1.464(4) . ? N1 C6' 1.567(6) . ? C2 N3 1.336(3) . ? C2 C7 1.466(4) . ? N3 C4 1.381(3) . ? N3 C8 1.467(3) . ? C4 C5 1.334(4) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C6' H6D 0.9800 . ? C6' H6E 0.9800 . ? C6' H6F 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.528(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.519(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.528(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C11 1.523(4) 3_565 ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 C2 N1 C5 109.7(2) . . ? C2 N1 C6 136.2(3) . . ? C5 N1 C6 114.0(3) . . ? C2 N1 C6' 110.8(4) . . ? C5 N1 C6' 139.2(4) . . ? N3 C2 N1 106.9(2) . . ? N3 C2 C7 126.4(3) . . ? N1 C2 C7 126.6(3) . . ? C2 N3 C4 109.03(19) . . ? C2 N3 C8 126.2(2) . . ? C4 N3 C8 124.50(18) . . ? C5 C4 N3 107.4(2) . . ? C5 C4 H4A 126.3 . . ? N3 C4 H4A 126.3 . . ? C4 C5 N1 106.9(2) . . ? C4 C5 H5A 126.5 . . ? N1 C5 H5A 126.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? N1 C6' H6D 109.5 . . ? N1 C6' H6E 109.5 . . ? H6D C6' H6E 109.5 . . ? N1 C6' H6F 109.5 . . ? H6D C6' H6F 109.5 . . ? H6E C6' H6F 109.5 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C9 111.07(16) . . ? N3 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? N3 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C10 C9 C8 113.38(18) . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C11 112.91(17) . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C11 C11 C10 113.2(2) 3_565 . ? C11 C11 H11A 108.9 3_565 . ? C10 C11 H11A 108.9 . . ? C11 C11 H11B 108.9 3_565 . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.8 . . ? 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 C5 N1 C2 N3 0.0(2) . . . . ? C6 N1 C2 N3 177.7(3) . . . . ? C6' N1 C2 N3 -174.8(3) . . . . ? C5 N1 C2 C7 -177.7(2) . . . . ? C6 N1 C2 C7 -0.1(5) . . . . ? C6' N1 C2 C7 7.4(4) . . . . ? N1 C2 N3 C4 0.1(2) . . . . ? C7 C2 N3 C4 177.9(2) . . . . ? N1 C2 N3 C8 174.82(17) . . . . ? C7 C2 N3 C8 -7.4(3) . . . . ? C2 N3 C4 C5 -0.2(2) . . . . ? C8 N3 C4 C5 -175.04(18) . . . . ? N3 C4 C5 N1 0.2(2) . . . . ? C2 N1 C5 C4 -0.2(3) . . . . ? C6 N1 C5 C4 -178.4(2) . . . . ? C6' N1 C5 C4 172.5(4) . . . . ? C2 N3 C8 C9 -78.5(2) . . . . ? C4 N3 C8 C9 95.4(2) . . . . ? N3 C8 C9 C10 -64.2(2) . . . . ? C8 C9 C10 C11 178.79(18) . . . . ? C9 C10 C11 C11 178.6(2) . . . 3_565 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.56 _refine_diff_density_min -0.47 _refine_diff_density_rms 0.06 #===END of CIF data_3 _database_code_depnum_ccdc_archive 'CCDC 864750' #TrackingRef 'Licence.cif' _refine_special_details ; Disorder present in unique BF4- by rotation about one B-F direction, modelled over two orientations with similarity restraints aplied to B-F distances. The final occupancies were 0.846(3) and 0.154(3). ; _audit_creation_method 'enCIFer eding of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H32 N4 2+, 2(BF4 -)' _chemical_formula_sum 'C18 H32 N4 B2 F8' _chemical_formula_weight 478.10 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.1057(5) _cell_length_b 14.4418(13) _cell_length_c 13.3895(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.981(2) _cell_angle_gamma 90.00 _cell_volume 1171.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4597 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 29.1 _exptl_crystal_description lozenge _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method ? _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.854 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6703 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 14627 _diffrn_reflns_av_R_equivalents 0.060 _diffrn_reflns_av_sigmaI/netI 0.062 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 31.05 _reflns_number_total 4328 _reflns_number_gt 3228 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 version 2.0-1 (Bruker, 2006)' _computing_cell_refinement 'Bruker SAINT version 7.23A (Bruker, 2006)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'MERCURY (Bruno et al., 2006)' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _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^)+(0.171P)^2^+0.153P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'methyl H atoms from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotor; riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.15(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4173 _refine_ls_number_parameters 176 _refine_ls_number_restraints 65 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.271 _refine_ls_wR_factor_gt 0.255 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.14 _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 N1 N 0.3568(2) 0.06139(9) 0.84443(9) 0.0372(3) Uani 1 1 d U . . C1M C 0.1519(3) 0.21323(15) 0.83378(15) 0.0572(5) Uani 1 1 d U . . H1MA H 0.1209 0.2506 0.8915 0.086 Uiso 1 1 calc R . . H1MB H 0.0218 0.1760 0.8099 0.086 Uiso 1 1 calc R . . H1MC H 0.1876 0.2542 0.7797 0.086 Uiso 1 1 calc R . . N2 N 0.5296(2) 0.17730(9) 0.91736(9) 0.0388(3) Uani 1 1 d U . . C2M C 0.5832(4) 0.27098(15) 0.95405(16) 0.0637(6) Uani 1 1 d U . . H2MA H 0.6255 0.3090 0.8989 0.095 Uiso 1 1 calc R . . H2MB H 0.7060 0.2684 1.0084 0.095 Uiso 1 1 calc R . . H2MC H 0.4540 0.2984 0.9795 0.095 Uiso 1 1 calc R . . C1 C 0.3405(2) 0.15147(10) 0.86431(10) 0.0356(3) Uani 1 1 d U . . C8 C 0.4036(3) 0.00015(10) 0.63383(11) 0.0409(4) Uani 1 1 d U . . H8A H 0.5148 0.0452 0.6639 0.049 Uiso 1 1 calc R . . H8B H 0.4545 -0.0626 0.6556 0.049 Uiso 1 1 calc R . . C5 C 0.5625(3) 0.03082(11) 0.88538(12) 0.0439(4) Uani 1 1 d U . . H5A H 0.6181 -0.0304 0.8816 0.053 Uiso 1 1 calc R . . C9 C 0.3890(3) 0.00604(12) 0.52025(11) 0.0444(4) Uani 1 1 d U . . H9A H 0.3264 0.0670 0.4982 0.053 Uiso 1 1 calc R . . H9B H 0.2861 -0.0423 0.4904 0.053 Uiso 1 1 calc R . . C3 C 0.6688(2) 0.10259(13) 0.93107(11) 0.0446(4) Uani 1 1 d U . . H3A H 0.8135 0.1021 0.9664 0.053 Uiso 1 1 calc R . . C7 C 0.1851(3) 0.01965(17) 0.67299(15) 0.0563(5) Uani 1 1 d U . . H7A H 0.0703 -0.0206 0.6369 0.068 Uiso 1 1 calc R . . H7B H 0.1428 0.0847 0.6575 0.068 Uiso 1 1 calc R . . C6 C 0.1898(3) 0.00385(15) 0.78546(15) 0.0581(5) Uani 1 1 d U . . H6A H 0.0427 0.0182 0.8055 0.070 Uiso 1 1 calc R . . H6B H 0.2214 -0.0622 0.8007 0.070 Uiso 1 1 calc R . . B1 B 0.1449(3) 0.20929(12) 0.14612(13) 0.0418(4) Uani 1 1 d DU . . F1 F 0.1355(3) 0.15154(11) 0.06347(9) 0.0730(5) Uani 1 1 d DU A . F2 F 0.2469(5) 0.16321(13) 0.22878(14) 0.0734(7) Uani 0.808(4) 1 d PDU A 1 F3 F -0.0743(3) 0.22635(17) 0.16134(19) 0.0882(8) Uani 0.808(4) 1 d PDU A 1 F4 F 0.2473(4) 0.29286(13) 0.1352(2) 0.0794(7) Uani 0.808(4) 1 d PDU A 1 F2' F 0.3779(9) 0.1880(6) 0.1572(8) 0.085(3) Uani 0.192(4) 1 d PDU A 2 F3' F 0.096(3) 0.1802(12) 0.2347(7) 0.127(6) Uani 0.192(4) 1 d PDU A 2 F4' F 0.130(2) 0.2867(6) 0.0878(9) 0.094(3) Uani 0.192(4) 1 d PDU A 2 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 0.0398(6) 0.0418(6) 0.0313(5) 0.0000(4) 0.0092(4) -0.0051(4) C1M 0.0508(9) 0.0704(12) 0.0527(10) 0.0217(9) 0.0157(8) 0.0238(8) N2 0.0421(6) 0.0461(6) 0.0292(5) -0.0036(4) 0.0091(4) -0.0051(5) C2M 0.0869(15) 0.0563(10) 0.0518(10) -0.0210(8) 0.0251(10) -0.0240(10) C1 0.0354(6) 0.0433(7) 0.0292(6) 0.0042(5) 0.0088(5) 0.0020(5) C8 0.0490(8) 0.0401(7) 0.0317(6) -0.0024(5) -0.0024(6) -0.0038(5) C5 0.0481(8) 0.0467(8) 0.0391(7) 0.0082(6) 0.0141(6) 0.0113(6) C9 0.0512(8) 0.0485(8) 0.0311(6) -0.0043(5) -0.0050(6) 0.0026(6) C3 0.0349(6) 0.0683(10) 0.0306(6) 0.0047(6) 0.0049(5) 0.0044(6) C7 0.0441(8) 0.0780(12) 0.0451(9) -0.0157(8) -0.0013(6) -0.0153(8) C6 0.0567(10) 0.0711(12) 0.0489(9) -0.0130(8) 0.0164(8) -0.0306(9) B1 0.0391(7) 0.0482(9) 0.0376(8) 0.0007(6) 0.0025(6) -0.0019(6) F1 0.0781(9) 0.0983(11) 0.0398(6) -0.0146(6) -0.0043(6) 0.0260(7) F2 0.1060(17) 0.0655(10) 0.0415(9) 0.0053(7) -0.0198(10) -0.0005(10) F3 0.0501(9) 0.1140(17) 0.1069(17) -0.0276(13) 0.0352(10) 0.0038(9) F4 0.0742(13) 0.0582(10) 0.1040(18) 0.0215(10) 0.0032(12) -0.0159(8) F2' 0.047(3) 0.085(5) 0.115(7) -0.033(5) -0.023(4) 0.001(3) F3' 0.165(14) 0.168(12) 0.056(5) -0.008(6) 0.047(8) -0.050(12) F4' 0.116(9) 0.057(4) 0.108(8) 0.018(4) 0.011(7) 0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3340(19) . ? N1 C5 1.381(2) . ? N1 C6 1.469(2) . ? C1M C1 1.475(2) . ? C1M H1MA 0.9800 . ? C1M H1MB 0.9800 . ? C1M H1MC 0.9800 . ? N2 C1 1.3329(19) . ? N2 C3 1.372(2) . ? N2 C2M 1.463(2) . ? C2M H2MA 0.9800 . ? C2M H2MB 0.9800 . ? C2M H2MC 0.9800 . ? C8 C9 1.515(2) . ? C8 C7 1.518(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C5 C3 1.332(3) . ? C5 H5A 0.9500 . ? C9 C9 1.530(3) 3_656 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C3 H3A 0.9500 . ? C7 C6 1.520(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? B1 F1 1.381(2) . ? B1 F2 1.374(2) . ? B1 F3 1.400(2) . ? B1 F4 1.375(2) . ? B1 F2' 1.446(5) . ? B1 F3' 1.325(6) . ? B1 F4' 1.361(6) . ? 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 C5 108.59(13) . . ? C1 N1 C6 126.54(15) . . ? C5 N1 C6 124.83(15) . . ? C1 C1M H1MA 109.5 . . ? C1 C1M H1MB 109.5 . . ? H1MA C1M H1MB 109.5 . . ? C1 C1M H1MC 109.5 . . ? H1MA C1M H1MC 109.5 . . ? H1MB C1M H1MC 109.5 . . ? C1 N2 C3 109.49(13) . . ? C1 N2 C2M 125.58(17) . . ? C3 N2 C2M 124.93(16) . . ? N2 C2M H2MA 109.5 . . ? N2 C2M H2MB 109.5 . . ? H2MA C2M H2MB 109.5 . . ? N2 C2M H2MC 109.5 . . ? H2MA C2M H2MC 109.5 . . ? H2MB C2M H2MC 109.5 . . ? N2 C1 N1 107.38(13) . . ? N2 C1 C1M 125.10(16) . . ? N1 C1 C1M 127.52(15) . . ? C9 C8 C7 112.91(14) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C3 C5 N1 107.63(14) . . ? C3 C5 H5A 126.2 . . ? N1 C5 H5A 126.2 . . ? C8 C9 C9 113.74(16) . 3_656 ? C8 C9 H9A 108.8 . . ? C9 C9 H9A 108.8 3_656 . ? C8 C9 H9B 108.8 . . ? C9 C9 H9B 108.8 3_656 . ? H9A C9 H9B 107.7 . . ? C5 C3 N2 106.91(14) . . ? C5 C3 H3A 126.5 . . ? N2 C3 H3A 126.5 . . ? C8 C7 C6 113.78(17) . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N1 C6 C7 112.06(14) . . ? N1 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N1 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? F1 B1 F2 108.87(16) . . ? F1 B1 F3 106.01(15) . . ? F1 B1 F4 114.81(19) . . ? F2 B1 F3 108.4(2) . . ? F2 B1 F4 110.1(2) . . ? F3 B1 F4 108.42(19) . . ? F1 B1 F2' 84.2(4) . . ? F1 B1 F3' 122.2(7) . . ? F1 B1 F4' 92.5(5) . . ? F2' B1 F3' 99.5(10) . . ? F2' B1 F4' 103.2(7) . . ? F3' B1 F4' 140.2(10) . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.45 _refine_diff_density_min -0.41 _refine_diff_density_rms 0.07 #===END of CIF data_4.1.2(C7H8) _database_code_depnum_ccdc_archive 'CCDC 864751' #TrackingRef 'Licence.cif' _refine_special_details ; The solvent region could not be modelled in terms of discrete atomic sites, so PLATON SQUEEZE was used to model the contribution of the diffuse toluene solvent to the diffraction pattern and thereby produce a set of solvent-free diffraction intensities which were used for all subsequent refinement. The analysis gave a solvent volume of 571 cubic Angstroms and the electron count/cell was 121. The number of toluene molecules per cell was calculated to be 2.4 and these are included in the chemical formula. Methyl H atoms from delta-F and others placed geometrically ; loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.023 -0.024 0.500 571 121 ' ' _platon_squeeze_details ; ? ; _audit_creation_method 'enCIFer eding of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H36 N4 2+, 2(Br-), 1.2(C7 H8)' _chemical_formula_sum 'C28.4 H45.6 Br2 N4' _chemical_formula_weight 602.91 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.402(2) _cell_length_b 8.826(2) _cell_length_c 23.752(5) _cell_angle_alpha 79.880(2) _cell_angle_beta 86.970(2) _cell_angle_gamma 63.148(2) _cell_volume 1546.3(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4410 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.040 _exptl_crystal_size_mid 0.032 _exptl_crystal_size_min 0.016 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method ? _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 2.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.571 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS version 2004/1; Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6703 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 17642 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.065 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 30.56 _reflns_number_total 9183 _reflns_number_gt 5377 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 version 2.0-1 (Bruker, 2006)' _computing_cell_refinement 'Bruker SAINT version 7.23A (Bruker, 2006)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'MERCURY (Bruno et al., 2006)' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2003)' _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^)+(0.0597P)^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 SHELXL _refine_ls_extinction_coef 0.0252(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 9183 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.107 _refine_ls_wR_factor_gt 0.100 _refine_ls_goodness_of_fit_ref 0.86 _refine_ls_restrained_S_all 0.86 _refine_ls_shift/su_max 0.009 _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 0.59941(3) 0.58258(3) 0.063430(11) 0.04195(9) Uani 1 1 d . . . Br2 Br 0.04248(4) 1.03745(4) 0.177506(13) 0.05234(10) Uani 1 1 d . . . N1 N 0.6682(3) 1.0838(3) 0.07767(9) 0.0360(4) Uani 1 1 d . . . N2 N 0.5011(3) 1.1194(2) 0.15073(8) 0.0332(4) Uani 1 1 d . . . N1' N 0.1015(3) 0.4316(2) 0.08716(8) 0.0318(4) Uani 1 1 d . . . N2' N 0.0090(3) 0.5944(2) 0.15156(8) 0.0316(4) Uani 1 1 d . . . C2 C 0.6043(3) 1.1759(3) 0.11873(11) 0.0371(5) Uani 1 1 d . . . H2A H 0.6279 1.2677 0.1246 0.045 Uiso 1 1 calc R . . C4 C 0.6063(3) 0.9621(3) 0.08347(11) 0.0403(6) Uani 1 1 d . . . H4A H 0.6325 0.8784 0.0596 0.048 Uiso 1 1 calc R . . C5 C 0.5022(3) 0.9835(3) 0.12907(10) 0.0368(5) Uani 1 1 d . . . H5A H 0.4410 0.9177 0.1437 0.044 Uiso 1 1 calc R . . C1" C 0.4134(3) 1.1803(3) 0.20267(10) 0.0385(5) Uani 1 1 d . . . H1"A H 0.2936 1.1844 0.2036 0.046 Uiso 1 1 calc R . . H1"B H 0.3975 1.2988 0.2020 0.046 Uiso 1 1 calc R . . C1'A C 0.1165(4) 0.3077(3) 0.05118(11) 0.0407(6) Uani 1 1 d . . . H1'A H 0.1451 0.1959 0.0752 0.061 Uiso 1 1 calc R . . H1'B H 0.2113 0.2952 0.0238 0.061 Uiso 1 1 calc R . . H1'C H 0.0029 0.3490 0.0303 0.061 Uiso 1 1 calc R . . C1"A C -0.0822(3) 0.6660(3) 0.20201(10) 0.0351(5) Uani 1 1 d . . . H1"C H -0.2030 0.6726 0.2030 0.042 Uiso 1 1 calc R . . H1"D H -0.0953 0.7844 0.1993 0.042 Uiso 1 1 calc R . . C2"A C 0.0212(3) 0.5560(3) 0.25657(10) 0.0367(5) Uani 1 1 d . . . H2"A H 0.1430 0.5473 0.2550 0.044 Uiso 1 1 calc R . . H2"B H 0.0323 0.4383 0.2595 0.044 Uiso 1 1 calc R . . C3"A C -0.0687(3) 0.6298(3) 0.30935(10) 0.0385(5) Uani 1 1 d . . . H3"A H -0.1926 0.6440 0.3099 0.046 Uiso 1 1 calc R . . H3"B H -0.0743 0.7451 0.3074 0.046 Uiso 1 1 calc R . . C4"A C 0.0307(3) 0.5142(3) 0.36438(10) 0.0411(6) Uani 1 1 d . . . H4"A H 0.0370 0.3987 0.3659 0.049 Uiso 1 1 calc R . . H4"B H 0.1544 0.5004 0.3635 0.049 Uiso 1 1 calc R . . C5"A C -0.0555(4) 0.5828(3) 0.41824(10) 0.0435(6) Uani 1 1 d . . . H5"A H -0.1792 0.5967 0.4191 0.052 Uiso 1 1 calc R . . H5"B H -0.0617 0.6982 0.4168 0.052 Uiso 1 1 calc R . . C6"A C 0.0440(4) 0.4669(3) 0.47321(10) 0.0439(6) Uani 1 1 d . . . H6"A H 0.0529 0.3508 0.4742 0.053 Uiso 1 1 calc R . . H6"B H 0.1669 0.4554 0.4728 0.053 Uiso 1 1 calc R . . C1' C 0.7910(4) 1.1055(4) 0.03435(12) 0.0504(7) Uani 1 1 d . . . H1'D H 0.7729 1.2251 0.0281 0.076 Uiso 1 1 calc R . . H1'E H 0.7678 1.0780 -0.0016 0.076 Uiso 1 1 calc R . . H1'F H 0.9144 1.0280 0.0476 0.076 Uiso 1 1 calc R . . C2" C 0.5199(3) 1.0650(3) 0.25603(11) 0.0393(5) Uani 1 1 d . . . H2"C H 0.6405 1.0592 0.2548 0.047 Uiso 1 1 calc R . . H2"D H 0.5338 0.9470 0.2572 0.047 Uiso 1 1 calc R . . C3" C 0.4291(4) 1.1313(3) 0.30985(10) 0.0423(6) Uani 1 1 d . . . H3"C H 0.3075 1.1395 0.3104 0.051 Uiso 1 1 calc R . . H3"D H 0.4171 1.2486 0.3088 0.051 Uiso 1 1 calc R . . C4" C 0.5317(4) 1.0157(3) 0.36431(11) 0.0442(6) Uani 1 1 d . . . H4"C H 0.5420 0.8989 0.3655 0.053 Uiso 1 1 calc R . . H4"D H 0.6539 1.0059 0.3633 0.053 Uiso 1 1 calc R . . C5" C 0.4442(4) 1.0819(3) 0.41831(11) 0.0434(6) Uani 1 1 d . . . H5"C H 0.3207 1.0953 0.4186 0.052 Uiso 1 1 calc R . . H5"D H 0.4373 1.1972 0.4175 0.052 Uiso 1 1 calc R . . C6" C 0.5425(4) 0.9646(3) 0.47338(11) 0.0444(6) Uani 1 1 d . . . H6"C H 0.5454 0.8505 0.4750 0.053 Uiso 1 1 calc R . . H6"D H 0.6673 0.9476 0.4726 0.053 Uiso 1 1 calc R . . C2A C -0.0070(3) 0.4724(3) 0.13041(10) 0.0337(5) Uani 1 1 d . . . H2AA H -0.0838 0.4223 0.1441 0.040 Uiso 1 1 calc R . . C4A C 0.1349(3) 0.6314(3) 0.12099(10) 0.0362(5) Uani 1 1 d . . . H4AA H 0.1737 0.7129 0.1273 0.043 Uiso 1 1 calc R . . C5A C 0.1927(3) 0.5306(3) 0.08049(10) 0.0357(5) Uani 1 1 d . . . H5AA H 0.2791 0.5279 0.0527 0.043 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 0.04625(16) 0.04632(16) 0.04684(16) -0.01075(11) 0.00529(11) -0.03200(13) Br2 0.06194(19) 0.04898(17) 0.0599(2) -0.00746(14) 0.00591(14) -0.03798(15) N1 0.0394(11) 0.0368(11) 0.0363(11) -0.0054(9) 0.0077(9) -0.0220(9) N2 0.0345(10) 0.0316(10) 0.0340(11) -0.0050(8) 0.0040(8) -0.0159(9) N1' 0.0392(10) 0.0354(10) 0.0281(10) -0.0036(8) -0.0005(8) -0.0235(9) N2' 0.0358(10) 0.0336(10) 0.0285(10) -0.0023(8) -0.0021(8) -0.0190(9) C2 0.0431(13) 0.0350(12) 0.0396(14) -0.0071(10) 0.0087(11) -0.0236(11) C4 0.0488(15) 0.0400(13) 0.0393(14) -0.0082(11) 0.0011(11) -0.0257(12) C5 0.0401(13) 0.0398(13) 0.0384(13) -0.0043(10) 0.0007(10) -0.0257(11) C1" 0.0364(13) 0.0415(13) 0.0333(13) -0.0044(10) 0.0051(10) -0.0149(11) C1'A 0.0538(15) 0.0459(14) 0.0339(13) -0.0113(11) 0.0055(11) -0.0313(13) C1"A 0.0377(12) 0.0360(12) 0.0314(12) -0.0064(10) 0.0018(10) -0.0163(10) C2"A 0.0374(13) 0.0374(13) 0.0337(13) -0.0053(10) 0.0018(10) -0.0156(11) C3"A 0.0397(13) 0.0381(13) 0.0333(13) -0.0064(10) 0.0025(10) -0.0137(11) C4"A 0.0398(13) 0.0420(14) 0.0326(13) -0.0082(11) 0.0024(11) -0.0103(11) C5"A 0.0458(15) 0.0446(14) 0.0314(13) -0.0080(11) 0.0039(11) -0.0124(12) C6"A 0.0471(15) 0.0419(14) 0.0315(13) -0.0059(11) 0.0047(11) -0.0107(12) C1' 0.0514(16) 0.0601(18) 0.0428(16) -0.0110(13) 0.0180(13) -0.0288(14) C2" 0.0387(13) 0.0365(13) 0.0367(13) -0.0048(10) 0.0042(11) -0.0125(11) C3" 0.0443(14) 0.0395(14) 0.0351(14) -0.0071(11) 0.0052(11) -0.0122(12) C4" 0.0444(15) 0.0425(14) 0.0345(14) -0.0066(11) -0.0007(11) -0.0095(12) C5" 0.0449(14) 0.0446(14) 0.0328(13) -0.0064(11) 0.0044(11) -0.0137(12) C6" 0.0435(14) 0.0441(15) 0.0360(14) -0.0085(11) 0.0015(11) -0.0108(12) C2A 0.0341(12) 0.0405(13) 0.0331(12) -0.0037(10) 0.0001(10) -0.0232(11) C4A 0.0472(14) 0.0387(13) 0.0331(13) -0.0030(10) 0.0018(11) -0.0295(12) C5A 0.0403(13) 0.0410(13) 0.0359(13) -0.0035(10) 0.0012(10) -0.0281(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 N1 C2 1.315(3) . ? N1 C4 1.374(3) . ? N1 C1' 1.469(3) . ? N2 C2 1.328(3) . ? N2 C5 1.382(3) . ? N2 C1" 1.461(3) . ? N1' C2A 1.323(3) . ? N1' C5A 1.385(3) . ? N1' C1'A 1.461(3) . ? N2' C2A 1.326(3) . ? N2' C4A 1.378(3) . ? N2' C1"A 1.468(3) . ? C2 H2A 0.9500 . ? C4 C5 1.340(3) . ? C4 H4A 0.9500 . ? C5 H5A 0.9500 . ? C1" C2" 1.512(3) . ? C1" H1"A 0.9900 . ? C1" H1"B 0.9900 . ? C1'A H1'A 0.9800 . ? C1'A H1'B 0.9800 . ? C1'A H1'C 0.9800 . ? C1"A C2"A 1.514(3) . ? C1"A H1"C 0.9900 . ? C1"A H1"D 0.9900 . ? C2"A C3"A 1.520(3) . ? C2"A H2"A 0.9900 . ? C2"A H2"B 0.9900 . ? C3"A C4"A 1.525(3) . ? C3"A H3"A 0.9900 . ? C3"A H3"B 0.9900 . ? C4"A C5"A 1.518(3) . ? C4"A H4"A 0.9900 . ? C4"A H4"B 0.9900 . ? C5"A C6"A 1.524(3) . ? C5"A H5"A 0.9900 . ? C5"A H5"B 0.9900 . ? C6"A C6"A 1.510(5) 2_566 ? C6"A H6"A 0.9900 . ? C6"A H6"B 0.9900 . ? C1' H1'D 0.9800 . ? C1' H1'E 0.9800 . ? C1' H1'F 0.9800 . ? C2" C3" 1.522(3) . ? C2" H2"C 0.9900 . ? C2" H2"D 0.9900 . ? C3" C4" 1.523(3) . ? C3" H3"C 0.9900 . ? C3" H3"D 0.9900 . ? C4" C5" 1.517(4) . ? C4" H4"C 0.9900 . ? C4" H4"D 0.9900 . ? C5" C6" 1.527(3) . ? C5" H5"C 0.9900 . ? C5" H5"D 0.9900 . ? C6" C6" 1.510(5) 2_676 ? C6" H6"C 0.9900 . ? C6" H6"D 0.9900 . ? C2A H2AA 0.9500 . ? C4A C5A 1.347(3) . ? C4A H4AA 0.9500 . ? C5A H5AA 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 C2 N1 C4 108.9(2) . . ? C2 N1 C1' 124.7(2) . . ? C4 N1 C1' 126.3(2) . . ? C2 N2 C5 108.3(2) . . ? C2 N2 C1" 126.1(2) . . ? C5 N2 C1" 125.49(19) . . ? C2A N1' C5A 108.61(19) . . ? C2A N1' C1'A 125.36(19) . . ? C5A N1' C1'A 126.0(2) . . ? C2A N2' C4A 108.4(2) . . ? C2A N2' C1"A 125.03(19) . . ? C4A N2' C1"A 126.40(19) . . ? N1 C2 N2 108.7(2) . . ? N1 C2 H2A 125.6 . . ? N2 C2 H2A 125.6 . . ? C5 C4 N1 107.2(2) . . ? C5 C4 H4A 126.4 . . ? N1 C4 H4A 126.4 . . ? C4 C5 N2 106.9(2) . . ? C4 C5 H5A 126.6 . . ? N2 C5 H5A 126.6 . . ? N2 C1" C2" 111.8(2) . . ? N2 C1" H1"A 109.3 . . ? C2" C1" H1"A 109.3 . . ? N2 C1" H1"B 109.3 . . ? C2" C1" H1"B 109.3 . . ? H1"A C1" H1"B 107.9 . . ? N1' C1'A H1'A 109.5 . . ? N1' C1'A H1'B 109.5 . . ? H1'A C1'A H1'B 109.5 . . ? N1' C1'A H1'C 109.5 . . ? H1'A C1'A H1'C 109.5 . . ? H1'B C1'A H1'C 109.5 . . ? N2' C1"A C2"A 111.11(19) . . ? N2' C1"A H1"C 109.4 . . ? C2"A C1"A H1"C 109.4 . . ? N2' C1"A H1"D 109.4 . . ? C2"A C1"A H1"D 109.4 . . ? H1"C C1"A H1"D 108.0 . . ? C1"A C2"A C3"A 112.0(2) . . ? C1"A C2"A H2"A 109.2 . . ? C3"A C2"A H2"A 109.2 . . ? C1"A C2"A H2"B 109.2 . . ? C3"A C2"A H2"B 109.2 . . ? H2"A C2"A H2"B 107.9 . . ? C2"A C3"A C4"A 111.9(2) . . ? C2"A C3"A H3"A 109.2 . . ? C4"A C3"A H3"A 109.2 . . ? C2"A C3"A H3"B 109.2 . . ? C4"A C3"A H3"B 109.2 . . ? H3"A C3"A H3"B 107.9 . . ? C5"A C4"A C3"A 113.6(2) . . ? C5"A C4"A H4"A 108.8 . . ? C3"A C4"A H4"A 108.8 . . ? C5"A C4"A H4"B 108.8 . . ? C3"A C4"A H4"B 108.8 . . ? H4"A C4"A H4"B 107.7 . . ? C4"A C5"A C6"A 113.5(2) . . ? C4"A C5"A H5"A 108.9 . . ? C6"A C5"A H5"A 108.9 . . ? C4"A C5"A H5"B 108.9 . . ? C6"A C5"A H5"B 108.9 . . ? H5"A C5"A H5"B 107.7 . . ? C6"A C6"A C5"A 113.5(3) 2_566 . ? C6"A C6"A H6"A 108.9 2_566 . ? C5"A C6"A H6"A 108.9 . . ? C6"A C6"A H6"B 108.9 2_566 . ? C5"A C6"A H6"B 108.9 . . ? H6"A C6"A H6"B 107.7 . . ? N1 C1' H1'D 109.5 . . ? N1 C1' H1'E 109.5 . . ? H1'D C1' H1'E 109.5 . . ? N1 C1' H1'F 109.5 . . ? H1'D C1' H1'F 109.5 . . ? H1'E C1' H1'F 109.5 . . ? C1" C2" C3" 111.4(2) . . ? C1" C2" H2"C 109.3 . . ? C3" C2" H2"C 109.3 . . ? C1" C2" H2"D 109.3 . . ? C3" C2" H2"D 109.3 . . ? H2"C C2" H2"D 108.0 . . ? C2" C3" C4" 112.5(2) . . ? C2" C3" H3"C 109.1 . . ? C4" C3" H3"C 109.1 . . ? C2" C3" H3"D 109.1 . . ? C4" C3" H3"D 109.1 . . ? H3"C C3" H3"D 107.8 . . ? C5" C4" C3" 113.1(2) . . ? C5" C4" H4"C 109.0 . . ? C3" C4" H4"C 109.0 . . ? C5" C4" H4"D 109.0 . . ? C3" C4" H4"D 109.0 . . ? H4"C C4" H4"D 107.8 . . ? C4" C5" C6" 113.8(2) . . ? C4" C5" H5"C 108.8 . . ? C6" C5" H5"C 108.8 . . ? C4" C5" H5"D 108.8 . . ? C6" C5" H5"D 108.8 . . ? H5"C C5" H5"D 107.7 . . ? C6" C6" C5" 113.1(3) 2_676 . ? C6" C6" H6"C 109.0 2_676 . ? C5" C6" H6"C 109.0 . . ? C6" C6" H6"D 109.0 2_676 . ? C5" C6" H6"D 109.0 . . ? H6"C C6" H6"D 107.8 . . ? N1' C2A N2' 108.94(19) . . ? N1' C2A H2AA 125.5 . . ? N2' C2A H2AA 125.5 . . ? C5A C4A N2' 107.4(2) . . ? C5A C4A H4AA 126.3 . . ? N2' C4A H4AA 126.3 . . ? C4A C5A N1' 106.7(2) . . ? C4A C5A H5AA 126.7 . . ? N1' C5A H5AA 126.7 . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.54 _refine_diff_density_min -0.66 _refine_diff_density_rms 0.07 #===END of CIF