# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name G.Hughes C.Wang A.S.Batsanov M.Fern S.Frank M.R.Bryce ; I.F.Perepichka ; A.P.Monkman _publ_contact_author_name 'Prof Martin Bryce' _publ_contact_author_address ; Department of Chemistry Durham University Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email M.R.BRYCE@DURHAM.AC.UK _publ_section_title ; New pyrimidine- and fluorene-containing oligo(arylene)s: synthesis, crystal structures, optoelectronic properties and a theoretical study ; data_(6) _database_code_CSD 203937 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-phenyl-5-bromopyrimidine ; _chemical_name_common 2-phenyl-5-bromopyrimidine _chemical_melting_point '104.0--104.5 \%C' _chemical_formula_moiety ? _chemical_formula_sum 'C10 H7 Br N2' _chemical_formula_weight 235.09 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 P2(1)/c 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 6.271(1) _cell_length_b 21.359(3) _cell_length_c 6.932(1) _cell_angle_alpha 90.00 _cell_angle_beta 108.27(1) _cell_angle_gamma 90.00 _cell_volume 881.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 843 _cell_measurement_theta_min 12.00 _cell_measurement_theta_max 24.50 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 4.609 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1486 _exptl_absorpt_correction_T_max 0.8322 _exptl_absorpt_process_details 'XPREP (SHELXTL,1997); R(int)=0.102 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 0.00 0.0200 0.00 -1.00 0.00 0.0200 0.00 0.00 1.00 0.2250 0.00 0.00 -1.00 0.2250 1.00 0.00 0.00 0.3000 -1.00 0.00 1.00 0.2200 1.00 0.00 -1.00 0.2600 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.42 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 10386 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 29.06 _reflns_number_total 2358 _reflns_number_gt 2004 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.060 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.060 (Bruker, 1999)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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. ; _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^)+(0.0372P)^2^+0.7319P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2358 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0786 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Br Br 0.44701(4) 0.324565(10) 0.66886(4) 0.02587(9) Uani 1 1 d . . . N1 N 0.5500(3) 0.51320(9) 0.7701(3) 0.0184(4) Uani 1 1 d . . . C2 C 0.7619(3) 0.51852(9) 0.7635(3) 0.0153(4) Uani 1 1 d . . . N3 N 0.8861(3) 0.47109(8) 0.7279(3) 0.0177(4) Uani 1 1 d . . . C4 C 0.7922(4) 0.41454(10) 0.7006(3) 0.0182(4) Uani 1 1 d . . . H4 H 0.8744 0.3822 0.6794 0.022 Uiso 1 1 d R . . C5 C 0.5766(4) 0.40488(10) 0.7075(3) 0.0178(4) Uani 1 1 d . . . C6 C 0.4580(4) 0.45632(10) 0.7418(4) 0.0198(4) Uani 1 1 d . . . H6 H 0.3070 0.4560 0.7502 0.024 Uiso 1 1 d R . . C11 C 0.8636(3) 0.58173(9) 0.7976(3) 0.0162(4) Uani 1 1 d . . . C12 C 0.7715(4) 0.62791(10) 0.8901(3) 0.0193(4) Uani 1 1 d . . . H12 H 0.6524 0.6185 0.9373 0.023 Uiso 1 1 d R . . C13 C 0.8700(4) 0.68687(10) 0.9282(4) 0.0228(5) Uani 1 1 d . . . H13 H 0.8144 0.7122 0.9954 0.027 Uiso 1 1 d R . . C14 C 1.0568(4) 0.70084(11) 0.8689(4) 0.0252(5) Uani 1 1 d . . . H14 H 1.1112 0.7363 0.8879 0.030 Uiso 1 1 d R . . C15 C 1.1473(4) 0.65495(12) 0.7742(4) 0.0242(5) Uani 1 1 d . . . H15 H 1.2820 0.6651 0.7307 0.029 Uiso 1 1 d R . . C16 C 1.0537(4) 0.59555(10) 0.7414(3) 0.0192(4) Uani 1 1 d . . . H16 H 1.1185 0.5658 0.6800 0.023 Uiso 1 1 d 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 Br 0.02630(14) 0.02004(13) 0.02866(14) -0.00126(9) 0.00486(10) -0.00424(9) N1 0.0144(8) 0.0189(8) 0.0229(9) 0.0017(7) 0.0074(7) 0.0023(7) C2 0.0144(9) 0.0164(9) 0.0148(9) 0.0020(7) 0.0042(8) 0.0020(7) N3 0.0153(8) 0.0181(8) 0.0197(9) 0.0008(7) 0.0057(7) 0.0035(7) C4 0.0194(10) 0.0173(9) 0.0173(10) 0.0007(8) 0.0048(8) 0.0041(8) C5 0.0193(10) 0.0155(9) 0.0166(10) 0.0016(8) 0.0029(8) -0.0014(8) C6 0.0160(10) 0.0211(10) 0.0224(11) 0.0014(8) 0.0063(9) -0.0004(8) C11 0.0141(9) 0.0163(9) 0.0163(10) 0.0029(8) 0.0021(8) 0.0018(7) C12 0.0180(10) 0.0186(10) 0.0202(10) 0.0021(8) 0.0045(8) 0.0035(8) C13 0.0265(12) 0.0161(10) 0.0229(11) 0.0003(8) 0.0034(9) 0.0052(8) C14 0.0258(11) 0.0156(10) 0.0280(13) 0.0030(9) -0.0004(10) -0.0039(9) C15 0.0183(10) 0.0244(11) 0.0284(12) 0.0061(9) 0.0049(9) -0.0014(9) C16 0.0155(10) 0.0203(10) 0.0210(11) 0.0036(8) 0.0044(8) 0.0021(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 Br C5 1.881(2) . ? N1 C6 1.333(3) . ? N1 C2 1.348(3) . ? C2 N3 1.347(3) . ? C2 C11 1.480(3) . ? N3 C4 1.331(3) . ? C4 C5 1.383(3) . ? C5 C6 1.388(3) . ? C11 C12 1.396(3) . ? C11 C16 1.397(3) . ? C12 C13 1.391(3) . ? C13 C14 1.390(3) . ? C14 C15 1.395(4) . ? C15 C16 1.386(3) . ? 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 C6 N1 C2 117.21(18) . . ? N3 C2 N1 125.16(19) . . ? N3 C2 C11 118.03(18) . . ? N1 C2 C11 116.82(18) . . ? C4 N3 C2 116.90(18) . . ? N3 C4 C5 121.62(19) . . ? C4 C5 C6 118.0(2) . . ? C4 C5 Br 120.95(16) . . ? C6 C5 Br 121.03(17) . . ? N1 C6 C5 121.1(2) . . ? C12 C11 C16 119.4(2) . . ? C12 C11 C2 119.88(19) . . ? C16 C11 C2 120.72(18) . . ? C13 C12 C11 120.3(2) . . ? C14 C13 C12 120.2(2) . . ? C13 C14 C15 119.5(2) . . ? C16 C15 C14 120.4(2) . . ? C15 C16 C11 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.602 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.092 #===========================================================END data_(7) _database_code_CSD 203938 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-diphenylpyrimidine ; _chemical_name_common 2,5-diphenylpyrimidine _chemical_melting_point '185.0--185.5 \%C' _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 N2' _chemical_formula_weight 232.28 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M I2/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 7.444(2) _cell_length_b 5.731(2) _cell_length_c 26.932(8) _cell_angle_alpha 90.00 _cell_angle_beta 92.82(1) _cell_angle_gamma 90.00 _cell_volume 1147.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 616 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 25.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection covered almost the full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.54 cm. ; _diffrn_ambient_temperature 103(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 4867 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 29.05 _reflns_number_total 1528 _reflns_number_gt 1263 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'SMART version 5.054 (Bruker, 1998)' _computing_data_reduction 'SAINT version 6.01 (Bruker, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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. ; _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^)+(0.0644P)^2^+0.7255P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1528 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.2440(3) 0.0285(4) 0.02919(7) 0.0167(3) Uiso 0.50 1 d P . 1 C1 C 0.2102(3) 0.0299(4) 0.01828(9) 0.0167(3) Uiso 0.50 1 d P . 2 H1 H 0.241(4) 0.590(5) 0.0383(10) 0.019(6) Uiso 0.50 1 d P A 2 C2 C 0.20376(14) 0.23514(18) 0.04795(4) 0.0164(2) Uani 1 1 d . . . N3 N 0.2043(3) 0.4415(4) 0.02592(8) 0.0162(3) Uiso 0.50 1 d P . 1 C3 C 0.2505(3) 0.4405(4) 0.02149(10) 0.0162(3) Uiso 0.50 1 d P . 2 H3 H 0.183(4) -0.122(5) 0.0350(9) 0.020(7) Uiso 0.50 1 d P B 2 C4 C 0.15481(14) 0.23892(18) 0.10052(4) 0.0162(2) Uani 1 1 d . . . C5 C 0.20313(14) 0.05514(18) 0.13281(4) 0.0181(3) Uani 1 1 d . . . H5 H 0.272(2) -0.076(3) 0.1211(5) 0.027(4) Uiso 1 1 d . . . C6 C 0.16072(15) 0.0650(2) 0.18251(4) 0.0201(3) Uani 1 1 d . . . H6 H 0.198(2) -0.063(3) 0.2045(5) 0.024(4) Uiso 1 1 d . . . C7 C 0.06849(15) 0.2561(2) 0.20051(4) 0.0207(3) Uani 1 1 d . . . H7 H 0.038(2) 0.263(3) 0.2354(6) 0.030(4) Uiso 1 1 d . . . C8 C 0.01845(15) 0.4380(2) 0.16859(4) 0.0205(3) Uani 1 1 d . . . H8 H -0.048(2) 0.572(3) 0.1798(6) 0.030(4) Uiso 1 1 d . . . C9 C 0.06219(15) 0.43064(19) 0.11905(4) 0.0184(3) Uani 1 1 d . . . H9 H 0.026(2) 0.557(3) 0.0964(5) 0.022(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0165(5) 0.0143(5) 0.0184(5) 0.0001(4) 0.0007(4) 0.0009(4) C4 0.0154(5) 0.0152(5) 0.0180(5) -0.0005(4) 0.0009(4) -0.0018(4) C5 0.0168(5) 0.0158(5) 0.0217(5) 0.0006(4) 0.0017(4) 0.0007(4) C6 0.0189(5) 0.0203(5) 0.0209(5) 0.0040(4) 0.0007(4) -0.0005(4) C7 0.0187(5) 0.0262(6) 0.0175(5) -0.0010(4) 0.0024(4) -0.0027(4) C8 0.0191(5) 0.0205(5) 0.0219(6) -0.0042(4) 0.0020(4) 0.0014(4) C9 0.0185(5) 0.0164(5) 0.0203(5) -0.0004(4) 0.0002(4) 0.0011(4) _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 1.328(2) . ? N1 N1 1.579(4) 2 ? N1 H3 0.99(3) . ? C1 C1 1.174(5) 2 ? C1 C2 1.424(3) . ? C1 H3 1.01(3) . ? C2 N3 1.323(2) . ? C2 C3 1.428(3) . ? C2 C4 1.4795(15) . ? N3 N3 1.583(4) 2 ? N3 H1 0.95(3) . ? C3 C3 1.157(5) 2 ? C3 H1 0.97(3) . ? C4 C5 1.4014(15) . ? C4 C9 1.4019(15) . ? C5 C6 1.3915(15) . ? C5 H5 0.971(15) . ? C6 C7 1.3923(16) . ? C6 H6 0.973(15) . ? C7 C8 1.3903(16) . ? C7 H7 0.977(16) . ? C8 C9 1.3894(15) . ? C8 H8 0.969(16) . ? C9 H9 0.975(15) . ? 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 N1 113.81(10) . 2 ? C2 N1 H3 127.1(15) . . ? N1 N1 H3 101.8(15) 2 . ? C1 C1 C2 120.20(14) 2 . ? C1 C1 H3 119.8(15) 2 . ? C2 C1 H3 116.9(15) . . ? N3 C2 N1 128.39(15) . . ? N3 C2 C1 119.06(16) . . ? N1 C2 C1 15.25(13) . . ? N3 C2 C3 14.82(14) . . ? N1 C2 C3 118.70(16) . . ? C1 C2 C3 112.64(17) . . ? N3 C2 C4 114.98(12) . . ? N1 C2 C4 116.62(12) . . ? C1 C2 C4 124.45(14) . . ? C3 C2 C4 122.91(13) . . ? C2 N3 N3 113.98(10) . 2 ? C2 N3 H1 130.6(17) . . ? N3 N3 H1 100.6(15) 2 . ? C3 C3 C2 120.64(14) 2 . ? C3 C3 H1 118.0(16) 2 . ? C2 C3 H1 117.8(15) . . ? C5 C4 C9 118.94(10) . . ? C5 C4 C2 121.00(9) . . ? C9 C4 C2 120.05(9) . . ? C6 C5 C4 120.19(10) . . ? C6 C5 H5 119.5(9) . . ? C4 C5 H5 120.3(9) . . ? C5 C6 C7 120.40(10) . . ? C5 C6 H6 118.9(9) . . ? C7 C6 H6 120.7(9) . . ? C8 C7 C6 119.75(10) . . ? C8 C7 H7 119.7(9) . . ? C6 C7 H7 120.5(9) . . ? C9 C8 C7 120.17(10) . . ? C9 C8 H8 118.2(9) . . ? C7 C8 H8 121.7(9) . . ? C8 C9 C4 120.55(10) . . ? C8 C9 H9 120.6(8) . . ? C4 C9 H9 118.9(8) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 29.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.407 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.048 #=========================================================END data_(15) _database_code_CSD 203939 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-bis(5-bromo-2-pyrimidyl)-9,9-dihexylfluorene ; _chemical_name_common 2,7-bis(5-bromo-2-pyrimidyl)-9,9-dihexylfluorene _chemical_melting_point '179.3--179.8 \%C' _chemical_formula_moiety ? _chemical_formula_sum 'C33 H36 Br2 N4' _chemical_formula_weight 648.48 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 10.244(3) _cell_length_b 10.979(3) _cell_length_c 13.520(3) _cell_angle_alpha 93.37(1) _cell_angle_beta 93.99(1) _cell_angle_gamma 95.14(1) _cell_volume 1507.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 654 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 20.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 2.717 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.4361 _exptl_absorpt_correction_T_max 0.7780 _exptl_absorpt_process_details 'XPREP (SHELXTL), R(int)=0.158 before correction' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 0.00 0.0500 1.00 0.00 0.00 0.0500 -1.00 -1.00 0.00 0.1000 1.00 1.00 0.00 0.1000 0.00 1.00 -3.00 0.2000 0.00 -1.00 -3.00 0.2100 0.00 1.00 2.00 0.1800 0.00 0.00 1.00 0.2000 1.00 -1.00 0.00 0.1000 -1.00 1.00 0.00 0.1000 0.00 0.00 -1.00 0.2100 _exptl_special_details ; The data collection nominally covered full sphere of reciprocal Space, by a combination of 5 sets of \w scans each set at different \f and/or 2\q angles and each scan (10 s exposure) covering 0.3\% in \w. Crystal to detector distance 4.51 cm. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 16402 _diffrn_reflns_av_R_equivalents 0.1187 _diffrn_reflns_av_sigmaI/netI 0.1006 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 27.5 _reflns_number_total 6944 _reflns_number_gt 5144 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART-NT V5.0 (Bruker, 1998)' _computing_cell_refinement 'SMART-NT V5.0 (Bruker, 1998)' _computing_data_reduction 'SMART-NT V5.0 (Bruker, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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. ; _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^)+(0.1314P)^2^+10.9455P] 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 6944 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.0941 _refine_ls_wR_factor_ref 0.2780 _refine_ls_wR_factor_gt 0.2573 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 0.68059(9) 0.53389(7) 1.87517(5) 0.0339(3) Uani 1 1 d . . . Br2 Br 0.74665(8) 0.99483(7) 0.56660(5) 0.0312(2) Uani 1 1 d . . . N1 N 0.7351(6) 0.6322(6) 1.5907(5) 0.0291(14) Uani 1 1 d . . . N2 N 0.5063(6) 0.6262(6) 1.6115(5) 0.0249(12) Uani 1 1 d . . . N3 N 0.7666(6) 0.9092(6) 0.8580(5) 0.0265(13) Uani 1 1 d . . . N4 N 0.5407(6) 0.8896(6) 0.8024(4) 0.0242(12) Uani 1 1 d . . . C1 C 0.5385(6) 0.7531(6) 1.2629(5) 0.0173(12) Uani 1 1 d . . . C2 C 0.6691(6) 0.7472(6) 1.3023(5) 0.0173(12) Uani 1 1 d . . . C3 C 0.6938(6) 0.7114(6) 1.3972(5) 0.0204(13) Uani 1 1 d . . . H3 H 0.7814 0.7067 1.4233 0.024 Uiso 1 1 d R . . C4 C 0.5879(7) 0.6819(6) 1.4555(5) 0.0188(13) Uani 1 1 d . . . C5 C 0.4583(6) 0.6898(6) 1.4154(5) 0.0195(13) Uani 1 1 d . . . H5 H 0.3872 0.6705 1.4548 0.023 Uiso 1 1 d R . . C6 C 0.4326(6) 0.7253(6) 1.3199(5) 0.0190(13) Uani 1 1 d . . . H6 H 0.3451 0.7306 1.2939 0.023 Uiso 1 1 d R . . C7 C 0.5434(6) 0.7888(6) 1.1603(4) 0.0147(12) Uani 1 1 d . . . C8 C 0.6755(6) 0.8087(6) 1.1381(5) 0.0170(12) Uani 1 1 d . . . C9 C 0.7069(6) 0.8410(6) 1.0464(5) 0.0162(12) Uani 1 1 d . . . H9 H 0.7962 0.8551 1.0324 0.019 Uiso 1 1 d R . . C10 C 0.6060(6) 0.8532(6) 0.9724(5) 0.0176(12) Uani 1 1 d . . . C11 C 0.4743(6) 0.8356(6) 0.9951(5) 0.0188(12) Uani 1 1 d . . . H11 H 0.4064 0.8460 0.9459 0.023 Uiso 1 1 d R . . C12 C 0.4422(6) 0.8031(6) 1.0881(5) 0.0199(13) Uani 1 1 d . . . H12 H 0.3531 0.7908 1.1028 0.024 Uiso 1 1 d R . . C13 C 0.6117(7) 0.6438(6) 1.5581(5) 0.0206(13) Uani 1 1 d . . . C14 C 0.7555(8) 0.6000(7) 1.6844(6) 0.0314(17) Uani 1 1 d . . . H14 H 0.8422 0.5903 1.7101 0.038 Uiso 1 1 d R . . C15 C 0.6536(8) 0.5807(6) 1.7438(5) 0.0256(15) Uani 1 1 d . . . C16 C 0.5270(8) 0.5955(7) 1.7049(6) 0.0268(15) Uani 1 1 d . . . H16 H 0.4551 0.5836 1.7449 0.032 Uiso 1 1 d R . . C17 C 0.6395(6) 0.8866(6) 0.8725(5) 0.0167(12) Uani 1 1 d . . . C18 C 0.7967(7) 0.9403(7) 0.7689(6) 0.0286(16) Uani 1 1 d . . . H18 H 0.8863 0.9575 0.7568 0.034 Uiso 1 1 d R . . C19 C 0.7020(7) 0.9483(6) 0.6933(5) 0.0240(14) Uani 1 1 d . . . C20 C 0.5729(7) 0.9207(7) 0.7127(6) 0.0278(15) Uani 1 1 d . . . H20 H 0.5056 0.9238 0.6613 0.033 Uiso 1 1 d R . . C21 C 0.7671(6) 0.7886(6) 1.2290(5) 0.0156(12) Uani 1 1 d . . . C22 C 0.8654(7) 0.6936(6) 1.2060(5) 0.0206(13) Uani 1 1 d . . . H22A H 0.9253 0.7273 1.1580 0.027 Uiso 1 1 d R . . H22B H 0.9191 0.6828 1.2678 0.027 Uiso 1 1 d R . . C23 C 0.8039(7) 0.5683(6) 1.1639(5) 0.0227(14) Uani 1 1 d . . . H23A H 0.7487 0.5778 1.1025 0.029 Uiso 1 1 d R . . H23B H 0.7467 0.5318 1.2124 0.029 Uiso 1 1 d R . . C24 C 0.9096(7) 0.4825(6) 1.1408(5) 0.0218(13) Uani 1 1 d . . . H24A H 0.9672 0.5206 1.0934 0.028 Uiso 1 1 d R . . H24B H 0.9642 0.4736 1.2027 0.028 Uiso 1 1 d R . . C25 C 0.8553(7) 0.3565(6) 1.0979(6) 0.0265(15) Uani 1 1 d . . . H25A H 0.8053 0.3644 1.0338 0.035 Uiso 1 1 d R . . H25B H 0.7938 0.3197 1.1434 0.035 Uiso 1 1 d R . . C26 C 0.9629(7) 0.2712(6) 1.0814(6) 0.0282(15) Uani 1 1 d . . . H26A H 1.0239 0.3079 1.0355 0.037 Uiso 1 1 d R . . H26B H 1.0135 0.2642 1.1454 0.037 Uiso 1 1 d R . . C27 C 0.9098(8) 0.1440(7) 1.0391(8) 0.041(2) Uani 1 1 d . . . H27A H 0.9828 0.0938 1.0303 0.06(2) Uiso 1 1 d R . . H27B H 0.8614 0.1499 0.9749 0.06(2) Uiso 1 1 d R . . H27C H 0.8508 0.1063 1.0849 0.06(2) Uiso 1 1 d R . . C28 C 0.8490(6) 0.9107(6) 1.2681(5) 0.0193(13) Uani 1 1 d . . . H28A H 0.9063 0.8942 1.3267 0.025 Uiso 1 1 d R . . H28B H 0.9066 0.9372 1.2162 0.025 Uiso 1 1 d R . . C29 C 0.7691(6) 1.0165(6) 1.2972(5) 0.0197(13) Uani 1 1 d . . . H29A H 0.7162 1.0380 1.2379 0.026 Uiso 1 1 d R . . H29B H 0.7079 0.9897 1.3466 0.026 Uiso 1 1 d R . . C30 C 0.8557(7) 1.1297(6) 1.3404(5) 0.0228(14) Uani 1 1 d . . . H30A H 0.9158 1.1577 1.2906 0.030 Uiso 1 1 d R . . H30B H 0.9097 1.1082 1.3991 0.030 Uiso 1 1 d R . . C31 C 0.7736(7) 1.2338(6) 1.3707(5) 0.0229(14) Uani 1 1 d . . . H31A H 0.7105 1.2035 1.4177 0.030 Uiso 1 1 d R . . H31B H 0.7223 1.2565 1.3111 0.030 Uiso 1 1 d R . . C32 C 0.8543(8) 1.3490(7) 1.4191(6) 0.0307(16) Uani 1 1 d . . . H32A H 0.9211 1.3765 1.3738 0.040 Uiso 1 1 d R . . H32B H 0.7954 1.4148 1.4272 0.040 Uiso 1 1 d R . . C33 C 0.9230(8) 1.3309(7) 1.5194(6) 0.0324(17) Uani 1 1 d . . . H33A H 0.9729 1.4076 1.5453 0.038(15) Uiso 1 1 d R . . H33B H 0.9829 1.2670 1.5120 0.038(15) Uiso 1 1 d R . . H33C H 0.8576 1.3064 1.5655 0.038(15) Uiso 1 1 d 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 0.0480(5) 0.0347(4) 0.0178(4) 0.0040(3) -0.0037(3) 0.0004(3) Br2 0.0379(5) 0.0387(5) 0.0174(4) 0.0018(3) 0.0046(3) 0.0043(3) N1 0.021(3) 0.042(4) 0.025(3) 0.004(3) 0.000(2) 0.005(3) N2 0.026(3) 0.031(3) 0.019(3) 0.002(2) 0.002(2) 0.008(2) N3 0.019(3) 0.037(3) 0.024(3) 0.004(3) 0.002(2) 0.003(2) N4 0.019(3) 0.036(3) 0.018(3) -0.001(2) -0.001(2) 0.006(2) C1 0.017(3) 0.020(3) 0.015(3) -0.003(2) -0.002(2) 0.007(2) C2 0.015(3) 0.021(3) 0.017(3) -0.005(2) 0.004(2) 0.007(2) C3 0.014(3) 0.025(3) 0.022(3) -0.005(3) 0.002(2) 0.006(2) C4 0.022(3) 0.020(3) 0.015(3) -0.004(2) 0.003(2) 0.009(2) C5 0.013(3) 0.024(3) 0.021(3) -0.002(3) -0.001(2) 0.005(2) C6 0.014(3) 0.024(3) 0.020(3) -0.004(2) 0.000(2) 0.010(2) C7 0.014(3) 0.019(3) 0.011(3) -0.006(2) -0.001(2) 0.006(2) C8 0.018(3) 0.019(3) 0.014(3) -0.006(2) -0.001(2) 0.008(2) C9 0.014(3) 0.022(3) 0.013(3) -0.003(2) 0.000(2) 0.007(2) C10 0.018(3) 0.019(3) 0.017(3) -0.003(2) 0.002(2) 0.008(2) C11 0.014(3) 0.025(3) 0.018(3) -0.001(2) 0.000(2) 0.007(2) C12 0.015(3) 0.027(3) 0.018(3) -0.003(3) 0.004(2) 0.004(2) C13 0.024(3) 0.020(3) 0.019(3) -0.003(2) 0.000(3) 0.007(2) C14 0.028(4) 0.038(4) 0.028(4) 0.003(3) -0.006(3) 0.005(3) C15 0.037(4) 0.023(3) 0.015(3) -0.001(3) -0.001(3) -0.002(3) C16 0.030(4) 0.030(4) 0.022(4) 0.002(3) 0.004(3) 0.006(3) C17 0.014(3) 0.020(3) 0.017(3) -0.002(2) -0.002(2) 0.008(2) C18 0.023(4) 0.041(4) 0.020(3) 0.000(3) -0.003(3) -0.002(3) C19 0.028(4) 0.025(3) 0.020(3) -0.001(3) 0.001(3) 0.006(3) C20 0.024(3) 0.038(4) 0.022(4) 0.001(3) -0.006(3) 0.008(3) C21 0.013(3) 0.023(3) 0.012(3) -0.003(2) 0.002(2) 0.008(2) C22 0.023(3) 0.024(3) 0.015(3) -0.006(2) 0.000(2) 0.007(3) C23 0.018(3) 0.024(3) 0.025(3) -0.007(3) -0.004(3) 0.008(3) C24 0.022(3) 0.023(3) 0.021(3) 0.000(3) 0.001(3) 0.011(3) C25 0.026(4) 0.021(3) 0.031(4) -0.003(3) -0.004(3) 0.007(3) C26 0.028(4) 0.023(3) 0.035(4) 0.002(3) 0.007(3) 0.007(3) C27 0.030(4) 0.024(4) 0.069(7) -0.012(4) 0.000(4) 0.009(3) C28 0.017(3) 0.022(3) 0.019(3) -0.004(2) 0.001(2) 0.004(2) C29 0.020(3) 0.027(3) 0.013(3) -0.005(2) 0.002(2) 0.006(2) C30 0.020(3) 0.022(3) 0.025(3) -0.007(3) 0.001(3) 0.002(2) C31 0.023(3) 0.022(3) 0.023(3) -0.003(3) 0.000(3) 0.005(3) C32 0.032(4) 0.024(4) 0.035(4) -0.001(3) 0.003(3) -0.001(3) C33 0.029(4) 0.032(4) 0.034(4) -0.008(3) -0.002(3) 0.000(3) _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 Br1 C15 1.887(7) . ? Br2 C19 1.891(7) . ? N1 C13 1.329(9) . ? N1 C14 1.344(10) . ? N2 C16 1.333(9) . ? N2 C13 1.346(9) . ? N3 C18 1.321(10) . ? N3 C17 1.334(9) . ? N4 C20 1.335(10) . ? N4 C17 1.341(8) . ? C1 C6 1.396(9) . ? C1 C2 1.414(9) . ? C1 C7 1.466(9) . ? C2 C3 1.378(9) . ? C2 C21 1.519(9) . ? C3 C4 1.410(9) . ? C4 C5 1.410(9) . ? C4 C13 1.483(9) . ? C5 C6 1.386(9) . ? C7 C12 1.399(9) . ? C7 C8 1.407(9) . ? C8 C9 1.361(9) . ? C8 C21 1.532(9) . ? C9 C10 1.409(9) . ? C10 C11 1.403(9) . ? C10 C17 1.475(9) . ? C11 C12 1.380(9) . ? C14 C15 1.370(11) . ? C15 C16 1.392(11) . ? C18 C19 1.372(10) . ? C19 C20 1.377(11) . ? C21 C22 1.547(9) . ? C21 C28 1.561(9) . ? C22 C23 1.522(9) . ? C23 C24 1.534(9) . ? C24 C25 1.510(10) . ? C25 C26 1.528(10) . ? C26 C27 1.517(10) . ? C28 C29 1.528(9) . ? C29 C30 1.522(9) . ? C30 C31 1.533(9) . ? C31 C32 1.533(10) . ? C32 C33 1.516(12) . ? 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 C13 N1 C14 117.0(7) . . ? C16 N2 C13 117.6(6) . . ? C18 N3 C17 117.4(6) . . ? C20 N4 C17 117.1(6) . . ? C6 C1 C2 120.8(6) . . ? C6 C1 C7 131.4(6) . . ? C2 C1 C7 107.8(6) . . ? C3 C2 C1 120.3(6) . . ? C3 C2 C21 128.5(6) . . ? C1 C2 C21 111.1(6) . . ? C2 C3 C4 119.6(6) . . ? C5 C4 C3 119.3(6) . . ? C5 C4 C13 120.0(6) . . ? C3 C4 C13 120.7(6) . . ? C6 C5 C4 121.5(6) . . ? C5 C6 C1 118.5(6) . . ? C12 C7 C8 120.1(6) . . ? C12 C7 C1 130.7(6) . . ? C8 C7 C1 109.2(5) . . ? C9 C8 C7 120.8(6) . . ? C9 C8 C21 129.0(6) . . ? C7 C8 C21 110.2(5) . . ? C8 C9 C10 119.6(6) . . ? C11 C10 C9 119.5(6) . . ? C11 C10 C17 120.6(6) . . ? C9 C10 C17 119.8(6) . . ? C12 C11 C10 120.9(6) . . ? C11 C12 C7 118.9(6) . . ? N1 C13 N2 125.3(7) . . ? N1 C13 C4 117.6(6) . . ? N2 C13 C4 117.1(6) . . ? N1 C14 C15 121.4(7) . . ? C14 C15 C16 118.5(7) . . ? C14 C15 Br1 121.8(6) . . ? C16 C15 Br1 119.7(6) . . ? N2 C16 C15 120.3(7) . . ? N3 C17 N4 124.8(6) . . ? N3 C17 C10 117.3(6) . . ? N4 C17 C10 117.9(6) . . ? N3 C18 C19 121.9(7) . . ? C18 C19 C20 117.7(7) . . ? C18 C19 Br2 121.3(6) . . ? C20 C19 Br2 121.0(6) . . ? N4 C20 C19 121.2(7) . . ? C2 C21 C8 101.4(5) . . ? C2 C21 C22 113.5(5) . . ? C8 C21 C22 112.5(5) . . ? C2 C21 C28 111.2(5) . . ? C8 C21 C28 110.8(5) . . ? C22 C21 C28 107.4(5) . . ? C23 C22 C21 115.4(6) . . ? C22 C23 C24 111.2(6) . . ? C25 C24 C23 114.0(6) . . ? C24 C25 C26 112.6(6) . . ? C27 C26 C25 113.2(6) . . ? C29 C28 C21 115.6(5) . . ? C30 C29 C28 112.4(5) . . ? C29 C30 C31 111.5(6) . . ? C30 C31 C32 114.4(6) . . ? C33 C32 C31 114.1(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C27 C26 C25 C24 179.5(7) . . . . ? C26 C25 C24 C23 -176.7(6) . . . . ? C25 C24 C23 C22 -179.5(6) . . . . ? C24 C23 C22 C21 178.3(6) . . . . ? C23 C22 C21 C28 -178.4(6) . . . . ? C22 C21 C28 C29 -178.9(5) . . . . ? C21 C28 C29 C30 176.5(6) . . . . ? C28 C29 C30 C31 -179.0(6) . . . . ? C29 C30 C31 C32 177.5(6) . . . . ? C30 C31 C32 C33 -66.6(9) . . . . ? C9 C10 C17 N3 -2.9(9) . . . . ? C3 C4 C13 N1 -3.7(9) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 4.345 _refine_diff_density_min -1.010 _refine_diff_density_rms 0.219 #====================================================END