# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'dong, huanli' 'Zhao, Guangyao' 'Zhao, Huaping' 'Jiang, Lang' 'Zhang, Xiaotao' 'Tan, Jiahui' 'Meng, Qing' 'Hu, Wenping' _publ_contact_author_name 'Ms huanli dong' _publ_contact_author_email dhl522@iccas.ac.cn _publ_section_title ; Substitution Effect on Molecular Packing and Transistor Performance of Indolo[3,2-b]carbazole Derivatives ; # Attachment '- CHICZ.cif' data_mx4 _database_code_depnum_ccdc_archive 'CCDC 846860' #TrackingRef '- CHICZ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H34 Cl2 N2' _chemical_formula_weight 493.49 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' Cl Cl 0.1484 0.1585 '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)/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 16.759(5) _cell_length_b 4.4914(14) _cell_length_c 18.515(7) _cell_angle_alpha 90.00 _cell_angle_beta 114.283(5) _cell_angle_gamma 90.00 _cell_volume 1270.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3949 _cell_measurement_theta_min 2.2263 _cell_measurement_theta_max 27.4739 _exptl_crystal_description platelet _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.9086 _exptl_absorpt_correction_T_max 0.9843 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13844 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2362 _reflns_number_gt 2197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (Sheldrick, 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. 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^)+(0.0336P)^2^+0.9558P] 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 2362 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.193 _refine_ls_restrained_S_all 1.193 _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 Cl1 Cl 0.59331(4) 0.28906(15) 0.23686(4) 0.0375(2) Uani 1 1 d . . . N1 N 0.86182(12) -0.2783(4) 0.51579(11) 0.0241(4) Uani 1 1 d . . . C2 C 0.75828(15) 0.1787(5) 0.34267(13) 0.0263(5) Uani 1 1 d . . . H2A H 0.7766 0.3114 0.3125 0.032 Uiso 1 1 calc R . . C3 C 0.87659(16) -0.2929(5) 0.79133(13) 0.0286(5) Uani 1 1 d . . . H3A H 0.9297 -0.1677 0.8071 0.034 Uiso 1 1 calc R . . H3B H 0.8255 -0.1582 0.7764 0.034 Uiso 1 1 calc R . . C4 C 0.97642(14) 0.2001(5) 0.43327(13) 0.0240(5) Uani 1 1 d . . . H4A H 0.9611 0.3309 0.3893 0.029 Uiso 1 1 calc R . . C5 C 0.86470(16) -0.2868(5) 0.65012(13) 0.0274(5) Uani 1 1 d . . . H5A H 0.9176 -0.1596 0.6685 0.033 Uiso 1 1 calc R . . H5B H 0.8130 -0.1541 0.6333 0.033 Uiso 1 1 calc R . . C6 C 0.78991(15) -0.1614(5) 0.45366(13) 0.0249(5) Uani 1 1 d . . . C7 C 0.81878(14) 0.0374(5) 0.41002(13) 0.0243(5) Uani 1 1 d . . . C8 C 0.86022(15) -0.4676(5) 0.57878(13) 0.0265(5) Uani 1 1 d . . . H8A H 0.9104 -0.6067 0.5957 0.032 Uiso 1 1 calc R . . H8B H 0.8058 -0.5873 0.5584 0.032 Uiso 1 1 calc R . . C9 C 0.91334(14) 0.0454(5) 0.44923(12) 0.0229(5) Uani 1 1 d . . . C10 C 0.93745(14) -0.1522(5) 0.51493(13) 0.0235(5) Uani 1 1 d . . . C11 C 0.64191(15) -0.0743(6) 0.36488(14) 0.0314(6) Uani 1 1 d . . . H11A H 0.5810 -0.1071 0.3486 0.038 Uiso 1 1 calc R . . C12 C 0.86740(16) -0.4778(5) 0.71915(13) 0.0287(5) Uani 1 1 d . . . H12A H 0.9173 -0.6177 0.7344 0.034 Uiso 1 1 calc R . . H12B H 0.8130 -0.5971 0.7018 0.034 Uiso 1 1 calc R . . C13 C 0.70119(15) -0.2178(5) 0.43139(14) 0.0292(5) Uani 1 1 d . . . H13A H 0.6820 -0.3505 0.4610 0.035 Uiso 1 1 calc R . . C14 C 0.67077(15) 0.1184(5) 0.32144(13) 0.0287(5) Uani 1 1 d . . . C15 C 0.88281(18) -0.4786(6) 0.86183(14) 0.0365(6) Uani 1 1 d . . . H15A H 0.9336 -0.6144 0.8767 0.044 Uiso 1 1 calc R . . H15B H 0.8295 -0.6026 0.8463 0.044 Uiso 1 1 calc R . . C16 C 0.8927(2) -0.2916(7) 0.93370(15) 0.0480(7) Uani 1 1 d . . . H16A H 0.8950 -0.4227 0.9768 0.072 Uiso 1 1 calc R . . H16B H 0.8426 -0.1565 0.9195 0.072 Uiso 1 1 calc R . . H16C H 0.9468 -0.1751 0.9510 0.072 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 Cl1 0.0293(4) 0.0466(4) 0.0280(3) 0.0027(3) 0.0033(3) 0.0021(3) N1 0.0251(10) 0.0275(10) 0.0208(9) 0.0019(8) 0.0105(8) -0.0032(8) C2 0.0286(13) 0.0297(13) 0.0207(11) -0.0020(9) 0.0101(10) -0.0004(10) C3 0.0334(13) 0.0297(13) 0.0245(12) 0.0027(10) 0.0136(11) 0.0021(10) C4 0.0287(12) 0.0255(12) 0.0187(11) 0.0005(9) 0.0108(10) 0.0008(10) C5 0.0330(13) 0.0257(12) 0.0262(12) 0.0010(10) 0.0148(10) -0.0006(10) C6 0.0272(12) 0.0263(12) 0.0215(11) -0.0028(9) 0.0104(10) -0.0025(10) C7 0.0270(12) 0.0268(12) 0.0206(11) -0.0040(9) 0.0111(10) -0.0005(10) C8 0.0293(13) 0.0283(12) 0.0235(12) 0.0026(10) 0.0123(10) -0.0026(10) C9 0.0271(12) 0.0235(11) 0.0168(11) -0.0018(9) 0.0079(9) -0.0002(9) C10 0.0288(12) 0.0239(12) 0.0198(11) -0.0031(9) 0.0122(9) -0.0019(10) C11 0.0232(13) 0.0389(14) 0.0313(13) -0.0052(11) 0.0105(11) -0.0027(11) C12 0.0327(14) 0.0288(13) 0.0264(13) 0.0003(10) 0.0141(11) -0.0019(10) C13 0.0294(13) 0.0325(13) 0.0286(13) -0.0017(10) 0.0149(11) -0.0041(10) C14 0.0281(13) 0.0330(13) 0.0214(11) -0.0019(10) 0.0066(10) 0.0007(10) C15 0.0458(16) 0.0389(15) 0.0263(13) 0.0009(11) 0.0164(12) -0.0044(12) C16 0.065(2) 0.0529(18) 0.0267(14) 0.0017(13) 0.0200(14) -0.0020(15) _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 Cl1 C14 1.747(2) . ? N1 C6 1.382(3) . ? N1 C10 1.394(3) . ? N1 C8 1.452(3) . ? C2 C14 1.380(3) . ? C2 C7 1.395(3) . ? C2 H2A 0.9500 . ? C3 C15 1.516(3) . ? C3 C12 1.526(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C10 1.382(3) 3_756 ? C4 C9 1.395(3) . ? C4 H4A 0.9500 . ? C5 C12 1.524(3) . ? C5 C8 1.526(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C13 1.393(3) . ? C6 C7 1.416(3) . ? C7 C9 1.447(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.423(3) . ? C10 C4 1.382(3) 3_756 ? C11 C13 1.383(3) . ? C11 C14 1.396(3) . ? C11 H11A 0.9500 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9500 . ? C15 C16 1.524(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 C6 N1 C10 108.76(18) . . ? C6 N1 C8 126.36(18) . . ? C10 N1 C8 124.34(19) . . ? C14 C2 C7 117.5(2) . . ? C14 C2 H2A 121.2 . . ? C7 C2 H2A 121.2 . . ? C15 C3 C12 113.6(2) . . ? C15 C3 H3A 108.8 . . ? C12 C3 H3A 108.8 . . ? C15 C3 H3B 108.8 . . ? C12 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C10 C4 C9 116.2(2) 3_756 . ? C10 C4 H4A 121.9 3_756 . ? C9 C4 H4A 121.9 . . ? C12 C5 C8 113.60(19) . . ? C12 C5 H5A 108.8 . . ? C8 C5 H5A 108.8 . . ? C12 C5 H5B 108.8 . . ? C8 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? N1 C6 C13 129.5(2) . . ? N1 C6 C7 109.19(19) . . ? C13 C6 C7 121.3(2) . . ? C2 C7 C6 120.2(2) . . ? C2 C7 C9 132.9(2) . . ? C6 C7 C9 106.86(19) . . ? N1 C8 C5 111.92(19) . . ? N1 C8 H8A 109.2 . . ? C5 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? C5 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C4 C9 C10 121.2(2) . . ? C4 C9 C7 132.5(2) . . ? C10 C9 C7 106.30(19) . . ? C4 C10 N1 128.6(2) 3_756 . ? C4 C10 C9 122.6(2) 3_756 . ? N1 C10 C9 108.86(19) . . ? C13 C11 C14 120.6(2) . . ? C13 C11 H11A 119.7 . . ? C14 C11 H11A 119.7 . . ? C5 C12 C3 112.7(2) . . ? C5 C12 H12A 109.1 . . ? C3 C12 H12A 109.1 . . ? C5 C12 H12B 109.1 . . ? C3 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C11 C13 C6 117.9(2) . . ? C11 C13 H13A 121.1 . . ? C6 C13 H13A 121.1 . . ? C2 C14 C11 122.5(2) . . ? C2 C14 Cl1 118.69(18) . . ? C11 C14 Cl1 118.85(18) . . ? C3 C15 C16 113.1(2) . . ? C3 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? C3 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C10 N1 C6 C13 -179.3(2) . . . . ? C8 N1 C6 C13 -7.5(4) . . . . ? C10 N1 C6 C7 1.7(3) . . . . ? C8 N1 C6 C7 173.5(2) . . . . ? C14 C2 C7 C6 0.5(3) . . . . ? C14 C2 C7 C9 179.9(2) . . . . ? N1 C6 C7 C2 178.2(2) . . . . ? C13 C6 C7 C2 -0.9(3) . . . . ? N1 C6 C7 C9 -1.3(2) . . . . ? C13 C6 C7 C9 179.6(2) . . . . ? C6 N1 C8 C5 -91.0(3) . . . . ? C10 N1 C8 C5 79.6(3) . . . . ? C12 C5 C8 N1 -177.35(19) . . . . ? C10 C4 C9 C10 -0.6(4) 3_756 . . . ? C10 C4 C9 C7 179.7(2) 3_756 . . . ? C2 C7 C9 C4 0.6(4) . . . . ? C6 C7 C9 C4 -179.9(2) . . . . ? C2 C7 C9 C10 -179.1(2) . . . . ? C6 C7 C9 C10 0.4(2) . . . . ? C6 N1 C10 C4 178.8(2) . . . 3_756 ? C8 N1 C10 C4 6.8(4) . . . 3_756 ? C6 N1 C10 C9 -1.5(2) . . . . ? C8 N1 C10 C9 -173.48(19) . . . . ? C4 C9 C10 C4 0.7(4) . . . 3_756 ? C7 C9 C10 C4 -179.6(2) . . . 3_756 ? C4 C9 C10 N1 -179.11(19) . . . . ? C7 C9 C10 N1 0.6(2) . . . . ? C8 C5 C12 C3 177.1(2) . . . . ? C15 C3 C12 C5 -177.9(2) . . . . ? C14 C11 C13 C6 0.6(4) . . . . ? N1 C6 C13 C11 -178.5(2) . . . . ? C7 C6 C13 C11 0.3(3) . . . . ? C7 C2 C14 C11 0.4(4) . . . . ? C7 C2 C14 Cl1 -179.41(17) . . . . ? C13 C11 C14 C2 -0.9(4) . . . . ? C13 C11 C14 Cl1 178.87(19) . . . . ? C12 C3 C15 C16 179.5(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.237 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.048 # Attachment '- ICZ.cif' data_r080402b1 _database_code_depnum_ccdc_archive 'CCDC 846861' #TrackingRef '- ICZ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H12 N2' _chemical_formula_weight 256.30 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 13.125(3) _cell_length_b 5.6381(11) _cell_length_c 8.0541(16) _cell_angle_alpha 90.00 _cell_angle_beta 96.23(3) _cell_angle_gamma 90.00 _cell_volume 592.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9898 _exptl_absorpt_correction_T_max 0.9949 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5613 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1041 _reflns_number_gt 911 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0666P)^2^+0.0546P] 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 1041 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.82415(8) 0.2314(2) 0.47514(13) 0.0214(3) Uani 1 1 d . . . C1 C 0.75524(10) 0.3640(2) 0.37213(15) 0.0202(3) Uani 1 1 d . . . C2 C 0.65402(10) 0.3140(2) 0.31318(16) 0.0237(4) Uani 1 1 d . . . H2 H 0.6223 0.1759 0.3444 0.028 Uiso 1 1 calc R . . C3 C 0.60209(11) 0.4760(2) 0.20693(16) 0.0259(4) Uani 1 1 d . . . H3 H 0.5345 0.4456 0.1653 0.031 Uiso 1 1 calc R . . C4 C 0.64908(11) 0.6851(2) 0.16056(16) 0.0249(4) Uani 1 1 d . . . H4 H 0.6124 0.7911 0.0886 0.030 Uiso 1 1 calc R . . C5 C 0.74993(10) 0.7358(2) 0.22094(15) 0.0211(4) Uani 1 1 d . . . H5 H 0.7807 0.8756 0.1908 0.025 Uiso 1 1 calc R . . C6 C 0.80437(10) 0.5739(2) 0.32734(14) 0.0192(3) Uani 1 1 d . . . C7 C 0.90834(10) 0.5659(2) 0.40842(14) 0.0190(3) Uani 1 1 d . . . C8 C 0.91781(10) 0.3494(2) 0.49965(15) 0.0193(3) Uani 1 1 d . . . C9 C 1.00794(10) 0.2797(2) 0.59188(15) 0.0191(3) Uani 1 1 d . . . H9 H 1.0127 0.1377 0.6510 0.023 Uiso 1 1 calc R . . H1A H 0.8102(11) 0.094(3) 0.5287(19) 0.037(4) 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 N1 0.0240(7) 0.0174(6) 0.0229(6) 0.0038(4) 0.0034(5) -0.0022(4) C1 0.0258(7) 0.0192(7) 0.0161(6) -0.0016(5) 0.0049(5) 0.0017(5) C2 0.0271(8) 0.0218(7) 0.0231(7) -0.0014(5) 0.0061(6) -0.0030(6) C3 0.0243(7) 0.0291(8) 0.0244(7) -0.0037(5) 0.0035(6) 0.0000(6) C4 0.0299(8) 0.0243(7) 0.0203(7) -0.0002(5) 0.0019(6) 0.0055(6) C5 0.0283(8) 0.0176(7) 0.0183(7) -0.0011(5) 0.0064(6) 0.0014(5) C6 0.0246(7) 0.0190(7) 0.0149(6) -0.0034(5) 0.0063(5) 0.0011(5) C7 0.0243(7) 0.0176(7) 0.0158(6) -0.0027(5) 0.0061(5) 0.0016(5) C8 0.0239(7) 0.0182(7) 0.0169(7) -0.0023(5) 0.0067(5) -0.0008(5) C9 0.0261(8) 0.0148(6) 0.0171(7) 0.0000(5) 0.0059(5) 0.0015(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 1.3791(17) . ? N1 C8 1.3929(16) . ? N1 H1A 0.913(17) . ? C1 C2 1.3902(19) . ? C1 C6 1.4133(18) . ? C2 C3 1.3800(19) . ? C2 H2 0.9300 . ? C3 C4 1.3997(19) . ? C3 H3 0.9300 . ? C4 C5 1.3895(19) . ? C4 H4 0.9300 . ? C5 C6 1.3945(18) . ? C5 H5 0.9300 . ? C6 C7 1.4482(18) . ? C7 C9 1.4023(18) 3_766 ? C7 C8 1.4228(17) . ? C8 C9 1.3839(19) . ? C9 C7 1.4023(18) 3_766 ? C9 H9 0.9300 . ? 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 C8 109.72(11) . . ? C1 N1 H1A 126.2(10) . . ? C8 N1 H1A 123.8(9) . . ? N1 C1 C2 129.46(12) . . ? N1 C1 C6 108.65(11) . . ? C2 C1 C6 121.88(12) . . ? C3 C2 C1 117.85(13) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C2 C3 C4 121.36(13) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 120.70(12) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.05(12) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 119.17(12) . . ? C5 C6 C7 133.83(12) . . ? C1 C6 C7 107.00(11) . . ? C9 C7 C8 120.59(12) 3_766 . ? C9 C7 C6 132.84(11) 3_766 . ? C8 C7 C6 106.56(11) . . ? C9 C8 N1 129.06(12) . . ? C9 C8 C7 122.86(12) . . ? N1 C8 C7 108.07(11) . . ? C8 C9 C7 116.55(12) . 3_766 ? C8 C9 H9 121.7 . . ? C7 C9 H9 121.7 3_766 . ? 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 C8 N1 C1 C2 179.14(12) . . . . ? C8 N1 C1 C6 0.09(14) . . . . ? N1 C1 C2 C3 -178.36(12) . . . . ? C6 C1 C2 C3 0.58(18) . . . . ? C1 C2 C3 C4 -0.50(19) . . . . ? C2 C3 C4 C5 -0.13(19) . . . . ? C3 C4 C5 C6 0.69(19) . . . . ? C4 C5 C6 C1 -0.60(17) . . . . ? C4 C5 C6 C7 178.28(12) . . . . ? N1 C1 C6 C5 179.10(10) . . . . ? C2 C1 C6 C5 -0.03(18) . . . . ? N1 C1 C6 C7 -0.06(13) . . . . ? C2 C1 C6 C7 -179.19(11) . . . . ? C5 C6 C7 C9 -0.1(2) . . . 3_766 ? C1 C6 C7 C9 178.87(12) . . . 3_766 ? C5 C6 C7 C8 -178.97(12) . . . . ? C1 C6 C7 C8 0.00(12) . . . . ? C1 N1 C8 C9 -179.15(12) . . . . ? C1 N1 C8 C7 -0.09(13) . . . . ? C9 C7 C8 C9 0.15(19) 3_766 . . . ? C6 C7 C8 C9 179.18(11) . . . . ? C9 C7 C8 N1 -178.98(10) 3_766 . . . ? C6 C7 C8 N1 0.05(13) . . . . ? N1 C8 C9 C7 178.79(11) . . . 3_766 ? C7 C8 C9 C7 -0.14(19) . . . 3_766 ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.170 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.039 # Attachment '- ICZCl.cif' data_r80713i1 _database_code_depnum_ccdc_archive 'CCDC 846862' #TrackingRef '- ICZCl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H10 Cl2 N2' _chemical_formula_weight 325.18 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' Cl Cl 0.1484 0.1585 '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 14.730(3) _cell_length_b 5.8026(12) _cell_length_c 7.6541(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.39(3) _cell_angle_gamma 90.00 _cell_volume 643.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 1967 _cell_measurement_theta_min 2.755 _cell_measurement_theta_max 27.495 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.500 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9243 _exptl_absorpt_correction_T_max 0.9611 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3478 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1126 _reflns_number_gt 1017 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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. 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^)+(0.0476P)^2^+0.4461P] 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 1126 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 Cl1 Cl 0.06445(3) 0.16955(8) 0.69334(6) 0.0202(2) Uani 1 1 d . . . N1 N 0.38538(11) 0.7828(3) 0.77728(19) 0.0133(4) Uani 1 1 d . . . H1 H 0.3938 0.9181 0.7373 0.016 Uiso 1 1 calc R . . C1 C 0.24167(12) 0.2923(3) 0.8161(2) 0.0132(4) Uani 1 1 d . . . H1A H 0.2484 0.1511 0.8744 0.016 Uiso 1 1 calc R . . C2 C 0.15862(13) 0.3565(3) 0.7141(2) 0.0145(4) Uani 1 1 d . . . C3 C 0.14728(13) 0.5669(3) 0.6254(2) 0.0155(4) Uani 1 1 d . . . H3 H 0.0902 0.6051 0.5583 0.019 Uiso 1 1 calc R . . C4 C 0.21984(13) 0.7190(3) 0.6360(2) 0.0151(4) Uani 1 1 d . . . H4 H 0.2127 0.8588 0.5755 0.018 Uiso 1 1 calc R . . C5 C 0.30397(13) 0.6583(3) 0.7392(2) 0.0128(4) Uani 1 1 d . . . C6 C 0.31544(12) 0.4466(3) 0.8287(2) 0.0120(4) Uani 1 1 d . . . C7 C 0.40942(12) 0.4435(3) 0.9251(2) 0.0113(4) Uani 1 1 d . . . C8 C 0.45066(12) 0.6570(3) 0.8889(2) 0.0114(4) Uani 1 1 d . . . C9 C 0.45939(12) 0.2833(3) 1.0380(2) 0.0121(4) Uani 1 1 d . . . H9 H 0.4339 0.1433 1.0634 0.015 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 Cl1 0.0129(3) 0.0189(3) 0.0281(3) 0.00171(18) 0.0013(2) -0.00266(18) N1 0.0158(9) 0.0101(8) 0.0142(8) 0.0038(6) 0.0034(6) -0.0005(6) C1 0.0146(10) 0.0128(9) 0.0131(9) -0.0012(7) 0.0050(7) 0.0011(7) C2 0.0146(10) 0.0140(10) 0.0161(9) -0.0028(7) 0.0055(7) -0.0011(7) C3 0.0140(10) 0.0186(10) 0.0137(9) -0.0017(7) 0.0021(7) 0.0037(8) C4 0.0189(10) 0.0145(9) 0.0125(9) 0.0015(7) 0.0044(7) 0.0039(8) C5 0.0150(10) 0.0139(9) 0.0107(9) -0.0021(7) 0.0053(7) 0.0005(7) C6 0.0146(9) 0.0125(9) 0.0100(8) -0.0015(7) 0.0055(7) 0.0021(7) C7 0.0136(9) 0.0125(9) 0.0089(8) -0.0028(7) 0.0053(7) -0.0001(7) C8 0.0147(10) 0.0116(9) 0.0087(8) -0.0002(6) 0.0041(7) 0.0015(7) C9 0.0159(10) 0.0105(9) 0.0113(9) -0.0002(7) 0.0063(7) -0.0014(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 Cl1 C2 1.7455(19) . ? N1 C8 1.375(2) . ? N1 C5 1.385(2) . ? N1 H1 0.8600 . ? C1 C2 1.378(3) . ? C1 C6 1.398(3) . ? C1 H1A 0.9300 . ? C2 C3 1.392(3) . ? C3 C4 1.377(3) . ? C3 H3 0.9300 . ? C4 C5 1.389(3) . ? C4 H4 0.9300 . ? C5 C6 1.402(2) . ? C6 C7 1.446(3) . ? C7 C9 1.387(2) . ? C7 C8 1.429(2) . ? C8 C9 1.386(3) 3_667 ? C9 C8 1.386(3) 3_667 ? C9 H9 0.9300 . ? 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 C8 N1 C5 109.61(15) . . ? C8 N1 H1 125.2 . . ? C5 N1 H1 125.2 . . ? C2 C1 C6 117.74(17) . . ? C2 C1 H1A 121.1 . . ? C6 C1 H1A 121.1 . . ? C1 C2 C3 121.96(18) . . ? C1 C2 Cl1 119.54(15) . . ? C3 C2 Cl1 118.50(15) . . ? C4 C3 C2 120.64(17) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 118.31(18) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C4 129.58(17) . . ? N1 C5 C6 109.31(16) . . ? C4 C5 C6 121.09(17) . . ? C1 C6 C5 120.25(17) . . ? C1 C6 C7 133.47(16) . . ? C5 C6 C7 106.26(16) . . ? C9 C7 C8 120.36(17) . . ? C9 C7 C6 132.67(17) . . ? C8 C7 C6 106.96(15) . . ? N1 C8 C9 128.92(17) . 3_667 ? N1 C8 C7 107.87(16) . . ? C9 C8 C7 123.19(17) 3_667 . ? C8 C9 C7 116.45(17) 3_667 . ? C8 C9 H9 121.8 3_667 . ? C7 C9 H9 121.8 . . ? 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 C6 C1 C2 C3 0.2(3) . . . . ? C6 C1 C2 Cl1 179.75(12) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? Cl1 C2 C3 C4 -179.20(14) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C8 N1 C5 C4 178.53(17) . . . . ? C8 N1 C5 C6 0.50(19) . . . . ? C3 C4 C5 N1 -176.99(16) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? C2 C1 C6 C7 177.58(17) . . . . ? N1 C5 C6 C1 177.92(15) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? N1 C5 C6 C7 -0.40(18) . . . . ? C4 C5 C6 C7 -178.63(16) . . . . ? C1 C6 C7 C9 0.7(3) . . . . ? C5 C6 C7 C9 178.73(17) . . . . ? C1 C6 C7 C8 -177.84(18) . . . . ? C5 C6 C7 C8 0.16(18) . . . . ? C5 N1 C8 C9 -178.95(17) . . . 3_667 ? C5 N1 C8 C7 -0.39(19) . . . . ? C9 C7 C8 N1 -178.65(15) . . . . ? C6 C7 C8 N1 0.14(18) . . . . ? C9 C7 C8 C9 0.0(3) . . . 3_667 ? C6 C7 C8 C9 178.79(16) . . . 3_667 ? C8 C7 C9 C8 0.0(3) . . . 3_667 ? C6 C7 C9 C8 -178.43(17) . . . 3_667 ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.269 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.054