# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Yoshiro Yamashita' _publ_contact_author_email yoshiro@echem.titech.ac.jp _publ_contact_author_address ; Department of Electronic Chemistry Interdisciplinary Graduate School of Science and Engineering Tokyo Institute of Technology Nagatsuta, Midori-ku, Yokohama 226-8502, Japan ; _publ_contact_author_phone +81-45-924-5571 _publ_contact_author_fax +81-45-924-5489 _publ_section_title ; Preparation, physical properties and n-type FET characteristics of substituted diindenopyrazinediones and bis(dicyanomethylene) derivatives ; loop_ _publ_author_name J.-i.Nishida H.Deno S.Ichimura T.Nakagawa Y.Yamashita # Attachment '- CIFcomp2c2d.cif' #TrackingRef '- CIFcomp2c2d.cif' #============================================================================== data_comp2c _database_code_depnum_ccdc_archive 'CCDC 846545' #TrackingRef '- CIFcomp2c2d.cif' _audit_creation_date 2011-09-29 _audit_creation_method 'by CrystalStructure 3.8' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H6 Cl2 N2 O2' _chemical_formula_moiety 'C18 H6 Cl2 N2 O2' _chemical_formula_weight 353.16 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 6.732(10) _cell_length_b 7.648(13) _cell_length_c 13.372(19) _cell_angle_alpha 90.0000 _cell_angle_beta 94.23(6) _cell_angle_gamma 90.0000 _cell_volume 686.6(18) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5776 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.54 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356.00 _exptl_absorpt_coefficient_mu 0.486 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.509 _exptl_absorpt_correction_T_max 0.953 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 6347 _diffrn_reflns_av_R_equivalents 0.0761 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1560 _reflns_number_gt 1316 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1448 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 1560 _refine_ls_number_parameters 109 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0605P)^2^+1.0241P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.690 _refine_diff_density_min -0.350 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.1484 0.1585 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 -0.40674(9) 0.04039(9) 0.85944(5) 0.0214(3) Uani 1.0 4 d . . . O1 O 0.2915(3) 0.3886(3) 0.74198(14) 0.0224(5) Uani 1.0 4 d . . . N1 N 0.5780(4) 0.5418(3) 0.90404(16) 0.0180(5) Uani 1.0 4 d . . . C1 C -0.0606(4) 0.2104(4) 0.84122(18) 0.0188(6) Uani 1.0 4 d . . . C2 C -0.1937(4) 0.1482(4) 0.90804(19) 0.0187(6) Uani 1.0 4 d . . . C3 C -0.1619(4) 0.1687(4) 1.01134(19) 0.0188(6) Uani 1.0 4 d . . . C4 C 0.0099(4) 0.2529(4) 1.05250(19) 0.0188(6) Uani 1.0 4 d . . . C5 C 0.1446(4) 0.3152(4) 0.98751(19) 0.0179(6) Uani 1.0 4 d . . . C6 C 0.1082(4) 0.2946(4) 0.88318(19) 0.0186(6) Uani 1.0 4 d . . . C7 C 0.2730(4) 0.3786(4) 0.83122(19) 0.0177(6) Uani 1.0 4 d . . . C8 C 0.4110(4) 0.4523(4) 0.91490(19) 0.0176(6) Uani 1.0 4 d . . . C9 C 0.3338(4) 0.4115(4) 1.00695(19) 0.0171(6) Uani 1.0 4 d . . . H1 H -0.0842 0.1959 0.7708 0.0226 Uiso 1.0 4 calc R . . H3 H -0.2571 0.1255 1.0541 0.0225 Uiso 1.0 4 calc R . . H4 H 0.0334 0.2668 1.1230 0.0225 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0177(4) 0.0244(4) 0.0217(4) -0.0036(3) -0.0023(3) -0.0012(3) O1 0.0209(10) 0.0300(12) 0.0161(9) -0.0006(9) 0.0003(8) -0.0004(8) N1 0.0194(11) 0.0187(12) 0.0157(11) 0.0012(9) -0.0002(9) 0.0003(8) C1 0.0206(13) 0.0188(14) 0.0167(12) 0.0032(11) -0.0005(10) -0.0010(10) C2 0.0172(12) 0.0168(13) 0.0216(13) 0.0009(11) -0.0021(11) -0.0003(10) C3 0.0189(13) 0.0191(14) 0.0185(12) 0.0010(11) 0.0027(10) 0.0013(10) C4 0.0211(13) 0.0177(14) 0.0172(12) 0.0021(11) -0.0003(10) 0.0006(10) C5 0.0179(13) 0.0168(13) 0.0186(12) 0.0018(11) -0.0015(10) -0.0015(10) C6 0.0174(13) 0.0193(14) 0.0191(13) 0.0022(11) 0.0012(10) 0.0004(10) C7 0.0171(13) 0.0187(13) 0.0169(12) 0.0010(11) -0.0017(10) -0.0013(10) C8 0.0207(13) 0.0178(14) 0.0138(12) 0.0036(11) -0.0016(10) -0.0001(9) C9 0.0161(13) 0.0168(14) 0.0181(13) 0.0011(11) -0.0000(10) 0.0008(10) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl1 C2 1.739(4) yes . . O1 C7 1.211(4) yes . . N1 C8 1.334(4) yes . . N1 C9 1.339(4) yes . 3_667 C1 C2 1.395(4) yes . . C1 C6 1.388(4) yes . . C2 C3 1.391(4) yes . . C3 C4 1.400(4) yes . . C4 C5 1.386(4) yes . . C5 C6 1.407(4) yes . . C5 C9 1.478(4) yes . . C6 C7 1.497(4) yes . . C7 C8 1.510(4) yes . . C8 C9 1.406(4) yes . . C1 H1 0.950 no . . C3 H3 0.950 no . . C4 H4 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C8 N1 C9 111.2(3) yes . . 3_667 C2 C1 C6 116.4(3) yes . . . Cl1 C2 C1 118.3(2) yes . . . Cl1 C2 C3 119.1(3) yes . . . C1 C2 C3 122.6(3) yes . . . C2 C3 C4 120.3(3) yes . . . C3 C4 C5 118.1(3) yes . . . C4 C5 C6 120.6(3) yes . . . C4 C5 C9 131.0(3) yes . . . C6 C5 C9 108.4(3) yes . . . C1 C6 C5 122.0(3) yes . . . C1 C6 C7 128.6(3) yes . . . C5 C6 C7 109.3(3) yes . . . O1 C7 C6 128.2(3) yes . . . O1 C7 C8 127.2(3) yes . . . C6 C7 C8 104.6(3) yes . . . N1 C8 C7 126.1(3) yes . . . N1 C8 C9 125.3(3) yes . . . C7 C8 C9 108.6(3) yes . . . N1 C9 C5 127.5(3) yes 3_667 . . N1 C9 C8 123.4(3) yes 3_667 . . C5 C9 C8 109.0(3) yes . . . C2 C1 H1 121.800 no . . . C6 C1 H1 121.804 no . . . C2 C3 H3 119.859 no . . . C4 C3 H3 119.865 no . . . C3 C4 H4 120.939 no . . . C5 C4 H4 120.941 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C8 N1 C9 C5 178.4(3) no . . 3_667 3_667 C8 N1 C9 C8 -0.3(4) no . . 3_667 3_667 C9 N1 C8 C7 -179.9(3) no 3_667 . . . C9 N1 C8 C9 0.3(4) no 3_667 . . . C2 C1 C6 C5 0.5(4) no . . . . C2 C1 C6 C7 -178.1(3) no . . . . C6 C1 C2 Cl1 -179.6(2) no . . . . C6 C1 C2 C3 0.2(4) no . . . . Cl1 C2 C3 C4 179.08(18) no . . . . C1 C2 C3 C4 -0.7(5) no . . . . C2 C3 C4 C5 0.4(4) no . . . . C3 C4 C5 C6 0.3(4) no . . . . C3 C4 C5 C9 178.4(3) no . . . . C4 C5 C6 C1 -0.7(4) no . . . . C4 C5 C6 C7 178.1(3) no . . . . C4 C5 C9 N1 1.6(5) no . . . 3_667 C4 C5 C9 C8 -177.3(3) no . . . . C6 C5 C9 N1 179.9(3) no . . . 3_667 C6 C5 C9 C8 1.0(3) no . . . . C9 C5 C6 C1 -179.3(3) no . . . . C9 C5 C6 C7 -0.4(3) no . . . . C1 C6 C7 O1 -0.4(5) no . . . . C1 C6 C7 C8 178.5(3) no . . . . C5 C6 C7 O1 -179.2(3) no . . . . C5 C6 C7 C8 -0.3(3) no . . . . O1 C7 C8 N1 0.0(5) no . . . . O1 C7 C8 C9 179.8(3) no . . . . C6 C7 C8 N1 -178.9(3) no . . . . C6 C7 C8 C9 0.9(3) no . . . . N1 C8 C9 N1 -0.4(5) no . . . 3_667 N1 C8 C9 C5 178.6(3) no . . . . C7 C8 C9 N1 179.8(3) no . . . 3_667 C7 C8 C9 C5 -1.2(3) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N1 3.029(5) no . . O1 C1 3.115(5) no . . O1 C5 3.543(6) no . . O1 C9 3.538(6) no . . N1 N1 2.915(5) no . 3_667 N1 C4 3.203(5) no . 3_667 C1 C4 2.849(6) no . . C2 C5 2.755(5) no . . C3 C6 2.762(5) no . . C8 C8 2.597(5) no . 3_667 C9 C9 2.633(5) no . 3_667 Cl1 O1 3.062(4) no . 2_446 Cl1 C7 3.371(5) no . 1_455 Cl1 C8 3.481(6) no . 1_455 O1 Cl1 3.062(4) no . 2_456 O1 C1 3.297(5) no . 2_556 O1 C3 3.154(6) no . 4_554 O1 C4 3.210(5) no . 4_554 N1 C1 3.518(6) no . 2_556 N1 C2 3.378(6) no . 1_655 N1 C3 3.591(6) no . 1_655 C1 O1 3.297(5) no . 2_546 C1 N1 3.518(6) no . 2_546 C2 N1 3.378(6) no . 1_455 C2 C3 3.520(6) no . 3_557 C2 C4 3.335(6) no . 3_557 C2 C8 3.541(6) no . 1_455 C3 O1 3.154(6) no . 4_455 C3 N1 3.591(6) no . 1_455 C3 C2 3.520(6) no . 3_557 C3 C3 3.406(6) no . 3_557 C3 C4 3.507(7) no . 3_557 C3 C8 3.525(6) no . 3_567 C3 C9 3.415(7) no . 3_567 C4 O1 3.210(5) no . 4_455 C4 C2 3.335(6) no . 3_557 C4 C3 3.507(7) no . 3_557 C4 C5 3.492(7) no . 3_567 C4 C9 3.508(6) no . 3_567 C5 C4 3.492(7) no . 3_567 C5 C5 3.462(6) no . 3_567 C7 Cl1 3.371(5) no . 1_655 C8 Cl1 3.481(6) no . 1_655 C8 C2 3.541(6) no . 1_655 C8 C3 3.525(6) no . 3_567 C9 C3 3.415(7) no . 3_567 C9 C4 3.508(6) no . 3_567 Cl1 H1 2.8133 no . . Cl1 H3 2.7981 no . . O1 H1 2.9769 no . . N1 H4 3.0418 no . 3_667 C1 H3 3.2917 no . . C2 H4 3.2821 no . . C3 H1 3.3033 no . . C5 H1 3.3085 no . . C5 H3 3.2514 no . . C6 H4 3.2891 no . . C7 H1 2.8463 no . . C9 H4 2.8607 no . . H3 H4 2.3617 no . . Cl1 H1 3.1564 no . 2_446 Cl1 H3 2.9070 no . 3_457 Cl1 H4 3.4358 no . 3_557 Cl1 H4 3.4852 no . 4_454 O1 H1 3.0794 no . 2_556 O1 H3 2.5113 no . 4_554 O1 H4 2.6424 no . 4_554 N1 H1 2.6210 no . 2_556 N1 H3 3.4107 no . 3_567 C1 H3 3.5623 no . 3_557 C2 H4 3.3881 no . 3_557 C5 H3 3.5080 no . 3_557 C6 H3 3.4504 no . 3_557 C6 H4 3.4862 no . 3_567 C7 H1 3.5438 no . 2_556 C7 H4 3.4887 no . 3_567 C7 H4 3.5758 no . 4_554 C8 H1 3.3797 no . 2_556 C8 H3 3.4255 no . 3_567 C9 H3 3.5370 no . 1_655 H1 Cl1 3.1564 no . 2_456 H1 O1 3.0794 no . 2_546 H1 N1 2.6210 no . 2_546 H1 C7 3.5438 no . 2_546 H1 C8 3.3797 no . 2_546 H1 H4 3.1408 no . 4_454 H3 Cl1 2.9070 no . 3_457 H3 O1 2.5113 no . 4_455 H3 N1 3.4107 no . 3_567 H3 C1 3.5623 no . 3_557 H3 C5 3.5080 no . 3_557 H3 C6 3.4504 no . 3_557 H3 C8 3.4255 no . 3_567 H3 C9 3.5370 no . 1_455 H4 Cl1 3.4358 no . 3_557 H4 Cl1 3.4852 no . 4_555 H4 O1 2.6424 no . 4_455 H4 C2 3.3881 no . 3_557 H4 C6 3.4862 no . 3_567 H4 C7 3.4887 no . 3_567 H4 C7 3.5758 no . 4_455 H4 H1 3.1408 no . 4_555 #============================================================================== #============================================================================== data_comp2d _database_code_depnum_ccdc_archive 'CCDC 846546' #TrackingRef '- CIFcomp2c2d.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H6 Br2 N2 O2' _chemical_formula_moiety 'C18 H6 Br2 N2 O2' _chemical_formula_weight 442.07 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 6.838(9) _cell_length_b 7.760(10) _cell_length_c 13.380(13) _cell_angle_alpha 90.0000 _cell_angle_beta 92.92(5) _cell_angle_gamma 90.0000 _cell_volume 709.1(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5230 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 93 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 2.070 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428.00 _exptl_absorpt_coefficient_mu 5.747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.301 _exptl_absorpt_correction_T_max 0.750 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 93 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.667 _diffrn_reflns_number 6693 _diffrn_reflns_av_R_equivalents 0.0877 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1624 _reflns_number_gt 1113 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0650 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 1624 _refine_ls_number_parameters 109 _refine_ls_goodness_of_fit_ref 0.873 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.760 _refine_diff_density_min -0.700 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Br Br -0.2901 2.4595 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 -0.40959(6) 0.04379(6) 0.85761(3) 0.01586(12) Uani 1.0 4 d . . . O1 O 0.2921(4) 0.4053(4) 0.74317(18) 0.0179(7) Uani 1.0 4 d . . . N1 N 0.4239(5) 0.4553(5) 1.0965(2) 0.0127(7) Uani 1.0 4 d . . . C1 C -0.0501(6) 0.2214(5) 0.8434(3) 0.0131(9) Uani 1.0 4 d . . . C2 C -0.1809(6) 0.1569(6) 0.9101(3) 0.0136(9) Uani 1.0 4 d . . . C3 C -0.1503(6) 0.1736(5) 1.0133(3) 0.0146(9) Uani 1.0 4 d . . . C4 C 0.0184(6) 0.2542(5) 1.0542(3) 0.0143(9) Uani 1.0 4 d . . . C5 C 0.1495(6) 0.3190(5) 0.9889(3) 0.0116(9) Uani 1.0 4 d . . . C6 C 0.1162(6) 0.3025(5) 0.8845(3) 0.0128(9) Uani 1.0 4 d . . . C7 C 0.2747(6) 0.3885(6) 0.8326(3) 0.0147(9) Uani 1.0 4 d . . . C8 C 0.4129(6) 0.4580(6) 0.9155(3) 0.0136(8) Uani 1.0 4 d . . . C9 C 0.3348(6) 0.4129(5) 1.0073(3) 0.0144(9) Uani 1.0 4 d . . . H1 H -0.0733 0.2105 0.7731 0.0157 Uiso 1.0 4 calc R . . H3 H -0.2448 0.1298 1.0563 0.0175 Uiso 1.0 4 calc R . . H4 H 0.0418 0.2641 1.1245 0.0171 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.01035(18) 0.0201(3) 0.0170(2) -0.0028(3) -0.00045(12) -0.00108(19) O1 0.0132(16) 0.0278(19) 0.0127(14) -0.0026(13) 0.0020(11) 0.0008(11) N1 0.0108(16) 0.0146(18) 0.0126(15) 0.0003(16) -0.0011(11) -0.0006(14) C1 0.011(3) 0.015(3) 0.0130(19) -0.0002(18) 0.0015(15) 0.0030(16) C2 0.010(2) 0.013(3) 0.017(2) 0.0010(18) -0.0031(15) -0.0021(16) C3 0.011(3) 0.014(3) 0.019(2) 0.0032(18) 0.0051(16) 0.0024(16) C4 0.016(3) 0.016(3) 0.0109(19) 0.0025(18) 0.0009(15) -0.0003(16) C5 0.009(2) 0.013(3) 0.013(2) 0.0010(18) 0.0009(15) 0.0021(15) C6 0.011(3) 0.015(3) 0.012(2) 0.0029(17) 0.0005(15) 0.0018(15) C7 0.008(2) 0.016(3) 0.020(3) 0.0025(17) 0.0006(15) 0.0005(16) C8 0.0106(19) 0.015(2) 0.0152(19) 0.001(2) 0.0023(14) -0.0013(17) C9 0.009(2) 0.012(3) 0.022(2) 0.0020(17) 0.0021(15) -0.0001(16) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Br1 C2 1.897(5) yes . . O1 C7 1.215(5) yes . . N1 C8 1.320(5) yes . 3_667 N1 C9 1.353(5) yes . . C1 C2 1.388(6) yes . . C1 C6 1.389(6) yes . . C2 C3 1.392(5) yes . . C3 C4 1.399(6) yes . . C4 C5 1.378(6) yes . . C5 C6 1.409(5) yes . . C5 C9 1.471(6) yes . . C6 C7 1.477(6) yes . . C7 C8 1.520(6) yes . . C8 C9 1.408(6) yes . . C1 H1 0.950 no . . C3 H3 0.950 no . . C4 H4 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C8 N1 C9 111.2(3) yes 3_667 . . C2 C1 C6 116.7(4) yes . . . Br1 C2 C1 118.3(3) yes . . . Br1 C2 C3 119.3(3) yes . . . C1 C2 C3 122.4(4) yes . . . C2 C3 C4 120.5(4) yes . . . C3 C4 C5 117.8(4) yes . . . C4 C5 C6 121.1(4) yes . . . C4 C5 C9 131.1(4) yes . . . C6 C5 C9 107.8(4) yes . . . C1 C6 C5 121.4(4) yes . . . C1 C6 C7 128.6(4) yes . . . C5 C6 C7 109.9(4) yes . . . O1 C7 C6 128.6(4) yes . . . O1 C7 C8 126.3(4) yes . . . C6 C7 C8 105.1(3) yes . . . N1 C8 C7 126.2(3) yes 3_667 . . N1 C8 C9 126.4(4) yes 3_667 . . C7 C8 C9 107.4(4) yes . . . N1 C9 C5 127.8(4) yes . . . N1 C9 C8 122.4(4) yes . . . C5 C9 C8 109.8(3) yes . . . C2 C1 H1 121.633 no . . . C6 C1 H1 121.636 no . . . C2 C3 H3 119.729 no . . . C4 C3 H3 119.733 no . . . C3 C4 H4 121.125 no . . . C5 C4 H4 121.120 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C8 N1 C9 C5 -179.0(4) no 3_667 . . . C8 N1 C9 C8 0.3(5) no 3_667 . . . C9 N1 C8 C7 179.8(4) no . . 3_667 3_667 C9 N1 C8 C9 -0.3(6) no . . 3_667 3_667 C2 C1 C6 C5 -0.3(6) no . . . . C2 C1 C6 C7 -177.3(4) no . . . . C6 C1 C2 Br1 -179.6(3) no . . . . C6 C1 C2 C3 0.8(6) no . . . . Br1 C2 C3 C4 179.1(3) no . . . . C1 C2 C3 C4 -1.3(6) no . . . . C2 C3 C4 C5 1.3(6) no . . . . C3 C4 C5 C6 -0.9(6) no . . . . C3 C4 C5 C9 178.3(4) no . . . . C4 C5 C6 C1 0.4(6) no . . . . C4 C5 C6 C7 177.8(4) no . . . . C4 C5 C9 N1 1.6(7) no . . . . C4 C5 C9 C8 -177.8(4) no . . . . C6 C5 C9 N1 -179.1(4) no . . . . C6 C5 C9 C8 1.5(4) no . . . . C9 C5 C6 C1 -179.0(3) no . . . . C9 C5 C6 C7 -1.5(4) no . . . . C1 C6 C7 O1 -0.3(7) no . . . . C1 C6 C7 C8 178.2(4) no . . . . C5 C6 C7 O1 -177.5(4) no . . . . C5 C6 C7 C8 1.0(4) no . . . . O1 C7 C8 N1 -1.5(7) no . . . 3_667 O1 C7 C8 C9 178.5(4) no . . . . C6 C7 C8 N1 180.0(4) no . . . 3_667 C6 C7 C8 C9 -0.1(4) no . . . . N1 C8 C9 N1 -0.3(7) no 3_667 . . . N1 C8 C9 C5 179.1(4) no 3_667 . . . C7 C8 C9 N1 179.7(3) no . . . . C7 C8 C9 C5 -0.9(4) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N1 3.020(5) no . 3_667 O1 C1 3.104(6) no . . O1 C5 3.540(6) no . . O1 C9 3.532(6) no . . N1 N1 2.917(5) no . 3_667 N1 C4 3.207(6) no . . C1 C4 2.846(6) no . . C2 C5 2.749(6) no . . C3 C6 2.759(6) no . . C8 C8 2.585(5) no . 3_667 C9 C9 2.648(6) no . 3_667 Br1 O1 3.075(4) no . 2_446 Br1 C7 3.443(5) no . 1_455 Br1 C8 3.535(6) no . 1_455 O1 Br1 3.075(4) no . 2_456 O1 C1 3.268(6) no . 2_556 O1 C3 3.180(6) no . 4_554 O1 C4 3.274(6) no . 4_554 O1 C6 3.595(6) no . 2_556 N1 C1 3.573(6) no . 4_555 N1 C2 3.436(7) no . 3_567 C1 O1 3.268(6) no . 2_546 C1 N1 3.573(6) no . 4_454 C2 N1 3.436(7) no . 3_567 C2 C3 3.539(7) no . 3_557 C2 C4 3.404(7) no . 3_557 C3 O1 3.180(6) no . 4_455 C3 C2 3.539(7) no . 3_557 C3 C3 3.419(7) no . 3_557 C3 C4 3.569(7) no . 3_557 C3 C8 3.533(7) no . 3_567 C3 C9 3.454(7) no . 3_567 C4 O1 3.274(6) no . 4_455 C4 C2 3.404(7) no . 3_557 C4 C3 3.569(7) no . 3_557 C4 C5 3.542(7) no . 3_567 C5 C4 3.542(7) no . 3_567 C5 C5 3.496(7) no . 3_567 C6 O1 3.595(6) no . 2_546 C7 Br1 3.443(5) no . 1_655 C8 Br1 3.535(6) no . 1_655 C8 C3 3.533(7) no . 3_567 C9 C3 3.454(7) no . 3_567 Br1 H1 2.9164 no . . Br1 H3 2.9121 no . . O1 H1 2.9653 no . . N1 H4 3.0445 no . . C1 H3 3.2835 no . . C2 H4 3.2855 no . . C3 H1 3.2959 no . . C5 H1 3.3045 no . . C5 H3 3.2392 no . . C6 H4 3.2904 no . . C7 H1 2.8305 no . . C9 H4 2.8515 no . . H3 H4 2.3616 no . . Br1 H1 3.1210 no . 2_446 Br1 H3 3.0001 no . 3_457 Br1 H4 3.4682 no . 3_557 Br1 H4 3.4573 no . 4_454 O1 H1 3.0649 no . 2_556 O1 H3 2.5143 no . 4_554 O1 H4 2.7270 no . 4_554 N1 H1 2.6893 no . 4_555 N1 H3 3.4534 no . 1_655 C2 H4 3.4406 no . 3_557 C6 H3 3.5472 no . 3_557 C6 H4 3.5331 no . 3_567 C7 H1 3.5641 no . 2_556 C7 H4 3.5226 no . 3_567 C8 H1 3.4191 no . 2_556 C8 H3 3.4265 no . 3_567 H1 Br1 3.1210 no . 2_456 H1 O1 3.0649 no . 2_546 H1 N1 2.6893 no . 4_454 H1 C7 3.5641 no . 2_546 H1 C8 3.4191 no . 2_546 H1 H4 3.2225 no . 4_454 H3 Br1 3.0001 no . 3_457 H3 O1 2.5143 no . 4_455 H3 N1 3.4534 no . 1_455 H3 C6 3.5472 no . 3_557 H3 C8 3.4265 no . 3_567 H4 Br1 3.4682 no . 3_557 H4 Br1 3.4573 no . 4_555 H4 O1 2.7270 no . 4_455 H4 C2 3.4406 no . 3_557 H4 C6 3.5331 no . 3_567 H4 C7 3.5226 no . 3_567 H4 H1 3.2225 no . 4_555 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================