# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Sachio Horiuchi' _publ_contact_author_email S-HORIUCHI@AIST.GO.JP _publ_section_title ; Proton-Displacive Ferroelectricity in Neutral Cocrystals of Anilic Acids with Phenazine ; loop_ _publ_author_name 'Sachio Horiuchi' 'Reiji Kumai' 'Yoshinori Tokura' # Attachment 'PhzXA-rev.cif' data__Phz-H2fa(alpha-form) _database_code_depnum_ccdc_archive 'CCDC 716153' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H10 F2 N2 O4 ' _chemical_formula_moiety 'C18 H10 F2 N2 O4 ' _chemical_formula_weight 356.28 _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 12.318(3) _cell_length_b 3.8374(9) _cell_length_c 16.385(4) _cell_angle_alpha 90.0000 _cell_angle_beta 104.675(2) _cell_angle_gamma 90.0000 _cell_volume 749.3(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3051 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 293.1 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour darkbrown _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.579 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364.00 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.904 _exptl_absorpt_correction_T_max 0.982 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 6406 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.913 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1550 _reflns_number_gt 1183 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0525 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1193 _refine_ls_number_parameters 139 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0017Fo^2^ + 1.0000\s(Fo^2^)]' _refine_ls_shift/su_max 0.1475 _refine_diff_density_max 0.17 _refine_diff_density_min -0.16 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 28(34) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; 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 F(1) F 0.10965(8) -0.2742(3) 0.15438(7) 0.0518(3) Uani 1.00 1 d . . . O(1) O 0.22935(10) 0.0610(3) 0.05997(8) 0.0480(3) Uani 1.00 1 d . . . O(2) O 0.11571(10) 0.3402(3) -0.09119(8) 0.0472(3) Uani 1.00 1 d . . . N(1) N 0.39486(10) 0.3758(3) 0.00688(8) 0.0305(3) Uani 1.00 1 d . . . C(1) C 0.05918(13) -0.1361(4) 0.07906(10) 0.0343(4) Uani 1.00 1 d . . . C(2) C 0.11975(12) 0.0295(4) 0.03312(10) 0.0335(4) Uani 1.00 1 d . . . C(3) C 0.06107(13) 0.1816(3) -0.05073(10) 0.0325(4) Uani 1.00 1 d . . . C(4) C 0.46585(12) 0.5360(3) 0.07213(10) 0.0289(3) Uani 1.00 1 d . . . C(5) C 0.57262(12) 0.6623(3) 0.06517(9) 0.0288(3) Uani 1.00 1 d . . . C(6) C 0.64459(14) 0.8315(4) 0.13540(10) 0.0354(4) Uani 1.00 1 d . . . C(7) C 0.61215(15) 0.8673(4) 0.20860(11) 0.0392(4) Uani 1.00 1 d . . . C(8) C 0.50685(14) 0.7409(4) 0.21546(11) 0.0400(4) Uani 1.00 1 d . . . C(9) C 0.43508(14) 0.5811(4) 0.14960(10) 0.0354(4) Uani 1.00 1 d . . . H(1) H 0.268(3) 0.195(6) 0.024(2) 0.111(11) Uiso 1.00 1 d . . . H(2) H 0.7202(16) 0.906(4) 0.1298(12) 0.043(4) Uiso 1.00 1 d . . . H(3) H 0.6638(14) 0.983(4) 0.2565(12) 0.040(4) Uiso 1.00 1 d . . . H(4) H 0.4894(18) 0.771(4) 0.2715(13) 0.050(5) Uiso 1.00 1 d . . . H(5) H 0.3628(17) 0.496(4) 0.1525(13) 0.046(5) Uiso 1.00 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0379(5) 0.0754(8) 0.0398(5) -0.0023(4) 0.0055(4) 0.0200(4) O(1) 0.0247(6) 0.0689(9) 0.0485(7) -0.0074(5) 0.0059(5) 0.0148(6) O(2) 0.0352(6) 0.0636(8) 0.0469(7) -0.0048(5) 0.0179(5) 0.0134(5) N(1) 0.0240(6) 0.0345(6) 0.0327(7) -0.0008(4) 0.0065(5) 0.0012(5) C(1) 0.0306(8) 0.0418(8) 0.0307(8) 0.0005(6) 0.0081(6) 0.0051(6) C(2) 0.0262(7) 0.0376(8) 0.0372(8) -0.0021(5) 0.0093(6) -0.0012(6) C(3) 0.0306(8) 0.0358(8) 0.0337(8) -0.0008(5) 0.0133(6) 0.0003(6) C(4) 0.0249(7) 0.0305(7) 0.0306(7) 0.0021(5) 0.0054(5) 0.0019(5) C(5) 0.0238(7) 0.0297(7) 0.0322(7) 0.0028(5) 0.0054(5) 0.0024(5) C(6) 0.0283(8) 0.0373(8) 0.0382(8) -0.0009(6) 0.0037(6) -0.0037(6) C(7) 0.0371(9) 0.0417(9) 0.0349(8) 0.0017(6) 0.0016(6) -0.0067(6) C(8) 0.0432(10) 0.0445(9) 0.0333(8) 0.0047(7) 0.0114(6) -0.0015(6) C(9) 0.0325(8) 0.0410(8) 0.0348(8) 0.0012(6) 0.0121(6) 0.0005(6) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # 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 F(1) C(1) 1.3422(18) yes . . O(1) C(2) 1.3152(18) yes . . O(2) C(3) 1.220(2) yes . . N(1) C(4) 1.3460(17) yes . . N(1) C(5) 1.347(2) yes . 3_665 C(1) C(2) 1.346(2) yes . . C(1) C(3) 1.446(2) yes . 3_555 C(2) C(3) 1.499(2) yes . . C(4) C(5) 1.433(2) yes . . C(4) C(9) 1.424(2) yes . . C(5) C(6) 1.4194(19) yes . . C(6) C(7) 1.364(2) yes . . C(7) C(8) 1.416(2) yes . . C(8) C(9) 1.356(2) yes . . O(1) H(1) 0.99(3) no . . C(6) H(2) 1.00(2) no . . C(7) H(3) 0.982(17) no . . C(8) H(4) 1.00(2) no . . C(9) H(5) 0.96(2) 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 C(4) N(1) C(5) 117.91(13) yes . . 3_665 F(1) C(1) C(2) 120.49(13) yes . . . F(1) C(1) C(3) 116.47(14) yes . . 3_555 C(2) C(1) C(3) 123.04(13) yes . . 3_555 O(1) C(2) C(1) 121.58(14) yes . . . O(1) C(2) C(3) 119.12(14) yes . . . C(1) C(2) C(3) 119.30(13) yes . . . O(2) C(3) C(1) 123.15(13) yes . . 3_555 O(2) C(3) C(2) 119.19(13) yes . . . C(1) C(3) C(2) 117.65(14) yes 3_555 . . N(1) C(4) C(5) 121.06(15) yes . . . N(1) C(4) C(9) 119.82(14) yes . . . C(5) C(4) C(9) 119.12(12) yes . . . N(1) C(5) C(4) 121.03(12) yes 3_665 . . N(1) C(5) C(6) 119.79(14) yes 3_665 . . C(4) C(5) C(6) 119.18(14) yes . . . C(5) C(6) C(7) 119.80(15) yes . . . C(6) C(7) C(8) 120.92(15) yes . . . C(7) C(8) C(9) 121.16(17) yes . . . C(4) C(9) C(8) 119.81(16) yes . . . C(2) O(1) H(1) 117.2(19) no . . . C(5) C(6) H(2) 117.4(11) no . . . C(7) C(6) H(2) 122.6(11) no . . . C(6) C(7) H(3) 118.3(12) no . . . C(8) C(7) H(3) 120.8(12) no . . . C(7) C(8) H(4) 116.6(11) no . . . C(9) C(8) H(4) 122.3(11) no . . . C(4) C(9) H(5) 117.6(12) no . . . C(8) C(9) H(5) 122.6(12) 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 C(4) N(1) C(5) C(4) -0.07(16) ? . . 3_665 3_665 C(4) N(1) C(5) C(6) 179.63(13) ? . . 3_665 3_665 C(5) N(1) C(4) C(5) 0.07(16) ? 3_665 . . . C(5) N(1) C(4) C(9) -179.81(13) ? 3_665 . . . F(1) C(1) C(2) O(1) 0.2(2) ? . . . . F(1) C(1) C(2) C(3) -179.92(13) ? . . . . F(1) C(1) C(3) O(2) -1.1(2) ? . . 3_555 3_555 F(1) C(1) C(3) C(2) 179.90(13) ? . . 3_555 3_555 C(2) C(1) C(3) O(2) 177.86(16) ? . . 3_555 3_555 C(2) C(1) C(3) C(2) -1.2(2) ? . . 3_555 3_555 C(3) C(1) C(2) O(1) -178.72(15) ? 3_555 . . . C(3) C(1) C(2) C(3) 1.2(2) ? 3_555 . . . O(1) C(2) C(3) O(2) -2.1(2) ? . . . . O(1) C(2) C(3) C(1) 178.78(14) ? . . . 3_555 C(1) C(2) C(3) O(2) 177.95(15) ? . . . . C(1) C(2) C(3) C(1) -1.1(2) ? . . . 3_555 N(1) C(4) C(5) N(1) -0.07(17) ? . . . 3_665 N(1) C(4) C(5) C(6) 179.63(13) ? . . . . N(1) C(4) C(9) C(8) 179.68(14) ? . . . . C(5) C(4) C(9) C(8) -0.2(2) ? . . . . C(9) C(4) C(5) N(1) 179.81(13) ? . . . 3_665 C(9) C(4) C(5) C(6) -0.5(2) ? . . . . N(1) C(5) C(6) C(7) -179.39(14) ? 3_665 . . . C(4) C(5) C(6) C(7) 0.9(2) ? . . . . C(5) C(6) C(7) C(8) -0.6(2) ? . . . . C(6) C(7) C(8) C(9) -0.1(2) ? . . . . C(7) C(8) C(9) C(4) 0.5(2) ? . . . . 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 F(1) O(1) 3.4974(18) ? . 1_545 F(1) C(1) 3.5300(19) ? . 1_545 F(1) C(2) 3.3507(19) ? . 1_545 F(1) C(8) 3.409(2) ? . 2_535 F(1) C(8) 3.474(2) ? . 2_545 O(1) F(1) 3.4974(18) ? . 1_565 O(1) N(1) 3.5671(19) ? . 1_545 O(1) N(1) 2.6966(19) ? . . O(1) C(4) 3.5059(19) ? . 1_545 O(1) C(4) 3.3994(19) ? . . O(1) C(9) 3.1757(19) ? . 1_545 O(1) C(9) 3.2675(19) ? . . O(2) N(1) 3.4096(16) ? . . O(2) C(2) 3.331(2) ? . 1_565 O(2) C(3) 3.398(2) ? . 1_565 O(2) C(6) 3.280(2) ? . 3_665 O(2) C(7) 3.457(2) ? . 4_464 O(2) C(8) 3.502(2) ? . 4_464 N(1) O(1) 2.6966(19) ? . . N(1) O(1) 3.5671(19) ? . 1_565 N(1) O(2) 3.4096(16) ? . . N(1) C(4) 3.4381(18) ? . 1_545 N(1) C(5) 3.4848(18) ? . 1_545 C(1) F(1) 3.5300(19) ? . 1_565 C(1) C(2) 3.414(2) ? . 1_545 C(1) C(3) 3.377(2) ? . 1_545 C(2) F(1) 3.3507(19) ? . 1_565 C(2) O(2) 3.331(2) ? . 1_545 C(2) C(1) 3.414(2) ? . 1_565 C(2) C(3) 3.535(2) ? . 1_545 C(3) O(2) 3.398(2) ? . 1_545 C(3) C(1) 3.377(2) ? . 1_565 C(3) C(2) 3.535(2) ? . 1_565 C(3) C(3) 3.502(2) ? . 3_565 C(4) O(1) 3.3994(19) ? . . C(4) O(1) 3.5059(19) ? . 1_565 C(4) N(1) 3.4381(18) ? . 1_565 C(4) C(6) 3.475(2) ? . 1_545 C(4) C(7) 3.576(2) ? . 1_545 C(5) N(1) 3.4848(18) ? . 1_565 C(5) C(5) 3.5414(19) ? . 3_675 C(5) C(6) 3.429(2) ? . 1_545 C(6) O(2) 3.280(2) ? . 3_665 C(6) C(4) 3.475(2) ? . 1_565 C(6) C(5) 3.429(2) ? . 1_565 C(7) O(2) 3.457(2) ? . 4_565 C(7) C(4) 3.576(2) ? . 1_565 C(7) C(9) 3.482(2) ? . 1_565 C(8) F(1) 3.474(2) ? . 2_555 C(8) F(1) 3.409(2) ? . 2_565 C(8) O(2) 3.502(2) ? . 4_565 C(8) C(9) 3.443(2) ? . 1_565 C(9) O(1) 3.2675(19) ? . . C(9) O(1) 3.1757(19) ? . 1_565 C(9) C(7) 3.482(2) ? . 1_545 C(9) C(8) 3.443(2) ? . 1_545 F(1) H(4) 2.60(2) ? . 2_535 F(1) H(4) 2.84(2) ? . 2_545 F(1) H(5) 3.25(2) ? . 1_545 F(1) H(5) 3.26(2) ? . 2_545 O(1) H(1) 3.43(2) ? . 1_545 O(1) H(2) 3.32(2) ? . 3_665 O(1) H(5) 2.905(18) ? . 1_545 O(1) H(5) 2.555(18) ? . . O(2) H(2) 2.45(2) ? . 3_665 O(2) H(3) 2.79(2) ? . 4_464 O(2) H(4) 3.348(19) ? . 4_454 O(2) H(4) 2.817(19) ? . 4_464 N(1) H(1) 1.80(4) ? . . N(1) H(1) 3.55(3) ? . 1_565 C(1) H(4) 3.50(2) ? . 2_535 C(1) H(4) 3.09(2) ? . 2_545 C(3) H(2) 3.29(2) ? . 3_665 C(3) H(4) 3.31(2) ? . 4_454 C(3) H(4) 3.52(2) ? . 4_464 C(4) H(1) 2.70(3) ? . . C(4) H(1) 3.46(3) ? . 1_565 C(5) H(1) 2.78(4) ? . 3_665 C(5) H(2) 3.447(18) ? . 1_545 C(6) H(1) 3.07(3) ? . 3_665 C(6) H(3) 2.895(16) ? . 2_645 C(6) H(3) 3.583(16) ? . 2_655 C(7) H(2) 3.413(18) ? . 2_645 C(7) H(2) 3.574(18) ? . 2_655 C(7) H(3) 3.505(17) ? . 1_545 C(7) H(3) 3.053(17) ? . 2_645 C(7) H(3) 3.567(17) ? . 2_655 C(8) H(3) 3.463(17) ? . 1_545 C(8) H(5) 3.418(18) ? . 1_565 C(9) H(1) 2.92(3) ? . . C(9) H(1) 3.44(2) ? . 1_565 H(1) O(1) 3.43(2) ? . 1_565 H(1) N(1) 3.55(3) ? . 1_545 H(1) N(1) 1.80(4) ? . . H(1) C(4) 3.46(3) ? . 1_545 H(1) C(4) 2.70(3) ? . . H(1) C(5) 2.78(4) ? . 3_665 H(1) C(6) 3.07(3) ? . 3_665 H(1) C(9) 3.44(2) ? . 1_545 H(1) C(9) 2.92(3) ? . . H(1) H(2) 2.59(4) ? . 3_665 H(1) H(5) 3.43(3) ? . 1_545 H(1) H(5) 2.43(3) ? . . H(2) O(1) 3.32(2) ? . 3_665 H(2) O(2) 2.45(2) ? . 3_665 H(2) C(3) 3.29(2) ? . 3_665 H(2) C(5) 3.447(18) ? . 1_565 H(2) C(7) 3.574(18) ? . 2_645 H(2) C(7) 3.413(18) ? . 2_655 H(2) H(1) 2.59(4) ? . 3_665 H(2) H(3) 2.61(2) ? . 2_645 H(2) H(3) 3.01(2) ? . 2_655 H(3) O(2) 2.79(2) ? . 4_565 H(3) C(6) 3.583(16) ? . 2_645 H(3) C(6) 2.895(16) ? . 2_655 H(3) C(7) 3.505(17) ? . 1_565 H(3) C(7) 3.567(17) ? . 2_645 H(3) C(7) 3.053(17) ? . 2_655 H(3) C(8) 3.463(17) ? . 1_565 H(3) H(2) 3.01(2) ? . 2_645 H(3) H(2) 2.61(2) ? . 2_655 H(3) H(3) 2.91(2) ? . 2_645 H(3) H(3) 2.91(2) ? . 2_655 H(4) F(1) 2.84(2) ? . 2_555 H(4) F(1) 2.60(2) ? . 2_565 H(4) O(2) 3.348(19) ? . 4_555 H(4) O(2) 2.817(19) ? . 4_565 H(4) C(1) 3.09(2) ? . 2_555 H(4) C(1) 3.50(2) ? . 2_565 H(4) C(3) 3.31(2) ? . 4_555 H(4) C(3) 3.52(2) ? . 4_565 H(4) H(5) 3.53(2) ? . 1_565 H(5) F(1) 3.25(2) ? . 1_565 H(5) F(1) 3.26(2) ? . 2_555 H(5) O(1) 2.555(18) ? . . H(5) O(1) 2.905(18) ? . 1_565 H(5) C(8) 3.418(18) ? . 1_545 H(5) H(1) 2.43(3) ? . . H(5) H(1) 3.43(3) ? . 1_565 H(5) H(4) 3.53(2) ? . 1_545 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1) O(2) . . . 2.7359(17) 0.99(3) 2.37(3) 101(2) no O(1) H(1) N(1) . . . 2.6966(19) 0.99(3) 1.80(4) 150(2) no #============================================================================== data__Phz-H2fa(gamma-form) _database_code_depnum_ccdc_archive 'CCDC 716154' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H10 F2 N2 O4 ' _chemical_formula_moiety 'C18 H10 F2 N2 O4 ' _chemical_formula_weight 356.28 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 4.0812(19) _cell_length_b 8.938(4) _cell_length_c 11.581(4) _cell_angle_alpha 73.07(3) _cell_angle_beta 78.91(3) _cell_angle_gamma 79.57(3) _cell_volume 393.1(3) _cell_formula_units_Z 1 _cell_measurement_reflns_used 1349 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 293.1 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 182.00 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.749 _exptl_absorpt_correction_T_max 0.991 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 3915 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.967 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1745 _reflns_number_gt 949 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.0730 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 949 _refine_ls_number_parameters 126 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0043Fo^2^ + 1.0000\s(Fo^2^)]' _refine_ls_shift/su_max 0.1148 _refine_diff_density_max 0.15 _refine_diff_density_min -0.17 _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 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; 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 F(1) F 0.7732(5) 0.2008(2) 0.58263(14) 0.0600(6) Uani 1.00 1 d . . . O(1) O 0.7159(6) 0.2738(2) 0.34162(19) 0.0554(6) Uani 1.00 1 d . . . O(2) O 0.4453(6) 0.0641(2) 0.26494(17) 0.0567(6) Uani 1.00 1 d . . . N(1) N 0.5739(6) 0.4075(2) 0.11534(18) 0.0399(6) Uani 1.00 1 d . . . C(1) C 0.6397(7) 0.1065(3) 0.5382(2) 0.0394(7) Uani 1.00 1 d . . . C(2) C 0.6125(6) 0.1434(3) 0.4193(2) 0.0378(7) Uani 1.00 1 d . . . C(3) C 0.4694(6) 0.0344(3) 0.3735(2) 0.0402(7) Uani 1.00 1 d . . . C(4) C 0.3454(7) 0.5369(3) 0.1048(2) 0.0372(7) Uani 1.00 1 d . . . C(5) C 0.2666(7) 0.6313(3) -0.0127(2) 0.0367(7) Uani 1.00 1 d . . . C(6) C 0.0219(7) 0.7672(3) -0.0192(2) 0.0459(8) Uani 1.00 1 d . . . C(7) C -0.1347(8) 0.8063(3) 0.0839(2) 0.0517(9) Uani 1.00 1 d . . . C(8) C -0.0576(8) 0.7136(4) 0.1993(2) 0.0538(10) Uani 1.00 1 d . . . C(9) C 0.1721(8) 0.5823(4) 0.2108(2) 0.0474(8) Uani 1.00 1 d . . . H(1) H -0.0322 0.8299 -0.0964 0.054 Uiso 1.00 1 c R . . H(2) H -0.2975 0.8977 0.0786 0.062 Uiso 1.00 1 c R . . H(3) H -0.1698 0.7437 0.2705 0.067 Uiso 1.00 1 c R . . H(4) H 0.2176 0.5202 0.2893 0.058 Uiso 1.00 1 c R . . H(5) H 0.653(9) 0.292(4) 0.261(3) 0.082(11) Uiso 1.00 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0797(14) 0.0658(12) 0.0449(9) -0.0245(10) -0.0156(8) -0.0179(8) O(1) 0.0791(16) 0.0553(13) 0.0323(10) -0.0190(12) -0.0137(9) -0.0027(9) O(2) 0.0827(16) 0.0604(14) 0.0295(10) -0.0148(12) -0.0166(9) -0.0072(9) N(1) 0.0508(14) 0.0385(13) 0.0306(11) -0.0139(12) -0.0076(9) -0.0039(9) C(1) 0.0402(16) 0.0464(16) 0.0371(14) -0.0048(13) -0.0092(10) -0.0180(12) C(2) 0.0376(16) 0.0410(15) 0.0323(14) -0.0023(12) -0.0059(10) -0.0072(11) C(3) 0.0408(16) 0.0492(16) 0.0276(13) 0.0057(13) -0.0074(10) -0.0111(12) C(4) 0.0483(17) 0.0352(15) 0.0301(13) -0.0145(14) -0.0064(10) -0.0061(11) C(5) 0.0470(16) 0.0329(14) 0.0316(13) -0.0147(13) -0.0078(10) -0.0038(10) C(6) 0.0530(19) 0.0399(16) 0.0424(15) -0.0109(14) -0.0092(12) -0.0032(12) C(7) 0.052(2) 0.0455(18) 0.0571(19) -0.0072(16) -0.0043(14) -0.0151(15) C(8) 0.058(2) 0.060(2) 0.0502(18) -0.0144(18) -0.0024(14) -0.0237(15) C(9) 0.0565(19) 0.0542(19) 0.0343(14) -0.0145(16) -0.0075(12) -0.0112(13) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # 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 F(1) C(1) 1.341(4) yes . . O(1) C(2) 1.330(3) yes . . O(2) C(3) 1.227(3) yes . . N(1) C(4) 1.339(3) yes . . N(1) C(5) 1.348(3) yes . 2_665 C(1) C(2) 1.341(3) yes . . C(1) C(3) 1.452(3) yes . 2_656 C(2) C(3) 1.482(4) yes . . C(4) C(5) 1.438(3) yes . . C(4) C(9) 1.423(4) yes . . C(5) C(6) 1.420(3) yes . . C(6) C(7) 1.350(4) yes . . C(7) C(8) 1.412(4) yes . . C(8) C(9) 1.354(4) yes . . O(1) H(5) 0.97(4) no . . C(6) H(1) 0.950 no . . C(7) H(2) 0.950 no . . C(8) H(3) 0.950 no . . C(9) H(4) 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 C(4) N(1) C(5) 118.4(2) yes . . 2_665 F(1) C(1) C(2) 120.8(2) yes . . . F(1) C(1) C(3) 115.7(2) yes . . 2_656 C(2) C(1) C(3) 123.5(3) yes . . 2_656 O(1) C(2) C(1) 121.5(3) yes . . . O(1) C(2) C(3) 119.5(2) yes . . . C(1) C(2) C(3) 119.0(2) yes . . . O(2) C(3) C(1) 122.1(3) yes . . 2_656 O(2) C(3) C(2) 120.4(2) yes . . . C(1) C(3) C(2) 117.4(2) yes 2_656 . . N(1) C(4) C(5) 121.1(2) yes . . . N(1) C(4) C(9) 120.2(2) yes . . . C(5) C(4) C(9) 118.7(2) yes . . . N(1) C(5) C(4) 120.5(2) yes 2_665 . . N(1) C(5) C(6) 120.4(2) yes 2_665 . . C(4) C(5) C(6) 119.1(2) yes . . . C(5) C(6) C(7) 120.2(2) yes . . . C(6) C(7) C(8) 120.8(2) yes . . . C(7) C(8) C(9) 121.5(3) yes . . . C(4) C(9) C(8) 119.8(2) yes . . . C(2) O(1) H(5) 112(2) no . . . C(5) C(6) H(1) 119.6 no . . . C(7) C(6) H(1) 120.3 no . . . C(6) C(7) H(2) 119.6 no . . . C(8) C(7) H(2) 119.6 no . . . C(7) C(8) H(3) 119.4 no . . . C(9) C(8) H(3) 119.2 no . . . C(4) C(9) H(4) 119.9 no . . . C(8) C(9) H(4) 120.3 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 C(4) N(1) C(5) C(4) -1.0(4) ? . . 2_665 2_665 C(4) N(1) C(5) C(6) 179.9(2) ? . . 2_665 2_665 C(5) N(1) C(4) C(5) 1.0(4) ? 2_665 . . . C(5) N(1) C(4) C(9) -179.8(3) ? 2_665 . . . F(1) C(1) C(2) O(1) -0.0(3) ? . . . . F(1) C(1) C(2) C(3) 178.8(2) ? . . . . F(1) C(1) C(3) O(2) 0.9(3) ? . . 2_656 2_656 F(1) C(1) C(3) C(2) -178.9(2) ? . . 2_656 2_656 C(2) C(1) C(3) O(2) -179.1(2) ? . . 2_656 2_656 C(2) C(1) C(3) C(2) 1.1(3) ? . . 2_656 2_656 C(3) C(1) C(2) O(1) 180.0(2) ? 2_656 . . . C(3) C(1) C(2) C(3) -1.1(4) ? 2_656 . . . O(1) C(2) C(3) O(2) -0.2(3) ? . . . . O(1) C(2) C(3) C(1) 179.96(18) ? . . . 2_656 C(1) C(2) C(3) O(2) -179.1(2) ? . . . . C(1) C(2) C(3) C(1) 1.1(3) ? . . . 2_656 N(1) C(4) C(5) N(1) -1.0(4) ? . . . 2_665 N(1) C(4) C(5) C(6) 179.9(3) ? . . . . N(1) C(4) C(9) C(8) 179.7(3) ? . . . . C(5) C(4) C(9) C(8) -1.1(5) ? . . . . C(9) C(4) C(5) N(1) 179.8(3) ? . . . 2_665 C(9) C(4) C(5) C(6) 0.7(4) ? . . . . N(1) C(5) C(6) C(7) -179.4(3) ? 2_665 . . . C(4) C(5) C(6) C(7) -0.3(5) ? . . . . C(5) C(6) C(7) C(8) 0.3(5) ? . . . . C(6) C(7) C(8) C(9) -0.7(5) ? . . . . C(7) C(8) C(9) C(4) 1.1(5) ? . . . . 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 F(1) C(1) 3.458(3) ? . 1_655 F(1) C(3) 3.444(3) ? . 2_756 F(1) C(8) 3.300(4) ? . 2_666 F(1) C(9) 3.549(4) ? . 2_666 O(1) O(2) 3.331(3) ? . 1_655 O(1) N(1) 2.672(2) ? . . O(1) C(3) 3.431(3) ? . 1_655 O(1) C(4) 3.448(3) ? . . O(1) C(9) 3.386(3) ? . . O(1) C(9) 3.420(4) ? . 1_655 O(2) O(1) 3.331(3) ? . 1_455 O(2) N(1) 3.136(3) ? . . O(2) C(2) 3.574(3) ? . 1_455 O(2) C(5) 3.541(3) ? . 2_665 O(2) C(6) 3.544(3) ? . 2_565 O(2) C(6) 3.378(3) ? . 2_665 O(2) C(7) 3.557(4) ? . 1_645 N(1) O(1) 2.672(2) ? . . N(1) O(2) 3.136(3) ? . . N(1) C(4) 3.515(4) ? . 1_655 N(1) C(5) 3.591(3) ? . 1_655 C(1) F(1) 3.458(3) ? . 1_455 C(1) C(1) 3.318(3) ? . 2_756 C(1) C(2) 3.466(3) ? . 2_756 C(2) O(2) 3.574(3) ? . 1_655 C(2) C(1) 3.466(3) ? . 2_756 C(2) C(3) 3.438(3) ? . 1_655 C(3) F(1) 3.444(3) ? . 2_756 C(3) O(1) 3.431(3) ? . 1_455 C(3) C(2) 3.438(3) ? . 1_455 C(4) O(1) 3.448(3) ? . . C(4) N(1) 3.515(4) ? . 1_455 C(4) C(5) 3.599(4) ? . 2_565 C(4) C(6) 3.568(4) ? . 1_655 C(4) C(7) 3.416(4) ? . 1_655 C(5) O(2) 3.541(3) ? . 2_665 C(5) N(1) 3.591(3) ? . 1_455 C(5) C(4) 3.599(4) ? . 2_565 C(5) C(5) 3.395(4) ? . 2_565 C(5) C(6) 3.493(4) ? . 1_655 C(6) O(2) 3.544(3) ? . 2_565 C(6) O(2) 3.378(3) ? . 2_665 C(6) C(4) 3.568(4) ? . 1_455 C(6) C(5) 3.493(4) ? . 1_455 C(7) O(2) 3.557(4) ? . 1_465 C(7) C(4) 3.416(4) ? . 1_455 C(7) C(9) 3.593(4) ? . 1_455 C(8) F(1) 3.300(4) ? . 2_666 C(8) C(9) 3.516(5) ? . 1_455 C(9) F(1) 3.549(4) ? . 2_666 C(9) O(1) 3.420(4) ? . 1_455 C(9) O(1) 3.386(3) ? . . C(9) C(7) 3.593(4) ? . 1_655 C(9) C(8) 3.516(5) ? . 1_655 F(1) H(3) 2.764 ? . 2_566 F(1) H(3) 2.757 ? . 2_666 F(1) H(4) 3.260 ? . 2_666 O(1) H(1) 3.206 ? . 2_665 O(1) H(4) 2.725 ? . . O(1) H(4) 3.128 ? . 1_655 O(2) H(1) 2.676 ? . 2_565 O(2) H(1) 2.897 ? . 2_665 O(2) H(2) 2.900 ? . 1_645 O(2) H(3) 2.996 ? . 1_645 O(2) H(5) 3.49(3) ? . 1_455 N(1) H(1) 3.405 ? . 2_565 N(1) H(5) 1.76(4) ? . . C(1) H(3) 3.089 ? . 2_566 C(2) H(4) 3.496 ? . . C(3) H(1) 3.599 ? . 2_665 C(3) H(3) 3.175 ? . 1_645 C(4) H(5) 2.69(3) ? . . C(5) H(1) 3.471 ? . 1_655 C(5) H(5) 2.73(4) ? . 2_665 C(6) H(2) 3.230 ? . 2_575 C(6) H(5) 3.01(4) ? . 2_665 C(7) H(1) 3.489 ? . 2_575 C(7) H(2) 3.531 ? . 2_475 C(7) H(2) 3.342 ? . 2_575 C(8) H(4) 3.527 ? . 1_455 C(9) H(3) 3.532 ? . 1_655 C(9) H(5) 3.49(4) ? . 1_455 C(9) H(5) 2.94(3) ? . . H(1) O(1) 3.206 ? . 2_665 H(1) O(2) 2.676 ? . 2_565 H(1) O(2) 2.897 ? . 2_665 H(1) N(1) 3.405 ? . 2_565 H(1) C(3) 3.599 ? . 2_665 H(1) C(5) 3.471 ? . 1_455 H(1) C(7) 3.489 ? . 2_575 H(1) H(2) 3.334 ? . 2_475 H(1) H(2) 3.061 ? . 2_575 H(1) H(5) 2.585 ? . 2_665 H(2) O(2) 2.900 ? . 1_465 H(2) C(6) 3.230 ? . 2_575 H(2) C(7) 3.531 ? . 2_475 H(2) C(7) 3.342 ? . 2_575 H(2) H(1) 3.334 ? . 2_475 H(2) H(1) 3.061 ? . 2_575 H(2) H(2) 2.741 ? . 2_475 H(2) H(2) 3.244 ? . 2_575 H(3) F(1) 2.764 ? . 2_566 H(3) F(1) 2.757 ? . 2_666 H(3) O(2) 2.996 ? . 1_465 H(3) C(1) 3.089 ? . 2_566 H(3) C(3) 3.175 ? . 1_465 H(3) C(9) 3.532 ? . 1_455 H(3) H(4) 3.411 ? . 1_455 H(4) F(1) 3.260 ? . 2_666 H(4) O(1) 3.128 ? . 1_455 H(4) O(1) 2.725 ? . . H(4) C(2) 3.496 ? . . H(4) C(8) 3.527 ? . 1_655 H(4) H(3) 3.411 ? . 1_655 H(4) H(5) 3.456 ? . 1_455 H(4) H(5) 2.506 ? . . H(5) O(2) 3.49(3) ? . 1_655 H(5) N(1) 1.76(4) ? . . H(5) C(4) 2.69(3) ? . . H(5) C(5) 2.73(4) ? . 2_665 H(5) C(6) 3.01(4) ? . 2_665 H(5) C(9) 2.94(3) ? . . H(5) C(9) 3.49(4) ? . 1_655 H(5) H(1) 2.585 ? . 2_665 H(5) H(4) 2.506 ? . . H(5) H(4) 3.456 ? . 1_655 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(5) O(2) . . . 2.760(3) 0.97(4) 2.33(4) 106(2) no O(1) H(5) N(1) . . . 2.672(2) 0.97(4) 1.76(4) 155(3) no #============================================================================== data___Phz-H2ba(beta-form) _database_code_depnum_ccdc_archive 'CCDC 716155' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H10 Br2 N2 O4 ' _chemical_formula_moiety 'C18 H10 Br2 N2 O4 ' _chemical_formula_weight 478.10 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 12.299(2) _cell_length_b 4.8114(8) _cell_length_c 15.153(3) _cell_angle_alpha 90.0000 _cell_angle_beta 107.6042(17) _cell_angle_gamma 90.0000 _cell_volume 854.7(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2938 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 293.1 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.858 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468.00 _exptl_absorpt_coefficient_mu 4.784 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.354 _exptl_absorpt_correction_T_max 0.826 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 8159 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1924 _reflns_number_gt 1308 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.0499 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 1325 _refine_ls_number_parameters 127 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0007Fo^2^ + 1.0000\s(Fo^2^)]' _refine_ls_shift/su_max 0.0094 _refine_diff_density_max 0.87 _refine_diff_density_min -0.57 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 19(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Br Br -0.290 2.459 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; 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 Br(1) Br 0.56644(4) 0.04733(11) 0.67311(4) 0.05553(18) Uani 1.00 1 d . . . O(1) O 0.3353(2) 0.2897(7) 0.5696(2) 0.0627(11) Uani 1.00 1 d . . . O(2) O 0.2838(2) 0.6459(8) 0.4254(2) 0.0695(12) Uani 1.00 1 d . . . N(1) N 0.1162(2) 0.4405(7) 0.5186(2) 0.0422(10) Uani 1.00 1 d . . . C(1) C 0.5262(3) 0.3009(8) 0.5745(3) 0.0413(12) Uani 1.00 1 d . . . C(2) C 0.4170(3) 0.3834(9) 0.5384(3) 0.0436(12) Uani 1.00 1 d . . . C(3) C 0.3844(3) 0.5862(9) 0.4589(3) 0.0450(13) Uani 1.00 1 d . . . C(4) C 0.0379(3) 0.3026(8) 0.4527(3) 0.0408(12) Uani 1.00 1 d . . . C(5) C 0.0708(4) 0.0896(9) 0.4013(3) 0.0538(15) Uani 1.00 1 d . . . C(6) C -0.0087(6) -0.0474(11) 0.3357(4) 0.071(2) Uani 1.00 1 d . . . C(7) C -0.1245(6) 0.0101(11) 0.3158(4) 0.0712(19) Uani 1.00 1 d . . . C(8) C -0.1612(4) 0.2102(10) 0.3631(3) 0.0579(15) Uani 1.00 1 d . . . C(9) C -0.0810(3) 0.3628(9) 0.4333(3) 0.0423(12) Uani 1.00 1 d . . . H(1) H 0.268(5) 0.381(12) 0.543(4) 0.09(2) Uiso 1.00 1 d . . . H(2) H 0.1491 0.0440 0.4133 0.068 Uiso 1.00 1 c R . . H(3) H 0.0147 -0.1889 0.3016 0.089 Uiso 1.00 1 c R . . H(4) H -0.1784 -0.0915 0.2686 0.084 Uiso 1.00 1 c R . . H(5) H -0.2405 0.2479 0.3492 0.066 Uiso 1.00 1 c 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 Br(1) 0.0532(3) 0.0564(3) 0.0545(3) 0.0064(2) 0.0124(2) 0.0112(2) O(1) 0.0331(16) 0.078(2) 0.080(2) 0.0066(17) 0.0226(18) 0.030(2) O(2) 0.0346(16) 0.094(2) 0.081(2) 0.0189(18) 0.0187(18) 0.033(2) N(1) 0.0314(17) 0.050(2) 0.048(2) 0.0011(16) 0.0159(17) 0.0101(18) C(1) 0.035(2) 0.041(2) 0.045(2) 0.0020(18) 0.009(2) 0.0000(19) C(2) 0.035(2) 0.044(2) 0.054(2) -0.0015(19) 0.018(2) -0.000(2) C(3) 0.033(2) 0.048(2) 0.053(2) 0.0060(19) 0.012(2) 0.002(2) C(4) 0.040(2) 0.043(2) 0.044(2) 0.0027(19) 0.020(2) 0.009(2) C(5) 0.066(3) 0.050(2) 0.055(3) 0.012(2) 0.032(2) 0.009(2) C(6) 0.120(5) 0.053(3) 0.051(3) 0.004(3) 0.041(3) 0.001(2) C(7) 0.100(4) 0.066(3) 0.043(3) -0.022(3) 0.014(3) -0.006(2) C(8) 0.057(2) 0.056(3) 0.054(3) -0.009(2) 0.006(2) 0.011(2) C(9) 0.040(2) 0.045(2) 0.043(2) -0.0021(19) 0.014(2) 0.007(2) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # 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 Br(1) C(1) 1.876(4) yes . . O(1) C(2) 1.313(6) yes . . O(2) C(3) 1.221(4) yes . . N(1) C(4) 1.335(5) yes . . N(1) C(9) 1.343(6) yes . 3_566 C(1) C(2) 1.347(5) yes . . C(1) C(3) 1.449(6) yes . 3_666 C(2) C(3) 1.507(6) yes . . C(4) C(5) 1.420(7) yes . . C(4) C(9) 1.431(6) yes . . C(5) C(6) 1.339(7) yes . . C(6) C(7) 1.391(11) yes . . C(7) C(8) 1.356(8) yes . . C(8) C(9) 1.418(6) yes . . O(1) H(1) 0.92(5) no . . C(5) H(2) 0.950 no . . C(6) H(3) 0.950 no . . C(7) H(4) 0.950 no . . C(8) H(5) 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 C(4) N(1) C(9) 118.5(3) yes . . 3_566 Br(1) C(1) C(2) 120.4(3) yes . . . Br(1) C(1) C(3) 118.5(2) yes . . 3_666 C(2) C(1) C(3) 121.1(4) yes . . 3_666 O(1) C(2) C(1) 122.0(4) yes . . . O(1) C(2) C(3) 117.5(3) yes . . . C(1) C(2) C(3) 120.5(4) yes . . . O(2) C(3) C(1) 123.2(4) yes . . 3_666 O(2) C(3) C(2) 118.5(4) yes . . . C(1) C(3) C(2) 118.4(3) yes 3_666 . . N(1) C(4) C(5) 120.5(4) yes . . . N(1) C(4) C(9) 121.0(4) yes . . . C(5) C(4) C(9) 118.5(3) yes . . . C(4) C(5) C(6) 119.8(5) yes . . . C(5) C(6) C(7) 122.2(6) yes . . . C(6) C(7) C(8) 120.6(5) yes . . . C(7) C(8) C(9) 119.8(5) yes . . . N(1) C(9) C(4) 120.5(3) yes 3_566 . . N(1) C(9) C(8) 120.4(4) yes 3_566 . . C(4) C(9) C(8) 119.0(4) yes . . . C(2) O(1) H(1) 111(4) no . . . C(4) C(5) H(2) 120.2 no . . . C(6) C(5) H(2) 120.0 no . . . C(5) C(6) H(3) 118.8 no . . . C(7) C(6) H(3) 119.0 no . . . C(6) C(7) H(4) 119.7 no . . . C(8) C(7) H(4) 119.7 no . . . C(7) C(8) H(5) 120.1 no . . . C(9) C(8) H(5) 120.1 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 C(4) N(1) C(9) C(4) -0.2(5) ? . . 3_566 3_566 C(4) N(1) C(9) C(8) -179.7(4) ? . . 3_566 3_566 C(9) N(1) C(4) C(5) -178.9(4) ? 3_566 . . . C(9) N(1) C(4) C(9) 0.2(5) ? 3_566 . . . Br(1) C(1) C(2) O(1) -0.6(6) ? . . . . Br(1) C(1) C(2) C(3) -179.7(3) ? . . . . Br(1) C(1) C(3) O(2) -0.8(6) ? . . 3_666 3_666 Br(1) C(1) C(3) C(2) 179.8(3) ? . . 3_666 3_666 C(2) C(1) C(3) O(2) 176.6(4) ? . . 3_666 3_666 C(2) C(1) C(3) C(2) -2.8(6) ? . . 3_666 3_666 C(3) C(1) C(2) O(1) -178.0(4) ? 3_666 . . . C(3) C(1) C(2) C(3) 2.9(6) ? 3_666 . . . O(1) C(2) C(3) O(2) -2.5(6) ? . . . . O(1) C(2) C(3) C(1) 178.0(4) ? . . . 3_666 C(1) C(2) C(3) O(2) 176.7(4) ? . . . . C(1) C(2) C(3) C(1) -2.8(6) ? . . . 3_666 N(1) C(4) C(5) C(6) 179.8(5) ? . . . . N(1) C(4) C(9) N(1) -0.2(5) ? . . . 3_566 N(1) C(4) C(9) C(8) -179.7(4) ? . . . . C(5) C(4) C(9) N(1) 178.9(4) ? . . . 3_566 C(5) C(4) C(9) C(8) -0.6(7) ? . . . . C(9) C(4) C(5) C(6) 0.7(7) ? . . . . C(4) C(5) C(6) C(7) -0.3(8) ? . . . . C(5) C(6) C(7) C(8) -0.1(7) ? . . . . C(6) C(7) C(8) C(9) 0.2(7) ? . . . . C(7) C(8) C(9) N(1) -179.3(5) ? . . . 3_566 C(7) C(8) C(9) C(4) 0.2(6) ? . . . . 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 O(1) N(1) 2.670(4) ? . . O(1) C(4) 3.551(4) ? . . O(1) C(8) 3.568(6) ? . 3_556 O(1) C(8) 3.569(6) ? . 3_566 O(1) C(9) 3.535(5) ? . 3_566 O(2) N(1) 2.996(5) ? . . O(2) C(4) 3.579(5) ? . . O(2) C(5) 3.313(6) ? . 1_565 N(1) O(1) 2.670(4) ? . . N(1) O(2) 2.996(5) ? . . N(1) C(5) 3.554(6) ? . 1_565 N(1) C(6) 3.459(8) ? . 3_556 N(1) C(7) 3.294(7) ? . 3_556 N(1) C(8) 3.566(6) ? . 3_556 C(4) O(1) 3.551(4) ? . . C(4) O(2) 3.579(5) ? . . C(4) C(4) 3.494(6) ? . 3_556 C(4) C(5) 3.469(7) ? . 3_556 C(4) C(6) 3.555(7) ? . 1_565 C(4) C(6) 3.551(8) ? . 3_556 C(4) C(9) 3.600(6) ? . 3_556 C(5) O(2) 3.313(6) ? . 1_545 C(5) N(1) 3.554(6) ? . 1_545 C(5) C(4) 3.469(7) ? . 3_556 C(5) C(9) 3.294(7) ? . 3_556 C(6) N(1) 3.459(8) ? . 3_556 C(6) C(4) 3.555(7) ? . 1_545 C(6) C(4) 3.551(8) ? . 3_556 C(6) C(6) 3.594(9) ? . 2_545 C(6) C(6) 3.594(9) ? . 2_555 C(6) C(9) 3.439(8) ? . 1_545 C(7) N(1) 3.294(7) ? . 3_556 C(7) C(9) 3.547(7) ? . 1_545 C(8) O(1) 3.568(6) ? . 3_556 C(8) O(1) 3.569(6) ? . 3_566 C(8) N(1) 3.566(6) ? . 3_556 C(9) O(1) 3.535(5) ? . 3_566 C(9) C(4) 3.600(6) ? . 3_556 C(9) C(5) 3.294(7) ? . 3_556 C(9) C(6) 3.439(8) ? . 1_565 C(9) C(7) 3.547(7) ? . 1_565 Br(1) H(5) 3.146 ? . 4_655 O(1) H(2) 2.995 ? . . O(1) H(5) 3.230 ? . 3_556 O(1) H(5) 2.949 ? . 3_566 O(2) H(2) 3.314 ? . . O(2) H(2) 2.502 ? . 1_565 O(2) H(3) 3.369 ? . 1_565 O(2) H(4) 3.054 ? . 2_555 N(1) H(1) 1.81(6) ? . . N(1) H(2) 3.396 ? . 1_565 N(1) H(4) 3.508 ? . 3_556 C(3) H(2) 3.534 ? . 1_565 C(4) H(1) 2.77(5) ? . . C(4) H(3) 3.304 ? . 1_565 C(5) H(1) 3.05(5) ? . . C(5) H(3) 3.121 ? . 2_555 C(5) H(4) 3.576 ? . 2_555 C(6) H(3) 2.687 ? . 2_555 C(7) H(3) 2.923 ? . 2_555 C(8) H(1) 2.96(7) ? . 3_566 C(8) H(2) 3.563 ? . 3_556 C(8) H(3) 3.526 ? . 2_555 C(9) H(1) 2.73(6) ? . 3_566 C(9) H(2) 3.334 ? . 3_556 C(9) H(3) 3.383 ? . 1_565 C(9) H(4) 3.570 ? . 1_565 H(1) N(1) 1.81(6) ? . . H(1) C(4) 2.77(5) ? . . H(1) C(5) 3.05(5) ? . . H(1) C(8) 2.96(7) ? . 3_566 H(1) C(9) 2.73(6) ? . 3_566 H(1) H(2) 2.624 ? . . H(1) H(5) 3.504 ? . 3_556 H(1) H(5) 2.512 ? . 3_566 H(2) O(1) 2.995 ? . . H(2) O(2) 2.502 ? . 1_545 H(2) O(2) 3.314 ? . . H(2) N(1) 3.396 ? . 1_545 H(2) C(3) 3.534 ? . 1_545 H(2) C(8) 3.563 ? . 3_556 H(2) C(9) 3.334 ? . 3_556 H(2) H(1) 2.624 ? . . H(2) H(3) 3.514 ? . 2_555 H(2) H(4) 3.376 ? . 2_555 H(3) O(2) 3.369 ? . 1_545 H(3) C(4) 3.304 ? . 1_545 H(3) C(5) 3.121 ? . 2_545 H(3) C(6) 2.687 ? . 2_545 H(3) C(7) 2.923 ? . 2_545 H(3) C(8) 3.526 ? . 2_545 H(3) C(9) 3.383 ? . 1_545 H(3) H(2) 3.514 ? . 2_545 H(3) H(3) 2.833 ? . 2_545 H(3) H(3) 2.833 ? . 2_555 H(3) H(4) 3.199 ? . 2_545 H(4) O(2) 3.054 ? . 2_545 H(4) N(1) 3.508 ? . 3_556 H(4) C(5) 3.576 ? . 2_545 H(4) C(9) 3.570 ? . 1_545 H(4) H(2) 3.376 ? . 2_545 H(4) H(3) 3.199 ? . 2_555 H(4) H(5) 3.569 ? . 1_545 H(5) Br(1) 3.146 ? . 4_454 H(5) O(1) 3.230 ? . 3_556 H(5) O(1) 2.949 ? . 3_566 H(5) H(1) 3.504 ? . 3_556 H(5) H(1) 2.512 ? . 3_566 H(5) H(4) 3.569 ? . 1_565 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1) O(2) . . . 2.697(5) 0.92(5) 2.24(7) 110(5) no O(1) H(1) N(1) . . . 2.670(4) 0.92(5) 1.81(6) 155(6) no #============================================================================== data__Phz-H2ia(beta-form) _database_code_depnum_ccdc_archive 'CCDC 716156' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H10 I2 N2 O4 ' _chemical_formula_moiety 'C18 H10 I2 N2 O4 ' _chemical_formula_weight 572.10 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 12.300(4) _cell_length_b 4.9829(13) _cell_length_c 15.271(5) _cell_angle_alpha 90.0000 _cell_angle_beta 106.939(6) _cell_angle_gamma 90.0000 _cell_volume 895.3(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3351 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 293.1 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 2.122 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540.00 _exptl_absorpt_coefficient_mu 3.540 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.606 _exptl_absorpt_correction_T_max 0.838 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 8545 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2037 _reflns_number_gt 1503 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0203 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 1503 _refine_ls_number_parameters 127 _refine_ls_goodness_of_fit_ref 1.815 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/\s^2^(Fo)' _refine_ls_shift/su_max 0.0025 _refine_diff_density_max 0.56 _refine_diff_density_min -0.61 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 10(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; I I -0.474 1.812 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; 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 I(1) I 0.56837(2) 0.01891(5) 0.67682(2) 0.03944(9) Uani 1.00 1 d . . . O(1) O 0.3366(2) 0.3095(5) 0.5734(2) 0.0444(9) Uani 1.00 1 d . . . O(2) O 0.2868(2) 0.6633(5) 0.4350(2) 0.0579(10) Uani 1.00 1 d . . . N(1) N 0.1172(2) 0.4497(6) 0.5209(2) 0.0321(9) Uani 1.00 1 d . . . C(1) C 0.5254(3) 0.2999(6) 0.5723(2) 0.0258(10) Uani 1.00 1 d . . . C(2) C 0.4183(3) 0.3924(6) 0.5402(2) 0.0278(10) Uani 1.00 1 d . . . C(3) C 0.3862(3) 0.5972(6) 0.4633(2) 0.0313(11) Uani 1.00 1 d . . . C(4) C 0.0421(3) 0.3098(6) 0.4553(2) 0.0300(11) Uani 1.00 1 d . . . C(5) C 0.0802(4) 0.1055(7) 0.4060(3) 0.0433(14) Uani 1.00 1 d . . . C(6) C 0.0051(4) -0.0343(9) 0.3412(3) 0.0533(15) Uani 1.00 1 d . . . C(7) C -0.1129(4) 0.0134(10) 0.3202(2) 0.0572(14) Uani 1.00 1 d . . . C(8) C -0.1533(4) 0.2045(8) 0.3657(3) 0.0465(14) Uani 1.00 1 d . . . C(9) C -0.0771(3) 0.3611(7) 0.4344(2) 0.0315(11) Uani 1.00 1 d . . . H(1) H 0.273(5) 0.384(10) 0.549(4) 0.11(2) Uiso 1.00 1 d . . . H(2) H 0.1593 0.0697 0.4201 0.056 Uiso 1.00 1 c R . . H(3) H 0.0317 -0.1683 0.3082 0.067 Uiso 1.00 1 c R . . H(4) H -0.1642 -0.0905 0.2742 0.067 Uiso 1.00 1 c R . . H(5) H -0.2328 0.2352 0.3519 0.054 Uiso 1.00 1 c 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 I(1) 0.0471(2) 0.03623(18) 0.03339(17) 0.00703(16) 0.00932(12) 0.00568(16) O(1) 0.024(2) 0.0590(18) 0.053(2) 0.0047(15) 0.0170(17) 0.0185(15) O(2) 0.0234(19) 0.0757(19) 0.077(2) 0.0184(15) 0.0180(18) 0.0333(17) N(1) 0.0203(18) 0.0399(19) 0.0381(18) 0.0053(14) 0.0117(15) 0.0091(16) C(1) 0.020(2) 0.0243(17) 0.035(2) 0.0014(15) 0.0105(18) 0.0000(16) C(2) 0.020(2) 0.0319(18) 0.034(2) -0.0008(15) 0.0125(19) 0.0010(16) C(3) 0.025(2) 0.032(2) 0.036(2) 0.0068(16) 0.007(2) 0.0015(16) C(4) 0.030(2) 0.031(2) 0.032(2) 0.0046(17) 0.014(2) 0.0112(18) C(5) 0.048(3) 0.041(2) 0.050(2) 0.012(2) 0.029(2) 0.010(2) C(6) 0.085(4) 0.041(2) 0.042(2) 0.005(2) 0.031(2) 0.002(2) C(7) 0.079(3) 0.053(2) 0.037(2) -0.015(2) 0.012(2) -0.002(2) C(8) 0.035(3) 0.055(2) 0.045(2) -0.003(2) 0.005(2) 0.009(2) C(9) 0.028(2) 0.036(2) 0.031(2) -0.0018(17) 0.010(2) 0.0079(18) #============================================================================== _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # 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 I(1) C(1) 2.073(3) yes . . O(1) C(2) 1.317(5) yes . . O(2) C(3) 1.217(4) yes . . N(1) C(4) 1.343(4) yes . . N(1) C(9) 1.339(5) yes . 3_566 C(1) C(2) 1.346(5) yes . . C(1) C(3) 1.443(6) yes . 3_666 C(2) C(3) 1.519(5) yes . . C(4) C(5) 1.424(6) yes . . C(4) C(9) 1.430(5) yes . . C(5) C(6) 1.336(6) yes . . C(6) C(7) 1.413(8) yes . . C(7) C(8) 1.355(7) yes . . C(8) C(9) 1.420(5) yes . . O(1) H(1) 0.85(5) no . . C(5) H(2) 0.950 no . . C(6) H(3) 0.950 no . . C(7) H(4) 0.950 no . . C(8) H(5) 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 C(4) N(1) C(9) 118.1(3) yes . . 3_566 I(1) C(1) C(2) 120.9(3) yes . . . I(1) C(1) C(3) 118.6(2) yes . . 3_666 C(2) C(1) C(3) 120.4(3) yes . . 3_666 O(1) C(2) C(1) 121.9(3) yes . . . O(1) C(2) C(3) 116.9(3) yes . . . C(1) C(2) C(3) 121.2(3) yes . . . O(2) C(3) C(1) 123.9(3) yes . . 3_666 O(2) C(3) C(2) 117.7(4) yes . . . C(1) C(3) C(2) 118.4(3) yes 3_666 . . N(1) C(4) C(5) 120.3(3) yes . . . N(1) C(4) C(9) 120.7(3) yes . . . C(5) C(4) C(9) 118.9(3) yes . . . C(4) C(5) C(6) 120.1(4) yes . . . C(5) C(6) C(7) 121.5(4) yes . . . C(6) C(7) C(8) 120.6(4) yes . . . C(7) C(8) C(9) 120.2(4) yes . . . N(1) C(9) C(4) 121.2(3) yes 3_566 . . N(1) C(9) C(8) 120.1(3) yes 3_566 . . C(4) C(9) C(8) 118.7(3) yes . . . C(2) O(1) H(1) 114(4) no . . . C(4) C(5) H(2) 119.2 no . . . C(6) C(5) H(2) 120.7 no . . . C(5) C(6) H(3) 119.3 no . . . C(7) C(6) H(3) 119.2 no . . . C(6) C(7) H(4) 119.5 no . . . C(8) C(7) H(4) 119.9 no . . . C(7) C(8) H(5) 120.4 no . . . C(9) C(8) H(5) 119.4 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 C(4) N(1) C(9) C(4) 0.4(5) ? . . 3_566 3_566 C(4) N(1) C(9) C(8) -178.8(3) ? . . 3_566 3_566 C(9) N(1) C(4) C(5) -179.7(3) ? 3_566 . . . C(9) N(1) C(4) C(9) -0.4(5) ? 3_566 . . . I(1) C(1) C(2) O(1) -0.0(3) ? . . . . I(1) C(1) C(2) C(3) -179.7(2) ? . . . . I(1) C(1) C(3) O(2) -0.8(4) ? . . 3_666 3_666 I(1) C(1) C(3) C(2) 179.7(2) ? . . 3_666 3_666 C(2) C(1) C(3) O(2) 176.8(3) ? . . 3_666 3_666 C(2) C(1) C(3) C(2) -2.6(5) ? . . 3_666 3_666 C(3) C(1) C(2) O(1) -177.6(3) ? 3_666 . . . C(3) C(1) C(2) C(3) 2.7(5) ? 3_666 . . . O(1) C(2) C(3) O(2) -2.8(5) ? . . . . O(1) C(2) C(3) C(1) 177.7(3) ? . . . 3_666 C(1) C(2) C(3) O(2) 176.9(3) ? . . . . C(1) C(2) C(3) C(1) -2.6(5) ? . . . 3_666 N(1) C(4) C(5) C(6) 179.6(4) ? . . . . N(1) C(4) C(9) N(1) 0.4(6) ? . . . 3_566 N(1) C(4) C(9) C(8) -178.8(3) ? . . . . C(5) C(4) C(9) N(1) 179.7(3) ? . . . 3_566 C(5) C(4) C(9) C(8) 0.5(5) ? . . . . C(9) C(4) C(5) C(6) 0.3(6) ? . . . . C(4) C(5) C(6) C(7) -0.7(7) ? . . . . C(5) C(6) C(7) C(8) 0.2(6) ? . . . . C(6) C(7) C(8) C(9) 0.6(7) ? . . . . C(7) C(8) C(9) N(1) 179.8(4) ? . . . 3_566 C(7) C(8) C(9) C(4) -1.0(6) ? . . . . 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 O(1) N(1) 2.675(4) ? . . O(1) C(4) 3.545(5) ? . . O(1) C(5) 3.580(5) ? . . O(1) C(9) 3.560(5) ? . 3_566 O(2) N(1) 2.967(5) ? . . O(2) C(4) 3.579(5) ? . . O(2) C(5) 3.295(5) ? . 1_565 N(1) O(1) 2.675(4) ? . . N(1) O(2) 2.967(5) ? . . N(1) C(6) 3.582(6) ? . 3_556 N(1) C(7) 3.359(5) ? . 3_556 C(4) O(1) 3.545(5) ? . . C(4) O(2) 3.579(5) ? . . C(4) C(5) 3.589(6) ? . 3_556 C(4) C(6) 3.597(6) ? . 3_556 C(5) O(1) 3.580(5) ? . . C(5) O(2) 3.295(5) ? . 1_545 C(5) C(4) 3.589(6) ? . 3_556 C(5) C(9) 3.376(5) ? . 3_556 C(6) N(1) 3.582(6) ? . 3_556 C(6) C(4) 3.597(6) ? . 3_556 C(7) N(1) 3.359(5) ? . 3_556 C(9) O(1) 3.560(5) ? . 3_566 C(9) C(5) 3.376(5) ? . 3_556 I(1) H(5) 3.289 ? . 4_655 O(1) H(2) 2.948 ? . . O(1) H(5) 3.339 ? . 3_556 O(1) H(5) 2.988 ? . 3_566 O(2) H(2) 3.325 ? . . O(2) H(2) 2.531 ? . 1_565 O(2) H(3) 3.280 ? . 1_565 O(2) H(4) 3.357 ? . 2_555 O(2) H(5) 3.543 ? . 3_566 N(1) H(1) 1.86(6) ? . . N(1) H(2) 3.556 ? . 1_565 N(1) H(4) 3.504 ? . 3_556 C(2) H(2) 3.563 ? . . C(3) H(2) 3.563 ? . 1_565 C(4) H(1) 2.80(5) ? . . C(4) H(3) 3.415 ? . 1_565 C(5) H(1) 3.04(5) ? . . C(5) H(3) 3.353 ? . 2_555 C(5) H(4) 3.549 ? . 2_555 C(6) H(3) 2.851 ? . 2_555 C(7) H(3) 2.916 ? . 2_555 C(8) H(1) 3.03(6) ? . 3_566 C(8) H(2) 3.565 ? . 3_556 C(8) H(3) 3.465 ? . 2_555 C(9) H(1) 2.80(6) ? . 3_566 C(9) H(2) 3.446 ? . 3_556 C(9) H(3) 3.537 ? . 1_565 H(1) N(1) 1.86(6) ? . . H(1) C(4) 2.80(5) ? . . H(1) C(5) 3.04(5) ? . . H(1) C(8) 3.03(6) ? . 3_566 H(1) C(9) 2.80(6) ? . 3_566 H(1) H(2) 2.580 ? . . H(1) H(5) 3.534 ? . 3_556 H(1) H(5) 2.565 ? . 3_566 H(2) O(1) 2.948 ? . . H(2) O(2) 2.531 ? . 1_545 H(2) O(2) 3.325 ? . . H(2) N(1) 3.556 ? . 1_545 H(2) C(2) 3.563 ? . . H(2) C(3) 3.563 ? . 1_545 H(2) C(8) 3.565 ? . 3_556 H(2) C(9) 3.446 ? . 3_556 H(2) H(1) 2.580 ? . . H(2) H(4) 3.432 ? . 2_555 H(3) O(2) 3.280 ? . 1_545 H(3) C(4) 3.415 ? . 1_545 H(3) C(5) 3.353 ? . 2_545 H(3) C(6) 2.851 ? . 2_545 H(3) C(7) 2.916 ? . 2_545 H(3) C(8) 3.465 ? . 2_545 H(3) C(9) 3.537 ? . 1_545 H(3) H(3) 3.027 ? . 2_545 H(3) H(3) 3.027 ? . 2_555 H(3) H(4) 3.140 ? . 2_545 H(4) O(2) 3.357 ? . 2_545 H(4) N(1) 3.504 ? . 3_556 H(4) C(5) 3.549 ? . 2_545 H(4) H(2) 3.432 ? . 2_545 H(4) H(3) 3.140 ? . 2_555 H(5) I(1) 3.289 ? . 4_454 H(5) O(1) 3.339 ? . 3_556 H(5) O(1) 2.988 ? . 3_566 H(5) O(2) 3.543 ? . 3_566 H(5) H(1) 3.534 ? . 3_556 H(5) H(1) 2.565 ? . 3_566 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1) O(2) . . . 2.682(4) 0.85(5) 2.27(6) 110(5) no O(1) H(1) N(1) . . . 2.675(4) 0.85(5) 1.86(6) 159(6) no #============================================================================== # 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 #==============================================================================