Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_General _journal_coden_Cambridge 182 _audit_creation_date 'Thu Jun 14 11:30:23 2001' _audit_creation_method 'by teXsan' _audit_update_record ? #--------------------------------------------------------------------- # SUBMISSION DETAILS loop_ _publ_author_name 'Kitawaki, Yukiko' 'Ono, Noboru' 'Uno, Hidemitsu' _publ_contact_author_name ' Dr. Hidemitsu Uno ' _publ_contact_author_address ; Advanced Instrumentation Center for Chemical Analysis Ehime University Matsuyama 790-8577 Japan ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 81(89927)9663 ' _publ_contact_author_fax ' 81(89927)9663 ' _publ_contact_author_email ' uno@dpc.ehime-u.ac.jp ' _publ_requested_journal ' Chem. Commun' _publ_section_title ; Novel preparation of beta,beta'-connected porphyrin dimers ; #--------------------------------------------------------------------- data_Dipyrroledicarboxylate _database_code_CSD 172085 #--------------------------------------------------------------------- # CHEMICAL DATA _chemical_formula_sum 'C16 H20 N2 O4 ' _chemical_formula_moiety 'C16 H20 N2 O4 ' _chemical_formula_weight 304.35 #--------------------------------------------------------------------- # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 11.134(2) _cell_length_b 7.626(2) _cell_length_c 19.564(2) _cell_angle_alpha 90 _cell_angle_beta 91.266(10) _cell_angle_gamma 90 _cell_volume 1660.8(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.9 _cell_measurement_theta_max 12.7 _cell_measurement_temperature 298.2 #--------------------------------------------------------------------- _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.550 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.210 _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.999 #--------------------------------------------------------------------- # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K¥a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method ¥w _diffrn_reflns_number 4305 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.9997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.9997 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.29 #--------------------------------------------------------------------- # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). 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 3814 _reflns_number_gt 1733 _reflns_threshold_expression F^2^>2.0¥s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.0899 _refine_ls_hydrogen_treatment ; Hydrogens of ethyl groups are calculated. Others are refined isotropically. ; _refine_ls_number_reflns 3811 _refine_ls_number_parameters 240 _refine_ls_goodness_of_fit_ref 1.664 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w == 1/[¥s^2^(Fo^2^) + (0.00200(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.25 _refine_diff_density_min -0.23 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.0118(8) 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 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #--------------------------------------------------------------------- # ATOMIC COORDINATES AND DISPLACEMENT 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.3674(2) 0.2200(3) 0.72566(9) 0.1009(8) Uani 1.00 d . . . O(2) O 0.3884(2) 0.0688(3) 0.62765(9) 0.0934(8) Uani 1.00 d . . . O(3) O 0.1119(2) -0.0024(3) 0.3485(1) 0.1141(9) Uani 1.00 d . . . O(4) O 0.2940(2) -0.0785(3) 0.31125(9) 0.0924(8) Uani 1.00 d . . . N(1) N 0.2957(2) 0.5112(3) 0.6612(1) 0.0715(8) Uani 1.00 d . . . N(2) N 0.3979(2) 0.1110(3) 0.4196(1) 0.0728(9) Uani 1.00 d . . . C(1) C 0.3220(2) 0.3636(3) 0.6247(1) 0.0598(9) Uani 1.00 d . . . C(2) C 0.3015(2) 0.4014(3) 0.5555(1) 0.0587(9) Uani 1.00 d . . . C(3) C 0.2621(2) 0.5782(4) 0.5523(1) 0.0672(9) Uani 1.00 d . . . C(4) C 0.2608(3) 0.6407(4) 0.6175(2) 0.076(1) Uani 1.00 d . . . C(5) C 0.4207(3) 0.2167(4) 0.4736(1) 0.073(1) Uani 1.00 d . . . C(6) C 0.3151(2) 0.2827(3) 0.4972(1) 0.0590(8) Uani 1.00 d . . . C(7) C 0.2222(3) 0.2121(3) 0.4553(1) 0.0640(9) Uani 1.00 d . . . C(8) C 0.2762(3) 0.1065(3) 0.4077(1) 0.0658(10) Uani 1.00 d . . . C(9) C 0.3619(2) 0.2033(4) 0.6571(1) 0.075(1) Uani 1.00 d . . . C(10) C 0.2312(4) 0.6829(5) 0.4893(2) 0.093(1) Uani 1.00 d . . . C(11) C 0.0910(3) 0.2467(6) 0.4642(2) 0.098(2) Uani 1.00 d . . . C(12) C 0.2313(3) 0.0009(4) 0.3511(1) 0.081(1) Uani 1.00 d . . . C(13) C 0.4151(4) 0.0709(6) 0.7637(2) 0.178(2) Uani 1.00 d . . . C(14) C 0.3499(5) 0.0039(5) 0.8084(2) 0.205(2) Uani 1.00 d . . . C(15) C 0.0576(4) -0.1191(6) 0.2979(2) 0.158(2) Uani 1.00 d . . . C(16) C -0.0530(4) -0.1562(8) 0.3127(2) 0.259(3) Uani 1.00 d . . . H(1N) H 0.298(2) 0.513(3) 0.708(1) 0.081(9) Uiso 1.00 calc . . . H(2N) H 0.455(3) 0.054(4) 0.397(2) 0.16(1) Uiso 1.00 calc . . . H(4) H 0.238(2) 0.776(3) 0.637(1) 0.093(8) Uiso 1.00 calc . . . H(5) H 0.506(2) 0.229(3) 0.491(1) 0.082(8) Uiso 1.00 calc . . . H(10a) H 0.229(3) 0.814(4) 0.501(2) 0.18(1) Uiso 1.00 calc . . . H(10b) H 0.289(2) 0.674(3) 0.459(1) 0.09(1) Uiso 1.00 calc . . . H(10c) H 0.159(3) 0.630(4) 0.465(2) 0.18(2) Uiso 1.00 calc . . . H(11a) H 0.074(3) 0.334(4) 0.495(1) 0.14(1) Uiso 1.00 calc . . . H(11b) H 0.049(3) 0.143(4) 0.465(2) 0.14(1) Uiso 1.00 calc . . . H(11c) H 0.057(3) 0.306(5) 0.419(2) 0.20(2) Uiso 1.00 calc . . . H(13a) H 0.4327 -0.0182 0.7316 0.2131 Uiso 1.00 calc . . . H(13b) H 0.4874 0.1081 0.7861 0.2131 Uiso 1.00 calc . . . H(14a) H 0.3289 0.0907 0.8408 0.2459 Uiso 1.00 calc . . . H(14b) H 0.2789 -0.0417 0.7871 0.2459 Uiso 1.00 calc . . . H(14c) H 0.3923 -0.0883 0.8309 0.2459 Uiso 1.00 calc . . . H(15a) H 0.1027 -0.2249 0.2967 0.1893 Uiso 1.00 calc . . . H(15b) H 0.0587 -0.0643 0.2544 0.1893 Uiso 1.00 calc . . . H(16a) H -0.0548 -0.2132 0.3559 0.3107 Uiso 1.00 calc . . . H(16b) H -0.0867 -0.2311 0.2786 0.3107 Uiso 1.00 calc . . . H(16c) H -0.0985 -0.0508 0.3146 0.3107 Uiso 1.00 calc . . . 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 O(1) 0.117(2) 0.127(2) 0.059(1) 0.041(2) 0.001(1) 0.012(1) O(2) 0.112(2) 0.080(1) 0.088(1) 0.035(1) 0.005(1) 0.003(1) O(3) 0.108(2) 0.137(2) 0.098(2) -0.027(2) -0.004(1) -0.038(1) O(4) 0.132(2) 0.081(1) 0.064(1) -0.003(1) 0.009(1) -0.006(1) N(1) 0.080(2) 0.075(2) 0.060(2) 0.005(1) 0.001(1) -0.011(2) N(2) 0.079(2) 0.075(2) 0.064(2) 0.016(2) 0.003(1) -0.002(1) C(1) 0.061(2) 0.059(2) 0.059(2) 0.004(1) 0.000(1) -0.002(2) C(2) 0.056(2) 0.058(2) 0.062(2) -0.001(1) 0.000(1) -0.003(2) C(3) 0.070(2) 0.063(2) 0.070(2) 0.004(2) 0.005(2) 0.005(2) C(4) 0.084(2) 0.065(2) 0.079(2) 0.011(2) 0.003(2) -0.005(2) C(5) 0.073(2) 0.080(2) 0.065(2) 0.014(2) -0.003(2) -0.007(2) C(6) 0.060(2) 0.060(2) 0.056(2) 0.005(2) 0.004(1) 0.002(1) C(7) 0.065(2) 0.066(2) 0.061(2) 0.002(2) 0.005(1) 0.002(2) C(8) 0.085(2) 0.056(2) 0.056(2) -0.001(2) -0.002(2) 0.004(1) C(9) 0.068(2) 0.086(2) 0.070(2) 0.010(2) -0.002(2) 0.005(2) C(10) 0.109(3) 0.084(3) 0.085(3) 0.017(3) 0.012(2) 0.019(2) C(11) 0.072(2) 0.114(4) 0.109(3) -0.003(3) 0.003(2) -0.028(3) C(12) 0.110(3) 0.069(2) 0.065(2) -0.011(2) 0.002(2) 0.012(2) C(13) 0.197(5) 0.245(6) 0.092(3) 0.135(4) 0.026(3) 0.077(3) C(14) 0.291(6) 0.108(3) 0.222(5) 0.059(4) 0.141(4) 0.071(3) C(15) 0.142(4) 0.191(4) 0.139(3) -0.059(4) -0.014(3) -0.060(3) C(16) 0.142(4) 0.410(9) 0.226(5) -0.135(5) 0.040(4) -0.157(5) #--------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #--------------------------------------------------------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(9) 1.347(3) . . yes O(1) C(13) 1.453(4) . . yes O(2) C(9) 1.216(3) . . yes O(3) C(12) 1.329(3) . . yes O(3) C(15) 1.452(4) . . yes O(4) C(12) 1.220(3) . . yes N(1) C(1) 1.368(3) . . yes N(1) C(4) 1.357(3) . . yes N(2) C(5) 1.349(3) . . yes N(2) C(8) 1.371(3) . . yes C(1) C(2) 1.397(3) . . yes C(1) C(9) 1.443(3) . . yes C(2) C(3) 1.419(3) . . yes C(2) C(6) 1.467(3) . . yes C(3) C(4) 1.363(3) . . yes C(3) C(10) 1.502(4) . . yes C(5) C(6) 1.369(3) . . yes C(6) C(7) 1.412(3) . . yes C(7) C(8) 1.379(3) . . yes C(7) C(11) 1.498(4) . . yes C(8) C(12) 1.449(3) . . yes C(13) C(14) 1.257(5) . . yes C(15) C(16) 1.302(5) . . yes #--------------------------------------------------------------------- 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(9) O(1) C(13) 116.4(3) . 1_555 1_555 yes C(12) O(3) C(15) 116.1(3) . 1_555 1_555 yes C(1) N(1) C(4) 109.4(2) . 1_555 1_555 yes C(5) N(2) C(8) 108.5(3) . 1_555 1_555 yes N(1) C(1) C(2) 107.7(2) . 1_555 1_555 yes N(1) C(1) C(9) 122.3(2) . 1_555 1_555 yes C(2) C(1) C(9) 130.0(3) . 1_555 1_555 yes C(1) C(2) C(3) 106.5(2) . 1_555 1_555 yes C(1) C(2) C(6) 127.5(2) . 1_555 1_555 yes C(3) C(2) C(6) 126.0(2) . 1_555 1_555 yes C(2) C(3) C(4) 107.5(3) . 1_555 1_555 yes C(2) C(3) C(10) 127.4(3) . 1_555 1_555 yes C(4) C(3) C(10) 125.1(3) . 1_555 1_555 yes N(1) C(4) C(3) 109.0(3) . 1_555 1_555 yes N(2) C(5) C(6) 109.6(3) . 1_555 1_555 yes C(2) C(6) C(5) 126.4(3) . 1_555 1_555 yes C(2) C(6) C(7) 126.9(2) . 1_555 1_555 yes C(5) C(6) C(7) 106.7(2) . 1_555 1_555 yes C(6) C(7) C(8) 106.9(2) . 1_555 1_555 yes C(6) C(7) C(11) 124.7(3) . 1_555 1_555 yes C(8) C(7) C(11) 128.4(3) . 1_555 1_555 yes N(2) C(8) C(7) 108.3(3) . 1_555 1_555 yes N(2) C(8) C(12) 117.8(3) . 1_555 1_555 yes C(7) C(8) C(12) 133.8(3) . 1_555 1_555 yes O(1) C(9) O(2) 123.1(3) . 1_555 1_555 yes O(1) C(9) C(1) 111.4(3) . 1_555 1_555 yes O(2) C(9) C(1) 125.5(3) . 1_555 1_555 yes O(3) C(12) O(4) 123.5(3) . 1_555 1_555 yes O(3) C(12) C(8) 111.6(3) . 1_555 1_555 yes O(4) C(12) C(8) 124.9(3) . 1_555 1_555 yes O(1) C(13) C(14) 117.7(4) . 1_555 1_555 yes O(3) C(15) C(16) 111.3(4) . 1_555 1_555 yes #--------------------------------------------------------------------- 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 O(1) C(9) C(1) N(1) 0.8(4) 1_555 1_555 1_555 1_555 yes O(1) C(9) C(1) C(2) -178.4(3) 1_555 1_555 1_555 1_555 yes O(2) C(9) O(1) C(13) 4.0(5) 1_555 1_555 1_555 1_555 yes O(2) C(9) C(1) N(1) -178.8(3) 1_555 1_555 1_555 1_555 yes O(2) C(9) C(1) C(2) 2.0(5) 1_555 1_555 1_555 1_555 yes O(3) C(12) C(8) N(2) 175.3(2) 1_555 1_555 1_555 1_555 yes O(3) C(12) C(8) C(7) -5.5(4) 1_555 1_555 1_555 1_555 yes O(4) C(12) O(3) C(15) 4.9(5) 1_555 1_555 1_555 1_555 yes O(4) C(12) C(8) N(2) -3.4(4) 1_555 1_555 1_555 1_555 yes O(4) C(12) C(8) C(7) 175.7(3) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) 0.1(3) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(6) -178.7(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(2) -0.9(3) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(10) -178.9(3) 1_555 1_555 1_555 1_555 yes N(2) C(5) C(6) C(2) 179.4(2) 1_555 1_555 1_555 1_555 yes N(2) C(5) C(6) C(7) 0.4(3) 1_555 1_555 1_555 1_555 yes N(2) C(8) C(7) C(6) 0.0(3) 1_555 1_555 1_555 1_555 yes N(2) C(8) C(7) C(11) -178.6(3) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) 0.9(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 0.5(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(10) 178.4(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(6) C(5) -68.6(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(6) C(7) 110.3(3) 1_555 1_555 1_555 1_555 yes C(1) C(9) O(1) C(13) -175.6(3) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) -0.6(3) 1_555 1_555 1_555 1_555 yes C(2) C(6) C(7) C(8) -179.3(2) 1_555 1_555 1_555 1_555 yes C(2) C(6) C(7) C(11) -0.6(5) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(9) 179.5(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(6) C(5) 112.8(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(6) C(7) -68.3(4) 1_555 1_555 1_555 1_555 yes C(4) N(1) C(1) C(9) 180.0(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(6) 179.3(2) 1_555 1_555 1_555 1_555 yes C(5) N(2) C(8) C(7) 0.2(3) 1_555 1_555 1_555 1_555 yes C(5) N(2) C(8) C(12) 179.6(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) -0.3(3) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(11) 178.5(3) 1_555 1_555 1_555 1_555 yes C(6) C(2) C(1) C(9) 0.6(5) 1_555 1_555 1_555 1_555 yes C(6) C(2) C(3) C(10) -2.8(5) 1_555 1_555 1_555 1_555 yes C(6) C(5) N(2) C(8) -0.4(3) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(8) C(12) -179.2(3) 1_555 1_555 1_555 1_555 yes C(8) C(12) O(3) C(15) -173.9(3) 1_555 1_555 1_555 1_555 yes C(9) O(1) C(13) C(14) -123.1(5) 1_555 1_555 1_555 1_555 yes C(11) C(7) C(8) C(12) 2.2(5) 1_555 1_555 1_555 1_555 yes C(12) O(3) C(15) C(16) 159.7(5) 1_555 1_555 1_555 1_555 yes #--------------------------------------------------------------------- loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) O(4) 3.317(3) . 4_555 ? O(1) C(16) 3.597(5) . 3_556 ? O(2) N(2) 2.914(3) . 3_656 ? O(2) C(4) 3.565(4) . 1_545 ? O(4) N(1) 2.981(3) . 4_554 ? O(4) C(14) 3.304(5) . 4_544 ? O(4) C(13) 3.585(5) . 3_656 ? N(1) C(13) 3.539(5) . 2_656 ? C(9) C(16) 3.521(6) . 3_556 ? #--------------------------------------------------------------------- #End #---------------------------------------------------------------------