#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/80/2008099.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2008099 loop_ _publ_author_name 'Shinya Matsumoto' 'Keiji Matsuhama' 'Jin Mizuguchi' _publ_contact_author ; Prof. Jin Mizuguchi Department of Applied Physics Faculty of Engineering Yokohama National University 79-5 Tokiwadai, Hodogaya-ku 240-8501 Yokohama, Japan ; _publ_section_title ; \b Metal-free phthalocyanine ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 131 _journal_page_last 133 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C32 H18 N8' _chemical_formula_sum 'C32 H18 N8' _chemical_formula_weight 514.55 _chemical_name_systematic '\b phthalocyanine' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _audit_creation_method 'from TEXRAY.INF file' _cell_angle_alpha 90 _cell_angle_beta 121.98(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 19.870(7) _cell_length_b 4.731(7) _cell_length_c 14.813(7) _cell_measurement_reflns_used 20 _cell_measurement_temperature 296.2 _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 14.5 _cell_volume 1181(2) _computing_cell_refinement 'Rigaku/AFC Diffractometer Control' _computing_data_collection 'Rigaku/AFC Diffractometer Control' _computing_data_reduction 'teXsan (Molecular Science Corporation, 1995)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 296.2 _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.077 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 3149 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.80 _diffrn_standards_decay_% -0.94 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ' (North et al., 1968)' _exptl_crystal_colour 'dark blue' _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_meas 1.443 _exptl_crystal_description prism _exptl_crystal_F_000 532.00 _exptl_crystal_size_max 0.800 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.21 _refine_diff_density_min -0.16 _refine_ls_extinction_coef 0.007(4) _refine_ls_extinction_method ; Zachariasen (1967) type 2 Gaussian isotropic ; _refine_ls_goodness_of_fit_all 1.124 _refine_ls_goodness_of_fit_obs 1.182 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 185 _refine_ls_number_reflns 1868 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_obs 0.0552 _refine_ls_shift/esd_max 0.0080 _refine_ls_shift/esd_mean 0.0000 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00099|Fo|^2^]' _refine_ls_wR_factor_all 0.0688 _refine_ls_wR_factor_obs 0.0592 _reflns_number_observed 1868 _reflns_number_total 3037 _reflns_observed_criterion >sigma(I) _[local]_cod_data_source_file oa1066.cif _[local]_cod_data_source_block MfPc _[local]_cod_cif_authors_sg_H-M 'P 21/a' _cod_original_cell_volume 1181.0(10) _cod_database_code 2008099 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,-z -x,-y,-z 1/2+x,1/2-y,z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy N1 -0.03440(10) 0.3077(4) -0.13450(10) 0.0337(5) Uani d . . 1.00 N2 0.07930(10) -0.0012(4) -0.07350(10) 0.0352(5) Uani d . . 1.00 N3 0.09990(10) 0.2818(4) 0.07610(10) 0.0337(5) Uani d . . 1.00 N4 0.16180(10) 0.4727(4) 0.25460(10) 0.0342(5) Uani d . . 1.00 C1 -0.10280(10) 0.3507(5) -0.2319(2) 0.0325(5) Uani d . . 1.00 C2 -0.10320(10) 0.1657(5) -0.3112(2) 0.0339(5) Uani d . . 1.00 C3 -0.15630(10) 0.1274(6) -0.4191(2) 0.0421(6) Uani d . . 1.00 C4 -0.1369(2) -0.0690(6) -0.4711(2) 0.0469(7) Uani d . . 1.00 C5 -0.0665(2) -0.2228(6) -0.4172(2) 0.0482(7) Uani d . . 1.00 C6 -0.01290(10) -0.1855(5) -0.3091(2) 0.0411(6) Uani d . . 1.00 C7 -0.03270(10) 0.0118(5) -0.2573(2) 0.0343(5) Uani d . . 1.00 C8 0.00920(10) 0.1041(5) -0.1465(2) 0.0327(5) Uani d . . 1.00 C9 0.11970(10) 0.0829(5) 0.0270(2) 0.0320(5) Uani d . . 1.00 C10 0.19740(10) -0.0285(5) 0.1051(2) 0.0334(5) Uani d . . 1.00 C11 0.24450(10) -0.2299(5) 0.0958(2) 0.0407(6) Uani d . . 1.00 C12 0.31740(10) -0.2883(6) 0.1857(2) 0.0459(7) Uani d . . 1.00 C13 0.34250(10) -0.1515(6) 0.2822(2) 0.0465(7) Uani d . . 1.00 C14 0.29580(10) 0.0477(5) 0.2916(2) 0.0409(6) Uani d . . 1.00 C15 0.22250(10) 0.1088(5) 0.2015(2) 0.0339(5) Uani d . . 1.00 C16 0.15970(10) 0.3046(5) 0.1815(2) 0.0323(5) Uani d . . 1.00 H3 -0.2044 0.2317 -0.4561 0.0505 Uiso calc . . 1.00 H3N 0.055(2) 0.393(6) 0.047(2) 0.0628 Uiso calc . . 1.00 H4 -0.1723 -0.0991 -0.5453 0.0563 Uiso calc . . 1.00 H5 -0.0550 -0.3562 -0.4552 0.0578 Uiso calc . . 1.00 H6 0.0352 -0.2898 -0.2721 0.0493 Uiso calc . . 1.00 H11 0.2272 -0.3233 0.0303 0.0488 Uiso calc . . 1.00 H12 0.3512 -0.4238 0.1819 0.0551 Uiso calc . . 1.00 H13 0.3929 -0.1968 0.3428 0.0558 Uiso calc . . 1.00 H14 0.3132 0.1397 0.3574 0.0490 Uiso calc . . 1.00 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 N1 0.0330(9) 0.0353(9) 0.0329(9) 0.0011(8) 0.0174(8) -0.0003(8) N2 0.0353(9) 0.0387(10) 0.0346(9) 0.0011(8) 0.0206(8) -0.0027(8) N3 0.0337(9) 0.0346(10) 0.0329(9) 0.0031(8) 0.0177(8) -0.0006(8) N4 0.0346(9) 0.0367(10) 0.0311(9) -0.0003(8) 0.0174(8) 0.0001(8) C1 0.0340(10) 0.0340(10) 0.0317(10) -0.0022(9) 0.0187(9) -0.0012(8) C2 0.0380(10) 0.0320(10) 0.0350(10) -0.0037(9) 0.0213(9) -0.0043(9) C3 0.0420(10) 0.0460(10) 0.0330(10) -0.0010(10) 0.0160(10) -0.0020(10) C4 0.0520(10) 0.052(2) 0.0310(10) -0.0060(10) 0.0180(10) -0.0100(10) C5 0.055(2) 0.0510(10) 0.0430(10) -0.0050(10) 0.0290(10) -0.0170(10) C6 0.0430(10) 0.0420(10) 0.0410(10) 0.0000(10) 0.0240(10) -0.0090(10) C7 0.0360(10) 0.0360(10) 0.0330(10) -0.0061(9) 0.0195(9) -0.0052(9) C8 0.0350(10) 0.0330(10) 0.0340(10) -0.0041(9) 0.0209(9) -0.0038(9) C9 0.0350(10) 0.0330(10) 0.0330(10) 0.0018(9) 0.0209(9) 0.0026(8) C10 0.0370(10) 0.0350(10) 0.0340(10) 0.0031(9) 0.0216(9) 0.0068(9) C11 0.0440(10) 0.0430(10) 0.0440(10) 0.0080(10) 0.0290(10) 0.0038(10) C12 0.0430(10) 0.0520(10) 0.0530(10) 0.0180(10) 0.0330(10) 0.0150(10) C13 0.0360(10) 0.057(2) 0.0440(10) 0.0110(10) 0.0190(10) 0.0160(10) C14 0.0400(10) 0.0440(10) 0.0360(10) 0.0040(10) 0.0180(10) 0.0060(10) C15 0.0360(10) 0.0330(10) 0.0350(10) 0.0022(10) 0.0206(9) 0.0062(9) C16 0.0330(10) 0.0340(10) 0.0296(10) -0.0003(9) 0.0159(9) 0.0032(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 1_555 1_555 1.376(3) no N1 C8 1_555 1_555 1.369(3) no N2 C8 1_555 1_555 1.327(3) no N2 C9 1_555 1_555 1.324(3) no N3 C9 1_555 1_555 1.368(3) no N3 C16 1_555 1_555 1.376(3) no N3 H3N 1_555 1_555 0.92(3) no N4 C1 1_555 3_565 1.330(3) no N4 C16 1_555 1_555 1.327(3) no C1 C2 1_555 1_555 1.462(3) no C2 C3 1_555 1_555 1.383(3) yes C2 C7 1_555 1_555 1.395(3) yes C3 C4 1_555 1_555 1.387(3) yes C3 H3 1_555 1_555 0.950 no C4 C5 1_555 1_555 1.392(4) yes C4 H4 1_555 1_555 0.950 no C5 C6 1_555 1_555 1.387(3) yes C5 H5 1_555 1_555 0.950 no C6 C7 1_555 1_555 1.391(3) yes C6 H6 1_555 1_555 0.950 no C7 C8 1_555 1_555 1.459(3) no C9 C10 1_555 1_555 1.452(3) no C10 C11 1_555 1_555 1.392(3) yes C10 C15 1_555 1_555 1.399(3) yes C11 C12 1_555 1_555 1.380(3) yes C11 H11 1_555 1_555 0.950 no C12 C13 1_555 1_555 1.399(4) yes C12 H12 1_555 1_555 0.950 no C13 C14 1_555 1_555 1.380(3) yes C13 H13 1_555 1_555 0.950 no C14 C15 1_555 1_555 1.389(3) yes C14 H14 1_555 1_555 0.950 no C15 C16 1_555 1_555 1.452(3) no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 1 0 0 2 4 0 -1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N1 C8 1_555 1_555 1_555 108.0(2) no C8 N2 C9 1_555 1_555 1_555 123.6(2) no C9 N3 C16 1_555 1_555 1_555 109.7(2) no C9 N3 H3N 1_555 1_555 1_555 128.0(10) no C16 N3 H3N 1_555 1_555 1_555 122.0(10) no C1 N4 C16 3_565 1_555 1_555 121.9(2) no N1 C1 N4 1_555 1_555 3_565 127.4(2) no N1 C1 C2 1_555 1_555 1_555 109.6(2) no N4 C1 C2 3_565 1_555 1_555 123.0(2) no C1 C2 C3 1_555 1_555 1_555 133.0(2) no C1 C2 C7 1_555 1_555 1_555 106.0(2) no C3 C2 C7 1_555 1_555 1_555 120.9(2) yes C2 C3 C4 1_555 1_555 1_555 117.6(2) yes C2 C3 H3 1_555 1_555 1_555 121.2(2) no C4 C3 H3 1_555 1_555 1_555 121.2(2) no C3 C4 C5 1_555 1_555 1_555 121.4(2) yes C3 C4 H4 1_555 1_555 1_555 119.3(3) no C5 C4 H4 1_555 1_555 1_555 119.3(2) no C4 C5 C6 1_555 1_555 1_555 121.3(2) yes C4 C5 H5 1_555 1_555 1_555 119.3(2) no C6 C5 H5 1_555 1_555 1_555 119.3(3) no C5 C6 C7 1_555 1_555 1_555 117.0(2) yes C5 C6 H6 1_555 1_555 1_555 121.5(2) no C7 C6 H6 1_555 1_555 1_555 121.5(2) no C2 C7 C6 1_555 1_555 1_555 121.7(2) yes C2 C7 C8 1_555 1_555 1_555 106.9(2) no C6 C7 C8 1_555 1_555 1_555 131.4(2) no N1 C8 N2 1_555 1_555 1_555 128.4(2) no N1 C8 C7 1_555 1_555 1_555 109.5(2) no N2 C8 C7 1_555 1_555 1_555 122.2(2) no N2 C9 N3 1_555 1_555 1_555 129.1(2) no N2 C9 C10 1_555 1_555 1_555 122.8(2) no N3 C9 C10 1_555 1_555 1_555 108.1(2) no C9 C10 C11 1_555 1_555 1_555 131.1(2) no C9 C10 C15 1_555 1_555 1_555 107.3(2) no C11 C10 C15 1_555 1_555 1_555 121.6(2) yes C10 C11 C12 1_555 1_555 1_555 117.4(2) yes C10 C11 H11 1_555 1_555 1_555 121.3(2) no C12 C11 H11 1_555 1_555 1_555 121.3(2) no C11 C12 C13 1_555 1_555 1_555 121.1(2) yes C11 C12 H12 1_555 1_555 1_555 119.4(3) no C13 C12 H12 1_555 1_555 1_555 119.5(2) no C12 C13 C14 1_555 1_555 1_555 121.6(2) yes C12 C13 H13 1_555 1_555 1_555 119.2(3) no C14 C13 H13 1_555 1_555 1_555 119.2(3) no C13 C14 C15 1_555 1_555 1_555 117.7(2) yes C13 C14 H14 1_555 1_555 1_555 121.2(2) no C15 C14 H14 1_555 1_555 1_555 121.2(2) no C10 C15 C14 1_555 1_555 1_555 120.6(2) yes C10 C15 C16 1_555 1_555 1_555 106.6(2) no C14 C15 C16 1_555 1_555 1_555 132.8(2) no N3 C16 N4 1_555 1_555 1_555 127.4(2) no N3 C16 C15 1_555 1_555 1_555 108.3(2) no N4 C16 C15 1_555 1_555 1_555 124.3(2) no 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 N1 N3 3.378(3) 1_555 3_555 no N1 C9 3.417(3) 1_555 3_555 no N2 C12 3.405(3) 1_555 2_555 no N2 H3N 3.45(3) 1_555 3_555 no N2 H3N 3.53(3) 1_555 1_545 no N3 C8 3.394(3) 1_555 3_555 no N3 C11 3.577(3) 1_555 1_565 no N4 C7 3.456(3) 1_555 3_555 no N4 C15 3.483(3) 1_555 1_565 no N4 C2 3.495(3) 1_555 3_555 no N4 C10 3.555(3) 1_555 1_565 no C1 C6 3.388(3) 1_555 1_565 no C1 C15 3.422(3) 1_555 3_555 no C1 C16 3.513(3) 1_555 3_555 no C1 C7 3.524(3) 1_555 1_565 no C2 C16 3.492(3) 1_555 3_555 no C2 C5 3.546(4) 1_555 1_565 no C2 C6 3.547(3) 1_555 1_565 no C3 C5 3.547(4) 1_555 1_565 no C7 C16 3.588(3) 1_555 3_555 no C8 H3N 3.37(3) 1_555 3_555 no C9 H3N 3.57(3) 1_555 1_545 no C10 C16 3.563(3) 1_555 1_545 no C11 C16 3.401(3) 1_555 1_545 no C12 C15 3.496(3) 1_555 1_545 no