#------------------------------------------------------------------------------ #$Date: 2014-07-12 07:06:18 +0300 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/20/7112099.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7112099 loop_ _publ_author_name 'Li Qiu' 'Xuhui Zhuang' 'Na Zhao' 'Xiao Wang' 'Zengjian An' 'Zhenggang Lan' 'Xiaobo Wan' _publ_section_title ; Benzo[f]benzo[5,6]indolo[3,2-b]indole: a stable unsubstituted 4npi-electron acene with an antiaromatic 1,4-diazapentalene core ; _journal_name_full Chem.Commun. _journal_page_first 3324 _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C14 H8 N2' _chemical_formula_sum 'C14 H8 N2' _chemical_formula_weight 204.22 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 98.578(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.149(2) _cell_length_b 4.8716(16) _cell_length_c 14.555(5) _cell_measurement_reflns_used 847 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.15 _cell_measurement_theta_min 2.83 _cell_volume 501.2(3) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.962 _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0250 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3106 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.83 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_correction_T_min 0.9822 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2000)' _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.651 _refine_diff_density_min -0.127 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 73 _refine_ls_number_reflns 852 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0618 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0988P)^2^+0.2501P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1603 _refine_ls_wR_factor_ref 0.1786 _reflns_number_gt 605 _reflns_number_total 852 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c3cc49418g2.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P2(1)/c ' _[local]_cod_cif_authors_sg_Hall '-P 2ybc ' _cod_original_cell_volume 501.3(3) _cod_database_code 7112099 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 C1 C 0.0452(4) 0.1975(5) 0.10005(18) 0.0472(7) Uani 1 1 d . C2 C 0.0731(4) -0.0014(6) 0.16558(19) 0.0577(8) Uani 1 1 d . H2 H -0.0269 -0.0650 0.1939 0.069 Uiso 1 1 calc R C3 C 0.2537(4) -0.1087(6) 0.1898(2) 0.0608(9) Uani 1 1 d . H3 H 0.2747 -0.2442 0.2352 0.073 Uiso 1 1 calc R C4 C 0.4009(4) -0.0182(6) 0.1479(2) 0.0578(8) Uani 1 1 d . H4 H 0.5204 -0.0943 0.1649 0.069 Uiso 1 1 calc R C5 C 0.3752(4) 0.1879(6) 0.0796(2) 0.0537(8) Uani 1 1 d . H5 H 0.4757 0.2503 0.0515 0.064 Uiso 1 1 calc R C6 C 0.1951(4) 0.2946(5) 0.05572(18) 0.0472(7) Uani 1 1 d U C7 C 0.0971(4) 0.5056(5) -0.00849(18) 0.0468(7) Uani 1 1 d U N1 N -0.1378(3) 0.3264(5) 0.06923(17) 0.0557(8) Uani 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0509(15) 0.0439(14) 0.0447(15) -0.0098(11) 0.0000(11) 0.0028(11) C2 0.0677(18) 0.0513(16) 0.0544(17) -0.0028(14) 0.0096(13) -0.0017(14) C3 0.073(2) 0.0497(16) 0.0549(17) 0.0042(13) -0.0074(14) 0.0020(15) C4 0.0514(16) 0.0489(16) 0.0671(19) -0.0054(13) -0.0105(13) 0.0067(13) C5 0.0522(16) 0.0463(16) 0.0624(18) -0.0070(13) 0.0084(13) -0.0062(12) C6 0.0587(16) 0.0352(13) 0.0456(15) -0.0077(10) 0.0005(11) -0.0017(11) C7 0.0524(15) 0.0431(13) 0.0468(14) -0.0073(11) 0.0136(10) -0.0089(11) N1 0.0568(15) 0.0521(15) 0.0603(15) 0.0012(11) 0.0154(11) -0.0022(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C2 C1 C6 121.3(3) . . C2 C1 N1 123.7(3) . . C6 C1 N1 115.0(2) . . C1 C2 C3 118.8(3) . . C1 C2 H2 120.6 . . C3 C2 H2 120.6 . . C4 C3 C2 121.0(3) . . C4 C3 H3 119.5 . . C2 C3 H3 119.5 . . C3 C4 C5 121.2(3) . . C3 C4 H4 119.4 . . C5 C4 H4 119.4 . . C6 C5 C4 117.7(3) . . C6 C5 H5 121.1 . . C4 C5 H5 121.1 . . C5 C6 C1 120.0(3) . . C5 C6 C7 138.5(3) . . C1 C6 C7 101.5(2) . . N1 C7 C7 117.9(3) 3_565 3_565 N1 C7 C6 138.2(3) 3_565 . C7 C7 C6 103.9(3) 3_565 . C7 N1 C1 101.7(2) 3_565 . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C2 1.353(4) . C1 C6 1.412(4) . C1 N1 1.460(3) . C2 C3 1.389(4) . C2 H2 0.9300 . C3 C4 1.366(5) . C3 H3 0.9300 . C4 C5 1.405(4) . C4 H4 0.9300 . C5 C6 1.384(4) . C5 H5 0.9300 . C6 C7 1.492(4) . C7 N1 1.270(4) 3_565 C7 C7 1.447(5) 3_565 N1 C7 1.270(4) 3_565 _journal_paper_doi 10.1039/c3cc49418g