#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2005325.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_2005325 loop_ _publ_author_name 'Qi, F.' 'Yu, W.-T.' 'Hong, L.' 'Lin, X.-Y.' 'Yu, Z.-P.' _publ_section_title ; The Charge-Transfer Complex 4-(2-Hydroxyethyl)carbazole--2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (1/1) (HEK--DDQ) ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2274 _journal_page_last 2277 _journal_volume 52 _journal_year 1996 _chemical_formula_iupac 'C14 H13 N O , C8 Cl2 N2 O2' _chemical_formula_moiety 'C14 H13 N O , C8 Cl2 N2 O2' _chemical_formula_sum 'C22 H13 Cl2 N3 O3' _chemical_formula_weight 438.27 _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_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 97.00(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.785(4) _cell_length_b 15.306(7) _cell_length_c 14.573(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 12 _cell_measurement_theta_min 3 _cell_volume 1944.9(13) _computing_cell_refinement 'Nicolet P3 Data-Collection Program' _computing_data_collection 'Nicolet P3 Data-Collection Program (Nicolet, 1985)' _computing_data_reduction 'SHELXTL (Sheldrick, 1985)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution SHELXTL _diffrn_measurement_device 'Nicolet R3m/E' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3931 _diffrn_reflns_theta_max 25 _diffrn_standards_decay_% <5 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.37 _exptl_absorpt_correction_type none _exptl_crystal_colour blue--green _exptl_crystal_density_diffrn 1.50 _exptl_crystal_density_method none _exptl_crystal_description parallelepiped _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.39 _refine_diff_density_min -0.62 _refine_ls_extinction_coef '\c = 0.0007' _refine_ls_extinction_method 'SHELXTL (Sheldrick, 1985)' _refine_ls_goodness_of_fit_obs 1.588 _refine_ls_hydrogen_treatment 'H atoms see text' _refine_ls_number_parameters 285 _refine_ls_number_reflns 2237 _refine_ls_R_factor_obs 0.0614 _refine_ls_shift/esd_max 0.35 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme ' 1/[\s^2^(F)+0.0009F^2^]' _refine_ls_wR_factor_obs 0.0640 _reflns_number_observed 2237 _reflns_number_total 3847 _reflns_observed_criterion F>4\s(F) _[local]_cod_data_source_file bm1017.cif _[local]_cod_data_source_block bm1017a _cod_original_cell_volume 1945.0(10) _cod_database_code 2005325 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 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv Cl1 0.92690(10) 0.70490(10) 0.00410(10) 0.0890(10) Cl2 0.83120(10) 0.51000(10) 0.04350(10) 0.0800(10) O1 0.5358(3) 0.5021(2) 0.1121(2) 0.0580(10) O2 0.6970(4) 0.8310(2) 0.0528(2) 0.0750(10) O3 0.0233(5) 0.0989(3) 0.0654(3) 0.088(2) O3' 0.1701(13) 0.0350(7) 0.0286(6) 0.062(5) N1 0.2790(3) 0.1361(2) 0.2055(2) 0.0410(10) N2 0.2117(4) 0.6108(2) 0.1675(2) 0.0620(10) N3 0.3373(5) 0.8607(2) 0.1369(3) 0.082(2) C1 0.3265(4) 0.2826(2) 0.2046(2) 0.0400(10) C2 0.2917(5) 0.3706(3) 0.2169(3) 0.0510(10) C3 0.1535(5) 0.3912(3) 0.2477(3) 0.062(2) C4 0.0488(5) 0.3262(3) 0.2647(3) 0.058(2) C5 0.0796(4) 0.2398(3) 0.2529(3) 0.0500(10) C6 0.2200(4) 0.2176(2) 0.2228(2) 0.0380(10) C7 0.4524(4) 0.2381(2) 0.1694(2) 0.0380(10) C8 0.4185(4) 0.1482(2) 0.1696(2) 0.0400(10) C9 0.5142(5) 0.0853(3) 0.1387(3) 0.0540(10) C10 0.6485(5) 0.1157(3) 0.1078(3) 0.065(2) C11 0.6861(5) 0.2037(3) 0.1085(3) 0.061(2) C12 0.5905(4) 0.2655(3) 0.1393(3) 0.0520(10) C13 0.1921(5) 0.0546(2) 0.1997(3) 0.0500(10) C14 0.1218(6) 0.0340(3) 0.1038(3) 0.073(2) C15 0.5737(4) 0.5766(2) 0.0983(2) 0.0430(10) C16 0.7198(4) 0.5977(3) 0.0627(3) 0.0510(10) C17 0.7602(4) 0.6798(3) 0.0477(3) 0.0530(10) C18 0.6626(5) 0.7557(3) 0.0667(2) 0.0540(10) C19 0.5160(4) 0.7346(2) 0.1027(2) 0.0450(10) C20 0.4726(4) 0.6508(2) 0.1161(2) 0.0400(10) C21 0.4179(5) 0.8063(2) 0.1208(3) 0.0560(10) C22 0.3290(4) 0.6292(2) 0.1452(2) 0.0440(10) H30 -0.0599 0.1366 0.0422 0.080 H2 0.3622 0.4157 0.2043 0.080 H3 0.1288 0.4513 0.2575 0.080 H4 -0.0469 0.3427 0.2853 0.080 H5 0.0072 0.1955 0.2649 0.080 H9 0.4891 0.0242 0.1385 0.080 H10 0.7174 0.0744 0.0853 0.080 H11 0.7804 0.2218 0.0873 0.080 H12 0.6176 0.3263 0.1400 0.080 H13a 0.2596 0.0080 0.2224 0.080 H13b 0.1108 0.0597 0.2379 0.080 H14a 0.042(5) -0.018(2) 0.104(4) 0.080 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 C6 N1 C8 108.2(3) yes C8 N1 C13 124.5(3) yes C2 C1 C7 133.5(3) yes N1 C6 C1 109.2(3) yes C1 C6 C5 121.1(3) yes C1 C7 C12 134.3(3) yes N1 C8 C7 108.9(3) yes C7 C8 C9 122.7(3) yes O1 C15 C20 120.6(3) yes Cl2 C16 C17 123.2(3) yes Cl1 C17 C18 115.7(3) yes O2 C18 C19 120.7(4) yes C20 C19 C21 120.6(4) yes C15 C20 C22 116.5(3) yes N3 C21 C19 177.3(5) yes C6 N1 C13 125.1(3) yes C2 C1 C6 119.6(3) yes C6 C1 C7 106.7(3) yes N1 C6 C5 129.7(3) yes C1 C7 C8 106.8(3) yes C8 C7 C12 118.9(3) yes N1 C8 C9 128.3(3) yes O1 C15 C16 122.1(3) yes Cl2 C16 C15 115.2(3) yes Cl1 C17 C16 122.0(3) yes O2 C18 C17 123.2(4) yes C18 C19 C21 117.6(3) yes C15 C20 C19 120.8(3) yes C19 C20 C22 122.6(3) yes N2 C22 C20 178.8(4) yes O3' O3 C14 43.9(4) no C1 C2 C3 118.4(4) no C3 C4 C5 121.5(4) no C9 C10 C11 122.2(4) no C7 C12 C11 118.8(4) no O3 C14 O3' 84.1(6) no O3' C14 C13 133.5(7) no O3' C14 H14a 108.(3) no C16 C15 C20 117.3(3) no C16 C17 C18 122.3(4) no C18 C19 C20 121.9(4) no O3 O3' C14 52.0(5) no C2 C3 C4 121.3(4) no C4 C5 C6 118.0(4) no C8 C9 C10 116.3(4) no C10 C11 C12 121.1(4) no N1 C13 C14 112.8(3) no O3 C14 C13 113.1(4) no O3 C14 H14a 99.(2) no C13 C14 H14a 111.(3) no C15 C16 C17 121.6(4) no C17 C18 C19 116.1(4) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O3 C14 1.390(6) yes N1 C8 1.402(5) yes C1 C7 1.445(5) yes Cl1 C17 1.709(4) yes N2 C22 1.151(5) yes C15 C16 1.478(5) yes C17 C18 1.489(6) yes C19 C21 1.440(5) yes O3' C14 1.222(11) yes N1 C13 1.459(5) yes C7 C8 1.409(5) yes Cl2 C16 1.704(4) yes N3 C21 1.136(6) yes C15 C20 1.483(5) yes C18 C19 1.484(6) yes C20 C22 1.418(5) yes N1 C6 1.385(5) yes C1 C6 1.413(5) yes C13 C14 1.492(6) yes O1 C15 1.211(4) yes O2 C18 1.215(5) yes C16 C17 1.331(6) yes C19 C20 1.359(5) yes C1 C2 1.398(5) no C2 C3 1.381(6) no C5 C6 1.400(5) no C8 C9 1.388(6) no C11 C12 1.376(6) no O3 O3' 1.754(12) no C3 C4 1.396(6) no C9 C10 1.393(6) no C14 H14a 1.06(4) no C4 C5 1.366(6) no C7 C12 1.403(5) no C10 C11 1.386(6) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag C19 C1 3.070(10) 4_655 yes C21 C1 3.200(10) 4_655 yes C18 C5 3.260(10) 4_655 yes C19 C7 3.300(10) 4_655 yes C17 C6 3.380(10) 4_655 yes C20 N1 3.190(10) 4_655 yes C20 C8 3.150(10) 4_655 yes C17 C5 3.200(10) 4_655 yes C22 C8 3.290(10) 4_655 yes C18 C1 3.350(10) 4_655 yes C20 C7 3.390(10) 4_655 yes C21 C11 3.360(10) 3_665 yes C18 C6 3.170(10) 4_655 yes C19 C6 3.240(10) 4_655 yes C21 C7 3.300(10) 4_655 yes C22 C9 3.350(10) 4_655 yes C15 N1 3.130(10) 4_655 yes