#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202472.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_2202472 loop_ _publ_author_name 'Zhou, Li-shan' 'Feng, Ya-Qing' 'Bo Gao' 'Da-xin Shi' 'Li, Xiao-Fang' _publ_section_title ; 4,5,6,7-Tetrachloro-2-(1-naphthyl)isoindole-1,3-dione acetone solvate ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1066 _journal_page_last o1067 _journal_paper_doi 10.1107/S1600536803014077 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C18 H7 Cl4 N O2, C3 H6 O' _chemical_formula_moiety 'C18 H7 Cl4 N O2, C3 H6 O' _chemical_formula_sum 'C21 H13 Cl4 N O3' _chemical_formula_weight 469.12 _chemical_name_systematic ; 4,5,6,7-Tetrachloro-2-(naphthalen-1-yl)isoindole-1,3-dione acetone solvate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 94.985(6) _cell_angle_beta 91.165(6) _cell_angle_gamma 114.879(5) _cell_formula_units_Z 2 _cell_length_a 7.706(3) _cell_length_b 9.007(3) _cell_length_c 16.213(6) _cell_measurement_reflns_used 899 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.19 _cell_measurement_theta_min 2.51 _cell_volume 1015.0(6) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 4239 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.51 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.607 _exptl_absorpt_correction_T_max 0.941 _exptl_absorpt_correction_T_min 0.784 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.535 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 476 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.243 _refine_diff_density_min -0.327 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 3567 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0399 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0840P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1050 _reflns_number_gt 2748 _reflns_number_total 3567 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6239.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202472 _cod_database_fobs_code 2202472 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 0.49679(10) 0.76588(8) 0.48951(4) 0.0536(2) Uani d . 1 . . Cl Cl2 0.31412(11) 0.50661(9) 0.61486(4) 0.0544(2) Uani d . 1 . . Cl Cl3 -0.03320(11) 0.17536(9) 0.55758(4) 0.0573(2) Uani d . 1 . . Cl Cl4 -0.19612(10) 0.09529(8) 0.37237(4) 0.0558(2) Uani d . 1 . . Cl O1 0.4191(3) 0.7739(2) 0.30108(11) 0.0549(5) Uani d . 1 . . O O2 -0.0896(3) 0.2890(3) 0.21518(12) 0.0712(6) Uani d . 1 . . O N1 0.1592(3) 0.5473(2) 0.23976(12) 0.0462(5) Uani d . 1 . . N C1 0.2910(4) 0.6421(3) 0.30486(14) 0.0409(6) Uani d . 1 . . C C2 0.2325(3) 0.5428(3) 0.37693(14) 0.0372(5) Uani d . 1 . . C C3 0.3078(3) 0.5805(3) 0.45807(14) 0.0385(6) Uani d . 1 . . C C4 0.2238(4) 0.4645(3) 0.51372(14) 0.0398(6) Uani d . 1 . . C C5 0.0683(4) 0.3147(3) 0.48757(14) 0.0402(6) Uani d . 1 . . C C6 -0.0059(4) 0.2789(3) 0.40504(15) 0.0403(6) Uani d . 1 . . C C7 0.0789(3) 0.3952(3) 0.35112(14) 0.0384(6) Uani d . 1 . . C C8 0.0309(4) 0.3942(3) 0.26106(16) 0.0467(6) Uani d . 1 . . C C9 0.1645(4) 0.6001(3) 0.15810(15) 0.0466(7) Uani d . 1 . . C C10 0.2875(4) 0.5795(4) 0.10489(17) 0.0568(7) Uani d . 1 . . C H10 0.3666 0.5311 0.1208 0.068 Uiso calc R 1 . . H C11 0.2946(5) 0.6322(4) 0.02529(18) 0.0657(9) Uani d . 1 . . C H11 0.3786 0.6183 -0.0117 0.079 Uiso calc R 1 . . H C12 0.1798(5) 0.7029(4) 0.00234(18) 0.0641(9) Uani d . 1 . . C H12 0.1863 0.7371 -0.0505 0.077 Uiso calc R 1 . . H C13 0.0511(4) 0.7259(3) 0.05631(17) 0.0544(7) Uani d . 1 . . C C14 -0.0696(5) 0.8000(4) 0.0337(2) 0.0744(10) Uani d . 1 . . C H14 -0.0657 0.8338 -0.0190 0.089 Uiso calc R 1 . . H C15 -0.1906(6) 0.8227(5) 0.0873(3) 0.0851(11) Uani d . 1 . . C H15 -0.2673 0.8733 0.0713 0.102 Uiso calc R 1 . . H C16 -0.2012(5) 0.7703(5) 0.1665(2) 0.0798(10) Uani d . 1 . . C H16 -0.2851 0.7858 0.2029 0.096 Uiso calc R 1 . . H C17 -0.0882(4) 0.6962(4) 0.19053(19) 0.0626(8) Uani d . 1 . . C H17 -0.0970 0.6613 0.2432 0.075 Uiso calc R 1 . . H C18 0.0402(4) 0.6720(3) 0.13719(16) 0.0474(7) Uani d . 1 . . C O3 0.5994(5) 0.6625(4) 0.7731(2) 0.1259(12) Uani d . 1 . . O C19 0.7113(6) 0.9027(4) 0.7079(2) 0.0831(11) Uani d . 1 . . C H19A 0.7192 0.8318 0.6618 0.125 Uiso calc R 1 . . H H19B 0.8375 0.9845 0.7258 0.125 Uiso calc R 1 . . H H19C 0.6331 0.9557 0.6913 0.125 Uiso calc R 1 . . H C20 0.6253(5) 0.8046(4) 0.7767(2) 0.0684(9) Uani d . 1 . . C C21 0.5669(7) 0.8878(6) 0.8460(3) 0.1204(18) Uani d . 1 . . C H21A 0.4947 0.9419 0.8243 0.181 Uiso calc R 1 . . H H21B 0.6789 0.9676 0.8777 0.181 Uiso calc R 1 . . H H21C 0.4892 0.8078 0.8810 0.181 Uiso calc R 1 . . H 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 Cl1 0.0539(4) 0.0534(4) 0.0449(4) 0.0154(3) -0.0059(3) 0.0018(3) Cl2 0.0648(5) 0.0729(5) 0.0335(4) 0.0364(4) -0.0010(3) 0.0104(3) Cl3 0.0759(5) 0.0582(4) 0.0467(4) 0.0326(4) 0.0164(3) 0.0267(3) Cl4 0.0561(4) 0.0444(4) 0.0555(4) 0.0084(3) 0.0040(3) 0.0152(3) O1 0.0572(12) 0.0448(11) 0.0464(11) 0.0047(10) 0.0012(9) 0.0118(8) O2 0.0739(15) 0.0580(12) 0.0472(12) -0.0058(11) -0.0144(10) 0.0117(9) N1 0.0529(13) 0.0443(12) 0.0331(11) 0.0107(10) -0.0004(9) 0.0144(9) C1 0.0434(15) 0.0431(14) 0.0355(14) 0.0166(12) 0.0025(10) 0.0095(10) C2 0.0391(14) 0.0404(13) 0.0352(13) 0.0189(11) 0.0037(10) 0.0083(10) C3 0.0387(14) 0.0459(14) 0.0354(13) 0.0221(12) 0.0023(10) 0.0056(10) C4 0.0462(15) 0.0522(15) 0.0319(13) 0.0305(13) 0.0032(10) 0.0094(11) C5 0.0480(15) 0.0474(14) 0.0374(14) 0.0293(13) 0.0101(11) 0.0170(11) C6 0.0413(14) 0.0404(13) 0.0435(15) 0.0202(12) 0.0049(11) 0.0099(11) C7 0.0397(14) 0.0418(14) 0.0368(13) 0.0187(12) 0.0040(10) 0.0120(10) C8 0.0499(16) 0.0441(15) 0.0412(15) 0.0137(13) 0.0006(12) 0.0126(12) C9 0.0527(16) 0.0422(14) 0.0324(14) 0.0066(13) -0.0029(11) 0.0119(10) C10 0.0613(19) 0.0579(17) 0.0459(17) 0.0184(15) 0.0046(14) 0.0146(13) C11 0.073(2) 0.068(2) 0.0423(17) 0.0146(17) 0.0138(15) 0.0124(14) C12 0.074(2) 0.0605(18) 0.0366(16) 0.0059(16) -0.0028(14) 0.0185(13) C13 0.0586(18) 0.0445(15) 0.0438(16) 0.0044(13) -0.0084(13) 0.0157(12) C14 0.080(2) 0.064(2) 0.069(2) 0.0171(18) -0.0193(18) 0.0287(17) C15 0.074(3) 0.080(2) 0.104(3) 0.032(2) -0.013(2) 0.030(2) C16 0.066(2) 0.083(2) 0.093(3) 0.033(2) 0.0063(19) 0.017(2) C17 0.060(2) 0.0660(19) 0.0534(18) 0.0169(16) -0.0002(14) 0.0155(14) C18 0.0479(16) 0.0405(14) 0.0390(14) 0.0034(12) -0.0041(12) 0.0105(11) O3 0.171(3) 0.092(2) 0.128(3) 0.064(2) -0.003(2) 0.0416(18) C19 0.099(3) 0.074(2) 0.077(2) 0.036(2) 0.012(2) 0.0149(18) C20 0.067(2) 0.065(2) 0.065(2) 0.0207(17) -0.0143(16) 0.0112(16) C21 0.109(4) 0.122(4) 0.079(3) 0.000(3) 0.024(2) 0.005(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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_publ_flag C1 N1 C8 112.9(2) y C1 N1 C9 122.8(2) y C8 N1 C9 124.2(2) y O1 C1 N1 125.6(2) y O1 C1 C2 129.5(2) y N1 C1 C2 104.9(2) ? C7 C2 C3 121.4(2) ? C7 C2 C1 108.8(2) ? C3 C2 C1 129.8(2) y C2 C3 C4 118.0(2) ? C2 C3 Cl1 120.86(19) ? C4 C3 Cl1 121.14(19) ? C3 C4 C5 120.6(2) ? C3 C4 Cl2 119.3(2) ? C5 C4 Cl2 120.11(18) ? C4 C5 C6 120.5(2) ? C4 C5 Cl3 119.53(18) ? C6 C5 Cl3 119.9(2) ? C7 C6 C5 118.0(2) ? C7 C6 Cl4 121.2(2) ? C5 C6 Cl4 120.83(18) ? C6 C7 C2 121.5(2) ? C6 C7 C8 130.4(2) y C2 C7 C8 108.1(2) ? O2 C8 N1 125.5(2) y O2 C8 C7 129.4(2) y N1 C8 C7 105.1(2) ? C10 C9 C18 122.8(2) ? C10 C9 N1 119.1(3) ? C18 C9 N1 118.2(2) ? C9 C10 C11 119.4(3) ? C9 C10 H10 120.3 ? C11 C10 H10 120.3 ? C12 C11 C10 120.3(3) ? C12 C11 H11 119.9 ? C10 C11 H11 119.9 ? C11 C12 C13 121.6(3) ? C11 C12 H12 119.2 ? C13 C12 H12 119.2 ? C12 C13 C14 122.5(3) ? C12 C13 C18 119.1(3) ? C14 C13 C18 118.4(3) ? C15 C14 C13 121.4(3) ? C15 C14 H14 119.3 ? C13 C14 H14 119.3 ? C14 C15 C16 120.3(4) ? C14 C15 H15 119.8 ? C16 C15 H15 119.8 ? C17 C16 C15 120.2(4) ? C17 C16 H16 119.9 ? C15 C16 H16 119.9 ? C16 C17 C18 121.2(3) ? C16 C17 H17 119.4 ? C18 C17 H17 119.4 ? C17 C18 C9 124.5(2) ? C17 C18 C13 118.6(3) ? C9 C18 C13 116.9(3) ? C20 C19 H19A 109.5 ? C20 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? C20 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? O3 C20 C19 120.0(4) ? O3 C20 C21 123.5(4) ? C19 C20 C21 116.5(3) ? C20 C21 H21A 109.5 ? C20 C21 H21B 109.5 ? H21A C21 H21B 109.5 ? C20 C21 H21C 109.5 ? H21A C21 H21C 109.5 ? H21B C21 H21C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C3 . 1.716(3) y Cl2 C4 . 1.715(2) y Cl3 C5 . 1.713(2) y Cl4 C6 . 1.715(3) y O1 C1 . 1.190(3) y O2 C8 . 1.192(3) y N1 C1 . 1.394(3) y N1 C8 . 1.396(3) y N1 C9 . 1.441(3) y C1 C2 . 1.494(3) ? C2 C7 . 1.379(3) ? C2 C3 . 1.381(3) ? C3 C4 . 1.394(3) ? C4 C5 . 1.398(4) ? C5 C6 . 1.400(3) ? C6 C7 . 1.376(3) ? C7 C8 . 1.497(3) ? C9 C10 . 1.353(4) ? C9 C18 . 1.414(4) ? C10 C11 . 1.407(4) ? C10 H10 . 0.93 ? C11 C12 . 1.352(5) ? C11 H11 . 0.93 ? C12 C13 . 1.403(4) ? C12 H12 . 0.93 ? C13 C14 . 1.412(5) ? C13 C18 . 1.429(4) ? C14 C15 . 1.352(5) ? C14 H14 . 0.93 ? C15 C16 . 1.399(5) ? C15 H15 . 0.93 ? C16 C17 . 1.369(4) ? C16 H16 . 0.93 ? C17 C18 . 1.399(4) ? C17 H17 . 0.93 ? O3 C20 . 1.206(4) y C19 C20 . 1.474(5) y C19 H19A . 0.96 ? C19 H19B . 0.96 ? C19 H19C . 0.96 ? C20 C21 . 1.478(5) y C21 H21A . 0.96 ? C21 H21B . 0.96 ? C21 H21C . 0.96 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C19 H19A Cg1 2_666 0.96 3.21 4.101(4) 156 y C21 H21B Cg2 2_676 0.96 3.12 3.831(5) 132 y C21 H21B Cg3 2_676 0.96 3.05 3.913(6) 151 y 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 C8 N1 C1 O1 176.8(3) ? C9 N1 C1 O1 0.3(4) ? C8 N1 C1 C2 -3.8(3) ? C9 N1 C1 C2 179.6(2) ? O1 C1 C2 C7 -178.1(3) ? N1 C1 C2 C7 2.6(3) ? O1 C1 C2 C3 2.3(5) ? N1 C1 C2 C3 -177.0(2) ? C7 C2 C3 C4 0.0(3) ? C1 C2 C3 C4 179.5(2) ? C7 C2 C3 Cl1 -179.10(19) ? C1 C2 C3 Cl1 0.4(4) ? C2 C3 C4 C5 0.2(3) ? Cl1 C3 C4 C5 179.21(18) ? C2 C3 C4 Cl2 179.71(18) ? Cl1 C3 C4 Cl2 -1.2(3) ? C3 C4 C5 C6 -0.2(4) ? Cl2 C4 C5 C6 -179.71(19) ? C3 C4 C5 Cl3 -179.45(18) ? Cl2 C4 C5 Cl3 1.0(3) ? C4 C5 C6 C7 0.0(4) ? Cl3 C5 C6 C7 179.33(19) ? C4 C5 C6 Cl4 179.82(19) ? Cl3 C5 C6 Cl4 -0.9(3) ? C5 C6 C7 C2 0.1(4) ? Cl4 C6 C7 C2 -179.70(19) ? C5 C6 C7 C8 -178.9(2) ? Cl4 C6 C7 C8 1.4(4) ? C3 C2 C7 C6 -0.1(4) ? C1 C2 C7 C6 -179.7(2) ? C3 C2 C7 C8 179.1(2) ? C1 C2 C7 C8 -0.5(3) ? C1 N1 C8 O2 -176.8(3) ? C9 N1 C8 O2 -0.2(5) ? C1 N1 C8 C7 3.5(3) ? C9 N1 C8 C7 -179.9(2) ? C6 C7 C8 O2 -2.4(5) ? C2 C7 C8 O2 178.6(3) ? C6 C7 C8 N1 177.3(3) ? C2 C7 C8 N1 -1.7(3) ? C1 N1 C9 C10 81.4(3) y C8 N1 C9 C10 -94.8(3) y C1 N1 C9 C18 -98.4(3) y C8 N1 C9 C18 85.5(3) y C18 C9 C10 C11 0.4(4) ? N1 C9 C10 C11 -179.4(2) ? C9 C10 C11 C12 0.1(4) ? C10 C11 C12 C13 -0.1(5) ? C11 C12 C13 C14 179.8(3) ? C11 C12 C13 C18 -0.5(4) ? C12 C13 C14 C15 -179.1(3) ? C18 C13 C14 C15 1.1(5) ? C13 C14 C15 C16 -1.0(6) ? C14 C15 C16 C17 0.3(6) ? C15 C16 C17 C18 0.4(5) ? C16 C17 C18 C9 178.5(3) ? C16 C17 C18 C13 -0.2(4) ? C10 C9 C18 C17 -179.6(3) ? N1 C9 C18 C17 0.1(4) ? C10 C9 C18 C13 -0.9(4) ? N1 C9 C18 C13 178.9(2) ? C12 C13 C18 C17 179.8(3) ? C14 C13 C18 C17 -0.5(4) ? C12 C13 C18 C9 0.9(4) ? C14 C13 C18 C9 -179.3(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131678