#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104975.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_2104975 loop_ _publ_author_name 'Solanko, Katarzyna A.' 'Bond, Andrew D.' _publ_section_title ; Intermolecular interactions and unexpected isostructurality in the crystal structures of the dichlorobenzaldehyde isomers ; _journal_coeditor_code GP5044 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 437 _journal_page_last 445 _journal_paper_doi 10.1107/S0108768111035786 _journal_volume 67 _journal_year 2011 _chemical_formula_moiety 'C7 H4 Cl2 O' _chemical_formula_sum 'C7 H4 Cl2 O' _chemical_formula_weight 175.00 _chemical_name_common 2,5-dichlorobenzaldehyde _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 89.091(5) _cell_angle_beta 85.728(5) _cell_angle_gamma 81.115(5) _cell_formula_units_Z 3 _cell_length_a 3.8150(5) _cell_length_b 7.8290(11) _cell_length_c 17.895(3) _cell_measurement_reflns_used 1343 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 24.12 _cell_measurement_theta_min 2.87 _cell_volume 526.60(13) _computing_cell_refinement 'SAINT v.7.06a (Bruker, 2003)' _computing_data_collection 'APEX2 v.1.0-22 (Bruker Nonius, 2004)' _computing_data_reduction 'SAINT v.7.06a' _computing_molecular_graphics 'SHELXTL v.6.10' _computing_publication_material 'SHELXTL v.6.10' _computing_structure_refinement 'SHELXTL v.6.10' _computing_structure_solution 'SHELXTL v.6.10 (Sheldrick, 2000)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_device_type 'Bruker-Nonius X8APEX-II CCD' _diffrn_measurement_method 'thin-slice \w and \f scans' _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 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 6319 _diffrn_reflns_theta_full 25.12 _diffrn_reflns_theta_max 25.12 _diffrn_reflns_theta_min 4.31 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.838 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_correction_T_min 0.704 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.721852 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.411 _refine_diff_density_min -0.299 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 1827 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0631 _refine_ls_R_factor_gt 0.0367 _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^)+(0.0339P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.0806 _reflns_number_gt 1313 _reflns_number_total 1827 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 3 in P-1 CELL 0.71073 3.8150 7.8290 17.895 89.091 85.728 81.115 ZERR 3.00 0.0005 0.0011 0.003 0.005 0.005 0.005 LATT 1 SFAC C H O CL UNIT 21 12 3 6 SIZE 0.35 0.03 0.03 TEMP -153 L.S. 20 ACTA BOND $H CONF LIST 4 FMAP 2 PLAN -5 SHEL 5.8 0 WGHT 0.033900 FVAR 0.80178 O1 3 0.20547 1.23105 0.18353 11.00000 0.04155 0.01720 = 0.02617 -0.00147 0.00224 -0.01133 C1 1 0.02816 0.95390 0.18013 11.00000 0.01651 0.01392 = 0.01680 0.00285 -0.00315 -0.00063 C2 1 -0.11456 0.82126 0.21890 11.00000 0.01068 0.02360 = 0.01393 0.00439 -0.00341 -0.00062 CL2 4 -0.30351 0.85462 0.31062 11.00000 0.02618 0.03168 = 0.01869 0.00427 0.00222 -0.00705 C3 1 -0.10855 0.66061 0.18701 11.00000 0.01607 0.01523 = 0.02437 0.00820 -0.00362 -0.00446 AFIX 43 H3 2 -0.20034 0.57102 0.21490 11.00000 -1.20000 AFIX 0 C4 1 0.03170 0.63272 0.11464 11.00000 0.01957 0.01228 = 0.02649 0.00040 -0.00736 -0.00414 AFIX 43 H4 2 0.03473 0.52356 0.09195 11.00000 -1.20000 AFIX 0 C5 1 0.16855 0.76275 0.07462 11.00000 0.01208 0.01419 = 0.01559 0.00101 -0.00206 -0.00061 CL5 4 0.34316 0.72875 -0.01745 11.00000 0.02439 0.01670 = 0.01794 -0.00008 0.00028 -0.00440 C6 1 0.16832 0.92113 0.10660 11.00000 0.01335 0.01635 = 0.02058 0.00695 -0.00378 -0.00273 AFIX 43 H6 2 0.26442 1.00909 0.07841 11.00000 -1.20000 AFIX 0 C7 1 0.04268 1.12403 0.21324 11.00000 0.02258 0.01713 = 0.02356 0.00070 -0.00217 0.00141 AFIX 43 H7 2 -0.08267 1.15106 0.26048 11.00000 -1.20000 AFIX 0 PART 1 O1A 3 0.08146 0.94568 0.51138 10.50000 0.05635 0.01726 = 0.05590 -0.00313 -0.01771 0.01244 C7A 1 0.25940 0.83830 0.54778 10.50000 0.03720 0.01553 = 0.02887 -0.00315 0.00228 -0.00522 AFIX 43 H7A 2 0.31689 0.87238 0.59553 10.50000 -1.20000 AFIX 3 PART 2 H4A 2 0.31416 0.78266 0.54332 10.50000 -1.20000 AFIX 0 PART 0 C1A 1 0.38778 0.66811 0.52553 11.00000 0.01686 0.01930 = 0.02619 0.00467 0.00346 -0.00538 C2A 1 0.57525 0.54224 0.57071 11.00000 0.01521 0.02543 = 0.02229 0.00649 0.00322 -0.00658 CL2A 4 0.66967 0.59588 0.66033 11.00000 0.02446 0.03872 = 0.02178 0.00416 -0.00223 -0.00740 C3A 1 0.68590 0.37756 0.54496 11.00000 0.01477 0.02507 = 0.02320 0.01133 0.00259 -0.00207 AFIX 43 H3A 2 0.81435 0.29427 0.57591 11.00000 -1.20000 AFIX 0 HKLF 4 END ; _cod_data_source_file gp5044.cif _cod_data_source_block 3 _cod_database_code 2104975 _cod_database_fobs_code 2104975 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _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_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.2055(5) 1.2310(2) 0.18353(11) 0.0278(5) Uani d . 1 1 . . C C1 0.0282(7) 0.9539(3) 0.18013(16) 0.0159(7) Uani d . 1 1 . . C C2 -0.1146(7) 0.8213(4) 0.21890(16) 0.0162(7) Uani d . 1 1 . . Cl Cl2 -0.30351(19) 0.85462(10) 0.31062(4) 0.0255(2) Uani d . 1 1 . . C C3 -0.1086(7) 0.6606(3) 0.18701(17) 0.0183(7) Uani d . 1 1 . . H H3 -0.2003 0.5710 0.2149 0.022 Uiso calc R 1 1 . . C C4 0.0317(7) 0.6327(4) 0.11464(17) 0.0190(7) Uani d . 1 1 . . H H4 0.0347 0.5236 0.0920 0.023 Uiso calc R 1 1 . . C C5 0.1685(7) 0.7627(3) 0.07462(15) 0.0141(7) Uani d . 1 1 . . Cl Cl5 0.34316(19) 0.72875(9) -0.01745(4) 0.0196(2) Uani d . 1 1 . . C C6 0.1683(7) 0.9211(4) 0.10660(16) 0.0167(7) Uani d . 1 1 . . H H6 0.2644 1.0091 0.0784 0.020 Uiso calc R 1 1 . . C C7 0.0427(8) 1.1240(4) 0.21324(17) 0.0215(7) Uani d . 1 1 . . H H7 -0.0827 1.1511 0.2605 0.026 Uiso calc R 1 1 . . O O1A 0.0815(13) 0.9457(5) 0.5114(3) 0.0444(13) Uani d P 0.50 1 . 1 C C7A 0.2594(15) 0.8383(8) 0.5478(3) 0.0272(16) Uani d P 0.50 1 A 1 H H7A 0.3169 0.8724 0.5955 0.033 Uiso calc PR 0.50 1 A 1 H H4A 0.3142 0.7827 0.5433 0.033 Uiso d PR 0.50 1 A 2 C C1A 0.3878(7) 0.6681(4) 0.52552(17) 0.0208(7) Uani d . 1 1 . . C C2A 0.5752(7) 0.5422(4) 0.57071(16) 0.0209(7) Uani d . 1 1 A . Cl Cl2A 0.6697(2) 0.59588(10) 0.66033(4) 0.0281(2) Uani d . 1 1 . . C C3A 0.6859(7) 0.3776(4) 0.54496(17) 0.0214(7) Uani d . 1 1 . . H H3A 0.8143 0.2943 0.5759 0.026 Uiso calc R 1 1 A . 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 O1 0.0415(14) 0.0172(11) 0.0262(13) -0.0113(10) 0.0022(11) -0.0015(10) C1 0.0165(16) 0.0139(16) 0.0168(17) -0.0006(13) -0.0031(14) 0.0028(13) C2 0.0107(16) 0.0236(17) 0.0139(17) -0.0006(13) -0.0034(13) 0.0044(13) Cl2 0.0262(5) 0.0317(5) 0.0187(5) -0.0070(4) 0.0022(4) 0.0043(3) C3 0.0161(17) 0.0152(16) 0.0244(19) -0.0045(13) -0.0036(14) 0.0082(14) C4 0.0196(17) 0.0123(16) 0.0265(19) -0.0041(13) -0.0074(15) 0.0004(13) C5 0.0121(16) 0.0142(15) 0.0156(17) -0.0006(12) -0.0021(13) 0.0010(13) Cl5 0.0244(4) 0.0167(4) 0.0179(4) -0.0044(3) 0.0003(3) -0.0001(3) C6 0.0133(16) 0.0164(16) 0.0206(18) -0.0027(13) -0.0038(14) 0.0070(13) C7 0.0226(18) 0.0171(17) 0.0236(19) 0.0014(14) -0.0022(15) 0.0007(14) O1A 0.056(4) 0.017(3) 0.056(4) 0.012(3) -0.018(3) -0.003(3) C7A 0.037(4) 0.015(4) 0.029(4) -0.005(3) 0.002(3) -0.003(3) C1A 0.0169(17) 0.0193(17) 0.0262(19) -0.0054(14) 0.0035(15) 0.0047(14) C2A 0.0152(16) 0.0254(18) 0.0223(18) -0.0066(14) 0.0032(14) 0.0065(14) Cl2A 0.0245(5) 0.0387(5) 0.0218(5) -0.0074(4) -0.0022(4) 0.0042(4) C3A 0.0148(17) 0.0251(18) 0.0232(19) -0.0021(13) 0.0026(14) 0.0113(15) 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' 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C6 C1 C2 . . 117.6(2) C6 C1 C7 . . 118.9(2) C2 C1 C7 . . 123.5(3) C3 C2 C1 . . 121.8(3) C3 C2 Cl2 . . 118.1(2) C1 C2 Cl2 . . 120.1(2) C4 C3 C2 . . 119.1(2) C4 C3 H3 . . 120.5 C2 C3 H3 . . 120.5 C3 C4 C5 . . 120.2(3) C3 C4 H4 . . 119.9 C5 C4 H4 . . 119.9 C6 C5 C4 . . 120.7(3) C6 C5 Cl5 . . 118.8(2) C4 C5 Cl5 . . 120.4(2) C5 C6 C1 . . 120.6(2) C5 C6 H6 . . 119.7 C1 C6 H6 . . 119.7 O1 C7 C1 . . 123.7(3) O1 C7 H7 . . 118.2 C1 C7 H7 . . 118.2 O1A C7A C1A . . 125.5(6) O1A C7A H7A . . 117.2 C1A C7A H7A . . 117.2 C3A C1A C7A 2_666 . 116.6(4) C3A C1A C2A 2_666 . 118.8(3) C7A C1A C2A . . 124.5(4) C3A C1A H4A 2_666 . 120.7 C2A C1A H4A . . 120.5 C3A C2A C1A . . 120.7(3) C3A C2A Cl2A . . 119.4(2) C1A C2A Cl2A . . 119.9(2) C2A C3A C1A . 2_666 120.4(3) C2A C3A H3A . . 119.8 C1A C3A H3A 2_666 . 119.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C7 . 1.212(3) C1 C6 . 1.395(4) C1 C2 . 1.397(4) C1 C7 . 1.477(4) C2 C3 . 1.386(4) C2 Cl2 . 1.750(3) C3 C4 . 1.372(4) C3 H3 . 0.950 C4 C5 . 1.381(4) C4 H4 . 0.950 C5 C6 . 1.374(4) C5 Cl5 . 1.739(3) C6 H6 . 0.950 C7 H7 . 0.950 O1A C7A . 1.210(6) C7A C1A . 1.400(6) C7A H7A . 0.950 C1A C3A 2_666 1.377(4) C1A C2A . 1.407(4) C1A H4A . 0.950 C2A C3A . 1.369(4) C2A Cl2A . 1.741(3) C3A C1A 2_666 1.377(4) C3A H3A . 0.950 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion C6 C1 C2 C3 . . 2.0(4) C7 C1 C2 C3 . . -177.0(3) C6 C1 C2 Cl2 . . -178.6(2) C7 C1 C2 Cl2 . . 2.3(4) C1 C2 C3 C4 . . -2.0(4) Cl2 C2 C3 C4 . . 178.7(2) C2 C3 C4 C5 . . 0.8(4) C3 C4 C5 C6 . . 0.4(4) C3 C4 C5 Cl5 . . -179.4(2) C4 C5 C6 C1 . . -0.3(4) Cl5 C5 C6 C1 . . 179.5(2) C2 C1 C6 C5 . . -0.9(4) C7 C1 C6 C5 . . 178.2(3) C6 C1 C7 O1 . . -8.8(4) C2 C1 C7 O1 . . 170.2(3) O1A C7A C1A C3A . 2_666 2.4(7) O1A C7A C1A C2A . . -175.8(5) C3A C1A C2A C3A 2_666 . 0.6(5) C7A C1A C2A C3A . . 178.8(3) C3A C1A C2A Cl2A 2_666 . -179.6(2) C7A C1A C2A Cl2A . . -1.4(5) C1A C2A C3A C1A . 2_666 -0.6(5) Cl2A C2A C3A C1A . 2_666 179.6(2)