#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104974.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_2104974 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 2,3-dichlorobenzaldehyde _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 _cell_angle_alpha 90.00 _cell_angle_beta 90.979(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 3.7888(3) _cell_length_b 13.7784(15) _cell_length_c 13.0368(15) _cell_measurement_reflns_used 3550 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 24.81 _cell_measurement_theta_min 2.96 _cell_volume 680.47(12) _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 0.985 _diffrn_measured_fraction_theta_max 0.985 _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 0.0486 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 11531 _diffrn_reflns_theta_full 25.31 _diffrn_reflns_theta_max 25.31 _diffrn_reflns_theta_min 4.30 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.865 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.751 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Sheldrick, 2003) Ratio of minimum to maximum apparent transmission: 0.751021 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.627 _refine_diff_density_min -0.375 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 91 _refine_ls_number_reflns 1226 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.127 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0381 _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^)+(0.0365P)^2^+1.0914P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0892 _refine_ls_wR_factor_ref 0.0927 _reflns_number_gt 1036 _reflns_number_total 1226 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 1 in P2(1)/c CELL 0.71073 3.7888 13.7784 13.0368 90.000 90.979 90.000 ZERR 4.00 0.0003 0.0015 0.0015 0.000 0.005 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H O CL UNIT 28 16 4 8 TEMP -153 L.S. 20 EQIV $1 2-X, 2-Y, 1-Z EQIV $2 1+X, 1.5-Y, 0.5+Z BIND O1 CL2_$1 BIND O1 CL3_$2 BOND $H HTAB 2 ACTA CONF LIST 4 FMAP 2 PLAN -5 SHEL 5.8 0 WGHT 0.036500 1.091400 FVAR 0.57969 CL2 4 0.69778 0.85196 0.44125 11.00000 0.02384 0.01555 = 0.01997 0.00447 -0.00320 0.00054 CL3 4 0.61766 0.62727 0.41170 11.00000 0.02176 0.01722 = 0.01947 -0.00287 -0.00337 -0.00081 O1 3 1.28203 0.94542 0.70410 11.00000 0.03586 0.01646 = 0.02578 -0.00332 -0.00859 -0.00209 C1 1 1.01174 0.80865 0.62527 11.00000 0.01416 0.01363 = 0.01914 -0.00092 0.00255 -0.00040 C2 1 0.84543 0.77347 0.53664 11.00000 0.01371 0.01532 = 0.01465 0.00446 0.00118 0.00240 C3 1 0.80296 0.67346 0.52380 11.00000 0.01382 0.01498 = 0.01688 -0.00239 0.00011 -0.00176 C4 1 0.91642 0.61050 0.59958 11.00000 0.01936 0.01273 = 0.01929 0.00049 0.00311 0.00004 AFIX 43 H4 2 0.88152 0.54267 0.59115 11.00000 -1.20000 AFIX 0 C5 1 1.07945 0.64486 0.68717 11.00000 0.01915 0.01716 = 0.02158 0.00502 0.00024 0.00103 AFIX 43 H5 2 1.15855 0.60085 0.73873 11.00000 -1.20000 AFIX 0 C6 1 1.12850 0.74372 0.70030 11.00000 0.01755 0.01853 = 0.01655 -0.00194 0.00037 -0.00108 AFIX 43 H6 2 1.24237 0.76734 0.76080 11.00000 -1.20000 AFIX 0 C7 1 1.07749 0.91386 0.64108 11.00000 0.02268 0.01688 = 0.02292 -0.00062 0.00199 0.00069 AFIX 43 H7 2 0.95089 0.95867 0.59905 11.00000 -1.20000 AFIX 0 HKLF 4 END ; _cod_data_source_file gp5044.cif _cod_data_source_block 1 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2104974 _cod_database_fobs_code 2104974 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_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 Cl Cl2 0.69778(19) 0.85196(5) 0.44125(6) 0.0198(2) Uani d . 1 1 Cl Cl3 0.61767(19) 0.62727(5) 0.41170(6) 0.0195(2) Uani d . 1 1 O O1 1.2820(6) 0.94542(15) 0.70410(17) 0.0261(5) Uani d . 1 1 C C1 1.0117(7) 0.8087(2) 0.6253(2) 0.0156(6) Uani d . 1 1 C C2 0.8454(7) 0.7735(2) 0.5366(2) 0.0146(6) Uani d . 1 1 C C3 0.8030(7) 0.6735(2) 0.5238(2) 0.0152(6) Uani d . 1 1 C C4 0.9164(7) 0.6105(2) 0.5996(2) 0.0171(6) Uani d . 1 1 H H4 0.8815 0.5427 0.5911 0.021 Uiso calc R 1 1 C C5 1.0795(8) 0.6449(2) 0.6872(2) 0.0193(7) Uani d . 1 1 H H5 1.1586 0.6008 0.7387 0.023 Uiso calc R 1 1 C C6 1.1285(7) 0.7437(2) 0.7003(2) 0.0175(6) Uani d . 1 1 H H6 1.2424 0.7673 0.7608 0.021 Uiso calc R 1 1 C C7 1.0775(8) 0.9139(2) 0.6411(2) 0.0208(7) Uani d . 1 1 H H7 0.9509 0.9587 0.5990 0.025 Uiso calc R 1 1 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 Cl2 0.0238(4) 0.0155(4) 0.0200(4) 0.0005(3) -0.0032(3) 0.0045(3) Cl3 0.0218(4) 0.0172(4) 0.0195(4) -0.0008(3) -0.0034(3) -0.0029(3) O1 0.0359(13) 0.0165(11) 0.0258(13) -0.0021(10) -0.0086(10) -0.0033(9) C1 0.0142(14) 0.0136(14) 0.0191(16) -0.0004(11) 0.0025(12) -0.0009(12) C2 0.0137(14) 0.0153(14) 0.0147(15) 0.0024(11) 0.0012(11) 0.0045(12) C3 0.0138(14) 0.0150(15) 0.0169(15) -0.0018(11) 0.0001(11) -0.0024(12) C4 0.0194(15) 0.0127(14) 0.0193(16) 0.0000(12) 0.0031(12) 0.0005(12) C5 0.0191(15) 0.0172(15) 0.0216(17) 0.0010(12) 0.0002(12) 0.0050(12) C6 0.0175(14) 0.0185(15) 0.0166(16) -0.0011(12) 0.0004(12) -0.0019(12) C7 0.0227(16) 0.0169(16) 0.0229(17) 0.0007(13) 0.0020(13) -0.0006(13) 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 C6 C1 C2 119.5(3) C6 C1 C7 118.6(3) C2 C1 C7 121.8(3) C1 C2 C3 119.5(3) C1 C2 Cl2 120.9(2) C3 C2 Cl2 119.6(2) C4 C3 C2 120.1(3) C4 C3 Cl3 119.4(2) C2 C3 Cl3 120.5(2) C5 C4 C3 120.6(3) C5 C4 H4 119.7 C3 C4 H4 119.7 C4 C5 C6 120.0(3) C4 C5 H5 120.0 C6 C5 H5 120.0 C5 C6 C1 120.3(3) C5 C6 H6 119.8 C1 C6 H6 119.8 O1 C7 C1 123.6(3) O1 C7 H7 118.2 C1 C7 H7 118.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl2 C2 1.734(3) Cl3 C3 1.732(3) O1 C7 1.201(4) C1 C6 1.392(4) C1 C2 1.394(4) C1 C7 1.485(4) C2 C3 1.397(4) C3 C4 1.378(4) C4 C5 1.373(4) C4 H4 0.950 C5 C6 1.385(4) C5 H5 0.950 C6 H6 0.950 C7 H7 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 C6 C1 C2 C3 -0.9(4) C7 C1 C2 C3 177.4(3) C6 C1 C2 Cl2 -179.8(2) C7 C1 C2 Cl2 -1.4(4) C1 C2 C3 C4 1.7(4) Cl2 C2 C3 C4 -179.4(2) C1 C2 C3 Cl3 -176.7(2) Cl2 C2 C3 Cl3 2.2(3) C2 C3 C4 C5 -1.6(4) Cl3 C3 C4 C5 176.9(2) C3 C4 C5 C6 0.5(4) C4 C5 C6 C1 0.3(4) C2 C1 C6 C5 -0.1(4) C7 C1 C6 C5 -178.5(3) C6 C1 C7 O1 14.9(4) C2 C1 C7 O1 -163.5(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 32881 2 PubChem 35745