#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104977.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_2104977 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 3,5-dichlorobenzaldehyde _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 91.546(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 3.7785(5) _cell_length_b 31.353(5) _cell_length_c 12.058(2) _cell_measurement_reflns_used 1496 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 20.83 _cell_measurement_theta_min 3.44 _cell_volume 1428.0(4) _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 0.984 _diffrn_measured_fraction_theta_max 0.984 _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 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0790 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 13283 _diffrn_reflns_theta_full 25.68 _diffrn_reflns_theta_max 25.68 _diffrn_reflns_theta_min 3.62 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.824 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_correction_T_min 0.698 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Ratio of minimum to maximum apparent transmission: 0.703457 SADABS v.2.10 (Sheldrick, 2003) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.628 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.376 _refine_diff_density_min -0.348 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2678 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0457 _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^)+(0.0444P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0877 _refine_ls_wR_factor_ref 0.0981 _reflns_number_gt 1731 _reflns_number_total 2678 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL 6 in P2(1)/n CELL 0.71073 3.7785 31.3531 12.0582 90.000 91.546 90.000 ZERR 8.00 0.0005 0.0046 0.0020 0.000 0.006 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O CL UNIT 56 32 8 16 SIZE 0.30 0.15 0.01 TEMP -153 L.S. 10 BOND $H ACTA CONF LIST 4 FMAP 2 PLAN -5 SHEL 5.8 0 WGHT 0.044400 FVAR 0.31772 O1 3 0.165754 0.192589 0.145080 11.00000 0.02908 0.03529 = 0.02068 -0.00055 -0.00854 -0.00258 C1 1 0.442910 0.174296 0.318498 11.00000 0.01286 0.01992 = 0.01523 -0.00013 0.00115 -0.00117 C2 1 0.380404 0.130523 0.310995 11.00000 0.01402 0.02511 = 0.01793 -0.00418 0.00102 -0.00042 AFIX 43 H2A 2 0.270040 0.118548 0.246482 11.00000 -1.20000 AFIX 0 C3 1 0.482848 0.104973 0.399658 11.00000 0.01137 0.01932 = 0.02358 -0.00316 0.00220 -0.00008 CL3 4 0.399222 0.050566 0.393584 11.00000 0.03402 0.01774 = 0.03246 -0.00101 -0.00094 -0.00402 C4 1 0.646248 0.121552 0.494297 11.00000 0.01266 0.02444 = 0.01672 0.00430 0.00113 0.00124 AFIX 43 H4A 2 0.715712 0.103534 0.554371 11.00000 -1.20000 AFIX 0 C5 1 0.705716 0.165051 0.499083 11.00000 0.01154 0.02526 = 0.01404 0.00031 -0.00228 -0.00046 CL5 4 0.905109 0.186815 0.617957 11.00000 0.02205 0.02825 = 0.01856 -0.00472 -0.00460 0.00025 C6 1 0.606483 0.191752 0.412963 11.00000 0.01574 0.01852 = 0.02104 -0.00263 0.00316 -0.00096 AFIX 43 H6A 2 0.648901 0.221566 0.417921 11.00000 -1.20000 AFIX 0 C7 1 0.331671 0.203254 0.227865 11.00000 0.02482 0.02332 = 0.02242 0.00439 -0.00068 -0.00081 AFIX 43 H7A 2 0.394782 0.232479 0.234867 11.00000 -1.20000 AFIX 0 O1A 3 0.366214 0.210947 0.847492 11.00000 0.04231 0.02249 = 0.02735 0.00088 -0.00688 0.01102 C1A 1 0.557050 0.142813 0.912336 11.00000 0.01307 0.01835 = 0.01953 0.00051 0.00179 0.00309 C2A 1 0.424948 0.120590 0.820077 11.00000 0.01351 0.02754 = 0.01441 0.00101 -0.00254 0.00044 AFIX 43 H2AA 2 0.324930 0.135354 0.757979 11.00000 -1.20000 AFIX 0 C3A 1 0.442853 0.076705 0.821070 11.00000 0.01579 0.01984 = 0.01579 -0.00140 0.00451 -0.00056 CL3A 4 0.279375 0.048102 0.707194 11.00000 0.02419 0.02793 = 0.01902 -0.00356 -0.00400 -0.00169 C4A 1 0.586901 0.054411 0.911211 11.00000 0.01323 0.01794 = 0.02042 0.00389 0.00396 -0.00160 AFIX 43 H4AA 2 0.597741 0.024140 0.910699 11.00000 -1.20000 AFIX 0 C5A 1 0.714110 0.077490 1.001726 11.00000 0.00912 0.02345 = 0.01908 0.00313 -0.00137 -0.00031 CL5A 4 0.888589 0.050356 1.116183 11.00000 0.02237 0.02466 = 0.01974 0.00519 -0.00470 0.00054 C6A 1 0.703117 0.121609 1.003321 11.00000 0.01198 0.02508 = 0.01645 0.00029 0.00253 -0.00375 AFIX 43 H6AA 2 0.794004 0.137043 1.065618 11.00000 -1.20000 AFIX 0 C7A 1 0.534222 0.190011 0.914642 11.00000 0.02477 0.02254 = 0.01984 0.00071 0.00356 -0.00083 AFIX 43 H7AA 2 0.659226 0.204698 0.972404 11.00000 -1.20000 AFIX 0 HKLF 4 END ; _cod_data_source_file gp5044.cif _cod_data_source_block 6 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2104977 _cod_database_fobs_code 2104977 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 O O1 0.1658(7) 0.19259(7) 0.1451(2) 0.0285(6) Uani d . 1 1 C C1 0.4429(8) 0.17430(10) 0.3185(3) 0.0160(8) Uani d . 1 1 C C2 0.3804(9) 0.13052(10) 0.3110(3) 0.0190(8) Uani d . 1 1 H H2 0.2700 0.1185 0.2465 0.023 Uiso calc R 1 1 C C3 0.4828(9) 0.10497(10) 0.3997(3) 0.0181(8) Uani d . 1 1 Cl Cl3 0.3992(3) 0.05057(3) 0.39358(7) 0.0281(3) Uani d . 1 1 C C4 0.6462(8) 0.12155(10) 0.4943(3) 0.0179(8) Uani d . 1 1 H H4 0.7157 0.1035 0.5544 0.022 Uiso calc R 1 1 C C5 0.7057(9) 0.16505(11) 0.4991(3) 0.0170(8) Uani d . 1 1 Cl Cl5 0.9051(2) 0.18681(3) 0.61796(7) 0.0230(2) Uani d . 1 1 C C6 0.6065(9) 0.19175(11) 0.4130(3) 0.0184(8) Uani d . 1 1 H H6 0.6489 0.2216 0.4179 0.022 Uiso calc R 1 1 C C7 0.3317(9) 0.20325(11) 0.2279(3) 0.0235(9) Uani d . 1 1 H H7 0.3948 0.2325 0.2349 0.028 Uiso calc R 1 1 O O1A 0.3662(7) 0.21095(7) 0.8475(2) 0.0309(7) Uani d . 1 1 C C1A 0.5570(9) 0.14281(10) 0.9123(3) 0.0170(8) Uani d . 1 1 C C2A 0.4249(8) 0.12059(10) 0.8201(3) 0.0185(8) Uani d . 1 1 H H2A 0.3249 0.1354 0.7580 0.022 Uiso calc R 1 1 C C3A 0.4429(8) 0.07671(10) 0.8211(3) 0.0171(8) Uani d . 1 1 Cl Cl3A 0.2794(2) 0.04810(3) 0.70719(7) 0.0238(2) Uani d . 1 1 C C4A 0.5869(8) 0.05441(10) 0.9112(3) 0.0171(8) Uani d . 1 1 H H4A 0.5977 0.0241 0.9107 0.021 Uiso calc R 1 1 C C5A 0.7141(9) 0.07749(11) 1.0017(3) 0.0172(8) Uani d . 1 1 Cl Cl5A 0.8886(2) 0.05036(3) 1.11618(7) 0.0224(2) Uani d . 1 1 C C6A 0.7031(8) 0.12161(10) 1.0033(3) 0.0178(8) Uani d . 1 1 H H6A 0.7940 0.1370 1.0656 0.021 Uiso calc R 1 1 C C7A 0.5342(9) 0.19001(11) 0.9146(3) 0.0223(9) Uani d . 1 1 H H7A 0.6592 0.2047 0.9724 0.027 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 O1 0.0291(17) 0.0353(15) 0.0207(15) -0.0026(12) -0.0085(12) -0.0005(12) C1 0.013(2) 0.0199(19) 0.0152(19) -0.0012(14) 0.0012(15) -0.0001(15) C2 0.014(2) 0.025(2) 0.018(2) -0.0004(15) 0.0010(15) -0.0042(15) C3 0.011(2) 0.0193(19) 0.024(2) -0.0001(14) 0.0022(16) -0.0032(15) Cl3 0.0340(6) 0.0177(5) 0.0325(6) -0.0040(4) -0.0009(4) -0.0010(4) C4 0.013(2) 0.024(2) 0.0167(19) 0.0012(15) 0.0011(15) 0.0043(15) C5 0.012(2) 0.025(2) 0.0140(19) -0.0005(15) -0.0023(15) 0.0003(15) Cl5 0.0220(6) 0.0283(5) 0.0186(5) 0.0002(4) -0.0046(4) -0.0047(4) C6 0.016(2) 0.0185(19) 0.0210(19) -0.0010(15) 0.0032(15) -0.0026(15) C7 0.025(3) 0.023(2) 0.022(2) -0.0008(17) -0.0007(18) 0.0044(17) O1A 0.0423(18) 0.0225(14) 0.0274(15) 0.0110(13) -0.0069(13) 0.0009(12) C1A 0.013(2) 0.0184(19) 0.0195(19) 0.0031(15) 0.0018(15) 0.0005(15) C2A 0.014(2) 0.028(2) 0.0144(19) 0.0004(15) -0.0025(15) 0.0010(15) C3A 0.016(2) 0.020(2) 0.0158(19) -0.0006(15) 0.0045(15) -0.0014(15) Cl3A 0.0242(6) 0.0279(5) 0.0190(5) -0.0017(4) -0.0040(4) -0.0036(4) C4A 0.013(2) 0.0179(19) 0.0204(19) -0.0016(15) 0.0040(15) 0.0039(16) C5A 0.009(2) 0.023(2) 0.019(2) -0.0003(15) -0.0014(15) 0.0031(16) Cl5A 0.0224(6) 0.0247(5) 0.0197(5) 0.0005(4) -0.0047(4) 0.0052(4) C6A 0.012(2) 0.025(2) 0.0164(19) -0.0038(15) 0.0025(15) 0.0003(16) C7A 0.025(2) 0.023(2) 0.020(2) -0.0008(17) 0.0036(17) 0.0007(17) 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 120.7(3) C6 C1 C7 118.4(3) C2 C1 C7 120.9(3) C3 C2 C1 118.4(3) C3 C2 H2 120.8 C1 C2 H2 120.8 C2 C3 C4 122.0(3) C2 C3 Cl3 119.3(3) C4 C3 Cl3 118.7(3) C5 C4 C3 118.2(3) C5 C4 H4 120.9 C3 C4 H4 120.9 C6 C5 C4 121.8(3) C6 C5 Cl5 119.0(3) C4 C5 Cl5 119.2(3) C5 C6 C1 118.9(3) C5 C6 H6 120.6 C1 C6 H6 120.6 O1 C7 C1 124.9(3) O1 C7 H7 117.6 C1 C7 H7 117.6 C6A C1A C2A 121.3(3) C6A C1A C7A 119.1(3) C2A C1A C7A 119.6(3) C3A C2A C1A 118.4(3) C3A C2A H2A 120.8 C1A C2A H2A 120.8 C2A C3A C4A 121.8(3) C2A C3A Cl3A 119.5(3) C4A C3A Cl3A 118.7(3) C5A C4A C3A 118.3(3) C5A C4A H4A 120.9 C3A C4A H4A 120.9 C6A C5A C4A 121.6(3) C6A C5A Cl5A 119.3(3) C4A C5A Cl5A 119.1(3) C5A C6A C1A 118.7(3) C5A C6A H6A 120.6 C1A C6A H6A 120.6 O1A C7A C1A 124.0(3) O1A C7A H7A 118.0 C1A C7A H7A 118.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.211(4) C1 C6 1.393(4) C1 C2 1.395(4) C1 C7 1.473(4) C2 C3 1.383(4) C2 H2 0.950 C3 C4 1.384(4) C3 Cl3 1.736(3) C4 C5 1.383(4) C4 H4 0.950 C5 C6 1.378(4) C5 Cl5 1.741(3) C6 H6 0.950 C7 H7 0.950 O1A C7A 1.209(4) C1A C6A 1.385(4) C1A C2A 1.394(4) C1A C7A 1.483(4) C2A C3A 1.378(4) C2A H2A 0.950 C3A C4A 1.391(4) C3A Cl3A 1.739(3) C4A C5A 1.385(4) C4A H4A 0.950 C5A C6A 1.384(4) C5A Cl5A 1.736(3) C6A H6A 0.950 C7A H7A 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 0.3(5) C7 C1 C2 C3 -178.5(3) C1 C2 C3 C4 -0.4(5) C1 C2 C3 Cl3 178.6(2) C2 C3 C4 C5 0.2(5) Cl3 C3 C4 C5 -178.8(2) C3 C4 C5 C6 0.1(5) C3 C4 C5 Cl5 179.1(2) C4 C5 C6 C1 -0.2(5) Cl5 C5 C6 C1 -179.2(3) C2 C1 C6 C5 0.0(5) C7 C1 C6 C5 178.8(3) C6 C1 C7 O1 -174.6(3) C2 C1 C7 O1 4.2(6) C6A C1A C2A C3A -0.1(5) C7A C1A C2A C3A -178.7(3) C1A C2A C3A C4A 0.2(5) C1A C2A C3A Cl3A 179.9(2) C2A C3A C4A C5A 0.1(5) Cl3A C3A C4A C5A -179.6(3) C3A C4A C5A C6A -0.6(5) C3A C4A C5A Cl5A 179.0(2) C4A C5A C6A C1A 0.8(5) Cl5A C5A C6A C1A -178.8(2) C2A C1A C6A C5A -0.4(5) C7A C1A C6A C5A 178.2(3) C6A C1A C7A O1A -168.6(3) C2A C1A C7A O1A 10.0(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 32882 2 PubChem 139064043