#------------------------------------------------------------------------------ #$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201974 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/81/2218181.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_2218181 loop_ _publ_author_name 'Azizul, Isha' 'Ng, Seik Weng' _publ_section_title ; 3,5-Dichlorosalicylaldehyde ; _journal_coeditor_code LH2606 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o917 _journal_paper_doi 10.1107/S1600536808011021 _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C7 H4 Cl2 O2' _chemical_formula_moiety 'C7 H4 Cl2 O2' _chemical_formula_sum 'C7 H4 Cl2 O2' _chemical_formula_weight 191.00 _chemical_name_common ; 3,5-Dichlorosalicylaldehyde ; _chemical_name_systematic ; 3,5-dichloro-2-hydroxybenzaldehyde ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 115.185(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.2823(2) _cell_length_b 13.7412(3) _cell_length_c 7.0973(2) _cell_measurement_reflns_used 3128 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.2 _cell_measurement_theta_min 3.0 _cell_volume 730.95(3) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'publCIF (Westrip, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART APEXII' _diffrn_measurement_method \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 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 8436 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.72 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_correction_T_min 0.701 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.592 _refine_diff_density_min -0.491 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 104 _refine_ls_number_reflns 1672 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0369 _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^)+(0.0416P)^2^+0.8939P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.1008 _reflns_number_gt 1303 _reflns_number_total 1672 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh2606.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2218181 _cod_database_fobs_code 2218181 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 Cl Cl1 0.17794(9) 0.14230(4) 0.48280(10) 0.01972(18) Uani d . 1 Cl Cl2 0.15345(9) 0.53148(4) 0.39904(11) 0.02166(19) Uani d . 1 O O1 0.5328(3) 0.17615(13) 0.8080(3) 0.0200(4) Uani d D 1 H H1 0.631(3) 0.192(3) 0.905(4) 0.038(10) Uiso d D 1 O O2 0.7916(3) 0.28892(14) 1.0580(3) 0.0252(4) Uani d . 1 C C1 0.4488(3) 0.25960(17) 0.7232(4) 0.0155(5) Uani d . 1 C C2 0.2766(3) 0.25497(17) 0.5629(4) 0.0164(5) Uani d . 1 C C3 0.1851(4) 0.33804(17) 0.4659(4) 0.0168(5) Uani d . 1 H H3 0.0680 0.3339 0.3572 0.020 Uiso calc R 1 C C4 0.2680(4) 0.42815(17) 0.5306(4) 0.0177(5) Uani d . 1 C C5 0.4355(4) 0.43592(17) 0.6906(4) 0.0179(5) Uani d . 1 H H5 0.4890 0.4980 0.7336 0.021 Uiso calc R 1 C C6 0.5266(3) 0.35155(17) 0.7897(4) 0.0160(5) Uani d . 1 C C7 0.7028(4) 0.35892(18) 0.9634(4) 0.0206(6) Uani d . 1 H H7 0.7517 0.4220 1.0058 0.025 Uiso calc R 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 Cl1 0.0225(3) 0.0110(3) 0.0228(3) -0.0036(2) 0.0068(3) -0.0026(2) Cl2 0.0204(3) 0.0122(3) 0.0276(4) 0.0029(2) 0.0056(3) 0.0051(2) O1 0.0193(10) 0.0111(8) 0.0243(11) 0.0025(7) 0.0042(9) 0.0025(7) O2 0.0211(10) 0.0197(9) 0.0272(11) 0.0004(8) 0.0030(9) 0.0033(8) C1 0.0182(13) 0.0111(10) 0.0180(12) 0.0028(9) 0.0083(11) 0.0016(9) C2 0.0216(13) 0.0106(10) 0.0186(12) -0.0017(9) 0.0100(11) -0.0016(9) C3 0.0163(13) 0.0162(12) 0.0172(13) -0.0004(9) 0.0063(11) -0.0007(9) C4 0.0201(14) 0.0114(11) 0.0213(13) 0.0038(9) 0.0086(12) 0.0032(9) C5 0.0202(14) 0.0108(11) 0.0228(14) -0.0024(9) 0.0093(12) 0.0000(9) C6 0.0151(13) 0.0123(11) 0.0195(13) -0.0004(9) 0.0064(11) 0.0003(9) C7 0.0212(14) 0.0149(12) 0.0229(14) -0.0029(10) 0.0068(12) -0.0003(10) 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 C1 O1 H1 107(3) O1 C1 C2 118.7(2) O1 C1 C6 122.7(2) C2 C1 C6 118.5(2) C3 C2 C1 121.5(2) C3 C2 Cl1 119.6(2) C1 C2 Cl1 118.96(18) C2 C3 C4 118.7(2) C2 C3 H3 120.6 C4 C3 H3 120.6 C5 C4 C3 121.6(2) C5 C4 Cl2 120.53(19) C3 C4 Cl2 117.9(2) C4 C5 C6 119.4(2) C4 C5 H5 120.3 C6 C5 H5 120.3 C5 C6 C1 120.3(2) C5 C6 C7 119.9(2) C1 C6 C7 119.8(2) O2 C7 C6 124.1(2) O2 C7 H7 118.0 C6 C7 H7 118.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C2 1.730(2) Cl2 C4 1.742(2) O1 C1 1.343(3) O1 H1 0.840(10) O2 C7 1.223(3) C1 C2 1.397(4) C1 C6 1.406(3) C2 C3 1.381(3) C3 C4 1.395(3) C3 H3 0.9500 C4 C5 1.373(4) C5 C6 1.399(3) C5 H5 0.9500 C6 C7 1.459(4) C7 H7 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1 O2 0.840(10) 1.87(2) 2.628(3) 149(3) yes 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 O1 C1 C2 C3 -178.3(2) C6 C1 C2 C3 2.0(4) O1 C1 C2 Cl1 0.8(3) C6 C1 C2 Cl1 -178.90(18) C1 C2 C3 C4 0.1(4) Cl1 C2 C3 C4 -179.03(19) C2 C3 C4 C5 -1.5(4) C2 C3 C4 Cl2 177.52(18) C3 C4 C5 C6 0.9(4) Cl2 C4 C5 C6 -178.17(19) C4 C5 C6 C1 1.3(4) C4 C5 C6 C7 -178.4(2) O1 C1 C6 C5 177.7(2) C2 C1 C6 C5 -2.7(4) O1 C1 C6 C7 -2.6(4) C2 C1 C6 C7 177.1(2) C5 C6 C7 O2 -179.8(3) C1 C6 C7 O2 0.5(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 60027