#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203246.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_2203246 loop_ _publ_author_name 'Beghidja, Adel' 'Benboudiaf, Ali' 'Beghidja, Chahrazed' 'Welter, Richard' _publ_section_title ; 2-Chloro-3-chloromethylbenzo[h]quinoline ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o228 _journal_page_last o229 _journal_paper_doi 10.1107/S1600536804000650 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H9 Cl2 N' _chemical_formula_moiety 'C14 H9 Cl2 N' _chemical_formula_sum 'C14 H9 Cl2 N' _chemical_formula_weight 262.12 _chemical_name_systematic ; 2-Chloro-3-chloromethylbenzo[h]quinoline ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 79.21(10) _cell_angle_beta 76.19(10) _cell_angle_gamma 85.84(10) _cell_formula_units_Z 2 _cell_length_a 6.9211(10) _cell_length_b 8.3176(10) _cell_length_c 10.6480(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.96 _cell_measurement_theta_min 2.49 _cell_volume 584.5(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'PLATON98 (Spek, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _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 0.0849 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 3498 _diffrn_reflns_theta_full 29.96 _diffrn_reflns_theta_max 29.96 _diffrn_reflns_theta_min 2.49 _diffrn_standards_decay_% 2 _diffrn_standards_interval_time 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.528 _exptl_absorpt_correction_type none _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.410 _refine_diff_density_min -0.351 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 3288 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.1213 _refine_ls_R_factor_gt 0.0601 _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^)+(0.0861P)^2^+0.6126P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1585 _refine_ls_wR_factor_ref 0.2095 _reflns_number_gt 2022 _reflns_number_total 3288 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ww6143.cif _cod_data_source_block I _cod_database_code 2203246 _cod_database_fobs_code 2203246 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_occupancy _atom_site_type_symbol Cl1 0.28019(15) 0.70060(15) 0.16077(9) 0.0591(3) Uani d 1 Cl Cl2 0.82046(18) 0.68971(13) -0.00730(9) 0.0620(3) Uani d 1 Cl N1 0.3487(4) 0.7533(3) 0.3781(2) 0.0354(6) Uani d 1 N C12 0.3725(5) 0.8215(4) 0.5841(3) 0.0343(6) Uani d 1 C C13 0.4594(4) 0.7496(4) 0.4678(3) 0.0323(6) Uani d 1 C C1 0.4295(5) 0.6894(4) 0.2745(3) 0.0370(7) Uani d 1 C C4 0.6520(5) 0.6802(4) 0.4515(3) 0.0371(7) Uani d 1 C C2 0.6185(5) 0.6131(4) 0.2473(3) 0.0376(7) Uani d 1 C C7 0.4866(5) 0.8197(4) 0.6778(3) 0.0412(7) Uani d 1 C C3 0.7278(5) 0.6109(4) 0.3398(3) 0.0399(7) Uani d 1 C H3 0.8547 0.5623 0.3275 0.048 Uiso calc 1 H C11 0.1802(5) 0.8921(4) 0.6047(3) 0.0438(7) Uani d 1 C H11 0.1041 0.8931 0.5434 0.053 Uiso calc 1 H C6 0.6826(6) 0.7478(5) 0.6567(3) 0.0495(9) Uani d 1 C H6 0.7574 0.7471 0.7187 0.059 Uiso calc 1 H C8 0.4022(7) 0.8905(5) 0.7894(3) 0.0530(10) Uani d 1 C H8 0.4751 0.8906 0.8523 0.064 Uiso calc 1 H C14 0.7003(6) 0.5386(5) 0.1273(4) 0.0495(8) Uani d 1 C H14A 0.5931 0.4917 0.1030 0.059 Uiso calc 1 H H14B 0.7954 0.4512 0.1462 0.059 Uiso calc 1 H C9 0.2150(7) 0.9588(5) 0.8064(4) 0.0578(11) Uani d 1 C H9 0.1619 1.0053 0.8806 0.069 Uiso calc 1 H C5 0.7623(5) 0.6809(5) 0.5490(4) 0.0488(8) Uani d 1 C H5 0.8903 0.6347 0.5381 0.059 Uiso calc 1 H C10 0.1032(6) 0.9600(5) 0.7149(4) 0.0558(10) Uani d 1 C H10 -0.0246 1.0069 0.7279 0.067 Uiso calc 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 0.0548(6) 0.0861(7) 0.0473(5) 0.0077(5) -0.0227(4) -0.0285(5) Cl2 0.0784(7) 0.0620(6) 0.0361(4) -0.0011(5) 0.0046(4) -0.0083(4) N1 0.0329(13) 0.0424(14) 0.0328(12) -0.0017(11) -0.0075(10) -0.0111(10) C12 0.0390(16) 0.0332(15) 0.0293(13) -0.0074(12) -0.0052(11) -0.0034(11) C13 0.0338(15) 0.0313(14) 0.0303(13) -0.0045(11) -0.0061(11) -0.0023(11) C1 0.0388(16) 0.0423(17) 0.0321(14) -0.0033(13) -0.0102(12) -0.0083(12) C4 0.0337(15) 0.0410(16) 0.0358(15) -0.0024(12) -0.0089(12) -0.0033(12) C2 0.0399(17) 0.0365(16) 0.0334(14) -0.0014(13) -0.0009(12) -0.0079(12) C7 0.0520(19) 0.0392(17) 0.0324(14) -0.0157(14) -0.0091(13) -0.0017(12) C3 0.0308(15) 0.0426(17) 0.0415(16) -0.0001(13) -0.0017(12) -0.0043(13) C11 0.0458(18) 0.0443(18) 0.0413(17) 0.0007(15) -0.0060(14) -0.0134(14) C6 0.051(2) 0.062(2) 0.0403(17) -0.0094(17) -0.0220(15) -0.0022(16) C8 0.079(3) 0.051(2) 0.0326(16) -0.021(2) -0.0116(17) -0.0111(14) C14 0.054(2) 0.0494(19) 0.0405(17) 0.0014(16) 0.0022(15) -0.0137(15) C9 0.083(3) 0.048(2) 0.0387(17) -0.016(2) 0.0058(18) -0.0191(15) C5 0.0378(17) 0.061(2) 0.0482(19) -0.0014(16) -0.0160(15) -0.0022(16) C10 0.057(2) 0.051(2) 0.055(2) 0.0011(18) 0.0054(18) -0.0193(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' Cl Cl 0.1484 0.1585 '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' 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 C13 117.1(3) yes C11 C12 C7 119.5(3) no C11 C12 C13 121.9(3) no C7 C12 C13 118.7(3) no N1 C13 C4 122.2(3) yes N1 C13 C12 118.0(3) yes C4 C13 C12 119.8(3) no N1 C1 C2 126.6(3) yes N1 C1 Cl1 115.0(2) yes C2 C1 Cl1 118.4(2) yes C3 C4 C13 117.8(3) no C3 C4 C5 122.5(3) no C13 C4 C5 119.7(3) no C3 C2 C1 115.1(3) no C3 C2 C14 121.0(3) no C1 C2 C14 123.8(3) no C8 C7 C12 118.3(4) no C8 C7 C6 122.2(3) no C12 C7 C6 119.5(3) no C2 C3 C4 121.1(3) no C10 C11 C12 120.4(3) no C5 C6 C7 121.6(3) no C9 C8 C7 120.8(3) no C2 C14 Cl2 110.8(3) no C8 C9 C10 120.9(3) no C6 C5 C4 120.7(3) no C11 C10 C9 120.1(4) no C2 C3 H3 119.3 no C4 C3 H3 119.3 no C10 C11 H11 119.7 no C12 C11 H11 119.7 no C5 C6 H6 119.2 no C7 C6 H6 119.2 no C9 C8 H8 119.6 no C7 C8 H8 119.6 no C2 C14 H14A 109.6 no Cl2 C14 H14A 109.6 no C2 C14 H14B 109.6 no Cl2 C14 H14B 109.6 no H14A C14 H14B 108.1 no C8 C9 H9 119.4 no C10 C9 H9 119.4 no C6 C5 H5 119.6 no C4 C5 H5 119.6 no C11 C10 H10 120.1 no C9 C10 H10 120.1 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C1 1.756(3) yes Cl2 C14 1.799(4) yes N1 C1 1.302(4) yes N1 C13 1.354(4) yes C12 C11 1.400(5) no C12 C7 1.410(4) no C12 C13 1.457(4) no C13 C4 1.398(4) no C1 C2 1.402(5) no C4 C3 1.392(4) no C4 C5 1.428(5) no C2 C3 1.375(5) no C2 C14 1.496(4) no C7 C8 1.407(5) no C7 C6 1.427(6) no C11 C10 1.373(5) no C6 C5 1.350(5) no C8 C9 1.361(7) no C9 C10 1.379(6) no C3 H3 0.9300 no C11 H11 0.9300 no C6 H6 0.9300 no C8 H8 0.9300 no C14 H14A 0.9700 no C14 H14B 0.9700 no C9 H9 0.9300 no C5 H5 0.9300 no C10 H10 0.9300 no 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 C1 N1 C13 C4 -0.3(4) C1 N1 C13 C12 179.5(3) C11 C12 C13 N1 0.3(4) C7 C12 C13 N1 -179.5(3) C11 C12 C13 C4 -179.9(3) C7 C12 C13 C4 0.3(4) C13 N1 C1 C2 1.8(5) C13 N1 C1 Cl1 -179.1(2) N1 C13 C4 C3 -1.1(5) C12 C13 C4 C3 179.1(3) N1 C13 C4 C5 179.6(3) C12 C13 C4 C5 -0.2(5) N1 C1 C2 C3 -1.7(5) Cl1 C1 C2 C3 179.2(2) N1 C1 C2 C14 178.5(3) Cl1 C1 C2 C14 -0.7(5) C11 C12 C7 C8 -0.3(5) C13 C12 C7 C8 179.5(3) C11 C12 C7 C6 -180.0(3) C13 C12 C7 C6 -0.1(4) C1 C2 C3 C4 0.2(5) C14 C2 C3 C4 180.0(3) C13 C4 C3 C2 1.1(5) C5 C4 C3 C2 -179.6(3) C7 C12 C11 C10 0.4(5) C13 C12 C11 C10 -179.5(3) C8 C7 C6 C5 -179.7(4) C12 C7 C6 C5 -0.1(5) C12 C7 C8 C9 0.1(5) C6 C7 C8 C9 179.7(3) C3 C2 C14 Cl2 -93.2(4) C1 C2 C14 Cl2 86.6(4) C7 C8 C9 C10 0.2(6) C7 C6 C5 C4 0.2(6) C3 C4 C5 C6 -179.3(3) C13 C4 C5 C6 0.0(5) C12 C11 C10 C9 -0.1(6) C8 C9 C10 C11 -0.1(6) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131085 2 PubChem 55173437