#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204245.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_2204245 loop_ _publ_author_name 'Shen-Lin Huang' 'Yu-Lin Zhu' 'Yuan-Jiang Pan' _publ_section_title ; (E)-2-(4-Chlorobenzylidene)cyclooctanone ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1504 _journal_page_last o1506 _journal_paper_doi 10.1107/S1600536804017994 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C15 H17 Cl O' _chemical_formula_moiety 'C15 H17 Cl O' _chemical_formula_sum 'C15 H17 Cl O' _chemical_formula_weight 248.74 _chemical_melting_point .362E-305 _chemical_name_systematic ; (E)-2-(4-Chlorobenzylidene)cyclooctanone ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 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 100.223(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.4740(10) _cell_length_b 10.5450(10) _cell_length_c 8.5680(10) _cell_measurement_reflns_used 34 _cell_measurement_temperature 288(2) _cell_measurement_theta_max 15.16 _cell_measurement_theta_min 2.76 _cell_volume 664.55(14) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction 'SHELXTL (Siemens, 1991)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 288(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3675 _diffrn_reflns_theta_full 27.70 _diffrn_reflns_theta_max 27.70 _diffrn_reflns_theta_min 2.42 _diffrn_standards_decay_% 3.5 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SHELXTL; Siemens, 1991)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.141 _refine_diff_density_min -0.112 _refine_ls_abs_structure_details '1473 Friedel pairs (Flack, 1983)' _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_extinction_coef 0.056(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 3115 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.961 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0356 _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^)+(0.0378P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0755 _refine_ls_wR_factor_ref 0.0790 _reflns_number_gt 2310 _reflns_number_total 3115 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6265.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_cell_volume 664.60(10) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2204245 _cod_database_fobs_code 2204245 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -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_refinement_flags _atom_site_occupancy _atom_site_type_symbol Cl 0.31690(7) 0.65545(6) 1.17777(6) 0.06703(19) Uani d . 1 Cl O 1.14291(19) 0.38191(16) 0.66331(17) 0.0743(5) Uani d . 1 O C1 1.0234(3) 0.4371(2) 0.5745(2) 0.0502(5) Uani d . 1 C C2 1.0529(3) 0.4676(2) 0.4086(2) 0.0567(5) Uani d . 1 C H2A 0.9735 0.5370 0.3669 0.068 Uiso calc R 1 H H2B 1.1774 0.4956 0.4133 0.068 Uiso calc R 1 H C3 1.0170(3) 0.3563(3) 0.2968(3) 0.0674(6) Uani d . 1 C H3A 1.0842 0.2839 0.3466 0.081 Uiso calc R 1 H H3B 1.0654 0.3762 0.2018 0.081 Uiso calc R 1 H C4 0.8190(3) 0.3175(2) 0.2473(3) 0.0703(7) Uani d . 1 C H4A 0.8127 0.2499 0.1697 0.084 Uiso calc R 1 H H4B 0.7520 0.3891 0.1953 0.084 Uiso calc R 1 H C5 0.7242(3) 0.2727(2) 0.3813(3) 0.0724(7) Uani d . 1 C H5A 0.6553 0.1968 0.3462 0.087 Uiso calc R 1 H H5B 0.8167 0.2492 0.4709 0.087 Uiso calc R 1 H C6 0.5963(3) 0.3678(3) 0.4385(2) 0.0655(6) Uani d . 1 C H6A 0.5410 0.3274 0.5199 0.079 Uiso calc R 1 H H6B 0.4996 0.3874 0.3505 0.079 Uiso calc R 1 H C7 0.6829(3) 0.4929(2) 0.5055(2) 0.0536(5) Uani d . 1 C H7A 0.7123 0.5432 0.4187 0.064 Uiso calc R 1 H H7B 0.5943 0.5400 0.5525 0.064 Uiso calc R 1 H C8 0.8519(2) 0.47659(18) 0.6278(2) 0.0426(4) Uani d . 1 C C9 0.8657(2) 0.50057(19) 0.7830(2) 0.0472(5) Uani d . 1 C H9 0.9815 0.4899 0.8425 0.057 Uiso calc R 1 H C10 0.7261(2) 0.54116(17) 0.87409(19) 0.0416(4) Uani d . 1 C C11 0.5519(2) 0.4895(2) 0.8489(2) 0.0465(4) Uani d . 1 C H11 0.5190 0.4308 0.7679 0.056 Uiso calc R 1 H C12 0.4270(3) 0.52420(19) 0.9427(2) 0.0486(5) Uani d . 1 C H12 0.3115 0.4883 0.9262 0.058 Uiso calc R 1 H C13 0.4759(3) 0.61224(18) 1.0603(2) 0.0455(5) Uani d . 1 C C14 0.6459(3) 0.6660(2) 1.0892(2) 0.0500(4) Uani d . 1 C H14 0.6767 0.7259 1.1692 0.060 Uiso calc R 1 H C15 0.7705(2) 0.62858(18) 0.9957(2) 0.0483(5) Uani d . 1 C H15 0.8869 0.6631 1.0152 0.058 Uiso calc R 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 Cl 0.0666(3) 0.0807(4) 0.0601(3) 0.0020(3) 0.0284(2) -0.0054(3) O 0.0540(8) 0.1060(14) 0.0584(9) 0.0241(9) -0.0023(7) -0.0089(9) C1 0.0475(11) 0.0552(12) 0.0460(10) -0.0015(10) 0.0030(9) -0.0089(9) C2 0.0540(11) 0.0627(14) 0.0575(12) -0.0080(10) 0.0213(9) -0.0051(11) C3 0.0759(15) 0.0748(15) 0.0552(13) 0.0030(13) 0.0217(11) -0.0133(12) C4 0.0839(16) 0.0735(16) 0.0529(12) -0.0070(13) 0.0109(11) -0.0173(12) C5 0.0849(17) 0.0661(15) 0.0643(13) -0.0249(14) 0.0083(12) -0.0109(12) C6 0.0503(11) 0.0957(18) 0.0480(11) -0.0117(12) 0.0016(9) -0.0041(12) C7 0.0493(11) 0.0683(14) 0.0427(10) 0.0102(11) 0.0065(9) 0.0089(10) C8 0.0413(9) 0.0433(11) 0.0427(10) -0.0009(9) 0.0055(8) 0.0023(8) C9 0.0386(9) 0.0555(12) 0.0451(10) 0.0001(9) 0.0014(8) -0.0006(9) C10 0.0423(10) 0.0454(11) 0.0355(9) 0.0001(9) 0.0027(8) 0.0035(8) C11 0.0464(10) 0.0513(11) 0.0399(9) -0.0032(9) 0.0027(8) -0.0057(9) C12 0.0437(10) 0.0529(12) 0.0479(10) -0.0037(9) 0.0051(8) -0.0007(10) C13 0.0479(10) 0.0505(12) 0.0390(9) 0.0063(9) 0.0105(8) 0.0064(8) C14 0.0591(11) 0.0477(11) 0.0420(9) -0.0035(11) 0.0061(8) -0.0047(10) C15 0.0429(10) 0.0563(14) 0.0445(9) -0.0101(9) 0.0041(8) 0.0007(9) 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 _geom_angle_publ_flag O C1 C8 121.19(18) y O C1 C2 118.48(18) y C8 C1 C2 120.32(17) ? C3 C2 C1 113.11(18) ? C3 C2 H2A 109.0 ? C1 C2 H2A 109.0 ? C3 C2 H2B 109.0 ? C1 C2 H2B 109.0 ? H2A C2 H2B 107.8 ? C2 C3 C4 116.18(18) ? C2 C3 H3A 108.2 ? C4 C3 H3A 108.2 ? C2 C3 H3B 108.2 ? C4 C3 H3B 108.2 ? H3A C3 H3B 107.4 ? C3 C4 C5 115.57(18) ? C3 C4 H4A 108.4 ? C5 C4 H4A 108.4 ? C3 C4 H4B 108.4 ? C5 C4 H4B 108.4 ? H4A C4 H4B 107.4 ? C6 C5 C4 116.1(2) ? C6 C5 H5A 108.3 ? C4 C5 H5A 108.3 ? C6 C5 H5B 108.3 ? C4 C5 H5B 108.3 ? H5A C5 H5B 107.4 ? C5 C6 C7 116.01(16) ? C5 C6 H6A 108.3 ? C7 C6 H6A 108.3 ? C5 C6 H6B 108.3 ? C7 C6 H6B 108.3 ? H6A C6 H6B 107.4 ? C8 C7 C6 114.15(18) ? C8 C7 H7A 108.7 ? C6 C7 H7A 108.7 ? C8 C7 H7B 108.7 ? C6 C7 H7B 108.7 ? H7A C7 H7B 107.6 ? C9 C8 C1 115.92(15) ? C9 C8 C7 125.33(17) ? C1 C8 C7 118.67(16) ? C8 C9 C10 130.09(16) ? C8 C9 H9 115.0 ? C10 C9 H9 115.0 ? C15 C10 C11 118.01(16) ? C15 C10 C9 119.56(16) ? C11 C10 C9 122.33(17) ? C12 C11 C10 120.97(18) ? C12 C11 H11 119.5 ? C10 C11 H11 119.5 ? C13 C12 C11 119.06(18) ? C13 C12 H12 120.5 ? C11 C12 H12 120.5 ? C12 C13 C14 122.02(18) ? C12 C13 Cl 118.64(16) ? C14 C13 Cl 119.34(15) ? C13 C14 C15 118.17(18) ? C13 C14 H14 120.9 ? C15 C14 H14 120.9 ? C10 C15 C14 121.75(17) ? C10 C15 H15 119.1 ? C14 C15 H15 119.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl C13 1.7489(18) y O C1 1.214(2) y C1 C8 1.494(3) y C1 C2 1.512(3) ? C2 C3 1.508(3) ? C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 C4 1.522(3) ? C3 H3A 0.9700 ? C3 H3B 0.9700 ? C4 C5 1.527(3) ? C4 H4A 0.9700 ? C4 H4B 0.9700 ? C5 C6 1.525(3) ? C5 H5A 0.9700 ? C5 H5B 0.9700 ? C6 C7 1.536(3) ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 C8 1.501(2) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 C9 1.339(2) y C9 C10 1.474(2) y C9 H9 0.9300 ? C10 C15 1.387(2) ? C10 C11 1.392(3) ? C11 C12 1.385(3) ? C11 H11 0.9300 ? C12 C13 1.371(3) ? C12 H12 0.9300 ? C13 C14 1.373(3) ? C14 C15 1.389(2) ? C14 H14 0.9300 ? C15 H15 0.9300 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C14 H14 O 2_757 0.93 2.43 3.314(3) 159 y C4 H4B Cg 1_554 0.97 2.87 3.806(8) 164 y C5 H5A Cg 2_646 0.97 3.27 4.065000 141 y 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 _geom_torsion_publ_flag O C1 C2 C3 80.4(2) ? C8 C1 C2 C3 -100.7(2) y C1 C2 C3 C4 71.2(3) y C2 C3 C4 C5 -62.5(3) y C3 C4 C5 C6 102.7(3) y C4 C5 C6 C7 -60.5(3) y C5 C6 C7 C8 -49.9(3) y O C1 C8 C9 28.5(3) ? C2 C1 C8 C9 -150.33(18) ? O C1 C8 C7 -154.6(2) ? C2 C1 C8 C7 26.5(3) y C6 C7 C8 C9 -109.6(2) ? C6 C7 C8 C1 73.9(2) y C1 C8 C9 C10 179.84(19) ? C7 C8 C9 C10 3.2(3) ? C8 C9 C10 C15 -141.3(2) ? C8 C9 C10 C11 42.4(3) ? C15 C10 C11 C12 -0.1(3) ? C9 C10 C11 C12 176.17(17) ? C10 C11 C12 C13 1.0(3) ? C11 C12 C13 C14 -0.8(3) ? C11 C12 C13 Cl 179.92(15) ? C12 C13 C14 C15 -0.2(3) ? Cl C13 C14 C15 179.03(14) ? C11 C10 C15 C14 -1.0(3) ? C9 C10 C15 C14 -177.36(18) ? C13 C14 C15 C10 1.1(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654763 2 PubChem 12682640