#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/37/2203725.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_2203725 loop_ _publ_author_name 'Shen-Lin Huang' 'Yu-Lin Zhu' 'Yuan-Jiang Pan' _publ_section_title ; (E)-2-(2-Fluorobenzylidene)cyclooctanone ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1000 _journal_page_last o1002 _journal_paper_doi 10.1107/S1600536804011079 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C15 H17 F O' _chemical_formula_moiety 'C15 H17 F O' _chemical_formula_sum 'C15 H17 F O' _chemical_formula_weight 232.29 _chemical_melting_point '465--466 K' _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.2910(10) _cell_length_b 8.2940(10) _cell_length_c 12.2730(10) _cell_measurement_reflns_used 39 _cell_measurement_temperature 287(2) _cell_measurement_theta_max 14.62 _cell_measurement_theta_min 2.96 _cell_volume 1251.1(2) _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 287(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 0.0094 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1904 _diffrn_reflns_theta_full 27.85 _diffrn_reflns_theta_max 27.85 _diffrn_reflns_theta_min 2.96 _diffrn_standards_decay_% 2.65 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.46 _refine_diff_density_max 0.109 _refine_diff_density_min -0.096 _refine_ls_extinction_coef 0.033(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1560 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.936 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0315 _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^)+(0.0429P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.0731 _reflns_number_gt 1207 _reflns_number_total 1560 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6365.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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: '_chemical_melting_point' value '465--466 K' was changed to '465.5(5)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 1251.2(2) _cod_database_code 2203725 _cod_database_fobs_code 2203725 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' 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 F1 0.74470(11) 0.76983(16) 0.40459(10) 0.0722(4) Uani d . 1 F O1 0.46008(14) 0.37243(18) 0.41115(12) 0.0684(5) Uani d . 1 O C1 0.52979(17) 0.3016(2) 0.35914(16) 0.0461(4) Uani d . 1 C C2 0.5466(2) 0.1227(2) 0.37770(17) 0.0573(6) Uani d . 1 C H2A 0.5406 0.1003 0.4550 0.069 Uiso calc R 1 H H2B 0.6196 0.0938 0.3549 0.069 Uiso calc R 1 H C3 0.4650(2) 0.0181(3) 0.31624(19) 0.0621(6) Uani d . 1 C H3A 0.4708 -0.0913 0.3437 0.075 Uiso calc R 1 H H3B 0.3924 0.0562 0.3334 0.075 Uiso calc R 1 H C4 0.47646(18) 0.0126(2) 0.19302(18) 0.0546(5) Uani d . 1 C H4A 0.4245 -0.0646 0.1646 0.066 Uiso calc R 1 H H4B 0.5487 -0.0268 0.1755 0.066 Uiso calc R 1 H C5 0.45920(16) 0.1737(2) 0.13445(16) 0.0485(5) Uani d . 1 C H5A 0.4126 0.1550 0.0720 0.058 Uiso calc R 1 H H5B 0.4206 0.2456 0.1834 0.058 Uiso calc R 1 H C6 0.56082(18) 0.2586(2) 0.09556(16) 0.0498(5) Uani d . 1 C H6A 0.5395 0.3585 0.0605 0.060 Uiso calc R 1 H H6B 0.5955 0.1917 0.0408 0.060 Uiso calc R 1 H C7 0.64514(13) 0.2979(2) 0.18409(17) 0.0451(4) Uani d . 1 C H7A 0.6763 0.1979 0.2107 0.054 Uiso calc R 1 H H7B 0.7034 0.3606 0.1519 0.054 Uiso calc R 1 H C8 0.59863(13) 0.3901(2) 0.27899(14) 0.0382(4) Uani d . 1 C C9 0.61667(15) 0.5459(2) 0.30104(15) 0.0428(4) Uani d . 1 C H9 0.5837 0.5854 0.3638 0.051 Uiso calc R 1 H C10 0.68198(15) 0.6627(2) 0.23886(15) 0.0407(4) Uani d . 1 C C11 0.68246(16) 0.6746(2) 0.12592(16) 0.0475(5) Uani d . 1 C H11 0.6400 0.6041 0.0852 0.057 Uiso calc R 1 H C12 0.74456(19) 0.7889(3) 0.0728(2) 0.0563(6) Uani d . 1 C H12 0.7431 0.7949 -0.0028 0.068 Uiso calc R 1 H C13 0.8086(2) 0.8937(3) 0.1311(2) 0.0644(6) Uani d . 1 C H13 0.8513 0.9690 0.0948 0.077 Uiso calc R 1 H C14 0.80958(18) 0.8877(3) 0.2435(2) 0.0595(6) Uani d . 1 C H14 0.8523 0.9585 0.2838 0.071 Uiso calc R 1 H C15 0.74594(17) 0.7745(2) 0.29407(17) 0.0492(5) Uani d . 1 C 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 F1 0.0863(9) 0.0736(9) 0.0568(8) -0.0067(7) -0.0207(7) -0.0137(7) O1 0.0921(11) 0.0618(9) 0.0514(9) 0.0018(8) 0.0305(9) 0.0017(8) C1 0.0590(11) 0.0454(10) 0.0341(9) -0.0037(10) -0.0048(10) 0.0026(8) C2 0.0797(14) 0.0466(11) 0.0456(12) -0.0055(11) -0.0047(11) 0.0126(9) C3 0.0805(16) 0.0475(11) 0.0583(14) -0.0167(11) 0.0069(13) 0.0081(10) C4 0.0589(12) 0.0474(11) 0.0576(13) -0.0115(9) 0.0052(11) -0.0044(10) C5 0.0484(10) 0.0531(11) 0.0441(9) -0.0033(10) -0.0037(9) -0.0068(9) C6 0.0616(12) 0.0496(10) 0.0383(9) -0.0050(9) 0.0111(9) -0.0057(9) C7 0.0390(8) 0.0396(9) 0.0568(11) 0.0008(8) 0.0117(10) 0.0020(10) C8 0.0365(9) 0.0391(9) 0.0389(9) 0.0032(7) -0.0060(8) 0.0015(8) C9 0.0486(10) 0.0433(9) 0.0364(9) 0.0030(9) -0.0056(8) -0.0005(8) C10 0.0405(11) 0.0335(10) 0.0482(11) 0.0041(8) -0.0065(9) -0.0017(8) C11 0.0477(11) 0.0432(11) 0.0516(12) -0.0031(10) -0.0063(10) 0.0019(9) C12 0.0577(14) 0.0516(13) 0.0595(13) -0.0006(11) 0.0043(11) 0.0084(10) C13 0.0563(13) 0.0446(12) 0.0923(19) -0.0061(11) 0.0123(13) 0.0042(13) C14 0.0488(12) 0.0428(12) 0.0870(19) -0.0074(10) -0.0085(12) -0.0107(13) C15 0.0484(11) 0.0417(11) 0.0575(13) 0.0043(9) -0.0120(10) -0.0069(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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 '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 O1 C1 C8 120.46(17) y O1 C1 C2 119.27(19) y C8 C1 C2 120.27(18) ? C1 C2 C3 113.17(18) ? C1 C2 H2A 108.9 ? C3 C2 H2A 108.9 ? C1 C2 H2B 108.9 ? C3 C2 H2B 108.9 ? H2A C2 H2B 107.8 ? C4 C3 C2 116.59(19) ? C4 C3 H3A 108.1 ? C2 C3 H3A 108.1 ? C4 C3 H3B 108.1 ? C2 C3 H3B 108.1 ? H3A C3 H3B 107.3 ? C3 C4 C5 115.37(17) ? C3 C4 H4A 108.4 ? C5 C4 H4A 108.4 ? C3 C4 H4B 108.4 ? C5 C4 H4B 108.4 ? H4A C4 H4B 107.5 ? C6 C5 C4 116.11(18) ? 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 115.65(16) ? C5 C6 H6A 108.4 ? C7 C6 H6A 108.4 ? C5 C6 H6B 108.4 ? C7 C6 H6B 108.4 ? H6A C6 H6B 107.4 ? C8 C7 C6 113.48(14) ? C8 C7 H7A 108.9 ? C6 C7 H7A 108.9 ? C8 C7 H7B 108.9 ? C6 C7 H7B 108.9 ? H7A C7 H7B 107.7 ? C9 C8 C1 115.84(17) ? C9 C8 C7 125.70(17) ? C1 C8 C7 118.41(15) ? C8 C9 C10 128.40(17) ? C8 C9 H9 115.8 ? C10 C9 H9 115.8 ? C11 C10 C15 115.85(19) ? C11 C10 C9 124.50(18) ? C15 C10 C9 119.62(17) ? C12 C11 C10 121.5(2) ? C12 C11 H11 119.3 ? C10 C11 H11 119.3 ? C13 C12 C11 120.4(2) ? C13 C12 H12 119.8 ? C11 C12 H12 119.8 ? C12 C13 C14 120.2(2) ? C12 C13 H13 119.9 ? C14 C13 H13 119.9 ? C15 C14 C13 118.2(2) ? C15 C14 H14 120.9 ? C13 C14 H14 120.9 ? F1 C15 C14 118.6(2) ? F1 C15 C10 117.48(19) ? C14 C15 C10 123.9(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag F1 C15 1.357(2) y O1 C1 1.219(2) y C1 C8 1.491(3) y C1 C2 1.515(3) ? C2 C3 1.526(3) ? C2 H2A 0.97 ? C2 H2B 0.97 ? C3 C4 1.520(3) ? C3 H3A 0.97 ? C3 H3B 0.97 ? C4 C5 1.532(3) ? C4 H4A 0.97 ? C4 H4B 0.97 ? C5 C6 1.511(3) ? C5 H5A 0.97 ? C5 H5B 0.97 ? C6 C7 1.537(3) ? C6 H6A 0.97 ? C6 H6B 0.97 ? C7 C8 1.506(3) ? C7 H7A 0.97 ? C7 H7B 0.97 ? C8 C9 1.339(2) y C9 C10 1.472(3) y C9 H9 0.93 ? C10 C11 1.390(2) ? C10 C15 1.391(3) ? C11 C12 1.380(3) ? C11 H11 0.93 ? C12 C13 1.374(3) ? C12 H12 0.93 ? C13 C14 1.380(3) ? C13 H13 0.93 ? C14 C15 1.370(3) ? C14 H14 0.93 ? 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 C11 H11 O1 2_664 0.93 2.47 3.189(3) 134 y C14 H14 O1 3_565 0.93 2.48 3.408(3) 173 y C4 H4A CgP 3_465 0.97 2.85 3.738(3) 153 y C4 H4B CgP 1_545 0.97 2.90 3.829(2) 160 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 O1 C1 C2 C3 81.3(2) ? C8 C1 C2 C3 -99.3(2) y C1 C2 C3 C4 69.8(3) y C2 C3 C4 C5 -63.1(3) y C3 C4 C5 C6 103.5(2) y C4 C5 C6 C7 -57.8(2) y C5 C6 C7 C8 -53.3(2) y O1 C1 C8 C9 29.4(3) ? C2 C1 C8 C9 -149.91(18) ? O1 C1 C8 C7 -152.93(19) ? C2 C1 C8 C7 27.7(2) y C6 C7 C8 C9 -107.7(2) ? C6 C7 C8 C1 74.9(2) y C1 C8 C9 C10 179.00(17) ? C7 C8 C9 C10 1.6(3) ? C8 C9 C10 C11 41.5(3) ? C8 C9 C10 C15 -140.8(2) ? C15 C10 C11 C12 1.2(3) ? C9 C10 C11 C12 179.01(17) ? C10 C11 C12 C13 0.5(3) ? C11 C12 C13 C14 -1.3(4) ? C12 C13 C14 C15 0.4(4) ? C13 C14 C15 F1 -178.7(2) ? C13 C14 C15 C10 1.4(4) ? C11 C10 C15 F1 177.92(18) ? C9 C10 C15 F1 0.0(3) ? C11 C10 C15 C14 -2.2(3) ? C9 C10 C15 C14 179.88(19) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654749 2 PubChem 139066717