#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011315.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_2011315 loop_ _publ_author_name 'Bryan, Jeffrey C.' 'Sachleben, Richard A.' _publ_section_title ; Benzo-cis-cyclohexano-14-crown-4 and its lithium thiocyanate complex ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1104 _journal_page_last 1106 _journal_paper_doi 10.1107/S0108270100009033 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C18 H26 O4' _chemical_formula_structural 'C18 H26 O4' _chemical_formula_sum 'C18 H26 O4' _chemical_formula_weight 306.4 _chemical_name_common benzo,cis-cyclohexano-14-crown-4 _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_type_scat_source ;International Tables for Crystallography (1992, Vol C, Tables 4.2.6.8 and 6.1.1.4) ; _cell_angle_alpha 90.00 _cell_angle_beta 107.841(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.9888(11) _cell_length_b 15.5672(9) _cell_length_c 10.9050(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 163(2) _cell_measurement_theta_max 14.4 _cell_measurement_theta_min 10.1 _cell_volume 1614.2(2) _computing_cell_refinement CAD4-PC _computing_data_collection 'CAD4-PC (Nonius, 1993)' _computing_data_reduction 'XCAD4 (Harms, 1995)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 163(2) _diffrn_measurement_device_type 'Nonius CAD4' _diffrn_measurement_method \w-scans _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .021 _diffrn_reflns_av_sigmaI/netI .033 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4433 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.3 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .088 _exptl_absorpt_correction_T_max .9692 _exptl_absorpt_correction_T_min .9633 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.26 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 664 _exptl_crystal_size_max .43 _exptl_crystal_size_mid .37 _exptl_crystal_size_min .36 _refine_diff_density_max .24 _refine_diff_density_min -.24 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3677 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all .055 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.4290P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .100 _reflns_number_gt 2935 _reflns_number_total 3677 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1290.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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2011315 _cod_database_fobs_code 2011315 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_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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .02977(8) .50591(5) .28511(8) .02213(19) Uani d . 1 . . O C2 .16141(12) .51025(7) .26878(11) .0185(2) Uani d . 1 . . C C3 .27383(12) .46327(7) .34711(11) .0202(2) Uani d . 1 . . C O4 .25162(10) .41149(6) .44142(9) .0268(2) Uani d . 1 . . O C5 .29291(14) .32301(8) .43957(12) .0247(3) Uani d . 1 . . C H5A .3815 .3191 .4171 .030 Uiso calc R 1 . . H H5B .2192 .2906 .3745 .030 Uiso calc R 1 . . H C6 .31347(13) .28578(8) .57208(12) .0249(3) Uani d . 1 . . C H6A .3871 .3191 .6358 .030 Uiso calc R 1 . . H H6B .3474 .2259 .5737 .030 Uiso calc R 1 . . H C7 .18109(13) .28626(8) .61168(11) .0226(3) Uani d . 1 . . C H7A .2023 .2674 .7023 .027 Uiso calc R 1 . . H H7B .1410 .3449 .6038 .027 Uiso calc R 1 . . H O8 .08379(8) .22881(5) .52851(8) .02079(19) Uani d . 1 . . O C9 -.04501(12) .21903(7) .55798(11) .0183(2) Uani d . 1 . . C H9 -.0222 .2016 .6504 .022 Uiso calc R 1 . . H C10 -.13192(12) .30154(7) .53830(11) .0184(2) Uani d . 1 . . C H10 -.0777 .3469 .5980 .022 Uiso calc R 1 . . H O11 -.15526(9) .32837(5) .40792(8) .02013(19) Uani d . 1 . . O C12 -.18412(13) .41780(7) .38833(12) .0222(3) Uani d . 1 . . C H12A -.1084 .4518 .4486 .027 Uiso calc R 1 . . H H12B -.2742 .4319 .4039 .027 Uiso calc R 1 . . H C13 -.19275(12) .43860(8) .25042(12) .0228(3) Uani d . 1 . . C H13A -.2595 .3984 .1922 .027 Uiso calc R 1 . . H H13B -.2306 .4974 .2299 .027 Uiso calc R 1 . . H C14 -.05251(12) .43289(7) .22480(11) .0202(2) Uani d . 1 . . C H14A -.0038 .3790 .2611 .024 Uiso calc R 1 . . H H14B -.0665 .4335 .1309 .024 Uiso calc R 1 . . H C15 .18308(13) .56648(7) .17765(12) .0223(3) Uani d . 1 . . C H15 .1063 .5986 .1245 .027 Uiso calc R 1 . . H C16 .31557(14) .57619(8) .16336(12) .0258(3) Uani d . 1 . . C H16 .3295 .6144 .1004 .031 Uiso calc R 1 . . H C17 .42707(13) .52973(8) .24170(13) .0268(3) Uani d . 1 . . C H17 .5182 .5362 .2327 .032 Uiso calc R 1 . . H C18 .40699(13) .47375(8) .33333(12) .0254(3) Uani d . 1 . . C H18 .4844 .4423 .3870 .031 Uiso calc R 1 . . H C19 -.12567(12) .14622(7) .47504(12) .0208(2) Uani d . 1 . . C H19A -.0685 .0931 .4942 .025 Uiso calc R 1 . . H H19B -.1426 .1604 .3830 .025 Uiso calc R 1 . . H C20 -.26653(13) .13050(8) .49947(13) .0247(3) Uani d . 1 . . C H20A -.3200 .0864 .4386 .030 Uiso calc R 1 . . H H20B -.2491 .1082 .5880 .030 Uiso calc R 1 . . H C21 -.35404(13) .21249(8) .48322(12) .0238(3) Uani d . 1 . . C H21A -.3830 .2304 .3917 .029 Uiso calc R 1 . . H H21B -.4401 .2011 .5075 .029 Uiso calc R 1 . . H C22 -.27063(13) .28478(8) .56684(12) .0216(2) Uani d . 1 . . C H22A -.2505 .2694 .6588 .026 Uiso calc R 1 . . H H22B -.3278 .3379 .5508 .026 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 O1 .0183(4) .0187(4) .0323(5) -.0023(3) .0121(3) -.0061(3) C2 .0184(5) .0156(5) .0234(5) -.0016(4) .0091(4) -.0041(4) C3 .0233(6) .0179(5) .0221(6) -.0009(4) .0109(5) .0008(4) O4 .0361(5) .0209(4) .0301(5) .0082(4) .0201(4) .0086(4) C5 .0279(6) .0192(6) .0315(7) .0059(5) .0157(5) .0046(5) C6 .0187(6) .0250(6) .0297(6) .0012(5) .0054(5) .0075(5) C7 .0225(6) .0243(6) .0206(6) -.0037(5) .0060(5) -.0004(5) O8 .0180(4) .0225(4) .0230(4) -.0009(3) .0081(3) -.0035(3) C9 .0189(5) .0187(5) .0189(5) .0004(4) .0080(4) .0007(4) C10 .0212(6) .0168(5) .0190(5) -.0012(4) .0086(4) -.0024(4) O11 .0269(4) .0141(4) .0211(4) .0006(3) .0098(3) .0010(3) C12 .0226(6) .0146(5) .0327(6) .0026(4) .0132(5) .0027(5) C13 .0172(5) .0203(6) .0303(6) .0018(4) .0064(5) .0056(5) C14 .0210(6) .0166(5) .0237(6) -.0021(4) .0078(5) -.0018(4) C15 .0256(6) .0181(5) .0234(6) .0020(5) .0075(5) .0007(4) C16 .0336(7) .0205(6) .0285(6) -.0032(5) .0170(5) .0021(5) C17 .0222(6) .0272(6) .0349(7) -.0050(5) .0145(5) -.0012(5) C18 .0184(6) .0285(6) .0287(6) .0020(5) .0060(5) .0028(5) C19 .0227(6) .0154(5) .0256(6) .0016(4) .0094(5) -.0013(4) C20 .0265(6) .0183(6) .0317(6) -.0043(5) .0124(5) -.0033(5) C21 .0194(6) .0246(6) .0293(6) -.0017(5) .0104(5) -.0011(5) C22 .0236(6) .0200(6) .0249(6) .0014(5) .0129(5) -.0014(5) loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -1 -4 5 2 -3 2 9 -1 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 C2 O1 C14 114.38(8) no O1 C2 C15 119.06(10) no O1 C2 C3 121.06(10) no C15 C2 C3 119.77(11) no O4 C3 C2 118.78(10) no O4 C3 C18 121.78(11) no C2 C3 C18 119.32(11) no C3 O4 C5 115.92(9) no O4 C5 C6 108.00(10) no C5 C6 C7 113.37(10) no O8 C7 C6 107.52(10) no C7 O8 C9 114.22(8) no O8 C9 C19 107.22(9) no O8 C9 C10 113.04(9) no C19 C9 C10 111.64(9) no O11 C10 C9 107.31(9) no O11 C10 C22 111.68(9) no C9 C10 C22 109.78(9) no C12 O11 C10 113.47(9) no O11 C12 C13 107.78(10) no C14 C13 C12 113.36(10) no O1 C14 C13 107.51(9) no C16 C15 C2 120.78(11) no C17 C16 C15 119.29(11) no C16 C17 C18 120.50(11) no C17 C18 C3 120.34(11) no C9 C19 C20 111.35(9) no C21 C20 C19 111.76(10) no C22 C21 C20 111.04(10) no C21 C22 C10 111.49(9) no O4 C5 H5A 110 no O4 C5 H5B 110 no C6 C5 H5A 110 no C6 C5 H5B 110 no H5A C5 H5B 108 no C5 C6 H6A 109 no C5 C6 H6B 109 no C7 C6 H6A 109 no C7 C6 H6B 109 no H6A C6 H6B 108 no O8 C7 H7A 110 no O8 C7 H7B 110 no C6 C7 H7A 110 no C6 C7 H7B 110 no H7A C7 H7B 108 no O8 C9 H9 108 no C10 C9 H9 108 no C19 C9 H9 108 no O11 C10 H10 109 no C9 C10 H10 109 no C22 C10 H10 109 no O11 C12 H12A 110 no O11 C12 H12B 110 no C13 C12 H12A 110 no C13 C12 H12B 110 no H12A C12 H12B 108 no C12 C13 H13A 109 no C12 C13 H13B 109 no C14 C13 H13A 109 no C14 C13 H13B 109 no H13A C13 H13B 108 no O1 C14 H14A 110 no O1 C14 H14B 110 no C13 C14 H14A 110 no C13 C14 H14B 110 no H14A C14 H14B 108 no C2 C15 H15 120 no C16 C15 H15 120 no C15 C16 H16 120 no C17 C16 H16 120 no C16 C17 H17 120 no C18 C17 H17 120 no C3 C18 H18 120 no C17 C18 H18 120 no C9 C19 H19A 109 no C9 C19 H19B 109 no C20 C19 H19A 109 no C20 C19 H19B 109 no H19A C19 H19B 108 no C19 C20 H20A 109 no C19 C20 H20B 109 no C21 C20 H20A 109 no C21 C20 H20B 109 no H20A C20 H20B 108 no C20 C21 H21A 109 no C20 C21 H21B 109 no C22 C21 H21A 109 no C22 C21 H21B 109 no H21A C21 H21B 108 no C10 C22 H22A 109 no C10 C22 H22B 109 no C21 C22 H22A 109 no C21 C22 H22B 109 no H22A C22 H22B 108 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 . 1.3815(13) no O1 C14 . 1.4384(13) no C2 C15 . 1.3902(16) no C2 C3 . 1.3920(16) no C3 O4 . 1.3772(14) no C3 C18 . 1.3932(16) no O4 C5 . 1.4398(14) no C5 C6 . 1.5114(17) no C6 C7 . 1.5116(16) no C7 O8 . 1.4237(14) no O8 C9 . 1.4266(13) no C9 C19 . 1.5183(16) no C9 C10 . 1.5282(16) no C10 O11 . 1.4308(13) no C10 C22 . 1.5326(15) no O11 C12 . 1.4244(13) no C12 C13 . 1.5148(17) no C13 C14 . 1.5127(15) no C15 C16 . 1.3874(17) no C16 C17 . 1.3822(19) no C17 C18 . 1.3860(18) no C19 C20 . 1.5298(16) no C20 C21 . 1.5262(17) no C21 C22 . 1.5254(17) no C5 H5A . .99 no C5 H5B . .99 no C6 H6A . .99 no C6 H6B . .99 no C7 H7A . .99 no C7 H7B . .99 no C9 H9 . 1.00 no C10 H10 . 1.00 no C12 H12A . .99 no C12 H12B . .99 no C13 H13A . .99 no C13 H13B . .99 no C14 H14A . .99 no C14 H14B . .99 no C15 H15 . .95 no C16 H16 . .95 no C17 H17 . .95 no C18 H18 . .95 no C19 H19A . .99 no C19 H19B . .99 no C20 H20A . .99 no C20 H20B . .99 no C21 H21A . .99 no C21 H21B . .99 no C22 H22A . .99 no C22 H22B . .99 no 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 C7 H7B O4 . .99 2.57 2.9233(16) 100 no C10 H10 O1 3_566 1.00 2.59 3.5398(14) 158 no C16 H16 O8 2_555 .95 2.58 3.5103(16) 167 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 _geom_torsion_publ_flag O1 C2 C3 O4 .43(17) yes C2 C3 O4 C5 126.08(12) yes C3 O4 C5 C6 158.82(10) yes O4 C5 C6 C7 61.93(14) yes C5 C6 C7 O8 66.15(13) yes C6 C7 O8 C9 177.12(9) yes C7 O8 C9 C10 65.24(12) yes O8 C9 C10 O11 56.26(12) yes C9 C10 O11 C12 -156.68(9) yes C10 O11 C12 C13 174.72(9) yes O11 C12 C13 C14 -69.43(13) yes C12 C13 C14 O1 -73.07(12) yes C13 C14 O1 C2 -179.30(9) yes C14 O1 C2 C3 -82.11(13) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 101083254