#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200522.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_2200522 loop_ _publ_author_name 'Jeffrey C. Bryan' 'Richard A. Sachleben' 'Agathe Urvoas' _publ_section_title ; 5,17-Di-tert-butyl-25,27-dihydroxycalix[4]arene ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o781 _journal_page_last o782 _journal_paper_doi 10.1107/S160053680101220X _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C38 H44 O2' _chemical_formula_moiety 'C38 H44 O2' _chemical_formula_sum 'C38 H44 O2' _chemical_formula_weight 532.7 _chemical_name_common ; 5,17-di-tert-butyl-25,27-dihydroxy-calix[4]arene ; _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' _cell_angle_alpha 90 _cell_angle_beta 105.68(8) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.6623(8) _cell_length_b 18.1338(13) _cell_length_c 9.8554(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 100 _cell_measurement_theta_max 14.3 _cell_measurement_theta_min 10.1 _cell_volume 1490.5(6) _computing_cell_refinement CAD-4-PC _computing_data_collection 'CAD-4-PC (Enraf-Nonius, 1993)' _computing_data_reduction 'XCAD4 (Harms, 1995)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'PLATON (Spek, 2001)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Nonius CAD-4' _diffrn_measurement_method \w _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 .014 _diffrn_reflns_av_sigmaI/netI .032 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3130 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.2 _diffrn_standards_decay_% 5 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .071 _exptl_absorpt_correction_type none _exptl_crystal_colour 'colourless ' _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_meas ? _exptl_crystal_description fragment _exptl_crystal_F_000 576 _exptl_crystal_size_max .70 _exptl_crystal_size_mid .41 _exptl_crystal_size_min .30 _refine_diff_density_max .21 _refine_diff_density_min -.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 185 _refine_ls_number_reflns 2618 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all .056 _refine_ls_R_factor_gt .039 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.4494P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .108 _reflns_number_gt 2090 _reflns_number_total 2618 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6037.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_cell_volume 1490.5(2) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2200522 _cod_database_fobs_code 2200522 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z 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 O .0217(6) .0235(6) .0178(6) .0025(4) .0075(4) .0011(4) C1 .0185(7) .0151(7) .0150(7) .0052(6) .0058(6) .0023(6) C2 .0197(7) .0138(7) .0137(7) .0053(6) .0009(6) .0016(6) C3 .0158(7) .0137(7) .0160(7) .0005(6) .0006(6) .0014(6) C4 .0195(8) .0135(7) .0148(7) .0029(6) .0031(6) .0018(5) C5 .0193(8) .0167(7) .0110(7) .0022(6) .0001(6) .0003(5) C6 .0155(7) .0134(7) .0171(7) .0031(6) .0006(6) .0010(6) C7 .0209(8) .0195(8) .0153(7) -.0010(6) .0043(6) .0002(6) C8 .0304(9) .0360(9) .0197(8) .0037(7) .0074(7) .0087(7) C9 .0348(10) .0254(9) .0273(9) -.0050(7) .0173(8) -.0041(7) C10 .0249(8) .0303(9) .0206(8) -.0065(7) .0071(7) -.0013(7) C11 .0186(8) .0209(8) .0096(7) -.0004(6) .0049(6) .0009(6) C12 .0155(7) .0214(8) .0102(7) -.0021(6) .0004(6) -.0013(6) C13 .0168(7) .0207(8) .0116(7) -.0018(6) .0047(6) .0015(6) C14 .0141(7) .0253(8) .0140(7) .0003(6) .0010(6) .0014(6) C15 .0174(8) .0231(8) .0163(8) -.0051(6) .0006(6) -.0022(6) C16 .0229(8) .0177(7) .0157(7) -.0027(6) .0052(6) -.0010(6) C17 .0223(8) .0184(7) .0135(7) .0019(6) .0024(6) -.0017(6) C18 .0169(7) .0209(8) .0165(7) .0018(6) .0029(6) .0013(6) C19 .0384(10) .0304(9) .0281(9) .0042(8) .0189(8) .0085(7) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O .24785(12) .61658(6) .53954(11) .0206(3) Uani . . 1.000 O C1 .34016(17) .62189(8) .44455(15) .0160(4) Uani . . 1.000 C C2 .49191(18) .65422(7) .48621(15) .0164(4) Uani . . 1.000 C C3 .57635(17) .66457(7) .38569(15) .0159(4) Uani . . 1.000 C C4 .51413(17) .64484(7) .24494(15) .0162(4) Uani . . 1.000 C C5 .36333(17) .61112(8) .20863(15) .0164(4) Uani . . 1.000 C C6 .27512(17) .59868(7) .30516(15) .0161(4) Uani . . 1.000 C C7 .60159(18) .66004(8) .13151(15) .0187(4) Uani . . 1.000 C C8 .4971(2) .70988(9) .01731(17) .0286(5) Uani . . 1.000 C C9 .6320(2) .58680(9) .06472(18) .0274(5) Uani . . 1.000 C C10 .76116(19) .69886(9) .19105(17) .0251(5) Uani . . 1.000 C C11 .71823(17) .63838(8) .71049(14) .0162(4) Uani . . 1.000 C C12 .73164(17) .56265(8) .69336(14) .0163(4) Uani . . 1.000 C C13 .86748(17) .52339(8) .76416(14) .0162(4) Uani . . 1.000 C C14 .99230(17) .56221(8) .85580(15) .0183(4) Uani . . 1.000 C C15 .98116(18) .63753(8) .87292(15) .0197(5) Uani . . 1.000 C C16 .84501(18) .67577(8) .80059(15) .0188(4) Uani . . 1.000 C C17 .56603(18) .67929(8) .63652(15) .0185(4) Uani . . 1.000 C C18 .88365(17) .44125(8) .74080(16) .0184(4) Uani . . 1.000 C C19 .2696(2) .55006(9) .62082(18) .0304(5) Uani . . 1.000 C H3 .68030 .68590 .41430 .0190 Uiso calc R 1.000 H H5 .31920 .59600 .11370 .0200 Uiso calc R 1.000 H H8A .39640 .68450 -.02790 .0430 Uiso calc R 1.000 H H8B .55430 .72120 -.05340 .0430 Uiso calc R 1.000 H H8C .47370 .75580 .06030 .0430 Uiso calc R 1.000 H H9A .69670 .55440 .13780 .0410 Uiso calc R 1.000 H H9B .68940 .59640 -.00660 .0410 Uiso calc R 1.000 H H9C .52920 .56290 .02030 .0410 Uiso calc R 1.000 H H10A .74250 .74700 .22900 .0380 Uiso calc R 1.000 H H10B .81450 .70580 .11610 .0380 Uiso calc R 1.000 H H10C .82930 .66880 .26640 .0380 Uiso calc R 1.000 H H12 .64530 .53700 .63140 .0200 Uiso calc R 1.000 H H14 1.08570 .53660 .90680 .0220 Uiso calc R 1.000 H H15 1.06750 .66330 .93470 .0240 Uiso calc R 1.000 H H16 .83860 .72750 .81270 .0230 Uiso calc R 1.000 H H17A .48650 .67260 .69120 .0220 Uiso calc R 1.000 H H17B .59040 .73260 .63590 .0220 Uiso calc R 1.000 H H18A .94210 .43420 .66820 .0220 Uiso calc R 1.000 H H18B .94870 .41880 .82940 .0220 Uiso calc R 1.000 H H19A .24120 .50760 .55750 .0460 Uiso calc R 1.000 H H19B .20050 .55110 .68490 .0460 Uiso calc R 1.000 H H19C .38190 .54600 .67570 .0460 Uiso calc R 1.000 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -8 -1 0 7 3 1 3 4 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O C19 . . 115.01(14) yes O C1 C2 . . 119.92(15) yes O C1 C6 . . 119.19(15) yes C2 C1 C6 . . 120.78(16) no C1 C2 C3 . . 118.74(15) no C1 C2 C17 . . 121.99(16) no C3 C2 C17 . . 119.27(16) no C2 C3 C4 . . 122.50(16) no C3 C4 C5 . . 116.78(16) no C3 C4 C7 . . 123.02(15) no C5 C4 C7 . . 120.18(15) no C4 C5 C6 . . 122.96(15) no C1 C6 C5 . . 118.19(16) no C1 C6 C18 . 3_666 122.00(15) no C5 C6 C18 . 3_666 119.77(15) no C4 C7 C8 . . 109.31(15) no C4 C7 C9 . . 109.40(14) no C4 C7 C10 . . 112.22(14) no C8 C7 C9 . . 109.30(15) no C8 C7 C10 . . 107.76(15) no C9 C7 C10 . . 108.80(16) no C12 C11 C16 . . 118.80(16) no C12 C11 C17 . . 120.95(15) no C16 C11 C17 . . 120.21(15) no C11 C12 C13 . . 122.08(16) no C12 C13 C14 . . 117.93(15) no C12 C13 C18 . . 121.73(15) no C14 C13 C18 . . 120.32(15) no C13 C14 C15 . . 120.61(16) no C14 C15 C16 . . 120.57(16) no C11 C16 C15 . . 120.01(16) no C2 C17 C11 . . 113.98(15) no C6 C18 C13 3_666 . 113.66(15) no C2 C3 H3 . . 119 no C4 C3 H3 . . 119 no C4 C5 H5 . . 119 no C6 C5 H5 . . 119 no C7 C8 H8A . . 109 no C7 C8 H8B . . 109 no C7 C8 H8C . . 109 no H8A C8 H8B . . 109 no H8A C8 H8C . . 109 no H8B C8 H8C . . 109 no C7 C9 H9A . . 109 no C7 C9 H9B . . 109 no C7 C9 H9C . . 109 no H9A C9 H9B . . 109 no H9A C9 H9C . . 109 no H9B C9 H9C . . 109 no C7 C10 H10A . . 109 no C7 C10 H10B . . 109 no C7 C10 H10C . . 109 no H10A C10 H10B . . 109 no H10A C10 H10C . . 109 no H10B C10 H10C . . 109 no C11 C12 H12 . . 119 no C13 C12 H12 . . 119 no C13 C14 H14 . . 120 no C15 C14 H14 . . 120 no C14 C15 H15 . . 120 no C16 C15 H15 . . 120 no C11 C16 H16 . . 120 no C15 C16 H16 . . 120 no C2 C17 H17A . . 109 no C2 C17 H17B . . 109 no C11 C17 H17A . . 109 no C11 C17 H17B . . 109 no H17A C17 H17B . . 108 no C13 C18 H18A . . 109 no C13 C18 H18B . . 109 no H18A C18 H18B . . 108 no C6 C18 H18A 3_666 . 109 no C6 C18 H18B 3_666 . 109 no O C19 H19A . . 109 no O C19 H19B . . 109 no O C19 H19C . . 109 no H19A C19 H19B . . 109 no H19A C19 H19C . . 109 no H19B C19 H19C . . 109 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O C1 . . 1.3891(18) yes O C19 . . 1.432(2) yes C1 C2 . . 1.396(2) no C1 C6 . . 1.401(2) no C2 C3 . . 1.394(2) no C2 C17 . . 1.516(2) no C3 C4 . . 1.392(2) no C4 C5 . . 1.398(2) no C4 C7 . . 1.535(2) no C5 C6 . . 1.390(2) no C6 C18 . 3_666 1.511(2) no C7 C8 . . 1.534(2) no C7 C9 . . 1.536(2) no C7 C10 . . 1.521(2) no C11 C12 . . 1.392(2) no C11 C16 . . 1.388(2) no C11 C17 . . 1.517(2) no C12 C13 . . 1.391(2) no C13 C14 . . 1.397(2) no C13 C18 . . 1.519(2) no C14 C15 . . 1.383(2) no C15 C16 . . 1.388(2) no C3 H3 . . .95 no C5 H5 . . .95 no C8 H8A . . .98 no C8 H8B . . .98 no C8 H8C . . .98 no C9 H9A . . .98 no C9 H9B . . .98 no C9 H9C . . .98 no C10 H10A . . .98 no C10 H10B . . .98 no C10 H10C . . .98 no C12 H12 . . .95 no C14 H14 . . .95 no C15 H15 . . .95 no C16 H16 . . .95 no C17 H17A . . .99 no C17 H17B . . .99 no C18 H18A . . .99 no C18 H18B . . .99 no C19 H19A . . .98 no C19 H19B . . .98 no C19 H19C . . .98 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 C17 H17A O . .9901 2.4227 2.8947(19) 108.59 no C18 H18A O 3_666 .9902 2.4344 2.8861(19) 107.17 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_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C19 O C1 C2 . . -90.54(18) no C19 O C1 C6 . . 93.37(18) no C1 O C19 H19B . . 179.79 no C1 O C19 H19C . . 59.79 no C1 O C19 H19A . . -60.21 no O C1 C2 C3 . . -174.59(15) no O C1 C2 C17 . . 4.5(2) no O C1 C6 C18 . 3_666 -8.3(2) no C2 C1 C6 C5 . . -2.2(2) no C2 C1 C6 C18 . 3_666 175.67(15) no O C1 C6 C5 . . 173.81(15) no C6 C1 C2 C3 . . 1.4(2) no C6 C1 C2 C17 . . -179.47(15) no C1 C2 C3 C4 . . .9(2) no C3 C2 C17 C11 . . -64.25(19) no C1 C2 C17 C11 . . 116.67(17) no C17 C2 C3 C4 . . -178.18(15) no C2 C3 C4 C5 . . -2.3(2) no C2 C3 C4 C7 . . 176.32(15) no C3 C4 C5 C6 . . 1.5(2) no C7 C4 C5 C6 . . -177.22(15) no C3 C4 C7 C8 . . -119.72(17) no C3 C4 C7 C9 . . 120.63(17) no C5 C4 C7 C10 . . 178.37(15) no C3 C4 C7 C10 . . -.2(2) no C5 C4 C7 C8 . . 58.89(19) no C5 C4 C7 C9 . . -60.76(19) no C4 C5 C6 C1 . . .8(2) no C4 C5 C6 C18 . 3_666 -177.20(15) no C1 C6 C18 C13 3_666 3_666 -105.01(17) no C5 C6 C18 C13 3_666 3_666 72.87(19) no C12 C11 C16 C15 . . -.8(2) no C17 C11 C16 C15 . . 177.10(16) no C16 C11 C17 C2 . . 141.71(16) no C17 C11 C12 C13 . . -177.50(16) no C12 C11 C17 C2 . . -40.5(2) no C16 C11 C12 C13 . . .3(2) no C11 C12 C13 C14 . . .6(2) no C11 C12 C13 C18 . . -177.73(16) no C12 C13 C18 C6 . 3_666 -27.0(2) no C12 C13 C14 C15 . . -1.1(2) no C18 C13 C14 C15 . . 177.21(16) no C14 C13 C18 C6 . 3_666 154.73(16) no C13 C14 C15 C16 . . .7(2) no C14 C15 C16 C11 . . .2(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139064928