#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200590.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_2200590 loop_ _publ_author_name 'Onoda, Akira' 'Okamura, Taka-aki' 'Yamamoto, Hitoshi' 'Ueyama, Norikazu' _publ_section_title ; One-dimensional P--OH···O=P hydrogen bonds restricted by the bulky molecule 2,6-diisopropylphenyl dihydrogen phosphate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1022 _journal_page_last o1024 _journal_paper_doi 10.1107/S160053680101635X _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C12 H19 O4 P' _chemical_formula_moiety 'C12 H19 O4 P' _chemical_formula_sum 'C12 H19 O4 P' _chemical_formula_weight 258.24 _chemical_name_common '2,6-diisopropylbenzene phosphoric acid' _chemical_name_systematic ; 2,6-Diisopropylbenzene dihydrogen phosphate ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.685(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 10.0298(15) _cell_length_b 6.3718(15) _cell_length_c 11.2238(14) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 14.7 _cell_volume 704.9(2) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1999)' _computing_molecular_graphics TEXSAN _computing_publication_material TEXSAN _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Rigaku AFC-5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .0138 _diffrn_reflns_av_sigmaI/netI .0305 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2329 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.50 _diffrn_standards_decay_% .73 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .196 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 276 _exptl_crystal_size_max .300 _exptl_crystal_size_mid .200 _exptl_crystal_size_min .200 _refine_diff_density_max .239 _refine_diff_density_min -.247 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack .11(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 2219 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all .0667 _refine_ls_R_factor_gt .0347 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0527P)^2^+0.1189P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1057 _reflns_number_gt 1627 _reflns_number_total 2219 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6070.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (4 times). '_geom_angle_publ_flag' value 'Yes' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (7 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2200590 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol P1 .12980(6) .50000(10) .02135(6) .03514(14) Uani d . 1 . . P O1 .24004(17) .3911(3) .11897(16) .0402(4) Uani d . 1 . . O O2 .1299(2) .3641(4) -.09264(16) .0459(5) Uani d . 1 . . O H1 .0922 .2520 -.0853 .055 Uiso calc R 1 . . H O3 -.00615(15) .5133(4) .05675(15) .0393(4) Uani d . 1 . . O O4 .18713(18) .7165(3) -.0045(2) .0495(5) Uani d . 1 . . O H2 .1243 .7980 -.0272 .059 Uiso calc R 1 . . H C1 .2765(3) .4642(5) .2409(2) .0426(7) Uani d . 1 . . C C2 .3916(3) .5918(6) .2681(3) .0534(7) Uani d . 1 . . C C3 .4267(4) .6547(7) .3889(3) .0722(11) Uani d . 1 . . C H3 .5032 .7382 .4123 .087 Uiso calc R 1 . . H C4 .3524(4) .5976(9) .4740(3) .0772(12) Uani d . 1 . . C H4 .3760 .6477 .5529 .093 Uiso calc R 1 . . H C5 .2430(4) .4666(8) .4432(3) .0683(11) Uani d . 1 . . C H5 .1947 .4265 .5026 .082 Uiso calc R 1 . . H C6 .2021(3) .3919(5) .3256(3) .0489(7) Uani d . 1 . . C C7 .0894(3) .2318(6) .2952(3) .0557(8) Uani d . 1 . . C H6 .0696 .2165 .2068 .067 Uiso calc R 1 . . H C8 .1357(5) .0171(9) .3487(4) .0913(13) Uani d . 1 . . C H7 .2126 -.0294 .3160 .110 Uiso calc R 1 . . H H8 .0631 -.0821 .3283 .110 Uiso calc R 1 . . H H9 .1605 .0283 .4353 .110 Uiso calc R 1 . . H C9 -.0412(4) .3002(11) .3344(4) .0979(17) Uani d . 1 . . C H10 -.0244 .3225 .4205 .117 Uiso calc R 1 . . H H11 -.1088 .1930 .3138 .117 Uiso calc R 1 . . H H12 -.0730 .4283 .2938 .117 Uiso calc R 1 . . H C10 .4776(3) .6500(7) .1756(4) .0652(9) Uani d . 1 . . C H13 .4275 .6074 .0959 .078 Uiso calc R 1 . . H C11 .6099(4) .5235(14) .2002(5) .123(2) Uani d . 1 . . C H14 .6618 .5532 .1383 .147 Uiso calc R 1 . . H H15 .5893 .3764 .1997 .147 Uiso calc R 1 . . H H16 .6617 .5618 .2779 .147 Uiso calc R 1 . . H C12 .5022(6) .8825(10) .1704(5) .1106(19) Uani d . 1 . . C H17 .5508 .9298 .2476 .133 Uiso calc R 1 . . H H18 .4169 .9546 .1514 .133 Uiso calc R 1 . . H H19 .5548 .9115 .1090 .133 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 P1 .0326(2) .0288(2) .0447(3) .0002(3) .0091(2) .0030(3) O1 .0358(8) .0375(10) .0473(10) .0068(8) .0076(7) .0016(8) O2 .0539(11) .0419(11) .0453(10) -.0028(10) .0182(8) .0003(9) O3 .0332(7) .0328(8) .0533(9) .0009(10) .0117(6) .0017(10) O4 .0357(9) .0335(10) .0795(14) -.0028(8) .0114(9) .0118(10) C1 .0434(12) .0427(19) .0402(12) .0122(11) .0041(9) .0031(11) C2 .0433(15) .0496(16) .0622(18) .0025(13) -.0033(13) .0018(16) C3 .069(2) .067(3) .069(2) .000(2) -.0191(18) -.006(2) C4 .102(3) .075(3) .0442(17) .012(2) -.0115(19) -.0050(18) C5 .086(2) .074(3) .0443(15) .021(2) .0106(15) .0085(17) C6 .0535(15) .0461(17) .0482(14) .0161(14) .0121(12) .0120(14) C7 .0588(18) .0551(18) .0564(17) .0039(16) .0189(14) .0158(16) C8 .112(3) .067(3) .093(3) .004(3) .014(2) .028(3) C9 .068(2) .122(5) .113(3) .007(3) .041(2) .007(4) C10 .0419(15) .069(2) .081(2) -.0087(17) .0026(15) .001(2) C11 .058(2) .131(6) .186(5) .019(4) .039(3) .037(5) C12 .131(5) .085(4) .117(4) -.022(4) .029(4) .017(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P .1023 .0942 '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 O3 P1 O4 112.98(12) yes O3 P1 O2 113.17(11) yes O4 P1 O2 106.75(12) yes O3 P1 O1 113.60(10) yes O4 P1 O1 106.74(11) yes O2 P1 O1 102.83(11) yes C1 O1 P1 123.23(16) yes P1 O2 H1 109.5 ? P1 O4 H2 109.5 ? C6 C1 C2 124.6(3) ? C6 C1 O1 118.2(3) ? C2 C1 O1 117.0(2) ? C3 C2 C1 115.4(3) ? C3 C2 C10 121.5(3) ? C1 C2 C10 123.0(3) ? C4 C3 C2 122.1(4) ? C4 C3 H3 119.0 ? C2 C3 H3 119.0 ? C3 C4 C5 120.1(3) ? C3 C4 H4 119.9 ? C5 C4 H4 119.9 ? C4 C5 C6 121.9(3) ? C4 C5 H5 119.1 ? C6 C5 H5 119.1 ? C5 C6 C1 115.7(3) ? C5 C6 C7 121.4(3) ? C1 C6 C7 122.8(3) ? C6 C7 C9 112.9(4) ? C6 C7 C8 110.7(3) ? C9 C7 C8 111.0(4) ? C6 C7 H6 107.3 ? C9 C7 H6 107.3 ? C8 C7 H6 107.3 ? C7 C8 H7 109.5 ? C7 C8 H8 109.5 ? H7 C8 H8 109.5 ? C7 C8 H9 109.5 ? H7 C8 H9 109.5 ? H8 C8 H9 109.5 ? C7 C9 H10 109.5 ? C7 C9 H11 109.5 ? H10 C9 H11 109.5 ? C7 C9 H12 109.5 ? H10 C9 H12 109.5 ? H11 C9 H12 109.5 ? C12 C10 C2 112.7(4) ? C12 C10 C11 112.4(5) ? C2 C10 C11 109.4(4) ? C12 C10 H13 107.3 ? C2 C10 H13 107.3 ? C11 C10 H13 107.3 ? C10 C11 H14 109.5 ? C10 C11 H15 109.5 ? H14 C11 H15 109.5 ? C10 C11 H16 109.5 ? H14 C11 H16 109.5 ? H15 C11 H16 109.5 ? C10 C12 H17 109.5 ? C10 C12 H18 109.5 ? H17 C12 H18 109.5 ? C10 C12 H19 109.5 ? H17 C12 H19 109.5 ? H18 C12 H19 109.5 ? 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 P1 O3 . 1.4917(16) yes P1 O4 . 1.543(2) yes P1 O2 . 1.545(2) yes P1 O1 . 1.5668(18) yes O1 C1 . 1.427(3) ? O2 H1 . .8200 ? O4 H2 . .8200 ? C1 C6 . 1.392(4) ? C1 C2 . 1.399(4) ? C2 C3 . 1.395(5) ? C2 C10 . 1.513(5) ? C3 C4 . 1.365(6) ? C3 H3 . .9300 ? C4 C5 . 1.371(6) ? C4 H4 . .9300 ? C5 C6 . 1.391(5) ? C5 H5 . .9300 ? C6 C7 . 1.514(5) ? C7 C9 . 1.521(5) ? C7 C8 . 1.531(6) ? C7 H6 . .9800 ? C8 H7 . .9600 ? C8 H8 . .9600 ? C8 H9 . .9600 ? C9 H10 . .9600 ? C9 H11 . .9600 ? C9 H12 . .9600 ? C10 C12 . 1.505(8) ? C10 C11 . 1.534(7) ? C10 H13 . .9800 ? C11 H14 . .9600 ? C11 H15 . .9600 ? C11 H16 . .9600 ? C12 H17 . .9600 ? C12 H18 . .9600 ? C12 H19 . .9600 ? 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 O2 H1 O3 2_545 .82 1.81 2.624(3) 175.1 O4 H2 O3 2 .82 1.80 2.611(3) 168.6 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 O3 P1 O1 C1 -57.8(2) O4 P1 O1 C1 67.4(2) O2 P1 O1 C1 179.56(19) P1 O1 C1 C6 87.5(3) P1 O1 C1 C2 -97.2(3) C6 C1 C2 C3 -3.0(5) O1 C1 C2 C3 -178.0(3) C6 C1 C2 C10 173.9(3) O1 C1 C2 C10 -1.1(5) C1 C2 C3 C4 -.9(6) C10 C2 C3 C4 -177.9(4) C2 C3 C4 C5 3.1(7) C3 C4 C5 C6 -1.5(7) C4 C5 C6 C1 -2.1(5) C4 C5 C6 C7 174.3(4) C2 C1 C6 C5 4.4(5) O1 C1 C6 C5 179.4(3) C2 C1 C6 C7 -171.9(3) O1 C1 C6 C7 3.0(4) C5 C6 C7 C9 54.5(4) C1 C6 C7 C9 -129.4(3) C5 C6 C7 C8 -70.6(4) C1 C6 C7 C8 105.5(4) C3 C2 C10 C12 -54.1(5) C1 C2 C10 C12 129.1(4) C3 C2 C10 C11 71.8(5) C1 C2 C10 C11 -105.0(5) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 3302111 2 PubChem 4087619