#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011509.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_2011509 loop_ _publ_author_name 'Madhavi, N. N. Laxmi' 'Desiraju, Gautam R.' 'Bilton, Clair' 'Howard, Judith A.K.' 'Allen, Frank H.' _publ_section_title ; Racemic 1,2-diphenylbut-3-yn-2-ol ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1359 _journal_page_last 1360 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C16 H14 O' _chemical_formula_sum 'C16 H14 O' _chemical_formula_weight 222.27 _chemical_name_systematic ; 1,2-Diphenylbut-3-yn-2-ol ; _space_group_IT_number 81 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall 'P -4' _symmetry_space_group_name_H-M 'P -4' _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 19.8403(4) _cell_length_b 19.8403(4) _cell_length_c 6.5068(2) _cell_measurement_reflns_used 999 _cell_measurement_temperature 150 _cell_measurement_theta_max 22.42 _cell_measurement_theta_min 10.21 _cell_volume 2561.32(11) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics SHELXL97 _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150 _diffrn_detector_area_resol_mean 'not relevant' _diffrn_measured_fraction_theta_full .937 _diffrn_measured_fraction_theta_max .937 _diffrn_measurement_device_type 'Bruker SMART CCD' _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 .024 _diffrn_reflns_av_sigmaI/netI .026 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 20665 _diffrn_reflns_theta_full 30.35 _diffrn_reflns_theta_max 30.35 _diffrn_reflns_theta_min 1.03 _exptl_absorpt_coefficient_mu .070 _exptl_absorpt_correction_T_max .979 _exptl_absorpt_correction_T_min .907 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(XPREP in SHELXL97; Sheldrick, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max .4 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .3 _refine_diff_density_max .24 _refine_diff_density_min -.20 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 419 _refine_ls_number_reflns 7018 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all .045 _refine_ls_R_factor_gt .037 _refine_ls_shift/su_max .010 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.1122P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .092 _reflns_number_gt 6166 _reflns_number_total 7018 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1108.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M P-4 _cod_database_code 2011509 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -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 C1 .21822(7) .46964(7) .8364(3) .0392(3) Uani d . 1 . . C H1 .2509(9) .5052(9) .900(3) .041(4) Uiso d . 1 . . H C2 .16227(8) .44983(8) .9514(3) .0527(4) Uani d . 1 . . C H2 .1552(11) .4713(11) 1.092(4) .068(6) Uiso d . 1 . . H C3 .11804(8) .40265(9) .8754(4) .0603(6) Uani d . 1 . . C H3 .0769(13) .3921(12) .957(4) .082(7) Uiso d . 1 . . H O17 .41054(4) .45812(4) .46004(12) .02360(16) Uani d . 1 . . O H17 .4465(10) .4396(10) .490(3) .050(5) Uiso d . 1 . . H C4 .12970(8) .37424(9) .6856(4) .0602(6) Uani d . 1 . . C H4 .0965(13) .3396(13) .637(4) .087(7) Uiso d . 1 . . H C5 .18615(7) .39275(8) .5693(3) .0438(4) Uani d . 1 . . C H5 .1923(10) .3747(10) .437(4) .057(6) Uiso d . 1 . . H C6 .23112(6) .44083(6) .6444(2) .0307(3) Uani d . 1 . . C C7 .29237(6) .46152(6) .5211(2) .0264(2) Uani d . 1 . . C H7A .2855(8) .4480(8) .379(3) .034(4) Uiso d . 1 . . H H7B .2982(7) .5097(7) .533(2) .020(3) Uiso d . 1 . . H C8 .35937(5) .42824(6) .59185(17) .0217(2) Uani d . 1 . . C C9 .35902(5) .35153(6) .56278(19) .0232(2) Uani d . 1 . . C C10 .36906(7) .30716(6) .7265(2) .0313(3) Uani d . 1 . . C H10 .3740(8) .3252(8) .859(3) .031(4) Uiso d . 1 . . H C11 .37064(9) .23780(7) .6934(2) .0409(3) Uani d . 1 . . C H11 .3786(9) .2074(9) .804(3) .044(5) Uiso d . 1 . . H C12 .36180(8) .21190(7) .4967(3) .0401(3) Uani d . 1 . . C H12 .3630(9) .1620(9) .475(3) .048(5) Uiso d . 1 . . H C13 .35187(7) .25563(7) .3332(2) .0359(3) Uani d . 1 . . C H13 .3452(9) .2384(8) .199(3) .038(4) Uiso d . 1 . . H C14 .35057(7) .32492(7) .3653(2) .0308(3) Uani d . 1 . . C H14 .3447(8) .3537(8) .254(3) .036(4) Uiso d . 1 . . H C15 .37452(6) .44728(6) .80705(18) .0251(2) Uani d . 1 . . C C16 .38816(7) .46420(7) .9763(2) .0332(3) Uani d . 1 . . C H16 .3986(8) .4755(8) 1.111(3) .033(4) Uiso d . 1 . . H C21 .30482(7) -.00230(7) -.2367(2) .0358(3) Uani d . 1 . . C H21 .2763(8) -.0288(8) -.329(3) .037(4) Uiso d . 1 . . H C22 .36896(8) .01618(8) -.3045(3) .0439(3) Uani d . 1 . . C H22 .3829(9) -.0001(9) -.441(3) .046(5) Uiso d . 1 . . H C23 .41138(7) .05300(8) -.1773(3) .0432(3) Uani d . 1 . . C H23 .4542(10) .0646(10) -.224(3) .056(5) Uiso d . 1 . . H O37 .09534(4) .01939(4) .06350(13) .02451(17) Uani d . 1 . . O H37 .0658(9) .0468(9) .036(3) .041(5) Uiso d . 1 . . H C24 .38938(7) .07277(7) .0143(3) .0410(3) Uani d . 1 . . C H24 .4199(10) .0993(10) .100(3) .055(5) Uiso d . 1 . . H C25 .32488(7) .05526(7) .0810(2) .0330(3) Uani d . 1 . . C H25 .3062(9) .0667(9) .215(3) .044(4) Uiso d . 1 . . H C26 .28189(6) .01699(6) -.0429(2) .0262(2) Uani d . 1 . . C C27 .21299(6) -.00289(6) .0347(2) .0250(2) Uani d . 1 . . C H27A .2042(7) -.0497(8) .007(2) .027(3) Uiso d . 1 . . H H27B .2103(7) .0006(7) .185(2) .027(4) Uiso d . 1 . . H C28 .15407(5) .04001(6) -.05373(18) .0229(2) Uani d . 1 . . C C29 .16810(5) .11519(6) -.02152(19) .0245(2) Uani d . 1 . . C C30 .18842(7) .15653(6) -.1831(2) .0312(3) Uani d . 1 . . C H30 .1922(9) .1366(9) -.319(3) .045(5) Uiso d . 1 . . H C31 .20312(8) .22435(7) -.1465(3) .0386(3) Uani d . 1 . . C H31 .2179(8) .2499(9) -.257(3) .040(4) Uiso d . 1 . . H C32 .19832(7) .25071(7) .0494(3) .0393(3) Uani d . 1 . . C H32 .2059(8) .2970(9) .077(3) .037(4) Uiso d . 1 . . H C33 .17860(7) .20979(7) .2112(2) .0366(3) Uani d . 1 . . C H33 .1740(9) .2274(9) .356(3) .042(4) Uiso d . 1 . . H C34 .16351(6) .14189(6) .1773(2) .0299(3) Uani d . 1 . . C H34 .1491(7) .1125(8) .294(2) .029(4) Uiso d . 1 . . H C35 .14079(6) .02311(6) -.27243(19) .0261(2) Uani d . 1 . . C C36 .12443(7) .00655(7) -.4409(2) .0318(3) Uani d . 1 . . C H36 .1118(9) -.0026(9) -.570(3) .045(5) Uiso d . 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 C1 .0340(7) .0312(7) .0525(9) .0060(5) .0141(6) .0047(6) C2 .0443(8) .0437(8) .0702(12) .0154(7) .0275(8) .0178(8) C3 .0329(8) .0475(9) .1004(17) .0077(7) .0215(9) .0308(10) O17 .0221(4) .0257(4) .0230(4) -.0003(3) .0020(3) .0021(3) C4 .0280(7) .0423(9) .1102(17) -.0083(6) -.0065(9) .0215(10) C5 .0291(7) .0355(7) .0668(11) -.0025(5) -.0086(7) .0067(7) C6 .0222(5) .0252(6) .0447(7) .0038(4) .0019(5) .0075(5) C7 .0236(5) .0258(5) .0296(6) .0016(4) -.0008(4) .0023(5) C8 .0214(5) .0232(5) .0207(5) -.0006(4) .0012(4) .0005(4) C9 .0198(5) .0236(5) .0264(6) -.0007(4) .0015(4) -.0015(4) C10 .0406(7) .0261(6) .0271(6) .0000(5) .0073(5) .0017(5) C11 .0539(9) .0265(6) .0422(8) -.0010(6) .0120(7) .0068(6) C12 .0408(7) .0254(6) .0541(9) -.0048(5) .0095(6) -.0056(6) C13 .0349(7) .0346(7) .0382(7) -.0019(5) -.0024(5) -.0114(6) C14 .0314(6) .0308(6) .0301(6) .0002(5) -.0044(5) -.0037(5) C15 .0256(5) .0240(5) .0257(6) -.0004(4) .0019(4) .0015(4) C16 .0415(7) .0335(6) .0245(6) -.0030(5) -.0003(5) -.0015(5) C21 .0306(6) .0382(7) .0386(7) -.0012(5) -.0003(5) -.0042(6) C22 .0372(7) .0466(8) .0479(9) -.0009(6) .0110(6) -.0019(7) C23 .0289(7) .0375(7) .0632(10) -.0042(5) .0063(7) .0010(7) O37 .0225(4) .0249(4) .0262(4) .0007(3) .0004(3) .0019(3) C24 .0302(6) .0339(7) .0588(10) -.0060(5) -.0054(6) -.0029(6) C25 .0297(6) .0298(6) .0395(7) -.0001(5) -.0036(5) -.0020(5) C26 .0236(5) .0222(5) .0327(6) .0027(4) -.0030(5) .0031(5) C27 .0236(5) .0233(5) .0280(6) .0009(4) -.0019(4) .0032(4) C28 .0222(5) .0230(5) .0234(5) -.0004(4) -.0003(4) .0008(4) C29 .0202(5) .0233(5) .0300(6) .0012(4) -.0034(4) .0010(4) C30 .0323(6) .0276(6) .0336(7) -.0014(5) -.0009(5) .0034(5) C31 .0389(7) .0280(6) .0490(8) -.0048(5) -.0035(6) .0097(6) C32 .0378(7) .0230(6) .0572(9) -.0029(5) -.0124(6) -.0001(6) C33 .0376(7) .0317(7) .0404(7) .0016(5) -.0103(6) -.0077(6) C34 .0292(6) .0277(6) .0328(7) .0010(5) -.0044(5) -.0010(5) C35 .0251(5) .0248(5) .0283(6) -.0012(4) .0002(4) .0018(4) C36 .0349(6) .0350(6) .0256(6) -.0037(5) -.0012(5) .0005(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 C1 C2 . 1.395(2) no C1 C6 . 1.398(2) no C1 H1 . 1.044(18) no C2 C3 . 1.375(3) no C2 H2 . 1.02(2) no C3 C4 . 1.377(3) no C3 H3 . 1.00(3) no O17 C8 . 1.4552(13) no O17 H17 . .83(2) no C4 C5 . 1.401(3) no C4 H4 . 1.00(3) no C5 C6 . 1.394(2) no C5 H5 . .94(2) no C6 C7 . 1.5129(17) no C7 C8 . 1.5539(16) yes C7 H7A . .975(17) no C7 H7B . .966(14) no C8 C15 . 1.4812(16) yes C8 C9 . 1.5337(16) no C9 C10 . 1.3964(17) no C9 C14 . 1.3995(18) no C10 C11 . 1.3931(19) no C10 H10 . .941(18) no C11 C12 . 1.390(2) no C11 H11 . .950(19) no C12 C13 . 1.387(2) no C12 H12 . 1.000(18) no C13 C14 . 1.3907(19) no C13 H13 . .950(18) no C14 H14 . .931(18) no C15 C16 . 1.1828(18) yes C16 H16 . .926(17) no C21 C26 . 1.394(2) no C21 C22 . 1.396(2) no C21 H21 . .977(17) no C22 C23 . 1.388(2) no C22 H22 . .98(2) no C23 C24 . 1.378(2) no C23 H23 . .93(2) no O37 C28 . 1.4516(14) no O37 H37 . .820(18) no C24 C25 . 1.395(2) no C24 H24 . .98(2) no C25 C26 . 1.3978(18) no C25 H25 . .974(19) no C26 C27 . 1.5100(16) no C27 C28 . 1.5564(16) yes C27 H27A . .961(15) no C27 H27B . .979(15) no C28 C35 . 1.4856(17) yes C28 C29 . 1.5318(16) no C29 C30 . 1.3931(18) no C29 C34 . 1.4007(18) no C30 C31 . 1.3971(19) no C30 H30 . .97(2) no C31 C32 . 1.382(2) no C31 H31 . .930(19) no C32 C33 . 1.385(2) no C32 H32 . .948(17) no C33 C34 . 1.3976(19) no C33 H33 . 1.01(2) no C34 H34 . .998(16) no C35 C36 . 1.1893(18) yes C36 H36 . .90(2) no 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' 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 C1 C6 120.67(16) no C2 C1 H1 118.0(10) no C6 C1 H1 121.3(10) no C3 C2 C1 120.43(19) no C3 C2 H2 121.3(13) no C1 C2 H2 118.3(13) no C2 C3 C4 119.59(16) no C2 C3 H3 118.3(14) no C4 C3 H3 122.0(14) no C8 O17 H17 106.5(14) no C3 C4 C5 120.76(18) no C3 C4 H4 116.9(15) no C5 C4 H4 122.4(15) no C6 C5 C4 120.13(19) no C6 C5 H5 119.8(13) no C4 C5 H5 119.9(13) no C5 C6 C1 118.40(13) no C5 C6 C7 120.93(14) no C1 C6 C7 120.66(12) no C6 C7 C8 114.50(10) yes C6 C7 H7A 108.5(10) no C8 C7 H7A 106.5(10) no C6 C7 H7B 108.8(8) no C8 C7 H7B 107.1(8) no H7A C7 H7B 111.4(12) no O17 C8 C15 108.16(9) yes O17 C8 C9 109.55(9) no C15 C8 C9 111.75(9) no O17 C8 C7 104.42(9) no C15 C8 C7 110.21(9) no C9 C8 C7 112.41(9) no C10 C9 C14 118.67(11) no C10 C9 C8 122.07(11) no C14 C9 C8 119.22(10) no C11 C10 C9 120.52(13) no C11 C10 H10 121.0(9) no C9 C10 H10 118.5(9) no C12 C11 C10 120.31(14) no C12 C11 H11 118.7(11) no C10 C11 H11 120.9(11) no C13 C12 C11 119.53(12) no C13 C12 H12 120.9(11) no C11 C12 H12 119.5(11) no C12 C13 C14 120.38(13) no C12 C13 H13 120.1(10) no C14 C13 H13 119.5(10) no C13 C14 C9 120.58(13) no C13 C14 H14 119.4(11) no C9 C14 H14 120.0(11) no C16 C15 C8 177.64(13) yes C15 C16 H16 177.4(10) no C26 C21 C22 120.74(13) no C26 C21 H21 120.9(10) no C22 C21 H21 118.4(10) no C23 C22 C21 120.17(15) no C23 C22 H22 122.6(10) no C21 C22 H22 117.1(10) no C24 C23 C22 119.81(14) no C24 C23 H23 120.8(13) no C22 C23 H23 119.4(13) no C28 O37 H37 105.7(12) no C23 C24 C25 120.06(14) no C23 C24 H24 118.2(12) no C25 C24 H24 121.7(12) no C24 C25 C26 121.03(14) no C24 C25 H25 124.6(11) no C26 C25 H25 114.3(11) no C21 C26 C25 118.15(12) no C21 C26 C27 121.76(11) no C25 C26 C27 120.09(12) no C26 C27 C28 114.42(9) yes C26 C27 H27A 110.8(9) no C28 C27 H27A 108.8(9) no C26 C27 H27B 111.4(8) no C28 C27 H27B 106.8(9) no H27A C27 H27B 104.1(13) no O37 C28 C35 107.30(9) yes O37 C28 C29 110.39(9) no C35 C28 C29 112.52(10) no O37 C28 C27 104.74(9) no C35 C28 C27 111.35(10) no C29 C28 C27 110.21(9) no C30 C29 C34 119.55(11) no C30 C29 C28 121.51(11) no C34 C29 C28 118.86(10) no C29 C30 C31 119.93(13) no C29 C30 H30 118.1(11) no C31 C30 H30 122.0(11) no C32 C31 C30 120.48(14) no C32 C31 H31 122.1(11) no C30 C31 H31 117.4(11) no C31 C32 C33 119.92(12) no C31 C32 H32 122.1(10) no C33 C32 H32 117.9(10) no C32 C33 C34 120.36(14) no C32 C33 H33 122.1(10) no C34 C33 H33 117.5(10) no C33 C34 C29 119.76(13) no C33 C34 H34 120.4(9) no C29 C34 H34 119.9(9) no C36 C35 C28 173.46(13) yes C35 C36 H36 175.6(12) 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 C16 H16 O17 1_556 .93(2) 2.31(2) 3.181(2) 156.0(10) yes C36 H36 O37 1_554 .90(2) 2.44(2) 3.2862(16) 156(2) yes O37 H37 O37 4_555 .82(2) 2.05(2) 2.8520(10) 166(2) yes O17 H17 O17 4_656 .83(2) 2.00(2) 2.8200(12) 169(2) yes _cod_database_fobs_code 2011509