#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200444.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_2200444 loop_ _publ_author_name 'Srinivasan, N.' 'Sridhar, B.' 'Rajaram, R. K.' _publ_section_title ; Bis(DL-phenylalaninium) sulfate monohydrate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o772 _journal_page_last o774 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac '2C9 H12 N O2 1+, O4 S 2-, H2 O' _chemical_formula_moiety '2C9 H12 N O2 1+, O4 S 2-, H2 O' _chemical_formula_sum 'C18 H26 N2 O9 S' _chemical_formula_weight 446.47 _chemical_name_common 'Bis(DL-phenylalaninium)sulfate monohydrate' _chemical_name_systematic ; ? ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.70(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.560(2) _cell_length_b 6.6000(12) _cell_length_c 22.115(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15.80 _cell_measurement_theta_min 7.98 _cell_volume 2125.0(6) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD-4 Software' _computing_molecular_graphics 'PLATON (Spek, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .984 _diffrn_measured_fraction_theta_max .984 _diffrn_measurement_device_type 'Enraf-Nonius sealed tube' _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 .021 _diffrn_reflns_av_sigmaI/netI .027 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 3825 _diffrn_reflns_theta_full 24.98 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 2.80 _diffrn_standards_decay_% none _diffrn_standards_interval_count 3 _diffrn_standards_interval_time 60 _diffrn_standards_number 25 _exptl_absorpt_coefficient_mu .205 _exptl_absorpt_correction_T_max .980 _exptl_absorpt_correction_T_min .951 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_meas 1.39 _exptl_crystal_density_method 'flotation in a mixture of bromoform and xylene' _exptl_crystal_description needles _exptl_crystal_F_000 944 _exptl_crystal_size_max .4 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 _refine_diff_density_max .52 _refine_diff_density_min -.26 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 3671 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all .066 _refine_ls_R_factor_gt .046 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0530P)^2^+1.5922P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .119 _reflns_number_gt 2806 _reflns_number_total 3671 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6038.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 2124.9(6) _cod_database_code 2200444 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_type_symbol S .27906(4) .20427(9) -.10666(3) .02978(17) Uani d . 1 S O1 .32429(11) .2919(3) -.05195(7) .0369(4) Uani d . 1 O O2 .19967(12) .0864(3) -.08762(9) .0530(6) Uani d . 1 O O3 .34514(12) .0639(3) -.13478(8) .0468(5) Uani d . 1 O O4 .25546(17) .3665(3) -.14796(10) .0673(7) Uani d . 1 O OW .57935(17) .4282(4) .18734(12) .0684(7) Uani d D 1 O H1 .628(2) .513(6) .1784(18) .101(14) Uiso d D 1 H H2 .539(2) .445(6) .1566(13) .081(12) Uiso d D 1 H O1A .50678(12) .3299(3) .04872(8) .0447(5) Uani d . 1 O O1B .49823(11) .1962(3) -.04434(8) .0433(5) Uani d . 1 O H1B .4439 .2278 -.0425 .065 Uiso calc R 1 H C11 .54087(16) .2536(3) .00510(11) .0318(5) Uani d . 1 C C12 .64337(15) .2134(4) .00081(10) .0317(5) Uani d . 1 C H12 .6529 .0672 -.0037 .038 Uiso calc R 1 H N11 .68793(14) .2804(3) .05773(9) .0344(5) Uani d . 1 N H11A .7481 .2577 .0559 .052 Uiso calc R 1 H H11B .6647 .2116 .0886 .052 Uiso calc R 1 H H11C .6779 .4122 .0630 .052 Uiso calc R 1 H C13 .68506(17) .3202(4) -.05313(12) .0404(6) Uani d . 1 C H13A .6562 .2692 -.0898 .048 Uiso calc R 1 H H13B .6715 .4638 -.0505 .048 Uiso calc R 1 H C14 .78803(17) .2929(4) -.05764(11) .0380(6) Uani d . 1 C C15 .8272(2) .1050(5) -.06414(16) .0612(9) Uani d . 1 C H15 .7900 -.0095 -.0660 .073 Uiso calc R 1 H C16 .9219(2) .0849(6) -.06797(17) .0706(10) Uani d . 1 C H16 .9478 -.0431 -.0719 .085 Uiso calc R 1 H C17 .9768(2) .2511(6) -.06595(14) .0621(10) Uani d . 1 C H17 1.0402 .2369 -.0686 .075 Uiso calc R 1 H C18 .9391(2) .4382(6) -.06004(13) .0557(9) Uani d . 1 C H18 .9767 .5521 -.0593 .067 Uiso calc R 1 H C19 .84491(19) .4598(5) -.05507(12) .0451(7) Uani d . 1 C H19 .8198 .5881 -.0500 .054 Uiso calc R 1 H O2A -.19852(14) .2220(3) .20968(9) .0572(6) Uani d . 1 O O2B -.10045(13) .1978(4) .13422(10) .0584(6) Uani d . 1 O H2B -.1328 .1015 .1242 .088 Uiso calc R 1 H C21 -.13276(16) .2795(4) .18392(11) .0352(6) Uani d . 1 C C22 -.07529(15) .4580(4) .20500(11) .0323(5) Uani d . 1 C H22 -.0597 .5423 .1701 .039 Uiso calc R 1 H N21 -.13195(13) .5768(3) .24707(9) .0334(5) Uani d . 1 N H21A -.1001 .6834 .2603 .050 Uiso calc R 1 H H21B -.1474 .4995 .2783 .050 Uiso calc R 1 H H21C -.1826 .6192 .2280 .050 Uiso calc R 1 H C23 .01357(16) .3814(4) .23563(14) .0441(7) Uani d . 1 C H23A -.0024 .2894 .2680 .053 Uiso calc R 1 H H23B .0487 .3056 .2063 .053 Uiso calc R 1 H C24 .07292(15) .5482(4) .26114(12) .0366(6) Uani d . 1 C C25 .11920(18) .6813(5) .22420(12) .0465(7) Uani d . 1 C H25 .1133 .6686 .1824 .056 Uiso calc R 1 H C26 .1739(2) .8323(5) .24803(14) .0577(8) Uani d . 1 C H26 .2040 .9218 .2225 .069 Uiso calc R 1 H C27 .1840(2) .8505(6) .31019(15) .0611(9) Uani d . 1 C H27 .2219 .9502 .3266 .073 Uiso calc R 1 H C28 .1380(2) .7217(5) .34712(13) .0555(8) Uani d . 1 C H28 .1438 .7355 .3888 .067 Uiso calc R 1 H C29 .08293(18) .5708(5) .32339(13) .0463(7) Uani d . 1 C H29 .0522 .4834 .3492 .056 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 S .0282(3) .0276(3) .0333(3) -.0037(3) -.0074(2) -.0020(3) O1 .0336(9) .0384(10) .0387(10) -.0027(8) -.0090(7) -.0088(8) O2 .0362(10) .0633(14) .0597(13) -.0206(10) .0064(9) -.0188(11) O3 .0380(10) .0588(13) .0439(11) .0020(9) .0019(8) -.0149(9) O4 .0854(16) .0513(13) .0644(14) .0018(12) -.0350(12) .0122(11) OW .0604(15) .0556(15) .0889(19) -.0116(12) -.0160(13) .0189(13) O1A .0376(10) .0548(12) .0418(11) .0040(9) .0065(8) .0005(9) O1B .0291(9) .0482(11) .0523(11) .0011(9) -.0069(8) -.0123(9) C11 .0314(12) .0225(12) .0415(14) -.0014(10) .0002(11) .0022(11) C12 .0298(12) .0311(12) .0340(12) -.0016(11) -.0032(9) -.0026(10) N11 .0346(11) .0331(11) .0353(11) -.0014(9) -.0041(9) -.0002(9) C13 .0345(13) .0487(17) .0379(14) .0009(12) .0001(11) .0058(12) C14 .0337(13) .0482(16) .0322(13) .0026(13) .0024(10) .0021(12) C15 .0512(18) .0501(19) .083(2) -.0004(16) .0156(16) .0005(17) C16 .054(2) .068(2) .090(3) .0240(19) .0210(18) .014(2) C17 .0317(15) .104(3) .0508(18) .0092(18) .0026(13) .0097(19) C18 .0393(16) .085(3) .0431(17) -.0165(16) -.0020(12) -.0015(16) C19 .0449(15) .0493(17) .0412(15) -.0031(13) .0005(12) -.0034(13) O2A .0453(11) .0670(14) .0597(12) -.0273(11) .0167(10) -.0143(11) O2B .0465(12) .0628(14) .0664(14) -.0218(10) .0188(10) -.0313(11) C21 .0258(12) .0417(14) .0381(13) -.0018(11) -.0002(10) -.0030(12) C22 .0242(11) .0385(14) .0342(13) -.0021(10) .0015(9) -.0029(11) N21 .0280(10) .0395(12) .0325(11) .0024(9) -.0003(8) -.0006(9) C23 .0266(13) .0415(15) .0641(18) .0007(11) -.0047(12) -.0060(14) C24 .0205(11) .0451(15) .0441(15) .0028(11) -.0005(10) -.0046(12) C25 .0371(14) .066(2) .0359(14) -.0110(14) .0009(11) -.0085(14) C26 .0496(17) .068(2) .0553(19) -.0253(16) .0070(14) -.0048(16) C27 .0469(17) .075(2) .061(2) -.0210(17) .0007(15) -.0251(18) C28 .0464(16) .080(2) .0401(15) -.0041(16) -.0038(13) -.0153(16) C29 .0351(14) .0601(19) .0436(15) -.0010(13) .0005(11) .0047(14) 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' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 '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 O4 S O2 113.20(14) O4 S O3 110.44(14) O2 S O3 108.01(12) O4 S O1 108.98(12) O2 S O1 108.47(11) O3 S O1 107.57(10) H1 OW H2 105(4) C11 O1B H1B 109.5 O1A C11 O1B 126.7(2) O1A C11 C12 122.6(2) O1B C11 C12 110.7(2) N11 C12 C13 110.8(2) N11 C12 C11 108.42(19) C13 C12 C11 111.7(2) N11 C12 H12 108.6 C13 C12 H12 108.6 C11 C12 H12 108.6 C12 N11 H11A 109.5 C12 N11 H11B 109.5 H11A N11 H11B 109.5 C12 N11 H11C 109.5 H11A N11 H11C 109.5 H11B N11 H11C 109.5 C14 C13 C12 113.7(2) C14 C13 H13A 108.8 C12 C13 H13A 108.8 C14 C13 H13B 108.8 C12 C13 H13B 108.8 H13A C13 H13B 107.7 C15 C14 C19 118.4(2) C15 C14 C13 121.8(3) C19 C14 C13 119.8(3) C14 C15 C16 120.4(3) C14 C15 H15 119.8 C16 C15 H15 119.8 C17 C16 C15 120.4(3) C17 C16 H16 119.8 C15 C16 H16 119.8 C18 C17 C16 119.9(3) C18 C17 H17 120.0 C16 C17 H17 120.0 C17 C18 C19 120.2(3) C17 C18 H18 119.9 C19 C18 H18 119.9 C14 C19 C18 120.6(3) C14 C19 H19 119.7 C18 C19 H19 119.7 C21 O2B H2B 109.5 O2A C21 O2B 124.8(2) O2A C21 C22 123.3(2) O2B C21 C22 111.9(2) N21 C22 C21 107.22(19) N21 C22 C23 111.7(2) C21 C22 C23 109.8(2) N21 C22 H22 109.4 C21 C22 H22 109.4 C23 C22 H22 109.4 C22 N21 H21A 109.5 C22 N21 H21B 109.5 H21A N21 H21B 109.5 C22 N21 H21C 109.5 H21A N21 H21C 109.5 H21B N21 H21C 109.5 C24 C23 C22 113.6(2) C24 C23 H23A 108.8 C22 C23 H23A 108.8 C24 C23 H23B 108.8 C22 C23 H23B 108.8 H23A C23 H23B 107.7 C25 C24 C29 118.2(2) C25 C24 C23 121.7(2) C29 C24 C23 120.1(3) C26 C25 C24 121.2(3) C26 C25 H25 119.4 C24 C25 H25 119.4 C25 C26 C27 119.7(3) C25 C26 H26 120.1 C27 C26 H26 120.1 C28 C27 C26 119.6(3) C28 C27 H27 120.2 C26 C27 H27 120.2 C27 C28 C29 120.8(3) C27 C28 H28 119.6 C29 C28 H28 119.6 C28 C29 C24 120.5(3) C28 C29 H29 119.7 C24 C29 H29 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S O4 1.446(2) ? S O2 1.4597(19) ? S O3 1.4782(19) ? S O1 1.4876(17) ? OW H1 .92(2) ? OW H2 .90(2) ? O1A C11 1.201(3) yes O1B C11 1.307(3) yes O1B H1B .82 ? C11 C12 1.520(3) ? C12 N11 1.477(3) ? C12 C13 1.519(3) ? C12 H12 .98 ? N11 H11A .89 ? N11 H11B .89 ? N11 H11C .89 ? C13 C14 1.515(3) ? C13 H13A .97 ? C13 H13B .97 ? C14 C15 1.373(4) ? C14 C19 1.379(4) ? C15 C16 1.389(4) ? C15 H15 .93 ? C16 C17 1.358(5) ? C16 H16 .93 ? C17 C18 1.358(5) ? C17 H17 .93 ? C18 C19 1.385(4) ? C18 H18 .93 ? C19 H19 .93 ? O2A C21 1.183(3) yes O2B C21 1.316(3) yes O2B H2B .82 ? C21 C22 1.516(3) ? C22 N21 1.476(3) ? C22 C23 1.538(3) ? C22 H22 .98 ? N21 H21A .89 ? N21 H21B .89 ? N21 H21C .89 ? C23 C24 1.505(4) ? C23 H23A .97 ? C23 H23B .97 ? C24 C25 1.381(4) ? C24 C29 1.391(4) ? C25 C26 1.377(4) ? C25 H25 .93 ? C26 C27 1.386(4) ? C26 H26 .93 ? C27 C28 1.361(5) ? C27 H27 .93 ? C28 C29 1.378(4) ? C28 H28 .93 ? C29 H29 .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 O1B H1B O1 . .82 1.80 2.614(2) 170 O2B H2B O2 3_555 .82 1.77 2.575(3) 168 N11 H11A O2 3_655 .89 2.49 2.992(3) 116 N11 H11B O3 3_655 .89 2.09 2.884(3) 148 N11 H11C O1 3_665 .89 1.97 2.831(3) 163 N11 H11C O4 3_665 .89 2.56 3.170(3) 126 N21 H21A OW 2_555 .89 2.01 2.836(3) 154 N21 H21C O4 3_565 .89 2.05 2.843(3) 147 N21 H21C O2A 2_455 .89 2.33 2.826(3) 115 N21 H21B O3 4_566 .89 1.97 2.797(3) 154 OW H1 O4 3_665 .92(2) 2.00(2) 2.904(3) 165(4) OW H2 O1A . .90(2) 2.54(3) 3.295(3) 142(3) 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 O1A C11 C12 N11 .8(3) yes O1B C11 C12 N11 -179.8(2) ? O1A C11 C12 C13 -121.6(3) ? O1B C11 C12 C13 57.8(3) ? N11 C12 C13 C14 56.2(3) yes C11 C12 C13 C14 177.2(2) yes C12 C13 C14 C15 60.9(4) yes C12 C13 C14 C19 -119.0(3) ? C19 C14 C15 C16 .1(5) ? C13 C14 C15 C16 -179.8(3) ? C14 C15 C16 C17 -.7(6) ? C15 C16 C17 C18 .1(5) ? C16 C17 C18 C19 1.0(5) ? C15 C14 C19 C18 1.1(4) ? C13 C14 C19 C18 -179.0(2) ? C17 C18 C19 C14 -1.7(4) ? O2A C21 C22 N21 -18.5(4) yes O2B C21 C22 N21 161.7(2) ? O2A C21 C22 C23 103.1(3) ? O2B C21 C22 C23 -76.7(3) ? N21 C22 C23 C24 -58.1(3) yes C21 C22 C23 C24 -176.9(2) yes C22 C23 C24 C25 -70.0(3) yes C22 C23 C24 C29 110.5(3) ? C29 C24 C25 C26 .1(4) ? C23 C24 C25 C26 -179.5(3) ? C24 C25 C26 C27 .8(5) ? C25 C26 C27 C28 -1.5(5) ? C26 C27 C28 C29 1.2(5) ? C27 C28 C29 C24 -.4(5) ? C25 C24 C29 C28 -.3(4) ? C23 C24 C29 C28 179.2(3) ?