#------------------------------------------------------------------------------ #$Date: 2016-02-21 00:03:34 +0000 (Sun, 21 Feb 2016) $ #$Revision: 176798 $ #$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238982.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2238982 loop_ _publ_author_name 'Souza, Bruno S.' 'Bortoluzzi, Adailton J.' 'Nome, Faruk' _publ_section_title ; 1-Carboxynaphthalen-2-yl acetate monohydrate ; _journal_coeditor_code HG5366 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o105 _journal_paper_doi 10.1107/S1600536813034338 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C13 H10 O4, H2 O' _chemical_formula_moiety 'C13 H10 O4, H2 O' _chemical_formula_sum 'C13 H12 O5' _chemical_formula_weight 248.23 _chemical_name_systematic ; 1-Carboxynaphthalen-2-yl acetate monohydrate ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2013 _cell_angle_alpha 90 _cell_angle_beta 94.863(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.0539(4) _cell_length_b 11.6668(6) _cell_length_c 11.8297(19) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 15.54 _cell_measurement_theta_min 6.85 _cell_volume 1245.1(2) _computing_cell_refinement ; SET4 in CAD-4 Software (Enraf--Nonius, 1989) ; _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'HELENA (Spek, 1996)' _computing_molecular_graphics ; PLATON (Spek, 2009) ; _computing_publication_material 'SHELXL2013 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL2013 (Sheldrick, 2008)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2405 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.464 _diffrn_reflns_theta_min 2.456 _diffrn_standards_decay_% 1 _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.324 _exptl_crystal_description 'irregular block' _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.26 _refine_diff_density_max 0.152 _refine_diff_density_min -0.117 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 2294 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.1122 _refine_ls_R_factor_gt 0.0449 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.2858P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1041 _refine_ls_wR_factor_ref 0.1248 _reflns_number_gt 1298 _reflns_number_total 2294 _reflns_threshold_expression I>2\s(I) _cod_data_source_file hg5366sup1.cif _cod_data_source_block I _cod_database_code 2238982 _cod_database_fobs_code 2238982 #BEGIN Tags that were not found in dictionaries: _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; TITL 1-carboxy-2-naphthyl acetate - P 21/n CELL 0.71073 9.0539 11.6668 11.8297 90.000 94.863 90.000 ZERR 4.00 0.0004 0.0006 0.0019 0.000 0.010 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H O UNIT 52 48 20 MERG 2 EQIV $1 X+1, Y, Z EQIV $2 -X+1, -Y, -Z+1 HTAB O3 O1W HTAB O1W O2_$1 HTAB O1W O4_$2 FMAP 2 PLAN 5 BOND $H CONF ACTA L.S. 6 TEMP 20.00 WGHT 0.041900 0.285800 FVAR 0.98498 C1 1 0.092313 0.203622 0.239335 11.00000 0.05746 0.06776 = 0.05367 -0.00351 0.00617 -0.00801 C2 1 0.190647 0.128720 0.199708 11.00000 0.04871 0.06020 = 0.05279 0.00284 0.00426 -0.00706 C3 1 0.184856 0.106293 0.080567 11.00000 0.05351 0.05902 = 0.05299 0.00280 0.00530 -0.00495 C4 1 0.280155 0.028313 0.031525 11.00000 0.06881 0.07462 = 0.06462 0.00045 0.00895 0.00840 AFIX 43 H4 2 0.352046 -0.010535 0.077504 11.00000 -1.20000 AFIX 0 C5 1 0.267727 0.009438 -0.082704 11.00000 0.09774 0.08438 = 0.06679 -0.00646 0.01933 0.00658 AFIX 43 H5 2 0.331890 -0.041815 -0.113630 11.00000 -1.20000 AFIX 0 C6 1 0.160794 0.065516 -0.153628 11.00000 0.11152 0.09570 = 0.05147 -0.00512 0.01012 -0.00132 AFIX 43 H6 2 0.153910 0.051766 -0.231334 11.00000 -1.20000 AFIX 0 C7 1 0.067284 0.139679 -0.109804 11.00000 0.09064 0.09137 = 0.05537 0.00936 -0.00527 -0.00247 AFIX 43 H7 2 -0.004285 0.176503 -0.157838 11.00000 -1.20000 AFIX 0 C8 1 0.075706 0.162741 0.007945 11.00000 0.06320 0.06534 = 0.05832 0.00859 0.00415 -0.00133 C9 1 -0.020982 0.241037 0.055286 11.00000 0.07209 0.08089 = 0.07267 0.01159 -0.00048 0.01396 AFIX 43 H9 2 -0.091496 0.279391 0.007607 11.00000 -1.20000 AFIX 0 C10 1 -0.013584 0.261695 0.168518 11.00000 0.06759 0.07480 = 0.07546 -0.00237 0.00788 0.01177 AFIX 43 H10 2 -0.077918 0.313594 0.198309 11.00000 -1.20000 AFIX 0 C11 1 0.002061 0.179139 0.417595 11.00000 0.06191 0.08497 = 0.06275 -0.00935 0.01520 -0.00179 C12 1 0.028097 0.202850 0.540408 11.00000 0.09998 0.10623 = 0.06349 -0.01474 0.01713 -0.00076 AFIX 123 H12A 2 0.114313 0.250383 0.554079 10.50000 -1.50000 H12B 2 0.043334 0.131943 0.580897 10.50000 -1.50000 H12C 2 -0.056446 0.241625 0.566013 10.50000 -1.50000 H12D 2 -0.046845 0.165584 0.579914 10.50000 -1.50000 H12E 2 0.024134 0.284024 0.553095 10.50000 -1.50000 H12F 2 0.123913 0.174343 0.567980 10.50000 -1.50000 AFIX 0 C13 1 0.301811 0.072457 0.282189 11.00000 0.05540 0.07760 = 0.05270 0.00230 0.00648 0.00081 O1 3 0.103695 0.228719 0.356299 11.00000 0.06724 0.08189 = 0.06033 -0.01376 0.01240 -0.01111 O2 3 -0.095736 0.122597 0.373304 11.00000 0.08532 0.16222 = 0.08056 -0.02529 0.02158 -0.05445 O1W 3 0.644156 0.024531 0.413648 11.00000 0.06113 0.10754 = 0.07731 0.01558 -0.00260 -0.01478 O3 3 0.438816 0.091874 0.263115 11.00000 0.05391 0.11880 = 0.07162 0.01528 -0.00007 -0.00073 O4 3 0.266791 0.018197 0.361956 11.00000 0.07976 0.15348 = 0.08463 0.05435 0.00709 -0.00014 H1WA 2 0.726580 0.067726 0.407303 11.00000 0.11761 H1WB 2 0.646979 0.012021 0.486095 11.00000 0.12712 H3 2 0.503874 0.062518 0.325182 11.00000 0.14140 HKLF 4 REM 1-carboxy-2-naphthyl acetate - P 21/n REM R1 = 0.0449 for 1298 Fo > 4sig(Fo) and 0.1122 for all 2294 data REM 175 parameters refined using 0 restraints END WGHT 0.0419 0.2860 REM Highest difference peak 0.152, deepest hole -0.117, 1-sigma level 0.031 Q1 1 0.2678 -0.0256 0.2953 11.00000 0.05 0.15 Q2 1 0.3017 -0.0395 0.1924 11.00000 0.05 0.12 Q3 1 0.0806 0.1090 0.0563 11.00000 0.05 0.12 Q4 1 0.0033 0.1871 0.2020 11.00000 0.05 0.12 Q5 1 0.1412 0.2158 0.5665 11.00000 0.05 0.12 ; _shelxl_version_number 2013 #END Tags that were not found in dictionaries loop_ _space_group_symop_operation_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_type_symbol _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_occupancy C C1 0.0923(3) 0.2036(2) 0.23934(19) 0.0595(6) Uani d 1 C C2 0.1906(2) 0.12872(19) 0.19971(18) 0.0539(6) Uani d 1 C C3 0.1849(2) 0.1063(2) 0.08057(18) 0.0551(6) Uani d 1 C C4 0.2802(3) 0.0283(2) 0.0315(2) 0.0692(7) Uani d 1 H H4 0.3520 -0.0105 0.0775 0.083 Uiso calc 1 C C5 0.2677(3) 0.0094(3) -0.0827(2) 0.0823(8) Uani d 1 H H5 0.3319 -0.0418 -0.1136 0.099 Uiso calc 1 C C6 0.1608(4) 0.0655(3) -0.1536(2) 0.0860(9) Uani d 1 H H6 0.1539 0.0518 -0.2313 0.103 Uiso calc 1 C C7 0.0673(3) 0.1397(3) -0.1098(2) 0.0798(8) Uani d 1 H H7 -0.0043 0.1765 -0.1578 0.096 Uiso calc 1 C C8 0.0757(3) 0.1627(2) 0.0079(2) 0.0623(7) Uani d 1 C C9 -0.0210(3) 0.2410(2) 0.0553(2) 0.0756(8) Uani d 1 H H9 -0.0915 0.2794 0.0076 0.091 Uiso calc 1 C C10 -0.0136(3) 0.2617(2) 0.1685(2) 0.0725(8) Uani d 1 H H10 -0.0779 0.3136 0.1983 0.087 Uiso calc 1 C C11 0.0021(3) 0.1791(2) 0.4176(2) 0.0693(7) Uani d 1 C C12 0.0281(3) 0.2029(3) 0.5404(2) 0.0893(9) Uani d 1 H H12A 0.1143 0.2504 0.5541 0.134 Uiso calc 0.5 H H12B 0.0433 0.1319 0.5809 0.134 Uiso calc 0.5 H H12C -0.0564 0.2416 0.5660 0.134 Uiso calc 0.5 H H12D -0.0468 0.1656 0.5799 0.134 Uiso calc 0.5 H H12E 0.0241 0.2840 0.5531 0.134 Uiso calc 0.5 H H12F 0.1239 0.1743 0.5680 0.134 Uiso calc 0.5 C C13 0.3018(3) 0.0725(2) 0.2822(2) 0.0618(7) Uani d 1 O O1 0.10370(18) 0.22872(15) 0.35630(13) 0.0694(5) Uani d 1 O O2 -0.0957(2) 0.1226(2) 0.37330(17) 0.1085(8) Uani d 1 O O1W 0.6442(2) 0.0245(2) 0.4136(2) 0.0825(6) Uani d 1 O O3 0.4388(2) 0.09187(19) 0.26311(16) 0.0817(6) Uani d 1 O O4 0.2668(2) 0.0182(2) 0.36196(17) 0.1059(8) Uani d 1 H H1WA 0.727(4) 0.068(3) 0.407(3) 0.118(12) Uiso d 1 H H1WB 0.647(4) 0.012(3) 0.486(3) 0.127(14) Uiso d 1 H H3 0.504(4) 0.063(3) 0.325(3) 0.141(14) Uiso d 1 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 0.0575(15) 0.0678(17) 0.0537(14) -0.0080(13) 0.0062(12) -0.0035(12) C2 0.0487(13) 0.0602(15) 0.0528(14) -0.0071(12) 0.0043(11) 0.0028(11) C3 0.0535(14) 0.0590(15) 0.0530(14) -0.0050(12) 0.0053(11) 0.0028(11) C4 0.0688(17) 0.0746(18) 0.0646(17) 0.0084(14) 0.0089(13) 0.0004(13) C5 0.098(2) 0.084(2) 0.0668(19) 0.0066(17) 0.0193(16) -0.0065(16) C6 0.112(3) 0.096(2) 0.0515(16) -0.001(2) 0.0101(17) -0.0051(16) C7 0.091(2) 0.091(2) 0.0554(16) -0.0025(17) -0.0053(14) 0.0094(15) C8 0.0632(16) 0.0653(17) 0.0583(15) -0.0013(13) 0.0042(12) 0.0086(12) C9 0.0721(18) 0.081(2) 0.0727(18) 0.0140(15) -0.0005(14) 0.0116(15) C10 0.0676(18) 0.0748(19) 0.0755(19) 0.0118(14) 0.0079(14) -0.0024(14) C11 0.0619(16) 0.085(2) 0.0627(16) -0.0018(15) 0.0152(14) -0.0094(14) C12 0.100(2) 0.106(2) 0.0635(17) -0.0008(19) 0.0171(16) -0.0147(16) C13 0.0554(16) 0.0776(18) 0.0527(14) 0.0008(13) 0.0065(11) 0.0023(13) O1 0.0672(11) 0.0819(12) 0.0603(11) -0.0111(9) 0.0124(9) -0.0138(9) O2 0.0853(14) 0.162(2) 0.0806(14) -0.0544(15) 0.0216(11) -0.0253(14) O1W 0.0611(13) 0.1075(16) 0.0773(14) -0.0148(12) -0.0026(10) 0.0156(12) O3 0.0539(11) 0.1188(17) 0.0716(12) -0.0007(11) -0.0001(9) 0.0153(11) O4 0.0798(14) 0.153(2) 0.0846(15) -0.0001(14) 0.0071(11) 0.0543(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C2 C1 C10 122.9(2) C2 C1 O1 118.5(2) C10 C1 O1 118.6(2) C1 C2 C3 119.2(2) C1 C2 C13 118.8(2) C3 C2 C13 122.0(2) C4 C3 C8 118.0(2) C4 C3 C2 123.4(2) C8 C3 C2 118.6(2) C5 C4 C3 120.6(3) C5 C4 H4 119.7 C3 C4 H4 119.7 C4 C5 C6 121.1(3) C4 C5 H5 119.4 C6 C5 H5 119.4 C7 C6 C5 119.9(3) C7 C6 H6 120.0 C5 C6 H6 120.0 C6 C7 C8 121.3(3) C6 C7 H7 119.4 C8 C7 H7 119.4 C9 C8 C7 122.0(2) C9 C8 C3 119.0(2) C7 C8 C3 119.1(2) C10 C9 C8 121.7(2) C10 C9 H9 119.1 C8 C9 H9 119.1 C9 C10 C1 118.7(2) C9 C10 H10 120.6 C1 C10 H10 120.6 O2 C11 O1 121.1(2) O2 C11 C12 126.0(3) O1 C11 C12 112.9(2) C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C11 C12 H12D 109.5 H12A C12 H12D 141.1 H12B C12 H12D 56.3 H12C C12 H12D 56.3 C11 C12 H12E 109.5 H12A C12 H12E 56.3 H12B C12 H12E 141.1 H12C C12 H12E 56.3 H12D C12 H12E 109.5 C11 C12 H12F 109.5 H12A C12 H12F 56.3 H12B C12 H12F 56.3 H12C C12 H12F 141.1 H12D C12 H12F 109.5 H12E C12 H12F 109.5 O4 C13 O3 123.2(2) O4 C13 C2 122.5(2) O3 C13 C2 114.2(2) C11 O1 C1 116.24(19) H1WA O1W H1WB 103(3) C13 O3 H3 110(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.359(3) C1 C10 1.394(3) C1 O1 1.409(3) C2 C3 1.430(3) C2 C13 1.493(3) C3 C4 1.412(3) C3 C8 1.416(3) C4 C5 1.364(4) C4 H4 0.9300 C5 C6 1.390(4) C5 H5 0.9300 C6 C7 1.345(4) C6 H6 0.9300 C7 C8 1.414(3) C7 H7 0.9300 C8 C9 1.413(4) C9 C10 1.357(4) C9 H9 0.9300 C10 H10 0.9300 C11 O2 1.190(3) C11 O1 1.349(3) C11 C12 1.478(3) C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 C12 H12D 0.9600 C12 H12E 0.9600 C12 H12F 0.9600 C13 O4 1.201(3) C13 O3 1.299(3) O1W H1WA 0.91(4) O1W H1WB 0.87(4) O3 H3 0.96(4) 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 O3 H3 O1W . 0.96(4) 1.64(4) 2.585(3) 167(3) y O1W H1WA O2 1_655 0.91(4) 1.81(4) 2.697(3) 165(3) y O1W H1WB O4 3_656 0.87(4) 1.93(4) 2.754(3) 158(3) y 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 C10 C1 C2 C3 -1.1(3) O1 C1 C2 C3 -177.20(19) C10 C1 C2 C13 178.8(2) O1 C1 C2 C13 2.7(3) C1 C2 C3 C4 -178.7(2) C13 C2 C3 C4 1.4(3) C1 C2 C3 C8 -0.4(3) C13 C2 C3 C8 179.7(2) C8 C3 C4 C5 0.7(4) C2 C3 C4 C5 179.1(2) C3 C4 C5 C6 -0.5(4) C4 C5 C6 C7 -0.1(5) C5 C6 C7 C8 0.4(5) C6 C7 C8 C9 179.5(3) C6 C7 C8 C3 -0.1(4) C4 C3 C8 C9 179.9(2) C2 C3 C8 C9 1.5(3) C4 C3 C8 C7 -0.5(3) C2 C3 C8 C7 -178.9(2) C7 C8 C9 C10 179.1(3) C3 C8 C9 C10 -1.3(4) C8 C9 C10 C1 -0.1(4) C2 C1 C10 C9 1.3(4) O1 C1 C10 C9 177.5(2) C1 C2 C13 O4 55.8(4) C3 C2 C13 O4 -124.3(3) C1 C2 C13 O3 -121.1(2) C3 C2 C13 O3 58.8(3) O2 C11 O1 C1 -3.9(4) C12 C11 O1 C1 175.8(2) C2 C1 O1 C11 -104.4(3) C10 C1 O1 C11 79.3(3)