#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013206.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_2013206 loop_ _publ_author_name 'Zabadal, Miroslav' 'Heger, Dominik' 'Ne\N-(1-Naphthylacetyl)glycine phenacyl ester and phenacyl (1-naphthylacetoxy)acetate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o77 _journal_page_last o79 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C22 H18 O5' _chemical_formula_moiety 'C22 H18 O5' _chemical_formula_sum 'C22 H18 O5' _chemical_formula_weight 362.36 _chemical_name_common ; Phenacyl (1-naphthylacetoxy)acetate ; _chemical_name_systematic ; ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 102.50(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.927(2) _cell_length_b 11.413(2) _cell_length_c 17.875(4) _cell_measurement_reflns_used 500 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.84 _cell_measurement_theta_min 4.54 _cell_volume 1778.0(7) _computing_cell_refinement Xcalibur _computing_data_collection 'Xcalibur (Oxford Diffraction Ltd, 2001)' _computing_data_reduction Xcalibur _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1998)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean '0.06 mm' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Kuma KM-4 CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10881 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.43 _diffrn_standards_decay_% none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.152 _refine_diff_density_min -0.197 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 3128 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0345 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.6568P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.0842 _reflns_number_gt 2917 _reflns_number_total 3128 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1607.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2013206 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O21 0.20177(10) 0.20181(8) 0.07671(6) 0.0294(2) Uani d . 1 O O17 0.07631(10) 0.36114(7) 0.10469(5) 0.0249(2) Uani d . 1 O O14 -0.03387(10) 0.06219(8) 0.09141(5) 0.0253(2) Uani d . 1 O O20 0.07771(11) 0.37934(8) -0.04304(5) 0.0291(2) Uani d . 1 O O13 0.14173(11) 0.03358(8) 0.20015(5) 0.0325(2) Uani d . 1 O C19 0.17067(14) 0.44126(10) -0.00189(7) 0.0212(3) Uani d . 1 C C12 0.07612(15) -0.00061(11) 0.13881(7) 0.0237(3) Uani d . 1 C C27 0.36278(14) 0.60456(11) 0.01506(7) 0.0215(3) Uani d . 1 C H27A 0.3686 0.6032 0.0687 0.026 Uiso calc R 1 H C16 0.09405(14) 0.24649(11) 0.09478(7) 0.0226(3) Uani d . 1 C C25 0.44048(14) 0.68663(11) -0.09360(8) 0.0249(3) Uani d . 1 C H25A 0.4988 0.7423 -0.1147 0.030 Uiso calc R 1 H C23 0.26109(14) 0.52814(11) -0.11069(7) 0.0239(3) Uani d . 1 C H23A 0.1969 0.4744 -0.1434 0.029 Uiso calc R 1 H C22 0.26760(13) 0.52613(10) -0.03241(7) 0.0203(3) Uani d . 1 C C18 0.18937(14) 0.43551(11) 0.08400(7) 0.0229(3) Uani d . 1 C H18A 0.2929 0.4054 0.1074 0.027 Uiso calc R 1 H H18B 0.1801 0.5153 0.1043 0.027 Uiso calc R 1 H C7 0.22398(15) -0.18940(11) 0.14771(7) 0.0235(3) Uani d . 1 C C1 0.38031(15) -0.16346(11) 0.14962(7) 0.0251(3) Uani d . 1 C C9 0.30239(19) -0.35660(12) 0.22930(8) 0.0351(3) Uani d . 1 C H9A 0.2744 -0.4213 0.2568 0.042 Uiso calc R 1 H C6 0.42717(18) -0.06697(12) 0.11045(8) 0.0334(3) Uani d . 1 C H6A 0.3525 -0.0146 0.0828 0.040 Uiso calc R 1 H C15 -0.04277(15) 0.18251(11) 0.11081(8) 0.0260(3) Uani d . 1 C H15A -0.0450 0.1900 0.1657 0.031 Uiso calc R 1 H H15B -0.1383 0.2172 0.0803 0.031 Uiso calc R 1 H C8 0.18822(17) -0.28402(12) 0.18693(7) 0.0284(3) Uani d . 1 C H8A 0.0835 -0.3012 0.1855 0.034 Uiso calc R 1 H C2 0.49524(16) -0.23851(13) 0.19178(8) 0.0318(3) Uani d . 1 C C24 0.34744(15) 0.60796(11) -0.14101(7) 0.0258(3) Uani d . 1 C H24A 0.3430 0.6089 -0.1946 0.031 Uiso calc R 1 H C11 0.09842(16) -0.11547(11) 0.10185(7) 0.0274(3) Uani d . 1 C H11A 0.0011 -0.1601 0.0934 0.033 Uiso calc R 1 H H11B 0.1217 -0.1000 0.0511 0.033 Uiso calc R 1 H C26 0.44885(14) 0.68438(11) -0.01556(8) 0.0243(3) Uani d . 1 C H26A 0.5139 0.7378 0.0170 0.029 Uiso calc R 1 H C5 0.5789(2) -0.04859(15) 0.11206(10) 0.0477(4) Uani d . 1 C H5A 0.6089 0.0158 0.0850 0.057 Uiso calc R 1 H C10 0.45162(19) -0.33513(13) 0.23132(8) 0.0364(4) Uani d . 1 C H10A 0.5280 -0.3855 0.2596 0.044 Uiso calc R 1 H C4 0.6906(2) -0.12384(16) 0.15323(12) 0.0537(5) Uani d . 1 C H4A 0.7958 -0.1101 0.1537 0.064 Uiso calc R 1 H C3 0.65069(18) -0.21575(16) 0.19223(10) 0.0460(4) Uani d . 1 C H3A 0.7281 -0.2656 0.2203 0.055 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 O21 0.0269(5) 0.0227(5) 0.0416(6) 0.0036(4) 0.0137(4) 0.0035(4) O17 0.0254(5) 0.0194(4) 0.0322(5) -0.0001(4) 0.0114(4) -0.0003(4) O14 0.0259(5) 0.0210(5) 0.0278(5) -0.0003(4) 0.0034(4) 0.0033(4) O20 0.0308(5) 0.0235(5) 0.0302(5) -0.0060(4) 0.0003(4) -0.0015(4) O13 0.0450(6) 0.0270(5) 0.0227(5) 0.0055(4) 0.0013(4) -0.0016(4) C19 0.0207(6) 0.0156(6) 0.0261(6) 0.0040(5) 0.0026(5) -0.0014(5) C12 0.0262(7) 0.0231(6) 0.0224(7) -0.0011(5) 0.0063(5) 0.0037(5) C27 0.0237(6) 0.0197(6) 0.0210(6) 0.0024(5) 0.0045(5) -0.0015(5) C16 0.0253(7) 0.0210(6) 0.0214(6) 0.0024(5) 0.0046(5) 0.0037(5) C25 0.0219(6) 0.0225(6) 0.0313(7) 0.0035(5) 0.0078(5) 0.0055(5) C23 0.0241(6) 0.0230(6) 0.0230(6) 0.0022(5) 0.0012(5) -0.0025(5) C22 0.0196(6) 0.0171(6) 0.0236(6) 0.0046(5) 0.0037(5) -0.0002(5) C18 0.0232(6) 0.0181(6) 0.0281(7) -0.0027(5) 0.0072(5) -0.0008(5) C7 0.0322(7) 0.0200(6) 0.0180(6) 0.0002(5) 0.0045(5) -0.0052(5) C1 0.0323(7) 0.0217(6) 0.0217(6) -0.0005(5) 0.0070(5) -0.0087(5) C9 0.0617(10) 0.0217(7) 0.0214(7) 0.0009(7) 0.0078(6) -0.0006(5) C6 0.0452(8) 0.0246(7) 0.0344(8) -0.0048(6) 0.0170(7) -0.0092(6) C15 0.0254(7) 0.0212(6) 0.0326(7) 0.0018(5) 0.0086(5) 0.0027(5) C8 0.0398(8) 0.0237(7) 0.0225(6) -0.0034(6) 0.0083(6) -0.0047(5) C2 0.0341(8) 0.0304(7) 0.0286(7) 0.0048(6) 0.0016(6) -0.0144(6) C24 0.0270(7) 0.0288(7) 0.0221(6) 0.0056(6) 0.0061(5) 0.0036(5) C11 0.0309(7) 0.0256(7) 0.0240(7) 0.0004(6) 0.0024(5) -0.0023(5) C26 0.0227(6) 0.0195(6) 0.0298(7) 0.0003(5) 0.0039(5) -0.0014(5) C5 0.0556(10) 0.0358(9) 0.0615(11) -0.0196(8) 0.0344(9) -0.0226(8) C10 0.0513(9) 0.0282(7) 0.0248(7) 0.0135(7) -0.0027(6) -0.0056(6) C4 0.0365(9) 0.0492(11) 0.0808(13) -0.0103(8) 0.0242(9) -0.0328(10) C3 0.0335(8) 0.0449(10) 0.0561(10) 0.0056(7) 0.0023(7) -0.0262(8) 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 C16 O17 C18 115.96(10) C12 O14 C15 115.43(10) O20 C19 C22 122.48(11) O20 C19 C18 120.20(11) C22 C19 C18 117.31(10) O13 C12 O14 123.21(12) O13 C12 C11 127.28(12) O14 C12 C11 109.52(11) C26 C27 C22 120.18(12) C26 C27 H27A 119.9 C22 C27 H27A 119.9 O21 C16 O17 125.51(12) O21 C16 C15 125.44(12) O17 C16 C15 109.05(10) C26 C25 C24 120.09(12) C26 C25 H25A 120.0 C24 C25 H25A 120.0 C24 C23 C22 120.16(12) C24 C23 H23A 119.9 C22 C23 H23A 119.9 C23 C22 C27 119.44(12) C23 C22 C19 118.83(11) C27 C22 C19 121.72(11) O17 C18 C19 111.14(10) O17 C18 H18A 109.4 C19 C18 H18A 109.4 O17 C18 H18B 109.4 C19 C18 H18B 109.4 H18A C18 H18B 108.0 C8 C7 C1 119.43(12) C8 C7 C11 119.82(12) C1 C7 C11 120.74(12) C6 C1 C7 122.98(13) C6 C1 C2 118.32(13) C7 C1 C2 118.70(12) C10 C9 C8 120.41(14) C10 C9 H9A 119.8 C8 C9 H9A 119.8 C5 C6 C1 120.48(15) C5 C6 H6A 119.8 C1 C6 H6A 119.8 O14 C15 C16 109.39(10) O14 C15 H15A 109.8 C16 C15 H15A 109.8 O14 C15 H15B 109.8 C16 C15 H15B 109.8 H15A C15 H15B 108.2 C7 C8 C9 121.50(14) C7 C8 H8A 119.2 C9 C8 H8A 119.2 C10 C2 C3 121.31(15) C10 C2 C1 119.44(13) C3 C2 C1 119.25(15) C23 C24 C25 120.10(12) C23 C24 H24A 119.9 C25 C24 H24A 119.9 C7 C11 C12 113.96(11) C7 C11 H11A 108.8 C12 C11 H11A 108.8 C7 C11 H11B 108.8 C12 C11 H11B 108.8 H11A C11 H11B 107.7 C27 C26 C25 120.01(12) C27 C26 H26A 120.0 C25 C26 H26A 120.0 C6 C5 C4 120.54(16) C6 C5 H5A 119.7 C4 C5 H5A 119.7 C9 C10 C2 120.51(13) C9 C10 H10A 119.7 C2 C10 H10A 119.7 C3 C4 C5 120.74(15) C3 C4 H4A 119.6 C5 C4 H4A 119.6 C4 C3 C2 120.66(16) C4 C3 H3A 119.7 C2 C3 H3A 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O21 C16 1.1930(16) O17 C16 1.3345(16) O17 C18 1.4274(15) O14 C12 1.3548(16) O14 C15 1.4227(16) O20 C19 1.2103(15) O13 C12 1.1914(16) C19 C22 1.4795(18) C19 C18 1.5095(18) C12 C11 1.5005(18) C27 C26 1.3790(18) C27 C22 1.3896(17) C27 H27A 0.9500 C16 C15 1.5029(18) C25 C26 1.3809(19) C25 C24 1.3818(19) C25 H25A 0.9500 C23 C24 1.3779(19) C23 C22 1.3880(18) C23 H23A 0.9500 C18 H18A 0.9900 C18 H18B 0.9900 C7 C8 1.3626(18) C7 C1 1.4198(19) C7 C11 1.4975(18) C1 C6 1.4159(19) C1 C2 1.4211(19) C9 C10 1.347(2) C9 C8 1.402(2) C9 H9A 0.9500 C6 C5 1.365(2) C6 H6A 0.9500 C15 H15A 0.9900 C15 H15B 0.9900 C8 H8A 0.9500 C2 C10 1.409(2) C2 C3 1.410(2) C24 H24A 0.9500 C11 H11A 0.9900 C11 H11B 0.9900 C26 H26A 0.9500 C5 C4 1.399(3) C5 H5A 0.9500 C10 H10A 0.9500 C4 C3 1.349(3) C4 H4A 0.9500 C3 H3A 0.9500