#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/21/2002108.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_2002108 loop_ _publ_author_name 'Ferguson, G.' 'Kaitner, B.' 'McKervey, M. A.' 'Owens, M.' _publ_section_title ; 5-Chloro-2-hydroxycarbonylmethoxy-1,3-xylyl-18-crown-5 and 5-chloro-2-ethoxycarbonylmethoxy-1,3-xylyl-18-crown-5 ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 179 _journal_page_last 182 _journal_paper_doi 10.1107/S0108270192009971 _journal_volume 49 _journal_year 1993 _chemical_formula_moiety 'C18 H25 Cl O8 ' _chemical_formula_sum 'C18 H25 Cl O8' _chemical_formula_weight 404.84 _chemical_name_systematic ; 5-chloro-2-hydroxycarbonylmethoxy-1,3-xylyl-18-crown-5 ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_formula_units_Z 8 _cell_length_a 13.856(2) _cell_length_b 18.783(4) _cell_length_c 15.209(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 15.00 _cell_measurement_theta_min 10.00 _cell_volume 3958.3(11) _computing_cell_refinement 'Enraf-Nonius CAD-4 software' _computing_data_collection 'Enraf-Nonius CAD-4 software' _computing_data_reduction 'NRCVAX DATRD2 (Gabe, Le Page, Charland, Lee & White, 1989)' _computing_molecular_graphics 'NRCVAX (Gabe et al., 1989)' _computing_publication_material 'NRCVAX TABLES (Gabe et al., 1989)' _computing_structure_refinement 'NRCVAX LSTSQ (Gabe et al., 1989)' _computing_structure_solution 'NRCVAX SOLVER (Gabe et al., 1989)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Enraf-Nonius CAD-4 ' _diffrn_measurement_method ;\q/2\q scans [\q-scan width (0.6 + 0.35tan\q)\%, \q-scan rate 3.3\% min^-1^, background counts for 15 s on each side of every scan] ; _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'xray tube' _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_wavelength 0.70930 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4301 _diffrn_reflns_theta_max 26.92 _diffrn_reflns_theta_min 0.00 _diffrn_standards_decay_% '< 1.0' _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.23 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.359 _exptl_crystal_description needle _exptl_crystal_F_000 1712 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.20 _refine_diff_density_min -0.21 _refine_ls_extinction_coef 473E1(2) _refine_ls_extinction_method 'Larson (1970)' _refine_ls_goodness_of_fit_obs 1.24 _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 1930 _refine_ls_R_factor_all 0.112 _refine_ls_R_factor_obs 0.036 _refine_ls_shift/esd_max 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F)+0.0008F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.059 _refine_ls_wR_factor_obs 0.048 _reflns_number_observed 1930 _reflns_number_total 4301 _reflns_observed_criterion 'Inet > 3.0\s(Inet)' _[local]_cod_data_source_file br1013.cif _[local]_cod_data_source_block br1013_structure_1_of_2 _[local]_cod_chemical_formula_sum_orig 'C18 H25 Cl O8 ' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(F)+0.0008F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F)+0.0008F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2002108 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 1/2-x,1/2+y,z 1/2+x,1/2-y,-z x,1/2-y,1/2+z -x,1/2+y,1/2-z 1/2-x,-y,1/2+z 1/2+x,y,1/2-z 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 _atom_site_aniso_type_symbol Cl 0.1027(7) 0.0641(5) 0.0723(6) -0.0007(10) 0.0403(10) -0.0476(8) Cl C1 0.0434(15) 0.0478(16) 0.0435(14) 0.008(3) -0.022(3) -0.004(3) C C2 0.0427(15) 0.0471(16) 0.0421(16) -0.009(3) -0.017(3) -0.004(3) C C3 0.0615(19) 0.0423(15) 0.0449(16) -0.011(3) -0.019(3) -0.005(3) C C4 0.0611(19) 0.0497(17) 0.0413(16) 0.003(3) -0.007(3) -0.016(3) C C5 0.0563(18) 0.0604(19) 0.0395(15) -0.011(3) -0.001(3) 0.002(3) C C6 0.0494(17) 0.0468(16) 0.0434(15) -0.006(3) -0.024(3) 0.010(3) C C7 0.064(2) 0.0528(17) 0.0577(19) -0.011(3) -0.023(3) 0.021(3) C O8 0.0509(11) 0.0430(10) 0.0612(11) 0.0025(18) -0.007(2) 0.0046(18) O C9 0.0480(17) 0.0544(17) 0.0593(18) 0.001(3) 0.013(3) 0.002(3) C C10 0.0469(17) 0.0564(18) 0.069(2) -0.012(3) 0.005(3) 0.002(3) C O11 0.0505(11) 0.0552(12) 0.0520(11) -0.0199(19) 0.0005(19) -0.0033(19) O C12 0.0533(18) 0.0621(19) 0.0611(19) -0.008(3) -0.012(3) -0.022(3) C C13 0.061(2) 0.0600(19) 0.0573(19) 0.013(3) -0.020(3) -0.011(3) C O14 0.0574(12) 0.0511(11) 0.0517(12) -0.0017(19) -0.002(2) -0.0004(19) O C15 0.083(2) 0.064(2) 0.0489(17) -0.017(4) 0.011(4) -0.018(3) C C16 0.090(3) 0.071(2) 0.0483(18) -0.032(4) 0.000(4) 0.016(3) C O17 0.0783(15) 0.0519(12) 0.0556(12) -0.016(2) 0.000(2) -0.011(2) O C18 0.082(2) 0.0563(19) 0.0481(17) -0.020(3) 0.034(3) 0.002(3) C C19 0.069(2) 0.0549(18) 0.0613(19) -0.025(3) 0.049(4) -0.008(3) C O20 0.0501(11) 0.0592(12) 0.0455(11) -0.0191(19) 0.0145(19) -0.0029(18) O C21 0.0502(17) 0.0564(18) 0.0567(19) -0.019(3) -0.004(3) -0.006(3) C O22 0.0447(11) 0.0552(12) 0.0656(12) 0.0205(18) -0.021(2) -0.027(2) O C23 0.0460(16) 0.0447(16) 0.0521(16) 0.008(3) 0.004(3) -0.007(3) C C24 0.0361(15) 0.0477(16) 0.0626(19) 0.003(3) 0.003(3) -0.004(3) C O25 0.0665(14) 0.0543(13) 0.0874(16) 0.027(2) -0.045(2) 0.010(2) O O26 0.0618(13) 0.0442(12) 0.0733(14) 0.015(2) -0.021(3) -0.010(2) O loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol Cl 0.50333(7) 0.89173(4) 0.60044(6) 0.0797(5) Uani ? . Cl C1 0.35520(19) 1.06334(14) 0.75566(17) 0.0449(14) Uani ? . C C2 0.33193(19) 0.99214(14) 0.77150(17) 0.0440(14) Uani ? . C C3 0.3768(2) 0.94001(14) 0.72211(17) 0.0496(16) Uani ? . C C4 0.4439(2) 0.95809(15) 0.65933(17) 0.0507(16) Uani ? . C C5 0.4668(2) 1.02842(15) 0.64367(18) 0.0521(16) Uani ? . C C6 0.4221(2) 1.08182(14) 0.69149(18) 0.0465(15) Uani ? . C C7 0.4461(2) 1.15886(16) 0.67325(19) 0.0582(17) Uani ? . C O8 0.49328(14) 1.19327(9) 0.74421(14) 0.0517(11) Uani ? . O C9 0.5876(2) 1.16658(15) 0.76058(19) 0.0539(17) Uani ? . C C10 0.6274(2) 1.20324(15) 0.8395(2) 0.0574(18) Uani ? . C O11 0.57928(13) 1.17780(9) 0.91546(12) 0.0526(11) Uani ? . O C12 0.6084(2) 1.21292(16) 0.9936(2) 0.0588(17) Uani ? . C C13 0.5644(2) 1.17673(15) 1.07095(19) 0.0593(18) Uani ? . C O14 0.46227(14) 1.18589(9) 1.06965(12) 0.0534(11) Uani ? . O C15 0.4145(2) 1.15934(17) 1.14635(19) 0.0653(19) Uani ? . C C16 0.4016(3) 1.08075(17) 1.1466(2) 0.070(2) Uani ? . C O17 0.33303(15) 1.06211(10) 1.08145(12) 0.0619(12) Uani ? . O C18 0.3186(2) 0.98798(15) 1.0771(2) 0.0623(19) Uani ? . C C19 0.2579(2) 0.97177(16) 1.00013(19) 0.0618(18) Uani ? . C O20 0.31356(13) 0.98347(9) 0.92366(12) 0.0516(10) Uani ? . O C21 0.2630(2) 0.97313(15) 0.84338(19) 0.0545(17) Uani ? . C O22 0.30339(13) 1.11582(9) 0.79835(13) 0.0552(11) Uani ? . O C23 0.34527(19) 1.14527(14) 0.87641(18) 0.0476(15) Uani ? . C C24 0.3259(2) 1.22368(15) 0.8785(2) 0.0488(16) Uani ? . C O25 0.28043(15) 1.25648(10) 0.82499(15) 0.0694(13) Uani ? . O O26 0.36141(15) 1.25680(11) 0.94949(16) 0.0598(13) Uani ? . O H(O26) 0.393(2) 1.2280(17) 0.981(2) 0.088(13) Uiso ? . H H3 0.361 0.891 0.732 0.0596 Uiso calc . H H5 0.513 1.040 0.600 0.0620 Uiso calc . H H7A 0.388 1.184 0.661 0.0682 Uiso calc . H H7B 0.487 1.161 0.623 0.0682 Uiso calc . H H9A 0.585 1.117 0.771 0.0639 Uiso calc . H H9B 0.628 1.176 0.711 0.0639 Uiso calc . H H10A 0.618 1.253 0.834 0.0674 Uiso calc . H H10B 0.694 1.194 0.844 0.0674 Uiso calc . H H12A 0.677 1.211 0.998 0.0688 Uiso calc . H H12B 0.588 1.261 0.992 0.0688 Uiso calc . H H13A 0.590 1.197 1.123 0.0693 Uiso calc . H H13B 0.579 1.127 1.069 0.0693 Uiso calc . H H15A 0.452 1.172 1.196 0.0753 Uiso calc . H H15B 0.353 1.181 1.150 0.0753 Uiso calc . H H16A 0.379 1.066 1.203 0.0796 Uiso calc . H H16B 0.461 1.058 1.134 0.0796 Uiso calc . H H18A 0.379 0.965 1.071 0.0723 Uiso calc . H H18B 0.287 0.972 1.129 0.0723 Uiso calc . H H19A 0.203 1.002 1.000 0.0718 Uiso calc . H H19B 0.238 0.924 1.002 0.0718 Uiso calc . H H21A 0.243 0.925 0.838 0.0645 Uiso calc . H H21B 0.208 1.003 0.841 0.0645 Uiso calc . H H23A 0.317 1.123 0.927 0.0576 Uiso calc . H H23B 0.413 1.137 0.876 0.0576 Uiso calc . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 'International Tables Vol. IV Table 2.2B' H ? 0.000 0.000 'International Tables Vol. IV Table 2.2B' Cl ? 0.132 0.159 'International Tables Vol. IV Table 2.2B' O ? 0.008 0.006 'International Tables Vol. IV Table 2.2B' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 12 3 8 1 1 1 9 1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C(2) C(1) C(6) . . . 120.9(3) no C(2) C(1) O(22) . . . 118.8(2) no C(6) C(1) O(22) . . . 119.9(2) no C(1) C(2) C(3) . . . 118.8(3) no C(1) C(2) C(21) . . . 120.2(2) no C(3) C(2) C(21) . . . 121.1(2) no C(2) C(3) C(4) . . . 120.4(2) no Cl C(4) C(3) . . . 120.0(2) no Cl C(4) C(5) . . . 119.2(2) no C(3) C(4) C(5) . . . 120.8(3) no C(4) C(5) C(6) . . . 120.0(3) no C(1) C(6) C(5) . . . 119.1(2) no C(1) C(6) C(7) . . . 121.0(3) no C(5) C(6) C(7) . . . 120.0(3) no C(6) C(7) O(8) . . . 113.5(2) no C(7) O(8) C(9) . . . 113.4(2) no O(8) C(9) C(10) . . . 108.6(2) no C(9) C(10) O(11) . . . 109.1(2) no C(10) O(11) C(12) . . . 113.1(2) no O(11) C(12) C(13) . . . 109.4(2) no C(12) C(13) O(14) . . . 109.9(2) no C(13) O(14) C(15) . . . 113.9(2) no O(14) C(15) C(16) . . . 113.8(2) no C(15) C(16) O(17) . . . 108.9(3) no C(16) O(17) C(18) . . . 111.9(2) no O(17) C(18) C(19) . . . 108.8(3) no C(18) C(19) O(20) . . . 108.1(3) no C(19) O(20) C(21) . . . 114.6(2) no C(2) C(21) O(20) . . . 106.3(2) no C(1) O(22) C(23) . . . 117.03(19) no O(22) C(23) C(24) . . . 108.9(2) no C(23) C(24) O(25) . . . 125.8(3) no C(23) C(24) O(26) . . . 114.1(3) no O(25) C(24) O(26) . . . 120.1(3) no C(24) O(26) H(O26) . . . 111.(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl C(4) . . 1.742(3) no C(1) C(2) . . 1.397(4) no C(1) C(6) . . 1.390(4) no C(1) O(22) . . 1.381(3) no C(2) C(3) . . 1.382(4) no C(2) C(21) . . 1.495(4) no C(3) C(4) . . 1.376(4) no C(4) C(5) . . 1.379(4) no C(5) C(6) . . 1.385(4) no C(6) C(7) . . 1.510(4) no C(7) O(8) . . 1.418(4) no O(8) C(9) . . 1.421(3) no C(9) C(10) . . 1.489(4) no C(10) O(11) . . 1.417(3) no O(11) C(12) . . 1.418(3) no C(12) C(13) . . 1.490(4) no C(13) O(14) . . 1.425(4) no O(14) C(15) . . 1.431(4) no C(15) C(16) . . 1.487(5) no C(16) O(17) . . 1.416(4) no O(17) C(18) . . 1.408(3) no C(18) C(19) . . 1.474(5) no C(19) O(20) . . 1.413(3) no O(20) C(21) . . 1.421(3) no O(22) C(23) . . 1.433(3) no C(23) C(24) . . 1.497(4) no C(24) O(25) . . 1.199(4) no C(24) O(26) . . 1.340(4) no O(26) H(O26) . . 0.85(3) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(26) O(14) 2.658(3) . . no H(O26) O(14) 1.83(3) . . no 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 C3 . . . . 0.0(2) no C6 C1 C2 C21 . . . . 177.4(3) no O22 C1 C2 C3 . . . . 173.4(3) no O22 C1 C2 C21 . . . . -9.30(10) no C2 C1 C6 C5 . . . . -0.7(2) no C2 C1 C6 C7 . . . . 178.9(3) no O22 C1 C6 C5 . . . . -174.0(3) no O22 C1 C6 C7 . . . . 5.70(10) no C2 C1 O22 C23 . . . . 97.4(2) no C6 C1 O22 C23 . . . . -89.2(2) no C1 C2 C3 C4 . . . . 0.8(2) no C21 C2 C3 C4 . . . . -176.5(3) no C1 C2 C21 O20 . . . . -73.4(2) no C3 C2 C21 O20 . . . . 103.9(3) no C2 C3 C4 CL . . . . 177.6(3) no C2 C3 C4 C5 . . . . -0.9(2) no CL C4 C5 C6 . . . . -178.3(3) no C3 C4 C5 C6 . . . . 0.2(2) no C4 C5 C6 C1 . . . . 0.6(2) no C4 C5 C6 C7 . . . . -179.0(3) no C1 C6 C7 O8 . . . . 66.2(2) no C5 C6 C7 O8 . . . . -114.1(3) no C6 C7 O8 C9 . . . . 67.2(2) no C7 O8 C9 C10 . . . . -176.5(3) no O8 C9 C10 O11 . . . . 72.1(2) no C9 C10 O11 C12 . . . . -176.4(3) no C10 O11 C12 C13 . . . . -172.6(3) no O11 C12 C13 O14 . . . . -66.6(2) no C12 C13 O14 C15 . . . . -173.8(3) no C13 O14 C15 C16 . . . . -78.7(3) no O14 C15 C16 O17 . . . . -69.4(2) no C15 C16 O17 C18 . . . . 179.0(4) no C16 O17 C18 C19 . . . . -171.8(3) no O17 C18 C19 O20 . . . . 71.0(2) no C18 C19 O20 C21 . . . . -177.2(3) no C19 O20 C21 C2 . . . . 176.7(3) no C1 O22 C23 C24 . . . . 141.3(3) no O22 C23 C24 O25 . . . . 2.00(10) no O22 C23 C24 O26 . . . . 179.5(3) no