#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/04/2000410.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_2000410 loop_ _publ_author_name 'Ferguson, G.' 'Ruhl, B. L.' 'McKervey, M. A.' 'Browne, C. M.' _publ_section_title ; Bis(5-chloro-2-hydroxy-1,3-xylyl)-18-crown-4 ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2262 _journal_page_last 2264 _journal_paper_doi 10.1107/S0108270192007832 _journal_volume 48 _journal_year 1992 _chemical_formula_moiety 'C20 H22 Cl2 O6 ' _chemical_formula_sum 'C20 H22 Cl2 O6' _chemical_formula_weight 429.29 _chemical_name_systematic ; Bis(5-chloro-2-hydroxy-1,3-xylyl)-18-crown-4 ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2bc 2ac' _symmetry_space_group_name_H-M 'P c a b' _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 6.5779(15) _cell_length_b 15.5650(13) _cell_length_c 19.217(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 25.00 _cell_measurement_theta_min 20.00 _cell_volume 1967.5(5) _computing_cell_refinement 'Enraf-Nonius CAD4 system' _computing_data_collection 'Enraf-Nonius CAD4 system' _computing_data_reduction 'NRCVAX DATRD2' _computing_molecular_graphics NRCVAX _computing_publication_material 'NRCVAX TABLES' _computing_structure_refinement 'NRCVAX LSTSQ' _computing_structure_solution 'NRCVAX SOLVER' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Nonius CAD-4 ' _diffrn_measurement_method '\q/2\q scan b/P/b ' _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 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2149 _diffrn_reflns_theta_max 26.94 _diffrn_reflns_theta_min 2.00 _diffrn_standards_decay_% +-1.0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.36 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.449 _exptl_crystal_description plate _exptl_crystal_F_000 897.41 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.33 _refine_diff_density_max 0.21 _refine_diff_density_min -0.20 _refine_ls_goodness_of_fit_obs 1.09 _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1171 _refine_ls_R_factor_obs 0.0427 _refine_ls_shift/esd_max 0.03 _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_obs 0.0373 _reflns_number_observed 1171 _reflns_number_total 2149 _reflns_observed_criterion 'Inet > 3.0\s(Inet)' _[local]_cod_data_source_file li1019.cif _[local]_cod_data_source_block CLPHO6 _[local]_cod_chemical_formula_sum_orig 'C20 H22 Cl2 O6 ' _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. '_refine_ls_matrix_type' value 'Full' changed to 'full' 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. '_refine_ls_matrix_type' value 'Full' changed to 'full' 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_original_cell_volume 1967.6(5) _cod_database_code 2000410 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 1/2-x,y,1/2+z 1/2+x,-y,1/2-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 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 0.0984(7) 0.0636(6) 0.0824(7) -0.0052(6) 0.0742(6) 0.0371(6) Cl O1 0.0511(13) 0.0395(12) 0.0874(17) 0.0025(11) 0.0299(13) 0.0148(12) O O2 0.0528(13) 0.0388(12) 0.0662(14) 0.0041(11) 0.0009(12) -0.0039(11) O O3 0.0499(13) 0.0404(11) 0.0719(15) 0.0130(10) 0.0252(12) 0.0029(11) O C1 0.0448(19) 0.0410(17) 0.0446(17) -0.0095(16) -0.0074(16) -0.0020(15) C C2 0.048(2) 0.0431(17) 0.0435(17) 0.0040(16) -0.0012(16) -0.0173(15) C C3 0.050(2) 0.0548(19) 0.0355(16) 0.0026(16) 0.0102(17) -0.0117(15) C C4 0.056(2) 0.0461(17) 0.0378(16) -0.0074(17) 0.0045(16) 0.0008(15) C C5 0.055(2) 0.0384(16) 0.0413(17) 0.0044(16) -0.0088(16) -0.0061(14) C C6 0.0416(19) 0.0390(16) 0.0430(17) 0.0009(15) -0.0082(15) -0.0097(15) C C7 0.068(2) 0.051(2) 0.049(2) 0.0245(18) 0.0075(18) -0.0136(16) C C8 0.0427(19) 0.0371(17) 0.071(2) -0.0033(14) 0.0044(17) -0.0086(17) C C9 0.0395(18) 0.0531(19) 0.064(2) -0.0044(16) 0.0115(17) -0.0085(17) C C10 0.046(2) 0.056(2) 0.069(2) 0.0325(17) 0.0051(17) 0.0166(19) C 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 0.13443(15) 0.32911(6) 0.73618(5) 0.08153 Uani ? . Cl O(1) 0.5434(3) 0.59813(12) 0.57668(11) 0.05939 Uani ? . O O(2) 0.1820(3) 0.68462(11) 0.58317(10) 0.05267 Uani ? . O O(3) 0.7299(3) 0.34843(12) 0.56061(10) 0.05411 Uani ? . O C(1) 0.4422(4) 0.53708(18) 0.61435(14) 0.04351 Uani ? . C C(2) 0.2652(5) 0.55617(18) 0.65125(14) 0.04499 Uani ? . C C(3) 0.1703(4) 0.49178(19) 0.68887(14) 0.04665 Uani ? . C C(4) 0.2549(5) 0.41090(17) 0.68970(14) 0.04668 Uani ? . C C(5) 0.4297(5) 0.39144(17) 0.65346(14) 0.04491 Uani ? . C C(6) 0.5262(4) 0.45472(17) 0.61502(14) 0.04125 Uani ? . C C(7) 0.1804(5) 0.64641(19) 0.65119(15) 0.05630 Uani ? . C C(8) 0.7160(5) 0.43719(17) 0.57396(16) 0.05037 Uani ? . C C(9) 0.0337(5) 0.64844(19) 0.53708(16) 0.05237 Uani ? . C C(10) 0.9233(5) 0.32167(19) 0.53472(16) 0.05715 Uani ? . C H(O1) 0.445 0.653 0.569 0.0600 Uiso ? . H H(3) 0.024 0.513 0.722 0.0600 Uiso ? . H H(5) 0.492 0.329 0.652 0.0600 Uiso ? . H H(71) 0.023 0.645 0.676 0.0600 Uiso ? . H H(72) 0.264 0.691 0.685 0.0600 Uiso ? . H H(81) 0.711 0.479 0.531 0.0600 Uiso ? . H H(82) 0.844 0.468 0.600 0.0600 Uiso ? . H H(91) 0.027 0.583 0.537 0.0600 Uiso ? . H H(92) -0.109 0.662 0.559 0.0600 Uiso ? . H H(101) 0.916 0.253 0.542 0.0600 Uiso ? . H H(102) 1.045 0.342 0.566 0.0600 Uiso ? . 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 0 10 0 12 0 4 0 0 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(1) O(1) H(O1) . . . 109.5 no C(7) O(2) C(9) . . . 113.3(2) yes C(8) O(3) C(10) . . . 114.1(2) yes O(1) C(1) C(2) . . . 121.8(3) yes O(1) C(1) C(6) . . . 116.8(3) yes C(2) C(1) C(6) . . . 121.4(3) yes C(1) C(2) C(3) . . . 119.2(3) yes C(1) C(2) C(7) . . . 120.4(3) yes C(3) C(2) C(7) . . . 120.4(3) yes C(2) C(3) C(4) . . . 119.1(3) yes C(2) C(3) H(3) . . . 116.3 no C(4) C(3) H(3) . . . 124.5 no Cl C(4) C(3) . . . 119.3(2) yes Cl C(4) C(5) . . . 118.5(2) yes C(3) C(4) C(5) . . . 122.2(3) yes C(4) C(5) C(6) . . . 119.7(3) yes C(4) C(5) H(5) . . . 122.8 no C(6) C(5) H(5) . . . 117.5 no C(1) C(6) C(5) . . . 118.5(3) yes C(1) C(6) C(8) . . . 119.4(2) yes C(5) C(6) C(8) . . . 122.1(2) yes O(2) C(7) C(2) . . . 112.5(2) yes O(2) C(7) H(71) . . . 113.1 no O(2) C(7) H(72) . . . 105.7 no C(2) C(7) H(71) . . . 108.6 no C(2) C(7) H(72) . . . 113.7 no H(71) C(7) H(72) . . . 102.9 no O(3) C(8) C(6) . . . 109.2(2) yes O(3) C(8) H(81) . . . 118.3 no O(3) C(8) H(82) . . . 117.4 no C(6) C(8) H(81) . . . 105.6 no C(6) C(8) H(82) . . . 108.5 no H(81) C(8) H(82) . . . 96.7 no O(2) C(9) C(10) . . 2_666 108.8(2) yes O(2) C(9) H(91) . . . 115.4 no O(2) C(9) H(92) . . . 106.1 no C(10) C(9) H(91) 2_666 . . 108.4 no C(10) C(9) H(92) 2_666. . . 118.7 no H(91) C(9) H(92) . . . 99.7 no O(3) C(10) C(9) . . 2_666 113.7(2) yes O(3) C(10) H(101) . . . 101.8 no O(3) C(10) H(102) . . . 113.2 no C(9) C(10) H(101) 2_666. . . 115.7 no C(9) C(10) H(102) 2_666. . . 107.1 no H(101) C(10) H(102) . . . 105.1 no O(1) H(O1) O(2) . . . 139.0 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) . . 1.745(3) yes O(1) C(1) . . 1.368(3) yes O(1) H(O1) . . 1.09 no O(2) C(7) . . 1.436(3) yes O(2) C(9) . . 1.433(4) yes O(3) C(8) . . 1.408(3) yes O(3) C(10) . . 1.428(4) yes C(1) C(2) . . 1.395(4) yes C(1) C(6) . . 1.396(4) yes C(2) C(3) . . 1.385(4) yes C(2) C(7) . . 1.511(4) yes C(3) C(4) . . 1.377(4) yes C(3) H(3) . . 1.20 no C(4) C(5) . . 1.378(4) yes C(5) C(6) . . 1.385(4) yes C(5) H(5) . . 1.05 no C(6) C(8) . . 1.502(4) yes C(7) H(71) . . 1.14 no C(7) H(72) . . 1.09 no C(8) H(81) . . 1.05 no C(8) H(82) . . 1.09 no C(9) C(10) . 2_666 1.483(4) yes C(9) H(91) . . 1.02 no C(9) H(92) . . 1.05 no C(10) H(101) . . 1.08 no C(10) H(102) . . 1.05 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(1) O(2) 2.735(3) . . yes H(O1) O(2) 1.82 . . 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 C(9) O(2) C(7) C(2) . . . . 71.8(2) yes C(7) O(2) C(9) C(10) . . . 2_666 -168.0(3) yes C(10) O(3) C(8) C(6) . . . . -167.7(3) yes C(8) O(3) C(10) C(9) . . . 2_666 -69.7(2) yes O(1) C(1) C(2) C(3) . . . . -179.5(4) no O(1) C(1) C(2) C(7) . . . . -0.60(10) no C(6) C(1) C(2) C(3) . . . . -0.5(2) no C(6) C(1) C(2) C(7) . . . . 178.4(4) no O(1) C(1) C(6) C(5) . . . . 179.0(4) no O(1) C(1) C(6) C(8) . . . . -1.40(10) no C(2) C(1) C(6) C(5) . . . . 0.0(2) no C(2) C(1) C(6) C(8) . . . . 179.5(3) no C(1) C(2) C(3) C(4) . . . . 1.0(2) no C(7) C(2) C(3) C(4) . . . . -177.9(4) no C(1) C(2) C(7) O(2) . . . . 43.9(2) yes C(3) C(2) C(7) O(2) . . . . -137.2(3) no C(2) C(3) C(4) Cl . . . . -179.3(3) no C(2) C(3) C(4) C(5) . . . . -1.0(2) no Cl C(4) C(5) C(6) . . . . 178.7(3) no C(3) C(4) C(5) C(6) . . . . 0.4(2) no C(4) C(5) C(6) C(1) . . . . 0.1(2) no C(4) C(5) C(6) C(8) . . . . -179.4(4) no C(1) C(6) C(8) O(3) . . . . -158.2(3) yes C(5) C(6) C(8) O(3) . . . . 21.3(2) no O(2) C(9) C(10) O(3) . . 2_666 2_666 62.1(2) yes