#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013249.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_2013249 loop_ _publ_author_name 'Dielemann, Cedric' 'Matt, Dominique' 'Jones, Peter G.' 'Th\"onnessen, Holger' _publ_section_title ; The host--guest complex between cone-25,26:27,28-bis(methylenedioxy)calix[4]arene and dichloromethane ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o247 _journal_page_last o249 _journal_paper_doi 10.1107/S0108270103006681 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C30 H24 O4, C H2 Cl2' _chemical_formula_moiety 'C30 H24 O4, C H2 Cl2' _chemical_formula_sum 'C31 H26 Cl2 O4' _chemical_formula_weight 533.42 _chemical_name_systematic ; cone-25,26:27,28-bis(methylenedioxy)calix[4]arene dichloromethane solvate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/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 111.490(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 16.042(2) _cell_length_b 9.4781(10) _cell_length_c 17.599(2) _cell_measurement_reflns_used 64 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27 _cell_measurement_theta_min 8 _cell_volume 2489.9(5) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Fait, 1991)' _computing_data_reduction XSCANS _computing_molecular_graphics 'XP (Siemens, 1994)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Siemens P4' _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 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 3350 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.05 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 247 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1112 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.5 _refine_diff_density_max 0.22 _refine_diff_density_min -0.39 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 2173 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0347 _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^)+(0.0493P)^2^+1.8139P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0896 _refine_ls_wR_factor_ref 0.0925 _reflns_number_gt 1894 _reflns_number_total 2173 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1530.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2013249 _cod_database_fobs_code 2013249 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 -0.03403(7) 0.42569(11) 0.31439(6) 0.0280(3) Uani d . 1 . . O O2 0.11689(7) 0.49167(10) 0.37375(6) 0.0283(3) Uani d . 1 . . O C1 0.02659(11) 0.53078(16) 0.35714(10) 0.0298(4) Uani d . 1 . . C H1A 0.0185 0.5500 0.4093 0.036 Uiso calc R 1 . . H H1B 0.0132 0.6188 0.3246 0.036 Uiso calc R 1 . . H C11 -0.08144(10) 0.35402(15) 0.35435(9) 0.0237(3) Uani d . 1 . . C C12 -0.17184(10) 0.33321(15) 0.30808(9) 0.0239(3) Uani d . 1 . . C C13 -0.22337(10) 0.25816(16) 0.34289(9) 0.0262(3) Uani d . 1 . . C H13 -0.2853 0.2433 0.3125 0.031 Uiso calc R 1 . . H C14 -0.18526(11) 0.20460(16) 0.42173(9) 0.0285(4) Uani d . 1 . . C H14 -0.2210 0.1539 0.4452 0.034 Uiso calc R 1 . . H C15 -0.09503(11) 0.22573(16) 0.46581(9) 0.0272(3) Uani d . 1 . . C H15 -0.0695 0.1884 0.5195 0.033 Uiso calc R 1 . . H C16 -0.04048(10) 0.30035(15) 0.43361(9) 0.0247(3) Uani d . 1 . . C C17 0.05941(10) 0.31391(16) 0.48318(9) 0.0271(3) Uani d . 1 . . C H17A 0.0734 0.4140 0.4987 0.032 Uiso calc R 1 . . H H17B 0.0739 0.2585 0.5341 0.032 Uiso calc R 1 . . H C21 0.14032(10) 0.34996(15) 0.38371(8) 0.0235(3) Uani d . 1 . . C C22 0.11842(9) 0.26379(16) 0.43802(8) 0.0243(3) Uani d . 1 . . C C23 0.15267(10) 0.12747(17) 0.45113(9) 0.0274(3) Uani d . 1 . . C H23 0.1387 0.0676 0.4881 0.033 Uiso calc R 1 . . H C24 0.20676(10) 0.07750(17) 0.41129(9) 0.0305(4) Uani d . 1 . . C H24 0.2310 -0.0151 0.4219 0.037 Uiso calc R 1 . . H C25 0.22533(10) 0.16301(17) 0.35598(9) 0.0280(3) Uani d . 1 . . C H25 0.2615 0.1277 0.3279 0.034 Uiso calc R 1 . . H C26 0.19200(9) 0.30025(16) 0.34045(8) 0.0242(3) Uani d . 1 . . C C27 0.21231(10) 0.39104(17) 0.27827(9) 0.0275(3) Uani d . 1 . . C H27A 0.2781 0.3982 0.2940 0.033 Uiso calc R 1 . . H H27B 0.1888 0.4873 0.2793 0.033 Uiso calc R 1 . . H C99 0.0000 0.0455(3) 0.2500 0.0362(5) Uani d S 1 . . C H99 -0.0486 0.1070 0.2146 0.043 Uiso d R 1 . . H Cl -0.04111(4) -0.05813(7) 0.31110(4) 0.0704(2) Uani d . 1 . . Cl 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 O1 0.0285(6) 0.0328(6) 0.0256(5) -0.0035(5) 0.0132(4) 0.0018(4) O2 0.0294(6) 0.0220(5) 0.0357(6) -0.0041(4) 0.0147(5) -0.0064(4) C1 0.0345(8) 0.0218(7) 0.0381(8) 0.0005(6) 0.0193(7) -0.0013(6) C11 0.0290(8) 0.0214(7) 0.0253(7) 0.0014(6) 0.0155(6) -0.0012(6) C12 0.0280(8) 0.0209(7) 0.0253(7) 0.0050(6) 0.0127(6) -0.0006(6) C13 0.0262(8) 0.0245(7) 0.0296(8) 0.0006(6) 0.0121(6) -0.0025(6) C14 0.0352(9) 0.0245(8) 0.0307(8) -0.0031(6) 0.0181(7) 0.0002(6) C15 0.0354(8) 0.0264(8) 0.0217(7) 0.0009(7) 0.0126(6) 0.0000(6) C16 0.0304(8) 0.0224(7) 0.0233(7) 0.0006(6) 0.0122(6) -0.0041(6) C17 0.0309(8) 0.0302(8) 0.0209(7) -0.0020(6) 0.0104(6) -0.0031(6) C21 0.0226(7) 0.0232(7) 0.0214(7) -0.0031(6) 0.0044(6) -0.0063(6) C22 0.0228(7) 0.0286(8) 0.0180(7) -0.0030(6) 0.0033(6) -0.0055(6) C23 0.0284(8) 0.0303(8) 0.0193(7) -0.0014(6) 0.0038(6) -0.0003(6) C24 0.0304(8) 0.0301(8) 0.0244(7) 0.0058(7) 0.0024(6) -0.0016(6) C25 0.0243(8) 0.0349(8) 0.0220(7) 0.0029(6) 0.0051(6) -0.0067(6) C26 0.0196(7) 0.0290(8) 0.0204(7) -0.0051(6) 0.0033(6) -0.0068(6) C27 0.0241(7) 0.0304(8) 0.0295(8) -0.0071(6) 0.0114(6) -0.0066(6) C99 0.0312(12) 0.0349(12) 0.0345(12) 0.000 0.0026(10) 0.000 Cl 0.0486(3) 0.0926(5) 0.0648(4) -0.0202(3) 0.0147(3) 0.0214(3) 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' Cl Cl 0.1484 0.1585 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C11 O1 C1 . . 118.47(11) C21 O2 C1 . . 119.19(11) O1 C1 O2 . . 112.33(12) O1 C1 H1A . . 109.1 O2 C1 H1A . . 109.1 O1 C1 H1B . . 109.1 O2 C1 H1B . . 109.1 H1A C1 H1B . . 107.9 O1 C11 C12 . . 114.81(12) O1 C11 C16 . . 122.53(13) C12 C11 C16 . . 122.58(13) C13 C12 C11 . . 118.31(13) C13 C12 C27 . 2 121.31(13) C11 C12 C27 . 2 120.37(13) C14 C13 C12 . . 120.72(14) C14 C13 H13 . . 119.6 C12 C13 H13 . . 119.6 C15 C14 C13 . . 119.57(14) C15 C14 H14 . . 120.2 C13 C14 H14 . . 120.2 C14 C15 C16 . . 121.88(14) C14 C15 H15 . . 119.1 C16 C15 H15 . . 119.1 C15 C16 C11 . . 116.91(14) C15 C16 C17 . . 119.63(13) C11 C16 C17 . . 123.40(13) C22 C17 C16 . . 113.62(12) C22 C17 H17A . . 108.8 C16 C17 H17A . . 108.8 C22 C17 H17B . . 108.8 C16 C17 H17B . . 108.8 H17A C17 H17B . . 107.7 O2 C21 C22 . . 121.86(13) O2 C21 C26 . . 116.40(13) C22 C21 C26 . . 121.61(14) C23 C22 C21 . . 118.30(13) C23 C22 C17 . . 119.23(13) C21 C22 C17 . . 122.47(13) C24 C23 C22 . . 121.15(14) C24 C23 H23 . . 119.4 C22 C23 H23 . . 119.4 C25 C24 C23 . . 119.58(14) C25 C24 H24 . . 120.2 C23 C24 H24 . . 120.2 C24 C25 C26 . . 121.30(14) C24 C25 H25 . . 119.4 C26 C25 H25 . . 119.4 C25 C26 C21 . . 117.98(14) C25 C26 C27 . . 120.11(13) C21 C26 C27 . . 121.91(13) C26 C27 C12 . 2 112.98(12) C26 C27 H27A . . 109.0 C12 C27 H27A 2 . 109.0 C26 C27 H27B . . 109.0 C12 C27 H27B 2 . 109.0 H27A C27 H27B . . 107.8 Cl C99 Cl 2 . 111.87(14) Cl C99 H99 2 . 109.2 Cl C99 H99 . . 109.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C11 . 1.3879(17) ? O1 C1 . 1.4028(18) ? O2 C21 . 1.3884(18) ? O2 C1 . 1.4181(19) ? C1 H1A . 0.9900 ? C1 H1B . 0.9900 ? C11 C12 . 1.393(2) ? C11 C16 . 1.402(2) ? C12 C13 . 1.391(2) ? C12 C27 2 1.519(2) ? C13 C14 . 1.391(2) ? C13 H13 . 0.9500 ? C14 C15 . 1.384(2) ? C14 H14 . 0.9500 ? C15 C16 . 1.396(2) ? C15 H15 . 0.9500 ? C16 C17 . 1.524(2) ? C17 C22 . 1.518(2) ? C17 H17A . 0.9900 ? C17 H17B . 0.9900 ? C21 C22 . 1.396(2) ? C21 C26 . 1.397(2) ? C22 C23 . 1.390(2) ? C23 C24 . 1.384(2) ? C23 H23 . 0.9500 ? C24 C25 . 1.380(2) ? C24 H24 . 0.9500 ? C25 C26 . 1.395(2) ? C25 H25 . 0.9500 ? C26 C27 . 1.518(2) ? C27 H27A . 0.9900 ? C27 H27B . 0.9900 ? C99 Cl 2 1.7539(15) ? C99 Cl . 1.7539(15) ? C99 H99 . 0.9900 ? 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 C27 H27A Cl 3 0.99 2.83 3.8128(17) 170 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_4 _geom_torsion _geom_torsion_publ_flag C11 O1 C1 O2 . . 111.24(14) y C21 O2 C1 O1 . . -29.61(18) y C1 O1 C11 C12 . . 136.93(13) y C1 O1 C11 C16 . . -46.25(19) ? O1 C11 C12 C13 . . 177.96(12) ? C16 C11 C12 C13 . . 1.1(2) ? O1 C11 C12 C27 . 2 -1.83(19) ? C16 C11 C12 C27 . 2 -178.65(13) y C11 C12 C13 C14 . . -0.4(2) ? C27 C12 C13 C14 2 . 179.37(14) ? C12 C13 C14 C15 . . -0.3(2) ? C13 C14 C15 C16 . . 0.3(2) ? C14 C15 C16 C11 . . 0.4(2) ? C14 C15 C16 C17 . . -176.86(13) ? O1 C11 C16 C15 . . -177.67(12) ? C12 C11 C16 C15 . . -1.1(2) ? O1 C11 C16 C17 . . -0.6(2) ? C12 C11 C16 C17 . . 175.99(13) ? C15 C16 C17 C22 . . 125.23(15) ? C11 C16 C17 C22 . . -51.79(19) ? C1 O2 C21 C22 . . -51.89(19) ? C1 O2 C21 C26 . . 132.11(14) y O2 C21 C22 C23 . . -173.03(12) ? C26 C21 C22 C23 . . 2.8(2) ? O2 C21 C22 C17 . . 6.6(2) ? C26 C21 C22 C17 . . -177.60(13) ? C16 C17 C22 C23 . . -96.46(16) ? C16 C17 C22 C21 . . 83.90(17) ? C21 C22 C23 C24 . . -0.3(2) ? C17 C22 C23 C24 . . -179.97(13) ? C22 C23 C24 C25 . . -1.6(2) ? C23 C24 C25 C26 . . 1.2(2) ? C24 C25 C26 C21 . . 1.1(2) ? C24 C25 C26 C27 . . -179.01(13) ? O2 C21 C26 C25 . . 172.86(12) ? C22 C21 C26 C25 . . -3.1(2) ? O2 C21 C26 C27 . . -7.00(19) y C22 C21 C26 C27 . . 176.99(13) ? C25 C26 C27 C12 . 2 64.44(18) ? C21 C26 C27 C12 . 2 -115.70(15) y