#------------------------------------------------------------------------------ #$Date: 2014-04-01 13:37:31 +0300 (Tue, 01 Apr 2014) $ #$Revision: 108412 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/22/7112236.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_7112236 loop_ _publ_author_name 'Emile R. Engel' 'Vincent J. Smith' 'Charl X. Bezuidenhout' 'Leonard J. Barbour' _publ_section_title ; Uniaxial negative thermal expansion facilitated by weak host-guest interactions ; _journal_name_full Chem.Commun. _journal_page_first 4238 _journal_paper_doi C4CC00849A _journal_volume 50 _journal_year 2014 _chemical_compound_source Sigma _chemical_formula_moiety 'C12 H24 O6, 2(C H3 N1 O2)' _chemical_formula_sum 'C14 H30 N2 O10' _chemical_formula_weight 386.40 _chemical_name_common 210K _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 101.054(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.2363(13) _cell_length_b 8.0254(11) _cell_length_c 13.7678(19) _cell_measurement_reflns_used 4575 _cell_measurement_temperature 210(2) _cell_measurement_theta_max 27.60 _cell_measurement_theta_min 2.45 _cell_volume 1001.6(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_pressure 101.3 _diffrn_ambient_temperature 210(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'INCOATEC quazar mirrior optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 14646 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 28.29 _diffrn_reflns_theta_min 2.45 _diffrn_source 'INCOATEC Mo micro source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_T_max 0.9713 _exptl_absorpt_correction_T_min 0.9578 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'symmetry-related measurements' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cubic prisms' _exptl_crystal_F_000 416 _exptl_crystal_recrystallization_method nitromethane _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.27 _refine_diff_density_max 0.373 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2477 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0472 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.4471P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1224 _refine_ls_wR_factor_ref 0.1311 _reflns_number_gt 1950 _reflns_number_total 2477 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4cc00849a2.cif _[local]_cod_data_source_block C_nitromethane_210K _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 7112236 _iucr_refine_instruction_details ; TITL 210K in P2(1)/n CELL 0.71073 9.2363 8.0254 13.7678 90.000 101.054 90.000 ZERR 2.0000 0.0013 0.0011 0.0019 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 28 60 4 20 MERG 2 FMAP 2 GRID PLAN 20 TEMP -63 SIZE 0.27 0.36 0.4 HTAB BOND$H CONF L.S. 20 ACTA 52 WGHT 0.048300 0.447100 FVAR 0.21382 O1 4 0.263190 0.399956 0.344905 11.00000 0.03754 0.04347 = 0.04152 0.00019 0.00069 0.00654 O2 4 0.521077 0.564571 0.303906 11.00000 0.04800 0.04530 = 0.03764 -0.00610 0.01315 0.00076 O3 4 0.783460 0.581886 0.456400 11.00000 0.04574 0.03989 = 0.04929 0.00010 0.01143 -0.00596 O4 4 0.227049 0.866946 0.507266 11.00000 0.05204 0.08957 = 0.10890 0.00692 0.00674 0.02697 O5 4 0.413513 0.910181 0.621670 11.00000 0.09624 0.09676 = 0.08217 -0.04599 0.00021 0.02100 N1 3 0.355124 0.842399 0.545593 11.00000 0.04616 0.04015 = 0.04719 0.00401 0.01131 0.00789 C1 1 0.122858 0.414015 0.370920 11.00000 0.03196 0.05558 = 0.05997 -0.01142 -0.00275 0.00295 AFIX 23 H1A 2 0.047661 0.363818 0.319304 11.00000 -1.20000 H1B 2 0.098009 0.531769 0.377082 11.00000 -1.20000 AFIX 0 C2 1 0.271320 0.481607 0.254716 11.00000 0.05537 0.04353 = 0.03901 -0.00004 -0.00889 0.00413 AFIX 23 H2A 2 0.246420 0.599716 0.259126 11.00000 -1.20000 H2B 2 0.200661 0.431557 0.200338 11.00000 -1.20000 AFIX 0 C3 1 0.423947 0.464765 0.235308 11.00000 0.06735 0.04446 = 0.02956 -0.00341 0.00693 0.00108 AFIX 23 H3A 2 0.455072 0.347927 0.242187 11.00000 -1.20000 H3B 2 0.426464 0.500713 0.167626 11.00000 -1.20000 AFIX 0 C4 1 0.667722 0.558851 0.287656 11.00000 0.05686 0.05361 = 0.04319 0.00413 0.02565 0.00872 AFIX 23 H4A 2 0.671086 0.600780 0.221273 11.00000 -1.20000 H4B 2 0.703134 0.443475 0.292127 11.00000 -1.20000 AFIX 0 C5 1 0.764117 0.663122 0.363504 11.00000 0.04482 0.04522 = 0.05847 0.00903 0.02427 0.00140 AFIX 23 H5A 2 0.860094 0.679840 0.344569 11.00000 -1.20000 H5B 2 0.718625 0.772523 0.367791 11.00000 -1.20000 AFIX 0 C6 1 0.874175 0.673040 0.533122 11.00000 0.03754 0.05101 = 0.06635 -0.01044 0.01253 -0.00969 AFIX 23 H6A 2 0.835169 0.786075 0.536209 11.00000 -1.20000 H6B 2 0.974429 0.681300 0.519820 11.00000 -1.20000 AFIX 0 C7 1 0.439867 0.721571 0.499347 11.00000 0.04730 0.04022 = 0.04970 -0.00222 0.01123 0.00869 AFIX 137 H7A 2 0.382835 0.620124 0.484469 11.00000 -1.50000 H7B 2 0.531595 0.696513 0.544356 11.00000 -1.50000 H7C 2 0.461238 0.768133 0.438621 11.00000 -1.50000 HKLF 4 REM 210K in P2(1)/n REM R1 = 0.0472 for 1950 Fo > 4sig(Fo) and 0.0602 for all 2477 data REM 119 parameters refined using 0 restraints END WGHT 0.0483 0.4471 REM Highest difference peak 0.373, deepest hole -0.277, 1-sigma level 0.038 Q1 1 0.2984 0.9491 0.4947 11.00000 0.05 0.37 Q2 1 0.4424 0.9562 0.5625 11.00000 0.05 0.27 Q3 1 0.3430 0.8247 0.6141 11.00000 0.05 0.23 Q4 1 0.2429 0.8152 0.5661 11.00000 0.05 0.22 Q5 1 0.3570 0.4760 0.2574 11.00000 0.05 0.18 Q6 1 0.3796 0.6851 0.4291 11.00000 0.05 0.17 Q7 1 0.2094 0.8040 0.4530 11.00000 0.05 0.14 Q8 1 0.5778 0.5836 0.2824 11.00000 0.05 0.14 Q9 1 0.4594 0.6233 0.5455 11.00000 0.05 0.12 Q10 1 0.3718 0.5799 0.1621 11.00000 0.05 0.12 Q11 1 0.8621 0.6528 0.5838 11.00000 0.05 0.12 Q12 1 1.0326 0.5106 0.5604 11.00000 0.05 0.11 Q13 1 0.7608 0.5076 0.4716 11.00000 0.05 0.11 Q14 1 0.5340 0.7767 0.5198 11.00000 0.05 0.11 Q15 1 0.7115 0.6187 0.3252 11.00000 0.05 0.11 Q16 1 0.3924 0.7599 0.5201 11.00000 0.05 0.11 Q17 1 0.4980 0.6053 0.3503 11.00000 0.05 0.11 Q18 1 0.7206 0.6042 0.5084 11.00000 0.05 0.11 Q19 1 0.2232 0.3741 0.3762 11.00000 0.05 0.10 Q20 1 0.9006 0.6781 0.3954 11.00000 0.05 0.10 ; loop_ _symmetry_equiv_pos_as_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_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O1 O 0.26319(12) 0.39996(14) 0.34491(8) 0.0418(3) Uani 1 1 d . O2 O 0.52108(13) 0.56457(14) 0.30391(8) 0.0430(3) Uani 1 1 d . O3 O 0.78346(13) 0.58189(14) 0.45640(9) 0.0447(3) Uani 1 1 d . O4 O 0.22705(17) 0.8669(2) 0.50727(15) 0.0847(5) Uani 1 1 d . O5 O 0.4135(2) 0.9102(3) 0.62167(14) 0.0940(6) Uani 1 1 d . N1 N 0.35512(16) 0.84240(18) 0.54559(11) 0.0442(3) Uani 1 1 d . C1 C 0.12286(18) 0.4140(2) 0.37092(14) 0.0507(4) Uani 1 1 d . H1A H 0.0477 0.3638 0.3193 0.061 Uiso 1 1 calc R H1B H 0.0980 0.5318 0.3771 0.061 Uiso 1 1 calc R C2 C 0.2713(2) 0.4816(2) 0.25472(13) 0.0484(4) Uani 1 1 d . H2A H 0.2464 0.5997 0.2591 0.058 Uiso 1 1 calc R H2B H 0.2007 0.4316 0.2003 0.058 Uiso 1 1 calc R C3 C 0.4239(2) 0.4648(2) 0.23531(12) 0.0474(4) Uani 1 1 d . H3A H 0.4551 0.3479 0.2422 0.057 Uiso 1 1 calc R H3B H 0.4265 0.5007 0.1676 0.057 Uiso 1 1 calc R C4 C 0.6677(2) 0.5589(2) 0.28766(13) 0.0491(4) Uani 1 1 d . H4A H 0.6711 0.6008 0.2213 0.059 Uiso 1 1 calc R H4B H 0.7031 0.4435 0.2921 0.059 Uiso 1 1 calc R C5 C 0.76412(19) 0.6631(2) 0.36350(13) 0.0476(4) Uani 1 1 d . H5A H 0.8601 0.6798 0.3446 0.057 Uiso 1 1 calc R H5B H 0.7186 0.7725 0.3678 0.057 Uiso 1 1 calc R C6 C 0.87417(19) 0.6730(2) 0.53312(14) 0.0513(4) Uani 1 1 d . H6A H 0.8352 0.7861 0.5362 0.062 Uiso 1 1 calc R H6B H 0.9744 0.6813 0.5198 0.062 Uiso 1 1 calc R C7 C 0.43987(19) 0.7216(2) 0.49935(13) 0.0455(4) Uani 1 1 d . H7A H 0.3828 0.6201 0.4845 0.068 Uiso 1 1 calc R H7B H 0.5316 0.6965 0.5444 0.068 Uiso 1 1 calc R H7C H 0.4612 0.7681 0.4386 0.068 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0375(6) 0.0435(6) 0.0415(6) 0.0002(5) 0.0007(5) 0.0065(5) O2 0.0480(7) 0.0453(6) 0.0376(6) -0.0061(5) 0.0131(5) 0.0008(5) O3 0.0457(6) 0.0399(6) 0.0493(7) 0.0001(5) 0.0114(5) -0.0060(5) O4 0.0520(9) 0.0896(12) 0.1089(14) 0.0069(10) 0.0067(8) 0.0270(8) O5 0.0962(13) 0.0968(13) 0.0822(12) -0.0460(10) 0.0002(10) 0.0210(11) N1 0.0462(8) 0.0401(7) 0.0472(8) 0.0040(6) 0.0113(6) 0.0079(6) C1 0.0320(8) 0.0556(10) 0.0600(11) -0.0114(9) -0.0027(7) 0.0030(7) C2 0.0554(10) 0.0435(9) 0.0390(8) 0.0000(7) -0.0089(7) 0.0041(8) C3 0.0673(11) 0.0445(9) 0.0296(7) -0.0034(6) 0.0069(7) 0.0011(8) C4 0.0569(10) 0.0536(10) 0.0432(9) 0.0041(8) 0.0256(8) 0.0087(8) C5 0.0448(9) 0.0452(9) 0.0585(10) 0.0090(8) 0.0243(8) 0.0014(7) C6 0.0375(8) 0.0510(10) 0.0663(12) -0.0104(9) 0.0125(8) -0.0097(7) C7 0.0473(9) 0.0402(8) 0.0497(9) -0.0022(7) 0.0112(7) 0.0087(7) 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' N N 0.0061 0.0033 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 C1 O1 C2 112.94(13) . . C4 O2 C3 112.25(13) . . C5 O3 C6 112.91(13) . . O5 N1 O4 122.52(17) . . O5 N1 C7 119.10(16) . . O4 N1 C7 118.35(16) . . O1 C1 C6 108.98(14) . 3_666 O1 C1 H1A 109.9 . . C6 C1 H1A 109.9 3_666 . O1 C1 H1B 109.9 . . C6 C1 H1B 109.9 3_666 . H1A C1 H1B 108.3 . . O1 C2 C3 109.00(13) . . O1 C2 H2A 109.9 . . C3 C2 H2A 109.9 . . O1 C2 H2B 109.9 . . C3 C2 H2B 109.9 . . H2A C2 H2B 108.3 . . O2 C3 C2 109.18(13) . . O2 C3 H3A 109.8 . . C2 C3 H3A 109.8 . . O2 C3 H3B 109.8 . . C2 C3 H3B 109.8 . . H3A C3 H3B 108.3 . . O2 C4 C5 109.38(13) . . O2 C4 H4A 109.8 . . C5 C4 H4A 109.8 . . O2 C4 H4B 109.8 . . C5 C4 H4B 109.8 . . H4A C4 H4B 108.2 . . O3 C5 C4 109.20(14) . . O3 C5 H5A 109.8 . . C4 C5 H5A 109.8 . . O3 C5 H5B 109.8 . . C4 C5 H5B 109.8 . . H5A C5 H5B 108.3 . . O3 C6 C1 109.03(14) . 3_666 O3 C6 H6A 109.9 . . C1 C6 H6A 109.9 3_666 . O3 C6 H6B 109.9 . . C1 C6 H6B 109.9 3_666 . H6A C6 H6B 108.3 . . N1 C7 H7A 109.5 . . N1 C7 H7B 109.5 . . H7A C7 H7B 109.5 . . N1 C7 H7C 109.5 . . H7A C7 H7C 109.5 . . H7B C7 H7C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 C1 1.414(2) . O1 C2 1.419(2) . O2 C4 1.415(2) . O2 C3 1.419(2) . O3 C5 1.416(2) . O3 C6 1.419(2) . O4 N1 1.215(2) . O5 N1 1.211(2) . N1 C7 1.466(2) . C1 C6 1.490(3) 3_666 C1 H1A 0.9800 . C1 H1B 0.9800 . C2 C3 1.490(3) . C2 H2A 0.9800 . C2 H2B 0.9800 . C3 H3A 0.9800 . C3 H3B 0.9800 . C4 C5 1.492(3) . C4 H4A 0.9800 . C4 H4B 0.9800 . C5 H5A 0.9800 . C5 H5B 0.9800 . C6 C1 1.490(3) 3_666 C6 H6A 0.9800 . C6 H6B 0.9800 . C7 H7A 0.9700 . C7 H7B 0.9700 . C7 H7C 0.9700 . 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 _geom_torsion_site_symmetry_4 C2 O1 C1 C6 -179.18(14) 3_666 C1 O1 C2 C3 178.16(14) . C4 O2 C3 C2 -178.05(14) . O1 C2 C3 O2 -70.64(17) . C3 O2 C4 C5 -178.74(14) . C6 O3 C5 C4 -179.99(14) . O2 C4 C5 O3 71.81(17) . C5 O3 C6 C1 174.97(13) 3_666