#------------------------------------------------------------------------------ #$Date: 2014-11-01 08:06:37 +0100 (Sat, 01 Nov 2014) $ #$Revision: 126140 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/22/7112238.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_7112238 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 10.1039/C4CC00849A _journal_volume 50 _journal_year 2014 _chemical_compound_source sigma _chemical_formula_moiety 'C12 H24 O6, 2(C H3 N O2)' _chemical_formula_sum 'C14 H30 N2 O10' _chemical_formula_weight 386.40 _chemical_name_common 260K _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 101.529(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.1488(15) _cell_length_b 8.1812(13) _cell_length_c 13.928(2) _cell_measurement_reflns_used 3351 _cell_measurement_temperature 260(2) _cell_measurement_theta_max 23.29 _cell_measurement_theta_min 2.45 _cell_volume 1021.5(3) _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, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_pressure 101.3 _diffrn_ambient_temperature 260(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.995 _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 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0194 _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 14870 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 28.32 _diffrn_reflns_theta_min 2.46 _diffrn_source 'INCOATEC Mo micro source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_T_max 0.9718 _exptl_absorpt_correction_T_min 0.9586 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'symmetry-related measurements' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.256 _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 0.422 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2530 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.084 _refine_ls_R_factor_all 0.1035 _refine_ls_R_factor_gt 0.0737 _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^)+(0.1118P)^2^+0.5114P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2245 _refine_ls_wR_factor_ref 0.2492 _reflns_number_gt 1647 _reflns_number_total 2530 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4cc00849a2.cif _[local]_cod_data_source_block C_nitromethane_260K _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_hydrogen_treatment' value 'Constr' changed to 'constr' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius ; _cod_original_cell_volume 1021.4(3) _cod_database_code 7112238 _iucr_refine_instruction_details ; TITL 260K in P2(1)/n CELL 0.71073 9.1488 8.1812 13.9278 90.000 101.529 90.000 ZERR 2.0000 0.0015 0.0013 0.0023 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 -13 SIZE 0.27 0.36 0.4 HTAB BOND$H CONF L.S. 20 ACTA 52 WGHT 0.111800 0.511400 FVAR 0.21607 O1 4 0.261177 0.399738 0.346540 11.00000 0.05792 0.06087 = 0.06440 -0.00314 0.00044 0.00985 O2 4 0.517624 0.567556 0.304931 11.00000 0.07894 0.06236 = 0.05418 -0.00552 0.02216 0.00526 O3 4 0.782399 0.588058 0.456223 11.00000 0.06382 0.05761 = 0.07943 -0.00002 0.02281 -0.00641 O4 4 0.224279 0.864693 0.504906 11.00000 0.07517 0.13354 = 0.18481 0.01571 0.01546 0.03869 O5 4 0.406440 0.901788 0.620850 11.00000 0.16312 0.15870 = 0.11823 -0.07126 -0.00524 0.05504 N1 3 0.353148 0.839880 0.544512 11.00000 0.07263 0.05983 = 0.06727 0.00324 0.01569 0.01554 C1 1 0.120958 0.409138 0.372656 11.00000 0.04718 0.08128 = 0.09666 -0.02162 -0.00620 0.00326 AFIX 23 H1A 2 0.046075 0.358813 0.322159 11.00000 -1.20000 H1B 2 0.093746 0.522726 0.378668 11.00000 -1.20000 AFIX 0 C2 1 0.267072 0.480922 0.257158 11.00000 0.08920 0.06391 = 0.05991 -0.00222 -0.01751 0.00870 AFIX 23 H2A 2 0.240524 0.595044 0.261714 11.00000 -1.20000 H2B 2 0.196254 0.431556 0.203906 11.00000 -1.20000 AFIX 0 C3 1 0.419894 0.468019 0.237321 11.00000 0.11017 0.06582 = 0.04289 -0.00364 0.01127 0.00576 AFIX 23 H3A 2 0.453097 0.355236 0.243882 11.00000 -1.20000 H3B 2 0.420247 0.503472 0.170909 11.00000 -1.20000 AFIX 0 C4 1 0.665280 0.565036 0.289504 11.00000 0.09230 0.07577 = 0.06412 0.00838 0.04298 0.01704 AFIX 23 H4A 2 0.667570 0.606587 0.224594 11.00000 -1.20000 H4B 2 0.702068 0.453541 0.293560 11.00000 -1.20000 AFIX 0 C5 1 0.762130 0.667077 0.364365 11.00000 0.07069 0.06340 = 0.09442 0.01601 0.04450 0.00485 AFIX 23 H5A 2 0.857999 0.683598 0.346146 11.00000 -1.20000 H5B 2 0.716331 0.773166 0.368261 11.00000 -1.20000 AFIX 0 C6 1 0.873386 0.676230 0.532738 11.00000 0.05275 0.07395 = 0.11109 -0.01790 0.02369 -0.01629 AFIX 23 H6A 2 0.833490 0.785451 0.536162 11.00000 -1.20000 H6B 2 0.973339 0.685903 0.519792 11.00000 -1.20000 AFIX 0 C7 1 0.435569 0.717254 0.500916 11.00000 0.06868 0.05604 = 0.07117 -0.00413 0.01758 0.01339 AFIX 137 H7A 2 0.453225 0.756813 0.439345 11.00000 -1.50000 H7B 2 0.378482 0.618099 0.490490 11.00000 -1.50000 H7C 2 0.529257 0.696129 0.544215 11.00000 -1.50000 HKLF 4 REM 260K in P2(1)/n REM R1 = 0.0737 for 1647 Fo > 4sig(Fo) and 0.1035 for all 2530 data REM 119 parameters refined using 0 restraints END WGHT 0.1118 0.5114 REM Highest difference peak 0.422, deepest hole -0.361, 1-sigma level 0.049 Q1 1 0.4561 0.9478 0.5560 11.00000 0.05 0.42 Q2 1 0.3278 0.9650 0.4973 11.00000 0.05 0.41 Q3 1 0.2866 0.8297 0.5991 11.00000 0.05 0.39 Q4 1 0.4036 0.9161 0.6440 11.00000 0.05 0.26 Q5 1 0.4900 0.7726 0.4984 11.00000 0.05 0.17 Q6 1 0.5580 0.5755 0.2664 11.00000 0.05 0.16 Q7 1 0.7125 0.5980 0.5007 11.00000 0.05 0.14 Q8 1 0.3565 0.6917 0.4339 11.00000 0.05 0.14 Q9 1 0.4326 0.5811 0.2962 11.00000 0.05 0.14 Q10 1 0.7419 0.5270 0.4668 11.00000 0.05 0.13 Q11 1 0.2044 0.3321 0.4003 11.00000 0.05 0.12 Q12 1 0.2953 0.7578 0.5166 11.00000 0.05 0.12 Q13 1 0.3022 0.4489 0.3554 11.00000 0.05 0.12 Q14 1 0.8434 0.6898 0.5759 11.00000 0.05 0.12 Q15 1 0.6957 0.4981 0.2265 11.00000 0.05 0.12 Q16 1 0.5109 0.5131 0.3020 11.00000 0.05 0.11 Q17 1 0.2293 0.7819 0.4436 11.00000 0.05 0.11 Q18 1 0.4623 0.6157 0.5668 11.00000 0.05 0.11 Q19 1 0.3527 0.4977 0.2528 11.00000 0.05 0.11 Q20 1 0.2874 0.3840 0.3221 11.00000 0.05 0.11 ; 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 0.2612(2) 0.3997(2) 0.34654(14) 0.0627(6) Uani 1 1 d . O2 O 0.5176(2) 0.5676(2) 0.30493(13) 0.0639(6) Uani 1 1 d . O3 O 0.7824(2) 0.5881(2) 0.45622(15) 0.0658(6) Uani 1 1 d . O4 O 0.2243(3) 0.8647(4) 0.5049(3) 0.1326(13) Uani 1 1 d . O5 O 0.4064(5) 0.9018(5) 0.6209(3) 0.1513(16) Uani 1 1 d . N1 N 0.3531(3) 0.8399(3) 0.54451(19) 0.0663(7) Uani 1 1 d . C1 C 0.1210(3) 0.4091(4) 0.3727(3) 0.0779(10) Uani 1 1 d . H1A H 0.0461 0.3588 0.3222 0.093 Uiso 1 1 calc R H1B H 0.0937 0.5227 0.3787 0.093 Uiso 1 1 calc R C2 C 0.2671(4) 0.4809(4) 0.2572(2) 0.0755(9) Uani 1 1 d . H2A H 0.2405 0.5950 0.2617 0.091 Uiso 1 1 calc R H2B H 0.1963 0.4316 0.2039 0.091 Uiso 1 1 calc R C3 C 0.4199(4) 0.4680(4) 0.2373(2) 0.0735(9) Uani 1 1 d . H3A H 0.4531 0.3552 0.2439 0.088 Uiso 1 1 calc R H3B H 0.4202 0.5035 0.1709 0.088 Uiso 1 1 calc R C4 C 0.6653(4) 0.5650(4) 0.2895(2) 0.0736(9) Uani 1 1 d . H4A H 0.6676 0.6066 0.2246 0.088 Uiso 1 1 calc R H4B H 0.7021 0.4535 0.2936 0.088 Uiso 1 1 calc R C5 C 0.7621(4) 0.6671(4) 0.3644(3) 0.0723(9) Uani 1 1 d . H5A H 0.8580 0.6836 0.3461 0.087 Uiso 1 1 calc R H5B H 0.7163 0.7732 0.3683 0.087 Uiso 1 1 calc R C6 C 0.8734(3) 0.6762(4) 0.5327(3) 0.0782(10) Uani 1 1 d . H6A H 0.8335 0.7855 0.5362 0.094 Uiso 1 1 calc R H6B H 0.9733 0.6859 0.5198 0.094 Uiso 1 1 calc R C7 C 0.4356(3) 0.7173(3) 0.5009(2) 0.0648(7) Uani 1 1 d . H7A H 0.4532 0.7568 0.4393 0.097 Uiso 1 1 calc R H7B H 0.3785 0.6181 0.4905 0.097 Uiso 1 1 calc R H7C H 0.5293 0.6961 0.5442 0.097 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 0.0579(11) 0.0609(11) 0.0644(12) -0.0031(9) 0.0004(8) 0.0098(8) O2 0.0789(13) 0.0624(11) 0.0542(10) -0.0055(8) 0.0222(9) 0.0053(9) O3 0.0638(12) 0.0576(11) 0.0794(13) 0.0000(9) 0.0228(10) -0.0064(9) O4 0.0752(18) 0.134(3) 0.185(3) 0.016(2) 0.0155(19) 0.0387(17) O5 0.163(3) 0.159(3) 0.118(3) -0.071(2) -0.005(2) 0.055(3) N1 0.0726(16) 0.0598(13) 0.0673(15) 0.0032(11) 0.0157(12) 0.0155(11) C1 0.0472(15) 0.081(2) 0.097(2) -0.0216(18) -0.0062(14) 0.0033(14) C2 0.089(2) 0.0639(17) 0.0599(17) -0.0022(13) -0.0175(15) 0.0087(15) C3 0.110(3) 0.0658(17) 0.0429(13) -0.0036(12) 0.0113(15) 0.0058(16) C4 0.092(2) 0.0758(19) 0.0641(17) 0.0084(14) 0.0430(16) 0.0170(16) C5 0.0707(18) 0.0634(16) 0.094(2) 0.0160(16) 0.0445(17) 0.0048(14) C6 0.0528(16) 0.0739(19) 0.111(3) -0.0179(18) 0.0237(16) -0.0163(14) C7 0.0687(17) 0.0560(15) 0.0712(17) -0.0041(13) 0.0176(14) 0.0134(12) 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 113.4(2) . . C4 O2 C3 112.7(2) . . C5 O3 C6 113.6(2) . . O5 N1 O4 121.4(3) . . O5 N1 C7 120.7(3) . . O4 N1 C7 117.5(3) . . O1 C1 C6 109.5(2) . 3_666 O1 C1 H1A 109.8 . . C6 C1 H1A 109.8 3_666 . O1 C1 H1B 109.8 . . C6 C1 H1B 109.8 3_666 . H1A C1 H1B 108.2 . . O1 C2 C3 109.4(2) . . O1 C2 H2A 109.8 . . C3 C2 H2A 109.8 . . O1 C2 H2B 109.8 . . C3 C2 H2B 109.8 . . H2A C2 H2B 108.2 . . O2 C3 C2 109.2(2) . . 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 109.9(2) . . O2 C4 H4A 109.7 . . C5 C4 H4A 109.7 . . O2 C4 H4B 109.7 . . C5 C4 H4B 109.7 . . H4A C4 H4B 108.2 . . O3 C5 C4 109.3(2) . . 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 109.9(2) . 3_666 O3 C6 H6A 109.7 . . C1 C6 H6A 109.7 3_666 . O3 C6 H6B 109.7 . . C1 C6 H6B 109.7 3_666 . H6A C6 H6B 108.2 . . 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 1.404(4) . O1 C2 1.421(4) . O2 C4 1.410(4) . O2 C3 1.419(4) . O3 C5 1.412(4) . O3 C6 1.412(4) . O4 N1 1.215(4) . O5 N1 1.191(4) . N1 C7 1.458(3) . C1 C6 1.483(5) 3_666 C1 H1A 0.9700 . C1 H1B 0.9700 . C2 C3 1.482(5) . C2 H2A 0.9700 . C2 H2B 0.9700 . C3 H3A 0.9700 . C3 H3B 0.9700 . C4 C5 1.483(5) . C4 H4A 0.9700 . C4 H4B 0.9700 . C5 H5A 0.9700 . C5 H5B 0.9700 . C6 C1 1.483(5) 3_666 C6 H6A 0.9700 . C6 H6B 0.9700 . C7 H7A 0.9600 . C7 H7B 0.9600 . C7 H7C 0.9600 . 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 -179.0(2) 3_666 C1 O1 C2 C3 178.5(2) . C4 O2 C3 C2 -178.6(2) . O1 C2 C3 O2 -70.8(3) . C3 O2 C4 C5 -178.2(2) . C6 O3 C5 C4 -179.9(2) . O2 C4 C5 O3 71.1(3) . C5 O3 C6 C1 175.7(2) 3_666