#------------------------------------------------------------------------------ #$Date: 2014-11-01 08:06:37 +0100 (Sat, 01 Nov 2014) $ #$Revision: 126140 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/22/7112234.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_7112234 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 150K _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 100.818(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.2849(12) _cell_length_b 7.9079(10) _cell_length_c 13.6739(18) _cell_measurement_reflns_used 5739 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29.28 _cell_measurement_theta_min 2.45 _cell_volume 986.2(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 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.938 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'INCOATEC quazar mirrior optics' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0167 _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 14663 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.76 _diffrn_reflns_theta_min 2.45 _diffrn_source 'INCOATEC Mo micro source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 0.9708 _exptl_absorpt_correction_T_min 0.9572 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'symmetry-related measurements' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.301 _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 0.280 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2626 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0377 _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^)+(0.0384P)^2^+0.3486P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0965 _refine_ls_wR_factor_ref 0.1017 _reflns_number_gt 2189 _reflns_number_total 2626 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4cc00849a2.cif _[local]_cod_data_source_block C_nitromethane_150K _[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_database_code 7112234 _iucr_refine_instruction_details ; TITL 150K in P2(1)/n CELL 0.71073 9.2849 7.9079 13.6739 90.000 100.818 90.000 ZERR 2.0000 0.0012 0.0010 0.0018 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 OMIT 2 3 11 FMAP 2 GRID PLAN 20 TEMP -123 SIZE 0.27 0.36 0.4 CONF HTAB BOND$H L.S. 20 ACTA 52 WGHT 0.038400 0.348600 FVAR 0.20579 O1 4 0.263788 0.399709 0.344115 11.00000 0.02429 0.02948 = 0.02657 0.00103 0.00127 0.00424 O2 4 0.522793 0.562756 0.303420 11.00000 0.02916 0.03143 = 0.02512 -0.00520 0.00752 -0.00084 O3 4 0.784513 0.578430 0.456425 11.00000 0.03088 0.02679 = 0.03036 0.00066 0.00504 -0.00419 O4 4 0.228332 0.867982 0.508457 11.00000 0.03217 0.05702 = 0.06547 0.00393 0.00317 0.01693 O5 4 0.416043 0.911805 0.623565 11.00000 0.05925 0.05870 = 0.04943 -0.02566 0.00050 0.01032 N1 3 0.356083 0.843124 0.546717 11.00000 0.03046 0.02644 = 0.03116 0.00337 0.00723 0.00449 C1 1 0.123258 0.415982 0.369536 11.00000 0.02140 0.03656 = 0.03664 -0.00565 -0.00106 0.00259 AFIX 23 H1A 2 0.048057 0.364543 0.317041 11.00000 -1.20000 H1B 2 0.098953 0.537032 0.375289 11.00000 -1.20000 AFIX 0 C2 1 0.273222 0.481609 0.253101 11.00000 0.03395 0.02884 = 0.02562 0.00178 -0.00424 0.00161 AFIX 23 H2A 2 0.249103 0.603041 0.257190 11.00000 -1.20000 H2B 2 0.202414 0.430462 0.197852 11.00000 -1.20000 AFIX 0 C3 1 0.426067 0.462178 0.234128 11.00000 0.04029 0.02986 = 0.01988 -0.00239 0.00370 -0.00048 AFIX 23 H3A 2 0.456121 0.342026 0.241379 11.00000 -1.20000 H3B 2 0.429985 0.498498 0.165390 11.00000 -1.20000 AFIX 0 C4 1 0.668883 0.555533 0.286579 11.00000 0.03433 0.03605 = 0.02705 0.00118 0.01407 0.00400 AFIX 23 H4A 2 0.672535 0.598123 0.219005 11.00000 -1.20000 H4B 2 0.703752 0.436977 0.291172 11.00000 -1.20000 AFIX 0 C5 1 0.765605 0.661454 0.362929 11.00000 0.02839 0.03071 = 0.03464 0.00519 0.01310 -0.00014 AFIX 23 H5A 2 0.862006 0.678125 0.343355 11.00000 -1.20000 H5B 2 0.720343 0.773816 0.367553 11.00000 -1.20000 AFIX 0 C6 1 0.875295 0.671794 0.533084 11.00000 0.02481 0.03356 = 0.04040 -0.00597 0.00588 -0.00617 AFIX 23 H6A 2 0.836877 0.788161 0.535698 11.00000 -1.20000 H6B 2 0.976168 0.678797 0.519498 11.00000 -1.20000 AFIX 0 C7 1 0.441871 0.723349 0.497719 11.00000 0.03033 0.02739 = 0.03258 -0.00165 0.00626 0.00568 AFIX 137 H7A 2 0.383774 0.621070 0.478637 11.00000 -1.50000 H7B 2 0.532280 0.693282 0.543857 11.00000 -1.50000 H7C 2 0.466489 0.776210 0.438148 11.00000 -1.50000 HKLF 4 REM 150K in P2(1)/n REM R1 = 0.0377 for 2189 Fo > 4sig(Fo) and 0.0465 for all 2626 data REM 119 parameters refined using 0 restraints END WGHT 0.0386 0.3458 REM Highest difference peak 0.280, deepest hole -0.232, 1-sigma level 0.038 Q1 1 0.2855 0.9336 0.4962 11.00000 0.05 0.28 Q2 1 0.3510 0.4805 0.2491 11.00000 0.05 0.27 Q3 1 0.7204 0.6092 0.3269 11.00000 0.05 0.24 Q4 1 0.1427 0.3569 0.4153 11.00000 0.05 0.23 Q5 1 0.4540 0.9394 0.5780 11.00000 0.05 0.21 Q6 1 0.3977 0.7729 0.5196 11.00000 0.05 0.19 Q7 1 0.3812 0.6871 0.4385 11.00000 0.05 0.17 Q8 1 0.2431 0.8226 0.5549 11.00000 0.05 0.17 Q9 1 0.2058 0.8144 0.4639 11.00000 0.05 0.16 Q10 1 0.4155 0.9225 0.6465 11.00000 0.05 0.15 Q11 1 0.5857 0.5733 0.2813 11.00000 0.05 0.15 Q12 1 0.3633 0.8352 0.6139 11.00000 0.05 0.15 Q13 1 0.2713 0.4266 0.3029 11.00000 0.05 0.15 Q14 1 0.1985 0.3974 0.3551 11.00000 0.05 0.14 Q15 1 0.7228 0.6110 0.4977 11.00000 0.05 0.13 Q16 1 0.4797 0.5860 0.3457 11.00000 0.05 0.12 Q17 1 0.4716 0.4423 0.1766 11.00000 0.05 0.12 Q18 1 0.4820 0.5068 0.2624 11.00000 0.05 0.12 Q19 1 0.5235 0.7666 0.4988 11.00000 0.05 0.12 Q20 1 0.4965 0.6744 0.3023 11.00000 0.05 0.12 ; 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 0.26379(9) 0.39971(10) 0.34412(6) 0.02723(19) Uani 1 1 d . O2 O 0.52279(9) 0.56276(11) 0.30342(6) 0.02825(19) Uani 1 1 d . O3 O 0.78451(9) 0.57843(10) 0.45643(6) 0.0294(2) Uani 1 1 d . O4 O 0.22833(11) 0.86798(15) 0.50846(9) 0.0523(3) Uani 1 1 d . O5 O 0.41604(14) 0.91180(16) 0.62357(9) 0.0570(3) Uani 1 1 d . N1 N 0.35608(11) 0.84312(13) 0.54672(8) 0.0292(2) Uani 1 1 d . C1 C 0.12326(13) 0.41598(17) 0.36954(10) 0.0324(3) Uani 1 1 d . H1A H 0.0481 0.3645 0.3170 0.039 Uiso 1 1 calc R H1B H 0.0990 0.5370 0.3753 0.039 Uiso 1 1 calc R C2 C 0.27322(14) 0.48161(16) 0.25310(9) 0.0307(3) Uani 1 1 d . H2A H 0.2491 0.6030 0.2572 0.037 Uiso 1 1 calc R H2B H 0.2024 0.4305 0.1979 0.037 Uiso 1 1 calc R C3 C 0.42607(14) 0.46218(16) 0.23413(8) 0.0303(3) Uani 1 1 d . H3A H 0.4561 0.3420 0.2414 0.036 Uiso 1 1 calc R H3B H 0.4300 0.4985 0.1654 0.036 Uiso 1 1 calc R C4 C 0.66888(14) 0.55553(17) 0.28658(9) 0.0314(3) Uani 1 1 d . H4A H 0.6725 0.5981 0.2190 0.038 Uiso 1 1 calc R H4B H 0.7038 0.4370 0.2912 0.038 Uiso 1 1 calc R C5 C 0.76561(13) 0.66145(16) 0.36293(9) 0.0303(3) Uani 1 1 d . H5A H 0.8620 0.6781 0.3434 0.036 Uiso 1 1 calc R H5B H 0.7203 0.7738 0.3676 0.036 Uiso 1 1 calc R C6 C 0.87530(13) 0.67179(16) 0.53308(10) 0.0330(3) Uani 1 1 d . H6A H 0.8369 0.7882 0.5357 0.040 Uiso 1 1 calc R H6B H 0.9762 0.6788 0.5195 0.040 Uiso 1 1 calc R C7 C 0.44187(13) 0.72335(15) 0.49772(9) 0.0301(3) Uani 1 1 d . H7A H 0.3838 0.6211 0.4786 0.045 Uiso 1 1 calc R H7B H 0.5323 0.6933 0.5439 0.045 Uiso 1 1 calc R H7C H 0.4665 0.7762 0.4381 0.045 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 0.0243(4) 0.0295(4) 0.0266(4) 0.0010(3) 0.0013(3) 0.0042(3) O2 0.0292(4) 0.0314(4) 0.0251(4) -0.0052(3) 0.0075(3) -0.0008(3) O3 0.0309(4) 0.0268(4) 0.0304(4) 0.0007(3) 0.0050(3) -0.0042(3) O4 0.0322(5) 0.0570(7) 0.0655(7) 0.0039(6) 0.0032(5) 0.0169(5) O5 0.0592(7) 0.0587(7) 0.0494(6) -0.0257(6) 0.0005(5) 0.0103(6) N1 0.0305(5) 0.0264(5) 0.0312(5) 0.0034(4) 0.0072(4) 0.0045(4) C1 0.0214(5) 0.0366(6) 0.0366(7) -0.0057(5) -0.0011(5) 0.0026(5) C2 0.0340(6) 0.0288(6) 0.0256(6) 0.0018(4) -0.0042(5) 0.0016(5) C3 0.0403(7) 0.0299(6) 0.0199(5) -0.0024(4) 0.0037(5) -0.0005(5) C4 0.0343(6) 0.0360(6) 0.0270(6) 0.0012(5) 0.0141(5) 0.0040(5) C5 0.0284(6) 0.0307(6) 0.0346(6) 0.0052(5) 0.0131(5) -0.0001(5) C6 0.0248(6) 0.0336(6) 0.0404(7) -0.0060(5) 0.0059(5) -0.0062(5) C7 0.0303(6) 0.0274(6) 0.0326(6) -0.0016(5) 0.0063(5) 0.0057(5) 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 112.61(9) . . C4 O2 C3 111.91(9) . . C5 O3 C6 112.33(9) . . O4 N1 O5 123.20(11) . . O4 N1 C7 118.22(11) . . O5 N1 C7 118.58(11) . . O1 C1 C6 108.69(10) . 3_666 O1 C1 H1A 110.0 . . C6 C1 H1A 110.0 3_666 . O1 C1 H1B 110.0 . . C6 C1 H1B 110.0 3_666 . H1A C1 H1B 108.3 . . O1 C2 C3 108.74(9) . . 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 109.15(9) . . O2 C3 H3A 109.9 . . C2 C3 H3A 109.9 . . O2 C3 H3B 109.9 . . C2 C3 H3B 109.9 . . H3A C3 H3B 108.3 . . O2 C4 C5 109.30(9) . . O2 C4 H4A 109.8 . . C5 C4 H4A 109.8 . . O2 C4 H4B 109.8 . . C5 C4 H4B 109.8 . . H4A C4 H4B 108.3 . . O3 C5 C4 109.01(10) . . O3 C5 H5A 109.9 . . C4 C5 H5A 109.9 . . O3 C5 H5B 109.9 . . C4 C5 H5B 109.9 . . H5A C5 H5B 108.3 . . O3 C6 C1 108.63(10) . 3_666 O3 C6 H6A 110.0 . . C1 C6 H6A 110.0 3_666 . O3 C6 H6B 110.0 . . C1 C6 H6B 110.0 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 1.4178(14) . O1 C2 1.4202(15) . O2 C4 1.4190(14) . O2 C3 1.4204(14) . O3 C5 1.4185(14) . O3 C6 1.4222(14) . O4 N1 1.2192(14) . O5 N1 1.2205(15) . N1 C7 1.4768(15) . C1 C6 1.4995(19) 3_666 C1 H1A 0.9900 . C1 H1B 0.9900 . C2 C3 1.4977(18) . C2 H2A 0.9900 . C2 H2B 0.9900 . C3 H3A 0.9900 . C3 H3B 0.9900 . C4 C5 1.4987(18) . C4 H4A 0.9900 . C4 H4B 0.9900 . C5 H5A 0.9900 . C5 H5B 0.9900 . C6 C1 1.4995(19) 3_666 C6 H6A 0.9900 . C6 H6B 0.9900 . C7 H7A 0.9800 . C7 H7B 0.9800 . C7 H7C 0.9800 . 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 -179.16(10) 3_666 C1 O1 C2 C3 178.30(9) . C4 O2 C3 C2 -177.46(9) . O1 C2 C3 O2 -70.45(12) . C3 O2 C4 C5 -179.02(10) . C6 O3 C5 C4 -179.91(10) . O2 C4 C5 O3 72.05(12) . C5 O3 C6 C1 174.32(9) 3_666