#------------------------------------------------------------------------------ #$Date: 2014-11-01 07:06:37 +0000 (Sat, 01 Nov 2014) $ #$Revision: 126140 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/22/7112233.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_7112233 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 120K _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 100.755(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.2976(13) _cell_length_b 7.8579(11) _cell_length_c 13.6419(19) _cell_measurement_reflns_used 6385 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 28.34 _cell_measurement_theta_min 2.45 _cell_volume 979.2(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 120(2) _diffrn_measured_fraction_theta_full 0.997 _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_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0151 _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 14239 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 28.35 _diffrn_reflns_theta_min 2.45 _diffrn_source 'INCOATEC Mo micro source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_T_max 0.9706 _exptl_absorpt_correction_T_min 0.9569 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'symmetry-related measurements' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.311 _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 0.311 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2433 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.079 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0333 _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^)+(0.0392P)^2^+0.3119P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0872 _refine_ls_wR_factor_ref 0.0907 _reflns_number_gt 2154 _reflns_number_total 2433 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4cc00849a2.cif _[local]_cod_data_source_block C_nitromethane_120K _[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 7112233 _iucr_refine_instruction_details ; TITL 120K in P2(1)/n CELL 0.71073 9.2976 7.8579 13.6419 90.000 100.755 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 -153 SIZE 0.27 0.36 0.4 BOND$H CONF HTAB OMIT -6 0 6 OMIT -3 3 6 OMIT 0 6 6 OMIT -8 5 7 L.S. 20 ACTA 52 WGHT 0.039200 0.311900 FVAR 0.20649 O1 4 0.263722 0.399435 0.343965 11.00000 0.01967 0.02407 = 0.02118 0.00156 0.00113 0.00338 O2 4 0.523191 0.562231 0.303361 11.00000 0.02244 0.02592 = 0.02069 -0.00439 0.00569 -0.00108 O3 4 0.784917 0.577416 0.456425 11.00000 0.02489 0.02227 = 0.02339 0.00048 0.00359 -0.00377 O4 4 0.228502 0.867992 0.508909 11.00000 0.02539 0.04492 = 0.05159 0.00308 0.00268 0.01307 O5 4 0.416591 0.911512 0.624620 11.00000 0.04662 0.04506 = 0.03774 -0.01813 0.00106 0.00712 N1 3 0.356361 0.842939 0.547165 11.00000 0.02423 0.02104 = 0.02550 0.00328 0.00589 0.00315 C1 1 0.123081 0.416374 0.369072 11.00000 0.01744 0.02965 = 0.02877 -0.00404 -0.00081 0.00206 AFIX 23 H1A 2 0.048179 0.364394 0.316480 11.00000 -1.20000 H1B 2 0.098885 0.538278 0.374562 11.00000 -1.20000 AFIX 0 C2 1 0.273536 0.481482 0.252711 11.00000 0.02678 0.02379 = 0.02022 0.00145 -0.00315 0.00088 AFIX 23 H2A 2 0.249713 0.603786 0.256682 11.00000 -1.20000 H2B 2 0.202855 0.430048 0.197364 11.00000 -1.20000 AFIX 0 C3 1 0.426542 0.461249 0.233790 11.00000 0.03105 0.02408 = 0.01654 -0.00230 0.00277 -0.00095 AFIX 23 H3A 2 0.456204 0.340225 0.241083 11.00000 -1.20000 H3B 2 0.430817 0.497724 0.164930 11.00000 -1.20000 AFIX 0 C4 1 0.668979 0.554610 0.286236 11.00000 0.02646 0.02905 = 0.02168 0.00054 0.01056 0.00289 AFIX 23 H4A 2 0.672569 0.597459 0.218491 11.00000 -1.20000 H4B 2 0.703574 0.435213 0.290754 11.00000 -1.20000 AFIX 0 C5 1 0.765932 0.661010 0.362677 11.00000 0.02302 0.02452 = 0.02763 0.00423 0.00990 -0.00031 AFIX 23 H5A 2 0.862131 0.677561 0.342872 11.00000 -1.20000 H5B 2 0.720964 0.774195 0.367418 11.00000 -1.20000 AFIX 0 C6 1 0.875810 0.671601 0.532983 11.00000 0.02004 0.02705 = 0.03111 -0.00469 0.00448 -0.00472 AFIX 23 H6A 2 0.837743 0.788886 0.535405 11.00000 -1.20000 H6B 2 0.976552 0.678106 0.519293 11.00000 -1.20000 AFIX 0 C7 1 0.442574 0.724046 0.496932 11.00000 0.02461 0.02231 = 0.02671 -0.00156 0.00475 0.00431 AFIX 137 H7A 2 0.384665 0.621475 0.476663 11.00000 -1.50000 H7B 2 0.532648 0.692752 0.543003 11.00000 -1.50000 H7C 2 0.467501 0.779176 0.437864 11.00000 -1.50000 HKLF 4 REM 120K in P2(1)/n REM R1 = 0.0333 for 2154 Fo > 4sig(Fo) and 0.0382 for all 2433 data REM 119 parameters refined using 0 restraints END WGHT 0.0394 0.3116 REM Highest difference peak 0.311, deepest hole -0.215, 1-sigma level 0.036 Q1 1 0.3519 0.4788 0.2482 11.00000 0.05 0.31 Q2 1 0.1265 0.3758 0.4188 11.00000 0.05 0.28 Q3 1 0.7164 0.6100 0.3266 11.00000 0.05 0.24 Q4 1 0.3980 0.7797 0.5194 11.00000 0.05 0.20 Q5 1 0.2844 0.9327 0.4975 11.00000 0.05 0.19 Q6 1 0.2702 0.4311 0.3030 11.00000 0.05 0.17 Q7 1 0.4419 0.9483 0.5763 11.00000 0.05 0.17 Q8 1 0.1967 0.4090 0.3586 11.00000 0.05 0.16 Q9 1 0.5856 0.5694 0.2840 11.00000 0.05 0.16 Q10 1 0.4130 0.6987 0.4400 11.00000 0.05 0.15 Q11 1 0.7755 0.6197 0.4065 11.00000 0.05 0.15 Q12 1 0.4745 0.5086 0.2640 11.00000 0.05 0.14 Q13 1 0.7239 0.6144 0.4933 11.00000 0.05 0.13 Q14 1 0.5013 0.5471 0.3545 11.00000 0.05 0.12 Q15 1 0.6993 0.5151 0.2206 11.00000 0.05 0.12 Q16 1 0.2030 0.8066 0.4587 11.00000 0.05 0.12 Q17 1 0.3627 0.8420 0.6101 11.00000 0.05 0.11 Q18 1 0.3932 0.9545 0.6616 11.00000 0.05 0.11 Q19 1 0.8651 0.5495 0.4401 11.00000 0.05 0.11 Q20 1 0.5317 0.7521 0.5201 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 0.26372(8) 0.39943(9) 0.34396(5) 0.02198(17) Uani 1 1 d . O2 O 0.52319(8) 0.56223(10) 0.30336(5) 0.02280(17) Uani 1 1 d . O3 O 0.78492(8) 0.57742(9) 0.45643(5) 0.02363(17) Uani 1 1 d . O4 O 0.22850(10) 0.86799(13) 0.50891(8) 0.0412(2) Uani 1 1 d . O5 O 0.41659(11) 0.91151(13) 0.62462(7) 0.0440(3) Uani 1 1 d . N1 N 0.35636(10) 0.84294(11) 0.54716(7) 0.02343(19) Uani 1 1 d . C1 C 0.12308(11) 0.41637(15) 0.36907(8) 0.0259(2) Uani 1 1 d . H1A H 0.0482 0.3644 0.3165 0.031 Uiso 1 1 calc R H1B H 0.0989 0.5383 0.3746 0.031 Uiso 1 1 calc R C2 C 0.27354(12) 0.48148(14) 0.25271(8) 0.0246(2) Uani 1 1 d . H2A H 0.2497 0.6038 0.2567 0.029 Uiso 1 1 calc R H2B H 0.2029 0.4300 0.1974 0.029 Uiso 1 1 calc R C3 C 0.42654(12) 0.46125(14) 0.23379(7) 0.0241(2) Uani 1 1 d . H3A H 0.4562 0.3402 0.2411 0.029 Uiso 1 1 calc R H3B H 0.4308 0.4977 0.1649 0.029 Uiso 1 1 calc R C4 C 0.66898(12) 0.55461(14) 0.28624(8) 0.0250(2) Uani 1 1 d . H4A H 0.6726 0.5975 0.2185 0.030 Uiso 1 1 calc R H4B H 0.7036 0.4352 0.2908 0.030 Uiso 1 1 calc R C5 C 0.76593(12) 0.66101(14) 0.36268(8) 0.0244(2) Uani 1 1 d . H5A H 0.8621 0.6776 0.3429 0.029 Uiso 1 1 calc R H5B H 0.7210 0.7742 0.3674 0.029 Uiso 1 1 calc R C6 C 0.87581(11) 0.67160(14) 0.53298(8) 0.0261(2) Uani 1 1 d . H6A H 0.8377 0.7889 0.5354 0.031 Uiso 1 1 calc R H6B H 0.9766 0.6781 0.5193 0.031 Uiso 1 1 calc R C7 C 0.44257(12) 0.72405(14) 0.49693(8) 0.0245(2) Uani 1 1 d . H7A H 0.3847 0.6215 0.4767 0.037 Uiso 1 1 calc R H7B H 0.5326 0.6928 0.5430 0.037 Uiso 1 1 calc R H7C H 0.4675 0.7792 0.4379 0.037 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 0.0197(3) 0.0241(4) 0.0212(4) 0.0016(3) 0.0011(3) 0.0034(3) O2 0.0224(4) 0.0259(4) 0.0207(4) -0.0044(3) 0.0057(3) -0.0011(3) O3 0.0249(4) 0.0223(4) 0.0234(4) 0.0005(3) 0.0036(3) -0.0038(3) O4 0.0254(4) 0.0449(5) 0.0516(6) 0.0031(4) 0.0027(4) 0.0131(4) O5 0.0466(6) 0.0451(5) 0.0377(5) -0.0181(4) 0.0011(4) 0.0071(4) N1 0.0242(4) 0.0210(4) 0.0255(4) 0.0033(3) 0.0059(3) 0.0032(3) C1 0.0174(5) 0.0297(5) 0.0288(5) -0.0040(4) -0.0008(4) 0.0021(4) C2 0.0268(5) 0.0238(5) 0.0202(5) 0.0014(4) -0.0031(4) 0.0009(4) C3 0.0311(5) 0.0241(5) 0.0165(5) -0.0023(4) 0.0028(4) -0.0010(4) C4 0.0265(5) 0.0290(5) 0.0217(5) 0.0005(4) 0.0106(4) 0.0029(4) C5 0.0230(5) 0.0245(5) 0.0276(5) 0.0042(4) 0.0099(4) -0.0003(4) C6 0.0200(5) 0.0271(5) 0.0311(6) -0.0047(4) 0.0045(4) -0.0047(4) C7 0.0246(5) 0.0223(5) 0.0267(5) -0.0016(4) 0.0047(4) 0.0043(4) 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 112.46(8) . . C4 O2 C3 111.77(8) . . C5 O3 C6 112.20(8) . . O4 N1 O5 123.33(10) . . O4 N1 C7 118.15(9) . . O5 N1 C7 118.51(9) . . O1 C1 C6 108.53(8) . 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 108.4 . . O1 C2 C3 108.71(8) . . 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 109.12(8) . . 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 109.31(8) . . 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 109.04(9) . . 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 108.54(9) . 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 108.4 . . 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 1.4185(13) . O1 C2 1.4199(13) . O2 C4 1.4190(12) . O2 C3 1.4211(13) . O3 C5 1.4191(13) . O3 C6 1.4224(13) . O4 N1 1.2218(12) . O5 N1 1.2246(13) . N1 C7 1.4798(13) . C1 C6 1.5027(16) 3_666 C1 H1A 0.9900 . C1 H1B 0.9900 . C2 C3 1.5009(15) . C2 H2A 0.9900 . C2 H2B 0.9900 . C3 H3A 0.9900 . C3 H3B 0.9900 . C4 C5 1.4994(16) . C4 H4A 0.9900 . C4 H4B 0.9900 . C5 H5A 0.9900 . C5 H5B 0.9900 . C6 C1 1.5027(16) 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 -179.09(8) 3_666 C1 O1 C2 C3 178.40(8) . C4 O2 C3 C2 -177.26(8) . O1 C2 C3 O2 -70.35(11) . C3 O2 C4 C5 -179.10(8) . C6 O3 C5 C4 -179.85(8) . O2 C4 C5 O3 72.07(11) . C5 O3 C6 C1 174.08(8) 3_666