#------------------------------------------------------------------------------ #$Date: 2014-11-01 08:06:37 +0100 (Sat, 01 Nov 2014) $ #$Revision: 126140 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/22/7112239.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_7112239 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 273K _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 101.676(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.1231(14) _cell_length_b 8.2311(13) _cell_length_c 13.982(2) _cell_measurement_reflns_used 3101 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 23.01 _cell_measurement_theta_min 2.46 _cell_volume 1028.2(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, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_pressure 101.3 _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.993 _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 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _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 15176 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 28.34 _diffrn_reflns_theta_min 2.46 _diffrn_source 'INCOATEC Mo micro source' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.9720 _exptl_absorpt_correction_T_min 0.9589 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'symmetry-related measurements' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.248 _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 0.465 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 2542 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.1167 _refine_ls_R_factor_gt 0.0823 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1417P)^2^+0.5614P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2599 _refine_ls_wR_factor_ref 0.2926 _reflns_number_gt 1551 _reflns_number_total 2542 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4cc00849a2.cif _[local]_cod_data_source_block C_nitromethane_273K _[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 7112239 _iucr_refine_instruction_details ; TITL 273K in P2(1)/n CELL 0.71073 9.1231 8.2311 13.9822 90.000 101.676 90.000 ZERR 2.0000 0.0014 0.0013 0.0022 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 0 SIZE 0.27 0.36 0.4 HTAB CONF BOND$H L.S. 20 ACTA 52 WGHT 0.141700 0.561400 FVAR 0.21849 0.46785 O1 4 0.260628 0.399652 0.347039 11.00000 0.06431 0.06854 = 0.07000 -0.00410 -0.00025 0.01067 O2 4 0.516260 0.568269 0.305034 11.00000 0.08985 0.06792 = 0.05915 -0.00505 0.02527 0.00724 O3 4 0.781903 0.589645 0.456140 11.00000 0.07171 0.06240 = 0.08946 -0.00117 0.02734 -0.00614 N1 3 0.352510 0.839037 0.544134 11.00000 0.08393 0.06801 = 0.07149 0.00305 0.01687 0.01877 C1 1 0.120059 0.407260 0.373863 11.00000 0.05439 0.08612 = 0.10852 -0.02465 -0.00619 0.00273 AFIX 23 H1A 2 0.044794 0.357059 0.323595 11.00000 -1.20000 H1B 2 0.092082 0.519849 0.380180 11.00000 -1.20000 AFIX 0 C2 1 0.265472 0.480644 0.257809 11.00000 0.10582 0.07018 = 0.06461 -0.00278 -0.02035 0.01110 AFIX 23 H2A 2 0.238312 0.593901 0.262371 11.00000 -1.20000 H2B 2 0.194397 0.431214 0.204796 11.00000 -1.20000 AFIX 0 C3 1 0.419024 0.468720 0.237894 11.00000 0.12649 0.07223 = 0.04622 -0.00290 0.01486 0.00771 AFIX 23 H3A 2 0.453053 0.356875 0.244591 11.00000 -1.20000 H3B 2 0.418883 0.503886 0.171662 11.00000 -1.20000 AFIX 0 C4 1 0.664791 0.566487 0.290126 11.00000 0.10859 0.08447 = 0.07308 0.01239 0.05302 0.02114 AFIX 23 H4A 2 0.667055 0.607572 0.225419 11.00000 -1.20000 H4B 2 0.702154 0.455844 0.294430 11.00000 -1.20000 AFIX 0 C5 1 0.761374 0.668286 0.364527 11.00000 0.07985 0.07048 = 0.10515 0.01803 0.05148 0.00697 AFIX 23 H5A 2 0.857505 0.685095 0.346534 11.00000 -1.20000 H5B 2 0.715014 0.773524 0.368261 11.00000 -1.20000 AFIX 0 C6 1 0.873198 0.677511 0.532838 11.00000 0.05795 0.08237 = 0.12317 -0.01852 0.02723 -0.01641 AFIX 23 H6A 2 0.832534 0.785691 0.536524 11.00000 -1.20000 H6B 2 0.973283 0.688132 0.519904 11.00000 -1.20000 AFIX 0 C7 1 0.434711 0.716110 0.501899 11.00000 0.07400 0.06027 = 0.07588 -0.00352 0.01760 0.01449 AFIX 137 H7A 2 0.451527 0.753440 0.439967 11.00000 -1.50000 H7B 2 0.377727 0.617265 0.492837 11.00000 -1.50000 H7C 2 0.529150 0.696462 0.545009 11.00000 -1.50000 AFIX 0 O4 4 0.223450 0.864007 0.503792 11.00000 0.08369 0.14765 = 0.21601 0.02275 0.02145 0.04212 O5 4 0.403177 0.897847 0.620646 11.00000 0.18700 0.17836 = 0.12735 -0.07409 -0.00371 0.06856 HKLF 4 REM 273K in P2(1)/n REM R1 = 0.0823 for 1551 Fo > 4sig(Fo) and 0.1167 for all 2542 data REM 120 parameters refined using 0 restraints END WGHT 0.1371 0.5670 REM Highest difference peak 0.465, deepest hole -0.336, 1-sigma level 0.053 Q1 1 0.4605 0.9492 0.5536 11.00000 0.05 0.47 Q2 1 0.3395 0.9694 0.4983 11.00000 0.05 0.43 Q3 1 0.2823 0.8241 0.5973 11.00000 0.05 0.42 Q4 1 0.4013 0.9130 0.6459 11.00000 0.05 0.26 Q5 1 0.4240 0.5798 0.2988 11.00000 0.05 0.17 Q6 1 0.3504 0.6951 0.4407 11.00000 0.05 0.16 Q7 1 0.5620 0.5841 0.2730 11.00000 0.05 0.16 Q8 1 0.7124 0.5974 0.4970 11.00000 0.05 0.16 Q9 1 0.3086 0.7513 0.5156 11.00000 0.05 0.14 Q10 1 0.7740 0.6380 0.4252 11.00000 0.05 0.14 Q11 1 0.5258 0.5248 0.3185 11.00000 0.05 0.13 Q12 1 0.2680 0.4105 0.3085 11.00000 0.05 0.13 Q13 1 0.4932 0.7771 0.5011 11.00000 0.05 0.13 Q14 1 0.3426 0.4796 0.2583 11.00000 0.05 0.13 Q15 1 0.3508 0.7308 0.5207 11.00000 0.05 0.12 Q16 1 0.3113 0.3957 0.3239 11.00000 0.05 0.12 Q17 1 0.8169 0.5735 0.4556 11.00000 0.05 0.12 Q18 1 0.8182 0.6837 0.5830 11.00000 0.05 0.12 Q19 1 0.2102 0.3273 0.3975 11.00000 0.05 0.12 Q20 1 0.7650 0.5313 0.4608 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 0.2606(2) 0.3997(3) 0.34704(16) 0.0696(7) Uani 1 1 d . O2 O 0.5163(3) 0.5683(3) 0.30503(15) 0.0709(7) Uani 1 1 d . O3 O 0.7819(2) 0.5896(3) 0.45614(17) 0.0730(7) Uani 1 1 d . N1 N 0.3525(4) 0.8390(3) 0.5441(2) 0.0743(8) Uani 1 1 d . C1 C 0.1201(4) 0.4073(5) 0.3739(3) 0.0862(12) Uani 1 1 d . H1A H 0.0448 0.3571 0.3236 0.103 Uiso 1 1 calc R H1B H 0.0921 0.5198 0.3802 0.103 Uiso 1 1 calc R C2 C 0.2655(5) 0.4806(5) 0.2578(3) 0.0855(11) Uani 1 1 d . H2A H 0.2383 0.5939 0.2624 0.103 Uiso 1 1 calc R H2B H 0.1944 0.4312 0.2048 0.103 Uiso 1 1 calc R C3 C 0.4190(5) 0.4687(5) 0.2379(2) 0.0820(11) Uani 1 1 d . H3A H 0.4531 0.3569 0.2446 0.098 Uiso 1 1 calc R H3B H 0.4189 0.5039 0.1717 0.098 Uiso 1 1 calc R C4 C 0.6648(5) 0.5665(5) 0.2901(3) 0.0838(11) Uani 1 1 d . H4A H 0.6671 0.6076 0.2254 0.101 Uiso 1 1 calc R H4B H 0.7022 0.4558 0.2944 0.101 Uiso 1 1 calc R C5 C 0.7614(4) 0.6683(4) 0.3645(3) 0.0806(11) Uani 1 1 d . H5A H 0.8575 0.6851 0.3465 0.097 Uiso 1 1 calc R H5B H 0.7150 0.7735 0.3683 0.097 Uiso 1 1 calc R C6 C 0.8732(4) 0.6775(5) 0.5328(3) 0.0866(11) Uani 1 1 d . H6A H 0.8325 0.7857 0.5365 0.104 Uiso 1 1 calc R H6B H 0.9733 0.6881 0.5199 0.104 Uiso 1 1 calc R C7 C 0.4347(4) 0.7161(4) 0.5019(2) 0.0697(8) Uani 1 1 d . H7A H 0.4515 0.7534 0.4400 0.105 Uiso 1 1 calc R H7B H 0.3777 0.6173 0.4928 0.105 Uiso 1 1 calc R H7C H 0.5292 0.6965 0.5450 0.105 Uiso 1 1 calc R O4 O 0.2235(4) 0.8640(5) 0.5038(4) 0.1504(16) Uani 1 1 d . O5 O 0.4032(6) 0.8978(6) 0.6206(3) 0.169(2) Uani 1 1 d . 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 0.0643(13) 0.0685(13) 0.0700(13) -0.0041(10) -0.0002(10) 0.0107(10) O2 0.0899(16) 0.0679(13) 0.0591(12) -0.0051(10) 0.0253(11) 0.0072(11) O3 0.0717(14) 0.0624(12) 0.0895(16) -0.0012(11) 0.0273(11) -0.0061(10) N1 0.084(2) 0.0680(16) 0.0715(18) 0.0031(13) 0.0169(14) 0.0188(14) C1 0.0544(18) 0.086(2) 0.109(3) -0.025(2) -0.0062(17) 0.0027(16) C2 0.106(3) 0.070(2) 0.065(2) -0.0028(16) -0.0204(18) 0.0111(18) C3 0.126(3) 0.072(2) 0.0462(16) -0.0029(14) 0.0149(17) 0.008(2) C4 0.109(3) 0.084(2) 0.073(2) 0.0124(18) 0.053(2) 0.021(2) C5 0.080(2) 0.0705(19) 0.105(3) 0.0180(19) 0.051(2) 0.0070(16) C6 0.0580(18) 0.082(2) 0.123(3) -0.019(2) 0.0272(19) -0.0164(16) C7 0.0740(19) 0.0603(17) 0.076(2) -0.0035(14) 0.0176(15) 0.0145(14) O4 0.084(2) 0.148(3) 0.216(4) 0.023(3) 0.021(2) 0.042(2) O5 0.187(4) 0.178(4) 0.127(3) -0.074(3) -0.004(3) 0.069(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' 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 113.8(3) . . C4 O2 C3 112.8(3) . . C6 O3 C5 113.7(3) . . O5 N1 O4 121.1(4) . . O5 N1 C7 120.9(3) . . O4 N1 C7 117.4(4) . . O1 C1 C6 109.8(3) . 3_666 O1 C1 H1A 109.7 . . C6 C1 H1A 109.7 3_666 . O1 C1 H1B 109.7 . . C6 C1 H1B 109.7 3_666 . H1A C1 H1B 108.2 . . O1 C2 C3 109.3(3) . . O1 C2 H2A 109.8 . . C3 C2 H2A 109.8 . . O1 C2 H2B 109.8 . . C3 C2 H2B 109.8 . . H2A C2 H2B 108.3 . . O2 C3 C2 109.0(3) . . 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 110.1(3) . . O2 C4 H4A 109.6 . . C5 C4 H4A 109.6 . . O2 C4 H4B 109.6 . . C5 C4 H4B 109.6 . . H4A C4 H4B 108.2 . . O3 C5 C4 109.2(3) . . 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 110.0(3) . 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 1.409(4) . O1 C2 1.423(5) . O2 C4 1.412(4) . O2 C3 1.415(4) . O3 C6 1.416(4) . O3 C5 1.413(4) . N1 O5 1.180(4) . N1 O4 1.216(4) . N1 C7 1.454(4) . C1 C6 1.470(6) 3_666 C1 H1A 0.9700 . C1 H1B 0.9700 . C2 C3 1.486(6) . C2 H2A 0.9700 . C2 H2B 0.9700 . C3 H3A 0.9700 . C3 H3B 0.9700 . C4 C5 1.480(6) . C4 H4A 0.9700 . C4 H4B 0.9700 . C5 H5A 0.9700 . C5 H5B 0.9700 . C6 C1 1.470(6) 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 -179.2(3) 3_666 C1 O1 C2 C3 178.6(3) . C4 O2 C3 C2 -178.9(3) . O1 C2 C3 O2 -70.9(3) . C3 O2 C4 C5 -178.1(3) . C6 O3 C5 C4 -180.0(3) . O2 C4 C5 O3 71.2(3) . C5 O3 C6 C1 176.1(3) 3_666