#------------------------------------------------------------------------------ #$Date: 2014-11-01 09:06:37 +0200 (Sat, 01 Nov 2014) $ #$Revision: 126140 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/22/7112237.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_7112237 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 240K _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 101.313(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.1902(15) _cell_length_b 8.1108(13) _cell_length_c 13.853(2) _cell_measurement_reflns_used 3851 _cell_measurement_temperature 240(2) _cell_measurement_theta_max 27.73 _cell_measurement_theta_min 2.45 _cell_volume 1012.5(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 240(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 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0176 _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 14825 _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 0.107 _exptl_absorpt_correction_T_max 0.9716 _exptl_absorpt_correction_T_min 0.9583 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'symmetry-related measurements' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cubic prism' _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 0.393 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2509 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.113 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0604 _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^)+(0.0799P)^2^+0.4427P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1757 _refine_ls_wR_factor_ref 0.1930 _reflns_number_gt 1797 _reflns_number_total 2509 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4cc00849a2.cif _[local]_cod_data_source_block C_nitromethane_240K _[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 1012.6(3) _cod_database_code 7112237 _iucr_refine_instruction_details ; TITL 240K in P2(1)/n CELL 0.71073 9.1902 8.1108 13.8533 90.000 101.313 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 -33 SIZE 0.27 0.36 0.4 HTAB CONF BOND$H L.S. 20 ACTA 52 WGHT 0.079900 0.442700 FVAR 0.21507 O1 4 0.262217 0.399672 0.345796 11.00000 0.04802 0.05389 = 0.05392 -0.00213 0.00009 0.00886 O2 4 0.519161 0.566161 0.304377 11.00000 0.06425 0.05551 = 0.04697 -0.00586 0.01836 0.00286 O3 4 0.782799 0.585093 0.456362 11.00000 0.05593 0.05030 = 0.06493 0.00017 0.01733 -0.00595 O4 4 0.225509 0.865824 0.506147 11.00000 0.06492 0.11158 = 0.14788 0.00955 0.01112 0.03392 O5 4 0.410212 0.906558 0.620886 11.00000 0.12979 0.12882 = 0.10342 -0.06044 -0.00396 0.03710 N1 3 0.354007 0.841260 0.545036 11.00000 0.05974 0.05192 = 0.05817 0.00425 0.01374 0.01116 C1 1 0.122006 0.411679 0.372073 11.00000 0.04066 0.07040 = 0.07814 -0.01706 -0.00425 0.00327 AFIX 23 H1A 2 0.046274 0.361660 0.320746 11.00000 -1.20000 H1B 2 0.096210 0.527881 0.378422 11.00000 -1.20000 AFIX 0 C2 1 0.269150 0.481389 0.256100 11.00000 0.07300 0.05533 = 0.05071 -0.00027 -0.01266 0.00661 AFIX 23 H2A 2 0.243414 0.597979 0.260781 11.00000 -1.20000 H2B 2 0.197910 0.431723 0.201982 11.00000 -1.20000 AFIX 0 C3 1 0.421958 0.466478 0.236411 11.00000 0.09018 0.05620 = 0.03513 -0.00456 0.00770 0.00283 AFIX 23 H3A 2 0.454370 0.351230 0.243257 11.00000 -1.20000 H3B 2 0.423343 0.502217 0.169022 11.00000 -1.20000 AFIX 0 C4 1 0.666362 0.562035 0.288559 11.00000 0.07784 0.06533 = 0.05526 0.00627 0.03559 0.01292 AFIX 23 H4A 2 0.669224 0.604062 0.222633 11.00000 -1.20000 H4B 2 0.702634 0.448130 0.292789 11.00000 -1.20000 AFIX 0 C5 1 0.762923 0.664916 0.363943 11.00000 0.05889 0.05531 = 0.07716 0.01296 0.03491 0.00370 AFIX 23 H5A 2 0.859381 0.681594 0.345322 11.00000 -1.20000 H5B 2 0.717044 0.773116 0.368002 11.00000 -1.20000 AFIX 0 C6 1 0.873753 0.674622 0.533046 11.00000 0.04606 0.06408 = 0.08944 -0.01399 0.01832 -0.01332 AFIX 23 H6A 2 0.834068 0.786165 0.536426 11.00000 -1.20000 H6B 2 0.974400 0.683712 0.519886 11.00000 -1.20000 AFIX 0 C7 1 0.437966 0.719579 0.500272 11.00000 0.05898 0.04965 = 0.06056 -0.00234 0.01419 0.01108 AFIX 137 H7A 2 0.456956 0.762369 0.438536 11.00000 -1.50000 H7B 2 0.381067 0.618389 0.488083 11.00000 -1.50000 H7C 2 0.531524 0.697327 0.544525 11.00000 -1.50000 HKLF 4 REM 240K in P2(1)/n REM R1 = 0.0604 for 1797 Fo > 4sig(Fo) and 0.0821 for all 2509 data REM 119 parameters refined using 0 restraints END WGHT 0.0799 0.4427 REM Highest difference peak 0.393, deepest hole -0.334, 1-sigma level 0.044 Q1 1 0.3036 0.9547 0.4919 11.00000 0.05 0.39 Q2 1 0.4480 0.9519 0.5573 11.00000 0.05 0.34 Q3 1 0.2980 0.8399 0.6038 11.00000 0.05 0.32 Q4 1 0.4166 0.9124 0.6441 11.00000 0.05 0.24 Q5 1 0.3794 0.6880 0.4314 11.00000 0.05 0.16 Q6 1 0.5657 0.5880 0.2788 11.00000 0.05 0.15 Q7 1 0.2255 0.7804 0.4519 11.00000 0.05 0.15 Q8 1 0.4569 0.6194 0.5482 11.00000 0.05 0.15 Q9 1 0.3551 0.4872 0.2564 11.00000 0.05 0.15 Q10 1 0.5377 0.9121 0.5166 11.00000 0.05 0.14 Q11 1 0.7266 0.6051 0.5008 11.00000 0.05 0.13 Q12 1 0.7623 0.5065 0.4662 11.00000 0.05 0.12 Q13 1 0.8608 0.6761 0.5814 11.00000 0.05 0.12 Q14 1 0.6991 0.5054 0.2293 11.00000 0.05 0.12 Q15 1 0.2866 0.4550 0.3583 11.00000 0.05 0.12 Q16 1 0.5280 0.5223 0.3202 11.00000 0.05 0.12 Q17 1 0.5337 0.7740 0.5155 11.00000 0.05 0.11 Q18 1 0.8480 0.5752 0.4655 11.00000 0.05 0.11 Q19 1 0.7613 0.6465 0.4280 11.00000 0.05 0.11 Q20 1 0.5227 0.5877 0.3396 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 0.26222(16) 0.39967(19) 0.34580(11) 0.0533(4) Uani 1 1 d . O2 O 0.51916(17) 0.56616(19) 0.30438(11) 0.0546(4) Uani 1 1 d . O3 O 0.78280(17) 0.58509(19) 0.45636(12) 0.0563(4) Uani 1 1 d . O4 O 0.2255(3) 0.8658(3) 0.5061(2) 0.1095(9) Uani 1 1 d . O5 O 0.4102(3) 0.9066(4) 0.6209(2) 0.1243(11) Uani 1 1 d . N1 N 0.3540(2) 0.8413(2) 0.54504(15) 0.0563(5) Uani 1 1 d . C1 C 0.1220(2) 0.4117(3) 0.3721(2) 0.0652(7) Uani 1 1 d . H1A H 0.0463 0.3617 0.3207 0.078 Uiso 1 1 calc R H1B H 0.0962 0.5279 0.3784 0.078 Uiso 1 1 calc R C2 C 0.2692(3) 0.4814(3) 0.25610(18) 0.0631(7) Uani 1 1 d . H2A H 0.2434 0.5980 0.2608 0.076 Uiso 1 1 calc R H2B H 0.1979 0.4317 0.2020 0.076 Uiso 1 1 calc R C3 C 0.4220(3) 0.4665(3) 0.23641(16) 0.0611(6) Uani 1 1 d . H3A H 0.4544 0.3512 0.2433 0.073 Uiso 1 1 calc R H3B H 0.4233 0.5022 0.1690 0.073 Uiso 1 1 calc R C4 C 0.6664(3) 0.5620(3) 0.28856(18) 0.0631(6) Uani 1 1 d . H4A H 0.6692 0.6041 0.2226 0.076 Uiso 1 1 calc R H4B H 0.7026 0.4481 0.2928 0.076 Uiso 1 1 calc R C5 C 0.7629(3) 0.6649(3) 0.36394(19) 0.0609(6) Uani 1 1 d . H5A H 0.8594 0.6816 0.3453 0.073 Uiso 1 1 calc R H5B H 0.7170 0.7731 0.3680 0.073 Uiso 1 1 calc R C6 C 0.8738(3) 0.6746(3) 0.5330(2) 0.0658(7) Uani 1 1 d . H6A H 0.8341 0.7862 0.5364 0.079 Uiso 1 1 calc R H6B H 0.9744 0.6837 0.5199 0.079 Uiso 1 1 calc R C7 C 0.4380(3) 0.7196(3) 0.50027(18) 0.0561(6) Uani 1 1 d . H7A H 0.4570 0.7624 0.4385 0.084 Uiso 1 1 calc R H7B H 0.3811 0.6184 0.4881 0.084 Uiso 1 1 calc R H7C H 0.5315 0.6973 0.5445 0.084 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 0.0480(8) 0.0539(9) 0.0539(9) -0.0021(7) 0.0001(6) 0.0089(6) O2 0.0643(10) 0.0555(9) 0.0470(8) -0.0059(7) 0.0184(7) 0.0029(7) O3 0.0559(9) 0.0503(8) 0.0649(10) 0.0002(7) 0.0173(7) -0.0059(7) O4 0.0649(13) 0.1116(19) 0.148(2) 0.0095(16) 0.0111(13) 0.0339(12) O5 0.130(2) 0.129(2) 0.1034(19) -0.0604(17) -0.0040(16) 0.0371(18) N1 0.0597(12) 0.0519(10) 0.0582(11) 0.0043(9) 0.0137(9) 0.0112(9) C1 0.0407(11) 0.0704(15) 0.0781(17) -0.0171(13) -0.0043(10) 0.0033(10) C2 0.0730(16) 0.0553(13) 0.0507(12) -0.0003(10) -0.0127(11) 0.0066(11) C3 0.0902(18) 0.0562(13) 0.0351(10) -0.0046(9) 0.0077(11) 0.0028(12) C4 0.0778(16) 0.0653(14) 0.0553(13) 0.0063(11) 0.0356(12) 0.0129(12) C5 0.0589(13) 0.0553(13) 0.0772(16) 0.0130(11) 0.0349(12) 0.0037(10) C6 0.0461(12) 0.0641(14) 0.0894(19) -0.0140(13) 0.0183(12) -0.0133(11) C7 0.0590(13) 0.0496(12) 0.0606(13) -0.0023(10) 0.0142(10) 0.0111(10) 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 113.19(18) . . C4 O2 C3 112.42(18) . . C5 O3 C6 113.37(19) . . O5 N1 O4 122.0(2) . . O5 N1 C7 119.8(2) . . O4 N1 C7 118.1(2) . . O1 C1 C6 109.26(19) . 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 108.3 . . O1 C2 C3 109.18(18) . . 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 109.06(19) . . 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 109.60(18) . . 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 109.40(19) . . O3 C5 H5A 109.8 . . C4 C5 H5A 109.8 . . O3 C5 H5B 109.8 . . C4 C5 H5B 109.8 . . H5A C5 H5B 108.2 . . O3 C6 C1 109.4(2) . 3_666 O3 C6 H6A 109.8 . . C1 C6 H6A 109.8 3_666 . O3 C6 H6B 109.8 . . C1 C6 H6B 109.8 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(3) . O1 C2 1.421(3) . O2 C4 1.413(3) . O2 C3 1.417(3) . O3 C5 1.414(3) . O3 C6 1.416(3) . O4 N1 1.214(3) . O5 N1 1.199(3) . N1 C7 1.463(3) . C1 C6 1.483(4) 3_666 C1 H1A 0.9800 . C1 H1B 0.9800 . C2 C3 1.487(4) . C2 H2A 0.9800 . C2 H2B 0.9800 . C3 H3A 0.9800 . C3 H3B 0.9800 . C4 C5 1.487(4) . C4 H4A 0.9800 . C4 H4B 0.9800 . C5 H5A 0.9800 . C5 H5B 0.9800 . C6 C1 1.483(4) 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 -179.12(19) 3_666 C1 O1 C2 C3 178.19(19) . C4 O2 C3 C2 -178.36(19) . O1 C2 C3 O2 -70.9(2) . C3 O2 C4 C5 -178.34(19) . C6 O3 C5 C4 -179.99(19) . O2 C4 C5 O3 71.4(2) . C5 O3 C6 C1 175.42(18) 3_666