#------------------------------------------------------------------------------ #$Date: 2016-03-26 12:48:58 +0100 (Sat, 26 Mar 2016) $ #$Revision: 180236 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/22/7112235.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_7112235 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 180K _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 100.907(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.2668(13) _cell_length_b 7.9623(11) _cell_length_c 13.7151(19) _cell_measurement_reflns_used 5223 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 28.16 _cell_measurement_theta_min 2.45 _cell_volume 993.7(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 180(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _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 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0159 _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 14545 _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 0.109 _exptl_absorpt_correction_T_max 0.9710 _exptl_absorpt_correction_T_min 0.9575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'symmetry-related measurements' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.291 _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 0.297 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2464 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0406 _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^)+(0.0397P)^2^+0.3802P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.1087 _reflns_number_gt 2045 _reflns_number_total 2464 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c4cc00849a2.cif _cod_data_source_block C_nitromethane_180K _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_sg_symbol_H-M 'P 21/n' _cod_database_code 7112235 #BEGIN Tags that were not found in dictionaries: _iucr_refine_instruction_details ; TITL 180K in P2(1)/n CELL 0.71073 9.2668 7.9623 13.7151 90.000 100.907 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 OMIT 0 6 6 FMAP 2 GRID PLAN 20 TEMP -93 SIZE 0.27 0.36 0.4 HTAB CONF BOND$H OMIT 0 3 11 L.S. 20 ACTA 52 WGHT 0.039700 0.380200 FVAR 0.21239 O1 4 0.263573 0.399897 0.344405 11.00000 0.02973 0.03583 = 0.03306 0.00069 0.00093 0.00535 O2 4 0.522118 0.563518 0.303542 11.00000 0.03689 0.03807 = 0.03042 -0.00579 0.00975 0.00005 O3 4 0.784008 0.579869 0.456367 11.00000 0.03730 0.03273 = 0.03821 0.00026 0.00751 -0.00505 O4 4 0.227839 0.867463 0.507923 11.00000 0.04053 0.07230 = 0.08321 0.00537 0.00408 0.02191 O5 4 0.415237 0.911448 0.622563 11.00000 0.07560 0.07492 = 0.06336 -0.03443 0.00031 0.01439 N1 3 0.355689 0.842942 0.546197 11.00000 0.03711 0.03272 = 0.03820 0.00395 0.00917 0.00550 C1 1 0.123121 0.415321 0.370126 11.00000 0.02589 0.04481 = 0.04641 -0.00731 -0.00131 0.00235 AFIX 23 H1A 2 0.047560 0.364276 0.317816 11.00000 -1.20000 H1B 2 0.098546 0.535414 0.376132 11.00000 -1.20000 AFIX 0 C2 1 0.272499 0.481598 0.253757 11.00000 0.04258 0.03627 = 0.03160 0.00095 -0.00688 0.00260 AFIX 23 H2A 2 0.247853 0.602036 0.257971 11.00000 -1.20000 H2B 2 0.201534 0.430654 0.198652 11.00000 -1.20000 AFIX 0 C3 1 0.425274 0.463447 0.234590 11.00000 0.05227 0.03595 = 0.02363 -0.00278 0.00486 -0.00022 AFIX 23 H3A 2 0.455945 0.344277 0.241653 11.00000 -1.20000 H3B 2 0.428588 0.499834 0.166026 11.00000 -1.20000 AFIX 0 C4 1 0.668336 0.557088 0.287009 11.00000 0.04437 0.04376 = 0.03410 0.00172 0.01944 0.00556 AFIX 23 H4A 2 0.671885 0.599770 0.219706 11.00000 -1.20000 H4B 2 0.703512 0.439430 0.291400 11.00000 -1.20000 AFIX 0 C5 1 0.765047 0.661814 0.363129 11.00000 0.03521 0.03656 = 0.04528 0.00701 0.01784 0.00006 AFIX 23 H5A 2 0.861694 0.678231 0.343736 11.00000 -1.20000 H5B 2 0.719787 0.773491 0.367607 11.00000 -1.20000 AFIX 0 C6 1 0.874605 0.672221 0.533090 11.00000 0.03019 0.04108 = 0.05133 -0.00820 0.00813 -0.00760 AFIX 23 H6A 2 0.835636 0.787514 0.535975 11.00000 -1.20000 H6B 2 0.975602 0.680020 0.519547 11.00000 -1.20000 AFIX 0 C7 1 0.440956 0.722465 0.498527 11.00000 0.03820 0.03309 = 0.04011 -0.00140 0.00858 0.00712 AFIX 137 H7A 2 0.382623 0.620561 0.480683 11.00000 -1.50000 H7B 2 0.531805 0.693654 0.544679 11.00000 -1.50000 H7C 2 0.465199 0.772987 0.438485 11.00000 -1.50000 HKLF 4 REM 180K in P2(1)/n REM R1 = 0.0406 for 2045 Fo > 4sig(Fo) and 0.0492 for all 2464 data REM 119 parameters refined using 0 restraints END WGHT 0.0387 0.4004 REM Highest difference peak 0.297, deepest hole -0.235, 1-sigma level 0.036 Q1 1 0.2891 0.9440 0.4957 11.00000 0.05 0.30 Q2 1 0.3570 0.4691 0.2537 11.00000 0.05 0.23 Q3 1 0.4282 0.9589 0.5609 11.00000 0.05 0.21 Q4 1 0.4676 0.9329 0.5770 11.00000 0.05 0.20 Q5 1 0.4139 0.9232 0.6449 11.00000 0.05 0.18 Q6 1 0.2478 0.8238 0.5603 11.00000 0.05 0.17 Q7 1 0.1286 0.3739 0.4170 11.00000 0.05 0.16 Q8 1 0.7178 0.6028 0.3274 11.00000 0.05 0.16 Q9 1 0.2134 0.7980 0.4597 11.00000 0.05 0.15 Q10 1 0.4496 0.6215 0.5401 11.00000 0.05 0.14 Q11 1 0.3668 0.8302 0.6155 11.00000 0.05 0.14 Q12 1 0.3745 0.6886 0.4349 11.00000 0.05 0.14 Q13 1 0.5846 0.5781 0.2854 11.00000 0.05 0.14 Q14 1 0.4026 0.7774 0.5176 11.00000 0.05 0.13 Q15 1 0.6772 0.5136 0.2282 11.00000 0.05 0.12 Q16 1 0.5315 0.7757 0.5024 11.00000 0.05 0.12 Q17 1 0.5480 0.4868 0.3323 11.00000 0.05 0.11 Q18 1 0.7242 0.6115 0.4988 11.00000 0.05 0.11 Q19 1 0.7250 0.5278 0.4694 11.00000 0.05 0.11 Q20 1 0.4479 0.4544 0.1830 11.00000 0.05 0.11 ; #END Tags that were not found in dictionaries 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 0.26357(10) 0.39990(12) 0.34440(7) 0.0335(2) Uani 1 1 d . O2 O 0.52212(10) 0.56352(12) 0.30354(7) 0.0347(2) Uani 1 1 d . O3 O 0.78401(11) 0.57987(12) 0.45637(7) 0.0360(2) Uani 1 1 d . O4 O 0.22784(13) 0.86746(18) 0.50792(11) 0.0663(4) Uani 1 1 d . O5 O 0.41524(17) 0.91145(19) 0.62256(11) 0.0730(4) Uani 1 1 d . N1 N 0.35569(13) 0.84294(15) 0.54620(9) 0.0357(3) Uani 1 1 d . C1 C 0.12312(15) 0.4153(2) 0.37013(11) 0.0401(3) Uani 1 1 d . H1A H 0.0476 0.3643 0.3178 0.048 Uiso 1 1 calc R H1B H 0.0985 0.5354 0.3761 0.048 Uiso 1 1 calc R C2 C 0.27250(16) 0.48160(19) 0.25376(11) 0.0386(3) Uani 1 1 d . H2A H 0.2479 0.6020 0.2580 0.046 Uiso 1 1 calc R H2B H 0.2015 0.4307 0.1987 0.046 Uiso 1 1 calc R C3 C 0.42527(17) 0.46345(18) 0.23459(10) 0.0376(3) Uani 1 1 d . H3A H 0.4559 0.3443 0.2417 0.045 Uiso 1 1 calc R H3B H 0.4286 0.4998 0.1660 0.045 Uiso 1 1 calc R C4 C 0.66834(16) 0.55709(19) 0.28701(10) 0.0392(3) Uani 1 1 d . H4A H 0.6719 0.5998 0.2197 0.047 Uiso 1 1 calc R H4B H 0.7035 0.4394 0.2914 0.047 Uiso 1 1 calc R C5 C 0.76505(15) 0.66181(18) 0.36313(11) 0.0377(3) Uani 1 1 d . H5A H 0.8617 0.6782 0.3437 0.045 Uiso 1 1 calc R H5B H 0.7198 0.7735 0.3676 0.045 Uiso 1 1 calc R C6 C 0.87460(15) 0.67222(19) 0.53309(11) 0.0408(3) Uani 1 1 d . H6A H 0.8356 0.7875 0.5360 0.049 Uiso 1 1 calc R H6B H 0.9756 0.6800 0.5195 0.049 Uiso 1 1 calc R C7 C 0.44096(16) 0.72247(18) 0.49853(11) 0.0370(3) Uani 1 1 d . H7A H 0.3826 0.6206 0.4807 0.055 Uiso 1 1 calc R H7B H 0.5318 0.6937 0.5447 0.055 Uiso 1 1 calc R H7C H 0.4652 0.7730 0.4385 0.055 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 0.0297(5) 0.0358(5) 0.0331(5) 0.0007(4) 0.0009(4) 0.0053(4) O2 0.0369(5) 0.0381(5) 0.0304(5) -0.0058(4) 0.0097(4) 0.0000(4) O3 0.0373(5) 0.0327(5) 0.0382(5) 0.0003(4) 0.0075(4) -0.0050(4) O4 0.0405(7) 0.0723(9) 0.0832(10) 0.0054(7) 0.0041(6) 0.0219(6) O5 0.0756(9) 0.0749(9) 0.0634(8) -0.0344(7) 0.0003(7) 0.0144(7) N1 0.0371(6) 0.0327(6) 0.0382(6) 0.0040(5) 0.0092(5) 0.0055(5) C1 0.0259(6) 0.0448(8) 0.0464(8) -0.0073(6) -0.0013(5) 0.0024(6) C2 0.0426(8) 0.0363(7) 0.0316(7) 0.0010(5) -0.0069(6) 0.0026(6) C3 0.0523(8) 0.0359(7) 0.0236(6) -0.0028(5) 0.0049(6) -0.0002(6) C4 0.0444(8) 0.0438(8) 0.0341(7) 0.0017(6) 0.0194(6) 0.0056(6) C5 0.0352(7) 0.0366(7) 0.0453(8) 0.0070(6) 0.0178(6) 0.0001(6) C6 0.0302(7) 0.0411(8) 0.0513(9) -0.0082(7) 0.0081(6) -0.0076(6) C7 0.0382(7) 0.0331(7) 0.0401(7) -0.0014(6) 0.0086(6) 0.0071(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 112.76(10) . . C4 O2 C3 112.12(10) . . C5 O3 C6 112.65(11) . . O5 N1 O4 123.04(14) . . O5 N1 C7 118.71(12) . . O4 N1 C7 118.25(13) . . O1 C1 C6 108.73(11) . 3_666 O1 C1 H1A 109.9 . . C6 C1 H1A 109.9 3_666 . O1 C1 H1B 109.9 . . C6 C1 H1B 109.9 3_666 . H1A C1 H1B 108.3 . . O1 C2 C3 108.89(11) . . 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 109.21(11) . . 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 109.47(11) . . O2 C4 H4A 109.8 . . C5 C4 H4A 109.8 . . O2 C4 H4B 109.8 . . C5 C4 H4B 109.8 . . H4A C4 H4B 108.2 . . O3 C5 C4 109.21(11) . . 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 108.86(11) . 3_666 O3 C6 H6A 109.9 . . C1 C6 H6A 109.9 3_666 . O3 C6 H6B 109.9 . . C1 C6 H6B 109.9 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 1.4168(16) . O1 C2 1.4194(17) . O2 C4 1.4164(16) . O2 C3 1.4190(16) . O3 C5 1.4166(17) . O3 C6 1.4207(17) . O4 N1 1.2174(16) . O5 N1 1.2167(17) . N1 C7 1.4722(17) . C1 C6 1.496(2) 3_666 C1 H1A 0.9900 . C1 H1B 0.9900 . C2 C3 1.495(2) . C2 H2A 0.9900 . C2 H2B 0.9900 . C3 H3A 0.9900 . C3 H3B 0.9900 . C4 C5 1.495(2) . C4 H4A 0.9900 . C4 H4B 0.9900 . C5 H5A 0.9900 . C5 H5B 0.9900 . C6 C1 1.496(2) 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 -179.19(11) 3_666 C1 O1 C2 C3 178.15(11) . C4 O2 C3 C2 -177.73(11) . O1 C2 C3 O2 -70.47(14) . C3 O2 C4 C5 -178.81(11) . C6 O3 C5 C4 -179.78(11) . O2 C4 C5 O3 71.77(14) . C5 O3 C6 C1 174.75(11) 3_666