#------------------------------------------------------------------------------ #$Date: 2014-04-01 12:37:31 +0200 (Tue, 01 Apr 2014) $ #$Revision: 108412 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/22/7112241.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_7112241 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 C4CC00849A _journal_volume 50 _journal_year 2014 _chemical_compound_source sigma _chemical_formula_moiety 'C12 H24 O6, 2(C H3 I)' _chemical_formula_sum 'C14 H30 I2 O6' _chemical_formula_weight 548.18 _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 106.751(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 9.0683(3) _cell_length_b 8.6955(2) _cell_length_c 14.2945(5) _cell_measurement_reflns_used 3014 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 24.66 _cell_measurement_theta_min 2.39 _cell_volume 1079.34(6) _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 273(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _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 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 8606 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 28.33 _diffrn_reflns_theta_min 2.39 _diffrn_source 'INCOATEC Mo micro source' _diffrn_source_type 'Bruker APEX II DUO QUAZAR' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.934 _exptl_absorpt_correction_T_max 0.8672 _exptl_absorpt_correction_T_min 0.6673 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'symmetry-related measurements' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plates _exptl_crystal_F_000 536 _exptl_crystal_recrystallization_method iodomethane _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 1.019 _refine_diff_density_min -0.804 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 2677 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.026 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0353 _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^)+(0.0328P)^2^+1.1312P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.0878 _reflns_number_gt 1954 _reflns_number_total 2677 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c4cc00849a2.cif _[local]_cod_data_source_block C_iodomethane_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 7112241 _iucr_refine_instruction_details ; TITL 273K in P2(1)/n CELL 0.71073 9.0683 8.6955 14.2945 90.000 106.751 90.000 ZERR 2.0000 0.0003 0.0002 0.0005 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O I UNIT 28 60 0 12 4 MERG 2 FMAP 2 GRID PLAN 20 TEMP 0 SIZE 0.15 0.15 0.05 OMIT 0 7 11 OMIT 0 5 16 HTAB CONF BOND$H L.S. 20 ACTA 52 WGHT 0.032800 1.131200 FVAR 0.12329 I1 5 0.315042 0.880235 0.055050 11.00000 0.10703 0.06500 = 0.07712 -0.00112 0.04799 0.01245 O3 4 0.298907 0.921058 0.488308 11.00000 0.07082 0.06044 = 0.09909 0.00137 0.03649 0.00680 O4 4 0.040770 0.934622 0.314322 11.00000 0.09933 0.07488 = 0.05602 0.00100 0.03352 -0.01775 O5 4 -0.231440 1.092241 0.327093 11.00000 0.06920 0.07261 = 0.06960 0.00648 0.00159 -0.01044 C6 1 -0.051498 1.027933 0.241223 11.00000 0.13235 0.08976 = 0.04367 -0.00023 0.02302 -0.02486 AFIX 23 H6A 2 -0.042610 0.996424 0.177977 11.00000 -1.20000 H6B 2 -0.018221 1.134113 0.252220 11.00000 -1.20000 AFIX 0 C8 1 0.198638 0.938713 0.317709 11.00000 0.11579 0.08656 = 0.08832 -0.01738 0.07374 -0.02219 AFIX 23 H8A 2 0.235153 1.044132 0.325033 11.00000 -1.20000 H8B 2 0.211164 0.898583 0.257144 11.00000 -1.20000 AFIX 0 C9 1 0.289520 0.845816 0.400447 11.00000 0.09089 0.06645 = 0.12416 -0.00265 0.06979 -0.00025 AFIX 23 H9A 2 0.241303 0.746106 0.399866 11.00000 -1.20000 H9B 2 0.392205 0.829692 0.394373 11.00000 -1.20000 AFIX 0 C10 1 -0.379999 1.081082 0.337517 11.00000 0.06334 0.08961 = 0.10054 0.01043 -0.00339 -0.00313 AFIX 23 H10A 2 -0.407229 0.973817 0.341110 11.00000 -1.20000 H10B 2 -0.453841 1.126961 0.281428 11.00000 -1.20000 AFIX 0 C13 1 -0.213727 1.013626 0.242929 11.00000 0.11020 0.08461 = 0.04728 0.00048 -0.00745 -0.01533 AFIX 23 H13A 2 -0.281982 1.058157 0.184062 11.00000 -1.20000 H13B 2 -0.240352 0.905971 0.245440 11.00000 -1.20000 AFIX 0 C14 1 0.384387 0.837947 0.572118 11.00000 0.05242 0.07610 = 0.14069 0.02040 0.02133 0.01468 AFIX 23 H14A 2 0.490335 0.827488 0.570948 11.00000 -1.20000 H14B 2 0.341305 0.735669 0.571231 11.00000 -1.20000 AFIX 0 C3 1 0.432300 0.714498 -0.005255 11.00000 0.07870 0.06445 = 0.07105 0.00157 0.02969 0.01314 AFIX 137 H3A 2 0.445164 0.752828 -0.065397 11.00000 -1.50000 H3B 2 0.373441 0.621081 -0.017633 11.00000 -1.50000 H3C 2 0.531484 0.694405 0.039911 11.00000 -1.50000 HKLF 4 REM 273K in P2(1)/n REM R1 = 0.0353 for 1954 Fo > 4sig(Fo) and 0.0512 for all 2677 data REM 101 parameters refined using 0 restraints END WGHT 0.0328 1.1317 REM Highest difference peak 1.019, deepest hole -0.804, 1-sigma level 0.069 Q1 1 0.2499 0.8449 0.0112 11.00000 0.05 1.02 Q2 1 0.3353 0.8389 0.1006 11.00000 0.05 0.76 Q3 1 0.3835 0.9076 0.0406 11.00000 0.05 0.53 Q4 1 0.2616 0.9433 0.0639 11.00000 0.05 0.36 Q5 1 -0.2768 1.1173 0.3696 11.00000 0.05 0.33 Q6 1 0.4628 0.6188 0.0407 11.00000 0.05 0.27 Q7 1 0.3718 0.8802 0.4995 11.00000 0.05 0.25 Q8 1 0.0890 0.9413 0.2664 11.00000 0.05 0.25 Q9 1 0.2607 0.9134 0.4961 11.00000 0.05 0.24 Q10 1 0.3812 0.8167 0.0114 11.00000 0.05 0.23 Q11 1 -0.3952 1.0946 0.3887 11.00000 0.05 0.21 Q12 1 -0.0675 0.9354 0.2935 11.00000 0.05 0.21 Q13 1 0.2864 0.9384 0.4285 11.00000 0.05 0.21 Q14 1 0.2496 0.9781 -0.0142 11.00000 0.05 0.19 Q15 1 0.3248 0.6916 -0.0211 11.00000 0.05 0.19 Q16 1 0.4629 0.8660 0.1133 11.00000 0.05 0.19 Q17 1 -0.2968 1.0212 0.2772 11.00000 0.05 0.19 Q18 1 0.1595 0.8438 0.4511 11.00000 0.05 0.18 Q19 1 0.2458 0.8049 0.4372 11.00000 0.05 0.18 Q20 1 0.5425 0.7876 -0.0042 11.00000 0.05 0.17 ; 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 I1 I 0.31504(4) 0.88024(3) 0.05505(2) 0.07856(14) Uani 1 1 d . O3 O 0.2989(3) 0.9211(3) 0.4883(2) 0.0743(8) Uani 1 1 d . O4 O 0.0408(4) 0.9346(3) 0.31432(19) 0.0744(8) Uani 1 1 d . O5 O -0.2314(3) 1.0922(3) 0.3271(2) 0.0743(8) Uani 1 1 d . C6 C -0.0515(6) 1.0279(6) 0.2412(3) 0.0891(14) Uani 1 1 d . H6A H -0.0426 0.9964 0.1780 0.107 Uiso 1 1 calc R H6B H -0.0182 1.1341 0.2522 0.107 Uiso 1 1 calc R C8 C 0.1986(6) 0.9387(6) 0.3177(3) 0.0876(14) Uani 1 1 d . H8A H 0.2352 1.0441 0.3250 0.105 Uiso 1 1 calc R H8B H 0.2112 0.8986 0.2571 0.105 Uiso 1 1 calc R C9 C 0.2895(6) 0.8458(5) 0.4004(4) 0.0857(14) Uani 1 1 d . H9A H 0.2413 0.7461 0.3999 0.103 Uiso 1 1 calc R H9B H 0.3922 0.8297 0.3944 0.103 Uiso 1 1 calc R C10 C -0.3800(5) 1.0811(6) 0.3375(4) 0.0902(15) Uani 1 1 d . H10A H -0.4072 0.9738 0.3411 0.108 Uiso 1 1 calc R H10B H -0.4538 1.1270 0.2814 0.108 Uiso 1 1 calc R C13 C -0.2137(6) 1.0136(6) 0.2429(3) 0.0870(14) Uani 1 1 d . H13A H -0.2820 1.0582 0.1841 0.104 Uiso 1 1 calc R H13B H -0.2404 0.9060 0.2454 0.104 Uiso 1 1 calc R C14 C 0.3844(5) 0.8379(6) 0.5721(4) 0.0911(15) Uani 1 1 d . H14A H 0.4903 0.8275 0.5709 0.109 Uiso 1 1 calc R H14B H 0.3413 0.7357 0.5712 0.109 Uiso 1 1 calc R C3 C 0.4323(5) 0.7145(5) -0.0053(3) 0.0697(10) Uani 1 1 d . H3A H 0.4452 0.7528 -0.0654 0.105 Uiso 1 1 calc R H3B H 0.3734 0.6211 -0.0176 0.105 Uiso 1 1 calc R H3C H 0.5315 0.6944 0.0399 0.105 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 I1 0.1070(3) 0.0650(2) 0.0771(2) -0.00112(13) 0.04799(17) 0.01245(15) O3 0.0708(17) 0.0604(16) 0.099(2) 0.0014(15) 0.0365(16) 0.0068(13) O4 0.099(2) 0.0749(17) 0.0560(15) 0.0010(13) 0.0335(15) -0.0177(16) O5 0.0692(17) 0.0726(18) 0.0696(17) 0.0065(13) 0.0016(14) -0.0104(14) C6 0.132(4) 0.090(3) 0.0437(19) 0.000(2) 0.023(2) -0.025(3) C8 0.116(4) 0.087(3) 0.088(3) -0.017(3) 0.074(3) -0.022(3) C9 0.091(3) 0.066(3) 0.124(4) -0.003(3) 0.070(3) 0.000(2) C10 0.063(3) 0.090(3) 0.101(4) 0.010(3) -0.003(2) -0.003(2) C13 0.110(4) 0.085(3) 0.047(2) 0.000(2) -0.007(2) -0.015(3) C14 0.052(2) 0.076(3) 0.141(5) 0.020(3) 0.021(3) 0.015(2) C3 0.079(3) 0.064(2) 0.071(2) 0.0016(19) 0.030(2) 0.013(2) 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' I I -0.4742 1.8119 '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 C9 O3 C14 113.4(4) . . C6 O4 C8 113.1(4) . . C10 O5 C13 113.6(4) . . O4 C6 C13 108.8(4) . . O4 C6 H6A 109.9 . . C13 C6 H6A 109.9 . . O4 C6 H6B 109.9 . . C13 C6 H6B 109.9 . . H6A C6 H6B 108.3 . . O4 C8 C9 109.8(3) . . O4 C8 H8A 109.7 . . C9 C8 H8A 109.7 . . O4 C8 H8B 109.7 . . C9 C8 H8B 109.7 . . H8A C8 H8B 108.2 . . O3 C9 C8 109.9(4) . . O3 C9 H9A 109.7 . . C8 C9 H9A 109.7 . . O3 C9 H9B 109.7 . . C8 C9 H9B 109.7 . . H9A C9 H9B 108.2 . . O5 C10 C14 109.2(4) . 3_576 O5 C10 H10A 109.8 . . C14 C10 H10A 109.8 3_576 . O5 C10 H10B 109.8 . . C14 C10 H10B 109.8 3_576 . H10A C10 H10B 108.3 . . O5 C13 C6 109.0(3) . . O5 C13 H13A 109.9 . . C6 C13 H13A 109.9 . . O5 C13 H13B 109.9 . . C6 C13 H13B 109.9 . . H13A C13 H13B 108.3 . . O3 C14 C10 110.4(4) . 3_576 O3 C14 H14A 109.6 . . C10 C14 H14A 109.6 3_576 . O3 C14 H14B 109.6 . . C10 C14 H14B 109.6 3_576 . H14A C14 H14B 108.1 . . I1 C3 H3A 109.5 . . I1 C3 H3B 109.5 . . H3A C3 H3B 109.5 . . I1 C3 H3C 109.5 . . H3A C3 H3C 109.5 . . H3B C3 H3C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 I1 C3 2.116(4) . O3 C9 1.397(6) . O3 C14 1.422(6) . O4 C6 1.395(5) . O4 C8 1.419(5) . O5 C10 1.401(6) . O5 C13 1.432(5) . C6 C13 1.484(7) . C6 H6A 0.9700 . C6 H6B 0.9700 . C8 C9 1.473(7) . C8 H8A 0.9700 . C8 H8B 0.9700 . C9 H9A 0.9700 . C9 H9B 0.9700 . C10 C14 1.482(8) 3_576 C10 H10A 0.9700 . C10 H10B 0.9700 . C13 H13A 0.9700 . C13 H13B 0.9700 . C14 C10 1.482(8) 3_576 C14 H14A 0.9700 . C14 H14B 0.9700 . C3 H3A 0.9600 . C3 H3B 0.9600 . C3 H3C 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 C8 O4 C6 C13 179.2(4) . C6 O4 C8 C9 176.3(4) . C14 O3 C9 C8 179.6(4) . O4 C8 C9 O3 -72.0(5) . C13 O5 C10 C14 178.4(4) 3_576 C10 O5 C13 C6 -177.9(4) . O4 C6 C13 O5 72.6(5) . C9 O3 C14 C10 -175.9(4) 3_576