#------------------------------------------------------------------------------ #$Date: 2017-09-19 09:31:49 +0300 (Tue, 19 Sep 2017) $ #$Revision: 201022 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/92/7229208.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_7229208 loop_ _publ_author_name 'Pereira, Jorge F. B.' 'Barber, Patrick S.' 'Kelley, Steven Paul' 'Berton, Paula' 'Rogers, Robin D.' _publ_section_title ; Double Salt Ionic Liquids Based on 1-Ethyl-3-Methylimidazolium Acetate and Hydroxyl-Functionalized Ammonium Acetates: Strong Effects of Weak Interactions ; _journal_name_full 'Phys. Chem. Chem. Phys.' _journal_paper_doi 10.1039/C7CP05710E _journal_year 2017 _chemical_formula_sum 'C7 H17 N O3' _chemical_formula_weight 163.21 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-08-21 deposited with the CCDC. 2017-09-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.612(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.7116(4) _cell_length_b 7.1277(4) _cell_length_c 8.4076(5) _cell_measurement_reflns_used 6074 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 33.12 _cell_measurement_theta_min 2.71 _cell_volume 450.98(4) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_unetI/netI 0.0266 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _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 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 11571 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 33.177 _diffrn_reflns_theta_min 2.482 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_correction_T_min 0.6206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker AXScale' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_description shard _exptl_crystal_F_000 180 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.020 _exptl_crystal_size_min 0.010 _refine_diff_density_max 0.312 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 1459 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.3(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 151 _refine_ls_number_reflns 3417 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0290 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.0114P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.0787 _reflns_Friedel_coverage 0.867 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.993 _reflns_number_gt 3264 _reflns_number_total 3417 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7cp05710e2.cif _cod_data_source_block ChoOAc _cod_database_code 7229208 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.989 _shelx_estimated_absorpt_t_max 0.999 _shelx_res_file ; p2.res created by SHELXL-2014/7 TITL p2 in P2(1) CELL 0.71073 7.7116 7.1277 8.4076 90.000 102.612 90.000 ZERR 2.00 0.0004 0.0004 0.0005 0.000 0.002 0.000 LATT -1 SYMM -X, 0.5+Y, -Z SFAC C H N O UNIT 14 34 2 6 L.S. 20 ACTA BOND FMAP 2 PLAN 5 SIZE 0.01 0.02 0.12 TEMP -173.000 WGHT 0.050600 0.011400 FVAR 0.67517 O1 4 0.480215 0.191477 0.881715 11.00000 0.01608 0.02461 = 0.04984 -0.00916 0.00496 0.00070 H1C 2 0.541319 0.114626 0.843472 11.00000 -1.50000 O2 4 0.706352 -0.035353 0.780837 11.00000 0.01998 0.02365 = 0.03313 -0.00610 0.00640 -0.00108 O3 4 0.836798 -0.258468 0.665047 11.00000 0.02144 0.03042 = 0.03698 -0.00360 0.01036 0.00373 N1 3 0.067755 0.296116 0.762104 11.00000 0.01362 0.01599 = 0.01564 -0.00046 0.00247 -0.00110 C5 1 0.187090 0.460853 0.757653 11.00000 0.01797 0.01680 = 0.03057 0.00172 0.00352 -0.00330 H5A 2 0.116121 0.563161 0.742606 11.00000 -1.50000 H5B 2 0.239418 0.439580 0.663273 11.00000 -1.50000 H5C 2 0.275384 0.458034 0.853554 11.00000 -1.50000 C4 1 -0.021566 0.317142 0.902419 11.00000 0.01859 0.02419 = 0.01730 -0.00225 0.00564 0.00231 H4A 2 -0.090391 0.425899 0.884654 11.00000 -1.50000 H4B 2 0.069378 0.327993 0.998651 11.00000 -1.50000 H4C 2 -0.100163 0.213139 0.898635 11.00000 -1.50000 C3 1 -0.074492 0.293972 0.608142 11.00000 0.01826 0.02560 = 0.01627 0.00077 -0.00041 -0.00090 H3A 2 -0.140752 0.408903 0.603260 11.00000 -1.50000 H3B 2 -0.153536 0.194492 0.616668 11.00000 -1.50000 H3C 2 -0.021390 0.285730 0.521909 11.00000 -1.50000 C1 1 0.167917 0.112203 0.771370 11.00000 0.01753 0.01536 = 0.01948 -0.00213 0.00443 0.00028 H1A 2 0.206319 0.097210 0.666394 11.00000 -1.20000 H1B 2 0.083925 0.017148 0.773282 11.00000 -1.20000 C2 1 0.330216 0.095681 0.911445 11.00000 0.01849 0.02366 = 0.02391 -0.00127 0.00213 0.00407 H2A 2 0.307446 0.143551 1.008510 11.00000 -1.20000 H2B 2 0.352557 -0.037013 0.924244 11.00000 -1.20000 C7 1 0.702295 -0.178617 0.692580 11.00000 0.01537 0.01931 = 0.01777 0.00293 0.00338 -0.00064 C6 1 0.522823 -0.262863 0.617280 11.00000 0.02072 0.04540 = 0.04059 -0.01313 0.00266 -0.00919 H6C 2 0.511233 -0.267426 0.492915 11.00000 -1.50000 H6B 2 0.430007 -0.202823 0.645530 11.00000 -1.50000 H6A 2 0.521202 -0.392407 0.670336 11.00000 -1.50000 HKLF 4 REM p2 in P2(1) REM R1 = 0.0290 for 3264 Fo > 4sig(Fo) and 0.0306 for all 3417 data REM 151 parameters refined using 1 restraints END WGHT 0.0512 0.0127 REM Highest difference peak 0.312, deepest hole -0.147, 1-sigma level 0.035 Q1 1 0.2471 0.1007 0.8450 11.00000 0.05 0.31 Q2 1 0.0046 0.2916 0.6850 11.00000 0.05 0.26 Q3 1 0.6178 -0.2203 0.6526 11.00000 0.05 0.26 Q4 1 0.1215 0.2068 0.7621 11.00000 0.05 0.23 Q5 1 0.7810 -0.1963 0.6710 11.00000 0.05 0.21 ; _shelx_res_checksum 33400 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_adp O1 O 0.48022(10) 0.19148(12) 0.88172(13) 0.0305(2) Uani 1 1 d . H1C H 0.541(3) 0.115(4) 0.843(3) 0.046 Uiso 1 1 d U O2 O 0.70635(10) -0.03535(12) 0.78084(11) 0.02549(16) Uani 1 1 d . O3 O 0.83680(11) -0.25847(13) 0.66505(11) 0.02900(18) Uani 1 1 d . N1 N 0.06775(10) 0.29612(11) 0.76210(9) 0.01519(13) Uani 1 1 d . C5 C 0.18709(13) 0.46085(15) 0.75765(13) 0.02205(18) Uani 1 1 d . H5A H 0.116(3) 0.563(3) 0.743(2) 0.033 Uiso 1 1 d U H5B H 0.239(3) 0.440(3) 0.663(2) 0.033 Uiso 1 1 d U H5C H 0.275(3) 0.458(3) 0.854(2) 0.033 Uiso 1 1 d U C4 C -0.02157(13) 0.31714(15) 0.90242(11) 0.01977(17) Uani 1 1 d . H4A H -0.090(2) 0.426(3) 0.885(2) 0.030 Uiso 1 1 d U H4B H 0.069(2) 0.328(3) 0.999(2) 0.030 Uiso 1 1 d U H4C H -0.100(3) 0.213(3) 0.899(2) 0.030 Uiso 1 1 d U C3 C -0.07449(12) 0.29397(16) 0.60814(11) 0.02068(17) Uani 1 1 d . H3A H -0.141(3) 0.409(3) 0.603(2) 0.031 Uiso 1 1 d U H3B H -0.154(3) 0.194(3) 0.617(2) 0.031 Uiso 1 1 d U H3C H -0.021(3) 0.286(3) 0.522(2) 0.031 Uiso 1 1 d U C1 C 0.16792(12) 0.11220(13) 0.77137(11) 0.01740(16) Uani 1 1 d . H1A H 0.206(2) 0.097(2) 0.6664(19) 0.021 Uiso 1 1 d U H1B H 0.084(2) 0.017(2) 0.773(2) 0.021 Uiso 1 1 d U C2 C 0.33022(13) 0.09568(16) 0.91144(12) 0.02240(18) Uani 1 1 d . H2A H 0.307(3) 0.144(3) 1.009(2) 0.027 Uiso 1 1 d U H2B H 0.353(2) -0.037(3) 0.924(2) 0.027 Uiso 1 1 d U C7 C 0.70230(12) -0.17862(13) 0.69258(11) 0.01752(16) Uani 1 1 d . C6 C 0.52282(16) -0.2629(2) 0.61728(18) 0.0362(3) Uani 1 1 d . H6C H 0.511(4) -0.267(4) 0.493(3) 0.054 Uiso 1 1 d U H6B H 0.430(4) -0.203(4) 0.646(3) 0.054 Uiso 1 1 d U H6A H 0.521(3) -0.392(4) 0.670(3) 0.054 Uiso 1 1 d U 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 0.0161(3) 0.0246(4) 0.0498(5) -0.0092(3) 0.0050(3) 0.0007(3) O2 0.0200(3) 0.0237(3) 0.0331(4) -0.0061(3) 0.0064(3) -0.0011(3) O3 0.0214(3) 0.0304(4) 0.0370(4) -0.0036(3) 0.0104(3) 0.0037(3) N1 0.0136(3) 0.0160(3) 0.0156(3) -0.0005(2) 0.0025(2) -0.0011(2) C5 0.0180(4) 0.0168(4) 0.0306(5) 0.0017(3) 0.0035(3) -0.0033(3) C4 0.0186(4) 0.0242(4) 0.0173(3) -0.0022(3) 0.0056(3) 0.0023(3) C3 0.0183(4) 0.0256(4) 0.0163(3) 0.0008(3) -0.0004(3) -0.0009(3) C1 0.0175(3) 0.0154(3) 0.0195(4) -0.0021(3) 0.0044(3) 0.0003(3) C2 0.0185(4) 0.0237(4) 0.0239(4) -0.0013(3) 0.0021(3) 0.0041(3) C7 0.0154(3) 0.0193(4) 0.0178(3) 0.0029(3) 0.0034(3) -0.0006(3) C6 0.0207(5) 0.0454(7) 0.0406(7) -0.0131(5) 0.0027(4) -0.0092(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 C5 N1 C4 109.39(8) C5 N1 C3 108.87(7) C4 N1 C3 107.74(7) C5 N1 C1 111.75(7) C4 N1 C1 111.29(7) C3 N1 C1 107.67(7) N1 C1 C2 115.47(7) O1 C2 C1 113.09(9) O3 C7 O2 124.37(9) O3 C7 C6 117.53(9) O2 C7 C6 118.09(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.4117(14) O2 C7 1.2586(12) O3 C7 1.2483(11) N1 C5 1.4974(12) N1 C4 1.4978(12) N1 C3 1.5030(11) N1 C1 1.5149(12) C1 C2 1.5243(13) C7 C6 1.5147(15)