data_global _journal_name_full 'Green Chemistry' _journal_coden_Cambridge 1048 _publ_contact_author_name 'Robin D Rogers' _publ_contact_author_email RDROGERS@BAMA.UA.EDU _publ_section_title ; New Hydrogen Carbonate Precursors for Efficient and Byproduct-Free Syntheses of Ionic Liquids Based on 1,2,3-Trimethylimidazolium and N,N-Dimethylpyrrolidinium Cores. ; loop_ _publ_author_name 'Robin D Rogers' 'Christopher Hines' 'Marcin Smiglak' # Attachment 'Rogers_New_HCO3_Precursors_11-18-09.cif' data_[1,2,3-triMeIM][MeCO3] _database_code_depnum_ccdc_archive 'CCDC 752754' #TrackingRef 'Rogers_New_HCO3_Precursors_11-18-09.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (1,2,3-triMeIM)(MeCO3) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N2 O3' _chemical_formula_weight 186.21 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 6.8805(6) _cell_length_b 11.6254(10) _cell_length_c 11.9614(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.229(2) _cell_angle_gamma 90.00 _cell_volume 951.13(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4168 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.19 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9707 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details '(SADABS, Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6361 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0202 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2219 _reflns_number_gt 1953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.2417P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2219 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0510 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.08588(16) 0.72300(9) 0.48332(8) 0.0353(3) Uani 1 1 d . . . O2 O 0.90907(16) 0.74459(9) 0.62773(9) 0.0376(3) Uani 1 1 d . . . O3 O 1.10928(15) 0.59728(9) 0.62719(8) 0.0362(3) Uani 1 1 d . . . N1 N 0.58048(16) 0.88738(9) 0.38828(9) 0.0247(2) Uani 1 1 d . . . N3 N 0.57995(15) 1.06474(9) 0.33617(9) 0.0243(2) Uani 1 1 d . . . C1 C 0.5202(2) 0.76819(13) 0.40444(13) 0.0341(3) Uani 1 1 d . . . H1A H 0.399(3) 0.7692(15) 0.4328(16) 0.041(5) Uiso 1 1 d . . . H1B H 0.619(3) 0.7310(16) 0.4546(17) 0.047(5) Uiso 1 1 d . . . H1C H 0.505(3) 0.7300(16) 0.3363(16) 0.043(5) Uiso 1 1 d . . . C2 C 0.46707(18) 0.97168(11) 0.34218(10) 0.0246(3) Uani 1 1 d . . . C3 C 0.5156(2) 1.17576(12) 0.28639(13) 0.0332(3) Uani 1 1 d . . . H3A H 0.401(3) 1.2009(17) 0.3176(16) 0.047(5) Uiso 1 1 d . . . H3B H 0.616(3) 1.2314(16) 0.3061(16) 0.045(5) Uiso 1 1 d . . . H3C H 0.484(3) 1.1681(15) 0.2065(16) 0.041(4) Uiso 1 1 d . . . C4 C 0.76982(19) 1.03738(12) 0.37703(11) 0.0277(3) Uani 1 1 d . . . H4A H 0.873(2) 1.0945(14) 0.3777(13) 0.035(4) Uiso 1 1 d . . . C5 C 0.77007(19) 0.92651(12) 0.40957(11) 0.0281(3) Uani 1 1 d . . . H5A H 0.873(3) 0.8733(14) 0.4431(14) 0.038(4) Uiso 1 1 d . . . C6 C 0.2574(2) 0.96250(15) 0.30152(14) 0.0364(3) Uani 1 1 d . . . H6A H 0.243(3) 0.9345(18) 0.2248(19) 0.059(6) Uiso 1 1 d . . . H6B H 0.196(3) 1.0323(19) 0.3036(17) 0.058(6) Uiso 1 1 d . . . H6C H 0.188(3) 0.9045(18) 0.3488(18) 0.061(6) Uiso 1 1 d . . . C7 C 1.02847(19) 0.69527(11) 0.57392(11) 0.0253(3) Uani 1 1 d . . . C8 C 1.2504(3) 0.53669(14) 0.57118(15) 0.0404(4) Uani 1 1 d . . . H8A H 1.203(3) 0.5182(18) 0.4923(19) 0.062(6) Uiso 1 1 d . . . H8B H 1.369(4) 0.584(2) 0.5668(19) 0.067(6) Uiso 1 1 d . . . H8C H 1.283(3) 0.464(2) 0.612(2) 0.076(7) Uiso 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 0.0404(6) 0.0363(5) 0.0300(5) 0.0086(4) 0.0079(4) 0.0047(4) O2 0.0351(6) 0.0414(6) 0.0378(6) 0.0031(4) 0.0110(4) 0.0083(4) O3 0.0426(6) 0.0344(5) 0.0331(5) 0.0108(4) 0.0102(4) 0.0099(4) N1 0.0244(5) 0.0276(5) 0.0223(5) 0.0001(4) 0.0030(4) 0.0000(4) N3 0.0235(5) 0.0262(5) 0.0230(5) -0.0021(4) 0.0012(4) 0.0035(4) C1 0.0371(8) 0.0300(7) 0.0353(8) 0.0034(6) 0.0041(6) -0.0060(6) C2 0.0224(6) 0.0306(6) 0.0214(6) -0.0044(5) 0.0046(5) 0.0022(5) C3 0.0346(8) 0.0290(7) 0.0348(7) 0.0025(6) -0.0009(6) 0.0074(6) C4 0.0219(6) 0.0303(7) 0.0302(7) -0.0022(5) -0.0009(5) -0.0001(5) C5 0.0234(6) 0.0311(7) 0.0287(6) 0.0005(5) -0.0023(5) 0.0011(5) C6 0.0211(7) 0.0463(9) 0.0413(8) -0.0064(7) 0.0014(6) 0.0024(6) C7 0.0238(6) 0.0253(6) 0.0257(6) 0.0010(5) -0.0015(5) -0.0025(5) C8 0.0453(9) 0.0313(8) 0.0457(9) 0.0040(7) 0.0101(7) 0.0116(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2358(16) . ? O2 C7 1.2381(16) . ? O3 C7 1.3913(16) . ? O3 C8 1.4244(18) . ? N1 C2 1.3343(17) . ? N1 C5 1.3789(17) . ? N1 C1 1.4651(18) . ? N3 C2 1.3382(17) . ? N3 C4 1.3814(16) . ? N3 C3 1.4693(17) . ? C1 H1A 0.934(19) . ? C1 H1B 0.96(2) . ? C1 H1C 0.924(19) . ? C2 C6 1.4756(19) . ? C3 H3A 0.952(19) . ? C3 H3B 0.96(2) . ? C3 H3C 0.961(19) . ? C4 C5 1.3464(19) . ? C4 H4A 0.972(17) . ? C5 H5A 0.991(17) . ? C6 H6A 0.97(2) . ? C6 H6B 0.92(2) . ? C6 H6C 1.03(2) . ? C8 H8A 0.99(2) . ? C8 H8B 0.99(2) . ? C8 H8C 0.99(2) . ? 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 _geom_angle_publ_flag C7 O3 C8 116.64(11) . . ? C2 N1 C5 109.46(11) . . ? C2 N1 C1 126.01(12) . . ? C5 N1 C1 124.29(12) . . ? C2 N3 C4 109.09(11) . . ? C2 N3 C3 125.51(12) . . ? C4 N3 C3 125.26(12) . . ? N1 C1 H1A 108.2(11) . . ? N1 C1 H1B 108.5(11) . . ? H1A C1 H1B 112.3(16) . . ? N1 C1 H1C 110.1(11) . . ? H1A C1 H1C 107.9(17) . . ? H1B C1 H1C 109.8(16) . . ? N1 C2 N3 107.41(11) . . ? N1 C2 C6 126.17(13) . . ? N3 C2 C6 126.39(13) . . ? N3 C3 H3A 109.6(12) . . ? N3 C3 H3B 108.5(11) . . ? H3A C3 H3B 107.5(16) . . ? N3 C3 H3C 110.3(11) . . ? H3A C3 H3C 108.3(16) . . ? H3B C3 H3C 112.7(15) . . ? C5 C4 N3 107.11(12) . . ? C5 C4 H4A 132.3(10) . . ? N3 C4 H4A 120.6(10) . . ? C4 C5 N1 106.91(12) . . ? C4 C5 H5A 133.9(10) . . ? N1 C5 H5A 119.2(10) . . ? C2 C6 H6A 109.5(12) . . ? C2 C6 H6B 111.3(13) . . ? H6A C6 H6B 108.8(18) . . ? C2 C6 H6C 111.1(12) . . ? H6A C6 H6C 107.1(17) . . ? H6B C6 H6C 108.9(17) . . ? O1 C7 O2 128.93(13) . . ? O1 C7 O3 117.73(12) . . ? O2 C7 O3 113.32(11) . . ? O3 C8 H8A 112.8(12) . . ? O3 C8 H8B 111.0(13) . . ? H8A C8 H8B 104.9(18) . . ? O3 C8 H8C 108.8(13) . . ? H8A C8 H8C 108.5(18) . . ? H8B C8 H8C 110.8(19) . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.177 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.043 data_[1,2,3-triMeIM][HCO3]H2O _database_code_depnum_ccdc_archive 'CCDC 752755' #TrackingRef 'Rogers_New_HCO3_Precursors_11-18-09.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (1,2,3-triMeIM)(HCO3)H2O _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H14 N2 O4' _chemical_formula_weight 190.20 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 7.479(2) _cell_length_b 13.289(4) _cell_length_c 9.636(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.011(5) _cell_angle_gamma 90.00 _cell_volume 954.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1200 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 25.12 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9787 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6463 _diffrn_reflns_av_R_equivalents 0.0900 _diffrn_reflns_av_sigmaI/netI 0.1304 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 28.23 _reflns_number_total 2233 _reflns_number_gt 1037 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2233 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1822 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.1407 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3630(3) 0.51113(19) 0.6813(2) 0.0309(6) Uani 1 1 d . . . N3 N 0.2483(3) 0.57304(17) 0.4877(2) 0.0288(6) Uani 1 1 d . . . C1 C 0.4523(5) 0.5041(4) 0.8227(3) 0.0493(9) Uani 1 1 d . . . H1A H 0.381(5) 0.540(3) 0.889(3) 0.075(11) Uiso 1 1 d . . . H1B H 0.578(6) 0.532(3) 0.827(4) 0.097(14) Uiso 1 1 d . . . H1C H 0.462(5) 0.438(3) 0.848(4) 0.068(12) Uiso 1 1 d . . . C2 C 0.3324(3) 0.5971(2) 0.6111(3) 0.0293(7) Uani 1 1 d . . . C3 C 0.1875(5) 0.6448(3) 0.3780(3) 0.0404(8) Uani 1 1 d . . . H3A H 0.286(4) 0.683(2) 0.362(3) 0.050(10) Uiso 1 1 d . . . H3B H 0.142(4) 0.605(2) 0.296(3) 0.047(9) Uiso 1 1 d . . . H3C H 0.111(5) 0.690(3) 0.412(4) 0.076(12) Uiso 1 1 d . . . C4 C 0.2266(4) 0.4701(2) 0.4805(3) 0.0321(7) Uani 1 1 d . . . H4A H 0.172(3) 0.441(2) 0.404(3) 0.030(8) Uiso 1 1 d . . . C5 C 0.2975(4) 0.4313(3) 0.6005(3) 0.0337(7) Uani 1 1 d . . . H5A H 0.311(4) 0.365(2) 0.630(3) 0.039(8) Uiso 1 1 d . . . C6 C 0.3853(5) 0.6992(3) 0.6575(4) 0.0461(9) Uani 1 1 d . . . H6A H 0.375(4) 0.710(3) 0.752(3) 0.071(11) Uiso 1 1 d . . . H6B H 0.291(6) 0.756(4) 0.617(4) 0.117(16) Uiso 1 1 d . . . H6C H 0.489(6) 0.717(3) 0.636(4) 0.096(15) Uiso 1 1 d . . . O1 O 0.4619(3) 0.20583(16) 0.67109(19) 0.0433(6) Uani 1 1 d . . . O2 O 0.5987(3) 0.06064(19) 0.6503(2) 0.0536(7) Uani 1 1 d . . . H1O2 H 0.597(5) 0.001(3) 0.597(4) 0.090(14) Uiso 1 1 d . . . O3 O 0.3825(3) 0.10582(15) 0.49051(19) 0.0423(6) Uani 1 1 d . . . C7 C 0.4750(4) 0.1273(2) 0.6023(3) 0.0332(7) Uani 1 1 d . . . O4 O 0.0864(4) 0.2354(2) 0.4400(2) 0.0507(7) Uani 1 1 d . . . H1O4 H 0.192(5) 0.197(3) 0.449(3) 0.071(12) Uiso 1 1 d . . . H2O4 H 0.060(5) 0.259(3) 0.352(4) 0.102(15) Uiso 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 N1 0.0279(13) 0.0400(16) 0.0245(12) 0.0014(12) 0.0016(9) 0.0013(12) N3 0.0302(13) 0.0307(15) 0.0258(12) 0.0016(12) 0.0047(10) -0.0009(12) C1 0.048(2) 0.067(3) 0.0310(18) 0.001(2) -0.0052(15) 0.012(2) C2 0.0272(15) 0.0362(19) 0.0252(15) -0.0025(14) 0.0058(12) -0.0032(13) C3 0.054(2) 0.040(2) 0.0273(18) 0.0058(17) 0.0058(16) 0.0002(19) C4 0.0361(17) 0.0321(19) 0.0282(17) -0.0063(15) 0.0029(13) -0.0012(14) C5 0.0367(17) 0.0294(19) 0.0353(17) -0.0005(16) 0.0057(13) 0.0056(15) C6 0.055(2) 0.042(2) 0.042(2) -0.0144(18) 0.0080(18) -0.0129(19) O1 0.0478(13) 0.0413(14) 0.0401(12) -0.0083(11) 0.0011(9) 0.0006(11) O2 0.0605(16) 0.0504(15) 0.0450(13) -0.0099(12) -0.0230(11) 0.0217(13) O3 0.0464(13) 0.0417(13) 0.0352(12) 0.0008(10) -0.0155(10) 0.0053(10) C7 0.0341(17) 0.0350(19) 0.0307(16) 0.0092(15) 0.0041(13) -0.0021(14) O4 0.0563(16) 0.0577(17) 0.0382(13) -0.0016(12) 0.0050(11) 0.0184(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.338(3) . ? N1 C5 1.380(4) . ? N1 C1 1.466(4) . ? N3 C2 1.334(3) . ? N3 C4 1.379(4) . ? N3 C3 1.466(4) . ? C1 H1A 0.99(4) . ? C1 H1B 1.01(4) . ? C1 H1C 0.92(4) . ? C2 C6 1.471(4) . ? C3 H3A 0.92(3) . ? C3 H3B 0.98(3) . ? C3 H3C 0.91(4) . ? C4 C5 1.333(4) . ? C4 H4A 0.90(3) . ? C5 H5A 0.93(3) . ? C6 H6A 0.93(3) . ? C6 H6B 1.09(5) . ? C6 H6C 0.85(4) . ? O1 C7 1.245(3) . ? O2 C7 1.334(3) . ? O2 H1O2 0.95(4) . ? O3 C7 1.261(3) . ? O4 H1O4 0.94(4) . ? O4 H2O4 0.91(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 _geom_angle_publ_flag C2 N1 C5 109.5(2) . . ? C2 N1 C1 124.6(3) . . ? C5 N1 C1 125.8(3) . . ? C2 N3 C4 109.1(2) . . ? C2 N3 C3 125.4(3) . . ? C4 N3 C3 125.5(2) . . ? N1 C1 H1A 110.3(19) . . ? N1 C1 H1B 111(2) . . ? H1A C1 H1B 111(3) . . ? N1 C1 H1C 109(2) . . ? H1A C1 H1C 109(3) . . ? H1B C1 H1C 107(3) . . ? N3 C2 N1 107.0(2) . . ? N3 C2 C6 125.8(3) . . ? N1 C2 C6 127.2(3) . . ? N3 C3 H3A 106.3(19) . . ? N3 C3 H3B 107.2(17) . . ? H3A C3 H3B 112(2) . . ? N3 C3 H3C 110(2) . . ? H3A C3 H3C 104(3) . . ? H3B C3 H3C 117(3) . . ? C5 C4 N3 107.7(3) . . ? C5 C4 H4A 131.3(17) . . ? N3 C4 H4A 121.1(17) . . ? C4 C5 N1 106.7(3) . . ? C4 C5 H5A 130.8(18) . . ? N1 C5 H5A 122.5(17) . . ? C2 C6 H6A 113(2) . . ? C2 C6 H6B 112(2) . . ? H6A C6 H6B 98(3) . . ? C2 C6 H6C 114(3) . . ? H6A C6 H6C 111(3) . . ? H6B C6 H6C 107(4) . . ? C7 O2 H1O2 113(2) . . ? O1 C7 O3 125.6(3) . . ? O1 C7 O2 117.2(3) . . ? O3 C7 O2 117.3(3) . . ? H1O4 O4 H2O4 113(3) . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.191 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.053 data_[N,N-diMePyr][HCO3] _database_code_depnum_ccdc_archive 'CCDC 752756' #TrackingRef 'Rogers_New_HCO3_Precursors_11-18-09.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (N,N-diMePyr)(HCO3) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H15 N O3' _chemical_formula_weight 161.20 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 6.6199(6) _cell_length_b 13.9451(12) _cell_length_c 9.2587(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.760(2) _cell_angle_gamma 90.00 _cell_volume 836.78(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3123 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.18 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9709 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details '(SADABS; Shieldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5760 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0161 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 28.20 _reflns_number_total 1967 _reflns_number_gt 1648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+0.1149P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1967 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.33570(14) 0.11515(7) 0.69819(10) 0.0476(2) Uani 1 1 d . . . O2 O 0.32499(12) -0.00864(6) 0.84919(9) 0.0372(2) Uani 1 1 d . . . O3 O 0.55451(12) 0.10922(5) 0.91228(9) 0.0351(2) Uani 1 1 d . . . H1O3 H 0.586(2) 0.0703(11) 0.9913(19) 0.059(4) Uiso 1 1 d . . . N1 N 0.17317(11) 0.09761(5) 0.30326(9) 0.02301(19) Uani 1 1 d . . . C1 C 0.13221(17) 0.11431(8) 0.13926(11) 0.0313(2) Uani 1 1 d . . . H1A H 0.207(2) 0.0631(10) 0.0994(15) 0.039(3) Uiso 1 1 d . . . H1B H -0.013(2) 0.1067(10) 0.1010(16) 0.046(4) Uiso 1 1 d . . . C2 C 0.22141(18) 0.21331(9) 0.12348(13) 0.0375(3) Uani 1 1 d . . . H2A H 0.119(2) 0.2623(11) 0.1221(16) 0.051(4) Uiso 1 1 d . . . H2B H 0.276(2) 0.2136(11) 0.0326(18) 0.053(4) Uiso 1 1 d . . . C3 C 0.39323(17) 0.22733(8) 0.26191(14) 0.0364(3) Uani 1 1 d . . . H3A H 0.526(2) 0.2331(11) 0.2374(16) 0.053(4) Uiso 1 1 d . . . H3B H 0.362(2) 0.2859(11) 0.3180(18) 0.056(4) Uiso 1 1 d . . . C4 C 0.38832(15) 0.13701(7) 0.35327(12) 0.0284(2) Uani 1 1 d . . . H4A H 0.4098(19) 0.1445(9) 0.4575(16) 0.035(3) Uiso 1 1 d . . . H4B H 0.481(2) 0.0869(9) 0.3280(14) 0.035(3) Uiso 1 1 d . . . C5 C 0.02245(16) 0.15284(7) 0.37174(12) 0.0294(2) Uani 1 1 d . . . H5A H 0.0289(19) 0.2198(9) 0.3434(14) 0.035(3) Uiso 1 1 d . . . H5B H -0.112(2) 0.1253(10) 0.3360(15) 0.038(3) Uiso 1 1 d . . . H5C H 0.066(2) 0.1458(9) 0.4772(16) 0.036(3) Uiso 1 1 d . . . C6 C 0.16319(18) -0.00569(7) 0.34380(14) 0.0329(3) Uani 1 1 d . . . H6A H 0.256(2) -0.0415(9) 0.2987(15) 0.039(3) Uiso 1 1 d . . . H6B H 0.025(2) -0.0278(9) 0.3113(14) 0.036(3) Uiso 1 1 d . . . H6C H 0.207(2) -0.0096(10) 0.4515(18) 0.043(4) Uiso 1 1 d . . . C7 C 0.39551(15) 0.07040(7) 0.81409(11) 0.0283(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 0.0472(5) 0.0603(6) 0.0338(5) 0.0175(4) 0.0043(4) 0.0010(4) O2 0.0353(4) 0.0377(4) 0.0343(4) 0.0037(3) -0.0032(3) -0.0104(3) O3 0.0368(4) 0.0299(4) 0.0365(4) 0.0056(3) 0.0023(3) -0.0079(3) N1 0.0207(4) 0.0232(4) 0.0249(4) 0.0000(3) 0.0043(3) 0.0005(3) C1 0.0277(5) 0.0424(6) 0.0233(5) -0.0014(4) 0.0043(4) -0.0015(4) C2 0.0372(6) 0.0427(6) 0.0333(6) 0.0122(5) 0.0092(5) 0.0033(5) C3 0.0308(5) 0.0326(6) 0.0455(7) 0.0076(5) 0.0069(5) -0.0051(4) C4 0.0213(4) 0.0310(5) 0.0313(6) 0.0016(4) 0.0016(4) -0.0033(4) C5 0.0295(5) 0.0282(5) 0.0330(6) -0.0005(4) 0.0123(4) 0.0036(4) C6 0.0307(5) 0.0231(5) 0.0466(7) 0.0028(4) 0.0118(5) 0.0005(4) C7 0.0263(5) 0.0335(5) 0.0261(5) 0.0018(4) 0.0079(4) 0.0030(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.2348(13) . ? O2 C7 1.2650(13) . ? O3 C7 1.3555(13) . ? O3 H1O3 0.900(17) . ? N1 C6 1.4936(12) . ? N1 C5 1.4995(12) . ? N1 C1 1.5052(13) . ? N1 C4 1.5086(12) . ? C1 C2 1.5203(16) . ? C1 H1A 0.984(14) . ? C1 H1B 0.958(15) . ? C2 C3 1.5429(17) . ? C2 H2A 0.960(16) . ? C2 H2B 0.980(17) . ? C3 C4 1.5213(15) . ? C3 H3A 0.955(16) . ? C3 H3B 1.012(16) . ? C4 H4A 0.952(14) . ? C4 H4B 0.988(13) . ? C5 H5A 0.974(13) . ? C5 H5B 0.962(14) . ? C5 H5C 0.965(14) . ? C6 H6A 0.950(14) . ? C6 H6B 0.957(13) . ? C6 H6C 0.982(16) . ? 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 _geom_angle_publ_flag C7 O3 H1O3 109.0(10) . . ? C6 N1 C5 108.77(8) . . ? C6 N1 C1 113.24(8) . . ? C5 N1 C1 110.40(8) . . ? C6 N1 C4 111.19(8) . . ? C5 N1 C4 110.56(8) . . ? C1 N1 C4 102.59(7) . . ? N1 C1 C2 104.11(9) . . ? N1 C1 H1A 105.4(8) . . ? C2 C1 H1A 112.8(8) . . ? N1 C1 H1B 108.5(9) . . ? C2 C1 H1B 116.4(8) . . ? H1A C1 H1B 109.0(11) . . ? C1 C2 C3 105.68(9) . . ? C1 C2 H2A 111.2(9) . . ? C3 C2 H2A 108.6(9) . . ? C1 C2 H2B 107.7(9) . . ? C3 C2 H2B 112.0(9) . . ? H2A C2 H2B 111.5(12) . . ? C4 C3 C2 105.15(9) . . ? C4 C3 H3A 109.0(9) . . ? C2 C3 H3A 111.8(9) . . ? C4 C3 H3B 110.6(9) . . ? C2 C3 H3B 109.5(9) . . ? H3A C3 H3B 110.5(13) . . ? N1 C4 C3 104.88(8) . . ? N1 C4 H4A 106.7(8) . . ? C3 C4 H4A 117.2(7) . . ? N1 C4 H4B 105.2(7) . . ? C3 C4 H4B 111.7(7) . . ? H4A C4 H4B 110.2(11) . . ? N1 C5 H5A 108.0(8) . . ? N1 C5 H5B 107.3(8) . . ? H5A C5 H5B 112.2(11) . . ? N1 C5 H5C 106.8(8) . . ? H5A C5 H5C 110.5(11) . . ? H5B C5 H5C 111.7(11) . . ? N1 C6 H6A 109.3(8) . . ? N1 C6 H6B 108.7(8) . . ? H6A C6 H6B 110.8(11) . . ? N1 C6 H6C 106.9(8) . . ? H6A C6 H6C 109.5(11) . . ? H6B C6 H6C 111.5(11) . . ? O1 C7 O2 126.43(10) . . ? O1 C7 O3 116.66(10) . . ? O2 C7 O3 116.90(9) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.157 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.045