data_2203233 loop_ _publ_author_name 'Rademeyer, Melanie' _publ_section_title ; Benzyl(1,1-dimethyl-3-oxobutyl)ammonium iodide ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o267 _journal_page_last o268 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C13 H20 N O 1+, I 1-' _chemical_formula_moiety 'C13 H20 N O 1+, I 1-' _chemical_formula_sum 'C13 H20 I N O' _chemical_formula_weight 333.20 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ; benzyl(1,1-dimethyl-3-oxobutyl)ammonium iodide ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 96.04(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.008(4) _cell_length_b 18.046(3) _cell_length_c 9.8377(16) _cell_measurement_reflns_used 54 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 31 _cell_measurement_theta_min 2 _cell_volume 1413.8(8) _computing_cell_refinement 'CrysAlis CCD' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2003)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2003)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999) and PLATON (Spek, 2000)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.92 _diffrn_measurement_device_type 'Oxford Excalibur2' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 12724 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 31.9 _diffrn_reflns_theta_min 4.3 _diffrn_standards_decay_% <2 _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_number n/a _exptl_absorpt_coefficient_mu 2.248 _exptl_absorpt_correction_T_max 0.508 _exptl_absorpt_correction_T_min 0.429 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Blessing, 1995)' _exptl_crystal_colour 'light brown' _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.80 _refine_diff_density_min -0.92 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 146 _refine_ls_number_reflns 4475 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.07 _refine_ls_R_factor_all 0.028 _refine_ls_R_factor_gt 0.025 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0277P)^2^+0.8647P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.057 _refine_ls_wR_factor_ref 0.059 _reflns_number_gt 4097 _reflns_number_total 4475 _reflns_threshold_expression I>2\s(I) 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_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 -0.17571(16) 0.02992(7) -0.01389(13) 0.0239(3) Uani d . 1 . . O C9 0.1020(2) 0.16747(10) 0.00336(19) 0.0237(3) Uani d . 1 . . C H9A 0.0808 0.1275 -0.0606 0.036 Uiso calc R 1 . . H H9B 0.2184 0.1673 0.0388 0.036 Uiso calc R 1 . . H H9C 0.0752 0.2137 -0.0419 0.036 Uiso calc R 1 . . H C12 -0.2587(2) 0.08671(10) -0.01157(16) 0.0190(3) Uani d . 1 . . C C11 -0.1946(2) 0.15445(9) 0.06833(17) 0.0187(3) Uani d . 1 . . C H11A -0.2582 0.1592 0.1465 0.022 Uiso calc R 1 . . H H11B -0.2201 0.1975 0.0109 0.022 Uiso calc R 1 . . H C10 0.0234(2) 0.22033(10) 0.22506(19) 0.0227(3) Uani d . 1 . . C H10A -0.0462 0.2130 0.2976 0.034 Uiso calc R 1 . . H H10B -0.0039 0.2669 0.1810 0.034 Uiso calc R 1 . . H H10C 0.1393 0.2205 0.2619 0.034 Uiso calc R 1 . . H C13 -0.4340(2) 0.09077(12) -0.0820(2) 0.0273(4) Uani d . 1 . . C H13A -0.4553 0.0482 -0.1396 0.041 Uiso calc R 1 . . H H13B -0.4461 0.1349 -0.1366 0.041 Uiso calc R 1 . . H H13C -0.5127 0.0918 -0.0148 0.041 Uiso calc R 1 . . H C8 -0.0068(2) 0.15768(9) 0.12112(17) 0.0177(3) Uani d . 1 . . C I 0.467662(13) 0.119156(6) 0.331194(12) 0.02305(4) Uani d . 1 . . I C1 -0.0177(2) -0.02056(9) 0.33354(15) 0.0164(3) Uani d . 1 . . C C2 -0.1636(2) -0.06309(11) 0.33290(18) 0.0231(3) Uani d . 1 . . C H2 -0.2684 -0.0404 0.3207 0.028 Uiso calc R 1 . . H N1 0.05079(17) 0.08496(8) 0.19013(13) 0.0159(2) Uani d . 1 . . N H0A 0.0343 0.0485 0.1277 0.019 Uiso calc R 1 . . H H0B 0.1621 0.0881 0.2142 0.019 Uiso calc R 1 . . H C6 0.1396(2) -0.05532(10) 0.35569(17) 0.0197(3) Uani d . 1 . . C H6 0.2372 -0.0272 0.3594 0.024 Uiso calc R 1 . . H C7 -0.0312(2) 0.06201(9) 0.31432(16) 0.0181(3) Uani d . 1 . . C H7A 0.0232 0.0869 0.3945 0.022 Uiso calc R 1 . . H H7B -0.1485 0.0765 0.3034 0.022 Uiso calc R 1 . . H C5 0.1496(3) -0.13187(10) 0.37209(19) 0.0241(3) Uani d . 1 . . C H5 0.2540 -0.1548 0.3857 0.029 Uiso calc R 1 . . H C4 0.0040(3) -0.17409(10) 0.36814(19) 0.0268(4) Uani d . 1 . . C H4 0.0110 -0.2253 0.3772 0.032 Uiso calc R 1 . . H C3 -0.1516(3) -0.13983(11) 0.3507(2) 0.0289(4) Uani d . 1 . . C H3 -0.2487 -0.1681 0.3509 0.035 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0225(6) 0.0244(6) 0.0238(6) 0.0058(5) -0.0012(5) -0.0057(5) C9 0.0240(8) 0.0245(8) 0.0237(8) 0.0018(7) 0.0073(6) 0.0068(6) C12 0.0199(7) 0.0224(8) 0.0148(7) 0.0007(6) 0.0017(5) 0.0008(6) C11 0.0179(7) 0.0175(7) 0.0206(7) 0.0037(5) 0.0017(6) 0.0007(6) C10 0.0223(8) 0.0175(8) 0.0279(8) 0.0018(6) 0.0003(6) -0.0024(6) C13 0.0204(8) 0.0279(9) 0.0320(9) 0.0025(7) -0.0047(7) -0.0010(7) C8 0.0177(7) 0.0156(7) 0.0203(7) -0.0005(5) 0.0038(6) -0.0005(5) I 0.01546(6) 0.02669(7) 0.02676(7) -0.00194(4) 0.00113(4) 0.00107(4) C1 0.0198(7) 0.0167(7) 0.0130(6) 0.0002(5) 0.0031(5) 0.0004(5) C2 0.0194(7) 0.0266(9) 0.0227(8) -0.0034(6) -0.0011(6) 0.0008(6) N1 0.0175(6) 0.0153(6) 0.0147(6) 0.0027(5) 0.0013(5) 0.0014(4) C6 0.0185(7) 0.0201(8) 0.0211(7) 0.0000(6) 0.0053(6) 0.0020(6) C7 0.0214(7) 0.0183(7) 0.0153(7) 0.0016(6) 0.0047(6) 0.0012(5) C5 0.0290(9) 0.0217(8) 0.0222(8) 0.0054(7) 0.0058(7) 0.0006(6) C4 0.0424(11) 0.0172(8) 0.0208(8) -0.0022(7) 0.0034(7) -0.0015(6) C3 0.0328(10) 0.0241(9) 0.0293(9) -0.0117(7) 0.0009(7) 0.0007(7) 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' I I -0.4742 1.8119 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C8 C9 H9A . . 109.5 ? C8 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? C8 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? O1 C12 C13 . . 121.08(16) ? O1 C12 C11 . . 122.06(15) ? C13 C12 C11 . . 116.77(15) ? C12 C11 C8 . . 118.16(14) ? C12 C11 H11A . . 107.8 ? C8 C11 H11A . . 107.8 ? C12 C11 H11B . . 107.8 ? C8 C11 H11B . . 107.8 ? H11A C11 H11B . . 107.1 ? C8 C10 H10A . . 109.5 ? C8 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C8 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? C12 C13 H13A . . 109.5 ? C12 C13 H13B . . 109.5 ? H13A C13 H13B . . 109.5 ? C12 C13 H13C . . 109.5 ? H13A C13 H13C . . 109.5 ? H13B C13 H13C . . 109.5 ? N1 C8 C10 . . 108.64(14) ? N1 C8 C9 . . 105.44(13) ? C10 C8 C9 . . 111.00(14) ? N1 C8 C11 . . 110.88(13) ? C10 C8 C11 . . 109.53(14) ? C9 C8 C11 . . 111.26(15) ? C2 C1 C6 . . 119.44(16) ? C2 C1 C7 . . 119.65(15) ? C6 C1 C7 . . 120.89(15) ? C1 C2 C3 . . 119.79(17) ? C1 C2 H2 . . 120.1 ? C3 C2 H2 . . 120.1 ? C7 N1 C8 . . 117.43(12) ? C7 N1 H0A . . 107.9 ? C8 N1 H0A . . 107.9 ? C7 N1 H0B . . 107.9 ? C8 N1 H0B . . 107.9 ? H0A N1 H0B . . 107.2 ? C5 C6 C1 . . 120.10(16) ? C5 C6 H6 . . 119.9 ? C1 C6 H6 . . 119.9 ? C1 C7 N1 . . 110.07(13) ? C1 C7 H7A . . 109.6 ? N1 C7 H7A . . 109.6 ? C1 C7 H7B . . 109.6 ? N1 C7 H7B . . 109.6 ? H7A C7 H7B . . 108.2 ? C4 C5 C6 . . 120.17(18) ? C4 C5 H5 . . 119.9 ? C6 C5 H5 . . 119.9 ? C3 C4 C5 . . 119.98(17) ? C3 C4 H4 . . 120.0 ? C5 C4 H4 . . 120.0 ? C4 C3 C2 . . 120.47(18) ? C4 C3 H3 . . 119.8 ? C2 C3 H3 . . 119.8 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C12 . 1.223(2) ? C9 C8 . 1.532(2) ? C9 H9A . 0.9600 ? C9 H9B . 0.9600 ? C9 H9C . 0.9600 ? C12 C13 . 1.500(3) ? C12 C11 . 1.514(2) ? C11 C8 . 1.539(2) ? C11 H11A . 0.9700 ? C11 H11B . 0.9700 ? C10 C8 . 1.527(2) ? C10 H10A . 0.9600 ? C10 H10B . 0.9600 ? C10 H10C . 0.9600 ? C13 H13A . 0.9600 ? C13 H13B . 0.9600 ? C13 H13C . 0.9600 ? C8 N1 . 1.526(2) ? C1 C2 . 1.397(2) ? C1 C6 . 1.403(2) ? C1 C7 . 1.504(2) ? C2 C3 . 1.398(3) ? C2 H2 . 0.9300 ? N1 C7 . 1.505(2) ? N1 H0A . 0.9000 ? N1 H0B . 0.9000 ? C6 C5 . 1.392(2) ? C6 H6 . 0.9300 ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C5 C4 . 1.390(3) ? C5 H5 . 0.9300 ? C4 C3 . 1.385(3) ? C4 H4 . 0.9300 ? C3 H3 . 0.9300 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H0A O1 . 0.90 2.09 2.746(2) 128 yes N1 H0A O1 3 0.90 2.19 2.9444(19) 141 yes N1 H0B I . 0.90 2.65 3.532(2) 166 yes