#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/37/2013792.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013792 loop_ _publ_author_name 'Muir, Kenneth W.' 'Morris, David G.' 'Chii, Cindy Ong Woei' _publ_section_title ; 4-Chloro-N-(trimethylammonio)benzamide chloride monohydrate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o125 _journal_page_last o126 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C10 H14 Cl N2 O 1+, Cl 1-, H2 O' _chemical_formula_moiety 'C10 H14 Cl N2 O 1+, Cl 1-, H2 O' _chemical_formula_sum 'C10 H16 Cl2 N2 O2' _chemical_formula_weight 267.15 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 98.2790(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.0302(2) _cell_length_b 9.9377(2) _cell_length_c 17.8571(5) _cell_measurement_reflns_used 2648 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 0.998 _cell_volume 1234.57(6) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Nonius BV, 2000)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor 1997) and Scalepack' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD rotation images, thick slice' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 10868 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 2.35 _exptl_absorpt_coefficient_mu 0.514 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.35 _refine_diff_density_min -0.29 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2806 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_gt 0.0295 _refine_ls_shift/su_max 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.026P)^2^+0.67P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0732 _reflns_number_gt 2465 _reflns_number_total 2806 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1295.cif _[local]_cod_data_source_block IIa _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2013792 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 C1 0.6093(2) 1.04442(15) 0.12359(8) 0.0160(3) Uani d . 1 . . C H1A 0.5901 1.0478 0.0682 0.024 Uiso calc R 1 . . H H1B 0.6131 1.1362 0.1438 0.024 Uiso calc R 1 . . H H1C 0.5030 0.9949 0.1408 0.024 Uiso calc R 1 . . H C2 0.9659(2) 1.04958(15) 0.12910(9) 0.0169(3) Uani d . 1 . . C H2A 1.084 0.9986 0.1454 0.025 Uiso calc R 1 . . H H2B 0.9751 1.1382 0.1535 0.025 Uiso calc R 1 . . H H2C 0.9489 1.0609 0.074 0.025 Uiso calc R 1 . . H C3 0.8211(2) 0.96659(15) 0.23638(8) 0.0160(3) Uani d . 1 . . C H3A 0.7127 0.9174 0.2521 0.024 Uiso calc R 1 . . H H3B 0.8254 1.0578 0.2574 0.024 Uiso calc R 1 . . H H3C 0.9411 0.9196 0.2549 0.024 Uiso calc R 1 . . H C4 0.77291(18) 0.81360(14) 0.04700(8) 0.0122(3) Uani d . 1 . . C C5 0.76383(18) 0.66760(14) 0.02648(8) 0.0123(3) Uani d . 1 . . C C6 0.83602(19) 0.56595(14) 0.07634(8) 0.0133(3) Uani d . 1 . . C H6 0.8938 0.5883 0.1262 0.016 Uiso calc R 1 . . H C7 0.82417(19) 0.43234(14) 0.05375(8) 0.0140(3) Uani d . 1 . . C H7 0.8735 0.3629 0.0876 0.017 Uiso calc R 1 . . H C8 0.73898(19) 0.40194(14) -0.01925(8) 0.0138(3) Uani d . 1 . . C C9 0.66555(19) 0.50115(15) -0.06997(8) 0.0148(3) Uani d . 1 . . C H9 0.6067 0.4782 -0.1196 0.018 Uiso calc R 1 . . H C10 0.67965(19) 0.63441(14) -0.04700(8) 0.0138(3) Uani d . 1 . . C H10 0.6319 0.7036 -0.0813 0.017 Uiso calc R 1 . . H Cl1 0.32457(5) 0.84579(3) 0.262707(19) 0.01625(10) Uani d . 1 . . Cl Cl2 0.72520(5) 0.23452(3) -0.04804(2) 0.01815(10) Uani d . 1 . . Cl N1 0.79562(17) 0.83738(12) 0.12357(7) 0.0126(2) Uani d . 1 . . N N2 0.79629(16) 0.97424(11) 0.15125(6) 0.0124(2) Uani d . 1 . . N O1 0.76408(14) 0.90229(10) -0.00071(6) 0.0155(2) Uani d . 1 . . O O1W 0.67018(16) 0.66488(12) 0.22895(6) 0.0202(2) Uani d . 1 . . O H1 0.758(3) 0.7808(19) 0.1548(10) 0.023(5) Uiso d . 1 . . H H1W 0.558(3) 0.696(2) 0.2388(13) 0.047(6) Uiso d . 1 . . H H2W 0.664(3) 0.587(3) 0.2300(14) 0.056(8) Uiso d . 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 C1 0.0146(6) 0.0132(7) 0.0195(7) 0.0039(5) -0.0006(5) -0.0017(6) C2 0.0155(7) 0.0140(7) 0.0210(7) -0.0044(5) 0.0019(5) 0.0007(6) C3 0.0199(7) 0.0149(7) 0.0128(7) 0.0000(6) 0.0006(5) -0.0020(6) C4 0.0090(6) 0.0126(7) 0.0151(6) 0.0011(5) 0.0021(5) -0.0001(6) C5 0.0097(6) 0.0130(7) 0.0147(7) 0.0008(5) 0.0034(5) -0.0012(6) C6 0.0132(6) 0.0138(7) 0.0127(6) 0.0013(5) 0.0017(5) -0.0008(6) C7 0.0141(6) 0.0128(7) 0.0155(7) 0.0013(5) 0.0030(5) 0.0017(6) C8 0.0128(6) 0.0108(7) 0.0186(7) -0.0013(5) 0.0049(5) -0.0040(6) C9 0.0124(6) 0.0179(7) 0.0141(7) 0.0001(5) 0.0014(5) -0.0027(6) C10 0.0125(6) 0.0147(7) 0.0141(7) 0.0026(5) 0.0016(5) 0.0013(6) Cl1 0.01776(17) 0.01201(17) 0.01916(18) 0.00229(12) 0.00327(12) 0.00137(13) Cl2 0.01974(18) 0.01195(17) 0.02273(19) -0.00116(13) 0.00290(13) -0.00496(14) N1 0.0159(6) 0.0073(6) 0.0146(6) -0.0004(4) 0.0027(4) -0.0001(5) N2 0.0135(5) 0.0088(5) 0.0145(6) 0.0001(4) 0.0010(4) -0.0011(5) O1 0.0176(5) 0.0128(5) 0.0161(5) 0.0006(4) 0.0021(4) 0.0026(4) O1W 0.0240(6) 0.0121(6) 0.0263(6) 0.0013(4) 0.0099(4) 0.0031(5) 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 C1 N2 . 1.5072(17) ? C1 H1A . 0.98 ? C1 H1B . 0.98 ? C1 H1C . 0.98 ? C2 N2 . 1.5084(17) ? C2 H2A . 0.98 ? C2 H2B . 0.98 ? C2 H2C . 0.98 ? C3 N2 . 1.5069(17) ? C3 H3A . 0.98 ? C3 H3B . 0.98 ? C3 H3C . 0.98 ? C4 O1 . 1.2212(17) yes C4 N1 . 1.3739(18) yes C4 C5 . 1.4956(19) yes C5 C6 . 1.3931(19) ? C5 C10 . 1.3989(19) ? C6 C7 . 1.387(2) ? C6 H6 . 0.95 ? C7 C8 . 1.3872(19) ? C7 H7 . 0.95 ? C8 C9 . 1.387(2) ? C8 Cl2 . 1.7399(14) ? C9 C10 . 1.386(2) ? C9 H9 . 0.95 ? C10 H10 . 0.95 ? N1 N2 . 1.4469(16) yes N1 H1 . 0.860(19) ? O1W H1W . 0.89(2) ? O1W H2W . 0.78(3) ? 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 '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_publ_flag N2 C1 H1A 109.5 ? N2 C1 H1B 109.5 ? H1A C1 H1B 109.5 ? N2 C1 H1C 109.5 ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? N2 C2 H2A 109.5 ? N2 C2 H2B 109.5 ? H2A C2 H2B 109.5 ? N2 C2 H2C 109.5 ? H2A C2 H2C 109.5 ? H2B C2 H2C 109.5 ? N2 C3 H3A 109.5 ? N2 C3 H3B 109.5 ? H3A C3 H3B 109.5 ? N2 C3 H3C 109.5 ? H3A C3 H3C 109.5 ? H3B C3 H3C 109.5 ? O1 C4 N1 123.85(13) yes O1 C4 C5 122.22(12) yes N1 C4 C5 113.92(12) yes C6 C5 C10 119.64(13) ? C6 C5 C4 123.24(12) ? C10 C5 C4 117.13(12) ? C7 C6 C5 120.48(13) ? C7 C6 H6 119.8 ? C5 C6 H6 119.8 ? C6 C7 C8 118.79(13) ? C6 C7 H7 120.6 ? C8 C7 H7 120.6 ? C9 C8 C7 121.90(13) ? C9 C8 Cl2 119.15(11) ? C7 C8 Cl2 118.94(11) ? C10 C9 C8 118.81(13) ? C10 C9 H9 120.6 ? C8 C9 H9 120.6 ? C9 C10 C5 120.37(13) ? C9 C10 H10 119.8 ? C5 C10 H10 119.8 ? C4 N1 N2 119.73(11) yes C4 N1 H1 122.0(12) yes N2 N1 H1 112.3(12) yes N1 N2 C3 106.94(10) ? N1 N2 C1 111.30(10) ? C3 N2 C1 108.82(11) ? N1 N2 C2 109.92(10) ? C3 N2 C2 107.98(10) ? C1 N2 C2 111.69(11) ? H1W O1W H2W 107(2) ? 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 N1 H1 O1W . 0.86(2) 1.92(2) 2.7813(17) 176(2) O1W H1W Cl1 . 0.89(2) 2.30(2) 3.1497(12) 160(2) O1W H2W Cl1 2_645 0.78(3) 2.40(3) 3.1745(12) 175(2) 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_publ_flag O1 C4 C5 C6 157.62(13) ? N1 C4 C5 C6 -21.17(18) yes O1 C4 C5 C10 -21.75(19) ? N1 C4 C5 C10 159.46(12) yes C10 C5 C6 C7 -0.3(2) ? C4 C5 C6 C7 -179.64(12) ? C5 C6 C7 C8 -0.1(2) ? C6 C7 C8 C9 -0.1(2) ? C6 C7 C8 Cl2 179.59(10) ? C7 C8 C9 C10 0.6(2) ? Cl2 C8 C9 C10 -179.04(10) ? C8 C9 C10 C5 -1.0(2) ? C6 C5 C10 C9 0.9(2) ? C4 C5 C10 C9 -179.76(12) ? O1 C4 N1 N2 4.53(19) ? C5 C4 N1 N2 -176.70(11) yes C4 N1 N2 C3 179.31(11) yes C4 N1 N2 C1 60.57(15) ? C4 N1 N2 C2 -63.71(14) ? _cod_database_fobs_code 2013792