#------------------------------------------------------------------------------ #$Date: 2016-03-21 00:21:50 +0100 (Mon, 21 Mar 2016) $ #$Revision: 178377 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/15/4001550.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_4001550 loop_ _publ_author_name 'Ballabh, Amar' 'Trivedi, Darshak R.' 'Dastidar, Parthasarathi' _publ_section_title ; New Series of Organogelators Derived from a Combinatorial Library of Primary Ammonium Monocarboxylate Salts ; _journal_issue 16 _journal_name_full 'Chemistry of Materials' _journal_page_first 3795 _journal_paper_doi 10.1021/cm0605015 _journal_volume 18 _journal_year 2006 _chemical_formula_sum 'C23 H38 Br N O2' _chemical_formula_weight 440.45 _chemical_name_systematic ; ? ; _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' _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 95.027(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 28.972(4) _cell_length_b 14.2687(17) _cell_length_c 5.7800(7) _cell_measurement_temperature 293(2) _cell_volume 2380.2(5) _computing_cell_refinement 'BRUKER AXS SMART 3' _computing_data_collection 'BRUKER AXS SMART 3' _computing_data_reduction 'BRUKER AXS SMART 3' _computing_molecular_graphics 'PLATON, MERCURY 1.2' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.937 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device_type 'BRUKER SMART CCD AREA DETECTOR' _diffrn_measurement_method PHI-OMEGA _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 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 14222 _diffrn_reflns_theta_full 28.29 _diffrn_reflns_theta_max 28.29 _diffrn_reflns_theta_min 1.59 _diffrn_standards_decay_% '<10 %' _exptl_absorpt_coefficient_mu 1.743 _exptl_absorpt_correction_type SADABS _exptl_crystal_colour COLOURLESS _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_description PLATE _exptl_crystal_F_000 936 _exptl_crystal_size_max 1.22mm _exptl_crystal_size_mid 0.82mm _exptl_crystal_size_min 0.02mm _refine_diff_density_max 0.574 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 5544 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.988 _refine_ls_R_factor_all 0.0925 _refine_ls_R_factor_gt 0.0474 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1015 _refine_ls_wR_factor_ref 0.1167 _reflns_number_gt 3393 _reflns_number_total 5544 _reflns_threshold_expression >2sigma(I) _cod_data_source_file cm0605015si20060301_110327.cif _cod_data_source_block ab0671 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 2(1)/C' _cod_database_code 4001550 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_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 Br1 Br 0.223877(10) 0.34325(2) 1.03217(5) 0.06209(14) Uani 1 1 d . N1 N 0.53648(7) 0.35777(15) 0.9536(4) 0.0530(6) Uani 1 1 d . H1NA H 0.5304 0.3737 0.8052 0.079 Uiso 1 1 calc R H1NB H 0.5156 0.3839 1.0378 0.079 Uiso 1 1 calc R H1NC H 0.5352 0.2957 0.9672 0.079 Uiso 1 1 calc R O1 O 0.51500(6) 0.34330(12) 0.4723(3) 0.0543(5) Uani 1 1 d . O2 O 0.46894(6) 0.42080(15) 0.2117(3) 0.0655(6) Uani 1 1 d . C1 C 0.47679(9) 0.37997(19) 0.4012(5) 0.0460(6) Uani 1 1 d . C2 C 0.43854(9) 0.37142(19) 0.5569(5) 0.0533(7) Uani 1 1 d . H2 H 0.4447 0.3391 0.6960 0.064 Uiso 1 1 calc R C3 C 0.39713(8) 0.40624(17) 0.5111(4) 0.0432(6) Uani 1 1 d . H3 H 0.3925 0.4418 0.3763 0.052 Uiso 1 1 calc R C4 C 0.35677(8) 0.39585(16) 0.6480(4) 0.0395(6) Uani 1 1 d . C5 C 0.35931(9) 0.35248(15) 0.8642(4) 0.0421(6) Uani 1 1 d . H5 H 0.3879 0.3334 0.9337 0.050 Uiso 1 1 calc R C6 C 0.32002(9) 0.33748(15) 0.9766(5) 0.0454(6) Uani 1 1 d . H6 H 0.3221 0.3078 1.1204 0.055 Uiso 1 1 calc R C7 C 0.27769(8) 0.36632(16) 0.8764(5) 0.0421(6) Uani 1 1 d . C8 C 0.27398(9) 0.41048(18) 0.6646(4) 0.0483(6) Uani 1 1 d . H8 H 0.2453 0.4304 0.5980 0.058 Uiso 1 1 calc R C9 C 0.31355(9) 0.42489(17) 0.5515(4) 0.0475(6) Uani 1 1 d . H9 H 0.3111 0.4547 0.4079 0.057 Uiso 1 1 calc R C10 C 0.58313(8) 0.39092(18) 1.0375(4) 0.0453(6) Uani 1 1 d . H10B H 0.5893 0.3744 1.2000 0.054 Uiso 1 1 calc R H10A H 0.5841 0.4587 1.0256 0.054 Uiso 1 1 calc R C11 C 0.62035(9) 0.34955(17) 0.9020(5) 0.0488(7) Uani 1 1 d . H11A H 0.6140 0.3658 0.7393 0.059 Uiso 1 1 calc R H11B H 0.6195 0.2818 0.9146 0.059 Uiso 1 1 calc R C12 C 0.66815(9) 0.38402(18) 0.9872(5) 0.0523(7) Uani 1 1 d . H12B H 0.6745 0.3662 1.1489 0.063 Uiso 1 1 calc R H12A H 0.6683 0.4519 0.9799 0.063 Uiso 1 1 calc R C13 C 0.70692(9) 0.34671(18) 0.8514(6) 0.0586(8) Uani 1 1 d . H13B H 0.7073 0.2788 0.8612 0.070 Uiso 1 1 calc R H13A H 0.7005 0.3636 0.6892 0.070 Uiso 1 1 calc R C14 C 0.75412(10) 0.3837(2) 0.9377(6) 0.0652(8) Uani 1 1 d . H14B H 0.7608 0.3649 1.0984 0.078 Uiso 1 1 calc R H14A H 0.7532 0.4517 0.9338 0.078 Uiso 1 1 calc R C15 C 0.79335(10) 0.3506(2) 0.7998(7) 0.0731(9) Uani 1 1 d . H15A H 0.7942 0.2826 0.8030 0.088 Uiso 1 1 calc R H15B H 0.7868 0.3697 0.6393 0.088 Uiso 1 1 calc R C16 C 0.84068(10) 0.3875(2) 0.8881(6) 0.0747(9) Uani 1 1 d . H16A H 0.8399 0.4555 0.8857 0.090 Uiso 1 1 calc R H16B H 0.8475 0.3679 1.0481 0.090 Uiso 1 1 calc R C17 C 0.87924(10) 0.3545(2) 0.7481(7) 0.0802(11) Uani 1 1 d . H17A H 0.8798 0.2865 0.7506 0.096 Uiso 1 1 calc R H17B H 0.8721 0.3738 0.5881 0.096 Uiso 1 1 calc R C18 C 0.92692(10) 0.3900(2) 0.8304(6) 0.0743(9) Uani 1 1 d . H18B H 0.9347 0.3690 0.9886 0.089 Uiso 1 1 calc R H18A H 0.9265 0.4580 0.8313 0.089 Uiso 1 1 calc R C19 C 0.96408(11) 0.3570(2) 0.6803(7) 0.0806(11) Uani 1 1 d . H19B H 0.9652 0.2891 0.6855 0.097 Uiso 1 1 calc R H19A H 0.9552 0.3751 0.5209 0.097 Uiso 1 1 calc R C20 C 1.01202(10) 0.3944(2) 0.7487(6) 0.0788(10) Uani 1 1 d . H20B H 1.0216 0.3746 0.9061 0.095 Uiso 1 1 calc R H20A H 1.0109 0.4624 0.7476 0.095 Uiso 1 1 calc R C21 C 1.04811(11) 0.3619(2) 0.5890(8) 0.0855(11) Uani 1 1 d . H21B H 1.0498 0.2940 0.5952 0.103 Uiso 1 1 calc R H21A H 1.0375 0.3792 0.4309 0.103 Uiso 1 1 calc R C22 C 1.09552(12) 0.4000(3) 0.6434(7) 0.1001(12) Uani 1 1 d . H22B H 1.1067 0.3815 0.7998 0.120 Uiso 1 1 calc R H22A H 1.0941 0.4679 0.6394 0.120 Uiso 1 1 calc R C23 C 1.12986(13) 0.3668(3) 0.4758(8) 0.1182(16) Uani 1 1 d . H23A H 1.1352 0.3008 0.4966 0.177 Uiso 1 1 calc R H23B H 1.1586 0.4001 0.5061 0.177 Uiso 1 1 calc R H23C H 1.1174 0.3786 0.3191 0.177 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 Br1 0.0521(2) 0.0677(2) 0.0704(2) -0.00121(15) 0.02718(15) -0.00811(14) N1 0.0382(12) 0.0836(16) 0.0378(13) -0.0006(11) 0.0067(10) 0.0001(11) O1 0.0444(11) 0.0772(13) 0.0420(11) 0.0076(9) 0.0080(8) 0.0126(9) O2 0.0502(12) 0.1043(16) 0.0437(12) 0.0232(11) 0.0130(9) 0.0233(10) C1 0.0408(15) 0.0597(16) 0.0383(16) -0.0016(13) 0.0076(12) 0.0025(12) C2 0.0456(16) 0.0762(19) 0.0387(16) 0.0105(13) 0.0079(12) 0.0050(14) C3 0.0449(15) 0.0476(15) 0.0380(14) 0.0010(12) 0.0084(11) -0.0009(12) C4 0.0413(14) 0.0400(13) 0.0376(14) -0.0049(11) 0.0061(11) -0.0025(11) C5 0.0405(14) 0.0434(14) 0.0423(15) -0.0029(11) 0.0032(11) 0.0062(11) C6 0.0535(16) 0.0424(14) 0.0416(15) 0.0031(12) 0.0112(12) 0.0010(12) C7 0.0397(14) 0.0423(14) 0.0461(15) -0.0065(11) 0.0142(12) -0.0046(10) C8 0.0377(14) 0.0619(17) 0.0457(16) -0.0023(13) 0.0061(12) 0.0032(12) C9 0.0470(16) 0.0581(16) 0.0374(15) 0.0029(12) 0.0039(12) 0.0030(12) C10 0.0391(14) 0.0506(15) 0.0465(16) 0.0023(13) 0.0054(12) 0.0003(11) C11 0.0422(15) 0.0537(16) 0.0513(17) -0.0004(13) 0.0091(12) -0.0012(12) C12 0.0451(16) 0.0498(15) 0.0631(19) -0.0007(14) 0.0115(13) 0.0006(12) C13 0.0470(16) 0.0527(16) 0.078(2) -0.0067(15) 0.0190(15) -0.0036(13) C14 0.0473(17) 0.0595(17) 0.090(2) -0.0085(17) 0.0161(16) -0.0006(14) C15 0.0482(18) 0.071(2) 0.103(3) -0.0058(18) 0.0244(17) -0.0032(14) C16 0.0475(18) 0.072(2) 0.108(3) -0.007(2) 0.0231(18) -0.0010(15) C17 0.0468(19) 0.088(2) 0.109(3) -0.0120(19) 0.0262(19) -0.0044(15) C18 0.0492(19) 0.079(2) 0.097(3) -0.006(2) 0.0190(18) -0.0011(16) C19 0.0503(19) 0.092(3) 0.102(3) -0.007(2) 0.0212(19) 0.0023(16) C20 0.0469(19) 0.091(2) 0.100(3) -0.001(2) 0.0182(18) 0.0034(17) C21 0.052(2) 0.097(3) 0.111(3) -0.001(2) 0.023(2) 0.0067(17) C22 0.052(2) 0.141(3) 0.109(3) 0.000(3) 0.016(2) 0.004(2) C23 0.057(2) 0.174(4) 0.129(4) 0.019(3) 0.034(2) 0.022(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' Br Br -0.2901 2.4595 '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 C10 N1 H1NA 109.5 . . C10 N1 H1NB 109.5 . . H1NA N1 H1NB 109.5 . . C10 N1 H1NC 109.5 . . H1NA N1 H1NC 109.5 . . H1NB N1 H1NC 109.5 . . O1 O1 C1 0(10) 1 . O2 C1 O1 124.7(2) . 1 O2 C1 O1 124.7(2) . . O1 C1 O1 0.00(16) 1 . O2 C1 C2 118.8(2) . . O1 C1 C2 116.5(2) 1 . O1 C1 C2 116.5(2) . . C3 C2 C1 124.4(3) . . C3 C2 H2 117.8 . . C1 C2 H2 117.8 . . C2 C3 C4 127.7(2) . . C2 C3 H3 116.2 . . C4 C3 H3 116.2 . . C9 C4 C5 117.9(2) . . C9 C4 C3 118.9(2) . . C5 C4 C3 123.0(2) . . C6 C5 C4 120.9(2) . . C6 C5 H5 119.6 . . C4 C5 H5 119.6 . . C7 C6 C5 120.0(2) . . C7 C6 H6 120.0 . . C5 C6 H6 120.0 . . C8 C7 C6 120.7(2) . . C8 C7 Br1 120.00(19) . . C6 C7 Br1 119.3(2) . . C7 C8 C9 119.1(2) . . C7 C8 H8 120.5 . . C9 C8 H8 120.5 . . C8 C9 C4 121.4(2) . . C8 C9 H9 119.3 . . C4 C9 H9 119.3 . . N1 C10 C11 112.4(2) . . N1 C10 H10B 109.1 . . C11 C10 H10B 109.1 . . N1 C10 H10A 109.1 . . C11 C10 H10A 109.1 . . H10B C10 H10A 107.9 . . C10 C11 C12 112.3(2) . . C10 C11 H11A 109.1 . . C12 C11 H11A 109.1 . . C10 C11 H11B 109.1 . . C12 C11 H11B 109.1 . . H11A C11 H11B 107.9 . . C11 C12 C13 114.5(2) . . C11 C12 H12B 108.6 . . C13 C12 H12B 108.6 . . C11 C12 H12A 108.6 . . C13 C12 H12A 108.6 . . H12B C12 H12A 107.6 . . C14 C13 C12 113.3(2) . . C14 C13 H13B 108.9 . . C12 C13 H13B 108.9 . . C14 C13 H13A 108.9 . . C12 C13 H13A 108.9 . . H13B C13 H13A 107.7 . . C13 C14 C15 114.5(3) . . C13 C14 H14B 108.6 . . C15 C14 H14B 108.6 . . C13 C14 H14A 108.6 . . C15 C14 H14A 108.6 . . H14B C14 H14A 107.6 . . C16 C15 C14 114.3(3) . . C16 C15 H15A 108.7 . . C14 C15 H15A 108.7 . . C16 C15 H15B 108.7 . . C14 C15 H15B 108.7 . . H15A C15 H15B 107.6 . . C17 C16 C15 113.6(3) . . C17 C16 H16A 108.8 . . C15 C16 H16A 108.8 . . C17 C16 H16B 108.8 . . C15 C16 H16B 108.8 . . H16A C16 H16B 107.7 . . C18 C17 C16 115.2(3) . . C18 C17 H17A 108.5 . . C16 C17 H17A 108.5 . . C18 C17 H17B 108.5 . . C16 C17 H17B 108.5 . . H17A C17 H17B 107.5 . . C17 C18 C19 113.1(3) . . C17 C18 H18B 109.0 . . C19 C18 H18B 109.0 . . C17 C18 H18A 109.0 . . C19 C18 H18A 109.0 . . H18B C18 H18A 107.8 . . C20 C19 C18 115.1(3) . . C20 C19 H19B 108.5 . . C18 C19 H19B 108.5 . . C20 C19 H19A 108.5 . . C18 C19 H19A 108.5 . . H19B C19 H19A 107.5 . . C19 C20 C21 113.4(3) . . C19 C20 H20B 108.9 . . C21 C20 H20B 108.9 . . C19 C20 H20A 108.9 . . C21 C20 H20A 108.9 . . H20B C20 H20A 107.7 . . C22 C21 C20 115.5(3) . . C22 C21 H21B 108.4 . . C20 C21 H21B 108.4 . . C22 C21 H21A 108.4 . . C20 C21 H21A 108.4 . . H21B C21 H21A 107.5 . . C21 C22 C23 113.3(4) . . C21 C22 H22B 108.9 . . C23 C22 H22B 108.9 . . C21 C22 H22A 108.9 . . C23 C22 H22A 108.9 . . H22B C22 H22A 107.7 . . C22 C23 H23A 109.5 . . C22 C23 H23B 109.5 . . H23A C23 H23B 109.5 . . C22 C23 H23C 109.5 . . H23A C23 H23C 109.5 . . H23B C23 H23C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Br1 C7 1.896(2) . N1 C10 1.473(3) . N1 H1NA 0.8900 . N1 H1NB 0.8900 . N1 H1NC 0.8900 . O1 O1 0.000(4) 1 O1 C1 1.260(3) . O2 C1 1.244(3) . C1 O1 1.260(3) 1 C1 C2 1.493(3) . C2 C3 1.304(3) . C2 H2 0.9300 . C3 C4 1.475(3) . C3 H3 0.9300 . C4 C9 1.389(3) . C4 C5 1.391(3) . C5 C6 1.376(3) . C5 H5 0.9300 . C6 C7 1.373(4) . C6 H6 0.9300 . C7 C8 1.372(3) . C8 C9 1.384(3) . C8 H8 0.9300 . C9 H9 0.9300 . C10 C11 1.507(3) . C10 H10B 0.9700 . C10 H10A 0.9700 . C11 C12 1.511(4) . C11 H11A 0.9700 . C11 H11B 0.9700 . C12 C13 1.522(3) . C12 H12B 0.9700 . C12 H12A 0.9700 . C13 C14 1.509(4) . C13 H13B 0.9700 . C13 H13A 0.9700 . C14 C15 1.520(4) . C14 H14B 0.9700 . C14 H14A 0.9700 . C15 C16 1.515(4) . C15 H15A 0.9700 . C15 H15B 0.9700 . C16 C17 1.511(4) . C16 H16A 0.9700 . C16 H16B 0.9700 . C17 C18 1.509(4) . C17 H17A 0.9700 . C17 H17B 0.9700 . C18 C19 1.515(4) . C18 H18B 0.9700 . C18 H18A 0.9700 . C19 C20 1.508(4) . C19 H19B 0.9700 . C19 H19A 0.9700 . C20 C21 1.526(4) . C20 H20B 0.9700 . C20 H20A 0.9700 . C21 C22 1.485(5) . C21 H21B 0.9700 . C21 H21A 0.9700 . C22 C23 1.524(5) . C22 H22B 0.9700 . C22 H22A 0.9700 . C23 H23A 0.9600 . C23 H23B 0.9600 . C23 H23C 0.9600 . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1NA O1 0.89 1.98 2.805(3) 152.5 1 N1 H1NB O2 0.89 1.83 2.716(3) 171.8 1_556 N1 H1NB O1 0.89 2.58 3.122(3) 120.1 1_556 N1 H1NC O1 0.89 2.07 2.940(3) 165.6 4_566