#------------------------------------------------------------------------------ #$Date: 2014-04-30 07:46:05 +0300 (Wed, 30 Apr 2014) $ #$Revision: 112295 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/21/54/7215481.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_7215481 loop_ _publ_author_name 'Dastidar, P.' 'ADALDER, TAPAS KUMAR' _publ_section_title ; The role of secondary ammonium cations in controlling the conformation of C3-symmetric acid moieties and its implication towards the design of supramocular capsules ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/c3ce42655f _journal_year 2014 _chemical_formula_moiety 'C15 H17 O6, C6 H16 N' _chemical_formula_sum 'C21 H33 N O6' _chemical_formula_weight 379.36 _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 112.740(13) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.566(10) _cell_length_b 9.991(7) _cell_length_c 17.129(11) _cell_measurement_temperature 296(2) _cell_volume 2299(3) _computing_cell_refinement 'BRUKER APEX II' _computing_data_collection 'BRUKER APEX II' _computing_data_reduction 'BRUKER APEX II' _computing_molecular_graphics 'MERCURY 2.3, PLATON' _computing_publication_material 'MERCURY 2.3, PLATON' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'BRUKER CCD AREA DETECTOR' _diffrn_measurement_method 'PHI-OMEGA SCAN' _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 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0601 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 10415 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.41 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_T_max 0.9839 _exptl_absorpt_correction_T_min 0.9753 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour COLOURLESS _exptl_crystal_density_diffrn 1.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_description BOLOCK _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.391 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.065 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 4035 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.016 _refine_ls_R_factor_all 0.1429 _refine_ls_R_factor_gt 0.0866 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1513P)^2^+0.3672P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2308 _refine_ls_wR_factor_ref 0.2754 _reflns_number_gt 2223 _reflns_number_total 4035 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c3ce42655f2.cif _[local]_cod_data_source_block iacs_ta _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to 'multi-scan' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius ; _cod_database_code 7215481 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 _atom_site_disorder_assembly _atom_site_disorder_group C17A C -0.0189(11) 0.8090(16) 0.3502(10) 0.118(4) Uiso 0.43 1 d P A 1 C20A C 0.1274(10) 0.8251(14) 0.1761(8) 0.122(4) Uiso 0.57 1 d P A 1 C21A C 0.1073(10) 0.8221(15) 0.0838(9) 0.137(4) Uiso 0.58 1 d P A 1 N1A N 0.1173(4) 0.9450(5) 0.3024(3) 0.0600(14) Uiso 0.60 1 d P A 1 C17B C 0.0147(7) 0.8994(11) 0.3853(7) 0.102(3) Uiso 0.57 1 d P A 2 C20B C 0.1229(19) 0.897(3) 0.1315(19) 0.191(9) Uiso 0.43 1 d P A 2 C21B C 0.1810(19) 0.772(3) 0.1524(16) 0.182(8) Uiso 0.42 1 d P A 2 N1B N 0.0638(6) 0.8436(8) 0.2501(5) 0.066(2) Uiso 0.40 1 d P A 2 O1 O 0.4105(2) -0.0365(4) 0.1440(2) 0.1006(12) Uani 1 1 d . . . H1 H 0.3658 -0.0497 0.0977 0.151 Uiso 1 1 calc R . . O2 O 0.3056(3) 0.1137(4) 0.1515(2) 0.1084(13) Uani 1 1 d . . . O3 O 0.14439(18) 0.4150(2) 0.4113(2) 0.0748(9) Uani 1 1 d . . . H3 H 0.1914 0.4637 0.4381 0.112 Uiso 1 1 calc R . . O4 O 0.11851(19) 0.2077(3) 0.3674(2) 0.0800(10) Uani 1 1 d . . . O5 O 0.2177(2) -0.2860(3) 0.3781(2) 0.1017(12) Uani 1 1 d . . . O6 O 0.2854(2) -0.4210(2) 0.48676(18) 0.0719(8) Uani 1 1 d . . . C1 C 0.3819(3) 0.0510(5) 0.1852(3) 0.0659(11) Uani 1 1 d . . . C2 C 0.4541(3) 0.0694(5) 0.2765(3) 0.0710(12) Uani 1 1 d . . . H2A H 0.4828 0.1583 0.2829 0.085 Uiso 1 1 calc R . . H2B H 0.5079 0.0053 0.2888 0.085 Uiso 1 1 calc R . . C3 C 0.4063(2) 0.0517(4) 0.3414(2) 0.0501(9) Uani 1 1 d . . . C4 C 0.3647(2) 0.1613(3) 0.3663(2) 0.0519(9) Uani 1 1 d . . . C5 C 0.3581(4) 0.2976(4) 0.3229(3) 0.0824(14) Uani 1 1 d . . . H5A H 0.3008 0.3453 0.3227 0.124 Uiso 1 1 calc R . . H5B H 0.3523 0.2840 0.2657 0.124 Uiso 1 1 calc R . . H5C H 0.4171 0.3486 0.3531 0.124 Uiso 1 1 calc R . . C6 C 0.3275(2) 0.1461(3) 0.4296(2) 0.0483(9) Uani 1 1 d . . . C7 C 0.2869(3) 0.2685(4) 0.4590(3) 0.0651(11) Uani 1 1 d . . . H7A H 0.2976 0.2570 0.5181 0.078 Uiso 1 1 calc R . . H7B H 0.3242 0.3467 0.4549 0.078 Uiso 1 1 calc R . . C8 C 0.1770(3) 0.2938(4) 0.4086(2) 0.0572(10) Uani 1 1 d . . . C9 C 0.3291(2) 0.0207(4) 0.4674(2) 0.0483(9) Uani 1 1 d . . . C10 C 0.2845(3) 0.0053(5) 0.5337(3) 0.0810(14) Uani 1 1 d . . . H10A H 0.2680 -0.0870 0.5371 0.121 Uiso 1 1 calc R . . H10B H 0.2254 0.0589 0.5181 0.121 Uiso 1 1 calc R . . H10C H 0.3319 0.0342 0.5876 0.121 Uiso 1 1 calc R . . C11 C 0.3708(2) -0.0897(3) 0.4422(2) 0.0482(9) Uani 1 1 d . . . C12 C 0.3765(3) -0.2243(4) 0.4854(3) 0.0625(11) Uani 1 1 d . . . H12A H 0.3866 -0.2084 0.5440 0.075 Uiso 1 1 calc R . . H12B H 0.4343 -0.2721 0.4852 0.075 Uiso 1 1 calc R . . C13 C 0.2846(3) -0.3141(4) 0.4452(3) 0.0586(10) Uani 1 1 d . . . C14 C 0.4082(2) -0.0757(4) 0.3785(2) 0.0508(9) Uani 1 1 d . . . C15 C 0.4475(3) -0.1961(4) 0.3476(3) 0.0824(14) Uani 1 1 d . . . H15A H 0.4524 -0.1750 0.2946 0.124 Uiso 1 1 calc R . . H15B H 0.4029 -0.2702 0.3399 0.124 Uiso 1 1 calc R . . H15C H 0.5121 -0.2194 0.3885 0.124 Uiso 1 1 calc R . . C16 C 0.0160(3) 0.9148(5) 0.2996(3) 0.0867(14) Uani 1 1 d . . . C19 C 0.1159(4) 0.9559(5) 0.2128(4) 0.0959(16) Uani 1 1 d . . . C18 C -0.0883(6) 0.8680(10) 0.3872(6) 0.180(4) 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 0.087(2) 0.120(3) 0.077(2) -0.030(2) 0.0114(18) 0.029(2) O2 0.095(2) 0.159(4) 0.065(2) -0.001(2) 0.0235(19) 0.047(2) O3 0.0550(15) 0.0456(16) 0.105(2) -0.0079(15) 0.0105(16) 0.0018(12) O4 0.0623(17) 0.0512(17) 0.100(2) -0.0150(15) 0.0018(15) -0.0042(13) O5 0.0709(19) 0.079(2) 0.108(3) 0.0425(18) -0.0170(18) -0.0168(15) O6 0.0852(19) 0.0431(16) 0.0739(19) 0.0119(13) 0.0161(15) -0.0106(13) C1 0.058(2) 0.093(3) 0.054(2) 0.003(2) 0.029(2) 0.003(2) C2 0.057(2) 0.100(3) 0.061(3) 0.001(2) 0.028(2) -0.008(2) C3 0.0442(18) 0.059(2) 0.046(2) -0.0016(17) 0.0167(16) -0.0083(15) C4 0.0481(19) 0.044(2) 0.057(2) 0.0005(17) 0.0130(17) -0.0069(15) C5 0.096(3) 0.058(3) 0.088(3) 0.018(2) 0.029(3) -0.010(2) C6 0.0441(18) 0.048(2) 0.047(2) -0.0026(16) 0.0111(16) 0.0002(14) C7 0.059(2) 0.054(2) 0.067(3) -0.0133(19) 0.0079(19) 0.0094(17) C8 0.056(2) 0.043(2) 0.065(2) -0.0066(18) 0.0148(19) -0.0019(17) C9 0.0484(19) 0.055(2) 0.044(2) 0.0037(17) 0.0204(16) 0.0012(15) C10 0.083(3) 0.105(4) 0.065(3) 0.016(2) 0.040(3) 0.010(3) C11 0.0452(18) 0.043(2) 0.052(2) 0.0036(16) 0.0137(16) -0.0016(14) C12 0.059(2) 0.047(2) 0.074(3) 0.0111(19) 0.017(2) -0.0006(16) C13 0.056(2) 0.045(2) 0.071(3) 0.0077(19) 0.021(2) 0.0070(16) C14 0.0404(17) 0.052(2) 0.058(2) -0.0121(17) 0.0165(16) 0.0006(14) C15 0.072(3) 0.076(3) 0.096(4) -0.015(3) 0.030(3) 0.015(2) C16 0.072(3) 0.092(4) 0.088(3) -0.017(3) 0.022(3) -0.015(2) C19 0.096(4) 0.094(4) 0.098(4) 0.005(3) 0.037(3) -0.012(3) C18 0.135(6) 0.230(10) 0.219(9) -0.053(7) 0.119(6) -0.022(6) 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 C18 C17A C16 112.4(11) C19 C20A C21A 117.2(12) C16 N1A C19 110.7(4) C16 C17B C18 115.2(8) C21B C20B C19 109(2) C16 N1B C19 107.0(6) O2 C1 O1 121.5(4) O2 C1 C2 124.7(4) O1 C1 C2 113.7(4) C1 C2 C3 113.8(3) C4 C3 C14 120.1(3) C4 C3 C2 120.3(3) C14 C3 C2 119.6(3) C3 C4 C6 119.8(3) C3 C4 C5 120.0(4) C6 C4 C5 120.1(4) C4 C6 C9 120.8(3) C4 C6 C7 119.0(3) C9 C6 C7 120.2(3) C8 C7 C6 113.8(3) O4 C8 O3 119.4(3) O4 C8 C7 123.8(3) O3 C8 C7 116.8(3) C11 C9 C6 119.4(3) C11 C9 C10 120.7(3) C6 C9 C10 119.9(3) C14 C11 C9 120.3(3) C14 C11 C12 120.2(3) C9 C11 C12 119.5(3) C11 C12 C13 115.1(3) O5 C13 O6 123.3(4) O5 C13 C12 122.0(4) O6 C13 C12 114.8(3) C11 C14 C3 119.5(3) C11 C14 C15 120.4(4) C3 C14 C15 120.0(4) N1B C16 C17B 135.3(6) N1B C16 N1A 55.4(4) C17B C16 N1A 112.4(5) N1B C16 C17A 108.6(7) N1A C16 C17A 130.3(7) C20A C19 N1A 113.7(7) N1A C19 C20B 153.4(12) C20A C19 N1B 72.9(7) N1A C19 N1B 51.8(4) C20B C19 N1B 107.2(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C17A C18 1.506(16) C17A C16 1.571(16) C20A C19 1.488(14) C20A C21A 1.492(19) N1A C16 1.489(7) N1A C19 1.530(8) C17B C16 1.482(11) C17B C18 1.546(12) C20B C21B 1.47(3) C20B C19 1.55(3) N1B C16 1.472(9) N1B C19 1.617(9) O1 C1 1.289(5) O2 C1 1.209(5) O3 C8 1.308(4) O4 C8 1.223(4) O5 C13 1.218(4) O6 C13 1.281(4) C1 C2 1.522(6) C2 C3 1.532(5) C3 C4 1.395(5) C3 C14 1.418(5) C4 C6 1.396(5) C4 C5 1.537(5) C6 C9 1.405(5) C6 C7 1.526(5) C7 C8 1.518(5) C9 C11 1.405(5) C9 C10 1.518(5) C11 C14 1.401(5) C11 C12 1.522(5) C12 C13 1.536(5) C14 C15 1.513(5) 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 O1 H1 O6 0.82 1.83 2.639(5) 168.8 4 O3 H3 O6 0.82 1.74 2.553(4) 174.2 1_565