#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/45/2204571.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_2204571 loop_ _publ_author_name 'Wei Xu' 'Yin-Xiang Lu' 'Zhen-Guang Zou' 'Chun-Ming Liu' 'Bi-Jian Lan' 'Hui Zhou' _publ_section_title ; 1,1,1-Tris[(pyrrol-1-yl)methyl]ethane: herring-bone packing of supramolecular assemblies in a homochiral crystal from chemically symmetric molecules ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2171 _journal_page_last o2173 _journal_paper_doi 10.1107/S1600536804027011 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C17 H21 N3' _chemical_formula_moiety 'C17 H21 N3' _chemical_formula_sum 'C17 H21 N3' _chemical_formula_weight 267.37 _chemical_name_systematic ; 1,1,1-Tris[(pyrrol-1-yl)methyl]ethane ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.7625(14) _cell_length_b 11.2496(19) _cell_length_c 17.542(3) _cell_measurement_reflns_used 2807 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 22.360 _cell_measurement_theta_min 2.248 _cell_volume 1531.9(5) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7054 _diffrn_reflns_theta_full 26.01 _diffrn_reflns_theta_max 26.01 _diffrn_reflns_theta_min 2.15 _diffrn_standards_decay_% 3.92 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_T_max 0.9726 _exptl_absorpt_correction_T_min 0.9527 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.228 _refine_diff_density_min -0.178 _refine_ls_abs_structure_details 'none, Friedel pairs merged' _refine_ls_extinction_coef 0.033(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 1746 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.172 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0570 _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^)+(0.0751P)^2^+0.0401P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1346 _refine_ls_wR_factor_ref 0.1379 _reflns_number_gt 1594 _reflns_number_total 1746 _reflns_threshold_expression I>2\s(I) _cod_data_source_file su6135.cif _cod_data_source_block I _cod_original_cell_volume 1531.8(5) _cod_database_code 2204571 _cod_database_fobs_code 2204571 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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_type_symbol N1 0.4762(3) 0.22057(18) 0.08017(12) 0.0493(6) Uani d . 1 N N3 0.0066(3) 0.36777(19) 0.18019(12) 0.0519(6) Uani d . 1 N N2 0.4206(3) 0.59859(19) 0.08031(13) 0.0516(6) Uani d . 1 N C1 0.2975(3) 0.3989(2) 0.11865(13) 0.0425(6) Uani d . 1 C C2 0.4154(4) 0.3384(2) 0.05996(15) 0.0503(7) Uani d . 1 C H2A 0.3536 0.3329 0.0120 0.060 Uiso calc R 1 H H2B 0.5147 0.3890 0.0516 0.060 Uiso calc R 1 H C3 0.3995(5) 0.1152(2) 0.06415(19) 0.0674(9) Uani d . 1 C H3 0.2953 0.1049 0.0388 0.081 Uiso calc R 1 H C4 0.5031(6) 0.0268(3) 0.0920(2) 0.0927(14) Uani d . 1 C H4 0.4814 -0.0544 0.0893 0.111 Uiso calc R 1 H C5 0.6459(6) 0.0798(3) 0.1251(2) 0.0863(12) Uani d . 1 C H5 0.7378 0.0408 0.1481 0.104 Uiso calc R 1 H C6 0.6269(4) 0.1989(3) 0.11764(18) 0.0653(8) Uani d . 1 C H6 0.7037 0.2562 0.1351 0.078 Uiso calc R 1 H C7 0.2652(3) 0.5279(2) 0.09090(18) 0.0532(7) Uani d . 1 C H7A 0.2032 0.5248 0.0429 0.064 Uiso calc R 1 H H7B 0.1917 0.5678 0.1276 0.064 Uiso calc R 1 H C8 0.5097(5) 0.6093(2) 0.01356(17) 0.0640(7) Uani d . 1 C H8 0.4809 0.5736 -0.0325 0.077 Uiso calc R 1 H C9 0.6474(5) 0.6808(2) 0.0259(2) 0.0715(9) Uani d . 1 C H9 0.7302 0.7026 -0.0098 0.086 Uiso calc R 1 H C10 0.6416(4) 0.7159(2) 0.1029(2) 0.0701(9) Uani d . 1 C H10 0.7199 0.7652 0.1276 0.084 Uiso calc R 1 H C11 0.5016(4) 0.6647(2) 0.13430(18) 0.0632(8) Uani d . 1 C H11 0.4663 0.6733 0.1847 0.076 Uiso calc R 1 H C12 0.1220(3) 0.3341(2) 0.11952(16) 0.0507(6) Uani d . 1 C H12A 0.0648 0.3486 0.0713 0.061 Uiso calc R 1 H H12B 0.1431 0.2493 0.1231 0.061 Uiso calc R 1 H C13 -0.0089(5) 0.3112(3) 0.2481(2) 0.0726(9) Uani d . 1 C H13 0.0474 0.2414 0.2617 0.087 Uiso calc R 1 H C14 -0.1189(5) 0.3724(4) 0.2927(2) 0.0877(12) Uani d . 1 C H14 -0.1518 0.3527 0.3421 0.105 Uiso calc R 1 H C15 -0.1748(4) 0.4716(4) 0.2506(2) 0.0833(11) Uani d . 1 C H15 -0.2512 0.5299 0.2670 0.100 Uiso calc R 1 H C16 -0.0972(4) 0.4662(3) 0.1824(2) 0.0636(8) Uani d . 1 C H16 -0.1115 0.5206 0.1430 0.076 Uiso calc R 1 H C17 0.3779(3) 0.3972(3) 0.19737(15) 0.0530(7) Uani d . 1 C H17A 0.3075 0.4423 0.2319 0.079 Uiso calc R 1 H H17B 0.4909 0.4317 0.1951 0.079 Uiso calc R 1 H H17C 0.3862 0.3167 0.2150 0.079 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 N1 0.0539(14) 0.0460(10) 0.0479(12) 0.0043(10) 0.0108(11) 0.0007(9) N3 0.0374(11) 0.0616(12) 0.0567(12) -0.0002(10) -0.0016(11) 0.0007(10) N2 0.0491(12) 0.0446(11) 0.0611(14) -0.0001(10) -0.0031(11) 0.0006(11) C1 0.0364(13) 0.0479(13) 0.0432(12) 0.0012(11) -0.0025(11) -0.0019(12) C2 0.0542(16) 0.0507(13) 0.0459(13) 0.0032(12) 0.0064(12) 0.0057(11) C3 0.0707(19) 0.0556(17) 0.076(2) -0.0061(16) 0.0282(17) -0.0085(15) C4 0.116(3) 0.0490(16) 0.113(3) 0.010(2) 0.065(3) 0.0133(17) C5 0.095(3) 0.082(2) 0.081(2) 0.037(2) 0.034(2) 0.032(2) C6 0.0575(19) 0.079(2) 0.0597(17) 0.0173(16) 0.0087(15) 0.0076(16) C7 0.0444(15) 0.0522(15) 0.0630(16) 0.0041(12) -0.0041(14) -0.0016(13) C8 0.077(2) 0.0559(14) 0.0587(16) -0.0050(17) 0.0019(17) 0.0038(13) C9 0.069(2) 0.0516(15) 0.094(2) -0.0074(15) 0.013(2) 0.0174(16) C10 0.068(2) 0.0489(15) 0.093(2) -0.0138(15) -0.0143(19) 0.0026(16) C11 0.0703(19) 0.0488(14) 0.0704(18) -0.0005(16) -0.0040(18) -0.0105(13) C12 0.0419(14) 0.0569(14) 0.0533(14) 0.0000(12) -0.0036(12) -0.0056(13) C13 0.0522(17) 0.100(2) 0.0652(18) -0.006(2) 0.0006(17) 0.0194(17) C14 0.059(2) 0.142(4) 0.0611(19) -0.016(2) 0.0111(17) -0.005(2) C15 0.0469(17) 0.100(3) 0.103(3) -0.0091(19) 0.017(2) -0.034(2) C16 0.0402(15) 0.0649(17) 0.086(2) -0.0006(14) -0.0018(16) -0.0071(16) C17 0.0446(15) 0.0672(16) 0.0472(13) -0.0009(14) -0.0012(12) -0.0057(13) 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 0.0000 '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 0.0000 '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 C3 N1 C6 108.7(3) y C3 N1 C2 127.2(3) ? C6 N1 C2 124.1(2) ? C11 N2 C8 108.3(2) y C11 N2 C7 126.4(2) ? C8 N2 C7 125.3(3) ? C13 N3 C16 107.6(3) y C13 N3 C12 125.5(3) ? C16 N3 C12 126.8(3) ? C17 C1 C2 111.1(2) ? C17 C1 C12 110.4(2) ? C2 C1 C12 108.8(2) ? C17 C1 C7 111.3(2) ? C2 C1 C7 107.5(2) ? C12 C1 C7 107.6(2) ? N1 C2 C1 115.8(2) y N1 C2 H2A 108.3 ? C1 C2 H2A 108.3 ? N1 C2 H2B 108.3 ? C1 C2 H2B 108.3 ? H2A C2 H2B 107.4 ? N1 C3 C4 107.6(3) ? N1 C3 H3 126.2 ? C4 C3 H3 126.2 ? C3 C4 C5 107.8(3) ? C3 C4 H4 126.1 ? C5 C4 H4 126.1 ? C6 C5 C4 107.4(4) ? C6 C5 H5 126.3 ? C4 C5 H5 126.3 ? C5 C6 N1 108.5(4) ? C5 C6 H6 125.8 ? N1 C6 H6 125.8 ? N2 C7 C1 114.6(2) y N2 C7 H7A 108.6 ? C1 C7 H7A 108.6 ? N2 C7 H7B 108.6 ? C1 C7 H7B 108.6 ? H7A C7 H7B 107.6 ? C9 C8 N2 108.4(3) ? C9 C8 H8 125.8 ? N2 C8 H8 125.8 ? C8 C9 C10 107.1(3) ? C8 C9 H9 126.5 ? C10 C9 H9 126.5 ? C11 C10 C9 107.4(3) ? C11 C10 H10 126.3 ? C9 C10 H10 126.3 ? C10 C11 N2 108.8(3) ? C10 C11 H11 125.6 ? N2 C11 H11 125.6 ? N3 C12 C1 115.5(2) y N3 C12 H12A 108.4 ? C1 C12 H12A 108.4 ? N3 C12 H12B 108.4 ? C1 C12 H12B 108.4 ? H12A C12 H12B 107.5 ? C14 C13 N3 109.1(3) ? C14 C13 H13 125.5 ? N3 C13 H13 125.5 ? C13 C14 C15 107.2(3) ? C13 C14 H14 126.4 ? C15 C14 H14 126.4 ? C16 C15 C14 107.1(3) ? C16 C15 H15 126.5 ? C14 C15 H15 126.5 ? C15 C16 N3 109.0(3) ? C15 C16 H16 125.5 ? N3 C16 H16 125.5 ? C1 C17 H17A 109.5 ? C1 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? C1 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C3 1.356(4) ? N1 C6 1.364(4) ? N1 C2 1.451(3) y N2 C11 1.359(4) ? N2 C8 1.365(4) ? N2 C7 1.457(3) y N3 C13 1.355(4) ? N3 C16 1.370(4) ? N3 C12 1.442(3) y C1 C17 1.516(3) ? C1 C2 1.536(4) ? C1 C12 1.545(3) ? C1 C7 1.552(4) ? C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 C4 1.370(5) ? C3 H3 0.9300 ? C4 C5 1.386(6) y C4 H4 0.9300 ? C5 C6 1.353(5) ? C5 H5 0.9300 ? C6 H6 0.9300 ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 C9 1.355(4) ? C8 H8 0.9300 ? C9 C10 1.409(5) y C9 H9 0.9300 ? C10 C11 1.347(4) ? C10 H10 0.9300 ? C11 H11 0.9300 ? C12 H12A 0.9700 ? C12 H12B 0.9700 ? C13 C14 1.348(5) ? C13 H13 0.9300 ? C14 C15 1.406(5) y C14 H14 0.9300 ? C15 C16 1.341(5) ? C15 H15 0.9300 ? C16 H16 0.9300 ? C17 H17A 0.9600 ? C17 H17B 0.9600 ? C17 H17C 0.9600 ? 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 C3 N1 C2 C1 90.1(3) yes C6 N1 C2 C1 -91.8(3) yes C8 N2 C7 C1 92.3(3) yes C11 N2 C7 C1 -87.8(3) yes C13 N3 C12 C1 -94.5(3) yes C16 N3 C12 C1 80.4(3) yes C17 C1 C2 N1 51.4(3) yes C17 C1 C7 N2 64.1(3) yes C17 C1 C12 N3 48.2(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130274 2 PubChem 86033537