#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2016797.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_2016797 loop_ _publ_author_name 'Bond, Andrew D.' 'Davies, John E.' 'Parsons, Simon' _publ_section_title ; Azetidine, pyrrolidine and hexamethyleneimine at 170K ; _journal_coeditor_code FA3160 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o543 _journal_page_last o546 _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C4 H9 N' _chemical_formula_moiety 'C4 H9 N' _chemical_formula_sum 'C4 H9 N' _chemical_formula_weight 71.12 _chemical_melting_point 210 _chemical_name_common pyrrolidine _chemical_name_systematic ; pyrrolidine ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 110.451(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.6753(8) _cell_length_b 5.2078(5) _cell_length_c 10.7108(10) _cell_measurement_reflns_used 2626 _cell_measurement_temperature 170(2) _cell_measurement_theta_max 26.06 _cell_measurement_theta_min 2.51 _cell_volume 453.41(7) _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 170(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker Nonius X8 APEXII CCD area-detector' _diffrn_measurement_method 'thin-slice \w and \f scans' _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 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5429 _diffrn_reflns_theta_full 26.06 _diffrn_reflns_theta_max 26.06 _diffrn_reflns_theta_min 3.96 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_correction_T_min 0.853 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.042 _exptl_crystal_density_method 'not measured' _exptl_crystal_description cylinder _exptl_crystal_F_000 160 _exptl_crystal_size_max 0.35 _exptl_crystal_size_rad 0.15 _refine_diff_density_max 0.156 _refine_diff_density_min -0.131 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 50 _refine_ls_number_reflns 900 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0416 _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^)+(0.0456P)^2^+0.1266P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1051 _refine_ls_wR_factor_ref 0.1100 _reflns_number_gt 760 _reflns_number_total 900 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fa3160.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2016797 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_type_symbol _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 N N1 0.10684(13) 0.5232(2) 0.30411(12) 0.0402(3) Uani d . 1 H H1 0.038(2) 0.411(3) 0.2626(17) 0.054(5) Uiso d . 1 C C2 0.18779(17) 0.4308(3) 0.43977(13) 0.0422(4) Uani d . 1 H H2A 0.1061 0.3551 0.4745 0.051 Uiso calc R 1 H H2B 0.2441 0.5741 0.4989 0.051 Uiso calc R 1 C C3 0.31260(16) 0.2278(3) 0.43463(13) 0.0423(4) Uani d . 1 H H3A 0.4145 0.2400 0.5138 0.051 Uiso calc R 1 H H3B 0.2663 0.0529 0.4305 0.051 Uiso calc R 1 C C4 0.34677(18) 0.2893(3) 0.30783(15) 0.0463(4) Uani d . 1 H H4A 0.3177 0.1419 0.2455 0.056 Uiso calc R 1 H H4B 0.4643 0.3318 0.3284 0.056 Uiso calc R 1 C C5 0.23822(19) 0.5199(3) 0.24830(14) 0.0465(4) Uani d . 1 H H5A 0.3032 0.6804 0.2713 0.056 Uiso calc R 1 H H5B 0.1914 0.5048 0.1500 0.056 Uiso calc R 1 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 0.0346(6) 0.0328(6) 0.0469(7) 0.0027(5) 0.0062(5) 0.0002(5) C2 0.0442(8) 0.0433(8) 0.0425(8) 0.0096(6) 0.0192(6) 0.0010(6) C3 0.0429(7) 0.0417(8) 0.0406(7) 0.0109(6) 0.0124(6) 0.0015(6) C4 0.0483(8) 0.0421(8) 0.0554(9) 0.0047(6) 0.0269(7) -0.0024(6) C5 0.0644(9) 0.0331(7) 0.0477(8) -0.0005(6) 0.0270(7) 0.0012(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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C5 103.38(10) C2 N1 H1 107.6(12) C5 N1 H1 106.5(11) N1 C2 C3 107.05(10) N1 C2 H2A 110.3 C3 C2 H2A 110.3 N1 C2 H2B 110.3 C3 C2 H2B 110.3 H2A C2 H2B 108.6 C4 C3 C2 104.36(11) C4 C3 H3A 110.9 C2 C3 H3A 110.9 C4 C3 H3B 110.9 C2 C3 H3B 110.9 H3A C3 H3B 108.9 C3 C4 C5 104.77(11) C3 C4 H4A 110.8 C5 C4 H4A 110.8 C3 C4 H4B 110.8 C5 C4 H4B 110.8 H4A C4 H4B 108.9 N1 C5 C4 107.14(11) N1 C5 H5A 110.3 C4 C5 H5A 110.3 N1 C5 H5B 110.3 C4 C5 H5B 110.3 H5A C5 H5B 108.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.4570(17) N1 C5 1.4604(18) N1 H1 0.84(2) C2 C3 1.5281(17) C2 H2A 0.99 C2 H2B 0.99 C3 C4 1.5220(19) C3 H3A 0.99 C3 H3B 0.99 C4 C5 1.522(2) C4 H4A 0.99 C4 H4B 0.99 C5 H5A 0.99 C5 H5B 0.99 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 N1 2_545 0.84(2) 2.35(2) 3.1716(13) 163.7(15) 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 C5 N1 C2 C3 -35.77(14) N1 C2 C3 C4 22.47(15) C2 C3 C4 C5 -0.69(15) C2 N1 C5 C4 35.32(14) C3 C4 C5 N1 -21.25(15)