#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/16/2101650.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_2101650 loop_ _publ_author_name 'M\"uller, G.' 'Lutz, M.' 'Harder, S.' _publ_section_title ; Methyl group conformation-determining intermolecular C--H···O hydrogen bonds: structure of N-methyl-2-pyrrolidone ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 1014 _journal_page_last 1022 _journal_paper_doi 10.1107/S0108768196008300 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C5 H9 N O' _chemical_formula_weight 99.134 _chemical_melting_point 'see text' _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 111.03(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.221(3) _cell_length_b 12.076(2) _cell_length_c 7.529(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 168(2) _cell_measurement_theta_max 21.4 _cell_measurement_theta_min 14.0 _cell_volume 527.9(4) _computing_cell_refinement 'CAD4 (Enraf-Nonius, 1989)' _computing_data_collection 'CAD4 (Enraf-Nonius, 1989)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics ; ORTEPII (Johnson, 1976) SCHAKAL92 (Keller, 1992) ; _computing_publication_material ; SHELXL-93 (Sheldrick, 1993) PLATON (Spek, 1990) ; _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1985)' _diffrn_ambient_temperature 168(2) _diffrn_measurement_device 'Enraf-Nonius CAD4 4-circle' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.07 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number '3721, of which 107 were rejected' _diffrn_reflns_theta_max 27.32 _diffrn_reflns_theta_min 3.35 _diffrn_standards_decay_% 1.8 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_type 'Empirical, nine \y scans' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_meas ? _exptl_crystal_description 'see text' _exptl_crystal_F_000 216 _exptl_crystal_size_max 'see text' _exptl_crystal_size_mid 'see text' _exptl_crystal_size_min 'see text' _refine_diff_density_max 0.197 _refine_diff_density_min -0.328 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.055 _refine_ls_goodness_of_fit_obs 1.087 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1190 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_restrained_S_obs 1.087 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_obs 0.0466 _refine_ls_shift/esd_max 0.008 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0681P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1236 _refine_ls_wR_factor_obs 0.1146 _reflns_number_observed 980 _reflns_number_total 1190 _reflns_observed_criterion F^2^>2sigma(F^2^) _[local]_cod_data_source_file se0197.cif _[local]_cod_data_source_block k130 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0681P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.0681P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2101650 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_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 N 0.0259(5) 0.0179(5) 0.0358(5) 0.0011(4) 0.0102(4) 0.0011(4) O 0.0321(5) 0.0270(5) 0.0535(6) 0.0087(4) 0.0138(4) -0.0029(4) C1 0.0264(6) 0.0217(5) 0.0270(5) 0.0025(4) 0.0082(4) -0.0018(4) C2 0.0309(6) 0.0215(6) 0.0381(6) -0.0024(5) 0.0121(5) -0.0031(5) C3 0.0384(7) 0.0192(5) 0.0414(7) 0.0039(5) 0.0150(5) 0.0017(5) C4 0.0287(6) 0.0246(6) 0.0398(7) 0.0057(5) 0.0111(5) 0.0041(5) C5 0.0379(7) 0.0218(6) 0.0432(7) -0.0054(6) 0.0144(6) -0.0007(5) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_occupancy _atom_site_type_symbol N 0.2255(2) 0.30250(10) 0.16720(10) 0.0270(10) Uani d 1 N O -0.1406(2) 0.36290(10) 0.11310(10) 0.0380(10) Uani d 1 O C1 0.0006(2) 0.28830(10) 0.1369(2) 0.0250(10) Uani d 1 C C2 -0.0453(2) 0.16530(10) 0.1385(2) 0.0300(10) Uani d 1 C C3 0.1750(2) 0.10970(10) 0.1424(2) 0.0330(10) Uani d 1 C C4 0.3575(2) 0.20020(10) 0.2062(2) 0.0310(10) Uani d 1 C C5 0.3343(2) 0.41010(10) 0.1872(2) 0.0340(10) Uani d 1 C H21 -0.180(3) 0.1468(14) 0.030(3) 0.050(5) Uiso d 1 H H22 -0.082(3) 0.1477(15) 0.252(3) 0.056(5) Uiso d 1 H H31 0.158(3) 0.0873(16) 0.012(2) 0.048(4) Uiso d 1 H H32 0.222(3) 0.0456(16) 0.226(2) 0.052(5) Uiso d 1 H H41 0.456(3) 0.1953(14) 0.341(2) 0.041(4) Uiso d 1 H H42 0.469(3) 0.2004(16) 0.136(2) 0.052(5) Uiso d 1 H H51 0.469(3) 0.4113(18) 0.139(2) 0.059(5) Uiso d 1 H H52 0.407(3) 0.4347(16) 0.324(2) 0.051(4) Uiso d 1 H H53 0.226(3) 0.4619(18) 0.114(3) 0.060(5) Uiso d 1 H 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 N C5 . 123.40(10) yes C1 N C4 . 113.80(10) yes C5 N C4 . 122.20(10) yes O C1 N . 125.30(10) yes O C1 C2 . 126.50(10) yes N C1 C2 . 108.20(10) yes C1 C2 C3 . 105.20(10) yes C1 C2 H21 . 109.3(10) ? C3 C2 H21 . 114.6(10) ? C1 C2 H22 . 108.8(11) ? C3 C2 H22 . 112.2(11) ? H21 C2 H22 . 106.6(14) ? C2 C3 C4 . 104.70(10) yes C2 C3 H31 . 109.2(10) ? C4 C3 H31 . 108.1(10) ? C2 C3 H32 . 115.1(10) ? C4 C3 H32 . 110.4(11) ? H31 C3 H32 . 109.0(15) ? N C4 C3 . 104.00(10) yes N C4 H41 . 110.9(10) ? C3 C4 H41 . 113.5(10) ? N C4 H42 . 109.7(11) ? C3 C4 H42 . 114.2(11) ? H41 C4 H42 . 104.7(14) ? N C5 H51 . 113.0(10) yes N C5 H52 . 113.0(10) yes H51 C5 H52 . 103.0(10) yes N C5 H53 . 109.0(10) yes H51 C5 H53 . 107(2) yes H52 C5 H53 . 112(2) yes C5 H53 O 3_565 148(2) no C5 H51 O 1_655 160.0(10) no 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 N C1 . 1.345(2) yes N C5 . 1.4470(10) yes N C4 . 1.4540(10) yes O C1 . 1.2250(10) yes O C5 3_565 3.482(2) no O C5 1_455 3.552(2) no C1 C2 . 1.514(2) yes C2 C3 . 1.517(2) yes C2 H21 . 0.96(2) ? C2 H22 . 0.98(2) ? C3 C4 . 1.524(2) yes C3 H31 . 0.99(2) ? C3 H32 . 0.98(2) ? C4 H41 . 0.98(2) ? C4 H42 . 1.01(2) ? C5 O 1_655 3.552(2) yes C5 O 3_565 3.482(2) yes C5 H51 . 1.03(2) yes C5 H52 . 1.01(2) yes C5 H53 . 0.94(2) yes 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 C5 N C1 O 3.9(2) yes C4 N C1 O 175.30(10) yes C5 N C1 C2 -175.80(10) yes C4 N C1 C2 -4.50(10) yes O C1 C2 C3 171.50(10) yes N C1 C2 C3 -8.80(10) yes C1 C2 C3 C4 17.60(10) yes C1 N C4 C3 15.70(10) yes C5 N C4 C3 -172.80(10) yes C2 C3 C4 N -19.80(10) yes