#------------------------------------------------------------------------------ #$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $ #$Revision: 326 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206688.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_2206688 loop_ _publ_author_name 'Zheng, Peng-Wu' 'Wang, Wei' 'Duan, Xue-Min' _publ_section_title ; Ethyl N-(2-pyridyl)carbamate ; _journal_coeditor_code FL6182 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o2970 _journal_page_last o2971 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C8 H10 N2 O2' _chemical_formula_moiety 'C8 H10 N2 O2' _chemical_formula_sum 'C8 H10 N2 O2' _chemical_formula_weight 166.18 _chemical_melting_point .363E-305 _chemical_name_systematic ; Ethyl N-(2-pyridyl)carbamate ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.211(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.621(4) _cell_length_b 7.497(3) _cell_length_c 11.839(5) _cell_measurement_reflns_used 1352 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 24.76 _cell_measurement_theta_min 3.22 _cell_volume 852.6(6) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _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 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4629 _diffrn_reflns_theta_full 26.38 _diffrn_reflns_theta_max 26.38 _diffrn_reflns_theta_min 2.12 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.168 _refine_diff_density_min -0.142 _refine_ls_extinction_coef 0.027(4) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 115 _refine_ls_number_reflns 1741 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0370 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.05P)^2^+0.0996P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0907 _refine_ls_wR_factor_ref 0.1092 _reflns_number_gt 1090 _reflns_number_total 1741 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fl6182.cif 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_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_ _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 O1 0.71656(13) 0.1381(2) -0.04711(10) 0.0741(5) Uani d . 1 O O2 0.74023(12) 0.09654(18) 0.14117(9) 0.0620(4) Uani d . 1 O N1 1.05070(15) 0.3374(2) -0.21729(11) 0.0589(4) Uani d . 1 N N2 0.92267(14) 0.1866(2) 0.05422(10) 0.0497(4) Uani d D 1 N C1 1.00699(16) 0.2551(2) -0.02740(12) 0.0439(4) Uani d . 1 C C2 1.13859(18) 0.3137(3) 0.00687(14) 0.0558(5) Uani d . 1 C H2 1.1693 0.3062 0.0826 0.067 Uiso calc R 1 H C3 1.22383(19) 0.3830(3) -0.07099(15) 0.0616(5) Uani d . 1 C H3 1.3126 0.4232 -0.0487 0.074 Uiso calc R 1 H C4 1.17636(19) 0.3922(3) -0.18218(15) 0.0593(5) Uani d . 1 C H4 1.2347 0.4387 -0.2349 0.071 Uiso calc R 1 H C5 0.96760(18) 0.2705(3) -0.14166(13) 0.0538(5) Uani d . 1 C H5 0.8791 0.2323 -0.1665 0.065 Uiso calc R 1 H C6 0.78704(18) 0.1406(2) 0.04020(14) 0.0514(5) Uani d . 1 C C7 0.59715(17) 0.0395(3) 0.14151(15) 0.0634(5) Uani d . 1 C H7A 0.5821 -0.0644 0.0935 0.076 Uiso calc R 1 H H7B 0.5356 0.1340 0.1135 0.076 Uiso calc R 1 H C8 0.5691(2) -0.0048(3) 0.26110(17) 0.0776(6) Uani d . 1 C H8A 0.6304 -0.0987 0.2877 0.116 Uiso calc R 1 H H8B 0.4743 -0.0432 0.2649 0.116 Uiso calc R 1 H H8C 0.5846 0.0989 0.3076 0.116 Uiso calc R 1 H H2A 0.9647(16) 0.176(2) 0.1271(9) 0.061(5) Uiso d D 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 O1 0.0603(8) 0.1115(12) 0.0482(7) -0.0164(7) -0.0159(6) 0.0092(7) O2 0.0511(7) 0.0906(10) 0.0438(7) -0.0099(6) -0.0012(5) 0.0000(6) N1 0.0611(10) 0.0764(12) 0.0389(8) -0.0014(8) -0.0007(7) 0.0024(7) N2 0.0490(8) 0.0667(10) 0.0326(7) -0.0017(7) -0.0052(6) -0.0024(7) C1 0.0480(9) 0.0471(10) 0.0358(8) 0.0043(7) -0.0034(7) -0.0052(7) C2 0.0559(10) 0.0706(12) 0.0397(9) -0.0012(9) -0.0080(8) -0.0020(9) C3 0.0516(10) 0.0758(14) 0.0562(11) -0.0072(9) -0.0059(9) -0.0008(10) C4 0.0564(11) 0.0721(13) 0.0494(10) -0.0003(9) 0.0026(8) 0.0035(9) C5 0.0537(10) 0.0685(13) 0.0382(9) -0.0031(9) -0.0052(7) -0.0035(8) C6 0.0545(10) 0.0579(12) 0.0409(9) -0.0007(8) -0.0043(8) -0.0026(8) C7 0.0461(10) 0.0804(14) 0.0630(12) -0.0019(9) -0.0020(9) -0.0017(10) C8 0.0586(12) 0.1022(18) 0.0728(13) -0.0006(12) 0.0106(10) 0.0112(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C6 1.2042(19) yes O2 C6 1.342(2) yes O2 C7 1.442(2) yes N1 C4 1.322(2) ? N1 C5 1.331(2) ? N2 C6 1.351(2) yes N2 C1 1.394(2) yes N2 H2A 0.936(9) ? C1 C2 1.380(2) ? C1 C5 1.389(2) ? C2 C3 1.370(2) ? C2 H2 0.9300 ? C3 C4 1.371(2) ? C3 H3 0.9300 ? C4 H4 0.9300 ? C5 H5 0.9300 ? C7 C8 1.493(3) ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 H8A 0.9600 ? C8 H8B 0.9600 ? C8 H8C 0.9600 ? 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 C6 O2 C7 116.33(12) ? C4 N1 C5 118.61(14) ? C6 N2 C1 127.19(13) ? C6 N2 H2A 117.2(10) ? C1 N2 H2A 115.5(10) ? C2 C1 C5 117.11(16) ? C2 C1 N2 118.27(13) ? C5 C1 N2 124.61(15) ? C3 C2 C1 119.81(15) ? C3 C2 H2 120.1 ? C1 C2 H2 120.1 ? C2 C3 C4 119.04(17) ? C2 C3 H3 120.5 ? C4 C3 H3 120.5 ? N1 C4 C3 122.41(17) ? N1 C4 H4 118.8 ? C3 C4 H4 118.8 ? N1 C5 C1 123.02(16) ? N1 C5 H5 118.5 ? C1 C5 H5 118.5 ? O1 C6 O2 124.05(16) ? O1 C6 N2 127.08(16) yes O2 C6 N2 108.87(13) yes O2 C7 C8 106.97(14) ? O2 C7 H7A 110.3 ? C8 C7 H7A 110.3 ? O2 C7 H7B 110.3 ? C8 C7 H7B 110.3 ? H7A C7 H7B 108.6 ? C7 C8 H8A 109.5 ? C7 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? C7 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? 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 C6 N2 C1 C2 172.38(17) ? C6 N2 C1 C5 -7.0(3) ? C5 C1 C2 C3 -0.1(3) ? N2 C1 C2 C3 -179.54(17) ? C1 C2 C3 C4 -0.2(3) ? C5 N1 C4 C3 -0.1(3) ? C2 C3 C4 N1 0.3(3) ? C4 N1 C5 C1 -0.2(3) ? C2 C1 C5 N1 0.3(3) ? N2 C1 C5 N1 179.69(16) yes C7 O2 C6 O1 1.5(3) ? C7 O2 C6 N2 -178.59(15) yes C1 N2 C6 O1 5.8(3) ? C1 N2 C6 O2 -174.15(15) yes C6 O2 C7 C8 179.11(17) yes 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 _geom_hbond_publ_flag N2 H2A N1 4_566 0.936(9) 1.979(11) 2.914(4) 178.1(4) yes