#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2206265.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_2206265 loop_ _publ_author_name 'Lewis, Thomas C.' 'Tocher, Derek A.' _publ_section_title ; A low-temperature determination of butyramide ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1985 _journal_page_last o1986 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C4 H9 N O' _chemical_formula_moiety 'C4 H9 N O' _chemical_formula_sum 'C4 H9 N O' _chemical_formula_weight 87.12 _chemical_name_common Butyramide _chemical_name_systematic ; Butyramide ; _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 112.070(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.814(3) _cell_length_b 5.9232(17) _cell_length_c 9.701(3) _cell_measurement_reflns_used 1237 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 25.44 _cell_measurement_theta_min 2.24 _cell_volume 522.6(3) _computing_cell_refinement SAINT _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000) and MERCURY (Bruno et al., 2002)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.953 _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method '\w rotation with narrow frames' _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 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4321 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 28.33 _diffrn_reflns_theta_min 2.24 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_correction_T_min 0.9705 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.107 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Plate _exptl_crystal_F_000 192 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.185 _refine_diff_density_min -0.115 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 91 _refine_ls_number_reflns 1244 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0410 _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^)+(0.064P)^2^+0.0651P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1044 _refine_ls_wR_factor_ref 0.1112 _reflns_number_gt 993 _reflns_number_total 1244 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file rn6052.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2206265 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_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_occupancy _atom_site_type_symbol O2 0.62317(10) 0.21606(15) 0.61392(8) 0.0388(3) Uani d 1 O N1 0.58606(12) 0.13501(19) 0.37696(10) 0.0327(3) Uani d 1 N C1 0.65020(13) 0.25241(19) 0.50094(11) 0.0300(3) Uani d 1 C C2 0.76164(15) 0.4276(2) 0.50031(14) 0.0370(3) Uani d 1 C C3 0.77563(15) 0.6237(2) 0.60348(16) 0.0387(3) Uani d 1 C C4 0.89354(17) 0.7892(3) 0.60401(19) 0.0457(4) Uani d 1 C H1 0.5216(15) 0.022(3) 0.3760(14) 0.042(4) Uiso d 1 H H2 0.6058(15) 0.164(2) 0.2966(16) 0.037(3) Uiso d 1 H H3 0.7428(17) 0.475(3) 0.4012(17) 0.055(4) Uiso d 1 H H4 0.860(2) 0.344(3) 0.5341(19) 0.061(5) Uiso d 1 H H5 0.680(2) 0.701(3) 0.5663(18) 0.054(4) Uiso d 1 H H6 0.7966(16) 0.564(2) 0.7050(18) 0.050(4) Uiso d 1 H H7 0.8744(19) 0.845(3) 0.506(2) 0.063(5) Uiso d 1 H H8 0.898(2) 0.914(3) 0.664(2) 0.070(5) Uiso d 1 H H9 0.9914(18) 0.716(3) 0.6376(16) 0.049(4) Uiso 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 O2 0.0579(6) 0.0422(5) 0.0254(4) -0.0114(4) 0.0263(4) -0.0053(3) N1 0.0456(6) 0.0368(6) 0.0222(5) -0.0047(5) 0.0202(4) -0.0012(4) C1 0.0398(6) 0.0317(6) 0.0240(5) 0.0024(5) 0.0183(5) 0.0006(4) C2 0.0475(7) 0.0403(7) 0.0297(6) -0.0074(6) 0.0218(5) -0.0019(5) C3 0.0383(7) 0.0353(7) 0.0453(8) 0.0003(5) 0.0190(6) -0.0028(5) C4 0.0435(8) 0.0382(8) 0.0549(9) -0.0031(6) 0.0179(7) -0.0013(7) 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 C1 N1 H1 118.8(8) C1 N1 H2 120.7(9) H1 N1 H2 120.5(13) O2 C1 N1 121.64(11) O2 C1 C2 121.28(10) N1 C1 C2 117.05(10) C3 C2 C1 114.40(10) C3 C2 H3 112.4(10) C1 C2 H3 109.9(10) C3 C2 H4 108.6(10) C1 C2 H4 105.5(10) H3 C2 H4 105.5(13) C2 C3 C4 112.36(11) C2 C3 H5 106.1(9) C4 C3 H5 109.0(9) C2 C3 H6 108.5(9) C4 C3 H6 110.7(9) H5 C3 H6 110.0(13) C3 C4 H7 110.9(11) C3 C4 H8 111.5(11) H7 C4 H8 107.2(16) C3 C4 H9 111.3(9) H7 C4 H9 106.4(14) H8 C4 H9 109.4(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O2 C1 1.2395(13) N1 C1 1.3257(15) N1 H1 0.919(16) N1 H2 0.887(15) C1 C2 1.5091(17) C2 C3 1.5057(18) C2 H3 0.950(16) C2 H4 1.022(18) C3 C4 1.515(2) C3 H5 0.985(18) C3 H6 0.993(16) C4 H7 0.954(18) C4 H8 0.93(2) C4 H9 0.990(16) 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 O2 3_656 0.919(16) 2.030(16) 2.9470(15) 175.9(13) N1 H2 O2 4_565 0.887(15) 1.976(15) 2.8496(14) 167.9(13) 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 O2 C1 C2 C3 -30.35(18) N1 C1 C2 C3 151.62(12) C1 C2 C3 C4 177.41(12)