#------------------------------------------------------------------------------ #$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $ #$Revision: 176798 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/44/2234430.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_2234430 loop_ _publ_author_name 'Li, Zhi' _publ_section_title ; 3-Oxapentane-1,5-diyl dicarbamate ; _journal_coeditor_code TK5072 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1171 _journal_paper_doi 10.1107/S1600536812011981 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C6 H12 N2 O5' _chemical_formula_moiety 'C6 H12 N2 O5' _chemical_formula_sum 'C6 H12 N2 O5' _chemical_formula_weight 192.18 _chemical_melting_point 428 _chemical_name_systematic ; 3-Oxapentane-1,5-diyl dicarbamate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/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 99.393(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.263(4) _cell_length_b 5.1412(15) _cell_length_c 12.276(4) _cell_measurement_reflns_used 1304 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 26.03 _cell_measurement_theta_min 3.36 _cell_volume 888.1(5) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'SMART (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w 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 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 2358 _diffrn_reflns_theta_full 26.31 _diffrn_reflns_theta_max 26.31 _diffrn_reflns_theta_min 2.90 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.158 _refine_diff_density_min -0.142 _refine_ls_extinction_coef 0.029(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)' _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 69 _refine_ls_number_reflns 904 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0305 _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^)+(0.0407P)^2^+0.3363P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.0835 _reflns_number_gt 748 _reflns_number_total 904 _reflns_threshold_expression I>2\s(I) _cod_data_source_file tk5072.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2234430 _cod_database_fobs_code 2234430 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 _atom_site_symmetry_multiplicity O O1 0.25476(6) 0.5124(2) 0.40946(8) 0.0461(3) Uani d . 1 1 O O2 0.39925(5) 0.69845(18) 0.42131(7) 0.0374(3) Uani d . 1 1 O O3 0.5000 0.8767(2) 0.2500 0.0358(3) Uani d S 1 2 N N1 0.37706(8) 0.3841(3) 0.53985(10) 0.0451(3) Uani d . 1 1 H H1A 0.3429(12) 0.260(3) 0.5619(13) 0.054(4) Uiso d . 1 1 H H1B 0.4360(12) 0.398(3) 0.5657(13) 0.051(4) Uiso d . 1 1 C C1 0.33731(8) 0.5279(2) 0.45456(10) 0.0333(3) Uani d . 1 1 C C2 0.35837(8) 0.8634(3) 0.33006(11) 0.0392(3) Uani d . 1 1 H H2A 0.3086 0.9708 0.3518 0.047 Uiso calc R 1 1 H H2B 0.3306 0.7572 0.2678 0.047 Uiso calc R 1 1 C C3 0.43501(9) 1.0321(3) 0.29804(11) 0.0379(3) Uani d . 1 1 H H3A 0.4071 1.1628 0.2455 0.045 Uiso calc R 1 1 H H3B 0.4683 1.1206 0.3628 0.045 Uiso calc R 1 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 O1 0.0300(5) 0.0575(6) 0.0477(6) -0.0091(4) -0.0029(4) 0.0107(5) O2 0.0266(4) 0.0479(5) 0.0365(5) -0.0039(4) 0.0020(4) 0.0091(4) O3 0.0363(6) 0.0328(6) 0.0403(7) 0.000 0.0128(5) 0.000 N1 0.0301(6) 0.0570(8) 0.0464(7) -0.0046(5) 0.0007(5) 0.0168(6) C1 0.0277(6) 0.0402(7) 0.0321(6) -0.0025(5) 0.0055(5) -0.0009(5) C2 0.0309(6) 0.0480(8) 0.0386(7) 0.0031(5) 0.0050(5) 0.0089(6) C3 0.0376(7) 0.0365(7) 0.0414(7) 0.0034(5) 0.0119(6) 0.0027(5) 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 C1 O2 C2 . 114.33(9) C3 O3 C3 2_655 111.63(13) C1 N1 H1A . 117.6(10) C1 N1 H1B . 121.0(11) H1A N1 H1B . 120.9(15) O1 C1 N1 . 125.25(12) O1 C1 O2 . 122.31(11) N1 C1 O2 . 112.44(11) O2 C2 C3 . 108.85(10) O2 C2 H2A . 109.9 C3 C2 H2A . 109.9 O2 C2 H2B . 109.9 C3 C2 H2B . 109.9 H2A C2 H2B . 108.3 O3 C3 C2 . 109.65(11) O3 C3 H3A . 109.7 C2 C3 H3A . 109.7 O3 C3 H3B . 109.7 C2 C3 H3B . 109.7 H3A C3 H3B . 108.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance O1 C1 . 1.2191(15) O2 C1 . 1.3543(15) O2 C2 . 1.4494(15) O3 C3 . 1.4228(14) O3 C3 2_655 1.4228(14) N1 C1 . 1.3305(17) N1 H1A . 0.872(18) N1 H1B . 0.852(17) C2 C3 . 1.4973(18) C2 H2A . 0.9700 C2 H2B . 0.9700 C3 H3A . 0.9700 C3 H3B . 0.9700 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 H1A O1 7_556 0.872(18) 2.046(18) 2.9086(17) 169.9(14) N1 H1B O2 5_666 0.852(17) 2.381(17) 3.1763(17) 155.6(14) 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_site_symmetry_1 _geom_torsion C2 O2 C1 O1 . 1.42(17) C2 O2 C1 N1 . -178.66(11) C1 O2 C2 C3 . -177.18(10) C3 O3 C3 C2 2_655 170.41(12) O2 C2 C3 O3 . 68.67(13)