#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2205225.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_2205225 loop_ _publ_author_name 'Hao, Jing-Jun' 'Xu, Hu' 'Song, Hai-Bing' 'Wang, You-Ming' 'Li, Zheng-Ming' _publ_section_title ; 3-(Imidazolidin-2-ylidene)-6-methyl-3,4,5,6-tetrahydro-2H-pyran-2,4-dione ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o749 _journal_page_last o750 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C9 H12 N2 O3' _chemical_formula_moiety 'C9 H12 N2 O3' _chemical_formula_sum 'C9 H12 N2 O3' _chemical_formula_weight 196.21 _chemical_melting_point 448.5 _chemical_name_systematic ; 3-(Imidazolidin-2-ylidene)-6-methyl-3,4,5,6-tetrahydro-2H-pyran-2,4-dione ; _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 92.866(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.195(2) _cell_length_b 7.106(2) _cell_length_c 9.131(3) _cell_measurement_reflns_used 920 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.80 _cell_measurement_theta_min 2.23 _cell_volume 466.3(2) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(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 MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 2713 _diffrn_reflns_theta_full 26.42 _diffrn_reflns_theta_max 26.42 _diffrn_reflns_theta_min 2.23 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.160 _refine_diff_density_min -0.145 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 98 _refine_ls_number_reflns 1030 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0446 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.065P)^2^+0.0755P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1212 _refine_ls_wR_factor_ref 0.1377 _reflns_number_gt 701 _reflns_number_total 1030 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6397.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/m' _cod_database_code 2205225 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x,1/2-y,z -x,-1/2+y,-z 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 0.4535(2) 0.7500 -0.02228(17) 0.0618(6) Uani d S 1 O O2 0.7217(2) 0.7500 0.09917(18) 0.0685(6) Uani d S 1 O O3 0.1694(2) 0.7500 0.3511(2) 0.0995(9) Uani d S 1 O N1 0.7472(3) 0.7500 0.3931(2) 0.0679(7) Uani d SD 1 N H1A 0.819(3) 0.7500 0.320(2) 0.081 Uiso d SD 1 H N2 0.4916(3) 0.7500 0.5059(2) 0.0606(6) Uani d SD 1 N H2A 0.3710(14) 0.7500 0.503(3) 0.073 Uiso d SD 1 H C1 0.1778(5) 0.728(6) -0.1748(4) 0.089(6) Uani d P 0.50 C H1B 0.0495 0.6900 -0.1795 0.134 Uiso d PR 0.50 H H1C 0.1871 0.8564 -0.2053 0.134 Uiso d PR 0.50 H H1D 0.2463 0.6491 -0.2385 0.134 Uiso d PR 0.50 H C2 0.2568(4) 0.6922(5) -0.0199(4) 0.0554(11) Uani d P 0.50 C H2B 0.2472 0.5615 0.0053 0.067 Uiso d PR 0.50 H C3 0.1683(4) 0.8118(5) 0.0907(4) 0.0558(11) Uani d P 0.50 C H3A 0.0362 0.7918 0.0891 0.067 Uiso d PR 0.50 H H3B 0.1922 0.9423 0.0721 0.067 Uiso d PR 0.50 H C4 0.2617(3) 0.7500 0.2400(3) 0.0716(9) Uani d S 1 C C5 0.4574(3) 0.7500 0.2413(2) 0.0434(6) Uani d S 1 C C6 0.5525(3) 0.7500 0.1066(3) 0.0493(6) Uani d S 1 C C7 0.5646(3) 0.7500 0.3762(2) 0.0461(6) Uani d S 1 C C8 0.8119(4) 0.7500 0.5456(3) 0.0709(8) Uani d S 1 C H8A 0.8846 0.8601 0.5696 0.085 Uiso d R 1 H C9 0.6320(4) 0.7500 0.6250(3) 0.0623(7) Uani d S 1 C H9A 0.6222 0.8600 0.6851 0.075 Uiso d R 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 0.0403(9) 0.1040(15) 0.0408(10) 0.000 0.0007(7) 0.000 O2 0.0322(9) 0.1230(17) 0.0507(11) 0.000 0.0066(7) 0.000 O3 0.0420(10) 0.200(3) 0.0577(12) 0.000 0.0184(9) 0.000 N1 0.0425(11) 0.120(2) 0.0410(12) 0.000 -0.0010(9) 0.000 N2 0.0522(12) 0.0878(16) 0.0423(11) 0.000 0.0080(9) 0.000 C1 0.0626(19) 0.149(17) 0.0538(18) -0.008(5) -0.0168(15) 0.016(7) C2 0.0445(16) 0.071(3) 0.0506(18) -0.0054(14) -0.0044(13) 0.0028(14) C3 0.0322(14) 0.071(3) 0.064(2) 0.0007(13) -0.0021(14) 0.0022(15) C4 0.0384(13) 0.124(3) 0.0529(16) 0.000 0.0087(12) 0.000 C5 0.0351(12) 0.0530(14) 0.0423(12) 0.000 0.0046(9) 0.000 C6 0.0372(12) 0.0667(16) 0.0441(13) 0.000 0.0026(9) 0.000 C7 0.0448(12) 0.0510(14) 0.0430(13) 0.000 0.0063(10) 0.000 C8 0.0628(17) 0.100(2) 0.0483(15) 0.000 -0.0098(13) 0.000 C9 0.0741(18) 0.0703(17) 0.0420(13) 0.000 -0.0022(12) 0.000 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 C6 O1 C2 116.97(19) C7 N1 C8 112.6(2) C7 N1 H1A 123(2) C8 N1 H1A 124(2) C7 N2 C9 112.4(2) C7 N2 H2A 114.6(19) C9 N2 H2A 133.1(19) C2 C1 H1B 108.0 C2 C1 H1C 113.6 H1B C1 H1C 109.5 C2 C1 H1D 106.7 H1B C1 H1D 109.5 H1C C1 H1D 109.5 C3 C2 O1 107.1(2) O1 C2 C3 107.1(2) O1 C2 C1 104.8(6) C3 C2 C1 112.6(12) C3 C2 H2B 110.6 O1 C2 H2B 110.7 C1 C2 H2B 110.9 C2 C3 C4 104.7(2) C2 C3 H3A 111.2 C4 C3 H3A 110.9 C2 C3 H3B 110.2 C4 C3 H3B 110.8 H3A C3 H3B 109.0 O3 C4 C5 124.7(2) O3 C4 C3 119.5(2) C5 C4 C3 113.3(2) C4 C5 C7 120.4(2) C4 C5 C6 120.8(2) C7 C5 C6 118.8(2) O2 C6 O1 115.9(2) O2 C6 C5 124.5(2) O1 C6 C5 119.7(2) N1 C7 N2 109.6(2) N1 C7 C5 126.7(2) N2 C7 C5 123.7(2) N1 C8 C9 102.7(2) N1 C8 H8A 111.4 C9 C8 H8A 111.1 N2 C9 C8 102.8(2) N2 C9 H9A 111.2 C8 C9 H9A 111.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C6 1.345(3) O1 C2 1.475(3) O2 C6 1.223(3) O3 C4 1.240(3) N1 C7 1.315(3) N1 C8 1.446(3) N2 C7 1.319(3) N2 C9 1.447(3) C1 H1B 0.960 C1 H1C 0.960 C1 H1D 0.960 C1 C2 1.519(8) C2 C3 1.487(4) C2 H2B 0.960 C3 H3A 0.960 C3 H3B 0.9599 C4 C5 1.408(3) C4 C3 1.553(4) C5 C7 1.421(3) C5 C6 1.436(3) C8 C9 1.515(4) C8 H8A 0.960 C9 H9A 0.960 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 O2 . 0.864(10) 2.10(3) 2.681(3) 124(2) N2 H2A O3 . 0.867(10) 1.96(2) 2.655(3) 137(3) N1 H1A O3 1_655 0.864(10) 2.52(3) 3.081(3) 123(2)