#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202395.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_2202395 loop_ _publ_author_name 'Kraus, George A.' 'Choudhury, Prabir K.' 'Ellern, Arkady' _publ_section_title ; Methyl 6-bromo-2,3-dihydro-2-methylimidazo[2,1-b]oxazole-5-carboxylate ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1735 _journal_page_last o1737 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C8 H9 Br N2 O3' _chemical_formula_moiety 'C8 H9 Br N2 O3' _chemical_formula_sum 'C8 H9 Br N2 O3' _chemical_formula_weight 261.08 _chemical_name_systematic ; Methyl 6-bromo-2,3-dihydro-2-methylimidazo[2,1-b]oxazole-5-carboxylate ; _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 90.614(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.1338(13) _cell_length_b 13.981(3) _cell_length_c 9.4670(15) _cell_measurement_reflns_used 684 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.06 _cell_measurement_theta_min 2.60 _cell_volume 944.2(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.841 _diffrn_measurement_device_type 'Bruker SMART1000 CCD' _diffrn_measurement_method \f _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 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0487 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3396 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 28.18 _diffrn_reflns_theta_min 2.60 _exptl_absorpt_coefficient_mu 4.336 _exptl_absorpt_correction_T_max 0.676 _exptl_absorpt_correction_T_min 0.402 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS in SAINT; Bruker, 2002)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.837 _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.09 _refine_diff_density_max 1.098 _refine_diff_density_min -0.642 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1958 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0402 _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^)+(0.0495P)^2^+1.5689P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1042 _refine_ls_wR_factor_ref 0.1071 _reflns_number_gt 1701 _reflns_number_total 1958 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt6366.cif _[local]_cod_data_source_block 2 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 944.1(3) _cod_database_code 2202395 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Br1 0.83195(5) 0.33411(2) 0.74002(4) 0.02667(16) Uani d . 1 . . Br C1 0.7659(5) 0.4528(2) 0.6625(4) 0.0214(7) Uani d . 1 . . C C2 0.6614(6) 0.5914(3) 0.6605(4) 0.0275(8) Uani d . 1 . . C C3 0.5779(7) 0.7259(3) 0.5410(4) 0.0367(10) Uani d . 1 . . C H3A 0.4413 0.7281 0.5163 0.044 Uiso calc R 1 . . H C4 0.6507(10) 0.8237(3) 0.5476(5) 0.0534(16) Uani d . 1 . . C H4A 0.5784 0.8608 0.6159 0.080 Uiso calc R 1 . . H H4B 0.6397 0.8535 0.4542 0.080 Uiso calc R 1 . . H H4C 0.7828 0.8223 0.5771 0.080 Uiso calc R 1 . . H C5 0.6776(6) 0.6578(2) 0.4375(4) 0.0245(8) Uani d . 1 . . C H5A 0.6002 0.6456 0.3520 0.029 Uiso calc R 1 . . H H5B 0.8014 0.6830 0.4095 0.029 Uiso calc R 1 . . H C6 0.7700(5) 0.4798(2) 0.5226(4) 0.0206(7) Uani d . 1 . . C C7 0.8251(5) 0.4291(3) 0.3945(4) 0.0229(8) Uani d . 1 . . C C8 0.8236(7) 0.4353(3) 0.1447(4) 0.0376(10) Uani d . 1 . . C H8A 0.7858 0.4778 0.0671 0.056 Uiso calc R 1 . . H H8B 0.7560 0.3746 0.1363 0.056 Uiso calc R 1 . . H H8C 0.9588 0.4234 0.1401 0.056 Uiso calc R 1 . . H N1 0.6988(5) 0.5221(2) 0.7501(3) 0.0282(7) Uani d . 1 . . N N2 0.6959(5) 0.5722(2) 0.5253(3) 0.0229(7) Uani d . 1 . . N O1 0.6019(5) 0.6808(2) 0.6835(3) 0.0384(8) Uani d . 1 . . O O2 0.8995(4) 0.35153(19) 0.3932(3) 0.0307(7) Uani d . 1 . . O O3 0.7797(4) 0.48004(18) 0.2785(3) 0.0273(6) Uani d . 1 . . O 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 Br1 0.0290(3) 0.0226(2) 0.0284(2) 0.00023(14) -0.00267(16) 0.00721(14) C1 0.0222(18) 0.0204(16) 0.0214(17) -0.0007(14) -0.0010(15) 0.0044(14) C2 0.038(2) 0.0256(18) 0.0192(16) 0.0060(16) 0.0030(16) 0.0010(15) C3 0.053(3) 0.033(2) 0.0239(19) 0.009(2) 0.0046(19) 0.0055(17) C4 0.107(5) 0.031(2) 0.022(2) -0.003(3) 0.008(3) 0.0001(18) C5 0.036(2) 0.0222(17) 0.0156(16) 0.0044(15) 0.0025(16) 0.0032(13) C6 0.0188(18) 0.0196(16) 0.0233(17) -0.0021(13) -0.0038(14) 0.0013(14) C7 0.0229(19) 0.0235(18) 0.0222(17) -0.0070(14) -0.0043(15) -0.0009(14) C8 0.056(3) 0.035(2) 0.0213(19) 0.001(2) -0.0027(19) -0.0043(17) N1 0.038(2) 0.0261(16) 0.0203(15) 0.0040(14) 0.0036(14) 0.0041(12) N2 0.0300(17) 0.0241(15) 0.0147(13) 0.0016(13) 0.0005(13) 0.0010(12) O1 0.071(2) 0.0275(14) 0.0169(13) 0.0175(14) 0.0091(14) 0.0047(11) O2 0.0434(18) 0.0222(13) 0.0263(14) 0.0049(12) -0.0043(13) -0.0046(11) O3 0.0374(16) 0.0249(13) 0.0193(12) 0.0017(12) -0.0033(12) -0.0030(11) 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 Br1 C1 . 1.873(3) ? C1 N1 . 1.365(5) ? C1 C6 . 1.378(5) ? C2 N1 . 1.313(5) ? C2 N2 . 1.333(5) ? C2 O1 . 1.340(4) ? C3 C4 . 1.464(6) ? C3 O1 . 1.497(5) ? C3 C5 . 1.544(5) ? C3 H3A . 1.0000 ? C4 H4A . 0.9800 ? C4 H4B . 0.9800 ? C4 H4C . 0.9800 ? C5 N2 . 1.462(4) ? C5 H5A . 0.9900 ? C5 H5B . 0.9900 ? C6 N2 . 1.396(4) ? C6 C7 . 1.462(5) ? C7 O2 . 1.207(5) ? C7 O3 . 1.345(4) ? C8 O3 . 1.450(5) ? C8 H8A . 0.9800 ? C8 H8B . 0.9800 ? C8 H8C . 0.9800 ? 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' Br Br -0.2901 2.4595 '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 N1 C1 C6 113.7(3) N1 C1 Br1 118.6(3) C6 C1 Br1 127.7(3) N1 C2 N2 115.7(3) N1 C2 O1 130.3(3) N2 C2 O1 113.9(3) C4 C3 O1 108.5(4) C4 C3 C5 115.9(4) O1 C3 C5 105.3(3) C4 C3 H3A 109.0 O1 C3 H3A 109.0 C5 C3 H3A 109.0 C3 C4 H4A 109.5 C3 C4 H4B 109.5 H4A C4 H4B 109.5 C3 C4 H4C 109.5 H4A C4 H4C 109.5 H4B C4 H4C 109.5 N2 C5 C3 100.5(3) N2 C5 H5A 111.7 C3 C5 H5A 111.7 N2 C5 H5B 111.7 C3 C5 H5B 111.7 H5A C5 H5B 109.4 C1 C6 N2 102.9(3) C1 C6 C7 132.3(3) N2 C6 C7 124.7(3) O2 C7 O3 124.7(3) O2 C7 C6 124.4(4) O3 C7 C6 110.9(3) O3 C8 H8A 109.5 O3 C8 H8B 109.5 H8A C8 H8B 109.5 O3 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C2 N1 C1 101.6(3) C2 N2 C6 106.1(3) C2 N2 C5 111.4(3) C6 N2 C5 141.1(3) C2 O1 C3 106.2(3) C7 O3 C8 115.6(3) 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 C4 C3 C5 N2 135.5(4) O1 C3 C5 N2 15.6(4) N1 C1 C6 N2 -1.3(4) Br1 C1 C6 N2 176.4(3) N1 C1 C6 C7 -178.2(4) Br1 C1 C6 C7 -0.6(6) C1 C6 C7 O2 -8.2(7) N2 C6 C7 O2 175.4(4) C1 C6 C7 O3 171.0(4) N2 C6 C7 O3 -5.4(5) N2 C2 N1 C1 0.9(5) O1 C2 N1 C1 -175.6(5) C6 C1 N1 C2 0.3(5) Br1 C1 N1 C2 -177.5(3) N1 C2 N2 C6 -1.7(5) O1 C2 N2 C6 175.3(3) N1 C2 N2 C5 -171.2(4) O1 C2 N2 C5 5.8(5) C1 C6 N2 C2 1.7(4) C7 C6 N2 C2 178.9(4) C1 C6 N2 C5 166.0(5) C7 C6 N2 C5 -16.7(7) C3 C5 N2 C2 -13.5(5) C3 C5 N2 C6 -177.3(5) N1 C2 O1 C3 -178.2(5) N2 C2 O1 C3 5.3(5) C4 C3 O1 C2 -138.1(4) C5 C3 O1 C2 -13.4(5) O2 C7 O3 C8 0.8(6) C6 C7 O3 C8 -178.5(3)