#------------------------------------------------------------------------------ #$Date: 2016-01-27 06:18:51 +0200 (Wed, 27 Jan 2016) $ #$Revision: 175140 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/10/06/1100658.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1100658 loop_ _publ_author_name 'Doreswamy, Beeranahally H.' Basappa 'Mahendra, Madegowda' 'Mantelingu, Kempegowda' 'Anandalwar, Sridhar M.' 'Prasad, Javaregowda S.' 'Rangappa, Kanchugarakoppal S.' _publ_section_title ; Microwave-Assisted Synthesis and Crystal Structure of 2-Butyl-4-chloro-1H-imidazole-5-carboxaldehyde ; _journal_name_full ; Analytical Sciences: X-ray Structure Analysis Online ; _journal_page_first x31 _journal_page_last x32 _journal_paper_doi 10.2116/analscix.19.x31 _journal_volume 19 _journal_year 2003 _chemical_formula_sum 'C8 H11 Cl N2 O' _chemical_formula_weight 186.64 _space_group_IT_number 14 _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 _cell_angle_alpha 90.0000(10) _cell_angle_beta 101.94 _cell_angle_gamma 90.00(2) _cell_formula_units_Z 4 _cell_length_a 7.251 _cell_length_b 13.1950(10) _cell_length_c 9.8350(10) _cell_measurement_temperature 293(2) _cell_volume 920.62(12) _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.893 _diffrn_measured_fraction_theta_max 0.893 _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 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3617 _diffrn_reflns_theta_full 27.93 _diffrn_reflns_theta_max 27.93 _diffrn_reflns_theta_min 2.62 _exptl_absorpt_coefficient_mu 0.369 _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _refine_diff_density_max 0.657 _refine_diff_density_min -0.431 _refine_diff_density_rms 0.125 _refine_ls_extinction_coef 0.13(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 111 _refine_ls_number_reflns 1977 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0651 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1537P)^2^+0.1028P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1890 _refine_ls_wR_factor_ref 0.2167 _reflns_number_gt 1552 _reflns_number_total 1977 _reflns_threshold_expression >2sigma(I) _cod_cif_authors_sg_H-M P21/c _cod_database_code 1100658 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_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.76028(10) 0.54189(5) 0.15677(7) 0.0694(4) Uani 1 1 d . . . N6 N 0.9265(3) 0.70522(13) -0.1187(2) 0.0474(5) Uani 1 1 d . . . H6 H 0.9436 0.7217 -0.1998 0.057 Uiso 1 1 calc R . . N8 N 0.9356(3) 0.71213(13) 0.1070(2) 0.0505(5) Uani 1 1 d . . . C9 C 1.0789(4) 0.85854(15) 0.0039(3) 0.0558(6) Uani 1 1 d . . . H9A H 1.0060 0.9090 0.0415 0.067 Uiso 1 1 calc R . . H9B H 1.0855 0.8793 -0.0895 0.067 Uiso 1 1 calc R . . C2 C 0.8477(3) 0.62639(15) 0.0535(2) 0.0493(5) Uani 1 1 d . . . C3 C 0.8389(3) 0.61811(15) -0.0863(2) 0.0487(6) Uani 1 1 d . . . C7 C 0.9802(3) 0.75943(15) -0.0026(2) 0.0477(5) Uani 1 1 d . . . O5 O 0.7653(3) 0.54495(14) -0.3082(3) 0.0740(6) Uani 1 1 d . . . C11 C 1.4124(4) 0.7833(2) 0.0407(3) 0.0656(7) Uani 1 1 d . . . H11A H 1.5257 0.7754 0.1122 0.079 Uiso 1 1 calc R . . H11B H 1.3531 0.7173 0.0241 0.079 Uiso 1 1 calc R . . C4 C 0.7611(4) 0.54124(17) -0.1863(3) 0.0594(7) Uani 1 1 d . . . H4 H 0.7041 0.4853 -0.1547 0.071 Uiso 1 1 calc R . . C10 C 1.2784(4) 0.85528(18) 0.0933(3) 0.0609(7) Uani 1 1 d . . . H10A H 1.3311 0.9231 0.0982 0.073 Uiso 1 1 calc R . . H10B H 1.2707 0.8353 0.1869 0.073 Uiso 1 1 calc R . . C12 C 1.4663(5) 0.8192(3) -0.0901(4) 0.0828(9) Uani 1 1 d . . . H12A H 1.3555 0.8241 -0.1627 0.124 Uiso 1 1 calc R . . H12B H 1.5529 0.7720 -0.1170 0.124 Uiso 1 1 calc R . . H12C H 1.5250 0.8846 -0.0746 0.124 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0831(6) 0.0584(5) 0.0714(6) 0.0143(2) 0.0267(4) -0.0104(3) N6 0.0577(11) 0.0413(9) 0.0459(11) 0.0009(6) 0.0168(7) 0.0013(7) N8 0.0617(11) 0.0415(9) 0.0503(12) 0.0017(7) 0.0161(8) -0.0003(7) C9 0.0690(15) 0.0357(11) 0.0659(16) 0.0009(8) 0.0211(11) -0.0004(9) C2 0.0543(12) 0.0392(10) 0.0566(14) 0.0044(8) 0.0167(9) 0.0022(8) C3 0.0552(12) 0.0394(10) 0.0540(14) 0.0006(8) 0.0167(9) 0.0009(8) C7 0.0547(12) 0.0369(10) 0.0538(13) 0.0021(8) 0.0163(9) 0.0032(8) O5 0.0928(16) 0.0676(13) 0.0625(13) -0.0145(8) 0.0183(10) -0.0105(9) C11 0.0635(15) 0.0582(14) 0.0737(18) 0.0014(11) 0.0107(12) 0.0021(11) C4 0.0621(14) 0.0477(13) 0.0696(18) -0.0077(9) 0.0167(11) -0.0047(9) C10 0.0716(16) 0.0506(13) 0.0619(16) -0.0090(10) 0.0173(11) -0.0073(11) C12 0.083(2) 0.083(2) 0.087(2) -0.0026(16) 0.0290(16) 0.0158(16) 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N6 C3 108.33(19) . . ? C7 N8 C2 104.50(19) . . ? C7 C9 C10 112.9(2) . . ? N8 C2 C3 112.21(19) . . ? N8 C2 Cl1 121.11(18) . . ? C3 C2 Cl1 126.68(17) . . ? C2 C3 N6 103.75(18) . . ? C2 C3 C4 132.1(2) . . ? N6 C3 C4 124.1(2) . . ? N6 C7 N8 111.21(19) . . ? N6 C7 C9 124.1(2) . . ? N8 C7 C9 124.7(2) . . ? C12 C11 C10 113.1(2) . . ? O5 C4 C3 124.2(2) . . ? C11 C10 C9 114.6(2) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.715(2) . ? N6 C7 1.336(3) . ? N6 C3 1.382(3) . ? N8 C7 1.341(3) . ? N8 C2 1.350(3) . ? C9 C7 1.486(3) . ? C9 C10 1.530(4) . ? C2 C3 1.368(3) . ? C3 C4 1.444(3) . ? O5 C4 1.206(4) . ? C11 C12 1.497(5) . ? C11 C10 1.523(4) . ?