#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206790.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_2206790 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Xiang Chao Zeng' _publ_section_title ; Ethyl (4-bromo-1H-pyrrole-2-carboxamido)acetate ; _journal_coeditor_code SJ6125 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o2958 _journal_page_last o2960 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C9 H11 Br N2 O3' _chemical_formula_moiety 'C9 H11 Br N2 O3' _chemical_formula_sum 'C9 H11 Br N2 O3' _chemical_formula_weight 275.11 _chemical_melting_point 181 _chemical_name_systematic ; Ethyl (4-bromo-1H-pyrrole-2-carboxamido)acetate ; _symmetry_cell_setting monoclinic _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 107.843(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.944(2) _cell_length_b 5.0501(8) _cell_length_c 16.264(3) _cell_measurement_reflns_used 1926 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.32 _cell_measurement_theta_min 2.58 _cell_volume 1168.4(3) _computing_cell_refinement 'SAINT-Plus (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT-Plus _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Bruker, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker SMART 1K 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 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 6732 _diffrn_reflns_theta_full 27.02 _diffrn_reflns_theta_max 27.02 _diffrn_reflns_theta_min 2.58 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.508 _exptl_absorpt_correction_T_max 0.303 _exptl_absorpt_correction_T_min 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.564 _exptl_crystal_description Block _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.34 _refine_diff_density_max 0.462 _refine_diff_density_min -0.337 _refine_ls_extinction_coef 0.0053(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 138 _refine_ls_number_reflns 2550 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0366 _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^)+(0.0463P)^2^+0.5034P] where P= (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0936 _refine_ls_wR_factor_ref 0.1102 _reflns_number_gt 1562 _reflns_number_total 2550 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sj6125.cif 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_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_ _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 Br1 0.09732(2) 0.27459(10) -0.00515(3) 0.1090(3) Uani d . 1 Br C1 0.2661(2) 0.0278(6) -0.01976(18) 0.0576(7) Uani d . 1 C H1 0.2343 -0.1065 -0.0562 0.069 Uiso calc R 1 H C2 0.2264(2) 0.2253(6) 0.01464(19) 0.0595(8) Uani d . 1 C C3 0.29750(18) 0.3852(6) 0.06599(17) 0.0533(7) Uani d . 1 C H3 0.2901 0.5329 0.0975 0.064 Uiso calc R 1 H C4 0.38099(19) 0.2819(5) 0.06104(16) 0.0432(6) Uani d . 1 C C5 0.47844(18) 0.3672(5) 0.09482(15) 0.0429(6) Uani d . 1 C C6 0.5911(2) 0.6769(5) 0.17947(18) 0.0507(6) Uani d . 1 C H6A 0.5910 0.8386 0.2117 0.061 Uiso calc R 1 H H6B 0.6116 0.7213 0.1300 0.061 Uiso calc R 1 H C7 0.65965(18) 0.4850(5) 0.23595(17) 0.0471(6) Uani d . 1 C C8 0.8196(3) 0.3596(12) 0.2849(3) 0.1242(18) Uani d . 1 C H8A 0.8313 0.3953 0.3459 0.149 Uiso calc R 1 H H8B 0.8004 0.1761 0.2740 0.149 Uiso calc R 1 H C9 0.9024(4) 0.406(2) 0.2617(4) 0.220(4) Uani d . 1 C H9A 0.8872 0.4080 0.2000 0.330 Uiso calc R 1 H H9B 0.9471 0.2675 0.2850 0.330 Uiso calc R 1 H H9C 0.9290 0.5734 0.2846 0.330 Uiso calc R 1 H N1 0.36012(15) 0.0636(4) 0.00885(13) 0.0483(5) Uani d . 1 N H1A 0.4007 -0.0358 -0.0038 0.058 Uiso calc R 1 H N2 0.49743(14) 0.5732(4) 0.14961(13) 0.0479(5) Uani d . 1 N H2 0.4536 0.6426 0.1667 0.057 Uiso calc R 1 H O1 0.54214(13) 0.2578(3) 0.07369(12) 0.0532(5) Uani d . 1 O O2 0.64098(14) 0.3132(4) 0.27816(13) 0.0599(5) Uani d . 1 O O3 0.74556(14) 0.5333(5) 0.23359(15) 0.0795(7) 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 0.0461(2) 0.1456(5) 0.1290(4) 0.0081(2) 0.0175(2) -0.0253(3) C1 0.0562(17) 0.0594(18) 0.0543(16) -0.0034(14) 0.0127(13) -0.0054(14) C2 0.0437(15) 0.071(2) 0.0627(17) 0.0068(14) 0.0154(14) -0.0036(15) C3 0.0513(16) 0.0545(17) 0.0564(16) 0.0092(13) 0.0197(13) -0.0066(14) C4 0.0519(14) 0.0391(14) 0.0412(13) 0.0058(11) 0.0181(11) 0.0002(11) C5 0.0511(15) 0.0393(14) 0.0410(13) 0.0086(11) 0.0180(11) 0.0034(11) C6 0.0591(17) 0.0396(14) 0.0571(16) -0.0015(12) 0.0235(14) 0.0010(12) C7 0.0486(15) 0.0480(15) 0.0487(14) -0.0026(12) 0.0210(12) 0.0006(13) C8 0.054(2) 0.186(5) 0.132(4) 0.025(3) 0.028(2) 0.077(4) C9 0.084(4) 0.408(13) 0.175(6) 0.080(6) 0.049(4) 0.081(7) N1 0.0530(13) 0.0458(13) 0.0489(12) 0.0075(10) 0.0196(10) -0.0044(10) N2 0.0466(12) 0.0456(13) 0.0548(12) 0.0053(10) 0.0205(10) -0.0080(11) O1 0.0516(11) 0.0530(11) 0.0604(11) 0.0087(8) 0.0254(9) -0.0088(9) O2 0.0604(12) 0.0609(12) 0.0599(11) -0.0068(10) 0.0205(10) 0.0187(10) O3 0.0510(12) 0.1006(17) 0.0935(16) 0.0035(11) 0.0320(11) 0.0356(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C2 1.872(3) C1 N1 1.350(3) C1 C2 1.365(4) C1 H1 0.9300 C2 C3 1.391(4) C3 C4 1.377(4) C3 H3 0.9300 C4 N1 1.368(3) C4 C5 1.455(4) C5 O1 1.237(3) C5 N2 1.343(3) C6 N2 1.433(3) C6 C7 1.502(4) C6 H6A 0.9700 C6 H6B 0.9700 C7 O2 1.191(3) C7 O3 1.319(3) C8 C9 1.420(6) C8 O3 1.457(4) C8 H8A 0.9700 C8 H8B 0.9700 C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 N1 H1A 0.8600 N2 H2 0.8600 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C2 107.4(2) N1 C1 H1 126.3 C2 C1 H1 126.3 C1 C2 C3 108.8(3) C1 C2 Br1 125.5(2) C3 C2 Br1 125.7(2) C4 C3 C2 106.5(2) C4 C3 H3 126.7 C2 C3 H3 126.7 N1 C4 C3 107.6(2) N1 C4 C5 119.0(2) C3 C4 C5 133.3(2) O1 C5 N2 120.4(2) O1 C5 C4 122.0(2) N2 C5 C4 117.6(2) N2 C6 C7 112.6(2) N2 C6 H6A 109.1 C7 C6 H6A 109.1 N2 C6 H6B 109.1 C7 C6 H6B 109.1 H6A C6 H6B 107.8 O2 C7 O3 123.6(3) O2 C7 C6 125.9(2) O3 C7 C6 110.5(2) C9 C8 O3 108.6(4) C9 C8 H8A 110.0 O3 C8 H8A 110.0 C9 C8 H8B 110.0 O3 C8 H8B 110.0 H8A C8 H8B 108.3 C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C1 N1 C4 109.7(2) C1 N1 H1A 125.1 C4 N1 H1A 125.1 C5 N2 C6 119.6(2) C5 N2 H2 120.2 C6 N2 H2 120.2 C7 O3 C8 116.5(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 N1 C1 C2 C3 -0.4(3) N1 C1 C2 Br1 179.0(2) C1 C2 C3 C4 0.7(3) Br1 C2 C3 C4 -178.7(2) C2 C3 C4 N1 -0.8(3) C2 C3 C4 C5 175.3(3) N1 C4 C5 O1 4.4(4) C3 C4 C5 O1 -171.3(3) N1 C4 C5 N2 -176.4(2) C3 C4 C5 N2 7.8(4) N2 C6 C7 O2 -25.9(4) N2 C6 C7 O3 154.7(2) C2 C1 N1 C4 -0.1(3) C3 C4 N1 C1 0.5(3) C5 C4 N1 C1 -176.2(2) O1 C5 N2 C6 3.9(4) C4 C5 N2 C6 -175.3(2) C7 C6 N2 C5 -66.7(3) O2 C7 O3 C8 1.3(5) C6 C7 O3 C8 -179.3(3) C9 C8 O3 C7 168.7(5) 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 3_655 0.86 1.97 2.788(3) 159 N2 H2 O2 2_655 0.86 2.08 2.935(3) 174