#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202209.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_2202209 loop_ _publ_author_name 'Lu, Liping' 'Zhou Chengyong' 'Zhang, Guocai' 'Zhu, Miaoli' 'Yang, Pin' _publ_section_title ; 1-Methyl-4-nitro-2-(trichloroacetyl)pyrrole ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o478 _journal_page_last o479 _journal_paper_doi 10.1107/S1600536803005555 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C7 H5 Cl3 N2 O3' _chemical_formula_moiety 'C7 H5 Cl3 N2 O3' _chemical_formula_sum 'C7 H5 Cl3 N2 O3' _chemical_formula_weight 271.48 _chemical_name_common 1-Methyl-2-trichloroacetyl-4-nitropyrrole _chemical_name_systematic ; 1-Methyl-4-nitro-2-(trichloroacetyl)pyrrole ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 11.590(4) _cell_length_b 10.603(3) _cell_length_c 16.935(5) _cell_measurement_reflns_used 3073 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 27.19 _cell_measurement_theta_min 2.86 _cell_volume 2081.1(11) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material SHELXTL/PC _computing_structure_refinement 'SHELXL97 (Sheldrick, 2000)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2000)' _diffrn_ambient_temperature 193(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 1K CCD area-detector' _diffrn_measurement_method \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 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7949 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.41 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.867 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.733 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1088 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.331 _refine_diff_density_min -0.189 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 1837 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0465 _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^)+(0.0553P)^2^+0.8439P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1079 _refine_ls_wR_factor_ref 0.1124 _reflns_number_gt 1574 _reflns_number_total 1837 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6144.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 'Orthorhombic' changed to 'orthorhombic' 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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 2081.2(11) _cod_database_code 2202209 _cod_database_fobs_code 2202209 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O2 0.2386(2) -0.0288(2) 1.05488(14) 0.0763(7) Uani d . 1 . . O Cl1 0.43332(7) 0.09579(9) 0.70167(5) 0.0686(3) Uani d . 1 . . Cl Cl2 0.66325(7) 0.18290(9) 0.67657(5) 0.0706(3) Uani d . 1 . . Cl Cl3 0.62763(9) -0.05161(8) 0.75825(6) 0.0760(3) Uani d . 1 . . Cl C3 0.4904(2) 0.1345(2) 0.88368(15) 0.0399(6) Uani d . 1 . . C C4 0.4192(2) 0.0315(3) 0.88783(16) 0.0434(6) Uani d . 1 . . C H4 0.4102 -0.0310 0.8498 0.052 Uiso calc R 1 . . H N2 0.2791(2) -0.0471(2) 0.98913(16) 0.0556(7) Uani d . 1 . . N N1 0.47657(19) 0.2036(2) 0.95299(13) 0.0434(5) Uani d . 1 . . N C2 0.5735(2) 0.1735(3) 0.82389(17) 0.0467(7) Uani d . 1 . . C C5 0.3628(2) 0.0394(3) 0.96037(17) 0.0429(6) Uani d . 1 . . C O1 0.6432(2) 0.2557(2) 0.83321(14) 0.0774(7) Uani d . 1 . . O C1 0.5730(2) 0.1024(3) 0.74347(17) 0.0501(7) Uani d . 1 . . C C6 0.3992(2) 0.1462(3) 0.99869(17) 0.0454(7) Uani d . 1 . . C H6 0.3743 0.1737 1.0480 0.054 Uiso calc R 1 . . H C7 0.5283(3) 0.3257(3) 0.97263(19) 0.0615(8) Uani d . 1 . . C H7A 0.4935 0.3580 1.0199 0.092 Uiso calc R 1 . . H H7B 0.5155 0.3838 0.9300 0.092 Uiso calc R 1 . . H H7C 0.6097 0.3153 0.9808 0.092 Uiso calc R 1 . . H O3 0.2513(2) -0.1352(2) 0.94712(16) 0.0864(8) 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 O2 0.0714(16) 0.0900(18) 0.0675(15) 0.0037(13) 0.0308(13) 0.0150(13) Cl1 0.0538(5) 0.1008(7) 0.0513(5) -0.0077(4) -0.0042(4) -0.0021(4) Cl2 0.0628(5) 0.0948(7) 0.0542(5) -0.0062(4) 0.0178(4) 0.0103(4) Cl3 0.0930(7) 0.0576(5) 0.0775(6) 0.0200(5) 0.0132(5) -0.0045(4) C3 0.0419(14) 0.0399(14) 0.0379(14) 0.0022(11) 0.0001(11) 0.0022(11) C4 0.0428(15) 0.0405(15) 0.0468(16) 0.0038(12) 0.0007(12) 0.0009(12) N2 0.0477(15) 0.0505(15) 0.0686(18) 0.0073(12) 0.0147(13) 0.0145(14) N1 0.0477(13) 0.0400(12) 0.0424(12) 0.0035(10) -0.0021(10) 0.0005(10) C2 0.0483(16) 0.0423(15) 0.0493(17) 0.0006(13) 0.0019(13) 0.0024(13) C5 0.0368(14) 0.0433(15) 0.0486(16) 0.0065(12) 0.0026(12) 0.0117(13) O1 0.0844(16) 0.0751(16) 0.0727(15) -0.0386(14) 0.0210(13) -0.0142(13) C1 0.0455(16) 0.0566(18) 0.0481(17) -0.0007(14) 0.0067(13) 0.0046(14) C6 0.0476(16) 0.0489(16) 0.0396(15) 0.0094(13) 0.0033(12) 0.0049(13) C7 0.076(2) 0.0511(18) 0.0573(19) -0.0070(16) -0.0014(17) -0.0099(14) O3 0.0916(19) 0.0610(15) 0.107(2) -0.0274(14) 0.0374(16) -0.0118(15) 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' 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_publ_flag C4 C3 N1 107.8(2) y C4 C3 C2 131.3(2) y N1 C3 C2 120.8(2) y C3 C4 C5 106.3(2) y C3 C4 H4 126.9 ? C5 C4 H4 126.9 ? O3 N2 O2 123.5(3) ? O3 N2 C5 118.4(3) y O2 N2 C5 118.1(3) y C6 N1 C3 109.1(2) y C6 N1 C7 123.2(2) ? C3 N1 C7 127.5(2) ? O1 C2 C3 124.0(3) y O1 C2 C1 118.0(3) y C3 C2 C1 118.0(2) y C6 C5 C4 108.8(2) y C6 C5 N2 125.5(3) y C4 C5 N2 125.7(3) y C2 C1 Cl2 109.0(2) y C2 C1 Cl1 111.87(19) y Cl2 C1 Cl1 107.77(16) y C2 C1 Cl3 108.8(2) y Cl2 C1 Cl3 109.01(16) y Cl1 C1 Cl3 110.32(17) y N1 C6 C5 108.0(2) y N1 C6 H6 126.0 ? C5 C6 H6 126.0 ? N1 C7 H7A 109.5 ? N1 C7 H7B 109.5 ? H7A C7 H7B 109.5 ? N1 C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? 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 O2 N2 . 1.224(3) y Cl1 C1 . 1.769(3) y Cl2 C1 . 1.762(3) y Cl3 C1 . 1.769(3) y C3 C4 . 1.371(4) y C3 N1 . 1.393(3) y C3 C2 . 1.457(4) y C4 C5 . 1.394(4) y C4 H4 . 0.9300 ? N2 O3 . 1.217(3) y N2 C5 . 1.421(4) y N1 C6 . 1.331(3) y N1 C7 . 1.465(4) y C2 O1 . 1.199(3) y C2 C1 . 1.556(4) y C5 C6 . 1.372(4) y C6 H6 . 0.9300 ? C7 H7A . 0.9600 ? C7 H7B . 0.9600 ? C7 H7C . 0.9600 ? 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 _geom_torsion_publ_flag N1 C3 C4 C5 -0.2(3) y C2 C3 C4 C5 177.0(3) y C4 C3 N1 C6 -0.2(3) y C2 C3 N1 C6 -177.8(2) y C4 C3 N1 C7 -175.1(3) y C2 C3 N1 C7 7.3(4) y C4 C3 C2 O1 -168.0(3) y N1 C3 C2 O1 9.0(4) y C4 C3 C2 C1 10.9(4) y N1 C3 C2 C1 -172.1(2) y C3 C4 C5 C6 0.5(3) y C3 C4 C5 N2 179.0(2) y O3 N2 C5 C6 176.7(3) ? O2 N2 C5 C6 -3.0(4) ? O3 N2 C5 C4 -1.5(4) ? O2 N2 C5 C4 178.8(3) ? O1 C2 C1 Cl2 -10.6(3) ? C3 C2 C1 Cl2 170.4(2) ? O1 C2 C1 Cl1 -129.7(3) ? C3 C2 C1 Cl1 51.3(3) ? O1 C2 C1 Cl3 108.2(3) ? C3 C2 C1 Cl3 -70.8(3) ? C3 N1 C6 C5 0.5(3) y C7 N1 C6 C5 175.6(2) ? C4 C5 C6 N1 -0.6(3) ? N2 C5 C6 N1 -179.1(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2040714 2 PubChem 2759966