#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/44/2204404.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_2204404 loop_ _publ_author_name 'Zhang, Ying' 'Feng, Tian-Yang' _publ_section_title ; 2-Chloro-N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1717 _journal_page_last o1718 _journal_paper_doi 10.1107/S1600536804021646 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C8 H5 Cl2 F N2 O3' _chemical_formula_moiety 'C8 H5 Cl2 F N2 O3' _chemical_formula_sum 'C8 H5 Cl2 F N2 O3' _chemical_formula_weight 267.04 _chemical_name_systematic ; 2-Chloro-N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.139(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.193(3) _cell_length_b 6.4489(19) _cell_length_c 14.427(4) _cell_measurement_reflns_used 860 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.16 _cell_measurement_theta_min 3.46 _cell_volume 1039.8(5) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 5701 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 2.83 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.631 _exptl_absorpt_correction_T_max 0.881 _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.362 _refine_diff_density_min -0.397 _refine_ls_extinction_coef 0.031(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 169 _refine_ls_number_reflns 2104 _refine_ls_number_restraints 31 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0348 _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^)+(0.0468P)^2^+0.356P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.0952 _reflns_number_gt 1618 _reflns_number_total 2104 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6273.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2204404 _cod_database_fobs_code 2204404 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 Cl1 0.66307(5) 0.02654(9) -0.04980(4) 0.0540(2) Uani d . 1 A . Cl Cl2 0.43021(6) 0.86911(12) 0.30681(5) 0.0791(3) Uani d . 1 . . Cl F1 0.88359(12) 0.2647(2) -0.04761(10) 0.0651(4) Uani d . 1 . . F N1 0.54229(15) 0.6038(3) 0.17069(12) 0.0420(4) Uani d D 1 A . N H1 0.564(2) 0.713(2) 0.2000(14) 0.049(7) Uiso d D 1 . . H N2 0.77366(18) 0.8099(3) 0.15175(13) 0.0548(5) Uani d D 1 . . N O1 0.39531(16) 0.3590(3) 0.16375(14) 0.0745(6) Uani d . 1 A . O O2 0.7006(6) 0.8982(14) 0.1977(6) 0.070(2) Uani d PDU 0.81(3) A 1 O O3 0.8714(6) 0.887(2) 0.1370(9) 0.082(3) Uani d PDU 0.81(3) A 1 O O2' 0.7082(19) 0.919(5) 0.195(2) 0.047(7) Uani d PDU 0.19(3) A 2 O O3' 0.8826(8) 0.814(5) 0.170(2) 0.056(6) Uani d PDU 0.19(3) A 2 O C1 0.62743(16) 0.5200(3) 0.11420(13) 0.0354(4) Uani d . 1 . . C C2 0.73868(18) 0.6164(3) 0.10460(13) 0.0397(5) Uani d . 1 A . C C3 0.82427(18) 0.5318(4) 0.04992(15) 0.0461(5) Uani d . 1 . . C H3 0.8973 0.5981 0.0443 0.055 Uiso calc R 1 A . H C4 0.80003(18) 0.3507(3) 0.00464(15) 0.0441(5) Uani d . 1 A . C C5 0.69164(18) 0.2525(3) 0.01112(14) 0.0385(4) Uani d . 1 . . C C6 0.60614(17) 0.3368(3) 0.06539(14) 0.0398(5) Uani d . 1 A . C H6 0.5330 0.2699 0.0693 0.048 Uiso calc R 1 . . H C7 0.43841(19) 0.5167(3) 0.19534(16) 0.0459(5) Uani d . 1 . . C C8 0.3721(2) 0.6279(4) 0.26896(19) 0.0608(6) Uani d . 1 A . C H8A 0.3697 0.5374 0.3225 0.073 Uiso calc R 1 . . H H8B 0.2902 0.6490 0.2453 0.073 Uiso calc 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 Cl1 0.0578(4) 0.0441(3) 0.0615(4) -0.0068(2) 0.0171(3) -0.0143(3) Cl2 0.0689(4) 0.0858(5) 0.0841(5) -0.0030(4) 0.0173(4) -0.0426(4) F1 0.0521(8) 0.0658(9) 0.0807(10) -0.0050(6) 0.0323(7) -0.0137(8) N1 0.0426(9) 0.0394(10) 0.0446(10) -0.0029(8) 0.0076(8) -0.0066(8) N2 0.0555(12) 0.0588(12) 0.0500(11) -0.0181(10) 0.0030(10) -0.0120(10) O1 0.0591(10) 0.0637(11) 0.1042(15) -0.0211(9) 0.0378(10) -0.0294(11) O2 0.079(3) 0.059(3) 0.076(3) -0.022(2) 0.022(2) -0.029(3) O3 0.0690(19) 0.079(4) 0.099(4) -0.043(2) 0.019(2) -0.028(4) O2' 0.053(9) 0.039(8) 0.051(10) -0.010(6) 0.006(7) 0.000(7) O3' 0.050(6) 0.050(9) 0.069(9) -0.027(4) 0.000(5) -0.007(6) C1 0.0362(10) 0.0365(10) 0.0334(10) -0.0013(8) 0.0016(8) 0.0026(8) C2 0.0419(11) 0.0410(11) 0.0361(10) -0.0069(9) -0.0004(8) -0.0003(9) C3 0.0366(10) 0.0526(13) 0.0496(12) -0.0101(9) 0.0062(9) 0.0016(11) C4 0.0397(10) 0.0483(13) 0.0455(11) 0.0014(9) 0.0123(9) 0.0035(10) C5 0.0427(10) 0.0351(10) 0.0382(10) -0.0014(8) 0.0062(8) 0.0012(9) C6 0.0366(10) 0.0384(11) 0.0449(11) -0.0048(8) 0.0065(9) -0.0006(9) C7 0.0428(11) 0.0443(12) 0.0512(12) 0.0013(9) 0.0085(9) -0.0013(10) C8 0.0598(14) 0.0602(15) 0.0648(15) 0.0000(12) 0.0233(12) -0.0086(13) 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' F F 0.0171 0.0103 '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 C7 N1 C1 127.97(18) C7 N1 H1 115.8(16) C1 N1 H1 115.4(16) O2' N2 O2 8(2) O2' N2 O3 115.0(17) O2 N2 O3 122.2(4) O2' N2 O3' 119.8(12) O2 N2 O3' 123.9(10) O3 N2 O3' 31.9(11) O2' N2 C2 125.3(16) O2 N2 C2 118.6(5) O3 N2 C2 118.8(3) O3' N2 C2 110.7(10) C6 C1 N1 121.42(17) C6 C1 C2 117.02(18) N1 C1 C2 121.55(18) C3 C2 C1 121.74(19) C3 C2 N2 115.11(18) C1 C2 N2 123.15(18) C4 C3 C2 119.09(19) C4 C3 H3 120.5 C2 C3 H3 120.5 F1 C4 C3 119.66(18) F1 C4 C5 119.22(19) C3 C4 C5 121.12(19) C4 C5 C6 119.85(19) C4 C5 Cl1 119.63(16) C6 C5 Cl1 120.51(15) C5 C6 C1 121.17(18) C5 C6 H6 119.4 C1 C6 H6 119.4 O1 C7 N1 125.6(2) O1 C7 C8 117.7(2) N1 C7 C8 116.7(2) C7 C8 Cl2 116.77(17) C7 C8 H8A 108.1 Cl2 C8 H8A 108.1 C7 C8 H8B 108.1 Cl2 C8 H8B 108.1 H8A C8 H8B 107.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C5 1.722(2) Cl2 C8 1.761(3) F1 C4 1.352(2) N1 C7 1.356(3) N1 C1 1.396(3) N1 H1 0.849(10) N2 O2' 1.210(10) N2 O2 1.221(4) N2 O3 1.231(4) N2 O3' 1.233(9) N2 C2 1.465(3) O1 C7 1.204(3) C1 C6 1.389(3) C1 C2 1.405(3) C2 C3 1.386(3) C3 C4 1.358(3) C3 H3 0.9300 C4 C5 1.376(3) C5 C6 1.381(3) C6 H6 0.9300 C7 C8 1.510(3) C8 H8A 0.9700 C8 H8B 0.9700 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 Cl2 0.850(10) 2.42(2) 2.937(2) 120(2) N1 H1 O2 0.850(10) 1.94(2) 2.611(9) 135(2) N1 H1 O2' 0.850(10) 2.10(4) 2.766(4) 135(2) 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 C7 N1 C1 C6 8.3(3) C7 N1 C1 C2 -171.3(2) C6 C1 C2 C3 -0.8(3) N1 C1 C2 C3 178.81(19) C6 C1 C2 N2 180.00(18) N1 C1 C2 N2 -0.4(3) O2' N2 C2 C3 172(2) O2 N2 C2 C3 176.7(6) O3 N2 C2 C3 3.1(10) O3' N2 C2 C3 -31(2) O2' N2 C2 C1 -9(2) O2 N2 C2 C1 -4.1(6) O3 N2 C2 C1 -177.6(10) O3' N2 C2 C1 148(2) C1 C2 C3 C4 -0.2(3) N2 C2 C3 C4 179.09(19) C2 C3 C4 F1 -178.83(19) C2 C3 C4 C5 1.0(3) F1 C4 C5 C6 178.99(18) C3 C4 C5 C6 -0.9(3) F1 C4 C5 Cl1 -1.8(3) C3 C4 C5 Cl1 178.34(17) C4 C5 C6 C1 -0.2(3) Cl1 C5 C6 C1 -179.36(15) N1 C1 C6 C5 -178.65(18) C2 C1 C6 C5 1.0(3) C1 N1 C7 O1 -8.8(4) C1 N1 C7 C8 171.0(2) O1 C7 C8 Cl2 -174.7(2) N1 C7 C8 Cl2 5.5(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 71417060