#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202545.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_2202545 loop_ _publ_author_name 'Maria Gdaniec' _publ_section_title ; 2,3,4,5,6-Pentafluorobenzamide ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1642 _journal_page_last o1644 _journal_paper_doi 10.1107/S1600536803021871 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C7 H2 F5 N1 O1' _chemical_formula_moiety 'C7 H2 F5 N1 O1' _chemical_formula_sum 'C7 H2 F5 N O' _chemical_formula_weight 211.10 _chemical_melting_point .146E-146 _chemical_name_systematic ; 2,3,4,5,6-Pentafluorobenzamide ; _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 difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.073(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.7305(11) _cell_length_b 6.1929(6) _cell_length_c 9.5856(10) _cell_measurement_reflns_used 2021 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 4 _cell_volume 744.07(13) _computing_cell_refinement 'CrysAlis CCD (Oxford Diffraction, 2000)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2000)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2000)' _computing_molecular_graphics 'Stereochemical Workstation (Siemens, 1989)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Kuma KM4CCD \k geometry' _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 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4010 _diffrn_reflns_theta_full 26.36 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_min 3.94 _diffrn_standards_decay_% none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.884 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.270 _refine_diff_density_min -0.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 135 _refine_ls_number_reflns 1517 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.128 _refine_ls_R_factor_all 0.0396 _refine_ls_R_factor_gt 0.0352 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.048P)^2^+0.2307P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.0904 _reflns_number_gt 1376 _reflns_number_total 1517 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cm6057.cif _cod_data_source_block I _cod_original_cell_volume 744.07(12) _cod_original_sg_symbol_Hall -P2ybc _cod_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum 'C7 H2 F5 N1 O1' _cod_database_code 2202545 _cod_database_fobs_code 2202545 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 F2 0.28574(7) 0.86929(14) -0.18731(9) 0.0237(2) Uani d . 1 . . F F3 0.44674(7) 0.59609(16) -0.19947(9) 0.0289(3) Uani d . 1 . . F F4 0.45317(8) 0.20334(16) -0.07058(10) 0.0315(3) Uani d . 1 . . F F5 0.29681(8) 0.08965(14) 0.07540(9) 0.0275(2) Uani d . 1 . . F F6 0.13508(7) 0.35968(14) 0.09104(9) 0.0245(2) Uani d . 1 . . F O1 0.09191(9) 0.80167(18) 0.09099(11) 0.0234(3) Uani d . 1 . . O N1 0.07115(11) 0.8917(2) -0.14075(13) 0.0222(3) Uani d . 1 . . N C1 0.20388(11) 0.6252(2) -0.04733(14) 0.0171(3) Uani d . 1 . . C C2 0.28496(12) 0.6771(2) -0.12198(15) 0.0185(3) Uani d . 1 . . C C3 0.36913(11) 0.5382(3) -0.12941(15) 0.0212(3) Uani d . 1 . . C C4 0.37288(12) 0.3396(2) -0.06351(16) 0.0220(3) Uani d . 1 . . C C5 0.29319(12) 0.2821(2) 0.01045(15) 0.0201(3) Uani d . 1 . . C C6 0.21048(12) 0.4238(2) 0.01839(14) 0.0186(3) Uani d . 1 . . C C7 0.11637(12) 0.7817(2) -0.02792(15) 0.0184(3) Uani d . 1 . . C H1 0.0887(15) 0.862(3) -0.224(2) 0.026(5) Uiso d . 1 . . H H2 0.0205(15) 0.986(3) -0.1306(18) 0.024(4) Uiso d . 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 F2 0.0285(5) 0.0240(5) 0.0199(4) -0.0036(4) 0.0081(4) 0.0037(4) F3 0.0212(5) 0.0415(6) 0.0269(5) -0.0033(4) 0.0119(4) -0.0030(4) F4 0.0261(5) 0.0360(6) 0.0326(5) 0.0117(4) 0.0058(4) -0.0058(4) F5 0.0390(5) 0.0207(5) 0.0222(5) 0.0053(4) 0.0038(4) 0.0031(4) F6 0.0280(5) 0.0247(5) 0.0237(5) -0.0030(4) 0.0122(4) 0.0028(4) O1 0.0291(6) 0.0279(6) 0.0150(5) 0.0074(5) 0.0083(4) 0.0020(4) N1 0.0267(7) 0.0263(7) 0.0152(6) 0.0083(6) 0.0080(5) 0.0024(5) C1 0.0184(7) 0.0200(7) 0.0130(6) -0.0007(6) 0.0028(5) -0.0021(5) C2 0.0222(7) 0.0198(7) 0.0138(6) -0.0028(6) 0.0037(5) -0.0012(5) C3 0.0183(7) 0.0305(8) 0.0157(7) -0.0039(6) 0.0053(5) -0.0049(6) C4 0.0196(7) 0.0260(8) 0.0198(7) 0.0051(6) 0.0021(6) -0.0069(6) C5 0.0264(8) 0.0179(7) 0.0149(7) 0.0010(6) 0.0005(6) -0.0009(6) C6 0.0211(7) 0.0223(7) 0.0130(6) -0.0021(6) 0.0044(5) -0.0024(5) C7 0.0206(7) 0.0198(7) 0.0157(7) -0.0001(6) 0.0054(5) -0.0006(5) 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' 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 C7 N1 H1 119.2(12) ? C7 N1 H2 118.0(11) ? H1 N1 H2 122.6(17) ? C2 C1 C6 116.59(13) y C2 C1 C7 122.90(13) ? C6 C1 C7 120.37(12) ? F2 C2 C3 117.15(13) ? F2 C2 C1 120.65(13) ? C3 C2 C1 122.18(14) ? F3 C3 C4 119.97(14) ? F3 C3 C2 120.36(14) ? C4 C3 C2 119.66(13) ? F4 C4 C3 120.35(14) ? F4 C4 C5 120.00(14) ? C3 C4 C5 119.65(13) ? F5 C5 C4 119.87(13) ? F5 C5 C6 120.19(13) ? C4 C5 C6 119.94(14) ? F6 C6 C5 117.49(13) ? F6 C6 C1 120.54(13) ? C5 C6 C1 121.97(13) ? O1 C7 N1 123.90(14) y O1 C7 C1 119.08(13) y N1 C7 C1 117.02(12) y 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 F2 C2 . 1.3459(17) ? F3 C3 . 1.3370(16) ? F4 C4 . 1.3363(17) ? F5 C5 . 1.3419(17) ? F6 C6 . 1.3410(16) ? O1 C7 . 1.2392(17) y N1 C7 . 1.3217(19) y N1 H1 . 0.88(2) ? N1 H2 . 0.89(2) ? C1 C2 . 1.393(2) ? C1 C6 . 1.393(2) ? C1 C7 . 1.513(2) y C2 C3 . 1.386(2) ? C3 C4 . 1.380(2) ? C4 C5 . 1.382(2) ? C5 C6 . 1.383(2) ? 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 H1 O1 4_575 0.88(2) 2.05(2) 2.8902(17) 158.3(17) N1 H2 O1 3_575 0.89(2) 2.03(2) 2.9137(17) 175.5(16) 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 C2 C1 C7 O1 -134.44(15) ? C2 C1 C7 N1 44.8(2) y C6 C1 C7 O1 41.2(2) y C6 C1 C7 N1 -139.53(14) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 62751 2 PubChem 69547