#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/53/2015389.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_2015389 loop_ _publ_author_name 'Garden, Simon J.' 'Pinto, Angelo C.' 'Wardell, James L.' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; Hydrogen-bonded chains of rings linked by iodo--carbonyl interactions in 5-iodoisatin and hydrogen-bonded sheets in 7-trifluoromethylisatin ; _journal_coeditor_code SK3019 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o321 _journal_page_last o323 _journal_paper_doi 10.1107/S0108270106014284 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C9 H4 F3 N O2' _chemical_formula_moiety 'C9 H4 F3 N O2' _chemical_formula_sum 'C9 H4 F3 N O2' _chemical_formula_weight 215.13 _chemical_name_common 7-trifluoromethylisatin _chemical_name_systematic ; 7-trifluoromethyl-1H-indole-2,3-dione ; _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 102.713(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.1704(2) _cell_length_b 15.5609(11) _cell_length_c 10.5780(7) _cell_measurement_reflns_used 1893 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.54 _cell_measurement_theta_min 3.95 _cell_volume 830.20(9) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT' _computing_data_collection 'COLLECT (Hooft, 1999)' _computing_data_reduction 'DENZO and COLLECT' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9.091 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker--Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Bruker--Nonius FR591 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9284 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 27.54 _diffrn_reflns_theta_min 3.95 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.166 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_correction_T_min 0.934 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.286 _refine_diff_density_min -0.262 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 1893 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0409 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.3729P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0950 _refine_ls_wR_factor_ref 0.1054 _reflns_number_gt 1412 _reflns_number_total 1893 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk3019.cif _cod_data_source_block II _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2015389 _cod_database_fobs_code 2015389 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_type_symbol _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 N N1 0.3672(3) 0.41319(9) 0.58953(14) 0.0247(3) Uani d . 1 C C2 0.5015(3) 0.37017(11) 0.51217(16) 0.0241(4) Uani d . 1 O O2 0.6305(3) 0.40066(8) 0.43947(12) 0.0297(3) Uani d . 1 C C3 0.4568(3) 0.27249(11) 0.53387(16) 0.0238(4) Uani d . 1 O O3 0.5537(3) 0.21499(8) 0.48362(13) 0.0314(3) Uani d . 1 C C3A 0.2815(3) 0.27031(11) 0.62630(16) 0.0231(4) Uani d . 1 C C4 0.1682(4) 0.20243(11) 0.67924(18) 0.0275(4) Uani d . 1 C C5 0.0043(4) 0.22067(12) 0.76393(18) 0.0297(4) Uani d . 1 C C6 -0.0380(3) 0.30540(12) 0.79553(17) 0.0267(4) Uani d . 1 C C7 0.0772(3) 0.37402(11) 0.74381(16) 0.0230(4) Uani d . 1 C C71 0.0352(4) 0.46486(12) 0.78114(18) 0.0293(4) Uani d . 1 F F71 -0.1323(3) 0.47130(8) 0.85986(13) 0.0521(4) Uani d . 1 F F72 0.2598(2) 0.50350(8) 0.83885(13) 0.0511(4) Uani d . 1 F F73 -0.0669(2) 0.51364(7) 0.67699(11) 0.0389(3) Uani d . 1 C C7A 0.2354(3) 0.35583(10) 0.65696(16) 0.0218(4) Uani d . 1 H H1 0.3632 0.4695 0.5965 0.046(6) Uiso calc R 1 H H4 0.2017 0.1447 0.6582 0.033 Uiso calc R 1 H H5 -0.0786 0.1752 0.8001 0.036 Uiso calc R 1 H H6 -0.1489 0.3169 0.8542 0.032 Uiso calc R 1 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 N1 0.0319(8) 0.0174(7) 0.0306(8) -0.0022(6) 0.0191(6) 0.0002(6) C2 0.0261(9) 0.0220(9) 0.0268(9) -0.0010(7) 0.0116(7) 0.0003(7) O2 0.0361(7) 0.0254(7) 0.0351(7) -0.0033(5) 0.0237(6) 0.0005(5) C3 0.0246(9) 0.0226(9) 0.0265(9) 0.0000(7) 0.0107(7) 0.0003(7) O3 0.0366(7) 0.0270(7) 0.0353(7) 0.0037(5) 0.0179(6) -0.0030(5) C3A 0.0254(9) 0.0207(9) 0.0257(9) 0.0003(6) 0.0110(7) 0.0018(7) C4 0.0323(10) 0.0190(9) 0.0338(9) 0.0011(7) 0.0135(7) 0.0026(7) C5 0.0316(10) 0.0268(9) 0.0338(10) -0.0032(7) 0.0142(8) 0.0081(8) C6 0.0263(9) 0.0300(10) 0.0277(9) 0.0012(7) 0.0143(7) 0.0045(7) C7 0.0249(9) 0.0223(9) 0.0249(8) 0.0020(6) 0.0119(7) 0.0007(7) C71 0.0331(10) 0.0285(10) 0.0316(10) 0.0005(7) 0.0185(8) -0.0013(8) F71 0.0757(9) 0.0365(7) 0.0624(8) 0.0061(6) 0.0549(7) -0.0026(6) F72 0.0464(8) 0.0383(7) 0.0654(9) -0.0029(6) 0.0050(6) -0.0205(6) F73 0.0528(7) 0.0229(6) 0.0437(7) 0.0070(5) 0.0165(5) 0.0037(5) C7A 0.0221(8) 0.0208(9) 0.0249(8) -0.0002(6) 0.0106(7) 0.0030(7) 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' F F 0.0171 0.0103 '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' 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 C2 N1 C7A 111.16(14) no C2 N1 H1 124.4 no C7A N1 H1 124.4 no O2 C2 N1 127.62(16) no O2 C2 C3 126.19(15) no N1 C2 C3 106.18(13) no O3 C3 C3A 130.72(16) no O3 C3 C2 124.65(15) no C3A C3 C2 104.63(13) no C4 C3A C7A 121.46(15) no C4 C3A C3 131.53(15) no C7A C3A C3 107.01(14) no C3A C4 C5 118.47(16) no C3A C4 H4 120.8 no C5 C4 H4 120.8 no C6 C5 C4 119.93(16) no C6 C5 H5 120.0 no C4 C5 H5 120.0 no C5 C6 C7 121.98(15) no C5 C6 H6 119.0 no C7 C6 H6 119.0 no C7A C7 C6 118.01(16) no C7A C7 C71 120.57(15) no C6 C7 C71 121.42(14) no F72 C71 F71 107.53(15) no F72 C71 F73 105.44(15) no F71 C71 F73 106.10(14) no F72 C71 C7 112.67(15) no F71 C71 C7 112.86(15) no F73 C71 C7 111.73(14) no C7 C7A C3A 120.12(15) no C7 C7A N1 128.88(15) no C3A C7A N1 111.00(14) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.360(2) no N1 C7A 1.408(2) no N1 H1 0.88 no C2 O2 1.219(2) no C2 C3 1.562(2) no C3 O3 1.205(2) no C3 C3A 1.473(2) no C3A C4 1.384(2) no C3A C7A 1.402(2) no C4 C5 1.391(2) no C4 H4 0.95 no C5 C6 1.389(3) no C5 H5 0.95 no C6 C7 1.392(2) no C6 H6 0.95 no C7 C7A 1.387(2) no C7 C71 1.496(2) no C71 F72 1.330(2) no C71 F71 1.3308(19) no C71 F73 1.346(2) no 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 _geom_hbond_publ_flag N1 H1 O2 3_666 0.88 2.06 2.913(2) 164 y C6 H6 O3 4_455 0.95 2.33 3.219(2) 156 y 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 C7A N1 C2 O2 178.32(17) no C7A N1 C2 C3 -1.30(19) no O2 C2 C3 O3 2.7(3) no N1 C2 C3 O3 -177.70(16) no O2 C2 C3 C3A -178.05(17) no N1 C2 C3 C3A 1.58(18) no O3 C3 C3A C4 -2.7(3) no C2 C3 C3A C4 178.08(19) no O3 C3 C3A C7A 177.95(18) no C2 C3 C3A C7A -1.27(18) no C7A C3A C4 C5 0.4(3) no C3 C3A C4 C5 -178.87(17) no C3A C4 C5 C6 -1.3(3) no C4 C5 C6 C7 0.7(3) no C5 C6 C7 C7A 0.9(3) no C5 C6 C7 C71 -178.51(17) no C7A C7 C71 F72 -61.3(2) no C6 C7 C71 F72 118.12(18) no C7A C7 C71 F71 176.71(16) no C6 C7 C71 F71 -3.9(2) no C7A C7 C71 F73 57.2(2) no C6 C7 C71 F73 -123.39(17) no C6 C7 C7A C3A -1.8(2) no C71 C7 C7A C3A 177.62(16) no C6 C7 C7A N1 178.26(17) no C71 C7 C7A N1 -2.3(3) no C4 C3A C7A C7 1.2(3) no C3 C3A C7A C7 -179.40(15) no C4 C3A C7A N1 -178.87(16) no C3 C3A C7A N1 0.56(19) no C2 N1 C7A C7 -179.52(17) no C2 N1 C7A C3A 0.5(2) no