data_2013772 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2004 _journal_volume 60 _journal_page_first o219 _journal_page_last o222 _publ_section_title ; An analysis of C-H...O and C-H...\p interactions in three substituted 4-ketotetrahydroindoles ; loop_ _publ_author_name 'Choudhury, A. R' 'Nagarajan, K.' 'Guru Row, T. N.' _chemical_formula_moiety 'C22 H19 Cl F N O' _chemical_formula_sum 'C22 H19 Cl F N O' _chemical_formula_iupac 'C22 H19 Cl F N O' _chemical_formula_weight 367.83 _chemical_melting_point 507 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 9.246(3) _cell_length_b 10.228(4) _cell_length_c 11.177(4) _cell_angle_alpha 80.529(6) _cell_angle_beta 86.335(7) _cell_angle_gamma 65.120(6) _cell_volume 945.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.292 _diffrn_ambient_temperature 293(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 0.66030(9) 0.27487(8) 0.99603(6) 0.0893(3) Uani d . 1 . . Cl N1 0.74427(17) 0.54652(15) 0.39864(14) 0.0445(4) Uani d . 1 . . N O1 0.5159(3) 1.04382(16) 0.30251(16) 0.0989(7) Uani d . 1 . . O F1 1.1009(2) -0.02663(15) 0.34244(18) 0.1180(6) Uani d . 1 . . F C1 0.6736(2) 0.60481(19) 0.50405(17) 0.0449(4) Uani d . 1 . . C C2 0.6048(2) 0.7529(2) 0.47288(19) 0.0505(5) Uani d . 1 . . C C3 0.5853(3) 0.9258(2) 0.2686(2) 0.0588(5) Uani d . 1 . . C C4 0.6250(3) 0.9138(2) 0.1373(2) 0.0600(6) Uani d . 1 . . C C5 0.7828(3) 0.7863(2) 0.1146(2) 0.0594(5) Uani d . 1 . . C C6 0.7775(3) 0.6433(2) 0.1792(2) 0.0572(5) Uani d . 1 . . C C7 0.7189(2) 0.65797(19) 0.30515(17) 0.0466(4) Uani d . 1 . . C C8 0.6317(2) 0.78683(19) 0.34852(18) 0.0487(5) Uani d . 1 . . C C9 0.8369(2) 0.39556(18) 0.38695(17) 0.0451(4) Uani d . 1 . . C C10 0.9871(3) 0.3220(2) 0.4367(2) 0.0607(6) Uani d . 1 . . C C11 1.0767(3) 0.1786(2) 0.4214(3) 0.0760(7) Uani d . 1 . . C C12 1.0124(3) 0.1143(2) 0.3575(2) 0.0734(7) Uani d . 1 . . C C13 0.8633(3) 0.1833(3) 0.3088(2) 0.0772(7) Uani d . 1 . . C C14 0.7741(3) 0.3273(2) 0.3234(2) 0.0637(6) Uani d . 1 . . C C15 0.6749(2) 0.51810(19) 0.62245(17) 0.0457(4) Uani d . 1 . . C C16 0.6757(3) 0.5763(2) 0.72673(19) 0.0551(5) Uani d . 1 . . C C17 0.6686(3) 0.5037(2) 0.8405(2) 0.0620(6) Uani d . 1 . . C C18 0.6626(2) 0.3697(2) 0.85213(19) 0.0570(5) Uani d . 1 . . C C19 0.6614(2) 0.3093(2) 0.7518(2) 0.0562(5) Uani d . 1 . . C C20 0.6669(2) 0.3830(2) 0.6379(2) 0.0508(5) Uani d . 1 . . C C21 0.8021(5) 0.7823(4) -0.0217(3) 0.0885(9) Uani d . 1 . . C C22 0.9196(4) 0.8080(4) 0.1648(4) 0.0913(9) Uani d . 1 . . C H2 0.547(2) 0.817(2) 0.5230(17) 0.049(5) Uiso d . 1 . . H H4A 0.625(2) 1.005(2) 0.0972(19) 0.063(6) Uiso d . 1 . . H H4B 0.539(3) 0.900(2) 0.1011(19) 0.068(6) Uiso d . 1 . . H H6A 0.880(3) 0.563(2) 0.1784(18) 0.061(6) Uiso d . 1 . . H H6B 0.705(2) 0.619(2) 0.1332(18) 0.057(6) Uiso d . 1 . . H H10 1.029(3) 0.369(2) 0.483(2) 0.072(7) Uiso d . 1 . . H H11 1.181(3) 0.129(3) 0.458(2) 0.093(8) Uiso d . 1 . . H H13 0.823(3) 0.136(3) 0.265(2) 0.087(8) Uiso d . 1 . . H H14 0.672(3) 0.380(3) 0.289(2) 0.083(8) Uiso d . 1 . . H H16 0.683(2) 0.666(2) 0.7170(18) 0.058(6) Uiso d . 1 . . H H17 0.669(3) 0.548(2) 0.909(2) 0.070(7) Uiso d . 1 . . H H19 0.659(2) 0.217(2) 0.7612(18) 0.060(6) Uiso d . 1 . . H H20 0.663(2) 0.341(2) 0.5701(19) 0.056(6) Uiso d . 1 . . H H21A 0.813(3) 0.870(3) -0.066(3) 0.105(9) Uiso d . 1 . . H H21B 0.711(4) 0.768(3) -0.060(3) 0.122(12) Uiso d . 1 . . H H21C 0.897(3) 0.703(3) -0.033(2) 0.082(8) Uiso d . 1 . . H H22A 1.010(4) 0.731(4) 0.149(3) 0.115(11) Uiso d . 1 . . H H22B 0.910(4) 0.811(3) 0.261(3) 0.121(11) Uiso d . 1 . . H H22C 0.926(3) 0.894(3) 0.123(3) 0.110(10) 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 Cl1 0.1093(6) 0.0859(5) 0.0681(4) -0.0433(4) 0.0167(4) 0.0020(3) N1 0.0443(9) 0.0342(8) 0.0510(9) -0.0102(6) -0.0023(7) -0.0121(7) O1 0.1506(18) 0.0356(9) 0.0811(12) -0.0081(10) -0.0041(11) -0.0136(8) F1 0.1249(14) 0.0436(8) 0.1618(17) -0.0023(8) 0.0004(12) -0.0426(9) C1 0.0418(10) 0.0387(10) 0.0535(11) -0.0126(8) -0.0030(8) -0.0151(8) C2 0.0500(11) 0.0385(10) 0.0581(13) -0.0091(9) -0.0026(9) -0.0189(9) C3 0.0648(13) 0.0404(11) 0.0633(14) -0.0118(10) -0.0105(10) -0.0106(10) C4 0.0698(15) 0.0411(11) 0.0642(14) -0.0197(10) -0.0120(11) 0.0001(10) C5 0.0628(13) 0.0518(12) 0.0597(13) -0.0213(10) 0.0017(10) -0.0061(10) C6 0.0633(14) 0.0435(11) 0.0578(13) -0.0140(10) 0.0020(11) -0.0125(10) C7 0.0457(10) 0.0376(10) 0.0533(11) -0.0126(8) -0.0071(9) -0.0088(8) C8 0.0497(11) 0.0372(10) 0.0544(12) -0.0112(8) -0.0080(9) -0.0106(8) C9 0.0470(11) 0.0340(9) 0.0521(11) -0.0131(8) 0.0021(8) -0.0117(8) C10 0.0505(12) 0.0414(11) 0.0883(16) -0.0140(9) -0.0091(11) -0.0161(11) C11 0.0538(14) 0.0440(12) 0.116(2) -0.0049(11) -0.0105(14) -0.0133(13) C12 0.0820(17) 0.0346(11) 0.0926(18) -0.0094(11) 0.0063(14) -0.0240(11) C13 0.097(2) 0.0520(13) 0.0861(18) -0.0246(14) -0.0119(15) -0.0310(13) C14 0.0649(14) 0.0492(12) 0.0741(15) -0.0148(11) -0.0128(12) -0.0218(11) C15 0.0384(10) 0.0385(10) 0.0564(12) -0.0101(8) -0.0006(8) -0.0127(9) C16 0.0665(13) 0.0401(11) 0.0595(13) -0.0209(10) 0.0032(10) -0.0142(10) C17 0.0736(15) 0.0586(13) 0.0546(13) -0.0254(11) 0.0065(11) -0.0187(11) C18 0.0514(12) 0.0539(12) 0.0599(13) -0.0180(9) 0.0083(10) -0.0069(10) C19 0.0509(12) 0.0448(11) 0.0736(15) -0.0213(9) 0.0075(10) -0.0099(11) C20 0.0483(11) 0.0454(11) 0.0609(13) -0.0188(9) 0.0031(9) -0.0164(10) C21 0.113(3) 0.0669(18) 0.0729(18) -0.0294(19) 0.0206(18) -0.0073(14) C22 0.0693(19) 0.086(2) 0.123(3) -0.0384(17) 0.0025(18) -0.010(2) 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 Cl1 C18 . 1.740(2) ? N1 C7 . 1.364(2) ? N1 C1 . 1.405(2) ? N1 C9 . 1.440(2) ? O1 C3 . 1.217(2) ? F1 C12 . 1.358(2) ? C1 C2 . 1.365(3) ? C1 C15 . 1.464(3) ? C2 C8 . 1.409(3) ? C2 H2 . 0.91(2) ? C3 C8 . 1.456(3) ? C3 C4 . 1.502(3) ? C4 C5 . 1.534(3) ? C4 H4A . 0.96(2) ? C4 H4B . 0.98(2) ? C5 C22 . 1.527(4) ? C5 C21 . 1.528(4) ? C5 C6 . 1.540(3) ? C6 C7 . 1.483(3) ? C6 H6A . 0.96(2) ? C6 H6B . 1.00(2) ? C7 C8 . 1.374(2) ? C9 C10 . 1.373(3) ? C9 C14 . 1.373(3) ? C10 C11 . 1.381(3) ? C10 H10 . 0.96(2) ? C11 C12 . 1.355(4) ? C11 H11 . 0.96(3) ? C12 C13 . 1.358(4) ? C13 C14 . 1.384(3) ? C13 H13 . 0.93(3) ? C14 H14 . 0.94(2) ? C15 C16 . 1.395(3) ? C15 C20 . 1.397(3) ? C16 C17 . 1.375(3) ? C16 H16 . 0.94(2) ? C17 C18 . 1.379(3) ? C17 H17 . 0.95(2) ? C18 C19 . 1.370(3) ? C19 C20 . 1.378(3) ? C19 H19 . 0.94(2) ? C20 H20 . 0.94(2) ? C21 H21A . 0.99(3) ? C21 H21B . 1.04(3) ? C21 H21C . 0.93(3) ? C22 H22A . 0.91(3) ? C22 H22B . 1.08(3) ? C22 H22C . 0.95(3) ?