data_2013026
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o645
_journal_page_last  o648
_publ_section_title
;
Structural motifs in acetoacetanilides: the effect of a fluorine substituent
;
loop_
_publ_author_name
  'Chisholm, Greig'
  'Kennedy, Alan R.'
  'Beaton, Laura'
  'Brook, Eve'
_chemical_formula_moiety  'C10 H10 F N O2'
_chemical_formula_sum  'C10 H10 F N O2'
_chemical_formula_weight  195.19
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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'
_cell_length_a  4.98110(10)
_cell_length_b  20.7383(4)
_cell_length_c  18.4869(5)
_cell_angle_alpha  90
_cell_angle_beta  93.0210(10)
_cell_angle_gamma  90
_cell_volume  1907.03(7)
_cell_formula_units_Z  8
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.360
_diffrn_ambient_temperature  150(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
  F1 0.1874(2) -0.01606(5) 0.71536(6) 0.0515(3) Uani d . 1 . . F
  F2 1.0148(2) 0.46448(6) 0.60064(6) 0.0530(3) Uani d . 1 . . F
  O1 0.9201(2) 0.31809(6) 0.81717(8) 0.0461(4) Uani d . 1 . . O
  O2 1.0559(2) 0.17888(6) 0.86595(6) 0.0364(3) Uani d . 1 . . O
  O3 0.2814(3) 0.13101(8) 0.49571(9) 0.0657(5) Uani d . 1 . . O
  O4 0.1370(2) 0.23385(6) 0.61212(6) 0.0350(3) Uani d . 1 . . O
  N1 0.9707(3) 0.17207(7) 0.74406(8) 0.0280(3) Uani d . 1 . . N
  N2 0.2276(3) 0.29041(7) 0.51023(8) 0.0286(3) Uani d . 1 . . N
  C1 1.3117(3) 0.37529(9) 0.78825(11) 0.0398(5) Uani d . 1 . . C
  H1A 1.3244 0.3822 0.7361 0.060 Uiso calc R 1 . . H
  H1B 1.4925 0.3704 0.8111 0.060 Uiso calc R 1 . . H
  H1C 1.2227 0.4124 0.8095 0.060 Uiso calc R 1 . . H
  C2 1.1525(3) 0.31581(8) 0.80048(9) 0.0286(4) Uani d . 1 . . C
  C3 1.2890(3) 0.25125(8) 0.79085(9) 0.0283(4) Uani d . 1 . . C
  H3A 1.3519 0.2480 0.7411 0.034 Uiso calc R 1 . . H
  H3B 1.4477 0.2479 0.8252 0.034 Uiso calc R 1 . . H
  C4 1.0979(3) 0.19680(8) 0.80404(9) 0.0270(4) Uani d . 1 . . C
  C5 0.7702(3) 0.12322(8) 0.74025(8) 0.0256(4) Uani d . 1 . . C
  C6 0.7142(4) 0.08381(9) 0.79735(9) 0.0368(4) Uani d . 1 . . C
  H6 0.8108 0.0888 0.8427 0.044 Uiso calc R 1 . . H
  C7 0.5166(4) 0.03679(9) 0.78881(10) 0.0407(5) Uani d . 1 . . C
  H7 0.4771 0.0094 0.8280 0.049 Uiso calc R 1 . . H
  C8 0.3803(3) 0.03054(9) 0.72346(10) 0.0345(4) Uani d . 1 . . C
  C9 0.4310(4) 0.06848(10) 0.66580(10) 0.0430(5) Uani d . 1 . . C
  H9 0.3345 0.0627 0.6206 0.052 Uiso calc R 1 . . H
  C10 0.6262(3) 0.11563(9) 0.67451(9) 0.0384(5) Uani d . 1 . . C
  H10 0.6621 0.1431 0.6351 0.046 Uiso calc R 1 . . H
  C11 -0.1344(4) 0.08412(9) 0.45956(12) 0.0467(5) Uani d . 1 . . C
  H11A -0.0231 0.0489 0.4424 0.070 Uiso calc R 1 . . H
  H11B -0.2555 0.0993 0.4197 0.070 Uiso calc R 1 . . H
  H11C -0.2405 0.0686 0.4992 0.070 Uiso calc R 1 . . H
  C12 0.0416(3) 0.13803(9) 0.48593(9) 0.0351(4) Uani d . 1 . . C
  C13 -0.0893(3) 0.20255(8) 0.50039(9) 0.0298(4) Uani d . 1 . . C
  H13A -0.1350 0.2246 0.4539 0.036 Uiso calc R 1 . . H
  H13B -0.2577 0.1956 0.5254 0.036 Uiso calc R 1 . . H
  C14 0.0998(3) 0.24434(8) 0.54685(9) 0.0272(4) Uani d . 1 . . C
  C15 0.4270(3) 0.33405(8) 0.53680(8) 0.0270(4) Uani d . 1 . . C
  C16 0.5582(3) 0.32950(9) 0.60445(9) 0.0360(4) Uani d . 1 . . C
  H16 0.5132 0.2958 0.6365 0.043 Uiso calc R 1 . . H
  C17 0.7553(3) 0.37394(9) 0.62576(10) 0.0391(5) Uani d . 1 . . C
  H17 0.8437 0.3713 0.6725 0.047 Uiso calc R 1 . . H
  C18 0.8198(3) 0.42101(9) 0.57919(10) 0.0359(4) Uani d . 1 . . C
  C19 0.6977(4) 0.42670(10) 0.51170(10) 0.0468(5) Uani d . 1 . . C
  H19 0.7480 0.4600 0.4798 0.056 Uiso calc R 1 . . H
  C20 0.5000(4) 0.38311(9) 0.49074(10) 0.0424(5) Uani d . 1 . . C
  H20 0.4122 0.3867 0.4440 0.051 Uiso calc R 1 . . H
  H1N 1.012(3) 0.1881(9) 0.7014(10) 0.034(5) Uiso d . 1 . . H
  H2N 0.178(3) 0.2956(9) 0.4644(11) 0.036(5) 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
  F1 0.0435(6) 0.0401(7) 0.0708(8) -0.0167(5) 0.0005(5) -0.0092(6)
  F2 0.0561(7) 0.0519(8) 0.0511(7) -0.0256(6) 0.0039(5) -0.0096(6)
  O1 0.0258(7) 0.0412(8) 0.0721(10) 0.0028(6) 0.0112(6) 0.0058(7)
  O2 0.0486(7) 0.0381(8) 0.0221(6) -0.0084(6) -0.0017(5) 0.0008(5)
  O3 0.0300(8) 0.0649(11) 0.1011(13) 0.0088(7) -0.0071(7) -0.0276(9)
  O4 0.0387(7) 0.0434(8) 0.0227(7) -0.0092(6) -0.0006(5) 0.0078(5)
  N1 0.0331(8) 0.0309(9) 0.0203(7) -0.0050(6) 0.0036(6) 0.0005(6)
  N2 0.0334(8) 0.0331(9) 0.0192(8) -0.0037(6) -0.0018(6) 0.0035(6)
  C1 0.0304(10) 0.0319(11) 0.0571(13) 0.0004(8) 0.0009(8) -0.0009(9)
  C2 0.0253(9) 0.0310(11) 0.0290(9) 0.0000(7) -0.0042(6) 0.0008(7)
  C3 0.0261(8) 0.0302(10) 0.0285(9) -0.0014(7) 0.0001(7) -0.0022(7)
  C4 0.0285(8) 0.0276(10) 0.0249(9) 0.0021(7) 0.0010(6) -0.0025(7)
  C5 0.0280(8) 0.0232(10) 0.0259(9) 0.0006(7) 0.0025(6) -0.0025(7)
  C6 0.0445(10) 0.0370(11) 0.0286(10) -0.0098(9) -0.0025(7) 0.0018(8)
  C7 0.0502(11) 0.0355(12) 0.0370(11) -0.0127(9) 0.0073(8) 0.0026(9)
  C8 0.0286(9) 0.0252(10) 0.0497(12) -0.0045(7) 0.0035(8) -0.0082(8)
  C9 0.0453(11) 0.0437(13) 0.0385(11) -0.0102(9) -0.0114(8) -0.0039(9)
  C10 0.0468(11) 0.0404(12) 0.0274(10) -0.0095(9) -0.0031(8) 0.0049(8)
  C11 0.0444(11) 0.0359(12) 0.0593(13) -0.0001(9) -0.0001(9) -0.0036(10)
  C12 0.0335(10) 0.0410(12) 0.0306(10) 0.0010(8) 0.0014(7) -0.0009(8)
  C13 0.0273(8) 0.0358(11) 0.0260(9) -0.0013(8) -0.0007(6) 0.0024(8)
  C14 0.0260(8) 0.0310(10) 0.0245(9) 0.0023(7) 0.0020(6) 0.0027(7)
  C15 0.0277(9) 0.0284(10) 0.0251(9) 0.0024(7) 0.0043(7) -0.0008(7)
  C16 0.0390(10) 0.0403(12) 0.0284(10) -0.0069(9) -0.0021(7) 0.0075(8)
  C17 0.0395(10) 0.0471(13) 0.0302(10) -0.0078(9) -0.0026(8) -0.0001(9)
  C18 0.0354(10) 0.0340(11) 0.0387(11) -0.0086(8) 0.0054(8) -0.0100(9)
  C19 0.0624(13) 0.0410(13) 0.0372(11) -0.0179(10) 0.0044(9) 0.0079(9)
  C20 0.0540(12) 0.0438(13) 0.0287(10) -0.0139(10) -0.0033(8) 0.0084(9)
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
  F1 C8 . 1.3655(19) y
  F2 C18 . 1.3685(19) y
  O1 C2 . 1.2146(19) y
  O2 C4 . 1.2317(19) y
  O3 C12 . 1.208(2) y
  O4 C14 . 1.2304(18) y
  N1 C4 . 1.349(2) y
  N1 C5 . 1.422(2) y
  N1 H1N . 0.889(18) ?
  N2 C14 . 1.350(2) y
  N2 C15 . 1.413(2) y
  N2 H2N . 0.876(19) ?
  C1 C2 . 1.490(2) ?
  C1 H1A . 0.9800 ?
  C1 H1B . 0.9800 ?
  C1 H1C . 0.9800 ?
  C2 C3 . 1.517(2) ?
  C3 C4 . 1.505(2) ?
  C3 H3A . 0.9900 ?
  C3 H3B . 0.9900 ?
  C5 C6 . 1.375(2) ?
  C5 C10 . 1.387(2) ?
  C6 C7 . 1.389(2) ?
  C6 H6 . 0.9500 ?
  C7 C8 . 1.360(3) ?
  C7 H7 . 0.9500 ?
  C8 C9 . 1.359(3) ?
  C9 C10 . 1.382(2) ?
  C9 H9 . 0.9500 ?
  C10 H10 . 0.9500 ?
  C11 C12 . 1.487(3) ?
  C11 H11A . 0.9800 ?
  C11 H11B . 0.9800 ?
  C11 H11C . 0.9800 ?
  C12 C13 . 1.518(3) ?
  C13 C14 . 1.513(2) ?
  C13 H13A . 0.9900 ?
  C13 H13B . 0.9900 ?
  C15 C16 . 1.383(2) ?
  C15 C20 . 1.387(2) ?
  C16 C17 . 1.388(2) ?
  C16 H16 . 0.9500 ?
  C17 C18 . 1.351(3) ?
  C17 H17 . 0.9500 ?
  C18 C19 . 1.364(3) ?
  C19 C20 . 1.377(3) ?
  C19 H19 . 0.9500 ?
  C20 H20 . 0.9500 ?