data_2007306
_journal_name_full  'Acta Crystallographica'
_journal_year  1998
_journal_volume  C54
_journal_page_first  856
_journal_page_last  859
_publ_section_title
;
 2-Amino-5-nitrobenzophenone and
2-Methylamino-2'-fluoro-5-nitrobenzophenone
;
loop_
_publ_author_name
  ' Philip J. Cox'
  ' Abu T. Md. Anisuzzaman'
  ' R. Howard Pryce-Jones'
  ' Graham G. Skellern'
  ' Alastair J. Florence'
  ' Norman Shankland'
_chemical_formula_moiety  'C14 H11 F N2 O3'
_chemical_formula_sum  'C14 H11 F N2 O3'
_chemical_formula_weight  274.25
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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'
_cell_length_a  4.2150(17)
_cell_length_b  13.6020(18)
_cell_length_c  21.547(7)
_cell_angle_alpha  90.00
_cell_angle_beta  94.7480(11)
_cell_angle_gamma  90.00
_cell_volume  1231.1(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.480
_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  .1197(4)  .37583(12)  .02766(8)  .0400(5) Uani d . 1 . . F
  O1  .1869(5)  .09796(15)  -.00273(9)  .0380(6) Uani d . 1 . . O
  O2  .9377(5)  .35503(16)  .25413(10)  .0433(7) Uani d . 1 . . O
  O3  .9450(5)  .41232(17)  .16025(10)  .0447(7) Uani d . 1 . . O
  N1  .1046(5)  .03345(17)  .11140(11)  .0286(7) Uani d . 1 . . N
  H1  .0626  .0256  .0710  .026(3) Uiso calc R 1 . . H
  N2  .8582(6)  .3510(2)  .19769(13)  .0322(7) Uani d . 1 . . N
  C1  .3884(7)  .1822(2)  .08866(13)  .0225(8) Uani d . 1 . . C
  C2  .2802(7)  .1116(2)  .13109(13)  .0236(8) Uani d . 1 . . C
  C3  .3654(7)  .1256(2)  .19589(13)  .0281(8) Uani d . 1 . . C
  H3  .2916  .0802  .2249  .026(3) Uiso calc R 1 . . H
  C4  .5508(7)  .2031(2)  .21729(14)  .0289(8) Uani d . 1 . . C
  H4  .6073  .2107  .2606  .026(3) Uiso calc R 1 . . H
  C5  .6560(7)  .2706(2)  .17490(14)  .0231(8) Uani d . 1 . . C
  C6  .5761(7)  .2603(2)  .11215(14)  .0238(8) Uani d . 1 . . C
  H6  .6504  .3073  .0842  .026(3) Uiso calc R 1 . . H
  C7  .3119(7)  .1723(2)  .02075(14)  .0256(8) Uani d . 1 . . C
  C8  .3961(7)  .2531(2)  -.02285(13)  .0224(7) Uani d . 1 . . C
  C9  .2946(7)  .3492(2)  -.02019(13)  .0251(8) Uani d . 1 . . C
  C10  .3529(7)  .4192(2)  -.06339(13)  .0313(8) Uani d . 1 . . C
  H10  .2759  .4844  -.0596  .026(3) Uiso calc R 1 . . H
  C11  .5245(7)  .3936(2)  -.11234(14)  .0363(9) Uani d . 1 . . C
  H11  .5712  .4414  -.1424  .026(3) Uiso calc R 1 . . H
  C12  .6295(7)  .2974(3)  -.11775(14)  .0364(9) Uani d . 1 . . C
  H12  .7469  .2795  -.1518  .026(3) Uiso calc R 1 . . H
  C13  .5644(7)  .2279(2)  -.07405(13)  .0302(8) Uani d . 1 . . C
  H13  .6343  .1621  -.0787  .026(3) Uiso calc R 1 . . H
  C14  -.0218(7)  -.0399(2)  .15307(13)  .0325(9) Uani d . 1 . . C
  H14A  -.1426  -.0897  .1282  .070(6) Uiso calc R 1 . . H
  H14B  -.1619  -.0073  .1808  .070(6) Uiso calc R 1 . . H
  H14C  .1550  -.0714  .1779  .070(6) 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
  F1  .0455(12)  .0370(12)  .0389(11)  .0060(10)  .0108(10)  -.0005(10)
  O1  .0552(16)  .0294(14)  .0280(13)  -.0147(13)  -.0052(12)  -.0035(12)
  O2  .0525(16)  .0520(17)  .0231(13)  -.0076(13)  -.0101(12)  -.0111(13)
  O3  .0541(16)  .0413(16)  .0372(15)  -.0165(13)  -.0049(12)  .0034(13)
  N1  .0352(16)  .0299(17)  .0202(15)  -.0003(15)  -.0021(13)  .0049(14)
  N2  .0271(18)  .0363(19)  .0325(19)  .0036(15)  -.0020(15)  -.0069(16)
  C1  .0217(19)  .0230(19)  .0223(19)  .0037(16)  -.0006(15)  .0022(16)
  C2  .0220(19)  .022(2)  .027(2)  .0016(16)  .0002(15)  -.0055(16)
  C3  .031(2)  .031(2)  .0220(19)  .0026(18)  .0018(16)  .0006(17)
  C4  .034(2)  .037(2)  .0167(18)  .0032(18)  .0020(16)  -.0049(17)
  C5  .0206(19)  .0253(19)  .0227(19)  .0049(16)  -.0034(15)  -.0050(17)
  C6  .0266(19)  .0220(19)  .0225(19)  .0055(17)  -.0006(15)  .0004(16)
  C7  .025(2)  .024(2)  .027(2)  .0002(16)  -.0003(16)  -.0019(17)
  C8  .0230(19)  .024(2)  .0196(18)  -.0037(16)  -.0040(14)  -.0021(16)
  C9  .025(2)  .030(2)  .0198(18)  -.0008(17)  .0035(15)  -.0049(16)
  C10  .038(2)  .024(2)  .0303(19)  -.0010(17)  -.0045(17)  .0015(17)
  C11  .040(2)  .038(2)  .030(2)  -.0129(19)  .0009(17)  .0048(18)
  C12  .033(2)  .045(3)  .032(2)  -.0081(19)  .0077(17)  -.0039(19)
  C13  .034(2)  .029(2)  .027(2)  -.0028(17)  -.0018(17)  -.0030(17)
  C14  .034(2)  .026(2)  .037(2)  -.0014(17)  .0024(17)  .0065(17)
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 C9 . 1.365(3) Y
  O1 C7 . 1.230(3) Y
  O2 N2 . 1.236(3) Y
  O3 N2 . 1.236(3) Y
  N1 C2 . 1.343(3) Y
  N1 C14 . 1.471(3) N
  N2 C5 . 1.447(4) Y
  C1 C6 . 1.395(4) N
  C1 C2 . 1.427(4) N
  C1 C7 . 1.478(4) N
  C2 C3 . 1.425(4) N
  C3 C4 . 1.369(4) N
  C4 C5 . 1.393(4) N
  C5 C6 . 1.373(4) N
  C7 C8 . 1.507(4) N
  C8 C9 . 1.377(4) N
  C8 C13 . 1.403(3) N
  C9 C10 . 1.368(4) N
  C10 C11 . 1.372(3) N
  C11 C12 . 1.388(4) N
  C12 C13 . 1.378(4) N