data_2013985
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o318
_journal_page_last  o320
_publ_section_title
;
5-(2-Chlorophenyldiazenyl)salicylaldehyde and
4-(2-chlorophenyldiazenyl)-2-
{[tris(hydroxymethyl)methyl]aminomethylene}cyclohexa-3,5-dien-1(2H)-one
;
loop_
_publ_author_name
  "Albayrak, \,Ci\<gdem"
  "Odaba\;so\<glu, Mustafa"
  "B\"uy\"ukg\"ung\"or, Orhan"
  "L\"onnecke, Peter"
_chemical_formula_moiety  'C17 H18 Cl N3 O4'
_chemical_formula_sum  'C17 H18 Cl N3 O4'
_chemical_formula_iupac  'C17 H18 Cl N3 O4'
_chemical_formula_weight  363.79
_chemical_melting_point  '479-481'
_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  16.122(3)
_cell_length_b  8.3847(12)
_cell_length_c  13.359(2)
_cell_angle_alpha  90.00
_cell_angle_beta  110.689(3)
_cell_angle_gamma  90.00
_cell_volume  1689.4(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  213(2)
_exptl_crystal_density_diffrn  1.430
_diffrn_ambient_temperature  213(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 0.60359(4) 0.35489(7) 0.52771(5) 0.0584(2) Uani d . 1 . . Cl
  O1 0.10407(7) 0.35993(13) 0.06417(9) 0.0268(3) Uani d . 1 . . O
  O2 -0.12329(9) 0.32805(15) -0.06353(9) 0.0319(3) Uani d . 1 . . O
  O4 -0.13144(9) 0.27918(16) 0.23544(10) 0.0364(3) Uani d . 1 . . O
  O3 -0.05874(9) -0.11636(15) 0.08949(10) 0.0341(3) Uani d . 1 . . O
  N1 0.42847(9) 0.21133(18) 0.47415(11) 0.0314(3) Uani d . 1 . . N
  N2 0.34956(9) 0.16842(18) 0.45484(11) 0.0323(3) Uani d . 1 . . N
  N3 -0.01545(9) 0.20702(16) 0.12104(10) 0.0217(3) Uani d . 1 . . N
  C1 0.48879(11) 0.1572(2) 0.57426(13) 0.0303(4) Uani d . 1 . . C
  C2 0.57490(12) 0.2178(2) 0.60750(14) 0.0360(4) Uani d . 1 . . C
  C3 0.63803(14) 0.1710(3) 0.70347(16) 0.0450(5) Uani d . 1 . . C
  C4 0.61604(14) 0.0615(3) 0.76676(16) 0.0482(5) Uani d . 1 . . C
  C5 0.53168(15) -0.0016(3) 0.73474(16) 0.0466(5) Uani d . 1 . . C
  C6 0.46863(13) 0.0447(2) 0.63908(15) 0.0378(4) Uani d . 1 . . C
  C7 0.29029(11) 0.2201(2) 0.35382(13) 0.0278(4) Uani d . 1 . . C
  C8 0.20345(11) 0.1748(2) 0.32736(14) 0.0283(4) Uani d . 1 . . C
  C9 0.13867(11) 0.21684(19) 0.22878(13) 0.0244(3) Uani d . 1 . . C
  C10 0.16284(11) 0.31197(18) 0.15440(13) 0.0240(3) Uani d . 1 . . C
  C11 0.25369(12) 0.3535(2) 0.18322(14) 0.0319(4) Uani d . 1 . . C
  C12 0.31529(12) 0.3103(2) 0.27925(14) 0.0326(4) Uani d . 1 . . C
  C13 0.04935(11) 0.16657(19) 0.20657(13) 0.0248(4) Uani d . 1 . . C
  C14 -0.10832(10) 0.15382(18) 0.08636(12) 0.0215(3) Uani d . 1 . . C
  C15 -0.16372(12) 0.2836(2) 0.01114(13) 0.0268(4) Uani d . 1 . . C
  C17 -0.13889(12) 0.1321(2) 0.18129(13) 0.0255(4) Uani d . 1 . . C
  C16 -0.11721(12) -0.00217(19) 0.02397(13) 0.0274(4) Uani d . 1 . . C
  H22 -0.1163(15) 0.430(3) -0.0611(18) 0.055(7) Uiso d . 1 . . H
  H44 -0.1297(17) 0.259(3) 0.292(2) 0.060(8) Uiso d . 1 . . H
  H33 -0.0689(15) -0.202(3) 0.0509(18) 0.052(7) Uiso d . 1 . . H
  H1 -0.0041(14) 0.272(3) 0.0764(16) 0.047(6) Uiso d . 1 . . H
  H3 0.6928(17) 0.213(3) 0.7243(18) 0.054(6) Uiso d . 1 . . H
  H4 0.6577(15) 0.029(3) 0.8299(18) 0.053(6) Uiso d . 1 . . H
  H5 0.5206(15) -0.083(3) 0.7765(18) 0.052(6) Uiso d . 1 . . H
  H6 0.4108(15) -0.002(2) 0.6123(16) 0.049(6) Uiso d . 1 . . H
  H8 0.1903(14) 0.111(2) 0.3787(17) 0.043(6) Uiso d . 1 . . H
  H11 0.2715(13) 0.421(2) 0.1317(15) 0.037(5) Uiso d . 1 . . H
  H12 0.3755(14) 0.343(2) 0.2979(15) 0.037(5) Uiso d . 1 . . H
  H13 0.0387(12) 0.099(2) 0.2605(15) 0.033(5) Uiso d . 1 . . H
  H15A -0.1704(11) 0.378(2) 0.0528(14) 0.027(5) Uiso d . 1 . . H
  H15B -0.2240(14) 0.242(2) -0.0289(15) 0.037(5) Uiso d . 1 . . H
  H17A -0.2007(13) 0.097(2) 0.1530(14) 0.028(4) Uiso d . 1 . . H
  H17B -0.1059(12) 0.051(2) 0.2260(14) 0.024(4) Uiso d . 1 . . H
  H16A -0.1818(13) -0.037(2) 0.0041(14) 0.033(5) Uiso d . 1 . . H
  H16B -0.1029(12) 0.018(2) -0.0409(15) 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
  Cl1 0.0344(3) 0.0714(4) 0.0619(4) -0.0117(3) 0.0077(2) 0.0179(3)
  O1 0.0286(6) 0.0264(6) 0.0249(6) -0.0011(5) 0.0087(5) 0.0033(4)
  O2 0.0483(8) 0.0267(7) 0.0230(6) 0.0023(6) 0.0154(5) 0.0044(5)
  O4 0.0523(9) 0.0369(7) 0.0241(7) 0.0017(6) 0.0187(6) -0.0041(5)
  O3 0.0429(8) 0.0259(7) 0.0312(7) 0.0060(5) 0.0100(6) 0.0003(5)
  N1 0.0246(8) 0.0366(8) 0.0305(8) 0.0021(6) 0.0063(6) -0.0017(6)
  N2 0.0242(8) 0.0396(9) 0.0313(8) 0.0023(6) 0.0075(6) 0.0012(6)
  N3 0.0243(7) 0.0231(7) 0.0194(7) -0.0014(5) 0.0097(6) 0.0007(5)
  C1 0.0246(9) 0.0380(10) 0.0281(9) 0.0048(7) 0.0088(7) -0.0054(7)
  C2 0.0288(9) 0.0443(11) 0.0334(10) 0.0028(8) 0.0092(8) -0.0015(8)
  C3 0.0278(10) 0.0608(14) 0.0387(11) 0.0012(10) 0.0024(9) -0.0060(9)
  C4 0.0408(12) 0.0668(15) 0.0289(10) 0.0147(11) 0.0024(9) 0.0043(10)
  C5 0.0459(12) 0.0597(14) 0.0346(10) 0.0090(10) 0.0148(9) 0.0105(9)
  C6 0.0291(10) 0.0495(12) 0.0353(10) 0.0032(9) 0.0120(8) 0.0023(8)
  C7 0.0247(8) 0.0286(9) 0.0285(8) 0.0025(7) 0.0072(7) 0.0010(7)
  C8 0.0277(9) 0.0293(9) 0.0273(9) -0.0007(7) 0.0088(7) 0.0043(7)
  C9 0.0243(8) 0.0235(8) 0.0256(8) -0.0006(6) 0.0092(7) -0.0014(6)
  C10 0.0269(8) 0.0205(8) 0.0244(8) 0.0009(6) 0.0088(7) -0.0021(6)
  C11 0.0289(9) 0.0357(10) 0.0337(9) -0.0032(7) 0.0141(8) 0.0043(8)
  C12 0.0234(9) 0.0367(10) 0.0373(10) -0.0020(7) 0.0104(8) 0.0014(8)
  C13 0.0270(9) 0.0250(8) 0.0234(8) -0.0015(7) 0.0102(7) 0.0006(6)
  C14 0.0217(8) 0.0240(8) 0.0185(7) -0.0021(6) 0.0067(6) -0.0008(6)
  C15 0.0295(9) 0.0278(9) 0.0227(8) 0.0025(7) 0.0087(7) 0.0023(7)
  C17 0.0256(9) 0.0300(9) 0.0227(8) -0.0017(7) 0.0109(7) 0.0006(7)
  C16 0.0308(9) 0.0260(9) 0.0234(8) -0.0008(7) 0.0071(7) -0.0023(6)
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 C2 . 1.737(2) ?
  O1 C10 . 1.306(2) yes
  O2 C15 . 1.421(2) ?
  O2 H22 . 0.86(3) ?
  O4 C17 . 1.413(2) ?
  O4 H44 . 0.77(3) ?
  O3 C16 . 1.410(2) ?
  O3 H33 . 0.86(2) ?
  N1 N2 . 1.258(2) yes
  N1 C1 . 1.422(2) yes
  N2 C7 . 1.418(2) yes
  N3 C13 . 1.292(2) yes
  N3 C14 . 1.471(2) ?
  N3 H1 . 0.87(2) ?
  C1 C6 . 1.394(3) ?
  C1 C2 . 1.396(2) ?
  C2 C3 . 1.383(3) ?
  C3 C4 . 1.376(3) ?
  C3 H3 . 0.90(2) ?
  C4 C5 . 1.379(3) ?
  C4 H4 . 0.92(2) ?
  C5 C6 . 1.378(3) ?
  C5 H5 . 0.93(2) ?
  C6 H6 . 0.96(2) ?
  C7 C8 . 1.371(2) yes
  C7 C12 . 1.418(2) ?
  C8 C9 . 1.406(2) ?
  C8 H8 . 0.95(2) ?
  C9 C13 . 1.427(2) yes
  C9 C10 . 1.431(2) yes
  C10 C11 . 1.420(2) ?
  C11 C12 . 1.365(2) yes
  C11 H11 . 1.01(2) ?
  C12 H12 . 0.95(2) ?
  C13 H13 . 0.98(2) ?
  C14 C17 . 1.525(2) ?
  C14 C16 . 1.530(2) ?
  C14 C15 . 1.535(2) ?
  C15 H15A . 0.995(18) ?
  C15 H15B . 0.99(2) ?
  C17 H17A . 0.98(2) ?
  C17 H17B . 0.94(2) ?
  C16 H16A . 1.02(2) ?
  C16 H16B . 0.99(2) ?