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The title compound, 2-{(E)-3-[(E)-4-chloro­phenyl­imino]-4-hydroxy­phenyl­diazenyl}benzoic acid hemihydrate, C20H14ClN3O3·0.5H2O, forms sheets, parallel to the (100) plane, that are linked by weak aromatic C—H...O interactions. These sheets are in turn linked by strong hydrogen bonds to interstitial water mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007373/gh6012sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007373/gh6012Isup2.hkl
Contains datablock I

CCDC reference: 270324

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.076
  • wR factor = 0.216
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT731_ALERT_1_B Bond Calc 0.85(7), Rep 0.852(10) ...... 7.00 su-Rat O1W -H1W1 1.555 1.555 PLAT735_ALERT_1_B D-H Calc 0.85(7), Rep 0.852(10) ...... 7.00 su-Rat O1W -H1# 1.555 1.555
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1 PLAT736_ALERT_1_C H...A Calc 2.05(7), Rep 2.05(3) ...... 2.33 su-Rat H1# -O1 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL97 (Sheldrick, 1997); program(s) used to solve structure: SHELXTL97; program(s) used to refine structure: SHELXTL97; molecular graphics: SHELXTL97; software used to prepare material for publication: SHELXTL97.

2-{(E)-3-[(E)-4-chlorophenylimino]-4-hydroxyphenyldiazenyl}benzoic acid hemihydrate top
Crystal data top
C20H14ClN3O3·0.5H2ODx = 1.422 Mg m3
Mr = 388.80Melting point = 498–499 K
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
a = 13.2451 (19) ÅCell parameters from 49 reflections
b = 21.668 (4) Åθ = 5.4–27.8°
c = 12.664 (2) ŵ = 2.12 mm1
β = 91.69 (2)°T = 293 K
V = 3632.8 (10) Å3Prism, red
Z = 80.50 × 0.35 × 0.28 mm
F(000) = 1608
Data collection top
Bruker P4
diffractometer
1707 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 69.1°, θmin = 3.9°
2θ/ω scansh = 016
Absorption correction: part of the refinement model (ΔF)
(SHELX97; Sheldrick, 1998)
k = 026
Tmin = 0.415, Tmax = 0.552l = 1515
3534 measured reflections3 standard reflections every 97 reflections
3382 independent reflections intensity decay: 0.3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0577P)2 + 7.4356P]
where P = (Fo2 + 2Fc2)/3
3382 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.25 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl0.40742 (17)0.07579 (9)1.12841 (12)0.1232 (8)
O10.4080 (4)0.37481 (19)0.0762 (3)0.1179 (17)
O20.3795 (3)0.30536 (16)0.0423 (3)0.0853 (11)
H2O0.37670.30290.10670.102*
O30.3182 (4)0.09637 (16)0.4948 (3)0.0943 (13)
H3O0.32650.09680.55920.113*
O1W0.50000.3132 (3)0.25000.117 (2)
H1W10.480 (7)0.337 (3)0.202 (5)0.176*
N10.3712 (3)0.33810 (18)0.2377 (3)0.0639 (10)
N20.3807 (3)0.33039 (18)0.3368 (3)0.0671 (10)
N30.3639 (3)0.13951 (18)0.6768 (3)0.0648 (10)
C10.3930 (4)0.3631 (2)0.0152 (4)0.0778 (15)
C20.3843 (4)0.4122 (2)0.0964 (4)0.0653 (12)
C30.3863 (4)0.4728 (2)0.0619 (4)0.0793 (15)
H3A0.39320.48080.00960.095*
C40.3782 (4)0.5214 (2)0.1313 (4)0.0815 (16)
H4A0.37930.56170.10640.098*
C50.3685 (4)0.5101 (2)0.2382 (4)0.0796 (15)
H5A0.36290.54280.28510.096*
C60.3671 (4)0.4502 (2)0.2751 (4)0.0689 (13)
H6A0.36030.44260.34680.083*
C70.3758 (3)0.4010 (2)0.2049 (4)0.0621 (12)
C80.3666 (4)0.2690 (2)0.3703 (4)0.0647 (12)
C90.3358 (4)0.2192 (2)0.3061 (4)0.0796 (15)
H9A0.32650.22490.23370.096*
C100.3195 (5)0.1626 (3)0.3493 (4)0.0884 (17)
H10A0.29820.13010.30600.106*
C110.3340 (4)0.1527 (2)0.4566 (4)0.0736 (14)
C120.3668 (3)0.2014 (2)0.5231 (4)0.0627 (12)
C130.3816 (3)0.2593 (2)0.4780 (4)0.0635 (12)
H13A0.40200.29210.52100.076*
C140.3806 (4)0.1925 (2)0.6351 (4)0.0687 (13)
H14A0.40180.22530.67770.082*
C150.3749 (3)0.1282 (2)0.7860 (4)0.0628 (12)
C160.3841 (4)0.0665 (2)0.8162 (4)0.0704 (13)
H16A0.38380.03600.76460.084*
C170.3936 (4)0.0501 (2)0.9204 (4)0.0758 (14)
H17A0.39990.00880.93950.091*
C180.3939 (4)0.0952 (2)0.9963 (4)0.0769 (14)
C190.3828 (4)0.1565 (2)0.9695 (4)0.0742 (14)
H19A0.38170.18671.02180.089*
C200.3733 (4)0.1726 (2)0.8645 (4)0.0688 (13)
H20A0.36580.21400.84600.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.190 (2)0.1074 (13)0.0734 (10)0.0265 (13)0.0230 (11)0.0125 (9)
O10.192 (5)0.091 (3)0.073 (3)0.024 (3)0.040 (3)0.009 (2)
O20.113 (3)0.066 (2)0.078 (2)0.005 (2)0.022 (2)0.0022 (18)
O30.140 (4)0.064 (2)0.079 (2)0.014 (2)0.006 (3)0.0007 (19)
O1W0.169 (7)0.078 (4)0.107 (5)0.0000.033 (5)0.000
N10.059 (2)0.064 (2)0.070 (3)0.0050 (19)0.0088 (19)0.009 (2)
N20.067 (3)0.061 (2)0.073 (3)0.001 (2)0.009 (2)0.006 (2)
N30.065 (3)0.062 (2)0.068 (2)0.0007 (19)0.0080 (19)0.0076 (19)
C10.093 (4)0.066 (3)0.075 (3)0.008 (3)0.013 (3)0.002 (3)
C20.068 (3)0.061 (3)0.067 (3)0.004 (2)0.008 (2)0.009 (2)
C30.094 (4)0.065 (3)0.079 (4)0.001 (3)0.008 (3)0.013 (3)
C40.100 (4)0.055 (3)0.089 (4)0.001 (3)0.003 (3)0.007 (3)
C50.090 (4)0.057 (3)0.091 (4)0.005 (3)0.000 (3)0.008 (3)
C60.077 (3)0.066 (3)0.064 (3)0.002 (3)0.006 (2)0.002 (2)
C70.054 (3)0.061 (3)0.072 (3)0.000 (2)0.007 (2)0.007 (2)
C80.065 (3)0.063 (3)0.067 (3)0.002 (2)0.013 (2)0.006 (2)
C90.105 (4)0.070 (3)0.066 (3)0.009 (3)0.020 (3)0.002 (3)
C100.121 (5)0.070 (3)0.074 (3)0.016 (3)0.011 (3)0.005 (3)
C110.089 (4)0.057 (3)0.076 (3)0.001 (3)0.013 (3)0.003 (2)
C120.058 (3)0.062 (3)0.069 (3)0.003 (2)0.013 (2)0.001 (2)
C130.055 (3)0.063 (3)0.072 (3)0.005 (2)0.006 (2)0.003 (2)
C140.063 (3)0.073 (3)0.070 (3)0.002 (3)0.007 (2)0.003 (2)
C150.054 (3)0.064 (3)0.070 (3)0.007 (2)0.004 (2)0.009 (2)
C160.079 (3)0.058 (3)0.074 (3)0.004 (2)0.012 (3)0.001 (2)
C170.094 (4)0.059 (3)0.075 (3)0.006 (3)0.010 (3)0.008 (2)
C180.090 (4)0.071 (3)0.070 (3)0.005 (3)0.011 (3)0.002 (3)
C190.085 (4)0.064 (3)0.074 (3)0.005 (3)0.012 (3)0.005 (3)
C200.071 (3)0.054 (3)0.081 (3)0.002 (2)0.007 (3)0.002 (2)
Geometric parameters (Å, º) top
Cl—C181.730 (5)C6—H6A0.9300
O1—C11.207 (6)C8—C131.389 (6)
O2—C11.311 (6)C8—C91.403 (7)
O2—H2O0.8200C9—C101.364 (7)
O3—C111.333 (6)C9—H9A0.9300
O3—H3O0.8200C10—C111.383 (7)
O1W—H1W10.852 (10)C10—H10A0.9300
N1—N21.269 (5)C11—C121.409 (7)
N1—C71.426 (6)C12—C131.396 (6)
N2—C81.411 (6)C12—C141.438 (6)
N3—C141.287 (6)C13—H13A0.9300
N3—C151.407 (6)C14—H14A0.9300
C1—C21.487 (7)C15—C201.385 (6)
C2—C31.383 (6)C15—C161.395 (6)
C2—C71.404 (6)C16—C171.369 (6)
C3—C41.378 (7)C16—H16A0.9300
C3—H3A0.9300C17—C181.371 (7)
C4—C51.385 (7)C17—H17A0.9300
C4—H4A0.9300C18—C191.378 (7)
C5—C61.379 (6)C19—C201.378 (6)
C5—H5A0.9300C19—H19A0.9300
C6—C71.395 (6)C20—H20A0.9300
C1—O2—H2O109.5C9—C10—H10A119.6
C11—O3—H3O109.5C11—C10—H10A119.6
N2—N1—C7114.2 (4)O3—C11—C10118.6 (5)
N1—N2—C8114.3 (4)O3—C11—C12121.1 (5)
C14—N3—C15123.0 (4)C10—C11—C12120.2 (5)
O1—C1—O2118.6 (5)C13—C12—C11118.2 (5)
O1—C1—C2122.1 (5)C13—C12—C14120.5 (5)
O2—C1—C2119.2 (5)C11—C12—C14121.2 (5)
C3—C2—C7118.4 (5)C8—C13—C12121.3 (5)
C3—C2—C1117.3 (5)C8—C13—H13A119.4
C7—C2—C1124.3 (4)C12—C13—H13A119.4
C4—C3—C2121.4 (5)N3—C14—C12120.3 (5)
C4—C3—H3A119.3N3—C14—H14A119.8
C2—C3—H3A119.3C12—C14—H14A119.8
C3—C4—C5120.0 (5)C20—C15—C16118.2 (5)
C3—C4—H4A120.0C20—C15—N3125.5 (4)
C5—C4—H4A120.0C16—C15—N3116.3 (4)
C6—C5—C4120.0 (5)C17—C16—C15121.3 (5)
C6—C5—H5A120.0C17—C16—H16A119.4
C4—C5—H5A120.0C15—C16—H16A119.4
C5—C6—C7120.1 (5)C16—C17—C18119.2 (5)
C5—C6—H6A120.0C16—C17—H17A120.4
C7—C6—H6A120.0C18—C17—H17A120.4
C6—C7—C2120.1 (4)C17—C18—C19121.2 (5)
C6—C7—N1122.6 (4)C17—C18—Cl120.2 (4)
C2—C7—N1117.1 (4)C19—C18—Cl118.7 (4)
C13—C8—C9119.0 (5)C20—C19—C18119.2 (5)
C13—C8—N2114.9 (4)C20—C19—H19A120.4
C9—C8—N2126.1 (4)C18—C19—H19A120.4
C10—C9—C8120.4 (5)C19—C20—C15120.9 (5)
C10—C9—H9A119.8C19—C20—H20A119.5
C8—C9—H9A119.8C15—C20—H20A119.5
C9—C10—C11120.9 (5)
C7—N1—N2—C8174.3 (4)C9—C10—C11—C120.4 (9)
O1—C1—C2—C34.9 (9)O3—C11—C12—C13179.8 (5)
O2—C1—C2—C3172.0 (5)C10—C11—C12—C131.4 (8)
O1—C1—C2—C7174.1 (6)O3—C11—C12—C142.3 (8)
O2—C1—C2—C79.0 (8)C10—C11—C12—C14178.8 (5)
C7—C2—C3—C41.3 (8)C9—C8—C13—C120.0 (7)
C1—C2—C3—C4179.7 (5)N2—C8—C13—C12177.7 (4)
C2—C3—C4—C50.4 (9)C11—C12—C13—C81.2 (7)
C3—C4—C5—C60.1 (9)C14—C12—C13—C8178.6 (4)
C4—C5—C6—C70.2 (8)C15—N3—C14—C12179.2 (4)
C5—C6—C7—C21.1 (8)C13—C12—C14—N3177.9 (4)
C5—C6—C7—N1177.6 (5)C11—C12—C14—N30.5 (7)
C3—C2—C7—C61.6 (7)C14—N3—C15—C2021.2 (7)
C1—C2—C7—C6179.4 (5)C14—N3—C15—C16161.4 (5)
C3—C2—C7—N1178.3 (5)C20—C15—C16—C171.4 (8)
C1—C2—C7—N12.7 (7)N3—C15—C16—C17179.0 (4)
N2—N1—C7—C614.7 (6)C15—C16—C17—C180.1 (8)
N2—N1—C7—C2168.7 (4)C16—C17—C18—C191.3 (9)
N1—N2—C8—C13177.0 (4)C16—C17—C18—Cl179.2 (4)
N1—N2—C8—C95.5 (7)C17—C18—C19—C201.3 (9)
C13—C8—C9—C101.0 (8)Cl—C18—C19—C20179.2 (4)
N2—C8—C9—C10176.4 (5)C18—C19—C20—C150.0 (8)
C8—C9—C10—C110.9 (9)C16—C15—C20—C191.4 (7)
C9—C10—C11—O3179.2 (5)N3—C15—C20—C19178.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···N10.821.832.580 (5)152
O3—H3O···N30.821.812.544 (5)148
O1W—H1W1···O10.85 (1)2.05 (3)2.875 (5)164 (8)
C5—H5A···O1i0.932.563.457 (7)161
C14—H14A···O1Wii0.932.473.364 (7)162
C19—H19A···O2ii0.932.593.355 (6)140
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y, z+1.
 

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