(Z)-6-[(2-Fluorophenyliminio)methyl­ene]-2,3-dihydroxy­phenolate

Petek, H.; Albayrak, Ç.; Ağar, E.; Kalkan, H.

doi:10.1107/S1600536806029606

(Z)-6-[(2-Fluorophenyliminio)methylene]-2,3-dihydroxyphenolate

H. Petek, Ç. Albayrak, E. Ağar and H. Kalkan

The title compound, C₁₃H₁₀FNO₃, crystallizes in a zwitterionic form. The dihedral angle between the aromatic rings is 21.69 (9)°. O—H

O hydrogen bonds generate a centrosymmetric R₂²(10) dimer and the dimers are linked by O—H

O hydrogen bonds into sheets parallel to (10 $\overline{1}$ ).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029606/ci2106sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029606/ci2106Isup2.hkl Contains datablock I

CCDC reference: 620732

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.051
wR factor = 0.124
Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.85

Author Response: The crystal which was used for collecting intensity data was in poor quality and beside this it was a non-merohedral twin (twin lattice quasi-crystal=TLQS) with two reciprocal lattice differently oriented giving rise to double diffraction spot sets. We were aware of the twin character of this crystal at the data collection stage but we were unable to find pure crystals.The two data sets of the twin parts were integrated separately and then scaled to give the used hkl set. However, because the partial overlapped reflections could not be integrated seperately, the completeness of data value decreased to %85.


Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           27.24
           From the CIF: _diffrn_reflns_theta_full          27.24
           From the CIF: _reflns_number_total               2076
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2435
           Completeness (_total/calc)             85.26%
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.85
PLAT353_ALERT_3_B Long    N-H Bond (0.87A)   N1     -   H1     ...       1.11 Ang.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.125
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.77 mm
PLAT230_ALERT_2_C Hirshfeld Test Diff for    F1     -   C13     ..       5.58 su
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O1

   1 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(Z)-6-[(2-Fluorophenylininio)methylene]-2,3-dihydroxyphenolate top

Crystal data top

C₁₃H₁₀FNO₃	F(000) = 512
M_r = 247.22	D_x = 1.506 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7428 reflections
a = 11.5456 (11) Å	θ = 2.5–27.2°
b = 6.8521 (4) Å	µ = 0.12 mm⁻¹
c = 14.0447 (14) Å	T = 296 K
β = 101.185 (8)°	Plate, red
V = 1089.99 (16) Å³	0.77 × 0.36 × 0.06 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	2076 independent reflections
Radiation source: fine-focus sealed tube	1263 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.125
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.2°, θ_min = 2.5°
ω scans	h = −14→14
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −8→8
T_min = 0.937, T_max = 0.992	l = −18→18
12517 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	All H-atom parameters refined
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0678P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.001
2076 reflections	Δρ_max = 0.21 e Å⁻³
204 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (6)

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

	x	y	z	U_iso*/U_eq
H7	0.7305 (18)	0.608 (3)	0.5133 (15)	0.063 (6)*
H11	0.292 (3)	0.338 (4)	0.263 (2)	0.097 (8)*
H9	0.576 (2)	0.636 (4)	0.3921 (18)	0.081 (8)*
H12	0.388 (3)	0.038 (4)	0.336 (2)	0.099 (9)*
H10	0.396 (3)	0.628 (4)	0.295 (2)	0.110 (10)*
H4	1.093 (2)	0.715 (3)	0.7110 (16)	0.072 (6)*
H5	0.9003 (19)	0.746 (3)	0.6178 (14)	0.054 (6)*
H3	1.248 (2)	0.505 (4)	0.761 (2)	0.096 (9)*
H2	1.087 (2)	0.019 (4)	0.583 (2)	0.101 (9)*
H1	0.771 (3)	0.208 (5)	0.486 (2)	0.143 (12)*
O1	0.89164 (12)	0.12243 (19)	0.53201 (10)	0.0595 (4)
O3	1.22224 (13)	0.3971 (3)	0.73077 (12)	0.0691 (5)
N1	0.71082 (14)	0.3350 (2)	0.47091 (12)	0.0549 (4)
C1	0.94255 (17)	0.2797 (3)	0.57624 (13)	0.0500 (5)
O2	1.11948 (13)	0.0956 (2)	0.63306 (11)	0.0683 (5)
C6	0.88363 (17)	0.4626 (3)	0.57110 (13)	0.0515 (5)
C8	0.59542 (17)	0.3447 (3)	0.41479 (14)	0.0556 (5)
C2	1.05778 (18)	0.2667 (3)	0.62917 (13)	0.0522 (5)
C4	1.05304 (18)	0.6063 (3)	0.67508 (15)	0.0575 (5)
C5	0.94209 (19)	0.6229 (3)	0.62126 (15)	0.0571 (5)
C7	0.76767 (18)	0.4819 (3)	0.51546 (14)	0.0550 (5)
C3	1.11110 (17)	0.4266 (3)	0.67934 (13)	0.0525 (5)
F1	0.58846 (13)	0.0059 (2)	0.43003 (12)	0.0936 (5)
C13	0.53358 (19)	0.1732 (3)	0.39512 (16)	0.0638 (6)
C9	0.5406 (2)	0.5140 (4)	0.37629 (17)	0.0696 (6)
C11	0.3687 (2)	0.3357 (5)	0.30473 (19)	0.0852 (8)
C12	0.4211 (2)	0.1655 (5)	0.3417 (2)	0.0815 (8)
C10	0.4276 (2)	0.5084 (5)	0.32190 (19)	0.0818 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0610 (9)	0.0471 (8)	0.0634 (8)	0.0008 (6)	−0.0050 (6)	−0.0086 (6)
O3	0.0537 (9)	0.0743 (10)	0.0706 (9)	−0.0018 (7)	−0.0092 (7)	−0.0123 (8)
N1	0.0494 (9)	0.0553 (10)	0.0564 (9)	0.0042 (7)	0.0011 (7)	−0.0016 (7)
C1	0.0536 (11)	0.0472 (10)	0.0469 (9)	−0.0014 (8)	0.0035 (8)	−0.0035 (8)
O2	0.0657 (10)	0.0590 (9)	0.0688 (9)	0.0163 (7)	−0.0148 (7)	−0.0131 (7)
C6	0.0528 (11)	0.0484 (11)	0.0512 (10)	0.0013 (8)	0.0046 (8)	−0.0017 (8)
C8	0.0482 (11)	0.0656 (13)	0.0521 (11)	0.0043 (9)	0.0073 (8)	−0.0003 (9)
C2	0.0528 (12)	0.0513 (11)	0.0494 (10)	0.0068 (8)	0.0021 (8)	−0.0015 (8)
C4	0.0617 (13)	0.0520 (11)	0.0562 (11)	−0.0064 (9)	0.0050 (9)	−0.0069 (9)
C5	0.0635 (12)	0.0477 (11)	0.0586 (11)	0.0030 (9)	0.0080 (9)	−0.0038 (9)
C7	0.0570 (12)	0.0502 (10)	0.0558 (11)	0.0059 (9)	0.0059 (9)	−0.0006 (9)
C3	0.0480 (11)	0.0600 (12)	0.0471 (10)	−0.0034 (8)	0.0035 (8)	−0.0019 (8)
F1	0.0876 (10)	0.0613 (8)	0.1230 (12)	−0.0021 (7)	−0.0015 (9)	−0.0059 (8)
C13	0.0613 (13)	0.0628 (14)	0.0649 (13)	0.0026 (10)	0.0061 (10)	−0.0053 (10)
C9	0.0557 (13)	0.0721 (15)	0.0772 (15)	0.0041 (11)	0.0035 (11)	0.0113 (12)
C11	0.0517 (14)	0.124 (3)	0.0753 (16)	0.0032 (15)	0.0004 (12)	−0.0032 (15)
C12	0.0625 (15)	0.095 (2)	0.0836 (17)	−0.0147 (14)	0.0069 (12)	−0.0195 (15)
C10	0.0608 (15)	0.101 (2)	0.0793 (16)	0.0155 (15)	0.0044 (12)	0.0182 (15)

Geometric parameters (Å, º) top

O1—C1	1.323 (2)	C4—C5	1.360 (3)
O3—C3	1.360 (2)	C4—C3	1.398 (3)
O3—H3	0.88 (3)	C4—H4	0.96 (2)
N1—C7	1.295 (2)	C5—H5	0.97 (2)
N1—C8	1.412 (2)	C7—H7	0.96 (2)
N1—H1	1.11 (3)	F1—C13	1.355 (3)
C1—C2	1.395 (3)	C13—C12	1.369 (3)
C1—C6	1.421 (3)	C9—C10	1.379 (3)
O2—C2	1.368 (2)	C9—H9	0.94 (3)
O2—H2	0.90 (3)	C11—C10	1.362 (4)
C6—C5	1.405 (3)	C11—C12	1.369 (4)
C6—C7	1.419 (3)	C11—H11	0.96 (3)
C8—C13	1.375 (3)	C12—H12	0.95 (3)
C8—C9	1.381 (3)	C10—H10	0.95 (3)
C2—C3	1.381 (3)

C3—O3—H3	109.3 (18)	C6—C5—H5	118.0 (11)
C7—N1—C8	124.64 (17)	N1—C7—C6	121.95 (18)
C7—N1—H1	106.1 (17)	N1—C7—H7	120.1 (12)
C8—N1—H1	129.3 (17)	C6—C7—H7	118.0 (12)
O1—C1—C2	119.28 (17)	O3—C3—C2	115.75 (18)
O1—C1—C6	121.98 (16)	O3—C3—C4	123.29 (17)
C2—C1—C6	118.73 (16)	C2—C3—C4	120.95 (17)
C2—O2—H2	109.8 (17)	F1—C13—C12	119.5 (2)
C5—C6—C7	120.86 (18)	F1—C13—C8	117.53 (17)
C5—C6—C1	119.05 (17)	C12—C13—C8	122.9 (2)
C7—C6—C1	120.09 (16)	C10—C9—C8	120.4 (3)
C13—C8—C9	117.30 (19)	C10—C9—H9	118.6 (15)
C13—C8—N1	117.98 (17)	C8—C9—H9	120.6 (15)
C9—C8—N1	124.70 (19)	C10—C11—C12	120.3 (2)
O2—C2—C3	118.86 (17)	C10—C11—H11	117.7 (16)
O2—C2—C1	120.74 (16)	C12—C11—H11	121.9 (16)
C3—C2—C1	120.40 (17)	C11—C12—C13	118.5 (3)
C5—C4—C3	119.34 (18)	C11—C12—H12	127.6 (17)
C5—C4—H4	122.1 (13)	C13—C12—H12	113.9 (17)
C3—C4—H4	118.6 (13)	C11—C10—C9	120.5 (3)
C4—C5—C6	121.5 (2)	C11—C10—H10	122.6 (18)
C4—C5—H5	120.5 (11)	C9—C10—H10	116.8 (18)

O1—C1—C6—C5	178.9 (2)	C1—C2—C3—O3	178.23 (19)
C2—C1—C6—C5	−1.5 (3)	O2—C2—C3—C4	178.0 (2)
O1—C1—C6—C7	−1.5 (3)	C1—C2—C3—C4	−2.6 (3)
C2—C1—C6—C7	178.1 (2)	C5—C4—C3—O3	179.6 (2)
C7—N1—C8—C13	−161.7 (2)	C5—C4—C3—C2	0.5 (3)
C7—N1—C8—C9	19.7 (3)	C9—C8—C13—F1	177.9 (2)
O1—C1—C2—O2	2.1 (3)	N1—C8—C13—F1	−0.8 (3)
C6—C1—C2—O2	−177.50 (18)	C9—C8—C13—C12	−1.4 (4)
O1—C1—C2—C3	−177.27 (19)	N1—C8—C13—C12	179.8 (2)
C6—C1—C2—C3	3.1 (3)	C13—C8—C9—C10	1.1 (4)
C3—C4—C5—C6	1.1 (3)	N1—C8—C9—C10	179.7 (2)
C7—C6—C5—C4	179.8 (2)	C10—C11—C12—C13	−0.6 (4)
C1—C6—C5—C4	−0.6 (3)	F1—C13—C12—C11	−178.1 (2)
C8—N1—C7—C6	179.81 (19)	C8—C13—C12—C11	1.2 (4)
C5—C6—C7—N1	−178.0 (2)	C12—C11—C10—C9	0.3 (4)
C1—C6—C7—N1	2.4 (3)	C8—C9—C10—C11	−0.5 (4)
O2—C2—C3—O3	−1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	1.11 (3)	1.53 (3)	2.554 (2)	150 (3)
O3—H3···O2ⁱ	0.88 (3)	2.01 (3)	2.737 (2)	139 (2)
O2—H2···O1ⁱⁱ	0.90 (3)	1.94 (3)	2.740 (2)	147 (2)

Symmetry codes: (i) −x+5/2, y+1/2, −z+3/2; (ii) −x+2, −y, −z+1.

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(Z)-6-[(2-Fluorophenyliminio)methyl­ene]-2,3-dihydroxy­phenolate

Supporting information

Key indicators

checkCIF/PLATON results

(Z)-6-[(2-Fluorophenyliminio)methylene]-2,3-dihydroxyphenolate