(E)-2,4-Dichloro-6-[(2-hydroxy­ethyl­iminio)meth­yl]phenolate

The mol­ecule of the title compound, C₉H₉Cl₂NO₂, is a zwitterion with cationic iminium and an anionic phenolate group, which form an intra­molecular N—H...O hydrogen bond closing a six-membered pseudocycle. Inter­molecular O—H...O hydrogen bonds link the mol­ecules into infinite chains running along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.073
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.20
           From the CIF: _reflns_number_total               1730
           Count of symmetry unique reflns          990
           Completeness (_total/calc)            174.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       740
           Fraction of Friedel pairs measured     0.747
           Are heavy atom types Z>Si present        yes

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL(Bruker, 2002); software used to prepare material for publication: SHELXL97.

(E)-2,4-dichloro-6-[(2-hydroxyethyliminio)methyl]phenolate

Crystal data

C9H9Cl2NO2	Dx = 1.596 Mg m^−3
Mr = 234.07	Melting point: 409.7 K
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 250 reflections
a = 18.619 (3) Å	θ = 2.0–27.5°
b = 21.447 (4) Å	µ = 0.64 mm^−1
c = 4.8779 (9) Å	T = 295 K
V = 1947.9 (6) Å^3	Block, orange
Z = 8	0.28 × 0.23 × 0.15 mm
F(000) = 960

Data collection

Siemens SMART CCD area detector diffractometer	1730 independent reflections
Radiation source: fine-focus sealed tube	1690 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω and φ scans	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −15→22
Tmin = 0.834, Tmax = 0.902	k = −23→25
5027 measured reflections	l = −5→5

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	All H-atom parameters refined
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 1.0811P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
1730 reflections	Δρmax = 0.20 e Å^−3
163 parameters	Δρmin = −0.19 e Å^−3
1 restraint	Absolute structure: Flack (1983), 740 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.44604 (11)	0.56740 (11)	0.2954 (5)	0.0348 (5)
Cl1	0.68249 (3)	0.61415 (3)	0.89565 (15)	0.03919 (17)
Cl2	0.65019 (4)	0.80138 (3)	0.17326 (17)	0.0494 (2)
O1	0.54686 (8)	0.56780 (7)	0.6568 (4)	0.0396 (4)
O2	0.28677 (9)	0.58035 (8)	0.3931 (5)	0.0422 (4)
C1	0.53147 (12)	0.64954 (10)	0.3328 (5)	0.0325 (5)
C2	0.56863 (12)	0.61922 (10)	0.5514 (5)	0.0307 (5)
C3	0.63230 (11)	0.64990 (10)	0.6408 (5)	0.0315 (5)
C4	0.65576 (13)	0.70519 (11)	0.5319 (5)	0.0345 (6)
C5	0.61663 (12)	0.73280 (10)	0.3204 (5)	0.0345 (6)
C6	0.55630 (14)	0.70623 (11)	0.2209 (6)	0.0357 (6)
C7	0.47060 (13)	0.61942 (11)	0.2113 (6)	0.0359 (6)
C8	0.38820 (13)	0.53270 (12)	0.1588 (6)	0.0404 (6)
C9	0.32451 (14)	0.52399 (12)	0.3444 (6)	0.0391 (6)
H9B	0.2941 (16)	0.4949 (12)	0.262 (6)	0.046 (8)*
H4	0.6999 (15)	0.7229 (11)	0.602 (7)	0.043 (7)*
H9A	0.3408 (16)	0.5101 (14)	0.515 (7)	0.043 (8)*
H8B	0.3771 (15)	0.5576 (13)	−0.005 (6)	0.046 (8)*
H6	0.5321 (16)	0.7221 (12)	0.078 (7)	0.044 (8)*
H2	0.2667 (16)	0.5894 (12)	0.256 (7)	0.045 (9)*
H7	0.4505 (17)	0.6384 (12)	0.057 (8)	0.057 (10)*
H8A	0.4081 (16)	0.4901 (13)	0.111 (7)	0.058 (9)*
H1	0.4721 (19)	0.5530 (14)	0.401 (11)	0.071 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0277 (11)	0.0406 (12)	0.0361 (12)	0.0016 (9)	−0.0033 (9)	−0.0040 (8)
Cl1	0.0353 (3)	0.0473 (3)	0.0350 (3)	−0.0005 (2)	−0.0062 (3)	0.0058 (3)
Cl2	0.0552 (4)	0.0356 (3)	0.0575 (4)	−0.0058 (3)	0.0059 (4)	0.0104 (3)
O1	0.0393 (9)	0.0386 (8)	0.0411 (10)	−0.0085 (7)	−0.0048 (8)	0.0090 (8)
O2	0.0405 (9)	0.0456 (9)	0.0406 (10)	0.0051 (8)	0.0002 (10)	−0.0074 (10)
C1	0.0277 (11)	0.0355 (12)	0.0343 (14)	0.0030 (9)	0.0004 (10)	0.0001 (10)
C2	0.0265 (10)	0.0334 (11)	0.0320 (13)	0.0022 (9)	0.0046 (9)	−0.0014 (10)
C3	0.0317 (11)	0.0359 (12)	0.0269 (11)	0.0047 (9)	0.0029 (10)	−0.0018 (10)
C4	0.0328 (14)	0.0348 (13)	0.0360 (13)	−0.0013 (10)	0.0045 (10)	−0.0049 (10)
C5	0.0359 (12)	0.0284 (11)	0.0391 (15)	−0.0001 (10)	0.0071 (11)	0.0021 (10)
C6	0.0359 (14)	0.0347 (13)	0.0366 (14)	0.0061 (10)	0.0016 (11)	0.0048 (11)
C7	0.0310 (13)	0.0413 (13)	0.0355 (15)	0.0055 (10)	−0.0022 (11)	−0.0019 (11)
C8	0.0351 (13)	0.0436 (14)	0.0424 (15)	−0.0039 (10)	−0.0018 (12)	−0.0130 (14)
C9	0.0366 (13)	0.0388 (13)	0.0417 (18)	−0.0065 (11)	−0.0055 (12)	−0.0032 (12)

Geometric parameters (Å, º)

Cl1—C3	1.734 (2)	C3—C4	1.371 (3)
Cl2—C5	1.752 (2)	C4—C5	1.395 (4)
O1—C2	1.283 (3)	C4—H4	0.97 (3)
O2—C9	1.418 (3)	C5—C6	1.350 (4)
N1—C7	1.274 (3)	C6—H6	0.90 (3)
N1—C8	1.469 (3)	C7—H7	0.93 (4)
N1—H1	0.77 (4)	C8—C9	1.503 (4)
O2—H2	0.79 (3)	C8—H8B	0.98 (3)
C1—C6	1.411 (3)	C8—H8A	1.01 (3)
C1—C2	1.428 (3)	C9—H9B	0.93 (3)
C1—C7	1.433 (3)	C9—H9A	0.93 (3)
C2—C3	1.424 (3)
C7—N1—C8	124.1 (3)	C5—C6—C1	119.8 (2)
C7—N1—H1	110 (3)	C5—C6—H6	122.5 (19)
C8—N1—H1	124 (2)	C1—C6—H6	117.5 (19)
C9—O2—H2	108 (2)	N1—C7—C1	123.1 (2)
C6—C1—C2	121.5 (2)	N1—C7—H7	119.8 (18)
C6—C1—C7	119.2 (2)	C1—C7—H7	117.0 (18)
C2—C1—C7	119.1 (2)	N1—C8—C9	111.6 (2)
O1—C2—C3	122.5 (2)	N1—C8—H8B	104.4 (17)
O1—C2—C1	122.5 (2)	C9—C8—H8B	113.1 (17)
C3—C2—C1	114.9 (2)	N1—C8—H8A	107.0 (18)
C4—C3—C2	123.1 (2)	C9—C8—H8A	108.3 (17)
C4—C3—Cl1	119.25 (19)	H8B—C8—H8A	112 (2)
C2—C3—Cl1	117.63 (17)	O2—C9—C8	112.7 (2)
C3—C4—C5	119.2 (2)	O2—C9—H9B	109.9 (18)
C3—C4—H4	118.3 (17)	C8—C9—H9B	107.6 (18)
C5—C4—H4	122.5 (17)	O2—C9—H9A	106.5 (19)
C6—C5—C4	121.4 (2)	C8—C9—H9A	108.7 (19)
C6—C5—Cl2	120.3 (2)	H9B—C9—H9A	112 (3)
C4—C5—Cl2	118.24 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.77 (4)	1.89 (4)	2.575 (3)	147 (3)
O2—H2···O2^i	0.79 (3)	2.04 (3)	2.7970 (18)	160 (3)

Symmetry code: (i) −x+1/2, y, z−1/2.