In the title compound, C
9H
7ClN
2O, the dihedral angle between the aromatic ring planes is 11.0 (2)°. In the crystal, inversion dimers linked by pairs of O—H

N hydrogen bonds generate
R22(8) loops.
Supporting information
CCDC reference: 766845
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.059
- wR factor = 0.146
- Data-to-parameter ratio = 11.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.583 82
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 24.50
From the CIF: _diffrn_reflns_theta_full 24.50
From the CIF: _reflns_number_total 1357
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 1442
Completeness (_total/calc) 94.11%
THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590
Calculated sin(theta_max)/wavelength = 0.5835
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94
PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6].. 24.50 Deg.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 6
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 3
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 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
8 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
A mixture of p-Chlorophenylhydrazing hydrochloride (0.02 mol) and methyl
acrylate (0.02 mol) was stirred in ethanol (30 ml) at 353 K for 2 h to afford
the title compound (yield 50%). Colourless bars of (I)
were obtained by recrystallization from acetone at room temperature.
The O-bound H atom was located in a difference map and freely refined.
The C-bound H atoms were positioned geometrically and allowed to ride on their
parent atoms, with C—H = 0.93–0.96 Å and
with Uiso(H) = 1.2Ueq of the parent atoms.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
1-(4-Chlorophenyl)-1
H-pyrazol-3-ol
top
Crystal data top
C9H7ClN2O | F(000) = 400 |
Mr = 194.62 | Dx = 1.494 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1171 reflections |
a = 9.6461 (19) Å | θ = 3.5–27.5° |
b = 13.833 (3) Å | µ = 0.40 mm−1 |
c = 6.5045 (13) Å | T = 293 K |
β = 94.33 (3)° | Bar, colourless |
V = 865.4 (3) Å3 | 0.11 × 0.09 × 0.08 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD diffractometer | 1171 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 24.5°, θmin = 3.5° |
ω scans | h = −11→11 |
5771 measured reflections | k = −16→16 |
1357 independent reflections | l = −7→7 |
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)] = 0.059 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.0166P)2 + 1.7755P] where P = (Fo2 + 2Fc2)/3 |
S = 1.24 | (Δ/σ)max < 0.001 |
1357 reflections | Δρmax = 0.23 e Å−3 |
122 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.049 (5) |
Crystal data top
C9H7ClN2O | V = 865.4 (3) Å3 |
Mr = 194.62 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.6461 (19) Å | µ = 0.40 mm−1 |
b = 13.833 (3) Å | T = 293 K |
c = 6.5045 (13) Å | 0.11 × 0.09 × 0.08 mm |
β = 94.33 (3)° | |
Data collection top
Bruker SMART CCD diffractometer | 1171 reflections with I > 2σ(I) |
5771 measured reflections | Rint = 0.038 |
1357 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.24 | Δρmax = 0.23 e Å−3 |
1357 reflections | Δρmin = −0.32 e Å−3 |
122 parameters | |
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 | Uiso*/Ueq | |
Cl1 | 1.03021 (14) | 0.13637 (11) | −0.3127 (2) | 0.0771 (6) | |
O1 | 0.3291 (3) | 0.0636 (2) | 0.5246 (5) | 0.0508 (8) | |
H1 | 0.377 (5) | 0.019 (3) | 0.588 (7) | 0.061* | |
N1 | 0.5047 (3) | 0.1156 (2) | 0.1005 (5) | 0.0361 (8) | |
N2 | 0.5009 (3) | 0.0759 (2) | 0.2928 (5) | 0.0380 (8) | |
C1 | 0.3807 (4) | 0.1554 (3) | 0.0396 (7) | 0.0458 (10) | |
H1A | 0.3588 | 0.1868 | −0.0851 | 0.055* | |
C2 | 0.2936 (4) | 0.1420 (3) | 0.1900 (6) | 0.0443 (10) | |
H2B | 0.2015 | 0.1617 | 0.1908 | 0.053* | |
C3 | 0.3726 (4) | 0.0919 (3) | 0.3442 (6) | 0.0386 (9) | |
C4 | 0.6308 (4) | 0.1525 (3) | −0.1997 (6) | 0.0423 (10) | |
H4A | 0.5476 | 0.1707 | −0.2710 | 0.051* | |
C5 | 0.7541 (5) | 0.1583 (3) | −0.2943 (6) | 0.0467 (11) | |
H5A | 0.7539 | 0.1807 | −0.4292 | 0.056* | |
C6 | 0.8760 (5) | 0.1314 (3) | −0.1905 (7) | 0.0475 (11) | |
C7 | 0.8777 (4) | 0.0988 (3) | 0.0093 (7) | 0.0489 (11) | |
H7A | 0.9613 | 0.0808 | 0.0792 | 0.059* | |
C8 | 0.7556 (4) | 0.0929 (3) | 0.1066 (6) | 0.0414 (10) | |
H8A | 0.7570 | 0.0710 | 0.2419 | 0.050* | |
C9 | 0.6311 (4) | 0.1195 (2) | 0.0022 (6) | 0.0339 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0584 (9) | 0.1009 (11) | 0.0757 (10) | −0.0004 (7) | 0.0298 (7) | 0.0190 (7) |
O1 | 0.0422 (17) | 0.065 (2) | 0.0469 (18) | 0.0123 (14) | 0.0141 (15) | 0.0138 (14) |
N1 | 0.0355 (18) | 0.0400 (17) | 0.0322 (17) | 0.0012 (13) | −0.0011 (15) | 0.0040 (13) |
N2 | 0.0361 (19) | 0.0440 (18) | 0.0338 (18) | 0.0036 (13) | 0.0011 (15) | 0.0065 (14) |
C1 | 0.044 (2) | 0.051 (2) | 0.040 (2) | 0.0064 (18) | −0.009 (2) | 0.0060 (18) |
C2 | 0.034 (2) | 0.051 (2) | 0.048 (3) | 0.0073 (17) | 0.000 (2) | −0.0012 (18) |
C3 | 0.036 (2) | 0.038 (2) | 0.042 (2) | 0.0023 (16) | 0.0044 (19) | −0.0017 (16) |
C4 | 0.045 (2) | 0.045 (2) | 0.035 (2) | −0.0016 (17) | −0.007 (2) | 0.0043 (16) |
C5 | 0.058 (3) | 0.048 (2) | 0.035 (2) | −0.0062 (19) | 0.007 (2) | 0.0046 (17) |
C6 | 0.048 (3) | 0.045 (2) | 0.052 (3) | −0.0038 (18) | 0.015 (2) | 0.0037 (19) |
C7 | 0.039 (2) | 0.052 (2) | 0.055 (3) | 0.0012 (18) | 0.004 (2) | 0.008 (2) |
C8 | 0.042 (2) | 0.047 (2) | 0.035 (2) | 0.0014 (17) | 0.0012 (19) | 0.0063 (17) |
C9 | 0.039 (2) | 0.0323 (19) | 0.030 (2) | −0.0027 (15) | −0.0007 (17) | −0.0013 (14) |
Geometric parameters (Å, º) top
Cl1—C6 | 1.740 (4) | C4—C5 | 1.382 (6) |
O1—C3 | 1.334 (5) | C4—C9 | 1.390 (5) |
O1—H1 | 0.86 (5) | C4—H4A | 0.9300 |
N1—C1 | 1.349 (5) | C5—C6 | 1.363 (6) |
N1—N2 | 1.369 (4) | C5—H5A | 0.9300 |
N1—C9 | 1.420 (5) | C6—C7 | 1.374 (6) |
N2—C3 | 1.325 (5) | C7—C8 | 1.381 (6) |
C1—C2 | 1.349 (6) | C7—H7A | 0.9300 |
C1—H1A | 0.9300 | C8—C9 | 1.384 (5) |
C2—C3 | 1.396 (5) | C8—H8A | 0.9300 |
C2—H2B | 0.9300 | | |
| | | |
C3—O1—H1 | 116 (3) | C9—C4—H4A | 120.0 |
C1—N1—N2 | 110.4 (3) | C6—C5—C4 | 120.2 (4) |
C1—N1—C9 | 128.7 (3) | C6—C5—H5A | 119.9 |
N2—N1—C9 | 120.6 (3) | C4—C5—H5A | 119.9 |
C3—N2—N1 | 104.7 (3) | C5—C6—C7 | 120.4 (4) |
N1—C1—C2 | 108.5 (4) | C5—C6—Cl1 | 119.9 (3) |
N1—C1—H1A | 125.7 | C7—C6—Cl1 | 119.7 (4) |
C2—C1—H1A | 125.7 | C6—C7—C8 | 120.2 (4) |
C1—C2—C3 | 104.7 (4) | C6—C7—H7A | 119.9 |
C1—C2—H2B | 127.7 | C8—C7—H7A | 119.9 |
C3—C2—H2B | 127.7 | C7—C8—C9 | 119.9 (4) |
N2—C3—O1 | 122.3 (3) | C7—C8—H8A | 120.1 |
N2—C3—C2 | 111.8 (3) | C9—C8—H8A | 120.1 |
O1—C3—C2 | 125.9 (4) | C8—C9—C4 | 119.4 (4) |
C5—C4—C9 | 119.9 (4) | C8—C9—N1 | 120.8 (3) |
C5—C4—H4A | 120.0 | C4—C9—N1 | 119.8 (3) |
| | | |
C1—N1—N2—C3 | 0.5 (4) | C5—C6—C7—C8 | 0.2 (6) |
C9—N1—N2—C3 | 174.5 (3) | Cl1—C6—C7—C8 | −178.8 (3) |
N2—N1—C1—C2 | −0.3 (4) | C6—C7—C8—C9 | 0.2 (6) |
C9—N1—C1—C2 | −173.7 (3) | C7—C8—C9—C4 | −0.3 (6) |
N1—C1—C2—C3 | −0.1 (5) | C7—C8—C9—N1 | −178.9 (3) |
N1—N2—C3—O1 | −179.6 (3) | C5—C4—C9—C8 | 0.1 (6) |
N1—N2—C3—C2 | −0.6 (4) | C5—C4—C9—N1 | 178.6 (3) |
C1—C2—C3—N2 | 0.4 (5) | C1—N1—C9—C8 | 165.9 (4) |
C1—C2—C3—O1 | 179.4 (4) | N2—N1—C9—C8 | −6.9 (5) |
C9—C4—C5—C6 | 0.3 (6) | C1—N1—C9—C4 | −12.7 (6) |
C4—C5—C6—C7 | −0.4 (6) | N2—N1—C9—C4 | 174.5 (3) |
C4—C5—C6—Cl1 | 178.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.86 (4) | 1.89 (4) | 2.744 (4) | 173 (4) |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data |
Chemical formula | C9H7ClN2O |
Mr | 194.62 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.6461 (19), 13.833 (3), 6.5045 (13) |
β (°) | 94.33 (3) |
V (Å3) | 865.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.11 × 0.09 × 0.08 |
|
Data collection |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5771, 1357, 1171 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.583 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.146, 1.24 |
No. of reflections | 1357 |
No. of parameters | 122 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.32 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.86 (4) | 1.89 (4) | 2.744 (4) | 173 (4) |
Symmetry code: (i) −x+1, −y, −z+1. |
p-Chlorophenyl hydrazine hydrochloride is an important biologically active compound used in herbicides and plant growth substances (Shi et al.,1995; Xu, et al.,2002). Here we report the crystal structure of the title compound (I).
In the title compound (I) (Fig. 1), the The dihedral angle between the pheny ring (C4,C5,C6,C7,C8 and C9) and ring 1(N1,N2,C1,C2 and C3) is 11.0 (2)°. The C—N bonds length in the range of (1.321 (5) Å-1.416 (5) Å) are in agreement with that observed before (Jian et al., 2005).