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In the title compound, C16H14ClN5O·C2H6O, the main residue is approximately planar except for the aniline group. Classical intramolecular hydrogen bonds are observed from the amino N atom to the carbonyl O atom and from the carbox­amide N atom to the aniline N atom. Four further hydrogen bonds connect the residues to form layers parallel to (101).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020689/bt6501sup1.cif
Contains datablocks 4, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020689/bt65014sup2.hkl
Contains datablock 4

CCDC reference: 238053

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.083
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT420_ALERT_2_C D-H Without Acceptor N3 - H031 ... ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

5-Amino-3-anilino-N-(chlorophenyl)-1H-pyrazole-4-carboxamide ethanol solvate top
Crystal data top
C16H14ClN5O·C2H6OF(000) = 784
Mr = 373.84Dx = 1.382 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.6757 (10) ÅCell parameters from 63 reflections
b = 7.7798 (9) Åθ = 4.5–12.5°
c = 21.919 (2) ŵ = 0.24 mm1
β = 99.14 (1)°T = 173 K
V = 1797.3 (3) Å3Tablet, colourless
Z = 40.4 × 0.4 × 0.3 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.022
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.2°
Graphite monochromatorh = 1212
ω scansk = 94
4927 measured reflectionsl = 025
3167 independent reflections3 standard reflections every 247 reflections
2349 reflections with I > 2σ(I) intensity decay: none
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 0.93 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
3167 reflections(Δ/σ)max = 0.001
260 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.27 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.7737 (0.0015) x + 2.0537 (0.0022) y + 13.5119 (0.0046) z = 9.4223 (0.0013)

* -0.0203 (0.0014) C3 * 0.0704 (0.0015) C4 * 0.0405 (0.0015) C5 * 0.0243 (0.0015) C12 * 0.1520 (0.0015) C13 * 0.1260 (0.0015) C14 * -0.0298 (0.0015) C15 * -0.1946 (0.0016) C16 * -0.1700 (0.0016) C17 * -0.0418 (0.0014) N1 * -0.0890 (0.0013) N2 * 0.0324 (0.0014) N3 * -0.1171 (0.0012) N4 * 0.0803 (0.0014) N5 * 0.1400 (0.0011) O1 * -0.0034 (0.0008) Cl

Rms deviation of fitted atoms = 0.1015

- 6.6383 (0.0052) x + 4.4211 (0.0049) y + 13.8267 (0.0091) z = 2.9976 (0.0042)

Angle to previous plane (with approximate e.s.d.) = 81.55 (0.03)

* -0.0056 (0.0010) N4 * -0.0037 (0.0014) C18 * 0.0061 (0.0014) C19 * 0.0040 (0.0013) C20 * -0.0108 (0.0014) C21 * 0.0017 (0.0013) C22 * 0.0084 (0.0014) C23

Rms deviation of fitted atoms = 0.0064

============================================================================

Contacts:

3.6286 (0.0011) Cl - Cl_$5

101.82 (0.07) C15 - Cl - Cl_$5

$5 - x, -y + 2, -z + 1

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
Cl0.04477 (5)0.81766 (7)0.55036 (2)0.04214 (16)
O10.43047 (11)0.18838 (16)0.46327 (5)0.0275 (3)
N10.68056 (14)0.0993 (2)0.33798 (7)0.0285 (4)
H010.7241 (17)0.008 (3)0.3254 (8)0.033 (5)*
N20.67822 (13)0.25984 (19)0.31126 (6)0.0265 (4)
C30.60229 (15)0.3501 (2)0.34070 (7)0.0220 (4)
C40.55412 (15)0.2524 (2)0.38640 (7)0.0216 (4)
N30.59107 (18)0.0588 (2)0.41236 (8)0.0336 (4)
H0310.638 (2)0.137 (3)0.4083 (10)0.047 (7)*
H0320.5647 (19)0.052 (3)0.4476 (10)0.050 (7)*
N40.57055 (14)0.5226 (2)0.32321 (6)0.0240 (3)
H040.6374 (18)0.585 (2)0.3201 (8)0.030 (5)*
C50.60714 (16)0.0899 (2)0.38230 (7)0.0240 (4)
N50.41956 (13)0.4604 (2)0.42298 (7)0.0245 (3)
H050.4529 (17)0.525 (3)0.4001 (9)0.035 (6)*
C60.46426 (15)0.2960 (2)0.42783 (7)0.0219 (4)
C120.32742 (15)0.5377 (2)0.45327 (7)0.0220 (4)
C130.30879 (16)0.7143 (2)0.44522 (8)0.0262 (4)
H130.35690.77600.41960.031*
C140.22138 (16)0.8007 (2)0.47397 (8)0.0280 (4)
H140.20940.92100.46820.034*
C150.15153 (16)0.7103 (3)0.51121 (8)0.0281 (4)
C160.16619 (17)0.5353 (3)0.51826 (8)0.0309 (4)
H160.11590.47400.54300.037*
C170.25357 (16)0.4478 (3)0.48956 (8)0.0291 (4)
H170.26320.32700.49460.035*
C180.47317 (15)0.5411 (2)0.27066 (7)0.0238 (4)
C190.47697 (17)0.6765 (2)0.22992 (8)0.0296 (4)
H190.54420.75780.23680.036*
C200.38189 (18)0.6928 (3)0.17892 (8)0.0341 (5)
H200.38460.78590.15110.041*
C210.28401 (18)0.5762 (3)0.16814 (9)0.0337 (5)
H210.22040.58710.13280.040*
C220.27925 (18)0.4431 (3)0.20932 (9)0.0361 (5)
H220.21130.36300.20260.043*
C230.37284 (17)0.4255 (3)0.26036 (8)0.0307 (4)
H230.36850.33370.28860.037*
C980.52162 (19)0.1041 (3)0.16055 (9)0.0384 (5)
H98A0.57790.00860.15400.046*
H98B0.44200.09400.13160.046*
H98C0.50370.10030.20300.046*
C990.58476 (17)0.2714 (2)0.14991 (8)0.0319 (4)
H99A0.59360.28050.10580.038*
H99B0.53050.36750.15970.038*
O990.70842 (12)0.28640 (17)0.18736 (6)0.0300 (3)
H0990.7003 (19)0.283 (3)0.2245 (10)0.043 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0427 (3)0.0409 (3)0.0476 (3)0.0088 (2)0.0218 (2)0.0045 (3)
O10.0332 (7)0.0255 (7)0.0255 (6)0.0013 (6)0.0100 (5)0.0066 (6)
N10.0345 (9)0.0246 (9)0.0285 (8)0.0100 (7)0.0114 (7)0.0031 (7)
N20.0312 (8)0.0240 (9)0.0258 (8)0.0042 (7)0.0093 (6)0.0048 (7)
C30.0220 (8)0.0225 (10)0.0215 (8)0.0003 (7)0.0027 (7)0.0011 (7)
C40.0240 (8)0.0210 (10)0.0198 (8)0.0007 (7)0.0035 (7)0.0003 (7)
N30.0480 (11)0.0241 (10)0.0316 (9)0.0073 (9)0.0150 (8)0.0060 (8)
N40.0255 (8)0.0204 (9)0.0268 (8)0.0021 (7)0.0066 (6)0.0033 (7)
C50.0281 (9)0.0234 (10)0.0206 (8)0.0031 (8)0.0043 (7)0.0018 (8)
N50.0280 (8)0.0234 (9)0.0242 (8)0.0001 (7)0.0108 (6)0.0042 (7)
C60.0217 (8)0.0246 (10)0.0186 (8)0.0027 (8)0.0010 (7)0.0007 (8)
C120.0213 (8)0.0254 (10)0.0197 (8)0.0007 (8)0.0041 (7)0.0003 (8)
C130.0262 (9)0.0278 (11)0.0256 (9)0.0042 (8)0.0070 (7)0.0032 (8)
C140.0294 (9)0.0226 (10)0.0316 (9)0.0018 (8)0.0034 (8)0.0015 (8)
C150.0267 (9)0.0307 (12)0.0276 (9)0.0037 (8)0.0068 (7)0.0044 (9)
C160.0304 (10)0.0324 (12)0.0323 (10)0.0012 (9)0.0127 (8)0.0045 (9)
C170.0316 (10)0.0241 (11)0.0335 (10)0.0026 (8)0.0105 (8)0.0045 (8)
C180.0248 (9)0.0238 (10)0.0249 (9)0.0042 (8)0.0109 (7)0.0004 (8)
C190.0335 (10)0.0245 (10)0.0327 (10)0.0004 (8)0.0110 (8)0.0045 (9)
C200.0448 (11)0.0283 (11)0.0312 (10)0.0116 (10)0.0118 (9)0.0098 (9)
C210.0336 (11)0.0360 (12)0.0308 (10)0.0112 (9)0.0028 (8)0.0013 (9)
C220.0298 (10)0.0404 (13)0.0375 (11)0.0038 (9)0.0034 (8)0.0039 (10)
C230.0321 (10)0.0320 (12)0.0285 (10)0.0035 (9)0.0061 (8)0.0090 (9)
C980.0408 (12)0.0338 (12)0.0400 (11)0.0057 (10)0.0045 (9)0.0019 (10)
C990.0388 (11)0.0286 (11)0.0294 (10)0.0023 (9)0.0090 (8)0.0012 (9)
O990.0338 (7)0.0310 (8)0.0281 (7)0.0050 (6)0.0138 (6)0.0002 (6)
Geometric parameters (Å, º) top
Cl—C151.7448 (17)C15—C161.376 (3)
O1—C61.234 (2)C16—C171.384 (3)
N1—C51.344 (2)C16—H160.9500
N1—N21.378 (2)C17—H170.9500
N1—H010.92 (2)C18—C191.385 (2)
N2—C31.316 (2)C18—C231.390 (2)
C3—C41.417 (2)C19—C201.391 (3)
C3—N41.422 (2)C19—H190.9500
C4—C51.394 (2)C20—C211.376 (3)
C4—C61.462 (2)C20—H200.9500
N3—C51.356 (2)C21—C221.380 (3)
N3—H0310.81 (2)C21—H210.9500
N3—H0320.87 (2)C22—C231.383 (2)
N4—C181.431 (2)C22—H220.9500
N4—H040.876 (19)C23—H230.9500
N5—C61.363 (2)C98—C991.501 (3)
N5—C121.406 (2)C98—H98A0.9800
N5—H050.83 (2)C98—H98B0.9800
C12—C171.393 (2)C98—H98C0.9800
C12—C131.396 (2)C99—O991.444 (2)
C13—C141.381 (2)C99—H99A0.9900
C13—H130.9500C99—H99B0.9900
C14—C151.383 (2)O99—H0990.83 (2)
C14—H140.9500
C5—N1—N2112.53 (15)C15—C16—C17120.53 (17)
C5—N1—H01123.9 (12)C15—C16—H16119.7
N2—N1—H01123.5 (12)C17—C16—H16119.7
C3—N2—N1104.24 (14)C16—C17—C12119.77 (18)
N2—C3—C4112.42 (16)C16—C17—H17120.1
N2—C3—N4120.68 (15)C12—C17—H17120.1
C4—C3—N4126.79 (15)C19—C18—C23119.23 (16)
C5—C4—C3104.13 (14)C19—C18—N4120.23 (16)
C5—C4—C6124.33 (15)C23—C18—N4120.54 (16)
C3—C4—C6131.45 (16)C18—C19—C20119.65 (17)
C5—N3—H031117.6 (16)C18—C19—H19120.2
C5—N3—H032117.7 (15)C20—C19—H19120.2
H031—N3—H032116 (2)C21—C20—C19121.02 (18)
C3—N4—C18115.06 (14)C21—C20—H20119.5
C3—N4—H04112.5 (12)C19—C20—H20119.5
C18—N4—H04112.2 (12)C20—C21—C22119.23 (17)
N1—C5—N3122.07 (17)C20—C21—H21120.4
N1—C5—C4106.67 (15)C22—C21—H21120.4
N3—C5—C4131.20 (16)C21—C22—C23120.43 (18)
C6—N5—C12128.81 (15)C21—C22—H22119.8
C6—N5—H05116.0 (14)C23—C22—H22119.8
C12—N5—H05115.1 (14)C22—C23—C18120.41 (17)
O1—C6—N5123.50 (15)C22—C23—H23119.8
O1—C6—C4121.29 (16)C18—C23—H23119.8
N5—C6—C4115.19 (15)C99—C98—H98A109.5
C17—C12—C13118.93 (16)C99—C98—H98B109.5
C17—C12—N5123.83 (17)H98A—C98—H98B109.5
C13—C12—N5117.23 (15)C99—C98—H98C109.5
C14—C13—C12120.98 (16)H98A—C98—H98C109.5
C14—C13—H13119.5H98B—C98—H98C109.5
C12—C13—H13119.5O99—C99—C98112.00 (15)
C13—C14—C15119.24 (17)O99—C99—H99A109.2
C13—C14—H14120.4C98—C99—H99A109.2
C15—C14—H14120.4O99—C99—H99B109.2
C16—C15—C14120.51 (16)C98—C99—H99B109.2
C16—C15—Cl119.34 (14)H99A—C99—H99B107.9
C14—C15—Cl120.15 (15)C99—O99—H099109.0 (14)
C5—N1—N2—C30.60 (19)C6—N5—C12—C13173.07 (16)
N1—N2—C3—C40.05 (18)C17—C12—C13—C141.8 (3)
N1—N2—C3—N4176.45 (14)N5—C12—C13—C14179.13 (15)
N2—C3—C4—C50.47 (19)C12—C13—C14—C150.0 (3)
N4—C3—C4—C5175.67 (16)C13—C14—C15—C161.8 (3)
N2—C3—C4—C6177.17 (16)C13—C14—C15—Cl177.60 (13)
N4—C3—C4—C61.0 (3)C14—C15—C16—C171.8 (3)
N2—C3—N4—C1880.3 (2)Cl—C15—C16—C17177.61 (14)
C4—C3—N4—C1895.58 (19)C15—C16—C17—C120.1 (3)
N2—N1—C5—N3176.73 (16)C13—C12—C17—C161.8 (3)
N2—N1—C5—C40.90 (19)N5—C12—C17—C16179.20 (16)
C3—C4—C5—N10.80 (18)C3—N4—C18—C19145.85 (16)
C6—C4—C5—N1177.80 (15)C3—N4—C18—C2335.1 (2)
C3—C4—C5—N3176.53 (19)C23—C18—C19—C201.1 (3)
C6—C4—C5—N30.5 (3)N4—C18—C19—C20179.82 (16)
C12—N5—C6—O12.6 (3)C18—C19—C20—C210.2 (3)
C12—N5—C6—C4175.73 (15)C19—C20—C21—C221.2 (3)
C5—C4—C6—O11.0 (3)C20—C21—C22—C231.0 (3)
C3—C4—C6—O1177.11 (16)C21—C22—C23—C180.3 (3)
C5—C4—C6—N5177.41 (15)C19—C18—C23—C221.4 (3)
C3—C4—C6—N51.3 (3)N4—C18—C23—C22179.59 (16)
C6—N5—C12—C178.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H032···O10.87 (2)2.41 (2)2.914 (2)117.4 (18)
N5—H05···N40.83 (2)2.26 (2)2.955 (2)142.0 (18)
N1—H01···O99i0.92 (2)1.90 (2)2.801 (2)165.6 (17)
N3—H032···O1ii0.87 (2)2.22 (2)2.950 (2)142 (2)
N4—H04···O99iii0.876 (19)2.30 (2)3.163 (2)170.7 (17)
O99—H099···N20.83 (2)1.96 (2)2.7928 (19)176 (2)
C17—H17···O10.952.282.884 (2)121
C21—H21···O1iv0.952.563.494 (2)167
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1, y, z+1; (iii) x+3/2, y+1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
 

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