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The title compound, C18H17N3O2·CH4O, is a Schiff base compound, which is derived from the condensation of equimolar amounts of 4-amino­antipyrine and 4-hydroxy­benzaldehyde. In the crystal structure, the MeOH molecules are linked to the Schiff base molecules through intermolecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804034324/hg6125sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804034324/hg6125Isup2.hkl
Contains datablock I

CCDC reference: 263674

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.142
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C18H17N3O2·CH4OF(000) = 720
Mr = 339.39Dx = 1.257 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1346 reflections
a = 13.680 (9) Åθ = 3.1–22.0°
b = 6.916 (5) ŵ = 0.09 mm1
c = 19.968 (14) ÅT = 298 K
β = 108.292 (11)°Block, yellow
V = 1794 (2) Å30.43 × 0.24 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3162 independent reflections
Radiation source: fine-focus sealed tube1498 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1216
Tmin = 0.964, Tmax = 0.988k = 88
8910 measured reflectionsl = 2323
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0571P)2 + 0.0741P]
where P = (Fo2 + 2Fc2)/3
3162 reflections(Δ/σ)max < 0.001
231 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.17 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
O10.83700 (14)0.1637 (3)0.11322 (11)0.0592 (6)
O20.19408 (15)0.2549 (3)0.02847 (13)0.0733 (7)
H20.18250.36460.01230.110*
O30.1424 (2)0.3787 (4)0.00736 (15)0.0997 (9)
H3A0.14660.31030.03990.149*
N10.92859 (17)0.1059 (3)0.16723 (12)0.0478 (6)
N20.90488 (17)0.2765 (3)0.19727 (12)0.0493 (6)
N30.65076 (17)0.0904 (3)0.12427 (12)0.0498 (6)
C10.2967 (2)0.2153 (5)0.04429 (16)0.0541 (8)
C20.3654 (2)0.3429 (4)0.03252 (15)0.0564 (8)
H2A0.34340.46370.01310.068*
C30.4675 (2)0.2923 (5)0.04946 (16)0.0577 (9)
H30.51360.38040.04100.069*
C40.5040 (2)0.1152 (4)0.07867 (14)0.0472 (7)
C50.4337 (2)0.0102 (5)0.09091 (16)0.0624 (9)
H50.45560.13040.11090.075*
C60.3312 (2)0.0390 (5)0.07409 (17)0.0686 (10)
H60.28490.04790.08300.082*
C70.6124 (2)0.0666 (4)0.09428 (14)0.0511 (8)
H70.65530.15410.08180.061*
C80.7561 (2)0.1277 (4)0.14170 (14)0.0432 (7)
C90.8375 (2)0.0040 (4)0.13597 (14)0.0461 (7)
C100.8006 (2)0.2903 (4)0.17612 (14)0.0445 (7)
C110.7479 (2)0.4640 (4)0.19167 (16)0.0658 (9)
H11A0.77680.49700.24060.099*
H11B0.67580.43740.18130.099*
H11C0.75690.57010.16320.099*
C120.9752 (2)0.4388 (4)0.20375 (18)0.0706 (10)
H12A0.97350.48110.15760.106*
H12B1.04380.39910.22990.106*
H12C0.95450.54320.22800.106*
C131.0238 (2)0.0107 (4)0.20212 (16)0.0456 (7)
C141.0718 (2)0.0904 (4)0.16144 (16)0.0516 (8)
H141.04430.08970.11250.062*
C151.1604 (2)0.1916 (4)0.19389 (19)0.0612 (9)
H151.19250.26130.16680.073*
C161.2020 (2)0.1905 (5)0.2663 (2)0.0656 (10)
H161.26220.25900.28790.079*
C171.1549 (2)0.0883 (5)0.30680 (17)0.0629 (9)
H171.18360.08660.35560.075*
C181.0652 (2)0.0115 (4)0.27478 (16)0.0542 (8)
H181.03250.07910.30200.065*
C190.0846 (3)0.2843 (6)0.0288 (2)0.0897 (12)
H19A0.09620.34400.07400.135*
H19B0.10490.15090.03510.135*
H19C0.01290.29260.00220.135*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0514 (13)0.0451 (14)0.0776 (16)0.0030 (10)0.0153 (11)0.0178 (11)
O20.0426 (13)0.0788 (18)0.1008 (19)0.0092 (11)0.0258 (12)0.0183 (15)
O30.126 (2)0.0776 (19)0.121 (2)0.0362 (17)0.075 (2)0.0399 (16)
N10.0415 (14)0.0380 (15)0.0590 (16)0.0001 (12)0.0088 (12)0.0045 (12)
N20.0474 (16)0.0340 (15)0.0613 (16)0.0029 (12)0.0097 (12)0.0056 (12)
N30.0423 (15)0.0530 (17)0.0519 (16)0.0022 (13)0.0116 (12)0.0021 (13)
C10.0393 (18)0.065 (2)0.058 (2)0.0035 (17)0.0161 (15)0.0040 (17)
C20.052 (2)0.056 (2)0.063 (2)0.0091 (17)0.0200 (16)0.0153 (17)
C30.0412 (19)0.062 (2)0.070 (2)0.0013 (16)0.0171 (16)0.0122 (18)
C40.0413 (18)0.052 (2)0.0463 (18)0.0013 (15)0.0111 (14)0.0011 (15)
C50.050 (2)0.053 (2)0.085 (2)0.0052 (17)0.0228 (18)0.0133 (18)
C60.048 (2)0.060 (2)0.099 (3)0.0015 (17)0.0256 (18)0.021 (2)
C70.0447 (19)0.056 (2)0.051 (2)0.0013 (16)0.0117 (15)0.0020 (16)
C80.0404 (18)0.0438 (18)0.0447 (18)0.0018 (15)0.0123 (14)0.0008 (14)
C90.0459 (18)0.043 (2)0.0468 (18)0.0055 (16)0.0108 (14)0.0016 (15)
C100.0470 (19)0.0389 (19)0.0479 (19)0.0030 (15)0.0155 (15)0.0045 (14)
C110.066 (2)0.051 (2)0.079 (2)0.0079 (17)0.0215 (18)0.0045 (17)
C120.059 (2)0.043 (2)0.104 (3)0.0138 (16)0.0176 (19)0.0055 (18)
C130.0373 (16)0.0408 (18)0.056 (2)0.0021 (14)0.0103 (15)0.0015 (15)
C140.0471 (19)0.049 (2)0.058 (2)0.0033 (16)0.0154 (16)0.0018 (16)
C150.054 (2)0.053 (2)0.078 (3)0.0049 (17)0.0221 (19)0.0083 (18)
C160.047 (2)0.056 (2)0.086 (3)0.0042 (16)0.010 (2)0.007 (2)
C170.055 (2)0.067 (2)0.062 (2)0.0063 (18)0.0119 (18)0.0103 (19)
C180.0505 (19)0.054 (2)0.058 (2)0.0019 (16)0.0167 (16)0.0002 (16)
C190.069 (3)0.096 (3)0.108 (3)0.007 (2)0.034 (2)0.000 (2)
Geometric parameters (Å, º) top
O1—C91.245 (3)C8—C101.358 (4)
O2—C11.366 (3)C8—C91.436 (4)
O2—H20.8200C10—C111.484 (4)
O3—C191.389 (4)C11—H11A0.9600
O3—H3A0.8200C11—H11B0.9600
N1—C91.397 (3)C11—H11C0.9600
N1—N21.407 (3)C12—H12A0.9600
N1—C131.430 (3)C12—H12B0.9600
N2—C101.358 (3)C12—H12C0.9600
N2—C121.457 (3)C13—C181.382 (4)
N3—C71.271 (3)C13—C141.384 (4)
N3—C81.396 (3)C14—C151.374 (4)
C1—C21.363 (4)C14—H140.9300
C1—C61.373 (4)C15—C161.377 (4)
C2—C31.376 (4)C15—H150.9300
C2—H2A0.9300C16—C171.378 (4)
C3—C41.381 (4)C16—H160.9300
C3—H30.9300C17—C181.378 (4)
C4—C51.372 (4)C17—H170.9300
C4—C71.455 (4)C18—H180.9300
C5—C61.379 (4)C19—H19A0.9600
C5—H50.9300C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C7—H70.9300
C1—O2—H2109.5C8—C10—C11127.3 (3)
C19—O3—H3A109.5C10—C11—H11A109.5
C9—N1—N2108.7 (2)C10—C11—H11B109.5
C9—N1—C13122.3 (2)H11A—C11—H11B109.5
N2—N1—C13118.3 (2)C10—C11—H11C109.5
C10—N2—N1106.7 (2)H11A—C11—H11C109.5
C10—N2—C12124.9 (2)H11B—C11—H11C109.5
N1—N2—C12116.7 (2)N2—C12—H12A109.5
C7—N3—C8121.1 (2)N2—C12—H12B109.5
C2—C1—O2123.0 (3)H12A—C12—H12B109.5
C2—C1—C6119.2 (3)N2—C12—H12C109.5
O2—C1—C6117.8 (3)H12A—C12—H12C109.5
C1—C2—C3119.7 (3)H12B—C12—H12C109.5
C1—C2—H2A120.2C18—C13—C14120.3 (3)
C3—C2—H2A120.2C18—C13—N1121.3 (3)
C2—C3—C4122.3 (3)C14—C13—N1118.3 (3)
C2—C3—H3118.9C15—C14—C13119.5 (3)
C4—C3—H3118.9C15—C14—H14120.3
C5—C4—C3117.1 (3)C13—C14—H14120.3
C5—C4—C7122.7 (3)C14—C15—C16120.4 (3)
C3—C4—C7120.2 (3)C14—C15—H15119.8
C4—C5—C6121.1 (3)C16—C15—H15119.8
C4—C5—H5119.5C15—C16—C17120.3 (3)
C6—C5—H5119.5C15—C16—H16119.9
C1—C6—C5120.6 (3)C17—C16—H16119.9
C1—C6—H6119.7C16—C17—C18119.8 (3)
C5—C6—H6119.7C16—C17—H17120.1
N3—C7—C4122.7 (3)C18—C17—H17120.1
N3—C7—H7118.6C17—C18—C13119.8 (3)
C4—C7—H7118.6C17—C18—H18120.1
C10—C8—N3122.9 (3)C13—C18—H18120.1
C10—C8—C9107.3 (2)O3—C19—H19A109.5
N3—C8—C9129.4 (3)O3—C19—H19B109.5
O1—C9—N1122.3 (3)H19A—C19—H19B109.5
O1—C9—C8132.0 (3)O3—C19—H19C109.5
N1—C9—C8105.6 (2)H19A—C19—H19C109.5
N2—C10—C8111.1 (2)H19B—C19—H19C109.5
N2—C10—C11121.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.821.862.668 (4)166
O3—H3A···O1ii0.821.852.671 (3)177
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z.
 

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