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The crystal structure of the title compound, C7H8N2O4·H2O, has been determined in the monoclinic system with the space group C2/c. It is an intermediate compound for synthesizing oligomeric carbox­amides, which can bind to DNA by lodging in the minor groove. The mol­ecules are linked into two-dimensional sheets by O—H...N and O—H...O hydrogen-bonding interactions. The sheets form a three-dimensional network via weak intermolecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026485/hg6007sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026485/hg6007Isup2.hkl
Contains datablock I

CCDC reference: 227907

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.052
  • wR factor = 0.142
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
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 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 0 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 (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996) and SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Methyl 5-carboxyl-1-methylpyrazole-3-carboxylate monohydrate top
Crystal data top
C7H8N2O4·H2OF(000) = 848
Mr = 202.17Dx = 1.490 Mg m3
Monoclinic, C2/cMelting point: 403 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 13.641 (3) ÅCell parameters from 4940 reflections
b = 7.3197 (15) Åθ = 2.3–26.6°
c = 18.660 (4) ŵ = 0.13 mm1
β = 104.62 (3)°T = 183 K
V = 1802.8 (6) Å3Block, colorless
Z = 80.30 × 0.30 × 0.20 mm
Data collection top
CCD area-detector
diffractometer
1590 independent reflections
Radiation source: fine-focus sealed tube1337 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 100x100 microns pixels mm-1θmax = 25.0°, θmin = 2.3°
Ω scansh = 1216
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 87
Tmin = 0.963, Tmax = 0.975l = 2222
3564 measured reflections
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.078P)2 + 0.9903P]
where P = (Fo2 + 2Fc2)/3
1590 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.30 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
N10.80470 (14)0.0287 (3)0.60690 (10)0.0250 (5)
N20.75120 (14)0.0031 (2)0.53748 (10)0.0256 (5)
O10.88962 (13)0.0122 (3)0.76616 (9)0.0436 (5)
O20.73907 (13)0.0848 (3)0.77563 (9)0.0434 (5)
H2A0.76810.08750.82100.052*
O30.51878 (13)0.2455 (3)0.48181 (9)0.0452 (5)
O40.61462 (12)0.1093 (2)0.41605 (8)0.0314 (5)
O50.82447 (12)0.1050 (3)0.91338 (9)0.0407 (5)
H5B0.80230.06730.94910.049*
H5A0.89100.14480.93650.049*
C10.80404 (17)0.0343 (3)0.73827 (13)0.0277 (6)
C20.76010 (17)0.0459 (3)0.65757 (12)0.0255 (5)
C30.67392 (16)0.1332 (3)0.61847 (12)0.0259 (5)
H3A0.62630.19920.63780.031*
C40.67168 (16)0.1036 (3)0.54432 (12)0.0244 (5)
C50.59338 (17)0.1617 (3)0.47854 (12)0.0271 (6)
C60.53964 (18)0.1490 (4)0.34767 (13)0.0377 (7)
H6A0.56370.10410.30560.057*
H6B0.52880.28130.34300.057*
H6C0.47570.08850.34810.057*
C70.89411 (18)0.1453 (3)0.61803 (13)0.0326 (6)
H7A0.90630.17620.56990.049*
H7B0.88300.25760.64350.049*
H7C0.95310.08040.64820.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0222 (10)0.0307 (11)0.0215 (10)0.0023 (8)0.0040 (8)0.0002 (8)
N20.0246 (10)0.0303 (11)0.0219 (10)0.0002 (8)0.0057 (8)0.0006 (8)
O10.0267 (10)0.0744 (15)0.0276 (10)0.0058 (9)0.0032 (8)0.0010 (9)
O20.0362 (10)0.0710 (14)0.0233 (10)0.0154 (9)0.0080 (8)0.0006 (8)
O30.0327 (10)0.0657 (13)0.0359 (11)0.0210 (10)0.0065 (8)0.0002 (9)
O40.0319 (9)0.0387 (10)0.0216 (9)0.0047 (7)0.0029 (7)0.0006 (7)
O50.0352 (10)0.0620 (13)0.0249 (10)0.0129 (9)0.0077 (8)0.0012 (8)
C10.0267 (13)0.0317 (13)0.0255 (13)0.0026 (10)0.0078 (10)0.0008 (10)
C20.0258 (12)0.0276 (12)0.0249 (12)0.0037 (10)0.0101 (10)0.0008 (10)
C30.0224 (12)0.0302 (13)0.0262 (13)0.0030 (10)0.0080 (9)0.0001 (10)
C40.0223 (12)0.0256 (12)0.0253 (12)0.0011 (9)0.0060 (9)0.0001 (9)
C50.0261 (12)0.0283 (13)0.0271 (13)0.0013 (10)0.0072 (10)0.0003 (10)
C60.0365 (15)0.0450 (16)0.0267 (14)0.0023 (12)0.0009 (11)0.0049 (11)
C70.0294 (13)0.0385 (14)0.0292 (13)0.0093 (11)0.0062 (10)0.0027 (11)
Geometric parameters (Å, º) top
N1—N21.337 (3)O4—C61.449 (3)
N1—C21.361 (3)C3—H3A0.9500
N1—C71.460 (3)O2—H2A0.8400
N2—C41.343 (3)O5—H5B0.8447
O1—C11.201 (3)O5—H5A0.9467
O2—C11.311 (3)C6—H6A0.9800
C1—C21.476 (3)C6—H6B0.9800
C2—C31.375 (3)C6—H6C0.9800
C3—C41.393 (3)C7—H7A0.9800
C4—C51.472 (3)C7—H7B0.9800
O3—C51.203 (3)C7—H7C0.9800
O4—C51.327 (3)
N2—N1—C2111.88 (18)N2—C4—C5120.8 (2)
N2—N1—C7118.15 (18)C3—C4—C5127.8 (2)
C2—N1—C7129.77 (19)O3—C5—O4124.5 (2)
N1—N2—C4105.05 (18)O3—C5—C4123.4 (2)
C1—O2—H2A109.5O4—C5—C4112.1 (2)
C5—O4—C6116.98 (19)O4—C6—H6A109.5
H5B—O5—H5A103.5O4—C6—H6B109.5
O1—C1—O2124.2 (2)H6A—C6—H6B109.5
O1—C1—C2123.9 (2)O4—C6—H6C109.5
O2—C1—C2111.8 (2)H6A—C6—H6C109.5
N1—C2—C3106.86 (19)H6B—C6—H6C109.5
N1—C2—C1123.2 (2)N1—C7—H7A109.5
C3—C2—C1129.9 (2)N1—C7—H7B109.5
C2—C3—C4104.9 (2)H7A—C7—H7B109.5
C2—C3—H3A127.6N1—C7—H7C109.5
C4—C3—H3A127.6H7A—C7—H7C109.5
N2—C4—C3111.3 (2)H7B—C7—H7C109.5
C2—N1—N2—C41.2 (2)C1—C2—C3—C4178.0 (2)
C7—N1—N2—C4176.54 (19)N1—N2—C4—C30.9 (2)
N2—N1—C2—C31.0 (3)N1—N2—C4—C5178.39 (19)
C7—N1—C2—C3175.7 (2)C2—C3—C4—N20.3 (3)
N2—N1—C2—C1178.8 (2)C2—C3—C4—C5177.6 (2)
C7—N1—C2—C16.5 (4)C6—O4—C5—O33.2 (3)
O1—C1—C2—N113.5 (4)C6—O4—C5—C4176.25 (19)
O2—C1—C2—N1167.8 (2)N2—C4—C5—O3177.0 (2)
O1—C1—C2—C3163.7 (3)C3—C4—C5—O30.0 (4)
O2—C1—C2—C314.9 (4)N2—C4—C5—O42.5 (3)
N1—C2—C3—C40.4 (3)C3—C4—C5—O4179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5B···N2i0.842.012.856 (2)176
O5—H5A···O3ii0.951.912.854 (2)173
C7—H7A···O3iii0.982.583.489 (3)154
C7—H7C···O1iv0.982.383.332 (3)163
O2—H2A···O50.841.712.544 (2)177
Symmetry codes: (i) x, y, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y1/2, z; (iv) x+2, y, z+3/2.
 

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