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The title compound, C8H8N2O4, differs in its degree of planarity from the 3-nitro isomer and also in its hydrogen-bonding pattern. Its NH group forms an intra­molecular hydrogen bond to a nitro oxygen atom, and its OH group forms an inter­molecular hydrogen bond to an amide oxygen atom, generating [10\overline{1}] chains in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314622002012/hb4400sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314622002012/hb4400Isup3.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314622002012/hb4400Isup3.cml
Supplementary material

CCDC reference: 2153454

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.095
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O3 ..O3 . 2.74 Ang. 1-x,1-y,1-z = 5_666 Check
Alert level C PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 10 Report
Alert level G PLAT432_ALERT_2_G Short Inter X...Y Contact C4 ..C6 . 3.20 Ang. 3/2-x,1/2-y,1-z = 7_656 Check PLAT432_ALERT_2_G Short Inter X...Y Contact C6 ..C6 . 3.16 Ang. 1-x,y,1/2-z = 2_655 Check PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 17 Note PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 1 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2020); ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

N-(4-Hydroxy-2-nitrophenyl)acetamide top
Crystal data top
C8H8N2O4F(000) = 816
Mr = 196.16Dx = 1.569 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54184 Å
a = 9.6643 (3) ÅCell parameters from 5235 reflections
b = 18.5534 (5) Åθ = 4.8–69.3°
c = 9.3072 (2) ŵ = 1.10 mm1
β = 95.5075 (14)°T = 90 K
V = 1661.13 (8) Å3Lath, yellow
Z = 80.21 × 0.07 × 0.02 mm
Data collection top
Bruker Kappa APEXII DUO CCD
diffractometer
1543 independent reflections
Radiation source: IµS microfocus1486 reflections with I > 2σ(I)
QUAZAR multilayer optics monochromatorRint = 0.028
φ and ω scansθmax = 69.3°, θmin = 4.8°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 117
Tmin = 0.872, Tmax = 0.978k = 2220
6856 measured reflectionsl = 1110
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0487P)2 + 1.5639P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max < 0.001
1543 reflectionsΔρmax = 0.29 e Å3
134 parametersΔρmin = 0.23 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were located in difference maps and those on C were thereafter treated as riding in geometrically idealized positions with C—H distances 0.95 Å for phenyl and 0.98 Å for methyl. The coordinates of the N—H and O—H hydrogen atoms were refined. Uiso(H) values were assigned as 1.2Ueq for the attached atom (1.5 for OH and methyl).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.49965 (11)0.11112 (5)0.49610 (11)0.0180 (2)
H1O0.435 (2)0.1126 (10)0.551 (2)0.027*
O20.36347 (11)0.35035 (5)0.64809 (11)0.0240 (3)
O30.47807 (11)0.43019 (5)0.53985 (12)0.0239 (3)
O40.79942 (10)0.37109 (5)0.17917 (10)0.0208 (3)
N10.44852 (12)0.36642 (6)0.56392 (12)0.0163 (3)
N20.65588 (12)0.39184 (6)0.35604 (12)0.0149 (3)
H2N0.6134 (17)0.4246 (10)0.4050 (18)0.018*
C10.53400 (14)0.18008 (7)0.46502 (14)0.0143 (3)
C20.47727 (13)0.23927 (7)0.52723 (13)0.0146 (3)
H20.41130.23270.59550.018*
C30.51647 (13)0.30877 (7)0.49012 (13)0.0138 (3)
C40.61410 (13)0.32179 (7)0.39015 (13)0.0137 (3)
C50.66952 (13)0.26010 (7)0.32904 (13)0.0140 (3)
H50.73560.26590.26060.017*
C60.63082 (13)0.19119 (7)0.36548 (13)0.0143 (3)
H60.67080.15090.32200.017*
C70.74622 (13)0.41291 (7)0.25993 (14)0.0152 (3)
C80.77664 (15)0.49227 (7)0.26014 (16)0.0211 (3)
H8A0.84740.50360.33950.032*
H8B0.69140.51920.27290.032*
H8C0.81090.50580.16810.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0214 (5)0.0120 (5)0.0220 (5)0.0007 (4)0.0096 (4)0.0002 (4)
O20.0279 (6)0.0189 (5)0.0287 (6)0.0003 (4)0.0202 (4)0.0005 (4)
O30.0298 (6)0.0121 (5)0.0327 (6)0.0014 (4)0.0180 (5)0.0002 (4)
O40.0256 (5)0.0158 (5)0.0234 (5)0.0000 (4)0.0141 (4)0.0013 (4)
N10.0175 (6)0.0143 (6)0.0182 (6)0.0003 (4)0.0073 (4)0.0003 (4)
N20.0148 (6)0.0129 (5)0.0179 (6)0.0009 (4)0.0061 (4)0.0006 (4)
C10.0142 (6)0.0132 (6)0.0155 (6)0.0010 (5)0.0005 (5)0.0010 (5)
C20.0143 (6)0.0159 (7)0.0143 (6)0.0002 (5)0.0041 (5)0.0001 (5)
C30.0140 (6)0.0141 (7)0.0136 (6)0.0017 (5)0.0026 (5)0.0019 (5)
C40.0124 (6)0.0153 (6)0.0133 (6)0.0002 (5)0.0004 (5)0.0004 (5)
C50.0122 (6)0.0165 (7)0.0138 (6)0.0003 (5)0.0031 (5)0.0003 (5)
C60.0134 (6)0.0152 (6)0.0145 (6)0.0016 (5)0.0025 (5)0.0013 (5)
C70.0142 (6)0.0143 (6)0.0173 (6)0.0006 (5)0.0028 (5)0.0010 (5)
C80.0245 (7)0.0142 (7)0.0266 (7)0.0006 (5)0.0125 (6)0.0002 (5)
Geometric parameters (Å, º) top
O1—C11.3599 (16)C2—C31.3966 (18)
O1—H1O0.84 (2)C2—H20.9500
O2—N11.2255 (15)C3—C41.4081 (18)
O3—N11.2424 (15)C4—C51.4067 (18)
O4—C71.2270 (17)C5—C61.3835 (18)
N1—C31.4608 (17)C5—H50.9500
N2—C71.3657 (18)C6—H60.9500
N2—C41.4063 (17)C7—C81.5014 (18)
N2—H2N0.883 (19)C8—H8A0.9800
C1—C21.3795 (18)C8—H8B0.9800
C1—C61.3938 (19)C8—H8C0.9800
C1—O1—H1O108.0 (12)N2—C4—C3122.20 (12)
O2—N1—O3121.80 (11)C5—C4—C3115.65 (12)
O2—N1—C3118.79 (11)C6—C5—C4122.03 (12)
O3—N1—C3119.41 (11)C6—C5—H5119.0
C7—N2—C4128.89 (12)C4—C5—H5119.0
C7—N2—H2N119.9 (11)C5—C6—C1120.94 (12)
C4—N2—H2N111.2 (11)C5—C6—H6119.5
O1—C1—C2123.01 (12)C1—C6—H6119.5
O1—C1—C6118.27 (12)O4—C7—N2123.52 (12)
C2—C1—C6118.72 (12)O4—C7—C8121.83 (12)
C1—C2—C3120.20 (12)N2—C7—C8114.66 (11)
C1—C2—H2119.9C7—C8—H8A109.5
C3—C2—H2119.9C7—C8—H8B109.5
C2—C3—C4122.46 (12)H8A—C8—H8B109.5
C2—C3—N1114.51 (11)C7—C8—H8C109.5
C4—C3—N1123.02 (12)H8A—C8—H8C109.5
N2—C4—C5122.14 (12)H8B—C8—H8C109.5
O1—C1—C2—C3179.68 (11)N1—C3—C4—N21.39 (19)
C6—C1—C2—C30.19 (19)C2—C3—C4—C50.31 (18)
C1—C2—C3—C40.29 (19)N1—C3—C4—C5180.00 (11)
C1—C2—C3—N1180.00 (11)N2—C4—C5—C6178.36 (11)
O2—N1—C3—C21.17 (17)C3—C4—C5—C60.25 (18)
O3—N1—C3—C2178.91 (11)C4—C5—C6—C10.18 (19)
O2—N1—C3—C4179.12 (12)O1—C1—C6—C5179.74 (11)
O3—N1—C3—C40.79 (19)C2—C1—C6—C50.13 (19)
C7—N2—C4—C53.1 (2)C4—N2—C7—O45.1 (2)
C7—N2—C4—C3178.38 (12)C4—N2—C7—C8174.86 (12)
C2—C3—C4—N2178.30 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O4i0.84 (2)1.88 (2)2.7183 (14)172.0 (18)
N2—H2N···O30.883 (19)1.901 (17)2.6363 (15)139.6 (15)
Symmetry code: (i) x1/2, y+1/2, z+1/2.
 

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