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We report the crystal structure and crystallization conditions of a first hydrated form of metacetamol (a hemihydrate), C8H9NO2·0.5H2O. It crystallizes from metacetamol-saturated 1:1 (v/v) water–ethanol solutions in a monoclinic structure (space group P21/n) and contains eight metacetamol and four water mol­ecules per unit cell. The conformations of the mol­ecules are the same as in polymorph II of metacetamol, which ensures the formation of hydrogen-bonded dimers and R22(16) ring motifs in its crystal structure similar to those in polymorph II. Unlike in form II, however, these dimers in the hemihydrate are connected through water mol­ecules into infinite hydrogen-bonded mol­ecular chains. Different chains are linked to each other by metacetamol–water and metacetamol–metacetamol hydrogen bonds, the latter type being also present in polymorph I. The overall noncovalent network of the hemihydrate is well developed and several types of hydrogen bonds are responsible for its formation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619012981/cu3154sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012981/cu3154Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619012981/cu3154Isup3.cml
Supplementary material

CCDC reference: 1954774

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N-(3-Hydroxyphenyl)acetamide hemihydrate top
Crystal data top
2C8H9NO2·H2OF(000) = 680
Mr = 320.34Dx = 1.262 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.7626 (4) ÅCell parameters from 4399 reflections
b = 6.92827 (14) Åθ = 1.7–24.2°
c = 19.7011 (4) ŵ = 0.09 mm1
β = 104.619 (3)°T = 295 K
V = 1685.62 (8) Å3Block, colourless
Z = 40.3 × 0.2 × 0.1 mm
Data collection top
Rigaku Xcalibur Ruby Gemini ultra
diffractometer
3209 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source2204 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 10.3457 pixels mm-1θmax = 25.7°, θmin = 1.7°
ω scansh = 1515
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 88
Tmin = 0.968, Tmax = 1.000l = 2424
20645 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0471P)2 + 0.2986P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3209 reflectionsΔρmax = 0.15 e Å3
274 parametersΔρmin = 0.15 e Å3
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O110.13102 (15)0.0755 (2)0.52095 (8)0.0861 (6)
H110.095 (2)0.167 (4)0.4888 (14)0.110 (9)*
O210.03939 (16)0.6558 (2)0.57158 (7)0.0899 (6)
N110.00908 (14)0.5130 (2)0.67710 (8)0.0543 (5)
H11A0.0053 (15)0.523 (3)0.7214 (12)0.064 (6)*
C110.06446 (15)0.3468 (3)0.66289 (9)0.0470 (5)
C210.06817 (17)0.2941 (3)0.59582 (10)0.0543 (5)
H210.0323 (16)0.366 (3)0.5570 (11)0.068 (6)*
C310.12470 (17)0.1302 (3)0.58617 (10)0.0577 (5)
C410.17654 (19)0.0186 (3)0.64273 (12)0.0657 (6)
H410.2146 (18)0.092 (3)0.6337 (11)0.081 (7)*
C510.17180 (18)0.0722 (4)0.70877 (12)0.0657 (6)
H510.2070 (17)0.003 (3)0.7490 (12)0.081 (7)*
C610.11587 (16)0.2345 (3)0.71957 (10)0.0563 (5)
H610.1118 (14)0.274 (3)0.7663 (11)0.058 (5)*
C710.03749 (17)0.6556 (3)0.63367 (10)0.0556 (5)
C810.08655 (19)0.8159 (3)0.66606 (11)0.0664 (6)
H81A0.05000.93460.66170.100*
H81B0.07930.78820.71480.100*
H81C0.16190.82780.64250.100*
O120.52609 (13)0.9883 (2)0.67514 (7)0.0685 (5)
O220.56527 (14)0.8283 (2)0.44372 (7)0.0729 (5)
N120.63940 (14)0.5709 (2)0.50799 (8)0.0521 (4)
C120.63225 (14)0.6233 (2)0.57617 (9)0.0454 (4)
C220.58092 (16)0.7885 (3)0.59045 (9)0.0471 (5)
C320.57719 (15)0.8275 (3)0.65887 (9)0.0474 (5)
C420.62505 (16)0.7049 (3)0.71278 (10)0.0525 (5)
C520.67631 (18)0.5425 (3)0.69765 (11)0.0604 (6)
C620.67959 (17)0.4988 (3)0.63012 (11)0.0572 (5)
C720.60799 (16)0.6689 (3)0.44774 (10)0.0499 (5)
C820.62801 (18)0.5726 (3)0.38414 (10)0.0636 (6)
H82A0.56000.54470.35150.095*
H82B0.66710.45450.39770.095*
H82C0.66980.65670.36240.095*
O1WA0.7127 (3)0.1769 (4)0.50402 (18)0.0986 (12)0.736 (6)
H1WA0.66580.08600.49660.148*0.736 (6)
H1WB0.77150.12420.49930.148*0.736 (6)
O1WB0.7969 (8)0.2862 (14)0.5064 (6)0.128 (5)0.264 (6)
H1WC0.86410.31330.51070.192*0.264 (6)
H1WD0.78650.18360.48190.192*0.264 (6)
H420.6227 (15)0.738 (3)0.7588 (11)0.063 (6)*
H220.5436 (14)0.874 (3)0.5526 (10)0.054 (5)*
H620.7149 (17)0.385 (3)0.6185 (11)0.075 (7)*
H520.7091 (16)0.457 (3)0.7332 (11)0.072 (6)*
H12A0.6737 (18)0.458 (3)0.5056 (12)0.087 (8)*
H120.494 (2)1.054 (4)0.6328 (14)0.098 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.1278 (15)0.0825 (11)0.0536 (9)0.0563 (11)0.0333 (9)0.0077 (8)
O210.1552 (16)0.0758 (11)0.0434 (9)0.0521 (10)0.0339 (9)0.0078 (7)
N110.0766 (12)0.0542 (10)0.0353 (9)0.0008 (8)0.0199 (8)0.0050 (8)
C110.0527 (11)0.0477 (11)0.0402 (10)0.0037 (9)0.0111 (8)0.0011 (8)
C210.0676 (14)0.0547 (12)0.0401 (11)0.0110 (10)0.0125 (10)0.0039 (9)
C310.0691 (13)0.0607 (13)0.0465 (11)0.0150 (11)0.0204 (10)0.0027 (10)
C410.0713 (15)0.0655 (14)0.0627 (14)0.0212 (12)0.0212 (11)0.0129 (12)
C510.0651 (14)0.0771 (16)0.0523 (13)0.0143 (12)0.0101 (11)0.0174 (12)
C610.0599 (13)0.0684 (14)0.0396 (11)0.0052 (11)0.0105 (10)0.0030 (10)
C710.0741 (14)0.0519 (12)0.0435 (11)0.0015 (10)0.0197 (10)0.0065 (9)
C810.0843 (15)0.0552 (13)0.0657 (14)0.0019 (11)0.0300 (12)0.0159 (10)
O120.1140 (13)0.0569 (9)0.0377 (8)0.0214 (8)0.0248 (8)0.0040 (7)
O220.1237 (13)0.0544 (9)0.0421 (8)0.0323 (9)0.0238 (8)0.0049 (6)
N120.0652 (11)0.0423 (9)0.0492 (10)0.0113 (8)0.0151 (8)0.0006 (8)
C120.0525 (11)0.0402 (10)0.0430 (10)0.0008 (8)0.0113 (8)0.0022 (8)
C220.0635 (13)0.0408 (10)0.0355 (10)0.0051 (9)0.0097 (9)0.0050 (8)
C320.0593 (12)0.0427 (10)0.0399 (10)0.0008 (9)0.0121 (9)0.0027 (8)
C420.0567 (12)0.0621 (13)0.0371 (11)0.0042 (10)0.0088 (9)0.0101 (9)
C520.0611 (13)0.0653 (14)0.0539 (13)0.0110 (11)0.0130 (10)0.0257 (11)
C620.0609 (13)0.0512 (12)0.0606 (13)0.0134 (10)0.0174 (10)0.0142 (10)
C720.0611 (12)0.0443 (11)0.0457 (11)0.0027 (9)0.0160 (9)0.0040 (9)
C820.0814 (15)0.0609 (13)0.0533 (12)0.0013 (11)0.0257 (11)0.0134 (10)
O1WA0.093 (2)0.0519 (15)0.160 (3)0.0120 (14)0.050 (2)0.0140 (15)
O1WB0.095 (7)0.078 (7)0.205 (10)0.029 (6)0.024 (6)0.034 (6)
Geometric parameters (Å, º) top
O11—H110.93 (3)O22—C721.225 (2)
O11—C311.361 (2)N12—C121.416 (2)
O21—C711.217 (2)N12—C721.338 (2)
N11—H11A0.89 (2)N12—H12A0.91 (2)
N11—C111.416 (2)C12—C221.383 (2)
N11—C711.343 (2)C12—C621.384 (3)
C11—C211.383 (3)C22—C321.387 (2)
C11—C611.383 (3)C22—H220.978 (18)
C21—H210.93 (2)C32—C421.377 (2)
C21—C311.384 (3)C42—C521.371 (3)
C31—C411.380 (3)C42—H420.94 (2)
C41—H410.95 (2)C52—C621.375 (3)
C41—C511.369 (3)C52—H520.93 (2)
C51—H510.96 (2)C62—H620.96 (2)
C51—C611.377 (3)C72—C821.498 (2)
C61—H610.98 (2)C82—H82A0.9600
C71—C811.495 (3)C82—H82B0.9600
C81—H81A0.9600C82—H82C0.9600
C81—H81B0.9600O1WA—H1WA0.8558
C81—H81C0.9600O1WA—H1WB0.8604
O12—C321.369 (2)O1WB—H1WC0.8613
O12—H120.95 (3)O1WB—H1WD0.8502
C31—O11—H11108.5 (16)C12—N12—H12A114.8 (15)
C11—N11—H11A114.2 (13)C72—N12—C12129.36 (16)
C71—N11—H11A116.4 (13)C72—N12—H12A115.8 (15)
C71—N11—C11129.42 (16)C22—C12—N12123.55 (16)
C21—C11—N11122.86 (17)C22—C12—C62119.83 (17)
C61—C11—N11117.16 (17)C62—C12—N12116.63 (17)
C61—C11—C21119.97 (19)C12—C22—C32119.55 (17)
C11—C21—H21121.1 (12)C12—C22—H22120.7 (10)
C11—C21—C31119.49 (19)C32—C22—H22119.6 (10)
C31—C21—H21119.4 (12)O12—C32—C22121.40 (16)
O11—C31—C21121.00 (18)O12—C32—C42117.80 (17)
O11—C31—C41118.40 (18)C42—C32—C22120.80 (18)
C41—C31—C21120.60 (19)C32—C42—H42118.5 (12)
C31—C41—H41117.8 (14)C52—C42—C32118.79 (19)
C51—C41—C31119.2 (2)C52—C42—H42122.7 (12)
C51—C41—H41123.0 (13)C42—C52—C62121.59 (19)
C41—C51—H51120.8 (13)C42—C52—H52120.4 (12)
C41—C51—C61121.1 (2)C62—C52—H52118.0 (12)
C61—C51—H51118.0 (13)C12—C62—H62117.9 (13)
C11—C61—H61118.5 (11)C52—C62—C12119.43 (19)
C51—C61—C11119.55 (19)C52—C62—H62122.7 (12)
C51—C61—H61122.0 (11)O22—C72—N12122.94 (17)
O21—C71—N11122.31 (18)O22—C72—C82120.98 (18)
O21—C71—C81121.57 (19)N12—C72—C82116.08 (17)
N11—C71—C81116.11 (17)C72—C82—H82A109.5
C71—C81—H81A109.5C72—C82—H82B109.5
C71—C81—H81B109.5C72—C82—H82C109.5
C71—C81—H81C109.5H82A—C82—H82B109.5
H81A—C81—H81B109.5H82A—C82—H82C109.5
H81A—C81—H81C109.5H82B—C82—H82C109.5
H81B—C81—H81C109.5H1WA—O1WA—H1WB105.1
C32—O12—H12107.9 (15)H1WC—O1WB—H1WD104.3
O11—C31—C41—C51179.5 (2)O12—C32—C42—C52179.75 (18)
N11—C11—C21—C31179.51 (18)N12—C12—C22—C32179.50 (17)
N11—C11—C61—C51179.39 (19)N12—C12—C62—C52179.39 (18)
C11—N11—C71—O211.7 (3)C12—N12—C72—O220.4 (3)
C11—N11—C71—C81177.90 (18)C12—N12—C72—C82179.53 (18)
C11—C21—C31—O11179.24 (19)C12—C22—C32—O12179.24 (17)
C11—C21—C31—C410.5 (3)C12—C22—C32—C420.7 (3)
C21—C11—C61—C510.9 (3)C22—C12—C62—C520.9 (3)
C21—C31—C41—C510.2 (3)C22—C32—C42—C520.2 (3)
C31—C41—C51—C610.3 (4)C32—C42—C52—C620.9 (3)
C41—C51—C61—C110.7 (3)C42—C52—C62—C121.5 (3)
C61—C11—C21—C310.8 (3)C62—C12—C22—C320.1 (3)
C71—N11—C11—C217.8 (3)C72—N12—C12—C225.4 (3)
C71—N11—C11—C61172.50 (19)C72—N12—C12—C62174.95 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O11—H11···O21i0.93 (3)1.73 (3)2.660 (2)175 (3)
N11—H11A···O12ii0.89 (2)2.19 (2)3.060 (2)167.1 (18)
O1WA—H1WA···O22iii0.862.293.108 (4)160
O1WA—H1WB···O11iv0.861.972.788 (3)159
O1WB—H1WD···O11iv0.852.092.769 (8)137
N12—H12A···O1WA0.91 (2)2.01 (2)2.893 (3)165 (2)
N12—H12A···O1WB0.91 (2)1.97 (2)2.822 (7)157 (2)
O12—H12···O22v0.95 (3)1.71 (3)2.6605 (19)179 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1/2, y1/2, z+3/2; (iii) x, y1, z; (iv) x+1, y, z+1; (v) x+1, y+2, z+1.
 

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