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2-[(4-Acetyl­phen­yl)carbamo­yl]phenyl acetate, a derivative of aspirin, has been structurally characterized revealing a structure based on inter­molecular N—H...O hydrogen bonds and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023008526/dj2060sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023008526/dj2060Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023008526/dj2060Isup3.cml
Supplementary material

docx

Microsoft Word (DOCX) file https://doi.org/10.1107/S2056989023008526/dj2060sup4.docx
Supplementary material

CCDC reference: 2087303

Computing details top

Data collection: CrysAlis PRO 1.171.40.53 (Rigaku OD, 2019); cell refinement: CrysAlis PRO 1.171.40.53 (Rigaku OD, 2019); data reduction: CrysAlis PRO 1.171.40.53 (Rigaku OD, 2019); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2019/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020).

2-[(4-Acetylphenyl)carbamoyl]phenyl acetate top
Crystal data top
C17H15NO4F(000) = 624
Mr = 297.30Dx = 1.318 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 11.6286 (5) ÅCell parameters from 5304 reflections
b = 8.6913 (4) Åθ = 4.1–76.2°
c = 15.8180 (7) ŵ = 0.78 mm1
β = 110.380 (5)°T = 296 K
V = 1498.62 (12) Å3Needle, yellow
Z = 40.35 × 0.14 × 0.13 mm
Data collection top
Agilent SuperNova, Dual, Cu at home/near, Atlas
diffractometer
2612 reflections with I > 2σ(I)
ω scansRint = 0.027
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2019)
θmax = 76.9°, θmin = 4.1°
Tmin = 0.390, Tmax = 1.000h = 1414
17065 measured reflectionsk = 1010
3141 independent reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0761P)2 + 0.1892P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
3141 reflectionsΔρmax = 0.17 e Å3
201 parametersΔρmin = 0.16 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*/Ueq
C10.5388 (2)0.1466 (3)0.63141 (13)0.0868 (6)
H1A0.5875980.1052440.6890020.130*
H1B0.4984870.0642120.5917390.130*
H1C0.4783720.2153980.6388330.130*
C20.61923 (14)0.23211 (19)0.59205 (9)0.0576 (4)
C30.56774 (12)0.29253 (17)0.49855 (9)0.0505 (3)
C40.64622 (13)0.36063 (19)0.46058 (10)0.0587 (4)
H40.7289420.3706910.4950500.070*
C50.60455 (13)0.41363 (19)0.37314 (10)0.0589 (4)
H50.6589150.4573510.3486380.071*
C60.48068 (12)0.40141 (16)0.32165 (8)0.0490 (3)
C70.40109 (13)0.3340 (2)0.35836 (10)0.0624 (4)
H70.3182080.3253270.3240400.075*
C80.44443 (13)0.2795 (2)0.44606 (10)0.0619 (4)
H80.3903860.2336330.4700960.074*
C90.48064 (13)0.56038 (17)0.19145 (9)0.0539 (3)
C100.41025 (12)0.58347 (17)0.09278 (9)0.0512 (3)
C110.38681 (13)0.73080 (17)0.05690 (10)0.0532 (3)
C120.32771 (14)0.7548 (2)0.03390 (11)0.0629 (4)
H120.3117680.8544020.0564850.075*
C130.29218 (15)0.6303 (2)0.09134 (10)0.0668 (4)
H130.2529950.6461570.1528720.080*
C140.31454 (15)0.4827 (2)0.05786 (10)0.0634 (4)
H140.2910760.3988670.0966450.076*
C150.37213 (14)0.45989 (19)0.03382 (10)0.0574 (4)
H150.3855670.3601300.0563970.069*
C160.52387 (15)0.93013 (18)0.12475 (11)0.0606 (4)
C170.5436 (2)1.0612 (2)0.18968 (14)0.0858 (6)
H17A0.5594861.0216280.2493460.129*
H17B0.4716101.1246740.1725430.129*
H17C0.6124951.1212220.1888000.129*
N10.43273 (11)0.45087 (15)0.23117 (7)0.0547 (3)
H10.3661610.4072570.1974900.066*
O10.72755 (11)0.25066 (17)0.63648 (8)0.0776 (4)
O20.57285 (12)0.63430 (15)0.23103 (8)0.0745 (4)
O30.41633 (10)0.85821 (13)0.11491 (8)0.0629 (3)
O40.58982 (12)0.89231 (15)0.08529 (9)0.0739 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0814 (12)0.1205 (18)0.0571 (9)0.0023 (11)0.0223 (9)0.0268 (10)
C20.0559 (8)0.0687 (9)0.0445 (7)0.0146 (6)0.0127 (6)0.0053 (6)
C30.0473 (7)0.0592 (8)0.0412 (6)0.0072 (5)0.0108 (5)0.0026 (5)
C40.0424 (7)0.0737 (10)0.0497 (7)0.0019 (6)0.0030 (5)0.0093 (6)
C50.0461 (7)0.0745 (10)0.0496 (7)0.0079 (6)0.0087 (6)0.0102 (6)
C60.0478 (7)0.0533 (7)0.0391 (6)0.0021 (5)0.0067 (5)0.0010 (5)
C70.0422 (7)0.0892 (11)0.0470 (7)0.0061 (7)0.0045 (5)0.0094 (7)
C80.0470 (7)0.0872 (11)0.0497 (7)0.0017 (7)0.0146 (6)0.0110 (7)
C90.0555 (7)0.0560 (8)0.0444 (7)0.0038 (6)0.0101 (6)0.0016 (5)
C100.0477 (7)0.0579 (8)0.0452 (7)0.0002 (5)0.0127 (5)0.0061 (6)
C110.0479 (7)0.0588 (8)0.0545 (7)0.0020 (6)0.0198 (6)0.0055 (6)
C120.0563 (8)0.0691 (10)0.0619 (9)0.0089 (7)0.0190 (7)0.0216 (7)
C130.0589 (8)0.0881 (12)0.0467 (7)0.0016 (8)0.0102 (6)0.0154 (7)
C140.0633 (9)0.0749 (10)0.0465 (7)0.0083 (7)0.0122 (6)0.0003 (7)
C150.0595 (8)0.0576 (8)0.0495 (7)0.0028 (6)0.0118 (6)0.0045 (6)
C160.0676 (9)0.0522 (8)0.0618 (8)0.0008 (6)0.0223 (7)0.0114 (6)
C170.1228 (17)0.0633 (10)0.0751 (12)0.0140 (11)0.0391 (12)0.0023 (9)
N10.0501 (6)0.0636 (7)0.0401 (6)0.0099 (5)0.0029 (4)0.0047 (5)
O10.0566 (7)0.1113 (11)0.0531 (6)0.0140 (6)0.0042 (5)0.0188 (6)
O20.0769 (8)0.0774 (8)0.0537 (6)0.0279 (6)0.0031 (5)0.0077 (5)
O30.0680 (7)0.0566 (6)0.0695 (7)0.0020 (5)0.0307 (5)0.0010 (5)
O40.0680 (7)0.0697 (8)0.0905 (9)0.0052 (5)0.0356 (7)0.0014 (6)
Geometric parameters (Å, º) top
C1—C21.490 (3)C9—C101.5022 (18)
C1—H1A0.9600C10—C111.389 (2)
C1—H1B0.9600C10—C151.390 (2)
C1—H1C0.9600C11—C121.375 (2)
C2—O11.221 (2)C11—O31.4024 (18)
C2—C31.4848 (18)C12—C131.380 (3)
C3—C41.388 (2)C12—H120.9300
C3—C81.3890 (19)C13—C141.378 (2)
C4—C51.3759 (19)C13—H130.9300
C4—H40.9300C14—C151.384 (2)
C5—C61.3902 (19)C14—H140.9300
C5—H50.9300C15—H150.9300
C6—C71.382 (2)C16—O41.191 (2)
C6—N11.4101 (16)C16—O31.358 (2)
C7—C81.384 (2)C16—C171.497 (3)
C7—H70.9300C17—H17A0.9600
C8—H80.9300C17—H17B0.9600
C9—O21.2194 (18)C17—H17C0.9600
C9—N11.3619 (19)N1—H10.8600
C2—C1—H1A109.5C11—C10—C9120.41 (13)
C2—C1—H1B109.5C15—C10—C9121.66 (13)
H1A—C1—H1B109.5C12—C11—C10121.50 (14)
C2—C1—H1C109.5C12—C11—O3118.87 (14)
H1A—C1—H1C109.5C10—C11—O3119.49 (12)
H1B—C1—H1C109.5C11—C12—C13119.64 (15)
O1—C2—C3120.27 (15)C11—C12—H12120.2
O1—C2—C1119.83 (14)C13—C12—H12120.2
C3—C2—C1119.89 (14)C14—C13—C12120.25 (14)
C4—C3—C8118.28 (12)C14—C13—H13119.9
C4—C3—C2118.95 (13)C12—C13—H13119.9
C8—C3—C2122.74 (14)C13—C14—C15119.59 (15)
C5—C4—C3121.56 (13)C13—C14—H14120.2
C5—C4—H4119.2C15—C14—H14120.2
C3—C4—H4119.2C14—C15—C10121.16 (15)
C4—C5—C6119.58 (14)C14—C15—H15119.4
C4—C5—H5120.2C10—C15—H15119.4
C6—C5—H5120.2O4—C16—O3123.25 (16)
C7—C6—C5119.67 (13)O4—C16—C17126.61 (17)
C7—C6—N1118.01 (12)O3—C16—C17110.13 (15)
C5—C6—N1122.28 (13)C16—C17—H17A109.5
C6—C7—C8120.17 (13)C16—C17—H17B109.5
C6—C7—H7119.9H17A—C17—H17B109.5
C8—C7—H7119.9C16—C17—H17C109.5
C7—C8—C3120.73 (14)H17A—C17—H17C109.5
C7—C8—H8119.6H17B—C17—H17C109.5
C3—C8—H8119.6C9—N1—C6126.92 (12)
O2—C9—N1124.00 (13)C9—N1—H1116.5
O2—C9—C10121.78 (13)C6—N1—H1116.5
N1—C9—C10114.22 (12)C16—O3—C11116.38 (12)
C11—C10—C15117.84 (13)
O1—C2—C3—C44.4 (2)C9—C10—C11—C12176.85 (13)
C1—C2—C3—C4174.76 (17)C15—C10—C11—O3175.68 (13)
O1—C2—C3—C8177.69 (16)C9—C10—C11—O37.6 (2)
C1—C2—C3—C83.1 (2)C10—C11—C12—C131.0 (2)
C8—C3—C4—C50.4 (2)O3—C11—C12—C13176.59 (14)
C2—C3—C4—C5177.60 (15)C11—C12—C13—C140.7 (2)
C3—C4—C5—C61.1 (3)C12—C13—C14—C150.4 (3)
C4—C5—C6—C71.0 (2)C13—C14—C15—C101.3 (2)
C4—C5—C6—N1178.77 (15)C11—C10—C15—C141.1 (2)
C5—C6—C7—C80.2 (3)C9—C10—C15—C14175.65 (14)
N1—C6—C7—C8178.10 (15)O2—C9—N1—C61.7 (3)
C6—C7—C8—C30.5 (3)C10—C9—N1—C6178.01 (13)
C4—C3—C8—C70.4 (3)C7—C6—N1—C9156.85 (16)
C2—C3—C8—C7178.31 (16)C5—C6—N1—C925.3 (2)
O2—C9—C10—C1143.7 (2)O4—C16—O3—C112.0 (2)
N1—C9—C10—C11136.62 (15)C17—C16—O3—C11178.92 (13)
O2—C9—C10—C15132.97 (18)C12—C11—O3—C1685.66 (17)
N1—C9—C10—C1546.7 (2)C10—C11—O3—C1698.63 (16)
C15—C10—C11—C120.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
C5—H5···O20.932.352.8792 (19)116
C12—H12···O4i0.932.593.396 (2)145
N1—H1···O1ii0.862.082.9181 (16)164
C8—H8···Cg1iii0.933.204.0960 (15)164
Symmetry codes: (i) x+1, y+2, z; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+1/2.
 

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