Synthesis, crystal structure and in vitro anti-proliferative activity of 2-[(4-acetyl­phen­yl)carbamo­yl]phenyl acetate

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.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.134
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT481_ALERT_4_C Long D...A H-Bond Reported C8       ..CG1      .       4.10 Ang.

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         24 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          2 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

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

Crystal data

C17H15NO4	F(000) = 624
Mr = 297.30	Dx = 1.318 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 11.6286 (5) Å	Cell parameters from 5304 reflections
b = 8.6913 (4) Å	θ = 4.1–76.2°
c = 15.8180 (7) Å	µ = 0.78 mm^−1
β = 110.380 (5)°	T = 296 K
V = 1498.62 (12) Å^3	Needle, yellow
Z = 4	0.35 × 0.14 × 0.13 mm

Data collection

Agilent SuperNova, Dual, Cu at home/near, Atlas diffractometer	2612 reflections with I > 2σ(I)
ω scans	Rint = 0.027
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2019)	θmax = 76.9°, θmin = 4.1°
Tmin = 0.390, Tmax = 1.000	h = −14→14
17065 measured reflections	k = −10→10
3141 independent reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0761P)^2 + 0.1892P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
3141 reflections	Δρmax = 0.17 e Å^−3
201 parameters	Δρmin = −0.16 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5388 (2)	0.1466 (3)	0.63141 (13)	0.0868 (6)
H1A	0.587598	0.105244	0.689002	0.130*
H1B	0.498487	0.064212	0.591739	0.130*
H1C	0.478372	0.215398	0.638833	0.130*
C2	0.61923 (14)	0.23211 (19)	0.59205 (9)	0.0576 (4)
C3	0.56774 (12)	0.29253 (17)	0.49855 (9)	0.0505 (3)
C4	0.64622 (13)	0.36063 (19)	0.46058 (10)	0.0587 (4)
H4	0.728942	0.370691	0.495050	0.070*
C5	0.60455 (13)	0.41363 (19)	0.37314 (10)	0.0589 (4)
H5	0.658915	0.457351	0.348638	0.071*
C6	0.48068 (12)	0.40141 (16)	0.32165 (8)	0.0490 (3)
C7	0.40109 (13)	0.3340 (2)	0.35836 (10)	0.0624 (4)
H7	0.318208	0.325327	0.324040	0.075*
C8	0.44443 (13)	0.2795 (2)	0.44606 (10)	0.0619 (4)
H8	0.390386	0.233633	0.470096	0.074*
C9	0.48064 (13)	0.56038 (17)	0.19145 (9)	0.0539 (3)
C10	0.41025 (12)	0.58347 (17)	0.09278 (9)	0.0512 (3)
C11	0.38681 (13)	0.73080 (17)	0.05690 (10)	0.0532 (3)
C12	0.32771 (14)	0.7548 (2)	−0.03390 (11)	0.0629 (4)
H12	0.311768	0.854402	−0.056485	0.075*
C13	0.29218 (15)	0.6303 (2)	−0.09134 (10)	0.0668 (4)
H13	0.252995	0.646157	−0.152872	0.080*
C14	0.31454 (15)	0.4827 (2)	−0.05786 (10)	0.0634 (4)
H14	0.291076	0.398867	−0.096645	0.076*
C15	0.37213 (14)	0.45989 (19)	0.03382 (10)	0.0574 (4)
H15	0.385567	0.360130	0.056397	0.069*
C16	0.52387 (15)	0.93013 (18)	0.12475 (11)	0.0606 (4)
C17	0.5436 (2)	1.0612 (2)	0.18968 (14)	0.0858 (6)
H17A	0.559486	1.021628	0.249346	0.129*
H17B	0.471610	1.124674	0.172543	0.129*
H17C	0.612495	1.121222	0.188800	0.129*
N1	0.43273 (11)	0.45087 (15)	0.23117 (7)	0.0547 (3)
H1	0.366161	0.407257	0.197490	0.066*
O1	0.72755 (11)	0.25066 (17)	0.63648 (8)	0.0776 (4)
O2	0.57285 (12)	0.63430 (15)	0.23103 (8)	0.0745 (4)
O3	0.41633 (10)	0.85821 (13)	0.11491 (8)	0.0629 (3)
O4	0.58982 (12)	0.89231 (15)	0.08529 (9)	0.0739 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0814 (12)	0.1205 (18)	0.0571 (9)	0.0023 (11)	0.0223 (9)	0.0268 (10)
C2	0.0559 (8)	0.0687 (9)	0.0445 (7)	0.0146 (6)	0.0127 (6)	0.0053 (6)
C3	0.0473 (7)	0.0592 (8)	0.0412 (6)	0.0072 (5)	0.0108 (5)	0.0026 (5)
C4	0.0424 (7)	0.0737 (10)	0.0497 (7)	−0.0019 (6)	0.0030 (5)	0.0093 (6)
C5	0.0461 (7)	0.0745 (10)	0.0496 (7)	−0.0079 (6)	0.0087 (6)	0.0102 (6)
C6	0.0478 (7)	0.0533 (7)	0.0391 (6)	−0.0021 (5)	0.0067 (5)	0.0010 (5)
C7	0.0422 (7)	0.0892 (11)	0.0470 (7)	−0.0061 (7)	0.0045 (5)	0.0094 (7)
C8	0.0470 (7)	0.0872 (11)	0.0497 (7)	−0.0017 (7)	0.0146 (6)	0.0110 (7)
C9	0.0555 (7)	0.0560 (8)	0.0444 (7)	−0.0038 (6)	0.0101 (6)	0.0016 (5)
C10	0.0477 (7)	0.0579 (8)	0.0452 (7)	−0.0002 (5)	0.0127 (5)	0.0061 (6)
C11	0.0479 (7)	0.0588 (8)	0.0545 (7)	0.0020 (6)	0.0198 (6)	0.0055 (6)
C12	0.0563 (8)	0.0691 (10)	0.0619 (9)	0.0089 (7)	0.0190 (7)	0.0216 (7)
C13	0.0589 (8)	0.0881 (12)	0.0467 (7)	−0.0016 (8)	0.0102 (6)	0.0154 (7)
C14	0.0633 (9)	0.0749 (10)	0.0465 (7)	−0.0083 (7)	0.0122 (6)	−0.0003 (7)
C15	0.0595 (8)	0.0576 (8)	0.0495 (7)	−0.0028 (6)	0.0118 (6)	0.0045 (6)
C16	0.0676 (9)	0.0522 (8)	0.0618 (8)	0.0008 (6)	0.0223 (7)	0.0114 (6)
C17	0.1228 (17)	0.0633 (10)	0.0751 (12)	−0.0140 (11)	0.0391 (12)	−0.0023 (9)
N1	0.0501 (6)	0.0636 (7)	0.0401 (6)	−0.0099 (5)	0.0029 (4)	0.0047 (5)
O1	0.0566 (7)	0.1113 (11)	0.0531 (6)	0.0140 (6)	0.0042 (5)	0.0188 (6)
O2	0.0769 (8)	0.0774 (8)	0.0537 (6)	−0.0279 (6)	0.0031 (5)	0.0077 (5)
O3	0.0680 (7)	0.0566 (6)	0.0695 (7)	0.0020 (5)	0.0307 (5)	0.0010 (5)
O4	0.0680 (7)	0.0697 (8)	0.0905 (9)	−0.0052 (5)	0.0356 (7)	0.0014 (6)

Geometric parameters (Å, º)

C1—C2	1.490 (3)	C9—C10	1.5022 (18)
C1—H1A	0.9600	C10—C11	1.389 (2)
C1—H1B	0.9600	C10—C15	1.390 (2)
C1—H1C	0.9600	C11—C12	1.375 (2)
C2—O1	1.221 (2)	C11—O3	1.4024 (18)
C2—C3	1.4848 (18)	C12—C13	1.380 (3)
C3—C4	1.388 (2)	C12—H12	0.9300
C3—C8	1.3890 (19)	C13—C14	1.378 (2)
C4—C5	1.3759 (19)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.384 (2)
C5—C6	1.3902 (19)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.382 (2)	C16—O4	1.191 (2)
C6—N1	1.4101 (16)	C16—O3	1.358 (2)
C7—C8	1.384 (2)	C16—C17	1.497 (3)
C7—H7	0.9300	C17—H17A	0.9600
C8—H8	0.9300	C17—H17B	0.9600
C9—O2	1.2194 (18)	C17—H17C	0.9600
C9—N1	1.3619 (19)	N1—H1	0.8600
C2—C1—H1A	109.5	C11—C10—C9	120.41 (13)
C2—C1—H1B	109.5	C15—C10—C9	121.66 (13)
H1A—C1—H1B	109.5	C12—C11—C10	121.50 (14)
C2—C1—H1C	109.5	C12—C11—O3	118.87 (14)
H1A—C1—H1C	109.5	C10—C11—O3	119.49 (12)
H1B—C1—H1C	109.5	C11—C12—C13	119.64 (15)
O1—C2—C3	120.27 (15)	C11—C12—H12	120.2
O1—C2—C1	119.83 (14)	C13—C12—H12	120.2
C3—C2—C1	119.89 (14)	C14—C13—C12	120.25 (14)
C4—C3—C8	118.28 (12)	C14—C13—H13	119.9
C4—C3—C2	118.95 (13)	C12—C13—H13	119.9
C8—C3—C2	122.74 (14)	C13—C14—C15	119.59 (15)
C5—C4—C3	121.56 (13)	C13—C14—H14	120.2
C5—C4—H4	119.2	C15—C14—H14	120.2
C3—C4—H4	119.2	C14—C15—C10	121.16 (15)
C4—C5—C6	119.58 (14)	C14—C15—H15	119.4
C4—C5—H5	120.2	C10—C15—H15	119.4
C6—C5—H5	120.2	O4—C16—O3	123.25 (16)
C7—C6—C5	119.67 (13)	O4—C16—C17	126.61 (17)
C7—C6—N1	118.01 (12)	O3—C16—C17	110.13 (15)
C5—C6—N1	122.28 (13)	C16—C17—H17A	109.5
C6—C7—C8	120.17 (13)	C16—C17—H17B	109.5
C6—C7—H7	119.9	H17A—C17—H17B	109.5
C8—C7—H7	119.9	C16—C17—H17C	109.5
C7—C8—C3	120.73 (14)	H17A—C17—H17C	109.5
C7—C8—H8	119.6	H17B—C17—H17C	109.5
C3—C8—H8	119.6	C9—N1—C6	126.92 (12)
O2—C9—N1	124.00 (13)	C9—N1—H1	116.5
O2—C9—C10	121.78 (13)	C6—N1—H1	116.5
N1—C9—C10	114.22 (12)	C16—O3—C11	116.38 (12)
C11—C10—C15	117.84 (13)
O1—C2—C3—C4	4.4 (2)	C9—C10—C11—C12	176.85 (13)
C1—C2—C3—C4	−174.76 (17)	C15—C10—C11—O3	175.68 (13)
O1—C2—C3—C8	−177.69 (16)	C9—C10—C11—O3	−7.6 (2)
C1—C2—C3—C8	3.1 (2)	C10—C11—C12—C13	−1.0 (2)
C8—C3—C4—C5	−0.4 (2)	O3—C11—C12—C13	−176.59 (14)
C2—C3—C4—C5	177.60 (15)	C11—C12—C13—C14	0.7 (2)
C3—C4—C5—C6	1.1 (3)	C12—C13—C14—C15	0.4 (3)
C4—C5—C6—C7	−1.0 (2)	C13—C14—C15—C10	−1.3 (2)
C4—C5—C6—N1	−178.77 (15)	C11—C10—C15—C14	1.1 (2)
C5—C6—C7—C8	0.2 (3)	C9—C10—C15—C14	−175.65 (14)
N1—C6—C7—C8	178.10 (15)	O2—C9—N1—C6	−1.7 (3)
C6—C7—C8—C3	0.5 (3)	C10—C9—N1—C6	178.01 (13)
C4—C3—C8—C7	−0.4 (3)	C7—C6—N1—C9	156.85 (16)
C2—C3—C8—C7	−178.31 (16)	C5—C6—N1—C9	−25.3 (2)
O2—C9—C10—C11	−43.7 (2)	O4—C16—O3—C11	2.0 (2)
N1—C9—C10—C11	136.62 (15)	C17—C16—O3—C11	−178.92 (13)
O2—C9—C10—C15	132.97 (18)	C12—C11—O3—C16	−85.66 (17)
N1—C9—C10—C15	−46.7 (2)	C10—C11—O3—C16	98.63 (16)
C15—C10—C11—C12	0.1 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2	0.93	2.35	2.8792 (19)	116
C12—H12···O4^i	0.93	2.59	3.396 (2)	145
N1—H1···O1^ii	0.86	2.08	2.9181 (16)	164
C8—H8···Cg1^iii	0.93	3.20	4.0960 (15)	164

Symmetry codes: (i) −x+1, −y+2, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.