trans-rac-2-Hexyl-1-oxo-3-(2-pyrid­yl)-1,2,3,4-tetra­hydro­isoquinoline-4-carboxylic acid

The title compound, C₂₁H₂₄N₂O₃, crystallizes as a racemic mixture of R,R and S,S enanti­omers. The three-dimensional packing is stabilized by a system of hydrogen bonds and weak C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 290 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.089
• wR factor = 0.292
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.292
PLAT084_ALERT_2_C High R2 Value ..................................       0.29
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.00 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.56 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C18    -   C19     ..       5.88 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C20
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C19    -   C20    ...       1.38 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  O3      ..       2.69 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

trans-rac-2-Hexyl-1-oxo-3-(2-pyridyl)-1,2,3,4-tetrahydroisoquinoline-4- carboxylic acid

Crystal data

C21H24N2O3	F(000) = 752
Mr = 352.42	Dx = 1.206 Mg m^−3
Monoclinic, P21/n	Melting point: 389 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.8917 (4) Å	Cell parameters from 22 reflections
b = 12.9205 (9) Å	θ = 8.2–11.6°
c = 15.5882 (9) Å	µ = 0.08 mm^−1
β = 103.216 (6)°	T = 290 K
V = 1939.5 (2) Å^3	Prism, colourless
Z = 4	0.5 × 0.25 × 0.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.035
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.1°
Graphite monochromator	h = −12→11
Non–profiled ω/2θ scans	k = 0→15
3907 measured reflections	l = 0→19
3770 independent reflections	3 standard reflections every 200 reflections
2371 reflections with I > 2σ(I)	intensity decay: −1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.292	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1806P)^2 + 0.5652P] where P = (Fo^2 + 2Fc^2)/3
3770 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. The ¹H NMR spectrum of (I) was obtained on a Bruker Advance DRX-250 spectrometer at 250.13 MHz in DMSO_d6 at 293 K with tetramethylsilane as internal standard. ¹H NMR (250 MHz, DMSO_d6, p.p.m.): 0.81–0.92 (3H, m, –CH₃), 1.18–1.35 (6H, m, –CH₂–), 1.45–1.63 (2H, m, –CH₂–), 2.73–2.84 (1H, m, –CH₂–), 4.03–4.15 (1H, m, –CH₂–), 4.41 (1H, d, J = 1.0 Hz, H8), 5.33 (1H, d, J = 1.0 Hz, H9), 7.01 (1H, dd, J = 7.9 Hz, Ph—H), 7.17–7.21 (2H, m, Ph—H), 7.30–7.39 (2H, m, Pyr-H), 7.66 (1H, dt, J = 1.8 and 7.8 Hz, Ph—H), 7.87 (1H, dd, J = 2.3 and 6.8 Hz, Ph—H), 8.48 (1H, dm, J = 4.8 Hz, Pyr-H).

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5371 (2)	0.32470 (19)	0.75690 (19)	0.0754 (8)
H1	0.5690	0.2580	0.7450	0.113*
O2	0.9082 (2)	0.63213 (18)	0.77527 (18)	0.0671 (7)
O3	0.7486 (3)	0.3350 (2)	0.8398 (2)	0.0922 (11)
N1	0.6857 (3)	0.5773 (2)	0.73663 (18)	0.0525 (7)
N2	0.3546 (3)	0.6176 (3)	0.8012 (2)	0.0724 (9)
C1	0.8024 (3)	0.6005 (2)	0.7976 (2)	0.0518 (8)
C2	0.8010 (3)	0.5845 (2)	0.8909 (2)	0.0507 (8)
C3	0.9065 (4)	0.6258 (3)	0.9571 (3)	0.0648 (10)
H3	0.9749	0.6668	0.9421	0.078*
C4	0.9102 (4)	0.6065 (3)	1.0438 (3)	0.0767 (12)
H4	0.9805	0.6348	1.0875	0.092*
C5	0.8093 (4)	0.5446 (3)	1.0666 (3)	0.0755 (11)
H5	0.8125	0.5313	1.1256	0.091*
C6	0.7053 (4)	0.5031 (3)	1.0027 (2)	0.0639 (9)
H6	0.6382	0.4615	1.0185	0.077*
C7	0.6993 (3)	0.5228 (2)	0.9143 (2)	0.0507 (8)
C8	0.5907 (3)	0.4758 (2)	0.8417 (2)	0.0510 (8)
H8	0.5059	0.4662	0.8633	0.061*
C9	0.5578 (3)	0.5491 (2)	0.7628 (2)	0.0513 (8)
H9	0.5001	0.5106	0.7136	0.062*
C10	0.4735 (3)	0.6428 (3)	0.7799 (2)	0.0537 (8)
C11	0.2733 (4)	0.6959 (4)	0.8148 (3)	0.0884 (14)
H11	0.1908	0.6800	0.8309	0.106*
C12	0.3050 (4)	0.7987 (4)	0.8062 (3)	0.0827 (13)
H12	0.2448	0.8505	0.8156	0.099*
C13	0.4258 (4)	0.8227 (3)	0.7837 (3)	0.0710 (10)
H13	0.4501	0.8915	0.7782	0.085*
C14	0.5132 (3)	0.7436 (3)	0.7688 (2)	0.0614 (9)
H14	0.5955	0.7580	0.7519	0.074*
C15	0.6356 (3)	0.3708 (2)	0.8141 (2)	0.0541 (8)
C16	0.6813 (4)	0.5874 (3)	0.6430 (2)	0.0612 (9)
H16A	0.7462	0.6408	0.6350	0.073*
H16B	0.5890	0.6096	0.6127	0.073*
C17	0.7161 (4)	0.4887 (3)	0.6013 (3)	0.0732 (11)
H17A	0.6496	0.4357	0.6077	0.088*
H17B	0.8074	0.4654	0.6325	0.088*
C18	0.7151 (5)	0.5006 (4)	0.5049 (3)	0.0907 (14)
H18A	0.7821	0.5535	0.4992	0.109*
H18B	0.6242	0.5254	0.4746	0.109*
C19	0.7477 (7)	0.4033 (6)	0.4583 (4)	0.125 (2)
H19A	0.6821	0.3500	0.4655	0.150*
H19B	0.7318	0.4182	0.3959	0.150*
C20	0.8796 (8)	0.3637 (6)	0.4859 (6)	0.152 (3)
H20A	0.8880	0.3390	0.5456	0.182*
H20B	0.9433	0.4214	0.4894	0.182*
C21	0.9324 (7)	0.2802 (5)	0.4374 (5)	0.145 (3)
H21A	1.0229	0.2593	0.4697	0.217*
H21B	0.9383	0.3050	0.3803	0.217*
H21C	0.8704	0.2221	0.4307	0.217*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0511 (14)	0.0528 (14)	0.116 (2)	−0.0002 (11)	0.0064 (13)	−0.0203 (14)
O2	0.0424 (12)	0.0561 (14)	0.107 (2)	0.0028 (10)	0.0272 (12)	0.0200 (13)
O3	0.0488 (15)	0.0600 (16)	0.156 (3)	0.0105 (12)	−0.0001 (16)	−0.0304 (17)
N1	0.0429 (14)	0.0500 (15)	0.0673 (18)	0.0035 (11)	0.0182 (12)	0.0040 (12)
N2	0.0455 (15)	0.070 (2)	0.107 (2)	0.0130 (14)	0.0296 (16)	0.0178 (17)
C1	0.0425 (16)	0.0380 (15)	0.076 (2)	0.0063 (12)	0.0157 (15)	0.0073 (14)
C2	0.0433 (16)	0.0392 (15)	0.069 (2)	0.0070 (12)	0.0122 (14)	−0.0014 (14)
C3	0.0492 (18)	0.0500 (19)	0.091 (3)	−0.0005 (15)	0.0075 (18)	−0.0072 (18)
C4	0.066 (2)	0.071 (2)	0.082 (3)	0.005 (2)	−0.007 (2)	−0.017 (2)
C5	0.077 (3)	0.078 (3)	0.070 (2)	0.007 (2)	0.013 (2)	−0.008 (2)
C6	0.060 (2)	0.061 (2)	0.071 (2)	0.0043 (17)	0.0159 (17)	0.0045 (18)
C7	0.0441 (16)	0.0395 (15)	0.069 (2)	0.0081 (13)	0.0133 (14)	−0.0011 (14)
C8	0.0396 (15)	0.0436 (16)	0.073 (2)	0.0007 (12)	0.0202 (14)	−0.0002 (15)
C9	0.0394 (15)	0.0472 (17)	0.068 (2)	0.0010 (13)	0.0133 (14)	−0.0005 (15)
C10	0.0397 (15)	0.0515 (18)	0.068 (2)	0.0064 (13)	0.0096 (14)	0.0069 (15)
C11	0.053 (2)	0.092 (3)	0.129 (4)	0.024 (2)	0.040 (2)	0.021 (3)
C12	0.062 (2)	0.076 (3)	0.110 (3)	0.029 (2)	0.020 (2)	0.003 (2)
C13	0.065 (2)	0.054 (2)	0.089 (3)	0.0152 (17)	0.0065 (19)	0.0004 (18)
C14	0.0455 (17)	0.0538 (19)	0.084 (2)	0.0050 (14)	0.0128 (16)	0.0029 (17)
C15	0.0397 (16)	0.0412 (16)	0.083 (2)	−0.0043 (13)	0.0165 (15)	−0.0022 (15)
C16	0.0565 (19)	0.055 (2)	0.075 (2)	0.0021 (16)	0.0205 (17)	0.0030 (17)
C17	0.074 (2)	0.066 (2)	0.082 (3)	0.0041 (19)	0.025 (2)	−0.0049 (19)
C18	0.082 (3)	0.100 (4)	0.093 (3)	0.011 (3)	0.026 (2)	−0.014 (3)
C19	0.106 (4)	0.158 (6)	0.116 (4)	0.012 (4)	0.035 (4)	−0.027 (4)
C20	0.130 (6)	0.134 (6)	0.176 (7)	0.035 (5)	0.002 (5)	−0.039 (5)
C21	0.137 (6)	0.128 (5)	0.183 (7)	0.008 (4)	0.065 (5)	−0.058 (5)

Geometric parameters (Å, º)

O1—C15	1.305 (4)	C10—C14	1.382 (5)
O1—H1	0.9502	C11—C12	1.379 (6)
O2—C1	1.245 (4)	C11—H11	0.9300
O3—C15	1.191 (4)	C12—C13	1.356 (6)
N1—C1	1.351 (4)	C12—H12	0.9300
N1—C16	1.456 (4)	C13—C14	1.392 (5)
N1—C9	1.461 (4)	C13—H13	0.9300
N2—C10	1.334 (4)	C14—H14	0.9300
N2—C11	1.339 (5)	C16—C17	1.507 (5)
C1—C2	1.472 (5)	C16—H16A	0.9700
C2—C3	1.395 (5)	C16—H16B	0.9700
C2—C7	1.396 (4)	C17—C18	1.507 (6)
C3—C4	1.366 (6)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.387 (6)	C18—C19	1.523 (7)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.367 (5)	C18—H18B	0.9700
C5—H5	0.9300	C19—C20	1.376 (8)
C6—C7	1.389 (5)	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—C8	1.500 (5)	C20—C21	1.479 (8)
C8—C15	1.519 (4)	C20—H20A	0.9700
C8—C9	1.527 (5)	C20—H20B	0.9700
C8—H8	0.9800	C21—H21A	0.9600
C9—C10	1.529 (4)	C21—H21B	0.9600
C9—H9	0.9800	C21—H21C	0.9600
C15—O1—H1	108.6	C11—C12—H12	120.7
C1—N1—C16	120.7 (3)	C12—C13—C14	119.5 (4)
C1—N1—C9	120.9 (3)	C12—C13—H13	120.2
C16—N1—C9	118.2 (3)	C14—C13—H13	120.2
C10—N2—C11	116.8 (3)	C10—C14—C13	117.8 (3)
O2—C1—N1	120.9 (3)	C10—C14—H14	121.1
O2—C1—C2	121.4 (3)	C13—C14—H14	121.1
N1—C1—C2	117.7 (3)	O3—C15—O1	123.3 (3)
C3—C2—C7	119.1 (3)	O3—C15—C8	124.4 (3)
C3—C2—C1	120.2 (3)	O1—C15—C8	112.3 (3)
C7—C2—C1	120.6 (3)	N1—C16—C17	113.5 (3)
C4—C3—C2	120.5 (4)	N1—C16—H16A	108.9
C4—C3—H3	119.7	C17—C16—H16A	108.9
C2—C3—H3	119.7	N1—C16—H16B	108.9
C3—C4—C5	120.0 (4)	C17—C16—H16B	108.9
C3—C4—H4	120.0	H16A—C16—H16B	107.7
C5—C4—H4	120.0	C16—C17—C18	113.1 (3)
C6—C5—C4	120.4 (4)	C16—C17—H17A	109.0
C6—C5—H5	119.8	C18—C17—H17A	109.0
C4—C5—H5	119.8	C16—C17—H17B	109.0
C5—C6—C7	120.3 (4)	C18—C17—H17B	109.0
C5—C6—H6	119.8	H17A—C17—H17B	107.8
C7—C6—H6	119.8	C17—C18—C19	115.9 (5)
C6—C7—C2	119.6 (3)	C17—C18—H18A	108.3
C6—C7—C8	122.4 (3)	C19—C18—H18A	108.3
C2—C7—C8	117.9 (3)	C17—C18—H18B	108.3
C7—C8—C15	111.7 (2)	C19—C18—H18B	108.3
C7—C8—C9	109.9 (3)	H18A—C18—H18B	107.4
C15—C8—C9	110.3 (3)	C20—C19—C18	116.6 (6)
C7—C8—H8	108.3	C20—C19—H19A	108.1
C15—C8—H8	108.3	C18—C19—H19A	108.1
C9—C8—H8	108.3	C20—C19—H19B	108.1
N1—C9—C8	110.0 (2)	C18—C19—H19B	108.1
N1—C9—C10	113.1 (3)	H19A—C19—H19B	107.3
C8—C9—C10	112.0 (3)	C19—C20—C21	122.2 (7)
N1—C9—H9	107.1	C19—C20—H20A	106.8
C8—C9—H9	107.1	C21—C20—H20A	106.8
C10—C9—H9	107.1	C19—C20—H20B	106.8
N2—C10—C14	123.6 (3)	C21—C20—H20B	106.8
N2—C10—C9	113.4 (3)	H20A—C20—H20B	106.6
C14—C10—C9	122.9 (3)	C20—C21—H21A	109.5
N2—C11—C12	123.7 (4)	C20—C21—H21B	109.5
N2—C11—H11	118.2	H21A—C21—H21B	109.5
C12—C11—H11	118.2	C20—C21—H21C	109.5
C13—C12—C11	118.6 (4)	H21A—C21—H21C	109.5
C13—C12—H12	120.7	H21B—C21—H21C	109.5
C9—N1—C1—O2	−174.5 (3)	C10—N2—C11—H11	−178.7
C9—N1—C1—C2	7.1 (4)	C1—C2—C3—H3	3.6
C16—N1—C1—O2	0.7 (4)	C7—C2—C3—H3	179.8
C16—N1—C1—C2	−177.6 (3)	C2—C3—C4—H4	−179.4
C1—N1—C9—C8	−42.5 (4)	H3—C3—C4—C5	−179.4
C1—N1—C9—C10	83.5 (3)	H3—C3—C4—H4	0.6
C16—N1—C9—C8	142.1 (3)	C3—C4—C5—H5	179.6
C16—N1—C9—C10	−91.8 (3)	H4—C4—C5—C6	179.6
C1—N1—C16—C17	93.3 (4)	H4—C4—C5—H5	−0.4
C9—N1—C16—C17	−91.3 (4)	C4—C5—C6—H6	179.8
C11—N2—C10—C9	−178.2 (3)	H5—C5—C6—C7	179.8
C11—N2—C10—C14	−2.2 (6)	H5—C5—C6—H6	−0.2
C10—N2—C11—C12	1.3 (7)	H6—C6—C7—C2	−179.4
O2—C1—C2—C3	14.4 (4)	H6—C6—C7—C8	−2.5
O2—C1—C2—C7	−161.6 (3)	C2—C7—C8—H8	−151.8
N1—C1—C2—C3	−167.2 (3)	C6—C7—C8—H8	31.3
N1—C1—C2—C7	16.7 (4)	C7—C8—C9—H9	169.8
C1—C2—C3—C4	−176.4 (3)	C15—C8—C9—H9	46.2
C7—C2—C3—C4	−0.2 (5)	H8—C8—C9—N1	171.8
C1—C2—C7—C6	175.8 (3)	H8—C8—C9—C10	45.1
C1—C2—C7—C8	−1.3 (4)	H8—C8—C9—H9	−72.1
C3—C2—C7—C6	−0.4 (4)	H8—C8—C15—O1	54.8
C3—C2—C7—C8	−177.4 (3)	H8—C8—C15—O3	−126.7
C2—C3—C4—C5	0.6 (6)	H9—C9—C10—N2	60.2
C3—C4—C5—C6	−0.4 (6)	H9—C9—C10—C14	−115.9
C4—C5—C6—C7	−0.2 (6)	N2—C10—C14—H14	−177.7
C5—C6—C7—C2	0.6 (5)	C9—C10—C14—H14	−2.0
C5—C6—C7—C8	177.5 (3)	N2—C11—C12—H12	179.3
C2—C7—C8—C9	−33.7 (4)	H11—C11—C12—C13	179.3
C2—C7—C8—C15	89.1 (3)	H11—C11—C12—H12	−0.7
C6—C7—C8—C9	149.3 (3)	C11—C12—C13—H13	−179.2
C6—C7—C8—C15	−87.9 (4)	H12—C12—C13—C14	−179.2
C7—C8—C9—N1	53.7 (3)	H12—C12—C13—H13	0.8
C7—C8—C9—C10	−73.0 (3)	C12—C13—C14—H14	178.4
C15—C8—C9—N1	−69.9 (3)	H13—C13—C14—C10	178.4
C15—C8—C9—C10	163.4 (2)	H13—C13—C14—H14	−1.6
C7—C8—C15—O1	174.0 (3)	N1—C16—C17—H17A	60.2
C7—C8—C15—O3	−7.6 (5)	N1—C16—C17—H17B	−57.1
C9—C8—C15—O1	−63.5 (4)	H16A—C16—C17—C18	−57.0
C9—C8—C15—O3	114.9 (4)	H16A—C16—C17—H17A	−178.4
N1—C9—C10—N2	178.1 (3)	H16A—C16—C17—H17B	64.3
N1—C9—C10—C14	2.0 (5)	H16B—C16—C17—C18	60.1
C8—C9—C10—N2	−57.0 (4)	H16B—C16—C17—H17A	−61.2
C8—C9—C10—C14	126.9 (3)	H16B—C16—C17—H17B	−178.5
N2—C10—C14—C13	2.3 (6)	C16—C17—C18—H18A	58.8
C9—C10—C14—C13	178.0 (3)	C16—C17—C18—H18B	−57.4
N2—C11—C12—C13	−0.7 (8)	H17A—C17—C18—C19	−57.9
C11—C12—C13—C14	0.8 (7)	H17A—C17—C18—H18A	−179.8
C12—C13—C14—C10	−1.6 (6)	H17A—C17—C18—H18B	64.0
N1—C16—C17—C18	−178.4 (3)	H17B—C17—C18—C19	59.4
C16—C17—C18—C19	−179.3 (4)	H17B—C17—C18—H18A	−62.5
C17—C18—C19—C20	−65.4 (8)	H17B—C17—C18—H18B	−178.7
C18—C19—C20—C21	−169.9 (7)	C17—C18—C19—H19A	56.6
H1—O1—C15—O3	5.2	C17—C18—C19—H19B	172.5
H1—O1—C15—C8	−176.4	H18A—C18—C19—C20	56.4
C1—N1—C9—H9	−158.6	H18A—C18—C19—H19A	178.5
C16—N1—C9—H9	26.0	H18A—C18—C19—H19B	−65.6
C1—N1—C16—H16A	−28.1	H18B—C18—C19—C20	172.7
C1—N1—C16—H16B	−145.3	H18B—C18—C19—H19A	−65.3
C9—N1—C16—H16A	147.3	H18B—C18—C19—H19B	50.6
C9—N1—C16—H16B	30.1	C18—C19—C20—H20A	66.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.95	1.68	2.619 (2)	168
C4—H4···O3^ii	0.93	2.69	3.529 (3)	151
C14—H14···O3^iii	0.93	2.53	3.411 (3)	157
C16—H16A···O3^iii	0.97	2.54	3.271 (3)	132

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2.