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The mol­ecule of the title compound, C17H13NO4S, is non-planar. In the propanoic acid group, the average C-C bond length and the average C-C-C bond angle are 1.501 (1) Å and 110.9 (3)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007281/cm6036sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007281/cm6036Isup2.hkl
Contains datablock I

CCDC reference: 214601

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.190
  • Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.29 From the CIF: _reflns_number_total 2818 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3067 Completeness (_total/calc) 91.88% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title compound, (I), showed higher analgesic activity than aspirin and has an anti-inflamatory activity as well as indometacin (Dündar et al., 2003). In this study, the crystal structure of (I) has been determined by X-ray diffraction.

The atom-numbering scheme of (I) is shown in Fig 2. Selected bond lengths and angles are listed in Table 1. The lengtening of the S1—C14 bond distance [1.781 (4) Å] versus the S1—C10 bond distance [1.743 (4) Å] is 0.034 (3) Å [S1—C7 = 1.776 (3) Å and S1—C6 = 1.742 (3) Å in methyl 3-(5-chloro-2-oxo-1.3-benzothiazol-3(2H)-yl)propanoate (Aydın, 2002)]. This case may be described in term of the steric interaction.

Maximum deviations from the mean plane through benzothiazole (N1/C11/C12/C13/C8/C9/C10/S1/C14, which is almost planar) are −0.016 (3) and 0.017 (3) Å for N1 and C12, respectively. The dihedral angle between the benzothiazole and the phenyl ring (C1–C6) is 49.2 (1)°.

The quantum-chemical calculation was performed by using the PM3 method and it was calculated that the charges at the N1, S1, O1, O2, O3 and O4 atoms are 0.0353, 0.1836, −0.2321, −0.2989, −0.2958 and −0.2186 e-, respectively. Final heat of formation of the title compound is −61.49 kcal and its total energy is −3735.42 eV. The values of the HOMO and LUMO energies are −9.19104 and −0.83799 eV, respectively. The molecule dipole moment calculated is 4.641 Debye.

Hydrogen-bonding contacts are summarized in Table 2. The crystal structure is stabilized by by C—H···O and O—H···O type of intermolecular hydrogen-bond networks.

Experimental top

3-(6-Benzoyl-2-benzothiazolinon-3-yl)propanenitrile (10.0 mmol) was added to N,N-dimethylformamide–water–sulfuric acid (1:1:2) mixture (50 ml). After stirring at room temperature for 2 h, the mixture was refluxed for 4 h. The mixture cooled to the room temperature was poured into ice water (100 g). The precipitate formed was filtered by suction filtration, washed with water, dried and crystallized from ethanol–water (yield 75%, m.p. 456–457 K).

Refinement top

All H atoms were placed in geometrically idealized positions, but not refined. The three-dimensional Bragg reflections of the title compound were collected on an Enraf–Nonius CAD-4 diffractometer using Mo Kα radiation. Due to the low quality of the crystal, the reflections from the planes with the high indices of the crystal measured were very weak in intensity. Therefore, data collection was stopped at θmax = 26.29°.

Computing details top

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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A displacement ellipsoid plot (SHELXL97; Sheldrick, 1997) of the title compound with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the crystal packing and hydrogen-bond contacts (dotted lines)) along the b axis.
3-(6-Benzoyl-2-oxo-2,3-dihydro-2-benzothiazol-3-yl)propanoic acid top
Crystal data top
C17H13NO4SF(000) = 680
Mr = 327.35Dx = 1.439 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 37 reflections
a = 9.352 (5) Åθ = 9.4–32.3°
b = 12.921 (5) ŵ = 0.23 mm1
c = 12.908 (5) ÅT = 293 K
β = 104.370 (5)°Prism, yellow
V = 1511.0 (12) Å30.25 × 0.20 × 0.15 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.002
ω/2θ scansθmax = 26.3°, θmin = 2.3°
Absorption correction: part of the refinement model (ΔF)
(Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters
h = 1111
Tmin = 0.944, Tmax = 0.966k = 160
4283 measured reflectionsl = 016
2818 independent reflections3 standard reflections every 120 min
1906 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters not refined
S = 1.06 w = 1/[σ2(Fo2) + (0.1078P)2 + 0.8574P]
where P = (Fo2 + 2Fc2)/3
2818 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C17H13NO4SV = 1511.0 (12) Å3
Mr = 327.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.352 (5) ŵ = 0.23 mm1
b = 12.921 (5) ÅT = 293 K
c = 12.908 (5) Å0.25 × 0.20 × 0.15 mm
β = 104.370 (5)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1906 reflections with I > 2σ(I)
Absorption correction: part of the refinement model (ΔF)
(Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters
Rint = 0.002
Tmin = 0.944, Tmax = 0.9663 standard reflections every 120 min
4283 measured reflections intensity decay: 2%
2818 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.190H-atom parameters not refined
S = 1.06Δρmax = 0.34 e Å3
2818 reflectionsΔρmin = 0.38 e Å3
208 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.16141 (10)0.07368 (6)0.52484 (8)0.0525 (3)
O10.0988 (3)0.08710 (17)0.0959 (2)0.0551 (9)
O20.3058 (3)0.17629 (19)0.6990 (2)0.0577 (9)
O30.3897 (3)0.5280 (2)0.7265 (2)0.0606 (9)
O40.5923 (3)0.5152 (2)0.6670 (3)0.0680 (10)
N10.1975 (3)0.27124 (19)0.5482 (2)0.0421 (9)
C10.3210 (3)0.3116 (2)0.1052 (3)0.0400 (10)
C20.4365 (4)0.3652 (3)0.0392 (3)0.0494 (11)
C30.4752 (4)0.3461 (3)0.0677 (3)0.0584 (14)
C40.3995 (4)0.2728 (3)0.1126 (3)0.0644 (14)
C50.2839 (4)0.2192 (3)0.0472 (3)0.0531 (12)
C60.2432 (3)0.2377 (2)0.0625 (3)0.0394 (10)
C70.1266 (3)0.1711 (2)0.1305 (3)0.0396 (10)
C80.0450 (3)0.2041 (2)0.2392 (3)0.0403 (10)
C90.0066 (3)0.1270 (2)0.3153 (3)0.0417 (10)
C100.0868 (3)0.1544 (2)0.4168 (3)0.0398 (10)
C110.1177 (3)0.2589 (2)0.4433 (3)0.0374 (10)
C120.0697 (3)0.3351 (2)0.3679 (3)0.0433 (10)
C130.0118 (3)0.3075 (2)0.2676 (3)0.0422 (10)
C140.2349 (3)0.1816 (3)0.6067 (3)0.0445 (10)
C150.2440 (3)0.3710 (3)0.6008 (3)0.0454 (11)
C160.3968 (4)0.4018 (3)0.5933 (3)0.0515 (11)
C170.4557 (4)0.4880 (3)0.6686 (3)0.0434 (11)
H10.295230.324950.178320.0480*
H20.487840.414520.068070.0592*
H30.553160.382370.111340.0701*
H40.426430.260040.185780.0773*
H50.232730.170280.076770.0637*
H90.012910.057740.297930.0501*
H120.092040.404240.384550.0520*
H130.045770.359070.217230.0507*
H15A0.242530.366240.675560.0545*
H15B0.174360.424160.567850.0545*
H16A0.462320.342580.610050.0621*
H16B0.393410.423370.520760.0621*
H400.619610.563190.708840.1021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0494 (5)0.0362 (5)0.0651 (7)0.0012 (3)0.0015 (4)0.0117 (4)
O10.0592 (15)0.0370 (13)0.0674 (18)0.0052 (10)0.0127 (13)0.0118 (11)
O20.0506 (14)0.0572 (15)0.0599 (19)0.0056 (12)0.0035 (13)0.0097 (12)
O30.0667 (16)0.0562 (15)0.0648 (18)0.0068 (13)0.0277 (14)0.0197 (13)
O40.0545 (15)0.0770 (19)0.076 (2)0.0221 (14)0.0229 (14)0.0319 (15)
N10.0371 (13)0.0365 (14)0.0501 (18)0.0005 (11)0.0060 (12)0.0027 (12)
C10.0441 (17)0.0364 (16)0.0406 (19)0.0025 (13)0.0126 (14)0.0037 (13)
C20.0491 (19)0.0402 (18)0.062 (2)0.0049 (14)0.0196 (17)0.0028 (16)
C30.055 (2)0.058 (2)0.057 (3)0.0084 (17)0.0041 (18)0.0060 (18)
C40.065 (2)0.079 (3)0.046 (2)0.007 (2)0.0077 (19)0.0056 (19)
C50.052 (2)0.056 (2)0.053 (2)0.0032 (16)0.0161 (17)0.0107 (17)
C60.0382 (15)0.0359 (15)0.046 (2)0.0057 (13)0.0140 (14)0.0026 (13)
C70.0370 (15)0.0351 (16)0.049 (2)0.0034 (12)0.0148 (14)0.0035 (14)
C80.0370 (15)0.0310 (15)0.055 (2)0.0001 (12)0.0152 (14)0.0017 (14)
C90.0406 (17)0.0276 (15)0.055 (2)0.0020 (12)0.0085 (15)0.0032 (14)
C100.0375 (15)0.0293 (15)0.051 (2)0.0014 (12)0.0081 (14)0.0065 (14)
C110.0329 (14)0.0339 (15)0.045 (2)0.0014 (12)0.0089 (13)0.0008 (13)
C120.0461 (17)0.0283 (15)0.055 (2)0.0037 (13)0.0116 (16)0.0018 (14)
C130.0430 (17)0.0301 (15)0.052 (2)0.0005 (13)0.0092 (15)0.0039 (14)
C140.0319 (15)0.0482 (19)0.051 (2)0.0030 (14)0.0055 (15)0.0095 (15)
C150.0424 (17)0.0417 (18)0.051 (2)0.0016 (14)0.0095 (15)0.0077 (14)
C160.051 (2)0.0479 (19)0.060 (2)0.0068 (16)0.0220 (18)0.0155 (17)
C170.0460 (17)0.0422 (18)0.041 (2)0.0026 (14)0.0089 (15)0.0006 (14)
Geometric parameters (Å, º) top
S1—C101.743 (4)C8—C131.400 (4)
S1—C141.781 (4)C9—C101.384 (5)
O1—C71.226 (4)C10—C111.405 (4)
O2—C141.213 (5)C11—C121.379 (5)
O3—C171.198 (5)C12—C131.376 (5)
O4—C171.330 (5)C15—C161.509 (5)
O4—H400.8203C16—C171.491 (5)
N1—C111.384 (5)C1—H10.9305
N1—C151.471 (5)C2—H20.9297
N1—C141.379 (5)C3—H30.9299
C1—C21.384 (5)C4—H40.9300
C1—C61.394 (4)C5—H50.9300
C2—C31.359 (5)C9—H90.9296
C3—C41.392 (5)C12—H120.9304
C4—C51.381 (5)C13—H130.9301
C5—C61.393 (5)C15—H15A0.9705
C6—C71.492 (4)C15—H15B0.9692
C7—C81.484 (5)C16—H16A0.9705
C8—C91.398 (5)C16—H16B0.9699
S1···S1i3.491 (2)C2···H16Axii3.0609
S1···H2ii3.1915C6···H132.8332
O1···C15iii3.236 (4)C8···H12.7603
O1···C12iv3.291 (4)C12···H15B2.7730
O2···C163.414 (5)C12···H5vi3.0850
O2···O4v2.723 (4)C13···H12.6246
O2···C13vi3.310 (5)C14···H2ii3.0259
O3···C1vii3.181 (4)C14···H40v2.8729
O3···C5viii3.362 (5)C14···H16A2.9675
O3···C2vii3.254 (5)C15···H122.8331
O4···O2ix2.723 (4)H1···C82.7603
O1···H15Biii2.6716H1···C132.6246
O1···H92.5593H1···H132.3038
O1···H52.5112H1···O3vii2.5375
O1···H12iv2.3753H2···O3vii2.6865
O2···H4x2.7938H2···S1xii3.1915
O2···H15A2.5252H2···C14xii3.0259
O2···H40v1.9041H3···O3xiii2.7663
O3···H15A2.4992H4···O2xiii2.7938
O3···H5viii2.8039H5···O12.5112
O3···H3x2.7663H5···O3iv2.8039
O3···H1vii2.5375H5···C12iii3.0850
O3···H2vii2.6865H9···O12.5593
O3···H15B2.8289H12···C152.8331
O4···H16Bxi2.5851H12···H15B2.3136
C1···C133.122 (5)H12···O1viii2.3753
C1···O3vii3.181 (4)H13···C12.6917
C2···O3vii3.254 (5)H13···C62.8332
C2···C14xii3.449 (5)H13···H12.3038
C5···C17iv3.565 (6)H15A···O22.5252
C5···O3iv3.362 (5)H15A···O32.4992
C12···O1viii3.291 (4)H15B···O32.8289
C13···C14iii3.469 (5)H15B···C122.7730
C13···O2iii3.310 (5)H15B···H122.3136
C13···C13.122 (5)H15B···O1vi2.6716
C14···C13vi3.469 (5)H16A···C142.9675
C14···C2ii3.449 (5)H16A···C1ii2.8534
C15···O1vi3.236 (4)H16A···C2ii3.0609
C16···O23.414 (5)H16B···O4xi2.5851
C17···C5viii3.565 (6)H40···O2ix1.9041
C1···H132.6917H40···C14ix2.8728
C1···H16Axii2.8534
C10—S1—C1491.44 (16)N1—C15—C16112.2 (3)
C17—O4—H40109.44C15—C16—C17111.0 (3)
C11—N1—C15125.3 (3)O3—C17—C16124.4 (4)
C14—N1—C15118.5 (3)O4—C17—C16112.8 (3)
C11—N1—C14116.2 (3)O3—C17—O4122.8 (4)
C2—C1—C6120.2 (3)C2—C1—H1119.85
C1—C2—C3120.3 (4)C6—C1—H1119.92
C2—C3—C4120.8 (4)C1—C2—H2119.87
C3—C4—C5119.2 (3)C3—C2—H2119.83
C4—C5—C6120.7 (3)C2—C3—H3119.64
C1—C6—C5118.8 (3)C4—C3—H3119.60
C5—C6—C7118.3 (3)C3—C4—H4120.40
C1—C6—C7122.6 (3)C5—C4—H4120.36
O1—C7—C6119.1 (3)C4—C5—H5119.63
C6—C7—C8121.3 (2)C6—C5—H5119.69
O1—C7—C8119.5 (3)C8—C9—H9120.24
C7—C8—C9117.8 (2)C10—C9—H9120.15
C7—C8—C13123.4 (3)C11—C12—H12120.50
C9—C8—C13118.7 (3)C13—C12—H12120.41
C8—C9—C10119.6 (3)C8—C13—H13119.05
S1—C10—C9128.3 (2)C12—C13—H13119.03
C9—C10—C11120.4 (3)N1—C15—H15A109.14
S1—C10—C11111.3 (3)N1—C15—H15B109.20
N1—C11—C12127.6 (3)C16—C15—H15A109.13
C10—C11—C12120.2 (3)C16—C15—H15B109.19
N1—C11—C10112.2 (3)H15A—C15—H15B107.91
C11—C12—C13119.1 (3)C15—C16—H16A109.47
C8—C13—C12121.9 (3)C15—C16—H16B109.45
S1—C14—O2125.1 (3)C17—C16—H16A109.45
O2—C14—N1126.0 (3)C17—C16—H16B109.45
S1—C14—N1108.9 (2)H16A—C16—H16B108.01
C14—S1—C10—C9179.9 (3)C1—C6—C7—O1155.0 (3)
C14—S1—C10—C110.0 (2)C5—C6—C7—O119.6 (4)
C10—S1—C14—O2179.6 (3)C5—C6—C7—C8161.0 (3)
C10—S1—C14—N10.6 (2)O1—C7—C8—C929.1 (4)
C14—N1—C11—C101.3 (4)C6—C7—C8—C1332.6 (4)
C15—N1—C11—C121.6 (5)O1—C7—C8—C13148.0 (3)
C14—N1—C11—C12178.5 (3)C6—C7—C8—C9150.3 (3)
C15—N1—C11—C10178.5 (3)C7—C8—C9—C10178.2 (3)
C15—N1—C14—S1178.6 (2)C7—C8—C13—C12177.1 (3)
C15—N1—C14—O21.1 (5)C9—C8—C13—C120.1 (5)
C11—N1—C15—C1692.9 (4)C13—C8—C9—C101.0 (4)
C14—N1—C15—C1687.2 (4)C8—C9—C10—C110.6 (5)
C11—N1—C14—S11.2 (3)C8—C9—C10—S1179.6 (2)
C11—N1—C14—O2179.0 (3)C9—C10—C11—N1179.4 (3)
C6—C1—C2—C30.1 (5)S1—C10—C11—C12179.1 (2)
C2—C1—C6—C50.0 (5)S1—C10—C11—N10.7 (3)
C2—C1—C6—C7174.5 (3)C9—C10—C11—C120.7 (5)
C1—C2—C3—C40.2 (6)C10—C11—C12—C131.6 (5)
C2—C3—C4—C50.0 (6)N1—C11—C12—C13178.5 (3)
C3—C4—C5—C60.2 (6)C11—C12—C13—C81.3 (5)
C4—C5—C6—C10.2 (5)N1—C15—C16—C17166.1 (3)
C4—C5—C6—C7174.6 (3)C15—C16—C17—O4177.9 (3)
C1—C6—C7—C824.4 (4)C15—C16—C17—O30.7 (5)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1/2, z+1/2; (iii) x, y+1/2, z1/2; (iv) x, y1/2, z+1/2; (v) x+1, y1/2, z+3/2; (vi) x, y+1/2, z+1/2; (vii) x, y+1, z+1; (viii) x, y+1/2, z+1/2; (ix) x+1, y+1/2, z+3/2; (x) x+1, y, z+1; (xi) x+1, y+1, z+1; (xii) x1, y+1/2, z1/2; (xiii) x1, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H40···O2ix0.821.902.723 (4)176
C1—H1···O3vii0.932.543.181 (4)127
C12—H12···O1viii0.932.383.291 (4)168
C16—H16B···O4xi0.972.593.552 (6)175
Symmetry codes: (vii) x, y+1, z+1; (viii) x, y+1/2, z+1/2; (ix) x+1, y+1/2, z+3/2; (xi) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC17H13NO4S
Mr327.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.352 (5), 12.921 (5), 12.908 (5)
β (°) 104.370 (5)
V3)1511.0 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionPart of the refinement model (ΔF)
(Parkin et al., 1995); cubic fit to sin(θ)/λ - 24 parameters
Tmin, Tmax0.944, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
4283, 2818, 1906
Rint0.002
(sin θ/λ)max1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.190, 1.06
No. of reflections2818
No. of parameters208
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.34, 0.38

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
S1—C101.743 (4)O4—C171.330 (5)
S1—C141.781 (4)N1—C111.384 (5)
O1—C71.226 (4)N1—C151.471 (5)
O2—C141.213 (5)N1—C141.379 (5)
O3—C171.198 (5)
C10—S1—C1491.44 (16)N1—C11—C10112.2 (3)
C11—N1—C15125.3 (3)S1—C14—O2125.1 (3)
C14—N1—C15118.5 (3)O2—C14—N1126.0 (3)
C11—N1—C14116.2 (3)S1—C14—N1108.9 (2)
O1—C7—C6119.1 (3)N1—C15—C16112.2 (3)
O1—C7—C8119.5 (3)C15—C16—C17111.0 (3)
S1—C10—C9128.3 (2)O3—C17—C16124.4 (4)
S1—C10—C11111.3 (3)O4—C17—C16112.8 (3)
N1—C11—C12127.6 (3)O3—C17—O4122.8 (4)
C14—N1—C11—C101.3 (4)C5—C6—C7—O119.6 (4)
C15—N1—C14—O21.1 (5)O1—C7—C8—C929.1 (4)
C11—N1—C15—C1692.9 (4)O1—C7—C8—C13148.0 (3)
C14—N1—C15—C1687.2 (4)N1—C15—C16—C17166.1 (3)
C11—N1—C14—O2179.0 (3)C15—C16—C17—O4177.9 (3)
C1—C6—C7—O1155.0 (3)C15—C16—C17—O30.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H40···O2i0.821.902.723 (4)176
C1—H1···O3ii0.932.543.181 (4)127
C12—H12···O1iii0.932.383.291 (4)168
C16—H16B···O4iv0.972.593.552 (6)175
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+1, z+1; (iii) x, y+1/2, z+1/2; (iv) x+1, y+1, z+1.
 

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