organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-[2-Hydr­­oxy-4-(pyrrolidin-1-yl)benzo­yl]benzoic acid

aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
*Correspondence e-mail: yugp2005@yahoo.com.cn

(Received 24 March 2009; accepted 26 March 2009; online 31 March 2009)

The title compound, C18H17NO4, crystallizes with two indepen­dent mol­ecules in the asymmetric unit. The pyrrolidine ring in one mol­ecule is disordered over two positions, with refined site-occupancy factors of 0.853 (5) and 0.147 (5). The dihedral angles between the planes of the benzene rings in the two independent mol­ecules are 56.8 (2) and 68.2 (5)°. The mol­ecular conformations are stabilized by intra­molecular O—H⋯O hydrogen bonds. In the crystal structure, mol­ecules are linked by inter­molecular O—H⋯O hydrogen bonds, forming dimers and generating rings of graph-set motif R22(8).

Related literature

For the synthesis and applications of the title compound, see: Lee et al. (2005[Lee, L. G., Benson, S. C., Rosenblum, B. B., Spurgeon, S. L. & Graham, R. J. (2005). US Patent No. 0 112 781.]); Masakichi et al. (1974[Masakichi, Y., Shoichi, H., Takahuma, T. & Akio, K. (1974). German Patent No. DE2424935.]); Luo et al. (1994[Luo, H. P., Pan, J. L. & Lu, W. L. (1994). J. Zhejiang Univ. 28, 349-354.]). For bond-length and angle data for pyrrolidines, see: Effenberger et al. (1983[Effenberger, F., Agster, W., Fischer, P., Jogun, K. H., Stezowski, J. J., Daltrozzo, E. & Kollmannsberger-von Nell, G. (1983). J. Org. Chem. 48, 4649-4658.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17NO4

  • Mr = 311.33

  • Triclinic, [P \overline 1]

  • a = 10.841 (2) Å

  • b = 11.878 (2) Å

  • c = 13.781 (3) Å

  • α = 71.70 (3)°

  • β = 82.05 (3)°

  • γ = 65.17 (3)°

  • V = 1529.0 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 113 K

  • 0.18 × 0.16 × 0.12 mm

Data collection
  • Rigaku SATURN CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.983, Tmax = 0.989

  • 13535 measured reflections

  • 6888 independent reflections

  • 4673 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.136

  • S = 1.04

  • 6888 reflections

  • 437 parameters

  • 10 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2 0.956 (19) 1.66 (2) 2.547 (2) 151.8 (18)
O5—H5⋯O6 0.943 (19) 1.68 (2) 2.565 (2) 154.9 (19)
O7—H7A⋯O3i 0.86 (2) 1.784 (10) 2.6387 (17) 169.3 (19)
O4—H4⋯O8ii 0.879 (10) 1.785 (11) 2.6451 (19) 166 (2)
Symmetry codes: (i) x+1, y, z-1; (ii) x-1, y, z+1.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

2-[2-Hydroxy-4-(1-pyrrolidinyl)benzoyl)]benzoic acid is an intermediate in the synthesis of pyrrolidinylrhodamine (Lee et al., 2005) and its derivatives (Masakichi et al., 1974). It has been synthesized from 3-pyrrolidinylphenol and phthalic anhydride in toluene (Luo et al.,1994). Although its synthesis has been studied, the crystal structure of title compound has not been investigated. In this paper we reported its crystal structure.

The title compound crystallizes with two independent molecules in the asymmetric unit (Fig. 1). Bond lengths and angles within the pyrrolidine rings are normal and in good agreement with those reported previously for 2,4,6-tripyrrolidino-2',4',6'-trinitrobiphenyl (Effenberger et al., 1983). The dihedral angles between the planes of the benzene rings in the two independent molecules are 56.8 (2) and 68.2 (5)°. The molecular conformations are stabilized by intramolecular O—H···O hydrogen bonds (Table 1). In the crystal packing, the molecules are linked by intermolecular O—H···O hydrogen bonds to form dimers generating rings of graph-set motif R22(8) (Bernstein et al., 1995).

Related literature top

For the synthesis and applications of the title compound, see: Lee et al. (2005); Masakichi et al. (1974); Luo et al. (1994). For bond-length and angle data fo pyrrolidine, see: Effenberger et al. (1983). For details of hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A solution of 3-pyrrolidinylphenol (1.20 g, 7.36 mmol) and phthalic anhydride (1.31 g, 8.83 mmol) in toluene was refluxed under N2 for 3 h. The mixture was cooled to 50–60°C. Then 7 ml of 35.0% aqueous NaOH (w/w) was added and heated at 90° C for 6 h. The resulting mixture was poured into 70 ml of H2O, acidified with hydrochloric acid, and allowed to stand at room temperature for 2 h. The suspension was then filtered. The solid was recrystallized from a mixture of water and methanol, and then dried to afford the desired product (1.63 g, 70.7%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a CD3OD/CDCl3 (5:1 v/v) solution.

Refinement top

Hydroxy H atoms were found on a difference Fourier map and isotropically refined with Uiso(H) = 1.5 Ueq(O). All other H atoms were placed at calculated positions and refined using a riding model, with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2Ueq(C). The pyrrolidine group in one molecular was found to be disordered. Atoms C19, C20 and C21 were therefore refined over two positions with refined occupancies of 0.853 (5) and 0.147 (5) for primed and unprimed atoms, respectively.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 40% probability level.
2-[2-Hydroxy-4-(pyrrolidin-1-yl)benzoyl]benzoic acid top
Crystal data top
C18H17NO4Z = 4
Mr = 311.33F(000) = 656
Triclinic, P1Dx = 1.352 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.841 (2) ÅCell parameters from 4028 reflections
b = 11.878 (2) Åθ = 1.6–27.5°
c = 13.781 (3) ŵ = 0.10 mm1
α = 71.70 (3)°T = 113 K
β = 82.05 (3)°Block, colourless
γ = 65.17 (3)°0.18 × 0.16 × 0.12 mm
V = 1529.0 (7) Å3
Data collection top
Rigaku SATURN CCD area-detector
diffractometer
6888 independent reflections
Radiation source: rotating anode4673 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.036
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 1.6°
ω and ϕ scansh = 1410
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1513
Tmin = 0.983, Tmax = 0.989l = 1716
13535 measured reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0749P)2]
where P = (Fo2 + 2Fc2)/3
6888 reflections(Δ/σ)max < 0.001
437 parametersΔρmax = 0.33 e Å3
10 restraintsΔρmin = 0.25 e Å3
Crystal data top
C18H17NO4γ = 65.17 (3)°
Mr = 311.33V = 1529.0 (7) Å3
Triclinic, P1Z = 4
a = 10.841 (2) ÅMo Kα radiation
b = 11.878 (2) ŵ = 0.10 mm1
c = 13.781 (3) ÅT = 113 K
α = 71.70 (3)°0.18 × 0.16 × 0.12 mm
β = 82.05 (3)°
Data collection top
Rigaku SATURN CCD area-detector
diffractometer
6888 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
4673 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.989Rint = 0.036
13535 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04810 restraints
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.33 e Å3
6888 reflectionsΔρmin = 0.25 e Å3
437 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.45366 (12)0.59128 (10)1.11419 (8)0.0288 (3)
H10.443 (2)0.6119 (18)1.1774 (14)0.043*
O20.40164 (12)0.71748 (10)1.24448 (8)0.0294 (3)
O30.09923 (13)0.84631 (12)1.27107 (8)0.0348 (3)
O40.10829 (15)0.86955 (13)1.42445 (9)0.0429 (3)
H40.053 (2)0.829 (2)1.4387 (16)0.064*
O50.67090 (12)0.78113 (10)0.09493 (8)0.0318 (3)
H50.653 (2)0.8114 (19)0.1531 (15)0.048*
O60.66160 (12)0.79633 (10)0.27761 (8)0.0308 (3)
O70.93501 (12)0.72631 (11)0.34563 (8)0.0293 (3)
H7A0.9825 (18)0.7726 (17)0.3252 (14)0.044*
O80.94767 (13)0.74504 (12)0.49982 (8)0.0371 (3)
N10.34912 (15)0.82293 (12)0.76564 (9)0.0292 (3)
N20.90372 (15)0.36958 (13)0.03616 (10)0.0304 (3)
C10.3095 (2)0.94066 (17)0.67866 (12)0.0426 (5)
H1A0.34821.00030.68460.051*
H1B0.20940.98650.67330.051*
C20.3704 (3)0.88786 (19)0.58723 (14)0.0582 (6)
H2A0.31690.94460.52460.070*
H2B0.46580.87890.57460.070*
C30.3620 (2)0.75708 (18)0.62026 (13)0.0483 (5)
H3A0.42730.69930.58120.058*
H3B0.26920.76600.61070.058*
C40.3988 (2)0.70541 (15)0.73310 (12)0.0330 (4)
H4A0.35300.64780.77150.040*
H4B0.49820.65750.74250.040*
C50.34975 (16)0.82278 (15)0.86414 (11)0.0245 (3)
C60.29963 (17)0.94070 (14)0.89045 (11)0.0265 (3)
H60.26321.02090.83900.032*
C70.30356 (16)0.93921 (14)0.98950 (11)0.0243 (3)
H70.26931.01931.00530.029*
C80.35634 (16)0.82382 (14)1.06903 (11)0.0221 (3)
C90.40463 (16)0.70647 (14)1.04206 (11)0.0228 (3)
C100.40242 (16)0.70541 (14)0.94228 (11)0.0240 (3)
H100.43650.62540.92630.029*
C110.35830 (16)0.82146 (14)1.17426 (11)0.0236 (3)
C120.31291 (16)0.94406 (14)1.20471 (11)0.0240 (3)
C130.37622 (17)1.02936 (15)1.16136 (12)0.0275 (4)
H130.43821.01621.10600.033*
C140.34921 (18)1.13357 (15)1.19853 (13)0.0325 (4)
H140.39181.19191.16790.039*
C150.26080 (19)1.15270 (16)1.27972 (13)0.0349 (4)
H150.24421.22301.30580.042*
C160.19610 (18)1.06921 (15)1.32333 (12)0.0307 (4)
H160.13471.08291.37890.037*
C170.22088 (17)0.96580 (15)1.28596 (11)0.0254 (3)
C180.13923 (17)0.88714 (15)1.32972 (11)0.0264 (3)
C190.9822 (5)0.2294 (2)0.0686 (2)0.0342 (8)0.853 (5)
H19A0.94800.18900.13470.041*0.853 (5)
H19B1.07970.20850.07550.041*0.853 (5)
C200.9604 (2)0.1837 (2)0.01711 (17)0.0335 (6)0.853 (5)
H20A0.87890.16330.00390.040*0.853 (5)
H20B1.04060.10650.02580.040*0.853 (5)
C210.9410 (3)0.3008 (3)0.1104 (2)0.0376 (7)0.853 (5)
H21A1.03000.29860.14060.045*0.853 (5)
H21B0.88670.30160.16300.045*0.853 (5)
C19'0.967 (4)0.2271 (10)0.0567 (12)0.0342 (8)0.147 (5)
H19C0.90220.18710.08800.041*0.147 (5)
H19D1.04820.18710.10090.041*0.147 (5)
C20'1.0060 (14)0.2181 (13)0.0526 (10)0.0335 (6)0.147 (5)
H20C1.09500.22450.07030.040*0.147 (5)
H20D1.01660.13230.05560.040*0.147 (5)
C21'0.903 (2)0.3222 (14)0.1313 (13)0.0376 (7)0.147 (5)
H21C0.82610.30050.13770.045*0.147 (5)
H21D0.94370.34720.19910.045*0.147 (5)
C220.8662 (2)0.42004 (18)0.07185 (12)0.0351 (4)
H22A0.89650.48770.10710.042*0.853 (5)
H22B0.76970.45240.07970.042*0.853 (5)
H22C0.90830.47910.10540.042*0.147 (5)
H22D0.76960.46910.07610.042*0.147 (5)
C230.86444 (17)0.44414 (15)0.10045 (11)0.0257 (3)
C240.90176 (18)0.38879 (15)0.20557 (11)0.0286 (4)
H240.95810.29930.23010.034*
C250.85731 (17)0.46321 (14)0.27076 (11)0.0258 (3)
H250.88210.42380.34070.031*
C260.77521 (16)0.59747 (14)0.23827 (11)0.0235 (3)
C270.74369 (16)0.65237 (14)0.13248 (11)0.0244 (3)
C280.78626 (17)0.57779 (15)0.06598 (11)0.0269 (4)
H280.76250.61710.00410.032*
C290.72606 (16)0.67720 (14)0.30674 (11)0.0241 (3)
C300.74358 (16)0.61217 (14)0.42053 (11)0.0246 (3)
C310.67243 (18)0.53419 (16)0.46469 (12)0.0323 (4)
H310.62180.51960.42250.039*
C320.67458 (18)0.47761 (17)0.56943 (13)0.0354 (4)
H320.62590.42430.59850.043*
C330.74738 (18)0.49875 (16)0.63124 (12)0.0346 (4)
H330.74810.46080.70310.042*
C340.81990 (17)0.57562 (15)0.58857 (11)0.0296 (4)
H340.87010.58980.63150.036*
C350.81935 (17)0.63226 (14)0.48276 (11)0.0244 (3)
C360.90522 (16)0.70674 (14)0.43999 (11)0.0243 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0362 (7)0.0172 (5)0.0278 (6)0.0074 (5)0.0014 (5)0.0039 (4)
O20.0368 (7)0.0223 (6)0.0260 (5)0.0121 (5)0.0023 (5)0.0034 (4)
O30.0379 (8)0.0426 (7)0.0374 (6)0.0250 (6)0.0079 (5)0.0202 (5)
O40.0558 (10)0.0545 (9)0.0291 (6)0.0343 (7)0.0099 (6)0.0132 (6)
O50.0383 (8)0.0202 (6)0.0303 (6)0.0079 (5)0.0105 (5)0.0007 (4)
O60.0342 (7)0.0200 (6)0.0348 (6)0.0087 (5)0.0039 (5)0.0048 (5)
O70.0327 (7)0.0353 (7)0.0248 (5)0.0196 (6)0.0058 (5)0.0093 (5)
O80.0495 (9)0.0444 (7)0.0277 (6)0.0267 (7)0.0010 (5)0.0132 (5)
N10.0357 (9)0.0216 (7)0.0271 (7)0.0082 (6)0.0030 (6)0.0063 (5)
N20.0358 (9)0.0307 (7)0.0286 (7)0.0152 (7)0.0003 (6)0.0110 (6)
C10.0649 (15)0.0269 (9)0.0294 (8)0.0128 (9)0.0119 (8)0.0022 (7)
C20.095 (2)0.0420 (11)0.0305 (9)0.0216 (12)0.0078 (10)0.0060 (8)
C30.0655 (16)0.0352 (10)0.0351 (9)0.0070 (10)0.0115 (9)0.0118 (8)
C40.0399 (11)0.0242 (8)0.0322 (8)0.0077 (8)0.0037 (7)0.0101 (7)
C50.0217 (9)0.0231 (8)0.0283 (7)0.0090 (7)0.0019 (6)0.0075 (6)
C60.0286 (10)0.0176 (7)0.0288 (7)0.0073 (7)0.0022 (6)0.0026 (6)
C70.0235 (9)0.0189 (7)0.0296 (7)0.0082 (7)0.0026 (6)0.0074 (6)
C80.0196 (8)0.0195 (7)0.0272 (7)0.0095 (7)0.0022 (6)0.0052 (6)
C90.0202 (8)0.0166 (7)0.0283 (7)0.0070 (7)0.0021 (6)0.0035 (6)
C100.0247 (9)0.0179 (7)0.0287 (7)0.0086 (7)0.0023 (6)0.0066 (6)
C110.0206 (9)0.0200 (7)0.0287 (7)0.0094 (7)0.0027 (6)0.0044 (6)
C120.0248 (9)0.0215 (7)0.0260 (7)0.0092 (7)0.0048 (6)0.0054 (6)
C130.0243 (9)0.0237 (8)0.0329 (8)0.0095 (7)0.0033 (6)0.0051 (6)
C140.0311 (10)0.0237 (8)0.0435 (9)0.0127 (8)0.0080 (8)0.0049 (7)
C150.0391 (11)0.0268 (9)0.0429 (9)0.0118 (8)0.0093 (8)0.0135 (7)
C160.0323 (10)0.0287 (9)0.0306 (8)0.0085 (8)0.0029 (7)0.0117 (7)
C170.0271 (9)0.0241 (8)0.0248 (7)0.0095 (7)0.0043 (6)0.0058 (6)
C180.0279 (10)0.0258 (8)0.0241 (7)0.0083 (7)0.0008 (6)0.0092 (6)
C190.0311 (17)0.0329 (10)0.0428 (12)0.0115 (9)0.0008 (11)0.0178 (8)
C200.0252 (13)0.0373 (12)0.0430 (12)0.0120 (10)0.0024 (9)0.0196 (10)
C210.044 (2)0.0553 (15)0.0303 (14)0.0316 (14)0.0065 (11)0.0203 (13)
C19'0.0311 (17)0.0329 (10)0.0428 (12)0.0115 (9)0.0008 (11)0.0178 (8)
C20'0.0252 (13)0.0373 (12)0.0430 (12)0.0120 (10)0.0024 (9)0.0196 (10)
C21'0.044 (2)0.0553 (15)0.0303 (14)0.0316 (14)0.0065 (11)0.0203 (13)
C220.0419 (11)0.0465 (11)0.0282 (8)0.0277 (9)0.0029 (7)0.0130 (7)
C230.0269 (9)0.0277 (8)0.0269 (7)0.0165 (7)0.0010 (6)0.0066 (6)
C240.0295 (10)0.0215 (8)0.0295 (8)0.0074 (7)0.0027 (7)0.0032 (6)
C250.0276 (9)0.0224 (8)0.0238 (7)0.0095 (7)0.0026 (6)0.0016 (6)
C260.0238 (9)0.0211 (7)0.0253 (7)0.0111 (7)0.0031 (6)0.0019 (6)
C270.0237 (9)0.0210 (8)0.0279 (7)0.0120 (7)0.0049 (6)0.0001 (6)
C280.0298 (10)0.0289 (8)0.0234 (7)0.0156 (8)0.0035 (6)0.0027 (6)
C290.0216 (9)0.0226 (8)0.0283 (7)0.0115 (7)0.0010 (6)0.0035 (6)
C300.0243 (9)0.0181 (7)0.0262 (7)0.0052 (7)0.0015 (6)0.0046 (6)
C310.0313 (10)0.0297 (9)0.0340 (8)0.0141 (8)0.0016 (7)0.0048 (7)
C320.0302 (10)0.0326 (9)0.0367 (9)0.0140 (8)0.0072 (7)0.0022 (7)
C330.0329 (11)0.0312 (9)0.0255 (8)0.0073 (8)0.0050 (7)0.0007 (6)
C340.0279 (10)0.0282 (8)0.0265 (7)0.0061 (8)0.0009 (7)0.0073 (6)
C350.0245 (9)0.0195 (7)0.0244 (7)0.0053 (7)0.0033 (6)0.0062 (6)
C360.0238 (9)0.0209 (7)0.0240 (7)0.0046 (7)0.0011 (6)0.0078 (6)
Geometric parameters (Å, º) top
O1—C91.3506 (18)C15—H150.9500
O1—H10.956 (18)C16—C171.388 (2)
O2—C111.2531 (18)C16—H160.9500
O3—C181.2635 (18)C17—C181.488 (2)
O4—C181.2754 (18)C19—C201.528 (3)
O4—H40.879 (10)C19—H19A0.9900
O5—C271.3535 (18)C19—H19B0.9900
O5—H50.943 (19)C20—C211.529 (3)
O6—C291.2419 (18)C20—H20A0.9900
O7—C361.2675 (18)C20—H20B0.9900
O7—H7A0.86 (2)C21—C221.528 (3)
O8—C361.2708 (18)C21—H21A0.9900
N1—C51.3577 (19)C21—H21B0.9900
N1—C41.461 (2)C19'—C20'1.532 (10)
N1—C11.470 (2)C19'—H19C0.9900
N2—C231.350 (2)C19'—H19D0.9900
N2—C221.464 (2)C20'—C21'1.512 (9)
N2—C191.464 (3)C20'—H20C0.9900
N2—C19'1.481 (10)C20'—H20D0.9900
C1—C21.528 (3)C21'—C221.517 (9)
C1—H1A0.9900C21'—H21C0.9900
C1—H1B0.9900C21'—H21D0.9900
C2—C31.514 (3)C22—H22A0.9600
C2—H2A0.9900C22—H22B0.9600
C2—H2B0.9900C22—H22C0.9600
C3—C41.523 (2)C22—H22D0.9600
C3—H3A0.9900C23—C281.404 (2)
C3—H3B0.9900C23—C241.427 (2)
C4—H4A0.9900C24—C251.357 (2)
C4—H4B0.9900C24—H240.9500
C5—C101.410 (2)C25—C261.416 (2)
C5—C61.419 (2)C25—H250.9500
C6—C71.366 (2)C26—C271.422 (2)
C6—H60.9500C26—C291.439 (2)
C7—C81.407 (2)C27—C281.374 (2)
C7—H70.9500C28—H280.9500
C8—C91.419 (2)C29—C301.513 (2)
C8—C111.445 (2)C30—C311.393 (2)
C9—C101.383 (2)C30—C351.398 (2)
C10—H100.9500C31—C321.387 (2)
C11—C121.505 (2)C31—H310.9500
C12—C131.395 (2)C32—C331.378 (2)
C12—C171.404 (2)C32—H320.9500
C13—C141.390 (2)C33—C341.391 (2)
C13—H130.9500C33—H330.9500
C14—C151.379 (3)C34—C351.401 (2)
C14—H140.9500C34—H340.9500
C15—C161.389 (2)C35—C361.486 (2)
C9—O1—H1105.3 (12)C19—C20—H20B111.3
C18—O4—H4108.2 (14)C21—C20—H20B111.3
C27—O5—H5103.5 (12)H20A—C20—H20B109.2
C36—O7—H7A113.3 (12)C22—C21—C20106.09 (19)
C5—N1—C4123.71 (13)C22—C21—H21A110.5
C5—N1—C1123.89 (13)C20—C21—H21A110.5
C4—N1—C1112.20 (12)C22—C21—H21B110.5
C23—N2—C22123.22 (14)C20—C21—H21B110.5
C23—N2—C19123.37 (16)H21A—C21—H21B108.7
C22—N2—C19113.35 (16)N2—C19'—C20'99.6 (9)
C23—N2—C19'130.8 (7)N2—C19'—H19C111.9
C22—N2—C19'105.2 (8)C20'—C19'—H19C111.9
N1—C1—C2102.82 (14)N2—C19'—H19D111.9
N1—C1—H1A111.2C20'—C19'—H19D111.9
C2—C1—H1A111.2H19C—C19'—H19D109.6
N1—C1—H1B111.2C21'—C20'—C19'113.5 (14)
C2—C1—H1B111.2C21'—C20'—H20C108.9
H1A—C1—H1B109.1C19'—C20'—H20C108.9
C3—C2—C1102.90 (16)C21'—C20'—H20D108.9
C3—C2—H2A111.2C19'—C20'—H20D108.9
C1—C2—H2A111.2H20C—C20'—H20D107.7
C3—C2—H2B111.2C20'—C21'—C2292.4 (8)
C1—C2—H2B111.2C20'—C21'—H21C113.2
H2A—C2—H2B109.1C22—C21'—H21C113.2
C2—C3—C4103.74 (14)C20'—C21'—H21D113.2
C2—C3—H3A111.0C22—C21'—H21D113.2
C4—C3—H3A111.0H21C—C21'—H21D110.6
C2—C3—H3B111.0N2—C22—C21'117.1 (6)
C4—C3—H3B111.0N2—C22—C21102.47 (16)
H3A—C3—H3B109.0N2—C22—H22A111.2
N1—C4—C3103.05 (13)C21'—C22—H22A111.1
N1—C4—H4A111.2C21—C22—H22A111.3
C3—C4—H4A111.2N2—C22—H22B111.3
N1—C4—H4B111.2C21'—C22—H22B95.7
C3—C4—H4B111.2C21—C22—H22B111.3
H4A—C4—H4B109.1H22A—C22—H22B109.2
N1—C5—C10120.69 (14)N2—C22—H22C108.0
N1—C5—C6120.76 (14)C21'—C22—H22C108.0
C10—C5—C6118.54 (14)C21—C22—H22C106.1
C7—C6—C5120.17 (14)H22B—C22—H22C116.6
C7—C6—H6119.9N2—C22—H22D108.0
C5—C6—H6119.9C21'—C22—H22D108.0
C6—C7—C8122.66 (14)C21—C22—H22D124.1
C6—C7—H7118.7H22A—C22—H22D99.8
C8—C7—H7118.7H22C—C22—H22D107.3
C7—C8—C9116.69 (13)N2—C23—C28121.15 (14)
C7—C8—C11122.95 (14)N2—C23—C24120.63 (15)
C9—C8—C11120.32 (13)C28—C23—C24118.22 (14)
O1—C9—C10117.73 (13)C25—C24—C23120.37 (15)
O1—C9—C8120.52 (13)C25—C24—H24119.8
C10—C9—C8121.75 (14)C23—C24—H24119.8
C9—C10—C5120.19 (14)C24—C25—C26122.33 (14)
C9—C10—H10119.9C24—C25—H25118.8
C5—C10—H10119.9C26—C25—H25118.8
O2—C11—C8121.94 (14)C25—C26—C27116.66 (14)
O2—C11—C12116.45 (13)C25—C26—C29122.93 (13)
C8—C11—C12121.58 (13)C27—C26—C29120.41 (14)
C13—C12—C17118.87 (14)O5—C27—C28118.40 (13)
C13—C12—C11119.66 (15)O5—C27—C26120.04 (14)
C17—C12—C11120.91 (13)C28—C27—C26121.56 (14)
C14—C13—C12120.46 (16)C27—C28—C23120.77 (13)
C14—C13—H13119.8C27—C28—H28119.6
C12—C13—H13119.8C23—C28—H28119.6
C15—C14—C13120.30 (16)O6—C29—C26123.17 (13)
C15—C14—H14119.9O6—C29—C30118.04 (14)
C13—C14—H14119.9C26—C29—C30118.60 (13)
C14—C15—C16119.98 (15)C31—C30—C35119.40 (14)
C14—C15—H15120.0C31—C30—C29116.62 (14)
C16—C15—H15120.0C35—C30—C29123.87 (13)
C17—C16—C15120.23 (16)C32—C31—C30120.88 (16)
C17—C16—H16119.9C32—C31—H31119.6
C15—C16—H16119.9C30—C31—H31119.6
C16—C17—C12120.14 (15)C33—C32—C31119.93 (16)
C16—C17—C18117.52 (15)C33—C32—H32120.0
C12—C17—C18122.18 (13)C31—C32—H32120.0
O3—C18—O4123.47 (15)C32—C33—C34120.08 (15)
O3—C18—C17118.89 (13)C32—C33—H33120.0
O4—C18—C17117.57 (13)C34—C33—H33120.0
N2—C19—C20103.8 (2)C33—C34—C35120.42 (15)
N2—C19—H19A111.0C33—C34—H34119.8
C20—C19—H19A111.0C35—C34—H34119.8
N2—C19—H19B111.0C30—C35—C34119.28 (14)
C20—C19—H19B111.0C30—C35—C36122.17 (13)
H19A—C19—H19B109.0C34—C35—C36118.49 (14)
C19—C20—C21102.5 (2)O7—C36—O8123.24 (15)
C19—C20—H20A111.3O7—C36—C35118.03 (13)
C21—C20—H20A111.3O8—C36—C35118.71 (13)
C5—N1—C1—C2161.65 (17)N2—C19'—C20'—C21'37 (3)
C4—N1—C1—C213.4 (2)C19'—C20'—C21'—C2233 (2)
N1—C1—C2—C332.2 (2)C23—N2—C22—C21'172.6 (10)
C1—C2—C3—C439.5 (2)C19—N2—C22—C21'4.6 (10)
C5—N1—C4—C3174.12 (16)C19'—N2—C22—C21'1.7 (18)
C1—N1—C4—C310.8 (2)C23—N2—C22—C21177.07 (18)
C2—C3—C4—N131.0 (2)C19—N2—C22—C215.8 (3)
C4—N1—C5—C101.2 (2)C19'—N2—C22—C2112.1 (15)
C1—N1—C5—C10173.29 (16)C20'—C21'—C22—N218.3 (17)
C4—N1—C5—C6179.87 (16)C20'—C21'—C22—C2117 (2)
C1—N1—C5—C65.6 (3)C20—C21—C22—N225.2 (2)
N1—C5—C6—C7178.58 (15)C20—C21—C22—C21'123 (3)
C10—C5—C6—C70.3 (2)C22—N2—C23—C281.5 (2)
C5—C6—C7—C80.1 (2)C19—N2—C23—C28178.4 (3)
C6—C7—C8—C90.9 (2)C19'—N2—C23—C28170 (2)
C6—C7—C8—C11178.70 (15)C22—N2—C23—C24178.59 (15)
C7—C8—C9—O1178.27 (13)C19—N2—C23—C241.7 (3)
C11—C8—C9—O10.4 (2)C19'—N2—C23—C2410 (2)
C7—C8—C9—C101.2 (2)N2—C23—C24—C25177.27 (15)
C11—C8—C9—C10179.11 (14)C28—C23—C24—C252.8 (2)
O1—C9—C10—C5178.70 (14)C23—C24—C25—C261.1 (2)
C8—C9—C10—C50.8 (2)C24—C25—C26—C271.5 (2)
N1—C5—C10—C9178.92 (14)C24—C25—C26—C29179.25 (15)
C6—C5—C10—C90.0 (2)C25—C26—C27—O5177.00 (14)
C7—C8—C11—O2177.58 (14)C29—C26—C27—O52.2 (2)
C9—C8—C11—O20.2 (2)C25—C26—C27—C282.5 (2)
C7—C8—C11—C124.7 (2)C29—C26—C27—C28178.22 (14)
C9—C8—C11—C12177.58 (14)O5—C27—C28—C23178.68 (14)
O2—C11—C12—C13120.26 (16)C26—C27—C28—C230.9 (2)
C8—C11—C12—C1357.6 (2)N2—C23—C28—C27178.27 (14)
O2—C11—C12—C1751.0 (2)C24—C23—C28—C271.8 (2)
C8—C11—C12—C17131.09 (16)C25—C26—C29—O6175.12 (15)
C17—C12—C13—C140.4 (2)C27—C26—C29—O64.1 (2)
C11—C12—C13—C14171.03 (14)C25—C26—C29—C3010.0 (2)
C12—C13—C14—C150.9 (2)C27—C26—C29—C30170.85 (14)
C13—C14—C15—C161.4 (3)O6—C29—C30—C31110.01 (17)
C14—C15—C16—C170.5 (2)C26—C29—C30—C3165.2 (2)
C15—C16—C17—C120.8 (2)O6—C29—C30—C3566.1 (2)
C15—C16—C17—C18174.64 (15)C26—C29—C30—C35118.69 (17)
C13—C12—C17—C161.3 (2)C35—C30—C31—C320.7 (2)
C11—C12—C17—C16170.06 (14)C29—C30—C31—C32175.58 (15)
C13—C12—C17—C18173.97 (14)C30—C31—C32—C330.3 (3)
C11—C12—C17—C1814.7 (2)C31—C32—C33—C340.7 (3)
C16—C17—C18—O3141.35 (16)C32—C33—C34—C350.1 (3)
C12—C17—C18—O334.0 (2)C31—C30—C35—C341.3 (2)
C16—C17—C18—O435.6 (2)C29—C30—C35—C34174.75 (15)
C12—C17—C18—O4149.04 (16)C31—C30—C35—C36175.67 (15)
C23—N2—C19—C20161.5 (2)C29—C30—C35—C368.3 (2)
C22—N2—C19—C2015.6 (4)C33—C34—C35—C300.9 (2)
C19'—N2—C19—C2022 (7)C33—C34—C35—C36176.20 (15)
N2—C19—C20—C2130.0 (4)C30—C35—C36—O716.5 (2)
C19—C20—C21—C2234.7 (3)C34—C35—C36—O7160.48 (15)
C23—N2—C19'—C20'169.3 (7)C30—C35—C36—O8165.09 (15)
C22—N2—C19'—C20'21 (2)C34—C35—C36—O817.9 (2)
C19—N2—C19'—C20'124 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.956 (19)1.66 (2)2.547 (2)151.8 (18)
O5—H5···O60.943 (19)1.68 (2)2.565 (2)154.9 (19)
O7—H7A···O3i0.86 (2)1.78 (1)2.6387 (17)169 (2)
O4—H4···O8ii0.88 (1)1.79 (1)2.6451 (19)166 (2)
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z+1.

Experimental details

Crystal data
Chemical formulaC18H17NO4
Mr311.33
Crystal system, space groupTriclinic, P1
Temperature (K)113
a, b, c (Å)10.841 (2), 11.878 (2), 13.781 (3)
α, β, γ (°)71.70 (3), 82.05 (3), 65.17 (3)
V3)1529.0 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.18 × 0.16 × 0.12
Data collection
DiffractometerRigaku SATURN CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.983, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
13535, 6888, 4673
Rint0.036
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.136, 1.04
No. of reflections6888
No. of parameters437
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.25

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.956 (19)1.66 (2)2.547 (2)151.8 (18)
O5—H5···O60.943 (19)1.68 (2)2.565 (2)154.9 (19)
O7—H7A···O3i0.86 (2)1.784 (10)2.6387 (17)169.3 (19)
O4—H4···O8ii0.879 (10)1.785 (11)2.6451 (19)166 (2)
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z+1.
 

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationEffenberger, F., Agster, W., Fischer, P., Jogun, K. H., Stezowski, J. J., Daltrozzo, E. & Kollmannsberger-von Nell, G. (1983). J. Org. Chem. 48, 4649–4658.  CSD CrossRef CAS Web of Science Google Scholar
First citationLee, L. G., Benson, S. C., Rosenblum, B. B., Spurgeon, S. L. & Graham, R. J. (2005). US Patent No. 0 112 781.  Google Scholar
First citationLuo, H. P., Pan, J. L. & Lu, W. L. (1994). J. Zhejiang Univ. 28, 349–354.  CAS Google Scholar
First citationMasakichi, Y., Shoichi, H., Takahuma, T. & Akio, K. (1974). German Patent No. DE2424935.  Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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