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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3023
https://doi.org/10.1107/S1600536812036999

tert-Butyl N-{4-[N-(4-hy­dr­oxy­phen­yl)carbamo­yl]benz­yl}carbamate

Hai-Yang Yu,a Xin Fang,a* Ming-Dong Huangb and Jun-Dong Wanga

aCollege of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou 350108, People's Republic of China, and bFujian Institute of Research on the Structure of Matter, State Key Laboratory of Structural Chemistry, Chinese Academy of Sciences, Fuzhou 350002, People's Republic of China
*Correspondence e-mail: fangxin@fzu.edu.cn

(Received 25 August 2012; accepted 27 August 2012; online 26 September 2012)

In the title compound, C19H22N2O4, the dihedral angle between the aromatic rings is 67.33 (2)°. In the crystal, mol­ecules are linked through N—H⋯O and O—H⋯O hydrogen bonds, generating a two-dimensional network lying parallel to (100). As a result of the twist of the mol­ecular skeleton and the hindrance of the tert-butyl groups, no π–π inter­actions exist between the aromatic rings.

Related literature

For biochemical background, see: Jiang (2009[Jiang, L. G. (2009). Chin. J. Struct. Chem. pp. 253-259.]).

[Scheme 1]

Experimental

Crystal data

  • C19H22N2O4

  • Mr = 342.39

  • Monoclinic, P 21 /c

  • a = 12.289 (3) Å

  • b = 14.185 (3) Å

  • c = 10.980 (2) Å

  • β = 98.21 (3)°

  • V = 1894.4 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.66 × 0.66 × 0.47 mm
Data collection

  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: numerical (NUMABS; Higashi, 2000[Higashi, T. (2000). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.975, Tmax = 0.984

  • 15051 measured reflections

  • 4230 independent reflections

  • 3921 reflections with I > 2σ(I)

  • Rint = 0.028
Refinement

  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.166

  • S = 1.13

  • 4230 reflections

  • 278 parameters

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

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N1⋯O4i 0.88 (2) 2.10 (2) 2.949 (2) 160.6 (18)
N2—H2N2⋯O2ii 0.85 (2) 2.10 (2) 2.897 (2) 156.8 (19)
O4—H4O4⋯O3iii 0.87 (3) 1.78 (3) 2.6534 (18) 175 (3)
Symmetry codes: (i) x, y-1, z; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2007[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEX (McArdle, 1995[McArdle, P. (1995). J. Appl. Cryst. 28, 65.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812036999/hb6946sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036999/hb6946Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812036999/hb6946Isup3.cml

checkCIF report


Comment top

The title compound (I), (Fig. 1) is prepared as an intermediate of urokinase inhibitor (Jiang et al., 2009). The molecule is constructed by the main body of 4-(aminomethyl)benzylcarbonic, the N-protection group of tert-butyl oxycarbonyl, and the 4-aminophenol amidated the 4-(aminomethyl)benzylcarbonic acid. In the crystal, dihedral angle between the planes of N-protection carbamate (C4, C5, O1, O2, N1) and methylene benzene moieties is 80.66 (8)°, and between the benzene rings linked by amide bond is 67.33 (2)°. Strong hydrogen bonds, N1—H···O4, N2—H···O2, and O4—H···O3, exist in the crystal packing, as listed in table 1. By these hydrogen bonds, a two-dimensional supermolecular network paralleled with (100) plane was formed (Fig. 2). The network planes packed with weak van de Walss interactions (Fig. 3), where all tert-butyl moieties are in one side of the network plane and interacted with the tert-butyl moieties of the neighbor plane, and although the aromatic backbones are face to face packed, there are not π-π interactions between the aromatic rings because of the twist of the skeletons.

Related literature top

For biochemical background, see: Jiang (2009).

Experimental top

A solution of 4-(aminomethyl)benzoic acid (1.51 g, 10 mmol), triethylamine (3 ml), tetrahydrofuran (THF, 20 ml) and 20 ml of water was stirred and added dropwise a solution of Di-tert-butyl dicarbonate ((Boc)2O, 3. 27 g, 15 mmol) in 20 ml of THF under room temperature. After addition the solution was stirred furtherly overnight under room temperature. Then the solution was concentrated under vacuum to about 30 ml. 100 ml of 5% NaHCO3 solution was added to the solution then the solution was extracted with dichloromethane (30 ml × 3). The water layer was acidified by 3 N HCl until pH ≈ 4 then white precipitate appeared. The precipitate was filtrated, washed with water, and dried to get white solid of N-Boc protected 4-(aminomethyl)benzoic acid (BAMBZA), 2.39 g (yield: 95%).

A solution of BAMBZA (684 mg, 2 mmol), 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU, 1138 mg, 3 mmol), N,N-diisopropylethylamine (DIEA, 310 mg, 2.4 mmol) and 4-aminophenol in 15 ml of DMF was stirred overnight at room temperature. Then the solution was treated with 5% NaHCO3 solution (150 mL) and the precipitate was filtrated, washed with water, dried, and purification by column chromatography (dichloromethane/methanol, 50:1) to give white solid of tert-butyl 4-(4-hydroxyphenylcarbamoyl)benzylcarbamate, 551 mg (yield: 80%). The solid was dissolved again in DMF, and filtrated. The solution was evaporated slowly at room temperature for a week to yield colourless blocks.

Refinement top

H atoms on the tert-butyl moiety were placed at idealized positions of CH3 group and refined as riding atoms with Uiso(H) = 1.5 × Ueq(C). Other H atoms were located in a difference Fourier map and refined isotropically, with C—H distances in the range of 0.95 to 1.04 Å, N—H distances of 0.86 and 0.90 Å, and O—H distances of 0.88 Å.

Structure description top

The title compound (I), (Fig. 1) is prepared as an intermediate of urokinase inhibitor (Jiang et al., 2009). The molecule is constructed by the main body of 4-(aminomethyl)benzylcarbonic, the N-protection group of tert-butyl oxycarbonyl, and the 4-aminophenol amidated the 4-(aminomethyl)benzylcarbonic acid. In the crystal, dihedral angle between the planes of N-protection carbamate (C4, C5, O1, O2, N1) and methylene benzene moieties is 80.66 (8)°, and between the benzene rings linked by amide bond is 67.33 (2)°. Strong hydrogen bonds, N1—H···O4, N2—H···O2, and O4—H···O3, exist in the crystal packing, as listed in table 1. By these hydrogen bonds, a two-dimensional supermolecular network paralleled with (100) plane was formed (Fig. 2). The network planes packed with weak van de Walss interactions (Fig. 3), where all tert-butyl moieties are in one side of the network plane and interacted with the tert-butyl moieties of the neighbor plane, and although the aromatic backbones are face to face packed, there are not π-π interactions between the aromatic rings because of the twist of the skeletons.

For biochemical background, see: Jiang (2009).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The crystal structure of (I), drawn with 30% probability displacement ellipsoids. Hydrogen atoms are shown as spheres of arbitrary radii.
[Figure 2] Fig. 2. A supermolecular planar network formed by hydrogen bonds. Hydrogen atoms except those forming hydrogen bonds are omitted for clarity.
[Figure 3] Fig. 3. Packing of the planar networks. All hydrogen atoms are omitted for clarity.
tert-Butyl N-{4-[N-(4-hydroxyphenyl)carbamoyl]benzyl}carbamate top
Crystal data top
C19H22N2O4F(000) = 728
Mr = 342.39Dx = 1.200 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybcCell parameters from 5464 reflections
a = 12.289 (3) Åθ = 3.1–27.5°
b = 14.185 (3) ŵ = 0.09 mm−1
c = 10.980 (2) ÅT = 293 K
β = 98.21 (3)°Block, colourless
V = 1894.4 (7) Å30.66 × 0.66 × 0.47 mm
Z = 4
Data collection top
Rigaku Saturn724 CCD
diffractometer		4230 independent reflections
Radiation source: fine-focus sealed tube3921 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −15→15
Absorption correction: numerical
(NUMABS; Higashi, 2000)		k = −18→17
Tmin = 0.975, Tmax = 0.984l = −14→14
15051 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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0857P)2 + 0.2768P]
where P = (Fo2 + 2Fc2)/3
4230 reflections(Δ/σ)max < 0.001
278 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C19H22N2O4V = 1894.4 (7) Å3
Mr = 342.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.289 (3) ŵ = 0.09 mm−1
b = 14.185 (3) ÅT = 293 K
c = 10.980 (2) Å0.66 × 0.66 × 0.47 mm
β = 98.21 (3)°
Data collection top
Rigaku Saturn724 CCD
diffractometer		4230 independent reflections
Absorption correction: numerical
(NUMABS; Higashi, 2000)		3921 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.984Rint = 0.028
15051 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.15 e Å−3
4230 reflectionsΔρmin = −0.16 e Å−3
278 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*/Ueq
N10.23491 (12)0.02867 (9)0.32424 (14)0.0551 (3)
H1N10.2354 (16)−0.0024 (14)0.394 (2)0.066 (5)*
N20.18621 (12)0.52555 (9)0.44084 (12)0.0525 (3)
H2N20.2117 (16)0.4901 (14)0.5002 (19)0.064 (5)*
O10.39656 (9)−0.03555 (9)0.32021 (10)0.0611 (3)
O20.31884 (11)0.05183 (9)0.15710 (10)0.0663 (3)
O30.11660 (10)0.53752 (7)0.24078 (10)0.0561 (3)
O40.18329 (14)0.91196 (8)0.53081 (13)0.0774 (4)
H4O40.164 (2)0.9257 (19)0.602 (3)0.099 (8)*
C10.5584 (2)−0.1202 (3)0.3697 (3)0.1294 (12)
H1A0.5154−0.17480.38270.194*
H1B0.5715−0.08400.44430.194*
H1C0.6273−0.13950.34630.194*
C20.4655 (3)−0.1180 (3)0.1525 (3)0.1287 (12)
H2A0.4259−0.17320.17150.193*
H2B0.5310−0.13660.12040.193*
H2C0.4200−0.08090.09230.193*
C30.5595 (2)0.0279 (3)0.2484 (4)0.1448 (14)
H3A0.51870.06460.18400.217*
H3B0.62950.01130.22560.217*
H3C0.57040.06410.32300.217*
C40.49650 (16)−0.06027 (19)0.2683 (2)0.0810 (6)
C50.31757 (12)0.01781 (10)0.25879 (13)0.0492 (3)
C60.13695 (15)0.08113 (12)0.2755 (2)0.0630 (4)
H6A0.077 (2)0.0590 (17)0.321 (2)0.094 (7)*
H6B0.1167 (18)0.0648 (15)0.184 (2)0.077 (6)*
C70.14719 (12)0.18674 (10)0.28959 (14)0.0501 (3)
C80.09103 (14)0.24548 (12)0.20160 (15)0.0597 (4)
H80.0469 (17)0.2169 (14)0.129 (2)0.075 (6)*
C90.09462 (14)0.34193 (12)0.21584 (14)0.0568 (4)
H90.0569 (19)0.3852 (16)0.157 (2)0.086 (6)*
C100.15430 (11)0.38288 (10)0.31938 (12)0.0435 (3)
C110.21137 (15)0.32443 (11)0.40761 (15)0.0597 (4)
H110.2557 (17)0.3495 (15)0.481 (2)0.077 (6)*
C120.20749 (16)0.22745 (12)0.39187 (17)0.0649 (5)
H120.252 (2)0.1880 (19)0.452 (2)0.105 (8)*
C130.15207 (11)0.48764 (10)0.33042 (12)0.0435 (3)
C140.18580 (13)0.62478 (10)0.46470 (13)0.0482 (3)
C150.23604 (16)0.68721 (12)0.39467 (16)0.0615 (4)
H150.2717 (16)0.6622 (14)0.3276 (18)0.070 (5)*
C160.23500 (18)0.78243 (12)0.41852 (17)0.0667 (5)
H160.2678 (19)0.8254 (17)0.369 (2)0.090 (7)*
C170.18335 (14)0.81648 (11)0.51345 (14)0.0541 (4)
C180.13337 (14)0.75444 (11)0.58466 (14)0.0544 (4)
H180.0951 (15)0.7789 (13)0.6534 (18)0.066 (5)*
C190.13457 (14)0.65860 (11)0.55987 (13)0.0526 (4)
H190.1014 (16)0.6117 (14)0.6099 (18)0.069 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0620 (8)0.0446 (7)0.0592 (8)0.0042 (6)0.0101 (6)0.0020 (6)
N20.0736 (9)0.0402 (6)0.0427 (6)0.0055 (6)0.0048 (6)0.0025 (5)
O10.0551 (7)0.0719 (8)0.0553 (6)0.0085 (5)0.0043 (5)0.0100 (5)
O20.0732 (8)0.0750 (8)0.0482 (6)−0.0017 (6)−0.0002 (5)0.0098 (5)
O30.0659 (7)0.0519 (6)0.0486 (6)0.0052 (5)0.0010 (5)0.0109 (4)
O40.1278 (12)0.0449 (6)0.0667 (8)−0.0036 (7)0.0390 (8)−0.0084 (5)
C10.0897 (18)0.179 (3)0.114 (2)0.063 (2)−0.0057 (15)0.018 (2)
C20.1022 (19)0.180 (3)0.1023 (19)0.054 (2)0.0086 (15)−0.043 (2)
C30.0684 (16)0.175 (4)0.192 (4)−0.0281 (18)0.0242 (19)0.035 (3)
C40.0501 (10)0.1183 (18)0.0739 (12)0.0131 (10)0.0063 (9)0.0022 (11)
C50.0528 (8)0.0459 (7)0.0463 (7)−0.0058 (6)−0.0011 (6)−0.0013 (6)
C60.0528 (9)0.0475 (8)0.0860 (12)−0.0001 (7)0.0008 (9)−0.0128 (8)
C70.0453 (7)0.0466 (7)0.0575 (8)0.0026 (6)0.0035 (6)−0.0084 (6)
C80.0637 (10)0.0574 (9)0.0528 (8)−0.0003 (7)−0.0095 (7)−0.0097 (7)
C90.0647 (10)0.0551 (9)0.0462 (7)0.0040 (7)−0.0075 (7)0.0006 (6)
C100.0440 (7)0.0448 (7)0.0414 (6)0.0031 (5)0.0056 (5)−0.0008 (5)
C110.0732 (10)0.0465 (8)0.0521 (8)0.0073 (7)−0.0160 (7)−0.0048 (6)
C120.0785 (11)0.0458 (8)0.0619 (9)0.0102 (7)−0.0190 (8)−0.0026 (7)
C130.0440 (7)0.0445 (7)0.0425 (6)0.0024 (5)0.0078 (5)0.0039 (5)
C140.0588 (8)0.0416 (7)0.0433 (7)0.0037 (6)0.0042 (6)0.0011 (5)
C150.0806 (11)0.0503 (8)0.0590 (9)0.0008 (8)0.0284 (8)−0.0051 (7)
C160.0939 (13)0.0486 (9)0.0643 (10)−0.0069 (8)0.0347 (9)−0.0016 (7)
C170.0731 (10)0.0422 (7)0.0476 (7)−0.0011 (7)0.0116 (7)−0.0038 (6)
C180.0690 (10)0.0512 (8)0.0446 (7)0.0021 (7)0.0139 (7)−0.0039 (6)
C190.0653 (9)0.0484 (8)0.0451 (7)−0.0015 (7)0.0113 (6)0.0025 (6)
Geometric parameters (Å, º) top
N1—C51.334 (2)C6—C71.509 (2)
N1—C61.451 (2)C6—H6A1.00 (3)
N1—H1N10.88 (2)C6—H6B1.03 (2)
N2—C131.3380 (19)C7—C121.381 (2)
N2—C141.4318 (18)C7—C81.383 (2)
N2—H2N20.85 (2)C8—C91.377 (2)
O1—C51.3353 (18)C8—H80.99 (2)
O1—C41.468 (2)C9—C101.389 (2)
O2—C51.2185 (18)C9—H90.96 (2)
O3—C131.2397 (17)C10—C111.387 (2)
O4—C171.3677 (19)C10—C131.4914 (19)
O4—H4O40.87 (3)C11—C121.387 (2)
C1—C41.516 (3)C11—H110.97 (2)
C1—H1A0.9600C12—H120.97 (3)
C1—H1B0.9600C14—C151.376 (2)
C1—H1C0.9600C14—C191.381 (2)
C2—C41.515 (4)C15—C161.376 (2)
C2—H2A0.9600C15—H150.98 (2)
C2—H2B0.9600C16—C171.383 (2)
C2—H2C0.9600C16—H160.95 (2)
C3—C41.503 (4)C17—C181.379 (2)
C3—H3A0.9600C18—C191.387 (2)
C3—H3B0.9600C18—H181.006 (19)
C3—H3C0.9600C19—H190.99 (2)
C5—N1—C6121.07 (16)H6A—C6—H6B109.2 (19)
C5—N1—H1N1119.8 (13)C12—C7—C8118.19 (14)
C6—N1—H1N1118.6 (13)C12—C7—C6121.70 (15)
C13—N2—C14123.51 (12)C8—C7—C6120.03 (14)
C13—N2—H2N2119.5 (13)C9—C8—C7120.96 (14)
C14—N2—H2N2117.0 (13)C9—C8—H8120.3 (12)
C5—O1—C4121.84 (14)C7—C8—H8118.7 (12)
C17—O4—H4O4110.6 (17)C8—C9—C10120.87 (14)
C4—C1—H1A109.5C8—C9—H9123.7 (14)
C4—C1—H1B109.5C10—C9—H9115.4 (14)
H1A—C1—H1B109.5C11—C10—C9118.48 (14)
C4—C1—H1C109.5C11—C10—C13123.51 (12)
H1A—C1—H1C109.5C9—C10—C13118.00 (12)
H1B—C1—H1C109.5C10—C11—C12120.07 (14)
C4—C2—H2A109.5C10—C11—H11121.7 (12)
C4—C2—H2B109.5C12—C11—H11118.2 (12)
H2A—C2—H2B109.5C7—C12—C11121.42 (15)
C4—C2—H2C109.5C7—C12—H12119.6 (16)
H2A—C2—H2C109.5C11—C12—H12118.8 (16)
H2B—C2—H2C109.5O3—C13—N2121.28 (13)
C4—C3—H3A109.5O3—C13—C10120.84 (12)
C4—C3—H3B109.5N2—C13—C10117.85 (12)
H3A—C3—H3B109.5C15—C14—C19119.27 (14)
C4—C3—H3C109.5C15—C14—N2121.13 (14)
H3A—C3—H3C109.5C19—C14—N2119.60 (13)
H3B—C3—H3C109.5C14—C15—C16120.56 (15)
O1—C4—C3109.5 (2)C14—C15—H15118.3 (12)
O1—C4—C2109.32 (18)C16—C15—H15121.2 (12)
C3—C4—C2113.6 (3)C15—C16—C17120.27 (16)
O1—C4—C1102.04 (18)C15—C16—H16120.4 (14)
C3—C4—C1111.0 (3)C17—C16—H16119.3 (14)
C2—C4—C1110.7 (3)O4—C17—C18122.96 (14)
O2—C5—O1125.72 (15)O4—C17—C16117.42 (14)
O2—C5—N1123.93 (15)C18—C17—C16119.62 (14)
O1—C5—N1110.35 (13)C17—C18—C19119.76 (14)
N1—C6—C7114.75 (13)C17—C18—H18120.0 (11)
N1—C6—H6A106.6 (14)C19—C18—H18120.3 (11)
C7—C6—H6A108.5 (14)C14—C19—C18120.52 (14)
N1—C6—H6B108.5 (12)C14—C19—H19117.1 (11)
C7—C6—H6B109.2 (12)C18—C19—H19122.3 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O4i0.88 (2)2.10 (2)2.949 (2)160.6 (18)
N2—H2N2···O2ii0.85 (2)2.10 (2)2.897 (2)156.8 (19)
O4—H4O4···O3iii0.87 (3)1.78 (3)2.6534 (18)175 (3)
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H22N2O4
Mr342.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.289 (3), 14.185 (3), 10.980 (2)
β (°) 98.21 (3)
V (Å3)1894.4 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.66 × 0.66 × 0.47
Data collection
DiffractometerRigaku Saturn724 CCD
Absorption correctionNumerical
(NUMABS; Higashi, 2000)
Tmin, Tmax0.975, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		15051, 4230, 3921
Rint0.028
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.166, 1.13
No. of reflections4230
No. of parameters278
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.16

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), ORTEX (McArdle, 1995), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O4i0.88 (2)2.10 (2)2.949 (2)160.6 (18)
N2—H2N2···O2ii0.85 (2)2.10 (2)2.897 (2)156.8 (19)
O4—H4O4···O3iii0.87 (3)1.78 (3)2.6534 (18)175 (3)
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2.
 

Acknowledgements

This work was supported by the Foundations of Fuzhou University (2010-XQ-06), the Educational Department Foundations of Fujian Province (No. JA11020) and the NSFC (Nos. 31161130356 and 21171167).

References

First citationHigashi, T. (2000). NUMABS. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationJiang, L. G. (2009). Chin. J. Struct. Chem. pp. 253–259.  Google Scholar
 First citationMcArdle, P. (1995). J. Appl. Cryst. 28, 65.  CrossRef IUCr Journals Google Scholar
 First citationRigaku (2007). 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
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3023
https://doi.org/10.1107/S1600536812036999
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