organic compounds
tert-Butyl N-{4-[N-(4-hydroxyphenyl)carbamoyl]benzyl}carbamate
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
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.
Experimental
Crystal data
|
Refinement
|
Data collection: CrystalClear (Rigaku, 2007); cell CrystalClear; data reduction: CrystalClear; 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 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812036999/hb6946sup1.cif
contains datablocks I, global. DOI: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
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
(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.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.
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).
Data collection: CrystalClear (Rigaku, 2007); cell
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).C19H22N2O4 | F(000) = 728 |
Mr = 342.39 | Dx = 1.200 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -p 2ybc | Cell parameters from 5464 reflections |
a = 12.289 (3) Å | θ = 3.1–27.5° |
b = 14.185 (3) Å | µ = 0.09 mm−1 |
c = 10.980 (2) Å | T = 293 K |
β = 98.21 (3)° | Block, colourless |
V = 1894.4 (7) Å3 | 0.66 × 0.66 × 0.47 mm |
Z = 4 |
Rigaku Saturn724 CCD diffractometer | 4230 independent reflections |
Radiation source: fine-focus sealed tube | 3921 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 28.5714 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −15→15 |
Absorption correction: numerical (NUMABS; Higashi, 2000) | k = −18→17 |
Tmin = 0.975, Tmax = 0.984 | l = −14→14 |
15051 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H 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 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C19H22N2O4 | V = 1894.4 (7) Å3 |
Mr = 342.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.289 (3) Å | µ = 0.09 mm−1 |
b = 14.185 (3) Å | T = 293 K |
c = 10.980 (2) Å | 0.66 × 0.66 × 0.47 mm |
β = 98.21 (3)° |
Rigaku Saturn724 CCD diffractometer | 4230 independent reflections |
Absorption correction: numerical (NUMABS; Higashi, 2000) | 3921 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.984 | Rint = 0.028 |
15051 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.166 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | Δρmax = 0.15 e Å−3 |
4230 reflections | Δρmin = −0.16 e Å−3 |
278 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.23491 (12) | 0.02867 (9) | 0.32424 (14) | 0.0551 (3) | |
H1N1 | 0.2354 (16) | −0.0024 (14) | 0.394 (2) | 0.066 (5)* | |
N2 | 0.18621 (12) | 0.52555 (9) | 0.44084 (12) | 0.0525 (3) | |
H2N2 | 0.2117 (16) | 0.4901 (14) | 0.5002 (19) | 0.064 (5)* | |
O1 | 0.39656 (9) | −0.03555 (9) | 0.32021 (10) | 0.0611 (3) | |
O2 | 0.31884 (11) | 0.05183 (9) | 0.15710 (10) | 0.0663 (3) | |
O3 | 0.11660 (10) | 0.53752 (7) | 0.24078 (10) | 0.0561 (3) | |
O4 | 0.18329 (14) | 0.91196 (8) | 0.53081 (13) | 0.0774 (4) | |
H4O4 | 0.164 (2) | 0.9257 (19) | 0.602 (3) | 0.099 (8)* | |
C1 | 0.5584 (2) | −0.1202 (3) | 0.3697 (3) | 0.1294 (12) | |
H1A | 0.5154 | −0.1748 | 0.3827 | 0.194* | |
H1B | 0.5715 | −0.0840 | 0.4443 | 0.194* | |
H1C | 0.6273 | −0.1395 | 0.3463 | 0.194* | |
C2 | 0.4655 (3) | −0.1180 (3) | 0.1525 (3) | 0.1287 (12) | |
H2A | 0.4259 | −0.1732 | 0.1715 | 0.193* | |
H2B | 0.5310 | −0.1366 | 0.1204 | 0.193* | |
H2C | 0.4200 | −0.0809 | 0.0923 | 0.193* | |
C3 | 0.5595 (2) | 0.0279 (3) | 0.2484 (4) | 0.1448 (14) | |
H3A | 0.5187 | 0.0646 | 0.1840 | 0.217* | |
H3B | 0.6295 | 0.0113 | 0.2256 | 0.217* | |
H3C | 0.5704 | 0.0641 | 0.3230 | 0.217* | |
C4 | 0.49650 (16) | −0.06027 (19) | 0.2683 (2) | 0.0810 (6) | |
C5 | 0.31757 (12) | 0.01781 (10) | 0.25879 (13) | 0.0492 (3) | |
C6 | 0.13695 (15) | 0.08113 (12) | 0.2755 (2) | 0.0630 (4) | |
H6A | 0.077 (2) | 0.0590 (17) | 0.321 (2) | 0.094 (7)* | |
H6B | 0.1167 (18) | 0.0648 (15) | 0.184 (2) | 0.077 (6)* | |
C7 | 0.14719 (12) | 0.18674 (10) | 0.28959 (14) | 0.0501 (3) | |
C8 | 0.09103 (14) | 0.24548 (12) | 0.20160 (15) | 0.0597 (4) | |
H8 | 0.0469 (17) | 0.2169 (14) | 0.129 (2) | 0.075 (6)* | |
C9 | 0.09462 (14) | 0.34193 (12) | 0.21584 (14) | 0.0568 (4) | |
H9 | 0.0569 (19) | 0.3852 (16) | 0.157 (2) | 0.086 (6)* | |
C10 | 0.15430 (11) | 0.38288 (10) | 0.31938 (12) | 0.0435 (3) | |
C11 | 0.21137 (15) | 0.32443 (11) | 0.40761 (15) | 0.0597 (4) | |
H11 | 0.2557 (17) | 0.3495 (15) | 0.481 (2) | 0.077 (6)* | |
C12 | 0.20749 (16) | 0.22745 (12) | 0.39187 (17) | 0.0649 (5) | |
H12 | 0.252 (2) | 0.1880 (19) | 0.452 (2) | 0.105 (8)* | |
C13 | 0.15207 (11) | 0.48764 (10) | 0.33042 (12) | 0.0435 (3) | |
C14 | 0.18580 (13) | 0.62478 (10) | 0.46470 (13) | 0.0482 (3) | |
C15 | 0.23604 (16) | 0.68721 (12) | 0.39467 (16) | 0.0615 (4) | |
H15 | 0.2717 (16) | 0.6622 (14) | 0.3276 (18) | 0.070 (5)* | |
C16 | 0.23500 (18) | 0.78243 (12) | 0.41852 (17) | 0.0667 (5) | |
H16 | 0.2678 (19) | 0.8254 (17) | 0.369 (2) | 0.090 (7)* | |
C17 | 0.18335 (14) | 0.81648 (11) | 0.51345 (14) | 0.0541 (4) | |
C18 | 0.13337 (14) | 0.75444 (11) | 0.58466 (14) | 0.0544 (4) | |
H18 | 0.0951 (15) | 0.7789 (13) | 0.6534 (18) | 0.066 (5)* | |
C19 | 0.13457 (14) | 0.65860 (11) | 0.55987 (13) | 0.0526 (4) | |
H19 | 0.1014 (16) | 0.6117 (14) | 0.6099 (18) | 0.069 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0620 (8) | 0.0446 (7) | 0.0592 (8) | 0.0042 (6) | 0.0101 (6) | 0.0020 (6) |
N2 | 0.0736 (9) | 0.0402 (6) | 0.0427 (6) | 0.0055 (6) | 0.0048 (6) | 0.0025 (5) |
O1 | 0.0551 (7) | 0.0719 (8) | 0.0553 (6) | 0.0085 (5) | 0.0043 (5) | 0.0100 (5) |
O2 | 0.0732 (8) | 0.0750 (8) | 0.0482 (6) | −0.0017 (6) | −0.0002 (5) | 0.0098 (5) |
O3 | 0.0659 (7) | 0.0519 (6) | 0.0486 (6) | 0.0052 (5) | 0.0010 (5) | 0.0109 (4) |
O4 | 0.1278 (12) | 0.0449 (6) | 0.0667 (8) | −0.0036 (7) | 0.0390 (8) | −0.0084 (5) |
C1 | 0.0897 (18) | 0.179 (3) | 0.114 (2) | 0.063 (2) | −0.0057 (15) | 0.018 (2) |
C2 | 0.1022 (19) | 0.180 (3) | 0.1023 (19) | 0.054 (2) | 0.0086 (15) | −0.043 (2) |
C3 | 0.0684 (16) | 0.175 (4) | 0.192 (4) | −0.0281 (18) | 0.0242 (19) | 0.035 (3) |
C4 | 0.0501 (10) | 0.1183 (18) | 0.0739 (12) | 0.0131 (10) | 0.0063 (9) | 0.0022 (11) |
C5 | 0.0528 (8) | 0.0459 (7) | 0.0463 (7) | −0.0058 (6) | −0.0011 (6) | −0.0013 (6) |
C6 | 0.0528 (9) | 0.0475 (8) | 0.0860 (12) | −0.0001 (7) | 0.0008 (9) | −0.0128 (8) |
C7 | 0.0453 (7) | 0.0466 (7) | 0.0575 (8) | 0.0026 (6) | 0.0035 (6) | −0.0084 (6) |
C8 | 0.0637 (10) | 0.0574 (9) | 0.0528 (8) | −0.0003 (7) | −0.0095 (7) | −0.0097 (7) |
C9 | 0.0647 (10) | 0.0551 (9) | 0.0462 (7) | 0.0040 (7) | −0.0075 (7) | 0.0006 (6) |
C10 | 0.0440 (7) | 0.0448 (7) | 0.0414 (6) | 0.0031 (5) | 0.0056 (5) | −0.0008 (5) |
C11 | 0.0732 (10) | 0.0465 (8) | 0.0521 (8) | 0.0073 (7) | −0.0160 (7) | −0.0048 (6) |
C12 | 0.0785 (11) | 0.0458 (8) | 0.0619 (9) | 0.0102 (7) | −0.0190 (8) | −0.0026 (7) |
C13 | 0.0440 (7) | 0.0445 (7) | 0.0425 (6) | 0.0024 (5) | 0.0078 (5) | 0.0039 (5) |
C14 | 0.0588 (8) | 0.0416 (7) | 0.0433 (7) | 0.0037 (6) | 0.0042 (6) | 0.0011 (5) |
C15 | 0.0806 (11) | 0.0503 (8) | 0.0590 (9) | 0.0008 (8) | 0.0284 (8) | −0.0051 (7) |
C16 | 0.0939 (13) | 0.0486 (9) | 0.0643 (10) | −0.0069 (8) | 0.0347 (9) | −0.0016 (7) |
C17 | 0.0731 (10) | 0.0422 (7) | 0.0476 (7) | −0.0011 (7) | 0.0116 (7) | −0.0038 (6) |
C18 | 0.0690 (10) | 0.0512 (8) | 0.0446 (7) | 0.0021 (7) | 0.0139 (7) | −0.0039 (6) |
C19 | 0.0653 (9) | 0.0484 (8) | 0.0451 (7) | −0.0015 (7) | 0.0113 (6) | 0.0025 (6) |
N1—C5 | 1.334 (2) | C6—C7 | 1.509 (2) |
N1—C6 | 1.451 (2) | C6—H6A | 1.00 (3) |
N1—H1N1 | 0.88 (2) | C6—H6B | 1.03 (2) |
N2—C13 | 1.3380 (19) | C7—C12 | 1.381 (2) |
N2—C14 | 1.4318 (18) | C7—C8 | 1.383 (2) |
N2—H2N2 | 0.85 (2) | C8—C9 | 1.377 (2) |
O1—C5 | 1.3353 (18) | C8—H8 | 0.99 (2) |
O1—C4 | 1.468 (2) | C9—C10 | 1.389 (2) |
O2—C5 | 1.2185 (18) | C9—H9 | 0.96 (2) |
O3—C13 | 1.2397 (17) | C10—C11 | 1.387 (2) |
O4—C17 | 1.3677 (19) | C10—C13 | 1.4914 (19) |
O4—H4O4 | 0.87 (3) | C11—C12 | 1.387 (2) |
C1—C4 | 1.516 (3) | C11—H11 | 0.97 (2) |
C1—H1A | 0.9600 | C12—H12 | 0.97 (3) |
C1—H1B | 0.9600 | C14—C15 | 1.376 (2) |
C1—H1C | 0.9600 | C14—C19 | 1.381 (2) |
C2—C4 | 1.515 (4) | C15—C16 | 1.376 (2) |
C2—H2A | 0.9600 | C15—H15 | 0.98 (2) |
C2—H2B | 0.9600 | C16—C17 | 1.383 (2) |
C2—H2C | 0.9600 | C16—H16 | 0.95 (2) |
C3—C4 | 1.503 (4) | C17—C18 | 1.379 (2) |
C3—H3A | 0.9600 | C18—C19 | 1.387 (2) |
C3—H3B | 0.9600 | C18—H18 | 1.006 (19) |
C3—H3C | 0.9600 | C19—H19 | 0.99 (2) |
C5—N1—C6 | 121.07 (16) | H6A—C6—H6B | 109.2 (19) |
C5—N1—H1N1 | 119.8 (13) | C12—C7—C8 | 118.19 (14) |
C6—N1—H1N1 | 118.6 (13) | C12—C7—C6 | 121.70 (15) |
C13—N2—C14 | 123.51 (12) | C8—C7—C6 | 120.03 (14) |
C13—N2—H2N2 | 119.5 (13) | C9—C8—C7 | 120.96 (14) |
C14—N2—H2N2 | 117.0 (13) | C9—C8—H8 | 120.3 (12) |
C5—O1—C4 | 121.84 (14) | C7—C8—H8 | 118.7 (12) |
C17—O4—H4O4 | 110.6 (17) | C8—C9—C10 | 120.87 (14) |
C4—C1—H1A | 109.5 | C8—C9—H9 | 123.7 (14) |
C4—C1—H1B | 109.5 | C10—C9—H9 | 115.4 (14) |
H1A—C1—H1B | 109.5 | C11—C10—C9 | 118.48 (14) |
C4—C1—H1C | 109.5 | C11—C10—C13 | 123.51 (12) |
H1A—C1—H1C | 109.5 | C9—C10—C13 | 118.00 (12) |
H1B—C1—H1C | 109.5 | C10—C11—C12 | 120.07 (14) |
C4—C2—H2A | 109.5 | C10—C11—H11 | 121.7 (12) |
C4—C2—H2B | 109.5 | C12—C11—H11 | 118.2 (12) |
H2A—C2—H2B | 109.5 | C7—C12—C11 | 121.42 (15) |
C4—C2—H2C | 109.5 | C7—C12—H12 | 119.6 (16) |
H2A—C2—H2C | 109.5 | C11—C12—H12 | 118.8 (16) |
H2B—C2—H2C | 109.5 | O3—C13—N2 | 121.28 (13) |
C4—C3—H3A | 109.5 | O3—C13—C10 | 120.84 (12) |
C4—C3—H3B | 109.5 | N2—C13—C10 | 117.85 (12) |
H3A—C3—H3B | 109.5 | C15—C14—C19 | 119.27 (14) |
C4—C3—H3C | 109.5 | C15—C14—N2 | 121.13 (14) |
H3A—C3—H3C | 109.5 | C19—C14—N2 | 119.60 (13) |
H3B—C3—H3C | 109.5 | C14—C15—C16 | 120.56 (15) |
O1—C4—C3 | 109.5 (2) | C14—C15—H15 | 118.3 (12) |
O1—C4—C2 | 109.32 (18) | C16—C15—H15 | 121.2 (12) |
C3—C4—C2 | 113.6 (3) | C15—C16—C17 | 120.27 (16) |
O1—C4—C1 | 102.04 (18) | C15—C16—H16 | 120.4 (14) |
C3—C4—C1 | 111.0 (3) | C17—C16—H16 | 119.3 (14) |
C2—C4—C1 | 110.7 (3) | O4—C17—C18 | 122.96 (14) |
O2—C5—O1 | 125.72 (15) | O4—C17—C16 | 117.42 (14) |
O2—C5—N1 | 123.93 (15) | C18—C17—C16 | 119.62 (14) |
O1—C5—N1 | 110.35 (13) | C17—C18—C19 | 119.76 (14) |
N1—C6—C7 | 114.75 (13) | C17—C18—H18 | 120.0 (11) |
N1—C6—H6A | 106.6 (14) | C19—C18—H18 | 120.3 (11) |
C7—C6—H6A | 108.5 (14) | C14—C19—C18 | 120.52 (14) |
N1—C6—H6B | 108.5 (12) | C14—C19—H19 | 117.1 (11) |
C7—C6—H6B | 109.2 (12) | C18—C19—H19 | 122.3 (11) |
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+1/2, z+1/2; (iii) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H22N2O4 |
Mr | 342.39 |
Crystal system, space group | Monoclinic, 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) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.66 × 0.66 × 0.47 |
Data collection | |
Diffractometer | Rigaku Saturn724 CCD |
Absorption correction | Numerical (NUMABS; Higashi, 2000) |
Tmin, Tmax | 0.975, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15051, 4230, 3921 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.166, 1.13 |
No. of reflections | 4230 |
No. of parameters | 278 |
H-atom treatment | H 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).
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+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
Higashi, T. (2000). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Jiang, L. G. (2009). Chin. J. Struct. Chem. pp. 253–259. Google Scholar
McArdle, P. (1995). J. Appl. Cryst. 28, 65. CrossRef IUCr Journals Google Scholar
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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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.