Hydrogen bonds of four types (N-H
O=C, N-H
OH, O-H
O=C and O-H
OH) connect molecules of the title compound, C
14H
20N
2O
4, in the crystal into sheets folded into a zigzag pattern. The intermolecular interactions are discussed in terms of the first- through fourth-level graph sets, and a constructor graph helps visualize the supramolecular assembly.
Supporting information
CCDC reference: 645586
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N,
N'-bis(2-hydroxy-1-methylethyl)phthalamide
top
Crystal data top
C14H20N2O4 | F(000) = 600 |
Mr = 280.32 | Dx = 1.294 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 307 reflections |
a = 9.1548 (5) Å | θ = 2.4–28.3° |
b = 9.3937 (5) Å | µ = 0.10 mm−1 |
c = 16.7305 (10) Å | T = 100 K |
V = 1438.78 (14) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.20 × 0.20 mm |
Data collection top
Bruker SMART CCD 1000 area-detector diffractometer | 2063 independent reflections |
Radiation source: fine-focus sealed tube | 1817 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
0.30° ω and φ scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −12→12 |
Tmin = 0.954, Tmax = 0.981 | k = −12→12 |
23813 measured reflections | l = −21→22 |
Refinement top
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0415P)2 + 0.2593P] where P = (Fo2 + 2Fc2)/3 |
2063 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.49258 (14) | 1.00349 (13) | −0.14016 (7) | 0.0216 (3) | |
H1 | 0.5503 | 1.0444 | −0.1086 | 0.032* | |
O2 | 0.34758 (13) | 0.83846 (14) | 0.01344 (7) | 0.0237 (3) | |
O3 | 0.46207 (13) | 0.48608 (13) | 0.06256 (8) | 0.0246 (3) | |
O4 | 0.69968 (15) | 0.13805 (15) | −0.05119 (9) | 0.0310 (3) | |
H4 | 0.7807 | 0.0961 | −0.0523 | 0.047* | |
N1 | 0.56032 (15) | 0.75367 (15) | −0.03792 (8) | 0.0178 (3) | |
H1A | 0.6518 | 0.7326 | −0.0270 | 0.021* | |
N2 | 0.69365 (16) | 0.42920 (15) | 0.09785 (9) | 0.0198 (3) | |
H2 | 0.7759 | 0.4608 | 0.1185 | 0.024* | |
C1 | 0.5573 (2) | 0.87528 (18) | −0.16833 (10) | 0.0208 (4) | |
H1B | 0.6649 | 0.8847 | −0.1657 | 0.025* | |
H1C | 0.5301 | 0.8614 | −0.2251 | 0.025* | |
C2 | 0.51147 (18) | 0.74457 (18) | −0.12099 (9) | 0.0183 (3) | |
H2A | 0.4025 | 0.7378 | −0.1217 | 0.022* | |
C3 | 0.5746 (2) | 0.61087 (19) | −0.15947 (11) | 0.0247 (4) | |
H3A | 0.6816 | 0.6150 | −0.1577 | 0.037* | |
H3B | 0.5423 | 0.6050 | −0.2152 | 0.037* | |
H3C | 0.5407 | 0.5267 | −0.1302 | 0.037* | |
C4 | 0.47288 (18) | 0.79237 (17) | 0.02198 (10) | 0.0175 (3) | |
C5 | 0.53950 (18) | 0.78344 (18) | 0.10460 (10) | 0.0177 (3) | |
C6 | 0.5425 (2) | 0.9075 (2) | 0.14997 (11) | 0.0229 (4) | |
H6 | 0.5005 | 0.9924 | 0.1293 | 0.027* | |
C7 | 0.6066 (2) | 0.9080 (2) | 0.22533 (11) | 0.0259 (4) | |
H7 | 0.6084 | 0.9932 | 0.2559 | 0.031* | |
C8 | 0.6677 (2) | 0.7848 (2) | 0.25593 (10) | 0.0249 (4) | |
H8 | 0.7127 | 0.7857 | 0.3071 | 0.030* | |
C9 | 0.66311 (18) | 0.6598 (2) | 0.21169 (10) | 0.0215 (3) | |
H9 | 0.7041 | 0.5750 | 0.2330 | 0.026* | |
C10 | 0.59847 (18) | 0.65806 (18) | 0.13588 (9) | 0.0170 (3) | |
C11 | 0.58002 (18) | 0.51709 (18) | 0.09402 (9) | 0.0174 (3) | |
C12 | 0.68780 (19) | 0.28252 (17) | 0.06926 (10) | 0.0195 (3) | |
H12 | 0.5871 | 0.2447 | 0.0786 | 0.023* | |
C13 | 0.7952 (2) | 0.1921 (2) | 0.11607 (12) | 0.0301 (4) | |
H13A | 0.8941 | 0.2299 | 0.1090 | 0.045* | |
H13B | 0.7915 | 0.0938 | 0.0966 | 0.045* | |
H13C | 0.7694 | 0.1942 | 0.1729 | 0.045* | |
C14 | 0.7188 (2) | 0.27850 (19) | −0.02015 (11) | 0.0246 (4) | |
H14A | 0.6520 | 0.3448 | −0.0481 | 0.030* | |
H14B | 0.8203 | 0.3104 | −0.0301 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0230 (6) | 0.0190 (6) | 0.0229 (6) | 0.0034 (5) | −0.0002 (5) | −0.0018 (5) |
O2 | 0.0162 (6) | 0.0286 (6) | 0.0263 (6) | 0.0015 (5) | 0.0009 (5) | 0.0025 (6) |
O3 | 0.0216 (6) | 0.0250 (6) | 0.0271 (6) | −0.0040 (5) | −0.0054 (5) | 0.0002 (5) |
O4 | 0.0269 (7) | 0.0292 (7) | 0.0369 (8) | 0.0089 (6) | −0.0080 (6) | −0.0136 (6) |
N1 | 0.0152 (6) | 0.0223 (7) | 0.0159 (6) | 0.0006 (6) | −0.0021 (5) | 0.0011 (5) |
N2 | 0.0197 (7) | 0.0191 (7) | 0.0207 (7) | −0.0035 (6) | −0.0026 (6) | −0.0010 (6) |
C1 | 0.0236 (8) | 0.0210 (8) | 0.0178 (8) | 0.0036 (7) | 0.0036 (7) | 0.0005 (7) |
C2 | 0.0189 (7) | 0.0201 (7) | 0.0160 (7) | 0.0008 (7) | −0.0024 (6) | 0.0001 (6) |
C3 | 0.0335 (10) | 0.0188 (8) | 0.0218 (8) | 0.0022 (7) | −0.0066 (8) | −0.0028 (7) |
C4 | 0.0170 (7) | 0.0158 (7) | 0.0196 (8) | −0.0025 (6) | −0.0002 (6) | 0.0018 (6) |
C5 | 0.0136 (7) | 0.0226 (8) | 0.0171 (7) | −0.0020 (6) | 0.0037 (6) | 0.0000 (6) |
C6 | 0.0216 (8) | 0.0228 (8) | 0.0243 (9) | 0.0023 (7) | 0.0044 (7) | −0.0022 (7) |
C7 | 0.0267 (9) | 0.0279 (9) | 0.0232 (9) | −0.0018 (8) | 0.0037 (7) | −0.0100 (7) |
C8 | 0.0253 (9) | 0.0352 (10) | 0.0143 (8) | −0.0027 (8) | 0.0012 (7) | −0.0037 (7) |
C9 | 0.0205 (8) | 0.0256 (8) | 0.0183 (8) | −0.0011 (7) | 0.0009 (7) | 0.0020 (7) |
C10 | 0.0152 (7) | 0.0208 (8) | 0.0150 (7) | −0.0028 (7) | 0.0030 (6) | −0.0009 (6) |
C11 | 0.0202 (8) | 0.0193 (8) | 0.0129 (7) | −0.0034 (6) | 0.0013 (6) | 0.0026 (6) |
C12 | 0.0197 (8) | 0.0160 (7) | 0.0226 (8) | −0.0023 (7) | −0.0010 (7) | 0.0011 (6) |
C13 | 0.0356 (11) | 0.0206 (8) | 0.0341 (10) | −0.0014 (8) | −0.0105 (9) | 0.0045 (8) |
C14 | 0.0277 (9) | 0.0234 (9) | 0.0227 (9) | 0.0049 (8) | −0.0011 (7) | −0.0015 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.423 (2) | C4—C5 | 1.513 (2) |
O1—H1 | 0.8400 | C5—C6 | 1.391 (2) |
O2—C4 | 1.234 (2) | C5—C10 | 1.397 (2) |
O3—C11 | 1.236 (2) | C6—C7 | 1.391 (3) |
O4—C14 | 1.429 (2) | C6—H6 | 0.9500 |
O4—H4 | 0.8400 | C7—C8 | 1.384 (3) |
N1—C4 | 1.333 (2) | C7—H7 | 0.9500 |
N1—C2 | 1.462 (2) | C8—C9 | 1.389 (2) |
N1—H1A | 0.8800 | C8—H8 | 0.9500 |
N2—C11 | 1.330 (2) | C9—C10 | 1.400 (2) |
N2—C12 | 1.460 (2) | C9—H9 | 0.9500 |
N2—H2 | 0.8800 | C10—C11 | 1.507 (2) |
C1—C2 | 1.520 (2) | C12—C13 | 1.517 (3) |
C1—H1B | 0.9900 | C12—C14 | 1.523 (2) |
C1—H1C | 0.9900 | C12—H12 | 1.0000 |
C2—C3 | 1.525 (2) | C13—H13A | 0.9800 |
C2—H2A | 1.0000 | C13—H13B | 0.9800 |
C3—H3A | 0.9800 | C13—H13C | 0.9800 |
C3—H3B | 0.9800 | C14—H14A | 0.9900 |
C3—H3C | 0.9800 | C14—H14B | 0.9900 |
| | | |
C1—O1—H1 | 109.5 | C5—C6—H6 | 119.8 |
C14—O4—H4 | 109.5 | C8—C7—C6 | 120.19 (16) |
C4—N1—C2 | 123.14 (14) | C8—C7—H7 | 119.9 |
C4—N1—H1A | 118.4 | C6—C7—H7 | 119.9 |
C2—N1—H1A | 118.4 | C7—C8—C9 | 119.86 (16) |
C11—N2—C12 | 122.79 (15) | C7—C8—H8 | 120.1 |
C11—N2—H2 | 118.6 | C9—C8—H8 | 120.1 |
C12—N2—H2 | 118.6 | C8—C9—C10 | 120.38 (16) |
O1—C1—C2 | 113.34 (13) | C8—C9—H9 | 119.8 |
O1—C1—H1B | 108.9 | C10—C9—H9 | 119.8 |
C2—C1—H1B | 108.9 | C5—C10—C9 | 119.53 (15) |
O1—C1—H1C | 108.9 | C5—C10—C11 | 121.54 (14) |
C2—C1—H1C | 108.9 | C9—C10—C11 | 118.60 (15) |
H1B—C1—H1C | 107.7 | O3—C11—N2 | 123.89 (16) |
N1—C2—C1 | 111.31 (14) | O3—C11—C10 | 120.18 (15) |
N1—C2—C3 | 109.47 (14) | N2—C11—C10 | 115.81 (14) |
C1—C2—C3 | 109.91 (14) | N2—C12—C13 | 109.60 (14) |
N1—C2—H2A | 108.7 | N2—C12—C14 | 109.79 (14) |
C1—C2—H2A | 108.7 | C13—C12—C14 | 111.86 (15) |
C3—C2—H2A | 108.7 | N2—C12—H12 | 108.5 |
C2—C3—H3A | 109.5 | C13—C12—H12 | 108.5 |
C2—C3—H3B | 109.5 | C14—C12—H12 | 108.5 |
H3A—C3—H3B | 109.5 | C12—C13—H13A | 109.5 |
C2—C3—H3C | 109.5 | C12—C13—H13B | 109.5 |
H3A—C3—H3C | 109.5 | H13A—C13—H13B | 109.5 |
H3B—C3—H3C | 109.5 | C12—C13—H13C | 109.5 |
O2—C4—N1 | 124.51 (16) | H13A—C13—H13C | 109.5 |
O2—C4—C5 | 119.99 (15) | H13B—C13—H13C | 109.5 |
N1—C4—C5 | 115.44 (14) | O4—C14—C12 | 110.92 (15) |
C6—C5—C10 | 119.61 (15) | O4—C14—H14A | 109.5 |
C6—C5—C4 | 117.39 (15) | C12—C14—H14A | 109.5 |
C10—C5—C4 | 122.99 (15) | O4—C14—H14B | 109.5 |
C7—C6—C5 | 120.41 (17) | C12—C14—H14B | 109.5 |
C7—C6—H6 | 119.8 | H14A—C14—H14B | 108.0 |
| | | |
C4—N1—C2—C1 | 100.23 (18) | C4—C5—C10—C9 | 177.60 (15) |
C4—N1—C2—C3 | −138.06 (16) | C6—C5—C10—C11 | 171.67 (15) |
O1—C1—C2—N1 | −63.55 (18) | C4—C5—C10—C11 | −9.1 (2) |
O1—C1—C2—C3 | 175.00 (15) | C8—C9—C10—C5 | 0.5 (2) |
C2—N1—C4—O2 | −7.9 (3) | C8—C9—C10—C11 | −172.95 (15) |
C2—N1—C4—C5 | 175.00 (15) | C12—N2—C11—O3 | −3.8 (3) |
O2—C4—C5—C6 | −54.9 (2) | C12—N2—C11—C10 | 172.25 (14) |
N1—C4—C5—C6 | 122.36 (17) | C5—C10—C11—O3 | −40.4 (2) |
O2—C4—C5—C10 | 125.89 (18) | C9—C10—C11—O3 | 132.97 (17) |
N1—C4—C5—C10 | −56.8 (2) | C5—C10—C11—N2 | 143.40 (16) |
C10—C5—C6—C7 | 1.4 (3) | C9—C10—C11—N2 | −43.3 (2) |
C4—C5—C6—C7 | −177.82 (15) | C11—N2—C12—C13 | −151.80 (16) |
C5—C6—C7—C8 | −0.1 (3) | C11—N2—C12—C14 | 85.0 (2) |
C6—C7—C8—C9 | −0.9 (3) | N2—C12—C14—O4 | −174.30 (14) |
C7—C8—C9—C10 | 0.8 (3) | C13—C12—C14—O4 | 63.8 (2) |
C6—C5—C10—C9 | −1.6 (2) | | |
Hydrogen-bond geometry (Å, °) top | D—H···A | D—H | H···A | D···A | D—H···A |
a | N1—H1A···O2i | 0.88 | 1.93 | 2.7990 (14) | 171 |
b | N2—H2···O1i | 0.88 | 2.04 | 2.8961 (15) | 163 |
c | O1—H1···O4ii | 0.84 | 1.89 | 2.7227 (14) | 170 |
d | O4—H4···O3iii | 0.84 | 1.84 | 2.6773 (14) | 174 |
| C2—H2A···Cgiv | 1.00 | 2.921 | 3.880 (2) | 161 |
| C8—H8···O4vii | 0.95 | 2.60 | 3.5235 (18) | 163 |
| C3—H3B···Oviii | 0.98 | 2.62 | 3.5542 (17) | 159 |
Symmetry codes: (i) x + 1/2, -y + 3/2, -z; (ii) x, y + 1, z;
(iii) x + 1/2, -y + 1/2, -z; (iv) x - 1/2, -y + 3/2, -z;
(vii) -x + 3/2,
-y + 1, z + 1/2; (viii) -x + 1, y - 1/2, -z - 1/2. |