Constructor graph description of hydrogen bonding in a supra­molecular assembly of N,N'-bis­(2-hydr­oxy-1-methyl­ethyl)phthalamide

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, C₁₄H₂₀N₂O₄, 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.

Computing details

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

Crystal data

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) Å^3	Block, colourless
Z = 4	0.50 × 0.20 × 0.20 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.2593P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)