N,N'-Bis(2-carboxy­ethyl)-1,4,5,8-naphthalene­tetra­carboxyl­ic di­imine di­methyl­form­amide disolvate

In the title compound, C₂₀H₁₄N₂O₈·2C₃H₇NO, the essentially planar C₂₀H₁₄N₂O₈ mol­ecule is centrosymmetric and is hydrogen bonded via the carboxyl­ic acid H atoms to the aldehyde O atom of the di­methyl­form­amide mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.108
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O15    ..  C20     ..       3.01 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: Collect (Nonius, 1997–2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N,N'-Bis(2-carboxyethyl)-1,4,5,8-naphthalenetetracarboxylic diimine dimethylformamide disolvate

Crystal data

C20H14N2O8·2C3H7NO	Z = 1
Mr = 556.52	F(000) = 292
Triclinic, P1	Dx = 1.450 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9519 (1) Å	Cell parameters from 11976 reflections
b = 10.8758 (2) Å	θ = 3.1–28.3°
c = 12.9078 (3) Å	µ = 0.11 mm^−1
α = 111.985 (1)°	T = 123 K
β = 95.578 (1)°	Plate, red
γ = 94.095 (1)°	0.26 × 0.12 × 0.05 mm
V = 637.17 (2) Å^3

Data collection

Nonius KappaCCD diffractometer	2266 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Horizonally mounted graphite crystal monochromator	θmax = 28.3°, θmin = 3.1°
Detector resolution: 9 pixels mm^-1	h = −6→6
CCD scans	k = −14→14
11976 measured reflections	l = −17→17
3132 independent reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.1167P] where P = (Fo^2 + 2Fc^2)/3
3132 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.26 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
C1	0.4386 (3)	0.49628 (13)	0.23584 (12)	0.0214 (3)
C2	0.4498 (3)	0.57134 (13)	0.15918 (11)	0.0202 (3)
H2A	0.3526	0.5146	0.0836	0.024*
H2B	0.6426	0.5923	0.1511	0.024*
C3	0.3198 (3)	0.70013 (13)	0.20541 (12)	0.0206 (3)
H3A	0.1200	0.6786	0.1999	0.025*
H3B	0.3925	0.7486	0.2860	0.025*
N4	0.3746 (2)	0.78706 (11)	0.14326 (9)	0.0187 (3)
C5	0.6107 (3)	0.87750 (13)	0.18261 (11)	0.0180 (3)
C6	0.6592 (2)	0.96879 (13)	0.12316 (11)	0.0169 (3)
C7	0.4761 (2)	0.95622 (12)	0.02825 (11)	0.0150 (3)
C8	0.2454 (2)	0.85935 (12)	−0.01183 (11)	0.0163 (3)
C9	0.1893 (3)	0.76971 (13)	0.04845 (11)	0.0190 (3)
O10	−0.0095 (2)	0.68612 (10)	0.01956 (9)	0.0281 (3)
C11	0.0698 (3)	0.84859 (13)	−0.10511 (11)	0.0191 (3)
H11	−0.0844	0.7826	−0.1317	0.023*
C12	0.8817 (3)	1.06495 (13)	0.16099 (11)	0.0192 (3)
H12	1.0033	1.0729	0.2254	0.023*
O13	0.7657 (2)	0.88150 (10)	0.26362 (8)	0.0258 (2)
O14	0.5612 (2)	0.38693 (10)	0.20171 (9)	0.0295 (3)
H14	0.5486	0.3485	0.2469	0.035*
O15	0.3318 (3)	0.53306 (12)	0.32075 (10)	0.0419 (3)
O16	0.4929 (2)	0.25131 (10)	0.33046 (9)	0.0319 (3)
C17	0.3413 (3)	0.29651 (14)	0.40350 (12)	0.0254 (3)
H17	0.2954	0.3843	0.4187	0.030*
N18	0.2389 (2)	0.23137 (12)	0.46183 (10)	0.0243 (3)
C19	0.3013 (3)	0.09786 (15)	0.44595 (13)	0.0314 (4)
H19A	0.1389	0.0338	0.4078	0.047*
H19B	0.3569	0.0938	0.5195	0.047*
H19C	0.4503	0.0756	0.3998	0.047*
C20	0.0541 (3)	0.29017 (18)	0.54327 (14)	0.0368 (4)
H20A	0.0421	0.3829	0.5517	0.055*
H20B	0.1234	0.2879	0.6162	0.055*
H20C	−0.1276	0.2393	0.5167	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0247 (7)	0.0179 (7)	0.0227 (8)	0.0014 (6)	0.0037 (6)	0.0093 (6)
C2	0.0243 (7)	0.0185 (7)	0.0189 (7)	0.0004 (6)	0.0036 (5)	0.0086 (6)
C3	0.0226 (7)	0.0222 (7)	0.0239 (7)	0.0013 (6)	0.0059 (5)	0.0164 (6)
N4	0.0205 (5)	0.0191 (6)	0.0216 (6)	0.0019 (5)	0.0054 (5)	0.0129 (5)
C5	0.0198 (6)	0.0163 (6)	0.0197 (7)	0.0037 (5)	0.0054 (5)	0.0080 (5)
C6	0.0187 (6)	0.0158 (6)	0.0179 (7)	0.0043 (5)	0.0058 (5)	0.0073 (5)
C7	0.0155 (6)	0.0131 (6)	0.0174 (7)	0.0042 (5)	0.0058 (5)	0.0056 (5)
C8	0.0172 (6)	0.0140 (6)	0.0193 (7)	0.0029 (5)	0.0050 (5)	0.0073 (5)
C9	0.0194 (6)	0.0172 (6)	0.0221 (7)	0.0023 (5)	0.0044 (5)	0.0092 (6)
O10	0.0269 (5)	0.0258 (5)	0.0348 (6)	−0.0074 (4)	−0.0008 (4)	0.0183 (5)
C11	0.0179 (6)	0.0160 (6)	0.0229 (7)	−0.0010 (5)	0.0025 (5)	0.0073 (5)
C12	0.0203 (6)	0.0190 (7)	0.0179 (7)	0.0018 (5)	0.0005 (5)	0.0071 (5)
O13	0.0286 (5)	0.0279 (5)	0.0242 (6)	−0.0002 (4)	−0.0022 (4)	0.0158 (4)
O14	0.0439 (6)	0.0240 (5)	0.0304 (6)	0.0139 (5)	0.0149 (5)	0.0171 (5)
O15	0.0669 (8)	0.0372 (7)	0.0420 (7)	0.0263 (6)	0.0335 (6)	0.0286 (6)
O16	0.0443 (6)	0.0316 (6)	0.0304 (6)	0.0144 (5)	0.0154 (5)	0.0195 (5)
C17	0.0321 (8)	0.0229 (7)	0.0248 (8)	0.0069 (6)	0.0040 (6)	0.0126 (6)
N18	0.0259 (6)	0.0265 (6)	0.0241 (7)	0.0037 (5)	0.0035 (5)	0.0138 (5)
C19	0.0442 (9)	0.0249 (8)	0.0286 (9)	0.0010 (7)	0.0000 (7)	0.0158 (7)
C20	0.0311 (8)	0.0518 (11)	0.0362 (10)	0.0120 (8)	0.0124 (7)	0.0236 (8)

Geometric parameters (Å, º)

C1—O15	1.2065 (17)	C8—C9	1.4847 (18)
C1—O14	1.3189 (16)	C9—O10	1.2175 (16)
C1—C2	1.5025 (18)	C11—C12^i	1.4041 (18)
C2—C3	1.5198 (18)	C11—H11	0.9500
C2—H2A	0.9900	C12—C11^i	1.4041 (18)
C2—H2B	0.9900	C12—H12	0.9500
C3—N4	1.4779 (16)	O14—H14	0.8400
C3—H3A	0.9900	O16—C17	1.2400 (17)
C3—H3B	0.9900	C17—N18	1.3221 (18)
N4—C5	1.3924 (17)	C17—H17	0.9500
N4—C9	1.3997 (17)	N18—C19	1.4490 (18)
C5—O13	1.2205 (16)	N18—C20	1.4556 (19)
C5—C6	1.4847 (18)	C19—H19A	0.9800
C6—C12	1.3764 (18)	C19—H19B	0.9800
C6—C7	1.4079 (18)	C19—H19C	0.9800
C7—C8	1.4098 (17)	C20—H20A	0.9800
C7—C7^i	1.420 (2)	C20—H20B	0.9800
C8—C11	1.3769 (18)	C20—H20C	0.9800
O15—C1—O14	123.37 (13)	C7—C8—C9	119.53 (11)
O15—C1—C2	123.53 (12)	O10—C9—N4	120.51 (12)
O14—C1—C2	113.09 (11)	O10—C9—C8	122.69 (12)
C1—C2—C3	111.07 (11)	N4—C9—C8	116.78 (11)
C1—C2—H2A	109.4	C8—C11—C12^i	120.09 (12)
C3—C2—H2A	109.4	C8—C11—H11	120.0
C1—C2—H2B	109.4	C12^i—C11—H11	120.0
C3—C2—H2B	109.4	C6—C12—C11^i	120.48 (12)
H2A—C2—H2B	108.0	C6—C12—H12	119.8
N4—C3—C2	111.71 (11)	C11^i—C12—H12	119.8
N4—C3—H3A	109.3	C1—O14—H14	109.5
C2—C3—H3A	109.3	O16—C17—N18	124.78 (13)
N4—C3—H3B	109.3	O16—C17—H17	117.6
C2—C3—H3B	109.3	N18—C17—H17	117.6
H3A—C3—H3B	107.9	C17—N18—C19	121.57 (12)
C5—N4—C9	125.39 (11)	C17—N18—C20	121.19 (12)
C5—N4—C3	117.02 (11)	C19—N18—C20	117.23 (12)
C9—N4—C3	117.57 (11)	N18—C19—H19A	109.5
O13—C5—N4	120.55 (12)	N18—C19—H19B	109.5
O13—C5—C6	122.49 (12)	H19A—C19—H19B	109.5
N4—C5—C6	116.94 (11)	N18—C19—H19C	109.5
C12—C6—C7	120.47 (11)	H19A—C19—H19C	109.5
C12—C6—C5	119.99 (12)	H19B—C19—H19C	109.5
C7—C6—C5	119.54 (11)	N18—C20—H20A	109.5
C6—C7—C8	121.69 (11)	N18—C20—H20B	109.5
C6—C7—C7^i	119.23 (14)	H20A—C20—H20B	109.5
C8—C7—C7^i	119.08 (15)	N18—C20—H20C	109.5
C11—C8—C7	120.66 (11)	H20A—C20—H20C	109.5
C11—C8—C9	119.80 (11)	H20B—C20—H20C	109.5

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O16	0.84	1.80	2.6315 (14)	173