N,N,N′,N′-Tetra­kis(carboxy­meth­yl)-2,2′-(ethyl­ene­dioxy)­dianilinium dichloride dihydrate

Raynor, J.W.; Chruszcz, M.; Minor, W.

doi:10.1107/S1600536807001559

N,N,N',N'-Tetrakis(carboxymethyl)-2,2'-(ethylenedioxy)dianilinium dichloride dihydrate

In the title compound, C₂₂H₂₆N₂O₁₀²⁺·2Cl^-·2H₂O, the asymmetric unit contains one-half cation, one chloride ion and one water molecule. The cation is located on a center of inversion. The system containing both benzene rings and the linker between them is almost planar, while the acid side-chains are oriented nearly perpendicular to that plane. The crystal structure is stabilized by several hydrogen bonds and also by ionic interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001559/gk2053sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001559/gk2053Isup2.hkl Contains datablock I

CCDC reference: 636645

checkCIF report

Key indicators

Single-crystal X-ray study
T = 119 K
Mean (C-C) = 0.002 Å
R factor = 0.034
wR factor = 0.097
Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        100 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.59 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: HKL-2000 (Otwinowski & Minor, 1997); cell refinement: HKL-2000; data reduction: HKL-2000; program(s) used to solve structure: HKL-3000SM (Minor et al., 2006) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: HKL-3000SM and SHELXL97 (Sheldrick, 1997); molecular graphics: HKL-3000SM, ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: HKL-3000SM.

N,N,N',N'-Tetrakis(carboxymethyl)-2,2'-(ethylenedioxy)dianilinium dichloride dihydrate top

Crystal data top

C₂₂H₂₆N₂O₁₀²⁺·2Cl⁻·2H₂O	F(000) = 612.0
M_r = 585.38	D_x = 1.466 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71074 Å
Hall symbol: -P 2yc	Cell parameters from 104679 reflections
a = 10.358 (1) Å	θ = 2.7–29.6°
b = 6.183 (1) Å	µ = 0.31 mm⁻¹
c = 20.726 (1) Å	T = 119 K
β = 92.48 (1)°	Needle, colorless
V = 1326.1 (3) Å³	0.48 × 0.06 × 0.05 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	3680 independent reflections
Radiation source: fine-focus sealed tube	3028 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 10 pixels mm^-1	θ_max = 29.6°, θ_min = 2.7°
ω scan with χ offset	h = −14→14
Absorption correction: multi-scan (Otwinowski et al., 2003)	k = −8→8
T_min = 0.98, T_max = 0.99	l = −28→28
104679 measured reflections

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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F²) = 0.098	All H-atom parameters refined
S = 1.07	w = 1/[σ²(F_o²) + (0.055P)² + 0.2141P] where P = (F_o² + 2F_c²)/3
3680 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.20 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	U_iso*/U_eq
N1	0.75181 (9)	0.14452 (17)	0.35268 (4)	0.0194 (2)
O1	0.88330 (9)	0.32828 (16)	0.46000 (4)	0.0299 (2)
O3	1.06751 (8)	−0.07096 (17)	0.31663 (4)	0.0268 (2)
O2	0.88432 (9)	−0.23822 (15)	0.34198 (5)	0.0293 (2)
O4	0.49036 (9)	0.16655 (17)	0.33024 (5)	0.0354 (2)
C7	0.73920 (11)	0.0609 (2)	0.41918 (5)	0.0215 (2)
O6	0.34531 (11)	0.8858 (2)	0.24346 (5)	0.0353 (2)
C9	0.94381 (11)	−0.0772 (2)	0.33042 (5)	0.0221 (2)
C8	0.88761 (11)	0.1488 (2)	0.32911 (6)	0.0214 (2)
C2	0.80646 (12)	0.1551 (2)	0.47186 (6)	0.0260 (3)
C11	0.54362 (12)	0.3354 (2)	0.34237 (6)	0.0234 (2)
O5	0.48471 (10)	0.51776 (16)	0.35471 (6)	0.0384 (3)
C10	0.68913 (11)	0.3614 (2)	0.34388 (6)	0.0235 (2)
C6	0.65707 (13)	−0.1124 (2)	0.42769 (6)	0.0275 (3)
C1	0.96152 (14)	0.4091 (3)	0.51394 (6)	0.0316 (3)
C4	0.70976 (16)	−0.1080 (3)	0.54112 (7)	0.0395 (3)
C3	0.79060 (15)	0.0669 (3)	0.53296 (7)	0.0359 (3)
C5	0.64209 (15)	−0.1977 (3)	0.48879 (7)	0.0365 (3)
Cl1	0.79733 (3)	0.50040 (5)	0.181411 (14)	0.02543 (10)
H1A	0.9037 (16)	0.465 (3)	0.5480 (8)	0.031 (4)*
H6	0.6100 (16)	−0.171 (3)	0.3898 (8)	0.030 (4)*
H10A	0.7138 (14)	0.419 (3)	0.3030 (7)	0.023 (4)*
H10B	0.7233 (16)	0.454 (3)	0.3783 (8)	0.031 (4)*
H8A	0.8822 (14)	0.195 (3)	0.2857 (7)	0.024 (4)*
H1B	1.0247 (17)	0.296 (3)	0.5308 (8)	0.034 (4)*
H8B	0.9387 (14)	0.246 (2)	0.3533 (7)	0.022 (3)*
HO3	1.100 (2)	−0.208 (4)	0.3175 (10)	0.058 (6)*
H3	0.832 (2)	0.129 (3)	0.5670 (10)	0.050 (5)*
HN1	0.7128 (16)	0.048 (3)	0.3266 (8)	0.030 (4)*
H5	0.5827 (19)	−0.320 (3)	0.4957 (9)	0.047 (5)*
HO6A	0.301 (2)	0.799 (4)	0.2623 (10)	0.049 (6)*
HO6B	0.395 (3)	0.946 (4)	0.2673 (12)	0.071 (7)*
HO5	0.391 (3)	0.511 (4)	0.3460 (12)	0.079 (8)*
H4	0.6990 (17)	−0.172 (3)	0.5850 (9)	0.046 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0182 (4)	0.0219 (5)	0.0179 (4)	−0.0008 (4)	−0.0008 (3)	−0.0010 (4)
O1	0.0318 (5)	0.0362 (5)	0.0212 (4)	−0.0121 (4)	−0.0040 (3)	−0.0030 (4)
O3	0.0207 (4)	0.0305 (5)	0.0294 (4)	0.0041 (4)	0.0019 (3)	0.0024 (4)
O2	0.0264 (4)	0.0258 (5)	0.0358 (5)	0.0008 (4)	0.0027 (4)	0.0006 (4)
O4	0.0227 (4)	0.0303 (5)	0.0530 (6)	−0.0018 (4)	−0.0015 (4)	−0.0133 (4)
C7	0.0210 (5)	0.0237 (6)	0.0198 (5)	0.0013 (4)	0.0014 (4)	0.0007 (4)
O6	0.0296 (5)	0.0411 (6)	0.0344 (5)	−0.0102 (5)	−0.0087 (4)	0.0153 (5)
C9	0.0207 (5)	0.0289 (6)	0.0167 (5)	0.0021 (5)	−0.0012 (4)	−0.0001 (4)
C8	0.0191 (5)	0.0244 (6)	0.0208 (5)	−0.0003 (5)	0.0017 (4)	0.0004 (4)
C2	0.0247 (6)	0.0314 (7)	0.0218 (5)	−0.0026 (5)	−0.0003 (4)	−0.0010 (5)
C11	0.0216 (5)	0.0259 (6)	0.0225 (5)	0.0014 (5)	−0.0012 (4)	−0.0001 (4)
O5	0.0219 (5)	0.0253 (5)	0.0674 (7)	0.0039 (4)	−0.0054 (5)	−0.0047 (5)
C10	0.0202 (5)	0.0221 (6)	0.0282 (6)	0.0011 (4)	−0.0010 (4)	0.0024 (5)
C6	0.0281 (6)	0.0251 (7)	0.0297 (6)	−0.0014 (5)	0.0035 (5)	−0.0001 (5)
C1	0.0314 (7)	0.0402 (8)	0.0226 (6)	−0.0075 (6)	−0.0055 (5)	−0.0047 (5)
C4	0.0462 (8)	0.0453 (9)	0.0274 (6)	−0.0016 (7)	0.0072 (6)	0.0102 (6)
C3	0.0393 (7)	0.0474 (8)	0.0208 (6)	−0.0041 (7)	−0.0013 (5)	0.0010 (6)
C5	0.0406 (8)	0.0325 (8)	0.0370 (7)	−0.0056 (6)	0.0103 (6)	0.0061 (6)
Cl1	0.02147 (15)	0.02640 (17)	0.02836 (15)	−0.00265 (11)	0.00037 (10)	−0.00190 (11)

Geometric parameters (Å, º) top

N1—C7	1.4831 (14)	C2—C3	1.3949 (18)
N1—C10	1.4975 (16)	C11—O5	1.3124 (16)
N1—C8	1.5091 (15)	C11—C10	1.5147 (17)
N1—HN1	0.890 (18)	O5—HO5	0.98 (3)
O1—C2	1.3630 (16)	C10—H10A	0.965 (15)
O1—C1	1.4414 (15)	C10—H10B	0.969 (17)
O3—C9	1.3252 (15)	C6—C5	1.3865 (19)
O3—HO3	0.91 (2)	C6—H6	0.977 (16)
O2—C9	1.2006 (16)	C1—C1ⁱ	1.508 (3)
O4—C11	1.2024 (16)	C1—H1A	1.007 (17)
C7—C6	1.3840 (18)	C1—H1B	1.010 (18)
C7—C2	1.3967 (16)	C4—C3	1.383 (2)
O6—HO6A	0.81 (2)	C4—C5	1.382 (2)
O6—HO6B	0.79 (3)	C4—H4	1.002 (19)
C9—C8	1.5133 (18)	C3—H3	0.90 (2)
C8—H8A	0.943 (15)	C5—H5	0.99 (2)
C8—H8B	0.932 (16)

C7—N1—C10	111.73 (9)	O5—C11—C10	112.05 (11)
C7—N1—C8	115.32 (9)	C11—O5—HO5	113.1 (14)
C10—N1—C8	110.50 (9)	N1—C10—C11	109.47 (10)
C7—N1—HN1	105.9 (11)	N1—C10—H10A	108.1 (10)
C10—N1—HN1	110.1 (11)	C11—C10—H10A	108.8 (9)
C8—N1—HN1	102.7 (10)	N1—C10—H10B	107.3 (10)
C2—O1—C1	116.46 (10)	C11—C10—H10B	114.1 (10)
C9—O3—HO3	109.1 (14)	H10A—C10—H10B	109.0 (14)
C6—C7—C2	120.76 (11)	C7—C6—C5	120.30 (13)
C6—C7—N1	117.88 (10)	C7—C6—H6	118.2 (9)
C2—C7—N1	121.34 (11)	C5—C6—H6	121.5 (10)
HO6A—O6—HO6B	112 (2)	O1—C1—C1ⁱ	104.47 (13)
O2—C9—O3	125.19 (12)	O1—C1—H1A	109.4 (10)
O2—C9—C8	124.67 (11)	C1ⁱ—C1—H1A	110.8 (10)
O3—C9—C8	110.13 (11)	O1—C1—H1B	111.3 (10)
N1—C8—C9	109.96 (10)	C1ⁱ—C1—H1B	107.7 (10)
N1—C8—H8A	107.2 (9)	H1A—C1—H1B	112.9 (13)
C9—C8—H8A	107.8 (9)	C3—C4—C5	120.47 (13)
N1—C8—H8B	110.7 (9)	C3—C4—H4	120.8 (11)
C9—C8—H8B	112.1 (9)	C5—C4—H4	118.8 (11)
H8A—C8—H8B	108.9 (13)	C4—C3—C2	120.82 (13)
O1—C2—C3	124.28 (12)	C4—C3—H3	120.7 (13)
O1—C2—C7	117.52 (10)	C2—C3—H3	118.5 (13)
C3—C2—C7	118.20 (12)	C4—C5—C6	119.42 (14)
O4—C11—O5	125.01 (12)	C4—C5—H5	119.4 (11)
O4—C11—C10	122.92 (11)	C6—C5—H5	121.1 (11)

C10—N1—C7—C6	109.19 (12)	N1—C7—C2—C3	−179.57 (12)
C8—N1—C7—C6	−123.55 (12)	C7—N1—C10—C11	−72.14 (12)
C10—N1—C7—C2	−69.97 (14)	C8—N1—C10—C11	158.04 (9)
C8—N1—C7—C2	57.29 (15)	O4—C11—C10—N1	−20.62 (17)
C7—N1—C8—C9	59.19 (13)	O5—C11—C10—N1	160.38 (11)
C10—N1—C8—C9	−172.92 (9)	C2—C7—C6—C5	−1.1 (2)
O2—C9—C8—N1	7.22 (16)	N1—C7—C6—C5	179.70 (12)
O3—C9—C8—N1	−173.13 (9)	C2—O1—C1—C1ⁱ	177.77 (14)
C1—O1—C2—C3	6.2 (2)	C5—C4—C3—C2	−0.6 (3)
C1—O1—C2—C7	−174.01 (12)	O1—C2—C3—C4	179.37 (14)
C6—C7—C2—O1	−178.51 (12)	C7—C2—C3—C4	−0.4 (2)
N1—C7—C2—O1	0.62 (18)	C3—C4—C5—C6	0.8 (3)
C6—C7—C2—C3	1.3 (2)	C7—C6—C5—C4	0.1 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···Cl1ⁱⁱ	0.91 (2)	2.09 (2)	2.9968 (11)	171 (2)
N1—HN1···O6ⁱⁱⁱ	0.89 (2)	1.84 (2)	2.7146 (14)	165 (2)
O6—HO6A···Cl1^iv	0.81 (2)	2.43 (2)	3.2378 (12)	170 (2)
O6—HO6B···O4^v	0.79 (3)	2.10 (3)	2.8761 (15)	166 (3)
O5—HO5···Cl1^iv	0.98 (3)	2.01 (3)	2.9862 (11)	174 (2)

Symmetry codes: (ii) −x+2, y−1, −z+1/2; (iii) −x+1, y−1, −z+1/2; (iv) −x+1, y, −z+1/2; (v) x, y+1, z.

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N,N,N',N'-Tetra­kis(carboxy­meth­yl)-2,2'-(ethyl­ene­dioxy)­dianilinium dichloride dihydrate

Supporting information

Key indicators

checkCIF/PLATON results

N,N,N',N'-Tetrakis(carboxymethyl)-2,2'-(ethylenedioxy)dianilinium dichloride dihydrate