Redetermination of 3,4-dimethoxy­phenyl­ethyl­ammonium chloride dihydrate

The structure of the title compound, C₁₀H₁₆NO₂⁺·Cl⁻·2H₂O, has been redetermined. It is stabilized by O—H...Cl, O—H...O, N—H...O and N—H...Cl hydrogen-bonding inter­actions, which build up an intricate three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.055
• wR factor = 0.161
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.04
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

3,4-Dimethoxyphenylethylammonium chloride dihydrate

Crystal data

C10H16NO2^+·Cl^−·2H2O	F(000) = 544
Mr = 253.72	Dx = 1.278 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2799 reflections
a = 11.565 (2) Å	θ = 4.6–51.3°
b = 13.760 (3) Å	µ = 0.29 mm^−1
c = 8.3165 (16) Å	T = 293 K
β = 94.955 (4)°	Plate, colourless
V = 1318.5 (4) Å^3	0.50 × 0.50 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2861 independent reflections
Radiation source: fine-focus sealed tube	2161 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.099
φ and ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −14→14
Tmin = 0.858, Tmax = 0.923	k = −13→17
7595 measured reflections	l = −10→10

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0915P)^2] where P = (Fo^2 + 2Fc^2)/3
2861 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.31 e Å^−3
6 restraints	Δρmin = −0.33 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
Cl1	0.18055 (5)	0.55707 (4)	0.40923 (7)	0.0671 (2)
O1	0.69423 (11)	0.64631 (10)	0.96925 (16)	0.0507 (4)
O2	0.58054 (11)	0.60055 (10)	1.20826 (14)	0.0477 (4)
O3	0.03375 (17)	0.14099 (16)	0.9084 (3)	0.0889 (6)
H3A	0.078 (3)	0.0935 (19)	0.913 (5)	0.133*
H3B	−0.009 (3)	0.144 (3)	0.982 (3)	0.133*
O4	0.01864 (15)	0.33585 (14)	0.8235 (3)	0.0771 (5)
H4A	−0.035 (2)	0.356 (2)	0.759 (4)	0.116*
H4B	0.021 (3)	0.2768 (8)	0.835 (4)	0.116*
N1	0.18185 (13)	0.47884 (12)	0.7824 (2)	0.0505 (4)
H1A	0.1746	0.5059	0.6848	0.076*
H1B	0.1368	0.4264	0.7827	0.076*
H1C	0.2555	0.4617	0.8070	0.076*
C1	0.33476 (16)	0.64376 (12)	0.9030 (2)	0.0445 (4)
C2	0.39437 (16)	0.62112 (13)	1.0513 (2)	0.0424 (4)
H2	0.3530	0.6060	1.1391	0.051*
C3	0.51381 (15)	0.62097 (12)	1.0688 (2)	0.0378 (4)
C4	0.57639 (15)	0.64498 (12)	0.9373 (2)	0.0388 (4)
C5	0.51805 (17)	0.66520 (14)	0.7900 (2)	0.0455 (4)
H5	0.5592	0.6795	0.7017	0.055*
C6	0.39767 (17)	0.66420 (14)	0.7733 (2)	0.0495 (5)
H6	0.3587	0.6775	0.6732	0.059*
C7	0.20417 (17)	0.64754 (15)	0.8852 (3)	0.0583 (6)
H7A	0.1791	0.6737	0.7796	0.070*
H7B	0.1783	0.6919	0.9654	0.070*
C8	0.14611 (17)	0.54999 (14)	0.9039 (3)	0.0528 (5)
H8A	0.1669	0.5250	1.0116	0.063*
H8B	0.0625	0.5581	0.8909	0.063*
C9	0.7609 (2)	0.6788 (2)	0.8439 (3)	0.0698 (7)
H9A	0.7507	0.6348	0.7542	0.105*
H9B	0.8414	0.6811	0.8830	0.105*
H9C	0.7355	0.7426	0.8099	0.105*
C10	0.52209 (19)	0.58043 (17)	1.3490 (2)	0.0559 (5)
H10A	0.4782	0.6365	1.3760	0.084*
H10B	0.5781	0.5650	1.4372	0.084*
H10C	0.4706	0.5263	1.3282	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0574 (4)	0.0773 (4)	0.0677 (4)	0.0035 (2)	0.0115 (3)	0.0049 (3)
O1	0.0389 (7)	0.0661 (9)	0.0482 (8)	−0.0011 (6)	0.0099 (6)	0.0112 (6)
O2	0.0467 (7)	0.0618 (8)	0.0353 (7)	0.0011 (6)	0.0083 (5)	0.0076 (6)
O3	0.0759 (13)	0.0852 (13)	0.1098 (16)	0.0060 (10)	0.0322 (11)	0.0236 (12)
O4	0.0576 (10)	0.0692 (11)	0.1028 (14)	−0.0154 (8)	−0.0035 (9)	0.0102 (10)
N1	0.0392 (8)	0.0522 (9)	0.0591 (10)	−0.0040 (7)	−0.0007 (7)	0.0075 (8)
C1	0.0425 (10)	0.0339 (9)	0.0567 (11)	−0.0002 (7)	0.0023 (8)	−0.0017 (8)
C2	0.0432 (10)	0.0389 (9)	0.0466 (10)	−0.0005 (7)	0.0115 (8)	−0.0011 (7)
C3	0.0417 (9)	0.0343 (8)	0.0380 (9)	−0.0002 (7)	0.0067 (7)	−0.0001 (7)
C4	0.0388 (9)	0.0364 (9)	0.0419 (9)	−0.0008 (7)	0.0072 (7)	−0.0005 (7)
C5	0.0519 (11)	0.0459 (10)	0.0393 (10)	−0.0055 (8)	0.0078 (8)	0.0026 (7)
C6	0.0529 (11)	0.0451 (10)	0.0490 (11)	−0.0041 (8)	−0.0042 (9)	0.0077 (8)
C7	0.0427 (11)	0.0485 (11)	0.0828 (15)	0.0066 (9)	0.0001 (10)	0.0025 (10)
C8	0.0358 (9)	0.0588 (12)	0.0642 (13)	0.0003 (8)	0.0070 (8)	0.0035 (10)
C9	0.0468 (12)	0.1016 (19)	0.0637 (14)	−0.0055 (12)	0.0199 (10)	0.0182 (13)
C10	0.0677 (13)	0.0637 (12)	0.0381 (10)	−0.0037 (10)	0.0142 (9)	0.0097 (9)

Geometric parameters (Å, º)

O1—C4	1.366 (2)	C3—C4	1.402 (2)
O1—C9	1.421 (2)	C4—C5	1.375 (3)
O2—C3	1.366 (2)	C5—C6	1.387 (3)
O2—C10	1.428 (2)	C5—H5	0.9300
O3—H3A	0.83 (3)	C6—H6	0.9300
O3—H3B	0.82 (3)	C7—C8	1.515 (3)
O4—H4A	0.83 (3)	C7—H7A	0.9700
O4—H4B	0.818 (12)	C7—H7B	0.9700
N1—C8	1.491 (3)	C8—H8A	0.9700
N1—H1A	0.8900	C8—H8B	0.9700
N1—H1B	0.8900	C9—H9A	0.9600
N1—H1C	0.8900	C9—H9B	0.9600
C1—C6	1.381 (3)	C9—H9C	0.9600
C1—C2	1.395 (3)	C10—H10A	0.9600
C1—C7	1.506 (3)	C10—H10B	0.9600
C2—C3	1.376 (3)	C10—H10C	0.9600
C2—H2	0.9300
C4—O1—C9	117.18 (15)	C1—C6—H6	119.5
C3—O2—C10	117.58 (15)	C5—C6—H6	119.5
H3A—O3—H3B	114 (2)	C1—C7—C8	114.14 (16)
H4A—O4—H4B	115 (2)	C1—C7—H7A	108.7
C8—N1—H1A	109.5	C8—C7—H7A	108.7
C8—N1—H1B	109.5	C1—C7—H7B	108.7
H1A—N1—H1B	109.5	C8—C7—H7B	108.7
C8—N1—H1C	109.5	H7A—C7—H7B	107.6
H1A—N1—H1C	109.5	N1—C8—C7	111.16 (17)
H1B—N1—H1C	109.5	N1—C8—H8A	109.4
C6—C1—C2	118.84 (17)	C7—C8—H8A	109.4
C6—C1—C7	120.52 (19)	N1—C8—H8B	109.4
C2—C1—C7	120.62 (18)	C7—C8—H8B	109.4
C3—C2—C1	120.56 (17)	H8A—C8—H8B	108.0
C3—C2—H2	119.7	O1—C9—H9A	109.5
C1—C2—H2	119.7	O1—C9—H9B	109.5
O2—C3—C2	125.34 (16)	H9A—C9—H9B	109.5
O2—C3—C4	114.77 (15)	O1—C9—H9C	109.5
C2—C3—C4	119.88 (16)	H9A—C9—H9C	109.5
O1—C4—C5	125.11 (16)	H9B—C9—H9C	109.5
O1—C4—C3	115.15 (15)	O2—C10—H10A	109.5
C5—C4—C3	119.74 (17)	O2—C10—H10B	109.5
C4—C5—C6	119.87 (18)	H10A—C10—H10B	109.5
C4—C5—H5	120.1	O2—C10—H10C	109.5
C6—C5—H5	120.1	H10A—C10—H10C	109.5
C1—C6—C5	121.06 (18)	H10B—C10—H10C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2^i	0.89	2.10	2.952 (2)	161
N1—H1C···O1^i	0.89	2.41	2.962 (2)	120
O3—H3A···Cl1^ii	0.83 (3)	2.39 (3)	3.211 (2)	172 (4)
O3—H3B···Cl1^iii	0.82 (3)	2.55 (3)	3.229 (2)	141 (4)
O4—H4A···Cl1^iv	0.83 (3)	2.42 (3)	3.233 (2)	169 (3)
N1—H1B···O4	0.89	1.90	2.768 (2)	164
N1—H1A···Cl1	0.89	2.40	3.2833 (19)	170

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, −y+1/2, z+1/2; (iii) −x, y−1/2, −z+3/2; (iv) −x, −y+1, −z+1.