L-Tyrosinamide hydro­chloride monohydrate

Cations of the title compound, 1-carbamoyl-2-(4-hydroxy­phen­yl)ethyl­ammonium chloride monohydrate, C₉H₁₃N₂O₂⁺·Cl⁻·H₂O, are connected by inter­molecular N—H...O [N...O = 2.905 (3) Å] hydrogen bonds between the amide and 4-hydr­oxy functions into helical chains propagating along the [010] axis. The Cl⁻ ions and water O atom participate in a complex pattern of hydrogen bonds to link these ribbons into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.079
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3
PLAT731_ALERT_1_C Bond    Calc     0.83(3), Rep   0.833(10) ......       3.00 su-Rat
              OW   -HW1     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.83(3), Rep   0.833(10) ......       3.00 su-Rat
              O1#  -H1#     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.35(3), Rep   2.350(14) ......       2.14 su-Rat
              H1#  -CL1     1.555   2.645

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               2136
           Count of symmetry unique reflns         1858
           Completeness (_total/calc)            114.96%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       278
           Fraction of Friedel pairs measured     0.150
           Are heavy atom types Z>Si present        yes

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

   6 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: R3m/V (Siemens, 1989); cell refinement: R3m/V; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.

1-carbamoyl-2-(4-hydroxyphenyl)ethylammonium chloride monohydrate

Crystal data

C9H13N2O2^+·Cl^−·H2O	F(000) = 248
Mr = 234.68	Dx = 1.332 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 23 reflections
a = 7.3671 (17) Å	θ = 7.5–12.5°
b = 6.020 (2) Å	µ = 0.32 mm^−1
c = 13.689 (3) Å	T = 293 K
β = 105.551 (12)°	Block, colourless
V = 584.9 (3) Å^3	0.59 × 0.46 × 0.43 mm
Z = 2

Data collection

Siemens P4 four-circle diffractometer	1966 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
Graphite monochromator	θmax = 30.0°, θmin = 3.7°
Profile fitted ω scans	h = −1→10
Absorption correction: ψ scan (SHELXTL-Plus; Sheldrick, 1998)	k = −8→8
Tmin = 0.790, Tmax = 0.875	l = −19→18
2595 measured reflections	3 standard reflections every 100 reflections
2136 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0422P)^2 + 0.0448P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.079	(Δ/σ)max = 0.003
S = 1.04	Δρmax = 0.23 e Å^−3
2136 reflections	Δρmin = −0.20 e Å^−3
146 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.150 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 293 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.04 (6)

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	0.17138 (6)	0.97493 (8)	0.15281 (3)	0.04233 (13)
C1	0.7308 (2)	0.3821 (3)	0.16898 (11)	0.0369 (4)
O1	0.6515 (2)	0.2432 (3)	0.10703 (13)	0.0660 (5)
N1	0.9148 (2)	0.3822 (3)	0.21385 (12)	0.0451 (4)
H1	0.9855	0.2801	0.1998	0.054*
H11	0.9631	0.4842	0.2569	0.054*
C2	0.6153 (2)	0.5671 (3)	0.19985 (11)	0.0333 (3)
H2	0.6987	0.6865	0.2342	0.040*
N2	0.4848 (2)	0.6523 (3)	0.10422 (11)	0.0404 (4)
H21	0.5515	0.7120	0.0655	0.048*
H22	0.4094	0.7549	0.1190	0.048*
H23	0.4158	0.5406	0.0711	0.048*
C3	0.4984 (2)	0.4776 (4)	0.26913 (11)	0.0399 (3)
H31	0.4045	0.5874	0.2735	0.048*
H32	0.4325	0.3445	0.2390	0.048*
C11	0.6174 (2)	0.4236 (3)	0.37527 (11)	0.0351 (4)
C12	0.7114 (3)	0.2220 (4)	0.39778 (13)	0.0405 (4)
H12	0.7015	0.1174	0.3466	0.049*
C13	0.8198 (3)	0.1738 (3)	0.49542 (14)	0.0394 (4)
H13	0.8827	0.0387	0.5093	0.047*
C14	0.8332 (2)	0.3282 (3)	0.57149 (12)	0.0359 (4)
O4	0.9428 (2)	0.2751 (3)	0.66704 (9)	0.0536 (4)
H4	0.9406	0.3779	0.7060	0.080*
C15	0.7414 (2)	0.5304 (3)	0.55156 (12)	0.0374 (4)
H15	0.7512	0.6339	0.6031	0.045*
C16	0.6339 (2)	0.5771 (3)	0.45320 (12)	0.0364 (3)
H16	0.5723	0.7130	0.4395	0.044*
OW	0.7644 (2)	0.8168 (3)	0.00989 (11)	0.0507 (4)
HW1	0.804 (4)	0.736 (6)	−0.029 (2)	0.091 (11)*
HW2	0.862 (3)	0.867 (5)	0.0496 (17)	0.063 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0431 (2)	0.0426 (2)	0.04370 (19)	0.0094 (2)	0.01584 (14)	0.0028 (2)
C1	0.0370 (7)	0.0413 (9)	0.0290 (6)	0.0089 (8)	0.0028 (5)	−0.0048 (7)
O1	0.0543 (8)	0.0669 (11)	0.0617 (9)	0.0188 (8)	−0.0106 (7)	−0.0369 (9)
N1	0.0360 (7)	0.0491 (9)	0.0462 (7)	0.0112 (7)	0.0043 (6)	−0.0114 (8)
C2	0.0327 (6)	0.0376 (8)	0.0273 (6)	0.0065 (7)	0.0041 (5)	−0.0035 (6)
N2	0.0424 (7)	0.0477 (9)	0.0299 (6)	0.0152 (7)	0.0079 (5)	0.0029 (6)
C3	0.0349 (6)	0.0514 (10)	0.0318 (6)	0.0058 (10)	0.0059 (5)	0.0012 (9)
C11	0.0345 (7)	0.0402 (10)	0.0313 (6)	0.0039 (7)	0.0101 (5)	0.0031 (6)
C12	0.0519 (10)	0.0358 (9)	0.0362 (7)	0.0053 (8)	0.0159 (7)	−0.0022 (8)
C13	0.0451 (9)	0.0351 (9)	0.0413 (8)	0.0105 (8)	0.0174 (7)	0.0065 (7)
C14	0.0332 (7)	0.0431 (9)	0.0328 (7)	0.0053 (7)	0.0111 (6)	0.0068 (7)
O4	0.0613 (8)	0.0628 (11)	0.0333 (6)	0.0229 (8)	0.0068 (5)	0.0083 (7)
C15	0.0411 (8)	0.0380 (9)	0.0334 (7)	0.0045 (7)	0.0103 (6)	−0.0025 (7)
C16	0.0378 (7)	0.0342 (8)	0.0369 (7)	0.0075 (7)	0.0095 (6)	0.0032 (7)
OW	0.0448 (7)	0.0572 (9)	0.0468 (7)	−0.0018 (7)	0.0068 (6)	−0.0149 (7)

Geometric parameters (Å, º)

C1—O1	1.222 (2)	C11—C12	1.390 (3)
C1—N1	1.330 (2)	C11—C16	1.392 (2)
C1—C2	1.529 (2)	C12—C13	1.392 (3)
N1—H1	0.8600	C12—H12	0.9300
N1—H11	0.8600	C13—C14	1.380 (3)
C2—N2	1.492 (2)	C13—H13	0.9300
C2—C3	1.540 (2)	C14—O4	1.378 (2)
C2—H2	0.9800	C14—C15	1.383 (3)
N2—H21	0.8900	O4—H4	0.8200
N2—H22	0.8900	C15—C16	1.396 (2)
N2—H23	0.8900	C15—H15	0.9300
C3—C11	1.518 (2)	C16—H16	0.9300
C3—H31	0.9700	OW—HW1	0.833 (10)
C3—H32	0.9700	OW—HW2	0.830 (10)
O1—C1—N1	123.99 (18)	C2—C3—H32	109.0
O1—C1—C2	119.50 (15)	H31—C3—H32	107.8
N1—C1—C2	116.50 (16)	C12—C11—C16	118.29 (15)
C1—N1—H1	120.0	C12—C11—C3	121.66 (17)
C1—N1—H11	120.0	C16—C11—C3	120.05 (18)
H1—N1—H11	120.0	C11—C12—C13	121.22 (17)
N2—C2—C1	106.46 (12)	C11—C12—H12	119.4
N2—C2—C3	108.99 (13)	C13—C12—H12	119.4
C1—C2—C3	111.11 (17)	C14—C13—C12	119.41 (18)
N2—C2—H2	110.1	C14—C13—H13	120.3
C1—C2—H2	110.1	C12—C13—H13	120.3
C3—C2—H2	110.1	O4—C14—C13	117.73 (18)
C2—N2—H21	109.5	O4—C14—C15	121.49 (17)
C2—N2—H22	109.5	C13—C14—C15	120.77 (15)
H21—N2—H22	109.5	C14—O4—H4	109.5
C2—N2—H23	109.5	C14—C15—C16	119.25 (16)
H21—N2—H23	109.5	C14—C15—H15	120.4
H22—N2—H23	109.5	C16—C15—H15	120.4
C11—C3—C2	112.92 (13)	C11—C16—C15	121.06 (17)
C11—C3—H31	109.0	C11—C16—H16	119.5
C2—C3—H31	109.0	C15—C16—H16	119.5
C11—C3—H32	109.0	HW1—OW—HW2	104 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···Cl1^i	0.82	2.37	3.0576 (16)	142
N1—H11···O4^ii	0.86	2.06	2.905 (3)	167
N2—H22···Cl1	0.89	2.34	3.2206 (17)	170
N2—H21···OW	0.89	2.02	2.884 (2)	164
N2—H23···OW^iii	0.89	2.00	2.890 (3)	173
OW—HW1···Cl1^iii	0.83 (1)	2.35 (1)	3.1601 (17)	164 (3)
OW—HW2···Cl1^iv	0.83 (1)	2.43 (1)	3.2523 (16)	171 (3)

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