N-(Di­cyclo­propyl­methylamino)-4,5-di­hydro-1,3-oxazolium dihydrogenphosphate

The title compound, C₁₀H₁₇N₂O⁺·H₂PO₄⁻, consists of a rilmenidine cation and a phosphate anion. In the solid state, the inversion-related phosphate anions are linked by O—H...O hydrogen bonds to form a chain along the a axis. The cations are connected to the chain via N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.084
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293

   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

   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
   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: 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: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C10H17N2O^+·H2O4P^−	Z = 2
Mr = 278.24	F(000) = 296
Triclinic, P1	Dx = 1.376 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3212 (8) Å	Cell parameters from 2726 reflections
b = 8.9609 (9) Å	θ = 2.4–28.6°
c = 9.8813 (10) Å	µ = 0.22 mm^−1
α = 97.070 (2)°	T = 293 K
β = 101.475 (2)°	Block, white
γ = 108.355 (2)°	0.48 × 0.48 × 0.46 mm
V = 671.54 (12) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2120 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.011
Graphite monochromator	θmax = 25.1°, θmin = 2.2°
φ and ω scans	h = −9→8
3425 measured reflections	k = −10→10
2342 independent reflections	l = −11→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 0.1859P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2342 reflections	Δρmax = 0.17 e Å^−3
180 parameters	Δρmin = −0.25 e Å^−3
1 restraint	Extinction correction: SHELXTL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.041 (4)

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
P	0.74068 (5)	0.45733 (5)	0.01745 (4)	0.03961 (16)
O3	0.64830 (15)	−0.04662 (12)	0.28368 (11)	0.0454 (3)
N1	0.73497 (19)	0.07777 (17)	0.11883 (14)	0.0458 (3)
N6	0.61067 (18)	0.19272 (16)	0.27686 (14)	0.0430 (3)
C2	0.66448 (19)	0.08108 (17)	0.22573 (15)	0.0375 (3)
C4	0.7392 (2)	−0.13967 (19)	0.21748 (18)	0.0515 (4)
H4A	0.6697	−0.2532	0.1939	0.062*
H4B	0.8517	−0.1242	0.2795	0.062*
C5	0.7619 (2)	−0.07433 (19)	0.08626 (17)	0.0473 (4)
H5A	0.8781	−0.0583	0.0729	0.057*
H5B	0.6752	−0.1442	0.0031	0.057*
C7	0.5272 (2)	0.18359 (18)	0.39558 (15)	0.0405 (3)
H7	0.4717	0.0700	0.3970	0.049*
C8	0.3856 (2)	0.2551 (2)	0.36854 (17)	0.0470 (4)
H8	0.4252	0.3711	0.3724	0.056*
C9	0.2269 (3)	0.1873 (3)	0.4218 (2)	0.0626 (5)
H9A	0.2200	0.0975	0.4688	0.075*
H9B	0.1749	0.2613	0.4585	0.075*
C10	0.2142 (2)	0.1593 (3)	0.2678 (2)	0.0636 (5)
H10A	0.1995	0.0523	0.2212	0.076*
H10B	0.1544	0.2160	0.2109	0.076*
C11	0.6560 (2)	0.2629 (2)	0.53664 (17)	0.0491 (4)
H11	0.6030	0.2559	0.6169	0.059*
C12	0.8388 (3)	0.2615 (2)	0.5689 (2)	0.0673 (5)
H12A	0.8884	0.2494	0.6626	0.081*
H12B	0.8761	0.2118	0.4939	0.081*
C13	0.8054 (3)	0.4134 (2)	0.5545 (2)	0.0688 (5)
H13A	0.8353	0.4937	0.6395	0.083*
H13B	0.8230	0.4561	0.4709	0.083*
O1	0.81915 (15)	0.33081 (13)	−0.01304 (13)	0.0498 (3)
O2	0.62255 (15)	0.42479 (14)	0.11584 (12)	0.0506 (3)
O4	0.63681 (17)	0.47379 (17)	−0.12690 (13)	0.0576 (3)
O5	0.88770 (17)	0.62380 (14)	0.08172 (15)	0.0576 (3)
H1N	0.756 (2)	0.154 (2)	0.073 (2)	0.059 (5)*
H6N	0.620 (2)	0.270 (2)	0.2336 (19)	0.050 (5)*
H4O	0.560 (2)	0.509 (3)	−0.118 (2)	0.081 (7)*
H5O	0.978 (3)	0.633 (2)	0.058 (2)	0.066 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.0400 (2)	0.0429 (2)	0.0497 (3)	0.02245 (18)	0.02236 (18)	0.01948 (18)
O3	0.0597 (7)	0.0406 (6)	0.0494 (6)	0.0252 (5)	0.0260 (5)	0.0174 (5)
N1	0.0598 (9)	0.0440 (7)	0.0472 (7)	0.0251 (7)	0.0267 (7)	0.0177 (6)
N6	0.0551 (8)	0.0427 (7)	0.0471 (7)	0.0265 (6)	0.0252 (6)	0.0214 (6)
C2	0.0392 (8)	0.0379 (7)	0.0387 (8)	0.0150 (6)	0.0119 (6)	0.0120 (6)
C4	0.0672 (11)	0.0421 (9)	0.0585 (10)	0.0287 (8)	0.0281 (9)	0.0126 (7)
C5	0.0545 (10)	0.0445 (8)	0.0472 (9)	0.0205 (7)	0.0184 (7)	0.0060 (7)
C7	0.0464 (8)	0.0420 (8)	0.0436 (8)	0.0209 (7)	0.0209 (7)	0.0166 (6)
C8	0.0523 (9)	0.0520 (9)	0.0514 (9)	0.0287 (8)	0.0227 (7)	0.0205 (7)
C9	0.0619 (11)	0.0834 (13)	0.0681 (12)	0.0411 (10)	0.0357 (10)	0.0339 (10)
C10	0.0560 (11)	0.0852 (14)	0.0596 (11)	0.0325 (10)	0.0158 (9)	0.0277 (10)
C11	0.0533 (10)	0.0536 (9)	0.0468 (9)	0.0221 (8)	0.0182 (7)	0.0142 (7)
C12	0.0565 (11)	0.0719 (13)	0.0684 (12)	0.0280 (10)	0.0019 (9)	0.0033 (10)
C13	0.0695 (13)	0.0556 (11)	0.0729 (13)	0.0137 (10)	0.0168 (10)	0.0061 (9)
O1	0.0507 (7)	0.0437 (6)	0.0726 (8)	0.0249 (5)	0.0333 (6)	0.0236 (5)
O2	0.0525 (7)	0.0647 (7)	0.0605 (7)	0.0361 (6)	0.0323 (6)	0.0350 (6)
O4	0.0572 (7)	0.0862 (9)	0.0516 (7)	0.0427 (7)	0.0259 (6)	0.0276 (6)
O5	0.0467 (7)	0.0495 (7)	0.0825 (9)	0.0206 (6)	0.0297 (6)	0.0022 (6)

Geometric parameters (Å, º)

P—O1	1.5043 (11)	C7—H7	0.98
P—O2	1.5053 (11)	C8—C10	1.488 (3)
P—O5	1.5599 (13)	C8—C9	1.497 (2)
P—O4	1.5637 (13)	C8—H8	0.98
O3—C2	1.3230 (17)	C9—C10	1.489 (3)
O3—C4	1.4679 (18)	C9—H9A	0.97
N1—C2	1.3079 (19)	C9—H9B	0.97
N1—C5	1.457 (2)	C10—H10A	0.97
N1—H1N	0.85 (2)	C10—H10B	0.97
N6—C2	1.3055 (19)	C11—C13	1.482 (3)
N6—C7	1.4755 (19)	C11—C12	1.496 (3)
N6—H6N	0.85 (2)	C11—H11	0.98
C4—C5	1.508 (2)	C12—C13	1.491 (3)
C4—H4A	0.97	C12—H12A	0.97
C4—H4B	0.97	C12—H12B	0.97
C5—H5A	0.97	C13—H13A	0.97
C5—H5B	0.97	C13—H13B	0.97
C7—C8	1.504 (2)	O4—H4O	0.812 (10)
C7—C11	1.509 (2)	O5—H5O	0.82 (2)
O1—P—O2	114.96 (6)	C9—C8—C7	118.09 (14)
O1—P—O5	110.43 (7)	C10—C8—H8	115.9
O2—P—O5	107.70 (7)	C9—C8—H8	115.9
O1—P—O4	107.33 (7)	C7—C8—H8	115.9
O2—P—O4	109.72 (7)	C10—C9—C8	59.81 (12)
O5—P—O4	106.37 (8)	C10—C9—H9A	117.8
C2—O3—C4	107.31 (12)	C8—C9—H9A	117.8
C2—N1—C5	110.63 (13)	C10—C9—H9B	117.8
C2—N1—H1N	123.2 (13)	C8—C9—H9B	117.8
C5—N1—H1N	126.1 (13)	H9A—C9—H9B	114.9
C2—N6—C7	123.53 (12)	C8—C10—C9	60.36 (12)
C2—N6—H6N	115.5 (12)	C8—C10—H10A	117.7
C7—N6—H6N	120.8 (12)	C9—C10—H10A	117.7
N6—C2—N1	127.36 (13)	C8—C10—H10B	117.7
N6—C2—O3	119.44 (13)	C9—C10—H10B	117.7
N1—C2—O3	113.20 (13)	H10A—C10—H10B	114.9
O3—C4—C5	104.29 (12)	C13—C11—C12	60.08 (13)
O3—C4—H4A	110.9	C13—C11—C7	121.65 (15)
C5—C4—H4A	110.9	C12—C11—C7	122.53 (15)
O3—C4—H4B	110.9	C13—C11—H11	114.1
C5—C4—H4B	110.9	C12—C11—H11	114.1
H4A—C4—H4B	108.9	C7—C11—H11	114.1
N1—C5—C4	101.11 (12)	C13—C12—C11	59.50 (13)
N1—C5—H5A	111.6	C13—C12—H12A	117.8
C4—C5—H5A	111.6	C11—C12—H12A	117.8
N1—C5—H5B	111.6	C13—C12—H12B	117.8
C4—C5—H5B	111.6	C11—C12—H12B	117.8
H5A—C5—H5B	109.4	H12A—C12—H12B	115.0
N6—C7—C8	108.52 (12)	C11—C13—C12	60.42 (13)
N6—C7—C11	113.00 (13)	C11—C13—H13A	117.7
C8—C7—C11	111.59 (13)	C12—C13—H13A	117.7
N6—C7—H7	107.8	C11—C13—H13B	117.7
C8—C7—H7	107.8	C12—C13—H13B	117.7
C11—C7—H7	107.8	H13A—C13—H13B	114.9
C10—C8—C9	59.83 (13)	P—O4—H4O	112.3 (17)
C10—C8—C7	119.62 (15)	P—O5—H5O	113.3 (15)
C7—N6—C2—N1	177.96 (15)	C11—C7—C8—C10	−156.59 (15)
C7—N6—C2—O3	−1.6 (2)	N6—C7—C8—C9	147.66 (15)
C5—N1—C2—N6	−174.57 (15)	C11—C7—C8—C9	−87.19 (19)
C5—N1—C2—O3	4.99 (19)	C7—C8—C9—C10	−109.74 (18)
C4—O3—C2—N6	−172.80 (14)	C7—C8—C10—C9	107.21 (17)
C4—O3—C2—N1	7.60 (18)	N6—C7—C11—C13	38.1 (2)
C2—O3—C4—C5	−16.29 (17)	C8—C7—C11—C13	−84.49 (19)
C2—N1—C5—C4	−14.60 (18)	N6—C7—C11—C12	−34.3 (2)
O3—C4—C5—N1	17.88 (16)	C8—C7—C11—C12	−156.92 (16)
C2—N6—C7—C8	−142.91 (15)	C7—C11—C12—C13	110.56 (19)
C2—N6—C7—C11	92.78 (18)	C7—C11—C13—C12	−111.96 (18)
N6—C7—C8—C10	78.27 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.85 (2)	1.87 (2)	2.724 (2)	175 (2)
N6—H6N···O2	0.85 (2)	1.92 (2)	2.759 (2)	173 (2)
O4—H4O···O2^i	0.81 (1)	1.80 (1)	2.608 (2)	175 (2)
O5—H5O···O1^ii	0.82 (2)	1.77 (2)	2.584 (2)	175 (2)

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