Tetra­hydro­pyrimidin-2-ylidene­ammonium camphor-10-sulfonate

Harrison, W.T.A.

doi:10.1107/S160053680704442X

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Tetrahydropyrimidin-2-ylideneammonium camphor-10-sulfonate

W. T. A. Harrison

In the title molecular salt (alternative name: tetrahydropyrimidin-2-ylideneammonium 2-oxobornane-10-sulfonate), C₄H₁₀N₃⁺·C₁₀H₁₅O₄S⁻, the cation and anion interact by way of N—H

O hydrogen bonds, leading to chains propagating in the polar [010] direction containing R²₂(8) supramolecular loops.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704442X/rn2027sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680704442X/rn2027Isup2.hkl Contains datablock I

CCDC reference: 663768

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.036
wR factor = 0.097
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.99 Deg.
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         90 PerFi

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           24.99
           From the CIF: _reflns_number_total               3003
           Count of symmetry unique reflns         1662
           Completeness (_total/calc)            180.69%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1341
           Fraction of Friedel pairs measured     0.807
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

Comment top

The title compound, (I), is a molecular salt (Fig. 1). The C—N bond lengths in the cation [C11—N2 = 1.319 (5) Å, C11—N1 = 1.330 (3) Å, C11—N3 = 1.332 (5) Å] indicate delocalization of the electrons in the nominal C—N single bonds and C═N⁺ double bond (see scheme) in a similar fashion to that seen in the CN₃H₆⁺ guanidinium cation. The bond angle sum at C11 is exactly 360°. The conformation of the six-membered ring of the cation is well described as an envelope, with C13 displaced by 0.632 (4) Å from C11/C12/C14/N2/N3 (r.m.s. deviation for these atoms = 0.002 Å). The configurations of the chiral carbon atoms in the camphor sulfonate anion are: C2 R and C5 S. Otherwise, (I) displays normal geometrical parameters (Allen et al., 1995).

In the crystal of (I), the components interact by way of N—H···O hydrogen bonds (Table 1) leading to infinite chains propagating in [010], with every cation and anion linked by two N—H···O bonds (Fig. 2), resulting in graph-theory (Bernstein et al., 1995) R²₂(8) loops.

Related literature top

For background, see: Bernstein et al. (1995). For reference structural data, see: Allen et al. (1995).

Experimental top

Aqueous solutions of tetrahydro-pyrimidin-2-ylidene-amine and camphor-10-sulfonic acid were mixed in stoichiometric quantities leading to a clear solution. Colourless faceted chunks of (I) grew over a few days as the water slowly evaporated.

Structure description top

For background, see: Bernstein et al. (1995). For reference structural data, see: Allen et al. (1995).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. The molecular structure of (I) (40% displacement ellipsoids, arbitrary spheres for the H atoms, hydrogen bonds indicated by double dashed lines).
	Fig. 2. Detail of (I) showing an [010] hydrogen-bonded chain containing R²₂(8) loops. Atoms marked with a * suffix are at the symmetry position (x, y - 1, z).

Tetrahydropyrimidin-2-ylideneammonium 2-oxobornane-10-sulfonate top

Crystal data top

C₄H₁₀N₃⁺·C₁₀H₁₅O₄S⁻	F(000) = 356
M_r = 331.43	D_x = 1.267 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3004 reflections
a = 7.4207 (4) Å	θ = 2.8–25.0°
b = 7.3115 (4) Å	µ = 0.21 mm⁻¹
c = 16.421 (1) Å	T = 293 K
β = 102.899 (1)°	Faceted chunk, colourless
V = 868.46 (9) Å³	0.32 × 0.26 × 0.17 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD diffractometer	3003 independent reflections
Radiation source: fine-focus sealed tube	2630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→8
T_min = 0.860, T_max = 0.967	k = −8→8
5301 measured reflections	l = −16→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0532P)² + 0.0964P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3003 reflections	Δρ_max = 0.15 e Å⁻³
214 parameters	Δρ_min = −0.30 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 1341 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.17 (9)

Crystal data top

C₄H₁₀N₃⁺·C₁₀H₁₅O₄S⁻	V = 868.46 (9) Å³
M_r = 331.43	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.4207 (4) Å	µ = 0.21 mm⁻¹
b = 7.3115 (4) Å	T = 293 K
c = 16.421 (1) Å	0.32 × 0.26 × 0.17 mm
β = 102.899 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3003 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2630 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.967	R_int = 0.017
5301 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.097	Δρ_max = 0.15 e Å⁻³
S = 1.09	Δρ_min = −0.30 e Å⁻³
3003 reflections	Absolute structure: Flack (1983), with 1341 Friedel pairs
214 parameters	Absolute structure parameter: 0.17 (9)
1 restraint

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
C1	0.5794 (3)	0.3098 (6)	0.20808 (13)	0.0443 (5)
H1A	0.4756	0.2258	0.1970	0.053*
H1B	0.5307	0.4301	0.1904	0.053*
C2	0.7072 (3)	0.2553 (3)	0.15159 (16)	0.0429 (6)
C3	0.6026 (4)	0.2795 (4)	0.06007 (18)	0.0592 (9)
C4	0.7455 (5)	0.2783 (7)	0.00768 (19)	0.0804 (13)
H41	0.7483	0.3941	−0.0209	0.096*
H42	0.7233	0.1802	−0.0331	0.096*
C5	0.9240 (5)	0.2470 (4)	0.07361 (19)	0.0636 (8)
H51	1.0374	0.2795	0.0557	0.062 (8)*
C6	0.9151 (5)	0.0456 (5)	0.1020 (2)	0.0736 (10)
H61	0.8800	−0.0355	0.0543	0.088*
H62	1.0330	0.0063	0.1359	0.088*
C7	0.7654 (5)	0.0506 (4)	0.1535 (2)	0.0567 (7)
H71	0.8148	0.0100	0.2104	0.068*
H72	0.6612	−0.0263	0.1285	0.068*
C8	0.8908 (4)	0.3566 (4)	0.14960 (17)	0.0496 (8)
C9	0.8664 (5)	0.5612 (4)	0.1348 (3)	0.0729 (10)
H91	0.9728	0.6098	0.1181	0.109*
H92	0.8529	0.6199	0.1854	0.109*
H93	0.7581	0.5833	0.0916	0.109*
C10	1.0493 (3)	0.3306 (7)	0.22651 (17)	0.0639 (7)
H101	1.1640	0.3649	0.2130	0.096*
H102	1.0550	0.2046	0.2434	0.096*
H103	1.0280	0.4059	0.2713	0.096*
S1	0.66387 (7)	0.31798 (11)	0.31831 (3)	0.03870 (15)
O1	0.7694 (3)	0.4848 (3)	0.33660 (15)	0.0523 (6)
O2	0.7726 (3)	0.1533 (3)	0.34393 (14)	0.0505 (6)
O3	0.4966 (2)	0.3208 (4)	0.35201 (10)	0.0505 (4)
O4	0.4382 (3)	0.2951 (6)	0.03598 (13)	0.0893 (8)
C11	0.4246 (3)	0.8182 (6)	0.38435 (16)	0.0498 (5)
C12	0.1889 (5)	0.6527 (5)	0.4365 (2)	0.0538 (9)
H12A	0.2267	0.6427	0.4969	0.065*
H12B	0.1168	0.5452	0.4156	0.065*
C13	0.0735 (3)	0.8206 (6)	0.41374 (18)	0.0586 (6)
H13A	−0.0258	0.8211	0.4435	0.070*
H13B	0.0185	0.8195	0.3543	0.070*
C14	0.1890 (4)	0.9908 (4)	0.4354 (2)	0.0505 (8)
H14A	0.1171	1.0976	0.4131	0.061*
H14B	0.2262	1.0039	0.4956	0.061*
N1	0.5722 (3)	0.8172 (6)	0.3510 (2)	0.0822 (9)
H1	0.629 (6)	0.699 (7)	0.345 (3)	0.099*
H2	0.627 (7)	0.906 (7)	0.350 (3)	0.099*
N2	0.3515 (4)	0.6619 (4)	0.4010 (2)	0.0517 (8)
H3	0.378 (4)	0.570 (5)	0.383 (2)	0.062*
N3	0.3521 (4)	0.9775 (4)	0.4001 (2)	0.0527 (8)
H4	0.408 (5)	1.070 (5)	0.394 (2)	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0366 (10)	0.0506 (13)	0.0443 (11)	0.0004 (17)	0.0063 (9)	−0.0012 (17)
C2	0.0437 (13)	0.0438 (14)	0.0405 (13)	0.0009 (10)	0.0080 (10)	−0.0017 (10)
C3	0.0616 (17)	0.063 (3)	0.0484 (15)	−0.0021 (15)	0.0024 (12)	−0.0016 (14)
C4	0.093 (2)	0.106 (4)	0.0437 (15)	−0.007 (2)	0.0184 (15)	−0.0050 (19)
C5	0.0656 (18)	0.077 (2)	0.0562 (17)	−0.0009 (15)	0.0305 (15)	0.0032 (15)
C6	0.095 (3)	0.065 (2)	0.073 (2)	0.012 (2)	0.045 (2)	−0.0148 (18)
C7	0.0696 (19)	0.0443 (16)	0.0607 (19)	−0.0002 (15)	0.0238 (15)	−0.0062 (14)
C8	0.0461 (13)	0.052 (2)	0.0529 (14)	0.0002 (12)	0.0152 (11)	0.0028 (12)
C9	0.080 (2)	0.0486 (19)	0.093 (3)	−0.0117 (18)	0.024 (2)	0.0163 (19)
C10	0.0382 (12)	0.089 (2)	0.0655 (16)	0.007 (2)	0.0128 (11)	0.001 (2)
S1	0.0374 (3)	0.0358 (3)	0.0450 (3)	0.0025 (4)	0.0135 (2)	−0.0019 (4)
O1	0.0490 (14)	0.0429 (12)	0.0678 (16)	−0.0062 (11)	0.0189 (11)	−0.0168 (11)
O2	0.0507 (14)	0.0494 (13)	0.0523 (13)	0.0151 (11)	0.0134 (11)	0.0076 (10)
O3	0.0512 (8)	0.0438 (8)	0.0642 (10)	0.0014 (14)	0.0293 (7)	−0.0024 (13)
O4	0.0631 (12)	0.134 (2)	0.0595 (12)	−0.004 (2)	−0.0109 (10)	−0.0016 (19)
C11	0.0422 (11)	0.0410 (11)	0.0669 (14)	−0.003 (2)	0.0134 (10)	−0.004 (2)
C12	0.054 (2)	0.053 (2)	0.057 (2)	−0.0091 (17)	0.0194 (17)	−0.0034 (17)
C13	0.0465 (12)	0.0590 (15)	0.0738 (16)	0.000 (2)	0.0210 (11)	−0.002 (2)
C14	0.047 (2)	0.045 (2)	0.060 (2)	0.0069 (15)	0.0136 (16)	−0.0022 (16)
N1	0.0653 (14)	0.0459 (13)	0.153 (3)	−0.001 (2)	0.0619 (16)	−0.001 (3)
N2	0.0480 (18)	0.0379 (17)	0.072 (2)	0.0020 (14)	0.0194 (15)	−0.0073 (14)
N3	0.051 (2)	0.0336 (16)	0.078 (2)	0.0030 (14)	0.0253 (16)	−0.0037 (14)

Geometric parameters (Å, º) top

C1—C2	1.520 (3)	C9—H93	0.9600
C1—S1	1.779 (2)	C10—H101	0.9600
C1—H1A	0.9700	C10—H102	0.9600
C1—H1B	0.9700	C10—H103	0.9600
C2—C3	1.540 (4)	S1—O1	1.444 (2)
C2—C7	1.556 (4)	S1—O2	1.458 (2)
C2—C8	1.558 (3)	S1—O3	1.4678 (14)
C3—O4	1.201 (3)	C11—N2	1.319 (5)
C3—C4	1.507 (4)	C11—N1	1.330 (3)
C4—C5	1.529 (5)	C11—N3	1.332 (5)
C4—H41	0.9700	C12—N2	1.454 (4)
C4—H42	0.9700	C12—C13	1.496 (5)
C5—C8	1.548 (4)	C12—H12A	0.9700
C5—C6	1.550 (5)	C12—H12B	0.9700
C5—H51	0.9800	C13—C14	1.508 (5)
C6—C7	1.540 (4)	C13—H13A	0.9700
C6—H61	0.9700	C13—H13B	0.9700
C6—H62	0.9700	C14—N3	1.458 (4)
C7—H71	0.9700	C14—H14A	0.9700
C7—H72	0.9700	C14—H14B	0.9700
C8—C9	1.520 (4)	N1—H1	0.98 (5)
C8—C10	1.533 (4)	N1—H2	0.77 (5)
C9—H91	0.9600	N2—H3	0.78 (4)
C9—H92	0.9600	N3—H4	0.81 (4)

C2—C1—S1	120.23 (15)	H91—C9—H92	109.5
C2—C1—H1A	107.3	C8—C9—H93	109.5
S1—C1—H1A	107.3	H91—C9—H93	109.5
C2—C1—H1B	107.3	H92—C9—H93	109.5
S1—C1—H1B	107.3	C8—C10—H101	109.5
H1A—C1—H1B	106.9	C8—C10—H102	109.5
C1—C2—C3	108.6 (2)	H101—C10—H102	109.5
C1—C2—C7	116.6 (2)	C8—C10—H103	109.5
C3—C2—C7	102.0 (2)	H101—C10—H103	109.5
C1—C2—C8	123.8 (2)	H102—C10—H103	109.5
C3—C2—C8	100.2 (2)	O1—S1—O2	113.46 (10)
C7—C2—C8	102.6 (2)	O1—S1—O3	112.00 (13)
O4—C3—C4	127.2 (3)	O2—S1—O3	111.28 (14)
O4—C3—C2	125.9 (3)	O1—S1—C1	106.94 (16)
C4—C3—C2	106.9 (2)	O2—S1—C1	108.20 (15)
C3—C4—C5	101.8 (2)	O3—S1—C1	104.38 (10)
C3—C4—H41	111.4	N2—C11—N1	119.7 (4)
C5—C4—H41	111.4	N2—C11—N3	120.9 (2)
C3—C4—H42	111.4	N1—C11—N3	119.4 (4)
C5—C4—H42	111.4	N2—C12—C13	110.0 (3)
H41—C4—H42	109.3	N2—C12—H12A	109.7
C4—C5—C8	103.0 (3)	C13—C12—H12A	109.7
C4—C5—C6	105.5 (3)	N2—C12—H12B	109.7
C8—C5—C6	103.0 (2)	C13—C12—H12B	109.7
C4—C5—H51	114.7	H12A—C12—H12B	108.2
C8—C5—H51	114.7	C12—C13—C14	110.76 (19)
C6—C5—H51	114.7	C12—C13—H13A	109.5
C7—C6—C5	103.1 (2)	C14—C13—H13A	109.5
C7—C6—H61	111.1	C12—C13—H13B	109.5
C5—C6—H61	111.1	C14—C13—H13B	109.5
C7—C6—H62	111.1	H13A—C13—H13B	108.1
C5—C6—H62	111.1	N3—C14—C13	109.3 (2)
H61—C6—H62	109.1	N3—C14—H14A	109.8
C6—C7—C2	104.0 (2)	C13—C14—H14A	109.8
C6—C7—H71	111.0	N3—C14—H14B	109.8
C2—C7—H71	111.0	C13—C14—H14B	109.8
C6—C7—H72	111.0	H14A—C14—H14B	108.3
C2—C7—H72	111.0	C11—N1—H1	118 (3)
H71—C7—H72	109.0	C11—N1—H2	120 (4)
C9—C8—C10	107.2 (3)	H1—N1—H2	120 (3)
C9—C8—C5	114.6 (3)	C11—N2—C12	122.7 (3)
C10—C8—C5	111.6 (3)	C11—N2—H3	121 (3)
C9—C8—C2	113.4 (2)	C12—N2—H3	114 (3)
C10—C8—C2	115.9 (2)	C11—N3—C14	122.9 (3)
C5—C8—C2	93.9 (2)	C11—N3—H4	118 (3)
C8—C9—H91	109.5	C14—N3—H4	119 (3)
C8—C9—H92	109.5

S1—C1—C2—C3	−174.3 (2)	C4—C5—C8—C2	55.4 (3)
S1—C1—C2—C7	71.4 (3)	C6—C5—C8—C2	−54.1 (3)
S1—C1—C2—C8	−57.5 (4)	C1—C2—C8—C9	−53.8 (3)
C1—C2—C3—O4	−16.5 (5)	C3—C2—C8—C9	66.8 (3)
C7—C2—C3—O4	107.2 (4)	C7—C2—C8—C9	171.7 (3)
C8—C2—C3—O4	−147.5 (4)	C1—C2—C8—C10	70.9 (3)
C1—C2—C3—C4	163.9 (3)	C3—C2—C8—C10	−168.5 (3)
C7—C2—C3—C4	−72.5 (3)	C7—C2—C8—C10	−63.6 (3)
C8—C2—C3—C4	32.8 (3)	C1—C2—C8—C5	−172.8 (2)
O4—C3—C4—C5	−177.9 (4)	C3—C2—C8—C5	−52.1 (2)
C2—C3—C4—C5	1.8 (4)	C7—C2—C8—C5	52.7 (2)
C3—C4—C5—C8	−36.4 (3)	C2—C1—S1—O1	77.3 (3)
C3—C4—C5—C6	71.2 (3)	C2—C1—S1—O2	−45.2 (3)
C4—C5—C6—C7	−71.9 (3)	C2—C1—S1—O3	−163.9 (3)
C8—C5—C6—C7	35.8 (3)	N2—C12—C13—C14	−51.8 (3)
C5—C6—C7—C2	−1.5 (3)	C12—C13—C14—N3	51.3 (3)
C1—C2—C7—C6	−171.4 (2)	N1—C11—N2—C12	−179.2 (3)
C3—C2—C7—C6	70.6 (3)	N3—C11—N2—C12	0.4 (4)
C8—C2—C7—C6	−32.9 (3)	C13—C12—N2—C11	26.5 (4)
C4—C5—C8—C9	−62.6 (3)	N2—C11—N3—C14	−0.6 (4)
C6—C5—C8—C9	−172.1 (3)	N1—C11—N3—C14	179.0 (3)
C4—C5—C8—C10	175.3 (3)	C13—C14—N3—C11	−25.8 (4)
C6—C5—C8—C10	65.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.98 (5)	1.90 (5)	2.873 (5)	173 (4)
N1—H2···O2ⁱ	0.77 (5)	2.12 (5)	2.888 (5)	178 (6)
N2—H3···O3	0.78 (4)	2.13 (4)	2.900 (4)	169 (3)
N3—H4···O3ⁱ	0.81 (4)	2.11 (4)	2.908 (4)	165 (3)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₄H₁₀N₃⁺·C₁₀H₁₅O₄S⁻
M_r	331.43
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	7.4207 (4), 7.3115 (4), 16.421 (1)
β (°)	102.899 (1)
V (Å³)	868.46 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.32 × 0.26 × 0.17

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.860, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	5301, 3003, 2630
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.09
No. of reflections	3003
No. of parameters	214
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.30
Absolute structure	Flack (1983), with 1341 Friedel pairs
Absolute structure parameter	0.17 (9)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.98 (5)	1.90 (5)	2.873 (5)	173 (4)
N1—H2···O2ⁱ	0.77 (5)	2.12 (5)	2.888 (5)	178 (6)
N2—H3···O3	0.78 (4)	2.13 (4)	2.900 (4)	169 (3)
N3—H4···O3ⁱ	0.81 (4)	2.11 (4)	2.908 (4)	165 (3)

Symmetry code: (i) x, y+1, z.

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