5-Bromo-3-(methyl­amino­carbon­yl)pyridinium picrate

Sarojini, B.K.; Narayana, B.; Swamy, M.T.; Yathirajan, H.S.; Bolte, M.

doi:10.1107/S1600536807046934

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5-Bromo-3-(methylaminocarbonyl)pyridinium picrate

B. K. Sarojini, B. Narayana, M. T. Swamy, H. S. Yathirajan and M. Bolte

In the title compound, C₇H₈BrN₂O⁺·C₆H₂N₃O₇⁻, the cations and anions are connected by N—H

O hydrogen bonds. Whereas two nitro groups are almost coplanar with the aromatic ring of the picrate anion, the third one is significantly twisted [dihedral angle = 41 (2)°]. The ions crystallize in sheets parallel to the ( $\overline{1}$ $\overline{1}$ 2) plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046934/hb2557sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046934/hb2557Isup2.hkl Contains datablock I

CCDC reference: 663850

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.018 Å
R factor = 0.103
wR factor = 0.263
Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        N11

Author Response: It is not N11 that has a low Ueq, but its the O atoms bonded to N11 that have a rather high Ueq, which might be due to high thermal motion of these two O atoms.


Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         18
PLAT430_ALERT_2_B Short Inter D...A Contact  O16    ..  N12     ..       2.86 Ang.
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1    ..  O1      ..       2.93 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  O11    ..  C6      ..       2.90 Ang.

Alert level C
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.103
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.263
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.122
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT084_ALERT_2_C High R2 Value ..................................       0.26
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT432_ALERT_2_C Short Inter X...Y Contact  O17    ..  C6      ..       2.95 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C6 H2 N3 O7

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           25.59
           From the CIF: _reflns_number_total               2966
           Count of symmetry unique reflns         1558
           Completeness (_total/calc)            190.37%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1408
           Fraction of Friedel pairs measured     0.904
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

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

Comment top

Nicotinamide, also known as niacinamide, is the amide of niacin (vitamin B3) and used for the treatment of arthritis by aiding the body in its production of cartilage. A different use for this compound is an additive in energy drinks (Aranda & Morlock, 2006). The crystal structures of N-(4-bromophenyl)-5,6-dichloronicotinamide and 6-chloro-5-fluoro-N-(3-pyridyl)nicotinamide (Jethmalani et al., 1996), the picrate salt of 1-methylnicotinamide (Freeman & Bugg, 1974) and nicotinium picrate (Anitha et al., 2005) have been reported. In continuation of our work on picrate salts (Yathirajan et al., 2007), the paper reports the crystal structure of the title compound, (I).

Compound (I), [C₇H₈BrN₂O]⁺[C₆H₂N₃O₇]^-, consists of discrete 5-bromo-N-methylnicotinamidium cations and picrate anions connected by N—H···O and bifurcated N—H···(O,O) hydrogen bonds. Whereas two nitro groups are almost coplanar with the aromatic ring of the picrate anion [dihedral angles 4(2)° and 11 (2)°], the third one is significantly twisted [dihedral angle 41 (2)°]. The non-H atoms of the side chain of the cation are almost coplanar (r.m.s. deviation 0.015 Å) and this plane is inclined by 28.9 (8)° with respect to the heterocycle. The ion pairs crystallize in sheets parallel to the (112) plane.

Related literature top

For related structures, see: Anitha et al. (2005); Freeman & Bugg (1974); Jethmalani et al. (1996); Yathirajan et al. (2007). For related literature, see: Kagabu et al. (1998); Aranda & Morlock (2006).

Experimental top

5-Bromo-N-methylnicotinamide (2.15 g, 0.01 mol) was dissolved in 25 ml of 1:1 v/v alcohol-water mixture and few drops of dilute HCl were added and stirred well. To this, picric acid (2.29 g, 0.01 mol) in 30 ml of water was added dropwise and stirred for few minutes. The precipitated salt was filtered, dried and yellow blocks of (I) were obtained by slow evaporation of the ethanol solution. (m. p.: 401–403 K). Analysis for C₁₃H₁₀BrN₅O₈: Found (Calculated): C 35.04 (35.15); H 2.24 (2.27); N 15.71% (15.77%).

Structure description top

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Perspective view of (I) displacement ellipsoids for the non-hydrogen atoms are at the 50% probability level. Hydrogen bonds shown as dashed lines.
	Fig. 2. Packing diagram of the title compound. Hydrogen bonds shown as dashed lines.

5-Bromo-3-(methylaminocarbonyl)pyridinium picrate top

Crystal data top

C₇H₈BrN₂O⁺·C₆H₂N₃O₇⁻	Z = 1
M_r = 444.17	F(000) = 222
Triclinic, P1	D_x = 1.791 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6684 (7) Å	Cell parameters from 5412 reflections
b = 7.0328 (11) Å	θ = 3.5–25.7°
c = 12.842 (2) Å	µ = 2.55 mm⁻¹
α = 93.802 (13)°	T = 173 K
β = 97.688 (13)°	Block, yellow
γ = 98.280 (12)°	0.22 × 0.20 × 0.19 mm
V = 411.90 (11) Å³

Data collection top

Stoe IPDSII two-circle diffractometer	2966 independent reflections
Radiation source: fine-focus sealed tube	2898 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.122
ω scans	θ_max = 25.6°, θ_min = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −5→5
T_min = 0.604, T_max = 0.643	k = −8→8
6268 measured reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.103	H-atom parameters constrained
wR(F²) = 0.263	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
2966 reflections	Δρ_max = 1.15 e Å⁻³
244 parameters	Δρ_min = −1.30 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1416 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (3)

Crystal data top

C₇H₈BrN₂O⁺·C₆H₂N₃O₇⁻	γ = 98.280 (12)°
M_r = 444.17	V = 411.90 (11) Å³
Triclinic, P1	Z = 1
a = 4.6684 (7) Å	Mo Kα radiation
b = 7.0328 (11) Å	µ = 2.55 mm⁻¹
c = 12.842 (2) Å	T = 173 K
α = 93.802 (13)°	0.22 × 0.20 × 0.19 mm
β = 97.688 (13)°

Data collection top

Stoe IPDSII two-circle diffractometer	2966 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	2898 reflections with I > 2σ(I)
T_min = 0.604, T_max = 0.643	R_int = 0.122
6268 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.103	H-atom parameters constrained
wR(F²) = 0.263	Δρ_max = 1.15 e Å⁻³
S = 1.15	Δρ_min = −1.30 e Å⁻³
2966 reflections	Absolute structure: Flack (1983), 1416 Friedel pairs
244 parameters	Absolute structure parameter: 0.06 (3)
3 restraints

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
Br1	0.80717 (7)	0.12358 (7)	0.79387 (6)	0.0446 (4)
O1	0.0789 (16)	0.8106 (13)	0.8851 (7)	0.0452 (18)
N1	0.547 (2)	0.8204 (15)	0.9724 (8)	0.040 (2)
H1	0.7077	0.7676	0.9783	0.048*
C1	0.379 (2)	0.5947 (18)	0.8161 (10)	0.041 (2)
C2	0.560 (3)	0.4597 (17)	0.8415 (10)	0.042 (2)
H2	0.6673	0.4644	0.9102	0.050*
C3	0.582 (3)	0.313 (2)	0.7614 (10)	0.050 (3)
C4	0.419 (2)	0.3107 (16)	0.6629 (9)	0.041 (2)
H4	0.4312	0.2147	0.6088	0.050*
N5	0.240 (3)	0.4456 (15)	0.6434 (8)	0.039 (2)
H5	0.1387	0.4418	0.5801	0.047*
C6	0.212 (3)	0.584 (2)	0.7170 (10)	0.040 (2)
H6	0.0800	0.6728	0.7018	0.048*
C7	0.323 (2)	0.7498 (19)	0.8939 (11)	0.038 (2)
C8	0.526 (3)	0.979 (2)	1.0457 (11)	0.056 (3)
H8A	0.3871	1.0576	1.0129	0.085*
H8B	0.7186	1.0586	1.0651	0.085*
H8C	0.4573	0.9299	1.1091	0.085*
C11	−0.484 (3)	0.7005 (19)	0.3974 (11)	0.047 (3)
C12	−0.299 (3)	0.5557 (19)	0.4251 (11)	0.046 (2)
C13	−0.292 (2)	0.4168 (19)	0.3371 (9)	0.045 (2)
C14	−0.469 (2)	0.4101 (18)	0.2417 (8)	0.042 (2)
H14	−0.4666	0.3117	0.1876	0.051*
C15	−0.649 (3)	0.5457 (19)	0.2252 (10)	0.046 (2)
C16	−0.654 (3)	0.6999 (18)	0.3012 (9)	0.042 (2)
H16	−0.7683	0.7986	0.2864	0.051*
N11	−0.491 (3)	0.8562 (17)	0.4781 (10)	0.049 (2)
N12	−0.103 (3)	0.2703 (18)	0.3510 (8)	0.051 (2)
N13	−0.839 (3)	0.5355 (19)	0.1231 (10)	0.055 (3)
O11	−0.172 (3)	0.553 (2)	0.5176 (8)	0.072 (3)
O12	0.081 (2)	0.2845 (16)	0.4273 (8)	0.060 (2)
O13	−0.115 (2)	0.143 (2)	0.2774 (9)	0.068 (3)
O14	−0.828 (3)	0.416 (2)	0.0549 (10)	0.073 (4)
O15	−1.009 (2)	0.660 (2)	0.1133 (10)	0.068 (3)
O16	−0.498 (6)	1.018 (3)	0.4500 (17)	0.124 (7)
O17	−0.488 (8)	0.822 (3)	0.5712 (18)	0.162 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0394 (5)	0.0423 (5)	0.0511 (6)	0.0075 (3)	0.0010 (3)	0.0043 (3)
O1	0.030 (4)	0.049 (4)	0.054 (5)	0.008 (3)	−0.002 (3)	0.002 (4)
N1	0.031 (5)	0.049 (5)	0.038 (5)	0.008 (4)	−0.002 (4)	−0.006 (4)
C1	0.030 (5)	0.045 (6)	0.038 (6)	−0.008 (4)	−0.013 (4)	0.007 (5)
C2	0.040 (5)	0.043 (5)	0.038 (5)	−0.004 (4)	−0.001 (4)	0.006 (4)
C3	0.041 (6)	0.062 (7)	0.041 (6)	−0.011 (5)	−0.001 (5)	0.013 (5)
C4	0.039 (5)	0.041 (5)	0.040 (5)	0.004 (4)	0.001 (4)	−0.008 (4)
N5	0.041 (5)	0.038 (5)	0.034 (5)	0.007 (4)	−0.008 (4)	0.004 (4)
C6	0.040 (6)	0.051 (7)	0.031 (6)	0.015 (5)	−0.002 (5)	0.010 (5)
C7	0.025 (5)	0.041 (6)	0.044 (6)	0.000 (4)	−0.004 (5)	0.007 (5)
C8	0.050 (6)	0.066 (8)	0.049 (7)	0.006 (6)	0.004 (5)	−0.019 (6)
C11	0.045 (6)	0.052 (6)	0.044 (7)	0.011 (5)	−0.002 (5)	0.008 (5)
C12	0.047 (6)	0.051 (6)	0.036 (6)	0.006 (5)	−0.002 (5)	0.002 (5)
C13	0.036 (5)	0.057 (6)	0.038 (5)	0.000 (4)	−0.001 (4)	0.006 (5)
C14	0.040 (5)	0.056 (6)	0.026 (4)	−0.004 (5)	0.002 (4)	0.001 (4)
C15	0.048 (6)	0.048 (6)	0.034 (6)	−0.006 (5)	−0.003 (5)	0.002 (4)
C16	0.049 (6)	0.045 (5)	0.030 (5)	0.004 (4)	−0.003 (5)	0.008 (4)
N11	0.053 (6)	0.044 (6)	0.041 (6)	−0.005 (4)	−0.006 (4)	0.003 (5)
N12	0.053 (6)	0.064 (7)	0.032 (4)	0.008 (5)	0.001 (4)	−0.010 (4)
N13	0.051 (6)	0.066 (8)	0.038 (6)	−0.008 (5)	−0.016 (5)	0.006 (5)
O11	0.075 (7)	0.098 (9)	0.038 (5)	0.026 (6)	−0.019 (5)	−0.007 (5)
O12	0.063 (6)	0.065 (6)	0.050 (5)	0.020 (5)	−0.003 (4)	0.001 (4)
O13	0.063 (7)	0.079 (7)	0.058 (6)	0.028 (6)	−0.011 (5)	−0.015 (5)
O14	0.090 (9)	0.079 (8)	0.037 (6)	−0.016 (6)	0.000 (6)	−0.008 (6)
O15	0.047 (5)	0.098 (9)	0.055 (6)	0.009 (5)	−0.013 (5)	0.030 (6)
O16	0.20 (2)	0.078 (10)	0.115 (13)	0.060 (12)	0.048 (14)	0.026 (9)
O17	0.30 (4)	0.081 (12)	0.080 (13)	−0.013 (17)	0.014 (18)	−0.032 (11)

Geometric parameters (Å, º) top

Br1—C3	1.848 (15)	C11—C16	1.373 (17)
O1—C7	1.268 (15)	C11—C12	1.461 (18)
N1—C7	1.363 (15)	C11—N11	1.464 (19)
N1—C8	1.436 (16)	C12—O11	1.257 (17)
N1—H1	0.8800	C12—C13	1.451 (18)
C1—C2	1.386 (18)	C13—C14	1.377 (15)
C1—C6	1.393 (17)	C13—N12	1.455 (18)
C1—C7	1.51 (2)	C14—C15	1.367 (19)
C2—C3	1.430 (19)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.414 (19)
C3—C4	1.385 (16)	C15—N13	1.472 (15)
C4—N5	1.367 (16)	C16—H16	0.9500
C4—H4	0.9500	N11—O16	1.22 (2)
N5—C6	1.343 (18)	N11—O17	1.23 (3)
N5—H5	0.8800	N12—O12	1.202 (15)
C6—H6	0.9500	N12—O13	1.246 (16)
C8—H8A	0.9800	N13—O14	1.18 (2)
C8—H8B	0.9800	N13—O15	1.265 (19)
C8—H8C	0.9800

C7—N1—C8	121.2 (11)	H8B—C8—H8C	109.5
C7—N1—H1	119.4	C16—C11—C12	124.6 (12)
C8—N1—H1	119.4	C16—C11—N11	117.9 (11)
C2—C1—C6	121.3 (14)	C12—C11—N11	117.5 (11)
C2—C1—C7	123.9 (10)	O11—C12—C13	125.6 (13)
C6—C1—C7	114.6 (11)	O11—C12—C11	121.6 (13)
C1—C2—C3	118.2 (11)	C13—C12—C11	112.8 (11)
C1—C2—H2	120.9	C14—C13—C12	123.0 (12)
C3—C2—H2	120.9	C14—C13—N12	117.8 (11)
C4—C3—C2	118.8 (12)	C12—C13—N12	119.1 (10)
C4—C3—Br1	121.6 (10)	C15—C14—C13	119.6 (11)
C2—C3—Br1	119.6 (9)	C15—C14—H14	120.2
N5—C4—C3	120.2 (11)	C13—C14—H14	120.2
N5—C4—H4	119.9	C14—C15—C16	122.6 (11)
C3—C4—H4	119.9	C14—C15—N13	118.9 (12)
C6—N5—C4	122.6 (10)	C16—C15—N13	118.4 (12)
C6—N5—H5	118.7	C11—C16—C15	117.0 (12)
C4—N5—H5	118.7	C11—C16—H16	121.5
N5—C6—C1	118.8 (12)	C15—C16—H16	121.5
N5—C6—H6	120.6	O16—N11—O17	122.2 (19)
C1—C6—H6	120.6	O16—N11—C11	117.8 (14)
O1—C7—N1	122.7 (13)	O17—N11—C11	120.0 (16)
O1—C7—C1	120.7 (11)	O12—N12—O13	120.9 (12)
N1—C7—C1	116.6 (10)	O12—N12—C13	120.0 (11)
N1—C8—H8A	109.5	O13—N12—C13	118.6 (10)
N1—C8—H8B	109.5	O14—N13—O15	122.9 (13)
H8A—C8—H8B	109.5	O14—N13—C15	120.6 (14)
N1—C8—H8C	109.5	O15—N13—C15	116.5 (13)
H8A—C8—H8C	109.5

C6—C1—C2—C3	3.0 (16)	O11—C12—C13—N12	−7 (2)
C7—C1—C2—C3	176.6 (9)	C11—C12—C13—N12	176.4 (11)
C1—C2—C3—C4	−1.0 (16)	C12—C13—C14—C15	3.9 (18)
C1—C2—C3—Br1	−177.0 (8)	N12—C13—C14—C15	−179.6 (11)
C2—C3—C4—N5	−0.2 (17)	C13—C14—C15—C16	2.7 (19)
Br1—C3—C4—N5	175.7 (9)	C13—C14—C15—N13	−179.5 (11)
C3—C4—N5—C6	−0.4 (18)	C12—C11—C16—C15	1 (2)
C4—N5—C6—C1	2.3 (18)	N11—C11—C16—C15	−178.5 (12)
C2—C1—C6—N5	−3.6 (17)	C14—C15—C16—C11	−5 (2)
C7—C1—C6—N5	−177.8 (11)	N13—C15—C16—C11	177.1 (11)
C8—N1—C7—O1	−4.7 (19)	C16—C11—N11—O16	−39 (2)
C8—N1—C7—C1	174.8 (12)	C12—C11—N11—O16	140.9 (19)
C2—C1—C7—O1	−148.3 (11)	C16—C11—N11—O17	141 (2)
C6—C1—C7—O1	25.6 (15)	C12—C11—N11—O17	−39 (3)
C2—C1—C7—N1	32.1 (16)	C14—C13—N12—O12	170.6 (12)
C6—C1—C7—N1	−153.9 (11)	C12—C13—N12—O12	−12.7 (18)
C16—C11—C12—O11	−172.7 (15)	C14—C13—N12—O13	−1.7 (18)
N11—C11—C12—O11	7 (2)	C12—C13—N12—O13	174.9 (12)
C16—C11—C12—C13	5 (2)	C14—C15—N13—O14	−3 (2)
N11—C11—C12—C13	−175.8 (11)	C16—C15—N13—O14	175.1 (14)
O11—C12—C13—C14	170.0 (14)	C14—C15—N13—O15	177.3 (12)
C11—C12—C13—C14	−7.1 (18)	C16—C15—N13—O15	−4.9 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.23	2.865 (13)	129
N1—H1···O15ⁱⁱ	0.88	2.28	2.964 (14)	135
N5—H5···O11	0.88	1.86	2.572 (15)	137
N5—H5···O12	0.88	2.15	2.885 (15)	140

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

Experimental details

Crystal data
Chemical formula	C₇H₈BrN₂O⁺·C₆H₂N₃O₇⁻
M_r	444.17
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	4.6684 (7), 7.0328 (11), 12.842 (2)
α, β, γ (°)	93.802 (13), 97.688 (13), 98.280 (12)
V (Å³)	411.90 (11)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.55
Crystal size (mm)	0.22 × 0.20 × 0.19

Data collection
Diffractometer	Stoe IPDSII two-circle
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.604, 0.643
No. of measured, independent and observed [I > 2σ(I)] reflections	6268, 2966, 2898
R_int	0.122
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.103, 0.263, 1.15
No. of reflections	2966
No. of parameters	244
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.15, −1.30
Absolute structure	Flack (1983), 1416 Friedel pairs
Absolute structure parameter	0.06 (3)

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.23	2.865 (13)	129
N1—H1···O15ⁱⁱ	0.88	2.28	2.964 (14)	135
N5—H5···O11	0.88	1.86	2.572 (15)	137
N5—H5···O12	0.88	2.15	2.885 (15)	140

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

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