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The isomorphous structures of 2-methyl-4-nitro­anilinium bromide, C7H9N2O2+·Br-, and 2-methyl-4-nitro­anilinium iodide, C7H9N2O2+·I-, exhibit ionic layers separated by hydro­carbon layers. The hydro­carbon layer stacks head-to-head, while in the ionic layer, the ammonium groups and halide anions inter­act via hydrogen bonds to form infinite chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106011358/gd3015sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106011358/gd3015Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106011358/gd3015IIsup3.hkl
Contains datablock 2ag33_s

CCDC references: 609420; 609421

Comment top

As part of a study of the effect of anions on the crystal structures of anilinium halide salts, the crystal structures of two protonated 2-methyl-4-nitroaniline molecules are reported. The unprotonated case, O2NC7H6NH2, has been studied previously (Ferguson et al., 2001). The authors were investigating the effect that the substituents on the ring had on the packing arrangement and the hydrogen bonding, and they found that the molecules act as double donors and double acceptors of N—H···O hydrogen bonds. The introduction of a halide anion has a significant effect on the packing, as the ammonium groups form N—H···X hydrogen bonds only in the title compounds. We report here the isostructural salts 2-methyl-4-nitroanilinium bromide, (I), and 2-methyl-4-nitroanilinium iodide, (II). The detailed packing of (I) will be discussed, as well as the hydrogen bonding of (II).

The atomic numbering schemes of both compounds are shown in Fig. 1. Fig. 2 shows the one-dimensional arrangement of (I), in which a single layer of cations is embedded between two ionic layers, forming an alternating hydrocarbon–ionic structure. Within the ionic layer, the Br atoms and ammonium groups interact via hydrogen bonds. The cations pack head-to-head in layers parallel to the ab plane. In contrast, the unsubstituted 4-nitroanilinium bromide has a head-to-tail packing arrangement (Lemmerer & Billing, 2006).

Compound (II) has the same packing arrangement as (I) but differs only in the identity of the counterion, I1. The volume of the unit cell is unexpectedly less by 2.2 Å3 for the iodide case, even though the I ion has a larger ionic radius (2.20 Å) than bromide (1.96 Å) (Reference for standard values?). To compensate, the cations pack closer together.

Compound (II) has an extensive network of hydrogen bonding. In the crystal structure, the ions are linked together by N2—H2C···I1···H2B—N2—H2C···I1 hydrogen bonds, forming infinite chains parallel to [001]. At the same time, two adjacent chains are linked in the [100] direction by N2—H2A···I1 hydrogen bonds to form a connected set of infinite chains (Fig. 3). Overall, the hydrogen-bonding scheme is R22(8) (Bernstein et al., 1995). The hydrogen-bonded rings connect I ions and 2-methyl-4-nitroanilinium cations, which are related by a twofold screw axis. The chains form ladders, which are parallel to the ac plane. These ladders are then stacked perpendicular to this plane and are connected to the I ions of adjacent ladders by I1···H2C—N2—H2B···I1 hydrogen bonds, i.e. atoms H2C and H2B have bifurcated hydrogen bonds. These interactions are weaker, as the hydrogen-acceptor distances are 3.245 (1) and 3.238 (1) Å.

Compound (I) has the same hydrogen-bonding sequence in the c direction. However, due to the smaller van der Waals radius of Br, the ladders are connected by a single Br1···H2C—N2 hydrogen bond. The hydrogen-acceptor distance is 3.12 Å. Subsequently, there is only one bifurcated and three simple hydrogen bonds in (I), compared with three simple and two bifurcated hydrogen bonds in (II).

Experimental top

For the preparation of (I), 2-methyl-4-nitroaniline (0.196 g, 1.29 mmol) was added to 48% HBr (18 ml) and the precipitate dissolved by heating the solution. The solution was then cooled to room temperature and yellow crystals of (I) were grown by slow evaporation. Analysis, calculated for C7H9Br1N2O2: C 36.1, H 3.9, N 12.0%; found: C 36.8, H 3.9, N 12.7%.

For the preparation of (II), 2-methyl-4-nitroaniline (0.204 g, 1.34 mmol) was added to 47% HI (1 ml) and the precipitate dissolved with ethanol (10 ml). Yellow crystals of (II) were grown by slow evaporation of the solution mixture. Elemental analysis was not deemed necessary.

Refinement top

H atoms bonded to C and N atoms were refined in idealized positions in the riding-model approximation, with C—H = 0.93 Å and N—H = 0.89 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(N). The NH3 group was allowed to rotate but not to tip. The highest residual peak was 1.92 Å from Br1 in (I) and 1.90 Å from I1 in (II).

Computing details top

For both compounds, data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; 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 DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric units of (a) (I) and (b) (II), showing the atomic numbering schemes. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A packing diagram for (I), viewed along the c axis.
[Figure 3] Fig. 3. The one-dimensional chains of hydrogen bonds (dashed lines) between the ammonium heads and the I anions in (II). Atoms marked with an asterisk (*), hash (#), ampersand (&), `at' sign (@) or double prime ('') are at the symmetry positions (1 − x, 1 − y, 1 − z), (x, y, 1 + z), (1 − x, 1 − y, −z), (x, y, −1 + z) and (1 − x, 1 − y, 2 − z), respectively.
[Figure 4] Fig. 4. The weak hydrogen-bonding interactions (light-grey dashed lines) and strong interactions (black dashed lines) which stabilize the overall structure in (II). Atoms marked with the suffixes a, b, c, d, e and f are at the symmetry positions (1 − x, 1 − y, 1 − z), (1 − x, −1/2 + y, 1/2 − z), (1 − x, −1/2 + y, 3/2 − z), (1 − x, 1/2 + y, 3/2 − z), (x, 3/2 − y, 1/2 + z) and (x, 3/2 − y, −1/2 + z), respectively.
(I) 2-methyl-4-nitroanilinium bromide top
Crystal data top
C7H9N2O2+·BrF(000) = 464
Mr = 233.07Dx = 1.561 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 837 reflections
a = 14.687 (5) Åθ = 3.5–26.0°
b = 9.840 (5) ŵ = 4.11 mm1
c = 6.877 (5) ÅT = 293 K
β = 93.836 (5)°Needle, light yellow
V = 991.6 (9) Å30.24 × 0.08 × 0.04 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1435 reflections with I > 2σ(I)
ϕ and ω scansRint = 0.027
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 25.3°, θmin = 1.4°
Tmin = 0.565, Tmax = 0.850h = 1717
5290 measured reflectionsk = 1110
1798 independent reflectionsl = 78
Refinement top
Refinement on F292 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.058 w = 1/[σ2(Fo2) + (0.1324P)2 + 1.4593P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.220(Δ/σ)max = 0.006
S = 1.21Δρmax = 0.77 e Å3
1798 reflectionsΔρmin = 0.96 e Å3
99 parameters
Crystal data top
C7H9N2O2+·BrV = 991.6 (9) Å3
Mr = 233.07Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.687 (5) ŵ = 4.11 mm1
b = 9.840 (5) ÅT = 293 K
c = 6.877 (5) Å0.24 × 0.08 × 0.04 mm
β = 93.836 (5)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1798 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1435 reflections with I > 2σ(I)
Tmin = 0.565, Tmax = 0.850Rint = 0.027
5290 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05892 restraints
wR(F2) = 0.220H-atom parameters constrained
S = 1.21Δρmax = 0.77 e Å3
1798 reflectionsΔρmin = 0.96 e Å3
99 parameters
Special details top

Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7034 (4)0.4336 (6)0.7821 (11)0.0741 (18)
C20.7922 (4)0.4827 (5)0.8056 (10)0.0802 (19)
C30.8652 (3)0.3925 (7)0.8192 (12)0.085 (2)
H30.92460.42530.83490.102*
C40.8494 (4)0.2534 (7)0.8094 (12)0.091 (2)
C50.7606 (5)0.2043 (5)0.7859 (11)0.088 (2)
H50.75010.11120.77930.105*
C60.6876 (4)0.2945 (7)0.7723 (11)0.082 (2)
H60.62820.26160.75660.098*
C70.8087 (10)0.6328 (13)0.817 (3)0.107 (4)
H7A0.87310.64990.8320.161*
H7B0.77980.66950.92660.161*
H7C0.78370.67520.69950.161*
N10.9253 (9)0.1586 (14)0.824 (2)0.114 (3)
N20.6270 (6)0.5220 (11)0.7677 (12)0.084 (2)
H2A0.57660.47510.78740.126*
H2B0.62190.55920.64950.126*
H2C0.63440.58720.85710.126*
O10.9989 (7)0.1994 (15)0.891 (2)0.163 (4)
O20.9129 (9)0.0386 (14)0.7755 (18)0.157 (4)
Br10.59478 (5)0.60735 (7)0.26192 (10)0.0492 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.074 (3)0.084 (3)0.065 (4)0.004 (3)0.011 (4)0.003 (4)
C20.077 (3)0.088 (3)0.076 (5)0.001 (3)0.009 (4)0.002 (5)
C30.076 (3)0.102 (4)0.078 (5)0.005 (3)0.004 (5)0.001 (5)
C40.092 (3)0.097 (4)0.083 (5)0.015 (3)0.009 (4)0.002 (5)
C50.100 (4)0.083 (4)0.080 (5)0.007 (3)0.005 (5)0.001 (5)
C60.085 (3)0.084 (3)0.075 (5)0.001 (3)0.006 (4)0.001 (4)
C70.095 (7)0.090 (4)0.137 (11)0.008 (4)0.005 (8)0.003 (7)
N10.108 (4)0.119 (5)0.115 (6)0.032 (4)0.006 (5)0.000 (6)
N20.082 (4)0.095 (5)0.075 (5)0.012 (4)0.005 (4)0.007 (5)
O10.095 (5)0.194 (9)0.197 (11)0.027 (6)0.005 (7)0.010 (9)
O20.195 (10)0.121 (6)0.152 (9)0.063 (6)0.006 (8)0.024 (7)
Br10.0581 (6)0.0489 (5)0.0408 (5)0.0089 (3)0.0043 (3)0.0000 (3)
Geometric parameters (Å, º) top
C1—C21.39C5—H50.93
C1—C61.39C6—H60.93
C1—N21.418 (10)C7—H7A0.96
C2—C31.39C7—H7B0.96
C2—C71.498 (14)C7—H7C0.96
C3—C41.39N1—O11.214 (16)
C3—H30.93N1—O21.24 (2)
C4—C51.39N2—H2A0.89
C4—N11.451 (12)N2—H2B0.89
C5—C61.39N2—H2C0.89
C2—C1—C6120C1—C6—H6120
C2—C1—N2121.8 (6)C2—C7—H7A109.5
C6—C1—N2118.2 (6)C2—C7—H7B109.5
C1—C2—C3120H7A—C7—H7B109.5
C1—C2—C7119.7 (7)C2—C7—H7C109.5
C3—C2—C7120.3 (7)H7A—C7—H7C109.5
C4—C3—C2120H7B—C7—H7C109.5
C4—C3—H3120O1—N1—O2121.9 (13)
C2—C3—H3120O1—N1—C4118.3 (13)
C5—C4—C3120O2—N1—C4119.7 (12)
C5—C4—N1119.7 (8)C1—N2—H2A109.5
C3—C4—N1120.3 (8)C1—N2—H2B109.5
C4—C5—C6120H2A—N2—H2B109.5
C4—C5—H5120C1—N2—H2C109.5
C6—C5—H5120H2A—N2—H2C109.5
C5—C6—C1120H2B—N2—H2C109.5
C5—C6—H6120
C6—C1—C2—C30N1—C4—C5—C6179.8 (9)
N2—C1—C2—C3180.0 (7)C4—C5—C6—C10
C6—C1—C2—C7179.7 (10)C2—C1—C6—C50
N2—C1—C2—C70.2 (11)N2—C1—C6—C5180.0 (7)
C1—C2—C3—C40C5—C4—N1—O1162.3 (12)
C7—C2—C3—C4179.7 (10)C3—C4—N1—O117.5 (17)
C2—C3—C4—C50C5—C4—N1—O215.1 (16)
C2—C3—C4—N1179.8 (9)C3—C4—N1—O2165.0 (11)
C3—C4—C5—C60
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Br1i0.892.643.490 (10)159
N2—H2B···Br10.892.713.579 (8)165
N2—H2C···Br1ii0.892.893.563 (9)134
N2—H2C···Br1iii0.893.123.677 (10)122
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x, y+3/2, z+1/2.
(II) 2-methyl-4-nitroanilinium iodide top
Crystal data top
C7H9N2O2+·IF(000) = 536
Mr = 280.06Dx = 1.88 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 576 reflections
a = 14.671 (4) Åθ = 3.5–19.7°
b = 9.830 (3) ŵ = 3.20 mm1
c = 6.875 (2) ÅT = 293 K
β = 93.782 (7)°Needle, yellow
V = 989.4 (5) Å30.14 × 0.06 × 0.03 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1047 reflections with I > 2σ(I)
ϕ and ω scansRint = 0.073
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 25.5°, θmin = 1.4°
Tmin = 0.664, Tmax = 0.911h = 1517
5499 measured reflectionsk = 1111
1846 independent reflectionsl = 88
Refinement top
Refinement on F292 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.070 w = 1/[σ2(Fo2) + (0.1138P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.187(Δ/σ)max = 0.004
S = 0.94Δρmax = 4.27 e Å3
1846 reflectionsΔρmin = 0.85 e Å3
99 parameters
Crystal data top
C7H9N2O2+·IV = 989.4 (5) Å3
Mr = 280.06Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.671 (4) ŵ = 3.20 mm1
b = 9.830 (3) ÅT = 293 K
c = 6.875 (2) Å0.14 × 0.06 × 0.03 mm
β = 93.782 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
1846 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1047 reflections with I > 2σ(I)
Tmin = 0.664, Tmax = 0.911Rint = 0.073
5499 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07092 restraints
wR(F2) = 0.187H-atom parameters constrained
S = 0.94Δρmax = 4.27 e Å3
1846 reflectionsΔρmin = 0.85 e Å3
99 parameters
Special details top

Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996). The application of the twin law suggested by PLATON (Version 170106, Spek, 2003) [1 0 0, 0 − 1 0, 0 0 − 1] made no difference to the r-factor or the residual Q-peaks.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7037 (4)0.4315 (6)0.7801 (11)0.040 (2)
C20.7928 (5)0.4796 (5)0.8032 (12)0.047 (2)
C30.8655 (4)0.3886 (8)0.8163 (12)0.054 (3)
H30.92510.42090.83180.065*
C40.8490 (4)0.2495 (7)0.8062 (12)0.054 (2)
C50.7599 (5)0.2013 (5)0.7830 (11)0.049 (2)
H50.74890.10820.77620.059*
C60.6872 (4)0.2923 (7)0.7699 (11)0.048 (2)
H60.62760.26010.75440.058*
C70.8118 (10)0.6313 (13)0.822 (3)0.078 (5)
H7A0.87580.64770.81070.117*
H7B0.79440.66290.94590.117*
H7C0.77720.6790.71960.117*
N10.9243 (10)0.1569 (15)0.825 (2)0.077 (3)
N20.6273 (6)0.5232 (11)0.7665 (12)0.048 (2)
H2A0.57560.47570.75610.071*
H2B0.63070.57590.66190.071*
H2C0.62830.57480.87290.071*
O10.9969 (8)0.1965 (14)0.896 (2)0.123 (5)
O20.9106 (9)0.0396 (14)0.7834 (18)0.111 (4)
I10.59475 (6)0.60749 (8)0.26188 (11)0.0490 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.042 (4)0.048 (4)0.033 (6)0.001 (3)0.011 (5)0.001 (5)
C20.046 (4)0.048 (4)0.047 (6)0.004 (3)0.007 (5)0.006 (5)
C30.042 (5)0.063 (4)0.058 (7)0.001 (4)0.014 (6)0.001 (6)
C40.059 (4)0.056 (4)0.047 (6)0.010 (4)0.010 (6)0.004 (6)
C50.068 (5)0.044 (5)0.036 (6)0.001 (3)0.011 (6)0.006 (5)
C60.051 (5)0.050 (4)0.044 (6)0.008 (3)0.009 (5)0.002 (5)
C70.061 (9)0.054 (5)0.119 (13)0.009 (5)0.004 (9)0.000 (8)
N10.078 (5)0.083 (6)0.072 (8)0.033 (5)0.019 (6)0.018 (6)
N20.045 (5)0.058 (6)0.040 (6)0.004 (4)0.006 (5)0.011 (5)
O10.066 (6)0.135 (10)0.168 (14)0.029 (6)0.008 (7)0.023 (9)
O20.133 (10)0.084 (6)0.115 (10)0.061 (6)0.003 (8)0.006 (7)
I10.0580 (6)0.0466 (5)0.0425 (5)0.0084 (4)0.0053 (4)0.0000 (4)
Geometric parameters (Å, º) top
C1—C21.39C5—H50.93
C1—C61.39C6—H60.93
C1—N21.436 (10)C7—H7A0.96
C2—C31.39C7—H7B0.96
C2—C71.521 (13)C7—H7C0.96
C3—C41.39N1—O21.202 (19)
C3—H30.93N1—O11.207 (17)
C4—C51.39N2—H2A0.89
C4—N11.431 (13)N2—H2B0.89
C5—C61.39N2—H2C0.89
C2—C1—C6120C1—C6—H6120
C2—C1—N2121.2 (6)C2—C7—H7A109.5
C6—C1—N2118.8 (6)C2—C7—H7B109.5
C1—C2—C3120H7A—C7—H7B109.5
C1—C2—C7120.6 (7)C2—C7—H7C109.5
C3—C2—C7119.4 (7)H7A—C7—H7C109.5
C4—C3—C2120H7B—C7—H7C109.5
C4—C3—H3120O2—N1—O1122.4 (14)
C2—C3—H3120O2—N1—C4118.2 (14)
C3—C4—C5120O1—N1—C4119.1 (14)
C3—C4—N1119.4 (8)C1—N2—H2A109.5
C5—C4—N1120.6 (8)C1—N2—H2B109.5
C4—C5—C6120H2A—N2—H2B109.5
C4—C5—H5120C1—N2—H2C109.5
C6—C5—H5120H2A—N2—H2C109.5
C5—C6—C1120H2B—N2—H2C109.5
C5—C6—H6120
C6—C1—C2—C30N1—C4—C5—C6178.3 (9)
N2—C1—C2—C3179.9 (8)C4—C5—C6—C10
C6—C1—C2—C7177.9 (10)C2—C1—C6—C50
N2—C1—C2—C72.0 (11)N2—C1—C6—C5179.9 (8)
C1—C2—C3—C40C3—C4—N1—O2167.6 (11)
C7—C2—C3—C4177.9 (10)C5—C4—N1—O214.0 (16)
C2—C3—C4—C50C3—C4—N1—O118.3 (17)
C2—C3—C4—N1178.4 (9)C5—C4—N1—O1160.0 (12)
C3—C4—C5—C60
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···I1i0.892.623.495 (10)166
N2—H2C···I1ii0.892.773.568 (9)150
N2—H2B···I10.892.783.568 (8)148
N2—H2B···I1iii0.893.243.662 (10)112
N2—H2C···I1iii0.893.243.662 (10)112
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x, y+3/2, z+1/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC7H9N2O2+·BrC7H9N2O2+·I
Mr233.07280.06
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)293293
a, b, c (Å)14.687 (5), 9.840 (5), 6.877 (5)14.671 (4), 9.830 (3), 6.875 (2)
β (°) 93.836 (5) 93.782 (7)
V3)991.6 (9)989.4 (5)
Z44
Radiation typeMo KαMo Kα
µ (mm1)4.113.20
Crystal size (mm)0.24 × 0.08 × 0.040.14 × 0.06 × 0.03
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Bruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Multi-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.565, 0.8500.664, 0.911
No. of measured, independent and
observed [I > 2σ(I)] reflections
5290, 1798, 1435 5499, 1846, 1047
Rint0.0270.073
(sin θ/λ)max1)0.6000.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.220, 1.21 0.070, 0.187, 0.94
No. of reflections17981846
No. of parameters9999
No. of restraints9292
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.77, 0.964.27, 0.85

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1999), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···Br1i0.892.643.490 (10)159
N2—H2B···Br10.892.713.579 (8)165
N2—H2C···Br1ii0.892.893.563 (9)134
N2—H2C···Br1iii0.893.123.677 (10)122
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x, y+3/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···I1i0.892.623.495 (10)166
N2—H2C···I1ii0.892.773.568 (9)150
N2—H2B···I10.892.783.568 (8)148
N2—H2B···I1iii0.893.243.662 (10)112
N2—H2C···I1iii0.893.243.662 (10)112
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x, y+3/2, z+1/2.
 

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