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In the title compound {systematic name: 10,11-dihydro-5H- dibenz[b,f]azepine-5-carboxamide-formamide solvate (1/1)}, C15H14N2O·CH3NO, the dihydro­carbamazepine and form­amide mol­ecules are hydrogen bonded to form an R22(8) dimer, which is further connected to form a ladder motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041049/wn2194sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041049/wn2194Isup2.hkl
Contains datablock I

CCDC reference: 660350

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.074
  • wR factor = 0.193
  • Data-to-parameter ratio = 63.7

checkCIF/PLATON results

No syntax errors found



Alert level A REFLT03_ALERT_3_A Reflection count > 15% excess reflns - sys abs data present? From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _diffrn_reflns_theta_full 26.00 From the CIF: _reflns_number_total 13441 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2824 Completeness (_total/calc) 475.96%
Author Response: Twinned crystal. Data treated using the HKLF 5 convention. The number given for reflection count thus refers to all reflections from BOTH twin components.
PLAT021_ALERT_1_A Ratio Unique / Expected Reflections too High ...       4.76
Author Response: See above response.

Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.624 1.000 Tmin(prime) and Tmax expected: 0.993 0.998 RR(prime) = 0.628 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.63
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.106 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 40 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.998 Tmax scaled 0.998 Tmin scaled 0.623
2 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 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 6 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

10,11-Dihydrocarbamazepine (DHC) is a recognized impurity in carbamazepine (CBZ), a dibenzazepine drug used to control seizures (Cyr et al., 1987). DHC is known to crystallize in three polymorphic forms: monoclinic form I (Bandoli et al., 1992), orthorhombic form II (Harrison et al., 2006) and triclinic form III (Leech et al., 2007). The title compound was produced during an automated parallel crystallization study (Florence, Johnston, Fernandes et al., 2006) on DHC as part of a wider study into the predicted and experimental structures of CBZ (Florence, Johnston, Price et al., 2006; Florence, Leech et al., 2006) and related molecules (Leech et al., 2007). The sample was identified as a new form using multi-sample foil transmission X-ray powder diffraction analysis (Florence et al., 2003). Subsequent manual recrystallization, from a saturated formamide solution by slow evaporation at 298 K, yielded single crystals suitable for X-ray diffraction (Fig. 1).

The molecules adopt a hydrogen-bonded arrangement similar to that observed in the DHC acetic acid (1/1) (Johnston et al., 2006) and DHC formic acid (1/1) solvates (Johnston et al., 2007). Specifically, the DHC and formamide molecules are connected via N2—H2N···O2 and N3—H4N···O1 hydrogen bonds to form an R22(8) (Etter, 1990) dimer motif (Table 1). Two further hydrogen bonds, N2—H1···O2i and N3—H3N···O1ii form centrosymmetric R24(8) motifs that link the R22(8) DHC/formamide dimers in a ladder arrangement running parallel to the c axis (Fig. 2).

Related literature top

For details of experimental methods used to obtain this compound, see: Florence et al. (2003); Florence, Johnston, Fernandes et al. (2006). For related crystal structures, see: Bandoli et al. (1992); Cyr et al. (1987); Harrison et al. (2006); Leech et al. (2007); Fleischman et al. (2003); Florence, Johnston, Price et al. (2006); Florence, Leech et al. (2006); Johnston et al. (2006, 2007). For related literature, see: Etter (1990).

Experimental top

DHC was used as received from SigmaAldrich and a single-crystal sample of the title compound was obtained by isothermal solvent evaporation of a saturated formamide solution at 298 K.

Refinement top

All crystals examined were twinned by a 180° rotation about -1 1 0. The model reported utilized the SHELX HKLF 5 convention where the ratio of the two twin components refined to 0.518 (3):0.482 (3). H atoms in the formamide solvent and the NH2 group of the DHC molecule were found by difference synthesis and refined isotropically; C—H = 1.026 (19) and N—H = 0.87 (2)–0.94 (2) Å. All other H atoms were constrained to idealized geometry with riding models: Uiso(H) = 1.2Ueq(C); C—H distances = 0.95 and 0.99 Å for CH and CH2 groups, respectively.

Structure description top

10,11-Dihydrocarbamazepine (DHC) is a recognized impurity in carbamazepine (CBZ), a dibenzazepine drug used to control seizures (Cyr et al., 1987). DHC is known to crystallize in three polymorphic forms: monoclinic form I (Bandoli et al., 1992), orthorhombic form II (Harrison et al., 2006) and triclinic form III (Leech et al., 2007). The title compound was produced during an automated parallel crystallization study (Florence, Johnston, Fernandes et al., 2006) on DHC as part of a wider study into the predicted and experimental structures of CBZ (Florence, Johnston, Price et al., 2006; Florence, Leech et al., 2006) and related molecules (Leech et al., 2007). The sample was identified as a new form using multi-sample foil transmission X-ray powder diffraction analysis (Florence et al., 2003). Subsequent manual recrystallization, from a saturated formamide solution by slow evaporation at 298 K, yielded single crystals suitable for X-ray diffraction (Fig. 1).

The molecules adopt a hydrogen-bonded arrangement similar to that observed in the DHC acetic acid (1/1) (Johnston et al., 2006) and DHC formic acid (1/1) solvates (Johnston et al., 2007). Specifically, the DHC and formamide molecules are connected via N2—H2N···O2 and N3—H4N···O1 hydrogen bonds to form an R22(8) (Etter, 1990) dimer motif (Table 1). Two further hydrogen bonds, N2—H1···O2i and N3—H3N···O1ii form centrosymmetric R24(8) motifs that link the R22(8) DHC/formamide dimers in a ladder arrangement running parallel to the c axis (Fig. 2).

For details of experimental methods used to obtain this compound, see: Florence et al. (2003); Florence, Johnston, Fernandes et al. (2006). For related crystal structures, see: Bandoli et al. (1992); Cyr et al. (1987); Harrison et al. (2006); Leech et al. (2007); Fleischman et al. (2003); Florence, Johnston, Price et al. (2006); Florence, Leech et al. (2006); Johnston et al. (2006, 2007). For related literature, see: Etter (1990).

Computing details top

Data collection: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Plot showing the hydrogen-bonded dimer arrangement in the title compound, with three R22(8) dimers linked in a ladder arrangement via two R42(8) motifs. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (b) -x + 1, -y, -z + 2, (c) -x + 1, -y, -z + 1.]
10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide–formamide solvate (1/1) top
Crystal data top
C15H14N2O·CH3NOZ = 2
Mr = 283.33F(000) = 300
Triclinic, P1Dx = 1.313 Mg m3
a = 8.4690 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.0215 (4) ÅCell parameters from 3115 reflections
c = 10.3137 (4) Åθ = 2.9–27.5°
α = 74.363 (3)°µ = 0.09 mm1
β = 83.630 (3)°T = 120 K
γ = 70.847 (3)°Slab, colourless
V = 716.61 (5) Å30.08 × 0.06 × 0.02 mm
Data collection top
Bruker Nonius 95mm CCD camera on κ-goniostat
diffractometer
13441 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode7956 reflections with I > 2σ(I)
10cm confocal mirrors monochromatorRint = 0.106
Detector resolution: 9.091 pixels mm-1θmax = 26.0°, θmin = 2.9°
φ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
k = 1111
Tmin = 0.624, Tmax = 1l = 1212
16142 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.074 w = 1/[σ2(Fo2) + (0.0295P)2 + 2.9523P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.194(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.37 e Å3
13441 reflectionsΔρmin = 0.34 e Å3
211 parameters
Crystal data top
C15H14N2O·CH3NOγ = 70.847 (3)°
Mr = 283.33V = 716.61 (5) Å3
Triclinic, P1Z = 2
a = 8.4690 (4) ÅMo Kα radiation
b = 9.0215 (4) ŵ = 0.09 mm1
c = 10.3137 (4) ÅT = 120 K
α = 74.363 (3)°0.08 × 0.06 × 0.02 mm
β = 83.630 (3)°
Data collection top
Bruker Nonius 95mm CCD camera on κ-goniostat
diffractometer
13441 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
7956 reflections with I > 2σ(I)
Tmin = 0.624, Tmax = 1Rint = 0.106
16142 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0740 restraints
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.37 e Å3
13441 reflectionsΔρmin = 0.34 e Å3
211 parameters
Special details top

Experimental. Data collection at Soton service 2006src1503. Data treated as twinned (180 ° rot) about -1 1 0 hklf 5 file created. SADABS does not output Tmin and Tmax - but the ratio is reported as 0.62441.

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
xyzUiso*/Ueq
O10.66395 (16)0.07647 (16)0.62574 (12)0.0278 (3)
N10.78725 (19)0.21960 (19)0.70960 (15)0.0228 (4)
N20.6485 (2)0.0536 (2)0.85028 (17)0.0318 (4)
C10.8002 (2)0.2875 (2)0.81820 (18)0.0237 (5)
C20.9315 (2)0.2155 (2)0.90536 (18)0.0269 (5)
H21.01450.11780.89630.032*
C30.9412 (3)0.2868 (3)1.00620 (19)0.0305 (5)
H31.02990.23751.06800.037*
C40.8201 (3)0.4309 (3)1.01629 (19)0.0339 (5)
H40.82630.48011.08540.041*
C50.6905 (3)0.5036 (3)0.92678 (19)0.0303 (5)
H50.60950.60310.93390.036*
C60.6782 (2)0.4316 (2)0.82621 (19)0.0268 (5)
C70.5462 (2)0.5087 (2)0.72184 (18)0.0279 (5)
H7A0.45670.59680.75100.034*
H7B0.49590.42700.71340.034*
C80.6176 (2)0.5775 (2)0.58525 (19)0.0287 (5)
H8A0.52500.62640.52100.034*
H8B0.65660.66630.59410.034*
C90.7598 (2)0.4634 (2)0.52278 (19)0.0247 (5)
C100.8252 (2)0.5318 (3)0.39736 (19)0.0273 (5)
H100.77840.64430.35790.033*
C110.9537 (3)0.4415 (3)0.33078 (19)0.0293 (5)
H110.99530.49170.24690.035*
C121.0230 (3)0.2771 (3)0.38566 (19)0.0294 (5)
H121.10980.21300.33860.035*
C130.9645 (2)0.2072 (2)0.50968 (19)0.0249 (5)
H131.01390.09500.54910.030*
C140.8346 (2)0.2986 (2)0.57749 (18)0.0223 (4)
C150.6970 (2)0.1151 (2)0.72422 (18)0.0244 (5)
O20.36473 (18)0.07760 (18)0.86899 (13)0.0367 (4)
N30.3791 (2)0.0440 (2)0.64367 (17)0.0297 (4)
C160.3135 (3)0.0850 (3)0.7648 (2)0.0286 (5)
H1N0.659 (3)0.095 (2)0.921 (2)0.037 (6)*
H2N0.575 (3)0.004 (2)0.859 (2)0.032 (6)*
H3N0.347 (3)0.065 (2)0.573 (2)0.036 (6)*
H4N0.475 (3)0.010 (3)0.631 (2)0.043 (7)*
H160.214 (2)0.127 (2)0.7653 (18)0.028 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0350 (8)0.0344 (9)0.0213 (7)0.0180 (7)0.0003 (6)0.0100 (6)
N10.0284 (9)0.0260 (10)0.0166 (8)0.0136 (8)0.0009 (7)0.0039 (7)
N20.0453 (12)0.0383 (12)0.0207 (10)0.0262 (10)0.0015 (9)0.0065 (9)
C10.0292 (11)0.0288 (12)0.0173 (10)0.0165 (10)0.0022 (9)0.0043 (9)
C20.0290 (11)0.0297 (12)0.0235 (11)0.0142 (10)0.0022 (9)0.0023 (9)
C30.0292 (12)0.0422 (14)0.0228 (11)0.0193 (11)0.0046 (9)0.0009 (10)
C40.0455 (14)0.0485 (15)0.0197 (11)0.0292 (12)0.0012 (10)0.0106 (10)
C50.0314 (12)0.0349 (13)0.0270 (12)0.0131 (10)0.0051 (9)0.0106 (10)
C60.0289 (12)0.0341 (13)0.0217 (11)0.0166 (10)0.0014 (9)0.0064 (9)
C70.0272 (11)0.0329 (12)0.0247 (11)0.0095 (9)0.0027 (9)0.0079 (9)
C80.0259 (11)0.0300 (12)0.0296 (12)0.0072 (10)0.0027 (9)0.0075 (9)
C90.0240 (11)0.0312 (12)0.0236 (11)0.0130 (9)0.0074 (9)0.0066 (9)
C100.0291 (12)0.0299 (12)0.0242 (11)0.0128 (10)0.0076 (9)0.0014 (9)
C110.0337 (12)0.0433 (14)0.0179 (10)0.0239 (11)0.0006 (9)0.0041 (10)
C120.0312 (12)0.0369 (14)0.0259 (12)0.0131 (10)0.0015 (9)0.0150 (10)
C130.0279 (11)0.0252 (11)0.0241 (11)0.0103 (9)0.0035 (9)0.0068 (9)
C140.0248 (11)0.0277 (12)0.0196 (10)0.0150 (9)0.0023 (8)0.0052 (9)
C150.0285 (11)0.0251 (12)0.0204 (11)0.0105 (9)0.0021 (9)0.0037 (9)
O20.0442 (9)0.0517 (10)0.0228 (8)0.0262 (8)0.0016 (7)0.0103 (7)
N30.0329 (11)0.0411 (12)0.0199 (10)0.0177 (9)0.0018 (8)0.0088 (8)
C160.0294 (12)0.0319 (13)0.0272 (12)0.0128 (10)0.0004 (10)0.0079 (10)
Geometric parameters (Å, º) top
O1—C151.245 (2)C7—H7B0.9900
N1—C151.366 (2)C8—C91.515 (3)
N1—C141.438 (2)C8—H8A0.9900
N1—C11.444 (2)C8—H8B0.9900
N2—C151.345 (2)C9—C141.393 (3)
N2—H1N0.93 (2)C9—C101.413 (3)
N2—H2N0.87 (2)C10—C111.369 (3)
C1—C21.378 (3)C10—H100.9500
C1—C61.386 (3)C11—C121.384 (3)
C2—C31.384 (3)C11—H110.9500
C2—H20.9500C12—C131.382 (3)
C3—C41.389 (3)C12—H120.9500
C3—H30.9500C13—C141.387 (3)
C4—C51.383 (3)C13—H130.9500
C4—H40.9500O2—C161.228 (2)
C5—C61.393 (3)N3—C161.318 (3)
C5—H50.9500N3—H3N0.88 (2)
C6—C71.499 (3)N3—H4N0.94 (2)
C7—C81.524 (3)C16—H161.026 (19)
C7—H7A0.9900
C15—N1—C14120.22 (14)C7—C8—H8A107.8
C15—N1—C1121.60 (15)C9—C8—H8B107.8
C14—N1—C1116.19 (14)C7—C8—H8B107.8
C15—N2—H1N120.6 (13)H8A—C8—H8B107.1
C15—N2—H2N117.3 (13)C14—C9—C10116.65 (19)
H1N—N2—H2N117.9 (19)C14—C9—C8126.67 (17)
C2—C1—C6122.17 (18)C10—C9—C8116.67 (19)
C2—C1—N1121.25 (18)C11—C10—C9122.3 (2)
C6—C1—N1116.52 (17)C11—C10—H10118.9
C1—C2—C3119.3 (2)C9—C10—H10118.9
C1—C2—H2120.3C10—C11—C12119.96 (18)
C3—C2—H2120.3C10—C11—H11120.0
C2—C3—C4119.43 (19)C12—C11—H11120.0
C2—C3—H3120.3C13—C12—C11119.20 (19)
C4—C3—H3120.3C13—C12—H12120.4
C5—C4—C3120.70 (19)C11—C12—H12120.4
C5—C4—H4119.6C12—C13—C14120.90 (19)
C3—C4—H4119.6C12—C13—H13119.5
C4—C5—C6120.3 (2)C14—C13—H13119.5
C4—C5—H5119.8C13—C14—C9120.99 (17)
C6—C5—H5119.8C13—C14—N1117.68 (18)
C1—C6—C5118.01 (18)C9—C14—N1121.21 (17)
C1—C6—C7119.05 (17)O1—C15—N2121.61 (18)
C5—C6—C7122.8 (2)O1—C15—N1121.52 (17)
C6—C7—C8111.57 (16)N2—C15—N1116.85 (16)
C6—C7—H7A109.3C16—N3—H3N121.0 (13)
C8—C7—H7A109.3C16—N3—H4N121.2 (13)
C6—C7—H7B109.3H3N—N3—H4N116.8 (19)
C8—C7—H7B109.3O2—C16—N3124.7 (2)
H7A—C7—H7B108.0O2—C16—H16121.8 (10)
C9—C8—C7118.16 (17)N3—C16—H16113.5 (10)
C9—C8—H8A107.8
C15—N1—C1—C293.5 (2)C14—C9—C10—C111.1 (3)
C14—N1—C1—C2102.6 (2)C8—C9—C10—C11179.94 (17)
C15—N1—C1—C689.2 (2)C9—C10—C11—C120.5 (3)
C14—N1—C1—C674.8 (2)C10—C11—C12—C132.0 (3)
C6—C1—C2—C31.3 (3)C11—C12—C13—C141.9 (3)
N1—C1—C2—C3178.50 (16)C12—C13—C14—C90.2 (3)
C1—C2—C3—C41.1 (3)C12—C13—C14—N1176.34 (16)
C2—C3—C4—C50.0 (3)C10—C9—C14—C131.3 (2)
C3—C4—C5—C61.0 (3)C8—C9—C14—C13179.96 (18)
C2—C1—C6—C50.3 (3)C10—C9—C14—N1174.74 (15)
N1—C1—C6—C5177.66 (16)C8—C9—C14—N14.0 (3)
C2—C1—C6—C7175.70 (17)C15—N1—C14—C1375.5 (2)
N1—C1—C6—C71.6 (3)C1—N1—C14—C13120.26 (19)
C4—C5—C6—C10.8 (3)C15—N1—C14—C9108.3 (2)
C4—C5—C6—C7176.68 (18)C1—N1—C14—C955.9 (2)
C1—C6—C7—C870.4 (2)C14—N1—C15—O15.3 (3)
C5—C6—C7—C8105.5 (2)C1—N1—C15—O1168.59 (18)
C6—C7—C8—C957.7 (2)C14—N1—C15—N2176.03 (18)
C7—C8—C9—C140.1 (3)C1—N1—C15—N212.7 (3)
C7—C8—C9—C10178.80 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O20.87 (2)2.12 (2)2.975 (2)170.0 (19)
N2—H1N···O2i0.93 (2)2.12 (2)2.948 (2)147.6 (17)
N3—H4N···O10.94 (2)1.99 (2)2.924 (2)172.2 (19)
N3—H3N···O1ii0.88 (2)2.10 (2)2.945 (2)159.7 (18)
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC15H14N2O·CH3NO
Mr283.33
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)8.4690 (4), 9.0215 (4), 10.3137 (4)
α, β, γ (°)74.363 (3), 83.630 (3), 70.847 (3)
V3)716.61 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.08 × 0.06 × 0.02
Data collection
DiffractometerBruker Nonius 95mm CCD camera on κ-goniostat
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.624, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
16142, 13441, 7956
Rint0.106
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.194, 1.04
No. of reflections13441
No. of parameters211
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.34

Computer programs: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997), COLLECT and DENZO, DENZO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O20.87 (2)2.12 (2)2.975 (2)170.0 (19)
N2—H1N···O2i0.93 (2)2.12 (2)2.948 (2)147.6 (17)
N3—H4N···O10.94 (2)1.99 (2)2.924 (2)172.2 (19)
N3—H3N···O1ii0.88 (2)2.10 (2)2.945 (2)159.7 (18)
Symmetry codes: (i) x+1, y, z+2; (ii) x+1, y, z+1.
 

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