Competing hydrogen-bonding patterns and phase transitions of 1,2-diaminoethane at varied temperature and pressure

1,2-Diaminoethane has been in-situ pressure- and temperature-frozen; apart from two known low-temperature phases, Iα and II, three new phases, Iβ, Iγ and III, have been observed and their structures determined by X-ray diffraction. The measurements at 0.1 MPa were carried out at 274, 243 and 224 K, and 296 K measurements were made at 0.15 GPa (phase Iα), at 0.3 and 1.1 GPa (phase Iβ), at 1.5 GPa (phase Iγ), and at 0.2, 0.3 and 0.5 GPa (phase III). All these phases are monoclinic, space group P2₁/c, but the unit-cell dimension of phases Iα and III are very different at 296 K: a_Iα = 5.078 (5), b_Iα = 7.204 (8), c_Iα = 5.528 (20) Å, β_Iα = 115.2 (2)° at 0.15 GPa, and a_III = 5.10 (3), b_III = 5.212 (2), c_III = 7.262 (12) Å, β_III = 111.6 (4)° at 0.2 GPa, respectively; in both phases Z = 2. An ambient-pressure low-temperature phase II has been observed below 189 K. Discontinuities in the unit-cell dimensions and in the N...N distance mark the isostructural transition between phases Iα and Iβ at 0.2 GPa, which can be attributed to a damping process of the NH₂ group rotations. In phase Iγ the unit-cell parameter a doubles and Z increases to 4. The molecule has inversion symmetry in all the structures determined. 1,2-Diaminoethane can be considered as a simple structural ice analogue, but with NH...N hydrogen bonds and with the H-atom donors (four in one molecule) in excess over H-atom acceptors (two per molecule). Thus, the transformations of 1,2-diaminoethane phases involving the conformational dynamics affect the hydrogen-bonding geometry and molecular association in the crystal. The 1,2-diaminoethane:1,2-dihydroxyethane mixture has been separated by pressure-freezing, and a solid 1,2-diaminoethane crystal in liquid 1,2-dihyroxyethane has been obtained.

Computing details

For all compounds, data collection: CrysAlis (Oxford Diffraction, 2002); cell refinement: CrysAlis (Oxford Diffraction, 2002); data reduction: CrysAlis (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001)

and POV-RAY (Persistence of Vision, 2004); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

(DAE224K) 1,2-diaminoethane phase I alpha

Crystal data

C2H8N2	F(000) = 68
Mr = 60.10	Dx = 1.100 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.065 (1) Å	Cell parameters from 457 reflections
b = 7.181 (1) Å	θ = 4.4–29.1°
c = 5.508 (1) Å	µ = 0.07 mm^−1
β = 115.07 (3)°	T = 224 K
V = 181.46 (7) Å^3	Plate, colourless
Z = 2	0.6 × 0.4 × 0.1 mm

Data collection

Kuma KM4CCD κ geometry diffractometer	369 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.061
Graphite monochromator	θmax = 29.1°, θmin = 4.4°
ω scans	h = −6→6
1070 measured reflections	k = −8→9
457 independent reflections	l = −7→7

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)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0726P)^2 + 0.0014P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
457 reflections	Δρmax = 0.31 e Å^−3
25 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.33 (14)

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
N1	0.8524 (2)	0.36693 (15)	0.21202 (19)	0.0300 (4)
H1	0.9814	0.4725	0.2722	0.036*
H2	0.8806	0.3101	0.0775	0.036*
C1	0.5496 (2)	0.43086 (17)	0.1161 (2)	0.0257 (4)
H4	0.5252	0.4882	0.2647	0.038 (4)*
H3	0.4225	0.3230	0.0606	0.033 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0290 (7)	0.0326 (7)	0.0281 (6)	0.0037 (4)	0.0117 (5)	0.0029 (4)
C1	0.0283 (7)	0.0252 (7)	0.0259 (6)	−0.0004 (4)	0.0137 (5)	0.0025 (4)

Geometric parameters (Å, º)

N1—C1	1.4682 (15)	C1—C1^i	1.526 (2)
N1—H1	0.9634	C1—H4	0.9700
N1—H2	0.9084	C1—H3	0.9700
C1—N1—H1	109.3	C1^i—C1—H4	108.4
C1—N1—H2	110.4	N1—C1—H3	108.4
H1—N1—H2	108.4	C1^i—C1—H3	108.4
N1—C1—C1^i	115.33 (12)	H4—C1—H3	107.5
N1—C1—H4	108.4

Symmetry code: (i) −x+1, −y+1, −z.

(DAE243K) 1,2-diaminoethane phase I alpha

Crystal data

C2H8N2	Dx = 1.100 Mg m^−3
Mr = 60.10	Melting point: 284.29 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.070 (1) Å	Cell parameters from 866 reflections
b = 7.185 (1) Å	θ = 4.4–29.1°
c = 5.501 (1) Å	µ = 0.07 mm^−1
β = 115.11 (3)°	T = 243 K
V = 181.45 (7) Å^3	Plate, colourless
Z = 2	0.6 × 0.4 × 0.1 mm
F(000) = 68

Data collection

Kuma KM4CCD κ geometry diffractometer	406 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 29.1°, θmin = 4.4°
ω scans	h = −6→6
1241 measured reflections	k = −8→9
458 independent reflections	l = −7→6

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.0216P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
458 reflections	Δρmax = 0.34 e Å^−3
25 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.38 (11)

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
N1	0.85189 (18)	0.36691 (12)	0.21189 (17)	0.0296 (4)
H1	0.8814	0.3078	0.0682	0.036*
H2	0.9720	0.4671	0.2683	0.036*
C1	0.5496 (2)	0.43080 (13)	0.11635 (18)	0.0252 (4)
H4	0.5256	0.4882	0.2653	0.035 (3)*
H3	0.4224	0.3231	0.0607	0.034 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0281 (5)	0.0328 (6)	0.0269 (5)	0.0032 (3)	0.0107 (4)	0.0034 (3)
C1	0.0282 (6)	0.0250 (5)	0.0242 (5)	0.0001 (3)	0.0128 (4)	0.0024 (3)

Geometric parameters (Å, º)

N1—C1	1.4672 (13)	C1—C1^i	1.5277 (18)
N1—H1	0.9631	C1—H4	0.9700
N1—H2	0.9084	C1—H3	0.9700
C1—N1—H1	110.3	C1^i—C1—H4	108.5
C1—N1—H2	108.7	N1—C1—H3	108.5
H1—N1—H2	108.4	C1^i—C1—H3	108.5
N1—C1—C1^i	115.22 (9)	H4—C1—H3	107.5
N1—C1—H4	108.5

Symmetry code: (i) −x+1, −y+1, −z.

(DAE274K) 1,2-diaminoethane phase I alpha

Crystal data

C2H8N2	F(000) = 68
Mr = 60.10	Dx = 1.085 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.102 (1) Å	Cell parameters from 240 reflections
b = 7.197 (1) Å	θ = 4.4–28.6°
c = 5.535 (1) Å	µ = 0.07 mm^−1
β = 115.18 (3)°	T = 274 K
V = 183.93 (7) Å^3	Plate, colourless
Z = 2	0.6 × 0.4 × 0.1 mm

Data collection

Kuma KM4CCD κ geometry diffractometer	330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.129
Graphite monochromator	θmax = 28.6°, θmin = 4.4°
ω scans	h = −6→6
940 measured reflections	k = −8→9
452 independent reflections	l = −7→6

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)] = 0.085	H-atom parameters constrained
wR(F^2) = 0.210	w = 1/[σ^2(Fo^2) + (0.1384P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
452 reflections	Δρmax = 0.35 e Å^−3
25 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.6 (3)

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
N1	0.8483 (3)	0.3676 (2)	0.2102 (3)	0.0444 (7)
H1	0.9857	0.4683	0.2801	0.053*
H2	0.8744	0.3138	0.0727	0.053*
C1	0.5494 (3)	0.4318 (2)	0.1156 (3)	0.0380 (7)
H4	0.5265	0.4899	0.2636	0.039 (4)*
H3	0.4226	0.3244	0.0615	0.052 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0385 (11)	0.0432 (11)	0.0442 (10)	0.0051 (6)	0.0106 (7)	0.0048 (6)
C1	0.0388 (11)	0.0318 (10)	0.0404 (10)	−0.0011 (6)	0.0140 (7)	0.0030 (6)

Geometric parameters (Å, º)

N1—C1	1.461 (2)	C1—C1^i	1.519 (3)
N1—H1	0.9670	C1—H4	0.9700
N1—H2	0.9127	C1—H3	0.9700
C1—N1—H1	112.0	C1^i—C1—H4	108.4
C1—N1—H2	109.6	N1—C1—H3	108.4
H1—N1—H2	108.2	C1^i—C1—H3	108.4
N1—C1—C1^i	115.35 (18)	H4—C1—H3	107.5
N1—C1—H4	108.4

Symmetry code: (i) −x+1, −y+1, −z.

(DAE015G) 1,2-diaminoethane phase I alpha

Crystal data

C2H8N2	The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication
Mr = 60.10	Dx = 1.091 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.078 (5) Å	Cell parameters from 355 reflections
b = 7.204 (8) Å	θ = 4.4–29.6°
c = 5.528 (12) Å	µ = 0.07 mm^−1
β = 115.24 (18)°	T = 296 K
V = 182.9 (6) Å^3	, colourless
Z = 2	0.30 × 0.30 × 0.08 mm
F(000) = 68

Data collection

Kuma KM4CCD κ geometry diffractometer	224 independent reflections
Radiation source: fine-focus sealed tube	188 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 16.4 pixels mm^-1	θmax = 29.6°, θmin = 4.4°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −6→6
Absorption correction: integration Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467	k = −8→8
Tmin = 0.44, Tmax = 0.84	l = −5→5
1259 measured reflections

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)] = 0.084	H-atom parameters constrained
wR(F^2) = 0.130	w = 1/[σ^2(Fo^2) + (0.P)^2 + 0.1653P] where P = (Fo^2 + 2Fc^2)/3
S = 1.25	(Δ/σ)max < 0.001
224 reflections	Δρmax = 0.10 e Å^−3
25 parameters	Δρmin = −0.11 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 1.00 (13)

Special details

Experimental. high-pressure measurement at 0.15 (5) GPa - the high pressure of ethylenodiamine

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
N1	0.8491 (8)	0.3686 (5)	0.2117 (10)	0.0493 (14)
H1	0.9739	0.4767	0.2550	0.059*
H2	0.8699	0.3049	0.0787	0.059*
C1	0.5489 (7)	0.4333 (6)	0.1154 (11)	0.0423 (14)
H4	0.5257	0.4926	0.2627	0.057 (13)*
H3	0.4211	0.3261	0.0623	0.032 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0464 (19)	0.060 (3)	0.039 (4)	0.0037 (15)	0.0158 (19)	0.0043 (15)
C1	0.047 (2)	0.048 (4)	0.034 (5)	−0.0048 (17)	0.019 (2)	0.0019 (15)

Geometric parameters (Å, º)

N1—C1	1.461 (5)	C1—C1^i	1.503 (9)
N1—H1	0.9673	C1—H4	0.9700
N1—H2	0.9100	C1—H3	0.9700
C1—N1—H1	107.8	C1^i—C1—H4	108.4
C1—N1—H2	109.2	N1—C1—H3	108.4
H1—N1—H2	108.5	C1^i—C1—H3	108.4
N1—C1—C1^i	115.4 (5)	H4—C1—H3	107.5
N1—C1—H4	108.4

Symmetry code: (i) −x+1, −y+1, −z.

(DAE03G1) 1,2-diaminoethane phase I beta

Crystal data

C2H8N2	The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication
Mr = 60.10	Dx = 1.182 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.949 (6) Å	Cell parameters from 343 reflections
b = 7.704 (8) Å	θ = 5.3–28.9°
c = 4.96 (3) Å	µ = 0.08 mm^−1
β = 116.7 (11)°	T = 296 K
V = 169.0 (19) Å^3	, colourless
Z = 2	0.42 × 0.42 × 0.10 mm
F(000) = 68

Data collection

Kuma KM4CCD κ geometry diffractometer	117 independent reflections
Radiation source: fine-focus sealed tube	113 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
Detector resolution: 16.4 pixels mm^-1	θmax = 28.9°, θmin = 5.3°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −3→3
Absorption correction: integration Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467	k = −10→10
Tmin = 0.48, Tmax = 0.94	l = −6→6
1260 measured reflections

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)] = 0.142	H-atom parameters constrained
wR(F^2) = 0.266	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.3P] where P = (Fo^2 + 2Fc^2)/3
S = 1.76	(Δ/σ)max < 0.001
117 reflections	Δρmax = 0.12 e Å^−3
20 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.3 (2)

Special details

Experimental. high-pressure measurement at 0.30 (5) GPa - the high pressure of ethylenodiamine

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
N1	0.777 (5)	0.3540 (11)	0.276 (3)	0.045 (3)*
H1	0.8596	0.3022	0.1628	0.054*
H2	0.9307	0.3962	0.4451	0.054*
C1	0.501 (7)	0.4352 (12)	0.112 (3)	0.05 (2)
H4	0.4423	0.4927	0.2512	0.05 (2)*
H3	0.3500	0.3472	0.0054	0.11 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.07 (7)	0.042 (5)	0.050 (15)	0.005 (11)	0.03 (3)	−0.002 (6)

Geometric parameters (Å, º)

N1—C1	1.39 (4)	C1—C1^i	1.487 (18)
N1—H1	0.9174	C1—H4	0.9700
N1—H2	0.9023	C1—H3	0.9700
C1—N1—H1	115.4	C1^i—C1—H4	108.7
C1—N1—H2	125.4	N1—C1—H3	108.7
H1—N1—H2	107.9	C1^i—C1—H3	108.7
N1—C1—C1^i	114 (3)	H4—C1—H3	107.6
N1—C1—H4	108.7

Symmetry code: (i) −x+1, −y+1, −z.

(DAE11G) 1,2-diaminoethane phase I beta

Crystal data

C2H8N2	The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication
Mr = 60.10	Dx = 1.236 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.82 (5) Å	Cell parameters from 510 reflections
b = 7.563 (5) Å	θ = 5.3–29.4°
c = 4.873 (18) Å	µ = 0.08 mm^−1
β = 114.5 (8)°	T = 296 K
V = 162 (2) Å^3	, colourless
Z = 2	0.41 × 0.41 × 0.09 mm
F(000) = 68

Data collection

Kuma KM4CCD κ geometry diffractometer	124 independent reflections
Radiation source: fine-focus sealed tube	103 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 16.4 pixels mm^-1	θmax = 29.4°, θmin = 5.3°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −3→3
Absorption correction: integration Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467	k = −10→10
Tmin = 0.45, Tmax = 0.93	l = −6→6
1159 measured reflections

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)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.212	w = 1/[σ^2(Fo^2) + (0.1176P)^2 + 0.1743P] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
124 reflections	Δρmax = 0.10 e Å^−3
25 parameters	Δρmin = −0.10 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 1.0 (6)

Special details

Experimental. high-pressure measurement at 1.10 (5) GPa - the high pressure of ethylenodiamine

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
N1	0.794 (3)	0.3522 (6)	0.2867 (16)	0.071 (10)
H1	0.8436	0.2967	0.1520	0.085*
H2	0.9550	0.4152	0.4101	0.085*
C1	0.495 (4)	0.4306 (7)	0.1128 (19)	0.055 (13)
H4	0.4213	0.4857	0.2498	0.059 (15)*
H3	0.3521	0.3380	0.0041	0.10 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.11 (3)	0.047 (2)	0.070 (7)	0.014 (5)	0.052 (13)	0.014 (2)
C1	0.08 (4)	0.045 (3)	0.053 (7)	−0.005 (5)	0.039 (16)	−0.007 (3)

Geometric parameters (Å, º)

N1—C1	1.46 (3)	C1—C1^i	1.536 (11)
N1—H1	0.8923	C1—H4	0.9700
N1—H2	0.8967	C1—H3	0.9700
C1—N1—H1	105.4	C1^i—C1—H4	109.2
C1—N1—H2	123.0	N1—C1—H3	109.2
H1—N1—H2	108.6	C1^i—C1—H3	109.2
N1—C1—C1^i	112.1 (18)	H4—C1—H3	107.9
N1—C1—H4	109.2

Symmetry code: (i) −x+1, −y+1, −z.

(DAE15G) 1,2-diaminoethane phase I gamma

Crystal data

C2H8N2	The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication
Mr = 60.10	Dx = 1.243 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.69 (10) Å	Cell parameters from 516 reflections
b = 7.488 (5) Å	θ = 5.0–29.8°
c = 4.849 (14) Å	µ = 0.08 mm^−1
β = 114.0 (7)°	T = 296 K
V = 321 (4) Å^3	, colourless
Z = 4	0.41 × 0.41 × 0.08 mm
F(000) = 136

Data collection

Kuma KM4CCD κ geometry diffractometer	235 independent reflections
Radiation source: fine-focus sealed tube	225 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.108
Detector resolution: 16.4 pixels mm^-1	θmax = 29.8°, θmin = 5.0°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −5→5
Absorption correction: integration Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467	k = −10→10
Tmin = 0.45, Tmax = 0.93	l = −6→6
2437 measured reflections

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)] = 0.237	H-atom parameters constrained
wR(F^2) = 0.433	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 5.P] where P = (Fo^2 + 2Fc^2)/3
S = 1.39	(Δ/σ)max < 0.001
235 reflections	Δρmax = 0.33 e Å^−3
26 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.8 (3)

Special details

Experimental. high-pressure measurement at 1.50 (5) GPa - the high pressure of ethylenodiamine

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
N1	0.144 (4)	0.3449 (13)	0.275 (3)	0.012 (3)*
H1	0.1350	0.2312	0.3093	0.014*
H2	0.2069	0.3559	0.1780	0.014*
C1	−0.004 (7)	0.436 (2)	0.105 (5)	0.037 (5)*
H3	−0.0352	0.4949	0.2479	0.045*
H4	−0.0791	0.3469	−0.0018	0.045*
N2	0.651 (5)	0.3723 (17)	0.317 (4)	0.036 (5)*
H7	0.6942	0.3060	0.2219	0.043*
H8	0.6699	0.3212	0.4965	0.043*
C2	0.503 (6)	0.4301 (18)	0.118 (5)	0.029 (5)*
H5	0.4531	0.4790	0.2386	0.035*
H6	0.4456	0.3264	0.0127	0.035*

Geometric parameters (Å, º)

N1—C1	1.49 (6)	N2—C2	1.43 (6)
N1—H1	0.8791	N2—H7	0.8906
N1—H2	0.9119	N2—H8	0.8984
C1—C1^i	1.42 (3)	C2—C2^ii	1.53 (3)
C1—H3	0.9700	C2—H5	0.9700
C1—H4	0.9700	C2—H6	0.9700
C1—N1—H1	113.6	C2—N2—H7	111.9
C1—N1—H2	111.5	C2—N2—H8	122.4
H1—N1—H2	108.9	H7—N2—H8	108.1
N1—C1—C1^i	113 (6)	N2—C2—C2^ii	116 (6)
N1—C1—H3	109.0	N2—C2—H5	108.4
C1^i—C1—H3	109.0	C2^ii—C2—H5	108.4
N1—C1—H4	109.0	N2—C2—H6	108.4
C1^i—C1—H4	109.0	C2^ii—C2—H6	108.4
H3—C1—H4	107.8	H5—C2—H6	107.4

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

(DAE02G) 1,2-diaminoethane phase II

Crystal data

C2H8N2	The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication
Mr = 60.10	Dx = 1.113 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.10 (3) Å	Cell parameters from 794 reflections
b = 5.212 (2) Å	θ = 4.9–29.3°
c = 7.262 (12) Å	µ = 0.08 mm^−1
β = 111.6 (4)°	T = 296 K
V = 179.5 (12) Å^3	, colourless
Z = 2	0.42 × 0.42 × 0.11 mm
F(000) = 68

Data collection

Kuma KM4CCD κ geometry diffractometer	141 independent reflections
Radiation source: fine-focus sealed tube	125 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
Detector resolution: 16.4 pixels mm^-1	θmax = 29.3°, θmin = 4.9°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −3→3
Absorption correction: integration Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467	k = −7→7
Tmin = 0.47, Tmax = 0.89	l = −9→9
1272 measured reflections

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)] = 0.055	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0185P)^2 + 0.1484P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
141 reflections	Δρmax = 0.10 e Å^−3
25 parameters	Δρmin = −0.09 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 10.4 (13)

Special details

Experimental. high-pressure measurement at 0.20 (5) GPa - the high pressure of ethylenodiamine

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
N1	0.824 (3)	0.7076 (8)	0.6248 (9)	0.060 (9)
H1	0.9058	0.7499	0.5280	0.072*
H2	0.9338	0.5602	0.6780	0.072*
C1	0.536 (3)	0.6165 (8)	0.5673 (10)	0.067 (10)
H3	0.4094	0.7550	0.5009	0.046 (16)*
H4	0.5008	0.5752	0.6864	0.030 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.09 (3)	0.038 (2)	0.049 (5)	−0.004 (5)	0.026 (11)	−0.006 (2)
C1	0.14 (3)	0.026 (2)	0.049 (5)	0.004 (5)	0.053 (12)	0.000 (2)

Geometric parameters (Å, º)

N1—C1	1.45 (2)	C1—C1^i	1.517 (10)
N1—H1	0.9644	C1—H3	0.9700
N1—H2	0.9443	C1—H4	0.9700
C1—N1—H1	121.9	C1^i—C1—H3	108.5
C1—N1—H2	103.6	N1—C1—H4	108.5
H1—N1—H2	97.8	C1^i—C1—H4	108.5
N1—C1—C1^i	115.2 (14)	H3—C1—H4	107.5
N1—C1—H3	108.5

Symmetry code: (i) −x+1, −y+1, −z+1.

(DAE03G2) 1,2-diaminoethane phase II

Crystal data

C2H8N2	The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication
Mr = 60.10	Dx = 1.152 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.031 (10) Å	Cell parameters from 697 reflections
b = 5.132 (3) Å	θ = 5.0–29.4°
c = 7.167 (5) Å	µ = 0.08 mm^−1
β = 110.60 (12)°	T = 296 K
V = 173.2 (4) Å^3	, colourless
Z = 2	0.40 × 0.40 × 0.09 mm
F(000) = 68

Data collection

Kuma KM4CCD κ geometry diffractometer	96 independent reflections
Radiation source: fine-focus sealed tube	72 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.091
Detector resolution: 16.4 pixels mm^-1	θmax = 29.4°, θmin = 5.0°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −3→3
Absorption correction: integration Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467	k = −6→6
Tmin = 0.55, Tmax = 0.91	l = −9→9
897 measured reflections

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)] = 0.074	H-atom parameters constrained
wR(F^2) = 0.253	w = 1/[σ^2(Fo^2) + (0.1848P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.22	(Δ/σ)max < 0.001
96 reflections	Δρmax = 0.15 e Å^−3
20 parameters	Δρmin = −0.14 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.3 (4)

Special details

Experimental. high-pressure measurement at 0.30 (5) GPa - the high pressure of ethylenodiamine

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
N1	0.820 (6)	0.7126 (10)	0.6209 (18)	0.11 (2)
H1	0.8483	0.7223	0.4970	0.138*
H2	0.9604	0.5891	0.6817	0.138*
C1	0.542 (5)	0.6209 (14)	0.5720 (15)	0.043 (3)*
H3	0.4128	0.7625	0.5109	0.18 (11)*
H4	0.5124	0.5753	0.6946	0.027 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.25 (6)	0.036 (3)	0.097 (12)	−0.008 (10)	0.11 (3)	−0.002 (4)

Geometric parameters (Å, º)

N1—C1	1.40 (4)	C1—C1^i	1.574 (19)
N1—H1	0.9479	C1—H3	0.9700
N1—H2	0.9334	C1—H4	0.9700
C1—N1—H1	104.4	C1^i—C1—H3	108.2
C1—N1—H2	114.4	N1—C1—H4	108.2
H1—N1—H2	97.9	C1^i—C1—H4	108.2
N1—C1—C1^i	116 (2)	H3—C1—H4	107.4
N1—C1—H3	108.2

Symmetry code: (i) −x+1, −y+1, −z+1.

(DAE05G) 1,2-diaminoethane phase II

Crystal data

C2H8N2	The unit-cell dimensions corrected for the effect of the gasket-shadowing: Katrusiak Andrzej - being prepared for publication
Mr = 60.10	Dx = 1.157 Mg m^−3
Monoclinic, P21/c	Melting point: 284.29 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.9921 (18) Å	Cell parameters from 761 reflections
b = 5.137 (4) Å	θ = 4.4–29.9°
c = 7.200 (4) Å	µ = 0.08 mm^−1
β = 110.87 (5)°	T = 296 K
V = 172.53 (19) Å^3	, colourless
Z = 2	0.35 × 0.35 × 0.08 mm
F(000) = 68

Data collection

Kuma KM4CCD κ geometry diffractometer	206 independent reflections
Radiation source: fine-focus sealed tube	193 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 16.4 pixels mm^-1	θmax = 29.9°, θmin = 4.4°
HP ω scans – for more details see: A. Budzianowski, A. Katrusiak in High–Pressure Crystallography (Eds.: A. Katrusiak, P. F. McMillan), Dordrecht: Kluwer Acad. Publ., 2004 pp.157–168	h = −6→6
Absorption correction: integration Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467	k = −4→4
Tmin = 0.49, Tmax = 0.82	l = −8→8
1110 measured reflections

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)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.1608P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
206 reflections	Δρmax = 0.13 e Å^−3
25 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.3 (2)

Special details

Experimental. high-pressure measurement at 0.50 (5) GPa - the high pressure of ethylenodiamine

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
N1	0.8294 (5)	0.7134 (7)	0.6240 (4)	0.0389 (11)
H1	0.8702	0.7232	0.5052	0.047*
H2	0.9595	0.5829	0.6877	0.047*
C1	0.5352 (6)	0.6194 (9)	0.5681 (5)	0.0305 (11)
H3	0.4060	0.7593	0.5019	0.049 (10)*
H4	0.4988	0.5771	0.6882	0.034 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0366 (14)	0.028 (3)	0.049 (2)	−0.0029 (13)	0.0115 (11)	−0.0056 (10)
C1	0.0351 (14)	0.021 (4)	0.035 (3)	0.0021 (12)	0.0114 (12)	−0.0012 (9)

Geometric parameters (Å, º)

N1—C1	1.460 (4)	C1—C1^i	1.531 (6)
N1—H1	0.9483	C1—H3	0.9700
N1—H2	0.9324	C1—H4	0.9700
C1—N1—H1	106.7	C1^i—C1—H3	108.5
C1—N1—H2	110.7	N1—C1—H4	108.5
H1—N1—H2	98.4	C1^i—C1—H4	108.5
N1—C1—C1^i	114.9 (3)	H3—C1—H4	107.5
N1—C1—H3	108.5

Symmetry code: (i) −x+1, −y+1, −z+1.