Temperature dependence of the crystal structure of 3,5-di-tert-butylpyrazole from 10 K

A single crystal of 3,5-di-tert-butylpyrazole has been the subject of structure determinations at 10, 100, 120 and 299 K. Above ∼ 110 K, the structure is Pbca, a ≃ 11.3, b ≃ 20.6, c ≃ 10 Å, Z = 8. Below 110 K, the c axis is doubled and the space group becomes Pb2₁a, Z = 16. Here the asymmetric unit is comprised of four molecules, arranged as a pair of overlapping hydrogen-bonded dimers, all components being ordered. In each case one methyl group of each t-butyl group lies coplanar with its parent pyrazole ring and, within each quasi-inversion-related dimer, one molecule has both of these methyl groups directed away from the N₂ component `cis', while in the other, one methyl group is toward (`trans'). Above 110 K the four molecules collapse into one, with one t-butyl group (corresponding to an overlaid `cis/trans' pair of the low-temperature form) modelled as disordered. The disorder has been previously described as `temperature dependent' (Deacon et al., 2001), but the present studies suggest it to be dependent on the history of the particular specimen as well.

Computing details

For all compounds, data collection: Local diffractometer control software; cell refinement: Local diffractometer control software; data reduction: PROFIT (Streltsov & Zavodnik, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker,1997); software used to prepare material for publication: SHELXTL (Bruker,1997).

Figures

(10k)

Crystal data

C11H20N2	F(000) = 1600
Mr = 180.29	Dx = 1.053 Mg m^−3
Orthorhombic, Pb21a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2a -2ab	Cell parameters from 14 reflections
a = 11.279 (2) Å	θ = 16.0–20.1°
b = 20.634 (4) Å	µ = 0.06 mm^−1
c = 19.542 (4) Å	T = 10 K
V = 4548.0 (15) Å^3	Prism, colourless
Z = 16	0.44 × 0.34 × 0.20 mm

Data collection

Huber 512 goniometer diffractometer	3744 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.070
None monochromator	θmax = 25.0°, θmin = 2.0°
ω–2θ scan	h = −13→13
Absorption correction: gaussian Xtal 3.7 (Hall, du Boulay & Olthof-Hazekamp, 2000)	k = −24→24
Tmin = 0.980, Tmax = 0.988	l = −23→23
15825 measured reflections	3 standard reflections every 100 reflections
4162 independent reflections	intensity decay: 2%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0639P)^2 + 0.7985P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max = 0.044
S = 1.07	Δρmax = 0.28 e Å^−3
4162 reflections	Δρmin = −0.21 e Å^−3
742 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0012 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0 (3)

Special details

Experimental. The correction for the absorption by the beryllium shield was performed by PROFIT (Streltsov & Zavodnik, 1989) program.

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
N1A	0.3975 (2)	0.05543 (13)	0.64854 (13)	0.0106 (5)
H1A	0.417 (3)	0.018 (2)	0.6607 (17)	0.009 (9)*
N2A	0.4735 (2)	0.08368 (13)	0.60251 (12)	0.0108 (5)
C3A	0.4269 (3)	0.14222 (14)	0.59128 (15)	0.0098 (6)
C31A	0.4872 (3)	0.18877 (14)	0.54217 (15)	0.0111 (6)
C32A	0.4200 (3)	0.25339 (15)	0.53979 (16)	0.0127 (7)
H31A	0.412 (3)	0.2746 (18)	0.5837 (19)	0.013 (5)*
H32A	0.337 (3)	0.2474 (16)	0.5272 (17)	0.013 (5)*
H33A	0.458 (3)	0.2866 (17)	0.5082 (18)	0.013 (5)*
C33A	0.6150 (3)	0.20088 (16)	0.56532 (17)	0.0145 (7)
H34A	0.620 (3)	0.2170 (19)	0.613 (2)	0.019 (5)*
H35A	0.655 (3)	0.231 (2)	0.5367 (18)	0.019 (5)*
H36A	0.665 (3)	0.163 (2)	0.5665 (19)	0.019 (5)*
C34A	0.4892 (3)	0.15885 (15)	0.46930 (16)	0.0145 (7)
H37A	0.411 (3)	0.1540 (16)	0.4558 (17)	0.009 (5)*
H38A	0.532 (3)	0.1172 (17)	0.4703 (17)	0.009 (5)*
H39A	0.533 (3)	0.1899 (16)	0.4374 (17)	0.009 (5)*
C4A	0.3220 (3)	0.15038 (15)	0.62974 (15)	0.0106 (6)
H4A	0.270 (3)	0.1874 (18)	0.6284 (17)	0.014 (9)*
C5A	0.3063 (3)	0.09375 (14)	0.66589 (15)	0.0112 (6)
C51A	0.2130 (3)	0.07193 (14)	0.71673 (15)	0.0113 (6)
C52A	0.1214 (3)	0.12574 (15)	0.72659 (15)	0.0146 (6)
H51A	0.162 (3)	0.1630 (18)	0.7435 (16)	0.012 (5)*
H52A	0.058 (3)	0.1114 (16)	0.7590 (17)	0.012 (5)*
H53A	0.079 (3)	0.1354 (17)	0.6811 (18)	0.012 (5)*
C53A	0.1502 (3)	0.01030 (15)	0.68978 (16)	0.0161 (6)
H54A	0.104 (3)	0.0214 (18)	0.6447 (18)	0.019 (5)*
H55A	0.089 (3)	−0.0028 (18)	0.7248 (17)	0.019 (5)*
H56A	0.212 (3)	−0.0232 (18)	0.6794 (17)	0.019 (5)*
C54A	0.2718 (3)	0.05619 (16)	0.78554 (14)	0.0144 (6)
H57A	0.317 (3)	0.0927 (19)	0.8022 (19)	0.017 (5)*
H58A	0.327 (3)	0.0202 (18)	0.7824 (17)	0.017 (5)*
H59A	0.210 (3)	0.0469 (17)	0.8179 (17)	0.017 (5)*
N1B	0.5905 (2)	−0.03953 (13)	0.60052 (13)	0.0096 (5)
H1B	0.573 (3)	0.002 (2)	0.5880 (17)	0.016 (9)*
N2B	0.5171 (2)	−0.06689 (12)	0.64791 (12)	0.0094 (5)
C3B	0.5644 (3)	−0.12561 (14)	0.66018 (15)	0.0099 (6)
C31B	0.5052 (3)	−0.17053 (14)	0.71131 (16)	0.0118 (6)
C32B	0.5774 (3)	−0.23330 (15)	0.71769 (17)	0.0143 (7)
H31B	0.574 (3)	−0.2597 (18)	0.6726 (19)	0.015 (5)*
H32B	0.540 (3)	−0.2627 (18)	0.7505 (18)	0.015 (5)*
H33B	0.658 (3)	−0.2243 (18)	0.7337 (18)	0.015 (5)*
C33B	0.4994 (3)	−0.13707 (16)	0.78172 (17)	0.0192 (7)
H34B	0.447 (3)	−0.0956 (19)	0.7826 (19)	0.022 (5)*
H35B	0.581 (3)	−0.1255 (18)	0.7969 (19)	0.022 (5)*
H36B	0.456 (3)	−0.1659 (18)	0.8157 (19)	0.022 (5)*
C34B	0.3788 (3)	−0.18629 (16)	0.68731 (17)	0.0160 (7)
H37B	0.389 (3)	−0.208 (2)	0.642 (2)	0.022 (6)*
H38B	0.325 (3)	−0.1444 (19)	0.6837 (19)	0.022 (6)*
H39B	0.338 (3)	−0.2186 (19)	0.7221 (19)	0.022 (6)*
C4B	0.6668 (3)	−0.13487 (15)	0.62063 (15)	0.0116 (6)
H4B	0.718 (3)	−0.173 (2)	0.6200 (18)	0.018 (9)*
C5B	0.6815 (3)	−0.07810 (14)	0.58314 (15)	0.0106 (6)
C51B	0.7759 (3)	−0.05755 (14)	0.53221 (15)	0.0113 (6)
C52B	0.7590 (3)	0.01342 (14)	0.51219 (15)	0.0162 (6)
H51B	0.764 (3)	0.0427 (19)	0.5508 (18)	0.021 (5)*
H52B	0.677 (3)	0.0197 (17)	0.4875 (18)	0.021 (5)*
H53B	0.827 (3)	0.0275 (17)	0.4805 (18)	0.021 (5)*
C53B	0.8988 (3)	−0.06639 (18)	0.56446 (16)	0.0193 (7)
H54B	0.910 (3)	−0.0390 (19)	0.607 (2)	0.023 (6)*
H55B	0.961 (3)	−0.0523 (18)	0.5353 (18)	0.023 (6)*
H56B	0.907 (3)	−0.110 (2)	0.5796 (19)	0.023 (6)*
C54B	0.7672 (3)	−0.10044 (15)	0.46824 (15)	0.0151 (6)
H57B	0.695 (4)	−0.0956 (19)	0.445 (2)	0.022 (5)*
H58B	0.783 (3)	−0.1482 (19)	0.4789 (18)	0.022 (5)*
H59B	0.833 (3)	−0.0911 (17)	0.4372 (19)	0.022 (5)*
N1C	0.6002 (2)	−0.05592 (12)	0.10010 (13)	0.0101 (5)
H1C	0.579 (3)	−0.017 (2)	0.0884 (19)	0.021 (10)*
N2C	0.5290 (2)	−0.08397 (12)	0.14793 (12)	0.0100 (5)
C3C	0.5700 (3)	−0.14497 (14)	0.15344 (14)	0.0105 (6)
C31C	0.5087 (3)	−0.19287 (15)	0.20088 (15)	0.0108 (6)
C32C	0.5789 (3)	−0.25621 (15)	0.20347 (17)	0.0143 (7)
H31C	0.666 (3)	−0.2491 (19)	0.2202 (19)	0.021 (6)*
H32C	0.585 (3)	−0.2765 (19)	0.158 (2)	0.021 (6)*
H33C	0.538 (3)	−0.2864 (19)	0.2331 (19)	0.021 (6)*
C33C	0.4995 (3)	−0.16392 (16)	0.27305 (16)	0.0145 (7)
H34C	0.579 (3)	−0.1560 (19)	0.2932 (19)	0.025 (6)*
H35C	0.460 (3)	−0.1961 (19)	0.304 (2)	0.025 (6)*
H36C	0.450 (4)	−0.125 (2)	0.273 (2)	0.025 (6)*
C34C	0.3836 (3)	−0.20687 (15)	0.17358 (16)	0.0138 (7)
H37C	0.386 (3)	−0.2274 (18)	0.1294 (19)	0.017 (5)*
H38C	0.333 (3)	−0.1621 (18)	0.1729 (18)	0.017 (5)*
H39C	0.335 (3)	−0.2397 (18)	0.2022 (18)	0.017 (5)*
C4C	0.6666 (3)	−0.15463 (14)	0.10885 (15)	0.0106 (6)
H4C	0.712 (3)	−0.1915 (16)	0.1035 (15)	0.000 (7)*
C5C	0.6835 (3)	−0.09632 (14)	0.07554 (15)	0.0103 (6)
C51C	0.7692 (3)	−0.07547 (14)	0.01978 (14)	0.0108 (6)
C52C	0.8642 (3)	−0.12773 (15)	0.01055 (15)	0.0146 (6)
H51C	0.910 (3)	−0.1359 (18)	0.0514 (19)	0.019 (5)*
H52C	0.919 (3)	−0.1141 (17)	−0.0258 (18)	0.019 (5)*
H53C	0.825 (3)	−0.1708 (17)	−0.0037 (18)	0.019 (5)*
C53C	0.7007 (3)	−0.06755 (16)	−0.04774 (15)	0.0156 (6)
H54C	0.637 (3)	−0.0373 (19)	−0.0432 (18)	0.024 (5)*
H55C	0.659 (3)	−0.109 (2)	−0.0597 (19)	0.024 (5)*
H56C	0.757 (3)	−0.0557 (18)	−0.0853 (18)	0.024 (5)*
C54C	0.8286 (3)	−0.01101 (15)	0.03938 (16)	0.0157 (6)
H57C	0.884 (3)	−0.0186 (18)	0.0808 (19)	0.018 (5)*
H58C	0.770 (3)	0.0218 (18)	0.0435 (17)	0.018 (5)*
H59C	0.883 (3)	0.0017 (17)	0.0044 (18)	0.018 (5)*
N1D	0.4149 (2)	0.04003 (12)	0.15261 (13)	0.0099 (5)
H1D	0.429 (4)	0.000 (2)	0.163 (2)	0.031 (11)*
N2D	0.4874 (2)	0.06731 (12)	0.10512 (13)	0.0112 (5)
C3D	0.4433 (3)	0.12702 (15)	0.09583 (15)	0.0099 (6)
C31D	0.5044 (3)	0.17357 (14)	0.04717 (15)	0.0111 (6)
C32D	0.4295 (3)	0.23465 (15)	0.03852 (17)	0.0136 (7)
H31D	0.350 (3)	0.2213 (18)	0.0255 (18)	0.019 (6)*
H32D	0.465 (3)	0.2623 (18)	0.0071 (19)	0.019 (6)*
H33D	0.412 (3)	0.2604 (19)	0.083 (2)	0.019 (6)*
C33D	0.6267 (3)	0.19160 (16)	0.07746 (16)	0.0139 (7)
H34D	0.615 (3)	0.2122 (18)	0.1231 (19)	0.019 (5)*
H35D	0.670 (3)	0.2205 (18)	0.0483 (19)	0.019 (5)*
H36D	0.685 (3)	0.1532 (18)	0.0873 (18)	0.019 (5)*
C34D	0.5227 (3)	0.14097 (16)	−0.02294 (16)	0.0167 (7)
H37D	0.445 (3)	0.1306 (18)	−0.0436 (18)	0.017 (5)*
H38D	0.576 (3)	0.1034 (18)	−0.0177 (18)	0.017 (5)*
H39D	0.563 (3)	0.1737 (18)	−0.0532 (18)	0.017 (5)*
C4D	0.3433 (3)	0.13674 (15)	0.13743 (15)	0.0110 (6)
H4D	0.296 (3)	0.176 (2)	0.1401 (19)	0.022 (10)*
C5D	0.3275 (3)	0.07974 (15)	0.17349 (15)	0.0108 (6)
C51D	0.2368 (3)	0.06001 (14)	0.22664 (15)	0.0101 (6)
C52D	0.2597 (3)	−0.00971 (15)	0.25078 (14)	0.0140 (6)
H51D	0.347 (3)	−0.0114 (18)	0.2715 (18)	0.021 (5)*
H52D	0.250 (3)	−0.0437 (18)	0.2116 (18)	0.021 (5)*
H53D	0.194 (3)	−0.0224 (18)	0.2838 (18)	0.021 (5)*
C53D	0.2460 (3)	0.10651 (15)	0.28814 (15)	0.0143 (6)
H54D	0.323 (3)	0.1040 (17)	0.3084 (18)	0.013 (5)*
H55D	0.185 (3)	0.0932 (16)	0.3229 (17)	0.013 (5)*
H56D	0.235 (3)	0.1509 (18)	0.2748 (17)	0.013 (5)*
C54D	0.1114 (3)	0.06523 (16)	0.19576 (16)	0.0159 (6)
H57D	0.103 (3)	0.0335 (18)	0.1562 (19)	0.018 (5)*
H58D	0.091 (3)	0.1087 (19)	0.1779 (19)	0.018 (5)*
H59D	0.047 (3)	0.0537 (18)	0.2306 (18)	0.018 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0164 (13)	0.0081 (13)	0.0074 (12)	−0.0006 (11)	0.0006 (10)	0.0026 (10)
N2A	0.0139 (13)	0.0143 (13)	0.0041 (11)	−0.0035 (11)	0.0017 (10)	0.0006 (10)
C3A	0.0125 (14)	0.0105 (15)	0.0064 (14)	−0.0021 (11)	−0.0037 (11)	−0.0002 (11)
C31A	0.0169 (15)	0.0101 (15)	0.0064 (14)	−0.0013 (12)	0.0015 (12)	0.0018 (11)
C32A	0.0161 (17)	0.0129 (15)	0.0091 (14)	−0.0012 (12)	−0.0011 (12)	0.0002 (12)
C33A	0.0146 (16)	0.0127 (15)	0.0162 (16)	−0.0011 (13)	0.0035 (13)	0.0035 (12)
C34A	0.0215 (18)	0.0161 (16)	0.0059 (14)	−0.0004 (13)	0.0018 (12)	0.0007 (12)
C4A	0.0151 (15)	0.0120 (14)	0.0049 (13)	−0.0002 (12)	0.0002 (11)	−0.0001 (11)
C5A	0.0136 (14)	0.0128 (15)	0.0073 (13)	−0.0006 (12)	−0.0040 (11)	−0.0056 (11)
C51A	0.0135 (14)	0.0105 (14)	0.0099 (14)	−0.0005 (11)	0.0008 (11)	0.0016 (11)
C52A	0.0170 (15)	0.0155 (15)	0.0114 (14)	0.0014 (13)	0.0030 (13)	0.0025 (12)
C53A	0.0170 (15)	0.0148 (15)	0.0167 (15)	−0.0032 (13)	0.0048 (13)	−0.0027 (12)
C54A	0.0153 (14)	0.0187 (16)	0.0094 (14)	0.0029 (13)	0.0026 (12)	0.0037 (12)
N1B	0.0127 (13)	0.0093 (13)	0.0069 (12)	−0.0006 (10)	0.0013 (10)	0.0000 (10)
N2B	0.0124 (12)	0.0102 (13)	0.0054 (11)	−0.0029 (10)	−0.0010 (9)	−0.0006 (9)
C3B	0.0138 (15)	0.0092 (14)	0.0068 (14)	−0.0018 (11)	−0.0021 (12)	−0.0017 (11)
C31B	0.0157 (15)	0.0095 (15)	0.0102 (14)	0.0003 (11)	0.0000 (11)	0.0014 (11)
C32B	0.0173 (17)	0.0115 (15)	0.0142 (16)	0.0008 (12)	0.0006 (13)	0.0011 (12)
C33B	0.030 (2)	0.0163 (16)	0.0113 (15)	−0.0014 (14)	0.0028 (14)	0.0018 (13)
C34B	0.0143 (16)	0.0178 (16)	0.0159 (16)	0.0005 (13)	0.0001 (13)	0.0050 (13)
C4B	0.0154 (16)	0.0093 (14)	0.0102 (14)	−0.0020 (12)	−0.0013 (12)	−0.0006 (11)
C5B	0.0148 (15)	0.0128 (15)	0.0040 (13)	−0.0016 (12)	−0.0010 (11)	−0.0025 (11)
C51B	0.0170 (16)	0.0098 (14)	0.0071 (14)	0.0011 (12)	0.0016 (11)	−0.0020 (11)
C52B	0.0219 (16)	0.0131 (15)	0.0136 (14)	0.0001 (12)	0.0055 (13)	0.0000 (12)
C53B	0.0173 (16)	0.0263 (18)	0.0144 (15)	−0.0047 (14)	0.0025 (13)	0.0012 (14)
C54B	0.0193 (17)	0.0171 (16)	0.0088 (14)	−0.0034 (13)	0.0042 (13)	−0.0026 (12)
N1C	0.0133 (13)	0.0090 (13)	0.0079 (12)	0.0017 (10)	0.0006 (10)	0.0032 (10)
N2C	0.0130 (13)	0.0106 (12)	0.0062 (12)	−0.0003 (10)	−0.0016 (10)	0.0004 (10)
C3C	0.0149 (15)	0.0107 (15)	0.0059 (14)	−0.0006 (12)	−0.0012 (11)	−0.0008 (11)
C31C	0.0146 (15)	0.0092 (14)	0.0085 (14)	−0.0011 (12)	0.0021 (12)	0.0001 (11)
C32C	0.0203 (18)	0.0101 (15)	0.0126 (15)	−0.0023 (13)	0.0030 (13)	0.0041 (12)
C33C	0.0232 (17)	0.0126 (15)	0.0076 (15)	−0.0006 (13)	0.0024 (12)	−0.0007 (12)
C34C	0.0150 (16)	0.0144 (16)	0.0122 (15)	−0.0019 (12)	−0.0009 (12)	0.0015 (12)
C4C	0.0131 (15)	0.0096 (14)	0.0090 (13)	0.0009 (12)	−0.0009 (11)	−0.0004 (11)
C5C	0.0140 (15)	0.0129 (15)	0.0040 (13)	−0.0009 (12)	−0.0029 (11)	0.0007 (11)
C51C	0.0153 (14)	0.0098 (13)	0.0073 (13)	−0.0005 (12)	0.0035 (11)	0.0013 (11)
C52C	0.0192 (15)	0.0133 (14)	0.0115 (14)	−0.0002 (12)	0.0035 (13)	0.0023 (11)
C53C	0.0195 (16)	0.0179 (16)	0.0094 (14)	−0.0012 (13)	0.0023 (12)	0.0037 (12)
C54C	0.0193 (15)	0.0138 (15)	0.0140 (15)	−0.0015 (13)	0.0055 (13)	−0.0003 (12)
N1D	0.0155 (13)	0.0076 (13)	0.0066 (12)	0.0002 (10)	0.0010 (10)	0.0023 (10)
N2D	0.0147 (13)	0.0108 (12)	0.0082 (12)	−0.0011 (10)	0.0022 (10)	0.0022 (10)
C3D	0.0121 (14)	0.0106 (14)	0.0069 (14)	−0.0004 (11)	−0.0049 (11)	−0.0012 (11)
C31D	0.0155 (15)	0.0106 (14)	0.0072 (14)	−0.0013 (11)	0.0014 (11)	0.0005 (11)
C32D	0.0151 (16)	0.0133 (15)	0.0124 (15)	−0.0037 (13)	−0.0012 (12)	0.0051 (12)
C33D	0.0158 (16)	0.0144 (15)	0.0115 (15)	−0.0034 (13)	0.0030 (12)	0.0033 (12)
C34D	0.0240 (18)	0.0164 (16)	0.0096 (15)	−0.0033 (14)	0.0041 (13)	0.0005 (13)
C4D	0.0160 (14)	0.0099 (14)	0.0072 (13)	0.0021 (12)	−0.0012 (12)	−0.0025 (11)
C5D	0.0133 (14)	0.0118 (14)	0.0074 (14)	−0.0023 (12)	−0.0032 (11)	−0.0017 (11)
C51D	0.0129 (14)	0.0107 (14)	0.0067 (12)	0.0001 (11)	−0.0007 (11)	0.0013 (11)
C52D	0.0187 (16)	0.0140 (15)	0.0094 (13)	0.0001 (12)	0.0016 (12)	0.0030 (11)
C53D	0.0197 (15)	0.0132 (15)	0.0100 (14)	−0.0022 (13)	0.0033 (12)	−0.0024 (11)
C54D	0.0157 (15)	0.0201 (16)	0.0120 (14)	0.0005 (13)	0.0021 (12)	0.0016 (12)

Geometric parameters (Å, º)

N1A—N2A	1.372 (4)	N1C—N2C	1.361 (4)
N1A—C5A	1.341 (4)	N1C—C5C	1.345 (4)
N2A—C3A	1.335 (4)	N2C—C3C	1.345 (4)
C3A—C4A	1.411 (4)	C3C—C4C	1.409 (4)
C3A—C31A	1.519 (4)	C3C—C31C	1.521 (4)
C31A—C32A	1.534 (4)	C31C—C32C	1.529 (4)
C31A—C33A	1.531 (4)	C31C—C33C	1.535 (4)
C31A—C34A	1.552 (4)	C31C—C34C	1.536 (4)
C4A—C5A	1.377 (4)	C4C—C5C	1.381 (4)
C5A—C51A	1.516 (4)	C5C—C51C	1.519 (4)
C51A—C52A	1.528 (4)	C51C—C52C	1.531 (4)
C51A—C53A	1.548 (4)	C51C—C53C	1.538 (4)
C51A—C54A	1.534 (4)	C51C—C54C	1.538 (4)
N1B—N2B	1.364 (4)	N1D—N2D	1.359 (4)
N1B—C5B	1.343 (4)	N1D—C5D	1.345 (4)
N2B—C3B	1.345 (4)	N2D—C3D	1.341 (4)
C3B—C4B	1.403 (4)	C3D—C4D	1.405 (4)
C3B—C31B	1.518 (4)	C3D—C31D	1.517 (4)
C31B—C32B	1.535 (4)	C31D—C32D	1.527 (4)
C31B—C33B	1.541 (4)	C31D—C33D	1.546 (4)
C31B—C34B	1.536 (4)	C31D—C34D	1.540 (4)
C4B—C5B	1.391 (4)	C4D—C5D	1.383 (4)
C5B—C51B	1.518 (4)	C5D—C51D	1.514 (4)
C51B—C52B	1.528 (4)	C51D—C52D	1.536 (4)
C51B—C53B	1.533 (4)	C51D—C53D	1.542 (4)
C51B—C54B	1.535 (4)	C51D—C54D	1.541 (4)
C5A—N1A—N2A	113.2 (3)	C5C—N1C—N2C	113.2 (3)
C3A—N2A—N1A	104.3 (2)	C3C—N2C—N1C	104.5 (2)
N2A—C3A—C4A	110.5 (3)	N2C—C3C—C4C	110.4 (3)
N2A—C3A—C31A	120.0 (3)	N2C—C3C—C31C	120.0 (3)
C4A—C3A—C31A	129.5 (3)	C4C—C3C—C31C	129.5 (3)
C3A—C31A—C32A	110.3 (2)	C3C—C31C—C32C	109.9 (2)
C3A—C31A—C33A	109.8 (2)	C3C—C31C—C33C	109.7 (2)
C3A—C31A—C34A	109.5 (2)	C3C—C31C—C34C	109.2 (2)
C32A—C31A—C33A	109.4 (3)	C32C—C31C—C33C	109.7 (3)
C32A—C31A—C34A	109.0 (2)	C32C—C31C—C34C	109.0 (3)
C33A—C31A—C34A	108.8 (3)	C33C—C31C—C34C	109.3 (3)
C3A—C4A—C5A	106.2 (3)	C3C—C4C—C5C	106.0 (3)
N1A—C5A—C4A	105.8 (3)	N1C—C5C—C4C	106.0 (3)
N1A—C5A—C51A	121.6 (3)	N1C—C5C—C51C	121.7 (3)
C4A—C5A—C51A	132.6 (3)	C4C—C5C—C51C	132.3 (3)
C5A—C51A—C52A	109.6 (2)	C5C—C51C—C52C	109.3 (2)
C5A—C51A—C53A	109.8 (2)	C5C—C51C—C53C	109.0 (2)
C5A—C51A—C54A	109.7 (2)	C5C—C51C—C54C	110.1 (2)
C52A—C51A—C53A	109.3 (2)	C52C—C51C—C53C	109.0 (2)
C52A—C51A—C54A	109.6 (2)	C52C—C51C—C54C	109.5 (2)
C53A—C51A—C54A	108.8 (2)	C53C—C51C—C54C	109.9 (2)
C5B—N1B—N2B	113.0 (3)	C5D—N1D—N2D	113.3 (3)
C3B—N2B—N1B	104.7 (2)	C3D—N2D—N1D	104.5 (2)
N2B—C3B—C4B	110.5 (3)	N2D—C3D—C4D	110.5 (3)
N2B—C3B—C31B	119.5 (3)	N2D—C3D—C31D	119.9 (3)
C4B—C3B—C31B	129.9 (3)	C4D—C3D—C31D	129.6 (3)
C3B—C31B—C32B	109.6 (3)	C3D—C31D—C32D	109.9 (3)
C3B—C31B—C33B	109.4 (2)	C3D—C31D—C33D	108.5 (2)
C3B—C31B—C34B	109.7 (2)	C3D—C31D—C34D	110.0 (3)
C32B—C31B—C33B	109.2 (3)	C32D—C31D—C33D	109.7 (3)
C32B—C31B—C34B	109.8 (3)	C32D—C31D—C34D	109.6 (3)
C33B—C31B—C34B	109.1 (3)	C33D—C31D—C34D	109.0 (3)
C3B—C4B—C5B	105.9 (3)	C3D—C4D—C5D	106.1 (3)
N1B—C5B—C4B	105.9 (3)	N1D—C5D—C4D	105.6 (3)
N1B—C5B—C51B	122.5 (3)	N1D—C5D—C51D	122.7 (3)
C4B—C5B—C51B	131.6 (3)	C4D—C5D—C51D	131.7 (3)
C5B—C51B—C52B	110.4 (2)	C5D—C51D—C52D	110.4 (2)
C5B—C51B—C53B	109.3 (2)	C5D—C51D—C53D	108.8 (2)
C5B—C51B—C54B	109.1 (2)	C5D—C51D—C54D	109.4 (2)
C52B—C51B—C53B	109.4 (3)	C52D—C51D—C53D	109.4 (2)
C52B—C51B—C54B	109.6 (2)	C52D—C51D—C54D	109.9 (2)
C53B—C51B—C54B	108.9 (3)	C53D—C51D—C54D	108.9 (2)
C5A—N1A—N2A—C3A	0.2 (3)	C5C—N1C—N2C—C3C	0.0 (3)
N1A—N2A—C3A—C31A	−180.0 (3)	N1C—N2C—C3C—C31C	−177.6 (2)
N1A—N2A—C3A—C4A	−0.4 (3)	N1C—N2C—C3C—C4C	−0.1 (3)
N2A—C3A—C31A—C32A	−177.9 (3)	N2C—C3C—C31C—C32C	−174.4 (3)
N2A—C3A—C31A—C33A	−57.3 (4)	N2C—C3C—C31C—C33C	−53.7 (4)
N2A—C3A—C31A—C34A	62.1 (4)	N2C—C3C—C31C—C34C	66.1 (3)
C4A—C3A—C31A—C32A	2.5 (4)	C4C—C3C—C31C—C32C	8.6 (4)
C4A—C3A—C31A—C33A	123.1 (3)	C4C—C3C—C31C—C33C	129.4 (3)
C4A—C3A—C31A—C34A	−117.4 (3)	C4C—C3C—C31C—C34C	−110.9 (3)
N2A—C3A—C4A—C5A	0.4 (3)	N2C—C3C—C4C—C5C	0.2 (3)
C31A—C3A—C4A—C5A	180.0 (3)	C31C—C3C—C4C—C5C	177.4 (3)
N2A—N1A—C5A—C4A	0.0 (3)	N2C—N1C—C5C—C4C	0.1 (3)
N2A—N1A—C5A—C51A	−179.3 (2)	N2C—N1C—C5C—C51C	177.7 (2)
C3A—C4A—C5A—N1A	−0.2 (3)	C3C—C4C—C5C—N1C	−0.2 (3)
C3A—C4A—C5A—C51A	179.0 (3)	C3C—C4C—C5C—C51C	−177.4 (3)
N1A—C5A—C51A—C52A	179.6 (3)	N1C—C5C—C51C—C52C	171.5 (3)
N1A—C5A—C51A—C53A	−60.3 (4)	N1C—C5C—C51C—C53C	−69.5 (3)
N1A—C5A—C51A—C54A	59.2 (3)	N1C—C5C—C51C—C54C	51.2 (4)
C4A—C5A—C51A—C52A	0.4 (4)	C4C—C5C—C51C—C52C	−11.7 (4)
C4A—C5A—C51A—C53A	120.6 (4)	C4C—C5C—C51C—C53C	107.3 (4)
C4A—C5A—C51A—C54A	−120.0 (3)	C4C—C5C—C51C—C54C	−132.0 (3)
C5B—N1B—N2B—C3B	−0.5 (3)	C5D—N1D—N2D—C3D	0.0 (3)
N1B—N2B—C3B—C31B	180.0 (2)	N1D—N2D—C3D—C31D	178.0 (2)
N1B—N2B—C3B—C4B	0.0 (3)	N1D—N2D—C3D—C4D	−0.1 (3)
N2B—C3B—C31B—C32B	−178.4 (3)	N2D—C3D—C31D—C32D	172.9 (3)
N2B—C3B—C31B—C33B	−58.8 (4)	N2D—C3D—C31D—C33D	−67.1 (3)
N2B—C3B—C31B—C34B	60.9 (4)	N2D—C3D—C31D—C34D	52.1 (4)
C4B—C3B—C31B—C32B	1.5 (4)	C4D—C3D—C31D—C32D	−9.3 (4)
C4B—C3B—C31B—C33B	121.2 (3)	C4D—C3D—C31D—C33D	110.7 (3)
C4B—C3B—C31B—C34B	−119.1 (3)	C4D—C3D—C31D—C34D	−130.2 (3)
N2B—C3B—C4B—C5B	0.5 (3)	N2D—C3D—C4D—C5D	0.2 (3)
C31B—C3B—C4B—C5B	−179.5 (3)	C31D—C3D—C4D—C5D	−177.8 (3)
N2B—N1B—C5B—C4B	0.8 (3)	N2D—N1D—C5D—C4D	0.1 (3)
N2B—N1B—C5B—C51B	−178.9 (3)	N2D—N1D—C5D—C51D	−179.4 (3)
C3B—C4B—C5B—N1B	−0.7 (3)	C3D—C4D—C5D—N1D	−0.1 (3)
C3B—C4B—C5B—C51B	178.9 (3)	C3D—C4D—C5D—C51D	179.3 (3)
N1B—C5B—C51B—C52B	6.7 (4)	N1D—C5D—C51D—C52D	−0.6 (4)
N1B—C5B—C51B—C53B	127.1 (3)	N1D—C5D—C51D—C53D	119.5 (3)
N1B—C5B—C51B—C54B	−113.9 (3)	N1D—C5D—C51D—C54D	−121.7 (3)
C4B—C5B—C51B—C52B	−173.0 (3)	C4D—C5D—C51D—C52D	−179.9 (3)
C4B—C5B—C51B—C53B	−52.6 (4)	C4D—C5D—C51D—C53D	−59.8 (4)
C4B—C5B—C51B—C54B	66.5 (4)	C4D—C5D—C51D—C54D	59.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N2B	0.83 (4)	2.10 (4)	2.862 (4)	152 (3)
N1B—H1B···N2A	0.91 (4)	2.05 (4)	2.865 (4)	149 (3)
N1C—H1C···N2D	0.86 (5)	2.06 (5)	2.845 (4)	152 (4)
N1D—H1D···N2C	0.86 (5)	2.09 (5)	2.866 (4)	149 (4)

(100k)

Crystal data

C11H20N2	F(000) = 1600
Mr = 180.29	Dx = 1.035 Mg m^−3
Orthorhombic, Pb21a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2a -2ab	Cell parameters from 14 reflections
a = 11.366 (2) Å	θ = 16.0–16.6°
b = 20.654 (5) Å	µ = 0.06 mm^−1
c = 19.723 (4) Å	T = 100 K
V = 4630.0 (17) Å^3	Prism, colourless
Z = 16	0.44 × 0.34 × 0.20 mm

Data collection

Huber 512 goniometer diffractometer	3456 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
None monochromator	θmax = 25.1°, θmin = 2.0°
ω–2θ scan	h = 0→13
Absorption correction: gaussian Xtal 3.7 (Hall, du Boulay & Olthof-Hazekamp, 2000)	k = 0→24
Tmin = 0.980, Tmax = 0.988	l = 0→23
4203 measured reflections	3 standard reflections every 100 reflections
4203 independent reflections	intensity decay: 2%

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)] = 0.079	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.226	w = 1/[σ^2(Fo^2) + (0.1043P)^2 + 4.3675P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.003
4203 reflections	Δρmax = 0.45 e Å^−3
524 parameters	Δρmin = −0.31 e Å^−3
1 restraint	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −1 (6)

Special details

Experimental. The correction for the absorption by the beryllium shield was performed by PROFIT (Streltsov & Zavodnik, 1989) program.

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
N1A	0.3969 (4)	0.0545 (3)	0.6486 (2)	0.0178 (11)
H1A	0.4074	0.0152	0.6648	0.021*
N2A	0.4718 (4)	0.0823 (3)	0.6029 (3)	0.0187 (11)
C3A	0.4253 (6)	0.1406 (3)	0.5917 (3)	0.0208 (14)
C31A	0.4864 (6)	0.1877 (3)	0.5423 (3)	0.0263 (15)
C32A	0.4178 (6)	0.2504 (3)	0.5399 (4)	0.0289 (16)
H31A	0.414 (3)	0.2699 (15)	0.587 (2)	0.043*
H32A	0.335 (4)	0.2415 (6)	0.523 (2)	0.043*
H33A	0.458 (3)	0.2816 (15)	0.508 (2)	0.043*
C33A	0.6123 (6)	0.2005 (4)	0.5666 (4)	0.0376 (19)
H34A	0.6105 (7)	0.216 (3)	0.612 (2)	0.056*
H35A	0.648 (2)	0.232 (2)	0.538 (2)	0.056*
H36A	0.656 (3)	0.1612 (19)	0.565 (3)	0.056*
C34A	0.4860 (8)	0.1565 (4)	0.4705 (4)	0.042 (2)
H37A	0.401 (4)	0.151 (2)	0.4541 (14)	0.063*
H38A	0.525 (5)	0.112 (2)	0.4726 (6)	0.063*
H39A	0.531 (5)	0.1855 (18)	0.4377 (16)	0.063*
C4A	0.3195 (5)	0.1487 (3)	0.6307 (3)	0.0195 (13)
H4A	0.2694	0.1855	0.6316	0.023*
C5A	0.3061 (5)	0.0920 (3)	0.6665 (3)	0.0207 (13)
C51A	0.2132 (5)	0.0706 (3)	0.7178 (3)	0.0243 (14)
C52A	0.1228 (6)	0.1246 (4)	0.7271 (4)	0.0384 (17)
H51A	0.166 (2)	0.167 (2)	0.743 (2)	0.058*
H52A	0.060 (4)	0.1106 (12)	0.764 (2)	0.058*
H53A	0.080 (3)	0.1334 (17)	0.680 (2)	0.058*
C53A	0.1514 (8)	0.0096 (4)	0.6928 (4)	0.051 (2)
H54A	0.108 (4)	0.0195 (9)	0.648 (3)	0.076*
H55A	0.092 (4)	−0.0057 (17)	0.729 (2)	0.076*
H56A	0.213 (3)	−0.0263 (19)	0.685 (3)	0.076*
C54A	0.2723 (6)	0.0580 (4)	0.7867 (3)	0.0423 (19)
H57A	0.318 (4)	0.0969 (19)	0.8005 (15)	0.063*
H58A	0.326 (4)	0.020 (2)	0.7829 (8)	0.063*
H59A	0.211 (3)	0.049 (3)	0.8213 (16)	0.063*
N1B	0.5908 (4)	−0.0402 (3)	0.6005 (2)	0.0182 (11)
H1B	0.5806	−0.0013	0.5833	0.022*
N2B	0.5165 (5)	−0.0671 (3)	0.6482 (3)	0.0207 (12)
C3B	0.5638 (6)	−0.1256 (3)	0.6591 (3)	0.0219 (15)
C31B	0.5052 (6)	−0.1708 (3)	0.7091 (3)	0.0245 (15)
C32B	0.5785 (7)	−0.2330 (4)	0.7174 (4)	0.0314 (17)
H31B	0.581 (7)	−0.262 (4)	0.673 (4)	0.047*
H32B	0.542 (7)	−0.267 (4)	0.755 (4)	0.047*
H33B	0.654 (7)	−0.216 (4)	0.737 (4)	0.047*
C33B	0.4958 (10)	−0.1383 (4)	0.7792 (4)	0.055 (3)
H34B	0.446 (5)	−0.103 (3)	0.7765 (9)	0.083*
H35B	0.569 (4)	−0.125 (3)	0.7930 (18)	0.083*
H36B	0.466 (6)	−0.1676 (19)	0.8102 (19)	0.083*
C34B	0.3812 (6)	−0.1883 (4)	0.6843 (4)	0.039 (2)
H37B	0.3869 (7)	−0.212 (3)	0.639 (3)	0.059*
H38B	0.333 (3)	−0.147 (2)	0.679 (3)	0.059*
H39B	0.342 (3)	−0.217 (3)	0.719 (2)	0.059*
C4B	0.6641 (5)	−0.1346 (3)	0.6203 (3)	0.0223 (14)
H4B	0.7128	−0.1720	0.6197	0.027*
C5B	0.6798 (5)	−0.0792 (3)	0.5830 (3)	0.0208 (14)
C51B	0.7749 (6)	−0.0589 (3)	0.5323 (3)	0.0267 (15)
C52B	0.7567 (8)	0.0120 (4)	0.5118 (4)	0.053 (2)
H51B	0.768 (5)	0.0433 (14)	0.5568 (19)	0.079*
H52B	0.667 (4)	0.0182 (7)	0.491 (3)	0.079*
H53B	0.822 (4)	0.0255 (10)	0.473 (3)	0.079*
C53B	0.8953 (7)	−0.0653 (6)	0.5644 (4)	0.067 (3)
H54B	0.905 (2)	−0.028 (3)	0.605 (3)	0.100*
H55B	0.964 (4)	−0.058 (3)	0.525 (2)	0.100*
H56B	0.905 (2)	−0.114 (3)	0.587 (3)	0.100*
C54B	0.7656 (7)	−0.0997 (4)	0.4685 (3)	0.0443 (19)
H57B	0.673 (4)	−0.096 (2)	0.4472 (17)	0.066*
H58B	0.786 (4)	−0.152 (2)	0.4813 (7)	0.066*
H59B	0.831 (4)	−0.0816 (18)	0.4294 (18)	0.066*
N1C	0.5989 (5)	−0.0544 (3)	0.0996 (3)	0.0214 (12)
H1C	0.5909	−0.0140	0.0860	0.026*
N2C	0.5278 (4)	−0.0829 (3)	0.1474 (3)	0.0203 (12)
C3C	0.5694 (5)	−0.1429 (3)	0.1530 (3)	0.0168 (13)
C31C	0.5094 (5)	−0.1899 (3)	0.2007 (3)	0.0172 (13)
C32C	0.5805 (6)	−0.2542 (3)	0.2043 (4)	0.0289 (16)
H31C	0.667 (4)	−0.2443 (5)	0.220 (2)	0.043*
H32C	0.582 (3)	−0.2761 (14)	0.1563 (19)	0.043*
H33C	0.541 (3)	−0.2856 (15)	0.239 (2)	0.043*
C33C	0.5003 (8)	−0.1604 (4)	0.2726 (3)	0.0360 (18)
H34C	0.577 (4)	−0.148 (2)	0.2879 (13)	0.054*
H35C	0.468 (5)	−0.1921 (16)	0.3032 (15)	0.054*
H36C	0.450 (4)	−0.123 (2)	0.2714 (6)	0.054*
C34C	0.3852 (6)	−0.2055 (4)	0.1743 (4)	0.0320 (17)
H37C	0.3913 (7)	−0.227 (2)	0.126 (2)	0.048*
H38C	0.336 (2)	−0.1626 (18)	0.171 (2)	0.048*
H39C	0.344 (2)	−0.238 (2)	0.2078 (19)	0.048*
C4C	0.6652 (5)	−0.1529 (3)	0.1098 (3)	0.0208 (13)
H4C	0.7095	−0.1917	0.1048	0.025*
C5C	0.6825 (5)	−0.0951 (3)	0.0757 (3)	0.0193 (13)
C51C	0.7683 (6)	−0.0750 (3)	0.0210 (3)	0.0241 (14)
C52C	0.8636 (7)	−0.1274 (4)	0.0121 (4)	0.0429 (18)
H51C	0.907 (3)	−0.1359 (18)	0.060 (2)	0.064*
H52C	0.928 (4)	−0.1112 (13)	−0.025 (2)	0.064*
H53C	0.8229 (18)	−0.1722 (19)	−0.005 (3)	0.064*
C53C	0.7033 (7)	−0.0673 (4)	−0.0458 (3)	0.0449 (19)
H54C	0.635 (4)	−0.031 (2)	−0.0403 (9)	0.067*
H55C	0.664 (4)	−0.113 (2)	−0.0599 (15)	0.067*
H56C	0.764 (3)	−0.052 (3)	−0.0845 (17)	0.067*
C54C	0.8289 (8)	−0.0118 (4)	0.0404 (4)	0.060 (3)
H57C	0.870 (5)	−0.0173 (10)	0.087 (3)	0.090*
H58C	0.767 (3)	0.025 (2)	0.044 (3)	0.090*
H59C	0.891 (5)	0.0000 (17)	0.004 (2)	0.090*
N1D	0.4137 (4)	0.0409 (3)	0.1519 (2)	0.0179 (12)
H1D	0.4238	0.0012	0.1671	0.022*
N2D	0.4844 (4)	0.0685 (3)	0.1048 (3)	0.0196 (12)
C3D	0.4414 (5)	0.1278 (3)	0.0945 (3)	0.0194 (14)
C31D	0.5027 (6)	0.1735 (3)	0.0468 (3)	0.0247 (15)
C32D	0.4282 (6)	0.2350 (4)	0.0389 (4)	0.0334 (18)
H31D	0.348 (4)	0.2232 (6)	0.022 (2)	0.050*
H32D	0.466 (3)	0.2646 (16)	0.006 (2)	0.050*
H33D	0.422 (4)	0.2573 (16)	0.0835 (19)	0.050*
C33D	0.6235 (6)	0.1919 (4)	0.0765 (4)	0.0326 (17)
H34D	0.6130 (8)	0.210 (2)	0.121 (2)	0.049*
H35D	0.661 (3)	0.223 (2)	0.0472 (19)	0.049*
H36D	0.672 (3)	0.1534 (18)	0.080 (2)	0.049*
C34D	0.5182 (9)	0.1415 (4)	−0.0230 (4)	0.052 (2)
H37D	0.440 (4)	0.131 (3)	−0.0419 (17)	0.077*
H38D	0.565 (5)	0.101 (3)	−0.0180 (6)	0.077*
H39D	0.559 (5)	0.1717 (19)	−0.0539 (18)	0.077*
C4D	0.3406 (6)	0.1374 (3)	0.1378 (3)	0.0214 (13)
H4D	0.2937	0.1754	0.1412	0.026*
C5D	0.3259 (5)	0.0800 (3)	0.1735 (3)	0.0217 (14)
C51D	0.2342 (5)	0.0599 (3)	0.2254 (3)	0.0198 (13)
C52D	0.2578 (6)	−0.0080 (3)	0.2499 (3)	0.0333 (15)
H51D	0.338 (4)	−0.0095 (6)	0.274 (2)	0.050*
H52D	0.259 (4)	−0.0389 (13)	0.2094 (15)	0.050*
H53D	0.193 (3)	−0.0217 (10)	0.283 (2)	0.050*
C53D	0.2461 (7)	0.1059 (4)	0.2874 (3)	0.0392 (17)
H54D	0.324 (4)	0.0982 (18)	0.3105 (18)	0.059*
H55D	0.180 (4)	0.0971 (18)	0.3206 (19)	0.059*
H56D	0.242 (5)	0.1525 (19)	0.2715 (7)	0.059*
C54D	0.1110 (5)	0.0658 (4)	0.1950 (4)	0.0399 (18)
H57D	0.1053 (15)	0.038 (2)	0.153 (2)	0.060*
H58D	0.0953 (19)	0.113 (2)	0.182 (2)	0.060*
H59D	0.050 (3)	0.051 (2)	0.2298 (17)	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.021 (3)	0.019 (3)	0.013 (2)	−0.001 (2)	0.001 (2)	0.001 (2)
N2A	0.021 (2)	0.019 (3)	0.017 (2)	0.001 (2)	0.002 (2)	0.000 (2)
C3A	0.023 (3)	0.023 (3)	0.016 (3)	−0.003 (3)	0.004 (2)	0.006 (2)
C31A	0.026 (3)	0.029 (4)	0.023 (3)	−0.004 (3)	0.007 (3)	0.009 (3)
C32A	0.023 (3)	0.029 (4)	0.035 (4)	−0.007 (3)	−0.002 (3)	0.009 (3)
C33A	0.020 (3)	0.044 (5)	0.049 (5)	−0.006 (3)	0.002 (3)	0.012 (4)
C34A	0.064 (5)	0.039 (4)	0.023 (3)	−0.002 (4)	0.006 (4)	0.007 (3)
C4A	0.018 (3)	0.026 (3)	0.015 (3)	0.003 (3)	0.000 (2)	−0.002 (2)
C5A	0.020 (3)	0.023 (3)	0.020 (3)	0.001 (3)	−0.003 (2)	−0.004 (3)
C51A	0.015 (3)	0.032 (3)	0.026 (3)	−0.007 (3)	−0.002 (2)	0.004 (3)
C52A	0.032 (4)	0.043 (4)	0.040 (4)	0.010 (3)	0.021 (3)	0.013 (3)
C53A	0.053 (5)	0.045 (5)	0.054 (5)	−0.020 (4)	0.015 (4)	−0.005 (4)
C54A	0.032 (4)	0.068 (5)	0.027 (3)	0.005 (4)	0.008 (3)	0.020 (4)
N1B	0.018 (3)	0.020 (3)	0.017 (2)	0.002 (2)	−0.004 (2)	0.004 (2)
N2B	0.021 (3)	0.022 (3)	0.019 (3)	−0.002 (2)	0.004 (2)	0.002 (2)
C3B	0.020 (3)	0.024 (4)	0.022 (3)	−0.008 (3)	−0.002 (3)	−0.001 (3)
C31B	0.030 (3)	0.025 (3)	0.019 (3)	−0.005 (3)	0.000 (3)	0.005 (3)
C32B	0.032 (4)	0.026 (4)	0.035 (4)	−0.001 (3)	0.002 (3)	0.011 (3)
C33B	0.095 (7)	0.046 (5)	0.025 (4)	−0.008 (5)	0.025 (4)	0.013 (4)
C34B	0.026 (4)	0.036 (4)	0.056 (5)	0.000 (3)	−0.001 (4)	0.023 (4)
C4B	0.020 (3)	0.020 (3)	0.027 (3)	0.004 (3)	0.007 (3)	−0.004 (3)
C5B	0.021 (3)	0.027 (3)	0.014 (3)	−0.006 (3)	0.004 (2)	−0.005 (2)
C51B	0.036 (4)	0.026 (3)	0.018 (3)	−0.005 (3)	0.013 (3)	−0.002 (3)
C52B	0.063 (5)	0.040 (4)	0.056 (5)	−0.007 (4)	0.040 (4)	0.002 (4)
C53B	0.036 (4)	0.117 (9)	0.046 (5)	−0.014 (5)	0.009 (4)	0.011 (5)
C54B	0.053 (5)	0.052 (5)	0.029 (3)	−0.022 (4)	0.018 (3)	−0.009 (3)
N1C	0.023 (3)	0.019 (3)	0.022 (3)	−0.002 (2)	0.003 (2)	0.002 (2)
N2C	0.016 (2)	0.028 (3)	0.016 (3)	−0.006 (2)	0.000 (2)	0.006 (2)
C3C	0.017 (3)	0.019 (3)	0.014 (3)	0.002 (2)	−0.005 (2)	−0.008 (2)
C31C	0.020 (3)	0.019 (3)	0.013 (3)	0.001 (2)	−0.001 (2)	−0.001 (2)
C32C	0.029 (3)	0.022 (3)	0.036 (4)	0.001 (3)	0.004 (3)	0.008 (3)
C33C	0.060 (5)	0.030 (4)	0.018 (3)	−0.005 (3)	0.011 (3)	−0.004 (3)
C34C	0.022 (3)	0.029 (4)	0.045 (4)	−0.003 (3)	−0.001 (3)	0.011 (3)
C4C	0.023 (3)	0.017 (3)	0.022 (3)	−0.002 (3)	−0.003 (3)	−0.002 (2)
C5C	0.016 (3)	0.025 (3)	0.017 (3)	−0.003 (3)	0.003 (2)	0.002 (2)
C51C	0.025 (3)	0.021 (3)	0.026 (3)	−0.003 (3)	0.009 (3)	0.001 (3)
C52C	0.041 (4)	0.044 (4)	0.044 (4)	0.000 (3)	0.017 (3)	0.003 (3)
C53C	0.042 (4)	0.059 (5)	0.034 (4)	−0.006 (4)	0.012 (3)	0.011 (4)
C54C	0.074 (6)	0.044 (5)	0.063 (5)	−0.025 (4)	0.056 (5)	−0.013 (4)
N1D	0.019 (3)	0.019 (3)	0.015 (2)	−0.006 (2)	0.004 (2)	0.002 (2)
N2D	0.018 (2)	0.022 (3)	0.018 (2)	0.000 (2)	0.003 (2)	0.001 (2)
C3D	0.021 (3)	0.020 (3)	0.017 (3)	−0.002 (3)	−0.003 (2)	0.002 (2)
C31D	0.022 (3)	0.023 (3)	0.029 (3)	−0.002 (3)	0.005 (3)	0.005 (3)
C32D	0.027 (4)	0.028 (4)	0.045 (4)	−0.005 (3)	−0.011 (3)	0.012 (3)
C33D	0.022 (3)	0.035 (4)	0.041 (4)	−0.012 (3)	0.001 (3)	0.013 (3)
C34D	0.082 (7)	0.039 (5)	0.033 (4)	−0.021 (5)	0.012 (4)	0.002 (4)
C4D	0.030 (3)	0.022 (3)	0.013 (3)	0.000 (3)	0.000 (3)	−0.002 (2)
C5D	0.022 (3)	0.025 (3)	0.017 (3)	0.002 (3)	−0.006 (3)	−0.005 (3)
C51D	0.016 (3)	0.024 (3)	0.020 (3)	0.004 (3)	−0.003 (2)	0.002 (2)
C52D	0.042 (4)	0.033 (4)	0.025 (3)	0.004 (3)	0.011 (3)	0.010 (3)
C53D	0.046 (4)	0.034 (4)	0.038 (4)	−0.011 (3)	0.021 (3)	−0.011 (3)
C54D	0.018 (3)	0.062 (5)	0.040 (4)	0.002 (3)	0.006 (3)	0.020 (4)

Geometric parameters (Å, º)

N1A—N2A	1.368 (7)	N1C—N2C	1.374 (7)
N1A—C5A	1.338 (8)	N1C—C5C	1.352 (8)
N2A—C3A	1.333 (9)	N2C—C3C	1.331 (8)
C3A—C4A	1.437 (8)	C3C—C4C	1.399 (8)
C3A—C31A	1.542 (9)	C3C—C31C	1.515 (9)
C31A—C32A	1.512 (10)	C31C—C32C	1.556 (9)
C31A—C33A	1.531 (10)	C31C—C33C	1.546 (8)
C31A—C34A	1.557 (9)	C31C—C34C	1.539 (9)
C4A—C5A	1.376 (9)	C4C—C5C	1.385 (9)
C5A—C51A	1.528 (8)	C5C—C51C	1.513 (8)
C51A—C52A	1.528 (9)	C51C—C52C	1.542 (10)
C51A—C53A	1.525 (10)	C51C—C53C	1.518 (9)
C51A—C54A	1.538 (9)	C51C—C54C	1.525 (10)
N1B—N2B	1.382 (7)	N1D—N2D	1.354 (7)
N1B—C5B	1.338 (8)	N1D—C5D	1.353 (8)
N2B—C3B	1.340 (9)	N2D—C3D	1.334 (9)
C3B—C4B	1.385 (9)	C3D—C4D	1.443 (9)
C3B—C31B	1.512 (9)	C3D—C31D	1.505 (9)
C31B—C32B	1.541 (10)	C31D—C32D	1.534 (10)
C31B—C33B	1.541 (10)	C31D—C33D	1.540 (9)
C31B—C34B	1.535 (10)	C31D—C34D	1.537 (10)
C4B—C5B	1.373 (9)	C4D—C5D	1.389 (9)
C5B—C51B	1.531 (8)	C5D—C51D	1.520 (9)
C51B—C52B	1.532 (10)	C51D—C52D	1.508 (9)
C51B—C53B	1.514 (11)	C51D—C53D	1.554 (9)
C51B—C54B	1.518 (9)	C51D—C54D	1.528 (8)
C5A—N1A—N2A	114.2 (5)	C5C—N1C—N2C	112.7 (5)
C3A—N2A—N1A	104.0 (5)	C3C—N2C—N1C	104.3 (5)
N2A—C3A—C4A	110.4 (5)	N2C—C3C—C4C	111.4 (6)
N2A—C3A—C31A	119.7 (6)	N2C—C3C—C31C	119.2 (5)
C4A—C3A—C31A	129.9 (6)	C4C—C3C—C31C	129.3 (6)
C3A—C31A—C32A	109.1 (5)	C3C—C31C—C32C	110.0 (5)
C3A—C31A—C33A	109.4 (6)	C3C—C31C—C33C	110.4 (5)
C3A—C31A—C34A	108.3 (6)	C3C—C31C—C34C	109.6 (5)
C32A—C31A—C33A	110.1 (6)	C32C—C31C—C33C	109.2 (5)
C32A—C31A—C34A	108.9 (6)	C32C—C31C—C34C	108.3 (5)
C33A—C31A—C34A	111.0 (6)	C33C—C31C—C34C	109.3 (6)
C3A—C4A—C5A	105.6 (6)	C3C—C4C—C5C	106.1 (6)
N1A—C5A—C4A	105.8 (6)	N1C—C5C—C4C	105.6 (5)
N1A—C5A—C51A	122.7 (6)	N1C—C5C—C51C	122.1 (6)
C4A—C5A—C51A	131.5 (6)	C4C—C5C—C51C	132.3 (6)
C5A—C51A—C52A	109.4 (5)	C5C—C51C—C52C	110.0 (5)
C5A—C51A—C53A	110.1 (6)	C5C—C51C—C53C	109.5 (5)
C5A—C51A—C54A	109.4 (5)	C5C—C51C—C54C	110.3 (5)
C52A—C51A—C53A	109.4 (6)	C52C—C51C—C53C	108.5 (6)
C52A—C51A—C54A	108.1 (6)	C52C—C51C—C54C	108.2 (6)
C53A—C51A—C54A	110.4 (6)	C53C—C51C—C54C	110.4 (7)
C5B—N1B—N2B	113.3 (5)	C5D—N1D—N2D	113.7 (5)
C3B—N2B—N1B	103.1 (5)	C3D—N2D—N1D	105.9 (5)
N2B—C3B—C4B	111.3 (6)	N2D—C3D—C4D	109.1 (6)
N2B—C3B—C31B	118.9 (6)	N2D—C3D—C31D	120.2 (6)
C4B—C3B—C31B	129.8 (6)	C4D—C3D—C31D	130.6 (6)
C3B—C31B—C32B	110.2 (6)	C3D—C31D—C32D	109.2 (6)
C3B—C31B—C33B	110.3 (6)	C3D—C31D—C33D	109.2 (5)
C3B—C31B—C34B	110.0 (5)	C3D—C31D—C34D	110.0 (6)
C32B—C31B—C33B	107.7 (6)	C32D—C31D—C33D	109.1 (6)
C32B—C31B—C34B	109.5 (6)	C32D—C31D—C34D	109.2 (7)
C33B—C31B—C34B	109.0 (7)	C33D—C31D—C34D	110.1 (6)
C3B—C4B—C5B	106.9 (6)	C3D—C4D—C5D	106.1 (6)
N1B—C5B—C4B	105.4 (5)	N1D—C5D—C4D	105.2 (6)
N1B—C5B—C51B	122.5 (6)	N1D—C5D—C51D	123.7 (6)
C4B—C5B—C51B	132.1 (6)	C4D—C5D—C51D	131.1 (6)
C5B—C51B—C52B	109.8 (6)	C5D—C51D—C52D	110.3 (5)
C5B—C51B—C53B	110.0 (6)	C5D—C51D—C53D	107.6 (5)
C5B—C51B—C54B	109.8 (5)	C5D—C51D—C54D	110.0 (5)
C52B—C51B—C53B	108.4 (7)	C52D—C51D—C53D	107.6 (5)
C52B—C51B—C54B	107.6 (6)	C52D—C51D—C54D	111.3 (6)
C53B—C51B—C54B	111.2 (7)	C54D—C51D—C53D	109.8 (6)
C5A—N1A—N2A—C3A	0.1 (7)	C5C—N1C—N2C—C3C	0.1 (7)
N1A—N2A—C3A—C31A	179.6 (5)	N1C—N2C—C3C—C31C	−178.4 (5)
N1A—N2A—C3A—C4A	−0.5 (6)	N1C—N2C—C3C—C4C	0.0 (6)
N2A—C3A—C31A—C32A	−178.8 (6)	N2C—C3C—C31C—C32C	−174.2 (5)
N2A—C3A—C31A—C33A	−58.3 (9)	N2C—C3C—C31C—C33C	−53.6 (7)
N2A—C3A—C31A—C34A	62.7 (8)	N2C—C3C—C31C—C34C	66.8 (7)
C4A—C3A—C31A—C32A	1.3 (10)	C4C—C3C—C31C—C32C	7.7 (9)
C4A—C3A—C31A—C33A	121.8 (8)	C4C—C3C—C31C—C33C	128.3 (7)
C4A—C3A—C31A—C34A	−117.1 (8)	C4C—C3C—C31C—C34C	−111.3 (7)
N2A—C3A—C4A—C5A	0.7 (7)	N2C—C3C—C4C—C5C	−0.1 (7)
C31A—C3A—C4A—C5A	−179.4 (7)	C31C—C3C—C4C—C5C	178.1 (6)
N2A—N1A—C5A—C4A	0.3 (7)	N2C—N1C—C5C—C4C	−0.1 (7)
N2A—N1A—C5A—C51A	−179.1 (5)	N2C—N1C—C5C—C51C	177.9 (5)
C3A—C4A—C5A—N1A	−0.6 (6)	C3C—C4C—C5C—N1C	0.1 (7)
C3A—C4A—C5A—C51A	178.7 (6)	C3C—C4C—C5C—C51C	−177.6 (6)
N1A—C5A—C51A—C52A	179.7 (6)	N1C—C5C—C51C—C52C	171.6 (6)
N1A—C5A—C51A—C53A	−60.0 (8)	N1C—C5C—C51C—C53C	−69.3 (8)
N1A—C5A—C51A—C54A	61.5 (8)	N1C—C5C—C51C—C54C	52.3 (9)
C4A—C5A—C51A—C52A	0.5 (9)	C4C—C5C—C51C—C52C	−11.0 (10)
C4A—C5A—C51A—C53A	120.9 (8)	C4C—C5C—C51C—C53C	108.1 (8)
C4A—C5A—C51A—C54A	−117.7 (8)	C4C—C5C—C51C—C54C	−130.2 (8)
C5B—N1B—N2B—C3B	−0.6 (7)	C5D—N1D—N2D—C3D	−0.4 (7)
N1B—N2B—C3B—C31B	−179.5 (5)	N1D—N2D—C3D—C31D	177.4 (5)
N1B—N2B—C3B—C4B	0.7 (7)	N1D—N2D—C3D—C4D	0.7 (7)
N2B—C3B—C31B—C32B	−176.0 (6)	N2D—C3D—C31D—C32D	174.2 (6)
N2B—C3B—C31B—C33B	−57.2 (8)	N2D—C3D—C31D—C33D	−66.6 (8)
N2B—C3B—C31B—C34B	63.1 (8)	N2D—C3D—C31D—C34D	54.3 (8)
C4B—C3B—C31B—C32B	3.7 (10)	C4D—C3D—C31D—C32D	−10.0 (10)
C4B—C3B—C31B—C33B	122.6 (8)	C4D—C3D—C31D—C33D	109.2 (8)
C4B—C3B—C31B—C34B	−117.1 (8)	C4D—C3D—C31D—C34D	−129.8 (8)
N2B—C3B—C4B—C5B	−0.5 (7)	N2D—C3D—C4D—C5D	−0.7 (7)
C31B—C3B—C4B—C5B	179.7 (6)	C31D—C3D—C4D—C5D	−176.9 (6)
N2B—N1B—C5B—C4B	0.3 (7)	N2D—N1D—C5D—C4D	0.0 (7)
N2B—N1B—C5B—C51B	−178.4 (5)	N2D—N1D—C5D—C51D	179.2 (5)
C3B—C4B—C5B—N1B	0.1 (7)	C3D—C4D—C5D—N1D	0.4 (7)
C3B—C4B—C5B—C51B	178.6 (6)	C3D—C4D—C5D—C51D	−178.7 (6)
N1B—C5B—C51B—C52B	5.0 (9)	N1D—C5D—C51D—C52D	1.5 (8)
N1B—C5B—C51B—C53B	124.1 (8)	N1D—C5D—C51D—C53D	118.7 (7)
N1B—C5B—C51B—C54B	−113.2 (7)	N1D—C5D—C51D—C54D	−121.7 (7)
C4B—C5B—C51B—C52B	−173.3 (7)	C4D—C5D—C51D—C52D	−179.5 (6)
C4B—C5B—C51B—C53B	−54.2 (10)	C4D—C5D—C51D—C53D	−62.3 (8)
C4B—C5B—C51B—C54B	68.5 (9)	C4D—C5D—C51D—C54D	57.3 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N2B	0.88	2.13	2.855 (8)	139
N1B—H1B···N2A	0.88	2.16	2.870 (8)	138
N1C—H1C···N2D	0.88	2.12	2.854 (8)	140
N1D—H1D···N2C	0.88	2.14	2.868 (8)	140

(120k)

Crystal data

C11H20N2	F(000) = 800
Mr = 180.29	Dx = 1.038 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14 reflections
a = 11.356 (2) Å	θ = 16.0–16.8°
b = 20.637 (4) Å	µ = 0.06 mm^−1
c = 9.850 (2) Å	T = 120 K
V = 2308.4 (8) Å^3	Prism, colourless
Z = 8	0.44 × 0.34 × 0.20 mm

Data collection

Huber 512 goniometer diffractometer	1419 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
None monochromator	θmax = 25.1°, θmin = 2.0°
ω–2θ scan	h = 0→13
Absorption correction: gaussian Xtal 3.7 (Hall, du Boulay & Olthof-Hazekamp, 2000)	k = 0→24
Tmin = 0.979, Tmax = 0.987	l = 0→11
2043 measured reflections	3 standard reflections every 100 reflections
2043 independent reflections	intensity decay: 2%

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)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.162	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 0.8688P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2043 reflections	Δρmax = 0.23 e Å^−3
164 parameters	Δρmin = −0.19 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: 0.0044 (18)

Special details

Experimental. The correction for the absorption by the beryllium shield was performed by PROFIT (Streltsov & Zavodnik, 1989) program.

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	Occ. (<1)
N1	0.40361 (16)	0.04686 (10)	0.45044 (18)	0.0281 (5)
H1	0.423 (2)	0.0043 (14)	0.427 (3)	0.051 (8)*
N2	0.47649 (16)	0.07557 (9)	0.54291 (18)	0.0285 (5)
C3	0.4297 (2)	0.13456 (11)	0.5618 (2)	0.0289 (6)
C31	0.4888 (2)	0.18188 (12)	0.6582 (2)	0.0339 (6)
C32	0.4166 (2)	0.24437 (13)	0.6679 (3)	0.0455 (7)
H31	0.3337 (14)	0.2337 (2)	0.6992 (18)	0.068*
H32	0.4132 (13)	0.2659 (6)	0.5754 (15)	0.068*
H33	0.4550 (11)	0.2749 (6)	0.7354 (17)	0.068*
C33	0.4977 (3)	0.15159 (15)	0.7997 (3)	0.0600 (9)
H34	0.4152 (14)	0.1400 (9)	0.8337 (11)	0.090*
H35	0.5358 (18)	0.1840 (7)	0.8649 (13)	0.090*
H36	0.5480 (18)	0.1105 (9)	0.7949 (5)	0.090*
C34	0.6125 (2)	0.19827 (13)	0.6054 (3)	0.0473 (8)
H37	0.6061 (3)	0.2182 (9)	0.5102 (17)	0.071*
H38	0.6621 (9)	0.1568 (7)	0.6009 (17)	0.071*
H39	0.6518 (9)	0.2308 (8)	0.6697 (14)	0.071*
C4	0.3292 (2)	0.14253 (11)	0.4817 (2)	0.0315 (6)
H4	0.2806	0.1799	0.4765	0.038*
C5	0.3146 (2)	0.08515 (11)	0.4114 (2)	0.0291 (6)
C51	0.2233 (2)	0.06334 (12)	0.3090 (2)	0.0345 (6)
C52	0.2482 (5)	−0.0090 (2)	0.2657 (5)	0.0561 (13)	0.67
H51	0.331 (3)	−0.0121 (4)	0.222 (3)	0.084*	0.67
H52	0.185 (2)	−0.0239 (7)	0.196 (3)	0.084*	0.67
H53	0.245 (3)	−0.0387 (9)	0.351 (2)	0.084*	0.67
C53	0.1025 (4)	0.0669 (3)	0.3730 (5)	0.0678 (16)	0.67
H54	0.0989 (11)	0.0362 (15)	0.454 (3)	0.102*	0.67
H55	0.0403 (19)	0.0536 (18)	0.303 (2)	0.102*	0.67
H56	0.0865 (15)	0.1132 (15)	0.405 (3)	0.102*	0.67
C54	0.2313 (5)	0.1043 (2)	0.1842 (4)	0.0543 (12)	0.67
H57	0.3129 (9)	0.0981 (4)	0.1396 (8)	0.081*	0.67
H58	0.2202 (8)	0.1525 (3)	0.2102 (4)	0.081*	0.67
H59	0.1661 (7)	0.0907 (3)	0.1165 (7)	0.081*	0.67
C52'	0.1272 (8)	0.1217 (3)	0.2928 (7)	0.053 (2)	0.33
H51'	0.0971 (10)	0.1322 (3)	0.3770 (11)	0.080*	0.33
H52'	0.0668 (9)	0.1082 (4)	0.2367 (6)	0.080*	0.33
H53'	0.1634 (8)	0.1576 (3)	0.2554 (5)	0.080*	0.33
C53'	0.2803 (8)	0.0602 (6)	0.1691 (9)	0.064 (3)	0.33
H54'	0.344 (6)	0.028 (3)	0.170 (2)	0.095*	0.33
H55'	0.313 (6)	0.103 (3)	0.146 (3)	0.095*	0.33
H56'	0.221 (4)	0.048 (3)	0.101 (4)	0.095*	0.33
C54'	0.1618 (10)	0.0049 (5)	0.3503 (12)	0.067 (4)	0.33
H57'	0.211 (4)	−0.026 (3)	0.361 (9)	0.100*	0.33
H58'	0.112 (7)	−0.006 (3)	0.289 (6)	0.100*	0.33
H59'	0.126 (7)	0.0118 (15)	0.425 (7)	0.100*	0.33

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0293 (10)	0.0330 (10)	0.0221 (9)	−0.0031 (9)	−0.0013 (8)	−0.0030 (9)
N2	0.0288 (10)	0.0344 (10)	0.0222 (10)	−0.0060 (8)	0.0008 (8)	−0.0031 (8)
C3	0.0301 (12)	0.0334 (12)	0.0232 (11)	−0.0066 (10)	0.0051 (10)	0.0000 (10)
C31	0.0355 (13)	0.0390 (14)	0.0271 (12)	−0.0041 (11)	−0.0015 (11)	−0.0065 (11)
C32	0.0406 (14)	0.0445 (15)	0.0516 (17)	−0.0033 (13)	0.0028 (14)	−0.0184 (13)
C33	0.095 (2)	0.0539 (18)	0.0316 (14)	−0.0121 (18)	−0.0176 (16)	−0.0065 (13)
C34	0.0352 (14)	0.0475 (16)	0.0593 (18)	−0.0076 (12)	−0.0050 (13)	−0.0175 (14)
C4	0.0325 (12)	0.0325 (12)	0.0293 (12)	0.0012 (10)	−0.0030 (11)	−0.0001 (10)
C5	0.0295 (12)	0.0368 (13)	0.0212 (11)	−0.0044 (10)	−0.0016 (10)	0.0017 (10)
C51	0.0341 (13)	0.0403 (13)	0.0292 (12)	−0.0027 (11)	−0.0077 (11)	−0.0040 (11)
C52	0.068 (3)	0.043 (2)	0.057 (3)	0.002 (2)	−0.034 (3)	−0.009 (2)
C53	0.036 (2)	0.116 (5)	0.051 (3)	−0.008 (3)	−0.005 (2)	−0.023 (3)
C54	0.070 (3)	0.055 (3)	0.038 (2)	−0.016 (3)	−0.025 (2)	0.010 (2)
C52'	0.056 (5)	0.054 (5)	0.049 (5)	0.015 (4)	−0.027 (5)	−0.021 (4)
C53'	0.054 (6)	0.099 (8)	0.037 (5)	0.007 (6)	−0.008 (4)	−0.031 (6)
C54'	0.064 (7)	0.056 (6)	0.080 (8)	−0.024 (6)	−0.045 (7)	0.008 (6)

Geometric parameters (Å, º)

N1—N2	1.366 (3)	C4—C5	1.382 (3)
N1—C5	1.339 (3)	C5—C51	1.515 (3)
N2—C3	1.341 (3)	C51—C52	1.578 (5)
C3—C4	1.398 (3)	C51—C53	1.512 (5)
C3—C31	1.518 (3)	C51—C54	1.494 (4)
C31—C32	1.531 (3)	C51—C52'	1.633 (7)
C31—C33	1.531 (3)	C51—C54'	1.451 (9)
C31—C34	1.536 (4)	C51—C53'	1.524 (9)
C5—N1—N2	113.12 (19)	C4—C5—C51	132.1 (2)
C3—N2—N1	104.27 (18)	C5—C51—C52	109.8 (2)
N2—C3—C4	110.6 (2)	C5—C51—C53	109.2 (2)
N2—C3—C31	119.7 (2)	C5—C51—C54	109.8 (2)
C4—C3—C31	129.7 (2)	C52—C51—C53	108.7 (4)
C3—C31—C32	110.1 (2)	C52—C51—C54	107.6 (3)
C3—C31—C33	109.6 (2)	C53—C51—C54	111.8 (3)
C3—C31—C34	109.5 (2)	C5—C51—C52'	107.7 (3)
C32—C31—C33	108.8 (2)	C5—C51—C53'	108.9 (4)
C32—C31—C34	109.0 (2)	C5—C51—C54'	112.9 (4)
C33—C31—C34	109.7 (2)	C52'—C51—C53'	103.1 (5)
C3—C4—C5	106.3 (2)	C52'—C51—C54'	108.6 (6)
N1—C5—C4	105.75 (19)	C53'—C51—C54'	115.0 (7)
N1—C5—C51	122.2 (2)
C5—N1—N2—C3	0.1 (2)	C3—C4—C5—C51	−179.8 (2)
N1—N2—C3—C31	−179.08 (18)	N1—C5—C51—C52	2.5 (4)
N1—N2—C3—C4	−0.2 (2)	N1—C5—C51—C53	121.6 (3)
N2—C3—C31—C32	−177.4 (2)	N1—C5—C51—C54	−115.6 (3)
N2—C3—C31—C33	−57.7 (3)	C4—C5—C51—C52	−178.0 (3)
N2—C3—C31—C34	62.7 (3)	C4—C5—C51—C53	−58.9 (4)
C4—C3—C31—C32	4.0 (3)	C4—C5—C51—C54	63.9 (4)
C4—C3—C31—C33	123.7 (3)	N1—C5—C51—C52'	177.7 (3)
C4—C3—C31—C34	−115.9 (3)	N1—C5—C51—C53'	−71.1 (6)
N2—C3—C4—C5	0.3 (3)	N1—C5—C51—C54'	57.9 (6)
C31—C3—C4—C5	179.0 (2)	C4—C5—C51—C52'	−2.8 (4)
N2—N1—C5—C4	0.1 (3)	C4—C5—C51—C53'	108.4 (6)
N2—N1—C5—C51	179.71 (19)	C4—C5—C51—C54'	−122.6 (6)
C3—C4—C5—N1	−0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.94 (3)	2.03 (3)	2.871 (3)	149 (2)

Symmetry code: (i) −x+1, −y, −z+1.

(299k)

Crystal data

C11H20N2	F(000) = 800
Mr = 180.29	Dx = 0.988 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 24 reflections
a = 11.482 (1) Å	θ = 12.8–13.8°
b = 21.130 (2) Å	µ = 0.06 mm^−1
c = 9.992 (1) Å	T = 299 K
V = 2424.2 (4) Å^3	Prism, colourless
Z = 8	0.44 × 0.34 × 0.20 mm

Data collection

Huber 512 goniometer diffractometer	1686 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
None monochromator	θmax = 30.1°, θmin = 1.9°
ω–2θ scan	h = 0→16
Absorption correction: gaussian Xtal 3.7 (Hall, du Boulay & Olthof-Hazekamp, 2000)	k = 0→29
Tmin = 0.979, Tmax = 0.988	l = 0→14
3550 measured reflections	3 standard reflections every 100 reflections
3550 independent reflections	intensity decay: 2%

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)] = 0.090	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.335	w = 1/[σ^2(Fo^2) + (0.1631P)^2 + 0.6552P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.009
3550 reflections	Δρmax = 0.20 e Å^−3
175 parameters	Δρmin = −0.21 e Å^−3
42 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: 0.034 (7)

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	Occ. (<1)
N1	0.40413 (17)	0.04652 (10)	0.44738 (19)	0.0657 (6)
H1	0.4131	0.0087	0.4173	0.079*
N2	0.47454 (18)	0.07358 (9)	0.5407 (2)	0.0662 (6)
C3	0.4324 (2)	0.13160 (11)	0.5604 (2)	0.0643 (7)
C31	0.4894 (2)	0.17681 (11)	0.6579 (3)	0.0807 (8)
C32	0.4144 (9)	0.2314 (4)	0.7006 (14)	0.230 (12)	0.50
H31	0.4569	0.2576	0.7623	0.345*	0.50
H32	0.3454	0.2157	0.7434	0.345*	0.50
H33	0.3931	0.2560	0.6236	0.345*	0.50
C33	0.5237 (13)	0.1396 (6)	0.7797 (8)	0.272 (15)	0.50
H34	0.5603	0.1672	0.8434	0.408*	0.50
H35	0.5771	0.1067	0.7545	0.408*	0.50
H36	0.4555	0.1210	0.8192	0.408*	0.50
C34	0.5975 (7)	0.2022 (5)	0.5927 (14)	0.153 (6)	0.50
H37	0.6358	0.2309	0.6528	0.230*	0.50
H38	0.5769	0.2241	0.5119	0.230*	0.50
H39	0.6490	0.1678	0.5717	0.230*	0.50
C32'	0.4218 (6)	0.2376 (2)	0.6628 (9)	0.087 (2)	0.50
H31'	0.4582	0.2662	0.7248	0.131*	0.50
H32'	0.3435	0.2291	0.6914	0.131*	0.50
H33'	0.4204	0.2565	0.5754	0.131*	0.50
C33'	0.4917 (12)	0.1483 (5)	0.7956 (6)	0.155 (6)	0.50
H34'	0.5283	0.1773	0.8566	0.233*	0.50
H35'	0.5347	0.1094	0.7937	0.233*	0.50
H36'	0.4134	0.1401	0.8247	0.233*	0.50
C34'	0.6121 (5)	0.1911 (4)	0.6157 (13)	0.156 (8)	0.50
H37'	0.6470	0.2197	0.6788	0.233*	0.50
H38'	0.6115	0.2103	0.5286	0.233*	0.50
H39'	0.6563	0.1526	0.6126	0.233*	0.50
C4	0.3355 (2)	0.14096 (12)	0.4783 (3)	0.0739 (8)
H4	0.2905	0.1775	0.4723	0.089*
C5	0.3195 (2)	0.08565 (12)	0.4080 (3)	0.0673 (7)
C51	0.2292 (2)	0.06712 (11)	0.3052 (3)	0.0795 (8)
C52	0.2505 (8)	−0.0004 (3)	0.2633 (8)	0.121 (3)	0.50
H51	0.3234	−0.0146	0.2995	0.181*	0.50
H52	0.2531	−0.0028	0.1674	0.181*	0.50
H53	0.1887	−0.0267	0.2962	0.181*	0.50
C53	0.1093 (5)	0.0730 (5)	0.3647 (9)	0.153 (4)	0.50
H54	0.0921	0.0358	0.4163	0.230*	0.50
H55	0.0531	0.0772	0.2942	0.230*	0.50
H56	0.1062	0.1096	0.4215	0.230*	0.50
C54	0.2399 (8)	0.1100 (4)	0.1857 (6)	0.141 (4)	0.50
H57	0.3046	0.0968	0.1317	0.212*	0.50
H58	0.2523	0.1527	0.2154	0.212*	0.50
H59	0.1696	0.1080	0.1338	0.212*	0.50
C52'	0.1426 (7)	0.1212 (4)	0.2903 (9)	0.123 (3)	0.50
H51'	0.1041	0.1284	0.3742	0.184*	0.50
H52'	0.0860	0.1105	0.2234	0.184*	0.50
H53'	0.1832	0.1590	0.2639	0.184*	0.50
C53'	0.2882 (7)	0.0556 (6)	0.1710 (6)	0.164 (5)	0.50
H54'	0.3440	0.0220	0.1800	0.247*	0.50
H55'	0.3271	0.0935	0.1427	0.247*	0.50
H56'	0.2306	0.0439	0.1058	0.247*	0.50
C54'	0.1638 (8)	0.0076 (4)	0.3466 (11)	0.179 (6)	0.50
H57'	0.2177	−0.0269	0.3551	0.268*	0.50
H58'	0.1066	−0.0025	0.2798	0.268*	0.50
H59'	0.1258	0.0147	0.4308	0.268*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0686 (12)	0.0646 (11)	0.0638 (11)	−0.0034 (9)	−0.0053 (10)	−0.0077 (9)
N2	0.0702 (13)	0.0647 (12)	0.0636 (12)	−0.0053 (9)	−0.0045 (10)	−0.0095 (9)
C3	0.0681 (14)	0.0640 (13)	0.0608 (13)	−0.0074 (11)	0.0005 (11)	−0.0067 (10)
C31	0.0904 (19)	0.0735 (16)	0.0781 (17)	−0.0104 (14)	−0.0090 (15)	−0.0176 (13)
C32	0.121 (11)	0.32 (2)	0.245 (19)	0.028 (11)	0.001 (10)	−0.203 (18)
C33	0.50 (4)	0.137 (12)	0.178 (14)	−0.044 (17)	−0.22 (2)	−0.012 (11)
C34	0.177 (12)	0.164 (10)	0.120 (8)	−0.105 (9)	−0.018 (8)	−0.017 (8)
C32'	0.115 (7)	0.048 (3)	0.099 (4)	−0.006 (3)	−0.005 (4)	−0.026 (3)
C33'	0.33 (2)	0.080 (6)	0.060 (4)	−0.027 (8)	−0.022 (8)	−0.015 (4)
C34'	0.051 (4)	0.170 (11)	0.246 (18)	0.001 (5)	0.002 (6)	−0.128 (11)
C4	0.0788 (17)	0.0640 (14)	0.0789 (16)	0.0036 (12)	−0.0110 (13)	−0.0052 (11)
C5	0.0692 (14)	0.0699 (14)	0.0626 (13)	−0.0010 (11)	−0.0080 (11)	−0.0011 (11)
C51	0.0769 (17)	0.0836 (17)	0.0781 (16)	−0.0017 (14)	−0.0183 (14)	−0.0054 (14)
C52	0.142 (7)	0.110 (5)	0.110 (6)	−0.040 (5)	−0.062 (5)	0.000 (5)
C53	0.072 (4)	0.266 (14)	0.121 (7)	−0.041 (7)	−0.008 (5)	−0.045 (9)
C54	0.165 (10)	0.163 (8)	0.095 (6)	−0.044 (7)	−0.067 (6)	0.050 (6)
C52'	0.098 (6)	0.150 (7)	0.120 (7)	0.015 (5)	−0.037 (5)	−0.017 (6)
C53'	0.113 (6)	0.298 (16)	0.083 (5)	0.021 (9)	−0.036 (5)	−0.073 (8)
C54'	0.172 (11)	0.164 (9)	0.200 (13)	−0.112 (9)	−0.095 (10)	0.064 (9)

Geometric parameters (Å, º)

N1—N2	1.360 (3)	C31—C34'	1.502 (3)
N1—C5	1.335 (3)	C4—C5	1.376 (3)
N2—C3	1.332 (3)	C5—C51	1.511 (4)
C3—C4	1.397 (4)	C51—C52	1.506 (5)
C3—C31	1.513 (3)	C51—C53	1.505 (5)
C31—C32	1.502 (3)	C51—C54	1.505 (5)
C31—C33	1.502 (3)	C51—C52'	1.523 (5)
C31—C34	1.502 (3)	C51—C53'	1.522 (5)
C31—C32'	1.502 (3)	C51—C54'	1.522 (5)
C31—C33'	1.502 (3)
C5—N1—N2	112.0 (2)	C3—C4—C5	106.6 (2)
C3—N2—N1	105.8 (2)	N1—C5—C4	106.2 (2)
N2—C3—C4	109.4 (2)	N1—C5—C51	122.6 (2)
N2—C3—C31	121.3 (2)	C4—C5—C51	131.2 (2)
C4—C3—C31	129.3 (2)	C5—C51—C52	108.9 (3)
C3—C31—C32	114.9 (6)	C5—C51—C53	109.8 (4)
C3—C31—C33	107.7 (6)	C5—C51—C54	109.1 (4)
C3—C31—C34	107.7 (5)	C52—C51—C53	109.7 (2)
C32—C31—C33	108.82 (16)	C52—C51—C54	109.7 (2)
C32—C31—C34	108.82 (16)	C53—C51—C54	109.8 (2)
C33—C31—C34	108.80 (16)	C5—C51—C52'	108.7 (4)
C3—C31—C32'	109.7 (4)	C5—C51—C53'	109.6 (4)
C3—C31—C33'	110.2 (5)	C5—C51—C54'	111.6 (4)
C3—C31—C34'	110.6 (5)	C52'—C51—C53'	108.9 (2)
C32'—C31—C33'	108.77 (16)	C52'—C51—C54'	109.0 (2)
C32'—C31—C34'	108.77 (16)	C53'—C51—C54'	109.0 (2)
C33'—C31—C34'	108.79 (16)	C54—C51—C54'	138.9 (5)
C32—C31—C34'	117.6 (8)	C53—C51—C54'	60.6 (3)
C33—C31—C34'	95.0 (9)	C52—C51—C54'	51.2 (3)
C34—C31—C34'	14.1 (9)	C54—C51—C53'	50.3 (3)
C32—C31—C33'	93.3 (8)	C53—C51—C53'	140.2 (5)
C33—C31—C33'	16.9 (8)	C52—C51—C53'	62.0 (3)
C34—C31—C33'	121.8 (10)	C54—C51—C52'	61.5 (3)
C32—C31—C32'	15.6 (7)	C53—C51—C52'	51.7 (3)
C33—C31—C32'	123.9 (8)	C52—C51—C52'	142.2 (4)
C34—C31—C32'	97.8 (7)
C5—N1—N2—C3	0.1 (3)	N2—N1—C5—C4	0.2 (3)
N1—N2—C3—C31	−179.5 (2)	N2—N1—C5—C51	−179.8 (2)
N1—N2—C3—C4	−0.3 (3)	C3—C4—C5—N1	−0.4 (3)
N2—C3—C31—C32	−162.3 (6)	C3—C4—C5—C51	179.7 (3)
N2—C3—C31—C33	−40.9 (6)	N1—C5—C51—C52	1.8 (5)
N2—C3—C31—C34	76.3 (6)	N1—C5—C51—C53	121.8 (5)
C4—C3—C31—C32	18.7 (6)	N1—C5—C51—C54	−117.8 (5)
C4—C3—C31—C33	140.2 (6)	C4—C5—C51—C52	−178.3 (5)
C4—C3—C31—C34	−102.6 (6)	C4—C5—C51—C53	−58.3 (5)
N2—C3—C31—C32'	−178.3 (4)	C4—C5—C51—C54	62.1 (5)
N2—C3—C31—C33'	−58.6 (5)	N1—C5—C51—C52'	176.8 (5)
N2—C3—C31—C34'	61.7 (5)	N1—C5—C51—C53'	−64.3 (5)
C4—C3—C31—C32'	2.8 (5)	N1—C5—C51—C54'	56.6 (5)
C4—C3—C31—C33'	122.5 (5)	C4—C5—C51—C52'	−3.3 (5)
C4—C3—C31—C34'	−117.2 (5)	C4—C5—C51—C53'	115.6 (5)
N2—C3—C4—C5	0.5 (3)	C4—C5—C51—C54'	−123.5 (5)
C31—C3—C4—C5	179.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2^i	0.86	2.21	2.897 (3)	137

Symmetry code: (i) −x+1, −y, −z+1.