Growth-induced incommensurability observed in the organic co-crystal hexamethylenetetramine resorcinol

Rodriguez, S.M.B.; Palatinus, L.; Petříček, V.; Chapuis, G.

doi:10.1107/S0108768106030382

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Growth-induced incommensurability observed in the organic co-crystal hexamethylenetetramine resorcinol

S. M. B. Rodriguez, L. Palatinus, V. Petrícek and G. Chapuis

Co-crystals of hexamethylenetetramine and resorcinol were investigated by X-ray diffraction. The structure was refined in the superspace group $Xmcm(0\beta 0)s0s$ , $X = (\,{{1}\over{2}} {{1}\over{2}} 0 {{1}\over{2}}\,)$ . In the average structure the resorcinol molecules are disordered between two orientations. The main effect of the modulation in the structure is a harmonic modulation of the occupation probabilities of the two orientations of the resorcinol molecule. However, the modulated order is not perfect and the resorcinol molecules remain partially disordered. Below 270 K the crystal undergoes a phase transition to a commensurately modulated structure with modulation vector ${\bf q} = (0 {{1}\over{2}} {{1}\over{4}}\,)$ and superspace group $X2/m(0\beta \gamma)0s$ . The structure of the low-temperature phase could not be determined owing to the poor quality of the crystals affected by the reconstructive phase transition.

Keywords: organic modulated structure; occupational modulation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106030382/sn5041sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768106030382/sn5041sup2.hkl Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108768106030382/sn5041sup3.pdf No. of hydrogen bonds involving central molecule as a function of its neighborhood

Computing details top

Data collection: X-AREA (Stoe & Cie GmbH, 2005); cell refinement: X-AREA (Stoe & Cie GmbH, 2005); data reduction: X-AREA (Stoe & Cie GmbH, 2005); program(s) used to solve structure: SHELXS (Sheldrick, 1997); program(s) used to refine structure: (Jana2000; Petricek and Dusek, 2000); molecular graphics: CrystalMaker (CrystalMaker Software Ltd., 2006); software used to prepare material for publication: (Jana2000; Petricek and Dusek, 2000).

Figures top

(I) top

Crystal data top

C₁₂H₁₈N₄O₂	Z = 4
M_r = 250.3	F(000) = 536
Orthorhombic, Xmcm(0β0)s0s†	D_x = 1.251 Mg m⁻³
q = 0.37640b*	Mo Kα radiation, λ = 0.71069 Å
a = 10.3474 Å	µ = 0.09 mm⁻¹
b = 7.0763 Å	T = 298 K
c = 16.8321 Å	Block, colourless
V = 1232.5 Å³	0.4 × 0.3 × 0.2 mm

† Symmetry operations: (1) x₁, x₂, x₃, x₄; (2) −x₁, x₂, x₃, 1/2+x₄; (3) x₁, x₂, 1/2−x₃, 1/2+x₄; (4) −x₁, x₂, 1/2−x₃, x₄; (5) −x₁, −x₂, −x₃, −x₄; (6) x₁, −x₂, −x₃, 1/2−x₄; (7) −x₁, −x₂, 1/2+x₃, 1/2−x₄; (8) x₁, −x₂, 1/2+x₃, −x₄; (9) 1/2+x₁, 1/2+x₂, x₃, 1/2+x₄; (10) 1/2−x₁, 1/2+x₂, x₃, x₄; (11) 1/2+x₁, 1/2+x₂, 1/2−x₃, x₄; (12) 1/2−x₁, 1/2+x₂, 1/2−x₃, 1/2+x₄; (13) 1/2−x₁, 1/2−x₂, −x₃, 1/2−x₄; (14) 1/2+x₁, 1/2−x₂, −x₃, −x₄; (15) 1/2−x₁, 1/2−x₂, 1/2+x₃, −x₄; (16) 1/2+x₁, 1/2−x₂, 1/2+x₃, 1/2−x₄.

Data collection top

IPDS II Stoe diffractometer	R_int = 0.085
Rotation method data acquisition using ω scans	θ_max = 29.4°, θ_min = 2.4°
26753 measured reflections	h = −14→14
2462 independent reflections	k = −10→10
1098 reflections with I > 3σ(I)	l = −23→23

Refinement top

Refinement on F	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0004F²)
R[F² > 2σ(F²)] = 0.044	(Δ/σ)_max = 0.0004
wR(F²) = 0.072	Δρ_max = 0.20 e Å⁻³
S = 1.66	Δρ_min = −0.13 e Å⁻³
2462 reflections	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
86 parameters	Extinction coefficient: 4.2 (3)
H-atom parameters constrained

Crystal data top

C₁₂H₁₈N₄O₂	V = 1232.5 Å³
M_r = 250.3	Z = 4
Orthorhombic, Xmcm(0β0)s0s†	Mo Kα radiation
q = 0.37640b*	µ = 0.09 mm⁻¹
a = 10.3474 Å	T = 298 K
b = 7.0763 Å	0.4 × 0.3 × 0.2 mm
c = 16.8321 Å

Data collection top

IPDS II Stoe diffractometer	1098 reflections with I > 3σ(I)
26753 measured reflections	R_int = 0.085
2462 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	86 parameters
wR(F²) = 0.072	H-atom parameters constrained
S = 1.66	Δρ_max = 0.20 e Å⁻³
2462 reflections	Δρ_min = −0.13 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C3a	0.1047 (2)	0	0	0.0547 (6)	0.5
C4a	−0.1596 (4)	0	0	0.0625 (7)	0.5
C1a	0.0380 (3)	0.1419 (2)	0.03809 (10)	0.0493 (4)	0.5
C2a	−0.0946 (3)	0.1434 (2)	0.03839 (10)	0.0561 (5)	0.5
O1a	0.1089 (3)	0.2782 (2)	0.07462 (10)	0.0822 (4)	0.5
H13a	0.2003 (10)	0	0	0.0656*	0.5
H14a	−0.2551 (11)	0	0	0.075*	0.5
H12a	−0.1427 (2)	0.246872	0.065995	0.0673*	0.5
H10a	0.0536 (7)	0.3644 (18)	0.1058 (10)	0.0987*	0.5
N2a	0.5	0.03454 (11)	0.32215 (5)	0.0522 (3)
N1a	0.38296 (11)	0.2764 (2)	0.25	0.0719 (4)
C6a	0.5	−0.0808 (2)	0.25	0.0542 (4)
C5a	0.5	0.3908 (3)	0.25	0.0840 (7)
C7a	0.38507 (8)	0.15547 (19)	0.32013 (5)	0.0680 (3)
H16a	0.5767 (11)	−0.1607 (17)	0.25	0.065*
H15a	0.5	0.470 (2)	0.3011 (7)	0.1008*
H17a	0.305686	0.07491 (11)	0.320931	0.0816*
H27a	0.382512	0.23558 (11)	0.369042	0.0816*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C3a	0.0430 (10)	0.0659 (12)	0.0553 (10)	0	0	−0.0144 (9)
C4a	0.0448 (11)	0.0617 (12)	0.0810 (15)	0	0	0.0025 (10)
C1a	0.0514 (9)	0.0517 (7)	0.0447 (6)	−0.0014 (6)	0.0030 (5)	−0.0087 (5)
C2a	0.0533 (8)	0.0547 (8)	0.0602 (8)	0.0088 (7)	0.0098 (7)	0.0018 (6)
O1a	0.0650 (7)	0.0811 (7)	0.1007 (9)	−0.0049 (5)	0.0044 (5)	−0.0519 (7)
N2a	0.0670 (5)	0.0440 (4)	0.0457 (4)	0	0	0.0076 (3)
N1a	0.0952 (8)	0.0573 (5)	0.0630 (6)	0.0319 (5)	0	0
C6a	0.0656 (8)	0.0343 (6)	0.0627 (8)	0	0	0
C5a	0.1574 (19)	0.0343 (6)	0.0602 (9)	0	0	0
C7a	0.0779 (6)	0.0689 (5)	0.0572 (5)	0.0151 (4)	0.0168 (3)	−0.0008 (3)

Bond lengths (Å) top

	Average	Minimum	Maximum
C3a—C4a	2.738 (5)	2.735 (5)	2.741 (5)
C3a—C1a	1.377 (3)	1.377 (3)	1.378 (3)
C3a—C1aⁱ	1.377 (3)	1.377 (3)	1.378 (3)
C3a—C2a	2.389 (4)	2.387 (4)	2.391 (4)
C3a—C2aⁱ	2.389 (4)	2.387 (4)	2.391 (4)
C3a—O1a	2.336 (2)	2.336 (2)	2.336 (3)
C3a—O1aⁱ	2.336 (2)	2.336 (2)	2.336 (3)
C3a—H13a	0.991 (11)	0.990 (11)	0.992 (11)
C3a—H27aⁱⁱ	2.8904 (12)	2.8647 (17)	2.9281 (18)
C3a—H27aⁱⁱⁱ	2.8917 (12)	2.8647 (17)	2.9286 (18)
C4a—C1a	2.368 (5)	2.366 (5)	2.371 (5)
C4a—C1aⁱ	2.368 (5)	2.366 (5)	2.371 (5)
C4a—C2a	1.379 (3)	1.379 (3)	1.380 (4)
C4a—C2aⁱ	1.379 (3)	1.379 (3)	1.380 (4)
C4a—H14a	0.989 (12)	0.988 (12)	0.990 (12)
C4a—H12a	2.0779 (18)	2.0776 (15)	2.078 (2)
C4a—H12a^iv	2.975 (4)	2.941 (4)	2.988 (4)
C4a—H12a^v	2.976 (4)	2.944 (4)	2.988 (4)
C4a—H12aⁱ	2.0779 (18)	2.0776 (15)	2.078 (2)
C4a—H27a^vi	2.9276 (14)	2.8866 (19)	2.9667 (19)
C4a—H27a^vii	2.9292 (14)	2.8870 (19)	2.9667 (19)
C1a—C1aⁱ	2.383 (3)	2.382 (3)	2.383 (3)
C1a—C2a	1.373 (5)	1.371 (5)	1.375 (5)
C1a—C2aⁱ	2.760 (3)	2.759 (3)	2.761 (4)
C1a—O1a	1.360 (4)	1.359 (4)	1.360 (4)
C1a—H13a	2.061 (9)	2.059 (9)	2.063 (9)
C1a—H12a	2.068 (4)	2.066 (4)	2.070 (4)
C1a—H10a	1.951 (14)	1.951 (14)	1.951 (14)
C1a—H15a^vi	2.999 (12)	2.946 (13)	3.043 (12)
C2a—C2aⁱ	2.407 (3)	2.406 (3)	2.407 (3)
C2a—O1a	2.392 (5)	2.390 (5)	2.395 (5)
C2a—H14a	2.053 (10)	2.051 (10)	2.054 (10)
C2a—H12a	1.000 (3)	1.000 (3)	1.001 (3)
C2a—H10a	2.468 (12)	2.467 (13)	2.469 (12)
C2a—H27a^vii	2.988 (2)	2.973 (2)	3.002 (2)
O1a—H13a	2.520 (5)	2.520 (5)	2.521 (5)
O1a—H13a^viii	2.718 (8)	2.699 (8)	2.756 (8)
O1a—H14a^ix	2.462 (7)	2.404 (8)	2.518 (7)
O1a—H12a	2.620 (4)	2.617 (4)	2.623 (4)
O1a—H10a	0.988 (13)	0.987 (13)	0.988 (13)
O1a—N2a^x	2.741 (3)	2.732 (3)	2.758 (3)
O1a—H16a^xi	3.033 (4)	2.915 (3)	3.105 (3)
O1a—H17a^xii	2.929 (3)	2.850 (3)	2.965 (3)
O1a—H27a^xiii	2.957 (4)	2.927 (4)	3.026 (4)
N2a—H10a^xiv	1.788 (15)	1.781 (15)	1.804 (14)
N2a—H10aⁱⁱⁱ	1.788 (15)	1.781 (15)	1.804 (14)
N2a—N2a^xiii	2.4311 (11)	2.4290 (11)	2.4331 (11)
N2a—N1a	2.4242 (14)	2.4232 (14)	2.4253 (14)
N2a—N1a^xv	2.4242 (14)	2.4232 (14)	2.4253 (14)
N2a—C6a	1.4640 (12)	1.4631 (12)	1.4648 (12)
N2a—C5a	2.7988 (19)	2.7983 (19)	2.7992 (19)
N2a—C7a	1.4663 (14)	1.4655 (14)	1.4672 (14)
N2a—C7a^xv	1.4663 (14)	1.4655 (14)	1.4672 (14)
N2a—C7a^xiii	2.8096 (13)	2.8075 (13)	2.8118 (13)
N2a—C7a^xvi	2.8096 (13)	2.8075 (13)	2.8118 (13)
N2a—H16a	2.004 (9)	2.004 (9)	2.005 (9)
N2a—H16a^xv	2.004 (9)	2.004 (9)	2.005 (10)
N2a—H17a	2.0326 (10)	2.0309 (10)	2.0344 (10)
N2a—H17a^xv	2.0326 (10)	2.0309 (10)	2.0344 (10)
N2a—H27a	2.0318 (12)	2.0309 (12)	2.0327 (12)
N2a—H27a^xv	2.0318 (12)	2.0309 (12)	2.0327 (12)
N1a—N1a^xv	2.4242 (16)	2.4221 (16)	2.4263 (16)
N1a—C6a	2.803 (2)	2.803 (2)	2.804 (2)
N1a—C5a	1.4574 (16)	1.4566 (16)	1.4583 (16)
N1a—C7a	1.4590 (16)	1.4582 (16)	1.4599 (16)
N1a—C7a^xv	2.8106 (16)	2.8084 (16)	2.8128 (16)
N1a—C7a^xiii	1.4590 (16)	1.4582 (16)	1.4599 (16)
N1a—C7a^xvi	2.8106 (16)	2.8084 (16)	2.8128 (16)
N1a—H15a	2.022 (11)	2.021 (11)	2.023 (11)
N1a—H15a^xiii	2.022 (11)	2.021 (11)	2.023 (11)
N1a—H17a	2.0254 (15)	2.0245 (15)	2.0262 (15)
N1a—H17a^xiii	2.0254 (15)	2.0245 (15)	2.0262 (15)
N1a—H27a	2.0262 (10)	2.0245 (10)	2.0279 (10)
N1a—H27a^xiii	2.0262 (10)	2.0245 (10)	2.0279 (10)
C6a—H10a^xvii	2.528 (16)	2.485 (16)	2.560 (16)
C6a—H10a^xviii	2.529 (16)	2.485 (16)	2.560 (16)
C6a—H10a^xiv	2.529 (16)	2.485 (16)	2.560 (16)
C6a—H10aⁱⁱⁱ	2.528 (16)	2.485 (16)	2.560 (16)
C6a—C7a	2.3678 (17)	2.3668 (17)	2.3689 (17)
C6a—C7a^xv	2.3678 (17)	2.3668 (17)	2.3689 (17)
C6a—C7a^xiii	2.3678 (17)	2.3668 (17)	2.3689 (17)
C6a—C7a^xvi	2.3678 (17)	2.3668 (17)	2.3689 (17)
C6a—H16a	0.975 (12)	0.975 (12)	0.976 (12)
C6a—H16a^xv	0.975 (12)	0.975 (12)	0.976 (12)
C6a—H17a	2.5867 (11)	2.5849 (11)	2.5885 (11)
C6a—H17a^xv	2.5867 (11)	2.5849 (11)	2.5885 (10)
C6a—H17a^xiii	2.5867 (11)	2.5849 (11)	2.5885 (10)
C6a—H17a^xvi	2.5867 (11)	2.5849 (11)	2.5885 (11)
C5a—C7a	2.3633 (18)	2.3623 (18)	2.3644 (18)
C5a—C7a^xv	2.3633 (18)	2.3623 (18)	2.3644 (18)
C5a—C7a^xiii	2.3633 (18)	2.3623 (18)	2.3644 (18)
C5a—C7a^xvi	2.3633 (18)	2.3623 (18)	2.3644 (18)
C5a—H15a	1.027 (13)	1.027 (13)	1.028 (13)
C5a—H15a^xiii	1.027 (13)	1.027 (13)	1.028 (13)
C5a—H27a	2.5901 (12)	2.5883 (12)	2.5920 (11)
C5a—H27a^xv	2.5901 (12)	2.5883 (12)	2.5920 (12)
C5a—H27a^xiii	2.5901 (12)	2.5883 (12)	2.5920 (12)
C5a—H27a^xvi	2.5901 (12)	2.5883 (12)	2.5920 (12)
C7a—H10a^xiv	2.937 (12)	2.912 (12)	2.995 (12)
C7a—H10aⁱⁱⁱ	2.517 (14)	2.475 (14)	2.535 (14)
C7a—C7a^xv	2.3804 (15)	2.3784 (15)	2.3825 (15)
C7a—C7a^xiii	2.3627 (15)	2.3607 (15)	2.3648 (15)
C7a—H16a^xv	2.561 (11)	2.560 (11)	2.562 (11)
C7a—H15a	2.545 (13)	2.544 (13)	2.545 (13)
C7a—H17a	1.0006 (14)	1.0000 (14)	1.0012 (14)
C7a—H17a^xiii	2.5783 (15)	2.5762 (15)	2.5804 (15)
C7a—H27a	1.0006 (14)	1.0000 (14)	1.0012 (14)
C7a—H27a^xv	2.6065 (16)	2.6044 (15)	2.6087 (15)

Symmetry codes: (i) x₁, −x₂, −x₃, −x₁/2; (ii) −x₁+1/2, −x₂+1/2, x₃−1/2, −x₄; (iii) −x₁+1/2, x₂−1/2, −x₃+1/2, x₁/2; (iv) −x₁−1/2, −x₂+1/2, −x₃, −x₁/2; (v) −x₁−1/2, x₂−1/2, x₃, x₄; (vi) x₁−1/2, x₂−1/2, −x₃+1/2, x₄; (vii) x₁−1/2, −x₂+1/2, x₃−1/2, −x₁/2; (viii) −x₁+1/2, −x₂+1/2, −x₃, −x₁/2; (ix) x₁+1/2, x₂+1/2, x₃, x₁/2; (x) x₁−1/2, x₂+1/2, −x₃+1/2, x₄; (xi) x₁−1/2, x₂+1/2, x₃, x₁/2; (xii) −x₁+1/2, x₂+1/2, −x₃+1/2, x₁/2; (xiii) x₁, x₂, −x₃+1/2, x₁/2; (xiv) x₁+1/2, x₂−1/2, −x₃+1/2, x₄; (xv) −x₁+1, x₂, x₃, x₁/2; (xvi) −x₁+1, x₂, −x₃+1/2, x₄; (xvii) x₁+1/2, x₂−1/2, x₃, x₁/2; (xviii) −x₁+1/2, x₂−1/2, x₃, x₄.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₈N₄O₂
M_r	250.3
Crystal system, space group	Orthorhombic, Xmcm(0β0)s0s†
Temperature (K)	298
Wave vectors	q = 0.37640b*
a, b, c (Å)	10.3474, 7.0763, 16.8321
V (Å³)	1232.5
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.4 × 0.3 × 0.2

Data collection
Diffractometer	IPDS II Stoe diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 3σ(I)] reflections	26753, 2462, 1098
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.690

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.072, 1.66
No. of reflections	2462
No. of parameters	86
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.13

Computer programs: X-AREA (Stoe & Cie GmbH, 2005), SHELXS (Sheldrick, 1997), (Jana2000; Petricek and Dusek, 2000), CrystalMaker (CrystalMaker Software Ltd., 2006).

Selected bond lengths (Å) top

	Average	Minimum	Maximum
C3a—C4a	2.738 (5)	2.735 (5)	2.741 (5)
C3a—C1a	1.377 (3)	1.377 (3)	1.378 (3)
C3a—C1aⁱ	1.377 (3)	1.377 (3)	1.378 (3)
C3a—C2a	2.389 (4)	2.387 (4)	2.391 (4)
C3a—C2aⁱ	2.389 (4)	2.387 (4)	2.391 (4)
C3a—O1a	2.336 (2)	2.336 (2)	2.336 (3)
C3a—O1aⁱ	2.336 (2)	2.336 (2)	2.336 (3)
C3a—H13a	0.991 (11)	0.990 (11)	0.992 (11)
C3a—H27aⁱⁱ	2.8904 (12)	2.8647 (17)	2.9281 (18)
C3a—H27aⁱⁱⁱ	2.8917 (12)	2.8647 (17)	2.9286 (18)
C4a—C1a	2.368 (5)	2.366 (5)	2.371 (5)
C4a—C1aⁱ	2.368 (5)	2.366 (5)	2.371 (5)
C4a—C2a	1.379 (3)	1.379 (3)	1.380 (4)
C4a—C2aⁱ	1.379 (3)	1.379 (3)	1.380 (4)
C4a—H14a	0.989 (12)	0.988 (12)	0.990 (12)
C4a—H12a	2.0779 (18)	2.0776 (15)	2.078 (2)
C4a—H12a^iv	2.975 (4)	2.941 (4)	2.988 (4)
C4a—H12a^v	2.976 (4)	2.944 (4)	2.988 (4)
C4a—H12aⁱ	2.0779 (18)	2.0776 (15)	2.078 (2)
C4a—H27a^vi	2.9276 (14)	2.8866 (19)	2.9667 (19)
C4a—H27a^vii	2.9292 (14)	2.8870 (19)	2.9667 (19)
C1a—C1aⁱ	2.383 (3)	2.382 (3)	2.383 (3)
C1a—C2a	1.373 (5)	1.371 (5)	1.375 (5)
C1a—C2aⁱ	2.760 (3)	2.759 (3)	2.761 (4)
C1a—O1a	1.360 (4)	1.359 (4)	1.360 (4)
C1a—H13a	2.061 (9)	2.059 (9)	2.063 (9)
C1a—H12a	2.068 (4)	2.066 (4)	2.070 (4)
C1a—H10a	1.951 (14)	1.951 (14)	1.951 (14)
C1a—H15a^vi	2.999 (12)	2.946 (13)	3.043 (12)
C2a—C2aⁱ	2.407 (3)	2.406 (3)	2.407 (3)
C2a—O1a	2.392 (5)	2.390 (5)	2.395 (5)
C2a—H14a	2.053 (10)	2.051 (10)	2.054 (10)
C2a—H12a	1.000 (3)	1.000 (3)	1.001 (3)
C2a—H10a	2.468 (12)	2.467 (13)	2.469 (12)
C2a—H27a^vii	2.988 (2)	2.973 (2)	3.002 (2)
O1a—H13a	2.520 (5)	2.520 (5)	2.521 (5)
O1a—H13a^viii	2.718 (8)	2.699 (8)	2.756 (8)
O1a—H14a^ix	2.462 (7)	2.404 (8)	2.518 (7)
O1a—H12a	2.620 (4)	2.617 (4)	2.623 (4)
O1a—H10a	0.988 (13)	0.987 (13)	0.988 (13)
O1a—N2a^x	2.741 (3)	2.732 (3)	2.758 (3)
O1a—H16a^xi	3.033 (4)	2.915 (3)	3.105 (3)
O1a—H17a^xii	2.929 (3)	2.850 (3)	2.965 (3)
O1a—H27a^xiii	2.957 (4)	2.927 (4)	3.026 (4)
N2a—H10a^xiv	1.788 (15)	1.781 (15)	1.804 (14)
N2a—H10aⁱⁱⁱ	1.788 (15)	1.781 (15)	1.804 (14)
N2a—N2a^xiii	2.4311 (11)	2.4290 (11)	2.4331 (11)
N2a—N1a	2.4242 (14)	2.4232 (14)	2.4253 (14)
N2a—N1a^xv	2.4242 (14)	2.4232 (14)	2.4253 (14)
N2a—C6a	1.4640 (12)	1.4631 (12)	1.4648 (12)
N2a—C5a	2.7988 (19)	2.7983 (19)	2.7992 (19)
N2a—C7a	1.4663 (14)	1.4655 (14)	1.4672 (14)
N2a—C7a^xv	1.4663 (14)	1.4655 (14)	1.4672 (14)
N2a—C7a^xiii	2.8096 (13)	2.8075 (13)	2.8118 (13)
N2a—C7a^xvi	2.8096 (13)	2.8075 (13)	2.8118 (13)
N2a—H16a	2.004 (9)	2.004 (9)	2.005 (9)
N2a—H16a^xv	2.004 (9)	2.004 (9)	2.005 (10)
N2a—H17a	2.0326 (10)	2.0309 (10)	2.0344 (10)
N2a—H17a^xv	2.0326 (10)	2.0309 (10)	2.0344 (10)
N2a—H27a	2.0318 (12)	2.0309 (12)	2.0327 (12)
N2a—H27a^xv	2.0318 (12)	2.0309 (12)	2.0327 (12)
N1a—N1a^xv	2.4242 (16)	2.4221 (16)	2.4263 (16)
N1a—C6a	2.803 (2)	2.803 (2)	2.804 (2)
N1a—C5a	1.4574 (16)	1.4566 (16)	1.4583 (16)
N1a—C7a	1.4590 (16)	1.4582 (16)	1.4599 (16)
N1a—C7a^xv	2.8106 (16)	2.8084 (16)	2.8128 (16)
N1a—C7a^xiii	1.4590 (16)	1.4582 (16)	1.4599 (16)
N1a—C7a^xvi	2.8106 (16)	2.8084 (16)	2.8128 (16)
N1a—H15a	2.022 (11)	2.021 (11)	2.023 (11)
N1a—H15a^xiii	2.022 (11)	2.021 (11)	2.023 (11)
N1a—H17a	2.0254 (15)	2.0245 (15)	2.0262 (15)
N1a—H17a^xiii	2.0254 (15)	2.0245 (15)	2.0262 (15)
N1a—H27a	2.0262 (10)	2.0245 (10)	2.0279 (10)
N1a—H27a^xiii	2.0262 (10)	2.0245 (10)	2.0279 (10)
C6a—H10a^xvii	2.528 (16)	2.485 (16)	2.560 (16)
C6a—H10a^xviii	2.529 (16)	2.485 (16)	2.560 (16)
C6a—H10a^xiv	2.529 (16)	2.485 (16)	2.560 (16)
C6a—H10aⁱⁱⁱ	2.528 (16)	2.485 (16)	2.560 (16)
C6a—C7a	2.3678 (17)	2.3668 (17)	2.3689 (17)
C6a—C7a^xv	2.3678 (17)	2.3668 (17)	2.3689 (17)
C6a—C7a^xiii	2.3678 (17)	2.3668 (17)	2.3689 (17)
C6a—C7a^xvi	2.3678 (17)	2.3668 (17)	2.3689 (17)
C6a—H16a	0.975 (12)	0.975 (12)	0.976 (12)
C6a—H16a^xv	0.975 (12)	0.975 (12)	0.976 (12)
C6a—H17a	2.5867 (11)	2.5849 (11)	2.5885 (11)
C6a—H17a^xv	2.5867 (11)	2.5849 (11)	2.5885 (10)
C6a—H17a^xiii	2.5867 (11)	2.5849 (11)	2.5885 (10)
C6a—H17a^xvi	2.5867 (11)	2.5849 (11)	2.5885 (11)
C5a—C7a	2.3633 (18)	2.3623 (18)	2.3644 (18)
C5a—C7a^xv	2.3633 (18)	2.3623 (18)	2.3644 (18)
C5a—C7a^xiii	2.3633 (18)	2.3623 (18)	2.3644 (18)
C5a—C7a^xvi	2.3633 (18)	2.3623 (18)	2.3644 (18)
C5a—H15a	1.027 (13)	1.027 (13)	1.028 (13)
C5a—H15a^xiii	1.027 (13)	1.027 (13)	1.028 (13)
C5a—H27a	2.5901 (12)	2.5883 (12)	2.5920 (11)
C5a—H27a^xv	2.5901 (12)	2.5883 (12)	2.5920 (12)
C5a—H27a^xiii	2.5901 (12)	2.5883 (12)	2.5920 (12)
C5a—H27a^xvi	2.5901 (12)	2.5883 (12)	2.5920 (12)
C7a—H10a^xiv	2.937 (12)	2.912 (12)	2.995 (12)
C7a—H10aⁱⁱⁱ	2.517 (14)	2.475 (14)	2.535 (14)
C7a—C7a^xv	2.3804 (15)	2.3784 (15)	2.3825 (15)
C7a—C7a^xiii	2.3627 (15)	2.3607 (15)	2.3648 (15)
C7a—H16a^xv	2.561 (11)	2.560 (11)	2.562 (11)
C7a—H15a	2.545 (13)	2.544 (13)	2.545 (13)
C7a—H17a	1.0006 (14)	1.0000 (14)	1.0012 (14)
C7a—H17a^xiii	2.5783 (15)	2.5762 (15)	2.5804 (15)
C7a—H27a	1.0006 (14)	1.0000 (14)	1.0012 (14)
C7a—H27a^xv	2.6065 (16)	2.6044 (15)	2.6087 (15)

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