Pyridine 1:1 adducts of urea (Z′ = 1) and thio­urea (Z′ = 8)

During our studies of urea and thio­urea adducts, we noticed that no adducts with unsubstituted pyridine had been structurally investigated. The 1:1 adduct of pyridine and urea, C₅H₅N·CH₄N₂O, crystallizes in the P2₁/c space group with Z = 4. The structure is of a standard type for urea adducts, whereby the urea mol­ecules form a ribbon, parallel to the a axis, consisting of linked R₂²(8) rings, and the pyridine mol­ecules are attached to the periphery of the ribbon by bifurcated (N—H...)₂N hydrogen bonds. The 1:1 adduct of pyridine and thio­urea, C₅H₅N·CH₄N₂S, crystallizes in the P2₁/n space group, with Z = 32 (Z′ = 8). The structure displays similar ribbons to those of the urea adduct. There are two independent ribbons parallel to the b axis at z ≃ 0 and , and three at z ≃ and ; the latter are crosslinked to form a layer structure by additional long N—H...S inter­actions, which each formally replace one branch of a bifurcated hydrogen-bond system.

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015) and publCIF (Westrip, 2010).

Pyridine–urea (1/1) (1)

Crystal data

C5H5N·CH4N2O	F(000) = 296
Mr = 139.16	Dx = 1.265 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.6552 (3) Å	Cell parameters from 8800 reflections
b = 10.7203 (2) Å	θ = 4.8–75.1°
c = 7.4480 (2) Å	µ = 0.75 mm^−1
β = 108.605 (3)°	T = 102 K
V = 730.63 (4) Å^3	Lath, colourless
Z = 4	0.28 × 0.13 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Nova source diffractometer with an Atlas detector	1530 independent reflections
Radiation source: micro-focus sealed X-ray tube	1431 reflections with I > 2σ(I)
Detector resolution: 10.3543 pixels mm^-1	Rint = 0.037
ω scan	θmax = 76.2°, θmin = 4.8°
Absorption correction: multi-scan (Reference)	h = −12→12
Tmin = 0.431, Tmax = 1.000	k = −13→13
15672 measured reflections	l = −9→8

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: mixed
wR(F^2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0427P)^2 + 0.1589P] where P = (Fo^2 + 2Fc^2)/3
1530 reflections	(Δ/σ)max < 0.001
107 parameters	Δρmax = 0.20 e Å^−3
6 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.30600 (8)	0.77804 (6)	0.53819 (9)	0.0294 (2)
N1	0.29569 (11)	0.59533 (8)	0.68760 (12)	0.0329 (2)
H01	0.2925 (14)	0.5142 (11)	0.6784 (18)	0.036 (3)*
H02	0.2957 (14)	0.6331 (12)	0.7909 (17)	0.034 (3)*
C2	0.30338 (10)	0.66144 (9)	0.53760 (13)	0.0252 (2)
N3	0.30818 (10)	0.59468 (8)	0.38648 (12)	0.0293 (2)
H03	0.3066 (14)	0.5141 (11)	0.3933 (18)	0.035 (3)*
H04	0.3133 (14)	0.6318 (11)	0.2841 (17)	0.032 (3)*
N11	0.25285 (11)	0.32953 (8)	0.52225 (14)	0.0367 (2)
C12	0.11263 (13)	0.30075 (11)	0.43972 (18)	0.0409 (3)
H12	0.043954	0.366894	0.402065	0.049*
C13	0.06179 (13)	0.17934 (13)	0.40597 (18)	0.0443 (3)
H13	−0.039217	0.162908	0.346599	0.053*
C14	0.16066 (13)	0.08298 (11)	0.46024 (16)	0.0376 (3)
H14	0.128978	−0.001263	0.440054	0.045*
C15	0.30560 (12)	0.11072 (10)	0.54390 (15)	0.0323 (3)
H15	0.376443	0.046177	0.581111	0.039*
C16	0.34648 (12)	0.23427 (10)	0.57295 (16)	0.0338 (3)
H16	0.446981	0.252687	0.632429	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0453 (4)	0.0200 (4)	0.0249 (4)	−0.0004 (3)	0.0141 (3)	0.0000 (2)
N1	0.0568 (6)	0.0202 (4)	0.0249 (4)	−0.0032 (4)	0.0173 (4)	−0.0012 (3)
C2	0.0290 (5)	0.0228 (5)	0.0236 (5)	−0.0008 (3)	0.0082 (4)	−0.0001 (3)
N3	0.0460 (5)	0.0196 (4)	0.0242 (4)	−0.0008 (3)	0.0142 (4)	−0.0001 (3)
N11	0.0436 (5)	0.0244 (4)	0.0426 (5)	−0.0023 (4)	0.0145 (4)	0.0004 (4)
C12	0.0407 (6)	0.0386 (6)	0.0440 (7)	0.0079 (5)	0.0144 (5)	0.0045 (5)
C13	0.0336 (6)	0.0525 (7)	0.0458 (7)	−0.0089 (5)	0.0111 (5)	−0.0073 (5)
C14	0.0500 (7)	0.0294 (5)	0.0401 (6)	−0.0120 (5)	0.0236 (5)	−0.0095 (4)
C15	0.0437 (6)	0.0263 (5)	0.0310 (5)	0.0022 (4)	0.0176 (5)	0.0031 (4)
C16	0.0341 (5)	0.0300 (5)	0.0351 (5)	−0.0037 (4)	0.0079 (4)	0.0013 (4)

Geometric parameters (Å, º)

O1—C2	1.2502 (12)	C12—C13	1.3854 (17)
N1—C2	1.3450 (13)	C12—H12	0.9500
N1—H01	0.872 (11)	C13—C14	1.3767 (18)
N1—H02	0.870 (11)	C13—H13	0.9500
C2—N3	1.3470 (12)	C14—C15	1.3706 (16)
N3—H03	0.866 (11)	C14—H14	0.9500
N3—H04	0.875 (11)	C15—C16	1.3793 (15)
N11—C12	1.3323 (16)	C15—H15	0.9500
N11—C16	1.3360 (15)	C16—H16	0.9500
C2—N1—H01	118.0 (9)	C14—C13—C12	118.64 (11)
C2—N1—H02	120.4 (9)	C14—C13—H13	120.7
H01—N1—H02	121.6 (12)	C12—C13—H13	120.7
O1—C2—N1	122.03 (9)	C15—C14—C13	118.84 (10)
O1—C2—N3	121.88 (9)	C15—C14—H14	120.6
N1—C2—N3	116.09 (9)	C13—C14—H14	120.6
C2—N3—H03	118.4 (9)	C14—C15—C16	118.64 (10)
C2—N3—H04	120.8 (8)	C14—C15—H15	120.7
H03—N3—H04	120.8 (12)	C16—C15—H15	120.7
C12—N11—C16	116.73 (10)	N11—C16—C15	123.76 (10)
N11—C12—C13	123.39 (11)	N11—C16—H16	118.1
N11—C12—H12	118.3	C15—C16—H16	118.1
C13—C12—H12	118.3
C16—N11—C12—C13	0.16 (18)	C13—C14—C15—C16	0.92 (16)
N11—C12—C13—C14	0.04 (19)	C12—N11—C16—C15	0.21 (17)
C12—C13—C14—C15	−0.59 (18)	C14—C15—C16—N11	−0.76 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···N11	0.87 (1)	2.27 (1)	3.0793 (12)	155 (1)
N3—H03···N11	0.87 (1)	2.33 (1)	3.1197 (12)	152 (1)
N1—H02···O1^i	0.87 (1)	2.05 (1)	2.9164 (11)	177 (1)
N3—H04···O1^ii	0.88 (1)	2.05 (1)	2.9252 (11)	175 (1)
C14—H14···O1^iii	0.95	2.87	3.5317 (14)	127

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2; (iii) x, y−1, z.

Pyridine–thiourea (1/1) (2)

Crystal data

C5H5N·CH4N2S	F(000) = 2624
Mr = 155.22	Dx = 1.294 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 22.115 (1) Å	Cell parameters from 11298 reflections
b = 8.4863 (4) Å	θ = 2.9–30.6°
c = 34.1306 (17) Å	µ = 0.33 mm^−1
β = 95.778 (4)°	T = 100 K
V = 6372.9 (5) Å^3	Block, colourless
Z = 32	0.4 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Eos detector	13032 independent reflections
Radiation source: fine-focus sealed X-ray tube	9855 reflections with I > 2σ(I)
Detector resolution: 16.1419 pixels mm^-1	Rint = 0.082
ω scan	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (Reference)	h = −27→27
Tmin = 0.881, Tmax = 1.000	k = −10→10
142848 measured reflections	l = −42→42

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: mixed
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0278P)^2 + 4.9705P] where P = (Fo^2 + 2Fc^2)/3
13032 reflections	(Δ/σ)max = 0.001
849 parameters	Δρmax = 0.62 e Å^−3
496 restraints	Δρmin = −0.49 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.35748 (3)	0.60605 (7)	0.99756 (2)	0.02239 (14)
N1	0.45615 (10)	0.4737 (2)	1.03477 (6)	0.0211 (4)
H001	0.4918 (8)	0.480 (3)	1.0464 (7)	0.039 (9)*
H002	0.4403 (11)	0.385 (2)	1.0283 (7)	0.026 (7)*
S2	0.40600 (3)	0.10505 (7)	1.00629 (2)	0.01941 (13)
C2	0.42858 (10)	0.6066 (3)	1.02203 (6)	0.0163 (5)
N3	0.45858 (9)	0.7410 (2)	1.02935 (6)	0.0215 (4)
H003	0.4945 (7)	0.739 (3)	1.0401 (7)	0.022 (7)*
H004	0.4421 (10)	0.828 (2)	1.0217 (7)	0.019 (7)*
S3	0.62245 (4)	0.58909 (8)	0.48593 (2)	0.03750 (19)
N4	0.30448 (9)	0.2419 (2)	0.97559 (6)	0.0210 (4)
H005	0.2694 (7)	0.241 (3)	0.9628 (6)	0.024 (7)*
H006	0.3217 (10)	0.328 (2)	0.9822 (7)	0.025 (7)*
S4	0.66172 (3)	0.09288 (7)	0.50672 (2)	0.01924 (13)
C5	0.33361 (10)	0.1067 (3)	0.98340 (6)	0.0161 (5)
S5	0.22744 (3)	0.81554 (7)	0.74391 (2)	0.02026 (14)
N6	0.30475 (9)	−0.0258 (2)	0.97248 (6)	0.0198 (4)
H007	0.2684 (7)	−0.019 (3)	0.9613 (6)	0.019 (7)*
H008	0.3204 (10)	−0.117 (2)	0.9783 (7)	0.023 (7)*
S6	0.47744 (3)	0.68878 (7)	0.73669 (2)	0.01850 (13)
N7	0.70501 (10)	0.4627 (2)	0.53815 (6)	0.0228 (5)
H009	0.7343 (9)	0.468 (3)	0.5565 (6)	0.025 (7)*
H010	0.6903 (10)	0.373 (2)	0.5310 (7)	0.022 (7)*
S7	0.52571 (3)	0.18867 (7)	0.74828 (2)	0.02359 (15)
C8	0.68235 (10)	0.5927 (3)	0.52107 (7)	0.0196 (5)
S8	0.77511 (3)	0.33692 (7)	0.75430 (2)	0.02023 (14)
N9	0.70853 (9)	0.7296 (2)	0.53228 (7)	0.0234 (5)
H011	0.7395 (9)	0.733 (3)	0.5493 (6)	0.031 (8)*
H012	0.6933 (11)	0.817 (2)	0.5237 (7)	0.025 (7)*
N10	0.55887 (10)	0.2264 (2)	0.47727 (6)	0.0219 (5)
H013	0.5248 (9)	0.225 (4)	0.4626 (7)	0.046 (9)*
H014	0.5769 (10)	0.314 (2)	0.4818 (7)	0.021 (7)*
C11	0.58952 (10)	0.0924 (3)	0.48378 (6)	0.0169 (5)
N12	0.56189 (10)	−0.0407 (3)	0.47201 (6)	0.0240 (5)
H015	0.5260 (7)	−0.036 (3)	0.4593 (7)	0.032 (8)*
H016	0.5791 (12)	−0.130 (2)	0.4766 (8)	0.041 (9)*
N13	0.33147 (10)	0.9496 (3)	0.77174 (7)	0.0245 (5)
H017	0.3671 (8)	0.945 (3)	0.7841 (7)	0.037 (8)*
H018	0.3144 (12)	1.038 (2)	0.7664 (8)	0.044 (9)*
C14	0.30148 (10)	0.8156 (3)	0.76387 (6)	0.0171 (5)
N15	0.33136 (9)	0.6815 (2)	0.77197 (6)	0.0199 (4)
H019	0.3691 (7)	0.678 (4)	0.7793 (8)	0.050 (10)*
H020	0.3130 (11)	0.595 (2)	0.7675 (7)	0.031 (8)*
N16	0.57806 (9)	0.5550 (2)	0.77025 (6)	0.0214 (4)
H021	0.6124 (8)	0.561 (3)	0.7851 (7)	0.032 (8)*
H022	0.5599 (10)	0.467 (2)	0.7647 (7)	0.023 (7)*
C17	0.54961 (10)	0.6884 (3)	0.76023 (6)	0.0160 (5)
N18	0.57860 (9)	0.8231 (2)	0.76957 (6)	0.0217 (4)
H023	0.6163 (7)	0.818 (3)	0.7782 (7)	0.031 (8)*
H024	0.5625 (10)	0.912 (2)	0.7640 (7)	0.024 (7)*
N19	0.42818 (11)	0.3181 (3)	0.70984 (8)	0.0350 (6)
H025	0.3941 (9)	0.313 (4)	0.6959 (9)	0.069 (11)*
H026	0.4424 (12)	0.407 (2)	0.7178 (8)	0.036 (8)*
C20	0.45859 (11)	0.1856 (3)	0.71932 (7)	0.0238 (5)
N21	0.43533 (11)	0.0519 (3)	0.70486 (8)	0.0399 (6)
H027	0.4015 (9)	0.053 (4)	0.6906 (8)	0.064 (11)*
H028	0.4497 (12)	−0.037 (2)	0.7135 (8)	0.036 (8)*
N22	0.68147 (10)	0.4728 (3)	0.71279 (6)	0.0234 (5)
H029	0.6474 (8)	0.467 (3)	0.6984 (7)	0.035 (8)*
H030	0.6964 (11)	0.562 (2)	0.7205 (7)	0.032 (8)*
C23	0.70616 (10)	0.3392 (3)	0.72677 (6)	0.0170 (5)
N24	0.67587 (9)	0.2060 (3)	0.71831 (6)	0.0229 (5)
H031	0.6390 (7)	0.210 (3)	0.7084 (7)	0.032 (8)*
H032	0.6909 (11)	0.118 (2)	0.7263 (7)	0.023 (7)*
N31	0.55098 (9)	0.5978 (3)	1.09869 (6)	0.0293 (5)
C32	0.52704 (12)	0.5290 (3)	1.12861 (8)	0.0294 (6)
H32	0.496175	0.452288	1.122728	0.035*
C33	0.54444 (11)	0.5627 (3)	1.16759 (7)	0.0292 (6)
H33	0.526035	0.510343	1.187941	0.035*
C34	0.58889 (12)	0.6733 (3)	1.17638 (8)	0.0330 (6)
H34	0.601530	0.700072	1.202968	0.040*
C35	0.61484 (12)	0.7447 (3)	1.14609 (8)	0.0348 (7)
H35	0.646242	0.820405	1.151371	0.042*
C36	0.59455 (11)	0.7046 (3)	1.10795 (8)	0.0305 (6)
H36	0.612406	0.755391	1.087145	0.037*
N41	0.21202 (10)	0.1318 (3)	0.90870 (6)	0.0421 (7)
C42	0.23560 (12)	0.0622 (3)	0.87907 (8)	0.0351 (7)
H42	0.272076	0.003850	0.884756	0.042*
C43	0.21074 (13)	0.0691 (3)	0.84078 (8)	0.0352 (7)
H43	0.229622	0.018189	0.820416	0.042*
C44	0.15766 (12)	0.1518 (4)	0.83273 (8)	0.0369 (7)
H44	0.138967	0.158988	0.806485	0.044*
C45	0.13186 (12)	0.2239 (3)	0.86281 (8)	0.0346 (7)
H45	0.094949	0.281043	0.857894	0.041*
C46	0.16046 (13)	0.2117 (4)	0.90012 (8)	0.0415 (8)
H46	0.142710	0.262558	0.920956	0.050*
N51	0.79654 (10)	0.5786 (3)	0.60253 (7)	0.0334 (5)
C52	0.79162 (14)	0.5598 (4)	0.64099 (10)	0.0457 (8)
H52	0.758729	0.499323	0.648804	0.055*
C53	0.83318 (17)	0.6258 (4)	0.67027 (8)	0.0531 (10)
H53	0.828899	0.610666	0.697435	0.064*
C54	0.88000 (15)	0.7127 (4)	0.65828 (9)	0.0470 (8)
H54	0.908912	0.759862	0.677194	0.056*
C55	0.88498 (13)	0.7312 (3)	0.61978 (9)	0.0382 (7)
H55	0.917360	0.791352	0.611164	0.046*
C56	0.84334 (12)	0.6631 (3)	0.59328 (8)	0.0314 (6)
H56	0.848049	0.676897	0.566137	0.038*
N61	0.46171 (9)	0.0960 (3)	0.41273 (6)	0.0322 (5)
C62	0.47216 (12)	0.0411 (3)	0.37746 (8)	0.0326 (6)
H62	0.506994	−0.022861	0.375576	0.039*
C63	0.43475 (14)	0.0729 (3)	0.34354 (8)	0.0391 (7)
H63	0.443503	0.031203	0.318904	0.047*
C64	0.38446 (13)	0.1663 (4)	0.34621 (8)	0.0400 (8)
H64	0.357936	0.190524	0.323360	0.048*
C65	0.37322 (12)	0.2237 (3)	0.38206 (8)	0.0357 (7)
H65	0.338781	0.288347	0.384652	0.043*
C66	0.41269 (11)	0.1860 (3)	0.41434 (8)	0.0326 (6)
H66	0.404582	0.226478	0.439236	0.039*
N71	0.42630 (9)	0.8757 (3)	0.83681 (6)	0.0259 (5)
C72	0.39045 (11)	0.8246 (3)	0.86359 (7)	0.0253 (6)
H72	0.350865	0.788486	0.854461	0.030*
C73	0.40757 (12)	0.8213 (3)	0.90368 (7)	0.0288 (6)
H73	0.380567	0.783340	0.921474	0.035*
C74	0.46472 (12)	0.8744 (3)	0.91715 (7)	0.0289 (6)
H74	0.477840	0.874354	0.944523	0.035*
C75	0.50263 (11)	0.9276 (3)	0.89032 (7)	0.0289 (6)
H75	0.542322	0.964612	0.898850	0.035*
C76	0.48171 (11)	0.9262 (3)	0.85068 (7)	0.0275 (6)
H76	0.508100	0.962898	0.832351	0.033*
N81	0.67000 (9)	0.6046 (3)	0.83732 (6)	0.0243 (5)
C82	0.63617 (11)	0.6725 (3)	0.86282 (7)	0.0251 (6)
H82	0.597534	0.713109	0.853066	0.030*
C83	0.65409 (11)	0.6869 (3)	0.90249 (7)	0.0261 (6)
H83	0.628584	0.737018	0.919510	0.031*
C84	0.71013 (11)	0.6268 (3)	0.91699 (7)	0.0261 (6)
H84	0.723625	0.632960	0.944271	0.031*
C85	0.74589 (11)	0.5579 (3)	0.89090 (7)	0.0265 (6)
H85	0.784873	0.517218	0.899833	0.032*
C86	0.72418 (11)	0.5489 (3)	0.85169 (7)	0.0256 (6)
H86	0.749040	0.500630	0.833976	0.031*
N91	0.33109 (11)	0.1539 (3)	0.64790 (8)	0.0476 (7)
C92	0.32951 (15)	0.1830 (4)	0.60776 (12)	0.0565 (10)
H92	0.362488	0.235049	0.597452	0.068*
C93	0.27757 (15)	0.1337 (3)	0.58196 (8)	0.0378 (7)
H93	0.274863	0.152088	0.554378	0.045*
C94	0.23269 (13)	0.0598 (3)	0.59901 (9)	0.0389 (7)
H94	0.197845	0.024419	0.582849	0.047*
C95	0.23577 (15)	0.0354 (4)	0.63708 (10)	0.0478 (8)
H95	0.203493	−0.016135	0.648304	0.057*
C96	0.28394 (15)	0.0830 (4)	0.65948 (9)	0.0456 (8)
H96	0.284421	0.063728	0.686928	0.055*
N101	0.58170 (10)	0.4063 (3)	0.65106 (6)	0.0297 (5)
C102	0.60672 (11)	0.3337 (3)	0.62232 (8)	0.0278 (6)
H102	0.646026	0.289164	0.628062	0.033*
C103	0.57852 (12)	0.3193 (3)	0.58426 (7)	0.0284 (6)
H103	0.598032	0.265911	0.564553	0.034*
C104	0.52173 (12)	0.3841 (3)	0.57573 (7)	0.0305 (6)
H104	0.501523	0.377869	0.549866	0.037*
C105	0.49475 (12)	0.4579 (3)	0.60523 (8)	0.0306 (6)
H105	0.455140	0.501369	0.600285	0.037*
C106	0.52607 (12)	0.4678 (3)	0.64214 (8)	0.0301 (6)
H106	0.507382	0.520761	0.662273	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0268 (3)	0.0139 (3)	0.0241 (3)	−0.0015 (2)	−0.0086 (2)	0.0010 (2)
N1	0.0220 (11)	0.0147 (11)	0.0253 (12)	−0.0004 (9)	−0.0035 (9)	−0.0010 (9)
S2	0.0195 (3)	0.0132 (3)	0.0243 (3)	0.0001 (2)	−0.0038 (2)	−0.0019 (2)
C2	0.0223 (12)	0.0146 (11)	0.0123 (11)	−0.0024 (10)	0.0037 (9)	−0.0019 (9)
N3	0.0186 (11)	0.0137 (11)	0.0312 (12)	0.0005 (9)	−0.0018 (9)	0.0002 (9)
S3	0.0542 (5)	0.0136 (3)	0.0380 (4)	−0.0013 (3)	−0.0279 (3)	−0.0010 (3)
N4	0.0199 (11)	0.0138 (11)	0.0277 (12)	−0.0021 (9)	−0.0058 (9)	−0.0018 (9)
S4	0.0199 (3)	0.0130 (3)	0.0233 (3)	0.0000 (2)	−0.0058 (2)	−0.0011 (2)
C5	0.0227 (12)	0.0165 (12)	0.0093 (11)	0.0004 (10)	0.0026 (9)	−0.0010 (9)
S5	0.0188 (3)	0.0152 (3)	0.0250 (3)	0.0007 (2)	−0.0067 (2)	−0.0009 (2)
N6	0.0198 (11)	0.0136 (11)	0.0247 (11)	−0.0012 (9)	−0.0040 (9)	−0.0016 (9)
S6	0.0159 (3)	0.0169 (3)	0.0216 (3)	0.0008 (2)	−0.0034 (2)	0.0012 (2)
N7	0.0232 (11)	0.0132 (11)	0.0302 (13)	−0.0029 (9)	−0.0066 (9)	0.0016 (9)
S7	0.0227 (3)	0.0165 (3)	0.0293 (3)	0.0015 (2)	−0.0085 (3)	−0.0022 (3)
C8	0.0235 (12)	0.0180 (12)	0.0176 (12)	0.0000 (10)	0.0039 (10)	−0.0008 (10)
S8	0.0174 (3)	0.0181 (3)	0.0237 (3)	0.0003 (2)	−0.0055 (2)	0.0000 (2)
N9	0.0205 (11)	0.0134 (11)	0.0342 (13)	0.0027 (9)	−0.0072 (10)	0.0002 (9)
N10	0.0213 (11)	0.0146 (11)	0.0279 (12)	0.0001 (9)	−0.0066 (9)	−0.0010 (9)
C11	0.0207 (12)	0.0148 (11)	0.0152 (11)	−0.0011 (10)	0.0013 (9)	0.0007 (9)
N12	0.0220 (11)	0.0161 (11)	0.0317 (13)	−0.0016 (9)	−0.0082 (9)	−0.0020 (9)
N13	0.0199 (11)	0.0176 (12)	0.0336 (13)	−0.0020 (9)	−0.0097 (9)	0.0037 (9)
C14	0.0196 (12)	0.0191 (12)	0.0121 (11)	0.0009 (10)	−0.0007 (9)	0.0010 (9)
N15	0.0184 (11)	0.0159 (11)	0.0241 (11)	0.0009 (9)	−0.0044 (9)	−0.0006 (9)
N16	0.0197 (11)	0.0163 (11)	0.0263 (12)	0.0014 (9)	−0.0070 (9)	−0.0008 (9)
C17	0.0199 (12)	0.0173 (12)	0.0112 (11)	0.0021 (10)	0.0043 (9)	0.0022 (9)
N18	0.0163 (11)	0.0172 (11)	0.0302 (12)	−0.0011 (9)	−0.0034 (9)	0.0037 (9)
N19	0.0290 (13)	0.0162 (12)	0.0546 (16)	−0.0004 (10)	−0.0212 (12)	0.0057 (11)
C20	0.0267 (13)	0.0160 (12)	0.0270 (13)	−0.0028 (10)	−0.0054 (10)	0.0025 (10)
N21	0.0361 (14)	0.0153 (12)	0.0616 (18)	−0.0038 (11)	−0.0286 (13)	0.0046 (11)
N22	0.0235 (11)	0.0182 (11)	0.0259 (12)	0.0022 (9)	−0.0105 (9)	−0.0031 (9)
C23	0.0180 (11)	0.0210 (12)	0.0118 (11)	0.0022 (10)	−0.0002 (9)	−0.0024 (9)
N24	0.0200 (11)	0.0175 (11)	0.0289 (12)	−0.0018 (9)	−0.0085 (9)	0.0011 (9)
N31	0.0230 (11)	0.0407 (14)	0.0240 (12)	0.0067 (10)	0.0016 (9)	0.0003 (10)
C32	0.0257 (14)	0.0265 (14)	0.0362 (16)	−0.0023 (11)	0.0041 (12)	−0.0059 (12)
C33	0.0286 (14)	0.0333 (15)	0.0271 (14)	0.0063 (12)	0.0093 (11)	0.0094 (12)
C34	0.0271 (14)	0.0449 (18)	0.0263 (14)	0.0072 (13)	−0.0010 (11)	−0.0086 (13)
C35	0.0253 (14)	0.0320 (16)	0.0470 (18)	−0.0045 (12)	0.0031 (13)	−0.0058 (13)
C36	0.0243 (14)	0.0331 (15)	0.0351 (16)	0.0049 (12)	0.0085 (11)	0.0124 (13)
N41	0.0233 (12)	0.084 (2)	0.0188 (12)	−0.0059 (13)	−0.0002 (9)	−0.0029 (12)
C42	0.0240 (14)	0.0460 (18)	0.0362 (16)	0.0093 (13)	0.0076 (12)	0.0138 (14)
C43	0.0434 (17)	0.0375 (17)	0.0270 (15)	−0.0050 (14)	0.0144 (13)	−0.0090 (13)
C44	0.0338 (16)	0.0525 (19)	0.0230 (14)	−0.0147 (14)	−0.0048 (12)	0.0099 (13)
C45	0.0194 (13)	0.0368 (17)	0.0478 (18)	0.0024 (12)	0.0052 (12)	0.0115 (14)
C46	0.0292 (15)	0.060 (2)	0.0370 (17)	−0.0079 (15)	0.0126 (13)	−0.0228 (15)
N51	0.0251 (12)	0.0408 (14)	0.0334 (13)	−0.0017 (11)	−0.0019 (10)	−0.0005 (11)
C52	0.0379 (17)	0.0422 (19)	0.061 (2)	0.0083 (15)	0.0259 (16)	0.0232 (16)
C53	0.087 (3)	0.058 (2)	0.0156 (15)	0.044 (2)	0.0090 (16)	0.0105 (14)
C54	0.059 (2)	0.0377 (18)	0.0396 (19)	0.0110 (16)	−0.0187 (16)	−0.0160 (15)
C55	0.0331 (16)	0.0328 (16)	0.0467 (19)	−0.0036 (13)	−0.0049 (13)	0.0011 (14)
C56	0.0273 (14)	0.0438 (17)	0.0234 (14)	0.0051 (13)	0.0037 (11)	0.0082 (12)
N61	0.0223 (11)	0.0535 (16)	0.0204 (11)	0.0015 (11)	−0.0009 (9)	0.0022 (11)
C62	0.0295 (14)	0.0337 (16)	0.0360 (16)	0.0038 (12)	0.0102 (12)	0.0043 (13)
C63	0.060 (2)	0.0369 (17)	0.0206 (14)	−0.0185 (15)	0.0048 (13)	−0.0051 (12)
C64	0.0418 (17)	0.0429 (18)	0.0312 (16)	−0.0168 (15)	−0.0173 (13)	0.0141 (14)
C65	0.0254 (14)	0.0354 (16)	0.0449 (18)	0.0005 (12)	−0.0026 (12)	0.0074 (14)
C66	0.0233 (14)	0.0476 (18)	0.0273 (14)	−0.0031 (13)	0.0041 (11)	−0.0064 (13)
N71	0.0214 (11)	0.0361 (13)	0.0199 (11)	0.0017 (10)	−0.0005 (9)	0.0002 (9)
C72	0.0169 (12)	0.0321 (15)	0.0266 (14)	0.0011 (11)	0.0012 (10)	−0.0026 (11)
C73	0.0309 (14)	0.0337 (15)	0.0233 (14)	0.0039 (12)	0.0093 (11)	0.0000 (12)
C74	0.0339 (15)	0.0301 (15)	0.0215 (13)	0.0112 (12)	−0.0037 (11)	−0.0035 (11)
C75	0.0190 (13)	0.0330 (15)	0.0332 (15)	0.0023 (11)	−0.0050 (11)	−0.0040 (12)
C76	0.0203 (13)	0.0369 (16)	0.0263 (14)	0.0013 (12)	0.0066 (10)	0.0023 (12)
N81	0.0215 (11)	0.0309 (12)	0.0200 (11)	−0.0010 (9)	−0.0003 (8)	−0.0006 (9)
C82	0.0195 (12)	0.0279 (14)	0.0276 (14)	0.0054 (11)	0.0012 (10)	0.0045 (11)
C83	0.0285 (14)	0.0283 (14)	0.0227 (13)	0.0016 (11)	0.0085 (11)	−0.0012 (11)
C84	0.0305 (14)	0.0305 (15)	0.0165 (12)	−0.0043 (12)	−0.0013 (10)	0.0002 (11)
C85	0.0184 (12)	0.0321 (15)	0.0280 (14)	0.0021 (11)	−0.0026 (10)	0.0043 (11)
C86	0.0204 (13)	0.0316 (15)	0.0256 (14)	0.0015 (11)	0.0062 (10)	0.0000 (11)
N91	0.0327 (14)	0.0631 (19)	0.0421 (16)	0.0082 (13)	−0.0203 (12)	−0.0136 (14)
C92	0.044 (2)	0.0267 (17)	0.106 (3)	0.0014 (15)	0.041 (2)	0.0058 (18)
C93	0.062 (2)	0.0361 (17)	0.0155 (13)	0.0209 (15)	0.0024 (13)	0.0036 (12)
C94	0.0355 (16)	0.0347 (17)	0.0450 (19)	0.0056 (13)	−0.0029 (14)	−0.0147 (14)
C95	0.055 (2)	0.0388 (19)	0.050 (2)	0.0009 (16)	0.0103 (17)	−0.0075 (15)
C96	0.056 (2)	0.049 (2)	0.0332 (17)	0.0122 (17)	0.0099 (15)	0.0114 (15)
N101	0.0279 (12)	0.0380 (13)	0.0223 (11)	−0.0058 (10)	−0.0020 (9)	−0.0009 (10)
C102	0.0193 (12)	0.0285 (14)	0.0349 (15)	0.0002 (11)	−0.0006 (11)	0.0012 (12)
C103	0.0319 (14)	0.0285 (15)	0.0262 (14)	−0.0024 (12)	0.0096 (11)	−0.0054 (11)
C104	0.0351 (15)	0.0354 (16)	0.0194 (13)	−0.0086 (13)	−0.0053 (11)	−0.0011 (12)
C105	0.0205 (13)	0.0350 (16)	0.0355 (16)	0.0020 (11)	−0.0015 (11)	−0.0015 (12)
C106	0.0260 (14)	0.0393 (16)	0.0260 (14)	−0.0011 (12)	0.0070 (11)	−0.0075 (12)

Geometric parameters (Å, º)

S1—C2	1.704 (2)	C43—H43	0.9500
N1—C2	1.334 (3)	C44—C45	1.368 (4)
N1—H001	0.848 (14)	C44—H44	0.9500
N1—H002	0.852 (14)	C45—C46	1.368 (4)
S2—C5	1.709 (2)	C45—H45	0.9500
C2—N3	1.330 (3)	C46—H46	0.9500
N3—H003	0.842 (13)	N51—C56	1.323 (3)
N3—H004	0.849 (13)	N51—C52	1.338 (4)
S3—C8	1.696 (2)	C52—C53	1.405 (5)
N4—C5	1.330 (3)	C52—H52	0.9500
N4—H005	0.851 (13)	C53—C54	1.367 (5)
N4—H006	0.847 (14)	C53—H53	0.9500
S4—C11	1.706 (2)	C54—C55	1.338 (4)
C5—N6	1.327 (3)	C54—H54	0.9500
S5—C14	1.709 (2)	C55—C56	1.354 (4)
N6—H007	0.857 (13)	C55—H55	0.9500
N6—H008	0.860 (14)	C56—H56	0.9500
S6—C17	1.713 (2)	N61—C66	1.332 (3)
N7—C8	1.322 (3)	N61—C62	1.333 (3)
N7—H009	0.855 (13)	C62—C63	1.380 (4)
N7—H010	0.852 (14)	C62—H62	0.9500
S7—C20	1.699 (2)	C63—C64	1.376 (4)
C8—N9	1.337 (3)	C63—H63	0.9500
S8—C23	1.709 (2)	C64—C65	1.363 (4)
N9—H011	0.852 (14)	C64—H64	0.9500
N9—H012	0.853 (14)	C65—C66	1.373 (4)
N10—C11	1.331 (3)	C65—H65	0.9500
N10—H013	0.861 (14)	C66—H66	0.9500
N10—H014	0.853 (14)	N71—C76	1.339 (3)
C11—N12	1.327 (3)	N71—C72	1.341 (3)
N12—H015	0.866 (14)	C72—C73	1.383 (3)
N12—H016	0.852 (14)	C72—H72	0.9500
N13—C14	1.330 (3)	C73—C74	1.377 (4)
N13—H017	0.857 (14)	C73—H73	0.9500
N13—H018	0.853 (14)	C74—C75	1.378 (4)
C14—N15	1.331 (3)	C74—H74	0.9500
N15—H019	0.847 (14)	C75—C76	1.385 (3)
N15—H020	0.848 (14)	C75—H75	0.9500
N16—C17	1.323 (3)	C76—H76	0.9500
N16—H021	0.871 (14)	N81—C82	1.334 (3)
N16—H022	0.859 (14)	N81—C86	1.335 (3)
C17—N18	1.333 (3)	C82—C83	1.377 (3)
N18—H023	0.857 (14)	C82—H82	0.9500
N18—H024	0.847 (14)	C83—C84	1.385 (3)
N19—C20	1.334 (3)	C83—H83	0.9500
N19—H025	0.851 (14)	C84—C85	1.379 (3)
N19—H026	0.849 (14)	C84—H84	0.9500
C20—N21	1.320 (3)	C85—C86	1.378 (3)
N21—H027	0.851 (14)	C85—H85	0.9500
N21—H028	0.859 (14)	C86—H86	0.9500
N22—C23	1.326 (3)	N91—C96	1.299 (4)
N22—H029	0.858 (14)	N91—C92	1.389 (4)
N22—H030	0.855 (14)	C92—C93	1.438 (5)
C23—N24	1.331 (3)	C92—H92	0.9500
N24—H031	0.851 (14)	C93—C94	1.354 (4)
N24—H032	0.850 (14)	C93—H93	0.9500
N31—C32	1.331 (3)	C94—C95	1.311 (4)
N31—C36	1.337 (3)	C94—H94	0.9500
C32—C33	1.377 (4)	C95—C96	1.311 (4)
C32—H32	0.9500	C95—H95	0.9500
C33—C34	1.370 (4)	C96—H96	0.9500
C33—H33	0.9500	N101—C102	1.326 (3)
C34—C35	1.373 (4)	N101—C106	1.343 (3)
C34—H34	0.9500	C102—C103	1.388 (3)
C35—C36	1.376 (4)	C102—H102	0.9500
C35—H35	0.9500	C103—C104	1.375 (4)
C36—H36	0.9500	C103—H103	0.9500
N41—C42	1.322 (3)	C104—C105	1.372 (4)
N41—C46	1.333 (4)	C104—H104	0.9500
C42—C43	1.367 (4)	C105—C106	1.378 (4)
C42—H42	0.9500	C105—H105	0.9500
C43—C44	1.372 (4)	C106—H106	0.9500
C2—N1—H001	118 (2)	C44—C45—H45	120.8
C2—N1—H002	120.2 (18)	N41—C46—C45	123.2 (3)
H001—N1—H002	121 (3)	N41—C46—H46	118.4
N3—C2—N1	117.4 (2)	C45—C46—H46	118.4
N3—C2—S1	120.82 (18)	C56—N51—C52	116.2 (2)
N1—C2—S1	121.76 (18)	N51—C52—C53	122.6 (3)
C2—N3—H003	120.0 (18)	N51—C52—H52	118.7
C2—N3—H004	119.6 (17)	C53—C52—H52	118.7
H003—N3—H004	120 (2)	C54—C53—C52	117.6 (3)
C5—N4—H005	119.8 (18)	C54—C53—H53	121.2
C5—N4—H006	120.0 (18)	C52—C53—H53	121.2
H005—N4—H006	120 (2)	C55—C54—C53	119.8 (3)
N6—C5—N4	117.7 (2)	C55—C54—H54	120.1
N6—C5—S2	121.56 (18)	C53—C54—H54	120.1
N4—C5—S2	120.73 (18)	C54—C55—C56	119.2 (3)
C5—N6—H007	117.9 (17)	C54—C55—H55	120.4
C5—N6—H008	121.6 (17)	C56—C55—H55	120.4
H007—N6—H008	120 (2)	N51—C56—C55	124.6 (3)
C8—N7—H009	120.4 (18)	N51—C56—H56	117.7
C8—N7—H010	119.9 (17)	C55—C56—H56	117.7
H009—N7—H010	120 (2)	C66—N61—C62	117.0 (2)
N7—C8—N9	117.7 (2)	N61—C62—C63	123.1 (3)
N7—C8—S3	122.10 (19)	N61—C62—H62	118.5
N9—C8—S3	120.20 (18)	C63—C62—H62	118.5
C8—N9—H011	121.1 (19)	C64—C63—C62	118.5 (3)
C8—N9—H012	120.6 (17)	C64—C63—H63	120.8
H011—N9—H012	118 (3)	C62—C63—H63	120.8
C11—N10—H013	119 (2)	C65—C64—C63	119.1 (3)
C11—N10—H014	119.8 (17)	C65—C64—H64	120.4
H013—N10—H014	119 (3)	C63—C64—H64	120.4
N12—C11—N10	117.8 (2)	C64—C65—C66	118.6 (3)
N12—C11—S4	121.46 (18)	C64—C65—H65	120.7
N10—C11—S4	120.78 (18)	C66—C65—H65	120.7
C11—N12—H015	118.9 (19)	N61—C66—C65	123.7 (2)
C11—N12—H016	121 (2)	N61—C66—H66	118.1
H015—N12—H016	120 (3)	C65—C66—H66	118.1
C14—N13—H017	118.6 (19)	C76—N71—C72	116.5 (2)
C14—N13—H018	121 (2)	N71—C72—C73	124.0 (2)
H017—N13—H018	121 (3)	N71—C72—H72	118.0
N13—C14—N15	117.5 (2)	C73—C72—H72	118.0
N13—C14—S5	121.27 (18)	C74—C73—C72	118.3 (2)
N15—C14—S5	121.22 (18)	C74—C73—H73	120.8
C14—N15—H019	123 (2)	C72—C73—H73	120.8
C14—N15—H020	119.1 (18)	C73—C74—C75	119.0 (2)
H019—N15—H020	118 (3)	C73—C74—H74	120.5
C17—N16—H021	117.7 (19)	C75—C74—H74	120.5
C17—N16—H022	119.1 (17)	C74—C75—C76	118.7 (2)
H021—N16—H022	123 (2)	C74—C75—H75	120.6
N16—C17—N18	117.8 (2)	C76—C75—H75	120.6
N16—C17—S6	121.27 (18)	N71—C76—C75	123.5 (2)
N18—C17—S6	120.90 (17)	N71—C76—H76	118.3
C17—N18—H023	118.0 (18)	C75—C76—H76	118.3
C17—N18—H024	121.8 (17)	C82—N81—C86	117.1 (2)
H023—N18—H024	119 (3)	N81—C82—C83	123.7 (2)
C20—N19—H025	119 (2)	N81—C82—H82	118.1
C20—N19—H026	120.5 (19)	C83—C82—H82	118.1
H025—N19—H026	120 (3)	C82—C83—C84	118.5 (2)
N21—C20—N19	117.8 (2)	C82—C83—H83	120.7
N21—C20—S7	121.02 (19)	C84—C83—H83	120.7
N19—C20—S7	121.18 (19)	C85—C84—C83	118.4 (2)
C20—N21—H027	120 (2)	C85—C84—H84	120.8
C20—N21—H028	120.6 (19)	C83—C84—H84	120.8
H027—N21—H028	118 (3)	C86—C85—C84	119.0 (2)
C23—N22—H029	117.8 (19)	C86—C85—H85	120.5
C23—N22—H030	120.8 (18)	C84—C85—H85	120.5
H029—N22—H030	121 (3)	N81—C86—C85	123.3 (2)
N22—C23—N24	117.9 (2)	N81—C86—H86	118.3
N22—C23—S8	121.33 (18)	C85—C86—H86	118.3
N24—C23—S8	120.76 (18)	C96—N91—C92	116.2 (3)
C23—N24—H031	119.6 (19)	N91—C92—C93	119.5 (3)
C23—N24—H032	120.3 (17)	N91—C92—H92	120.3
H031—N24—H032	119 (3)	C93—C92—H92	120.3
C32—N31—C36	116.7 (2)	C94—C93—C92	116.5 (3)
N31—C32—C33	123.8 (3)	C94—C93—H93	121.7
N31—C32—H32	118.1	C92—C93—H93	121.7
C33—C32—H32	118.1	C95—C94—C93	122.1 (3)
C34—C33—C32	118.6 (2)	C95—C94—H94	118.9
C34—C33—H33	120.7	C93—C94—H94	118.9
C32—C33—H33	120.7	C96—C95—C94	119.2 (3)
C33—C34—C35	118.9 (2)	C96—C95—H95	120.4
C33—C34—H34	120.6	C94—C95—H95	120.4
C35—C34—H34	120.6	N91—C96—C95	126.5 (3)
C34—C35—C36	118.8 (3)	N91—C96—H96	116.7
C34—C35—H35	120.6	C95—C96—H96	116.7
C36—C35—H35	120.6	C102—N101—C106	117.0 (2)
N31—C36—C35	123.3 (2)	N101—C102—C103	123.5 (2)
N31—C36—H36	118.3	N101—C102—H102	118.3
C35—C36—H36	118.3	C103—C102—H102	118.3
C42—N41—C46	117.0 (2)	C104—C103—C102	118.5 (2)
N41—C42—C43	124.1 (3)	C104—C103—H103	120.7
N41—C42—H42	118.0	C102—C103—H103	120.7
C43—C42—H42	118.0	C105—C104—C103	118.8 (2)
C42—C43—C44	117.8 (2)	C105—C104—H104	120.6
C42—C43—H43	121.1	C103—C104—H104	120.6
C44—C43—H43	121.1	C104—C105—C106	118.9 (2)
C45—C44—C43	119.4 (2)	C104—C105—H105	120.6
C45—C44—H44	120.3	C106—C105—H105	120.6
C43—C44—H44	120.3	N101—C106—C105	123.3 (2)
C46—C45—C44	118.4 (3)	N101—C106—H106	118.4
C46—C45—H45	120.8	C105—C106—H106	118.4
C36—N31—C32—C33	0.4 (4)	C76—N71—C72—C73	−0.2 (4)
N31—C32—C33—C34	0.1 (4)	N71—C72—C73—C74	0.4 (4)
C32—C33—C34—C35	−0.8 (4)	C72—C73—C74—C75	−0.4 (4)
C33—C34—C35—C36	1.1 (4)	C73—C74—C75—C76	0.2 (4)
C32—N31—C36—C35	0.0 (4)	C72—N71—C76—C75	−0.1 (4)
C34—C35—C36—N31	−0.7 (4)	C74—C75—C76—N71	0.1 (4)
C46—N41—C42—C43	0.7 (5)	C86—N81—C82—C83	−0.2 (4)
N41—C42—C43—C44	−0.8 (5)	N81—C82—C83—C84	−0.5 (4)
C42—C43—C44—C45	0.2 (4)	C82—C83—C84—C85	1.2 (4)
C43—C44—C45—C46	0.5 (4)	C83—C84—C85—C86	−1.1 (4)
C42—N41—C46—C45	0.0 (5)	C82—N81—C86—C85	0.3 (4)
C44—C45—C46—N41	−0.6 (5)	C84—C85—C86—N81	0.4 (4)
C56—N51—C52—C53	0.3 (4)	C96—N91—C92—C93	−0.4 (4)
N51—C52—C53—C54	0.2 (5)	N91—C92—C93—C94	−0.3 (4)
C52—C53—C54—C55	−0.4 (5)	C92—C93—C94—C95	0.7 (4)
C53—C54—C55—C56	0.0 (5)	C93—C94—C95—C96	−0.5 (5)
C52—N51—C56—C55	−0.8 (4)	C92—N91—C96—C95	0.7 (5)
C54—C55—C56—N51	0.6 (5)	C94—C95—C96—N91	−0.3 (5)
C66—N61—C62—C63	−0.3 (4)	C106—N101—C102—C103	0.2 (4)
N61—C62—C63—C64	0.4 (4)	N101—C102—C103—C104	0.2 (4)
C62—C63—C64—C65	−0.2 (4)	C102—C103—C104—C105	−1.1 (4)
C63—C64—C65—C66	0.1 (4)	C103—C104—C105—C106	1.5 (4)
C62—N61—C66—C65	0.2 (4)	C102—N101—C106—C105	0.3 (4)
C64—C65—C66—N61	0.0 (4)	C104—C105—C106—N101	−1.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H001···N31	0.85 (1)	2.33 (2)	3.057 (3)	144 (3)
N1—H002···S2	0.85 (1)	2.58 (1)	3.427 (2)	173 (2)
N3—H003···N31	0.84 (1)	2.55 (2)	3.206 (3)	136 (2)
N3—H004···S2^i	0.85 (1)	2.53 (1)	3.367 (2)	171 (2)
N4—H005···N41	0.85 (1)	2.33 (2)	3.054 (3)	144 (2)
N4—H006···S1	0.85 (1)	2.52 (1)	3.363 (2)	171 (2)
N6—H007···N41	0.86 (1)	2.44 (2)	3.136 (3)	139 (2)
N6—H008···S1^ii	0.86 (1)	2.56 (1)	3.414 (2)	175 (2)
N7—H009···N51	0.86 (1)	2.19 (2)	2.999 (3)	157 (2)
N7—H010···S4	0.85 (1)	2.58 (1)	3.422 (2)	171 (2)
N9—H011···N51	0.85 (1)	2.48 (2)	3.200 (3)	143 (2)
N9—H012···S4^i	0.85 (1)	2.50 (1)	3.340 (2)	170 (2)
N10—H013···N61	0.86 (1)	2.36 (2)	3.121 (3)	148 (3)
N10—H014···S3	0.85 (1)	2.54 (1)	3.384 (2)	172 (2)
N12—H015···N61	0.87 (1)	2.31 (2)	3.073 (3)	147 (2)
N12—H016···S3^ii	0.85 (1)	2.58 (2)	3.429 (2)	174 (3)
N13—H017···N71	0.86 (1)	2.20 (2)	2.964 (3)	149 (2)
N13—H018···S5^iii	0.85 (1)	2.54 (2)	3.389 (2)	174 (3)
N15—H019···S6	0.85 (1)	2.93 (2)	3.560 (2)	133 (2)
N15—H020···S5^iv	0.85 (1)	2.55 (2)	3.390 (2)	172 (2)
N16—H021···N81	0.87 (1)	2.12 (2)	2.935 (3)	156 (2)
N16—H022···S7	0.86 (1)	2.53 (2)	3.375 (2)	170 (2)
N18—H023···S8^v	0.86 (1)	2.75 (2)	3.417 (2)	136 (2)
N18—H024···S7^i	0.85 (1)	2.53 (1)	3.369 (2)	174 (2)
N19—H025···N91	0.85 (1)	2.45 (2)	3.179 (3)	145 (3)
N19—H026···S6	0.85 (1)	2.58 (2)	3.423 (2)	174 (3)
N21—H027···N91	0.85 (1)	2.20 (2)	2.990 (3)	155 (3)
N21—H028···S6^ii	0.86 (1)	2.51 (2)	3.367 (2)	172 (2)
N22—H029···N101	0.86 (1)	2.13 (2)	2.948 (3)	160 (3)
N22—H030···S8^v	0.86 (1)	2.55 (2)	3.393 (2)	172 (2)
N24—H031···S7	0.85 (1)	2.98 (2)	3.575 (2)	129 (2)
N24—H032···S8^vi	0.85 (1)	2.57 (1)	3.414 (2)	173 (2)

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1/2, y−1/2, −z+3/2; (v) −x+3/2, y+1/2, −z+3/2; (vi) −x+3/2, y−1/2, −z+3/2.