Tris[4-(dimethyl-amino)-pyridinium] hexa-kis-(thio-cyanato-κN)ferrate(III) monohydrate.

In the title compound, (C7H11N2)3[Fe(NCS)6]·H2O, the Fe(III) cation is coordinated by six terminal N-bonded thio-cyanate anions into a discrete threefold negatively charged complex. Charge balance is achieved by three protonated 4-(dimethyl-amino)-pyridine cations. The asymmetric unit consists of one Fe(III) cation, six thio-cyanate anions, three 4-(dimethyl-amino)-pyridinium cations and one water mol-ecule, all of them located in general positions.

Related literature

For general background to our work on the synthesis and characterization of coordination compounds based on trans­ition metal thio­cyanates and neutral N-donor co-ligands such as pyridine, see: Boeckmann & Näther (2011 ▶, 2012 ▶).

Experimental

Crystal data

(C7H11N2)3[Fe(NCS)6]·H2O

M = 791.88

Triclinic,

a = 11.5780 (7) Å

b = 11.7620 (7) Å

c = 16.5450 (11) Å

α = 81.260 (7)°

β = 71.550 (7)°

γ = 62.950 (6)°

V = 1903.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.77 mm−1

T = 180 K

0.13 × 0.08 × 0.06 mm

Data collection

Stoe IPDS-1 diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ▶) T min = 0.808, T max = 0.947

13617 measured reflections

7356 independent reflections

4936 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.104

S = 0.95

7356 reflections

431 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.50 e Å−3

Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2012 ▶); software used to prepare material for publication: XCIF in SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049574/hp2051sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049574/hp2051Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C7H11N2)3[Fe(NCS)6]·H2O	Z = 2
Mr = 791.88	F(000) = 822
Triclinic, P1	Dx = 1.382 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.5780 (7) Å	Cell parameters from 13617 reflections
b = 11.7620 (7) Å	θ = 2.4–26.0°
c = 16.5450 (11) Å	µ = 0.77 mm−1
α = 81.260 (7)°	T = 180 K
β = 71.550 (7)°	Block, red
γ = 62.950 (6)°	0.13 × 0.08 × 0.06 mm
V = 1903.4 (2) Å3

Stoe IPDS-1 diffractometer	7356 independent reflections
Radiation source: fine-focus sealed tube	4936 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
phi scan	θmax = 26.0°, θmin = 2.4°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)	h = −14→14
Tmin = 0.808, Tmax = 0.947	k = −14→14
13617 measured reflections	l = −20→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.052P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.001
7356 reflections	Δρmax = 0.34 e Å−3
431 parameters	Δρmin = −0.50 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (11)

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. 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Fe1	0.98269 (4)	0.75134 (4)	0.75439 (2)	0.01991 (12)
N1	1.1616 (3)	0.7621 (3)	0.68821 (16)	0.0302 (6)
C1	1.2706 (3)	0.7490 (3)	0.65317 (18)	0.0254 (6)
S1	1.42277 (9)	0.72966 (11)	0.60257 (6)	0.0479 (2)
N2	0.9072 (2)	0.8295 (2)	0.65142 (16)	0.0281 (5)
C2	0.8775 (3)	0.8660 (3)	0.58809 (18)	0.0226 (6)
S2	0.83393 (8)	0.91910 (8)	0.50092 (5)	0.0360 (2)
N3	0.8051 (3)	0.7391 (3)	0.82393 (16)	0.0291 (6)
C3	0.6995 (3)	0.7518 (3)	0.86786 (17)	0.0250 (6)
S3	0.55149 (8)	0.77201 (10)	0.93009 (5)	0.0430 (2)
N4	1.0601 (2)	0.5739 (2)	0.70384 (16)	0.0276 (5)
C4	1.0898 (3)	0.4916 (3)	0.65919 (17)	0.0223 (6)
S4	1.12768 (8)	0.37586 (7)	0.59908 (5)	0.02920 (18)
N5	1.0629 (2)	0.6720 (2)	0.85664 (16)	0.0280 (5)
C5	1.1078 (3)	0.6329 (3)	0.91418 (18)	0.0243 (6)
S5	1.17023 (8)	0.57453 (8)	0.99515 (5)	0.0352 (2)
N6	0.9021 (3)	0.9292 (2)	0.80598 (15)	0.0279 (5)
C6	0.8648 (3)	1.0174 (3)	0.84754 (17)	0.0233 (6)
S6	0.81802 (9)	1.14057 (7)	0.90350 (5)	0.0349 (2)
N10	0.8102 (3)	0.6969 (2)	1.06431 (16)	0.0300 (6)
H10	0.8080	0.6393	1.0374	0.036*
C11	0.8352 (3)	0.6680 (3)	1.14068 (19)	0.0287 (6)
H11	0.8516	0.5851	1.1642	0.034*
C12	0.8376 (3)	0.7546 (3)	1.18468 (17)	0.0232 (6)
H12	0.8539	0.7326	1.2390	0.028*
C13	0.8157 (3)	0.8783 (3)	1.14994 (16)	0.0198 (5)
C14	0.7897 (3)	0.9043 (3)	1.06899 (18)	0.0289 (6)
H14	0.7731	0.9860	1.0432	0.035*
C15	0.7884 (3)	0.8131 (3)	1.02853 (19)	0.0310 (7)
H15	0.7719	0.8313	0.9742	0.037*
C16	0.8466 (3)	0.9423 (3)	1.27260 (18)	0.0295 (6)
H16A	0.7616	0.9703	1.3185	0.044*
H16B	0.8965	0.9894	1.2756	0.044*
H16C	0.9012	0.8507	1.2789	0.044*
C17	0.7972 (4)	1.0927 (3)	1.1516 (2)	0.0345 (7)
H17A	0.8679	1.0823	1.0977	0.052*
H17B	0.8018	1.1450	1.1902	0.052*
H17C	0.7085	1.1347	1.1407	0.052*
N11	0.8174 (2)	0.9670 (2)	1.19072 (15)	0.0252 (5)
N20	0.8066 (3)	0.2006 (3)	0.55337 (16)	0.0324 (6)
H20	0.8113	0.1424	0.5231	0.039*
C21	0.7879 (3)	0.3170 (3)	0.51934 (19)	0.0337 (7)
H21	0.7819	0.3344	0.4625	0.040*
C22	0.7775 (3)	0.4096 (3)	0.56454 (19)	0.0290 (6)
H22	0.7631	0.4915	0.5395	0.035*
C23	0.7880 (3)	0.3847 (3)	0.64942 (17)	0.0221 (6)
C24	0.8093 (3)	0.2608 (3)	0.68218 (18)	0.0247 (6)
H24	0.8173	0.2392	0.7385	0.030*
C25	0.8183 (3)	0.1721 (3)	0.6331 (2)	0.0299 (7)
H25	0.8331	0.0889	0.6556	0.036*
C26	0.7592 (4)	0.6008 (3)	0.6599 (2)	0.0384 (8)
H26A	0.8331	0.5927	0.6081	0.058*
H26B	0.7588	0.6519	0.7017	0.058*
H26C	0.6729	0.6429	0.6458	0.058*
C27	0.8000 (3)	0.4446 (3)	0.78040 (19)	0.0327 (7)
H27A	0.7285	0.4235	0.8192	0.049*
H27B	0.7979	0.5188	0.8020	0.049*
H27C	0.8880	0.3716	0.7768	0.049*
N21	0.7785 (2)	0.4741 (2)	0.69564 (15)	0.0253 (5)
N30	0.4772 (3)	0.3824 (4)	0.7836 (2)	0.0598 (10)
H30	0.4722	0.4477	0.8067	0.072*
C31	0.5092 (4)	0.2694 (5)	0.8242 (3)	0.0573 (12)
H31	0.5254	0.2614	0.8781	0.069*
C32	0.5190 (3)	0.1663 (4)	0.7905 (2)	0.0459 (9)
H32	0.5446	0.0866	0.8199	0.055*
C33	0.4912 (3)	0.1771 (3)	0.7116 (2)	0.0328 (7)
C34	0.4594 (3)	0.2978 (3)	0.6703 (2)	0.0399 (8)
H34	0.4428	0.3095	0.6162	0.048*
C35	0.4524 (4)	0.3966 (4)	0.7073 (3)	0.0530 (10)
H35	0.4298	0.4773	0.6792	0.064*
C36	0.4696 (4)	0.0904 (4)	0.5952 (2)	0.0456 (9)
H36A	0.5426	0.1023	0.5505	0.068*
H36B	0.3832	0.1638	0.5954	0.068*
H36C	0.4665	0.0124	0.5842	0.068*
C37	0.5321 (4)	−0.0459 (4)	0.7194 (3)	0.0544 (10)
H37A	0.4772	−0.0370	0.7790	0.082*
H37B	0.6279	−0.0837	0.7172	0.082*
H37C	0.5163	−0.1014	0.6898	0.082*
N31	0.4946 (3)	0.0793 (3)	0.67822 (18)	0.0371 (6)
O1	0.4555 (3)	0.5701 (4)	0.8757 (3)	0.0986 (15)
H1O1	0.4927	0.6104	0.8866	0.148*
H2O1	0.4004	0.5649	0.9218	0.148*

	U11	U22	U33	U12	U13	U23
Fe1	0.0247 (2)	0.0191 (2)	0.0198 (2)	−0.01218 (16)	−0.00614 (15)	−0.00240 (14)
N1	0.0341 (14)	0.0365 (15)	0.0283 (13)	−0.0208 (12)	−0.0074 (11)	−0.0083 (11)
C1	0.0323 (16)	0.0266 (15)	0.0241 (14)	−0.0169 (12)	−0.0104 (12)	0.0002 (11)
S1	0.0299 (4)	0.0642 (6)	0.0518 (5)	−0.0269 (4)	−0.0040 (4)	−0.0013 (5)
N2	0.0338 (13)	0.0265 (13)	0.0273 (13)	−0.0148 (11)	−0.0110 (11)	0.0017 (10)
C2	0.0217 (13)	0.0208 (14)	0.0264 (15)	−0.0090 (11)	−0.0067 (11)	−0.0044 (11)
S2	0.0438 (4)	0.0392 (5)	0.0268 (4)	−0.0141 (4)	−0.0178 (3)	−0.0017 (3)
N3	0.0332 (13)	0.0349 (15)	0.0273 (13)	−0.0215 (11)	−0.0065 (11)	−0.0043 (11)
C3	0.0336 (16)	0.0305 (15)	0.0203 (13)	−0.0187 (13)	−0.0124 (12)	−0.0001 (11)
S3	0.0322 (4)	0.0695 (6)	0.0321 (4)	−0.0292 (4)	−0.0023 (3)	−0.0044 (4)
N4	0.0339 (13)	0.0223 (12)	0.0309 (13)	−0.0154 (11)	−0.0085 (10)	−0.0027 (11)
C4	0.0268 (13)	0.0198 (14)	0.0214 (13)	−0.0117 (11)	−0.0074 (11)	0.0029 (11)
S4	0.0450 (4)	0.0209 (4)	0.0222 (3)	−0.0143 (3)	−0.0089 (3)	−0.0030 (3)
N5	0.0342 (13)	0.0249 (13)	0.0293 (13)	−0.0135 (11)	−0.0136 (11)	0.0004 (10)
C5	0.0279 (14)	0.0224 (14)	0.0271 (15)	−0.0139 (12)	−0.0066 (12)	−0.0058 (12)
S5	0.0428 (4)	0.0408 (5)	0.0301 (4)	−0.0193 (4)	−0.0193 (3)	0.0007 (3)
N6	0.0359 (13)	0.0257 (13)	0.0258 (12)	−0.0173 (11)	−0.0066 (10)	−0.0022 (10)
C6	0.0322 (14)	0.0204 (14)	0.0190 (13)	−0.0138 (12)	−0.0069 (11)	0.0020 (11)
S6	0.0600 (5)	0.0223 (4)	0.0203 (4)	−0.0178 (4)	−0.0078 (3)	−0.0022 (3)
N10	0.0403 (14)	0.0309 (14)	0.0256 (13)	−0.0194 (11)	−0.0085 (10)	−0.0081 (11)
C11	0.0323 (15)	0.0252 (15)	0.0304 (15)	−0.0148 (12)	−0.0068 (12)	−0.0013 (12)
C12	0.0280 (14)	0.0235 (14)	0.0202 (13)	−0.0132 (11)	−0.0074 (11)	0.0019 (11)
C13	0.0214 (12)	0.0244 (14)	0.0160 (12)	−0.0131 (11)	−0.0026 (10)	−0.0015 (10)
C14	0.0411 (16)	0.0313 (16)	0.0210 (14)	−0.0206 (14)	−0.0116 (12)	0.0031 (12)
C15	0.0397 (16)	0.0410 (18)	0.0215 (14)	−0.0240 (14)	−0.0113 (12)	0.0018 (13)
C16	0.0463 (17)	0.0311 (16)	0.0231 (14)	−0.0233 (14)	−0.0173 (13)	0.0042 (12)
C17	0.0528 (19)	0.0267 (16)	0.0351 (17)	−0.0228 (15)	−0.0206 (15)	0.0050 (13)
N11	0.0372 (13)	0.0233 (12)	0.0227 (12)	−0.0169 (11)	−0.0136 (10)	0.0027 (10)
N20	0.0379 (14)	0.0362 (15)	0.0299 (13)	−0.0198 (12)	−0.0073 (11)	−0.0119 (11)
C21	0.0413 (17)	0.046 (2)	0.0214 (14)	−0.0245 (15)	−0.0095 (12)	−0.0028 (13)
C22	0.0389 (16)	0.0320 (16)	0.0243 (14)	−0.0217 (14)	−0.0130 (12)	0.0068 (12)
C23	0.0216 (13)	0.0240 (14)	0.0226 (13)	−0.0119 (11)	−0.0049 (10)	−0.0020 (11)
C24	0.0274 (14)	0.0264 (15)	0.0215 (13)	−0.0136 (12)	−0.0055 (11)	−0.0001 (11)
C25	0.0332 (15)	0.0250 (15)	0.0342 (16)	−0.0156 (13)	−0.0060 (12)	−0.0051 (13)
C26	0.056 (2)	0.0208 (15)	0.050 (2)	−0.0160 (15)	−0.0328 (17)	0.0054 (14)
C27	0.0446 (18)	0.0310 (16)	0.0286 (15)	−0.0173 (14)	−0.0153 (13)	−0.0037 (13)
N21	0.0325 (12)	0.0214 (12)	0.0271 (12)	−0.0126 (10)	−0.0135 (10)	−0.0003 (10)
N30	0.0410 (18)	0.078 (3)	0.065 (2)	−0.0339 (18)	0.0046 (16)	−0.029 (2)
C31	0.039 (2)	0.098 (4)	0.037 (2)	−0.035 (2)	−0.0031 (16)	−0.005 (2)
C32	0.0353 (17)	0.067 (3)	0.0351 (18)	−0.0254 (18)	−0.0102 (14)	0.0108 (17)
C33	0.0196 (13)	0.0413 (18)	0.0308 (16)	−0.0127 (13)	−0.0040 (11)	0.0096 (13)
C34	0.0363 (17)	0.0393 (19)	0.0416 (19)	−0.0166 (15)	−0.0113 (14)	0.0073 (15)
C35	0.0395 (19)	0.047 (2)	0.068 (3)	−0.0205 (18)	−0.0082 (18)	0.002 (2)
C36	0.0387 (18)	0.050 (2)	0.043 (2)	−0.0155 (17)	−0.0080 (15)	−0.0057 (17)
C37	0.043 (2)	0.037 (2)	0.069 (3)	−0.0123 (17)	−0.0146 (18)	0.0185 (19)
N31	0.0301 (13)	0.0305 (14)	0.0393 (15)	−0.0082 (11)	−0.0050 (11)	0.0044 (12)
O1	0.066 (2)	0.123 (3)	0.122 (3)	−0.065 (2)	0.020 (2)	−0.064 (3)

Fe1—N4	2.052 (2)	N20—H20	0.8800
Fe1—N6	2.059 (2)	C21—C22	1.353 (4)
Fe1—N2	2.061 (3)	C21—H21	0.9500
Fe1—N1	2.065 (3)	C22—C23	1.422 (4)
Fe1—N3	2.072 (3)	C22—H22	0.9500
Fe1—N5	2.079 (2)	C23—N21	1.338 (4)
N1—C1	1.157 (4)	C23—C24	1.413 (4)
C1—S1	1.618 (3)	C24—C25	1.365 (4)
N2—C2	1.165 (4)	C24—H24	0.9500
C2—S2	1.620 (3)	C25—H25	0.9500
N3—C3	1.162 (4)	C26—N21	1.461 (4)
C3—S3	1.625 (3)	C26—H26A	0.9800
N4—C4	1.164 (4)	C26—H26B	0.9800
C4—S4	1.621 (3)	C26—H26C	0.9800
N5—C5	1.162 (4)	C27—N21	1.464 (4)
C5—S5	1.634 (3)	C27—H27A	0.9800
N6—C6	1.165 (4)	C27—H27B	0.9800
C6—S6	1.620 (3)	C27—H27C	0.9800
N10—C11	1.345 (4)	N30—C31	1.339 (6)
N10—C15	1.347 (4)	N30—C35	1.351 (6)
N10—H10	0.8800	N30—H30	0.8800
C11—C12	1.353 (4)	C31—C32	1.355 (7)
C11—H11	0.9500	C31—H31	0.9500
C12—C13	1.419 (4)	C32—C33	1.415 (5)
C12—H12	0.9500	C32—H32	0.9500
C13—N11	1.336 (4)	C33—N31	1.330 (5)
C13—C14	1.423 (4)	C33—C34	1.418 (5)
C14—C15	1.356 (4)	C34—C35	1.354 (6)
C14—H14	0.9500	C34—H34	0.9500
C15—H15	0.9500	C35—H35	0.9500
C16—N11	1.454 (4)	C36—N31	1.467 (5)
C16—H16A	0.9800	C36—H36A	0.9800
C16—H16B	0.9800	C36—H36B	0.9800
C16—H16C	0.9800	C36—H36C	0.9800
C17—N11	1.466 (4)	C37—N31	1.457 (5)
C17—H17A	0.9800	C37—H37A	0.9800
C17—H17B	0.9800	C37—H37B	0.9800
C17—H17C	0.9800	C37—H37C	0.9800
N20—C25	1.344 (4)	O1—H1O1	0.8400
N20—C21	1.346 (4)	O1—H2O1	0.8401
N4—Fe1—N6	179.11 (11)	N20—C21—H21	119.3
N4—Fe1—N2	88.68 (10)	C22—C21—H21	119.3
N6—Fe1—N2	91.24 (10)	C21—C22—C23	120.1 (3)
N4—Fe1—N1	89.09 (10)	C21—C22—H22	119.9
N6—Fe1—N1	91.80 (10)	C23—C22—H22	119.9
N2—Fe1—N1	90.15 (10)	N21—C23—C24	121.8 (3)
N4—Fe1—N3	91.19 (10)	N21—C23—C22	121.6 (3)
N6—Fe1—N3	87.92 (10)	C24—C23—C22	116.6 (3)
N2—Fe1—N3	91.48 (10)	C25—C24—C23	120.1 (3)
N1—Fe1—N3	178.35 (10)	C25—C24—H24	119.9
N4—Fe1—N5	91.08 (10)	C23—C24—H24	119.9
N6—Fe1—N5	89.02 (10)	N20—C25—C24	121.1 (3)
N2—Fe1—N5	178.77 (10)	N20—C25—H25	119.5
N1—Fe1—N5	88.64 (10)	C24—C25—H25	119.5
N3—Fe1—N5	89.73 (10)	N21—C26—H26A	109.5
C1—N1—Fe1	170.0 (3)	N21—C26—H26B	109.5
N1—C1—S1	178.9 (3)	H26A—C26—H26B	109.5
C2—N2—Fe1	173.1 (2)	N21—C26—H26C	109.5
N2—C2—S2	178.9 (3)	H26A—C26—H26C	109.5
C3—N3—Fe1	168.7 (2)	H26B—C26—H26C	109.5
N3—C3—S3	178.9 (3)	N21—C27—H27A	109.5
C4—N4—Fe1	162.8 (2)	N21—C27—H27B	109.5
N4—C4—S4	178.3 (3)	H27A—C27—H27B	109.5
C5—N5—Fe1	176.9 (2)	N21—C27—H27C	109.5
N5—C5—S5	178.4 (3)	H27A—C27—H27C	109.5
C6—N6—Fe1	167.6 (2)	H27B—C27—H27C	109.5
N6—C6—S6	177.9 (3)	C23—N21—C26	120.9 (2)
C11—N10—C15	120.8 (2)	C23—N21—C27	121.1 (2)
C11—N10—H10	119.6	C26—N21—C27	117.7 (2)
C15—N10—H10	119.6	C31—N30—C35	120.3 (4)
N10—C11—C12	121.4 (3)	C31—N30—H30	119.9
N10—C11—H11	119.3	C35—N30—H30	119.9
C12—C11—H11	119.3	N30—C31—C32	121.8 (4)
C11—C12—C13	120.2 (3)	N30—C31—H31	119.1
C11—C12—H12	119.9	C32—C31—H31	119.1
C13—C12—H12	119.9	C31—C32—C33	120.1 (4)
N11—C13—C12	122.5 (2)	C31—C32—H32	120.0
N11—C13—C14	121.2 (3)	C33—C32—H32	120.0
C12—C13—C14	116.3 (2)	N31—C33—C32	121.8 (3)
C15—C14—C13	120.4 (3)	N31—C33—C34	121.9 (3)
C15—C14—H14	119.8	C32—C33—C34	116.3 (3)
C13—C14—H14	119.8	C35—C34—C33	120.4 (4)
N10—C15—C14	120.9 (3)	C35—C34—H34	119.8
N10—C15—H15	119.5	C33—C34—H34	119.8
C14—C15—H15	119.5	N30—C35—C34	121.1 (4)
N11—C16—H16A	109.5	N30—C35—H35	119.4
N11—C16—H16B	109.5	C34—C35—H35	119.4
H16A—C16—H16B	109.5	N31—C36—H36A	109.5
N11—C16—H16C	109.5	N31—C36—H36B	109.5
H16A—C16—H16C	109.5	H36A—C36—H36B	109.5
H16B—C16—H16C	109.5	N31—C36—H36C	109.5
N11—C17—H17A	109.5	H36A—C36—H36C	109.5
N11—C17—H17B	109.5	H36B—C36—H36C	109.5
H17A—C17—H17B	109.5	N31—C37—H37A	109.5
N11—C17—H17C	109.5	N31—C37—H37B	109.5
H17A—C17—H17C	109.5	H37A—C37—H37B	109.5
H17B—C17—H17C	109.5	N31—C37—H37C	109.5
C13—N11—C16	122.4 (2)	H37A—C37—H37C	109.5
C13—N11—C17	120.6 (2)	H37B—C37—H37C	109.5
C16—N11—C17	116.9 (2)	C33—N31—C37	121.7 (3)
C25—N20—C21	120.7 (3)	C33—N31—C36	121.3 (3)
C25—N20—H20	119.6	C37—N31—C36	116.8 (3)
C21—N20—H20	119.6	H1O1—O1—H2O1	105.9
N20—C21—C22	121.3 (3)