1,8-Bis(dimethyl­ethyleneguanidino)naphthalene

The title compound, C₂₀H₂₆N₆, obtained from the reaction of o-phenyl­enediamine with commercially available 2-chloro-1,3-dimethyl­imidazolinium chloride, crystallizes with three independent mol­ecules in the asymmetric unit. In each mol­ecule, the two nitro­gen heterocycles are syn oriented with respect to the naphthalene fragment and have centroid–centroid separations in the range 3.280 (4)–3.395 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.060
• wR factor = 0.169
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT411_ALERT_2_C Short Inter H...H Contact  H25    ..  H33A    ..       2.13 Ang.

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           28.32
           From the CIF: _reflns_number_total              12973
           From the CIF: _diffrn_reflns_limit_ max hkl   10.   38.   23.
           From the CIF: _diffrn_reflns_limit_ min hkl  -10.  -46.  -12.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   11.   48.   23.
           Calculated minimum hkl  -11.  -48.  -23.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1,8-Bis(dimethylethyleneguanidino)naphthalene

Crystal data

C20H26N6	F(000) = 2256
Mr = 350.47	Dx = 1.274 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4589 (12) Å	Cell parameters from 3205 reflections
b = 36.168 (5) Å	θ = 2.3–28.0°
c = 17.943 (2) Å	µ = 0.08 mm^−1
β = 92.642 (2)°	T = 90 K
V = 5483.5 (13) Å^3	Block, pink
Z = 12	0.40 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	7208 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
Graphite monochromator	θmax = 28.3°, θmin = 1.1°
φ and ω scans	h = −10→10
33635 measured reflections	k = −46→38
12973 independent reflections	l = −12→23

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0468P)^2 + 0.0265P] where P = (Fo^2 + 2Fc^2)/3
12973 reflections	(Δ/σ)max = 0.001
715 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

Experimental. IR (KBr, cm^-1): 3420 (N—CH₃), 1600 (C=N); ¹H NMR (400 MHz, CDCl₃): 2.58 (12H, s, 4 x N—CH₃), 3.24 (8H, s, 4 x N—CH₂), 6.70 (2H, dd, J=7.3, 1.3 Hz, 2 x Ar—H), 7.19 (2H, dd, J=7.7, 2 x Ar—H), 7.29 (2H, dd, J=8.1, 1.1 Hz, 2 x Ar—H); ¹³C NMR (100 MHz, CDCl₃): 34.9 (CH₃), 48.5 (CH₂), 117.9 (CH), 120.6 (CH), 124.6 (C), 125.5 (CH), 136.6 (C), 148.4 (C), 151.0 (C); Analysis calculated for C₂₀H₂₆N₆: C 68.54, H 7.48, N 23.98%; found: C 68.48, H 7.46, N 24.01%.

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
C1	0.1916 (3)	0.12364 (6)	0.32832 (12)	0.0197 (5)
C2	0.3257 (3)	0.12770 (6)	0.28162 (11)	0.0185 (5)
C3	0.4851 (3)	0.11670 (6)	0.30206 (12)	0.0193 (5)
C4	0.6027 (3)	0.12245 (6)	0.25208 (12)	0.0236 (5)
C5	0.5723 (3)	0.13903 (6)	0.18269 (13)	0.0245 (5)
C6	0.4222 (3)	0.14946 (6)	0.16099 (12)	0.0239 (5)
C7	0.2966 (3)	0.14426 (6)	0.20939 (12)	0.0203 (5)
C8	0.1421 (3)	0.15558 (6)	0.18537 (12)	0.0219 (5)
C9	0.0181 (3)	0.15059 (6)	0.23067 (12)	0.0243 (6)
C10	0.0438 (3)	0.13475 (6)	0.30136 (12)	0.0222 (5)
C11	0.2561 (3)	0.11645 (6)	0.45881 (12)	0.0201 (5)
C12	0.2684 (3)	0.18430 (6)	0.44630 (13)	0.0263 (6)
C13	0.3504 (3)	0.15050 (7)	0.56072 (13)	0.0309 (6)
C14	0.3609 (3)	0.10981 (7)	0.58011 (12)	0.0289 (6)
C15	0.2600 (3)	0.05395 (6)	0.51198 (13)	0.0265 (6)
C16	0.6335 (3)	0.10545 (6)	0.41453 (12)	0.0204 (5)
C17	0.6807 (3)	0.04139 (6)	0.45106 (13)	0.0285 (6)
C18	0.8400 (3)	0.09385 (7)	0.50105 (13)	0.0289 (6)
C19	0.8233 (3)	0.13518 (7)	0.49149 (13)	0.0289 (6)
C20	0.6617 (3)	0.17417 (6)	0.40298 (13)	0.0281 (6)
C21	0.4391 (3)	0.22899 (6)	0.64914 (12)	0.0214 (5)
C22	0.5700 (3)	0.24098 (6)	0.60592 (12)	0.0212 (5)
C23	0.7280 (3)	0.22552 (6)	0.61157 (12)	0.0232 (5)
C24	0.8424 (3)	0.23934 (7)	0.56641 (13)	0.0308 (6)
C25	0.8115 (3)	0.26864 (7)	0.51702 (13)	0.0332 (6)
C26	0.6645 (3)	0.28357 (7)	0.51006 (13)	0.0299 (6)
C27	0.5413 (3)	0.27026 (6)	0.55316 (12)	0.0231 (5)
C28	0.3892 (3)	0.28654 (7)	0.54481 (13)	0.0270 (6)
C29	0.2678 (3)	0.27391 (7)	0.58440 (13)	0.0291 (6)
C30	0.2923 (3)	0.24480 (7)	0.63512 (13)	0.0275 (6)
C31	0.5222 (3)	0.20027 (6)	0.76357 (13)	0.0231 (5)
C32	0.5296 (3)	0.26607 (7)	0.79817 (14)	0.0350 (6)
C33	0.6541 (3)	0.21700 (7)	0.87543 (13)	0.0342 (6)
C34	0.6526 (3)	0.17528 (7)	0.86889 (14)	0.0352 (7)
C35	0.5244 (3)	0.13274 (7)	0.77254 (14)	0.0341 (6)
C36	0.8796 (3)	0.19397 (6)	0.70515 (13)	0.0237 (5)
C37	0.9125 (3)	0.12697 (7)	0.69445 (14)	0.0363 (7)
C38	1.0825 (3)	0.16672 (7)	0.77755 (14)	0.0345 (6)
C39	1.0748 (3)	0.20744 (7)	0.79726 (14)	0.0318 (6)
C40	0.9255 (3)	0.26049 (6)	0.74263 (13)	0.0287 (6)
C41	0.7665 (3)	0.06384 (6)	0.88973 (12)	0.0196 (5)
C42	0.9272 (3)	0.07610 (6)	0.90434 (12)	0.0185 (5)
C43	1.0584 (3)	0.06739 (6)	0.85834 (12)	0.0203 (5)
C44	1.2067 (3)	0.08131 (6)	0.87736 (13)	0.0253 (5)
C45	1.2363 (3)	0.10308 (7)	0.94100 (13)	0.0260 (6)
C46	1.1169 (3)	0.11115 (6)	0.98657 (13)	0.0248 (5)
C47	0.9616 (3)	0.09810 (6)	0.96960 (12)	0.0206 (5)
C48	0.8394 (3)	0.10673 (6)	1.01858 (12)	0.0225 (5)
C49	0.6892 (3)	0.09427 (6)	1.00399 (12)	0.0246 (5)
C50	0.6531 (3)	0.07305 (6)	0.94033 (12)	0.0228 (5)
C51	0.6342 (3)	0.01778 (6)	0.81598 (12)	0.0182 (5)
C52	0.6902 (3)	−0.01762 (7)	0.93420 (12)	0.0260 (6)
C53	0.5192 (3)	−0.03992 (6)	0.82809 (12)	0.0239 (5)
C54	0.4528 (3)	−0.02205 (6)	0.75704 (13)	0.0253 (5)
C55	0.5190 (3)	0.03673 (7)	0.69501 (12)	0.0278 (6)
C56	1.0207 (2)	0.01324 (6)	0.78321 (12)	0.0198 (5)
C57	0.9420 (3)	0.01926 (7)	0.65076 (12)	0.0297 (6)
C58	0.9462 (3)	−0.04053 (6)	0.72063 (12)	0.0257 (6)
C59	1.0120 (3)	−0.05048 (6)	0.79784 (12)	0.0258 (6)
C60	1.1048 (3)	−0.01248 (6)	0.90673 (12)	0.0250 (5)
N1	0.1990 (2)	0.10467 (5)	0.39623 (10)	0.0204 (4)
N2	0.3233 (2)	0.14997 (5)	0.47970 (10)	0.0245 (5)
N3	0.2584 (2)	0.09370 (5)	0.52120 (10)	0.0223 (4)
N4	0.5214 (2)	0.09662 (5)	0.36723 (10)	0.0199 (4)
N5	0.6880 (2)	0.08032 (5)	0.46856 (10)	0.0240 (5)
N6	0.7200 (2)	0.13770 (5)	0.42398 (10)	0.0230 (4)
N7	0.4479 (2)	0.19966 (5)	0.69992 (10)	0.0237 (5)
N8	0.5972 (2)	0.22920 (5)	0.80148 (10)	0.0257 (5)
N9	0.5387 (2)	0.16902 (6)	0.80681 (11)	0.0291 (5)
N10	0.7643 (2)	0.19481 (5)	0.65627 (10)	0.0242 (5)
N11	0.9306 (2)	0.16101 (5)	0.73754 (11)	0.0283 (5)
N12	0.9716 (2)	0.22207 (5)	0.73632 (10)	0.0258 (5)
N13	0.7198 (2)	0.04685 (5)	0.82261 (10)	0.0205 (4)
N14	0.5937 (2)	−0.00871 (5)	0.86736 (10)	0.0210 (4)
N15	0.5657 (2)	0.00775 (5)	0.74716 (10)	0.0208 (4)
N16	1.0418 (2)	0.04798 (5)	0.79039 (10)	0.0206 (4)
N17	1.0022 (2)	−0.00272 (5)	0.71334 (10)	0.0223 (4)
N18	1.0139 (2)	−0.01470 (5)	0.83588 (10)	0.0212 (4)
H4	0.7077	0.1148	0.2655	0.028*
H5	0.6565	0.1431	0.1504	0.029*
H6	0.4019	0.1602	0.1132	0.029*
H8	0.1246	0.1667	0.1377	0.026*
H9	−0.0856	0.1579	0.2141	0.029*
H10	−0.0439	0.1315	0.3319	0.027*
H12A	0.1581	0.1886	0.4584	0.032*
H12B	0.2757	0.1829	0.3920	0.032*
H12C	0.3343	0.2047	0.4658	0.032*
H13A	0.2615	0.1625	0.5853	0.037*
H13B	0.4500	0.1635	0.5753	0.037*
H14A	0.4707	0.1005	0.5782	0.035*
H14B	0.3208	0.1048	0.6301	0.035*
H15A	0.3687	0.0456	0.5055	0.032*
H15B	0.1936	0.0472	0.4679	0.032*
H15C	0.2186	0.0422	0.5563	0.032*
H17A	0.5778	0.0356	0.4265	0.034*
H17B	0.7651	0.0351	0.4176	0.034*
H17C	0.6944	0.0270	0.4972	0.034*
H18A	0.9301	0.0842	0.4736	0.035*
H18B	0.8541	0.0870	0.5544	0.035*
H19A	0.7737	0.1466	0.5348	0.035*
H19B	0.9270	0.1470	0.4844	0.035*
H20A	0.5661	0.1717	0.3704	0.034*
H20B	0.6367	0.1880	0.4479	0.034*
H20C	0.7431	0.1874	0.3764	0.034*
H24	0.9450	0.2286	0.5691	0.037*
H25	0.8938	0.2781	0.4882	0.040*
H26	0.6443	0.3032	0.4758	0.036*
H28	0.3721	0.3065	0.5111	0.032*
H29	0.1659	0.2848	0.5778	0.035*
H30	0.2048	0.2356	0.6608	0.033*
H32A	0.4368	0.2670	0.8289	0.042*
H32B	0.4978	0.2721	0.7464	0.042*
H32C	0.6085	0.2840	0.8171	0.042*
H33A	0.5828	0.2255	0.9142	0.041*
H33B	0.7623	0.2263	0.8876	0.041*
H34A	0.7585	0.1656	0.8577	0.042*
H34B	0.6176	0.1636	0.9152	0.042*
H35A	0.4209	0.1221	0.7826	0.041*
H35B	0.5343	0.1350	0.7185	0.041*
H35C	0.6083	0.1166	0.7933	0.041*
H37A	0.9947	0.1258	0.6578	0.044*
H37B	0.8080	0.1266	0.6685	0.044*
H37C	0.9227	0.1057	0.7281	0.044*
H38A	1.1718	0.1615	0.7454	0.041*
H38B	1.0926	0.1511	0.8229	0.041*
H39A	1.0282	0.2112	0.8463	0.038*
H39B	1.1809	0.2190	0.7979	0.038*
H40A	0.8977	0.2657	0.7940	0.034*
H40B	0.8339	0.2654	0.7086	0.034*
H40C	1.0138	0.2764	0.7295	0.034*
H44	1.2916	0.0759	0.8462	0.030*
H45	1.3399	0.1122	0.9524	0.031*
H46	1.1378	0.1256	1.0301	0.030*
H48	0.8627	0.1213	1.0618	0.027*
H49	0.6085	0.1000	1.0373	0.030*
H50	0.5475	0.0646	0.9313	0.027*
H52A	0.7556	0.0038	0.9488	0.031*
H52B	0.7587	−0.0387	0.9241	0.031*
H52C	0.6213	−0.0239	0.9748	0.031*
H53A	0.4342	−0.0509	0.8571	0.029*
H53B	0.5977	−0.0593	0.8173	0.029*
H54A	0.4511	−0.0396	0.7146	0.030*
H54B	0.3447	−0.0124	0.7632	0.030*
H55A	0.5991	0.0563	0.6970	0.033*
H55B	0.4168	0.0470	0.7083	0.033*
H55C	0.5096	0.0265	0.6444	0.033*
H57A	0.9865	0.0442	0.6545	0.036*
H57B	0.8263	0.0206	0.6515	0.036*
H57C	0.9724	0.0078	0.6041	0.036*
H58A	0.9891	−0.0568	0.6821	0.031*
H58B	0.8292	−0.0418	0.7175	0.031*
H59A	0.9427	−0.0684	0.8224	0.031*
H59B	1.1199	−0.0610	0.7961	0.031*
H60A	1.2180	−0.0115	0.8974	0.030*
H60B	1.0747	0.0099	0.9335	0.030*
H60C	1.0830	−0.0343	0.9370	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0241 (13)	0.0171 (12)	0.0174 (12)	−0.0017 (10)	−0.0040 (9)	−0.0018 (9)
C2	0.0227 (12)	0.0168 (12)	0.0154 (12)	−0.0024 (9)	−0.0059 (9)	0.0019 (9)
C3	0.0217 (12)	0.0152 (12)	0.0204 (12)	−0.0046 (9)	−0.0040 (10)	−0.0003 (9)
C4	0.0209 (13)	0.0255 (14)	0.0240 (13)	−0.0003 (10)	−0.0049 (10)	−0.0038 (10)
C5	0.0260 (13)	0.0257 (14)	0.0217 (13)	−0.0030 (11)	0.0007 (10)	−0.0046 (10)
C6	0.0313 (14)	0.0207 (13)	0.0191 (13)	−0.0027 (11)	−0.0049 (10)	−0.0012 (9)
C7	0.0257 (13)	0.0162 (12)	0.0183 (12)	−0.0031 (10)	−0.0049 (10)	0.0002 (9)
C8	0.0268 (13)	0.0201 (13)	0.0179 (12)	−0.0007 (10)	−0.0088 (10)	0.0023 (9)
C9	0.0225 (13)	0.0241 (14)	0.0251 (14)	0.0017 (10)	−0.0109 (10)	0.0003 (10)
C10	0.0208 (12)	0.0220 (13)	0.0233 (13)	−0.0006 (10)	−0.0039 (10)	−0.0034 (10)
C11	0.0188 (12)	0.0211 (13)	0.0202 (12)	0.0023 (10)	−0.0027 (9)	−0.0006 (9)
C12	0.0332 (14)	0.0184 (13)	0.0269 (14)	0.0023 (11)	−0.0043 (11)	−0.0003 (10)
C13	0.0428 (16)	0.0271 (15)	0.0219 (14)	0.0011 (12)	−0.0069 (12)	−0.0018 (10)
C14	0.0371 (15)	0.0291 (15)	0.0195 (13)	−0.0006 (12)	−0.0087 (11)	0.0005 (10)
C15	0.0308 (14)	0.0197 (13)	0.0283 (14)	−0.0022 (11)	−0.0036 (11)	0.0046 (10)
C16	0.0201 (12)	0.0200 (13)	0.0208 (12)	0.0019 (10)	−0.0017 (10)	0.0007 (9)
C17	0.0349 (15)	0.0210 (14)	0.0290 (14)	0.0042 (11)	−0.0067 (11)	0.0022 (10)
C18	0.0289 (14)	0.0293 (15)	0.0278 (14)	0.0042 (11)	−0.0092 (11)	−0.0001 (11)
C19	0.0280 (14)	0.0319 (15)	0.0255 (14)	−0.0023 (11)	−0.0128 (11)	−0.0006 (11)
C20	0.0320 (14)	0.0213 (14)	0.0303 (14)	−0.0006 (11)	−0.0063 (11)	−0.0001 (10)
C21	0.0262 (13)	0.0158 (12)	0.0215 (13)	−0.0028 (10)	−0.0078 (10)	−0.0010 (9)
C22	0.0248 (13)	0.0173 (12)	0.0204 (12)	0.0013 (10)	−0.0094 (10)	−0.0026 (9)
C23	0.0284 (13)	0.0214 (13)	0.0194 (12)	−0.0017 (10)	−0.0049 (10)	−0.0020 (10)
C24	0.0268 (14)	0.0352 (16)	0.0299 (15)	0.0009 (12)	−0.0037 (11)	−0.0017 (11)
C25	0.0366 (15)	0.0386 (17)	0.0242 (14)	−0.0084 (13)	0.0009 (11)	−0.0007 (11)
C26	0.0415 (16)	0.0259 (14)	0.0214 (13)	−0.0043 (12)	−0.0074 (11)	0.0030 (10)
C27	0.0318 (14)	0.0194 (13)	0.0172 (12)	−0.0011 (10)	−0.0090 (10)	−0.0060 (9)
C28	0.0355 (15)	0.0201 (13)	0.0241 (13)	0.0029 (11)	−0.0129 (11)	−0.0007 (10)
C29	0.0278 (14)	0.0279 (14)	0.0306 (14)	0.0099 (11)	−0.0120 (11)	−0.0044 (11)
C30	0.0247 (13)	0.0277 (15)	0.0294 (14)	0.0030 (11)	−0.0067 (11)	−0.0036 (11)
C31	0.0228 (13)	0.0215 (13)	0.0248 (13)	0.0011 (10)	−0.0020 (10)	0.0011 (10)
C32	0.0414 (16)	0.0277 (15)	0.0349 (15)	0.0037 (12)	−0.0078 (12)	−0.0060 (11)
C33	0.0422 (16)	0.0404 (17)	0.0194 (13)	0.0016 (13)	−0.0045 (12)	0.0016 (11)
C34	0.0396 (16)	0.0389 (17)	0.0260 (15)	−0.0004 (13)	−0.0085 (12)	0.0094 (11)
C35	0.0373 (16)	0.0247 (15)	0.0402 (16)	−0.0038 (12)	−0.0008 (12)	0.0073 (11)
C36	0.0252 (13)	0.0227 (13)	0.0229 (13)	0.0032 (10)	−0.0023 (10)	−0.0001 (10)
C37	0.0443 (17)	0.0262 (15)	0.0376 (16)	0.0080 (13)	−0.0076 (13)	−0.0013 (12)
C38	0.0332 (15)	0.0364 (16)	0.0330 (15)	0.0072 (12)	−0.0091 (12)	0.0041 (12)
C39	0.0285 (14)	0.0374 (16)	0.0286 (14)	0.0009 (12)	−0.0083 (11)	0.0038 (11)
C40	0.0315 (14)	0.0245 (14)	0.0294 (14)	−0.0017 (11)	−0.0038 (11)	−0.0030 (11)
C41	0.0237 (13)	0.0170 (12)	0.0171 (12)	0.0022 (10)	−0.0077 (10)	0.0005 (9)
C42	0.0218 (12)	0.0136 (12)	0.0194 (12)	0.0027 (9)	−0.0070 (9)	−0.0004 (9)
C43	0.0254 (13)	0.0161 (12)	0.0188 (12)	0.0035 (10)	−0.0053 (10)	0.0015 (9)
C44	0.0231 (13)	0.0244 (14)	0.0283 (14)	0.0008 (10)	−0.0008 (10)	−0.0009 (10)
C45	0.0242 (13)	0.0232 (14)	0.0296 (14)	−0.0014 (10)	−0.0091 (11)	−0.0038 (10)
C46	0.0295 (14)	0.0202 (13)	0.0238 (13)	0.0012 (10)	−0.0083 (11)	−0.0057 (10)
C47	0.0260 (13)	0.0141 (12)	0.0209 (12)	0.0029 (10)	−0.0084 (10)	−0.0001 (9)
C48	0.0302 (14)	0.0175 (12)	0.0190 (12)	0.0029 (10)	−0.0061 (10)	−0.0043 (9)
C49	0.0289 (14)	0.0238 (13)	0.0207 (13)	0.0035 (11)	−0.0030 (10)	−0.0011 (10)
C50	0.0216 (13)	0.0211 (13)	0.0250 (13)	−0.0002 (10)	−0.0061 (10)	0.0001 (10)
C51	0.0183 (12)	0.0198 (13)	0.0163 (12)	0.0021 (10)	−0.0030 (9)	−0.0002 (9)
C52	0.0300 (14)	0.0234 (14)	0.0237 (13)	−0.0023 (11)	−0.0087 (11)	0.0030 (10)
C53	0.0268 (13)	0.0192 (13)	0.0252 (13)	−0.0038 (10)	−0.0049 (10)	−0.0001 (10)
C54	0.0248 (13)	0.0221 (13)	0.0283 (14)	−0.0044 (10)	−0.0067 (10)	−0.0046 (10)
C55	0.0348 (15)	0.0266 (14)	0.0210 (13)	0.0009 (11)	−0.0106 (11)	0.0012 (10)
C56	0.0168 (12)	0.0234 (13)	0.0188 (12)	0.0000 (10)	−0.0030 (9)	0.0008 (9)
C57	0.0372 (15)	0.0317 (15)	0.0196 (13)	0.0041 (12)	−0.0030 (11)	0.0003 (10)
C58	0.0288 (13)	0.0211 (13)	0.0268 (14)	−0.0023 (11)	−0.0022 (11)	−0.0041 (10)
C59	0.0330 (14)	0.0176 (13)	0.0264 (14)	−0.0010 (10)	−0.0027 (11)	−0.0022 (10)
C60	0.0321 (14)	0.0240 (14)	0.0182 (12)	0.0025 (11)	−0.0051 (10)	0.0031 (10)
N1	0.0231 (10)	0.0206 (11)	0.0169 (10)	−0.0012 (8)	−0.0047 (8)	0.0005 (8)
N2	0.0348 (12)	0.0187 (11)	0.0192 (11)	−0.0005 (9)	−0.0086 (9)	−0.0020 (8)
N3	0.0291 (11)	0.0186 (10)	0.0185 (10)	−0.0014 (9)	−0.0057 (8)	0.0027 (8)
N4	0.0207 (10)	0.0193 (11)	0.0192 (10)	−0.0012 (8)	−0.0041 (8)	0.0021 (8)
N5	0.0254 (11)	0.0197 (11)	0.0260 (11)	0.0027 (9)	−0.0094 (9)	0.0006 (8)
N6	0.0238 (11)	0.0212 (11)	0.0234 (11)	−0.0010 (8)	−0.0068 (8)	−0.0002 (8)
N7	0.0251 (11)	0.0214 (11)	0.0241 (11)	0.0002 (9)	−0.0053 (9)	0.0017 (8)
N8	0.0312 (12)	0.0252 (12)	0.0203 (11)	0.0000 (9)	−0.0050 (9)	−0.0002 (8)
N9	0.0361 (13)	0.0258 (12)	0.0247 (12)	−0.0002 (10)	−0.0057 (9)	0.0070 (9)
N10	0.0249 (11)	0.0210 (11)	0.0260 (11)	0.0040 (9)	−0.0055 (9)	−0.0007 (8)
N11	0.0306 (12)	0.0238 (12)	0.0295 (12)	0.0067 (9)	−0.0086 (9)	0.0008 (9)
N12	0.0256 (11)	0.0247 (12)	0.0264 (11)	0.0023 (9)	−0.0060 (9)	0.0012 (9)
N13	0.0220 (10)	0.0188 (11)	0.0201 (10)	−0.0012 (8)	−0.0057 (8)	−0.0023 (8)
N14	0.0246 (11)	0.0196 (11)	0.0183 (10)	−0.0039 (8)	−0.0057 (8)	0.0022 (8)
N15	0.0228 (10)	0.0176 (10)	0.0213 (11)	−0.0014 (8)	−0.0066 (8)	0.0000 (8)
N16	0.0246 (11)	0.0176 (11)	0.0190 (10)	0.0002 (8)	−0.0048 (8)	−0.0006 (8)
N17	0.0267 (11)	0.0203 (11)	0.0194 (10)	0.0003 (9)	−0.0040 (8)	−0.0006 (8)
N18	0.0274 (11)	0.0151 (10)	0.0207 (11)	−0.0015 (8)	−0.0041 (8)	0.0013 (8)

Geometric parameters (Å, º)

C1—C10	1.380 (3)	N17—C58	1.455 (3)
C2—C1	1.449 (3)	N18—C56	1.387 (3)
C2—C3	1.437 (3)	N18—C59	1.463 (3)
C2—C7	1.439 (3)	N18—C60	1.458 (3)
C3—C4	1.385 (3)	C4—H4	0.9500
C5—C4	1.395 (3)	C5—H5	0.9500
C6—C5	1.364 (3)	C6—H6	0.9500
C6—C7	1.415 (3)	C8—H8	0.9500
C7—C8	1.418 (3)	C9—H9	0.9500
C8—C9	1.368 (3)	C10—H10	0.9500
C10—C9	1.400 (3)	C12—H12A	0.9800
C13—C14	1.514 (3)	C12—H12B	0.9800
C19—C18	1.511 (3)	C12—H12C	0.9800
C21—C30	1.379 (3)	C13—H13A	0.9900
C22—C21	1.448 (3)	C13—H13B	0.9900
C22—C23	1.448 (3)	C14—H14A	0.9900
C22—C27	1.434 (3)	C14—H14B	0.9900
C23—C24	1.384 (3)	C15—H15A	0.9800
C25—C24	1.398 (3)	C15—H15B	0.9800
C26—C25	1.356 (3)	C15—H15C	0.9800
C27—C26	1.411 (3)	C17—H17A	0.9800
C27—C28	1.417 (3)	C17—H17B	0.9800
C29—C28	1.355 (3)	C17—H17C	0.9800
C29—C30	1.401 (3)	C18—H18A	0.9900
C33—C34	1.514 (4)	C18—H18B	0.9900
C38—C39	1.517 (3)	C19—H19A	0.9900
C42—C41	1.442 (3)	C19—H19B	0.9900
C42—C47	1.434 (3)	C20—H20A	0.9800
C43—C42	1.448 (3)	C20—H20B	0.9800
C43—C44	1.380 (3)	C20—H20C	0.9800
C43—N16	1.408 (3)	C24—H24	0.9500
C45—C44	1.400 (3)	C25—H25	0.9500
C45—C46	1.360 (3)	C26—H26	0.9500
C47—C46	1.416 (3)	C28—H28	0.9500
C48—C47	1.422 (3)	C29—H29	0.9500
C48—C49	1.362 (3)	C30—H30	0.9500
C50—C41	1.392 (3)	C32—H32A	0.9800
C50—C49	1.398 (3)	C32—H32B	0.9800
C54—C53	1.514 (3)	C32—H32C	0.9800
C58—C59	1.512 (3)	C33—H33A	0.9900
N1—C1	1.397 (3)	C33—H33B	0.9900
N1—C11	1.275 (3)	C34—H34A	0.9900
N2—C11	1.384 (3)	C34—H34B	0.9900
N2—C12	1.446 (3)	C35—H35A	0.9800
N2—C13	1.461 (3)	C35—H35B	0.9800
N3—C11	1.389 (3)	C35—H35C	0.9800
N3—C14	1.457 (3)	C37—H37A	0.9800
N3—C15	1.447 (3)	C37—H37B	0.9800
N4—C3	1.399 (3)	C37—H37C	0.9800
N4—C16	1.283 (3)	C38—H38A	0.9900
N5—C16	1.392 (3)	C38—H38B	0.9900
N5—C17	1.443 (3)	C39—H39A	0.9900
N5—C18	1.470 (3)	C39—H39B	0.9900
N6—C16	1.383 (3)	C40—H40A	0.9800
N6—C19	1.463 (3)	C40—H40B	0.9800
N6—C20	1.452 (3)	C40—H40C	0.9800
N7—C21	1.398 (3)	C44—H44	0.9500
N7—C31	1.278 (3)	C45—H45	0.9500
N8—C31	1.386 (3)	C46—H46	0.9500
N8—C32	1.451 (3)	C48—H48	0.9500
N8—C33	1.459 (3)	C49—H49	0.9500
N9—C31	1.374 (3)	C50—H50	0.9500
N9—C34	1.457 (3)	C52—H52A	0.9800
N9—C35	1.452 (3)	C52—H52B	0.9800
N10—C23	1.396 (3)	C52—H52C	0.9800
N10—C36	1.281 (3)	C53—H53A	0.9900
N11—C36	1.386 (3)	C53—H53B	0.9900
N11—C37	1.458 (3)	C54—H54A	0.9900
N11—C38	1.457 (3)	C54—H54B	0.9900
N12—C36	1.383 (3)	C55—H55A	0.9800
N12—C39	1.466 (3)	C55—H55B	0.9800
N12—C40	1.449 (3)	C55—H55C	0.9800
N13—C41	1.393 (3)	C57—H57A	0.9800
N13—C51	1.279 (3)	C57—H57B	0.9800
N14—C51	1.384 (3)	C57—H57C	0.9800
N14—C52	1.455 (3)	C58—H58A	0.9900
N14—C53	1.458 (3)	C58—H58B	0.9900
N15—C51	1.388 (3)	C59—H59A	0.9900
N15—C54	1.456 (3)	C59—H59B	0.9900
N15—C55	1.448 (3)	C60—H60C	0.9800
N16—C56	1.275 (3)	C60—H60B	0.9800
N17—C56	1.383 (3)	C60—H60A	0.9800
N17—C57	1.449 (3)
C1—C10—C9	122.5 (2)	C25—C24—H24	119.0
C3—C2—C1	125.09 (19)	C25—C26—H26	119.6
C3—C2—C7	117.7 (2)	C26—C25—H25	119.9
C3—C4—C5	122.3 (2)	C27—C26—H26	119.6
C4—C3—C2	119.10 (19)	C27—C28—H28	119.6
C5—C6—C7	120.2 (2)	C28—C29—H29	120.0
C6—C5—C4	120.3 (2)	C29—C28—H28	119.6
C6—C7—C2	120.4 (2)	C29—C30—H30	118.8
C7—C2—C1	117.20 (19)	C30—C29—H29	120.0
C8—C7—C2	120.7 (2)	C33—C34—H34A	111.3
C8—C7—C6	118.9 (2)	C33—C34—H34B	111.3
C8—C9—C10	120.1 (2)	C34—C33—H33A	111.1
C9—C8—C7	120.2 (2)	C34—C33—H33B	111.1
C10—C1—C2	119.3 (2)	C38—C39—H39A	111.4
C10—C1—N1	116.9 (2)	C38—C39—H39B	111.4
C11—N1—C1	127.2 (2)	C39—C38—H38A	111.4
C11—N2—C12	121.36 (18)	C39—C38—H38B	111.4
C11—N2—C13	108.95 (18)	C41—C50—H50	118.9
C11—N3—C14	109.49 (18)	C43—C44—H44	118.9
C11—N3—C15	119.76 (18)	C44—C45—H45	120.0
C12—N2—C13	115.71 (18)	C45—C44—H44	118.9
C15—N3—C14	118.15 (18)	C45—C46—H46	119.8
C16—N4—C3	123.43 (19)	C46—C45—H45	120.0
C16—N5—C17	118.42 (18)	C47—C46—H46	119.8
C16—N5—C18	108.34 (18)	C47—C48—H48	119.8
C16—N6—C19	109.95 (18)	C48—C49—H49	119.8
C16—N6—C20	124.26 (18)	C49—C48—H48	119.8
C17—N5—C18	116.01 (18)	C49—C50—H50	118.9
C20—N6—C19	117.00 (18)	C50—C49—H49	119.8
C21—C22—C23	125.0 (2)	C53—C54—H54A	111.5
C21—C30—C29	122.4 (2)	C53—C54—H54B	111.5
C23—C24—C25	122.0 (2)	C54—C53—H53A	111.3
C24—C23—C22	119.2 (2)	C54—C53—H53B	111.3
C25—C26—C27	120.7 (2)	C58—C59—H59A	111.3
C26—C25—C24	120.3 (2)	C58—C59—H59B	111.3
C26—C27—C22	120.5 (2)	C59—C58—H58A	111.5
C26—C27—C28	119.4 (2)	C59—C58—H58B	111.5
C27—C22—C21	117.7 (2)	N2—C12—H12A	109.5
C27—C22—C23	117.3 (2)	N2—C12—H12B	109.5
C28—C27—C22	120.1 (2)	N2—C12—H12C	109.5
C28—C29—C30	120.1 (2)	N2—C13—H13A	111.2
C29—C28—C27	120.7 (2)	N2—C13—H13B	111.2
C30—C21—C22	118.8 (2)	N3—C14—H14A	111.5
C30—C21—N7	117.0 (2)	N3—C14—H14B	111.5
C31—N7—C21	125.3 (2)	N3—C15—H15A	109.5
C31—N8—C32	120.21 (19)	N3—C15—H15B	109.5
C31—N8—C33	110.01 (19)	N3—C15—H15C	109.5
C31—N9—C34	110.5 (2)	N5—C17—H17A	109.5
C31—N9—C35	120.0 (2)	N5—C17—H17B	109.5
C32—N8—C33	115.34 (19)	N5—C17—H17C	109.5
C35—N9—C34	120.2 (2)	N5—C18—H18A	111.4
C36—N10—C23	123.5 (2)	N5—C18—H18B	111.4
C36—N11—C37	118.74 (19)	N6—C19—H19A	111.4
C36—N11—C38	109.6 (2)	N6—C19—H19B	111.4
C36—N12—C39	109.94 (19)	N6—C20—H20A	109.5
C36—N12—C40	126.04 (19)	N6—C20—H20B	109.5
C38—N11—C37	116.7 (2)	N6—C20—H20C	109.5
C40—N12—C39	116.16 (19)	N8—C32—H32A	109.5
C41—C42—C43	124.76 (19)	N8—C32—H32B	109.5
C41—C50—C49	122.2 (2)	N8—C32—H32C	109.5
C43—C44—C45	122.2 (2)	N8—C33—H33A	111.1
C44—C43—C42	119.4 (2)	N8—C33—H33B	111.1
C44—C43—N16	116.7 (2)	N9—C34—H34A	111.3
C45—C46—C47	120.4 (2)	N9—C34—H34B	111.3
C46—C45—C44	120.1 (2)	N9—C35—H35A	109.5
C46—C47—C42	120.8 (2)	N9—C35—H35B	109.5
C46—C47—C48	119.2 (2)	N9—C35—H35C	109.5
C47—C42—C41	118.2 (2)	N11—C37—H37A	109.5
C47—C42—C43	117.03 (19)	N11—C37—H37B	109.5
C48—C47—C42	120.1 (2)	N11—C37—H37C	109.5
C48—C49—C50	120.4 (2)	N11—C38—H38A	111.4
C49—C48—C47	120.4 (2)	N11—C38—H38B	111.4
C50—C41—C42	118.7 (2)	N12—C39—H39A	111.4
C51—N13—C41	125.44 (19)	N12—C39—H39B	111.4
C51—N14—C52	123.77 (18)	N12—C40—H40A	109.5
C51—N14—C53	109.19 (17)	N12—C40—H40B	109.5
C51—N15—C54	109.54 (18)	N12—C40—H40C	109.5
C51—N15—C55	118.42 (18)	N14—C52—H52A	109.5
C52—N14—C53	116.11 (18)	N14—C52—H52B	109.5
C55—N15—C54	116.99 (18)	N14—C52—H52C	109.5
C56—N16—C43	125.91 (19)	N14—C53—H53A	111.3
C56—N17—C57	119.63 (19)	N14—C53—H53B	111.3
C56—N17—C58	109.56 (18)	N15—C54—H54A	111.5
C56—N18—C59	109.07 (18)	N15—C54—H54B	111.5
C56—N18—C60	121.15 (18)	N15—C55—H55A	109.5
C57—N17—C58	118.75 (18)	N15—C55—H55B	109.5
C59—N18—C60	116.72 (17)	N15—C55—H55C	109.5
N1—C1—C2	123.32 (19)	N17—C57—H57A	109.5
N1—C11—N2	131.7 (2)	N17—C57—H57B	109.5
N1—C11—N3	120.2 (2)	N17—C57—H57C	109.5
N2—C11—N3	108.08 (18)	N17—C58—H58A	111.5
N2—C13—C14	102.76 (18)	N17—C58—H58B	111.5
N3—C14—C13	101.26 (18)	N18—C59—H59A	111.3
N4—C3—C2	121.6 (2)	N18—C59—H59B	111.3
N4—C3—C4	118.9 (2)	N18—C60—H60A	109.5
N4—C16—N5	120.6 (2)	N18—C60—H60C	109.5
N4—C16—N6	131.4 (2)	N18—C60—H60B	109.5
N5—C16—N6	107.97 (18)	H12A—C12—H12B	109.5
N5—C18—C19	102.05 (18)	H12A—C12—H12C	109.5
N6—C19—C18	101.82 (18)	H12B—C12—H12C	109.5
N7—C21—C22	123.9 (2)	H13A—C13—H13B	109.1
N7—C31—N8	130.3 (2)	H14A—C14—H14B	109.3
N7—C31—N9	121.6 (2)	H15A—C15—H15B	109.5
N8—C31—N9	108.15 (19)	H15A—C15—H15C	109.5
N8—C33—C34	103.30 (19)	H15B—C15—H15C	109.5
N9—C34—C33	102.52 (19)	H17B—C17—H17A	109.5
N10—C23—C22	121.7 (2)	H17C—C17—H17A	109.5
N10—C23—C24	118.9 (2)	H17C—C17—H17B	109.5
N11—C38—C39	101.90 (19)	H18A—C18—H18B	109.2
N12—C39—C38	101.95 (19)	H19A—C19—H19B	109.3
N13—C41—C42	121.3 (2)	H20B—C20—H20A	109.5
N13—C41—C50	119.5 (2)	H20C—C20—H20A	109.5
N13—C51—N14	131.6 (2)	H20C—C20—H20B	109.5
N13—C51—N15	120.6 (2)	H32A—C32—H32B	109.5
N14—C51—N15	107.82 (19)	H32A—C32—H32C	109.5
N14—C53—C54	102.21 (18)	H32B—C32—H32C	109.5
N15—C54—C53	101.45 (17)	H33A—C33—H33B	109.1
N16—C43—C42	123.64 (19)	H34A—C34—H34B	109.2
N16—C56—N17	120.9 (2)	H35B—C35—H35A	109.5
N16—C56—N18	131.3 (2)	H35C—C35—H35A	109.5
N17—C56—N18	107.87 (19)	H35C—C35—H35B	109.5
N17—C58—C59	101.44 (17)	H37A—C37—H37B	109.5
N18—C59—C58	102.27 (18)	H37A—C37—H37C	109.5
C1—C10—H10	118.8	H37B—C37—H37C	109.5
C3—C4—H4	118.9	H38A—C38—H38B	109.3
C4—C5—H5	119.9	H39A—C39—H39B	109.2
C5—C4—H4	118.9	H40A—C40—H40B	109.5
C5—C6—H6	119.9	H40A—C40—H40C	109.5
C6—C5—H5	119.9	H40B—C40—H40C	109.5
C7—C6—H6	119.9	H52A—C52—H52B	109.5
C7—C8—H8	119.9	H52A—C52—H52C	109.5
C8—C9—H9	120.0	H52B—C52—H52C	109.5
C9—C8—H8	119.9	H53A—C53—H53B	109.2
C9—C10—H10	118.8	H54A—C54—H54B	109.3
C10—C9—H9	120.0	H55A—C55—H55B	109.5
C13—C14—H14A	111.5	H55A—C55—H55C	109.5
C13—C14—H14B	111.5	H55B—C55—H55C	109.5
C14—C13—H13A	111.2	H57A—C57—H57B	109.5
C14—C13—H13B	111.2	H57A—C57—H57C	109.5
C18—C19—H19A	111.4	H57B—C57—H57C	109.5
C18—C19—H19B	111.4	H58A—C58—H58B	109.3
C19—C18—H18A	111.4	H59A—C59—H59B	109.2
C19—C18—H18B	111.4	H60B—C60—H60A	109.5
C21—C30—H30	118.8	H60C—C60—H60A	109.5
C23—C24—H24	119.0	H60C—C60—H60B	109.5
C24—C25—H25	119.9
C1—C2—C3—C4	−179.5 (2)	C33—N8—C31—N7	175.2 (2)
C1—C2—C3—N4	7.8 (3)	C33—N8—C31—N9	−4.8 (3)
C1—C2—C7—C6	179.38 (19)	C34—N9—C31—N7	168.9 (2)
C1—C2—C7—C8	−0.7 (3)	C34—N9—C31—N8	−11.0 (3)
C1—C10—C9—C8	0.0 (3)	C35—N9—C31—N7	22.2 (4)
C1—N1—C11—N2	1.1 (4)	C35—N9—C31—N8	−157.8 (2)
C1—N1—C11—N3	−178.3 (2)	C35—N9—C34—C33	168.0 (2)
C2—C1—C10—C9	−1.3 (3)	C36—N10—C23—C22	−128.1 (2)
C2—C3—C4—C5	0.8 (3)	C36—N10—C23—C24	57.9 (3)
C2—C7—C8—C9	−0.5 (3)	C36—N11—C38—C39	26.9 (3)
C3—C2—C1—C10	−178.8 (2)	C36—N12—C39—C38	22.5 (3)
C3—C2—C1—N1	−7.3 (3)	C37—N11—C38—C39	165.5 (2)
C3—C2—C7—C6	−0.3 (3)	C37—N11—C36—N10	29.7 (3)
C3—C2—C7—C8	179.6 (2)	C37—N11—C36—N12	−151.3 (2)
C3—N4—C16—N5	−165.0 (2)	C38—N11—C36—N10	167.4 (2)
C3—N4—C16—N6	14.8 (4)	C38—N11—C36—N12	−13.6 (3)
C5—C6—C7—C2	−0.5 (3)	C39—N12—C36—N10	172.4 (2)
C5—C6—C7—C8	179.7 (2)	C39—N12—C36—N11	−6.5 (3)
C6—C5—C4—C3	−1.6 (3)	C40—N12—C36—N10	24.8 (4)
C6—C7—C8—C9	179.4 (2)	C40—N12—C36—N11	−154.0 (2)
C7—C2—C1—C10	1.6 (3)	C40—N12—C39—C38	173.6 (2)
C7—C2—C1—N1	173.1 (2)	C41—C42—C47—C46	−179.6 (2)
C7—C2—C3—C4	0.1 (3)	C41—C42—C47—C48	1.1 (3)
C7—C2—C3—N4	−172.56 (19)	C41—C50—C49—C48	0.0 (4)
C7—C6—C5—C4	1.4 (3)	C41—N13—C51—N14	−15.8 (4)
C7—C8—C9—C10	0.9 (3)	C41—N13—C51—N15	165.7 (2)
C11—N1—C1—C2	78.7 (3)	C42—C43—C44—C45	1.5 (3)
C11—N1—C1—C10	−109.6 (3)	C42—C43—N16—C56	−76.3 (3)
C11—N2—C13—C14	24.1 (2)	C42—C47—C46—C45	0.2 (3)
C11—N3—C14—C13	26.8 (2)	C43—C42—C41—C50	177.5 (2)
C12—N2—C11—N1	34.4 (4)	C43—C42—C41—N13	−9.9 (3)
C12—N2—C11—N3	−146.1 (2)	C43—C42—C47—C46	1.3 (3)
C12—N2—C13—C14	165.0 (2)	C43—C42—C47—C48	−178.03 (19)
C13—N2—C11—N1	172.7 (2)	C43—N16—C56—N17	178.4 (2)
C13—N2—C11—N3	−7.8 (2)	C43—N16—C56—N18	−2.7 (4)
C14—N3—C11—N1	166.7 (2)	C44—C43—C42—C41	178.8 (2)
C14—N3—C11—N2	−12.8 (3)	C44—C43—C42—C47	−2.1 (3)
C15—N3—C11—N1	25.5 (3)	C44—C43—N16—C56	109.6 (3)
C15—N3—C11—N2	−153.99 (19)	C44—C45—C46—C47	−0.9 (4)
C15—N3—C14—C13	168.7 (2)	C46—C45—C44—C43	0.1 (4)
C16—N4—C3—C2	−131.0 (2)	C47—C42—C41—C50	−1.6 (3)
C16—N4—C3—C4	56.3 (3)	C47—C42—C41—N13	171.01 (19)
C16—N5—C18—C19	28.3 (2)	C47—C48—C49—C50	−0.5 (3)
C16—N6—C19—C18	23.4 (2)	C48—C47—C46—C45	179.5 (2)
C17—N5—C16—N4	30.5 (3)	C49—C48—C47—C42	−0.1 (3)
C17—N5—C16—N6	−149.3 (2)	C49—C48—C47—C46	−179.4 (2)
C17—N5—C18—C19	164.35 (19)	C49—C50—C41—C42	1.1 (3)
C18—N5—C16—N4	165.3 (2)	C49—C50—C41—N13	−171.6 (2)
C18—N5—C16—N6	−14.5 (2)	C51—N13—C41—C42	135.1 (2)
C19—N6—C16—N4	173.9 (2)	C51—N13—C41—C50	−52.4 (3)
C19—N6—C16—N5	−6.3 (3)	C51—N14—C53—C54	−25.6 (2)
C20—N6—C16—N4	27.6 (4)	C51—N15—C54—C53	−26.4 (2)
C20—N6—C16—N5	−152.6 (2)	C52—N14—C53—C54	−171.26 (19)
C20—N6—C19—C18	172.42 (19)	C55—N15—C54—C53	−164.77 (19)
C21—C22—C23—C24	179.4 (2)	C56—N17—C58—C59	−27.5 (2)
C21—C22—C23—N10	5.5 (3)	C56—N18—C59—C58	−24.3 (2)
C21—C22—C27—C26	179.1 (2)	C57—N17—C58—C59	−170.02 (19)
C21—C22—C27—C28	0.2 (3)	C59—N18—C56—N16	−171.2 (2)
C21—N7—C31—N8	6.8 (4)	C59—N18—C56—N17	7.8 (2)
C21—N7—C31—N9	−173.1 (2)	C60—N18—C56—N16	−31.3 (4)
C22—C21—C30—C29	−4.7 (3)	C60—N18—C56—N17	147.7 (2)
C22—C23—C24—C25	2.1 (4)	C60—N18—C59—C58	−166.15 (19)
C22—C27—C26—C25	0.8 (4)	N1—C1—C10—C9	−173.4 (2)
C22—C27—C28—C29	−2.3 (3)	N2—C13—C14—N3	−29.7 (2)
C23—C22—C21—C30	−176.5 (2)	N4—C3—C4—C5	173.7 (2)
C23—C22—C21—N7	−2.8 (3)	N6—C19—C18—N5	−30.1 (2)
C23—C22—C27—C26	−1.2 (3)	N7—C21—C30—C29	−178.8 (2)
C23—C22—C27—C28	179.9 (2)	N8—C33—C34—N9	−22.6 (3)
C23—N10—C36—N11	−167.0 (2)	N10—C23—C24—C25	176.2 (2)
C23—N10—C36—N12	14.2 (4)	N11—C38—C39—N12	−28.7 (2)
C26—C25—C24—C23	−2.5 (4)	N13—C51—N14—C52	−26.4 (4)
C26—C27—C28—C29	178.8 (2)	N13—C51—N14—C53	−168.9 (2)
C27—C22—C21—C30	3.2 (3)	N13—C51—N15—C54	−169.8 (2)
C27—C22—C21—N7	176.9 (2)	N13—C51—N15—C55	−32.1 (3)
C27—C22—C23—C24	−0.2 (3)	N14—C51—N15—C54	11.3 (2)
C27—C22—C23—N10	−174.2 (2)	N14—C51—N15—C55	149.0 (2)
C27—C26—C25—C24	1.0 (4)	N15—C51—N14—C52	152.3 (2)
C28—C27—C26—C25	179.8 (2)	N15—C51—N14—C53	9.8 (2)
C28—C29—C30—C21	2.7 (4)	N15—C54—C53—N14	30.3 (2)
C30—C29—C28—C27	0.9 (4)	N16—C43—C42—C41	4.8 (3)
C31—N7—C21—C22	72.3 (3)	N16—C43—C42—C47	−176.1 (2)
C31—N7—C21—C30	−113.9 (3)	N16—C43—C44—C45	175.9 (2)
C31—N8—C33—C34	17.6 (3)	N16—C56—N17—C57	−25.5 (3)
C31—N9—C34—C33	21.3 (3)	N16—C56—N17—C58	−167.6 (2)
C32—N8—C31—N7	37.6 (4)	N17—C58—C59—N18	30.1 (2)
C32—N8—C31—N9	−142.5 (2)	N18—C56—N17—C57	155.4 (2)
C32—N8—C33—C34	157.5 (2)	N18—C56—N17—C58	13.2 (2)