N,N,N′,N′-Tetrakis(2-pyridinio­methyl)-1,3-di­amino­propane tetraperchlorate monohydrate

The cation of the title compound, H₄tptn⁴⁺·4ClO₄⁻·H₂O, where H₄tptn⁴⁺ is N,N,N′,N′-tetrakis(2-pyridinio­methyl)-1,3-di­amino­propane (C₂₇H₃₄N₆⁴⁺), contains an intramolecular N—H...N hydrogen bond, and the average ring angle at the N atoms in the pyridinium rings is 123.6 (1)°. Intermolecular N—H...O and O—H...O hydrogen bonds are also found in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.066
• wR factor = 0.183
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

N,N,N',N'-Tetrakis(2-pyridiniomethyl)-1,3-diaminopropane tetraperchlorate hydrate

Crystal data

C27H34N6^4+·4ClO4^−·H2O	Z = 2
Mr = 858.42	F(000) = 888
Triclinic, P1	Dx = 1.577 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.6648 (6) Å	Cell parameters from 8505 reflections
b = 12.3882 (6) Å	θ = 2.4–27.9°
c = 12.5333 (6) Å	µ = 0.41 mm^−1
α = 92.168 (1)°	T = 173 K
β = 91.050 (1)°	Plate, colourless
γ = 92.252 (1)°	0.50 × 0.40 × 0.25 mm
V = 1808.09 (15) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	8519 independent reflections
Radiation source: fine-focus sealed tube	7487 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8.366 pixels mm^-1	θmax = 27.9°, θmin = 1.6°
φ and ω scans	h = −15→13
Absorption correction: multi-scan (SADABS; Scheldrick, 1996)	k = −16→15
Tmin = 0.821, Tmax = 0.904	l = −16→16
13190 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.183	w = 1/[σ^2(Fo^2) + (0.0956P)^2 + 2.858P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
8519 reflections	Δρmax = 1.25 e Å^−3
512 parameters	Δρmin = −1.19 e Å^−3
0 restraints	Extinction correction: SHELXTL-NT, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (10)

Special details

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.4974 (0.0104) x - 9.0912 (0.0099) y + 3.8244 (0.0144) z = 3.9411 (0.0113)

* -0.0021 (0.0019) N6 * -0.0068 (0.0018) C23 * 0.0095 (0.0020) C24 * -0.0034 (0.0021) C25 * -0.0054 (0.0021) C26 * 0.0083 (0.0021) C27

Rms deviation of fitted atoms = 0.0065

2.0958 (0.0146) x - 8.0267 (0.0125) y + 9.6089 (0.0106) z = 3.2947 (0.0080)

Angle to previous plane (with approximate e.s.d.) = 38.14 (0.12)

* 0.0090 (0.0020) N5 * 0.0018 (0.0019) C17 * -0.0101 (0.0021) C18 * 0.0077 (0.0024) C19 * 0.0028 (0.0025) C20 * -0.0112 (0.0023) C21

Rms deviation of fitted atoms = 0.0080

4.3281 (0.0123) x - 6.5188 (0.0124) y - 9.5383 (0.0095) z = 1.0154 (0.0100)

Angle to previous plane (with approximate e.s.d.) = 79.47 (0.08)

* -0.0021 (0.0018) N4 * 0.0023 (0.0018) C11 * 0.0013 (0.0020) C12 * -0.0050 (0.0021) C13 * 0.0052 (0.0021) C14 * -0.0017 (0.0020) C15

Rms deviation of fitted atoms = 0.0033

3.0708 (0.0158) x - 4.8544 (0.0164) y - 10.9697 (0.0084) z = 0.2415 (0.0054)

Angle to previous plane (with approximate e.s.d.) = 11.62 (0.17)

* 0.0012 (0.0019) N3 * 0.0095 (0.0021) C5 * -0.0108 (0.0027) C6 * 0.0017 (0.0028) C7 * 0.0089 (0.0025) C8 * -0.0105 (0.0021) C9

Rms deviation of fitted atoms = 0.0082

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
N1	0.40662 (19)	0.20289 (17)	0.02173 (16)	0.0225 (4)
N2	0.37651 (19)	0.21089 (18)	0.42106 (16)	0.0237 (4)
N3	0.2165 (2)	0.27265 (19)	−0.08218 (18)	0.0275 (5)
N4	0.6085 (2)	0.31537 (19)	−0.04565 (18)	0.0277 (5)
N5	0.1549 (2)	0.1608 (2)	0.4444 (2)	0.0311 (5)
N6	0.5972 (2)	0.2981 (2)	0.56764 (18)	0.0286 (5)
C1	0.3905 (2)	0.2653 (2)	0.12303 (19)	0.0233 (5)
C2	0.3988 (3)	0.2012 (2)	0.2244 (2)	0.0334 (6)
C3	0.3783 (2)	0.2731 (2)	0.32284 (19)	0.0246 (5)
C4	0.3130 (2)	0.1234 (2)	−0.0026 (2)	0.0282 (5)
C5	0.2069 (2)	0.1743 (2)	−0.0421 (2)	0.0295 (5)
C6	0.1004 (3)	0.1214 (3)	−0.0467 (3)	0.0457 (8)
C7	0.0090 (3)	0.1693 (3)	−0.0946 (3)	0.0529 (9)
C8	0.0233 (3)	0.2705 (3)	−0.1360 (3)	0.0426 (7)
C9	0.1287 (3)	0.3223 (3)	−0.1276 (2)	0.0347 (6)
C10	0.5167 (2)	0.1504 (2)	0.0177 (2)	0.0256 (5)
C11	0.6172 (2)	0.2300 (2)	0.01619 (19)	0.0247 (5)
C12	0.7192 (2)	0.2174 (2)	0.0712 (2)	0.0314 (6)
C13	0.8090 (3)	0.2923 (3)	0.0614 (3)	0.0375 (6)
C14	0.7972 (3)	0.3787 (3)	−0.0041 (3)	0.0372 (6)
C15	0.6941 (3)	0.3891 (2)	−0.0573 (2)	0.0329 (6)
C16	0.3213 (2)	0.2702 (2)	0.5074 (2)	0.0273 (5)
C17	0.1938 (2)	0.2452 (2)	0.5057 (2)	0.0268 (5)
C18	0.1168 (3)	0.3006 (3)	0.5675 (2)	0.0352 (6)
C19	0.0023 (3)	0.2654 (3)	0.5649 (3)	0.0440 (8)
C20	−0.0343 (3)	0.1777 (3)	0.4991 (3)	0.0471 (8)
C21	0.0438 (3)	0.1263 (3)	0.4376 (3)	0.0431 (7)
C22	0.4858 (2)	0.1646 (2)	0.4520 (2)	0.0259 (5)
C23	0.5839 (2)	0.2468 (2)	0.4706 (2)	0.0255 (5)
C24	0.6603 (2)	0.2752 (2)	0.3928 (2)	0.0314 (6)
C25	0.7452 (3)	0.3553 (3)	0.4135 (2)	0.0368 (6)
C26	0.7547 (3)	0.4057 (3)	0.5140 (3)	0.0359 (6)
C27	0.6794 (2)	0.3745 (3)	0.5909 (2)	0.0340 (6)
H3N	0.283 (3)	0.307 (3)	−0.083 (3)	0.040 (10)*
H4N	0.544 (4)	0.323 (3)	−0.081 (3)	0.041 (10)*
H5N	0.203 (4)	0.129 (3)	0.416 (3)	0.039 (10)*
H6N	0.550 (3)	0.272 (3)	0.617 (3)	0.037 (9)*
H1A	0.3141	0.2974	0.1201	0.028*
H1B	0.4488	0.3256	0.1282	0.028*
H2A	0.3411	0.1403	0.2205	0.040*
H2B	0.4758	0.1708	0.2300	0.040*
H3A	0.4398	0.3305	0.3297	0.030*
H3B	0.3042	0.3083	0.3141	0.030*
H4A	0.2950	0.0838	0.0625	0.034*
H4B	0.3382	0.0704	−0.0576	0.034*
H6	0.0902	0.0524	−0.0169	0.055*
H7	−0.0641	0.1325	−0.0991	0.063*
H8	−0.0391	0.3035	−0.1698	0.051*
H9	0.1400	0.3929	−0.1538	0.042*
H10A	0.5177	0.1023	−0.0471	0.031*
H10B	0.5246	0.1051	0.0806	0.031*
H12	0.7276	0.1576	0.1155	0.038*
H13	0.8790	0.2845	0.0997	0.045*
H14	0.8589	0.4298	−0.0122	0.045*
H15	0.6837	0.4484	−0.1020	0.040*
H16A	0.3360	0.3487	0.4999	0.033*
H16B	0.3546	0.2503	0.5768	0.033*
H18	0.1418	0.3618	0.6110	0.042*
H19	−0.0512	0.3015	0.6084	0.053*
H20	−0.1127	0.1537	0.4968	0.057*
H21	0.0204	0.0671	0.3908	0.052*
H22A	0.5072	0.1119	0.3952	0.031*
H22B	0.4744	0.1247	0.5181	0.031*
H24	0.6547	0.2396	0.3243	0.038*
H25	0.7965	0.3755	0.3590	0.044*
H26	0.8123	0.4608	0.5294	0.043*
H27	0.6855	0.4070	0.6607	0.041*
O1	0.4856 (2)	0.21659 (18)	0.74620 (16)	0.0314 (4)
H101	0.520 (4)	0.165 (4)	0.750 (4)	0.057 (13)*
H102	0.422 (4)	0.204 (3)	0.748 (3)	0.039 (11)*
Cl1	0.40441 (5)	0.47317 (5)	0.79135 (5)	0.02524 (16)
Cl2	0.26320 (6)	0.01407 (5)	0.69972 (5)	0.03152 (17)
Cl3	0.25709 (6)	0.91307 (6)	0.26587 (6)	0.03417 (18)
Cl4	0.06659 (6)	0.43105 (7)	0.23417 (6)	0.0398 (2)
O11	0.40262 (18)	0.42509 (16)	0.89601 (16)	0.0326 (4)
O12	0.3695 (2)	0.58222 (16)	0.80275 (17)	0.0358 (5)
O21	0.2543 (2)	0.12858 (18)	0.72360 (18)	0.0390 (5)
O14	0.3273 (2)	0.41089 (19)	0.72085 (18)	0.0421 (5)
O13	0.5195 (2)	0.47124 (19)	0.7529 (2)	0.0438 (5)
O23	0.3638 (2)	−0.0223 (2)	0.75433 (19)	0.0448 (6)
O22	0.2762 (3)	−0.0046 (3)	0.5877 (2)	0.0670 (9)
O24	0.1657 (3)	−0.0449 (3)	0.7391 (3)	0.0698 (9)
O31	0.2141 (3)	0.8049 (2)	0.2723 (4)	0.0904 (13)
O34	0.3340 (7)	0.9377 (3)	0.3485 (4)	0.157 (3)
O33	0.3170 (6)	0.9211 (3)	0.1752 (3)	0.153 (3)
O42	−0.0387 (5)	0.4733 (5)	0.2552 (6)	0.151 (3)
O43	0.0608 (6)	0.4127 (6)	0.1248 (4)	0.172 (3)
O32	0.1726 (3)	0.9901 (3)	0.2667 (6)	0.149 (3)
O41	0.1612 (5)	0.4995 (7)	0.2472 (4)	0.173 (3)
O44	0.0727 (6)	0.3407 (7)	0.2879 (8)	0.225 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0272 (10)	0.0212 (10)	0.0189 (9)	−0.0002 (8)	−0.0003 (8)	−0.0004 (7)
N2	0.0265 (10)	0.0276 (11)	0.0173 (9)	0.0020 (8)	0.0007 (8)	0.0013 (8)
N3	0.0268 (11)	0.0305 (12)	0.0251 (11)	−0.0001 (9)	−0.0002 (8)	0.0008 (8)
N4	0.0279 (11)	0.0289 (11)	0.0262 (11)	−0.0009 (9)	−0.0001 (9)	0.0033 (8)
N5	0.0301 (12)	0.0297 (12)	0.0335 (12)	−0.0006 (10)	−0.0014 (10)	0.0029 (9)
N6	0.0241 (10)	0.0376 (13)	0.0241 (11)	0.0003 (9)	0.0010 (8)	0.0005 (9)
C1	0.0287 (12)	0.0224 (11)	0.0189 (11)	0.0009 (9)	0.0001 (9)	−0.0001 (8)
C2	0.0532 (17)	0.0296 (13)	0.0181 (12)	0.0094 (12)	0.0018 (11)	0.0019 (10)
C3	0.0287 (12)	0.0246 (12)	0.0209 (11)	0.0043 (9)	−0.0003 (9)	0.0015 (9)
C4	0.0340 (14)	0.0240 (12)	0.0260 (12)	−0.0045 (10)	−0.0047 (10)	0.0027 (9)
C5	0.0314 (13)	0.0327 (14)	0.0243 (12)	−0.0017 (11)	0.0011 (10)	0.0020 (10)
C6	0.0356 (16)	0.0456 (19)	0.056 (2)	−0.0089 (14)	0.0027 (14)	0.0125 (15)
C7	0.0290 (16)	0.063 (2)	0.067 (2)	−0.0072 (15)	−0.0011 (15)	0.0106 (18)
C8	0.0284 (14)	0.059 (2)	0.0412 (17)	0.0078 (14)	−0.0005 (12)	0.0042 (14)
C9	0.0341 (14)	0.0391 (16)	0.0315 (14)	0.0085 (12)	0.0031 (11)	0.0034 (11)
C10	0.0312 (13)	0.0222 (11)	0.0236 (12)	0.0022 (10)	0.0011 (9)	0.0002 (9)
C11	0.0274 (12)	0.0251 (12)	0.0218 (11)	0.0029 (9)	0.0024 (9)	−0.0011 (9)
C12	0.0329 (14)	0.0317 (14)	0.0297 (13)	0.0074 (11)	−0.0035 (11)	−0.0018 (10)
C13	0.0289 (14)	0.0432 (17)	0.0396 (16)	0.0039 (12)	−0.0046 (11)	−0.0078 (13)
C14	0.0296 (14)	0.0391 (16)	0.0418 (16)	−0.0053 (12)	0.0062 (12)	−0.0076 (12)
C15	0.0360 (14)	0.0320 (14)	0.0307 (14)	−0.0035 (11)	0.0038 (11)	0.0031 (11)
C16	0.0255 (12)	0.0355 (14)	0.0204 (11)	−0.0016 (10)	0.0011 (9)	−0.0025 (10)
C17	0.0259 (12)	0.0323 (13)	0.0224 (12)	0.0013 (10)	−0.0018 (9)	0.0061 (10)
C18	0.0304 (14)	0.0467 (17)	0.0287 (14)	0.0061 (12)	−0.0018 (11)	0.0010 (12)
C19	0.0286 (15)	0.062 (2)	0.0427 (17)	0.0100 (14)	0.0026 (12)	0.0078 (15)
C20	0.0267 (14)	0.055 (2)	0.061 (2)	−0.0028 (14)	−0.0026 (14)	0.0151 (17)
C21	0.0357 (16)	0.0374 (16)	0.055 (2)	−0.0079 (13)	−0.0098 (14)	0.0047 (14)
C22	0.0282 (12)	0.0269 (12)	0.0228 (11)	0.0029 (10)	−0.0012 (9)	0.0031 (9)
C23	0.0266 (12)	0.0275 (12)	0.0228 (12)	0.0071 (10)	−0.0012 (9)	0.0033 (9)
C24	0.0329 (14)	0.0379 (15)	0.0240 (12)	0.0039 (11)	0.0034 (10)	0.0035 (10)
C25	0.0314 (14)	0.0461 (17)	0.0337 (15)	0.0008 (12)	0.0048 (11)	0.0123 (12)
C26	0.0286 (14)	0.0366 (15)	0.0425 (16)	−0.0019 (11)	−0.0024 (11)	0.0054 (12)
C27	0.0286 (13)	0.0405 (16)	0.0323 (14)	0.0009 (11)	−0.0031 (11)	−0.0053 (11)
O1	0.0314 (11)	0.0313 (11)	0.0317 (10)	0.0021 (9)	0.0015 (8)	0.0030 (8)
Cl1	0.0301 (3)	0.0202 (3)	0.0253 (3)	0.0010 (2)	0.0011 (2)	−0.0005 (2)
Cl2	0.0335 (3)	0.0291 (3)	0.0319 (3)	0.0009 (3)	−0.0035 (2)	0.0015 (2)
Cl3	0.0302 (3)	0.0284 (3)	0.0435 (4)	−0.0001 (3)	0.0065 (3)	−0.0059 (3)
Cl4	0.0318 (4)	0.0434 (4)	0.0441 (4)	−0.0049 (3)	−0.0069 (3)	0.0090 (3)
O11	0.0381 (11)	0.0305 (10)	0.0293 (10)	−0.0007 (8)	−0.0021 (8)	0.0073 (8)
O13	0.0386 (12)	0.0386 (12)	0.0553 (14)	0.0047 (9)	0.0174 (10)	0.0054 (10)
O12	0.0505 (13)	0.0233 (10)	0.0342 (10)	0.0104 (9)	0.0007 (9)	−0.0001 (8)
O14	0.0498 (13)	0.0410 (12)	0.0339 (11)	−0.0050 (10)	−0.0074 (9)	−0.0093 (9)
O21	0.0418 (12)	0.0300 (11)	0.0459 (12)	0.0075 (9)	0.0039 (9)	0.0028 (9)
O22	0.110 (3)	0.0619 (18)	0.0301 (13)	0.0273 (18)	−0.0094 (14)	−0.0031 (11)
O23	0.0500 (14)	0.0407 (12)	0.0445 (13)	0.0157 (10)	−0.0098 (10)	0.0026 (10)
O24	0.0445 (15)	0.0543 (17)	0.110 (3)	−0.0133 (13)	0.0057 (16)	0.0136 (17)
O31	0.0486 (17)	0.0366 (15)	0.185 (4)	−0.0123 (13)	0.000 (2)	0.002 (2)
O32	0.0435 (19)	0.048 (2)	0.357 (9)	0.0187 (16)	0.024 (3)	−0.020 (3)
O33	0.324 (8)	0.056 (2)	0.090 (3)	0.067 (3)	0.132 (4)	0.031 (2)
O34	0.292 (8)	0.054 (2)	0.118 (4)	−0.023 (3)	−0.130 (5)	−0.004 (2)
O41	0.139 (4)	0.287 (8)	0.078 (3)	−0.164 (5)	−0.005 (3)	−0.011 (4)
O42	0.111 (4)	0.115 (4)	0.239 (7)	0.062 (3)	0.086 (4)	0.075 (4)
O43	0.193 (6)	0.235 (7)	0.073 (3)	−0.150 (6)	0.001 (3)	−0.018 (4)
O44	0.166 (6)	0.212 (7)	0.323 (10)	0.084 (6)	0.081 (6)	0.224 (8)

Geometric parameters (Å, º)

N1—C4	1.461 (3)	C12—C13	1.382 (4)
N1—C10	1.463 (3)	C12—H12	0.9500
N1—C1	1.480 (3)	C16—H16A	0.9900
N2—C16	1.459 (3)	C16—H16B	0.9900
N2—C22	1.469 (3)	C27—C26	1.372 (4)
N2—C3	1.477 (3)	C27—H27	0.9500
N4—C15	1.341 (4)	C26—C25	1.386 (5)
N4—C11	1.341 (3)	C26—H26	0.9500
N4—H4N	0.87 (4)	C9—C8	1.365 (5)
C1—C2	1.526 (3)	C9—H9	0.9500
C1—H1A	0.9900	C14—C13	1.382 (5)
C1—H1B	0.9900	C14—H14	0.9500
C3—C2	1.522 (4)	C18—C19	1.387 (4)
C3—H3A	0.9900	C18—H18	0.9500
C3—H3B	0.9900	C13—H13	0.9500
N6—C27	1.341 (4)	C19—C20	1.389 (6)
N6—C23	1.354 (3)	C19—H19	0.9500
N6—H6N	0.90 (4)	C8—C7	1.381 (5)
N5—C17	1.334 (4)	C8—H8	0.9500
N5—C21	1.348 (4)	C21—C20	1.365 (5)
N5—H5N	0.78 (4)	C21—H21	0.9500
N3—C5	1.336 (4)	C6—C7	1.379 (5)
N3—C9	1.344 (4)	C6—H6	0.9500
N3—H3N	0.88 (4)	C25—H25	0.9500
C4—C5	1.496 (4)	C20—H20	0.9500
C4—H4A	0.9900	C7—H7	0.9500
C4—H4B	0.9900	Cl1—O12	1.429 (2)
C22—C23	1.510 (4)	Cl1—O14	1.431 (2)
C22—H22A	0.9900	Cl1—O13	1.435 (2)
C22—H22B	0.9900	Cl1—O11	1.461 (2)
C10—C11	1.502 (4)	Cl2—O22	1.426 (3)
C10—H10A	0.9900	Cl2—O24	1.433 (3)
C10—H10B	0.9900	Cl2—O23	1.444 (2)
C5—C6	1.381 (4)	Cl2—O21	1.447 (2)
C17—C18	1.382 (4)	Cl3—O33	1.349 (3)
C17—C16	1.507 (4)	Cl3—O34	1.376 (4)
C24—C23	1.379 (4)	Cl3—O32	1.398 (3)
C24—C25	1.389 (4)	Cl3—O31	1.418 (3)
C24—H24	0.9500	Cl4—O44	1.332 (5)
C11—C12	1.381 (4)	Cl4—O41	1.369 (4)
C2—H2A	0.9900	Cl4—O42	1.379 (4)
C2—H2B	0.9900	Cl4—O43	1.381 (5)
C15—C14	1.377 (4)	O1—H102	0.76 (4)
C15—H15	0.9500	O1—H101	0.77 (5)
C4—N1—C10	109.9 (2)	C11—C12—H12	120.2
C4—N1—C1	112.7 (2)	C13—C12—H12	120.2
C10—N1—C1	113.11 (19)	N2—C16—C17	110.9 (2)
C16—N2—C22	114.3 (2)	N2—C16—H16A	109.5
C16—N2—C3	111.0 (2)	C17—C16—H16A	109.5
C22—N2—C3	115.6 (2)	N2—C16—H16B	109.5
C15—N4—C11	123.3 (3)	C17—C16—H16B	109.5
C15—N4—H4N	118 (3)	H16A—C16—H16B	108.0
C11—N4—H4N	119 (3)	N6—C27—C26	120.1 (3)
N1—C1—C2	115.6 (2)	N6—C27—H27	119.9
N1—C1—H1A	108.4	C26—C27—H27	119.9
C2—C1—H1A	108.4	C27—C26—C25	118.7 (3)
N1—C1—H1B	108.4	C27—C26—H26	120.7
C2—C1—H1B	108.4	C25—C26—H26	120.7
H1A—C1—H1B	107.4	N3—C9—C8	119.4 (3)
N2—C3—C2	111.8 (2)	N3—C9—H9	120.3
N2—C3—H3A	109.3	C8—C9—H9	120.3
C2—C3—H3A	109.3	C15—C14—C13	118.7 (3)
N2—C3—H3B	109.3	C15—C14—H14	120.6
C2—C3—H3B	109.3	C13—C14—H14	120.6
H3A—C3—H3B	107.9	C17—C18—C19	118.9 (3)
C27—N6—C23	123.5 (2)	C17—C18—H18	120.5
C27—N6—H6N	122 (2)	C19—C18—H18	120.5
C23—N6—H6N	114 (2)	C12—C13—C14	120.1 (3)
C17—N5—C21	124.0 (3)	C12—C13—H13	119.9
C17—N5—H5N	114 (3)	C14—C13—H13	119.9
C21—N5—H5N	122 (3)	C18—C19—C20	120.3 (3)
C5—N3—C9	123.7 (3)	C18—C19—H19	119.9
C5—N3—H3N	120 (3)	C20—C19—H19	119.9
C9—N3—H3N	116 (3)	C9—C8—C7	118.9 (3)
N1—C4—C5	112.4 (2)	C9—C8—H8	120.6
N1—C4—H4A	109.1	C7—C8—H8	120.6
C5—C4—H4A	109.1	N5—C21—C20	119.0 (3)
N1—C4—H4B	109.1	N5—C21—H21	120.5
C5—C4—H4B	109.1	C20—C21—H21	120.5
H4A—C4—H4B	107.9	C7—C6—C5	119.7 (3)
N2—C22—C23	114.4 (2)	C7—C6—H6	120.1
N2—C22—H22A	108.7	C5—C6—H6	120.1
C23—C22—H22A	108.7	C26—C25—C24	119.6 (3)
N2—C22—H22B	108.7	C26—C25—H25	120.2
C23—C22—H22B	108.7	C24—C25—H25	120.2
H22A—C22—H22B	107.6	C21—C20—C19	119.1 (3)
N1—C10—C11	112.7 (2)	C21—C20—H20	120.4
N1—C10—H10A	109.0	C19—C20—H20	120.4
C11—C10—H10A	109.0	C6—C7—C8	120.2 (3)
N1—C10—H10B	109.0	C6—C7—H7	119.9
C11—C10—H10B	109.0	C8—C7—H7	119.9
H10A—C10—H10B	107.8	O12—Cl1—O14	110.69 (14)
N3—C5—C6	118.0 (3)	O12—Cl1—O13	109.99 (14)
N3—C5—C4	118.7 (2)	O14—Cl1—O13	110.62 (15)
C6—C5—C4	123.1 (3)	O12—Cl1—O11	108.75 (12)
N5—C17—C18	118.7 (3)	O14—Cl1—O11	108.48 (14)
N5—C17—C16	117.1 (2)	O13—Cl1—O11	108.25 (14)
C18—C17—C16	124.1 (3)	O22—Cl2—O24	112.0 (2)
C23—C24—C25	120.7 (3)	O22—Cl2—O23	108.57 (17)
C23—C24—H24	119.6	O24—Cl2—O23	107.53 (18)
C25—C24—H24	119.6	O22—Cl2—O21	109.80 (16)
N4—C11—C12	118.5 (3)	O24—Cl2—O21	110.36 (17)
N4—C11—C10	117.8 (2)	O23—Cl2—O21	108.43 (14)
C12—C11—C10	123.6 (2)	O33—Cl3—O34	106.1 (5)
N6—C23—C24	117.3 (3)	O33—Cl3—O32	108.8 (4)
N6—C23—C22	119.1 (2)	O34—Cl3—O32	108.9 (4)
C24—C23—C22	123.5 (2)	O33—Cl3—O31	108.5 (3)
C3—C2—C1	110.8 (2)	O34—Cl3—O31	109.9 (3)
C3—C2—H2A	109.5	O32—Cl3—O31	114.3 (2)
C1—C2—H2A	109.5	O44—Cl4—O41	114.0 (5)
C3—C2—H2B	109.5	O44—Cl4—O42	107.1 (4)
C1—C2—H2B	109.5	O41—Cl4—O42	117.2 (5)
H2A—C2—H2B	108.1	O44—Cl4—O43	113.3 (6)
N4—C15—C14	119.7 (3)	O41—Cl4—O43	102.4 (3)
N4—C15—H15	120.2	O42—Cl4—O43	102.3 (5)
C14—C15—H15	120.2	H102—O1—H101	111 (5)
C11—C12—C13	119.7 (3)
C4—N1—C1—C2	68.0 (3)	N1—C1—C2—C3	−178.8 (2)
C10—N1—C1—C2	−57.5 (3)	C11—N4—C15—C14	0.1 (4)
C16—N2—C3—C2	−161.5 (2)	N4—C11—C12—C13	0.0 (4)
C22—N2—C3—C2	66.1 (3)	C10—C11—C12—C13	177.1 (3)
C10—N1—C4—C5	−157.3 (2)	C22—N2—C16—C17	−138.2 (2)
C1—N1—C4—C5	75.5 (3)	C3—N2—C16—C17	88.8 (3)
C16—N2—C22—C23	−72.1 (3)	N5—C17—C16—N2	13.3 (3)
C3—N2—C22—C23	58.7 (3)	C18—C17—C16—N2	−170.2 (3)
C4—N1—C10—C11	166.5 (2)	C23—N6—C27—C26	1.0 (4)
C1—N1—C10—C11	−66.5 (3)	N6—C27—C26—C25	−1.3 (5)
C9—N3—C5—C6	−0.8 (4)	C5—N3—C9—C8	−1.1 (4)
C9—N3—C5—C4	174.4 (3)	N4—C15—C14—C13	−0.8 (4)
N1—C4—C5—N3	20.6 (3)	N5—C17—C18—C19	1.0 (4)
N1—C4—C5—C6	−164.4 (3)	C16—C17—C18—C19	−175.4 (3)
C21—N5—C17—C18	0.9 (4)	C11—C12—C13—C14	−0.7 (4)
C21—N5—C17—C16	177.5 (3)	C15—C14—C13—C12	1.1 (5)
C15—N4—C11—C12	0.3 (4)	C17—C18—C19—C20	−1.6 (5)
C15—N4—C11—C10	−177.0 (2)	N3—C9—C8—C7	1.8 (5)
N1—C10—C11—N4	−42.1 (3)	C17—N5—C21—C20	−2.1 (5)
N1—C10—C11—C12	140.8 (2)	N3—C5—C6—C7	1.9 (5)
C27—N6—C23—C24	0.5 (4)	C4—C5—C6—C7	−173.1 (3)
C27—N6—C23—C22	−177.9 (3)	C27—C26—C25—C24	0.1 (5)
C25—C24—C23—N6	−1.6 (4)	C23—C24—C25—C26	1.3 (4)
C25—C24—C23—C22	176.7 (3)	N5—C21—C20—C19	1.4 (5)
N2—C22—C23—N6	85.1 (3)	C18—C19—C20—C21	0.4 (5)
N2—C22—C23—C24	−93.2 (3)	C5—C6—C7—C8	−1.2 (6)
N2—C3—C2—C1	175.3 (2)	C9—C8—C7—C6	−0.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O11^i	0.88 (4)	2.00 (4)	2.845 (3)	160 (4)
N3—H3N···N1	0.88 (4)	2.38 (4)	2.737 (3)	105 (3)
N4—H4N···O1^i	0.87 (4)	2.57 (4)	3.137 (3)	124 (3)
N5—H5N···N2	0.78 (4)	2.23 (4)	2.659 (3)	115 (4)
N6—H6N···O1	0.90 (4)	1.93 (4)	2.810 (3)	165 (3)
O1—H102···O21	0.76 (4)	2.14 (4)	2.876 (3)	163 (4)
O1—H101···O33^ii	0.77 (5)	2.41 (5)	3.088 (7)	147 (5)

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