Bis(cucurbit[6]uril) bis­(hexane-1,6-diyldipyridinium) tetra­bromide trideca­hydrate

In the crystal structure of the title compound, 2C₃₆H₃₆N₂₄O₁₂·2C₁₆H₂₂N₂²⁺·4Br^-·13H₂O, the host cucurbituril is threaded by the guest hexane-1,6-diyldipyridinium cation to form a pseudorotaxane. Two Br^- anions form hydrogen bonds with two solvent water mol­ecules, while the other solvent water mol­ecules inter­act with the carbonyl O atoms at the rims of the cucurbituril.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.033
• wR factor = 0.085
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact  H5B    ..  H5B     ..       2.09 Ang.
PLAT415_ALERT_2_B Short Inter D-H..H-X       H24A   ..  H4WD    ..       2.01 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C13    ..  O4W     ..       2.90 Ang.
PLAT432_ALERT_2_B Short Inter X...Y Contact  C14    ..  O4W     ..       2.80 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................       5.00 Perc.
PLAT411_ALERT_2_C Short Inter H...H Contact  H6B    ..  H9      ..       2.13 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C23     ..       2.93 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          6
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          7
              Br

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   8 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
   6 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: WinGX (Farrugia, 1999).

bis(cucurbit[6]uril) bis(hexane-1,6-diyldipyridinium) tetrabromide tridecahydrate

Crystal data

2C36H36N24O12·2C16H22N2^2+·4Br^−·13H2O	F(000) = 1566
Mr = 3032.34	Dx = 1.667 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7483 reflections
a = 12.7444 (6) Å	θ = 1.7–28.3°
b = 20.2909 (8) Å	µ = 1.44 mm^−1
c = 12.1950 (5) Å	T = 123 K
β = 106.732 (2)°	Prism, colourless
V = 3020.1 (2) Å^3	0.20 × 0.18 × 0.15 mm
Z = 1

Data collection

Bruker SMART CCD area-detector diffractometer	7483 independent reflections
Radiation source: fine-focus sealed tube	6334 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −16→16
Tmin = 0.762, Tmax = 0.813	k = −26→26
32085 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0394P)^2 + 1.9327P] where P = (Fo^2 + 2Fc^2)/3
7483 reflections	(Δ/σ)max < 0.001
457 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.58 e Å^−3

Special details

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	Occ. (<1)
C1	0.14840 (12)	−0.04328 (9)	0.33582 (14)	0.0160 (3)
C2	0.15931 (13)	0.00307 (8)	0.16349 (14)	0.0161 (3)
H2	0.1009	−0.0031	0.0894	0.019*
C3	0.12766 (13)	0.05742 (8)	0.23790 (13)	0.0150 (3)
H3	0.0522	0.0748	0.2015	0.018*
C4	0.28350 (13)	0.09086 (9)	0.18680 (13)	0.0161 (3)
C5	0.09178 (13)	0.05003 (9)	0.43321 (14)	0.0171 (3)
H5A	0.0263	0.0770	0.3967	0.021*
H5B	0.0681	0.0131	0.4736	0.021*
C6	0.21022 (14)	0.17066 (8)	0.29802 (14)	0.0174 (3)
H6A	0.1339	0.1870	0.2795	0.021*
H6B	0.2523	0.2019	0.2648	0.021*
C7	0.21391 (13)	0.07058 (9)	0.62706 (14)	0.0167 (3)
C8	0.19151 (13)	0.15857 (8)	0.49871 (14)	0.0152 (3)
H8	0.1228	0.1854	0.4774	0.018*
C9	0.26937 (13)	0.17967 (8)	0.61633 (14)	0.0162 (3)
H9	0.2380	0.2171	0.6500	0.019*
C10	0.35506 (14)	0.19890 (8)	0.47369 (14)	0.0161 (3)
C11	0.33900 (13)	0.11691 (9)	0.80461 (14)	0.0192 (3)
H11A	0.3291	0.1585	0.8428	0.023*
H11B	0.3088	0.0807	0.8408	0.023*
C12	0.45850 (14)	0.23381 (9)	0.66867 (15)	0.0189 (3)
H12A	0.4924	0.2639	0.6247	0.023*
H12B	0.4289	0.2612	0.7201	0.023*
C13	0.50178 (14)	0.04571 (9)	0.85730 (14)	0.0188 (3)
C14	0.53503 (14)	0.15819 (9)	0.84063 (15)	0.0195 (3)
H14	0.5260	0.1906	0.8991	0.023*
C15	0.64605 (14)	0.12107 (9)	0.88207 (15)	0.0190 (3)
H15	0.6906	0.1371	0.9589	0.023*
C16	0.63863 (14)	0.17880 (9)	0.71314 (15)	0.0194 (3)
C17	0.81223 (14)	0.12052 (9)	0.80413 (16)	0.0205 (4)
H17A	0.8402	0.1530	0.7588	0.025*
H17B	0.8560	0.1252	0.8852	0.025*
C18	0.31148 (14)	−0.00046 (9)	0.06526 (14)	0.0190 (3)
H18A	0.2539	−0.0175	−0.0018	0.023*
H18B	0.3517	0.0346	0.0378	0.023*
N1	0.17164 (11)	−0.05497 (7)	0.23459 (12)	0.0172 (3)
N2	0.13481 (11)	0.02341 (7)	0.34494 (11)	0.0158 (3)
N3	0.25961 (11)	0.02805 (7)	0.14531 (11)	0.0161 (3)
N4	0.20997 (11)	0.10719 (7)	0.24525 (12)	0.0171 (3)
N5	0.16943 (12)	0.08996 (7)	0.51586 (12)	0.0169 (3)
N6	0.27762 (12)	0.12078 (7)	0.68459 (12)	0.0178 (3)
N7	0.25670 (11)	0.16990 (7)	0.42099 (12)	0.0163 (3)
N8	0.36864 (11)	0.19910 (7)	0.58939 (11)	0.0167 (3)
N9	0.45495 (12)	0.10566 (8)	0.82314 (15)	0.0256 (3)
N10	0.61323 (11)	0.05338 (7)	0.88684 (12)	0.0181 (3)
N11	0.54204 (12)	0.19088 (8)	0.73743 (12)	0.0206 (3)
N12	0.69864 (12)	0.13587 (7)	0.79441 (13)	0.0203 (3)
O1	0.14108 (10)	−0.08456 (6)	0.40598 (10)	0.0203 (3)
O2	0.19797 (10)	0.01750 (6)	0.66703 (10)	0.0212 (3)
O3	0.45272 (10)	−0.00520 (6)	0.86171 (10)	0.0219 (3)
O4	0.35603 (10)	0.12597 (6)	0.17393 (10)	0.0201 (3)
O5	0.41948 (10)	0.22075 (6)	0.42568 (10)	0.0208 (3)
O6	0.66775 (10)	0.20317 (7)	0.63558 (11)	0.0249 (3)
Br1	−0.120949 (16)	−0.171673 (10)	0.080682 (16)	0.02693 (6)
C19	0.72785 (17)	0.18768 (9)	0.41029 (15)	0.0252 (4)
H19	0.6980	0.2024	0.4689	0.030*
C20	0.82068 (17)	0.21729 (10)	0.39629 (17)	0.0306 (5)
H20	0.8549	0.2525	0.4449	0.037*
C21	0.86316 (15)	0.19523 (10)	0.31093 (18)	0.0293 (4)
H21	0.9261	0.2158	0.2993	0.035*
C22	0.81433 (15)	0.14342 (10)	0.24271 (17)	0.0272 (4)
H22	0.8439	0.1273	0.1847	0.033*
C23	0.72197 (15)	0.11513 (9)	0.25948 (16)	0.0226 (4)
H23	0.6878	0.0791	0.2130	0.027*
C24	0.57753 (14)	0.10860 (10)	0.35465 (16)	0.0229 (4)
H24A	0.5359	0.0884	0.2811	0.027*
H24B	0.5316	0.1439	0.3729	0.027*
C25	0.59907 (14)	0.05691 (9)	0.44750 (16)	0.0211 (4)
H25A	0.6369	0.0773	0.5222	0.025*
H25B	0.6475	0.0223	0.4316	0.025*
C26	0.49180 (14)	0.02584 (10)	0.45349 (16)	0.0234 (4)
H26A	0.4432	0.0609	0.4676	0.028*
H26B	0.4548	0.0053	0.3787	0.028*
N13	0.67983 (11)	0.13817 (7)	0.34123 (12)	0.0178 (3)
O1W	0.96939 (11)	0.18048 (7)	0.09445 (12)	0.0284 (3)
H1WA	1.0127	0.1725	0.0578	0.036 (7)*
H1WB	0.9792	0.2223	0.1085	0.047 (8)*
O2W	0.09247 (11)	0.01303 (7)	0.84361 (11)	0.0265 (3)
H2WA	0.1180	0.0123	0.7874	0.047 (8)*
H2WB	0.0981	0.0561	0.8612	0.051 (8)*
O3W	−0.01630 (12)	−0.18612 (7)	0.35809 (12)	0.0313 (3)
H3WA	0.0351	−0.1563	0.3744	0.066 (10)*
H3WB	−0.0435	−0.1797	0.2868	0.061 (9)*
O4W	0.4886 (4)	−0.1272 (2)	0.9443 (4)	0.0157 (9)	0.25
H4WC	0.4809	−0.0869	0.9591	0.019*	0.25
H4WD	0.4823	−0.1299	0.8731	0.019*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0092 (7)	0.0156 (8)	0.0217 (7)	−0.0005 (6)	0.0024 (6)	−0.0009 (7)
C2	0.0129 (7)	0.0172 (8)	0.0173 (7)	0.0011 (6)	0.0030 (6)	−0.0023 (6)
C3	0.0132 (7)	0.0141 (8)	0.0178 (7)	0.0002 (6)	0.0046 (6)	0.0003 (6)
C4	0.0133 (7)	0.0180 (8)	0.0157 (7)	0.0032 (7)	0.0018 (6)	0.0028 (6)
C5	0.0155 (7)	0.0160 (8)	0.0214 (8)	−0.0021 (7)	0.0077 (6)	−0.0012 (7)
C6	0.0199 (8)	0.0133 (8)	0.0192 (7)	0.0004 (7)	0.0058 (6)	0.0024 (7)
C7	0.0149 (7)	0.0169 (8)	0.0217 (7)	0.0022 (7)	0.0106 (6)	−0.0012 (7)
C8	0.0153 (7)	0.0123 (8)	0.0196 (7)	0.0010 (6)	0.0075 (6)	−0.0004 (6)
C9	0.0150 (7)	0.0151 (8)	0.0204 (7)	0.0014 (6)	0.0080 (6)	−0.0011 (6)
C10	0.0187 (8)	0.0089 (8)	0.0215 (7)	0.0023 (6)	0.0071 (6)	0.0007 (6)
C11	0.0142 (7)	0.0249 (10)	0.0197 (8)	0.0015 (7)	0.0066 (6)	−0.0007 (7)
C12	0.0170 (8)	0.0140 (8)	0.0256 (8)	−0.0014 (7)	0.0060 (6)	−0.0029 (7)
C13	0.0171 (8)	0.0220 (9)	0.0175 (7)	0.0015 (7)	0.0055 (6)	−0.0046 (7)
C14	0.0166 (8)	0.0195 (9)	0.0232 (8)	0.0011 (7)	0.0072 (6)	−0.0046 (7)
C15	0.0150 (7)	0.0207 (9)	0.0209 (8)	0.0003 (7)	0.0047 (6)	−0.0058 (7)
C16	0.0158 (8)	0.0174 (9)	0.0248 (8)	−0.0025 (7)	0.0057 (6)	−0.0087 (7)
C17	0.0139 (8)	0.0154 (9)	0.0326 (9)	−0.0023 (7)	0.0075 (7)	−0.0065 (7)
C18	0.0175 (8)	0.0250 (9)	0.0149 (7)	0.0043 (7)	0.0055 (6)	0.0006 (7)
N1	0.0175 (7)	0.0117 (7)	0.0235 (7)	0.0005 (6)	0.0075 (5)	−0.0006 (6)
N2	0.0170 (6)	0.0132 (7)	0.0177 (6)	0.0001 (6)	0.0058 (5)	0.0005 (5)
N3	0.0147 (6)	0.0165 (7)	0.0185 (6)	0.0002 (6)	0.0069 (5)	−0.0008 (6)
N4	0.0170 (7)	0.0142 (7)	0.0215 (7)	−0.0023 (6)	0.0081 (5)	−0.0011 (6)
N5	0.0208 (7)	0.0125 (7)	0.0182 (6)	−0.0023 (6)	0.0068 (5)	−0.0007 (5)
N6	0.0181 (7)	0.0189 (7)	0.0179 (6)	−0.0024 (6)	0.0076 (5)	0.0005 (6)
N7	0.0164 (6)	0.0158 (7)	0.0181 (6)	−0.0019 (6)	0.0073 (5)	0.0001 (6)
N8	0.0154 (6)	0.0163 (7)	0.0189 (6)	−0.0017 (6)	0.0059 (5)	−0.0001 (6)
N9	0.0134 (7)	0.0179 (8)	0.0443 (9)	0.0009 (6)	0.0062 (6)	−0.0027 (7)
N10	0.0146 (6)	0.0181 (8)	0.0221 (7)	0.0016 (6)	0.0060 (5)	−0.0003 (6)
N11	0.0157 (7)	0.0254 (8)	0.0217 (7)	0.0041 (6)	0.0069 (5)	−0.0020 (6)
N12	0.0146 (7)	0.0170 (8)	0.0314 (8)	−0.0001 (6)	0.0101 (6)	−0.0013 (6)
O1	0.0202 (6)	0.0147 (6)	0.0257 (6)	−0.0021 (5)	0.0062 (5)	0.0032 (5)
O2	0.0240 (6)	0.0175 (6)	0.0242 (6)	−0.0010 (5)	0.0103 (5)	0.0030 (5)
O3	0.0202 (6)	0.0219 (7)	0.0237 (6)	−0.0019 (5)	0.0064 (5)	−0.0019 (5)
O4	0.0162 (6)	0.0212 (7)	0.0233 (6)	−0.0033 (5)	0.0063 (5)	0.0013 (5)
O5	0.0221 (6)	0.0189 (6)	0.0241 (6)	−0.0045 (5)	0.0107 (5)	0.0021 (5)
O6	0.0223 (6)	0.0267 (7)	0.0289 (6)	−0.0004 (6)	0.0125 (5)	−0.0020 (6)
Br1	0.02773 (10)	0.02703 (11)	0.02898 (10)	−0.00031 (8)	0.01285 (7)	−0.00436 (8)
C19	0.0345 (10)	0.0182 (9)	0.0205 (8)	0.0015 (8)	0.0044 (7)	0.0014 (7)
C20	0.0353 (11)	0.0179 (10)	0.0279 (9)	−0.0088 (8)	−0.0077 (8)	0.0069 (8)
C21	0.0188 (9)	0.0266 (10)	0.0389 (11)	−0.0032 (8)	0.0025 (8)	0.0158 (9)
C22	0.0223 (9)	0.0274 (10)	0.0350 (10)	0.0008 (8)	0.0130 (8)	0.0066 (9)
C23	0.0231 (9)	0.0188 (9)	0.0272 (9)	−0.0008 (7)	0.0092 (7)	−0.0007 (7)
C24	0.0151 (8)	0.0262 (10)	0.0297 (9)	0.0005 (7)	0.0101 (7)	0.0043 (8)
C25	0.0153 (8)	0.0197 (9)	0.0294 (9)	0.0000 (7)	0.0079 (7)	0.0016 (7)
C26	0.0155 (8)	0.0252 (10)	0.0307 (9)	−0.0017 (7)	0.0087 (7)	0.0037 (8)
N13	0.0163 (7)	0.0155 (7)	0.0219 (7)	0.0004 (6)	0.0059 (5)	0.0033 (6)
O1W	0.0280 (7)	0.0294 (8)	0.0310 (7)	0.0053 (6)	0.0138 (6)	0.0081 (6)
O2W	0.0258 (7)	0.0275 (8)	0.0266 (6)	−0.0062 (6)	0.0083 (5)	0.0013 (6)
O3W	0.0303 (7)	0.0324 (8)	0.0304 (7)	−0.0119 (7)	0.0075 (6)	0.0044 (6)
O4W	0.032 (3)	0.006 (2)	0.016 (2)	0.0002 (19)	0.0183 (19)	0.0016 (17)

Geometric parameters (Å, º)

C1—O1	1.220 (2)	C14—C15	1.553 (2)
C1—N1	1.371 (2)	C14—H14	1.0000
C1—N2	1.373 (2)	C15—N10	1.442 (2)
C2—N1	1.444 (2)	C15—N12	1.447 (2)
C2—N3	1.450 (2)	C15—H15	1.0000
C2—C3	1.554 (2)	C16—O6	1.216 (2)
C2—H2	1.0000	C16—N11	1.369 (2)
C3—N4	1.440 (2)	C16—N12	1.375 (2)
C3—N2	1.456 (2)	C17—N1^i	1.446 (2)
C3—H3	1.0000	C17—N12	1.452 (2)
C4—O4	1.213 (2)	C17—H17A	0.9900
C4—N4	1.371 (2)	C17—H17B	0.9900
C4—N3	1.373 (2)	C18—N10^i	1.446 (2)
C5—N5	1.441 (2)	C18—N3	1.448 (2)
C5—N2	1.446 (2)	C18—H18A	0.9900
C5—H5A	0.9900	C18—H18B	0.9900
C5—H5B	0.9900	N1—C17^i	1.446 (2)
C6—N4	1.439 (2)	N10—C18^i	1.446 (2)
C6—N7	1.445 (2)	C19—N13	1.340 (2)
C6—H6A	0.9900	C19—C20	1.381 (3)
C6—H6B	0.9900	C19—H19	0.9500
C7—O2	1.223 (2)	C20—C21	1.379 (3)
C7—N6	1.364 (2)	C20—H20	0.9500
C7—N5	1.368 (2)	C21—C22	1.373 (3)
C8—N7	1.447 (2)	C21—H21	0.9500
C8—N5	1.447 (2)	C22—C23	1.377 (3)
C8—C9	1.551 (2)	C22—H22	0.9500
C8—H8	1.0000	C23—N13	1.345 (2)
C9—N6	1.443 (2)	C23—H23	0.9500
C9—N8	1.450 (2)	C24—N13	1.486 (2)
C9—H9	1.0000	C24—C25	1.510 (3)
C10—O5	1.221 (2)	C24—H24A	0.9900
C10—N7	1.366 (2)	C24—H24B	0.9900
C10—N8	1.371 (2)	C25—C26	1.526 (2)
C11—N9	1.447 (2)	C25—H25A	0.9900
C11—N6	1.450 (2)	C25—H25B	0.9900
C11—H11A	0.9900	C26—C26^i	1.514 (4)
C11—H11B	0.9900	C26—H26A	0.9900
C12—N11	1.443 (2)	C26—H26B	0.9900
C12—N8	1.451 (2)	O1W—H1WA	0.8206
C12—H12A	0.9900	O1W—H1WB	0.8669
C12—H12B	0.9900	O2W—H2WA	0.8387
C13—O3	1.217 (2)	O2W—H2WB	0.8971
C13—N9	1.366 (2)	O3W—H3WA	0.8714
C13—N10	1.370 (2)	O3W—H3WB	0.8486
C14—N11	1.448 (2)	O4W—H4WC	0.8499
C14—N9	1.448 (2)	O4W—H4WD	0.8501
O1—C1—N1	126.36 (16)	H17A—C17—H17B	107.7
O1—C1—N2	125.66 (15)	N10^i—C18—N3	113.76 (13)
N1—C1—N2	107.97 (14)	N10^i—C18—H18A	108.8
N1—C2—N3	115.38 (13)	N3—C18—H18A	108.8
N1—C2—C3	103.30 (12)	N10^i—C18—H18B	108.8
N3—C2—C3	103.27 (13)	N3—C18—H18B	108.8
N1—C2—H2	111.4	H18A—C18—H18B	107.7
N3—C2—H2	111.4	C1—N1—C2	112.67 (14)
C3—C2—H2	111.4	C1—N1—C17^i	122.77 (15)
N4—C3—N2	114.84 (13)	C2—N1—C17^i	123.73 (14)
N4—C3—C2	103.13 (13)	C1—N2—C5	120.81 (14)
N2—C3—C2	103.14 (13)	C1—N2—C3	111.80 (13)
N4—C3—H3	111.7	C5—N2—C3	123.43 (14)
N2—C3—H3	111.7	C4—N3—C18	121.58 (14)
C2—C3—H3	111.7	C4—N3—C2	112.33 (13)
O4—C4—N4	125.87 (16)	C18—N3—C2	123.84 (14)
O4—C4—N3	126.45 (15)	C4—N4—C6	122.32 (14)
N4—C4—N3	107.68 (14)	C4—N4—C3	113.13 (14)
N5—C5—N2	113.54 (13)	C6—N4—C3	124.27 (13)
N5—C5—H5A	108.9	C7—N5—C5	122.45 (14)
N2—C5—H5A	108.9	C7—N5—C8	112.17 (14)
N5—C5—H5B	108.9	C5—N5—C8	124.23 (14)
N2—C5—H5B	108.9	C7—N6—C9	112.83 (14)
H5A—C5—H5B	107.7	C7—N6—C11	123.17 (15)
N4—C6—N7	113.69 (14)	C9—N6—C11	123.77 (14)
N4—C6—H6A	108.8	C10—N7—C6	122.00 (14)
N7—C6—H6A	108.8	C10—N7—C8	112.47 (13)
N4—C6—H6B	108.8	C6—N7—C8	122.70 (14)
N7—C6—H6B	108.8	C10—N8—C9	111.86 (13)
H6A—C6—H6B	107.7	C10—N8—C12	121.92 (14)
O2—C7—N6	126.52 (16)	C9—N8—C12	123.63 (13)
O2—C7—N5	125.39 (16)	C13—N9—C11	121.65 (15)
N6—C7—N5	108.09 (14)	C13—N9—C14	112.51 (14)
N7—C8—N5	114.81 (13)	C11—N9—C14	123.47 (15)
N7—C8—C9	103.11 (13)	C13—N10—C15	112.86 (14)
N5—C8—C9	103.36 (13)	C13—N10—C18^i	122.61 (15)
N7—C8—H8	111.6	C15—N10—C18^i	123.85 (14)
N5—C8—H8	111.6	C16—N11—C12	122.79 (15)
C9—C8—H8	111.6	C16—N11—C14	112.99 (15)
N6—C9—N8	115.63 (14)	C12—N11—C14	124.19 (14)
N6—C9—C8	103.06 (13)	C16—N12—C15	112.60 (14)
N8—C9—C8	103.48 (12)	C16—N12—C17	121.98 (15)
N6—C9—H9	111.4	C15—N12—C17	123.91 (15)
N8—C9—H9	111.4	N13—C19—C20	120.08 (18)
C8—C9—H9	111.4	N13—C19—H19	120.0
O5—C10—N7	125.69 (15)	C20—C19—H19	120.0
O5—C10—N8	126.12 (16)	C21—C20—C19	119.25 (18)
N7—C10—N8	108.19 (14)	C21—C20—H20	120.4
N9—C11—N6	113.34 (14)	C19—C20—H20	120.4
N9—C11—H11A	108.9	C22—C21—C20	119.86 (18)
N6—C11—H11A	108.9	C22—C21—H21	120.1
N9—C11—H11B	108.9	C20—C21—H21	120.1
N6—C11—H11B	108.9	C21—C22—C23	119.13 (19)
H11A—C11—H11B	107.7	C21—C22—H22	120.4
N11—C12—N8	113.77 (15)	C23—C22—H22	120.4
N11—C12—H12A	108.8	N13—C23—C22	120.40 (18)
N8—C12—H12A	108.8	N13—C23—H23	119.8
N11—C12—H12B	108.8	C22—C23—H23	119.8
N8—C12—H12B	108.8	N13—C24—C25	112.78 (14)
H12A—C12—H12B	107.7	N13—C24—H24A	109.0
O3—C13—N9	125.77 (16)	C25—C24—H24A	109.0
O3—C13—N10	126.29 (17)	N13—C24—H24B	109.0
N9—C13—N10	107.93 (15)	C25—C24—H24B	109.0
N11—C14—N9	115.23 (15)	H24A—C24—H24B	107.8
N11—C14—C15	103.10 (13)	C24—C25—C26	110.55 (14)
N9—C14—C15	103.20 (14)	C24—C25—H25A	109.5
N11—C14—H14	111.6	C26—C25—H25A	109.5
N9—C14—H14	111.6	C24—C25—H25B	109.5
C15—C14—H14	111.6	C26—C25—H25B	109.5
N10—C15—N12	115.40 (14)	H25A—C25—H25B	108.1
N10—C15—C14	103.14 (13)	C26^i—C26—C25	112.92 (18)
N12—C15—C14	103.36 (14)	C26^i—C26—H26A	109.0
N10—C15—H15	111.4	C25—C26—H26A	109.0
N12—C15—H15	111.4	C26^i—C26—H26B	109.0
C14—C15—H15	111.4	C25—C26—H26B	109.0
O6—C16—N11	126.19 (17)	H26A—C26—H26B	107.8
O6—C16—N12	125.97 (16)	C19—N13—C23	121.24 (16)
N11—C16—N12	107.81 (15)	C19—N13—C24	119.32 (15)
N1^i—C17—N12	113.76 (14)	C23—N13—C24	119.43 (15)
N1^i—C17—H17A	108.8	H1WA—O1W—H1WB	102.7
N12—C17—H17A	108.8	H2WA—O2W—H2WB	101.0
N1^i—C17—H17B	108.8	H3WA—O3W—H3WB	100.7
N12—C17—H17B	108.8	H4WC—O4W—H4WD	107.3
N1—C2—C3—N4	124.07 (13)	O5—C10—N7—C6	−9.4 (3)
N3—C2—C3—N4	3.52 (15)	N8—C10—N7—C6	170.63 (15)
N1—C2—C3—N2	4.24 (15)	O5—C10—N7—C8	−170.82 (16)
N3—C2—C3—N2	−116.31 (13)	N8—C10—N7—C8	9.22 (19)
N7—C8—C9—N6	−121.66 (13)	N4—C6—N7—C10	110.06 (17)
N5—C8—C9—N6	−1.78 (15)	N4—C6—N7—C8	−90.43 (18)
N7—C8—C9—N8	−0.85 (16)	N5—C8—N7—C10	−116.64 (16)
N5—C8—C9—N8	119.02 (13)	C9—C8—N7—C10	−4.99 (18)
N11—C14—C15—N10	−122.61 (14)	N5—C8—N7—C6	82.10 (19)
N9—C14—C15—N10	−2.34 (17)	C9—C8—N7—C6	−166.25 (14)
N11—C14—C15—N12	−2.06 (17)	O5—C10—N8—C9	170.25 (16)
N9—C14—C15—N12	118.21 (15)	N7—C10—N8—C9	−9.79 (19)
O1—C1—N1—C2	171.84 (15)	O5—C10—N8—C12	7.9 (3)
N2—C1—N1—C2	−8.25 (18)	N7—C10—N8—C12	−172.15 (15)
O1—C1—N1—C17^i	1.9 (3)	N6—C9—N8—C10	118.31 (16)
N2—C1—N1—C17^i	−178.18 (14)	C8—C9—N8—C10	6.43 (18)
N3—C2—N1—C1	114.11 (15)	N6—C9—N8—C12	−79.7 (2)
C3—C2—N1—C1	2.19 (17)	C8—C9—N8—C12	168.44 (15)
N3—C2—N1—C17^i	−76.08 (19)	N11—C12—N8—C10	−107.73 (18)
C3—C2—N1—C17^i	172.01 (14)	N11—C12—N8—C9	92.02 (19)
O1—C1—N2—C5	−10.4 (2)	O3—C13—N9—C11	9.8 (3)
N1—C1—N2—C5	169.66 (14)	N10—C13—N9—C11	−169.49 (15)
O1—C1—N2—C3	−168.80 (15)	O3—C13—N9—C14	172.90 (16)
N1—C1—N2—C3	11.29 (18)	N10—C13—N9—C14	−6.4 (2)
N5—C5—N2—C1	114.70 (16)	N6—C11—N9—C13	−105.56 (19)
N5—C5—N2—C3	−89.52 (18)	N6—C11—N9—C14	93.2 (2)
N4—C3—N2—C1	−120.97 (15)	N11—C14—N9—C13	116.96 (17)
C2—C3—N2—C1	−9.55 (17)	C15—C14—N9—C13	5.38 (19)
N4—C3—N2—C5	81.33 (19)	N11—C14—N9—C11	−80.3 (2)
C2—C3—N2—C5	−167.26 (14)	C15—C14—N9—C11	168.14 (16)
O4—C4—N3—C18	−9.0 (2)	O3—C13—N10—C15	−174.60 (16)
N4—C4—N3—C18	170.66 (14)	N9—C13—N10—C15	4.67 (19)
O4—C4—N3—C2	−172.59 (15)	O3—C13—N10—C18^i	−3.7 (3)
N4—C4—N3—C2	7.07 (18)	N9—C13—N10—C18^i	175.54 (15)
N10^i—C18—N3—C4	110.92 (17)	N12—C15—N10—C13	−113.23 (16)
N10^i—C18—N3—C2	−87.42 (19)	C14—C15—N10—C13	−1.29 (18)
N1—C2—N3—C4	−118.50 (15)	N12—C15—N10—C18^i	76.0 (2)
C3—C2—N3—C4	−6.57 (17)	C14—C15—N10—C18^i	−172.02 (14)
N1—C2—N3—C18	78.34 (19)	O6—C16—N11—C12	2.4 (3)
C3—C2—N3—C18	−169.73 (14)	N12—C16—N11—C12	−179.61 (15)
O4—C4—N4—C6	1.0 (3)	O6—C16—N11—C14	−175.49 (17)
N3—C4—N4—C6	−178.64 (14)	N12—C16—N11—C14	2.5 (2)
O4—C4—N4—C3	175.15 (15)	N8—C12—N11—C16	100.28 (19)
N3—C4—N4—C3	−4.51 (18)	N8—C12—N11—C14	−82.1 (2)
N7—C6—N4—C4	−103.80 (17)	N9—C14—N11—C16	−111.82 (17)
N7—C6—N4—C3	82.74 (19)	C15—C14—N11—C16	−0.18 (19)
N2—C3—N4—C4	111.85 (16)	N9—C14—N11—C12	70.4 (2)
C2—C3—N4—C4	0.43 (17)	C15—C14—N11—C12	−178.01 (15)
N2—C3—N4—C6	−74.2 (2)	O6—C16—N12—C15	173.97 (17)
C2—C3—N4—C6	174.42 (14)	N11—C16—N12—C15	−4.0 (2)
O2—C7—N5—C5	3.7 (3)	O6—C16—N12—C17	7.5 (3)
N6—C7—N5—C5	−175.77 (14)	N11—C16—N12—C17	−170.52 (15)
O2—C7—N5—C8	171.98 (15)	N10—C15—N12—C16	115.60 (16)
N6—C7—N5—C8	−7.53 (18)	C14—C15—N12—C16	3.79 (18)
N2—C5—N5—C7	−111.09 (17)	N10—C15—N12—C17	−78.2 (2)
N2—C5—N5—C8	82.10 (19)	C14—C15—N12—C17	169.96 (15)
N7—C8—N5—C7	117.20 (15)	N1^i—C17—N12—C16	−107.70 (19)
C9—C8—N5—C7	5.69 (17)	N1^i—C17—N12—C15	87.4 (2)
N7—C8—N5—C5	−74.81 (19)	N13—C19—C20—C21	−0.1 (3)
C9—C8—N5—C5	173.69 (14)	C19—C20—C21—C22	−1.4 (3)
O2—C7—N6—C9	−173.24 (15)	C20—C21—C22—C23	1.3 (3)
N5—C7—N6—C9	6.25 (18)	C21—C22—C23—N13	0.3 (3)
O2—C7—N6—C11	1.5 (3)	N13—C24—C25—C26	−177.15 (15)
N5—C7—N6—C11	−179.00 (14)	C24—C25—C26—C26^i	−179.2 (2)
N8—C9—N6—C7	−114.73 (16)	C20—C19—N13—C23	1.8 (3)
C8—C9—N6—C7	−2.61 (17)	C20—C19—N13—C24	−177.65 (16)
N8—C9—N6—C11	70.6 (2)	C22—C23—N13—C19	−1.9 (3)
C8—C9—N6—C11	−177.31 (14)	C22—C23—N13—C24	177.55 (17)
N9—C11—N6—C7	103.21 (19)	C25—C24—N13—C19	−83.5 (2)
N9—C11—N6—C9	−82.6 (2)	C25—C24—N13—C23	97.09 (19)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···Br1^ii	0.82	2.47	3.2710 (13)	166
O1W—H1WB···O3W^iii	0.87	1.93	2.796 (2)	174
O2W—H2WA···O2	0.84	2.02	2.8496 (18)	172
O2W—H2WB···Br1^iv	0.90	2.44	3.3397 (15)	177
O3W—H3WA···O1	0.87	1.95	2.8170 (19)	176
O3W—H3WB···Br1	0.85	2.43	3.2728 (14)	175
O4W—H4WC···O3	0.85	2.01	2.663 (5)	133
O4W—H4WC···N10^v	0.85	2.59	3.116 (4)	121
O4W—H4WD···O4^i	0.85	2.29	2.765 (4)	115

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