1,4-Di­aza­bi­cyclo­[2.2.2]­octanium bis(3,5-di­nitro­benzoate) monohydrate

The title compound, C₆H₁₄N₂²⁺·2C₇H₃N₂O₆⁻·H₂O, is a mono­hydrate of a 1:2 hydrate adduct of 1,4-di­aza­bi­cyclo­[2.2.2]­octane (DABCO) and 3,5-di­nitro­benzoic acid. The (DABCOH₂)²⁺ cation adopts the role of a donor in intermolecular N—H...O hydrogen bonding, while both the 3,5-di­nitro­benzoate anions act as multiple acceptors of N—H...O, O—H...O and C—H...O hydrogen bonds. These hydrogen bonds result in the formation of a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.128
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT213_ALERT_2_C Atom C8      has ADP max/min Ratio .............       3.30 prolat
PLAT213_ALERT_2_C Atom O9      has ADP max/min Ratio .............       3.40 oblate
PLAT213_ALERT_2_C Atom C15     has ADP max/min Ratio .............       3.10 prolat
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.38 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O11    -   C20     ..       5.03 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.62
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.33
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.77
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C18    -   C20    ...       1.53 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1W    ..  C3      ..       2.95 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1W    ..  C4      ..       3.01 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C19     ..       2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O7     ..  C13     ..       2.96 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4
PLAT731_ALERT_1_C Bond    Calc     0.94(3), Rep   0.940(10) ......       3.00 su-Rat
              N2   -H1N2    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.90(3), Rep   0.900(10) ......       3.00 su-Rat
              O1W  -H1W1    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.91(3), Rep   0.910(10) ......       3.00 su-Rat
              O1W  -H2W1    1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      102(3), Rep   102.0(14) ......       2.14 su-Rat
              H1W1 -O1W  -H2W1    1.555   1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.94(3), Rep   0.940(10) ......       3.00 su-Rat
              N2   -H2#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.90(3), Rep   0.900(10) ......       3.00 su-Rat
              O1W  -H3#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.91(3), Rep   0.910(10) ......       3.00 su-Rat
              O1W  -H4#     1.555   1.555

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

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

1,4-Diazabicyclo[2.2.2]octanium 3,5-dinitrobenzoate hydrate (1/2/1)

Crystal data

C6H14N2^2+·2C7H3N2O6^−·H2O	F(000) = 1152
Mr = 554.44	Dx = 1.600 Mg m^−3
Monoclinic, P21/n	Melting point = 547–548 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.6505 (5) Å	Cell parameters from 10514 reflections
b = 10.4942 (5) Å	θ = 2.7–25.0°
c = 19.4752 (9) Å	µ = 0.14 mm^−1
β = 104.799 (1)°	T = 183 K
V = 2302.10 (18) Å^3	Block, colorless
Z = 4	0.44 × 0.32 × 0.16 mm

Data collection

Siemans SMART CCD area-detector diffractometer	3987 independent reflections
Radiation source: fine-focus sealed tube	2527 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 2.7°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.943, Tmax = 0.979	l = −20→23
10514 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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.128	w = 1/[σ^2(Fo^2) + (0.0309P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max < 0.001
4043 reflections	Δρmax = 0.38 e Å^−3
367 parameters	Δρmin = −0.44 e Å^−3
5 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0103 (11)

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
O1	0.41254 (18)	0.8045 (2)	−0.05850 (10)	0.0277 (5)
O2	0.22084 (18)	0.8344 (2)	−0.09265 (10)	0.0295 (6)
O3	0.01936 (17)	0.9737 (2)	0.08401 (11)	0.0318 (6)
O4	0.11981 (18)	1.0762 (2)	0.17760 (11)	0.0288 (6)
O5	0.56178 (17)	1.1103 (2)	0.22600 (11)	0.0257 (5)
O6	0.64253 (16)	0.96043 (19)	0.17053 (10)	0.0210 (5)
O7	0.0168 (2)	0.6351 (2)	−0.20386 (11)	0.0347 (6)
O8	−0.1735 (2)	0.6359 (2)	−0.21563 (12)	0.0415 (6)
O9	−0.31627 (19)	0.7500 (2)	−0.01027 (12)	0.0419 (7)
O10	−0.2002 (2)	0.7230 (3)	0.09475 (13)	0.0444 (7)
O11	0.22504 (17)	0.6257 (2)	0.12702 (11)	0.0293 (6)
O12	0.28812 (16)	0.58126 (18)	0.03045 (10)	0.0205 (5)
N1	0.01735 (19)	1.0356 (2)	0.36656 (12)	0.0137 (5)
H1N1	0.0861 (18)	1.046 (3)	0.4038 (12)	0.049 (11)*
N2	−0.16927 (19)	1.0035 (2)	0.26985 (12)	0.0135 (5)
H1N2	−0.237 (2)	0.993 (4)	0.2318 (14)	0.088 (15)*
N3	0.3183 (2)	0.8445 (2)	−0.04870 (12)	0.0199 (6)
N4	0.1130 (2)	1.0154 (2)	0.12243 (13)	0.0208 (6)
N5	−0.0705 (2)	0.6390 (2)	−0.17963 (13)	0.0237 (6)
N6	−0.2191 (2)	0.7256 (2)	0.03013 (15)	0.0270 (6)
C1	−0.0822 (2)	1.0027 (3)	0.39907 (15)	0.0236 (7)
H1A	−0.1013	1.0767	0.4257	0.028*
H1B	−0.0588	0.9306	0.4326	0.028*
C2	−0.1912 (3)	0.9658 (3)	0.33917 (15)	0.0252 (8)
H2A	−0.2048	0.8727	0.3400	0.030*
H2B	−0.2627	1.0098	0.3459	0.030*
C3	−0.0730 (2)	0.9235 (3)	0.25503 (16)	0.0224 (7)
H3A	−0.0516	0.9550	0.2120	0.027*
H3B	−0.1003	0.8342	0.2465	0.027*
C4	0.0359 (2)	0.9299 (3)	0.31932 (15)	0.0215 (7)
H4A	0.0455	0.8481	0.3455	0.026*
H4B	0.1085	0.9457	0.3031	0.026*
C5	−0.0125 (3)	1.1556 (3)	0.32427 (16)	0.0247 (7)
H5A	0.0479	1.1724	0.2977	0.030*
H5B	−0.0132	1.2285	0.3564	0.030*
C6	−0.1349 (3)	1.1403 (3)	0.27241 (16)	0.0229 (7)
H6A	−0.1941	1.1925	0.2883	0.027*
H6B	−0.1323	1.1696	0.2245	0.027*
C7	0.3222 (2)	0.9080 (3)	0.01929 (14)	0.0145 (6)
C8	0.2162 (2)	0.9343 (3)	0.03603 (14)	0.0159 (6)
H8	0.1417	0.9144	0.0044	0.019*
C9	0.2240 (2)	0.9906 (3)	0.10078 (14)	0.0152 (6)
C10	0.3310 (2)	1.0250 (3)	0.14709 (15)	0.0173 (6)
H10	0.3325	1.0672	0.1905	0.021*
C11	0.4363 (2)	0.9967 (3)	0.12876 (14)	0.0142 (6)
C12	0.4317 (2)	0.9352 (3)	0.06491 (14)	0.0147 (6)
H12	0.5028	0.9121	0.0527	0.018*
C13	0.5553 (2)	1.0275 (3)	0.17985 (14)	0.0163 (6)
C14	−0.0487 (2)	0.6517 (3)	−0.10205 (14)	0.0159 (6)
C15	−0.1440 (2)	0.6832 (3)	−0.07411 (15)	0.0181 (7)
H15	−0.2217	0.6956	−0.1038	0.022*
C16	−0.1200 (2)	0.6952 (3)	−0.00195 (15)	0.0161 (6)
C17	−0.0075 (2)	0.6755 (2)	0.04350 (15)	0.0159 (6)
H17	0.0053	0.6846	0.0934	0.019*
C18	0.0858 (2)	0.6422 (3)	0.01395 (14)	0.0139 (6)
C19	0.0645 (2)	0.6300 (3)	−0.05930 (14)	0.0149 (6)
H19	0.1271	0.6070	−0.0799	0.018*
C20	0.2091 (2)	0.6149 (3)	0.06218 (16)	0.0166 (7)
O1W	0.0962 (2)	0.7484 (2)	0.21375 (14)	0.0464 (7)
H1W1	0.052 (3)	0.686 (2)	0.226 (2)	0.070*
H2W1	0.144 (3)	0.704 (3)	0.1921 (18)	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0219 (13)	0.0330 (13)	0.0287 (13)	−0.0023 (10)	0.0074 (10)	−0.0083 (10)
O2	0.0226 (13)	0.0419 (15)	0.0191 (12)	−0.0118 (10)	−0.0037 (10)	−0.0056 (10)
O3	0.0083 (12)	0.0493 (15)	0.0341 (14)	−0.0019 (10)	−0.0016 (10)	0.0000 (11)
O4	0.0238 (13)	0.0324 (14)	0.0313 (14)	−0.0004 (10)	0.0089 (10)	−0.0075 (11)
O5	0.0153 (12)	0.0314 (13)	0.0250 (13)	−0.0013 (9)	−0.0050 (9)	−0.0116 (10)
O6	0.0093 (11)	0.0292 (12)	0.0197 (12)	0.0009 (9)	−0.0049 (8)	−0.0055 (9)
O7	0.0295 (14)	0.0500 (16)	0.0245 (13)	0.0068 (11)	0.0065 (11)	−0.0018 (11)
O8	0.0258 (15)	0.0649 (18)	0.0253 (13)	0.0002 (12)	−0.0090 (11)	−0.0027 (12)
O9	0.0117 (13)	0.0643 (18)	0.0486 (16)	0.0170 (11)	0.0057 (11)	0.0176 (13)
O10	0.0262 (14)	0.080 (2)	0.0309 (16)	0.0099 (13)	0.0135 (12)	0.0059 (13)
O11	0.0149 (12)	0.0540 (16)	0.0150 (13)	0.0100 (10)	−0.0034 (9)	−0.0027 (10)
O12	0.0072 (11)	0.0328 (13)	0.0192 (12)	0.0041 (9)	−0.0009 (8)	0.0013 (9)
N1	0.0053 (12)	0.0188 (13)	0.0139 (13)	−0.0023 (9)	−0.0033 (10)	0.0010 (10)
N2	0.0046 (12)	0.0191 (13)	0.0137 (13)	−0.0006 (10)	−0.0035 (10)	−0.0004 (10)
N3	0.0184 (15)	0.0202 (14)	0.0173 (14)	−0.0070 (11)	−0.0024 (11)	−0.0007 (11)
N4	0.0122 (14)	0.0228 (15)	0.0253 (16)	0.0015 (11)	0.0013 (12)	0.0067 (12)
N5	0.0216 (16)	0.0247 (15)	0.0202 (15)	0.0028 (11)	−0.0031 (12)	0.0008 (11)
N6	0.0115 (15)	0.0336 (17)	0.0363 (18)	0.0068 (11)	0.0068 (13)	0.0083 (13)
C1	0.0101 (16)	0.045 (2)	0.0145 (16)	−0.0050 (14)	0.0005 (12)	0.0022 (14)
C2	0.0128 (16)	0.042 (2)	0.0181 (17)	−0.0092 (14)	−0.0004 (13)	0.0029 (14)
C3	0.0092 (15)	0.0291 (18)	0.0247 (18)	0.0031 (12)	−0.0033 (13)	−0.0141 (14)
C4	0.0098 (15)	0.0269 (18)	0.0245 (18)	0.0023 (12)	−0.0018 (13)	−0.0077 (14)
C5	0.0201 (18)	0.0200 (17)	0.0247 (18)	−0.0042 (13)	−0.0117 (14)	0.0034 (14)
C6	0.0181 (17)	0.0171 (17)	0.0248 (18)	−0.0025 (13)	−0.0101 (13)	0.0016 (13)
C7	0.0149 (15)	0.0137 (15)	0.0115 (15)	−0.0027 (12)	−0.0026 (12)	0.0025 (12)
C8	0.0083 (15)	0.0165 (16)	0.0168 (16)	−0.0032 (11)	−0.0078 (12)	0.0058 (12)
C9	0.0081 (15)	0.0168 (16)	0.0181 (16)	−0.0001 (11)	−0.0017 (12)	0.0028 (12)
C10	0.0150 (16)	0.0167 (16)	0.0179 (16)	0.0014 (12)	0.0002 (13)	0.0006 (13)
C11	0.0094 (15)	0.0127 (15)	0.0155 (16)	−0.0023 (11)	−0.0056 (12)	0.0041 (12)
C12	0.0117 (15)	0.0131 (15)	0.0166 (16)	−0.0001 (11)	−0.0014 (12)	0.0043 (12)
C13	0.0111 (15)	0.0207 (17)	0.0130 (16)	−0.0022 (12)	−0.0046 (12)	0.0012 (13)
C14	0.0113 (15)	0.0170 (16)	0.0156 (16)	0.0002 (12)	−0.0031 (12)	0.0030 (12)
C15	0.0064 (15)	0.0162 (16)	0.0262 (18)	0.0001 (11)	−0.0059 (12)	0.0066 (13)
C16	0.0075 (15)	0.0174 (15)	0.0244 (18)	0.0012 (12)	0.0055 (12)	0.0057 (13)
C17	0.0144 (16)	0.0143 (15)	0.0173 (17)	−0.0001 (12)	0.0009 (12)	0.0037 (12)
C18	0.0078 (15)	0.0116 (15)	0.0199 (17)	−0.0004 (11)	−0.0009 (12)	0.0021 (12)
C19	0.0110 (15)	0.0136 (15)	0.0187 (17)	−0.0002 (11)	0.0017 (12)	0.0010 (12)
C20	0.0072 (15)	0.0147 (16)	0.0245 (18)	0.0002 (11)	−0.0023 (13)	0.0036 (13)
O1W	0.0463 (18)	0.0461 (17)	0.0503 (18)	0.0009 (13)	0.0187 (14)	−0.0066 (14)

Geometric parameters (Å, º)

O1—N3	1.235 (3)	C3—H3B	0.99
O2—N3	1.240 (3)	C4—H4A	0.99
O3—N4	1.234 (3)	C4—H4B	0.99
O4—N4	1.234 (3)	C5—C6	1.531 (4)
O5—C13	1.238 (3)	C5—H5A	0.99
O6—C13	1.286 (3)	C5—H5B	0.99
O7—N5	1.227 (3)	C6—H6A	0.99
O8—N5	1.225 (3)	C6—H6B	0.99
O9—N6	1.229 (3)	C7—C8	1.383 (4)
O10—N6	1.221 (3)	C7—C12	1.385 (4)
O11—C20	1.234 (3)	C8—C9	1.375 (4)
O12—C20	1.283 (3)	C8—H8	0.95
N1—C4	1.491 (3)	C9—C10	1.387 (4)
N1—C5	1.497 (3)	C10—C11	1.395 (4)
N1—C1	1.497 (3)	C10—H10	0.95
N1—H1N1	0.94 (1)	C11—C12	1.390 (4)
N2—C3	1.487 (3)	C11—C13	1.521 (4)
N2—C6	1.488 (4)	C12—H12	0.95
N2—C2	1.490 (3)	C14—C19	1.387 (4)
N2—H1N2	0.94 (1)	C14—C15	1.395 (4)
N3—C7	1.473 (3)	C15—C16	1.367 (4)
N4—C9	1.482 (3)	C15—H15	0.95
N5—C14	1.473 (4)	C16—C17	1.397 (4)
N6—C16	1.482 (3)	C17—C18	1.398 (4)
C1—C2	1.538 (4)	C17—H17	0.95
C1—H1A	0.99	C18—C19	1.390 (4)
C1—H1B	0.99	C18—C20	1.529 (4)
C2—H2A	0.99	C19—H19	0.95
C2—H2B	0.99	O1W—H1W1	0.90 (1)
C3—C4	1.539 (4)	O1W—H2W1	0.91 (1)
C3—H3A	0.99
C4—N1—C5	109.6 (2)	C6—C5—H5B	109.9
C4—N1—C1	109.8 (2)	H5A—C5—H5B	108.3
C5—N1—C1	109.3 (2)	N2—C6—C5	108.7 (2)
C4—N1—H1N1	109 (2)	N2—C6—H6A	110.0
C5—N1—H1N1	111 (2)	C5—C6—H6A	110.0
C1—N1—H1N1	107 (2)	N2—C6—H6B	110.0
C3—N2—C6	110.0 (2)	C5—C6—H6B	110.0
C3—N2—C2	109.8 (2)	H6A—C6—H6B	108.3
C6—N2—C2	109.4 (2)	C8—C7—C12	122.6 (3)
C3—N2—H1N2	108 (3)	C8—C7—N3	118.5 (2)
C6—N2—H1N2	108 (3)	C12—C7—N3	118.8 (2)
C2—N2—H1N2	112 (3)	C9—C8—C7	116.6 (2)
O1—N3—O2	123.9 (2)	C9—C8—H8	121.7
O1—N3—C7	117.9 (2)	C7—C8—H8	121.7
O2—N3—C7	118.1 (2)	C8—C9—C10	123.1 (3)
O4—N4—O3	124.1 (2)	C8—C9—N4	118.6 (2)
O4—N4—C9	118.1 (2)	C10—C9—N4	118.3 (2)
O3—N4—C9	117.7 (2)	C9—C10—C11	118.8 (3)
O8—N5—O7	124.5 (3)	C9—C10—H10	120.6
O8—N5—C14	118.5 (2)	C11—C10—H10	120.6
O7—N5—C14	117.0 (2)	C12—C11—C10	119.5 (2)
O10—N6—O9	124.0 (2)	C12—C11—C13	120.3 (2)
O10—N6—C16	118.3 (2)	C10—C11—C13	120.1 (3)
O9—N6—C16	117.7 (3)	C7—C12—C11	119.3 (2)
N1—C1—C2	108.4 (2)	C7—C12—H12	120.4
N1—C1—H1A	110.0	C11—C12—H12	120.4
C2—C1—H1A	110.0	O5—C13—O6	125.6 (3)
N1—C1—H1B	110.0	O5—C13—C11	120.0 (2)
C2—C1—H1B	110.0	O6—C13—C11	114.3 (2)
H1A—C1—H1B	108.4	C19—C14—C15	122.3 (3)
N2—C2—C1	108.7 (2)	C19—C14—N5	119.3 (2)
N2—C2—H2A	109.9	C15—C14—N5	118.4 (2)
C1—C2—H2A	109.9	C16—C15—C14	116.7 (3)
N2—C2—H2B	109.9	C16—C15—H15	121.7
C1—C2—H2B	109.9	C14—C15—H15	121.7
H2A—C2—H2B	108.3	C15—C16—C17	123.4 (2)
N2—C3—C4	108.8 (2)	C15—C16—N6	118.5 (2)
N2—C3—H3A	109.9	C17—C16—N6	118.1 (3)
C4—C3—H3A	109.9	C16—C17—C18	118.6 (3)
N2—C3—H3B	109.9	C16—C17—H17	120.7
C4—C3—H3B	109.9	C18—C17—H17	120.7
H3A—C3—H3B	108.3	C19—C18—C17	119.5 (2)
N1—C4—C3	108.4 (2)	C19—C18—C20	120.4 (2)
N1—C4—H4A	110.0	C17—C18—C20	120.1 (2)
C3—C4—H4A	110.0	C14—C19—C18	119.6 (2)
N1—C4—H4B	110.0	C14—C19—H19	120.2
C3—C4—H4B	110.0	C18—C19—H19	120.2
H4A—C4—H4B	108.4	O11—C20—O12	125.4 (3)
N1—C5—C6	108.7 (2)	O11—C20—C18	118.9 (2)
N1—C5—H5A	109.9	O12—C20—C18	115.7 (2)
C6—C5—H5A	109.9	H1W1—O1W—H2W1	102.0 (14)
N1—C5—H5B	109.9
C4—N1—C1—C2	−52.7 (3)	N3—C7—C12—C11	179.2 (2)
C5—N1—C1—C2	67.6 (3)	C10—C11—C12—C7	2.7 (4)
C3—N2—C2—C1	67.8 (3)	C13—C11—C12—C7	179.9 (2)
C6—N2—C2—C1	−53.0 (3)	C12—C11—C13—O5	160.3 (3)
N1—C1—C2—N2	−12.7 (3)	C10—C11—C13—O5	−22.4 (4)
C6—N2—C3—C4	67.6 (3)	C12—C11—C13—O6	−20.5 (4)
C2—N2—C3—C4	−52.8 (3)	C10—C11—C13—O6	156.8 (2)
C5—N1—C4—C3	−52.5 (3)	O8—N5—C14—C19	167.2 (3)
C1—N1—C4—C3	67.6 (3)	O7—N5—C14—C19	−14.3 (4)
N2—C3—C4—N1	−12.6 (3)	O8—N5—C14—C15	−11.8 (4)
C4—N1—C5—C6	67.9 (3)	O7—N5—C14—C15	166.7 (3)
C1—N1—C5—C6	−52.6 (3)	C19—C14—C15—C16	1.7 (4)
C3—N2—C6—C5	−52.3 (3)	N5—C14—C15—C16	−179.4 (2)
C2—N2—C6—C5	68.3 (3)	C14—C15—C16—C17	−1.1 (4)
N1—C5—C6—N2	−13.0 (3)	C14—C15—C16—N6	−178.6 (2)
O1—N3—C7—C8	−169.4 (2)	O10—N6—C16—C15	172.4 (3)
O2—N3—C7—C8	10.7 (4)	O9—N6—C16—C15	−6.5 (4)
O1—N3—C7—C12	8.4 (4)	O10—N6—C16—C17	−5.2 (4)
O2—N3—C7—C12	−171.5 (2)	O9—N6—C16—C17	175.9 (3)
C12—C7—C8—C9	0.6 (4)	C15—C16—C17—C18	0.2 (4)
N3—C7—C8—C9	178.4 (2)	N6—C16—C17—C18	177.7 (2)
C7—C8—C9—C10	2.4 (4)	C16—C17—C18—C19	0.2 (4)
C7—C8—C9—N4	−177.3 (2)	C16—C17—C18—C20	−177.6 (2)
O4—N4—C9—C8	−173.6 (2)	C15—C14—C19—C18	−1.3 (4)
O3—N4—C9—C8	6.4 (4)	N5—C14—C19—C18	179.8 (2)
O4—N4—C9—C10	6.7 (4)	C17—C18—C19—C14	0.3 (4)
O3—N4—C9—C10	−173.3 (3)	C20—C18—C19—C14	178.2 (2)
C8—C9—C10—C11	−2.7 (4)	C19—C18—C20—O11	−179.5 (3)
N4—C9—C10—C11	177.0 (2)	C17—C18—C20—O11	−1.7 (4)
C9—C10—C11—C12	0.1 (4)	C19—C18—C20—O12	0.1 (4)
C9—C10—C11—C13	−177.2 (2)	C17—C18—C20—O12	178.0 (2)
C8—C7—C12—C11	−3.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O11^i	0.94 (1)	2.56 (2)	3.119 (3)	118 (2)
N1—H1N1···O12^i	0.94 (1)	1.72 (2)	2.658 (3)	174 (3)
N2—H1N2···O6^ii	0.94 (1)	1.63 (3)	2.566 (3)	174 (4)
O1W—H1W1···O5^iii	0.90 (1)	1.97 (3)	2.823 (3)	156 (3)
O1W—H2W1···O11	0.91 (1)	1.95 (3)	2.839 (3)	168 (3)
C1—H1B···O1^iv	0.99	2.50	3.332 (4)	141
C3—H3A···O4	0.99	2.60	3.409 (3)	139
C3—H3B···O5^iii	0.99	2.43	3.306 (4)	148
C6—H6B···O2^v	0.99	2.51	3.397 (4)	149
C6—H6B···O7^v	0.99	2.54	3.189 (4)	123
C8—H8···O3^v	0.95	2.49	3.264 (3)	138
C17—H17···O1W	0.95	2.41	3.315 (4)	160

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