Monoprotonated [2.2.2]cryptand picrate monohydrate

The title compound, 4,7,13,16,21,24-hexa­oxa-1-azonia-10-aza­bicyclo­[8.8.8]hexa­cosane picrate monohydrate, C₁₈H₃₇N₂O₆⁺·C₆H₂N₃O₇⁻·H₂O, is a salt of [2.2.2]cryptand (4,7,13,16,21,24-hexa­oxa-1,10-diaza­bicyclo­[8.8.8]hexa­cosa­ne) with picric acid (2,4,6-trinitro­phenol). The monoprotonated cryptand cation encapsulates a water mol­ecule through N—H...O and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.131
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.855     0.984
            Tmin(prime) and Tmax expected:      0.980     0.984
            RR(prime) =      0.872
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1

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

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

4,7,13,16,21,24-hexaoxa-1-azonia-10-azabicyclo[8.8.8]hexacosane picrate monohydrate

Crystal data

C18H37N2O6^+·C6H2N3O7^−·H2O	F(000) = 1328.00
Mr = 623.61	Dx = 1.424 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 17071 reflections
a = 9.2633 (3) Å	θ = 3.1–30.0°
b = 19.2661 (6) Å	µ = 0.12 mm^−1
c = 16.3624 (5) Å	T = 150 K
β = 94.8805 (11)°	Block, light orange
V = 2909.57 (16) Å^3	0.17 × 0.16 × 0.14 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3809 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.067
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.855, Tmax = 0.984	k = −22→25
27944 measured reflections	l = −21→21
6652 independent reflections

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0486P)^2 + 0.9805P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.131	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.37 e Å^−3
6652 reflections	Δρmin = −0.36 e Å^−3
401 parameters

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	0.77296 (19)	0.52106 (10)	0.83919 (9)	0.0464 (5)
O2	0.6582 (2)	0.44969 (11)	0.95639 (11)	0.0607 (6)
O3	0.6790 (2)	0.49018 (11)	1.07753 (11)	0.0643 (7)
O4	1.05127 (18)	0.64775 (9)	1.16624 (9)	0.0373 (4)
O5	1.18712 (17)	0.69393 (8)	1.07946 (9)	0.0346 (4)
O6	1.0762 (2)	0.65528 (10)	0.78939 (10)	0.0492 (5)
O7	1.0162 (2)	0.54904 (10)	0.76017 (10)	0.0485 (5)
O8	0.54308 (16)	0.25531 (8)	0.66018 (9)	0.0291 (4)
O9	0.35637 (17)	0.20206 (8)	0.51844 (8)	0.0298 (4)
O10	0.74915 (17)	0.41107 (7)	0.52728 (8)	0.0279 (4)
O11	0.55384 (16)	0.38291 (8)	0.38443 (8)	0.0278 (4)
O12	0.30244 (17)	0.40292 (9)	0.67876 (9)	0.0343 (4)
O13	0.13705 (16)	0.35294 (8)	0.54391 (8)	0.0284 (4)
O14	0.44094 (19)	0.39776 (10)	0.53867 (9)	0.0344 (4)
N1	0.7108 (2)	0.49058 (10)	1.00681 (11)	0.0300 (4)
N2	1.0875 (2)	0.65521 (9)	1.09566 (10)	0.0255 (4)
N3	1.0239 (2)	0.59899 (11)	0.80699 (11)	0.0342 (5)
N4	0.5989 (2)	0.41072 (9)	0.68611 (10)	0.0236 (4)
N5	0.27304 (19)	0.30947 (9)	0.38879 (10)	0.0251 (4)
C1	0.8487 (2)	0.54625 (12)	0.89796 (13)	0.0276 (5)
C2	0.8213 (2)	0.53840 (11)	0.98380 (13)	0.0240 (5)
C3	0.8978 (2)	0.57320 (11)	1.04679 (12)	0.0243 (5)
H3	0.8757	0.5665	1.1006	0.029*
C4	1.0079 (2)	0.61823 (11)	1.02986 (12)	0.0227 (5)
C5	1.0459 (2)	0.62718 (11)	0.95026 (12)	0.0250 (5)
H5	1.1205	0.6573	0.9395	0.030*
C6	0.9725 (2)	0.59117 (11)	0.88815 (12)	0.0257 (5)
C7	0.6165 (3)	0.35071 (11)	0.74403 (12)	0.0280 (5)
H7B	0.5247	0.3415	0.7664	0.034*
H7A	0.6865	0.3628	0.7893	0.034*
C8	0.6661 (2)	0.28606 (12)	0.70310 (14)	0.0313 (5)
H8A	0.7377	0.2976	0.6653	0.038*
H8B	0.7096	0.2541	0.7438	0.038*
C9	0.5804 (3)	0.19835 (12)	0.61064 (13)	0.0308 (5)
H9B	0.6413	0.1660	0.6433	0.037*
H9A	0.6339	0.2148	0.5660	0.037*
C10	0.4439 (3)	0.16258 (12)	0.57672 (13)	0.0315 (5)
H10A	0.4700	0.1194	0.5512	0.038*
H10B	0.3869	0.1510	0.6219	0.038*
C11	0.4121 (3)	0.20478 (13)	0.44022 (13)	0.0324 (5)
H11B	0.4385	0.1585	0.4234	0.039*
H11A	0.4980	0.2337	0.4428	0.039*
C12	0.2975 (3)	0.23436 (11)	0.37928 (13)	0.0297 (5)
H12A	0.3252	0.2257	0.3243	0.036*
H12B	0.2070	0.2101	0.3848	0.036*
C13	0.7463 (2)	0.43803 (12)	0.66877 (12)	0.0270 (5)
H13A	0.7747	0.4740	0.7084	0.032*
H13B	0.8163	0.4006	0.6766	0.032*
C14	0.7527 (3)	0.46717 (11)	0.58383 (12)	0.0292 (5)
H14A	0.6709	0.4978	0.5706	0.035*
H14B	0.8411	0.4937	0.5809	0.035*
C15	0.7697 (3)	0.43410 (12)	0.44615 (12)	0.0310 (5)
H15B	0.8722	0.4403	0.4403	0.037*
H15A	0.7217	0.4784	0.4359	0.037*
C16	0.7082 (3)	0.38133 (13)	0.38558 (13)	0.0318 (5)
H16A	0.7376	0.3919	0.3314	0.038*
H16B	0.7440	0.3355	0.4012	0.038*
C17	0.4844 (3)	0.34652 (12)	0.31610 (12)	0.0304 (5)
H17B	0.5173	0.2987	0.3168	0.037*
H17A	0.5096	0.3677	0.2655	0.037*
C18	0.3226 (3)	0.34849 (12)	0.31983 (13)	0.0316 (5)
H18A	0.2921	0.3964	0.3239	0.038*
H18B	0.2764	0.3297	0.2691	0.038*
C19	0.5107 (3)	0.46852 (12)	0.71860 (13)	0.0299 (5)
H19A	0.5643	0.4884	0.7665	0.036*
H19B	0.4982	0.5046	0.6773	0.036*
C20	0.3641 (3)	0.44628 (13)	0.74158 (13)	0.0312 (5)
H20A	0.3733	0.4214	0.7933	0.037*
H20B	0.3030	0.4866	0.7475	0.037*
C21	0.1547 (2)	0.38701 (14)	0.68409 (14)	0.0343 (6)
H21B	0.0952	0.4275	0.6706	0.041*
H21A	0.1387	0.3724	0.7393	0.041*
C22	0.1161 (3)	0.32961 (13)	0.62449 (13)	0.0347 (6)
H22A	0.1767	0.2895	0.6379	0.042*
H22B	0.0158	0.3162	0.6276	0.042*
C23	0.0788 (2)	0.30457 (12)	0.48371 (13)	0.0288 (5)
H23B	−0.0260	0.3037	0.4832	0.035*
H23A	0.1149	0.2584	0.4974	0.035*
C24	0.1214 (2)	0.32502 (12)	0.40028 (13)	0.0301 (5)
H24A	0.0598	0.3007	0.3587	0.036*
H24B	0.1050	0.3744	0.3925	0.036*
H4N	0.544 (3)	0.3974 (14)	0.6354 (16)	0.054 (8)*
H14C	0.362 (3)	0.3763 (16)	0.5414 (19)	0.077 (12)*
H14D	0.471 (4)	0.3842 (17)	0.4927 (14)	0.083 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0372 (11)	0.0700 (13)	0.0313 (9)	−0.0171 (10)	−0.0019 (7)	−0.0157 (9)
O2	0.0672 (15)	0.0661 (14)	0.0487 (11)	−0.0405 (12)	0.0051 (10)	−0.0131 (10)
O3	0.0701 (15)	0.0795 (15)	0.0478 (11)	−0.0419 (12)	0.0321 (10)	−0.0203 (10)
O4	0.0311 (10)	0.0569 (11)	0.0241 (8)	−0.0037 (8)	0.0034 (7)	−0.0078 (7)
O5	0.0298 (10)	0.0350 (10)	0.0381 (9)	−0.0092 (8)	−0.0025 (7)	−0.0008 (7)
O6	0.0533 (13)	0.0622 (13)	0.0319 (9)	−0.0237 (10)	0.0024 (8)	0.0083 (8)
O7	0.0553 (13)	0.0575 (13)	0.0341 (9)	−0.0021 (10)	0.0123 (8)	−0.0137 (9)
O8	0.0232 (9)	0.0312 (9)	0.0324 (8)	0.0025 (7)	0.0005 (6)	−0.0016 (7)
O9	0.0282 (9)	0.0342 (9)	0.0270 (8)	0.0049 (7)	0.0026 (6)	0.0017 (6)
O10	0.0320 (9)	0.0279 (8)	0.0240 (8)	−0.0018 (7)	0.0040 (6)	−0.0014 (6)
O11	0.0265 (9)	0.0347 (9)	0.0225 (7)	−0.0012 (7)	0.0038 (6)	−0.0049 (6)
O12	0.0231 (9)	0.0512 (11)	0.0290 (8)	−0.0048 (8)	0.0056 (6)	−0.0132 (7)
O13	0.0266 (9)	0.0311 (9)	0.0276 (8)	−0.0064 (7)	0.0027 (6)	−0.0034 (6)
O14	0.0262 (10)	0.0534 (11)	0.0237 (9)	−0.0062 (9)	0.0020 (7)	−0.0053 (7)
N1	0.0253 (11)	0.0298 (11)	0.0351 (11)	−0.0019 (9)	0.0037 (8)	−0.0044 (8)
N2	0.0203 (10)	0.0287 (10)	0.0272 (10)	0.0019 (8)	−0.0002 (7)	−0.0022 (8)
N3	0.0277 (11)	0.0496 (14)	0.0250 (10)	−0.0035 (10)	−0.0002 (8)	−0.0006 (9)
N4	0.0214 (10)	0.0275 (10)	0.0216 (9)	−0.0014 (8)	−0.0011 (7)	0.0001 (7)
N5	0.0233 (10)	0.0261 (10)	0.0256 (9)	−0.0002 (8)	0.0003 (7)	−0.0004 (7)
C1	0.0221 (12)	0.0334 (13)	0.0269 (12)	0.0025 (10)	−0.0002 (9)	−0.0040 (9)
C2	0.0157 (11)	0.0256 (12)	0.0305 (11)	−0.0004 (9)	0.0012 (8)	−0.0031 (9)
C3	0.0225 (12)	0.0255 (12)	0.0251 (11)	0.0073 (9)	0.0027 (9)	−0.0008 (9)
C4	0.0196 (11)	0.0258 (12)	0.0222 (10)	0.0012 (9)	−0.0019 (8)	−0.0034 (8)
C5	0.0219 (12)	0.0235 (11)	0.0290 (11)	0.0030 (9)	−0.0004 (9)	0.0015 (9)
C6	0.0257 (12)	0.0314 (12)	0.0201 (11)	0.0022 (10)	0.0019 (9)	0.0004 (9)
C7	0.0266 (13)	0.0343 (13)	0.0230 (11)	0.0000 (10)	0.0002 (9)	0.0064 (9)
C8	0.0232 (12)	0.0311 (13)	0.0392 (13)	−0.0015 (10)	0.0003 (10)	0.0048 (10)
C9	0.0296 (13)	0.0314 (13)	0.0316 (12)	0.0073 (10)	0.0045 (10)	0.0019 (9)
C10	0.0355 (14)	0.0278 (13)	0.0308 (12)	0.0037 (10)	0.0014 (10)	0.0054 (9)
C11	0.0310 (14)	0.0374 (14)	0.0293 (12)	0.0057 (11)	0.0057 (10)	0.0003 (10)
C12	0.0323 (13)	0.0284 (12)	0.0281 (12)	−0.0001 (10)	0.0020 (9)	−0.0050 (9)
C13	0.0222 (12)	0.0311 (12)	0.0272 (11)	−0.0069 (10)	−0.0014 (9)	−0.0023 (9)
C14	0.0312 (13)	0.0270 (12)	0.0294 (12)	−0.0072 (10)	0.0026 (9)	−0.0032 (9)
C15	0.0273 (13)	0.0387 (14)	0.0279 (12)	−0.0046 (11)	0.0079 (9)	0.0011 (10)
C16	0.0286 (14)	0.0399 (14)	0.0282 (11)	0.0003 (11)	0.0105 (9)	−0.0016 (10)
C17	0.0375 (14)	0.0325 (13)	0.0219 (11)	−0.0060 (11)	0.0059 (9)	−0.0040 (9)
C18	0.0399 (15)	0.0317 (13)	0.0219 (11)	−0.0028 (11)	−0.0040 (9)	−0.0006 (9)
C19	0.0312 (13)	0.0290 (12)	0.0280 (12)	0.0006 (10)	−0.0051 (9)	−0.0054 (9)
C20	0.0304 (14)	0.0370 (14)	0.0260 (12)	0.0027 (11)	0.0008 (9)	−0.0067 (10)
C21	0.0206 (12)	0.0520 (16)	0.0318 (12)	−0.0029 (11)	0.0111 (9)	−0.0049 (11)
C22	0.0283 (14)	0.0433 (15)	0.0336 (13)	−0.0082 (11)	0.0092 (10)	−0.0011 (11)
C23	0.0198 (12)	0.0292 (13)	0.0366 (12)	−0.0035 (10)	−0.0031 (9)	−0.0046 (9)
C24	0.0272 (13)	0.0291 (12)	0.0329 (12)	−0.0010 (10)	−0.0043 (9)	−0.0024 (9)

Geometric parameters (Å, º)

O1—C1	1.240 (3)	C8—H8A	0.9700
O2—N1	1.213 (2)	C8—H8B	0.9700
O3—N1	1.218 (2)	C9—C10	1.504 (3)
O4—N2	1.238 (2)	C9—H9B	0.9700
O5—N2	1.233 (2)	C9—H9A	0.9700
O6—N3	1.232 (3)	C10—H10A	0.9700
O7—N3	1.228 (3)	C10—H10B	0.9700
O8—C8	1.416 (3)	C11—C12	1.505 (3)
O8—C9	1.424 (3)	C11—H11B	0.9700
O9—C10	1.419 (3)	C11—H11A	0.9700
O9—C11	1.421 (2)	C12—H12A	0.9700
O10—C14	1.422 (2)	C12—H12B	0.9700
O10—C15	1.428 (2)	C13—C14	1.505 (3)
O11—C17	1.426 (2)	C13—H13A	0.9700
O11—C16	1.429 (3)	C13—H13B	0.9700
O12—C20	1.407 (3)	C14—H14A	0.9700
O12—C21	1.413 (3)	C14—H14B	0.9700
O13—C22	1.422 (2)	C15—C16	1.498 (3)
O13—C23	1.428 (2)	C15—H15B	0.9700
O14—H14C	0.844 (18)	C15—H15A	0.9700
O14—H14D	0.863 (18)	C16—H16A	0.9700
N1—C2	1.451 (3)	C16—H16B	0.9700
N2—C4	1.441 (3)	C17—C18	1.506 (3)
N3—C6	1.456 (3)	C17—H17B	0.9700
N4—C7	1.495 (3)	C17—H17A	0.9700
N4—C19	1.504 (3)	C18—H18A	0.9700
N4—C13	1.513 (3)	C18—H18B	0.9700
N4—H4N	0.97 (3)	C19—C20	1.503 (3)
N5—C18	1.462 (3)	C19—H19A	0.9700
N5—C24	1.464 (3)	C19—H19B	0.9700
N5—C12	1.475 (3)	C20—H20A	0.9700
C1—C2	1.456 (3)	C20—H20B	0.9700
C1—C6	1.456 (3)	C21—C22	1.497 (3)
C2—C3	1.375 (3)	C21—H21B	0.9700
C3—C4	1.385 (3)	C21—H21A	0.9700
C3—H3	0.9300	C22—H22A	0.9700
C4—C5	1.389 (3)	C22—H22B	0.9700
C5—C6	1.364 (3)	C23—C24	1.505 (3)
C5—H5	0.9300	C23—H23B	0.9700
C7—C8	1.505 (3)	C23—H23A	0.9700
C7—H7B	0.9700	C24—H24A	0.9700
C7—H7A	0.9700	C24—H24B	0.9700
C8—O8—C9	112.36 (17)	N5—C12—H12B	108.7
C10—O9—C11	113.24 (17)	C11—C12—H12B	108.7
C14—O10—C15	111.79 (16)	H12A—C12—H12B	107.6
C17—O11—C16	112.60 (16)	C14—C13—N4	114.22 (18)
C20—O12—C21	114.75 (16)	C14—C13—H13A	108.7
C22—O13—C23	111.09 (16)	N4—C13—H13A	108.7
H14C—O14—H14D	104 (3)	C14—C13—H13B	108.7
O2—N1—O3	121.8 (2)	N4—C13—H13B	108.7
O2—N1—C2	119.19 (18)	H13A—C13—H13B	107.6
O3—N1—C2	118.92 (18)	O10—C14—C13	108.47 (17)
O5—N2—O4	122.55 (18)	O10—C14—H14A	110.0
O5—N2—C4	118.91 (17)	C13—C14—H14A	110.0
O4—N2—C4	118.52 (18)	O10—C14—H14B	110.0
O7—N3—O6	123.2 (2)	C13—C14—H14B	110.0
O7—N3—C6	118.8 (2)	H14A—C14—H14B	108.4
O6—N3—C6	118.02 (19)	O10—C15—C16	109.32 (18)
C7—N4—C19	112.43 (16)	O10—C15—H15B	109.8
C7—N4—C13	109.66 (17)	C16—C15—H15B	109.8
C19—N4—C13	109.55 (17)	O10—C15—H15A	109.8
C7—N4—H4N	111.0 (16)	C16—C15—H15A	109.8
C19—N4—H4N	103.8 (16)	H15B—C15—H15A	108.3
C13—N4—H4N	110.3 (16)	O11—C16—C15	108.53 (18)
C18—N5—C24	111.19 (17)	O11—C16—H16A	110.0
C18—N5—C12	111.23 (17)	C15—C16—H16A	110.0
C24—N5—C12	111.83 (17)	O11—C16—H16B	110.0
O1—C1—C2	125.0 (2)	C15—C16—H16B	110.0
O1—C1—C6	123.1 (2)	H16A—C16—H16B	108.4
C2—C1—C6	111.80 (18)	O11—C17—C18	109.89 (17)
C3—C2—N1	116.45 (19)	O11—C17—H17B	109.7
C3—C2—C1	123.5 (2)	C18—C17—H17B	109.7
N1—C2—C1	120.06 (18)	O11—C17—H17A	109.7
C2—C3—C4	119.80 (19)	C18—C17—H17A	109.7
C2—C3—H3	120.1	H17B—C17—H17A	108.2
C4—C3—H3	120.1	N5—C18—C17	113.40 (18)
C3—C4—C5	121.02 (19)	N5—C18—H18A	108.9
C3—C4—N2	119.95 (18)	C17—C18—H18A	108.9
C5—C4—N2	119.01 (19)	N5—C18—H18B	108.9
C6—C5—C4	119.0 (2)	C17—C18—H18B	108.9
C6—C5—H5	120.5	H18A—C18—H18B	107.7
C4—C5—H5	120.5	C20—C19—N4	114.00 (18)
C5—C6—N3	116.5 (2)	C20—C19—H19A	108.8
C5—C6—C1	124.60 (19)	N4—C19—H19A	108.8
N3—C6—C1	118.92 (18)	C20—C19—H19B	108.8
N4—C7—C8	112.27 (17)	N4—C19—H19B	108.8
N4—C7—H7B	109.2	H19A—C19—H19B	107.6
C8—C7—H7B	109.2	O12—C20—C19	107.80 (17)
N4—C7—H7A	109.2	O12—C20—H20A	110.1
C8—C7—H7A	109.2	C19—C20—H20A	110.1
H7B—C7—H7A	107.9	O12—C20—H20B	110.1
O8—C8—C7	107.67 (18)	C19—C20—H20B	110.1
O8—C8—H8A	110.2	H20A—C20—H20B	108.5
C7—C8—H8A	110.2	O12—C21—C22	107.39 (18)
O8—C8—H8B	110.2	O12—C21—H21B	110.2
C7—C8—H8B	110.2	C22—C21—H21B	110.2
H8A—C8—H8B	108.5	O12—C21—H21A	110.2
O8—C9—C10	109.02 (19)	C22—C21—H21A	110.2
O8—C9—H9B	109.9	H21B—C21—H21A	108.5
C10—C9—H9B	109.9	O13—C22—C21	109.06 (19)
O8—C9—H9A	109.9	O13—C22—H22A	109.9
C10—C9—H9A	109.9	C21—C22—H22A	109.9
H9B—C9—H9A	108.3	O13—C22—H22B	109.9
O9—C10—C9	114.62 (18)	C21—C22—H22B	109.9
O9—C10—H10A	108.6	H22A—C22—H22B	108.3
C9—C10—H10A	108.6	O13—C23—C24	109.97 (18)
O9—C10—H10B	108.6	O13—C23—H23B	109.7
C9—C10—H10B	108.6	C24—C23—H23B	109.7
H10A—C10—H10B	107.6	O13—C23—H23A	109.7
O9—C11—C12	108.73 (18)	C24—C23—H23A	109.7
O9—C11—H11B	109.9	H23B—C23—H23A	108.2
C12—C11—H11B	109.9	N5—C24—C23	113.06 (18)
O9—C11—H11A	109.9	N5—C24—H24A	109.0
C12—C11—H11A	109.9	C23—C24—H24A	109.0
H11B—C11—H11A	108.3	N5—C24—H24B	109.0
N5—C12—C11	114.04 (18)	C23—C24—H24B	109.0
N5—C12—H12A	108.7	H24A—C24—H24B	107.8
C11—C12—H12A	108.7
O2—N1—C2—C3	−167.0 (2)	N4—C7—C8—O8	−80.5 (2)
O3—N1—C2—C3	9.2 (3)	C8—O8—C9—C10	172.15 (17)
O2—N1—C2—C1	11.6 (3)	C11—O9—C10—C9	75.6 (2)
O3—N1—C2—C1	−172.3 (2)	O8—C9—C10—O9	68.2 (2)
O1—C1—C2—C3	−172.6 (2)	C10—O9—C11—C12	168.19 (18)
C6—C1—C2—C3	4.1 (3)	C18—N5—C12—C11	111.3 (2)
O1—C1—C2—N1	9.0 (3)	C24—N5—C12—C11	−123.8 (2)
C6—C1—C2—N1	−174.36 (18)	O9—C11—C12—N5	72.5 (2)
N1—C2—C3—C4	178.16 (19)	C7—N4—C13—C14	147.63 (18)
C1—C2—C3—C4	−0.3 (3)	C19—N4—C13—C14	−88.5 (2)
C2—C3—C4—C5	−2.2 (3)	C15—O10—C14—C13	−174.05 (18)
C2—C3—C4—N2	179.49 (19)	N4—C13—C14—O10	−73.6 (2)
O5—N2—C4—C3	178.48 (19)	C14—O10—C15—C16	−157.66 (19)
O4—N2—C4—C3	−2.8 (3)	C17—O11—C16—C15	166.48 (18)
O5—N2—C4—C5	0.2 (3)	O10—C15—C16—O11	70.5 (2)
O4—N2—C4—C5	178.85 (19)	C16—O11—C17—C18	178.44 (18)
C3—C4—C5—C6	0.4 (3)	C24—N5—C18—C17	167.72 (18)
N2—C4—C5—C6	178.75 (19)	C12—N5—C18—C17	−66.9 (2)
C4—C5—C6—N3	−175.83 (19)	O11—C17—C18—N5	−67.0 (2)
C4—C5—C6—C1	4.0 (3)	C7—N4—C19—C20	−55.2 (2)
O7—N3—C6—C5	145.6 (2)	C13—N4—C19—C20	−177.36 (17)
O6—N3—C6—C5	−32.8 (3)	C21—O12—C20—C19	−169.75 (19)
O7—N3—C6—C1	−34.2 (3)	N4—C19—C20—O12	−44.2 (2)
O6—N3—C6—C1	147.4 (2)	C20—O12—C21—C22	−168.24 (19)
O1—C1—C6—C5	170.7 (2)	C23—O13—C22—C21	−170.12 (18)
C2—C1—C6—C5	−6.0 (3)	O12—C21—C22—O13	−61.3 (2)
O1—C1—C6—N3	−9.4 (3)	C22—O13—C23—C24	−171.69 (18)
C2—C1—C6—N3	173.85 (19)	C18—N5—C24—C23	−162.17 (18)
C19—N4—C7—C8	163.72 (18)	C12—N5—C24—C23	72.8 (2)
C13—N4—C7—C8	−74.2 (2)	O13—C23—C24—N5	75.1 (2)
C9—O8—C8—C7	172.63 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O14	0.97 (3)	1.78 (3)	2.725 (2)	164 (2)
O14—H14C···O13	0.85 (3)	2.14 (3)	2.953 (2)	163 (3)
O14—H14D···O11	0.86 (3)	1.99 (3)	2.827 (2)	163 (3)
C7—H7A···O4^i	0.97	2.48	3.295 (3)	141
C7—H7A···O5^i	0.97	2.60	3.391 (3)	139
C13—H13A···O1	0.97	2.33	3.206 (3)	151
C19—H19A···O1	0.97	2.27	3.163 (3)	152
C19—H19B···O11^ii	0.97	2.42	3.350 (3)	160
C21—H21A···O4^iii	0.97	2.47	3.299 (3)	143
C23—H23A···O9	0.97	2.48	3.254 (3)	136

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