Diethyl­enetriammonium oxonium naphthalene-1,6-disulfonate 3.5-hydrate

The title complex, C₄H₁₆N₃³⁺·H₃O⁺·2C₁₀H₆O₆S₂²⁻·3.5H₂O, comprises one diethyl­enetriammonium trication, one oxonium cation, two naphthalene-1,6-disulfonate dianions and three-and-a-half water mol­ecules. The oxonium cation donates a proton to each of three acceptors, forming strong hydrogen bonds, O—H...O [2.476 (4), 2.473 (4) and 2.503 (4) Å]. O—H...O and N—H...O hydrogen bonds link the title complex into layers parallel to the (010) plane.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.147
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S3
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O14
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1A    ..  H17A    ..       2.12 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H14A   ..  H16A    ..       2.13 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H3 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
              H2 O

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Diethylenetriammonium oxonium naphthalene-1,6-disulfonate 3.5-hydrate

Crystal data

C4H16N3^3+·H3O^+·2C10H6O6S2^2^−·3.5H2O	F(000) = 3192
Mr = 760.85	Dx = 1.557 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1109 reflections
a = 25.392 (2) Å	θ = 2.2–18.1°
b = 13.1747 (11) Å	µ = 0.37 mm^−1
c = 19.5144 (16) Å	T = 273 K
β = 96.011 (2)°	Block, colourless
V = 6492.2 (9) Å^3	0.38 × 0.32 × 0.29 mm
Z = 8

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5848 independent reflections
Radiation source: fine-focus sealed tube	4933 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→30
Tmin = 0.868, Tmax = 0.898	k = −15→15
16963 measured reflections	l = −23→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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0722P)^2 + 13.0061P] where P = (Fo^2 + 2Fc^2)/3
5848 reflections	(Δ/σ)max < 0.001
464 parameters	Δρmax = 0.81 e Å^−3
18 restraints	Δρmin = −0.56 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)
S1	0.40830 (3)	0.10608 (6)	0.10970 (4)	0.0382 (2)
S2	0.12613 (3)	0.10420 (5)	0.09027 (4)	0.0341 (2)
S3	0.64966 (3)	0.09647 (6)	0.13071 (4)	0.0405 (2)
S4	0.93233 (3)	0.11539 (6)	0.17116 (4)	0.0375 (2)
O1	0.42436 (10)	0.2073 (2)	0.13120 (17)	0.0788 (9)
O2	0.41719 (9)	0.0362 (2)	0.16587 (14)	0.0648 (8)
O3	0.43211 (10)	0.0771 (3)	0.04985 (14)	0.0959 (12)
O4	0.12979 (9)	0.19579 (19)	0.13149 (13)	0.0566 (6)
O5	0.13909 (8)	0.01324 (18)	0.13092 (12)	0.0482 (6)
O6	0.07486 (8)	0.09290 (18)	0.05040 (12)	0.0482 (6)
O7	0.59964 (9)	0.10221 (19)	0.09032 (13)	0.0566 (7)
O8	0.65854 (11)	−0.0051 (2)	0.15861 (17)	0.0849 (10)
O9	0.65743 (11)	0.1727 (3)	0.18350 (15)	0.0815 (10)
O10	0.94052 (9)	0.20999 (19)	0.20950 (14)	0.0625 (7)
O11	0.94339 (9)	0.02594 (19)	0.21188 (13)	0.0578 (7)
O12	0.96096 (9)	0.11696 (19)	0.11091 (13)	0.0564 (7)
O13	0.5000	−0.0492 (2)	0.2500	0.0511 (8)
O14	0.29509 (11)	−0.1315 (2)	0.26049 (14)	0.0655 (7)
O15	0.36817 (11)	−0.1417 (2)	0.18640 (18)	0.0719 (8)
O16	0.20286 (11)	−0.1336 (2)	0.20483 (19)	0.0786 (9)
O17	0.56151 (18)	0.2518 (3)	0.22664 (18)	0.1184 (16)
N1	0.53627 (9)	0.42397 (19)	0.15496 (12)	0.0375 (6)
H1A	0.5467	0.3721	0.1823	0.056*
H1B	0.5182	0.4679	0.1780	0.056*
H1C	0.5645	0.4547	0.1411	0.056*
N2	0.49251 (9)	0.25535 (17)	0.00471 (12)	0.0337 (5)
H2A	0.4769	0.3024	−0.0241	0.040*
H2B	0.4671	0.2260	0.0267	0.040*
N3	0.46336 (10)	0.1931 (2)	−0.15177 (12)	0.0419 (6)
H3A	0.4344	0.2284	−0.1450	0.063*
H3B	0.4568	0.1545	−0.1891	0.063*
H3C	0.4897	0.2357	−0.1576	0.063*
C1	0.50220 (12)	0.3863 (2)	0.09451 (16)	0.0375 (7)
H1D	0.4921	0.4425	0.0638	0.045*
H1E	0.4702	0.3573	0.1094	0.045*
C2	0.53052 (11)	0.3068 (2)	0.05623 (15)	0.0388 (7)
H2C	0.5583	0.3386	0.0332	0.047*
H2D	0.5468	0.2572	0.0886	0.047*
C3	0.51709 (12)	0.1765 (2)	−0.03679 (15)	0.0398 (7)
H3D	0.5328	0.1244	−0.0060	0.048*
H3E	0.5454	0.2076	−0.0593	0.048*
C4	0.47857 (14)	0.1274 (2)	−0.09066 (16)	0.0435 (8)
H4A	0.4942	0.0653	−0.1060	0.052*
H4B	0.4468	0.1091	−0.0698	0.052*
C5	0.33905 (11)	0.11000 (19)	0.08725 (14)	0.0289 (6)
C6	0.30469 (11)	0.1063 (2)	0.13970 (14)	0.0302 (6)
H6	0.3184	0.1018	0.1857	0.036*
C7	0.25136 (11)	0.1092 (2)	0.12247 (14)	0.0301 (6)
H7	0.2290	0.1064	0.1572	0.036*
C8	0.22908 (10)	0.11654 (18)	0.05292 (13)	0.0257 (6)
C9	0.17391 (11)	0.11570 (19)	0.03044 (14)	0.0283 (6)
C10	0.15566 (11)	0.1245 (2)	−0.03807 (15)	0.0327 (6)
H10	0.1194	0.1229	−0.0514	0.039*
C11	0.19101 (12)	0.1357 (2)	−0.08821 (14)	0.0346 (7)
H11	0.1782	0.1434	−0.1343	0.041*
C12	0.24389 (12)	0.1353 (2)	−0.06921 (14)	0.0313 (6)
H12	0.2672	0.1423	−0.1026	0.038*
C13	0.26416 (11)	0.12442 (18)	0.00081 (13)	0.0259 (6)
C14	0.31959 (11)	0.12040 (19)	0.01983 (14)	0.0282 (6)
H14	0.3428	0.1249	−0.0139	0.034*
C15	0.69979 (11)	0.1145 (2)	0.07491 (15)	0.0320 (6)
C16	0.75465 (11)	0.11461 (19)	0.10035 (14)	0.0291 (6)
C17	0.77429 (12)	0.1080 (2)	0.17140 (15)	0.0368 (7)
H17	0.7505	0.1042	0.2045	0.044*
C18	0.82731 (12)	0.1072 (2)	0.19168 (15)	0.0369 (7)
H18	0.8394	0.1025	0.2382	0.044*
C19	0.86393 (11)	0.11334 (19)	0.14211 (15)	0.0308 (6)
C20	0.84679 (11)	0.1203 (2)	0.07415 (15)	0.0313 (6)
H20	0.8713	0.1244	0.0420	0.038*
C21	0.79189 (11)	0.12129 (19)	0.05140 (14)	0.0292 (6)
C22	0.77395 (13)	0.1294 (2)	−0.01977 (14)	0.0359 (7)
H22	0.7986	0.1333	−0.0518	0.043*
C23	0.72171 (13)	0.1316 (2)	−0.04176 (15)	0.0386 (7)
H23	0.7106	0.1389	−0.0884	0.046*
C24	0.68428 (12)	0.1228 (2)	0.00593 (15)	0.0364 (7)
H24	0.6484	0.1225	−0.0096	0.044*
H13A	0.475 (3)	−0.008 (6)	0.237 (3)	0.044*	0.50
H13B	0.522 (3)	−0.020 (6)	0.278 (3)	0.044*	0.50
H14A	0.2638 (6)	−0.126 (2)	0.2413 (14)	0.044*
H14B	0.3032 (10)	−0.0816 (19)	0.2865 (13)	0.044*
H17B	0.5565 (11)	0.246 (3)	0.2659 (10)	0.044*
H16A	0.1896 (12)	−0.1887 (13)	0.2014 (17)	0.044*
H16B	0.1879 (12)	−0.0871 (15)	0.1830 (15)	0.044*
H15A	0.3911 (10)	−0.1886 (16)	0.1937 (16)	0.044*
H15B	0.3834 (11)	−0.0917 (16)	0.1692 (16)	0.044*
H14C	0.3202 (8)	−0.135 (2)	0.2350 (13)	0.044*
H17A	0.5954 (8)	0.249 (3)	0.2191 (15)	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0221 (4)	0.0543 (5)	0.0376 (4)	−0.0030 (3)	0.0007 (3)	0.0078 (3)
S2	0.0224 (4)	0.0378 (4)	0.0426 (4)	0.0047 (3)	0.0051 (3)	0.0068 (3)
S3	0.0246 (4)	0.0511 (5)	0.0448 (4)	0.0052 (3)	−0.0020 (3)	0.0043 (4)
S4	0.0234 (4)	0.0358 (4)	0.0523 (5)	0.0032 (3)	−0.0011 (3)	0.0039 (3)
O1	0.0478 (15)	0.0575 (17)	0.123 (3)	−0.0220 (13)	−0.0282 (16)	0.0174 (16)
O2	0.0337 (13)	0.0735 (18)	0.0844 (18)	−0.0031 (12)	−0.0071 (12)	0.0384 (15)
O3	0.0323 (14)	0.205 (4)	0.0516 (16)	0.0188 (18)	0.0080 (12)	−0.017 (2)
O4	0.0449 (13)	0.0592 (15)	0.0690 (16)	0.0028 (11)	0.0223 (12)	−0.0162 (13)
O5	0.0314 (11)	0.0570 (14)	0.0571 (14)	0.0066 (10)	0.0084 (10)	0.0245 (11)
O6	0.0238 (11)	0.0606 (15)	0.0595 (14)	0.0024 (10)	0.0001 (10)	0.0147 (11)
O7	0.0292 (12)	0.0734 (17)	0.0644 (16)	0.0064 (11)	−0.0077 (11)	0.0052 (13)
O8	0.0518 (16)	0.095 (2)	0.112 (2)	0.0260 (15)	0.0260 (16)	0.0648 (19)
O9	0.0512 (16)	0.123 (3)	0.0737 (18)	−0.0174 (16)	0.0215 (14)	−0.0441 (18)
O10	0.0334 (12)	0.0578 (15)	0.0913 (19)	0.0027 (11)	−0.0165 (12)	−0.0259 (14)
O11	0.0336 (12)	0.0631 (16)	0.0747 (17)	0.0088 (11)	−0.0032 (11)	0.0264 (13)
O12	0.0336 (12)	0.0657 (16)	0.0720 (17)	0.0039 (11)	0.0147 (12)	0.0106 (13)
O13	0.054 (2)	0.048 (2)	0.048 (2)	0.000	−0.0149 (16)	0.000
O14	0.0556 (17)	0.0717 (19)	0.0660 (18)	−0.0059 (14)	−0.0087 (14)	−0.0163 (15)
O15	0.0593 (18)	0.0496 (16)	0.107 (2)	−0.0012 (13)	0.0092 (17)	0.0015 (16)
O16	0.0582 (18)	0.0551 (17)	0.114 (3)	−0.0012 (14)	−0.0307 (17)	0.0123 (18)
O17	0.165 (4)	0.119 (3)	0.079 (2)	0.082 (3)	0.048 (3)	0.045 (2)
N1	0.0357 (14)	0.0361 (13)	0.0406 (14)	−0.0019 (11)	0.0035 (11)	−0.0026 (11)
N2	0.0291 (12)	0.0324 (13)	0.0383 (13)	0.0025 (10)	−0.0023 (10)	0.0017 (10)
N3	0.0372 (14)	0.0509 (16)	0.0370 (14)	0.0069 (12)	0.0007 (11)	−0.0005 (12)
C1	0.0299 (15)	0.0381 (16)	0.0433 (17)	0.0007 (12)	−0.0021 (13)	−0.0009 (13)
C2	0.0305 (15)	0.0468 (18)	0.0380 (16)	0.0011 (13)	−0.0013 (12)	−0.0032 (14)
C3	0.0402 (17)	0.0376 (17)	0.0402 (16)	0.0096 (13)	−0.0028 (13)	0.0004 (13)
C4	0.051 (2)	0.0376 (17)	0.0404 (17)	0.0030 (14)	−0.0027 (15)	−0.0010 (13)
C5	0.0259 (14)	0.0270 (14)	0.0334 (15)	−0.0017 (11)	0.0003 (11)	0.0003 (11)
C6	0.0281 (14)	0.0357 (15)	0.0265 (13)	−0.0010 (11)	0.0009 (11)	0.0023 (11)
C7	0.0295 (15)	0.0342 (15)	0.0272 (14)	−0.0011 (11)	0.0058 (11)	0.0027 (11)
C8	0.0267 (14)	0.0204 (12)	0.0302 (14)	0.0015 (10)	0.0031 (11)	0.0008 (10)
C9	0.0256 (14)	0.0237 (13)	0.0358 (15)	0.0024 (10)	0.0033 (11)	0.0027 (11)
C10	0.0269 (14)	0.0296 (14)	0.0400 (16)	0.0039 (11)	−0.0044 (12)	0.0022 (12)
C11	0.0426 (17)	0.0320 (15)	0.0274 (14)	0.0044 (13)	−0.0049 (12)	0.0009 (11)
C12	0.0383 (16)	0.0284 (14)	0.0276 (14)	0.0003 (12)	0.0057 (12)	−0.0002 (11)
C13	0.0298 (14)	0.0190 (12)	0.0291 (13)	0.0013 (10)	0.0036 (11)	−0.0007 (10)
C14	0.0262 (14)	0.0277 (14)	0.0317 (14)	−0.0017 (11)	0.0082 (11)	0.0011 (11)
C15	0.0301 (15)	0.0270 (14)	0.0373 (15)	0.0044 (11)	−0.0031 (12)	0.0006 (12)
C16	0.0304 (14)	0.0246 (13)	0.0314 (14)	0.0038 (11)	−0.0017 (11)	0.0012 (11)
C17	0.0301 (15)	0.0487 (18)	0.0314 (15)	0.0010 (13)	0.0024 (12)	0.0018 (13)
C18	0.0315 (15)	0.0484 (18)	0.0296 (15)	0.0011 (13)	−0.0025 (12)	0.0016 (13)
C19	0.0248 (14)	0.0257 (13)	0.0410 (16)	0.0016 (11)	−0.0006 (12)	−0.0001 (11)
C20	0.0322 (15)	0.0271 (14)	0.0350 (15)	0.0004 (11)	0.0054 (12)	0.0008 (11)
C21	0.0360 (15)	0.0199 (13)	0.0310 (14)	0.0024 (11)	0.0004 (12)	0.0003 (10)
C22	0.0513 (19)	0.0263 (14)	0.0297 (15)	0.0010 (13)	0.0023 (13)	−0.0010 (11)
C23	0.055 (2)	0.0303 (15)	0.0282 (15)	0.0044 (13)	−0.0091 (14)	0.0008 (12)
C24	0.0380 (17)	0.0287 (15)	0.0390 (16)	0.0039 (12)	−0.0120 (13)	−0.0012 (12)

Geometric parameters (Å, º)

S1—O3	1.422 (3)	C2—H2C	0.9700
S1—O2	1.431 (2)	C2—H2D	0.9700
S1—O1	1.445 (3)	C3—C4	1.505 (4)
S1—C5	1.768 (3)	C3—H3D	0.9700
S2—O4	1.448 (2)	C3—H3E	0.9700
S2—O6	1.453 (2)	C4—H4A	0.9700
S2—O5	1.456 (2)	C4—H4B	0.9700
S2—C9	1.776 (3)	C5—C14	1.363 (4)
S3—O7	1.425 (2)	C5—C6	1.414 (4)
S3—O9	1.438 (3)	C6—C7	1.361 (4)
S3—O8	1.453 (3)	C6—H6	0.9300
S3—C15	1.776 (3)	C7—C8	1.418 (4)
S4—O11	1.433 (2)	C7—H7	0.9300
S4—O12	1.446 (3)	C8—C9	1.424 (4)
S4—O10	1.457 (2)	C8—C13	1.424 (4)
S4—C19	1.770 (3)	C9—C10	1.373 (4)
O13—H13A	0.851 (19)	C10—C11	1.403 (4)
O13—H13B	0.85 (2)	C10—H10	0.9300
O14—H14A	0.846 (15)	C11—C12	1.355 (4)
O14—H14B	0.842 (15)	C11—H11	0.9300
O14—H14C	0.850 (15)	C12—C13	1.416 (4)
O15—H15A	0.850 (17)	C12—H12	0.9300
O15—H15B	0.852 (17)	C13—C14	1.418 (4)
O16—H16A	0.800 (16)	C14—H14	0.9300
O16—H16B	0.817 (16)	C15—C24	1.367 (4)
O17—H17B	0.795 (17)	C15—C16	1.429 (4)
O17—H17A	0.888 (16)	C16—C21	1.415 (4)
N1—C1	1.474 (4)	C16—C17	1.426 (4)
N1—H1A	0.8900	C17—C18	1.363 (4)
N1—H1B	0.8900	C17—H17	0.9300
N1—H1C	0.8900	C18—C19	1.413 (4)
N2—C2	1.483 (4)	C18—H18	0.9300
N2—C3	1.493 (4)	C19—C20	1.355 (4)
N2—H2A	0.9000	C20—C21	1.418 (4)
N2—H2B	0.9000	C20—H20	0.9300
N3—C4	1.491 (4)	C21—C22	1.420 (4)
N3—H3A	0.8900	C22—C23	1.351 (4)
N3—H3B	0.8900	C22—H22	0.9300
N3—H3C	0.8900	C23—C24	1.403 (4)
C1—C2	1.511 (4)	C23—H23	0.9300
C1—H1D	0.9700	C24—H24	0.9300
C1—H1E	0.9700
O3—S1—O2	114.2 (2)	N3—C4—C3	113.8 (3)
O3—S1—O1	110.8 (2)	N3—C4—H4A	108.8
O2—S1—O1	110.76 (18)	C3—C4—H4A	108.8
O3—S1—C5	107.56 (14)	N3—C4—H4B	108.8
O2—S1—C5	106.36 (13)	C3—C4—H4B	108.8
O1—S1—C5	106.75 (14)	H4A—C4—H4B	107.7
O4—S2—O6	112.63 (14)	C14—C5—C6	120.9 (2)
O4—S2—O5	112.68 (15)	C14—C5—S1	119.5 (2)
O6—S2—O5	110.26 (13)	C6—C5—S1	119.5 (2)
O4—S2—C9	106.60 (13)	C7—C6—C5	119.6 (2)
O6—S2—C9	106.99 (13)	C7—C6—H6	120.2
O5—S2—C9	107.30 (12)	C5—C6—H6	120.2
O7—S3—O9	114.01 (17)	C6—C7—C8	121.7 (2)
O7—S3—O8	110.52 (17)	C6—C7—H7	119.2
O9—S3—O8	111.8 (2)	C8—C7—H7	119.2
O7—S3—C15	107.96 (14)	C7—C8—C9	125.1 (2)
O9—S3—C15	107.00 (15)	C7—C8—C13	118.1 (2)
O8—S3—C15	105.06 (14)	C9—C8—C13	116.7 (2)
O11—S4—O12	112.14 (15)	C10—C9—C8	121.3 (2)
O11—S4—O10	114.18 (16)	C10—C9—S2	117.6 (2)
O12—S4—O10	110.38 (16)	C8—C9—S2	121.1 (2)
O11—S4—C19	107.10 (13)	C9—C10—C11	120.8 (3)
O12—S4—C19	107.45 (14)	C9—C10—H10	119.6
O10—S4—C19	105.07 (13)	C11—C10—H10	119.6
H13A—O13—H13B	109 (3)	C12—C11—C10	119.8 (3)
H14A—O14—H14B	110.9 (19)	C12—C11—H11	120.1
H14A—O14—H14C	118 (2)	C10—C11—H11	120.1
H14B—O14—H14C	104.1 (18)	C11—C12—C13	120.9 (3)
H15A—O15—H15B	107 (2)	C11—C12—H12	119.5
H16A—O16—H16B	118 (2)	C13—C12—H12	119.5
H17B—O17—H17A	114 (2)	C12—C13—C14	120.4 (2)
C1—N1—H1A	109.5	C12—C13—C8	120.3 (2)
C1—N1—H1B	109.5	C14—C13—C8	119.2 (2)
H1A—N1—H1B	109.5	C5—C14—C13	120.4 (2)
C1—N1—H1C	109.5	C5—C14—H14	119.8
H1A—N1—H1C	109.5	C13—C14—H14	119.8
H1B—N1—H1C	109.5	C24—C15—C16	120.8 (3)
C2—N2—C3	114.0 (2)	C24—C15—S3	117.6 (2)
C2—N2—H2A	108.8	C16—C15—S3	121.5 (2)
C3—N2—H2A	108.8	C21—C16—C17	118.0 (3)
C2—N2—H2B	108.8	C21—C16—C15	117.5 (2)
C3—N2—H2B	108.8	C17—C16—C15	124.5 (3)
H2A—N2—H2B	107.7	C18—C17—C16	121.1 (3)
C4—N3—H3A	109.5	C18—C17—H17	119.4
C4—N3—H3B	109.5	C16—C17—H17	119.4
H3A—N3—H3B	109.5	C17—C18—C19	120.1 (3)
C4—N3—H3C	109.5	C17—C18—H18	119.9
H3A—N3—H3C	109.5	C19—C18—H18	119.9
H3B—N3—H3C	109.5	C20—C19—C18	120.5 (3)
N1—C1—C2	111.1 (2)	C20—C19—S4	121.1 (2)
N1—C1—H1D	109.4	C18—C19—S4	118.4 (2)
C2—C1—H1D	109.4	C19—C20—C21	120.8 (3)
N1—C1—H1E	109.4	C19—C20—H20	119.6
C2—C1—H1E	109.4	C21—C20—H20	119.6
H1D—C1—H1E	108.0	C16—C21—C20	119.5 (2)
N2—C2—C1	110.0 (2)	C16—C21—C22	119.8 (3)
N2—C2—H2C	109.7	C20—C21—C22	120.7 (3)
C1—C2—H2C	109.7	C23—C22—C21	121.1 (3)
N2—C2—H2D	109.7	C23—C22—H22	119.5
C1—C2—H2D	109.7	C21—C22—H22	119.5
H2C—C2—H2D	108.2	C22—C23—C24	119.9 (3)
N2—C3—C4	113.6 (3)	C22—C23—H23	120.1
N2—C3—H3D	108.9	C24—C23—H23	120.1
C4—C3—H3D	108.9	C15—C24—C23	121.0 (3)
N2—C3—H3E	108.9	C15—C24—H24	119.5
C4—C3—H3E	108.9	C23—C24—H24	119.5
H3D—C3—H3E	107.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O17	0.89	1.83	2.706 (5)	170
N1—H1B···O11^i	0.89	2.39	2.923 (3)	119
N1—H1B···O11^ii	0.89	2.21	3.025 (4)	152
N1—H1C···O5^iii	0.89	2.07	2.946 (3)	166
N1—H1C···O6^iii	0.89	2.57	3.240 (3)	132
N2—H2A···O6^iv	0.90	1.94	2.774 (4)	154
N2—H2B···O1	0.90	2.42	3.222 (4)	149
N2—H2B···O3	0.90	2.22	2.988 (4)	143
N3—H3A···O4^iv	0.89	1.95	2.844 (4)	179
N3—H3B···O13^v	0.89	2.19	2.917 (4)	138
N3—H3C···O12^vi	0.89	2.43	3.204 (4)	145
N3—H3C···O10^vi	0.89	2.25	3.071 (4)	154
O13—H13A···O2	0.85	2.00 (2)	2.768 (4)	149
O13—H13B···O2^vii	0.85 (6)	1.93 (1)	2.768 (3)	170
O14—H14A···O16	0.85 (2)	1.64 (2)	2.476 (4)	172 (3)
O14—H14B···O8^vii	0.84 (3)	1.70 (3)	2.503 (4)	158
O14—H14C···O15	0.85 (2)	1.62 (2)	2.473 (4)	180
O15—H15A···O10^viii	0.85 (2)	1.84 (3)	2.687 (4)	180
O15—H15B···O2	0.85 (2)	1.90 (3)	2.704 (4)	158 (3)
O16—H16A···O9^viii	0.80 (2)	2.02 (2)	2.813 (5)	175
O16—H16B···O5	0.82 (2)	2.01 (3)	2.820 (4)	170 (3)
O17—H17A···O9	0.89 (3)	2.05 (3)	2.856 (5)	150 (3)
O17—H17B···O1^vii	0.80 (2)	2.08 (2)	2.821 (5)	156
C1—H1E···O1	0.97	2.35	3.206 (4)	146
C2—H2D···O7	0.97	2.44	3.247 (4)	140
C3—H3D···O7	0.97	2.42	3.227 (4)	141
C3—H3E···O12^vi	0.97	2.52	3.158 (4)	123
C4—H4B···O3	0.97	2.44	3.167 (4)	131
C7—H7···O5	0.93	2.60	3.139 (3)	118
C10—H10···O6	0.93	2.42	2.847 (4)	108
C14—H14···O3	0.93	2.55	2.912 (4)	104
C17—H17···O9	0.93	2.52	3.120 (4)	122
C20—H20···O12	0.93	2.52	2.913 (4)	106
C24—H24···O7	0.93	2.43	2.854 (4)	108

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