Bis­[trimethyl(tetra­decyl)ammonium] 7-hydroxy-8-phenyl­diazenyl-7,8-di­hydro­naph­tha­lene-1,3-di­sulfonate 1.8-hydrate: ionic self-assembly

Ionic self-assembly of the azobenzene dye Orange G with the surfactant tetradecylammonium bromide leads to the title compound, 2C₁₇H₃₈N⁺·C₁₆H₁₀N₂O₇S₂^2-·1.8H₂O, which has an unusual highly regular nanostructure with ionic layers and with alternating dye and surfactant stacks.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.052
• wR factor = 0.075
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         32 Perc.
PLAT731_ALERT_1_B Bond    Calc     0.91(5), Rep   0.899(10) ......       5.00 su-Rat
              O2   -H21     1.555   1.555

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.745
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.106
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         S2
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      40.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N4     -   H4     ...       1.01 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.89(3), Rep   0.895(10) ......       3.00 su-Rat
              O2   -H22     1.555   1.555
PLAT732_ALERT_1_C Angle   Calc      109(5), Rep   109.4(16) ......       3.12 su-Rat
              H22  -O2   -H21     1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA WinExpose (Stoe & Cie, 2002); cell refinement: X-AREA WinCell (Stoe & Cie, 2002); data reduction: X-AREA WinIntegrate (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: DIAMOND2 (Crystal Impact, 2000).

Bis(tetradecylammonium) 7-hydroxy-8-phenyldiazenyl-7,8-dihydronaphthalene-1,3-disulfonate 1.8-hydrate

Crystal data

2C17H38N^+·C16H10N2O7S2^2^−·1.8H2O	Z = 2
Mr = 951.78	F(000) = 1040
Triclinic, P1	Dx = 1.172 Mg m^−3
a = 8.2811 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.071 (2) Å	Cell parameters from 7804 reflections
c = 25.204 (4) Å	θ = 1.6–26.0°
α = 85.82 (1)°	µ = 0.15 mm^−1
β = 87.96 (1)°	T = 193 K
γ = 82.54 (1)°	Needle, orange
V = 2696.9 (7) Å^3	0.50 × 0.04 × 0.02 mm

Data collection

Stoe IPDS-II diffractometer	10547 independent reflections
Radiation source: fine-focus sealed tube	3416 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.106
Detector resolution: 150 pixels mm^-1	θmax = 26.2°, θmin = 1.6°
ω scans	h = −9→10
Absorption correction: multi-scan (XPREP in SHELXTL; Siemens, 1996)	k = −16→15
Tmin = 0.889, Tmax = 0.997	l = −31→31
23823 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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2)]
S = 0.75	(Δ/σ)max < 0.001
10547 reflections	Δρmax = 0.23 e Å^−3
605 parameters	Δρmin = −0.35 e Å^−3
7 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00054 (2)

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	0.79371 (13)	0.01103 (7)	0.37384 (4)	0.0352 (3)
S2	0.64743 (14)	0.41895 (8)	0.40115 (4)	0.0419 (3)
N1	0.1583 (4)	−0.3599 (2)	0.39579 (13)	0.0403 (9)
N2	0.2511 (4)	0.0949 (2)	0.43491 (12)	0.0361 (8)
N3	0.8634 (4)	−0.0048 (2)	0.25755 (12)	0.0345 (8)
N4	0.9225 (4)	−0.0704 (2)	0.22325 (13)	0.0399 (8)
H4	0.973 (4)	−0.052 (3)	0.1875 (7)	0.048*
O1	0.5603 (5)	−0.2106 (3)	0.4131 (2)	0.080 (2)	0.803 (8)
H11	0.607 (8)	−0.152 (3)	0.409 (3)	0.19 (3)*	0.803 (8)
H12	0.641 (6)	−0.264 (4)	0.416 (4)	0.19 (3)*	0.803 (8)
O2	0.2847 (4)	0.3749 (2)	0.51462 (12)	0.0573 (8)
H22	0.275 (8)	0.435 (2)	0.530 (2)	0.19 (2)*
H21	0.370 (5)	0.372 (4)	0.491 (2)	0.19 (2)*
O3	1.0299 (4)	0.0663 (2)	0.16385 (11)	0.0545 (8)
O11	0.9524 (3)	−0.04288 (17)	0.35998 (9)	0.0371 (6)
O12	0.6540 (3)	−0.03404 (19)	0.35607 (10)	0.0408 (7)
O13	0.7782 (3)	0.02884 (17)	0.43101 (9)	0.0429 (7)
O21	0.5925 (4)	0.5095 (2)	0.36670 (11)	0.0694 (10)
O22	0.7824 (3)	0.4334 (2)	0.43364 (11)	0.0565 (8)
O23	0.5177 (3)	0.3756 (2)	0.43269 (12)	0.0697 (10)
C1	0.7866 (4)	0.1390 (3)	0.34114 (14)	0.0280 (9)
C2	0.7284 (4)	0.2172 (3)	0.37394 (15)	0.0337 (10)
H2A	0.6897	0.1984	0.4088	0.040*
C3	0.7240 (4)	0.3226 (3)	0.35809 (15)	0.0345 (9)
C4	0.7841 (5)	0.3491 (3)	0.30792 (15)	0.0410 (11)
H4B	0.7844	0.4200	0.2965	0.049*
C5	0.8447 (5)	0.2729 (3)	0.27358 (15)	0.0367 (10)
C6	0.8399 (5)	0.1651 (3)	0.28763 (15)	0.0332 (10)
C7	0.9084 (5)	0.3049 (3)	0.22187 (15)	0.0469 (12)
H7A	0.9042	0.3768	0.2121	0.056*
C8	0.9734 (5)	0.2373 (3)	0.18708 (17)	0.0490 (12)
H8A	1.0222	0.2615	0.1547	0.059*
C9	0.9696 (5)	0.1291 (3)	0.19837 (15)	0.0422 (11)
C10	0.8970 (5)	0.0936 (3)	0.24786 (14)	0.0324 (9)
C11	0.8895 (5)	−0.1746 (3)	0.22977 (15)	0.0364 (10)
C11N	0.2760 (5)	−0.3451 (3)	0.43644 (15)	0.0534 (12)
H11B	0.2301	−0.3615	0.4720	0.080*
H11C	0.2982	−0.2730	0.4335	0.080*
H11D	0.3776	−0.3910	0.4308	0.080*
C12	0.9559 (5)	−0.2383 (3)	0.19115 (17)	0.0490 (12)
H12B	1.0173	−0.2119	0.1619	0.059*
C12N	0.0008 (5)	−0.2957 (3)	0.40639 (16)	0.0546 (12)
H12C	−0.0390	−0.3137	0.4425	0.082*
H12D	−0.0790	−0.3085	0.3806	0.082*
H12E	0.0163	−0.2224	0.4030	0.082*
C13	0.9313 (6)	−0.3413 (3)	0.19595 (18)	0.0586 (13)
H13B	0.9758	−0.3867	0.1699	0.070*
C13N	0.1326 (6)	−0.4728 (3)	0.39953 (17)	0.0610 (14)
H13C	0.0889	−0.4917	0.4350	0.092*
H13D	0.2369	−0.5156	0.3933	0.092*
H13E	0.0555	−0.4843	0.3726	0.092*
C14	0.8416 (6)	−0.3779 (3)	0.23891 (18)	0.0589 (13)
H14A	0.8248	−0.4487	0.2417	0.071*
C15	0.7761 (5)	−0.3151 (3)	0.27768 (17)	0.0511 (12)
H15A	0.7153	−0.3419	0.3070	0.061*
C16	0.8006 (5)	−0.2105 (3)	0.27323 (15)	0.0422 (11)
H16A	0.7571	−0.1652	0.2995	0.051*
C21N	0.3944 (5)	0.1208 (3)	0.46358 (15)	0.0486 (11)
H21B	0.4952	0.0868	0.4477	0.073*
H21C	0.3860	0.0967	0.5012	0.073*
H21D	0.3957	0.1959	0.4606	0.073*
C22N	0.0972 (5)	0.1482 (3)	0.45893 (15)	0.0506 (12)
H22B	0.0924	0.1289	0.4972	0.076*
H22C	0.0030	0.1273	0.4421	0.076*
H22D	0.0958	0.2233	0.4532	0.076*
C23N	0.2480 (5)	−0.0204 (3)	0.44129 (15)	0.0487 (11)
H23B	0.3478	−0.0557	0.4254	0.073*
H23C	0.1532	−0.0381	0.4234	0.073*
H23D	0.2412	−0.0425	0.4792	0.073*
C101	0.2258 (5)	−0.3346 (3)	0.33972 (15)	0.0432 (11)
H10A	0.3299	−0.3796	0.3343	0.052*
H10B	0.1484	−0.3510	0.3135	0.052*
C102	0.2552 (5)	−0.2217 (3)	0.32877 (15)	0.0428 (11)
H10C	0.1510	−0.1760	0.3326	0.051*
H10D	0.3310	−0.2040	0.3552	0.051*
C103	0.3270 (5)	−0.2037 (3)	0.27281 (14)	0.0395 (11)
H10E	0.4320	−0.2488	0.2691	0.047*
H10F	0.2519	−0.2223	0.2464	0.047*
C104	0.3542 (5)	−0.0912 (3)	0.26174 (15)	0.0406 (11)
H10G	0.4272	−0.0726	0.2888	0.049*
H10H	0.2487	−0.0466	0.2651	0.049*
C105	0.4295 (5)	−0.0699 (3)	0.20603 (15)	0.0440 (11)
H10I	0.3559	−0.0875	0.1789	0.053*
H10J	0.5344	−0.1151	0.2025	0.053*
C106	0.4590 (5)	0.0441 (3)	0.19529 (16)	0.0476 (12)
H10K	0.3528	0.0886	0.1947	0.057*
H10L	0.5219	0.0640	0.2247	0.057*
C107	0.5520 (5)	0.0631 (3)	0.14232 (16)	0.0485 (12)
H10M	0.6642	0.0267	0.1451	0.058*
H10N	0.4982	0.0330	0.1138	0.058*
C108	0.5602 (5)	0.1771 (3)	0.12687 (15)	0.0461 (11)
H10O	0.6090	0.2081	0.1562	0.055*
H10P	0.4483	0.2129	0.1222	0.055*
C109	0.6614 (5)	0.1945 (3)	0.07512 (16)	0.0483 (12)
H10Q	0.7745	0.1611	0.0804	0.058*
H10R	0.6154	0.1607	0.0462	0.058*
C110	0.6642 (5)	0.3094 (3)	0.05807 (16)	0.0495 (12)
H11E	0.5511	0.3434	0.0535	0.059*
H11F	0.7129	0.3431	0.0865	0.059*
C111	0.7619 (5)	0.3245 (3)	0.00600 (16)	0.0484 (12)
H11G	0.8752	0.2912	0.0111	0.058*
H11H	0.7146	0.2889	−0.0219	0.058*
C112	0.7654 (5)	0.4377 (3)	−0.01336 (16)	0.0470 (12)
H11I	0.6528	0.4708	−0.0200	0.056*
H11J	0.8098	0.4743	0.0148	0.056*
C113	0.8692 (5)	0.4487 (3)	−0.06427 (17)	0.0556 (13)
H11K	0.8241	0.4124	−0.0923	0.067*
H11L	0.9812	0.4147	−0.0576	0.067*
C114	0.8765 (6)	0.5626 (3)	−0.08460 (18)	0.0622 (14)
H11M	0.9448	0.5649	−0.1171	0.093*
H11N	0.9232	0.5989	−0.0573	0.093*
H11O	0.7663	0.5964	−0.0923	0.093*
C201	0.2631 (5)	0.1237 (3)	0.37516 (14)	0.0435 (11)
H20A	0.3679	0.0894	0.3611	0.052*
H20B	0.1746	0.0959	0.3576	0.052*
C202	0.2524 (5)	0.2384 (3)	0.35979 (16)	0.0457 (11)
H20C	0.3217	0.2711	0.3831	0.055*
H20D	0.1385	0.2713	0.3642	0.055*
C203	0.3100 (5)	0.2538 (3)	0.30148 (15)	0.0469 (12)
H20E	0.2381	0.2230	0.2783	0.056*
H20F	0.4220	0.2180	0.2970	0.056*
C204	0.3077 (5)	0.3697 (3)	0.28458 (15)	0.0474 (12)
H20G	0.1935	0.4034	0.2843	0.057*
H20H	0.3663	0.4025	0.3110	0.057*
C205	0.3870 (5)	0.3870 (3)	0.22937 (16)	0.0493 (12)
H20I	0.3222	0.3601	0.2025	0.059*
H20J	0.4976	0.3477	0.2287	0.059*
C206	0.3994 (5)	0.5028 (3)	0.21447 (16)	0.0491 (12)
H20K	0.2883	0.5405	0.2109	0.059*
H20L	0.4522	0.5317	0.2436	0.059*
C207	0.4972 (5)	0.5204 (3)	0.16223 (15)	0.0487 (12)
H20M	0.6098	0.4854	0.1664	0.058*
H20N	0.4475	0.4884	0.1335	0.058*
C208	0.5031 (5)	0.6345 (3)	0.14599 (16)	0.0515 (12)
H20O	0.5475	0.6675	0.1755	0.062*
H20P	0.3909	0.6689	0.1399	0.062*
C209	0.6076 (5)	0.6508 (3)	0.09574 (16)	0.0496 (12)
H20Q	0.5607	0.6201	0.0659	0.059*
H20R	0.7186	0.6141	0.1014	0.059*
C210	0.6192 (5)	0.7659 (3)	0.08038 (16)	0.0529 (12)
H21E	0.5077	0.8028	0.0762	0.063*
H21F	0.6695	0.7956	0.1098	0.063*
C211	0.7183 (5)	0.7845 (3)	0.02898 (17)	0.0544 (13)
H21G	0.8307	0.7493	0.0334	0.065*
H21H	0.6698	0.7532	−0.0003	0.065*
C212	0.7247 (5)	0.8990 (3)	0.01348 (16)	0.0513 (12)
H21I	0.7763	0.9298	0.0423	0.062*
H21J	0.6121	0.9346	0.0101	0.062*
C213	0.8194 (6)	0.9179 (3)	−0.03879 (17)	0.0550 (13)
H21K	0.7684	0.8872	−0.0677	0.066*
H21L	0.9325	0.8832	−0.0355	0.066*
C214	0.8224 (6)	1.0338 (3)	−0.05334 (17)	0.0597 (13)
H21M	0.8843	1.0430	−0.0868	0.090*
H21N	0.8742	1.0643	−0.0250	0.090*
H21O	0.7106	1.0681	−0.0574	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0418 (7)	0.0271 (5)	0.0354 (6)	−0.0022 (5)	0.0003 (5)	0.0020 (4)
S2	0.0449 (7)	0.0308 (6)	0.0490 (7)	0.0002 (5)	0.0078 (6)	−0.0087 (5)
N1	0.041 (2)	0.035 (2)	0.042 (2)	0.0003 (17)	0.0092 (18)	0.0042 (16)
N2	0.035 (2)	0.0382 (19)	0.0352 (19)	−0.0051 (16)	0.0009 (15)	−0.0013 (15)
N3	0.033 (2)	0.0330 (19)	0.0372 (19)	0.0005 (15)	−0.0010 (15)	−0.0053 (15)
N4	0.049 (2)	0.0306 (19)	0.040 (2)	−0.0042 (16)	0.0057 (17)	−0.0037 (16)
O1	0.062 (3)	0.060 (3)	0.118 (4)	−0.026 (2)	−0.019 (3)	0.033 (3)
O2	0.066 (2)	0.0470 (19)	0.062 (2)	−0.0179 (16)	0.0163 (17)	−0.0116 (16)
O3	0.070 (2)	0.0442 (18)	0.0490 (19)	−0.0088 (16)	0.0181 (16)	−0.0077 (15)
O11	0.0342 (16)	0.0279 (13)	0.0452 (16)	0.0075 (12)	−0.0005 (12)	0.0031 (12)
O12	0.0386 (17)	0.0358 (15)	0.0497 (17)	−0.0106 (13)	−0.0050 (13)	−0.0025 (13)
O13	0.068 (2)	0.0336 (15)	0.0260 (15)	−0.0047 (13)	0.0046 (13)	0.0024 (11)
O21	0.103 (3)	0.0358 (17)	0.060 (2)	0.0274 (17)	−0.0051 (19)	−0.0033 (15)
O22	0.0496 (19)	0.061 (2)	0.062 (2)	−0.0066 (16)	−0.0070 (16)	−0.0232 (15)
O23	0.058 (2)	0.069 (2)	0.087 (2)	−0.0283 (18)	0.0502 (18)	−0.0321 (18)
C1	0.030 (2)	0.023 (2)	0.031 (2)	−0.0037 (17)	−0.0006 (18)	0.0004 (16)
C2	0.029 (2)	0.030 (2)	0.041 (2)	−0.0026 (17)	0.0016 (19)	0.0018 (19)
C3	0.031 (2)	0.030 (2)	0.041 (2)	0.0019 (18)	0.0081 (19)	−0.0084 (17)
C4	0.044 (3)	0.029 (2)	0.047 (3)	0.0028 (19)	0.009 (2)	0.0020 (19)
C5	0.042 (3)	0.026 (2)	0.040 (2)	0.0008 (19)	0.006 (2)	0.0006 (18)
C6	0.035 (2)	0.026 (2)	0.039 (2)	−0.0002 (18)	0.0056 (19)	−0.0056 (17)
C7	0.070 (3)	0.030 (2)	0.039 (3)	−0.007 (2)	0.015 (2)	0.002 (2)
C8	0.065 (3)	0.036 (3)	0.044 (3)	−0.007 (2)	0.015 (2)	0.003 (2)
C9	0.054 (3)	0.036 (2)	0.036 (2)	−0.002 (2)	0.006 (2)	−0.008 (2)
C10	0.038 (2)	0.021 (2)	0.037 (2)	0.0015 (18)	0.0038 (19)	−0.0068 (17)
C11	0.038 (3)	0.025 (2)	0.046 (3)	−0.0014 (19)	−0.003 (2)	−0.0052 (19)
C11N	0.060 (3)	0.050 (3)	0.048 (3)	0.001 (2)	−0.003 (2)	0.002 (2)
C12	0.054 (3)	0.039 (3)	0.054 (3)	−0.005 (2)	−0.003 (2)	−0.007 (2)
C12N	0.045 (3)	0.056 (3)	0.056 (3)	0.008 (2)	0.017 (2)	0.003 (2)
C13	0.074 (4)	0.038 (3)	0.064 (3)	0.000 (2)	0.001 (3)	−0.018 (2)
C13N	0.081 (4)	0.035 (3)	0.066 (3)	−0.012 (2)	0.017 (3)	0.002 (2)
C14	0.083 (4)	0.030 (3)	0.065 (3)	−0.012 (2)	−0.007 (3)	−0.002 (2)
C15	0.067 (3)	0.032 (3)	0.054 (3)	−0.009 (2)	0.004 (2)	0.004 (2)
C16	0.034 (2)	0.049 (3)	0.043 (3)	−0.003 (2)	−0.004 (2)	−0.003 (2)
C21N	0.047 (3)	0.049 (3)	0.053 (3)	−0.013 (2)	−0.013 (2)	0.001 (2)
C22N	0.039 (3)	0.062 (3)	0.049 (3)	0.002 (2)	0.008 (2)	−0.005 (2)
C23N	0.063 (3)	0.038 (2)	0.045 (3)	−0.008 (2)	−0.004 (2)	0.003 (2)
C101	0.042 (3)	0.048 (3)	0.037 (2)	0.001 (2)	0.011 (2)	0.000 (2)
C102	0.051 (3)	0.034 (2)	0.042 (3)	−0.004 (2)	0.006 (2)	0.0010 (19)
C103	0.042 (3)	0.039 (2)	0.037 (2)	−0.005 (2)	0.005 (2)	0.0052 (19)
C104	0.037 (3)	0.043 (3)	0.041 (3)	−0.005 (2)	0.006 (2)	−0.003 (2)
C105	0.045 (3)	0.042 (3)	0.045 (3)	−0.006 (2)	0.003 (2)	−0.003 (2)
C106	0.048 (3)	0.046 (3)	0.048 (3)	−0.008 (2)	0.005 (2)	−0.003 (2)
C107	0.056 (3)	0.047 (3)	0.042 (3)	−0.009 (2)	−0.001 (2)	0.003 (2)
C108	0.051 (3)	0.042 (3)	0.046 (3)	−0.011 (2)	0.007 (2)	−0.006 (2)
C109	0.058 (3)	0.043 (3)	0.043 (3)	−0.011 (2)	0.007 (2)	0.003 (2)
C110	0.054 (3)	0.042 (3)	0.052 (3)	−0.009 (2)	0.007 (2)	−0.002 (2)
C111	0.049 (3)	0.042 (3)	0.053 (3)	−0.008 (2)	0.011 (2)	0.004 (2)
C112	0.052 (3)	0.037 (3)	0.052 (3)	−0.007 (2)	−0.001 (2)	0.001 (2)
C113	0.063 (3)	0.044 (3)	0.057 (3)	−0.006 (2)	0.002 (3)	0.011 (2)
C114	0.072 (4)	0.049 (3)	0.064 (3)	−0.011 (3)	0.007 (3)	0.011 (2)
C201	0.052 (3)	0.043 (3)	0.035 (2)	−0.007 (2)	−0.001 (2)	−0.0003 (19)
C202	0.046 (3)	0.042 (3)	0.046 (3)	0.002 (2)	0.004 (2)	0.003 (2)
C203	0.051 (3)	0.046 (3)	0.040 (3)	0.000 (2)	0.000 (2)	0.008 (2)
C204	0.054 (3)	0.052 (3)	0.034 (3)	−0.005 (2)	0.002 (2)	0.000 (2)
C205	0.053 (3)	0.049 (3)	0.045 (3)	−0.003 (2)	0.003 (2)	−0.004 (2)
C206	0.053 (3)	0.044 (3)	0.050 (3)	−0.005 (2)	0.003 (2)	−0.002 (2)
C207	0.053 (3)	0.051 (3)	0.042 (3)	−0.009 (2)	0.002 (2)	0.001 (2)
C208	0.054 (3)	0.047 (3)	0.053 (3)	−0.006 (2)	0.008 (2)	−0.002 (2)
C209	0.053 (3)	0.046 (3)	0.048 (3)	−0.003 (2)	0.002 (2)	−0.001 (2)
C210	0.055 (3)	0.048 (3)	0.053 (3)	−0.001 (2)	0.008 (2)	0.000 (2)
C211	0.054 (3)	0.048 (3)	0.059 (3)	−0.001 (2)	0.003 (2)	0.003 (2)
C212	0.050 (3)	0.049 (3)	0.052 (3)	0.003 (2)	0.009 (2)	−0.002 (2)
C213	0.064 (3)	0.050 (3)	0.050 (3)	−0.004 (2)	0.007 (2)	0.001 (2)
C214	0.075 (4)	0.045 (3)	0.057 (3)	−0.003 (3)	0.002 (3)	0.000 (2)

Geometric parameters (Å, º)

S1—O11	1.452 (2)	C8—C9	1.426 (5)
S1—O12	1.462 (3)	C9—C10	1.438 (5)
S1—O13	1.475 (2)	C11—C12	1.380 (5)
S1—C1	1.805 (3)	C11—C16	1.385 (5)
S2—O21	1.449 (3)	C12—C13	1.384 (5)
S2—O22	1.449 (3)	C13—C14	1.383 (5)
S2—O23	1.463 (3)	C14—C15	1.374 (6)
S2—C3	1.763 (4)	C15—C16	1.404 (5)
N1—C11N	1.479 (5)	C101—C102	1.531 (5)
N1—C12N	1.483 (5)	C102—C103	1.525 (5)
N1—C13N	1.514 (5)	C103—C104	1.522 (5)
N1—C101	1.531 (4)	C104—C105	1.537 (5)
N2—C21N	1.499 (4)	C105—C106	1.544 (5)
N2—C22N	1.501 (5)	C106—C107	1.538 (5)
N2—C23N	1.508 (4)	C107—C108	1.521 (5)
N2—C201	1.529 (4)	C108—C109	1.544 (5)
N3—N4	1.300 (4)	C109—C110	1.535 (5)
N3—C10	1.355 (4)	C110—C111	1.531 (5)
N4—H4	1.007 (10)	C111—C112	1.528 (5)
N4—C11	1.421 (4)	C112—C113	1.527 (5)
O1—H12	0.902 (10)	C113—C114	1.547 (5)
O1—H11	0.905 (10)	C201—C202	1.513 (5)
O2—H22	0.895 (10)	C202—C203	1.536 (5)
O2—H21	0.899 (10)	C203—C204	1.541 (5)
O3—C9	1.283 (4)	C204—C205	1.532 (5)
C1—C2	1.388 (5)	C205—C206	1.548 (5)
C1—C6	1.435 (4)	C206—C207	1.539 (5)
C2—C3	1.403 (5)	C207—C208	1.525 (5)
C3—C4	1.379 (4)	C208—C209	1.526 (5)
C4—C5	1.399 (5)	C209—C210	1.540 (5)
C5—C6	1.433 (5)	C210—C211	1.530 (5)
C5—C7	1.443 (5)	C211—C212	1.527 (5)
C6—C10	1.445 (5)	C212—C213	1.530 (5)
C7—C8	1.340 (5)	C213—C214	1.536 (5)
O11—S1—O12	115.43 (16)	C1—C6—C10	126.7 (3)
O11—S1—O13	111.83 (15)	C8—C7—C5	122.5 (4)
O12—S1—O13	111.36 (15)	C7—C8—C9	120.4 (4)
O11—S1—C1	105.85 (15)	O3—C9—C8	119.0 (4)
O12—S1—C1	107.17 (16)	O3—C9—C10	121.9 (3)
O13—S1—C1	104.31 (16)	C8—C9—C10	119.1 (4)
O21—S2—O22	113.11 (19)	N3—C10—C9	122.4 (3)
O21—S2—O23	114.52 (19)	N3—C10—C6	116.4 (3)
O22—S2—O23	111.84 (18)	C9—C10—C6	120.9 (3)
O21—S2—C3	105.42 (18)	C12—C11—C16	122.3 (4)
O22—S2—C3	105.90 (18)	C12—C11—N4	115.8 (4)
O23—S2—C3	105.08 (18)	C16—C11—N4	121.8 (4)
C11N—N1—C12N	109.5 (3)	C11—C12—C13	118.6 (4)
C11N—N1—C13N	108.3 (3)	C14—C13—C12	119.7 (4)
C12N—N1—C13N	109.2 (3)	C15—C14—C13	122.0 (4)
C11N—N1—C101	110.9 (3)	C14—C15—C16	118.8 (4)
C12N—N1—C101	111.5 (3)	C11—C16—C15	118.6 (4)
C13N—N1—C101	107.3 (3)	C102—C101—N1	114.1 (3)
C21N—N2—C22N	109.3 (3)	C103—C102—C101	110.8 (3)
C21N—N2—C23N	108.8 (3)	C104—C103—C102	110.7 (3)
C22N—N2—C23N	109.1 (3)	C103—C104—C105	112.5 (3)
C21N—N2—C201	112.0 (3)	C104—C105—C106	112.3 (3)
C22N—N2—C201	110.9 (3)	C107—C106—C105	112.5 (3)
C23N—N2—C201	106.7 (3)	C108—C107—C106	113.4 (3)
N4—N3—C10	116.4 (3)	C107—C108—C109	112.7 (3)
H4—N4—N3	125 (2)	C110—C109—C108	112.9 (3)
H4—N4—C11	114 (2)	C111—C110—C109	111.8 (3)
N3—N4—C11	119.9 (3)	C112—C111—C110	113.9 (3)
H12—O1—H11	107.6 (16)	C113—C112—C111	111.9 (3)
H22—O2—H21	109.4 (16)	C112—C113—C114	113.1 (4)
C2—C1—C6	119.7 (3)	C202—C201—N2	115.2 (3)
C2—C1—S1	113.4 (3)	C201—C202—C203	108.9 (3)
C6—C1—S1	126.8 (3)	C202—C203—C204	110.8 (3)
C1—C2—C3	123.1 (3)	C205—C204—C203	111.9 (3)
C4—C3—C2	118.0 (3)	C204—C205—C206	112.1 (3)
C4—C3—S2	120.7 (3)	C207—C206—C205	112.7 (3)
C2—C3—S2	121.3 (3)	C208—C207—C206	113.0 (3)
C3—C4—C5	120.8 (3)	C207—C208—C209	112.4 (3)
C4—C5—C6	122.0 (3)	C208—C209—C210	112.6 (3)
C4—C5—C7	118.5 (3)	C211—C210—C209	113.6 (4)
C6—C5—C7	119.5 (4)	C212—C211—C210	113.0 (4)
C5—C6—C1	116.0 (3)	C211—C212—C213	113.1 (3)
C5—C6—C10	117.2 (3)	C212—C213—C214	111.7 (4)
C10—N3—N4—H4	−12 (2)	C1—C6—C10—C9	−170.6 (4)
C10—N3—N4—C11	−178.4 (3)	H4—N4—C11—C12	11 (2)
O11—S1—C1—C2	−133.7 (3)	N3—N4—C11—C12	179.4 (4)
O12—S1—C1—C2	102.6 (3)	H4—N4—C11—C16	−171 (2)
O13—S1—C1—C2	−15.6 (3)	N3—N4—C11—C16	−2.8 (5)
O11—S1—C1—C6	43.6 (4)	C16—C11—C12—C13	0.6 (7)
O12—S1—C1—C6	−80.1 (4)	N4—C11—C12—C13	178.5 (4)
O13—S1—C1—C6	161.7 (3)	C11—C12—C13—C14	0.0 (7)
C6—C1—C2—C3	−2.4 (6)	C12—C13—C14—C15	−0.4 (7)
S1—C1—C2—C3	175.0 (3)	C13—C14—C15—C16	0.3 (7)
C1—C2—C3—C4	−1.5 (6)	C12—C11—C16—C15	−0.7 (6)
C1—C2—C3—S2	179.5 (3)	N4—C11—C16—C15	−178.5 (4)
O21—S2—C3—C4	26.5 (4)	C14—C15—C16—C11	0.3 (6)
O22—S2—C3—C4	−93.6 (3)	C11N—N1—C101—C102	−63.2 (4)
O23—S2—C3—C4	147.9 (3)	C12N—N1—C101—C102	59.1 (4)
O21—S2—C3—C2	−154.6 (3)	C13N—N1—C101—C102	178.7 (4)
O22—S2—C3—C2	85.3 (3)	N1—C101—C102—C103	178.3 (3)
O23—S2—C3—C2	−33.2 (4)	C101—C102—C103—C104	179.3 (4)
C2—C3—C4—C5	1.2 (6)	C102—C103—C104—C105	179.0 (3)
S2—C3—C4—C5	−179.8 (3)	C103—C104—C105—C106	−179.2 (4)
C3—C4—C5—C6	3.1 (6)	C104—C105—C106—C107	173.5 (4)
C3—C4—C5—C7	−179.0 (4)	C105—C106—C107—C108	171.3 (4)
C4—C5—C6—C1	−6.8 (6)	C106—C107—C108—C109	177.1 (4)
C7—C5—C6—C1	175.4 (4)	C107—C108—C109—C110	177.6 (4)
C4—C5—C6—C10	176.4 (4)	C108—C109—C110—C111	−178.7 (4)
C7—C5—C6—C10	−1.4 (5)	C109—C110—C111—C112	178.8 (4)
C2—C1—C6—C5	6.4 (5)	C110—C111—C112—C113	178.0 (4)
S1—C1—C6—C5	−170.7 (3)	C111—C112—C113—C114	−179.4 (4)
C2—C1—C6—C10	−177.2 (4)	C21N—N2—C201—C202	−66.4 (4)
S1—C1—C6—C10	5.7 (6)	C22N—N2—C201—C202	56.0 (5)
C4—C5—C7—C8	177.9 (4)	C23N—N2—C201—C202	174.7 (3)
C6—C5—C7—C8	−4.2 (7)	N2—C201—C202—C203	165.4 (3)
C5—C7—C8—C9	5.3 (7)	C201—C202—C203—C204	−177.8 (4)
C7—C8—C9—O3	178.6 (4)	C202—C203—C204—C205	171.9 (4)
C7—C8—C9—C10	−0.7 (7)	C203—C204—C205—C206	−174.7 (4)
N4—N3—C10—C9	10.3 (5)	C204—C205—C206—C207	173.1 (4)
N4—N3—C10—C6	−176.3 (3)	C205—C206—C207—C208	177.3 (4)
O3—C9—C10—N3	−11.1 (6)	C206—C207—C208—C209	177.0 (4)
C8—C9—C10—N3	168.3 (4)	C207—C208—C209—C210	−177.8 (4)
O3—C9—C10—C6	175.8 (4)	C208—C209—C210—C211	−177.9 (4)
C8—C9—C10—C6	−4.9 (6)	C209—C210—C211—C212	178.4 (4)
C5—C6—C10—N3	−167.8 (4)	C210—C211—C212—C213	−178.2 (4)
C1—C6—C10—N3	15.8 (6)	C211—C212—C213—C214	179.6 (4)
C5—C6—C10—C9	5.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O3	1.01 (1)	1.73 (3)	2.480 (4)	128 (3)