Thia­minium dipicrate

In the title mol­ecular structure, C₁₂H₁₈N₄OS²⁺·2C₆H₂N₃O₇^-, the thia­zolium ring bearing the hydr­oxyethyl side chain is disordered over two sites about the methyl­ene bridge. In the minor occupancy component, the dihedral angles are quite different from the range observed in related structures. In the crystal structure, the thia­minium cation and one of the picrate anions form a centrosymmetric hydrogen-bonded cluster. Both anions form `anionic holes' with the thia­minium cation.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.067
• wR factor = 0.240
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for       C141

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for       C142

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          2
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       S111
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C7
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C131
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C101

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        N13

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT430_ALERT_2_B Short Inter D...A Contact  O14    ..  O161    ..       2.83 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O15    ..  N82     ..       2.86 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.01
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT213_ALERT_2_C Atom O151    has ADP max/min Ratio .............       3.20 prolat
PLAT213_ALERT_2_C Atom O152    has ADP max/min Ratio .............       3.20 prolat
PLAT213_ALERT_2_C Atom C192    has ADP max/min Ratio .............       3.80 prolat
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.50 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       S112
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C132
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C91

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N82

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C92

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N11

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N12

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N21

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N22

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N23

Author Response: As the end terminal oxygen, it has large high Ueq value. As well it is in disordered state. So, the comparision of this Carbon with that atom can be overlooked.

PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.00
PLAT301_ALERT_3_C Main Residue  Disorder .........................      18.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT414_ALERT_2_C Short Intra D-H..H-X       H4B    ..  H7B     ..       1.91 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O21    ..  C6      ..       2.99 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O24    ..  C13     ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6     ..  O21     ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12A   ..  O12     ..       2.65 Ang.

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

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

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Thiaminium dipicrate

Crystal data

C12H18N4OS^2+·2C6H2N3O7^−	Z = 2
Mr = 722.58	F(000) = 744
Triclinic, P1	Dx = 1.594 Mg m^−3 Dm = 1.59 Mg m^−3 Dm measured by flotation using a liquid mixture of bromoform and xylene
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.269 (3) Å	Cell parameters from 25 reflections
b = 12.252 (4) Å	θ = 10.4–14.8°
c = 16.641 (3) Å	µ = 0.20 mm^−1
α = 69.35 (4)°	T = 293 K
β = 86.35 (5)°	Needle, yellow
γ = 72.82 (3)°	0.20 × 0.17 × 0.15 mm
V = 1505.6 (9) Å^3

Data collection

Nonius MACH3 sealed-tube diffractometer	2399 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.02
Graphite monochromator	θmax = 25°, θmin = 2.6°
ω–2θ scans	h = −1→8
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
Tmin = 0.946, Tmax = 0.960	l = −19→19
6473 measured reflections	3 standard reflections every 60 min
5276 independent reflections	intensity decay: none

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.240	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1133P)^2 + 0.9209P] where P = (Fo^2 + 2Fc^2)/3
5276 reflections	(Δ/σ)max = 0.003
518 parameters	Δρmax = 0.54 e Å^−3
5 restraints	Δρmin = −0.29 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)
C11	0.4718 (6)	0.2789 (4)	0.9949 (3)	0.0506 (11)
C12	0.6050 (6)	0.3123 (4)	0.9421 (3)	0.0535 (11)
C13	0.5930 (7)	0.4295 (5)	0.8901 (3)	0.0617 (13)
H13	0.6835	0.4461	0.8569	0.074*
C14	0.4491 (7)	0.5228 (4)	0.8862 (3)	0.0631 (14)
C15	0.3172 (7)	0.4999 (4)	0.9368 (3)	0.0598 (13)
H15	0.2213	0.5634	0.9362	0.072*
C16	0.3282 (6)	0.3839 (4)	0.9878 (3)	0.0541 (12)
N11	0.7614 (6)	0.2191 (5)	0.9417 (3)	0.0717 (12)
N12	0.4363 (10)	0.6446 (5)	0.8272 (4)	0.0975 (18)
N13	0.1842 (6)	0.3632 (5)	1.0386 (4)	0.0782 (13)
O11	0.4731 (4)	0.1726 (3)	1.0432 (2)	0.0651 (9)
O12	0.7596 (6)	0.1137 (4)	0.9661 (3)	0.1257 (19)
O13	0.8841 (5)	0.2498 (5)	0.9138 (3)	0.1103 (16)
O14	0.5477 (9)	0.6596 (5)	0.7765 (4)	0.154 (3)
O15	0.3122 (8)	0.7277 (4)	0.8310 (3)	0.129 (2)
O16	0.1173 (10)	0.4278 (9)	1.0811 (7)	0.111 (3)	0.65
O161	0.198 (2)	0.351 (2)	1.1126 (12)	0.134 (7)	0.35
O17	0.1080 (8)	0.3034 (7)	1.0261 (4)	0.163 (3)
C21	0.7765 (6)	0.4738 (5)	0.5052 (3)	0.0691 (15)
C22	0.6985 (6)	0.4239 (5)	0.4565 (3)	0.0685 (14)
C23	0.5852 (6)	0.4936 (5)	0.3889 (3)	0.0707 (15)
H23	0.5379	0.4568	0.3602	0.085*
C24	0.5403 (6)	0.6200 (5)	0.3630 (3)	0.0675 (15)
C25	0.6079 (6)	0.6758 (5)	0.4047 (3)	0.0708 (15)
H25	0.5782	0.7604	0.3867	0.085*
C26	0.7200 (6)	0.6052 (5)	0.4733 (3)	0.0687 (14)
N21	0.7391 (9)	0.2910 (5)	0.4802 (4)	0.106 (2)
N22	0.4132 (6)	0.6924 (6)	0.2930 (3)	0.0880 (16)
N23	0.7792 (7)	0.6717 (6)	0.5163 (4)	0.0991 (16)
O21	0.8819 (5)	0.4105 (4)	0.5659 (2)	0.0973 (14)
O22	0.8059 (8)	0.2272 (5)	0.5500 (4)	0.153 (2)
O23	0.6506 (17)	0.2455 (10)	0.4424 (8)	0.124 (4)	0.55
O231	0.775 (2)	0.2640 (14)	0.4225 (13)	0.148 (6)	0.45
O24	0.3423 (6)	0.6395 (5)	0.2637 (3)	0.1163 (18)
O25	0.3846 (7)	0.8034 (5)	0.2682 (3)	0.134 (2)
O26	0.7734 (8)	0.7784 (5)	0.4744 (4)	0.1342 (19)
O27	0.8380 (8)	0.6208 (5)	0.5891 (3)	0.145 (2)
N1	−0.0408 (5)	0.6618 (3)	0.2815 (2)	0.0536 (10)
H1	0.0289	0.6052	0.3212	0.064*
C2	−0.1235 (6)	0.6316 (4)	0.2297 (3)	0.0493 (11)
C3	−0.0845 (7)	0.4997 (4)	0.2418 (3)	0.0717 (15)
H3B	−0.1878	0.4811	0.2376	0.108*
H3A	−0.0299	0.4511	0.2975	0.108*
H3C	−0.0106	0.4822	0.1982	0.108*
N3	−0.2338 (5)	0.7143 (3)	0.1700 (2)	0.0523 (9)
C4	−0.2608 (6)	0.8335 (4)	0.1583 (3)	0.0521 (11)
N4	−0.3703 (5)	0.9128 (3)	0.0954 (3)	0.0785 (14)
H4A	−0.4199	0.8876	0.0646	0.094*
H4B	−0.3920	0.9897	0.0853	0.094*
C5	−0.1737 (6)	0.8693 (4)	0.2101 (3)	0.0610 (13)
C6	−0.0648 (6)	0.7790 (4)	0.2724 (3)	0.0642 (14)
H6	−0.0063	0.7981	0.3091	0.077*
C7	−0.2106 (9)	1.0025 (5)	0.1960 (5)	0.112 (3)
H7A	−0.2921	1.0240	0.2365	0.134*	0.54
H7B	−0.2589	1.0510	0.1383	0.134*	0.54
H7C	−0.1827	1.0448	0.1381	0.134*	0.46
H7D	−0.3311	1.0360	0.2012	0.134*	0.46
N81	−0.042 (3)	1.0303 (10)	0.2087 (10)	0.084 (6)	0.54
C91	−0.0251 (16)	1.0448 (8)	0.2891 (8)	0.054 (2)	0.54
C191	−0.150 (3)	1.0251 (19)	0.3582 (11)	0.083 (7)*	0.54
H19A	−0.2427	1.0086	0.3377	0.125*	0.54
H19B	−0.1913	1.0970	0.3732	0.125*	0.54
H19C	−0.0952	0.9571	0.4079	0.125*	0.54
C101	0.110 (2)	1.0726 (17)	0.2985 (12)	0.053 (6)*	0.54
S111	0.2275 (5)	1.0886 (3)	0.2078 (2)	0.0975 (10)	0.54
C121	0.073 (3)	1.0549 (18)	0.155 (2)	0.078 (5)	0.54
H12A	0.0764	1.0552	0.0988	0.093*	0.54
C131	0.1618 (13)	1.1037 (13)	0.3725 (9)	0.110 (3)	0.54
H13A	0.1341	1.1917	0.3553	0.132*	0.54
H13B	0.0956	1.0758	0.4216	0.132*	0.54
C141	0.3411 (14)	1.0506 (11)	0.3989 (9)	0.099 (4)	0.54
H14A	0.3776	1.0959	0.4280	0.118*	0.54
H14B	0.3651	0.9660	0.4365	0.118*	0.54
O151	0.418 (3)	1.061 (4)	0.3216 (12)	0.54 (3)	0.54
N82	−0.1140 (18)	1.0269 (9)	0.2576 (10)	0.060 (3)	0.46
C92	0.031 (2)	1.0444 (13)	0.2327 (13)	0.062 (4)	0.46
C192	0.130 (4)	1.036 (3)	0.157 (2)	0.109 (12)	0.46
H19D	0.0766	1.0035	0.1250	0.164*	0.46
H19E	0.2428	0.9827	0.1758	0.164*	0.46
H19F	0.1358	1.1154	0.1213	0.164*	0.46
C102	0.111 (4)	1.080 (3)	0.2845 (18)	0.082 (11)*	0.46
S112	−0.0236 (5)	1.0763 (4)	0.3756 (2)	0.0937 (11)	0.46
C122	−0.166 (2)	1.0405 (19)	0.3300 (13)	0.072 (5)	0.46
H12B	−0.2685	1.0315	0.3533	0.087*	0.46
C132	0.2670 (17)	1.1170 (15)	0.2873 (8)	0.110 (3)	0.46
H13C	0.2176	1.2040	0.2742	0.132*	0.46
H13D	0.3174	1.1101	0.2344	0.132*	0.46
C142	0.4283 (18)	1.0933 (14)	0.3419 (10)	0.099 (4)	0.46
H14C	0.5309	1.0601	0.3162	0.118*	0.46
H14D	0.4337	1.1671	0.3495	0.118*	0.46
O152	0.401 (5)	1.007 (4)	0.4204 (16)	0.54 (3)	0.46
H151	0.4587	1.1411	0.3194	0.050*	0.54
H152	0.5373	0.9543	0.4237	0.050*	0.46

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.056 (3)	0.042 (3)	0.052 (3)	−0.006 (2)	−0.012 (2)	−0.018 (2)
C12	0.059 (3)	0.048 (3)	0.051 (3)	−0.007 (2)	−0.007 (2)	−0.019 (2)
C13	0.073 (3)	0.063 (3)	0.054 (3)	−0.031 (3)	−0.005 (2)	−0.017 (2)
C14	0.079 (4)	0.041 (3)	0.064 (3)	−0.016 (3)	−0.024 (3)	−0.010 (2)
C15	0.069 (3)	0.041 (3)	0.066 (3)	−0.003 (2)	−0.021 (3)	−0.021 (2)
C16	0.057 (3)	0.051 (3)	0.055 (3)	−0.009 (2)	−0.005 (2)	−0.023 (2)
N11	0.069 (3)	0.075 (3)	0.058 (3)	−0.002 (3)	0.002 (2)	−0.022 (2)
N12	0.135 (5)	0.055 (3)	0.088 (4)	−0.036 (4)	−0.035 (4)	0.005 (3)
N13	0.068 (3)	0.072 (3)	0.090 (4)	−0.012 (3)	−0.001 (3)	−0.029 (3)
O11	0.074 (2)	0.0423 (18)	0.067 (2)	−0.0082 (16)	−0.0055 (17)	−0.0107 (16)
O12	0.120 (4)	0.065 (3)	0.150 (4)	0.011 (3)	0.050 (3)	−0.026 (3)
O13	0.060 (3)	0.132 (4)	0.140 (4)	−0.026 (3)	0.006 (3)	−0.049 (3)
O14	0.179 (6)	0.093 (4)	0.152 (5)	−0.067 (4)	0.000 (4)	0.026 (3)
O15	0.166 (5)	0.042 (2)	0.148 (5)	−0.005 (3)	−0.051 (4)	−0.007 (3)
O16	0.074 (6)	0.146 (8)	0.115 (7)	0.003 (5)	0.015 (5)	−0.079 (6)
O161	0.097 (13)	0.20 (2)	0.086 (12)	−0.009 (12)	0.025 (10)	−0.053 (13)
O17	0.132 (5)	0.243 (8)	0.179 (6)	−0.120 (5)	0.064 (4)	−0.107 (6)
C21	0.053 (3)	0.080 (4)	0.044 (3)	0.004 (3)	0.003 (2)	−0.005 (3)
C22	0.059 (3)	0.076 (4)	0.053 (3)	0.005 (3)	0.005 (3)	−0.022 (3)
C23	0.056 (3)	0.092 (4)	0.052 (3)	−0.002 (3)	0.002 (2)	−0.028 (3)
C24	0.049 (3)	0.086 (4)	0.039 (2)	0.003 (3)	−0.003 (2)	−0.005 (3)
C25	0.062 (3)	0.071 (3)	0.053 (3)	−0.003 (3)	0.002 (3)	−0.005 (3)
C26	0.057 (3)	0.087 (4)	0.052 (3)	−0.013 (3)	−0.006 (3)	−0.017 (3)
N21	0.106 (5)	0.083 (4)	0.092 (4)	0.018 (4)	0.003 (4)	−0.024 (4)
N22	0.063 (3)	0.117 (5)	0.050 (3)	0.006 (3)	−0.007 (2)	−0.012 (3)
N23	0.097 (4)	0.102 (4)	0.088 (4)	−0.027 (4)	−0.013 (3)	−0.020 (3)
O21	0.085 (3)	0.110 (3)	0.055 (2)	0.009 (2)	−0.026 (2)	−0.005 (2)
O22	0.155 (5)	0.086 (3)	0.160 (5)	−0.009 (3)	−0.047 (4)	0.012 (4)
O23	0.163 (11)	0.100 (7)	0.124 (8)	−0.031 (8)	−0.018 (8)	−0.058 (6)
O231	0.163 (15)	0.104 (10)	0.193 (16)	−0.029 (10)	0.053 (12)	−0.086 (10)
O24	0.091 (3)	0.174 (5)	0.070 (3)	−0.008 (3)	−0.025 (2)	−0.047 (3)
O25	0.123 (4)	0.112 (4)	0.097 (3)	0.010 (3)	−0.041 (3)	0.016 (3)
O26	0.160 (5)	0.109 (4)	0.137 (4)	−0.045 (4)	−0.017 (4)	−0.038 (4)
O27	0.200 (6)	0.152 (5)	0.084 (3)	−0.058 (4)	−0.054 (4)	−0.024 (3)
N1	0.051 (2)	0.046 (2)	0.050 (2)	0.0017 (17)	−0.0120 (18)	−0.0118 (17)
C2	0.053 (3)	0.045 (2)	0.040 (2)	−0.006 (2)	−0.005 (2)	−0.0092 (19)
C3	0.100 (4)	0.044 (3)	0.062 (3)	−0.012 (3)	−0.011 (3)	−0.013 (2)
N3	0.060 (2)	0.044 (2)	0.044 (2)	−0.0075 (18)	−0.0117 (18)	−0.0091 (16)
C4	0.057 (3)	0.045 (3)	0.046 (2)	−0.007 (2)	−0.012 (2)	−0.010 (2)
N4	0.102 (3)	0.044 (2)	0.080 (3)	−0.013 (2)	−0.053 (3)	−0.007 (2)
C5	0.072 (3)	0.043 (3)	0.061 (3)	−0.005 (2)	−0.024 (3)	−0.015 (2)
C6	0.068 (3)	0.053 (3)	0.068 (3)	−0.001 (2)	−0.030 (3)	−0.024 (2)
C7	0.123 (5)	0.056 (3)	0.150 (6)	0.005 (3)	−0.096 (5)	−0.037 (4)
N81	0.140 (15)	0.039 (5)	0.059 (10)	0.006 (7)	−0.051 (12)	−0.018 (6)
C91	0.055 (7)	0.046 (5)	0.063 (7)	−0.010 (4)	−0.012 (7)	−0.022 (5)
S111	0.100 (2)	0.094 (2)	0.088 (2)	−0.0327 (19)	0.0315 (19)	−0.0207 (17)
C121	0.079 (16)	0.059 (9)	0.059 (10)	0.013 (11)	−0.007 (12)	−0.004 (8)
C131	0.095 (7)	0.154 (9)	0.105 (7)	−0.047 (7)	−0.007 (6)	−0.062 (7)
C141	0.102 (9)	0.069 (6)	0.124 (10)	−0.036 (5)	−0.047 (7)	−0.014 (6)
O151	0.44 (3)	0.52 (5)	0.51 (5)	−0.20 (3)	−0.36 (4)	0.10 (4)
N82	0.081 (10)	0.046 (5)	0.049 (8)	−0.012 (5)	−0.029 (7)	−0.012 (5)
C92	0.074 (10)	0.059 (8)	0.034 (8)	0.002 (7)	−0.007 (9)	−0.012 (6)
C192	0.09 (2)	0.112 (16)	0.049 (10)	0.071 (11)	−0.027 (12)	−0.016 (10)
S112	0.090 (2)	0.136 (3)	0.074 (2)	−0.036 (2)	−0.0007 (18)	−0.054 (2)
C122	0.053 (9)	0.104 (12)	0.058 (11)	−0.026 (7)	−0.012 (9)	−0.021 (9)
C132	0.095 (7)	0.154 (9)	0.105 (7)	−0.047 (7)	−0.007 (6)	−0.062 (7)
C142	0.102 (9)	0.069 (6)	0.124 (10)	−0.036 (5)	−0.047 (7)	−0.014 (6)
O152	0.44 (3)	0.52 (5)	0.51 (5)	−0.20 (3)	−0.36 (4)	0.10 (4)

Geometric parameters (Å, º)

C11—O11	1.263 (5)	C4—C5	1.410 (6)
C11—C12	1.430 (6)	N4—H4A	0.8600
C11—C16	1.445 (6)	N4—H4B	0.8600
C12—C13	1.368 (6)	C5—C6	1.353 (6)
C12—N11	1.451 (6)	C5—C7	1.502 (7)
C13—C14	1.371 (7)	C6—H6	0.9300
C13—H13	0.9300	C7—N82	1.496 (18)
C14—C15	1.369 (7)	C7—N81	1.57 (2)
C14—N12	1.445 (7)	C7—H7A	0.9700
C15—C16	1.354 (6)	C7—H7B	0.9700
C15—H15	0.9300	C7—H7C	0.9700
C16—N13	1.448 (7)	C7—H7D	0.9700
N11—O13	1.196 (5)	N81—C121	1.30 (4)
N11—O12	1.214 (6)	N81—C91	1.432 (16)
N12—O14	1.219 (8)	C91—C101	1.29 (3)
N12—O15	1.230 (7)	C91—C191	1.50 (2)
N13—O17	1.173 (7)	C191—H19A	0.9600
N13—O161	1.196 (18)	C191—H19B	0.9600
N13—O16	1.233 (9)	C191—H19C	0.9600
O16—O161	0.965 (18)	C101—C131	1.53 (2)
C21—O21	1.242 (6)	C101—S111	1.73 (2)
C21—C26	1.441 (7)	S111—C121	1.81 (3)
C21—C22	1.447 (8)	C121—H12A	0.9300
C22—C23	1.362 (7)	C131—C141	1.458 (9)
C22—N21	1.469 (8)	C131—H13A	0.9700
C23—C24	1.390 (7)	C131—H13B	0.9700
C23—H23	0.9300	C141—O151	1.380 (10)
C24—C25	1.367 (8)	C141—H14A	0.9700
C24—N22	1.459 (6)	C141—H14B	0.9700
C25—C26	1.370 (7)	O151—H151	1.12 (4)
C25—H25	0.9300	N82—C92	1.30 (2)
C26—N23	1.453 (8)	N82—C122	1.30 (3)
N21—O231	1.119 (18)	C92—C102	1.37 (4)
N21—O22	1.205 (7)	C92—C192	1.48 (4)
N21—O23	1.338 (12)	C192—H19D	0.9600
N22—O24	1.218 (7)	C192—H19E	0.9600
N22—O25	1.226 (7)	C192—H19F	0.9600
N23—O27	1.206 (6)	C102—C132	1.50 (3)
N23—O26	1.234 (7)	C102—S112	1.82 (3)
O23—O231	1.125 (16)	S112—C122	1.675 (17)
N1—C2	1.340 (5)	C122—H12B	0.9300
N1—C6	1.345 (5)	C132—C142	1.557 (9)
N1—H1	0.8600	C132—H13C	0.9700
C2—N3	1.305 (5)	C132—H13D	0.9700
C2—C3	1.492 (6)	C142—O152	1.417 (10)
C3—H3B	0.9600	C142—H14C	0.9700
C3—H3A	0.9600	C142—H14D	0.9700
C3—H3C	0.9600	C142—H151	0.682 (14)
N3—C4	1.354 (5)	O152—H152	1.11 (5)
C4—N4	1.319 (5)
O11—C11—C12	126.5 (4)	N82—C7—C5	113.5 (5)
O11—C11—C16	121.9 (4)	C5—C7—N81	109.6 (6)
C12—C11—C16	111.6 (4)	C5—C7—H7A	109.8
C13—C12—C11	123.2 (5)	N81—C7—H7A	109.8
C13—C12—N11	117.2 (5)	N82—C7—H7B	132.6
C11—C12—N11	119.6 (4)	C5—C7—H7B	109.8
C12—C13—C14	120.8 (5)	N81—C7—H7B	109.8
C12—C13—H13	119.6	H7A—C7—H7B	108.2
C14—C13—H13	119.6	N82—C7—H7C	108.3
C15—C14—C13	120.0 (4)	C5—C7—H7C	109.3
C15—C14—N12	120.3 (5)	N81—C7—H7C	76.0
C13—C14—N12	119.6 (6)	H7A—C7—H7C	135.3
C16—C15—C14	119.2 (5)	N82—C7—H7D	109.3
C16—C15—H15	120.4	C5—C7—H7D	108.6
C14—C15—H15	120.4	N81—C7—H7D	137.6
C15—C16—C11	125.1 (5)	H7B—C7—H7D	73.1
C15—C16—N13	117.4 (5)	H7C—C7—H7D	107.7
C11—C16—N13	117.5 (4)	C121—N81—C91	115 (2)
O13—N11—O12	122.8 (5)	C121—N81—C7	130.2 (19)
O13—N11—C12	118.7 (5)	C91—N81—C7	114.3 (19)
O12—N11—C12	118.4 (5)	C101—C91—N81	114.6 (19)
O14—N12—O15	123.6 (6)	C101—C91—C191	122.5 (14)
O14—N12—C14	118.7 (7)	N81—C91—C191	122.9 (17)
O15—N12—C14	117.7 (7)	C91—C191—H19A	109.5
O17—N13—O161	114.2 (13)	C91—C191—H19B	109.5
O17—N13—O16	117.6 (7)	H19A—C191—H19B	109.5
O17—N13—C16	119.9 (5)	C91—C191—H19C	109.5
O161—N13—C16	115.5 (10)	H19A—C191—H19C	109.5
O16—N13—C16	120.6 (7)	H19B—C191—H19C	109.5
O21—C21—C26	124.4 (6)	C91—C101—C131	128.7 (16)
O21—C21—C22	123.8 (5)	C91—C101—S111	111.3 (14)
C26—C21—C22	111.8 (4)	C131—C101—S111	119.7 (13)
C23—C22—C21	123.6 (5)	C101—S111—C121	90.7 (13)
C23—C22—N21	116.7 (6)	N81—C121—S111	108 (2)
C21—C22—N21	119.7 (5)	N81—C121—H12A	126.0
C22—C23—C24	119.8 (6)	S111—C121—H12A	126.0
C22—C23—H23	120.1	C141—C131—C101	114.4 (12)
C24—C23—H23	120.1	C141—C131—H13A	108.7
C25—C24—C23	120.9 (5)	C101—C131—H13A	108.7
C25—C24—N22	120.4 (6)	C141—C131—H13B	108.7
C23—C24—N22	118.6 (6)	C101—C131—H13B	108.7
C24—C25—C26	119.0 (5)	H13A—C131—H13B	107.6
C24—C25—H25	120.5	O151—C141—C131	102.5 (15)
C26—C25—H25	120.5	O151—C141—H14A	111.3
C25—C26—C21	124.8 (5)	C131—C141—H14A	111.3
C25—C26—N23	115.3 (5)	O151—C141—H14B	111.3
C21—C26—N23	119.8 (5)	C131—C141—H14B	111.3
O231—N21—O22	121.1 (12)	H14A—C141—H14B	109.2
O22—N21—O23	117.8 (8)	C141—O151—H151	94 (2)
O231—N21—C22	110.5 (10)	C92—N82—C122	117 (2)
O22—N21—C22	118.3 (7)	C92—N82—C7	115.8 (19)
O23—N21—C22	119.3 (7)	C122—N82—C7	126.7 (14)
O24—N22—O25	124.6 (5)	N82—C92—C102	116 (3)
O24—N22—C24	118.5 (6)	N82—C92—C192	133 (3)
O25—N22—C24	116.9 (6)	C102—C92—C192	111 (2)
O27—N23—O26	122.5 (7)	C92—C192—H19D	109.5
O27—N23—C26	120.0 (6)	C92—C192—H19E	109.5
O26—N23—C26	117.4 (5)	H19D—C192—H19E	109.5
O231—O23—N21	53.2 (11)	C92—C192—H19F	109.5
C2—N1—C6	121.2 (4)	H19D—C192—H19F	109.5
C2—N1—H1	119.4	H19E—C192—H19F	109.5
C6—N1—H1	119.4	C92—C102—C132	140 (2)
N3—C2—N1	121.5 (4)	C92—C102—S112	104.5 (19)
N3—C2—C3	120.7 (4)	C132—C102—S112	115.7 (19)
N1—C2—C3	117.8 (4)	C122—S112—C102	91.0 (12)
C2—C3—H3B	109.5	N82—C122—S112	111.1 (14)
C2—C3—H3A	109.5	N82—C122—H12B	124.5
H3B—C3—H3A	109.5	S112—C122—H12B	124.5
C2—C3—H3C	109.5	C102—C132—C142	145.3 (15)
H3B—C3—H3C	109.5	C102—C132—H13C	100.5
H3A—C3—H3C	109.5	C142—C132—H13C	100.5
C2—N3—C4	119.2 (4)	C102—C132—H13D	100.5
N4—C4—N3	116.3 (4)	C142—C132—H13D	100.5
N4—C4—C5	122.6 (4)	H13C—C132—H13D	104.3
N3—C4—C5	121.1 (4)	O152—C142—C132	101.1 (7)
C4—N4—H4A	120.0	O152—C142—H14C	111.6
C4—N4—H4B	120.0	C132—C142—H14C	111.6
H4A—N4—H4B	120.0	O152—C142—H14D	111.6
C6—C5—C4	116.8 (4)	C132—C142—H14D	111.6
C6—C5—C7	123.9 (4)	H14C—C142—H14D	109.4
C4—C5—C7	119.2 (4)	O152—C142—H151	151 (2)
N1—C6—C5	120.2 (4)	C132—C142—H151	103.3 (14)
N1—C6—H6	119.9	H14C—C142—H151	73.4
C5—C6—H6	119.9	C142—O152—H152	89 (2)
O11—C11—C12—C13	178.8 (4)	C21—C26—N23—O26	157.9 (6)
C16—C11—C12—C13	−1.6 (6)	O22—N21—O23—O231	−109.7 (15)
O11—C11—C12—N11	−0.6 (7)	C22—N21—O23—O231	94.9 (14)
C16—C11—C12—N11	179.0 (4)	O22—N21—O231—O23	103.4 (15)
C11—C12—C13—C14	0.1 (7)	C22—N21—O231—O23	−111.9 (11)
N11—C12—C13—C14	179.5 (4)	C6—N1—C2—N3	−1.9 (7)
C12—C13—C14—C15	2.1 (7)	C6—N1—C2—C3	177.6 (4)
C12—C13—C14—N12	−176.6 (4)	N1—C2—N3—C4	2.3 (7)
C13—C14—C15—C16	−2.7 (7)	C3—C2—N3—C4	−177.1 (4)
N12—C14—C15—C16	176.1 (4)	C2—N3—C4—N4	178.2 (4)
C14—C15—C16—C11	1.1 (7)	C2—N3—C4—C5	−0.9 (7)
C14—C15—C16—N13	−178.4 (4)	N4—C4—C5—C6	180.0 (5)
O11—C11—C16—C15	−179.3 (4)	N3—C4—C5—C6	−1.0 (7)
C12—C11—C16—C15	1.0 (6)	N4—C4—C5—C7	2.4 (8)
O11—C11—C16—N13	0.2 (6)	N3—C4—C5—C7	−178.6 (5)
C12—C11—C16—N13	−179.5 (4)	C2—N1—C6—C5	−0.1 (7)
C13—C12—N11—O13	17.4 (7)	C4—C5—C6—N1	1.5 (8)
C11—C12—N11—O13	−163.1 (5)	C7—C5—C6—N1	179.0 (6)
C13—C12—N11—O12	−159.1 (5)	C6—C5—C7—N82	0.4 (11)
C11—C12—N11—O12	20.4 (7)	C4—C5—C7—N82	177.8 (8)
C15—C14—N12—O14	−172.2 (6)	C6—C5—C7—N81	39.9 (11)
C13—C14—N12—O14	6.6 (8)	C4—C5—C7—N81	−142.7 (8)
C15—C14—N12—O15	7.7 (7)	N82—C7—N81—C121	−171 (2)
C13—C14—N12—O15	−173.5 (5)	C5—C7—N81—C121	85.3 (2)
C15—C16—N13—O17	116.2 (7)	N82—C7—N81—C91	0.3 (7)
C11—C16—N13—O17	−63.3 (7)	C5—C7—N81—C91	−103.0 (9)
C15—C16—N13—O161	−100.9 (14)	C121—N81—C91—C101	−4.3 (18)
C11—C16—N13—O161	79.6 (14)	C7—N81—C91—C101	−177.3 (11)
C15—C16—N13—O16	−47.7 (9)	C121—N81—C91—C191	177.7 (15)
C11—C16—N13—O16	132.8 (8)	C7—N81—C91—C191	4.7 (15)
O17—N13—O16—O161	98.3 (18)	N81—C91—C101—C131	175.1 (15)
C16—N13—O16—O161	−97.4 (17)	C191—C91—C101—C131	−7 (3)
O17—N13—O161—O16	−105.9 (16)	N81—C91—C101—S111	1.8 (16)
C16—N13—O161—O16	109.1 (13)	C191—C91—C101—S111	179.8 (12)
O21—C21—C22—C23	−178.8 (5)	C91—C101—S111—C121	0.5 (13)
C26—C21—C22—C23	−0.2 (7)	C131—C101—S111—C121	−173.5 (14)
O21—C21—C22—N21	2.2 (8)	C91—N81—C121—S111	4.4 (16)
C26—C21—C22—N21	−179.3 (5)	C7—N81—C121—S111	176.0 (9)
C21—C22—C23—C24	0.7 (8)	C101—S111—C121—N81	−2.9 (13)
N21—C22—C23—C24	179.8 (5)	C91—C101—C131—C141	139.0 (16)
C22—C23—C24—C25	−0.3 (8)	S111—C101—C131—C141	−48.1 (2)
C22—C23—C24—N22	−177.4 (4)	C101—C131—C141—O151	38 (2)
C23—C24—C25—C26	−0.6 (8)	C5—C7—N82—C92	91.2 (10)
N22—C24—C25—C26	176.4 (4)	N81—C7—N82—C92	−0.5 (11)
C24—C25—C26—C21	1.2 (8)	C5—C7—N82—C122	−93.8 (2)
C24—C25—C26—N23	−177.1 (5)	N81—C7—N82—C122	175 (2)
O21—C21—C26—C25	177.8 (5)	C122—N82—C92—C102	−2 (2)
C22—C21—C26—C25	−0.7 (7)	C7—N82—C92—C102	173.2 (15)
O21—C21—C26—N23	−4.0 (8)	C122—N82—C92—C192	179 (2)
C22—C21—C26—N23	177.5 (5)	C7—N82—C92—C192	−6 (2)
C23—C22—N21—O231	51.2 (15)	N82—C92—C102—C132	−176 (3)
C21—C22—N21—O231	−129.7 (14)	C192—C92—C102—C132	3 (4)
C23—C22—N21—O22	−163.0 (6)	N82—C92—C102—S112	4 (2)
C21—C22—N21—O22	16.1 (9)	C192—C92—C102—S112	−176.9 (15)
C23—C22—N21—O23	−7.7 (1)	C92—C102—S112—C122	−3.7 (17)
C21—C22—N21—O23	171.3 (1)	C132—C102—S112—C122	176.4 (19)
C25—C24—N22—O24	−172.0 (5)	C92—N82—C122—S112	−1.1 (18)
C23—C24—N22—O24	5.1 (7)	C7—N82—C122—S112	−176.0 (8)
C25—C24—N22—O25	7.4 (8)	C102—S112—C122—N82	2.8 (16)
C23—C24—N22—O25	−175.5 (5)	C92—C102—C132—C142	−128 (3)
C25—C26—N23—O27	159.4 (6)	S112—C102—C132—C142	52 (4)
C21—C26—N23—O27	−18.9 (9)	C102—C132—C142—O152	−6 (4)
C25—C26—N23—O26	−23.7 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O12^i	0.86	2.55	3.062 (7)	119
N4—H4B···O11^i	0.86	2.07	2.885 (5)	159
N4—H4A···O11^ii	0.86	2.28	3.102 (5)	161
N1—H1···O27^iii	0.86	2.57	3.348 (7)	151
N1—H1···O21^iii	0.86	1.99	2.667 (5)	135
O151—H151···O14^iv	1.12 (4)	2.387 (5)	3.33 (4)	140.1 (1)
O152—H152···O26	1.11 (5)	2.369 (6)	3.40 (5)	154.4 (1)
C6—H6···O21^iii	0.93	2.62	2.993 (6)	104
C3—H3A···O27^iii	0.96	2.29	3.205 (7)	159
C3—H3C···O16^v	0.96	2.37	3.307 (10)	167
C121—H12A···O12^iii	0.93	2.65	3.33 (3)	131
C122—H12B···O151^vi	0.93	2.58	3.39 (3)	146

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