l-Leucine l-leucinium picrate

Anitha, K.; Athimoolam, S.; Rajaram, R.K.

doi:10.1107/S1600536805014030

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L-Leucine L-leucinium picrate

K. Anitha, S. Athimoolam and R. K. Rajaram

The asymmetric unit of the title compound, C₆H₁₃NO₂·C₆H₁₄NO₂⁺·C₆H₂N₃O₇^-, contains two unprotonated leucine residues, two protonated leucinium cations and two picrate anions. The leucine residues show a class II hydrogen-bonding scheme and the leucinium residues show a class I hydrogen-bonding scheme. The leucine and leucinium residues form infinite hydrogen-bonded chains running along the a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014030/bt6660sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014030/bt6660Isup2.hkl Contains datablock I

CCDC reference: 274341

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R factor = 0.051
wR factor = 0.149
Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.
PLAT223_ALERT_4_B Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       4.81 Ratio
PLAT231_ALERT_4_B Hirshfeld Test (Solvent)   C24    -   C25     ..      12.11 su
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        N11

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.21
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT221_ALERT_4_C Large Solvent/Anion  C     Ueq(max)/Ueq(min) ...       3.85 Ratio
PLAT221_ALERT_4_C Large Solvent/Anion  C     Ueq(max)/Ueq(min) ...       3.14 Ratio
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT223_ALERT_4_C Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       3.90 Ratio
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C24    -   C26     ..       5.28 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C33    -   C34     ..       6.09 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C34
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C54
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C24
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C33
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.37
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.18
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C34    -   C35    ...       1.41 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H31B   ..  O12     ..       2.62 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C18 H29 N5 O11
            Atom count from _chemical_formula_moiety:C.072 H.09 N.03 O.066
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           24.98
           From the CIF: _reflns_number_total               4392
           Count of symmetry unique reflns         4397
           Completeness (_total/calc)             99.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

Computing details top

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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

L-Leucine L-leucinium picrate top

Crystal data top

C₆H₁₃NO₂·C₆H₁₄NO₂⁺·C₆H₂N₃O₇⁻	Z = 2
M_r = 491.46	F(000) = 520
Triclinic, P1	D_x = 1.306 Mg m⁻³ D_m = 1.297 Mg m⁻³ D_m measured by flotation in a mixture of carbon tetracholride and xylene
a = 7.1470 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.8540 (8) Å	Cell parameters from 25 reflections
c = 15.456 (1) Å	θ = 10.4–13.9°
α = 106.45 (2)°	µ = 0.11 mm⁻¹
β = 95.17 (1)°	T = 293 K
γ = 91.02 (2)°	Plate, yellow
V = 1249.5 (2) Å³	0.25 × 0.15 × 0.12 mm

Data collection top

Nonius MACH3 sealed tube diffractometer	3495 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 25.0°, θ_min = 2.6°
ω–2θ scans	h = −1→8
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
T_min = 0.981, T_max = 0.987	l = −18→18
5538 measured reflections	3 standard reflections every 60 min
4392 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0871P)² + 0.3632P] where P = (F_o² + 2F_c²)/3
4392 reflections	(Δ/σ)_max < 0.001
609 parameters	Δρ_max = 0.38 e Å⁻³
6 restraints	Δρ_min = −0.50 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6176 (7)	0.7671 (4)	0.8035 (3)	0.0417 (11)
C2	0.4548 (7)	0.7822 (4)	0.8537 (3)	0.0433 (11)
C3	0.4338 (7)	0.7357 (5)	0.9250 (3)	0.0462 (12)
H3	0.3256	0.7477	0.9551	0.055*
C4	0.5764 (8)	0.6711 (5)	0.9507 (3)	0.0474 (13)
C5	0.7364 (8)	0.6505 (4)	0.9058 (3)	0.0457 (12)
H5	0.8306	0.6065	0.9240	0.055*
C6	0.7554 (7)	0.6956 (4)	0.8337 (3)	0.0412 (11)
N3	0.3022 (7)	0.8483 (5)	0.8289 (3)	0.0579 (12)
N1	0.9216 (7)	0.6659 (5)	0.7873 (3)	0.0581 (12)
N2	0.5577 (9)	0.6264 (5)	1.0273 (3)	0.0649 (14)
O1	0.6372 (5)	0.8156 (4)	0.7423 (2)	0.0559 (10)
O7	0.2739 (7)	0.8528 (6)	0.7507 (3)	0.0908 (17)
O6	0.2046 (7)	0.8986 (5)	0.8866 (3)	0.0858 (15)
O5	0.4181 (8)	0.6490 (5)	1.0677 (3)	0.0853 (15)
O4	0.6892 (9)	0.5737 (6)	1.0520 (4)	0.1029 (19)
O3	1.0540 (7)	0.6235 (5)	0.8222 (4)	0.0882 (15)
O2	0.9304 (8)	0.6832 (7)	0.7137 (4)	0.116 (2)
C11	0.6452 (7)	0.8929 (4)	0.1905 (3)	0.0421 (11)
C12	0.5065 (7)	0.9652 (5)	0.1574 (3)	0.0451 (12)
C13	0.5272 (8)	1.0089 (5)	0.0865 (3)	0.0480 (12)
H13	0.4326	1.0523	0.0679	0.058*
C14	0.6860 (7)	0.9897 (5)	0.0421 (3)	0.0438 (11)
C15	0.8262 (8)	0.9214 (5)	0.0663 (3)	0.0486 (12)
H15	0.9312	0.9057	0.0341	0.058*
C16	0.8075 (7)	0.8781 (5)	0.1374 (3)	0.0456 (12)
N11	0.3374 (7)	0.9942 (5)	0.2041 (4)	0.0627 (13)
N12	0.7062 (8)	1.0359 (5)	−0.0342 (3)	0.0594 (13)
N13	0.9586 (7)	0.8070 (4)	0.1595 (3)	0.0580 (12)
O11	0.6263 (6)	0.8484 (4)	0.2529 (2)	0.0551 (10)
O12	0.3182 (8)	0.9669 (7)	0.2719 (4)	0.117 (2)
O13	0.2168 (8)	1.0415 (7)	0.1701 (5)	0.119 (2)
O14	0.5792 (8)	1.0890 (5)	−0.0587 (4)	0.0920 (17)
O15	0.8502 (8)	1.0184 (5)	−0.0720 (3)	0.0886 (16)
O16	1.0580 (7)	0.7590 (5)	0.1010 (3)	0.0888 (16)
O17	0.9861 (7)	0.8032 (5)	0.2383 (3)	0.0820 (15)
C21	0.6535 (6)	0.0380 (4)	0.6472 (3)	0.0403 (10)
C22	0.7999 (6)	0.0708 (4)	0.7294 (3)	0.0401 (10)
H22	0.7342	0.0876	0.7844	0.048*
C23	0.9235 (9)	0.1801 (5)	0.7332 (4)	0.0566 (14)
H23A	1.0174	0.1566	0.6907	0.068*
H23B	0.8453	0.2358	0.7133	0.068*
C24	1.0223 (12)	0.2413 (6)	0.8256 (4)	0.080 (2)
H24	1.0679	0.1828	0.8554	0.096*
C25	0.8706 (18)	0.3188 (11)	0.8823 (8)	0.154 (3)
H25A	0.7651	0.3270	0.8419	0.231*
H25B	0.9262	0.3952	0.9145	0.231*
H25C	0.8291	0.2807	0.9249	0.231*
C26	1.181 (2)	0.3242 (10)	0.8235 (8)	0.154 (3)
H26A	1.2548	0.2877	0.7751	0.231*
H26B	1.2586	0.3432	0.8802	0.231*
H26C	1.1314	0.3949	0.8140	0.231*
N21	0.9190 (6)	−0.0321 (4)	0.7267 (3)	0.0456 (10)
H21A	0.8456	−0.0957	0.7213	0.068*
H21B	0.9958	−0.0172	0.7776	0.068*
H21C	0.9865	−0.0449	0.6795	0.068*
O21B	0.5289 (6)	0.1114 (3)	0.6490 (3)	0.0684 (11)
O21A	0.6664 (5)	−0.0557 (3)	0.5861 (2)	0.0454 (8)
C31	0.0903 (7)	0.6128 (4)	0.3338 (3)	0.0439 (11)
C32	0.2107 (6)	0.5778 (4)	0.2540 (3)	0.0405 (10)
H32	0.1276	0.5614	0.1975	0.049*
C33	0.3199 (8)	0.4691 (5)	0.2533 (4)	0.0519 (13)
H33A	0.4177	0.4900	0.3036	0.062*
H33B	0.2353	0.4106	0.2639	0.062*
C34	0.4100 (17)	0.4133 (9)	0.1681 (6)	0.127 (2)
H34	0.4761	0.4773	0.1530	0.153*
C35	0.2847 (17)	0.3577 (9)	0.0917 (6)	0.127 (2)
H35A	0.2075	0.2992	0.1054	0.191*
H35B	0.3547	0.3209	0.0419	0.191*
H35C	0.2064	0.4151	0.0757	0.191*
C36	0.5588 (17)	0.3284 (9)	0.1826 (6)	0.127 (2)
H36A	0.4990	0.2601	0.1918	0.191*
H36B	0.6437	0.3665	0.2350	0.191*
H36C	0.6274	0.3051	0.1303	0.191*
N31	0.3424 (6)	0.6795 (4)	0.2591 (3)	0.0462 (10)
H31A	0.4260	0.6909	0.3074	0.069*
H31B	0.2776	0.7440	0.2638	0.069*
H31C	0.4020	0.6641	0.2092	0.069*
O31B	−0.0397 (6)	0.5388 (3)	0.3302 (3)	0.0732 (12)
O31A	0.1296 (5)	0.7062 (3)	0.3954 (2)	0.0461 (8)
C41	1.1462 (6)	0.0021 (4)	0.5153 (3)	0.0409 (10)
C42	0.9944 (6)	0.0011 (4)	0.4392 (3)	0.0372 (10)
H42	1.0547	−0.0028	0.3840	0.045*
C43	0.8846 (8)	0.1146 (4)	0.4642 (3)	0.0446 (12)
H43A	0.8015	0.1089	0.5092	0.053*
H43B	0.9736	0.1803	0.4923	0.053*
C45	0.8862 (12)	0.1732 (7)	0.3202 (5)	0.086 (2)
H45A	0.8071	0.1836	0.2697	0.129*
H45B	0.9694	0.1108	0.2990	0.129*
H45C	0.9586	0.2449	0.3500	0.129*
C44	0.7669 (8)	0.1424 (5)	0.3856 (4)	0.0567 (13)
H44	0.6904	0.0713	0.3525	0.068*
C46	0.6333 (10)	0.2383 (6)	0.4227 (5)	0.082 (2)
H46A	0.7042	0.3085	0.4575	0.123*
H46B	0.5531	0.2127	0.4607	0.123*
H46C	0.5579	0.2545	0.3733	0.123*
N41	0.8670 (6)	−0.1047 (4)	0.4223 (3)	0.0399 (9)
H41A	0.9346	−0.1667	0.4233	0.060*
H41B	0.8016	−0.1180	0.3683	0.060*
H41C	0.7883	−0.0929	0.4652	0.060*
O41A	1.1312 (5)	−0.0613 (3)	0.5647 (2)	0.0483 (9)
O41B	1.2785 (6)	0.0786 (4)	0.5222 (3)	0.0718 (12)
H41D	1.3615	0.0730	0.5608	0.108*
C51	0.6333 (7)	0.6409 (4)	0.4631 (3)	0.0418 (10)
C52	0.5207 (6)	0.6460 (4)	0.5426 (3)	0.0368 (9)
H52	0.6083	0.6518	0.5964	0.044*
C53	0.3900 (7)	0.5363 (4)	0.5256 (3)	0.0438 (11)
H53A	0.2832	0.5420	0.4839	0.053*
H53B	0.4571	0.4677	0.4962	0.053*
C54	0.3170 (9)	0.5167 (5)	0.6097 (4)	0.0586 (14)
H54	0.2761	0.5919	0.6471	0.070*
C55	0.4686 (13)	0.4722 (7)	0.6655 (5)	0.093 (3)
H55A	0.4835	0.3899	0.6377	0.139*
H55B	0.4328	0.4833	0.7257	0.139*
H55C	0.5853	0.5152	0.6685	0.139*
C56	0.1461 (11)	0.4290 (7)	0.5805 (6)	0.095 (2)
H56A	0.0498	0.4603	0.5478	0.142*
H56B	0.0984	0.4162	0.6333	0.142*
H56C	0.1834	0.3556	0.5424	0.142*
N51	0.4088 (6)	0.7542 (3)	0.5598 (3)	0.0417 (9)
H51A	0.4820	0.8154	0.5591	0.063*
H51B	0.3647	0.7679	0.6137	0.063*
H51C	0.3131	0.7438	0.5169	0.063*
O51B	0.7605 (6)	0.5641 (4)	0.4548 (3)	0.0674 (11)
H51D	0.8161	0.5631	0.4104	0.101*
O51A	0.6049 (5)	0.7054 (3)	0.4153 (2)	0.0490 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.048 (3)	0.045 (3)	0.031 (2)	−0.001 (2)	0.001 (2)	0.011 (2)
C2	0.044 (3)	0.050 (3)	0.037 (3)	0.007 (2)	0.009 (2)	0.013 (2)
C3	0.048 (3)	0.057 (3)	0.034 (2)	0.005 (2)	0.010 (2)	0.012 (2)
C4	0.063 (4)	0.050 (3)	0.034 (2)	0.007 (3)	0.006 (2)	0.018 (2)
C5	0.049 (3)	0.049 (3)	0.040 (3)	0.005 (2)	−0.003 (2)	0.017 (2)
C6	0.037 (3)	0.048 (3)	0.040 (3)	0.003 (2)	0.007 (2)	0.013 (2)
N3	0.052 (3)	0.073 (3)	0.055 (3)	0.021 (2)	0.013 (2)	0.025 (2)
N1	0.046 (3)	0.075 (3)	0.055 (3)	0.010 (2)	0.008 (2)	0.021 (2)
N2	0.087 (4)	0.067 (3)	0.049 (3)	0.007 (3)	0.011 (3)	0.031 (2)
O1	0.054 (2)	0.074 (3)	0.050 (2)	−0.0001 (19)	0.0081 (17)	0.0334 (19)
O7	0.076 (3)	0.144 (5)	0.071 (3)	0.053 (3)	0.017 (2)	0.056 (3)
O6	0.086 (4)	0.103 (4)	0.075 (3)	0.048 (3)	0.028 (3)	0.028 (3)
O5	0.108 (4)	0.105 (4)	0.063 (3)	0.023 (3)	0.044 (3)	0.045 (3)
O4	0.109 (4)	0.139 (5)	0.094 (4)	0.033 (4)	0.014 (3)	0.084 (4)
O3	0.058 (3)	0.123 (4)	0.095 (4)	0.026 (3)	0.015 (3)	0.048 (3)
O2	0.090 (4)	0.202 (7)	0.093 (4)	0.067 (4)	0.052 (3)	0.083 (4)
C11	0.038 (3)	0.047 (3)	0.039 (3)	−0.006 (2)	0.000 (2)	0.011 (2)
C12	0.038 (3)	0.056 (3)	0.040 (3)	0.005 (2)	0.001 (2)	0.011 (2)
C13	0.052 (3)	0.051 (3)	0.043 (3)	0.002 (2)	−0.003 (2)	0.018 (2)
C14	0.049 (3)	0.052 (3)	0.035 (2)	0.005 (2)	0.006 (2)	0.018 (2)
C15	0.049 (3)	0.062 (3)	0.033 (3)	0.007 (3)	0.005 (2)	0.011 (2)
C16	0.045 (3)	0.054 (3)	0.037 (3)	0.008 (2)	−0.003 (2)	0.014 (2)
N11	0.043 (3)	0.084 (4)	0.068 (3)	0.006 (3)	0.012 (2)	0.029 (3)
N12	0.069 (3)	0.074 (3)	0.043 (3)	0.014 (3)	0.011 (2)	0.026 (2)
N13	0.061 (3)	0.068 (3)	0.047 (3)	0.020 (3)	0.004 (2)	0.020 (2)
O11	0.059 (2)	0.072 (2)	0.043 (2)	−0.0063 (19)	−0.0005 (17)	0.0337 (18)
O12	0.093 (4)	0.192 (7)	0.107 (4)	0.057 (4)	0.062 (4)	0.091 (5)
O13	0.070 (3)	0.186 (6)	0.140 (5)	0.060 (4)	0.038 (3)	0.098 (5)
O14	0.098 (4)	0.118 (4)	0.091 (4)	0.038 (3)	0.021 (3)	0.075 (3)
O15	0.097 (4)	0.127 (4)	0.067 (3)	0.032 (3)	0.036 (3)	0.058 (3)
O16	0.086 (4)	0.124 (4)	0.065 (3)	0.058 (3)	0.024 (3)	0.034 (3)
O17	0.089 (3)	0.121 (4)	0.050 (2)	0.047 (3)	0.006 (2)	0.044 (2)
C21	0.040 (2)	0.045 (3)	0.038 (2)	−0.002 (2)	0.0003 (19)	0.015 (2)
C22	0.047 (3)	0.045 (2)	0.029 (2)	0.002 (2)	−0.0008 (19)	0.0134 (18)
C23	0.067 (4)	0.056 (3)	0.045 (3)	−0.011 (3)	−0.010 (3)	0.019 (2)
C24	0.112 (6)	0.065 (4)	0.055 (3)	−0.027 (4)	−0.018 (4)	0.013 (3)
C25	0.198 (9)	0.133 (6)	0.114 (6)	−0.063 (6)	−0.014 (6)	0.021 (5)
C26	0.198 (9)	0.133 (6)	0.114 (6)	−0.063 (6)	−0.014 (6)	0.021 (5)
N21	0.040 (2)	0.059 (3)	0.043 (2)	0.0047 (19)	0.0021 (18)	0.0242 (19)
O21B	0.057 (2)	0.061 (2)	0.075 (3)	0.016 (2)	−0.0179 (19)	0.0057 (19)
O21A	0.053 (2)	0.0459 (19)	0.0355 (17)	−0.0029 (16)	0.0047 (15)	0.0096 (16)
C31	0.045 (3)	0.049 (3)	0.042 (3)	0.013 (2)	0.011 (2)	0.017 (2)
C32	0.041 (2)	0.044 (2)	0.039 (2)	0.005 (2)	0.0077 (19)	0.0144 (19)
C33	0.064 (3)	0.047 (3)	0.048 (3)	0.009 (3)	0.015 (3)	0.016 (2)
C34	0.178 (6)	0.117 (4)	0.082 (3)	0.084 (4)	0.024 (3)	0.014 (3)
C35	0.178 (6)	0.117 (4)	0.082 (3)	0.084 (4)	0.024 (3)	0.014 (3)
C36	0.178 (6)	0.117 (4)	0.082 (3)	0.084 (4)	0.024 (3)	0.014 (3)
N31	0.054 (3)	0.052 (2)	0.040 (2)	0.008 (2)	0.0100 (19)	0.0244 (18)
O31B	0.072 (3)	0.060 (2)	0.081 (3)	−0.017 (2)	0.039 (2)	0.002 (2)
O31A	0.053 (2)	0.0490 (19)	0.0353 (17)	0.0091 (16)	0.0070 (15)	0.0084 (15)
C41	0.037 (2)	0.044 (2)	0.044 (3)	0.007 (2)	0.0079 (19)	0.015 (2)
C42	0.038 (2)	0.046 (2)	0.033 (2)	0.003 (2)	0.0043 (18)	0.0194 (19)
C43	0.052 (3)	0.043 (3)	0.041 (3)	0.003 (2)	0.003 (2)	0.016 (2)
C45	0.110 (6)	0.102 (5)	0.070 (4)	0.041 (5)	0.029 (4)	0.054 (4)
C44	0.065 (3)	0.048 (3)	0.058 (3)	0.014 (2)	−0.002 (3)	0.018 (2)
C46	0.082 (5)	0.072 (4)	0.095 (5)	0.035 (4)	0.012 (4)	0.028 (4)
N41	0.041 (2)	0.043 (2)	0.038 (2)	0.0052 (17)	0.0057 (17)	0.0153 (17)
O41A	0.053 (2)	0.054 (2)	0.0438 (19)	0.0085 (16)	0.0013 (15)	0.0244 (17)
O41B	0.056 (2)	0.083 (3)	0.085 (3)	−0.022 (2)	−0.021 (2)	0.048 (2)
C51	0.044 (3)	0.040 (2)	0.044 (2)	−0.003 (2)	0.005 (2)	0.017 (2)
C52	0.041 (2)	0.037 (2)	0.035 (2)	0.0043 (19)	0.0048 (19)	0.0153 (18)
C53	0.052 (3)	0.038 (3)	0.043 (3)	−0.003 (2)	0.006 (2)	0.013 (2)
C54	0.073 (4)	0.052 (3)	0.055 (3)	−0.005 (3)	0.021 (3)	0.016 (2)
C55	0.134 (7)	0.087 (5)	0.065 (4)	−0.035 (5)	−0.013 (4)	0.042 (4)
C56	0.090 (5)	0.092 (5)	0.108 (6)	−0.033 (4)	0.018 (4)	0.039 (5)
N51	0.046 (2)	0.039 (2)	0.043 (2)	0.0025 (18)	0.0060 (18)	0.0151 (17)
O51B	0.066 (2)	0.074 (3)	0.082 (3)	0.030 (2)	0.041 (2)	0.044 (2)
O51A	0.055 (2)	0.053 (2)	0.046 (2)	0.0016 (17)	0.0050 (16)	0.0260 (17)

Geometric parameters (Å, º) top

C1—O1	1.253 (6)	C32—C33	1.517 (7)
C1—C6	1.442 (7)	C32—H32	0.9800
C1—C2	1.442 (7)	C33—C34	1.503 (10)
C2—C3	1.382 (7)	C33—H33A	0.9700
C2—N3	1.441 (7)	C33—H33B	0.9700
C3—C4	1.382 (8)	C34—C35	1.406 (15)
C3—H3	0.9300	C34—C36	1.522 (12)
C4—C5	1.380 (7)	C34—H34	0.9800
C4—N2	1.443 (7)	C35—H35A	0.9600
C5—C6	1.382 (7)	C35—H35B	0.9600
C5—H5	0.9300	C35—H35C	0.9600
C6—N1	1.441 (7)	C36—H36A	0.9600
N3—O6	1.210 (6)	C36—H36B	0.9600
N3—O7	1.224 (6)	C36—H36C	0.9600
N1—O2	1.218 (7)	N31—H31A	0.8900
N1—O3	1.231 (7)	N31—H31B	0.8900
N2—O5	1.219 (7)	N31—H31C	0.8900
N2—O4	1.228 (7)	C41—O41A	1.223 (6)
C11—O11	1.239 (6)	C41—O41B	1.275 (6)
C11—C16	1.464 (7)	C41—C42	1.524 (6)
C11—C12	1.472 (7)	C42—N41	1.484 (6)
C12—C13	1.355 (7)	C42—C43	1.541 (7)
C12—N11	1.461 (7)	C42—H42	0.9800
C13—C14	1.369 (7)	C43—C44	1.532 (7)
C13—H13	0.9300	C43—H43A	0.9700
C14—C15	1.390 (8)	C43—H43B	0.9700
C14—N12	1.450 (6)	C45—C44	1.493 (9)
C15—C16	1.355 (7)	C45—H45A	0.9600
C15—H15	0.9300	C45—H45B	0.9600
C16—N13	1.456 (7)	C45—H45C	0.9600
N11—O13	1.198 (7)	C44—C46	1.517 (8)
N11—O12	1.199 (7)	C44—H44	0.9800
N12—O14	1.207 (7)	C46—H46A	0.9600
N12—O15	1.222 (7)	C46—H46B	0.9600
N13—O16	1.218 (6)	C46—H46C	0.9600
N13—O17	1.229 (6)	N41—H41A	0.8900
C21—O21A	1.249 (6)	N41—H41B	0.8900
C21—O21B	1.253 (6)	N41—H41C	0.8900
C21—C22	1.525 (6)	O41B—H41D	0.8200
C22—N21	1.493 (6)	C51—O51A	1.212 (6)
C22—C23	1.540 (7)	C51—O51B	1.286 (6)
C22—H22	0.9800	C51—C52	1.516 (6)
C23—C24	1.510 (8)	C52—N51	1.496 (6)
C23—H23A	0.9700	C52—C53	1.534 (6)
C23—H23B	0.9700	C52—H52	0.9800
C24—C26	1.495 (13)	C53—C54	1.518 (7)
C24—C25	1.594 (15)	C53—H53A	0.9700
C24—H24	0.9800	C53—H53B	0.9700
C25—H25A	0.9600	C54—C55	1.518 (10)
C25—H25B	0.9600	C54—C56	1.539 (9)
C25—H25C	0.9600	C54—H54	0.9800
C26—H26A	0.9600	C55—H55A	0.9600
C26—H26B	0.9600	C55—H55B	0.9600
C26—H26C	0.9600	C55—H55C	0.9600
N21—H21A	0.8900	C56—H56A	0.9600
N21—H21B	0.8900	C56—H56B	0.9600
N21—H21C	0.8900	C56—H56C	0.9600
C31—O31A	1.247 (6)	N51—H51A	0.8900
C31—O31B	1.253 (6)	N51—H51B	0.8900
C31—C32	1.532 (6)	N51—H51C	0.8900
C32—N31	1.496 (6)	O51B—H51D	0.8200

O1—C1—C6	124.5 (5)	C32—C33—H33B	108.2
O1—C1—C2	122.5 (5)	H33A—C33—H33B	107.4
C6—C1—C2	113.0 (4)	C35—C34—C33	115.4 (9)
C3—C2—N3	116.9 (5)	C35—C34—C36	109.7 (8)
C3—C2—C1	123.9 (5)	C33—C34—C36	112.0 (7)
N3—C2—C1	119.2 (4)	C35—C34—H34	106.4
C2—C3—C4	118.7 (5)	C33—C34—H34	106.4
C2—C3—H3	120.6	C36—C34—H34	106.4
C4—C3—H3	120.6	C34—C35—H35A	109.5
C5—C4—C3	121.5 (4)	C34—C35—H35B	109.5
C5—C4—N2	119.7 (5)	H35A—C35—H35B	109.5
C3—C4—N2	118.8 (5)	C34—C35—H35C	109.5
C4—C5—C6	119.5 (5)	H35A—C35—H35C	109.5
C4—C5—H5	120.3	H35B—C35—H35C	109.5
C6—C5—H5	120.3	C34—C36—H36A	109.5
C5—C6—N1	116.5 (5)	C34—C36—H36B	109.5
C5—C6—C1	123.3 (4)	H36A—C36—H36B	109.5
N1—C6—C1	120.2 (4)	C34—C36—H36C	109.5
O6—N3—O7	121.4 (5)	H36A—C36—H36C	109.5
O6—N3—C2	118.7 (5)	H36B—C36—H36C	109.5
O7—N3—C2	119.9 (5)	C32—N31—H31A	109.5
O2—N1—O3	120.4 (5)	C32—N31—H31B	109.5
O2—N1—C6	119.7 (5)	H31A—N31—H31B	109.5
O3—N1—C6	119.9 (5)	C32—N31—H31C	109.5
O5—N2—O4	123.2 (5)	H31A—N31—H31C	109.5
O5—N2—C4	118.6 (5)	H31B—N31—H31C	109.5
O4—N2—C4	118.1 (5)	O41A—C41—O41B	126.4 (5)
O11—C11—C16	124.6 (5)	O41A—C41—C42	121.5 (4)
O11—C11—C12	125.1 (5)	O41B—C41—C42	112.1 (4)
C16—C11—C12	110.3 (4)	N41—C42—C41	109.2 (3)
C13—C12—N11	117.4 (5)	N41—C42—C43	111.0 (4)
C13—C12—C11	123.9 (5)	C41—C42—C43	110.2 (4)
N11—C12—C11	118.6 (5)	N41—C42—H42	108.8
C12—C13—C14	120.6 (5)	C41—C42—H42	108.8
C12—C13—H13	119.7	C43—C42—H42	108.8
C14—C13—H13	119.7	C44—C43—C42	115.8 (4)
C13—C14—C15	120.8 (5)	C44—C43—H43A	108.3
C13—C14—N12	120.2 (5)	C42—C43—H43A	108.3
C15—C14—N12	118.9 (5)	C44—C43—H43B	108.3
C16—C15—C14	119.0 (5)	C42—C43—H43B	108.3
C16—C15—H15	120.5	H43A—C43—H43B	107.4
C14—C15—H15	120.5	C44—C45—H45A	109.5
C15—C16—N13	116.5 (5)	C44—C45—H45B	109.5
C15—C16—C11	125.3 (5)	H45A—C45—H45B	109.5
N13—C16—C11	118.2 (4)	C44—C45—H45C	109.5
O13—N11—O12	121.8 (6)	H45A—C45—H45C	109.5
O13—N11—C12	117.4 (5)	H45B—C45—H45C	109.5
O12—N11—C12	120.7 (5)	C45—C44—C46	112.2 (5)
O14—N12—O15	122.4 (5)	C45—C44—C43	112.3 (5)
O14—N12—C14	118.8 (5)	C46—C44—C43	109.6 (5)
O15—N12—C14	118.8 (5)	C45—C44—H44	107.5
O16—N13—O17	122.8 (5)	C46—C44—H44	107.5
O16—N13—C16	119.2 (5)	C43—C44—H44	107.5
O17—N13—C16	118.0 (5)	C44—C46—H46A	109.5
O21A—C21—O21B	126.4 (4)	C44—C46—H46B	109.5
O21A—C21—C22	119.3 (4)	H46A—C46—H46B	109.5
O21B—C21—C22	114.2 (4)	C44—C46—H46C	109.5
N21—C22—C21	108.7 (4)	H46A—C46—H46C	109.5
N21—C22—C23	110.3 (4)	H46B—C46—H46C	109.5
C21—C22—C23	112.3 (4)	C42—N41—H41A	109.5
N21—C22—H22	108.5	C42—N41—H41B	109.5
C21—C22—H22	108.5	H41A—N41—H41B	109.5
C23—C22—H22	108.5	C42—N41—H41C	109.5
C24—C23—C22	114.6 (5)	H41A—N41—H41C	109.5
C24—C23—H23A	108.6	H41B—N41—H41C	109.5
C22—C23—H23A	108.6	C41—O41B—H41D	109.5
C24—C23—H23B	108.6	O51A—C51—O51B	125.5 (4)
C22—C23—H23B	108.6	O51A—C51—C52	121.8 (4)
H23A—C23—H23B	107.6	O51B—C51—C52	112.7 (4)
C26—C24—C23	113.7 (7)	N51—C52—C51	108.7 (3)
C26—C24—C25	106.7 (8)	N51—C52—C53	110.2 (4)
C23—C24—C25	106.6 (7)	C51—C52—C53	112.1 (4)
C26—C24—H24	109.9	N51—C52—H52	108.6
C23—C24—H24	109.9	C51—C52—H52	108.6
C25—C24—H24	109.9	C53—C52—H52	108.6
C24—C25—H25A	109.5	C54—C53—C52	115.2 (4)
C24—C25—H25B	109.5	C54—C53—H53A	108.5
H25A—C25—H25B	109.5	C52—C53—H53A	108.5
C24—C25—H25C	109.5	C54—C53—H53B	108.5
H25A—C25—H25C	109.5	C52—C53—H53B	108.5
H25B—C25—H25C	109.5	H53A—C53—H53B	107.5
C24—C26—H26A	109.5	C53—C54—C55	111.4 (5)
C24—C26—H26B	109.5	C53—C54—C56	108.8 (5)
H26A—C26—H26B	109.5	C55—C54—C56	110.8 (5)
C24—C26—H26C	109.5	C53—C54—H54	108.6
H26A—C26—H26C	109.5	C55—C54—H54	108.6
H26B—C26—H26C	109.5	C56—C54—H54	108.6
C22—N21—H21A	109.5	C54—C55—H55A	109.5
C22—N21—H21B	109.5	C54—C55—H55B	109.5
H21A—N21—H21B	109.5	H55A—C55—H55B	109.5
C22—N21—H21C	109.5	C54—C55—H55C	109.5
H21A—N21—H21C	109.5	H55A—C55—H55C	109.5
H21B—N21—H21C	109.5	H55B—C55—H55C	109.5
O31A—C31—O31B	126.4 (4)	C54—C56—H56A	109.5
O31A—C31—C32	119.8 (4)	C54—C56—H56B	109.5
O31B—C31—C32	113.7 (4)	H56A—C56—H56B	109.5
N31—C32—C33	110.3 (4)	C54—C56—H56C	109.5
N31—C32—C31	108.6 (4)	H56A—C56—H56C	109.5
C33—C32—C31	112.3 (4)	H56B—C56—H56C	109.5
N31—C32—H32	108.5	C52—N51—H51A	109.5
C33—C32—H32	108.5	C52—N51—H51B	109.5
C31—C32—H32	108.5	H51A—N51—H51B	109.5
C34—C33—C32	116.2 (5)	C52—N51—H51C	109.5
C34—C33—H33A	108.2	H51A—N51—H51C	109.5
C32—C33—H33A	108.2	H51B—N51—H51C	109.5
C34—C33—H33B	108.2	C51—O51B—H51D	109.5

O1—C1—C2—C3	−176.1 (5)	C11—C12—N11—O13	−171.7 (6)
C6—C1—C2—C3	1.5 (7)	C13—C12—N11—O12	−173.6 (6)
O1—C1—C2—N3	4.6 (7)	C11—C12—N11—O12	5.3 (9)
C6—C1—C2—N3	−177.8 (5)	C13—C14—N12—O14	−1.6 (9)
N3—C2—C3—C4	179.6 (5)	C15—C14—N12—O14	175.4 (6)
C1—C2—C3—C4	0.3 (8)	C13—C14—N12—O15	179.3 (6)
C2—C3—C4—C5	−1.3 (8)	C15—C14—N12—O15	−3.6 (8)
C2—C3—C4—N2	177.7 (5)	C15—C16—N13—O16	−23.1 (8)
C3—C4—C5—C6	0.3 (8)	C11—C16—N13—O16	154.3 (6)
N2—C4—C5—C6	−178.6 (5)	C15—C16—N13—O17	153.3 (6)
C4—C5—C6—N1	−177.1 (5)	C11—C16—N13—O17	−29.3 (8)
C4—C5—C6—C1	1.7 (7)	O21A—C21—C22—N21	−9.5 (6)
O1—C1—C6—C5	175.0 (5)	O21B—C21—C22—N21	170.4 (4)
C2—C1—C6—C5	−2.5 (7)	O21A—C21—C22—C23	112.8 (5)
O1—C1—C6—N1	−6.2 (7)	O21B—C21—C22—C23	−67.3 (6)
C2—C1—C6—N1	176.3 (4)	N21—C22—C23—C24	−78.6 (6)
C3—C2—N3—O6	28.3 (8)	C21—C22—C23—C24	160.0 (5)
C1—C2—N3—O6	−152.3 (5)	C22—C23—C24—C26	163.5 (8)
C3—C2—N3—O7	−151.8 (6)	C22—C23—C24—C25	−79.2 (7)
C1—C2—N3—O7	27.5 (8)	O31A—C31—C32—N31	−9.5 (6)
C5—C6—N1—O2	166.1 (6)	O31B—C31—C32—N31	172.3 (4)
C1—C6—N1—O2	−12.8 (8)	O31A—C31—C32—C33	112.7 (5)
C5—C6—N1—O3	−14.2 (8)	O31B—C31—C32—C33	−65.5 (6)
C1—C6—N1—O3	166.9 (5)	N31—C32—C33—C34	−71.0 (8)
C5—C4—N2—O5	177.6 (5)	C31—C32—C33—C34	167.8 (7)
C3—C4—N2—O5	−1.3 (8)	C32—C33—C34—C35	−69.7 (11)
C5—C4—N2—O4	2.2 (9)	C32—C33—C34—C36	163.9 (8)
C3—C4—N2—O4	−176.8 (6)	O41A—C41—C42—N41	−14.8 (6)
O11—C11—C12—C13	−177.3 (5)	O41B—C41—C42—N41	168.3 (4)
C16—C11—C12—C13	1.3 (7)	O41A—C41—C42—C43	107.4 (5)
O11—C11—C12—N11	4.0 (8)	O41B—C41—C42—C43	−69.5 (5)
C16—C11—C12—N11	−177.5 (5)	N41—C42—C43—C44	−75.3 (5)
N11—C12—C13—C14	177.1 (5)	C41—C42—C43—C44	163.6 (4)
C11—C12—C13—C14	−1.7 (8)	C42—C43—C44—C45	−67.9 (6)
C12—C13—C14—C15	2.5 (8)	C42—C43—C44—C46	166.7 (5)
C12—C13—C14—N12	179.5 (5)	O51A—C51—C52—N51	−11.3 (6)
C13—C14—C15—C16	−2.9 (8)	O51B—C51—C52—N51	167.2 (4)
N12—C14—C15—C16	−179.9 (5)	O51A—C51—C52—C53	110.7 (5)
C14—C15—C16—N13	179.9 (5)	O51B—C51—C52—C53	−70.8 (5)
C14—C15—C16—C11	2.7 (8)	N51—C52—C53—C54	−76.2 (5)
O11—C11—C16—C15	176.7 (5)	C51—C52—C53—C54	162.6 (5)
C12—C11—C16—C15	−1.8 (7)	C52—C53—C54—C55	−74.6 (6)
O11—C11—C16—N13	−0.4 (7)	C52—C53—C54—C56	162.9 (5)
C12—C11—C16—N13	−179.0 (4)	H41D—O21Bⁱ—C21ⁱ—O21Aⁱ	2.5
C13—C12—N11—O13	9.4 (9)	H51D—O31Bⁱ—C31ⁱ—O31Aⁱ	2.4

Symmetry code: (i) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O51B—H51D···O31Bⁱ	0.82	1.65	2.454 (5)	166
N51—H51C···O31A	0.89	2.12	2.999 (5)	168
N51—H51B···O7	0.89	2.23	3.098 (6)	164
N51—H51A···O21Aⁱⁱ	0.89	1.93	2.798 (5)	166
O41B—H41D···O21Bⁱ	0.82	1.68	2.471 (5)	161
N41—H41C···O21A	0.89	2.07	2.942 (5)	166
N41—H41B···O11ⁱⁱⁱ	0.89	2.02	2.907 (5)	173
N41—H41A···O31A^iv	0.89	2.05	2.913 (5)	162
N31—H31C···O5^v	0.89	2.16	2.977 (6)	153
N31—H31B···O17^vi	0.89	2.25	2.998 (6)	142
N31—H31B···O12	0.89	2.62	3.364 (9)	142
N31—H31A···O51A	0.89	1.97	2.861 (5)	176
N21—H21C···O41A	0.89	2.10	2.983 (5)	174
N21—H21B···O6^iv	0.89	2.57	3.355 (6)	147
N21—H21B···O15^vii	0.89	2.56	3.084 (6)	118
N21—H21A···O1ⁱⁱⁱ	0.89	1.91	2.753 (6)	157

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

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