Mixed 3,5-dinitro­salicylate(2–) and partial 3,5-dinitro­salicylate(1–) and picrate(1–) species in tris(piperidinium) bis(3,5-dinitro­salicylate) picrate monohydrate

The crystal structure of the monohydrated proton-transfer compound of 3,5-dinitro­salicylic acid with piperidine shows the presence of dianionic 3,5-dinitro­salicylate species, as well as partial monoanionic 3,5-dinitro­salicylate and picrate species; the formula is 3C₅H₁₂N⁺·C₇H₃N₂O₇⁻·0.79C₇H₂N₂O₇²⁻·0.21C₆H₂N₃O₇⁻·H₂O. All available proton-donor species, including the solvent water mol­ecule, are involved in hydrogen-bonding inter­actions with O-atom acceptors on the anion species, giving a one-dimensional column polymer structure, with further structure extension through anion–anion π–π ring inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.055
• wR factor = 0.211
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       O71A
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       O72A
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       N71A
PLAT417_ALERT_2_B Short Inter D-H..H-D       H11D   ..  H21A    ..       1.90 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.62 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N5A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C6A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N3B
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C5E
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N1E
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.30
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1W    ..  H12D    ..       2.13 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

tris(piperidinium) bis(3,5-dinitrosalicylate) picrate monohydrate

Crystal data

3C5H12N^+·C7H2N2O7^2^−·0.79C7H3N2O7^−·0.21C6H2N3O7^−·H2O	Z = 2
Mr = 729.91	F(000) = 772
Triclinic, P1	Dx = 1.388 Mg m^−3
Hall symbol: -P 1	Melting point = 419–424 K
a = 12.5457 (15) Å	Mo Kα radiation, λ = 0.71069 Å
b = 12.903 (2) Å	Cell parameters from 17 reflections
c = 13.1415 (17) Å	θ = 10.1–16.3°
α = 67.63 (1)°	µ = 0.11 mm^−1
β = 89.012 (10)°	T = 297 K
γ = 64.41 (1)°	Block, yellow
V = 1746.4 (5) Å^3	0.30 × 0.25 × 0.20 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.026
Radiation source: Rigaku rotating anode	θmax = 25.0°, θmin = 2.7°
Graphite monochromator	h = −14→7
ω/2θ scans	k = −15→13
7072 measured reflections	l = −15→15
6147 independent reflections	3 standard reflections every 150 min
2203 reflections with I > 2σ(I)	intensity decay: 2.4%

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) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.2218P] where P = (Fo^2 + 2Fc^2)/3
6147 reflections	(Δ/σ)max = 0.003
507 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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)
O2A	−0.1884 (5)	0.5529 (6)	0.6300 (4)	0.090 (3)	0.790
O31A	−0.2883 (4)	0.7894 (5)	0.5406 (5)	0.132 (3)
O32A	−0.1796 (4)	0.8911 (4)	0.4904 (4)	0.1071 (19)
O51A	0.2396 (3)	0.6678 (4)	0.5172 (4)	0.1000 (19)
O52A	0.3374 (4)	0.4667 (4)	0.5992 (4)	0.112 (2)
O71A	0.1221 (5)	0.2231 (4)	0.7150 (3)	0.097 (2)
O72A	−0.0671 (5)	0.3096 (4)	0.7129 (3)	0.103 (2)
N3A	−0.1901 (5)	0.7939 (6)	0.5297 (5)	0.094 (3)
N5A	0.2432 (4)	0.5653 (5)	0.5667 (4)	0.0644 (17)
C1A	0.0226 (5)	0.4408 (4)	0.6474 (3)	0.0506 (19)
C2A	−0.0871 (4)	0.5525 (5)	0.6169 (4)	0.0556 (19)
C3A	−0.0797 (4)	0.6681 (5)	0.5688 (4)	0.0525 (17)
C4A	0.0284 (4)	0.6692 (4)	0.5560 (4)	0.0475 (17)
C5A	0.1325 (4)	0.5580 (4)	0.5863 (4)	0.0432 (17)
C6A	0.1322 (4)	0.4429 (5)	0.6316 (4)	0.0469 (17)
C7A	0.0240 (10)	0.3201 (9)	0.6937 (6)	0.077 (8)	0.790
O6A	0.2129 (16)	0.3350 (18)	0.6628 (17)	0.100 (8)	0.210
N71A	0.0240 (10)	0.3201 (9)	0.6937 (6)	0.040 (8)*	0.210
O2B	0.3490 (3)	0.1493 (3)	0.9673 (3)	0.0683 (14)
O31B	0.4369 (4)	0.3113 (4)	0.9037 (5)	0.107 (3)
O32B	0.3278 (4)	0.4968 (4)	0.8746 (5)	0.104 (3)
O51B	−0.0958 (3)	0.6781 (3)	0.8162 (3)	0.0686 (14)
O52B	−0.1818 (3)	0.5579 (3)	0.8696 (3)	0.0746 (16)
O71B	0.0336 (3)	0.1132 (3)	0.9973 (3)	0.0580 (12)
O72B	0.2285 (3)	0.0120 (3)	1.0578 (3)	0.0747 (14)
N3B	0.3390 (4)	0.3946 (4)	0.8931 (4)	0.0628 (17)
N5B	−0.0916 (4)	0.5736 (4)	0.8557 (3)	0.0504 (16)
C1B	0.1367 (4)	0.2364 (4)	0.9617 (3)	0.0384 (17)
C2B	0.2495 (4)	0.2442 (4)	0.9469 (3)	0.0399 (17)
C3B	0.2350 (4)	0.3717 (4)	0.9054 (4)	0.0429 (17)
C4B	0.1265 (4)	0.4763 (4)	0.8792 (3)	0.0422 (17)
C5B	0.0238 (4)	0.4626 (4)	0.8894 (3)	0.0396 (17)
C6B	0.0301 (3)	0.3438 (4)	0.9321 (3)	0.0385 (17)
C7B	0.1351 (4)	0.1108 (4)	1.0088 (4)	0.0429 (17)
N1C	0.0382 (4)	1.0126 (5)	0.8119 (4)	0.0595 (19)
C2C	−0.0391 (5)	1.0438 (5)	0.7101 (5)	0.074 (2)
C3C	−0.0264 (6)	0.9261 (6)	0.7049 (5)	0.089 (3)
C4C	0.1031 (7)	0.8371 (6)	0.7107 (6)	0.094 (3)
C5C	0.1789 (5)	0.8098 (6)	0.8151 (6)	0.088 (3)
C6C	0.1662 (5)	0.9288 (5)	0.8181 (5)	0.073 (2)
N1D	0.6738 (4)	0.4471 (5)	0.7732 (4)	0.0663 (19)
C2D	0.6051 (5)	0.5042 (6)	0.8472 (5)	0.074 (2)
C3D	0.5345 (5)	0.6441 (6)	0.7835 (6)	0.096 (3)
C4D	0.4540 (5)	0.6790 (5)	0.6785 (6)	0.093 (3)
C5D	0.5233 (5)	0.6144 (5)	0.6077 (5)	0.083 (2)
C6D	0.5935 (5)	0.4752 (5)	0.6740 (5)	0.074 (2)
N1E	0.5268 (4)	0.0740 (4)	0.8428 (4)	0.0603 (17)
C2E	0.5523 (5)	0.1632 (5)	0.7488 (5)	0.081 (2)
C3E	0.6290 (6)	0.0976 (8)	0.6824 (6)	0.120 (3)
C4E	0.5711 (8)	0.0416 (9)	0.6389 (8)	0.137 (4)
C5E	0.5424 (8)	−0.0484 (7)	0.7334 (9)	0.138 (4)
C6E	0.4663 (6)	0.0173 (6)	0.8035 (6)	0.104 (3)
O1W	0.8013 (4)	0.1952 (4)	0.8937 (4)	0.0755 (16)
H21A	−0.146 (4)	0.462 (4)	0.661 (4)	0.016 (13)*	0.790
H4A	0.031200	0.747300	0.526200	0.0580*
H6A	0.206500	0.364900	0.652000	0.0490*	0.790
H2A	−0.161600	0.551000	0.627000	0.0490*	0.210
H4B	0.122100	0.557600	0.854200	0.0500*
H6B	−0.042100	0.336700	0.941000	0.0460*
H11C	0.029 (4)	1.089 (4)	0.814 (4)	0.056 (17)*
H12C	0.011 (5)	0.972 (6)	0.876 (5)	0.12 (2)*
H21C	−0.120500	1.094200	0.711800	0.0890*
H22C	−0.015900	1.089100	0.645900	0.0890*
H31C	−0.056300	0.885100	0.765800	0.1060*
H32C	−0.072200	0.947800	0.636500	0.1060*
H41C	0.108400	0.760600	0.713000	0.1130*
H42C	0.131500	0.875000	0.646500	0.1130*
H51C	0.153700	0.766800	0.879000	0.1040*
H52C	0.260700	0.758300	0.815900	0.1040*
H61C	0.195000	0.970200	0.756200	0.0870*
H62C	0.211600	0.909500	0.885600	0.0870*
H11D	0.727 (5)	0.481 (5)	0.744 (4)	0.094 (19)*
H12D	0.713 (6)	0.357 (7)	0.820 (6)	0.13 (2)*
H21D	0.551800	0.469600	0.874500	0.0890*
H22D	0.659200	0.486400	0.908300	0.0890*
H31D	0.486000	0.678500	0.829800	0.1150*
H32D	0.588600	0.679000	0.762400	0.1150*
H41D	0.392600	0.654600	0.699500	0.1120*
H42D	0.418500	0.767800	0.636200	0.1120*
H51D	0.468500	0.630400	0.548200	0.0990*
H52D	0.576900	0.647800	0.578400	0.0990*
H61D	0.640900	0.438400	0.628100	0.0880*
H62D	0.539800	0.440400	0.698200	0.0880*
H62E	0.39040	0.081600	0.75900	0.1250*
H11E	0.600 (6)	0.009 (6)	0.895 (5)	0.14 (2)*
H12E	0.480 (4)	0.105 (5)	0.885 (4)	0.059 (19)*
H21E	0.478700	0.230200	0.701700	0.0970*
H22E	0.592900	0.196600	0.777000	0.0970*
H31E	0.642900	0.157000	0.621400	0.1440*
H32E	0.703200	0.032700	0.729000	0.1440*
H41E	0.498500	0.107500	0.588900	0.1640*
H42E	0.623200	−0.001900	0.600000	0.1640*
H51E	0.499100	−0.078100	0.702900	0.1650*
H52E	0.615200	−0.117400	0.779200	0.1650*
H61E	0.455200	−0.042800	0.865900	0.1250*
H1W	0.868 (6)	0.183 (5)	0.911 (5)	0.10 (2)*
H2W	0.795 (5)	0.128 (6)	0.912 (5)	0.12 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2A	0.074 (4)	0.130 (5)	0.096 (4)	−0.072 (4)	0.036 (3)	−0.048 (4)
O31A	0.044 (3)	0.134 (4)	0.216 (6)	−0.034 (3)	0.031 (3)	−0.080 (4)
O32A	0.092 (3)	0.073 (3)	0.141 (4)	−0.025 (3)	0.015 (3)	−0.044 (3)
O51A	0.082 (3)	0.101 (3)	0.121 (4)	−0.068 (3)	0.026 (2)	−0.020 (3)
O52A	0.045 (2)	0.109 (4)	0.155 (4)	−0.028 (3)	0.015 (3)	−0.038 (3)
O71A	0.165 (5)	0.069 (3)	0.069 (3)	−0.069 (3)	0.012 (3)	−0.022 (2)
O72A	0.155 (5)	0.122 (4)	0.081 (3)	−0.114 (4)	0.032 (3)	−0.032 (3)
N3A	0.068 (4)	0.108 (5)	0.110 (4)	−0.025 (4)	0.018 (3)	−0.066 (4)
N5A	0.048 (3)	0.082 (3)	0.065 (3)	−0.036 (3)	0.011 (2)	−0.025 (3)
C1A	0.078 (4)	0.057 (3)	0.031 (3)	−0.046 (3)	0.014 (2)	−0.015 (2)
C2A	0.056 (3)	0.092 (4)	0.043 (3)	−0.048 (3)	0.024 (3)	−0.036 (3)
C3A	0.050 (3)	0.064 (3)	0.053 (3)	−0.026 (3)	0.014 (2)	−0.034 (3)
C4A	0.056 (3)	0.049 (3)	0.047 (3)	−0.033 (3)	0.012 (2)	−0.019 (2)
C5A	0.039 (3)	0.054 (3)	0.043 (3)	−0.027 (2)	0.011 (2)	−0.020 (2)
C6A	0.055 (3)	0.049 (3)	0.037 (3)	−0.023 (3)	0.006 (2)	−0.019 (2)
C7A	0.15 (2)	0.073 (11)	0.038 (8)	−0.078 (12)	0.018 (6)	−0.022 (5)
O6A	0.064 (12)	0.073 (13)	0.126 (18)	−0.014 (11)	0.019 (11)	−0.026 (12)
O2B	0.042 (2)	0.046 (2)	0.093 (3)	−0.0174 (17)	0.0218 (18)	−0.0091 (19)
O31B	0.056 (3)	0.089 (3)	0.190 (7)	−0.045 (3)	0.053 (3)	−0.087 (4)
O32B	0.081 (3)	0.068 (3)	0.174 (7)	−0.059 (3)	0.055 (3)	−0.060 (3)
O51B	0.069 (2)	0.045 (2)	0.073 (3)	−0.0129 (19)	0.0070 (19)	−0.0213 (19)
O52B	0.039 (2)	0.074 (3)	0.098 (3)	−0.0180 (19)	0.0067 (19)	−0.032 (2)
O71B	0.051 (2)	0.053 (2)	0.071 (2)	−0.0352 (16)	0.0074 (17)	−0.0135 (17)
O72B	0.052 (2)	0.042 (2)	0.104 (3)	−0.0213 (18)	−0.006 (2)	−0.0042 (19)
N3B	0.051 (3)	0.055 (3)	0.094 (3)	−0.036 (2)	0.021 (2)	−0.029 (3)
N5B	0.051 (3)	0.044 (3)	0.045 (2)	−0.011 (2)	0.004 (2)	−0.020 (2)
C1B	0.038 (3)	0.042 (3)	0.035 (3)	−0.020 (2)	0.006 (2)	−0.014 (2)
C2B	0.034 (3)	0.039 (3)	0.040 (3)	−0.015 (2)	0.008 (2)	−0.012 (2)
C3B	0.042 (3)	0.049 (3)	0.050 (3)	−0.027 (2)	0.017 (2)	−0.026 (2)
C4B	0.055 (3)	0.041 (3)	0.037 (3)	−0.027 (2)	0.015 (2)	−0.017 (2)
C5B	0.038 (3)	0.037 (3)	0.042 (3)	−0.015 (2)	0.003 (2)	−0.017 (2)
C6B	0.035 (3)	0.051 (3)	0.034 (3)	−0.025 (2)	0.007 (2)	−0.016 (2)
C7B	0.046 (3)	0.041 (3)	0.046 (3)	−0.027 (2)	0.005 (2)	−0.014 (2)
N1C	0.068 (3)	0.048 (3)	0.071 (4)	−0.032 (3)	0.018 (3)	−0.027 (3)
C2C	0.075 (4)	0.065 (4)	0.070 (4)	−0.031 (3)	0.001 (3)	−0.016 (3)
C3C	0.105 (5)	0.095 (5)	0.084 (4)	−0.057 (4)	0.009 (4)	−0.041 (4)
C4C	0.125 (6)	0.081 (4)	0.100 (5)	−0.053 (4)	0.040 (5)	−0.055 (4)
C5C	0.073 (4)	0.077 (4)	0.102 (5)	−0.021 (3)	0.030 (4)	−0.042 (4)
C6C	0.055 (3)	0.086 (4)	0.084 (4)	−0.037 (3)	0.023 (3)	−0.037 (3)
N1D	0.045 (3)	0.052 (3)	0.087 (4)	−0.025 (2)	0.012 (3)	−0.011 (3)
C2D	0.054 (3)	0.083 (4)	0.089 (4)	−0.037 (3)	0.014 (3)	−0.033 (4)
C3D	0.053 (4)	0.083 (5)	0.162 (7)	−0.027 (3)	0.015 (4)	−0.066 (5)
C4D	0.051 (3)	0.067 (4)	0.134 (6)	−0.019 (3)	0.009 (4)	−0.023 (4)
C5D	0.052 (3)	0.074 (4)	0.091 (4)	−0.027 (3)	0.000 (3)	−0.004 (4)
C6D	0.059 (3)	0.076 (4)	0.077 (4)	−0.033 (3)	0.012 (3)	−0.020 (3)
N1E	0.050 (3)	0.055 (3)	0.072 (3)	−0.023 (2)	0.013 (3)	−0.024 (3)
C2E	0.072 (4)	0.060 (4)	0.082 (4)	−0.030 (3)	−0.005 (3)	−0.001 (3)
C3E	0.083 (5)	0.145 (7)	0.080 (5)	−0.039 (5)	0.025 (4)	−0.013 (5)
C4E	0.127 (7)	0.128 (8)	0.130 (8)	−0.015 (6)	0.009 (6)	−0.078 (7)
C5E	0.151 (8)	0.077 (5)	0.169 (9)	−0.022 (5)	−0.035 (7)	−0.068 (6)
C6E	0.098 (5)	0.089 (5)	0.124 (6)	−0.060 (4)	−0.003 (4)	−0.022 (4)
O1W	0.058 (3)	0.047 (2)	0.102 (3)	−0.025 (2)	−0.005 (2)	−0.010 (2)

Geometric parameters (Å, º)

O2A—C2A	1.278 (9)	C1B—C6B	1.366 (7)
O6A—C6A	1.22 (2)	C2B—C3B	1.449 (7)
O31A—N3A	1.261 (9)	C3B—C4B	1.367 (7)
O32A—N3A	1.227 (9)	C4B—C5B	1.372 (8)
O51A—N5A	1.212 (8)	C5B—C6B	1.383 (7)
O52A—N5A	1.226 (8)	C4B—H4B	0.9485
O71A—N71A	1.255 (13)	C6B—H6B	0.9500
O71A—C7A	1.255 (13)	C2C—C3C	1.485 (10)
O72A—C7A	1.219 (15)	C3C—C4C	1.513 (12)
O72A—N71A	1.2091	C4C—C5C	1.516 (11)
O2A—H21A	0.96 (5)	C5C—C6C	1.490 (10)
O2B—C2B	1.253 (6)	C2C—H22C	0.9494
O31B—N3B	1.198 (8)	C2C—H21C	0.9502
O32B—N3B	1.189 (8)	C3C—H31C	0.9487
O51B—N5B	1.224 (6)	C3C—H32C	0.9507
O52B—N5B	1.232 (7)	C4C—H41C	0.9489
O71B—C7B	1.271 (7)	C4C—H42C	0.9508
O72B—C7B	1.234 (6)	C5C—H52C	0.9491
N3A—C3A	1.505 (9)	C5C—H51C	0.9491
N5A—C5A	1.444 (8)	C6C—H62C	0.9487
N71A—C1A	1.432 (12)	C6C—H61C	0.9505
O1W—H2W	0.85 (7)	C2D—C3D	1.496 (10)
O1W—H1W	0.80 (8)	C3D—C4D	1.520 (10)
N3B—C3B	1.451 (8)	C4D—C5D	1.501 (9)
N5B—C5B	1.446 (7)	C5D—C6D	1.493 (9)
N1C—C6C	1.481 (9)	C2D—H21D	0.9502
N1C—C2C	1.480 (8)	C2D—H22D	0.9497
N1C—H11C	0.95 (5)	C3D—H31D	0.9471
N1C—H12C	0.95 (6)	C3D—H32D	0.9502
N1D—C6D	1.489 (8)	C4D—H42D	0.9503
N1D—C2D	1.483 (9)	C4D—H41D	0.9512
N1D—H12D	0.97 (8)	C5D—H51D	0.9486
N1D—H11D	0.95 (7)	C5D—H52D	0.9494
N1E—C6E	1.469 (10)	C6D—H62D	0.9497
N1E—C2E	1.475 (8)	C6D—H61D	0.9511
N1E—H12E	0.88 (6)	C2E—C3E	1.494 (11)
N1E—H11E	0.97 (7)	C3E—C4E	1.469 (14)
C1A—C6A	1.397 (9)	C4E—C5E	1.506 (15)
C1A—C2A	1.413 (8)	C5E—C6E	1.531 (13)
C1A—C7A	1.432 (12)	C2E—H22E	0.9488
C2A—C3A	1.426 (8)	C2E—H21E	0.9518
C3A—C4A	1.369 (8)	C3E—H31E	0.9505
C4A—C5A	1.374 (7)	C3E—H32E	0.9480
C5A—C6A	1.375 (8)	C4E—H42E	0.9453
C2A—H2A	0.9492	C4E—H41E	0.9543
C4A—H4A	0.9486	C5E—H51E	0.9523
C6A—H6A	0.9729	C5E—H52E	0.9475
C1B—C7B	1.508 (7)	C6E—H61E	0.9479
C1B—C2B	1.466 (8)	C6E—H62E	0.9511
C2A—O2A—H21A	88 (3)	N1C—C6C—C5C	109.6 (6)
O31A—N3A—C3A	115.5 (6)	N1C—C2C—H21C	109.43
O32A—N3A—C3A	119.5 (6)	C3C—C2C—H21C	109.27
O31A—N3A—O32A	125.1 (7)	C3C—C2C—H22C	109.24
O51A—N5A—O52A	122.5 (6)	H21C—C2C—H22C	109.49
O51A—N5A—C5A	119.1 (5)	N1C—C2C—H22C	109.46
O52A—N5A—C5A	118.4 (5)	C4C—C3C—H32C	108.94
O71A—N71A—C1A	117.8 (10)	H31C—C3C—H32C	109.56
O72A—N71A—C1A	121.8 (9)	C2C—C3C—H32C	108.64
O71A—N71A—O72A	119.6 (10)	C4C—C3C—H31C	109.08
H1W—O1W—H2W	113 (7)	C2C—C3C—H31C	108.73
O31B—N3B—O32B	119.2 (6)	C5C—C4C—H41C	109.51
O31B—N3B—C3B	121.0 (5)	H41C—C4C—H42C	109.46
O32B—N3B—C3B	119.8 (5)	C3C—C4C—H42C	109.45
O52B—N5B—C5B	117.8 (4)	C5C—C4C—H42C	109.51
O51B—N5B—O52B	122.9 (5)	C3C—C4C—H41C	109.42
O51B—N5B—C5B	119.3 (5)	H51C—C5C—H52C	109.58
C2C—N1C—C6C	112.7 (5)	C4C—C5C—H52C	109.12
C2C—N1C—H12C	113 (4)	C4C—C5C—H51C	109.12
C2C—N1C—H11C	108 (4)	C6C—C5C—H51C	108.99
H11C—N1C—H12C	107 (5)	C6C—C5C—H52C	109.00
C6C—N1C—H12C	111 (4)	N1C—C6C—H61C	109.40
C6C—N1C—H11C	112 (4)	C5C—C6C—H61C	109.32
C2D—N1D—C6D	111.7 (5)	C5C—C6C—H62C	109.39
C2D—N1D—H12D	104 (5)	H61C—C6C—H62C	109.52
C6D—N1D—H11D	106 (3)	N1C—C6C—H62C	109.55
H11D—N1D—H12D	115 (6)	N1D—C2D—C3D	109.9 (5)
C6D—N1D—H12D	110 (5)	C2D—C3D—C4D	111.9 (6)
C2D—N1D—H11D	111 (4)	C3D—C4D—C5D	111.5 (6)
C2E—N1E—C6E	111.5 (5)	C4D—C5D—C6D	111.4 (5)
C6E—N1E—H12E	104 (4)	N1D—C6D—C5D	110.5 (5)
C6E—N1E—H11E	115 (4)	N1D—C2D—H21D	109.42
H11E—N1E—H12E	101 (5)	H21D—C2D—H22D	109.46
C2E—N1E—H12E	117 (4)	C3D—C2D—H22D	109.24
C2E—N1E—H11E	108 (4)	C3D—C2D—H21D	109.38
C2A—C1A—C7A	120.2 (7)	N1D—C2D—H22D	109.40
N71A—C1A—C2A	120.65	C4D—C3D—H31D	108.73
N71A—C1A—C6A	117.12	C2D—C3D—H32D	108.93
C2A—C1A—C6A	122.2 (5)	C2D—C3D—H31D	109.06
C6A—C1A—C7A	117.5 (7)	C4D—C3D—H32D	108.57
O2A—C2A—C1A	123.3 (6)	H31D—C3D—H32D	109.65
C1A—C2A—C3A	116.1 (5)	H41D—C4D—H42D	109.35
O2A—C2A—C3A	120.6 (6)	C3D—C4D—H42D	108.98
C2A—C3A—C4A	121.3 (5)	C5D—C4D—H41D	108.99
N3A—C3A—C4A	117.2 (5)	C5D—C4D—H42D	109.03
N3A—C3A—C2A	121.5 (5)	C3D—C4D—H41D	108.94
C3A—C4A—C5A	120.4 (5)	C4D—C5D—H52D	108.68
N5A—C5A—C6A	120.5 (5)	C4D—C5D—H51D	108.72
C4A—C5A—C6A	121.6 (5)	H51D—C5D—H52D	109.68
N5A—C5A—C4A	117.9 (5)	C6D—C5D—H52D	109.14
O6A—C6A—C5A	132.0 (12)	C6D—C5D—H51D	109.16
O6A—C6A—C1A	109.7 (11)	C5D—C6D—H61D	109.05
C1A—C6A—C5A	118.4 (5)	N1D—C6D—H62D	109.31
O72A—C7A—C1A	121.8 (9)	N1D—C6D—H61D	109.15
O71A—C7A—O72A	119.6 (10)	C5D—C6D—H62D	109.38
O71A—C7A—C1A	118.6 (10)	H61D—C6D—H62D	109.43
C1A—C2A—H2A	122.15	N1E—C2E—C3E	110.3 (6)
C3A—C2A—H2A	121.75	C2E—C3E—C4E	111.4 (8)
C3A—C4A—H4A	119.65	C3E—C4E—C5E	110.3 (8)
C5A—C4A—H4A	119.99	C4E—C5E—C6E	110.8 (8)
C5A—C6A—H6A	120.76	N1E—C6E—C5E	110.1 (7)
C1A—C6A—H6A	120.86	N1E—C2E—H21E	109.27
C6B—C1B—C7B	118.5 (5)	C3E—C2E—H22E	109.32
C2B—C1B—C7B	121.2 (4)	N1E—C2E—H22E	109.40
C2B—C1B—C6B	120.3 (4)	H22E—C2E—H21E	109.39
O2B—C2B—C1B	123.0 (5)	C3E—C2E—H21E	109.18
C1B—C2B—C3B	113.8 (4)	C2E—C3E—H31E	108.94
O2B—C2B—C3B	123.2 (5)	C2E—C3E—H32E	108.89
N3B—C3B—C4B	115.7 (5)	C4E—C3E—H32E	108.94
C2B—C3B—C4B	123.8 (5)	H31E—C3E—H32E	109.60
N3B—C3B—C2B	120.5 (5)	C4E—C3E—H31E	109.02
C3B—C4B—C5B	119.3 (5)	C3E—C4E—H42E	109.25
N5B—C5B—C6B	120.0 (5)	C5E—C4E—H41E	109.26
C4B—C5B—C6B	120.5 (5)	C5E—C4E—H42E	109.75
N5B—C5B—C4B	119.5 (4)	H41E—C4E—H42E	109.44
C1B—C6B—C5B	122.2 (4)	C3E—C4E—H41E	108.86
O71B—C7B—O72B	122.7 (5)	C4E—C5E—H52E	108.89
O71B—C7B—C1B	116.7 (4)	C6E—C5E—H51E	109.31
O72B—C7B—C1B	120.6 (5)	C4E—C5E—H51E	108.78
C5B—C4B—H4B	120.23	H51E—C5E—H52E	109.58
C3B—C4B—H4B	120.44	C6E—C5E—H52E	109.49
C5B—C6B—H6B	118.88	N1E—C6E—H62E	109.33
C1B—C6B—H6B	118.95	N1E—C6E—H61E	109.39
N1C—C2C—C3C	109.9 (5)	C5E—C6E—H61E	109.18
C2C—C3C—C4C	111.9 (7)	H62E—C6E—H61E	109.56
C3C—C4C—C5C	109.5 (6)	C5E—C6E—H62E	109.23
C4C—C5C—C6C	111.0 (6)
O31A—N3A—C3A—C4A	178.6 (5)	N3A—C3A—C4A—C5A	−177.8 (5)
O32A—N3A—C3A—C2A	178.9 (5)	C3A—C4A—C5A—C6A	−1.0 (8)
O31A—N3A—C3A—C2A	−1.3 (8)	C3A—C4A—C5A—N5A	177.6 (5)
O32A—N3A—C3A—C4A	−1.3 (8)	N5A—C5A—C6A—C1A	−179.0 (4)
O51A—N5A—C5A—C6A	173.1 (5)	C4A—C5A—C6A—C1A	−0.5 (7)
O51A—N5A—C5A—C4A	−5.5 (8)	C2B—C1B—C7B—O71B	−165.8 (4)
O52A—N5A—C5A—C6A	−5.5 (8)	C7B—C1B—C2B—O2B	3.3 (6)
O52A—N5A—C5A—C4A	175.9 (5)	C7B—C1B—C2B—C3B	−177.4 (4)
O32B—N3B—C3B—C2B	−169.2 (5)	C6B—C1B—C2B—O2B	−176.3 (4)
O31B—N3B—C3B—C4B	−172.9 (5)	C6B—C1B—C7B—O72B	−164.8 (4)
O32B—N3B—C3B—C4B	8.7 (7)	C2B—C1B—C6B—C5B	−1.1 (6)
O31B—N3B—C3B—C2B	9.2 (8)	C7B—C1B—C6B—C5B	179.3 (4)
O51B—N5B—C5B—C6B	−178.7 (4)	C2B—C1B—C7B—O72B	15.6 (6)
O51B—N5B—C5B—C4B	1.7 (6)	C6B—C1B—C7B—O71B	13.8 (6)
O52B—N5B—C5B—C6B	2.1 (6)	C6B—C1B—C2B—C3B	3.1 (5)
O52B—N5B—C5B—C4B	−177.5 (4)	O2B—C2B—C3B—N3B	−4.6 (7)
C6C—N1C—C2C—C3C	57.2 (7)	C1B—C2B—C3B—N3B	176.0 (4)
C2C—N1C—C6C—C5C	−58.2 (7)	C1B—C2B—C3B—C4B	−1.7 (6)
C6D—N1D—C2D—C3D	−58.4 (7)	O2B—C2B—C3B—C4B	177.7 (4)
C2D—N1D—C6D—C5D	59.0 (7)	N3B—C3B—C4B—C5B	−179.5 (4)
C6E—N1E—C2E—C3E	−58.4 (7)	C2B—C3B—C4B—C5B	−1.7 (7)
C2E—N1E—C6E—C5E	56.8 (8)	C3B—C4B—C5B—N5B	−176.5 (4)
C7A—C1A—C2A—C3A	−178.4 (5)	C3B—C4B—C5B—C6B	3.9 (6)
C2A—C1A—C6A—C5A	1.0 (7)	N5B—C5B—C6B—C1B	177.9 (4)
C7A—C1A—C6A—C5A	179.4 (5)	C4B—C5B—C6B—C1B	−2.5 (6)
C6A—C1A—C2A—O2A	179.6 (5)	N1C—C2C—C3C—C4C	−55.6 (7)
C6A—C1A—C7A—O72A	178.1 (6)	C2C—C3C—C4C—C5C	55.5 (8)
C2A—C1A—C7A—O72A	−3.5 (10)	C3C—C4C—C5C—C6C	−56.2 (8)
C2A—C1A—C7A—O71A	176.7 (5)	C4C—C5C—C6C—N1C	57.3 (7)
C6A—C1A—C2A—C3A	0.0 (7)	N1D—C2D—C3D—C4D	54.9 (8)
C6A—C1A—C7A—O71A	−1.8 (9)	C2D—C3D—C4D—C5D	−52.6 (8)
C7A—C1A—C2A—O2A	1.2 (8)	C3D—C4D—C5D—C6D	52.6 (8)
C1A—C2A—C3A—C4A	−1.6 (7)	C4D—C5D—C6D—N1D	−55.6 (7)
O2A—C2A—C3A—N3A	−1.3 (8)	N1E—C2E—C3E—C4E	58.4 (8)
C1A—C2A—C3A—N3A	178.3 (5)	C2E—C3E—C4E—C5E	−57.0 (10)
O2A—C2A—C3A—C4A	178.8 (5)	C3E—C4E—C5E—C6E	55.1 (11)
C2A—C3A—C4A—C5A	2.1 (8)	C4E—C5E—C6E—N1E	−55.0 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H21A···O72A	0.96 (5)	1.62 (5)	2.586 (8)	177 (5)
O1W—H1W···O71B^i	0.80 (8)	2.03 (8)	2.801 (7)	163 (6)
O1W—H2W···O72B^ii	0.85 (7)	1.85 (7)	2.693 (7)	175 (6)
N1C—H11C···O71A^iii	0.95 (5)	2.46 (5)	3.146 (8)	131 (5)
N1C—H11C···O72A^iii	0.95 (5)	2.35 (5)	3.165 (8)	146 (5)
N1C—H11C···O71B^iii	0.95 (5)	2.55 (5)	3.156 (7)	122 (4)
N1C—H12C···O71B^iv	0.95 (6)	1.86 (6)	2.797 (6)	168 (6)
N1D—H11D···O2A^i	0.95 (7)	1.99 (6)	2.892 (8)	158 (5)
N1D—H12D···O1W	0.97 (8)	1.74 (8)	2.704 (8)	171 (8)
N1E—H11E···O2B^ii	0.97 (7)	1.92 (7)	2.782 (6)	138 (6)
N1E—H11E···O72B^ii	0.97 (7)	2.12 (8)	2.908 (7)	139 (6)
N1E—H12E···O2B	0.88 (6)	1.95 (6)	2.794 (7)	162 (6)
N1E—H12E···O31B	0.88 (6)	2.57 (6)	3.184 (7)	126 (5)
C4A—H4A···O32A	0.95	2.41	2.738 (7)	100
C6B—H6B···O71B	0.95	2.40	2.745 (6)	101
C2E—H21E···O52A	0.95	2.56	3.416 (8)	150
C2D—H22D···O52B^i	0.95	2.51	3.082 (8)	119

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