Buy article online - an online subscription or single-article purchase is required to access this article.
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.
Supporting information
CCDC reference: 298708
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean (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
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
top
Crystal data top
3C5H12N+·C7H2N2O72−·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) Å3 | 0.30 × 0.25 × 0.20 mm |
Data collection top
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 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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.211 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.2218P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O71Bi | 0.80 (8) | 2.03 (8) | 2.801 (7) | 163 (6) |
O1W—H2W···O72Bii | 0.85 (7) | 1.85 (7) | 2.693 (7) | 175 (6) |
N1C—H11C···O71Aiii | 0.95 (5) | 2.46 (5) | 3.146 (8) | 131 (5) |
N1C—H11C···O72Aiii | 0.95 (5) | 2.35 (5) | 3.165 (8) | 146 (5) |
N1C—H11C···O71Biii | 0.95 (5) | 2.55 (5) | 3.156 (7) | 122 (4) |
N1C—H12C···O71Biv | 0.95 (6) | 1.86 (6) | 2.797 (6) | 168 (6) |
N1D—H11D···O2Ai | 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···O2Bii | 0.97 (7) | 1.92 (7) | 2.782 (6) | 138 (6) |
N1E—H11E···O72Bii | 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···O52Bi | 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. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.