The crystal structure of adenosinium 3,5-dinitrosalicylicate, C10H14N5O4+·C7H3N2O7−, shows the presence of a primary chain structure formed through homomeric head-to-tail cyclic R22(10) hydrogen-bonding interactions between hydroxy O- and both purine and amine N-donor and acceptor groups of the furanose and purine moieties of the adenosinium species. These chain structures are related by crystallographic 21 symmetry. Secondary hetero-ionic hydrogen bonding, involving the 3,5-dinitrosalicylate anion, including a cyclic R22(8) interaction between the carboxylate group and the protonated purine and amine groups of the adenosinium cation are also present, together with heteromolecular π–π interactions giving a three-dimensional hydrogen-bonded polymer structure.
Supporting information
CCDC reference: 251735
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.036
- wR factor = 0.122
- Data-to-parameter ratio = 7.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.59
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
Alert level G
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 27.49
From the CIF: _reflns_number_total 2406
Count of symmetry unique reflns 2405
Completeness (_total/calc) 100.04%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 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: SIR92 (Altomare, 1994); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.
adenosinium 3,5-dinitrosalicylate
top
Crystal data top
C10H14N5O4+·C7H3N2O7− | F(000) = 512 |
Mr = 495.38 | Dx = 1.670 Mg m−3 |
Monoclinic, P21 | Melting point = 487.2–488.5 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71069 Å |
a = 15.297 (2) Å | Cell parameters from 25 reflections |
b = 8.8543 (14) Å | θ = 12.5–16.9° |
c = 7.2805 (8) Å | µ = 0.14 mm−1 |
β = 92.321 (10)° | T = 298 K |
V = 985.3 (2) Å3 | Plate, pale yellow |
Z = 2 | 0.40 × 0.35 × 0.03 mm |
Data collection top
Rigaku AFC-7R diffractometer | 1873 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.018 |
Graphite monochromator | θmax = 27.5°, θmin = 2.7° |
ω–2θ scans | h = −8→19 |
Absorption correction: ψ scan (TEXSAN for Windows; Molecular Structure Corporation, 1999) | k = 0→11 |
Tmin = 0.945, Tmax = 0.995 | l = −9→9 |
2690 measured reflections | 3 standard reflections every 150 min |
2406 independent reflections | intensity decay: 0.0% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters not refined |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.1P)2 + 2.5029P] where P = (Fo2 + 2Fc2)/3 |
S = 0.88 | (Δ/σ)max = 0.003 |
2406 reflections | Δρmax = 0.20 e Å−3 |
317 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (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 >
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 | Uiso*/Ueq | |
O2 | 0.60981 (18) | 0.1756 (4) | 0.3497 (5) | 0.0449 (10) | |
O3A | 0.6826 (2) | −0.0660 (4) | 0.5133 (5) | 0.0530 (11) | |
O3B | 0.8175 (2) | −0.0836 (4) | 0.4380 (5) | 0.0516 (11) | |
O5A | 0.9774 (2) | 0.3746 (4) | 0.6546 (5) | 0.0581 (11) | |
O5B | 0.9495 (2) | 0.5597 (4) | 0.4672 (4) | 0.0505 (10) | |
O7A | 0.62995 (19) | 0.6321 (3) | 0.2930 (5) | 0.0420 (9) | |
O7B | 0.54980 (18) | 0.4236 (4) | 0.2720 (5) | 0.0493 (10) | |
N3 | 0.7517 (2) | −0.0119 (4) | 0.4699 (5) | 0.0380 (10) | |
N5 | 0.9304 (2) | 0.4413 (4) | 0.5402 (5) | 0.0380 (10) | |
C1 | 0.6965 (2) | 0.3985 (4) | 0.3833 (5) | 0.0276 (10) | |
C2 | 0.6854 (2) | 0.2404 (5) | 0.3972 (5) | 0.0312 (11) | |
C3 | 0.7581 (3) | 0.1533 (4) | 0.4576 (5) | 0.0318 (11) | |
C4 | 0.8377 (3) | 0.2184 (5) | 0.5037 (5) | 0.0337 (11) | |
C5 | 0.8454 (2) | 0.3730 (5) | 0.4892 (5) | 0.0302 (10) | |
C6 | 0.7761 (2) | 0.4645 (4) | 0.4297 (5) | 0.0295 (10) | |
C7 | 0.6208 (2) | 0.4938 (5) | 0.3118 (6) | 0.0323 (11) | |
O21 | 0.70934 (18) | 0.8539 (3) | 1.0866 (4) | 0.0360 (8) | |
O31 | 0.8179 (2) | 1.0044 (3) | 0.8598 (4) | 0.0419 (9) | |
O41 | 0.84577 (16) | 0.6698 (3) | 0.7672 (4) | 0.0320 (8) | |
O51 | 0.9662 (2) | 0.6129 (4) | 1.0694 (5) | 0.0490 (10) | |
N12 | 0.5273 (2) | 0.2793 (4) | 0.7750 (5) | 0.0348 (10) | |
N32 | 0.5874 (2) | 0.5264 (4) | 0.7650 (5) | 0.0359 (10) | |
N62 | 0.5965 (2) | 0.0651 (4) | 0.8899 (5) | 0.0393 (10) | |
N72 | 0.75235 (19) | 0.2820 (4) | 0.9702 (4) | 0.0303 (9) | |
N92 | 0.73744 (19) | 0.5268 (4) | 0.8934 (4) | 0.0285 (8) | |
C11 | 0.7654 (2) | 0.6817 (4) | 0.8549 (5) | 0.0276 (9) | |
C21 | 0.7839 (2) | 0.7775 (4) | 1.0275 (5) | 0.0285 (10) | |
C22 | 0.5248 (2) | 0.4296 (5) | 0.7334 (6) | 0.0377 (11) | |
C31 | 0.8551 (2) | 0.8849 (4) | 0.9644 (5) | 0.0306 (10) | |
C41 | 0.9063 (2) | 0.7848 (4) | 0.8354 (5) | 0.0310 (10) | |
C42 | 0.6591 (2) | 0.4599 (4) | 0.8464 (5) | 0.0278 (10) | |
C51 | 0.9868 (3) | 0.7075 (5) | 0.9208 (7) | 0.0429 (14) | |
C52 | 0.6693 (2) | 0.3099 (4) | 0.8945 (5) | 0.0289 (10) | |
C62 | 0.5992 (2) | 0.2097 (4) | 0.8555 (5) | 0.0288 (10) | |
C82 | 0.7898 (2) | 0.4153 (5) | 0.9659 (6) | 0.0319 (11) | |
H2 | 0.568400 | 0.250100 | 0.328000 | 0.0330* | |
H4 | 0.885900 | 0.157900 | 0.546000 | 0.0400* | |
H6 | 0.783800 | 0.571500 | 0.417800 | 0.0340* | |
H11 | 0.723100 | 0.731000 | 0.775300 | 0.0330* | |
H12 | 0.479500 | 0.221500 | 0.751400 | 0.0330* | |
H21 | 0.807500 | 0.713800 | 1.123300 | 0.0340* | |
H21A | 0.689600 | 0.789700 | 1.173100 | 0.0330* | |
H22 | 0.471300 | 0.468100 | 0.676900 | 0.0450* | |
H31 | 0.891300 | 0.920600 | 1.065600 | 0.0350* | |
H31A | 0.808700 | 1.090900 | 0.929000 | 0.0330* | |
H41 | 0.923100 | 0.844900 | 0.733800 | 0.0370* | |
H51A | 1.028000 | 0.782700 | 0.963100 | 0.0540* | |
H51B | 1.013900 | 0.648000 | 0.829000 | 0.0540* | |
H51C | 0.983800 | 0.649000 | 1.164000 | 0.0330* | |
H62A | 0.642600 | 0.026000 | 0.936100 | 0.0330* | |
H62B | 0.553200 | 0.007600 | 0.846600 | 0.0330* | |
H82 | 0.849500 | 0.432800 | 1.010400 | 0.0380* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0298 (14) | 0.0317 (15) | 0.072 (2) | −0.0026 (12) | −0.0143 (13) | 0.0037 (15) |
O3A | 0.0529 (19) | 0.0355 (17) | 0.070 (2) | −0.0073 (15) | −0.0059 (16) | 0.0095 (16) |
O3B | 0.0544 (19) | 0.0373 (17) | 0.062 (2) | 0.0159 (16) | −0.0127 (16) | −0.0100 (16) |
O5A | 0.0405 (16) | 0.049 (2) | 0.082 (2) | 0.0012 (16) | −0.0312 (17) | −0.0012 (18) |
O5B | 0.0396 (16) | 0.056 (2) | 0.0559 (18) | −0.0174 (16) | 0.0034 (14) | 0.0052 (17) |
O7A | 0.0332 (14) | 0.0321 (15) | 0.0603 (19) | 0.0047 (12) | −0.0028 (13) | 0.0084 (14) |
O7B | 0.0291 (14) | 0.0352 (16) | 0.082 (2) | 0.0028 (13) | −0.0187 (14) | 0.0063 (17) |
N3 | 0.0424 (18) | 0.0295 (18) | 0.0408 (18) | 0.0044 (15) | −0.0128 (15) | −0.0019 (15) |
N5 | 0.0273 (15) | 0.040 (2) | 0.0463 (19) | −0.0027 (15) | −0.0022 (13) | −0.0101 (16) |
C1 | 0.0244 (16) | 0.0275 (18) | 0.0305 (17) | 0.0008 (14) | −0.0022 (13) | 0.0004 (14) |
C2 | 0.0258 (17) | 0.0282 (19) | 0.039 (2) | 0.0002 (15) | −0.0052 (14) | −0.0009 (15) |
C3 | 0.0362 (19) | 0.0261 (19) | 0.0327 (18) | 0.0012 (15) | −0.0041 (15) | −0.0019 (15) |
C4 | 0.0275 (17) | 0.036 (2) | 0.037 (2) | 0.0072 (16) | −0.0050 (15) | −0.0006 (16) |
C5 | 0.0239 (16) | 0.035 (2) | 0.0316 (18) | −0.0004 (15) | −0.0017 (14) | −0.0027 (16) |
C6 | 0.0284 (17) | 0.0265 (18) | 0.0332 (18) | −0.0021 (14) | −0.0033 (14) | 0.0007 (15) |
C7 | 0.0265 (17) | 0.029 (2) | 0.041 (2) | 0.0044 (15) | −0.0029 (14) | 0.0025 (16) |
O21 | 0.0350 (13) | 0.0297 (14) | 0.0437 (15) | 0.0050 (12) | 0.0047 (12) | 0.0019 (12) |
O31 | 0.0592 (18) | 0.0221 (14) | 0.0441 (15) | 0.0053 (14) | −0.0022 (13) | 0.0014 (13) |
O41 | 0.0267 (12) | 0.0295 (13) | 0.0398 (14) | −0.0051 (11) | 0.0026 (10) | −0.0076 (12) |
O51 | 0.0490 (17) | 0.0401 (18) | 0.0561 (18) | 0.0072 (15) | −0.0186 (14) | 0.0025 (15) |
N12 | 0.0241 (14) | 0.0270 (16) | 0.0528 (19) | −0.0031 (13) | −0.0063 (13) | −0.0015 (15) |
N32 | 0.0261 (15) | 0.0299 (17) | 0.051 (2) | 0.0011 (13) | −0.0073 (13) | 0.0040 (15) |
N62 | 0.0280 (16) | 0.0289 (17) | 0.060 (2) | −0.0053 (14) | −0.0111 (15) | −0.0030 (16) |
N72 | 0.0269 (14) | 0.0246 (15) | 0.0388 (16) | 0.0020 (13) | −0.0075 (12) | −0.0024 (13) |
N92 | 0.0240 (14) | 0.0221 (14) | 0.0391 (16) | 0.0011 (12) | −0.0025 (12) | −0.0015 (13) |
C11 | 0.0241 (15) | 0.0246 (17) | 0.0339 (17) | 0.0013 (14) | −0.0027 (13) | −0.0006 (15) |
C21 | 0.0284 (17) | 0.0241 (17) | 0.0327 (17) | 0.0029 (15) | −0.0020 (13) | 0.0014 (15) |
C22 | 0.0272 (18) | 0.0280 (19) | 0.057 (2) | 0.0040 (16) | −0.0078 (16) | 0.0013 (18) |
C31 | 0.0311 (17) | 0.0235 (17) | 0.0367 (18) | −0.0055 (14) | −0.0056 (14) | −0.0038 (15) |
C41 | 0.0282 (17) | 0.0240 (17) | 0.0407 (19) | −0.0071 (15) | 0.0012 (14) | 0.0005 (16) |
C42 | 0.0237 (15) | 0.0260 (18) | 0.0336 (17) | 0.0011 (14) | −0.0009 (13) | −0.0027 (14) |
C51 | 0.0281 (19) | 0.037 (2) | 0.063 (3) | −0.0012 (17) | −0.0074 (17) | −0.002 (2) |
C52 | 0.0249 (16) | 0.0237 (18) | 0.0380 (18) | −0.0006 (14) | −0.0001 (14) | −0.0018 (15) |
C62 | 0.0264 (17) | 0.0233 (18) | 0.0364 (18) | −0.0001 (14) | −0.0014 (14) | −0.0043 (15) |
C82 | 0.0268 (17) | 0.0275 (18) | 0.041 (2) | 0.0029 (15) | −0.0049 (14) | 0.0008 (16) |
Geometric parameters (Å, º) top
O2—C2 | 1.324 (5) | N92—C11 | 1.467 (5) |
O3A—N3 | 1.214 (5) | N12—H12 | 0.9033 |
O3B—N3 | 1.220 (5) | N62—H62B | 0.8834 |
O5A—N5 | 1.229 (5) | N62—H62A | 0.8433 |
O5B—N5 | 1.216 (5) | C1—C2 | 1.414 (6) |
O7A—C7 | 1.241 (5) | C1—C7 | 1.508 (5) |
O7B—C7 | 1.275 (5) | C1—C6 | 1.380 (5) |
O2—H2 | 0.9237 | C2—C3 | 1.409 (6) |
O21—C21 | 1.408 (4) | C3—C4 | 1.376 (6) |
O31—C31 | 1.410 (4) | C4—C5 | 1.378 (6) |
O41—C11 | 1.412 (4) | C5—C6 | 1.389 (5) |
O41—C41 | 1.450 (4) | C4—H4 | 0.9524 |
O51—C51 | 1.414 (6) | C6—H6 | 0.9591 |
O21—H21A | 0.9090 | C11—C21 | 1.533 (5) |
O31—H31A | 0.9306 | C21—C31 | 1.530 (5) |
O51—H51C | 0.7962 | C31—C41 | 1.530 (5) |
N3—C3 | 1.469 (5) | C41—C51 | 1.520 (6) |
N5—C5 | 1.468 (5) | C42—C52 | 1.381 (5) |
N12—C62 | 1.371 (5) | C52—C62 | 1.412 (5) |
N12—C22 | 1.365 (6) | C11—H11 | 0.9564 |
N32—C42 | 1.359 (5) | C21—H21 | 0.9563 |
N32—C22 | 1.299 (5) | C22—H22 | 0.9633 |
N62—C62 | 1.306 (5) | C31—H31 | 0.9573 |
N72—C52 | 1.386 (4) | C41—H41 | 0.9549 |
N72—C82 | 1.313 (5) | C51—H51A | 0.9590 |
N92—C42 | 1.368 (4) | C51—H51B | 0.9584 |
N92—C82 | 1.364 (5) | C82—H82 | 0.9690 |
| | | |
C2—O2—H2 | 108.71 | N72—C52—C62 | 130.1 (3) |
C11—O41—C41 | 110.4 (3) | C42—C52—C62 | 118.4 (3) |
C21—O21—H21A | 101.96 | N72—C52—C42 | 111.4 (3) |
C31—O31—H31A | 113.07 | N12—C62—N62 | 119.4 (3) |
C51—O51—H51C | 110.00 | N62—C62—C52 | 127.4 (3) |
O3B—N3—C3 | 116.7 (3) | N12—C62—C52 | 113.1 (3) |
O3A—N3—C3 | 118.0 (3) | N72—C82—N92 | 114.2 (3) |
O3A—N3—O3B | 125.3 (4) | O41—C11—H11 | 109.89 |
O5B—N5—C5 | 118.1 (3) | N92—C11—H11 | 110.31 |
O5A—N5—O5B | 124.5 (3) | C21—C11—H11 | 110.00 |
O5A—N5—C5 | 117.5 (3) | O21—C21—H21 | 110.30 |
C22—N12—C62 | 123.2 (3) | C11—C21—H21 | 108.86 |
C22—N32—C42 | 111.6 (3) | C31—C21—H21 | 109.46 |
C52—N72—C82 | 102.9 (3) | N12—C22—H22 | 117.09 |
C11—N92—C82 | 125.4 (3) | N32—C22—H22 | 116.72 |
C11—N92—C42 | 128.0 (3) | O31—C31—H31 | 112.09 |
C42—N92—C82 | 106.1 (3) | C21—C31—H31 | 111.76 |
O21—C21—C11 | 113.0 (3) | C41—C31—H31 | 111.67 |
N12—C22—N32 | 126.2 (3) | O41—C41—H41 | 108.31 |
O31—C31—C21 | 110.6 (3) | C31—C41—H41 | 108.25 |
O31—C31—C41 | 108.0 (3) | C51—C41—H41 | 109.20 |
C21—C31—C41 | 102.3 (3) | O51—C51—H51A | 109.24 |
O41—C41—C31 | 106.3 (2) | O51—C51—H51B | 108.91 |
O41—C41—C51 | 108.6 (3) | C41—C51—H51A | 109.26 |
C31—C41—C51 | 115.9 (3) | C41—C51—H51B | 109.18 |
N32—C42—N92 | 127.2 (3) | H51A—C51—H51B | 107.96 |
N32—C42—C52 | 127.4 (3) | N72—C82—H82 | 122.82 |
N92—C42—C52 | 105.3 (3) | N92—C82—H82 | 122.98 |
O51—C51—C41 | 112.2 (4) | | |
| | | |
C41—O41—C11—C21 | −17.4 (4) | C7—C1—C2—O2 | −0.4 (5) |
C11—O41—C41—C31 | −5.4 (4) | C7—C1—C2—C3 | 177.6 (3) |
C41—O41—C11—N92 | −139.1 (3) | C7—C1—C6—C5 | −177.8 (3) |
C11—O41—C41—C51 | 119.9 (3) | C2—C1—C7—O7B | 1.6 (5) |
O3B—N3—C3—C4 | −32.0 (5) | O2—C2—C3—C4 | 178.6 (4) |
O3A—N3—C3—C2 | −34.3 (5) | O2—C2—C3—N3 | −0.2 (6) |
O3B—N3—C3—C2 | 146.8 (4) | C1—C2—C3—N3 | −178.2 (3) |
O3A—N3—C3—C4 | 146.9 (4) | C1—C2—C3—C4 | 0.6 (5) |
O5A—N5—C5—C4 | −27.6 (5) | N3—C3—C4—C5 | 178.6 (3) |
O5A—N5—C5—C6 | 152.0 (4) | C2—C3—C4—C5 | −0.1 (6) |
O5B—N5—C5—C4 | 152.6 (4) | C3—C4—C5—C6 | −0.1 (6) |
O5B—N5—C5—C6 | −27.8 (5) | C3—C4—C5—N5 | 179.5 (4) |
C62—N12—C22—N32 | −1.0 (7) | C4—C5—C6—C1 | 0.0 (6) |
C22—N12—C62—C52 | 1.4 (5) | N5—C5—C6—C1 | −179.6 (3) |
C22—N12—C62—N62 | −179.6 (4) | N92—C11—C21—O21 | −89.0 (3) |
C42—N32—C22—N12 | 0.4 (6) | O41—C11—C21—C31 | 32.8 (3) |
C22—N32—C42—C52 | −0.2 (6) | O41—C11—C21—O21 | 154.2 (3) |
C22—N32—C42—N92 | 177.8 (4) | N92—C11—C21—C31 | 149.5 (3) |
C82—N72—C52—C62 | 177.2 (4) | O21—C21—C31—O31 | −41.5 (4) |
C52—N72—C82—N92 | 0.0 (4) | O21—C21—C31—C41 | −156.3 (3) |
C82—N72—C52—C42 | 0.1 (4) | C11—C21—C31—C41 | −34.7 (3) |
C11—N92—C42—C52 | 173.1 (3) | C11—C21—C31—O31 | 80.1 (3) |
C82—N92—C11—C21 | −71.4 (4) | O31—C31—C41—C51 | 148.1 (3) |
C11—N92—C42—N32 | −5.3 (6) | O31—C31—C41—O41 | −91.1 (3) |
C42—N92—C11—C21 | 116.9 (4) | C21—C31—C41—O41 | 25.6 (3) |
C82—N92—C42—N32 | −178.3 (4) | C21—C31—C41—C51 | −95.2 (3) |
C42—N92—C11—O41 | −126.6 (3) | O41—C41—C51—O51 | −60.4 (4) |
C82—N92—C42—C52 | 0.1 (4) | C31—C41—C51—O51 | 59.2 (5) |
C11—N92—C82—N72 | −173.3 (3) | N92—C42—C52—C62 | −177.6 (3) |
C42—N92—C82—N72 | 0.0 (4) | N92—C42—C52—N72 | −0.1 (4) |
C82—N92—C11—O41 | 45.2 (5) | N32—C42—C52—N72 | 178.3 (4) |
C6—C1—C2—O2 | −178.7 (4) | N32—C42—C52—C62 | 0.7 (6) |
C6—C1—C2—C3 | −0.7 (5) | N72—C52—C62—N62 | 2.8 (7) |
C6—C1—C7—O7A | 0.6 (6) | C42—C52—C62—N12 | −1.2 (5) |
C6—C1—C7—O7B | 179.9 (5) | C42—C52—C62—N62 | 179.9 (5) |
C2—C1—C7—O7A | −177.7 (4) | N72—C52—C62—N12 | −178.2 (4) |
C2—C1—C6—C5 | 0.4 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O7B | 0.92 | 1.61 | 2.438 (5) | 147 |
N12—H12···O7Ai | 0.90 | 1.87 | 2.763 (4) | 170 |
N62—H62B···O7Bi | 0.88 | 1.92 | 2.785 (5) | 167 |
O21—H21A···O7Aii | 0.91 | 1.90 | 2.782 (4) | 163 |
O51—H51C···O5Bii | 0.80 | 2.42 | 2.955 (5) | 125 |
O31—H31A···N72iii | 0.93 | 1.93 | 2.785 (4) | 152 |
O51—H51C···O5Aiv | 0.80 | 2.45 | 3.164 (5) | 149 |
N62—H62A···O21v | 0.84 | 2.12 | 2.886 (4) | 152 |
C22—H22···O2vi | 0.96 | 2.22 | 3.041 (5) | 142 |
C82—H82···O51 | 0.97 | 2.42 | 3.278 (5) | 148 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x, y, z+1; (iii) x, y+1, z; (iv) −x+2, y+1/2, −z+2; (v) x, y−1, z; (vi) −x+1, y+1/2, −z+1. |