The structure of title co-crystal consists of a 2,3,5,6-tetrakis(pyridin-2-yl)pyrazine coformer and hydrogen peroxide solvent molecules in a ratio of 1:4.75.
Supporting information
CCDC reference: 1581165
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.090
- wR factor = 0.191
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00609 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 15.693 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 3.134 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.596 18 Report
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 7 Note
PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 15 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ... 0.50 Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 10.00 Why ?
PLAT300_ALERT_4_G Atom Site Occupancy of O61 is Constrained at 0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H61 is Constrained at 0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 2).. 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 3).. 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 4).. 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 7).. 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 8).. 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 9).. 100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 10).. 100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 3.38) in Resd. # 2 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 3.56) in Resd. # 4 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 0.62) in Resd. # 7 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 0.44) in Resd. # 9 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 3 Note
PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2016 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still 66% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
24 ALERT level G = General information/check it is not something unexpected
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
14 ALERT type 4 Improvement, methodology, query or suggestion
2 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
2,3,5,6-Tetrakis(pyridin-2-yl)pyrazine
hydrogen peroxide 4.75-solvate
top
Crystal data top
C24H16N6·4.75H2O2 | F(000) = 1150 |
Mr = 550.00 | Dx = 1.414 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5939 reflections |
a = 19.000 (7) Å | θ = 2.2–30.1° |
b = 7.382 (3) Å | µ = 0.11 mm−1 |
c = 20.212 (7) Å | T = 150 K |
β = 114.271 (5)° | Prism, colourless |
V = 2584.3 (16) Å3 | 0.40 × 0.40 × 0.30 mm |
Z = 4 | |
Data collection top
Bruker SMART APEXII diffractometer | 4563 independent reflections |
Radiation source: fine-focus sealed tube | 3870 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scans | θmax = 25.1°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −22→22 |
Tmin = 0.957, Tmax = 0.967 | k = −8→8 |
16397 measured reflections | l = −24→23 |
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)] = 0.090 | H-atom parameters constrained |
wR(F2) = 0.191 | w = 1/[σ2(Fo2) + (0.010P)2 + 10.P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
4563 reflections | Δρmax = 0.39 e Å−3 |
388 parameters | Δρmin = −0.36 e Å−3 |
3 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0017 (4) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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) |
O11 | 0.3518 (4) | −0.0660 (7) | 0.4736 (3) | 0.0662 (16) | 0.846 (9) |
H11 | 0.3640 | −0.0353 | 0.5148 | 0.099* | 0.846 (9) |
O12 | 0.3037 (3) | 0.0865 (7) | 0.4355 (3) | 0.0500 (13) | 0.846 (9) |
H12 | 0.2602 | 0.0537 | 0.4129 | 0.075* | 0.846 (9) |
O13 | 0.302 (2) | −0.084 (3) | 0.4427 (16) | 0.0662 (16) | 0.154 (9) |
H13 | 0.2574 | −0.0674 | 0.4170 | 0.099* | 0.154 (9) |
O14 | 0.325 (2) | 0.101 (4) | 0.4650 (18) | 0.0500 (13) | 0.154 (9) |
H14 | 0.3448 | 0.0846 | 0.5079 | 0.075* | 0.154 (9) |
O21 | 0.1982 (4) | 0.8976 (8) | 0.5494 (5) | 0.046 (2) | 0.75 (2) |
H21 | 0.2428 | 0.9008 | 0.5768 | 0.068* | 0.75 (2) |
O22 | 0.1750 (5) | 1.0887 (9) | 0.5388 (5) | 0.045 (2) | 0.75 (2) |
H22 | 0.1578 | 1.0953 | 0.4955 | 0.068* | 0.75 (2) |
O23 | 0.2088 (15) | 1.053 (3) | 0.5761 (17) | 0.054 (6) | 0.25 (2) |
H23 | 0.2513 | 1.0114 | 0.5961 | 0.081* | 0.25 (2) |
O24 | 0.1651 (17) | 0.951 (3) | 0.5117 (15) | 0.056 (7) | 0.25 (2) |
H24 | 0.1496 | 0.9992 | 0.4729 | 0.084* | 0.25 (2) |
O31 | 0.0252 (3) | 0.9210 (7) | 0.5133 (3) | 0.0661 (17) | 0.891 (9) |
H31 | 0.0661 | 0.9677 | 0.5224 | 0.099* | 0.891 (9) |
O32 | −0.014 (2) | 0.952 (6) | 0.4653 (14) | 0.0661 (17) | 0.109 (9) |
H32 | 0.0309 | 0.9595 | 0.4745 | 0.099* | 0.109 (9) |
O41 | 0.15205 (18) | 0.9727 (4) | 0.35656 (18) | 0.0412 (8) | |
H41 | 0.1267 | 0.8912 | 0.3612 | 0.062* | |
O42 | 0.1137 (2) | 1.1114 (4) | 0.38369 (18) | 0.0440 (9) | |
H42 | 0.1200 | 1.1955 | 0.3618 | 0.066* | |
O51 | 0.35556 (18) | 0.9097 (5) | 0.64562 (18) | 0.0438 (8) | |
H51 | 0.3802 | 0.8260 | 0.6415 | 0.066* | |
O52 | 0.3959 (2) | 1.0412 (5) | 0.61765 (18) | 0.0496 (9) | |
H52 | 0.3851 | 1.1264 | 0.6362 | 0.074* | |
O61 | 0.4922 (9) | −0.0768 (15) | 0.5192 (8) | 0.149 (6)* | 0.50 |
H61 | 0.4462 | −0.0750 | 0.5046 | 0.224* | 0.50 |
N1 | 0.35882 (19) | 0.3326 (5) | 0.68106 (18) | 0.0299 (8) | |
N2 | 0.43995 (19) | 0.6236 (5) | 0.63149 (18) | 0.0310 (8) | |
N3 | 0.06552 (18) | 0.6947 (5) | 0.37238 (18) | 0.0276 (8) | |
N4 | 0.13565 (19) | 0.4025 (5) | 0.30774 (17) | 0.0270 (8) | |
N5 | 0.19869 (18) | 0.5011 (5) | 0.53122 (17) | 0.0232 (7) | |
N6 | 0.29935 (18) | 0.5095 (5) | 0.46312 (17) | 0.0243 (7) | |
C11 | 0.2751 (2) | 0.4834 (6) | 0.5698 (2) | 0.0242 (9) | |
C12 | 0.3013 (2) | 0.4523 (6) | 0.6494 (2) | 0.0255 (9) | |
C13 | 0.2670 (2) | 0.5469 (6) | 0.6880 (2) | 0.0307 (10) | |
H13A | 0.2254 | 0.6277 | 0.6639 | 0.037* | |
C14 | 0.2949 (3) | 0.5205 (7) | 0.7624 (2) | 0.0374 (11) | |
H14A | 0.2723 | 0.5826 | 0.7900 | 0.045* | |
C15 | 0.3561 (3) | 0.4026 (7) | 0.7959 (2) | 0.0414 (12) | |
H15A | 0.3772 | 0.3847 | 0.8470 | 0.050* | |
C16 | 0.3856 (3) | 0.3116 (7) | 0.7531 (2) | 0.0375 (11) | |
H16A | 0.4271 | 0.2296 | 0.7761 | 0.045* | |
C21 | 0.3263 (2) | 0.4994 (6) | 0.5354 (2) | 0.0248 (9) | |
C22 | 0.4120 (2) | 0.5050 (6) | 0.5756 (2) | 0.0287 (9) | |
C23 | 0.4586 (2) | 0.3985 (7) | 0.5539 (2) | 0.0329 (10) | |
H23A | 0.4367 | 0.3177 | 0.5140 | 0.039* | |
C24 | 0.5380 (2) | 0.4123 (7) | 0.5916 (2) | 0.0380 (11) | |
H24A | 0.5716 | 0.3398 | 0.5784 | 0.046* | |
C25 | 0.5674 (2) | 0.5328 (8) | 0.6485 (3) | 0.0444 (13) | |
H25A | 0.6217 | 0.5459 | 0.6747 | 0.053* | |
C26 | 0.5169 (2) | 0.6350 (7) | 0.6671 (3) | 0.0396 (11) | |
H26A | 0.5378 | 0.7166 | 0.7068 | 0.048* | |
C31 | 0.1721 (2) | 0.5232 (5) | 0.45945 (19) | 0.0199 (8) | |
C32 | 0.0876 (2) | 0.5562 (5) | 0.42050 (19) | 0.0215 (8) | |
C33 | 0.0354 (2) | 0.4529 (6) | 0.4356 (2) | 0.0240 (9) | |
H33A | 0.0530 | 0.3572 | 0.4700 | 0.029* | |
C34 | −0.0424 (2) | 0.4894 (6) | 0.4006 (2) | 0.0283 (9) | |
H34A | −0.0791 | 0.4196 | 0.4102 | 0.034* | |
C35 | −0.0658 (2) | 0.6309 (7) | 0.3507 (2) | 0.0371 (11) | |
H35A | −0.1190 | 0.6598 | 0.3256 | 0.045* | |
C36 | −0.0101 (2) | 0.7290 (7) | 0.3384 (2) | 0.0356 (11) | |
H36A | −0.0265 | 0.8252 | 0.3042 | 0.043* | |
C41 | 0.2231 (2) | 0.5160 (5) | 0.4245 (2) | 0.0217 (8) | |
C42 | 0.1960 (2) | 0.5127 (6) | 0.3444 (2) | 0.0249 (9) | |
C43 | 0.2327 (2) | 0.6153 (6) | 0.3100 (2) | 0.0294 (9) | |
H43A | 0.2757 | 0.6893 | 0.3376 | 0.035* | |
C44 | 0.2056 (2) | 0.6080 (7) | 0.2353 (2) | 0.0334 (10) | |
H44A | 0.2299 | 0.6763 | 0.2107 | 0.040* | |
C45 | 0.1427 (3) | 0.4993 (7) | 0.1970 (2) | 0.0372 (11) | |
H45A | 0.1225 | 0.4932 | 0.1456 | 0.045* | |
C46 | 0.1094 (3) | 0.3989 (6) | 0.2350 (2) | 0.0329 (10) | |
H46A | 0.0662 | 0.3245 | 0.2083 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O11 | 0.075 (4) | 0.052 (3) | 0.057 (3) | 0.014 (3) | 0.013 (3) | −0.001 (2) |
O12 | 0.053 (3) | 0.051 (3) | 0.046 (3) | −0.002 (2) | 0.020 (3) | 0.005 (3) |
O13 | 0.075 (4) | 0.052 (3) | 0.057 (3) | 0.014 (3) | 0.013 (3) | −0.001 (2) |
O14 | 0.053 (3) | 0.051 (3) | 0.046 (3) | −0.002 (2) | 0.020 (3) | 0.005 (3) |
O21 | 0.045 (3) | 0.022 (3) | 0.062 (5) | 0.006 (2) | 0.015 (3) | 0.009 (3) |
O22 | 0.054 (5) | 0.034 (4) | 0.051 (4) | 0.011 (3) | 0.026 (4) | 0.008 (3) |
O23 | 0.053 (12) | 0.050 (12) | 0.054 (14) | 0.018 (9) | 0.017 (11) | −0.002 (10) |
O24 | 0.067 (15) | 0.039 (12) | 0.054 (12) | −0.013 (10) | 0.015 (12) | 0.015 (10) |
O31 | 0.046 (3) | 0.066 (4) | 0.084 (4) | −0.006 (2) | 0.023 (3) | 0.019 (3) |
O32 | 0.046 (3) | 0.066 (4) | 0.084 (4) | −0.006 (2) | 0.023 (3) | 0.019 (3) |
O41 | 0.0441 (19) | 0.0314 (18) | 0.060 (2) | −0.0005 (15) | 0.0332 (17) | 0.0008 (16) |
O42 | 0.062 (2) | 0.0319 (19) | 0.055 (2) | 0.0017 (16) | 0.0406 (18) | 0.0050 (16) |
O51 | 0.0428 (19) | 0.040 (2) | 0.053 (2) | 0.0024 (16) | 0.0236 (16) | 0.0053 (16) |
O52 | 0.062 (2) | 0.044 (2) | 0.050 (2) | −0.0047 (18) | 0.0307 (18) | 0.0026 (17) |
N1 | 0.0267 (18) | 0.034 (2) | 0.0260 (18) | −0.0024 (16) | 0.0076 (14) | 0.0065 (15) |
N2 | 0.0246 (18) | 0.033 (2) | 0.0324 (19) | −0.0004 (15) | 0.0087 (15) | 0.0069 (16) |
N3 | 0.0224 (17) | 0.032 (2) | 0.0316 (18) | 0.0030 (15) | 0.0143 (14) | 0.0028 (15) |
N4 | 0.0268 (18) | 0.031 (2) | 0.0245 (17) | 0.0013 (15) | 0.0114 (14) | −0.0026 (15) |
N5 | 0.0201 (16) | 0.0252 (18) | 0.0246 (17) | −0.0034 (14) | 0.0096 (13) | −0.0016 (14) |
N6 | 0.0235 (17) | 0.0241 (18) | 0.0271 (17) | 0.0006 (14) | 0.0123 (14) | 0.0058 (14) |
C11 | 0.0234 (19) | 0.024 (2) | 0.0248 (19) | −0.0030 (16) | 0.0097 (16) | −0.0010 (16) |
C12 | 0.0208 (19) | 0.031 (2) | 0.025 (2) | −0.0072 (17) | 0.0096 (16) | −0.0005 (17) |
C13 | 0.026 (2) | 0.039 (3) | 0.027 (2) | −0.0044 (19) | 0.0112 (17) | −0.0007 (18) |
C14 | 0.039 (2) | 0.046 (3) | 0.031 (2) | −0.012 (2) | 0.017 (2) | −0.003 (2) |
C15 | 0.043 (3) | 0.050 (3) | 0.024 (2) | −0.013 (2) | 0.007 (2) | 0.004 (2) |
C16 | 0.033 (2) | 0.045 (3) | 0.029 (2) | −0.003 (2) | 0.0070 (19) | 0.008 (2) |
C21 | 0.0216 (19) | 0.026 (2) | 0.025 (2) | 0.0003 (17) | 0.0082 (16) | 0.0015 (17) |
C22 | 0.023 (2) | 0.037 (3) | 0.024 (2) | −0.0014 (18) | 0.0079 (16) | 0.0115 (19) |
C23 | 0.024 (2) | 0.051 (3) | 0.026 (2) | 0.006 (2) | 0.0129 (17) | 0.011 (2) |
C24 | 0.026 (2) | 0.051 (3) | 0.040 (2) | 0.010 (2) | 0.017 (2) | 0.020 (2) |
C25 | 0.019 (2) | 0.063 (4) | 0.047 (3) | 0.004 (2) | 0.009 (2) | 0.019 (3) |
C26 | 0.028 (2) | 0.041 (3) | 0.039 (2) | −0.009 (2) | 0.0039 (19) | 0.008 (2) |
C31 | 0.0243 (19) | 0.0136 (19) | 0.0240 (19) | −0.0047 (15) | 0.0121 (16) | −0.0011 (15) |
C32 | 0.0224 (19) | 0.024 (2) | 0.0203 (18) | −0.0004 (16) | 0.0112 (15) | −0.0025 (16) |
C33 | 0.025 (2) | 0.029 (2) | 0.0189 (18) | −0.0030 (17) | 0.0103 (16) | −0.0022 (16) |
C34 | 0.0204 (19) | 0.040 (3) | 0.026 (2) | −0.0063 (18) | 0.0105 (16) | −0.0057 (19) |
C35 | 0.018 (2) | 0.054 (3) | 0.036 (2) | 0.006 (2) | 0.0076 (18) | 0.002 (2) |
C36 | 0.027 (2) | 0.041 (3) | 0.039 (2) | 0.007 (2) | 0.0141 (19) | 0.008 (2) |
C41 | 0.0215 (19) | 0.019 (2) | 0.027 (2) | −0.0008 (16) | 0.0120 (16) | 0.0035 (16) |
C42 | 0.0221 (19) | 0.028 (2) | 0.027 (2) | 0.0058 (17) | 0.0122 (16) | 0.0016 (17) |
C43 | 0.022 (2) | 0.040 (3) | 0.030 (2) | 0.0027 (18) | 0.0144 (17) | 0.0044 (19) |
C44 | 0.033 (2) | 0.044 (3) | 0.031 (2) | 0.006 (2) | 0.0208 (19) | 0.009 (2) |
C45 | 0.044 (3) | 0.049 (3) | 0.023 (2) | 0.012 (2) | 0.0183 (19) | 0.001 (2) |
C46 | 0.035 (2) | 0.038 (3) | 0.024 (2) | 0.001 (2) | 0.0107 (18) | −0.0081 (19) |
Geometric parameters (Å, º) top
O11—H11 | 0.8000 | C12—C13 | 1.392 (6) |
O12—H12 | 0.8001 | C13—C14 | 1.387 (6) |
O13—H13 | 0.8000 | C13—H13A | 0.9500 |
O14—H14 | 0.7999 | C14—C15 | 1.386 (7) |
O21—O22 | 1.467 (12) | C14—H14A | 0.9500 |
O21—H21 | 0.8000 | C15—C16 | 1.383 (7) |
O22—H22 | 0.8002 | C15—H15A | 0.9500 |
O23—O24 | 1.44 (4) | C16—H16A | 0.9500 |
O23—H23 | 0.8001 | C21—C22 | 1.491 (5) |
O24—H24 | 0.7998 | C22—C23 | 1.384 (6) |
O31—O31i | 1.465 (9) | C23—C24 | 1.386 (6) |
O31—H31 | 0.7999 | C23—H23A | 0.9500 |
O31—H32 | 0.8813 | C24—C25 | 1.378 (7) |
O32—O32i | 1.463 (13) | C24—H24A | 0.9500 |
O32—H32 | 0.7999 | C25—C26 | 1.389 (7) |
O41—O42 | 1.486 (4) | C25—H25A | 0.9500 |
O41—H41 | 0.7997 | C26—H26A | 0.9500 |
O42—H42 | 0.8001 | C31—C41 | 1.415 (5) |
O51—O52 | 1.485 (5) | C31—C32 | 1.489 (5) |
O51—H51 | 0.8002 | C32—C33 | 1.382 (5) |
O52—H52 | 0.8001 | C33—C34 | 1.377 (5) |
O61—O61ii | 1.471 (10) | C33—H33A | 0.9500 |
O61—H61 | 0.7999 | C34—C35 | 1.391 (6) |
N1—C16 | 1.340 (5) | C34—H34A | 0.9500 |
N1—C12 | 1.345 (5) | C35—C36 | 1.387 (6) |
N2—C26 | 1.340 (5) | C35—H35A | 0.9500 |
N2—C22 | 1.354 (6) | C36—H36A | 0.9500 |
N3—C36 | 1.338 (5) | C41—C42 | 1.483 (5) |
N3—C32 | 1.353 (5) | C42—C43 | 1.394 (6) |
N4—C46 | 1.345 (5) | C43—C44 | 1.381 (6) |
N4—C42 | 1.352 (5) | C43—H43A | 0.9500 |
N5—C31 | 1.336 (5) | C44—C45 | 1.383 (6) |
N5—C11 | 1.342 (5) | C44—H44A | 0.9500 |
N6—C41 | 1.335 (5) | C45—C46 | 1.391 (6) |
N6—C21 | 1.337 (5) | C45—H45A | 0.9500 |
C11—C21 | 1.416 (5) | C46—H46A | 0.9500 |
C11—C12 | 1.493 (5) | | |
| | | |
O12—O11—H11 | 100.6 | C22—C23—C24 | 118.6 (4) |
O11—O12—H12 | 110.1 | C22—C23—H23A | 120.7 |
H12—O12—H14 | 128.2 | C24—C23—H23A | 120.7 |
H13—O12—H14 | 107.7 | C25—C24—C23 | 118.8 (4) |
O14—O13—H13 | 99.5 | C25—C24—H24A | 120.6 |
H11—O14—H12 | 115.4 | C23—C24—H24A | 120.6 |
O13—O14—H14 | 97.8 | C24—C25—C26 | 119.2 (4) |
O22—O21—H21 | 104.0 | C24—C25—H25A | 120.4 |
O21—O22—H22 | 100.4 | C26—C25—H25A | 120.4 |
O24—O23—H23 | 110.2 | N2—C26—C25 | 122.9 (5) |
O23—O24—H24 | 119.8 | N2—C26—H26A | 118.5 |
O31i—O31—H31 | 99.7 | C25—C26—H26A | 118.5 |
O32i—O32—H32 | 78.8 | N5—C31—C41 | 120.5 (3) |
O42—O41—H41 | 93.7 | N5—C31—C32 | 116.0 (3) |
O41—O42—H42 | 97.0 | C41—C31—C32 | 123.5 (3) |
O52—O51—H51 | 92.9 | N3—C32—C33 | 122.5 (4) |
O51—O52—H52 | 93.7 | N3—C32—C31 | 116.9 (3) |
O61ii—O61—H61 | 102.7 | C33—C32—C31 | 120.6 (3) |
C16—N1—C12 | 117.7 (4) | C34—C33—C32 | 119.6 (4) |
C26—N2—C22 | 117.1 (4) | C34—C33—H33A | 120.2 |
C36—N3—C32 | 117.5 (4) | C32—C33—H33A | 120.2 |
C46—N4—C42 | 117.5 (4) | C33—C34—C35 | 118.4 (4) |
C31—N5—C11 | 118.6 (3) | C33—C34—H34A | 120.8 |
C41—N6—C21 | 118.5 (3) | C35—C34—H34A | 120.8 |
N5—C11—C21 | 120.2 (3) | C36—C35—C34 | 118.8 (4) |
N5—C11—C12 | 116.4 (3) | C36—C35—H35A | 120.6 |
C21—C11—C12 | 123.4 (3) | C34—C35—H35A | 120.6 |
N1—C12—C13 | 122.6 (4) | N3—C36—C35 | 123.2 (4) |
N1—C12—C11 | 117.4 (4) | N3—C36—H36A | 118.4 |
C13—C12—C11 | 120.0 (4) | C35—C36—H36A | 118.4 |
C14—C13—C12 | 118.6 (4) | N6—C41—C31 | 120.7 (3) |
C14—C13—H13A | 120.7 | N6—C41—C42 | 116.3 (3) |
C12—C13—H13A | 120.7 | C31—C41—C42 | 122.9 (3) |
C15—C14—C13 | 119.2 (4) | N4—C42—C43 | 122.6 (4) |
C15—C14—H14A | 120.4 | N4—C42—C41 | 116.4 (3) |
C13—C14—H14A | 120.4 | C43—C42—C41 | 121.0 (4) |
C16—C15—C14 | 118.3 (4) | C44—C43—C42 | 119.1 (4) |
C16—C15—H15A | 120.9 | C44—C43—H43A | 120.5 |
C14—C15—H15A | 120.9 | C42—C43—H43A | 120.5 |
N1—C16—C15 | 123.6 (4) | C43—C44—C45 | 118.8 (4) |
N1—C16—H16A | 118.2 | C43—C44—H44A | 120.6 |
C15—C16—H16A | 118.2 | C45—C44—H44A | 120.6 |
N6—C21—C11 | 120.6 (3) | C44—C45—C46 | 119.0 (4) |
N6—C21—C22 | 115.8 (3) | C44—C45—H45A | 120.5 |
C11—C21—C22 | 123.5 (3) | C46—C45—H45A | 120.5 |
N2—C22—C23 | 123.3 (4) | N4—C46—C45 | 123.0 (4) |
N2—C22—C21 | 116.0 (4) | N4—C46—H46A | 118.5 |
C23—C22—C21 | 120.6 (4) | C45—C46—H46A | 118.5 |
| | | |
C31—N5—C11—C21 | 3.9 (6) | C41—C31—C32—N3 | −47.1 (5) |
C31—N5—C11—C12 | −177.8 (4) | N5—C31—C32—C33 | −45.2 (5) |
C16—N1—C12—C13 | −3.0 (6) | C41—C31—C32—C33 | 135.2 (4) |
C16—N1—C12—C11 | 176.3 (4) | N3—C32—C33—C34 | 0.4 (6) |
N5—C11—C12—N1 | 140.0 (4) | C31—C32—C33—C34 | 178.0 (3) |
C21—C11—C12—N1 | −41.8 (6) | C32—C33—C34—C35 | −0.1 (6) |
N5—C11—C12—C13 | −40.7 (6) | C33—C34—C35—C36 | 0.0 (6) |
C21—C11—C12—C13 | 137.6 (4) | C32—N3—C36—C35 | 0.5 (7) |
N1—C12—C13—C14 | 2.0 (6) | C34—C35—C36—N3 | −0.2 (7) |
C11—C12—C13—C14 | −177.3 (4) | C21—N6—C41—C31 | 3.8 (6) |
C12—C13—C14—C15 | 0.5 (7) | C21—N6—C41—C42 | −175.4 (4) |
C13—C14—C15—C16 | −1.8 (7) | N5—C31—C41—N6 | −8.3 (6) |
C12—N1—C16—C15 | 1.6 (7) | C32—C31—C41—N6 | 171.2 (4) |
C14—C15—C16—N1 | 0.7 (7) | N5—C31—C41—C42 | 170.9 (4) |
C41—N6—C21—C11 | 4.3 (6) | C32—C31—C41—C42 | −9.6 (6) |
C41—N6—C21—C22 | −176.0 (4) | C46—N4—C42—C43 | −2.3 (6) |
N5—C11—C21—N6 | −8.4 (6) | C46—N4—C42—C41 | 179.2 (4) |
C12—C11—C21—N6 | 173.4 (4) | N6—C41—C42—N4 | 135.6 (4) |
N5—C11—C21—C22 | 171.9 (4) | C31—C41—C42—N4 | −43.6 (5) |
C12—C11—C21—C22 | −6.2 (7) | N6—C41—C42—C43 | −42.8 (6) |
C26—N2—C22—C23 | −0.4 (6) | C31—C41—C42—C43 | 137.9 (4) |
C26—N2—C22—C21 | −178.1 (4) | N4—C42—C43—C44 | 1.5 (6) |
N6—C21—C22—N2 | 130.8 (4) | C41—C42—C43—C44 | 179.9 (4) |
C11—C21—C22—N2 | −49.6 (6) | C42—C43—C44—C45 | 0.2 (6) |
N6—C21—C22—C23 | −47.0 (6) | C43—C44—C45—C46 | −1.0 (7) |
C11—C21—C22—C23 | 132.7 (4) | C42—N4—C46—C45 | 1.6 (6) |
N2—C22—C23—C24 | 0.6 (6) | C44—C45—C46—N4 | 0.1 (7) |
C21—C22—C23—C24 | 178.1 (4) | H11—O11—O12—H12 | −116.1 |
C22—C23—C24—C25 | −0.8 (6) | H13—O13—O14—H14 | 127.8 |
C23—C24—C25—C26 | 0.9 (7) | H21—O21—O22—H22 | 125.3 |
C22—N2—C26—C25 | 0.5 (6) | H23—O23—O24—H24 | −118.1 |
C24—C25—C26—N2 | −0.8 (7) | H31—O31—O31i—H31i | 180.0 |
C11—N5—C31—C41 | 4.1 (6) | H32—O32—O32i—H32i | 180.0 |
C11—N5—C31—C32 | −175.5 (4) | H41—O41—O42—H42 | −152.1 |
C36—N3—C32—C33 | −0.6 (6) | H51—O51—O52—H52 | −158.2 |
C36—N3—C32—C31 | −178.3 (4) | H61—O61—O61ii—H61ii | 180.0 |
N5—C31—C32—N3 | 132.5 (4) | | |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O11—H11···O52iii | 0.80 | 1.99 | 2.793 (7) | 179 |
O12—H12···O41iii | 0.80 | 1.99 | 2.789 (7) | 180 |
O13—H13···O41iii | 0.80 | 1.89 | 2.69 (4) | 180 |
O14—H14···O52iii | 0.80 | 2.05 | 2.85 (3) | 179 |
O21—H21···O51 | 0.80 | 2.02 | 2.820 (9) | 180 |
O22—H22···O42 | 0.80 | 2.07 | 2.866 (11) | 180 |
O23—H23···O51 | 0.80 | 1.96 | 2.77 (3) | 180 |
O24—H24···O42 | 0.80 | 1.84 | 2.64 (3) | 180 |
O31—H31···O22 | 0.80 | 2.15 | 2.947 (9) | 176 |
O32—H32···O24 | 0.80 | 2.34 | 3.14 (5) | 173 |
O41—H41···N3 | 0.80 | 1.93 | 2.729 (5) | 180 |
O42—H42···N4iv | 0.80 | 1.97 | 2.770 (5) | 180 |
O51—H51···N2 | 0.80 | 1.94 | 2.737 (5) | 180 |
O52—H52···N1iv | 0.80 | 1.94 | 2.740 (5) | 180 |
O61—H61···O11 | 0.80 | 1.64 | 2.440 (17) | 178 |
Symmetry codes: (iii) x, y−1, z; (iv) x, y+1, z. |