Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033277/cs2014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033277/cs2014Isup2.hkl |
CCDC reference: 624184
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.051
- wR factor = 0.122
- Data-to-parameter ratio = 6.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.39 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 28.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT413_ALERT_2_C Short Inter XH3 .. XHn H27C .. H13A .. 2.10 Ang. PLAT707_ALERT_1_C D...A Calc 3.222(12), Rep 3.207(5), Dev.. 1.25 Sigma C23 -O7 1.555 1.555 PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 40.70 Deg. C13' -C14 -C13 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.60 Deg. C12 -C11 -C12' 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C10 H7 N4 O5
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 25.24 From the CIF: _reflns_number_total 2353 Count of symmetry unique reflns 2365 Completeness (_total/calc) 99.49% 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 PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C15H25N2O+·C10H7N4O5−·0.28H2O | F(000) = 550 |
Mr = 517.61 | Dx = 1.360 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 9133 reflections |
a = 8.3939 (7) Å | θ = 1.7–23.9° |
b = 14.9227 (13) Å | µ = 0.10 mm−1 |
c = 10.0939 (9) Å | T = 273 K |
β = 92.166 (2)° | Block, colourless |
V = 1263.46 (19) Å3 | 0.37 × 0.35 × 0.32 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 2353 independent reflections |
Radiation source: fine-focus sealed tube | 2173 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 25.2°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→10 |
Tmin = 0.955, Tmax = 0.961 | k = −17→17 |
6696 measured reflections | l = −7→12 |
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) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.2261P] where P = (Fo2 + 2Fc2)/3 |
2353 reflections | (Δ/σ)max < 0.001 |
368 parameters | Δρmax = 0.23 e Å−3 |
12 restraints | Δρmin = −0.20 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O7 | 0.6391 (14) | 1.0699 (8) | 0.7971 (11) | 0.085 (3)* | 0.28 |
H7WA | 0.5842 | 1.0890 | 0.7336 | 0.102* | 0.28 |
H7WB | 0.6631 | 1.0168 | 0.7930 | 0.102* | 0.28 |
O1 | 0.6319 (5) | 0.9008 (4) | 0.7790 (3) | 0.1075 (14) | |
O2 | −0.0459 (5) | 1.0693 (4) | 0.9506 (4) | 0.1240 (17) | |
O3 | 0.1687 (5) | 0.9923 (3) | 0.9642 (4) | 0.1060 (13) | |
O4 | 0.4294 (3) | 1.0651 (2) | 0.3344 (3) | 0.0635 (7) | |
O5 | 0.4878 (5) | 1.1169 (3) | 0.0641 (3) | 0.0941 (11) | |
O6 | 0.3083 (5) | 1.1998 (3) | −0.0342 (3) | 0.0957 (11) | |
N16 | 0.5444 (4) | 0.8831 (2) | 0.5684 (3) | 0.0594 (9) | |
N1 | 0.6002 (4) | 0.9256 (2) | 0.2128 (3) | 0.0534 (8) | |
N2 | 0.0754 (5) | 1.0404 (3) | 0.9042 (4) | 0.0827 (12) | |
N3 | 0.2057 (4) | 1.1469 (2) | 0.3863 (3) | 0.0540 (8) | |
N4 | 0.0962 (4) | 1.2065 (3) | 0.3253 (4) | 0.0698 (10) | |
N5 | 0.3625 (5) | 1.1596 (3) | 0.0659 (4) | 0.0762 (11) | |
C15 | 0.5330 (5) | 0.8706 (3) | 0.6996 (4) | 0.0670 (11) | |
C14 | 0.3949 (7) | 0.8176 (4) | 0.7475 (4) | 0.0874 (16) | |
C13' | 0.3173 (10) | 0.7579 (4) | 0.6406 (6) | 0.064 (3) | 0.527 (12) |
H13" | 0.2241 | 0.7271 | 0.6719 | 0.077* | 0.527 (12) |
H13' | 0.3917 | 0.7145 | 0.6070 | 0.077* | 0.527 (12) |
C12' | 0.2731 (7) | 0.8297 (5) | 0.5380 (9) | 0.051 (3) | 0.527 (12) |
H12' | 0.2280 | 0.8812 | 0.5815 | 0.061* | 0.527 (12) |
H12" | 0.1937 | 0.8064 | 0.4748 | 0.061* | 0.527 (12) |
C13 | 0.2532 (9) | 0.8191 (9) | 0.6469 (8) | 0.085 (4) | 0.473 (12) |
H13A | 0.1712 | 0.7792 | 0.6777 | 0.103* | 0.473 (12) |
H13B | 0.2090 | 0.8792 | 0.6438 | 0.103* | 0.473 (12) |
C12 | 0.2946 (14) | 0.7914 (7) | 0.5068 (10) | 0.070 (4) | 0.473 (12) |
H12A | 0.2014 | 0.7947 | 0.4472 | 0.084* | 0.473 (12) |
H12B | 0.3357 | 0.7306 | 0.5061 | 0.084* | 0.473 (12) |
C11 | 0.4222 (4) | 0.8581 (3) | 0.4653 (4) | 0.0585 (10) | |
H11 | 0.3724 | 0.9118 | 0.4264 | 0.070* | |
C7 | 0.5003 (5) | 0.8024 (2) | 0.3581 (5) | 0.0641 (11) | |
H7 | 0.5383 | 0.7471 | 0.4011 | 0.077* | |
C8 | 0.3878 (7) | 0.7742 (4) | 0.2437 (5) | 0.0861 (15) | |
H8A | 0.2922 | 0.7483 | 0.2789 | 0.103* | |
H8B | 0.4390 | 0.7286 | 0.1917 | 0.103* | |
C9 | 0.3417 (6) | 0.8534 (4) | 0.1543 (4) | 0.0818 (14) | |
H9A | 0.2731 | 0.8328 | 0.0811 | 0.098* | |
H9B | 0.2832 | 0.8972 | 0.2043 | 0.098* | |
C10 | 0.4882 (5) | 0.8962 (3) | 0.1016 (4) | 0.0701 (12) | |
H10A | 0.4577 | 0.9476 | 0.0476 | 0.084* | |
H10B | 0.5420 | 0.8537 | 0.0458 | 0.084* | |
C2 | 0.7453 (5) | 0.9684 (3) | 0.1566 (4) | 0.0689 (12) | |
H2A | 0.8009 | 0.9247 | 0.1041 | 0.083* | |
H2B | 0.7129 | 1.0176 | 0.0990 | 0.083* | |
C3 | 0.8552 (5) | 1.0025 (4) | 0.2661 (5) | 0.0760 (13) | |
H3A | 0.8016 | 1.0487 | 0.3152 | 0.091* | |
H3B | 0.9488 | 1.0290 | 0.2283 | 0.091* | |
C4 | 0.9059 (5) | 0.9279 (4) | 0.3590 (5) | 0.0756 (13) | |
H4A | 0.9703 | 0.9525 | 0.4320 | 0.091* | |
H4B | 0.9712 | 0.8856 | 0.3122 | 0.091* | |
C5 | 0.7634 (4) | 0.8786 (3) | 0.4139 (4) | 0.0579 (10) | |
H5 | 0.8051 | 0.8241 | 0.4569 | 0.069* | |
C6 | 0.6469 (5) | 0.8486 (3) | 0.3038 (4) | 0.0584 (10) | |
H6 | 0.7021 | 0.8043 | 0.2504 | 0.070* | |
C17 | 0.6796 (5) | 0.9316 (3) | 0.5192 (4) | 0.0604 (10) | |
H17A | 0.7546 | 0.9443 | 0.5924 | 0.072* | |
H17B | 0.6435 | 0.9883 | 0.4821 | 0.072* | |
C18 | 0.1119 (5) | 1.0677 (3) | 0.7690 (4) | 0.0590 (10) | |
C19 | −0.0077 (5) | 1.1040 (3) | 0.6906 (4) | 0.0661 (11) | |
H19 | −0.1095 | 1.1108 | 0.7224 | 0.079* | |
C20 | 0.0253 (5) | 1.1306 (3) | 0.5632 (4) | 0.0622 (10) | |
H20 | −0.0543 | 1.1564 | 0.5091 | 0.075* | |
C21 | 0.1766 (4) | 1.1187 (2) | 0.5161 (3) | 0.0479 (8) | |
C22 | 0.2953 (5) | 1.0822 (3) | 0.5978 (4) | 0.0521 (9) | |
H22 | 0.3975 | 1.0748 | 0.5669 | 0.063* | |
C23 | 0.2627 (5) | 1.0568 (3) | 0.7248 (4) | 0.0598 (10) | |
H23 | 0.3424 | 1.0324 | 0.7802 | 0.072* | |
C24 | 0.1419 (5) | 1.2165 (3) | 0.2043 (4) | 0.0722 (12) | |
C25 | 0.2796 (5) | 1.1645 (3) | 0.1825 (4) | 0.0628 (10) | |
C26 | 0.3213 (5) | 1.1186 (3) | 0.3011 (4) | 0.0522 (9) | |
C27 | 0.0540 (7) | 1.2792 (5) | 0.1141 (6) | 0.110 (2) | |
H27A | 0.0075 | 1.2465 | 0.0404 | 0.165* | |
H27B | 0.1263 | 1.3235 | 0.0823 | 0.165* | |
H27C | −0.0287 | 1.3083 | 0.1612 | 0.165* | |
H14A | 0.335 (6) | 0.855 (4) | 0.806 (5) | 0.132* | |
H14B | 0.438 (7) | 0.771 (3) | 0.805 (5) | 0.132* | |
H1 | 0.550 (4) | 0.967 (3) | 0.259 (4) | 0.044 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.109 (3) | 0.163 (4) | 0.0505 (19) | −0.028 (3) | −0.0012 (18) | −0.008 (2) |
O2 | 0.107 (3) | 0.192 (5) | 0.076 (2) | 0.004 (3) | 0.040 (2) | 0.030 (3) |
O3 | 0.127 (3) | 0.128 (3) | 0.063 (2) | 0.001 (3) | −0.001 (2) | 0.041 (2) |
O4 | 0.0790 (18) | 0.0594 (16) | 0.0530 (15) | 0.0160 (16) | 0.0150 (13) | 0.0039 (14) |
O5 | 0.110 (3) | 0.104 (3) | 0.070 (2) | 0.019 (2) | 0.0365 (19) | 0.007 (2) |
O6 | 0.140 (3) | 0.096 (3) | 0.0513 (17) | −0.006 (2) | 0.0097 (19) | 0.0286 (18) |
N16 | 0.0560 (18) | 0.075 (2) | 0.0473 (18) | −0.0043 (17) | 0.0001 (14) | 0.0139 (16) |
N1 | 0.0657 (19) | 0.0539 (18) | 0.0415 (16) | 0.0002 (16) | 0.0114 (14) | −0.0031 (14) |
N2 | 0.093 (3) | 0.103 (3) | 0.052 (2) | −0.014 (3) | 0.007 (2) | 0.018 (2) |
N3 | 0.0643 (18) | 0.0509 (17) | 0.0473 (16) | 0.0098 (15) | 0.0065 (14) | 0.0117 (14) |
N4 | 0.073 (2) | 0.071 (2) | 0.065 (2) | 0.0140 (19) | 0.0064 (18) | 0.0268 (19) |
N5 | 0.108 (3) | 0.067 (2) | 0.054 (2) | −0.011 (2) | 0.017 (2) | 0.0071 (19) |
C15 | 0.074 (3) | 0.076 (3) | 0.051 (2) | 0.008 (2) | 0.009 (2) | 0.005 (2) |
C14 | 0.097 (4) | 0.111 (4) | 0.056 (3) | −0.005 (3) | 0.016 (3) | 0.014 (3) |
C13' | 0.076 (5) | 0.042 (4) | 0.076 (6) | 0.008 (4) | 0.026 (4) | 0.009 (4) |
C12' | 0.053 (4) | 0.048 (5) | 0.050 (6) | 0.005 (4) | −0.009 (4) | −0.004 (4) |
C13 | 0.097 (8) | 0.093 (9) | 0.068 (8) | −0.024 (7) | 0.022 (6) | −0.004 (6) |
C12 | 0.084 (7) | 0.064 (8) | 0.062 (7) | −0.021 (6) | 0.015 (5) | −0.004 (6) |
C11 | 0.055 (2) | 0.068 (2) | 0.052 (2) | −0.0039 (19) | −0.0014 (17) | 0.023 (2) |
C7 | 0.079 (3) | 0.041 (2) | 0.072 (3) | −0.0062 (19) | −0.006 (2) | 0.0082 (19) |
C8 | 0.104 (4) | 0.072 (3) | 0.081 (3) | −0.029 (3) | −0.005 (3) | −0.008 (3) |
C9 | 0.090 (3) | 0.099 (4) | 0.055 (3) | −0.025 (3) | −0.015 (2) | −0.003 (3) |
C10 | 0.086 (3) | 0.082 (3) | 0.043 (2) | −0.004 (2) | −0.003 (2) | −0.005 (2) |
C2 | 0.071 (3) | 0.082 (3) | 0.055 (2) | −0.003 (2) | 0.021 (2) | 0.002 (2) |
C3 | 0.065 (3) | 0.090 (3) | 0.074 (3) | −0.019 (2) | 0.020 (2) | 0.006 (3) |
C4 | 0.057 (2) | 0.091 (3) | 0.080 (3) | 0.003 (2) | 0.008 (2) | −0.003 (3) |
C5 | 0.052 (2) | 0.058 (2) | 0.063 (2) | 0.0081 (18) | 0.0007 (18) | 0.009 (2) |
C6 | 0.068 (2) | 0.0423 (19) | 0.065 (2) | 0.0051 (18) | 0.007 (2) | −0.0019 (18) |
C17 | 0.060 (2) | 0.071 (3) | 0.050 (2) | −0.007 (2) | −0.0028 (18) | 0.004 (2) |
C18 | 0.073 (2) | 0.059 (2) | 0.045 (2) | −0.006 (2) | 0.0076 (18) | 0.0045 (18) |
C19 | 0.063 (2) | 0.077 (3) | 0.060 (2) | 0.004 (2) | 0.015 (2) | 0.006 (2) |
C20 | 0.062 (2) | 0.066 (2) | 0.058 (2) | 0.013 (2) | 0.0019 (18) | 0.014 (2) |
C21 | 0.057 (2) | 0.0401 (17) | 0.047 (2) | 0.0023 (16) | 0.0051 (16) | 0.0005 (16) |
C22 | 0.058 (2) | 0.0504 (19) | 0.048 (2) | 0.0028 (17) | 0.0052 (16) | 0.0015 (16) |
C23 | 0.068 (2) | 0.060 (2) | 0.051 (2) | 0.004 (2) | −0.0035 (18) | 0.006 (2) |
C24 | 0.080 (3) | 0.074 (3) | 0.063 (3) | 0.002 (2) | 0.003 (2) | 0.030 (2) |
C25 | 0.080 (3) | 0.058 (2) | 0.051 (2) | −0.005 (2) | 0.011 (2) | 0.0129 (19) |
C26 | 0.065 (2) | 0.0426 (19) | 0.050 (2) | −0.0038 (19) | 0.0058 (17) | 0.0039 (17) |
C27 | 0.111 (4) | 0.128 (5) | 0.091 (4) | 0.033 (4) | 0.014 (3) | 0.057 (4) |
O7—H7WA | 0.8253 | C7—C6 | 1.530 (6) |
O7—H7WB | 0.8199 | C7—H7 | 0.9800 |
O1—C15 | 1.219 (6) | C8—C9 | 1.528 (8) |
O2—N2 | 1.216 (6) | C8—H8A | 0.9700 |
O3—N2 | 1.208 (5) | C8—H8B | 0.9700 |
O4—C26 | 1.245 (4) | C9—C10 | 1.501 (6) |
O5—N5 | 1.230 (5) | C9—H9A | 0.9700 |
O6—N5 | 1.246 (5) | C9—H9B | 0.9700 |
N16—C15 | 1.344 (5) | C10—H10A | 0.9700 |
N16—C17 | 1.449 (5) | C10—H10B | 0.9700 |
N16—C11 | 1.481 (5) | C2—C3 | 1.501 (7) |
N1—C10 | 1.503 (5) | C2—H2A | 0.9700 |
N1—C2 | 1.505 (5) | C2—H2B | 0.9700 |
N1—C6 | 1.513 (5) | C3—C4 | 1.506 (7) |
N1—H1 | 0.89 (4) | C3—H3A | 0.9700 |
N2—C18 | 1.468 (5) | C3—H3B | 0.9700 |
N3—C26 | 1.387 (5) | C4—C5 | 1.526 (6) |
N3—N4 | 1.405 (4) | C4—H4A | 0.9700 |
N3—C21 | 1.406 (4) | C4—H4B | 0.9700 |
N4—C24 | 1.303 (5) | C5—C17 | 1.519 (6) |
N5—C25 | 1.392 (5) | C5—C6 | 1.519 (6) |
C15—C14 | 1.498 (7) | C5—H5 | 0.9800 |
C14—C13' | 1.526 (3) | C6—H6 | 0.9800 |
C14—C13 | 1.535 (3) | C17—H17A | 0.9700 |
C14—H14A | 0.97 (4) | C17—H17B | 0.9700 |
C14—H14B | 0.97 (4) | C18—C19 | 1.366 (6) |
C13'—C12' | 1.527 (3) | C18—C23 | 1.368 (6) |
C13'—H13" | 0.9700 | C19—C20 | 1.384 (6) |
C13'—H13' | 0.9700 | C19—H19 | 0.9300 |
C12'—C11 | 1.534 (3) | C20—C21 | 1.384 (5) |
C12'—H12' | 0.9700 | C20—H20 | 0.9300 |
C12'—H12" | 0.9700 | C21—C22 | 1.382 (5) |
C13—C12 | 1.526 (3) | C22—C23 | 1.374 (5) |
C13—H13A | 0.9700 | C22—H22 | 0.9300 |
C13—H13B | 0.9700 | C23—H23 | 0.9300 |
C12—C11 | 1.532 (3) | C24—C25 | 1.417 (6) |
C12—H12A | 0.9700 | C24—C27 | 1.482 (7) |
C12—H12B | 0.9700 | C25—C26 | 1.411 (6) |
C11—C7 | 1.530 (6) | C27—H27A | 0.9600 |
C11—H11 | 0.9800 | C27—H27B | 0.9600 |
C7—C8 | 1.523 (6) | C27—H27C | 0.9600 |
H7WA—O7—H7WB | 115.2 | C10—C9—H9A | 109.6 |
C15—N16—C17 | 119.5 (3) | C8—C9—H9A | 109.6 |
C15—N16—C11 | 125.7 (3) | C10—C9—H9B | 109.6 |
C17—N16—C11 | 114.6 (3) | C8—C9—H9B | 109.6 |
C10—N1—C2 | 109.5 (3) | H9A—C9—H9B | 108.1 |
C10—N1—C6 | 111.8 (3) | C9—C10—N1 | 110.9 (3) |
C2—N1—C6 | 110.8 (3) | C9—C10—H10A | 109.5 |
C10—N1—H1 | 107 (2) | N1—C10—H10A | 109.5 |
C2—N1—H1 | 108 (2) | C9—C10—H10B | 109.5 |
C6—N1—H1 | 109 (2) | N1—C10—H10B | 109.5 |
O3—N2—O2 | 123.7 (4) | H10A—C10—H10B | 108.0 |
O3—N2—C18 | 118.5 (4) | C3—C2—N1 | 110.5 (3) |
O2—N2—C18 | 117.8 (4) | C3—C2—H2A | 109.6 |
C26—N3—N4 | 112.5 (3) | N1—C2—H2A | 109.6 |
C26—N3—C21 | 129.5 (3) | C3—C2—H2B | 109.6 |
N4—N3—C21 | 117.7 (3) | N1—C2—H2B | 109.6 |
C24—N4—N3 | 105.8 (3) | H2A—C2—H2B | 108.1 |
O5—N5—O6 | 121.6 (4) | C2—C3—C4 | 111.0 (4) |
O5—N5—C25 | 119.6 (4) | C2—C3—H3A | 109.4 |
O6—N5—C25 | 118.8 (4) | C4—C3—H3A | 109.4 |
O1—C15—N16 | 121.6 (4) | C2—C3—H3B | 109.4 |
O1—C15—C14 | 119.9 (4) | C4—C3—H3B | 109.4 |
N16—C15—C14 | 118.5 (4) | H3A—C3—H3B | 108.0 |
C15—C14—C13' | 113.2 (4) | C3—C4—C5 | 112.1 (3) |
C15—C14—C13 | 111.6 (5) | C3—C4—H4A | 109.2 |
C13'—C14—C13 | 40.7 (5) | C5—C4—H4A | 109.2 |
C15—C14—H14A | 108 (4) | C3—C4—H4B | 109.2 |
C13'—C14—H14A | 124 (4) | C5—C4—H4B | 109.2 |
C13—C14—H14A | 89 (4) | H4A—C4—H4B | 107.9 |
C15—C14—H14B | 107 (4) | C17—C5—C6 | 111.3 (3) |
C13'—C14—H14B | 98 (4) | C17—C5—C4 | 113.1 (4) |
C13—C14—H14B | 132 (4) | C6—C5—C4 | 111.6 (3) |
H14A—C14—H14B | 104 (5) | C17—C5—H5 | 106.8 |
C14—C13'—C12' | 99.0 (6) | C6—C5—H5 | 106.8 |
C14—C13'—H13" | 112.0 | C4—C5—H5 | 106.8 |
C12'—C13'—H13" | 112.0 | N1—C6—C5 | 111.4 (3) |
C14—C13'—H13' | 112.0 | N1—C6—C7 | 111.5 (3) |
C12'—C13'—H13' | 112.0 | C5—C6—C7 | 112.0 (3) |
H13"—C13'—H13' | 109.7 | N1—C6—H6 | 107.2 |
C13'—C12'—C11 | 109.7 (5) | C5—C6—H6 | 107.2 |
C13'—C12'—H12' | 109.7 | C7—C6—H6 | 107.2 |
C11—C12'—H12' | 109.7 | N16—C17—C5 | 111.6 (3) |
C13'—C12'—H12" | 109.7 | N16—C17—H17A | 109.3 |
C11—C12'—H12" | 109.7 | C5—C17—H17A | 109.3 |
H12'—C12'—H12" | 108.2 | N16—C17—H17B | 109.3 |
C12—C13—C14 | 114.3 (8) | C5—C17—H17B | 109.3 |
C12—C13—H13A | 108.7 | H17A—C17—H17B | 108.0 |
C14—C13—H13A | 108.7 | C19—C18—C23 | 121.8 (4) |
C12—C13—H13B | 108.7 | C19—C18—N2 | 118.3 (4) |
C14—C13—H13B | 108.7 | C23—C18—N2 | 119.9 (4) |
H13A—C13—H13B | 107.6 | C18—C19—C20 | 118.9 (4) |
C13—C12—C11 | 105.3 (7) | C18—C19—H19 | 120.5 |
C13—C12—H12A | 110.7 | C20—C19—H19 | 120.5 |
C11—C12—H12A | 110.7 | C21—C20—C19 | 120.1 (4) |
C13—C12—H12B | 110.7 | C21—C20—H20 | 120.0 |
C11—C12—H12B | 110.7 | C19—C20—H20 | 120.0 |
H12A—C12—H12B | 108.8 | C22—C21—C20 | 119.7 (3) |
N16—C11—C7 | 109.3 (3) | C22—C21—N3 | 121.9 (3) |
N16—C11—C12 | 116.4 (5) | C20—C21—N3 | 118.4 (3) |
C7—C11—C12 | 99.4 (5) | C23—C22—C21 | 120.1 (4) |
N16—C11—C12' | 106.8 (4) | C23—C22—H22 | 120.0 |
C7—C11—C12' | 124.6 (5) | C21—C22—H22 | 120.0 |
C12—C11—C12' | 25.6 (4) | C18—C23—C22 | 119.4 (4) |
N16—C11—H11 | 110.4 | C18—C23—H23 | 120.3 |
C7—C11—H11 | 110.4 | C22—C23—H23 | 120.3 |
C12—C11—H11 | 110.4 | N4—C24—C25 | 110.7 (4) |
C12'—C11—H11 | 94.2 | N4—C24—C27 | 119.4 (5) |
C8—C7—C6 | 109.7 (4) | C25—C24—C27 | 129.9 (4) |
C8—C7—C11 | 114.6 (4) | N5—C25—C26 | 125.2 (4) |
C6—C7—C11 | 112.4 (3) | N5—C25—C24 | 126.6 (4) |
C8—C7—H7 | 106.6 | C26—C25—C24 | 108.2 (4) |
C6—C7—H7 | 106.6 | O4—C26—N3 | 123.2 (3) |
C11—C7—H7 | 106.6 | O4—C26—C25 | 134.0 (4) |
C7—C8—C9 | 111.7 (4) | N3—C26—C25 | 102.7 (3) |
C7—C8—H8A | 109.3 | C24—C27—H27A | 109.5 |
C9—C8—H8A | 109.3 | C24—C27—H27B | 109.5 |
C7—C8—H8B | 109.3 | H27A—C27—H27B | 109.5 |
C9—C8—H8B | 109.3 | C24—C27—H27C | 109.5 |
H8A—C8—H8B | 107.9 | H27A—C27—H27C | 109.5 |
C10—C9—C8 | 110.2 (4) | H27B—C27—H27C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
07—H7WA···O1 | 0.83 (2) | 1.95 (2) | 2.832 (5) | 171 (4) |
N1—H1···O4 | 0.89 (4) | 1.95 (4) | 2.832 (5) | 171 (4) |
C2—H2B···O5 | 0.97 | 2.42 | 3.209 (6) | 139 |
C8—H8B···O7i | 0.97 | 2.47 | 3.088 (6) | 121 |
C10—H10A···O5 | 0.97 | 2.55 | 3.317 (7) | 136 |
C11—H11···O4 | 0.98 | 2.52 | 3.362 (5) | 144 |
C13—H13A···N4ii | 0.97 | 2.50 | 3.404 (6) | 156 |
C17—H17B···O4 | 0.97 | 2.56 | 3.401 (5) | 145 |
C19—H19···O7iii | 0.93 | 2.35 | 3.237 (6) | 158 |
C23—H23···O7 | 0.93 | 2.54 | 3.207 (5) | 129 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x, y−1/2, −z+1; (iii) x−1, y, z. |
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