Two molecules of the title compound, C10H16N2O3, constitute the asymmetric unit. The molecules form a two-dimensional hydrogen-bonded sheet in the ab plane.
Supporting information
CCDC reference: 259614
Key indicators
- Single-crystal X-ray study
- T = 163 K
- Mean (C-C) = 0.005 Å
- R factor = 0.077
- wR factor = 0.198
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.587 1.000
Tmin' and Tmax expected: 0.937 0.991
RR' = 0.621
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.62
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 0.605
Test value = 0.600
DIFMX02_ALERT_1_C The minimum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.61 e/A 3
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
6-Isopropoxy-5-isopropylpyrimidine-2,4(1
H,3H)-dione
top
Crystal data top
C10H16N2O3 | Z = 4 |
Mr = 212.25 | F(000) = 456 |
Triclinic, P1 | Dx = 1.254 Mg m−3 |
Hall symbol: -P 1 | Melting point: 501 K |
a = 8.769 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.178 (8) Å | Cell parameters from 2889 reflections |
c = 12.418 (9) Å | θ = 4.8–52.0° |
α = 71.074 (9)° | µ = 0.09 mm−1 |
β = 77.684 (9)° | T = 163 K |
γ = 88.014 (9)° | Needle, colourless |
V = 1124.1 (13) Å3 | 0.70 × 0.10 × 0.10 mm |
Data collection top
Bruker SMART CCD diffractometer | 4703 independent reflections |
Radiation source: fine-focus sealed tube | 2497 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 8.192 pixels mm-1 | θmax = 27.5°, θmin = 2.2° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | k = −7→14 |
Tmin = 0.587, Tmax = 1.000 | l = −16→15 |
14452 measured reflections | |
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)] = 0.077 | H-atom parameters constrained |
wR(F2) = 0.198 | w = 1/[σ2(Fo2) + (0.1178P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max < 0.001 |
4703 reflections | Δρmax = 0.61 e Å−3 |
280 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.032 (5) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.6073 (3) | 0.7615 (2) | 0.12465 (19) | 0.0259 (6) | |
H1A | 0.5443 | 0.7030 | 0.1227 | 0.031* | |
C2 | 0.7496 (3) | 0.7875 (3) | 0.0468 (2) | 0.0261 (7) | |
O2 | 0.7881 (2) | 0.73286 (19) | −0.02646 (17) | 0.0323 (5) | |
N3 | 0.8405 (3) | 0.8774 (2) | 0.0565 (2) | 0.0267 (6) | |
H3A | 0.9331 | 0.8947 | 0.0094 | 0.032* | |
C4 | 0.7998 (3) | 0.9451 (3) | 0.1348 (2) | 0.0261 (7) | |
O4 | 0.8924 (2) | 1.02879 (19) | 0.12908 (17) | 0.0330 (5) | |
C5 | 0.6491 (3) | 0.9141 (2) | 0.2140 (2) | 0.0245 (7) | |
C6 | 0.5595 (3) | 0.8228 (3) | 0.2051 (2) | 0.0245 (7) | |
O6 | 0.4186 (2) | 0.78599 (18) | 0.27840 (16) | 0.0283 (5) | |
C7 | 0.5918 (4) | 0.9834 (3) | 0.3016 (3) | 0.0359 (8) | |
H7A | 0.4859 | 0.9461 | 0.3463 | 0.043* | |
C8 | 0.5718 (5) | 1.1240 (3) | 0.2388 (4) | 0.0568 (11) | |
H8A | 0.5037 | 1.1322 | 0.1838 | 0.085* | |
H8B | 0.6741 | 1.1647 | 0.1963 | 0.085* | |
H8C | 0.5249 | 1.1650 | 0.2962 | 0.085* | |
C9 | 0.6960 (4) | 0.9629 (4) | 0.3897 (3) | 0.0572 (11) | |
H9A | 0.7003 | 0.8721 | 0.4305 | 0.086* | |
H9B | 0.6530 | 1.0059 | 0.4463 | 0.086* | |
H9C | 0.8015 | 0.9975 | 0.3489 | 0.086* | |
C10 | 0.2868 (3) | 0.7628 (3) | 0.2300 (3) | 0.0287 (7) | |
H10A | 0.3090 | 0.6893 | 0.2005 | 0.034* | |
C11 | 0.2616 (4) | 0.8789 (3) | 0.1315 (3) | 0.0427 (9) | |
H11A | 0.3562 | 0.8992 | 0.0694 | 0.064* | |
H11B | 0.2386 | 0.9505 | 0.1607 | 0.064* | |
H11C | 0.1737 | 0.8620 | 0.1005 | 0.064* | |
C12 | 0.1486 (4) | 0.7296 (3) | 0.3315 (3) | 0.0436 (9) | |
H12A | 0.1722 | 0.6565 | 0.3942 | 0.065* | |
H12B | 0.0572 | 0.7087 | 0.3065 | 0.065* | |
H12C | 0.1266 | 0.8019 | 0.3599 | 0.065* | |
N1' | 0.9181 (3) | 0.3592 (2) | 0.0980 (2) | 0.0266 (6) | |
H1D | 1.0097 | 0.3248 | 0.0894 | 0.032* | |
C2' | 0.8376 (3) | 0.3844 (3) | 0.0087 (2) | 0.0268 (7) | |
O2' | 0.8916 (2) | 0.3626 (2) | −0.08229 (17) | 0.0355 (6) | |
N3' | 0.6948 (3) | 0.4372 (2) | 0.0306 (2) | 0.0261 (6) | |
H3D | 0.6385 | 0.4516 | −0.0228 | 0.031* | |
C4' | 0.6317 (3) | 0.4698 (3) | 0.1293 (2) | 0.0251 (7) | |
O4' | 0.5010 (2) | 0.52323 (18) | 0.13321 (16) | 0.0279 (5) | |
C5' | 0.7186 (3) | 0.4424 (2) | 0.2188 (2) | 0.0238 (7) | |
C6' | 0.8604 (3) | 0.3860 (3) | 0.1996 (2) | 0.0254 (7) | |
O6' | 0.9424 (2) | 0.3556 (2) | 0.28353 (17) | 0.0334 (5) | |
C7' | 0.6545 (3) | 0.4724 (3) | 0.3310 (2) | 0.0278 (7) | |
H7D | 0.5573 | 0.5200 | 0.3200 | 0.033* | |
C8' | 0.6063 (4) | 0.3530 (3) | 0.4364 (3) | 0.0389 (8) | |
H8D | 0.5269 | 0.3039 | 0.4221 | 0.058* | |
H8E | 0.5634 | 0.3770 | 0.5058 | 0.058* | |
H8F | 0.6978 | 0.3016 | 0.4489 | 0.058* | |
C9' | 0.7644 (4) | 0.5585 (3) | 0.3554 (3) | 0.0373 (8) | |
H9D | 0.7088 | 0.5896 | 0.4177 | 0.056* | |
H9E | 0.8010 | 0.6303 | 0.2846 | 0.056* | |
H9F | 0.8541 | 0.5108 | 0.3795 | 0.056* | |
C10' | 1.1033 (3) | 0.3099 (3) | 0.2692 (3) | 0.0308 (7) | |
H10D | 1.1592 | 0.3456 | 0.1859 | 0.037* | |
C11' | 1.0971 (4) | 0.1684 (3) | 0.3060 (3) | 0.0442 (9) | |
H11D | 1.0420 | 0.1408 | 0.2568 | 0.066* | |
H11E | 1.0418 | 0.1339 | 0.3875 | 0.066* | |
H11F | 1.2037 | 0.1377 | 0.2976 | 0.066* | |
C12' | 1.1786 (4) | 0.3621 (3) | 0.3443 (3) | 0.0422 (9) | |
H12D | 1.1760 | 0.4547 | 0.3171 | 0.063* | |
H12E | 1.2873 | 0.3365 | 0.3390 | 0.063* | |
H12F | 1.1213 | 0.3289 | 0.4255 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0242 (13) | 0.0291 (13) | 0.0214 (13) | −0.0025 (11) | 0.0009 (11) | −0.0074 (10) |
C2 | 0.0255 (16) | 0.0267 (15) | 0.0205 (16) | 0.0046 (13) | −0.0038 (13) | −0.0014 (12) |
O2 | 0.0294 (12) | 0.0380 (12) | 0.0280 (12) | 0.0011 (10) | 0.0006 (10) | −0.0130 (10) |
N3 | 0.0222 (13) | 0.0292 (13) | 0.0236 (14) | −0.0030 (11) | 0.0036 (11) | −0.0069 (10) |
C4 | 0.0304 (17) | 0.0245 (15) | 0.0192 (15) | 0.0013 (13) | −0.0054 (13) | −0.0014 (12) |
O4 | 0.0301 (12) | 0.0352 (12) | 0.0293 (12) | −0.0080 (10) | 0.0030 (10) | −0.0097 (9) |
C5 | 0.0278 (16) | 0.0237 (14) | 0.0173 (15) | −0.0028 (12) | 0.0007 (13) | −0.0034 (11) |
C6 | 0.0259 (16) | 0.0266 (15) | 0.0145 (15) | 0.0014 (13) | 0.0004 (13) | −0.0012 (11) |
O6 | 0.0241 (11) | 0.0385 (12) | 0.0185 (11) | −0.0047 (9) | 0.0005 (9) | −0.0066 (9) |
C7 | 0.0301 (18) | 0.0425 (19) | 0.0362 (19) | −0.0095 (15) | 0.0075 (15) | −0.0224 (15) |
C8 | 0.052 (2) | 0.041 (2) | 0.071 (3) | −0.0031 (18) | 0.014 (2) | −0.0274 (19) |
C9 | 0.046 (2) | 0.094 (3) | 0.035 (2) | −0.016 (2) | 0.0049 (19) | −0.032 (2) |
C10 | 0.0232 (16) | 0.0363 (17) | 0.0251 (16) | −0.0027 (13) | −0.0044 (13) | −0.0080 (13) |
C11 | 0.0329 (19) | 0.053 (2) | 0.0327 (19) | 0.0027 (16) | −0.0044 (16) | −0.0025 (16) |
C12 | 0.0269 (18) | 0.060 (2) | 0.037 (2) | −0.0088 (16) | 0.0018 (16) | −0.0112 (17) |
N1' | 0.0241 (13) | 0.0333 (13) | 0.0209 (13) | 0.0051 (11) | −0.0034 (11) | −0.0079 (10) |
C2' | 0.0288 (17) | 0.0279 (16) | 0.0210 (16) | −0.0010 (13) | −0.0033 (14) | −0.0053 (12) |
O2' | 0.0351 (13) | 0.0496 (14) | 0.0224 (12) | 0.0056 (10) | −0.0035 (10) | −0.0145 (10) |
N3' | 0.0267 (14) | 0.0312 (13) | 0.0211 (13) | 0.0041 (11) | −0.0075 (11) | −0.0084 (10) |
C4' | 0.0310 (17) | 0.0222 (14) | 0.0184 (15) | −0.0017 (13) | −0.0014 (13) | −0.0038 (11) |
O4' | 0.0250 (12) | 0.0326 (11) | 0.0240 (11) | 0.0056 (9) | −0.0055 (9) | −0.0067 (9) |
C5' | 0.0271 (16) | 0.0247 (15) | 0.0182 (15) | 0.0012 (12) | −0.0038 (13) | −0.0056 (11) |
C6' | 0.0271 (17) | 0.0299 (15) | 0.0161 (15) | −0.0002 (13) | −0.0029 (13) | −0.0041 (12) |
O6' | 0.0262 (12) | 0.0510 (13) | 0.0215 (11) | 0.0112 (10) | −0.0059 (9) | −0.0102 (9) |
C7' | 0.0249 (16) | 0.0367 (17) | 0.0193 (16) | 0.0042 (13) | −0.0006 (13) | −0.0086 (13) |
C8' | 0.0340 (19) | 0.056 (2) | 0.0191 (17) | 0.0015 (16) | −0.0013 (14) | −0.0047 (14) |
C9' | 0.039 (2) | 0.0462 (19) | 0.0300 (18) | 0.0056 (16) | −0.0091 (16) | −0.0157 (15) |
C10' | 0.0232 (17) | 0.0409 (18) | 0.0258 (17) | 0.0070 (14) | −0.0024 (14) | −0.0099 (14) |
C11' | 0.045 (2) | 0.0414 (19) | 0.042 (2) | 0.0084 (16) | −0.0062 (18) | −0.0099 (16) |
C12' | 0.0320 (19) | 0.061 (2) | 0.035 (2) | 0.0024 (17) | −0.0080 (16) | −0.0167 (17) |
Geometric parameters (Å, º) top
N1—C6 | 1.375 (4) | N1'—C6' | 1.377 (4) |
N1—C2 | 1.380 (4) | N1'—C2' | 1.387 (4) |
N1—H1A | 0.8800 | N1'—H1D | 0.8800 |
C2—O2 | 1.237 (3) | C2'—O2' | 1.226 (3) |
C2—N3 | 1.354 (4) | C2'—N3' | 1.378 (4) |
N3—C4 | 1.398 (4) | N3'—C4' | 1.388 (4) |
N3—H3A | 0.8800 | N3'—H3D | 0.8800 |
C4—O4 | 1.235 (3) | C4'—O4' | 1.273 (3) |
C4—C5 | 1.446 (4) | C4'—C5' | 1.426 (4) |
C5—C6 | 1.355 (4) | C5'—C6' | 1.385 (4) |
C5—C7 | 1.524 (4) | C5'—C7' | 1.525 (4) |
C6—O6 | 1.355 (3) | C6'—O6' | 1.339 (3) |
O6—C10 | 1.478 (3) | O6'—C10' | 1.478 (4) |
C7—C9 | 1.528 (5) | C7'—C9' | 1.523 (4) |
C7—C8 | 1.535 (5) | C7'—C8' | 1.531 (4) |
C7—H7A | 1.0000 | C7'—H7D | 1.0000 |
C8—H8A | 0.9800 | C8'—H8D | 0.9800 |
C8—H8B | 0.9800 | C8'—H8E | 0.9800 |
C8—H8C | 0.9800 | C8'—H8F | 0.9800 |
C9—H9A | 0.9800 | C9'—H9D | 0.9800 |
C9—H9B | 0.9800 | C9'—H9E | 0.9800 |
C9—H9C | 0.9800 | C9'—H9F | 0.9800 |
C10—C12 | 1.508 (4) | C10'—C11' | 1.497 (4) |
C10—C11 | 1.515 (4) | C10'—C12' | 1.513 (4) |
C10—H10A | 1.0000 | C10'—H10D | 1.0000 |
C11—H11A | 0.9800 | C11'—H11D | 0.9800 |
C11—H11B | 0.9800 | C11'—H11E | 0.9800 |
C11—H11C | 0.9800 | C11'—H11F | 0.9800 |
C12—H12A | 0.9800 | C12'—H12D | 0.9800 |
C12—H12B | 0.9800 | C12'—H12E | 0.9800 |
C12—H12C | 0.9800 | C12'—H12F | 0.9800 |
| | | |
C6—N1—C2 | 123.0 (2) | C6'—N1'—C2' | 122.7 (2) |
C6—N1—H1A | 118.5 | C6'—N1'—H1D | 118.6 |
C2—N1—H1A | 118.5 | C2'—N1'—H1D | 118.6 |
O2—C2—N3 | 123.5 (3) | O2'—C2'—N3' | 123.6 (3) |
O2—C2—N1 | 121.6 (3) | O2'—C2'—N1' | 122.1 (3) |
N3—C2—N1 | 114.9 (3) | N3'—C2'—N1' | 114.3 (3) |
C2—N3—C4 | 125.7 (3) | C2'—N3'—C4' | 125.9 (2) |
C2—N3—H3A | 117.2 | C2'—N3'—H3D | 117.0 |
C4—N3—H3A | 117.2 | C4'—N3'—H3D | 117.0 |
O4—C4—N3 | 118.0 (3) | O4'—C4'—N3' | 117.8 (2) |
O4—C4—C5 | 124.9 (3) | O4'—C4'—C5' | 124.5 (3) |
N3—C4—C5 | 117.0 (3) | N3'—C4'—C5' | 117.8 (3) |
C6—C5—C4 | 117.1 (3) | C6'—C5'—C4' | 117.0 (3) |
C6—C5—C7 | 121.4 (3) | C6'—C5'—C7' | 122.3 (3) |
C4—C5—C7 | 121.5 (2) | C4'—C5'—C7' | 120.7 (3) |
O6—C6—C5 | 120.6 (3) | O6'—C6'—N1' | 119.4 (3) |
O6—C6—N1 | 117.0 (2) | O6'—C6'—C5' | 118.4 (3) |
C5—C6—N1 | 122.4 (3) | N1'—C6'—C5' | 122.2 (3) |
C6—O6—C10 | 118.4 (2) | C6'—O6'—C10' | 124.0 (2) |
C5—C7—C9 | 112.0 (3) | C9'—C7'—C5' | 113.2 (2) |
C5—C7—C8 | 110.7 (3) | C9'—C7'—C8' | 111.0 (2) |
C9—C7—C8 | 112.5 (3) | C5'—C7'—C8' | 112.4 (2) |
C5—C7—H7A | 107.1 | C9'—C7'—H7D | 106.6 |
C9—C7—H7A | 107.1 | C5'—C7'—H7D | 106.6 |
C8—C7—H7A | 107.1 | C8'—C7'—H7D | 106.6 |
C7—C8—H8A | 109.5 | C7'—C8'—H8D | 109.5 |
C7—C8—H8B | 109.5 | C7'—C8'—H8E | 109.5 |
H8A—C8—H8B | 109.5 | H8D—C8'—H8E | 109.5 |
C7—C8—H8C | 109.5 | C7'—C8'—H8F | 109.5 |
H8A—C8—H8C | 109.5 | H8D—C8'—H8F | 109.5 |
H8B—C8—H8C | 109.5 | H8E—C8'—H8F | 109.5 |
C7—C9—H9A | 109.5 | C7'—C9'—H9D | 109.5 |
C7—C9—H9B | 109.5 | C7'—C9'—H9E | 109.5 |
H9A—C9—H9B | 109.5 | H9D—C9'—H9E | 109.5 |
C7—C9—H9C | 109.5 | C7'—C9'—H9F | 109.5 |
H9A—C9—H9C | 109.5 | H9D—C9'—H9F | 109.5 |
H9B—C9—H9C | 109.5 | H9E—C9'—H9F | 109.5 |
O6—C10—C12 | 105.0 (2) | O6'—C10'—C11' | 109.2 (3) |
O6—C10—C11 | 110.5 (2) | O6'—C10'—C12' | 104.3 (2) |
C12—C10—C11 | 112.5 (3) | C11'—C10'—C12' | 113.7 (3) |
O6—C10—H10A | 109.6 | O6'—C10'—H10D | 109.8 |
C12—C10—H10A | 109.6 | C11'—C10'—H10D | 109.8 |
C11—C10—H10A | 109.6 | C12'—C10'—H10D | 109.8 |
C10—C11—H11A | 109.5 | C10'—C11'—H11D | 109.5 |
C10—C11—H11B | 109.5 | C10'—C11'—H11E | 109.5 |
H11A—C11—H11B | 109.5 | H11D—C11'—H11E | 109.5 |
C10—C11—H11C | 109.5 | C10'—C11'—H11F | 109.5 |
H11A—C11—H11C | 109.5 | H11D—C11'—H11F | 109.5 |
H11B—C11—H11C | 109.5 | H11E—C11'—H11F | 109.5 |
C10—C12—H12A | 109.5 | C10'—C12'—H12D | 109.5 |
C10—C12—H12B | 109.5 | C10'—C12'—H12E | 109.5 |
H12A—C12—H12B | 109.5 | H12D—C12'—H12E | 109.5 |
C10—C12—H12C | 109.5 | C10'—C12'—H12F | 109.5 |
H12A—C12—H12C | 109.5 | H12D—C12'—H12F | 109.5 |
H12B—C12—H12C | 109.5 | H12E—C12'—H12F | 109.5 |
| | | |
C6—N1—C2—O2 | −178.4 (3) | O4'—C4'—C5'—C6' | −178.8 (3) |
C6—N1—C2—N3 | 0.9 (4) | N3'—C4'—C5'—C6' | 0.5 (4) |
O2—C2—N3—C4 | 177.5 (3) | O4'—C4'—C5'—C7' | 2.3 (4) |
N1—C2—N3—C4 | −1.7 (4) | N3'—C4'—C5'—C7' | −178.5 (2) |
C2—N3—C4—O4 | −176.4 (2) | C2'—N1'—C6'—O6' | 178.0 (2) |
C2—N3—C4—C5 | 1.5 (4) | C2'—N1'—C6'—C5' | −1.3 (4) |
O4—C4—C5—C6 | 177.4 (3) | C4'—C5'—C6'—O6' | −178.0 (2) |
N3—C4—C5—C6 | −0.4 (4) | C7'—C5'—C6'—O6' | 0.9 (4) |
O4—C4—C5—C7 | −1.2 (4) | C4'—C5'—C6'—N1' | 1.3 (4) |
N3—C4—C5—C7 | −179.0 (3) | C7'—C5'—C6'—N1' | −179.8 (2) |
C4—C5—C6—O6 | 178.2 (2) | N1'—C6'—O6'—C10' | 8.6 (4) |
C7—C5—C6—O6 | −3.2 (4) | C6'—C5'—C7'—C9' | 57.6 (4) |
C4—C5—C6—N1 | −0.3 (4) | C6'—C5'—C7'—C8' | −69.1 (4) |
C7—C5—C6—N1 | 178.3 (3) | C6—C5—C7—C8 | −114.9 (3) |
C2—N1—C6—O6 | −178.4 (2) | C4—C5—C7—C8 | 63.6 (4) |
C2—N1—C6—C5 | 0.1 (4) | C4—C5—C7—C9 | −62.8 (4) |
N1—C6—O6—C10 | −42.8 (3) | C5—C6—O6—C10 | 138.6 (3) |
C6—C5—C7—C9 | 118.6 (3) | C6—O6—C10—C11 | −56.1 (3) |
C6'—N1'—C2'—O2' | 178.4 (3) | C6—O6—C10—C12 | −177.6 (2) |
C6'—N1'—C2'—N3' | −0.5 (4) | C4'—C5'—C7'—C8' | 109.8 (3) |
O2'—C2'—N3'—C4' | −176.5 (3) | C4'—C5'—C7'—C9' | −123.5 (3) |
N1'—C2'—N3'—C4' | 2.4 (4) | C5'—C6'—O6'—C10' | −172.1 (3) |
C2'—N3'—C4'—O4' | 176.8 (2) | C6'—O6'—C10'—C11' | −91.4 (3) |
C2'—N3'—C4'—C5' | −2.4 (4) | C6'—O6'—C10'—C12' | 146.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4′ | 0.88 | 2.01 | 2.814 (3) | 150 |
N3—H3A···O4i | 0.88 | 2.01 | 2.863 (3) | 163 |
N1′—H1D···O2ii | 0.88 | 1.96 | 2.814 (3) | 165 |
N3′—H3D···O4′iii | 0.88 | 1.97 | 2.853 (3) | 176 |
Symmetry codes: (i) −x+2, −y+2, −z; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z. |