In the solid state, the title compound, C
14H
13NO
2, crystallizes as a zwitterion. Two molecules comprise the asymmetric unit. The molecules exhibit two types of hydrogen bonds: N—H
O hydrogen bonds involving hydroxy and imine groups generate an
S(6) ring motif, and O—H
O hydrogen bonds linking two symmetry-related molecules form a centrosymmetric dimer.
Supporting information
CCDC reference: 655596
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.127
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O11
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O21
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 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
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2006); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2007) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
2-Hydroxy-6-[(
m-tolyliminio)methyl]phenolate
top
Crystal data top
C14H13NO2 | Z = 4 |
Mr = 227.25 | F(000) = 480 |
Triclinic, P1 | The final unit cell was obtained from the xyz centroids of
2168 reflections after integration using the SAINT-Plus
software package (Bruker, 2000). Reduced cell calculations did not indicate any higher metric lattice symmetry
and examination of the final atomic coordinates of the structure did not
yield extra symmetry elements (Spek, 1988; Le Page 1987, 1988) |
Hall symbol: -P 1 | Dx = 1.360 Mg m−3 |
a = 7.7094 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5939 (9) Å | Cell parameters from 2168 reflections |
c = 14.8307 (13) Å | θ = 2.8–27.3° |
α = 72.2740 (15)° | µ = 0.09 mm−1 |
β = 83.0670 (16)° | T = 100 K |
γ = 74.2580 (15)° | Block, red |
V = 1109.52 (17) Å3 | 0.39 × 0.17 × 0.12 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4253 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 2951 reflections with I > 2σ(I) |
Parallel mounted graphite monochromator | Rint = 0.027 |
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1 | θmax = 26.0°, θmin = 2.8° |
φ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2006) | k = −12→13 |
Tmin = 0.955, Tmax = 0.989 | l = −18→18 |
7014 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0682P)2] where P = (Fo2 + 2Fc2)/3 |
4253 reflections | (Δ/σ)max < 0.001 |
315 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su'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 | |
O11 | −0.30956 (17) | 0.46121 (13) | 0.44824 (10) | 0.0294 (4) | |
O12 | −0.61344 (18) | 0.62343 (14) | 0.35839 (11) | 0.0319 (5) | |
N1 | 0.0301 (2) | 0.37546 (15) | 0.44598 (11) | 0.0229 (5) | |
C11 | −0.2912 (3) | 0.54424 (18) | 0.36417 (13) | 0.0233 (6) | |
C12 | −0.4475 (3) | 0.63121 (19) | 0.31473 (14) | 0.0249 (6) | |
C13 | −0.4334 (3) | 0.71750 (19) | 0.22577 (14) | 0.0262 (6) | |
C14 | −0.2624 (3) | 0.72581 (19) | 0.18151 (14) | 0.0286 (6) | |
C15 | −0.1079 (3) | 0.64563 (19) | 0.22702 (13) | 0.0269 (6) | |
C16 | −0.1193 (3) | 0.55269 (18) | 0.31780 (13) | 0.0234 (6) | |
C17 | 0.0402 (3) | 0.46546 (19) | 0.36446 (13) | 0.0233 (6) | |
C18 | 0.1736 (3) | 0.27812 (18) | 0.49996 (13) | 0.0220 (6) | |
C19 | 0.3529 (3) | 0.25659 (19) | 0.46668 (13) | 0.0236 (6) | |
C110 | 0.4880 (3) | 0.16019 (19) | 0.52310 (13) | 0.0233 (6) | |
C111 | 0.4389 (3) | 0.08514 (19) | 0.61330 (14) | 0.0250 (6) | |
C112 | 0.2597 (3) | 0.10638 (19) | 0.64576 (14) | 0.0255 (6) | |
C113 | 0.1267 (3) | 0.20312 (19) | 0.58927 (13) | 0.0244 (6) | |
C114 | 0.6833 (3) | 0.1366 (2) | 0.48869 (14) | 0.0276 (6) | |
H11 | −0.100 (3) | 0.388 (2) | 0.4670 (14) | 0.0331* | |
H12 | −0.605 (3) | 0.573 (2) | 0.4203 (16) | 0.0414* | |
H13 | −0.53950 | 0.77225 | 0.19351 | 0.0315* | |
H14 | −0.25413 | 0.78699 | 0.12011 | 0.0343* | |
H15 | 0.00682 | 0.65269 | 0.19740 | 0.0323* | |
H17 | 0.15512 | 0.47332 | 0.33554 | 0.0279* | |
H19 | 0.38328 | 0.30804 | 0.40501 | 0.0283* | |
H111 | 0.52913 | 0.01890 | 0.65276 | 0.0301* | |
H112 | 0.22822 | 0.05432 | 0.70700 | 0.0305* | |
H113 | 0.00417 | 0.21789 | 0.61164 | 0.0292* | |
H114 | 0.69231 | 0.19175 | 0.42273 | 0.0414* | |
H114' | 0.73242 | 0.03956 | 0.49277 | 0.0414* | |
H114'' | 0.75207 | 0.16320 | 0.52821 | 0.0414* | |
O21 | 0.96821 (18) | 0.15125 (13) | 0.01479 (9) | 0.0283 (4) | |
O22 | 1.14752 (19) | −0.09574 (13) | 0.13003 (9) | 0.0307 (4) | |
N2 | 0.8077 (2) | 0.40206 (15) | −0.00512 (11) | 0.0233 (5) | |
C21 | 1.0044 (2) | 0.14475 (19) | 0.10049 (13) | 0.0223 (6) | |
C22 | 1.0979 (3) | 0.01771 (19) | 0.16170 (13) | 0.0239 (6) | |
C23 | 1.1390 (3) | 0.0095 (2) | 0.25099 (13) | 0.0264 (6) | |
C24 | 1.0891 (3) | 0.1252 (2) | 0.28508 (14) | 0.0299 (7) | |
C25 | 0.9982 (3) | 0.2484 (2) | 0.22875 (14) | 0.0300 (7) | |
C26 | 0.9559 (3) | 0.26065 (19) | 0.13608 (13) | 0.0241 (6) | |
C27 | 0.8554 (2) | 0.38820 (19) | 0.07914 (13) | 0.0237 (6) | |
C28 | 0.6973 (3) | 0.51979 (18) | −0.06579 (13) | 0.0228 (6) | |
C29 | 0.6510 (3) | 0.64800 (19) | −0.04945 (13) | 0.0242 (6) | |
C210 | 0.5397 (3) | 0.75956 (19) | −0.11050 (14) | 0.0266 (6) | |
C211 | 0.4770 (3) | 0.7407 (2) | −0.18876 (14) | 0.0279 (6) | |
C212 | 0.5210 (3) | 0.6128 (2) | −0.20462 (14) | 0.0277 (6) | |
C213 | 0.6311 (3) | 0.5021 (2) | −0.14345 (13) | 0.0253 (6) | |
C214 | 0.4838 (3) | 0.89667 (19) | −0.09069 (15) | 0.0339 (7) | |
H21 | 0.84194 | 0.32882 | −0.02454 | 0.0406* | |
H22 | 1.10678 | −0.07693 | 0.07670 | 0.0507* | |
H23 | 1.20220 | −0.07562 | 0.29049 | 0.0317* | |
H24 | 1.11841 | 0.11778 | 0.34719 | 0.0359* | |
H25 | 0.96347 | 0.32610 | 0.25221 | 0.0360* | |
H27 | 0.82237 | 0.46507 | 0.10348 | 0.0284* | |
H29 | 0.69588 | 0.65928 | 0.00377 | 0.0291* | |
H211 | 0.40315 | 0.81636 | −0.23179 | 0.0335* | |
H212 | 0.47534 | 0.60130 | −0.25754 | 0.0332* | |
H213 | 0.66145 | 0.41471 | −0.15429 | 0.0303* | |
H214 | 0.36087 | 0.91025 | −0.06248 | 0.0507* | |
H214' | 0.48750 | 0.96918 | −0.15007 | 0.0507* | |
H214'' | 0.56659 | 0.89974 | −0.04665 | 0.0507* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O11 | 0.0243 (7) | 0.0238 (7) | 0.0328 (8) | −0.0047 (6) | −0.0006 (6) | 0.0013 (6) |
O12 | 0.0235 (8) | 0.0288 (8) | 0.0377 (9) | −0.0037 (6) | −0.0048 (6) | −0.0024 (7) |
N1 | 0.0209 (9) | 0.0205 (9) | 0.0246 (9) | −0.0020 (7) | −0.0017 (7) | −0.0050 (7) |
C11 | 0.0259 (11) | 0.0175 (10) | 0.0269 (11) | −0.0037 (8) | −0.0030 (8) | −0.0077 (8) |
C12 | 0.0228 (10) | 0.0201 (10) | 0.0335 (12) | −0.0048 (8) | −0.0040 (8) | −0.0094 (9) |
C13 | 0.0282 (11) | 0.0197 (10) | 0.0308 (12) | 0.0002 (8) | −0.0100 (9) | −0.0094 (9) |
C14 | 0.0358 (12) | 0.0230 (10) | 0.0243 (11) | −0.0020 (9) | −0.0022 (9) | −0.0071 (9) |
C15 | 0.0277 (11) | 0.0255 (11) | 0.0246 (11) | −0.0026 (9) | 0.0016 (8) | −0.0074 (9) |
C16 | 0.0253 (10) | 0.0194 (10) | 0.0258 (11) | −0.0029 (8) | −0.0030 (8) | −0.0086 (8) |
C17 | 0.0217 (10) | 0.0233 (10) | 0.0256 (11) | −0.0037 (8) | 0.0002 (8) | −0.0103 (9) |
C18 | 0.0242 (10) | 0.0180 (10) | 0.0231 (10) | −0.0007 (8) | −0.0056 (8) | −0.0072 (8) |
C19 | 0.0282 (11) | 0.0211 (10) | 0.0213 (10) | −0.0067 (8) | 0.0003 (8) | −0.0058 (8) |
C110 | 0.0228 (10) | 0.0213 (10) | 0.0287 (11) | −0.0058 (8) | −0.0031 (8) | −0.0102 (8) |
C111 | 0.0262 (11) | 0.0211 (10) | 0.0277 (11) | −0.0039 (8) | −0.0093 (8) | −0.0054 (8) |
C112 | 0.0298 (11) | 0.0239 (10) | 0.0229 (10) | −0.0093 (9) | −0.0029 (8) | −0.0040 (8) |
C113 | 0.0236 (10) | 0.0246 (10) | 0.0267 (11) | −0.0064 (8) | −0.0009 (8) | −0.0095 (9) |
C114 | 0.0245 (11) | 0.0263 (11) | 0.0304 (11) | −0.0042 (9) | −0.0033 (8) | −0.0069 (9) |
O21 | 0.0370 (8) | 0.0228 (7) | 0.0231 (8) | −0.0030 (6) | −0.0063 (6) | −0.0057 (6) |
O22 | 0.0381 (8) | 0.0217 (7) | 0.0294 (8) | −0.0007 (6) | −0.0118 (6) | −0.0052 (6) |
N2 | 0.0252 (9) | 0.0181 (8) | 0.0254 (9) | −0.0032 (7) | −0.0015 (7) | −0.0063 (7) |
C21 | 0.0197 (10) | 0.0252 (10) | 0.0211 (10) | −0.0067 (8) | 0.0012 (8) | −0.0050 (8) |
C22 | 0.0211 (10) | 0.0241 (10) | 0.0254 (11) | −0.0061 (8) | −0.0025 (8) | −0.0046 (8) |
C23 | 0.0222 (10) | 0.0267 (11) | 0.0260 (11) | −0.0062 (9) | −0.0046 (8) | 0.0000 (9) |
C24 | 0.0293 (11) | 0.0378 (12) | 0.0223 (11) | −0.0051 (10) | −0.0042 (9) | −0.0096 (9) |
C25 | 0.0297 (11) | 0.0310 (11) | 0.0302 (12) | −0.0034 (9) | −0.0036 (9) | −0.0128 (9) |
C26 | 0.0204 (10) | 0.0245 (10) | 0.0271 (11) | −0.0054 (8) | −0.0014 (8) | −0.0070 (9) |
C27 | 0.0211 (10) | 0.0228 (10) | 0.0276 (11) | −0.0055 (8) | 0.0008 (8) | −0.0085 (8) |
C28 | 0.0218 (10) | 0.0210 (10) | 0.0218 (10) | −0.0060 (8) | 0.0040 (8) | −0.0018 (8) |
C29 | 0.0250 (10) | 0.0240 (10) | 0.0230 (10) | −0.0087 (8) | 0.0035 (8) | −0.0051 (8) |
C210 | 0.0226 (10) | 0.0220 (10) | 0.0304 (12) | −0.0061 (8) | 0.0054 (8) | −0.0026 (9) |
C211 | 0.0241 (10) | 0.0236 (11) | 0.0273 (11) | −0.0043 (8) | 0.0012 (8) | 0.0030 (9) |
C212 | 0.0278 (11) | 0.0301 (11) | 0.0238 (11) | −0.0086 (9) | 0.0007 (8) | −0.0049 (9) |
C213 | 0.0249 (10) | 0.0240 (10) | 0.0259 (11) | −0.0065 (8) | 0.0036 (8) | −0.0069 (9) |
C214 | 0.0329 (12) | 0.0218 (11) | 0.0421 (13) | −0.0032 (9) | 0.0011 (10) | −0.0063 (9) |
Geometric parameters (Å, º) top
O11—C11 | 1.306 (2) | C111—H111 | 0.9500 |
O12—C12 | 1.374 (3) | C112—H112 | 0.9500 |
O12—H12 | 0.91 (2) | C113—H113 | 0.9500 |
O21—C21 | 1.311 (2) | C114—H114 | 0.9800 |
O22—C22 | 1.365 (2) | C114—H114'' | 0.9800 |
O22—H22 | 0.8300 | C114—H114' | 0.9800 |
N1—C18 | 1.421 (3) | C21—C22 | 1.429 (3) |
N1—C17 | 1.301 (2) | C21—C26 | 1.423 (3) |
N1—H11 | 1.00 (2) | C22—C23 | 1.370 (3) |
N2—C28 | 1.420 (3) | C23—C24 | 1.407 (3) |
N2—C27 | 1.299 (2) | C24—C25 | 1.369 (3) |
N2—H21 | 0.8700 | C25—C26 | 1.410 (3) |
C11—C12 | 1.428 (3) | C26—C27 | 1.426 (3) |
C11—C16 | 1.430 (3) | C28—C213 | 1.396 (3) |
C12—C13 | 1.369 (3) | C28—C29 | 1.396 (3) |
C13—C14 | 1.413 (3) | C29—C210 | 1.392 (3) |
C14—C15 | 1.375 (3) | C23—H23 | 0.9500 |
C15—C16 | 1.415 (3) | C24—H24 | 0.9500 |
C16—C17 | 1.430 (3) | C25—H25 | 0.9500 |
C18—C19 | 1.393 (3) | C27—H27 | 0.9500 |
C18—C113 | 1.384 (3) | C29—H29 | 0.9500 |
C19—C110 | 1.393 (3) | C210—C211 | 1.396 (3) |
C110—C114 | 1.509 (3) | C210—C214 | 1.507 (3) |
C110—C111 | 1.399 (3) | C211—C212 | 1.390 (3) |
C111—C112 | 1.388 (3) | C212—C213 | 1.385 (3) |
C112—C113 | 1.385 (3) | C211—H211 | 0.9500 |
C13—H13 | 0.9500 | C212—H212 | 0.9500 |
C14—H14 | 0.9500 | C213—H213 | 0.9500 |
C15—H15 | 0.9500 | C214—H214' | 0.9800 |
C17—H17 | 0.9500 | C214—H214'' | 0.9800 |
C19—H19 | 0.9500 | C214—H214 | 0.9800 |
| | | |
O11···O12 | 2.719 (2) | C112···H114'ix | 2.9100 |
O11···N1 | 2.528 (2) | C212···C27iv | 3.253 (3) |
O11···C114i | 3.321 (3) | C113···H114'ix | 3.0600 |
O11···O12ii | 2.774 (2) | C214···C22vii | 3.538 (3) |
O11···O11ii | 3.166 (2) | C212···H17iv | 3.0800 |
O12···O11ii | 2.774 (2) | C212···H19iv | 2.8900 |
O12···O11 | 2.719 (2) | C212···H27iv | 3.0700 |
O21···N2 | 2.550 (2) | C213···H15iv | 2.9800 |
O21···O22iii | 2.6965 (19) | C213···H17iv | 3.0900 |
O21···O22 | 2.7501 (19) | H114'···C111ix | 2.9500 |
O22···O21iii | 2.6965 (19) | H114'···C112ix | 2.9100 |
O22···O21 | 2.7501 (19) | H114'···C113ix | 3.0600 |
O11···H12ii | 1.94 (2) | H114''···H23xii | 2.6000 |
O11···H12 | 2.29 (2) | H214'···H211 | 2.5400 |
O11···H11 | 1.61 (2) | H214'···C13xi | 3.0900 |
O12···H17i | 2.8000 | H214''···H29 | 2.3800 |
O21···H22iii | 1.9700 | H11···O11 | 1.61 (2) |
O21···H14iv | 2.8700 | H11···C11 | 2.22 (2) |
O21···H21 | 1.8200 | H11···H113 | 2.4000 |
O21···H214iv | 2.7500 | H12···O11 | 2.29 (2) |
O21···H22 | 2.3000 | H12···O11ii | 1.94 (2) |
O22···H13v | 2.5700 | H13···O22xiv | 2.5700 |
N1···O11 | 2.528 (2) | H14···O21iv | 2.8700 |
N2···O21 | 2.550 (2) | H15···H213iv | 2.5200 |
C11···C113vi | 3.525 (3) | H15···H17 | 2.4800 |
C11···C18vi | 3.479 (3) | H15···C213iv | 2.9800 |
C12···C111vi | 3.500 (3) | H17···O12viii | 2.8000 |
C14···C112vi | 3.540 (3) | H17···C19 | 2.7300 |
C15···C113vi | 3.528 (3) | H17···H15 | 2.4800 |
C15···C112vi | 3.557 (3) | H17···H19 | 2.2100 |
C16···C113vi | 3.266 (3) | H17···C213iv | 3.0900 |
C17···C25i | 3.581 (3) | H17···C212iv | 3.0800 |
C18···C11vi | 3.479 (3) | H19···H17 | 2.2100 |
C22···C214vii | 3.538 (3) | H19···C17 | 2.7400 |
C25···C17viii | 3.581 (3) | H19···H212iv | 2.3700 |
C26···C211iv | 3.337 (3) | H19···H114 | 2.3700 |
C26···C29vii | 3.416 (3) | H19···C212iv | 2.8900 |
C27···C212iv | 3.253 (3) | H21···O21 | 1.8200 |
C27···C211iv | 3.258 (3) | H21···C21 | 2.4200 |
C28···C28iv | 3.464 (3) | H21···H213 | 2.3200 |
C28···C29iv | 3.595 (3) | H22···O21 | 2.3000 |
C29···C26vii | 3.416 (3) | H22···O21iii | 1.9700 |
C29···C28iv | 3.595 (3) | H23···H114''xii | 2.6000 |
C111···C114ix | 3.522 (3) | H23···H113ix | 2.5100 |
C11···H11 | 2.22 (2) | H25···C16viii | 2.7500 |
C111···C12vi | 3.500 (3) | H25···C17viii | 2.7400 |
C112···C15vi | 3.557 (3) | H25···H27 | 2.4400 |
C112···C14vi | 3.540 (3) | H27···C212iv | 3.0700 |
C12···H212x | 2.9000 | H27···C29 | 2.7000 |
C13···H213x | 2.9800 | H27···H25 | 2.4400 |
C13···H214'xi | 3.0900 | H27···H29 | 2.1900 |
C113···C15vi | 3.528 (3) | H29···H214'' | 2.3800 |
C113···C11vi | 3.525 (3) | H29···H27 | 2.1900 |
C113···C16vi | 3.266 (3) | H29···C27 | 2.7300 |
C14···H29i | 3.0000 | H29···C14viii | 3.0000 |
C114···O11viii | 3.321 (3) | H111···C24xii | 3.0300 |
C114···C111ix | 3.522 (3) | H111···C23xii | 2.9800 |
C16···H25i | 2.7500 | H112···H211xiii | 2.4600 |
C17···H25i | 2.7400 | H112···C23ix | 3.0400 |
C17···H19 | 2.7400 | H113···H23ix | 2.5100 |
C19···H17 | 2.7300 | H113···H11 | 2.4000 |
C21···H21 | 2.4200 | H113···C23ix | 3.0100 |
C23···H111xii | 2.9800 | H114···H19 | 2.3700 |
C23···H113ix | 3.0100 | H211···C112xv | 3.0300 |
C23···H112ix | 3.0400 | H211···H214' | 2.5400 |
C24···H111xii | 3.0300 | H211···H112xv | 2.4600 |
C27···H29 | 2.7300 | H212···C12x | 2.9000 |
C29···H27 | 2.7000 | H212···H19iv | 2.3700 |
C111···H114'ix | 2.9500 | H213···H21 | 2.3200 |
C211···C26iv | 3.337 (3) | H213···C13x | 2.9800 |
C211···C27iv | 3.258 (3) | H213···H15iv | 2.5200 |
C112···H211xiii | 3.0300 | H214···O21iv | 2.7500 |
| | | |
C12—O12—H12 | 112.3 (15) | H114'—C114—H114'' | 109.00 |
C22—O22—H22 | 109.00 | C110—C114—H114'' | 109.00 |
C17—N1—C18 | 128.16 (18) | H114''—C114—H114 | 109.00 |
C18—N1—H11 | 124.2 (12) | C110—C114—H114' | 109.00 |
C17—N1—H11 | 107.7 (12) | O21—C21—C22 | 119.87 (18) |
C27—N2—C28 | 127.22 (17) | O21—C21—C26 | 122.64 (17) |
C27—N2—H21 | 116.00 | C22—C21—C26 | 117.48 (17) |
C28—N2—H21 | 117.00 | O22—C22—C23 | 120.09 (18) |
O11—C11—C12 | 119.7 (2) | O22—C22—C21 | 119.27 (16) |
O11—C11—C16 | 122.90 (19) | C21—C22—C23 | 120.64 (18) |
C12—C11—C16 | 117.37 (17) | C22—C23—C24 | 121.03 (19) |
O12—C12—C13 | 120.8 (2) | C23—C24—C25 | 119.99 (19) |
O12—C12—C11 | 117.88 (17) | C24—C25—C26 | 120.37 (19) |
C11—C12—C13 | 121.3 (2) | C25—C26—C27 | 119.97 (18) |
C12—C13—C14 | 120.6 (2) | C21—C26—C27 | 119.47 (17) |
C13—C14—C15 | 120.22 (19) | C21—C26—C25 | 120.48 (18) |
C14—C15—C16 | 120.2 (2) | N2—C27—C26 | 121.76 (18) |
C11—C16—C17 | 118.95 (17) | N2—C28—C29 | 123.01 (18) |
C15—C16—C17 | 120.7 (2) | N2—C28—C213 | 116.87 (17) |
C11—C16—C15 | 120.3 (2) | C29—C28—C213 | 120.11 (19) |
N1—C17—C16 | 120.9 (2) | C28—C29—C210 | 120.57 (19) |
N1—C18—C113 | 116.4 (2) | C22—C23—H23 | 119.00 |
C19—C18—C113 | 120.49 (19) | C24—C23—H23 | 119.00 |
N1—C18—C19 | 123.11 (17) | C23—C24—H24 | 120.00 |
C18—C19—C110 | 120.52 (18) | C25—C24—H24 | 120.00 |
C19—C110—C114 | 121.28 (18) | C26—C25—H25 | 120.00 |
C111—C110—C114 | 120.28 (19) | C24—C25—H25 | 120.00 |
C19—C110—C111 | 118.5 (2) | C26—C27—H27 | 119.00 |
C110—C111—C112 | 120.7 (2) | N2—C27—H27 | 119.00 |
C111—C112—C113 | 120.30 (19) | C28—C29—H29 | 120.00 |
C18—C113—C112 | 119.5 (2) | C210—C29—H29 | 120.00 |
C14—C13—H13 | 120.00 | C29—C210—C211 | 118.63 (19) |
C12—C13—H13 | 120.00 | C211—C210—C214 | 120.81 (19) |
C15—C14—H14 | 120.00 | C29—C210—C214 | 120.53 (18) |
C13—C14—H14 | 120.00 | C210—C211—C212 | 120.96 (19) |
C16—C15—H15 | 120.00 | C211—C212—C213 | 120.15 (19) |
C14—C15—H15 | 120.00 | C28—C213—C212 | 119.57 (19) |
N1—C17—H17 | 120.00 | C210—C211—H211 | 120.00 |
C16—C17—H17 | 120.00 | C212—C211—H211 | 119.00 |
C110—C19—H19 | 120.00 | C211—C212—H212 | 120.00 |
C18—C19—H19 | 120.00 | C213—C212—H212 | 120.00 |
C112—C111—H111 | 120.00 | C28—C213—H213 | 120.00 |
C110—C111—H111 | 120.00 | C212—C213—H213 | 120.00 |
C111—C112—H112 | 120.00 | C210—C214—H214' | 109.00 |
C113—C112—H112 | 120.00 | C210—C214—H214'' | 109.00 |
C18—C113—H113 | 120.00 | C210—C214—H214 | 109.00 |
C112—C113—H113 | 120.00 | H214'—C214—H214'' | 109.00 |
H114'—C114—H114 | 109.00 | H214'—C214—H214 | 109.00 |
C110—C114—H114 | 109.00 | H214''—C214—H214 | 109.00 |
| | | |
C18—N1—C17—C16 | 177.46 (18) | C18—C19—C110—C114 | −179.28 (19) |
C17—N1—C18—C19 | −6.6 (3) | O21—C21—C22—O22 | −0.4 (3) |
C17—N1—C18—C113 | 173.7 (2) | O21—C21—C22—C23 | 179.10 (19) |
C27—N2—C28—C213 | −166.06 (19) | C26—C21—C22—O22 | −179.70 (19) |
C28—N2—C27—C26 | 175.1 (2) | C26—C21—C22—C23 | −0.3 (3) |
C27—N2—C28—C29 | 12.5 (3) | O21—C21—C26—C25 | −179.88 (19) |
O11—C11—C12—O12 | −0.2 (3) | O21—C21—C26—C27 | 3.5 (3) |
O11—C11—C12—C13 | −178.69 (19) | C22—C21—C26—C25 | −0.6 (3) |
C16—C11—C12—O12 | 179.65 (17) | C22—C21—C26—C27 | −177.22 (19) |
C16—C11—C12—C13 | 1.1 (3) | O22—C22—C23—C24 | −180.0 (2) |
C12—C11—C16—C17 | −178.94 (18) | C21—C22—C23—C24 | 0.6 (3) |
O11—C11—C16—C15 | −179.40 (18) | C22—C23—C24—C25 | −0.1 (4) |
O11—C11—C16—C17 | 0.9 (3) | C23—C24—C25—C26 | −0.8 (4) |
C12—C11—C16—C15 | 0.8 (3) | C24—C25—C26—C21 | 1.1 (3) |
O12—C12—C13—C14 | 179.53 (18) | C24—C25—C26—C27 | 177.7 (2) |
C11—C12—C13—C14 | −2.0 (3) | C21—C26—C27—N2 | −0.6 (3) |
C12—C13—C14—C15 | 0.9 (3) | C25—C26—C27—N2 | −177.2 (2) |
C13—C14—C15—C16 | 1.1 (3) | N2—C28—C29—C210 | −178.9 (2) |
C14—C15—C16—C17 | 177.86 (19) | C213—C28—C29—C210 | −0.4 (3) |
C14—C15—C16—C11 | −1.9 (3) | C29—C28—C213—C212 | 0.7 (3) |
C15—C16—C17—N1 | −176.80 (19) | N2—C28—C213—C212 | 179.3 (2) |
C11—C16—C17—N1 | 2.9 (3) | C28—C29—C210—C214 | 177.6 (2) |
N1—C18—C19—C110 | 179.63 (18) | C28—C29—C210—C211 | −0.6 (3) |
C113—C18—C19—C110 | −0.6 (3) | C29—C210—C211—C212 | 1.4 (3) |
C19—C18—C113—C112 | 0.2 (3) | C214—C210—C211—C212 | −176.8 (2) |
N1—C18—C113—C112 | 179.97 (18) | C210—C211—C212—C213 | −1.2 (3) |
C18—C19—C110—C111 | 0.5 (3) | C211—C212—C213—C28 | 0.1 (3) |
Symmetry codes: (i) x−1, y, z; (ii) −x−1, −y+1, −z+1; (iii) −x+2, −y, −z; (iv) −x+1, −y+1, −z; (v) x+2, y−1, z; (vi) −x, −y+1, −z+1; (vii) −x+2, −y+1, −z; (viii) x+1, y, z; (ix) −x+1, −y, −z+1; (x) −x, −y+1, −z; (xi) −x, −y+2, −z; (xii) −x+2, −y, −z+1; (xiii) x, y−1, z+1; (xiv) x−2, y+1, z; (xv) x, y+1, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O11 | 1.00 (2) | 1.61 (2) | 2.528 (2) | 150.8 (18) |
O12—H12···O11 | 0.91 (2) | 2.29 (2) | 2.719 (2) | 108.7 (18) |
O12—H12···O11ii | 0.91 (2) | 1.94 (2) | 2.774 (2) | 152 (2) |
N2—H21···O21 | 0.8700 | 1.8200 | 2.550 (2) | 140.00 |
O22—H22···O21 | 0.8300 | 2.3000 | 2.7501 (19) | 114.00 |
O22—H22···O21iii | 0.8300 | 1.9700 | 2.6965 (19) | 145.00 |
C13—H13···O22xiv | 0.9500 | 2.5700 | 3.507 (3) | 171.00 |
Symmetry codes: (ii) −x−1, −y+1, −z+1; (iii) −x+2, −y, −z; (xiv) x−2, y+1, z. |