The title compound, C
19H
23N
3O
4, adopts the keto-amine tautomeric form, with the H atom located on N rather than on O. This H atom is involved in a strong intramolecular hydrogen bond. The configuration around the azo N=N double bond is
trans and the dihedral angle between the two aromatic rings is 8.94 (2)°. The molecules, with intramolecular N—H
O hydrogen bonding, are linked by intermolecular O—H
O hydrogen bonds, forming a three-dimensional network.
Supporting information
CCDC reference: 277277
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.010 Å
- Disorder in main residue
- R factor = 0.107
- wR factor = 0.313
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 36 Perc.
Alert level C
RFACG01_ALERT_3_C The value of the R factor is > 0.10
R factor given 0.107
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.313
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.129
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13
PLAT082_ALERT_2_C High R1 Value .................................. 0.11
PLAT084_ALERT_2_C High R2 Value .................................. 0.31
PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
PLAT731_ALERT_1_C Bond Calc 0.83(6), Rep 0.83(2) ...... 3.00 su-Rat
O2 -H2 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.84(5), Rep 0.84(2) ...... 2.50 su-Rat
O3 -H3 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.83(6), Rep 0.83(2) ...... 3.00 su-Rat
O2 -H2 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(5), Rep 0.84(2) ...... 2.50 su-Rat
O3 -H3 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.85(5), Rep 1.85(2) ...... 2.50 su-Rat
H3 -O1 1.555 4.556
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.80 Deg.
C2A -C3 -C2B 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 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
7 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1998).
(
Z)-4-[(
E)-(4-ethylphenyl)diazenyl]-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan- 2-ylamino]methylene}cyclohexa-2,4-dienone
top
Crystal data top
C19H23N3O4 | F(000) = 760 |
Mr = 357.40 | Dx = 1.258 Mg m−3 |
Monoclinic, P21/c | Melting point = 463–465 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.441 (4) Å | Cell parameters from 7373 reflections |
b = 7.8992 (10) Å | θ = 1.6–23.5° |
c = 13.014 (3) Å | µ = 0.09 mm−1 |
β = 95.516 (16)° | T = 296 K |
V = 1887.0 (6) Å3 | Plate, brown |
Z = 4 | 0.50 × 0.40 × 0.12 mm |
Data collection top
Stoe IPDS 2 diffractometer | 1336 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.129 |
Graphite monochromator | θmax = 26.0°, θmin = 2.2° |
Detector resolution: 6.67 pixels mm-1 | h = −22→22 |
w scan rotation | k = −9→9 |
9340 measured reflections | l = −13→16 |
3690 independent reflections | |
Refinement top
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)] = 0.107 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.313 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.157P)2] where P = (Fo2 + 2Fc2)/3 |
3690 reflections | (Δ/σ)max < 0.001 |
238 parameters | Δρmax = 0.47 e Å−3 |
27 restraints | Δρmin = −0.31 e Å−3 |
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 | Occ. (<1) |
C1A | 0.5523 (13) | 1.205 (3) | 0.452 (2) | 0.1031 (4) | 0.396 (14) |
H1A1 | 0.5873 | 1.2835 | 0.4834 | 0.155* | 0.396 (14) |
H1A2 | 0.5616 | 1.0943 | 0.4802 | 0.155* | 0.396 (14) |
H1A3 | 0.5042 | 1.2405 | 0.4640 | 0.155* | 0.396 (14) |
C1B | 0.5824 (8) | 1.295 (2) | 0.4066 (13) | 0.1031 (4) | 0.604 (14) |
H1B1 | 0.6215 | 1.2487 | 0.4519 | 0.155* | 0.604 (14) |
H1B2 | 0.5546 | 1.3722 | 0.4445 | 0.155* | 0.604 (14) |
H1B3 | 0.6021 | 1.3552 | 0.3514 | 0.155* | 0.604 (14) |
C2A | 0.5588 (15) | 1.200 (4) | 0.331 (2) | 0.1031 (4) | 0.396 (14) |
H2A1 | 0.5116 | 1.2214 | 0.2940 | 0.124* | 0.396 (14) |
H2A2 | 0.5925 | 1.2862 | 0.3126 | 0.124* | 0.396 (14) |
C2B | 0.5360 (9) | 1.161 (2) | 0.3648 (15) | 0.1031 (4) | 0.604 (14) |
H2B1 | 0.4971 | 1.2070 | 0.3174 | 0.124* | 0.604 (14) |
H2B2 | 0.5144 | 1.1027 | 0.4198 | 0.124* | 0.604 (14) |
C3 | 0.5851 (5) | 1.0320 (10) | 0.3049 (8) | 0.0949 (3) | |
C4 | 0.6131 (4) | 0.8970 (10) | 0.3654 (8) | 0.0989 (3) | |
H4A | 0.6092 | 0.8982 | 0.4361 | 0.119* | |
C5 | 0.6462 (5) | 0.7624 (10) | 0.3222 (8) | 0.098 (3) | |
H5 | 0.6627 | 0.6705 | 0.3626 | 0.117* | |
C6 | 0.6547 (4) | 0.7655 (8) | 0.2171 (7) | 0.074 (2) | |
C7 | 0.6292 (4) | 0.9013 (9) | 0.1591 (8) | 0.093 (3) | |
H7 | 0.6354 | 0.9057 | 0.0891 | 0.111* | |
C8 | 0.5942 (4) | 1.0323 (9) | 0.2052 (7) | 0.0876 (3) | |
H8 | 0.5766 | 1.1232 | 0.1648 | 0.105* | |
C9 | 0.7394 (3) | 0.3735 (7) | 0.1700 (5) | 0.0513 (14) | |
C10 | 0.7604 (3) | 0.2391 (7) | 0.2308 (5) | 0.0559 (15) | |
H10 | 0.7448 | 0.2329 | 0.2965 | 0.067* | |
C11 | 0.8045 (3) | 0.1101 (7) | 0.1984 (4) | 0.0504 (14) | |
C12 | 0.8252 (3) | 0.1123 (7) | 0.0960 (4) | 0.0489 (14) | |
C13 | 0.8007 (4) | 0.2521 (8) | 0.0339 (5) | 0.0707 (19) | |
H13 | 0.8135 | 0.2580 | −0.0334 | 0.085* | |
C14 | 0.7599 (3) | 0.3765 (8) | 0.0685 (5) | 0.0635 (17) | |
H14 | 0.7449 | 0.4658 | 0.0249 | 0.076* | |
C15 | 0.8328 (3) | −0.0110 (7) | 0.2720 (5) | 0.0565 (15) | |
H15 | 0.8160 | −0.0086 | 0.3371 | 0.068* | |
C16 | 0.9197 (3) | −0.2418 (6) | 0.3291 (4) | 0.0463 (13) | |
C17 | 0.9191 (4) | −0.1766 (7) | 0.4412 (5) | 0.0613 (17) | |
H17A | 0.9515 | −0.2468 | 0.4862 | 0.074* | |
H17B | 0.9383 | −0.0622 | 0.4448 | 0.074* | |
C18 | 0.8815 (3) | −0.4126 (6) | 0.3149 (5) | 0.0525 (15) | |
H18A | 0.8317 | −0.4018 | 0.3320 | 0.063* | |
H18B | 0.8802 | −0.4468 | 0.2432 | 0.063* | |
C19 | 0.9975 (3) | −0.2505 (8) | 0.3034 (5) | 0.0594 (16) | |
H19A | 1.0215 | −0.1433 | 0.3197 | 0.071* | |
H19B | 1.0233 | −0.3379 | 0.3447 | 0.071* | |
N1 | 0.6890 (3) | 0.6339 (7) | 0.1643 (5) | 0.0746 (16) | |
N2 | 0.7006 (3) | 0.5033 (7) | 0.2180 (5) | 0.0658 (15) | |
N3 | 0.8805 (3) | −0.1247 (6) | 0.2540 (4) | 0.0484 (12) | |
O1 | 0.8664 (2) | −0.0040 (5) | 0.0630 (3) | 0.0576 (11) | |
O2 | 0.9996 (2) | −0.2874 (5) | 0.1966 (3) | 0.0623 (12) | |
O3 | 0.9180 (3) | −0.5395 (5) | 0.3787 (3) | 0.0620 (12) | |
O4 | 0.8506 (3) | −0.1763 (5) | 0.4778 (3) | 0.0724 (13) | |
H2 | 1.033 (3) | −0.221 (8) | 0.186 (7) | 0.109* | |
H3 | 0.903 (4) | −0.527 (11) | 0.437 (3) | 0.109* | |
H3A | 0.899 (4) | −0.136 (9) | 0.191 (6) | 0.087* | |
H4 | 0.847 (4) | −0.275 (4) | 0.498 (6) | 0.109* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.107 | 0.105 | 0.100 | 0.026 (4) | 0.026 (6) | −0.026 (5) |
C1B | 0.107 | 0.105 | 0.100 | 0.026 (4) | 0.026 (6) | −0.026 (5) |
C2A | 0.107 | 0.105 | 0.100 | 0.026 (4) | 0.026 (6) | −0.026 (5) |
C2B | 0.107 | 0.105 | 0.100 | 0.026 (4) | 0.026 (6) | −0.026 (5) |
C3 | 0.102 | 0.071 | 0.108 | 0.026 (4) | −0.009 (5) | −0.027 (5) |
C4 | 0.102 | 0.085 | 0.108 | 0.026 (5) | 0.004 (5) | −0.013 (5) |
C5 | 0.115 (6) | 0.066 (5) | 0.112 (8) | 0.040 (5) | 0.010 (5) | −0.009 (5) |
C6 | 0.073 (4) | 0.053 (4) | 0.094 (6) | 0.006 (3) | 0.005 (4) | −0.010 (4) |
C7 | 0.091 (5) | 0.056 (4) | 0.127 (8) | −0.003 (4) | −0.009 (5) | 0.009 (5) |
C8 | 0.090 | 0.060 | 0.109 | 0.014 (4) | −0.007 (5) | −0.006 (5) |
C9 | 0.059 (4) | 0.039 (3) | 0.056 (4) | 0.006 (3) | 0.004 (3) | −0.005 (3) |
C10 | 0.067 (4) | 0.050 (3) | 0.051 (4) | 0.005 (3) | 0.008 (3) | −0.001 (3) |
C11 | 0.060 (4) | 0.046 (3) | 0.044 (3) | −0.003 (3) | 0.001 (3) | 0.003 (3) |
C12 | 0.063 (4) | 0.043 (3) | 0.041 (3) | −0.002 (3) | 0.004 (3) | −0.001 (3) |
C13 | 0.102 (5) | 0.064 (4) | 0.047 (4) | 0.016 (4) | 0.014 (3) | 0.014 (3) |
C14 | 0.077 (4) | 0.051 (4) | 0.061 (4) | 0.008 (3) | −0.002 (3) | 0.011 (3) |
C15 | 0.073 (4) | 0.053 (4) | 0.044 (3) | 0.004 (3) | 0.009 (3) | 0.006 (3) |
C16 | 0.067 (4) | 0.038 (3) | 0.033 (3) | 0.000 (3) | 0.002 (2) | 0.006 (2) |
C17 | 0.094 (5) | 0.040 (3) | 0.047 (4) | 0.001 (3) | −0.005 (3) | −0.001 (3) |
C18 | 0.076 (4) | 0.039 (3) | 0.043 (3) | −0.005 (3) | 0.008 (3) | −0.001 (2) |
C19 | 0.064 (4) | 0.048 (3) | 0.065 (5) | −0.010 (3) | 0.004 (3) | 0.012 (3) |
N1 | 0.083 (4) | 0.065 (4) | 0.074 (4) | 0.006 (3) | 0.000 (3) | 0.003 (3) |
N2 | 0.061 (3) | 0.053 (3) | 0.081 (4) | 0.006 (3) | 0.000 (3) | 0.005 (3) |
N3 | 0.062 (3) | 0.042 (3) | 0.041 (3) | 0.006 (2) | 0.004 (2) | 0.002 (2) |
O1 | 0.081 (3) | 0.054 (2) | 0.038 (2) | 0.006 (2) | 0.0093 (18) | −0.0019 (19) |
O2 | 0.082 (3) | 0.051 (3) | 0.055 (3) | −0.007 (2) | 0.017 (2) | −0.002 (2) |
O3 | 0.103 (3) | 0.037 (2) | 0.049 (3) | 0.009 (2) | 0.019 (2) | 0.0068 (19) |
O4 | 0.116 (4) | 0.058 (3) | 0.047 (3) | 0.019 (3) | 0.025 (2) | 0.007 (2) |
Geometric parameters (Å, º) top
C1A—C2A | 1.58 (4) | C10—H10 | 0.9300 |
C1A—H1A1 | 0.9600 | C11—C15 | 1.416 (8) |
C1A—H1A2 | 0.9600 | C11—C12 | 1.421 (8) |
C1A—H1A3 | 0.9600 | C12—O1 | 1.292 (7) |
C1B—C2B | 1.44 (2) | C12—C13 | 1.416 (8) |
C1B—H1B1 | 0.9600 | C13—C14 | 1.342 (9) |
C1B—H1B2 | 0.9600 | C13—H13 | 0.9300 |
C1B—H1B3 | 0.9600 | C14—H14 | 0.9300 |
C2A—C3 | 1.46 (3) | C15—N3 | 1.295 (7) |
C2A—H2A1 | 0.9700 | C15—H15 | 0.9300 |
C2A—H2A2 | 0.9700 | C16—N3 | 1.482 (7) |
C2B—C3 | 1.614 (18) | C16—C19 | 1.506 (8) |
C2B—H2B1 | 0.9700 | C16—C18 | 1.525 (7) |
C2B—H2B2 | 0.9700 | C16—C17 | 1.548 (8) |
C3—C8 | 1.324 (12) | C17—O4 | 1.392 (8) |
C3—C4 | 1.394 (12) | C17—H17A | 0.9700 |
C4—C5 | 1.373 (11) | C17—H17B | 0.9700 |
C4—H4A | 0.9300 | C18—O3 | 1.428 (7) |
C5—C6 | 1.391 (12) | C18—H18A | 0.9700 |
C5—H5 | 0.9300 | C18—H18B | 0.9700 |
C6—C7 | 1.368 (10) | C19—O2 | 1.425 (7) |
C6—N1 | 1.428 (9) | C19—H19A | 0.9700 |
C7—C8 | 1.386 (11) | C19—H19B | 0.9700 |
C7—H7 | 0.9300 | N1—N2 | 1.253 (7) |
C8—H8 | 0.9300 | N3—H3A | 0.93 (8) |
C9—C10 | 1.357 (8) | O2—H2 | 0.83 (2) |
C9—C14 | 1.409 (9) | O3—H3 | 0.84 (2) |
C9—N2 | 1.428 (8) | O4—H4 | 0.82 (2) |
C10—C11 | 1.394 (8) | | |
| | | |
C2B—C1B—H1B1 | 109.5 | C10—C11—C12 | 119.4 (5) |
C2B—C1B—H1B2 | 109.5 | C15—C11—C12 | 121.9 (5) |
H1B1—C1B—H1B2 | 109.5 | O1—C12—C13 | 122.0 (6) |
C2B—C1B—H1B3 | 109.5 | O1—C12—C11 | 121.5 (5) |
H1B1—C1B—H1B3 | 109.5 | C13—C12—C11 | 116.4 (6) |
H1B2—C1B—H1B3 | 109.5 | C14—C13—C12 | 122.5 (6) |
C3—C2A—C1A | 108 (2) | C14—C13—H13 | 118.7 |
C3—C2A—H2A1 | 110.0 | C12—C13—H13 | 118.7 |
C1A—C2A—H2A1 | 110.0 | C13—C14—C9 | 120.8 (6) |
C3—C2A—H2A2 | 110.0 | C13—C14—H14 | 119.6 |
C1A—C2A—H2A2 | 110.0 | C9—C14—H14 | 119.6 |
H2A1—C2A—H2A2 | 108.4 | N3—C15—C11 | 124.0 (6) |
C1B—C2B—C3 | 108.0 (13) | N3—C15—H15 | 118.0 |
C1B—C2B—H2B1 | 110.1 | C11—C15—H15 | 118.0 |
C3—C2B—H2B1 | 110.1 | N3—C16—C19 | 107.3 (5) |
C1B—C2B—H2B2 | 110.1 | N3—C16—C18 | 106.4 (4) |
C3—C2B—H2B2 | 110.1 | C19—C16—C18 | 111.8 (5) |
H2B1—C2B—H2B2 | 108.4 | N3—C16—C17 | 111.5 (5) |
C8—C3—C4 | 118.7 (8) | C19—C16—C17 | 108.5 (5) |
C8—C3—C2A | 107.7 (14) | C18—C16—C17 | 111.3 (5) |
C4—C3—C2A | 132.3 (14) | O4—C17—C16 | 114.3 (5) |
C8—C3—C2B | 127.0 (10) | O4—C17—H17A | 108.7 |
C4—C3—C2B | 113.9 (11) | C16—C17—H17A | 108.7 |
C2A—C3—C2B | 25.8 (11) | O4—C17—H17B | 108.7 |
C5—C4—C3 | 121.1 (10) | C16—C17—H17B | 108.7 |
C5—C4—H4A | 119.5 | H17A—C17—H17B | 107.6 |
C3—C4—H4A | 119.5 | O3—C18—C16 | 111.4 (5) |
C4—C5—C6 | 119.0 (8) | O3—C18—H18A | 109.4 |
C4—C5—H5 | 120.5 | C16—C18—H18A | 109.4 |
C6—C5—H5 | 120.5 | O3—C18—H18B | 109.4 |
C7—C6—C5 | 119.4 (7) | C16—C18—H18B | 109.4 |
C7—C6—N1 | 116.7 (8) | H18A—C18—H18B | 108.0 |
C5—C6—N1 | 123.9 (6) | O2—C19—C16 | 110.0 (4) |
C6—C7—C8 | 119.7 (9) | O2—C19—H19A | 109.7 |
C6—C7—H7 | 120.1 | C16—C19—H19A | 109.7 |
C8—C7—H7 | 120.1 | O2—C19—H19B | 109.7 |
C3—C8—C7 | 122.0 (8) | C16—C19—H19B | 109.7 |
C3—C8—H8 | 119.0 | H19A—C19—H19B | 108.2 |
C7—C8—H8 | 119.0 | N2—N1—C6 | 113.0 (6) |
C10—C9—C14 | 118.2 (5) | N1—N2—C9 | 114.4 (6) |
C10—C9—N2 | 115.7 (6) | C15—N3—C16 | 127.7 (5) |
C14—C9—N2 | 126.0 (5) | C15—N3—H3A | 123 (4) |
C9—C10—C11 | 122.5 (6) | C16—N3—H3A | 109 (4) |
C9—C10—H10 | 118.7 | C19—O2—H2 | 97 (6) |
C11—C10—H10 | 118.7 | C18—O3—H3 | 106 (6) |
C10—C11—C15 | 118.5 (6) | C17—O4—H4 | 102 (6) |
| | | |
C1A—C2A—C3—C8 | −176.5 (17) | O1—C12—C13—C14 | −177.8 (6) |
C1A—C2A—C3—C4 | −10 (3) | C11—C12—C13—C14 | −0.4 (9) |
C1A—C2A—C3—C2B | 41 (3) | C12—C13—C14—C9 | 0.2 (10) |
C1B—C2B—C3—C8 | −94.3 (16) | C10—C9—C14—C13 | −1.8 (9) |
C1B—C2B—C3—C4 | 93.4 (16) | N2—C9—C14—C13 | 175.3 (6) |
C1B—C2B—C3—C2A | −47 (3) | C10—C11—C15—N3 | −172.0 (5) |
C8—C3—C4—C5 | −3.3 (13) | C12—C11—C15—N3 | 2.2 (9) |
C2A—C3—C4—C5 | −168.4 (17) | N3—C16—C17—O4 | 67.3 (6) |
C2B—C3—C4—C5 | 169.7 (10) | C19—C16—C17—O4 | −174.8 (5) |
C3—C4—C5—C6 | 2.9 (13) | C18—C16—C17—O4 | −51.4 (6) |
C4—C5—C6—C7 | −0.7 (12) | N3—C16—C18—O3 | 175.9 (5) |
C4—C5—C6—N1 | 179.2 (7) | C19—C16—C18—O3 | 59.1 (6) |
C5—C6—C7—C8 | −1.2 (11) | C17—C16—C18—O3 | −62.4 (6) |
N1—C6—C7—C8 | 178.9 (6) | N3—C16—C19—O2 | −51.4 (6) |
C4—C3—C8—C7 | 1.3 (13) | C18—C16—C19—O2 | 64.9 (6) |
C2A—C3—C8—C7 | 169.8 (14) | C17—C16—C19—O2 | −172.0 (4) |
C2B—C3—C8—C7 | −170.7 (11) | C7—C6—N1—N2 | −169.6 (6) |
C6—C7—C8—C3 | 0.9 (12) | C5—C6—N1—N2 | 10.5 (10) |
C14—C9—C10—C11 | 3.7 (9) | C6—N1—N2—C9 | −175.9 (5) |
N2—C9—C10—C11 | −173.8 (5) | C10—C9—N2—N1 | 172.4 (5) |
C9—C10—C11—C15 | 170.5 (5) | C14—C9—N2—N1 | −4.8 (8) |
C9—C10—C11—C12 | −3.8 (8) | C11—C15—N3—C16 | 171.8 (5) |
C10—C11—C12—O1 | 179.5 (5) | C19—C16—N3—C15 | −138.9 (6) |
C15—C11—C12—O1 | 5.4 (8) | C18—C16—N3—C15 | 101.3 (6) |
C10—C11—C12—C13 | 2.0 (8) | C17—C16—N3—C15 | −20.2 (8) |
C15—C11—C12—C13 | −172.1 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3i | 0.83 (2) | 1.93 (4) | 2.718 (6) | 158 (8) |
O3—H3···O1ii | 0.84 (2) | 1.85 (2) | 2.685 (6) | 177 (8) |
N3—H3A···O1 | 0.93 (8) | 2.00 (7) | 2.652 (6) | 125 (6) |
N3—H3A···O2 | 0.93 (8) | 2.20 (7) | 2.712 (7) | 114 (5) |
O4—H4···O1ii | 0.82 (2) | 1.96 (3) | 2.762 (6) | 163 (8) |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) x, −y−1/2, z+1/2. |