On heating
N′-benzoyl-7-hydroxy-6-hexyl-2-oxo-2
H-chromene-3-carbohydrazonamide in dimethylformamide, the process of cyclization leads to the formation of a triazole derivative of a 3-substituted chromenone, C
23H
23N
3O
3·H
2O, as confirmed by this crystal structure investigation. The three ring systems are almost coplanar and, in the crystal structure, a three-dimensional network of hydrogen bonds is formed; these are of the types O—H
O, N—H
N, O—H
N and C—H
O.
Supporting information
CCDC reference: 248846
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.099
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C2 .. 7.35 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for O2 - C2 .. 12.36 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C8 .. 10.60 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C12 .. 10.70 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C11 .. 10.62 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for N3 - C12 .. 8.03 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C13 - C14 .. 12.80 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C13 - C18 .. 15.08 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 - C15 .. 8.28 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C15 - C16 .. 12.48 su
Alert level C
PLAT126_ALERT_1_C Error in or Uninterpretable Hall Symbol ....... -1 P
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl .... -1 p
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.28 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.70 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.10 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C19 .. 5.12 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.27 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 6.23 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C19 - C20 .. 6.51 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
0 ALERT level A = In general: serious problem
10 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
16 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
Data collection: P3 (Siemens,1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991) and XPREP (Siemens, 1991); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C23H23N3O3·H2O | Z = 2 |
Mr = 407.46 | F(000) = 432 |
Triclinic, P1 | Dx = 1.252 Mg m−3 |
Hall symbol: -1 P | Mo Kα radiation, λ = 0.71073 Å |
a = 9.465 (2) Å | Cell parameters from 24 reflections |
b = 10.316 (2) Å | θ = 11.0–12.0° |
c = 12.518 (3) Å | µ = 0.09 mm−1 |
α = 79.521 (17)° | T = 293 K |
β = 88.450 (17)° | Block, light yellow |
γ = 64.259 (17)° | 0.45 × 0.2 × 0.15 mm |
V = 1080.7 (4) Å3 | |
Data collection top
Siemens P3/PC diffractometer | θmax = 25.5°, θmin = 2.8° |
2θ/θ scans | h = −10→11 |
4168 measured reflections | k = −10→12 |
3991 independent reflections | l = 0→14 |
2430 reflections with I > 2σ(I) | 2 standard reflections every 98 reflections |
Rint = 0.073 | intensity decay: 1% |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0345P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.13 e Å−3 |
3991 reflections | Δρmin = −0.13 e Å−3 |
272 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.07997 (10) | 0.75071 (10) | 0.42661 (8) | 0.0486 (3) | |
O2 | −0.27383 (11) | 0.70592 (11) | 0.49664 (9) | 0.0613 (3) | |
O3 | 0.32411 (11) | 0.87554 (11) | 0.28299 (10) | 0.0723 (3) | |
H3 | 0.2655 | 0.969 | 0.2945 | 0.087* | |
N1 | −0.17197 (12) | 0.35116 (12) | 0.33385 (10) | 0.0479 (3) | |
N2 | −0.33907 (12) | 0.49022 (12) | 0.43667 (10) | 0.0493 (3) | |
H2 | −0.3821 | 0.5581 | 0.4743 | 0.059* | |
N3 | −0.39466 (12) | 0.39132 (13) | 0.42375 (10) | 0.0501 (3) | |
C2 | −0.16616 (15) | 0.67153 (15) | 0.43574 (12) | 0.0487 (4) | |
C3 | −0.11732 (15) | 0.55305 (15) | 0.37428 (11) | 0.0454 (4) | |
C4 | 0.00869 (15) | 0.52392 (15) | 0.31310 (12) | 0.0479 (4) | |
H4 | 0.0384 | 0.4481 | 0.2745 | 0.058* | |
C5 | 0.09704 (15) | 0.60629 (15) | 0.30632 (12) | 0.0465 (4) | |
C6 | 0.23119 (16) | 0.58224 (16) | 0.24616 (13) | 0.0553 (4) | |
H6 | 0.268 | 0.5044 | 0.2091 | 0.066* | |
C7 | 0.31121 (16) | 0.66795 (16) | 0.23918 (12) | 0.0515 (4) | |
C8 | 0.24939 (16) | 0.78788 (16) | 0.29472 (12) | 0.0512 (4) | |
C9 | 0.12005 (15) | 0.81336 (15) | 0.35696 (12) | 0.0475 (4) | |
H9 | 0.0832 | 0.8904 | 0.3948 | 0.057* | |
C10 | 0.04711 (14) | 0.72305 (14) | 0.36188 (11) | 0.0429 (4) | |
C11 | −0.20813 (15) | 0.46701 (15) | 0.38265 (12) | 0.0451 (4) | |
C12 | −0.28923 (15) | 0.31064 (15) | 0.36096 (11) | 0.0442 (4) | |
C13 | −0.30498 (15) | 0.19117 (15) | 0.32083 (12) | 0.0465 (4) | |
C14 | −0.41359 (18) | 0.14165 (18) | 0.36463 (16) | 0.0684 (5) | |
H14 | −0.4728 | 0.1808 | 0.4212 | 0.082* | |
C15 | −0.4337 (2) | 0.0324 (2) | 0.32320 (18) | 0.0840 (6) | |
H15 | −0.505 | −0.0022 | 0.3526 | 0.101* | |
C16 | −0.3465 (2) | −0.0223 (2) | 0.23880 (15) | 0.0750 (5) | |
H16 | −0.3629 | −0.0917 | 0.2095 | 0.09* | |
C17 | −0.2374 (2) | 0.02122 (19) | 0.19664 (15) | 0.0719 (5) | |
H17 | −0.1771 | −0.02 | 0.1411 | 0.086* | |
C18 | −0.21703 (19) | 0.12949 (18) | 0.23839 (14) | 0.0646 (5) | |
H18 | −0.1426 | 0.1603 | 0.2098 | 0.077* | |
C19 | 0.45558 (17) | 0.63683 (17) | 0.17444 (13) | 0.0603 (5) | |
H19A | 0.5096 | 0.5325 | 0.1745 | 0.09* | |
H19B | 0.5264 | 0.664 | 0.2092 | 0.09* | |
C20 | 0.4156 (2) | 0.7199 (2) | 0.05761 (15) | 0.0748 (6) | |
H20A | 0.3702 | 0.8243 | 0.0575 | 0.112* | |
H20B | 0.3372 | 0.6998 | 0.0251 | 0.112* | |
C21 | 0.5617 (2) | 0.6779 (2) | −0.01296 (16) | 0.0785 (6) | |
H21A | 0.6171 | 0.572 | −0.0026 | 0.118* | |
H21B | 0.5259 | 0.7148 | −0.0891 | 0.118* | |
C22 | 0.6752 (2) | 0.7371 (2) | 0.01348 (17) | 0.0898 (6) | |
H22A | 0.7179 | 0.6943 | 0.0879 | 0.135* | |
H22B | 0.6186 | 0.8423 | 0.0082 | 0.135* | |
C23 | 0.8102 (2) | 0.7038 (3) | −0.06264 (19) | 0.1041 (7) | |
H23A | 0.8669 | 0.5984 | −0.0568 | 0.156* | |
H23B | 0.767 | 0.7455 | −0.137 | 0.156* | |
C24 | 0.9241 (3) | 0.7630 (3) | −0.0388 (2) | 0.1404 (10) | |
H24A | 0.8789 | 0.8667 | −0.0661 | 0.211* | |
H24B | 1.02 | 0.7157 | −0.0735 | 0.211* | |
H24C | 0.9459 | 0.7442 | 0.0384 | 0.211* | |
O4 | 0.16083 (13) | 1.12383 (13) | 0.36105 (11) | 0.0876 (4) | |
H4A | 0.0619 | 1.1902 | 0.3427 | 0.105* | |
H4B | 0.2018 | 1.1718 | 0.3913 | 0.105* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0463 (5) | 0.0535 (5) | 0.0567 (6) | −0.0284 (4) | 0.0187 (4) | −0.0207 (4) |
O2 | 0.0554 (5) | 0.0688 (6) | 0.0715 (7) | −0.0338 (5) | 0.0330 (5) | −0.0281 (5) |
O3 | 0.0672 (5) | 0.0682 (6) | 0.1109 (9) | −0.0485 (5) | 0.0341 (6) | −0.0422 (6) |
N1 | 0.0408 (5) | 0.0598 (7) | 0.0537 (7) | −0.0299 (5) | 0.0133 (5) | −0.0170 (5) |
N2 | 0.0421 (5) | 0.0546 (6) | 0.0611 (7) | −0.0266 (5) | 0.0194 (5) | −0.0223 (5) |
N3 | 0.0465 (5) | 0.0558 (6) | 0.0600 (8) | −0.0324 (5) | 0.0115 (5) | −0.0143 (5) |
C2 | 0.0445 (7) | 0.0506 (8) | 0.0520 (9) | −0.0219 (6) | 0.0065 (7) | −0.0094 (7) |
C3 | 0.0429 (7) | 0.0497 (7) | 0.0474 (8) | −0.0230 (6) | 0.0064 (6) | −0.0115 (6) |
C4 | 0.0502 (7) | 0.0496 (8) | 0.0489 (8) | −0.0250 (6) | 0.0085 (6) | −0.0134 (6) |
C5 | 0.0477 (7) | 0.0475 (7) | 0.0483 (8) | −0.0239 (6) | 0.0069 (6) | −0.0108 (6) |
C6 | 0.0538 (8) | 0.0544 (8) | 0.0628 (10) | −0.0254 (7) | 0.0126 (7) | −0.0198 (7) |
C7 | 0.0489 (7) | 0.0532 (8) | 0.0534 (9) | −0.0232 (6) | 0.0083 (7) | −0.0114 (7) |
C8 | 0.0489 (7) | 0.0520 (8) | 0.0566 (9) | −0.0254 (6) | 0.0046 (7) | −0.0112 (7) |
C9 | 0.0481 (7) | 0.0504 (8) | 0.0477 (8) | −0.0231 (6) | 0.0075 (6) | −0.0146 (6) |
C10 | 0.0402 (6) | 0.0434 (7) | 0.0468 (8) | −0.0196 (6) | 0.0071 (6) | −0.0099 (6) |
C11 | 0.0420 (7) | 0.0480 (7) | 0.0475 (8) | −0.0216 (6) | 0.0047 (6) | −0.0091 (6) |
C12 | 0.0407 (7) | 0.0469 (7) | 0.0443 (8) | −0.0188 (6) | 0.0041 (6) | −0.0079 (6) |
C13 | 0.0444 (7) | 0.0502 (8) | 0.0478 (8) | −0.0234 (6) | 0.0071 (6) | −0.0095 (6) |
C14 | 0.0612 (9) | 0.0641 (9) | 0.0886 (13) | −0.0322 (8) | 0.0149 (9) | −0.0244 (9) |
C15 | 0.0694 (10) | 0.0734 (11) | 0.1172 (17) | −0.0379 (9) | 0.0037 (11) | −0.0193 (11) |
C16 | 0.0816 (11) | 0.0728 (11) | 0.0764 (13) | −0.0365 (9) | −0.0042 (10) | −0.0194 (9) |
C17 | 0.0804 (11) | 0.0699 (10) | 0.0695 (12) | −0.0343 (9) | 0.0070 (9) | −0.0193 (9) |
C18 | 0.0689 (9) | 0.0651 (10) | 0.0642 (11) | −0.0320 (8) | 0.0033 (8) | −0.0156 (8) |
C19 | 0.0569 (8) | 0.0637 (9) | 0.0637 (10) | −0.0297 (7) | 0.0108 (8) | −0.0122 (8) |
C20 | 0.0696 (10) | 0.0776 (11) | 0.0738 (12) | −0.0302 (9) | 0.0078 (9) | −0.0122 (9) |
C21 | 0.0764 (11) | 0.0823 (12) | 0.0805 (13) | −0.0367 (9) | 0.0188 (10) | −0.0208 (10) |
C22 | 0.0894 (12) | 0.1020 (14) | 0.0900 (14) | −0.0487 (11) | 0.0253 (11) | −0.0313 (11) |
C23 | 0.0942 (13) | 0.1340 (17) | 0.0971 (16) | −0.0584 (12) | 0.0281 (12) | −0.0336 (13) |
C24 | 0.1285 (18) | 0.167 (2) | 0.162 (3) | −0.0894 (16) | 0.0384 (17) | −0.0567 (19) |
O4 | 0.0608 (7) | 0.0885 (7) | 0.1263 (10) | −0.0267 (6) | 0.0109 (7) | −0.0673 (7) |
Geometric parameters (Å, º) top
O1—C2 | 1.3730 (17) | C14—H14 | 0.93 |
O1—C10 | 1.3849 (15) | C15—C16 | 1.371 (3) |
O2—C2 | 1.2198 (16) | C15—H15 | 0.93 |
O3—C8 | 1.3569 (18) | C16—C17 | 1.355 (3) |
O3—H3 | 0.9168 | C16—H16 | 0.93 |
N1—C11 | 1.3481 (18) | C17—C18 | 1.401 (2) |
N1—C12 | 1.3612 (17) | C17—H17 | 0.93 |
N2—C11 | 1.3440 (16) | C18—H18 | 0.93 |
N2—N3 | 1.3692 (17) | C19—C20 | 1.520 (2) |
N2—H2 | 0.86 | C19—H19A | 0.97 |
N3—C12 | 1.3343 (17) | C19—H19B | 0.97 |
C2—C3 | 1.460 (2) | C20—C21 | 1.560 (2) |
C3—C4 | 1.3500 (18) | C20—H20A | 0.97 |
C3—C11 | 1.470 (2) | C20—H20B | 0.97 |
C4—C5 | 1.420 (2) | C21—C22 | 1.516 (3) |
C4—H4 | 0.93 | C21—H21A | 0.97 |
C5—C10 | 1.397 (2) | C21—H21B | 0.97 |
C5—C6 | 1.4083 (19) | C22—C23 | 1.527 (3) |
C6—C7 | 1.383 (2) | C22—H22A | 0.97 |
C6—H6 | 0.93 | C22—H22B | 0.97 |
C7—C8 | 1.421 (2) | C23—C24 | 1.510 (3) |
C7—C19 | 1.510 (2) | C23—H23A | 0.97 |
C8—C9 | 1.3849 (19) | C23—H23B | 0.97 |
C9—C10 | 1.373 (2) | C24—H24A | 0.96 |
C9—H9 | 0.93 | C24—H24B | 0.96 |
C12—C13 | 1.477 (2) | C24—H24C | 0.96 |
C13—C18 | 1.377 (2) | O4—H4A | 0.8918 |
C13—C14 | 1.394 (2) | O4—H4B | 0.8846 |
C14—C15 | 1.408 (3) | | |
| | | |
C2—O1—C10 | 122.81 (11) | C14—C15—H15 | 120.6 |
C8—O3—H3 | 115.7 | C17—C16—C15 | 122.25 (19) |
C11—N1—C12 | 103.24 (11) | C17—C16—H16 | 118.9 |
C11—N2—N3 | 110.89 (12) | C15—C16—H16 | 118.9 |
C11—N2—H2 | 124.6 | C16—C17—C18 | 118.68 (17) |
N3—N2—H2 | 124.6 | C16—C17—H17 | 120.7 |
C12—N3—N2 | 101.89 (11) | C18—C17—H17 | 120.7 |
O2—C2—O1 | 116.17 (13) | C13—C18—C17 | 121.34 (16) |
O2—C2—C3 | 126.82 (14) | C13—C18—H18 | 119.3 |
O1—C2—C3 | 116.99 (12) | C17—C18—H18 | 119.3 |
C4—C3—C2 | 120.23 (14) | C7—C19—C20 | 112.21 (13) |
C4—C3—C11 | 121.84 (14) | C7—C19—H19A | 109.2 |
C2—C3—C11 | 117.93 (12) | C20—C19—H19A | 109.2 |
C3—C4—C5 | 121.60 (14) | C7—C19—H19B | 109.2 |
C3—C4—H4 | 119.2 | C20—C19—H19B | 109.2 |
C5—C4—H4 | 119.2 | H19A—C19—H19B | 107.9 |
C10—C5—C6 | 116.27 (14) | C19—C20—C21 | 112.71 (14) |
C10—C5—C4 | 118.23 (12) | C19—C20—H20A | 109 |
C6—C5—C4 | 125.49 (14) | C21—C20—H20A | 109 |
C7—C6—C5 | 123.62 (14) | C19—C20—H20B | 109 |
C7—C6—H6 | 118.2 | C21—C20—H20B | 109 |
C5—C6—H6 | 118.2 | H20A—C20—H20B | 107.8 |
C6—C7—C8 | 116.60 (13) | C22—C21—C20 | 113.84 (17) |
C6—C7—C19 | 121.65 (14) | C22—C21—H21A | 108.8 |
C8—C7—C19 | 121.74 (14) | C20—C21—H21A | 108.8 |
O3—C8—C9 | 122.21 (14) | C22—C21—H21B | 108.8 |
O3—C8—C7 | 116.16 (13) | C20—C21—H21B | 108.8 |
C9—C8—C7 | 121.63 (14) | H21A—C21—H21B | 107.7 |
C10—C9—C8 | 118.91 (14) | C21—C22—C23 | 112.44 (18) |
C10—C9—H9 | 120.5 | C21—C22—H22A | 109.1 |
C8—C9—H9 | 120.5 | C23—C22—H22A | 109.1 |
C9—C10—O1 | 117.05 (12) | C21—C22—H22B | 109.1 |
C9—C10—C5 | 122.90 (12) | C23—C22—H22B | 109.1 |
O1—C10—C5 | 120.05 (13) | H22A—C22—H22B | 107.8 |
N2—C11—N1 | 109.06 (13) | C24—C23—C22 | 113.5 (2) |
N2—C11—C3 | 126.95 (13) | C24—C23—H23A | 108.9 |
N1—C11—C3 | 123.98 (12) | C22—C23—H23A | 108.9 |
N3—C12—N1 | 114.92 (13) | C24—C23—H23B | 108.9 |
N3—C12—C13 | 121.62 (12) | C22—C23—H23B | 108.9 |
N1—C12—C13 | 123.40 (12) | H23A—C23—H23B | 107.7 |
C18—C13—C14 | 118.78 (15) | C23—C24—H24A | 109.5 |
C18—C13—C12 | 121.30 (14) | C23—C24—H24B | 109.5 |
C14—C13—C12 | 119.89 (13) | H24A—C24—H24B | 109.5 |
C13—C14—C15 | 119.99 (16) | C23—C24—H24C | 109.5 |
C13—C14—H14 | 120 | H24A—C24—H24C | 109.5 |
C15—C14—H14 | 120 | H24B—C24—H24C | 109.5 |
C16—C15—C14 | 118.89 (18) | H4A—O4—H4B | 103.4 |
C16—C15—H15 | 120.6 | | |
| | | |
C11—N2—N3—C12 | 0.45 (14) | N3—N2—C11—C3 | 178.00 (13) |
C10—O1—C2—O2 | 179.05 (12) | C12—N1—C11—N2 | 0.89 (14) |
C10—O1—C2—C3 | 0.64 (18) | C12—N1—C11—C3 | −178.03 (13) |
O2—C2—C3—C4 | −177.34 (14) | C4—C3—C11—N2 | −176.68 (14) |
O1—C2—C3—C4 | 0.88 (19) | C2—C3—C11—N2 | 4.1 (2) |
O2—C2—C3—C11 | 1.9 (2) | C4—C3—C11—N1 | 2.1 (2) |
O1—C2—C3—C11 | −179.87 (11) | C2—C3—C11—N1 | −177.19 (13) |
C2—C3—C4—C5 | 0.0 (2) | N2—N3—C12—N1 | 0.14 (15) |
C11—C3—C4—C5 | −179.26 (13) | N2—N3—C12—C13 | −177.24 (12) |
C3—C4—C5—C10 | −2.3 (2) | C11—N1—C12—N3 | −0.65 (15) |
C3—C4—C5—C6 | 178.92 (14) | C11—N1—C12—C13 | 176.68 (13) |
C10—C5—C6—C7 | −0.8 (2) | N3—C12—C13—C18 | 165.86 (14) |
C4—C5—C6—C7 | 178.02 (14) | N1—C12—C13—C18 | −11.3 (2) |
C5—C6—C7—C8 | −1.5 (2) | N3—C12—C13—C14 | −12.4 (2) |
C5—C6—C7—C19 | 179.40 (14) | N1—C12—C13—C14 | 170.45 (14) |
C6—C7—C8—O3 | −176.86 (13) | C18—C13—C14—C15 | −1.1 (2) |
C19—C7—C8—O3 | 2.3 (2) | C12—C13—C14—C15 | 177.18 (15) |
C6—C7—C8—C9 | 3.0 (2) | C13—C14—C15—C16 | −0.8 (3) |
C19—C7—C8—C9 | −177.85 (14) | C14—C15—C16—C17 | 2.6 (3) |
O3—C8—C9—C10 | 177.68 (13) | C15—C16—C17—C18 | −2.3 (3) |
C7—C8—C9—C10 | −2.2 (2) | C14—C13—C18—C17 | 1.5 (2) |
C8—C9—C10—O1 | 178.85 (12) | C12—C13—C18—C17 | −176.83 (14) |
C8—C9—C10—C5 | −0.3 (2) | C16—C17—C18—C13 | 0.2 (2) |
C2—O1—C10—C9 | 177.84 (12) | C6—C7—C19—C20 | 91.41 (18) |
C2—O1—C10—C5 | −2.99 (18) | C8—C7—C19—C20 | −87.68 (19) |
C6—C5—C10—C9 | 1.8 (2) | C7—C19—C20—C21 | −174.75 (15) |
C4—C5—C10—C9 | −177.16 (13) | C19—C20—C21—C22 | −72.5 (2) |
C6—C5—C10—O1 | −177.35 (12) | C20—C21—C22—C23 | −175.70 (16) |
C4—C5—C10—O1 | 3.71 (19) | C21—C22—C23—C24 | 179.39 (18) |
N3—N2—C11—N1 | −0.88 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.92 | 1.81 | 2.701 (2) | 162 |
N2—H2···O2 | 0.86 | 2.23 | 2.779 (2) | 121 |
N2—H2···N3i | 0.86 | 2.35 | 2.960 (2) | 129 |
O4—H4A···N1ii | 0.89 | 2.10 | 2.981 (2) | 168 |
O4—H4B···O2iii | 0.89 | 2.34 | 3.206 (2) | 167 |
C14—H14···O2i | 0.93 | 2.46 | 3.304 (2) | 151 |
Symmetry codes: (i) −x−1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x, −y+2, −z+1. |