The title compound, C
22H
19N
5O
6, is an important intermediate in the synthesis of analogs of the dihydropyridine calcium channel blocker nefidipine. The crystal packing is stabilized by intermolecular N—H
N and C—H
O hydrogen bonds.
Supporting information
CCDC reference: 629672
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.058
- wR factor = 0.147
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 19.20 Deg.
O3 -N2 -O3' 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 37.80 Deg.
O4' -N2 -O4 1.555 1.555 1.555
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
4 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
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: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
3-benzotriazol-1-yl 5-methyl
2,6-dimethyl-4-(
p-nitrophenyl)-1,4-dihydropyridine- 3,5-dicarboxylate
top
Crystal data top
C22H19N5O6 | F(000) = 468 |
Mr = 449.42 | Dx = 1.400 Mg m−3 |
Triclinic, P1 | Melting point: 490-491K K |
a = 10.318 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.751 (2) Å | Cell parameters from 3240 reflections |
c = 11.491 (2) Å | θ = 2.3–25.0° |
α = 64.37 (3)° | µ = 0.11 mm−1 |
β = 76.09 (3)° | T = 293 K |
γ = 68.77 (3)° | Block, yellow |
V = 1065.9 (4) Å3 | 0.10 × 0.08 × 0.06 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area detector diffractometer | 3740 independent reflections |
Radiation source: fine-focus sealed tube | 2226 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.0°, θmin = 2.1° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→7 |
Tmin = 0.990, Tmax = 0.994 | l = −13→12 |
6615 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)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.0742P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
3740 reflections | Δρmax = 0.28 e Å−3 |
324 parameters | Δρmin = −0.22 e Å−3 |
30 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.041 (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 | Occ. (<1) |
O1 | 0.0592 (2) | 0.96439 (19) | −0.2114 (2) | 0.0644 (6) | |
O2 | 0.0151 (3) | 0.7573 (2) | −0.1349 (3) | 0.1005 (11) | |
O3 | −0.294 (2) | 0.6164 (17) | 0.5304 (19) | 0.081 (6) | 0.36 (2) |
O4 | −0.267 (2) | 0.4134 (16) | 0.5169 (17) | 0.091 (5) | 0.36 (2) |
O3' | −0.2627 (12) | 0.5865 (12) | 0.5530 (10) | 0.069 (2) | 0.64 (2) |
O4' | −0.3286 (10) | 0.4729 (13) | 0.4724 (9) | 0.080 (3) | 0.64 (2) |
O5 | 0.5048 (2) | 0.31643 (17) | 0.19907 (18) | 0.0521 (6) | |
O6 | 0.3018 (2) | 0.33212 (16) | 0.14098 (19) | 0.0538 (6) | |
N1 | 0.3413 (2) | 0.7793 (2) | 0.0730 (2) | 0.0426 (6) | |
H1 | 0.387 (3) | 0.825 (3) | 0.085 (3) | 0.051* | |
N2 | −0.2478 (3) | 0.5351 (3) | 0.4725 (3) | 0.0647 (8) | |
N3 | 0.3498 (2) | 0.1843 (2) | 0.1837 (2) | 0.0471 (6) | |
N4 | 0.3877 (2) | 0.1232 (2) | 0.0964 (2) | 0.0508 (6) | |
N5 | 0.4145 (2) | −0.0166 (2) | 0.1624 (2) | 0.0498 (6) | |
C1 | 0.2425 (3) | 0.8502 (2) | −0.0147 (2) | 0.0378 (6) | |
C2 | 0.1735 (3) | 0.7743 (2) | −0.0301 (2) | 0.0370 (6) | |
C3 | 0.1923 (3) | 0.6155 (2) | 0.0575 (2) | 0.0382 (6) | |
H3 | 0.1907 | 0.5653 | 0.0044 | 0.046* | |
C4 | 0.3337 (3) | 0.5479 (2) | 0.1111 (2) | 0.0372 (6) | |
C5 | 0.3984 (3) | 0.6316 (2) | 0.1237 (2) | 0.0385 (7) | |
C6 | 0.5279 (3) | 0.5798 (3) | 0.1884 (3) | 0.0505 (8) | |
H6A | 0.5584 | 0.6607 | 0.1723 | 0.076* | |
H6B | 0.5999 | 0.5142 | 0.1544 | 0.076* | |
H6C | 0.5087 | 0.5312 | 0.2802 | 0.076* | |
C7 | 0.2283 (3) | 1.0090 (2) | −0.0835 (3) | 0.0528 (8) | |
H7A | 0.2865 | 1.0254 | −0.1644 | 0.079* | |
H7B | 0.2566 | 1.0411 | −0.0302 | 0.079* | |
H7C | 0.1327 | 1.0617 | −0.0998 | 0.079* | |
C8 | 0.0766 (3) | 0.8286 (3) | −0.1277 (3) | 0.0488 (7) | |
C9 | −0.0323 (4) | 1.0128 (4) | −0.3108 (4) | 0.0884 (13) | |
H9A | −0.0077 | 0.9415 | −0.3477 | 0.133* | |
H9B | −0.0221 | 1.1024 | −0.3775 | 0.133* | |
H9C | −0.1275 | 1.0267 | −0.2728 | 0.133* | |
C10 | 0.0737 (3) | 0.5973 (2) | 0.1656 (2) | 0.0372 (6) | |
C11 | 0.0425 (3) | 0.6650 (3) | 0.2520 (3) | 0.0480 (7) | |
H11 | 0.0944 | 0.7245 | 0.2422 | 0.058* | |
C12 | −0.0624 (3) | 0.6469 (3) | 0.3515 (3) | 0.0504 (8) | |
H12 | −0.0824 | 0.6937 | 0.4082 | 0.060* | |
C13 | −0.1373 (3) | 0.5576 (3) | 0.3650 (3) | 0.0471 (7) | |
C14 | −0.1100 (3) | 0.4880 (3) | 0.2829 (3) | 0.0636 (9) | |
H14 | −0.1612 | 0.4274 | 0.2942 | 0.076* | |
C15 | −0.0046 (3) | 0.5094 (3) | 0.1823 (3) | 0.0569 (8) | |
H15 | 0.0137 | 0.4636 | 0.1250 | 0.068* | |
C16 | 0.3963 (3) | 0.3934 (2) | 0.1560 (2) | 0.0413 (7) | |
C17 | 0.3483 (3) | 0.0875 (3) | 0.3080 (3) | 0.0455 (7) | |
C18 | 0.3153 (4) | 0.0979 (3) | 0.4279 (3) | 0.0713 (10) | |
H18 | 0.2858 | 0.1858 | 0.4376 | 0.086* | |
C19 | 0.3295 (5) | −0.0318 (4) | 0.5316 (3) | 0.0867 (12) | |
H19 | 0.3096 | −0.0322 | 0.6151 | 0.104* | |
C20 | 0.3722 (4) | −0.1616 (4) | 0.5161 (4) | 0.0811 (11) | |
H20 | 0.3788 | −0.2460 | 0.5898 | 0.097* | |
C21 | 0.4045 (4) | −0.1716 (3) | 0.3998 (3) | 0.0640 (9) | |
H21 | 0.4336 | −0.2601 | 0.3913 | 0.077* | |
C22 | 0.3921 (3) | −0.0417 (2) | 0.2919 (3) | 0.0455 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0782 (16) | 0.0502 (11) | 0.0648 (15) | −0.0272 (10) | −0.0343 (13) | −0.0012 (10) |
O2 | 0.156 (3) | 0.0575 (13) | 0.112 (2) | −0.0492 (14) | −0.080 (2) | −0.0049 (13) |
O3 | 0.069 (8) | 0.075 (7) | 0.094 (9) | −0.025 (6) | 0.016 (6) | −0.038 (6) |
O4 | 0.091 (9) | 0.092 (6) | 0.098 (8) | −0.062 (6) | 0.021 (6) | −0.031 (5) |
O3' | 0.068 (5) | 0.073 (4) | 0.063 (4) | −0.023 (3) | 0.018 (3) | −0.034 (3) |
O4' | 0.071 (4) | 0.092 (5) | 0.089 (4) | −0.057 (4) | 0.015 (3) | −0.031 (3) |
O5 | 0.0528 (12) | 0.0384 (9) | 0.0556 (13) | −0.0077 (9) | −0.0096 (10) | −0.0118 (9) |
O6 | 0.0607 (13) | 0.0268 (9) | 0.0744 (14) | −0.0121 (8) | −0.0153 (11) | −0.0160 (8) |
N1 | 0.0493 (15) | 0.0321 (11) | 0.0514 (15) | −0.0160 (9) | −0.0103 (12) | −0.0145 (10) |
N2 | 0.0591 (19) | 0.0600 (17) | 0.073 (2) | −0.0272 (13) | 0.0102 (15) | −0.0244 (15) |
N3 | 0.0582 (15) | 0.0299 (11) | 0.0519 (15) | −0.0129 (9) | −0.0020 (12) | −0.0162 (10) |
N4 | 0.0600 (16) | 0.0439 (12) | 0.0524 (15) | −0.0193 (10) | −0.0031 (13) | −0.0198 (11) |
N5 | 0.0594 (15) | 0.0348 (11) | 0.0578 (17) | −0.0151 (10) | −0.0033 (13) | −0.0204 (10) |
C1 | 0.0413 (15) | 0.0333 (13) | 0.0403 (16) | −0.0136 (11) | −0.0012 (13) | −0.0146 (11) |
C2 | 0.0385 (15) | 0.0332 (12) | 0.0394 (16) | −0.0127 (10) | −0.0031 (12) | −0.0127 (11) |
C3 | 0.0456 (15) | 0.0325 (12) | 0.0424 (16) | −0.0143 (10) | −0.0040 (13) | −0.0175 (11) |
C4 | 0.0413 (15) | 0.0325 (12) | 0.0372 (16) | −0.0121 (10) | −0.0002 (12) | −0.0135 (11) |
C5 | 0.0409 (15) | 0.0351 (13) | 0.0353 (15) | −0.0089 (11) | −0.0027 (12) | −0.0123 (11) |
C6 | 0.0540 (18) | 0.0454 (15) | 0.0519 (19) | −0.0155 (12) | −0.0107 (15) | −0.0148 (13) |
C7 | 0.0608 (19) | 0.0373 (14) | 0.061 (2) | −0.0176 (12) | −0.0169 (16) | −0.0112 (13) |
C8 | 0.0593 (19) | 0.0412 (15) | 0.0460 (17) | −0.0169 (13) | −0.0050 (15) | −0.0153 (12) |
C9 | 0.099 (3) | 0.080 (2) | 0.087 (3) | −0.029 (2) | −0.052 (3) | −0.0073 (19) |
C10 | 0.0405 (15) | 0.0309 (12) | 0.0403 (16) | −0.0134 (10) | −0.0036 (13) | −0.0116 (11) |
C11 | 0.0507 (17) | 0.0458 (14) | 0.0583 (19) | −0.0268 (12) | 0.0067 (15) | −0.0257 (13) |
C12 | 0.0542 (18) | 0.0480 (15) | 0.0581 (19) | −0.0233 (13) | 0.0090 (15) | −0.0293 (13) |
C13 | 0.0443 (16) | 0.0421 (14) | 0.0538 (19) | −0.0181 (11) | 0.0012 (15) | −0.0160 (13) |
C14 | 0.065 (2) | 0.074 (2) | 0.076 (2) | −0.0469 (16) | 0.0104 (19) | −0.0384 (18) |
C15 | 0.058 (2) | 0.0669 (18) | 0.071 (2) | −0.0336 (14) | 0.0049 (17) | −0.0419 (16) |
C16 | 0.0511 (17) | 0.0351 (13) | 0.0378 (16) | −0.0163 (12) | 0.0029 (14) | −0.0148 (11) |
C17 | 0.0524 (17) | 0.0429 (14) | 0.0441 (18) | −0.0194 (12) | 0.0002 (14) | −0.0175 (13) |
C18 | 0.094 (3) | 0.066 (2) | 0.066 (2) | −0.0363 (18) | 0.007 (2) | −0.0339 (18) |
C19 | 0.119 (4) | 0.106 (3) | 0.049 (2) | −0.062 (2) | 0.006 (2) | −0.027 (2) |
C20 | 0.108 (3) | 0.070 (2) | 0.063 (3) | −0.045 (2) | −0.019 (2) | −0.0019 (18) |
C21 | 0.077 (2) | 0.0436 (16) | 0.069 (2) | −0.0221 (14) | −0.0193 (19) | −0.0097 (15) |
C22 | 0.0478 (17) | 0.0359 (13) | 0.0557 (19) | −0.0157 (11) | −0.0072 (15) | −0.0163 (12) |
Geometric parameters (Å, º) top
O1—C8 | 1.329 (3) | C6—H6B | 0.9600 |
O1—C9 | 1.454 (4) | C6—H6C | 0.9600 |
O2—C8 | 1.195 (4) | C7—H7A | 0.9600 |
O3—N2 | 1.217 (8) | C7—H7B | 0.9600 |
O4—N2 | 1.254 (7) | C7—H7C | 0.9600 |
O3'—N2 | 1.223 (6) | C9—H9A | 0.9600 |
O4'—N2 | 1.244 (5) | C9—H9B | 0.9600 |
O5—C16 | 1.193 (3) | C9—H9C | 0.9600 |
O6—N3 | 1.372 (2) | C10—C15 | 1.380 (4) |
O6—C16 | 1.435 (3) | C10—C11 | 1.386 (3) |
N1—C5 | 1.377 (3) | C11—C12 | 1.372 (4) |
N1—C1 | 1.380 (3) | C11—H11 | 0.9300 |
N1—H1 | 0.86 (3) | C12—C13 | 1.375 (4) |
N2—C13 | 1.466 (4) | C12—H12 | 0.9300 |
N3—N4 | 1.336 (3) | C13—C14 | 1.364 (4) |
N3—C17 | 1.356 (3) | C14—C15 | 1.385 (4) |
N4—N5 | 1.314 (3) | C14—H14 | 0.9300 |
N5—C22 | 1.369 (4) | C15—H15 | 0.9300 |
C1—C2 | 1.345 (4) | C17—C22 | 1.377 (3) |
C1—C7 | 1.506 (3) | C17—C18 | 1.380 (4) |
C2—C8 | 1.466 (4) | C18—C19 | 1.373 (5) |
C2—C3 | 1.527 (3) | C18—H18 | 0.9300 |
C3—C4 | 1.520 (3) | C19—C20 | 1.380 (5) |
C3—C10 | 1.520 (4) | C19—H19 | 0.9300 |
C3—H3 | 0.9800 | C20—C21 | 1.339 (5) |
C4—C5 | 1.368 (4) | C20—H20 | 0.9300 |
C4—C16 | 1.443 (3) | C21—C22 | 1.397 (4) |
C5—C6 | 1.494 (4) | C21—H21 | 0.9300 |
C6—H6A | 0.9600 | | |
| | | |
C8—O1—C9 | 115.3 (2) | H7B—C7—H7C | 109.5 |
N3—O6—C16 | 112.87 (18) | O2—C8—O1 | 120.0 (3) |
C5—N1—C1 | 123.5 (2) | O2—C8—C2 | 123.4 (3) |
C5—N1—H1 | 113.2 (18) | O1—C8—C2 | 116.6 (3) |
C1—N1—H1 | 121.5 (18) | O1—C9—H9A | 109.5 |
O3—N2—O3' | 19.2 (13) | O1—C9—H9B | 109.5 |
O3—N2—O4' | 116.1 (11) | H9A—C9—H9B | 109.5 |
O3'—N2—O4' | 122.8 (6) | O1—C9—H9C | 109.5 |
O3—N2—O4 | 122.6 (9) | H9A—C9—H9C | 109.5 |
O3'—N2—O4 | 115.2 (8) | H9B—C9—H9C | 109.5 |
O4'—N2—O4 | 37.8 (8) | C15—C10—C11 | 117.9 (3) |
O3—N2—C13 | 120.4 (10) | C15—C10—C3 | 120.6 (2) |
O3'—N2—C13 | 119.0 (5) | C11—C10—C3 | 121.5 (2) |
O4'—N2—C13 | 118.0 (4) | C12—C11—C10 | 122.0 (3) |
O4—N2—C13 | 115.0 (5) | C12—C11—H11 | 119.0 |
N4—N3—C17 | 113.25 (19) | C10—C11—H11 | 119.0 |
N4—N3—O6 | 118.6 (2) | C11—C12—C13 | 118.2 (3) |
C17—N3—O6 | 127.6 (2) | C11—C12—H12 | 120.9 |
N5—N4—N3 | 106.5 (2) | C13—C12—H12 | 120.9 |
N4—N5—C22 | 108.5 (2) | C14—C13—C12 | 121.9 (3) |
C2—C1—N1 | 119.0 (2) | C14—C13—N2 | 119.3 (3) |
C2—C1—C7 | 128.3 (2) | C12—C13—N2 | 118.7 (3) |
N1—C1—C7 | 112.7 (2) | C13—C14—C15 | 118.8 (3) |
C1—C2—C8 | 126.2 (2) | C13—C14—H14 | 120.6 |
C1—C2—C3 | 120.9 (2) | C15—C14—H14 | 120.6 |
C8—C2—C3 | 113.0 (2) | C10—C15—C14 | 121.2 (3) |
C4—C3—C10 | 111.5 (2) | C10—C15—H15 | 119.4 |
C4—C3—C2 | 110.2 (2) | C14—C15—H15 | 119.4 |
C10—C3—C2 | 111.49 (18) | O5—C16—O6 | 119.7 (2) |
C4—C3—H3 | 107.8 | O5—C16—C4 | 132.4 (3) |
C10—C3—H3 | 107.8 | O6—C16—C4 | 107.9 (2) |
C2—C3—H3 | 107.8 | N3—C17—C22 | 102.2 (2) |
C5—C4—C16 | 119.6 (2) | N3—C17—C18 | 134.4 (2) |
C5—C4—C3 | 120.4 (2) | C22—C17—C18 | 123.4 (3) |
C16—C4—C3 | 119.9 (2) | C19—C18—C17 | 114.7 (3) |
C4—C5—N1 | 118.6 (2) | C19—C18—H18 | 122.7 |
C4—C5—C6 | 126.7 (2) | C17—C18—H18 | 122.7 |
N1—C5—C6 | 114.7 (2) | C18—C19—C20 | 122.2 (3) |
C5—C6—H6A | 109.5 | C18—C19—H19 | 118.9 |
C5—C6—H6B | 109.5 | C20—C19—H19 | 118.9 |
H6A—C6—H6B | 109.5 | C21—C20—C19 | 123.1 (3) |
C5—C6—H6C | 109.5 | C21—C20—H20 | 118.5 |
H6A—C6—H6C | 109.5 | C19—C20—H20 | 118.5 |
H6B—C6—H6C | 109.5 | C20—C21—C22 | 116.3 (3) |
C1—C7—H7A | 109.5 | C20—C21—H21 | 121.8 |
C1—C7—H7B | 109.5 | C22—C21—H21 | 121.8 |
H7A—C7—H7B | 109.5 | N5—C22—C17 | 109.6 (2) |
C1—C7—H7C | 109.5 | N5—C22—C21 | 130.0 (2) |
H7A—C7—H7C | 109.5 | C17—C22—C21 | 120.3 (3) |
| | | |
C16—O6—N3—N4 | −111.1 (3) | C11—C12—C13—C14 | −0.1 (4) |
C16—O6—N3—C17 | 77.8 (3) | C11—C12—C13—N2 | 178.7 (2) |
C17—N3—N4—N5 | −1.0 (3) | O3—N2—C13—C14 | −164.9 (13) |
O6—N3—N4—N5 | −173.3 (2) | O3'—N2—C13—C14 | 173.0 (8) |
N3—N4—N5—C22 | 0.2 (3) | O4'—N2—C13—C14 | −12.0 (8) |
C5—N1—C1—C2 | 16.1 (4) | O4—N2—C13—C14 | 30.3 (15) |
C5—N1—C1—C7 | −163.3 (2) | O3—N2—C13—C12 | 16.2 (14) |
N1—C1—C2—C8 | −173.3 (2) | O3'—N2—C13—C12 | −5.9 (8) |
C7—C1—C2—C8 | 6.0 (5) | O4'—N2—C13—C12 | 169.1 (7) |
N1—C1—C2—C3 | 6.4 (4) | O4—N2—C13—C12 | −148.6 (15) |
C7—C1—C2—C3 | −174.4 (2) | C12—C13—C14—C15 | −0.6 (4) |
C1—C2—C3—C4 | −25.4 (3) | N2—C13—C14—C15 | −179.5 (3) |
C8—C2—C3—C4 | 154.3 (2) | C11—C10—C15—C14 | −0.7 (4) |
C1—C2—C3—C10 | 99.0 (3) | C3—C10—C15—C14 | 177.9 (2) |
C8—C2—C3—C10 | −81.3 (3) | C13—C14—C15—C10 | 1.0 (5) |
C10—C3—C4—C5 | −98.5 (3) | N3—O6—C16—O5 | 1.7 (3) |
C2—C3—C4—C5 | 25.9 (3) | N3—O6—C16—C4 | −178.6 (2) |
C10—C3—C4—C16 | 77.9 (3) | C5—C4—C16—O5 | −5.1 (4) |
C2—C3—C4—C16 | −157.8 (2) | C3—C4—C16—O5 | 178.5 (3) |
C16—C4—C5—N1 | 176.1 (2) | C5—C4—C16—O6 | 175.3 (2) |
C3—C4—C5—N1 | −7.6 (4) | C3—C4—C16—O6 | −1.1 (3) |
C16—C4—C5—C6 | −4.1 (4) | N4—N3—C17—C22 | 1.3 (3) |
C3—C4—C5—C6 | 172.3 (2) | O6—N3—C17—C22 | 172.8 (2) |
C1—N1—C5—C4 | −15.4 (4) | N4—N3—C17—C18 | −178.8 (3) |
C1—N1—C5—C6 | 164.7 (2) | O6—N3—C17—C18 | −7.4 (6) |
C9—O1—C8—O2 | −2.5 (5) | N3—C17—C18—C19 | −179.8 (3) |
C9—O1—C8—C2 | 177.1 (3) | C22—C17—C18—C19 | 0.1 (5) |
C1—C2—C8—O2 | −177.9 (3) | C17—C18—C19—C20 | −0.6 (6) |
C3—C2—C8—O2 | 2.4 (4) | C18—C19—C20—C21 | 0.8 (6) |
C1—C2—C8—O1 | 2.5 (4) | C19—C20—C21—C22 | −0.4 (6) |
C3—C2—C8—O1 | −177.2 (2) | N4—N5—C22—C17 | 0.6 (3) |
C4—C3—C10—C15 | −112.1 (3) | N4—N5—C22—C21 | 179.1 (3) |
C2—C3—C10—C15 | 124.2 (3) | N3—C17—C22—N5 | −1.1 (3) |
C4—C3—C10—C11 | 66.4 (3) | C18—C17—C22—N5 | 179.0 (3) |
C2—C3—C10—C11 | −57.2 (3) | N3—C17—C22—C21 | −179.8 (3) |
C15—C10—C11—C12 | −0.1 (4) | C18—C17—C22—C21 | 0.3 (5) |
C3—C10—C11—C12 | −178.7 (2) | C20—C21—C22—N5 | −178.6 (3) |
C10—C11—C12—C13 | 0.5 (4) | C20—C21—C22—C17 | −0.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N5i | 0.86 (3) | 2.35 (3) | 3.156 (3) | 155 (2) |
C15—H15···O2ii | 0.93 | 2.45 | 3.184 (4) | 136 |
C18—H18···O3′iii | 0.93 | 2.42 | 3.333 (8) | 167 |
C21—H21···O4′iv | 0.93 | 2.60 | 3.230 (9) | 126 |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x, −y+1, −z+1; (iv) −x, −y, −z+1. |