The title compound, C
26H
28N
2O
6, is a nefidipine analogue. The dihydropyridine ring shows a flattened-boat conformation. The crystal packing is stabilized by intermolecular N—H
O hydrogen bonds.
Supporting information
CCDC reference: 627305
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.076
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.35 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.37 Ratio
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.85
From the CIF: _reflns_number_total 3086
Count of symmetry unique reflns 3091
Completeness (_total/calc) 99.84%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
PLAT792_ALERT_1_G Check the Absolute Configuration of C3 = ... S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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: CrystalStructure (Rigaku, 2005); software used to prepare material for publication: CrystalStructure.
3-Benzyl 5-
tert-butyl
2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
top
Crystal data top
C26H28N2O6 | Dx = 1.249 Mg m−3 |
Mr = 464.50 | Melting point = 401–402 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2c -2ac | Cell parameters from 6098 reflections |
a = 24.359 (2) Å | θ = 1.7–27.9° |
b = 9.2553 (8) Å | µ = 0.09 mm−1 |
c = 10.9579 (12) Å | T = 113 K |
V = 2470.4 (4) Å3 | Block, yellow |
Z = 4 | 0.36 × 0.34 × 0.24 mm |
F(000) = 984 | |
Data collection top
Rigaku Saturn diffractometer | 3086 independent reflections |
Radiation source: rotating anode | 2762 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.045 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.9°, θmin = 1.7° |
ω scans | h = −32→32 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −12→8 |
Tmin = 0.96, Tmax = 0.98 | l = −8→14 |
14798 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0461P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.076 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.22 e Å−3 |
3086 reflections | Δρmin = −0.17 e Å−3 |
318 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0253 (16) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Data have been merged |
Secondary atom site location: difference Fourier map | |
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 | |
O1 | 0.21240 (5) | 0.25553 (14) | 0.48790 (15) | 0.0268 (3) | |
O2 | 0.23889 (4) | 0.41710 (12) | 0.34428 (13) | 0.0192 (3) | |
O3 | 0.03328 (5) | 0.65771 (15) | 0.09103 (14) | 0.0282 (3) | |
O4 | 0.12027 (5) | 0.72813 (13) | 0.12369 (13) | 0.0204 (3) | |
O5 | 0.15574 (7) | 0.93348 (16) | 0.74968 (15) | 0.0410 (4) | |
O6 | 0.09064 (6) | 0.78209 (16) | 0.70860 (15) | 0.0317 (4) | |
N1 | 0.04936 (6) | 0.40772 (17) | 0.41520 (16) | 0.0199 (3) | |
N3 | 0.13286 (6) | 0.84789 (17) | 0.68126 (16) | 0.0251 (4) | |
C1 | 0.10076 (6) | 0.34918 (18) | 0.44166 (18) | 0.0176 (4) | |
C2 | 0.14583 (6) | 0.40706 (18) | 0.38777 (18) | 0.0167 (4) | |
C3 | 0.14194 (6) | 0.54300 (18) | 0.30915 (17) | 0.0159 (4) | |
H3 | 0.1667 | 0.5304 | 0.2371 | 0.019* | |
C4 | 0.08328 (6) | 0.56349 (18) | 0.26206 (18) | 0.0168 (4) | |
C5 | 0.04007 (6) | 0.50318 (18) | 0.32148 (18) | 0.0184 (4) | |
C6 | 0.09828 (7) | 0.2221 (2) | 0.5258 (2) | 0.0246 (4) | |
H6A | 0.0604 | 0.2080 | 0.5536 | 0.029* | |
H6B | 0.1220 | 0.2395 | 0.5965 | 0.029* | |
H6C | 0.1108 | 0.1354 | 0.4826 | 0.029* | |
C7 | −0.01996 (6) | 0.5269 (2) | 0.2957 (2) | 0.0240 (4) | |
H7A | −0.0412 | 0.5103 | 0.3703 | 0.029* | |
H7B | −0.0321 | 0.4595 | 0.2322 | 0.029* | |
H7C | −0.0257 | 0.6264 | 0.2677 | 0.029* | |
C8 | 0.20123 (6) | 0.34884 (18) | 0.41419 (18) | 0.0169 (4) | |
C9 | 0.29863 (6) | 0.39426 (19) | 0.36270 (19) | 0.0205 (4) | |
C10 | 0.32286 (7) | 0.4932 (2) | 0.2666 (2) | 0.0295 (5) | |
H10A | 0.3113 | 0.5929 | 0.2826 | 0.035* | |
H10B | 0.3099 | 0.4635 | 0.1858 | 0.035* | |
H10C | 0.3630 | 0.4872 | 0.2694 | 0.035* | |
C11 | 0.31418 (8) | 0.4427 (2) | 0.4906 (2) | 0.0307 (5) | |
H11A | 0.3014 | 0.5419 | 0.5037 | 0.037* | |
H11B | 0.3542 | 0.4388 | 0.4999 | 0.037* | |
H11C | 0.2970 | 0.3785 | 0.5505 | 0.037* | |
C12 | 0.31399 (7) | 0.2382 (2) | 0.3378 (2) | 0.0283 (5) | |
H12A | 0.2989 | 0.1764 | 0.4022 | 0.034* | |
H12B | 0.3541 | 0.2288 | 0.3362 | 0.034* | |
H12C | 0.2989 | 0.2086 | 0.2587 | 0.034* | |
C13 | 0.07496 (7) | 0.65146 (19) | 0.15319 (18) | 0.0184 (4) | |
C14 | 0.11696 (7) | 0.8142 (2) | 0.0122 (2) | 0.0235 (4) | |
H14A | 0.0988 | 0.7565 | −0.0523 | 0.028* | |
H14B | 0.1546 | 0.8372 | −0.0160 | 0.028* | |
C15 | 0.08555 (7) | 0.9531 (2) | 0.0305 (2) | 0.0237 (4) | |
C16 | 0.10043 (10) | 1.0483 (2) | 0.1228 (2) | 0.0403 (6) | |
H16 | 0.1297 | 1.0244 | 0.1763 | 0.048* | |
C17 | 0.07263 (13) | 1.1780 (3) | 0.1370 (3) | 0.0533 (7) | |
H17 | 0.0829 | 1.2424 | 0.2005 | 0.064* | |
C18 | 0.03018 (11) | 1.2141 (3) | 0.0596 (3) | 0.0488 (7) | |
H18 | 0.0116 | 1.3036 | 0.0692 | 0.059* | |
C19 | 0.01474 (9) | 1.1201 (3) | −0.0317 (3) | 0.0415 (6) | |
H19 | −0.0148 | 1.1444 | −0.0845 | 0.050* | |
C20 | 0.04250 (8) | 0.9893 (2) | −0.0467 (2) | 0.0295 (5) | |
H20 | 0.0319 | 0.9248 | −0.1099 | 0.035* | |
C21 | 0.16163 (6) | 0.67421 (18) | 0.38105 (18) | 0.0171 (4) | |
C22 | 0.13831 (6) | 0.70441 (19) | 0.49354 (19) | 0.0180 (4) | |
H22 | 0.1095 | 0.6457 | 0.5243 | 0.022* | |
C23 | 0.15745 (7) | 0.82129 (19) | 0.56099 (19) | 0.0204 (4) | |
C24 | 0.19894 (7) | 0.9118 (2) | 0.5196 (2) | 0.0240 (4) | |
H24 | 0.2115 | 0.9909 | 0.5674 | 0.029* | |
C25 | 0.22136 (7) | 0.8827 (2) | 0.4062 (2) | 0.0264 (5) | |
H25 | 0.2495 | 0.9433 | 0.3748 | 0.032* | |
C26 | 0.20317 (7) | 0.76555 (18) | 0.3375 (2) | 0.0217 (4) | |
H26 | 0.2191 | 0.7472 | 0.2600 | 0.026* | |
H1 | 0.0226 (9) | 0.377 (2) | 0.457 (2) | 0.033 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0209 (6) | 0.0265 (7) | 0.0331 (9) | 0.0012 (5) | 0.0001 (6) | 0.0101 (7) |
O2 | 0.0114 (5) | 0.0230 (6) | 0.0233 (8) | 0.0002 (4) | 0.0007 (5) | 0.0030 (6) |
O3 | 0.0236 (6) | 0.0357 (8) | 0.0254 (9) | −0.0031 (5) | −0.0107 (6) | 0.0038 (7) |
O4 | 0.0183 (5) | 0.0251 (7) | 0.0178 (8) | 0.0001 (5) | 0.0004 (5) | 0.0041 (6) |
O5 | 0.0616 (10) | 0.0338 (9) | 0.0275 (9) | −0.0164 (7) | −0.0011 (8) | −0.0121 (8) |
O6 | 0.0337 (7) | 0.0348 (8) | 0.0266 (9) | −0.0049 (6) | 0.0043 (6) | −0.0067 (7) |
N1 | 0.0131 (6) | 0.0257 (8) | 0.0210 (9) | −0.0013 (5) | 0.0033 (6) | 0.0039 (7) |
N3 | 0.0358 (9) | 0.0186 (8) | 0.0208 (10) | 0.0001 (7) | −0.0038 (7) | −0.0019 (8) |
C1 | 0.0160 (7) | 0.0182 (8) | 0.0186 (11) | −0.0009 (6) | 0.0000 (7) | −0.0035 (8) |
C2 | 0.0165 (7) | 0.0157 (8) | 0.0179 (10) | 0.0007 (6) | 0.0001 (7) | −0.0030 (8) |
C3 | 0.0130 (7) | 0.0180 (8) | 0.0166 (10) | −0.0002 (6) | 0.0010 (7) | −0.0001 (8) |
C4 | 0.0154 (7) | 0.0176 (9) | 0.0174 (10) | 0.0001 (6) | −0.0016 (7) | −0.0047 (8) |
C5 | 0.0150 (7) | 0.0201 (9) | 0.0201 (11) | 0.0000 (6) | −0.0008 (7) | −0.0042 (8) |
C6 | 0.0188 (8) | 0.0253 (10) | 0.0296 (13) | −0.0028 (7) | 0.0028 (8) | 0.0044 (9) |
C7 | 0.0143 (8) | 0.0298 (10) | 0.0278 (12) | −0.0005 (7) | −0.0009 (7) | −0.0004 (9) |
C8 | 0.0160 (7) | 0.0158 (8) | 0.0188 (11) | −0.0011 (6) | 0.0002 (7) | −0.0016 (8) |
C9 | 0.0114 (7) | 0.0224 (9) | 0.0278 (12) | −0.0002 (6) | −0.0021 (7) | −0.0005 (9) |
C10 | 0.0166 (8) | 0.0333 (11) | 0.0385 (14) | −0.0011 (7) | 0.0037 (8) | 0.0090 (10) |
C11 | 0.0225 (8) | 0.0376 (12) | 0.0320 (13) | −0.0047 (8) | −0.0054 (9) | −0.0065 (11) |
C12 | 0.0198 (8) | 0.0261 (10) | 0.0392 (13) | 0.0028 (7) | 0.0039 (9) | −0.0029 (10) |
C13 | 0.0169 (7) | 0.0191 (9) | 0.0191 (11) | 0.0007 (6) | −0.0016 (7) | −0.0043 (8) |
C14 | 0.0269 (8) | 0.0264 (10) | 0.0173 (11) | 0.0027 (8) | 0.0026 (8) | 0.0044 (9) |
C15 | 0.0277 (8) | 0.0222 (10) | 0.0211 (11) | 0.0005 (7) | 0.0039 (8) | 0.0016 (9) |
C16 | 0.0557 (14) | 0.0345 (12) | 0.0306 (15) | 0.0037 (10) | −0.0077 (12) | −0.0025 (11) |
C17 | 0.088 (2) | 0.0318 (13) | 0.0397 (17) | 0.0072 (13) | 0.0028 (16) | −0.0127 (13) |
C18 | 0.0688 (16) | 0.0294 (12) | 0.0482 (18) | 0.0153 (11) | 0.0223 (14) | 0.0014 (13) |
C19 | 0.0371 (11) | 0.0395 (13) | 0.0480 (17) | 0.0150 (10) | 0.0058 (11) | 0.0107 (13) |
C20 | 0.0303 (9) | 0.0298 (11) | 0.0283 (13) | 0.0030 (8) | 0.0013 (9) | 0.0007 (10) |
C21 | 0.0141 (7) | 0.0169 (8) | 0.0203 (11) | 0.0011 (6) | −0.0040 (7) | 0.0024 (8) |
C22 | 0.0163 (7) | 0.0175 (8) | 0.0201 (11) | −0.0003 (6) | −0.0022 (7) | 0.0004 (8) |
C23 | 0.0236 (8) | 0.0181 (9) | 0.0196 (11) | 0.0020 (7) | −0.0046 (7) | −0.0003 (8) |
C24 | 0.0255 (8) | 0.0168 (9) | 0.0299 (13) | −0.0028 (7) | −0.0069 (8) | −0.0017 (9) |
C25 | 0.0228 (8) | 0.0205 (9) | 0.0360 (14) | −0.0062 (7) | 0.0007 (9) | 0.0025 (9) |
C26 | 0.0182 (7) | 0.0225 (9) | 0.0243 (11) | −0.0008 (6) | 0.0006 (7) | 0.0018 (9) |
Geometric parameters (Å, º) top
O1—C8 | 1.213 (2) | C10—H10B | 0.9800 |
O2—C8 | 1.352 (2) | C10—H10C | 0.9800 |
O2—C9 | 1.4842 (18) | C11—H11A | 0.9800 |
O3—C13 | 1.224 (2) | C11—H11B | 0.9800 |
O4—C13 | 1.351 (2) | C11—H11C | 0.9800 |
O4—C14 | 1.461 (3) | C12—H12A | 0.9800 |
O5—N3 | 1.225 (2) | C12—H12B | 0.9800 |
O6—N3 | 1.232 (2) | C12—H12C | 0.9800 |
N1—C5 | 1.374 (3) | C14—C15 | 1.510 (3) |
N1—C1 | 1.395 (2) | C14—H14A | 0.9900 |
N1—H1 | 0.84 (2) | C14—H14B | 0.9900 |
N3—C23 | 1.468 (3) | C15—C20 | 1.388 (3) |
C1—C2 | 1.357 (2) | C15—C16 | 1.389 (3) |
C1—C6 | 1.496 (3) | C16—C17 | 1.387 (3) |
C2—C8 | 1.482 (2) | C16—H16 | 0.9500 |
C2—C3 | 1.528 (2) | C17—C18 | 1.378 (4) |
C3—C21 | 1.525 (2) | C17—H17 | 0.9500 |
C3—C4 | 1.531 (2) | C18—C19 | 1.378 (4) |
C3—H3 | 1.0000 | C18—H18 | 0.9500 |
C4—C5 | 1.358 (2) | C19—C20 | 1.397 (3) |
C4—C13 | 1.458 (3) | C19—H19 | 0.9500 |
C5—C7 | 1.506 (2) | C20—H20 | 0.9500 |
C6—H6A | 0.9800 | C21—C22 | 1.386 (3) |
C6—H6B | 0.9800 | C21—C26 | 1.402 (2) |
C6—H6C | 0.9800 | C22—C23 | 1.391 (2) |
C7—H7A | 0.9800 | C22—H22 | 0.9500 |
C7—H7B | 0.9800 | C23—C24 | 1.389 (3) |
C7—H7C | 0.9800 | C24—C25 | 1.385 (3) |
C9—C10 | 1.515 (3) | C24—H24 | 0.9500 |
C9—C12 | 1.517 (3) | C25—C26 | 1.392 (3) |
C9—C11 | 1.519 (3) | C25—H25 | 0.9500 |
C10—H10A | 0.9800 | C26—H26 | 0.9500 |
| | | |
C8—O2—C9 | 121.44 (14) | H11A—C11—H11B | 109.5 |
C13—O4—C14 | 116.20 (14) | C9—C11—H11C | 109.5 |
C5—N1—C1 | 123.58 (15) | H11A—C11—H11C | 109.5 |
C5—N1—H1 | 119.4 (16) | H11B—C11—H11C | 109.5 |
C1—N1—H1 | 116.9 (16) | C9—C12—H12A | 109.5 |
O5—N3—O6 | 123.41 (18) | C9—C12—H12B | 109.5 |
O5—N3—C23 | 118.18 (16) | H12A—C12—H12B | 109.5 |
O6—N3—C23 | 118.41 (16) | C9—C12—H12C | 109.5 |
C2—C1—N1 | 118.85 (17) | H12A—C12—H12C | 109.5 |
C2—C1—C6 | 127.69 (15) | H12B—C12—H12C | 109.5 |
N1—C1—C6 | 113.41 (14) | O3—C13—O4 | 121.30 (18) |
C1—C2—C8 | 120.55 (16) | O3—C13—C4 | 126.64 (16) |
C1—C2—C3 | 121.36 (14) | O4—C13—C4 | 112.05 (14) |
C8—C2—C3 | 117.79 (13) | O4—C14—C15 | 112.43 (16) |
C21—C3—C2 | 110.18 (15) | O4—C14—H14A | 109.1 |
C21—C3—C4 | 111.65 (13) | C15—C14—H14A | 109.1 |
C2—C3—C4 | 110.48 (13) | O4—C14—H14B | 109.1 |
C21—C3—H3 | 108.1 | C15—C14—H14B | 109.1 |
C2—C3—H3 | 108.1 | H14A—C14—H14B | 107.9 |
C4—C3—H3 | 108.1 | C20—C15—C16 | 119.21 (18) |
C5—C4—C13 | 120.93 (15) | C20—C15—C14 | 120.49 (19) |
C5—C4—C3 | 120.73 (17) | C16—C15—C14 | 120.28 (19) |
C13—C4—C3 | 118.33 (14) | C17—C16—C15 | 120.2 (2) |
C4—C5—N1 | 119.69 (15) | C17—C16—H16 | 119.9 |
C4—C5—C7 | 127.08 (18) | C15—C16—H16 | 119.9 |
N1—C5—C7 | 113.22 (15) | C18—C17—C16 | 120.4 (3) |
C1—C6—H6A | 109.5 | C18—C17—H17 | 119.8 |
C1—C6—H6B | 109.5 | C16—C17—H17 | 119.8 |
H6A—C6—H6B | 109.5 | C19—C18—C17 | 119.9 (2) |
C1—C6—H6C | 109.5 | C19—C18—H18 | 120.0 |
H6A—C6—H6C | 109.5 | C17—C18—H18 | 120.0 |
H6B—C6—H6C | 109.5 | C18—C19—C20 | 120.0 (2) |
C5—C7—H7A | 109.5 | C18—C19—H19 | 120.0 |
C5—C7—H7B | 109.5 | C20—C19—H19 | 120.0 |
H7A—C7—H7B | 109.5 | C15—C20—C19 | 120.2 (2) |
C5—C7—H7C | 109.5 | C15—C20—H20 | 119.9 |
H7A—C7—H7C | 109.5 | C19—C20—H20 | 119.9 |
H7B—C7—H7C | 109.5 | C22—C21—C26 | 118.48 (17) |
O1—C8—O2 | 123.89 (14) | C22—C21—C3 | 119.43 (15) |
O1—C8—C2 | 126.39 (16) | C26—C21—C3 | 122.09 (17) |
O2—C8—C2 | 109.71 (15) | C21—C22—C23 | 119.49 (16) |
O2—C9—C10 | 101.62 (14) | C21—C22—H22 | 120.3 |
O2—C9—C12 | 110.67 (14) | C23—C22—H22 | 120.3 |
C10—C9—C12 | 110.76 (17) | C24—C23—C22 | 122.68 (19) |
O2—C9—C11 | 109.15 (15) | C24—C23—N3 | 119.24 (17) |
C10—C9—C11 | 111.44 (16) | C22—C23—N3 | 118.09 (16) |
C12—C9—C11 | 112.67 (17) | C25—C24—C23 | 117.54 (18) |
C9—C10—H10A | 109.5 | C25—C24—H24 | 121.2 |
C9—C10—H10B | 109.5 | C23—C24—H24 | 121.2 |
H10A—C10—H10B | 109.5 | C24—C25—C26 | 120.77 (17) |
C9—C10—H10C | 109.5 | C24—C25—H25 | 119.6 |
H10A—C10—H10C | 109.5 | C26—C25—H25 | 119.6 |
H10B—C10—H10C | 109.5 | C25—C26—C21 | 121.03 (19) |
C9—C11—H11A | 109.5 | C25—C26—H26 | 119.5 |
C9—C11—H11B | 109.5 | C21—C26—H26 | 119.5 |
| | | |
C5—N1—C1—C2 | 12.3 (3) | C3—C4—C13—O3 | 165.70 (18) |
C5—N1—C1—C6 | −165.56 (17) | C5—C4—C13—O4 | 165.81 (16) |
N1—C1—C2—C8 | 179.49 (16) | C3—C4—C13—O4 | −13.1 (2) |
C6—C1—C2—C8 | −3.0 (3) | C13—O4—C14—C15 | 78.4 (2) |
N1—C1—C2—C3 | 6.0 (3) | O4—C14—C15—C20 | −127.87 (19) |
C6—C1—C2—C3 | −176.56 (18) | O4—C14—C15—C16 | 53.9 (2) |
C1—C2—C3—C21 | 101.84 (19) | C20—C15—C16—C17 | −0.2 (3) |
C8—C2—C3—C21 | −71.85 (19) | C14—C15—C16—C17 | 178.0 (2) |
C1—C2—C3—C4 | −22.0 (2) | C15—C16—C17—C18 | −0.3 (4) |
C8—C2—C3—C4 | 164.30 (16) | C16—C17—C18—C19 | 0.7 (4) |
C21—C3—C4—C5 | −99.72 (19) | C17—C18—C19—C20 | −0.7 (4) |
C2—C3—C4—C5 | 23.3 (2) | C16—C15—C20—C19 | 0.3 (3) |
C21—C3—C4—C13 | 79.2 (2) | C14—C15—C20—C19 | −177.94 (19) |
C2—C3—C4—C13 | −157.81 (15) | C18—C19—C20—C15 | 0.2 (3) |
C13—C4—C5—N1 | 172.62 (16) | C2—C3—C21—C22 | −54.09 (18) |
C3—C4—C5—N1 | −8.5 (3) | C4—C3—C21—C22 | 69.1 (2) |
C13—C4—C5—C7 | −6.4 (3) | C2—C3—C21—C26 | 125.38 (17) |
C3—C4—C5—C7 | 172.45 (17) | C4—C3—C21—C26 | −111.45 (18) |
C1—N1—C5—C4 | −10.9 (3) | C26—C21—C22—C23 | −1.6 (2) |
C1—N1—C5—C7 | 168.25 (17) | C3—C21—C22—C23 | 177.93 (15) |
C9—O2—C8—O1 | −7.1 (3) | C21—C22—C23—C24 | 0.9 (3) |
C9—O2—C8—C2 | 172.01 (14) | C21—C22—C23—N3 | −178.36 (15) |
C1—C2—C8—O1 | −4.9 (3) | O5—N3—C23—C24 | −12.0 (3) |
C3—C2—C8—O1 | 168.89 (19) | O6—N3—C23—C24 | 168.65 (17) |
C1—C2—C8—O2 | 176.02 (16) | O5—N3—C23—C22 | 167.30 (17) |
C3—C2—C8—O2 | −10.2 (2) | O6—N3—C23—C22 | −12.0 (2) |
C8—O2—C9—C10 | −179.12 (16) | C22—C23—C24—C25 | 0.3 (3) |
C8—O2—C9—C12 | 63.2 (2) | N3—C23—C24—C25 | 179.56 (16) |
C8—O2—C9—C11 | −61.3 (2) | C23—C24—C25—C26 | −0.8 (3) |
C14—O4—C13—O3 | −1.9 (2) | C24—C25—C26—C21 | 0.2 (3) |
C14—O4—C13—C4 | 177.00 (15) | C22—C21—C26—C25 | 1.0 (3) |
C5—C4—C13—O3 | −15.4 (3) | C3—C21—C26—C25 | −178.44 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.84 (2) | 2.03 (2) | 2.851 (2) | 164 (2) |
Symmetry code: (i) −x, −y+1, z+1/2. |