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The title compound, C
23H
21N
5O
6·0.5C
4H
8O
2, is an important intermediate in the synthesis of nefidipine-type pharmaceuticals. The crystal packing is stabilized by intermolecular N—H
O hydrogen bonds.
Supporting information
CCDC reference: 620967
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.002 Å
- Disorder in solvent or counterion
- R factor = 0.044
- wR factor = 0.120
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C26
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.19 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
4 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); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
3-(Benzotriazol-1-yl)-5-ethyl-2,6-dimethyl-4-(3-nitrophenyl)-
1,4-dihydropyridine-3,5-dicarboxylate ethyl acetate hemisolvate
top
Crystal data top
C23H21N5O6·0.5C4H8O2 | Dx = 1.347 Mg m−3 |
Mr = 507.50 | Melting point = 459–460 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71070 Å |
a = 10.2988 (13) Å | Cell parameters from 7583 reflections |
b = 17.092 (2) Å | θ = 1.9–28.7° |
c = 14.2211 (17) Å | µ = 0.10 mm−1 |
β = 90.162 (4)° | T = 113 K |
V = 2503.2 (5) Å3 | Block, colorless |
Z = 4 | 0.22 × 0.18 × 0.14 mm |
F(000) = 1064 | |
Data collection top
Rigaku Saturn diffractometer | 5438 independent reflections |
Radiation source: rotating anode | 4048 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.046 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.0°, θmin = 1.9° |
ω scans | h = −13→9 |
Absorption correction: multi-scan (Jacobson, 1998) | k = −21→21 |
Tmin = 0.973, Tmax = 0.986 | l = −17→18 |
22057 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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0708P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5438 reflections | Δρmax = 0.29 e Å−3 |
370 parameters | Δρmin = −0.32 e Å−3 |
10 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0196 (16) |
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 | 0.28657 (9) | 0.45502 (6) | 0.43373 (7) | 0.0201 (2) | |
O2 | 0.13178 (11) | 0.52817 (6) | 0.35954 (8) | 0.0301 (3) | |
O3 | 0.04282 (11) | 0.16491 (7) | 0.61631 (8) | 0.0322 (3) | |
O4 | 0.23449 (10) | 0.21671 (6) | 0.57473 (7) | 0.0228 (3) | |
O5 | 0.61363 (11) | 0.30994 (7) | 0.34904 (8) | 0.0327 (3) | |
O6 | 0.62809 (11) | 0.20348 (7) | 0.26665 (9) | 0.0377 (3) | |
N1 | 0.36996 (11) | 0.51563 (7) | 0.41517 (9) | 0.0189 (3) | |
N2 | 0.38520 (12) | 0.57294 (7) | 0.47905 (8) | 0.0211 (3) | |
N3 | 0.47897 (12) | 0.61820 (7) | 0.44871 (9) | 0.0208 (3) | |
N4 | −0.12128 (13) | 0.33610 (8) | 0.42691 (9) | 0.0222 (3) | |
N5 | 0.56480 (12) | 0.25306 (8) | 0.30877 (9) | 0.0233 (3) | |
C1 | 0.45383 (13) | 0.52090 (8) | 0.34167 (10) | 0.0176 (3) | |
C2 | 0.52417 (14) | 0.58817 (8) | 0.36441 (10) | 0.0179 (3) | |
C3 | 0.62195 (15) | 0.61548 (9) | 0.30419 (11) | 0.0220 (3) | |
H3 | 0.6721 | 0.6605 | 0.3190 | 0.026* | |
C4 | 0.64152 (15) | 0.57402 (9) | 0.22281 (11) | 0.0254 (4) | |
H4 | 0.7058 | 0.5913 | 0.1798 | 0.031* | |
C5 | 0.56860 (16) | 0.50635 (9) | 0.20131 (12) | 0.0275 (4) | |
H5A | 0.5855 | 0.4796 | 0.1441 | 0.033* | |
C6 | 0.47428 (15) | 0.47766 (9) | 0.25987 (11) | 0.0243 (4) | |
H6A | 0.4263 | 0.4316 | 0.2457 | 0.029* | |
C7 | 0.15788 (14) | 0.46796 (8) | 0.39854 (10) | 0.0184 (3) | |
C8 | −0.04865 (14) | 0.39962 (9) | 0.40125 (10) | 0.0186 (3) | |
C9 | 0.08145 (14) | 0.39931 (8) | 0.41990 (10) | 0.0169 (3) | |
C10 | 0.14803 (13) | 0.32664 (8) | 0.45939 (10) | 0.0164 (3) | |
H10 | 0.2119 | 0.3441 | 0.5081 | 0.020* | |
C11 | 0.05066 (14) | 0.27271 (8) | 0.50695 (10) | 0.0187 (3) | |
C12 | −0.07737 (14) | 0.27665 (9) | 0.48529 (10) | 0.0202 (3) | |
C13 | −0.12437 (15) | 0.46458 (9) | 0.35544 (11) | 0.0241 (4) | |
H13A | −0.2166 | 0.4506 | 0.3534 | 0.036* | |
H13B | −0.0926 | 0.4727 | 0.2913 | 0.036* | |
H13C | −0.1132 | 0.5129 | 0.3918 | 0.036* | |
C14 | −0.18369 (16) | 0.22246 (10) | 0.51614 (12) | 0.0289 (4) | |
H14A | −0.2051 | 0.1864 | 0.4648 | 0.043* | |
H14B | −0.2608 | 0.2530 | 0.5326 | 0.043* | |
H14C | −0.1546 | 0.1926 | 0.5711 | 0.043* | |
C15 | 0.22301 (14) | 0.28247 (8) | 0.38299 (10) | 0.0162 (3) | |
C16 | 0.35766 (14) | 0.28793 (8) | 0.37917 (10) | 0.0168 (3) | |
H16 | 0.4037 | 0.3199 | 0.4225 | 0.020* | |
C17 | 0.42318 (13) | 0.24594 (8) | 0.31116 (10) | 0.0181 (3) | |
C18 | 0.36254 (15) | 0.19751 (9) | 0.24684 (11) | 0.0242 (4) | |
H18 | 0.4108 | 0.1686 | 0.2019 | 0.029* | |
C19 | 0.22839 (16) | 0.19299 (10) | 0.25078 (11) | 0.0283 (4) | |
H19 | 0.1829 | 0.1609 | 0.2072 | 0.034* | |
C20 | 0.15983 (15) | 0.23490 (9) | 0.31783 (10) | 0.0231 (4) | |
H20 | 0.0678 | 0.2311 | 0.3193 | 0.028* | |
C21 | 0.10319 (15) | 0.21264 (9) | 0.57118 (11) | 0.0212 (3) | |
C22 | 0.29988 (16) | 0.16085 (10) | 0.63541 (12) | 0.0307 (4) | |
H22A | 0.2764 | 0.1068 | 0.6172 | 0.037* | |
H22B | 0.2741 | 0.1692 | 0.7017 | 0.037* | |
C23 | 0.44317 (16) | 0.17342 (10) | 0.62439 (13) | 0.0351 (4) | |
H23A | 0.4678 | 0.1642 | 0.5588 | 0.053* | |
H23B | 0.4904 | 0.1370 | 0.6653 | 0.053* | |
H23C | 0.4650 | 0.2273 | 0.6419 | 0.053* | |
O7 | 0.3476 (3) | 0.9531 (2) | 0.5426 (2) | 0.0735 (10) | 0.50 |
O8 | 0.5451 (5) | 0.9963 (3) | 0.4967 (4) | 0.0479 (15) | 0.50 |
C24 | 0.3546 (7) | 1.0284 (6) | 0.4006 (5) | 0.067 (2) | 0.50 |
H24A | 0.2630 | 1.0178 | 0.3987 | 0.100* | 0.50 |
H24B | 0.3684 | 1.0837 | 0.4070 | 0.100* | 0.50 |
H24C | 0.3939 | 1.0104 | 0.3434 | 0.100* | 0.50 |
C25 | 0.4145 (8) | 0.9875 (6) | 0.4850 (6) | 0.066 (3) | 0.50 |
C26 | 0.5988 (7) | 0.9633 (5) | 0.5803 (5) | 0.0466 (16) | 0.50 |
H26A | 0.5923 | 0.9073 | 0.5785 | 0.056* | 0.50 |
H26B | 0.5527 | 0.9822 | 0.6343 | 0.056* | 0.50 |
C27 | 0.7416 (6) | 0.9884 (5) | 0.5822 (6) | 0.109 (3) | 0.50 |
H27A | 0.7814 | 0.9674 | 0.6378 | 0.164* | 0.50 |
H27B | 0.7862 | 0.9693 | 0.5276 | 0.164* | 0.50 |
H27C | 0.7464 | 1.0445 | 0.5837 | 0.164* | 0.50 |
H4A | −0.2027 (19) | 0.3390 (12) | 0.4154 (13) | 0.042 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0137 (5) | 0.0167 (5) | 0.0298 (6) | −0.0044 (4) | −0.0008 (4) | 0.0045 (4) |
O2 | 0.0231 (6) | 0.0228 (6) | 0.0442 (7) | −0.0014 (5) | −0.0039 (5) | 0.0122 (5) |
O3 | 0.0275 (6) | 0.0284 (6) | 0.0407 (7) | −0.0014 (5) | 0.0069 (5) | 0.0149 (5) |
O4 | 0.0195 (6) | 0.0244 (6) | 0.0246 (6) | 0.0020 (4) | −0.0004 (4) | 0.0079 (5) |
O5 | 0.0170 (6) | 0.0484 (8) | 0.0328 (7) | −0.0064 (5) | −0.0009 (5) | −0.0110 (6) |
O6 | 0.0260 (7) | 0.0379 (7) | 0.0492 (8) | 0.0133 (5) | 0.0110 (6) | −0.0049 (6) |
N1 | 0.0162 (6) | 0.0161 (6) | 0.0244 (7) | −0.0043 (5) | 0.0022 (5) | −0.0010 (5) |
N2 | 0.0202 (7) | 0.0216 (7) | 0.0215 (7) | −0.0036 (5) | −0.0013 (5) | −0.0028 (5) |
N3 | 0.0178 (7) | 0.0222 (7) | 0.0223 (7) | −0.0042 (5) | 0.0000 (5) | −0.0008 (5) |
N4 | 0.0120 (7) | 0.0278 (7) | 0.0268 (7) | −0.0030 (5) | −0.0014 (5) | 0.0041 (6) |
N5 | 0.0178 (7) | 0.0295 (7) | 0.0225 (7) | 0.0037 (6) | 0.0028 (6) | 0.0005 (6) |
C1 | 0.0139 (7) | 0.0164 (7) | 0.0225 (8) | 0.0008 (6) | −0.0003 (6) | 0.0029 (6) |
C2 | 0.0138 (7) | 0.0175 (7) | 0.0224 (8) | 0.0006 (6) | −0.0032 (6) | 0.0018 (6) |
C3 | 0.0173 (8) | 0.0186 (7) | 0.0301 (9) | −0.0017 (6) | 0.0003 (6) | 0.0030 (6) |
C4 | 0.0218 (8) | 0.0247 (8) | 0.0298 (9) | 0.0011 (7) | 0.0076 (7) | 0.0038 (7) |
C5 | 0.0314 (9) | 0.0236 (8) | 0.0276 (9) | 0.0025 (7) | 0.0071 (7) | −0.0048 (7) |
C6 | 0.0261 (9) | 0.0175 (7) | 0.0295 (9) | −0.0008 (6) | 0.0021 (7) | −0.0042 (6) |
C7 | 0.0146 (7) | 0.0201 (7) | 0.0206 (8) | 0.0017 (6) | 0.0004 (6) | 0.0004 (6) |
C8 | 0.0165 (8) | 0.0221 (8) | 0.0172 (7) | −0.0002 (6) | 0.0009 (6) | 0.0000 (6) |
C9 | 0.0143 (7) | 0.0185 (7) | 0.0180 (7) | −0.0006 (6) | 0.0007 (6) | 0.0000 (6) |
C10 | 0.0139 (7) | 0.0168 (7) | 0.0185 (7) | −0.0024 (6) | −0.0011 (6) | 0.0004 (6) |
C11 | 0.0188 (8) | 0.0189 (7) | 0.0185 (7) | −0.0021 (6) | 0.0026 (6) | 0.0000 (6) |
C12 | 0.0180 (8) | 0.0217 (8) | 0.0209 (8) | −0.0035 (6) | 0.0024 (6) | −0.0001 (6) |
C13 | 0.0185 (8) | 0.0285 (9) | 0.0252 (8) | 0.0025 (7) | −0.0018 (6) | 0.0031 (7) |
C14 | 0.0198 (8) | 0.0331 (9) | 0.0337 (9) | −0.0091 (7) | 0.0003 (7) | 0.0065 (7) |
C15 | 0.0167 (8) | 0.0150 (7) | 0.0168 (7) | −0.0009 (6) | 0.0000 (6) | 0.0028 (6) |
C16 | 0.0151 (7) | 0.0164 (7) | 0.0189 (7) | −0.0014 (6) | −0.0022 (6) | 0.0000 (6) |
C17 | 0.0132 (7) | 0.0191 (7) | 0.0219 (8) | 0.0005 (6) | 0.0014 (6) | 0.0022 (6) |
C18 | 0.0276 (9) | 0.0221 (8) | 0.0230 (8) | −0.0012 (7) | 0.0047 (7) | −0.0055 (6) |
C19 | 0.0257 (9) | 0.0313 (9) | 0.0278 (9) | −0.0091 (7) | −0.0009 (7) | −0.0097 (7) |
C20 | 0.0167 (8) | 0.0276 (8) | 0.0250 (8) | −0.0069 (6) | 0.0000 (6) | −0.0017 (7) |
C21 | 0.0210 (8) | 0.0199 (7) | 0.0227 (8) | −0.0012 (6) | 0.0041 (6) | −0.0004 (6) |
C22 | 0.0291 (9) | 0.0317 (9) | 0.0313 (9) | 0.0100 (7) | 0.0026 (7) | 0.0112 (7) |
C23 | 0.0281 (10) | 0.0305 (9) | 0.0466 (11) | 0.0074 (7) | −0.0061 (8) | 0.0053 (8) |
O7 | 0.071 (2) | 0.084 (3) | 0.066 (2) | −0.011 (2) | 0.0232 (19) | 0.0087 (19) |
O8 | 0.084 (5) | 0.031 (3) | 0.029 (2) | 0.011 (3) | 0.005 (3) | 0.005 (2) |
C24 | 0.074 (7) | 0.074 (5) | 0.051 (4) | 0.013 (5) | −0.030 (4) | 0.004 (4) |
C25 | 0.096 (7) | 0.048 (4) | 0.053 (4) | 0.004 (4) | 0.016 (4) | −0.020 (3) |
C26 | 0.067 (5) | 0.037 (3) | 0.035 (3) | 0.005 (3) | −0.023 (3) | 0.008 (2) |
C27 | 0.083 (5) | 0.112 (6) | 0.132 (6) | −0.038 (4) | −0.066 (5) | 0.025 (4) |
Geometric parameters (Å, º) top
O1—N1 | 1.3718 (14) | C14—H14B | 0.9800 |
O1—C7 | 1.4326 (17) | C14—H14C | 0.9800 |
O2—C7 | 1.1991 (17) | C15—C16 | 1.3910 (19) |
O3—C21 | 1.2109 (18) | C15—C20 | 1.393 (2) |
O4—C21 | 1.3548 (18) | C16—C17 | 1.3819 (19) |
O4—C22 | 1.4514 (19) | C16—H16 | 0.9500 |
O5—N5 | 1.2346 (17) | C17—C18 | 1.382 (2) |
O6—N5 | 1.2263 (16) | C18—C19 | 1.385 (2) |
N1—N2 | 1.3448 (17) | C18—H18 | 0.9500 |
N1—C1 | 1.3608 (18) | C19—C20 | 1.387 (2) |
N2—N3 | 1.3113 (17) | C19—H19 | 0.9500 |
N3—C2 | 1.3859 (19) | C20—H20 | 0.9500 |
N4—C8 | 1.3685 (19) | C22—C23 | 1.500 (2) |
N4—C12 | 1.3872 (19) | C22—H22A | 0.9900 |
N4—H4A | 0.86 (2) | C22—H22B | 0.9900 |
N5—C17 | 1.4641 (18) | C23—H23A | 0.9800 |
C1—C6 | 1.395 (2) | C23—H23B | 0.9800 |
C1—C2 | 1.3963 (19) | C23—H23C | 0.9800 |
C2—C3 | 1.404 (2) | O7—C25 | 1.223 (8) |
C3—C4 | 1.372 (2) | O7—O8i | 1.511 (6) |
C3—H3 | 0.9500 | O8—C25i | 0.563 (9) |
C4—C5 | 1.412 (2) | O8—O8i | 0.943 (11) |
C4—H4 | 0.9500 | O8—C25 | 1.364 (6) |
C5—C6 | 1.372 (2) | O8—C26 | 1.425 (6) |
C5—H5A | 0.9500 | O8—O7i | 1.511 (6) |
C6—H6A | 0.9500 | O8—C24i | 1.835 (8) |
C7—C9 | 1.4458 (19) | C24—C26i | 0.569 (8) |
C8—C9 | 1.365 (2) | C24—C27i | 1.060 (10) |
C8—C13 | 1.504 (2) | C24—C25 | 1.519 (7) |
C9—C10 | 1.5250 (19) | C24—O8i | 1.836 (8) |
C10—C11 | 1.5221 (19) | C24—H24A | 0.9600 |
C10—C15 | 1.5335 (19) | C24—H24B | 0.9600 |
C10—H10 | 1.0000 | C24—H24C | 0.9599 |
C11—C12 | 1.355 (2) | C26—C27 | 1.532 (6) |
C11—C21 | 1.476 (2) | C26—H26A | 0.9600 |
C12—C14 | 1.501 (2) | C26—H26B | 0.9600 |
C13—H13A | 0.9800 | C27—H27A | 0.9600 |
C13—H13B | 0.9800 | C27—H27B | 0.9601 |
C13—H13C | 0.9800 | C27—H27C | 0.9600 |
C14—H14A | 0.9800 | | |
| | | |
N1—O1—C7 | 113.28 (10) | H14A—C14—H14B | 109.5 |
C21—O4—C22 | 116.73 (12) | C12—C14—H14C | 109.5 |
N2—N1—C1 | 113.42 (11) | H14A—C14—H14C | 109.5 |
N2—N1—O1 | 119.47 (11) | H14B—C14—H14C | 109.5 |
C1—N1—O1 | 126.65 (12) | C16—C15—C20 | 118.50 (13) |
N3—N2—N1 | 106.98 (11) | C16—C15—C10 | 119.91 (12) |
N2—N3—C2 | 108.40 (11) | C20—C15—C10 | 121.57 (13) |
C8—N4—C12 | 124.28 (13) | C17—C16—C15 | 118.77 (13) |
C8—N4—H4A | 116.1 (14) | C17—C16—H16 | 120.6 |
C12—N4—H4A | 118.3 (14) | C15—C16—H16 | 120.6 |
O6—N5—O5 | 123.66 (13) | C18—C17—C16 | 123.63 (14) |
O6—N5—C17 | 119.00 (13) | C18—C17—N5 | 118.88 (13) |
O5—N5—C17 | 117.33 (12) | C16—C17—N5 | 117.49 (13) |
N1—C1—C6 | 134.69 (14) | C17—C18—C19 | 117.11 (14) |
N1—C1—C2 | 101.93 (12) | C17—C18—H18 | 121.4 |
C6—C1—C2 | 123.37 (14) | C19—C18—H18 | 121.4 |
N3—C2—C1 | 109.27 (12) | C18—C19—C20 | 120.58 (14) |
N3—C2—C3 | 130.38 (13) | C18—C19—H19 | 119.7 |
C1—C2—C3 | 120.34 (14) | C20—C19—H19 | 119.7 |
C4—C3—C2 | 116.75 (14) | C19—C20—C15 | 121.40 (14) |
C4—C3—H3 | 121.6 | C19—C20—H20 | 119.3 |
C2—C3—H3 | 121.6 | C15—C20—H20 | 119.3 |
C3—C4—C5 | 121.75 (15) | O3—C21—O4 | 121.92 (14) |
C3—C4—H4 | 119.1 | O3—C21—C11 | 127.51 (15) |
C5—C4—H4 | 119.1 | O4—C21—C11 | 110.57 (12) |
C6—C5—C4 | 122.57 (15) | O4—C22—C23 | 107.37 (13) |
C6—C5—H5A | 118.7 | O4—C22—H22A | 110.2 |
C4—C5—H5A | 118.7 | C23—C22—H22A | 110.2 |
C5—C6—C1 | 115.20 (14) | O4—C22—H22B | 110.2 |
C5—C6—H6A | 122.4 | C23—C22—H22B | 110.2 |
C1—C6—H6A | 122.4 | H22A—C22—H22B | 108.5 |
O2—C7—O1 | 120.01 (13) | C22—C23—H23A | 109.5 |
O2—C7—C9 | 132.24 (14) | C22—C23—H23B | 109.5 |
O1—C7—C9 | 107.75 (12) | H23A—C23—H23B | 109.5 |
C9—C8—N4 | 118.81 (13) | C22—C23—H23C | 109.5 |
C9—C8—C13 | 126.47 (13) | H23A—C23—H23C | 109.5 |
N4—C8—C13 | 114.71 (13) | H23B—C23—H23C | 109.5 |
C8—C9—C7 | 119.38 (13) | C25—O8—C26 | 116.0 (4) |
C8—C9—C10 | 120.98 (12) | C25—C24—H24A | 109.4 |
C7—C9—C10 | 119.60 (12) | C25—C24—H24B | 108.6 |
C11—C10—C9 | 111.15 (11) | H24A—C24—H24B | 109.5 |
C11—C10—C15 | 110.52 (11) | C25—C24—H24C | 110.5 |
C9—C10—C15 | 111.52 (11) | H24A—C24—H24C | 109.5 |
C11—C10—H10 | 107.8 | H24B—C24—H24C | 109.5 |
C9—C10—H10 | 107.8 | O7—C25—O8 | 121.9 (5) |
C15—C10—H10 | 107.8 | O7—C25—C24 | 121.5 (7) |
C12—C11—C21 | 122.01 (13) | O8—C25—C24 | 116.4 (5) |
C12—C11—C10 | 120.72 (13) | O8—C26—C27 | 105.9 (5) |
C21—C11—C10 | 117.10 (13) | O8—C26—H26A | 110.3 |
C11—C12—N4 | 119.20 (13) | C27—C26—H26A | 110.3 |
C11—C12—C14 | 127.83 (14) | O8—C26—H26B | 110.0 |
N4—C12—C14 | 112.96 (13) | C27—C26—H26B | 111.6 |
C8—C13—H13A | 109.5 | H26A—C26—H26B | 108.7 |
C8—C13—H13B | 109.5 | C26—C27—H27A | 108.5 |
H13A—C13—H13B | 109.5 | C26—C27—H27B | 110.6 |
C8—C13—H13C | 109.5 | H27A—C27—H27B | 109.5 |
H13A—C13—H13C | 109.5 | C26—C27—H27C | 109.3 |
H13B—C13—H13C | 109.5 | H27A—C27—H27C | 109.5 |
C12—C14—H14A | 109.5 | H27B—C27—H27C | 109.5 |
C12—C14—H14B | 109.5 | | |
| | | |
C7—O1—N1—N2 | 92.51 (14) | C9—C10—C11—C12 | 21.75 (19) |
C7—O1—N1—C1 | −95.77 (16) | C15—C10—C11—C12 | −102.63 (16) |
C1—N1—N2—N3 | 0.68 (16) | C9—C10—C11—C21 | −162.93 (12) |
O1—N1—N2—N3 | 173.44 (11) | C15—C10—C11—C21 | 72.69 (16) |
N1—N2—N3—C2 | −0.53 (15) | C21—C11—C12—N4 | 177.88 (13) |
N2—N1—C1—C6 | −178.83 (16) | C10—C11—C12—N4 | −7.0 (2) |
O1—N1—C1—C6 | 9.0 (3) | C21—C11—C12—C14 | −3.0 (2) |
N2—N1—C1—C2 | −0.51 (16) | C10—C11—C12—C14 | 172.11 (14) |
O1—N1—C1—C2 | −172.66 (12) | C8—N4—C12—C11 | −11.4 (2) |
N2—N3—C2—C1 | 0.22 (17) | C8—N4—C12—C14 | 169.32 (14) |
N2—N3—C2—C3 | 179.30 (15) | C11—C10—C15—C16 | −131.81 (14) |
N1—C1—C2—N3 | 0.17 (15) | C9—C10—C15—C16 | 104.02 (15) |
C6—C1—C2—N3 | 178.74 (13) | C11—C10—C15—C20 | 46.58 (18) |
N1—C1—C2—C3 | −179.01 (13) | C9—C10—C15—C20 | −77.59 (16) |
C6—C1—C2—C3 | −0.4 (2) | C20—C15—C16—C17 | −0.1 (2) |
N3—C2—C3—C4 | −177.63 (15) | C10—C15—C16—C17 | 178.34 (13) |
C1—C2—C3—C4 | 1.4 (2) | C15—C16—C17—C18 | −0.9 (2) |
C2—C3—C4—C5 | −1.1 (2) | C15—C16—C17—N5 | 179.83 (12) |
C3—C4—C5—C6 | −0.1 (3) | O6—N5—C17—C18 | −17.2 (2) |
C4—C5—C6—C1 | 1.0 (2) | O5—N5—C17—C18 | 162.03 (14) |
N1—C1—C6—C5 | 177.27 (16) | O6—N5—C17—C16 | 162.08 (14) |
C2—C1—C6—C5 | −0.8 (2) | O5—N5—C17—C16 | −18.70 (19) |
N1—O1—C7—O2 | −1.81 (19) | C16—C17—C18—C19 | 1.4 (2) |
N1—O1—C7—C9 | 178.20 (11) | N5—C17—C18—C19 | −179.36 (13) |
C12—N4—C8—C9 | 11.8 (2) | C17—C18—C19—C20 | −0.9 (2) |
C12—N4—C8—C13 | −167.30 (14) | C18—C19—C20—C15 | −0.1 (2) |
N4—C8—C9—C7 | −176.15 (13) | C16—C15—C20—C19 | 0.6 (2) |
C13—C8—C9—C7 | 2.8 (2) | C10—C15—C20—C19 | −177.83 (14) |
N4—C8—C9—C10 | 6.2 (2) | C22—O4—C21—O3 | 0.1 (2) |
C13—C8—C9—C10 | −174.85 (13) | C22—O4—C21—C11 | −179.99 (12) |
O2—C7—C9—C8 | −5.9 (3) | C12—C11—C21—O3 | −5.5 (2) |
O1—C7—C9—C8 | 174.07 (12) | C10—C11—C21—O3 | 179.21 (15) |
O2—C7—C9—C10 | 171.77 (16) | C12—C11—C21—O4 | 174.51 (13) |
O1—C7—C9—C10 | −8.24 (17) | C10—C11—C21—O4 | −0.75 (18) |
C8—C9—C10—C11 | −21.40 (18) | C21—O4—C22—C23 | 177.13 (13) |
C7—C9—C10—C11 | 160.95 (13) | C26—O8—C25—O7 | −0.1 (9) |
C8—C9—C10—C15 | 102.41 (15) | C26—O8—C25—C24 | 174.9 (11) |
C7—C9—C10—C15 | −75.24 (16) | C25—O8—C26—C27 | −174.1 (6) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4A···O5ii | 0.86 (2) | 2.17 (2) | 2.9770 (18) | 157.4 (18) |
Symmetry code: (ii) x−1, y, z. |
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