Erlotinib is a BCS (biopharmaceutical classification system) class II drug used for the treatment of non-small cell lung cancer. There is an urgent need to obtain new solid forms of higher solubility to improve the bioavailability of the API (active pharmaceutical ingredient). In this context, cocrystals with urea, succinic acid, and glutaric acid and salts with maleic acid, adipic acid, and saccharin were prepared
via wet granulation and solution crystallizations. Crystal structures of the free base (
Z′ = 2), cocrystals of erlotinib–urea (1:1), erlotinib–succinic acid monohydrate (1:1:1), erlotinib–glutaric acid monohydrate (1:1:1) and salts of erlotinib–adipic acid adipate (1:0.5:0.5) are determined and their hydrogen-bonding patterns are analyzed. Self recognition
via the (amine) N—H
N (pyridine) hydrogen bond between the API molecules is replaced by several heterosynthons such as acid–pyridine, amide–pyridine and carboxylate–pyridinium in the new binary systems. Auxiliary interactions play an important role in determining the conformation of the API in the crystal. FT–IR spectroscopy is used to distinguish between the salts and cocrystals in the new multi-component systems. The new solid forms are characterized by powder X-ray diffraction (PXRD) and differential scanning calorimetry (DSC) to confirm their unique phase identity.
Supporting information
CCDC references: 1051785; 1051786; 1051787; 1051788; 1430934
For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
Crystal data top
C22H23N3O4 | F(000) = 832 |
Mr = 393.43 | Dx = 1.307 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.966 (5) Å | Cell parameters from 5484 reflections |
b = 12.991 (4) Å | θ = 2.4–27.5° |
c = 11.225 (4) Å | µ = 0.09 mm−1 |
β = 100.931 (16)° | T = 150 K |
V = 1999.6 (11) Å3 | Plate, colorless |
Z = 4 | 0.40 × 0.10 × 0.08 mm |
Data collection top
XtaLABmini diffractometer | 7841 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.153 |
Graphite monochromator | θmax = 27.8°, θmin = 1.5° |
Absorption correction: multi-scan SADABS | h = −18→18 |
Tmin = 0.769, Tmax = 1.000 | k = −16→16 |
20777 measured reflections | l = −14→14 |
9220 independent 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)] = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.235 | w = 1/[σ2(Fo2) + (0.1306P)2 + 0.1558P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
9220 reflections | Δρmax = 0.45 e Å−3 |
535 parameters | Δρmin = −0.55 e Å−3 |
2 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −2.0 (12) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
O5 | 0.62474 (19) | 0.3201 (2) | 0.6791 (2) | 0.0262 (5) | |
O8 | 0.69754 (19) | 0.6536 (2) | 0.7621 (2) | 0.0293 (6) | |
O7 | 0.56848 (19) | 0.50326 (19) | 0.6648 (2) | 0.0266 (6) | |
N5 | 0.2473 (2) | 0.3410 (2) | 0.2628 (3) | 0.0244 (6) | |
C34 | 0.3812 (2) | 0.3932 (3) | 0.4202 (3) | 0.0194 (6) | |
C37 | 0.5435 (3) | 0.3351 (3) | 0.5939 (3) | 0.0210 (6) | |
N6 | 0.3532 (2) | 0.2134 (2) | 0.3700 (3) | 0.0243 (6) | |
N4 | 0.2699 (2) | 0.5134 (2) | 0.3019 (3) | 0.0218 (6) | |
C39 | 0.6614 (3) | 0.2178 (3) | 0.7023 (4) | 0.0270 (7) | |
H39A | 0.6831 | 0.1903 | 0.6316 | 0.032* | |
H39B | 0.6111 | 0.1730 | 0.7222 | 0.032* | |
C35 | 0.4352 (2) | 0.4686 (3) | 0.4956 (3) | 0.0215 (7) | |
H35 | 0.4174 | 0.5376 | 0.4863 | 0.026* | |
C31 | 0.2985 (2) | 0.4159 (3) | 0.3273 (3) | 0.0199 (6) | |
C29 | 0.1873 (3) | 0.5413 (3) | 0.2102 (3) | 0.0218 (6) | |
C33 | 0.4071 (2) | 0.2891 (3) | 0.4377 (3) | 0.0209 (7) | |
C36 | 0.5133 (2) | 0.4405 (2) | 0.5816 (3) | 0.0198 (6) | |
C26 | 0.0289 (3) | 0.6031 (3) | 0.0362 (3) | 0.0279 (7) | |
H26 | −0.0239 | 0.6232 | −0.0228 | 0.033* | |
C24 | −0.0842 (3) | 0.5428 (3) | 0.1645 (4) | 0.0297 (8) | |
C28 | 0.2024 (3) | 0.5876 (3) | 0.1050 (3) | 0.0252 (7) | |
H28 | 0.2655 | 0.5982 | 0.0922 | 0.030* | |
C32 | 0.2783 (3) | 0.2443 (3) | 0.2905 (3) | 0.0277 (7) | |
H32 | 0.2412 | 0.1925 | 0.2469 | 0.033* | |
C25 | 0.0135 (3) | 0.5579 (3) | 0.1422 (3) | 0.0250 (7) | |
C38 | 0.4898 (3) | 0.2612 (3) | 0.5244 (3) | 0.0214 (7) | |
H38 | 0.5080 | 0.1924 | 0.5343 | 0.026* | |
O6 | 0.7178 (3) | 0.2450 (3) | 0.9204 (3) | 0.0459 (8) | |
C27 | 0.1228 (3) | 0.6184 (3) | 0.0177 (3) | 0.0283 (8) | |
H27 | 0.1330 | 0.6495 | −0.0534 | 0.034* | |
C43 | 0.6025 (3) | 0.6500 (3) | 0.7856 (3) | 0.0246 (7) | |
H43A | 0.5809 | 0.7186 | 0.8022 | 0.030* | |
H43B | 0.6006 | 0.6069 | 0.8557 | 0.030* | |
C42 | 0.5374 (3) | 0.6062 (3) | 0.6753 (3) | 0.0250 (7) | |
H42A | 0.4698 | 0.6079 | 0.6848 | 0.030* | |
H42B | 0.5435 | 0.6455 | 0.6036 | 0.030* | |
C30 | 0.0936 (3) | 0.5265 (3) | 0.2300 (3) | 0.0241 (7) | |
H30 | 0.0836 | 0.4958 | 0.3015 | 0.029* | |
C23 | −0.1640 (3) | 0.5287 (4) | 0.1812 (4) | 0.0350 (9) | |
H23 | −0.2269 | 0.5176 | 0.1944 | 0.042* | |
C44 | 0.7683 (4) | 0.6819 (4) | 0.8663 (4) | 0.0449 (11) | |
H44A | 0.7782 | 0.6255 | 0.9226 | 0.067* | |
H44B | 0.7454 | 0.7408 | 0.9044 | 0.067* | |
H44C | 0.8287 | 0.6985 | 0.8420 | 0.067* | |
C41 | 0.7100 (4) | 0.3506 (4) | 0.9494 (4) | 0.0491 (12) | |
H41A | 0.6516 | 0.3787 | 0.9014 | 0.074* | |
H41B | 0.7656 | 0.3872 | 0.9325 | 0.074* | |
H41C | 0.7075 | 0.3573 | 1.0339 | 0.074* | |
C40 | 0.7466 (3) | 0.2255 (3) | 0.8091 (4) | 0.0309 (8) | |
H40A | 0.7831 | 0.1616 | 0.8155 | 0.037* | |
H40B | 0.7898 | 0.2802 | 0.7932 | 0.037* | |
O1 | 0.0848 (2) | 0.1824 (2) | 1.0454 (3) | 0.0284 (6) | |
O3 | 0.1411 (2) | −0.0018 (2) | 1.0589 (3) | 0.0292 (6) | |
N3 | 0.3584 (2) | 0.2876 (2) | 0.8724 (3) | 0.0246 (6) | |
N1 | 0.4377 (2) | −0.0133 (2) | 0.8381 (3) | 0.0239 (6) | |
C15 | 0.1666 (3) | 0.1660 (3) | 1.0016 (3) | 0.0218 (7) | |
C11 | 0.3039 (3) | 0.2114 (3) | 0.9118 (3) | 0.0200 (6) | |
C14 | 0.1959 (3) | 0.0605 (3) | 1.0037 (3) | 0.0229 (7) | |
N2 | 0.4627 (2) | 0.1591 (2) | 0.8153 (3) | 0.0261 (6) | |
C16 | 0.2208 (3) | 0.2398 (3) | 0.9588 (3) | 0.0245 (7) | |
H16 | 0.2030 | 0.3087 | 0.9605 | 0.029* | |
C5 | 0.5219 (3) | −0.0400 (3) | 0.7896 (3) | 0.0220 (7) | |
C13 | 0.2738 (2) | 0.0317 (3) | 0.9550 (3) | 0.0221 (7) | |
H13 | 0.2910 | −0.0374 | 0.9536 | 0.026* | |
O4 | 0.0155 (2) | −0.1522 (2) | 1.1064 (3) | 0.0338 (6) | |
C17 | 0.0490 (3) | 0.2862 (3) | 1.0470 (4) | 0.0276 (8) | |
H17A | 0.0309 | 0.3126 | 0.9650 | 0.033* | |
H17B | 0.0988 | 0.3306 | 1.0923 | 0.033* | |
C10 | 0.4335 (3) | 0.2559 (3) | 0.8285 (3) | 0.0266 (7) | |
H10 | 0.4716 | 0.3073 | 0.8033 | 0.032* | |
C4 | 0.6145 (3) | −0.0211 (3) | 0.8566 (3) | 0.0259 (7) | |
H4 | 0.6218 | 0.0110 | 0.9319 | 0.031* | |
C12 | 0.3286 (2) | 0.1071 (3) | 0.9065 (3) | 0.0210 (7) | |
C9 | 0.4111 (2) | 0.0848 (3) | 0.8530 (3) | 0.0197 (6) | |
C20 | 0.1741 (3) | −0.1054 (3) | 1.0834 (3) | 0.0256 (7) | |
H20A | 0.2425 | −0.1065 | 1.1213 | 0.031* | |
H20B | 0.1655 | −0.1451 | 1.0089 | 0.031* | |
O2 | −0.0140 (3) | 0.2689 (3) | 1.2335 (3) | 0.0502 (9) | |
C3 | 0.6969 (3) | −0.0503 (3) | 0.8109 (3) | 0.0267 (7) | |
C8 | 0.6848 (3) | −0.0988 (3) | 0.6987 (4) | 0.0303 (8) | |
H8 | 0.7390 | −0.1179 | 0.6669 | 0.036* | |
C2 | 0.7926 (3) | −0.0314 (3) | 0.8824 (4) | 0.0357 (9) | |
C21 | 0.1129 (3) | −0.1483 (3) | 1.1671 (3) | 0.0274 (7) | |
H21A | 0.1354 | −0.2168 | 1.1929 | 0.033* | |
H21B | 0.1184 | −0.1050 | 1.2385 | 0.033* | |
C6 | 0.5100 (3) | −0.0898 (3) | 0.6790 (3) | 0.0286 (7) | |
H6 | 0.4478 | −0.1036 | 0.6353 | 0.034* | |
C18 | −0.0386 (3) | 0.2825 (3) | 1.1070 (4) | 0.0359 (9) | |
H18A | −0.0751 | 0.3460 | 1.0899 | 0.043* | |
H18B | −0.0806 | 0.2263 | 1.0722 | 0.043* | |
C22 | −0.0489 (4) | −0.1753 (4) | 1.1833 (5) | 0.0466 (11) | |
H22A | −0.0463 | −0.1219 | 1.2428 | 0.070* | |
H22B | −0.0308 | −0.2397 | 1.2232 | 0.070* | |
H22C | −0.1139 | −0.1803 | 1.1368 | 0.070* | |
C7 | 0.5915 (3) | −0.1187 (3) | 0.6340 (3) | 0.0310 (8) | |
H7 | 0.5838 | −0.1519 | 0.5594 | 0.037* | |
C1 | 0.8711 (3) | −0.0140 (4) | 0.9415 (4) | 0.0428 (11) | |
H1 | 0.9324 | −0.0003 | 0.9877 | 0.051* | |
C19 | −0.0046 (5) | 0.1672 (5) | 1.2737 (5) | 0.0583 (14) | |
H19A | 0.0571 | 0.1404 | 1.2624 | 0.087* | |
H19B | −0.0563 | 0.1266 | 1.2282 | 0.087* | |
H19C | −0.0081 | 0.1647 | 1.3583 | 0.087* | |
H1N | 0.414 (2) | −0.072 (3) | 0.862 (3) | 0.000 (7)* | |
H4N | 0.301 (4) | 0.555 (4) | 0.324 (5) | 0.033 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0238 (13) | 0.0197 (12) | 0.0300 (12) | 0.0045 (10) | −0.0079 (10) | 0.0034 (10) |
O8 | 0.0194 (13) | 0.0313 (14) | 0.0339 (13) | −0.0002 (11) | −0.0033 (10) | −0.0057 (11) |
O7 | 0.0233 (13) | 0.0170 (12) | 0.0326 (13) | 0.0032 (9) | −0.0120 (10) | −0.0050 (9) |
N5 | 0.0221 (14) | 0.0193 (14) | 0.0278 (14) | 0.0013 (12) | −0.0057 (11) | −0.0064 (11) |
C34 | 0.0169 (15) | 0.0155 (15) | 0.0245 (15) | 0.0018 (12) | 0.0003 (12) | −0.0019 (12) |
C37 | 0.0198 (15) | 0.0179 (15) | 0.0232 (15) | −0.0001 (13) | −0.0009 (12) | 0.0019 (12) |
N6 | 0.0261 (15) | 0.0158 (13) | 0.0284 (14) | 0.0011 (12) | −0.0017 (12) | −0.0036 (11) |
N4 | 0.0149 (14) | 0.0159 (14) | 0.0302 (14) | 0.0023 (12) | −0.0068 (11) | −0.0011 (12) |
C39 | 0.0219 (18) | 0.0197 (17) | 0.0375 (19) | 0.0035 (13) | 0.0008 (14) | 0.0065 (14) |
C35 | 0.0201 (16) | 0.0141 (15) | 0.0282 (16) | 0.0007 (12) | −0.0011 (13) | −0.0003 (12) |
C31 | 0.0196 (15) | 0.0165 (16) | 0.0218 (14) | 0.0012 (12) | −0.0003 (12) | 0.0012 (12) |
C29 | 0.0202 (15) | 0.0170 (15) | 0.0254 (15) | 0.0026 (13) | −0.0023 (12) | −0.0024 (12) |
C33 | 0.0196 (16) | 0.0186 (16) | 0.0236 (15) | 0.0013 (12) | 0.0016 (13) | 0.0008 (12) |
C36 | 0.0198 (15) | 0.0137 (15) | 0.0229 (15) | −0.0008 (12) | −0.0036 (12) | −0.0008 (12) |
C26 | 0.0260 (18) | 0.0255 (18) | 0.0274 (17) | 0.0030 (14) | −0.0073 (14) | −0.0011 (14) |
C24 | 0.0227 (17) | 0.0254 (19) | 0.0384 (19) | 0.0044 (14) | −0.0012 (14) | −0.0008 (15) |
C28 | 0.0236 (16) | 0.0224 (17) | 0.0294 (17) | 0.0020 (14) | 0.0043 (14) | 0.0016 (14) |
C32 | 0.0287 (18) | 0.0172 (16) | 0.0329 (18) | −0.0009 (14) | −0.0051 (14) | −0.0021 (14) |
C25 | 0.0214 (17) | 0.0203 (16) | 0.0312 (17) | 0.0007 (13) | −0.0002 (13) | −0.0030 (13) |
C38 | 0.0227 (16) | 0.0148 (15) | 0.0254 (15) | 0.0030 (13) | 0.0013 (13) | 0.0009 (12) |
O6 | 0.0447 (19) | 0.058 (2) | 0.0309 (14) | −0.0141 (17) | −0.0034 (13) | 0.0107 (14) |
C27 | 0.033 (2) | 0.0275 (19) | 0.0235 (16) | 0.0025 (15) | 0.0033 (14) | 0.0030 (13) |
C43 | 0.0277 (18) | 0.0204 (16) | 0.0245 (16) | −0.0014 (14) | 0.0018 (13) | −0.0058 (13) |
C42 | 0.0214 (17) | 0.0190 (17) | 0.0318 (17) | 0.0035 (13) | −0.0025 (13) | −0.0040 (13) |
C30 | 0.0227 (17) | 0.0209 (16) | 0.0274 (16) | 0.0023 (13) | 0.0013 (13) | 0.0018 (13) |
C23 | 0.0195 (18) | 0.038 (2) | 0.046 (2) | −0.0032 (16) | 0.0029 (16) | −0.0035 (18) |
C44 | 0.040 (3) | 0.041 (3) | 0.044 (2) | −0.004 (2) | −0.016 (2) | 0.001 (2) |
C41 | 0.043 (3) | 0.064 (3) | 0.038 (2) | 0.006 (2) | 0.0008 (19) | −0.007 (2) |
C40 | 0.0206 (17) | 0.033 (2) | 0.0359 (19) | −0.0002 (15) | −0.0025 (15) | 0.0087 (16) |
O1 | 0.0253 (13) | 0.0189 (13) | 0.0427 (14) | 0.0036 (10) | 0.0111 (11) | 0.0014 (11) |
O3 | 0.0260 (14) | 0.0174 (12) | 0.0471 (16) | 0.0034 (10) | 0.0148 (12) | 0.0084 (11) |
N3 | 0.0247 (15) | 0.0152 (13) | 0.0330 (15) | 0.0016 (11) | 0.0032 (12) | 0.0030 (11) |
N1 | 0.0197 (15) | 0.0166 (14) | 0.0364 (16) | 0.0014 (11) | 0.0083 (12) | 0.0026 (12) |
C15 | 0.0194 (16) | 0.0225 (17) | 0.0227 (15) | 0.0037 (13) | 0.0018 (12) | −0.0011 (13) |
C11 | 0.0217 (16) | 0.0143 (15) | 0.0211 (14) | −0.0001 (12) | −0.0033 (12) | 0.0012 (12) |
C14 | 0.0223 (16) | 0.0187 (16) | 0.0263 (16) | 0.0000 (13) | 0.0010 (12) | 0.0044 (13) |
N2 | 0.0251 (15) | 0.0182 (14) | 0.0352 (16) | 0.0000 (12) | 0.0065 (12) | 0.0016 (12) |
C16 | 0.0306 (19) | 0.0168 (16) | 0.0246 (16) | 0.0034 (14) | 0.0015 (14) | 0.0007 (12) |
C5 | 0.0194 (16) | 0.0133 (15) | 0.0339 (17) | 0.0017 (12) | 0.0061 (13) | 0.0029 (13) |
C13 | 0.0188 (16) | 0.0160 (16) | 0.0294 (16) | 0.0008 (12) | −0.0007 (13) | −0.0001 (12) |
O4 | 0.0253 (14) | 0.0355 (16) | 0.0401 (15) | −0.0012 (11) | 0.0050 (11) | 0.0103 (12) |
C17 | 0.0207 (17) | 0.0213 (17) | 0.0390 (19) | 0.0047 (14) | 0.0016 (15) | −0.0063 (14) |
C10 | 0.0269 (18) | 0.0171 (16) | 0.0370 (18) | −0.0020 (14) | 0.0089 (14) | 0.0040 (14) |
C4 | 0.0254 (18) | 0.0202 (16) | 0.0310 (17) | 0.0034 (14) | 0.0031 (14) | −0.0033 (13) |
C12 | 0.0183 (15) | 0.0181 (16) | 0.0244 (15) | 0.0020 (12) | −0.0017 (12) | 0.0011 (12) |
C9 | 0.0188 (15) | 0.0166 (15) | 0.0216 (14) | 0.0009 (12) | −0.0017 (11) | −0.0002 (11) |
C20 | 0.0242 (17) | 0.0164 (16) | 0.0351 (18) | 0.0046 (13) | 0.0030 (14) | 0.0050 (13) |
O2 | 0.051 (2) | 0.056 (2) | 0.0467 (18) | −0.0124 (17) | 0.0175 (16) | −0.0181 (16) |
C3 | 0.0213 (17) | 0.0206 (17) | 0.0371 (19) | 0.0037 (13) | 0.0031 (14) | 0.0031 (14) |
C8 | 0.0318 (19) | 0.0281 (19) | 0.0336 (19) | 0.0062 (16) | 0.0127 (15) | 0.0034 (15) |
C2 | 0.0243 (19) | 0.031 (2) | 0.052 (2) | 0.0107 (16) | 0.0061 (17) | 0.0058 (18) |
C21 | 0.0288 (19) | 0.0245 (18) | 0.0265 (16) | −0.0008 (15) | −0.0010 (14) | 0.0026 (14) |
C6 | 0.0276 (18) | 0.0222 (17) | 0.0331 (18) | 0.0006 (14) | −0.0018 (14) | 0.0023 (14) |
C18 | 0.0192 (17) | 0.032 (2) | 0.056 (2) | 0.0023 (15) | 0.0047 (17) | −0.0108 (18) |
C22 | 0.044 (3) | 0.039 (3) | 0.061 (3) | −0.005 (2) | 0.022 (2) | 0.009 (2) |
C7 | 0.044 (2) | 0.0222 (18) | 0.0261 (17) | 0.0035 (16) | 0.0042 (16) | 0.0004 (14) |
C1 | 0.028 (2) | 0.040 (2) | 0.055 (3) | 0.0096 (18) | −0.0055 (19) | 0.003 (2) |
C19 | 0.054 (3) | 0.073 (4) | 0.050 (3) | −0.006 (3) | 0.013 (2) | 0.008 (3) |
Geometric parameters (Å, º) top
O5—C37 | 1.352 (4) | O1—C15 | 1.343 (4) |
O5—C39 | 1.431 (4) | O1—C17 | 1.440 (4) |
O8—C43 | 1.402 (4) | O3—C14 | 1.342 (4) |
O8—C44 | 1.428 (5) | O3—C20 | 1.433 (4) |
O7—C36 | 1.362 (4) | N3—C10 | 1.307 (5) |
O7—C42 | 1.418 (4) | N3—C11 | 1.372 (5) |
N5—C31 | 1.336 (4) | N1—C9 | 1.347 (4) |
N5—C32 | 1.346 (5) | N1—C5 | 1.429 (4) |
C34—C33 | 1.403 (5) | N1—H1N | 0.89 (3) |
C34—C35 | 1.416 (5) | C15—C16 | 1.364 (5) |
C34—C31 | 1.431 (4) | C15—C14 | 1.429 (5) |
C37—C38 | 1.369 (5) | C11—C12 | 1.402 (5) |
C37—C36 | 1.431 (4) | C11—C16 | 1.411 (5) |
N6—C32 | 1.303 (5) | C14—C13 | 1.360 (5) |
N6—C33 | 1.377 (4) | N2—C9 | 1.322 (5) |
N4—C31 | 1.343 (4) | N2—C10 | 1.340 (5) |
N4—C29 | 1.439 (4) | C16—H16 | 0.9300 |
N4—H4N | 0.71 (6) | C5—C6 | 1.382 (5) |
C39—C40 | 1.524 (5) | C5—C4 | 1.390 (5) |
C39—H39A | 0.9700 | C13—C12 | 1.414 (5) |
C39—H39B | 0.9700 | C13—H13 | 0.9300 |
C35—C36 | 1.362 (5) | O4—C22 | 1.392 (5) |
C35—H35 | 0.9300 | O4—C21 | 1.402 (5) |
C29—C28 | 1.377 (5) | C17—C18 | 1.505 (5) |
C29—C30 | 1.381 (5) | C17—H17A | 0.9700 |
C33—C38 | 1.410 (5) | C17—H17B | 0.9700 |
C26—C25 | 1.380 (5) | C10—H10 | 0.9300 |
C26—C27 | 1.380 (6) | C4—C3 | 1.398 (5) |
C26—H26 | 0.9300 | C4—H4 | 0.9300 |
C24—C23 | 1.179 (6) | C12—C9 | 1.427 (4) |
C24—C25 | 1.446 (5) | C20—C21 | 1.492 (5) |
C28—C27 | 1.394 (5) | C20—H20A | 0.9700 |
C28—H28 | 0.9300 | C20—H20B | 0.9700 |
C32—H32 | 0.9300 | O2—C19 | 1.394 (8) |
C25—C30 | 1.405 (5) | O2—C18 | 1.408 (6) |
C38—H38 | 0.9300 | C3—C8 | 1.390 (6) |
O6—C40 | 1.407 (5) | C3—C2 | 1.444 (6) |
O6—C41 | 1.418 (7) | C8—C7 | 1.390 (6) |
C27—H27 | 0.9300 | C8—H8 | 0.9300 |
C43—C42 | 1.502 (5) | C2—C1 | 1.190 (6) |
C43—H43A | 0.9700 | C21—H21A | 0.9700 |
C43—H43B | 0.9700 | C21—H21B | 0.9700 |
C42—H42A | 0.9700 | C6—C7 | 1.382 (6) |
C42—H42B | 0.9700 | C6—H6 | 0.9300 |
C30—H30 | 0.9300 | C18—H18A | 0.9700 |
C23—H23 | 0.9300 | C18—H18B | 0.9700 |
C44—H44A | 0.9600 | C22—H22A | 0.9600 |
C44—H44B | 0.9600 | C22—H22B | 0.9600 |
C44—H44C | 0.9600 | C22—H22C | 0.9600 |
C41—H41A | 0.9600 | C7—H7 | 0.9300 |
C41—H41B | 0.9600 | C1—H1 | 0.9300 |
C41—H41C | 0.9600 | C19—H19A | 0.9600 |
C40—H40A | 0.9700 | C19—H19B | 0.9600 |
C40—H40B | 0.9700 | C19—H19C | 0.9600 |
| | | |
C37—O5—C39 | 119.1 (3) | C15—O1—C17 | 118.3 (3) |
C43—O8—C44 | 112.8 (3) | C14—O3—C20 | 117.7 (3) |
C36—O7—C42 | 118.6 (3) | C10—N3—C11 | 115.4 (3) |
C31—N5—C32 | 116.0 (3) | C9—N1—C5 | 122.9 (3) |
C33—C34—C35 | 119.3 (3) | C9—N1—H1N | 130 (2) |
C33—C34—C31 | 116.8 (3) | C5—N1—H1N | 107 (2) |
C35—C34—C31 | 123.9 (3) | O1—C15—C16 | 125.8 (3) |
O5—C37—C38 | 126.7 (3) | O1—C15—C14 | 113.9 (3) |
O5—C37—C36 | 113.5 (3) | C16—C15—C14 | 120.2 (3) |
C38—C37—C36 | 119.8 (3) | N3—C11—C12 | 121.8 (3) |
C32—N6—C33 | 116.1 (3) | N3—C11—C16 | 118.6 (3) |
C31—N4—C29 | 123.7 (3) | C12—C11—C16 | 119.6 (3) |
C31—N4—H4N | 121 (4) | O3—C14—C13 | 126.1 (3) |
C29—N4—H4N | 114 (4) | O3—C14—C15 | 113.5 (3) |
O5—C39—C40 | 106.3 (3) | C13—C14—C15 | 120.3 (3) |
O5—C39—H39A | 110.5 | C9—N2—C10 | 117.0 (3) |
C40—C39—H39A | 110.5 | C15—C16—C11 | 119.9 (3) |
O5—C39—H39B | 110.5 | C15—C16—H16 | 120.0 |
C40—C39—H39B | 110.5 | C11—C16—H16 | 120.0 |
H39A—C39—H39B | 108.7 | C6—C5—C4 | 120.7 (3) |
C36—C35—C34 | 120.2 (3) | C6—C5—N1 | 119.3 (3) |
C36—C35—H35 | 119.9 | C4—C5—N1 | 120.0 (3) |
C34—C35—H35 | 119.9 | C14—C13—C12 | 119.8 (3) |
N5—C31—N4 | 117.7 (3) | C14—C13—H13 | 120.1 |
N5—C31—C34 | 121.3 (3) | C12—C13—H13 | 120.1 |
N4—C31—C34 | 121.0 (3) | C22—O4—C21 | 112.9 (3) |
C28—C29—C30 | 120.2 (3) | O1—C17—C18 | 106.8 (3) |
C28—C29—N4 | 119.4 (3) | O1—C17—H17A | 110.4 |
C30—C29—N4 | 120.3 (3) | C18—C17—H17A | 110.4 |
N6—C33—C34 | 120.8 (3) | O1—C17—H17B | 110.4 |
N6—C33—C38 | 119.1 (3) | C18—C17—H17B | 110.4 |
C34—C33—C38 | 120.1 (3) | H17A—C17—H17B | 108.6 |
C35—C36—O7 | 126.7 (3) | N3—C10—N2 | 128.3 (3) |
C35—C36—C37 | 120.4 (3) | N3—C10—H10 | 115.8 |
O7—C36—C37 | 112.8 (3) | N2—C10—H10 | 115.8 |
C25—C26—C27 | 119.9 (3) | C5—C4—C3 | 120.0 (3) |
C25—C26—H26 | 120.0 | C5—C4—H4 | 120.0 |
C27—C26—H26 | 120.0 | C3—C4—H4 | 120.0 |
C23—C24—C25 | 178.7 (5) | C11—C12—C13 | 119.8 (3) |
C29—C28—C27 | 119.8 (3) | C11—C12—C9 | 116.1 (3) |
C29—C28—H28 | 120.1 | C13—C12—C9 | 124.1 (3) |
C27—C28—H28 | 120.1 | N2—C9—N1 | 118.1 (3) |
N6—C32—N5 | 128.9 (3) | N2—C9—C12 | 121.3 (3) |
N6—C32—H32 | 115.6 | N1—C9—C12 | 120.6 (3) |
N5—C32—H32 | 115.6 | O3—C20—C21 | 105.7 (3) |
C26—C25—C30 | 119.6 (3) | O3—C20—H20A | 110.6 |
C26—C25—C24 | 120.9 (3) | C21—C20—H20A | 110.6 |
C30—C25—C24 | 119.4 (3) | O3—C20—H20B | 110.6 |
C37—C38—C33 | 120.1 (3) | C21—C20—H20B | 110.6 |
C37—C38—H38 | 120.0 | H20A—C20—H20B | 108.7 |
C33—C38—H38 | 120.0 | C19—O2—C18 | 115.8 (4) |
C40—O6—C41 | 115.2 (4) | C8—C3—C4 | 119.3 (4) |
C26—C27—C28 | 120.5 (3) | C8—C3—C2 | 121.4 (4) |
C26—C27—H27 | 119.8 | C4—C3—C2 | 119.3 (3) |
C28—C27—H27 | 119.8 | C7—C8—C3 | 119.9 (3) |
O8—C43—C42 | 107.7 (3) | C7—C8—H8 | 120.0 |
O8—C43—H43A | 110.2 | C3—C8—H8 | 120.0 |
C42—C43—H43A | 110.2 | C1—C2—C3 | 178.8 (5) |
O8—C43—H43B | 110.2 | O4—C21—C20 | 109.1 (3) |
C42—C43—H43B | 110.2 | O4—C21—H21A | 109.9 |
H43A—C43—H43B | 108.5 | C20—C21—H21A | 109.9 |
O7—C42—C43 | 106.2 (3) | O4—C21—H21B | 109.9 |
O7—C42—H42A | 110.5 | C20—C21—H21B | 109.9 |
C43—C42—H42A | 110.5 | H21A—C21—H21B | 108.3 |
O7—C42—H42B | 110.5 | C7—C6—C5 | 119.3 (4) |
C43—C42—H42B | 110.5 | C7—C6—H6 | 120.4 |
H42A—C42—H42B | 108.7 | C5—C6—H6 | 120.4 |
C29—C30—C25 | 120.0 (3) | O2—C18—C17 | 113.1 (3) |
C29—C30—H30 | 120.0 | O2—C18—H18A | 109.0 |
C25—C30—H30 | 120.0 | C17—C18—H18A | 109.0 |
C24—C23—H23 | 180.0 | O2—C18—H18B | 109.0 |
O8—C44—H44A | 109.5 | C17—C18—H18B | 109.0 |
O8—C44—H44B | 109.5 | H18A—C18—H18B | 107.8 |
H44A—C44—H44B | 109.5 | O4—C22—H22A | 109.5 |
O8—C44—H44C | 109.5 | O4—C22—H22B | 109.5 |
H44A—C44—H44C | 109.5 | H22A—C22—H22B | 109.5 |
H44B—C44—H44C | 109.5 | O4—C22—H22C | 109.5 |
O6—C41—H41A | 109.5 | H22A—C22—H22C | 109.5 |
O6—C41—H41B | 109.5 | H22B—C22—H22C | 109.5 |
H41A—C41—H41B | 109.5 | C6—C7—C8 | 120.9 (3) |
O6—C41—H41C | 109.5 | C6—C7—H7 | 119.5 |
H41A—C41—H41C | 109.5 | C8—C7—H7 | 119.5 |
H41B—C41—H41C | 109.5 | C2—C1—H1 | 180.0 |
O6—C40—C39 | 113.5 (3) | O2—C19—H19A | 109.5 |
O6—C40—H40A | 108.9 | O2—C19—H19B | 109.5 |
C39—C40—H40A | 108.9 | H19A—C19—H19B | 109.5 |
O6—C40—H40B | 108.9 | O2—C19—H19C | 109.5 |
C39—C40—H40B | 108.9 | H19A—C19—H19C | 109.5 |
H40A—C40—H40B | 107.7 | H19B—C19—H19C | 109.5 |
(Erlotinib-Adipic-adipate)
top
Crystal data top
C28H33N3O8 | F(000) = 1144 |
Mr = 539.57 | Dx = 1.288 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.2922 (18) Å | Cell parameters from 6695 reflections |
b = 27.500 (3) Å | θ = 2.1–27.5° |
c = 7.0784 (7) Å | µ = 0.10 mm−1 |
β = 90.467 (7)° | T = 150 K |
V = 2781.9 (5) Å3 | Plate, colorless |
Z = 4 | 0.40 × 0.16 × 0.12 mm |
Data collection top
XtaLABmini diffractometer | 5057 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.149 |
Graphite monochromator | θmax = 27.5°, θmin = 1.4° |
Absorption correction: multi-scan SADABS | h = −18→18 |
Tmin = 0.726, Tmax = 1.000 | k = −35→35 |
29176 measured reflections | l = −9→9 |
6367 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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.21 | w = 1/[σ2(Fo2) + (0.0995P)2 + 0.1237P] where P = (Fo2 + 2Fc2)/3 |
6367 reflections | (Δ/σ)max < 0.001 |
364 parameters | Δρmax = 0.34 e Å−3 |
1 restraint | Δρmin = −0.56 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
H1N | 0.340 (2) | 0.8357 (11) | 0.660 (4) | 0.039 (8)* | |
H6A | 0.719 (2) | 0.0498 (11) | 0.275 (4) | 0.064 (10)* | |
O3 | −0.04861 (10) | 0.75280 (6) | 0.4445 (2) | 0.0271 (3) | |
O1 | 0.01645 (11) | 0.83843 (5) | 0.4921 (2) | 0.0264 (3) | |
N3 | 0.24537 (13) | 0.68126 (6) | 0.6438 (3) | 0.0246 (4) | |
N2 | 0.37561 (13) | 0.73013 (6) | 0.7215 (3) | 0.0262 (4) | |
O4 | −0.20501 (12) | 0.70438 (6) | 0.6411 (2) | 0.0357 (4) | |
C12 | 0.22842 (14) | 0.76779 (7) | 0.6218 (3) | 0.0214 (4) | |
O6 | 0.69370 (13) | 0.03167 (6) | 0.3742 (3) | 0.0388 (4) | |
C9 | 0.32543 (15) | 0.77037 (7) | 0.6775 (3) | 0.0226 (4) | |
N1 | 0.36946 (13) | 0.81340 (7) | 0.6904 (3) | 0.0267 (4) | |
C14 | 0.07888 (15) | 0.80221 (7) | 0.5294 (3) | 0.0225 (4) | |
C11 | 0.18968 (14) | 0.72122 (7) | 0.6026 (3) | 0.0216 (4) | |
C13 | 0.17020 (15) | 0.80882 (7) | 0.5850 (3) | 0.0224 (4) | |
H13 | 0.1941 | 0.8401 | 0.5987 | 0.027* | |
O5 | 0.66832 (14) | 0.10153 (6) | 0.5227 (2) | 0.0399 (4) | |
C10 | 0.33293 (16) | 0.68762 (8) | 0.7023 (3) | 0.0258 (4) | |
H10 | 0.3672 | 0.6599 | 0.7324 | 0.031* | |
C15 | 0.04116 (14) | 0.75406 (7) | 0.5049 (3) | 0.0220 (4) | |
O2 | −0.10566 (13) | 0.91124 (7) | 0.6479 (3) | 0.0440 (5) | |
C23 | 0.65674 (16) | 0.05742 (8) | 0.5104 (3) | 0.0283 (5) | |
C20 | −0.09043 (16) | 0.70596 (8) | 0.4001 (3) | 0.0278 (5) | |
H20A | −0.0444 | 0.6858 | 0.3377 | 0.033* | |
H20B | −0.1422 | 0.7108 | 0.3126 | 0.033* | |
C16 | 0.09666 (15) | 0.71421 (8) | 0.5440 (3) | 0.0239 (4) | |
H16 | 0.0726 | 0.6829 | 0.5316 | 0.029* | |
C8 | 0.48783 (15) | 0.86236 (8) | 0.8394 (3) | 0.0269 (5) | |
H8 | 0.4405 | 0.8828 | 0.8814 | 0.032* | |
C7 | 0.46592 (15) | 0.82111 (8) | 0.7329 (3) | 0.0252 (4) | |
C17 | 0.04491 (16) | 0.88742 (8) | 0.5360 (3) | 0.0293 (5) | |
H17A | 0.0956 | 0.8974 | 0.4543 | 0.035* | |
H17B | 0.0663 | 0.8895 | 0.6661 | 0.035* | |
C21 | −0.12547 (16) | 0.67977 (8) | 0.5720 (3) | 0.0298 (5) | |
H21A | −0.1418 | 0.6465 | 0.5396 | 0.036* | |
H21B | −0.0769 | 0.6789 | 0.6686 | 0.036* | |
C5 | 0.62875 (16) | 0.80098 (9) | 0.7144 (4) | 0.0345 (5) | |
H5 | 0.6759 | 0.7802 | 0.6740 | 0.041* | |
C25 | 0.53735 (18) | −0.01035 (9) | 0.5665 (4) | 0.0345 (5) | |
H25A | 0.5756 | −0.0333 | 0.4973 | 0.041* | |
H25B | 0.5069 | −0.0280 | 0.6676 | 0.041* | |
C6 | 0.53610 (16) | 0.79066 (8) | 0.6674 (3) | 0.0303 (5) | |
H6 | 0.5214 | 0.7638 | 0.5932 | 0.036* | |
C24 | 0.60091 (18) | 0.02895 (9) | 0.6527 (4) | 0.0370 (5) | |
H24A | 0.5625 | 0.0514 | 0.7238 | 0.044* | |
H24B | 0.6440 | 0.0136 | 0.7409 | 0.044* | |
C4 | 0.65180 (16) | 0.84140 (9) | 0.8198 (3) | 0.0348 (5) | |
H4 | 0.7141 | 0.8478 | 0.8491 | 0.042* | |
C3 | 0.58209 (16) | 0.87282 (9) | 0.8829 (3) | 0.0305 (5) | |
C18 | −0.03862 (18) | 0.91962 (8) | 0.5056 (4) | 0.0334 (5) | |
H18A | −0.0193 | 0.9534 | 0.5084 | 0.040* | |
H18B | −0.0662 | 0.9130 | 0.3826 | 0.040* | |
C2 | 0.60571 (18) | 0.91514 (9) | 0.9928 (4) | 0.0371 (6) | |
C1 | 0.6274 (2) | 0.94928 (11) | 1.0843 (4) | 0.0478 (7) | |
H1 | 0.6446 | 0.9762 | 1.1563 | 0.057* | |
C22 | −0.2441 (2) | 0.67984 (12) | 0.8000 (4) | 0.0530 (8) | |
H22A | −0.2979 | 0.6974 | 0.8433 | 0.080* | |
H22B | −0.1983 | 0.6781 | 0.8996 | 0.080* | |
H22C | −0.2624 | 0.6476 | 0.7636 | 0.080* | |
C19 | −0.1864 (2) | 0.94060 (11) | 0.6226 (5) | 0.0585 (8) | |
H19A | −0.2302 | 0.9339 | 0.7215 | 0.088* | |
H19B | −0.2148 | 0.9334 | 0.5024 | 0.088* | |
H19C | −0.1689 | 0.9743 | 0.6268 | 0.088* | |
O7 | 0.84952 (13) | 0.09803 (6) | −0.1179 (2) | 0.0373 (4) | |
O8 | 0.75517 (13) | 0.08462 (6) | 0.1214 (3) | 0.0398 (4) | |
C26 | 0.82373 (15) | 0.07292 (8) | 0.0187 (3) | 0.0264 (4) | |
C27 | 0.87779 (16) | 0.02642 (8) | 0.0659 (3) | 0.0298 (5) | |
H27A | 0.8861 | 0.0244 | 0.2018 | 0.036* | |
H27B | 0.8406 | −0.0013 | 0.0265 | 0.036* | |
C28 | 0.97366 (16) | 0.02302 (8) | −0.0269 (3) | 0.0311 (5) | |
H28A | 0.9656 | 0.0240 | −0.1630 | 0.037* | |
H28B | 1.0108 | 0.0510 | 0.0101 | 0.037* | |
H3 | 0.217 (3) | 0.6500 (13) | 0.635 (5) | 0.061 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0215 (7) | 0.0270 (8) | 0.0326 (8) | −0.0054 (6) | −0.0053 (6) | 0.0004 (6) |
O1 | 0.0246 (8) | 0.0198 (7) | 0.0348 (8) | −0.0009 (6) | −0.0058 (6) | 0.0018 (6) |
N3 | 0.0240 (9) | 0.0187 (8) | 0.0312 (9) | −0.0011 (7) | 0.0019 (7) | 0.0004 (7) |
N2 | 0.0241 (9) | 0.0223 (9) | 0.0321 (9) | −0.0020 (7) | −0.0009 (7) | 0.0033 (7) |
O4 | 0.0293 (9) | 0.0400 (10) | 0.0379 (9) | −0.0026 (7) | 0.0033 (7) | 0.0016 (7) |
C12 | 0.0216 (10) | 0.0199 (9) | 0.0227 (9) | −0.0027 (7) | −0.0002 (7) | 0.0001 (7) |
O6 | 0.0439 (10) | 0.0221 (8) | 0.0505 (10) | −0.0039 (7) | 0.0162 (8) | −0.0049 (7) |
C9 | 0.0226 (10) | 0.0224 (10) | 0.0226 (9) | −0.0027 (8) | −0.0018 (8) | 0.0009 (8) |
N1 | 0.0203 (9) | 0.0207 (9) | 0.0390 (10) | −0.0023 (7) | −0.0070 (8) | 0.0012 (8) |
C14 | 0.0245 (10) | 0.0209 (10) | 0.0220 (9) | −0.0008 (8) | −0.0007 (8) | 0.0014 (7) |
C11 | 0.0230 (10) | 0.0203 (9) | 0.0216 (9) | −0.0017 (8) | 0.0017 (8) | −0.0003 (7) |
C13 | 0.0231 (10) | 0.0200 (9) | 0.0241 (9) | −0.0040 (8) | −0.0018 (8) | 0.0007 (8) |
O5 | 0.0549 (12) | 0.0212 (8) | 0.0437 (9) | −0.0023 (7) | 0.0042 (8) | −0.0038 (7) |
C10 | 0.0249 (11) | 0.0210 (10) | 0.0316 (10) | 0.0005 (8) | 0.0009 (8) | 0.0027 (8) |
C15 | 0.0207 (10) | 0.0239 (10) | 0.0214 (9) | −0.0032 (8) | −0.0009 (7) | −0.0008 (8) |
O2 | 0.0389 (10) | 0.0393 (10) | 0.0539 (11) | 0.0105 (8) | 0.0114 (8) | 0.0076 (8) |
C23 | 0.0246 (11) | 0.0234 (11) | 0.0367 (11) | −0.0009 (8) | −0.0048 (9) | −0.0010 (9) |
C20 | 0.0261 (11) | 0.0285 (11) | 0.0288 (10) | −0.0078 (9) | −0.0050 (9) | −0.0031 (9) |
C16 | 0.0243 (10) | 0.0216 (10) | 0.0259 (9) | −0.0052 (8) | 0.0003 (8) | −0.0021 (8) |
C8 | 0.0230 (11) | 0.0248 (10) | 0.0329 (11) | −0.0011 (8) | −0.0042 (8) | −0.0005 (9) |
C7 | 0.0202 (10) | 0.0241 (10) | 0.0313 (10) | −0.0037 (8) | −0.0051 (8) | 0.0012 (8) |
C17 | 0.0320 (12) | 0.0201 (10) | 0.0357 (11) | −0.0028 (9) | −0.0020 (9) | 0.0011 (9) |
C21 | 0.0263 (11) | 0.0287 (11) | 0.0343 (11) | −0.0051 (9) | −0.0043 (9) | −0.0004 (9) |
C5 | 0.0237 (11) | 0.0328 (12) | 0.0471 (13) | 0.0021 (9) | 0.0013 (10) | −0.0005 (10) |
C25 | 0.0340 (12) | 0.0268 (11) | 0.0427 (12) | −0.0059 (9) | 0.0018 (10) | 0.0064 (10) |
C6 | 0.0265 (11) | 0.0262 (11) | 0.0381 (12) | −0.0029 (9) | −0.0002 (9) | −0.0037 (9) |
C24 | 0.0346 (13) | 0.0363 (13) | 0.0400 (13) | −0.0067 (10) | 0.0020 (10) | −0.0010 (10) |
C4 | 0.0200 (11) | 0.0401 (13) | 0.0441 (13) | −0.0022 (10) | −0.0074 (9) | 0.0021 (11) |
C3 | 0.0269 (11) | 0.0332 (12) | 0.0314 (11) | −0.0067 (9) | −0.0068 (9) | 0.0003 (9) |
C18 | 0.0350 (13) | 0.0253 (11) | 0.0399 (12) | 0.0041 (9) | −0.0013 (10) | 0.0040 (9) |
C2 | 0.0285 (12) | 0.0416 (14) | 0.0411 (13) | −0.0091 (10) | −0.0041 (10) | −0.0043 (11) |
C1 | 0.0429 (16) | 0.0490 (16) | 0.0513 (15) | −0.0164 (13) | −0.0001 (12) | −0.0153 (13) |
C22 | 0.0469 (17) | 0.068 (2) | 0.0440 (15) | −0.0087 (15) | 0.0127 (13) | 0.0090 (14) |
C19 | 0.0398 (16) | 0.0465 (17) | 0.089 (2) | 0.0138 (13) | 0.0047 (16) | −0.0029 (16) |
O7 | 0.0425 (10) | 0.0277 (8) | 0.0419 (9) | 0.0129 (7) | 0.0115 (8) | 0.0108 (7) |
O8 | 0.0335 (10) | 0.0321 (9) | 0.0540 (11) | 0.0115 (7) | 0.0155 (8) | 0.0092 (8) |
C26 | 0.0234 (10) | 0.0218 (10) | 0.0339 (11) | 0.0032 (8) | −0.0005 (9) | −0.0009 (8) |
C27 | 0.0303 (12) | 0.0214 (10) | 0.0379 (11) | 0.0056 (9) | 0.0049 (9) | 0.0055 (9) |
C28 | 0.0273 (11) | 0.0242 (11) | 0.0420 (12) | 0.0057 (9) | 0.0054 (10) | 0.0070 (9) |
Geometric parameters (Å, º) top
O3—C15 | 1.350 (2) | C17—C18 | 1.500 (3) |
O3—C20 | 1.453 (2) | C17—H17A | 0.9700 |
O1—C14 | 1.362 (3) | C17—H17B | 0.9700 |
O1—C17 | 1.440 (2) | C21—H21A | 0.9700 |
N3—C10 | 1.327 (3) | C21—H21B | 0.9700 |
N3—C11 | 1.386 (3) | C5—C4 | 1.377 (3) |
N3—H3 | 0.95 (4) | C5—C6 | 1.392 (3) |
N2—C10 | 1.325 (3) | C5—H5 | 0.9300 |
N2—C9 | 1.354 (3) | C25—C25i | 1.528 (5) |
O4—C21 | 1.414 (3) | C25—C24 | 1.535 (3) |
O4—C22 | 1.429 (3) | C25—H25A | 0.9700 |
C12—C11 | 1.401 (3) | C25—H25B | 0.9700 |
C12—C13 | 1.425 (3) | C6—H6 | 0.9300 |
C12—C9 | 1.440 (3) | C24—H24A | 0.9700 |
O6—C23 | 1.311 (3) | C24—H24B | 0.9700 |
O6—H6A | 0.937 (18) | C4—C3 | 1.395 (4) |
C9—N1 | 1.343 (3) | C4—H4 | 0.9300 |
N1—C7 | 1.425 (3) | C3—C2 | 1.439 (3) |
N1—H1N | 0.78 (3) | C18—H18A | 0.9700 |
C14—C13 | 1.372 (3) | C18—H18B | 0.9700 |
C14—C15 | 1.439 (3) | C2—C1 | 1.180 (4) |
C11—C16 | 1.403 (3) | C1—H1 | 0.9300 |
C13—H13 | 0.9300 | C22—H22A | 0.9600 |
O5—C23 | 1.227 (3) | C22—H22B | 0.9600 |
C10—H10 | 0.9300 | C22—H22C | 0.9600 |
C15—C16 | 1.380 (3) | C19—H19A | 0.9600 |
O2—C18 | 1.415 (3) | C19—H19B | 0.9600 |
O2—C19 | 1.419 (3) | C19—H19C | 0.9600 |
C23—C24 | 1.509 (3) | O7—C26 | 1.246 (3) |
C20—C21 | 1.504 (3) | O8—C26 | 1.266 (3) |
C20—H20A | 0.9700 | C26—C27 | 1.529 (3) |
C20—H20B | 0.9700 | C27—C28 | 1.527 (3) |
C16—H16 | 0.9300 | C27—H27A | 0.9700 |
C8—C7 | 1.396 (3) | C27—H27B | 0.9700 |
C8—C3 | 1.409 (3) | C28—C28ii | 1.520 (4) |
C8—H8 | 0.9300 | C28—H28A | 0.9700 |
C7—C6 | 1.389 (3) | C28—H28B | 0.9700 |
| | | |
C15—O3—C20 | 118.67 (17) | C20—C21—H21B | 109.9 |
C14—O1—C17 | 117.33 (17) | H21A—C21—H21B | 108.3 |
C10—N3—C11 | 119.99 (18) | C4—C5—C6 | 121.1 (2) |
C10—N3—H3 | 123 (2) | C4—C5—H5 | 119.4 |
C11—N3—H3 | 117 (2) | C6—C5—H5 | 119.4 |
C10—N2—C9 | 117.05 (18) | C25i—C25—C24 | 113.0 (2) |
C21—O4—C22 | 111.5 (2) | C25i—C25—H25A | 109.0 |
C11—C12—C13 | 118.45 (19) | C24—C25—H25A | 109.0 |
C11—C12—C9 | 116.76 (18) | C25i—C25—H25B | 109.0 |
C13—C12—C9 | 124.79 (18) | C24—C25—H25B | 109.0 |
C23—O6—H6A | 115 (2) | H25A—C25—H25B | 107.8 |
N1—C9—N2 | 117.22 (19) | C7—C6—C5 | 119.0 (2) |
N1—C9—C12 | 120.77 (18) | C7—C6—H6 | 120.5 |
N2—C9—C12 | 122.00 (18) | C5—C6—H6 | 120.5 |
C9—N1—C7 | 126.70 (19) | C23—C24—C25 | 114.5 (2) |
C9—N1—H1N | 115 (2) | C23—C24—H24A | 108.6 |
C7—N1—H1N | 118 (2) | C25—C24—H24A | 108.6 |
O1—C14—C13 | 125.36 (19) | C23—C24—H24B | 108.6 |
O1—C14—C15 | 113.92 (18) | C25—C24—H24B | 108.6 |
C13—C14—C15 | 120.71 (18) | H24A—C24—H24B | 107.6 |
N3—C11—C12 | 118.57 (18) | C5—C4—C3 | 120.3 (2) |
N3—C11—C16 | 119.62 (18) | C5—C4—H4 | 119.8 |
C12—C11—C16 | 121.81 (19) | C3—C4—H4 | 119.8 |
C14—C13—C12 | 120.01 (18) | C4—C3—C8 | 119.2 (2) |
C14—C13—H13 | 120.0 | C4—C3—C2 | 120.6 (2) |
C12—C13—H13 | 120.0 | C8—C3—C2 | 120.2 (2) |
N2—C10—N3 | 125.5 (2) | O2—C18—C17 | 110.14 (19) |
N2—C10—H10 | 117.3 | O2—C18—H18A | 109.6 |
N3—C10—H10 | 117.3 | C17—C18—H18A | 109.6 |
O3—C15—C16 | 125.92 (18) | O2—C18—H18B | 109.6 |
O3—C15—C14 | 114.58 (18) | C17—C18—H18B | 109.6 |
C16—C15—C14 | 119.51 (18) | H18A—C18—H18B | 108.1 |
C18—O2—C19 | 111.9 (2) | C1—C2—C3 | 178.1 (3) |
O5—C23—O6 | 122.1 (2) | C2—C1—H1 | 180.0 |
O5—C23—C24 | 122.5 (2) | O4—C22—H22A | 109.5 |
O6—C23—C24 | 115.4 (2) | O4—C22—H22B | 109.5 |
O3—C20—C21 | 112.85 (17) | H22A—C22—H22B | 109.5 |
O3—C20—H20A | 109.0 | O4—C22—H22C | 109.5 |
C21—C20—H20A | 109.0 | H22A—C22—H22C | 109.5 |
O3—C20—H20B | 109.0 | H22B—C22—H22C | 109.5 |
C21—C20—H20B | 109.0 | O2—C19—H19A | 109.5 |
H20A—C20—H20B | 107.8 | O2—C19—H19B | 109.5 |
C15—C16—C11 | 119.47 (19) | H19A—C19—H19B | 109.5 |
C15—C16—H16 | 120.3 | O2—C19—H19C | 109.5 |
C11—C16—H16 | 120.3 | H19A—C19—H19C | 109.5 |
C7—C8—C3 | 119.6 (2) | H19B—C19—H19C | 109.5 |
C7—C8—H8 | 120.2 | O7—C26—O8 | 122.7 (2) |
C3—C8—H8 | 120.2 | O7—C26—C27 | 118.71 (19) |
C6—C7—C8 | 120.7 (2) | O8—C26—C27 | 118.63 (19) |
C6—C7—N1 | 122.67 (19) | C28—C27—C26 | 114.27 (18) |
C8—C7—N1 | 116.58 (19) | C28—C27—H27A | 108.7 |
O1—C17—C18 | 107.35 (18) | C26—C27—H27A | 108.7 |
O1—C17—H17A | 110.2 | C28—C27—H27B | 108.7 |
C18—C17—H17A | 110.2 | C26—C27—H27B | 108.7 |
O1—C17—H17B | 110.2 | H27A—C27—H27B | 107.6 |
C18—C17—H17B | 110.2 | C28ii—C28—C27 | 112.8 (2) |
H17A—C17—H17B | 108.5 | C28ii—C28—H28A | 109.0 |
O4—C21—C20 | 108.93 (19) | C27—C28—H28A | 109.0 |
O4—C21—H21A | 109.9 | C28ii—C28—H28B | 109.0 |
C20—C21—H21A | 109.9 | C27—C28—H28B | 109.0 |
O4—C21—H21B | 109.9 | H28A—C28—H28B | 107.8 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y, −z. |
(Erlotinib-glutaric-hydrate)
top
Crystal data top
C27H33N3O9 | Z = 2 |
Mr = 543.56 | F(000) = 576 |
Triclinic, P1 | Dx = 1.310 Mg m−3 |
a = 7.916 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.012 (15) Å | Cell parameters from 3232 reflections |
c = 14.349 (14) Å | θ = 1.7–27.5° |
α = 61.73 (3)° | µ = 0.10 mm−1 |
β = 79.64 (6)° | T = 150 K |
γ = 86.58 (6)° | Plate, colorless |
V = 1378 (3) Å3 | 0.30 × 0.20 × 0.16 mm |
Data collection top
XtaLABmini diffractometer | 4171 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.076 |
Graphite monochromator | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan SADABS | h = −10→10 |
Tmin = 0.626, Tmax = 1.000 | k = −18→17 |
14359 measured reflections | l = −18→18 |
6237 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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.197 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0735P)2] where P = (Fo2 + 2Fc2)/3 |
6237 reflections | (Δ/σ)max < 0.001 |
372 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
O9 | 0.6897 (3) | 0.55637 (18) | 0.7932 (2) | 0.0439 (5) | |
H1 | 0.818 (4) | −0.063 (2) | 1.123 (2) | 0.037 (8)* | |
H9B | 0.676 (5) | 0.532 (3) | 0.755 (3) | 0.065 (13)* | |
H5A | −0.208 (6) | 0.677 (4) | 0.741 (4) | 0.108 (16)* | |
H7 | 0.569 (6) | 1.023 (4) | 0.704 (4) | 0.122 (18)* | |
H9A | 0.731 (6) | 0.512 (4) | 0.855 (4) | 0.105 (17)* | |
O3 | 0.6315 (2) | 0.29470 (13) | 0.96416 (13) | 0.0283 (4) | |
O1 | 0.5331 (2) | 0.35140 (13) | 0.78200 (13) | 0.0280 (4) | |
N3 | 0.6549 (3) | −0.00483 (16) | 0.81022 (16) | 0.0276 (5) | |
N1 | 0.8333 (3) | −0.10565 (17) | 1.09636 (17) | 0.0260 (5) | |
O8 | 0.2608 (2) | 1.00671 (15) | 0.74993 (14) | 0.0370 (5) | |
O2 | 0.6014 (2) | 0.56656 (14) | 0.60101 (16) | 0.0385 (5) | |
C15 | 0.5867 (3) | 0.24694 (19) | 0.83196 (18) | 0.0239 (5) | |
N2 | 0.7825 (3) | −0.13877 (17) | 0.95800 (16) | 0.0286 (5) | |
C12 | 0.7129 (3) | 0.03773 (19) | 0.94816 (18) | 0.0232 (5) | |
C9 | 0.7768 (3) | −0.07130 (19) | 1.00088 (19) | 0.0235 (5) | |
C11 | 0.6531 (3) | 0.06786 (19) | 0.85080 (18) | 0.0232 (5) | |
C13 | 0.7060 (3) | 0.11384 (19) | 0.98769 (18) | 0.0241 (5) | |
H13 | 0.7433 | 0.0943 | 1.0521 | 0.029* | |
O5 | −0.1874 (3) | 0.75208 (18) | 0.72299 (19) | 0.0486 (6) | |
C14 | 0.6447 (3) | 0.21615 (19) | 0.93213 (18) | 0.0235 (5) | |
O4 | 0.7701 (3) | 0.45364 (16) | 1.00005 (16) | 0.0442 (5) | |
O7 | 0.5184 (2) | 1.02943 (17) | 0.64482 (15) | 0.0397 (5) | |
C10 | 0.7184 (3) | −0.1015 (2) | 0.8653 (2) | 0.0289 (6) | |
H10 | 0.7192 | −0.1494 | 0.8374 | 0.035* | |
C7 | 0.8964 (3) | −0.20770 (19) | 1.16541 (19) | 0.0249 (5) | |
C16 | 0.5902 (3) | 0.17279 (19) | 0.79367 (18) | 0.0250 (5) | |
H16 | 0.5510 | 0.1921 | 0.7299 | 0.030* | |
C17 | 0.4837 (3) | 0.3873 (2) | 0.67766 (18) | 0.0267 (5) | |
H17A | 0.3836 | 0.3459 | 0.6852 | 0.032* | |
H17B | 0.5768 | 0.3772 | 0.6293 | 0.032* | |
O6 | 0.0817 (3) | 0.69073 (16) | 0.72288 (16) | 0.0447 (5) | |
C27 | 0.3497 (3) | 1.02208 (19) | 0.6640 (2) | 0.0296 (6) | |
C23 | −0.0179 (4) | 0.7640 (2) | 0.7093 (2) | 0.0349 (6) | |
C6 | 0.9106 (3) | −0.2995 (2) | 1.1493 (2) | 0.0291 (5) | |
H6 | 0.8779 | −0.2968 | 1.0891 | 0.035* | |
C8 | 0.9480 (3) | −0.21326 (19) | 1.25665 (19) | 0.0260 (5) | |
H8 | 0.9401 | −0.1524 | 1.2671 | 0.031* | |
C4 | 1.0249 (3) | −0.4013 (2) | 1.3158 (2) | 0.0313 (6) | |
H4 | 1.0671 | −0.4653 | 1.3651 | 0.038* | |
C2 | 1.0618 (3) | −0.3120 (2) | 1.4254 (2) | 0.0332 (6) | |
C20 | 0.6964 (3) | 0.2677 (2) | 1.0623 (2) | 0.0312 (6) | |
H20A | 0.8179 | 0.2528 | 1.0536 | 0.037* | |
H20B | 0.6360 | 0.2037 | 1.1217 | 0.037* | |
C21 | 0.6686 (4) | 0.3626 (2) | 1.0848 (2) | 0.0356 (6) | |
H21A | 0.5481 | 0.3803 | 1.0889 | 0.043* | |
H21B | 0.7019 | 0.3444 | 1.1530 | 0.043* | |
C3 | 1.0112 (3) | −0.3095 (2) | 1.33222 (19) | 0.0283 (5) | |
C5 | 0.9747 (3) | −0.3953 (2) | 1.2249 (2) | 0.0325 (6) | |
H5 | 0.9839 | −0.4559 | 1.2141 | 0.039* | |
C18 | 0.4434 (3) | 0.5060 (2) | 0.6339 (2) | 0.0306 (6) | |
H18A | 0.3846 | 0.5291 | 0.5732 | 0.037* | |
H18B | 0.3693 | 0.5179 | 0.6888 | 0.037* | |
C24 | 0.0385 (4) | 0.8795 (2) | 0.6756 (2) | 0.0396 (7) | |
H24A | −0.0513 | 0.9282 | 0.6442 | 0.048* | |
H24B | 0.0524 | 0.8844 | 0.7390 | 0.048* | |
C25 | 0.2054 (4) | 0.9167 (2) | 0.5954 (2) | 0.0380 (6) | |
H25A | 0.1880 | 0.9192 | 0.5290 | 0.046* | |
H25B | 0.2924 | 0.8640 | 0.6236 | 0.046* | |
C1 | 1.1019 (4) | −0.3133 (2) | 1.5021 (2) | 0.0454 (7) | |
H1A | 1.1333 | −0.3143 | 1.5620 | 0.054* | |
C26 | 0.2715 (4) | 1.0300 (2) | 0.5705 (2) | 0.0354 (6) | |
H26A | 0.3575 | 1.0586 | 0.5057 | 0.043* | |
H26B | 0.1771 | 1.0794 | 0.5583 | 0.043* | |
C19 | 0.5762 (4) | 0.6811 (2) | 0.5565 (3) | 0.0504 (8) | |
H19A | 0.6854 | 0.7184 | 0.5356 | 0.076* | |
H19B | 0.5048 | 0.6961 | 0.6093 | 0.076* | |
H19C | 0.5217 | 0.7055 | 0.4947 | 0.076* | |
C22 | 0.7798 (5) | 0.5397 (3) | 1.0267 (3) | 0.0538 (9) | |
H22A | 0.8489 | 0.5989 | 0.9681 | 0.081* | |
H22B | 0.8307 | 0.5137 | 1.0900 | 0.081* | |
H22C | 0.6663 | 0.5640 | 1.0397 | 0.081* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O9 | 0.0522 (13) | 0.0381 (12) | 0.0477 (14) | 0.0025 (10) | −0.0159 (11) | −0.0230 (11) |
O3 | 0.0393 (10) | 0.0264 (9) | 0.0239 (9) | 0.0077 (8) | −0.0144 (8) | −0.0132 (7) |
O1 | 0.0370 (9) | 0.0240 (9) | 0.0230 (9) | 0.0068 (7) | −0.0141 (7) | −0.0086 (7) |
N3 | 0.0298 (11) | 0.0294 (11) | 0.0241 (11) | −0.0003 (9) | −0.0054 (9) | −0.0127 (9) |
N1 | 0.0331 (11) | 0.0203 (10) | 0.0250 (11) | 0.0051 (9) | −0.0108 (9) | −0.0095 (9) |
O8 | 0.0433 (11) | 0.0422 (11) | 0.0276 (10) | 0.0081 (9) | −0.0072 (9) | −0.0185 (9) |
O2 | 0.0391 (10) | 0.0240 (9) | 0.0440 (12) | 0.0031 (8) | −0.0126 (9) | −0.0077 (8) |
C15 | 0.0238 (11) | 0.0237 (12) | 0.0206 (12) | 0.0005 (10) | −0.0054 (9) | −0.0071 (10) |
N2 | 0.0319 (11) | 0.0283 (11) | 0.0268 (11) | 0.0035 (9) | −0.0082 (9) | −0.0131 (9) |
C12 | 0.0226 (11) | 0.0256 (12) | 0.0180 (11) | −0.0023 (10) | −0.0027 (9) | −0.0076 (10) |
C9 | 0.0215 (11) | 0.0243 (12) | 0.0224 (12) | −0.0012 (9) | −0.0026 (9) | −0.0093 (10) |
C11 | 0.0226 (11) | 0.0261 (12) | 0.0208 (12) | −0.0016 (10) | −0.0024 (9) | −0.0111 (10) |
C13 | 0.0254 (11) | 0.0262 (12) | 0.0198 (12) | −0.0001 (10) | −0.0060 (10) | −0.0093 (10) |
O5 | 0.0437 (12) | 0.0396 (12) | 0.0697 (16) | 0.0007 (10) | −0.0108 (11) | −0.0312 (11) |
C14 | 0.0251 (11) | 0.0235 (12) | 0.0215 (12) | 0.0016 (10) | −0.0053 (10) | −0.0100 (10) |
O4 | 0.0624 (13) | 0.0339 (10) | 0.0464 (12) | 0.0002 (10) | −0.0165 (10) | −0.0246 (10) |
O7 | 0.0385 (11) | 0.0549 (13) | 0.0279 (10) | −0.0011 (9) | −0.0081 (9) | −0.0201 (9) |
C10 | 0.0328 (13) | 0.0299 (13) | 0.0286 (13) | 0.0009 (11) | −0.0060 (11) | −0.0173 (11) |
C7 | 0.0226 (11) | 0.0241 (12) | 0.0239 (12) | 0.0005 (10) | −0.0043 (10) | −0.0078 (10) |
C16 | 0.0249 (11) | 0.0285 (12) | 0.0191 (12) | −0.0016 (10) | −0.0057 (10) | −0.0084 (10) |
C17 | 0.0313 (12) | 0.0279 (12) | 0.0184 (12) | 0.0031 (10) | −0.0099 (10) | −0.0073 (10) |
O6 | 0.0519 (12) | 0.0393 (11) | 0.0443 (12) | 0.0092 (10) | −0.0197 (10) | −0.0178 (10) |
C27 | 0.0398 (14) | 0.0197 (12) | 0.0277 (14) | 0.0047 (11) | −0.0116 (12) | −0.0083 (10) |
C23 | 0.0452 (16) | 0.0368 (15) | 0.0275 (14) | 0.0019 (13) | −0.0095 (12) | −0.0179 (12) |
C6 | 0.0293 (12) | 0.0275 (13) | 0.0291 (13) | 0.0016 (11) | −0.0079 (11) | −0.0112 (11) |
C8 | 0.0255 (12) | 0.0239 (12) | 0.0276 (13) | 0.0023 (10) | −0.0066 (10) | −0.0109 (10) |
C4 | 0.0314 (13) | 0.0215 (12) | 0.0350 (14) | 0.0052 (10) | −0.0096 (11) | −0.0075 (11) |
C2 | 0.0363 (14) | 0.0285 (13) | 0.0344 (15) | 0.0093 (11) | −0.0129 (12) | −0.0132 (12) |
C20 | 0.0415 (14) | 0.0316 (13) | 0.0242 (13) | 0.0060 (12) | −0.0165 (11) | −0.0131 (11) |
C21 | 0.0454 (15) | 0.0366 (14) | 0.0325 (15) | 0.0102 (13) | −0.0161 (12) | −0.0205 (12) |
C3 | 0.0256 (12) | 0.0289 (13) | 0.0236 (13) | 0.0039 (10) | −0.0053 (10) | −0.0069 (10) |
C5 | 0.0350 (13) | 0.0244 (12) | 0.0392 (15) | 0.0045 (11) | −0.0089 (12) | −0.0155 (12) |
C18 | 0.0356 (13) | 0.0280 (13) | 0.0252 (13) | 0.0057 (11) | −0.0121 (11) | −0.0084 (11) |
C24 | 0.0459 (16) | 0.0362 (15) | 0.0391 (16) | −0.0006 (13) | −0.0069 (13) | −0.0197 (13) |
C25 | 0.0459 (16) | 0.0417 (16) | 0.0304 (15) | −0.0003 (13) | −0.0080 (12) | −0.0196 (13) |
C1 | 0.0569 (18) | 0.0459 (17) | 0.0387 (17) | 0.0214 (15) | −0.0234 (15) | −0.0214 (14) |
C26 | 0.0422 (15) | 0.0375 (15) | 0.0249 (14) | 0.0014 (12) | −0.0111 (12) | −0.0115 (12) |
C19 | 0.063 (2) | 0.0243 (14) | 0.055 (2) | 0.0015 (14) | −0.0204 (17) | −0.0081 (13) |
C22 | 0.070 (2) | 0.0415 (17) | 0.073 (2) | 0.0121 (16) | −0.0379 (19) | −0.0388 (17) |
Geometric parameters (Å, º) top
O9—H9B | 0.80 (4) | C17—H17B | 0.9700 |
O9—H9A | 0.91 (5) | O6—C23 | 1.217 (3) |
O3—C14 | 1.372 (3) | C27—C26 | 1.531 (4) |
O3—C20 | 1.456 (3) | C23—C24 | 1.524 (4) |
O1—C15 | 1.370 (3) | C6—C5 | 1.405 (4) |
O1—C17 | 1.456 (3) | C6—H6 | 0.9300 |
N3—C10 | 1.327 (3) | C8—C3 | 1.405 (3) |
N3—C11 | 1.391 (3) | C8—H8 | 0.9300 |
N1—C9 | 1.371 (3) | C4—C5 | 1.395 (4) |
N1—C7 | 1.423 (3) | C4—C3 | 1.407 (4) |
N1—H1 | 0.83 (3) | C4—H4 | 0.9300 |
O8—C27 | 1.231 (3) | C2—C1 | 1.192 (4) |
O2—C18 | 1.429 (4) | C2—C3 | 1.448 (4) |
O2—C19 | 1.435 (4) | C20—C21 | 1.505 (4) |
C15—C16 | 1.383 (4) | C20—H20A | 0.9700 |
C15—C14 | 1.446 (3) | C20—H20B | 0.9700 |
N2—C9 | 1.345 (3) | C21—H21A | 0.9700 |
N2—C10 | 1.361 (3) | C21—H21B | 0.9700 |
C12—C13 | 1.420 (3) | C5—H5 | 0.9300 |
C12—C11 | 1.417 (3) | C18—H18A | 0.9700 |
C12—C9 | 1.453 (4) | C18—H18B | 0.9700 |
C11—C16 | 1.414 (4) | C24—C25 | 1.519 (4) |
C13—C14 | 1.378 (3) | C24—H24A | 0.9700 |
C13—H13 | 0.9300 | C24—H24B | 0.9700 |
O5—C23 | 1.329 (4) | C25—C26 | 1.555 (4) |
O5—H5A | 0.97 (5) | C25—H25A | 0.9700 |
O4—C21 | 1.433 (4) | C25—H25B | 0.9700 |
O4—C22 | 1.437 (4) | C1—H1A | 0.9300 |
O7—C27 | 1.314 (4) | C26—H26A | 0.9700 |
O7—H7 | 0.97 (5) | C26—H26B | 0.9700 |
C10—H10 | 0.9300 | C19—H19A | 0.9600 |
C7—C8 | 1.406 (4) | C19—H19B | 0.9600 |
C7—C6 | 1.405 (4) | C19—H19C | 0.9600 |
C16—H16 | 0.9300 | C22—H22A | 0.9600 |
C17—C18 | 1.510 (4) | C22—H22B | 0.9600 |
C17—H17A | 0.9700 | C22—H22C | 0.9600 |
| | | |
H9B—O9—H9A | 119 (4) | C5—C4—H4 | 120.3 |
C14—O3—C20 | 116.17 (19) | C3—C4—H4 | 120.3 |
C15—O1—C17 | 116.32 (18) | C1—C2—C3 | 179.3 (3) |
C10—N3—C11 | 117.0 (2) | O3—C20—C21 | 108.3 (2) |
C9—N1—C7 | 130.4 (2) | O3—C20—H20A | 110.0 |
C9—N1—H1 | 116 (2) | C21—C20—H20A | 110.0 |
C7—N1—H1 | 113 (2) | O3—C20—H20B | 110.0 |
C18—O2—C19 | 112.4 (2) | C21—C20—H20B | 110.0 |
O1—C15—C16 | 125.5 (2) | H20A—C20—H20B | 108.4 |
O1—C15—C14 | 114.8 (2) | O4—C21—C20 | 108.9 (2) |
C16—C15—C14 | 119.7 (2) | O4—C21—H21A | 109.9 |
C9—N2—C10 | 116.6 (2) | C20—C21—H21A | 109.9 |
C13—C12—C11 | 119.0 (2) | O4—C21—H21B | 109.9 |
C13—C12—C9 | 124.7 (2) | C20—C21—H21B | 109.9 |
C11—C12—C9 | 116.4 (2) | H21A—C21—H21B | 108.3 |
N2—C9—N1 | 119.4 (2) | C8—C3—C4 | 119.6 (2) |
N2—C9—C12 | 121.6 (2) | C8—C3—C2 | 119.1 (2) |
N1—C9—C12 | 119.0 (2) | C4—C3—C2 | 121.3 (2) |
N3—C11—C16 | 119.1 (2) | C4—C5—C6 | 121.3 (2) |
N3—C11—C12 | 120.8 (2) | C4—C5—H5 | 119.3 |
C16—C11—C12 | 120.1 (2) | C6—C5—H5 | 119.3 |
C14—C13—C12 | 121.0 (2) | O2—C18—C17 | 108.3 (2) |
C14—C13—H13 | 119.5 | O2—C18—H18A | 110.0 |
C12—C13—H13 | 119.5 | C17—C18—H18A | 110.0 |
C23—O5—H5A | 105 (3) | O2—C18—H18B | 110.0 |
O3—C14—C13 | 125.3 (2) | C17—C18—H18B | 110.0 |
O3—C14—C15 | 115.0 (2) | H18A—C18—H18B | 108.4 |
C13—C14—C15 | 119.7 (2) | C25—C24—C23 | 113.5 (2) |
C21—O4—C22 | 112.1 (2) | C25—C24—H24A | 108.9 |
C27—O7—H7 | 115 (3) | C23—C24—H24A | 108.9 |
N3—C10—N2 | 127.5 (2) | C25—C24—H24B | 108.9 |
N3—C10—H10 | 116.2 | C23—C24—H24B | 108.9 |
N2—C10—H10 | 116.2 | H24A—C24—H24B | 107.7 |
C8—C7—C6 | 119.3 (2) | C24—C25—C26 | 113.0 (2) |
C8—C7—N1 | 114.9 (2) | C24—C25—H25A | 109.0 |
C6—C7—N1 | 125.8 (2) | C26—C25—H25A | 109.0 |
C15—C16—C11 | 120.5 (2) | C24—C25—H25B | 109.0 |
C15—C16—H16 | 119.8 | C26—C25—H25B | 109.0 |
C11—C16—H16 | 119.8 | H25A—C25—H25B | 107.8 |
O1—C17—C18 | 107.3 (2) | C2—C1—H1A | 180.0 |
O1—C17—H17A | 110.3 | C27—C26—C25 | 110.7 (2) |
C18—C17—H17A | 110.3 | C27—C26—H26A | 109.5 |
O1—C17—H17B | 110.3 | C25—C26—H26A | 109.5 |
C18—C17—H17B | 110.3 | C27—C26—H26B | 109.5 |
H17A—C17—H17B | 108.5 | C25—C26—H26B | 109.5 |
O8—C27—O7 | 123.9 (2) | H26A—C26—H26B | 108.1 |
O8—C27—C26 | 122.2 (2) | O2—C19—H19A | 109.5 |
O7—C27—C26 | 113.8 (2) | O2—C19—H19B | 109.5 |
O6—C23—O5 | 123.9 (3) | H19A—C19—H19B | 109.5 |
O6—C23—C24 | 123.5 (3) | O2—C19—H19C | 109.5 |
O5—C23—C24 | 112.6 (2) | H19A—C19—H19C | 109.5 |
C7—C6—C5 | 119.5 (2) | H19B—C19—H19C | 109.5 |
C7—C6—H6 | 120.2 | O4—C22—H22A | 109.5 |
C5—C6—H6 | 120.2 | O4—C22—H22B | 109.5 |
C7—C8—C3 | 120.9 (2) | H22A—C22—H22B | 109.5 |
C7—C8—H8 | 119.6 | O4—C22—H22C | 109.5 |
C3—C8—H8 | 119.6 | H22A—C22—H22C | 109.5 |
C5—C4—C3 | 119.4 (2) | H22B—C22—H22C | 109.5 |
(Erlotinib-succinic-hydrate)
top
Crystal data top
C26H31N3O9 | F(000) = 1120 |
Mr = 529.54 | Dx = 1.346 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.4269 (16) Å | Cell parameters from 6664 reflections |
b = 24.169 (3) Å | θ = 2.3–27.5° |
c = 8.0606 (8) Å | µ = 0.10 mm−1 |
β = 92.410 (5)° | T = 150 K |
V = 2613.5 (5) Å3 | Plate, colorless |
Z = 4 | 0.40 × 0.20 × 0.10 mm |
Data collection top
XtaLABmini diffractometer | 4111 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.152 |
Graphite monochromator | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan SADABS | h = −17→17 |
Tmin = 0.478, Tmax = 1.000 | k = −31→31 |
25590 measured reflections | l = −10→10 |
5991 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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.207 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0957P)2] where P = (Fo2 + 2Fc2)/3 |
5991 reflections | (Δ/σ)max < 0.001 |
367 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.62 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
H1 | 0.524 (3) | 0.2284 (15) | 1.326 (4) | 0.053 (9)* | |
H8A | 0.639 (4) | 0.651 (2) | 0.459 (6) | 0.093 (15)* | |
H1A | 0.490 (2) | 0.4396 (13) | 0.844 (4) | 0.038 (8)* | |
H6A | 0.907 (3) | 0.6430 (18) | −0.242 (5) | 0.069 (12)* | |
H9A | 0.056 (3) | 0.6361 (19) | 0.605 (5) | 0.070 (13)* | |
H9B | 0.037 (3) | 0.589 (2) | 0.705 (5) | 0.079 (13)* | |
O1 | 0.23945 (12) | 0.61475 (6) | 0.4591 (2) | 0.0292 (4) | |
O3 | 0.20482 (11) | 0.52323 (6) | 0.6118 (2) | 0.0285 (4) | |
N3 | 0.59253 (14) | 0.59839 (8) | 0.5888 (2) | 0.0276 (4) | |
N2 | 0.65381 (14) | 0.52432 (8) | 0.7627 (2) | 0.0288 (4) | |
O7 | 0.63193 (14) | 0.61852 (7) | 0.1826 (2) | 0.0417 (5) | |
C14 | 0.30228 (16) | 0.53873 (9) | 0.6127 (3) | 0.0247 (4) | |
C12 | 0.47799 (16) | 0.52929 (9) | 0.6853 (3) | 0.0232 (4) | |
C10 | 0.66287 (17) | 0.57039 (10) | 0.6723 (3) | 0.0295 (5) | |
H10 | 0.7271 | 0.5846 | 0.6677 | 0.035* | |
N1 | 0.54851 (14) | 0.45464 (8) | 0.8511 (2) | 0.0248 (4) | |
O2 | 0.09868 (14) | 0.70254 (8) | 0.4636 (2) | 0.0426 (5) | |
C11 | 0.49703 (16) | 0.57823 (9) | 0.5971 (3) | 0.0238 (4) | |
C9 | 0.56223 (16) | 0.50246 (9) | 0.7669 (3) | 0.0235 (4) | |
O4 | 0.02620 (12) | 0.51222 (8) | 0.7678 (3) | 0.0398 (4) | |
C6 | 0.72089 (17) | 0.42703 (10) | 0.9438 (3) | 0.0291 (5) | |
H6 | 0.7490 | 0.4567 | 0.8891 | 0.035* | |
O8 | 0.66565 (16) | 0.67408 (8) | 0.3992 (2) | 0.0424 (5) | |
C7 | 0.61776 (16) | 0.41961 (9) | 0.9375 (3) | 0.0239 (4) | |
O6 | 0.85498 (16) | 0.65925 (9) | −0.2278 (3) | 0.0450 (5) | |
C13 | 0.37889 (16) | 0.50980 (9) | 0.6910 (3) | 0.0248 (4) | |
H13 | 0.3655 | 0.4773 | 0.7479 | 0.030* | |
C20 | 0.18277 (17) | 0.47441 (10) | 0.7053 (3) | 0.0311 (5) | |
H20A | 0.2057 | 0.4789 | 0.8202 | 0.037* | |
H20B | 0.2162 | 0.4426 | 0.6599 | 0.037* | |
C15 | 0.32198 (16) | 0.58890 (9) | 0.5261 (3) | 0.0245 (4) | |
C16 | 0.41793 (17) | 0.60780 (9) | 0.5166 (3) | 0.0258 (5) | |
H16 | 0.4309 | 0.6399 | 0.4575 | 0.031* | |
C3 | 0.63817 (17) | 0.33729 (9) | 1.1080 (3) | 0.0271 (5) | |
C8 | 0.57718 (16) | 0.37486 (9) | 1.0196 (3) | 0.0253 (4) | |
H8 | 0.5084 | 0.3699 | 1.0155 | 0.030* | |
C17 | 0.25426 (18) | 0.66715 (9) | 0.3801 (3) | 0.0306 (5) | |
H17A | 0.2966 | 0.6628 | 0.2864 | 0.037* | |
H17B | 0.2860 | 0.6929 | 0.4578 | 0.037* | |
C26 | 0.66898 (17) | 0.66003 (9) | 0.2427 (3) | 0.0308 (5) | |
C2 | 0.59367 (18) | 0.29179 (10) | 1.1932 (3) | 0.0318 (5) | |
C21 | 0.07192 (18) | 0.46596 (10) | 0.6945 (3) | 0.0346 (6) | |
H21A | 0.0489 | 0.4624 | 0.5793 | 0.041* | |
H21B | 0.0546 | 0.4324 | 0.7525 | 0.041* | |
C4 | 0.74181 (18) | 0.34489 (10) | 1.1147 (3) | 0.0320 (5) | |
H4 | 0.7834 | 0.3203 | 1.1732 | 0.038* | |
C18 | 0.15364 (19) | 0.68839 (10) | 0.3226 (3) | 0.0338 (5) | |
H18A | 0.1612 | 0.7207 | 0.2528 | 0.041* | |
H18B | 0.1183 | 0.6602 | 0.2578 | 0.041* | |
O9 | 0.02699 (17) | 0.62280 (11) | 0.6818 (4) | 0.0574 (6) | |
C5 | 0.78131 (18) | 0.38981 (11) | 1.0324 (3) | 0.0328 (5) | |
H5 | 0.8500 | 0.3951 | 1.0368 | 0.039* | |
C1 | 0.5566 (2) | 0.25471 (12) | 1.2644 (4) | 0.0415 (6) | |
O5 | 0.8929 (2) | 0.64474 (11) | 0.0423 (3) | 0.0680 (7) | |
C23 | 0.8361 (2) | 0.66106 (11) | −0.0665 (3) | 0.0430 (7) | |
C22 | −0.0755 (2) | 0.50171 (15) | 0.8004 (4) | 0.0516 (8) | |
H22A | −0.1039 | 0.5338 | 0.8501 | 0.077* | |
H22B | −0.0795 | 0.4709 | 0.8749 | 0.077* | |
H22C | −0.1116 | 0.4933 | 0.6982 | 0.077* | |
C25 | 0.7183 (3) | 0.70376 (14) | 0.1384 (4) | 0.0523 (7) | |
H25A | 0.6771 | 0.7367 | 0.1369 | 0.063* | |
H25B | 0.7820 | 0.7134 | 0.1919 | 0.063* | |
C24 | 0.7356 (3) | 0.68695 (16) | −0.0397 (4) | 0.0566 (8) | |
H24A | 0.6841 | 0.6609 | −0.0754 | 0.068* | |
H24B | 0.7285 | 0.7195 | −0.1098 | 0.068* | |
C19 | 0.0063 (3) | 0.72810 (18) | 0.4159 (5) | 0.0663 (10) | |
H19A | −0.0290 | 0.7373 | 0.5134 | 0.100* | |
H19B | −0.0331 | 0.7031 | 0.3480 | 0.100* | |
H19C | 0.0187 | 0.7612 | 0.3543 | 0.100* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0272 (8) | 0.0229 (8) | 0.0372 (9) | 0.0005 (6) | −0.0001 (7) | 0.0056 (7) |
O3 | 0.0207 (7) | 0.0246 (8) | 0.0400 (9) | −0.0035 (6) | −0.0006 (7) | 0.0081 (7) |
N3 | 0.0264 (9) | 0.0238 (9) | 0.0329 (10) | −0.0052 (7) | 0.0045 (8) | −0.0007 (8) |
N2 | 0.0229 (9) | 0.0277 (10) | 0.0359 (10) | −0.0054 (7) | 0.0021 (8) | 0.0000 (8) |
O7 | 0.0419 (10) | 0.0337 (10) | 0.0487 (11) | −0.0107 (8) | −0.0096 (9) | 0.0054 (8) |
C14 | 0.0233 (10) | 0.0242 (10) | 0.0268 (10) | −0.0021 (8) | 0.0020 (8) | −0.0019 (9) |
C12 | 0.0239 (10) | 0.0211 (10) | 0.0247 (10) | −0.0008 (8) | 0.0041 (8) | −0.0042 (8) |
C10 | 0.0227 (10) | 0.0291 (11) | 0.0368 (12) | −0.0054 (8) | 0.0038 (9) | −0.0001 (9) |
N1 | 0.0203 (9) | 0.0237 (9) | 0.0306 (9) | −0.0019 (7) | 0.0012 (7) | 0.0011 (7) |
O2 | 0.0454 (11) | 0.0421 (11) | 0.0405 (10) | 0.0197 (8) | 0.0027 (8) | 0.0036 (8) |
C11 | 0.0242 (10) | 0.0227 (10) | 0.0251 (10) | −0.0019 (8) | 0.0062 (8) | −0.0046 (8) |
C9 | 0.0242 (10) | 0.0229 (10) | 0.0236 (10) | −0.0016 (8) | 0.0042 (8) | −0.0040 (8) |
O4 | 0.0199 (8) | 0.0408 (10) | 0.0593 (11) | −0.0030 (7) | 0.0076 (8) | 0.0070 (9) |
C6 | 0.0244 (11) | 0.0294 (11) | 0.0336 (12) | −0.0011 (8) | 0.0027 (9) | −0.0004 (9) |
O8 | 0.0551 (12) | 0.0303 (10) | 0.0427 (11) | −0.0139 (8) | 0.0119 (9) | 0.0030 (8) |
C7 | 0.0229 (10) | 0.0260 (11) | 0.0230 (10) | 0.0012 (8) | 0.0016 (8) | −0.0033 (8) |
O6 | 0.0364 (11) | 0.0551 (13) | 0.0436 (11) | −0.0055 (9) | 0.0010 (9) | 0.0009 (9) |
C13 | 0.0246 (10) | 0.0211 (10) | 0.0288 (11) | −0.0003 (8) | 0.0030 (9) | −0.0002 (8) |
C20 | 0.0247 (11) | 0.0257 (11) | 0.0427 (13) | −0.0034 (8) | 0.0001 (10) | 0.0105 (10) |
C15 | 0.0261 (11) | 0.0218 (10) | 0.0256 (10) | 0.0024 (8) | 0.0023 (9) | −0.0020 (8) |
C16 | 0.0302 (11) | 0.0206 (10) | 0.0267 (11) | −0.0024 (8) | 0.0045 (9) | −0.0006 (8) |
C3 | 0.0301 (11) | 0.0240 (11) | 0.0270 (10) | −0.0007 (8) | 0.0005 (9) | −0.0022 (9) |
C8 | 0.0257 (10) | 0.0250 (10) | 0.0251 (10) | 0.0000 (8) | 0.0008 (9) | −0.0032 (8) |
C17 | 0.0348 (12) | 0.0229 (11) | 0.0339 (12) | −0.0014 (9) | 0.0003 (10) | 0.0036 (9) |
C26 | 0.0246 (11) | 0.0260 (11) | 0.0417 (13) | −0.0007 (8) | 0.0008 (10) | 0.0047 (10) |
C2 | 0.0337 (12) | 0.0288 (12) | 0.0326 (12) | 0.0039 (9) | −0.0020 (10) | 0.0001 (10) |
C21 | 0.0268 (12) | 0.0286 (12) | 0.0480 (14) | −0.0074 (9) | −0.0037 (10) | 0.0091 (10) |
C4 | 0.0301 (12) | 0.0332 (12) | 0.0325 (12) | 0.0072 (9) | −0.0028 (10) | −0.0008 (10) |
C18 | 0.0398 (13) | 0.0288 (12) | 0.0326 (12) | 0.0044 (10) | −0.0002 (10) | 0.0027 (10) |
O9 | 0.0424 (12) | 0.0489 (14) | 0.0818 (18) | 0.0049 (10) | 0.0142 (12) | 0.0157 (13) |
C5 | 0.0240 (11) | 0.0382 (13) | 0.0360 (12) | 0.0013 (9) | −0.0003 (9) | 0.0006 (10) |
C1 | 0.0450 (15) | 0.0346 (14) | 0.0452 (14) | 0.0010 (11) | 0.0047 (12) | 0.0081 (12) |
O5 | 0.0857 (19) | 0.0609 (15) | 0.0559 (13) | 0.0115 (13) | −0.0136 (13) | 0.0118 (12) |
C23 | 0.0549 (17) | 0.0329 (13) | 0.0408 (14) | −0.0180 (12) | −0.0023 (13) | 0.0080 (11) |
C22 | 0.0227 (12) | 0.074 (2) | 0.0581 (18) | −0.0052 (12) | 0.0062 (12) | 0.0202 (16) |
C25 | 0.0584 (19) | 0.0439 (16) | 0.0554 (17) | −0.0144 (14) | 0.0136 (15) | 0.0054 (14) |
C24 | 0.0525 (18) | 0.070 (2) | 0.0483 (17) | −0.0063 (16) | 0.0092 (14) | 0.0078 (16) |
C19 | 0.056 (2) | 0.080 (3) | 0.064 (2) | 0.0369 (18) | 0.0022 (17) | 0.0089 (19) |
Geometric parameters (Å, º) top
O1—C15 | 1.364 (3) | C15—C16 | 1.372 (3) |
O1—C17 | 1.435 (3) | C16—H16 | 0.9300 |
O3—C14 | 1.361 (3) | C3—C8 | 1.398 (3) |
O3—C20 | 1.438 (3) | C3—C4 | 1.402 (3) |
N3—C10 | 1.323 (3) | C3—C2 | 1.440 (3) |
N3—C11 | 1.376 (3) | C8—H8 | 0.9300 |
N2—C10 | 1.339 (3) | C17—C18 | 1.500 (3) |
N2—C9 | 1.340 (3) | C17—H17A | 0.9700 |
O7—C26 | 1.212 (3) | C17—H17B | 0.9700 |
C14—C13 | 1.375 (3) | C26—C25 | 1.520 (4) |
C14—C15 | 1.429 (3) | C2—C1 | 1.185 (4) |
C12—C11 | 1.409 (3) | C21—H21A | 0.9700 |
C12—C13 | 1.414 (3) | C21—H21B | 0.9700 |
C12—C9 | 1.439 (3) | C4—C5 | 1.389 (4) |
C10—H10 | 0.9300 | C4—H4 | 0.9300 |
N1—C9 | 1.357 (3) | C18—H18A | 0.9700 |
N1—C7 | 1.419 (3) | C18—H18B | 0.9700 |
N1—H1A | 0.87 (3) | O9—H9A | 0.82 (5) |
O2—C18 | 1.423 (3) | O9—H9B | 0.86 (5) |
O2—C19 | 1.424 (3) | C5—H5 | 0.9300 |
C11—C16 | 1.415 (3) | C1—H1 | 0.93 (4) |
O4—C21 | 1.417 (3) | O5—C23 | 1.204 (4) |
O4—C22 | 1.424 (3) | C23—C24 | 1.511 (5) |
C6—C5 | 1.389 (3) | C22—H22A | 0.9600 |
C6—C7 | 1.395 (3) | C22—H22B | 0.9600 |
C6—H6 | 0.9300 | C22—H22C | 0.9600 |
O8—C26 | 1.309 (3) | C25—C24 | 1.520 (5) |
O8—H8A | 0.82 (5) | C25—H25A | 0.9700 |
C7—C8 | 1.391 (3) | C25—H25B | 0.9700 |
O6—C23 | 1.336 (4) | C24—H24A | 0.9700 |
O6—H6A | 0.82 (4) | C24—H24B | 0.9700 |
C13—H13 | 0.9300 | C19—H19A | 0.9600 |
C20—C21 | 1.501 (3) | C19—H19B | 0.9600 |
C20—H20A | 0.9700 | C19—H19C | 0.9600 |
C20—H20B | 0.9700 | | |
| | | |
C15—O1—C17 | 117.04 (17) | C18—C17—H17A | 110.2 |
C14—O3—C20 | 116.25 (17) | O1—C17—H17B | 110.2 |
C10—N3—C11 | 116.16 (19) | C18—C17—H17B | 110.2 |
C10—N2—C9 | 116.50 (19) | H17A—C17—H17B | 108.5 |
O3—C14—C13 | 124.3 (2) | O7—C26—O8 | 124.8 (2) |
O3—C14—C15 | 115.38 (18) | O7—C26—C25 | 122.4 (2) |
C13—C14—C15 | 120.4 (2) | O8—C26—C25 | 112.7 (2) |
C11—C12—C13 | 119.2 (2) | C1—C2—C3 | 179.3 (3) |
C11—C12—C9 | 116.95 (19) | O4—C21—C20 | 108.32 (19) |
C13—C12—C9 | 123.9 (2) | O4—C21—H21A | 110.0 |
N3—C10—N2 | 128.5 (2) | C20—C21—H21A | 110.0 |
N3—C10—H10 | 115.7 | O4—C21—H21B | 110.0 |
N2—C10—H10 | 115.7 | C20—C21—H21B | 110.0 |
C9—N1—C7 | 130.85 (19) | H21A—C21—H21B | 108.4 |
C9—N1—H1A | 118 (2) | C5—C4—C3 | 118.8 (2) |
C7—N1—H1A | 111 (2) | C5—C4—H4 | 120.6 |
C18—O2—C19 | 111.3 (2) | C3—C4—H4 | 120.6 |
N3—C11—C12 | 120.7 (2) | O2—C18—C17 | 109.01 (19) |
N3—C11—C16 | 118.8 (2) | O2—C18—H18A | 109.9 |
C12—C11—C16 | 120.46 (19) | C17—C18—H18A | 109.9 |
N2—C9—N1 | 119.5 (2) | O2—C18—H18B | 109.9 |
N2—C9—C12 | 121.0 (2) | C17—C18—H18B | 109.9 |
N1—C9—C12 | 119.47 (19) | H18A—C18—H18B | 108.3 |
C21—O4—C22 | 111.8 (2) | H9A—O9—H9B | 118 (4) |
C5—C6—C7 | 119.5 (2) | C6—C5—C4 | 121.7 (2) |
C5—C6—H6 | 120.2 | C6—C5—H5 | 119.2 |
C7—C6—H6 | 120.2 | C4—C5—H5 | 119.2 |
C26—O8—H8A | 115 (3) | C2—C1—H1 | 174 (2) |
C8—C7—C6 | 119.4 (2) | O5—C23—O6 | 123.9 (3) |
C8—C7—N1 | 115.84 (19) | O5—C23—C24 | 125.0 (3) |
C6—C7—N1 | 124.8 (2) | O6—C23—C24 | 111.1 (3) |
C23—O6—H6A | 110 (3) | O4—C22—H22A | 109.5 |
C14—C13—C12 | 120.2 (2) | O4—C22—H22B | 109.5 |
C14—C13—H13 | 119.9 | H22A—C22—H22B | 109.5 |
C12—C13—H13 | 119.9 | O4—C22—H22C | 109.5 |
O3—C20—C21 | 107.86 (18) | H22A—C22—H22C | 109.5 |
O3—C20—H20A | 110.1 | H22B—C22—H22C | 109.5 |
C21—C20—H20A | 110.1 | C24—C25—C26 | 115.1 (3) |
O3—C20—H20B | 110.1 | C24—C25—H25A | 108.5 |
C21—C20—H20B | 110.1 | C26—C25—H25A | 108.5 |
H20A—C20—H20B | 108.4 | C24—C25—H25B | 108.5 |
O1—C15—C16 | 125.1 (2) | C26—C25—H25B | 108.5 |
O1—C15—C14 | 114.71 (18) | H25A—C25—H25B | 107.5 |
C16—C15—C14 | 120.22 (19) | C23—C24—C25 | 114.7 (3) |
C15—C16—C11 | 119.6 (2) | C23—C24—H24A | 108.6 |
C15—C16—H16 | 120.2 | C25—C24—H24A | 108.6 |
C11—C16—H16 | 120.2 | C23—C24—H24B | 108.6 |
C8—C3—C4 | 119.6 (2) | C25—C24—H24B | 108.6 |
C8—C3—C2 | 119.6 (2) | H24A—C24—H24B | 107.6 |
C4—C3—C2 | 120.8 (2) | O2—C19—H19A | 109.5 |
C7—C8—C3 | 121.0 (2) | O2—C19—H19B | 109.5 |
C7—C8—H8 | 119.5 | H19A—C19—H19B | 109.5 |
C3—C8—H8 | 119.5 | O2—C19—H19C | 109.5 |
O1—C17—C18 | 107.41 (19) | H19A—C19—H19C | 109.5 |
O1—C17—H17A | 110.2 | H19B—C19—H19C | 109.5 |
Crystal data top
C23H27N5O5 | Dx = 1.321 Mg m−3 |
Mr = 453.50 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pccn | Cell parameters from 10204 reflections |
a = 21.6051 (16) Å | θ = 2.3–27.5° |
b = 23.7024 (18) Å | µ = 0.10 mm−1 |
c = 8.9076 (6) Å | T = 150 K |
V = 4561.5 (6) Å3 | Plate, colorless |
Z = 8 | 0.24 × 0.16 × 0.08 mm |
F(000) = 1920 | |
Data collection top
XtaLABmini diffractometer | 4257 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.118 |
Graphite monochromator | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan SADABS | h = −28→28 |
Tmin = 0.799, Tmax = 1.000 | k = −30→30 |
45968 measured reflections | l = −11→11 |
5241 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.086P)2 + 1.4833P] where P = (Fo2 + 2Fc2)/3 |
5241 reflections | (Δ/σ)max = 0.001 |
320 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
C23 | 0.97369 (8) | 0.55831 (7) | 0.8333 (2) | 0.0258 (4) | |
C2 | 0.05151 (10) | 0.73571 (8) | 1.0465 (3) | 0.0375 (5) | |
H4A | 0.9208 (12) | 0.5974 (10) | 0.695 (3) | 0.044 (7)* | |
H5C | 0.8909 (12) | 0.5382 (10) | 0.877 (3) | 0.041 (6)* | |
H5B | 0.9400 (12) | 0.5097 (11) | 0.973 (3) | 0.044 (7)* | |
H4B | 0.9885 (14) | 0.6035 (12) | 0.664 (3) | 0.055 (8)* | |
H2 | 0.1166 (12) | 0.5597 (10) | 0.862 (3) | 0.045 (7)* | |
C15 | 0.22620 (8) | 0.40557 (8) | 0.5989 (2) | 0.0284 (4) | |
H15 | 0.2589 | 0.3860 | 0.5552 | 0.034* | |
C16 | 0.16617 (8) | 0.38958 (7) | 0.5694 (2) | 0.0268 (4) | |
O3 | 0.05852 (5) | 0.39718 (5) | 0.60995 (15) | 0.0291 (3) | |
O1 | 0.14779 (6) | 0.34581 (5) | 0.48118 (16) | 0.0320 (3) | |
O5 | 1.02867 (6) | 0.54857 (5) | 0.86776 (15) | 0.0296 (3) | |
N2 | 0.26275 (7) | 0.54111 (7) | 0.88582 (19) | 0.0298 (4) | |
O2 | 0.14998 (7) | 0.22517 (6) | 0.47924 (16) | 0.0368 (3) | |
O4 | −0.06612 (6) | 0.39654 (6) | 0.49988 (15) | 0.0337 (3) | |
N3 | 0.29912 (7) | 0.46440 (7) | 0.73139 (19) | 0.0304 (4) | |
N1 | 0.15812 (7) | 0.56614 (6) | 0.89440 (18) | 0.0285 (3) | |
N5 | 0.92689 (8) | 0.53351 (8) | 0.9064 (2) | 0.0343 (4) | |
C9 | 0.20437 (8) | 0.53092 (7) | 0.8471 (2) | 0.0257 (4) | |
C11 | 0.23853 (8) | 0.45183 (7) | 0.6955 (2) | 0.0265 (4) | |
C10 | 0.30616 (8) | 0.50676 (8) | 0.8250 (2) | 0.0319 (4) | |
H10 | 0.3467 | 0.5142 | 0.8536 | 0.038* | |
C7 | 0.16113 (8) | 0.61570 (7) | 0.9835 (2) | 0.0274 (4) | |
C21 | −0.04990 (8) | 0.38991 (8) | 0.6536 (2) | 0.0286 (4) | |
H21A | −0.0422 | 0.3504 | 0.6752 | 0.034* | |
H21B | −0.0836 | 0.4027 | 0.7169 | 0.034* | |
C14 | 0.11570 (8) | 0.41956 (8) | 0.6362 (2) | 0.0259 (4) | |
C13 | 0.12697 (8) | 0.46658 (7) | 0.7220 (2) | 0.0259 (4) | |
H13 | 0.0940 | 0.4876 | 0.7592 | 0.031* | |
C17 | 0.19459 (9) | 0.31212 (8) | 0.4087 (2) | 0.0324 (4) | |
H17A | 0.2272 | 0.3027 | 0.4792 | 0.039* | |
H17B | 0.2127 | 0.3327 | 0.3255 | 0.039* | |
C12 | 0.18837 (8) | 0.48336 (7) | 0.75412 (19) | 0.0248 (4) | |
C4 | 0.15411 (10) | 0.71341 (9) | 1.1599 (2) | 0.0380 (5) | |
H4 | 0.1523 | 0.7458 | 1.2187 | 0.046* | |
C22 | −0.12355 (9) | 0.36924 (9) | 0.4670 (2) | 0.0352 (4) | |
H22A | −0.1205 | 0.3299 | 0.4918 | 0.053* | |
H22B | −0.1327 | 0.3732 | 0.3620 | 0.053* | |
H22C | −0.1560 | 0.3863 | 0.5250 | 0.053* | |
C3 | 0.10622 (9) | 0.70075 (8) | 1.0593 (2) | 0.0316 (4) | |
C8 | 0.11031 (8) | 0.65226 (8) | 0.9711 (2) | 0.0296 (4) | |
H8 | 0.0789 | 0.6441 | 0.9031 | 0.036* | |
N4 | 0.95966 (9) | 0.59515 (9) | 0.7233 (2) | 0.0410 (4) | |
C18 | 0.16341 (9) | 0.25944 (8) | 0.3530 (2) | 0.0329 (4) | |
H18A | 0.1255 | 0.2690 | 0.3004 | 0.039* | |
H18B | 0.1905 | 0.2394 | 0.2843 | 0.039* | |
C6 | 0.20842 (9) | 0.62846 (8) | 1.0842 (2) | 0.0326 (4) | |
H6 | 0.2424 | 0.6047 | 1.0937 | 0.039* | |
C20 | 0.00730 (8) | 0.42401 (8) | 0.6851 (2) | 0.0298 (4) | |
H20A | 0.0021 | 0.4622 | 0.6484 | 0.036* | |
H20B | 0.0149 | 0.4256 | 0.7924 | 0.036* | |
C5 | 0.20409 (10) | 0.67730 (9) | 1.1706 (2) | 0.0382 (5) | |
H5 | 0.2358 | 0.6858 | 1.2374 | 0.046* | |
C19 | 0.12146 (11) | 0.17308 (9) | 0.4387 (3) | 0.0487 (6) | |
H19A | 0.0857 | 0.1804 | 0.3779 | 0.073* | |
H19B | 0.1092 | 0.1533 | 0.5279 | 0.073* | |
H19C | 0.1503 | 0.1505 | 0.3831 | 0.073* | |
C1 | 0.00622 (11) | 0.76373 (9) | 1.0323 (3) | 0.0476 (6) | |
H1 | −0.0292 | 0.7856 | 1.0211 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C23 | 0.0208 (8) | 0.0263 (8) | 0.0302 (9) | 0.0040 (6) | −0.0012 (7) | −0.0028 (7) |
C2 | 0.0361 (11) | 0.0268 (9) | 0.0497 (12) | −0.0051 (8) | 0.0077 (9) | −0.0022 (9) |
C15 | 0.0205 (8) | 0.0287 (9) | 0.0361 (10) | 0.0045 (7) | 0.0042 (7) | 0.0036 (8) |
C16 | 0.0227 (8) | 0.0257 (8) | 0.0320 (9) | 0.0017 (6) | 0.0009 (7) | 0.0014 (7) |
O3 | 0.0172 (6) | 0.0324 (7) | 0.0378 (7) | 0.0008 (5) | 0.0006 (5) | −0.0066 (5) |
O1 | 0.0234 (7) | 0.0296 (7) | 0.0431 (8) | 0.0041 (5) | 0.0016 (5) | −0.0081 (6) |
O5 | 0.0175 (6) | 0.0303 (7) | 0.0409 (7) | 0.0011 (5) | −0.0006 (5) | 0.0027 (5) |
N2 | 0.0189 (7) | 0.0292 (8) | 0.0414 (9) | −0.0018 (6) | 0.0002 (6) | 0.0031 (7) |
O2 | 0.0427 (8) | 0.0308 (7) | 0.0370 (8) | −0.0066 (6) | 0.0023 (6) | −0.0060 (6) |
O4 | 0.0236 (7) | 0.0429 (8) | 0.0346 (7) | −0.0055 (6) | −0.0013 (5) | 0.0042 (6) |
N3 | 0.0172 (7) | 0.0310 (8) | 0.0431 (9) | −0.0003 (6) | 0.0031 (6) | 0.0040 (7) |
N1 | 0.0186 (7) | 0.0274 (8) | 0.0395 (9) | 0.0002 (6) | −0.0004 (6) | −0.0022 (6) |
N5 | 0.0166 (8) | 0.0456 (10) | 0.0409 (9) | 0.0012 (7) | −0.0023 (7) | 0.0100 (8) |
C9 | 0.0185 (8) | 0.0261 (8) | 0.0324 (9) | −0.0008 (6) | 0.0026 (6) | 0.0061 (7) |
C11 | 0.0190 (8) | 0.0282 (9) | 0.0323 (9) | 0.0003 (6) | 0.0022 (7) | 0.0064 (7) |
C10 | 0.0163 (8) | 0.0330 (10) | 0.0463 (11) | −0.0014 (7) | 0.0002 (7) | 0.0036 (8) |
C7 | 0.0241 (9) | 0.0259 (8) | 0.0323 (9) | −0.0034 (7) | 0.0044 (7) | 0.0023 (7) |
C21 | 0.0205 (8) | 0.0338 (9) | 0.0316 (9) | −0.0013 (7) | 0.0012 (7) | −0.0015 (7) |
C14 | 0.0174 (8) | 0.0285 (9) | 0.0317 (9) | 0.0023 (6) | −0.0008 (7) | 0.0038 (7) |
C13 | 0.0190 (8) | 0.0283 (9) | 0.0305 (9) | 0.0037 (6) | 0.0019 (7) | 0.0014 (7) |
C17 | 0.0262 (9) | 0.0314 (9) | 0.0397 (10) | 0.0064 (7) | 0.0082 (8) | −0.0019 (8) |
C12 | 0.0190 (8) | 0.0255 (8) | 0.0300 (9) | 0.0006 (6) | 0.0013 (6) | 0.0051 (7) |
C4 | 0.0391 (11) | 0.0324 (10) | 0.0425 (11) | −0.0066 (8) | 0.0035 (9) | −0.0057 (9) |
C22 | 0.0234 (9) | 0.0406 (11) | 0.0415 (11) | 0.0016 (8) | −0.0038 (8) | −0.0052 (9) |
C3 | 0.0299 (9) | 0.0248 (9) | 0.0400 (10) | −0.0043 (7) | 0.0061 (8) | 0.0021 (8) |
C8 | 0.0235 (9) | 0.0289 (9) | 0.0365 (10) | −0.0025 (7) | 0.0019 (7) | 0.0025 (8) |
N4 | 0.0304 (10) | 0.0530 (11) | 0.0395 (10) | 0.0081 (8) | 0.0010 (8) | 0.0146 (9) |
C18 | 0.0312 (10) | 0.0370 (10) | 0.0306 (9) | 0.0066 (8) | 0.0005 (8) | −0.0045 (8) |
C6 | 0.0247 (9) | 0.0356 (10) | 0.0376 (10) | −0.0019 (7) | −0.0007 (7) | 0.0032 (8) |
C20 | 0.0196 (8) | 0.0329 (9) | 0.0368 (10) | 0.0020 (7) | 0.0032 (7) | −0.0062 (8) |
C5 | 0.0330 (10) | 0.0406 (11) | 0.0409 (11) | −0.0074 (9) | −0.0047 (8) | −0.0036 (9) |
C19 | 0.0441 (13) | 0.0322 (11) | 0.0700 (16) | −0.0050 (9) | −0.0033 (11) | −0.0132 (10) |
C1 | 0.0350 (11) | 0.0325 (11) | 0.0754 (16) | 0.0012 (9) | 0.0084 (11) | −0.0009 (11) |
Geometric parameters (Å, º) top
C23—O5 | 1.248 (2) | C21—C20 | 1.503 (2) |
C23—N5 | 1.339 (2) | C21—H21A | 0.9700 |
C23—N4 | 1.347 (2) | C21—H21B | 0.9700 |
C2—C1 | 1.189 (3) | C14—C13 | 1.373 (3) |
C2—C3 | 1.448 (3) | C13—C12 | 1.414 (2) |
C15—C16 | 1.377 (2) | C13—H13 | 0.9300 |
C15—C11 | 1.419 (3) | C17—C18 | 1.503 (3) |
C15—H15 | 0.9300 | C17—H17A | 0.9700 |
C16—O1 | 1.361 (2) | C17—H17B | 0.9700 |
C16—C14 | 1.431 (2) | C4—C5 | 1.381 (3) |
O3—C14 | 1.365 (2) | C4—C3 | 1.401 (3) |
O3—C20 | 1.441 (2) | C4—H4 | 0.9300 |
O1—C17 | 1.441 (2) | C22—H22A | 0.9600 |
N2—C9 | 1.330 (2) | C22—H22B | 0.9600 |
N2—C10 | 1.355 (2) | C22—H22C | 0.9600 |
O2—C18 | 1.417 (2) | C3—C8 | 1.395 (3) |
O2—C19 | 1.426 (2) | C8—H8 | 0.9300 |
O4—C21 | 1.422 (2) | N4—H4A | 0.88 (3) |
O4—C22 | 1.430 (2) | N4—H4B | 0.84 (3) |
N3—C10 | 1.314 (3) | C18—H18A | 0.9700 |
N3—C11 | 1.380 (2) | C18—H18B | 0.9700 |
N1—C9 | 1.368 (2) | C6—C5 | 1.393 (3) |
N1—C7 | 1.419 (2) | C6—H6 | 0.9300 |
N1—H2 | 0.96 (3) | C20—H20A | 0.9700 |
N5—H5C | 0.83 (3) | C20—H20B | 0.9700 |
N5—H5B | 0.86 (3) | C5—H5 | 0.9300 |
C9—C12 | 1.441 (3) | C19—H19A | 0.9600 |
C11—C12 | 1.416 (2) | C19—H19B | 0.9600 |
C10—H10 | 0.9300 | C19—H19C | 0.9600 |
C7—C6 | 1.393 (3) | C1—H1 | 0.9300 |
C7—C8 | 1.403 (3) | | |
| | | |
O5—C23—N5 | 121.19 (17) | O1—C17—H17B | 110.3 |
O5—C23—N4 | 120.85 (17) | C18—C17—H17B | 110.3 |
N5—C23—N4 | 117.94 (17) | H17A—C17—H17B | 108.6 |
C1—C2—C3 | 178.2 (3) | C13—C12—C11 | 119.65 (16) |
C16—C15—C11 | 120.35 (16) | C13—C12—C9 | 124.14 (16) |
C16—C15—H15 | 119.8 | C11—C12—C9 | 116.19 (15) |
C11—C15—H15 | 119.8 | C5—C4—C3 | 119.26 (19) |
O1—C16—C15 | 126.51 (16) | C5—C4—H4 | 120.4 |
O1—C16—C14 | 113.35 (15) | C3—C4—H4 | 120.4 |
C15—C16—C14 | 120.13 (17) | O4—C22—H22A | 109.5 |
C14—O3—C20 | 116.36 (14) | O4—C22—H22B | 109.5 |
C16—O1—C17 | 118.46 (14) | H22A—C22—H22B | 109.5 |
C9—N2—C10 | 116.35 (16) | O4—C22—H22C | 109.5 |
C18—O2—C19 | 112.58 (17) | H22A—C22—H22C | 109.5 |
C21—O4—C22 | 111.19 (14) | H22B—C22—H22C | 109.5 |
C10—N3—C11 | 114.97 (15) | C8—C3—C4 | 119.33 (18) |
C9—N1—C7 | 130.05 (16) | C8—C3—C2 | 118.59 (18) |
C9—N1—H2 | 119.6 (15) | C4—C3—C2 | 122.05 (18) |
C7—N1—H2 | 110.3 (15) | C3—C8—C7 | 120.93 (18) |
C23—N5—H5C | 119.6 (17) | C3—C8—H8 | 119.5 |
C23—N5—H5B | 111.8 (17) | C7—C8—H8 | 119.5 |
H5C—N5—H5B | 128 (2) | C23—N4—H4A | 117.7 (16) |
N2—C9—N1 | 120.14 (17) | C23—N4—H4B | 116.3 (19) |
N2—C9—C12 | 121.23 (16) | H4A—N4—H4B | 121 (2) |
N1—C9—C12 | 118.62 (15) | O2—C18—C17 | 107.84 (15) |
N3—C11—C12 | 121.75 (17) | O2—C18—H18A | 110.1 |
N3—C11—C15 | 119.05 (16) | C17—C18—H18A | 110.1 |
C12—C11—C15 | 119.19 (16) | O2—C18—H18B | 110.1 |
N3—C10—N2 | 129.24 (17) | C17—C18—H18B | 110.1 |
N3—C10—H10 | 115.4 | H18A—C18—H18B | 108.5 |
N2—C10—H10 | 115.4 | C5—C6—C7 | 119.13 (18) |
C6—C7—C8 | 119.37 (17) | C5—C6—H6 | 120.4 |
C6—C7—N1 | 124.99 (17) | C7—C6—H6 | 120.4 |
C8—C7—N1 | 115.56 (16) | O3—C20—C21 | 107.88 (15) |
O4—C21—C20 | 108.87 (15) | O3—C20—H20A | 110.1 |
O4—C21—H21A | 109.9 | C21—C20—H20A | 110.1 |
C20—C21—H21A | 109.9 | O3—C20—H20B | 110.1 |
O4—C21—H21B | 109.9 | C21—C20—H20B | 110.1 |
C20—C21—H21B | 109.9 | H20A—C20—H20B | 108.4 |
H21A—C21—H21B | 108.3 | C4—C5—C6 | 121.97 (19) |
O3—C14—C13 | 124.84 (15) | C4—C5—H5 | 119.0 |
O3—C14—C16 | 115.19 (16) | C6—C5—H5 | 119.0 |
C13—C14—C16 | 119.96 (16) | O2—C19—H19A | 109.5 |
C14—C13—C12 | 120.48 (16) | O2—C19—H19B | 109.5 |
C14—C13—H13 | 119.8 | H19A—C19—H19B | 109.5 |
C12—C13—H13 | 119.8 | O2—C19—H19C | 109.5 |
O1—C17—C18 | 107.08 (15) | H19A—C19—H19C | 109.5 |
O1—C17—H17A | 110.3 | H19B—C19—H19C | 109.5 |
C18—C17—H17A | 110.3 | C2—C1—H1 | 180.0 |