The stoichiometry, X-ray structures and stability of four pharmaceutical cocrystals previously identified from liquid-assisted grinding (LAG) of 11-azaartemisinin (11-Aza; systematic name: 1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0
4,13.0
8,13]hexadecan-10-one) with
trans-cinnamic (Cin), maleic (Mal) and fumaric (Fum) acids are herein reported.
trans-Cinnamic acid, a mono acid, forms 1:1 cocrystal 11-Aza:Cin (
1, C
15H
23NO
4·C
9H
8O
2). Maleic acid forms both 1:1 cocrystal 11-Aza:Mal (
2, C
15H
23NO
4·C
4H
4O
4), in which one COOH group is involved in self-catenation, and 2:1 cocrystal 11-Aza
2:Mal (
3, 2C
15H
23NO
4·C
4H
4O
4). Its isomer, fumaric acid, only affords 2:1 cocrystal 11-Aza
2:Fum (
4). All cocrystal formation appears driven by acid–lactam
R22(8) heterosynthons with short O—H
O=C hydrogen bonds [O
O = 2.56 (2) Å], augmented by weaker C=O
H—N contacts. Despite a better packing efficiency, cocrystal
3 is metastable with respect to
2, probably due to a higher conformational energy for the maleic acid molecule in its structure. In each case, the microcrystalline powders from LAG were useful in providing seeding for the single-crystal growth.
Supporting information
CCDC references: 1839352; 1839351; 1839350; 1839349
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0
4,13.0
8,13]hexadecan-10-one–(2
E)-3-Phenylprop-2-enoic acid (1/1) (madiha47cult)
top
Crystal data top
C15H23NO4·C9H8O2 | Z = 2 |
Mr = 429.50 | F(000) = 460 |
Triclinic, P1 | Dx = 1.296 Mg m−3 |
a = 9.5552 (4) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 10.3175 (5) Å | Cell parameters from 8241 reflections |
c = 11.9645 (6) Å | θ = 3.9–75.3° |
α = 91.085 (4)° | µ = 0.76 mm−1 |
β = 110.515 (4)° | T = 100 K |
γ = 93.998 (3)° | Plate, colourless |
V = 1100.84 (9) Å3 | 0.2 × 0.2 × 0.03 mm |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Atlas detector | 7242 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 6766 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.032 |
Detector resolution: 10.3577 pixels mm-1 | θmax = 67.5°, θmin = 4.0° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −12→12 |
Tmin = 0.934, Tmax = 1.000 | l = −14→14 |
16397 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.042P)2 + 0.0075P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.077 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.16 e Å−3 |
7242 reflections | Δρmin = −0.18 e Å−3 |
581 parameters | Absolute structure: Flack x determined using 2859 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
3 restraints | Absolute structure parameter: −0.05 (8) |
Primary atom site location: structure-invariant direct methods | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.92939 (18) | 0.23922 (16) | 0.90910 (15) | 0.0179 (4) | |
O2 | 0.93313 (19) | 0.10373 (16) | 0.86936 (16) | 0.0196 (4) | |
O3 | 0.83959 (18) | 0.13856 (16) | 0.66720 (15) | 0.0181 (4) | |
O10 | 0.44598 (19) | 0.11831 (17) | 0.79596 (17) | 0.0231 (4) | |
N11 | 0.6261 (2) | 0.1556 (2) | 0.71765 (19) | 0.0178 (4) | |
H11 | 0.584 (3) | 0.088 (3) | 0.665 (3) | 0.023 (8)* | |
C1 | 0.8452 (2) | 0.3157 (2) | 0.8100 (2) | 0.0156 (5) | |
C2 | 0.7533 (2) | 0.2275 (2) | 0.7011 (2) | 0.0162 (5) | |
H2 | 0.7124 | 0.2849 | 0.6326 | 0.019* | |
C3 | 0.9700 (3) | 0.1068 (3) | 0.7645 (2) | 0.0199 (5) | |
C4 | 1.1033 (3) | 0.2056 (2) | 0.7772 (2) | 0.0209 (5) | |
H4A | 1.1661 | 0.2179 | 0.8628 | 0.025* | |
H4B | 1.1652 | 0.1688 | 0.7351 | 0.025* | |
C5 | 1.0595 (3) | 0.3376 (3) | 0.7283 (2) | 0.0204 (5) | |
H5A | 1.0066 | 0.3259 | 0.6409 | 0.024* | |
H5B | 1.1525 | 0.3942 | 0.7417 | 0.024* | |
C6 | 0.8854 (3) | 0.5194 (2) | 0.7022 (2) | 0.0186 (5) | |
H6 | 0.8259 | 0.4804 | 0.6207 | 0.022* | |
C7 | 0.7788 (3) | 0.5856 (2) | 0.7506 (2) | 0.0206 (5) | |
H7A | 0.8381 | 0.6343 | 0.8264 | 0.025* | |
H7B | 0.7257 | 0.6490 | 0.6928 | 0.025* | |
C8 | 0.6634 (3) | 0.4898 (2) | 0.7727 (2) | 0.0199 (5) | |
H8A | 0.5975 | 0.4463 | 0.6961 | 0.024* | |
H8B | 0.6002 | 0.5373 | 0.8070 | 0.024* | |
C9 | 0.6359 (3) | 0.2899 (2) | 0.8923 (2) | 0.0191 (5) | |
H9 | 0.7003 | 0.2458 | 0.9637 | 0.023* | |
C10 | 0.5617 (2) | 0.1829 (2) | 0.7963 (2) | 0.0178 (5) | |
C11 | 0.9596 (3) | 0.4090 (2) | 0.7818 (2) | 0.0170 (5) | |
H11B | 1.0273 | 0.4513 | 0.8597 | 0.020* | |
C12 | 0.7417 (3) | 0.3877 (2) | 0.8588 (2) | 0.0160 (5) | |
H12 | 0.8072 | 0.4358 | 0.9345 | 0.019* | |
C13 | 0.9972 (3) | −0.0316 (3) | 0.7412 (3) | 0.0254 (6) | |
H13A | 0.9165 | −0.0906 | 0.7490 | 0.038* | |
H13B | 1.0935 | −0.0525 | 0.7992 | 0.038* | |
H13C | 0.9992 | −0.0418 | 0.6601 | 0.038* | |
C14 | 1.0053 (3) | 0.6191 (2) | 0.6906 (3) | 0.0251 (6) | |
H14A | 1.0755 | 0.6477 | 0.7703 | 0.038* | |
H14B | 0.9573 | 0.6941 | 0.6491 | 0.038* | |
H14C | 1.0598 | 0.5792 | 0.6449 | 0.038* | |
C15 | 0.5199 (3) | 0.3540 (3) | 0.9310 (3) | 0.0275 (6) | |
H15A | 0.4472 | 0.3911 | 0.8618 | 0.041* | |
H15B | 0.5703 | 0.4233 | 0.9920 | 0.041* | |
H15C | 0.4677 | 0.2888 | 0.9642 | 0.041* | |
O1A | 0.30814 (19) | 0.69183 (16) | −0.03903 (15) | 0.0186 (4) | |
O2A | 0.30912 (19) | 0.55827 (16) | 0.00256 (16) | 0.0188 (4) | |
O3A | 0.39526 (18) | 0.61595 (17) | 0.20465 (15) | 0.0180 (4) | |
O10A | 0.7903 (2) | 0.64839 (19) | 0.08281 (18) | 0.0258 (4) | |
N11A | 0.6093 (2) | 0.6674 (2) | 0.15962 (19) | 0.0179 (4) | |
H11A | 0.651 (3) | 0.607 (3) | 0.213 (3) | 0.023 (8)* | |
C1A | 0.3856 (3) | 0.7863 (2) | 0.0603 (2) | 0.0164 (5) | |
C2A | 0.4764 (2) | 0.7184 (2) | 0.1714 (2) | 0.0156 (5) | |
H2A | 0.5116 | 0.7852 | 0.2392 | 0.019* | |
C3A | 0.2687 (3) | 0.5581 (2) | 0.1054 (2) | 0.0196 (5) | |
C4A | 0.1311 (3) | 0.6335 (2) | 0.0908 (2) | 0.0208 (5) | |
H4AA | 0.0684 | 0.6309 | 0.0050 | 0.025* | |
H4AB | 0.0711 | 0.5885 | 0.1334 | 0.025* | |
C5A | 0.1666 (3) | 0.7751 (3) | 0.1370 (2) | 0.0217 (5) | |
H5AA | 0.2191 | 0.7767 | 0.2246 | 0.026* | |
H5AB | 0.0707 | 0.8147 | 0.1221 | 0.026* | |
C6A | 0.3256 (3) | 0.9885 (2) | 0.1586 (2) | 0.0198 (5) | |
H6A | 0.3835 | 0.9660 | 0.2422 | 0.024* | |
C7A | 0.4308 (3) | 1.0683 (2) | 0.1120 (2) | 0.0227 (6) | |
H7AA | 0.4767 | 1.1444 | 0.1677 | 0.027* | |
H7AB | 0.3720 | 1.1013 | 0.0337 | 0.027* | |
C8A | 0.5556 (3) | 0.9919 (2) | 0.0976 (2) | 0.0196 (5) | |
H8AA | 0.6199 | 0.9640 | 0.1765 | 0.024* | |
H8AB | 0.6189 | 1.0482 | 0.0650 | 0.024* | |
C9A | 0.6023 (3) | 0.7924 (2) | −0.0146 (2) | 0.0195 (5) | |
H9A | 0.5441 | 0.7368 | −0.0878 | 0.023* | |
C10A | 0.6747 (3) | 0.6990 (2) | 0.0810 (2) | 0.0195 (5) | |
C11A | 0.2621 (3) | 0.8603 (2) | 0.0832 (2) | 0.0174 (5) | |
H11C | 0.1933 | 0.8849 | 0.0034 | 0.021* | |
C12A | 0.4872 (3) | 0.8725 (2) | 0.0131 (2) | 0.0168 (5) | |
H12A | 0.4218 | 0.9051 | −0.0644 | 0.020* | |
C13A | 0.2480 (3) | 0.4165 (3) | 0.1288 (3) | 0.0236 (6) | |
H13D | 0.3356 | 0.3728 | 0.1285 | 0.035* | |
H13E | 0.1580 | 0.3761 | 0.0663 | 0.035* | |
H13F | 0.2369 | 0.4086 | 0.2068 | 0.035* | |
C14A | 0.1971 (3) | 1.0681 (3) | 0.1616 (3) | 0.0254 (6) | |
H14D | 0.1365 | 1.0885 | 0.0800 | 0.038* | |
H14E | 0.2385 | 1.1491 | 0.2096 | 0.038* | |
H14F | 0.1340 | 1.0175 | 0.1972 | 0.038* | |
C15A | 0.7206 (3) | 0.8741 (3) | −0.0468 (3) | 0.0289 (6) | |
H15D | 0.7862 | 0.9263 | 0.0237 | 0.043* | |
H15E | 0.6712 | 0.9319 | −0.1104 | 0.043* | |
H15F | 0.7803 | 0.8167 | −0.0747 | 0.043* | |
O21 | 0.3439 (2) | −0.1075 (2) | 0.69320 (19) | 0.0321 (5) | |
H21 | 0.375 (4) | −0.021 (4) | 0.719 (3) | 0.033 (9)* | |
O22 | 0.4631 (2) | −0.08116 (19) | 0.56236 (19) | 0.0302 (4) | |
C21 | 0.3923 (3) | −0.1499 (3) | 0.6092 (3) | 0.0241 (6) | |
C22 | 0.3549 (3) | −0.2909 (3) | 0.5833 (3) | 0.0255 (6) | |
H22 | 0.2991 | −0.3361 | 0.6245 | 0.031* | |
C23 | 0.3953 (3) | −0.3579 (3) | 0.5052 (2) | 0.0228 (6) | |
H23 | 0.4416 | −0.3098 | 0.4588 | 0.027* | |
C24 | 0.3750 (3) | −0.4995 (3) | 0.4845 (2) | 0.0214 (5) | |
C25 | 0.2707 (3) | −0.5764 (3) | 0.5172 (3) | 0.0259 (6) | |
H25 | 0.2044 | −0.5358 | 0.5476 | 0.031* | |
C26 | 0.2623 (3) | −0.7104 (3) | 0.5059 (3) | 0.0284 (6) | |
H26 | 0.1913 | −0.7611 | 0.5294 | 0.034* | |
C27 | 0.3575 (3) | −0.7713 (3) | 0.4604 (3) | 0.0285 (6) | |
H27 | 0.3532 | −0.8635 | 0.4540 | 0.034* | |
C28 | 0.4586 (3) | −0.6963 (3) | 0.4245 (2) | 0.0279 (6) | |
H28 | 0.5223 | −0.7374 | 0.3917 | 0.033* | |
C29 | 0.4677 (3) | −0.5616 (3) | 0.4362 (2) | 0.0238 (6) | |
H29 | 0.5375 | −0.5112 | 0.4111 | 0.029* | |
O21A | 0.8798 (2) | 0.4353 (2) | 0.1824 (2) | 0.0307 (5) | |
H21A | 0.852 (5) | 0.523 (4) | 0.157 (4) | 0.053 (11)* | |
O22A | 0.7572 (2) | 0.4507 (2) | 0.31047 (19) | 0.0313 (5) | |
C21A | 0.8306 (3) | 0.3895 (3) | 0.2653 (3) | 0.0245 (6) | |
C22A | 0.8714 (3) | 0.2555 (3) | 0.2932 (3) | 0.0258 (6) | |
H22A | 0.9327 | 0.2173 | 0.2562 | 0.031* | |
C23A | 0.8256 (3) | 0.1862 (3) | 0.3683 (2) | 0.0224 (6) | |
H23A | 0.7725 | 0.2288 | 0.4102 | 0.027* | |
C24A | 0.8507 (3) | 0.0492 (3) | 0.3915 (2) | 0.0224 (6) | |
C25A | 0.9668 (3) | −0.0103 (3) | 0.3705 (3) | 0.0304 (6) | |
H25A | 1.0381 | 0.0409 | 0.3477 | 0.036* | |
C26A | 0.9795 (4) | −0.1421 (3) | 0.3823 (3) | 0.0391 (8) | |
H26A | 1.0587 | −0.1809 | 0.3669 | 0.047* | |
C27A | 0.8777 (4) | −0.2178 (3) | 0.4163 (3) | 0.0398 (8) | |
H27A | 0.8851 | −0.3090 | 0.4226 | 0.048* | |
C28A | 0.7651 (4) | −0.1603 (3) | 0.4412 (3) | 0.0362 (7) | |
H28A | 0.6962 | −0.2118 | 0.4663 | 0.043* | |
C29A | 0.7517 (3) | −0.0272 (3) | 0.4298 (2) | 0.0266 (6) | |
H29A | 0.6746 | 0.0116 | 0.4482 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0202 (8) | 0.0152 (8) | 0.0160 (9) | 0.0040 (6) | 0.0032 (7) | −0.0005 (7) |
O2 | 0.0238 (9) | 0.0156 (8) | 0.0198 (9) | 0.0046 (7) | 0.0077 (7) | 0.0005 (7) |
O3 | 0.0175 (8) | 0.0203 (9) | 0.0169 (9) | 0.0050 (7) | 0.0062 (7) | −0.0007 (7) |
O10 | 0.0192 (8) | 0.0226 (9) | 0.0303 (10) | −0.0013 (7) | 0.0127 (8) | −0.0013 (8) |
N11 | 0.0162 (9) | 0.0182 (10) | 0.0176 (10) | −0.0011 (8) | 0.0050 (8) | −0.0019 (9) |
C1 | 0.0133 (10) | 0.0171 (12) | 0.0159 (12) | 0.0028 (9) | 0.0041 (9) | 0.0025 (10) |
C2 | 0.0135 (10) | 0.0181 (12) | 0.0172 (12) | 0.0034 (9) | 0.0053 (9) | 0.0013 (10) |
C3 | 0.0183 (11) | 0.0226 (13) | 0.0206 (13) | 0.0069 (10) | 0.0079 (10) | 0.0037 (10) |
C4 | 0.0153 (11) | 0.0242 (13) | 0.0248 (14) | 0.0042 (10) | 0.0086 (10) | 0.0011 (11) |
C5 | 0.0167 (11) | 0.0240 (13) | 0.0225 (14) | 0.0024 (9) | 0.0093 (10) | 0.0025 (10) |
C6 | 0.0202 (12) | 0.0175 (12) | 0.0189 (12) | 0.0030 (9) | 0.0073 (10) | 0.0031 (10) |
C7 | 0.0221 (12) | 0.0178 (12) | 0.0224 (13) | 0.0061 (10) | 0.0076 (10) | 0.0048 (10) |
C8 | 0.0183 (11) | 0.0194 (12) | 0.0235 (13) | 0.0056 (9) | 0.0084 (10) | 0.0009 (10) |
C9 | 0.0183 (11) | 0.0206 (12) | 0.0195 (13) | 0.0015 (9) | 0.0080 (10) | −0.0007 (10) |
C10 | 0.0151 (11) | 0.0164 (12) | 0.0219 (13) | 0.0028 (9) | 0.0063 (10) | 0.0016 (10) |
C11 | 0.0143 (11) | 0.0191 (12) | 0.0167 (12) | 0.0023 (9) | 0.0041 (9) | 0.0008 (10) |
C12 | 0.0159 (10) | 0.0164 (11) | 0.0169 (12) | 0.0020 (9) | 0.0072 (9) | −0.0005 (10) |
C13 | 0.0274 (13) | 0.0232 (14) | 0.0282 (15) | 0.0090 (10) | 0.0117 (11) | 0.0012 (11) |
C14 | 0.0275 (13) | 0.0187 (13) | 0.0299 (15) | −0.0005 (10) | 0.0115 (11) | 0.0062 (11) |
C15 | 0.0264 (13) | 0.0266 (14) | 0.0349 (16) | −0.0007 (11) | 0.0185 (12) | −0.0060 (12) |
O1A | 0.0225 (8) | 0.0158 (8) | 0.0154 (9) | 0.0020 (7) | 0.0042 (7) | 0.0003 (7) |
O2A | 0.0230 (8) | 0.0137 (8) | 0.0200 (9) | 0.0023 (6) | 0.0076 (7) | 0.0012 (7) |
O3A | 0.0165 (8) | 0.0191 (8) | 0.0179 (9) | −0.0010 (6) | 0.0056 (7) | 0.0022 (7) |
O10A | 0.0205 (9) | 0.0256 (9) | 0.0369 (11) | 0.0081 (7) | 0.0155 (8) | 0.0090 (8) |
N11A | 0.0146 (9) | 0.0191 (10) | 0.0196 (11) | 0.0052 (8) | 0.0046 (8) | 0.0056 (9) |
C1A | 0.0153 (10) | 0.0178 (12) | 0.0149 (11) | 0.0015 (9) | 0.0037 (9) | −0.0013 (10) |
C2A | 0.0145 (11) | 0.0168 (12) | 0.0160 (12) | 0.0009 (9) | 0.0060 (9) | 0.0025 (9) |
C3A | 0.0158 (11) | 0.0220 (13) | 0.0196 (13) | 0.0002 (9) | 0.0045 (10) | 0.0008 (10) |
C4A | 0.0156 (11) | 0.0214 (13) | 0.0257 (14) | 0.0009 (9) | 0.0078 (10) | 0.0030 (11) |
C5A | 0.0187 (11) | 0.0217 (13) | 0.0266 (14) | 0.0040 (9) | 0.0101 (10) | 0.0003 (11) |
C6A | 0.0215 (12) | 0.0182 (12) | 0.0196 (12) | 0.0031 (9) | 0.0070 (10) | 0.0003 (10) |
C7A | 0.0271 (13) | 0.0173 (12) | 0.0234 (14) | 0.0021 (10) | 0.0087 (11) | 0.0005 (10) |
C8A | 0.0197 (12) | 0.0178 (12) | 0.0224 (13) | −0.0008 (9) | 0.0091 (10) | 0.0019 (10) |
C9A | 0.0197 (12) | 0.0201 (12) | 0.0208 (13) | 0.0041 (10) | 0.0091 (10) | 0.0047 (10) |
C10A | 0.0174 (11) | 0.0186 (12) | 0.0230 (13) | 0.0006 (9) | 0.0077 (10) | 0.0010 (10) |
C11A | 0.0163 (11) | 0.0174 (12) | 0.0181 (12) | 0.0041 (9) | 0.0051 (9) | 0.0016 (10) |
C12A | 0.0189 (11) | 0.0170 (12) | 0.0155 (12) | 0.0021 (9) | 0.0070 (9) | 0.0021 (10) |
C13A | 0.0221 (12) | 0.0198 (13) | 0.0276 (14) | 0.0004 (10) | 0.0073 (11) | 0.0029 (11) |
C14A | 0.0313 (14) | 0.0212 (13) | 0.0273 (14) | 0.0073 (11) | 0.0138 (12) | −0.0003 (11) |
C15A | 0.0297 (14) | 0.0271 (14) | 0.0399 (17) | 0.0081 (11) | 0.0230 (13) | 0.0129 (12) |
O21 | 0.0354 (11) | 0.0267 (11) | 0.0385 (12) | −0.0072 (8) | 0.0206 (9) | −0.0075 (9) |
O22 | 0.0379 (11) | 0.0247 (10) | 0.0326 (11) | −0.0033 (8) | 0.0192 (9) | 0.0004 (9) |
C21 | 0.0202 (12) | 0.0253 (14) | 0.0263 (14) | 0.0009 (10) | 0.0078 (11) | 0.0004 (11) |
C22 | 0.0243 (13) | 0.0244 (14) | 0.0297 (15) | −0.0040 (10) | 0.0129 (11) | 0.0018 (11) |
C23 | 0.0185 (12) | 0.0265 (14) | 0.0223 (14) | −0.0011 (10) | 0.0062 (11) | 0.0039 (11) |
C24 | 0.0191 (11) | 0.0272 (14) | 0.0165 (12) | 0.0046 (10) | 0.0040 (10) | 0.0018 (10) |
C25 | 0.0245 (13) | 0.0269 (15) | 0.0273 (15) | 0.0001 (11) | 0.0110 (11) | −0.0026 (12) |
C26 | 0.0330 (15) | 0.0264 (14) | 0.0255 (15) | −0.0039 (11) | 0.0111 (12) | 0.0015 (12) |
C27 | 0.0339 (14) | 0.0236 (14) | 0.0215 (14) | 0.0076 (11) | 0.0009 (11) | 0.0000 (11) |
C28 | 0.0254 (13) | 0.0364 (16) | 0.0208 (14) | 0.0139 (11) | 0.0047 (11) | −0.0005 (12) |
C29 | 0.0198 (12) | 0.0342 (15) | 0.0169 (13) | 0.0034 (10) | 0.0055 (10) | 0.0022 (11) |
O21A | 0.0329 (10) | 0.0290 (11) | 0.0409 (12) | 0.0123 (8) | 0.0238 (9) | 0.0148 (9) |
O22A | 0.0369 (11) | 0.0286 (11) | 0.0368 (12) | 0.0122 (9) | 0.0213 (9) | 0.0077 (9) |
C21A | 0.0181 (12) | 0.0260 (14) | 0.0289 (15) | 0.0024 (10) | 0.0076 (11) | 0.0013 (11) |
C22A | 0.0264 (13) | 0.0270 (14) | 0.0282 (15) | 0.0067 (10) | 0.0141 (11) | 0.0034 (11) |
C23A | 0.0179 (12) | 0.0271 (14) | 0.0216 (13) | 0.0036 (10) | 0.0061 (10) | −0.0015 (11) |
C24A | 0.0250 (13) | 0.0254 (14) | 0.0155 (12) | −0.0013 (10) | 0.0063 (10) | 0.0004 (10) |
C25A | 0.0374 (16) | 0.0302 (15) | 0.0284 (16) | 0.0097 (12) | 0.0162 (13) | 0.0059 (12) |
C26A | 0.058 (2) | 0.0341 (17) | 0.0297 (16) | 0.0186 (15) | 0.0187 (15) | 0.0044 (13) |
C27A | 0.066 (2) | 0.0233 (15) | 0.0205 (15) | 0.0045 (14) | 0.0036 (15) | 0.0007 (12) |
C28A | 0.0427 (17) | 0.0352 (17) | 0.0198 (15) | −0.0128 (13) | 0.0000 (13) | 0.0062 (12) |
C29A | 0.0247 (13) | 0.0337 (15) | 0.0166 (13) | −0.0026 (11) | 0.0025 (10) | 0.0013 (11) |
Geometric parameters (Å, º) top
O1—O2 | 1.475 (2) | C5A—H5AB | 0.9900 |
O1—C1 | 1.460 (3) | C5A—C11A | 1.530 (4) |
O2—C3 | 1.418 (3) | C6A—H6A | 1.0000 |
O3—C2 | 1.418 (3) | C6A—C7A | 1.514 (4) |
O3—C3 | 1.439 (3) | C6A—C11A | 1.547 (3) |
O10—C10 | 1.249 (3) | C6A—C14A | 1.535 (3) |
N11—H11 | 0.90 (3) | C7A—H7AA | 0.9900 |
N11—C2 | 1.455 (3) | C7A—H7AB | 0.9900 |
N11—C10 | 1.328 (3) | C7A—C8A | 1.531 (3) |
C1—C2 | 1.530 (3) | C8A—H8AA | 0.9900 |
C1—C11 | 1.536 (3) | C8A—H8AB | 0.9900 |
C1—C12 | 1.536 (3) | C8A—C12A | 1.531 (3) |
C2—H2 | 1.0000 | C9A—H9A | 1.0000 |
C3—C4 | 1.536 (3) | C9A—C10A | 1.515 (4) |
C3—C13 | 1.508 (3) | C9A—C12A | 1.541 (3) |
C4—H4A | 0.9900 | C9A—C15A | 1.524 (4) |
C4—H4B | 0.9900 | C11A—H11C | 1.0000 |
C4—C5 | 1.520 (4) | C12A—H12A | 1.0000 |
C5—H5A | 0.9900 | C13A—H13D | 0.9800 |
C5—H5B | 0.9900 | C13A—H13E | 0.9800 |
C5—C11 | 1.541 (3) | C13A—H13F | 0.9800 |
C6—H6 | 1.0000 | C14A—H14D | 0.9800 |
C6—C7 | 1.529 (3) | C14A—H14E | 0.9800 |
C6—C11 | 1.545 (3) | C14A—H14F | 0.9800 |
C6—C14 | 1.530 (4) | C15A—H15D | 0.9800 |
C7—H7A | 0.9900 | C15A—H15E | 0.9800 |
C7—H7B | 0.9900 | C15A—H15F | 0.9800 |
C7—C8 | 1.525 (4) | O21—H21 | 0.93 (4) |
C8—H8A | 0.9900 | O21—C21 | 1.324 (3) |
C8—H8B | 0.9900 | O22—C21 | 1.220 (4) |
C8—C12 | 1.530 (4) | C21—C22 | 1.474 (4) |
C9—H9 | 1.0000 | C22—H22 | 0.9500 |
C9—C10 | 1.520 (3) | C22—C23 | 1.329 (4) |
C9—C12 | 1.536 (4) | C23—H23 | 0.9500 |
C9—C15 | 1.528 (3) | C23—C24 | 1.465 (4) |
C11—H11B | 1.0000 | C24—C25 | 1.396 (4) |
C12—H12 | 1.0000 | C24—C29 | 1.398 (4) |
C13—H13A | 0.9800 | C25—H25 | 0.9500 |
C13—H13B | 0.9800 | C25—C26 | 1.381 (4) |
C13—H13C | 0.9800 | C26—H26 | 0.9500 |
C14—H14A | 0.9800 | C26—C27 | 1.389 (4) |
C14—H14B | 0.9800 | C27—H27 | 0.9500 |
C14—H14C | 0.9800 | C27—C28 | 1.384 (4) |
C15—H15A | 0.9800 | C28—H28 | 0.9500 |
C15—H15B | 0.9800 | C28—C29 | 1.388 (4) |
C15—H15C | 0.9800 | C29—H29 | 0.9500 |
O1A—O2A | 1.473 (2) | O21A—H21A | 0.98 (4) |
O1A—C1A | 1.466 (3) | O21A—C21A | 1.319 (4) |
O2A—C3A | 1.413 (3) | O22A—C21A | 1.224 (3) |
O3A—C2A | 1.413 (3) | C21A—C22A | 1.475 (4) |
O3A—C3A | 1.447 (3) | C22A—H22A | 0.9500 |
O10A—C10A | 1.248 (3) | C22A—C23A | 1.328 (4) |
N11A—H11A | 0.90 (3) | C23A—H23A | 0.9500 |
N11A—C2A | 1.458 (3) | C23A—C24A | 1.465 (4) |
N11A—C10A | 1.333 (4) | C24A—C25A | 1.399 (4) |
C1A—C2A | 1.524 (3) | C24A—C29A | 1.393 (4) |
C1A—C11A | 1.548 (3) | C25A—H25A | 0.9500 |
C1A—C12A | 1.528 (4) | C25A—C26A | 1.379 (4) |
C2A—H2A | 1.0000 | C26A—H26A | 0.9500 |
C3A—C4A | 1.533 (3) | C26A—C27A | 1.381 (5) |
C3A—C13A | 1.505 (4) | C27A—H27A | 0.9500 |
C4A—H4AA | 0.9900 | C27A—C28A | 1.381 (5) |
C4A—H4AB | 0.9900 | C28A—H28A | 0.9500 |
C4A—C5A | 1.524 (3) | C28A—C29A | 1.392 (4) |
C5A—H5AA | 0.9900 | C29A—H29A | 0.9500 |
| | | |
C1—O1—O2 | 111.60 (16) | C5A—C4A—H4AA | 108.6 |
C3—O2—O1 | 107.83 (17) | C5A—C4A—H4AB | 108.6 |
C2—O3—C3 | 113.49 (18) | C4A—C5A—H5AA | 108.2 |
C2—N11—H11 | 115 (2) | C4A—C5A—H5AB | 108.2 |
C10—N11—H11 | 117 (2) | C4A—C5A—C11A | 116.3 (2) |
C10—N11—C2 | 127.4 (2) | H5AA—C5A—H5AB | 107.4 |
O1—C1—C2 | 110.92 (19) | C11A—C5A—H5AA | 108.2 |
O1—C1—C11 | 107.09 (17) | C11A—C5A—H5AB | 108.2 |
O1—C1—C12 | 104.17 (19) | C7A—C6A—H6A | 108.1 |
C2—C1—C11 | 111.3 (2) | C7A—C6A—C11A | 111.8 (2) |
C2—C1—C12 | 110.68 (18) | C7A—C6A—C14A | 110.4 (2) |
C11—C1—C12 | 112.40 (19) | C11A—C6A—H6A | 108.1 |
O3—C2—N11 | 108.92 (19) | C14A—C6A—H6A | 108.1 |
O3—C2—C1 | 113.32 (18) | C14A—C6A—C11A | 110.1 (2) |
O3—C2—H2 | 107.3 | C6A—C7A—H7AA | 108.9 |
N11—C2—C1 | 112.5 (2) | C6A—C7A—H7AB | 108.9 |
N11—C2—H2 | 107.3 | C6A—C7A—C8A | 113.4 (2) |
C1—C2—H2 | 107.3 | H7AA—C7A—H7AB | 107.7 |
O2—C3—O3 | 108.00 (19) | C8A—C7A—H7AA | 108.9 |
O2—C3—C4 | 112.4 (2) | C8A—C7A—H7AB | 108.9 |
O2—C3—C13 | 104.8 (2) | C7A—C8A—H8AA | 109.7 |
O3—C3—C4 | 110.2 (2) | C7A—C8A—H8AB | 109.7 |
O3—C3—C13 | 107.2 (2) | C7A—C8A—C12A | 109.8 (2) |
C13—C3—C4 | 113.9 (2) | H8AA—C8A—H8AB | 108.2 |
C3—C4—H4A | 108.6 | C12A—C8A—H8AA | 109.7 |
C3—C4—H4B | 108.6 | C12A—C8A—H8AB | 109.7 |
H4A—C4—H4B | 107.6 | C10A—C9A—H9A | 105.8 |
C5—C4—C3 | 114.4 (2) | C10A—C9A—C12A | 113.8 (2) |
C5—C4—H4A | 108.6 | C10A—C9A—C15A | 110.9 (2) |
C5—C4—H4B | 108.6 | C12A—C9A—H9A | 105.8 |
C4—C5—H5A | 108.3 | C15A—C9A—H9A | 105.8 |
C4—C5—H5B | 108.3 | C15A—C9A—C12A | 114.0 (2) |
C4—C5—C11 | 116.1 (2) | O10A—C10A—N11A | 120.7 (2) |
H5A—C5—H5B | 107.4 | O10A—C10A—C9A | 120.3 (2) |
C11—C5—H5A | 108.3 | N11A—C10A—C9A | 119.0 (2) |
C11—C5—H5B | 108.3 | C1A—C11A—H11C | 106.7 |
C7—C6—H6 | 108.1 | C5A—C11A—C1A | 112.5 (2) |
C7—C6—C11 | 111.5 (2) | C5A—C11A—C6A | 111.4 (2) |
C7—C6—C14 | 110.5 (2) | C5A—C11A—H11C | 106.7 |
C11—C6—H6 | 108.1 | C6A—C11A—C1A | 112.39 (19) |
C14—C6—H6 | 108.1 | C6A—C11A—H11C | 106.7 |
C14—C6—C11 | 110.3 (2) | C1A—C12A—C8A | 110.5 (2) |
C6—C7—H7A | 109.0 | C1A—C12A—C9A | 110.8 (2) |
C6—C7—H7B | 109.0 | C1A—C12A—H12A | 106.9 |
H7A—C7—H7B | 107.8 | C8A—C12A—C9A | 114.6 (2) |
C8—C7—C6 | 113.0 (2) | C8A—C12A—H12A | 106.9 |
C8—C7—H7A | 109.0 | C9A—C12A—H12A | 106.9 |
C8—C7—H7B | 109.0 | C3A—C13A—H13D | 109.5 |
C7—C8—H8A | 109.6 | C3A—C13A—H13E | 109.5 |
C7—C8—H8B | 109.6 | C3A—C13A—H13F | 109.5 |
C7—C8—C12 | 110.37 (19) | H13D—C13A—H13E | 109.5 |
H8A—C8—H8B | 108.1 | H13D—C13A—H13F | 109.5 |
C12—C8—H8A | 109.6 | H13E—C13A—H13F | 109.5 |
C12—C8—H8B | 109.6 | C6A—C14A—H14D | 109.5 |
C10—C9—H9 | 106.1 | C6A—C14A—H14E | 109.5 |
C10—C9—C12 | 113.3 (2) | C6A—C14A—H14F | 109.5 |
C10—C9—C15 | 111.1 (2) | H14D—C14A—H14E | 109.5 |
C12—C9—H9 | 106.1 | H14D—C14A—H14F | 109.5 |
C15—C9—H9 | 106.1 | H14E—C14A—H14F | 109.5 |
C15—C9—C12 | 113.4 (2) | C9A—C15A—H15D | 109.5 |
O10—C10—N11 | 121.1 (2) | C9A—C15A—H15E | 109.5 |
O10—C10—C9 | 119.9 (2) | C9A—C15A—H15F | 109.5 |
N11—C10—C9 | 118.9 (2) | H15D—C15A—H15E | 109.5 |
C1—C11—C5 | 112.6 (2) | H15D—C15A—H15F | 109.5 |
C1—C11—C6 | 112.55 (19) | H15E—C15A—H15F | 109.5 |
C1—C11—H11B | 106.7 | C21—O21—H21 | 115 (2) |
C5—C11—C6 | 111.1 (2) | O21—C21—C22 | 111.4 (2) |
C5—C11—H11B | 106.7 | O22—C21—O21 | 123.9 (2) |
C6—C11—H11B | 106.7 | O22—C21—C22 | 124.6 (3) |
C1—C12—H12 | 106.9 | C21—C22—H22 | 118.4 |
C8—C12—C1 | 110.7 (2) | C23—C22—C21 | 123.3 (3) |
C8—C12—C9 | 114.8 (2) | C23—C22—H22 | 118.4 |
C8—C12—H12 | 106.9 | C22—C23—H23 | 117.1 |
C9—C12—C1 | 110.25 (19) | C22—C23—C24 | 125.8 (3) |
C9—C12—H12 | 106.9 | C24—C23—H23 | 117.1 |
C3—C13—H13A | 109.5 | C25—C24—C23 | 122.2 (2) |
C3—C13—H13B | 109.5 | C25—C24—C29 | 118.2 (2) |
C3—C13—H13C | 109.5 | C29—C24—C23 | 119.5 (3) |
H13A—C13—H13B | 109.5 | C24—C25—H25 | 119.5 |
H13A—C13—H13C | 109.5 | C26—C25—C24 | 121.1 (3) |
H13B—C13—H13C | 109.5 | C26—C25—H25 | 119.5 |
C6—C14—H14A | 109.5 | C25—C26—H26 | 119.9 |
C6—C14—H14B | 109.5 | C25—C26—C27 | 120.2 (3) |
C6—C14—H14C | 109.5 | C27—C26—H26 | 119.9 |
H14A—C14—H14B | 109.5 | C26—C27—H27 | 120.3 |
H14A—C14—H14C | 109.5 | C28—C27—C26 | 119.4 (3) |
H14B—C14—H14C | 109.5 | C28—C27—H27 | 120.3 |
C9—C15—H15A | 109.5 | C27—C28—H28 | 119.7 |
C9—C15—H15B | 109.5 | C27—C28—C29 | 120.5 (3) |
C9—C15—H15C | 109.5 | C29—C28—H28 | 119.7 |
H15A—C15—H15B | 109.5 | C24—C29—H29 | 119.8 |
H15A—C15—H15C | 109.5 | C28—C29—C24 | 120.5 (3) |
H15B—C15—H15C | 109.5 | C28—C29—H29 | 119.8 |
C1A—O1A—O2A | 111.33 (17) | C21A—O21A—H21A | 116 (2) |
C3A—O2A—O1A | 108.75 (16) | O21A—C21A—C22A | 111.6 (2) |
C2A—O3A—C3A | 113.09 (19) | O22A—C21A—O21A | 123.5 (3) |
C2A—N11A—H11A | 115 (2) | O22A—C21A—C22A | 124.9 (3) |
C10A—N11A—H11A | 117.7 (19) | C21A—C22A—H22A | 118.8 |
C10A—N11A—C2A | 127.8 (2) | C23A—C22A—C21A | 122.5 (2) |
O1A—C1A—C2A | 111.0 (2) | C23A—C22A—H22A | 118.8 |
O1A—C1A—C11A | 106.24 (18) | C22A—C23A—H23A | 117.5 |
O1A—C1A—C12A | 103.84 (19) | C22A—C23A—C24A | 125.1 (2) |
C2A—C1A—C11A | 111.1 (2) | C24A—C23A—H23A | 117.5 |
C2A—C1A—C12A | 111.35 (19) | C25A—C24A—C23A | 122.2 (3) |
C12A—C1A—C11A | 113.0 (2) | C29A—C24A—C23A | 119.5 (2) |
O3A—C2A—N11A | 107.88 (19) | C29A—C24A—C25A | 118.2 (3) |
O3A—C2A—C1A | 114.55 (18) | C24A—C25A—H25A | 119.5 |
O3A—C2A—H2A | 107.3 | C26A—C25A—C24A | 121.1 (3) |
N11A—C2A—C1A | 112.2 (2) | C26A—C25A—H25A | 119.5 |
N11A—C2A—H2A | 107.3 | C25A—C26A—H26A | 119.9 |
C1A—C2A—H2A | 107.3 | C25A—C26A—C27A | 120.3 (3) |
O2A—C3A—O3A | 108.09 (19) | C27A—C26A—H26A | 119.9 |
O2A—C3A—C4A | 112.7 (2) | C26A—C27A—H27A | 120.2 |
O2A—C3A—C13A | 104.8 (2) | C28A—C27A—C26A | 119.5 (3) |
O3A—C3A—C4A | 109.4 (2) | C28A—C27A—H27A | 120.2 |
O3A—C3A—C13A | 107.5 (2) | C27A—C28A—H28A | 119.7 |
C13A—C3A—C4A | 114.0 (2) | C27A—C28A—C29A | 120.5 (3) |
C3A—C4A—H4AA | 108.6 | C29A—C28A—H28A | 119.7 |
C3A—C4A—H4AB | 108.6 | C24A—C29A—H29A | 119.8 |
H4AA—C4A—H4AB | 107.5 | C28A—C29A—C24A | 120.3 (3) |
C5A—C4A—C3A | 114.8 (2) | C28A—C29A—H29A | 119.8 |
| | | |
O1—O2—C3—O3 | −75.1 (2) | O3A—C3A—C4A—C5A | 26.2 (3) |
O1—O2—C3—C4 | 46.6 (2) | C1A—O1A—O2A—C3A | 46.3 (2) |
O1—O2—C3—C13 | 170.81 (17) | C2A—O3A—C3A—O2A | 35.7 (2) |
O1—C1—C2—O3 | −52.4 (3) | C2A—O3A—C3A—C4A | −87.5 (2) |
O1—C1—C2—N11 | 71.7 (2) | C2A—O3A—C3A—C13A | 148.2 (2) |
O1—C1—C11—C5 | 68.4 (2) | C2A—N11A—C10A—O10A | 178.8 (2) |
O1—C1—C11—C6 | −165.09 (18) | C2A—N11A—C10A—C9A | −4.2 (4) |
O1—C1—C12—C8 | 170.72 (18) | C2A—C1A—C11A—C5A | −50.8 (3) |
O1—C1—C12—C9 | −61.1 (2) | C2A—C1A—C11A—C6A | 76.0 (3) |
O2—O1—C1—C2 | 14.0 (2) | C2A—C1A—C12A—C8A | −70.7 (2) |
O2—O1—C1—C11 | −107.65 (19) | C2A—C1A—C12A—C9A | 57.3 (2) |
O2—O1—C1—C12 | 133.08 (17) | C3A—O3A—C2A—N11A | −100.5 (2) |
O2—C3—C4—C5 | −95.7 (3) | C3A—O3A—C2A—C1A | 25.3 (3) |
O3—C3—C4—C5 | 24.8 (3) | C3A—C4A—C5A—C11A | 57.1 (3) |
C1—O1—O2—C3 | 46.7 (2) | C4A—C5A—C11A—C1A | −37.5 (3) |
C2—O3—C3—O2 | 35.4 (3) | C4A—C5A—C11A—C6A | −164.8 (2) |
C2—O3—C3—C4 | −87.7 (2) | C6A—C7A—C8A—C12A | 57.8 (3) |
C2—O3—C3—C13 | 147.9 (2) | C7A—C6A—C11A—C1A | 47.8 (3) |
C2—N11—C10—O10 | 174.9 (2) | C7A—C6A—C11A—C5A | 175.2 (2) |
C2—N11—C10—C9 | −8.5 (4) | C7A—C8A—C12A—C1A | −57.8 (3) |
C2—C1—C11—C5 | −53.0 (3) | C7A—C8A—C12A—C9A | 176.3 (2) |
C2—C1—C11—C6 | 73.5 (2) | C10A—N11A—C2A—O3A | 144.2 (2) |
C2—C1—C12—C8 | −70.0 (3) | C10A—N11A—C2A—C1A | 17.2 (3) |
C2—C1—C12—C9 | 58.2 (3) | C10A—C9A—C12A—C1A | −44.1 (3) |
C3—O3—C2—N11 | −99.8 (2) | C10A—C9A—C12A—C8A | 81.7 (3) |
C3—O3—C2—C1 | 26.3 (3) | C11A—C1A—C2A—O3A | 66.6 (2) |
C3—C4—C5—C11 | 57.2 (3) | C11A—C1A—C2A—N11A | −169.95 (19) |
C4—C5—C11—C1 | −36.1 (3) | C11A—C1A—C12A—C8A | 55.1 (3) |
C4—C5—C11—C6 | −163.4 (2) | C11A—C1A—C12A—C9A | −176.89 (19) |
C6—C7—C8—C12 | 57.0 (3) | C11A—C6A—C7A—C8A | −52.7 (3) |
C7—C6—C11—C1 | 49.3 (3) | C12A—C1A—C2A—O3A | −166.54 (19) |
C7—C6—C11—C5 | 176.62 (19) | C12A—C1A—C2A—N11A | −43.1 (3) |
C7—C8—C12—C1 | −57.2 (2) | C12A—C1A—C11A—C5A | −176.75 (19) |
C7—C8—C12—C9 | 177.2 (2) | C12A—C1A—C11A—C6A | −50.0 (3) |
C10—N11—C2—O3 | 145.9 (2) | C12A—C9A—C10A—O10A | −165.2 (2) |
C10—N11—C2—C1 | 19.4 (3) | C12A—C9A—C10A—N11A | 17.8 (3) |
C10—C9—C12—C1 | −47.0 (3) | C13A—C3A—C4A—C5A | 146.5 (2) |
C10—C9—C12—C8 | 78.9 (3) | C14A—C6A—C7A—C8A | −175.7 (2) |
C11—C1—C2—O3 | 66.7 (3) | C14A—C6A—C11A—C1A | 171.0 (2) |
C11—C1—C2—N11 | −169.17 (18) | C14A—C6A—C11A—C5A | −61.7 (3) |
C11—C1—C12—C8 | 55.1 (2) | C15A—C9A—C10A—O10A | −35.1 (3) |
C11—C1—C12—C9 | −176.72 (19) | C15A—C9A—C10A—N11A | 147.9 (2) |
C11—C6—C7—C8 | −52.7 (3) | C15A—C9A—C12A—C1A | −172.6 (2) |
C12—C1—C2—O3 | −167.5 (2) | C15A—C9A—C12A—C8A | −46.8 (3) |
C12—C1—C2—N11 | −43.4 (3) | O21—C21—C22—C23 | −177.7 (3) |
C12—C1—C11—C5 | −177.76 (19) | O22—C21—C22—C23 | 0.0 (5) |
C12—C1—C11—C6 | −51.3 (3) | C21—C22—C23—C24 | 173.5 (2) |
C12—C9—C10—O10 | −161.0 (2) | C22—C23—C24—C25 | 20.3 (4) |
C12—C9—C10—N11 | 22.3 (3) | C22—C23—C24—C29 | −156.2 (3) |
C13—C3—C4—C5 | 145.4 (2) | C23—C24—C25—C26 | −174.5 (3) |
C14—C6—C7—C8 | −175.8 (2) | C23—C24—C29—C28 | 174.8 (2) |
C14—C6—C11—C1 | 172.5 (2) | C24—C25—C26—C27 | −0.6 (4) |
C14—C6—C11—C5 | −60.2 (3) | C25—C24—C29—C28 | −1.8 (4) |
C15—C9—C10—O10 | −32.0 (3) | C25—C26—C27—C28 | −1.2 (4) |
C15—C9—C10—N11 | 151.3 (2) | C26—C27—C28—C29 | 1.4 (4) |
C15—C9—C12—C1 | −174.8 (2) | C27—C28—C29—C24 | 0.1 (4) |
C15—C9—C12—C8 | −48.9 (3) | C29—C24—C25—C26 | 2.1 (4) |
O1A—O2A—C3A—O3A | −74.7 (2) | O21A—C21A—C22A—C23A | −175.5 (3) |
O1A—O2A—C3A—C4A | 46.4 (2) | O22A—C21A—C22A—C23A | 2.8 (4) |
O1A—O2A—C3A—C13A | 170.94 (16) | C21A—C22A—C23A—C24A | 174.2 (2) |
O1A—C1A—C2A—O3A | −51.4 (3) | C22A—C23A—C24A—C25A | 22.8 (4) |
O1A—C1A—C2A—N11A | 72.1 (2) | C22A—C23A—C24A—C29A | −153.7 (3) |
O1A—C1A—C11A—C5A | 70.0 (3) | C23A—C24A—C25A—C26A | −173.8 (3) |
O1A—C1A—C11A—C6A | −163.2 (2) | C23A—C24A—C29A—C28A | 173.8 (3) |
O1A—C1A—C12A—C8A | 169.77 (19) | C24A—C25A—C26A—C27A | −0.6 (5) |
O1A—C1A—C12A—C9A | −62.2 (2) | C25A—C24A—C29A—C28A | −2.9 (4) |
O2A—O1A—C1A—C2A | 13.6 (2) | C25A—C26A—C27A—C28A | −1.5 (5) |
O2A—O1A—C1A—C11A | −107.2 (2) | C26A—C27A—C28A—C29A | 1.4 (4) |
O2A—O1A—C1A—C12A | 133.40 (17) | C27A—C28A—C29A—C24A | 0.9 (4) |
O2A—C3A—C4A—C5A | −94.2 (3) | C29A—C24A—C25A—C26A | 2.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O22 | 0.90 (3) | 2.13 (3) | 3.019 (3) | 169 (3) |
N11A—H11A···O22A | 0.90 (3) | 2.12 (3) | 3.009 (3) | 169 (3) |
O21—H21···O10 | 0.93 (4) | 1.66 (4) | 2.574 (3) | 167 (3) |
O21A—H21A···O10A | 0.98 (4) | 1.61 (4) | 2.576 (3) | 166 (4) |
1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0
4,13.0
8,13]hexadecan-10-one–
cis-butenedioic acid (1/1) (madiha29cult)
top
Crystal data top
C15H23NO4·C4H4O4 | Dx = 1.339 Mg m−3 |
Mr = 397.41 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 8948 reflections |
a = 9.62162 (12) Å | θ = 4.5–75.6° |
b = 10.40235 (11) Å | µ = 0.88 mm−1 |
c = 19.6935 (2) Å | T = 100 K |
V = 1971.08 (4) Å3 | Block, colourless |
Z = 4 | 0.4 × 0.4 × 0.35 mm |
F(000) = 848 | |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Atlas detector | 3504 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 3466 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.019 |
Detector resolution: 10.3577 pixels mm-1 | θmax = 67.5°, θmin = 5.1° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −12→12 |
Tmin = 0.716, Tmax = 1.000 | l = −23→20 |
11105 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.022 | w = 1/[σ2(Fo2) + (0.032P)2 + 0.2852P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.056 | (Δ/σ)max = 0.001 |
S = 1.01 | Δρmax = 0.18 e Å−3 |
3504 reflections | Δρmin = −0.14 e Å−3 |
268 parameters | Absolute structure: Flack x determined using 1483 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
0 restraints | Absolute structure parameter: −0.10 (4) |
Primary atom site location: structure-invariant direct methods | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.13170 (10) | 0.26302 (10) | 0.57995 (5) | 0.0174 (2) | |
O2 | 0.12539 (10) | 0.13681 (10) | 0.54588 (5) | 0.0179 (2) | |
O3 | 0.36214 (10) | 0.11255 (10) | 0.53420 (5) | 0.0166 (2) | |
O10 | 0.25079 (11) | 0.40482 (10) | 0.37164 (5) | 0.0192 (2) | |
N11 | 0.32147 (12) | 0.27619 (12) | 0.45656 (6) | 0.0156 (2) | |
H11 | 0.351 (2) | 0.224 (2) | 0.4254 (10) | 0.024 (5)* | |
C1 | 0.27190 (15) | 0.31804 (14) | 0.57780 (7) | 0.0156 (3) | |
C2 | 0.36156 (15) | 0.24771 (13) | 0.52617 (7) | 0.0147 (3) | |
H2 | 0.4593 | 0.2783 | 0.5323 | 0.018* | |
C3 | 0.24132 (15) | 0.06274 (14) | 0.56756 (8) | 0.0182 (3) | |
C4 | 0.25854 (17) | 0.06638 (15) | 0.64479 (8) | 0.0223 (3) | |
H4A | 0.1671 | 0.0849 | 0.6656 | 0.027* | |
H4B | 0.2882 | −0.0197 | 0.6606 | 0.027* | |
C5 | 0.36331 (17) | 0.16579 (16) | 0.66992 (8) | 0.0228 (3) | |
H5A | 0.4562 | 0.1421 | 0.6523 | 0.027* | |
H5B | 0.3675 | 0.1607 | 0.7201 | 0.027* | |
C6 | 0.46439 (17) | 0.38974 (17) | 0.65924 (8) | 0.0263 (4) | |
H6 | 0.5390 | 0.3542 | 0.6293 | 0.032* | |
C7 | 0.43671 (19) | 0.52849 (17) | 0.63734 (9) | 0.0296 (4) | |
H7A | 0.3678 | 0.5674 | 0.6685 | 0.035* | |
H7B | 0.5239 | 0.5785 | 0.6410 | 0.035* | |
C8 | 0.38249 (16) | 0.53724 (15) | 0.56482 (9) | 0.0231 (3) | |
H8A | 0.4539 | 0.5044 | 0.5331 | 0.028* | |
H8B | 0.3640 | 0.6283 | 0.5533 | 0.028* | |
C9 | 0.18497 (15) | 0.46594 (14) | 0.48504 (8) | 0.0168 (3) | |
H9 | 0.0892 | 0.4296 | 0.4895 | 0.020* | |
C10 | 0.25789 (14) | 0.38138 (13) | 0.43396 (7) | 0.0148 (3) | |
C11 | 0.33353 (16) | 0.30612 (15) | 0.64984 (7) | 0.0202 (3) | |
H11A | 0.2618 | 0.3393 | 0.6822 | 0.024* | |
C12 | 0.24835 (15) | 0.45867 (14) | 0.55666 (7) | 0.0175 (3) | |
H12 | 0.1785 | 0.4957 | 0.5888 | 0.021* | |
C13 | 0.21698 (17) | −0.07039 (14) | 0.53893 (9) | 0.0238 (3) | |
H13A | 0.1929 | −0.0638 | 0.4907 | 0.036* | |
H13B | 0.1406 | −0.1117 | 0.5636 | 0.036* | |
H13C | 0.3017 | −0.1219 | 0.5440 | 0.036* | |
C14 | 0.5169 (2) | 0.3851 (2) | 0.73242 (9) | 0.0398 (5) | |
H14A | 0.4421 | 0.4113 | 0.7633 | 0.060* | |
H14B | 0.5959 | 0.4437 | 0.7375 | 0.060* | |
H14C | 0.5462 | 0.2973 | 0.7434 | 0.060* | |
C15 | 0.16500 (18) | 0.60305 (15) | 0.45888 (8) | 0.0245 (3) | |
H15A | 0.2560 | 0.6424 | 0.4506 | 0.037* | |
H15B | 0.1144 | 0.6536 | 0.4928 | 0.037* | |
H15C | 0.1118 | 0.6011 | 0.4165 | 0.037* | |
O21 | 0.40673 (12) | 0.29370 (10) | 0.28549 (6) | 0.0214 (2) | |
H21 | 0.347 (3) | 0.327 (3) | 0.3188 (14) | 0.055 (7)* | |
O22 | 0.36344 (12) | 0.10985 (10) | 0.33941 (5) | 0.0226 (2) | |
O23 | 0.66564 (12) | 0.36037 (11) | 0.18037 (6) | 0.0251 (2) | |
H23 | 0.650 (3) | 0.443 (2) | 0.1681 (12) | 0.045 (6)* | |
O24 | 0.46072 (14) | 0.31992 (12) | 0.13105 (7) | 0.0345 (3) | |
C21 | 0.42193 (16) | 0.17039 (14) | 0.29387 (7) | 0.0174 (3) | |
C22 | 0.51583 (16) | 0.10315 (14) | 0.24596 (8) | 0.0190 (3) | |
H22 | 0.5347 | 0.0153 | 0.2553 | 0.023* | |
C23 | 0.57634 (16) | 0.15295 (14) | 0.19137 (7) | 0.0191 (3) | |
H23A | 0.6371 | 0.0982 | 0.1667 | 0.023* | |
C24 | 0.55830 (17) | 0.28680 (15) | 0.16494 (7) | 0.0191 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0117 (5) | 0.0174 (5) | 0.0230 (5) | −0.0015 (4) | 0.0026 (4) | −0.0019 (4) |
O2 | 0.0136 (5) | 0.0152 (5) | 0.0248 (5) | −0.0008 (4) | −0.0037 (4) | 0.0004 (4) |
O3 | 0.0133 (5) | 0.0161 (5) | 0.0203 (5) | 0.0012 (4) | 0.0016 (4) | 0.0016 (4) |
O10 | 0.0224 (6) | 0.0164 (5) | 0.0189 (5) | 0.0015 (4) | 0.0005 (4) | 0.0015 (4) |
N11 | 0.0155 (6) | 0.0145 (5) | 0.0169 (6) | 0.0017 (5) | 0.0018 (5) | −0.0024 (5) |
C1 | 0.0096 (6) | 0.0199 (7) | 0.0173 (7) | −0.0017 (5) | 0.0018 (5) | −0.0018 (6) |
C2 | 0.0118 (6) | 0.0163 (7) | 0.0158 (6) | 0.0000 (6) | 0.0003 (5) | −0.0011 (5) |
C3 | 0.0116 (7) | 0.0189 (7) | 0.0241 (7) | 0.0000 (6) | −0.0014 (6) | 0.0063 (6) |
C4 | 0.0183 (8) | 0.0263 (8) | 0.0223 (7) | −0.0020 (6) | 0.0001 (6) | 0.0080 (6) |
C5 | 0.0198 (7) | 0.0310 (8) | 0.0177 (6) | −0.0011 (7) | −0.0026 (6) | 0.0016 (6) |
C6 | 0.0217 (8) | 0.0323 (9) | 0.0250 (8) | −0.0039 (7) | −0.0048 (6) | −0.0087 (7) |
C7 | 0.0284 (9) | 0.0261 (8) | 0.0341 (9) | −0.0059 (7) | −0.0039 (7) | −0.0125 (7) |
C8 | 0.0195 (7) | 0.0185 (7) | 0.0313 (8) | −0.0042 (6) | 0.0024 (7) | −0.0055 (6) |
C9 | 0.0133 (7) | 0.0155 (7) | 0.0217 (7) | 0.0014 (6) | 0.0032 (6) | 0.0003 (6) |
C10 | 0.0112 (6) | 0.0133 (6) | 0.0199 (7) | −0.0033 (5) | 0.0012 (5) | −0.0002 (5) |
C11 | 0.0174 (7) | 0.0267 (8) | 0.0165 (7) | −0.0012 (6) | 0.0013 (6) | −0.0037 (6) |
C12 | 0.0150 (7) | 0.0165 (7) | 0.0210 (7) | 0.0003 (6) | 0.0033 (6) | −0.0038 (5) |
C13 | 0.0217 (8) | 0.0170 (7) | 0.0328 (9) | −0.0003 (6) | −0.0051 (7) | 0.0043 (6) |
C14 | 0.0399 (11) | 0.0489 (12) | 0.0308 (9) | −0.0073 (10) | −0.0131 (8) | −0.0106 (9) |
C15 | 0.0300 (8) | 0.0169 (7) | 0.0267 (7) | 0.0052 (6) | 0.0072 (7) | −0.0003 (6) |
O21 | 0.0283 (6) | 0.0132 (5) | 0.0228 (5) | 0.0028 (4) | 0.0055 (4) | 0.0004 (4) |
O22 | 0.0318 (6) | 0.0145 (5) | 0.0216 (5) | −0.0010 (5) | 0.0043 (4) | −0.0010 (4) |
O23 | 0.0264 (6) | 0.0154 (5) | 0.0336 (6) | 0.0006 (5) | −0.0014 (5) | 0.0023 (5) |
O24 | 0.0421 (8) | 0.0253 (6) | 0.0361 (6) | 0.0010 (6) | −0.0190 (6) | 0.0040 (5) |
C21 | 0.0195 (7) | 0.0154 (7) | 0.0174 (7) | −0.0011 (6) | −0.0038 (6) | −0.0014 (5) |
C22 | 0.0230 (8) | 0.0125 (7) | 0.0215 (7) | 0.0017 (6) | −0.0024 (6) | −0.0024 (6) |
C23 | 0.0213 (7) | 0.0152 (7) | 0.0208 (7) | 0.0014 (6) | −0.0014 (6) | −0.0046 (6) |
C24 | 0.0263 (8) | 0.0175 (7) | 0.0133 (6) | 0.0019 (6) | 0.0012 (6) | −0.0026 (5) |
Geometric parameters (Å, º) top
O1—O2 | 1.4757 (14) | C8—H8B | 0.9900 |
O1—C1 | 1.4660 (17) | C8—C12 | 1.536 (2) |
O2—C3 | 1.4213 (17) | C9—H9 | 1.0000 |
O3—C2 | 1.4149 (17) | C9—C10 | 1.5091 (19) |
O3—C3 | 1.4323 (17) | C9—C12 | 1.538 (2) |
O10—C10 | 1.2532 (18) | C9—C15 | 1.529 (2) |
N11—H11 | 0.87 (2) | C11—H11A | 1.0000 |
N11—C2 | 1.4546 (18) | C12—H12 | 1.0000 |
N11—C10 | 1.3303 (19) | C13—H13A | 0.9800 |
C1—C2 | 1.5209 (19) | C13—H13B | 0.9800 |
C1—C11 | 1.543 (2) | C13—H13C | 0.9800 |
C1—C12 | 1.538 (2) | C14—H14A | 0.9800 |
C2—H2 | 1.0000 | C14—H14B | 0.9800 |
C3—C4 | 1.530 (2) | C14—H14C | 0.9800 |
C3—C13 | 1.513 (2) | C15—H15A | 0.9800 |
C4—H4A | 0.9900 | C15—H15B | 0.9800 |
C4—H4B | 0.9900 | C15—H15C | 0.9800 |
C4—C5 | 1.527 (2) | O21—H21 | 0.94 (3) |
C5—H5A | 0.9900 | O21—C21 | 1.3015 (19) |
C5—H5B | 0.9900 | O22—C21 | 1.2320 (19) |
C5—C11 | 1.539 (2) | O23—H23 | 0.90 (2) |
C6—H6 | 1.0000 | O23—C24 | 1.321 (2) |
C6—C7 | 1.530 (2) | O24—C24 | 1.202 (2) |
C6—C11 | 1.542 (2) | C21—C22 | 1.482 (2) |
C6—C14 | 1.528 (2) | C22—H22 | 0.9500 |
C7—H7A | 0.9900 | C22—C23 | 1.328 (2) |
C7—H7B | 0.9900 | C23—H23A | 0.9500 |
C7—C8 | 1.523 (2) | C23—C24 | 1.497 (2) |
C8—H8A | 0.9900 | | |
| | | |
C1—O1—O2 | 111.84 (9) | C10—C9—H9 | 105.5 |
C3—O2—O1 | 108.27 (10) | C10—C9—C12 | 113.46 (12) |
C2—O3—C3 | 114.05 (10) | C10—C9—C15 | 112.19 (12) |
C2—N11—H11 | 116.8 (13) | C12—C9—H9 | 105.5 |
C10—N11—H11 | 115.5 (13) | C15—C9—H9 | 105.5 |
C10—N11—C2 | 127.20 (12) | C15—C9—C12 | 113.86 (12) |
O1—C1—C2 | 110.70 (11) | O10—C10—N11 | 120.84 (13) |
O1—C1—C11 | 107.20 (11) | O10—C10—C9 | 120.93 (12) |
O1—C1—C12 | 104.10 (11) | N11—C10—C9 | 118.06 (12) |
C2—C1—C11 | 110.99 (12) | C1—C11—H11A | 107.0 |
C2—C1—C12 | 111.11 (11) | C5—C11—C1 | 112.58 (12) |
C12—C1—C11 | 112.47 (12) | C5—C11—C6 | 110.63 (13) |
O3—C2—N11 | 107.98 (11) | C5—C11—H11A | 107.0 |
O3—C2—C1 | 113.92 (11) | C6—C11—C1 | 112.27 (12) |
O3—C2—H2 | 107.4 | C6—C11—H11A | 107.0 |
N11—C2—C1 | 112.44 (12) | C1—C12—C9 | 110.69 (11) |
N11—C2—H2 | 107.4 | C1—C12—H12 | 107.1 |
C1—C2—H2 | 107.4 | C8—C12—C1 | 110.73 (12) |
O2—C3—O3 | 107.64 (11) | C8—C12—C9 | 113.76 (13) |
O2—C3—C4 | 111.72 (12) | C8—C12—H12 | 107.1 |
O2—C3—C13 | 105.23 (12) | C9—C12—H12 | 107.1 |
O3—C3—C4 | 111.04 (12) | C3—C13—H13A | 109.5 |
O3—C3—C13 | 106.61 (12) | C3—C13—H13B | 109.5 |
C13—C3—C4 | 114.18 (13) | C3—C13—H13C | 109.5 |
C3—C4—H4A | 108.7 | H13A—C13—H13B | 109.5 |
C3—C4—H4B | 108.7 | H13A—C13—H13C | 109.5 |
H4A—C4—H4B | 107.6 | H13B—C13—H13C | 109.5 |
C5—C4—C3 | 114.23 (13) | C6—C14—H14A | 109.5 |
C5—C4—H4A | 108.7 | C6—C14—H14B | 109.5 |
C5—C4—H4B | 108.7 | C6—C14—H14C | 109.5 |
C4—C5—H5A | 108.3 | H14A—C14—H14B | 109.5 |
C4—C5—H5B | 108.3 | H14A—C14—H14C | 109.5 |
C4—C5—C11 | 115.87 (13) | H14B—C14—H14C | 109.5 |
H5A—C5—H5B | 107.4 | C9—C15—H15A | 109.5 |
C11—C5—H5A | 108.3 | C9—C15—H15B | 109.5 |
C11—C5—H5B | 108.3 | C9—C15—H15C | 109.5 |
C7—C6—H6 | 107.9 | H15A—C15—H15B | 109.5 |
C7—C6—C11 | 110.88 (14) | H15A—C15—H15C | 109.5 |
C11—C6—H6 | 107.9 | H15B—C15—H15C | 109.5 |
C14—C6—H6 | 107.9 | C21—O21—H21 | 110.2 (16) |
C14—C6—C7 | 110.69 (15) | C24—O23—H23 | 111.1 (16) |
C14—C6—C11 | 111.42 (14) | O21—C21—C22 | 116.94 (13) |
C6—C7—H7A | 109.1 | O22—C21—O21 | 123.01 (14) |
C6—C7—H7B | 109.1 | O22—C21—C22 | 120.05 (14) |
H7A—C7—H7B | 107.9 | C21—C22—H22 | 116.6 |
C8—C7—C6 | 112.35 (13) | C23—C22—C21 | 126.77 (14) |
C8—C7—H7A | 109.1 | C23—C22—H22 | 116.6 |
C8—C7—H7B | 109.1 | C22—C23—H23A | 116.8 |
C7—C8—H8A | 109.5 | C22—C23—C24 | 126.43 (14) |
C7—C8—H8B | 109.5 | C24—C23—H23A | 116.8 |
C7—C8—C12 | 110.74 (14) | O23—C24—C23 | 111.61 (13) |
H8A—C8—H8B | 108.1 | O24—C24—O23 | 124.91 (14) |
C12—C8—H8A | 109.5 | O24—C24—C23 | 123.38 (14) |
C12—C8—H8B | 109.5 | | |
| | | |
O1—O2—C3—O3 | −74.51 (13) | C7—C6—C11—C5 | 178.29 (13) |
O1—O2—C3—C4 | 47.64 (14) | C7—C8—C12—C1 | −56.21 (16) |
O1—O2—C3—C13 | 172.07 (11) | C7—C8—C12—C9 | 178.39 (13) |
O1—C1—C2—O3 | −51.62 (15) | C10—N11—C2—O3 | 152.17 (13) |
O1—C1—C2—N11 | 71.65 (14) | C10—N11—C2—C1 | 25.64 (19) |
O1—C1—C11—C5 | 68.73 (15) | C10—C9—C12—C1 | −47.19 (16) |
O1—C1—C11—C6 | −165.63 (12) | C10—C9—C12—C8 | 78.24 (15) |
O1—C1—C12—C8 | 169.41 (11) | C11—C1—C2—O3 | 67.29 (15) |
O1—C1—C12—C9 | −63.48 (14) | C11—C1—C2—N11 | −169.43 (12) |
O2—O1—C1—C2 | 14.64 (14) | C11—C1—C12—C8 | 53.70 (15) |
O2—O1—C1—C11 | −106.54 (11) | C11—C1—C12—C9 | −179.19 (12) |
O2—O1—C1—C12 | 134.10 (10) | C11—C6—C7—C8 | −55.12 (18) |
O2—C3—C4—C5 | −96.54 (15) | C12—C1—C2—O3 | −166.77 (11) |
O3—C3—C4—C5 | 23.64 (18) | C12—C1—C2—N11 | −43.50 (15) |
C1—O1—O2—C3 | 45.45 (13) | C12—C1—C11—C5 | −177.44 (12) |
C2—O3—C3—O2 | 36.57 (15) | C12—C1—C11—C6 | −51.81 (16) |
C2—O3—C3—C4 | −86.00 (14) | C12—C9—C10—O10 | −157.01 (13) |
C2—O3—C3—C13 | 149.06 (11) | C12—C9—C10—N11 | 27.73 (18) |
C2—N11—C10—O10 | 167.29 (13) | C13—C3—C4—C5 | 144.20 (14) |
C2—N11—C10—C9 | −17.5 (2) | C14—C6—C7—C8 | −179.31 (15) |
C2—C1—C11—C5 | −52.27 (16) | C14—C6—C11—C1 | 175.37 (14) |
C2—C1—C11—C6 | 73.37 (16) | C14—C6—C11—C5 | −57.94 (18) |
C2—C1—C12—C8 | −71.41 (15) | C15—C9—C10—O10 | −26.22 (19) |
C2—C1—C12—C9 | 55.71 (15) | C15—C9—C10—N11 | 158.53 (13) |
C3—O3—C2—N11 | −100.94 (13) | C15—C9—C12—C1 | −177.15 (12) |
C3—O3—C2—C1 | 24.72 (16) | C15—C9—C12—C8 | −51.72 (17) |
C3—C4—C5—C11 | 58.32 (18) | O21—C21—C22—C23 | −6.8 (2) |
C4—C5—C11—C1 | −36.84 (18) | O22—C21—C22—C23 | 173.89 (16) |
C4—C5—C11—C6 | −163.36 (13) | C21—C22—C23—C24 | −2.5 (3) |
C6—C7—C8—C12 | 57.80 (18) | C22—C23—C24—O23 | 102.65 (19) |
C7—C6—C11—C1 | 51.59 (17) | C22—C23—C24—O24 | −80.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O22 | 0.87 (2) | 2.07 (2) | 2.9118 (16) | 163.0 (19) |
O21—H21···O10 | 0.94 (3) | 1.61 (3) | 2.5428 (15) | 172 (3) |
O23—H23···O22i | 0.90 (2) | 1.75 (2) | 2.6392 (15) | 168 (2) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0
4,13.0
8,13]hexadecan-10-one–
cis-butenedioic acid (2/1) (madiha55cult)
top
Crystal data top
2C15H23NO4·C4H4O4 | Dx = 1.365 Mg m−3 |
Mr = 678.76 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 7193 reflections |
a = 9.7885 (1) Å | θ = 4.6–75.4° |
b = 9.9965 (1) Å | µ = 0.86 mm−1 |
c = 33.7661 (4) Å | T = 100 K |
V = 3304.04 (6) Å3 | Block, colourless |
Z = 4 | 0.2 × 0.2 × 0.1 mm |
F(000) = 1456 | |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Atlas detector | 5886 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 5726 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.021 |
Detector resolution: 10.3577 pixels mm-1 | θmax = 67.5°, θmin = 4.6° |
ω scans | h = −10→11 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −8→11 |
Tmin = 0.973, Tmax = 1.000 | l = −40→28 |
9569 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.040P)2 + 0.6791P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.21 e Å−3 |
5886 reflections | Δρmin = −0.18 e Å−3 |
455 parameters | Absolute structure: Flack x determined using 2414 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.02 (7) |
Primary atom site location: structure-invariant direct methods | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4239 (2) | 0.5209 (2) | 0.45667 (6) | 0.0152 (4) | |
N1 | 0.58735 (18) | 0.35610 (17) | 0.42840 (5) | 0.0168 (4) | |
H1 | 0.659 (3) | 0.339 (3) | 0.4132 (8) | 0.023 (6)* | |
O1 | 0.49755 (14) | 0.55528 (15) | 0.49297 (4) | 0.0181 (3) | |
C2 | 0.5224 (2) | 0.4865 (2) | 0.42312 (6) | 0.0147 (4) | |
H2 | 0.4673 | 0.4816 | 0.3982 | 0.018* | |
O2 | 0.64369 (14) | 0.57876 (15) | 0.48525 (4) | 0.0184 (3) | |
C3 | 0.6543 (2) | 0.6633 (2) | 0.45172 (6) | 0.0172 (4) | |
O3 | 0.62388 (14) | 0.58492 (14) | 0.41716 (4) | 0.0151 (3) | |
C4 | 0.5584 (2) | 0.7841 (2) | 0.45467 (6) | 0.0196 (4) | |
H4A | 0.5412 | 0.8033 | 0.4830 | 0.024* | |
H4B | 0.6049 | 0.8630 | 0.4432 | 0.024* | |
C5 | 0.4210 (2) | 0.7655 (2) | 0.43375 (6) | 0.0196 (4) | |
H5A | 0.4383 | 0.7606 | 0.4049 | 0.024* | |
H5B | 0.3652 | 0.8465 | 0.4386 | 0.024* | |
C6 | 0.2285 (2) | 0.6074 (2) | 0.41371 (6) | 0.0189 (4) | |
H6 | 0.2782 | 0.5820 | 0.3889 | 0.023* | |
C7 | 0.1432 (2) | 0.4876 (2) | 0.42687 (7) | 0.0226 (5) | |
H7A | 0.0896 | 0.5124 | 0.4506 | 0.027* | |
H7B | 0.0782 | 0.4637 | 0.4056 | 0.027* | |
C8 | 0.2318 (2) | 0.3664 (2) | 0.43645 (7) | 0.0205 (4) | |
H8A | 0.2798 | 0.3367 | 0.4122 | 0.025* | |
H8B | 0.1731 | 0.2920 | 0.4456 | 0.025* | |
C9 | 0.4291 (2) | 0.2821 (2) | 0.48027 (6) | 0.0207 (4) | |
H9 | 0.4758 | 0.3093 | 0.5054 | 0.025* | |
C10 | 0.5412 (2) | 0.2546 (2) | 0.45075 (7) | 0.0192 (4) | |
O10 | 0.59364 (17) | 0.14148 (15) | 0.44918 (6) | 0.0297 (4) | |
C11 | 0.3358 (2) | 0.6430 (2) | 0.44559 (6) | 0.0171 (4) | |
H11 | 0.2839 | 0.6685 | 0.4700 | 0.020* | |
C12 | 0.3369 (2) | 0.4000 (2) | 0.46856 (6) | 0.0176 (4) | |
H12 | 0.2845 | 0.4263 | 0.4928 | 0.021* | |
C13 | 0.8037 (2) | 0.6988 (2) | 0.44857 (7) | 0.0210 (4) | |
H13A | 0.8587 | 0.6170 | 0.4495 | 0.031* | |
H13B | 0.8291 | 0.7574 | 0.4707 | 0.031* | |
H13C | 0.8203 | 0.7453 | 0.4235 | 0.031* | |
C14 | 0.1366 (2) | 0.7271 (2) | 0.40429 (7) | 0.0260 (5) | |
H14A | 0.0974 | 0.7621 | 0.4289 | 0.039* | |
H14B | 0.0628 | 0.6987 | 0.3866 | 0.039* | |
H14C | 0.1907 | 0.7971 | 0.3914 | 0.039* | |
C15 | 0.3503 (2) | 0.1538 (2) | 0.48994 (8) | 0.0294 (5) | |
H15A | 0.2783 | 0.1738 | 0.5092 | 0.044* | |
H15B | 0.4131 | 0.0874 | 0.5011 | 0.044* | |
H15C | 0.3091 | 0.1182 | 0.4657 | 0.044* | |
C1A | 0.7189 (2) | 0.6715 (2) | 0.29446 (6) | 0.0154 (4) | |
N1A | 0.89184 (18) | 0.51898 (18) | 0.32339 (5) | 0.0174 (4) | |
H1A | 0.907 (3) | 0.443 (3) | 0.3348 (8) | 0.027 (7)* | |
O1A | 0.69096 (15) | 0.59186 (14) | 0.25893 (4) | 0.0178 (3) | |
C2A | 0.7575 (2) | 0.5804 (2) | 0.32907 (6) | 0.0149 (4) | |
H2A | 0.7626 | 0.6373 | 0.3534 | 0.018* | |
O2A | 0.67404 (15) | 0.44902 (14) | 0.26854 (4) | 0.0184 (3) | |
C3A | 0.5861 (2) | 0.4382 (2) | 0.30168 (6) | 0.0171 (4) | |
O3A | 0.66195 (14) | 0.47756 (14) | 0.33643 (4) | 0.0155 (3) | |
C4A | 0.4578 (2) | 0.5243 (2) | 0.29709 (6) | 0.0196 (4) | |
H4AA | 0.3794 | 0.4760 | 0.3089 | 0.023* | |
H4AB | 0.4386 | 0.5361 | 0.2685 | 0.023* | |
C5A | 0.4683 (2) | 0.6625 (2) | 0.31641 (6) | 0.0193 (4) | |
H5AA | 0.4753 | 0.6499 | 0.3454 | 0.023* | |
H5AB | 0.3820 | 0.7112 | 0.3112 | 0.023* | |
C6A | 0.6120 (2) | 0.8667 (2) | 0.33295 (6) | 0.0196 (4) | |
H6A | 0.6333 | 0.8262 | 0.3593 | 0.024* | |
C7A | 0.7344 (2) | 0.9519 (2) | 0.32033 (7) | 0.0222 (4) | |
H7AA | 0.7122 | 0.9986 | 0.2953 | 0.027* | |
H7AB | 0.7518 | 1.0208 | 0.3408 | 0.027* | |
C8A | 0.8629 (2) | 0.8693 (2) | 0.31446 (6) | 0.0208 (4) | |
H8AA | 0.8888 | 0.8263 | 0.3398 | 0.025* | |
H8AB | 0.9389 | 0.9283 | 0.3061 | 0.025* | |
C9A | 0.9652 (2) | 0.6773 (2) | 0.27198 (6) | 0.0207 (4) | |
H9A | 0.9449 | 0.6376 | 0.2454 | 0.025* | |
C10A | 0.9912 (2) | 0.5600 (2) | 0.29921 (6) | 0.0187 (4) | |
O10A | 1.10277 (15) | 0.50020 (16) | 0.29724 (5) | 0.0264 (3) | |
C11A | 0.5873 (2) | 0.7514 (2) | 0.30313 (6) | 0.0173 (4) | |
H11A | 0.5590 | 0.7939 | 0.2776 | 0.021* | |
C12A | 0.8391 (2) | 0.7614 (2) | 0.28285 (6) | 0.0185 (4) | |
H12A | 0.8111 | 0.8094 | 0.2582 | 0.022* | |
C13A | 0.5593 (2) | 0.2902 (2) | 0.30643 (7) | 0.0220 (4) | |
H13D | 0.6459 | 0.2412 | 0.3048 | 0.033* | |
H13E | 0.4980 | 0.2598 | 0.2853 | 0.033* | |
H13F | 0.5168 | 0.2737 | 0.3322 | 0.033* | |
C14A | 0.4847 (2) | 0.9543 (2) | 0.33759 (7) | 0.0258 (5) | |
H14D | 0.4583 | 0.9903 | 0.3117 | 0.039* | |
H14E | 0.5047 | 1.0282 | 0.3558 | 0.039* | |
H14F | 0.4097 | 0.9004 | 0.3483 | 0.039* | |
C15A | 1.0957 (2) | 0.7599 (3) | 0.26655 (8) | 0.0313 (5) | |
H15D | 1.0776 | 0.8345 | 0.2485 | 0.047* | |
H15E | 1.1677 | 0.7030 | 0.2554 | 0.047* | |
H15F | 1.1254 | 0.7948 | 0.2923 | 0.047* | |
C21 | 0.9037 (2) | 0.1337 (2) | 0.41140 (7) | 0.0223 (5) | |
O21 | 0.81182 (17) | 0.04403 (16) | 0.42055 (5) | 0.0269 (4) | |
H21 | 0.732 (4) | 0.086 (3) | 0.4277 (10) | 0.043 (9)* | |
C22 | 1.0388 (2) | 0.0711 (2) | 0.40218 (7) | 0.0249 (5) | |
H22 | 1.0694 | 0.0006 | 0.4188 | 0.030* | |
O22 | 0.8829 (2) | 0.25272 (18) | 0.41105 (8) | 0.0525 (6) | |
C23 | 1.1185 (2) | 0.1070 (2) | 0.37251 (7) | 0.0260 (5) | |
H23A | 1.2037 | 0.0628 | 0.3692 | 0.031* | |
O23 | 1.18129 (17) | 0.29587 (18) | 0.33620 (5) | 0.0305 (4) | |
H23 | 1.149 (4) | 0.365 (4) | 0.3219 (10) | 0.050 (10)* | |
C24 | 1.0798 (2) | 0.2144 (2) | 0.34383 (7) | 0.0239 (5) | |
O24 | 0.9674 (2) | 0.2250 (2) | 0.32975 (7) | 0.0515 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0135 (9) | 0.0177 (10) | 0.0146 (9) | 0.0002 (8) | 0.0003 (7) | −0.0005 (7) |
N1 | 0.0141 (8) | 0.0145 (8) | 0.0218 (9) | 0.0010 (7) | 0.0042 (7) | −0.0001 (7) |
O1 | 0.0139 (7) | 0.0260 (8) | 0.0143 (6) | −0.0018 (6) | 0.0023 (5) | −0.0003 (6) |
C2 | 0.0129 (9) | 0.0150 (9) | 0.0161 (9) | −0.0014 (8) | 0.0007 (8) | 0.0008 (7) |
O2 | 0.0129 (7) | 0.0242 (7) | 0.0181 (7) | −0.0014 (6) | −0.0004 (6) | 0.0011 (6) |
C3 | 0.0187 (10) | 0.0186 (10) | 0.0143 (9) | −0.0015 (8) | −0.0005 (8) | −0.0017 (8) |
O3 | 0.0152 (7) | 0.0144 (7) | 0.0159 (6) | −0.0018 (5) | 0.0024 (5) | −0.0006 (5) |
C4 | 0.0195 (10) | 0.0161 (10) | 0.0233 (10) | −0.0034 (8) | 0.0035 (8) | −0.0024 (8) |
C5 | 0.0185 (10) | 0.0160 (10) | 0.0244 (10) | 0.0020 (8) | 0.0014 (9) | 0.0000 (8) |
C6 | 0.0149 (10) | 0.0196 (10) | 0.0222 (10) | 0.0014 (8) | −0.0004 (8) | 0.0024 (8) |
C7 | 0.0149 (10) | 0.0228 (11) | 0.0301 (11) | −0.0021 (9) | −0.0021 (9) | 0.0014 (9) |
C8 | 0.0154 (10) | 0.0188 (11) | 0.0273 (11) | −0.0037 (8) | 0.0001 (9) | 0.0020 (8) |
C9 | 0.0179 (10) | 0.0202 (11) | 0.0240 (10) | −0.0012 (9) | 0.0019 (9) | 0.0069 (8) |
C10 | 0.0147 (10) | 0.0160 (10) | 0.0269 (11) | −0.0009 (8) | −0.0008 (8) | 0.0023 (8) |
O10 | 0.0227 (8) | 0.0153 (7) | 0.0513 (10) | 0.0012 (7) | 0.0085 (8) | 0.0070 (7) |
C11 | 0.0145 (9) | 0.0173 (10) | 0.0194 (9) | 0.0015 (8) | 0.0029 (8) | −0.0005 (8) |
C12 | 0.0151 (9) | 0.0181 (10) | 0.0197 (9) | −0.0006 (8) | 0.0033 (8) | 0.0022 (8) |
C13 | 0.0164 (10) | 0.0230 (10) | 0.0234 (10) | −0.0024 (9) | 0.0010 (8) | −0.0025 (9) |
C14 | 0.0176 (11) | 0.0240 (12) | 0.0364 (13) | 0.0032 (9) | −0.0012 (9) | 0.0070 (9) |
C15 | 0.0234 (11) | 0.0227 (11) | 0.0421 (13) | 0.0011 (9) | 0.0077 (10) | 0.0138 (10) |
C1A | 0.0164 (9) | 0.0164 (10) | 0.0133 (9) | −0.0004 (8) | −0.0013 (7) | −0.0002 (8) |
N1A | 0.0154 (8) | 0.0165 (9) | 0.0205 (8) | 0.0008 (7) | −0.0011 (7) | 0.0044 (7) |
O1A | 0.0243 (8) | 0.0146 (7) | 0.0144 (6) | −0.0018 (6) | −0.0004 (6) | 0.0011 (5) |
C2A | 0.0132 (9) | 0.0159 (9) | 0.0156 (9) | −0.0022 (8) | 0.0005 (7) | 0.0000 (7) |
O2A | 0.0230 (7) | 0.0133 (7) | 0.0189 (7) | 0.0001 (6) | 0.0031 (6) | −0.0010 (5) |
C3A | 0.0170 (9) | 0.0180 (10) | 0.0164 (9) | −0.0024 (8) | −0.0001 (8) | −0.0013 (8) |
O3A | 0.0156 (7) | 0.0160 (7) | 0.0150 (6) | −0.0024 (6) | 0.0008 (6) | 0.0009 (5) |
C4A | 0.0154 (9) | 0.0187 (10) | 0.0247 (10) | −0.0017 (8) | −0.0010 (8) | 0.0007 (9) |
C5A | 0.0158 (10) | 0.0170 (10) | 0.0251 (10) | 0.0022 (8) | 0.0013 (8) | −0.0003 (8) |
C6A | 0.0257 (11) | 0.0148 (9) | 0.0183 (9) | 0.0023 (9) | −0.0005 (8) | 0.0006 (8) |
C7A | 0.0270 (11) | 0.0156 (10) | 0.0239 (10) | −0.0026 (9) | −0.0035 (9) | 0.0005 (8) |
C8A | 0.0210 (11) | 0.0171 (10) | 0.0243 (10) | −0.0052 (8) | −0.0036 (9) | 0.0032 (8) |
C9A | 0.0160 (10) | 0.0225 (11) | 0.0237 (10) | −0.0014 (9) | 0.0028 (8) | 0.0055 (9) |
C10A | 0.0142 (9) | 0.0209 (10) | 0.0209 (10) | −0.0022 (8) | 0.0000 (8) | 0.0007 (8) |
O10A | 0.0163 (7) | 0.0251 (8) | 0.0379 (9) | 0.0018 (6) | 0.0054 (7) | 0.0069 (7) |
C11A | 0.0177 (10) | 0.0159 (9) | 0.0183 (10) | 0.0007 (8) | −0.0010 (8) | 0.0020 (8) |
C12A | 0.0175 (10) | 0.0181 (10) | 0.0198 (10) | −0.0015 (8) | 0.0005 (8) | 0.0039 (8) |
C13A | 0.0239 (11) | 0.0161 (10) | 0.0260 (11) | −0.0029 (8) | −0.0007 (9) | −0.0002 (8) |
C14A | 0.0303 (12) | 0.0186 (10) | 0.0286 (11) | 0.0070 (10) | 0.0049 (10) | −0.0004 (9) |
C15A | 0.0193 (11) | 0.0320 (13) | 0.0425 (14) | −0.0009 (10) | 0.0066 (10) | 0.0147 (11) |
C21 | 0.0237 (11) | 0.0166 (11) | 0.0266 (11) | 0.0010 (9) | 0.0011 (9) | −0.0019 (8) |
O21 | 0.0254 (8) | 0.0179 (8) | 0.0374 (9) | 0.0021 (7) | 0.0077 (7) | 0.0029 (7) |
C22 | 0.0242 (11) | 0.0187 (11) | 0.0320 (12) | 0.0021 (9) | −0.0007 (9) | 0.0022 (9) |
O22 | 0.0307 (10) | 0.0173 (9) | 0.1096 (19) | −0.0012 (8) | 0.0240 (11) | −0.0065 (10) |
C23 | 0.0235 (11) | 0.0185 (10) | 0.0360 (12) | 0.0040 (9) | 0.0038 (9) | −0.0023 (9) |
O23 | 0.0208 (8) | 0.0320 (9) | 0.0387 (9) | 0.0013 (7) | 0.0046 (7) | 0.0118 (8) |
C24 | 0.0240 (11) | 0.0216 (11) | 0.0261 (11) | 0.0007 (9) | 0.0025 (9) | −0.0022 (9) |
O24 | 0.0399 (12) | 0.0398 (11) | 0.0748 (15) | −0.0180 (9) | −0.0261 (11) | 0.0239 (11) |
Geometric parameters (Å, º) top
C1—O1 | 1.463 (2) | N1A—C10A | 1.334 (3) |
C1—C2 | 1.527 (3) | O1A—O2A | 1.474 (2) |
C1—C11 | 1.541 (3) | C2A—H2A | 1.0000 |
C1—C12 | 1.532 (3) | C2A—O3A | 1.412 (2) |
N1—H1 | 0.89 (3) | O2A—C3A | 1.416 (2) |
N1—C2 | 1.461 (3) | C3A—O3A | 1.443 (2) |
N1—C10 | 1.342 (3) | C3A—C4A | 1.531 (3) |
O1—O2 | 1.4728 (19) | C3A—C13A | 1.511 (3) |
C2—H2 | 1.0000 | C4A—H4AA | 0.9900 |
C2—O3 | 1.413 (2) | C4A—H4AB | 0.9900 |
O2—C3 | 1.417 (2) | C4A—C5A | 1.531 (3) |
C3—O3 | 1.437 (2) | C5A—H5AA | 0.9900 |
C3—C4 | 1.533 (3) | C5A—H5AB | 0.9900 |
C3—C13 | 1.508 (3) | C5A—C11A | 1.533 (3) |
C4—H4A | 0.9900 | C6A—H6A | 1.0000 |
C4—H4B | 0.9900 | C6A—C7A | 1.531 (3) |
C4—C5 | 1.530 (3) | C6A—C11A | 1.549 (3) |
C5—H5A | 0.9900 | C6A—C14A | 1.530 (3) |
C5—H5B | 0.9900 | C7A—H7AA | 0.9900 |
C5—C11 | 1.535 (3) | C7A—H7AB | 0.9900 |
C6—H6 | 1.0000 | C7A—C8A | 1.518 (3) |
C6—C7 | 1.526 (3) | C8A—H8AA | 0.9900 |
C6—C11 | 1.546 (3) | C8A—H8AB | 0.9900 |
C6—C14 | 1.531 (3) | C8A—C12A | 1.535 (3) |
C7—H7A | 0.9900 | C9A—H9A | 1.0000 |
C7—H7B | 0.9900 | C9A—C10A | 1.511 (3) |
C7—C8 | 1.524 (3) | C9A—C12A | 1.538 (3) |
C8—H8A | 0.9900 | C9A—C15A | 1.533 (3) |
C8—H8B | 0.9900 | C10A—O10A | 1.247 (3) |
C8—C12 | 1.531 (3) | C11A—H11A | 1.0000 |
C9—H9 | 1.0000 | C12A—H12A | 1.0000 |
C9—C10 | 1.508 (3) | C13A—H13D | 0.9800 |
C9—C12 | 1.537 (3) | C13A—H13E | 0.9800 |
C9—C15 | 1.531 (3) | C13A—H13F | 0.9800 |
C10—O10 | 1.243 (3) | C14A—H14D | 0.9800 |
C11—H11 | 1.0000 | C14A—H14E | 0.9800 |
C12—H12 | 1.0000 | C14A—H14F | 0.9800 |
C13—H13A | 0.9800 | C15A—H15D | 0.9800 |
C13—H13B | 0.9800 | C15A—H15E | 0.9800 |
C13—H13C | 0.9800 | C15A—H15F | 0.9800 |
C14—H14A | 0.9800 | C21—O21 | 1.307 (3) |
C14—H14B | 0.9800 | C21—C22 | 1.496 (3) |
C14—H14C | 0.9800 | C21—O22 | 1.207 (3) |
C15—H15A | 0.9800 | O21—H21 | 0.92 (4) |
C15—H15B | 0.9800 | C22—H22 | 0.9500 |
C15—H15C | 0.9800 | C22—C23 | 1.319 (3) |
C1A—O1A | 1.465 (2) | C23—H23A | 0.9500 |
C1A—C2A | 1.529 (3) | C23—C24 | 1.495 (3) |
C1A—C11A | 1.544 (3) | O23—H23 | 0.90 (4) |
C1A—C12A | 1.532 (3) | O23—C24 | 1.310 (3) |
N1A—H1A | 0.87 (3) | C24—O24 | 1.204 (3) |
N1A—C2A | 1.464 (3) | | |
| | | |
O1—C1—C2 | 111.31 (15) | C10A—N1A—H1A | 114.9 (19) |
O1—C1—C11 | 107.05 (16) | C10A—N1A—C2A | 127.28 (18) |
O1—C1—C12 | 103.88 (15) | C1A—O1A—O2A | 111.52 (13) |
C2—C1—C11 | 110.59 (16) | C1A—C2A—H2A | 107.6 |
C2—C1—C12 | 111.58 (17) | N1A—C2A—C1A | 111.82 (16) |
C12—C1—C11 | 112.16 (16) | N1A—C2A—H2A | 107.6 |
C2—N1—H1 | 116.6 (18) | O3A—C2A—C1A | 113.83 (16) |
C10—N1—H1 | 116.4 (18) | O3A—C2A—N1A | 108.21 (16) |
C10—N1—C2 | 126.60 (18) | O3A—C2A—H2A | 107.6 |
C1—O1—O2 | 111.58 (13) | C3A—O2A—O1A | 108.45 (13) |
C1—C2—H2 | 107.1 | O2A—C3A—O3A | 108.01 (15) |
N1—C2—C1 | 112.66 (16) | O2A—C3A—C4A | 112.07 (17) |
N1—C2—H2 | 107.1 | O2A—C3A—C13A | 105.33 (16) |
O3—C2—C1 | 113.14 (16) | O3A—C3A—C4A | 110.54 (16) |
O3—C2—N1 | 109.43 (15) | O3A—C3A—C13A | 105.66 (16) |
O3—C2—H2 | 107.1 | C13A—C3A—C4A | 114.77 (18) |
C3—O2—O1 | 107.94 (13) | C2A—O3A—C3A | 113.35 (14) |
O2—C3—O3 | 107.97 (15) | C3A—C4A—H4AA | 108.7 |
O2—C3—C4 | 111.88 (16) | C3A—C4A—H4AB | 108.7 |
O2—C3—C13 | 105.56 (17) | C3A—C4A—C5A | 114.17 (17) |
O3—C3—C4 | 110.80 (17) | H4AA—C4A—H4AB | 107.6 |
O3—C3—C13 | 105.81 (16) | C5A—C4A—H4AA | 108.7 |
C13—C3—C4 | 114.40 (18) | C5A—C4A—H4AB | 108.7 |
C2—O3—C3 | 114.21 (15) | C4A—C5A—H5AA | 108.1 |
C3—C4—H4A | 108.7 | C4A—C5A—H5AB | 108.1 |
C3—C4—H4B | 108.7 | C4A—C5A—C11A | 116.71 (17) |
H4A—C4—H4B | 107.6 | H5AA—C5A—H5AB | 107.3 |
C5—C4—C3 | 114.40 (17) | C11A—C5A—H5AA | 108.1 |
C5—C4—H4A | 108.7 | C11A—C5A—H5AB | 108.1 |
C5—C4—H4B | 108.7 | C7A—C6A—H6A | 108.1 |
C4—C5—H5A | 108.0 | C7A—C6A—C11A | 110.79 (17) |
C4—C5—H5B | 108.0 | C11A—C6A—H6A | 108.1 |
C4—C5—C11 | 117.00 (18) | C14A—C6A—H6A | 108.1 |
H5A—C5—H5B | 107.3 | C14A—C6A—C7A | 110.33 (17) |
C11—C5—H5A | 108.0 | C14A—C6A—C11A | 111.42 (18) |
C11—C5—H5B | 108.0 | C6A—C7A—H7AA | 109.1 |
C7—C6—H6 | 108.1 | C6A—C7A—H7AB | 109.1 |
C7—C6—C11 | 110.47 (17) | H7AA—C7A—H7AB | 107.8 |
C7—C6—C14 | 110.66 (18) | C8A—C7A—C6A | 112.46 (17) |
C11—C6—H6 | 108.1 | C8A—C7A—H7AA | 109.1 |
C14—C6—H6 | 108.1 | C8A—C7A—H7AB | 109.1 |
C14—C6—C11 | 111.34 (18) | C7A—C8A—H8AA | 109.6 |
C6—C7—H7A | 109.2 | C7A—C8A—H8AB | 109.6 |
C6—C7—H7B | 109.2 | C7A—C8A—C12A | 110.32 (18) |
H7A—C7—H7B | 107.9 | H8AA—C8A—H8AB | 108.1 |
C8—C7—C6 | 111.98 (17) | C12A—C8A—H8AA | 109.6 |
C8—C7—H7A | 109.2 | C12A—C8A—H8AB | 109.6 |
C8—C7—H7B | 109.2 | C10A—C9A—H9A | 105.8 |
C7—C8—H8A | 109.4 | C10A—C9A—C12A | 114.48 (17) |
C7—C8—H8B | 109.4 | C10A—C9A—C15A | 110.49 (18) |
C7—C8—C12 | 110.98 (18) | C12A—C9A—H9A | 105.8 |
H8A—C8—H8B | 108.0 | C15A—C9A—H9A | 105.8 |
C12—C8—H8A | 109.4 | C15A—C9A—C12A | 113.76 (18) |
C12—C8—H8B | 109.4 | N1A—C10A—C9A | 119.20 (18) |
C10—C9—H9 | 106.1 | O10A—C10A—N1A | 121.5 (2) |
C10—C9—C12 | 113.39 (17) | O10A—C10A—C9A | 119.17 (18) |
C10—C9—C15 | 110.83 (19) | C1A—C11A—C6A | 112.24 (17) |
C12—C9—H9 | 106.1 | C1A—C11A—H11A | 106.7 |
C15—C9—H9 | 106.1 | C5A—C11A—C1A | 112.92 (16) |
C15—C9—C12 | 113.64 (18) | C5A—C11A—C6A | 111.09 (17) |
N1—C10—C9 | 118.63 (19) | C5A—C11A—H11A | 106.7 |
O10—C10—N1 | 121.7 (2) | C6A—C11A—H11A | 106.7 |
O10—C10—C9 | 119.59 (19) | C1A—C12A—C8A | 110.55 (17) |
C1—C11—C6 | 111.53 (17) | C1A—C12A—C9A | 110.87 (17) |
C1—C11—H11 | 106.7 | C1A—C12A—H12A | 106.5 |
C5—C11—C1 | 113.03 (17) | C8A—C12A—C9A | 115.35 (18) |
C5—C11—C6 | 111.83 (17) | C8A—C12A—H12A | 106.5 |
C5—C11—H11 | 106.7 | C9A—C12A—H12A | 106.5 |
C6—C11—H11 | 106.7 | C3A—C13A—H13D | 109.5 |
C1—C12—C9 | 110.22 (16) | C3A—C13A—H13E | 109.5 |
C1—C12—H12 | 107.0 | C3A—C13A—H13F | 109.5 |
C8—C12—C1 | 111.15 (17) | H13D—C13A—H13E | 109.5 |
C8—C12—C9 | 114.11 (18) | H13D—C13A—H13F | 109.5 |
C8—C12—H12 | 107.0 | H13E—C13A—H13F | 109.5 |
C9—C12—H12 | 107.0 | C6A—C14A—H14D | 109.5 |
C3—C13—H13A | 109.5 | C6A—C14A—H14E | 109.5 |
C3—C13—H13B | 109.5 | C6A—C14A—H14F | 109.5 |
C3—C13—H13C | 109.5 | H14D—C14A—H14E | 109.5 |
H13A—C13—H13B | 109.5 | H14D—C14A—H14F | 109.5 |
H13A—C13—H13C | 109.5 | H14E—C14A—H14F | 109.5 |
H13B—C13—H13C | 109.5 | C9A—C15A—H15D | 109.5 |
C6—C14—H14A | 109.5 | C9A—C15A—H15E | 109.5 |
C6—C14—H14B | 109.5 | C9A—C15A—H15F | 109.5 |
C6—C14—H14C | 109.5 | H15D—C15A—H15E | 109.5 |
H14A—C14—H14B | 109.5 | H15D—C15A—H15F | 109.5 |
H14A—C14—H14C | 109.5 | H15E—C15A—H15F | 109.5 |
H14B—C14—H14C | 109.5 | O21—C21—C22 | 111.73 (18) |
C9—C15—H15A | 109.5 | O22—C21—O21 | 124.2 (2) |
C9—C15—H15B | 109.5 | O22—C21—C22 | 124.0 (2) |
C9—C15—H15C | 109.5 | C21—O21—H21 | 109 (2) |
H15A—C15—H15B | 109.5 | C21—C22—H22 | 117.7 |
H15A—C15—H15C | 109.5 | C23—C22—C21 | 124.5 (2) |
H15B—C15—H15C | 109.5 | C23—C22—H22 | 117.7 |
O1A—C1A—C2A | 110.42 (15) | C22—C23—H23A | 118.7 |
O1A—C1A—C11A | 106.30 (16) | C22—C23—C24 | 122.5 (2) |
O1A—C1A—C12A | 104.63 (16) | C24—C23—H23A | 118.7 |
C2A—C1A—C11A | 111.69 (17) | C24—O23—H23 | 108 (2) |
C2A—C1A—C12A | 110.80 (16) | O23—C24—C23 | 112.5 (2) |
C12A—C1A—C11A | 112.66 (16) | O24—C24—C23 | 123.4 (2) |
C2A—N1A—H1A | 117.5 (19) | O24—C24—O23 | 124.1 (2) |
| | | |
C1—O1—O2—C3 | 46.72 (19) | O1A—C1A—C2A—N1A | 70.0 (2) |
C1—C2—O3—C3 | 25.7 (2) | O1A—C1A—C2A—O3A | −53.0 (2) |
N1—C2—O3—C3 | −100.77 (18) | O1A—C1A—C11A—C5A | 68.3 (2) |
O1—C1—C2—N1 | 73.3 (2) | O1A—C1A—C11A—C6A | −165.18 (15) |
O1—C1—C2—O3 | −51.5 (2) | O1A—C1A—C12A—C8A | 169.36 (16) |
O1—C1—C11—C5 | 66.4 (2) | O1A—C1A—C12A—C9A | −61.4 (2) |
O1—C1—C11—C6 | −166.56 (15) | O1A—O2A—C3A—O3A | −74.51 (18) |
O1—C1—C12—C8 | 169.06 (16) | O1A—O2A—C3A—C4A | 47.5 (2) |
O1—C1—C12—C9 | −63.4 (2) | O1A—O2A—C3A—C13A | 172.94 (15) |
O1—O2—C3—O3 | −74.63 (18) | C2A—C1A—O1A—O2A | 14.2 (2) |
O1—O2—C3—C4 | 47.5 (2) | C2A—C1A—C11A—C5A | −52.2 (2) |
O1—O2—C3—C13 | 172.56 (15) | C2A—C1A—C11A—C6A | 74.3 (2) |
C2—C1—O1—O2 | 13.5 (2) | C2A—C1A—C12A—C8A | −71.6 (2) |
C2—C1—C11—C5 | −55.0 (2) | C2A—C1A—C12A—C9A | 57.6 (2) |
C2—C1—C11—C6 | 72.0 (2) | C2A—N1A—C10A—C9A | −4.3 (3) |
C2—C1—C12—C8 | −70.9 (2) | C2A—N1A—C10A—O10A | 179.03 (19) |
C2—C1—C12—C9 | 56.6 (2) | O2A—C3A—O3A—C2A | 34.5 (2) |
C2—N1—C10—C9 | −14.0 (3) | O2A—C3A—C4A—C5A | −95.0 (2) |
C2—N1—C10—O10 | 170.1 (2) | C3A—C4A—C5A—C11A | 56.3 (2) |
O2—C3—O3—C2 | 35.3 (2) | O3A—C3A—C4A—C5A | 25.6 (2) |
O2—C3—C4—C5 | −95.3 (2) | C4A—C3A—O3A—C2A | −88.48 (19) |
C3—C4—C5—C11 | 55.0 (2) | C4A—C5A—C11A—C1A | −35.8 (3) |
O3—C3—C4—C5 | 25.2 (2) | C4A—C5A—C11A—C6A | −162.93 (17) |
C4—C3—O3—C2 | −87.49 (19) | C6A—C7A—C8A—C12A | 58.8 (2) |
C4—C5—C11—C1 | −33.3 (3) | C7A—C6A—C11A—C1A | 50.4 (2) |
C4—C5—C11—C6 | −160.11 (17) | C7A—C6A—C11A—C5A | 177.83 (17) |
C6—C7—C8—C12 | 57.4 (2) | C7A—C8A—C12A—C1A | −57.5 (2) |
C7—C6—C11—C1 | 53.8 (2) | C7A—C8A—C12A—C9A | 175.75 (17) |
C7—C6—C11—C5 | −178.55 (18) | C10A—N1A—C2A—C1A | 19.6 (3) |
C7—C8—C12—C1 | −55.4 (2) | C10A—N1A—C2A—O3A | 145.8 (2) |
C7—C8—C12—C9 | 179.25 (17) | C10A—C9A—C12A—C1A | −42.3 (2) |
C10—N1—C2—C1 | 21.6 (3) | C10A—C9A—C12A—C8A | 84.3 (2) |
C10—N1—C2—O3 | 148.36 (19) | C11A—C1A—O1A—O2A | −107.15 (16) |
C10—C9—C12—C1 | −48.4 (2) | C11A—C1A—C2A—N1A | −171.92 (16) |
C10—C9—C12—C8 | 77.5 (2) | C11A—C1A—C2A—O3A | 65.1 (2) |
C11—C1—O1—O2 | −107.45 (16) | C11A—C1A—C12A—C8A | 54.3 (2) |
C11—C1—C2—N1 | −167.84 (16) | C11A—C1A—C12A—C9A | −176.46 (16) |
C11—C1—C2—O3 | 67.4 (2) | C11A—C6A—C7A—C8A | −54.9 (2) |
C11—C1—C12—C8 | 53.8 (2) | C12A—C1A—O1A—O2A | 133.43 (15) |
C11—C1—C12—C9 | −178.66 (16) | C12A—C1A—C2A—N1A | −45.4 (2) |
C11—C6—C7—C8 | −56.3 (2) | C12A—C1A—C2A—O3A | −168.44 (16) |
C12—C1—O1—O2 | 133.72 (15) | C12A—C1A—C11A—C5A | −177.65 (17) |
C12—C1—C2—N1 | −42.2 (2) | C12A—C1A—C11A—C6A | −51.2 (2) |
C12—C1—C2—O3 | −167.02 (16) | C12A—C9A—C10A—N1A | 15.7 (3) |
C12—C1—C11—C5 | 179.76 (16) | C12A—C9A—C10A—O10A | −167.51 (19) |
C12—C1—C11—C6 | −53.2 (2) | C13A—C3A—O3A—C2A | 146.79 (17) |
C12—C9—C10—N1 | 27.2 (3) | C13A—C3A—C4A—C5A | 144.95 (18) |
C12—C9—C10—O10 | −156.8 (2) | C14A—C6A—C7A—C8A | −178.81 (18) |
C13—C3—O3—C2 | 147.99 (16) | C14A—C6A—C11A—C1A | 173.60 (17) |
C13—C3—C4—C5 | 144.73 (18) | C14A—C6A—C11A—C5A | −58.9 (2) |
C14—C6—C7—C8 | 179.95 (18) | C15A—C9A—C10A—N1A | 145.8 (2) |
C14—C6—C11—C1 | 177.17 (17) | C15A—C9A—C10A—O10A | −37.5 (3) |
C14—C6—C11—C5 | −55.2 (2) | C15A—C9A—C12A—C1A | −170.66 (18) |
C15—C9—C10—N1 | 156.3 (2) | C15A—C9A—C12A—C8A | −44.1 (3) |
C15—C9—C10—O10 | −27.6 (3) | C21—C22—C23—C24 | −1.4 (4) |
C15—C9—C12—C1 | −176.15 (18) | O21—C21—C22—C23 | 137.4 (2) |
C15—C9—C12—C8 | −50.3 (3) | C22—C23—C24—O23 | 136.1 (2) |
C1A—O1A—O2A—C3A | 46.43 (19) | C22—C23—C24—O24 | −43.3 (4) |
C1A—C2A—O3A—C3A | 27.3 (2) | O22—C21—C22—C23 | −43.8 (4) |
N1A—C2A—O3A—C3A | −97.71 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O22 | 0.89 (3) | 2.36 (3) | 3.128 (3) | 146 (2) |
N1A—H1A···O24 | 0.87 (3) | 2.26 (3) | 3.038 (3) | 149 (2) |
O21—H21···O10 | 0.92 (4) | 1.63 (4) | 2.539 (2) | 167 (3) |
O23—H23···O10A | 0.90 (4) | 1.65 (4) | 2.548 (2) | 174 (4) |
1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0
4,13.0
8,13]hexadecan-10-one–(2
E)-but-2-enedioic acid (1/1) (madiha46cult)
top
Crystal data top
2C15H23NO4·C4H4O4 | F(000) = 728 |
Mr = 678.76 | Dx = 1.325 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 9.57929 (11) Å | Cell parameters from 10873 reflections |
b = 10.05214 (16) Å | θ = 4.6–75.5° |
c = 17.7765 (2) Å | µ = 0.83 mm−1 |
β = 96.4731 (11)° | T = 100 K |
V = 1700.82 (4) Å3 | Block, colourless |
Z = 2 | 0.4 × 0.15 × 0.12 mm |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Atlas detector | 5657 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 5564 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.024 |
Detector resolution: 10.3577 pixels mm-1 | θmax = 67.5°, θmin = 4.7° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −10→12 |
Tmin = 0.546, Tmax = 1.000 | l = −21→20 |
15361 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.025 | w = 1/[σ2(Fo2) + (0.0392P)2 + 0.2051P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.066 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.15 e Å−3 |
5657 reflections | Δρmin = −0.16 e Å−3 |
455 parameters | Absolute structure: Flack x determined using 2330 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.11 (6) |
Primary atom site location: structure-invariant direct methods | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.14705 (13) | 0.01930 (15) | 0.43814 (7) | 0.0210 (3) | |
O2 | −0.16249 (13) | 0.00003 (15) | 0.51896 (7) | 0.0223 (3) | |
O3 | −0.14576 (13) | 0.22260 (14) | 0.55118 (7) | 0.0203 (3) | |
O10 | 0.30392 (13) | 0.09722 (15) | 0.52817 (7) | 0.0229 (3) | |
N11 | 0.08612 (15) | 0.17835 (18) | 0.53053 (9) | 0.0185 (3) | |
H11 | 0.112 (2) | 0.205 (3) | 0.5749 (14) | 0.026 (6)* | |
C1 | −0.10110 (18) | 0.1537 (2) | 0.42303 (10) | 0.0181 (4) | |
C2 | −0.04967 (17) | 0.2267 (2) | 0.49631 (10) | 0.0177 (4) | |
H2 | −0.0373 | 0.3223 | 0.4830 | 0.021* | |
C3 | −0.23863 (18) | 0.1106 (2) | 0.54311 (11) | 0.0218 (4) | |
C4 | −0.36889 (18) | 0.1414 (2) | 0.48717 (12) | 0.0263 (5) | |
H4A | −0.3982 | 0.0591 | 0.4591 | 0.032* | |
H4B | −0.4466 | 0.1682 | 0.5162 | 0.032* | |
C5 | −0.34649 (19) | 0.2507 (2) | 0.43025 (11) | 0.0255 (4) | |
H5A | −0.3277 | 0.3350 | 0.4584 | 0.031* | |
H5B | −0.4352 | 0.2624 | 0.3965 | 0.031* | |
C6 | −0.1824 (2) | 0.3593 (2) | 0.34533 (11) | 0.0246 (4) | |
H6 | −0.1477 | 0.4208 | 0.3876 | 0.029* | |
C7 | −0.0624 (2) | 0.3357 (2) | 0.29766 (11) | 0.0282 (5) | |
H7A | −0.0311 | 0.4223 | 0.2791 | 0.034* | |
H7B | −0.0973 | 0.2814 | 0.2530 | 0.034* | |
C8 | 0.0629 (2) | 0.2655 (2) | 0.34086 (11) | 0.0241 (4) | |
H8A | 0.1045 | 0.3235 | 0.3825 | 0.029* | |
H8B | 0.1353 | 0.2490 | 0.3064 | 0.029* | |
C9 | 0.14019 (19) | 0.0564 (2) | 0.41805 (10) | 0.0197 (4) | |
H9 | 0.1029 | −0.0345 | 0.4270 | 0.024* | |
C10 | 0.18336 (18) | 0.1151 (2) | 0.49567 (10) | 0.0193 (4) | |
C11 | −0.22729 (19) | 0.2280 (2) | 0.38059 (11) | 0.0218 (4) | |
H11A | −0.2659 | 0.1695 | 0.3377 | 0.026* | |
C12 | 0.01905 (18) | 0.1331 (2) | 0.37367 (10) | 0.0197 (4) | |
H12 | −0.0184 | 0.0758 | 0.3300 | 0.024* | |
C13 | −0.2729 (2) | 0.0746 (2) | 0.62168 (12) | 0.0300 (5) | |
H13A | −0.1869 | 0.0468 | 0.6528 | 0.045* | |
H13B | −0.3411 | 0.0016 | 0.6182 | 0.045* | |
H13C | −0.3129 | 0.1523 | 0.6448 | 0.045* | |
C14 | −0.3053 (2) | 0.4275 (3) | 0.29779 (13) | 0.0332 (5) | |
H14A | −0.2709 | 0.5058 | 0.2727 | 0.050* | |
H14B | −0.3755 | 0.4551 | 0.3307 | 0.050* | |
H14C | −0.3482 | 0.3653 | 0.2595 | 0.050* | |
C15 | 0.2678 (2) | 0.0359 (2) | 0.37455 (12) | 0.0291 (5) | |
H15A | 0.3157 | 0.1211 | 0.3699 | 0.044* | |
H15B | 0.2366 | 0.0009 | 0.3240 | 0.044* | |
H15C | 0.3326 | −0.0275 | 0.4019 | 0.044* | |
O1A | 0.81813 (12) | 0.99691 (14) | 0.98122 (6) | 0.0179 (3) | |
O2A | 0.83624 (13) | 0.85557 (14) | 0.96239 (7) | 0.0189 (3) | |
O3A | 0.81395 (12) | 0.88511 (13) | 0.83245 (7) | 0.0164 (3) | |
O10A | 0.38942 (12) | 0.88100 (14) | 0.91775 (7) | 0.0208 (3) | |
N11A | 0.58533 (15) | 0.91491 (18) | 0.86173 (9) | 0.0170 (3) | |
H11B | 0.569 (2) | 0.839 (3) | 0.8393 (13) | 0.025 (6)* | |
C1A | 0.76808 (17) | 1.07386 (19) | 0.91388 (9) | 0.0149 (4) | |
C2A | 0.71516 (17) | 0.98276 (19) | 0.84849 (10) | 0.0153 (4) | |
H2A | 0.6944 | 1.0393 | 0.8023 | 0.018* | |
C3A | 0.90985 (18) | 0.8486 (2) | 0.89763 (10) | 0.0184 (4) | |
C4A | 1.03800 (18) | 0.9410 (2) | 0.90419 (11) | 0.0216 (4) | |
H4AA | 1.0711 | 0.9538 | 0.9585 | 0.026* | |
H4AB | 1.1144 | 0.8967 | 0.8805 | 0.026* | |
C5A | 1.01141 (18) | 1.0771 (2) | 0.86762 (11) | 0.0206 (4) | |
H5AA | 0.9911 | 1.0641 | 0.8123 | 0.025* | |
H5AB | 1.0993 | 1.1294 | 0.8765 | 0.025* | |
C6A | 0.84479 (19) | 1.2720 (2) | 0.83779 (10) | 0.0199 (4) | |
H6A | 0.8106 | 1.2293 | 0.7883 | 0.024* | |
C7A | 0.7233 (2) | 1.3519 (2) | 0.86383 (11) | 0.0236 (4) | |
H7AA | 0.6907 | 1.4181 | 0.8244 | 0.028* | |
H7AB | 0.7570 | 1.4010 | 0.9107 | 0.028* | |
C8A | 0.59940 (19) | 1.2629 (2) | 0.87903 (11) | 0.0215 (4) | |
H8AA | 0.5242 | 1.3181 | 0.8969 | 0.026* | |
H8AB | 0.5607 | 1.2185 | 0.8315 | 0.026* | |
C9A | 0.53028 (18) | 1.0664 (2) | 0.96248 (10) | 0.0184 (4) | |
H9A | 0.5681 | 1.0283 | 1.0126 | 0.022* | |
C10A | 0.49670 (17) | 0.9490 (2) | 0.91108 (10) | 0.0174 (4) | |
C11A | 0.89160 (17) | 1.1607 (2) | 0.89452 (10) | 0.0172 (4) | |
H11C | 0.9309 | 1.2052 | 0.9426 | 0.021* | |
C12A | 0.64707 (17) | 1.1581 (2) | 0.93868 (10) | 0.0168 (4) | |
H12A | 0.6862 | 1.2075 | 0.9852 | 0.020* | |
C13A | 0.9415 (2) | 0.7027 (2) | 0.88912 (11) | 0.0230 (4) | |
H13D | 0.8566 | 0.6505 | 0.8941 | 0.035* | |
H13E | 1.0160 | 0.6760 | 0.9286 | 0.035* | |
H13F | 0.9724 | 0.6869 | 0.8392 | 0.035* | |
C14A | 0.9675 (2) | 1.3635 (2) | 0.82478 (12) | 0.0271 (4) | |
H14D | 1.0121 | 1.3962 | 0.8736 | 0.041* | |
H14E | 0.9326 | 1.4390 | 0.7932 | 0.041* | |
H14F | 1.0365 | 1.3138 | 0.7992 | 0.041* | |
C15A | 0.39547 (19) | 1.1407 (2) | 0.97620 (13) | 0.0294 (5) | |
H15D | 0.3515 | 1.1778 | 0.9283 | 0.044* | |
H15E | 0.4186 | 1.2130 | 1.0125 | 0.044* | |
H15F | 0.3302 | 1.0789 | 0.9966 | 0.044* | |
O21 | 0.41238 (14) | 0.26565 (17) | 0.62699 (8) | 0.0286 (3) | |
H21 | 0.368 (4) | 0.205 (4) | 0.595 (2) | 0.084 (12)* | |
O22 | 0.21229 (13) | 0.27193 (16) | 0.68154 (8) | 0.0249 (3) | |
O23 | 0.31017 (14) | 0.65994 (15) | 0.85688 (8) | 0.0237 (3) | |
H23 | 0.352 (3) | 0.742 (4) | 0.8795 (19) | 0.067 (10)* | |
O24 | 0.51070 (13) | 0.64800 (15) | 0.80351 (8) | 0.0290 (3) | |
C21 | 0.32987 (18) | 0.3129 (2) | 0.67523 (11) | 0.0210 (4) | |
C22 | 0.39656 (19) | 0.4253 (2) | 0.72062 (11) | 0.0215 (4) | |
H22 | 0.4866 | 0.4556 | 0.7107 | 0.026* | |
C23 | 0.33419 (19) | 0.4837 (2) | 0.77402 (10) | 0.0201 (4) | |
H23A | 0.2487 | 0.4482 | 0.7878 | 0.024* | |
C24 | 0.39572 (18) | 0.6052 (2) | 0.81339 (10) | 0.0201 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0235 (6) | 0.0186 (8) | 0.0215 (6) | −0.0056 (5) | 0.0051 (5) | −0.0009 (5) |
O2 | 0.0237 (6) | 0.0209 (8) | 0.0236 (6) | 0.0012 (6) | 0.0083 (5) | 0.0030 (6) |
O3 | 0.0169 (6) | 0.0227 (8) | 0.0223 (6) | −0.0005 (5) | 0.0060 (5) | −0.0026 (6) |
O10 | 0.0167 (6) | 0.0259 (8) | 0.0260 (7) | −0.0004 (5) | 0.0018 (5) | −0.0051 (6) |
N11 | 0.0161 (7) | 0.0234 (9) | 0.0158 (8) | −0.0013 (6) | 0.0011 (6) | −0.0042 (6) |
C1 | 0.0174 (8) | 0.0165 (10) | 0.0202 (9) | −0.0041 (7) | 0.0016 (7) | −0.0006 (8) |
C2 | 0.0145 (8) | 0.0195 (11) | 0.0194 (8) | −0.0009 (7) | 0.0028 (7) | −0.0013 (8) |
C3 | 0.0181 (8) | 0.0180 (11) | 0.0306 (10) | −0.0008 (8) | 0.0083 (7) | 0.0000 (8) |
C4 | 0.0158 (8) | 0.0275 (13) | 0.0361 (11) | −0.0023 (8) | 0.0049 (8) | −0.0009 (9) |
C5 | 0.0178 (9) | 0.0262 (12) | 0.0315 (10) | 0.0014 (8) | −0.0019 (7) | −0.0016 (9) |
C6 | 0.0299 (10) | 0.0217 (11) | 0.0210 (9) | −0.0001 (9) | −0.0024 (8) | −0.0013 (8) |
C7 | 0.0370 (11) | 0.0268 (13) | 0.0207 (9) | −0.0029 (9) | 0.0030 (8) | 0.0027 (9) |
C8 | 0.0268 (9) | 0.0246 (11) | 0.0216 (9) | −0.0058 (8) | 0.0060 (7) | 0.0010 (8) |
C9 | 0.0186 (8) | 0.0196 (11) | 0.0217 (9) | −0.0016 (7) | 0.0053 (7) | −0.0045 (8) |
C10 | 0.0178 (8) | 0.0180 (11) | 0.0228 (9) | −0.0040 (7) | 0.0049 (7) | −0.0012 (8) |
C11 | 0.0207 (9) | 0.0209 (11) | 0.0228 (9) | −0.0012 (8) | −0.0023 (7) | −0.0025 (8) |
C12 | 0.0204 (8) | 0.0202 (11) | 0.0188 (9) | −0.0041 (7) | 0.0035 (7) | −0.0039 (7) |
C13 | 0.0282 (10) | 0.0294 (13) | 0.0348 (11) | 0.0036 (9) | 0.0146 (8) | 0.0036 (10) |
C14 | 0.0425 (12) | 0.0256 (13) | 0.0287 (10) | 0.0069 (10) | −0.0076 (9) | −0.0017 (9) |
C15 | 0.0236 (10) | 0.0375 (14) | 0.0274 (10) | 0.0005 (9) | 0.0081 (8) | −0.0092 (9) |
O1A | 0.0212 (6) | 0.0142 (7) | 0.0180 (6) | 0.0022 (5) | 0.0005 (5) | −0.0022 (5) |
O2A | 0.0221 (6) | 0.0139 (7) | 0.0210 (6) | 0.0024 (5) | 0.0039 (5) | −0.0007 (5) |
O3A | 0.0147 (6) | 0.0157 (7) | 0.0187 (6) | 0.0018 (5) | 0.0013 (5) | −0.0022 (5) |
O10A | 0.0157 (6) | 0.0193 (8) | 0.0279 (7) | −0.0028 (5) | 0.0042 (5) | −0.0018 (6) |
N11A | 0.0143 (7) | 0.0155 (9) | 0.0209 (7) | −0.0023 (6) | 0.0002 (6) | −0.0043 (7) |
C1A | 0.0142 (8) | 0.0141 (10) | 0.0158 (8) | 0.0006 (7) | −0.0011 (6) | −0.0005 (7) |
C2A | 0.0126 (8) | 0.0143 (10) | 0.0193 (8) | −0.0010 (7) | 0.0029 (6) | −0.0004 (7) |
C3A | 0.0153 (8) | 0.0208 (11) | 0.0191 (9) | 0.0035 (7) | 0.0013 (7) | 0.0015 (8) |
C4A | 0.0143 (8) | 0.0241 (11) | 0.0260 (9) | 0.0026 (7) | 0.0012 (7) | −0.0032 (8) |
C5A | 0.0154 (8) | 0.0203 (11) | 0.0266 (9) | −0.0026 (7) | 0.0042 (7) | −0.0037 (8) |
C6A | 0.0216 (9) | 0.0157 (10) | 0.0227 (9) | −0.0032 (8) | 0.0035 (7) | −0.0004 (8) |
C7A | 0.0258 (10) | 0.0158 (11) | 0.0292 (10) | 0.0011 (8) | 0.0033 (8) | 0.0023 (8) |
C8A | 0.0171 (8) | 0.0179 (11) | 0.0289 (9) | 0.0023 (7) | 0.0008 (7) | −0.0005 (8) |
C9A | 0.0147 (8) | 0.0178 (11) | 0.0231 (9) | −0.0018 (7) | 0.0035 (7) | −0.0021 (8) |
C10A | 0.0124 (8) | 0.0187 (11) | 0.0206 (8) | 0.0010 (7) | 0.0001 (6) | 0.0026 (7) |
C11A | 0.0148 (8) | 0.0151 (10) | 0.0219 (9) | −0.0031 (7) | 0.0025 (7) | −0.0032 (8) |
C12A | 0.0139 (8) | 0.0160 (10) | 0.0205 (8) | −0.0008 (7) | 0.0020 (6) | −0.0027 (7) |
C13A | 0.0228 (9) | 0.0193 (11) | 0.0275 (9) | 0.0043 (8) | 0.0048 (7) | 0.0000 (8) |
C14A | 0.0282 (10) | 0.0192 (11) | 0.0356 (11) | −0.0053 (8) | 0.0104 (8) | 0.0011 (9) |
C15A | 0.0176 (9) | 0.0266 (13) | 0.0458 (12) | −0.0031 (8) | 0.0113 (8) | −0.0116 (10) |
O21 | 0.0190 (7) | 0.0322 (9) | 0.0349 (8) | −0.0021 (6) | 0.0041 (6) | −0.0135 (7) |
O22 | 0.0225 (7) | 0.0272 (8) | 0.0249 (6) | −0.0041 (6) | 0.0026 (5) | −0.0047 (6) |
O23 | 0.0232 (6) | 0.0233 (8) | 0.0251 (7) | −0.0049 (6) | 0.0053 (5) | −0.0051 (6) |
O24 | 0.0198 (7) | 0.0248 (9) | 0.0430 (8) | −0.0036 (6) | 0.0061 (6) | −0.0099 (7) |
C21 | 0.0191 (9) | 0.0208 (11) | 0.0222 (9) | 0.0013 (8) | −0.0017 (7) | −0.0007 (8) |
C22 | 0.0175 (8) | 0.0199 (11) | 0.0265 (9) | −0.0012 (8) | −0.0008 (7) | 0.0016 (8) |
C23 | 0.0187 (8) | 0.0180 (11) | 0.0229 (9) | −0.0026 (7) | 0.0000 (7) | 0.0024 (8) |
C24 | 0.0188 (9) | 0.0186 (11) | 0.0220 (9) | 0.0006 (7) | −0.0017 (7) | 0.0028 (7) |
Geometric parameters (Å, º) top
O1—O2 | 1.4735 (18) | N11A—H11B | 0.87 (3) |
O1—C1 | 1.456 (2) | N11A—C2A | 1.461 (2) |
O2—C3 | 1.422 (2) | N11A—C10A | 1.332 (2) |
O3—C2 | 1.415 (2) | C1A—C2A | 1.521 (2) |
O3—C3 | 1.432 (2) | C1A—C11A | 1.540 (2) |
O10—C10 | 1.245 (2) | C1A—C12A | 1.540 (2) |
N11—H11 | 0.84 (3) | C2A—H2A | 1.0000 |
N11—C2 | 1.456 (2) | C3A—C4A | 1.533 (3) |
N11—C10 | 1.337 (2) | C3A—C13A | 1.508 (3) |
C1—C2 | 1.527 (2) | C4A—H4AA | 0.9900 |
C1—C11 | 1.543 (3) | C4A—H4AB | 0.9900 |
C1—C12 | 1.538 (2) | C4A—C5A | 1.524 (3) |
C2—H2 | 1.0000 | C5A—H5AA | 0.9900 |
C3—C4 | 1.537 (3) | C5A—H5AB | 0.9900 |
C3—C13 | 1.514 (3) | C5A—C11A | 1.541 (2) |
C4—H4A | 0.9900 | C6A—H6A | 1.0000 |
C4—H4B | 0.9900 | C6A—C7A | 1.529 (3) |
C4—C5 | 1.525 (3) | C6A—C11A | 1.539 (3) |
C5—H5A | 0.9900 | C6A—C14A | 1.531 (3) |
C5—H5B | 0.9900 | C7A—H7AA | 0.9900 |
C5—C11 | 1.537 (3) | C7A—H7AB | 0.9900 |
C6—H6 | 1.0000 | C7A—C8A | 1.534 (3) |
C6—C7 | 1.522 (3) | C8A—H8AA | 0.9900 |
C6—C11 | 1.543 (3) | C8A—H8AB | 0.9900 |
C6—C14 | 1.532 (3) | C8A—C12A | 1.528 (3) |
C7—H7A | 0.9900 | C9A—H9A | 1.0000 |
C7—H7B | 0.9900 | C9A—C10A | 1.505 (3) |
C7—C8 | 1.523 (3) | C9A—C12A | 1.545 (2) |
C8—H8A | 0.9900 | C9A—C15A | 1.535 (2) |
C8—H8B | 0.9900 | C11A—H11C | 1.0000 |
C8—C12 | 1.531 (3) | C12A—H12A | 1.0000 |
C9—H9 | 1.0000 | C13A—H13D | 0.9800 |
C9—C10 | 1.515 (3) | C13A—H13E | 0.9800 |
C9—C12 | 1.535 (3) | C13A—H13F | 0.9800 |
C9—C15 | 1.532 (2) | C14A—H14D | 0.9800 |
C11—H11A | 1.0000 | C14A—H14E | 0.9800 |
C12—H12 | 1.0000 | C14A—H14F | 0.9800 |
C13—H13A | 0.9800 | C15A—H15D | 0.9800 |
C13—H13B | 0.9800 | C15A—H15E | 0.9800 |
C13—H13C | 0.9800 | C15A—H15F | 0.9800 |
C14—H14A | 0.9800 | O21—H21 | 0.91 (4) |
C14—H14B | 0.9800 | O21—C21 | 1.319 (2) |
C14—H14C | 0.9800 | O22—C21 | 1.216 (2) |
C15—H15A | 0.9800 | O23—H23 | 0.98 (4) |
C15—H15B | 0.9800 | O23—C24 | 1.310 (2) |
C15—H15C | 0.9800 | O24—C24 | 1.214 (2) |
O1A—O2A | 1.4744 (19) | C21—C22 | 1.490 (3) |
O1A—C1A | 1.460 (2) | C22—H22 | 0.9500 |
O2A—C3A | 1.418 (2) | C22—C23 | 1.316 (3) |
O3A—C2A | 1.415 (2) | C23—H23A | 0.9500 |
O3A—C3A | 1.443 (2) | C23—C24 | 1.495 (3) |
O10A—C10A | 1.251 (2) | | |
| | | |
C1—O1—O2 | 111.57 (13) | O1A—C1A—C11A | 107.08 (13) |
C3—O2—O1 | 107.64 (13) | O1A—C1A—C12A | 104.18 (13) |
C2—O3—C3 | 113.52 (14) | C2A—C1A—C11A | 111.62 (14) |
C2—N11—H11 | 116.2 (16) | C2A—C1A—C12A | 110.68 (13) |
C10—N11—H11 | 115.8 (16) | C12A—C1A—C11A | 112.00 (15) |
C10—N11—C2 | 126.99 (16) | O3A—C2A—N11A | 108.03 (15) |
O1—C1—C2 | 111.33 (15) | O3A—C2A—C1A | 113.51 (13) |
O1—C1—C11 | 107.62 (14) | O3A—C2A—H2A | 107.7 |
O1—C1—C12 | 103.95 (15) | N11A—C2A—C1A | 111.98 (14) |
C2—C1—C11 | 110.12 (16) | N11A—C2A—H2A | 107.7 |
C2—C1—C12 | 111.19 (14) | C1A—C2A—H2A | 107.7 |
C12—C1—C11 | 112.44 (15) | O2A—C3A—O3A | 108.03 (13) |
O3—C2—N11 | 108.79 (14) | O2A—C3A—C4A | 112.05 (15) |
O3—C2—C1 | 113.66 (14) | O2A—C3A—C13A | 104.69 (15) |
O3—C2—H2 | 107.2 | O3A—C3A—C4A | 109.80 (15) |
N11—C2—C1 | 112.51 (15) | O3A—C3A—C13A | 106.48 (16) |
N11—C2—H2 | 107.2 | C13A—C3A—C4A | 115.37 (15) |
C1—C2—H2 | 107.2 | C3A—C4A—H4AA | 108.6 |
O2—C3—O3 | 108.10 (13) | C3A—C4A—H4AB | 108.6 |
O2—C3—C4 | 111.66 (16) | H4AA—C4A—H4AB | 107.6 |
O2—C3—C13 | 105.32 (16) | C5A—C4A—C3A | 114.69 (14) |
O3—C3—C4 | 110.84 (16) | C5A—C4A—H4AA | 108.6 |
O3—C3—C13 | 106.97 (17) | C5A—C4A—H4AB | 108.6 |
C13—C3—C4 | 113.61 (16) | C4A—C5A—H5AA | 108.1 |
C3—C4—H4A | 108.7 | C4A—C5A—H5AB | 108.1 |
C3—C4—H4B | 108.7 | C4A—C5A—C11A | 116.83 (15) |
H4A—C4—H4B | 107.6 | H5AA—C5A—H5AB | 107.3 |
C5—C4—C3 | 114.21 (15) | C11A—C5A—H5AA | 108.1 |
C5—C4—H4A | 108.7 | C11A—C5A—H5AB | 108.1 |
C5—C4—H4B | 108.7 | C7A—C6A—H6A | 107.8 |
C4—C5—H5A | 108.2 | C7A—C6A—C11A | 111.06 (15) |
C4—C5—H5B | 108.2 | C7A—C6A—C14A | 110.75 (17) |
C4—C5—C11 | 116.33 (18) | C11A—C6A—H6A | 107.8 |
H5A—C5—H5B | 107.4 | C14A—C6A—H6A | 107.8 |
C11—C5—H5A | 108.2 | C14A—C6A—C11A | 111.34 (15) |
C11—C5—H5B | 108.2 | C6A—C7A—H7AA | 109.2 |
C7—C6—H6 | 107.9 | C6A—C7A—H7AB | 109.2 |
C7—C6—C11 | 110.80 (18) | C6A—C7A—C8A | 112.18 (17) |
C7—C6—C14 | 110.16 (17) | H7AA—C7A—H7AB | 107.9 |
C11—C6—H6 | 107.9 | C8A—C7A—H7AA | 109.2 |
C14—C6—H6 | 107.9 | C8A—C7A—H7AB | 109.2 |
C14—C6—C11 | 112.00 (17) | C7A—C8A—H8AA | 109.6 |
C6—C7—H7A | 108.9 | C7A—C8A—H8AB | 109.6 |
C6—C7—H7B | 108.9 | H8AA—C8A—H8AB | 108.1 |
C6—C7—C8 | 113.15 (16) | C12A—C8A—C7A | 110.35 (15) |
H7A—C7—H7B | 107.8 | C12A—C8A—H8AA | 109.6 |
C8—C7—H7A | 108.9 | C12A—C8A—H8AB | 109.6 |
C8—C7—H7B | 108.9 | C10A—C9A—H9A | 105.8 |
C7—C8—H8A | 109.4 | C10A—C9A—C12A | 114.43 (15) |
C7—C8—H8B | 109.4 | C10A—C9A—C15A | 110.62 (15) |
C7—C8—C12 | 111.15 (16) | C12A—C9A—H9A | 105.8 |
H8A—C8—H8B | 108.0 | C15A—C9A—H9A | 105.8 |
C12—C8—H8A | 109.4 | C15A—C9A—C12A | 113.64 (16) |
C12—C8—H8B | 109.4 | O10A—C10A—N11A | 120.89 (18) |
C10—C9—H9 | 106.1 | O10A—C10A—C9A | 119.50 (16) |
C10—C9—C12 | 112.67 (16) | N11A—C10A—C9A | 119.52 (16) |
C10—C9—C15 | 111.14 (15) | C1A—C11A—C5A | 112.24 (16) |
C12—C9—H9 | 106.1 | C1A—C11A—H11C | 106.7 |
C15—C9—H9 | 106.1 | C5A—C11A—H11C | 106.7 |
C15—C9—C12 | 114.07 (16) | C6A—C11A—C1A | 112.58 (15) |
O10—C10—N11 | 120.80 (17) | C6A—C11A—C5A | 111.42 (15) |
O10—C10—C9 | 120.69 (16) | C6A—C11A—H11C | 106.7 |
N11—C10—C9 | 118.35 (16) | C1A—C12A—C9A | 109.99 (15) |
C1—C11—H11A | 106.9 | C1A—C12A—H12A | 106.6 |
C5—C11—C1 | 112.49 (16) | C8A—C12A—C1A | 110.88 (15) |
C5—C11—C6 | 111.45 (17) | C8A—C12A—C9A | 115.63 (15) |
C5—C11—H11A | 106.9 | C8A—C12A—H12A | 106.6 |
C6—C11—C1 | 111.93 (15) | C9A—C12A—H12A | 106.6 |
C6—C11—H11A | 106.9 | C3A—C13A—H13D | 109.5 |
C1—C12—H12 | 107.1 | C3A—C13A—H13E | 109.5 |
C8—C12—C1 | 110.77 (16) | C3A—C13A—H13F | 109.5 |
C8—C12—C9 | 114.12 (15) | H13D—C13A—H13E | 109.5 |
C8—C12—H12 | 107.1 | H13D—C13A—H13F | 109.5 |
C9—C12—C1 | 110.22 (15) | H13E—C13A—H13F | 109.5 |
C9—C12—H12 | 107.1 | C6A—C14A—H14D | 109.5 |
C3—C13—H13A | 109.5 | C6A—C14A—H14E | 109.5 |
C3—C13—H13B | 109.5 | C6A—C14A—H14F | 109.5 |
C3—C13—H13C | 109.5 | H14D—C14A—H14E | 109.5 |
H13A—C13—H13B | 109.5 | H14D—C14A—H14F | 109.5 |
H13A—C13—H13C | 109.5 | H14E—C14A—H14F | 109.5 |
H13B—C13—H13C | 109.5 | C9A—C15A—H15D | 109.5 |
C6—C14—H14A | 109.5 | C9A—C15A—H15E | 109.5 |
C6—C14—H14B | 109.5 | C9A—C15A—H15F | 109.5 |
C6—C14—H14C | 109.5 | H15D—C15A—H15E | 109.5 |
H14A—C14—H14B | 109.5 | H15D—C15A—H15F | 109.5 |
H14A—C14—H14C | 109.5 | H15E—C15A—H15F | 109.5 |
H14B—C14—H14C | 109.5 | C21—O21—H21 | 112 (2) |
C9—C15—H15A | 109.5 | C24—O23—H23 | 109.9 (19) |
C9—C15—H15B | 109.5 | O21—C21—C22 | 111.93 (16) |
C9—C15—H15C | 109.5 | O22—C21—O21 | 124.56 (19) |
H15A—C15—H15B | 109.5 | O22—C21—C22 | 123.49 (17) |
H15A—C15—H15C | 109.5 | C21—C22—H22 | 119.1 |
H15B—C15—H15C | 109.5 | C23—C22—C21 | 121.83 (17) |
C1A—O1A—O2A | 111.13 (12) | C23—C22—H22 | 119.1 |
C3A—O2A—O1A | 108.31 (13) | C22—C23—H23A | 119.5 |
C2A—O3A—C3A | 113.24 (13) | C22—C23—C24 | 121.02 (17) |
C2A—N11A—H11B | 116.6 (15) | C24—C23—H23A | 119.5 |
C10A—N11A—H11B | 115.8 (15) | O23—C24—C23 | 112.32 (16) |
C10A—N11A—C2A | 127.12 (17) | O24—C24—O23 | 125.09 (19) |
O1A—C1A—C2A | 110.98 (15) | O24—C24—C23 | 122.57 (17) |
| | | |
O1—O2—C3—O3 | −75.33 (16) | O1A—C1A—C2A—O3A | −53.41 (18) |
O1—O2—C3—C4 | 46.84 (18) | O1A—C1A—C2A—N11A | 69.25 (17) |
O1—O2—C3—C13 | 170.59 (14) | O1A—C1A—C11A—C5A | 67.91 (18) |
O1—C1—C2—O3 | −51.2 (2) | O1A—C1A—C11A—C6A | −165.41 (14) |
O1—C1—C2—N11 | 72.98 (18) | O1A—C1A—C12A—C8A | 169.96 (15) |
O1—C1—C11—C5 | 67.0 (2) | O1A—C1A—C12A—C9A | −60.88 (17) |
O1—C1—C11—C6 | −166.59 (14) | O2A—O1A—C1A—C2A | 14.00 (17) |
O1—C1—C12—C8 | 170.02 (14) | O2A—O1A—C1A—C11A | −108.05 (14) |
O1—C1—C12—C9 | −62.71 (17) | O2A—O1A—C1A—C12A | 133.15 (13) |
O2—O1—C1—C2 | 13.05 (18) | O2A—C3A—C4A—C5A | −94.82 (19) |
O2—O1—C1—C11 | −107.72 (14) | O3A—C3A—C4A—C5A | 25.2 (2) |
O2—O1—C1—C12 | 132.84 (13) | C1A—O1A—O2A—C3A | 46.89 (16) |
O2—C3—C4—C5 | −96.5 (2) | C2A—O3A—C3A—O2A | 33.9 (2) |
O3—C3—C4—C5 | 24.1 (2) | C2A—O3A—C3A—C4A | −88.58 (17) |
C1—O1—O2—C3 | 46.95 (16) | C2A—O3A—C3A—C13A | 145.87 (15) |
C2—O3—C3—O2 | 36.03 (19) | C2A—N11A—C10A—O10A | −178.97 (16) |
C2—O3—C3—C4 | −86.64 (18) | C2A—N11A—C10A—C9A | −2.4 (3) |
C2—O3—C3—C13 | 149.01 (16) | C2A—C1A—C11A—C5A | −53.7 (2) |
C2—N11—C10—O10 | 168.54 (19) | C2A—C1A—C11A—C6A | 72.94 (19) |
C2—N11—C10—C9 | −16.1 (3) | C2A—C1A—C12A—C8A | −70.70 (19) |
C2—C1—C11—C5 | −54.5 (2) | C2A—C1A—C12A—C9A | 58.46 (19) |
C2—C1—C11—C6 | 71.88 (19) | C3A—O3A—C2A—N11A | −96.98 (16) |
C2—C1—C12—C8 | −70.09 (19) | C3A—O3A—C2A—C1A | 27.8 (2) |
C2—C1—C12—C9 | 57.2 (2) | C3A—C4A—C5A—C11A | 56.1 (2) |
C3—O3—C2—N11 | −101.04 (17) | C4A—C5A—C11A—C1A | −34.7 (2) |
C3—O3—C2—C1 | 25.2 (2) | C4A—C5A—C11A—C6A | −161.99 (15) |
C3—C4—C5—C11 | 57.3 (2) | C6A—C7A—C8A—C12A | 57.9 (2) |
C4—C5—C11—C1 | −34.6 (2) | C7A—C6A—C11A—C1A | 51.3 (2) |
C4—C5—C11—C6 | −161.27 (16) | C7A—C6A—C11A—C5A | 178.43 (15) |
C6—C7—C8—C12 | 56.4 (2) | C7A—C8A—C12A—C1A | −57.1 (2) |
C7—C6—C11—C1 | 51.9 (2) | C7A—C8A—C12A—C9A | 176.83 (16) |
C7—C6—C11—C5 | 178.85 (16) | C10A—N11A—C2A—O3A | 144.14 (17) |
C7—C8—C12—C1 | −55.0 (2) | C10A—N11A—C2A—C1A | 18.4 (2) |
C7—C8—C12—C9 | 179.94 (16) | C10A—C9A—C12A—C1A | −42.5 (2) |
C10—N11—C2—O3 | 149.75 (18) | C10A—C9A—C12A—C8A | 84.0 (2) |
C10—N11—C2—C1 | 22.9 (3) | C11A—C1A—C2A—O3A | 65.96 (19) |
C10—C9—C12—C1 | −49.7 (2) | C11A—C1A—C2A—N11A | −171.38 (14) |
C10—C9—C12—C8 | 75.73 (19) | C11A—C1A—C12A—C8A | 54.57 (19) |
C11—C1—C2—O3 | 68.1 (2) | C11A—C1A—C12A—C9A | −176.28 (14) |
C11—C1—C2—N11 | −167.73 (14) | C11A—C6A—C7A—C8A | −54.6 (2) |
C11—C1—C12—C8 | 53.9 (2) | C12A—C1A—C2A—O3A | −168.57 (14) |
C11—C1—C12—C9 | −178.82 (16) | C12A—C1A—C2A—N11A | −45.9 (2) |
C11—C6—C7—C8 | −54.4 (2) | C12A—C1A—C11A—C5A | −178.48 (14) |
C12—C1—C2—O3 | −166.63 (16) | C12A—C1A—C11A—C6A | −51.8 (2) |
C12—C1—C2—N11 | −42.4 (2) | C12A—C9A—C10A—O10A | −168.40 (16) |
C12—C1—C11—C5 | −179.11 (16) | C12A—C9A—C10A—N11A | 14.9 (2) |
C12—C1—C11—C6 | −52.7 (2) | C13A—C3A—C4A—C5A | 145.53 (16) |
C12—C9—C10—O10 | −155.53 (18) | C14A—C6A—C7A—C8A | −178.81 (16) |
C12—C9—C10—N11 | 29.1 (2) | C14A—C6A—C11A—C1A | 175.24 (15) |
C13—C3—C4—C5 | 144.58 (19) | C14A—C6A—C11A—C5A | −57.7 (2) |
C14—C6—C7—C8 | −178.86 (18) | C15A—C9A—C10A—O10A | −38.5 (2) |
C14—C6—C11—C1 | 175.34 (16) | C15A—C9A—C10A—N11A | 144.86 (18) |
C14—C6—C11—C5 | −57.7 (2) | C15A—C9A—C12A—C1A | −170.95 (15) |
C15—C9—C10—O10 | −26.1 (3) | C15A—C9A—C12A—C8A | −44.4 (2) |
C15—C9—C10—N11 | 158.55 (18) | O21—C21—C22—C23 | −177.50 (19) |
C15—C9—C12—C1 | −177.59 (16) | O22—C21—C22—C23 | 3.6 (3) |
C15—C9—C12—C8 | −52.2 (2) | C21—C22—C23—C24 | −173.53 (17) |
O1A—O2A—C3A—O3A | −74.54 (16) | C22—C23—C24—O23 | 171.06 (18) |
O1A—O2A—C3A—C4A | 46.53 (17) | C22—C23—C24—O24 | −7.1 (3) |
O1A—O2A—C3A—C13A | 172.27 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O22 | 0.84 (3) | 2.14 (3) | 2.970 (2) | 170 (2) |
N11A—H11B···O24 | 0.87 (3) | 2.08 (3) | 2.935 (2) | 169 (2) |
O21—H21···O10 | 0.91 (4) | 1.67 (4) | 2.573 (2) | 172 (4) |
O23—H23···O10A | 0.98 (4) | 1.58 (4) | 2.550 (2) | 169 (3) |
Geometry of lactam–acid R22(8) heterosynthons in 1–4 topCocrystal | O10···O21 (Å) | N11···O22 (Å) | Dihedral angle (°) |
1 | 2.574 (3) 2.576 (3) | 3.019 (3) 3.009 (3) | 25.7 (2) 26.3 (2) |
2 | 2.542 (2) | 2.912 (2) | 38.4 (2) |
3 | 2.539 (2) 2.549 (2) | 3.129 (3) 3.038 (3) | 20.2 (2) 37.8 (2) |
4 | 2.573 (2) 2.550 (2) | 2.970 (2) 2.935 (2) | 41.2 (2) 7.2 (2) |
Unit cells for coformers and cocrystals 1–4, all at 100 K topCompound | a | b | c | α | β | γ | V | Z | Mol. vol. | Reference |
11-Azaartemisinin | 11.718 | 11.718 | 9.487 | 90 | 90 | 120 | 1128.1 | 3 | 376.0 | Nisar et al. (2018) |
trans-Cinnamic acid | 5.5504 | 17.5427 | 7.7161 | 90 | 96.30 | 90 | 746.78 | 4 | 186.7 | Howard et al. (2009) |
1 11-Aza:Cin | 9.555 | 10.318 | 11.964 | 91.08 | 110.52 | 94.00 | 1100.8 | 2 | 550.4 | This work |
Maleic acid | 6.934 | 10.061 | 7.481 | 90 | 117.53 | 90 | 462.8 | 4 | 115.7 | This work |
2 11-Aza:Mal | 9.6216 | 10.4024 | 19.6935 | 90 | 90 | 90 | 1971.1 | 4 | 492.8 | This work |
3 11-Aza2:Mal | 9.7885 | 9.9965 | 33.766 | 90 | 90 | 90 | 3304.0 | 4 | 826.0 | This work |
Fumaric acid | 7.612 | 14.870 | 6.446 | 90 | 111.30 | 90 | 680.0 | 6 | 113.3 | This work |
4 11-Aza2:Fum | 9.579 | 10.052 | 17.776 | 90 | 96.47 | 90 | 1700.8 | 2 | 850.4 | This work |
Specific volumes for cocrystals 1–4 at 100 K topCocrystal | Acid Vol.a (Å3) | Combined Vol.b (Å3) | Cocrystal Vol.c (Å3) | Diff. Specific Vol. ΔV (Å3) |
1 11-Aza:Cin | 186.7 | 562.7 | 550.4 | -12.3 (-2.2%) |
2 11-Aza:Mal | 115.7 | 491.7 | 492.8 | +0.9 (+0.2%) |
3 11-Aza2:Mal | 115.7 | 867.7 | 826.0 | -41.7 (-4.8%) |
4 11-Aza2:Fum | 113.3 | 865.3 | 850.4 | -14.9 (-1.7%) |
Notes: (a) acid volumes from unit cells measured at 100 K (see Table 3);
(b) specific volume of 376.0 Å for 11-azaartemisinin at 100 K
(Nisar et al., 2018);
(c) corresponding combined volume from cocrystal structures
1–4. |