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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[10.3.1.04,13.08,13]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, C15H23NO4·C9H8O2). Maleic acid forms both 1:1 cocrystal 11-Aza:Mal (2, C15H23NO4·C4H4O4), in which one COOH group is involved in self-catenation, and 2:1 cocrystal 11-Aza2:Mal (3, 2C15H23NO4·C4H4O4). Its isomer, fumaric acid, only affords 2:1 cocrystal 11-Aza2: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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618006320/lf3073sup1.cif
Contains datablocks madiha47cult, madiha29cult, madiha55cult, madiha46cult, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618006320/lf3073madiha47cultsup2.hkl
Contains datablock madiha47cult

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618006320/lf3073madiha29cultsup3.hkl
Contains datablock madiha29cult

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618006320/lf3073madiha55cultsup4.hkl
Contains datablock madiha55cult

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618006320/lf3073madiha46cultsup5.hkl
Contains datablock madiha46cult

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618006320/lf3073sup6.pdf
Geometry, PXRD data, TGA data and NMR data

cdx

Chemdraw file https://doi.org/10.1107/S2053229618006320/lf3073madiha47cultsup7.cdx
Supplementary material

CCDC references: 1839352; 1839351; 1839350; 1839349

Computing details top

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[10.3.1.04,13.08,13]hexadecan-10-one–(2E)-3-Phenylprop-2-enoic acid (1/1) (madiha47cult) top
Crystal data top
C15H23NO4·C9H8O2Z = 2
Mr = 429.50F(000) = 460
Triclinic, P1Dx = 1.296 Mg m3
a = 9.5552 (4) ÅCu Kα radiation, λ = 1.54184 Å
b = 10.3175 (5) ÅCell parameters from 8241 reflections
c = 11.9645 (6) Åθ = 3.9–75.3°
α = 91.085 (4)°µ = 0.76 mm1
β = 110.515 (4)°T = 100 K
γ = 93.998 (3)°Plate, colourless
V = 1100.84 (9) Å30.2 × 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 Source6766 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.032
Detector resolution: 10.3577 pixels mm-1θmax = 67.5°, θmin = 4.0°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1212
Tmin = 0.934, Tmax = 1.000l = 1414
16397 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.00Δρmax = 0.16 e Å3
7242 reflectionsΔρmin = 0.18 e Å3
581 parametersAbsolute structure: Flack x determined using 2859 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraintsAbsolute 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
xyzUiso*/Ueq
O10.92939 (18)0.23922 (16)0.90910 (15)0.0179 (4)
O20.93313 (19)0.10373 (16)0.86936 (16)0.0196 (4)
O30.83959 (18)0.13856 (16)0.66720 (15)0.0181 (4)
O100.44598 (19)0.11831 (17)0.79596 (17)0.0231 (4)
N110.6261 (2)0.1556 (2)0.71765 (19)0.0178 (4)
H110.584 (3)0.088 (3)0.665 (3)0.023 (8)*
C10.8452 (2)0.3157 (2)0.8100 (2)0.0156 (5)
C20.7533 (2)0.2275 (2)0.7011 (2)0.0162 (5)
H20.71240.28490.63260.019*
C30.9700 (3)0.1068 (3)0.7645 (2)0.0199 (5)
C41.1033 (3)0.2056 (2)0.7772 (2)0.0209 (5)
H4A1.16610.21790.86280.025*
H4B1.16520.16880.73510.025*
C51.0595 (3)0.3376 (3)0.7283 (2)0.0204 (5)
H5A1.00660.32590.64090.024*
H5B1.15250.39420.74170.024*
C60.8854 (3)0.5194 (2)0.7022 (2)0.0186 (5)
H60.82590.48040.62070.022*
C70.7788 (3)0.5856 (2)0.7506 (2)0.0206 (5)
H7A0.83810.63430.82640.025*
H7B0.72570.64900.69280.025*
C80.6634 (3)0.4898 (2)0.7727 (2)0.0199 (5)
H8A0.59750.44630.69610.024*
H8B0.60020.53730.80700.024*
C90.6359 (3)0.2899 (2)0.8923 (2)0.0191 (5)
H90.70030.24580.96370.023*
C100.5617 (2)0.1829 (2)0.7963 (2)0.0178 (5)
C110.9596 (3)0.4090 (2)0.7818 (2)0.0170 (5)
H11B1.02730.45130.85970.020*
C120.7417 (3)0.3877 (2)0.8588 (2)0.0160 (5)
H120.80720.43580.93450.019*
C130.9972 (3)0.0316 (3)0.7412 (3)0.0254 (6)
H13A0.91650.09060.74900.038*
H13B1.09350.05250.79920.038*
H13C0.99920.04180.66010.038*
C141.0053 (3)0.6191 (2)0.6906 (3)0.0251 (6)
H14A1.07550.64770.77030.038*
H14B0.95730.69410.64910.038*
H14C1.05980.57920.64490.038*
C150.5199 (3)0.3540 (3)0.9310 (3)0.0275 (6)
H15A0.44720.39110.86180.041*
H15B0.57030.42330.99200.041*
H15C0.46770.28880.96420.041*
O1A0.30814 (19)0.69183 (16)0.03903 (15)0.0186 (4)
O2A0.30912 (19)0.55827 (16)0.00256 (16)0.0188 (4)
O3A0.39526 (18)0.61595 (17)0.20465 (15)0.0180 (4)
O10A0.7903 (2)0.64839 (19)0.08281 (18)0.0258 (4)
N11A0.6093 (2)0.6674 (2)0.15962 (19)0.0179 (4)
H11A0.651 (3)0.607 (3)0.213 (3)0.023 (8)*
C1A0.3856 (3)0.7863 (2)0.0603 (2)0.0164 (5)
C2A0.4764 (2)0.7184 (2)0.1714 (2)0.0156 (5)
H2A0.51160.78520.23920.019*
C3A0.2687 (3)0.5581 (2)0.1054 (2)0.0196 (5)
C4A0.1311 (3)0.6335 (2)0.0908 (2)0.0208 (5)
H4AA0.06840.63090.00500.025*
H4AB0.07110.58850.13340.025*
C5A0.1666 (3)0.7751 (3)0.1370 (2)0.0217 (5)
H5AA0.21910.77670.22460.026*
H5AB0.07070.81470.12210.026*
C6A0.3256 (3)0.9885 (2)0.1586 (2)0.0198 (5)
H6A0.38350.96600.24220.024*
C7A0.4308 (3)1.0683 (2)0.1120 (2)0.0227 (6)
H7AA0.47671.14440.16770.027*
H7AB0.37201.10130.03370.027*
C8A0.5556 (3)0.9919 (2)0.0976 (2)0.0196 (5)
H8AA0.61990.96400.17650.024*
H8AB0.61891.04820.06500.024*
C9A0.6023 (3)0.7924 (2)0.0146 (2)0.0195 (5)
H9A0.54410.73680.08780.023*
C10A0.6747 (3)0.6990 (2)0.0810 (2)0.0195 (5)
C11A0.2621 (3)0.8603 (2)0.0832 (2)0.0174 (5)
H11C0.19330.88490.00340.021*
C12A0.4872 (3)0.8725 (2)0.0131 (2)0.0168 (5)
H12A0.42180.90510.06440.020*
C13A0.2480 (3)0.4165 (3)0.1288 (3)0.0236 (6)
H13D0.33560.37280.12850.035*
H13E0.15800.37610.06630.035*
H13F0.23690.40860.20680.035*
C14A0.1971 (3)1.0681 (3)0.1616 (3)0.0254 (6)
H14D0.13651.08850.08000.038*
H14E0.23851.14910.20960.038*
H14F0.13401.01750.19720.038*
C15A0.7206 (3)0.8741 (3)0.0468 (3)0.0289 (6)
H15D0.78620.92630.02370.043*
H15E0.67120.93190.11040.043*
H15F0.78030.81670.07470.043*
O210.3439 (2)0.1075 (2)0.69320 (19)0.0321 (5)
H210.375 (4)0.021 (4)0.719 (3)0.033 (9)*
O220.4631 (2)0.08116 (19)0.56236 (19)0.0302 (4)
C210.3923 (3)0.1499 (3)0.6092 (3)0.0241 (6)
C220.3549 (3)0.2909 (3)0.5833 (3)0.0255 (6)
H220.29910.33610.62450.031*
C230.3953 (3)0.3579 (3)0.5052 (2)0.0228 (6)
H230.44160.30980.45880.027*
C240.3750 (3)0.4995 (3)0.4845 (2)0.0214 (5)
C250.2707 (3)0.5764 (3)0.5172 (3)0.0259 (6)
H250.20440.53580.54760.031*
C260.2623 (3)0.7104 (3)0.5059 (3)0.0284 (6)
H260.19130.76110.52940.034*
C270.3575 (3)0.7713 (3)0.4604 (3)0.0285 (6)
H270.35320.86350.45400.034*
C280.4586 (3)0.6963 (3)0.4245 (2)0.0279 (6)
H280.52230.73740.39170.033*
C290.4677 (3)0.5616 (3)0.4362 (2)0.0238 (6)
H290.53750.51120.41110.029*
O21A0.8798 (2)0.4353 (2)0.1824 (2)0.0307 (5)
H21A0.852 (5)0.523 (4)0.157 (4)0.053 (11)*
O22A0.7572 (2)0.4507 (2)0.31047 (19)0.0313 (5)
C21A0.8306 (3)0.3895 (3)0.2653 (3)0.0245 (6)
C22A0.8714 (3)0.2555 (3)0.2932 (3)0.0258 (6)
H22A0.93270.21730.25620.031*
C23A0.8256 (3)0.1862 (3)0.3683 (2)0.0224 (6)
H23A0.77250.22880.41020.027*
C24A0.8507 (3)0.0492 (3)0.3915 (2)0.0224 (6)
C25A0.9668 (3)0.0103 (3)0.3705 (3)0.0304 (6)
H25A1.03810.04090.34770.036*
C26A0.9795 (4)0.1421 (3)0.3823 (3)0.0391 (8)
H26A1.05870.18090.36690.047*
C27A0.8777 (4)0.2178 (3)0.4163 (3)0.0398 (8)
H27A0.88510.30900.42260.048*
C28A0.7651 (4)0.1603 (3)0.4412 (3)0.0362 (7)
H28A0.69620.21180.46630.043*
C29A0.7517 (3)0.0272 (3)0.4298 (2)0.0266 (6)
H29A0.67460.01160.44820.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0202 (8)0.0152 (8)0.0160 (9)0.0040 (6)0.0032 (7)0.0005 (7)
O20.0238 (9)0.0156 (8)0.0198 (9)0.0046 (7)0.0077 (7)0.0005 (7)
O30.0175 (8)0.0203 (9)0.0169 (9)0.0050 (7)0.0062 (7)0.0007 (7)
O100.0192 (8)0.0226 (9)0.0303 (10)0.0013 (7)0.0127 (8)0.0013 (8)
N110.0162 (9)0.0182 (10)0.0176 (10)0.0011 (8)0.0050 (8)0.0019 (9)
C10.0133 (10)0.0171 (12)0.0159 (12)0.0028 (9)0.0041 (9)0.0025 (10)
C20.0135 (10)0.0181 (12)0.0172 (12)0.0034 (9)0.0053 (9)0.0013 (10)
C30.0183 (11)0.0226 (13)0.0206 (13)0.0069 (10)0.0079 (10)0.0037 (10)
C40.0153 (11)0.0242 (13)0.0248 (14)0.0042 (10)0.0086 (10)0.0011 (11)
C50.0167 (11)0.0240 (13)0.0225 (14)0.0024 (9)0.0093 (10)0.0025 (10)
C60.0202 (12)0.0175 (12)0.0189 (12)0.0030 (9)0.0073 (10)0.0031 (10)
C70.0221 (12)0.0178 (12)0.0224 (13)0.0061 (10)0.0076 (10)0.0048 (10)
C80.0183 (11)0.0194 (12)0.0235 (13)0.0056 (9)0.0084 (10)0.0009 (10)
C90.0183 (11)0.0206 (12)0.0195 (13)0.0015 (9)0.0080 (10)0.0007 (10)
C100.0151 (11)0.0164 (12)0.0219 (13)0.0028 (9)0.0063 (10)0.0016 (10)
C110.0143 (11)0.0191 (12)0.0167 (12)0.0023 (9)0.0041 (9)0.0008 (10)
C120.0159 (10)0.0164 (11)0.0169 (12)0.0020 (9)0.0072 (9)0.0005 (10)
C130.0274 (13)0.0232 (14)0.0282 (15)0.0090 (10)0.0117 (11)0.0012 (11)
C140.0275 (13)0.0187 (13)0.0299 (15)0.0005 (10)0.0115 (11)0.0062 (11)
C150.0264 (13)0.0266 (14)0.0349 (16)0.0007 (11)0.0185 (12)0.0060 (12)
O1A0.0225 (8)0.0158 (8)0.0154 (9)0.0020 (7)0.0042 (7)0.0003 (7)
O2A0.0230 (8)0.0137 (8)0.0200 (9)0.0023 (6)0.0076 (7)0.0012 (7)
O3A0.0165 (8)0.0191 (8)0.0179 (9)0.0010 (6)0.0056 (7)0.0022 (7)
O10A0.0205 (9)0.0256 (9)0.0369 (11)0.0081 (7)0.0155 (8)0.0090 (8)
N11A0.0146 (9)0.0191 (10)0.0196 (11)0.0052 (8)0.0046 (8)0.0056 (9)
C1A0.0153 (10)0.0178 (12)0.0149 (11)0.0015 (9)0.0037 (9)0.0013 (10)
C2A0.0145 (11)0.0168 (12)0.0160 (12)0.0009 (9)0.0060 (9)0.0025 (9)
C3A0.0158 (11)0.0220 (13)0.0196 (13)0.0002 (9)0.0045 (10)0.0008 (10)
C4A0.0156 (11)0.0214 (13)0.0257 (14)0.0009 (9)0.0078 (10)0.0030 (11)
C5A0.0187 (11)0.0217 (13)0.0266 (14)0.0040 (9)0.0101 (10)0.0003 (11)
C6A0.0215 (12)0.0182 (12)0.0196 (12)0.0031 (9)0.0070 (10)0.0003 (10)
C7A0.0271 (13)0.0173 (12)0.0234 (14)0.0021 (10)0.0087 (11)0.0005 (10)
C8A0.0197 (12)0.0178 (12)0.0224 (13)0.0008 (9)0.0091 (10)0.0019 (10)
C9A0.0197 (12)0.0201 (12)0.0208 (13)0.0041 (10)0.0091 (10)0.0047 (10)
C10A0.0174 (11)0.0186 (12)0.0230 (13)0.0006 (9)0.0077 (10)0.0010 (10)
C11A0.0163 (11)0.0174 (12)0.0181 (12)0.0041 (9)0.0051 (9)0.0016 (10)
C12A0.0189 (11)0.0170 (12)0.0155 (12)0.0021 (9)0.0070 (9)0.0021 (10)
C13A0.0221 (12)0.0198 (13)0.0276 (14)0.0004 (10)0.0073 (11)0.0029 (11)
C14A0.0313 (14)0.0212 (13)0.0273 (14)0.0073 (11)0.0138 (12)0.0003 (11)
C15A0.0297 (14)0.0271 (14)0.0399 (17)0.0081 (11)0.0230 (13)0.0129 (12)
O210.0354 (11)0.0267 (11)0.0385 (12)0.0072 (8)0.0206 (9)0.0075 (9)
O220.0379 (11)0.0247 (10)0.0326 (11)0.0033 (8)0.0192 (9)0.0004 (9)
C210.0202 (12)0.0253 (14)0.0263 (14)0.0009 (10)0.0078 (11)0.0004 (11)
C220.0243 (13)0.0244 (14)0.0297 (15)0.0040 (10)0.0129 (11)0.0018 (11)
C230.0185 (12)0.0265 (14)0.0223 (14)0.0011 (10)0.0062 (11)0.0039 (11)
C240.0191 (11)0.0272 (14)0.0165 (12)0.0046 (10)0.0040 (10)0.0018 (10)
C250.0245 (13)0.0269 (15)0.0273 (15)0.0001 (11)0.0110 (11)0.0026 (12)
C260.0330 (15)0.0264 (14)0.0255 (15)0.0039 (11)0.0111 (12)0.0015 (12)
C270.0339 (14)0.0236 (14)0.0215 (14)0.0076 (11)0.0009 (11)0.0000 (11)
C280.0254 (13)0.0364 (16)0.0208 (14)0.0139 (11)0.0047 (11)0.0005 (12)
C290.0198 (12)0.0342 (15)0.0169 (13)0.0034 (10)0.0055 (10)0.0022 (11)
O21A0.0329 (10)0.0290 (11)0.0409 (12)0.0123 (8)0.0238 (9)0.0148 (9)
O22A0.0369 (11)0.0286 (11)0.0368 (12)0.0122 (9)0.0213 (9)0.0077 (9)
C21A0.0181 (12)0.0260 (14)0.0289 (15)0.0024 (10)0.0076 (11)0.0013 (11)
C22A0.0264 (13)0.0270 (14)0.0282 (15)0.0067 (10)0.0141 (11)0.0034 (11)
C23A0.0179 (12)0.0271 (14)0.0216 (13)0.0036 (10)0.0061 (10)0.0015 (11)
C24A0.0250 (13)0.0254 (14)0.0155 (12)0.0013 (10)0.0063 (10)0.0004 (10)
C25A0.0374 (16)0.0302 (15)0.0284 (16)0.0097 (12)0.0162 (13)0.0059 (12)
C26A0.058 (2)0.0341 (17)0.0297 (16)0.0186 (15)0.0187 (15)0.0044 (13)
C27A0.066 (2)0.0233 (15)0.0205 (15)0.0045 (14)0.0036 (15)0.0007 (12)
C28A0.0427 (17)0.0352 (17)0.0198 (15)0.0128 (13)0.0000 (13)0.0062 (12)
C29A0.0247 (13)0.0337 (15)0.0166 (13)0.0026 (11)0.0025 (10)0.0013 (11)
Geometric parameters (Å, º) top
O1—O21.475 (2)C5A—H5AB0.9900
O1—C11.460 (3)C5A—C11A1.530 (4)
O2—C31.418 (3)C6A—H6A1.0000
O3—C21.418 (3)C6A—C7A1.514 (4)
O3—C31.439 (3)C6A—C11A1.547 (3)
O10—C101.249 (3)C6A—C14A1.535 (3)
N11—H110.90 (3)C7A—H7AA0.9900
N11—C21.455 (3)C7A—H7AB0.9900
N11—C101.328 (3)C7A—C8A1.531 (3)
C1—C21.530 (3)C8A—H8AA0.9900
C1—C111.536 (3)C8A—H8AB0.9900
C1—C121.536 (3)C8A—C12A1.531 (3)
C2—H21.0000C9A—H9A1.0000
C3—C41.536 (3)C9A—C10A1.515 (4)
C3—C131.508 (3)C9A—C12A1.541 (3)
C4—H4A0.9900C9A—C15A1.524 (4)
C4—H4B0.9900C11A—H11C1.0000
C4—C51.520 (4)C12A—H12A1.0000
C5—H5A0.9900C13A—H13D0.9800
C5—H5B0.9900C13A—H13E0.9800
C5—C111.541 (3)C13A—H13F0.9800
C6—H61.0000C14A—H14D0.9800
C6—C71.529 (3)C14A—H14E0.9800
C6—C111.545 (3)C14A—H14F0.9800
C6—C141.530 (4)C15A—H15D0.9800
C7—H7A0.9900C15A—H15E0.9800
C7—H7B0.9900C15A—H15F0.9800
C7—C81.525 (4)O21—H210.93 (4)
C8—H8A0.9900O21—C211.324 (3)
C8—H8B0.9900O22—C211.220 (4)
C8—C121.530 (4)C21—C221.474 (4)
C9—H91.0000C22—H220.9500
C9—C101.520 (3)C22—C231.329 (4)
C9—C121.536 (4)C23—H230.9500
C9—C151.528 (3)C23—C241.465 (4)
C11—H11B1.0000C24—C251.396 (4)
C12—H121.0000C24—C291.398 (4)
C13—H13A0.9800C25—H250.9500
C13—H13B0.9800C25—C261.381 (4)
C13—H13C0.9800C26—H260.9500
C14—H14A0.9800C26—C271.389 (4)
C14—H14B0.9800C27—H270.9500
C14—H14C0.9800C27—C281.384 (4)
C15—H15A0.9800C28—H280.9500
C15—H15B0.9800C28—C291.388 (4)
C15—H15C0.9800C29—H290.9500
O1A—O2A1.473 (2)O21A—H21A0.98 (4)
O1A—C1A1.466 (3)O21A—C21A1.319 (4)
O2A—C3A1.413 (3)O22A—C21A1.224 (3)
O3A—C2A1.413 (3)C21A—C22A1.475 (4)
O3A—C3A1.447 (3)C22A—H22A0.9500
O10A—C10A1.248 (3)C22A—C23A1.328 (4)
N11A—H11A0.90 (3)C23A—H23A0.9500
N11A—C2A1.458 (3)C23A—C24A1.465 (4)
N11A—C10A1.333 (4)C24A—C25A1.399 (4)
C1A—C2A1.524 (3)C24A—C29A1.393 (4)
C1A—C11A1.548 (3)C25A—H25A0.9500
C1A—C12A1.528 (4)C25A—C26A1.379 (4)
C2A—H2A1.0000C26A—H26A0.9500
C3A—C4A1.533 (3)C26A—C27A1.381 (5)
C3A—C13A1.505 (4)C27A—H27A0.9500
C4A—H4AA0.9900C27A—C28A1.381 (5)
C4A—H4AB0.9900C28A—H28A0.9500
C4A—C5A1.524 (3)C28A—C29A1.392 (4)
C5A—H5AA0.9900C29A—H29A0.9500
C1—O1—O2111.60 (16)C5A—C4A—H4AA108.6
C3—O2—O1107.83 (17)C5A—C4A—H4AB108.6
C2—O3—C3113.49 (18)C4A—C5A—H5AA108.2
C2—N11—H11115 (2)C4A—C5A—H5AB108.2
C10—N11—H11117 (2)C4A—C5A—C11A116.3 (2)
C10—N11—C2127.4 (2)H5AA—C5A—H5AB107.4
O1—C1—C2110.92 (19)C11A—C5A—H5AA108.2
O1—C1—C11107.09 (17)C11A—C5A—H5AB108.2
O1—C1—C12104.17 (19)C7A—C6A—H6A108.1
C2—C1—C11111.3 (2)C7A—C6A—C11A111.8 (2)
C2—C1—C12110.68 (18)C7A—C6A—C14A110.4 (2)
C11—C1—C12112.40 (19)C11A—C6A—H6A108.1
O3—C2—N11108.92 (19)C14A—C6A—H6A108.1
O3—C2—C1113.32 (18)C14A—C6A—C11A110.1 (2)
O3—C2—H2107.3C6A—C7A—H7AA108.9
N11—C2—C1112.5 (2)C6A—C7A—H7AB108.9
N11—C2—H2107.3C6A—C7A—C8A113.4 (2)
C1—C2—H2107.3H7AA—C7A—H7AB107.7
O2—C3—O3108.00 (19)C8A—C7A—H7AA108.9
O2—C3—C4112.4 (2)C8A—C7A—H7AB108.9
O2—C3—C13104.8 (2)C7A—C8A—H8AA109.7
O3—C3—C4110.2 (2)C7A—C8A—H8AB109.7
O3—C3—C13107.2 (2)C7A—C8A—C12A109.8 (2)
C13—C3—C4113.9 (2)H8AA—C8A—H8AB108.2
C3—C4—H4A108.6C12A—C8A—H8AA109.7
C3—C4—H4B108.6C12A—C8A—H8AB109.7
H4A—C4—H4B107.6C10A—C9A—H9A105.8
C5—C4—C3114.4 (2)C10A—C9A—C12A113.8 (2)
C5—C4—H4A108.6C10A—C9A—C15A110.9 (2)
C5—C4—H4B108.6C12A—C9A—H9A105.8
C4—C5—H5A108.3C15A—C9A—H9A105.8
C4—C5—H5B108.3C15A—C9A—C12A114.0 (2)
C4—C5—C11116.1 (2)O10A—C10A—N11A120.7 (2)
H5A—C5—H5B107.4O10A—C10A—C9A120.3 (2)
C11—C5—H5A108.3N11A—C10A—C9A119.0 (2)
C11—C5—H5B108.3C1A—C11A—H11C106.7
C7—C6—H6108.1C5A—C11A—C1A112.5 (2)
C7—C6—C11111.5 (2)C5A—C11A—C6A111.4 (2)
C7—C6—C14110.5 (2)C5A—C11A—H11C106.7
C11—C6—H6108.1C6A—C11A—C1A112.39 (19)
C14—C6—H6108.1C6A—C11A—H11C106.7
C14—C6—C11110.3 (2)C1A—C12A—C8A110.5 (2)
C6—C7—H7A109.0C1A—C12A—C9A110.8 (2)
C6—C7—H7B109.0C1A—C12A—H12A106.9
H7A—C7—H7B107.8C8A—C12A—C9A114.6 (2)
C8—C7—C6113.0 (2)C8A—C12A—H12A106.9
C8—C7—H7A109.0C9A—C12A—H12A106.9
C8—C7—H7B109.0C3A—C13A—H13D109.5
C7—C8—H8A109.6C3A—C13A—H13E109.5
C7—C8—H8B109.6C3A—C13A—H13F109.5
C7—C8—C12110.37 (19)H13D—C13A—H13E109.5
H8A—C8—H8B108.1H13D—C13A—H13F109.5
C12—C8—H8A109.6H13E—C13A—H13F109.5
C12—C8—H8B109.6C6A—C14A—H14D109.5
C10—C9—H9106.1C6A—C14A—H14E109.5
C10—C9—C12113.3 (2)C6A—C14A—H14F109.5
C10—C9—C15111.1 (2)H14D—C14A—H14E109.5
C12—C9—H9106.1H14D—C14A—H14F109.5
C15—C9—H9106.1H14E—C14A—H14F109.5
C15—C9—C12113.4 (2)C9A—C15A—H15D109.5
O10—C10—N11121.1 (2)C9A—C15A—H15E109.5
O10—C10—C9119.9 (2)C9A—C15A—H15F109.5
N11—C10—C9118.9 (2)H15D—C15A—H15E109.5
C1—C11—C5112.6 (2)H15D—C15A—H15F109.5
C1—C11—C6112.55 (19)H15E—C15A—H15F109.5
C1—C11—H11B106.7C21—O21—H21115 (2)
C5—C11—C6111.1 (2)O21—C21—C22111.4 (2)
C5—C11—H11B106.7O22—C21—O21123.9 (2)
C6—C11—H11B106.7O22—C21—C22124.6 (3)
C1—C12—H12106.9C21—C22—H22118.4
C8—C12—C1110.7 (2)C23—C22—C21123.3 (3)
C8—C12—C9114.8 (2)C23—C22—H22118.4
C8—C12—H12106.9C22—C23—H23117.1
C9—C12—C1110.25 (19)C22—C23—C24125.8 (3)
C9—C12—H12106.9C24—C23—H23117.1
C3—C13—H13A109.5C25—C24—C23122.2 (2)
C3—C13—H13B109.5C25—C24—C29118.2 (2)
C3—C13—H13C109.5C29—C24—C23119.5 (3)
H13A—C13—H13B109.5C24—C25—H25119.5
H13A—C13—H13C109.5C26—C25—C24121.1 (3)
H13B—C13—H13C109.5C26—C25—H25119.5
C6—C14—H14A109.5C25—C26—H26119.9
C6—C14—H14B109.5C25—C26—C27120.2 (3)
C6—C14—H14C109.5C27—C26—H26119.9
H14A—C14—H14B109.5C26—C27—H27120.3
H14A—C14—H14C109.5C28—C27—C26119.4 (3)
H14B—C14—H14C109.5C28—C27—H27120.3
C9—C15—H15A109.5C27—C28—H28119.7
C9—C15—H15B109.5C27—C28—C29120.5 (3)
C9—C15—H15C109.5C29—C28—H28119.7
H15A—C15—H15B109.5C24—C29—H29119.8
H15A—C15—H15C109.5C28—C29—C24120.5 (3)
H15B—C15—H15C109.5C28—C29—H29119.8
C1A—O1A—O2A111.33 (17)C21A—O21A—H21A116 (2)
C3A—O2A—O1A108.75 (16)O21A—C21A—C22A111.6 (2)
C2A—O3A—C3A113.09 (19)O22A—C21A—O21A123.5 (3)
C2A—N11A—H11A115 (2)O22A—C21A—C22A124.9 (3)
C10A—N11A—H11A117.7 (19)C21A—C22A—H22A118.8
C10A—N11A—C2A127.8 (2)C23A—C22A—C21A122.5 (2)
O1A—C1A—C2A111.0 (2)C23A—C22A—H22A118.8
O1A—C1A—C11A106.24 (18)C22A—C23A—H23A117.5
O1A—C1A—C12A103.84 (19)C22A—C23A—C24A125.1 (2)
C2A—C1A—C11A111.1 (2)C24A—C23A—H23A117.5
C2A—C1A—C12A111.35 (19)C25A—C24A—C23A122.2 (3)
C12A—C1A—C11A113.0 (2)C29A—C24A—C23A119.5 (2)
O3A—C2A—N11A107.88 (19)C29A—C24A—C25A118.2 (3)
O3A—C2A—C1A114.55 (18)C24A—C25A—H25A119.5
O3A—C2A—H2A107.3C26A—C25A—C24A121.1 (3)
N11A—C2A—C1A112.2 (2)C26A—C25A—H25A119.5
N11A—C2A—H2A107.3C25A—C26A—H26A119.9
C1A—C2A—H2A107.3C25A—C26A—C27A120.3 (3)
O2A—C3A—O3A108.09 (19)C27A—C26A—H26A119.9
O2A—C3A—C4A112.7 (2)C26A—C27A—H27A120.2
O2A—C3A—C13A104.8 (2)C28A—C27A—C26A119.5 (3)
O3A—C3A—C4A109.4 (2)C28A—C27A—H27A120.2
O3A—C3A—C13A107.5 (2)C27A—C28A—H28A119.7
C13A—C3A—C4A114.0 (2)C27A—C28A—C29A120.5 (3)
C3A—C4A—H4AA108.6C29A—C28A—H28A119.7
C3A—C4A—H4AB108.6C24A—C29A—H29A119.8
H4AA—C4A—H4AB107.5C28A—C29A—C24A120.3 (3)
C5A—C4A—C3A114.8 (2)C28A—C29A—H29A119.8
O1—O2—C3—O375.1 (2)O3A—C3A—C4A—C5A26.2 (3)
O1—O2—C3—C446.6 (2)C1A—O1A—O2A—C3A46.3 (2)
O1—O2—C3—C13170.81 (17)C2A—O3A—C3A—O2A35.7 (2)
O1—C1—C2—O352.4 (3)C2A—O3A—C3A—C4A87.5 (2)
O1—C1—C2—N1171.7 (2)C2A—O3A—C3A—C13A148.2 (2)
O1—C1—C11—C568.4 (2)C2A—N11A—C10A—O10A178.8 (2)
O1—C1—C11—C6165.09 (18)C2A—N11A—C10A—C9A4.2 (4)
O1—C1—C12—C8170.72 (18)C2A—C1A—C11A—C5A50.8 (3)
O1—C1—C12—C961.1 (2)C2A—C1A—C11A—C6A76.0 (3)
O2—O1—C1—C214.0 (2)C2A—C1A—C12A—C8A70.7 (2)
O2—O1—C1—C11107.65 (19)C2A—C1A—C12A—C9A57.3 (2)
O2—O1—C1—C12133.08 (17)C3A—O3A—C2A—N11A100.5 (2)
O2—C3—C4—C595.7 (3)C3A—O3A—C2A—C1A25.3 (3)
O3—C3—C4—C524.8 (3)C3A—C4A—C5A—C11A57.1 (3)
C1—O1—O2—C346.7 (2)C4A—C5A—C11A—C1A37.5 (3)
C2—O3—C3—O235.4 (3)C4A—C5A—C11A—C6A164.8 (2)
C2—O3—C3—C487.7 (2)C6A—C7A—C8A—C12A57.8 (3)
C2—O3—C3—C13147.9 (2)C7A—C6A—C11A—C1A47.8 (3)
C2—N11—C10—O10174.9 (2)C7A—C6A—C11A—C5A175.2 (2)
C2—N11—C10—C98.5 (4)C7A—C8A—C12A—C1A57.8 (3)
C2—C1—C11—C553.0 (3)C7A—C8A—C12A—C9A176.3 (2)
C2—C1—C11—C673.5 (2)C10A—N11A—C2A—O3A144.2 (2)
C2—C1—C12—C870.0 (3)C10A—N11A—C2A—C1A17.2 (3)
C2—C1—C12—C958.2 (3)C10A—C9A—C12A—C1A44.1 (3)
C3—O3—C2—N1199.8 (2)C10A—C9A—C12A—C8A81.7 (3)
C3—O3—C2—C126.3 (3)C11A—C1A—C2A—O3A66.6 (2)
C3—C4—C5—C1157.2 (3)C11A—C1A—C2A—N11A169.95 (19)
C4—C5—C11—C136.1 (3)C11A—C1A—C12A—C8A55.1 (3)
C4—C5—C11—C6163.4 (2)C11A—C1A—C12A—C9A176.89 (19)
C6—C7—C8—C1257.0 (3)C11A—C6A—C7A—C8A52.7 (3)
C7—C6—C11—C149.3 (3)C12A—C1A—C2A—O3A166.54 (19)
C7—C6—C11—C5176.62 (19)C12A—C1A—C2A—N11A43.1 (3)
C7—C8—C12—C157.2 (2)C12A—C1A—C11A—C5A176.75 (19)
C7—C8—C12—C9177.2 (2)C12A—C1A—C11A—C6A50.0 (3)
C10—N11—C2—O3145.9 (2)C12A—C9A—C10A—O10A165.2 (2)
C10—N11—C2—C119.4 (3)C12A—C9A—C10A—N11A17.8 (3)
C10—C9—C12—C147.0 (3)C13A—C3A—C4A—C5A146.5 (2)
C10—C9—C12—C878.9 (3)C14A—C6A—C7A—C8A175.7 (2)
C11—C1—C2—O366.7 (3)C14A—C6A—C11A—C1A171.0 (2)
C11—C1—C2—N11169.17 (18)C14A—C6A—C11A—C5A61.7 (3)
C11—C1—C12—C855.1 (2)C15A—C9A—C10A—O10A35.1 (3)
C11—C1—C12—C9176.72 (19)C15A—C9A—C10A—N11A147.9 (2)
C11—C6—C7—C852.7 (3)C15A—C9A—C12A—C1A172.6 (2)
C12—C1—C2—O3167.5 (2)C15A—C9A—C12A—C8A46.8 (3)
C12—C1—C2—N1143.4 (3)O21—C21—C22—C23177.7 (3)
C12—C1—C11—C5177.76 (19)O22—C21—C22—C230.0 (5)
C12—C1—C11—C651.3 (3)C21—C22—C23—C24173.5 (2)
C12—C9—C10—O10161.0 (2)C22—C23—C24—C2520.3 (4)
C12—C9—C10—N1122.3 (3)C22—C23—C24—C29156.2 (3)
C13—C3—C4—C5145.4 (2)C23—C24—C25—C26174.5 (3)
C14—C6—C7—C8175.8 (2)C23—C24—C29—C28174.8 (2)
C14—C6—C11—C1172.5 (2)C24—C25—C26—C270.6 (4)
C14—C6—C11—C560.2 (3)C25—C24—C29—C281.8 (4)
C15—C9—C10—O1032.0 (3)C25—C26—C27—C281.2 (4)
C15—C9—C10—N11151.3 (2)C26—C27—C28—C291.4 (4)
C15—C9—C12—C1174.8 (2)C27—C28—C29—C240.1 (4)
C15—C9—C12—C848.9 (3)C29—C24—C25—C262.1 (4)
O1A—O2A—C3A—O3A74.7 (2)O21A—C21A—C22A—C23A175.5 (3)
O1A—O2A—C3A—C4A46.4 (2)O22A—C21A—C22A—C23A2.8 (4)
O1A—O2A—C3A—C13A170.94 (16)C21A—C22A—C23A—C24A174.2 (2)
O1A—C1A—C2A—O3A51.4 (3)C22A—C23A—C24A—C25A22.8 (4)
O1A—C1A—C2A—N11A72.1 (2)C22A—C23A—C24A—C29A153.7 (3)
O1A—C1A—C11A—C5A70.0 (3)C23A—C24A—C25A—C26A173.8 (3)
O1A—C1A—C11A—C6A163.2 (2)C23A—C24A—C29A—C28A173.8 (3)
O1A—C1A—C12A—C8A169.77 (19)C24A—C25A—C26A—C27A0.6 (5)
O1A—C1A—C12A—C9A62.2 (2)C25A—C24A—C29A—C28A2.9 (4)
O2A—O1A—C1A—C2A13.6 (2)C25A—C26A—C27A—C28A1.5 (5)
O2A—O1A—C1A—C11A107.2 (2)C26A—C27A—C28A—C29A1.4 (4)
O2A—O1A—C1A—C12A133.40 (17)C27A—C28A—C29A—C24A0.9 (4)
O2A—C3A—C4A—C5A94.2 (3)C29A—C24A—C25A—C26A2.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O220.90 (3)2.13 (3)3.019 (3)169 (3)
N11A—H11A···O22A0.90 (3)2.12 (3)3.009 (3)169 (3)
O21—H21···O100.93 (4)1.66 (4)2.574 (3)167 (3)
O21A—H21A···O10A0.98 (4)1.61 (4)2.576 (3)166 (4)
1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one–cis-butenedioic acid (1/1) (madiha29cult) top
Crystal data top
C15H23NO4·C4H4O4Dx = 1.339 Mg m3
Mr = 397.41Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 8948 reflections
a = 9.62162 (12) Åθ = 4.5–75.6°
b = 10.40235 (11) ŵ = 0.88 mm1
c = 19.6935 (2) ÅT = 100 K
V = 1971.08 (4) Å3Block, colourless
Z = 40.4 × 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 Source3466 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.019
Detector resolution: 10.3577 pixels mm-1θmax = 67.5°, θmin = 5.1°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1212
Tmin = 0.716, Tmax = 1.000l = 2320
11105 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.01Δρmax = 0.18 e Å3
3504 reflectionsΔρmin = 0.14 e Å3
268 parametersAbsolute structure: Flack x determined using 1483 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute 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
xyzUiso*/Ueq
O10.13170 (10)0.26302 (10)0.57995 (5)0.0174 (2)
O20.12539 (10)0.13681 (10)0.54588 (5)0.0179 (2)
O30.36214 (10)0.11255 (10)0.53420 (5)0.0166 (2)
O100.25079 (11)0.40482 (10)0.37164 (5)0.0192 (2)
N110.32147 (12)0.27619 (12)0.45656 (6)0.0156 (2)
H110.351 (2)0.224 (2)0.4254 (10)0.024 (5)*
C10.27190 (15)0.31804 (14)0.57780 (7)0.0156 (3)
C20.36156 (15)0.24771 (13)0.52617 (7)0.0147 (3)
H20.45930.27830.53230.018*
C30.24132 (15)0.06274 (14)0.56756 (8)0.0182 (3)
C40.25854 (17)0.06638 (15)0.64479 (8)0.0223 (3)
H4A0.16710.08490.66560.027*
H4B0.28820.01970.66060.027*
C50.36331 (17)0.16579 (16)0.66992 (8)0.0228 (3)
H5A0.45620.14210.65230.027*
H5B0.36750.16070.72010.027*
C60.46439 (17)0.38974 (17)0.65924 (8)0.0263 (4)
H60.53900.35420.62930.032*
C70.43671 (19)0.52849 (17)0.63734 (9)0.0296 (4)
H7A0.36780.56740.66850.035*
H7B0.52390.57850.64100.035*
C80.38249 (16)0.53724 (15)0.56482 (9)0.0231 (3)
H8A0.45390.50440.53310.028*
H8B0.36400.62830.55330.028*
C90.18497 (15)0.46594 (14)0.48504 (8)0.0168 (3)
H90.08920.42960.48950.020*
C100.25789 (14)0.38138 (13)0.43396 (7)0.0148 (3)
C110.33353 (16)0.30612 (15)0.64984 (7)0.0202 (3)
H11A0.26180.33930.68220.024*
C120.24835 (15)0.45867 (14)0.55666 (7)0.0175 (3)
H120.17850.49570.58880.021*
C130.21698 (17)0.07039 (14)0.53893 (9)0.0238 (3)
H13A0.19290.06380.49070.036*
H13B0.14060.11170.56360.036*
H13C0.30170.12190.54400.036*
C140.5169 (2)0.3851 (2)0.73242 (9)0.0398 (5)
H14A0.44210.41130.76330.060*
H14B0.59590.44370.73750.060*
H14C0.54620.29730.74340.060*
C150.16500 (18)0.60305 (15)0.45888 (8)0.0245 (3)
H15A0.25600.64240.45060.037*
H15B0.11440.65360.49280.037*
H15C0.11180.60110.41650.037*
O210.40673 (12)0.29370 (10)0.28549 (6)0.0214 (2)
H210.347 (3)0.327 (3)0.3188 (14)0.055 (7)*
O220.36344 (12)0.10985 (10)0.33941 (5)0.0226 (2)
O230.66564 (12)0.36037 (11)0.18037 (6)0.0251 (2)
H230.650 (3)0.443 (2)0.1681 (12)0.045 (6)*
O240.46072 (14)0.31992 (12)0.13105 (7)0.0345 (3)
C210.42193 (16)0.17039 (14)0.29387 (7)0.0174 (3)
C220.51583 (16)0.10315 (14)0.24596 (8)0.0190 (3)
H220.53470.01530.25530.023*
C230.57634 (16)0.15295 (14)0.19137 (7)0.0191 (3)
H23A0.63710.09820.16670.023*
C240.55830 (17)0.28680 (15)0.16494 (7)0.0191 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0117 (5)0.0174 (5)0.0230 (5)0.0015 (4)0.0026 (4)0.0019 (4)
O20.0136 (5)0.0152 (5)0.0248 (5)0.0008 (4)0.0037 (4)0.0004 (4)
O30.0133 (5)0.0161 (5)0.0203 (5)0.0012 (4)0.0016 (4)0.0016 (4)
O100.0224 (6)0.0164 (5)0.0189 (5)0.0015 (4)0.0005 (4)0.0015 (4)
N110.0155 (6)0.0145 (5)0.0169 (6)0.0017 (5)0.0018 (5)0.0024 (5)
C10.0096 (6)0.0199 (7)0.0173 (7)0.0017 (5)0.0018 (5)0.0018 (6)
C20.0118 (6)0.0163 (7)0.0158 (6)0.0000 (6)0.0003 (5)0.0011 (5)
C30.0116 (7)0.0189 (7)0.0241 (7)0.0000 (6)0.0014 (6)0.0063 (6)
C40.0183 (8)0.0263 (8)0.0223 (7)0.0020 (6)0.0001 (6)0.0080 (6)
C50.0198 (7)0.0310 (8)0.0177 (6)0.0011 (7)0.0026 (6)0.0016 (6)
C60.0217 (8)0.0323 (9)0.0250 (8)0.0039 (7)0.0048 (6)0.0087 (7)
C70.0284 (9)0.0261 (8)0.0341 (9)0.0059 (7)0.0039 (7)0.0125 (7)
C80.0195 (7)0.0185 (7)0.0313 (8)0.0042 (6)0.0024 (7)0.0055 (6)
C90.0133 (7)0.0155 (7)0.0217 (7)0.0014 (6)0.0032 (6)0.0003 (6)
C100.0112 (6)0.0133 (6)0.0199 (7)0.0033 (5)0.0012 (5)0.0002 (5)
C110.0174 (7)0.0267 (8)0.0165 (7)0.0012 (6)0.0013 (6)0.0037 (6)
C120.0150 (7)0.0165 (7)0.0210 (7)0.0003 (6)0.0033 (6)0.0038 (5)
C130.0217 (8)0.0170 (7)0.0328 (9)0.0003 (6)0.0051 (7)0.0043 (6)
C140.0399 (11)0.0489 (12)0.0308 (9)0.0073 (10)0.0131 (8)0.0106 (9)
C150.0300 (8)0.0169 (7)0.0267 (7)0.0052 (6)0.0072 (7)0.0003 (6)
O210.0283 (6)0.0132 (5)0.0228 (5)0.0028 (4)0.0055 (4)0.0004 (4)
O220.0318 (6)0.0145 (5)0.0216 (5)0.0010 (5)0.0043 (4)0.0010 (4)
O230.0264 (6)0.0154 (5)0.0336 (6)0.0006 (5)0.0014 (5)0.0023 (5)
O240.0421 (8)0.0253 (6)0.0361 (6)0.0010 (6)0.0190 (6)0.0040 (5)
C210.0195 (7)0.0154 (7)0.0174 (7)0.0011 (6)0.0038 (6)0.0014 (5)
C220.0230 (8)0.0125 (7)0.0215 (7)0.0017 (6)0.0024 (6)0.0024 (6)
C230.0213 (7)0.0152 (7)0.0208 (7)0.0014 (6)0.0014 (6)0.0046 (6)
C240.0263 (8)0.0175 (7)0.0133 (6)0.0019 (6)0.0012 (6)0.0026 (5)
Geometric parameters (Å, º) top
O1—O21.4757 (14)C8—H8B0.9900
O1—C11.4660 (17)C8—C121.536 (2)
O2—C31.4213 (17)C9—H91.0000
O3—C21.4149 (17)C9—C101.5091 (19)
O3—C31.4323 (17)C9—C121.538 (2)
O10—C101.2532 (18)C9—C151.529 (2)
N11—H110.87 (2)C11—H11A1.0000
N11—C21.4546 (18)C12—H121.0000
N11—C101.3303 (19)C13—H13A0.9800
C1—C21.5209 (19)C13—H13B0.9800
C1—C111.543 (2)C13—H13C0.9800
C1—C121.538 (2)C14—H14A0.9800
C2—H21.0000C14—H14B0.9800
C3—C41.530 (2)C14—H14C0.9800
C3—C131.513 (2)C15—H15A0.9800
C4—H4A0.9900C15—H15B0.9800
C4—H4B0.9900C15—H15C0.9800
C4—C51.527 (2)O21—H210.94 (3)
C5—H5A0.9900O21—C211.3015 (19)
C5—H5B0.9900O22—C211.2320 (19)
C5—C111.539 (2)O23—H230.90 (2)
C6—H61.0000O23—C241.321 (2)
C6—C71.530 (2)O24—C241.202 (2)
C6—C111.542 (2)C21—C221.482 (2)
C6—C141.528 (2)C22—H220.9500
C7—H7A0.9900C22—C231.328 (2)
C7—H7B0.9900C23—H23A0.9500
C7—C81.523 (2)C23—C241.497 (2)
C8—H8A0.9900
C1—O1—O2111.84 (9)C10—C9—H9105.5
C3—O2—O1108.27 (10)C10—C9—C12113.46 (12)
C2—O3—C3114.05 (10)C10—C9—C15112.19 (12)
C2—N11—H11116.8 (13)C12—C9—H9105.5
C10—N11—H11115.5 (13)C15—C9—H9105.5
C10—N11—C2127.20 (12)C15—C9—C12113.86 (12)
O1—C1—C2110.70 (11)O10—C10—N11120.84 (13)
O1—C1—C11107.20 (11)O10—C10—C9120.93 (12)
O1—C1—C12104.10 (11)N11—C10—C9118.06 (12)
C2—C1—C11110.99 (12)C1—C11—H11A107.0
C2—C1—C12111.11 (11)C5—C11—C1112.58 (12)
C12—C1—C11112.47 (12)C5—C11—C6110.63 (13)
O3—C2—N11107.98 (11)C5—C11—H11A107.0
O3—C2—C1113.92 (11)C6—C11—C1112.27 (12)
O3—C2—H2107.4C6—C11—H11A107.0
N11—C2—C1112.44 (12)C1—C12—C9110.69 (11)
N11—C2—H2107.4C1—C12—H12107.1
C1—C2—H2107.4C8—C12—C1110.73 (12)
O2—C3—O3107.64 (11)C8—C12—C9113.76 (13)
O2—C3—C4111.72 (12)C8—C12—H12107.1
O2—C3—C13105.23 (12)C9—C12—H12107.1
O3—C3—C4111.04 (12)C3—C13—H13A109.5
O3—C3—C13106.61 (12)C3—C13—H13B109.5
C13—C3—C4114.18 (13)C3—C13—H13C109.5
C3—C4—H4A108.7H13A—C13—H13B109.5
C3—C4—H4B108.7H13A—C13—H13C109.5
H4A—C4—H4B107.6H13B—C13—H13C109.5
C5—C4—C3114.23 (13)C6—C14—H14A109.5
C5—C4—H4A108.7C6—C14—H14B109.5
C5—C4—H4B108.7C6—C14—H14C109.5
C4—C5—H5A108.3H14A—C14—H14B109.5
C4—C5—H5B108.3H14A—C14—H14C109.5
C4—C5—C11115.87 (13)H14B—C14—H14C109.5
H5A—C5—H5B107.4C9—C15—H15A109.5
C11—C5—H5A108.3C9—C15—H15B109.5
C11—C5—H5B108.3C9—C15—H15C109.5
C7—C6—H6107.9H15A—C15—H15B109.5
C7—C6—C11110.88 (14)H15A—C15—H15C109.5
C11—C6—H6107.9H15B—C15—H15C109.5
C14—C6—H6107.9C21—O21—H21110.2 (16)
C14—C6—C7110.69 (15)C24—O23—H23111.1 (16)
C14—C6—C11111.42 (14)O21—C21—C22116.94 (13)
C6—C7—H7A109.1O22—C21—O21123.01 (14)
C6—C7—H7B109.1O22—C21—C22120.05 (14)
H7A—C7—H7B107.9C21—C22—H22116.6
C8—C7—C6112.35 (13)C23—C22—C21126.77 (14)
C8—C7—H7A109.1C23—C22—H22116.6
C8—C7—H7B109.1C22—C23—H23A116.8
C7—C8—H8A109.5C22—C23—C24126.43 (14)
C7—C8—H8B109.5C24—C23—H23A116.8
C7—C8—C12110.74 (14)O23—C24—C23111.61 (13)
H8A—C8—H8B108.1O24—C24—O23124.91 (14)
C12—C8—H8A109.5O24—C24—C23123.38 (14)
C12—C8—H8B109.5
O1—O2—C3—O374.51 (13)C7—C6—C11—C5178.29 (13)
O1—O2—C3—C447.64 (14)C7—C8—C12—C156.21 (16)
O1—O2—C3—C13172.07 (11)C7—C8—C12—C9178.39 (13)
O1—C1—C2—O351.62 (15)C10—N11—C2—O3152.17 (13)
O1—C1—C2—N1171.65 (14)C10—N11—C2—C125.64 (19)
O1—C1—C11—C568.73 (15)C10—C9—C12—C147.19 (16)
O1—C1—C11—C6165.63 (12)C10—C9—C12—C878.24 (15)
O1—C1—C12—C8169.41 (11)C11—C1—C2—O367.29 (15)
O1—C1—C12—C963.48 (14)C11—C1—C2—N11169.43 (12)
O2—O1—C1—C214.64 (14)C11—C1—C12—C853.70 (15)
O2—O1—C1—C11106.54 (11)C11—C1—C12—C9179.19 (12)
O2—O1—C1—C12134.10 (10)C11—C6—C7—C855.12 (18)
O2—C3—C4—C596.54 (15)C12—C1—C2—O3166.77 (11)
O3—C3—C4—C523.64 (18)C12—C1—C2—N1143.50 (15)
C1—O1—O2—C345.45 (13)C12—C1—C11—C5177.44 (12)
C2—O3—C3—O236.57 (15)C12—C1—C11—C651.81 (16)
C2—O3—C3—C486.00 (14)C12—C9—C10—O10157.01 (13)
C2—O3—C3—C13149.06 (11)C12—C9—C10—N1127.73 (18)
C2—N11—C10—O10167.29 (13)C13—C3—C4—C5144.20 (14)
C2—N11—C10—C917.5 (2)C14—C6—C7—C8179.31 (15)
C2—C1—C11—C552.27 (16)C14—C6—C11—C1175.37 (14)
C2—C1—C11—C673.37 (16)C14—C6—C11—C557.94 (18)
C2—C1—C12—C871.41 (15)C15—C9—C10—O1026.22 (19)
C2—C1—C12—C955.71 (15)C15—C9—C10—N11158.53 (13)
C3—O3—C2—N11100.94 (13)C15—C9—C12—C1177.15 (12)
C3—O3—C2—C124.72 (16)C15—C9—C12—C851.72 (17)
C3—C4—C5—C1158.32 (18)O21—C21—C22—C236.8 (2)
C4—C5—C11—C136.84 (18)O22—C21—C22—C23173.89 (16)
C4—C5—C11—C6163.36 (13)C21—C22—C23—C242.5 (3)
C6—C7—C8—C1257.80 (18)C22—C23—C24—O23102.65 (19)
C7—C6—C11—C151.59 (17)C22—C23—C24—O2480.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O220.87 (2)2.07 (2)2.9118 (16)163.0 (19)
O21—H21···O100.94 (3)1.61 (3)2.5428 (15)172 (3)
O23—H23···O22i0.90 (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[10.3.1.04,13.08,13]hexadecan-10-one–cis-butenedioic acid (2/1) (madiha55cult) top
Crystal data top
2C15H23NO4·C4H4O4Dx = 1.365 Mg m3
Mr = 678.76Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 7193 reflections
a = 9.7885 (1) Åθ = 4.6–75.4°
b = 9.9965 (1) ŵ = 0.86 mm1
c = 33.7661 (4) ÅT = 100 K
V = 3304.04 (6) Å3Block, colourless
Z = 40.2 × 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 Source5726 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 10.3577 pixels mm-1θmax = 67.5°, θmin = 4.6°
ω scansh = 1011
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 811
Tmin = 0.973, Tmax = 1.000l = 4028
9569 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.02Δρmax = 0.21 e Å3
5886 reflectionsΔρmin = 0.18 e Å3
455 parametersAbsolute structure: Flack x determined using 2414 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute 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
xyzUiso*/Ueq
C10.4239 (2)0.5209 (2)0.45667 (6)0.0152 (4)
N10.58735 (18)0.35610 (17)0.42840 (5)0.0168 (4)
H10.659 (3)0.339 (3)0.4132 (8)0.023 (6)*
O10.49755 (14)0.55528 (15)0.49297 (4)0.0181 (3)
C20.5224 (2)0.4865 (2)0.42312 (6)0.0147 (4)
H20.46730.48160.39820.018*
O20.64369 (14)0.57876 (15)0.48525 (4)0.0184 (3)
C30.6543 (2)0.6633 (2)0.45172 (6)0.0172 (4)
O30.62388 (14)0.58492 (14)0.41716 (4)0.0151 (3)
C40.5584 (2)0.7841 (2)0.45467 (6)0.0196 (4)
H4A0.54120.80330.48300.024*
H4B0.60490.86300.44320.024*
C50.4210 (2)0.7655 (2)0.43375 (6)0.0196 (4)
H5A0.43830.76060.40490.024*
H5B0.36520.84650.43860.024*
C60.2285 (2)0.6074 (2)0.41371 (6)0.0189 (4)
H60.27820.58200.38890.023*
C70.1432 (2)0.4876 (2)0.42687 (7)0.0226 (5)
H7A0.08960.51240.45060.027*
H7B0.07820.46370.40560.027*
C80.2318 (2)0.3664 (2)0.43645 (7)0.0205 (4)
H8A0.27980.33670.41220.025*
H8B0.17310.29200.44560.025*
C90.4291 (2)0.2821 (2)0.48027 (6)0.0207 (4)
H90.47580.30930.50540.025*
C100.5412 (2)0.2546 (2)0.45075 (7)0.0192 (4)
O100.59364 (17)0.14148 (15)0.44918 (6)0.0297 (4)
C110.3358 (2)0.6430 (2)0.44559 (6)0.0171 (4)
H110.28390.66850.47000.020*
C120.3369 (2)0.4000 (2)0.46856 (6)0.0176 (4)
H120.28450.42630.49280.021*
C130.8037 (2)0.6988 (2)0.44857 (7)0.0210 (4)
H13A0.85870.61700.44950.031*
H13B0.82910.75740.47070.031*
H13C0.82030.74530.42350.031*
C140.1366 (2)0.7271 (2)0.40429 (7)0.0260 (5)
H14A0.09740.76210.42890.039*
H14B0.06280.69870.38660.039*
H14C0.19070.79710.39140.039*
C150.3503 (2)0.1538 (2)0.48994 (8)0.0294 (5)
H15A0.27830.17380.50920.044*
H15B0.41310.08740.50110.044*
H15C0.30910.11820.46570.044*
C1A0.7189 (2)0.6715 (2)0.29446 (6)0.0154 (4)
N1A0.89184 (18)0.51898 (18)0.32339 (5)0.0174 (4)
H1A0.907 (3)0.443 (3)0.3348 (8)0.027 (7)*
O1A0.69096 (15)0.59186 (14)0.25893 (4)0.0178 (3)
C2A0.7575 (2)0.5804 (2)0.32907 (6)0.0149 (4)
H2A0.76260.63730.35340.018*
O2A0.67404 (15)0.44902 (14)0.26854 (4)0.0184 (3)
C3A0.5861 (2)0.4382 (2)0.30168 (6)0.0171 (4)
O3A0.66195 (14)0.47756 (14)0.33643 (4)0.0155 (3)
C4A0.4578 (2)0.5243 (2)0.29709 (6)0.0196 (4)
H4AA0.37940.47600.30890.023*
H4AB0.43860.53610.26850.023*
C5A0.4683 (2)0.6625 (2)0.31641 (6)0.0193 (4)
H5AA0.47530.64990.34540.023*
H5AB0.38200.71120.31120.023*
C6A0.6120 (2)0.8667 (2)0.33295 (6)0.0196 (4)
H6A0.63330.82620.35930.024*
C7A0.7344 (2)0.9519 (2)0.32033 (7)0.0222 (4)
H7AA0.71220.99860.29530.027*
H7AB0.75181.02080.34080.027*
C8A0.8629 (2)0.8693 (2)0.31446 (6)0.0208 (4)
H8AA0.88880.82630.33980.025*
H8AB0.93890.92830.30610.025*
C9A0.9652 (2)0.6773 (2)0.27198 (6)0.0207 (4)
H9A0.94490.63760.24540.025*
C10A0.9912 (2)0.5600 (2)0.29921 (6)0.0187 (4)
O10A1.10277 (15)0.50020 (16)0.29724 (5)0.0264 (3)
C11A0.5873 (2)0.7514 (2)0.30313 (6)0.0173 (4)
H11A0.55900.79390.27760.021*
C12A0.8391 (2)0.7614 (2)0.28285 (6)0.0185 (4)
H12A0.81110.80940.25820.022*
C13A0.5593 (2)0.2902 (2)0.30643 (7)0.0220 (4)
H13D0.64590.24120.30480.033*
H13E0.49800.25980.28530.033*
H13F0.51680.27370.33220.033*
C14A0.4847 (2)0.9543 (2)0.33759 (7)0.0258 (5)
H14D0.45830.99030.31170.039*
H14E0.50471.02820.35580.039*
H14F0.40970.90040.34830.039*
C15A1.0957 (2)0.7599 (3)0.26655 (8)0.0313 (5)
H15D1.07760.83450.24850.047*
H15E1.16770.70300.25540.047*
H15F1.12540.79480.29230.047*
C210.9037 (2)0.1337 (2)0.41140 (7)0.0223 (5)
O210.81182 (17)0.04403 (16)0.42055 (5)0.0269 (4)
H210.732 (4)0.086 (3)0.4277 (10)0.043 (9)*
C221.0388 (2)0.0711 (2)0.40218 (7)0.0249 (5)
H221.06940.00060.41880.030*
O220.8829 (2)0.25272 (18)0.41105 (8)0.0525 (6)
C231.1185 (2)0.1070 (2)0.37251 (7)0.0260 (5)
H23A1.20370.06280.36920.031*
O231.18129 (17)0.29587 (18)0.33620 (5)0.0305 (4)
H231.149 (4)0.365 (4)0.3219 (10)0.050 (10)*
C241.0798 (2)0.2144 (2)0.34383 (7)0.0239 (5)
O240.9674 (2)0.2250 (2)0.32975 (7)0.0515 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0135 (9)0.0177 (10)0.0146 (9)0.0002 (8)0.0003 (7)0.0005 (7)
N10.0141 (8)0.0145 (8)0.0218 (9)0.0010 (7)0.0042 (7)0.0001 (7)
O10.0139 (7)0.0260 (8)0.0143 (6)0.0018 (6)0.0023 (5)0.0003 (6)
C20.0129 (9)0.0150 (9)0.0161 (9)0.0014 (8)0.0007 (8)0.0008 (7)
O20.0129 (7)0.0242 (7)0.0181 (7)0.0014 (6)0.0004 (6)0.0011 (6)
C30.0187 (10)0.0186 (10)0.0143 (9)0.0015 (8)0.0005 (8)0.0017 (8)
O30.0152 (7)0.0144 (7)0.0159 (6)0.0018 (5)0.0024 (5)0.0006 (5)
C40.0195 (10)0.0161 (10)0.0233 (10)0.0034 (8)0.0035 (8)0.0024 (8)
C50.0185 (10)0.0160 (10)0.0244 (10)0.0020 (8)0.0014 (9)0.0000 (8)
C60.0149 (10)0.0196 (10)0.0222 (10)0.0014 (8)0.0004 (8)0.0024 (8)
C70.0149 (10)0.0228 (11)0.0301 (11)0.0021 (9)0.0021 (9)0.0014 (9)
C80.0154 (10)0.0188 (11)0.0273 (11)0.0037 (8)0.0001 (9)0.0020 (8)
C90.0179 (10)0.0202 (11)0.0240 (10)0.0012 (9)0.0019 (9)0.0069 (8)
C100.0147 (10)0.0160 (10)0.0269 (11)0.0009 (8)0.0008 (8)0.0023 (8)
O100.0227 (8)0.0153 (7)0.0513 (10)0.0012 (7)0.0085 (8)0.0070 (7)
C110.0145 (9)0.0173 (10)0.0194 (9)0.0015 (8)0.0029 (8)0.0005 (8)
C120.0151 (9)0.0181 (10)0.0197 (9)0.0006 (8)0.0033 (8)0.0022 (8)
C130.0164 (10)0.0230 (10)0.0234 (10)0.0024 (9)0.0010 (8)0.0025 (9)
C140.0176 (11)0.0240 (12)0.0364 (13)0.0032 (9)0.0012 (9)0.0070 (9)
C150.0234 (11)0.0227 (11)0.0421 (13)0.0011 (9)0.0077 (10)0.0138 (10)
C1A0.0164 (9)0.0164 (10)0.0133 (9)0.0004 (8)0.0013 (7)0.0002 (8)
N1A0.0154 (8)0.0165 (9)0.0205 (8)0.0008 (7)0.0011 (7)0.0044 (7)
O1A0.0243 (8)0.0146 (7)0.0144 (6)0.0018 (6)0.0004 (6)0.0011 (5)
C2A0.0132 (9)0.0159 (9)0.0156 (9)0.0022 (8)0.0005 (7)0.0000 (7)
O2A0.0230 (7)0.0133 (7)0.0189 (7)0.0001 (6)0.0031 (6)0.0010 (5)
C3A0.0170 (9)0.0180 (10)0.0164 (9)0.0024 (8)0.0001 (8)0.0013 (8)
O3A0.0156 (7)0.0160 (7)0.0150 (6)0.0024 (6)0.0008 (6)0.0009 (5)
C4A0.0154 (9)0.0187 (10)0.0247 (10)0.0017 (8)0.0010 (8)0.0007 (9)
C5A0.0158 (10)0.0170 (10)0.0251 (10)0.0022 (8)0.0013 (8)0.0003 (8)
C6A0.0257 (11)0.0148 (9)0.0183 (9)0.0023 (9)0.0005 (8)0.0006 (8)
C7A0.0270 (11)0.0156 (10)0.0239 (10)0.0026 (9)0.0035 (9)0.0005 (8)
C8A0.0210 (11)0.0171 (10)0.0243 (10)0.0052 (8)0.0036 (9)0.0032 (8)
C9A0.0160 (10)0.0225 (11)0.0237 (10)0.0014 (9)0.0028 (8)0.0055 (9)
C10A0.0142 (9)0.0209 (10)0.0209 (10)0.0022 (8)0.0000 (8)0.0007 (8)
O10A0.0163 (7)0.0251 (8)0.0379 (9)0.0018 (6)0.0054 (7)0.0069 (7)
C11A0.0177 (10)0.0159 (9)0.0183 (10)0.0007 (8)0.0010 (8)0.0020 (8)
C12A0.0175 (10)0.0181 (10)0.0198 (10)0.0015 (8)0.0005 (8)0.0039 (8)
C13A0.0239 (11)0.0161 (10)0.0260 (11)0.0029 (8)0.0007 (9)0.0002 (8)
C14A0.0303 (12)0.0186 (10)0.0286 (11)0.0070 (10)0.0049 (10)0.0004 (9)
C15A0.0193 (11)0.0320 (13)0.0425 (14)0.0009 (10)0.0066 (10)0.0147 (11)
C210.0237 (11)0.0166 (11)0.0266 (11)0.0010 (9)0.0011 (9)0.0019 (8)
O210.0254 (8)0.0179 (8)0.0374 (9)0.0021 (7)0.0077 (7)0.0029 (7)
C220.0242 (11)0.0187 (11)0.0320 (12)0.0021 (9)0.0007 (9)0.0022 (9)
O220.0307 (10)0.0173 (9)0.1096 (19)0.0012 (8)0.0240 (11)0.0065 (10)
C230.0235 (11)0.0185 (10)0.0360 (12)0.0040 (9)0.0038 (9)0.0023 (9)
O230.0208 (8)0.0320 (9)0.0387 (9)0.0013 (7)0.0046 (7)0.0118 (8)
C240.0240 (11)0.0216 (11)0.0261 (11)0.0007 (9)0.0025 (9)0.0022 (9)
O240.0399 (12)0.0398 (11)0.0748 (15)0.0180 (9)0.0261 (11)0.0239 (11)
Geometric parameters (Å, º) top
C1—O11.463 (2)N1A—C10A1.334 (3)
C1—C21.527 (3)O1A—O2A1.474 (2)
C1—C111.541 (3)C2A—H2A1.0000
C1—C121.532 (3)C2A—O3A1.412 (2)
N1—H10.89 (3)O2A—C3A1.416 (2)
N1—C21.461 (3)C3A—O3A1.443 (2)
N1—C101.342 (3)C3A—C4A1.531 (3)
O1—O21.4728 (19)C3A—C13A1.511 (3)
C2—H21.0000C4A—H4AA0.9900
C2—O31.413 (2)C4A—H4AB0.9900
O2—C31.417 (2)C4A—C5A1.531 (3)
C3—O31.437 (2)C5A—H5AA0.9900
C3—C41.533 (3)C5A—H5AB0.9900
C3—C131.508 (3)C5A—C11A1.533 (3)
C4—H4A0.9900C6A—H6A1.0000
C4—H4B0.9900C6A—C7A1.531 (3)
C4—C51.530 (3)C6A—C11A1.549 (3)
C5—H5A0.9900C6A—C14A1.530 (3)
C5—H5B0.9900C7A—H7AA0.9900
C5—C111.535 (3)C7A—H7AB0.9900
C6—H61.0000C7A—C8A1.518 (3)
C6—C71.526 (3)C8A—H8AA0.9900
C6—C111.546 (3)C8A—H8AB0.9900
C6—C141.531 (3)C8A—C12A1.535 (3)
C7—H7A0.9900C9A—H9A1.0000
C7—H7B0.9900C9A—C10A1.511 (3)
C7—C81.524 (3)C9A—C12A1.538 (3)
C8—H8A0.9900C9A—C15A1.533 (3)
C8—H8B0.9900C10A—O10A1.247 (3)
C8—C121.531 (3)C11A—H11A1.0000
C9—H91.0000C12A—H12A1.0000
C9—C101.508 (3)C13A—H13D0.9800
C9—C121.537 (3)C13A—H13E0.9800
C9—C151.531 (3)C13A—H13F0.9800
C10—O101.243 (3)C14A—H14D0.9800
C11—H111.0000C14A—H14E0.9800
C12—H121.0000C14A—H14F0.9800
C13—H13A0.9800C15A—H15D0.9800
C13—H13B0.9800C15A—H15E0.9800
C13—H13C0.9800C15A—H15F0.9800
C14—H14A0.9800C21—O211.307 (3)
C14—H14B0.9800C21—C221.496 (3)
C14—H14C0.9800C21—O221.207 (3)
C15—H15A0.9800O21—H210.92 (4)
C15—H15B0.9800C22—H220.9500
C15—H15C0.9800C22—C231.319 (3)
C1A—O1A1.465 (2)C23—H23A0.9500
C1A—C2A1.529 (3)C23—C241.495 (3)
C1A—C11A1.544 (3)O23—H230.90 (4)
C1A—C12A1.532 (3)O23—C241.310 (3)
N1A—H1A0.87 (3)C24—O241.204 (3)
N1A—C2A1.464 (3)
O1—C1—C2111.31 (15)C10A—N1A—H1A114.9 (19)
O1—C1—C11107.05 (16)C10A—N1A—C2A127.28 (18)
O1—C1—C12103.88 (15)C1A—O1A—O2A111.52 (13)
C2—C1—C11110.59 (16)C1A—C2A—H2A107.6
C2—C1—C12111.58 (17)N1A—C2A—C1A111.82 (16)
C12—C1—C11112.16 (16)N1A—C2A—H2A107.6
C2—N1—H1116.6 (18)O3A—C2A—C1A113.83 (16)
C10—N1—H1116.4 (18)O3A—C2A—N1A108.21 (16)
C10—N1—C2126.60 (18)O3A—C2A—H2A107.6
C1—O1—O2111.58 (13)C3A—O2A—O1A108.45 (13)
C1—C2—H2107.1O2A—C3A—O3A108.01 (15)
N1—C2—C1112.66 (16)O2A—C3A—C4A112.07 (17)
N1—C2—H2107.1O2A—C3A—C13A105.33 (16)
O3—C2—C1113.14 (16)O3A—C3A—C4A110.54 (16)
O3—C2—N1109.43 (15)O3A—C3A—C13A105.66 (16)
O3—C2—H2107.1C13A—C3A—C4A114.77 (18)
C3—O2—O1107.94 (13)C2A—O3A—C3A113.35 (14)
O2—C3—O3107.97 (15)C3A—C4A—H4AA108.7
O2—C3—C4111.88 (16)C3A—C4A—H4AB108.7
O2—C3—C13105.56 (17)C3A—C4A—C5A114.17 (17)
O3—C3—C4110.80 (17)H4AA—C4A—H4AB107.6
O3—C3—C13105.81 (16)C5A—C4A—H4AA108.7
C13—C3—C4114.40 (18)C5A—C4A—H4AB108.7
C2—O3—C3114.21 (15)C4A—C5A—H5AA108.1
C3—C4—H4A108.7C4A—C5A—H5AB108.1
C3—C4—H4B108.7C4A—C5A—C11A116.71 (17)
H4A—C4—H4B107.6H5AA—C5A—H5AB107.3
C5—C4—C3114.40 (17)C11A—C5A—H5AA108.1
C5—C4—H4A108.7C11A—C5A—H5AB108.1
C5—C4—H4B108.7C7A—C6A—H6A108.1
C4—C5—H5A108.0C7A—C6A—C11A110.79 (17)
C4—C5—H5B108.0C11A—C6A—H6A108.1
C4—C5—C11117.00 (18)C14A—C6A—H6A108.1
H5A—C5—H5B107.3C14A—C6A—C7A110.33 (17)
C11—C5—H5A108.0C14A—C6A—C11A111.42 (18)
C11—C5—H5B108.0C6A—C7A—H7AA109.1
C7—C6—H6108.1C6A—C7A—H7AB109.1
C7—C6—C11110.47 (17)H7AA—C7A—H7AB107.8
C7—C6—C14110.66 (18)C8A—C7A—C6A112.46 (17)
C11—C6—H6108.1C8A—C7A—H7AA109.1
C14—C6—H6108.1C8A—C7A—H7AB109.1
C14—C6—C11111.34 (18)C7A—C8A—H8AA109.6
C6—C7—H7A109.2C7A—C8A—H8AB109.6
C6—C7—H7B109.2C7A—C8A—C12A110.32 (18)
H7A—C7—H7B107.9H8AA—C8A—H8AB108.1
C8—C7—C6111.98 (17)C12A—C8A—H8AA109.6
C8—C7—H7A109.2C12A—C8A—H8AB109.6
C8—C7—H7B109.2C10A—C9A—H9A105.8
C7—C8—H8A109.4C10A—C9A—C12A114.48 (17)
C7—C8—H8B109.4C10A—C9A—C15A110.49 (18)
C7—C8—C12110.98 (18)C12A—C9A—H9A105.8
H8A—C8—H8B108.0C15A—C9A—H9A105.8
C12—C8—H8A109.4C15A—C9A—C12A113.76 (18)
C12—C8—H8B109.4N1A—C10A—C9A119.20 (18)
C10—C9—H9106.1O10A—C10A—N1A121.5 (2)
C10—C9—C12113.39 (17)O10A—C10A—C9A119.17 (18)
C10—C9—C15110.83 (19)C1A—C11A—C6A112.24 (17)
C12—C9—H9106.1C1A—C11A—H11A106.7
C15—C9—H9106.1C5A—C11A—C1A112.92 (16)
C15—C9—C12113.64 (18)C5A—C11A—C6A111.09 (17)
N1—C10—C9118.63 (19)C5A—C11A—H11A106.7
O10—C10—N1121.7 (2)C6A—C11A—H11A106.7
O10—C10—C9119.59 (19)C1A—C12A—C8A110.55 (17)
C1—C11—C6111.53 (17)C1A—C12A—C9A110.87 (17)
C1—C11—H11106.7C1A—C12A—H12A106.5
C5—C11—C1113.03 (17)C8A—C12A—C9A115.35 (18)
C5—C11—C6111.83 (17)C8A—C12A—H12A106.5
C5—C11—H11106.7C9A—C12A—H12A106.5
C6—C11—H11106.7C3A—C13A—H13D109.5
C1—C12—C9110.22 (16)C3A—C13A—H13E109.5
C1—C12—H12107.0C3A—C13A—H13F109.5
C8—C12—C1111.15 (17)H13D—C13A—H13E109.5
C8—C12—C9114.11 (18)H13D—C13A—H13F109.5
C8—C12—H12107.0H13E—C13A—H13F109.5
C9—C12—H12107.0C6A—C14A—H14D109.5
C3—C13—H13A109.5C6A—C14A—H14E109.5
C3—C13—H13B109.5C6A—C14A—H14F109.5
C3—C13—H13C109.5H14D—C14A—H14E109.5
H13A—C13—H13B109.5H14D—C14A—H14F109.5
H13A—C13—H13C109.5H14E—C14A—H14F109.5
H13B—C13—H13C109.5C9A—C15A—H15D109.5
C6—C14—H14A109.5C9A—C15A—H15E109.5
C6—C14—H14B109.5C9A—C15A—H15F109.5
C6—C14—H14C109.5H15D—C15A—H15E109.5
H14A—C14—H14B109.5H15D—C15A—H15F109.5
H14A—C14—H14C109.5H15E—C15A—H15F109.5
H14B—C14—H14C109.5O21—C21—C22111.73 (18)
C9—C15—H15A109.5O22—C21—O21124.2 (2)
C9—C15—H15B109.5O22—C21—C22124.0 (2)
C9—C15—H15C109.5C21—O21—H21109 (2)
H15A—C15—H15B109.5C21—C22—H22117.7
H15A—C15—H15C109.5C23—C22—C21124.5 (2)
H15B—C15—H15C109.5C23—C22—H22117.7
O1A—C1A—C2A110.42 (15)C22—C23—H23A118.7
O1A—C1A—C11A106.30 (16)C22—C23—C24122.5 (2)
O1A—C1A—C12A104.63 (16)C24—C23—H23A118.7
C2A—C1A—C11A111.69 (17)C24—O23—H23108 (2)
C2A—C1A—C12A110.80 (16)O23—C24—C23112.5 (2)
C12A—C1A—C11A112.66 (16)O24—C24—C23123.4 (2)
C2A—N1A—H1A117.5 (19)O24—C24—O23124.1 (2)
C1—O1—O2—C346.72 (19)O1A—C1A—C2A—N1A70.0 (2)
C1—C2—O3—C325.7 (2)O1A—C1A—C2A—O3A53.0 (2)
N1—C2—O3—C3100.77 (18)O1A—C1A—C11A—C5A68.3 (2)
O1—C1—C2—N173.3 (2)O1A—C1A—C11A—C6A165.18 (15)
O1—C1—C2—O351.5 (2)O1A—C1A—C12A—C8A169.36 (16)
O1—C1—C11—C566.4 (2)O1A—C1A—C12A—C9A61.4 (2)
O1—C1—C11—C6166.56 (15)O1A—O2A—C3A—O3A74.51 (18)
O1—C1—C12—C8169.06 (16)O1A—O2A—C3A—C4A47.5 (2)
O1—C1—C12—C963.4 (2)O1A—O2A—C3A—C13A172.94 (15)
O1—O2—C3—O374.63 (18)C2A—C1A—O1A—O2A14.2 (2)
O1—O2—C3—C447.5 (2)C2A—C1A—C11A—C5A52.2 (2)
O1—O2—C3—C13172.56 (15)C2A—C1A—C11A—C6A74.3 (2)
C2—C1—O1—O213.5 (2)C2A—C1A—C12A—C8A71.6 (2)
C2—C1—C11—C555.0 (2)C2A—C1A—C12A—C9A57.6 (2)
C2—C1—C11—C672.0 (2)C2A—N1A—C10A—C9A4.3 (3)
C2—C1—C12—C870.9 (2)C2A—N1A—C10A—O10A179.03 (19)
C2—C1—C12—C956.6 (2)O2A—C3A—O3A—C2A34.5 (2)
C2—N1—C10—C914.0 (3)O2A—C3A—C4A—C5A95.0 (2)
C2—N1—C10—O10170.1 (2)C3A—C4A—C5A—C11A56.3 (2)
O2—C3—O3—C235.3 (2)O3A—C3A—C4A—C5A25.6 (2)
O2—C3—C4—C595.3 (2)C4A—C3A—O3A—C2A88.48 (19)
C3—C4—C5—C1155.0 (2)C4A—C5A—C11A—C1A35.8 (3)
O3—C3—C4—C525.2 (2)C4A—C5A—C11A—C6A162.93 (17)
C4—C3—O3—C287.49 (19)C6A—C7A—C8A—C12A58.8 (2)
C4—C5—C11—C133.3 (3)C7A—C6A—C11A—C1A50.4 (2)
C4—C5—C11—C6160.11 (17)C7A—C6A—C11A—C5A177.83 (17)
C6—C7—C8—C1257.4 (2)C7A—C8A—C12A—C1A57.5 (2)
C7—C6—C11—C153.8 (2)C7A—C8A—C12A—C9A175.75 (17)
C7—C6—C11—C5178.55 (18)C10A—N1A—C2A—C1A19.6 (3)
C7—C8—C12—C155.4 (2)C10A—N1A—C2A—O3A145.8 (2)
C7—C8—C12—C9179.25 (17)C10A—C9A—C12A—C1A42.3 (2)
C10—N1—C2—C121.6 (3)C10A—C9A—C12A—C8A84.3 (2)
C10—N1—C2—O3148.36 (19)C11A—C1A—O1A—O2A107.15 (16)
C10—C9—C12—C148.4 (2)C11A—C1A—C2A—N1A171.92 (16)
C10—C9—C12—C877.5 (2)C11A—C1A—C2A—O3A65.1 (2)
C11—C1—O1—O2107.45 (16)C11A—C1A—C12A—C8A54.3 (2)
C11—C1—C2—N1167.84 (16)C11A—C1A—C12A—C9A176.46 (16)
C11—C1—C2—O367.4 (2)C11A—C6A—C7A—C8A54.9 (2)
C11—C1—C12—C853.8 (2)C12A—C1A—O1A—O2A133.43 (15)
C11—C1—C12—C9178.66 (16)C12A—C1A—C2A—N1A45.4 (2)
C11—C6—C7—C856.3 (2)C12A—C1A—C2A—O3A168.44 (16)
C12—C1—O1—O2133.72 (15)C12A—C1A—C11A—C5A177.65 (17)
C12—C1—C2—N142.2 (2)C12A—C1A—C11A—C6A51.2 (2)
C12—C1—C2—O3167.02 (16)C12A—C9A—C10A—N1A15.7 (3)
C12—C1—C11—C5179.76 (16)C12A—C9A—C10A—O10A167.51 (19)
C12—C1—C11—C653.2 (2)C13A—C3A—O3A—C2A146.79 (17)
C12—C9—C10—N127.2 (3)C13A—C3A—C4A—C5A144.95 (18)
C12—C9—C10—O10156.8 (2)C14A—C6A—C7A—C8A178.81 (18)
C13—C3—O3—C2147.99 (16)C14A—C6A—C11A—C1A173.60 (17)
C13—C3—C4—C5144.73 (18)C14A—C6A—C11A—C5A58.9 (2)
C14—C6—C7—C8179.95 (18)C15A—C9A—C10A—N1A145.8 (2)
C14—C6—C11—C1177.17 (17)C15A—C9A—C10A—O10A37.5 (3)
C14—C6—C11—C555.2 (2)C15A—C9A—C12A—C1A170.66 (18)
C15—C9—C10—N1156.3 (2)C15A—C9A—C12A—C8A44.1 (3)
C15—C9—C10—O1027.6 (3)C21—C22—C23—C241.4 (4)
C15—C9—C12—C1176.15 (18)O21—C21—C22—C23137.4 (2)
C15—C9—C12—C850.3 (3)C22—C23—C24—O23136.1 (2)
C1A—O1A—O2A—C3A46.43 (19)C22—C23—C24—O2443.3 (4)
C1A—C2A—O3A—C3A27.3 (2)O22—C21—C22—C2343.8 (4)
N1A—C2A—O3A—C3A97.71 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O220.89 (3)2.36 (3)3.128 (3)146 (2)
N1A—H1A···O240.87 (3)2.26 (3)3.038 (3)149 (2)
O21—H21···O100.92 (4)1.63 (4)2.539 (2)167 (3)
O23—H23···O10A0.90 (4)1.65 (4)2.548 (2)174 (4)
1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one–(2E)-but-2-enedioic acid (1/1) (madiha46cult) top
Crystal data top
2C15H23NO4·C4H4O4F(000) = 728
Mr = 678.76Dx = 1.325 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 9.57929 (11) ÅCell parameters from 10873 reflections
b = 10.05214 (16) Åθ = 4.6–75.5°
c = 17.7765 (2) ŵ = 0.83 mm1
β = 96.4731 (11)°T = 100 K
V = 1700.82 (4) Å3Block, colourless
Z = 20.4 × 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 Source5564 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.024
Detector resolution: 10.3577 pixels mm-1θmax = 67.5°, θmin = 4.7°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1012
Tmin = 0.546, Tmax = 1.000l = 2120
15361 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.02Δρmax = 0.15 e Å3
5657 reflectionsΔρmin = 0.16 e Å3
455 parametersAbsolute structure: Flack x determined using 2330 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute 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
xyzUiso*/Ueq
O10.14705 (13)0.01930 (15)0.43814 (7)0.0210 (3)
O20.16249 (13)0.00003 (15)0.51896 (7)0.0223 (3)
O30.14576 (13)0.22260 (14)0.55118 (7)0.0203 (3)
O100.30392 (13)0.09722 (15)0.52817 (7)0.0229 (3)
N110.08612 (15)0.17835 (18)0.53053 (9)0.0185 (3)
H110.112 (2)0.205 (3)0.5749 (14)0.026 (6)*
C10.10110 (18)0.1537 (2)0.42303 (10)0.0181 (4)
C20.04967 (17)0.2267 (2)0.49631 (10)0.0177 (4)
H20.03730.32230.48300.021*
C30.23863 (18)0.1106 (2)0.54311 (11)0.0218 (4)
C40.36889 (18)0.1414 (2)0.48717 (12)0.0263 (5)
H4A0.39820.05910.45910.032*
H4B0.44660.16820.51620.032*
C50.34649 (19)0.2507 (2)0.43025 (11)0.0255 (4)
H5A0.32770.33500.45840.031*
H5B0.43520.26240.39650.031*
C60.1824 (2)0.3593 (2)0.34533 (11)0.0246 (4)
H60.14770.42080.38760.029*
C70.0624 (2)0.3357 (2)0.29766 (11)0.0282 (5)
H7A0.03110.42230.27910.034*
H7B0.09730.28140.25300.034*
C80.0629 (2)0.2655 (2)0.34086 (11)0.0241 (4)
H8A0.10450.32350.38250.029*
H8B0.13530.24900.30640.029*
C90.14019 (19)0.0564 (2)0.41805 (10)0.0197 (4)
H90.10290.03450.42700.024*
C100.18336 (18)0.1151 (2)0.49567 (10)0.0193 (4)
C110.22729 (19)0.2280 (2)0.38059 (11)0.0218 (4)
H11A0.26590.16950.33770.026*
C120.01905 (18)0.1331 (2)0.37367 (10)0.0197 (4)
H120.01840.07580.33000.024*
C130.2729 (2)0.0746 (2)0.62168 (12)0.0300 (5)
H13A0.18690.04680.65280.045*
H13B0.34110.00160.61820.045*
H13C0.31290.15230.64480.045*
C140.3053 (2)0.4275 (3)0.29779 (13)0.0332 (5)
H14A0.27090.50580.27270.050*
H14B0.37550.45510.33070.050*
H14C0.34820.36530.25950.050*
C150.2678 (2)0.0359 (2)0.37455 (12)0.0291 (5)
H15A0.31570.12110.36990.044*
H15B0.23660.00090.32400.044*
H15C0.33260.02750.40190.044*
O1A0.81813 (12)0.99691 (14)0.98122 (6)0.0179 (3)
O2A0.83624 (13)0.85557 (14)0.96239 (7)0.0189 (3)
O3A0.81395 (12)0.88511 (13)0.83245 (7)0.0164 (3)
O10A0.38942 (12)0.88100 (14)0.91775 (7)0.0208 (3)
N11A0.58533 (15)0.91491 (18)0.86173 (9)0.0170 (3)
H11B0.569 (2)0.839 (3)0.8393 (13)0.025 (6)*
C1A0.76808 (17)1.07386 (19)0.91388 (9)0.0149 (4)
C2A0.71516 (17)0.98276 (19)0.84849 (10)0.0153 (4)
H2A0.69441.03930.80230.018*
C3A0.90985 (18)0.8486 (2)0.89763 (10)0.0184 (4)
C4A1.03800 (18)0.9410 (2)0.90419 (11)0.0216 (4)
H4AA1.07110.95380.95850.026*
H4AB1.11440.89670.88050.026*
C5A1.01141 (18)1.0771 (2)0.86762 (11)0.0206 (4)
H5AA0.99111.06410.81230.025*
H5AB1.09931.12940.87650.025*
C6A0.84479 (19)1.2720 (2)0.83779 (10)0.0199 (4)
H6A0.81061.22930.78830.024*
C7A0.7233 (2)1.3519 (2)0.86383 (11)0.0236 (4)
H7AA0.69071.41810.82440.028*
H7AB0.75701.40100.91070.028*
C8A0.59940 (19)1.2629 (2)0.87903 (11)0.0215 (4)
H8AA0.52421.31810.89690.026*
H8AB0.56071.21850.83150.026*
C9A0.53028 (18)1.0664 (2)0.96248 (10)0.0184 (4)
H9A0.56811.02831.01260.022*
C10A0.49670 (17)0.9490 (2)0.91108 (10)0.0174 (4)
C11A0.89160 (17)1.1607 (2)0.89452 (10)0.0172 (4)
H11C0.93091.20520.94260.021*
C12A0.64707 (17)1.1581 (2)0.93868 (10)0.0168 (4)
H12A0.68621.20750.98520.020*
C13A0.9415 (2)0.7027 (2)0.88912 (11)0.0230 (4)
H13D0.85660.65050.89410.035*
H13E1.01600.67600.92860.035*
H13F0.97240.68690.83920.035*
C14A0.9675 (2)1.3635 (2)0.82478 (12)0.0271 (4)
H14D1.01211.39620.87360.041*
H14E0.93261.43900.79320.041*
H14F1.03651.31380.79920.041*
C15A0.39547 (19)1.1407 (2)0.97620 (13)0.0294 (5)
H15D0.35151.17780.92830.044*
H15E0.41861.21301.01250.044*
H15F0.33021.07890.99660.044*
O210.41238 (14)0.26565 (17)0.62699 (8)0.0286 (3)
H210.368 (4)0.205 (4)0.595 (2)0.084 (12)*
O220.21229 (13)0.27193 (16)0.68154 (8)0.0249 (3)
O230.31017 (14)0.65994 (15)0.85688 (8)0.0237 (3)
H230.352 (3)0.742 (4)0.8795 (19)0.067 (10)*
O240.51070 (13)0.64800 (15)0.80351 (8)0.0290 (3)
C210.32987 (18)0.3129 (2)0.67523 (11)0.0210 (4)
C220.39656 (19)0.4253 (2)0.72062 (11)0.0215 (4)
H220.48660.45560.71070.026*
C230.33419 (19)0.4837 (2)0.77402 (10)0.0201 (4)
H23A0.24870.44820.78780.024*
C240.39572 (18)0.6052 (2)0.81339 (10)0.0201 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0235 (6)0.0186 (8)0.0215 (6)0.0056 (5)0.0051 (5)0.0009 (5)
O20.0237 (6)0.0209 (8)0.0236 (6)0.0012 (6)0.0083 (5)0.0030 (6)
O30.0169 (6)0.0227 (8)0.0223 (6)0.0005 (5)0.0060 (5)0.0026 (6)
O100.0167 (6)0.0259 (8)0.0260 (7)0.0004 (5)0.0018 (5)0.0051 (6)
N110.0161 (7)0.0234 (9)0.0158 (8)0.0013 (6)0.0011 (6)0.0042 (6)
C10.0174 (8)0.0165 (10)0.0202 (9)0.0041 (7)0.0016 (7)0.0006 (8)
C20.0145 (8)0.0195 (11)0.0194 (8)0.0009 (7)0.0028 (7)0.0013 (8)
C30.0181 (8)0.0180 (11)0.0306 (10)0.0008 (8)0.0083 (7)0.0000 (8)
C40.0158 (8)0.0275 (13)0.0361 (11)0.0023 (8)0.0049 (8)0.0009 (9)
C50.0178 (9)0.0262 (12)0.0315 (10)0.0014 (8)0.0019 (7)0.0016 (9)
C60.0299 (10)0.0217 (11)0.0210 (9)0.0001 (9)0.0024 (8)0.0013 (8)
C70.0370 (11)0.0268 (13)0.0207 (9)0.0029 (9)0.0030 (8)0.0027 (9)
C80.0268 (9)0.0246 (11)0.0216 (9)0.0058 (8)0.0060 (7)0.0010 (8)
C90.0186 (8)0.0196 (11)0.0217 (9)0.0016 (7)0.0053 (7)0.0045 (8)
C100.0178 (8)0.0180 (11)0.0228 (9)0.0040 (7)0.0049 (7)0.0012 (8)
C110.0207 (9)0.0209 (11)0.0228 (9)0.0012 (8)0.0023 (7)0.0025 (8)
C120.0204 (8)0.0202 (11)0.0188 (9)0.0041 (7)0.0035 (7)0.0039 (7)
C130.0282 (10)0.0294 (13)0.0348 (11)0.0036 (9)0.0146 (8)0.0036 (10)
C140.0425 (12)0.0256 (13)0.0287 (10)0.0069 (10)0.0076 (9)0.0017 (9)
C150.0236 (10)0.0375 (14)0.0274 (10)0.0005 (9)0.0081 (8)0.0092 (9)
O1A0.0212 (6)0.0142 (7)0.0180 (6)0.0022 (5)0.0005 (5)0.0022 (5)
O2A0.0221 (6)0.0139 (7)0.0210 (6)0.0024 (5)0.0039 (5)0.0007 (5)
O3A0.0147 (6)0.0157 (7)0.0187 (6)0.0018 (5)0.0013 (5)0.0022 (5)
O10A0.0157 (6)0.0193 (8)0.0279 (7)0.0028 (5)0.0042 (5)0.0018 (6)
N11A0.0143 (7)0.0155 (9)0.0209 (7)0.0023 (6)0.0002 (6)0.0043 (7)
C1A0.0142 (8)0.0141 (10)0.0158 (8)0.0006 (7)0.0011 (6)0.0005 (7)
C2A0.0126 (8)0.0143 (10)0.0193 (8)0.0010 (7)0.0029 (6)0.0004 (7)
C3A0.0153 (8)0.0208 (11)0.0191 (9)0.0035 (7)0.0013 (7)0.0015 (8)
C4A0.0143 (8)0.0241 (11)0.0260 (9)0.0026 (7)0.0012 (7)0.0032 (8)
C5A0.0154 (8)0.0203 (11)0.0266 (9)0.0026 (7)0.0042 (7)0.0037 (8)
C6A0.0216 (9)0.0157 (10)0.0227 (9)0.0032 (8)0.0035 (7)0.0004 (8)
C7A0.0258 (10)0.0158 (11)0.0292 (10)0.0011 (8)0.0033 (8)0.0023 (8)
C8A0.0171 (8)0.0179 (11)0.0289 (9)0.0023 (7)0.0008 (7)0.0005 (8)
C9A0.0147 (8)0.0178 (11)0.0231 (9)0.0018 (7)0.0035 (7)0.0021 (8)
C10A0.0124 (8)0.0187 (11)0.0206 (8)0.0010 (7)0.0001 (6)0.0026 (7)
C11A0.0148 (8)0.0151 (10)0.0219 (9)0.0031 (7)0.0025 (7)0.0032 (8)
C12A0.0139 (8)0.0160 (10)0.0205 (8)0.0008 (7)0.0020 (6)0.0027 (7)
C13A0.0228 (9)0.0193 (11)0.0275 (9)0.0043 (8)0.0048 (7)0.0000 (8)
C14A0.0282 (10)0.0192 (11)0.0356 (11)0.0053 (8)0.0104 (8)0.0011 (9)
C15A0.0176 (9)0.0266 (13)0.0458 (12)0.0031 (8)0.0113 (8)0.0116 (10)
O210.0190 (7)0.0322 (9)0.0349 (8)0.0021 (6)0.0041 (6)0.0135 (7)
O220.0225 (7)0.0272 (8)0.0249 (6)0.0041 (6)0.0026 (5)0.0047 (6)
O230.0232 (6)0.0233 (8)0.0251 (7)0.0049 (6)0.0053 (5)0.0051 (6)
O240.0198 (7)0.0248 (9)0.0430 (8)0.0036 (6)0.0061 (6)0.0099 (7)
C210.0191 (9)0.0208 (11)0.0222 (9)0.0013 (8)0.0017 (7)0.0007 (8)
C220.0175 (8)0.0199 (11)0.0265 (9)0.0012 (8)0.0008 (7)0.0016 (8)
C230.0187 (8)0.0180 (11)0.0229 (9)0.0026 (7)0.0000 (7)0.0024 (8)
C240.0188 (9)0.0186 (11)0.0220 (9)0.0006 (7)0.0017 (7)0.0028 (7)
Geometric parameters (Å, º) top
O1—O21.4735 (18)N11A—H11B0.87 (3)
O1—C11.456 (2)N11A—C2A1.461 (2)
O2—C31.422 (2)N11A—C10A1.332 (2)
O3—C21.415 (2)C1A—C2A1.521 (2)
O3—C31.432 (2)C1A—C11A1.540 (2)
O10—C101.245 (2)C1A—C12A1.540 (2)
N11—H110.84 (3)C2A—H2A1.0000
N11—C21.456 (2)C3A—C4A1.533 (3)
N11—C101.337 (2)C3A—C13A1.508 (3)
C1—C21.527 (2)C4A—H4AA0.9900
C1—C111.543 (3)C4A—H4AB0.9900
C1—C121.538 (2)C4A—C5A1.524 (3)
C2—H21.0000C5A—H5AA0.9900
C3—C41.537 (3)C5A—H5AB0.9900
C3—C131.514 (3)C5A—C11A1.541 (2)
C4—H4A0.9900C6A—H6A1.0000
C4—H4B0.9900C6A—C7A1.529 (3)
C4—C51.525 (3)C6A—C11A1.539 (3)
C5—H5A0.9900C6A—C14A1.531 (3)
C5—H5B0.9900C7A—H7AA0.9900
C5—C111.537 (3)C7A—H7AB0.9900
C6—H61.0000C7A—C8A1.534 (3)
C6—C71.522 (3)C8A—H8AA0.9900
C6—C111.543 (3)C8A—H8AB0.9900
C6—C141.532 (3)C8A—C12A1.528 (3)
C7—H7A0.9900C9A—H9A1.0000
C7—H7B0.9900C9A—C10A1.505 (3)
C7—C81.523 (3)C9A—C12A1.545 (2)
C8—H8A0.9900C9A—C15A1.535 (2)
C8—H8B0.9900C11A—H11C1.0000
C8—C121.531 (3)C12A—H12A1.0000
C9—H91.0000C13A—H13D0.9800
C9—C101.515 (3)C13A—H13E0.9800
C9—C121.535 (3)C13A—H13F0.9800
C9—C151.532 (2)C14A—H14D0.9800
C11—H11A1.0000C14A—H14E0.9800
C12—H121.0000C14A—H14F0.9800
C13—H13A0.9800C15A—H15D0.9800
C13—H13B0.9800C15A—H15E0.9800
C13—H13C0.9800C15A—H15F0.9800
C14—H14A0.9800O21—H210.91 (4)
C14—H14B0.9800O21—C211.319 (2)
C14—H14C0.9800O22—C211.216 (2)
C15—H15A0.9800O23—H230.98 (4)
C15—H15B0.9800O23—C241.310 (2)
C15—H15C0.9800O24—C241.214 (2)
O1A—O2A1.4744 (19)C21—C221.490 (3)
O1A—C1A1.460 (2)C22—H220.9500
O2A—C3A1.418 (2)C22—C231.316 (3)
O3A—C2A1.415 (2)C23—H23A0.9500
O3A—C3A1.443 (2)C23—C241.495 (3)
O10A—C10A1.251 (2)
C1—O1—O2111.57 (13)O1A—C1A—C11A107.08 (13)
C3—O2—O1107.64 (13)O1A—C1A—C12A104.18 (13)
C2—O3—C3113.52 (14)C2A—C1A—C11A111.62 (14)
C2—N11—H11116.2 (16)C2A—C1A—C12A110.68 (13)
C10—N11—H11115.8 (16)C12A—C1A—C11A112.00 (15)
C10—N11—C2126.99 (16)O3A—C2A—N11A108.03 (15)
O1—C1—C2111.33 (15)O3A—C2A—C1A113.51 (13)
O1—C1—C11107.62 (14)O3A—C2A—H2A107.7
O1—C1—C12103.95 (15)N11A—C2A—C1A111.98 (14)
C2—C1—C11110.12 (16)N11A—C2A—H2A107.7
C2—C1—C12111.19 (14)C1A—C2A—H2A107.7
C12—C1—C11112.44 (15)O2A—C3A—O3A108.03 (13)
O3—C2—N11108.79 (14)O2A—C3A—C4A112.05 (15)
O3—C2—C1113.66 (14)O2A—C3A—C13A104.69 (15)
O3—C2—H2107.2O3A—C3A—C4A109.80 (15)
N11—C2—C1112.51 (15)O3A—C3A—C13A106.48 (16)
N11—C2—H2107.2C13A—C3A—C4A115.37 (15)
C1—C2—H2107.2C3A—C4A—H4AA108.6
O2—C3—O3108.10 (13)C3A—C4A—H4AB108.6
O2—C3—C4111.66 (16)H4AA—C4A—H4AB107.6
O2—C3—C13105.32 (16)C5A—C4A—C3A114.69 (14)
O3—C3—C4110.84 (16)C5A—C4A—H4AA108.6
O3—C3—C13106.97 (17)C5A—C4A—H4AB108.6
C13—C3—C4113.61 (16)C4A—C5A—H5AA108.1
C3—C4—H4A108.7C4A—C5A—H5AB108.1
C3—C4—H4B108.7C4A—C5A—C11A116.83 (15)
H4A—C4—H4B107.6H5AA—C5A—H5AB107.3
C5—C4—C3114.21 (15)C11A—C5A—H5AA108.1
C5—C4—H4A108.7C11A—C5A—H5AB108.1
C5—C4—H4B108.7C7A—C6A—H6A107.8
C4—C5—H5A108.2C7A—C6A—C11A111.06 (15)
C4—C5—H5B108.2C7A—C6A—C14A110.75 (17)
C4—C5—C11116.33 (18)C11A—C6A—H6A107.8
H5A—C5—H5B107.4C14A—C6A—H6A107.8
C11—C5—H5A108.2C14A—C6A—C11A111.34 (15)
C11—C5—H5B108.2C6A—C7A—H7AA109.2
C7—C6—H6107.9C6A—C7A—H7AB109.2
C7—C6—C11110.80 (18)C6A—C7A—C8A112.18 (17)
C7—C6—C14110.16 (17)H7AA—C7A—H7AB107.9
C11—C6—H6107.9C8A—C7A—H7AA109.2
C14—C6—H6107.9C8A—C7A—H7AB109.2
C14—C6—C11112.00 (17)C7A—C8A—H8AA109.6
C6—C7—H7A108.9C7A—C8A—H8AB109.6
C6—C7—H7B108.9H8AA—C8A—H8AB108.1
C6—C7—C8113.15 (16)C12A—C8A—C7A110.35 (15)
H7A—C7—H7B107.8C12A—C8A—H8AA109.6
C8—C7—H7A108.9C12A—C8A—H8AB109.6
C8—C7—H7B108.9C10A—C9A—H9A105.8
C7—C8—H8A109.4C10A—C9A—C12A114.43 (15)
C7—C8—H8B109.4C10A—C9A—C15A110.62 (15)
C7—C8—C12111.15 (16)C12A—C9A—H9A105.8
H8A—C8—H8B108.0C15A—C9A—H9A105.8
C12—C8—H8A109.4C15A—C9A—C12A113.64 (16)
C12—C8—H8B109.4O10A—C10A—N11A120.89 (18)
C10—C9—H9106.1O10A—C10A—C9A119.50 (16)
C10—C9—C12112.67 (16)N11A—C10A—C9A119.52 (16)
C10—C9—C15111.14 (15)C1A—C11A—C5A112.24 (16)
C12—C9—H9106.1C1A—C11A—H11C106.7
C15—C9—H9106.1C5A—C11A—H11C106.7
C15—C9—C12114.07 (16)C6A—C11A—C1A112.58 (15)
O10—C10—N11120.80 (17)C6A—C11A—C5A111.42 (15)
O10—C10—C9120.69 (16)C6A—C11A—H11C106.7
N11—C10—C9118.35 (16)C1A—C12A—C9A109.99 (15)
C1—C11—H11A106.9C1A—C12A—H12A106.6
C5—C11—C1112.49 (16)C8A—C12A—C1A110.88 (15)
C5—C11—C6111.45 (17)C8A—C12A—C9A115.63 (15)
C5—C11—H11A106.9C8A—C12A—H12A106.6
C6—C11—C1111.93 (15)C9A—C12A—H12A106.6
C6—C11—H11A106.9C3A—C13A—H13D109.5
C1—C12—H12107.1C3A—C13A—H13E109.5
C8—C12—C1110.77 (16)C3A—C13A—H13F109.5
C8—C12—C9114.12 (15)H13D—C13A—H13E109.5
C8—C12—H12107.1H13D—C13A—H13F109.5
C9—C12—C1110.22 (15)H13E—C13A—H13F109.5
C9—C12—H12107.1C6A—C14A—H14D109.5
C3—C13—H13A109.5C6A—C14A—H14E109.5
C3—C13—H13B109.5C6A—C14A—H14F109.5
C3—C13—H13C109.5H14D—C14A—H14E109.5
H13A—C13—H13B109.5H14D—C14A—H14F109.5
H13A—C13—H13C109.5H14E—C14A—H14F109.5
H13B—C13—H13C109.5C9A—C15A—H15D109.5
C6—C14—H14A109.5C9A—C15A—H15E109.5
C6—C14—H14B109.5C9A—C15A—H15F109.5
C6—C14—H14C109.5H15D—C15A—H15E109.5
H14A—C14—H14B109.5H15D—C15A—H15F109.5
H14A—C14—H14C109.5H15E—C15A—H15F109.5
H14B—C14—H14C109.5C21—O21—H21112 (2)
C9—C15—H15A109.5C24—O23—H23109.9 (19)
C9—C15—H15B109.5O21—C21—C22111.93 (16)
C9—C15—H15C109.5O22—C21—O21124.56 (19)
H15A—C15—H15B109.5O22—C21—C22123.49 (17)
H15A—C15—H15C109.5C21—C22—H22119.1
H15B—C15—H15C109.5C23—C22—C21121.83 (17)
C1A—O1A—O2A111.13 (12)C23—C22—H22119.1
C3A—O2A—O1A108.31 (13)C22—C23—H23A119.5
C2A—O3A—C3A113.24 (13)C22—C23—C24121.02 (17)
C2A—N11A—H11B116.6 (15)C24—C23—H23A119.5
C10A—N11A—H11B115.8 (15)O23—C24—C23112.32 (16)
C10A—N11A—C2A127.12 (17)O24—C24—O23125.09 (19)
O1A—C1A—C2A110.98 (15)O24—C24—C23122.57 (17)
O1—O2—C3—O375.33 (16)O1A—C1A—C2A—O3A53.41 (18)
O1—O2—C3—C446.84 (18)O1A—C1A—C2A—N11A69.25 (17)
O1—O2—C3—C13170.59 (14)O1A—C1A—C11A—C5A67.91 (18)
O1—C1—C2—O351.2 (2)O1A—C1A—C11A—C6A165.41 (14)
O1—C1—C2—N1172.98 (18)O1A—C1A—C12A—C8A169.96 (15)
O1—C1—C11—C567.0 (2)O1A—C1A—C12A—C9A60.88 (17)
O1—C1—C11—C6166.59 (14)O2A—O1A—C1A—C2A14.00 (17)
O1—C1—C12—C8170.02 (14)O2A—O1A—C1A—C11A108.05 (14)
O1—C1—C12—C962.71 (17)O2A—O1A—C1A—C12A133.15 (13)
O2—O1—C1—C213.05 (18)O2A—C3A—C4A—C5A94.82 (19)
O2—O1—C1—C11107.72 (14)O3A—C3A—C4A—C5A25.2 (2)
O2—O1—C1—C12132.84 (13)C1A—O1A—O2A—C3A46.89 (16)
O2—C3—C4—C596.5 (2)C2A—O3A—C3A—O2A33.9 (2)
O3—C3—C4—C524.1 (2)C2A—O3A—C3A—C4A88.58 (17)
C1—O1—O2—C346.95 (16)C2A—O3A—C3A—C13A145.87 (15)
C2—O3—C3—O236.03 (19)C2A—N11A—C10A—O10A178.97 (16)
C2—O3—C3—C486.64 (18)C2A—N11A—C10A—C9A2.4 (3)
C2—O3—C3—C13149.01 (16)C2A—C1A—C11A—C5A53.7 (2)
C2—N11—C10—O10168.54 (19)C2A—C1A—C11A—C6A72.94 (19)
C2—N11—C10—C916.1 (3)C2A—C1A—C12A—C8A70.70 (19)
C2—C1—C11—C554.5 (2)C2A—C1A—C12A—C9A58.46 (19)
C2—C1—C11—C671.88 (19)C3A—O3A—C2A—N11A96.98 (16)
C2—C1—C12—C870.09 (19)C3A—O3A—C2A—C1A27.8 (2)
C2—C1—C12—C957.2 (2)C3A—C4A—C5A—C11A56.1 (2)
C3—O3—C2—N11101.04 (17)C4A—C5A—C11A—C1A34.7 (2)
C3—O3—C2—C125.2 (2)C4A—C5A—C11A—C6A161.99 (15)
C3—C4—C5—C1157.3 (2)C6A—C7A—C8A—C12A57.9 (2)
C4—C5—C11—C134.6 (2)C7A—C6A—C11A—C1A51.3 (2)
C4—C5—C11—C6161.27 (16)C7A—C6A—C11A—C5A178.43 (15)
C6—C7—C8—C1256.4 (2)C7A—C8A—C12A—C1A57.1 (2)
C7—C6—C11—C151.9 (2)C7A—C8A—C12A—C9A176.83 (16)
C7—C6—C11—C5178.85 (16)C10A—N11A—C2A—O3A144.14 (17)
C7—C8—C12—C155.0 (2)C10A—N11A—C2A—C1A18.4 (2)
C7—C8—C12—C9179.94 (16)C10A—C9A—C12A—C1A42.5 (2)
C10—N11—C2—O3149.75 (18)C10A—C9A—C12A—C8A84.0 (2)
C10—N11—C2—C122.9 (3)C11A—C1A—C2A—O3A65.96 (19)
C10—C9—C12—C149.7 (2)C11A—C1A—C2A—N11A171.38 (14)
C10—C9—C12—C875.73 (19)C11A—C1A—C12A—C8A54.57 (19)
C11—C1—C2—O368.1 (2)C11A—C1A—C12A—C9A176.28 (14)
C11—C1—C2—N11167.73 (14)C11A—C6A—C7A—C8A54.6 (2)
C11—C1—C12—C853.9 (2)C12A—C1A—C2A—O3A168.57 (14)
C11—C1—C12—C9178.82 (16)C12A—C1A—C2A—N11A45.9 (2)
C11—C6—C7—C854.4 (2)C12A—C1A—C11A—C5A178.48 (14)
C12—C1—C2—O3166.63 (16)C12A—C1A—C11A—C6A51.8 (2)
C12—C1—C2—N1142.4 (2)C12A—C9A—C10A—O10A168.40 (16)
C12—C1—C11—C5179.11 (16)C12A—C9A—C10A—N11A14.9 (2)
C12—C1—C11—C652.7 (2)C13A—C3A—C4A—C5A145.53 (16)
C12—C9—C10—O10155.53 (18)C14A—C6A—C7A—C8A178.81 (16)
C12—C9—C10—N1129.1 (2)C14A—C6A—C11A—C1A175.24 (15)
C13—C3—C4—C5144.58 (19)C14A—C6A—C11A—C5A57.7 (2)
C14—C6—C7—C8178.86 (18)C15A—C9A—C10A—O10A38.5 (2)
C14—C6—C11—C1175.34 (16)C15A—C9A—C10A—N11A144.86 (18)
C14—C6—C11—C557.7 (2)C15A—C9A—C12A—C1A170.95 (15)
C15—C9—C10—O1026.1 (3)C15A—C9A—C12A—C8A44.4 (2)
C15—C9—C10—N11158.55 (18)O21—C21—C22—C23177.50 (19)
C15—C9—C12—C1177.59 (16)O22—C21—C22—C233.6 (3)
C15—C9—C12—C852.2 (2)C21—C22—C23—C24173.53 (17)
O1A—O2A—C3A—O3A74.54 (16)C22—C23—C24—O23171.06 (18)
O1A—O2A—C3A—C4A46.53 (17)C22—C23—C24—O247.1 (3)
O1A—O2A—C3A—C13A172.27 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O220.84 (3)2.14 (3)2.970 (2)170 (2)
N11A—H11B···O240.87 (3)2.08 (3)2.935 (2)169 (2)
O21—H21···O100.91 (4)1.67 (4)2.573 (2)172 (4)
O23—H23···O10A0.98 (4)1.58 (4)2.550 (2)169 (3)
Geometry of lactam–acid R22(8) heterosynthons in 14 top
CocrystalO10···O21 (Å)N11···O22 (Å)Dihedral angle (°)
12.574 (3) 2.576 (3)3.019 (3) 3.009 (3)25.7 (2) 26.3 (2)
22.542 (2)2.912 (2)38.4 (2)
32.539 (2) 2.549 (2)3.129 (3) 3.038 (3)20.2 (2) 37.8 (2)
42.573 (2) 2.550 (2)2.970 (2) 2.935 (2)41.2 (2) 7.2 (2)
Unit cells for coformers and cocrystals 14, all at 100 K top
CompoundabcαβγVZMol. vol.Reference
11-Azaartemisinin11.71811.7189.48790901201128.13376.0Nisar et al. (2018)
trans-Cinnamic acid5.550417.54277.71619096.3090746.784186.7Howard et al. (2009)
1 11-Aza:Cin9.55510.31811.96491.08110.5294.001100.82550.4This work
Maleic acid6.93410.0617.48190117.5390462.84115.7This work
2 11-Aza:Mal9.621610.402419.69359090901971.14492.8This work
3 11-Aza2:Mal9.78859.996533.7669090903304.04826.0This work
Fumaric acid7.61214.8706.44690111.3090680.06113.3This work
4 11-Aza2:Fum9.57910.05217.7769096.47901700.82850.4This work
Specific volumes for cocrystals 14 at 100 K top
CocrystalAcid Vol.a3)Combined Vol.b3)Cocrystal Vol.c3)Diff. Specific Vol. ΔV (Å3)
1 11-Aza:Cin186.7562.7550.4-12.3 (-2.2%)
2 11-Aza:Mal115.7491.7492.8+0.9 (+0.2%)
3 11-Aza2:Mal115.7867.7826.0-41.7 (-4.8%)
4 11-Aza2:Fum113.3865.3850.4-14.9 (-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 14.
 

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