Azetidin-2-ones: structures of anti­mitotic compounds based on the 1-(3,4,5-tri­meth­oxy­phen­yl)azetidin-2-one core

Twamley, B.; O'Boyle, N.M.; Meegan, M.J.

doi:10.1107/S2056989020008555

Azetidin-2-ones: structures of antimitotic compounds based on the 1-(3,4,5-trimethoxyphenyl)azetidin-2-one core

B. Twamley, N. M. O'Boyle and M. J. Meegan

Five azetidin-2-ones are described based on the 1-(3,4,5-trimethoxyphenyl)azetidin-2-one core with different substituents on the lactam 3 and 4 positions: (1) 3-(4-fluorophenyl)-4-(4-methoxyphenyl); (2) 3-(furan-2-yl)-4-(4-methoxyphenyl); (3) 3-(naphthalen-1-yl)-4-(4-methoxyphenyl); (4) 3-(3,4-dimethoxyphenyl)-4-(4-methoxyphenyl); (5) 4,4-bis(4-methoxyphenyl)-3-phenyl-1-(3,4,5-trimethoxyphenyl)azetidin-2-one.

Keywords: β-Lactam; antimitotic; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020008555/zl2789sup1.cif Contains datablocks 1, 2, 3, 4, 5, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020008555/zl27891sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020008555/zl27892sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020008555/zl27893sup4.hkl Contains datablock 3
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020008555/zl27894sup5.hkl Contains datablock 4
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020008555/zl27895sup6.hkl Contains datablock 5
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020008555/zl27891sup7.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020008555/zl27892sup8.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020008555/zl27893sup9.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020008555/zl27894sup10.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020008555/zl27895sup11.cml Supplementary material
	Tagged Image Format File (TIF) image https://doi.org/10.1107/S2056989020008555/zl2789sup12.tif Overlay of 1 and PUKNUH with overlay centres N1 C3 and O17/O3 and all oxygen atoms labelled, showing the difference in the B ring orientation. The para-methoxy substituent is also flipped. The C and D ring orientations are similar.
	Tagged Image Format File (TIF) image https://doi.org/10.1107/S2056989020008555/zl2789sup13.tif Overlay with inversion of each unique molecule in the asymmetric unit of 2, showing the difference in the D ring orientations and para-methoxy groups as well as the rotation of the D ring (furan).
	Tagged Image Format File (TIF) image https://doi.org/10.1107/S2056989020008555/zl2789sup14.tif Overlay with inversion of each unique molecule in the asymmetric unit of 5, showing the difference in the B ring orientations, and C' ring para-methoxy group differences.

CCDC references: 2012288; 2012287; 2012286; 2012285; 2012284

checkCIF report

Key indicators

Structure: 1

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.054
wR factor = 0.123
Data-to-parameter ratio = 23.4

Structure: 2

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.056
wR factor = 0.112
Data-to-parameter ratio = 14.7

Structure: 3

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.060
wR factor = 0.188
Data-to-parameter ratio = 13.7

Structure: 4

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.045
wR factor = 0.106
Data-to-parameter ratio = 17.5

Structure: 5

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.045
wR factor = 0.137
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT220_ALERT_2_C NonSolvent Resd 1  C   Ueq(max) / Ueq(min) Range        3.1 Ratio
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.466 Check

Alert level G
PLAT432_ALERT_2_G Short Inter X...Y Contact  F1       ..C25              2.95 Ang.
                                           3/2-x,1-y,-1/2+z  =      2_664 Check
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          R Verify
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         12 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     14.349 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.953 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         47 Report

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O27            106.4 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O27A           106.5 Degree
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C3A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C4A         (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         48 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         13 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 3


Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         68 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 4


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O17      --C2       .        5.2 s.u.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT721_ALERT_1_G Bond    Calc     0.99000, Rep     0.95000 Dev...       0.04 Ang.
              C10      -H10             1.555   1.555 ........     #   21 Check
PLAT725_ALERT_2_G D-H     Calc     0.99000, Rep     0.95000 Dev...       0.04 Ang.
              C10      -H10             1.555   1.555 ........     #   67 Check
PLAT726_ALERT_2_G H...A   Calc     2.44000, Rep     2.46000 Dev...       0.02 Ang.
              H10      -O17             1.555   1.555 ........     #   67 Check
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: 5


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19      ..O17      .       2.63 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         36 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C3A         (Centro SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        125 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         11 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

For all structures, data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3-(4-Fluorophenyl)-4-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (1) top

Crystal data top

C₂₅H₂₄FNO₅	D_x = 1.352 Mg m⁻³
M_r = 437.45	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 3522 reflections
a = 18.6879 (16) Å	θ = 3.1–31.0°
b = 9.4736 (8) Å	µ = 0.10 mm⁻¹
c = 24.283 (2) Å	T = 100 K
V = 4299.1 (6) Å³	Block, clear colourless
Z = 8	0.38 × 0.12 × 0.06 mm
F(000) = 1840

Data collection top

Bruker APEXII Kappa Duo diffractometer	6857 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	4084 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.089
Detector resolution: 8.33 pixels mm^-1	θ_max = 31.0°, θ_min = 1.7°
ω and φ scans	h = −26→21
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −13→13
T_min = 0.689, T_max = 0.746	l = −35→35
36881 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0465P)² + 1.1677P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
6857 reflections	Δρ_max = 0.30 e Å⁻³
293 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints

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	U_iso*/U_eq
C2	0.47067 (9)	0.32435 (16)	0.69423 (6)	0.0167 (3)
C3	0.54877 (9)	0.34631 (16)	0.67672 (6)	0.0168 (3)
H3	0.574487	0.253748	0.676899	0.020*
C4	0.55863 (9)	0.42137 (16)	0.73381 (6)	0.0161 (3)
H4	0.567673	0.524850	0.729603	0.019*
C5	0.44073 (9)	0.39639 (16)	0.79263 (6)	0.0157 (3)
C6	0.47056 (9)	0.46256 (16)	0.83827 (6)	0.0168 (3)
H6	0.516056	0.506887	0.835923	0.020*
C7	0.43227 (9)	0.46254 (16)	0.88764 (6)	0.0183 (3)
C8	0.36475 (9)	0.40188 (17)	0.89083 (6)	0.0192 (3)
C9	0.33578 (9)	0.33638 (16)	0.84420 (7)	0.0182 (3)
C10	0.37356 (9)	0.33370 (16)	0.79465 (7)	0.0176 (3)
H10	0.353756	0.289893	0.762935	0.021*
C12	0.53206 (11)	0.5642 (2)	0.93492 (7)	0.0284 (4)
H12A	0.536811	0.643948	0.909487	0.043*
H12B	0.563192	0.486916	0.922824	0.043*
H12C	0.545983	0.593991	0.972046	0.043*
C14	0.28311 (14)	0.5105 (2)	0.95034 (10)	0.0469 (6)
H14A	0.249823	0.520605	0.919411	0.070*
H14B	0.311537	0.596888	0.954079	0.070*
H14C	0.256060	0.494181	0.984326	0.070*
C16	0.24554 (10)	0.18401 (19)	0.80868 (7)	0.0253 (4)
H16A	0.239028	0.237693	0.774552	0.038*
H16B	0.199815	0.141896	0.819672	0.038*
H16C	0.280870	0.109139	0.802677	0.038*
C18	0.60855 (9)	0.35478 (16)	0.77494 (6)	0.0153 (3)
C19	0.65897 (9)	0.43381 (16)	0.80287 (7)	0.0192 (3)
H19	0.664258	0.531044	0.794202	0.023*
C20	0.70236 (9)	0.37431 (17)	0.84352 (7)	0.0200 (3)
H20	0.737438	0.429973	0.861693	0.024*
C21	0.69374 (9)	0.23316 (17)	0.85708 (7)	0.0181 (3)
C22	0.64337 (9)	0.15142 (17)	0.82885 (7)	0.0203 (4)
H22	0.637915	0.054211	0.837481	0.024*
C23	0.60168 (9)	0.21209 (16)	0.78851 (7)	0.0183 (3)
H23	0.567589	0.155813	0.769535	0.022*
C25	0.78712 (10)	0.24316 (19)	0.92421 (7)	0.0245 (4)
H25A	0.822515	0.272413	0.896703	0.037*
H25B	0.810239	0.183185	0.951859	0.037*
H25C	0.767008	0.326872	0.942168	0.037*
C26	0.56251 (9)	0.42157 (17)	0.62316 (6)	0.0172 (3)
C27	0.59598 (10)	0.34916 (19)	0.58044 (7)	0.0248 (4)
H27	0.612957	0.255969	0.586601	0.030*
C28	0.60505 (11)	0.4109 (2)	0.52881 (7)	0.0290 (4)
H28	0.627489	0.360816	0.499640	0.035*
C29	0.58074 (10)	0.54535 (19)	0.52142 (7)	0.0230 (4)
C30	0.54810 (11)	0.62143 (18)	0.56226 (7)	0.0249 (4)
H30	0.532024	0.715082	0.555723	0.030*
C31	0.53903 (10)	0.55855 (17)	0.61345 (7)	0.0222 (4)
H31	0.516475	0.609864	0.642231	0.027*
F1	0.58878 (6)	0.60640 (12)	0.47102 (4)	0.0335 (3)
N1	0.48152 (7)	0.39025 (13)	0.74384 (5)	0.0150 (3)
O11	0.45909 (7)	0.51679 (12)	0.93550 (5)	0.0235 (3)
O13	0.32920 (7)	0.39465 (13)	0.94054 (5)	0.0252 (3)
O15	0.27020 (6)	0.27641 (12)	0.85124 (5)	0.0243 (3)
O17	0.41799 (7)	0.26893 (12)	0.67469 (5)	0.0217 (3)
O24	0.73096 (7)	0.16568 (12)	0.89773 (5)	0.0237 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0231 (9)	0.0135 (7)	0.0133 (7)	0.0008 (7)	−0.0001 (6)	0.0001 (6)
C3	0.0209 (9)	0.0144 (7)	0.0151 (7)	−0.0005 (6)	0.0017 (6)	−0.0012 (6)
C4	0.0190 (9)	0.0150 (7)	0.0143 (7)	−0.0002 (6)	0.0003 (6)	0.0000 (6)
C5	0.0210 (9)	0.0127 (7)	0.0134 (7)	0.0027 (6)	0.0016 (6)	0.0016 (5)
C6	0.0219 (9)	0.0137 (7)	0.0149 (7)	−0.0016 (6)	0.0008 (6)	0.0017 (6)
C7	0.0285 (10)	0.0135 (7)	0.0129 (7)	0.0017 (7)	−0.0021 (6)	0.0005 (6)
C8	0.0244 (10)	0.0193 (8)	0.0139 (7)	0.0031 (7)	0.0040 (6)	0.0024 (6)
C9	0.0197 (9)	0.0160 (7)	0.0190 (8)	0.0019 (7)	0.0012 (7)	0.0021 (6)
C10	0.0206 (9)	0.0161 (7)	0.0161 (7)	0.0017 (7)	−0.0010 (6)	−0.0008 (6)
C12	0.0356 (12)	0.0353 (10)	0.0144 (8)	−0.0139 (9)	−0.0030 (7)	0.0014 (7)
C14	0.0583 (16)	0.0337 (11)	0.0487 (14)	0.0113 (11)	0.0362 (12)	0.0062 (10)
C16	0.0219 (10)	0.0296 (9)	0.0246 (9)	−0.0051 (8)	−0.0005 (7)	−0.0007 (7)
C18	0.0164 (8)	0.0149 (7)	0.0146 (7)	−0.0008 (6)	0.0019 (6)	−0.0009 (6)
C19	0.0224 (9)	0.0136 (7)	0.0217 (8)	−0.0011 (7)	−0.0001 (7)	−0.0002 (6)
C20	0.0185 (9)	0.0196 (8)	0.0217 (8)	−0.0018 (7)	−0.0019 (7)	−0.0039 (6)
C21	0.0183 (9)	0.0182 (8)	0.0178 (7)	0.0028 (7)	−0.0013 (6)	−0.0017 (6)
C22	0.0239 (10)	0.0132 (7)	0.0238 (8)	0.0001 (7)	−0.0022 (7)	0.0009 (6)
C23	0.0196 (9)	0.0156 (7)	0.0197 (8)	−0.0032 (7)	−0.0022 (7)	−0.0016 (6)
C25	0.0220 (9)	0.0302 (9)	0.0212 (8)	0.0001 (8)	−0.0061 (7)	−0.0016 (7)
C26	0.0171 (9)	0.0188 (7)	0.0156 (7)	−0.0030 (7)	−0.0003 (6)	0.0004 (6)
C27	0.0307 (11)	0.0235 (8)	0.0202 (8)	0.0047 (8)	0.0061 (7)	0.0013 (7)
C28	0.0327 (11)	0.0356 (10)	0.0189 (8)	0.0024 (9)	0.0098 (8)	0.0019 (7)
C29	0.0246 (10)	0.0286 (9)	0.0157 (8)	−0.0094 (8)	−0.0011 (7)	0.0058 (7)
C30	0.0363 (12)	0.0182 (8)	0.0204 (8)	−0.0045 (8)	−0.0058 (8)	0.0025 (6)
C31	0.0299 (10)	0.0194 (8)	0.0172 (8)	−0.0001 (7)	0.0006 (7)	−0.0033 (6)
F1	0.0410 (7)	0.0405 (6)	0.0190 (5)	−0.0099 (5)	0.0026 (5)	0.0107 (5)
N1	0.0162 (7)	0.0160 (6)	0.0129 (6)	−0.0001 (5)	0.0001 (5)	−0.0011 (5)
O11	0.0323 (7)	0.0257 (6)	0.0126 (5)	−0.0068 (6)	0.0003 (5)	−0.0012 (4)
O13	0.0322 (8)	0.0275 (6)	0.0160 (6)	0.0033 (6)	0.0087 (5)	0.0018 (5)
O15	0.0206 (7)	0.0290 (6)	0.0235 (6)	−0.0041 (5)	0.0043 (5)	−0.0026 (5)
O17	0.0236 (7)	0.0242 (6)	0.0173 (6)	−0.0049 (5)	−0.0002 (5)	−0.0040 (5)
O24	0.0255 (7)	0.0205 (6)	0.0252 (6)	0.0005 (5)	−0.0091 (5)	0.0008 (5)

Geometric parameters (Å, º) top

C2—C3	1.534 (2)	C16—H16B	0.9800
C2—N1	1.3719 (19)	C16—H16C	0.9800
C2—O17	1.213 (2)	C16—O15	1.431 (2)
C3—H3	1.0000	C18—C19	1.381 (2)
C3—C4	1.569 (2)	C18—C23	1.397 (2)
C3—C26	1.505 (2)	C19—H19	0.9500
C4—H4	1.0000	C19—C20	1.396 (2)
C4—C18	1.505 (2)	C20—H20	0.9500
C4—N1	1.491 (2)	C20—C21	1.387 (2)
C5—C6	1.390 (2)	C21—C22	1.399 (2)
C5—C10	1.390 (2)	C21—O24	1.366 (2)
C5—N1	1.410 (2)	C22—H22	0.9500
C6—H6	0.9500	C22—C23	1.377 (2)
C6—C7	1.396 (2)	C23—H23	0.9500
C7—C8	1.389 (2)	C25—H25A	0.9800
C7—O11	1.3659 (19)	C25—H25B	0.9800
C8—C9	1.400 (2)	C25—H25C	0.9800
C8—O13	1.3796 (19)	C25—O24	1.433 (2)
C9—C10	1.395 (2)	C26—C27	1.392 (2)
C9—O15	1.362 (2)	C26—C31	1.390 (2)
C10—H10	0.9500	C27—H27	0.9500
C12—H12A	0.9800	C27—C28	1.394 (2)
C12—H12B	0.9800	C28—H28	0.9500
C12—H12C	0.9800	C28—C29	1.364 (3)
C12—O11	1.436 (2)	C29—C30	1.369 (3)
C14—H14A	0.9800	C29—F1	1.3619 (19)
C14—H14B	0.9800	C30—H30	0.9500
C14—H14C	0.9800	C30—C31	1.389 (2)
C14—O13	1.415 (2)	C31—H31	0.9500
C16—H16A	0.9800

N1—C2—C3	92.36 (12)	O15—C16—H16C	109.5
O17—C2—C3	136.27 (14)	C19—C18—C4	121.42 (13)
O17—C2—N1	131.35 (15)	C19—C18—C23	118.12 (15)
C2—C3—H3	109.7	C23—C18—C4	120.33 (14)
C2—C3—C4	85.89 (11)	C18—C19—H19	119.2
C4—C3—H3	109.7	C18—C19—C20	121.62 (15)
C26—C3—C2	117.77 (14)	C20—C19—H19	119.2
C26—C3—H3	109.7	C19—C20—H20	120.3
C26—C3—C4	121.92 (13)	C21—C20—C19	119.33 (15)
C3—C4—H4	112.0	C21—C20—H20	120.3
C18—C4—C3	117.98 (13)	C20—C21—C22	119.71 (15)
C18—C4—H4	112.0	O24—C21—C20	124.32 (15)
N1—C4—C3	86.63 (11)	O24—C21—C22	115.96 (14)
N1—C4—H4	112.0	C21—C22—H22	120.1
N1—C4—C18	114.06 (13)	C23—C22—C21	119.90 (15)
C6—C5—N1	118.15 (15)	C23—C22—H22	120.1
C10—C5—C6	121.79 (14)	C18—C23—H23	119.4
C10—C5—N1	120.03 (14)	C22—C23—C18	121.29 (15)
C5—C6—H6	120.7	C22—C23—H23	119.4
C5—C6—C7	118.62 (16)	H25A—C25—H25B	109.5
C7—C6—H6	120.7	H25A—C25—H25C	109.5
C8—C7—C6	120.90 (15)	H25B—C25—H25C	109.5
O11—C7—C6	122.84 (16)	O24—C25—H25A	109.5
O11—C7—C8	116.22 (14)	O24—C25—H25B	109.5
C7—C8—C9	119.32 (15)	O24—C25—H25C	109.5
O13—C8—C7	120.45 (15)	C27—C26—C3	119.15 (15)
O13—C8—C9	119.97 (15)	C31—C26—C3	122.34 (15)
C10—C9—C8	120.65 (16)	C31—C26—C27	118.40 (15)
O15—C9—C8	115.56 (14)	C26—C27—H27	119.4
O15—C9—C10	123.79 (15)	C26—C27—C28	121.21 (16)
C5—C10—C9	118.68 (15)	C28—C27—H27	119.4
C5—C10—H10	120.7	C27—C28—H28	121.0
C9—C10—H10	120.7	C29—C28—C27	118.00 (17)
H12A—C12—H12B	109.5	C29—C28—H28	121.0
H12A—C12—H12C	109.5	C28—C29—C30	122.99 (16)
H12B—C12—H12C	109.5	F1—C29—C28	118.56 (16)
O11—C12—H12A	109.5	F1—C29—C30	118.45 (16)
O11—C12—H12B	109.5	C29—C30—H30	120.8
O11—C12—H12C	109.5	C29—C30—C31	118.47 (16)
H14A—C14—H14B	109.5	C31—C30—H30	120.8
H14A—C14—H14C	109.5	C26—C31—H31	119.5
H14B—C14—H14C	109.5	C30—C31—C26	120.91 (16)
O13—C14—H14A	109.5	C30—C31—H31	119.5
O13—C14—H14B	109.5	C2—N1—C4	95.12 (12)
O13—C14—H14C	109.5	C2—N1—C5	132.59 (14)
H16A—C16—H16B	109.5	C5—N1—C4	130.67 (13)
H16A—C16—H16C	109.5	C7—O11—C12	117.25 (13)
H16B—C16—H16C	109.5	C8—O13—C14	113.68 (14)
O15—C16—H16A	109.5	C9—O15—C16	117.04 (13)
O15—C16—H16B	109.5	C21—O24—C25	117.21 (13)

C2—C3—C4—C18	115.73 (14)	C18—C4—N1—C5	47.2 (2)
C2—C3—C4—N1	0.19 (11)	C18—C19—C20—C21	−1.4 (3)
C2—C3—C26—C27	−116.12 (17)	C19—C18—C23—C22	0.5 (2)
C2—C3—C26—C31	59.8 (2)	C19—C20—C21—C22	1.9 (3)
C3—C2—N1—C4	0.22 (12)	C19—C20—C21—O24	−177.04 (16)
C3—C2—N1—C5	−165.98 (16)	C20—C21—C22—C23	−1.2 (3)
C3—C4—C18—C19	133.10 (16)	C20—C21—O24—C25	−6.2 (2)
C3—C4—C18—C23	−51.2 (2)	C21—C22—C23—C18	0.0 (3)
C3—C4—N1—C2	−0.21 (12)	C22—C21—O24—C25	174.84 (15)
C3—C4—N1—C5	166.40 (15)	C23—C18—C19—C20	0.1 (2)
C3—C26—C27—C28	175.17 (17)	C26—C3—C4—C18	−123.90 (17)
C3—C26—C31—C30	−175.38 (16)	C26—C3—C4—N1	120.56 (15)
C4—C3—C26—C27	140.43 (17)	C26—C27—C28—C29	0.6 (3)
C4—C3—C26—C31	−43.6 (2)	C27—C26—C31—C30	0.6 (3)
C4—C18—C19—C20	175.95 (15)	C27—C28—C29—C30	0.0 (3)
C4—C18—C23—C22	−175.32 (15)	C27—C28—C29—F1	−179.49 (16)
C5—C6—C7—C8	−2.1 (2)	C28—C29—C30—C31	−0.3 (3)
C5—C6—C7—O11	175.69 (14)	C29—C30—C31—C26	0.0 (3)
C6—C5—C10—C9	−0.7 (2)	C31—C26—C27—C28	−0.9 (3)
C6—C5—N1—C2	173.83 (15)	F1—C29—C30—C31	179.16 (16)
C6—C5—N1—C4	12.1 (2)	N1—C2—C3—C4	−0.20 (11)
C6—C7—C8—C9	1.9 (2)	N1—C2—C3—C26	−124.35 (14)
C6—C7—C8—O13	175.99 (14)	N1—C4—C18—C19	−127.44 (16)
C6—C7—O11—C12	−5.4 (2)	N1—C4—C18—C23	48.3 (2)
C7—C8—C9—C10	−1.0 (2)	N1—C5—C6—C7	−176.57 (14)
C7—C8—C9—O15	178.35 (14)	N1—C5—C10—C9	177.32 (14)
C7—C8—O13—C14	92.8 (2)	O11—C7—C8—C9	−176.06 (14)
C8—C7—O11—C12	172.48 (14)	O11—C7—C8—O13	−1.9 (2)
C8—C9—C10—C5	0.5 (2)	O13—C8—C9—C10	−175.20 (14)
C8—C9—O15—C16	−167.28 (15)	O13—C8—C9—O15	4.2 (2)
C9—C8—O13—C14	−93.2 (2)	O15—C9—C10—C5	−178.86 (14)
C10—C5—C6—C7	1.5 (2)	O17—C2—C3—C4	−178.65 (19)
C10—C5—N1—C2	−4.3 (3)	O17—C2—C3—C26	57.2 (3)
C10—C5—N1—C4	−166.05 (14)	O17—C2—N1—C4	178.78 (17)
C10—C9—O15—C16	12.1 (2)	O17—C2—N1—C5	12.6 (3)
C18—C4—N1—C2	−119.45 (13)	O24—C21—C22—C23	177.78 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O17	0.95	2.46	3.091 (2)	123
C12—H12C···O11ⁱ	0.98	2.48	3.243 (2)	135

Symmetry code: (i) −x+1, −y+1, −z+2.

3-(Furan-2-yl)-4-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (2) top

Crystal data top

C₂₃H₂₃NO₆	F(000) = 1728
M_r = 409.42	D_x = 1.323 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.794 (2) Å	Cell parameters from 9712 reflections
b = 9.1396 (9) Å	θ = 2.2–26.1°
c = 23.161 (2) Å	µ = 0.10 mm⁻¹
β = 101.0705 (18)°	T = 100 K
V = 4112.0 (7) Å³	Block, colourless
Z = 8	0.42 × 0.3 × 0.04 mm

Data collection top

Bruker APEXII Kappa Duo diffractometer	8072 independent reflections
Radiation source: standard sealed X-ray tube, Siemens, KFF Mo 2K -90 C	5950 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 8.33 pixels mm^-1	θ_max = 26.1°, θ_min = 1.8°
ω and φ scans	h = −24→24
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −11→11
T_min = 0.660, T_max = 0.745	l = −28→28
104383 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.056	w = 1/[σ²(F_o²) + (0.0339P)² + 3.2926P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.112	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.25 e Å⁻³
8072 reflections	Δρ_min = −0.25 e Å⁻³
550 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00110 (18)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C2	0.47248 (11)	0.3915 (2)	0.20698 (9)	0.0191 (4)
C3	0.54420 (10)	0.3731 (2)	0.19170 (9)	0.0197 (4)
H3	0.567145	0.469890	0.189674	0.024*
C4	0.56531 (10)	0.3031 (2)	0.25452 (9)	0.0192 (4)
H4	0.573621	0.195483	0.252203	0.023*
C5	0.46055 (10)	0.3049 (2)	0.30884 (9)	0.0190 (4)
C6	0.49630 (10)	0.2258 (2)	0.35596 (9)	0.0186 (4)
H6	0.542512	0.196365	0.356850	0.022*
C7	0.46335 (11)	0.1905 (2)	0.40192 (9)	0.0200 (5)
C8	0.39586 (11)	0.2346 (2)	0.40053 (9)	0.0219 (5)
C9	0.36241 (10)	0.3206 (2)	0.35366 (9)	0.0226 (5)
C10	0.39389 (10)	0.3545 (2)	0.30683 (9)	0.0208 (5)
H10	0.370564	0.410008	0.274372	0.025*
C12	0.56294 (11)	0.0660 (2)	0.45217 (10)	0.0265 (5)
H12A	0.592766	0.151371	0.451573	0.040*
H12B	0.564784	0.003971	0.417994	0.040*
H12C	0.578719	0.010074	0.488339	0.040*
C14	0.36424 (13)	0.2922 (3)	0.49058 (10)	0.0351 (6)
H14A	0.412296	0.307489	0.509826	0.053*
H14B	0.338187	0.254135	0.519289	0.053*
H14C	0.344203	0.385328	0.474793	0.053*
C16	0.26548 (12)	0.4684 (3)	0.31493 (11)	0.0346 (6)
H16A	0.294965	0.554720	0.315525	0.052*
H16B	0.221075	0.497658	0.324055	0.052*
H16C	0.258105	0.423415	0.275804	0.052*
C18	0.62031 (10)	0.3758 (2)	0.29826 (9)	0.0190 (4)
C19	0.61448 (10)	0.5225 (2)	0.31302 (9)	0.0220 (5)
H19	0.575634	0.577145	0.294165	0.026*
C20	0.66395 (11)	0.5896 (2)	0.35439 (10)	0.0240 (5)
H20	0.658855	0.689345	0.364289	0.029*
C21	0.72133 (11)	0.5111 (2)	0.38163 (9)	0.0230 (5)
C22	0.72891 (11)	0.3664 (2)	0.36712 (10)	0.0267 (5)
H22	0.768502	0.312916	0.385176	0.032*
C23	0.67788 (11)	0.2997 (2)	0.32570 (10)	0.0248 (5)
H23	0.682772	0.199631	0.316130	0.030*
C25	0.83308 (12)	0.5203 (3)	0.44327 (11)	0.0376 (6)
H25A	0.862093	0.586967	0.470516	0.056*
H25B	0.854927	0.500759	0.409499	0.056*
H25C	0.827427	0.428161	0.463481	0.056*
C26	0.54927 (10)	0.2819 (2)	0.14043 (9)	0.0204 (5)
C28	0.52460 (12)	0.0841 (2)	0.08710 (10)	0.0274 (5)
H28	0.506039	−0.008412	0.073696	0.033*
C29	0.56570 (11)	0.1641 (2)	0.06038 (10)	0.0276 (5)
H29	0.580973	0.140432	0.025057	0.033*
C30	0.58228 (11)	0.2926 (2)	0.09538 (9)	0.0257 (5)
H30	0.611211	0.370625	0.088044	0.031*
N1	0.49383 (8)	0.33475 (18)	0.26178 (7)	0.0186 (4)
O11	0.49377 (7)	0.11359 (16)	0.45011 (6)	0.0243 (3)
O13	0.36136 (7)	0.18958 (17)	0.44377 (6)	0.0274 (4)
O15	0.29799 (7)	0.36539 (18)	0.35776 (7)	0.0299 (4)
O17	0.41698 (7)	0.43656 (16)	0.18205 (6)	0.0233 (3)
O24	0.76701 (7)	0.58592 (17)	0.42327 (7)	0.0283 (4)
O27	0.51283 (7)	0.15338 (16)	0.13638 (6)	0.0262 (4)
C2A	0.01341 (11)	0.9003 (2)	0.19312 (10)	0.0235 (5)
C3A	−0.06450 (10)	0.8773 (2)	0.17615 (9)	0.0238 (5)
H3A	−0.089512	0.972865	0.172892	0.029*
C4A	−0.05884 (10)	0.8100 (2)	0.23922 (9)	0.0221 (5)
H4A	−0.064913	0.701345	0.237090	0.027*
C5A	0.06718 (10)	0.8324 (2)	0.29907 (9)	0.0222 (5)
C6A	0.05023 (11)	0.7687 (2)	0.34848 (10)	0.0246 (5)
H6A	0.004496	0.736727	0.348188	0.030*
C7A	0.10090 (11)	0.7520 (2)	0.39857 (10)	0.0263 (5)
C8A	0.16773 (11)	0.7963 (2)	0.39858 (10)	0.0276 (5)
C9A	0.18367 (11)	0.8617 (2)	0.34839 (10)	0.0272 (5)
C10A	0.13357 (10)	0.8799 (2)	0.29815 (10)	0.0243 (5)
H10A	0.144426	0.923947	0.263904	0.029*
C12A	0.01940 (13)	0.6680 (3)	0.45433 (11)	0.0419 (6)
H12D	0.017145	0.638564	0.494599	0.063*
H12E	0.000957	0.589440	0.427025	0.063*
H12F	−0.007888	0.757043	0.444148	0.063*
C14A	0.25700 (12)	0.6580 (3)	0.45336 (11)	0.0379 (6)
H14D	0.285078	0.660480	0.422828	0.057*
H14E	0.226759	0.572192	0.447434	0.057*
H14F	0.287129	0.652246	0.492163	0.057*
C16A	0.26520 (12)	0.9975 (3)	0.30756 (12)	0.0381 (6)
H16D	0.257857	0.942833	0.270470	0.057*
H16E	0.313269	1.029574	0.317547	0.057*
H16F	0.234848	1.083105	0.303271	0.057*
C18A	−0.09903 (10)	0.8755 (2)	0.28105 (9)	0.0214 (5)
C19A	−0.09323 (11)	1.0232 (2)	0.29593 (11)	0.0289 (5)
H19A	−0.064140	1.084194	0.278196	0.035*
C20A	−0.12873 (11)	1.0823 (2)	0.33575 (11)	0.0312 (6)
H20A	−0.124086	1.183340	0.345306	0.037*
C21A	−0.17135 (11)	0.9945 (2)	0.36199 (10)	0.0246 (5)
C22A	−0.17905 (11)	0.8480 (2)	0.34707 (10)	0.0243 (5)
H22A	−0.209307	0.787966	0.363932	0.029*
C23A	−0.14226 (10)	0.7898 (2)	0.30737 (9)	0.0233 (5)
H23A	−0.146783	0.688701	0.297950	0.028*
C25A	−0.25363 (12)	0.9820 (3)	0.42498 (11)	0.0310 (5)
H25D	−0.233899	0.890512	0.442831	0.046*
H25E	−0.292126	0.959781	0.392753	0.046*
H25F	−0.270186	1.041064	0.454722	0.046*
C26A	−0.09111 (11)	0.7821 (2)	0.12535 (10)	0.0250 (5)
C28A	−0.17691 (13)	0.6706 (3)	0.06858 (11)	0.0385 (6)
H28A	−0.222141	0.639372	0.051626	0.046*
C29A	−0.11983 (13)	0.6254 (3)	0.05174 (11)	0.0361 (6)
H29A	−0.116986	0.558946	0.020772	0.043*
C30A	−0.06364 (13)	0.6962 (3)	0.08924 (11)	0.0356 (6)
H30A	−0.016085	0.684579	0.088640	0.043*
N1A	0.01505 (8)	0.84972 (19)	0.24877 (8)	0.0220 (4)
O11A	0.08906 (8)	0.69564 (19)	0.45029 (7)	0.0363 (4)
O13A	0.21642 (8)	0.78714 (19)	0.44995 (7)	0.0371 (4)
O15A	0.25015 (8)	0.90595 (19)	0.35308 (7)	0.0346 (4)
O17A	0.05790 (7)	0.94552 (17)	0.16854 (7)	0.0293 (4)
O24A	−0.20227 (8)	1.06133 (17)	0.40262 (7)	0.0320 (4)
O27A	−0.16117 (8)	0.7684 (2)	0.11372 (7)	0.0379 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0248 (11)	0.0146 (10)	0.0181 (11)	−0.0017 (9)	0.0052 (9)	−0.0009 (9)
C3	0.0215 (11)	0.0187 (10)	0.0193 (11)	0.0014 (8)	0.0051 (9)	0.0039 (9)
C4	0.0223 (11)	0.0178 (10)	0.0193 (11)	0.0023 (8)	0.0084 (9)	0.0037 (9)
C5	0.0231 (11)	0.0171 (10)	0.0174 (11)	−0.0063 (8)	0.0054 (9)	−0.0045 (9)
C6	0.0220 (11)	0.0166 (10)	0.0179 (11)	−0.0029 (8)	0.0052 (9)	−0.0023 (9)
C7	0.0276 (12)	0.0160 (10)	0.0165 (11)	−0.0047 (8)	0.0046 (9)	−0.0017 (9)
C8	0.0258 (12)	0.0240 (11)	0.0174 (11)	−0.0073 (9)	0.0083 (9)	−0.0016 (9)
C9	0.0168 (11)	0.0269 (12)	0.0243 (12)	−0.0059 (9)	0.0047 (9)	−0.0048 (10)
C10	0.0207 (11)	0.0226 (11)	0.0183 (11)	−0.0033 (9)	0.0020 (9)	−0.0005 (9)
C12	0.0312 (12)	0.0304 (12)	0.0183 (12)	0.0048 (10)	0.0060 (9)	0.0039 (10)
C14	0.0405 (14)	0.0417 (15)	0.0264 (13)	−0.0054 (11)	0.0150 (11)	−0.0070 (11)
C16	0.0228 (12)	0.0516 (16)	0.0291 (14)	0.0048 (11)	0.0041 (10)	0.0026 (12)
C18	0.0203 (11)	0.0199 (11)	0.0181 (11)	0.0007 (8)	0.0068 (8)	0.0037 (9)
C19	0.0196 (11)	0.0213 (11)	0.0246 (12)	0.0047 (9)	0.0033 (9)	0.0036 (9)
C20	0.0258 (12)	0.0204 (11)	0.0257 (12)	0.0020 (9)	0.0043 (9)	0.0006 (9)
C21	0.0216 (11)	0.0261 (12)	0.0214 (12)	−0.0035 (9)	0.0042 (9)	0.0044 (9)
C22	0.0227 (11)	0.0255 (12)	0.0306 (13)	0.0058 (9)	0.0018 (10)	0.0084 (10)
C23	0.0283 (12)	0.0194 (11)	0.0271 (12)	0.0047 (9)	0.0067 (10)	0.0044 (9)
C25	0.0261 (13)	0.0438 (15)	0.0379 (15)	0.0004 (11)	−0.0068 (11)	0.0047 (12)
C26	0.0203 (11)	0.0187 (11)	0.0221 (11)	0.0013 (8)	0.0041 (9)	0.0031 (9)
C28	0.0359 (13)	0.0240 (12)	0.0214 (12)	0.0018 (10)	0.0031 (10)	−0.0033 (10)
C29	0.0329 (13)	0.0306 (12)	0.0201 (12)	0.0045 (10)	0.0068 (10)	−0.0005 (10)
C30	0.0271 (12)	0.0287 (12)	0.0229 (12)	−0.0019 (9)	0.0088 (10)	0.0024 (10)
N1	0.0189 (9)	0.0195 (9)	0.0182 (9)	−0.0007 (7)	0.0054 (7)	0.0020 (7)
O11	0.0283 (8)	0.0265 (8)	0.0189 (8)	0.0012 (6)	0.0066 (6)	0.0039 (7)
O13	0.0299 (8)	0.0343 (9)	0.0208 (8)	−0.0075 (7)	0.0116 (7)	0.0000 (7)
O15	0.0195 (8)	0.0453 (10)	0.0254 (9)	−0.0007 (7)	0.0059 (6)	0.0033 (7)
O17	0.0218 (8)	0.0253 (8)	0.0227 (8)	0.0014 (6)	0.0038 (6)	0.0045 (6)
O24	0.0240 (8)	0.0291 (9)	0.0283 (9)	−0.0020 (7)	−0.0037 (7)	0.0040 (7)
O27	0.0327 (9)	0.0227 (8)	0.0252 (9)	−0.0032 (7)	0.0099 (7)	−0.0005 (7)
C2A	0.0229 (11)	0.0211 (11)	0.0263 (13)	0.0016 (9)	0.0048 (10)	−0.0006 (10)
C3A	0.0195 (11)	0.0259 (11)	0.0261 (12)	0.0007 (9)	0.0046 (9)	0.0036 (10)
C4A	0.0181 (11)	0.0226 (11)	0.0245 (12)	−0.0004 (9)	0.0010 (9)	0.0027 (9)
C5A	0.0202 (11)	0.0206 (11)	0.0243 (12)	0.0030 (8)	0.0006 (9)	−0.0029 (9)
C6A	0.0206 (11)	0.0237 (11)	0.0286 (13)	0.0003 (9)	0.0022 (9)	0.0000 (10)
C7A	0.0287 (12)	0.0236 (11)	0.0257 (13)	0.0030 (9)	0.0027 (10)	−0.0003 (10)
C8A	0.0261 (12)	0.0273 (12)	0.0253 (13)	0.0055 (9)	−0.0055 (10)	−0.0045 (10)
C9A	0.0185 (11)	0.0256 (12)	0.0363 (14)	0.0016 (9)	0.0025 (10)	−0.0075 (10)
C10A	0.0203 (11)	0.0251 (11)	0.0279 (12)	0.0022 (9)	0.0057 (9)	−0.0030 (10)
C12A	0.0418 (15)	0.0535 (17)	0.0307 (14)	−0.0064 (13)	0.0075 (12)	0.0085 (13)
C14A	0.0298 (13)	0.0469 (16)	0.0350 (15)	0.0078 (11)	0.0011 (11)	0.0061 (12)
C16A	0.0217 (12)	0.0458 (16)	0.0472 (16)	−0.0046 (11)	0.0072 (11)	−0.0060 (13)
C18A	0.0172 (11)	0.0231 (11)	0.0226 (12)	0.0011 (8)	0.0004 (9)	0.0027 (9)
C19A	0.0262 (12)	0.0230 (12)	0.0398 (14)	−0.0037 (9)	0.0124 (11)	0.0034 (11)
C20A	0.0303 (13)	0.0199 (12)	0.0454 (15)	−0.0003 (9)	0.0122 (11)	−0.0009 (11)
C21A	0.0228 (11)	0.0247 (12)	0.0266 (12)	0.0049 (9)	0.0054 (10)	0.0023 (10)
C22A	0.0235 (11)	0.0246 (11)	0.0250 (12)	−0.0011 (9)	0.0052 (9)	0.0047 (10)
C23A	0.0244 (11)	0.0200 (11)	0.0239 (12)	−0.0022 (9)	0.0008 (9)	0.0008 (9)
C25A	0.0309 (13)	0.0324 (13)	0.0319 (13)	0.0033 (10)	0.0120 (11)	0.0038 (11)
C26A	0.0188 (11)	0.0317 (12)	0.0230 (12)	−0.0008 (9)	0.0005 (9)	0.0063 (10)
C28A	0.0380 (15)	0.0428 (15)	0.0313 (14)	−0.0098 (12)	−0.0016 (11)	−0.0039 (12)
C29A	0.0427 (15)	0.0367 (14)	0.0281 (14)	−0.0022 (12)	0.0048 (11)	−0.0033 (11)
C30A	0.0306 (13)	0.0400 (14)	0.0364 (14)	0.0034 (11)	0.0072 (11)	0.0010 (12)
N1A	0.0162 (9)	0.0255 (10)	0.0237 (10)	0.0004 (7)	0.0021 (7)	0.0016 (8)
O11A	0.0347 (9)	0.0438 (10)	0.0282 (9)	−0.0004 (8)	0.0003 (7)	0.0078 (8)
O13A	0.0313 (9)	0.0430 (10)	0.0317 (9)	0.0080 (8)	−0.0073 (7)	−0.0044 (8)
O15A	0.0191 (8)	0.0415 (10)	0.0409 (10)	−0.0019 (7)	0.0003 (7)	−0.0027 (8)
O17A	0.0227 (8)	0.0339 (9)	0.0322 (9)	−0.0029 (7)	0.0079 (7)	0.0040 (7)
O24A	0.0345 (9)	0.0252 (9)	0.0404 (10)	0.0022 (7)	0.0176 (8)	−0.0011 (7)
O27A	0.0264 (9)	0.0499 (11)	0.0360 (10)	−0.0033 (8)	0.0026 (7)	−0.0075 (8)

Geometric parameters (Å, º) top

C2—C3	1.537 (3)	C2A—C3A	1.531 (3)
C2—N1	1.361 (3)	C2A—N1A	1.364 (3)
C2—O17	1.211 (2)	C2A—O17A	1.209 (3)
C3—H3	1.0000	C3A—H3A	1.0000
C3—C4	1.571 (3)	C3A—C4A	1.569 (3)
C3—C26	1.469 (3)	C3A—C26A	1.477 (3)
C4—H4	1.0000	C4A—H4A	1.0000
C4—C18	1.493 (3)	C4A—C18A	1.492 (3)
C4—N1	1.485 (2)	C4A—N1A	1.482 (3)
C5—C6	1.384 (3)	C5A—C6A	1.382 (3)
C5—C10	1.388 (3)	C5A—C10A	1.388 (3)
C5—N1	1.404 (3)	C5A—N1A	1.409 (3)
C6—H6	0.9500	C6A—H6A	0.9500
C6—C7	1.389 (3)	C6A—C7A	1.389 (3)
C7—C8	1.390 (3)	C7A—C8A	1.383 (3)
C7—O11	1.358 (2)	C7A—O11A	1.365 (3)
C8—C9	1.399 (3)	C8A—C9A	1.396 (3)
C8—O13	1.379 (2)	C8A—O13A	1.383 (3)
C9—C10	1.386 (3)	C9A—C10A	1.386 (3)
C9—O15	1.360 (2)	C9A—O15A	1.361 (3)
C10—H10	0.9500	C10A—H10A	0.9500
C12—H12A	0.9800	C12A—H12D	0.9800
C12—H12B	0.9800	C12A—H12E	0.9800
C12—H12C	0.9800	C12A—H12F	0.9800
C12—O11	1.429 (3)	C12A—O11A	1.422 (3)
C14—H14A	0.9800	C14A—H14D	0.9800
C14—H14B	0.9800	C14A—H14E	0.9800
C14—H14C	0.9800	C14A—H14F	0.9800
C14—O13	1.426 (3)	C14A—O13A	1.421 (3)
C16—H16A	0.9800	C16A—H16D	0.9800
C16—H16B	0.9800	C16A—H16E	0.9800
C16—H16C	0.9800	C16A—H16F	0.9800
C16—O15	1.428 (3)	C16A—O15A	1.422 (3)
C18—C19	1.394 (3)	C18A—C19A	1.392 (3)
C18—C23	1.382 (3)	C18A—C23A	1.385 (3)
C19—H19	0.9500	C19A—H19A	0.9500
C19—C20	1.376 (3)	C19A—C20A	1.373 (3)
C20—H20	0.9500	C20A—H20A	0.9500
C20—C21	1.388 (3)	C20A—C21A	1.386 (3)
C21—C22	1.380 (3)	C21A—C22A	1.383 (3)
C21—O24	1.371 (3)	C21A—O24A	1.362 (3)
C22—H22	0.9500	C22A—H22A	0.9500
C22—C23	1.393 (3)	C22A—C23A	1.384 (3)
C23—H23	0.9500	C23A—H23A	0.9500
C25—H25A	0.9800	C25A—H25D	0.9800
C25—H25B	0.9800	C25A—H25E	0.9800
C25—H25C	0.9800	C25A—H25F	0.9800
C25—O24	1.433 (3)	C25A—O24A	1.425 (3)
C26—C30	1.337 (3)	C26A—C30A	1.336 (3)
C26—O27	1.373 (2)	C26A—O27A	1.367 (3)
C28—H28	0.9500	C28A—H28A	0.9500
C28—C29	1.331 (3)	C28A—C29A	1.330 (4)
C28—O27	1.364 (3)	C28A—O27A	1.365 (3)
C29—H29	0.9500	C29A—H29A	0.9500
C29—C30	1.429 (3)	C29A—C30A	1.428 (3)
C30—H30	0.9500	C30A—H30A	0.9500

N1—C2—C3	92.16 (16)	N1A—C2A—C3A	92.05 (16)
O17—C2—C3	136.14 (19)	O17A—C2A—C3A	135.6 (2)
O17—C2—N1	131.70 (19)	O17A—C2A—N1A	132.3 (2)
C2—C3—H3	111.2	C2A—C3A—H3A	111.0
C2—C3—C4	85.67 (15)	C2A—C3A—C4A	85.79 (15)
C4—C3—H3	111.2	C4A—C3A—H3A	111.0
C26—C3—C2	117.24 (17)	C26A—C3A—C2A	118.24 (18)
C26—C3—H3	111.2	C26A—C3A—H3A	111.0
C26—C3—C4	118.06 (17)	C26A—C3A—C4A	117.50 (18)
C3—C4—H4	111.6	C3A—C4A—H4A	110.9
C18—C4—C3	118.46 (17)	C18A—C4A—C3A	119.68 (18)
C18—C4—H4	111.6	C18A—C4A—H4A	110.9
N1—C4—C3	86.31 (14)	N1A—C4A—C3A	86.26 (15)
N1—C4—H4	111.6	N1A—C4A—H4A	110.9
N1—C4—C18	115.00 (17)	N1A—C4A—C18A	116.01 (17)
C6—C5—C10	122.39 (19)	C6A—C5A—C10A	121.7 (2)
C6—C5—N1	117.93 (18)	C6A—C5A—N1A	118.44 (18)
C10—C5—N1	119.68 (19)	C10A—C5A—N1A	119.8 (2)
C5—C6—H6	120.6	C5A—C6A—H6A	120.4
C5—C6—C7	118.77 (19)	C5A—C6A—C7A	119.2 (2)
C7—C6—H6	120.6	C7A—C6A—H6A	120.4
C6—C7—C8	120.36 (19)	C8A—C7A—C6A	120.3 (2)
O11—C7—C6	123.42 (19)	O11A—C7A—C6A	123.8 (2)
O11—C7—C8	116.21 (18)	O11A—C7A—C8A	115.8 (2)
C7—C8—C9	119.36 (18)	C7A—C8A—C9A	119.6 (2)
O13—C8—C7	120.31 (19)	O13A—C8A—C7A	119.4 (2)
O13—C8—C9	120.29 (18)	O13A—C8A—C9A	120.7 (2)
C10—C9—C8	121.06 (19)	C10A—C9A—C8A	120.7 (2)
O15—C9—C8	115.18 (18)	O15A—C9A—C8A	115.5 (2)
O15—C9—C10	123.8 (2)	O15A—C9A—C10A	123.8 (2)
C5—C10—H10	121.0	C5A—C10A—H10A	120.8
C9—C10—C5	117.9 (2)	C9A—C10A—C5A	118.4 (2)
C9—C10—H10	121.0	C9A—C10A—H10A	120.8
H12A—C12—H12B	109.5	H12D—C12A—H12E	109.5
H12A—C12—H12C	109.5	H12D—C12A—H12F	109.5
H12B—C12—H12C	109.5	H12E—C12A—H12F	109.5
O11—C12—H12A	109.5	O11A—C12A—H12D	109.5
O11—C12—H12B	109.5	O11A—C12A—H12E	109.5
O11—C12—H12C	109.5	O11A—C12A—H12F	109.5
H14A—C14—H14B	109.5	H14D—C14A—H14E	109.5
H14A—C14—H14C	109.5	H14D—C14A—H14F	109.5
H14B—C14—H14C	109.5	H14E—C14A—H14F	109.5
O13—C14—H14A	109.5	O13A—C14A—H14D	109.5
O13—C14—H14B	109.5	O13A—C14A—H14E	109.5
O13—C14—H14C	109.5	O13A—C14A—H14F	109.5
H16A—C16—H16B	109.5	H16D—C16A—H16E	109.5
H16A—C16—H16C	109.5	H16D—C16A—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16A—H16F	109.5
O15—C16—H16A	109.5	O15A—C16A—H16D	109.5
O15—C16—H16B	109.5	O15A—C16A—H16E	109.5
O15—C16—H16C	109.5	O15A—C16A—H16F	109.5
C19—C18—C4	120.71 (18)	C19A—C18A—C4A	121.42 (19)
C23—C18—C4	121.15 (19)	C23A—C18A—C4A	120.67 (19)
C23—C18—C19	118.1 (2)	C23A—C18A—C19A	117.9 (2)
C18—C19—H19	119.4	C18A—C19A—H19A	119.3
C20—C19—C18	121.22 (19)	C20A—C19A—C18A	121.3 (2)
C20—C19—H19	119.4	C20A—C19A—H19A	119.3
C19—C20—H20	120.1	C19A—C20A—H20A	120.0
C19—C20—C21	119.8 (2)	C19A—C20A—C21A	120.0 (2)
C21—C20—H20	120.1	C21A—C20A—H20A	120.0
C22—C21—C20	120.1 (2)	C22A—C21A—C20A	119.8 (2)
O24—C21—C20	115.69 (19)	O24A—C21A—C20A	115.8 (2)
O24—C21—C22	124.15 (19)	O24A—C21A—C22A	124.3 (2)
C21—C22—H22	120.4	C21A—C22A—H22A	120.3
C21—C22—C23	119.3 (2)	C21A—C22A—C23A	119.4 (2)
C23—C22—H22	120.4	C23A—C22A—H22A	120.3
C18—C23—C22	121.4 (2)	C18A—C23A—H23A	119.2
C18—C23—H23	119.3	C22A—C23A—C18A	121.6 (2)
C22—C23—H23	119.3	C22A—C23A—H23A	119.2
H25A—C25—H25B	109.5	H25D—C25A—H25E	109.5
H25A—C25—H25C	109.5	H25D—C25A—H25F	109.5
H25B—C25—H25C	109.5	H25E—C25A—H25F	109.5
O24—C25—H25A	109.5	O24A—C25A—H25D	109.5
O24—C25—H25B	109.5	O24A—C25A—H25E	109.5
O24—C25—H25C	109.5	O24A—C25A—H25F	109.5
C30—C26—C3	135.1 (2)	C30A—C26A—C3A	136.0 (2)
C30—C26—O27	109.77 (18)	C30A—C26A—O27A	110.0 (2)
O27—C26—C3	115.08 (17)	O27A—C26A—C3A	113.85 (18)
C29—C28—H28	124.7	C29A—C28A—H28A	124.9
C29—C28—O27	110.6 (2)	C29A—C28A—O27A	110.3 (2)
O27—C28—H28	124.7	O27A—C28A—H28A	124.9
C28—C29—H29	126.8	C28A—C29A—H29A	126.7
C28—C29—C30	106.4 (2)	C28A—C29A—C30A	106.7 (2)
C30—C29—H29	126.8	C30A—C29A—H29A	126.7
C26—C30—C29	106.8 (2)	C26A—C30A—C29A	106.5 (2)
C26—C30—H30	126.6	C26A—C30A—H30A	126.8
C29—C30—H30	126.6	C29A—C30A—H30A	126.8
C2—N1—C4	95.79 (15)	C2A—N1A—C4A	95.65 (16)
C2—N1—C5	133.62 (17)	C2A—N1A—C5A	134.43 (18)
C5—N1—C4	130.46 (17)	C5A—N1A—C4A	129.87 (17)
C7—O11—C12	117.12 (16)	C7A—O11A—C12A	117.18 (18)
C8—O13—C14	113.77 (17)	C8A—O13A—C14A	113.03 (18)
C9—O15—C16	116.97 (17)	C9A—O15A—C16A	116.93 (18)
C21—O24—C25	117.15 (18)	C21A—O24A—C25A	118.01 (17)
C28—O27—C26	106.42 (16)	C28A—O27A—C26A	106.54 (18)

C2—C3—C4—C18	−118.34 (18)	C2A—C3A—C4A—C18A	121.34 (19)
C2—C3—C4—N1	−1.80 (14)	C2A—C3A—C4A—N1A	3.40 (15)
C2—C3—C26—C30	137.0 (2)	C2A—C3A—C26A—C30A	5.5 (4)
C2—C3—C26—O27	−43.8 (2)	C2A—C3A—C26A—O27A	180.00 (18)
C3—C2—N1—C4	−2.08 (16)	C3A—C2A—N1A—C4A	3.91 (17)
C3—C2—N1—C5	−178.1 (2)	C3A—C2A—N1A—C5A	−178.4 (2)
C3—C4—C18—C19	55.5 (3)	C3A—C4A—C18A—C19A	−55.5 (3)
C3—C4—C18—C23	−125.2 (2)	C3A—C4A—C18A—C23A	126.0 (2)
C3—C4—N1—C2	2.04 (16)	C3A—C4A—N1A—C2A	−3.82 (17)
C3—C4—N1—C5	178.3 (2)	C3A—C4A—N1A—C5A	178.3 (2)
C3—C26—C30—C29	179.5 (2)	C3A—C26A—C30A—C29A	175.6 (2)
C3—C26—O27—C28	−179.18 (17)	C3A—C26A—O27A—C28A	−176.12 (19)
C4—C3—C26—C30	−122.7 (3)	C4A—C3A—C26A—C30A	−95.2 (3)
C4—C3—C26—O27	56.4 (2)	C4A—C3A—C26A—O27A	79.3 (2)
C4—C18—C19—C20	178.27 (19)	C4A—C18A—C19A—C20A	−178.1 (2)
C4—C18—C23—C22	−179.13 (19)	C4A—C18A—C23A—C22A	178.84 (19)
C5—C6—C7—C8	−0.4 (3)	C5A—C6A—C7A—C8A	−1.1 (3)
C5—C6—C7—O11	−179.94 (18)	C5A—C6A—C7A—O11A	177.4 (2)
C6—C5—C10—C9	−1.1 (3)	C6A—C5A—C10A—C9A	0.3 (3)
C6—C5—N1—C2	170.6 (2)	C6A—C5A—N1A—C2A	−176.6 (2)
C6—C5—N1—C4	−4.3 (3)	C6A—C5A—N1A—C4A	0.4 (3)
C6—C7—C8—C9	−2.8 (3)	C6A—C7A—C8A—C9A	1.7 (3)
C6—C7—C8—O13	174.78 (18)	C6A—C7A—C8A—O13A	176.0 (2)
C6—C7—O11—C12	−1.0 (3)	C6A—C7A—O11A—C12A	−7.1 (3)
C7—C8—C9—C10	4.2 (3)	C7A—C8A—C9A—C10A	−1.3 (3)
C7—C8—C9—O15	−176.39 (18)	C7A—C8A—C9A—O15A	178.0 (2)
C7—C8—O13—C14	95.2 (2)	C7A—C8A—O13A—C14A	96.8 (2)
C8—C7—O11—C12	179.44 (18)	C8A—C7A—O11A—C12A	171.5 (2)
C8—C9—C10—C5	−2.2 (3)	C8A—C9A—C10A—C5A	0.4 (3)
C8—C9—O15—C16	172.20 (19)	C8A—C9A—O15A—C16A	−168.2 (2)
C9—C8—O13—C14	−87.2 (2)	C9A—C8A—O13A—C14A	−89.0 (3)
C10—C5—C6—C7	2.4 (3)	C10A—C5A—C6A—C7A	0.1 (3)
C10—C5—N1—C2	−9.4 (3)	C10A—C5A—N1A—C2A	3.8 (4)
C10—C5—N1—C4	175.72 (19)	C10A—C5A—N1A—C4A	−179.3 (2)
C10—C9—O15—C16	−8.4 (3)	C10A—C9A—O15A—C16A	11.1 (3)
C18—C4—N1—C2	121.84 (18)	C18A—C4A—N1A—C2A	−125.18 (19)
C18—C4—N1—C5	−61.9 (3)	C18A—C4A—N1A—C5A	57.0 (3)
C18—C19—C20—C21	0.8 (3)	C18A—C19A—C20A—C21A	0.0 (4)
C19—C18—C23—C22	0.1 (3)	C19A—C18A—C23A—C22A	0.3 (3)
C19—C20—C21—C22	0.3 (3)	C19A—C20A—C21A—C22A	−1.3 (3)
C19—C20—C21—O24	−178.46 (19)	C19A—C20A—C21A—O24A	177.5 (2)
C20—C21—C22—C23	−1.1 (3)	C20A—C21A—C22A—C23A	2.0 (3)
C20—C21—O24—C25	−167.21 (19)	C20A—C21A—O24A—C25A	171.6 (2)
C21—C22—C23—C18	0.9 (3)	C21A—C22A—C23A—C18A	−1.5 (3)
C22—C21—O24—C25	14.1 (3)	C22A—C21A—O24A—C25A	−9.7 (3)
C23—C18—C19—C20	−1.0 (3)	C23A—C18A—C19A—C20A	0.5 (3)
C26—C3—C4—C18	123.0 (2)	C26A—C3A—C4A—C18A	−118.9 (2)
C26—C3—C4—N1	−120.48 (18)	C26A—C3A—C4A—N1A	123.18 (19)
C28—C29—C30—C26	−0.8 (3)	C28A—C29A—C30A—C26A	−1.4 (3)
C29—C28—O27—C26	−0.7 (2)	C29A—C28A—O27A—C26A	−0.7 (3)
C30—C26—O27—C28	0.2 (2)	C30A—C26A—O27A—C28A	−0.2 (3)
N1—C2—C3—C4	1.96 (15)	N1A—C2A—C3A—C4A	−3.69 (16)
N1—C2—C3—C26	121.41 (19)	N1A—C2A—C3A—C26A	−122.8 (2)
N1—C4—C18—C19	−44.4 (3)	N1A—C4A—C18A—C19A	45.7 (3)
N1—C4—C18—C23	134.9 (2)	N1A—C4A—C18A—C23A	−132.8 (2)
N1—C5—C6—C7	−177.62 (18)	N1A—C5A—C6A—C7A	−179.48 (19)
N1—C5—C10—C9	178.89 (18)	N1A—C5A—C10A—C9A	179.85 (19)
O11—C7—C8—C9	176.79 (18)	O11A—C7A—C8A—C9A	−176.9 (2)
O11—C7—C8—O13	−5.6 (3)	O11A—C7A—C8A—O13A	−2.7 (3)
O13—C8—C9—C10	−173.46 (19)	O13A—C8A—C9A—C10A	−175.5 (2)
O13—C8—C9—O15	6.0 (3)	O13A—C8A—C9A—O15A	3.8 (3)
O15—C9—C10—C5	178.39 (19)	O15A—C9A—C10A—C5A	−178.9 (2)
O17—C2—C3—C4	−177.5 (3)	O17A—C2A—C3A—C4A	176.5 (3)
O17—C2—C3—C26	−58.0 (3)	O17A—C2A—C3A—C26A	57.4 (3)
O17—C2—N1—C4	177.4 (2)	O17A—C2A—N1A—C4A	−176.3 (2)
O17—C2—N1—C5	1.3 (4)	O17A—C2A—N1A—C5A	1.4 (4)
O24—C21—C22—C23	177.50 (19)	O24A—C21A—C22A—C23A	−176.6 (2)
O27—C26—C30—C29	0.4 (2)	O27A—C26A—C30A—C29A	1.0 (3)
O27—C28—C29—C30	0.9 (3)	O27A—C28A—C29A—C30A	1.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O17	0.95	2.50	3.103 (3)	122
C12—H12C···O11ⁱ	0.98	2.48	3.171 (3)	127
C12—H12C···O13ⁱ	0.98	2.55	3.482 (3)	159
C22—H22···O24Aⁱⁱ	0.95	2.39	3.143 (3)	136
C10A—H10A···O17A	0.95	2.53	3.144 (3)	123
C22A—H22A···O24ⁱⁱⁱ	0.95	2.40	3.274 (3)	153

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y−1, z; (iii) x−1, y, z.

4-(4-Methoxyphenyl)-3-(naphthalen-1-yl)-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (3) top

Crystal data top

C₂₉H₂₇NO₅	Z = 2
M_r = 469.51	F(000) = 496
Triclinic, P1	D_x = 1.330 Mg m⁻³
a = 10.4633 (6) Å	Cu Kα radiation, λ = 1.54178 Å
b = 11.3180 (6) Å	Cell parameters from 6199 reflections
c = 11.6008 (6) Å	θ = 4.1–69.6°
α = 104.628 (3)°	µ = 0.74 mm⁻¹
β = 99.056 (4)°	T = 100 K
γ = 112.929 (3)°	Parallelepiped, clear colourless
V = 1172.74 (12) Å³	0.27 × 0.15 × 0.04 mm

Data collection top

Bruker APEXII Kappa Duo diffractometer	4385 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	3453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
Detector resolution: 8.33 pixels mm^-1	θ_max = 70.1°, θ_min = 4.1°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −13→13
T_min = 0.598, T_max = 0.753	l = −13→14
18268 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.188	w = 1/[σ²(F_o²) + (0.1228P)² + 0.0444P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
4385 reflections	Δρ_max = 0.32 e Å⁻³
320 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O11	0.27184 (19)	0.98480 (17)	0.56161 (14)	0.0318 (4)
O13	0.28619 (18)	1.19859 (16)	0.49316 (14)	0.0318 (4)
O15	0.33384 (18)	1.21545 (16)	0.27846 (14)	0.0310 (4)
O17	0.50893 (19)	0.88524 (17)	0.04762 (15)	0.0335 (4)
O24	−0.05470 (18)	0.24692 (16)	0.19767 (15)	0.0330 (4)
N1	0.4283 (2)	0.81934 (18)	0.20997 (16)	0.0252 (4)
C2	0.4908 (2)	0.8174 (2)	0.1145 (2)	0.0262 (5)
C3	0.5262 (2)	0.7014 (2)	0.13022 (19)	0.0260 (5)
H3	0.465982	0.614244	0.058406	0.031*
C4	0.4548 (2)	0.7094 (2)	0.2403 (2)	0.0265 (5)
H4	0.527251	0.744487	0.323123	0.032*
C5	0.3828 (2)	0.9105 (2)	0.27668 (19)	0.0246 (4)
C6	0.3466 (2)	0.8950 (2)	0.38390 (19)	0.0257 (4)
H6	0.346697	0.821091	0.408594	0.031*
C7	0.3102 (2)	0.9898 (2)	0.45462 (19)	0.0266 (5)
C8	0.3106 (2)	1.0983 (2)	0.41895 (19)	0.0275 (5)
C9	0.3416 (2)	1.1088 (2)	0.3075 (2)	0.0257 (4)
C10	0.3777 (2)	1.0147 (2)	0.23476 (19)	0.0266 (5)
H10	0.398219	1.021108	0.159038	0.032*
C12	0.2438 (3)	0.8634 (2)	0.5902 (2)	0.0333 (5)
H12A	0.171099	0.783988	0.519281	0.050*
H12B	0.207551	0.868452	0.663356	0.050*
H12C	0.333556	0.854173	0.607777	0.050*
C14	0.1374 (3)	1.1670 (3)	0.4731 (3)	0.0387 (6)
H14A	0.092431	1.143801	0.384612	0.058*
H14B	0.128477	1.246329	0.521876	0.058*
H14C	0.088702	1.089081	0.499073	0.058*
C16	0.3114 (3)	1.2035 (2)	0.1502 (2)	0.0307 (5)
H16A	0.227553	1.116488	0.099011	0.046*
H16B	0.397713	1.206794	0.125353	0.046*
H16C	0.293765	1.279194	0.138445	0.046*
C18	0.3190 (2)	0.5863 (2)	0.22621 (19)	0.0257 (5)
C19	0.2062 (2)	0.5191 (2)	0.11641 (19)	0.0267 (5)
H19	0.215837	0.551660	0.048795	0.032*
C20	0.0801 (2)	0.4060 (2)	0.1029 (2)	0.0274 (5)
H20	0.004458	0.361916	0.026919	0.033*
C21	0.0648 (2)	0.3571 (2)	0.2016 (2)	0.0280 (5)
C22	0.1773 (3)	0.4226 (2)	0.3123 (2)	0.0299 (5)
H22	0.167774	0.389856	0.379824	0.036*
C23	0.3029 (3)	0.5352 (2)	0.3241 (2)	0.0290 (5)
H23	0.379153	0.578520	0.399561	0.035*
C25	−0.1770 (3)	0.1897 (2)	0.0908 (2)	0.0376 (5)
H25A	−0.152589	0.151104	0.016782	0.056*
H25B	−0.203443	0.261295	0.080580	0.056*
H25C	−0.258858	0.117424	0.101861	0.056*
C26	0.6851 (2)	0.7344 (2)	0.16019 (19)	0.0280 (5)
C27	0.7848 (3)	0.8487 (2)	0.1473 (2)	0.0310 (5)
H27	0.753751	0.909115	0.122201	0.037*
C28	0.9327 (3)	0.8786 (3)	0.1706 (2)	0.0348 (5)
H28	0.999336	0.957458	0.159343	0.042*
C29	0.9801 (3)	0.7948 (3)	0.2092 (2)	0.0335 (5)
H29	1.079396	0.814681	0.223379	0.040*
C30	0.8821 (3)	0.6781 (2)	0.2281 (2)	0.0313 (5)
C31	0.9306 (3)	0.5940 (3)	0.2752 (2)	0.0359 (6)
H31	1.029853	0.613391	0.290242	0.043*
C32	0.8369 (3)	0.4857 (3)	0.2994 (2)	0.0408 (6)
H32	0.871431	0.431380	0.332242	0.049*
C33	0.6895 (3)	0.4547 (3)	0.2755 (3)	0.0392 (6)
H33	0.624951	0.379803	0.293207	0.047*
C34	0.6376 (3)	0.5316 (2)	0.2268 (2)	0.0347 (5)
H34	0.537114	0.507401	0.208794	0.042*
C35	0.7323 (2)	0.6464 (2)	0.2033 (2)	0.0289 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O11	0.0418 (9)	0.0346 (9)	0.0217 (7)	0.0216 (7)	0.0101 (7)	0.0060 (6)
O13	0.0374 (9)	0.0288 (8)	0.0259 (8)	0.0197 (7)	0.0064 (6)	−0.0019 (6)
O15	0.0426 (9)	0.0261 (8)	0.0262 (8)	0.0201 (7)	0.0106 (7)	0.0041 (6)
O17	0.0398 (9)	0.0336 (9)	0.0345 (9)	0.0219 (7)	0.0173 (7)	0.0109 (7)
O24	0.0339 (9)	0.0256 (8)	0.0346 (8)	0.0113 (7)	0.0078 (7)	0.0074 (6)
N1	0.0282 (9)	0.0220 (9)	0.0256 (9)	0.0142 (7)	0.0088 (7)	0.0032 (7)
C2	0.0267 (11)	0.0246 (10)	0.0249 (10)	0.0126 (9)	0.0066 (8)	0.0034 (8)
C3	0.0280 (11)	0.0211 (10)	0.0233 (10)	0.0114 (8)	0.0053 (8)	−0.0008 (8)
C4	0.0286 (11)	0.0241 (10)	0.0251 (10)	0.0144 (9)	0.0068 (8)	0.0020 (8)
C5	0.0204 (10)	0.0216 (10)	0.0238 (10)	0.0089 (8)	0.0017 (8)	−0.0014 (8)
C6	0.0234 (10)	0.0242 (10)	0.0237 (10)	0.0102 (8)	0.0026 (8)	0.0021 (8)
C7	0.0264 (11)	0.0290 (11)	0.0197 (9)	0.0136 (9)	0.0036 (8)	0.0011 (8)
C8	0.0278 (11)	0.0275 (11)	0.0210 (10)	0.0140 (9)	0.0033 (8)	−0.0019 (8)
C9	0.0248 (10)	0.0214 (10)	0.0250 (10)	0.0106 (8)	0.0032 (8)	0.0006 (8)
C10	0.0273 (11)	0.0250 (10)	0.0240 (10)	0.0120 (9)	0.0073 (8)	0.0022 (8)
C12	0.0383 (13)	0.0344 (12)	0.0249 (10)	0.0159 (10)	0.0095 (9)	0.0067 (9)
C14	0.0397 (14)	0.0311 (12)	0.0471 (14)	0.0199 (11)	0.0189 (11)	0.0058 (10)
C16	0.0369 (12)	0.0272 (11)	0.0284 (11)	0.0169 (10)	0.0098 (9)	0.0060 (9)
C18	0.0282 (11)	0.0208 (10)	0.0259 (10)	0.0140 (9)	0.0066 (8)	0.0006 (8)
C19	0.0313 (11)	0.0254 (10)	0.0236 (10)	0.0153 (9)	0.0081 (8)	0.0044 (8)
C20	0.0288 (11)	0.0235 (10)	0.0246 (10)	0.0124 (9)	0.0040 (8)	0.0009 (8)
C21	0.0295 (11)	0.0218 (10)	0.0317 (11)	0.0135 (9)	0.0103 (9)	0.0038 (8)
C22	0.0349 (12)	0.0263 (11)	0.0293 (11)	0.0160 (9)	0.0083 (9)	0.0077 (8)
C23	0.0326 (12)	0.0275 (11)	0.0246 (10)	0.0154 (9)	0.0044 (9)	0.0046 (8)
C25	0.0340 (13)	0.0284 (12)	0.0369 (12)	0.0060 (10)	0.0058 (10)	0.0057 (10)
C26	0.0294 (12)	0.0272 (11)	0.0210 (9)	0.0142 (9)	0.0049 (8)	−0.0028 (8)
C27	0.0318 (12)	0.0323 (11)	0.0241 (10)	0.0147 (9)	0.0073 (9)	0.0019 (9)
C28	0.0292 (12)	0.0356 (12)	0.0284 (11)	0.0103 (10)	0.0063 (9)	0.0015 (9)
C29	0.0247 (11)	0.0399 (13)	0.0253 (10)	0.0129 (10)	0.0047 (8)	−0.0014 (9)
C30	0.0303 (12)	0.0319 (11)	0.0230 (10)	0.0167 (10)	0.0037 (8)	−0.0061 (8)
C31	0.0339 (13)	0.0354 (12)	0.0333 (12)	0.0223 (11)	0.0040 (10)	−0.0033 (10)
C32	0.0439 (15)	0.0338 (13)	0.0422 (14)	0.0250 (12)	0.0047 (11)	0.0018 (10)
C33	0.0391 (14)	0.0284 (12)	0.0480 (14)	0.0186 (10)	0.0091 (11)	0.0067 (10)
C34	0.0292 (12)	0.0286 (11)	0.0390 (12)	0.0138 (10)	0.0070 (10)	0.0009 (9)
C35	0.0278 (11)	0.0259 (10)	0.0241 (10)	0.0128 (9)	0.0036 (8)	−0.0045 (8)

Geometric parameters (Å, º) top

O11—C7	1.371 (3)	C16—H16B	0.9800
O11—C12	1.426 (3)	C16—H16C	0.9800
O13—C8	1.377 (2)	C18—C19	1.390 (3)
O13—C14	1.420 (3)	C18—C23	1.402 (3)
O15—C9	1.360 (3)	C19—H19	0.9500
O15—C16	1.432 (3)	C19—C20	1.387 (3)
O17—C2	1.209 (3)	C20—H20	0.9500
O24—C21	1.363 (3)	C20—C21	1.397 (3)
O24—C25	1.429 (3)	C21—C22	1.396 (3)
N1—C2	1.372 (3)	C22—H22	0.9500
N1—C4	1.486 (3)	C22—C23	1.386 (3)
N1—C5	1.409 (3)	C23—H23	0.9500
C2—C3	1.540 (3)	C25—H25A	0.9800
C3—H3	1.0000	C25—H25B	0.9800
C3—C4	1.578 (3)	C25—H25C	0.9800
C3—C26	1.514 (3)	C26—C27	1.370 (3)
C4—H4	1.0000	C26—C35	1.429 (3)
C4—C18	1.502 (3)	C27—H27	0.9500
C5—C6	1.388 (3)	C27—C28	1.413 (3)
C5—C10	1.400 (3)	C28—H28	0.9500
C6—H6	0.9500	C28—C29	1.363 (4)
C6—C7	1.394 (3)	C29—H29	0.9500
C7—C8	1.390 (3)	C29—C30	1.416 (4)
C8—C9	1.404 (3)	C30—C31	1.420 (3)
C9—C10	1.396 (3)	C30—C35	1.427 (3)
C10—H10	0.9500	C31—H31	0.9500
C12—H12A	0.9800	C31—C32	1.366 (4)
C12—H12B	0.9800	C32—H32	0.9500
C12—H12C	0.9800	C32—C33	1.405 (4)
C14—H14A	0.9800	C33—H33	0.9500
C14—H14B	0.9800	C33—C34	1.375 (4)
C14—H14C	0.9800	C34—H34	0.9500
C16—H16A	0.9800	C34—C35	1.416 (3)

C7—O11—C12	117.44 (17)	H16A—C16—H16C	109.5
C8—O13—C14	113.86 (17)	H16B—C16—H16C	109.5
C9—O15—C16	116.64 (16)	C19—C18—C4	121.4 (2)
C21—O24—C25	116.74 (18)	C19—C18—C23	118.0 (2)
C2—N1—C4	95.51 (16)	C23—C18—C4	120.6 (2)
C2—N1—C5	133.37 (19)	C18—C19—H19	119.1
C5—N1—C4	129.86 (18)	C20—C19—C18	121.8 (2)
O17—C2—N1	131.4 (2)	C20—C19—H19	119.1
O17—C2—C3	136.3 (2)	C19—C20—H20	120.2
N1—C2—C3	92.34 (17)	C19—C20—C21	119.6 (2)
C2—C3—H3	111.6	C21—C20—H20	120.2
C2—C3—C4	85.48 (16)	O24—C21—C20	124.1 (2)
C4—C3—H3	111.6	O24—C21—C22	116.5 (2)
C26—C3—C2	115.81 (18)	C22—C21—C20	119.4 (2)
C26—C3—H3	111.6	C21—C22—H22	119.9
C26—C3—C4	118.38 (17)	C23—C22—C21	120.2 (2)
N1—C4—C3	86.66 (16)	C23—C22—H22	119.9
N1—C4—H4	112.2	C18—C23—H23	119.5
N1—C4—C18	113.86 (18)	C22—C23—C18	121.0 (2)
C3—C4—H4	112.2	C22—C23—H23	119.5
C18—C4—C3	117.43 (17)	O24—C25—H25A	109.5
C18—C4—H4	112.2	O24—C25—H25B	109.5
C6—C5—N1	118.38 (19)	O24—C25—H25C	109.5
C6—C5—C10	122.10 (19)	H25A—C25—H25B	109.5
C10—C5—N1	119.51 (19)	H25A—C25—H25C	109.5
C5—C6—H6	120.6	H25B—C25—H25C	109.5
C5—C6—C7	118.7 (2)	C27—C26—C3	120.7 (2)
C7—C6—H6	120.6	C27—C26—C35	119.4 (2)
O11—C7—C6	124.1 (2)	C35—C26—C3	119.9 (2)
O11—C7—C8	115.20 (19)	C26—C27—H27	119.3
C8—C7—C6	120.7 (2)	C26—C27—C28	121.5 (2)
O13—C8—C7	121.2 (2)	C28—C27—H27	119.3
O13—C8—C9	119.2 (2)	C27—C28—H28	119.9
C7—C8—C9	119.57 (19)	C29—C28—C27	120.2 (2)
O15—C9—C8	115.04 (18)	C29—C28—H28	119.9
O15—C9—C10	124.3 (2)	C28—C29—H29	119.8
C10—C9—C8	120.7 (2)	C28—C29—C30	120.4 (2)
C5—C10—H10	121.0	C30—C29—H29	119.8
C9—C10—C5	118.1 (2)	C29—C30—C31	121.3 (2)
C9—C10—H10	121.0	C29—C30—C35	119.7 (2)
O11—C12—H12A	109.5	C31—C30—C35	119.1 (2)
O11—C12—H12B	109.5	C30—C31—H31	119.5
O11—C12—H12C	109.5	C32—C31—C30	121.0 (2)
H12A—C12—H12B	109.5	C32—C31—H31	119.5
H12A—C12—H12C	109.5	C31—C32—H32	120.0
H12B—C12—H12C	109.5	C31—C32—C33	120.0 (2)
O13—C14—H14A	109.5	C33—C32—H32	120.0
O13—C14—H14B	109.5	C32—C33—H33	119.6
O13—C14—H14C	109.5	C34—C33—C32	120.7 (3)
H14A—C14—H14B	109.5	C34—C33—H33	119.6
H14A—C14—H14C	109.5	C33—C34—H34	119.6
H14B—C14—H14C	109.5	C33—C34—C35	120.8 (2)
O15—C16—H16A	109.5	C35—C34—H34	119.6
O15—C16—H16B	109.5	C30—C35—C26	118.7 (2)
O15—C16—H16C	109.5	C34—C35—C26	122.8 (2)
H16A—C16—H16B	109.5	C34—C35—C30	118.4 (2)

O11—C7—C8—O13	5.3 (3)	C6—C7—C8—O13	−174.7 (2)
O11—C7—C8—C9	−176.97 (19)	C6—C7—C8—C9	2.9 (3)
O13—C8—C9—O15	−4.7 (3)	C7—C8—C9—O15	177.54 (19)
O13—C8—C9—C10	175.13 (19)	C7—C8—C9—C10	−2.6 (3)
O15—C9—C10—C5	179.47 (19)	C8—C9—C10—C5	−0.4 (3)
O17—C2—C3—C4	178.8 (3)	C10—C5—C6—C7	−2.8 (3)
O17—C2—C3—C26	59.3 (3)	C12—O11—C7—C6	−11.1 (3)
O24—C21—C22—C23	179.86 (19)	C12—O11—C7—C8	168.8 (2)
N1—C2—C3—C4	−0.65 (16)	C14—O13—C8—C7	−86.9 (3)
N1—C2—C3—C26	−120.09 (18)	C14—O13—C8—C9	95.4 (2)
N1—C4—C18—C19	53.2 (3)	C16—O15—C9—C8	−157.75 (19)
N1—C4—C18—C23	−127.1 (2)	C16—O15—C9—C10	22.4 (3)
N1—C5—C6—C7	176.06 (19)	C18—C19—C20—C21	−0.1 (3)
N1—C5—C10—C9	−175.73 (19)	C19—C18—C23—C22	−1.0 (3)
C2—N1—C4—C3	−0.68 (17)	C19—C20—C21—O24	179.90 (18)
C2—N1—C4—C18	−119.28 (19)	C19—C20—C21—C22	−0.3 (3)
C2—N1—C5—C6	−168.6 (2)	C20—C21—C22—C23	0.1 (3)
C2—N1—C5—C10	10.3 (4)	C21—C22—C23—C18	0.6 (3)
C2—C3—C4—N1	0.60 (15)	C23—C18—C19—C20	0.8 (3)
C2—C3—C4—C18	115.8 (2)	C25—O24—C21—C20	−7.7 (3)
C2—C3—C26—C27	−13.3 (3)	C25—O24—C21—C22	172.53 (19)
C2—C3—C26—C35	166.16 (18)	C26—C3—C4—N1	117.59 (19)
C3—C4—C18—C19	−45.9 (3)	C26—C3—C4—C18	−127.2 (2)
C3—C4—C18—C23	133.8 (2)	C26—C27—C28—C29	−1.3 (3)
C3—C26—C27—C28	−177.73 (19)	C27—C26—C35—C30	−1.9 (3)
C3—C26—C35—C30	178.56 (17)	C27—C26—C35—C34	175.7 (2)
C3—C26—C35—C34	−3.8 (3)	C27—C28—C29—C30	−1.0 (3)
C4—N1—C2—O17	−178.8 (2)	C28—C29—C30—C31	−176.2 (2)
C4—N1—C2—C3	0.70 (17)	C28—C29—C30—C35	1.7 (3)
C4—N1—C5—C6	−4.7 (3)	C29—C30—C31—C32	176.6 (2)
C4—N1—C5—C10	174.2 (2)	C29—C30—C35—C26	−0.3 (3)
C4—C3—C26—C27	−112.6 (2)	C29—C30—C35—C34	−178.04 (19)
C4—C3—C26—C35	66.8 (2)	C30—C31—C32—C33	1.1 (4)
C4—C18—C19—C20	−179.57 (18)	C31—C30—C35—C26	177.73 (19)
C4—C18—C23—C22	179.31 (19)	C31—C30—C35—C34	0.0 (3)
C5—N1—C2—O17	−11.1 (4)	C31—C32—C33—C34	0.6 (4)
C5—N1—C2—C3	168.4 (2)	C32—C33—C34—C35	−2.0 (4)
C5—N1—C4—C3	−169.0 (2)	C33—C34—C35—C26	−176.0 (2)
C5—N1—C4—C18	72.4 (3)	C33—C34—C35—C30	1.7 (3)
C5—C6—C7—O11	179.61 (19)	C35—C26—C27—C28	2.8 (3)
C5—C6—C7—C8	−0.3 (3)	C35—C30—C31—C32	−1.4 (3)
C6—C5—C10—C9	3.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O13ⁱ	1.00	2.41	3.396 (3)	171
C10—H10···O17	0.95	2.50	3.105 (3)	122
C16—H16B···O17ⁱⁱ	0.98	2.53	3.387 (3)	146
C27—H27···O17	0.95	2.46	3.156 (3)	131

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+2, −z.

3-(3,4-Dimethoxyphenyl)-4-(4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (4) top

Crystal data top

C₂₇H₂₉NO₇	F(000) = 1016
M_r = 479.51	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.858 (2) Å	Cell parameters from 1212 reflections
b = 22.769 (5) Å	θ = 2.6–23.1°
c = 12.822 (2) Å	µ = 0.10 mm⁻¹
β = 109.839 (6)°	T = 100 K
V = 2432.4 (9) Å³	Block, clear colourless
Z = 4	0.41 × 0.24 × 0.12 mm

Data collection top

Bruker D8 Quest ECO diffractometer	5620 independent reflections
Radiation source: standard sealed X-ray tube, Siemens, KFF Mo 2K -90 C	4062 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
Detector resolution: 5.12 pixels mm^-1	θ_max = 27.6°, θ_min = 3.0°
ω and φ scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −29→29
T_min = 0.701, T_max = 0.746	l = −16→16
27592 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.041P)² + 1.0883P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5620 reflections	Δρ_max = 0.29 e Å⁻³
322 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C2	0.84113 (18)	0.49962 (7)	0.37411 (13)	0.0162 (3)
C3	0.87377 (18)	0.51826 (7)	0.26892 (12)	0.0157 (3)
H3	0.990712	0.526648	0.287047	0.019*
C4	0.78269 (18)	0.57636 (7)	0.27621 (12)	0.0148 (3)
H4	0.674264	0.577567	0.217418	0.018*
C5	0.71160 (18)	0.57666 (7)	0.45968 (12)	0.0159 (3)
C6	0.65806 (18)	0.63452 (7)	0.44685 (13)	0.0172 (3)
H6	0.662260	0.657388	0.385923	0.021*
C7	0.59827 (18)	0.65825 (7)	0.52487 (13)	0.0180 (3)
C8	0.59158 (19)	0.62472 (7)	0.61437 (13)	0.0191 (3)
C9	0.63928 (19)	0.56597 (7)	0.62198 (13)	0.0184 (3)
C10	0.70149 (18)	0.54172 (7)	0.54604 (13)	0.0172 (3)
H10	0.736532	0.50	0.552834	0.021*
C12	0.5546 (2)	0.75159 (7)	0.43424 (15)	0.0287 (4)
H12A	0.666405	0.754183	0.437184	0.043*
H12B	0.515127	0.790932	0.442413	0.043*
H12C	0.488671	0.734895	0.362860	0.043*
C14	0.3821 (2)	0.66089 (8)	0.67118 (15)	0.0280 (4)
H14A	0.320459	0.625990	0.636791	0.042*
H14B	0.351633	0.693908	0.619170	0.042*
H14C	0.359175	0.670784	0.738701	0.042*
C16	0.65212 (19)	0.47368 (7)	0.71345 (14)	0.0206 (3)
H16A	0.621470	0.456024	0.773065	0.031*
H16B	0.766690	0.466983	0.727773	0.031*
H16C	0.589438	0.455723	0.642492	0.031*
C18	0.86952 (18)	0.63357 (7)	0.28249 (12)	0.0156 (3)
C19	1.02182 (19)	0.64340 (7)	0.36055 (13)	0.0180 (3)
H19	1.072542	0.613428	0.412061	0.022*
C20	1.09906 (19)	0.69640 (7)	0.36331 (13)	0.0196 (3)
H20	1.202840	0.702656	0.416259	0.024*
C21	1.02479 (19)	0.74069 (7)	0.28846 (13)	0.0186 (3)
C22	0.8729 (2)	0.73193 (7)	0.21209 (14)	0.0212 (3)
H22	0.821209	0.762239	0.161711	0.025*
C23	0.79668 (19)	0.67835 (7)	0.20982 (13)	0.0186 (3)
H23	0.692445	0.672332	0.157316	0.022*
C25	1.0344 (2)	0.83756 (7)	0.22111 (17)	0.0295 (4)
H25A	0.933370	0.848261	0.231571	0.044*
H25B	1.012457	0.824058	0.144805	0.044*
H25C	1.105287	0.871891	0.235303	0.044*
C26	0.81566 (18)	0.47948 (7)	0.16849 (12)	0.0160 (3)
C27	0.65677 (18)	0.45884 (7)	0.13051 (12)	0.0155 (3)
H27	0.584360	0.470964	0.166563	0.019*
C28	0.60498 (18)	0.42096 (7)	0.04097 (13)	0.0162 (3)
C29	0.7138 (2)	0.40170 (7)	−0.01069 (13)	0.0186 (3)
C30	0.8684 (2)	0.42271 (7)	0.02550 (14)	0.0211 (3)
H30	0.941328	0.410543	−0.010129	0.025*
C31	0.91876 (19)	0.46188 (7)	0.11445 (13)	0.0197 (3)
H31	1.025421	0.476615	0.138081	0.024*
C33	0.33850 (19)	0.41571 (7)	0.04667 (14)	0.0211 (3)
H33A	0.374581	0.402140	0.123772	0.032*
H33B	0.234442	0.397885	0.005896	0.032*
H33C	0.327728	0.458564	0.044877	0.032*
C35	0.7669 (2)	0.33184 (8)	−0.13163 (16)	0.0336 (4)
H35A	0.847282	0.313216	−0.067872	0.050*
H35B	0.819835	0.359731	−0.166161	0.050*
H35C	0.711845	0.301696	−0.185730	0.050*
N1	0.77324 (15)	0.55260 (5)	0.38186 (10)	0.0153 (3)
O11	0.54523 (14)	0.71481 (5)	0.52208 (9)	0.0219 (3)
O13	0.54909 (14)	0.64926 (5)	0.69862 (9)	0.0237 (3)
O15	0.62117 (15)	0.53530 (5)	0.70912 (10)	0.0250 (3)
O17	0.86311 (14)	0.45559 (5)	0.43039 (9)	0.0210 (3)
O24	1.11080 (14)	0.79146 (5)	0.29664 (10)	0.0247 (3)
O32	0.45374 (13)	0.39892 (5)	−0.00387 (9)	0.0193 (2)
O34	0.65265 (14)	0.36228 (5)	−0.09539 (10)	0.0243 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0141 (7)	0.0173 (8)	0.0137 (7)	−0.0023 (6)	0.0002 (6)	−0.0024 (6)
C3	0.0149 (7)	0.0166 (7)	0.0137 (7)	0.0005 (6)	0.0022 (6)	−0.0003 (6)
C4	0.0162 (7)	0.0161 (7)	0.0117 (7)	−0.0016 (6)	0.0042 (6)	0.0010 (6)
C5	0.0134 (7)	0.0186 (7)	0.0141 (7)	−0.0030 (6)	0.0025 (6)	−0.0016 (6)
C6	0.0179 (7)	0.0174 (7)	0.0155 (7)	−0.0026 (6)	0.0045 (6)	0.0013 (6)
C7	0.0172 (7)	0.0158 (7)	0.0178 (8)	0.0002 (6)	0.0018 (6)	−0.0018 (6)
C8	0.0202 (8)	0.0231 (8)	0.0142 (7)	0.0014 (6)	0.0062 (6)	−0.0019 (6)
C9	0.0184 (8)	0.0220 (8)	0.0142 (7)	−0.0011 (6)	0.0046 (6)	0.0032 (6)
C10	0.0184 (7)	0.0155 (7)	0.0166 (8)	0.0003 (6)	0.0045 (6)	0.0024 (6)
C12	0.0444 (11)	0.0174 (8)	0.0211 (9)	0.0034 (8)	0.0071 (8)	0.0029 (7)
C14	0.0256 (9)	0.0335 (10)	0.0279 (10)	−0.0012 (8)	0.0130 (8)	−0.0089 (8)
C16	0.0206 (8)	0.0214 (8)	0.0195 (8)	−0.0009 (7)	0.0065 (7)	0.0041 (6)
C18	0.0177 (7)	0.0169 (7)	0.0131 (7)	−0.0020 (6)	0.0065 (6)	−0.0016 (6)
C19	0.0187 (8)	0.0188 (8)	0.0153 (8)	0.0006 (6)	0.0045 (6)	0.0017 (6)
C20	0.0171 (8)	0.0222 (8)	0.0168 (8)	−0.0033 (6)	0.0023 (6)	−0.0020 (6)
C21	0.0201 (8)	0.0165 (8)	0.0202 (8)	−0.0042 (6)	0.0081 (7)	−0.0032 (6)
C22	0.0224 (8)	0.0167 (8)	0.0210 (8)	0.0002 (6)	0.0027 (7)	0.0030 (6)
C23	0.0176 (8)	0.0192 (8)	0.0160 (8)	−0.0023 (6)	0.0019 (6)	−0.0010 (6)
C25	0.0274 (9)	0.0163 (8)	0.0425 (11)	−0.0036 (7)	0.0091 (8)	0.0043 (8)
C26	0.0191 (7)	0.0152 (7)	0.0123 (7)	0.0003 (6)	0.0034 (6)	0.0014 (6)
C27	0.0177 (7)	0.0148 (7)	0.0140 (7)	0.0020 (6)	0.0055 (6)	0.0009 (6)
C28	0.0186 (7)	0.0149 (7)	0.0136 (7)	−0.0018 (6)	0.0036 (6)	0.0025 (6)
C29	0.0256 (8)	0.0164 (8)	0.0131 (7)	−0.0008 (6)	0.0059 (6)	−0.0017 (6)
C30	0.0221 (8)	0.0232 (8)	0.0211 (8)	0.0020 (7)	0.0112 (7)	−0.0024 (7)
C31	0.0166 (7)	0.0218 (8)	0.0204 (8)	−0.0014 (6)	0.0061 (6)	−0.0013 (6)
C33	0.0185 (8)	0.0262 (9)	0.0184 (8)	−0.0038 (7)	0.0058 (6)	−0.0013 (7)
C35	0.0427 (11)	0.0297 (10)	0.0326 (11)	−0.0002 (9)	0.0185 (9)	−0.0140 (8)
N1	0.0182 (6)	0.0146 (6)	0.0133 (6)	0.0000 (5)	0.0054 (5)	0.0021 (5)
O11	0.0282 (6)	0.0153 (6)	0.0218 (6)	0.0027 (5)	0.0078 (5)	−0.0001 (5)
O13	0.0258 (6)	0.0283 (6)	0.0178 (6)	0.0032 (5)	0.0082 (5)	−0.0034 (5)
O15	0.0366 (7)	0.0226 (6)	0.0205 (6)	0.0035 (5)	0.0158 (5)	0.0053 (5)
O17	0.0275 (6)	0.0156 (6)	0.0166 (6)	0.0012 (5)	0.0029 (5)	0.0025 (4)
O24	0.0215 (6)	0.0164 (6)	0.0326 (7)	−0.0058 (5)	0.0047 (5)	0.0010 (5)
O32	0.0183 (6)	0.0221 (6)	0.0168 (6)	−0.0039 (5)	0.0050 (5)	−0.0034 (5)
O34	0.0292 (6)	0.0248 (6)	0.0204 (6)	−0.0031 (5)	0.0105 (5)	−0.0100 (5)

Geometric parameters (Å, º) top

C2—C3	1.532 (2)	C18—C23	1.384 (2)
C2—N1	1.367 (2)	C19—H19	0.9500
C2—O17	1.2117 (19)	C19—C20	1.382 (2)
C3—H3	1.0000	C20—H20	0.9500
C3—C4	1.569 (2)	C20—C21	1.394 (2)
C3—C26	1.501 (2)	C21—C22	1.384 (2)
C4—H4	1.0000	C21—O24	1.3687 (19)
C4—C18	1.501 (2)	C22—H22	0.9500
C4—N1	1.4873 (19)	C22—C23	1.390 (2)
C5—C6	1.391 (2)	C23—H23	0.9500
C5—C10	1.391 (2)	C25—H25A	0.9800
C5—N1	1.4012 (19)	C25—H25B	0.9800
C6—H6	0.9500	C25—H25C	0.9800
C6—C7	1.390 (2)	C25—O24	1.433 (2)
C7—C8	1.396 (2)	C26—C27	1.405 (2)
C7—O11	1.3672 (19)	C26—C31	1.380 (2)
C8—C9	1.396 (2)	C27—H27	0.9500
C8—O13	1.3772 (19)	C27—C28	1.384 (2)
C9—C10	1.386 (2)	C28—C29	1.412 (2)
C9—O15	1.3724 (19)	C28—O32	1.3617 (18)
C10—H10	0.9500	C29—C30	1.374 (2)
C12—H12A	0.9800	C29—O34	1.3709 (19)
C12—H12B	0.9800	C30—H30	0.9500
C12—H12C	0.9800	C30—C31	1.396 (2)
C12—O11	1.428 (2)	C31—H31	0.9500
C14—H14A	0.9800	C33—H33A	0.9800
C14—H14B	0.9800	C33—H33B	0.9800
C14—H14C	0.9800	C33—H33C	0.9800
C14—O13	1.425 (2)	C33—O32	1.4342 (19)
C16—H16A	0.9800	C35—H35A	0.9800
C16—H16B	0.9800	C35—H35B	0.9800
C16—H16C	0.9800	C35—H35C	0.9800
C16—O15	1.4271 (19)	C35—O34	1.428 (2)
C18—C19	1.398 (2)

N1—C2—C3	92.21 (12)	C19—C20—H20	120.0
O17—C2—C3	135.51 (15)	C19—C20—C21	120.02 (15)
O17—C2—N1	132.28 (15)	C21—C20—H20	120.0
C2—C3—H3	109.8	C22—C21—C20	120.09 (15)
C2—C3—C4	85.80 (11)	O24—C21—C20	115.97 (14)
C4—C3—H3	109.8	O24—C21—C22	123.94 (15)
C26—C3—C2	118.68 (13)	C21—C22—H22	120.3
C26—C3—H3	109.8	C21—C22—C23	119.35 (15)
C26—C3—C4	120.91 (13)	C23—C22—H22	120.3
C3—C4—H4	111.1	C18—C23—C22	121.35 (15)
C18—C4—C3	118.07 (13)	C18—C23—H23	119.3
C18—C4—H4	111.1	C22—C23—H23	119.3
N1—C4—C3	86.37 (11)	H25A—C25—H25B	109.5
N1—C4—H4	111.1	H25A—C25—H25C	109.5
N1—C4—C18	116.94 (12)	H25B—C25—H25C	109.5
C6—C5—N1	119.06 (14)	O24—C25—H25A	109.5
C10—C5—C6	121.64 (14)	O24—C25—H25B	109.5
C10—C5—N1	119.28 (14)	O24—C25—H25C	109.5
C5—C6—H6	120.6	C27—C26—C3	120.38 (14)
C7—C6—C5	118.74 (14)	C31—C26—C3	120.59 (14)
C7—C6—H6	120.6	C31—C26—C27	118.99 (14)
C6—C7—C8	120.78 (15)	C26—C27—H27	119.8
O11—C7—C6	123.97 (14)	C28—C27—C26	120.47 (14)
O11—C7—C8	115.24 (14)	C28—C27—H27	119.8
C7—C8—C9	119.01 (14)	C27—C28—C29	119.73 (14)
O13—C8—C7	121.47 (14)	O32—C28—C27	125.56 (14)
O13—C8—C9	119.38 (14)	O32—C28—C29	114.70 (13)
C10—C9—C8	121.05 (14)	C30—C29—C28	119.63 (14)
O15—C9—C8	115.35 (14)	O34—C29—C28	115.20 (14)
O15—C9—C10	123.61 (14)	O34—C29—C30	125.17 (14)
C5—C10—H10	120.7	C29—C30—H30	119.9
C9—C10—C5	118.67 (14)	C29—C30—C31	120.23 (15)
C9—C10—H10	120.7	C31—C30—H30	119.9
H12A—C12—H12B	109.5	C26—C31—C30	120.89 (15)
H12A—C12—H12C	109.5	C26—C31—H31	119.6
H12B—C12—H12C	109.5	C30—C31—H31	119.6
O11—C12—H12A	109.5	H33A—C33—H33B	109.5
O11—C12—H12B	109.5	H33A—C33—H33C	109.5
O11—C12—H12C	109.5	H33B—C33—H33C	109.5
H14A—C14—H14B	109.5	O32—C33—H33A	109.5
H14A—C14—H14C	109.5	O32—C33—H33B	109.5
H14B—C14—H14C	109.5	O32—C33—H33C	109.5
O13—C14—H14A	109.5	H35A—C35—H35B	109.5
O13—C14—H14B	109.5	H35A—C35—H35C	109.5
O13—C14—H14C	109.5	H35B—C35—H35C	109.5
H16A—C16—H16B	109.5	O34—C35—H35A	109.5
H16A—C16—H16C	109.5	O34—C35—H35B	109.5
H16B—C16—H16C	109.5	O34—C35—H35C	109.5
O15—C16—H16A	109.5	C2—N1—C4	95.31 (12)
O15—C16—H16B	109.5	C2—N1—C5	133.20 (13)
O15—C16—H16C	109.5	C5—N1—C4	131.48 (13)
C19—C18—C4	121.98 (14)	C7—O11—C12	117.48 (13)
C23—C18—C4	119.33 (14)	C8—O13—C14	114.77 (13)
C23—C18—C19	118.69 (14)	C9—O15—C16	117.25 (12)
C18—C19—H19	119.8	C21—O24—C25	116.37 (13)
C20—C19—C18	120.48 (15)	C28—O32—C33	117.39 (12)
C20—C19—H19	119.8	C29—O34—C35	116.26 (13)

C2—C3—C4—C18	122.60 (13)	C19—C20—C21—O24	−179.43 (14)
C2—C3—C4—N1	3.87 (10)	C20—C21—C22—C23	−1.0 (2)
C2—C3—C26—C27	49.0 (2)	C20—C21—O24—C25	−179.10 (15)
C2—C3—C26—C31	−128.69 (16)	C21—C22—C23—C18	0.1 (2)
C3—C2—N1—C4	4.44 (12)	C22—C21—O24—C25	0.7 (2)
C3—C2—N1—C5	−176.97 (15)	C23—C18—C19—C20	−1.3 (2)
C3—C4—C18—C19	−51.9 (2)	C26—C3—C4—C18	−116.28 (16)
C3—C4—C18—C23	128.81 (15)	C26—C3—C4—N1	124.99 (14)
C3—C4—N1—C2	−4.35 (12)	C26—C27—C28—C29	1.7 (2)
C3—C4—N1—C5	177.03 (15)	C26—C27—C28—O32	−178.98 (14)
C3—C26—C27—C28	−177.09 (14)	C27—C26—C31—C30	−2.0 (2)
C3—C26—C31—C30	175.73 (14)	C27—C28—C29—C30	−2.7 (2)
C4—C3—C26—C27	−54.3 (2)	C27—C28—C29—O34	177.23 (14)
C4—C3—C26—C31	128.01 (16)	C27—C28—O32—C33	−0.8 (2)
C4—C18—C19—C20	179.34 (14)	C28—C29—C30—C31	1.4 (2)
C4—C18—C23—C22	−179.58 (15)	C28—C29—O34—C35	−165.89 (15)
C5—C6—C7—C8	−0.1 (2)	C29—C28—O32—C33	178.51 (13)
C5—C6—C7—O11	178.70 (14)	C29—C30—C31—C26	1.0 (2)
C6—C5—C10—C9	−1.3 (2)	C30—C29—O34—C35	14.1 (2)
C6—C5—N1—C2	176.19 (16)	C31—C26—C27—C28	0.6 (2)
C6—C5—N1—C4	−5.7 (2)	N1—C2—C3—C4	−4.21 (11)
C6—C7—C8—C9	−2.8 (2)	N1—C2—C3—C26	−127.37 (14)
C6—C7—C8—O13	172.91 (14)	N1—C4—C18—C19	49.1 (2)
C6—C7—O11—C12	−1.0 (2)	N1—C4—C18—C23	−130.20 (15)
C7—C8—C9—C10	3.8 (2)	N1—C5—C6—C7	−179.48 (14)
C7—C8—C9—O15	−176.74 (14)	N1—C5—C10—C9	−179.57 (14)
C7—C8—O13—C14	75.6 (2)	O11—C7—C8—C9	178.24 (14)
C8—C7—O11—C12	177.94 (14)	O11—C7—C8—O13	−6.0 (2)
C8—C9—C10—C5	−1.8 (2)	O13—C8—C9—C10	−172.02 (14)
C8—C9—O15—C16	173.48 (14)	O13—C8—C9—O15	7.4 (2)
C9—C8—O13—C14	−108.73 (17)	O15—C9—C10—C5	178.82 (14)
C10—C5—C6—C7	2.3 (2)	O17—C2—C3—C4	175.09 (18)
C10—C5—N1—C2	−5.5 (2)	O17—C2—C3—C26	51.9 (2)
C10—C5—N1—C4	172.62 (14)	O17—C2—N1—C4	−174.89 (17)
C10—C9—O15—C16	−7.1 (2)	O17—C2—N1—C5	3.7 (3)
C18—C4—N1—C2	−124.13 (14)	O24—C21—C22—C23	179.19 (15)
C18—C4—N1—C5	57.3 (2)	O32—C28—C29—C30	177.87 (14)
C18—C19—C20—C21	0.4 (2)	O32—C28—C29—O34	−2.2 (2)
C19—C18—C23—C22	1.1 (2)	O34—C29—C30—C31	−178.55 (15)
C19—C20—C21—C22	0.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O17	0.95	2.46	3.088 (2)	124
C33—H33A···O13ⁱ	0.98	2.44	3.411 (2)	170
C33—H33A···O15ⁱ	0.98	2.56	3.228 (2)	125

Symmetry code: (i) −x+1, −y+1, −z+1.

4,4-Bis(4-methoxyphenyl)-3-phenyl-1-(3,4,5-trimethoxyphenyl)azetidin-2-one (5) top

Crystal data top

C₃₂H₃₁NO₆	Z = 4
M_r = 525.58	F(000) = 1112
Triclinic, P1	D_x = 1.295 Mg m⁻³
a = 11.5720 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 12.3994 (3) Å	Cell parameters from 9822 reflections
c = 19.9358 (6) Å	θ = 4.0–69.1°
α = 83.779 (1)°	µ = 0.73 mm⁻¹
β = 85.748 (1)°	T = 100 K
γ = 71.559 (1)°	Plate, colourless
V = 2695.23 (13) Å³	0.26 × 0.14 × 0.04 mm

Data collection top

Bruker APEXII Kappa Duo diffractometer	9870 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	8278 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.040
Detector resolution: 8.33 pixels mm^-1	θ_max = 69.2°, θ_min = 3.8°
ω and φ scans	h = −12→13
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −15→14
T_min = 0.695, T_max = 0.753	l = −24→24
37871 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.082P)² + 0.4264P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.137	(Δ/σ)_max < 0.001
S = 1.09	Δρ_max = 0.24 e Å⁻³
9870 reflections	Δρ_min = −0.24 e Å⁻³
714 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00057 (14)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C2	0.45948 (14)	0.12352 (13)	0.41098 (7)	0.0258 (3)
C3	0.50570 (13)	0.00251 (12)	0.38849 (7)	0.0238 (3)
H3	0.509131	−0.055507	0.427887	0.029*
C4	0.37704 (13)	0.03633 (12)	0.35271 (7)	0.0227 (3)
C5	0.24579 (13)	0.24637 (12)	0.37898 (7)	0.0232 (3)
C6	0.13733 (13)	0.23552 (13)	0.36077 (7)	0.0246 (3)
H6	0.133657	0.163916	0.350017	0.030*
C7	0.03343 (13)	0.33081 (13)	0.35836 (7)	0.0247 (3)
C8	0.03928 (13)	0.43662 (12)	0.37288 (7)	0.0249 (3)
C9	0.14979 (14)	0.44524 (12)	0.39159 (7)	0.0248 (3)
C10	0.25432 (13)	0.35051 (13)	0.39515 (7)	0.0243 (3)
H10	0.329209	0.356513	0.408179	0.029*
C12	−0.08797 (14)	0.21821 (13)	0.33449 (8)	0.0302 (3)
H12A	−0.034969	0.184520	0.296552	0.045*
H12B	−0.172727	0.225907	0.326136	0.045*
H12C	−0.063494	0.168771	0.376149	0.045*
C14	−0.14653 (15)	0.54176 (15)	0.42181 (9)	0.0381 (4)
H14A	−0.214092	0.612816	0.414879	0.057*
H14B	−0.106492	0.541914	0.463409	0.057*
H14C	−0.178026	0.476608	0.425514	0.057*
C16	0.25984 (15)	0.56848 (14)	0.41581 (10)	0.0384 (4)
H16A	0.315037	0.549050	0.376144	0.058*
H16B	0.296371	0.519193	0.455526	0.058*
H16C	0.246036	0.648458	0.423381	0.058*
C18	0.28998 (13)	−0.02714 (12)	0.38480 (7)	0.0239 (3)
C19	0.28217 (14)	−0.04663 (13)	0.45531 (7)	0.0268 (3)
H19	0.335945	−0.026095	0.481531	0.032*
C20	0.19842 (14)	−0.09485 (14)	0.48762 (8)	0.0292 (3)
H20	0.195818	−0.107944	0.535467	0.035*
C21	0.11740 (14)	−0.12452 (13)	0.45020 (8)	0.0276 (3)
C22	0.12299 (14)	−0.10582 (13)	0.38041 (8)	0.0290 (3)
H22	0.068320	−0.125593	0.354447	0.035*
C23	0.20890 (14)	−0.05795 (13)	0.34824 (8)	0.0272 (3)
H23	0.212225	−0.046069	0.300346	0.033*
C25	−0.05326 (15)	−0.19440 (15)	0.45198 (8)	0.0346 (4)
H25A	−0.014348	−0.251659	0.420227	0.052*
H25B	−0.101539	−0.123914	0.427085	0.052*
H25C	−0.106692	−0.223322	0.484436	0.052*
C26	0.38961 (12)	0.04393 (12)	0.27645 (7)	0.0224 (3)
C27	0.42081 (14)	−0.05596 (12)	0.24303 (7)	0.0267 (3)
H27	0.431530	−0.127338	0.268706	0.032*
C28	0.43621 (14)	−0.05264 (13)	0.17374 (7)	0.0275 (3)
H28	0.457296	−0.121385	0.152212	0.033*
C29	0.42097 (13)	0.05141 (13)	0.13495 (7)	0.0239 (3)
C30	0.39408 (13)	0.15089 (12)	0.16707 (7)	0.0247 (3)
H30	0.386085	0.221892	0.141444	0.030*
C31	0.37894 (13)	0.14571 (12)	0.23716 (7)	0.0244 (3)
H31	0.360704	0.214143	0.258770	0.029*
C33	0.40625 (16)	0.15099 (13)	0.02546 (8)	0.0322 (3)
H33A	0.416410	0.135899	−0.022220	0.048*
H33B	0.460695	0.193626	0.034783	0.048*
H33C	0.321553	0.195969	0.035415	0.048*
C34	0.62277 (13)	−0.02837 (13)	0.34623 (7)	0.0245 (3)
C35	0.68780 (14)	−0.14197 (13)	0.33960 (8)	0.0298 (3)
H35	0.658822	−0.199750	0.363203	0.036*
C36	0.79423 (15)	−0.17350 (15)	0.29934 (8)	0.0345 (4)
H36	0.836626	−0.251826	0.294889	0.041*
C37	0.83797 (15)	−0.08931 (16)	0.26569 (8)	0.0357 (4)
H37	0.910466	−0.109579	0.237856	0.043*
C38	0.77509 (15)	0.02458 (15)	0.27298 (8)	0.0346 (4)
H38	0.805478	0.082329	0.250588	0.042*
C39	0.66849 (15)	0.05477 (13)	0.31260 (8)	0.0292 (3)
H39	0.626039	0.133131	0.316881	0.035*
N1	0.35155 (11)	0.14964 (10)	0.38044 (6)	0.0229 (3)
O11	−0.07734 (9)	0.32837 (9)	0.34127 (5)	0.0297 (2)
O13	−0.06042 (9)	0.53295 (9)	0.36581 (6)	0.0303 (2)
O15	0.14621 (10)	0.55205 (9)	0.40470 (6)	0.0321 (3)
O17	0.50057 (10)	0.17855 (10)	0.44389 (6)	0.0362 (3)
O24	0.03835 (10)	−0.17149 (10)	0.48725 (5)	0.0338 (3)
O32	0.43557 (10)	0.04515 (9)	0.06690 (5)	0.0278 (2)
C2A	0.53453 (13)	0.41897 (12)	0.09308 (7)	0.0223 (3)
C3A	0.49183 (13)	0.54262 (12)	0.11030 (7)	0.0224 (3)
H3A	0.492800	0.596081	0.069084	0.027*
C4A	0.61774 (13)	0.50903 (12)	0.14866 (7)	0.0216 (3)
C5A	0.74428 (13)	0.29455 (12)	0.13000 (7)	0.0217 (3)
C6A	0.85084 (13)	0.30569 (13)	0.15133 (7)	0.0243 (3)
H6A	0.851693	0.375945	0.165797	0.029*
C7A	0.95683 (13)	0.21244 (13)	0.15129 (7)	0.0245 (3)
C8A	0.95452 (13)	0.10805 (12)	0.13221 (7)	0.0247 (3)
C9A	0.84549 (14)	0.09828 (12)	0.11262 (7)	0.0244 (3)
C10A	0.73910 (13)	0.19127 (12)	0.11059 (7)	0.0242 (3)
H10A	0.665261	0.184581	0.096420	0.029*
C12A	1.07288 (14)	0.32712 (14)	0.17942 (8)	0.0300 (3)
H12D	1.018780	0.356834	0.217905	0.045*
H12E	1.047390	0.378997	0.138755	0.045*
H12F	1.156840	0.321179	0.188543	0.045*
C14A	1.13658 (15)	0.01136 (15)	0.07683 (9)	0.0368 (4)
H14D	1.210710	−0.053961	0.082699	0.055*
H14E	1.158385	0.082093	0.069899	0.055*
H14F	1.094672	0.003889	0.037458	0.055*
C16A	0.73881 (15)	−0.02728 (14)	0.08713 (9)	0.0347 (4)
H16D	0.684824	−0.008542	0.127316	0.052*
H16E	0.754104	−0.107633	0.079924	0.052*
H16F	0.700069	0.021189	0.047667	0.052*
C26A	0.60072 (12)	0.51623 (12)	0.22396 (7)	0.0216 (3)
C31A	0.61578 (13)	0.42025 (12)	0.27005 (7)	0.0245 (3)
H31A	0.640381	0.346634	0.253973	0.029*
C30A	0.59559 (14)	0.43020 (12)	0.33877 (7)	0.0259 (3)
H30A	0.606527	0.363789	0.369355	0.031*
C29A	0.55924 (13)	0.53756 (12)	0.36301 (7)	0.0231 (3)
C28A	0.54078 (13)	0.63421 (12)	0.31783 (7)	0.0249 (3)
H28A	0.513964	0.707941	0.333806	0.030*
C27A	0.56175 (14)	0.62245 (12)	0.24916 (7)	0.0250 (3)
H27A	0.549064	0.689006	0.218549	0.030*
C33A	0.50372 (15)	0.64958 (13)	0.45788 (7)	0.0292 (3)
H33D	0.567288	0.686386	0.447766	0.044*
H33E	0.489437	0.639710	0.506905	0.044*
H33F	0.428160	0.697423	0.437099	0.044*
C18A	0.71158 (13)	0.56193 (12)	0.11335 (7)	0.0228 (3)
C23A	0.78448 (14)	0.60614 (13)	0.14767 (7)	0.0266 (3)
H23A	0.772010	0.609585	0.195132	0.032*
C22A	0.87563 (14)	0.64558 (13)	0.11385 (8)	0.0280 (3)
H22A	0.924198	0.675596	0.138215	0.034*
C21A	0.89479 (13)	0.64071 (12)	0.04483 (7)	0.0263 (3)
C20A	0.82355 (14)	0.59507 (13)	0.00985 (7)	0.0272 (3)
H20A	0.837117	0.590360	−0.037483	0.033*
C19A	0.73369 (13)	0.55683 (12)	0.04369 (7)	0.0256 (3)
H19A	0.685758	0.526369	0.019150	0.031*
C25A	1.06280 (15)	0.71438 (15)	0.04038 (9)	0.0361 (4)
H25D	1.105247	0.652591	0.073325	0.054*
H25E	1.018167	0.781856	0.063803	0.054*
H25F	1.122402	0.733250	0.007567	0.054*
C34A	0.37341 (13)	0.58151 (12)	0.15049 (7)	0.0239 (3)
C35A	0.30917 (14)	0.69713 (13)	0.15043 (8)	0.0296 (3)
H35A	0.338347	0.751051	0.122653	0.036*
C36A	0.20311 (15)	0.73525 (15)	0.19026 (9)	0.0366 (4)
H36A	0.161329	0.814660	0.190374	0.044*
C37A	0.15862 (15)	0.65724 (16)	0.22969 (8)	0.0366 (4)
H37A	0.086319	0.682890	0.257163	0.044*
C38A	0.21981 (15)	0.54132 (15)	0.22907 (8)	0.0350 (4)
H38A	0.188481	0.487557	0.255528	0.042*
C39A	0.32649 (14)	0.50376 (13)	0.18995 (8)	0.0286 (3)
H39A	0.368080	0.424281	0.190017	0.034*
N1A	0.63857 (11)	0.39102 (10)	0.12797 (6)	0.0212 (2)
O11A	1.06653 (9)	0.21689 (9)	0.16931 (5)	0.0295 (2)
O13A	1.05774 (10)	0.01439 (9)	0.13582 (5)	0.0299 (2)
O15A	0.85179 (10)	−0.00808 (9)	0.09658 (6)	0.0296 (2)
O17A	0.49438 (10)	0.36300 (9)	0.06014 (5)	0.0285 (2)
O32A	0.54215 (10)	0.54027 (9)	0.43138 (5)	0.0275 (2)
O24A	0.97899 (10)	0.67854 (10)	0.00599 (5)	0.0330 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0239 (7)	0.0275 (7)	0.0247 (7)	−0.0054 (6)	−0.0024 (6)	−0.0040 (6)
C3	0.0225 (7)	0.0249 (7)	0.0233 (7)	−0.0066 (6)	−0.0039 (6)	0.0001 (5)
C4	0.0218 (7)	0.0220 (7)	0.0229 (7)	−0.0048 (6)	−0.0018 (5)	−0.0019 (5)
C5	0.0238 (7)	0.0249 (7)	0.0189 (7)	−0.0057 (6)	0.0001 (5)	−0.0004 (5)
C6	0.0256 (8)	0.0255 (7)	0.0232 (7)	−0.0086 (6)	−0.0006 (6)	−0.0020 (6)
C7	0.0215 (7)	0.0311 (8)	0.0213 (7)	−0.0083 (6)	0.0000 (5)	−0.0009 (6)
C8	0.0217 (7)	0.0253 (7)	0.0244 (7)	−0.0043 (6)	0.0009 (6)	0.0007 (6)
C9	0.0257 (8)	0.0233 (7)	0.0248 (7)	−0.0077 (6)	0.0025 (6)	−0.0023 (6)
C10	0.0223 (7)	0.0269 (7)	0.0242 (7)	−0.0090 (6)	0.0012 (6)	−0.0018 (6)
C12	0.0269 (8)	0.0326 (8)	0.0338 (8)	−0.0129 (6)	−0.0023 (6)	−0.0029 (6)
C14	0.0256 (8)	0.0368 (9)	0.0468 (10)	−0.0031 (7)	0.0073 (7)	−0.0079 (7)
C16	0.0302 (9)	0.0282 (8)	0.0592 (11)	−0.0113 (7)	−0.0036 (8)	−0.0059 (7)
C18	0.0232 (7)	0.0218 (7)	0.0251 (7)	−0.0044 (6)	−0.0008 (6)	−0.0024 (5)
C19	0.0244 (8)	0.0296 (8)	0.0256 (7)	−0.0072 (6)	−0.0023 (6)	−0.0020 (6)
C20	0.0292 (8)	0.0341 (8)	0.0238 (7)	−0.0097 (6)	0.0012 (6)	−0.0021 (6)
C21	0.0262 (8)	0.0262 (7)	0.0305 (8)	−0.0090 (6)	0.0021 (6)	−0.0022 (6)
C22	0.0298 (8)	0.0289 (8)	0.0304 (8)	−0.0111 (6)	−0.0021 (6)	−0.0047 (6)
C23	0.0290 (8)	0.0278 (7)	0.0249 (7)	−0.0089 (6)	−0.0012 (6)	−0.0028 (6)
C25	0.0307 (9)	0.0407 (9)	0.0374 (9)	−0.0180 (7)	0.0053 (7)	−0.0089 (7)
C26	0.0178 (7)	0.0247 (7)	0.0240 (7)	−0.0058 (5)	−0.0019 (5)	−0.0014 (6)
C27	0.0297 (8)	0.0215 (7)	0.0272 (7)	−0.0054 (6)	−0.0022 (6)	−0.0015 (6)
C28	0.0309 (8)	0.0228 (7)	0.0277 (7)	−0.0062 (6)	0.0000 (6)	−0.0045 (6)
C29	0.0207 (7)	0.0282 (7)	0.0228 (7)	−0.0077 (6)	0.0000 (5)	−0.0031 (6)
C30	0.0255 (7)	0.0219 (7)	0.0266 (7)	−0.0082 (6)	−0.0015 (6)	−0.0001 (6)
C31	0.0257 (7)	0.0227 (7)	0.0256 (7)	−0.0076 (6)	−0.0009 (6)	−0.0047 (6)
C33	0.0455 (10)	0.0272 (8)	0.0244 (7)	−0.0126 (7)	−0.0032 (7)	0.0002 (6)
C34	0.0234 (7)	0.0269 (7)	0.0237 (7)	−0.0079 (6)	−0.0032 (6)	−0.0020 (6)
C35	0.0268 (8)	0.0267 (8)	0.0354 (8)	−0.0086 (6)	−0.0009 (6)	−0.0002 (6)
C36	0.0264 (8)	0.0350 (9)	0.0389 (9)	−0.0040 (7)	−0.0012 (7)	−0.0073 (7)
C37	0.0265 (8)	0.0512 (10)	0.0289 (8)	−0.0114 (7)	0.0024 (6)	−0.0061 (7)
C38	0.0361 (9)	0.0446 (9)	0.0274 (8)	−0.0204 (8)	0.0011 (7)	0.0009 (7)
C39	0.0323 (8)	0.0288 (8)	0.0277 (7)	−0.0114 (6)	−0.0025 (6)	−0.0012 (6)
N1	0.0227 (6)	0.0227 (6)	0.0233 (6)	−0.0061 (5)	−0.0017 (5)	−0.0036 (5)
O11	0.0220 (5)	0.0307 (6)	0.0364 (6)	−0.0073 (4)	−0.0049 (4)	−0.0032 (4)
O13	0.0224 (5)	0.0277 (6)	0.0359 (6)	−0.0023 (4)	0.0010 (4)	0.0003 (4)
O15	0.0260 (6)	0.0236 (5)	0.0470 (7)	−0.0071 (4)	−0.0020 (5)	−0.0061 (5)
O17	0.0315 (6)	0.0352 (6)	0.0413 (6)	−0.0032 (5)	−0.0128 (5)	−0.0143 (5)
O24	0.0328 (6)	0.0420 (7)	0.0313 (6)	−0.0195 (5)	0.0042 (5)	−0.0028 (5)
O32	0.0361 (6)	0.0258 (5)	0.0216 (5)	−0.0100 (4)	0.0004 (4)	−0.0021 (4)
C2A	0.0220 (7)	0.0256 (7)	0.0191 (6)	−0.0077 (6)	−0.0001 (5)	−0.0004 (5)
C3A	0.0224 (7)	0.0237 (7)	0.0210 (7)	−0.0073 (6)	−0.0018 (5)	−0.0001 (5)
C4A	0.0218 (7)	0.0198 (7)	0.0221 (7)	−0.0049 (5)	−0.0014 (5)	−0.0022 (5)
C5A	0.0226 (7)	0.0236 (7)	0.0173 (6)	−0.0060 (6)	0.0009 (5)	0.0002 (5)
C6A	0.0262 (8)	0.0260 (7)	0.0204 (7)	−0.0075 (6)	−0.0004 (6)	−0.0027 (5)
C7A	0.0222 (7)	0.0288 (7)	0.0219 (7)	−0.0079 (6)	0.0004 (5)	−0.0005 (6)
C8A	0.0223 (7)	0.0255 (7)	0.0223 (7)	−0.0030 (6)	0.0021 (6)	−0.0005 (6)
C9A	0.0270 (8)	0.0244 (7)	0.0210 (7)	−0.0076 (6)	0.0022 (6)	−0.0017 (5)
C10A	0.0236 (7)	0.0259 (7)	0.0226 (7)	−0.0076 (6)	0.0012 (6)	−0.0020 (6)
C12A	0.0252 (8)	0.0345 (8)	0.0324 (8)	−0.0116 (6)	−0.0027 (6)	−0.0034 (6)
C14A	0.0262 (8)	0.0363 (9)	0.0417 (9)	−0.0028 (7)	0.0084 (7)	−0.0045 (7)
C16A	0.0305 (9)	0.0277 (8)	0.0475 (10)	−0.0103 (7)	−0.0014 (7)	−0.0068 (7)
C26A	0.0179 (7)	0.0258 (7)	0.0216 (7)	−0.0077 (5)	−0.0010 (5)	−0.0017 (5)
C31A	0.0245 (7)	0.0218 (7)	0.0261 (7)	−0.0063 (6)	0.0011 (6)	−0.0020 (6)
C30A	0.0286 (8)	0.0237 (7)	0.0235 (7)	−0.0073 (6)	0.0003 (6)	0.0017 (6)
C29A	0.0217 (7)	0.0274 (7)	0.0208 (7)	−0.0086 (6)	0.0012 (5)	−0.0032 (6)
C28A	0.0278 (8)	0.0226 (7)	0.0251 (7)	−0.0084 (6)	−0.0009 (6)	−0.0045 (6)
C27A	0.0289 (8)	0.0229 (7)	0.0233 (7)	−0.0087 (6)	−0.0014 (6)	0.0002 (6)
C33A	0.0375 (9)	0.0279 (8)	0.0245 (7)	−0.0131 (7)	0.0043 (6)	−0.0070 (6)
C18A	0.0222 (7)	0.0208 (7)	0.0243 (7)	−0.0056 (5)	−0.0004 (6)	−0.0006 (5)
C23A	0.0289 (8)	0.0294 (8)	0.0226 (7)	−0.0107 (6)	−0.0004 (6)	−0.0020 (6)
C22A	0.0292 (8)	0.0286 (8)	0.0292 (8)	−0.0134 (6)	−0.0019 (6)	−0.0014 (6)
C21A	0.0222 (7)	0.0259 (7)	0.0289 (7)	−0.0068 (6)	0.0015 (6)	0.0023 (6)
C20A	0.0264 (8)	0.0307 (8)	0.0227 (7)	−0.0073 (6)	0.0005 (6)	−0.0001 (6)
C19A	0.0254 (8)	0.0270 (7)	0.0238 (7)	−0.0073 (6)	−0.0022 (6)	−0.0010 (6)
C25A	0.0316 (9)	0.0407 (9)	0.0410 (9)	−0.0203 (7)	0.0042 (7)	−0.0018 (7)
C34A	0.0219 (7)	0.0266 (7)	0.0226 (7)	−0.0063 (6)	−0.0029 (6)	−0.0029 (6)
C35A	0.0257 (8)	0.0277 (8)	0.0342 (8)	−0.0069 (6)	−0.0009 (6)	−0.0018 (6)
C36A	0.0303 (9)	0.0331 (9)	0.0411 (9)	−0.0011 (7)	−0.0009 (7)	−0.0068 (7)
C37A	0.0248 (8)	0.0485 (10)	0.0320 (8)	−0.0047 (7)	0.0049 (6)	−0.0081 (7)
C38A	0.0320 (9)	0.0433 (9)	0.0301 (8)	−0.0146 (7)	0.0046 (7)	−0.0001 (7)
C39A	0.0280 (8)	0.0279 (8)	0.0291 (8)	−0.0083 (6)	0.0010 (6)	−0.0017 (6)
N1A	0.0206 (6)	0.0211 (6)	0.0216 (6)	−0.0056 (5)	−0.0005 (4)	−0.0033 (4)
O11A	0.0222 (5)	0.0310 (6)	0.0350 (6)	−0.0067 (4)	−0.0049 (4)	−0.0030 (4)
O13A	0.0231 (5)	0.0274 (5)	0.0329 (6)	−0.0007 (4)	0.0023 (4)	0.0002 (4)
O15A	0.0273 (6)	0.0230 (5)	0.0380 (6)	−0.0062 (4)	0.0008 (5)	−0.0065 (4)
O17A	0.0287 (6)	0.0288 (5)	0.0296 (5)	−0.0091 (4)	−0.0074 (4)	−0.0054 (4)
O32A	0.0371 (6)	0.0257 (5)	0.0195 (5)	−0.0103 (4)	0.0031 (4)	−0.0030 (4)
O24A	0.0302 (6)	0.0403 (6)	0.0309 (6)	−0.0170 (5)	0.0045 (5)	0.0013 (5)

Geometric parameters (Å, º) top

C2—C3	1.530 (2)	C2A—C3A	1.5240 (19)
C2—N1	1.3600 (19)	C2A—N1A	1.3643 (18)
C2—O17	1.2127 (18)	C2A—O17A	1.2152 (17)
C3—H3	1.0000	C3A—H3A	1.0000
C3—C4	1.6122 (19)	C3A—C4A	1.6105 (19)
C3—C34	1.505 (2)	C3A—C34A	1.5017 (19)
C4—C18	1.5299 (19)	C4A—C26A	1.5080 (18)
C4—C26	1.5119 (19)	C4A—C18A	1.5304 (18)
C4—N1	1.4996 (18)	C4A—N1A	1.5042 (17)
C5—C6	1.382 (2)	C5A—C6A	1.385 (2)
C5—C10	1.399 (2)	C5A—C10A	1.397 (2)
C5—N1	1.4164 (18)	C5A—N1A	1.4142 (18)
C6—H6	0.9500	C6A—H6A	0.9500
C6—C7	1.393 (2)	C6A—C7A	1.394 (2)
C7—C8	1.397 (2)	C7A—C8A	1.397 (2)
C7—O11	1.3608 (17)	C7A—O11A	1.3637 (18)
C8—C9	1.397 (2)	C8A—C9A	1.392 (2)
C8—O13	1.3760 (17)	C8A—O13A	1.3776 (18)
C9—C10	1.394 (2)	C9A—C10A	1.395 (2)
C9—O15	1.3649 (18)	C9A—O15A	1.3689 (18)
C10—H10	0.9500	C10A—H10A	0.9500
C12—H12A	0.9800	C12A—H12D	0.9800
C12—H12B	0.9800	C12A—H12E	0.9800
C12—H12C	0.9800	C12A—H12F	0.9800
C12—O11	1.4310 (18)	C12A—O11A	1.4282 (19)
C14—H14A	0.9800	C14A—H14D	0.9800
C14—H14B	0.9800	C14A—H14E	0.9800
C14—H14C	0.9800	C14A—H14F	0.9800
C14—O13	1.4294 (19)	C14A—O13A	1.4303 (19)
C16—H16A	0.9800	C16A—H16D	0.9800
C16—H16B	0.9800	C16A—H16E	0.9800
C16—H16C	0.9800	C16A—H16F	0.9800
C16—O15	1.4290 (19)	C16A—O15A	1.4299 (19)
C18—C19	1.401 (2)	C26A—C31A	1.395 (2)
C18—C23	1.395 (2)	C26A—C27A	1.387 (2)
C19—H19	0.9500	C31A—H31A	0.9500
C19—C20	1.379 (2)	C31A—C30A	1.385 (2)
C20—H20	0.9500	C30A—H30A	0.9500
C20—C21	1.397 (2)	C30A—C29A	1.392 (2)
C21—C22	1.386 (2)	C29A—C28A	1.388 (2)
C21—O24	1.3657 (18)	C29A—O32A	1.3652 (16)
C22—H22	0.9500	C28A—H28A	0.9500
C22—C23	1.396 (2)	C28A—C27A	1.388 (2)
C23—H23	0.9500	C27A—H27A	0.9500
C25—H25A	0.9800	C33A—H33D	0.9800
C25—H25B	0.9800	C33A—H33E	0.9800
C25—H25C	0.9800	C33A—H33F	0.9800
C25—O24	1.4294 (19)	C33A—O32A	1.4329 (17)
C26—C27	1.403 (2)	C18A—C23A	1.393 (2)
C26—C31	1.387 (2)	C18A—C19A	1.398 (2)
C27—H27	0.9500	C23A—H23A	0.9500
C27—C28	1.377 (2)	C23A—C22A	1.398 (2)
C28—H28	0.9500	C22A—H22A	0.9500
C28—C29	1.398 (2)	C22A—C21A	1.382 (2)
C29—C30	1.388 (2)	C21A—C20A	1.397 (2)
C29—O32	1.3621 (17)	C21A—O24A	1.3665 (17)
C30—H30	0.9500	C20A—H20A	0.9500
C30—C31	1.392 (2)	C20A—C19A	1.378 (2)
C31—H31	0.9500	C19A—H19A	0.9500
C33—H33A	0.9800	C25A—H25D	0.9800
C33—H33B	0.9800	C25A—H25E	0.9800
C33—H33C	0.9800	C25A—H25F	0.9800
C33—O32	1.4299 (18)	C25A—O24A	1.4302 (19)
C34—C35	1.387 (2)	C34A—C35A	1.390 (2)
C34—C39	1.391 (2)	C34A—C39A	1.395 (2)
C35—H35	0.9500	C35A—H35A	0.9500
C35—C36	1.390 (2)	C35A—C36A	1.389 (2)
C36—H36	0.9500	C36A—H36A	0.9500
C36—C37	1.389 (2)	C36A—C37A	1.382 (2)
C37—H37	0.9500	C37A—H37A	0.9500
C37—C38	1.387 (3)	C37A—C38A	1.388 (2)
C38—H38	0.9500	C38A—H38A	0.9500
C38—C39	1.383 (2)	C38A—C39A	1.386 (2)
C39—H39	0.9500	C39A—H39A	0.9500

N1—C2—C3	93.66 (11)	N1A—C2A—C3A	93.91 (11)
O17—C2—C3	134.62 (14)	O17A—C2A—C3A	134.56 (13)
O17—C2—N1	131.71 (14)	O17A—C2A—N1A	131.53 (14)
C2—C3—H3	110.9	C2A—C3A—H3A	111.1
C2—C3—C4	85.08 (10)	C2A—C3A—C4A	85.24 (10)
C4—C3—H3	110.9	C4A—C3A—H3A	111.1
C34—C3—C2	117.03 (12)	C34A—C3A—C2A	116.99 (11)
C34—C3—H3	110.9	C34A—C3A—H3A	111.1
C34—C3—C4	119.75 (11)	C34A—C3A—C4A	118.91 (11)
C18—C4—C3	114.51 (11)	C26A—C4A—C3A	113.84 (11)
C26—C4—C3	113.35 (11)	C26A—C4A—C18A	115.44 (11)
C26—C4—C18	115.70 (12)	C18A—C4A—C3A	113.97 (11)
N1—C4—C3	85.36 (10)	N1A—C4A—C3A	85.39 (10)
N1—C4—C18	111.32 (11)	N1A—C4A—C26A	113.61 (11)
N1—C4—C26	112.88 (11)	N1A—C4A—C18A	110.97 (11)
C6—C5—C10	121.83 (14)	C6A—C5A—C10A	121.79 (13)
C6—C5—N1	119.03 (13)	C6A—C5A—N1A	118.52 (13)
C10—C5—N1	119.13 (13)	C10A—C5A—N1A	119.70 (13)
C5—C6—H6	120.4	C5A—C6A—H6A	120.4
C5—C6—C7	119.24 (13)	C5A—C6A—C7A	119.14 (13)
C7—C6—H6	120.4	C7A—C6A—H6A	120.4
C6—C7—C8	120.42 (13)	C6A—C7A—C8A	120.37 (13)
O11—C7—C6	123.47 (13)	O11A—C7A—C6A	123.07 (13)
O11—C7—C8	116.11 (13)	O11A—C7A—C8A	116.55 (13)
C7—C8—C9	119.25 (13)	C9A—C8A—C7A	119.34 (13)
O13—C8—C7	120.89 (13)	O13A—C8A—C7A	120.22 (13)
O13—C8—C9	119.79 (13)	O13A—C8A—C9A	120.37 (13)
C10—C9—C8	121.14 (13)	C8A—C9A—C10A	121.25 (14)
O15—C9—C8	114.82 (13)	O15A—C9A—C8A	114.95 (13)
O15—C9—C10	124.04 (13)	O15A—C9A—C10A	123.80 (13)
C5—C10—H10	120.9	C5A—C10A—H10A	121.0
C9—C10—C5	118.11 (13)	C9A—C10A—C5A	118.07 (13)
C9—C10—H10	120.9	C9A—C10A—H10A	121.0
H12A—C12—H12B	109.5	H12D—C12A—H12E	109.5
H12A—C12—H12C	109.5	H12D—C12A—H12F	109.5
H12B—C12—H12C	109.5	H12E—C12A—H12F	109.5
O11—C12—H12A	109.5	O11A—C12A—H12D	109.5
O11—C12—H12B	109.5	O11A—C12A—H12E	109.5
O11—C12—H12C	109.5	O11A—C12A—H12F	109.5
H14A—C14—H14B	109.5	H14D—C14A—H14E	109.5
H14A—C14—H14C	109.5	H14D—C14A—H14F	109.5
H14B—C14—H14C	109.5	H14E—C14A—H14F	109.5
O13—C14—H14A	109.5	O13A—C14A—H14D	109.5
O13—C14—H14B	109.5	O13A—C14A—H14E	109.5
O13—C14—H14C	109.5	O13A—C14A—H14F	109.5
H16A—C16—H16B	109.5	H16D—C16A—H16E	109.5
H16A—C16—H16C	109.5	H16D—C16A—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16A—H16F	109.5
O15—C16—H16A	109.5	O15A—C16A—H16D	109.5
O15—C16—H16B	109.5	O15A—C16A—H16E	109.5
O15—C16—H16C	109.5	O15A—C16A—H16F	109.5
C19—C18—C4	118.84 (13)	C31A—C26A—C4A	122.78 (12)
C23—C18—C4	123.58 (13)	C27A—C26A—C4A	119.41 (12)
C23—C18—C19	117.31 (13)	C27A—C26A—C31A	117.71 (13)
C18—C19—H19	119.2	C26A—C31A—H31A	119.4
C20—C19—C18	121.69 (14)	C30A—C31A—C26A	121.29 (13)
C20—C19—H19	119.2	C30A—C31A—H31A	119.4
C19—C20—H20	119.9	C31A—C30A—H30A	120.0
C19—C20—C21	120.22 (14)	C31A—C30A—C29A	119.96 (13)
C21—C20—H20	119.9	C29A—C30A—H30A	120.0
C22—C21—C20	119.23 (14)	C28A—C29A—C30A	119.59 (13)
O24—C21—C20	115.35 (13)	O32A—C29A—C30A	116.48 (12)
O24—C21—C22	125.42 (14)	O32A—C29A—C28A	123.92 (13)
C21—C22—H22	120.0	C29A—C28A—H28A	120.2
C21—C22—C23	120.04 (14)	C29A—C28A—C27A	119.57 (13)
C23—C22—H22	120.0	C27A—C28A—H28A	120.2
C18—C23—C22	121.51 (14)	C26A—C27A—C28A	121.85 (13)
C18—C23—H23	119.2	C26A—C27A—H27A	119.1
C22—C23—H23	119.2	C28A—C27A—H27A	119.1
H25A—C25—H25B	109.5	H33D—C33A—H33E	109.5
H25A—C25—H25C	109.5	H33D—C33A—H33F	109.5
H25B—C25—H25C	109.5	H33E—C33A—H33F	109.5
O24—C25—H25A	109.5	O32A—C33A—H33D	109.5
O24—C25—H25B	109.5	O32A—C33A—H33E	109.5
O24—C25—H25C	109.5	O32A—C33A—H33F	109.5
C27—C26—C4	119.73 (12)	C23A—C18A—C4A	123.46 (12)
C31—C26—C4	122.80 (13)	C23A—C18A—C19A	117.62 (13)
C31—C26—C27	117.35 (13)	C19A—C18A—C4A	118.67 (12)
C26—C27—H27	119.3	C18A—C23A—H23A	119.3
C28—C27—C26	121.34 (13)	C18A—C23A—C22A	121.49 (13)
C28—C27—H27	119.3	C22A—C23A—H23A	119.3
C27—C28—H28	119.8	C23A—C22A—H22A	120.1
C27—C28—C29	120.31 (13)	C21A—C22A—C23A	119.75 (14)
C29—C28—H28	119.8	C21A—C22A—H22A	120.1
C30—C29—C28	119.35 (13)	C22A—C21A—C20A	119.42 (13)
O32—C29—C28	115.42 (13)	O24A—C21A—C22A	125.27 (14)
O32—C29—C30	125.22 (13)	O24A—C21A—C20A	115.31 (13)
C29—C30—H30	120.3	C21A—C20A—H20A	119.8
C29—C30—C31	119.43 (13)	C19A—C20A—C21A	120.31 (14)
C31—C30—H30	120.3	C19A—C20A—H20A	119.8
C26—C31—C30	122.15 (13)	C18A—C19A—H19A	119.3
C26—C31—H31	118.9	C20A—C19A—C18A	121.41 (14)
C30—C31—H31	118.9	C20A—C19A—H19A	119.3
H33A—C33—H33B	109.5	H25D—C25A—H25E	109.5
H33A—C33—H33C	109.5	H25D—C25A—H25F	109.5
H33B—C33—H33C	109.5	H25E—C25A—H25F	109.5
O32—C33—H33A	109.5	O24A—C25A—H25D	109.5
O32—C33—H33B	109.5	O24A—C25A—H25E	109.5
O32—C33—H33C	109.5	O24A—C25A—H25F	109.5
C35—C34—C3	120.19 (13)	C35A—C34A—C3A	120.34 (13)
C35—C34—C39	118.17 (14)	C35A—C34A—C39A	118.31 (14)
C39—C34—C3	121.64 (14)	C39A—C34A—C3A	121.34 (13)
C34—C35—H35	119.1	C34A—C35A—H35A	119.4
C34—C35—C36	121.72 (15)	C36A—C35A—C34A	121.21 (15)
C36—C35—H35	119.1	C36A—C35A—H35A	119.4
C35—C36—H36	120.4	C35A—C36A—H36A	120.1
C37—C36—C35	119.30 (16)	C37A—C36A—C35A	119.76 (16)
C37—C36—H36	120.4	C37A—C36A—H36A	120.1
C36—C37—H37	120.2	C36A—C37A—H37A	120.1
C38—C37—C36	119.54 (15)	C36A—C37A—C38A	119.83 (15)
C38—C37—H37	120.2	C38A—C37A—H37A	120.1
C37—C38—H38	119.7	C37A—C38A—H38A	119.9
C39—C38—C37	120.54 (15)	C39A—C38A—C37A	120.20 (15)
C39—C38—H38	119.7	C39A—C38A—H38A	119.9
C34—C39—H39	119.6	C34A—C39A—H39A	119.7
C38—C39—C34	120.72 (15)	C38A—C39A—C34A	120.65 (15)
C38—C39—H39	119.6	C38A—C39A—H39A	119.7
C2—N1—C4	95.90 (11)	C2A—N1A—C4A	95.38 (11)
C2—N1—C5	132.98 (12)	C2A—N1A—C5A	132.40 (12)
C5—N1—C4	130.96 (12)	C5A—N1A—C4A	130.49 (11)
C7—O11—C12	116.43 (12)	C7A—O11A—C12A	116.42 (12)
C8—O13—C14	112.87 (12)	C8A—O13A—C14A	112.31 (12)
C9—O15—C16	116.94 (12)	C9A—O15A—C16A	116.85 (12)
C21—O24—C25	117.60 (12)	C29A—O32A—C33A	117.84 (11)
C29—O32—C33	116.79 (11)	C21A—O24A—C25A	117.25 (12)

C2—C3—C4—C18	−111.46 (12)	C2A—C3A—C4A—C26A	−115.74 (12)
C2—C3—C4—C26	112.82 (12)	C2A—C3A—C4A—C18A	108.99 (12)
C2—C3—C4—N1	−0.12 (9)	C2A—C3A—C4A—N1A	−1.93 (9)
C2—C3—C34—C35	162.12 (14)	C2A—C3A—C34A—C35A	−159.75 (13)
C2—C3—C34—C39	−18.3 (2)	C2A—C3A—C34A—C39A	21.86 (19)
C3—C2—N1—C4	−0.15 (11)	C3A—C2A—N1A—C4A	−2.28 (11)
C3—C2—N1—C5	175.38 (14)	C3A—C2A—N1A—C5A	−168.04 (14)
C3—C4—C18—C19	39.59 (18)	C3A—C4A—C26A—C31A	101.97 (15)
C3—C4—C18—C23	−146.56 (14)	C3A—C4A—C26A—C27A	−74.25 (16)
C3—C4—C26—C27	81.23 (16)	C3A—C4A—C18A—C23A	139.46 (14)
C3—C4—C26—C31	−94.68 (16)	C3A—C4A—C18A—C19A	−46.49 (17)
C3—C4—N1—C2	0.14 (11)	C3A—C4A—N1A—C2A	2.16 (10)
C3—C4—N1—C5	−175.52 (14)	C3A—C4A—N1A—C5A	168.34 (13)
C3—C34—C35—C36	178.00 (14)	C3A—C34A—C35A—C36A	−176.29 (14)
C3—C34—C39—C38	−178.78 (14)	C3A—C34A—C39A—C38A	177.17 (14)
C4—C3—C34—C35	−97.47 (17)	C4A—C3A—C34A—C35A	100.18 (16)
C4—C3—C34—C39	82.12 (17)	C4A—C3A—C34A—C39A	−78.21 (17)
C4—C18—C19—C20	174.58 (14)	C4A—C26A—C31A—C30A	−177.88 (13)
C4—C18—C23—C22	−173.67 (14)	C4A—C26A—C27A—C28A	177.88 (13)
C4—C26—C27—C28	−178.27 (13)	C4A—C18A—C23A—C22A	174.94 (13)
C4—C26—C31—C30	178.18 (13)	C4A—C18A—C19A—C20A	−174.99 (13)
C5—C6—C7—C8	1.3 (2)	C5A—C6A—C7A—C8A	−2.2 (2)
C5—C6—C7—O11	−179.75 (12)	C5A—C6A—C7A—O11A	177.77 (12)
C6—C5—C10—C9	−0.9 (2)	C6A—C5A—C10A—C9A	−0.5 (2)
C6—C5—N1—C2	−160.61 (14)	C6A—C5A—N1A—C2A	158.07 (14)
C6—C5—N1—C4	13.5 (2)	C6A—C5A—N1A—C4A	−3.1 (2)
C6—C7—C8—C9	−1.7 (2)	C6A—C7A—C8A—C9A	0.6 (2)
C6—C7—C8—O13	175.14 (13)	C6A—C7A—C8A—O13A	−176.38 (12)
C6—C7—O11—C12	8.4 (2)	C6A—C7A—O11A—C12A	−8.64 (19)
C7—C8—C9—C10	0.8 (2)	C7A—C8A—C9A—C10A	1.1 (2)
C7—C8—C9—O15	179.97 (13)	C7A—C8A—C9A—O15A	−178.35 (12)
C7—C8—O13—C14	80.37 (17)	C7A—C8A—O13A—C14A	−84.95 (17)
C8—C7—O11—C12	−172.52 (13)	C8A—C7A—O11A—C12A	171.34 (13)
C8—C9—C10—C5	0.4 (2)	C8A—C9A—C10A—C5A	−1.1 (2)
C8—C9—O15—C16	−172.44 (13)	C8A—C9A—O15A—C16A	169.90 (13)
C9—C8—O13—C14	−102.83 (16)	C9A—C8A—O13A—C14A	98.10 (16)
C10—C5—C6—C7	0.0 (2)	C10A—C5A—C6A—C7A	2.2 (2)
C10—C5—N1—C2	20.2 (2)	C10A—C5A—N1A—C2A	−21.8 (2)
C10—C5—N1—C4	−165.69 (13)	C10A—C5A—N1A—C4A	176.95 (12)
C10—C9—O15—C16	6.7 (2)	C10A—C9A—O15A—C16A	−9.5 (2)
C18—C4—C26—C27	−53.94 (18)	C26A—C4A—C18A—C23A	4.9 (2)
C18—C4—C26—C31	130.15 (14)	C26A—C4A—C18A—C19A	178.98 (13)
C18—C4—N1—C2	114.66 (12)	C26A—C4A—N1A—C2A	116.19 (12)
C18—C4—N1—C5	−61.00 (18)	C26A—C4A—N1A—C5A	−77.63 (17)
C18—C19—C20—C21	−0.8 (2)	C26A—C31A—C30A—C29A	0.1 (2)
C19—C18—C23—C22	0.3 (2)	C31A—C26A—C27A—C28A	1.5 (2)
C19—C20—C21—C22	0.5 (2)	C31A—C30A—C29A—C28A	1.5 (2)
C19—C20—C21—O24	−179.92 (14)	C31A—C30A—C29A—O32A	−179.47 (13)
C20—C21—C22—C23	0.1 (2)	C30A—C29A—C28A—C27A	−1.6 (2)
C20—C21—O24—C25	174.79 (14)	C30A—C29A—O32A—C33A	−179.49 (13)
C21—C22—C23—C18	−0.5 (2)	C29A—C28A—C27A—C26A	0.1 (2)
C22—C21—O24—C25	−5.7 (2)	C28A—C29A—O32A—C33A	−0.5 (2)
C23—C18—C19—C20	0.4 (2)	C27A—C26A—C31A—C30A	−1.6 (2)
C26—C4—C18—C19	174.24 (13)	C18A—C4A—C26A—C31A	−123.44 (14)
C26—C4—C18—C23	−11.9 (2)	C18A—C4A—C26A—C27A	60.34 (17)
C26—C4—N1—C2	−113.27 (13)	C18A—C4A—N1A—C2A	−111.77 (12)
C26—C4—N1—C5	71.07 (18)	C18A—C4A—N1A—C5A	54.41 (18)
C26—C27—C28—C29	0.0 (2)	C18A—C23A—C22A—C21A	−0.2 (2)
C27—C26—C31—C30	2.2 (2)	C23A—C18A—C19A—C20A	−0.6 (2)
C27—C28—C29—C30	2.1 (2)	C23A—C22A—C21A—C20A	−0.8 (2)
C27—C28—C29—O32	−178.53 (13)	C23A—C22A—C21A—O24A	178.60 (14)
C28—C29—C30—C31	−2.0 (2)	C22A—C21A—C20A—C19A	1.0 (2)
C28—C29—O32—C33	172.66 (13)	C22A—C21A—O24A—C25A	7.3 (2)
C29—C30—C31—C26	−0.1 (2)	C21A—C20A—C19A—C18A	−0.3 (2)
C30—C29—O32—C33	−8.0 (2)	C20A—C21A—O24A—C25A	−173.35 (14)
C31—C26—C27—C28	−2.1 (2)	C19A—C18A—C23A—C22A	0.8 (2)
C34—C3—C4—C18	130.10 (13)	C34A—C3A—C4A—C26A	2.56 (17)
C34—C3—C4—C26	−5.61 (18)	C34A—C3A—C4A—C18A	−132.71 (13)
C34—C3—C4—N1	−118.56 (13)	C34A—C3A—C4A—N1A	116.37 (12)
C34—C35—C36—C37	1.1 (2)	C34A—C35A—C36A—C37A	−1.4 (2)
C35—C34—C39—C38	0.8 (2)	C35A—C34A—C39A—C38A	−1.3 (2)
C35—C36—C37—C38	0.2 (2)	C35A—C36A—C37A—C38A	−0.3 (3)
C36—C37—C38—C39	−1.0 (2)	C36A—C37A—C38A—C39A	1.1 (3)
C37—C38—C39—C34	0.5 (2)	C37A—C38A—C39A—C34A	−0.4 (2)
C39—C34—C35—C36	−1.6 (2)	C39A—C34A—C35A—C36A	2.1 (2)
N1—C2—C3—C4	0.14 (10)	N1A—C2A—C3A—C4A	2.13 (10)
N1—C2—C3—C34	121.15 (13)	N1A—C2A—C3A—C34A	−118.01 (12)
N1—C4—C18—C19	−55.13 (17)	N1A—C4A—C26A—C31A	6.39 (19)
N1—C4—C18—C23	118.71 (15)	N1A—C4A—C26A—C27A	−169.83 (12)
N1—C4—C26—C27	176.19 (12)	N1A—C4A—C18A—C23A	−126.17 (14)
N1—C4—C26—C31	0.28 (19)	N1A—C4A—C18A—C19A	47.89 (17)
N1—C5—C6—C7	−179.12 (12)	N1A—C5A—C6A—C7A	−177.72 (12)
N1—C5—C10—C9	178.29 (12)	N1A—C5A—C10A—C9A	179.37 (12)
O11—C7—C8—C9	179.26 (12)	O11A—C7A—C8A—C9A	−179.38 (12)
O11—C7—C8—O13	−3.93 (19)	O11A—C7A—C8A—O13A	3.65 (19)
O13—C8—C9—C10	−176.03 (12)	O13A—C8A—C9A—C10A	178.07 (12)
O13—C8—C9—O15	3.12 (19)	O13A—C8A—C9A—O15A	−1.38 (19)
O15—C9—C10—C5	−178.64 (13)	O15A—C9A—C10A—C5A	178.26 (12)
O17—C2—C3—C4	179.89 (18)	O17A—C2A—C3A—C4A	−177.17 (16)
O17—C2—C3—C34	−59.1 (2)	O17A—C2A—C3A—C34A	62.7 (2)
O17—C2—N1—C4	−179.91 (17)	O17A—C2A—N1A—C4A	177.05 (15)
O17—C2—N1—C5	−4.4 (3)	O17A—C2A—N1A—C5A	11.3 (3)
O24—C21—C22—C23	−179.42 (14)	O32A—C29A—C28A—C27A	179.42 (13)
O32—C29—C30—C31	178.64 (13)	O24A—C21A—C20A—C19A	−178.42 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O17	0.95	2.53	3.1190 (19)	120
C19—H19···O17ⁱ	0.95	2.63	3.2357 (18)	122
C33—H33A···O32ⁱⁱ	0.98	2.56	3.2110 (19)	124
C33—H33B···O17A	0.98	2.37	3.2593 (18)	151
C10A—H10A···O17A	0.95	2.53	3.1158 (18)	120
C33A—H33E···O32Aⁱⁱⁱ	0.98	2.55	3.1918 (18)	123

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z+1.

Extra geometric parameters (°) for 1–5 top

	1	2		3	4	5
A\|B plane normals	13.17 (9)	7.64 (13)	2.62 (13)	12.20 (19)	6.56 (13)	17.08 (9)	15.89 (8)
A\|C plane normals	84.68 (6)	83.59 (9)	83.84 (9)	89.56 (8)	89.15 (6)	89.23 (6) 67.36 (6)	85.80 (6) 63.60 (6)
A\|D plane normals	88.41 (7)	85.72 (9)	63.03 (8)	53.23 (10)	86.00 (7)	69.26 (5)	73.37 (5)
Chirality C3	S	S	R	S	S	R	S
Chirality C4	R	S	R	R	R	–	–
H3—C3—C4—C18^†	6.26	-7.27	10.42	4.38	13.08	-0.98	-1.82
H4—C4—C3—C26^†	8.22	-8.69	12.21	4.96	13.76
C2—N1—C5—C10	-4.3 (3)	-9.4 (3)	3.8 (4)	10.3 (4)	-5.5 (2)	20.2 (2)	-21.8 (2)

† Riding hydrogen atom used in torsion angle, no associated s.u.

Hydrogen-bond geometry (Å, °) for 1–5 top

D—H···A	D—H	H···A	D···A	D—H···A
1
C10—H10···O17	0.95	2.46	3.091 (2)	123
C12—H12C···O11ⁱ	0.98	2.48	3.243 (2)	135
Symmetry codes: (i) -x + 1, -y + 1, -z + 2.

2
C10—H10···O17	0.95	2.50	3.103 (3)	122
C12—H12C···O11ⁱ	0.98	2.48	3.171 (3)	127
C12—H12C···.O13ⁱ	0.98	2.55	3.482 (3)	159
C22—H22···O24Aⁱⁱ	0.95	2.39	3.143 (3)	136
C10A—H10A···O17A	0.95	2.53	3.144 (3)	123
C22A—H22A···O24ⁱⁱⁱ	0.95	2.40	3.274 (3)	153
Symmetry codes: (i) -x + 1, -y, -z + 1; (ii) x + 1, y - 1, z; (iii) x - 1, y, z.

3
C4—H4···O13ⁱ	1.00	2.41	3.396 (3)	171
C10—H10···O17	0.95	2.50	3.105 (3)	122
C16—H16B···O17ⁱⁱ	0.98	2.53	3.387 (3)	146
C27—H27···O17	0.95	2.46	3.156 (3)	131
Symmetry codes: (i) -x + 1, -y + 2, -z + 1; (ii) -x + 1, -y + 2, -z.

4
C10—H10···O17	0.95	2.46	3.088 (2)	124
C33—H33A···O13ⁱ	0.98	2.44	3.411 (2)	170
C33—H33A···O15ⁱ	0.98	2.56	3.228 (2)	125
Symmetry code: (i) -x + 1, -y + 1, -z + 1.

5
C10—H10···O17	0.95	2.53	3.119 (2)	120
C19—H19···O17ⁱ	0.95	2.63	3.236 (2)	122
C33—H33A···O32ⁱⁱ	0.98	2.56	3.211 (2)	124
C33—H33B···O17A	0.98	2.37	3.259 (2)	151
C10A—H10A···O17A	0.95	2.53	3.116 (2)	120
C33A—H33E···O32Aⁱⁱⁱ	0.98	2.55	3.192 (2)	123
Symmetry codes: (i) -x + 1, -y, 1 - z; (ii) -x + 1, -y, -z; (iii) -x + 1, -y + 1, -z + 1.

Database Survey top

CSD Refcode	Reference	CSD Refcode	Reference

PUKNUH	Malebari et al. (2020)	AHERUA	Usman et al. (2002)
PUKPAP	Malebari et al. (2020)	BAGREI	Wang et al. (2011)
PUKPET	Malebari et al. (2020)	DAXKIZ	Piens et al. (2017)
PUKPIX	Malebari et al. (2020)	FEKRUK	Yoshimura et al. (2012)
PUKPOD	Malebari et al. (2020)	FOMBOB, FOMBUH	Chen et al. (2019b)
KAKTIB	O'Boyle et al. (2010)	GADHUO	Alcaide et al. (1987)
KIFZIL	Alborz et al. (2018)	GADJAW	Alcaide et al. (1987)
NARWIO	O'Boyle et al. (2011a)	IFOSII	Gao et al. (2018)
OSOWAV	O'Boyle et al. (2011b)	JAGLEI	Sekine et al. (1989)
OSOWEZ	O'Boyle et al. (2011b)	KAHWIA01	Natarajan et al. (2005)
OSOWID	O'Boyle et al. (2011b)	MIMLIE, MIMLOK, MIMROQ	Cheng & Cheng (2007)
REFDOY	Fu et al. (2017)	NAZHOM	Natarajan et al. (2005)
XALYAN	Malebari et al. (2017)	PADYAU	Kohmoto et al. (1992)
XAMLUV	Malebari et al. (2017)	PIHVEK	Martinez-Cuezva et al. (2018)
XAMMAC	Malebari et al. (2017)	PIVHEK01	Martinez-Cuezva et al. (2019)
XAMMEG	Malebari et al. (2017)	POFWEP	Chen et al. (2019a)
ZUWVUK	Greene et al. (2016)	POWMOD	Toda et al. (1997)
ZUWWAR	Greene et al. (2016)	QULNUH	Minato et al. (2009)
ZUWWEV	Greene et al. (2016)	REBKIS	Palomo et al. (1997)
ZUWWIZ	Greene et al. (2016)	RIFYIO	Zaragoza & Zahn (1995)
ZUWWOF	Greene et al. (2016)	TIVBEH	Mandler et al. (2014)
ZUWWUL	Greene et al. (2016)	YUDKEP	Bandyopadhyay (2015)
ZUWXAS	Greene et al. (2016)	ZOHPAN	Hashizume et al. (1996)
ZUWXEW	Greene et al. (2016)

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Azetidin-2-ones: structures of anti­mitotic compounds based on the 1-(3,4,5-tri­meth­oxy­phen­yl)azetidin-2-one core

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Azetidin-2-ones: structures of antimitotic compounds based on the 1-(3,4,5-trimethoxyphenyl)azetidin-2-one core