The unusual (syn-/anti-)₂ conformation of a di­meth­oxy­pyrimidyl-based tennimide

The tennimide macrocycle (I) resides on a twofold axis and adopts an alternate (syn/anti)₂ conformation with no inner cavity (niche), unlike all previously reported (syn)₄ tennimide conformations. A partial occupancy water mol­ecule (with 0.167 site occupancy) at hydrogen-bonding distances to two symmetry-related carbonyl O atoms (as O—H...O=C) resides on the twofold axis in a mol­ecular niche between two of the pyridine rings. Macrocycle aggregation occurs as one-dimensional chains along the (010) direction.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.054
• wR factor = 0.159
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full value (too) Low ......      61.08 Degree

Author Response: The crystal was initially examined using Mo radiation to 0.80 Angstroms (26 degrees) but this crystal only diffracted to a diffraction limit of 1.30 Angstroms with an average F2 of 6.5. This, however, was sufficient to solve and refine the structure to a final R-factor with R = 0.075. It was noted at this stage that the macrocycle was not disordered.

 A second dataset was collected to 0.88\%A (120 degrees using Cu radiation)
 and taking into account geometric considerations for the diffractometer.
 The diffraction limit for this dataset was 0.96 Angstroms with a redundancy
 of 3.1 and average F2 value of 11.5. The crystal structure then refined
 without problems to R = 0.054. The improvement using Cu data was obvious
 with reflections that were on average twice as intense compared to that
 from using Mo radiation. We regard the R-factor of 5%, low esd's and low
 residual electron density as a satisfactory result for a large macrocycle
 with structural data collected at room temperature.


Alert level B
PLAT245_ALERT_2_B U(iso) H1W       Smaller than U(eq) O1W       by      0.078 Ang   2

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5811
PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6]..       0.58 Ang-1
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       O1W      0.178 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00438 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.739 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.581         62 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3 Note
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          3 Report
PLAT300_ALERT_4_G Atom Site Occupancy of O1W        Constrained at      0.167 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1W        Constrained at      0.167 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       0.50 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.3 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   1 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   6 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

   1 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
   8 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

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT14/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL14/6 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020) and Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL14/6 (Sheldrick, 2015b).

3,11,19,27-Tetrakis(4,6-dimethoxypyrimidin-2-yl)-3,11,19,27,33,34,35,36-\ octaazapentacyclo[27.3.1.1^5,9.1^13,17.1^21,25]hexatriaconta-\ 1(33),5,7,9(36),13(35),14,16,21(34),22,24,29,31-dodecaen-\ 2,4,10,12,18,20,26,28-octone 0.167-hydrate

Crystal data

C52H40N16O16·0.167H2O	Dx = 1.395 Mg m^−3
Mr = 1148.02	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbcn	Cell parameters from 2330 reflections
a = 18.8065 (10) Å	θ = 2.8–63.6°
b = 10.0745 (6) Å	µ = 0.91 mm^−1
c = 28.847 (3) Å	T = 294 K
V = 5465.6 (7) Å^3	Plate, colourless
Z = 4	0.39 × 0.30 × 0.04 mm
F(000) = 2374.7

Data collection

Xcalibur, Sapphire3, Gemini Ultra diffractometer	3036 reflections with I > 2σ(I)
Radiation source: Enhance Ultra (Cu) X-ray Source	Rint = 0.038
Mirror monochromator	θmax = 63.6°, θmin = 3.1°
ω scans	h = −19→21
Absorption correction: analytical (ABSFAC; Clark & Reid, 1998)	k = −6→11
Tmin = 0.778, Tmax = 0.973	l = −33→30
14675 measured reflections	2330 standard reflections every 60 min
4439 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: inferred from neighbouring sites
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.159	w = 1/[σ^2(Fo^2) + (0.0686P)^2 + 1.3472P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4439 reflections	Δρmax = 0.19 e Å^−3
392 parameters	Δρmin = −0.18 e Å^−3
3 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00055 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.05721 (12)	0.3212 (2)	0.40663 (8)	0.0750 (6)
C1	−0.03715 (15)	0.3931 (3)	0.37594 (10)	0.0543 (7)
N1	−0.07837 (12)	0.4970 (2)	0.35800 (8)	0.0544 (6)
O2	−0.06477 (11)	0.43970 (19)	0.28185 (7)	0.0598 (5)
C2	−0.07302 (13)	0.5274 (3)	0.30973 (10)	0.0504 (7)
O3	0.22174 (11)	0.6319 (2)	0.29594 (7)	0.0652 (6)
C3	0.16807 (15)	0.6223 (3)	0.31815 (10)	0.0527 (7)
N3	0.13350 (13)	0.7385 (2)	0.33702 (8)	0.0548 (6)
O4	0.11289 (15)	0.9585 (2)	0.32596 (8)	0.0876 (8)
C4	0.11694 (17)	0.8484 (3)	0.31003 (11)	0.0619 (8)
C11	0.13402 (14)	0.4934 (3)	0.33012 (10)	0.0499 (6)
N12	0.06713 (11)	0.4984 (2)	0.34536 (7)	0.0487 (5)
C13	0.03634 (14)	0.3830 (3)	0.35609 (9)	0.0487 (6)
C14	0.07002 (16)	0.2620 (3)	0.35217 (11)	0.0621 (8)
H14	0.0469	0.1839	0.3605	0.074*
C15	0.13824 (17)	0.2597 (3)	0.33575 (13)	0.0738 (10)
H15	0.1622	0.1794	0.3324	0.089*
C16	0.17103 (16)	0.3770 (3)	0.32431 (12)	0.0655 (8)
H16	0.2173	0.3776	0.3129	0.079*
C11A	−0.13160 (16)	0.5612 (3)	0.38435 (10)	0.0612 (8)
N12A	−0.18786 (13)	0.5977 (3)	0.36019 (9)	0.0684 (7)
C13A	−0.2347 (2)	0.6711 (4)	0.38399 (14)	0.0897 (12)
C14A	−0.2263 (2)	0.6991 (5)	0.43042 (14)	0.1027 (14)
H14A	−0.2600	0.7475	0.4469	0.123*
C15A	−0.1659 (2)	0.6523 (4)	0.45107 (12)	0.0858 (11)
N16A	−0.11615 (15)	0.5832 (3)	0.42871 (9)	0.0714 (8)
O13A	−0.29127 (15)	0.7190 (4)	0.36166 (12)	0.1228 (11)
C17A	−0.2926 (3)	0.7082 (6)	0.31264 (19)	0.1275 (18)
H17A	−0.2552	0.7613	0.2996	0.191*
H17B	−0.3377	0.7387	0.3012	0.191*
H17C	−0.2858	0.6171	0.3039	0.191*
O15A	−0.15514 (19)	0.6812 (3)	0.49625 (9)	0.1107 (10)
C18A	−0.0908 (3)	0.6365 (5)	0.51825 (14)	0.1134 (15)
H18A	−0.0829	0.5449	0.5108	0.170*
H18B	−0.0952	0.6462	0.5512	0.170*
H18C	−0.0515	0.6887	0.5074	0.170*
C21	−0.07603 (14)	0.6707 (3)	0.29661 (9)	0.0504 (7)
N22	−0.09433 (12)	0.6954 (2)	0.25293 (8)	0.0502 (6)
C23	−0.09991 (17)	0.8212 (3)	0.23984 (10)	0.0581 (7)
C24	−0.0874 (2)	0.9276 (3)	0.26911 (13)	0.0771 (10)
H24	−0.0937	1.0146	0.2591	0.093*
C25	−0.0652 (2)	0.9002 (3)	0.31365 (13)	0.0816 (11)
H25	−0.0547	0.9689	0.3341	0.098*
C26	−0.05880 (17)	0.7711 (3)	0.32738 (11)	0.0670 (8)
H26	−0.0430	0.7508	0.3571	0.080*
C21A	0.12724 (17)	0.7424 (3)	0.38590 (10)	0.0580 (8)
N22A	0.07257 (14)	0.8089 (2)	0.40337 (9)	0.0644 (7)
C23A	0.06838 (19)	0.8052 (3)	0.44966 (11)	0.0704 (9)
C24A	0.1147 (2)	0.7351 (3)	0.47695 (12)	0.0773 (10)
H24A	0.1097	0.7312	0.5090	0.093*
C25A	0.1687 (2)	0.6709 (3)	0.45415 (12)	0.0705 (9)
N26A	0.17692 (14)	0.6744 (2)	0.40795 (9)	0.0630 (7)
O23A	0.01530 (15)	0.8719 (2)	0.47037 (8)	0.0903 (8)
C27A	−0.0336 (2)	0.9460 (4)	0.44195 (14)	0.1050 (14)
H27A	−0.0076	1.0071	0.4228	0.158*
H27B	−0.0659	0.9944	0.4614	0.158*
H27C	−0.0599	0.8860	0.4226	0.158*
O25A	0.21549 (15)	0.6015 (3)	0.47933 (8)	0.0899 (8)
C28A	0.2726 (2)	0.5372 (5)	0.45500 (16)	0.1113 (15)
H28A	0.2535	0.4717	0.4343	0.167*
H28B	0.3037	0.4950	0.4769	0.167*
H28C	0.2988	0.6019	0.4376	0.167*
O1W	0.0000	0.187 (3)	0.2500	0.180 (15)	0.167
H1W	−0.0358 (4)	0.238 (3)	0.248 (3)	0.100*	0.167

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0701 (14)	0.0827 (15)	0.0721 (14)	−0.0008 (12)	0.0112 (12)	0.0203 (12)
C1	0.0507 (17)	0.0590 (17)	0.0533 (17)	−0.0002 (14)	−0.0006 (13)	−0.0020 (14)
N1	0.0467 (13)	0.0683 (15)	0.0483 (13)	0.0126 (12)	0.0028 (10)	0.0008 (11)
O2	0.0654 (13)	0.0597 (12)	0.0544 (12)	0.0076 (10)	−0.0001 (10)	−0.0033 (10)
C2	0.0391 (15)	0.0606 (17)	0.0515 (16)	0.0028 (13)	−0.0011 (12)	−0.0036 (14)
O3	0.0487 (12)	0.0717 (14)	0.0752 (14)	−0.0099 (10)	−0.0037 (10)	−0.0028 (10)
C3	0.0463 (16)	0.0493 (16)	0.0625 (18)	−0.0019 (13)	−0.0076 (14)	−0.0046 (13)
N3	0.0650 (15)	0.0426 (12)	0.0567 (14)	−0.0054 (11)	−0.0084 (12)	−0.0050 (10)
O4	0.129 (2)	0.0410 (12)	0.0928 (17)	−0.0117 (13)	−0.0023 (15)	−0.0104 (11)
C4	0.072 (2)	0.0402 (16)	0.073 (2)	−0.0086 (14)	0.0004 (16)	−0.0058 (14)
C11	0.0437 (15)	0.0464 (15)	0.0596 (16)	−0.0008 (13)	−0.0039 (13)	−0.0072 (12)
N12	0.0469 (13)	0.0459 (12)	0.0532 (13)	0.0028 (11)	−0.0017 (10)	−0.0055 (10)
C13	0.0459 (15)	0.0459 (15)	0.0541 (16)	−0.0008 (12)	−0.0036 (12)	0.0004 (12)
C14	0.0559 (18)	0.0419 (15)	0.088 (2)	−0.0023 (14)	0.0000 (16)	−0.0003 (14)
C15	0.0575 (19)	0.0411 (16)	0.123 (3)	0.0085 (15)	0.0102 (19)	−0.0078 (17)
C16	0.0487 (17)	0.0519 (17)	0.096 (2)	0.0026 (14)	0.0069 (16)	−0.0086 (15)
C11A	0.0531 (18)	0.072 (2)	0.0581 (19)	0.0104 (16)	0.0079 (14)	−0.0033 (15)
N12A	0.0498 (15)	0.0873 (19)	0.0681 (17)	0.0140 (14)	0.0091 (12)	−0.0036 (14)
C13A	0.068 (2)	0.110 (3)	0.091 (3)	0.029 (2)	0.015 (2)	−0.007 (2)
C14A	0.095 (3)	0.133 (4)	0.080 (3)	0.038 (3)	0.025 (2)	−0.019 (2)
C15A	0.101 (3)	0.095 (3)	0.061 (2)	0.016 (2)	0.015 (2)	−0.0103 (19)
N16A	0.0756 (18)	0.0832 (19)	0.0553 (16)	0.0099 (15)	0.0056 (13)	−0.0074 (13)
O13A	0.0773 (19)	0.177 (3)	0.114 (2)	0.062 (2)	0.0076 (17)	−0.011 (2)
C17A	0.092 (3)	0.164 (5)	0.126 (4)	0.048 (3)	−0.036 (3)	−0.026 (4)
O15A	0.147 (3)	0.124 (2)	0.0608 (16)	0.022 (2)	0.0187 (17)	−0.0204 (15)
C18A	0.145 (4)	0.128 (4)	0.067 (3)	0.002 (3)	−0.006 (3)	−0.008 (2)
C21	0.0460 (15)	0.0531 (16)	0.0520 (16)	−0.0005 (13)	0.0010 (12)	−0.0060 (13)
N22	0.0504 (13)	0.0455 (13)	0.0547 (14)	0.0051 (10)	−0.0002 (10)	−0.0015 (10)
C23	0.0652 (19)	0.0432 (16)	0.0660 (19)	0.0025 (14)	0.0029 (15)	−0.0047 (14)
C24	0.097 (3)	0.0496 (18)	0.085 (3)	0.0003 (18)	0.004 (2)	−0.0084 (16)
C25	0.105 (3)	0.064 (2)	0.076 (2)	−0.013 (2)	−0.003 (2)	−0.0195 (18)
C26	0.069 (2)	0.071 (2)	0.0607 (19)	−0.0050 (17)	−0.0029 (16)	−0.0110 (15)
C21A	0.067 (2)	0.0444 (15)	0.0626 (19)	−0.0084 (15)	−0.0097 (16)	−0.0120 (13)
N22A	0.0752 (18)	0.0561 (15)	0.0617 (16)	−0.0021 (13)	−0.0107 (13)	−0.0155 (12)
C23A	0.086 (2)	0.0623 (19)	0.063 (2)	−0.0023 (18)	−0.0076 (18)	−0.0193 (16)
C24A	0.100 (3)	0.074 (2)	0.058 (2)	0.000 (2)	−0.0156 (19)	−0.0111 (17)
C25A	0.082 (2)	0.0599 (19)	0.070 (2)	−0.0039 (17)	−0.0193 (19)	−0.0057 (16)
N26A	0.0690 (17)	0.0546 (14)	0.0654 (16)	−0.0052 (13)	−0.0150 (13)	−0.0086 (12)
O23A	0.110 (2)	0.0919 (17)	0.0689 (15)	0.0239 (16)	−0.0025 (14)	−0.0257 (13)
C27A	0.112 (3)	0.111 (3)	0.091 (3)	0.039 (3)	−0.015 (3)	−0.039 (2)
O25A	0.0992 (19)	0.0954 (18)	0.0752 (16)	0.0111 (15)	−0.0286 (15)	−0.0032 (13)
C28A	0.103 (3)	0.121 (4)	0.110 (3)	0.033 (3)	−0.026 (3)	−0.004 (3)
O1W	0.17 (3)	0.085 (19)	0.28 (4)	0.000	−0.06 (3)	0.000

Geometric parameters (Å, º)

O1—C1	1.205 (3)	C17A—H17B	0.9600
C1—N1	1.402 (3)	C17A—H17C	0.9600
C1—C13	1.499 (4)	O15A—C18A	1.438 (5)
N1—C11A	1.414 (3)	C18A—H18A	0.9600
N1—C2	1.429 (3)	C18A—H18B	0.9600
O2—C2	1.205 (3)	C18A—H18C	0.9600
C2—C21	1.494 (4)	C21—N22	1.330 (3)
O3—C3	1.200 (3)	C21—C26	1.384 (4)
C3—N3	1.446 (4)	N22—C23	1.327 (3)
C3—C11	1.488 (4)	C23—C24	1.385 (4)
N3—C4	1.389 (4)	C23—C4^i	1.499 (4)
N3—C21A	1.416 (4)	C24—C25	1.379 (5)
O4—C4	1.203 (3)	C24—H24	0.9300
C4—C23^i	1.499 (4)	C25—C26	1.365 (5)
C11—N12	1.333 (3)	C25—H25	0.9300
C11—C16	1.374 (4)	C26—H26	0.9300
N12—C13	1.335 (3)	C21A—N26A	1.322 (4)
C13—C14	1.378 (4)	C21A—N22A	1.326 (4)
C14—C15	1.368 (4)	N22A—C23A	1.338 (4)
C14—H14	0.9300	C23A—O23A	1.343 (4)
C15—C16	1.373 (4)	C23A—C24A	1.370 (5)
C15—H15	0.9300	C24A—C25A	1.373 (5)
C16—H16	0.9300	C24A—H24A	0.9300
C11A—N12A	1.319 (4)	C25A—O25A	1.338 (4)
C11A—N16A	1.331 (4)	C25A—N26A	1.342 (4)
N12A—C13A	1.339 (4)	O23A—C27A	1.441 (4)
C13A—O13A	1.334 (4)	C27A—H27A	0.9600
C13A—C14A	1.378 (5)	C27A—H27B	0.9600
C14A—C15A	1.367 (5)	C27A—H27C	0.9600
C14A—H14A	0.9300	O25A—C28A	1.438 (5)
C15A—N16A	1.332 (4)	C28A—H28A	0.9600
C15A—O15A	1.351 (4)	C28A—H28B	0.9600
O13A—C17A	1.418 (5)	C28A—H28C	0.9600
C17A—H17A	0.9600	O1W—H1W	0.850 (5)
O1—C1—N1	123.2 (3)	H17A—C17A—H17C	109.5
O1—C1—C13	121.9 (3)	H17B—C17A—H17C	109.5
N1—C1—C13	114.8 (2)	C15A—O15A—C18A	119.0 (3)
C1—N1—C11A	122.3 (2)	O15A—C18A—H18A	109.5
C1—N1—C2	118.7 (2)	O15A—C18A—H18B	109.5
C11A—N1—C2	118.4 (2)	H18A—C18A—H18B	109.5
O2—C2—N1	120.1 (3)	O15A—C18A—H18C	109.5
O2—C2—C21	123.0 (3)	H18A—C18A—H18C	109.5
N1—C2—C21	116.8 (2)	H18B—C18A—H18C	109.5
O3—C3—N3	120.9 (3)	N22—C21—C26	122.1 (3)
O3—C3—C11	123.8 (3)	N22—C21—C2	115.5 (2)
N3—C3—C11	115.2 (3)	C26—C21—C2	122.3 (3)
C4—N3—C21A	121.2 (2)	C23—N22—C21	117.9 (2)
C4—N3—C3	122.4 (2)	N22—C23—C24	123.6 (3)
C21A—N3—C3	115.8 (2)	N22—C23—C4^i	117.7 (2)
O4—C4—N3	122.3 (3)	C24—C23—C4^i	118.7 (3)
O4—C4—C23^i	121.4 (3)	C25—C24—C23	117.7 (3)
N3—C4—C23^i	116.1 (2)	C25—C24—H24	121.2
N12—C11—C16	123.4 (3)	C23—C24—H24	121.2
N12—C11—C3	116.7 (2)	C26—C25—C24	119.2 (3)
C16—C11—C3	119.9 (3)	C26—C25—H25	120.4
C11—N12—C13	116.9 (2)	C24—C25—H25	120.4
N12—C13—C14	123.5 (3)	C25—C26—C21	119.3 (3)
N12—C13—C1	115.4 (2)	C25—C26—H26	120.3
C14—C13—C1	121.0 (3)	C21—C26—H26	120.3
C15—C14—C13	118.4 (3)	N26A—C21A—N22A	128.8 (3)
C15—C14—H14	120.8	N26A—C21A—N3	114.0 (3)
C13—C14—H14	120.8	N22A—C21A—N3	117.2 (3)
C14—C15—C16	119.3 (3)	C21A—N22A—C23A	114.3 (3)
C14—C15—H15	120.4	N22A—C23A—O23A	118.3 (3)
C16—C15—H15	120.4	N22A—C23A—C24A	123.4 (3)
C15—C16—C11	118.5 (3)	O23A—C23A—C24A	118.3 (3)
C15—C16—H16	120.7	C23A—C24A—C25A	116.0 (3)
C11—C16—H16	120.7	C23A—C24A—H24A	122.0
N12A—C11A—N16A	129.5 (3)	C25A—C24A—H24A	122.0
N12A—C11A—N1	114.3 (3)	O25A—C25A—N26A	118.5 (3)
N16A—C11A—N1	116.0 (3)	O25A—C25A—C24A	118.2 (3)
C11A—N12A—C13A	114.2 (3)	N26A—C25A—C24A	123.3 (3)
O13A—C13A—N12A	118.5 (4)	C21A—N26A—C25A	114.2 (3)
O13A—C13A—C14A	119.1 (3)	C23A—O23A—C27A	118.7 (3)
N12A—C13A—C14A	122.4 (4)	O23A—C27A—H27A	109.5
C15A—C14A—C13A	116.6 (3)	O23A—C27A—H27B	109.5
C15A—C14A—H14A	121.7	H27A—C27A—H27B	109.5
C13A—C14A—H14A	121.7	O23A—C27A—H27C	109.5
N16A—C15A—O15A	118.3 (4)	H27A—C27A—H27C	109.5
N16A—C15A—C14A	123.6 (3)	H27B—C27A—H27C	109.5
O15A—C15A—C14A	118.1 (3)	C25A—O25A—C28A	117.5 (3)
C11A—N16A—C15A	113.5 (3)	O25A—C28A—H28A	109.5
C13A—O13A—C17A	117.9 (3)	O25A—C28A—H28B	109.5
O13A—C17A—H17A	109.5	H28A—C28A—H28B	109.5
O13A—C17A—H17B	109.5	O25A—C28A—H28C	109.5
H17A—C17A—H17B	109.5	H28A—C28A—H28C	109.5
O13A—C17A—H17C	109.5	H28B—C28A—H28C	109.5
O1—C1—N1—C11A	26.2 (4)	C13A—C14A—C15A—N16A	0.4 (7)
C13—C1—N1—C11A	−150.1 (3)	C13A—C14A—C15A—O15A	178.3 (4)
O1—C1—N1—C2	−145.4 (3)	N12A—C11A—N16A—C15A	0.1 (5)
C13—C1—N1—C2	38.4 (3)	N1—C11A—N16A—C15A	175.5 (3)
C1—N1—C2—O2	35.9 (4)	O15A—C15A—N16A—C11A	−179.4 (3)
C11A—N1—C2—O2	−136.0 (3)	C14A—C15A—N16A—C11A	−1.5 (6)
C1—N1—C2—C21	−142.4 (3)	N12A—C13A—O13A—C17A	−10.2 (6)
C11A—N1—C2—C21	45.7 (3)	C14A—C13A—O13A—C17A	169.5 (5)
O3—C3—N3—C4	51.6 (4)	N16A—C15A—O15A—C18A	0.0 (6)
C11—C3—N3—C4	−131.0 (3)	C14A—C15A—O15A—C18A	−178.0 (4)
O3—C3—N3—C21A	−119.2 (3)	O2—C2—C21—N22	23.0 (4)
C11—C3—N3—C21A	58.3 (3)	N1—C2—C21—N22	−158.8 (2)
C21A—N3—C4—O4	17.8 (5)	O2—C2—C21—C26	−155.0 (3)
C3—N3—C4—O4	−152.5 (3)	N1—C2—C21—C26	23.2 (4)
C21A—N3—C4—C23^i	−158.6 (3)	C26—C21—N22—C23	−3.9 (4)
C3—N3—C4—C23^i	31.1 (4)	C2—C21—N22—C23	178.0 (2)
O3—C3—C11—N12	−165.0 (3)	C21—N22—C23—C24	0.3 (5)
N3—C3—C11—N12	17.6 (4)	C21—N22—C23—C4^i	177.0 (3)
O3—C3—C11—C16	13.7 (4)	N22—C23—C24—C25	2.7 (5)
N3—C3—C11—C16	−163.7 (3)	C4^i—C23—C24—C25	−174.0 (3)
C16—C11—N12—C13	1.3 (4)	C23—C24—C25—C26	−2.1 (6)
C3—C11—N12—C13	179.9 (2)	C24—C25—C26—C21	−1.3 (5)
C11—N12—C13—C14	0.0 (4)	N22—C21—C26—C25	4.5 (5)
C11—N12—C13—C1	176.3 (2)	C2—C21—C26—C25	−177.6 (3)
O1—C1—C13—N12	−141.8 (3)	C4—N3—C21A—N26A	−143.9 (3)
N1—C1—C13—N12	34.4 (3)	C3—N3—C21A—N26A	27.0 (3)
O1—C1—C13—C14	34.5 (4)	C4—N3—C21A—N22A	38.0 (4)
N1—C1—C13—C14	−149.2 (3)	C3—N3—C21A—N22A	−151.2 (2)
N12—C13—C14—C15	−1.1 (5)	N26A—C21A—N22A—C23A	0.1 (4)
C1—C13—C14—C15	−177.1 (3)	N3—C21A—N22A—C23A	178.0 (3)
C13—C14—C15—C16	0.8 (5)	C21A—N22A—C23A—O23A	178.8 (3)
C14—C15—C16—C11	0.4 (5)	C21A—N22A—C23A—C24A	−2.4 (5)
N12—C11—C16—C15	−1.5 (5)	N22A—C23A—C24A—C25A	2.4 (5)
C3—C11—C16—C15	179.9 (3)	O23A—C23A—C24A—C25A	−178.8 (3)
C1—N1—C11A—N12A	−144.5 (3)	C23A—C24A—C25A—O25A	179.7 (3)
C2—N1—C11A—N12A	27.1 (4)	C23A—C24A—C25A—N26A	−0.3 (5)
C1—N1—C11A—N16A	39.5 (4)	N22A—C21A—N26A—C25A	1.8 (4)
C2—N1—C11A—N16A	−148.9 (3)	N3—C21A—N26A—C25A	−176.1 (2)
N16A—C11A—N12A—C13A	2.3 (5)	O25A—C25A—N26A—C21A	178.3 (3)
N1—C11A—N12A—C13A	−173.1 (3)	C24A—C25A—N26A—C21A	−1.7 (5)
C11A—N12A—C13A—O13A	176.2 (4)	N22A—C23A—O23A—C27A	−1.2 (5)
C11A—N12A—C13A—C14A	−3.5 (6)	C24A—C23A—O23A—C27A	179.9 (3)
O13A—C13A—C14A—C15A	−177.3 (4)	N26A—C25A—O25A—C28A	1.3 (5)
N12A—C13A—C14A—C15A	2.3 (7)	C24A—C25A—O25A—C28A	−178.7 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O3^ii	0.93	2.47	3.148 (4)	130
C15—H15···O4^iii	0.93	2.42	3.084 (4)	129
C18A—H18C···O23A	0.96	2.47	3.393 (6)	160
C24—H24···O1W^iv	0.93	2.49	3.14 (2)	127
C26—H26···N22A	0.93	2.62	3.325 (4)	133
C27A—H27B···O23A^v	0.96	2.57	3.144 (4)	119

Symmetry codes: (ii) −x+1/2, y−1/2, z; (iii) x, y−1, z; (iv) x, y+1, z; (v) −x, −y+2, −z+1.