Crystal structure of a methanol solvate of a macrocycle bearing two flexible side-arms

In the crystal structure of di-tert-butyl N,N′-{[13,15,28,30,31,33-hexa­ethyl-3,10,18,25,32,34-hexa­aza­penta­cyclo­[25.3.1.1^5,8.1^12,16.1^20,23]tetra­triaconta-1(31),3,5,7,9,12 (33),13,15,18,20,22,24,27,29-tetra­deca­ene-14,29-di­yl]bis­(methyl­ene)}dicarbamate methanol disolvate, a pair of solvent mol­ecules is located in the cavity of the host mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.038
• wR factor = 0.103
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1A      ..H3       .       2.13 Ang.
                                                      x,y,z  =      1_555 Check
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1       .     Please Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10C     ..O1       .       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22A     ..N4       .       2.73 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         11 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 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
   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


checkCIF publication errors

Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 112
              hexaazapentacyclo[25.3.1.1^{5,8}.1^{12,16}.1^{20,23}]tetratriaconta-\
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 371
              hexaazapentacyclo[25.3.1.1^{5,8}.1^{12,16}.1^{20,23}]tetratriaconta-\
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

   2 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and shelXle (Hübschle et al., 2011).

Di-tert-butyl N,N'-{[13,15,28,30,31,33-hexaethyl-3,10,18,25,32,34-hexaazapentacyclo[25.3.1.1^5,8.1^12,16.1^20,23]tetratriaconta-1(31),3,5,7,9,12(33),13,15,18,20,22,24,27,29-tetradecaene-14,29-diyl]bis(methylene)}dicarbamate methanol disolvate

Crystal data

C52H72N8O4·2CH4O	F(000) = 1016
Mr = 937.26	Dx = 1.194 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.8395 (9) Å	Cell parameters from 4018 reflections
b = 20.0443 (19) Å	θ = 2.6–30.1°
c = 9.6347 (9) Å	µ = 0.08 mm^−1
β = 102.800 (3)°	T = 100 K
V = 2606.3 (4) Å^3	Piece, colorless
Z = 2	0.35 × 0.31 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer	Rint = 0.036
φ and ω scans	θmax = 26.0°, θmin = 3.1°
35355 measured reflections	h = −17→16
5099 independent reflections	k = −24→24
4185 reflections with I > 2σ(I)	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 1.1359P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5099 reflections	Δρmax = 0.32 e Å^−3
326 parameters	Δρmin = −0.24 e Å^−3

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
O1	−0.05242 (7)	0.39730 (5)	0.44678 (10)	0.0227 (2)
O2	−0.09351 (7)	0.36986 (5)	0.21095 (10)	0.0239 (2)
N1	0.05622 (9)	0.34295 (6)	0.35075 (14)	0.0234 (3)
H1	0.0950 (13)	0.3465 (9)	0.437 (2)	0.033 (5)*
N2	0.52052 (8)	0.30374 (6)	0.43228 (12)	0.0185 (3)
N3	0.65652 (8)	0.34838 (6)	0.69247 (12)	0.0161 (2)
H3	0.6091 (13)	0.3752 (9)	0.6721 (18)	0.026 (4)*
N4	0.30737 (8)	0.53752 (6)	0.13277 (12)	0.0176 (2)
C1	0.19144 (10)	0.33253 (7)	0.21758 (14)	0.0171 (3)
C2	0.27938 (10)	0.29697 (7)	0.27053 (14)	0.0167 (3)
C3	0.36923 (10)	0.32070 (7)	0.24387 (14)	0.0163 (3)
C4	0.37244 (10)	0.38170 (7)	0.17394 (14)	0.0163 (3)
C5	0.28382 (10)	0.41619 (7)	0.11840 (14)	0.0163 (3)
C6	0.19328 (10)	0.39170 (7)	0.13994 (14)	0.0164 (3)
C7	0.09242 (10)	0.30690 (7)	0.24027 (15)	0.0210 (3)
H7A	0.042489	0.310462	0.149465	0.025*
H7B	0.099383	0.259096	0.266375	0.025*
C8	−0.03567 (10)	0.37006 (7)	0.32635 (15)	0.0196 (3)
C9	−0.14526 (10)	0.43525 (7)	0.44325 (15)	0.0210 (3)
C10	−0.14381 (12)	0.49841 (8)	0.35766 (17)	0.0267 (3)
H10A	−0.205587	0.523136	0.352617	0.040*
H10B	−0.137439	0.486846	0.261267	0.040*
H10C	−0.087481	0.526152	0.403679	0.040*
C11	−0.23587 (11)	0.39246 (8)	0.38596 (18)	0.0286 (4)
H11A	−0.293766	0.412140	0.413275	0.043*
H11B	−0.224754	0.347377	0.425669	0.043*
H11C	−0.247562	0.390231	0.281954	0.043*
C12	−0.13747 (12)	0.45120 (8)	0.59929 (16)	0.0293 (4)
H12A	−0.195568	0.477016	0.609754	0.044*
H12B	−0.077292	0.477311	0.635484	0.044*
H12C	−0.134509	0.409572	0.653418	0.044*
C13	0.27834 (11)	0.23254 (7)	0.35348 (15)	0.0214 (3)
H13A	0.226010	0.235333	0.408604	0.026*
H13B	0.342760	0.227356	0.421925	0.026*
C14	0.25964 (12)	0.17120 (7)	0.25671 (17)	0.0271 (3)
H14A	0.261688	0.130930	0.314968	0.041*
H14B	0.310878	0.168419	0.201165	0.041*
H14C	0.194388	0.174963	0.192008	0.041*
C15	0.46409 (10)	0.28110 (7)	0.29158 (15)	0.0195 (3)
H15A	0.447814	0.233201	0.296730	0.023*
H15B	0.505554	0.286256	0.220681	0.023*
C16	0.60090 (9)	0.27313 (7)	0.48501 (15)	0.0167 (3)
H16	0.618598	0.236102	0.434316	0.020*
C17	0.66663 (9)	0.29172 (6)	0.61784 (14)	0.0166 (3)
C18	0.75267 (10)	0.25976 (7)	0.68732 (15)	0.0199 (3)
H18	0.778419	0.219307	0.658912	0.024*
C19	0.79463 (10)	0.29810 (7)	0.80710 (15)	0.0199 (3)
H19	0.853574	0.288089	0.875574	0.024*
C20	0.73443 (9)	0.35328 (7)	0.80740 (14)	0.0170 (3)
C21	0.47064 (10)	0.41122 (7)	0.15895 (16)	0.0216 (3)
H21A	0.523104	0.396530	0.240640	0.026*
H21B	0.466421	0.460458	0.163095	0.026*
C22	0.50054 (12)	0.39142 (8)	0.02052 (18)	0.0296 (4)
H22A	0.565586	0.410479	0.019496	0.044*
H22B	0.451306	0.408436	−0.061002	0.044*
H22C	0.503828	0.342693	0.014619	0.044*
C23	0.28733 (10)	0.48040 (7)	0.03607 (14)	0.0188 (3)
H23A	0.339825	0.477093	−0.018671	0.023*
H23B	0.223203	0.487046	−0.032276	0.023*
C24	0.25124 (10)	0.58827 (7)	0.10195 (14)	0.0171 (3)
H24	0.199470	0.587758	0.018667	0.021*
C25	0.09723 (10)	0.42735 (7)	0.07478 (15)	0.0199 (3)
H25A	0.110589	0.475578	0.067138	0.024*
H25B	0.050286	0.422131	0.138050	0.024*
C26	0.04981 (11)	0.39996 (8)	−0.07290 (16)	0.0262 (3)
H26A	−0.013369	0.422704	−0.109625	0.039*
H26B	0.038118	0.351973	−0.066133	0.039*
H26C	0.094315	0.407676	−0.137487	0.039*
O1A	0.45908 (8)	0.40005 (6)	0.59724 (13)	0.0377 (3)
H1A	0.4690 (17)	0.3687 (12)	0.527 (3)	0.067 (7)*
C1A	0.39245 (13)	0.44958 (9)	0.5307 (2)	0.0403 (4)
H1AA	0.384837	0.483417	0.600927	0.060*
H1AB	0.327948	0.429211	0.490507	0.060*
H1AC	0.418223	0.470560	0.454430	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0201 (5)	0.0302 (6)	0.0185 (5)	0.0035 (4)	0.0054 (4)	0.0017 (4)
O2	0.0177 (5)	0.0318 (6)	0.0213 (5)	−0.0018 (4)	0.0021 (4)	−0.0011 (4)
N1	0.0182 (6)	0.0332 (7)	0.0186 (6)	0.0026 (5)	0.0037 (5)	0.0022 (5)
N2	0.0162 (6)	0.0177 (6)	0.0209 (6)	0.0009 (5)	0.0023 (5)	−0.0014 (5)
N3	0.0137 (5)	0.0144 (6)	0.0198 (6)	0.0022 (5)	0.0025 (5)	0.0023 (5)
N4	0.0176 (6)	0.0165 (6)	0.0187 (6)	−0.0022 (5)	0.0041 (5)	0.0010 (5)
C1	0.0167 (6)	0.0190 (7)	0.0159 (6)	−0.0021 (5)	0.0044 (5)	−0.0035 (5)
C2	0.0204 (7)	0.0160 (7)	0.0134 (6)	−0.0005 (5)	0.0031 (5)	−0.0022 (5)
C3	0.0171 (6)	0.0168 (7)	0.0141 (6)	0.0003 (5)	0.0017 (5)	−0.0042 (5)
C4	0.0153 (6)	0.0177 (7)	0.0160 (6)	−0.0019 (5)	0.0035 (5)	−0.0051 (5)
C5	0.0191 (7)	0.0157 (7)	0.0137 (6)	−0.0007 (5)	0.0029 (5)	−0.0031 (5)
C6	0.0160 (6)	0.0180 (7)	0.0147 (6)	0.0006 (5)	0.0022 (5)	−0.0031 (5)
C7	0.0194 (7)	0.0211 (7)	0.0234 (7)	−0.0015 (6)	0.0067 (6)	0.0011 (6)
C8	0.0181 (7)	0.0213 (7)	0.0205 (7)	−0.0035 (5)	0.0067 (6)	0.0028 (6)
C9	0.0172 (7)	0.0228 (7)	0.0240 (7)	0.0024 (6)	0.0069 (6)	0.0028 (6)
C10	0.0291 (8)	0.0247 (8)	0.0264 (8)	−0.0013 (6)	0.0065 (6)	0.0024 (6)
C11	0.0207 (7)	0.0263 (8)	0.0413 (9)	−0.0016 (6)	0.0124 (7)	−0.0009 (7)
C12	0.0296 (8)	0.0366 (9)	0.0241 (8)	0.0057 (7)	0.0107 (6)	0.0029 (7)
C13	0.0223 (7)	0.0211 (7)	0.0210 (7)	0.0006 (6)	0.0048 (6)	0.0041 (6)
C14	0.0307 (8)	0.0193 (7)	0.0310 (8)	−0.0022 (6)	0.0059 (7)	0.0015 (6)
C15	0.0191 (7)	0.0186 (7)	0.0200 (7)	0.0018 (5)	0.0028 (6)	−0.0026 (6)
C16	0.0160 (7)	0.0130 (6)	0.0226 (7)	−0.0007 (5)	0.0075 (5)	−0.0001 (5)
C17	0.0158 (6)	0.0133 (6)	0.0214 (7)	0.0003 (5)	0.0055 (5)	0.0024 (5)
C18	0.0185 (7)	0.0148 (7)	0.0268 (8)	0.0029 (5)	0.0055 (6)	0.0024 (6)
C19	0.0152 (6)	0.0193 (7)	0.0237 (7)	0.0011 (5)	0.0007 (5)	0.0056 (6)
C20	0.0144 (6)	0.0175 (7)	0.0188 (7)	−0.0021 (5)	0.0033 (5)	0.0047 (5)
C21	0.0167 (7)	0.0200 (7)	0.0285 (8)	−0.0033 (5)	0.0055 (6)	−0.0026 (6)
C22	0.0273 (8)	0.0273 (8)	0.0401 (9)	−0.0041 (6)	0.0198 (7)	−0.0029 (7)
C23	0.0196 (7)	0.0191 (7)	0.0172 (7)	−0.0012 (5)	0.0031 (5)	−0.0004 (5)
C24	0.0150 (6)	0.0190 (7)	0.0171 (7)	−0.0028 (5)	0.0032 (5)	0.0043 (5)
C25	0.0173 (7)	0.0198 (7)	0.0224 (7)	0.0019 (6)	0.0038 (5)	0.0030 (6)
C26	0.0203 (7)	0.0320 (9)	0.0241 (8)	0.0010 (6)	0.0000 (6)	0.0044 (6)
O1A	0.0296 (6)	0.0436 (7)	0.0353 (7)	0.0168 (5)	−0.0027 (5)	−0.0147 (6)
C1A	0.0345 (9)	0.0347 (10)	0.0494 (11)	0.0118 (8)	0.0046 (8)	−0.0090 (8)

Geometric parameters (Å, º)

O1—C8	1.3481 (17)	C12—H12C	0.9800
O1—C9	1.4871 (16)	C13—C14	1.530 (2)
O2—C8	1.2176 (17)	C13—H13A	0.9900
N1—C8	1.3548 (18)	C13—H13B	0.9900
N1—C7	1.4636 (19)	C14—H14A	0.9800
N1—H1	0.886 (19)	C14—H14B	0.9800
N2—C16	1.2733 (17)	C14—H14C	0.9800
N2—C15	1.4780 (17)	C15—H15A	0.9900
N3—C20	1.3671 (17)	C15—H15B	0.9900
N3—C17	1.3679 (18)	C16—C17	1.4451 (19)
N3—H3	0.838 (18)	C16—H16	0.9500
N4—C24	1.2744 (17)	C17—C18	1.3868 (19)
N4—C23	1.4632 (17)	C18—C19	1.401 (2)
C1—C2	1.4052 (19)	C18—H18	0.9500
C1—C6	1.4054 (19)	C19—C20	1.3851 (19)
C1—C7	1.5239 (18)	C19—H19	0.9500
C2—C3	1.4071 (19)	C20—C24^i	1.4486 (19)
C2—C13	1.5204 (19)	C21—C22	1.534 (2)
C3—C4	1.4014 (19)	C21—H21A	0.9900
C3—C15	1.5158 (18)	C21—H21B	0.9900
C4—C5	1.4065 (19)	C22—H22A	0.9800
C4—C21	1.5182 (18)	C22—H22B	0.9800
C5—C6	1.4033 (19)	C22—H22C	0.9800
C5—C23	1.5183 (19)	C23—H23A	0.9900
C6—C25	1.5173 (18)	C23—H23B	0.9900
C7—H7A	0.9900	C24—H24	0.9500
C7—H7B	0.9900	C25—C26	1.531 (2)
C9—C10	1.513 (2)	C25—H25A	0.9900
C9—C12	1.517 (2)	C25—H25B	0.9900
C9—C11	1.519 (2)	C26—H26A	0.9800
C10—H10A	0.9800	C26—H26B	0.9800
C10—H10B	0.9800	C26—H26C	0.9800
C10—H10C	0.9800	O1A—C1A	1.409 (2)
C11—H11A	0.9800	O1A—H1A	0.96 (3)
C11—H11B	0.9800	C1A—H1AA	0.9800
C11—H11C	0.9800	C1A—H1AB	0.9800
C12—H12A	0.9800	C1A—H1AC	0.9800
C12—H12B	0.9800
C8—O1—C9	120.00 (11)	C13—C14—H14B	109.5
C8—N1—C7	122.09 (12)	H14A—C14—H14B	109.5
C8—N1—H1	118.8 (11)	C13—C14—H14C	109.5
C7—N1—H1	119.1 (12)	H14A—C14—H14C	109.5
C16—N2—C15	117.09 (11)	H14B—C14—H14C	109.5
C20—N3—C17	109.34 (11)	N2—C15—C3	111.32 (11)
C20—N3—H3	125.5 (12)	N2—C15—H15A	109.4
C17—N3—H3	125.2 (12)	C3—C15—H15A	109.4
C24—N4—C23	117.16 (11)	N2—C15—H15B	109.4
C2—C1—C6	120.32 (12)	C3—C15—H15B	109.4
C2—C1—C7	120.73 (12)	H15A—C15—H15B	108.0
C6—C1—C7	118.93 (12)	N2—C16—C17	123.50 (12)
C1—C2—C3	119.44 (12)	N2—C16—H16	118.2
C1—C2—C13	120.89 (12)	C17—C16—H16	118.2
C3—C2—C13	119.66 (12)	N3—C17—C18	107.86 (12)
C4—C3—C2	120.41 (12)	N3—C17—C16	124.20 (12)
C4—C3—C15	119.01 (12)	C18—C17—C16	127.81 (13)
C2—C3—C15	120.58 (12)	C17—C18—C19	107.40 (12)
C3—C4—C5	119.60 (12)	C17—C18—H18	126.3
C3—C4—C21	120.68 (12)	C19—C18—H18	126.3
C5—C4—C21	119.72 (12)	C20—C19—C18	107.46 (12)
C6—C5—C4	120.24 (12)	C20—C19—H19	126.3
C6—C5—C23	120.46 (12)	C18—C19—H19	126.3
C4—C5—C23	119.30 (12)	N3—C20—C19	107.93 (12)
C5—C6—C1	119.74 (12)	N3—C20—C24^i	121.63 (12)
C5—C6—C25	120.21 (12)	C19—C20—C24^i	130.17 (12)
C1—C6—C25	120.01 (12)	C4—C21—C22	113.67 (12)
N1—C7—C1	113.67 (12)	C4—C21—H21A	108.8
N1—C7—H7A	108.8	C22—C21—H21A	108.8
C1—C7—H7A	108.8	C4—C21—H21B	108.8
N1—C7—H7B	108.8	C22—C21—H21B	108.8
C1—C7—H7B	108.8	H21A—C21—H21B	107.7
H7A—C7—H7B	107.7	C21—C22—H22A	109.5
O2—C8—O1	125.71 (13)	C21—C22—H22B	109.5
O2—C8—N1	123.99 (13)	H22A—C22—H22B	109.5
O1—C8—N1	110.30 (12)	C21—C22—H22C	109.5
O1—C9—C10	108.95 (11)	H22A—C22—H22C	109.5
O1—C9—C12	102.34 (11)	H22B—C22—H22C	109.5
C10—C9—C12	110.92 (13)	N4—C23—C5	110.74 (11)
O1—C9—C11	111.04 (11)	N4—C23—H23A	109.5
C10—C9—C11	112.58 (12)	C5—C23—H23A	109.5
C12—C9—C11	110.54 (12)	N4—C23—H23B	109.5
C9—C10—H10A	109.5	C5—C23—H23B	109.5
C9—C10—H10B	109.5	H23A—C23—H23B	108.1
H10A—C10—H10B	109.5	N4—C24—C20^i	120.67 (12)
C9—C10—H10C	109.5	N4—C24—H24	119.7
H10A—C10—H10C	109.5	C20^i—C24—H24	119.7
H10B—C10—H10C	109.5	C6—C25—C26	111.82 (11)
C9—C11—H11A	109.5	C6—C25—H25A	109.3
C9—C11—H11B	109.5	C26—C25—H25A	109.3
H11A—C11—H11B	109.5	C6—C25—H25B	109.3
C9—C11—H11C	109.5	C26—C25—H25B	109.3
H11A—C11—H11C	109.5	H25A—C25—H25B	107.9
H11B—C11—H11C	109.5	C25—C26—H26A	109.5
C9—C12—H12A	109.5	C25—C26—H26B	109.5
C9—C12—H12B	109.5	H26A—C26—H26B	109.5
H12A—C12—H12B	109.5	C25—C26—H26C	109.5
C9—C12—H12C	109.5	H26A—C26—H26C	109.5
H12A—C12—H12C	109.5	H26B—C26—H26C	109.5
H12B—C12—H12C	109.5	C1A—O1A—H1A	108.8 (14)
C2—C13—C14	112.48 (12)	O1A—C1A—H1AA	109.5
C2—C13—H13A	109.1	O1A—C1A—H1AB	109.5
C14—C13—H13A	109.1	H1AA—C1A—H1AB	109.5
C2—C13—H13B	109.1	O1A—C1A—H1AC	109.5
C14—C13—H13B	109.1	H1AA—C1A—H1AC	109.5
H13A—C13—H13B	107.8	H1AB—C1A—H1AC	109.5
C13—C14—H14A	109.5
C6—C1—C2—C3	−0.68 (19)	C7—N1—C8—O1	176.84 (12)
C7—C1—C2—C3	177.90 (12)	C8—O1—C9—C10	−67.15 (15)
C6—C1—C2—C13	−179.41 (12)	C8—O1—C9—C12	175.36 (12)
C7—C1—C2—C13	−0.82 (19)	C8—O1—C9—C11	57.39 (16)
C1—C2—C3—C4	4.51 (19)	C1—C2—C13—C14	88.14 (16)
C13—C2—C3—C4	−176.74 (12)	C3—C2—C13—C14	−90.59 (15)
C1—C2—C3—C15	−176.11 (12)	C16—N2—C15—C3	178.58 (12)
C13—C2—C3—C15	2.64 (18)	C4—C3—C15—N2	85.09 (15)
C2—C3—C4—C5	−6.00 (19)	C2—C3—C15—N2	−94.30 (14)
C15—C3—C4—C5	174.61 (12)	C15—N2—C16—C17	176.64 (12)
C2—C3—C4—C21	173.35 (12)	C20—N3—C17—C18	0.28 (15)
C15—C3—C4—C21	−6.04 (18)	C20—N3—C17—C16	−175.81 (12)
C3—C4—C5—C6	3.67 (19)	N2—C16—C17—N3	−8.3 (2)
C21—C4—C5—C6	−175.69 (12)	N2—C16—C17—C18	176.45 (14)
C3—C4—C5—C23	−176.83 (11)	N3—C17—C18—C19	0.42 (15)
C21—C4—C5—C23	3.82 (18)	C16—C17—C18—C19	176.32 (13)
C4—C5—C6—C1	0.12 (19)	C17—C18—C19—C20	−0.95 (16)
C23—C5—C6—C1	−179.38 (12)	C17—N3—C20—C19	−0.87 (15)
C4—C5—C6—C25	−177.44 (12)	C17—N3—C20—C24^i	173.72 (12)
C23—C5—C6—C25	3.06 (19)	C18—C19—C20—N3	1.12 (15)
C2—C1—C6—C5	−1.61 (19)	C18—C19—C20—C24^i	−172.86 (13)
C7—C1—C6—C5	179.77 (12)	C3—C4—C21—C22	92.25 (16)
C2—C1—C6—C25	175.95 (12)	C5—C4—C21—C22	−88.41 (16)
C7—C1—C6—C25	−2.66 (19)	C24—N4—C23—C5	−131.22 (12)
C8—N1—C7—C1	126.91 (14)	C6—C5—C23—N4	93.52 (14)
C2—C1—C7—N1	103.94 (15)	C4—C5—C23—N4	−85.98 (15)
C6—C1—C7—N1	−77.45 (16)	C23—N4—C24—C20^i	179.56 (11)
C9—O1—C8—O2	−4.7 (2)	C5—C6—C25—C26	91.00 (15)
C9—O1—C8—N1	174.71 (11)	C1—C6—C25—C26	−86.55 (15)
C7—N1—C8—O2	−3.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

Cg2 represents the centroid of the C17–C20/N3 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N2	0.96 (3)	1.82 (3)	2.7521 (16)	163 (2)
N3—H3···O1A	0.838 (18)	2.100 (18)	2.8757 (16)	153.6 (16)
C7—H7A···O2	0.99	2.41	2.8234 (17)	104
C10—H10C···O1^ii	0.98	2.63	3.6094 (19)	173
C10—H10B···O2	0.98	2.50	3.0916 (19)	119
C11—H11C···O2	0.98	2.41	2.8986 (18)	110
C18—H18···O2^iii	0.95	2.49	3.3345 (17)	148
C22—H22A···N4^iv	0.98	2.73	3.6080 (18)	149
C24—H24···O2^v	0.95	2.52	3.4120 (17)	157
C25—H25B···O2	0.99	2.48	3.3988 (17)	154
C25—H25B···N1	0.99	2.58	3.3049 (19)	130
C12—H12C···Cg2^vi	0.98	3.00	3.7759 (18)	137
C16—H16···Cg2^vii	0.95	2.88	3.7173 (15)	147

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