Synthesis and structures of three benzoannelated macrobicyclic di­amides

We report the synthesis and structures of 9,10,20,21-tetra­hydro-5,14-(ethano­oxyethano)­dibenzo[e,q][1,4,10,13,7,16]tetra­oxadi­aza­cyclo­octa­decine-6,13-dione [systematic name: 8,11,21,24,29-pentaoxa-1,18-diazatetracyclo[16.8.5.0^2,7.0^12,17]hentriaconta-2,4,6,12(17),13,15-hexaene-19,26-dione C₂₄H₂₈N₂O₈, I], 6,7,9,10,12,13,20,21-octa­hydro-5,14-(ethano­oxyethano)­di­benzo[e,q][1,4,10,13,7,16]tetra­oxadi­aza­cyclo­octa­decine-23,27-dione (8,11,21,24,29-pentaoxa-1,18-diazatetracyclo[16.8.5.0^2,7.0^12,17]hentriaconta-2,4,6,12,14,16-hexaene-27,31-dione; C₂₄H₂₈N₂O₇, II), and 9,10,20,21-tetra­hydro-5,14-(ethano­oxyethano­oxyethano)­dibenzo[e,q][1,4,10,13,7,16]tetra­oxadi­aza­cyclo­octa­decine-6,13-dione [8,11,21,24,29,32-hexa­oxa-1,18-diazatetracyclo[16.8.8.0^2,7.0^12,17]tetratriaconta-2,4,6,12(17),13,15-hexa­ene-19,26-dione; C₂₆H₃₂N₂O₇, III]. All three compounds are made up of two tertiary di­amides and are composed of two 15-membered rings with N₂O₃ donor sets and one 18-membered ring with an N₂O₄ donor set (compounds I and II) or three 18-membered rings with N₂O₄ donor sets (compound III). The solid-state structures of compounds I and II show little effects from the movement of the amide groups. However, compound III has a larger cavity and a different orientation of donor atoms in comparison to compounds I and II.

Computing details

For all structures, data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

8,11,21,24,29,32-Hexaoxa-1,18-diazatetracyclo[16.8.8.0^2,7.0^12,17]tetratriaconta-2,4,6,12(17),13,15-hexaene-19,26-dione (rt3120a)

Crystal data

C26H32N2O8	Z = 2
Mr = 500.53	F(000) = 532
Triclinic, P1	Dx = 1.362 Mg m^−3
a = 8.697 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.203 (4) Å	Cell parameters from 5587 reflections
c = 15.916 (6) Å	θ = 1.4–28.2°
α = 75.369 (8)°	µ = 0.10 mm^−1
β = 82.049 (8)°	T = 100 K
γ = 89.151 (8)°	Plate, colourless
V = 1220.5 (9) Å^3	0.12 × 0.06 × 0.04 mm

Data collection

Bruker APEX CCD diffractometer	4299 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −11→11
Tmin = 0.988, Tmax = 0.996	k = −12→12
10746 measured reflections	l = −21→20
5616 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.155	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.098P)^2 + 0.110P] where P = (Fo^2 + 2Fc^2)/3
5616 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.29 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	0.44101 (15)	0.42638 (13)	0.19048 (8)	0.0203 (3)
O2	0.64296 (14)	0.47120 (13)	0.30973 (9)	0.0203 (3)
O3	0.60115 (14)	0.20985 (14)	0.48549 (8)	0.0195 (3)
O4	0.29340 (15)	0.22733 (14)	0.41911 (8)	0.0206 (3)
O5	0.40223 (15)	−0.08902 (14)	0.25741 (8)	0.0216 (3)
O6	0.61002 (15)	−0.06883 (14)	0.10545 (9)	0.0204 (3)
O7	0.88064 (14)	0.17810 (14)	0.16225 (8)	0.0191 (3)
O8	0.86476 (15)	0.07147 (14)	0.33782 (9)	0.0226 (3)
N1	0.32801 (17)	0.14872 (16)	0.20337 (10)	0.0168 (3)
N2	0.88733 (17)	0.30143 (16)	0.36340 (10)	0.0169 (3)
C1	0.3015 (2)	0.27074 (19)	0.13027 (12)	0.0173 (4)
C2	0.2151 (2)	0.2489 (2)	0.06742 (12)	0.0203 (4)
H2	0.176882	0.151198	0.070669	0.024*
C3	0.1839 (2)	0.3700 (2)	−0.00076 (13)	0.0241 (4)
H3	0.126591	0.354593	−0.044561	0.029*
C4	0.2371 (2)	0.5121 (2)	−0.00385 (13)	0.0260 (4)
H4	0.214218	0.594813	−0.049455	0.031*
C5	0.3237 (2)	0.5359 (2)	0.05873 (13)	0.0236 (4)
H5	0.359980	0.634222	0.055679	0.028*
C6	0.3571 (2)	0.4152 (2)	0.12598 (12)	0.0191 (4)
C7	0.4704 (2)	0.57326 (19)	0.20148 (12)	0.0192 (4)
H7A	0.378859	0.637157	0.191292	0.023*
H7B	0.560673	0.622095	0.159356	0.023*
C8	0.5033 (2)	0.5523 (2)	0.29408 (12)	0.0188 (4)
H8A	0.512668	0.651936	0.306110	0.023*
H8B	0.414872	0.497122	0.335073	0.023*
C9	0.7790 (2)	0.54945 (19)	0.30224 (12)	0.0173 (4)
C10	0.7995 (2)	0.7039 (2)	0.26952 (12)	0.0210 (4)
H10	0.716084	0.763526	0.248478	0.025*
C11	0.9428 (2)	0.7711 (2)	0.26767 (13)	0.0214 (4)
H11	0.955957	0.876920	0.246048	0.026*
C12	1.0667 (2)	0.6854 (2)	0.29704 (13)	0.0220 (4)
H12	1.163794	0.732085	0.296146	0.026*
C13	1.0468 (2)	0.5303 (2)	0.32781 (12)	0.0198 (4)
H13	1.131366	0.471035	0.347533	0.024*
C14	0.9052 (2)	0.46122 (19)	0.33003 (12)	0.0171 (4)
C15	0.8781 (2)	0.2399 (2)	0.45873 (12)	0.0203 (4)
H15A	0.967303	0.279369	0.479382	0.024*
H15B	0.886126	0.129292	0.471632	0.024*
C16	0.7293 (2)	0.2791 (2)	0.50836 (12)	0.0213 (4)
H16A	0.732296	0.243579	0.572231	0.026*
H16B	0.717464	0.389428	0.493655	0.026*
C17	0.4588 (2)	0.2471 (2)	0.52952 (12)	0.0205 (4)
H17A	0.445649	0.357223	0.512292	0.025*
H17B	0.460532	0.216276	0.593635	0.025*
C18	0.3245 (2)	0.1700 (2)	0.50723 (12)	0.0205 (4)
H18A	0.346076	0.061515	0.516833	0.025*
H18B	0.230292	0.180254	0.547854	0.025*
C19	0.3725 (2)	0.1551 (2)	0.35648 (12)	0.0184 (4)
H19A	0.398355	0.050782	0.385144	0.022*
H19B	0.469527	0.210707	0.326406	0.022*
C20	0.2576 (2)	0.1568 (2)	0.29175 (11)	0.0184 (4)
H20A	0.183783	0.070817	0.316469	0.022*
H20B	0.197091	0.249865	0.286280	0.022*
C21	0.3958 (2)	0.01878 (19)	0.19436 (12)	0.0178 (4)
C22	0.4684 (2)	0.0099 (2)	0.10247 (12)	0.0200 (4)
H22A	0.394962	−0.041975	0.076929	0.024*
H22B	0.488160	0.112670	0.064228	0.024*
C23	0.7413 (2)	0.0273 (2)	0.09789 (12)	0.0203 (4)
H23A	0.749495	0.103696	0.041058	0.024*
H23B	0.836467	−0.033081	0.097726	0.024*
C24	0.7333 (2)	0.1066 (2)	0.17133 (12)	0.0195 (4)
H24A	0.650201	0.181795	0.166242	0.023*
H24B	0.711312	0.033313	0.229150	0.023*
C25	0.8817 (2)	0.28347 (19)	0.21289 (12)	0.0183 (4)
H25A	0.791283	0.349453	0.204026	0.022*
H25B	0.977002	0.347178	0.192474	0.022*
C26	0.87562 (19)	0.20771 (19)	0.31107 (12)	0.0173 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0229 (7)	0.0161 (6)	0.0237 (7)	0.0043 (5)	−0.0109 (5)	−0.0043 (5)
O2	0.0136 (6)	0.0157 (6)	0.0327 (7)	0.0045 (5)	−0.0094 (5)	−0.0051 (5)
O3	0.0153 (6)	0.0215 (6)	0.0234 (7)	0.0037 (5)	−0.0047 (5)	−0.0076 (5)
O4	0.0214 (7)	0.0227 (6)	0.0190 (6)	0.0094 (5)	−0.0059 (5)	−0.0063 (5)
O5	0.0241 (7)	0.0164 (6)	0.0234 (7)	0.0035 (5)	−0.0050 (5)	−0.0026 (5)
O6	0.0175 (7)	0.0183 (6)	0.0277 (7)	0.0052 (5)	−0.0067 (5)	−0.0086 (5)
O7	0.0140 (6)	0.0202 (6)	0.0237 (7)	0.0014 (5)	−0.0020 (5)	−0.0070 (5)
O8	0.0239 (7)	0.0164 (6)	0.0266 (7)	0.0030 (5)	−0.0062 (6)	−0.0027 (5)
N1	0.0159 (7)	0.0170 (7)	0.0174 (7)	0.0045 (6)	−0.0046 (6)	−0.0034 (6)
N2	0.0134 (7)	0.0160 (7)	0.0209 (8)	0.0036 (5)	−0.0050 (6)	−0.0029 (6)
C1	0.0145 (8)	0.0177 (8)	0.0184 (8)	0.0060 (6)	−0.0025 (7)	−0.0023 (7)
C2	0.0173 (9)	0.0228 (9)	0.0217 (9)	0.0043 (7)	−0.0041 (7)	−0.0065 (7)
C3	0.0214 (10)	0.0306 (10)	0.0223 (9)	0.0082 (8)	−0.0102 (7)	−0.0073 (8)
C4	0.0268 (10)	0.0265 (10)	0.0225 (9)	0.0084 (8)	−0.0078 (8)	−0.0001 (8)
C5	0.0248 (10)	0.0187 (9)	0.0263 (10)	0.0036 (7)	−0.0079 (8)	−0.0018 (7)
C6	0.0162 (9)	0.0219 (9)	0.0198 (9)	0.0057 (7)	−0.0060 (7)	−0.0047 (7)
C7	0.0164 (9)	0.0144 (8)	0.0268 (9)	0.0040 (6)	−0.0062 (7)	−0.0038 (7)
C8	0.0123 (8)	0.0177 (8)	0.0274 (9)	0.0052 (6)	−0.0052 (7)	−0.0062 (7)
C9	0.0135 (8)	0.0193 (8)	0.0208 (9)	0.0022 (6)	−0.0056 (7)	−0.0068 (7)
C10	0.0200 (9)	0.0176 (9)	0.0258 (10)	0.0056 (7)	−0.0066 (7)	−0.0048 (7)
C11	0.0217 (9)	0.0158 (8)	0.0267 (10)	0.0005 (7)	−0.0038 (7)	−0.0050 (7)
C12	0.0164 (9)	0.0223 (9)	0.0291 (10)	−0.0002 (7)	−0.0050 (7)	−0.0088 (8)
C13	0.0148 (9)	0.0212 (9)	0.0258 (9)	0.0063 (7)	−0.0074 (7)	−0.0080 (7)
C14	0.0160 (9)	0.0167 (8)	0.0199 (9)	0.0042 (6)	−0.0046 (7)	−0.0061 (7)
C15	0.0184 (9)	0.0209 (9)	0.0221 (9)	0.0044 (7)	−0.0090 (7)	−0.0031 (7)
C16	0.0213 (9)	0.0234 (9)	0.0207 (9)	0.0022 (7)	−0.0066 (7)	−0.0064 (7)
C17	0.0197 (9)	0.0207 (9)	0.0221 (9)	0.0066 (7)	−0.0046 (7)	−0.0068 (7)
C18	0.0197 (9)	0.0226 (9)	0.0187 (9)	0.0038 (7)	−0.0033 (7)	−0.0040 (7)
C19	0.0163 (9)	0.0202 (8)	0.0188 (9)	0.0056 (7)	−0.0042 (7)	−0.0048 (7)
C20	0.0154 (8)	0.0200 (9)	0.0191 (9)	0.0042 (7)	−0.0024 (7)	−0.0037 (7)
C21	0.0153 (8)	0.0168 (8)	0.0219 (9)	0.0010 (6)	−0.0047 (7)	−0.0051 (7)
C22	0.0187 (9)	0.0204 (9)	0.0231 (9)	0.0058 (7)	−0.0065 (7)	−0.0079 (7)
C23	0.0164 (9)	0.0208 (9)	0.0241 (9)	0.0019 (7)	−0.0042 (7)	−0.0057 (7)
C24	0.0155 (9)	0.0192 (9)	0.0240 (9)	0.0017 (7)	−0.0037 (7)	−0.0051 (7)
C25	0.0162 (9)	0.0167 (8)	0.0224 (9)	0.0042 (7)	−0.0043 (7)	−0.0049 (7)
C26	0.0088 (8)	0.0190 (8)	0.0234 (9)	0.0036 (6)	−0.0035 (7)	−0.0037 (7)

Geometric parameters (Å, º)

O1—C6	1.364 (2)	C9—C14	1.409 (2)
O1—C7	1.437 (2)	C10—C11	1.392 (3)
O2—C9	1.369 (2)	C10—H10	0.9500
O2—C8	1.434 (2)	C11—C12	1.389 (3)
O3—C17	1.418 (2)	C11—H11	0.9500
O3—C16	1.425 (2)	C12—C13	1.392 (3)
O4—C19	1.429 (2)	C12—H12	0.9500
O4—C18	1.430 (2)	C13—C14	1.387 (3)
O5—C21	1.227 (2)	C13—H13	0.9500
O6—C22	1.420 (2)	C15—C16	1.509 (3)
O6—C23	1.428 (2)	C15—H15A	0.9900
O7—C25	1.410 (2)	C15—H15B	0.9900
O7—C24	1.422 (2)	C16—H16A	0.9900
O8—C26	1.219 (2)	C16—H16B	0.9900
N1—C21	1.357 (2)	C17—C18	1.503 (3)
N1—C1	1.440 (2)	C17—H17A	0.9900
N1—C20	1.474 (2)	C17—H17B	0.9900
N2—C26	1.355 (2)	C18—H18A	0.9900
N2—C14	1.435 (2)	C18—H18B	0.9900
N2—C15	1.471 (2)	C19—C20	1.529 (2)
C1—C2	1.386 (3)	C19—H19A	0.9900
C1—C6	1.403 (3)	C19—H19B	0.9900
C2—C3	1.398 (3)	C20—H20A	0.9900
C2—H2	0.9500	C20—H20B	0.9900
C3—C4	1.381 (3)	C21—C22	1.532 (3)
C3—H3	0.9500	C22—H22A	0.9900
C4—C5	1.389 (3)	C22—H22B	0.9900
C4—H4	0.9500	C23—C24	1.520 (3)
C5—C6	1.393 (2)	C23—H23A	0.9900
C5—H5	0.9500	C23—H23B	0.9900
C7—C8	1.504 (3)	C24—H24A	0.9900
C7—H7A	0.9900	C24—H24B	0.9900
C7—H7B	0.9900	C25—C26	1.536 (2)
C8—H8A	0.9900	C25—H25A	0.9900
C8—H8B	0.9900	C25—H25B	0.9900
C9—C10	1.390 (3)
C6—O1—C7	118.32 (13)	N2—C15—H15B	109.1
C9—O2—C8	119.20 (14)	C16—C15—H15B	109.1
C17—O3—C16	110.95 (14)	H15A—C15—H15B	107.8
C19—O4—C18	115.36 (13)	O3—C16—C15	109.42 (15)
C22—O6—C23	112.73 (14)	O3—C16—H16A	109.8
C25—O7—C24	113.30 (14)	C15—C16—H16A	109.8
C21—N1—C1	123.47 (15)	O3—C16—H16B	109.8
C21—N1—C20	118.06 (14)	C15—C16—H16B	109.8
C1—N1—C20	117.85 (14)	H16A—C16—H16B	108.2
C26—N2—C14	122.69 (15)	O3—C17—C18	110.67 (15)
C26—N2—C15	119.75 (15)	O3—C17—H17A	109.5
C14—N2—C15	117.54 (14)	C18—C17—H17A	109.5
C2—C1—C6	119.94 (16)	O3—C17—H17B	109.5
C2—C1—N1	121.00 (16)	C18—C17—H17B	109.5
C6—C1—N1	118.96 (16)	H17A—C17—H17B	108.1
C1—C2—C3	120.33 (18)	O4—C18—C17	114.05 (15)
C1—C2—H2	119.8	O4—C18—H18A	108.7
C3—C2—H2	119.8	C17—C18—H18A	108.7
C4—C3—C2	119.39 (18)	O4—C18—H18B	108.7
C4—C3—H3	120.3	C17—C18—H18B	108.7
C2—C3—H3	120.3	H18A—C18—H18B	107.6
C3—C4—C5	120.98 (18)	O4—C19—C20	104.50 (14)
C3—C4—H4	119.5	O4—C19—H19A	110.9
C5—C4—H4	119.5	C20—C19—H19A	110.9
C4—C5—C6	119.78 (18)	O4—C19—H19B	110.9
C4—C5—H5	120.1	C20—C19—H19B	110.9
C6—C5—H5	120.1	H19A—C19—H19B	108.9
O1—C6—C5	124.43 (17)	N1—C20—C19	115.15 (15)
O1—C6—C1	116.01 (15)	N1—C20—H20A	108.5
C5—C6—C1	119.56 (17)	C19—C20—H20A	108.5
O1—C7—C8	106.91 (14)	N1—C20—H20B	108.5
O1—C7—H7A	110.3	C19—C20—H20B	108.5
C8—C7—H7A	110.3	H20A—C20—H20B	107.5
O1—C7—H7B	110.3	O5—C21—N1	121.89 (17)
C8—C7—H7B	110.3	O5—C21—C22	119.93 (16)
H7A—C7—H7B	108.6	N1—C21—C22	118.17 (15)
O2—C8—C7	112.33 (15)	O6—C22—C21	111.05 (14)
O2—C8—H8A	109.1	O6—C22—H22A	109.4
C7—C8—H8A	109.1	C21—C22—H22A	109.4
O2—C8—H8B	109.1	O6—C22—H22B	109.4
C7—C8—H8B	109.1	C21—C22—H22B	109.4
H8A—C8—H8B	107.9	H22A—C22—H22B	108.0
O2—C9—C10	125.27 (16)	O6—C23—C24	113.39 (15)
O2—C9—C14	115.06 (15)	O6—C23—H23A	108.9
C10—C9—C14	119.67 (16)	C24—C23—H23A	108.9
C9—C10—C11	119.84 (16)	O6—C23—H23B	108.9
C9—C10—H10	120.1	C24—C23—H23B	108.9
C11—C10—H10	120.1	H23A—C23—H23B	107.7
C12—C11—C10	120.82 (17)	O7—C24—C23	106.43 (15)
C12—C11—H11	119.6	O7—C24—H24A	110.4
C10—C11—H11	119.6	C23—C24—H24A	110.4
C11—C12—C13	119.21 (17)	O7—C24—H24B	110.4
C11—C12—H12	120.4	C23—C24—H24B	110.4
C13—C12—H12	120.4	H24A—C24—H24B	108.6
C14—C13—C12	120.85 (16)	O7—C25—C26	112.23 (14)
C14—C13—H13	119.6	O7—C25—H25A	109.2
C12—C13—H13	119.6	C26—C25—H25A	109.2
C13—C14—C9	119.55 (16)	O7—C25—H25B	109.2
C13—C14—N2	119.63 (15)	C26—C25—H25B	109.2
C9—C14—N2	120.78 (15)	H25A—C25—H25B	107.9
N2—C15—C16	112.61 (14)	O8—C26—N2	123.67 (17)
N2—C15—H15A	109.1	O8—C26—C25	120.61 (16)
C16—C15—H15A	109.1	N2—C26—C25	115.70 (15)
C21—N1—C1—C2	57.2 (2)	C26—N2—C14—C13	−108.1 (2)
C20—N1—C1—C2	−113.65 (19)	C15—N2—C14—C13	73.3 (2)
C21—N1—C1—C6	−126.47 (19)	C26—N2—C14—C9	74.1 (2)
C20—N1—C1—C6	62.7 (2)	C15—N2—C14—C9	−104.50 (19)
C6—C1—C2—C3	0.5 (3)	C26—N2—C15—C16	−109.25 (18)
N1—C1—C2—C3	176.82 (16)	C14—N2—C15—C16	69.4 (2)
C1—C2—C3—C4	−1.4 (3)	C17—O3—C16—C15	−178.67 (14)
C2—C3—C4—C5	1.3 (3)	N2—C15—C16—O3	64.60 (19)
C3—C4—C5—C6	−0.3 (3)	C16—O3—C17—C18	−178.28 (14)
C7—O1—C6—C5	13.4 (3)	C19—O4—C18—C17	90.55 (19)
C7—O1—C6—C1	−166.02 (15)	O3—C17—C18—O4	−70.31 (19)
C4—C5—C6—O1	179.96 (18)	C18—O4—C19—C20	145.18 (15)
C4—C5—C6—C1	−0.6 (3)	C21—N1—C20—C19	68.4 (2)
C2—C1—C6—O1	179.99 (16)	C1—N1—C20—C19	−120.32 (17)
N1—C1—C6—O1	3.6 (2)	O4—C19—C20—N1	155.45 (14)
C2—C1—C6—C5	0.5 (3)	C1—N1—C21—O5	−172.26 (16)
N1—C1—C6—C5	−175.88 (16)	C20—N1—C21—O5	−1.5 (3)
C6—O1—C7—C8	157.37 (15)	C1—N1—C21—C22	8.9 (2)
C9—O2—C8—C7	95.23 (18)	C20—N1—C21—C22	179.71 (15)
O1—C7—C8—O2	65.04 (18)	C23—O6—C22—C21	−88.85 (17)
C8—O2—C9—C10	−8.7 (3)	O5—C21—C22—O6	−38.4 (2)
C8—O2—C9—C14	171.92 (16)	N1—C21—C22—O6	140.45 (16)
O2—C9—C10—C11	178.08 (17)	C22—O6—C23—C24	61.11 (19)
C14—C9—C10—C11	−2.6 (3)	C25—O7—C24—C23	166.72 (14)
C9—C10—C11—C12	0.9 (3)	O6—C23—C24—O7	171.16 (13)
C10—C11—C12—C13	0.6 (3)	C24—O7—C25—C26	73.44 (18)
C11—C12—C13—C14	−0.5 (3)	C14—N2—C26—O8	177.89 (16)
C12—C13—C14—C9	−1.1 (3)	C15—N2—C26—O8	−3.6 (3)
C12—C13—C14—N2	−178.99 (17)	C14—N2—C26—C25	−0.3 (2)
O2—C9—C14—C13	−177.90 (16)	C15—N2—C26—C25	178.21 (14)
C10—C9—C14—C13	2.7 (3)	O7—C25—C26—O8	−2.8 (2)
O2—C9—C14—N2	−0.1 (3)	O7—C25—C26—N2	175.51 (14)
C10—C9—C14—N2	−179.50 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O5^i	0.99	2.53	3.331 (3)	138
C18—H18A···O3^ii	0.99	2.54	3.521 (3)	171
C18—H18B···O8^ii	0.99	2.62	3.154 (2)	114
C19—H19B···O1	0.99	2.58	3.138 (2)	116
C24—H24B···O8	0.99	2.42	2.971 (2)	115
C25—H25A···O2	0.99	2.46	3.166 (2)	128

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

8,11,21,24,29-Pentaoxa-1,18-diazatetracyclo[16.8.5.0^2,7.0^12,17]hentriaconta-2,4,6,12(17),13,15-hexaene-19,26-dione (rt3163a)

Crystal data

C24H28N2O7	Dx = 1.396 Mg m^−3
Mr = 456.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7823 reflections
a = 16.208 (8) Å	θ = 3.2–25.9°
b = 14.849 (8) Å	µ = 0.10 mm^−1
c = 18.052 (9) Å	T = 120 K
V = 4345 (4) Å^3	Plate, colourless
Z = 8	0.42 × 0.32 × 0.22 mm
F(000) = 1936

Data collection

Bruker APEX CCD diffractometer	3301 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.092
ω scans	θmax = 26.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −20→20
Tmin = 0.958, Tmax = 0.978	k = −18→18
41308 measured reflections	l = −22→21
4493 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.072P)^2 + 4.P] where P = (Fo^2 + 2Fc^2)/3
4493 reflections	(Δ/σ)max < 0.001
298 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.31 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	0.59734 (10)	0.14661 (10)	0.52064 (9)	0.0300 (4)
O2	0.68974 (10)	0.24739 (10)	0.41719 (9)	0.0300 (4)
O3	0.48250 (10)	0.32310 (10)	0.43584 (9)	0.0290 (4)
O4	0.40937 (11)	0.35551 (11)	0.59310 (10)	0.0370 (4)
O5	0.55974 (11)	0.35669 (11)	0.67702 (9)	0.0343 (4)
O6	0.66100 (11)	0.48417 (10)	0.59017 (9)	0.0322 (4)
O7	0.75159 (10)	0.42897 (11)	0.47179 (10)	0.0324 (4)
N1	0.64358 (11)	0.42007 (12)	0.39394 (11)	0.0263 (4)
N2	0.44825 (12)	0.21187 (12)	0.56880 (11)	0.0270 (4)
C1	0.48106 (14)	0.12798 (14)	0.59655 (13)	0.0270 (5)
C2	0.43506 (15)	0.07987 (15)	0.64794 (14)	0.0313 (5)
H2	0.381281	0.099889	0.660852	0.038*
C3	0.46693 (17)	0.00284 (16)	0.68060 (14)	0.0347 (6)
H3	0.435521	−0.030374	0.715642	0.042*
C4	0.54566 (16)	−0.02454 (16)	0.66092 (14)	0.0345 (6)
H4	0.569079	−0.075633	0.684612	0.041*
C5	0.59099 (15)	0.02051 (15)	0.60777 (14)	0.0316 (5)
H5	0.644018	−0.000923	0.593913	0.038*
C6	0.55862 (14)	0.09758 (15)	0.57452 (12)	0.0270 (5)
C7	0.68282 (15)	0.12892 (17)	0.50594 (15)	0.0351 (6)
H7A	0.694923	0.064425	0.514601	0.042*
H7B	0.717753	0.165033	0.539730	0.042*
C8	0.70169 (15)	0.15283 (15)	0.42737 (14)	0.0318 (5)
H8A	0.759471	0.136607	0.415597	0.038*
H8B	0.664918	0.118874	0.393640	0.038*
C9	0.71523 (14)	0.28412 (15)	0.35207 (13)	0.0269 (5)
C10	0.76051 (14)	0.23893 (17)	0.29805 (14)	0.0317 (5)
H10	0.775253	0.177590	0.304995	0.038*
C11	0.78401 (15)	0.28386 (17)	0.23408 (14)	0.0346 (6)
H11	0.815027	0.252630	0.197555	0.042*
C12	0.76332 (15)	0.37307 (17)	0.22222 (14)	0.0341 (6)
H12	0.780227	0.403104	0.178311	0.041*
C13	0.71738 (15)	0.41795 (16)	0.27565 (14)	0.0318 (5)
H13	0.702103	0.478982	0.267831	0.038*
C14	0.69356 (13)	0.37469 (15)	0.34031 (13)	0.0263 (5)
C15	0.55776 (14)	0.43895 (15)	0.37225 (13)	0.0281 (5)
H15A	0.557811	0.471439	0.324364	0.034*
H15B	0.532437	0.478990	0.409749	0.034*
C16	0.50577 (15)	0.35527 (16)	0.36481 (13)	0.0301 (5)
H16A	0.455747	0.369002	0.335429	0.036*
H16B	0.537407	0.308171	0.338351	0.036*
C17	0.45148 (15)	0.23366 (15)	0.43144 (13)	0.0300 (5)
H17A	0.498078	0.190877	0.427108	0.036*
H17B	0.416698	0.227453	0.386646	0.036*
C18	0.40104 (14)	0.21099 (16)	0.49936 (14)	0.0313 (5)
H18A	0.355179	0.254744	0.503491	0.038*
H18B	0.376483	0.150482	0.492704	0.038*
C19	0.44715 (14)	0.28741 (15)	0.61114 (14)	0.0301 (5)
C21	0.62457 (15)	0.32864 (15)	0.62889 (13)	0.0308 (5)
H21A	0.601963	0.315376	0.579120	0.037*
H21B	0.650369	0.273043	0.648374	0.037*
C22	0.68812 (16)	0.40201 (16)	0.62342 (14)	0.0340 (6)
H22A	0.708332	0.415622	0.673947	0.041*
H22B	0.735516	0.378825	0.594551	0.041*
C23	0.62090 (14)	0.47566 (15)	0.52087 (13)	0.0284 (5)
H23A	0.599441	0.535263	0.505624	0.034*
H23B	0.573286	0.434406	0.526210	0.034*
C24	0.67813 (14)	0.43976 (14)	0.46050 (13)	0.0264 (5)
C20	0.49809 (17)	0.28888 (16)	0.68228 (14)	0.0348 (6)
H20A	0.461733	0.301339	0.725144	0.042*
H20B	0.524383	0.229441	0.689997	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0336 (8)	0.0257 (8)	0.0306 (9)	0.0038 (6)	0.0051 (7)	0.0063 (7)
O2	0.0435 (9)	0.0202 (8)	0.0264 (9)	0.0017 (6)	0.0064 (7)	0.0012 (6)
O3	0.0398 (9)	0.0229 (8)	0.0242 (8)	−0.0031 (6)	0.0013 (7)	−0.0006 (6)
O4	0.0449 (10)	0.0220 (8)	0.0441 (11)	0.0045 (7)	0.0053 (8)	0.0046 (7)
O5	0.0473 (10)	0.0249 (8)	0.0306 (9)	−0.0034 (7)	0.0034 (8)	−0.0045 (7)
O6	0.0476 (10)	0.0230 (8)	0.0260 (9)	−0.0018 (7)	−0.0057 (7)	−0.0025 (7)
O7	0.0312 (8)	0.0315 (9)	0.0345 (9)	0.0008 (7)	−0.0031 (7)	−0.0044 (7)
N1	0.0314 (10)	0.0229 (9)	0.0245 (10)	0.0019 (7)	0.0017 (8)	0.0003 (8)
N2	0.0321 (10)	0.0205 (9)	0.0283 (10)	0.0008 (7)	0.0018 (8)	0.0028 (8)
C1	0.0373 (12)	0.0194 (10)	0.0242 (12)	−0.0017 (9)	−0.0001 (9)	−0.0010 (9)
C2	0.0378 (13)	0.0273 (12)	0.0288 (12)	−0.0033 (9)	0.0039 (10)	−0.0017 (10)
C3	0.0517 (15)	0.0269 (11)	0.0254 (12)	−0.0085 (10)	0.0023 (11)	0.0031 (10)
C4	0.0525 (15)	0.0218 (11)	0.0293 (13)	−0.0005 (10)	−0.0035 (11)	0.0039 (10)
C5	0.0419 (13)	0.0233 (11)	0.0296 (13)	0.0025 (9)	0.0015 (11)	0.0004 (10)
C6	0.0369 (12)	0.0206 (10)	0.0234 (11)	−0.0029 (9)	0.0003 (9)	0.0001 (9)
C7	0.0347 (12)	0.0307 (13)	0.0400 (15)	0.0055 (10)	0.0054 (11)	0.0075 (11)
C8	0.0378 (12)	0.0206 (11)	0.0370 (14)	0.0008 (9)	0.0078 (11)	0.0010 (10)
C9	0.0297 (11)	0.0270 (11)	0.0241 (12)	−0.0035 (9)	0.0024 (9)	0.0011 (9)
C10	0.0336 (12)	0.0309 (12)	0.0306 (13)	−0.0001 (9)	0.0016 (10)	−0.0057 (10)
C11	0.0362 (12)	0.0422 (14)	0.0255 (13)	−0.0031 (10)	0.0055 (10)	−0.0085 (11)
C12	0.0364 (13)	0.0412 (14)	0.0248 (12)	−0.0052 (10)	0.0018 (10)	0.0018 (10)
C13	0.0360 (12)	0.0304 (12)	0.0289 (13)	−0.0022 (9)	−0.0021 (10)	0.0048 (10)
C14	0.0284 (11)	0.0243 (11)	0.0260 (12)	−0.0013 (8)	0.0008 (9)	−0.0023 (9)
C15	0.0342 (12)	0.0259 (11)	0.0241 (12)	0.0023 (9)	0.0005 (9)	0.0034 (9)
C16	0.0347 (12)	0.0329 (12)	0.0227 (12)	0.0006 (10)	0.0002 (10)	0.0009 (10)
C17	0.0371 (12)	0.0237 (11)	0.0293 (13)	−0.0023 (9)	−0.0081 (10)	−0.0012 (9)
C18	0.0315 (12)	0.0275 (11)	0.0350 (13)	−0.0030 (9)	−0.0051 (10)	0.0028 (10)
C19	0.0358 (12)	0.0221 (11)	0.0324 (13)	−0.0014 (9)	0.0087 (10)	0.0029 (9)
C21	0.0402 (13)	0.0257 (11)	0.0263 (12)	0.0021 (9)	−0.0028 (10)	−0.0008 (9)
C22	0.0412 (13)	0.0305 (12)	0.0304 (13)	−0.0006 (10)	−0.0076 (11)	0.0021 (10)
C23	0.0371 (12)	0.0224 (11)	0.0257 (12)	0.0018 (9)	−0.0044 (10)	0.0002 (9)
C24	0.0352 (12)	0.0177 (10)	0.0264 (12)	−0.0026 (8)	−0.0015 (10)	0.0010 (9)
C20	0.0517 (15)	0.0241 (11)	0.0285 (13)	−0.0015 (10)	0.0076 (11)	−0.0012 (10)

Geometric parameters (Å, º)

O1—C6	1.367 (3)	C8—H8B	0.9900
O1—C7	1.435 (3)	C9—C10	1.393 (3)
O2—C9	1.360 (3)	C9—C14	1.406 (3)
O2—C8	1.429 (3)	C10—C11	1.387 (4)
O3—C16	1.419 (3)	C10—H10	0.9500
O3—C17	1.422 (3)	C11—C12	1.383 (4)
O4—C19	1.226 (3)	C11—H11	0.9500
O5—C20	1.422 (3)	C12—C13	1.389 (4)
O5—C21	1.426 (3)	C12—H12	0.9500
O6—C23	1.415 (3)	C13—C14	1.387 (3)
O6—C22	1.429 (3)	C13—H13	0.9500
O7—C24	1.219 (3)	C15—C16	1.507 (3)
N1—C24	1.358 (3)	C15—H15A	0.9900
N1—C14	1.431 (3)	C15—H15B	0.9900
N1—C15	1.472 (3)	C16—H16A	0.9900
N2—C19	1.358 (3)	C16—H16B	0.9900
N2—C1	1.444 (3)	C17—C18	1.512 (3)
N2—C18	1.469 (3)	C17—H17A	0.9900
C1—C2	1.388 (3)	C17—H17B	0.9900
C1—C6	1.394 (3)	C18—H18A	0.9900
C2—C3	1.387 (3)	C18—H18B	0.9900
C2—H2	0.9500	C19—C20	1.527 (4)
C3—C4	1.386 (4)	C21—C22	1.503 (3)
C3—H3	0.9500	C21—H21A	0.9900
C4—C5	1.381 (3)	C21—H21B	0.9900
C4—H4	0.9500	C22—H22A	0.9900
C5—C6	1.395 (3)	C22—H22B	0.9900
C5—H5	0.9500	C23—C24	1.527 (3)
C7—C8	1.494 (4)	C23—H23A	0.9900
C7—H7A	0.9900	C23—H23B	0.9900
C7—H7B	0.9900	C20—H20A	0.9900
C8—H8A	0.9900	C20—H20B	0.9900
C6—O1—C7	118.50 (18)	C13—C14—N1	120.6 (2)
C9—O2—C8	117.64 (18)	C9—C14—N1	119.3 (2)
C16—O3—C17	110.95 (17)	N1—C15—C16	113.27 (18)
C20—O5—C21	110.60 (17)	N1—C15—H15A	108.9
C23—O6—C22	115.86 (17)	C16—C15—H15A	108.9
C24—N1—C14	117.82 (19)	N1—C15—H15B	108.9
C24—N1—C15	125.75 (19)	C16—C15—H15B	108.9
C14—N1—C15	116.41 (19)	H15A—C15—H15B	107.7
C19—N2—C1	121.5 (2)	O3—C16—C15	110.20 (19)
C19—N2—C18	118.76 (19)	O3—C16—H16A	109.6
C1—N2—C18	118.71 (18)	C15—C16—H16A	109.6
C2—C1—C6	120.6 (2)	O3—C16—H16B	109.6
C2—C1—N2	118.6 (2)	C15—C16—H16B	109.6
C6—C1—N2	120.8 (2)	H16A—C16—H16B	108.1
C3—C2—C1	120.6 (2)	O3—C17—C18	110.72 (19)
C3—C2—H2	119.7	O3—C17—H17A	109.5
C1—C2—H2	119.7	C18—C17—H17A	109.5
C4—C3—C2	118.4 (2)	O3—C17—H17B	109.5
C4—C3—H3	120.8	C18—C17—H17B	109.5
C2—C3—H3	120.8	H17A—C17—H17B	108.1
C5—C4—C3	121.7 (2)	N2—C18—C17	114.11 (19)
C5—C4—H4	119.1	N2—C18—H18A	108.7
C3—C4—H4	119.1	C17—C18—H18A	108.7
C4—C5—C6	119.8 (2)	N2—C18—H18B	108.7
C4—C5—H5	120.1	C17—C18—H18B	108.7
C6—C5—H5	120.1	H18A—C18—H18B	107.6
O1—C6—C1	116.4 (2)	O4—C19—N2	122.6 (2)
O1—C6—C5	124.8 (2)	O4—C19—C20	118.8 (2)
C1—C6—C5	118.8 (2)	N2—C19—C20	118.6 (2)
O1—C7—C8	109.3 (2)	O5—C21—C22	109.48 (19)
O1—C7—H7A	109.8	O5—C21—H21A	109.8
C8—C7—H7A	109.8	C22—C21—H21A	109.8
O1—C7—H7B	109.8	O5—C21—H21B	109.8
C8—C7—H7B	109.8	C22—C21—H21B	109.8
H7A—C7—H7B	108.3	H21A—C21—H21B	108.2
O2—C8—C7	109.13 (19)	O6—C22—C21	115.8 (2)
O2—C8—H8A	109.9	O6—C22—H22A	108.3
C7—C8—H8A	109.9	C21—C22—H22A	108.3
O2—C8—H8B	109.9	O6—C22—H22B	108.3
C7—C8—H8B	109.9	C21—C22—H22B	108.3
H8A—C8—H8B	108.3	H22A—C22—H22B	107.4
O2—C9—C10	124.9 (2)	O6—C23—C24	112.52 (19)
O2—C9—C14	116.0 (2)	O6—C23—H23A	109.1
C10—C9—C14	119.1 (2)	C24—C23—H23A	109.1
C11—C10—C9	119.7 (2)	O6—C23—H23B	109.1
C11—C10—H10	120.1	C24—C23—H23B	109.1
C9—C10—H10	120.1	H23A—C23—H23B	107.8
C12—C11—C10	121.5 (2)	O7—C24—N1	121.5 (2)
C12—C11—H11	119.2	O7—C24—C23	121.3 (2)
C10—C11—H11	119.2	N1—C24—C23	117.1 (2)
C11—C12—C13	118.8 (2)	O5—C20—C19	109.51 (19)
C11—C12—H12	120.6	O5—C20—H20A	109.8
C13—C12—H12	120.6	C19—C20—H20A	109.8
C14—C13—C12	120.7 (2)	O5—C20—H20B	109.8
C14—C13—H13	119.6	C19—C20—H20B	109.8
C12—C13—H13	119.6	H20A—C20—H20B	108.2
C13—C14—C9	120.0 (2)
C19—N2—C1—C2	73.9 (3)	O2—C9—C14—N1	−3.4 (3)
C18—N2—C1—C2	−94.2 (3)	C10—C9—C14—N1	176.9 (2)
C19—N2—C1—C6	−103.6 (3)	C24—N1—C14—C13	−112.6 (2)
C18—N2—C1—C6	88.3 (3)	C15—N1—C14—C13	69.1 (3)
C6—C1—C2—C3	2.8 (4)	C24—N1—C14—C9	70.4 (3)
N2—C1—C2—C3	−174.8 (2)	C15—N1—C14—C9	−107.9 (2)
C1—C2—C3—C4	0.3 (4)	C24—N1—C15—C16	−110.1 (2)
C2—C3—C4—C5	−2.8 (4)	C14—N1—C15—C16	68.0 (3)
C3—C4—C5—C6	2.4 (4)	C17—O3—C16—C15	−165.59 (18)
C7—O1—C6—C1	168.3 (2)	N1—C15—C16—O3	77.3 (2)
C7—O1—C6—C5	−12.0 (3)	C16—O3—C17—C18	−160.80 (19)
C2—C1—C6—O1	176.4 (2)	C19—N2—C18—C17	96.0 (2)
N2—C1—C6—O1	−6.1 (3)	C1—N2—C18—C17	−95.6 (2)
C2—C1—C6—C5	−3.2 (3)	O3—C17—C18—N2	−63.2 (2)
N2—C1—C6—C5	174.2 (2)	C1—N2—C19—O4	−169.3 (2)
C4—C5—C6—O1	−178.9 (2)	C18—N2—C19—O4	−1.2 (3)
C4—C5—C6—C1	0.7 (3)	C1—N2—C19—C20	13.4 (3)
C6—O1—C7—C8	152.89 (19)	C18—N2—C19—C20	−178.45 (19)
C9—O2—C8—C7	170.75 (19)	C20—O5—C21—C22	179.14 (19)
O1—C7—C8—O2	63.7 (3)	C23—O6—C22—C21	−50.8 (3)
C8—O2—C9—C10	−7.8 (3)	O5—C21—C22—O6	−64.5 (3)
C8—O2—C9—C14	172.6 (2)	C22—O6—C23—C24	−64.9 (2)
O2—C9—C10—C11	−179.2 (2)	C14—N1—C24—O7	8.3 (3)
C14—C9—C10—C11	0.5 (3)	C15—N1—C24—O7	−173.5 (2)
C9—C10—C11—C12	−0.2 (4)	C14—N1—C24—C23	−171.37 (18)
C10—C11—C12—C13	−0.5 (4)	C15—N1—C24—C23	6.7 (3)
C11—C12—C13—C14	0.9 (4)	O6—C23—C24—O7	−6.5 (3)
C12—C13—C14—C9	−0.6 (4)	O6—C23—C24—N1	173.20 (18)
C12—C13—C14—N1	−177.6 (2)	C21—O5—C20—C19	−74.5 (2)
O2—C9—C14—C13	179.6 (2)	O4—C19—C20—O5	−60.1 (3)
C10—C9—C14—C13	−0.1 (3)	N2—C19—C20—O5	117.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O7^i	0.99	2.32	3.213 (3)	149
C8—H8A···O4^ii	0.99	2.44	3.389 (3)	161
C15—H15B···O4^iii	0.99	2.63	3.161 (3)	114
C17—H17A···O1	0.99	2.42	3.139 (3)	129
C18—H18B···O7^iv	0.99	2.43	3.234 (3)	138
C22—H22B···O7	0.99	2.35	2.951 (3)	118
C23—H23A···O4^iii	0.99	2.41	3.280 (3)	146

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x−1/2, −y+1/2, −z+1.

8,11,21,24,29-pentaoxa-1,18-diazatetracyclo[16.8.5.0^2,7.0^12,17]hentriaconta-2,4,6,12,14,16-hexaene-27,31-dione (rt4048a)

Crystal data

C24H28N2O7	F(000) = 968
Mr = 456.48	Dx = 1.371 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.6238 (7) Å	Cell parameters from 7345 reflections
b = 23.318 (2) Å	θ = 3.2–26.4°
c = 12.6550 (12) Å	µ = 0.10 mm^−1
β = 100.6770 (14)°	T = 100 K
V = 2210.8 (3) Å^3	Block, colourless
Z = 4	0.30 × 0.22 × 0.16 mm

Data collection

Bruker APEX CCD diffractometer	9276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.970, Tmax = 0.984	k = −30→30
26492 measured reflections	l = −16→16
10031 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.4P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
10031 reflections	Δρmax = 0.26 e Å^−3
595 parameters	Δρmin = −0.20 e Å^−3
1 restraint	Absolute structure: Flack x determined using 4079 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (2)

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	1.0467 (2)	0.70914 (7)	0.56596 (13)	0.0192 (4)
O2	0.9632 (2)	0.74135 (7)	0.76497 (13)	0.0180 (3)
O3	0.9192 (2)	0.93097 (7)	0.59815 (15)	0.0239 (4)
O4	1.0924 (2)	0.84220 (7)	0.46310 (14)	0.0214 (4)
O5	0.6319 (2)	0.81555 (8)	0.40074 (15)	0.0238 (4)
O6	0.4588 (2)	0.74674 (8)	0.52483 (14)	0.0218 (4)
O7	0.5620 (2)	0.74078 (8)	0.74883 (14)	0.0216 (4)
N1	0.8343 (3)	0.74777 (9)	0.37970 (15)	0.0176 (4)
N2	0.7034 (3)	0.82564 (9)	0.74816 (16)	0.0175 (4)
C1	0.9021 (3)	0.68998 (10)	0.3891 (2)	0.0187 (5)
C2	0.8633 (3)	0.65364 (11)	0.3012 (2)	0.0217 (5)
H2A	0.782488	0.665803	0.238892	0.026*
C3	0.9410 (4)	0.59959 (11)	0.3030 (2)	0.0245 (5)
H3A	0.912322	0.574761	0.242799	0.029*
C4	1.0609 (4)	0.58229 (11)	0.3939 (2)	0.0236 (5)
H4A	1.117116	0.545890	0.394802	0.028*
C5	1.0992 (3)	0.61762 (11)	0.4830 (2)	0.0208 (5)
H5A	1.179995	0.605033	0.545072	0.025*
C6	1.0196 (3)	0.67192 (10)	0.48248 (19)	0.0182 (5)
C7	1.1487 (3)	0.68882 (11)	0.66645 (19)	0.0183 (5)
H7A	1.273338	0.681043	0.658624	0.022*
H7B	1.096366	0.652800	0.688043	0.022*
C8	1.1452 (3)	0.73402 (10)	0.74978 (19)	0.0181 (5)
H8A	1.221931	0.722443	0.818362	0.022*
H8B	1.191315	0.770627	0.726174	0.022*
C9	0.9440 (3)	0.76965 (10)	0.85723 (19)	0.0166 (5)
C10	1.0456 (3)	0.75635 (10)	0.95758 (19)	0.0176 (5)
H10A	1.133433	0.727019	0.963895	0.021*
C11	1.0184 (3)	0.78598 (10)	1.04812 (19)	0.0184 (5)
H11A	1.088237	0.776752	1.116203	0.022*
C12	0.8900 (3)	0.82912 (11)	1.0409 (2)	0.0195 (5)
H12A	0.873072	0.849539	1.103158	0.023*
C13	0.7877 (3)	0.84169 (10)	0.9415 (2)	0.0182 (5)
H13A	0.699614	0.870911	0.935585	0.022*
C14	0.8124 (3)	0.81205 (10)	0.85032 (19)	0.0170 (5)
C15	0.7397 (3)	0.88083 (10)	0.7001 (2)	0.0201 (5)
H15A	0.768032	0.910119	0.757369	0.024*
H15B	0.631933	0.893570	0.649390	0.024*
C16	0.8948 (3)	0.87558 (11)	0.6409 (2)	0.0203 (5)
H16A	1.004103	0.863344	0.690792	0.024*
H16B	0.867407	0.847024	0.582270	0.024*
C17	1.0638 (4)	0.93428 (11)	0.5412 (2)	0.0260 (6)
H17A	1.173704	0.920747	0.589022	0.031*
H17B	1.082357	0.974981	0.523851	0.031*
C18	1.0380 (4)	0.89996 (11)	0.4383 (2)	0.0253 (6)
H18A	0.910940	0.900871	0.402820	0.030*
H18B	1.110051	0.916745	0.388528	0.030*
C19	1.1014 (3)	0.80726 (11)	0.3724 (2)	0.0211 (5)
H19A	1.176759	0.773412	0.396269	0.025*
H19B	1.159982	0.829208	0.321652	0.025*
C20	0.9198 (3)	0.78676 (11)	0.31341 (19)	0.0204 (5)
H20A	0.841539	0.820354	0.292911	0.025*
H20B	0.934674	0.766766	0.246608	0.025*
C21	0.6945 (3)	0.76770 (11)	0.42196 (19)	0.0187 (5)
C22	0.6222 (3)	0.72766 (11)	0.4992 (2)	0.0211 (5)
H22A	0.604566	0.689051	0.466394	0.025*
H22B	0.711816	0.724250	0.566326	0.025*
C23	0.4767 (3)	0.79713 (11)	0.5898 (2)	0.0221 (5)
H23A	0.356802	0.811382	0.596194	0.027*
H23B	0.537017	0.827396	0.554890	0.027*
C24	0.5844 (3)	0.78504 (10)	0.70187 (19)	0.0183 (5)
O8	0.3760 (2)	1.06054 (7)	0.21512 (13)	0.0189 (4)
O9	0.4849 (2)	1.13290 (7)	0.06159 (14)	0.0209 (4)
O10	0.4675 (3)	0.95660 (8)	−0.14362 (15)	0.0265 (4)
O11	0.2807 (2)	0.94715 (7)	0.05527 (14)	0.0223 (4)
O12	0.7357 (3)	0.92828 (8)	0.15803 (17)	0.0287 (4)
O13	0.9491 (2)	1.02252 (8)	0.19929 (14)	0.0209 (4)
O14	0.8659 (2)	1.12678 (7)	0.10206 (14)	0.0204 (4)
N3	0.5443 (3)	0.95659 (9)	0.26409 (16)	0.0181 (4)
N4	0.7236 (3)	1.08640 (9)	−0.05243 (17)	0.0192 (4)
C25	0.4977 (3)	0.99303 (10)	0.3464 (2)	0.0186 (5)
C26	0.5354 (3)	0.97450 (11)	0.4525 (2)	0.0224 (5)
H26A	0.597774	0.939473	0.469690	0.027*
C27	0.4831 (4)	1.00646 (12)	0.5338 (2)	0.0255 (5)
H27A	0.511070	0.993857	0.606332	0.031*
C28	0.3896 (4)	1.05694 (12)	0.5078 (2)	0.0247 (5)
H28A	0.351204	1.078561	0.562941	0.030*
C29	0.3510 (3)	1.07648 (11)	0.4025 (2)	0.0228 (5)
H29A	0.287822	1.111433	0.386165	0.027*
C30	0.4051 (3)	1.04481 (10)	0.32035 (19)	0.0175 (5)
C31	0.2994 (3)	1.11669 (10)	0.1914 (2)	0.0193 (5)
H31A	0.369600	1.145735	0.238356	0.023*
H31B	0.175319	1.117393	0.204444	0.023*
C32	0.3016 (3)	1.12985 (11)	0.0758 (2)	0.0219 (5)
H32A	0.237731	1.099475	0.029231	0.026*
H32B	0.240915	1.166855	0.055600	0.026*
C33	0.5171 (3)	1.16340 (10)	−0.02533 (19)	0.0185 (5)
C34	0.4433 (3)	1.21743 (11)	−0.0529 (2)	0.0222 (5)
H34A	0.366653	1.234651	−0.010776	0.027*
C35	0.4826 (3)	1.24583 (12)	−0.1420 (2)	0.0259 (6)
H35A	0.432266	1.282568	−0.160519	0.031*
C36	0.5941 (3)	1.22141 (12)	−0.2045 (2)	0.0262 (6)
H36A	0.615862	1.240465	−0.267219	0.031*
C37	0.6736 (3)	1.16899 (12)	−0.1748 (2)	0.0236 (5)
H37A	0.753687	1.152719	−0.215765	0.028*
C38	0.6368 (3)	1.13998 (10)	−0.08521 (19)	0.0182 (5)
C39	0.6639 (4)	1.03563 (11)	−0.1184 (2)	0.0223 (5)
H39A	0.761438	1.007022	−0.109747	0.027*
H39B	0.635489	1.046841	−0.195105	0.027*
C40	0.5003 (4)	1.00895 (11)	−0.0859 (2)	0.0229 (5)
H40A	0.522073	1.001650	−0.007527	0.027*
H40B	0.396356	1.034923	−0.104292	0.027*
C41	0.3080 (4)	0.92802 (13)	−0.1284 (2)	0.0300 (6)
H41A	0.282705	0.896541	−0.181514	0.036*
H41B	0.207578	0.955536	−0.143793	0.036*
C42	0.3134 (4)	0.90330 (12)	−0.0173 (2)	0.0284 (6)
H42A	0.221895	0.872890	−0.020673	0.034*
H42B	0.431778	0.885846	0.008997	0.034*
C43	0.2544 (3)	0.92539 (11)	0.1568 (2)	0.0210 (5)
H43A	0.173565	0.891848	0.144181	0.025*
H43B	0.194590	0.955192	0.193181	0.025*
C44	0.4261 (3)	0.90754 (10)	0.2311 (2)	0.0205 (5)
H44A	0.396363	0.888932	0.295889	0.025*
H44B	0.489468	0.879098	0.193874	0.025*
C45	0.6901 (3)	0.96398 (10)	0.2189 (2)	0.0196 (5)
C46	0.7941 (3)	1.01977 (11)	0.2457 (2)	0.0208 (5)
H46A	0.715554	1.052581	0.219542	0.025*
H46B	0.829077	1.023321	0.324746	0.025*
C47	0.9109 (3)	1.02589 (11)	0.0848 (2)	0.0213 (5)
H47A	0.826187	0.995060	0.055897	0.026*
H47B	1.022286	1.019883	0.056566	0.026*
C48	0.8305 (3)	1.08407 (10)	0.0466 (2)	0.0185 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0228 (9)	0.0185 (8)	0.0158 (8)	0.0043 (7)	0.0028 (7)	0.0013 (7)
O2	0.0162 (8)	0.0209 (8)	0.0172 (8)	0.0027 (7)	0.0034 (6)	−0.0036 (7)
O3	0.0268 (9)	0.0164 (9)	0.0306 (10)	0.0009 (7)	0.0108 (8)	0.0050 (7)
O4	0.0222 (9)	0.0200 (9)	0.0214 (9)	0.0020 (7)	0.0021 (7)	0.0020 (7)
O5	0.0266 (9)	0.0208 (9)	0.0245 (9)	0.0049 (7)	0.0058 (7)	0.0051 (7)
O6	0.0161 (8)	0.0256 (9)	0.0241 (9)	−0.0002 (7)	0.0046 (7)	−0.0020 (8)
O7	0.0198 (8)	0.0188 (9)	0.0259 (9)	−0.0007 (7)	0.0031 (7)	0.0038 (7)
N1	0.0193 (10)	0.0177 (10)	0.0159 (9)	0.0020 (8)	0.0033 (8)	0.0032 (8)
N2	0.0178 (9)	0.0166 (10)	0.0180 (10)	0.0032 (8)	0.0028 (8)	0.0036 (8)
C1	0.0181 (11)	0.0179 (11)	0.0210 (12)	0.0019 (9)	0.0064 (9)	0.0016 (10)
C2	0.0200 (12)	0.0263 (13)	0.0186 (12)	0.0015 (10)	0.0030 (9)	−0.0002 (10)
C3	0.0272 (13)	0.0237 (13)	0.0229 (13)	−0.0009 (10)	0.0058 (10)	−0.0077 (10)
C4	0.0252 (13)	0.0183 (12)	0.0296 (14)	0.0035 (10)	0.0111 (11)	−0.0006 (10)
C5	0.0207 (12)	0.0212 (12)	0.0211 (12)	0.0029 (10)	0.0057 (10)	0.0045 (10)
C6	0.0186 (11)	0.0191 (12)	0.0185 (11)	−0.0005 (9)	0.0073 (9)	0.0015 (9)
C7	0.0180 (11)	0.0204 (12)	0.0167 (11)	0.0044 (9)	0.0038 (9)	0.0019 (10)
C8	0.0159 (11)	0.0200 (12)	0.0185 (11)	0.0024 (9)	0.0037 (9)	0.0002 (9)
C9	0.0164 (11)	0.0150 (11)	0.0183 (11)	−0.0009 (9)	0.0034 (9)	−0.0001 (9)
C10	0.0166 (11)	0.0159 (12)	0.0204 (12)	0.0016 (9)	0.0039 (9)	0.0007 (9)
C11	0.0196 (11)	0.0182 (12)	0.0173 (11)	0.0007 (9)	0.0029 (9)	0.0016 (9)
C12	0.0212 (12)	0.0191 (12)	0.0191 (11)	−0.0012 (9)	0.0065 (9)	−0.0035 (9)
C13	0.0169 (11)	0.0151 (11)	0.0237 (12)	0.0004 (9)	0.0064 (9)	0.0001 (9)
C14	0.0167 (11)	0.0156 (11)	0.0192 (12)	−0.0016 (9)	0.0042 (9)	0.0028 (9)
C15	0.0215 (12)	0.0163 (11)	0.0228 (12)	0.0022 (9)	0.0055 (10)	0.0023 (10)
C16	0.0216 (12)	0.0164 (11)	0.0231 (12)	0.0000 (9)	0.0047 (10)	0.0032 (9)
C17	0.0270 (13)	0.0199 (13)	0.0335 (14)	−0.0038 (10)	0.0115 (11)	0.0026 (11)
C18	0.0304 (14)	0.0196 (12)	0.0276 (14)	0.0019 (11)	0.0105 (11)	0.0062 (10)
C19	0.0195 (12)	0.0236 (13)	0.0211 (12)	0.0004 (9)	0.0063 (10)	0.0008 (10)
C20	0.0245 (12)	0.0225 (12)	0.0147 (11)	−0.0002 (10)	0.0044 (9)	0.0039 (10)
C21	0.0184 (11)	0.0208 (12)	0.0155 (11)	0.0007 (9)	−0.0003 (9)	0.0005 (9)
C22	0.0203 (12)	0.0210 (12)	0.0229 (12)	0.0028 (9)	0.0060 (10)	0.0028 (10)
C23	0.0201 (12)	0.0234 (13)	0.0226 (13)	0.0060 (10)	0.0035 (10)	0.0020 (10)
C24	0.0167 (11)	0.0188 (11)	0.0202 (12)	0.0047 (9)	0.0060 (9)	0.0007 (9)
O8	0.0226 (9)	0.0144 (8)	0.0204 (8)	0.0034 (7)	0.0053 (7)	0.0014 (7)
O9	0.0169 (8)	0.0215 (9)	0.0251 (9)	0.0043 (7)	0.0058 (7)	0.0070 (7)
O10	0.0314 (10)	0.0225 (9)	0.0271 (10)	−0.0073 (8)	0.0091 (8)	−0.0062 (8)
O11	0.0239 (9)	0.0184 (8)	0.0249 (9)	0.0003 (7)	0.0051 (7)	−0.0006 (7)
O12	0.0322 (10)	0.0177 (9)	0.0409 (11)	−0.0009 (8)	0.0191 (9)	−0.0054 (8)
O13	0.0161 (8)	0.0226 (9)	0.0247 (9)	0.0018 (7)	0.0056 (7)	0.0044 (7)
O14	0.0183 (8)	0.0163 (8)	0.0254 (9)	−0.0004 (7)	0.0008 (7)	0.0002 (7)
N3	0.0182 (10)	0.0131 (9)	0.0235 (10)	0.0001 (8)	0.0048 (8)	0.0002 (8)
N4	0.0194 (10)	0.0169 (10)	0.0219 (11)	0.0000 (8)	0.0054 (8)	−0.0001 (8)
C25	0.0163 (11)	0.0194 (12)	0.0211 (12)	−0.0018 (9)	0.0066 (9)	−0.0009 (10)
C26	0.0204 (12)	0.0213 (12)	0.0256 (13)	0.0012 (10)	0.0044 (10)	0.0036 (10)
C27	0.0268 (13)	0.0290 (14)	0.0207 (13)	−0.0016 (11)	0.0048 (10)	0.0033 (11)
C28	0.0262 (13)	0.0262 (13)	0.0235 (13)	−0.0022 (10)	0.0093 (10)	−0.0047 (11)
C29	0.0222 (12)	0.0194 (12)	0.0279 (13)	0.0011 (10)	0.0079 (10)	−0.0013 (10)
C30	0.0142 (11)	0.0171 (11)	0.0215 (12)	−0.0025 (9)	0.0043 (9)	−0.0003 (9)
C31	0.0180 (11)	0.0142 (11)	0.0266 (13)	0.0032 (9)	0.0067 (10)	0.0022 (10)
C32	0.0162 (11)	0.0225 (12)	0.0269 (13)	0.0022 (9)	0.0035 (10)	0.0049 (10)
C33	0.0160 (11)	0.0172 (11)	0.0207 (12)	−0.0024 (9)	−0.0012 (9)	0.0012 (10)
C34	0.0183 (12)	0.0185 (12)	0.0280 (13)	0.0000 (9)	−0.0004 (10)	0.0006 (10)
C35	0.0199 (12)	0.0192 (12)	0.0345 (14)	−0.0022 (10)	−0.0054 (10)	0.0082 (11)
C36	0.0219 (12)	0.0314 (14)	0.0232 (13)	−0.0083 (11)	−0.0015 (10)	0.0119 (11)
C37	0.0192 (12)	0.0292 (14)	0.0216 (12)	−0.0045 (10)	0.0019 (10)	0.0015 (10)
C38	0.0159 (11)	0.0165 (11)	0.0203 (12)	−0.0032 (9)	−0.0015 (9)	0.0019 (9)
C39	0.0265 (13)	0.0200 (12)	0.0211 (12)	−0.0014 (10)	0.0060 (10)	−0.0036 (10)
C40	0.0241 (13)	0.0209 (12)	0.0235 (13)	−0.0010 (10)	0.0041 (10)	−0.0037 (10)
C41	0.0300 (14)	0.0327 (15)	0.0266 (14)	−0.0131 (12)	0.0033 (11)	−0.0087 (12)
C42	0.0317 (15)	0.0216 (13)	0.0350 (15)	−0.0054 (11)	0.0140 (12)	−0.0050 (11)
C43	0.0204 (12)	0.0182 (11)	0.0249 (13)	0.0007 (10)	0.0053 (10)	0.0003 (10)
C44	0.0215 (12)	0.0125 (11)	0.0278 (13)	−0.0012 (9)	0.0055 (10)	0.0009 (10)
C45	0.0192 (12)	0.0153 (11)	0.0250 (12)	0.0022 (9)	0.0054 (10)	0.0019 (10)
C46	0.0199 (12)	0.0176 (12)	0.0264 (13)	0.0008 (9)	0.0081 (10)	0.0001 (10)
C47	0.0206 (12)	0.0198 (12)	0.0246 (12)	0.0030 (10)	0.0073 (10)	0.0008 (10)
C48	0.0136 (11)	0.0203 (12)	0.0227 (12)	0.0004 (9)	0.0059 (9)	0.0021 (10)

Geometric parameters (Å, º)

O1—C6	1.353 (3)	O8—C30	1.359 (3)
O1—C7	1.442 (3)	O8—C31	1.442 (3)
O2—C9	1.372 (3)	O9—C33	1.370 (3)
O2—C8	1.446 (3)	O9—C32	1.443 (3)
O3—C16	1.426 (3)	O10—C40	1.421 (3)
O3—C17	1.427 (3)	O10—C41	1.431 (3)
O4—C19	1.420 (3)	O11—C42	1.427 (3)
O4—C18	1.427 (3)	O11—C43	1.430 (3)
O5—C21	1.224 (3)	O12—C45	1.227 (3)
O6—C22	1.416 (3)	O13—C46	1.415 (3)
O6—C23	1.426 (3)	O13—C47	1.426 (3)
O7—C24	1.219 (3)	O14—C48	1.220 (3)
N1—C21	1.360 (3)	N3—C45	1.352 (3)
N1—C1	1.440 (3)	N3—C25	1.439 (3)
N1—C20	1.469 (3)	N3—C44	1.468 (3)
N2—C24	1.366 (3)	N4—C48	1.363 (3)
N2—C14	1.437 (3)	N4—C38	1.438 (3)
N2—C15	1.472 (3)	N4—C39	1.471 (3)
C1—C2	1.385 (3)	C25—C26	1.389 (4)
C1—C6	1.409 (3)	C25—C30	1.407 (3)
C2—C3	1.391 (4)	C26—C27	1.387 (4)
C2—H2A	0.9500	C26—H26A	0.9500
C3—C4	1.390 (4)	C27—C28	1.384 (4)
C3—H3A	0.9500	C27—H27A	0.9500
C4—C5	1.384 (4)	C28—C29	1.387 (4)
C4—H4A	0.9500	C28—H28A	0.9500
C5—C6	1.404 (3)	C29—C30	1.398 (3)
C5—H5A	0.9500	C29—H29A	0.9500
C7—C8	1.495 (3)	C31—C32	1.498 (3)
C7—H7A	0.9900	C31—H31A	0.9900
C7—H7B	0.9900	C31—H31B	0.9900
C8—H8A	0.9900	C32—H32A	0.9900
C8—H8B	0.9900	C32—H32B	0.9900
C9—C10	1.394 (3)	C33—C34	1.397 (3)
C9—C14	1.400 (3)	C33—C38	1.400 (3)
C10—C11	1.386 (3)	C34—C35	1.388 (4)
C10—H10A	0.9500	C34—H34A	0.9500
C11—C12	1.395 (3)	C35—C36	1.387 (4)
C11—H11A	0.9500	C35—H35A	0.9500
C12—C13	1.383 (4)	C36—C37	1.385 (4)
C12—H12A	0.9500	C36—H36A	0.9500
C13—C14	1.387 (3)	C37—C38	1.393 (3)
C13—H13A	0.9500	C37—H37A	0.9500
C15—C16	1.517 (3)	C39—C40	1.517 (4)
C15—H15A	0.9900	C39—H39A	0.9900
C15—H15B	0.9900	C39—H39B	0.9900
C16—H16A	0.9900	C40—H40A	0.9900
C16—H16B	0.9900	C40—H40B	0.9900
C17—C18	1.509 (4)	C41—C42	1.513 (4)
C17—H17A	0.9900	C41—H41A	0.9900
C17—H17B	0.9900	C41—H41B	0.9900
C18—H18A	0.9900	C42—H42A	0.9900
C18—H18B	0.9900	C42—H42B	0.9900
C19—C20	1.523 (4)	C43—C44	1.522 (4)
C19—H19A	0.9900	C43—H43A	0.9900
C19—H19B	0.9900	C43—H43B	0.9900
C20—H20A	0.9900	C44—H44A	0.9900
C20—H20B	0.9900	C44—H44B	0.9900
C21—C22	1.526 (3)	C45—C46	1.529 (3)
C22—H22A	0.9900	C46—H46A	0.9900
C22—H22B	0.9900	C46—H46B	0.9900
C23—C24	1.527 (3)	C47—C48	1.530 (3)
C23—H23A	0.9900	C47—H47A	0.9900
C23—H23B	0.9900	C47—H47B	0.9900
C6—O1—C7	117.21 (19)	C30—O8—C31	115.77 (18)
C9—O2—C8	115.21 (18)	C33—O9—C32	116.60 (18)
C16—O3—C17	114.11 (19)	C40—O10—C41	113.8 (2)
C19—O4—C18	114.81 (19)	C42—O11—C43	113.24 (19)
C22—O6—C23	113.39 (19)	C46—O13—C47	113.28 (19)
C21—N1—C1	125.7 (2)	C45—N3—C25	124.3 (2)
C21—N1—C20	118.5 (2)	C45—N3—C44	119.3 (2)
C1—N1—C20	115.8 (2)	C25—N3—C44	116.39 (19)
C24—N2—C14	117.4 (2)	C48—N4—C38	117.7 (2)
C24—N2—C15	126.2 (2)	C48—N4—C39	124.0 (2)
C14—N2—C15	116.3 (2)	C38—N4—C39	117.24 (19)
C2—C1—C6	119.9 (2)	C26—C25—C30	119.9 (2)
C2—C1—N1	119.1 (2)	C26—C25—N3	118.8 (2)
C6—C1—N1	120.7 (2)	C30—C25—N3	121.2 (2)
C1—C2—C3	120.9 (2)	C27—C26—C25	120.9 (2)
C1—C2—H2A	119.5	C27—C26—H26A	119.6
C3—C2—H2A	119.5	C25—C26—H26A	119.6
C4—C3—C2	119.3 (2)	C28—C27—C26	119.2 (2)
C4—C3—H3A	120.3	C28—C27—H27A	120.4
C2—C3—H3A	120.3	C26—C27—H27A	120.4
C5—C4—C3	120.6 (2)	C27—C28—C29	121.0 (2)
C5—C4—H4A	119.7	C27—C28—H28A	119.5
C3—C4—H4A	119.7	C29—C28—H28A	119.5
C4—C5—C6	120.5 (2)	C28—C29—C30	120.1 (2)
C4—C5—H5A	119.8	C28—C29—H29A	119.9
C6—C5—H5A	119.8	C30—C29—H29A	119.9
O1—C6—C5	124.8 (2)	O8—C30—C29	124.7 (2)
O1—C6—C1	116.4 (2)	O8—C30—C25	116.4 (2)
C5—C6—C1	118.7 (2)	C29—C30—C25	118.9 (2)
O1—C7—C8	108.26 (19)	O8—C31—C32	108.16 (19)
O1—C7—H7A	110.0	O8—C31—H31A	110.1
C8—C7—H7A	110.0	C32—C31—H31A	110.1
O1—C7—H7B	110.0	O8—C31—H31B	110.1
C8—C7—H7B	110.0	C32—C31—H31B	110.1
H7A—C7—H7B	108.4	H31A—C31—H31B	108.4
O2—C8—C7	108.67 (19)	O9—C32—C31	108.6 (2)
O2—C8—H8A	110.0	O9—C32—H32A	110.0
C7—C8—H8A	110.0	C31—C32—H32A	110.0
O2—C8—H8B	110.0	O9—C32—H32B	110.0
C7—C8—H8B	110.0	C31—C32—H32B	110.0
H8A—C8—H8B	108.3	H32A—C32—H32B	108.4
O2—C9—C10	122.6 (2)	O9—C33—C34	123.0 (2)
O2—C9—C14	118.3 (2)	O9—C33—C38	117.6 (2)
C10—C9—C14	119.0 (2)	C34—C33—C38	119.3 (2)
C11—C10—C9	119.9 (2)	C35—C34—C33	119.7 (3)
C11—C10—H10A	120.0	C35—C34—H34A	120.1
C9—C10—H10A	120.0	C33—C34—H34A	120.1
C10—C11—C12	121.1 (2)	C36—C35—C34	121.0 (2)
C10—C11—H11A	119.5	C36—C35—H35A	119.5
C12—C11—H11A	119.5	C34—C35—H35A	119.5
C13—C12—C11	118.9 (2)	C37—C36—C35	119.4 (2)
C13—C12—H12A	120.5	C37—C36—H36A	120.3
C11—C12—H12A	120.5	C35—C36—H36A	120.3
C12—C13—C14	120.7 (2)	C36—C37—C38	120.4 (3)
C12—C13—H13A	119.7	C36—C37—H37A	119.8
C14—C13—H13A	119.7	C38—C37—H37A	119.8
C13—C14—C9	120.4 (2)	C37—C38—C33	120.1 (2)
C13—C14—N2	119.5 (2)	C37—C38—N4	120.3 (2)
C9—C14—N2	120.0 (2)	C33—C38—N4	119.6 (2)
N2—C15—C16	110.9 (2)	N4—C39—C40	111.1 (2)
N2—C15—H15A	109.5	N4—C39—H39A	109.4
C16—C15—H15A	109.5	C40—C39—H39A	109.4
N2—C15—H15B	109.5	N4—C39—H39B	109.4
C16—C15—H15B	109.5	C40—C39—H39B	109.4
H15A—C15—H15B	108.0	H39A—C39—H39B	108.0
O3—C16—C15	106.44 (19)	O10—C40—C39	106.8 (2)
O3—C16—H16A	110.4	O10—C40—H40A	110.4
C15—C16—H16A	110.4	C39—C40—H40A	110.4
O3—C16—H16B	110.4	O10—C40—H40B	110.4
C15—C16—H16B	110.4	C39—C40—H40B	110.4
H16A—C16—H16B	108.6	H40A—C40—H40B	108.6
O3—C17—C18	114.7 (2)	O10—C41—C42	115.2 (2)
O3—C17—H17A	108.6	O10—C41—H41A	108.5
C18—C17—H17A	108.6	C42—C41—H41A	108.5
O3—C17—H17B	108.6	O10—C41—H41B	108.5
C18—C17—H17B	108.6	C42—C41—H41B	108.5
H17A—C17—H17B	107.6	H41A—C41—H41B	107.5
O4—C18—C17	109.0 (2)	O11—C42—C41	110.3 (2)
O4—C18—H18A	109.9	O11—C42—H42A	109.6
C17—C18—H18A	109.9	C41—C42—H42A	109.6
O4—C18—H18B	109.9	O11—C42—H42B	109.6
C17—C18—H18B	109.9	C41—C42—H42B	109.6
H18A—C18—H18B	108.3	H42A—C42—H42B	108.1
O4—C19—C20	113.6 (2)	O11—C43—C44	113.9 (2)
O4—C19—H19A	108.8	O11—C43—H43A	108.8
C20—C19—H19A	108.8	C44—C43—H43A	108.8
O4—C19—H19B	108.8	O11—C43—H43B	108.8
C20—C19—H19B	108.8	C44—C43—H43B	108.8
H19A—C19—H19B	107.7	H43A—C43—H43B	107.7
N1—C20—C19	112.0 (2)	N3—C44—C43	112.0 (2)
N1—C20—H20A	109.2	N3—C44—H44A	109.2
C19—C20—H20A	109.2	C43—C44—H44A	109.2
N1—C20—H20B	109.2	N3—C44—H44B	109.2
C19—C20—H20B	109.2	C43—C44—H44B	109.2
H20A—C20—H20B	107.9	H44A—C44—H44B	107.9
O5—C21—N1	121.8 (2)	O12—C45—N3	122.0 (2)
O5—C21—C22	121.7 (2)	O12—C45—C46	121.4 (2)
N1—C21—C22	116.4 (2)	N3—C45—C46	116.6 (2)
O6—C22—C21	113.1 (2)	O13—C46—C45	112.7 (2)
O6—C22—H22A	109.0	O13—C46—H46A	109.1
C21—C22—H22A	109.0	C45—C46—H46A	109.1
O6—C22—H22B	109.0	O13—C46—H46B	109.1
C21—C22—H22B	109.0	C45—C46—H46B	109.1
H22A—C22—H22B	107.8	H46A—C46—H46B	107.8
O6—C23—C24	111.2 (2)	O13—C47—C48	111.4 (2)
O6—C23—H23A	109.4	O13—C47—H47A	109.4
C24—C23—H23A	109.4	C48—C47—H47A	109.4
O6—C23—H23B	109.4	O13—C47—H47B	109.4
C24—C23—H23B	109.4	C48—C47—H47B	109.4
H23A—C23—H23B	108.0	H47A—C47—H47B	108.0
O7—C24—N2	121.3 (2)	O14—C48—N4	121.8 (2)
O7—C24—C23	120.6 (2)	O14—C48—C47	120.6 (2)
N2—C24—C23	118.0 (2)	N4—C48—C47	117.5 (2)
C21—N1—C1—C2	104.2 (3)	C45—N3—C25—C26	−101.0 (3)
C20—N1—C1—C2	−72.3 (3)	C44—N3—C25—C26	77.1 (3)
C21—N1—C1—C6	−81.5 (3)	C45—N3—C25—C30	83.2 (3)
C20—N1—C1—C6	102.0 (3)	C44—N3—C25—C30	−98.8 (3)
C6—C1—C2—C3	−1.0 (4)	C30—C25—C26—C27	−0.1 (4)
N1—C1—C2—C3	173.3 (2)	N3—C25—C26—C27	−176.0 (2)
C1—C2—C3—C4	−0.9 (4)	C25—C26—C27—C28	1.1 (4)
C2—C3—C4—C5	1.9 (4)	C26—C27—C28—C29	−1.4 (4)
C3—C4—C5—C6	−1.0 (4)	C27—C28—C29—C30	0.7 (4)
C7—O1—C6—C5	−7.4 (3)	C31—O8—C30—C29	6.3 (3)
C7—O1—C6—C1	172.6 (2)	C31—O8—C30—C25	−173.2 (2)
C4—C5—C6—O1	179.1 (2)	C28—C29—C30—O8	−179.1 (2)
C4—C5—C6—C1	−0.9 (3)	C28—C29—C30—C25	0.3 (4)
C2—C1—C6—O1	−178.1 (2)	C26—C25—C30—O8	178.9 (2)
N1—C1—C6—O1	7.7 (3)	N3—C25—C30—O8	−5.3 (3)
C2—C1—C6—C5	1.9 (3)	C26—C25—C30—C29	−0.6 (3)
N1—C1—C6—C5	−172.4 (2)	N3—C25—C30—C29	175.2 (2)
C6—O1—C7—C8	−173.84 (19)	C30—O8—C31—C32	172.0 (2)
C9—O2—C8—C7	163.45 (19)	C33—O9—C32—C31	−157.7 (2)
O1—C7—C8—O2	63.9 (2)	O8—C31—C32—O9	−64.2 (2)
C8—O2—C9—C10	−47.0 (3)	C32—O9—C33—C34	45.8 (3)
C8—O2—C9—C14	135.4 (2)	C32—O9—C33—C38	−137.4 (2)
O2—C9—C10—C11	−179.1 (2)	O9—C33—C34—C35	179.8 (2)
C14—C9—C10—C11	−1.6 (3)	C38—C33—C34—C35	3.1 (4)
C9—C10—C11—C12	0.1 (4)	C33—C34—C35—C36	0.0 (4)
C10—C11—C12—C13	0.7 (4)	C34—C35—C36—C37	−2.8 (4)
C11—C12—C13—C14	−0.2 (4)	C35—C36—C37—C38	2.4 (4)
C12—C13—C14—C9	−1.3 (4)	C36—C37—C38—C33	0.8 (4)
C12—C13—C14—N2	179.5 (2)	C36—C37—C38—N4	−178.1 (2)
O2—C9—C14—C13	179.8 (2)	O9—C33—C38—C37	179.6 (2)
C10—C9—C14—C13	2.1 (3)	C34—C33—C38—C37	−3.6 (4)
O2—C9—C14—N2	−1.0 (3)	O9—C33—C38—N4	−1.5 (3)
C10—C9—C14—N2	−178.6 (2)	C34—C33—C38—N4	175.3 (2)
C24—N2—C14—C13	−112.3 (2)	C48—N4—C38—C37	117.8 (3)
C15—N2—C14—C13	71.7 (3)	C39—N4—C38—C37	−73.8 (3)
C24—N2—C14—C9	68.5 (3)	C48—N4—C38—C33	−61.1 (3)
C15—N2—C14—C9	−107.6 (2)	C39—N4—C38—C33	107.3 (3)
C24—N2—C15—C16	−92.9 (3)	C48—N4—C39—C40	83.7 (3)
C14—N2—C15—C16	82.8 (3)	C38—N4—C39—C40	−83.9 (3)
C17—O3—C16—C15	178.7 (2)	C41—O10—C40—C39	−175.3 (2)
N2—C15—C16—O3	−179.8 (2)	N4—C39—C40—O10	−172.5 (2)
C16—O3—C17—C18	66.6 (3)	C40—O10—C41—C42	−69.2 (3)
C19—O4—C18—C17	−170.7 (2)	C43—O11—C42—C41	170.2 (2)
O3—C17—C18—O4	−84.8 (3)	O10—C41—C42—O11	80.5 (3)
C18—O4—C19—C20	−77.5 (3)	C42—O11—C43—C44	76.9 (3)
C21—N1—C20—C19	106.3 (2)	C45—N3—C44—C43	−104.4 (3)
C1—N1—C20—C19	−76.9 (3)	C25—N3—C44—C43	77.4 (3)
O4—C19—C20—N1	−65.7 (3)	O11—C43—C44—N3	65.3 (3)
C1—N1—C21—O5	−171.7 (2)	C25—N3—C45—O12	171.5 (2)
C20—N1—C21—O5	4.7 (3)	C44—N3—C45—O12	−6.5 (4)
C1—N1—C21—C22	9.5 (3)	C25—N3—C45—C46	−9.6 (3)
C20—N1—C21—C22	−174.1 (2)	C44—N3—C45—C46	172.4 (2)
C23—O6—C22—C21	−69.4 (3)	C47—O13—C46—C45	67.1 (3)
O5—C21—C22—O6	11.7 (3)	O12—C45—C46—O13	−4.1 (3)
N1—C21—C22—O6	−169.5 (2)	N3—C45—C46—O13	177.0 (2)
C22—O6—C23—C24	−67.1 (3)	C46—O13—C47—C48	70.2 (3)
C14—N2—C24—O7	5.4 (3)	C38—N4—C48—O14	−6.7 (3)
C15—N2—C24—O7	−179.1 (2)	C39—N4—C48—O14	−174.3 (2)
C14—N2—C24—C23	−175.8 (2)	C38—N4—C48—C47	175.3 (2)
C15—N2—C24—C23	−0.3 (3)	C39—N4—C48—C47	7.7 (3)
O6—C23—C24—O7	−40.8 (3)	O13—C47—C48—O14	28.0 (3)
O6—C23—C24—N2	140.3 (2)	O13—C47—C48—N4	−154.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O14^i	0.99	2.59	3.136 (3)	115
C10—H10A···O14^i	0.95	2.48	3.216 (3)	134
C16—H16B···O4	0.99	2.49	3.033 (3)	114
C19—H19A···O6^ii	0.99	2.52	3.345 (3)	140
C22—H22B···O1	0.99	2.58	3.219 (3)	122
C23—H23A···O4^iii	0.99	2.48	3.243 (3)	134
C23—H23B···O5	0.99	2.22	2.891 (3)	124
C31—H31A···O7^iv	0.99	2.28	3.125 (3)	143
C31—H31B···O14^iii	0.99	2.48	3.297 (3)	139
C40—H40A···O11	0.99	2.49	3.030 (3)	114
C43—H43B···O13^iii	0.99	2.45	3.361 (3)	152
C44—H44A···O5	0.99	2.65	3.228 (3)	117
C46—H46A···O8	0.99	2.59	3.280 (3)	127
C47—H47A···O12	0.99	2.21	2.878 (3)	123
C47—H47B···O11^ii	0.99	2.60	3.442 (3)	143

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