meso-5,10,15,20-Tetra-kis(4-hy-droxy-3-meth-oxy-phen-yl)porphyrin propionic acid monosolvate.

In the title compound, C(48)H(38)N(4)O(8)·C(3)H(6)O(2), the porphyrin mol-ecule is centrosymmetric. The propionic acid solvent mol-ecule is disordered over two sets of sites with equal occupancy factors. The porphyrin central core is almost planar, with an r.m.s. deviation of the fitted atoms of 0.045 Å. The substituent benzene rings make dihedral angles of 70.37 (4) and 66.95 (4)° with respect to the porphyrin core plane. The crystal structure is stabilized by an inter-esting network of hydrogen bonds. Porphyrin mol-ecules are connected by O-H⋯O hydrogen bonds creating ribbons running along the [101] direction. Weak C-H⋯O hydrogen bonds connect separate mol-ecular ribbons in the [110] direction, creating (-111) layers. Intra-molecular N-H⋯N hydrogen bonds also occur. The propionic acid molecules are connected by pairs of -H⋯O hydrogen bonds, creating dimers.

Related literature

For the biological activity and potential applications of porphyrin mol­ecules, see: Allison et al. (2004 ▶); Dougherty et al. (1998 ▶); Agostinis et al. (2011 ▶); Szurko et al. (2009 ▶). For spectroscopic data, see Bonar-Law (1996 ▶).

Experimental

Crystal data

C48H38N4O8·C3H6O2

M = 872.90

Triclinic,

a = 6.8715 (5) Å

b = 12.0783 (7) Å

c = 14.3772 (10) Å

α = 112.850 (6)°

β = 98.560 (5)°

γ = 97.480 (5)°

V = 1063.97 (12) Å3

Z = 1

Cu Kα radiation

μ = 0.78 mm−1

T = 100 K

0.10 × 0.03 × 0.02 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.926, T max = 0.985

9919 measured reflections

3688 independent reflections

3098 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.03

3688 reflections

339 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036495/bt5999sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036495/bt5999Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C48H38N4O8·C3H6O2	Z = 1
Mr = 872.90	F(000) = 458
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.8715 (5) Å	Cell parameters from 4163 reflections
b = 12.0783 (7) Å	θ = 3.4–65.9°
c = 14.3772 (10) Å	µ = 0.78 mm−1
α = 112.850 (6)°	T = 100 K
β = 98.560 (5)°	Polyhedron, black
γ = 97.480 (5)°	0.10 × 0.03 × 0.02 mm
V = 1063.97 (12) Å3

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3688 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3098 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.028
Detector resolution: 10.4498 pixels mm-1	θmax = 66.0°, θmin = 3.4°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→14
Tmin = 0.926, Tmax = 0.985	l = −15→17
9919 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.3935P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3688 reflections	Δρmax = 0.22 e Å−3
339 parameters	Δρmin = −0.25 e Å−3
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0040 (5)

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.19 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	−0.28230 (18)	0.01112 (11)	0.33140 (9)	0.0254 (3)
H1O	−0.211 (3)	−0.042 (2)	0.3180 (17)	0.038*
O2	1.21357 (17)	0.83439 (12)	0.45275 (9)	0.0294 (3)
H2O	1.190 (3)	0.882 (2)	0.5143 (19)	0.044*
O3	−0.00783 (17)	−0.03851 (10)	0.21636 (8)	0.0237 (3)
O4	0.87195 (16)	0.87779 (11)	0.51416 (8)	0.0256 (3)
N1	0.1653 (2)	0.46061 (12)	0.11394 (10)	0.0188 (3)
H1N	0.101 (3)	0.4735 (17)	0.0650 (15)	0.023*
N2	−0.24395 (19)	0.37519 (11)	−0.01361 (10)	0.0186 (3)
C1	−0.2385 (2)	0.08075 (14)	0.27810 (12)	0.0216 (4)
C2	−0.3381 (3)	0.17440 (15)	0.28535 (13)	0.0256 (4)
H2	−0.4365	0.1896	0.3262	0.031*
C3	−0.2950 (2)	0.24694 (15)	0.23292 (13)	0.0241 (4)
H3	−0.3647	0.3114	0.2381	0.029*
C4	−0.1513 (2)	0.22622 (14)	0.17301 (12)	0.0198 (3)
C5	−0.0510 (2)	0.13016 (14)	0.16546 (12)	0.0205 (3)
H5	0.0473	0.1147	0.1246	0.025*
C6	−0.0946 (2)	0.05773 (14)	0.21729 (12)	0.0201 (3)
C7	−0.1047 (2)	0.30658 (14)	0.11882 (11)	0.0188 (3)
C8	−0.2574 (2)	0.30429 (14)	0.04101 (12)	0.0194 (3)
C9	−0.4521 (2)	0.22058 (15)	0.00422 (12)	0.0228 (4)
H9	−0.4984	0.1625	0.0297	0.027*
C10	−0.5542 (2)	0.24117 (15)	−0.07284 (12)	0.0224 (4)
H10	−0.689 (3)	0.1991 (18)	−0.1155 (15)	0.027*
C11	−0.4238 (2)	0.33809 (14)	−0.08348 (12)	0.0193 (3)
C12	0.4759 (2)	0.61748 (14)	0.15889 (12)	0.0188 (3)
C13	0.3540 (2)	0.52417 (14)	0.17144 (12)	0.0189 (3)
C14	0.3994 (2)	0.48061 (14)	0.24959 (12)	0.0225 (4)
H14	0.5208	0.5076	0.3007	0.027*
C15	0.2393 (2)	0.39374 (14)	0.23837 (12)	0.0228 (4)
H15	0.2294	0.3494	0.2800	0.027*
C16	0.0885 (2)	0.38112 (14)	0.15268 (12)	0.0195 (3)
C17	0.6721 (2)	0.67684 (14)	0.23575 (12)	0.0191 (3)
C18	0.8540 (2)	0.65879 (15)	0.20740 (13)	0.0247 (4)
H18	0.8553	0.6091	0.1377	0.030*
C19	1.0343 (2)	0.71304 (15)	0.28061 (13)	0.0260 (4)
H19	1.1579	0.7003	0.2604	0.031*
C20	1.0351 (2)	0.78502 (14)	0.38213 (12)	0.0217 (3)
C21	0.8527 (2)	0.80458 (14)	0.41172 (12)	0.0194 (3)
C22	0.6726 (2)	0.75083 (14)	0.33878 (12)	0.0192 (3)
H22	0.5490	0.7643	0.3589	0.023*
C23	0.6888 (3)	0.8927 (2)	0.54936 (14)	0.0344 (5)
H23A	0.600 (4)	0.933 (2)	0.5120 (19)	0.052*
H23B	0.729 (4)	0.944 (2)	0.624 (2)	0.052*
H23C	0.608 (4)	0.811 (2)	0.5363 (19)	0.052*
C24	0.1311 (3)	−0.07391 (17)	0.15062 (14)	0.0321 (4)
H24A	0.2460	−0.0054	0.1724	0.048*
H24B	0.0641	−0.0956	0.0789	0.048*
H24C	0.1785	−0.1450	0.1556	0.048*
O6	0.3201 (9)	0.5783 (3)	0.5140 (3)	0.1001 (17)	0.50
O5	0.2982 (10)	0.3840 (4)	0.4875 (3)	0.0992 (17)	0.50
H5A	0.4195	0.4002	0.4851	0.149*	0.50
C25	0.2215 (14)	0.4812 (6)	0.5036 (4)	0.078 (2)	0.50
C26	0.0013 (18)	0.4670 (7)	0.5103 (7)	0.086 (3)	0.50
H26A	−0.0735	0.3851	0.4583	0.103*	0.50
H26B	−0.0093	0.4716	0.5796	0.103*	0.50
C27	−0.0933 (19)	0.5642 (10)	0.4919 (9)	0.099 (4)	0.50
H27A	−0.2359	0.5497	0.4941	0.148*	0.50
H27B	−0.0808	0.5611	0.4240	0.148*	0.50
H27C	−0.0250	0.6452	0.5458	0.148*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0275 (6)	0.0259 (6)	0.0237 (6)	0.0023 (5)	0.0049 (5)	0.0125 (5)
O2	0.0141 (6)	0.0390 (7)	0.0221 (6)	0.0023 (5)	−0.0026 (5)	0.0022 (5)
O3	0.0252 (6)	0.0214 (6)	0.0243 (6)	0.0060 (5)	0.0046 (5)	0.0092 (5)
O4	0.0159 (6)	0.0363 (7)	0.0161 (5)	0.0004 (5)	0.0021 (4)	0.0039 (5)
N1	0.0152 (6)	0.0196 (7)	0.0180 (7)	0.0012 (5)	−0.0007 (5)	0.0065 (5)
N2	0.0166 (6)	0.0187 (6)	0.0171 (6)	0.0030 (5)	0.0012 (5)	0.0051 (5)
C1	0.0211 (8)	0.0212 (8)	0.0180 (8)	−0.0023 (6)	−0.0003 (6)	0.0070 (6)
C2	0.0223 (8)	0.0285 (9)	0.0253 (8)	0.0037 (7)	0.0071 (7)	0.0102 (7)
C3	0.0226 (8)	0.0243 (8)	0.0260 (8)	0.0060 (7)	0.0053 (7)	0.0107 (7)
C4	0.0176 (8)	0.0195 (8)	0.0172 (7)	−0.0008 (6)	−0.0016 (6)	0.0055 (6)
C5	0.0177 (8)	0.0214 (8)	0.0176 (7)	0.0004 (6)	0.0010 (6)	0.0051 (6)
C6	0.0191 (8)	0.0179 (7)	0.0171 (7)	0.0001 (6)	−0.0024 (6)	0.0043 (6)
C7	0.0181 (8)	0.0184 (7)	0.0172 (7)	0.0026 (6)	0.0030 (6)	0.0053 (6)
C8	0.0188 (8)	0.0179 (7)	0.0178 (7)	0.0017 (6)	0.0032 (6)	0.0044 (6)
C9	0.0203 (8)	0.0226 (8)	0.0221 (8)	−0.0012 (6)	0.0018 (6)	0.0086 (7)
C10	0.0168 (8)	0.0235 (8)	0.0212 (8)	−0.0011 (6)	−0.0001 (6)	0.0064 (7)
C11	0.0163 (7)	0.0186 (8)	0.0176 (7)	0.0018 (6)	0.0020 (6)	0.0032 (6)
C12	0.0158 (8)	0.0180 (7)	0.0176 (7)	0.0035 (6)	0.0019 (6)	0.0028 (6)
C13	0.0161 (7)	0.0179 (7)	0.0178 (7)	0.0029 (6)	0.0012 (6)	0.0035 (6)
C14	0.0177 (8)	0.0216 (8)	0.0219 (8)	0.0017 (6)	−0.0038 (6)	0.0062 (7)
C15	0.0225 (8)	0.0218 (8)	0.0220 (8)	0.0028 (6)	−0.0001 (6)	0.0094 (7)
C16	0.0190 (8)	0.0183 (7)	0.0185 (7)	0.0033 (6)	0.0023 (6)	0.0057 (6)
C17	0.0164 (8)	0.0169 (7)	0.0208 (8)	0.0005 (6)	0.0001 (6)	0.0069 (6)
C18	0.0195 (8)	0.0273 (9)	0.0192 (8)	0.0046 (7)	0.0017 (6)	0.0023 (7)
C19	0.0167 (8)	0.0298 (9)	0.0255 (9)	0.0061 (7)	0.0038 (7)	0.0050 (7)
C20	0.0150 (8)	0.0233 (8)	0.0220 (8)	0.0008 (6)	−0.0013 (6)	0.0071 (7)
C21	0.0183 (8)	0.0199 (8)	0.0170 (7)	0.0011 (6)	0.0023 (6)	0.0059 (6)
C22	0.0145 (7)	0.0209 (8)	0.0203 (8)	0.0010 (6)	0.0018 (6)	0.0081 (6)
C23	0.0182 (9)	0.0506 (12)	0.0210 (9)	0.0000 (8)	0.0060 (7)	0.0027 (8)
C24	0.0372 (10)	0.0318 (9)	0.0324 (10)	0.0161 (8)	0.0136 (8)	0.0138 (8)
O6	0.192 (5)	0.039 (2)	0.067 (3)	0.009 (3)	0.050 (3)	0.0162 (18)
O5	0.165 (5)	0.054 (2)	0.073 (3)	0.006 (3)	−0.001 (3)	0.036 (2)
C25	0.157 (7)	0.038 (3)	0.025 (2)	0.001 (4)	−0.001 (3)	0.011 (2)
C26	0.153 (8)	0.037 (5)	0.050 (3)	0.002 (5)	−0.017 (5)	0.020 (3)
C27	0.138 (11)	0.053 (6)	0.092 (6)	0.010 (5)	−0.026 (6)	0.037 (4)

O1—C1	1.3742 (19)	C12—C11i	1.406 (2)
O1—H1O	0.84 (2)	C12—C17	1.497 (2)
O2—C20	1.3637 (19)	C13—C14	1.426 (2)
O2—H2O	0.90 (2)	C14—C15	1.361 (2)
O3—C6	1.3704 (19)	C14—H14	0.9500
O3—C24	1.431 (2)	C15—C16	1.431 (2)
O4—C21	1.3670 (19)	C15—H15	0.9500
O4—C23	1.432 (2)	C17—C18	1.389 (2)
N1—C16	1.372 (2)	C17—C22	1.401 (2)
N1—C13	1.372 (2)	C18—C19	1.392 (2)
N1—H1N	0.85 (2)	C18—H18	0.9500
N2—C11	1.369 (2)	C19—C20	1.377 (2)
N2—C8	1.372 (2)	C19—H19	0.9500
C1—C2	1.375 (2)	C20—C21	1.402 (2)
C1—C6	1.400 (2)	C21—C22	1.389 (2)
C2—C3	1.391 (2)	C22—H22	0.9500
C2—H2	0.9500	C23—H23A	1.04 (3)
C3—C4	1.389 (2)	C23—H23B	0.99 (3)
C3—H3	0.9500	C23—H23C	1.00 (3)
C4—C5	1.402 (2)	C24—H24A	0.9800
C4—C7	1.494 (2)	C24—H24B	0.9800
C5—C6	1.384 (2)	C24—H24C	0.9800
C5—H5	0.9500	O6—C25	1.218 (8)
C7—C16	1.402 (2)	O5—C25	1.303 (9)
C7—C8	1.405 (2)	O5—H5A	0.8400
C8—C9	1.454 (2)	C25—C26	1.522 (16)
C9—C10	1.345 (2)	C26—C27	1.503 (13)
C9—H9	0.9500	C26—H26A	0.9900
C10—C11	1.450 (2)	C26—H26B	0.9900
C10—H10	0.98 (2)	C27—H27A	0.9800
C11—C12i	1.406 (2)	C27—H27B	0.9800
C12—C13	1.401 (2)	C27—H27C	0.9800
C1—O1—H1O	107.0 (15)	C14—C15—H15	126.1
C20—O2—H2O	108.6 (15)	C16—C15—H15	126.1
C6—O3—C24	117.77 (13)	N1—C16—C7	126.76 (14)
C21—O4—C23	116.35 (12)	N1—C16—C15	106.89 (13)
C16—N1—C13	110.09 (13)	C7—C16—C15	126.26 (14)
C16—N1—H1N	124.7 (13)	C18—C17—C22	119.17 (14)
C13—N1—H1N	124.9 (13)	C18—C17—C12	121.39 (14)
C11—N2—C8	105.46 (12)	C22—C17—C12	119.44 (14)
O1—C1—C2	118.99 (15)	C17—C18—C19	120.38 (15)
O1—C1—C6	121.02 (15)	C17—C18—H18	119.8
C2—C1—C6	119.99 (15)	C19—C18—H18	119.8
C1—C2—C3	120.07 (15)	C20—C19—C18	120.56 (15)
C1—C2—H2	120.0	C20—C19—H19	119.7
C3—C2—H2	120.0	C18—C19—H19	119.7
C4—C3—C2	120.75 (15)	O2—C20—C19	119.30 (15)
C4—C3—H3	119.6	O2—C20—C21	121.01 (14)
C2—C3—H3	119.6	C19—C20—C21	119.68 (14)
C3—C4—C5	118.91 (15)	O4—C21—C22	125.60 (14)
C3—C4—C7	119.91 (14)	O4—C21—C20	114.51 (13)
C5—C4—C7	121.18 (14)	C22—C21—C20	119.88 (14)
C6—C5—C4	120.30 (15)	C21—C22—C17	120.32 (15)
C6—C5—H5	119.9	C21—C22—H22	119.8
C4—C5—H5	119.9	C17—C22—H22	119.8
O3—C6—C5	126.06 (14)	O4—C23—H23A	112.4 (14)
O3—C6—C1	113.96 (13)	O4—C23—H23B	105.9 (14)
C5—C6—C1	119.98 (15)	H23A—C23—H23B	111.4 (19)
C16—C7—C8	125.43 (14)	O4—C23—H23C	109.9 (14)
C16—C7—C4	116.49 (14)	H23A—C23—H23C	108 (2)
C8—C7—C4	118.05 (13)	H23B—C23—H23C	109 (2)
N2—C8—C7	125.96 (14)	O3—C24—H24A	109.5
N2—C8—C9	110.38 (13)	O3—C24—H24B	109.5
C7—C8—C9	123.62 (14)	H24A—C24—H24B	109.5
C10—C9—C8	106.76 (14)	O3—C24—H24C	109.5
C10—C9—H9	126.6	H24A—C24—H24C	109.5
C8—C9—H9	126.6	H24B—C24—H24C	109.5
C9—C10—C11	106.70 (14)	C25—O5—H5A	109.5
C9—C10—H10	128.0 (11)	O6—C25—O5	122.2 (9)
C11—C10—H10	125.3 (11)	O6—C25—C26	121.8 (7)
N2—C11—C12i	125.73 (14)	O5—C25—C26	116.0 (7)
N2—C11—C10	110.70 (14)	C27—C26—C25	112.1 (6)
C12i—C11—C10	123.52 (14)	C27—C26—H26A	109.2
C13—C12—C11i	125.08 (14)	C25—C26—H26A	109.2
C13—C12—C17	116.23 (14)	C27—C26—H26B	109.2
C11i—C12—C17	118.62 (13)	C25—C26—H26B	109.2
N1—C13—C12	126.83 (14)	H26A—C26—H26B	107.9
N1—C13—C14	106.81 (13)	C26—C27—H27A	109.5
C12—C13—C14	126.31 (14)	C26—C27—H27B	109.5
C15—C14—C13	108.34 (14)	H27A—C27—H27B	109.5
C15—C14—H14	125.8	C26—C27—H27C	109.5
C13—C14—H14	125.8	H27A—C27—H27C	109.5
C14—C15—C16	107.86 (14)	H27B—C27—H27C	109.5
O1—C1—C2—C3	179.38 (14)	C17—C12—C13—N1	176.90 (14)
C6—C1—C2—C3	−0.5 (2)	C11i—C12—C13—C14	−177.37 (15)
C1—C2—C3—C4	−0.1 (2)	C17—C12—C13—C14	−0.3 (2)
C2—C3—C4—C5	0.5 (2)	N1—C13—C14—C15	−0.45 (18)
C2—C3—C4—C7	−178.92 (14)	C12—C13—C14—C15	177.19 (15)
C3—C4—C5—C6	−0.2 (2)	C13—C14—C15—C16	−0.24 (18)
C7—C4—C5—C6	179.19 (14)	C13—N1—C16—C7	175.63 (15)
C24—O3—C6—C5	−4.5 (2)	C13—N1—C16—C15	−1.14 (17)
C24—O3—C6—C1	175.86 (14)	C8—C7—C16—N1	−2.8 (3)
C4—C5—C6—O3	−179.98 (13)	C4—C7—C16—N1	179.17 (14)
C4—C5—C6—C1	−0.4 (2)	C8—C7—C16—C15	173.42 (15)
O1—C1—C6—O3	0.5 (2)	C4—C7—C16—C15	−4.7 (2)
C2—C1—C6—O3	−179.61 (14)	C14—C15—C16—N1	0.84 (18)
O1—C1—C6—C5	−179.11 (13)	C14—C15—C16—C7	−175.96 (15)
C2—C1—C6—C5	0.8 (2)	C13—C12—C17—C18	110.22 (18)
C3—C4—C7—C16	113.71 (17)	C11i—C12—C17—C18	−72.5 (2)
C5—C4—C7—C16	−65.69 (19)	C13—C12—C17—C22	−68.89 (19)
C3—C4—C7—C8	−64.5 (2)	C11i—C12—C17—C22	108.39 (17)
C5—C4—C7—C8	116.09 (16)	C22—C17—C18—C19	0.3 (2)
C11—N2—C8—C7	177.38 (15)	C12—C17—C18—C19	−178.78 (15)
C11—N2—C8—C9	−0.18 (17)	C17—C18—C19—C20	0.2 (3)
C16—C7—C8—N2	−0.8 (3)	C18—C19—C20—O2	178.29 (16)
C4—C7—C8—N2	177.23 (14)	C18—C19—C20—C21	−0.5 (3)
C16—C7—C8—C9	176.43 (15)	C23—O4—C21—C22	4.4 (2)
C4—C7—C8—C9	−5.5 (2)	C23—O4—C21—C20	−175.46 (16)
N2—C8—C9—C10	0.38 (18)	O2—C20—C21—O4	1.4 (2)
C7—C8—C9—C10	−177.25 (15)	C19—C20—C21—O4	−179.76 (15)
C8—C9—C10—C11	−0.40 (18)	O2—C20—C21—C22	−178.45 (15)
C8—N2—C11—C12i	−177.59 (15)	C19—C20—C21—C22	0.4 (2)
C8—N2—C11—C10	−0.07 (17)	O4—C21—C22—C17	−179.70 (14)
C9—C10—C11—N2	0.31 (18)	C20—C21—C22—C17	0.2 (2)
C9—C10—C11—C12i	177.89 (15)	C18—C17—C22—C21	−0.5 (2)
C16—N1—C13—C12	−176.62 (15)	C12—C17—C22—C21	178.62 (14)
C16—N1—C13—C14	1.00 (17)	O6—C25—C26—C27	20.7 (8)
C11i—C12—C13—N1	−0.2 (3)	O5—C25—C26—C27	−160.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.85 (2)	2.392 (19)	2.9286 (19)	121.4 (15)
N1—H1N···N2i	0.85 (2)	2.377 (19)	2.9121 (19)	121.2 (15)
O1—H1O···O3	0.84 (2)	2.17 (2)	2.6655 (17)	117.4 (19)
O2—H2O···O4	0.90 (2)	2.18 (2)	2.6726 (16)	113.8 (18)
O2—H2O···O1ii	0.90 (2)	2.03 (2)	2.8588 (17)	151 (2)
C10—H10···O3iii	0.98 (2)	2.46 (2)	3.4085 (19)	162.0 (16)
C23—H23B···O3ii	0.99 (3)	2.51 (3)	3.383 (2)	147.3 (19)
C23—H23C···O5ii	1.00 (3)	2.43 (3)	3.189 (5)	132.3 (19)
O5—H5A···O6ii	0.84	1.77	2.608 (9)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2	0.85 (2)	2.392 (19)	2.9286 (19)	121.4 (15)
N1—H1N⋯N2i	0.85 (2)	2.377 (19)	2.9121 (19)	121.2 (15)
O1—H1O⋯O3	0.84 (2)	2.17 (2)	2.6655 (17)	117.4 (19)
O2—H2O⋯O4	0.90 (2)	2.18 (2)	2.6726 (16)	113.8 (18)
O2—H2O⋯O1ii	0.90 (2)	2.03 (2)	2.8588 (17)	151 (2)
C10—H10⋯O3iii	0.98 (2)	2.46 (2)	3.4085 (19)	162.0 (16)
C23—H23B⋯O3ii	0.99 (3)	2.51 (3)	3.383 (2)	147.3 (19)
C23—H23C⋯O5ii	1.00 (3)	2.43 (3)	3.189 (5)	132.3 (19)
O5—H5A⋯O6ii	0.84	1.77	2.608 (9)	173

Symmetry codes: (i) ; (ii) ; (iii) .