5,10,15,20-Tetra­kis(4-pyrid­yl)porphyrin tris(acetic acid) clathrate

The crystal structure of the title compound, C₄₀H₂₆N₈·3CH₃COOH, has been determined at ca 110 K. The compound crystallizes as an acetic acid clathrate in which three guest mol­ecules are inter­calated between layered zones of offset stacked porphyrins. Two of the pyrid­yl groups of the latter are involved in hydrogen bonds with the acetic acid.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.134
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O49    -   H49    ...       1.06 Ang.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O53    -   H53    ...       1.03 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C2 H4 O2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C2 H4 O2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              C2 H4 O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

---

Computing details

Data collection: Collect (Nonius, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SIR97 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

5,10,15,20-Tetrakis(4-pyridyl)porphyrin triacetic acid clathrate

Crystal data

C40H26N8·3C2H4O2	Z = 2
Mr = 798.84	F(000) = 836
Triclinic, P1	Dx = 1.381 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4672 (2) Å	Cell parameters from 6720 reflections
b = 11.2549 (2) Å	θ = 2.0–27.5°
c = 17.1109 (4) Å	µ = 0.09 mm^−1
α = 92.2350 (12)°	T = 110 K
β = 106.5621 (10)°	Chunk, violet
γ = 94.8600 (12)°	0.40 × 0.35 × 0.20 mm
V = 1921.00 (7) Å^3

Data collection

Nonius KappaCCD diffractometer	6790 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 27.5°, θmin = 2.0°
Detector resolution: 56 pixels mm^-1	h = −13→13
1° φ and ω scans	k = −14→14
20904 measured reflections	l = −22→21
8806 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0724P)^2 + 0.4868P] where P = (Fo^2 + 2Fc^2)/3
8806 reflections	(Δ/σ)max = 0.041
549 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	1.04504 (14)	0.17707 (12)	0.63322 (9)	0.0194 (3)
C2	1.14417 (15)	0.24737 (13)	0.69775 (9)	0.0218 (3)
H2	1.1661	0.2342	0.7543	0.026*
C3	1.20074 (15)	0.33592 (13)	0.66321 (9)	0.0217 (3)
H3	1.2704	0.3953	0.6913	0.026*
C4	1.13707 (14)	0.32416 (12)	0.57674 (9)	0.0196 (3)
C5	1.16583 (14)	0.39973 (12)	0.51946 (9)	0.0192 (3)
C6	1.08984 (14)	0.39780 (12)	0.43662 (9)	0.0190 (3)
C7	1.11663 (15)	0.47875 (13)	0.37821 (9)	0.0216 (3)
H7	1.1908	0.5378	0.3876	0.026*
C8	1.01741 (15)	0.45500 (13)	0.30833 (10)	0.0224 (3)
H8	1.0070	0.4948	0.2593	0.027*
C9	0.92902 (14)	0.35681 (12)	0.32215 (9)	0.0195 (3)
C10	0.80912 (14)	0.30917 (13)	0.26436 (9)	0.0200 (3)
C11	0.72122 (15)	0.21401 (13)	0.27506 (9)	0.0203 (3)
C12	0.59879 (15)	0.16597 (13)	0.21638 (10)	0.0234 (3)
H12	0.5600	0.1953	0.1645	0.028*
C13	0.54822 (15)	0.07064 (13)	0.24847 (9)	0.0226 (3)
H13	0.4673	0.0217	0.2231	0.027*
C14	0.63861 (14)	0.05698 (12)	0.32733 (9)	0.0194 (3)
C15	0.62511 (14)	−0.03164 (12)	0.38098 (9)	0.0186 (3)
C16	0.70927 (14)	−0.03720 (12)	0.46074 (9)	0.0196 (3)
C17	0.69695 (15)	−0.13102 (12)	0.51440 (9)	0.0210 (3)
H17	0.6338	−0.1999	0.5014	0.025*
C18	0.79168 (15)	−0.10257 (12)	0.58628 (9)	0.0209 (3)
H18	0.8083	−0.1477	0.6333	0.025*
C19	0.86329 (14)	0.01021 (12)	0.57807 (9)	0.0196 (3)
C20	0.96562 (14)	0.07407 (12)	0.64173 (9)	0.0195 (3)
N21	1.04089 (12)	0.22811 (10)	0.56105 (8)	0.0195 (3)
H21	0.9802	0.2053	0.5056	0.050*
N22	0.97654 (12)	0.32284 (10)	0.40033 (8)	0.0198 (3)
N23	0.74181 (12)	0.14645 (10)	0.34195 (7)	0.0194 (3)
H23	0.8228	0.1598	0.3893	0.050*
N24	0.81335 (12)	0.04672 (10)	0.50079 (7)	0.0202 (3)
C25	1.28839 (14)	0.48695 (12)	0.54834 (9)	0.0196 (3)
C26	1.28498 (15)	0.60944 (13)	0.53914 (9)	0.0218 (3)
H26	1.2023	0.6413	0.5160	0.026*
C27	1.40371 (16)	0.68399 (13)	0.56418 (10)	0.0240 (3)
H27	1.3991	0.7668	0.5565	0.029*
N28	1.52389 (13)	0.64752 (11)	0.59835 (8)	0.0269 (3)
C29	1.52552 (16)	0.53023 (14)	0.60905 (10)	0.0267 (3)
H29	1.6091	0.5016	0.6347	0.032*
C30	1.41306 (15)	0.44825 (13)	0.58510 (9)	0.0223 (3)
H30	1.4209	0.3660	0.5937	0.027*
C31	0.77163 (15)	0.36474 (13)	0.18429 (9)	0.0214 (3)
C32	0.84752 (15)	0.35626 (13)	0.12991 (9)	0.0235 (3)
H32	0.9241	0.3129	0.1428	0.028*
C33	0.81133 (16)	0.41098 (14)	0.05716 (10)	0.0262 (3)
H33	0.8645	0.4043	0.0208	0.031*
N34	0.70439 (13)	0.47324 (12)	0.03548 (8)	0.0266 (3)
C35	0.63162 (16)	0.48222 (14)	0.08809 (10)	0.0264 (3)
H35	0.5565	0.5272	0.0739	0.032*
C36	0.66025 (15)	0.42940 (13)	0.16195 (9)	0.0236 (3)
H36	0.6049	0.4370	0.1969	0.028*
C37	0.50894 (14)	−0.12531 (12)	0.34997 (9)	0.0198 (3)
C38	0.49447 (16)	−0.19876 (13)	0.27965 (9)	0.0236 (3)
H38	0.5583	−0.1901	0.2499	0.028*
C39	0.38511 (17)	−0.28466 (14)	0.25394 (10)	0.0291 (4)
H39	0.3767	−0.3337	0.2059	0.035*
N40	0.29070 (14)	−0.30289 (12)	0.29235 (9)	0.0292 (3)
C41	0.30553 (15)	−0.23131 (13)	0.35940 (10)	0.0255 (3)
H41	0.2400	−0.2418	0.3878	0.031*
C42	0.41105 (15)	−0.14261 (13)	0.38984 (10)	0.0223 (3)
H42	0.4162	−0.0942	0.4376	0.027*
C43	0.98915 (15)	0.03021 (12)	0.72523 (9)	0.0204 (3)
C44	0.88414 (16)	0.01206 (13)	0.76040 (10)	0.0237 (3)
H44	0.7964	0.0292	0.7316	0.028*
C45	0.90891 (16)	−0.03093 (13)	0.83744 (10)	0.0252 (3)
H45	0.8365	−0.0428	0.8603	0.030*
N46	1.03012 (14)	−0.05665 (11)	0.88122 (8)	0.0262 (3)
C47	1.13159 (16)	−0.03645 (13)	0.84863 (10)	0.0248 (3)
H47	1.2186	−0.0524	0.8796	0.030*
C48	1.11569 (15)	0.00647 (13)	0.77213 (9)	0.0222 (3)
H48	1.1907	0.0197	0.7517	0.027*
O49	1.06478 (12)	−0.17504 (10)	0.01588 (7)	0.0305 (3)
H49	1.0476	−0.1262	−0.0371	0.050*
O50	0.84392 (12)	−0.17495 (11)	−0.01175 (7)	0.0335 (3)
C51	0.94991 (17)	−0.20741 (14)	0.02965 (10)	0.0273 (3)
C52	0.96124 (19)	−0.28598 (15)	0.09937 (11)	0.0344 (4)
H52A	0.8746	−0.2975	0.1108	0.052*
H52B	1.0292	−0.2483	0.1479	0.052*
H52C	0.9873	−0.3636	0.0850	0.052*
O53	0.65793 (12)	−0.42488 (12)	−0.10719 (8)	0.0370 (3)
H53	0.6837	−0.4714	−0.0555	0.050*
O54	0.87344 (13)	−0.43933 (12)	−0.09452 (8)	0.0400 (3)
C55	0.76760 (16)	−0.40384 (14)	−0.13013 (10)	0.0271 (3)
C56	0.74695 (19)	−0.33141 (17)	−0.20318 (11)	0.0373 (4)
H56A	0.7716	−0.2467	−0.1854	0.056*
H56B	0.6526	−0.3433	−0.2356	0.056*
H56C	0.8031	−0.3567	−0.2366	0.056*
O57	0.59433 (13)	−0.16264 (12)	−0.00994 (8)	0.0399 (3)
H57	0.6838	−0.1936	−0.0020	0.050*
O58	0.62972 (13)	−0.21511 (13)	0.11815 (8)	0.0417 (3)
C59	0.55699 (17)	−0.18052 (14)	0.05699 (10)	0.0287 (4)
C60	0.41659 (18)	−0.15168 (17)	0.04738 (12)	0.0371 (4)
H60A	0.3869	−0.1811	0.0931	0.056*
H60B	0.3574	−0.1901	−0.0041	0.056*
H60C	0.4135	−0.0649	0.0468	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0183 (7)	0.0202 (7)	0.0208 (7)	0.0013 (5)	0.0077 (6)	0.0021 (6)
C2	0.0214 (7)	0.0238 (7)	0.0196 (7)	−0.0001 (6)	0.0058 (6)	0.0017 (6)
C3	0.0205 (7)	0.0233 (7)	0.0203 (7)	−0.0013 (5)	0.0055 (6)	−0.0001 (6)
C4	0.0189 (7)	0.0179 (6)	0.0226 (7)	0.0013 (5)	0.0070 (6)	0.0011 (6)
C5	0.0183 (7)	0.0188 (6)	0.0213 (7)	0.0016 (5)	0.0071 (6)	0.0010 (6)
C6	0.0166 (7)	0.0188 (6)	0.0228 (7)	0.0016 (5)	0.0075 (6)	0.0016 (6)
C7	0.0200 (7)	0.0212 (7)	0.0237 (8)	−0.0015 (5)	0.0072 (6)	0.0036 (6)
C8	0.0214 (7)	0.0226 (7)	0.0235 (8)	−0.0006 (6)	0.0072 (6)	0.0048 (6)
C9	0.0177 (7)	0.0202 (7)	0.0212 (7)	0.0020 (5)	0.0061 (6)	0.0046 (6)
C10	0.0180 (7)	0.0216 (7)	0.0211 (7)	0.0016 (5)	0.0070 (6)	0.0024 (6)
C11	0.0205 (7)	0.0214 (7)	0.0197 (7)	0.0009 (5)	0.0071 (6)	0.0027 (6)
C12	0.0214 (8)	0.0257 (7)	0.0218 (8)	−0.0005 (6)	0.0045 (6)	0.0044 (6)
C13	0.0187 (7)	0.0242 (7)	0.0227 (8)	−0.0031 (5)	0.0037 (6)	0.0019 (6)
C14	0.0179 (7)	0.0202 (7)	0.0201 (7)	−0.0011 (5)	0.0064 (6)	−0.0002 (6)
C15	0.0180 (7)	0.0183 (6)	0.0203 (7)	0.0001 (5)	0.0076 (6)	0.0004 (5)
C16	0.0202 (7)	0.0184 (7)	0.0210 (7)	0.0016 (5)	0.0079 (6)	0.0008 (6)
C17	0.0222 (7)	0.0168 (6)	0.0242 (8)	−0.0003 (5)	0.0076 (6)	0.0016 (6)
C18	0.0221 (7)	0.0187 (7)	0.0222 (7)	0.0000 (5)	0.0074 (6)	0.0028 (6)
C19	0.0194 (7)	0.0203 (7)	0.0199 (7)	0.0015 (5)	0.0071 (6)	0.0023 (6)
C20	0.0190 (7)	0.0204 (7)	0.0196 (7)	0.0017 (5)	0.0062 (6)	0.0026 (6)
N21	0.0193 (6)	0.0195 (6)	0.0201 (6)	−0.0004 (5)	0.0067 (5)	0.0031 (5)
N22	0.0171 (6)	0.0201 (6)	0.0210 (6)	0.0003 (4)	0.0043 (5)	0.0019 (5)
N23	0.0186 (6)	0.0201 (6)	0.0193 (6)	−0.0020 (4)	0.0059 (5)	0.0020 (5)
N24	0.0191 (6)	0.0215 (6)	0.0195 (6)	0.0000 (5)	0.0054 (5)	0.0009 (5)
C25	0.0204 (7)	0.0214 (7)	0.0179 (7)	−0.0015 (5)	0.0079 (6)	0.0002 (6)
C26	0.0224 (8)	0.0219 (7)	0.0222 (7)	0.0019 (6)	0.0082 (6)	0.0011 (6)
C27	0.0290 (8)	0.0182 (7)	0.0267 (8)	−0.0008 (6)	0.0125 (7)	−0.0005 (6)
N28	0.0263 (7)	0.0242 (6)	0.0291 (7)	−0.0035 (5)	0.0086 (6)	−0.0013 (5)
C29	0.0215 (8)	0.0261 (8)	0.0313 (9)	−0.0003 (6)	0.0069 (7)	−0.0008 (7)
C30	0.0222 (8)	0.0197 (7)	0.0241 (8)	0.0002 (5)	0.0061 (6)	0.0002 (6)
C31	0.0208 (7)	0.0203 (7)	0.0207 (7)	−0.0037 (5)	0.0037 (6)	0.0022 (6)
C32	0.0222 (8)	0.0245 (7)	0.0242 (8)	0.0009 (6)	0.0075 (6)	0.0045 (6)
C33	0.0261 (8)	0.0284 (8)	0.0247 (8)	−0.0002 (6)	0.0092 (7)	0.0040 (6)
N34	0.0237 (7)	0.0309 (7)	0.0245 (7)	−0.0009 (5)	0.0061 (6)	0.0083 (6)
C35	0.0211 (8)	0.0293 (8)	0.0277 (8)	0.0021 (6)	0.0048 (6)	0.0063 (6)
C36	0.0196 (7)	0.0271 (7)	0.0235 (8)	0.0004 (6)	0.0055 (6)	0.0036 (6)
C37	0.0194 (7)	0.0171 (6)	0.0217 (7)	0.0009 (5)	0.0041 (6)	0.0040 (6)
C38	0.0257 (8)	0.0229 (7)	0.0217 (8)	−0.0006 (6)	0.0068 (6)	0.0029 (6)
C39	0.0328 (9)	0.0252 (8)	0.0250 (8)	−0.0035 (6)	0.0035 (7)	0.0000 (6)
N40	0.0257 (7)	0.0251 (7)	0.0324 (8)	−0.0025 (5)	0.0022 (6)	0.0059 (6)
C41	0.0212 (8)	0.0229 (7)	0.0326 (9)	0.0013 (6)	0.0074 (7)	0.0081 (6)
C42	0.0224 (8)	0.0193 (7)	0.0255 (8)	0.0024 (5)	0.0071 (6)	0.0044 (6)
C43	0.0254 (8)	0.0161 (6)	0.0201 (7)	−0.0003 (5)	0.0080 (6)	0.0007 (5)
C44	0.0243 (8)	0.0229 (7)	0.0246 (8)	0.0003 (6)	0.0086 (6)	0.0021 (6)
C45	0.0275 (8)	0.0253 (7)	0.0248 (8)	−0.0011 (6)	0.0118 (7)	0.0011 (6)
N46	0.0325 (8)	0.0241 (6)	0.0223 (7)	−0.0003 (5)	0.0094 (6)	0.0024 (5)
C47	0.0260 (8)	0.0250 (7)	0.0219 (8)	0.0030 (6)	0.0041 (6)	0.0023 (6)
C48	0.0220 (8)	0.0225 (7)	0.0231 (8)	0.0011 (6)	0.0083 (6)	0.0013 (6)
O49	0.0334 (7)	0.0343 (6)	0.0258 (6)	0.0016 (5)	0.0117 (5)	0.0069 (5)
O50	0.0334 (7)	0.0375 (7)	0.0309 (6)	0.0022 (5)	0.0121 (5)	0.0018 (5)
C51	0.0333 (9)	0.0261 (8)	0.0236 (8)	−0.0009 (6)	0.0115 (7)	−0.0033 (6)
C52	0.0437 (10)	0.0326 (9)	0.0280 (9)	−0.0041 (7)	0.0144 (8)	0.0018 (7)
O53	0.0230 (6)	0.0563 (8)	0.0325 (7)	0.0034 (5)	0.0074 (5)	0.0195 (6)
O54	0.0307 (7)	0.0502 (8)	0.0430 (8)	0.0104 (6)	0.0135 (6)	0.0136 (6)
C55	0.0271 (8)	0.0286 (8)	0.0242 (8)	−0.0010 (6)	0.0064 (7)	0.0013 (6)
C56	0.0382 (10)	0.0465 (10)	0.0268 (9)	−0.0013 (8)	0.0094 (8)	0.0083 (8)
O57	0.0374 (7)	0.0562 (8)	0.0289 (7)	0.0125 (6)	0.0106 (6)	0.0100 (6)
O58	0.0366 (7)	0.0603 (8)	0.0297 (7)	0.0109 (6)	0.0087 (6)	0.0122 (6)
C59	0.0330 (9)	0.0260 (8)	0.0253 (8)	−0.0003 (6)	0.0064 (7)	0.0009 (6)
C60	0.0320 (10)	0.0430 (10)	0.0356 (10)	0.0030 (7)	0.0085 (8)	0.0060 (8)

Geometric parameters (Å, º)

C1—N21	1.3733 (19)	C31—C32	1.391 (2)
C1—C20	1.405 (2)	C31—C36	1.395 (2)
C1—C2	1.436 (2)	C32—C33	1.379 (2)
C2—C3	1.356 (2)	C32—H32	0.9500
C2—H2	0.9500	C33—N34	1.341 (2)
C3—C4	1.435 (2)	C33—H33	0.9500
C3—H3	0.9500	N34—C35	1.341 (2)
C4—N21	1.3760 (18)	C35—C36	1.383 (2)
C4—C5	1.402 (2)	C35—H35	0.9500
C5—C6	1.412 (2)	C36—H36	0.9500
C5—C25	1.4969 (19)	C37—C42	1.389 (2)
C6—N22	1.3687 (18)	C37—C38	1.397 (2)
C6—C7	1.448 (2)	C38—C39	1.390 (2)
C7—C8	1.342 (2)	C38—H38	0.9500
C7—H7	0.9500	C39—N40	1.341 (2)
C8—C9	1.451 (2)	C39—H39	0.9500
C8—H8	0.9500	N40—C41	1.340 (2)
C9—N22	1.3697 (19)	C41—C42	1.390 (2)
C9—C10	1.406 (2)	C41—H41	0.9500
C10—C11	1.404 (2)	C42—H42	0.9500
C10—C31	1.491 (2)	C43—C48	1.393 (2)
C11—N23	1.3746 (19)	C43—C44	1.400 (2)
C11—C12	1.432 (2)	C44—C45	1.384 (2)
C12—C13	1.360 (2)	C44—H44	0.9500
C12—H12	0.9500	C45—N46	1.339 (2)
C13—C14	1.433 (2)	C45—H45	0.9500
C13—H13	0.9500	N46—C47	1.341 (2)
C14—N23	1.3731 (18)	C47—C48	1.383 (2)
C14—C15	1.407 (2)	C47—H47	0.9500
C15—C16	1.405 (2)	C48—H48	0.9500
C15—C37	1.4976 (19)	O49—C51	1.315 (2)
C16—N24	1.3778 (18)	O49—H49	1.0569
C16—C17	1.447 (2)	O50—C51	1.228 (2)
C17—C18	1.349 (2)	C51—C52	1.496 (2)
C17—H17	0.9500	C52—H52A	0.9800
C18—C19	1.4511 (19)	C52—H52B	0.9800
C18—H18	0.9500	C52—H52C	0.9800
C19—N24	1.3693 (19)	O53—C55	1.321 (2)
C19—C20	1.412 (2)	O53—H53	1.0264
C20—C43	1.490 (2)	O54—C55	1.211 (2)
N21—H21	0.9903	C55—C56	1.493 (2)
N23—H23	0.9872	C56—H56A	0.9800
C25—C30	1.392 (2)	C56—H56B	0.9800
C25—C26	1.396 (2)	C56—H56C	0.9800
C26—C27	1.387 (2)	O57—C59	1.328 (2)
C26—H26	0.9500	O57—H57	1.0020
C27—N28	1.334 (2)	O58—C59	1.206 (2)
C27—H27	0.9500	C59—C60	1.496 (2)
N28—C29	1.341 (2)	C60—H60A	0.9800
C29—C30	1.384 (2)	C60—H60B	0.9800
C29—H29	0.9500	C60—H60C	0.9800
C30—H30	0.9500
N21—C1—C20	125.59 (13)	C29—C30—C25	119.68 (14)
N21—C1—C2	108.00 (12)	C29—C30—H30	120.2
C20—C1—C2	126.40 (14)	C25—C30—H30	120.2
C3—C2—C1	107.54 (13)	C32—C31—C36	117.51 (14)
C3—C2—H2	126.2	C32—C31—C10	121.45 (13)
C1—C2—H2	126.2	C36—C31—C10	121.03 (13)
C2—C3—C4	108.06 (13)	C33—C32—C31	119.80 (14)
C2—C3—H3	126.0	C33—C32—H32	120.1
C4—C3—H3	126.0	C31—C32—H32	120.1
N21—C4—C5	126.60 (14)	N34—C33—C32	122.88 (14)
N21—C4—C3	107.68 (12)	N34—C33—H33	118.6
C5—C4—C3	125.70 (13)	C32—C33—H33	118.6
C4—C5—C6	124.98 (13)	C35—N34—C33	117.41 (14)
C4—C5—C25	117.12 (13)	N34—C35—C36	123.43 (15)
C6—C5—C25	117.88 (13)	N34—C35—H35	118.3
N22—C6—C5	125.25 (13)	C36—C35—H35	118.3
N22—C6—C7	109.70 (13)	C35—C36—C31	118.96 (14)
C5—C6—C7	124.98 (13)	C35—C36—H36	120.5
C8—C7—C6	107.33 (13)	C31—C36—H36	120.5
C8—C7—H7	126.3	C42—C37—C38	117.25 (13)
C6—C7—H7	126.3	C42—C37—C15	121.38 (13)
C7—C8—C9	106.76 (13)	C38—C37—C15	121.37 (13)
C7—C8—H8	126.6	C39—C38—C37	118.90 (14)
C9—C8—H8	126.6	C39—C38—H38	120.5
N22—C9—C10	125.86 (13)	C37—C38—H38	120.5
N22—C9—C8	109.88 (12)	N40—C39—C38	124.36 (15)
C10—C9—C8	124.19 (14)	N40—C39—H39	117.8
C11—C10—C9	126.01 (14)	C38—C39—H39	117.8
C11—C10—C31	116.89 (13)	C41—N40—C39	116.03 (13)
C9—C10—C31	117.10 (13)	N40—C41—C42	123.93 (15)
N23—C11—C10	125.76 (14)	N40—C41—H41	118.0
N23—C11—C12	108.14 (12)	C42—C41—H41	118.0
C10—C11—C12	126.00 (14)	C37—C42—C41	119.52 (14)
C13—C12—C11	107.49 (14)	C37—C42—H42	120.2
C13—C12—H12	126.3	C41—C42—H42	120.2
C11—C12—H12	126.3	C48—C43—C44	116.92 (14)
C12—C13—C14	107.92 (13)	C48—C43—C20	122.01 (13)
C12—C13—H13	126.0	C44—C43—C20	121.06 (14)
C14—C13—H13	126.0	C45—C44—C43	119.60 (15)
N23—C14—C15	125.54 (13)	C45—C44—H44	120.2
N23—C14—C13	107.88 (12)	C43—C44—H44	120.2
C15—C14—C13	126.58 (13)	N46—C45—C44	123.10 (14)
C16—C15—C14	125.39 (13)	N46—C45—H45	118.4
C16—C15—C37	118.26 (13)	C44—C45—H45	118.4
C14—C15—C37	116.34 (13)	C45—N46—C47	117.45 (14)
N24—C16—C15	125.61 (13)	N46—C47—C48	123.18 (15)
N24—C16—C17	109.52 (13)	N46—C47—H47	118.4
C15—C16—C17	124.85 (13)	C48—C47—H47	118.4
C18—C17—C16	107.30 (13)	C47—C48—C43	119.70 (14)
C18—C17—H17	126.4	C47—C48—H48	120.2
C16—C17—H17	126.4	C43—C48—H48	120.2
C17—C18—C19	106.86 (13)	C51—O49—H49	109.4
C17—C18—H18	126.6	O50—C51—O49	122.01 (15)
C19—C18—H18	126.6	O50—C51—C52	123.98 (15)
N24—C19—C20	125.57 (13)	O49—C51—C52	114.01 (15)
N24—C19—C18	109.86 (13)	C51—C52—H52A	109.5
C20—C19—C18	124.53 (14)	C51—C52—H52B	109.5
C1—C20—C19	125.43 (14)	H52A—C52—H52B	109.5
C1—C20—C43	117.30 (13)	C51—C52—H52C	109.5
C19—C20—C43	117.25 (13)	H52A—C52—H52C	109.5
C1—N21—C4	108.66 (12)	H52B—C52—H52C	109.5
C1—N21—H21	129.0	C55—O53—H53	106.8
C4—N21—H21	122.3	O54—C55—O53	122.81 (15)
C6—N22—C9	106.29 (12)	O54—C55—C56	124.22 (16)
C14—N23—C11	108.55 (12)	O53—C55—C56	112.96 (15)
C14—N23—H23	128.3	C55—C56—H56A	109.5
C11—N23—H23	123.0	C55—C56—H56B	109.5
C19—N24—C16	106.42 (12)	H56A—C56—H56B	109.5
C30—C25—C26	116.64 (13)	C55—C56—H56C	109.5
C30—C25—C5	120.78 (13)	H56A—C56—H56C	109.5
C26—C25—C5	122.57 (13)	H56B—C56—H56C	109.5
C27—C26—C25	119.20 (14)	C59—O57—H57	108.0
C27—C26—H26	120.4	O58—C59—O57	123.03 (16)
C25—C26—H26	120.4	O58—C59—C60	124.74 (16)
N28—C27—C26	124.58 (14)	O57—C59—C60	112.23 (15)
N28—C27—H27	117.7	C59—C60—H60A	109.5
C26—C27—H27	117.7	C59—C60—H60B	109.5
C27—N28—C29	115.72 (13)	H60A—C60—H60B	109.5
N28—C29—C30	124.14 (15)	C59—C60—H60C	109.5
N28—C29—H29	117.9	H60A—C60—H60C	109.5
C30—C29—H29	117.9	H60B—C60—H60C	109.5
N21—C1—C2—C3	−2.20 (16)	C10—C9—N22—C6	−175.58 (14)
C20—C1—C2—C3	177.84 (14)	C8—C9—N22—C6	1.30 (15)
C1—C2—C3—C4	0.88 (16)	C15—C14—N23—C11	179.03 (13)
C2—C3—C4—N21	0.74 (16)	C13—C14—N23—C11	−1.14 (15)
C2—C3—C4—C5	179.01 (14)	C10—C11—N23—C14	−175.74 (14)
N21—C4—C5—C6	7.6 (2)	C12—C11—N23—C14	0.88 (16)
C3—C4—C5—C6	−170.32 (14)	C20—C19—N24—C16	−175.69 (13)
N21—C4—C5—C25	−170.92 (13)	C18—C19—N24—C16	2.09 (15)
C3—C4—C5—C25	11.1 (2)	C15—C16—N24—C19	176.53 (13)
C4—C5—C6—N22	0.6 (2)	C17—C16—N24—C19	−1.80 (15)
C25—C5—C6—N22	179.16 (12)	C4—C5—C25—C30	54.85 (18)
C4—C5—C6—C7	177.57 (13)	C6—C5—C25—C30	−123.79 (15)
C25—C5—C6—C7	−3.9 (2)	C4—C5—C25—C26	−126.11 (15)
N22—C6—C7—C8	2.07 (16)	C6—C5—C25—C26	55.26 (19)
C5—C6—C7—C8	−175.26 (14)	C30—C25—C26—C27	1.9 (2)
C6—C7—C8—C9	−1.20 (16)	C5—C25—C26—C27	−177.15 (13)
C7—C8—C9—N22	−0.03 (17)	C25—C26—C27—N28	−1.0 (2)
C7—C8—C9—C10	176.92 (14)	C26—C27—N28—C29	−0.8 (2)
N22—C9—C10—C11	−3.9 (2)	C27—N28—C29—C30	1.8 (2)
C8—C9—C10—C11	179.64 (14)	N28—C29—C30—C25	−0.9 (2)
N22—C9—C10—C31	176.06 (13)	C26—C25—C30—C29	−1.1 (2)
C8—C9—C10—C31	−0.4 (2)	C5—C25—C30—C29	178.05 (14)
C9—C10—C11—N23	−4.4 (2)	C11—C10—C31—C32	−113.70 (16)
C31—C10—C11—N23	175.68 (13)	C9—C10—C31—C32	66.32 (18)
C9—C10—C11—C12	179.62 (14)	C11—C10—C31—C36	67.61 (18)
C31—C10—C11—C12	−0.3 (2)	C9—C10—C31—C36	−112.36 (16)
N23—C11—C12—C13	−0.25 (17)	C36—C31—C32—C33	0.1 (2)
C10—C11—C12—C13	176.35 (14)	C10—C31—C32—C33	−178.62 (13)
C11—C12—C13—C14	−0.44 (17)	C31—C32—C33—N34	−0.1 (2)
C12—C13—C14—N23	0.99 (17)	C32—C33—N34—C35	0.5 (2)
C12—C13—C14—C15	−179.19 (14)	C33—N34—C35—C36	−1.0 (2)
N23—C14—C15—C16	5.4 (2)	N34—C35—C36—C31	1.1 (2)
C13—C14—C15—C16	−174.40 (14)	C32—C31—C36—C35	−0.6 (2)
N23—C14—C15—C37	−176.07 (13)	C10—C31—C36—C35	178.16 (13)
C13—C14—C15—C37	4.1 (2)	C16—C15—C37—C42	58.34 (19)
C14—C15—C16—N24	4.1 (2)	C14—C15—C37—C42	−120.30 (15)
C37—C15—C16—N24	−174.45 (13)	C16—C15—C37—C38	−121.78 (15)
C14—C15—C16—C17	−177.87 (13)	C14—C15—C37—C38	59.58 (19)
C37—C15—C16—C17	3.6 (2)	C42—C37—C38—C39	−0.5 (2)
N24—C16—C17—C18	0.82 (16)	C15—C37—C38—C39	179.63 (14)
C15—C16—C17—C18	−177.52 (13)	C37—C38—C39—N40	−0.1 (3)
C16—C17—C18—C19	0.46 (16)	C38—C39—N40—C41	0.5 (2)
C17—C18—C19—N24	−1.61 (16)	C39—N40—C41—C42	−0.3 (2)
C17—C18—C19—C20	176.19 (14)	C38—C37—C42—C41	0.7 (2)
N21—C1—C20—C19	−3.8 (2)	C15—C37—C42—C41	−179.41 (13)
C2—C1—C20—C19	176.13 (14)	N40—C41—C42—C37	−0.3 (2)
N21—C1—C20—C43	177.70 (13)	C1—C20—C43—C48	−54.04 (19)
C2—C1—C20—C43	−2.4 (2)	C19—C20—C43—C48	127.35 (15)
N24—C19—C20—C1	−9.1 (2)	C1—C20—C43—C44	125.35 (15)
C18—C19—C20—C1	173.43 (14)	C19—C20—C43—C44	−53.26 (19)
N24—C19—C20—C43	169.38 (13)	C48—C43—C44—C45	−1.8 (2)
C18—C19—C20—C43	−8.1 (2)	C20—C43—C44—C45	178.76 (13)
C20—C1—N21—C4	−177.37 (13)	C43—C44—C45—N46	0.0 (2)
C2—C1—N21—C4	2.68 (15)	C44—C45—N46—C47	1.6 (2)
C5—C4—N21—C1	179.62 (13)	C45—N46—C47—C48	−1.5 (2)
C3—C4—N21—C1	−2.14 (15)	N46—C47—C48—C43	−0.3 (2)
C5—C6—N22—C9	175.29 (13)	C44—C43—C48—C47	1.9 (2)
C7—C6—N22—C9	−2.04 (15)	C20—C43—C48—C47	−178.67 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O49—H49···N46^i	1.06	1.60	2.6572 (17)	176
O53—H53···N34^ii	1.03	1.66	2.6733 (18)	167
O57—H57···O50	1.00	1.73	2.6367 (18)	149

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