2,8,14,20-Tetra­phenyl­pyrogallol[4]arene dimethyl­formamide octa­solvate

Kass, J.P.; Zambrano, C.H.; Zeller, M.; Hunter, A.D.; Dueno, E.E.

doi:10.1107/S160053680602469X

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2,8,14,20-Tetraphenylpyrogallol[4]arene dimethylformamide octasolvate

J. P. Kass, C. H. Zambrano, M. Zeller, A. D. Hunter and E. E. Dueno

The title compound, C₅₂H₄₀O₁₂·8C₃H₇NO, contains substituted pyrogallolarene molecules accompanied by dimethylformamide solvent molecules. The complete main molecule displays a chair structure and has inversion symmetry. A network of O—H

O hydrogen bonds helps to consolidate the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602469X/hb2095sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680602469X/hb2095Isup2.hkl Contains datablock I

CCDC reference: 610181

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.058
wR factor = 0.169
Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.768     1.000
            Tmin(prime) and Tmax expected:      0.953     0.993
            RR(prime) =      0.801
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.80
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      20.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

   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

   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,8,14,20-Tetraphenylpyrogallol[4]arene dimethylformamide octasolvate top

Crystal data top

C₅₂H₄₀O₁₂·8C₃H₇NO	Z = 1
M_r = 1441.61	F(000) = 768
Triclinic, P1	D_x = 1.307 Mg m⁻³
Hall symbol: -P 1	Melting point: 632 K
a = 12.199 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.397 (4) Å	Cell parameters from 8495 reflections
c = 13.712 (4) Å	θ = 2.6–30.6°
α = 105.282 (5)°	µ = 0.10 mm⁻¹
β = 101.099 (5)°	T = 100 K
γ = 106.854 (5)°	Plate, colourless
V = 1831.5 (9) Å³	0.5 × 0.4 × 0.07 mm

Data collection top

Bruker SMART APEX CCD diffractometer	8997 independent reflections
Radiation source: fine-focus sealed tube	5924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2002)	h = −16→16
T_min = 0.768, T_max = 1	k = −16→16
18122 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.169	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0871P)² + 0.3671P] where P = (F_o² + 2F_c²)/3
8997 reflections	(Δ/σ)_max < 0.001
501 parameters	Δρ_max = 0.48 e Å⁻³
26 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.31161 (14)	−0.04065 (14)	0.60839 (14)	0.0333 (4)
N1	0.25617 (16)	0.12137 (17)	0.64951 (15)	0.0254 (4)
C1	0.33408 (19)	0.0673 (2)	0.65680 (18)	0.0273 (5)
H1	0.4129	0.1137	0.7021	0.033*
C2	0.1351 (2)	0.0559 (2)	0.5769 (2)	0.0339 (6)
H2C	0.1387	0.0385	0.5038	0.051*
H2D	0.0855	0.1049	0.5891	0.051*
H2E	0.1000	−0.0194	0.5891	0.051*
C3	0.2873 (2)	0.2479 (2)	0.70856 (19)	0.0289 (5)
H3C	0.3732	0.2839	0.7456	0.043*
H3D	0.2419	0.2557	0.7601	0.043*
H3E	0.2676	0.2892	0.6596	0.043*
O2	0.3715 (3)	0.2357 (4)	0.4735 (4)	0.0340 (8)	0.863 (3)
C4	0.3017 (3)	0.2879 (3)	0.4568 (2)	0.0286 (6)	0.863 (3)
H4	0.2300	0.2649	0.4762	0.034*	0.863 (3)
N2	0.3185 (2)	0.3742 (2)	0.41351 (19)	0.0303 (6)	0.863 (3)
C5	0.2340 (3)	0.4366 (3)	0.4046 (3)	0.0385 (8)	0.863 (3)
H5C	0.1650	0.3985	0.4263	0.058*	0.863 (3)
H5D	0.2069	0.4324	0.3312	0.058*	0.863 (3)
H5E	0.2735	0.5207	0.4504	0.058*	0.863 (3)
C6	0.4232 (3)	0.4124 (3)	0.3775 (3)	0.0414 (8)	0.863 (3)
H6A	0.4823	0.3801	0.4046	0.062*	0.863 (3)
H6B	0.4584	0.5001	0.4035	0.062*	0.863 (3)
H6C	0.3995	0.3826	0.3000	0.062*	0.863 (3)
O2C	0.346 (3)	0.226 (3)	0.483 (3)	0.0340 (8)	0.137 (3)
C4C	0.3427 (17)	0.2992 (18)	0.4379 (17)	0.0286 (6)	0.137 (3)
H4C	0.4020	0.3192	0.4033	0.034*	0.137 (3)
N2C	0.2618 (13)	0.3525 (13)	0.4335 (12)	0.0303 (6)	0.137 (3)
C5C	0.278 (2)	0.453 (2)	0.396 (2)	0.0385 (8)	0.137 (3)
H5C1	0.3564	0.4762	0.3839	0.058*	0.137 (3)
H5C2	0.2731	0.5202	0.4498	0.058*	0.137 (3)
H5C3	0.2149	0.4300	0.3304	0.058*	0.137 (3)
C6C	0.1593 (14)	0.3203 (18)	0.4742 (15)	0.0414 (8)	0.137 (3)
H6C1	0.1419	0.2387	0.4763	0.062*	0.137 (3)
H6C2	0.0894	0.3239	0.4280	0.062*	0.137 (3)
H6C3	0.1779	0.3765	0.5457	0.062*	0.137 (3)
O3	0.74920 (14)	0.90029 (14)	0.89433 (13)	0.0282 (4)
N3	0.67255 (15)	0.96148 (16)	0.76250 (14)	0.0227 (4)
C7	0.76129 (19)	0.96283 (19)	0.83541 (17)	0.0230 (4)
H7	0.8398	1.0146	0.8441	0.028*
C8	0.54917 (19)	0.8842 (2)	0.74269 (19)	0.0297 (5)
H8A	0.5196	0.8268	0.6704	0.045*
H8B	0.4991	0.9332	0.7514	0.045*
H8C	0.5458	0.8408	0.7930	0.045*
C9	0.6923 (2)	1.0345 (2)	0.69487 (19)	0.0297 (5)
H9A	0.7775	1.0835	0.7154	0.045*
H9B	0.6456	1.0869	0.7029	0.045*
H9C	0.6670	0.9821	0.6210	0.045*
O4	−0.02849 (16)	0.91253 (15)	0.72569 (14)	0.0369 (4)
N4	0.08930 (17)	0.84605 (17)	0.82835 (16)	0.0279 (4)
C10	−0.0153 (2)	0.8451 (2)	0.77530 (19)	0.0292 (5)
H10	−0.0858	0.7872	0.7758	0.035*
C11	0.2020 (2)	0.9313 (2)	0.8325 (2)	0.0362 (6)
H11A	0.1864	0.9800	0.7895	0.054*
H11B	0.2513	0.8879	0.8050	0.054*
H11C	0.2444	0.9834	0.9059	0.054*
C12	0.0940 (2)	0.7637 (2)	0.8862 (2)	0.0334 (5)
H12A	0.1253	0.8087	0.9622	0.050*
H12B	0.1466	0.7213	0.8648	0.050*
H12C	0.0133	0.7055	0.8705	0.050*
C1A	0.66115 (19)	0.25181 (19)	0.91647 (17)	0.0243 (4)
H1A1	0.7288	0.2446	0.8946	0.029*
C2A	0.5985 (2)	0.1667 (2)	0.95465 (19)	0.0306 (5)
H2A1	0.6243	0.1024	0.9593	0.037*
C3A	0.4998 (2)	0.1754 (2)	0.98562 (19)	0.0345 (6)
H3A1	0.4573	0.1171	1.0113	0.041*
C4A	0.4623 (2)	0.2699 (2)	0.9792 (2)	0.0378 (6)
H4A	0.3942	0.2763	1.0006	0.045*
C5A	0.52493 (19)	0.3549 (2)	0.94137 (19)	0.0296 (5)
H5A	0.4987	0.4189	0.9368	0.035*
C6A	0.62514 (17)	0.34758 (19)	0.91011 (16)	0.0204 (4)
C7A	0.69330 (17)	0.44472 (17)	0.87167 (16)	0.0177 (4)
H7A	0.6328	0.4737	0.8378	0.021*
C8A	0.74507 (17)	0.39330 (17)	0.78589 (16)	0.0169 (4)
C9A	0.66703 (16)	0.32301 (17)	0.68478 (16)	0.0172 (4)
C10A	0.70693 (17)	0.26725 (17)	0.60476 (16)	0.0179 (4)
C11A	0.82808 (17)	0.28056 (17)	0.62340 (15)	0.0165 (4)
C12A	0.90828 (16)	0.35043 (17)	0.72367 (16)	0.0168 (4)
C13A	0.86555 (17)	0.40571 (17)	0.80272 (16)	0.0171 (4)
H13A	0.9204	0.4535	0.8705	0.021*
C1B	1.23977 (18)	0.51700 (19)	0.75398 (17)	0.0219 (4)
H1B1	1.2799	0.4829	0.7968	0.026*
C2B	1.3062 (2)	0.6099 (2)	0.72625 (18)	0.0276 (5)
H2B1	1.3912	0.6391	0.7510	0.033*
C3B	1.2499 (2)	0.6601 (2)	0.66308 (19)	0.0299 (5)
H3B1	1.2957	0.7234	0.6443	0.036*
C4B	1.1258 (2)	0.6171 (2)	0.62755 (19)	0.0288 (5)
H4B	1.0863	0.6507	0.5838	0.035*
C5B	1.05914 (19)	0.5250 (2)	0.65568 (18)	0.0244 (5)
H5B	0.9742	0.4966	0.6310	0.029*
C6B	1.11444 (17)	0.47313 (18)	0.71952 (16)	0.0186 (4)
C7B	1.04044 (16)	0.36534 (17)	0.74297 (15)	0.0165 (4)
H7B	1.0418	0.2932	0.6898	0.020*
C8B	1.09230 (16)	0.35832 (17)	0.85051 (15)	0.0164 (4)
C9B	1.06900 (16)	0.24441 (17)	0.85955 (16)	0.0176 (4)
C10B	1.11424 (17)	0.23081 (18)	0.95522 (17)	0.0190 (4)
C11B	1.18962 (17)	0.33193 (18)	1.04200 (16)	0.0190 (4)
C12B	1.21629 (17)	0.44726 (18)	1.03517 (16)	0.0179 (4)
C13B	1.16358 (17)	0.45734 (18)	0.93973 (16)	0.0180 (4)
H13B	1.1769	0.5352	0.9355	0.022*
O1A	0.54856 (12)	0.30995 (14)	0.66641 (12)	0.0223 (3)
H1A	0.5127	0.2738	0.6018	0.033*
O2A	0.62121 (12)	0.20383 (14)	0.50824 (11)	0.0232 (3)
H2A	0.6411	0.1496	0.4738	0.035*
O3A	0.87216 (12)	0.22918 (13)	0.54627 (11)	0.0216 (3)
H3A	0.8160	0.1714	0.4986	0.032*
O1B	1.00058 (13)	0.14664 (13)	0.77173 (12)	0.0223 (3)
H1B	1.0080	0.0846	0.7814	0.033*
O2B	1.07824 (13)	0.11569 (13)	0.95740 (12)	0.0254 (3)
H2B	1.1297	0.1102	1.0044	0.038*
O3B	1.23926 (14)	0.32294 (14)	1.13777 (11)	0.0248 (3)
H3B	1.2480	0.2565	1.1273	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0238 (8)	0.0261 (9)	0.0415 (10)	0.0084 (7)	0.0040 (7)	0.0026 (7)
N1	0.0164 (8)	0.0255 (10)	0.0289 (10)	0.0052 (7)	0.0048 (7)	0.0048 (8)
C1	0.0174 (10)	0.0273 (12)	0.0315 (12)	0.0054 (9)	0.0065 (9)	0.0046 (9)
C2	0.0197 (11)	0.0335 (13)	0.0387 (13)	0.0081 (10)	0.0004 (10)	0.0044 (11)
C3	0.0229 (11)	0.0270 (12)	0.0345 (13)	0.0079 (9)	0.0100 (10)	0.0068 (10)
O2	0.032 (2)	0.0377 (13)	0.0331 (15)	0.0185 (16)	0.0002 (13)	0.0127 (9)
C4	0.0236 (16)	0.0346 (14)	0.0288 (15)	0.0113 (13)	0.0057 (11)	0.0133 (11)
N2	0.0261 (13)	0.0292 (12)	0.0349 (13)	0.0098 (11)	0.0047 (10)	0.0130 (10)
C5	0.042 (2)	0.0393 (17)	0.0422 (17)	0.0238 (18)	0.0086 (18)	0.0183 (13)
C6	0.0291 (15)	0.0458 (18)	0.0372 (16)	0.0013 (13)	0.0001 (12)	0.0155 (14)
O2C	0.032 (2)	0.0377 (13)	0.0331 (15)	0.0185 (16)	0.0002 (13)	0.0127 (9)
C4C	0.0236 (16)	0.0346 (14)	0.0288 (15)	0.0113 (13)	0.0057 (11)	0.0133 (11)
N2C	0.0261 (13)	0.0292 (12)	0.0349 (13)	0.0098 (11)	0.0047 (10)	0.0130 (10)
C5C	0.042 (2)	0.0393 (17)	0.0422 (17)	0.0238 (18)	0.0086 (18)	0.0183 (13)
C6C	0.0291 (15)	0.0458 (18)	0.0372 (16)	0.0013 (13)	0.0001 (12)	0.0155 (14)
O3	0.0260 (8)	0.0304 (8)	0.0328 (9)	0.0112 (7)	0.0058 (7)	0.0190 (7)
N3	0.0176 (8)	0.0233 (9)	0.0283 (9)	0.0055 (7)	0.0047 (7)	0.0141 (8)
C7	0.0171 (10)	0.0237 (11)	0.0288 (11)	0.0067 (8)	0.0052 (8)	0.0117 (9)
C8	0.0184 (10)	0.0338 (13)	0.0349 (13)	0.0040 (9)	0.0039 (9)	0.0172 (10)
C9	0.0291 (12)	0.0292 (12)	0.0350 (13)	0.0090 (10)	0.0079 (10)	0.0201 (10)
O4	0.0376 (10)	0.0250 (9)	0.0453 (10)	0.0112 (7)	0.0043 (8)	0.0133 (8)
N4	0.0237 (9)	0.0256 (10)	0.0374 (11)	0.0089 (8)	0.0103 (8)	0.0147 (8)
C10	0.0255 (11)	0.0216 (11)	0.0384 (13)	0.0076 (9)	0.0073 (10)	0.0095 (10)
C11	0.0234 (11)	0.0357 (14)	0.0488 (15)	0.0068 (10)	0.0121 (11)	0.0163 (12)
C12	0.0345 (13)	0.0324 (13)	0.0397 (14)	0.0155 (11)	0.0118 (11)	0.0178 (11)
C1A	0.0184 (10)	0.0257 (11)	0.0270 (11)	0.0043 (8)	0.0065 (8)	0.0103 (9)
C2A	0.0290 (12)	0.0269 (12)	0.0319 (12)	0.0028 (10)	0.0063 (10)	0.0135 (10)
C3A	0.0273 (12)	0.0354 (13)	0.0306 (13)	−0.0048 (10)	0.0088 (10)	0.0128 (10)
C4A	0.0221 (11)	0.0454 (15)	0.0407 (14)	0.0019 (11)	0.0175 (11)	0.0117 (12)
C5A	0.0192 (11)	0.0319 (12)	0.0354 (13)	0.0073 (9)	0.0103 (9)	0.0085 (10)
C6A	0.0125 (9)	0.0240 (10)	0.0196 (10)	0.0014 (8)	0.0028 (7)	0.0061 (8)
C7A	0.0134 (9)	0.0186 (10)	0.0207 (10)	0.0060 (7)	0.0038 (7)	0.0066 (8)
C8A	0.0148 (9)	0.0158 (9)	0.0217 (10)	0.0053 (7)	0.0057 (8)	0.0088 (8)
C9A	0.0108 (9)	0.0184 (10)	0.0238 (10)	0.0039 (7)	0.0046 (7)	0.0112 (8)
C10A	0.0147 (9)	0.0169 (9)	0.0207 (10)	0.0028 (7)	0.0025 (7)	0.0092 (8)
C11A	0.0143 (9)	0.0161 (9)	0.0207 (10)	0.0037 (7)	0.0057 (7)	0.0105 (8)
C12A	0.0122 (9)	0.0175 (9)	0.0230 (10)	0.0040 (7)	0.0050 (7)	0.0118 (8)
C13A	0.0127 (9)	0.0164 (9)	0.0205 (10)	0.0023 (7)	0.0029 (7)	0.0081 (8)
C1B	0.0160 (10)	0.0229 (11)	0.0282 (11)	0.0061 (8)	0.0072 (8)	0.0112 (9)
C2B	0.0181 (10)	0.0285 (12)	0.0336 (12)	0.0020 (9)	0.0093 (9)	0.0123 (10)
C3B	0.0281 (12)	0.0278 (12)	0.0332 (12)	0.0024 (9)	0.0120 (10)	0.0160 (10)
C4B	0.0275 (11)	0.0281 (12)	0.0333 (12)	0.0068 (9)	0.0068 (10)	0.0195 (10)
C5B	0.0176 (10)	0.0272 (11)	0.0300 (11)	0.0054 (8)	0.0065 (8)	0.0158 (9)
C6B	0.0155 (9)	0.0195 (10)	0.0231 (10)	0.0054 (8)	0.0087 (8)	0.0094 (8)
C7B	0.0125 (9)	0.0169 (9)	0.0204 (9)	0.0040 (7)	0.0033 (7)	0.0094 (8)
C8B	0.0104 (8)	0.0199 (10)	0.0218 (10)	0.0064 (7)	0.0055 (7)	0.0102 (8)
C9B	0.0099 (8)	0.0182 (10)	0.0250 (10)	0.0042 (7)	0.0053 (7)	0.0084 (8)
C10B	0.0138 (9)	0.0182 (10)	0.0279 (11)	0.0059 (8)	0.0071 (8)	0.0114 (8)
C11B	0.0132 (9)	0.0246 (10)	0.0226 (10)	0.0080 (8)	0.0054 (8)	0.0119 (8)
C12B	0.0122 (9)	0.0200 (10)	0.0223 (10)	0.0063 (7)	0.0058 (8)	0.0073 (8)
C13B	0.0135 (9)	0.0187 (10)	0.0251 (10)	0.0069 (7)	0.0075 (8)	0.0102 (8)
O1A	0.0111 (6)	0.0296 (8)	0.0230 (7)	0.0059 (6)	0.0020 (5)	0.0077 (6)
O2A	0.0161 (7)	0.0278 (8)	0.0211 (7)	0.0075 (6)	0.0016 (6)	0.0044 (6)
O3A	0.0159 (7)	0.0246 (8)	0.0215 (7)	0.0050 (6)	0.0055 (6)	0.0058 (6)
O1B	0.0191 (7)	0.0167 (7)	0.0279 (8)	0.0035 (6)	0.0014 (6)	0.0099 (6)
O2B	0.0227 (8)	0.0205 (7)	0.0314 (9)	0.0045 (6)	0.0011 (6)	0.0146 (7)
O3B	0.0249 (8)	0.0259 (8)	0.0244 (8)	0.0091 (7)	0.0023 (6)	0.0136 (6)

Geometric parameters (Å, º) top

O1—C1	1.248 (3)	C1A—C6A	1.397 (3)
N1—C1	1.315 (3)	C1A—H1A1	0.9500
N1—C3	1.459 (3)	C2A—C3A	1.375 (4)
N1—C2	1.465 (3)	C2A—H2A1	0.9500
C1—H1	0.9500	C3A—C4A	1.392 (4)
C2—H2C	0.9800	C3A—H3A1	0.9500
C2—H2D	0.9800	C4A—C5A	1.392 (3)
C2—H2E	0.9800	C4A—H4A	0.9500
C3—H3C	0.9800	C5A—C6A	1.390 (3)
C3—H3D	0.9800	C5A—H5A	0.9500
C3—H3E	0.9800	C6A—C7A	1.530 (3)
O2—C4	1.232 (4)	C7A—C8A	1.521 (3)
C4—N2	1.339 (3)	C7A—C12Bⁱ	1.530 (3)
C4—H4	0.9500	C7A—H7A	1.0000
N2—C6	1.455 (4)	C8A—C13A	1.399 (3)
N2—C5	1.463 (4)	C8A—C9A	1.401 (3)
C5—H5C	0.9800	C9A—O1A	1.372 (2)
C5—H5D	0.9800	C9A—C10A	1.385 (3)
C5—H5E	0.9800	C10A—O2A	1.380 (2)
C6—H6A	0.9800	C10A—C11A	1.403 (3)
C6—H6B	0.9800	C11A—O3A	1.370 (2)
C6—H6C	0.9800	C11A—C12A	1.400 (3)
O2C—C4C	1.234 (17)	C12A—C13A	1.396 (3)
C4C—N2C	1.338 (15)	C12A—C7B	1.530 (3)
C4C—H4C	0.9500	C13A—H13A	0.9500
N2C—C5C	1.438 (16)	C1B—C2B	1.391 (3)
N2C—C6C	1.459 (15)	C1B—C6B	1.400 (3)
C5C—H5C1	0.9800	C1B—H1B1	0.9500
C5C—H5C2	0.9800	C2B—C3B	1.384 (3)
C5C—H5C3	0.9800	C2B—H2B1	0.9500
C6C—H6C1	0.9800	C3B—C4B	1.387 (3)
C6C—H6C2	0.9800	C3B—H3B1	0.9500
C6C—H6C3	0.9800	C4B—C5B	1.389 (3)
O3—C7	1.259 (3)	C4B—H4B	0.9500
N3—C7	1.317 (3)	C5B—C6B	1.398 (3)
N3—C8	1.458 (3)	C5B—H5B	0.9500
N3—C9	1.463 (3)	C6B—C7B	1.531 (3)
C7—H7	0.9500	C7B—C8B	1.524 (3)
C8—H8A	0.9800	C7B—H7B	1.0000
C8—H8B	0.9800	C8B—C13B	1.393 (3)
C8—H8C	0.9800	C8B—C9B	1.401 (3)
C9—H9A	0.9800	C9B—O1B	1.369 (2)
C9—H9B	0.9800	C9B—C10B	1.395 (3)
C9—H9C	0.9800	C10B—O2B	1.377 (2)
O4—C10	1.235 (3)	C10B—C11B	1.399 (3)
N4—C10	1.336 (3)	C11B—O3B	1.383 (2)
N4—C11	1.451 (3)	C11B—C12B	1.404 (3)
N4—C12	1.456 (3)	C12B—C13B	1.397 (3)
C10—H10	0.9500	C12B—C7Aⁱ	1.530 (3)
C11—H11A	0.9800	C13B—H13B	0.9500
C11—H11B	0.9800	O1A—H1A	0.8400
C11—H11C	0.9800	O2A—H2A	0.8400
C12—H12A	0.9800	O3A—H3A	0.8400
C12—H12B	0.9800	O1B—H1B	0.8400
C12—H12C	0.9800	O2B—H2B	0.8400
C1A—C2A	1.396 (3)	O3B—H3B	0.8400

C1—N1—C3	122.19 (19)	C5A—C6A—C1A	118.4 (2)
C1—N1—C2	120.15 (19)	C5A—C6A—C7A	119.42 (19)
C3—N1—C2	117.61 (18)	C1A—C6A—C7A	122.20 (18)
O1—C1—N1	124.5 (2)	C8A—C7A—C12Bⁱ	114.82 (16)
O1—C1—H1	117.7	C8A—C7A—C6A	111.36 (16)
N1—C1—H1	117.7	C12Bⁱ—C7A—C6A	110.94 (16)
N1—C2—H2C	109.5	C8A—C7A—H7A	106.4
N1—C2—H2D	109.5	C12Bⁱ—C7A—H7A	106.4
H2C—C2—H2D	109.5	C6A—C7A—H7A	106.4
N1—C2—H2E	109.5	C13A—C8A—C9A	117.21 (18)
H2C—C2—H2E	109.5	C13A—C8A—C7A	124.12 (17)
H2D—C2—H2E	109.5	C9A—C8A—C7A	118.56 (17)
N1—C3—H3C	109.5	O1A—C9A—C10A	120.22 (17)
N1—C3—H3D	109.5	O1A—C9A—C8A	118.19 (17)
H3C—C3—H3D	109.5	C10A—C9A—C8A	121.59 (17)
N1—C3—H3E	109.5	O2A—C10A—C9A	115.48 (17)
H3C—C3—H3E	109.5	O2A—C10A—C11A	124.19 (18)
H3D—C3—H3E	109.5	C9A—C10A—C11A	120.29 (18)
O2—C4—N2	125.5 (3)	O3A—C11A—C12A	118.16 (16)
O2—C4—H4	117.3	O3A—C11A—C10A	122.41 (17)
N2—C4—H4	117.3	C12A—C11A—C10A	119.42 (18)
C4—N2—C6	121.4 (3)	C13A—C12A—C11A	119.02 (17)
C4—N2—C5	120.9 (3)	C13A—C12A—C7B	121.93 (17)
C6—N2—C5	117.6 (3)	C11A—C12A—C7B	119.04 (17)
O2C—C4C—N2C	125 (2)	C12A—C13A—C8A	122.47 (18)
O2C—C4C—H4C	117.5	C12A—C13A—H13A	118.8
N2C—C4C—H4C	117.5	C8A—C13A—H13A	118.8
C4C—N2C—C5C	121.0 (16)	C2B—C1B—C6B	120.78 (19)
C4C—N2C—C6C	122.5 (14)	C2B—C1B—H1B1	119.6
C5C—N2C—C6C	116.3 (15)	C6B—C1B—H1B1	119.6
N2C—C5C—H5C1	109.5	C3B—C2B—C1B	120.7 (2)
N2C—C5C—H5C2	109.5	C3B—C2B—H2B1	119.7
H5C1—C5C—H5C2	109.5	C1B—C2B—H2B1	119.7
N2C—C5C—H5C3	109.5	C2B—C3B—C4B	119.3 (2)
H5C1—C5C—H5C3	109.5	C2B—C3B—H3B1	120.4
H5C2—C5C—H5C3	109.5	C4B—C3B—H3B1	120.4
N2C—C6C—H6C1	109.5	C3B—C4B—C5B	120.2 (2)
N2C—C6C—H6C2	109.5	C3B—C4B—H4B	119.9
H6C1—C6C—H6C2	109.5	C5B—C4B—H4B	119.9
N2C—C6C—H6C3	109.5	C4B—C5B—C6B	121.3 (2)
H6C1—C6C—H6C3	109.5	C4B—C5B—H5B	119.3
H6C2—C6C—H6C3	109.5	C6B—C5B—H5B	119.3
C7—N3—C8	121.69 (18)	C5B—C6B—C1B	117.68 (18)
C7—N3—C9	122.10 (18)	C5B—C6B—C7B	120.86 (17)
C8—N3—C9	116.18 (17)	C1B—C6B—C7B	121.26 (17)
O3—C7—N3	124.5 (2)	C8B—C7B—C12A	111.25 (16)
O3—C7—H7	117.7	C8B—C7B—C6B	114.99 (16)
N3—C7—H7	117.7	C12A—C7B—C6B	113.15 (15)
C10—N4—C11	121.2 (2)	C8B—C7B—H7B	105.5
C10—N4—C12	121.1 (2)	C12A—C7B—H7B	105.5
C11—N4—C12	117.7 (2)	C6B—C7B—H7B	105.5
O4—C10—N4	125.9 (2)	C13B—C8B—C9B	117.82 (17)
O4—C10—H10	117.0	C13B—C8B—C7B	124.39 (17)
N4—C10—H10	117.0	C9B—C8B—C7B	117.77 (17)
C2A—C1A—C6A	120.5 (2)	O1B—C9B—C10B	120.84 (18)
C2A—C1A—H1A1	119.7	O1B—C9B—C8B	118.11 (17)
C6A—C1A—H1A1	119.7	C10B—C9B—C8B	121.05 (18)
C3A—C2A—C1A	120.4 (2)	O2B—C10B—C9B	116.17 (18)
C3A—C2A—H2A1	119.8	O2B—C10B—C11B	124.26 (18)
C1A—C2A—H2A1	119.8	C9B—C10B—C11B	119.55 (18)
C2A—C3A—C4A	119.8 (2)	O3B—C11B—C10B	121.78 (18)
C2A—C3A—H3A1	120.1	O3B—C11B—C12B	117.43 (18)
C4A—C3A—H3A1	120.1	C10B—C11B—C12B	120.78 (18)
C3A—C4A—C5A	119.8 (2)	C13B—C12B—C11B	117.77 (18)
C3A—C4A—H4A	120.1	C13B—C12B—C7Aⁱ	122.50 (18)
C5A—C4A—H4A	120.1	C11B—C12B—C7Aⁱ	119.62 (17)
C6A—C5A—C4A	121.1 (2)	C8B—C13B—C12B	122.87 (18)
C6A—C5A—H5A	119.4	C8B—C13B—H13B	118.6
C4A—C5A—H5A	119.4	C12B—C13B—H13B	118.6

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2	0.84	2.05	2.805 (5)	149
O1A—H1A···O2A	0.84	2.21	2.671 (2)	115
O2A—H2A···O1ⁱⁱ	0.84	1.82	2.661 (2)	175
O3A—H3A···O1ⁱⁱ	0.84	1.90	2.739 (2)	180
O1B—H1B···O4ⁱⁱⁱ	0.84	1.95	2.702 (2)	149
O1B—H1B···O2B	0.84	2.29	2.706 (2)	111
O2B—H2B···O3ⁱ	0.84	1.88	2.722 (2)	177
O3B—H3B···O3ⁱ	0.84	1.90	2.735 (2)	174

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

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