Synthesis and crystal structures of two structurally related kryptoracemates

Kryptoracemates are racemic compounds (pairs of enanti­omers) that crystallize in Sohnke space groups (space groups that contain neither inversion centres nor mirror or glide planes nor rotoinversion axes). Thus, the two symmetry-independent mol­ecules cannot be transformed into one another by any symmetry element present in the crystal structure. Usually, the conformation of the two enanti­omers is rather similar if not identical. Sometimes, the two enanti­omers are related by a pseudosymmetry element, which is often a pseudocentre of inversion, because inversion symmetry is thought to be favourable for crystal packing. We obtained crystals of two kryptoracemates of two very similar compounds differing in just one residue, namely rac-N-[(1S,2R,3S)-2-methyl-3-(5-methyl­furan-2-yl)-1-phenyl-3-(pivalamido)­prop­yl]benz­amide, C₂₇H₃₂N₂O₃, (I), and rac-N-[(1S,2S,3R)-2-methyl-3-(5-methyl­furan-2-yl)-1-phenyl-3-(propionamido)­prop­yl]benzamide di­chloro­methane hemisolvate, C₂₅H₂₈N₂O₃·0.5CH₂Cl₂, (II). The crystals of both compounds contain both enanti­omers of these chiral mol­ecules. However, since the space groups [P2₁2₁2₁ for (I) and P1 for (II)] contain neither inversion centres nor mirror or glide planes nor rotoinversion axes, there are both enanti­omers in the asymmetric unit, which is a rather uncommon phenomenon. In addition, it is remarkable that (II) contains two pairs of enanti­omers in the asymmetric unit. In the crystal, mol­ecules are connected by inter­molecular N—H...O hydrogen bonds to form chains or layered structures.

Computing details

For both compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).

(I) rac-N-[(1S,2R,3S)-2-Methyl-3-(5-methylfuran-2-yl)-1-phenyl-3-(pivalamido)propyl]benzamide

Crystal data

C27H32N2O3	Dx = 1.168 Mg m^−3
Mr = 432.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 20981 reflections
a = 9.9801 (4) Å	θ = 2.3–26.3°
b = 18.8540 (8) Å	µ = 0.08 mm^−1
c = 26.1414 (11) Å	T = 173 K
V = 4918.9 (4) Å^3	Needle, colourless
Z = 8	0.26 × 0.09 × 0.09 mm
F(000) = 1856

Data collection

Stoe IPDS II two-circle diffractometer	7086 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.065
ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −12→10
Tmin = 0.405, Tmax = 1.000	k = −19→23
27867 measured reflections	l = −31→32
9562 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0687P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.135	(Δ/σ)max < 0.001
S = 0.98	Δρmax = 0.16 e Å^−3
9562 reflections	Δρmin = −0.19 e Å^−3
595 parameters	Absolute structure: Flack x determined using 2322 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
0 restraints	Absolute structure parameter: 0.6 (10)

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
N1	0.2408 (4)	0.51177 (17)	0.61626 (11)	0.0304 (7)
H1	0.316 (5)	0.525 (2)	0.6150 (12)	0.021 (10)*
N2	0.2002 (4)	0.45934 (19)	0.49954 (12)	0.0367 (8)
H2	0.157 (5)	0.424 (2)	0.4890 (14)	0.032 (11)*
O1	0.0228 (3)	0.53424 (15)	0.63296 (10)	0.0398 (6)
O2	0.2390 (4)	0.57478 (18)	0.48621 (13)	0.0616 (9)
C1	0.1393 (4)	0.55590 (19)	0.62665 (11)	0.0295 (8)
C2	0.2197 (4)	0.43565 (19)	0.61119 (12)	0.0311 (8)
H2B	0.1276	0.4282	0.5972	0.037*
C3	0.3202 (4)	0.4030 (2)	0.57303 (12)	0.0319 (8)
H3	0.4103	0.4043	0.5897	0.038*
C4	0.3302 (4)	0.4474 (2)	0.52308 (12)	0.0332 (8)
H4	0.3662	0.4950	0.5329	0.040*
C5	0.1644 (5)	0.5239 (2)	0.48150 (14)	0.0396 (9)
C6	0.2872 (5)	0.3253 (2)	0.56298 (14)	0.0394 (9)
H6A	0.3521	0.3056	0.5387	0.059*
H6B	0.2916	0.2988	0.5952	0.059*
H6C	0.1968	0.3216	0.5486	0.059*
C11	0.1722 (4)	0.6332 (2)	0.63060 (12)	0.0326 (8)
C12	0.0939 (5)	0.6756 (2)	0.66200 (15)	0.0434 (10)
H12	0.0216	0.6553	0.6805	0.052*
C13	0.1207 (5)	0.7477 (2)	0.66647 (17)	0.0525 (12)
H13	0.0659	0.7768	0.6875	0.063*
C14	0.2274 (6)	0.7767 (2)	0.64021 (16)	0.0493 (11)
H14	0.2477	0.8256	0.6441	0.059*
C15	0.3045 (5)	0.7353 (2)	0.60848 (16)	0.0469 (11)
H15	0.3766	0.7559	0.5899	0.056*
C16	0.2774 (5)	0.6633 (2)	0.60346 (14)	0.0409 (10)
H16	0.3307	0.6348	0.5815	0.049*
C21	0.2272 (4)	0.39814 (19)	0.66312 (13)	0.0323 (8)
C22	0.1350 (4)	0.3460 (2)	0.67604 (14)	0.0382 (9)
H22	0.0655	0.3341	0.6527	0.046*
C23	0.1432 (5)	0.3111 (2)	0.72261 (15)	0.0479 (11)
H23	0.0797	0.2755	0.7311	0.057*
C24	0.2443 (6)	0.3283 (2)	0.75672 (15)	0.0523 (12)
H24	0.2498	0.3047	0.7888	0.063*
C25	0.3365 (5)	0.3793 (2)	0.74427 (15)	0.0485 (11)
H25	0.4066	0.3906	0.7675	0.058*
C26	0.3275 (4)	0.4148 (2)	0.69744 (13)	0.0390 (9)
H26	0.3908	0.4506	0.6892	0.047*
C41	0.4299 (5)	0.4150 (2)	0.48649 (13)	0.0370 (9)
O42	0.3857 (3)	0.39419 (15)	0.43933 (9)	0.0429 (7)
C43	0.4939 (6)	0.3649 (2)	0.41389 (15)	0.0499 (12)
C44	0.6009 (6)	0.3668 (3)	0.44384 (17)	0.0593 (14)
H44	0.6879	0.3497	0.4357	0.071*
C45	0.5605 (6)	0.3994 (3)	0.49090 (16)	0.0555 (13)
H45	0.6158	0.4083	0.5198	0.067*
C46	0.4678 (8)	0.3401 (3)	0.36028 (18)	0.0759 (18)
H46A	0.5495	0.3189	0.3462	0.114*
H46B	0.4410	0.3806	0.3391	0.114*
H46C	0.3959	0.3047	0.3605	0.114*
C51	0.0247 (5)	0.5316 (3)	0.45761 (14)	0.0490 (11)
C52	−0.0584 (8)	0.5750 (5)	0.4958 (2)	0.098 (3)
H52A	−0.0129	0.6200	0.5029	0.147*
H52B	−0.1471	0.5845	0.4812	0.147*
H52C	−0.0685	0.5481	0.5277	0.147*
C53	−0.0428 (6)	0.4613 (4)	0.4456 (2)	0.0798 (19)
H53A	−0.0524	0.4337	0.4772	0.120*
H53B	−0.1314	0.4702	0.4308	0.120*
H53C	0.0120	0.4348	0.4211	0.120*
C54	0.0398 (6)	0.5747 (3)	0.40854 (17)	0.0641 (15)
H54A	0.0834	0.6200	0.4163	0.096*
H54B	0.0947	0.5482	0.3840	0.096*
H54C	−0.0488	0.5836	0.3937	0.096*
N1A	0.7389 (3)	0.52026 (16)	0.63317 (10)	0.0289 (6)
H1A	0.822 (4)	0.5349 (19)	0.6317 (12)	0.018 (8)*
N2A	0.7094 (4)	0.53813 (18)	0.75411 (11)	0.0361 (7)
H2A	0.653 (6)	0.513 (3)	0.7718 (17)	0.056 (15)*
O1A	0.5228 (3)	0.52654 (15)	0.60860 (9)	0.0374 (6)
O2A	0.7562 (4)	0.64987 (16)	0.73078 (12)	0.0612 (10)
C1A	0.6370 (4)	0.55264 (19)	0.60929 (11)	0.0276 (8)
C2A	0.7182 (4)	0.45265 (19)	0.65973 (11)	0.0298 (8)
H2A1	0.6261	0.4531	0.6748	0.036*
C3A	0.8196 (4)	0.4430 (2)	0.70406 (12)	0.0342 (8)
H3A	0.9086	0.4322	0.6883	0.041*
C4A	0.8370 (4)	0.5101 (2)	0.73660 (12)	0.0332 (8)
H4A	0.8774	0.5469	0.7138	0.040*
C5A	0.6779 (5)	0.6078 (2)	0.75005 (14)	0.0404 (10)
C6A	0.7798 (6)	0.3785 (2)	0.73627 (14)	0.0453 (11)
H6A1	0.7698	0.3370	0.7140	0.068*
H6A2	0.8495	0.3691	0.7618	0.068*
H6A3	0.6947	0.3880	0.7536	0.068*
C11A	0.6669 (4)	0.62105 (19)	0.58331 (12)	0.0308 (8)
C12A	0.5963 (5)	0.6379 (2)	0.53877 (13)	0.0389 (9)
H12A	0.5311	0.6060	0.5256	0.047*
C13A	0.6218 (6)	0.7013 (2)	0.51388 (15)	0.0501 (12)
H13A	0.5757	0.7121	0.4831	0.060*
C14A	0.7129 (6)	0.7489 (2)	0.53311 (17)	0.0588 (14)
H14A	0.7282	0.7927	0.5161	0.071*
C15A	0.7822 (6)	0.7326 (2)	0.57743 (17)	0.0577 (13)
H15A	0.8458	0.7653	0.5908	0.069*
C16A	0.7594 (5)	0.6689 (2)	0.60236 (15)	0.0449 (10)
H16A	0.8075	0.6580	0.6327	0.054*
C21A	0.7270 (4)	0.3902 (2)	0.62328 (12)	0.0314 (8)
C22A	0.6332 (5)	0.3357 (2)	0.62459 (13)	0.0380 (9)
H22A	0.5594	0.3386	0.6474	0.046*
C23A	0.6463 (6)	0.2772 (2)	0.59289 (15)	0.0497 (12)
H23A	0.5811	0.2406	0.5939	0.060*
C24A	0.7540 (6)	0.2719 (2)	0.55977 (15)	0.0536 (13)
H24A	0.7640	0.2313	0.5386	0.064*
C25A	0.8470 (5)	0.3262 (3)	0.55784 (14)	0.0485 (11)
H25A	0.9204	0.3231	0.5348	0.058*
C26A	0.8340 (4)	0.3844 (2)	0.58891 (13)	0.0386 (9)
H26A	0.8986	0.4214	0.5871	0.046*
C41A	0.9348 (5)	0.4977 (2)	0.77903 (13)	0.0405 (10)
O42A	0.8837 (3)	0.47704 (15)	0.82568 (9)	0.0445 (7)
C43A	0.9917 (6)	0.4622 (2)	0.85696 (15)	0.0498 (12)
C44A	1.1042 (6)	0.4727 (3)	0.83099 (18)	0.0721 (17)
H44A	1.1926	0.4658	0.8435	0.086*
C45A	1.0680 (5)	0.4964 (3)	0.78063 (17)	0.0631 (15)
H45A	1.1276	0.5088	0.7537	0.076*
C46A	0.9602 (7)	0.4396 (3)	0.90969 (16)	0.0714 (18)
H46D	1.0436	0.4290	0.9280	0.107*
H46E	0.9039	0.3970	0.9087	0.107*
H46F	0.9123	0.4777	0.9274	0.107*
C51A	0.5415 (5)	0.6316 (2)	0.77042 (16)	0.0497 (11)
C52A	0.4746 (8)	0.6725 (5)	0.7269 (3)	0.113 (3)
H52D	0.5338	0.7109	0.7156	0.170*
H52E	0.4573	0.6403	0.6982	0.170*
H52F	0.3897	0.6926	0.7390	0.170*
C53A	0.5716 (8)	0.6805 (4)	0.8151 (2)	0.092 (2)
H53D	0.6302	0.7190	0.8037	0.138*
H53E	0.4877	0.7004	0.8283	0.138*
H53F	0.6164	0.6536	0.8423	0.138*
C54A	0.4522 (6)	0.5729 (3)	0.7880 (3)	0.0763 (17)
H54D	0.4326	0.5412	0.7592	0.114*
H54E	0.4970	0.5460	0.8152	0.114*
H54F	0.3683	0.5928	0.8012	0.114*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0180 (19)	0.0319 (17)	0.0414 (16)	−0.0022 (15)	0.0027 (13)	−0.0005 (12)
N2	0.033 (2)	0.0359 (19)	0.0412 (16)	−0.0010 (16)	−0.0038 (14)	0.0015 (14)
O1	0.0248 (17)	0.0431 (16)	0.0516 (14)	−0.0031 (13)	0.0048 (12)	−0.0051 (12)
O2	0.057 (3)	0.0442 (19)	0.084 (2)	0.0031 (18)	−0.0182 (19)	0.0151 (15)
C1	0.025 (2)	0.035 (2)	0.0283 (15)	0.0002 (16)	0.0018 (14)	−0.0028 (14)
C2	0.023 (2)	0.032 (2)	0.0384 (17)	−0.0016 (16)	0.0010 (15)	−0.0019 (14)
C3	0.028 (2)	0.033 (2)	0.0344 (16)	−0.0006 (17)	0.0011 (14)	0.0007 (14)
C4	0.027 (2)	0.038 (2)	0.0339 (16)	0.0011 (18)	−0.0018 (14)	0.0013 (15)
C5	0.036 (2)	0.044 (2)	0.0388 (18)	0.005 (2)	0.0027 (16)	0.0054 (16)
C6	0.045 (3)	0.034 (2)	0.0391 (18)	−0.0001 (19)	0.0028 (17)	−0.0013 (15)
C11	0.028 (2)	0.036 (2)	0.0333 (16)	0.0033 (17)	−0.0024 (15)	−0.0026 (14)
C12	0.034 (3)	0.045 (3)	0.051 (2)	−0.003 (2)	0.0050 (18)	−0.0144 (18)
C13	0.047 (3)	0.048 (3)	0.063 (2)	0.002 (2)	0.006 (2)	−0.024 (2)
C14	0.056 (3)	0.036 (2)	0.057 (2)	0.003 (2)	−0.006 (2)	−0.0074 (17)
C15	0.053 (3)	0.036 (2)	0.052 (2)	−0.005 (2)	0.008 (2)	0.0065 (17)
C16	0.045 (3)	0.038 (2)	0.0400 (18)	0.001 (2)	0.0082 (18)	0.0027 (15)
C21	0.027 (2)	0.0327 (19)	0.0374 (16)	0.0034 (17)	0.0040 (15)	−0.0019 (14)
C22	0.034 (3)	0.035 (2)	0.0460 (19)	0.0005 (18)	0.0059 (17)	0.0003 (16)
C23	0.055 (3)	0.038 (2)	0.051 (2)	−0.001 (2)	0.017 (2)	0.0079 (17)
C24	0.068 (4)	0.050 (3)	0.040 (2)	0.009 (3)	0.008 (2)	0.0086 (18)
C25	0.049 (3)	0.056 (3)	0.0406 (19)	0.008 (2)	−0.0022 (19)	0.0008 (18)
C26	0.033 (2)	0.046 (2)	0.0383 (18)	−0.0044 (19)	0.0054 (17)	−0.0018 (16)
C41	0.039 (3)	0.038 (2)	0.0346 (17)	0.0014 (18)	0.0014 (17)	0.0056 (15)
O42	0.047 (2)	0.0407 (16)	0.0411 (13)	0.0027 (15)	0.0026 (13)	0.0002 (11)
C43	0.064 (4)	0.040 (2)	0.045 (2)	0.004 (2)	0.016 (2)	−0.0004 (17)
C44	0.056 (4)	0.064 (3)	0.058 (2)	0.021 (3)	0.021 (2)	0.011 (2)
C45	0.043 (3)	0.079 (4)	0.044 (2)	0.009 (3)	0.008 (2)	0.003 (2)
C46	0.109 (6)	0.064 (3)	0.055 (3)	0.001 (4)	0.020 (3)	−0.015 (2)
C51	0.040 (3)	0.066 (3)	0.0413 (19)	0.012 (2)	0.0018 (17)	0.0087 (19)
C52	0.066 (5)	0.162 (7)	0.065 (3)	0.055 (5)	0.010 (3)	0.002 (4)
C53	0.048 (4)	0.103 (5)	0.089 (3)	−0.016 (3)	−0.028 (3)	0.033 (3)
C54	0.052 (4)	0.089 (4)	0.052 (2)	0.011 (3)	−0.009 (2)	0.016 (2)
N1A	0.0177 (18)	0.0316 (16)	0.0373 (14)	−0.0027 (14)	0.0005 (12)	0.0038 (12)
N2A	0.035 (2)	0.0368 (19)	0.0363 (15)	0.0031 (16)	0.0045 (14)	−0.0015 (13)
O1A	0.0214 (16)	0.0404 (15)	0.0505 (13)	−0.0016 (13)	−0.0031 (11)	0.0070 (11)
O2A	0.071 (3)	0.0363 (17)	0.077 (2)	−0.0007 (18)	0.0273 (19)	−0.0047 (14)
C1A	0.024 (2)	0.0296 (18)	0.0293 (15)	−0.0004 (16)	0.0020 (14)	−0.0001 (13)
C2A	0.026 (2)	0.0326 (19)	0.0311 (15)	−0.0015 (17)	0.0001 (14)	0.0049 (13)
C3A	0.032 (2)	0.039 (2)	0.0316 (16)	0.0049 (18)	−0.0023 (15)	0.0000 (14)
C4A	0.033 (2)	0.035 (2)	0.0307 (16)	0.0011 (17)	−0.0010 (15)	−0.0006 (14)
C5A	0.045 (3)	0.037 (2)	0.0391 (18)	0.001 (2)	0.0049 (18)	−0.0054 (16)
C6A	0.064 (3)	0.037 (2)	0.0353 (17)	0.003 (2)	−0.0069 (18)	0.0043 (15)
C11A	0.029 (2)	0.0305 (19)	0.0332 (16)	0.0026 (16)	0.0050 (14)	0.0008 (13)
C12A	0.037 (3)	0.043 (2)	0.0372 (17)	0.005 (2)	0.0037 (16)	0.0025 (16)
C13A	0.060 (3)	0.051 (3)	0.0392 (19)	0.013 (2)	0.003 (2)	0.0129 (18)
C14A	0.079 (4)	0.040 (3)	0.058 (2)	0.002 (3)	0.013 (3)	0.016 (2)
C15A	0.063 (4)	0.044 (3)	0.066 (3)	−0.019 (3)	0.007 (2)	0.003 (2)
C16A	0.047 (3)	0.043 (2)	0.0451 (19)	−0.011 (2)	−0.0034 (19)	0.0054 (17)
C21A	0.028 (2)	0.037 (2)	0.0286 (15)	0.0045 (17)	−0.0022 (14)	0.0012 (13)
C22A	0.038 (3)	0.036 (2)	0.0397 (18)	−0.0022 (19)	−0.0007 (16)	0.0048 (15)
C23A	0.069 (4)	0.033 (2)	0.047 (2)	−0.006 (2)	−0.002 (2)	−0.0019 (17)
C24A	0.072 (4)	0.047 (3)	0.042 (2)	0.010 (3)	−0.001 (2)	−0.0089 (17)
C25A	0.047 (3)	0.062 (3)	0.0372 (18)	0.012 (2)	0.0031 (18)	−0.0059 (18)
C26A	0.031 (2)	0.048 (2)	0.0375 (17)	−0.0001 (19)	−0.0032 (16)	−0.0008 (16)
C41A	0.045 (3)	0.043 (2)	0.0336 (17)	0.003 (2)	−0.0027 (17)	−0.0072 (15)
O42A	0.0480 (19)	0.0501 (17)	0.0355 (12)	−0.0050 (15)	−0.0071 (12)	0.0010 (11)
C43A	0.063 (3)	0.044 (3)	0.0420 (18)	0.006 (2)	−0.019 (2)	−0.0069 (17)
C44A	0.050 (3)	0.107 (5)	0.060 (3)	0.029 (3)	−0.021 (3)	−0.020 (3)
C45A	0.035 (3)	0.108 (5)	0.047 (2)	0.007 (3)	−0.001 (2)	−0.011 (2)
C46A	0.107 (5)	0.059 (3)	0.049 (2)	−0.012 (3)	−0.031 (3)	0.003 (2)
C51A	0.046 (3)	0.046 (3)	0.058 (2)	0.012 (2)	0.005 (2)	−0.0077 (19)
C52A	0.067 (5)	0.153 (8)	0.119 (5)	0.049 (5)	−0.004 (4)	0.047 (5)
C53A	0.094 (6)	0.083 (4)	0.099 (4)	−0.014 (4)	0.050 (4)	−0.041 (3)
C54A	0.043 (4)	0.058 (3)	0.127 (5)	−0.001 (3)	0.031 (3)	−0.014 (3)

Geometric parameters (Å, º)

N1—C1	1.339 (5)	N1A—C1A	1.340 (5)
N1—C2	1.456 (5)	N1A—C2A	1.466 (4)
N1—H1	0.79 (5)	N1A—H1A	0.88 (4)
N2—C5	1.353 (5)	N2A—C5A	1.354 (5)
N2—C4	1.454 (5)	N2A—C4A	1.453 (5)
N2—H2	0.85 (5)	N2A—H2A	0.87 (6)
O1—C1	1.244 (5)	O1A—C1A	1.242 (5)
O2—C5	1.222 (6)	O2A—C5A	1.222 (5)
C1—C11	1.498 (5)	C1A—C11A	1.488 (5)
C2—C21	1.532 (5)	C2A—C21A	1.517 (5)
C2—C3	1.542 (5)	C2A—C3A	1.549 (5)
C2—H2B	1.0000	C2A—H2A1	1.0000
C3—C6	1.524 (5)	C3A—C6A	1.532 (5)
C3—C4	1.554 (5)	C3A—C4A	1.535 (5)
C3—H3	1.0000	C3A—H3A	1.0000
C4—C41	1.509 (5)	C4A—C41A	1.496 (5)
C4—H4	1.0000	C4A—H4A	1.0000
C5—C51	1.534 (6)	C5A—C51A	1.529 (6)
C6—H6A	0.9800	C6A—H6A1	0.9800
C6—H6B	0.9800	C6A—H6A2	0.9800
C6—H6C	0.9800	C6A—H6A3	0.9800
C11—C12	1.387 (5)	C11A—C16A	1.384 (6)
C11—C16	1.389 (6)	C11A—C12A	1.397 (5)
C12—C13	1.390 (6)	C12A—C13A	1.385 (6)
C12—H12	0.9500	C12A—H12A	0.9500
C13—C14	1.380 (7)	C13A—C14A	1.372 (8)
C13—H13	0.9500	C13A—H13A	0.9500
C14—C15	1.375 (6)	C14A—C15A	1.384 (7)
C14—H14	0.9500	C14A—H14A	0.9500
C15—C16	1.390 (6)	C15A—C16A	1.385 (6)
C15—H15	0.9500	C15A—H15A	0.9500
C16—H16	0.9500	C16A—H16A	0.9500
C21—C26	1.381 (6)	C21A—C22A	1.390 (6)
C21—C22	1.388 (6)	C21A—C26A	1.400 (6)
C22—C23	1.386 (6)	C22A—C23A	1.385 (6)
C22—H22	0.9500	C22A—H22A	0.9500
C23—C24	1.385 (7)	C23A—C24A	1.384 (8)
C23—H23	0.9500	C23A—H23A	0.9500
C24—C25	1.370 (7)	C24A—C25A	1.382 (7)
C24—H24	0.9500	C24A—H24A	0.9500
C25—C26	1.398 (5)	C25A—C26A	1.373 (6)
C25—H25	0.9500	C25A—H25A	0.9500
C26—H26	0.9500	C26A—H26A	0.9500
C41—C45	1.341 (7)	C41A—C45A	1.331 (7)
C41—O42	1.367 (5)	C41A—O42A	1.378 (5)
O42—C43	1.383 (6)	O42A—C43A	1.382 (6)
C43—C44	1.325 (8)	C43A—C44A	1.326 (8)
C43—C46	1.500 (6)	C43A—C46A	1.477 (7)
C44—C45	1.434 (6)	C44A—C45A	1.437 (7)
C44—H44	0.9500	C44A—H44A	0.9500
C45—H45	0.9500	C45A—H45A	0.9500
C46—H46A	0.9800	C46A—H46D	0.9800
C46—H46B	0.9800	C46A—H46E	0.9800
C46—H46C	0.9800	C46A—H46F	0.9800
C51—C53	1.520 (8)	C51A—C54A	1.494 (8)
C51—C54	1.526 (6)	C51A—C53A	1.518 (7)
C51—C52	1.534 (7)	C51A—C52A	1.529 (8)
C52—H52A	0.9800	C52A—H52D	0.9800
C52—H52B	0.9800	C52A—H52E	0.9800
C52—H52C	0.9800	C52A—H52F	0.9800
C53—H53A	0.9800	C53A—H53D	0.9800
C53—H53B	0.9800	C53A—H53E	0.9800
C53—H53C	0.9800	C53A—H53F	0.9800
C54—H54A	0.9800	C54A—H54D	0.9800
C54—H54B	0.9800	C54A—H54E	0.9800
C54—H54C	0.9800	C54A—H54F	0.9800
C1—N1—C2	121.5 (4)	C1A—N1A—C2A	120.7 (3)
C1—N1—H1	121 (3)	C1A—N1A—H1A	124 (2)
C2—N1—H1	117 (3)	C2A—N1A—H1A	115 (2)
C5—N2—C4	121.5 (4)	C5A—N2A—C4A	122.1 (4)
C5—N2—H2	118 (3)	C5A—N2A—H2A	115 (4)
C4—N2—H2	118 (3)	C4A—N2A—H2A	122 (4)
O1—C1—N1	122.0 (4)	O1A—C1A—N1A	121.5 (3)
O1—C1—C11	121.0 (3)	O1A—C1A—C11A	121.4 (3)
N1—C1—C11	117.0 (3)	N1A—C1A—C11A	117.1 (3)
N1—C2—C21	111.5 (3)	N1A—C2A—C21A	111.7 (3)
N1—C2—C3	111.0 (3)	N1A—C2A—C3A	111.4 (3)
C21—C2—C3	110.9 (3)	C21A—C2A—C3A	109.9 (3)
N1—C2—H2B	107.7	N1A—C2A—H2A1	107.9
C21—C2—H2B	107.7	C21A—C2A—H2A1	107.9
C3—C2—H2B	107.7	C3A—C2A—H2A1	107.9
C6—C3—C2	110.8 (3)	C6A—C3A—C4A	112.3 (3)
C6—C3—C4	112.7 (3)	C6A—C3A—C2A	109.6 (3)
C2—C3—C4	111.7 (3)	C4A—C3A—C2A	113.0 (3)
C6—C3—H3	107.1	C6A—C3A—H3A	107.2
C2—C3—H3	107.1	C4A—C3A—H3A	107.2
C4—C3—H3	107.1	C2A—C3A—H3A	107.2
N2—C4—C41	112.5 (3)	N2A—C4A—C41A	113.3 (3)
N2—C4—C3	112.4 (3)	N2A—C4A—C3A	112.1 (3)
C41—C4—C3	110.9 (3)	C41A—C4A—C3A	110.9 (3)
N2—C4—H4	106.9	N2A—C4A—H4A	106.7
C41—C4—H4	106.9	C41A—C4A—H4A	106.7
C3—C4—H4	106.9	C3A—C4A—H4A	106.7
O2—C5—N2	120.7 (4)	O2A—C5A—N2A	120.9 (4)
O2—C5—C51	121.3 (4)	O2A—C5A—C51A	121.5 (4)
N2—C5—C51	117.9 (4)	N2A—C5A—C51A	117.6 (4)
C3—C6—H6A	109.5	C3A—C6A—H6A1	109.5
C3—C6—H6B	109.5	C3A—C6A—H6A2	109.5
H6A—C6—H6B	109.5	H6A1—C6A—H6A2	109.5
C3—C6—H6C	109.5	C3A—C6A—H6A3	109.5
H6A—C6—H6C	109.5	H6A1—C6A—H6A3	109.5
H6B—C6—H6C	109.5	H6A2—C6A—H6A3	109.5
C12—C11—C16	119.5 (4)	C16A—C11A—C12A	119.2 (4)
C12—C11—C1	118.6 (4)	C16A—C11A—C1A	122.3 (3)
C16—C11—C1	121.9 (3)	C12A—C11A—C1A	118.5 (4)
C11—C12—C13	120.3 (4)	C13A—C12A—C11A	119.7 (4)
C11—C12—H12	119.8	C13A—C12A—H12A	120.2
C13—C12—H12	119.8	C11A—C12A—H12A	120.2
C14—C13—C12	119.6 (4)	C14A—C13A—C12A	120.9 (4)
C14—C13—H13	120.2	C14A—C13A—H13A	119.5
C12—C13—H13	120.2	C12A—C13A—H13A	119.5
C15—C14—C13	120.5 (4)	C13A—C14A—C15A	119.6 (4)
C15—C14—H14	119.8	C13A—C14A—H14A	120.2
C13—C14—H14	119.8	C15A—C14A—H14A	120.2
C14—C15—C16	120.2 (4)	C14A—C15A—C16A	120.2 (5)
C14—C15—H15	119.9	C14A—C15A—H15A	119.9
C16—C15—H15	119.9	C16A—C15A—H15A	119.9
C11—C16—C15	119.9 (4)	C11A—C16A—C15A	120.4 (4)
C11—C16—H16	120.1	C11A—C16A—H16A	119.8
C15—C16—H16	120.1	C15A—C16A—H16A	119.8
C26—C21—C22	118.9 (3)	C22A—C21A—C26A	118.1 (3)
C26—C21—C2	120.4 (3)	C22A—C21A—C2A	121.3 (3)
C22—C21—C2	120.7 (4)	C26A—C21A—C2A	120.5 (4)
C23—C22—C21	120.7 (4)	C23A—C22A—C21A	120.7 (4)
C23—C22—H22	119.7	C23A—C22A—H22A	119.7
C21—C22—H22	119.7	C21A—C22A—H22A	119.7
C24—C23—C22	119.9 (4)	C24A—C23A—C22A	120.4 (5)
C24—C23—H23	120.1	C24A—C23A—H23A	119.8
C22—C23—H23	120.1	C22A—C23A—H23A	119.8
C25—C24—C23	120.0 (4)	C25A—C24A—C23A	119.4 (4)
C25—C24—H24	120.0	C25A—C24A—H24A	120.3
C23—C24—H24	120.0	C23A—C24A—H24A	120.3
C24—C25—C26	120.0 (4)	C26A—C25A—C24A	120.5 (4)
C24—C25—H25	120.0	C26A—C25A—H25A	119.7
C26—C25—H25	120.0	C24A—C25A—H25A	119.7
C21—C26—C25	120.5 (4)	C25A—C26A—C21A	120.9 (4)
C21—C26—H26	119.8	C25A—C26A—H26A	119.5
C25—C26—H26	119.8	C21A—C26A—H26A	119.5
C45—C41—O42	109.2 (4)	C45A—C41A—O42A	109.7 (4)
C45—C41—C4	132.4 (4)	C45A—C41A—C4A	132.7 (4)
O42—C41—C4	118.4 (4)	O42A—C41A—C4A	117.3 (4)
C41—O42—C43	107.3 (4)	C41A—O42A—C43A	107.0 (4)
C44—C43—O42	109.5 (4)	C44A—C43A—O42A	109.1 (4)
C44—C43—C46	134.4 (5)	C44A—C43A—C46A	134.5 (5)
O42—C43—C46	116.0 (5)	O42A—C43A—C46A	116.4 (5)
C43—C44—C45	107.0 (5)	C43A—C44A—C45A	107.6 (5)
C43—C44—H44	126.5	C43A—C44A—H44A	126.2
C45—C44—H44	126.5	C45A—C44A—H44A	126.2
C41—C45—C44	107.1 (5)	C41A—C45A—C44A	106.6 (5)
C41—C45—H45	126.5	C41A—C45A—H45A	126.7
C44—C45—H45	126.5	C44A—C45A—H45A	126.7
C43—C46—H46A	109.5	C43A—C46A—H46D	109.5
C43—C46—H46B	109.5	C43A—C46A—H46E	109.5
H46A—C46—H46B	109.5	H46D—C46A—H46E	109.5
C43—C46—H46C	109.5	C43A—C46A—H46F	109.5
H46A—C46—H46C	109.5	H46D—C46A—H46F	109.5
H46B—C46—H46C	109.5	H46E—C46A—H46F	109.5
C53—C51—C54	109.5 (4)	C54A—C51A—C53A	109.3 (4)
C53—C51—C52	111.0 (6)	C54A—C51A—C52A	110.0 (6)
C54—C51—C52	108.5 (5)	C53A—C51A—C52A	110.7 (6)
C53—C51—C5	113.8 (4)	C54A—C51A—C5A	114.9 (4)
C54—C51—C5	107.7 (4)	C53A—C51A—C5A	105.7 (5)
C52—C51—C5	106.1 (4)	C52A—C51A—C5A	106.1 (4)
C51—C52—H52A	109.5	C51A—C52A—H52D	109.5
C51—C52—H52B	109.5	C51A—C52A—H52E	109.5
H52A—C52—H52B	109.5	H52D—C52A—H52E	109.5
C51—C52—H52C	109.5	C51A—C52A—H52F	109.5
H52A—C52—H52C	109.5	H52D—C52A—H52F	109.5
H52B—C52—H52C	109.5	H52E—C52A—H52F	109.5
C51—C53—H53A	109.5	C51A—C53A—H53D	109.5
C51—C53—H53B	109.5	C51A—C53A—H53E	109.5
H53A—C53—H53B	109.5	H53D—C53A—H53E	109.5
C51—C53—H53C	109.5	C51A—C53A—H53F	109.5
H53A—C53—H53C	109.5	H53D—C53A—H53F	109.5
H53B—C53—H53C	109.5	H53E—C53A—H53F	109.5
C51—C54—H54A	109.5	C51A—C54A—H54D	109.5
C51—C54—H54B	109.5	C51A—C54A—H54E	109.5
H54A—C54—H54B	109.5	H54D—C54A—H54E	109.5
C51—C54—H54C	109.5	C51A—C54A—H54F	109.5
H54A—C54—H54C	109.5	H54D—C54A—H54F	109.5
H54B—C54—H54C	109.5	H54E—C54A—H54F	109.5
C2—N1—C1—O1	0.7 (5)	C2A—N1A—C1A—O1A	−0.4 (5)
C2—N1—C1—C11	−179.5 (3)	C2A—N1A—C1A—C11A	−180.0 (3)
C1—N1—C2—C21	−86.6 (4)	C1A—N1A—C2A—C21A	84.0 (4)
C1—N1—C2—C3	149.2 (3)	C1A—N1A—C2A—C3A	−152.7 (3)
N1—C2—C3—C6	−173.2 (3)	N1A—C2A—C3A—C6A	170.4 (3)
C21—C2—C3—C6	62.2 (4)	C21A—C2A—C3A—C6A	−65.3 (4)
N1—C2—C3—C4	−46.6 (4)	N1A—C2A—C3A—C4A	44.3 (4)
C21—C2—C3—C4	−171.2 (3)	C21A—C2A—C3A—C4A	168.6 (3)
C5—N2—C4—C41	−98.6 (4)	C5A—N2A—C4A—C41A	101.2 (4)
C5—N2—C4—C3	135.3 (4)	C5A—N2A—C4A—C3A	−132.5 (3)
C6—C3—C4—N2	72.0 (4)	C6A—C3A—C4A—N2A	−72.8 (4)
C2—C3—C4—N2	−53.6 (4)	C2A—C3A—C4A—N2A	51.9 (4)
C6—C3—C4—C41	−55.0 (5)	C6A—C3A—C4A—C41A	54.8 (5)
C2—C3—C4—C41	179.4 (3)	C2A—C3A—C4A—C41A	179.5 (3)
C4—N2—C5—O2	−2.7 (6)	C4A—N2A—C5A—O2A	0.8 (6)
C4—N2—C5—C51	−179.6 (3)	C4A—N2A—C5A—C51A	−179.2 (3)
O1—C1—C11—C12	28.3 (5)	O1A—C1A—C11A—C16A	145.9 (4)
N1—C1—C11—C12	−151.5 (3)	N1A—C1A—C11A—C16A	−34.5 (5)
O1—C1—C11—C16	−151.1 (4)	O1A—C1A—C11A—C12A	−32.5 (5)
N1—C1—C11—C16	29.1 (5)	N1A—C1A—C11A—C12A	147.1 (3)
C16—C11—C12—C13	−0.2 (6)	C16A—C11A—C12A—C13A	1.3 (6)
C1—C11—C12—C13	−179.6 (4)	C1A—C11A—C12A—C13A	179.8 (4)
C11—C12—C13—C14	−1.2 (7)	C11A—C12A—C13A—C14A	−1.8 (7)
C12—C13—C14—C15	2.1 (7)	C12A—C13A—C14A—C15A	1.4 (8)
C13—C14—C15—C16	−1.4 (7)	C13A—C14A—C15A—C16A	−0.3 (8)
C12—C11—C16—C15	0.9 (6)	C12A—C11A—C16A—C15A	−0.3 (7)
C1—C11—C16—C15	−179.7 (4)	C1A—C11A—C16A—C15A	−178.8 (4)
C14—C15—C16—C11	−0.1 (7)	C14A—C15A—C16A—C11A	−0.1 (8)
N1—C2—C21—C26	−44.4 (5)	N1A—C2A—C21A—C22A	−134.5 (4)
C3—C2—C21—C26	79.9 (4)	C3A—C2A—C21A—C22A	101.3 (4)
N1—C2—C21—C22	136.9 (4)	N1A—C2A—C21A—C26A	48.5 (5)
C3—C2—C21—C22	−98.8 (4)	C3A—C2A—C21A—C26A	−75.7 (4)
C26—C21—C22—C23	0.0 (6)	C26A—C21A—C22A—C23A	0.4 (6)
C2—C21—C22—C23	178.7 (4)	C2A—C21A—C22A—C23A	−176.6 (4)
C21—C22—C23—C24	0.0 (6)	C21A—C22A—C23A—C24A	0.7 (6)
C22—C23—C24—C25	−0.5 (7)	C22A—C23A—C24A—C25A	−1.3 (7)
C23—C24—C25—C26	0.9 (7)	C23A—C24A—C25A—C26A	0.9 (7)
C22—C21—C26—C25	0.5 (6)	C24A—C25A—C26A—C21A	0.2 (6)
C2—C21—C26—C25	−178.3 (4)	C22A—C21A—C26A—C25A	−0.8 (6)
C24—C25—C26—C21	−0.9 (7)	C2A—C21A—C26A—C25A	176.2 (4)
N2—C4—C41—C45	175.4 (5)	N2A—C4A—C41A—C45A	−153.6 (5)
C3—C4—C41—C45	−57.7 (6)	C3A—C4A—C41A—C45A	79.5 (6)
N2—C4—C41—O42	−6.8 (5)	N2A—C4A—C41A—O42A	33.4 (5)
C3—C4—C41—O42	120.2 (4)	C3A—C4A—C41A—O42A	−93.6 (4)
C45—C41—O42—C43	−0.1 (5)	C45A—C41A—O42A—C43A	−0.3 (5)
C4—C41—O42—C43	−178.5 (3)	C4A—C41A—O42A—C43A	174.3 (3)
C41—O42—C43—C44	0.4 (5)	C41A—O42A—C43A—C44A	−0.3 (5)
C41—O42—C43—C46	−178.4 (4)	C41A—O42A—C43A—C46A	179.3 (4)
O42—C43—C44—C45	−0.5 (6)	O42A—C43A—C44A—C45A	0.8 (6)
C46—C43—C44—C45	178.1 (5)	C46A—C43A—C44A—C45A	−178.7 (5)
O42—C41—C45—C44	−0.2 (5)	O42A—C41A—C45A—C44A	0.8 (6)
C4—C41—C45—C44	177.9 (4)	C4A—C41A—C45A—C44A	−172.7 (5)
C43—C44—C45—C41	0.4 (6)	C43A—C44A—C45A—C41A	−1.0 (7)
O2—C5—C51—C53	168.9 (5)	O2A—C5A—C51A—C54A	174.2 (5)
N2—C5—C51—C53	−14.2 (5)	N2A—C5A—C51A—C54A	−5.9 (6)
O2—C5—C51—C54	47.3 (6)	O2A—C5A—C51A—C53A	−65.2 (6)
N2—C5—C51—C54	−135.8 (4)	N2A—C5A—C51A—C53A	114.7 (5)
O2—C5—C51—C52	−68.7 (6)	O2A—C5A—C51A—C52A	52.4 (7)
N2—C5—C51—C52	108.2 (5)	N2A—C5A—C51A—C52A	−127.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1A	0.79 (5)	2.07 (5)	2.835 (4)	161 (4)
C3—H3···O1A	1.00	2.61	3.222 (5)	120
C4—H4···O1A	1.00	2.59	3.304 (5)	128
N1A—H1A···O1^i	0.88 (4)	2.00 (4)	2.846 (4)	161 (3)
C4A—H4A···O1^i	1.00	2.57	3.314 (4)	131
C46A—H46D···O2^ii	0.98	2.65	3.617 (7)	169

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

(II) rac-N-[(1S,2S,3R)-2-Methyl-3-(5-methylfuran-2-yl)-1-phenyl-3-(propionamido)propyl]benzamide dichloromethane hemisolvate

Crystal data

C25H28N2O3·0.5CH2Cl2	Z = 4
Mr = 446.96	F(000) = 948
Triclinic, P1	Dx = 1.195 Mg m^−3
a = 10.1501 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.8556 (15) Å	Cell parameters from 16955 reflections
c = 17.662 (2) Å	θ = 3.4–25.9°
α = 109.248 (8)°	µ = 0.18 mm^−1
β = 97.929 (9)°	T = 173 K
γ = 91.214 (8)°	Needle, colourless
V = 2483.9 (5) Å^3	0.22 × 0.13 × 0.13 mm

Data collection

Stoe IPDS II two-circle diffractometer	9998 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.079
ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −12→12
Tmin = 0.620, Tmax = 1.000	k = −17→17
19477 measured reflections	l = −19→21
14382 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.0968P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.195	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.34 e Å^−3
14382 reflections	Δρmin = −0.46 e Å^−3
1163 parameters	Absolute structure: Flack x determined using 2795 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
11 restraints	Absolute structure parameter: 0.1 (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
N1	0.7623 (6)	0.1857 (5)	0.2102 (4)	0.0364 (16)
H1	0.852 (2)	0.192 (7)	0.228 (5)	0.044*
N2	0.5456 (5)	0.3866 (5)	0.1174 (4)	0.0285 (14)
H2	0.527 (7)	0.414 (5)	0.1682 (19)	0.034*
O1	0.5598 (5)	0.1637 (5)	0.2433 (4)	0.0495 (16)
O2	0.4639 (5)	0.3555 (5)	−0.0153 (3)	0.0410 (14)
C1	0.6836 (7)	0.1627 (6)	0.2562 (5)	0.0344 (18)
C2	0.7118 (7)	0.2217 (6)	0.1447 (5)	0.0374 (19)
H2D	0.6123	0.2181	0.1395	0.045*
C3	0.7592 (7)	0.3272 (6)	0.1655 (4)	0.0326 (18)
H3	0.8564	0.3301	0.1613	0.039*
C4	0.6836 (6)	0.3698 (5)	0.1023 (4)	0.0267 (16)
H4	0.6797	0.3212	0.0470	0.032*
C5	0.4479 (7)	0.3841 (6)	0.0565 (4)	0.0278 (16)
C6	0.7428 (7)	0.3867 (6)	0.2524 (4)	0.0313 (17)
H6A	0.7739	0.4534	0.2635	0.047*
H6B	0.6485	0.3834	0.2586	0.047*
H6C	0.7954	0.3614	0.2907	0.047*
C11	0.7482 (7)	0.1363 (6)	0.3268 (5)	0.0339 (17)
C12	0.8853 (8)	0.1415 (7)	0.3516 (6)	0.046 (2)
H12	0.9442	0.1629	0.3227	0.056*
C13	0.9366 (10)	0.1161 (8)	0.4176 (6)	0.057 (3)
H13	1.0305	0.1200	0.4332	0.069*
C14	0.8552 (11)	0.0852 (8)	0.4612 (7)	0.062 (3)
H14	0.8916	0.0688	0.5071	0.074*
C15	0.7215 (12)	0.0786 (10)	0.4373 (8)	0.077 (4)
H15	0.6637	0.0557	0.4659	0.092*
C16	0.6676 (10)	0.1047 (8)	0.3715 (7)	0.061 (3)
H16	0.5735	0.1009	0.3568	0.073*
C21	0.7476 (9)	0.1592 (6)	0.0636 (6)	0.045 (2)
C22	0.8829 (10)	0.1529 (9)	0.0513 (6)	0.064 (3)
H22	0.9503	0.1881	0.0947	0.077*
C23	0.9214 (13)	0.0968 (9)	−0.0222 (6)	0.074 (4)
H23	1.0128	0.0947	−0.0287	0.088*
C24	0.8256 (18)	0.0459 (9)	−0.0837 (8)	0.082 (4)
H24	0.8498	0.0082	−0.1340	0.099*
C25	0.6974 (17)	0.0482 (9)	−0.0742 (7)	0.080 (4)
H25	0.6322	0.0099	−0.1174	0.096*
C26	0.6550 (14)	0.1082 (8)	0.0008 (7)	0.072 (3)
H26	0.5629	0.1112	0.0053	0.087*
C41	0.7539 (6)	0.4590 (6)	0.1027 (4)	0.0281 (16)
O42	0.8498 (5)	0.4489 (4)	0.0540 (3)	0.0338 (12)
C43	0.8992 (7)	0.5399 (6)	0.0632 (5)	0.0333 (18)
C44	0.8382 (8)	0.6044 (6)	0.1160 (5)	0.0388 (19)
H44	0.8544	0.6719	0.1332	0.047*
C45	0.7434 (7)	0.5529 (6)	0.1420 (5)	0.0359 (18)
H45	0.6845	0.5796	0.1796	0.043*
C46	1.0015 (9)	0.5445 (8)	0.0100 (6)	0.053 (2)
H46A	1.0764	0.5073	0.0201	0.080*
H46B	1.0339	0.6112	0.0225	0.080*
H46C	0.9608	0.5180	−0.0471	0.080*
C51	0.3144 (7)	0.4155 (7)	0.0814 (5)	0.039 (2)
H51A	0.3241	0.4410	0.1414	0.047*
H51B	0.2871	0.4678	0.0607	0.047*
C52	0.2066 (9)	0.3345 (9)	0.0495 (7)	0.062 (3)
H52A	0.1225	0.3580	0.0670	0.094*
H52B	0.1953	0.3099	−0.0100	0.094*
H52C	0.2323	0.2832	0.0707	0.094*
N1A	0.8171 (5)	0.7983 (5)	0.8745 (4)	0.0296 (14)
H1A	0.9068 (16)	0.801 (6)	0.887 (5)	0.035*
N2A	0.5707 (5)	0.5918 (5)	0.6714 (4)	0.0273 (13)
H2A	0.544 (7)	0.565 (5)	0.707 (4)	0.033*
O1A	0.6138 (5)	0.8146 (4)	0.9142 (4)	0.0399 (14)
O2A	0.4900 (5)	0.6365 (5)	0.5630 (3)	0.0401 (14)
C1A	0.7371 (6)	0.8179 (6)	0.9317 (4)	0.0285 (16)
C2A	0.7623 (7)	0.7590 (6)	0.7872 (5)	0.0332 (17)
H2E	0.6630	0.7599	0.7824	0.040*
C3A	0.7951 (7)	0.6542 (5)	0.7505 (4)	0.0276 (16)
H3A	0.8915	0.6540	0.7443	0.033*
C4A	0.7122 (6)	0.6088 (6)	0.6643 (4)	0.0290 (17)
H4A	0.7163	0.6558	0.6351	0.035*
C5A	0.4717 (7)	0.6022 (6)	0.6163 (4)	0.0281 (16)
C6A	0.7733 (7)	0.5953 (6)	0.8050 (4)	0.0321 (17)
H6A1	0.7954	0.5294	0.7791	0.048*
H6A2	0.8308	0.6233	0.8576	0.048*
H6A3	0.6798	0.5955	0.8133	0.048*
C11A	0.8021 (7)	0.8440 (5)	1.0175 (4)	0.0284 (16)
C12A	0.9273 (8)	0.8191 (7)	1.0421 (5)	0.0403 (19)
H12A	0.9796	0.7868	1.0020	0.048*
C13A	0.9789 (9)	0.8400 (8)	1.1234 (6)	0.051 (2)
H13A	1.0649	0.8214	1.1384	0.061*
C14A	0.9054 (10)	0.8874 (8)	1.1821 (6)	0.058 (3)
H14A	0.9411	0.9030	1.2379	0.070*
C15A	0.7787 (11)	0.9124 (8)	1.1597 (6)	0.057 (3)
H15A	0.7265	0.9436	1.2002	0.068*
C16A	0.7283 (8)	0.8919 (7)	1.0787 (6)	0.046 (2)
H16A	0.6422	0.9105	1.0640	0.056*
C21A	0.8096 (8)	0.8227 (6)	0.7425 (5)	0.0359 (18)
C22A	0.9458 (9)	0.8423 (7)	0.7445 (6)	0.047 (2)
H22A	1.0091	0.8137	0.7725	0.056*
C23A	0.9903 (11)	0.9025 (8)	0.7063 (7)	0.062 (3)
H23A	1.0831	0.9147	0.7080	0.074*
C24A	0.8981 (14)	0.9444 (7)	0.6659 (6)	0.066 (3)
H24A	0.9278	0.9853	0.6392	0.079*
C25A	0.7612 (14)	0.9273 (8)	0.6640 (7)	0.070 (3)
H25A	0.6982	0.9570	0.6367	0.083*
C26A	0.7187 (11)	0.8667 (7)	0.7023 (6)	0.052 (2)
H26A	0.6259	0.8551	0.7010	0.062*
C41A	0.7648 (6)	0.5189 (6)	0.6155 (4)	0.0287 (17)
O42A	0.8596 (4)	0.5281 (4)	0.5700 (3)	0.0317 (12)
C43A	0.8936 (7)	0.4358 (6)	0.5294 (5)	0.0344 (18)
C44A	0.8241 (7)	0.3718 (6)	0.5499 (5)	0.0337 (17)
H44A	0.8302	0.3045	0.5317	0.040*
C45A	0.7391 (7)	0.4243 (6)	0.6043 (5)	0.0346 (18)
H45A	0.6764	0.3984	0.6283	0.042*
C46A	0.9953 (8)	0.4287 (8)	0.4738 (6)	0.050 (2)
H46D	1.0092	0.3613	0.4467	0.074*
H46E	1.0796	0.4622	0.5055	0.074*
H46F	0.9633	0.4579	0.4330	0.074*
C51A	0.3323 (7)	0.5730 (7)	0.6266 (5)	0.038 (2)
H51C	0.2909	0.5221	0.5762	0.046*
H51D	0.3394	0.5462	0.6713	0.046*
C52A	0.2432 (10)	0.6548 (9)	0.6447 (7)	0.067 (3)
H52D	0.1552	0.6319	0.6506	0.100*
H52E	0.2824	0.7049	0.6952	0.100*
H52F	0.2339	0.6807	0.6001	0.100*
N1B	0.4947 (5)	0.5337 (5)	0.3856 (4)	0.0299 (14)
H1B	0.498 (8)	0.552 (6)	0.4403 (11)	0.036*
N2B	0.3005 (5)	0.2470 (5)	0.2912 (4)	0.0306 (14)
H2B	0.366 (6)	0.207 (5)	0.275 (5)	0.037*
O1B	0.5052 (5)	0.5463 (4)	0.2625 (3)	0.0335 (12)
O2B	0.0793 (5)	0.2236 (5)	0.2436 (3)	0.0418 (14)
C1B	0.5423 (6)	0.5743 (5)	0.3361 (4)	0.0256 (15)
C2B	0.3863 (6)	0.4570 (6)	0.3524 (4)	0.0300 (17)
H2G	0.4010	0.4165	0.2970	0.036*
C3B	0.3925 (6)	0.3934 (6)	0.4071 (4)	0.0279 (16)
H3B	0.3735	0.4335	0.4616	0.033*
C4B	0.2850 (7)	0.3101 (6)	0.3719 (5)	0.0323 (17)
H4B	0.1963	0.3377	0.3678	0.039*
C5B	0.1947 (7)	0.2045 (6)	0.2342 (5)	0.0320 (17)
C6B	0.5332 (7)	0.3573 (6)	0.4185 (5)	0.0349 (18)
H6B1	0.5994	0.4121	0.4409	0.052*
H6B2	0.5362	0.3209	0.4558	0.052*
H6B3	0.5533	0.3162	0.3659	0.052*
C11B	0.6448 (7)	0.6568 (6)	0.3759 (5)	0.0299 (16)
C12B	0.6585 (8)	0.7244 (7)	0.3370 (6)	0.046 (2)
H12B	0.6021	0.7182	0.2877	0.055*
C13B	0.7530 (10)	0.7991 (8)	0.3703 (7)	0.059 (3)
H13B	0.7624	0.8441	0.3434	0.071*
C14B	0.8345 (10)	0.8103 (8)	0.4419 (7)	0.060 (3)
H14B	0.8989	0.8631	0.4645	0.072*
C15B	0.8229 (8)	0.7441 (8)	0.4819 (6)	0.053 (2)
H15B	0.8792	0.7517	0.5315	0.064*
C16B	0.7284 (7)	0.6673 (6)	0.4484 (5)	0.0376 (18)
H16B	0.7206	0.6217	0.4750	0.045*
C21B	0.2524 (6)	0.5019 (6)	0.3446 (5)	0.0295 (17)
C22B	0.2205 (7)	0.5807 (6)	0.4061 (5)	0.0327 (17)
H22B	0.2813	0.6055	0.4553	0.039*
C23B	0.1034 (8)	0.6239 (7)	0.3979 (5)	0.042 (2)
H23B	0.0831	0.6777	0.4406	0.051*
C24B	0.0141 (7)	0.5864 (7)	0.3243 (5)	0.042 (2)
H24B	−0.0673	0.6152	0.3173	0.050*
C25B	0.0434 (8)	0.5101 (7)	0.2640 (6)	0.043 (2)
H25B	−0.0173	0.4863	0.2148	0.052*
C26B	0.1616 (6)	0.4649 (6)	0.2724 (5)	0.0340 (18)
H26B	0.1800	0.4102	0.2299	0.041*
C41B	0.2841 (7)	0.2514 (6)	0.4284 (5)	0.0335 (18)
O42B	0.2578 (5)	0.2985 (4)	0.5042 (3)	0.0386 (13)
C43B	0.2665 (8)	0.2360 (7)	0.5471 (5)	0.0384 (19)
C44B	0.3016 (8)	0.1515 (8)	0.4982 (6)	0.052 (3)
H44B	0.3169	0.0959	0.5126	0.062*
C45B	0.3116 (8)	0.1611 (7)	0.4213 (6)	0.046 (2)
H45B	0.3332	0.1134	0.3746	0.055*
C46B	0.2354 (11)	0.2712 (9)	0.6301 (6)	0.063 (3)
H46G	0.2460	0.2207	0.6543	0.094*
H46H	0.1433	0.2898	0.6290	0.094*
H46I	0.2963	0.3268	0.6626	0.094*
C51B	0.2250 (8)	0.1329 (7)	0.1583 (5)	0.042 (2)
H51E	0.3227	0.1293	0.1611	0.051*
H51F	0.1914	0.1529	0.1114	0.051*
C52B	0.1592 (13)	0.0343 (8)	0.1466 (8)	0.074 (3)
H52G	0.1798	−0.0122	0.0965	0.111*
H52H	0.1934	0.0143	0.1928	0.111*
H52I	0.0623	0.0379	0.1432	0.111*
N1C	0.4892 (6)	0.4580 (5)	0.8639 (4)	0.0316 (15)
H1C	0.498 (8)	0.430 (6)	0.903 (4)	0.038*
N2C	0.3462 (5)	0.7437 (5)	0.9315 (4)	0.0312 (15)
H2C	0.432 (3)	0.748 (6)	0.923 (5)	0.037*
O1C	0.5024 (5)	0.4422 (4)	0.7339 (3)	0.0346 (12)
O2C	0.1296 (5)	0.7701 (5)	0.8974 (4)	0.0423 (15)
C1C	0.5327 (6)	0.4155 (6)	0.7936 (4)	0.0282 (16)
C2C	0.3950 (6)	0.5335 (6)	0.8733 (5)	0.0294 (17)
H2F	0.4191	0.5740	0.8412	0.035*
C3C	0.4115 (7)	0.5967 (6)	0.9621 (4)	0.0295 (16)
H3C	0.3857	0.5559	0.9936	0.035*
C4C	0.3159 (7)	0.6797 (6)	0.9753 (5)	0.0305 (17)
H4C	0.2225	0.6511	0.9541	0.037*
C5C	0.2495 (7)	0.7890 (6)	0.9004 (5)	0.0349 (18)
C6C	0.5552 (7)	0.6336 (6)	0.9947 (5)	0.040 (2)
H6C1	0.5626	0.6739	1.0518	0.059*
H6C2	0.6109	0.5795	0.9902	0.059*
H6C3	0.5853	0.6713	0.9633	0.059*
C11C	0.6208 (7)	0.3348 (6)	0.7896 (5)	0.0311 (17)
C12C	0.6248 (8)	0.2669 (7)	0.7148 (5)	0.042 (2)
H12C	0.5718	0.2717	0.6677	0.051*
C13C	0.7082 (10)	0.1896 (7)	0.7082 (6)	0.054 (2)
H13C	0.7135	0.1434	0.6568	0.065*
C14C	0.7822 (10)	0.1832 (8)	0.7791 (7)	0.060 (3)
H14C	0.8356	0.1307	0.7760	0.072*
C15C	0.7782 (8)	0.2525 (7)	0.8531 (6)	0.048 (2)
H15C	0.8306	0.2485	0.9007	0.058*
C16C	0.6978 (7)	0.3277 (6)	0.8581 (5)	0.0378 (19)
H16C	0.6955	0.3752	0.9094	0.045*
C21C	0.2532 (6)	0.4877 (6)	0.8372 (4)	0.0300 (17)
C22C	0.2078 (7)	0.4089 (6)	0.8544 (5)	0.0358 (19)
H22C	0.2631	0.3848	0.8903	0.043*
C23C	0.0790 (8)	0.3644 (7)	0.8185 (5)	0.042 (2)
H23C	0.0473	0.3107	0.8304	0.051*
C24C	0.0009 (7)	0.3991 (7)	0.7668 (5)	0.042 (2)
H24C	−0.0856	0.3694	0.7428	0.050*
C25C	0.0458 (7)	0.4764 (7)	0.7490 (5)	0.043 (2)
H25C	−0.0088	0.4987	0.7117	0.051*
C26C	0.1712 (7)	0.5226 (7)	0.7852 (5)	0.0370 (19)
H26C	0.2002	0.5777	0.7744	0.044*
C41C	0.3240 (7)	0.7363 (6)	1.0638 (5)	0.0314 (18)
O42C	0.2826 (5)	0.6873 (4)	1.1118 (3)	0.0381 (13)
C43C	0.3053 (8)	0.7480 (7)	1.1912 (5)	0.040 (2)
C44C	0.3618 (9)	0.8323 (8)	1.1937 (6)	0.055 (3)
H44C	0.3898	0.8863	1.2408	0.066*
C45C	0.3717 (8)	0.8246 (7)	1.1109 (5)	0.043 (2)
H45C	0.4057	0.8731	1.0933	0.051*
C46C	0.2632 (12)	0.7105 (9)	1.2524 (7)	0.067 (3)
H46J	0.2855	0.7591	1.3064	0.100*
H46K	0.3095	0.6530	1.2514	0.100*
H46L	0.1667	0.6946	1.2402	0.100*
C51C	0.2989 (8)	0.8650 (7)	0.8690 (5)	0.042 (2)
H51G	0.3935	0.8569	0.8619	0.050*
H51H	0.2465	0.8574	0.8154	0.050*
C52C	0.2866 (18)	0.9611 (11)	0.9255 (11)	0.109 (5)
H52J	0.3190	1.0089	0.9040	0.163*
H52K	0.1928	0.9695	0.9319	0.163*
H52L	0.3396	0.9690	0.9783	0.163*
C1L	0.407 (2)	0.8249 (14)	0.5041 (12)	0.122 (6)
H1L1	0.4784	0.8039	0.5370	0.146*
H1L2	0.3706	0.7686	0.4563	0.146*
Cl12	0.4699 (6)	0.9053 (4)	0.4728 (5)	0.155 (2)
Cl11	0.2856 (14)	0.8630 (8)	0.5592 (8)	0.300 (7)
C2L	0.365 (2)	0.1596 (16)	0.8149 (12)	0.134 (7)
H2L1	0.3738	0.2146	0.7957	0.161*
H2L2	0.4225	0.1748	0.8682	0.161*
Cl21	0.2019 (8)	0.1412 (6)	0.8256 (6)	0.210 (4)
Cl22	0.4150 (9)	0.0620 (8)	0.7485 (6)	0.216 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.027 (3)	0.040 (4)	0.047 (4)	−0.001 (3)	0.000 (3)	0.024 (4)
N2	0.024 (3)	0.038 (4)	0.027 (3)	0.004 (3)	0.005 (2)	0.017 (3)
O1	0.026 (3)	0.067 (5)	0.056 (4)	0.007 (3)	0.008 (2)	0.020 (4)
O2	0.039 (3)	0.056 (4)	0.029 (3)	0.009 (3)	0.002 (2)	0.018 (3)
C1	0.033 (4)	0.021 (4)	0.045 (5)	0.002 (3)	0.005 (3)	0.006 (4)
C2	0.032 (4)	0.032 (5)	0.041 (5)	−0.003 (3)	−0.008 (3)	0.009 (4)
C3	0.027 (3)	0.043 (5)	0.027 (4)	0.007 (3)	−0.002 (3)	0.014 (4)
C4	0.023 (3)	0.030 (4)	0.026 (4)	0.002 (3)	−0.001 (3)	0.010 (3)
C5	0.032 (4)	0.029 (5)	0.026 (4)	−0.002 (3)	0.002 (3)	0.014 (3)
C6	0.033 (4)	0.033 (5)	0.026 (4)	0.008 (3)	−0.001 (3)	0.009 (3)
C11	0.043 (4)	0.023 (4)	0.037 (4)	0.005 (3)	0.019 (3)	0.006 (4)
C12	0.046 (5)	0.054 (6)	0.044 (5)	−0.001 (4)	0.006 (4)	0.024 (5)
C13	0.062 (6)	0.070 (8)	0.047 (6)	−0.002 (5)	0.004 (4)	0.032 (6)
C14	0.083 (7)	0.054 (7)	0.064 (7)	0.011 (5)	0.025 (5)	0.034 (6)
C15	0.077 (8)	0.091 (10)	0.093 (9)	0.003 (7)	0.035 (6)	0.063 (9)
C16	0.052 (5)	0.071 (8)	0.073 (7)	0.003 (5)	0.021 (5)	0.039 (6)
C21	0.065 (6)	0.026 (5)	0.046 (5)	0.005 (4)	0.000 (4)	0.018 (4)
C22	0.065 (6)	0.066 (8)	0.047 (6)	0.033 (5)	−0.006 (5)	0.005 (5)
C23	0.101 (8)	0.075 (9)	0.036 (6)	0.053 (7)	0.014 (5)	0.003 (6)
C24	0.153 (13)	0.041 (7)	0.051 (7)	0.024 (8)	0.020 (8)	0.012 (6)
C25	0.136 (12)	0.037 (7)	0.046 (7)	−0.028 (7)	−0.013 (7)	−0.002 (5)
C26	0.116 (9)	0.042 (7)	0.052 (6)	−0.030 (6)	−0.016 (6)	0.019 (5)
C41	0.025 (3)	0.040 (5)	0.021 (4)	0.009 (3)	0.004 (3)	0.011 (3)
O42	0.026 (2)	0.041 (4)	0.033 (3)	0.005 (2)	0.005 (2)	0.011 (3)
C43	0.022 (3)	0.044 (5)	0.039 (4)	0.002 (3)	0.001 (3)	0.023 (4)
C44	0.039 (4)	0.031 (5)	0.045 (5)	0.003 (4)	0.000 (4)	0.014 (4)
C45	0.039 (4)	0.037 (5)	0.034 (4)	0.008 (4)	0.006 (3)	0.015 (4)
C46	0.043 (5)	0.062 (7)	0.064 (7)	0.004 (4)	0.016 (4)	0.031 (6)
C51	0.026 (4)	0.055 (6)	0.044 (5)	−0.003 (3)	0.001 (3)	0.029 (5)
C52	0.038 (5)	0.079 (9)	0.068 (7)	−0.016 (5)	0.001 (4)	0.025 (6)
N1A	0.026 (3)	0.031 (4)	0.028 (3)	0.002 (3)	0.001 (2)	0.006 (3)
N2A	0.027 (3)	0.028 (4)	0.028 (3)	0.002 (2)	0.004 (2)	0.009 (3)
O1A	0.023 (3)	0.050 (4)	0.049 (3)	0.006 (2)	0.009 (2)	0.019 (3)
O2A	0.038 (3)	0.060 (4)	0.027 (3)	0.005 (3)	0.001 (2)	0.022 (3)
C1A	0.026 (4)	0.027 (5)	0.033 (4)	0.002 (3)	0.008 (3)	0.009 (3)
C2A	0.030 (4)	0.032 (5)	0.037 (4)	0.002 (3)	0.002 (3)	0.013 (4)
C3A	0.029 (3)	0.030 (5)	0.024 (4)	0.005 (3)	0.001 (3)	0.012 (3)
C4A	0.021 (3)	0.039 (5)	0.035 (4)	0.001 (3)	0.003 (3)	0.024 (4)
C5A	0.033 (4)	0.029 (4)	0.017 (3)	0.006 (3)	0.006 (3)	0.000 (3)
C6A	0.035 (4)	0.035 (5)	0.026 (4)	0.002 (3)	−0.004 (3)	0.015 (4)
C11A	0.035 (4)	0.018 (4)	0.029 (4)	−0.003 (3)	0.010 (3)	0.001 (3)
C12A	0.046 (4)	0.040 (5)	0.035 (4)	−0.004 (4)	0.004 (3)	0.013 (4)
C13A	0.051 (5)	0.054 (7)	0.045 (5)	−0.010 (4)	−0.007 (4)	0.019 (5)
C14A	0.075 (7)	0.064 (7)	0.029 (5)	−0.013 (5)	0.004 (4)	0.008 (5)
C15A	0.080 (7)	0.055 (7)	0.033 (5)	−0.002 (5)	0.021 (4)	0.006 (5)
C16A	0.040 (4)	0.051 (6)	0.047 (5)	−0.001 (4)	0.013 (4)	0.012 (5)
C21A	0.047 (4)	0.025 (5)	0.031 (4)	0.007 (3)	0.000 (3)	0.004 (3)
C22A	0.053 (5)	0.049 (6)	0.041 (5)	0.004 (4)	0.011 (4)	0.016 (5)
C23A	0.073 (7)	0.052 (7)	0.063 (7)	−0.012 (5)	0.012 (5)	0.023 (6)
C24A	0.122 (10)	0.029 (6)	0.041 (6)	−0.013 (6)	0.001 (6)	0.010 (5)
C25A	0.124 (10)	0.029 (6)	0.053 (6)	0.012 (6)	−0.004 (6)	0.016 (5)
C26A	0.076 (6)	0.033 (6)	0.043 (5)	0.014 (4)	−0.001 (4)	0.012 (4)
C41A	0.025 (3)	0.039 (5)	0.025 (4)	0.005 (3)	0.004 (3)	0.014 (4)
O42A	0.027 (2)	0.038 (4)	0.033 (3)	0.002 (2)	0.006 (2)	0.014 (3)
C43A	0.029 (4)	0.037 (5)	0.032 (4)	0.009 (3)	0.006 (3)	0.003 (4)
C44A	0.040 (4)	0.023 (4)	0.032 (4)	0.004 (3)	0.005 (3)	0.001 (3)
C45A	0.030 (4)	0.035 (5)	0.038 (4)	0.001 (3)	0.000 (3)	0.013 (4)
C46A	0.040 (4)	0.057 (7)	0.048 (5)	0.000 (4)	0.017 (4)	0.008 (5)
C51A	0.030 (4)	0.055 (6)	0.028 (4)	0.006 (4)	0.002 (3)	0.012 (4)
C52A	0.059 (6)	0.076 (9)	0.081 (8)	0.036 (6)	0.031 (5)	0.037 (7)
N1B	0.026 (3)	0.042 (4)	0.024 (3)	−0.003 (3)	0.005 (2)	0.014 (3)
N2B	0.026 (3)	0.036 (4)	0.029 (3)	0.002 (3)	0.010 (2)	0.007 (3)
O1B	0.033 (3)	0.040 (4)	0.029 (3)	0.006 (2)	0.004 (2)	0.013 (3)
O2B	0.026 (3)	0.051 (4)	0.044 (3)	−0.004 (2)	0.000 (2)	0.013 (3)
C1B	0.021 (3)	0.025 (4)	0.031 (4)	0.007 (3)	0.007 (3)	0.008 (3)
C2B	0.025 (3)	0.038 (5)	0.025 (4)	0.000 (3)	0.001 (3)	0.009 (3)
C3B	0.023 (3)	0.035 (5)	0.027 (4)	0.001 (3)	0.001 (3)	0.014 (3)
C4B	0.025 (3)	0.032 (5)	0.038 (4)	−0.002 (3)	−0.001 (3)	0.011 (4)
C5B	0.030 (4)	0.036 (5)	0.033 (4)	−0.007 (3)	0.000 (3)	0.017 (4)
C6B	0.029 (4)	0.037 (5)	0.037 (4)	0.002 (3)	−0.001 (3)	0.012 (4)
C11B	0.033 (4)	0.023 (4)	0.031 (4)	0.009 (3)	0.015 (3)	0.001 (3)
C12B	0.051 (5)	0.036 (6)	0.055 (6)	−0.004 (4)	0.011 (4)	0.019 (5)
C13B	0.071 (6)	0.042 (6)	0.069 (7)	−0.003 (5)	0.025 (5)	0.021 (6)
C14B	0.057 (6)	0.043 (7)	0.068 (7)	−0.013 (5)	0.018 (5)	−0.001 (5)
C15B	0.041 (5)	0.055 (7)	0.049 (6)	−0.005 (4)	0.009 (4)	−0.002 (5)
C16B	0.036 (4)	0.034 (5)	0.035 (4)	0.002 (4)	0.010 (3)	0.000 (4)
C21B	0.025 (3)	0.036 (5)	0.033 (4)	−0.001 (3)	0.004 (3)	0.019 (4)
C22B	0.027 (3)	0.043 (5)	0.028 (4)	0.006 (3)	0.006 (3)	0.010 (4)
C23B	0.038 (4)	0.049 (6)	0.041 (5)	0.007 (4)	0.009 (3)	0.015 (4)
C24B	0.026 (4)	0.058 (6)	0.049 (5)	0.007 (4)	0.002 (3)	0.027 (5)
C25B	0.034 (4)	0.053 (6)	0.047 (5)	−0.003 (4)	−0.005 (4)	0.028 (5)
C26B	0.022 (3)	0.039 (5)	0.039 (4)	−0.002 (3)	−0.002 (3)	0.015 (4)
C41B	0.027 (3)	0.045 (5)	0.034 (4)	0.002 (3)	0.007 (3)	0.020 (4)
O42B	0.048 (3)	0.040 (4)	0.032 (3)	−0.001 (3)	0.008 (2)	0.017 (3)
C43B	0.039 (4)	0.040 (6)	0.037 (5)	−0.005 (4)	0.000 (3)	0.016 (4)
C44B	0.047 (5)	0.057 (7)	0.069 (7)	0.006 (4)	0.010 (4)	0.044 (6)
C45B	0.050 (5)	0.046 (6)	0.050 (5)	0.014 (4)	0.024 (4)	0.022 (5)
C46B	0.084 (7)	0.072 (8)	0.035 (5)	−0.005 (6)	0.008 (5)	0.022 (5)
C51B	0.040 (4)	0.052 (6)	0.032 (4)	0.000 (4)	0.003 (3)	0.011 (4)
C52B	0.110 (9)	0.026 (6)	0.081 (8)	0.014 (6)	0.026 (7)	0.005 (6)
N1C	0.030 (3)	0.036 (4)	0.033 (4)	0.010 (3)	0.006 (3)	0.016 (3)
N2C	0.022 (3)	0.045 (4)	0.033 (4)	0.004 (3)	0.007 (2)	0.020 (3)
O1C	0.039 (3)	0.039 (4)	0.029 (3)	0.002 (2)	0.006 (2)	0.016 (3)
O2C	0.021 (3)	0.062 (4)	0.053 (4)	0.013 (2)	0.010 (2)	0.029 (3)
C1C	0.020 (3)	0.037 (5)	0.030 (4)	−0.003 (3)	0.008 (3)	0.013 (4)
C2C	0.018 (3)	0.042 (5)	0.035 (4)	0.007 (3)	0.005 (3)	0.022 (4)
C3C	0.028 (3)	0.036 (5)	0.028 (4)	0.001 (3)	0.002 (3)	0.016 (4)
C4C	0.027 (3)	0.035 (5)	0.036 (4)	0.000 (3)	0.006 (3)	0.020 (4)
C5C	0.035 (4)	0.044 (5)	0.030 (4)	0.011 (3)	0.007 (3)	0.017 (4)
C6C	0.035 (4)	0.033 (5)	0.052 (5)	0.008 (3)	−0.002 (3)	0.018 (4)
C11C	0.026 (3)	0.033 (5)	0.033 (4)	−0.001 (3)	0.008 (3)	0.008 (4)
C12C	0.051 (5)	0.036 (5)	0.041 (5)	0.001 (4)	0.011 (4)	0.013 (4)
C13C	0.075 (6)	0.029 (5)	0.056 (6)	0.010 (5)	0.023 (5)	0.006 (5)
C14C	0.068 (6)	0.062 (8)	0.069 (7)	0.029 (5)	0.030 (5)	0.040 (6)
C15C	0.042 (4)	0.057 (7)	0.052 (6)	0.015 (4)	0.007 (4)	0.026 (5)
C16C	0.037 (4)	0.039 (5)	0.042 (5)	0.013 (4)	0.012 (3)	0.016 (4)
C21C	0.025 (3)	0.045 (5)	0.023 (4)	0.009 (3)	0.011 (3)	0.011 (4)
C22C	0.031 (4)	0.047 (6)	0.036 (4)	0.001 (3)	0.005 (3)	0.022 (4)
C23C	0.037 (4)	0.047 (6)	0.043 (5)	0.002 (4)	0.007 (3)	0.016 (4)
C24C	0.023 (4)	0.051 (6)	0.046 (5)	−0.004 (4)	0.001 (3)	0.012 (4)
C25C	0.030 (4)	0.061 (7)	0.036 (5)	0.014 (4)	−0.002 (3)	0.015 (4)
C26C	0.037 (4)	0.044 (6)	0.033 (4)	0.014 (4)	0.005 (3)	0.017 (4)
C41C	0.025 (3)	0.044 (5)	0.033 (4)	0.006 (3)	0.009 (3)	0.021 (4)
O42C	0.045 (3)	0.038 (4)	0.037 (3)	0.007 (2)	0.009 (2)	0.019 (3)
C43C	0.043 (4)	0.048 (6)	0.029 (4)	0.013 (4)	0.005 (3)	0.013 (4)
C44C	0.051 (5)	0.064 (8)	0.039 (5)	−0.005 (5)	0.002 (4)	0.006 (5)
C45C	0.054 (5)	0.032 (5)	0.044 (5)	−0.004 (4)	0.015 (4)	0.013 (4)
C46C	0.085 (7)	0.079 (9)	0.054 (6)	0.018 (6)	0.020 (5)	0.040 (6)
C51C	0.032 (4)	0.055 (6)	0.048 (5)	0.009 (4)	0.003 (3)	0.031 (5)
C52C	0.147 (14)	0.056 (10)	0.137 (15)	−0.004 (9)	0.052 (11)	0.041 (10)
C1L	0.159 (16)	0.092 (14)	0.113 (14)	0.004 (11)	0.011 (11)	0.036 (11)
Cl12	0.143 (4)	0.113 (4)	0.222 (7)	0.025 (3)	0.083 (4)	0.051 (4)
Cl11	0.453 (17)	0.172 (8)	0.323 (14)	0.006 (9)	0.267 (14)	0.065 (8)
C2L	0.152 (17)	0.130 (18)	0.110 (14)	−0.059 (14)	−0.015 (12)	0.044 (13)
Cl21	0.194 (7)	0.130 (6)	0.307 (11)	0.028 (5)	−0.011 (6)	0.094 (7)
Cl22	0.208 (7)	0.219 (10)	0.205 (8)	−0.037 (6)	0.073 (6)	0.036 (7)

Geometric parameters (Å, º)

N1—C1	1.328 (10)	N2B—C4B	1.458 (10)
N1—C2	1.463 (10)	N2B—H2B	0.908 (14)
N1—H1	0.910 (14)	O1B—C1B	1.228 (8)
N2—C5	1.349 (9)	O2B—C5B	1.232 (9)
N2—C4	1.473 (9)	C1B—C11B	1.501 (11)
N2—H2	0.904 (14)	C2B—C21B	1.535 (9)
O1—C1	1.247 (9)	C2B—C3B	1.554 (9)
O2—C5	1.232 (9)	C2B—H2G	1.0000
C1—C11	1.500 (11)	C3B—C4B	1.535 (11)
C2—C21	1.525 (13)	C3B—C6B	1.546 (9)
C2—C3	1.537 (12)	C3B—H3B	1.0000
C2—H2D	1.0000	C4B—C41B	1.527 (10)
C3—C6	1.532 (11)	C4B—H4B	1.0000
C3—C4	1.578 (9)	C5B—C51B	1.486 (12)
C3—H3	1.0000	C6B—H6B1	0.9800
C4—C41	1.489 (11)	C6B—H6B2	0.9800
C4—H4	1.0000	C6B—H6B3	0.9800
C5—C51	1.518 (11)	C11B—C16B	1.396 (11)
C6—H6A	0.9800	C11B—C12B	1.405 (11)
C6—H6B	0.9800	C12B—C13B	1.367 (14)
C6—H6C	0.9800	C12B—H12B	0.9500
C11—C16	1.384 (12)	C13B—C14B	1.370 (15)
C11—C12	1.392 (11)	C13B—H13B	0.9500
C12—C13	1.380 (12)	C14B—C15B	1.398 (15)
C12—H12	0.9500	C14B—H14B	0.9500
C13—C14	1.370 (13)	C15B—C16B	1.387 (13)
C13—H13	0.9500	C15B—H15B	0.9500
C14—C15	1.356 (15)	C16B—H16B	0.9500
C14—H14	0.9500	C21B—C22B	1.389 (12)
C15—C16	1.390 (14)	C21B—C26B	1.404 (10)
C15—H15	0.9500	C22B—C23B	1.376 (11)
C16—H16	0.9500	C22B—H22B	0.9500
C21—C26	1.349 (14)	C23B—C24B	1.412 (12)
C21—C22	1.420 (14)	C23B—H23B	0.9500
C22—C23	1.405 (15)	C24B—C25B	1.347 (14)
C22—H22	0.9500	C24B—H24B	0.9500
C23—C24	1.354 (19)	C25B—C26B	1.400 (11)
C23—H23	0.9500	C25B—H25B	0.9500
C24—C25	1.334 (19)	C26B—H26B	0.9500
C24—H24	0.9500	C41B—C45B	1.344 (12)
C25—C26	1.459 (19)	C41B—O42B	1.357 (10)
C25—H25	0.9500	O42B—C43B	1.375 (9)
C26—H26	0.9500	C43B—C44B	1.356 (14)
C41—C45	1.352 (12)	C43B—C46B	1.468 (13)
C41—O42	1.366 (8)	C44B—C45B	1.430 (12)
O42—C43	1.383 (10)	C44B—H44B	0.9500
C43—C44	1.330 (12)	C45B—H45B	0.9500
C43—C46	1.507 (11)	C46B—H46G	0.9800
C44—C45	1.429 (11)	C46B—H46H	0.9800
C44—H44	0.9500	C46B—H46I	0.9800
C45—H45	0.9500	C51B—C52B	1.535 (15)
C46—H46A	0.9800	C51B—H51E	0.9900
C46—H46B	0.9800	C51B—H51F	0.9900
C46—H46C	0.9800	C52B—H52G	0.9800
C51—C52	1.513 (13)	C52B—H52H	0.9800
C51—H51A	0.9900	C52B—H52I	0.9800
C51—H51B	0.9900	N1C—C1C	1.336 (10)
C52—H52A	0.9800	N1C—C2C	1.472 (9)
C52—H52B	0.9800	N1C—H1C	0.909 (14)
C52—H52C	0.9800	N2C—C5C	1.357 (9)
N1A—C1A	1.344 (9)	N2C—C4C	1.463 (9)
N1A—C2A	1.478 (9)	N2C—H2C	0.912 (14)
N1A—H1A	0.903 (14)	O1C—C1C	1.246 (8)
N2A—C5A	1.348 (9)	O2C—C5C	1.234 (9)
N2A—C4A	1.483 (8)	C1C—C11C	1.500 (11)
N2A—H2A	0.908 (14)	C2C—C3C	1.523 (11)
O1A—C1A	1.242 (8)	C2C—C21C	1.537 (10)
O2A—C5A	1.242 (9)	C2C—H2F	1.0000
C1A—C11A	1.486 (10)	C3C—C6C	1.512 (10)
C2A—C21A	1.526 (11)	C3C—C4C	1.562 (10)
C2A—C3A	1.540 (11)	C3C—H3C	1.0000
C2A—H2E	1.0000	C4C—C41C	1.500 (11)
C3A—C6A	1.533 (9)	C4C—H4C	1.0000
C3A—C4A	1.557 (10)	C5C—C51C	1.516 (11)
C3A—H3A	1.0000	C6C—H6C1	0.9800
C4A—C41A	1.487 (11)	C6C—H6C2	0.9800
C4A—H4A	1.0000	C6C—H6C3	0.9800
C5A—C51A	1.523 (10)	C11C—C12C	1.379 (12)
C6A—H6A1	0.9800	C11C—C16C	1.383 (10)
C6A—H6A2	0.9800	C12C—C13C	1.425 (13)
C6A—H6A3	0.9800	C12C—H12C	0.9500
C11A—C12A	1.383 (11)	C13C—C14C	1.400 (14)
C11A—C16A	1.405 (11)	C13C—H13C	0.9500
C12A—C13A	1.388 (12)	C14C—C15C	1.378 (15)
C12A—H12A	0.9500	C14C—H14C	0.9500
C13A—C14A	1.372 (15)	C15C—C16C	1.385 (12)
C13A—H13A	0.9500	C15C—H15C	0.9500
C14A—C15A	1.387 (14)	C16C—H16C	0.9500
C14A—H14A	0.9500	C21C—C22C	1.387 (11)
C15A—C16A	1.381 (13)	C21C—C26C	1.389 (10)
C15A—H15A	0.9500	C22C—C23C	1.417 (11)
C16A—H16A	0.9500	C22C—H22C	0.9500
C21A—C26A	1.391 (11)	C23C—C24C	1.362 (11)
C21A—C22A	1.400 (12)	C23C—H23C	0.9500
C22A—C23A	1.386 (13)	C24C—C25C	1.373 (13)
C22A—H22A	0.9500	C24C—H24C	0.9500
C23A—C24A	1.381 (15)	C25C—C26C	1.395 (12)
C23A—H23A	0.9500	C25C—H25C	0.9500
C24A—C25A	1.401 (17)	C26C—H26C	0.9500
C24A—H24A	0.9500	C41C—C45C	1.338 (12)
C25A—C26A	1.385 (15)	C41C—O42C	1.384 (9)
C25A—H25A	0.9500	O42C—C43C	1.378 (10)
C26A—H26A	0.9500	C43C—C44C	1.351 (14)
C41A—O42A	1.367 (8)	C43C—C46C	1.476 (12)
C41A—C45A	1.368 (12)	C44C—C45C	1.445 (12)
O42A—C43A	1.398 (10)	C44C—H44C	0.9500
C43A—C44A	1.343 (11)	C45C—H45C	0.9500
C43A—C46A	1.502 (11)	C46C—H46J	0.9800
C44A—C45A	1.428 (11)	C46C—H46K	0.9800
C44A—H44A	0.9500	C46C—H46L	0.9800
C45A—H45A	0.9500	C51C—C52C	1.467 (18)
C46A—H46D	0.9800	C51C—H51G	0.9900
C46A—H46E	0.9800	C51C—H51H	0.9900
C46A—H46F	0.9800	C52C—H52J	0.9800
C51A—C52A	1.505 (13)	C52C—H52K	0.9800
C51A—H51C	0.9900	C52C—H52L	0.9800
C51A—H51D	0.9900	C1L—Cl12	1.627 (19)
C52A—H52D	0.9800	C1L—Cl11	1.66 (2)
C52A—H52E	0.9800	C1L—H1L1	0.9900
C52A—H52F	0.9800	C1L—H1L2	0.9900
N1B—C1B	1.346 (9)	C2L—Cl22	1.68 (2)
N1B—C2B	1.476 (10)	C2L—Cl21	1.72 (2)
N1B—H1B	0.909 (14)	C2L—H2L1	0.9900
N2B—C5B	1.348 (9)	C2L—H2L2	0.9900
C1—N1—C2	122.7 (6)	O1B—C1B—N1B	122.6 (7)
C1—N1—H1	117 (5)	O1B—C1B—C11B	121.1 (6)
C2—N1—H1	119 (5)	N1B—C1B—C11B	116.3 (6)
C5—N2—C4	120.8 (6)	N1B—C2B—C21B	109.2 (6)
C5—N2—H2	116 (5)	N1B—C2B—C3B	109.2 (5)
C4—N2—H2	121 (5)	C21B—C2B—C3B	113.5 (6)
O1—C1—N1	122.5 (7)	N1B—C2B—H2G	108.3
O1—C1—C11	119.6 (7)	C21B—C2B—H2G	108.3
N1—C1—C11	117.9 (6)	C3B—C2B—H2G	108.3
N1—C2—C21	111.4 (7)	C4B—C3B—C6B	111.5 (6)
N1—C2—C3	111.2 (6)	C4B—C3B—C2B	110.4 (5)
C21—C2—C3	112.0 (7)	C6B—C3B—C2B	111.0 (6)
N1—C2—H2D	107.3	C4B—C3B—H3B	107.9
C21—C2—H2D	107.3	C6B—C3B—H3B	107.9
C3—C2—H2D	107.3	C2B—C3B—H3B	107.9
C6—C3—C2	111.8 (6)	N2B—C4B—C41B	109.1 (7)
C6—C3—C4	111.0 (6)	N2B—C4B—C3B	113.2 (6)
C2—C3—C4	110.4 (6)	C41B—C4B—C3B	110.6 (6)
C6—C3—H3	107.8	N2B—C4B—H4B	107.9
C2—C3—H3	107.8	C41B—C4B—H4B	107.9
C4—C3—H3	107.8	C3B—C4B—H4B	107.9
N2—C4—C41	110.6 (6)	O2B—C5B—N2B	122.5 (8)
N2—C4—C3	110.3 (5)	O2B—C5B—C51B	121.4 (7)
C41—C4—C3	112.3 (6)	N2B—C5B—C51B	116.1 (7)
N2—C4—H4	107.8	C3B—C6B—H6B1	109.5
C41—C4—H4	107.8	C3B—C6B—H6B2	109.5
C3—C4—H4	107.8	H6B1—C6B—H6B2	109.5
O2—C5—N2	122.5 (7)	C3B—C6B—H6B3	109.5
O2—C5—C51	121.6 (6)	H6B1—C6B—H6B3	109.5
N2—C5—C51	115.8 (6)	H6B2—C6B—H6B3	109.5
C3—C6—H6A	109.5	C16B—C11B—C12B	119.2 (8)
C3—C6—H6B	109.5	C16B—C11B—C1B	122.6 (7)
H6A—C6—H6B	109.5	C12B—C11B—C1B	118.2 (7)
C3—C6—H6C	109.5	C13B—C12B—C11B	119.9 (9)
H6A—C6—H6C	109.5	C13B—C12B—H12B	120.1
H6B—C6—H6C	109.5	C11B—C12B—H12B	120.1
C16—C11—C12	116.8 (8)	C12B—C13B—C14B	121.2 (9)
C16—C11—C1	118.7 (7)	C12B—C13B—H13B	119.4
C12—C11—C1	124.5 (7)	C14B—C13B—H13B	119.4
C13—C12—C11	120.8 (8)	C13B—C14B—C15B	120.1 (9)
C13—C12—H12	119.6	C13B—C14B—H14B	120.0
C11—C12—H12	119.6	C15B—C14B—H14B	120.0
C14—C13—C12	121.5 (9)	C16B—C15B—C14B	119.5 (9)
C14—C13—H13	119.2	C16B—C15B—H15B	120.3
C12—C13—H13	119.2	C14B—C15B—H15B	120.3
C15—C14—C13	118.4 (9)	C15B—C16B—C11B	120.2 (8)
C15—C14—H14	120.8	C15B—C16B—H16B	119.9
C13—C14—H14	120.8	C11B—C16B—H16B	119.9
C14—C15—C16	121.0 (9)	C22B—C21B—C26B	118.8 (7)
C14—C15—H15	119.5	C22B—C21B—C2B	121.7 (6)
C16—C15—H15	119.5	C26B—C21B—C2B	119.4 (7)
C11—C16—C15	121.4 (9)	C23B—C22B—C21B	121.9 (7)
C11—C16—H16	119.3	C23B—C22B—H22B	119.1
C15—C16—H16	119.3	C21B—C22B—H22B	119.1
C26—C21—C22	116.8 (10)	C22B—C23B—C24B	118.4 (8)
C26—C21—C2	122.7 (10)	C22B—C23B—H23B	120.8
C22—C21—C2	120.4 (8)	C24B—C23B—H23B	120.8
C23—C22—C21	122.8 (10)	C25B—C24B—C23B	120.5 (7)
C23—C22—H22	118.6	C25B—C24B—H24B	119.7
C21—C22—H22	118.6	C23B—C24B—H24B	119.7
C24—C23—C22	118.6 (12)	C24B—C25B—C26B	121.4 (8)
C24—C23—H23	120.7	C24B—C25B—H25B	119.3
C22—C23—H23	120.7	C26B—C25B—H25B	119.3
C25—C24—C23	120.6 (12)	C25B—C26B—C21B	118.9 (8)
C25—C24—H24	119.7	C25B—C26B—H26B	120.5
C23—C24—H24	119.7	C21B—C26B—H26B	120.5
C24—C25—C26	121.6 (11)	C45B—C41B—O42B	110.1 (6)
C24—C25—H25	119.2	C45B—C41B—C4B	133.5 (8)
C26—C25—H25	119.2	O42B—C41B—C4B	116.3 (7)
C21—C26—C25	119.5 (13)	C41B—O42B—C43B	108.1 (7)
C21—C26—H26	120.3	C44B—C43B—O42B	108.0 (7)
C25—C26—H26	120.3	C44B—C43B—C46B	134.7 (8)
C45—C41—O42	109.5 (7)	O42B—C43B—C46B	117.2 (8)
C45—C41—C4	133.5 (7)	C43B—C44B—C45B	107.6 (8)
O42—C41—C4	117.0 (7)	C43B—C44B—H44B	126.2
C41—O42—C43	106.9 (6)	C45B—C44B—H44B	126.2
C44—C43—O42	109.9 (7)	C41B—C45B—C44B	106.1 (8)
C44—C43—C46	134.8 (9)	C41B—C45B—H45B	127.0
O42—C43—C46	115.2 (8)	C44B—C45B—H45B	127.0
C43—C44—C45	106.9 (8)	C43B—C46B—H46G	109.5
C43—C44—H44	126.5	C43B—C46B—H46H	109.5
C45—C44—H44	126.5	H46G—C46B—H46H	109.5
C41—C45—C44	106.8 (7)	C43B—C46B—H46I	109.5
C41—C45—H45	126.6	H46G—C46B—H46I	109.5
C44—C45—H45	126.6	H46H—C46B—H46I	109.5
C43—C46—H46A	109.5	C5B—C51B—C52B	110.2 (8)
C43—C46—H46B	109.5	C5B—C51B—H51E	109.6
H46A—C46—H46B	109.5	C52B—C51B—H51E	109.6
C43—C46—H46C	109.5	C5B—C51B—H51F	109.6
H46A—C46—H46C	109.5	C52B—C51B—H51F	109.6
H46B—C46—H46C	109.5	H51E—C51B—H51F	108.1
C52—C51—C5	112.3 (8)	C51B—C52B—H52G	109.5
C52—C51—H51A	109.1	C51B—C52B—H52H	109.5
C5—C51—H51A	109.1	H52G—C52B—H52H	109.5
C52—C51—H51B	109.1	C51B—C52B—H52I	109.5
C5—C51—H51B	109.1	H52G—C52B—H52I	109.5
H51A—C51—H51B	107.9	H52H—C52B—H52I	109.5
C51—C52—H52A	109.5	C1C—N1C—C2C	121.9 (5)
C51—C52—H52B	109.5	C1C—N1C—H1C	120 (6)
H52A—C52—H52B	109.5	C2C—N1C—H1C	116 (5)
C51—C52—H52C	109.5	C5C—N2C—C4C	121.7 (6)
H52A—C52—H52C	109.5	C5C—N2C—H2C	122 (5)
H52B—C52—H52C	109.5	C4C—N2C—H2C	116 (5)
C1A—N1A—C2A	121.3 (6)	O1C—C1C—N1C	121.5 (7)
C1A—N1A—H1A	123 (5)	O1C—C1C—C11C	121.4 (7)
C2A—N1A—H1A	116 (5)	N1C—C1C—C11C	117.1 (6)
C5A—N2A—C4A	120.6 (6)	N1C—C2C—C3C	109.2 (5)
C5A—N2A—H2A	115 (5)	N1C—C2C—C21C	109.3 (7)
C4A—N2A—H2A	124 (5)	C3C—C2C—C21C	114.5 (6)
O1A—C1A—N1A	121.9 (6)	N1C—C2C—H2F	107.8
O1A—C1A—C11A	120.9 (6)	C3C—C2C—H2F	107.8
N1A—C1A—C11A	117.2 (6)	C21C—C2C—H2F	107.8
N1A—C2A—C21A	110.4 (6)	C6C—C3C—C2C	111.4 (6)
N1A—C2A—C3A	111.0 (5)	C6C—C3C—C4C	111.8 (7)
C21A—C2A—C3A	112.9 (6)	C2C—C3C—C4C	111.5 (5)
N1A—C2A—H2E	107.4	C6C—C3C—H3C	107.3
C21A—C2A—H2E	107.4	C2C—C3C—H3C	107.3
C3A—C2A—H2E	107.4	C4C—C3C—H3C	107.3
C6A—C3A—C2A	112.5 (6)	N2C—C4C—C41C	109.3 (6)
C6A—C3A—C4A	111.3 (6)	N2C—C4C—C3C	111.4 (6)
C2A—C3A—C4A	109.6 (5)	C41C—C4C—C3C	111.1 (5)
C6A—C3A—H3A	107.7	N2C—C4C—H4C	108.3
C2A—C3A—H3A	107.7	C41C—C4C—H4C	108.3
C4A—C3A—H3A	107.7	C3C—C4C—H4C	108.3
N2A—C4A—C41A	110.5 (6)	O2C—C5C—N2C	122.8 (7)
N2A—C4A—C3A	109.7 (6)	O2C—C5C—C51C	121.9 (6)
C41A—C4A—C3A	112.8 (5)	N2C—C5C—C51C	115.3 (6)
N2A—C4A—H4A	107.9	C3C—C6C—H6C1	109.5
C41A—C4A—H4A	107.9	C3C—C6C—H6C2	109.5
C3A—C4A—H4A	107.9	H6C1—C6C—H6C2	109.5
O2A—C5A—N2A	123.5 (7)	C3C—C6C—H6C3	109.5
O2A—C5A—C51A	121.6 (6)	H6C1—C6C—H6C3	109.5
N2A—C5A—C51A	114.8 (6)	H6C2—C6C—H6C3	109.5
C3A—C6A—H6A1	109.5	C12C—C11C—C16C	119.9 (8)
C3A—C6A—H6A2	109.5	C12C—C11C—C1C	118.1 (7)
H6A1—C6A—H6A2	109.5	C16C—C11C—C1C	121.9 (7)
C3A—C6A—H6A3	109.5	C11C—C12C—C13C	120.0 (8)
H6A1—C6A—H6A3	109.5	C11C—C12C—H12C	120.0
H6A2—C6A—H6A3	109.5	C13C—C12C—H12C	120.0
C12A—C11A—C16A	117.1 (7)	C14C—C13C—C12C	118.6 (9)
C12A—C11A—C1A	124.8 (7)	C14C—C13C—H13C	120.7
C16A—C11A—C1A	118.0 (7)	C12C—C13C—H13C	120.7
C11A—C12A—C13A	122.0 (8)	C15C—C14C—C13C	120.5 (9)
C11A—C12A—H12A	119.0	C15C—C14C—H14C	119.7
C13A—C12A—H12A	119.0	C13C—C14C—H14C	119.7
C14A—C13A—C12A	119.8 (9)	C14C—C15C—C16C	120.0 (8)
C14A—C13A—H13A	120.1	C14C—C15C—H15C	120.0
C12A—C13A—H13A	120.1	C16C—C15C—H15C	120.0
C13A—C14A—C15A	119.8 (9)	C11C—C16C—C15C	121.0 (8)
C13A—C14A—H14A	120.1	C11C—C16C—H16C	119.5
C15A—C14A—H14A	120.1	C15C—C16C—H16C	119.5
C16A—C15A—C14A	120.1 (9)	C22C—C21C—C26C	119.5 (7)
C16A—C15A—H15A	120.0	C22C—C21C—C2C	120.0 (6)
C14A—C15A—H15A	120.0	C26C—C21C—C2C	120.4 (7)
C15A—C16A—C11A	121.2 (8)	C21C—C22C—C23C	119.9 (7)
C15A—C16A—H16A	119.4	C21C—C22C—H22C	120.0
C11A—C16A—H16A	119.4	C23C—C22C—H22C	120.0
C26A—C21A—C22A	118.3 (8)	C24C—C23C—C22C	119.6 (8)
C26A—C21A—C2A	120.8 (8)	C24C—C23C—H23C	120.2
C22A—C21A—C2A	120.8 (7)	C22C—C23C—H23C	120.2
C23A—C22A—C21A	121.5 (8)	C23C—C24C—C25C	120.7 (7)
C23A—C22A—H22A	119.3	C23C—C24C—H24C	119.6
C21A—C22A—H22A	119.3	C25C—C24C—H24C	119.6
C24A—C23A—C22A	119.2 (10)	C24C—C25C—C26C	120.5 (7)
C24A—C23A—H23A	120.4	C24C—C25C—H25C	119.7
C22A—C23A—H23A	120.4	C26C—C25C—H25C	119.7
C23A—C24A—C25A	120.6 (10)	C21C—C26C—C25C	119.7 (8)
C23A—C24A—H24A	119.7	C21C—C26C—H26C	120.2
C25A—C24A—H24A	119.7	C25C—C26C—H26C	120.2
C26A—C25A—C24A	119.3 (9)	C45C—C41C—O42C	109.2 (7)
C26A—C25A—H25A	120.3	C45C—C41C—C4C	134.7 (7)
C24A—C25A—H25A	120.3	O42C—C41C—C4C	115.9 (7)
C25A—C26A—C21A	121.1 (10)	C43C—O42C—C41C	107.8 (7)
C25A—C26A—H26A	119.5	C44C—C43C—O42C	108.9 (7)
C21A—C26A—H26A	119.5	C44C—C43C—C46C	134.5 (10)
O42A—C41A—C45A	109.4 (7)	O42C—C43C—C46C	116.6 (9)
O42A—C41A—C4A	116.6 (6)	C43C—C44C—C45C	106.9 (9)
C45A—C41A—C4A	134.0 (7)	C43C—C44C—H44C	126.6
C41A—O42A—C43A	106.8 (6)	C45C—C44C—H44C	126.6
C44A—C43A—O42A	109.9 (6)	C41C—C45C—C44C	107.2 (8)
C44A—C43A—C46A	134.2 (8)	C41C—C45C—H45C	126.4
O42A—C43A—C46A	115.9 (7)	C44C—C45C—H45C	126.4
C43A—C44A—C45A	106.8 (7)	C43C—C46C—H46J	109.5
C43A—C44A—H44A	126.6	C43C—C46C—H46K	109.5
C45A—C44A—H44A	126.6	H46J—C46C—H46K	109.5
C41A—C45A—C44A	107.1 (7)	C43C—C46C—H46L	109.5
C41A—C45A—H45A	126.4	H46J—C46C—H46L	109.5
C44A—C45A—H45A	126.4	H46K—C46C—H46L	109.5
C43A—C46A—H46D	109.5	C52C—C51C—C5C	110.9 (9)
C43A—C46A—H46E	109.5	C52C—C51C—H51G	109.5
H46D—C46A—H46E	109.5	C5C—C51C—H51G	109.5
C43A—C46A—H46F	109.5	C52C—C51C—H51H	109.5
H46D—C46A—H46F	109.5	C5C—C51C—H51H	109.5
H46E—C46A—H46F	109.5	H51G—C51C—H51H	108.0
C52A—C51A—C5A	113.1 (8)	C51C—C52C—H52J	109.5
C52A—C51A—H51C	109.0	C51C—C52C—H52K	109.5
C5A—C51A—H51C	109.0	H52J—C52C—H52K	109.5
C52A—C51A—H51D	109.0	C51C—C52C—H52L	109.5
C5A—C51A—H51D	109.0	H52J—C52C—H52L	109.5
H51C—C51A—H51D	107.8	H52K—C52C—H52L	109.5
C51A—C52A—H52D	109.5	Cl12—C1L—Cl11	113.7 (12)
C51A—C52A—H52E	109.5	Cl12—C1L—H1L1	108.8
H52D—C52A—H52E	109.5	Cl11—C1L—H1L1	108.8
C51A—C52A—H52F	109.5	Cl12—C1L—H1L2	108.8
H52D—C52A—H52F	109.5	Cl11—C1L—H1L2	108.8
H52E—C52A—H52F	109.5	H1L1—C1L—H1L2	107.7
C1B—N1B—C2B	119.8 (6)	Cl22—C2L—Cl21	110.6 (11)
C1B—N1B—H1B	133 (5)	Cl22—C2L—H2L1	109.5
C2B—N1B—H1B	105 (5)	Cl21—C2L—H2L1	109.5
C5B—N2B—C4B	122.0 (6)	Cl22—C2L—H2L2	109.5
C5B—N2B—H2B	102 (5)	Cl21—C2L—H2L2	109.5
C4B—N2B—H2B	130 (5)	H2L1—C2L—H2L2	108.1
C2—N1—C1—O1	5.2 (13)	C2B—N1B—C1B—O1B	−4.7 (10)
C2—N1—C1—C11	−173.8 (8)	C2B—N1B—C1B—C11B	175.4 (6)
C1—N1—C2—C21	−122.9 (8)	C1B—N1B—C2B—C21B	−80.6 (8)
C1—N1—C2—C3	111.4 (8)	C1B—N1B—C2B—C3B	154.9 (6)
N1—C2—C3—C6	−45.7 (8)	N1B—C2B—C3B—C4B	−177.4 (6)
C21—C2—C3—C6	−171.1 (6)	C21B—C2B—C3B—C4B	60.6 (9)
N1—C2—C3—C4	−169.8 (6)	N1B—C2B—C3B—C6B	−53.2 (8)
C21—C2—C3—C4	64.8 (8)	C21B—C2B—C3B—C6B	−175.2 (7)
C5—N2—C4—C41	82.8 (8)	C5B—N2B—C4B—C41B	91.5 (8)
C5—N2—C4—C3	−152.3 (7)	C5B—N2B—C4B—C3B	−144.9 (6)
C6—C3—C4—N2	−49.9 (8)	C6B—C3B—C4B—N2B	−62.7 (7)
C2—C3—C4—N2	74.6 (8)	C2B—C3B—C4B—N2B	61.2 (8)
C6—C3—C4—C41	73.9 (8)	C6B—C3B—C4B—C41B	60.1 (8)
C2—C3—C4—C41	−161.5 (6)	C2B—C3B—C4B—C41B	−176.0 (6)
C4—N2—C5—O2	10.1 (11)	C4B—N2B—C5B—O2B	7.5 (11)
C4—N2—C5—C51	−172.1 (7)	C4B—N2B—C5B—C51B	−172.8 (7)
O1—C1—C11—C16	6.1 (13)	O1B—C1B—C11B—C16B	−153.2 (7)
N1—C1—C11—C16	−174.9 (9)	N1B—C1B—C11B—C16B	26.7 (10)
O1—C1—C11—C12	−173.6 (9)	O1B—C1B—C11B—C12B	25.3 (10)
N1—C1—C11—C12	5.4 (12)	N1B—C1B—C11B—C12B	−154.8 (7)
C16—C11—C12—C13	0.1 (14)	C16B—C11B—C12B—C13B	0.2 (13)
C1—C11—C12—C13	179.8 (10)	C1B—C11B—C12B—C13B	−178.3 (8)
C11—C12—C13—C14	−0.2 (17)	C11B—C12B—C13B—C14B	−0.8 (15)
C12—C13—C14—C15	1.0 (18)	C12B—C13B—C14B—C15B	0.7 (16)
C13—C14—C15—C16	−1.7 (19)	C13B—C14B—C15B—C16B	0.0 (15)
C12—C11—C16—C15	−0.7 (16)	C14B—C15B—C16B—C11B	−0.6 (13)
C1—C11—C16—C15	179.5 (11)	C12B—C11B—C16B—C15B	0.5 (12)
C14—C15—C16—C11	2 (2)	C1B—C11B—C16B—C15B	179.0 (7)
N1—C2—C21—C26	114.9 (9)	N1B—C2B—C21B—C22B	−44.5 (9)
C3—C2—C21—C26	−119.8 (9)	C3B—C2B—C21B—C22B	77.5 (9)
N1—C2—C21—C22	−65.3 (10)	N1B—C2B—C21B—C26B	133.1 (7)
C3—C2—C21—C22	60.0 (10)	C3B—C2B—C21B—C26B	−105.0 (8)
C26—C21—C22—C23	0.1 (15)	C26B—C21B—C22B—C23B	−0.7 (11)
C2—C21—C22—C23	−179.7 (10)	C2B—C21B—C22B—C23B	176.9 (7)
C21—C22—C23—C24	−0.7 (18)	C21B—C22B—C23B—C24B	−0.1 (12)
C22—C23—C24—C25	−0.7 (18)	C22B—C23B—C24B—C25B	0.1 (13)
C23—C24—C25—C26	2.6 (19)	C23B—C24B—C25B—C26B	0.8 (13)
C22—C21—C26—C25	1.7 (14)	C24B—C25B—C26B—C21B	−1.6 (12)
C2—C21—C26—C25	−178.5 (9)	C22B—C21B—C26B—C25B	1.5 (11)
C24—C25—C26—C21	−3.2 (17)	C2B—C21B—C26B—C25B	−176.1 (7)
N2—C4—C41—C45	30.4 (10)	N2B—C4B—C41B—C45B	10.4 (11)
C3—C4—C41—C45	−93.3 (9)	C3B—C4B—C41B—C45B	−114.8 (10)
N2—C4—C41—O42	−149.0 (5)	N2B—C4B—C41B—O42B	−174.1 (6)
C3—C4—C41—O42	87.3 (7)	C3B—C4B—C41B—O42B	60.8 (8)
C45—C41—O42—C43	−0.5 (7)	C45B—C41B—O42B—C43B	−1.0 (8)
C4—C41—O42—C43	179.1 (5)	C4B—C41B—O42B—C43B	−177.6 (6)
C41—O42—C43—C44	0.7 (8)	C41B—O42B—C43B—C44B	1.7 (8)
C41—O42—C43—C46	−176.5 (6)	C41B—O42B—C43B—C46B	−177.3 (7)
O42—C43—C44—C45	−0.5 (8)	O42B—C43B—C44B—C45B	−1.7 (9)
C46—C43—C44—C45	175.8 (8)	C46B—C43B—C44B—C45B	177.0 (10)
O42—C41—C45—C44	0.2 (8)	O42B—C41B—C45B—C44B	0.0 (9)
C4—C41—C45—C44	−179.3 (7)	C4B—C41B—C45B—C44B	175.8 (8)
C43—C44—C45—C41	0.2 (8)	C43B—C44B—C45B—C41B	1.0 (10)
O2—C5—C51—C52	63.6 (10)	O2B—C5B—C51B—C52B	−61.6 (10)
N2—C5—C51—C52	−114.3 (8)	N2B—C5B—C51B—C52B	118.8 (8)
C2A—N1A—C1A—O1A	−8.5 (11)	C2C—N1C—C1C—O1C	4.8 (11)
C2A—N1A—C1A—C11A	171.5 (6)	C2C—N1C—C1C—C11C	−175.8 (6)
C1A—N1A—C2A—C21A	124.2 (7)	C1C—N1C—C2C—C3C	−154.9 (6)
C1A—N1A—C2A—C3A	−109.9 (7)	C1C—N1C—C2C—C21C	79.1 (8)
N1A—C2A—C3A—C6A	43.9 (8)	N1C—C2C—C3C—C6C	53.1 (8)
C21A—C2A—C3A—C6A	168.4 (6)	C21C—C2C—C3C—C6C	176.1 (6)
N1A—C2A—C3A—C4A	168.4 (6)	N1C—C2C—C3C—C4C	178.8 (6)
C21A—C2A—C3A—C4A	−67.1 (7)	C21C—C2C—C3C—C4C	−58.2 (8)
C5A—N2A—C4A—C41A	−90.3 (8)	C5C—N2C—C4C—C41C	−89.3 (8)
C5A—N2A—C4A—C3A	144.7 (7)	C5C—N2C—C4C—C3C	147.5 (7)
C6A—C3A—C4A—N2A	52.2 (8)	C6C—C3C—C4C—N2C	62.6 (8)
C2A—C3A—C4A—N2A	−73.0 (7)	C2C—C3C—C4C—N2C	−62.9 (8)
C6A—C3A—C4A—C41A	−71.5 (7)	C6C—C3C—C4C—C41C	−59.6 (8)
C2A—C3A—C4A—C41A	163.4 (6)	C2C—C3C—C4C—C41C	174.9 (6)
C4A—N2A—C5A—O2A	−8.6 (12)	C4C—N2C—C5C—O2C	−9.8 (12)
C4A—N2A—C5A—C51A	174.3 (7)	C4C—N2C—C5C—C51C	170.3 (7)
O1A—C1A—C11A—C12A	156.7 (8)	O1C—C1C—C11C—C12C	−25.7 (11)
N1A—C1A—C11A—C12A	−23.3 (11)	N1C—C1C—C11C—C12C	154.9 (7)
O1A—C1A—C11A—C16A	−18.9 (11)	O1C—C1C—C11C—C16C	153.7 (7)
N1A—C1A—C11A—C16A	161.1 (7)	N1C—C1C—C11C—C16C	−25.7 (10)
C16A—C11A—C12A—C13A	0.2 (12)	C16C—C11C—C12C—C13C	−0.1 (12)
C1A—C11A—C12A—C13A	−175.4 (8)	C1C—C11C—C12C—C13C	179.4 (8)
C11A—C12A—C13A—C14A	−0.6 (14)	C11C—C12C—C13C—C14C	1.7 (14)
C12A—C13A—C14A—C15A	1.4 (15)	C12C—C13C—C14C—C15C	−2.6 (15)
C13A—C14A—C15A—C16A	−1.8 (16)	C13C—C14C—C15C—C16C	1.7 (15)
C14A—C15A—C16A—C11A	1.3 (15)	C12C—C11C—C16C—C15C	−0.8 (12)
C12A—C11A—C16A—C15A	−0.5 (13)	C1C—C11C—C16C—C15C	179.8 (8)
C1A—C11A—C16A—C15A	175.4 (8)	C14C—C15C—C16C—C11C	0.0 (13)
N1A—C2A—C21A—C26A	−119.0 (8)	N1C—C2C—C21C—C22C	45.3 (9)
C3A—C2A—C21A—C26A	116.1 (8)	C3C—C2C—C21C—C22C	−77.6 (9)
N1A—C2A—C21A—C22A	57.7 (10)	N1C—C2C—C21C—C26C	−132.5 (7)
C3A—C2A—C21A—C22A	−67.2 (10)	C3C—C2C—C21C—C26C	104.6 (8)
C26A—C21A—C22A—C23A	−1.1 (14)	C26C—C21C—C22C—C23C	0.4 (12)
C2A—C21A—C22A—C23A	−177.9 (9)	C2C—C21C—C22C—C23C	−177.4 (8)
C21A—C22A—C23A—C24A	0.4 (16)	C21C—C22C—C23C—C24C	0.4 (13)
C22A—C23A—C24A—C25A	0.6 (17)	C22C—C23C—C24C—C25C	0.2 (14)
C23A—C24A—C25A—C26A	−0.8 (16)	C23C—C24C—C25C—C26C	−1.7 (14)
C24A—C25A—C26A—C21A	0.0 (16)	C22C—C21C—C26C—C25C	−1.9 (12)
C22A—C21A—C26A—C25A	0.9 (14)	C2C—C21C—C26C—C25C	175.9 (8)
C2A—C21A—C26A—C25A	177.7 (9)	C24C—C25C—C26C—C21C	2.6 (13)
N2A—C4A—C41A—O42A	147.9 (5)	N2C—C4C—C41C—C45C	−12.9 (11)
C3A—C4A—C41A—O42A	−88.9 (7)	C3C—C4C—C41C—C45C	110.4 (10)
N2A—C4A—C41A—C45A	−31.6 (10)	N2C—C4C—C41C—O42C	172.7 (5)
C3A—C4A—C41A—C45A	91.6 (9)	C3C—C4C—C41C—O42C	−63.9 (7)
C45A—C41A—O42A—C43A	−0.1 (7)	C45C—C41C—O42C—C43C	0.3 (8)
C4A—C41A—O42A—C43A	−179.7 (6)	C4C—C41C—O42C—C43C	176.0 (6)
C41A—O42A—C43A—C44A	−0.9 (8)	C41C—O42C—C43C—C44C	−1.2 (8)
C41A—O42A—C43A—C46A	178.7 (6)	C41C—O42C—C43C—C46C	177.8 (7)
O42A—C43A—C44A—C45A	1.5 (8)	O42C—C43C—C44C—C45C	1.6 (10)
C46A—C43A—C44A—C45A	−178.0 (8)	C46C—C43C—C44C—C45C	−177.2 (10)
O42A—C41A—C45A—C44A	1.0 (8)	O42C—C41C—C45C—C44C	0.7 (9)
C4A—C41A—C45A—C44A	−179.5 (7)	C4C—C41C—C45C—C44C	−173.9 (8)
C43A—C44A—C45A—C41A	−1.5 (8)	C43C—C44C—C45C—C41C	−1.4 (10)
O2A—C5A—C51A—C52A	−59.9 (11)	O2C—C5C—C51C—C52C	75.4 (12)
N2A—C5A—C51A—C52A	117.3 (8)	N2C—C5C—C51C—C52C	−104.7 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2B^i	0.91 (1)	2.31 (3)	3.194 (8)	164 (7)
N2—H2···O1B	0.90 (1)	2.16 (5)	2.947 (9)	145 (7)
N1A—H1A···O2C^i	0.90 (1)	2.31 (3)	3.195 (7)	166 (8)
N2A—H2A···O1C	0.91 (1)	2.08 (5)	2.898 (8)	149 (7)
N1B—H1B···O2A	0.91 (1)	2.13 (3)	3.008 (8)	162 (7)
N2B—H2B···O1	0.91 (1)	2.18 (3)	3.040 (8)	158 (7)
N1C—H1C···O2^ii	0.91 (1)	2.15 (3)	3.036 (8)	165 (7)
N2C—H2C···O1A	0.91 (1)	2.12 (4)	2.983 (8)	157 (8)

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