Two novel poly­morphic forms of iron-chelating agent deferiprone

Thalassemia is a genetic blood disorder requiring life-long blood transfusions. This process often results in iron overload and can be treated by an iron-chelating agent, like deferiprone (3-hy­droxy-1,2-di­methyl­pyridin-4-one), C₇H₉NO₂, in an oral formulation. The first crystal structure of deferiprone, (Ia), was reported in 1988 [Nelson et al. (1988). Can. J. Chem. 66, 123–131]. In the present study, two novel poly­morphic forms, (Ib) and (Ic), of deferiprone were identified concomitantly with poly­morph (Ia) during the crystallization experiments. Polymorph (Ia) was redetermined at low temperature for com­parison of the structural features and lattice energy values with polymorphs (Ib) and (Ic). Polymorph (Ia) crystallized in the ortho­rhom­bic space group Pbca, whereas both poly­morphs (Ib) and (Ic) crystallized in the monoclinic space group P2₁/c. The asymmetric units of (Ia) and (Ib) contain one deferiprone mol­ecule, while poly­morph (Ic) has three crystallographically independent mol­ecules (A, B and C). All three poly­morphs have similar hydrogen-bonding features, such as an R₂²(10) dimer formed by O—H...O hydrogen bonds, an R₄³(20) tetra­mer formed by C—H...O hydrogen bonds and π–π inter­actions, but the poly­morphs differ in their mol­ecular arrangements in the solid state and are classified as packing poly­morphs. O—H...O and C—H...O hydrogen bonds lead to the formation of two-dimensional hydrogen-bonded parallel sheets which are inter­linked by π–π stacking inter­actions. In the three-dimensional crystal packing, the deferiprone mol­ecules were aggregated as corrugated sheets in polymorphs (Ia) and (Ic), whereas in polymorph (Ib), they were aggregated as a square-grid network. The characteristic crystalline peaks of poly­morphs (Ia), (Ib) and (Ic) were established through powder X-ray diffraction analysis. The Rietveld analysis was also performed to estimate the contribution of the poly­morphs to the bulk material.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) for (Ia), (Ib); SHELXL2018 (Sheldrick, 2015b) for (Ic). For all structures, molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2016).

3-Hydroxy-1,2-dimethylpyridin-4-one (Ia)

Crystal data

C7H9NO2	Dx = 1.454 Mg m^−3
Mr = 139.15	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9965 reflections
a = 7.185 (3) Å	θ = 3.0–30.5°
b = 12.917 (6) Å	µ = 0.11 mm^−1
c = 13.697 (6) Å	T = 100 K
V = 1271.1 (9) Å^3	Needle, colorless
Z = 8	0.28 × 0.14 × 0.12 mm
F(000) = 592

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	1824 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 30.5°, θmin = 3.0°
Tmin = 0.648, Tmax = 0.746	h = −10→10
12849 measured reflections	k = −16→18
1936 independent reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0606P)^2 + 0.6668P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
1936 reflections	Δρmax = 0.47 e Å^−3
97 parameters	Δρmin = −0.21 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C1	0.41667 (13)	0.44973 (7)	0.21598 (7)	0.00968 (19)
C2	0.42391 (13)	0.46427 (7)	0.31553 (7)	0.00973 (19)
C3	0.36789 (13)	0.38535 (7)	0.38371 (7)	0.01010 (19)
C4	0.30830 (14)	0.29075 (7)	0.34053 (7)	0.01154 (19)
H4	0.269639	0.235180	0.381184	0.014*
C5	0.30593 (14)	0.27876 (7)	0.24132 (7)	0.0118 (2)
H5	0.266703	0.214490	0.214600	0.014*
C6	0.35240 (15)	0.33722 (8)	0.07432 (7)	0.0151 (2)
H6A	0.316186	0.265298	0.061778	0.023*
H6B	0.475850	0.350139	0.046435	0.023*
H6C	0.261606	0.383954	0.044174	0.023*
C7	0.46748 (14)	0.53325 (8)	0.14518 (7)	0.0127 (2)
H7A	0.567947	0.508833	0.102612	0.019*
H7B	0.509226	0.594649	0.181052	0.019*
H7C	0.358562	0.550984	0.105488	0.019*
N1	0.35774 (11)	0.35565 (6)	0.18019 (6)	0.01040 (18)
O1	0.48021 (11)	0.55760 (6)	0.35063 (5)	0.01365 (18)
H1O	0.505 (3)	0.5515 (16)	0.4166 (15)	0.043 (6)*
O2	0.36942 (11)	0.40280 (6)	0.47503 (5)	0.01410 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0094 (4)	0.0097 (4)	0.0099 (4)	0.0004 (3)	−0.0002 (3)	0.0000 (3)
C2	0.0105 (4)	0.0088 (4)	0.0099 (4)	−0.0005 (3)	−0.0007 (3)	−0.0007 (3)
C3	0.0098 (4)	0.0107 (4)	0.0098 (4)	0.0002 (3)	0.0001 (3)	−0.0001 (3)
C4	0.0142 (4)	0.0094 (4)	0.0110 (4)	−0.0005 (3)	0.0003 (3)	0.0004 (3)
C5	0.0139 (4)	0.0095 (4)	0.0121 (4)	0.0000 (3)	−0.0007 (3)	−0.0013 (3)
C6	0.0205 (5)	0.0166 (4)	0.0081 (4)	−0.0005 (4)	−0.0013 (3)	−0.0026 (3)
C7	0.0146 (4)	0.0133 (4)	0.0101 (4)	−0.0010 (3)	−0.0002 (3)	0.0028 (3)
N1	0.0120 (4)	0.0112 (4)	0.0080 (3)	0.0001 (3)	−0.0006 (3)	−0.0016 (3)
O1	0.0208 (4)	0.0104 (3)	0.0097 (3)	−0.0040 (3)	−0.0017 (3)	−0.0011 (2)
O2	0.0191 (4)	0.0151 (3)	0.0081 (3)	−0.0030 (3)	0.0000 (2)	−0.0011 (2)

Geometric parameters (Å, º)

C1—N1	1.3771 (13)	C5—H5	0.9500
C1—C2	1.3775 (14)	C6—N1	1.4700 (13)
C1—C7	1.4958 (14)	C6—H6A	0.9800
C2—O1	1.3595 (12)	C6—H6B	0.9800
C2—C3	1.4399 (14)	C6—H6C	0.9800
C3—O2	1.2709 (13)	C7—H7A	0.9800
C3—C4	1.4234 (14)	C7—H7B	0.9800
C4—C5	1.3679 (14)	C7—H7C	0.9800
C4—H4	0.9500	O1—H1O	0.93 (2)
C5—N1	1.3512 (13)
N1—C1—C2	118.96 (8)	N1—C6—H6B	109.5
N1—C1—C7	118.74 (9)	H6A—C6—H6B	109.5
C2—C1—C7	122.29 (9)	N1—C6—H6C	109.5
O1—C2—C1	118.83 (8)	H6A—C6—H6C	109.5
O1—C2—C3	118.79 (9)	H6B—C6—H6C	109.5
C1—C2—C3	122.34 (9)	C1—C7—H7A	109.5
O2—C3—C4	124.32 (9)	C1—C7—H7B	109.5
O2—C3—C2	120.68 (9)	H7A—C7—H7B	109.5
C4—C3—C2	114.98 (9)	C1—C7—H7C	109.5
C5—C4—C3	120.92 (9)	H7A—C7—H7C	109.5
C5—C4—H4	119.5	H7B—C7—H7C	109.5
C3—C4—H4	119.5	C5—N1—C1	120.85 (9)
N1—C5—C4	121.93 (9)	C5—N1—C6	119.02 (9)
N1—C5—H5	119.0	C1—N1—C6	120.13 (8)
C4—C5—H5	119.0	C2—O1—H1O	109.2 (13)
N1—C6—H6A	109.5
N1—C1—C2—O1	−179.29 (8)	C2—C3—C4—C5	−0.16 (13)
C7—C1—C2—O1	−0.38 (14)	C3—C4—C5—N1	−0.66 (15)
N1—C1—C2—C3	−1.48 (14)	C4—C5—N1—C1	0.44 (14)
C7—C1—C2—C3	177.43 (9)	C4—C5—N1—C6	179.77 (9)
O1—C2—C3—O2	0.61 (14)	C2—C1—N1—C5	0.62 (13)
C1—C2—C3—O2	−177.20 (9)	C7—C1—N1—C5	−178.33 (9)
O1—C2—C3—C4	179.04 (8)	C2—C1—N1—C6	−178.70 (9)
C1—C2—C3—C4	1.23 (13)	C7—C1—N1—C6	2.34 (13)
O2—C3—C4—C5	178.21 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.93 (2)	1.83 (2)	2.6704 (14)	149.2 (18)
C6—H6A···O2^ii	0.98	2.50	3.3878 (18)	150
C7—H7C···O2^iii	0.98	2.50	3.4601 (15)	168

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

3-Hydroxy-1,2-dimethylpyridin-4-one (Ib)

Crystal data

C7H9NO2	F(000) = 296
Mr = 139.15	Dx = 1.465 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.4847 (1) Å	Cell parameters from 5426 reflections
b = 13.6853 (3) Å	θ = 2.7–30.5°
c = 7.1462 (1) Å	µ = 0.11 mm^−1
β = 95.6583 (8)°	T = 100 K
V = 631.10 (2) Å^3	Block, colorless
Z = 4	0.33 × 0.18 × 0.16 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	1681 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 30.5°, θmin = 3.0°
Tmin = 0.705, Tmax = 0.746	h = −9→9
7716 measured reflections	k = −19→19
1922 independent reflections	l = −10→10

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 0.2705P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1922 reflections	Δρmax = 0.43 e Å^−3
97 parameters	Δρmin = −0.27 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
C1	0.39396 (15)	0.21544 (7)	0.40876 (13)	0.00929 (19)
C2	0.42242 (14)	0.31466 (7)	0.42168 (13)	0.00901 (19)
C3	0.26323 (15)	0.38332 (7)	0.35673 (13)	0.0097 (2)
C4	0.07167 (15)	0.34026 (7)	0.28596 (14)	0.0117 (2)
H4	−0.042505	0.381175	0.245672	0.014*
C5	0.04889 (15)	0.24128 (7)	0.27488 (14)	0.0113 (2)
H5	−0.080458	0.214858	0.224970	0.014*
C6	0.16938 (16)	0.07400 (7)	0.31937 (15)	0.0136 (2)
H6A	0.030437	0.061554	0.256977	0.020*
H6B	0.180813	0.045615	0.445871	0.020*
H6C	0.273046	0.044210	0.246263	0.020*
C7	0.56126 (15)	0.14404 (7)	0.47281 (14)	0.0120 (2)
H7A	0.594896	0.104351	0.365781	0.018*
H7B	0.513253	0.101437	0.569862	0.018*
H7C	0.685084	0.179601	0.524682	0.018*
N1	0.20509 (13)	0.17983 (6)	0.33287 (12)	0.00950 (18)
O1	0.60952 (11)	0.34951 (6)	0.49501 (11)	0.01269 (18)
H1O	0.608 (3)	0.4129 (15)	0.515 (3)	0.040 (5)*
O2	0.29796 (12)	0.47457 (5)	0.36221 (11)	0.01408 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0100 (4)	0.0095 (4)	0.0082 (4)	0.0001 (3)	0.0000 (3)	0.0003 (3)
C2	0.0081 (4)	0.0096 (4)	0.0091 (4)	−0.0008 (3)	−0.0008 (3)	−0.0002 (3)
C3	0.0107 (4)	0.0086 (4)	0.0094 (4)	0.0000 (3)	−0.0004 (3)	0.0007 (3)
C4	0.0095 (4)	0.0103 (4)	0.0147 (4)	0.0005 (3)	−0.0024 (3)	0.0009 (3)
C5	0.0095 (4)	0.0109 (5)	0.0130 (4)	−0.0011 (3)	−0.0011 (3)	0.0010 (3)
C6	0.0160 (5)	0.0061 (4)	0.0183 (5)	−0.0027 (3)	−0.0010 (4)	−0.0007 (4)
C7	0.0121 (4)	0.0095 (4)	0.0138 (4)	0.0028 (3)	−0.0016 (3)	−0.0001 (3)
N1	0.0113 (4)	0.0069 (4)	0.0100 (4)	−0.0014 (3)	−0.0002 (3)	0.0002 (3)
O1	0.0091 (3)	0.0087 (3)	0.0191 (4)	−0.0011 (3)	−0.0041 (3)	−0.0019 (3)
O2	0.0151 (3)	0.0067 (3)	0.0193 (4)	−0.0012 (3)	−0.0038 (3)	0.0003 (3)

Geometric parameters (Å, º)

C1—C2	1.3722 (13)	C5—H5	0.9500
C1—N1	1.3786 (12)	C6—N1	1.4684 (12)
C1—C7	1.4978 (13)	C6—H6A	0.9800
C2—O1	1.3597 (11)	C6—H6B	0.9800
C2—C3	1.4386 (13)	C6—H6C	0.9800
C3—O2	1.2689 (12)	C7—H7A	0.9800
C3—C4	1.4220 (13)	C7—H7B	0.9800
C4—C5	1.3642 (14)	C7—H7C	0.9800
C4—H4	0.9500	O1—H1O	0.88 (2)
C5—N1	1.3498 (13)
C2—C1—N1	118.99 (9)	N1—C6—H6B	109.5
C2—C1—C7	122.44 (9)	H6A—C6—H6B	109.5
N1—C1—C7	118.57 (9)	N1—C6—H6C	109.5
O1—C2—C1	118.82 (9)	H6A—C6—H6C	109.5
O1—C2—C3	118.68 (9)	H6B—C6—H6C	109.5
C1—C2—C3	122.49 (9)	C1—C7—H7A	109.5
O2—C3—C4	124.40 (9)	C1—C7—H7B	109.5
O2—C3—C2	120.89 (9)	H7A—C7—H7B	109.5
C4—C3—C2	114.70 (9)	C1—C7—H7C	109.5
C5—C4—C3	121.19 (9)	H7A—C7—H7C	109.5
C5—C4—H4	119.4	H7B—C7—H7C	109.5
C3—C4—H4	119.4	C5—N1—C1	120.75 (8)
N1—C5—C4	121.81 (9)	C5—N1—C6	119.05 (8)
N1—C5—H5	119.1	C1—N1—C6	120.18 (8)
C4—C5—H5	119.1	C2—O1—H1O	112.5 (12)
N1—C6—H6A	109.5
N1—C1—C2—O1	−179.40 (8)	C2—C3—C4—C5	−2.73 (14)
C7—C1—C2—O1	0.13 (14)	C3—C4—C5—N1	1.04 (16)
N1—C1—C2—C3	−0.81 (14)	C4—C5—N1—C1	1.02 (14)
C7—C1—C2—C3	178.71 (9)	C4—C5—N1—C6	179.19 (9)
O1—C2—C3—O2	2.11 (14)	C2—C1—N1—C5	−1.11 (13)
C1—C2—C3—O2	−176.48 (9)	C7—C1—N1—C5	179.34 (9)
O1—C2—C3—C4	−178.77 (8)	C2—C1—N1—C6	−179.26 (9)
C1—C2—C3—C4	2.65 (13)	C7—C1—N1—C6	1.20 (13)
O2—C3—C4—C5	176.36 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.88 (2)	1.85 (2)	2.6602 (10)	153.0 (17)
C6—H6A···O2^ii	0.98	2.51	3.4560 (13)	161
C7—H7A···O2^iii	0.98	2.55	3.5177 (13)	168

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

3-Hydroxy-1,2-dimethylpyridin-4-one (Ic)

Crystal data

C7H9NO2	F(000) = 888
Mr = 139.15	Dx = 1.452 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.4132 (8) Å	Cell parameters from 9985 reflections
b = 13.7057 (7) Å	θ = 3.0–30.6°
c = 7.1809 (7) Å	µ = 0.11 mm^−1
β = 91.775 (1)°	T = 100 K
V = 1909.7 (2) Å^3	Needle, colorless
Z = 12	0.26 × 0.13 × 0.11 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	4477 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.033
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 30.6°, θmin = 2.6°
Tmin = 0.679, Tmax = 0.746	h = −27→27
24981 measured reflections	k = −19→15
5838 independent reflections	l = −10→9

Refinement

Refinement on F^2	1370 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 1.601P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5838 reflections	Δρmax = 0.42 e Å^−3
467 parameters	Δρmin = −0.29 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.46611 (6)	−0.28431 (9)	0.57997 (17)	0.0081 (2)
C2A	0.47566 (6)	−0.18486 (9)	0.57352 (18)	0.0083 (2)
C3A	0.42321 (7)	−0.11656 (9)	0.62421 (18)	0.0088 (2)
C4A	0.35989 (7)	−0.15983 (10)	0.67782 (18)	0.0103 (2)
H4A	0.322757	−0.119246	0.712583	0.012*
C5A	0.35208 (7)	−0.25888 (10)	0.67973 (19)	0.0104 (2)
H5A	0.309225	−0.285577	0.714803	0.012*
C6A	0.39108 (7)	−0.42600 (10)	0.6381 (2)	0.0132 (3)
H6A	0.400569	−0.454201	0.516086	0.020*
H6B	0.342955	−0.438462	0.667873	0.020*
H6C	0.421544	−0.455852	0.733352	0.020*
C7A	0.52179 (7)	−0.35513 (10)	0.53413 (19)	0.0111 (2)
H7A	0.505416	−0.398200	0.433206	0.017*
H7B	0.533888	−0.394246	0.644612	0.017*
H7C	0.562504	−0.319318	0.494576	0.017*
N1A	0.40336 (6)	−0.32014 (8)	0.63331 (15)	0.0092 (2)
O1A	0.53803 (5)	−0.14956 (7)	0.52226 (14)	0.0121 (2)
O2A	0.43479 (5)	−0.02526 (7)	0.62380 (14)	0.0129 (2)
H1O	0.5349 (12)	−0.0861 (17)	0.496 (3)	0.035 (6)*
C1B	0.20010 (7)	0.21488 (10)	0.55646 (18)	0.0086 (2)	0.9456 (14)
C2B	0.19086 (7)	0.31423 (10)	0.54672 (18)	0.0085 (2)	0.9456 (14)
C3B	0.24321 (7)	0.38244 (10)	0.60838 (19)	0.0087 (2)	0.9456 (14)
C4B	0.30614 (8)	0.33919 (12)	0.6745 (2)	0.0104 (4)	0.9456 (14)
H4B	0.343028	0.379766	0.717195	0.013*	0.9456 (14)
C5B	0.31408 (9)	0.24015 (13)	0.6772 (3)	0.0107 (5)	0.9456 (14)
H5B	0.356890	0.213449	0.719818	0.013*	0.9456 (14)
C6B	0.27513 (8)	0.07285 (10)	0.6269 (2)	0.0138 (3)	0.9456 (14)
H6D	0.323089	0.060234	0.666315	0.021*	0.9456 (14)
H6E	0.266237	0.045090	0.502713	0.021*	0.9456 (14)
H6F	0.244218	0.042676	0.715590	0.021*	0.9456 (14)
C7B	0.14437 (7)	0.14403 (10)	0.5019 (2)	0.0115 (3)	0.9456 (14)
H7D	0.102485	0.179857	0.464658	0.017*	0.9456 (14)
H7E	0.134817	0.101691	0.607993	0.017*	0.9456 (14)
H7F	0.159333	0.104167	0.397312	0.017*	0.9456 (14)
N1B	0.26288 (6)	0.17893 (9)	0.62105 (17)	0.0095 (2)	0.9456 (14)
O1B	0.12887 (5)	0.34919 (8)	0.48237 (15)	0.0121 (2)	0.9456 (14)
H2O	0.131602	0.409816	0.467123	0.018*	0.9456 (14)
O2B	0.23156 (5)	0.47390 (7)	0.60577 (15)	0.0127 (2)	0.9456 (14)
C1B'	0.2020 (9)	0.2174 (11)	0.803 (3)	0.0099 (15)	0.0544 (14)
C2B'	0.1915 (8)	0.3184 (11)	0.808 (3)	0.0106 (15)	0.0544 (14)
C3B'	0.2465 (9)	0.3835 (11)	0.776 (3)	0.0087 (17)	0.0544 (14)
C4B'	0.3099 (11)	0.3438 (14)	0.721 (5)	0.0089 (18)	0.0544 (14)
H4B'	0.346864	0.385747	0.690289	0.011*	0.0544 (14)
C5B'	0.3179 (15)	0.2420 (16)	0.710 (8)	0.0092 (18)	0.0544 (14)
H5B'	0.359730	0.214846	0.668235	0.011*	0.0544 (14)
C6B'	0.2787 (12)	0.0730 (15)	0.749 (4)	0.009 (2)	0.0544 (14)
H6D'	0.262181	0.041262	0.861222	0.014*	0.0544 (14)
H6E'	0.328290	0.061280	0.739101	0.014*	0.0544 (14)
H6F'	0.254291	0.046010	0.638909	0.014*	0.0544 (14)
C7B'	0.1491 (12)	0.1490 (18)	0.850 (4)	0.012 (2)	0.0544 (14)
H7D'	0.125993	0.124732	0.736147	0.019*	0.0544 (14)
H7E'	0.115336	0.181491	0.927872	0.019*	0.0544 (14)
H7F'	0.169856	0.094149	0.919294	0.019*	0.0544 (14)
N1B'	0.2653 (8)	0.1827 (11)	0.760 (3)	0.0083 (16)	0.0544 (14)
O1B'	0.1301 (9)	0.3504 (14)	0.869 (3)	0.014 (2)	0.0544 (14)
H2O'	0.132746	0.410381	0.892397	0.021*	0.0544 (14)
O2B'	0.2346 (8)	0.4742 (12)	0.774 (2)	0.0079 (19)	0.0544 (14)
C1C	0.13170 (7)	0.78333 (10)	0.38435 (19)	0.0093 (2)	0.9579 (13)
C2C	0.14153 (7)	0.68376 (10)	0.39421 (19)	0.0090 (2)	0.9579 (13)
C3C	0.08816 (7)	0.61553 (10)	0.33973 (19)	0.0092 (2)	0.9579 (13)
C4C	0.02445 (7)	0.65834 (10)	0.2810 (2)	0.0115 (3)	0.9579 (13)
H4C	−0.013496	0.617418	0.247973	0.014*	0.9579 (13)
C5C	0.01680 (7)	0.75751 (10)	0.2710 (2)	0.0110 (3)	0.9579 (13)
H5C	−0.026133	0.783893	0.228564	0.013*	0.9579 (13)
C6C	0.05691 (8)	0.92464 (10)	0.3083 (2)	0.0134 (3)	0.9579 (13)
H6G	0.092073	0.954450	0.231512	0.020*	0.9579 (13)
H6H	0.059634	0.952901	0.433672	0.020*	0.9579 (13)
H6I	0.011137	0.937086	0.251898	0.020*	0.9579 (13)
C7C	0.18718 (8)	0.85467 (12)	0.4391 (2)	0.0117 (3)	0.9579 (13)
H7G	0.199515	0.893173	0.330051	0.018*	0.9579 (13)
H7H	0.227835	0.819242	0.487017	0.018*	0.9579 (13)
H7I	0.170478	0.898276	0.535983	0.018*	0.9579 (13)
N1C	0.06873 (6)	0.81879 (8)	0.32005 (16)	0.0092 (2)	0.9579 (13)
O1C	0.20417 (6)	0.64901 (9)	0.45377 (17)	0.0128 (2)	0.9579 (13)
H3O	0.201115	0.588978	0.475550	0.019*	0.9579 (13)
O2C	0.09956 (5)	0.52419 (7)	0.34355 (15)	0.0139 (2)	0.9579 (13)
C1C'	0.1324 (12)	0.7169 (15)	0.448 (5)	0.0093 (15)	0.0421 (13)
C2C'	0.1439 (10)	0.8177 (15)	0.447 (5)	0.0094 (17)	0.0421 (13)
C3C'	0.0904 (11)	0.8805 (13)	0.506 (4)	0.0100 (17)	0.0421 (13)
C4C'	0.0281 (11)	0.8388 (13)	0.563 (4)	0.0118 (19)	0.0421 (13)
H4C'	−0.007943	0.879755	0.604006	0.014*	0.0421 (13)
C5C'	0.0190 (11)	0.7370 (14)	0.562 (4)	0.0112 (18)	0.0421 (13)
H5C'	−0.023742	0.708783	0.593675	0.013*	0.0421 (13)
C6C'	0.0602 (16)	0.5701 (18)	0.525 (4)	0.011 (2)	0.0421 (13)
H6G'	0.040155	0.554665	0.645254	0.017*	0.0421 (13)
H6H'	0.104031	0.535264	0.514573	0.017*	0.0421 (13)
H6I'	0.028398	0.549913	0.423873	0.017*	0.0421 (13)
C7C'	0.1858 (19)	0.647 (3)	0.419 (6)	0.011 (2)	0.0421 (13)
H7G'	0.168763	0.596626	0.332446	0.016*	0.0421 (13)
H7H'	0.199690	0.617262	0.537844	0.016*	0.0421 (13)
H7I'	0.225525	0.680028	0.365532	0.016*	0.0421 (13)
N1C'	0.0729 (10)	0.6798 (12)	0.513 (4)	0.0102 (15)	0.0421 (13)
O1C'	0.2068 (15)	0.850 (2)	0.397 (4)	0.010 (2)	0.0421 (13)
H3O'	0.232241	0.802362	0.374784	0.015*	0.0421 (13)
O2C'	0.1006 (12)	0.9709 (17)	0.504 (3)	0.011 (2)	0.0421 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0091 (5)	0.0081 (5)	0.0071 (5)	0.0000 (4)	0.0000 (4)	0.0007 (4)
C2A	0.0080 (5)	0.0085 (5)	0.0085 (6)	−0.0008 (4)	0.0004 (4)	0.0008 (4)
C3A	0.0097 (5)	0.0086 (6)	0.0082 (6)	0.0000 (4)	−0.0001 (4)	0.0001 (4)
C4A	0.0087 (5)	0.0098 (6)	0.0125 (6)	0.0009 (4)	0.0012 (4)	0.0001 (4)
C5A	0.0088 (6)	0.0101 (6)	0.0123 (6)	−0.0011 (4)	0.0005 (4)	0.0007 (4)
C6A	0.0155 (6)	0.0064 (5)	0.0178 (7)	−0.0031 (5)	0.0011 (5)	0.0013 (5)
C7A	0.0123 (6)	0.0080 (6)	0.0130 (6)	0.0023 (5)	0.0012 (4)	0.0006 (5)
N1A	0.0107 (5)	0.0063 (5)	0.0107 (5)	−0.0015 (4)	0.0000 (4)	0.0005 (4)
O1A	0.0094 (4)	0.0083 (4)	0.0189 (5)	−0.0013 (4)	0.0042 (3)	0.0023 (4)
O2A	0.0142 (5)	0.0066 (4)	0.0181 (5)	−0.0006 (3)	0.0035 (4)	−0.0004 (3)
C1B	0.0094 (6)	0.0081 (6)	0.0084 (6)	−0.0005 (5)	0.0008 (4)	0.0002 (4)
C2B	0.0078 (5)	0.0089 (6)	0.0088 (6)	0.0006 (5)	0.0003 (4)	0.0004 (4)
C3B	0.0098 (6)	0.0077 (6)	0.0086 (6)	−0.0001 (5)	0.0011 (4)	0.0000 (4)
C4B	0.0092 (6)	0.0099 (6)	0.0122 (9)	−0.0009 (5)	0.0000 (5)	−0.0006 (5)
C5B	0.0087 (6)	0.0106 (6)	0.0127 (11)	0.0010 (5)	0.0000 (6)	0.0015 (5)
C6B	0.0150 (7)	0.0063 (6)	0.0202 (8)	0.0028 (5)	−0.0007 (5)	0.0020 (5)
C7B	0.0125 (6)	0.0092 (6)	0.0127 (6)	−0.0029 (5)	0.0002 (5)	−0.0003 (5)
N1B	0.0104 (5)	0.0070 (5)	0.0112 (5)	0.0019 (4)	0.0002 (4)	0.0007 (4)
O1B	0.0095 (5)	0.0075 (5)	0.0191 (5)	0.0003 (4)	−0.0043 (4)	0.0013 (4)
O2B	0.0134 (5)	0.0063 (5)	0.0181 (5)	0.0007 (4)	−0.0021 (4)	0.0004 (4)
C1B'	0.009 (3)	0.008 (3)	0.012 (3)	0.000 (3)	0.000 (3)	0.001 (3)
C2B'	0.010 (3)	0.009 (3)	0.014 (3)	0.002 (3)	0.000 (3)	−0.001 (3)
C3B'	0.009 (3)	0.007 (3)	0.010 (3)	0.000 (3)	−0.001 (3)	0.001 (3)
C4B'	0.008 (3)	0.007 (3)	0.012 (3)	0.003 (3)	−0.001 (3)	0.001 (3)
C5B'	0.008 (3)	0.007 (3)	0.012 (3)	−0.001 (3)	0.000 (3)	0.001 (3)
C6B'	0.010 (4)	0.007 (4)	0.012 (4)	0.002 (4)	0.000 (4)	0.003 (4)
C7B'	0.012 (4)	0.011 (4)	0.014 (4)	−0.003 (4)	0.002 (4)	0.001 (4)
N1B'	0.007 (3)	0.006 (3)	0.011 (3)	0.001 (3)	0.000 (3)	0.001 (3)
O1B'	0.012 (4)	0.014 (4)	0.016 (4)	0.001 (4)	0.001 (3)	0.000 (4)
O2B'	0.008 (4)	0.005 (4)	0.011 (4)	0.003 (3)	0.000 (3)	−0.001 (3)
C1C	0.0097 (6)	0.0084 (6)	0.0097 (6)	−0.0003 (5)	0.0003 (4)	0.0002 (5)
C2C	0.0090 (6)	0.0079 (6)	0.0100 (6)	0.0011 (5)	−0.0004 (4)	0.0003 (5)
C3C	0.0109 (6)	0.0076 (6)	0.0091 (6)	0.0006 (5)	−0.0004 (4)	−0.0011 (4)
C4C	0.0102 (6)	0.0092 (6)	0.0149 (6)	−0.0002 (5)	−0.0024 (5)	−0.0012 (5)
C5C	0.0096 (6)	0.0109 (6)	0.0125 (6)	0.0014 (5)	−0.0016 (5)	−0.0002 (5)
C6C	0.0153 (6)	0.0061 (6)	0.0187 (7)	0.0017 (5)	−0.0010 (5)	0.0007 (5)
C7C	0.0117 (7)	0.0094 (6)	0.0140 (7)	−0.0033 (6)	−0.0009 (5)	0.0007 (5)
N1C	0.0107 (5)	0.0056 (5)	0.0113 (5)	0.0017 (4)	−0.0005 (4)	0.0002 (4)
O1C	0.0102 (5)	0.0085 (5)	0.0194 (6)	0.0017 (4)	−0.0043 (4)	0.0022 (4)
O2C	0.0154 (5)	0.0065 (5)	0.0194 (5)	0.0013 (4)	−0.0048 (4)	−0.0003 (4)
C1C'	0.009 (3)	0.007 (3)	0.012 (3)	0.000 (3)	−0.002 (3)	−0.002 (3)
C2C'	0.010 (3)	0.007 (3)	0.012 (3)	−0.001 (3)	−0.003 (3)	0.000 (3)
C3C'	0.011 (3)	0.008 (3)	0.011 (3)	0.000 (3)	−0.002 (3)	0.001 (3)
C4C'	0.013 (3)	0.010 (3)	0.013 (3)	0.000 (3)	−0.002 (3)	0.001 (3)
C5C'	0.012 (3)	0.009 (3)	0.012 (3)	0.000 (3)	−0.001 (3)	0.000 (3)
C6C'	0.012 (4)	0.010 (4)	0.012 (4)	−0.001 (4)	−0.001 (4)	0.000 (4)
C7C'	0.011 (4)	0.008 (3)	0.012 (4)	−0.002 (3)	−0.002 (3)	0.002 (3)
N1C'	0.011 (3)	0.008 (3)	0.011 (3)	0.000 (3)	−0.002 (3)	0.000 (3)
O1C'	0.010 (3)	0.007 (3)	0.012 (3)	−0.001 (3)	−0.001 (3)	−0.001 (3)
O2C'	0.012 (4)	0.009 (4)	0.013 (4)	0.000 (3)	0.001 (3)	0.001 (3)

Geometric parameters (Å, º)

C1A—C2A	1.3767 (17)	C5B'—H5B'	0.9500
C1A—N1A	1.3786 (16)	C6B'—N1B'	1.53 (2)
C1A—C7A	1.4969 (18)	C6B'—H6D'	0.9800
C2A—O1A	1.3649 (15)	C6B'—H6E'	0.9800
C2A—C3A	1.4383 (18)	C6B'—H6F'	0.9800
C3A—O2A	1.2713 (16)	C7B'—H7D'	0.9800
C3A—C4A	1.4285 (18)	C7B'—H7E'	0.9800
C4A—C5A	1.3660 (18)	C7B'—H7F'	0.9800
C4A—H4A	0.9500	O1B'—H2O'	0.8400
C5A—N1A	1.3519 (17)	C1C—C2C	1.3794 (19)
C5A—H5A	0.9500	C1C—N1C	1.3816 (17)
C6A—N1A	1.4708 (17)	C1C—C7C	1.498 (2)
C6A—H6A	0.9800	C2C—O1C	1.3625 (17)
C6A—H6B	0.9800	C2C—C3C	1.4409 (19)
C6A—H6C	0.9800	C3C—O2C	1.2715 (16)
C7A—H7A	0.9800	C3C—C4C	1.4212 (18)
C7A—H7B	0.9800	C4C—C5C	1.3689 (19)
C7A—H7C	0.9800	C4C—H4C	0.9500
O1A—H1O	0.89 (2)	C5C—N1C	1.3505 (18)
C1B—C2B	1.3750 (19)	C5C—H5C	0.9500
C1B—N1B	1.3814 (17)	C6C—N1C	1.4708 (18)
C1B—C7B	1.4968 (19)	C6C—H6G	0.9800
C2B—O1B	1.3627 (16)	C6C—H6H	0.9800
C2B—C3B	1.4405 (18)	C6C—H6I	0.9800
C3B—O2B	1.2738 (16)	C7C—H7G	0.9800
C3B—C4B	1.426 (2)	C7C—H7H	0.9800
C4B—C5B	1.366 (2)	C7C—H7I	0.9800
C4B—H4B	0.9500	O1C—H3O	0.8400
C5B—N1B	1.353 (2)	C1C'—N1C'	1.358 (16)
C5B—H5B	0.9500	C1C'—C2C'	1.400 (14)
C6B—N1B	1.4736 (18)	C1C'—C7C'	1.43 (3)
C6B—H6D	0.9800	C2C'—O1C'	1.36 (3)
C6B—H6E	0.9800	C2C'—C3C'	1.423 (13)
C6B—H6F	0.9800	C3C'—O2C'	1.25 (3)
C7B—H7D	0.9800	C3C'—C4C'	1.412 (13)
C7B—H7E	0.9800	C4C'—C5C'	1.406 (14)
C7B—H7F	0.9800	C4C'—H4C'	0.9500
O1B—H2O	0.8400	C5C'—N1C'	1.362 (16)
C1B'—N1B'	1.362 (15)	C5C'—H5C'	0.9500
C1B'—C2B'	1.400 (13)	C6C'—N1C'	1.53 (2)
C1B'—C7B'	1.44 (3)	C6C'—H6G'	0.9800
C2B'—O1B'	1.36 (2)	C6C'—H6H'	0.9800
C2B'—C3B'	1.415 (13)	C6C'—H6I'	0.9800
C3B'—O2B'	1.26 (2)	C7C'—H7G'	0.9800
C3B'—C4B'	1.416 (13)	C7C'—H7H'	0.9800
C4B'—C5B'	1.406 (14)	C7C'—H7I'	0.9800
C4B'—H4B'	0.9500	O1C'—H3O'	0.8400
C5B'—N1B'	1.361 (17)
C2A—C1A—N1A	118.89 (11)	N1B'—C6B'—H6E'	109.5
C2A—C1A—C7A	122.39 (11)	H6D'—C6B'—H6E'	109.5
N1A—C1A—C7A	118.71 (11)	N1B'—C6B'—H6F'	109.5
O1A—C2A—C1A	118.79 (11)	H6D'—C6B'—H6F'	109.5
O1A—C2A—C3A	118.59 (11)	H6E'—C6B'—H6F'	109.5
C1A—C2A—C3A	122.60 (12)	C1B'—C7B'—H7D'	109.5
O2A—C3A—C4A	124.27 (12)	C1B'—C7B'—H7E'	109.5
O2A—C3A—C2A	120.88 (12)	H7D'—C7B'—H7E'	109.5
C4A—C3A—C2A	114.83 (11)	C1B'—C7B'—H7F'	109.5
C5A—C4A—C3A	120.80 (12)	H7D'—C7B'—H7F'	109.5
C5A—C4A—H4A	119.6	H7E'—C7B'—H7F'	109.5
C3A—C4A—H4A	119.6	C5B'—N1B'—C1B'	122.7 (15)
N1A—C5A—C4A	122.14 (12)	C5B'—N1B'—C6B'	116.4 (16)
N1A—C5A—H5A	118.9	C1B'—N1B'—C6B'	120.7 (16)
C4A—C5A—H5A	118.9	C2B'—O1B'—H2O'	109.5
N1A—C6A—H6A	109.5	C2C—C1C—N1C	119.00 (13)
N1A—C6A—H6B	109.5	C2C—C1C—C7C	122.35 (13)
H6A—C6A—H6B	109.5	N1C—C1C—C7C	118.65 (13)
N1A—C6A—H6C	109.5	O1C—C2C—C1C	118.86 (12)
H6A—C6A—H6C	109.5	O1C—C2C—C3C	119.06 (13)
H6B—C6A—H6C	109.5	C1C—C2C—C3C	122.07 (13)
C1A—C7A—H7A	109.5	O2C—C3C—C4C	124.21 (12)
C1A—C7A—H7B	109.5	O2C—C3C—C2C	120.66 (12)
H7A—C7A—H7B	109.5	C4C—C3C—C2C	115.12 (12)
C1A—C7A—H7C	109.5	C5C—C4C—C3C	121.16 (13)
H7A—C7A—H7C	109.5	C5C—C4C—H4C	119.4
H7B—C7A—H7C	109.5	C3C—C4C—H4C	119.4
C5A—N1A—C1A	120.73 (11)	N1C—C5C—C4C	121.67 (13)
C5A—N1A—C6A	119.07 (11)	N1C—C5C—H5C	119.2
C1A—N1A—C6A	120.20 (11)	C4C—C5C—H5C	119.2
C2A—O1A—H1O	110.3 (15)	N1C—C6C—H6G	109.5
C2B—C1B—N1B	118.86 (12)	N1C—C6C—H6H	109.5
C2B—C1B—C7B	122.48 (12)	H6G—C6C—H6H	109.5
N1B—C1B—C7B	118.65 (12)	N1C—C6C—H6I	109.5
O1B—C2B—C1B	118.55 (12)	H6G—C6C—H6I	109.5
O1B—C2B—C3B	118.90 (12)	H6H—C6C—H6I	109.5
C1B—C2B—C3B	122.51 (12)	C1C—C7C—H7G	109.5
O2B—C3B—C4B	124.33 (13)	C1C—C7C—H7H	109.5
O2B—C3B—C2B	120.72 (12)	H7G—C7C—H7H	109.5
C4B—C3B—C2B	114.93 (12)	C1C—C7C—H7I	109.5
C5B—C4B—C3B	120.86 (14)	H7G—C7C—H7I	109.5
C5B—C4B—H4B	119.6	H7H—C7C—H7I	109.5
C3B—C4B—H4B	119.6	C5C—N1C—C1C	120.93 (12)
N1B—C5B—C4B	122.04 (15)	C5C—N1C—C6C	118.98 (12)
N1B—C5B—H5B	119.0	C1C—N1C—C6C	120.07 (12)
C4B—C5B—H5B	119.0	C2C—O1C—H3O	109.5
N1B—C6B—H6D	109.5	N1C'—C1C'—C2C'	120.5 (14)
N1B—C6B—H6E	109.5	N1C'—C1C'—C7C'	115 (2)
H6D—C6B—H6E	109.5	C2C'—C1C'—C7C'	123 (2)
N1B—C6B—H6F	109.5	O1C'—C2C'—C1C'	118 (2)
H6D—C6B—H6F	109.5	O1C'—C2C'—C3C'	123 (2)
H6E—C6B—H6F	109.5	C1C'—C2C'—C3C'	118.6 (10)
C1B—C7B—H7D	109.5	O2C'—C3C'—C4C'	122.6 (19)
C1B—C7B—H7E	109.5	O2C'—C3C'—C2C'	118.6 (19)
H7D—C7B—H7E	109.5	C4C'—C3C'—C2C'	118.8 (11)
C1B—C7B—H7F	109.5	C5C'—C4C'—C3C'	120.5 (11)
H7D—C7B—H7F	109.5	C5C'—C4C'—H4C'	119.7
H7E—C7B—H7F	109.5	C3C'—C4C'—H4C'	119.7
C5B—N1B—C1B	120.75 (13)	N1C'—C5C'—C4C'	118.4 (14)
C5B—N1B—C6B	119.15 (13)	N1C'—C5C'—H5C'	120.8
C1B—N1B—C6B	120.09 (12)	C4C'—C5C'—H5C'	120.8
C2B—O1B—H2O	109.5	N1C'—C6C'—H6G'	109.5
N1B'—C1B'—C2B'	119.0 (12)	N1C'—C6C'—H6H'	109.5
N1B'—C1B'—C7B'	118.9 (16)	H6G'—C6C'—H6H'	109.5
C2B'—C1B'—C7B'	122.1 (17)	N1C'—C6C'—H6I'	109.5
O1B'—C2B'—C1B'	117.4 (15)	H6G'—C6C'—H6I'	109.5
O1B'—C2B'—C3B'	121.5 (15)	H6H'—C6C'—H6I'	109.5
C1B'—C2B'—C3B'	120.6 (10)	C1C'—C7C'—H7G'	109.5
O2B'—C3B'—C2B'	119.0 (16)	C1C'—C7C'—H7H'	109.5
O2B'—C3B'—C4B'	122.2 (16)	H7G'—C7C'—H7H'	109.5
C2B'—C3B'—C4B'	118.0 (10)	C1C'—C7C'—H7I'	109.5
C5B'—C4B'—C3B'	119.7 (11)	H7G'—C7C'—H7I'	109.5
C5B'—C4B'—H4B'	120.2	H7H'—C7C'—H7I'	109.5
C3B'—C4B'—H4B'	120.2	C1C'—N1C'—C5C'	122.8 (15)
N1B'—C5B'—C4B'	119.5 (14)	C1C'—N1C'—C6C'	121.9 (19)
N1B'—C5B'—H5B'	120.2	C5C'—N1C'—C6C'	115.1 (19)
C4B'—C5B'—H5B'	120.2	C2C'—O1C'—H3O'	109.5
N1B'—C6B'—H6D'	109.5
N1A—C1A—C2A—O1A	179.43 (11)	C2B'—C3B'—C4B'—C5B'	−4 (5)
C7A—C1A—C2A—O1A	0.44 (18)	C3B'—C4B'—C5B'—N1B'	−2 (7)
N1A—C1A—C2A—C3A	1.40 (19)	C4B'—C5B'—N1B'—C1B'	7 (6)
C7A—C1A—C2A—C3A	−177.59 (12)	C4B'—C5B'—N1B'—C6B'	−179 (4)
O1A—C2A—C3A—O2A	−0.91 (18)	C2B'—C1B'—N1B'—C5B'	−4 (4)
C1A—C2A—C3A—O2A	177.13 (12)	C7B'—C1B'—N1B'—C5B'	179 (3)
O1A—C2A—C3A—C4A	−179.35 (11)	C2B'—C1B'—N1B'—C6B'	−179 (2)
C1A—C2A—C3A—C4A	−1.32 (18)	C7B'—C1B'—N1B'—C6B'	4 (3)
O2A—C3A—C4A—C5A	−178.08 (13)	N1C—C1C—C2C—O1C	178.56 (12)
C2A—C3A—C4A—C5A	0.31 (18)	C7C—C1C—C2C—O1C	−0.8 (2)
C3A—C4A—C5A—N1A	0.6 (2)	N1C—C1C—C2C—C3C	−0.1 (2)
C4A—C5A—N1A—C1A	−0.6 (2)	C7C—C1C—C2C—C3C	−179.41 (13)
C4A—C5A—N1A—C6A	−179.81 (12)	O1C—C2C—C3C—O2C	−1.3 (2)
C2A—C1A—N1A—C5A	−0.41 (18)	C1C—C2C—C3C—O2C	177.28 (13)
C7A—C1A—N1A—C5A	178.61 (12)	O1C—C2C—C3C—C4C	179.54 (13)
C2A—C1A—N1A—C6A	178.80 (12)	C1C—C2C—C3C—C4C	−1.8 (2)
C7A—C1A—N1A—C6A	−2.19 (17)	O2C—C3C—C4C—C5C	−176.53 (14)
N1B—C1B—C2B—O1B	179.82 (12)	C2C—C3C—C4C—C5C	2.5 (2)
C7B—C1B—C2B—O1B	−1.0 (2)	C3C—C4C—C5C—N1C	−1.4 (2)
N1B—C1B—C2B—C3B	−2.6 (2)	C4C—C5C—N1C—C1C	−0.7 (2)
C7B—C1B—C2B—C3B	176.65 (13)	C4C—C5C—N1C—C6C	−179.27 (13)
O1B—C2B—C3B—O2B	1.1 (2)	C2C—C1C—N1C—C5C	1.4 (2)
C1B—C2B—C3B—O2B	−176.50 (13)	C7C—C1C—N1C—C5C	−179.22 (13)
O1B—C2B—C3B—C4B	179.60 (12)	C2C—C1C—N1C—C6C	179.96 (13)
C1B—C2B—C3B—C4B	1.99 (19)	C7C—C1C—N1C—C6C	−0.67 (19)
O2B—C3B—C4B—C5B	178.31 (15)	N1C'—C1C'—C2C'—O1C'	174 (3)
C2B—C3B—C4B—C5B	−0.1 (2)	C7C'—C1C'—C2C'—O1C'	7 (5)
C3B—C4B—C5B—N1B	−1.2 (3)	N1C'—C1C'—C2C'—C3C'	−4 (5)
C4B—C5B—N1B—C1B	0.6 (2)	C7C'—C1C'—C2C'—C3C'	−170 (3)
C4B—C5B—N1B—C6B	179.73 (15)	O1C'—C2C'—C3C'—O2C'	3 (5)
C2B—C1B—N1B—C5B	1.2 (2)	C1C'—C2C'—C3C'—O2C'	−180 (3)
C7B—C1B—N1B—C5B	−178.03 (14)	O1C'—C2C'—C3C'—C4C'	−177 (3)
C2B—C1B—N1B—C6B	−177.87 (13)	C1C'—C2C'—C3C'—C4C'	1 (5)
C7B—C1B—N1B—C6B	2.88 (19)	O2C'—C3C'—C4C'—C5C'	180 (3)
N1B'—C1B'—C2B'—O1B'	−174 (2)	C2C'—C3C'—C4C'—C5C'	−1 (5)
C7B'—C1B'—C2B'—O1B'	3 (4)	C3C'—C4C'—C5C'—N1C'	4 (5)
N1B'—C1B'—C2B'—C3B'	−2 (4)	C2C'—C1C'—N1C'—C5C'	7 (5)
C7B'—C1B'—C2B'—C3B'	174 (2)	C7C'—C1C'—N1C'—C5C'	175 (3)
O1B'—C2B'—C3B'—O2B'	−12 (4)	C2C'—C1C'—N1C'—C6C'	−177 (3)
C1B'—C2B'—C3B'—O2B'	177 (2)	C7C'—C1C'—N1C'—C6C'	−9 (5)
O1B'—C2B'—C3B'—C4B'	177 (3)	C4C'—C5C'—N1C'—C1C'	−7 (5)
C1B'—C2B'—C3B'—C4B'	6 (4)	C4C'—C5C'—N1C'—C6C'	177 (3)
O2B'—C3B'—C4B'—C5B'	−174 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O···O2A^i	0.89 (2)	1.86 (2)	2.6747 (14)	151 (2)
C6A—H6B···O2B^ii	0.98	2.50	3.3886 (17)	150
C7A—H7B···O2A^iii	0.98	2.51	3.4718 (17)	167
O1B—H2O···O2C	0.84	1.90	2.6524 (15)	149
C6B—H6D···O2A	0.98	2.49	3.3793 (18)	150
C7B—H7E···O2C^iv	0.98	2.53	3.4962 (18)	171
O1C—H3O···O2B	0.84	1.92	2.6829 (16)	151
C6C—H6I···O2C^v	0.98	2.53	3.4745 (18)	161
C7C—H7G···O2B^vi	0.98	2.52	3.4814 (19)	166

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