Strategic synthon approach in obtaining cocrystals and cocrystal polymorphs of a high-Z′ system deferiprone – an anti-thalassemia drug

Compounds with more than one molecule in the crystallographic asymmetric unit (Z′ > 1) display a noticeably stronger propensity to form cocrystals. Deferiprone is an anti-thalassemia drug known to exhibit polymorphic behaviour. Previously, three polymorphs were reported out of which one of them exhibited Z′ > 1. In the present manuscript, a fourth polymorph of deferiprone was identified and it also possessed Z′ > 1. All the four polymorphs showed similar hydrogen bonding features and differed in crystal packing. The ability of deferiprone to crystallize as Z′ > 1 prompted us to investigate the hydrogen bonding and synthon variation upon cocrystallization of deferiprone with hydroxyl-group-containing coformers such as catechol, hydro­quinone, phloroglucinol, resorcinol and pyrogallol. Crystallization attempts along with PXRD analysis aided in obtaining 11 new cocrystal structures which involve different stoichiometric cocrystals and some polymorphs. Synthon analysis, crystal packing as well as thermal behaviour were assessed and compared. The presence of multiple phases in each cocrystal system in its respective bulk powders was identified and quantified using PXRD and Rietveld analysis. Homosynthons were observed in three co-crystal systems, while a heterosynthon was observed in five systems. The combination of both homo- and heterosynthon was observed in three cocrystal systems. The phase transformation events were observed in most of the systems. In nine co-crystal systems, the melting points were observed intermediate between those of the API and the coformers.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: Bruker SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015). Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018) for (Id), KA1036_0m_Def-cat_2_3, KA955_0m_def-cat_1_1_form1, KA1027_0m_4def-cat_1_1_form2, KA951_0mdef-res_2_1, KA1018_0m_def-res_1_1, KA773_0m_def-phg_2_1, KA1017_0m_def-phghyd_2_1_2, KA803_0m_def-pyro_1_2, KA1032_0m_def-pyro_2_4; SHELXL2014 (Sheldrick, 2015) for Def-cat_1_2, KA254_0M_def-hq_1_0.5. For all structures, molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: Bruker SHELXTL.

(Id)

Crystal data

C7H9NO2	Dx = 1.456 Mg m^−3
Mr = 139.15	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9953 reflections
a = 13.70079 (19) Å	θ = 2.2–30.6°
b = 7.16238 (10) Å	µ = 0.11 mm^−1
c = 25.8688 (4) Å	T = 100 K
V = 2538.51 (6) Å^3	Block, colorless
Z = 16	0.32 × 0.28 × 0.16 mm
F(000) = 1184

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	3243 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.033
ω and φ scans	θmax = 30.6°, θmin = 2.2°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −19→13
Tmin = 0.686, Tmax = 0.746	k = −10→8
18090 measured reflections	l = −36→36
3892 independent reflections

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) + (0.0572P)^2 + 1.1028P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3892 reflections	Δρmax = 0.47 e Å^−3
193 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
C1A	0.21728 (7)	0.62677 (14)	0.40135 (3)	0.00954 (18)
C2A	0.31652 (7)	0.61778 (14)	0.39406 (3)	0.00989 (19)
C3A	0.38516 (7)	0.66671 (14)	0.43395 (4)	0.01034 (19)
C4A	0.34209 (8)	0.71939 (16)	0.48193 (4)	0.0125 (2)
H4A	0.383001	0.748526	0.510465	0.015*
C5A	0.24323 (8)	0.72877 (15)	0.48765 (4)	0.0120 (2)
H5A	0.216874	0.767039	0.519925	0.014*
C6A	0.07595 (7)	0.69611 (16)	0.45748 (4)	0.0143 (2)
H6AA	0.046317	0.778195	0.431553	0.021*
H6AB	0.063665	0.746489	0.492097	0.021*
H6AC	0.047350	0.571088	0.454761	0.021*
C7A	0.14580 (8)	0.57642 (15)	0.35975 (4)	0.0126 (2)
H7AA	0.107538	0.686930	0.350352	0.019*
H7AB	0.101953	0.478425	0.372389	0.019*
H7AC	0.181177	0.531003	0.329324	0.019*
O1A	0.35166 (6)	0.56375 (11)	0.34700 (3)	0.01343 (17)
H1O	0.4160 (13)	0.541 (3)	0.3497 (7)	0.036 (5)*
O2A	0.47635 (5)	0.66402 (12)	0.42541 (3)	0.01489 (17)
N1A	0.18170 (6)	0.68496 (12)	0.44853 (3)	0.01016 (17)
C1B	0.78598 (7)	0.46177 (14)	0.34963 (4)	0.00977 (19)
C2B	0.68662 (7)	0.47054 (14)	0.35668 (3)	0.00965 (19)
C3B	0.61827 (7)	0.41306 (14)	0.31736 (4)	0.01006 (19)
C4B	0.66177 (8)	0.35314 (15)	0.27017 (4)	0.01127 (19)
H4B	0.621243	0.313886	0.242421	0.014*
C5B	0.76071 (8)	0.35123 (15)	0.26419 (4)	0.01177 (19)
H5B	0.787378	0.312561	0.232023	0.014*
C6B	0.92792 (8)	0.39829 (16)	0.29339 (4)	0.0149 (2)
H6BA	0.940519	0.364649	0.257286	0.022*
H6BB	0.958114	0.305606	0.316218	0.022*
H6BC	0.955687	0.521705	0.300548	0.022*
C7B	0.85682 (8)	0.51145 (15)	0.39161 (4)	0.0127 (2)
H7BA	0.898474	0.403569	0.399113	0.019*
H7BB	0.820857	0.546837	0.422856	0.019*
H7BC	0.897432	0.616411	0.380298	0.019*
O1B	0.65159 (6)	0.52954 (12)	0.40310 (3)	0.01335 (16)
H2O	0.5858 (14)	0.547 (3)	0.4017 (7)	0.043 (5)*
O2B	0.52702 (5)	0.41437 (11)	0.32617 (3)	0.01374 (17)
N1B	0.82201 (6)	0.40264 (12)	0.30260 (3)	0.01037 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0101 (4)	0.0093 (4)	0.0092 (4)	0.0002 (4)	0.0003 (3)	0.0000 (3)
C2A	0.0104 (4)	0.0110 (4)	0.0083 (4)	0.0002 (4)	0.0009 (3)	−0.0004 (3)
C3A	0.0097 (5)	0.0108 (4)	0.0105 (4)	−0.0005 (3)	0.0004 (3)	−0.0012 (3)
C4A	0.0113 (5)	0.0167 (5)	0.0095 (4)	−0.0010 (4)	−0.0001 (3)	−0.0029 (3)
C5A	0.0119 (5)	0.0147 (5)	0.0095 (4)	−0.0012 (4)	0.0015 (3)	−0.0022 (3)
C6A	0.0072 (4)	0.0193 (5)	0.0163 (4)	0.0005 (4)	0.0025 (3)	−0.0013 (4)
C7A	0.0115 (5)	0.0147 (5)	0.0115 (4)	0.0003 (4)	−0.0028 (3)	−0.0007 (3)
O1A	0.0100 (4)	0.0208 (4)	0.0095 (3)	0.0018 (3)	0.0015 (2)	−0.0044 (3)
O2A	0.0076 (4)	0.0212 (4)	0.0159 (3)	−0.0002 (3)	0.0019 (3)	−0.0049 (3)
N1A	0.0077 (4)	0.0125 (4)	0.0103 (3)	−0.0002 (3)	0.0016 (3)	−0.0011 (3)
C1B	0.0104 (4)	0.0094 (4)	0.0095 (4)	0.0008 (4)	−0.0002 (3)	−0.0002 (3)
C2B	0.0102 (4)	0.0105 (4)	0.0082 (4)	0.0002 (3)	0.0007 (3)	−0.0010 (3)
C3B	0.0098 (4)	0.0107 (4)	0.0097 (4)	0.0003 (3)	−0.0001 (3)	0.0005 (3)
C4B	0.0117 (5)	0.0134 (5)	0.0087 (4)	0.0004 (4)	−0.0004 (3)	−0.0012 (3)
C5B	0.0128 (5)	0.0133 (5)	0.0092 (4)	0.0010 (4)	0.0009 (3)	−0.0001 (3)
C6B	0.0082 (4)	0.0203 (5)	0.0163 (4)	0.0016 (4)	0.0032 (3)	−0.0001 (4)
C7B	0.0099 (4)	0.0153 (5)	0.0127 (4)	0.0005 (4)	−0.0026 (3)	−0.0013 (4)
O1B	0.0092 (3)	0.0211 (4)	0.0097 (3)	0.0018 (3)	0.0012 (2)	−0.0045 (3)
O2B	0.0078 (3)	0.0192 (4)	0.0142 (3)	−0.0004 (3)	0.0005 (3)	−0.0029 (3)
N1B	0.0080 (4)	0.0128 (4)	0.0103 (3)	0.0003 (3)	0.0013 (3)	0.0006 (3)

Geometric parameters (Å, º)

C1A—C2A	1.3742 (14)	C1B—C2B	1.3749 (14)
C1A—N1A	1.3788 (12)	C1B—N1B	1.3796 (12)
C1A—C7A	1.4991 (13)	C1B—C7B	1.4992 (13)
C2A—O1A	1.3652 (11)	C2B—O1B	1.3605 (11)
C2A—C3A	1.4393 (13)	C2B—C3B	1.4425 (13)
C3A—O2A	1.2689 (12)	C3B—O2B	1.2708 (12)
C3A—C4A	1.4253 (13)	C3B—C4B	1.4248 (13)
C4A—C5A	1.3642 (15)	C4B—C5B	1.3645 (15)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—N1A	1.3540 (13)	C5B—N1B	1.3521 (13)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—N1A	1.4693 (13)	C6B—N1B	1.4708 (13)
C6A—H6AA	0.9800	C6B—H6BA	0.9800
C6A—H6AB	0.9800	C6B—H6BB	0.9800
C6A—H6AC	0.9800	C6B—H6BC	0.9800
C7A—H7AA	0.9800	C7B—H7BA	0.9800
C7A—H7AB	0.9800	C7B—H7BB	0.9800
C7A—H7AC	0.9800	C7B—H7BC	0.9800
O1A—H1O	0.899 (18)	O1B—H2O	0.911 (19)
C2A—C1A—N1A	119.05 (9)	C2B—C1B—N1B	119.02 (9)
C2A—C1A—C7A	122.45 (9)	C2B—C1B—C7B	122.28 (9)
N1A—C1A—C7A	118.50 (9)	N1B—C1B—C7B	118.69 (9)
O1A—C2A—C1A	118.98 (9)	O1B—C2B—C1B	118.72 (9)
O1A—C2A—C3A	118.55 (9)	O1B—C2B—C3B	118.81 (9)
C1A—C2A—C3A	122.46 (9)	C1B—C2B—C3B	122.43 (9)
O2A—C3A—C4A	124.28 (9)	O2B—C3B—C4B	124.56 (9)
O2A—C3A—C2A	120.99 (9)	O2B—C3B—C2B	120.68 (9)
C4A—C3A—C2A	114.73 (9)	C4B—C3B—C2B	114.75 (9)
C5A—C4A—C3A	121.23 (9)	C5B—C4B—C3B	121.04 (9)
C5A—C4A—H4A	119.4	C5B—C4B—H4B	119.5
C3A—C4A—H4A	119.4	C3B—C4B—H4B	119.5
N1A—C5A—C4A	121.72 (9)	N1B—C5B—C4B	122.08 (9)
N1A—C5A—H5A	119.1	N1B—C5B—H5B	119.0
C4A—C5A—H5A	119.1	C4B—C5B—H5B	119.0
N1A—C6A—H6AA	109.5	N1B—C6B—H6BA	109.5
N1A—C6A—H6AB	109.5	N1B—C6B—H6BB	109.5
H6AA—C6A—H6AB	109.5	H6BA—C6B—H6BB	109.5
N1A—C6A—H6AC	109.5	N1B—C6B—H6BC	109.5
H6AA—C6A—H6AC	109.5	H6BA—C6B—H6BC	109.5
H6AB—C6A—H6AC	109.5	H6BB—C6B—H6BC	109.5
C1A—C7A—H7AA	109.5	C1B—C7B—H7BA	109.5
C1A—C7A—H7AB	109.5	C1B—C7B—H7BB	109.5
H7AA—C7A—H7AB	109.5	H7BA—C7B—H7BB	109.5
C1A—C7A—H7AC	109.5	C1B—C7B—H7BC	109.5
H7AA—C7A—H7AC	109.5	H7BA—C7B—H7BC	109.5
H7AB—C7A—H7AC	109.5	H7BB—C7B—H7BC	109.5
C2A—O1A—H1O	109.0 (11)	C2B—O1B—H2O	110.8 (11)
C5A—N1A—C1A	120.76 (9)	C5B—N1B—C1B	120.63 (9)
C5A—N1A—C6A	118.92 (8)	C5B—N1B—C6B	119.21 (8)
C1A—N1A—C6A	120.30 (8)	C1B—N1B—C6B	120.15 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O···O2B	0.899 (18)	1.874 (18)	2.6847 (11)	149 (2)
O1B—H2O···O2A	0.911 (19)	1.825 (19)	2.6504 (11)	150 (2)
C6A—H6AB···O2A^i	0.98	2.53	3.4705 (12)	161
C7A—H7AA···O2B^ii	0.98	2.54	3.4957 (13)	165
C6B—H6BA···O2B^iii	0.98	2.49	3.3798 (12)	151
C7B—H7BA···O2A^iv	0.98	2.52	3.4901 (13)	171

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

(Def-cat_1_2)

Crystal data

C7H9NO2·2(C6H6O2)	Dx = 1.375 Mg m^−3
Mr = 359.37	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42/n	Cell parameters from 9989 reflections
a = 22.550 (4) Å	θ = 2.4–30.1°
c = 6.8267 (1) Å	µ = 0.10 mm^−1
V = 3471.42 (5) Å^3	T = 100 K
Z = 8	Needle, colorless
F(000) = 1520	0.28 × 0.12 × 0.09 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	4017 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.073
Absorption correction: multi-scan SADABS, Bruker, 2016	θmax = 30.6°, θmin = 2.6°
Tmin = 0.706, Tmax = 0.746	h = −32→26
47912 measured reflections	k = −32→32
5309 independent reflections	l = −9→9

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 2.1309P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
5309 reflections	Δρmax = 0.41 e Å^−3
257 parameters	Δρmin = −0.32 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	0.47835 (6)	0.66438 (6)	0.6865 (2)	0.0122 (3)
C2	0.49546 (6)	0.60852 (6)	0.6266 (2)	0.0113 (3)
C3	0.52343 (6)	0.56812 (6)	0.7564 (2)	0.0117 (3)
C4	0.52834 (7)	0.58639 (7)	0.9529 (2)	0.0150 (3)
H4	0.544184	0.560063	1.048095	0.018*
C5	0.51042 (7)	0.64178 (7)	1.0070 (2)	0.0154 (3)
H5	0.514663	0.653586	1.139891	0.018*
C6	0.46925 (7)	0.73987 (7)	0.9457 (2)	0.0192 (3)
H6A	0.489125	0.770035	0.865921	0.029*
H6B	0.480744	0.744772	1.083231	0.029*
H6C	0.426185	0.744369	0.933321	0.029*
C7	0.45202 (7)	0.70840 (7)	0.5480 (2)	0.0171 (3)
H7A	0.442144	0.688644	0.424357	0.026*
H7B	0.480697	0.740182	0.523120	0.026*
H7C	0.415963	0.725263	0.605587	0.026*
N1	0.48687 (5)	0.68024 (5)	0.87751 (18)	0.0129 (2)
O1	0.48697 (5)	0.59372 (5)	0.43606 (15)	0.0151 (2)
H1O	0.4866 (9)	0.5564 (10)	0.422 (3)	0.025 (5)*
O2	0.54424 (5)	0.51789 (4)	0.68932 (15)	0.0145 (2)
C8A	0.70093 (7)	0.59102 (7)	0.2529 (2)	0.0189 (3)
C9A	0.66270 (7)	0.58040 (7)	0.4104 (2)	0.0173 (3)
C10A	0.67482 (8)	0.60455 (8)	0.5928 (2)	0.0228 (3)
H10A	0.648727	0.597654	0.699700	0.027*
C11A	0.72541 (9)	0.63892 (9)	0.6184 (3)	0.0331 (4)
H11A	0.733905	0.655371	0.743351	0.040*
C12A	0.76343 (9)	0.64936 (10)	0.4634 (3)	0.0343 (5)
H12A	0.798036	0.672711	0.482156	0.041*
C13A	0.75091 (8)	0.62555 (8)	0.2797 (3)	0.0266 (4)
H13A	0.776764	0.633070	0.172717	0.032*
O3A	0.69064 (6)	0.56766 (6)	0.07146 (17)	0.0246 (3)
H2O	0.6607 (11)	0.5439 (11)	0.071 (3)	0.041 (7)*
O4A	0.61484 (5)	0.54393 (5)	0.37399 (17)	0.0201 (2)
H3O	0.5940 (10)	0.5356 (10)	0.481 (3)	0.037 (6)*
C8B	0.65264 (6)	0.39669 (7)	0.1487 (2)	0.0137 (3)
C9B	0.63404 (6)	0.42066 (6)	−0.0309 (2)	0.0124 (3)
C10B	0.64106 (6)	0.38840 (7)	−0.2019 (2)	0.0147 (3)
H10B	0.628714	0.404702	−0.323601	0.018*
C11B	0.66622 (7)	0.33209 (7)	−0.1954 (2)	0.0186 (3)
H11B	0.670998	0.309949	−0.312766	0.022*
C12B	0.68432 (7)	0.30827 (7)	−0.0182 (3)	0.0221 (3)
H12B	0.701553	0.269843	−0.014162	0.026*
C13B	0.67729 (7)	0.34046 (7)	0.1531 (2)	0.0190 (3)
H13B	0.689476	0.323842	0.274487	0.023*
O3B	0.64716 (5)	0.42727 (6)	0.31959 (16)	0.0201 (3)
H4O	0.6321 (11)	0.4639 (12)	0.297 (4)	0.048 (7)*
O4B	0.61048 (5)	0.47649 (5)	−0.02346 (16)	0.0186 (2)
H5O	0.5903 (10)	0.4857 (10)	−0.129 (4)	0.036 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0117 (6)	0.0131 (6)	0.0117 (6)	−0.0015 (5)	−0.0006 (5)	0.0005 (5)
C2	0.0117 (6)	0.0141 (6)	0.0082 (6)	−0.0015 (5)	−0.0006 (5)	−0.0002 (5)
C3	0.0123 (6)	0.0115 (6)	0.0111 (6)	0.0002 (5)	−0.0004 (5)	−0.0011 (5)
C4	0.0195 (7)	0.0165 (7)	0.0092 (7)	0.0029 (6)	−0.0021 (5)	0.0009 (5)
C5	0.0180 (7)	0.0191 (7)	0.0091 (6)	0.0010 (6)	−0.0011 (5)	−0.0025 (5)
C6	0.0234 (8)	0.0141 (7)	0.0201 (8)	0.0022 (6)	−0.0033 (6)	−0.0077 (6)
C7	0.0229 (8)	0.0128 (7)	0.0155 (7)	0.0021 (6)	−0.0025 (6)	0.0005 (5)
N1	0.0143 (6)	0.0120 (6)	0.0123 (6)	0.0001 (5)	−0.0003 (5)	−0.0029 (5)
O1	0.0235 (6)	0.0135 (5)	0.0082 (5)	0.0020 (4)	−0.0034 (4)	−0.0017 (4)
O2	0.0183 (5)	0.0135 (5)	0.0118 (5)	0.0037 (4)	−0.0024 (4)	−0.0020 (4)
C8A	0.0228 (8)	0.0214 (8)	0.0125 (7)	0.0051 (6)	−0.0009 (6)	−0.0005 (6)
C9A	0.0173 (7)	0.0205 (7)	0.0140 (7)	0.0035 (6)	−0.0003 (6)	−0.0014 (6)
C10A	0.0239 (8)	0.0291 (9)	0.0154 (7)	0.0003 (7)	0.0021 (6)	−0.0034 (6)
C11A	0.0356 (10)	0.0429 (11)	0.0207 (9)	−0.0115 (9)	0.0003 (8)	−0.0100 (8)
C12A	0.0324 (10)	0.0434 (11)	0.0270 (10)	−0.0161 (9)	0.0025 (8)	−0.0079 (8)
C13A	0.0262 (9)	0.0339 (10)	0.0198 (8)	−0.0036 (7)	0.0046 (7)	−0.0003 (7)
O3A	0.0254 (6)	0.0357 (7)	0.0126 (5)	−0.0032 (6)	0.0022 (5)	−0.0039 (5)
O4A	0.0178 (5)	0.0296 (6)	0.0130 (5)	−0.0013 (5)	0.0025 (4)	−0.0050 (5)
C8B	0.0099 (6)	0.0209 (7)	0.0101 (6)	−0.0026 (5)	−0.0022 (5)	0.0015 (5)
C9B	0.0099 (6)	0.0154 (7)	0.0118 (7)	−0.0002 (5)	−0.0019 (5)	0.0017 (5)
C10B	0.0128 (6)	0.0201 (7)	0.0111 (7)	−0.0005 (5)	−0.0012 (5)	0.0004 (6)
C11B	0.0157 (7)	0.0202 (7)	0.0199 (7)	0.0009 (6)	−0.0004 (6)	−0.0053 (6)
C12B	0.0188 (8)	0.0158 (7)	0.0316 (9)	0.0022 (6)	−0.0068 (7)	0.0001 (7)
C13B	0.0169 (7)	0.0207 (8)	0.0193 (8)	−0.0018 (6)	−0.0072 (6)	0.0067 (6)
O3B	0.0220 (6)	0.0287 (6)	0.0095 (5)	0.0004 (5)	−0.0035 (4)	−0.0011 (4)
O4B	0.0256 (6)	0.0169 (5)	0.0135 (5)	0.0071 (4)	−0.0093 (4)	−0.0023 (4)

Geometric parameters (Å, º)

C1—N1	1.3655 (18)	C10A—C11A	1.390 (3)
C1—C2	1.380 (2)	C10A—H10A	0.9500
C1—C7	1.494 (2)	C11A—C12A	1.382 (3)
C2—O1	1.3567 (17)	C11A—H11A	0.9500
C2—C3	1.419 (2)	C12A—C13A	1.393 (3)
C3—O2	1.3089 (17)	C12A—H12A	0.9500
C3—C4	1.407 (2)	C13A—H13A	0.9500
C4—C5	1.364 (2)	O3A—H2O	0.86 (3)
C4—H4	0.9500	O4A—H3O	0.89 (2)
C5—N1	1.3477 (19)	C8B—O3B	1.3611 (18)
C5—H5	0.9500	C8B—C13B	1.385 (2)
C6—N1	1.4776 (19)	C8B—C9B	1.404 (2)
C6—H6A	0.9800	C9B—O4B	1.3674 (18)
C6—H6B	0.9800	C9B—C10B	1.385 (2)
C6—H6C	0.9800	C10B—C11B	1.391 (2)
C7—H7A	0.9800	C10B—H10B	0.9500
C7—H7B	0.9800	C11B—C12B	1.385 (2)
C7—H7C	0.9800	C11B—H11B	0.9500
O1—H1O	0.85 (2)	C12B—C13B	1.386 (2)
C8A—O3A	1.3658 (19)	C12B—H12B	0.9500
C8A—C13A	1.382 (2)	C13B—H13B	0.9500
C8A—C9A	1.399 (2)	O3B—H4O	0.91 (3)
C9A—O4A	1.3794 (19)	O4B—H5O	0.88 (2)
C9A—C10A	1.387 (2)
N1—C1—C2	118.87 (13)	C10A—C9A—C8A	120.11 (15)
N1—C1—C7	119.10 (13)	C9A—C10A—C11A	119.56 (16)
C2—C1—C7	122.02 (13)	C9A—C10A—H10A	120.2
O1—C2—C1	118.00 (13)	C11A—C10A—H10A	120.2
O1—C2—C3	120.25 (13)	C12A—C11A—C10A	120.56 (17)
C1—C2—C3	121.70 (13)	C12A—C11A—H11A	119.7
O2—C3—C4	123.97 (13)	C10A—C11A—H11A	119.7
O2—C3—C2	119.76 (13)	C11A—C12A—C13A	119.84 (17)
C4—C3—C2	116.24 (13)	C11A—C12A—H12A	120.1
C5—C4—C3	120.21 (13)	C13A—C12A—H12A	120.1
C5—C4—H4	119.9	C8A—C13A—C12A	120.12 (16)
C3—C4—H4	119.9	C8A—C13A—H13A	119.9
N1—C5—C4	121.89 (14)	C12A—C13A—H13A	119.9
N1—C5—H5	119.1	C8A—O3A—H2O	112.0 (16)
C4—C5—H5	119.1	C9A—O4A—H3O	113.0 (15)
N1—C6—H6A	109.5	O3B—C8B—C13B	118.78 (13)
N1—C6—H6B	109.5	O3B—C8B—C9B	121.76 (13)
H6A—C6—H6B	109.5	C13B—C8B—C9B	119.46 (14)
N1—C6—H6C	109.5	O4B—C9B—C10B	124.00 (13)
H6A—C6—H6C	109.5	O4B—C9B—C8B	116.01 (13)
H6B—C6—H6C	109.5	C10B—C9B—C8B	119.98 (13)
C1—C7—H7A	109.5	C9B—C10B—C11B	119.94 (14)
C1—C7—H7B	109.5	C9B—C10B—H10B	120.0
H7A—C7—H7B	109.5	C11B—C10B—H10B	120.0
C1—C7—H7C	109.5	C12B—C11B—C10B	120.13 (15)
H7A—C7—H7C	109.5	C12B—C11B—H11B	119.9
H7B—C7—H7C	109.5	C10B—C11B—H11B	119.9
C5—N1—C1	120.89 (12)	C11B—C12B—C13B	120.02 (15)
C5—N1—C6	119.00 (12)	C11B—C12B—H12B	120.0
C1—N1—C6	120.10 (12)	C13B—C12B—H12B	120.0
C2—O1—H1O	110.6 (14)	C8B—C13B—C12B	120.47 (14)
O3A—C8A—C13A	118.43 (15)	C8B—C13B—H13B	119.8
O3A—C8A—C9A	121.76 (15)	C12B—C13B—H13B	119.8
C13A—C8A—C9A	119.81 (15)	C8B—O3B—H4O	110.4 (17)
O4A—C9A—C10A	123.38 (14)	C9B—O4B—H5O	112.8 (15)
O4A—C9A—C8A	116.47 (13)
N1—C1—C2—O1	−179.60 (12)	C13A—C8A—C9A—C10A	0.2 (2)
C7—C1—C2—O1	−0.9 (2)	O4A—C9A—C10A—C11A	177.38 (16)
N1—C1—C2—C3	−2.2 (2)	C8A—C9A—C10A—C11A	−0.5 (3)
C7—C1—C2—C3	176.45 (13)	C9A—C10A—C11A—C12A	0.3 (3)
O1—C2—C3—O2	4.1 (2)	C10A—C11A—C12A—C13A	0.3 (3)
C1—C2—C3—O2	−173.26 (13)	O3A—C8A—C13A—C12A	−178.94 (17)
O1—C2—C3—C4	−177.70 (13)	C9A—C8A—C13A—C12A	0.5 (3)
C1—C2—C3—C4	5.0 (2)	C11A—C12A—C13A—C8A	−0.7 (3)
O2—C3—C4—C5	173.81 (14)	O3B—C8B—C9B—O4B	0.3 (2)
C2—C3—C4—C5	−4.3 (2)	C13B—C8B—C9B—O4B	−179.63 (13)
C3—C4—C5—N1	1.0 (2)	O3B—C8B—C9B—C10B	179.19 (13)
C4—C5—N1—C1	2.0 (2)	C13B—C8B—C9B—C10B	−0.8 (2)
C4—C5—N1—C6	−179.08 (14)	O4B—C9B—C10B—C11B	179.17 (14)
C2—C1—N1—C5	−1.4 (2)	C8B—C9B—C10B—C11B	0.4 (2)
C7—C1—N1—C5	179.92 (14)	C9B—C10B—C11B—C12B	−0.1 (2)
C2—C1—N1—C6	179.70 (13)	C10B—C11B—C12B—C13B	0.1 (2)
C7—C1—N1—C6	1.0 (2)	O3B—C8B—C13B—C12B	−179.14 (14)
O3A—C8A—C9A—O4A	1.5 (2)	C9B—C8B—C13B—C12B	0.8 (2)
C13A—C8A—C9A—O4A	−177.90 (15)	C11B—C12B—C13B—C8B	−0.5 (2)
O3A—C8A—C9A—C10A	179.55 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.85 (2)	1.97 (2)	2.7499 (15)	153.2 (19)
O4A—H3O···O2	0.89 (2)	1.86 (2)	2.7410 (16)	175 (2)
O3B—H4O···O4A	0.91 (3)	1.92 (3)	2.7550 (18)	152 (2)
O3B—H4O···O4B	0.91 (3)	2.26 (3)	2.7205 (16)	111 (2)
O4B—H5O···O2^ii	0.88 (2)	1.77 (2)	2.6358 (15)	167 (2)
C5—H5···O1^iii	0.95	2.51	3.1673 (18)	126
C10B—H10B···O3B^ii	0.95	2.52	3.3847 (18)	151

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

Deferiprone-Catechol (2:3) cocrystal (KA1036_0m_Def-cat_2_3)

Crystal data

2(C7H9NO2)·3(C6H6O2)	F(000) = 644
Mr = 608.63	Dx = 1.396 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 6.9488 (17) Å	Cell parameters from 9899 reflections
b = 9.982 (2) Å	θ = 2.8–30.6°
c = 20.881 (5) Å	µ = 0.10 mm^−1
β = 90.927 (7)°	T = 100 K
V = 1448.3 (6) Å^3	Block, colorless
Z = 2	0.32 × 0.28 × 0.21 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	8447 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.049
ω and φ scans	θmax = 30.6°, θmin = 2.3°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −9→9
Tmin = 0.649, Tmax = 0.746	k = −14→14
34096 measured reflections	l = −29→29
8799 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.062	w = 1/[σ^2(Fo^2) + (0.0525P)^2 + 2.4574P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.168	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.41 e Å^−3
8799 reflections	Δρmin = −0.41 e Å^−3
458 parameters	Absolute structure: Flack x determined using 3652 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: 0.3 (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	Occ. (<1)
C1A	0.2719 (5)	0.6492 (4)	0.13991 (16)	0.0161 (6)
C2A	0.3566 (5)	0.5416 (4)	0.16957 (16)	0.0146 (6)
C3A	0.2540 (5)	0.4203 (4)	0.18182 (16)	0.0156 (6)
C4A	0.0574 (6)	0.4202 (5)	0.16367 (19)	0.0225 (8)
H4A	−0.018600	0.342786	0.170995	0.027*
C5A	−0.0237 (6)	0.5296 (5)	0.13590 (19)	0.0245 (8)
H5A	−0.157042	0.528008	0.125068	0.029*
C6A	−0.0145 (7)	0.7561 (5)	0.0917 (2)	0.0307 (10)
H6AA	0.057348	0.781428	0.053522	0.046*
H6AB	−0.017871	0.831972	0.121405	0.046*
H6AC	−0.146191	0.731242	0.079099	0.046*
C7A	0.3843 (6)	0.7723 (4)	0.12293 (18)	0.0207 (7)
H7AA	0.398524	0.776876	0.076360	0.031*
H7AB	0.511831	0.768415	0.143572	0.031*
H7AC	0.315875	0.852083	0.137759	0.031*
N1A	0.0803 (5)	0.6417 (4)	0.12308 (15)	0.0206 (6)
O1A	0.5481 (4)	0.5482 (3)	0.18441 (13)	0.0168 (5)
H1A	0.575399	0.490481	0.212363	0.025*
O2A	0.3434 (4)	0.3174 (3)	0.20574 (13)	0.0196 (5)
C1B	0.7093 (5)	0.1151 (3)	0.36593 (15)	0.0109 (5)
C2B	0.6458 (5)	0.2298 (3)	0.33367 (16)	0.0108 (6)
C3B	0.7742 (4)	0.3371 (3)	0.31883 (15)	0.0098 (5)
C4B	0.9709 (5)	0.3156 (3)	0.33511 (16)	0.0124 (6)
H4B	1.064066	0.381066	0.324301	0.015*
C5B	1.0272 (5)	0.2012 (3)	0.36626 (17)	0.0125 (6)
H5B	1.159657	0.188761	0.376540	0.015*
C6B	0.9695 (5)	−0.0134 (4)	0.41889 (18)	0.0166 (7)
H6BA	0.939460	−0.094763	0.394401	0.025*
H6BB	0.905816	−0.017344	0.460390	0.025*
H6BC	1.108990	−0.006843	0.425731	0.025*
C7B	0.5733 (5)	0.0055 (3)	0.38372 (17)	0.0137 (6)
H7BA	0.449223	0.019581	0.361799	0.021*
H7BB	0.554977	0.006148	0.430148	0.021*
H7BC	0.626807	−0.081103	0.370848	0.021*
N1B	0.9001 (4)	0.1054 (3)	0.38284 (14)	0.0113 (5)
O1B	0.4544 (3)	0.2388 (3)	0.32002 (12)	0.0138 (5)
H1B	0.437990	0.277578	0.284660	0.021*
O2B	0.7103 (3)	0.4468 (2)	0.29240 (12)	0.0111 (4)
C8A	0.1347 (5)	0.8348 (4)	0.26655 (15)	0.0129 (6)
C9A	−0.0287 (5)	0.7535 (3)	0.27123 (15)	0.0114 (6)
C10A	−0.2105 (5)	0.8043 (4)	0.25475 (17)	0.0145 (6)
H10A	−0.321524	0.749479	0.258468	0.017*
C11A	−0.2280 (5)	0.9356 (4)	0.23287 (18)	0.0174 (7)
H11A	−0.350870	0.969958	0.220901	0.021*
C12A	−0.0659 (6)	1.0165 (4)	0.22850 (18)	0.0185 (7)
H12A	−0.079036	1.106277	0.213931	0.022*
C13A	0.1167 (5)	0.9669 (4)	0.24540 (17)	0.0156 (6)
H13A	0.227117	1.022576	0.242472	0.019*
O3A	0.3152 (4)	0.7880 (3)	0.28248 (13)	0.0173 (5)
H3A	0.305761	0.712549	0.299998	0.026*
O4A	0.0018 (3)	0.6260 (2)	0.29408 (12)	0.0133 (4)
H4A1	−0.102005	0.582892	0.292445	0.020*
C8B	0.3178 (5)	0.6869 (3)	0.44165 (16)	0.0124 (6)
C9B	0.4664 (5)	0.6240 (3)	0.40733 (15)	0.0116 (6)
C10B	0.6558 (5)	0.6363 (4)	0.42883 (16)	0.0138 (6)
H10B	0.756010	0.593042	0.406365	0.017*
C11B	0.6995 (5)	0.7125 (4)	0.48363 (16)	0.0141 (6)
H11B	0.829099	0.720224	0.498365	0.017*
C12B	0.5536 (5)	0.7765 (4)	0.51627 (16)	0.0156 (6)
H12B	0.583573	0.829442	0.552886	0.019*
C13B	0.3626 (5)	0.7631 (4)	0.49536 (17)	0.0147 (6)
H13B	0.262921	0.806361	0.518072	0.018*
O3B	0.1290 (4)	0.6730 (3)	0.42250 (13)	0.0171 (5)
H3B	0.123517	0.631489	0.387518	0.026*
O4B	0.4100 (3)	0.5544 (3)	0.35333 (12)	0.0144 (5)
H4B1	0.507579	0.524566	0.334864	0.022*
C8C	0.5575 (8)	0.1394 (6)	0.0863 (3)	0.0158 (17)	0.578 (7)
C9C	0.3632 (8)	0.1287 (7)	0.0702 (3)	0.0193 (19)	0.578 (7)
H9C	0.270146	0.175277	0.094530	0.023*	0.578 (7)
C10C	0.3050 (8)	0.0501 (6)	0.0185 (2)	0.0226 (16)	0.578 (7)
H10C	0.172198	0.042817	0.007483	0.027*	0.578 (7)
C11C	0.4411 (10)	−0.0180 (5)	−0.0171 (2)	0.0217 (15)	0.578 (7)
H11C	0.401318	−0.071790	−0.052472	0.026*	0.578 (7)
C12C	0.6354 (10)	−0.0074 (6)	−0.0010 (2)	0.0229 (16)	0.578 (7)
H12C	0.728388	−0.053938	−0.025380	0.028*	0.578 (7)
C13C	0.6936 (7)	0.0713 (6)	0.0507 (3)	0.0206 (15)	0.578 (7)
O3C	0.6313 (7)	0.2146 (5)	0.1371 (2)	0.0194 (11)	0.578 (7)
H3C	0.567557	0.285703	0.140539	0.029*	0.578 (7)
O4C	0.8821 (10)	0.0792 (8)	0.0632 (4)	0.0418 (18)	0.578 (7)
H4C	0.911084	0.026615	0.093299	0.063*	0.578 (7)
C8'	0.4207 (10)	0.1138 (10)	0.0776 (4)	0.017 (3)	0.422 (7)
C9'	0.3890 (10)	0.0332 (8)	0.0242 (3)	0.018 (2)	0.422 (7)
C10'	0.5441 (13)	−0.0140 (7)	−0.0104 (3)	0.019 (2)	0.422 (7)
H10'	0.522448	−0.069134	−0.046929	0.023*	0.422 (7)
C11'	0.7308 (11)	0.0194 (8)	0.0083 (3)	0.025 (2)	0.422 (7)
H11'	0.836817	−0.012902	−0.015340	0.030*	0.422 (7)
C12'	0.7625 (10)	0.1000 (9)	0.0617 (4)	0.022 (2)	0.422 (7)
H12'	0.890119	0.122834	0.074571	0.027*	0.422 (7)
C13'	0.6074 (12)	0.1472 (10)	0.0964 (4)	0.022 (3)	0.422 (7)
H13'	0.629050	0.202340	0.132894	0.027*	0.422 (7)
O3'	0.2566 (9)	0.1517 (7)	0.1107 (3)	0.0198 (15)	0.422 (7)
H3'	0.288568	0.200047	0.142011	0.030*	0.422 (7)
O4'	0.2137 (13)	−0.0044 (9)	0.0049 (4)	0.033 (2)	0.422 (7)
H4'	0.131371	0.046055	0.021380	0.049*	0.422 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0151 (15)	0.0208 (17)	0.0123 (14)	0.0005 (13)	−0.0009 (11)	−0.0011 (13)
C2A	0.0134 (15)	0.0190 (16)	0.0112 (13)	−0.0018 (12)	−0.0013 (11)	−0.0009 (12)
C3A	0.0175 (15)	0.0209 (17)	0.0085 (13)	−0.0051 (13)	−0.0002 (11)	−0.0001 (12)
C4A	0.0164 (16)	0.032 (2)	0.0186 (17)	−0.0121 (15)	−0.0005 (13)	0.0004 (15)
C5A	0.0114 (15)	0.043 (2)	0.0195 (17)	−0.0036 (15)	−0.0014 (13)	−0.0004 (16)
C6A	0.028 (2)	0.039 (2)	0.0247 (19)	0.0151 (19)	−0.0063 (16)	0.0051 (18)
C7A	0.0240 (18)	0.0203 (17)	0.0177 (16)	0.0004 (14)	−0.0020 (13)	0.0034 (14)
N1A	0.0143 (14)	0.0321 (18)	0.0152 (13)	0.0059 (13)	−0.0020 (11)	0.0035 (13)
O1A	0.0130 (11)	0.0200 (12)	0.0173 (12)	−0.0045 (10)	−0.0053 (9)	0.0062 (10)
O2A	0.0253 (13)	0.0184 (13)	0.0150 (11)	−0.0048 (10)	−0.0040 (10)	0.0017 (10)
C1B	0.0116 (13)	0.0100 (13)	0.0111 (13)	−0.0007 (11)	−0.0007 (10)	0.0010 (11)
C2B	0.0097 (13)	0.0094 (13)	0.0135 (13)	−0.0010 (10)	−0.0005 (10)	−0.0002 (11)
C3B	0.0091 (13)	0.0100 (13)	0.0102 (13)	−0.0005 (11)	−0.0023 (10)	−0.0007 (11)
C4B	0.0098 (13)	0.0114 (14)	0.0158 (14)	−0.0012 (11)	−0.0012 (11)	−0.0002 (11)
C5B	0.0074 (13)	0.0132 (14)	0.0170 (14)	0.0000 (11)	−0.0010 (10)	0.0003 (11)
C6B	0.0166 (16)	0.0121 (14)	0.0209 (16)	0.0036 (12)	−0.0037 (13)	0.0062 (12)
C7B	0.0147 (15)	0.0089 (13)	0.0175 (15)	−0.0026 (11)	0.0015 (12)	0.0029 (11)
N1B	0.0107 (12)	0.0082 (12)	0.0150 (12)	0.0012 (9)	−0.0016 (10)	0.0006 (10)
O1B	0.0089 (10)	0.0155 (11)	0.0170 (11)	−0.0019 (8)	−0.0025 (8)	0.0054 (9)
O2B	0.0102 (10)	0.0090 (10)	0.0141 (10)	0.0006 (8)	−0.0012 (8)	0.0018 (8)
C8A	0.0126 (14)	0.0152 (15)	0.0106 (13)	−0.0032 (12)	−0.0029 (11)	−0.0009 (11)
C9A	0.0146 (14)	0.0093 (13)	0.0103 (13)	−0.0017 (11)	−0.0028 (11)	0.0009 (10)
C10A	0.0127 (14)	0.0145 (15)	0.0162 (14)	−0.0012 (12)	−0.0014 (11)	−0.0030 (12)
C11A	0.0165 (15)	0.0174 (16)	0.0183 (15)	0.0042 (13)	−0.0038 (12)	−0.0001 (13)
C12A	0.0244 (18)	0.0112 (14)	0.0199 (16)	0.0006 (13)	−0.0032 (14)	0.0026 (12)
C13A	0.0180 (15)	0.0144 (15)	0.0144 (14)	−0.0044 (12)	0.0000 (12)	−0.0007 (12)
O3A	0.0096 (11)	0.0167 (12)	0.0256 (13)	−0.0027 (9)	−0.0018 (9)	0.0011 (10)
O4A	0.0122 (10)	0.0102 (10)	0.0174 (11)	−0.0031 (8)	−0.0040 (8)	0.0031 (9)
C8B	0.0111 (14)	0.0125 (14)	0.0136 (14)	0.0005 (11)	0.0002 (11)	0.0030 (11)
C9B	0.0116 (13)	0.0103 (13)	0.0128 (13)	−0.0008 (11)	−0.0017 (11)	−0.0001 (11)
C10B	0.0114 (14)	0.0145 (14)	0.0154 (14)	0.0019 (11)	−0.0012 (11)	0.0021 (12)
C11B	0.0135 (14)	0.0156 (15)	0.0130 (14)	−0.0011 (12)	−0.0022 (11)	0.0037 (12)
C12B	0.0191 (16)	0.0171 (16)	0.0106 (13)	0.0007 (13)	−0.0006 (11)	0.0026 (12)
C13B	0.0144 (15)	0.0150 (15)	0.0146 (14)	0.0031 (12)	0.0017 (11)	0.0009 (12)
O3B	0.0096 (11)	0.0249 (14)	0.0166 (12)	0.0027 (9)	−0.0014 (9)	−0.0023 (10)
O4B	0.0101 (10)	0.0158 (11)	0.0174 (11)	0.0029 (9)	−0.0017 (8)	−0.0061 (9)
C8C	0.019 (4)	0.015 (3)	0.012 (3)	0.003 (3)	−0.002 (3)	0.003 (2)
C9C	0.021 (4)	0.015 (4)	0.023 (4)	0.001 (3)	−0.001 (3)	−0.003 (3)
C10C	0.024 (4)	0.026 (4)	0.017 (3)	−0.010 (4)	−0.006 (3)	−0.001 (3)
C11C	0.038 (5)	0.016 (3)	0.011 (3)	−0.002 (3)	−0.002 (3)	0.002 (2)
C12C	0.030 (5)	0.023 (4)	0.015 (3)	0.005 (4)	0.000 (4)	0.004 (3)
C13C	0.016 (4)	0.026 (4)	0.020 (3)	0.006 (3)	0.000 (3)	0.008 (3)
O3C	0.013 (2)	0.021 (2)	0.024 (2)	0.0017 (17)	−0.0078 (17)	−0.0045 (19)
O4C	0.027 (3)	0.050 (4)	0.048 (4)	0.003 (3)	−0.011 (3)	−0.005 (3)
C8'	0.029 (7)	0.012 (4)	0.012 (4)	0.006 (5)	0.002 (4)	−0.002 (3)
C9'	0.020 (5)	0.016 (4)	0.018 (4)	−0.003 (4)	−0.003 (4)	0.007 (3)
C10'	0.025 (6)	0.019 (4)	0.014 (4)	−0.005 (5)	−0.001 (5)	−0.001 (3)
C11'	0.021 (5)	0.029 (5)	0.024 (5)	0.002 (4)	0.002 (4)	0.007 (4)
C12'	0.005 (5)	0.036 (6)	0.026 (5)	0.001 (4)	−0.002 (4)	0.001 (4)
C13'	0.022 (6)	0.025 (5)	0.020 (5)	0.001 (4)	−0.003 (4)	0.007 (4)
O3'	0.016 (3)	0.025 (3)	0.019 (3)	−0.003 (2)	0.005 (2)	−0.009 (2)
O4'	0.032 (4)	0.040 (5)	0.026 (4)	0.001 (4)	−0.001 (3)	−0.004 (3)

Geometric parameters (Å, º)

C1A—C2A	1.369 (5)	C12A—C13A	1.403 (5)
C1A—N1A	1.374 (4)	C12A—H12A	0.9500
C1A—C7A	1.501 (5)	C13A—H13A	0.9500
C2A—O1A	1.363 (4)	O3A—H3A	0.8400
C2A—C3A	1.430 (5)	O4A—H4A1	0.8400
C3A—O2A	1.296 (5)	C8B—O3B	1.372 (4)
C3A—C4A	1.411 (5)	C8B—C13B	1.386 (5)
C4A—C5A	1.355 (6)	C8B—C9B	1.414 (5)
C4A—H4A	0.9500	C9B—O4B	1.376 (4)
C5A—N1A	1.362 (6)	C9B—C10B	1.389 (4)
C5A—H5A	0.9500	C10B—C11B	1.403 (5)
C6A—N1A	1.467 (6)	C10B—H10B	0.9500
C6A—H6AA	0.9800	C11B—C12B	1.387 (5)
C6A—H6AB	0.9800	C11B—H11B	0.9500
C6A—H6AC	0.9800	C12B—C13B	1.397 (5)
C7A—H7AA	0.9800	C12B—H12B	0.9500
C7A—H7AB	0.9800	C13B—H13B	0.9500
C7A—H7AC	0.9800	O3B—H3B	0.8400
O1A—H1A	0.8400	O4B—H4B1	0.8400
C1B—N1B	1.370 (4)	C8C—C9C	1.3900
C1B—C2B	1.397 (4)	C8C—C13C	1.3900
C1B—C7B	1.496 (5)	C8C—O3C	1.391 (6)
C2B—O1B	1.358 (4)	C9C—C10C	1.3900
C2B—C3B	1.431 (4)	C9C—H9C	0.9500
C3B—O2B	1.301 (4)	C10C—C11C	1.3900
C3B—C4B	1.419 (4)	C10C—H10C	0.9500
C4B—C5B	1.368 (5)	C11C—C12C	1.3900
C4B—H4B	0.9500	C11C—H11C	0.9500
C5B—N1B	1.351 (4)	C12C—C13C	1.3900
C5B—H5B	0.9500	C12C—H12C	0.9500
C6B—N1B	1.481 (4)	C13C—O4C	1.334 (8)
C6B—H6BA	0.9800	O3C—H3C	0.8400
C6B—H6BB	0.9800	O4C—H4C	0.8400
C6B—H6BC	0.9800	C8'—C9'	1.3900
C7B—H7BA	0.9800	C8'—C13'	1.3900
C7B—H7BB	0.9800	C8'—O3'	1.394 (8)
C7B—H7BC	0.9800	C9'—O4'	1.331 (11)
O1B—H1B	0.8400	C9'—C10'	1.3900
C8A—O3A	1.375 (4)	C10'—C11'	1.3900
C8A—C13A	1.395 (5)	C10'—H10'	0.9500
C8A—C9A	1.400 (4)	C11'—C12'	1.3900
C9A—O4A	1.375 (4)	C11'—H11'	0.9500
C9A—C10A	1.399 (5)	C12'—C13'	1.3900
C10A—C11A	1.393 (5)	C12'—H12'	0.9500
C10A—H10A	0.9500	C13'—H13'	0.9500
C11A—C12A	1.390 (5)	O3'—H3'	0.8400
C11A—H11A	0.9500	O4'—H4'	0.8400
C2A—C1A—N1A	118.7 (3)	C12A—C11A—C10A	120.1 (3)
C2A—C1A—C7A	121.9 (3)	C12A—C11A—H11A	119.9
N1A—C1A—C7A	119.3 (3)	C10A—C11A—H11A	119.9
O1A—C2A—C1A	118.4 (3)	C11A—C12A—C13A	120.6 (3)
O1A—C2A—C3A	119.2 (3)	C11A—C12A—H12A	119.7
C1A—C2A—C3A	122.3 (3)	C13A—C12A—H12A	119.7
O2A—C3A—C4A	124.0 (3)	C8A—C13A—C12A	119.3 (3)
O2A—C3A—C2A	120.1 (3)	C8A—C13A—H13A	120.4
C4A—C3A—C2A	115.8 (3)	C12A—C13A—H13A	120.4
C5A—C4A—C3A	120.6 (4)	C8A—O3A—H3A	109.5
C5A—C4A—H4A	119.7	C9A—O4A—H4A1	109.5
C3A—C4A—H4A	119.7	O3B—C8B—C13B	119.5 (3)
C4A—C5A—N1A	121.9 (3)	O3B—C8B—C9B	120.7 (3)
C4A—C5A—H5A	119.1	C13B—C8B—C9B	119.8 (3)
N1A—C5A—H5A	119.1	O4B—C9B—C10B	124.5 (3)
N1A—C6A—H6AA	109.5	O4B—C9B—C8B	116.0 (3)
N1A—C6A—H6AB	109.5	C10B—C9B—C8B	119.5 (3)
H6AA—C6A—H6AB	109.5	C9B—C10B—C11B	120.2 (3)
N1A—C6A—H6AC	109.5	C9B—C10B—H10B	119.9
H6AA—C6A—H6AC	109.5	C11B—C10B—H10B	119.9
H6AB—C6A—H6AC	109.5	C12B—C11B—C10B	120.0 (3)
C1A—C7A—H7AA	109.5	C12B—C11B—H11B	120.0
C1A—C7A—H7AB	109.5	C10B—C11B—H11B	120.0
H7AA—C7A—H7AB	109.5	C11B—C12B—C13B	120.1 (3)
C1A—C7A—H7AC	109.5	C11B—C12B—H12B	120.0
H7AA—C7A—H7AC	109.5	C13B—C12B—H12B	120.0
H7AB—C7A—H7AC	109.5	C8B—C13B—C12B	120.4 (3)
C5A—N1A—C1A	120.7 (3)	C8B—C13B—H13B	119.8
C5A—N1A—C6A	119.4 (3)	C12B—C13B—H13B	119.8
C1A—N1A—C6A	119.9 (4)	C8B—O3B—H3B	109.5
C2A—O1A—H1A	109.5	C9B—O4B—H4B1	109.5
N1B—C1B—C2B	118.6 (3)	C9C—C8C—C13C	120.0
N1B—C1B—C7B	119.8 (3)	C9C—C8C—O3C	124.8 (4)
C2B—C1B—C7B	121.6 (3)	C13C—C8C—O3C	115.2 (4)
O1B—C2B—C1B	117.1 (3)	C10C—C9C—C8C	120.0
O1B—C2B—C3B	121.1 (3)	C10C—C9C—H9C	120.0
C1B—C2B—C3B	121.7 (3)	C8C—C9C—H9C	120.0
O2B—C3B—C4B	123.3 (3)	C9C—C10C—C11C	120.0
O2B—C3B—C2B	120.8 (3)	C9C—C10C—H10C	120.0
C4B—C3B—C2B	115.9 (3)	C11C—C10C—H10C	120.0
C5B—C4B—C3B	120.5 (3)	C12C—C11C—C10C	120.0
C5B—C4B—H4B	119.8	C12C—C11C—H11C	120.0
C3B—C4B—H4B	119.8	C10C—C11C—H11C	120.0
N1B—C5B—C4B	122.0 (3)	C13C—C12C—C11C	120.0
N1B—C5B—H5B	119.0	C13C—C12C—H12C	120.0
C4B—C5B—H5B	119.0	C11C—C12C—H12C	120.0
N1B—C6B—H6BA	109.5	O4C—C13C—C12C	117.3 (5)
N1B—C6B—H6BB	109.5	O4C—C13C—C8C	122.7 (5)
H6BA—C6B—H6BB	109.5	C12C—C13C—C8C	120.0
N1B—C6B—H6BC	109.5	C8C—O3C—H3C	109.5
H6BA—C6B—H6BC	109.5	C13C—O4C—H4C	109.5
H6BB—C6B—H6BC	109.5	C9'—C8'—C13'	120.0
C1B—C7B—H7BA	109.5	C9'—C8'—O3'	115.7 (6)
C1B—C7B—H7BB	109.5	C13'—C8'—O3'	124.2 (6)
H7BA—C7B—H7BB	109.5	O4'—C9'—C10'	117.4 (6)
C1B—C7B—H7BC	109.5	O4'—C9'—C8'	122.6 (6)
H7BA—C7B—H7BC	109.5	C10'—C9'—C8'	120.0
H7BB—C7B—H7BC	109.5	C9'—C10'—C11'	120.0
C5B—N1B—C1B	121.2 (3)	C9'—C10'—H10'	120.0
C5B—N1B—C6B	119.2 (3)	C11'—C10'—H10'	120.0
C1B—N1B—C6B	119.6 (3)	C10'—C11'—C12'	120.0
C2B—O1B—H1B	109.5	C10'—C11'—H11'	120.0
O3A—C8A—C13A	118.3 (3)	C12'—C11'—H11'	120.0
O3A—C8A—C9A	121.6 (3)	C13'—C12'—C11'	120.0
C13A—C8A—C9A	120.1 (3)	C13'—C12'—H12'	120.0
O4A—C9A—C10A	123.7 (3)	C11'—C12'—H12'	120.0
O4A—C9A—C8A	116.1 (3)	C12'—C13'—C8'	120.0
C10A—C9A—C8A	120.2 (3)	C12'—C13'—H13'	120.0
C11A—C10A—C9A	119.7 (3)	C8'—C13'—H13'	120.0
C11A—C10A—H10A	120.2	C8'—O3'—H3'	109.5
C9A—C10A—H10A	120.2	C9'—O4'—H4'	109.5
N1A—C1A—C2A—O1A	178.1 (3)	C8A—C9A—C10A—C11A	0.8 (5)
C7A—C1A—C2A—O1A	0.7 (5)	C9A—C10A—C11A—C12A	−1.1 (5)
N1A—C1A—C2A—C3A	2.0 (5)	C10A—C11A—C12A—C13A	0.6 (6)
C7A—C1A—C2A—C3A	−175.4 (3)	O3A—C8A—C13A—C12A	179.6 (3)
O1A—C2A—C3A—O2A	−1.2 (5)	C9A—C8A—C13A—C12A	−0.5 (5)
C1A—C2A—C3A—O2A	174.9 (3)	C11A—C12A—C13A—C8A	0.2 (5)
O1A—C2A—C3A—C4A	−178.5 (3)	O3B—C8B—C9B—O4B	2.6 (5)
C1A—C2A—C3A—C4A	−2.4 (5)	C13B—C8B—C9B—O4B	−177.7 (3)
O2A—C3A—C4A—C5A	−176.6 (4)	O3B—C8B—C9B—C10B	−178.0 (3)
C2A—C3A—C4A—C5A	0.6 (5)	C13B—C8B—C9B—C10B	1.6 (5)
C3A—C4A—C5A—N1A	1.6 (6)	O4B—C9B—C10B—C11B	178.3 (3)
C4A—C5A—N1A—C1A	−2.1 (6)	C8B—C9B—C10B—C11B	−1.0 (5)
C4A—C5A—N1A—C6A	178.7 (4)	C9B—C10B—C11B—C12B	−0.4 (5)
C2A—C1A—N1A—C5A	0.3 (5)	C10B—C11B—C12B—C13B	1.2 (5)
C7A—C1A—N1A—C5A	177.8 (4)	O3B—C8B—C13B—C12B	178.8 (3)
C2A—C1A—N1A—C6A	179.5 (4)	C9B—C8B—C13B—C12B	−0.9 (5)
C7A—C1A—N1A—C6A	−3.0 (5)	C11B—C12B—C13B—C8B	−0.6 (5)
N1B—C1B—C2B—O1B	−177.3 (3)	C13C—C8C—C9C—C10C	0.0
C7B—C1B—C2B—O1B	1.1 (5)	O3C—C8C—C9C—C10C	−179.7 (7)
N1B—C1B—C2B—C3B	−0.8 (5)	C8C—C9C—C10C—C11C	0.0
C7B—C1B—C2B—C3B	177.5 (3)	C9C—C10C—C11C—C12C	0.0
O1B—C2B—C3B—O2B	0.7 (5)	C10C—C11C—C12C—C13C	0.0
C1B—C2B—C3B—O2B	−175.6 (3)	C11C—C12C—C13C—O4C	−179.1 (6)
O1B—C2B—C3B—C4B	−179.7 (3)	C11C—C12C—C13C—C8C	0.0
C1B—C2B—C3B—C4B	4.0 (5)	C9C—C8C—C13C—O4C	179.0 (7)
O2B—C3B—C4B—C5B	176.1 (3)	O3C—C8C—C13C—O4C	−1.3 (7)
C2B—C3B—C4B—C5B	−3.5 (5)	C9C—C8C—C13C—C12C	0.0
C3B—C4B—C5B—N1B	−0.2 (5)	O3C—C8C—C13C—C12C	179.7 (6)
C4B—C5B—N1B—C1B	3.7 (5)	C13'—C8'—C9'—O4'	178.4 (8)
C4B—C5B—N1B—C6B	−177.5 (3)	O3'—C8'—C9'—O4'	0.9 (9)
C2B—C1B—N1B—C5B	−3.1 (5)	C13'—C8'—C9'—C10'	0.0
C7B—C1B—N1B—C5B	178.5 (3)	O3'—C8'—C9'—C10'	−177.5 (8)
C2B—C1B—N1B—C6B	178.1 (3)	O4'—C9'—C10'—C11'	−178.5 (8)
C7B—C1B—N1B—C6B	−0.3 (5)	C8'—C9'—C10'—C11'	0.0
O3A—C8A—C9A—O4A	1.6 (5)	C9'—C10'—C11'—C12'	0.0
C13A—C8A—C9A—O4A	−178.4 (3)	C10'—C11'—C12'—C13'	0.0
O3A—C8A—C9A—C10A	179.9 (3)	C11'—C12'—C13'—C8'	0.0
C13A—C8A—C9A—C10A	0.0 (5)	C9'—C8'—C13'—C12'	0.0
O4A—C9A—C10A—C11A	179.0 (3)	O3'—C8'—C13'—C12'	177.3 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2B	0.84	1.95	2.702 (3)	148
O1B—H1B···O2A	0.84	1.81	2.617 (4)	161
O3A—H3A···O4A	0.84	2.28	2.726 (3)	113
O3A—H3A···O4B	0.84	2.06	2.833 (4)	153
O4A—H4A1···O2B^i	0.84	1.88	2.702 (3)	165
O3B—H3B···O4A	0.84	2.11	2.849 (4)	146
O3B—H3B···O4B	0.84	2.26	2.719 (4)	115
O4B—H4B1···O2B	0.84	1.85	2.686 (3)	175
O3C^a—H3C^a···O2A	0.84	2.11	2.684 (6)	125
O3′^b—H3′^b···O2A	0.84	1.81	2.646 (7)	174
O4′^b—H4′^b···O3′^b	0.84	2.30	2.715 (11)	111
C5A—H5A···O1A^i	0.95	2.42	3.164 (5)	135
C4B—H4B···O4A^ii	0.95	2.56	3.223 (4)	127
C5B—H5B···O1B^ii	0.95	2.43	3.159 (4)	133
C10C^a—H10C^a···O4C^a^i	0.95	2.37	3.112 (9)	134

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

(KA955_0m_def-cat_1_1_form1)

Crystal data

C7H9NO2·C6H6O2	Dx = 1.368 Mg m^−3
Mr = 249.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9084 reflections
a = 9.4231 (1) Å	θ = 2.7–30.5°
b = 10.3938 (1) Å	µ = 0.10 mm^−1
c = 24.7171 (3) Å	T = 100 K
V = 2420.84 (5) Å^3	Needle, colorless
Z = 8	0.32 × 0.16 × 0.14 mm
F(000) = 1056

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	2970 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.033
ω and φ scans	θmax = 30.6°, θmin = 2.7°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −10→13
Tmin = 0.695, Tmax = 0.746	k = −11→14
16449 measured reflections	l = −35→34
3709 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.042P)^2 + 1.3237P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3709 reflections	Δρmax = 0.44 e Å^−3
177 parameters	Δρmin = −0.26 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	0.66723 (13)	0.96080 (10)	0.55761 (4)	0.0126 (2)
C2	0.70159 (12)	0.94328 (10)	0.50386 (4)	0.0121 (2)
C3	0.62955 (13)	0.85230 (10)	0.47042 (4)	0.0117 (2)
C4	0.52122 (13)	0.78110 (10)	0.49606 (5)	0.0139 (2)
H4	0.469658	0.718666	0.476022	0.017*
C5	0.48954 (13)	0.80096 (10)	0.54951 (4)	0.0139 (2)
H5	0.415861	0.752016	0.565773	0.017*
C6	0.51967 (14)	0.90743 (12)	0.63704 (4)	0.0173 (2)
H6A	0.483873	0.995152	0.642042	0.026*
H6B	0.602676	0.894006	0.660251	0.026*
H6C	0.445398	0.845602	0.646743	0.026*
C7	0.74235 (15)	1.05827 (12)	0.59171 (5)	0.0195 (3)
H7A	0.819646	1.097080	0.570794	0.029*
H7B	0.781373	1.016220	0.623926	0.029*
H7C	0.675255	1.125362	0.602738	0.029*
N1	0.56054 (11)	0.88862 (9)	0.57980 (4)	0.0127 (2)
O1	0.80951 (10)	1.01425 (8)	0.48340 (3)	0.0184 (2)
H1O	0.8060 (19)	1.0123 (17)	0.4482 (7)	0.031 (5)*
C8	0.93540 (13)	1.08553 (10)	0.34185 (4)	0.0124 (2)
C9	0.94223 (13)	0.96060 (10)	0.32084 (4)	0.0132 (2)
C10	1.04269 (14)	0.93083 (12)	0.28180 (5)	0.0174 (2)
H10	1.048064	0.845799	0.267849	0.021*
C11	1.13542 (15)	1.02439 (13)	0.26296 (5)	0.0209 (3)
H11	1.204309	1.003196	0.236352	0.025*
C12	1.12751 (15)	1.14887 (13)	0.28299 (5)	0.0211 (3)
H12	1.190219	1.213222	0.269816	0.025*
C13	1.02741 (14)	1.17936 (11)	0.32246 (5)	0.0175 (2)
H13	1.022025	1.264603	0.336171	0.021*
O2	0.66500 (10)	0.83992 (7)	0.42014 (3)	0.01465 (18)
O3	0.83552 (10)	1.10809 (8)	0.38077 (3)	0.01516 (18)
H3O	0.843 (2)	1.189 (2)	0.3932 (8)	0.051 (6)*
O4	0.85051 (10)	0.86689 (8)	0.33754 (3)	0.01696 (19)
H4O	0.797 (2)	0.8911 (17)	0.3634 (7)	0.033 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0116 (6)	0.0116 (5)	0.0148 (5)	−0.0001 (4)	−0.0011 (4)	0.0009 (4)
C2	0.0106 (6)	0.0104 (4)	0.0154 (5)	−0.0012 (4)	−0.0009 (4)	0.0017 (3)
C3	0.0118 (6)	0.0085 (4)	0.0147 (5)	0.0023 (4)	−0.0011 (4)	0.0001 (3)
C4	0.0125 (6)	0.0114 (5)	0.0177 (5)	−0.0013 (4)	−0.0011 (4)	−0.0004 (4)
C5	0.0112 (6)	0.0113 (5)	0.0191 (5)	−0.0007 (4)	0.0010 (4)	0.0020 (4)
C6	0.0185 (6)	0.0196 (5)	0.0137 (5)	−0.0015 (5)	0.0039 (4)	0.0014 (4)
C7	0.0216 (7)	0.0217 (6)	0.0151 (5)	−0.0084 (5)	−0.0003 (5)	−0.0024 (4)
N1	0.0125 (5)	0.0119 (4)	0.0137 (4)	0.0008 (4)	0.0007 (4)	0.0022 (3)
O1	0.0192 (5)	0.0212 (4)	0.0147 (4)	−0.0103 (4)	0.0022 (3)	0.0000 (3)
C8	0.0126 (6)	0.0135 (5)	0.0112 (4)	0.0017 (4)	0.0000 (4)	0.0008 (4)
C9	0.0138 (6)	0.0133 (5)	0.0123 (4)	0.0006 (4)	−0.0022 (4)	0.0000 (4)
C10	0.0176 (7)	0.0206 (5)	0.0140 (5)	0.0044 (5)	−0.0014 (4)	−0.0042 (4)
C11	0.0171 (7)	0.0307 (7)	0.0149 (5)	0.0027 (5)	0.0034 (5)	0.0000 (4)
C12	0.0180 (7)	0.0250 (6)	0.0204 (5)	−0.0025 (5)	0.0023 (5)	0.0053 (4)
C13	0.0186 (7)	0.0148 (5)	0.0192 (5)	−0.0016 (5)	0.0015 (5)	0.0020 (4)
O2	0.0188 (5)	0.0115 (3)	0.0137 (4)	−0.0017 (3)	0.0014 (3)	−0.0012 (3)
O3	0.0191 (5)	0.0100 (4)	0.0164 (4)	0.0004 (3)	0.0056 (3)	−0.0015 (3)
O4	0.0206 (5)	0.0115 (4)	0.0188 (4)	−0.0015 (3)	0.0046 (3)	−0.0025 (3)

Geometric parameters (Å, º)

C1—N1	1.3691 (15)	C7—H7C	0.9800
C1—C2	1.3797 (15)	O1—H1O	0.870 (17)
C1—C7	1.4959 (16)	C8—O3	1.3660 (14)
C2—O1	1.3542 (14)	C8—C13	1.3902 (16)
C2—C3	1.4276 (15)	C8—C9	1.3999 (15)
C3—O2	1.2933 (13)	C9—O4	1.3660 (14)
C3—C4	1.4110 (16)	C9—C10	1.3868 (17)
C4—C5	1.3700 (16)	C10—C11	1.3878 (18)
C4—H4	0.9500	C10—H10	0.9500
C5—N1	1.3559 (14)	C11—C12	1.3873 (19)
C5—H5	0.9500	C11—H11	0.9500
C6—N1	1.4792 (14)	C12—C13	1.3935 (18)
C6—H6A	0.9800	C12—H12	0.9500
C6—H6B	0.9800	C13—H13	0.9500
C6—H6C	0.9800	O3—H3O	0.90 (2)
C7—H7A	0.9800	O4—H4O	0.851 (19)
C7—H7B	0.9800
N1—C1—C2	119.07 (10)	H7B—C7—H7C	109.5
N1—C1—C7	119.53 (10)	C5—N1—C1	120.62 (9)
C2—C1—C7	121.39 (10)	C5—N1—C6	119.25 (10)
O1—C2—C1	117.64 (10)	C1—N1—C6	120.13 (10)
O1—C2—C3	120.12 (10)	C2—O1—H1O	109.3 (12)
C1—C2—C3	122.23 (10)	O3—C8—C13	123.51 (10)
O2—C3—C4	124.49 (10)	O3—C8—C9	116.88 (10)
O2—C3—C2	119.96 (10)	C13—C8—C9	119.61 (11)
C4—C3—C2	115.56 (10)	O4—C9—C10	118.88 (10)
C5—C4—C3	120.77 (10)	O4—C9—C8	121.35 (10)
C5—C4—H4	119.6	C10—C9—C8	119.77 (11)
C3—C4—H4	119.6	C9—C10—C11	120.46 (11)
N1—C5—C4	121.75 (11)	C9—C10—H10	119.8
N1—C5—H5	119.1	C11—C10—H10	119.8
C4—C5—H5	119.1	C12—C11—C10	120.00 (12)
N1—C6—H6A	109.5	C12—C11—H11	120.0
N1—C6—H6B	109.5	C10—C11—H11	120.0
H6A—C6—H6B	109.5	C11—C12—C13	119.88 (12)
N1—C6—H6C	109.5	C11—C12—H12	120.1
H6A—C6—H6C	109.5	C13—C12—H12	120.1
H6B—C6—H6C	109.5	C8—C13—C12	120.27 (11)
C1—C7—H7A	109.5	C8—C13—H13	119.9
C1—C7—H7B	109.5	C12—C13—H13	119.9
H7A—C7—H7B	109.5	C8—O3—H3O	110.2 (13)
C1—C7—H7C	109.5	C9—O4—H4O	112.9 (12)
H7A—C7—H7C	109.5
N1—C1—C2—O1	−178.68 (10)	C7—C1—N1—C5	179.06 (11)
C7—C1—C2—O1	2.35 (16)	C2—C1—N1—C6	−178.75 (10)
N1—C1—C2—C3	0.04 (17)	C7—C1—N1—C6	0.24 (16)
C7—C1—C2—C3	−178.93 (11)	O3—C8—C9—O4	1.74 (16)
O1—C2—C3—O2	−1.74 (16)	C13—C8—C9—O4	−177.78 (10)
C1—C2—C3—O2	179.57 (10)	O3—C8—C9—C10	−179.04 (10)
O1—C2—C3—C4	178.45 (10)	C13—C8—C9—C10	1.44 (17)
C1—C2—C3—C4	−0.24 (16)	O4—C9—C10—C11	178.50 (11)
O2—C3—C4—C5	−179.45 (11)	C8—C9—C10—C11	−0.74 (18)
C2—C3—C4—C5	0.34 (16)	C9—C10—C11—C12	−0.35 (19)
C3—C4—C5—N1	−0.26 (18)	C10—C11—C12—C13	0.7 (2)
C4—C5—N1—C1	0.04 (17)	O3—C8—C13—C12	179.45 (11)
C4—C5—N1—C6	178.86 (11)	C9—C8—C13—C12	−1.06 (18)
C2—C1—N1—C5	0.07 (16)	C11—C12—C13—C8	−0.01 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3	0.870 (17)	1.963 (17)	2.7289 (11)	146.3 (16)
O3—H3O···O2^i	0.90 (2)	1.70 (2)	2.5987 (11)	172 (2)
O4—H4O···O2	0.851 (19)	1.950 (19)	2.7024 (12)	146.8 (17)
C5—H5···O2^ii	0.95	2.57	3.4726 (15)	158
C6—H6C···O4^ii	0.98	2.41	3.3264 (15)	155

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

(KA1027_0m_4def-cat_1_1_form2)

Crystal data

C7H9NO2·C6H6O2	F(000) = 528
Mr = 249.26	Dx = 1.374 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.867 (3) Å	Cell parameters from 6762 reflections
b = 9.550 (2) Å	θ = 2.7–30.7°
c = 10.487 (2) Å	µ = 0.10 mm^−1
β = 110.761 (7)°	T = 100 K
V = 1205.1 (5) Å^3	Block, colorless
Z = 4	0.26 × 0.24 × 0.18 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	2125 measured reflections
Radiation source: microfocus	2125 independent reflections
ω and φ scans	1755 reflections with I > 2σ(I)
Absorption correction: multi-scan SADABS, Bruker, 2016	Rint = 0.071
Tmin = 0.686, Tmax = 0.746	θmax = 25.0°, θmin = 2.7°

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.086	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.203	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 5.1435P] where P = (Fo^2 + 2Fc^2)/3
S = 1.25	(Δ/σ)max < 0.001
2125 reflections	Δρmax = 0.38 e Å^−3
177 parameters	Δρmin = −0.38 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	0.6092 (3)	0.1664 (4)	1.0866 (4)	0.0153 (9)
C2	0.4997 (3)	0.2036 (4)	1.0566 (4)	0.0146 (9)
C3	0.4313 (3)	0.1361 (4)	1.1195 (4)	0.0149 (9)
C4	0.4823 (3)	0.0299 (4)	1.2123 (4)	0.0172 (9)
H4	0.440667	−0.018518	1.257328	0.021*
C5	0.5908 (3)	−0.0053 (4)	1.2395 (4)	0.0160 (9)
H5	0.623165	−0.078582	1.302291	0.019*
C6	0.7707 (3)	0.0197 (5)	1.2108 (4)	0.0196 (10)
H6A	0.779711	−0.020463	1.129388	0.029*
H6B	0.790890	−0.050254	1.283867	0.029*
H6C	0.818976	0.101786	1.240608	0.029*
C7	0.6800 (4)	0.2378 (5)	1.0204 (5)	0.0259 (11)
H7A	0.635731	0.308211	0.955960	0.039*
H7B	0.707886	0.168534	0.971404	0.039*
H7C	0.742808	0.283428	1.090196	0.039*
O1	0.4587 (3)	0.3097 (3)	0.9670 (3)	0.0241 (8)
H1O	0.391 (7)	0.310 (8)	0.945 (8)	0.08 (3)*
O2	0.3284 (2)	0.1748 (3)	1.0879 (3)	0.0179 (7)
N1	0.6534 (3)	0.0623 (4)	1.1784 (3)	0.0160 (8)
C8	0.1729 (3)	0.4424 (4)	0.7692 (4)	0.0143 (9)
C9	0.1345 (3)	0.4598 (4)	0.8763 (4)	0.0155 (9)
C10	0.0592 (4)	0.5661 (5)	0.8703 (5)	0.0207 (10)
H10	0.033708	0.579797	0.943963	0.025*
C11	0.0218 (4)	0.6513 (5)	0.7578 (5)	0.0229 (10)
H11	−0.029763	0.723678	0.754502	0.027*
C12	0.0577 (4)	0.6336 (5)	0.6491 (5)	0.0241 (10)
H12	0.030612	0.692229	0.571093	0.029*
C13	0.1347 (4)	0.5276 (5)	0.6565 (4)	0.0214 (10)
H13	0.160714	0.514500	0.583096	0.026*
O3	0.2485 (2)	0.3362 (3)	0.7826 (3)	0.0172 (7)
H3O	0.268 (4)	0.343 (5)	0.704 (5)	0.017 (12)*
O4	0.1675 (3)	0.3741 (3)	0.9884 (3)	0.0216 (7)
H4O	0.211 (6)	0.305 (7)	0.975 (7)	0.06 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.016 (2)	0.014 (2)	0.011 (2)	−0.0016 (16)	−0.0002 (16)	0.0009 (16)
C2	0.014 (2)	0.014 (2)	0.012 (2)	−0.0004 (16)	0.0005 (16)	0.0005 (16)
C3	0.019 (2)	0.015 (2)	0.0070 (19)	0.0001 (16)	0.0000 (16)	−0.0030 (16)
C4	0.022 (2)	0.017 (2)	0.014 (2)	−0.0007 (17)	0.0073 (18)	0.0004 (16)
C5	0.023 (2)	0.014 (2)	0.0073 (19)	0.0030 (17)	0.0003 (17)	0.0020 (16)
C6	0.011 (2)	0.024 (2)	0.019 (2)	0.0043 (17)	−0.0002 (17)	0.0017 (18)
C7	0.016 (2)	0.026 (2)	0.030 (3)	0.0024 (19)	0.0015 (19)	0.013 (2)
O1	0.0136 (16)	0.0263 (18)	0.0299 (18)	0.0051 (13)	0.0045 (14)	0.0164 (14)
O2	0.0145 (15)	0.0213 (16)	0.0161 (15)	0.0038 (12)	0.0033 (12)	0.0035 (12)
N1	0.0134 (18)	0.0158 (18)	0.0147 (18)	0.0017 (14)	−0.0002 (14)	−0.0002 (14)
C8	0.0069 (19)	0.017 (2)	0.015 (2)	−0.0021 (15)	−0.0008 (16)	−0.0020 (16)
C9	0.014 (2)	0.015 (2)	0.013 (2)	−0.0053 (16)	−0.0004 (16)	−0.0028 (16)
C10	0.018 (2)	0.019 (2)	0.026 (2)	−0.0004 (17)	0.0094 (19)	−0.0025 (19)
C11	0.017 (2)	0.018 (2)	0.031 (3)	0.0035 (17)	0.0053 (19)	0.0012 (19)
C12	0.021 (2)	0.019 (2)	0.026 (2)	0.0024 (18)	0.0006 (19)	0.0070 (19)
C13	0.020 (2)	0.024 (2)	0.019 (2)	−0.0009 (18)	0.0048 (18)	0.0010 (18)
O3	0.0180 (15)	0.0191 (16)	0.0134 (15)	0.0055 (12)	0.0042 (12)	0.0022 (12)
O4	0.0244 (17)	0.0248 (17)	0.0153 (16)	0.0075 (14)	0.0064 (13)	0.0041 (13)

Geometric parameters (Å, º)

C1—N1	1.361 (5)	C7—H7C	0.9800
C1—C2	1.378 (6)	O1—H1O	0.82 (8)
C1—C7	1.491 (6)	C8—C13	1.375 (6)
C2—O1	1.355 (5)	C8—O3	1.377 (5)
C2—C3	1.427 (6)	C8—C9	1.388 (6)
C3—O2	1.299 (5)	C9—O4	1.370 (5)
C3—C4	1.398 (6)	C9—C10	1.389 (6)
C4—C5	1.365 (6)	C10—C11	1.372 (6)
C4—H4	0.9500	C10—H10	0.9500
C5—N1	1.357 (5)	C11—C12	1.384 (7)
C5—H5	0.9500	C11—H11	0.9500
C6—N1	1.481 (5)	C12—C13	1.399 (6)
C6—H6A	0.9800	C12—H12	0.9500
C6—H6B	0.9800	C13—H13	0.9500
C6—H6C	0.9800	O3—H3O	0.95 (5)
C7—H7A	0.9800	O4—H4O	0.91 (7)
C7—H7B	0.9800
N1—C1—C2	119.2 (4)	H7B—C7—H7C	109.5
N1—C1—C7	119.5 (4)	C2—O1—H1O	108 (6)
C2—C1—C7	121.3 (4)	C5—N1—C1	120.8 (3)
O1—C2—C1	117.8 (4)	C5—N1—C6	119.2 (3)
O1—C2—C3	120.4 (4)	C1—N1—C6	120.0 (4)
C1—C2—C3	121.8 (4)	C13—C8—O3	123.2 (4)
O2—C3—C4	124.6 (4)	C13—C8—C9	120.2 (4)
O2—C3—C2	119.6 (4)	O3—C8—C9	116.5 (4)
C4—C3—C2	115.8 (4)	O4—C9—C8	122.1 (4)
C5—C4—C3	121.1 (4)	O4—C9—C10	118.4 (4)
C5—C4—H4	119.4	C8—C9—C10	119.5 (4)
C3—C4—H4	119.4	C11—C10—C9	120.0 (4)
N1—C5—C4	121.3 (4)	C11—C10—H10	120.0
N1—C5—H5	119.4	C9—C10—H10	120.0
C4—C5—H5	119.4	C10—C11—C12	121.2 (4)
N1—C6—H6A	109.5	C10—C11—H11	119.4
N1—C6—H6B	109.5	C12—C11—H11	119.4
H6A—C6—H6B	109.5	C11—C12—C13	118.7 (4)
N1—C6—H6C	109.5	C11—C12—H12	120.7
H6A—C6—H6C	109.5	C13—C12—H12	120.7
H6B—C6—H6C	109.5	C8—C13—C12	120.4 (4)
C1—C7—H7A	109.5	C8—C13—H13	119.8
C1—C7—H7B	109.5	C12—C13—H13	119.8
H7A—C7—H7B	109.5	C8—O3—H3O	105 (3)
C1—C7—H7C	109.5	C9—O4—H4O	109 (4)
H7A—C7—H7C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2	0.82 (8)	2.33 (8)	2.754 (4)	113 (6)
O1—H1O···O3	0.82 (8)	2.03 (8)	2.723 (4)	142 (7)
O3—H3O···O2^i	0.95 (5)	1.67 (5)	2.594 (4)	165 (4)
O4—H4O···O2	0.91 (7)	1.99 (7)	2.732 (4)	138 (6)
O4—H4O···O3	0.91 (7)	2.26 (7)	2.733 (4)	112 (5)
C5—H5···O2^ii	0.95	2.60	3.516 (5)	162
C6—H6B···O4^ii	0.98	2.37	3.277 (5)	154

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+5/2.

(KA254_0M_def-hq_1_0.5)

Crystal data

C7H9NO2·0.5(C6H6O2)	Z = 2
Mr = 194.21	F(000) = 206
Triclinic, P1	Dx = 1.450 Mg m^−3
a = 6.83171 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.09634 (10) Å	Cell parameters from 8964 reflections
c = 10.01294 (14) Å	θ = 3.1–30.5°
α = 72.4243 (4)°	µ = 0.11 mm^−1
β = 85.7351 (4)°	T = 100 K
γ = 73.9285 (4)°	Block, colorless
V = 444.66 (1) Å^3	0.41 × 0.38 × 0.22 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	2471 reflections with I > 2σ(I)
ω and φ scans	Rint = 0.024
Absorption correction: multi-scan SADABS, Bruker,2016	θmax = 30.5°, θmin = 2.1°
Tmin = 0.719, Tmax = 0.746	h = −8→9
11173 measured reflections	k = −9→10
2708 independent reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.1917P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2708 reflections	Δρmax = 0.45 e Å^−3
137 parameters	Δρmin = −0.26 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	1.06764 (12)	0.64378 (13)	0.60013 (8)	0.00925 (16)
C2	0.86615 (13)	0.75480 (13)	0.57949 (8)	0.00904 (16)
C3	0.71807 (12)	0.73275 (13)	0.68833 (9)	0.00915 (16)
C4	0.79096 (13)	0.58247 (13)	0.81665 (9)	0.01072 (16)
H4	0.6997	0.5572	0.8922	0.013*
C5	0.99177 (13)	0.47335 (13)	0.83276 (9)	0.01053 (16)
H5	1.0366	0.3727	0.9195	0.013*
C6	1.34255 (13)	0.38421 (14)	0.75540 (10)	0.01397 (18)
H6A	1.3790	0.2921	0.6963	0.021*
H6B	1.3606	0.3031	0.8542	0.021*
H6C	1.4306	0.4774	0.7333	0.021*
C7	1.22236 (13)	0.66929 (14)	0.48694 (9)	0.01321 (17)
H7A	1.1544	0.7622	0.3994	0.020*
H7B	1.2910	0.5355	0.4736	0.020*
H7C	1.3229	0.7270	0.5137	0.020*
N1	1.12814 (11)	0.50447 (11)	0.72884 (8)	0.00952 (15)
O1	0.80721 (10)	0.88597 (10)	0.45067 (7)	0.01354 (15)
H1O	0.677 (3)	0.949 (3)	0.452 (2)	0.052 (6)*
O2	0.53234 (10)	0.84161 (10)	0.66573 (7)	0.01308 (15)
C8	0.20047 (12)	0.92636 (13)	0.95892 (8)	0.00975 (16)
C9	0.03678 (13)	0.95351 (13)	0.87318 (8)	0.01011 (16)
H9	0.0612	0.9223	0.7866	0.012*
C10	−0.16245 (13)	1.02634 (13)	0.91429 (9)	0.01028 (16)
H10	−0.2732	1.0439	0.8556	0.012*
O3	0.39904 (10)	0.85127 (11)	0.92593 (7)	0.01518 (15)
H2O	0.412 (3)	0.851 (3)	0.840 (2)	0.041 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0085 (3)	0.0101 (3)	0.0085 (3)	−0.0019 (3)	0.0000 (3)	−0.0023 (3)
C2	0.0091 (3)	0.0099 (3)	0.0071 (3)	−0.0017 (3)	−0.0001 (3)	−0.0017 (3)
C3	0.0080 (3)	0.0105 (3)	0.0086 (3)	−0.0018 (3)	0.0002 (3)	−0.0030 (3)
C4	0.0095 (4)	0.0124 (4)	0.0086 (3)	−0.0021 (3)	0.0011 (3)	−0.0016 (3)
C5	0.0109 (4)	0.0102 (3)	0.0085 (3)	−0.0017 (3)	0.0000 (3)	−0.0009 (3)
C6	0.0075 (4)	0.0154 (4)	0.0147 (4)	0.0010 (3)	−0.0016 (3)	−0.0015 (3)
C7	0.0094 (4)	0.0164 (4)	0.0116 (4)	−0.0024 (3)	0.0028 (3)	−0.0026 (3)
N1	0.0073 (3)	0.0101 (3)	0.0094 (3)	−0.0006 (2)	−0.0007 (2)	−0.0018 (2)
O1	0.0097 (3)	0.0168 (3)	0.0077 (3)	0.0014 (2)	−0.0002 (2)	0.0013 (2)
O2	0.0074 (3)	0.0167 (3)	0.0104 (3)	0.0012 (2)	−0.0004 (2)	−0.0011 (2)
C8	0.0077 (3)	0.0102 (3)	0.0091 (3)	−0.0008 (3)	0.0020 (3)	−0.0014 (3)
C9	0.0108 (4)	0.0109 (4)	0.0076 (3)	−0.0021 (3)	0.0011 (3)	−0.0021 (3)
C10	0.0092 (4)	0.0117 (4)	0.0085 (3)	−0.0018 (3)	−0.0002 (3)	−0.0018 (3)
O3	0.0075 (3)	0.0232 (3)	0.0116 (3)	0.0012 (2)	0.0023 (2)	−0.0057 (3)

Geometric parameters (Å, º)

C1—N1	1.3757 (10)	C6—H6C	0.9800
C1—C2	1.3790 (11)	C7—H7A	0.9800
C1—C7	1.4961 (12)	C7—H7B	0.9800
C2—O1	1.3554 (10)	C7—H7C	0.9800
C2—C3	1.4339 (11)	O1—H1O	0.88 (2)
C3—O2	1.2855 (10)	C8—O3	1.3685 (10)
C3—C4	1.4177 (11)	C8—C9	1.3959 (12)
C4—C5	1.3700 (11)	C8—C10^i	1.3971 (12)
C4—H4	0.9500	C9—C10	1.3946 (11)
C5—N1	1.3529 (11)	C9—H9	0.9500
C5—H5	0.9500	C10—C8^i	1.3970 (12)
C6—N1	1.4742 (11)	C10—H10	0.9500
C6—H6A	0.9800	O3—H2O	0.86 (2)
C6—H6B	0.9800
N1—C1—C2	118.91 (8)	C1—C7—H7A	109.5
N1—C1—C7	118.94 (7)	C1—C7—H7B	109.5
C2—C1—C7	122.15 (7)	H7A—C7—H7B	109.5
O1—C2—C1	118.26 (7)	C1—C7—H7C	109.5
O1—C2—C3	119.45 (7)	H7A—C7—H7C	109.5
C1—C2—C3	122.28 (8)	H7B—C7—H7C	109.5
O2—C3—C4	124.12 (8)	C5—N1—C1	120.70 (7)
O2—C3—C2	120.44 (8)	C5—N1—C6	118.77 (7)
C4—C3—C2	115.42 (7)	C1—N1—C6	120.53 (7)
C5—C4—C3	120.61 (8)	C2—O1—H1O	109.2 (13)
C5—C4—H4	119.7	O3—C8—C9	122.95 (8)
C3—C4—H4	119.7	O3—C8—C10^i	117.73 (8)
N1—C5—C4	122.01 (8)	C9—C8—C10^i	119.31 (7)
N1—C5—H5	119.0	C10—C9—C8	120.17 (7)
C4—C5—H5	119.0	C10—C9—H9	119.9
N1—C6—H6A	109.5	C8—C9—H9	119.9
N1—C6—H6B	109.5	C9—C10—C8^i	120.52 (8)
H6A—C6—H6B	109.5	C9—C10—H10	119.7
N1—C6—H6C	109.5	C8^i—C10—H10	119.7
H6A—C6—H6C	109.5	C8—O3—H2O	112.1 (12)
H6B—C6—H6C	109.5
N1—C1—C2—O1	−177.62 (7)	C3—C4—C5—N1	0.48 (14)
C7—C1—C2—O1	2.13 (13)	C4—C5—N1—C1	−2.23 (13)
N1—C1—C2—C3	1.13 (13)	C4—C5—N1—C6	178.60 (8)
C7—C1—C2—C3	−179.13 (8)	C2—C1—N1—C5	1.40 (12)
O1—C2—C3—O2	−2.48 (13)	C7—C1—N1—C5	−178.35 (8)
C1—C2—C3—O2	178.79 (8)	C2—C1—N1—C6	−179.45 (8)
O1—C2—C3—C4	176.02 (7)	C7—C1—N1—C6	0.80 (12)
C1—C2—C3—C4	−2.71 (12)	O3—C8—C9—C10	178.52 (8)
O2—C3—C4—C5	−179.66 (8)	C10^i—C8—C9—C10	−0.26 (14)
C2—C3—C4—C5	1.90 (12)	C8—C9—C10—C8^i	0.26 (14)

Symmetry code: (i) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^ii	0.88 (2)	1.91 (2)	2.6523 (9)	140.7 (18)
O3—H2O···O2	0.86 (2)	1.88 (2)	2.7097 (9)	160.6 (18)
C4—H4···O3	0.95	2.58	3.1625 (11)	120
C7—H7C···O2^iii	0.98	2.60	3.5361 (12)	161
C9—H9···O1^ii	0.95	2.59	3.2978 (10)	132

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

(KA951_0mdef-res_2_1)

Crystal data

2(C7H9NO2)·C6H6O2	F(000) = 824
Mr = 388.41	Dx = 1.385 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.71471 (15) Å	Cell parameters from 7177 reflections
b = 7.32566 (10) Å	θ = 2.6–30.5°
c = 22.0867 (3) Å	µ = 0.10 mm^−1
β = 100.6076 (7)°	T = 100 K
V = 1863.04 (4) Å^3	Block, colorless
Z = 4	0.36 × 0.28 × 0.18 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	4023 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.051
ω and φ scans	θmax = 30.5°, θmin = 2.2°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −15→16
Tmin = 0.570, Tmax = 0.746	k = −10→10
16659 measured reflections	l = −31→31
5665 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 1.3362P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5665 reflections	Δρmax = 0.35 e Å^−3
273 parameters	Δρmin = −0.40 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
C1A	0.00048 (13)	0.7409 (2)	0.79773 (7)	0.0136 (3)
C2A	0.02881 (12)	0.7559 (2)	0.74009 (7)	0.0125 (3)
C3A	0.13876 (13)	0.6954 (2)	0.72806 (7)	0.0126 (3)
C4A	0.21768 (13)	0.6298 (2)	0.77945 (7)	0.0149 (3)
H4A	0.292429	0.589378	0.774412	0.018*
C5A	0.18797 (13)	0.6235 (2)	0.83641 (7)	0.0162 (3)
H5A	0.242986	0.579842	0.870381	0.019*
C6A	0.05466 (15)	0.6591 (2)	0.90774 (7)	0.0196 (3)
H6A	0.000468	0.557440	0.908146	0.029*
H6B	0.018974	0.772256	0.918922	0.029*
H6C	0.126136	0.635299	0.937474	0.029*
C7A	−0.11812 (14)	0.7897 (2)	0.80881 (7)	0.0186 (3)
H7A	−0.169401	0.814112	0.769332	0.028*
H7B	−0.113139	0.898787	0.834833	0.028*
H7C	−0.149443	0.687982	0.829518	0.028*
N1A	0.08235 (11)	0.67786 (18)	0.84561 (6)	0.0138 (3)
O1A	−0.05101 (10)	0.82944 (17)	0.69425 (5)	0.0186 (3)
H1O	−0.039 (2)	0.801 (3)	0.6575 (12)	0.046 (7)*
O2A	0.16024 (9)	0.70137 (16)	0.67308 (5)	0.0153 (2)
C1B	0.10296 (13)	0.7833 (2)	0.46944 (7)	0.0132 (3)
C2B	0.05680 (13)	0.8045 (2)	0.52196 (7)	0.0118 (3)
C3B	−0.05645 (12)	0.7385 (2)	0.52614 (7)	0.0116 (3)
C4B	−0.11969 (13)	0.6579 (2)	0.47199 (7)	0.0130 (3)
H4B	−0.195888	0.612945	0.471623	0.016*
C5B	−0.07202 (13)	0.6442 (2)	0.42039 (7)	0.0138 (3)
H5B	−0.116342	0.590157	0.384528	0.017*
C6B	0.08152 (16)	0.6835 (2)	0.36112 (8)	0.0210 (4)
H6D	0.023032	0.623332	0.330086	0.032*
H6E	0.152148	0.608886	0.369076	0.032*
H6F	0.099681	0.803789	0.345985	0.032*
C7B	0.22516 (14)	0.8381 (2)	0.46654 (8)	0.0200 (3)
H7D	0.224097	0.937097	0.436599	0.030*
H7E	0.266981	0.733083	0.453876	0.030*
H7F	0.264275	0.879915	0.507242	0.030*
N1B	0.03605 (11)	0.70498 (18)	0.41845 (6)	0.0135 (3)
O1B	0.12117 (9)	0.89164 (16)	0.57104 (5)	0.0160 (2)
H2O	0.118 (2)	0.837 (3)	0.6070 (12)	0.044 (7)*
O2B	−0.09658 (9)	0.75194 (16)	0.57650 (5)	0.0148 (2)
C8	0.43028 (13)	0.6596 (2)	0.62482 (7)	0.0132 (3)
C9	0.49976 (13)	0.6426 (2)	0.58025 (7)	0.0140 (3)
H9	0.468191	0.593785	0.540871	0.017*
C10	0.61549 (13)	0.6972 (2)	0.59351 (7)	0.0132 (3)
C11	0.66151 (13)	0.7753 (2)	0.65022 (7)	0.0145 (3)
H11	0.740060	0.814780	0.659066	0.017*
C12	0.59007 (13)	0.7942 (2)	0.69370 (7)	0.0150 (3)
H12	0.620756	0.847754	0.732450	0.018*
C13	0.47511 (13)	0.7369 (2)	0.68191 (7)	0.0144 (3)
H13	0.427811	0.750170	0.712255	0.017*
O3	0.31994 (9)	0.59454 (17)	0.61019 (5)	0.0184 (3)
H3O	0.278 (2)	0.631 (4)	0.6371 (12)	0.049 (7)*
O4	0.68062 (10)	0.66889 (17)	0.54920 (5)	0.0192 (3)
H4O	0.754 (2)	0.702 (3)	0.5626 (10)	0.030 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0123 (7)	0.0151 (7)	0.0130 (7)	0.0002 (6)	0.0012 (5)	−0.0021 (6)
C2A	0.0099 (7)	0.0144 (7)	0.0125 (7)	0.0011 (5)	0.0003 (5)	−0.0015 (5)
C3A	0.0114 (7)	0.0117 (7)	0.0146 (7)	−0.0019 (5)	0.0020 (5)	−0.0009 (5)
C4A	0.0101 (7)	0.0160 (7)	0.0183 (8)	0.0013 (6)	0.0014 (5)	0.0015 (6)
C5A	0.0148 (7)	0.0152 (7)	0.0167 (7)	0.0007 (6)	−0.0022 (6)	0.0027 (6)
C6A	0.0268 (9)	0.0219 (8)	0.0106 (7)	0.0001 (7)	0.0049 (6)	0.0016 (6)
C7A	0.0156 (7)	0.0270 (9)	0.0140 (7)	0.0018 (7)	0.0050 (6)	−0.0032 (6)
N1A	0.0151 (6)	0.0150 (6)	0.0110 (6)	−0.0012 (5)	0.0019 (5)	0.0005 (5)
O1A	0.0138 (5)	0.0311 (7)	0.0103 (5)	0.0092 (5)	0.0006 (4)	−0.0012 (5)
O2A	0.0128 (5)	0.0211 (6)	0.0126 (5)	0.0013 (4)	0.0045 (4)	−0.0001 (4)
C1B	0.0118 (7)	0.0124 (7)	0.0158 (7)	−0.0003 (5)	0.0037 (5)	0.0028 (6)
C2B	0.0118 (7)	0.0103 (7)	0.0129 (7)	−0.0002 (5)	0.0011 (5)	0.0000 (5)
C3B	0.0102 (6)	0.0120 (7)	0.0128 (7)	0.0021 (5)	0.0024 (5)	0.0011 (5)
C4B	0.0113 (7)	0.0136 (7)	0.0140 (7)	−0.0014 (5)	0.0024 (5)	−0.0002 (6)
C5B	0.0145 (7)	0.0137 (7)	0.0132 (7)	−0.0007 (6)	0.0024 (5)	−0.0005 (6)
C6B	0.0253 (9)	0.0252 (9)	0.0158 (8)	−0.0027 (7)	0.0123 (6)	−0.0024 (6)
C7B	0.0138 (7)	0.0244 (9)	0.0235 (8)	−0.0026 (6)	0.0081 (6)	0.0023 (7)
N1B	0.0156 (6)	0.0136 (6)	0.0130 (6)	−0.0004 (5)	0.0069 (5)	−0.0004 (5)
O1B	0.0153 (5)	0.0186 (6)	0.0128 (5)	−0.0054 (4)	−0.0005 (4)	−0.0003 (4)
O2B	0.0128 (5)	0.0226 (6)	0.0097 (5)	0.0000 (4)	0.0035 (4)	−0.0014 (4)
C8	0.0095 (7)	0.0135 (7)	0.0171 (7)	−0.0002 (5)	0.0033 (5)	−0.0004 (6)
C9	0.0125 (7)	0.0168 (7)	0.0126 (7)	0.0003 (6)	0.0023 (5)	−0.0023 (6)
C10	0.0132 (7)	0.0159 (7)	0.0119 (7)	0.0009 (6)	0.0059 (5)	0.0008 (6)
C11	0.0104 (7)	0.0178 (8)	0.0156 (7)	−0.0019 (6)	0.0035 (5)	−0.0001 (6)
C12	0.0140 (7)	0.0190 (8)	0.0120 (7)	−0.0015 (6)	0.0026 (5)	−0.0031 (6)
C13	0.0133 (7)	0.0179 (8)	0.0135 (7)	−0.0003 (6)	0.0066 (5)	−0.0019 (6)
O3	0.0089 (5)	0.0253 (6)	0.0221 (6)	−0.0032 (5)	0.0059 (4)	−0.0083 (5)
O4	0.0110 (5)	0.0328 (7)	0.0156 (5)	−0.0026 (5)	0.0072 (4)	−0.0048 (5)

Geometric parameters (Å, º)

C1A—N1A	1.3705 (19)	C4B—C5B	1.362 (2)
C1A—C2A	1.378 (2)	C4B—H4B	0.9500
C1A—C7A	1.498 (2)	C5B—N1B	1.3500 (19)
C2A—O1A	1.3570 (18)	C5B—H5B	0.9500
C2A—C3A	1.433 (2)	C6B—N1B	1.4697 (19)
C3A—O2A	1.2852 (18)	C6B—H6D	0.9800
C3A—C4A	1.410 (2)	C6B—H6E	0.9800
C4A—C5A	1.367 (2)	C6B—H6F	0.9800
C4A—H4A	0.9500	C7B—H7D	0.9800
C5A—N1A	1.350 (2)	C7B—H7E	0.9800
C5A—H5A	0.9500	C7B—H7F	0.9800
C6A—N1A	1.4734 (19)	O1B—H2O	0.90 (2)
C6A—H6A	0.9800	C8—O3	1.3596 (18)
C6A—H6B	0.9800	C8—C9	1.394 (2)
C6A—H6C	0.9800	C8—C13	1.394 (2)
C7A—H7A	0.9800	C9—C10	1.392 (2)
C7A—H7B	0.9800	C9—H9	0.9500
C7A—H7C	0.9800	C10—O4	1.3630 (17)
O1A—H1O	0.87 (3)	C10—C11	1.392 (2)
C1B—N1B	1.374 (2)	C11—C12	1.392 (2)
C1B—C2B	1.376 (2)	C11—H11	0.9500
C1B—C7B	1.499 (2)	C12—C13	1.389 (2)
C2B—O1B	1.3603 (18)	C12—H12	0.9500
C2B—C3B	1.431 (2)	C13—H13	0.9500
C3B—O2B	1.2886 (17)	O3—H3O	0.88 (3)
C3B—C4B	1.415 (2)	O4—H4O	0.89 (2)
N1A—C1A—C2A	119.10 (13)	C5B—C4B—H4B	119.8
N1A—C1A—C7A	119.53 (13)	C3B—C4B—H4B	119.8
C2A—C1A—C7A	121.37 (14)	N1B—C5B—C4B	122.25 (14)
O1A—C2A—C1A	118.08 (13)	N1B—C5B—H5B	118.9
O1A—C2A—C3A	120.27 (13)	C4B—C5B—H5B	118.9
C1A—C2A—C3A	121.64 (14)	N1B—C6B—H6D	109.5
O2A—C3A—C4A	123.97 (14)	N1B—C6B—H6E	109.5
O2A—C3A—C2A	120.25 (13)	H6D—C6B—H6E	109.5
C4A—C3A—C2A	115.77 (13)	N1B—C6B—H6F	109.5
C5A—C4A—C3A	120.82 (14)	H6D—C6B—H6F	109.5
C5A—C4A—H4A	119.6	H6E—C6B—H6F	109.5
C3A—C4A—H4A	119.6	C1B—C7B—H7D	109.5
N1A—C5A—C4A	121.63 (14)	C1B—C7B—H7E	109.5
N1A—C5A—H5A	119.2	H7D—C7B—H7E	109.5
C4A—C5A—H5A	119.2	C1B—C7B—H7F	109.5
N1A—C6A—H6A	109.5	H7D—C7B—H7F	109.5
N1A—C6A—H6B	109.5	H7E—C7B—H7F	109.5
H6A—C6A—H6B	109.5	C5B—N1B—C1B	120.57 (13)
N1A—C6A—H6C	109.5	C5B—N1B—C6B	118.85 (13)
H6A—C6A—H6C	109.5	C1B—N1B—C6B	120.57 (13)
H6B—C6A—H6C	109.5	C2B—O1B—H2O	112.9 (16)
C1A—C7A—H7A	109.5	O3—C8—C9	117.01 (14)
C1A—C7A—H7B	109.5	O3—C8—C13	122.74 (13)
H7A—C7A—H7B	109.5	C9—C8—C13	120.24 (14)
C1A—C7A—H7C	109.5	C10—C9—C8	119.90 (14)
H7A—C7A—H7C	109.5	C10—C9—H9	120.0
H7B—C7A—H7C	109.5	C8—C9—H9	120.0
C5A—N1A—C1A	120.92 (13)	O4—C10—C9	117.22 (13)
C5A—N1A—C6A	118.53 (13)	O4—C10—C11	122.23 (14)
C1A—N1A—C6A	120.48 (13)	C9—C10—C11	120.55 (13)
C2A—O1A—H1O	113.2 (16)	C12—C11—C10	118.63 (14)
N1B—C1B—C2B	119.00 (13)	C12—C11—H11	120.7
N1B—C1B—C7B	118.82 (13)	C10—C11—H11	120.7
C2B—C1B—C7B	122.16 (14)	C13—C12—C11	121.73 (14)
O1B—C2B—C1B	118.59 (13)	C13—C12—H12	119.1
O1B—C2B—C3B	119.45 (13)	C11—C12—H12	119.1
C1B—C2B—C3B	121.96 (14)	C12—C13—C8	118.91 (13)
O2B—C3B—C4B	122.97 (13)	C12—C13—H13	120.5
O2B—C3B—C2B	121.32 (13)	C8—C13—H13	120.5
C4B—C3B—C2B	115.71 (13)	C8—O3—H3O	111.2 (17)
C5B—C4B—C3B	120.43 (14)	C10—O4—H4O	110.7 (13)
N1A—C1A—C2A—O1A	−175.89 (14)	C1B—C2B—C3B—O2B	176.85 (14)
C7A—C1A—C2A—O1A	5.0 (2)	O1B—C2B—C3B—C4B	176.90 (13)
N1A—C1A—C2A—C3A	4.4 (2)	C1B—C2B—C3B—C4B	−2.8 (2)
C7A—C1A—C2A—C3A	−174.76 (15)	O2B—C3B—C4B—C5B	−178.76 (14)
O1A—C2A—C3A—O2A	−3.7 (2)	C2B—C3B—C4B—C5B	0.9 (2)
C1A—C2A—C3A—O2A	176.01 (14)	C3B—C4B—C5B—N1B	0.3 (2)
O1A—C2A—C3A—C4A	176.86 (14)	C4B—C5B—N1B—C1B	0.3 (2)
C1A—C2A—C3A—C4A	−3.4 (2)	C4B—C5B—N1B—C6B	179.39 (15)
O2A—C3A—C4A—C5A	−178.50 (15)	C2B—C1B—N1B—C5B	−2.1 (2)
C2A—C3A—C4A—C5A	0.9 (2)	C7B—C1B—N1B—C5B	176.18 (14)
C3A—C4A—C5A—N1A	0.6 (2)	C2B—C1B—N1B—C6B	178.76 (14)
C4A—C5A—N1A—C1A	0.3 (2)	C7B—C1B—N1B—C6B	−2.9 (2)
C4A—C5A—N1A—C6A	177.19 (15)	O3—C8—C9—C10	−176.45 (14)
C2A—C1A—N1A—C5A	−2.8 (2)	C13—C8—C9—C10	2.2 (2)
C7A—C1A—N1A—C5A	176.39 (15)	C8—C9—C10—O4	176.84 (14)
C2A—C1A—N1A—C6A	−179.61 (14)	C8—C9—C10—C11	−2.4 (2)
C7A—C1A—N1A—C6A	−0.5 (2)	O4—C10—C11—C12	−178.02 (15)
N1B—C1B—C2B—O1B	−176.25 (13)	C9—C10—C11—C12	1.2 (2)
C7B—C1B—C2B—O1B	5.5 (2)	C10—C11—C12—C13	0.2 (2)
N1B—C1B—C2B—C3B	3.5 (2)	C11—C12—C13—C8	−0.4 (2)
C7B—C1B—C2B—C3B	−174.80 (14)	O3—C8—C13—C12	177.80 (15)
O1B—C2B—C3B—O2B	−3.5 (2)	C9—C8—C13—C12	−0.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O···O2B	0.87 (3)	1.83 (3)	2.6191 (15)	150 (2)
O1B—H2O···O2A	0.90 (2)	1.76 (3)	2.6177 (16)	160 (2)
O3—H3O···O2A	0.88 (3)	1.79 (3)	2.6457 (15)	164 (2)
O4—H4O···O2B^i	0.89 (2)	1.76 (2)	2.6394 (16)	170 (2)
C5A—H5A···O1B^ii	0.95	2.31	3.2218 (19)	160
C4B—H4B···O3^iii	0.95	2.59	3.2632 (19)	128
C4B—H4B···O4^iv	0.95	2.47	3.1393 (18)	127
C5B—H5B···O2A^iii	0.95	2.49	3.3098 (19)	144
C11—H11···O1A^i	0.95	2.43	3.3524 (19)	164

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

(KA1018_0m_def-res_1_1)

Crystal data

C7H9NO2·C6H6O2	F(000) = 528
Mr = 249.26	Dx = 1.398 Mg m^−3 Dm = colorless Mg m^−3 Dm measured by ?
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.13393 (8) Å	Cell parameters from 9916 reflections
b = 18.2199 (2) Å	θ = 2.2–30.6°
c = 9.1517 (1) Å	µ = 0.10 mm^−1
β = 95.4213 (4)°	T = 100 K
V = 1184.21 (2) Å^3	Block
Z = 4	0.28 × 0.24 × 0.17 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	2528 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.022
ω and φ scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −9→9
Tmin = 0.686, Tmax = 0.746	k = −20→23
12941 measured reflections	l = −11→11
2715 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)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0591P)^2 + 0.4132P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.105	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.38 e Å^−3
2715 reflections	Δρmin = −0.20 e Å^−3
178 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.026 (5)

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	0.34797 (14)	0.42574 (6)	0.36771 (11)	0.0132 (2)
C2	0.40005 (14)	0.46620 (5)	0.25087 (11)	0.0124 (2)
C3	0.26616 (14)	0.50666 (5)	0.15610 (11)	0.0121 (2)
C4	0.07844 (14)	0.50428 (6)	0.19399 (11)	0.0143 (2)
H4	−0.016728	0.530970	0.136996	0.017*
C5	0.03237 (14)	0.46415 (6)	0.31138 (11)	0.0149 (2)
H5	−0.095060	0.463082	0.333482	0.018*
C6	0.10146 (16)	0.37912 (6)	0.51535 (12)	0.0179 (2)
H6A	−0.031352	0.388862	0.527197	0.027*
H6B	0.177913	0.390082	0.607417	0.027*
H6C	0.117091	0.327365	0.489976	0.027*
C7	0.48703 (15)	0.38159 (6)	0.46339 (12)	0.0182 (2)
H7A	0.506876	0.404483	0.560518	0.027*
H7B	0.606772	0.379661	0.419124	0.027*
H7C	0.438629	0.331674	0.473263	0.027*
O1	0.58549 (10)	0.46813 (5)	0.22767 (9)	0.0177 (2)
H1O	0.598 (3)	0.4771 (10)	0.137 (2)	0.041 (5)*
O2	0.31733 (10)	0.54248 (4)	0.04550 (8)	0.01461 (19)
N1	0.16275 (12)	0.42583 (5)	0.39720 (9)	0.0132 (2)
C8	0.52644 (14)	0.69772 (6)	0.17439 (11)	0.0134 (2)
C9	0.34253 (14)	0.70504 (6)	0.21173 (11)	0.0131 (2)
H9	0.246363	0.673007	0.170895	0.016*
C10	0.30140 (14)	0.76005 (6)	0.30990 (11)	0.0134 (2)
C11	0.44171 (15)	0.80734 (6)	0.36981 (11)	0.0156 (2)
H11	0.413759	0.844168	0.437960	0.019*
C12	0.62358 (15)	0.79981 (6)	0.32826 (12)	0.0171 (2)
H12	0.719158	0.832580	0.367217	0.021*
C13	0.66813 (15)	0.74534 (6)	0.23098 (11)	0.0160 (2)
H13	0.792730	0.740654	0.203580	0.019*
O3	0.57473 (11)	0.64441 (4)	0.07833 (8)	0.01707 (19)
H3O	0.481 (3)	0.6080 (10)	0.070 (2)	0.043 (5)*
O4	0.11893 (11)	0.76519 (4)	0.34212 (9)	0.0182 (2)
H4O	0.111 (3)	0.8001 (10)	0.410 (2)	0.043 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0143 (5)	0.0126 (5)	0.0125 (5)	0.0004 (4)	0.0003 (4)	−0.0019 (4)
C2	0.0113 (5)	0.0131 (5)	0.0126 (5)	0.0001 (3)	0.0003 (4)	−0.0018 (4)
C3	0.0143 (5)	0.0099 (5)	0.0119 (4)	−0.0006 (3)	0.0002 (4)	−0.0017 (3)
C4	0.0136 (5)	0.0135 (5)	0.0155 (5)	0.0024 (4)	−0.0008 (4)	−0.0009 (4)
C5	0.0131 (5)	0.0146 (5)	0.0172 (5)	0.0006 (4)	0.0021 (4)	−0.0021 (4)
C6	0.0216 (5)	0.0165 (5)	0.0167 (5)	−0.0011 (4)	0.0066 (4)	0.0025 (4)
C7	0.0182 (5)	0.0196 (5)	0.0163 (5)	0.0025 (4)	−0.0006 (4)	0.0046 (4)
O1	0.0109 (4)	0.0276 (5)	0.0145 (4)	0.0017 (3)	0.0014 (3)	0.0051 (3)
O2	0.0168 (4)	0.0141 (4)	0.0129 (4)	−0.0004 (3)	0.0014 (3)	0.0015 (3)
N1	0.0150 (4)	0.0121 (4)	0.0128 (4)	−0.0009 (3)	0.0026 (3)	−0.0003 (3)
C8	0.0161 (5)	0.0127 (5)	0.0115 (5)	0.0004 (4)	0.0015 (4)	0.0029 (3)
C9	0.0137 (5)	0.0134 (5)	0.0120 (4)	−0.0022 (4)	−0.0006 (4)	0.0015 (4)
C10	0.0138 (5)	0.0143 (5)	0.0121 (5)	0.0008 (4)	0.0010 (4)	0.0037 (4)
C11	0.0202 (5)	0.0130 (5)	0.0134 (5)	−0.0007 (4)	0.0001 (4)	0.0003 (4)
C12	0.0181 (5)	0.0165 (5)	0.0159 (5)	−0.0053 (4)	−0.0026 (4)	0.0021 (4)
C13	0.0131 (5)	0.0181 (5)	0.0166 (5)	−0.0019 (4)	0.0009 (4)	0.0039 (4)
O3	0.0179 (4)	0.0149 (4)	0.0194 (4)	−0.0019 (3)	0.0066 (3)	−0.0018 (3)
O4	0.0146 (4)	0.0212 (4)	0.0195 (4)	0.0003 (3)	0.0047 (3)	−0.0037 (3)

Geometric parameters (Å, º)

C1—N1	1.3734 (13)	C7—H7C	0.9800
C1—C2	1.3783 (14)	O1—H1O	0.85 (2)
C1—C7	1.4946 (14)	C8—O3	1.3756 (12)
C2—O1	1.3600 (12)	C8—C9	1.3931 (14)
C2—C3	1.4323 (14)	C8—C13	1.3942 (15)
C3—O2	1.2859 (12)	C9—C10	1.3956 (14)
C3—C4	1.4153 (14)	C9—H9	0.9500
C4—C5	1.3652 (15)	C10—O4	1.3648 (12)
C4—H4	0.9500	C10—C11	1.3933 (15)
C5—N1	1.3533 (14)	C11—C12	1.3928 (15)
C5—H5	0.9500	C11—H11	0.9500
C6—N1	1.4744 (13)	C12—C13	1.3899 (15)
C6—H6A	0.9800	C12—H12	0.9500
C6—H6B	0.9800	C13—H13	0.9500
C6—H6C	0.9800	O3—H3O	0.937 (19)
C7—H7A	0.9800	O4—H4O	0.893 (19)
C7—H7B	0.9800
N1—C1—C2	119.12 (9)	H7B—C7—H7C	109.5
N1—C1—C7	118.89 (9)	C2—O1—H1O	110.2 (13)
C2—C1—C7	121.99 (9)	C5—N1—C1	120.52 (9)
O1—C2—C1	118.19 (9)	C5—N1—C6	119.23 (9)
O1—C2—C3	119.68 (9)	C1—N1—C6	120.06 (8)
C1—C2—C3	122.13 (9)	O3—C8—C9	121.53 (9)
O2—C3—C4	123.64 (9)	O3—C8—C13	117.41 (9)
O2—C3—C2	121.01 (9)	C9—C8—C13	121.06 (10)
C4—C3—C2	115.35 (9)	C8—C9—C10	119.13 (9)
C5—C4—C3	120.86 (9)	C8—C9—H9	120.4
C5—C4—H4	119.6	C10—C9—H9	120.4
C3—C4—H4	119.6	O4—C10—C11	122.48 (9)
N1—C5—C4	121.99 (9)	O4—C10—C9	116.82 (9)
N1—C5—H5	119.0	C11—C10—C9	120.70 (10)
C4—C5—H5	119.0	C12—C11—C10	119.00 (10)
N1—C6—H6A	109.5	C12—C11—H11	120.5
N1—C6—H6B	109.5	C10—C11—H11	120.5
H6A—C6—H6B	109.5	C13—C12—C11	121.36 (10)
N1—C6—H6C	109.5	C13—C12—H12	119.3
H6A—C6—H6C	109.5	C11—C12—H12	119.3
H6B—C6—H6C	109.5	C12—C13—C8	118.73 (10)
C1—C7—H7A	109.5	C12—C13—H13	120.6
C1—C7—H7B	109.5	C8—C13—H13	120.6
H7A—C7—H7B	109.5	C8—O3—H3O	109.4 (11)
C1—C7—H7C	109.5	C10—O4—H4O	109.0 (12)
H7A—C7—H7C	109.5
N1—C1—C2—O1	176.99 (9)	C7—C1—N1—C5	−178.85 (9)
C7—C1—C2—O1	−3.10 (15)	C2—C1—N1—C6	175.92 (9)
N1—C1—C2—C3	−1.98 (15)	C7—C1—N1—C6	−4.00 (14)
C7—C1—C2—C3	177.93 (9)	O3—C8—C9—C10	179.92 (9)
O1—C2—C3—O2	2.86 (15)	C13—C8—C9—C10	−1.40 (15)
C1—C2—C3—O2	−178.18 (9)	C8—C9—C10—O4	179.60 (9)
O1—C2—C3—C4	−176.77 (9)	C8—C9—C10—C11	0.19 (15)
C1—C2—C3—C4	2.19 (14)	O4—C10—C11—C12	−178.23 (9)
O2—C3—C4—C5	178.83 (10)	C9—C10—C11—C12	1.14 (15)
C2—C3—C4—C5	−1.56 (14)	C10—C11—C12—C13	−1.31 (15)
C3—C4—C5—N1	0.78 (16)	C11—C12—C13—C8	0.14 (15)
C4—C5—N1—C1	−0.48 (15)	O3—C8—C13—C12	179.97 (9)
C4—C5—N1—C6	−175.38 (9)	C9—C8—C13—C12	1.24 (15)
C2—C1—N1—C5	1.07 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.85 (2)	1.87 (2)	2.6638 (11)	154 (2)
O3—H3O···O2	0.937 (19)	1.673 (19)	2.6090 (11)	177 (2)
O4—H4O···O3^ii	0.893 (19)	1.88 (2)	2.7594 (11)	167 (2)
C5—H5···O1^iii	0.95	2.39	3.2084 (13)	144
C13—H13···O4^iv	0.95	2.58	3.2999 (13)	133

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

(KA773_0m_def-phg_2_1)

Crystal data

2(C7H9NO2)·C6H6O3	Dx = 1.441 Mg m^−3
Mr = 404.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4198 reflections
a = 6.9983 (2) Å	θ = 2.3–30.3°
b = 18.4416 (6) Å	µ = 0.11 mm^−1
c = 28.8960 (8) Å	T = 100 K
V = 3729.31 (19) Å^3	Block, colorless
Z = 8	0.28 × 0.24 × 0.12 mm
F(000) = 1712

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	2498 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.106
ω and φ scans	θmax = 26.3°, θmin = 2.6°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −6→8
Tmin = 0.656, Tmax = 0.746	k = −21→22
18441 measured reflections	l = −35→35
3759 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0352P)^2 + 3.1236P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3759 reflections	Δρmax = 0.27 e Å^−3
286 parameters	Δρmin = −0.30 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
C1A	1.0878 (4)	0.94502 (14)	0.54403 (8)	0.0124 (6)
C2A	0.9194 (4)	0.93700 (13)	0.56781 (7)	0.0105 (6)
C3A	0.7833 (4)	0.88173 (14)	0.55713 (7)	0.0114 (6)
C4A	0.8308 (4)	0.83800 (14)	0.51865 (8)	0.0140 (6)
H4A	0.746161	0.800564	0.509190	0.017*
C5A	0.9964 (4)	0.84889 (14)	0.49502 (8)	0.0155 (6)
H5A	1.024005	0.818670	0.469244	0.019*
C6A	1.3027 (4)	0.90659 (15)	0.48078 (8)	0.0186 (6)
H6A	1.409387	0.892534	0.500833	0.028*
H6B	1.320344	0.956772	0.470478	0.028*
H6C	1.298486	0.874442	0.453796	0.028*
C7A	1.2351 (4)	0.99952 (14)	0.55728 (8)	0.0166 (6)
H7A	1.185485	1.030147	0.582258	0.025*
H7B	1.265969	1.029772	0.530420	0.025*
H7C	1.350594	0.974499	0.567874	0.025*
O1A	0.8851 (3)	0.98286 (9)	0.60349 (6)	0.0144 (4)
H1O	0.766 (5)	0.9750 (16)	0.6178 (9)	0.031 (9)*
O2A	0.6314 (2)	0.87464 (9)	0.58151 (5)	0.0145 (4)
N1A	1.1224 (3)	0.90061 (11)	0.50665 (6)	0.0129 (5)
C1B	0.6777 (4)	0.85960 (13)	0.75243 (8)	0.0119 (6)
C2B	0.6565 (3)	0.88916 (14)	0.70906 (8)	0.0109 (6)
C3B	0.6000 (4)	0.96222 (13)	0.70218 (8)	0.0110 (6)
C4B	0.5589 (3)	1.00161 (14)	0.74259 (8)	0.0116 (5)
H4B	0.516178	1.050365	0.740205	0.014*
C5B	0.5795 (4)	0.97086 (14)	0.78508 (8)	0.0125 (6)
H5B	0.549349	0.998507	0.811841	0.015*
C6B	0.6726 (4)	0.87373 (15)	0.83712 (8)	0.0167 (6)
H6D	0.576882	0.836388	0.843823	0.025*
H6E	0.660788	0.913218	0.859635	0.025*
H6F	0.800729	0.852548	0.839157	0.025*
C7B	0.7337 (4)	0.78253 (14)	0.76013 (8)	0.0163 (6)
H7D	0.634968	0.758113	0.778441	0.024*
H7E	0.855593	0.780788	0.776789	0.024*
H7F	0.747372	0.758041	0.730211	0.024*
O1B	0.6944 (3)	0.84620 (10)	0.67188 (6)	0.0154 (4)
H2O	0.668 (4)	0.8684 (17)	0.6466 (10)	0.036 (10)*
O2B	0.5862 (2)	0.98766 (9)	0.66070 (5)	0.0131 (4)
N1B	0.6416 (3)	0.90233 (11)	0.79018 (6)	0.0122 (5)
C8	0.4243 (4)	0.65664 (14)	0.65454 (8)	0.0113 (5)
C9	0.2434 (4)	0.62709 (14)	0.66009 (7)	0.0117 (5)
H9	0.221819	0.589960	0.682274	0.014*
C10	0.0945 (4)	0.65236 (13)	0.63289 (8)	0.0107 (5)
C11	0.1226 (4)	0.70806 (13)	0.60133 (8)	0.0115 (6)
H11	0.019877	0.725611	0.583000	0.014*
C12	0.3043 (4)	0.73755 (13)	0.59715 (8)	0.0107 (6)
C13	0.4575 (4)	0.71206 (14)	0.62323 (7)	0.0109 (6)
H13	0.581578	0.732169	0.619639	0.013*
O3	0.5680 (3)	0.63034 (10)	0.68217 (6)	0.0160 (4)
H3O	0.686 (5)	0.6420 (18)	0.6707 (10)	0.044 (10)*
O4	−0.0849 (3)	0.62285 (11)	0.63639 (6)	0.0161 (4)
H4O	−0.080 (5)	0.5765 (18)	0.6457 (10)	0.044 (10)*
O5	0.3282 (3)	0.79285 (10)	0.56613 (6)	0.0153 (4)
H5O	0.447 (5)	0.8191 (19)	0.5724 (11)	0.061 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0123 (14)	0.0138 (14)	0.0112 (12)	0.0037 (12)	−0.0017 (11)	0.0029 (10)
C2A	0.0132 (15)	0.0112 (14)	0.0070 (11)	0.0018 (11)	−0.0022 (10)	0.0017 (10)
C3A	0.0139 (15)	0.0099 (14)	0.0104 (11)	0.0012 (11)	−0.0025 (10)	0.0041 (10)
C4A	0.0165 (16)	0.0114 (14)	0.0139 (12)	−0.0019 (12)	−0.0054 (11)	0.0015 (10)
C5A	0.0207 (15)	0.0167 (15)	0.0091 (11)	0.0044 (13)	0.0004 (11)	−0.0012 (11)
C6A	0.0156 (15)	0.0256 (16)	0.0147 (13)	0.0030 (13)	0.0060 (11)	0.0027 (11)
C7A	0.0151 (15)	0.0175 (15)	0.0172 (13)	−0.0015 (12)	0.0022 (11)	0.0031 (11)
O1A	0.0136 (11)	0.0148 (10)	0.0149 (9)	−0.0027 (8)	0.0041 (8)	−0.0046 (7)
O2A	0.0122 (10)	0.0177 (10)	0.0137 (8)	−0.0046 (8)	0.0013 (7)	−0.0010 (7)
N1A	0.0129 (12)	0.0159 (12)	0.0098 (10)	0.0019 (10)	0.0028 (9)	0.0016 (9)
C1B	0.0059 (13)	0.0122 (14)	0.0178 (12)	−0.0018 (11)	−0.0002 (10)	0.0007 (11)
C2B	0.0073 (14)	0.0119 (15)	0.0136 (12)	−0.0040 (11)	−0.0005 (10)	−0.0028 (10)
C3B	0.0047 (14)	0.0135 (14)	0.0149 (12)	−0.0029 (11)	0.0006 (10)	−0.0004 (10)
C4B	0.0057 (13)	0.0094 (13)	0.0197 (13)	−0.0006 (11)	0.0001 (10)	0.0012 (10)
C5B	0.0079 (14)	0.0154 (15)	0.0142 (12)	−0.0013 (12)	0.0028 (10)	−0.0038 (10)
C6B	0.0154 (15)	0.0214 (16)	0.0133 (12)	0.0041 (12)	0.0001 (11)	0.0047 (11)
C7B	0.0157 (15)	0.0135 (14)	0.0197 (13)	0.0018 (12)	−0.0039 (11)	0.0020 (11)
O1B	0.0232 (12)	0.0112 (10)	0.0118 (9)	0.0034 (8)	−0.0010 (8)	−0.0026 (8)
O2B	0.0158 (10)	0.0142 (10)	0.0093 (8)	0.0030 (8)	0.0004 (7)	0.0027 (7)
N1B	0.0121 (12)	0.0135 (12)	0.0110 (10)	−0.0006 (10)	−0.0003 (9)	0.0018 (9)
C8	0.0123 (14)	0.0109 (13)	0.0108 (11)	0.0017 (12)	−0.0018 (10)	−0.0013 (10)
C9	0.0147 (14)	0.0094 (13)	0.0109 (11)	−0.0002 (12)	0.0032 (11)	0.0026 (10)
C10	0.0082 (14)	0.0088 (13)	0.0151 (12)	0.0001 (11)	0.0029 (10)	−0.0027 (10)
C11	0.0137 (15)	0.0093 (13)	0.0117 (11)	0.0007 (11)	−0.0045 (10)	0.0003 (10)
C12	0.0153 (15)	0.0060 (13)	0.0108 (11)	−0.0006 (11)	−0.0004 (10)	−0.0003 (10)
C13	0.0079 (14)	0.0119 (14)	0.0129 (12)	−0.0018 (11)	0.0032 (10)	−0.0036 (10)
O3	0.0087 (11)	0.0214 (11)	0.0177 (9)	−0.0005 (9)	−0.0027 (8)	0.0064 (8)
O4	0.0111 (10)	0.0126 (11)	0.0247 (9)	−0.0029 (9)	−0.0002 (8)	0.0043 (8)
O5	0.0158 (11)	0.0138 (10)	0.0163 (9)	−0.0039 (9)	−0.0034 (8)	0.0065 (8)

Geometric parameters (Å, º)

C1A—C2A	1.373 (3)	C4B—H4B	0.9500
C1A—N1A	1.377 (3)	C5B—N1B	1.344 (3)
C1A—C7A	1.490 (4)	C5B—H5B	0.9500
C2A—O1A	1.355 (3)	C6B—N1B	1.471 (3)
C2A—C3A	1.429 (4)	C6B—H6D	0.9800
C3A—O2A	1.282 (3)	C6B—H6E	0.9800
C3A—C4A	1.413 (3)	C6B—H6F	0.9800
C4A—C5A	1.360 (4)	C7B—H7D	0.9800
C4A—H4A	0.9500	C7B—H7E	0.9800
C5A—N1A	1.342 (3)	C7B—H7F	0.9800
C5A—H5A	0.9500	O1B—H2O	0.86 (3)
C6A—N1A	1.470 (3)	C8—O3	1.372 (3)
C6A—H6A	0.9800	C8—C13	1.385 (3)
C6A—H6B	0.9800	C8—C9	1.388 (4)
C6A—H6C	0.9800	C9—C10	1.386 (3)
C7A—H7A	0.9800	C9—H9	0.9500
C7A—H7B	0.9800	C10—O4	1.372 (3)
C7A—H7C	0.9800	C10—C11	1.388 (3)
O1A—H1O	0.94 (3)	C11—C12	1.388 (4)
C1B—N1B	1.369 (3)	C11—H11	0.9500
C1B—C2B	1.375 (3)	C12—O5	1.368 (3)
C1B—C7B	1.491 (3)	C12—C13	1.392 (3)
C2B—O1B	1.361 (3)	C13—H13	0.9500
C2B—C3B	1.418 (4)	O3—H3O	0.92 (3)
C3B—O2B	1.291 (3)	O4—H4O	0.90 (3)
C3B—C4B	1.405 (3)	O5—H5O	0.98 (4)
C4B—C5B	1.360 (3)
C2A—C1A—N1A	118.7 (2)	C3B—C4B—H4B	119.6
C2A—C1A—C7A	122.6 (2)	N1B—C5B—C4B	121.7 (2)
N1A—C1A—C7A	118.8 (2)	N1B—C5B—H5B	119.2
O1A—C2A—C1A	117.8 (2)	C4B—C5B—H5B	119.2
O1A—C2A—C3A	119.5 (2)	N1B—C6B—H6D	109.5
C1A—C2A—C3A	122.8 (2)	N1B—C6B—H6E	109.5
O2A—C3A—C4A	124.7 (2)	H6D—C6B—H6E	109.5
O2A—C3A—C2A	120.4 (2)	N1B—C6B—H6F	109.5
C4A—C3A—C2A	114.8 (2)	H6D—C6B—H6F	109.5
C5A—C4A—C3A	120.8 (2)	H6E—C6B—H6F	109.5
C5A—C4A—H4A	119.6	C1B—C7B—H7D	109.5
C3A—C4A—H4A	119.6	C1B—C7B—H7E	109.5
N1A—C5A—C4A	122.6 (2)	H7D—C7B—H7E	109.5
N1A—C5A—H5A	118.7	C1B—C7B—H7F	109.5
C4A—C5A—H5A	118.7	H7D—C7B—H7F	109.5
N1A—C6A—H6A	109.5	H7E—C7B—H7F	109.5
N1A—C6A—H6B	109.5	C2B—O1B—H2O	111 (2)
H6A—C6A—H6B	109.5	C5B—N1B—C1B	120.9 (2)
N1A—C6A—H6C	109.5	C5B—N1B—C6B	119.0 (2)
H6A—C6A—H6C	109.5	C1B—N1B—C6B	120.1 (2)
H6B—C6A—H6C	109.5	O3—C8—C13	121.2 (2)
C1A—C7A—H7A	109.5	O3—C8—C9	117.5 (2)
C1A—C7A—H7B	109.5	C13—C8—C9	121.2 (2)
H7A—C7A—H7B	109.5	C10—C9—C8	119.2 (2)
C1A—C7A—H7C	109.5	C10—C9—H9	120.4
H7A—C7A—H7C	109.5	C8—C9—H9	120.4
H7B—C7A—H7C	109.5	O4—C10—C9	120.8 (2)
C2A—O1A—H1O	113.3 (17)	O4—C10—C11	118.2 (2)
C5A—N1A—C1A	120.2 (2)	C9—C10—C11	121.0 (2)
C5A—N1A—C6A	119.3 (2)	C10—C11—C12	118.5 (2)
C1A—N1A—C6A	120.3 (2)	C10—C11—H11	120.7
N1B—C1B—C2B	118.6 (2)	C12—C11—H11	120.7
N1B—C1B—C7B	118.6 (2)	O5—C12—C11	117.5 (2)
C2B—C1B—C7B	122.9 (2)	O5—C12—C13	120.8 (2)
O1B—C2B—C1B	117.9 (2)	C11—C12—C13	121.7 (2)
O1B—C2B—C3B	119.8 (2)	C8—C13—C12	118.3 (2)
C1B—C2B—C3B	122.3 (2)	C8—C13—H13	120.9
O2B—C3B—C4B	124.6 (2)	C12—C13—H13	120.9
O2B—C3B—C2B	119.8 (2)	C8—O3—H3O	112 (2)
C4B—C3B—C2B	115.6 (2)	C10—O4—H4O	111 (2)
C5B—C4B—C3B	120.9 (2)	C12—O5—H5O	110 (2)
C5B—C4B—H4B	119.6
N1A—C1A—C2A—O1A	−177.8 (2)	O1B—C2B—C3B—C4B	178.3 (2)
C7A—C1A—C2A—O1A	2.6 (3)	C1B—C2B—C3B—C4B	−2.7 (4)
N1A—C1A—C2A—C3A	3.8 (4)	O2B—C3B—C4B—C5B	−179.2 (2)
C7A—C1A—C2A—C3A	−175.8 (2)	C2B—C3B—C4B—C5B	2.1 (4)
O1A—C2A—C3A—O2A	−1.2 (3)	C3B—C4B—C5B—N1B	0.7 (4)
C1A—C2A—C3A—O2A	177.2 (2)	C4B—C5B—N1B—C1B	−3.2 (4)
O1A—C2A—C3A—C4A	178.6 (2)	C4B—C5B—N1B—C6B	176.1 (2)
C1A—C2A—C3A—C4A	−3.0 (3)	C2B—C1B—N1B—C5B	2.5 (4)
O2A—C3A—C4A—C5A	−179.3 (2)	C7B—C1B—N1B—C5B	−176.0 (2)
C2A—C3A—C4A—C5A	0.9 (3)	C2B—C1B—N1B—C6B	−176.8 (2)
C3A—C4A—C5A—N1A	0.2 (4)	C7B—C1B—N1B—C6B	4.7 (3)
C4A—C5A—N1A—C1A	0.5 (4)	O3—C8—C9—C10	179.9 (2)
C4A—C5A—N1A—C6A	177.0 (2)	C13—C8—C9—C10	1.7 (4)
C2A—C1A—N1A—C5A	−2.5 (3)	C8—C9—C10—O4	177.9 (2)
C7A—C1A—N1A—C5A	177.1 (2)	C8—C9—C10—C11	−1.9 (4)
C2A—C1A—N1A—C6A	−178.9 (2)	O4—C10—C11—C12	−179.2 (2)
C7A—C1A—N1A—C6A	0.7 (3)	C9—C10—C11—C12	0.7 (4)
N1B—C1B—C2B—O1B	179.5 (2)	C10—C11—C12—O5	−179.4 (2)
C7B—C1B—C2B—O1B	−2.1 (4)	C10—C11—C12—C13	0.8 (4)
N1B—C1B—C2B—C3B	0.4 (4)	O3—C8—C13—C12	−178.3 (2)
C7B—C1B—C2B—C3B	178.9 (2)	C9—C8—C13—C12	−0.2 (4)
O1B—C2B—C3B—O2B	−0.5 (4)	O5—C12—C13—C8	179.1 (2)
C1B—C2B—C3B—O2B	178.5 (2)	C11—C12—C13—C8	−1.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O···O2B	0.94 (3)	1.78 (3)	2.668 (2)	156 (3)
O1B—H2O···O2A	0.86 (3)	1.90 (3)	2.700 (2)	154 (3)
O1B—H2O···O2B	0.86 (3)	2.31 (3)	2.736 (2)	111 (2)
O3—H3O···O4^i	0.92 (3)	1.92 (3)	2.769 (3)	154 (3)
O4—H4O···O2B^ii	0.90 (3)	1.69 (3)	2.590 (2)	175 (3)
O5—H5O···O2A	0.98 (4)	1.67 (4)	2.641 (3)	172 (3)
C5B—H5B···O3^iii	0.95	2.57	3.258 (3)	129
C6B—H6E···O1A^iv	0.98	2.55	3.323 (3)	136

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

(KA1017_0m_def-phghyd_2_1_2)

Crystal data

2(C7H9NO2)·C6H6O3·2(H2O)	Z = 2
Mr = 440.44	F(000) = 468
Triclinic, P1	Dx = 1.398 Mg m^−3
a = 7.9892 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.197 (3) Å	Cell parameters from 9849 reflections
c = 12.876 (4) Å	θ = 2.5–30.5°
α = 91.088 (8)°	µ = 0.11 mm^−1
β = 93.874 (7)°	T = 100 K
γ = 90.209 (7)°	Block, colorless
V = 1046.4 (5) Å^3	0.32 × 0.26 × 0.17 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	4349 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.057
ω and φ scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −9→10
Tmin = 0.538, Tmax = 0.746	k = −13→13
20542 measured reflections	l = −16→16
4542 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.084	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.205	w = 1/[σ^2(Fo^2) + 4.4439P] where P = (Fo^2 + 2Fc^2)/3
S = 1.25	(Δ/σ)max < 0.001
4542 reflections	Δρmax = 0.48 e Å^−3
300 parameters	Δρmin = −0.56 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	0.7653 (4)	0.5446 (3)	1.2756 (2)	0.0103 (6)
C2A	0.6792 (4)	0.5415 (3)	1.1793 (2)	0.0106 (6)
C3A	0.6705 (4)	0.6539 (3)	1.1136 (3)	0.0118 (6)
C4A	0.7611 (4)	0.7654 (3)	1.1533 (3)	0.0159 (7)
H4A	0.762921	0.842147	1.112628	0.019*
C5A	0.8460 (4)	0.7648 (3)	1.2490 (3)	0.0158 (7)
H5A	0.905462	0.841341	1.273594	0.019*
C6A	0.9337 (4)	0.6654 (4)	1.4150 (3)	0.0175 (7)
H6A	1.013010	0.592687	1.423615	0.026*
H6B	0.850697	0.659934	1.467449	0.026*
H6C	0.994574	0.748908	1.423700	0.026*
C7A	0.7710 (5)	0.4277 (3)	1.3451 (3)	0.0163 (7)
H7A	0.697749	0.358410	1.313651	0.024*
H7B	0.732598	0.453297	1.413248	0.024*
H7C	0.886330	0.395327	1.353705	0.024*
N1A	0.8474 (3)	0.6573 (3)	1.3097 (2)	0.0129 (6)
O1A	0.5992 (3)	0.4286 (2)	1.14639 (19)	0.0139 (5)
O2A	0.5843 (3)	0.6491 (2)	1.02570 (18)	0.0149 (5)
H1OA	0.551 (7)	0.439 (5)	1.084 (4)	0.044 (15)*
C1B	0.2381 (4)	0.5294 (3)	0.2286 (3)	0.0153 (7)
C2B	0.3228 (5)	0.5350 (3)	0.3240 (3)	0.0167 (7)
C3B	0.4026 (4)	0.6531 (3)	0.3660 (3)	0.0154 (7)
C4B	0.3821 (4)	0.7644 (3)	0.3016 (3)	0.0164 (7)
H4B	0.428248	0.846557	0.325218	0.020*
C5B	0.2969 (5)	0.7547 (3)	0.2065 (3)	0.0168 (7)
H5B	0.286583	0.830421	0.164751	0.020*
C6B	0.1424 (5)	0.6351 (4)	0.0642 (3)	0.0204 (7)
H6D	0.144101	0.722251	0.033457	0.031*
H6E	0.026000	0.606206	0.068303	0.031*
H6F	0.201202	0.572865	0.020752	0.031*
C7B	0.1576 (5)	0.4051 (3)	0.1844 (3)	0.0205 (7)
H7D	0.038753	0.421044	0.164962	0.031*
H7E	0.167422	0.336550	0.236714	0.031*
H7F	0.214041	0.376744	0.122612	0.031*
N1B	0.2267 (4)	0.6412 (3)	0.1696 (2)	0.0149 (6)
O1B	0.3299 (4)	0.4240 (2)	0.3812 (2)	0.0216 (6)
H1OB	0.402 (6)	0.433 (4)	0.434 (3)	0.015 (10)*
O2B	0.4837 (3)	0.6542 (2)	0.45484 (19)	0.0194 (5)
C8	0.0720 (4)	0.8999 (3)	0.6541 (2)	0.0101 (6)
C9	−0.1014 (4)	0.9102 (3)	0.6534 (2)	0.0111 (6)
H9	−0.168462	0.911490	0.589668	0.013*
C10	−0.1745 (4)	0.9187 (3)	0.7484 (2)	0.0075 (6)
C11	−0.0789 (4)	0.9219 (3)	0.8429 (2)	0.0100 (6)
H11	−0.130662	0.931263	0.906883	0.012*
C12	0.0949 (4)	0.9109 (3)	0.8411 (2)	0.0094 (6)
C13	0.1722 (4)	0.8992 (3)	0.7472 (2)	0.0099 (6)
H13	0.290568	0.890981	0.746785	0.012*
O3	0.1396 (3)	0.8906 (3)	0.56004 (18)	0.0190 (6)
H3O	0.249 (7)	0.890 (5)	0.569 (4)	0.035 (14)*
O4	−0.3468 (3)	0.9221 (2)	0.74928 (17)	0.0112 (5)
H4O	−0.383223	0.933341	0.687952	0.017*
O5	0.1849 (3)	0.9122 (2)	0.93497 (18)	0.0136 (5)
H5O	0.283 (8)	0.911 (6)	0.930 (5)	0.056 (19)*
O1W	0.4799 (3)	0.8860 (2)	0.55806 (18)	0.0127 (5)
H1W	0.491418	0.813132	0.524821	0.019*
H2W	0.535172	0.877486	0.625250	0.019*	0.5
H2WD	0.492888	0.952574	0.520027	0.019*	0.5
O2W	0.5173 (3)	0.8819 (2)	0.93695 (17)	0.0136 (5)
H3W	0.541136	0.810013	0.966539	0.020*
H4W	0.558828	0.894838	0.873059	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0099 (14)	0.0059 (14)	0.0152 (15)	−0.0021 (11)	0.0001 (11)	−0.0002 (11)
C2A	0.0071 (14)	0.0098 (14)	0.0148 (15)	−0.0014 (11)	0.0004 (11)	−0.0014 (11)
C3A	0.0102 (14)	0.0099 (15)	0.0155 (15)	0.0007 (11)	0.0019 (12)	0.0005 (12)
C4A	0.0151 (16)	0.0096 (15)	0.0230 (17)	−0.0018 (12)	−0.0011 (13)	0.0046 (13)
C5A	0.0121 (15)	0.0107 (15)	0.0242 (17)	−0.0028 (12)	−0.0010 (13)	0.0010 (13)
C6A	0.0140 (16)	0.0190 (17)	0.0181 (17)	−0.0020 (13)	−0.0080 (13)	−0.0029 (13)
C7A	0.0216 (17)	0.0122 (15)	0.0147 (15)	0.0002 (13)	−0.0026 (13)	0.0022 (12)
N1A	0.0107 (13)	0.0114 (13)	0.0159 (13)	−0.0008 (10)	−0.0030 (10)	−0.0016 (10)
O1A	0.0184 (12)	0.0080 (11)	0.0145 (11)	−0.0041 (9)	−0.0046 (9)	0.0003 (9)
O2A	0.0169 (12)	0.0123 (11)	0.0148 (11)	−0.0003 (9)	−0.0040 (9)	0.0025 (9)
C1B	0.0192 (17)	0.0098 (15)	0.0181 (16)	0.0060 (12)	0.0087 (13)	0.0044 (12)
C2B	0.0231 (18)	0.0132 (16)	0.0149 (15)	0.0084 (13)	0.0075 (13)	0.0059 (12)
C3B	0.0204 (17)	0.0123 (16)	0.0141 (15)	0.0078 (13)	0.0052 (13)	0.0019 (12)
C4B	0.0223 (17)	0.0102 (15)	0.0173 (16)	0.0030 (13)	0.0036 (13)	0.0036 (12)
C5B	0.0234 (18)	0.0086 (15)	0.0192 (16)	0.0047 (13)	0.0052 (14)	0.0051 (12)
C6B	0.0283 (19)	0.0182 (17)	0.0155 (16)	0.0072 (14)	0.0046 (14)	0.0062 (13)
C7B	0.0289 (19)	0.0145 (17)	0.0184 (17)	0.0027 (14)	0.0036 (14)	0.0026 (13)
N1B	0.0192 (14)	0.0140 (14)	0.0119 (13)	0.0058 (11)	0.0026 (11)	0.0045 (11)
O1B	0.0349 (16)	0.0105 (12)	0.0191 (13)	−0.0005 (10)	−0.0033 (11)	0.0063 (10)
O2B	0.0287 (14)	0.0146 (12)	0.0147 (12)	0.0082 (10)	−0.0014 (10)	0.0026 (9)
C8	0.0135 (15)	0.0088 (14)	0.0081 (14)	−0.0015 (11)	0.0011 (11)	−0.0019 (11)
C9	0.0097 (14)	0.0122 (15)	0.0110 (14)	0.0006 (11)	−0.0016 (11)	0.0018 (11)
C10	0.0062 (13)	0.0024 (12)	0.0137 (14)	−0.0023 (10)	0.0005 (11)	0.0002 (10)
C11	0.0117 (15)	0.0078 (14)	0.0108 (14)	−0.0016 (11)	0.0023 (11)	0.0000 (11)
C12	0.0116 (14)	0.0057 (13)	0.0108 (14)	−0.0013 (11)	−0.0007 (11)	0.0019 (11)
C13	0.0074 (14)	0.0103 (14)	0.0119 (14)	0.0010 (11)	−0.0009 (11)	−0.0008 (11)
O3	0.0092 (12)	0.0377 (15)	0.0102 (11)	−0.0008 (10)	0.0017 (9)	−0.0033 (10)
O4	0.0064 (10)	0.0152 (11)	0.0118 (10)	0.0001 (8)	−0.0013 (8)	0.0013 (8)
O5	0.0102 (12)	0.0183 (12)	0.0118 (11)	−0.0017 (9)	−0.0025 (9)	0.0009 (9)
O1W	0.0121 (11)	0.0101 (11)	0.0159 (11)	0.0001 (8)	0.0003 (9)	0.0017 (8)
O2W	0.0177 (12)	0.0099 (11)	0.0125 (11)	0.0008 (9)	−0.0038 (9)	0.0029 (8)

Geometric parameters (Å, º)

C1A—N1A	1.371 (4)	C5B—H5B	0.9500
C1A—C2A	1.377 (4)	C6B—N1B	1.474 (4)
C1A—C7A	1.503 (4)	C6B—H6D	0.9800
C2A—O1A	1.361 (4)	C6B—H6E	0.9800
C2A—C3A	1.437 (4)	C6B—H6F	0.9800
C3A—O2A	1.285 (4)	C7B—H7D	0.9800
C3A—C4A	1.414 (5)	C7B—H7E	0.9800
C4A—C5A	1.366 (5)	C7B—H7F	0.9800
C4A—H4A	0.9500	O1B—H1OB	0.86 (4)
C5A—N1A	1.359 (4)	C8—O3	1.362 (4)
C5A—H5A	0.9500	C8—C9	1.389 (4)
C6A—N1A	1.480 (4)	C8—C13	1.396 (4)
C6A—H6A	0.9800	C9—C10	1.392 (4)
C6A—H6B	0.9800	C9—H9	0.9500
C6A—H6C	0.9800	C10—O4	1.379 (4)
C7A—H7A	0.9800	C10—C11	1.391 (4)
C7A—H7B	0.9800	C11—C12	1.395 (4)
C7A—H7C	0.9800	C11—H11	0.9500
O1A—H1OA	0.87 (6)	C12—O5	1.364 (4)
C1B—C2B	1.362 (5)	C12—C13	1.397 (4)
C1B—N1B	1.381 (4)	C13—H13	0.9500
C1B—C7B	1.504 (5)	O3—H3O	0.87 (6)
C2B—O1B	1.362 (4)	O4—H4O	0.8330
C2B—C3B	1.439 (5)	O5—H5O	0.79 (7)
C3B—O2B	1.276 (4)	O1W—H1W	0.8584
C3B—C4B	1.422 (4)	O1W—H2W	0.9500
C4B—C5B	1.362 (5)	O1W—H2WD	0.8550
C4B—H4B	0.9500	O2W—H3W	0.8487
C5B—N1B	1.349 (5)	O2W—H4W	0.9192
N1A—C1A—C2A	119.4 (3)	N1B—C5B—H5B	118.9
N1A—C1A—C7A	118.9 (3)	C4B—C5B—H5B	118.9
C2A—C1A—C7A	121.7 (3)	N1B—C6B—H6D	109.5
O1A—C2A—C1A	118.7 (3)	N1B—C6B—H6E	109.5
O1A—C2A—C3A	119.5 (3)	H6D—C6B—H6E	109.5
C1A—C2A—C3A	121.8 (3)	N1B—C6B—H6F	109.5
O2A—C3A—C4A	124.3 (3)	H6D—C6B—H6F	109.5
O2A—C3A—C2A	120.3 (3)	H6E—C6B—H6F	109.5
C4A—C3A—C2A	115.4 (3)	C1B—C7B—H7D	109.5
C5A—C4A—C3A	121.2 (3)	C1B—C7B—H7E	109.5
C5A—C4A—H4A	119.4	H7D—C7B—H7E	109.5
C3A—C4A—H4A	119.4	C1B—C7B—H7F	109.5
N1A—C5A—C4A	121.5 (3)	H7D—C7B—H7F	109.5
N1A—C5A—H5A	119.3	H7E—C7B—H7F	109.5
C4A—C5A—H5A	119.3	C5B—N1B—C1B	120.4 (3)
N1A—C6A—H6A	109.5	C5B—N1B—C6B	119.8 (3)
N1A—C6A—H6B	109.5	C1B—N1B—C6B	119.8 (3)
H6A—C6A—H6B	109.5	C2B—O1B—H1OB	110 (3)
N1A—C6A—H6C	109.5	O3—C8—C9	117.0 (3)
H6A—C6A—H6C	109.5	O3—C8—C13	121.6 (3)
H6B—C6A—H6C	109.5	C9—C8—C13	121.4 (3)
C1A—C7A—H7A	109.5	C8—C9—C10	118.4 (3)
C1A—C7A—H7B	109.5	C8—C9—H9	120.8
H7A—C7A—H7B	109.5	C10—C9—H9	120.8
C1A—C7A—H7C	109.5	O4—C10—C11	118.8 (3)
H7A—C7A—H7C	109.5	O4—C10—C9	119.1 (3)
H7B—C7A—H7C	109.5	C11—C10—C9	122.0 (3)
C5A—N1A—C1A	120.6 (3)	C10—C11—C12	118.2 (3)
C5A—N1A—C6A	118.8 (3)	C10—C11—H11	120.9
C1A—N1A—C6A	120.5 (3)	C12—C11—H11	120.9
C2A—O1A—H1OA	109 (4)	O5—C12—C11	116.9 (3)
C2B—C1B—N1B	119.2 (3)	O5—C12—C13	121.9 (3)
C2B—C1B—C7B	122.3 (3)	C11—C12—C13	121.3 (3)
N1B—C1B—C7B	118.6 (3)	C8—C13—C12	118.6 (3)
O1B—C2B—C1B	117.9 (3)	C8—C13—H13	120.7
O1B—C2B—C3B	119.5 (3)	C12—C13—H13	120.7
C1B—C2B—C3B	122.5 (3)	C8—O3—H3O	110 (3)
O2B—C3B—C4B	124.2 (3)	C10—O4—H4O	106.4
O2B—C3B—C2B	120.9 (3)	C12—O5—H5O	113 (4)
C4B—C3B—C2B	114.9 (3)	H1W—O1W—H2W	107.5
C5B—C4B—C3B	120.7 (3)	H1W—O1W—H2WD	112.5
C5B—C4B—H4B	119.6	H2W—O1W—H2WD	122.9
C3B—C4B—H4B	119.6	H3W—O2W—H4W	117.2
N1B—C5B—C4B	122.2 (3)
N1A—C1A—C2A—O1A	179.7 (3)	O1B—C2B—C3B—C4B	−177.7 (3)
C7A—C1A—C2A—O1A	−0.8 (5)	C1B—C2B—C3B—C4B	1.8 (5)
N1A—C1A—C2A—C3A	−0.9 (5)	O2B—C3B—C4B—C5B	178.4 (3)
C7A—C1A—C2A—C3A	178.6 (3)	C2B—C3B—C4B—C5B	−2.0 (5)
O1A—C2A—C3A—O2A	1.8 (5)	C3B—C4B—C5B—N1B	0.9 (5)
C1A—C2A—C3A—O2A	−177.6 (3)	C4B—C5B—N1B—C1B	0.6 (5)
O1A—C2A—C3A—C4A	−178.4 (3)	C4B—C5B—N1B—C6B	−177.3 (3)
C1A—C2A—C3A—C4A	2.1 (5)	C2B—C1B—N1B—C5B	−0.8 (5)
O2A—C3A—C4A—C5A	178.0 (3)	C7B—C1B—N1B—C5B	179.9 (3)
C2A—C3A—C4A—C5A	−1.8 (5)	C2B—C1B—N1B—C6B	177.1 (3)
C3A—C4A—C5A—N1A	0.2 (5)	C7B—C1B—N1B—C6B	−2.3 (5)
C4A—C5A—N1A—C1A	1.2 (5)	O3—C8—C9—C10	179.4 (3)
C4A—C5A—N1A—C6A	−176.6 (3)	C13—C8—C9—C10	−0.6 (5)
C2A—C1A—N1A—C5A	−0.8 (5)	C8—C9—C10—O4	−176.7 (3)
C7A—C1A—N1A—C5A	179.6 (3)	C8—C9—C10—C11	2.4 (5)
C2A—C1A—N1A—C6A	176.9 (3)	O4—C10—C11—C12	176.4 (3)
C7A—C1A—N1A—C6A	−2.6 (4)	C9—C10—C11—C12	−2.6 (4)
N1B—C1B—C2B—O1B	179.1 (3)	C10—C11—C12—O5	−179.0 (3)
C7B—C1B—C2B—O1B	−1.6 (5)	C10—C11—C12—C13	1.1 (4)
N1B—C1B—C2B—C3B	−0.5 (5)	O3—C8—C13—C12	179.2 (3)
C7B—C1B—C2B—C3B	178.9 (3)	C9—C8—C13—C12	−0.8 (5)
O1B—C2B—C3B—O2B	1.9 (5)	O5—C12—C13—C8	−179.3 (3)
C1B—C2B—C3B—O2B	−178.6 (3)	C11—C12—C13—C8	0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···O2A	0.87 (6)	2.30 (6)	2.756 (3)	113 (4)
O1A—H1OA···O2A^i	0.87 (6)	1.93 (6)	2.678 (3)	143 (5)
O1B—H1OB···O2B^ii	0.86 (4)	1.89 (4)	2.638 (4)	145 (4)
O3—H3O···O1W	0.87 (6)	1.86 (6)	2.721 (3)	168 (5)
O4—H4O···O1W^iii	0.83	1.99	2.760 (3)	154
O5—H5O···O2W	0.79 (7)	1.90 (7)	2.673 (3)	168 (6)
O1W—H1W···O2B	0.86	1.84	2.690 (3)	172
O1W—H2W···O4^iv	0.95	1.85	2.760 (3)	160
O1W—H2WD···O1W^v	0.85	1.96	2.818 (5)	176
O2W—H3W···O2A	0.85	1.85	2.693 (3)	177
O2W—H4W···O4^iv	0.92	1.83	2.752 (3)	177

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

(KA803_0m_def-pyro_1_2)

Crystal data

C7H9NO2·2(C6H6O3)	F(000) = 1648
Mr = 391.37	Dx = 1.431 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 28.0626 (4) Å	Cell parameters from 9898 reflections
b = 9.2719 (1) Å	θ = 2.6–30.6°
c = 14.6075 (2) Å	µ = 0.11 mm^−1
β = 107.0808 (5)°	T = 100 K
V = 3633.13 (8) Å^3	Needle, colorless
Z = 8	0.32 × 0.18 × 0.16 mm

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	3357 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.027
ω and φ scans	θmax = 26.3°, θmin = 2.3°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −34→34
Tmin = 0.693, Tmax = 0.746	k = −11→11
23872 measured reflections	l = −18→18
3664 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0563P)^2 + 2.7534P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3664 reflections	Δρmax = 0.43 e Å^−3
283 parameters	Δρmin = −0.30 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	0.43916 (4)	−0.07673 (12)	1.02071 (8)	0.0132 (2)
C2	0.44400 (4)	0.07094 (12)	1.02368 (7)	0.0117 (2)
C3	0.44137 (4)	0.15283 (12)	0.93988 (7)	0.0113 (2)
C4	0.43261 (4)	0.07434 (13)	0.85397 (8)	0.0145 (2)
H4	0.429760	0.123952	0.795703	0.017*
C5	0.42819 (4)	−0.07221 (13)	0.85358 (8)	0.0158 (2)
H5	0.422651	−0.123025	0.794902	0.019*
C6	0.42792 (4)	−0.30550 (13)	0.93044 (9)	0.0205 (3)
H6A	0.418201	−0.336831	0.863421	0.031*
H6B	0.402856	−0.337643	0.960631	0.031*
H6C	0.460343	−0.347465	0.964452	0.031*
C7	0.44205 (5)	−0.16221 (13)	1.10874 (9)	0.0193 (2)
H7A	0.453893	−0.100239	1.165233	0.029*
H7B	0.465237	−0.242826	1.113520	0.029*
H7C	0.408913	−0.199693	1.105288	0.029*
O1	0.45241 (3)	0.13873 (9)	1.10948 (5)	0.01534 (18)
H1O	0.4552 (6)	0.230 (2)	1.0988 (12)	0.034 (4)*
O2	0.44709 (3)	0.29148 (8)	0.94658 (5)	0.01268 (18)
N1	0.43149 (3)	−0.14677 (10)	0.93469 (7)	0.0144 (2)
C8A	0.41139 (4)	0.45227 (11)	0.73380 (7)	0.0107 (2)
C9A	0.41208 (4)	0.52017 (11)	0.64935 (7)	0.0107 (2)
C10A	0.36733 (4)	0.55132 (12)	0.57936 (7)	0.0126 (2)
C11A	0.32198 (4)	0.51724 (13)	0.59421 (8)	0.0159 (2)
H11A	0.291544	0.539665	0.546996	0.019*
C12A	0.32171 (4)	0.44987 (13)	0.67907 (8)	0.0168 (2)
H12A	0.290803	0.426236	0.689604	0.020*
C13A	0.36601 (4)	0.41654 (12)	0.74881 (8)	0.0142 (2)
H13A	0.365352	0.369731	0.806273	0.017*
O3A	0.45640 (3)	0.42227 (8)	0.79924 (5)	0.01282 (18)
H2O	0.4516 (7)	0.374 (2)	0.8531 (13)	0.043 (5)*
O4A	0.45549 (3)	0.56065 (9)	0.63061 (6)	0.01373 (18)
H3O	0.4815 (7)	0.5131 (19)	0.6648 (13)	0.037 (5)*
O5A	0.36726 (3)	0.61355 (9)	0.49454 (5)	0.01565 (18)
H40	0.3971 (7)	0.629 (2)	0.4928 (13)	0.039 (5)*
C8B	0.30615 (4)	1.02767 (13)	0.28780 (8)	0.0172 (2)
C9B	0.30945 (4)	0.94795 (13)	0.37025 (8)	0.0148 (2)
C10B	0.30958 (4)	1.01835 (13)	0.45470 (8)	0.0171 (2)
C11B	0.30578 (4)	1.16756 (14)	0.45566 (9)	0.0213 (3)
H11B	0.305663	1.216281	0.512810	0.026*
C12B	0.30212 (4)	1.24557 (14)	0.37222 (10)	0.0234 (3)
H12B	0.299365	1.347647	0.373056	0.028*
C13B	0.30244 (4)	1.17663 (14)	0.28774 (9)	0.0217 (3)
H13B	0.300172	1.230551	0.231318	0.026*
O3B	0.30700 (3)	0.95430 (11)	0.20586 (6)	0.0233 (2)
H5O	0.3088 (7)	0.861 (2)	0.2211 (14)	0.047 (5)*
O4B	0.31178 (3)	0.80175 (9)	0.36250 (6)	0.01821 (19)
H6O	0.3236 (7)	0.760 (2)	0.4197 (15)	0.048 (5)*
O5B	0.31351 (3)	0.92959 (10)	0.53142 (6)	0.0233 (2)
H7O	0.3116 (7)	0.978 (2)	0.5838 (15)	0.049 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0099 (5)	0.0151 (5)	0.0152 (5)	0.0009 (4)	0.0047 (4)	0.0005 (4)
C2	0.0098 (5)	0.0148 (5)	0.0111 (5)	0.0011 (4)	0.0040 (4)	−0.0007 (4)
C3	0.0079 (5)	0.0137 (5)	0.0127 (5)	0.0014 (4)	0.0038 (4)	0.0006 (4)
C4	0.0144 (5)	0.0186 (6)	0.0110 (5)	0.0010 (4)	0.0046 (4)	0.0007 (4)
C5	0.0138 (5)	0.0199 (6)	0.0136 (5)	0.0007 (4)	0.0037 (4)	−0.0043 (4)
C6	0.0202 (6)	0.0124 (6)	0.0279 (6)	0.0003 (4)	0.0052 (5)	−0.0038 (5)
C7	0.0232 (6)	0.0159 (6)	0.0209 (6)	0.0015 (5)	0.0099 (5)	0.0050 (4)
O1	0.0226 (4)	0.0143 (4)	0.0099 (4)	0.0006 (3)	0.0059 (3)	−0.0003 (3)
O2	0.0149 (4)	0.0119 (4)	0.0120 (4)	−0.0004 (3)	0.0051 (3)	0.0008 (3)
N1	0.0131 (4)	0.0126 (5)	0.0179 (5)	0.0002 (3)	0.0049 (4)	−0.0021 (4)
C8A	0.0105 (5)	0.0097 (5)	0.0112 (5)	0.0005 (4)	0.0020 (4)	−0.0017 (4)
C9A	0.0099 (5)	0.0102 (5)	0.0130 (5)	−0.0002 (4)	0.0049 (4)	−0.0012 (4)
C10A	0.0142 (5)	0.0119 (5)	0.0116 (5)	0.0008 (4)	0.0036 (4)	0.0009 (4)
C11A	0.0107 (5)	0.0201 (6)	0.0155 (5)	0.0007 (4)	0.0015 (4)	0.0014 (4)
C12A	0.0115 (5)	0.0204 (6)	0.0196 (6)	−0.0023 (4)	0.0062 (4)	0.0007 (4)
C13A	0.0148 (5)	0.0162 (5)	0.0129 (5)	−0.0016 (4)	0.0061 (4)	0.0018 (4)
O3A	0.0101 (4)	0.0170 (4)	0.0108 (4)	−0.0002 (3)	0.0020 (3)	0.0035 (3)
O4A	0.0097 (4)	0.0170 (4)	0.0153 (4)	0.0013 (3)	0.0049 (3)	0.0066 (3)
O5A	0.0125 (4)	0.0218 (4)	0.0124 (4)	0.0016 (3)	0.0033 (3)	0.0062 (3)
C8B	0.0105 (5)	0.0247 (6)	0.0159 (5)	0.0009 (4)	0.0032 (4)	0.0021 (5)
C9B	0.0095 (5)	0.0177 (6)	0.0165 (5)	0.0024 (4)	0.0026 (4)	0.0013 (4)
C10B	0.0112 (5)	0.0231 (6)	0.0166 (5)	0.0020 (4)	0.0036 (4)	0.0005 (5)
C11B	0.0138 (5)	0.0235 (6)	0.0260 (6)	0.0006 (5)	0.0050 (5)	−0.0058 (5)
C12B	0.0144 (5)	0.0174 (6)	0.0368 (7)	0.0005 (5)	0.0049 (5)	0.0003 (5)
C13B	0.0138 (5)	0.0235 (6)	0.0261 (6)	0.0005 (5)	0.0034 (5)	0.0085 (5)
O3B	0.0299 (5)	0.0261 (5)	0.0146 (4)	0.0000 (4)	0.0078 (3)	0.0040 (4)
O4B	0.0239 (4)	0.0180 (4)	0.0124 (4)	0.0056 (3)	0.0049 (3)	0.0018 (3)
O5B	0.0325 (5)	0.0255 (5)	0.0134 (4)	0.0049 (4)	0.0091 (4)	−0.0002 (3)

Geometric parameters (Å, º)

C1—N1	1.3741 (14)	C10A—C11A	1.3888 (15)
C1—C2	1.3753 (16)	C11A—C12A	1.3901 (16)
C1—C7	1.4924 (15)	C11A—H11A	0.9500
C2—O1	1.3593 (13)	C12A—C13A	1.3909 (16)
C2—C3	1.4238 (15)	C12A—H12A	0.9500
C3—O2	1.2957 (14)	C13A—H13A	0.9500
C3—C4	1.4084 (15)	O3A—H2O	0.95 (2)
C4—C5	1.3643 (17)	O4A—H3O	0.872 (19)
C4—H4	0.9500	O5A—H40	0.858 (19)
C5—N1	1.3513 (15)	C8B—O3B	1.3831 (15)
C5—H5	0.9500	C8B—C13B	1.3850 (18)
C6—N1	1.4752 (15)	C8B—C9B	1.3928 (16)
C6—H6A	0.9800	C9B—O4B	1.3634 (14)
C6—H6B	0.9800	C9B—C10B	1.3947 (16)
C6—H6C	0.9800	C10B—O5B	1.3684 (15)
C7—H7A	0.9800	C10B—C11B	1.3880 (18)
C7—H7B	0.9800	C11B—C12B	1.3950 (19)
C7—H7C	0.9800	C11B—H11B	0.9500
O1—H1O	0.872 (19)	C12B—C13B	1.3920 (19)
C8A—O3A	1.3701 (12)	C12B—H12B	0.9500
C8A—C9A	1.3901 (15)	C13B—H13B	0.9500
C8A—C13A	1.3940 (15)	O3B—H5O	0.89 (2)
C9A—O4A	1.3769 (12)	O4B—H6O	0.89 (2)
C9A—C10A	1.3969 (15)	O5B—H7O	0.91 (2)
C10A—O5A	1.3662 (13)
N1—C1—C2	119.14 (10)	O5A—C10A—C11A	118.71 (9)
N1—C1—C7	119.42 (10)	O5A—C10A—C9A	120.84 (9)
C2—C1—C7	121.44 (10)	C11A—C10A—C9A	120.44 (10)
O1—C2—C1	118.57 (9)	C10A—C11A—C12A	119.13 (10)
O1—C2—C3	119.82 (10)	C10A—C11A—H11A	120.4
C1—C2—C3	121.60 (10)	C12A—C11A—H11A	120.4
O2—C3—C4	124.42 (10)	C11A—C12A—C13A	121.01 (10)
O2—C3—C2	119.35 (9)	C11A—C12A—H12A	119.5
C4—C3—C2	116.23 (10)	C13A—C12A—H12A	119.5
C5—C4—C3	120.68 (10)	C12A—C13A—C8A	119.55 (10)
C5—C4—H4	119.7	C12A—C13A—H13A	120.2
C3—C4—H4	119.7	C8A—C13A—H13A	120.2
N1—C5—C4	121.54 (10)	C8A—O3A—H2O	110.4 (11)
N1—C5—H5	119.2	C9A—O4A—H3O	112.8 (12)
C4—C5—H5	119.2	C10A—O5A—H40	110.9 (12)
N1—C6—H6A	109.5	O3B—C8B—C13B	120.69 (11)
N1—C6—H6B	109.5	O3B—C8B—C9B	118.27 (11)
H6A—C6—H6B	109.5	C13B—C8B—C9B	121.04 (11)
N1—C6—H6C	109.5	O4B—C9B—C8B	116.64 (10)
H6A—C6—H6C	109.5	O4B—C9B—C10B	123.44 (10)
H6B—C6—H6C	109.5	C8B—C9B—C10B	119.91 (11)
C1—C7—H7A	109.5	O5B—C10B—C11B	125.39 (11)
C1—C7—H7B	109.5	O5B—C10B—C9B	114.93 (10)
H7A—C7—H7B	109.5	C11B—C10B—C9B	119.68 (11)
C1—C7—H7C	109.5	C10B—C11B—C12B	119.61 (11)
H7A—C7—H7C	109.5	C10B—C11B—H11B	120.2
H7B—C7—H7C	109.5	C12B—C11B—H11B	120.2
C2—O1—H1O	106.6 (11)	C13B—C12B—C11B	121.23 (12)
C5—N1—C1	120.80 (10)	C13B—C12B—H12B	119.4
C5—N1—C6	119.15 (10)	C11B—C12B—H12B	119.4
C1—N1—C6	120.03 (10)	C8B—C13B—C12B	118.51 (11)
O3A—C8A—C9A	117.44 (9)	C8B—C13B—H13B	120.7
O3A—C8A—C13A	122.65 (9)	C12B—C13B—H13B	120.7
C9A—C8A—C13A	119.92 (9)	C8B—O3B—H5O	106.0 (12)
O4A—C9A—C8A	122.93 (9)	C9B—O4B—H6O	111.4 (13)
O4A—C9A—C10A	117.11 (9)	C10B—O5B—H7O	112.4 (13)
C8A—C9A—C10A	119.95 (9)
N1—C1—C2—O1	−178.89 (9)	O4A—C9A—C10A—C11A	−178.29 (10)
C7—C1—C2—O1	1.11 (15)	C8A—C9A—C10A—C11A	1.16 (16)
N1—C1—C2—C3	−0.14 (15)	O5A—C10A—C11A—C12A	178.05 (10)
C7—C1—C2—C3	179.86 (9)	C9A—C10A—C11A—C12A	−0.90 (17)
O1—C2—C3—O2	0.05 (14)	C10A—C11A—C12A—C13A	0.05 (17)
C1—C2—C3—O2	−178.69 (9)	C11A—C12A—C13A—C8A	0.55 (17)
O1—C2—C3—C4	179.91 (9)	O3A—C8A—C13A—C12A	−179.79 (10)
C1—C2—C3—C4	1.17 (15)	C9A—C8A—C13A—C12A	−0.29 (16)
O2—C3—C4—C5	178.42 (10)	O3B—C8B—C9B—O4B	−1.93 (15)
C2—C3—C4—C5	−1.43 (15)	C13B—C8B—C9B—O4B	178.50 (10)
C3—C4—C5—N1	0.69 (17)	O3B—C8B—C9B—C10B	178.90 (10)
C4—C5—N1—C1	0.43 (16)	C13B—C8B—C9B—C10B	−0.67 (16)
C4—C5—N1—C6	−178.18 (10)	O4B—C9B—C10B—O5B	1.57 (15)
C2—C1—N1—C5	−0.69 (15)	C8B—C9B—C10B—O5B	−179.32 (9)
C7—C1—N1—C5	179.31 (9)	O4B—C9B—C10B—C11B	−178.31 (10)
C2—C1—N1—C6	177.90 (9)	C8B—C9B—C10B—C11B	0.81 (16)
C7—C1—N1—C6	−2.10 (15)	O5B—C10B—C11B—C12B	179.81 (10)
O3A—C8A—C9A—O4A	−1.61 (15)	C9B—C10B—C11B—C12B	−0.33 (17)
C13A—C8A—C9A—O4A	178.86 (10)	C10B—C11B—C12B—C13B	−0.30 (17)
O3A—C8A—C9A—C10A	178.97 (9)	O3B—C8B—C13B—C12B	−179.51 (10)
C13A—C8A—C9A—C10A	−0.56 (15)	C9B—C8B—C13B—C12B	0.05 (17)
O4A—C9A—C10A—O5A	2.79 (15)	C11B—C12B—C13B—C8B	0.44 (17)
C8A—C9A—C10A—O5A	−177.76 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4A^i	0.872 (19)	1.992 (19)	2.8029 (12)	154 (2)
O3A—H2O···O2	0.95 (2)	1.60 (2)	2.5498 (10)	177 (2)
O4A—H3O···O3A^ii	0.872 (19)	1.868 (19)	2.7059 (11)	161 (2)
O5A—H40···O2^iii	0.858 (19)	1.877 (19)	2.6846 (11)	156 (2)
O3B—H5O···O4B	0.89 (2)	2.11 (2)	2.6595 (12)	119 (2)
O4B—H6O···O5A	0.89 (2)	1.94 (2)	2.7249 (11)	146 (2)
O5B—H7O···O3B^iv	0.91 (2)	1.93 (2)	2.8213 (12)	169 (2)
C6—H6C···O2^v	0.98	2.59	3.4416 (14)	145
C13A—H13A···O4B^i	0.95	2.49	3.2642 (13)	139

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

(KA1032_0m_def-pyro_2_4)

Crystal data

C7H9NO2·2(C6H6O3)	Dx = 1.428 Mg m^−3
Mr = 391.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 7479 reflections
a = 14.592 (2) Å	θ = 2.3–30.5°
b = 9.3121 (11) Å	µ = 0.11 mm^−1
c = 26.795 (4) Å	T = 100 K
V = 3640.9 (8) Å^3	Block, colorless
Z = 8	0.32 × 0.28 × 0.18 mm
F(000) = 1648

Data collection

Bruker D8 QUEST PHOTON-100 diffractometer	3817 reflections with I > 2σ(I)
Radiation source: microfocus	Rint = 0.120
ω and φ scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan SADABS, Bruker, 2016	h = −18→18
Tmin = 0.545, Tmax = 0.746	k = −12→12
16757 measured reflections	l = −34→30
6362 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)] = 0.073	w = 1/[σ^2(Fo^2) + (0.0646P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.156	(Δ/σ)max = 0.027
S = 1.05	Δρmax = 0.45 e Å^−3
6362 reflections	Δρmin = −0.40 e Å^−3
565 parameters	Absolute structure: Flack x determined using 732 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
6 restraints	Absolute structure parameter: 0.4 (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
C1A	0.3562 (4)	0.1729 (7)	0.4402 (2)	0.0175 (14)
C2A	0.3562 (4)	0.3219 (7)	0.4453 (2)	0.0139 (13)
C3A	0.4381 (4)	0.4023 (6)	0.44335 (18)	0.0135 (12)
C4A	0.5198 (4)	0.3246 (6)	0.43433 (19)	0.0167 (13)
H4A	0.576537	0.373994	0.431810	0.020*
C5A	0.5171 (4)	0.1782 (7)	0.4292 (2)	0.0197 (13)
H5A	0.572644	0.127773	0.423365	0.024*
C6A	0.4414 (4)	−0.0549 (6)	0.4277 (2)	0.0238 (14)
H6A	0.394029	−0.087117	0.404292	0.036*
H6B	0.430649	−0.098587	0.460449	0.036*
H6C	0.501808	−0.083940	0.415288	0.036*
C7A	0.2707 (4)	0.0865 (7)	0.4426 (2)	0.0238 (16)
H7A	0.254302	0.053989	0.408928	0.036*
H7B	0.220969	0.145466	0.456118	0.036*
H7C	0.280410	0.002903	0.464153	0.036*
O1A	0.2748 (3)	0.3879 (5)	0.45389 (15)	0.0175 (9)
H1O	0.281 (5)	0.477 (3)	0.453 (3)	0.06 (3)*
O2A	0.4347 (2)	0.5415 (4)	0.44946 (13)	0.0150 (9)
N1A	0.4379 (3)	0.1035 (5)	0.43227 (16)	0.0181 (11)
C1B	0.9657 (4)	0.1746 (6)	0.5630 (2)	0.0167 (13)
C2B	0.9659 (4)	0.3197 (6)	0.55825 (19)	0.0148 (12)
C3B	0.8835 (4)	0.4031 (7)	0.55999 (19)	0.0137 (13)
C4B	0.8033 (4)	0.3242 (6)	0.5682 (2)	0.0171 (14)
H4B	0.746618	0.373940	0.570732	0.021*
C5B	0.8036 (4)	0.1810 (6)	0.5725 (2)	0.0176 (14)
H5B	0.747149	0.132030	0.577152	0.021*
C6B	0.8796 (5)	−0.0545 (6)	0.5736 (2)	0.0256 (15)
H6D	0.816281	−0.086581	0.578407	0.038*
H6E	0.917147	−0.086234	0.601857	0.038*
H6F	0.903942	−0.095843	0.542660	0.038*
C7B	1.0513 (4)	0.0890 (6)	0.5606 (2)	0.0220 (14)
H7D	1.042701	0.008030	0.537725	0.033*
H7E	1.066167	0.052628	0.593971	0.033*
H7F	1.101460	0.149728	0.548595	0.033*
O1B	1.0472 (3)	0.3880 (4)	0.54975 (14)	0.0189 (9)
H2O	1.040 (5)	0.475 (3)	0.542 (3)	0.05 (2)*
O2B	0.8875 (2)	0.5416 (4)	0.55430 (14)	0.0165 (9)
N1B	0.8820 (3)	0.1045 (5)	0.57032 (16)	0.0165 (11)
C8A	0.6274 (4)	0.7024 (6)	0.41384 (19)	0.0139 (12)
C9A	0.7118 (4)	0.7707 (6)	0.41431 (19)	0.0135 (12)
C10A	0.7569 (4)	0.7999 (6)	0.3698 (2)	0.0156 (12)
C11A	0.7175 (4)	0.7654 (6)	0.3249 (2)	0.0198 (13)
H11A	0.748141	0.787077	0.294542	0.024*
C12A	0.6330 (5)	0.6987 (7)	0.3242 (2)	0.0230 (14)
H12A	0.605602	0.675173	0.293132	0.028*
C13A	0.5869 (4)	0.6653 (6)	0.3686 (2)	0.0171 (14)
H13A	0.529222	0.618127	0.367821	0.021*
O3A	0.5863 (3)	0.6726 (4)	0.45876 (13)	0.0160 (10)
H3O	0.528 (5)	0.637 (6)	0.453 (2)	0.034 (19)*
O4A	0.7547 (3)	0.8129 (4)	0.45811 (14)	0.0192 (9)
H4O	0.734 (4)	0.757 (6)	0.479 (2)	0.008 (14)*
O5A	0.8423 (3)	0.8623 (4)	0.36995 (15)	0.0193 (9)
H5O	0.862 (8)	0.857 (11)	0.3984 (18)	0.12 (4)*
C8B	0.8484 (4)	1.2642 (7)	0.3106 (2)	0.0215 (15)
C9B	0.9321 (4)	1.1931 (6)	0.3108 (2)	0.0156 (13)
C10B	1.0125 (4)	1.2732 (7)	0.30622 (19)	0.0207 (14)
C11B	1.0107 (4)	1.4222 (7)	0.3010 (2)	0.0248 (14)
H11B	1.065798	1.475824	0.297616	0.030*
C12B	0.9240 (5)	1.4912 (7)	0.3009 (2)	0.0274 (15)
H12B	0.920408	1.592532	0.297330	0.033*
C13B	0.8448 (4)	1.4116 (7)	0.3058 (2)	0.0234 (14)
H13B	0.787149	1.458846	0.305987	0.028*
O3B	0.7728 (3)	1.1758 (5)	0.31597 (16)	0.0253 (10)
H6O	0.728 (5)	1.227 (7)	0.312 (2)	0.018 (19)*
O4B	0.9422 (3)	1.0483 (5)	0.31351 (15)	0.0216 (9)
H7O	0.893 (4)	1.009 (6)	0.326 (2)	0.015 (15)*
O5B	1.0959 (3)	1.2018 (6)	0.30738 (16)	0.0264 (11)
H8O	1.086 (6)	1.111 (9)	0.304 (3)	0.07 (3)*
C8C	0.2995 (4)	1.2728 (7)	0.6946 (2)	0.0210 (14)
C9C	0.3809 (5)	1.1979 (7)	0.6920 (2)	0.0228 (14)
C10C	0.4649 (4)	1.2718 (7)	0.6921 (2)	0.0230 (15)
C11C	0.4649 (5)	1.4215 (7)	0.6961 (2)	0.0298 (16)
H11C	0.520792	1.473729	0.696490	0.036*
C12C	0.3810 (5)	1.4923 (7)	0.6995 (2)	0.0309 (17)
H12C	0.380472	1.593854	0.702884	0.037*
C13C	0.2990 (5)	1.4202 (7)	0.6980 (2)	0.0301 (16)
H13C	0.242728	1.471279	0.699365	0.036*
O3C	0.2189 (3)	1.1958 (6)	0.69358 (16)	0.0300 (11)
H9O	0.227 (5)	1.108 (7)	0.689 (2)	0.03 (2)*
O4C	0.3759 (3)	1.0515 (5)	0.68998 (15)	0.0232 (10)
H10O	0.419 (7)	0.996 (13)	0.687 (6)	0.21 (7)*
O5C	0.5409 (3)	1.1870 (6)	0.68822 (18)	0.0305 (11)
H11O	0.591 (4)	1.226 (10)	0.694 (5)	0.10 (5)*
C8D	0.5652 (4)	0.8007 (6)	0.6347 (2)	0.0146 (12)
C9D	0.6100 (4)	0.7699 (6)	0.58971 (19)	0.0149 (12)
C10D	0.6950 (4)	0.7030 (6)	0.59073 (18)	0.0150 (12)
C11D	0.7356 (4)	0.6676 (6)	0.6363 (2)	0.0185 (13)
H11D	0.793727	0.621581	0.636940	0.022*
C12D	0.6909 (4)	0.7000 (7)	0.6805 (2)	0.0223 (14)
H12D	0.718888	0.676015	0.711409	0.027*
C13D	0.6061 (4)	0.7666 (6)	0.6803 (2)	0.0208 (14)
H13D	0.576139	0.788913	0.710814	0.025*
O3D	0.4804 (3)	0.8635 (4)	0.63489 (15)	0.0203 (9)
H12O	0.460 (5)	0.874 (7)	0.607 (3)	0.04 (2)*
O4D	0.5667 (3)	0.8107 (4)	0.54649 (14)	0.0166 (10)
H13O	0.578 (6)	0.773 (9)	0.516 (4)	0.08 (3)*
O5D	0.7342 (3)	0.6738 (4)	0.54591 (13)	0.0159 (9)
H14O	0.777 (4)	0.618 (6)	0.552 (2)	0.021 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.011 (3)	0.029 (4)	0.013 (3)	−0.002 (3)	−0.003 (2)	0.002 (2)
C2A	0.008 (3)	0.018 (3)	0.016 (3)	0.000 (2)	−0.003 (2)	−0.002 (2)
C3A	0.008 (3)	0.021 (4)	0.011 (3)	−0.003 (2)	−0.002 (2)	0.003 (2)
C4A	0.004 (3)	0.027 (4)	0.019 (3)	0.000 (2)	0.000 (2)	0.000 (2)
C5A	0.010 (3)	0.027 (4)	0.022 (3)	0.007 (3)	0.001 (2)	−0.001 (2)
C6A	0.018 (3)	0.021 (4)	0.032 (3)	0.002 (3)	−0.001 (3)	0.003 (3)
C7A	0.024 (4)	0.020 (4)	0.028 (3)	−0.003 (3)	−0.006 (3)	−0.001 (2)
O1A	0.005 (2)	0.021 (3)	0.026 (2)	0.0038 (17)	0.0013 (17)	0.0012 (18)
O2A	0.007 (2)	0.019 (2)	0.0188 (19)	−0.0025 (16)	0.0010 (16)	−0.0015 (16)
N1A	0.014 (3)	0.022 (3)	0.018 (2)	0.003 (2)	−0.004 (2)	−0.001 (2)
C1B	0.017 (3)	0.019 (3)	0.014 (2)	−0.002 (3)	−0.001 (2)	0.002 (2)
C2B	0.008 (3)	0.021 (3)	0.016 (3)	−0.004 (2)	0.003 (2)	−0.002 (2)
C3B	0.011 (3)	0.023 (4)	0.006 (2)	0.000 (2)	−0.001 (2)	−0.001 (2)
C4B	0.014 (3)	0.020 (3)	0.017 (3)	0.000 (3)	0.000 (2)	0.001 (2)
C5B	0.005 (3)	0.030 (4)	0.018 (3)	−0.004 (3)	0.000 (2)	−0.002 (2)
C6B	0.032 (4)	0.023 (4)	0.022 (3)	−0.004 (3)	0.003 (3)	0.006 (2)
C7B	0.018 (3)	0.020 (3)	0.028 (3)	0.007 (3)	−0.004 (3)	−0.001 (2)
O1B	0.010 (2)	0.019 (3)	0.028 (2)	0.0020 (18)	0.0010 (18)	0.0034 (18)
O2B	0.011 (2)	0.020 (2)	0.0190 (19)	0.0001 (16)	0.0005 (16)	0.0024 (16)
N1B	0.019 (3)	0.014 (3)	0.016 (2)	−0.003 (2)	0.003 (2)	−0.0003 (19)
C8A	0.014 (3)	0.016 (3)	0.012 (2)	0.007 (2)	0.001 (2)	−0.001 (2)
C9A	0.011 (3)	0.016 (3)	0.014 (2)	0.005 (2)	−0.003 (2)	−0.001 (2)
C10A	0.013 (3)	0.016 (3)	0.018 (2)	0.000 (2)	0.001 (2)	0.000 (2)
C11A	0.013 (3)	0.030 (4)	0.016 (3)	0.004 (3)	0.002 (2)	0.000 (2)
C12A	0.024 (4)	0.032 (4)	0.013 (2)	−0.001 (3)	−0.003 (3)	−0.002 (2)
C13A	0.014 (3)	0.021 (4)	0.016 (3)	−0.005 (2)	−0.005 (2)	0.003 (2)
O3A	0.008 (2)	0.028 (3)	0.0119 (19)	−0.0073 (18)	0.0001 (16)	0.0002 (16)
O4A	0.023 (2)	0.022 (2)	0.0135 (18)	−0.0093 (19)	−0.0016 (17)	0.0030 (16)
O5A	0.011 (2)	0.028 (3)	0.0185 (19)	−0.0055 (17)	−0.0016 (18)	0.0036 (17)
C8B	0.016 (4)	0.035 (4)	0.014 (3)	−0.003 (3)	0.000 (3)	0.002 (3)
C9B	0.009 (3)	0.022 (4)	0.016 (3)	−0.003 (2)	−0.002 (2)	0.003 (2)
C10B	0.017 (3)	0.033 (4)	0.012 (3)	0.003 (3)	0.001 (2)	0.002 (2)
C11B	0.021 (4)	0.033 (4)	0.021 (3)	−0.012 (3)	0.003 (3)	0.001 (2)
C12B	0.039 (4)	0.025 (4)	0.018 (3)	0.004 (3)	0.000 (3)	0.002 (2)
C13B	0.016 (4)	0.033 (4)	0.021 (3)	0.007 (3)	−0.001 (3)	0.000 (3)
O3B	0.010 (2)	0.033 (3)	0.033 (2)	0.004 (2)	−0.002 (2)	0.0063 (19)
O4B	0.013 (2)	0.024 (3)	0.027 (2)	−0.0012 (19)	0.0041 (19)	0.0032 (19)
O5B	0.011 (3)	0.035 (3)	0.033 (3)	−0.003 (2)	0.001 (2)	0.000 (2)
C8C	0.020 (4)	0.027 (4)	0.016 (3)	0.002 (3)	0.001 (3)	−0.004 (2)
C9C	0.029 (4)	0.026 (4)	0.013 (3)	0.000 (3)	0.002 (3)	−0.004 (2)
C10C	0.019 (4)	0.032 (4)	0.018 (3)	−0.003 (3)	0.001 (3)	−0.002 (3)
C11C	0.043 (5)	0.030 (4)	0.017 (3)	−0.013 (3)	0.004 (3)	−0.004 (3)
C12C	0.050 (5)	0.023 (4)	0.019 (3)	0.004 (3)	0.002 (3)	0.002 (2)
C13C	0.029 (4)	0.044 (5)	0.018 (3)	0.010 (3)	0.005 (3)	−0.003 (3)
O3C	0.018 (3)	0.040 (3)	0.032 (2)	0.010 (2)	0.001 (2)	−0.005 (2)
O4C	0.015 (2)	0.029 (3)	0.026 (2)	−0.002 (2)	−0.0021 (19)	−0.0085 (19)
O5C	0.010 (3)	0.042 (3)	0.039 (3)	−0.001 (2)	0.000 (2)	0.002 (2)
C8D	0.012 (3)	0.017 (3)	0.015 (2)	−0.001 (3)	0.004 (2)	0.000 (2)
C9D	0.013 (3)	0.015 (3)	0.017 (3)	−0.003 (2)	−0.002 (2)	0.002 (2)
C10D	0.012 (3)	0.019 (3)	0.014 (2)	−0.006 (2)	0.003 (2)	−0.002 (2)
C11D	0.011 (3)	0.027 (4)	0.018 (3)	0.001 (2)	0.004 (2)	0.002 (2)
C12D	0.018 (3)	0.036 (4)	0.013 (2)	0.004 (3)	−0.001 (2)	0.001 (2)
C13D	0.021 (4)	0.030 (4)	0.011 (2)	−0.002 (3)	0.004 (2)	−0.001 (2)
O3D	0.009 (2)	0.035 (3)	0.0162 (18)	0.0058 (18)	−0.0005 (18)	−0.0007 (17)
O4D	0.012 (2)	0.024 (2)	0.0137 (19)	0.0073 (18)	−0.0024 (17)	−0.0018 (16)
O5D	0.010 (2)	0.024 (3)	0.0144 (18)	0.0050 (18)	0.0027 (17)	0.0015 (16)

Geometric parameters (Å, º)

C1A—N1A	1.373 (8)	C13A—H13A	0.9500
C1A—C2A	1.395 (9)	O3A—H3O	0.93 (7)
C1A—C7A	1.486 (8)	O4A—H4O	0.82 (5)
C2A—O1A	1.357 (7)	O5A—H5O	0.82 (3)
C2A—C3A	1.411 (8)	C8B—C13B	1.379 (9)
C3A—O2A	1.308 (7)	C8B—O3B	1.383 (7)
C3A—C4A	1.414 (8)	C8B—C9B	1.389 (9)
C4A—C5A	1.370 (9)	C9B—O4B	1.358 (7)
C4A—H4A	0.9500	C9B—C10B	1.396 (9)
C5A—N1A	1.352 (8)	C10B—O5B	1.388 (8)
C5A—H5A	0.9500	C10B—C11B	1.395 (8)
C6A—N1A	1.481 (8)	C11B—C12B	1.420 (9)
C6A—H6A	0.9800	C11B—H11B	0.9500
C6A—H6B	0.9800	C12B—C13B	1.378 (9)
C6A—H6C	0.9800	C12B—H12B	0.9500
C7A—H7A	0.9800	C13B—H13B	0.9500
C7A—H7B	0.9800	O3B—H6O	0.82 (7)
C7A—H7C	0.9800	O4B—H7O	0.87 (6)
O1A—H1O	0.84 (3)	O5B—H8O	0.86 (9)
C1B—C2B	1.357 (8)	C8C—C13C	1.375 (9)
C1B—N1B	1.399 (8)	C8C—O3C	1.377 (8)
C1B—C7B	1.483 (8)	C8C—C9C	1.379 (10)
C2B—O1B	1.365 (7)	C9C—O4C	1.366 (8)
C2B—C3B	1.432 (8)	C9C—C10C	1.406 (9)
C3B—O2B	1.300 (7)	C10C—O5C	1.366 (8)
C3B—C4B	1.400 (9)	C10C—C11C	1.398 (9)
C4B—C5B	1.338 (8)	C11C—C12C	1.394 (10)
C4B—H4B	0.9500	C11C—H11C	0.9500
C5B—N1B	1.349 (8)	C12C—C13C	1.372 (10)
C5B—H5B	0.9500	C12C—H12C	0.9500
C6B—N1B	1.484 (8)	C13C—H13C	0.9500
C6B—H6D	0.9800	O3C—H9O	0.83 (7)
C6B—H6E	0.9800	O4C—H10O	0.82 (3)
C6B—H6F	0.9800	O5C—H11O	0.84 (3)
C7B—H7D	0.9800	C8D—O3D	1.369 (7)
C7B—H7E	0.9800	C8D—C13D	1.397 (8)
C7B—H7F	0.9800	C8D—C9D	1.401 (8)
O1B—H2O	0.84 (3)	C9D—O4D	1.373 (6)
C8A—O3A	1.373 (6)	C9D—C10D	1.388 (8)
C8A—C9A	1.386 (8)	C10D—O5D	1.358 (6)
C8A—C13A	1.392 (8)	C10D—C11D	1.396 (8)
C9A—O4A	1.387 (6)	C11D—C12D	1.386 (8)
C9A—C10A	1.390 (8)	C11D—H11D	0.9500
C10A—C11A	1.371 (8)	C12D—C13D	1.384 (9)
C10A—O5A	1.375 (7)	C12D—H12D	0.9500
C11A—C12A	1.381 (9)	C13D—H13D	0.9500
C11A—H11A	0.9500	O3D—H12O	0.82 (7)
C12A—C13A	1.400 (8)	O4D—H13O	0.91 (9)
C12A—H12A	0.9500	O5D—H14O	0.83 (6)
N1A—C1A—C2A	118.9 (6)	C12A—C11A—H11A	120.3
N1A—C1A—C7A	118.7 (6)	C11A—C12A—C13A	121.2 (5)
C2A—C1A—C7A	122.4 (6)	C11A—C12A—H12A	119.4
O1A—C2A—C1A	117.8 (5)	C13A—C12A—H12A	119.4
O1A—C2A—C3A	120.5 (5)	C8A—C13A—C12A	118.7 (5)
C1A—C2A—C3A	121.6 (6)	C8A—C13A—H13A	120.7
O2A—C3A—C2A	119.2 (5)	C12A—C13A—H13A	120.7
O2A—C3A—C4A	124.1 (5)	C8A—O3A—H3O	110 (4)
C2A—C3A—C4A	116.7 (6)	C9A—O4A—H4O	103 (4)
C5A—C4A—C3A	120.1 (5)	C10A—O5A—H5O	107 (8)
C5A—C4A—H4A	119.9	C13B—C8B—O3B	124.9 (6)
C3A—C4A—H4A	119.9	C13B—C8B—C9B	120.5 (6)
N1A—C5A—C4A	122.1 (6)	O3B—C8B—C9B	114.6 (6)
N1A—C5A—H5A	119.0	O4B—C9B—C8B	124.7 (6)
C4A—C5A—H5A	119.0	O4B—C9B—C10B	116.4 (5)
N1A—C6A—H6A	109.5	C8B—C9B—C10B	118.9 (6)
N1A—C6A—H6B	109.5	O5B—C10B—C9B	118.7 (6)
H6A—C6A—H6B	109.5	O5B—C10B—C11B	119.6 (6)
N1A—C6A—H6C	109.5	C9B—C10B—C11B	121.7 (6)
H6A—C6A—H6C	109.5	C10B—C11B—C12B	117.8 (6)
H6B—C6A—H6C	109.5	C10B—C11B—H11B	121.1
C1A—C7A—H7A	109.5	C12B—C11B—H11B	121.1
C1A—C7A—H7B	109.5	C13B—C12B—C11B	120.2 (6)
H7A—C7A—H7B	109.5	C13B—C12B—H12B	119.9
C1A—C7A—H7C	109.5	C11B—C12B—H12B	119.9
H7A—C7A—H7C	109.5	C12B—C13B—C8B	120.9 (6)
H7B—C7A—H7C	109.5	C12B—C13B—H13B	119.6
C2A—O1A—H1O	111 (6)	C8B—C13B—H13B	119.6
C5A—N1A—C1A	120.6 (5)	C8B—O3B—H6O	106 (5)
C5A—N1A—C6A	118.6 (5)	C9B—O4B—H7O	110 (4)
C1A—N1A—C6A	120.8 (5)	C10B—O5B—H8O	108 (6)
C2B—C1B—N1B	118.7 (5)	C13C—C8C—O3C	121.1 (6)
C2B—C1B—C7B	121.9 (6)	C13C—C8C—C9C	120.8 (6)
N1B—C1B—C7B	119.3 (5)	O3C—C8C—C9C	118.1 (6)
C1B—C2B—O1B	118.8 (5)	O4C—C9C—C8C	117.4 (6)
C1B—C2B—C3B	122.3 (6)	O4C—C9C—C10C	122.4 (6)
O1B—C2B—C3B	118.8 (5)	C8C—C9C—C10C	120.2 (6)
O2B—C3B—C4B	125.2 (6)	O5C—C10C—C11C	125.6 (6)
O2B—C3B—C2B	119.8 (5)	O5C—C10C—C9C	115.1 (6)
C4B—C3B—C2B	115.0 (6)	C11C—C10C—C9C	119.2 (6)
C5B—C4B—C3B	122.2 (6)	C12C—C11C—C10C	118.5 (6)
C5B—C4B—H4B	118.9	C12C—C11C—H11C	120.8
C3B—C4B—H4B	118.9	C10C—C11C—H11C	120.8
C4B—C5B—N1B	121.7 (6)	C13C—C12C—C11C	122.1 (6)
C4B—C5B—H5B	119.1	C13C—C12C—H12C	118.9
N1B—C5B—H5B	119.1	C11C—C12C—H12C	118.9
N1B—C6B—H6D	109.5	C12C—C13C—C8C	119.1 (6)
N1B—C6B—H6E	109.5	C12C—C13C—H13C	120.5
H6D—C6B—H6E	109.5	C8C—C13C—H13C	120.5
N1B—C6B—H6F	109.5	C8C—O3C—H9O	113 (5)
H6D—C6B—H6F	109.5	C9C—O4C—H10O	127 (10)
H6E—C6B—H6F	109.5	C10C—O5C—H11O	117 (7)
C1B—C7B—H7D	109.5	O3D—C8D—C13D	118.7 (5)
C1B—C7B—H7E	109.5	O3D—C8D—C9D	120.8 (5)
H7D—C7B—H7E	109.5	C13D—C8D—C9D	120.5 (5)
C1B—C7B—H7F	109.5	O4D—C9D—C10D	123.5 (5)
H7D—C7B—H7F	109.5	O4D—C9D—C8D	117.0 (5)
H7E—C7B—H7F	109.5	C10D—C9D—C8D	119.5 (5)
C2B—O1B—H2O	112 (5)	O5D—C10D—C9D	116.7 (5)
C5B—N1B—C1B	120.0 (5)	O5D—C10D—C11D	123.1 (5)
C5B—N1B—C6B	120.4 (5)	C9D—C10D—C11D	120.2 (5)
C1B—N1B—C6B	119.6 (5)	C12D—C11D—C10D	119.7 (5)
O3A—C8A—C9A	118.2 (5)	C12D—C11D—H11D	120.1
O3A—C8A—C13A	121.9 (5)	C10D—C11D—H11D	120.1
C9A—C8A—C13A	119.9 (5)	C13D—C12D—C11D	121.0 (5)
C8A—C9A—O4A	122.6 (5)	C13D—C12D—H12D	119.5
C8A—C9A—C10A	120.2 (5)	C11D—C12D—H12D	119.5
O4A—C9A—C10A	117.3 (5)	C12D—C13D—C8D	119.1 (5)
C11A—C10A—O5A	118.8 (5)	C12D—C13D—H13D	120.4
C11A—C10A—C9A	120.6 (5)	C8D—C13D—H13D	120.4
O5A—C10A—C9A	120.6 (5)	C8D—O3D—H12O	112 (5)
C10A—C11A—C12A	119.4 (5)	C9D—O4D—H13O	125 (6)
C10A—C11A—H11A	120.3	C10D—O5D—H14O	106 (4)
N1A—C1A—C2A—O1A	−179.1 (5)	O3A—C8A—C13A—C12A	−179.8 (5)
C7A—C1A—C2A—O1A	1.6 (8)	C9A—C8A—C13A—C12A	−0.2 (8)
N1A—C1A—C2A—C3A	−1.0 (8)	C11A—C12A—C13A—C8A	0.9 (9)
C7A—C1A—C2A—C3A	179.6 (5)	C13B—C8B—C9B—O4B	−177.5 (5)
O1A—C2A—C3A—O2A	−0.5 (8)	O3B—C8B—C9B—O4B	3.2 (8)
C1A—C2A—C3A—O2A	−178.5 (5)	C13B—C8B—C9B—C10B	0.1 (9)
O1A—C2A—C3A—C4A	179.9 (5)	O3B—C8B—C9B—C10B	−179.2 (5)
C1A—C2A—C3A—C4A	1.9 (7)	O4B—C9B—C10B—O5B	−3.4 (7)
O2A—C3A—C4A—C5A	178.9 (5)	C8B—C9B—C10B—O5B	178.9 (5)
C2A—C3A—C4A—C5A	−1.6 (7)	O4B—C9B—C10B—C11B	177.2 (5)
C3A—C4A—C5A—N1A	0.3 (8)	C8B—C9B—C10B—C11B	−0.6 (9)
C4A—C5A—N1A—C1A	0.6 (8)	O5B—C10B—C11B—C12B	−178.9 (5)
C4A—C5A—N1A—C6A	−178.4 (5)	C9B—C10B—C11B—C12B	0.5 (8)
C2A—C1A—N1A—C5A	−0.3 (8)	C10B—C11B—C12B—C13B	0.1 (9)
C7A—C1A—N1A—C5A	179.1 (5)	C11B—C12B—C13B—C8B	−0.5 (9)
C2A—C1A—N1A—C6A	178.7 (5)	O3B—C8B—C13B—C12B	179.7 (5)
C7A—C1A—N1A—C6A	−1.9 (7)	C9B—C8B—C13B—C12B	0.5 (9)
N1B—C1B—C2B—O1B	−178.2 (4)	C13C—C8C—C9C—O4C	178.4 (5)
C7B—C1B—C2B—O1B	1.7 (8)	O3C—C8C—C9C—O4C	−1.7 (8)
N1B—C1B—C2B—C3B	−0.6 (8)	C13C—C8C—C9C—C10C	−0.9 (9)
C7B—C1B—C2B—C3B	179.3 (5)	O3C—C8C—C9C—C10C	179.0 (5)
C1B—C2B—C3B—O2B	−178.7 (5)	O4C—C9C—C10C—O5C	2.3 (9)
O1B—C2B—C3B—O2B	−1.1 (7)	C8C—C9C—C10C—O5C	−178.5 (5)
C1B—C2B—C3B—C4B	1.5 (8)	O4C—C9C—C10C—C11C	−177.7 (5)
O1B—C2B—C3B—C4B	179.1 (4)	C8C—C9C—C10C—C11C	1.5 (9)
O2B—C3B—C4B—C5B	178.3 (5)	O5C—C10C—C11C—C12C	179.6 (6)
C2B—C3B—C4B—C5B	−2.0 (8)	C9C—C10C—C11C—C12C	−0.4 (9)
C3B—C4B—C5B—N1B	1.6 (9)	C10C—C11C—C12C—C13C	−1.3 (9)
C4B—C5B—N1B—C1B	−0.5 (8)	C11C—C12C—C13C—C8C	1.9 (9)
C4B—C5B—N1B—C6B	−178.0 (5)	O3C—C8C—C13C—C12C	179.3 (5)
C2B—C1B—N1B—C5B	0.1 (8)	C9C—C8C—C13C—C12C	−0.8 (9)
C7B—C1B—N1B—C5B	−179.9 (5)	O3D—C8D—C9D—O4D	2.6 (8)
C2B—C1B—N1B—C6B	177.6 (5)	C13D—C8D—C9D—O4D	−178.0 (5)
C7B—C1B—N1B—C6B	−2.4 (7)	O3D—C8D—C9D—C10D	−178.4 (5)
O3A—C8A—C9A—O4A	−1.7 (8)	C13D—C8D—C9D—C10D	1.0 (8)
C13A—C8A—C9A—O4A	178.7 (5)	O4D—C9D—C10D—O5D	−2.1 (8)
O3A—C8A—C9A—C10A	178.5 (5)	C8D—C9D—C10D—O5D	178.9 (5)
C13A—C8A—C9A—C10A	−1.1 (9)	O4D—C9D—C10D—C11D	178.5 (5)
C8A—C9A—C10A—C11A	1.8 (8)	C8D—C9D—C10D—C11D	−0.5 (8)
O4A—C9A—C10A—C11A	−178.0 (5)	O5D—C10D—C11D—C12D	−179.5 (6)
C8A—C9A—C10A—O5A	−177.3 (5)	C9D—C10D—C11D—C12D	−0.2 (8)
O4A—C9A—C10A—O5A	2.9 (8)	C10D—C11D—C12D—C13D	0.2 (9)
O5A—C10A—C11A—C12A	178.0 (5)	C11D—C12D—C13D—C8D	0.4 (10)
C9A—C10A—C11A—C12A	−1.1 (9)	O3D—C8D—C13D—C12D	178.4 (6)
C10A—C11A—C12A—C13A	−0.3 (9)	C9D—C8D—C13D—C12D	−1.0 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O···O4A^i	0.84 (3)	2.00 (4)	2.804 (6)	162 (8)
O1B—H2O···O4D^ii	0.84 (3)	2.04 (4)	2.821 (6)	155 (7)
O3A—H3O···O2A	0.93 (7)	1.63 (7)	2.539 (5)	167 (6)
O4A—H4O···O3A	0.82 (5)	2.35 (6)	2.782 (6)	114 (4)
O4A—H4O···O5D	0.82 (5)	1.96 (5)	2.702 (5)	151 (5)
O5A—H5O···O2A^ii	0.82 (3)	1.97 (7)	2.676 (5)	144 (10)
O5A—H5O···O4A	0.82 (3)	2.28 (11)	2.726 (6)	115 (10)
O3B—H6O···O5B^iii	0.82 (7)	2.04 (7)	2.831 (7)	163 (6)
O4B—H7O···O5A	0.87 (6)	1.95 (6)	2.722 (6)	146 (5)
O5B—H8O···O4B	0.86 (9)	2.19 (9)	2.666 (6)	114 (7)
O3C—H9O···O4C	0.83 (7)	2.24 (7)	2.657 (7)	111 (6)
O4C—H10O···O3D	0.82 (3)	2.06 (11)	2.752 (6)	142 (15)
O5C—H11O···O3C^iv	0.84 (3)	2.00 (4)	2.821 (7)	169 (12)
O3D—H12O···O2B^i	0.82 (7)	1.92 (7)	2.698 (6)	157 (7)
O3D—H12O···O4D	0.82 (7)	2.32 (7)	2.727 (6)	112 (6)
O4D—H13O···O3A	0.91 (9)	1.80 (9)	2.695 (5)	170 (9)
O5D—H14O···O2B	0.83 (6)	1.76 (6)	2.564 (5)	163 (6)
C13A—H13A···O4B^i	0.95	2.48	3.255 (7)	139
C6B—H6F···O2A^v	0.98	2.59	3.424 (7)	143
C11D—H11D···O4C^ii	0.95	2.46	3.228 (7)	138

Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x+1/2, −y+3/2, z; (iii) x−1/2, −y+5/2, z; (iv) x+1/2, −y+5/2, z; (v) x+1/2, −y+1/2, z.