Crystal engineering: co-crystals of cinnamic acid derivatives with a pyridyl derivative co-crystallizer

A number of hydrogen-bonded co-crystals, consisting of a cinnamic acid derivative and a pyridyl co-crystallizer, have been synthesized and their properties investigated by X-ray diffraction. Samples were prepared by recrystallization or solvent drop grinding of trans-cinnamic acid (1), 4-methylcinnamic acid (2), 4-methoxy cinnamic acid (3) or 3,4-methoxy cinnamic acid (4), with 4,4-dipyridyl (A), iso-nicotinamide (B) or nicotinamide (C). The X-ray single-crystal structures of seven novel co-crystals, obtained through recrystallization, are examined and the hydrogen-bonding interactions discussed. Consistent hydrogen-bonding motifs were observed for samples prepared when using 4,4-dipyridyl (A) or iso-nicotinamide (B) as the co-crystallizing agent. Powder X-ray diffraction analysis of the samples prepared by solvent drop grinding suggests the formation of ten co-crystals.

Computing details

For all compounds, cell refinement: SAINT v8.34A (Bruker, 2013); data reduction: SAINT v8.34A (Bruker, 2013); program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Figures

(1A)

Crystal data

C10H8N2·2(C9H8O2)	F(000) = 476
Mr = 452.49	Dx = 1.297 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7952 (2) Å	Cell parameters from 4090 reflections
b = 7.1669 (2) Å	θ = 2.7–27.9°
c = 20.7708 (5) Å	µ = 0.09 mm^−1
β = 93.2075 (17)°	T = 100 K
V = 1158.59 (5) Å^3	Block, colourless
Z = 2	0.63 × 0.32 × 0.3 mm

Data collection

Bruker Apex II kappa CCD area detector diffractometer	2759 independent reflections
Radiation source: fine-focus sealed tube	2356 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0483 before and 0.0369 after correction. The Ratio of minimum to maximum transmission is 0.8822. The λ/2 correction factor is 0.00150.	h = −10→10
Tmin = 0.658, Tmax = 0.746	k = −9→6
10075 measured reflections	l = −26→27

Refinement

Refinement on F^2	Primary atom site location: iterative
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) = 0.095	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 0.3171P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2759 reflections	Δρmax = 0.38 e Å^−3
158 parameters	Δρmin = −0.20 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
N1	0.85950 (11)	−0.06496 (12)	0.43380 (4)	0.0190 (2)
C10	0.78266 (14)	−0.14219 (15)	0.48298 (5)	0.0206 (2)
H10	0.6889	−0.0782	0.5002	0.025*
C11	0.83323 (14)	−0.31159 (15)	0.51017 (5)	0.0205 (2)
H11	0.7738	−0.3616	0.5449	0.025*
C12	0.97121 (13)	−0.40820 (13)	0.48642 (5)	0.0158 (2)
C13	1.05195 (14)	−0.32545 (15)	0.43549 (5)	0.0200 (2)
H13	1.1478	−0.3844	0.4178	0.024*
C14	0.99190 (14)	−0.15702 (15)	0.41076 (5)	0.0213 (2)
H14	1.0477	−0.1041	0.3756	0.026*
C1	0.42927 (14)	0.88599 (15)	0.35401 (5)	0.0219 (2)
H1	0.4102	0.8584	0.3978	0.026*
C2	0.36694 (15)	1.05107 (16)	0.32678 (6)	0.0271 (3)
H2	0.3045	1.1353	0.3519	0.032*
C3	0.39507 (16)	1.09418 (18)	0.26306 (6)	0.0314 (3)
H3	0.3514	1.2070	0.2445	0.038*
C4	0.48690 (16)	0.9720 (2)	0.22674 (6)	0.0336 (3)
H4	0.5074	1.0014	0.1832	0.040*
C5	0.54941 (15)	0.80600 (18)	0.25361 (6)	0.0266 (3)
H5	0.6128	0.7230	0.2283	0.032*
O1	0.75081 (10)	0.25795 (11)	0.38655 (4)	0.02112 (19)
O2	0.59216 (10)	0.25714 (10)	0.47309 (4)	0.02226 (19)
C6	0.52001 (13)	0.76003 (15)	0.31739 (5)	0.0192 (2)
C7	0.58684 (14)	0.58166 (15)	0.34294 (5)	0.0192 (2)
H7	0.6539	0.5095	0.3153	0.023*
C8	0.56258 (13)	0.51123 (14)	0.40105 (5)	0.0179 (2)
H8	0.4953	0.5803	0.4294	0.022*
C9	0.63538 (13)	0.33073 (14)	0.42350 (5)	0.0171 (2)
H1A	0.790 (2)	0.141 (3)	0.4041 (8)	0.054 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0187 (4)	0.0167 (4)	0.0213 (4)	0.0017 (3)	−0.0003 (4)	−0.0013 (3)
C10	0.0193 (5)	0.0174 (5)	0.0255 (5)	0.0031 (4)	0.0042 (4)	−0.0021 (4)
C11	0.0205 (5)	0.0173 (5)	0.0240 (5)	0.0015 (4)	0.0053 (4)	0.0006 (4)
C12	0.0152 (5)	0.0148 (5)	0.0170 (5)	0.0001 (4)	−0.0024 (4)	−0.0034 (4)
C13	0.0194 (5)	0.0208 (5)	0.0199 (5)	0.0048 (4)	0.0022 (4)	−0.0015 (4)
C14	0.0227 (5)	0.0215 (5)	0.0199 (5)	0.0023 (4)	0.0041 (4)	0.0019 (4)
C1	0.0220 (5)	0.0217 (5)	0.0219 (5)	0.0001 (4)	0.0007 (4)	0.0029 (4)
C2	0.0238 (6)	0.0218 (6)	0.0354 (6)	0.0027 (4)	0.0001 (5)	0.0032 (5)
C3	0.0231 (6)	0.0287 (6)	0.0420 (7)	0.0025 (5)	−0.0020 (5)	0.0171 (5)
C4	0.0272 (6)	0.0439 (7)	0.0299 (6)	0.0037 (5)	0.0037 (5)	0.0193 (6)
C5	0.0222 (6)	0.0345 (6)	0.0236 (6)	0.0042 (5)	0.0047 (4)	0.0071 (5)
O1	0.0243 (4)	0.0193 (4)	0.0204 (4)	0.0069 (3)	0.0076 (3)	0.0034 (3)
O2	0.0261 (4)	0.0205 (4)	0.0209 (4)	0.0038 (3)	0.0073 (3)	0.0038 (3)
C6	0.0163 (5)	0.0211 (5)	0.0201 (5)	−0.0005 (4)	−0.0004 (4)	0.0040 (4)
C7	0.0179 (5)	0.0204 (5)	0.0192 (5)	0.0022 (4)	0.0019 (4)	−0.0006 (4)
C8	0.0170 (5)	0.0172 (5)	0.0198 (5)	0.0020 (4)	0.0030 (4)	−0.0009 (4)
C9	0.0167 (5)	0.0169 (5)	0.0176 (5)	−0.0002 (4)	0.0013 (4)	−0.0010 (4)

Geometric parameters (Å, º)

N1—C10	1.3332 (14)	C2—C3	1.3885 (17)
N1—C14	1.3359 (14)	C3—H3	0.9500
C10—H10	0.9500	C3—C4	1.3818 (19)
C10—C11	1.3868 (15)	C4—H4	0.9500
C11—H11	0.9500	C4—C5	1.3903 (17)
C11—C12	1.3925 (14)	C5—H5	0.9500
C12—C12^i	1.4909 (19)	C5—C6	1.3965 (15)
C12—C13	1.3933 (14)	O1—C9	1.3220 (12)
C13—H13	0.9500	O1—H1A	0.956 (19)
C13—C14	1.3832 (15)	O2—C9	1.2214 (12)
C14—H14	0.9500	C6—C7	1.4684 (14)
C1—H1	0.9500	C7—H7	0.9500
C1—C2	1.3875 (15)	C7—C8	1.3316 (15)
C1—C6	1.3979 (15)	C8—H8	0.9500
C2—H2	0.9500	C8—C9	1.4776 (14)
C10—N1—C14	117.30 (9)	C2—C3—H3	120.2
N1—C10—H10	118.5	C4—C3—C2	119.57 (11)
N1—C10—C11	123.08 (9)	C4—C3—H3	120.2
C11—C10—H10	118.5	C3—C4—H4	119.9
C10—C11—H11	120.0	C3—C4—C5	120.26 (11)
C10—C11—C12	119.92 (10)	C5—C4—H4	119.9
C12—C11—H11	120.0	C4—C5—H5	119.7
C11—C12—C12^i	121.80 (11)	C4—C5—C6	120.68 (11)
C11—C12—C13	116.61 (9)	C6—C5—H5	119.7
C13—C12—C12^i	121.59 (11)	C9—O1—H1A	109.7 (10)
C12—C13—H13	120.1	C1—C6—C7	123.07 (9)
C14—C13—C12	119.70 (9)	C5—C6—C1	118.60 (10)
C14—C13—H13	120.1	C5—C6—C7	118.32 (10)
N1—C14—C13	123.38 (10)	C6—C7—H7	116.8
N1—C14—H14	118.3	C8—C7—C6	126.30 (10)
C13—C14—H14	118.3	C8—C7—H7	116.8
C2—C1—H1	119.8	C7—C8—H8	118.4
C2—C1—C6	120.35 (10)	C7—C8—C9	123.11 (9)
C6—C1—H1	119.8	C9—C8—H8	118.4
C1—C2—H2	119.7	O1—C9—C8	115.10 (9)
C1—C2—C3	120.53 (11)	O2—C9—O1	123.23 (9)
C3—C2—H2	119.7	O2—C9—C8	121.66 (9)
N1—C10—C11—C12	0.57 (17)	C2—C1—C6—C7	−178.95 (10)
C10—N1—C14—C13	−0.28 (17)	C2—C3—C4—C5	0.6 (2)
C10—C11—C12—C12^i	−179.25 (11)	C3—C4—C5—C6	0.2 (2)
C10—C11—C12—C13	0.16 (16)	C4—C5—C6—C1	−1.21 (18)
C11—C12—C13—C14	−0.90 (15)	C4—C5—C6—C7	179.10 (11)
C12^i—C12—C13—C14	178.52 (11)	C5—C6—C7—C8	−175.98 (11)
C12—C13—C14—N1	1.01 (17)	C6—C1—C2—C3	−0.57 (18)
C14—N1—C10—C11	−0.51 (16)	C6—C7—C8—C9	−179.54 (10)
C1—C2—C3—C4	−0.43 (19)	C7—C8—C9—O1	11.16 (15)
C1—C6—C7—C8	4.35 (18)	C7—C8—C9—O2	−169.67 (11)
C2—C1—C6—C5	1.38 (17)

Symmetry code: (i) −x+2, −y−1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.956 (19)	1.679 (19)	2.6350 (12)	179.1 (16)

(1B)

Crystal data

C9H8O2·C6H6N2O	Z = 4
Mr = 270.28	F(000) = 568
Triclinic, P1	Dx = 1.388 Mg m^−3
a = 8.4176 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6487 (4) Å	Cell parameters from 4776 reflections
c = 15.0679 (5) Å	θ = 2.7–27.9°
α = 75.883 (2)°	µ = 0.10 mm^−1
β = 82.329 (2)°	T = 100 K
γ = 83.301 (2)°	Block, colourless
V = 1293.14 (8) Å^3	0.6 × 0.47 × 0.33 mm

Data collection

Bruker Apex II kappa CCDC area detector diffractometer	6048 independent reflections
Radiation source: fine-focus sealed tube	4955 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 28.0°, θmin = 1.4°
Absorption correction: multi-scan SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0528 before and 0.0297 after correction. The Ratio of minimum to maximum transmission is 0.8372. The λ/2 correction factor is 0.00150.	h = −11→11
Tmin = 0.624, Tmax = 0.746	k = −14→14
11995 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0643P)^2 + 0.2177P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6048 reflections	Δρmax = 0.46 e Å^−3
385 parameters	Δρmin = −0.24 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O4	0.20081 (11)	1.06934 (8)	0.04949 (6)	0.0209 (2)
O5	0.06173 (10)	1.06118 (8)	0.18708 (6)	0.0210 (2)
C16	−0.22091 (14)	1.45975 (11)	−0.03760 (8)	0.0155 (2)
H16	−0.2668	1.4178	0.0218	0.019*
C17	−0.30257 (14)	1.56850 (11)	−0.08840 (8)	0.0170 (2)
H17	−0.4054	1.5999	−0.0641	0.020*
C18	−0.23506 (15)	1.63185 (11)	−0.17466 (8)	0.0174 (2)
H18	−0.2920	1.7060	−0.2092	0.021*
C19	−0.08525 (15)	1.58713 (11)	−0.21032 (8)	0.0172 (2)
H19	−0.0379	1.6317	−0.2686	0.021*
C20	−0.00428 (14)	1.47674 (11)	−0.16057 (8)	0.0157 (2)
H20	0.0976	1.4450	−0.1858	0.019*
C21	−0.07068 (14)	1.41180 (11)	−0.07389 (7)	0.0138 (2)
C22	0.01927 (14)	1.29479 (11)	−0.02491 (8)	0.0148 (2)
H22	0.1082	1.2593	−0.0596	0.018*
C23	−0.01026 (14)	1.23305 (11)	0.06287 (8)	0.0154 (2)
H23	−0.0975	1.2667	0.0997	0.019*
C24	0.08690 (14)	1.11434 (11)	0.10544 (8)	0.0150 (2)
O1	1.10340 (11)	−0.49228 (9)	0.60009 (6)	0.0221 (2)
O2	1.28718 (11)	−0.45971 (8)	0.47706 (6)	0.0204 (2)
C1	1.48226 (14)	−0.91144 (11)	0.68608 (8)	0.0168 (2)
H1A	1.5339	−0.8720	0.6276	0.020*
C2	1.55067 (15)	−1.02660 (12)	0.73728 (8)	0.0200 (3)
H2	1.6496	−1.0654	0.7138	0.024*
C3	1.47557 (16)	−1.08570 (12)	0.82277 (8)	0.0203 (3)
H3	1.5236	−1.1643	0.8576	0.024*
C4	1.33081 (15)	−1.02993 (11)	0.85702 (8)	0.0186 (2)
H4A	1.2789	−1.0703	0.9152	0.022*
C5	1.26186 (15)	−0.91475 (11)	0.80596 (8)	0.0168 (2)
H5	1.1620	−0.8771	0.8294	0.020*
C6	1.33727 (14)	−0.85338 (11)	0.72057 (8)	0.0146 (2)
C7	1.26143 (14)	−0.72922 (11)	0.67179 (8)	0.0154 (2)
H7	1.1583	−0.7016	0.6981	0.018*
C8	1.32174 (14)	−0.65096 (11)	0.59452 (8)	0.0163 (2)
H8	1.4237	−0.6766	0.5658	0.020*
C9	1.23652 (14)	−0.52594 (11)	0.55168 (8)	0.0154 (2)
O6	0.63568 (10)	0.40327 (8)	0.21083 (5)	0.01890 (19)
N3	0.33210 (12)	0.83883 (9)	0.12744 (6)	0.0165 (2)
N4	0.49527 (13)	0.41488 (10)	0.34804 (7)	0.0166 (2)
C25	0.47045 (14)	0.78510 (11)	0.09248 (8)	0.0163 (2)
H25	0.5246	0.8324	0.0372	0.020*
C26	0.53794 (14)	0.66340 (11)	0.13348 (8)	0.0149 (2)
H26	0.6352	0.6275	0.1060	0.018*
C27	0.46153 (14)	0.59441 (10)	0.21541 (7)	0.0134 (2)
C28	0.31766 (14)	0.64967 (11)	0.25206 (8)	0.0157 (2)
H28	0.2617	0.6051	0.3077	0.019*
C29	0.25757 (15)	0.77131 (11)	0.20557 (8)	0.0179 (2)
H29	0.1587	0.8085	0.2304	0.021*
C30	0.53836 (14)	0.46205 (10)	0.25861 (8)	0.0137 (2)
O3	0.63597 (10)	0.16029 (8)	0.43624 (5)	0.01797 (19)
N1	0.96690 (12)	−0.26237 (9)	0.52294 (6)	0.0159 (2)
N2	0.80706 (13)	0.16582 (10)	0.30636 (7)	0.0162 (2)
C10	0.82051 (14)	−0.21608 (11)	0.55363 (8)	0.0158 (2)
H10	0.7640	−0.2676	0.6062	0.019*
C11	0.74758 (14)	−0.09641 (11)	0.51228 (7)	0.0144 (2)
H11	0.6437	−0.0666	0.5363	0.017*
C12	0.82925 (13)	−0.02068 (10)	0.43500 (7)	0.0123 (2)
C13	0.98052 (14)	−0.06896 (11)	0.40223 (7)	0.0144 (2)
H13	1.0389	−0.0202	0.3492	0.017*
C14	1.04491 (14)	−0.18963 (11)	0.44823 (8)	0.0153 (2)
H14	1.1486	−0.2219	0.4258	0.018*
C15	0.74901 (13)	0.11036 (10)	0.39157 (7)	0.0130 (2)
H2A	0.758 (2)	0.2406 (17)	0.2765 (11)	0.030 (4)*
H4B	0.539 (2)	0.3368 (18)	0.3756 (12)	0.039 (5)*
H4C	0.435 (2)	0.4608 (16)	0.3825 (11)	0.032 (4)*
H2B	0.881 (2)	0.1252 (16)	0.2711 (11)	0.035 (4)*
H1	1.055 (2)	−0.408 (2)	0.5688 (13)	0.055 (6)*
H4	0.249 (2)	0.984 (2)	0.0813 (13)	0.056 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0235 (5)	0.0166 (4)	0.0153 (4)	0.0090 (4)	0.0035 (3)	0.0022 (3)
O5	0.0226 (5)	0.0190 (4)	0.0143 (4)	0.0065 (4)	0.0022 (3)	0.0034 (3)
C16	0.0162 (6)	0.0156 (5)	0.0130 (5)	−0.0022 (4)	−0.0001 (4)	−0.0003 (4)
C17	0.0147 (6)	0.0161 (6)	0.0188 (6)	0.0030 (4)	−0.0021 (4)	−0.0034 (4)
C18	0.0220 (6)	0.0129 (5)	0.0161 (5)	0.0022 (5)	−0.0060 (4)	−0.0009 (4)
C19	0.0216 (6)	0.0150 (5)	0.0127 (5)	−0.0017 (5)	−0.0015 (4)	0.0010 (4)
C20	0.0155 (6)	0.0154 (5)	0.0144 (5)	0.0003 (4)	−0.0006 (4)	−0.0016 (4)
C21	0.0148 (5)	0.0125 (5)	0.0134 (5)	−0.0010 (4)	−0.0032 (4)	−0.0008 (4)
C22	0.0140 (5)	0.0127 (5)	0.0163 (5)	0.0004 (4)	−0.0007 (4)	−0.0016 (4)
C23	0.0158 (6)	0.0132 (5)	0.0155 (5)	0.0018 (4)	−0.0006 (4)	−0.0020 (4)
C24	0.0150 (5)	0.0128 (5)	0.0151 (5)	0.0001 (4)	0.0000 (4)	−0.0008 (4)
O1	0.0236 (5)	0.0166 (4)	0.0177 (4)	0.0094 (4)	0.0038 (3)	0.0033 (3)
O2	0.0237 (5)	0.0164 (4)	0.0156 (4)	0.0056 (3)	0.0014 (3)	0.0016 (3)
C1	0.0190 (6)	0.0149 (5)	0.0144 (5)	0.0000 (5)	−0.0014 (4)	−0.0005 (4)
C2	0.0200 (6)	0.0171 (6)	0.0209 (6)	0.0050 (5)	−0.0030 (5)	−0.0030 (5)
C3	0.0282 (7)	0.0126 (5)	0.0178 (6)	0.0038 (5)	−0.0070 (5)	0.0007 (4)
C4	0.0260 (6)	0.0141 (5)	0.0139 (5)	−0.0015 (5)	−0.0021 (4)	−0.0002 (4)
C5	0.0192 (6)	0.0141 (5)	0.0169 (5)	0.0006 (5)	−0.0016 (4)	−0.0046 (4)
C6	0.0173 (6)	0.0113 (5)	0.0152 (5)	0.0004 (4)	−0.0049 (4)	−0.0023 (4)
C7	0.0175 (6)	0.0129 (5)	0.0156 (5)	0.0012 (4)	−0.0030 (4)	−0.0036 (4)
C8	0.0164 (6)	0.0146 (5)	0.0165 (5)	0.0040 (4)	−0.0025 (4)	−0.0028 (4)
C9	0.0178 (6)	0.0136 (5)	0.0134 (5)	0.0029 (4)	−0.0020 (4)	−0.0024 (4)
O6	0.0202 (4)	0.0152 (4)	0.0167 (4)	0.0059 (3)	0.0013 (3)	−0.0003 (3)
N3	0.0200 (5)	0.0122 (5)	0.0155 (5)	0.0022 (4)	−0.0032 (4)	−0.0007 (4)
N4	0.0189 (5)	0.0113 (5)	0.0150 (5)	0.0045 (4)	0.0009 (4)	0.0015 (4)
C25	0.0188 (6)	0.0137 (5)	0.0139 (5)	−0.0015 (4)	−0.0004 (4)	0.0009 (4)
C26	0.0140 (5)	0.0139 (5)	0.0149 (5)	0.0016 (4)	−0.0007 (4)	−0.0016 (4)
C27	0.0162 (5)	0.0098 (5)	0.0133 (5)	−0.0003 (4)	−0.0034 (4)	−0.0003 (4)
C28	0.0177 (6)	0.0126 (5)	0.0139 (5)	0.0010 (4)	0.0001 (4)	0.0004 (4)
C29	0.0178 (6)	0.0151 (6)	0.0178 (6)	0.0036 (5)	−0.0007 (4)	−0.0015 (4)
C30	0.0134 (5)	0.0106 (5)	0.0153 (5)	0.0000 (4)	−0.0019 (4)	−0.0001 (4)
O3	0.0186 (4)	0.0146 (4)	0.0162 (4)	0.0052 (3)	0.0025 (3)	−0.0003 (3)
N1	0.0180 (5)	0.0134 (5)	0.0143 (5)	0.0026 (4)	−0.0031 (4)	−0.0009 (4)
N2	0.0182 (5)	0.0120 (5)	0.0135 (5)	0.0051 (4)	0.0012 (4)	0.0017 (4)
C10	0.0179 (6)	0.0141 (5)	0.0127 (5)	−0.0009 (4)	−0.0007 (4)	0.0012 (4)
C11	0.0134 (5)	0.0143 (5)	0.0137 (5)	0.0011 (4)	−0.0001 (4)	−0.0018 (4)
C12	0.0139 (5)	0.0111 (5)	0.0116 (5)	0.0006 (4)	−0.0029 (4)	−0.0020 (4)
C13	0.0151 (6)	0.0139 (5)	0.0119 (5)	0.0000 (4)	−0.0004 (4)	0.0001 (4)
C14	0.0138 (5)	0.0153 (5)	0.0148 (5)	0.0030 (4)	−0.0007 (4)	−0.0022 (4)
C15	0.0135 (5)	0.0100 (5)	0.0141 (5)	0.0006 (4)	−0.0026 (4)	−0.0006 (4)

Geometric parameters (Å, º)

O4—C24	1.3168 (14)	C7—H7	0.9500
O4—H4	0.98 (2)	C7—C8	1.3324 (16)
O5—C24	1.2236 (13)	C8—H8	0.9500
C16—H16	0.9500	C8—C9	1.4783 (16)
C16—C17	1.3863 (16)	O6—C30	1.2345 (14)
C16—C21	1.4000 (16)	N3—C25	1.3375 (16)
C17—H17	0.9500	N3—C29	1.3385 (15)
C17—C18	1.3900 (16)	N4—C30	1.3347 (15)
C18—H18	0.9500	N4—H4B	0.894 (19)
C18—C19	1.3819 (17)	N4—H4C	0.872 (17)
C19—H19	0.9500	C25—H25	0.9500
C19—C20	1.3886 (16)	C25—C26	1.3839 (16)
C20—H20	0.9500	C26—H26	0.9500
C20—C21	1.3968 (15)	C26—C27	1.3904 (15)
C21—C22	1.4666 (15)	C27—C28	1.3898 (16)
C22—H22	0.9500	C27—C30	1.5102 (15)
C22—C23	1.3303 (16)	C28—H28	0.9500
C23—H23	0.9500	C28—C29	1.3869 (16)
C23—C24	1.4771 (16)	C29—H29	0.9500
O1—C9	1.3160 (14)	O3—C15	1.2355 (14)
O1—H1	0.97 (2)	N1—C10	1.3389 (15)
O2—C9	1.2243 (14)	N1—C14	1.3395 (14)
C1—H1A	0.9500	N2—C15	1.3289 (14)
C1—C2	1.3867 (16)	N2—H2A	0.897 (17)
C1—C6	1.3976 (17)	N2—H2B	0.906 (18)
C2—H2	0.9500	C10—H10	0.9500
C2—C3	1.3910 (17)	C10—C11	1.3862 (16)
C3—H3	0.9500	C11—H11	0.9500
C3—C4	1.3844 (18)	C11—C12	1.3916 (15)
C4—H4A	0.9500	C12—C13	1.3902 (16)
C4—C5	1.3877 (16)	C12—C15	1.5114 (15)
C5—H5	0.9500	C13—H13	0.9500
C5—C6	1.3979 (16)	C13—C14	1.3888 (16)
C6—C7	1.4664 (15)	C14—H14	0.9500
C24—O4—H4	109.9 (11)	C7—C8—H8	118.6
C17—C16—H16	120.0	C7—C8—C9	122.71 (11)
C17—C16—C21	119.93 (10)	C9—C8—H8	118.6
C21—C16—H16	120.0	O1—C9—C8	114.71 (10)
C16—C17—H17	119.8	O2—C9—O1	123.22 (11)
C16—C17—C18	120.44 (11)	O2—C9—C8	122.07 (11)
C18—C17—H17	119.8	C25—N3—C29	117.98 (10)
C17—C18—H18	119.9	C30—N4—H4B	119.0 (11)
C19—C18—C17	120.14 (11)	C30—N4—H4C	122.6 (11)
C19—C18—H18	119.9	H4B—N4—H4C	117.9 (15)
C18—C19—H19	120.2	N3—C25—H25	118.6
C18—C19—C20	119.67 (11)	N3—C25—C26	122.71 (10)
C20—C19—H19	120.2	C26—C25—H25	118.6
C19—C20—H20	119.6	C25—C26—H26	120.4
C19—C20—C21	120.86 (11)	C25—C26—C27	119.16 (11)
C21—C20—H20	119.6	C27—C26—H26	120.4
C16—C21—C22	122.55 (10)	C26—C27—C30	117.91 (10)
C20—C21—C16	118.93 (10)	C28—C27—C26	118.41 (10)
C20—C21—C22	118.52 (10)	C28—C27—C30	123.67 (10)
C21—C22—H22	116.5	C27—C28—H28	120.7
C23—C22—C21	127.00 (11)	C29—C28—C27	118.51 (10)
C23—C22—H22	116.5	C29—C28—H28	120.7
C22—C23—H23	118.6	N3—C29—C28	123.23 (11)
C22—C23—C24	122.74 (11)	N3—C29—H29	118.4
C24—C23—H23	118.6	C28—C29—H29	118.4
O4—C24—C23	115.49 (10)	O6—C30—N4	123.51 (11)
O5—C24—O4	122.54 (11)	O6—C30—C27	119.52 (10)
O5—C24—C23	121.97 (10)	N4—C30—C27	116.97 (10)
C9—O1—H1	110.4 (11)	C10—N1—C14	118.07 (10)
C2—C1—H1A	120.0	C15—N2—H2A	119.8 (10)
C2—C1—C6	119.99 (11)	C15—N2—H2B	123.7 (10)
C6—C1—H1A	120.0	H2A—N2—H2B	115.3 (14)
C1—C2—H2	119.7	N1—C10—H10	118.5
C1—C2—C3	120.53 (12)	N1—C10—C11	123.02 (10)
C3—C2—H2	119.7	C11—C10—H10	118.5
C2—C3—H3	120.0	C10—C11—H11	120.6
C4—C3—C2	119.94 (11)	C10—C11—C12	118.80 (11)
C4—C3—H3	120.0	C12—C11—H11	120.6
C3—C4—H4A	120.1	C11—C12—C15	118.11 (10)
C3—C4—C5	119.71 (11)	C13—C12—C11	118.40 (10)
C5—C4—H4A	120.1	C13—C12—C15	123.49 (10)
C4—C5—H5	119.5	C12—C13—H13	120.5
C4—C5—C6	120.91 (11)	C14—C13—C12	118.97 (10)
C6—C5—H5	119.5	C14—C13—H13	120.5
C1—C6—C5	118.90 (10)	N1—C14—C13	122.74 (11)
C1—C6—C7	122.87 (10)	N1—C14—H14	118.6
C5—C6—C7	118.22 (10)	C13—C14—H14	118.6
C6—C7—H7	116.5	O3—C15—N2	123.78 (11)
C8—C7—C6	126.95 (11)	O3—C15—C12	119.31 (10)
C8—C7—H7	116.5	N2—C15—C12	116.91 (10)
C16—C17—C18—C19	−0.32 (17)	C7—C8—C9—O2	−174.24 (11)
C16—C21—C22—C23	−12.75 (18)	N3—C25—C26—C27	−1.37 (17)
C17—C16—C21—C20	1.28 (16)	C25—N3—C29—C28	0.67 (17)
C17—C16—C21—C22	−177.96 (10)	C25—C26—C27—C28	1.35 (16)
C17—C18—C19—C20	1.60 (17)	C25—C26—C27—C30	−179.83 (10)
C18—C19—C20—C21	−1.45 (17)	C26—C27—C28—C29	−0.41 (16)
C19—C20—C21—C16	0.01 (16)	C26—C27—C30—O6	−20.32 (15)
C19—C20—C21—C22	179.27 (10)	C26—C27—C30—N4	159.89 (10)
C20—C21—C22—C23	168.01 (11)	C27—C28—C29—N3	−0.63 (17)
C21—C16—C17—C18	−1.13 (17)	C28—C27—C30—O6	158.43 (11)
C21—C22—C23—C24	179.18 (10)	C28—C27—C30—N4	−21.36 (16)
C22—C23—C24—O4	−3.18 (16)	C29—N3—C25—C26	0.35 (17)
C22—C23—C24—O5	177.43 (11)	C30—C27—C28—C29	−179.15 (10)
C1—C2—C3—C4	0.44 (18)	N1—C10—C11—C12	0.35 (17)
C1—C6—C7—C8	−5.52 (18)	C10—N1—C14—C13	0.35 (16)
C2—C1—C6—C5	−1.36 (16)	C10—C11—C12—C13	0.39 (15)
C2—C1—C6—C7	177.59 (10)	C10—C11—C12—C15	−179.14 (9)
C2—C3—C4—C5	−0.37 (17)	C11—C12—C13—C14	−0.73 (15)
C3—C4—C5—C6	−0.57 (17)	C11—C12—C15—O3	17.43 (15)
C4—C5—C6—C1	1.43 (16)	C11—C12—C15—N2	−163.17 (10)
C4—C5—C6—C7	−177.56 (10)	C12—C13—C14—N1	0.38 (17)
C5—C6—C7—C8	173.42 (11)	C13—C12—C15—O3	−162.08 (10)
C6—C1—C2—C3	0.44 (17)	C13—C12—C15—N2	17.32 (15)
C6—C7—C8—C9	−178.73 (10)	C14—N1—C10—C11	−0.72 (16)
C7—C8—C9—O1	5.87 (16)	C15—C12—C13—C14	178.77 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O6	0.897 (17)	2.015 (18)	2.9111 (13)	176.4 (14)
N4—H4B···O3	0.894 (19)	2.010 (19)	2.9039 (13)	179.2 (16)
N4—H4C···O2^i	0.872 (17)	2.042 (18)	2.9057 (14)	170.8 (15)
N2—H2B···O5^ii	0.906 (18)	2.010 (18)	2.9084 (14)	171.2 (15)
O1—H1···N1	0.97 (2)	1.67 (2)	2.6415 (13)	175.7 (18)
O4—H4···N3	0.98 (2)	1.65 (2)	2.6331 (13)	175.8 (18)

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

(1C)

Crystal data

C9H8O2·C6H6N2O	F(000) = 568
Mr = 270.28	Dx = 1.339 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.0191 (7) Å	Cell parameters from 1764 reflections
b = 6.1871 (3) Å	θ = 2.6–24.1°
c = 16.6387 (7) Å	µ = 0.10 mm^−1
β = 111.740 (3)°	T = 100 K
V = 1340.56 (11) Å^3	Plate, colourless
Z = 4	0.22 × 0.15 × 0.13 mm

Data collection

Bruker Apex II kappa CCD area detector diffractometer	3188 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 27.9°, θmin = 2.5°
Absorption correction: multi-scan SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0556 before and 0.0477 after correction. The Ratio of minimum to maximum transmission is 0.8651. The λ/2 correction factor is 0.00150.	h = −18→18
Tmin = 0.645, Tmax = 0.746	k = −8→8
11465 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 0.3914P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3188 reflections	Δρmax = 0.23 e Å^−3
193 parameters	Δρmin = −0.22 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.79656 (10)	0.8405 (2)	0.47882 (8)	0.0289 (3)
O2	0.69757 (10)	0.54586 (19)	0.45016 (7)	0.0254 (3)
C1	0.92031 (13)	0.4960 (3)	0.78234 (11)	0.0241 (4)
H1A	0.9357	0.6351	0.7661	0.029*
C2	0.96108 (14)	0.4335 (3)	0.86836 (12)	0.0285 (4)
H2	1.0042	0.5298	0.9108	0.034*
C3	0.93925 (15)	0.2307 (3)	0.89288 (12)	0.0285 (4)
H3	0.9666	0.1893	0.9520	0.034*
C4	0.87773 (14)	0.0893 (3)	0.83128 (11)	0.0262 (4)
H4	0.8635	−0.0501	0.8480	0.031*
C5	0.83645 (14)	0.1506 (3)	0.74471 (11)	0.0230 (4)
H5	0.7943	0.0523	0.7027	0.028*
C6	0.85638 (13)	0.3552 (3)	0.71899 (11)	0.0202 (4)
C7	0.80849 (13)	0.4173 (3)	0.62776 (11)	0.0215 (4)
H7	0.7690	0.3101	0.5887	0.026*
C8	0.81507 (13)	0.6100 (3)	0.59448 (10)	0.0222 (4)
H8	0.8545	0.7199	0.6320	0.027*
C9	0.76360 (13)	0.6593 (3)	0.50161 (11)	0.0213 (4)
O3	0.61199 (9)	0.58159 (19)	0.09418 (7)	0.0242 (3)
N1	0.68859 (11)	0.9531 (2)	0.31731 (9)	0.0208 (3)
N2	0.45757 (12)	0.7479 (2)	0.03656 (9)	0.0212 (3)
C10	0.65118 (14)	1.1554 (3)	0.30859 (11)	0.0220 (4)
H10	0.6748	1.2492	0.3572	0.026*
C11	0.58007 (14)	1.2328 (3)	0.23228 (11)	0.0215 (4)
H11	0.5553	1.3768	0.2287	0.026*
C12	0.54505 (13)	1.0975 (3)	0.16070 (10)	0.0184 (4)
H12	0.4951	1.1463	0.1077	0.022*
C13	0.58455 (13)	0.8889 (3)	0.16816 (10)	0.0178 (4)
C14	0.65602 (13)	0.8244 (3)	0.24776 (10)	0.0194 (4)
H14	0.6830	0.6821	0.2530	0.023*
C15	0.55197 (13)	0.7280 (3)	0.09573 (10)	0.0185 (4)
H2A	0.4114 (16)	0.852 (3)	0.0410 (13)	0.040 (6)*
H2B	0.4385 (16)	0.645 (3)	−0.0056 (13)	0.037 (6)*
H1	0.757 (2)	0.872 (4)	0.4165 (17)	0.069 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0322 (8)	0.0285 (7)	0.0200 (7)	−0.0124 (6)	0.0026 (6)	0.0025 (6)
O2	0.0283 (7)	0.0230 (7)	0.0219 (6)	−0.0072 (5)	0.0056 (5)	−0.0040 (5)
C1	0.0225 (9)	0.0221 (9)	0.0257 (9)	−0.0001 (7)	0.0067 (8)	−0.0011 (7)
C2	0.0261 (10)	0.0295 (10)	0.0248 (9)	0.0004 (8)	0.0034 (8)	−0.0024 (8)
C3	0.0261 (10)	0.0343 (10)	0.0213 (9)	0.0047 (8)	0.0043 (8)	0.0030 (8)
C4	0.0266 (10)	0.0245 (10)	0.0284 (10)	0.0022 (8)	0.0111 (8)	0.0063 (8)
C5	0.0231 (9)	0.0213 (9)	0.0250 (9)	0.0002 (7)	0.0095 (8)	−0.0017 (7)
C6	0.0182 (9)	0.0209 (9)	0.0217 (9)	0.0021 (7)	0.0075 (7)	−0.0004 (7)
C7	0.0207 (9)	0.0223 (9)	0.0211 (8)	0.0006 (7)	0.0072 (7)	−0.0028 (7)
C8	0.0222 (9)	0.0240 (9)	0.0190 (9)	−0.0047 (7)	0.0060 (7)	−0.0029 (7)
C9	0.0209 (9)	0.0213 (9)	0.0224 (9)	−0.0026 (7)	0.0090 (8)	−0.0015 (7)
O3	0.0271 (7)	0.0208 (6)	0.0223 (6)	0.0029 (5)	0.0063 (5)	−0.0056 (5)
N1	0.0243 (8)	0.0213 (7)	0.0176 (7)	−0.0055 (6)	0.0087 (6)	−0.0027 (6)
N2	0.0253 (8)	0.0193 (7)	0.0170 (7)	0.0014 (6)	0.0053 (6)	−0.0052 (6)
C10	0.0273 (10)	0.0212 (9)	0.0214 (9)	−0.0077 (7)	0.0137 (8)	−0.0057 (7)
C11	0.0272 (10)	0.0159 (8)	0.0253 (9)	−0.0028 (7)	0.0142 (8)	−0.0030 (7)
C12	0.0218 (9)	0.0174 (8)	0.0176 (8)	−0.0025 (7)	0.0091 (7)	0.0003 (7)
C13	0.0199 (9)	0.0189 (8)	0.0154 (8)	−0.0026 (7)	0.0075 (7)	−0.0023 (7)
C14	0.0215 (9)	0.0175 (8)	0.0198 (8)	−0.0033 (7)	0.0083 (7)	−0.0025 (7)
C15	0.0256 (9)	0.0160 (8)	0.0159 (8)	−0.0011 (7)	0.0102 (7)	−0.0002 (7)

Geometric parameters (Å, º)

O1—C9	1.321 (2)	C8—H8	0.9500
O1—H1	1.00 (3)	C8—C9	1.475 (2)
O2—C9	1.223 (2)	O3—C15	1.243 (2)
C1—H1A	0.9500	N1—C10	1.344 (2)
C1—C2	1.385 (2)	N1—C14	1.338 (2)
C1—C6	1.405 (2)	N2—C15	1.331 (2)
C2—H2	0.9500	N2—H2A	0.94 (2)
C2—C3	1.388 (3)	N2—H2B	0.91 (2)
C3—H3	0.9500	C10—H10	0.9500
C3—C4	1.380 (3)	C10—C11	1.378 (2)
C4—H4	0.9500	C11—H11	0.9500
C4—C5	1.391 (2)	C11—C12	1.388 (2)
C5—H5	0.9500	C12—H12	0.9500
C5—C6	1.397 (2)	C12—C13	1.392 (2)
C6—C7	1.466 (2)	C13—C14	1.391 (2)
C7—H7	0.9500	C13—C15	1.498 (2)
C7—C8	1.332 (2)	C14—H14	0.9500
C9—O1—H1	110.1 (15)	O1—C9—C8	112.89 (15)
C2—C1—H1A	119.8	O2—C9—O1	122.74 (15)
C2—C1—C6	120.42 (17)	O2—C9—C8	124.37 (16)
C6—C1—H1A	119.8	C14—N1—C10	117.79 (15)
C1—C2—H2	119.8	C15—N2—H2A	122.2 (12)
C1—C2—C3	120.30 (18)	C15—N2—H2B	115.6 (13)
C3—C2—H2	119.8	H2A—N2—H2B	121.9 (18)
C2—C3—H3	120.0	N1—C10—H10	118.5
C4—C3—C2	120.00 (17)	N1—C10—C11	122.93 (16)
C4—C3—H3	120.0	C11—C10—H10	118.5
C3—C4—H4	119.9	C10—C11—H11	120.5
C3—C4—C5	120.12 (17)	C10—C11—C12	119.09 (16)
C5—C4—H4	119.9	C12—C11—H11	120.5
C4—C5—H5	119.7	C11—C12—H12	120.6
C4—C5—C6	120.69 (17)	C11—C12—C13	118.70 (15)
C6—C5—H5	119.7	C13—C12—H12	120.6
C1—C6—C7	122.32 (16)	C12—C13—C15	123.48 (15)
C5—C6—C1	118.46 (16)	C14—C13—C12	118.25 (15)
C5—C6—C7	119.20 (16)	C14—C13—C15	118.24 (15)
C6—C7—H7	116.9	N1—C14—C13	123.21 (16)
C8—C7—C6	126.13 (16)	N1—C14—H14	118.4
C8—C7—H7	116.9	C13—C14—H14	118.4
C7—C8—H8	118.7	O3—C15—N2	123.17 (15)
C7—C8—C9	122.57 (16)	O3—C15—C13	119.59 (15)
C9—C8—H8	118.7	N2—C15—C13	117.22 (15)
C1—C2—C3—C4	0.8 (3)	N1—C10—C11—C12	−0.1 (3)
C1—C6—C7—C8	−3.0 (3)	C10—N1—C14—C13	−1.2 (2)
C2—C1—C6—C5	−1.0 (3)	C10—C11—C12—C13	−1.2 (2)
C2—C1—C6—C7	177.70 (16)	C11—C12—C13—C14	1.2 (2)
C2—C3—C4—C5	−0.8 (3)	C11—C12—C13—C15	179.43 (15)
C3—C4—C5—C6	−0.1 (3)	C12—C13—C14—N1	−0.1 (2)
C4—C5—C6—C1	1.0 (3)	C12—C13—C15—O3	153.95 (16)
C4—C5—C6—C7	−177.71 (16)	C12—C13—C15—N2	−27.5 (2)
C5—C6—C7—C8	175.69 (18)	C14—N1—C10—C11	1.3 (2)
C6—C1—C2—C3	0.1 (3)	C14—C13—C15—O3	−27.9 (2)
C6—C7—C8—C9	−179.54 (16)	C14—C13—C15—N2	150.67 (16)
C7—C8—C9—O1	−166.61 (17)	C15—C13—C14—N1	−178.35 (15)
C7—C8—C9—O2	13.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2^i	0.94 (2)	1.99 (2)	2.921 (2)	173.4 (19)
N2—H2B···O3^ii	0.91 (2)	1.97 (2)	2.8753 (19)	175.6 (19)
O1—H1···N1	1.00 (3)	1.65 (3)	2.6431 (18)	173 (2)

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

(2A)

Crystal data

2(C10H10O2)·C10H8N2	Z = 4
Mr = 480.54	F(000) = 1016
Triclinic, P1	Dx = 1.298 Mg m^−3
a = 10.8843 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.6510 (4) Å	Cell parameters from 9994 reflections
c = 16.6073 (4) Å	θ = 2.2–28.0°
α = 63.358 (1)°	µ = 0.09 mm^−1
β = 79.726 (1)°	T = 100 K
γ = 77.722 (1)°	Block, colourless
V = 2459.66 (10) Å^3	0.67 × 0.4 × 0.27 mm

Data collection

Bruker Apex II kappa CCD area detector diffractometer	11862 independent reflections
Radiation source: fine-focus sealed tube	8260 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 28.0°, θmin = 1.4°
Absorption correction: multi-scan SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0760 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.7952. The λ/2 correction factor is 0.00150.	h = −14→13
Tmin = 0.593, Tmax = 0.746	k = −20→20
45365 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.138	w = 1/[σ^2(Fo^2) + (0.0619P)^2 + 0.9528P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
11862 reflections	Δρmax = 0.81 e Å^−3
740 parameters	Δρmin = −0.35 e Å^−3
331 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O3	0.54805 (11)	0.43247 (9)	0.16778 (8)	0.0272 (3)
O4	0.36636 (10)	0.46320 (8)	0.10704 (8)	0.0236 (3)
C11	0.2414 (2)	0.86946 (13)	0.36601 (12)	0.0342 (4)
H11A	0.1563	0.8995	0.3474	0.051*
H11B	0.2981	0.9183	0.3383	0.051*
H11C	0.2387	0.8424	0.4321	0.051*
C12	0.28922 (17)	0.78968 (11)	0.33562 (10)	0.0244 (4)
C13	0.20905 (16)	0.75892 (12)	0.30023 (10)	0.0236 (3)
H13	0.1234	0.7888	0.2952	0.028*
C14	0.25243 (15)	0.68555 (11)	0.27230 (10)	0.0210 (3)
H14	0.1957	0.6646	0.2500	0.025*
C15	0.37925 (15)	0.64205 (11)	0.27665 (10)	0.0197 (3)
C16	0.45866 (16)	0.67262 (12)	0.31235 (11)	0.0246 (4)
H16	0.5448	0.6438	0.3166	0.029*
C17	0.41346 (17)	0.74472 (12)	0.34181 (11)	0.0280 (4)
H17	0.4691	0.7636	0.3668	0.034*
C18	0.43251 (15)	0.56928 (11)	0.24174 (10)	0.0204 (3)
H18	0.5172	0.5393	0.2529	0.024*
C19	0.37362 (15)	0.54128 (11)	0.19607 (10)	0.0196 (3)
H19	0.2867	0.5655	0.1882	0.024*
C20	0.44001 (15)	0.47322 (11)	0.15717 (10)	0.0194 (3)
N3	0.61728 (15)	−0.00502 (10)	−0.14870 (9)	0.0298 (3)
N4	0.45502 (12)	0.33720 (9)	0.03677 (9)	0.0203 (3)
C51	0.70307 (18)	0.02053 (12)	−0.11942 (11)	0.0285 (4)
H51	0.7889	−0.0075	−0.1245	0.034*
C52	0.67290 (17)	0.08598 (11)	−0.08192 (11)	0.0245 (4)
H52	0.7370	0.1008	−0.0602	0.029*
C53	0.54832 (15)	0.13051 (11)	−0.07582 (10)	0.0199 (3)
C54	0.45892 (17)	0.10585 (12)	−0.10904 (10)	0.0259 (4)
H54	0.3731	0.1352	−0.1079	0.031*
C55	0.49810 (19)	0.03688 (12)	−0.14413 (11)	0.0298 (4)
H55	0.4366	0.0193	−0.1656	0.036*
C56	0.51363 (14)	0.20124 (11)	−0.03596 (10)	0.0177 (3)
C57	0.58241 (15)	0.19534 (11)	0.03027 (10)	0.0191 (3)
H57	0.6509	0.1446	0.0517	0.023*
C58	0.55001 (15)	0.26381 (11)	0.06422 (10)	0.0210 (3)
H58	0.5975	0.2586	0.1094	0.025*
C59	0.38905 (15)	0.34236 (11)	−0.02619 (10)	0.0210 (3)
H59	0.3212	0.3940	−0.0463	0.025*
C60	0.41400 (15)	0.27673 (11)	−0.06381 (10)	0.0200 (3)
H60	0.3637	0.2832	−0.1080	0.024*
N1	0.95749 (12)	0.48209 (9)	0.16623 (8)	0.0197 (3)
N2	0.97896 (13)	0.18645 (10)	−0.05978 (9)	0.0233 (3)
C41	0.85133 (15)	0.46070 (11)	0.15431 (10)	0.0190 (3)
H41	0.7728	0.4865	0.1765	0.023*
C42	0.85034 (14)	0.40290 (11)	0.11135 (10)	0.0171 (3)
H42	0.7725	0.3908	0.1032	0.021*
C43	0.96476 (14)	0.36243 (10)	0.07998 (9)	0.0155 (3)
C44	1.07513 (14)	0.38321 (11)	0.09451 (10)	0.0191 (3)
H44	1.1553	0.3561	0.0757	0.023*
C45	1.06732 (15)	0.44329 (11)	0.13640 (10)	0.0201 (3)
H45	1.1435	0.4578	0.1444	0.024*
C46	0.96939 (14)	0.30089 (10)	0.03262 (10)	0.0168 (3)
C47	0.86881 (15)	0.30931 (11)	−0.01310 (10)	0.0189 (3)
H47	0.7949	0.3546	−0.0140	0.023*
C48	0.87753 (16)	0.25092 (11)	−0.05729 (10)	0.0220 (3)
H48	0.8075	0.2571	−0.0875	0.026*
C49	1.07578 (16)	0.17855 (12)	−0.01626 (11)	0.0239 (4)
H49	1.1489	0.1332	−0.0174	0.029*
C50	1.07504 (15)	0.23309 (11)	0.03047 (11)	0.0213 (3)
H50	1.1460	0.2244	0.0609	0.026*
O5	0.53192 (12)	−0.09933 (9)	−0.27011 (9)	0.0362 (3)
O6	0.70598 (12)	−0.14788 (9)	−0.19878 (9)	0.0307 (3)
C21	0.7854 (2)	−0.51456 (14)	−0.49925 (13)	0.0427 (5)
H21A	0.7338	−0.5667	−0.4688	0.064*
H21B	0.8748	−0.5418	−0.4924	0.064*
H21C	0.7723	−0.4812	−0.5637	0.064*
C22	0.74751 (18)	−0.44377 (12)	−0.45744 (11)	0.0276 (4)
C23	0.82674 (18)	−0.43799 (12)	−0.40318 (11)	0.0291 (4)
H23	0.9058	−0.4790	−0.3922	0.035*
C24	0.79020 (18)	−0.37213 (13)	−0.36491 (11)	0.0289 (4)
H24	0.8443	−0.3694	−0.3274	0.035*
C25	0.67507 (17)	−0.31018 (11)	−0.38106 (11)	0.0267 (4)
C26	0.59878 (18)	−0.31647 (13)	−0.43548 (11)	0.0314 (4)
H26	0.5207	−0.2743	−0.4482	0.038*
C27	0.63368 (19)	−0.38262 (13)	−0.47165 (11)	0.0323 (4)
H27	0.5779	−0.3864	−0.5075	0.039*
C28	0.63152 (17)	−0.23861 (12)	−0.34284 (11)	0.0270 (4)
H28	0.5566	−0.1951	−0.3639	0.032*
C29	0.68416 (16)	−0.22810 (12)	−0.28320 (11)	0.0257 (4)
H29	0.7583	−0.2710	−0.2596	0.031*
C30	0.63251 (15)	−0.15227 (11)	−0.25153 (10)	0.0209 (3)
O1	0.9802 (8)	0.0746 (9)	−0.1401 (10)	0.0298 (15)	0.529
H1	0.9855	0.0983	−0.1046	0.045*	0.529
O2	1.1856 (6)	0.0180 (4)	−0.1198 (4)	0.0250 (13)	0.529
C1	1.1710 (17)	−0.3371 (11)	−0.3954 (12)	0.0402 (9)	0.529
H1A	1.1799	−0.4045	−0.3500	0.060*	0.529
H1B	1.2433	−0.3281	−0.4415	0.060*	0.529
H1C	1.0928	−0.3214	−0.4241	0.060*	0.529
C5	1.1685 (3)	−0.1526 (2)	−0.2657 (2)	0.0144 (8)	0.529
C4	1.2805 (3)	−0.2050 (3)	−0.2849 (3)	0.0191 (9)	0.529
H4A	1.3579	−0.2004	−0.2693	0.023*	0.529
C3	1.2793 (5)	−0.2641 (5)	−0.3271 (5)	0.0253 (10)	0.529
H3	1.3558	−0.2999	−0.3402	0.030*	0.529
C2	1.1660 (7)	−0.2707 (7)	−0.3499 (7)	0.0233 (4)	0.529
C7	1.0540 (5)	−0.2183 (6)	−0.3307 (7)	0.0217 (11)	0.529
H7	0.9766	−0.2229	−0.3463	0.026*	0.529
C6	1.0552 (3)	−0.1593 (4)	−0.2886 (4)	0.0162 (9)	0.529
H6A	0.9787	−0.1234	−0.2754	0.019*	0.529
C8	1.1727 (3)	−0.0915 (2)	−0.21908 (18)	0.0171 (6)	0.529
H8	1.2531	−0.0918	−0.2042	0.020*	0.529
C9	1.0757 (3)	−0.0367 (2)	−0.1961 (2)	0.0195 (6)	0.529
H9	0.9941	−0.0343	−0.2107	0.023*	0.529
C10	1.0895 (6)	0.0205 (5)	−0.1489 (5)	0.0183 (13)	0.529
O7	0.76739 (11)	0.64967 (9)	0.22511 (9)	0.0315 (3)
O8	0.97053 (11)	0.59150 (9)	0.24642 (9)	0.0272 (3)
C31	0.7637 (2)	0.99852 (13)	0.51001 (12)	0.0335 (4)
H31A	0.6758	1.0176	0.5291	0.050*
H31B	0.8020	1.0565	0.4701	0.050*
H31C	0.8108	0.9609	0.5634	0.050*
C32	0.76741 (17)	0.93785 (11)	0.45982 (10)	0.0246 (4)
C33	0.66665 (17)	0.94784 (12)	0.41387 (11)	0.0255 (4)
H33	0.5934	0.9932	0.4144	0.031*
C34	0.67163 (16)	0.89241 (11)	0.36715 (11)	0.0228 (3)
H34	0.6019	0.9009	0.3357	0.027*
C35	0.77717 (15)	0.82436 (11)	0.36550 (10)	0.0198 (3)
C36	0.87811 (16)	0.81396 (12)	0.41207 (10)	0.0238 (4)
H36	0.9507	0.7677	0.4127	0.029*
C37	0.87324 (17)	0.87065 (12)	0.45742 (11)	0.0264 (4)
H37	0.9438	0.8635	0.4876	0.032*
C38	0.77859 (15)	0.76655 (11)	0.31602 (10)	0.0205 (3)
H38	0.7037	0.7759	0.2893	0.025*
C39	0.87349 (16)	0.70243 (11)	0.30458 (10)	0.0219 (3)
H39	0.9504	0.6919	0.3295	0.026*
C40	0.86315 (15)	0.64715 (11)	0.25445 (10)	0.0194 (3)
O1A	1.0125 (8)	0.0636 (9)	−0.1451 (10)	0.0227 (14)	0.471
H1AA	1.0063	0.1088	−0.1298	0.034*	0.471
O2A	1.2092 (7)	0.0314 (5)	−0.1058 (5)	0.0255 (11)	0.471
C1A	1.1809 (19)	−0.3365 (13)	−0.3904 (14)	0.0402 (9)	0.471
H1AB	1.1594	−0.3011	−0.4531	0.060*	0.471
H1AC	1.1261	−0.3860	−0.3564	0.060*	0.471
H1AD	1.2693	−0.3675	−0.3896	0.060*	0.471
C5A	1.1152 (3)	−0.1381 (3)	−0.2676 (3)	0.0137 (9)	0.471
C6A	1.0160 (3)	−0.1582 (5)	−0.2955 (5)	0.0192 (10)	0.471
H6AA	0.9322	−0.1281	−0.2874	0.023*	0.471
C7A	1.0396 (6)	−0.2224 (7)	−0.3352 (8)	0.0230 (12)	0.471
H7A	0.9718	−0.2361	−0.3542	0.028*	0.471
C2A	1.1622 (7)	−0.2664 (7)	−0.3470 (8)	0.0233 (4)	0.471
C3A	1.2614 (5)	−0.2462 (5)	−0.3191 (6)	0.0226 (11)	0.471
H3A	1.3452	−0.2763	−0.3271	0.027*	0.471
C4A	1.2378 (3)	−0.1821 (3)	−0.2794 (3)	0.0149 (10)	0.471
H4AA	1.3056	−0.1683	−0.2603	0.018*	0.471
C8A	1.0841 (4)	−0.0690 (3)	−0.2246 (2)	0.0190 (7)	0.471
H8AA	0.9988	−0.0389	−0.2229	0.023*	0.471
C9A	1.1642 (4)	−0.0458 (2)	−0.1886 (2)	0.0196 (7)	0.471
H9A	1.2504	−0.0733	−0.1931	0.024*	0.471
C10A	1.1320 (6)	0.0186 (5)	−0.1423 (5)	0.0153 (16)	0.471
H8A	0.961 (2)	0.5566 (19)	0.2153 (17)	0.068 (8)*
H4	0.410 (2)	0.4165 (19)	0.0835 (16)	0.069 (8)*
H6	0.669 (3)	−0.0938 (15)	−0.1809 (19)	0.093 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0218 (6)	0.0286 (6)	0.0345 (7)	−0.0002 (5)	−0.0053 (5)	−0.0169 (5)
O4	0.0224 (6)	0.0243 (6)	0.0331 (6)	−0.0005 (5)	−0.0032 (5)	−0.0213 (5)
C11	0.0558 (12)	0.0243 (9)	0.0277 (9)	−0.0099 (8)	0.0010 (8)	−0.0159 (8)
C12	0.0406 (10)	0.0174 (8)	0.0162 (7)	−0.0094 (7)	0.0013 (7)	−0.0075 (6)
C13	0.0318 (9)	0.0204 (8)	0.0181 (7)	−0.0029 (7)	−0.0010 (6)	−0.0087 (6)
C14	0.0284 (9)	0.0208 (8)	0.0166 (7)	−0.0071 (6)	−0.0032 (6)	−0.0087 (6)
C15	0.0287 (8)	0.0163 (7)	0.0146 (7)	−0.0074 (6)	0.0015 (6)	−0.0064 (6)
C16	0.0271 (9)	0.0253 (9)	0.0241 (8)	−0.0078 (7)	−0.0017 (7)	−0.0116 (7)
C17	0.0392 (10)	0.0271 (9)	0.0253 (8)	−0.0143 (8)	−0.0030 (7)	−0.0138 (7)
C18	0.0236 (8)	0.0181 (8)	0.0196 (7)	−0.0045 (6)	−0.0015 (6)	−0.0077 (6)
C19	0.0203 (8)	0.0159 (7)	0.0226 (8)	−0.0034 (6)	−0.0008 (6)	−0.0083 (6)
C20	0.0213 (8)	0.0157 (7)	0.0219 (7)	−0.0060 (6)	−0.0001 (6)	−0.0081 (6)
N3	0.0459 (10)	0.0221 (7)	0.0216 (7)	−0.0100 (7)	0.0049 (6)	−0.0102 (6)
N4	0.0252 (7)	0.0170 (6)	0.0209 (6)	−0.0058 (5)	0.0023 (5)	−0.0105 (5)
C51	0.0407 (10)	0.0203 (8)	0.0250 (8)	−0.0069 (7)	0.0040 (7)	−0.0117 (7)
C52	0.0348 (9)	0.0172 (8)	0.0227 (8)	−0.0068 (7)	0.0037 (7)	−0.0106 (6)
C53	0.0319 (9)	0.0151 (7)	0.0136 (7)	−0.0084 (6)	0.0025 (6)	−0.0066 (6)
C54	0.0379 (10)	0.0239 (8)	0.0187 (8)	−0.0128 (7)	0.0018 (7)	−0.0097 (7)
C55	0.0497 (12)	0.0240 (9)	0.0202 (8)	−0.0202 (8)	−0.0030 (8)	−0.0073 (7)
C56	0.0232 (8)	0.0147 (7)	0.0161 (7)	−0.0072 (6)	0.0025 (6)	−0.0070 (6)
C57	0.0218 (8)	0.0164 (7)	0.0199 (7)	−0.0016 (6)	−0.0016 (6)	−0.0091 (6)
C58	0.0232 (8)	0.0226 (8)	0.0206 (7)	−0.0050 (6)	−0.0013 (6)	−0.0119 (6)
C59	0.0210 (8)	0.0167 (7)	0.0206 (7)	−0.0011 (6)	0.0007 (6)	−0.0055 (6)
C60	0.0228 (8)	0.0212 (8)	0.0163 (7)	−0.0064 (6)	−0.0011 (6)	−0.0071 (6)
N1	0.0244 (7)	0.0171 (6)	0.0192 (6)	−0.0045 (5)	−0.0021 (5)	−0.0084 (5)
N2	0.0318 (8)	0.0188 (7)	0.0207 (7)	−0.0038 (6)	−0.0008 (6)	−0.0103 (6)
C41	0.0213 (8)	0.0167 (7)	0.0172 (7)	0.0001 (6)	−0.0022 (6)	−0.0069 (6)
C42	0.0173 (7)	0.0170 (7)	0.0169 (7)	−0.0022 (6)	−0.0033 (6)	−0.0065 (6)
C43	0.0197 (7)	0.0114 (7)	0.0137 (6)	−0.0031 (5)	−0.0012 (6)	−0.0039 (6)
C44	0.0176 (7)	0.0190 (8)	0.0199 (7)	−0.0029 (6)	−0.0005 (6)	−0.0079 (6)
C45	0.0208 (8)	0.0194 (8)	0.0231 (8)	−0.0077 (6)	−0.0027 (6)	−0.0094 (6)
C46	0.0208 (8)	0.0134 (7)	0.0149 (7)	−0.0040 (6)	0.0005 (6)	−0.0052 (6)
C47	0.0218 (8)	0.0161 (7)	0.0200 (7)	−0.0024 (6)	−0.0025 (6)	−0.0087 (6)
C48	0.0268 (8)	0.0211 (8)	0.0199 (7)	−0.0057 (6)	−0.0047 (6)	−0.0085 (6)
C49	0.0283 (9)	0.0194 (8)	0.0254 (8)	−0.0002 (6)	−0.0011 (7)	−0.0127 (7)
C50	0.0209 (8)	0.0200 (8)	0.0228 (8)	−0.0022 (6)	−0.0021 (6)	−0.0093 (6)
O5	0.0351 (7)	0.0303 (7)	0.0417 (8)	0.0097 (6)	−0.0099 (6)	−0.0182 (6)
O6	0.0357 (7)	0.0306 (7)	0.0362 (7)	−0.0051 (5)	−0.0105 (6)	−0.0207 (6)
C21	0.0805 (16)	0.0275 (10)	0.0270 (9)	−0.0202 (10)	0.0106 (10)	−0.0179 (8)
C22	0.0522 (11)	0.0165 (8)	0.0163 (7)	−0.0138 (7)	0.0065 (7)	−0.0087 (6)
C23	0.0367 (10)	0.0230 (9)	0.0261 (8)	−0.0089 (7)	0.0045 (7)	−0.0099 (7)
C24	0.0419 (10)	0.0285 (9)	0.0213 (8)	−0.0195 (8)	0.0013 (7)	−0.0105 (7)
C25	0.0426 (10)	0.0159 (8)	0.0219 (8)	−0.0110 (7)	0.0074 (7)	−0.0092 (7)
C26	0.0429 (11)	0.0231 (9)	0.0250 (9)	−0.0032 (7)	−0.0029 (8)	−0.0085 (7)
C27	0.0517 (12)	0.0258 (9)	0.0214 (8)	−0.0118 (8)	−0.0059 (8)	−0.0085 (7)
C28	0.0331 (9)	0.0207 (8)	0.0256 (8)	−0.0028 (7)	−0.0023 (7)	−0.0091 (7)
C29	0.0311 (9)	0.0229 (8)	0.0279 (8)	−0.0080 (7)	0.0003 (7)	−0.0145 (7)
C30	0.0285 (9)	0.0175 (8)	0.0193 (7)	−0.0051 (6)	−0.0016 (6)	−0.0097 (6)
O1	0.030 (4)	0.031 (2)	0.039 (2)	0.000 (3)	−0.004 (3)	−0.0259 (16)
O2	0.033 (4)	0.026 (2)	0.028 (3)	−0.001 (2)	−0.012 (2)	−0.0196 (15)
C1	0.075 (2)	0.0246 (10)	0.0271 (19)	−0.0159 (14)	0.0089 (16)	−0.0176 (11)
C5	0.013 (2)	0.0168 (19)	0.0147 (14)	−0.0075 (17)	−0.0060 (19)	−0.0038 (13)
C4	0.014 (2)	0.020 (2)	0.0213 (15)	0.0023 (16)	−0.0013 (18)	−0.0096 (15)
C3	0.033 (2)	0.017 (2)	0.023 (2)	−0.0029 (16)	0.0011 (18)	−0.0081 (15)
C2	0.0396 (10)	0.0161 (10)	0.0164 (9)	−0.0094 (7)	−0.0001 (7)	−0.0075 (6)
C7	0.027 (2)	0.024 (2)	0.017 (2)	−0.0136 (18)	−0.0057 (17)	−0.0058 (17)
C6	0.014 (2)	0.0167 (15)	0.0199 (17)	−0.0026 (18)	−0.0030 (19)	−0.0091 (13)
C8	0.0250 (16)	0.0141 (13)	0.0163 (13)	−0.0056 (12)	−0.0052 (11)	−0.0078 (11)
C9	0.0245 (18)	0.0163 (15)	0.0217 (15)	−0.0043 (12)	−0.0041 (13)	−0.0103 (12)
C10	0.022 (3)	0.0194 (18)	0.0172 (17)	−0.002 (2)	−0.007 (2)	−0.0097 (14)
O7	0.0273 (7)	0.0414 (8)	0.0390 (7)	0.0011 (5)	−0.0108 (5)	−0.0285 (6)
O8	0.0256 (6)	0.0283 (7)	0.0396 (7)	−0.0002 (5)	−0.0081 (5)	−0.0248 (6)
C31	0.0597 (13)	0.0220 (9)	0.0227 (8)	−0.0097 (8)	−0.0020 (8)	−0.0122 (7)
C32	0.0429 (10)	0.0158 (8)	0.0147 (7)	−0.0087 (7)	0.0016 (7)	−0.0060 (6)
C33	0.0358 (9)	0.0159 (8)	0.0232 (8)	−0.0038 (7)	0.0011 (7)	−0.0084 (6)
C34	0.0282 (9)	0.0193 (8)	0.0216 (8)	−0.0056 (6)	−0.0019 (6)	−0.0086 (6)
C35	0.0275 (8)	0.0159 (7)	0.0165 (7)	−0.0062 (6)	0.0003 (6)	−0.0068 (6)
C36	0.0312 (9)	0.0209 (8)	0.0193 (8)	−0.0020 (7)	−0.0036 (7)	−0.0091 (6)
C37	0.0385 (10)	0.0255 (9)	0.0187 (8)	−0.0078 (7)	−0.0053 (7)	−0.0104 (7)
C38	0.0267 (8)	0.0182 (8)	0.0179 (7)	−0.0060 (6)	−0.0036 (6)	−0.0073 (6)
C39	0.0270 (9)	0.0209 (8)	0.0217 (8)	−0.0057 (6)	−0.0050 (6)	−0.0106 (7)
C40	0.0237 (8)	0.0169 (7)	0.0182 (7)	−0.0040 (6)	−0.0018 (6)	−0.0077 (6)
O1A	0.019 (4)	0.030 (4)	0.029 (2)	−0.008 (3)	−0.003 (3)	−0.019 (2)
O2A	0.026 (2)	0.030 (2)	0.032 (2)	−0.0018 (16)	−0.0096 (17)	−0.0227 (15)
C1A	0.075 (2)	0.0246 (10)	0.0271 (19)	−0.0159 (14)	0.0089 (16)	−0.0176 (11)
C5A	0.014 (2)	0.0153 (16)	0.0136 (15)	−0.0044 (18)	−0.0013 (19)	−0.0067 (13)
C6A	0.017 (2)	0.0214 (18)	0.0227 (19)	−0.008 (2)	−0.003 (2)	−0.0093 (15)
C7A	0.034 (2)	0.020 (2)	0.021 (2)	−0.008 (2)	−0.003 (2)	−0.0136 (19)
C2A	0.0396 (10)	0.0161 (10)	0.0164 (9)	−0.0094 (7)	−0.0001 (7)	−0.0075 (6)
C3A	0.024 (2)	0.019 (3)	0.021 (2)	−0.0013 (17)	0.0023 (18)	−0.0083 (18)
C4A	0.009 (2)	0.017 (2)	0.0198 (18)	−0.0020 (19)	−0.005 (2)	−0.0075 (16)
C8A	0.0225 (19)	0.0149 (16)	0.0197 (16)	−0.0039 (14)	−0.0010 (14)	−0.0074 (13)
C9A	0.0221 (18)	0.0177 (15)	0.0212 (15)	−0.0021 (13)	−0.0042 (13)	−0.0098 (13)
C10A	0.018 (4)	0.0148 (18)	0.021 (3)	−0.006 (3)	−0.006 (3)	−0.0109 (19)

Geometric parameters (Å, º)

O3—C20	1.2144 (19)	C24—C25	1.397 (3)
O4—C20	1.3300 (19)	C25—C26	1.378 (3)
O4—H4	0.98 (3)	C25—C28	1.479 (2)
C11—H11A	0.9800	C26—H26	0.9500
C11—H11B	0.9800	C26—C27	1.373 (3)
C11—H11C	0.9800	C27—H27	0.9500
C11—C12	1.510 (2)	C28—H28	0.9500
C12—C13	1.398 (2)	C28—C29	1.313 (2)
C12—C17	1.383 (3)	C29—H29	0.9500
C13—H13	0.9500	C29—C30	1.474 (2)
C13—C14	1.388 (2)	O1—H1	0.8400
C14—H14	0.9500	O1—C10	1.332 (6)
C14—C15	1.402 (2)	O2—C10	1.215 (5)
C15—C16	1.393 (2)	C1—H1A	0.9800
C15—C18	1.470 (2)	C1—H1B	0.9800
C16—H16	0.9500	C1—H1C	0.9800
C16—C17	1.389 (2)	C1—C2	1.523 (5)
C17—H17	0.9500	C5—C4	1.3900
C18—H18	0.9500	C5—C6	1.3900
C18—C19	1.330 (2)	C5—C8	1.487 (4)
C19—H19	0.9500	C4—H4A	0.9500
C19—C20	1.482 (2)	C4—C3	1.3900
N3—C51	1.328 (2)	C3—H3	0.9500
N3—C55	1.329 (2)	C3—C2	1.3900
N4—C58	1.338 (2)	C2—C7	1.3900
N4—C59	1.335 (2)	C7—H7	0.9500
C51—H51	0.9500	C7—C6	1.3900
C51—C52	1.379 (2)	C6—H6A	0.9500
C52—H52	0.9500	C8—H8	0.9500
C52—C53	1.395 (2)	C8—C9	1.327 (4)
C53—C54	1.394 (2)	C9—H9	0.9500
C53—C56	1.482 (2)	C9—C10	1.472 (6)
C54—H54	0.9500	O7—C40	1.2132 (19)
C54—C55	1.402 (2)	O8—C40	1.3259 (19)
C55—H55	0.9500	O8—H8A	0.94 (3)
C56—C57	1.397 (2)	C31—H31A	0.9800
C56—C60	1.389 (2)	C31—H31B	0.9800
C57—H57	0.9500	C31—H31C	0.9800
C57—C58	1.379 (2)	C31—C32	1.510 (2)
C58—H58	0.9500	C32—C33	1.389 (2)
C59—H59	0.9500	C32—C37	1.393 (2)
C59—C60	1.384 (2)	C33—H33	0.9500
C60—H60	0.9500	C33—C34	1.388 (2)
N1—C41	1.339 (2)	C34—H34	0.9500
N1—C45	1.339 (2)	C34—C35	1.396 (2)
N2—C48	1.336 (2)	C35—C36	1.395 (2)
N2—C49	1.336 (2)	C35—C38	1.466 (2)
C41—H41	0.9500	C36—H36	0.9500
C41—C42	1.383 (2)	C36—C37	1.386 (2)
C42—H42	0.9500	C37—H37	0.9500
C42—C43	1.397 (2)	C38—H38	0.9500
C43—C44	1.395 (2)	C38—C39	1.331 (2)
C43—C46	1.481 (2)	C39—H39	0.9500
C44—H44	0.9500	C39—C40	1.475 (2)
C44—C45	1.381 (2)	O1A—H1AA	0.8400
C45—H45	0.9500	O1A—C10A	1.339 (6)
C46—C47	1.392 (2)	O2A—C10A	1.216 (6)
C46—C50	1.396 (2)	C1A—H1AB	0.9800
C47—H47	0.9500	C1A—H1AC	0.9800
C47—C48	1.387 (2)	C1A—H1AD	0.9800
C48—H48	0.9500	C1A—C2A	1.526 (6)
C49—H49	0.9500	C5A—C6A	1.3900
C49—C50	1.386 (2)	C5A—C4A	1.3900
C50—H50	0.9500	C5A—C8A	1.498 (5)
O5—C30	1.219 (2)	C6A—H6AA	0.9500
O6—C30	1.319 (2)	C6A—C7A	1.3900
O6—H6	1.002 (10)	C7A—H7A	0.9500
C21—H21A	0.9800	C7A—C2A	1.3900
C21—H21B	0.9800	C2A—C3A	1.3900
C21—H21C	0.9800	C3A—H3A	0.9500
C21—C22	1.508 (2)	C3A—C4A	1.3900
C22—C23	1.395 (3)	C4A—H4AA	0.9500
C22—C27	1.380 (3)	C8A—H8AA	0.9500
C23—H23	0.9500	C8A—C9A	1.328 (4)
C23—C24	1.396 (2)	C9A—H9A	0.9500
C24—H24	0.9500	C9A—C10A	1.477 (6)
C20—O4—H4	110.4 (15)	C25—C26—H26	119.4
H11A—C11—H11B	109.5	C27—C26—C25	121.12 (18)
H11A—C11—H11C	109.5	C27—C26—H26	119.4
H11B—C11—H11C	109.5	C22—C27—H27	119.1
C12—C11—H11A	109.5	C26—C27—C22	121.90 (18)
C12—C11—H11B	109.5	C26—C27—H27	119.1
C12—C11—H11C	109.5	C25—C28—H28	116.2
C13—C12—C11	120.90 (16)	C29—C28—C25	127.66 (17)
C17—C12—C11	121.24 (16)	C29—C28—H28	116.2
C17—C12—C13	117.87 (16)	C28—C29—H29	118.8
C12—C13—H13	119.4	C28—C29—C30	122.48 (17)
C14—C13—C12	121.15 (16)	C30—C29—H29	118.8
C14—C13—H13	119.4	O5—C30—O6	122.48 (15)
C13—C14—H14	119.7	O5—C30—C29	124.62 (16)
C13—C14—C15	120.62 (15)	O6—C30—C29	112.89 (14)
C15—C14—H14	119.7	C10—O1—H1	109.5
C14—C15—C18	122.92 (14)	H1A—C1—H1B	109.5
C16—C15—C14	118.01 (15)	H1A—C1—H1C	109.5
C16—C15—C18	119.02 (15)	H1B—C1—H1C	109.5
C15—C16—H16	119.6	C2—C1—H1A	109.5
C17—C16—C15	120.80 (16)	C2—C1—H1B	109.5
C17—C16—H16	119.6	C2—C1—H1C	109.5
C12—C17—C16	121.52 (16)	C4—C5—C6	120.0
C12—C17—H17	119.2	C4—C5—C8	118.7 (3)
C16—C17—H17	119.2	C6—C5—C8	121.3 (3)
C15—C18—H18	116.8	C5—C4—H4A	120.0
C19—C18—C15	126.31 (15)	C5—C4—C3	120.0
C19—C18—H18	116.8	C3—C4—H4A	120.0
C18—C19—H19	119.1	C4—C3—H3	120.0
C18—C19—C20	121.73 (15)	C2—C3—C4	120.0
C20—C19—H19	119.1	C2—C3—H3	120.0
O3—C20—O4	123.61 (15)	C3—C2—C1	117.4 (8)
O3—C20—C19	125.24 (15)	C3—C2—C7	120.0
O4—C20—C19	111.15 (13)	C7—C2—C1	122.6 (8)
C51—N3—C55	118.25 (16)	C2—C7—H7	120.0
C59—N4—C58	117.14 (14)	C6—C7—C2	120.0
N3—C51—H51	118.6	C6—C7—H7	120.0
N3—C51—C52	122.79 (17)	C5—C6—H6A	120.0
C52—C51—H51	118.6	C7—C6—C5	120.0
C51—C52—H52	120.0	C7—C6—H6A	120.0
C51—C52—C53	120.03 (17)	C5—C8—H8	116.6
C53—C52—H52	120.0	C9—C8—C5	126.7 (3)
C52—C53—C56	121.01 (15)	C9—C8—H8	116.6
C54—C53—C52	117.16 (15)	C8—C9—H9	118.7
C54—C53—C56	121.83 (15)	C8—C9—C10	122.6 (4)
C53—C54—H54	120.6	C10—C9—H9	118.7
C53—C54—C55	118.70 (17)	O1—C10—C9	110.6 (8)
C55—C54—H54	120.6	O2—C10—O1	123.9 (9)
N3—C55—C54	123.02 (17)	O2—C10—C9	125.6 (6)
N3—C55—H55	118.5	C40—O8—H8A	110.4 (16)
C54—C55—H55	118.5	H31A—C31—H31B	109.5
C57—C56—C53	120.79 (14)	H31A—C31—H31C	109.5
C60—C56—C53	121.82 (14)	H31B—C31—H31C	109.5
C60—C56—C57	117.38 (14)	C32—C31—H31A	109.5
C56—C57—H57	120.3	C32—C31—H31B	109.5
C58—C57—C56	119.42 (15)	C32—C31—H31C	109.5
C58—C57—H57	120.3	C33—C32—C31	121.32 (16)
N4—C58—C57	123.30 (15)	C33—C32—C37	117.92 (15)
N4—C58—H58	118.3	C37—C32—C31	120.76 (16)
C57—C58—H58	118.3	C32—C33—H33	119.6
N4—C59—H59	118.2	C34—C33—C32	120.84 (16)
N4—C59—C60	123.69 (15)	C34—C33—H33	119.6
C60—C59—H59	118.2	C33—C34—H34	119.4
C56—C60—H60	120.5	C33—C34—C35	121.25 (16)
C59—C60—C56	119.06 (15)	C35—C34—H34	119.4
C59—C60—H60	120.5	C34—C35—C38	119.70 (15)
C41—N1—C45	117.50 (14)	C36—C35—C34	117.90 (15)
C49—N2—C48	117.08 (14)	C36—C35—C38	122.39 (15)
N1—C41—H41	118.4	C35—C36—H36	119.7
N1—C41—C42	123.22 (14)	C37—C36—C35	120.51 (16)
C42—C41—H41	118.4	C37—C36—H36	119.7
C41—C42—H42	120.3	C32—C37—H37	119.2
C41—C42—C43	119.43 (14)	C36—C37—C32	121.56 (16)
C43—C42—H42	120.3	C36—C37—H37	119.2
C42—C43—C46	121.78 (14)	C35—C38—H38	116.5
C44—C43—C42	117.02 (14)	C39—C38—C35	126.96 (15)
C44—C43—C46	121.20 (14)	C39—C38—H38	116.5
C43—C44—H44	120.1	C38—C39—H39	118.9
C45—C44—C43	119.70 (14)	C38—C39—C40	122.11 (15)
C45—C44—H44	120.1	C40—C39—H39	118.9
N1—C45—C44	123.09 (14)	O7—C40—O8	122.89 (15)
N1—C45—H45	118.5	O7—C40—C39	124.70 (15)
C44—C45—H45	118.5	O8—C40—C39	112.39 (14)
C47—C46—C43	121.23 (13)	C10A—O1A—H1AA	109.5
C47—C46—C50	116.98 (14)	H1AB—C1A—H1AC	109.5
C50—C46—C43	121.79 (14)	H1AB—C1A—H1AD	109.5
C46—C47—H47	120.3	H1AC—C1A—H1AD	109.5
C48—C47—C46	119.36 (14)	C2A—C1A—H1AB	109.5
C48—C47—H47	120.3	C2A—C1A—H1AC	109.5
N2—C48—C47	123.63 (15)	C2A—C1A—H1AD	109.5
N2—C48—H48	118.2	C6A—C5A—C4A	120.0
C47—C48—H48	118.2	C6A—C5A—C8A	117.7 (3)
N2—C49—H49	118.3	C4A—C5A—C8A	122.3 (3)
N2—C49—C50	123.32 (15)	C5A—C6A—H6AA	120.0
C50—C49—H49	118.3	C7A—C6A—C5A	120.0
C46—C50—H50	120.2	C7A—C6A—H6AA	120.0
C49—C50—C46	119.61 (15)	C6A—C7A—H7A	120.0
C49—C50—H50	120.2	C6A—C7A—C2A	120.0
C30—O6—H6	110.2 (17)	C2A—C7A—H7A	120.0
H21A—C21—H21B	109.5	C7A—C2A—C1A	117.1 (9)
H21A—C21—H21C	109.5	C7A—C2A—C3A	120.0
H21B—C21—H21C	109.5	C3A—C2A—C1A	122.9 (9)
C22—C21—H21A	109.5	C2A—C3A—H3A	120.0
C22—C21—H21B	109.5	C4A—C3A—C2A	120.0
C22—C21—H21C	109.5	C4A—C3A—H3A	120.0
C23—C22—C21	120.94 (18)	C5A—C4A—H4AA	120.0
C27—C22—C21	121.15 (18)	C3A—C4A—C5A	120.0
C27—C22—C23	117.90 (16)	C3A—C4A—H4AA	120.0
C22—C23—H23	119.9	C5A—C8A—H8AA	116.8
C22—C23—C24	120.23 (17)	C9A—C8A—C5A	126.4 (4)
C24—C23—H23	119.9	C9A—C8A—H8AA	116.8
C23—C24—H24	119.6	C8A—C9A—H9A	116.9
C23—C24—C25	120.85 (17)	C8A—C9A—C10A	126.2 (4)
C25—C24—H24	119.6	C10A—C9A—H9A	116.9
C24—C25—C28	123.35 (16)	O1A—C10A—C9A	115.3 (7)
C26—C25—C24	117.98 (16)	O2A—C10A—O1A	122.3 (9)
C26—C25—C28	118.67 (17)	O2A—C10A—C9A	122.3 (6)
C11—C12—C13—C14	−179.92 (14)	C23—C22—C27—C26	1.2 (2)
C11—C12—C17—C16	−178.73 (15)	C23—C24—C25—C26	0.3 (2)
C12—C13—C14—C15	−1.7 (2)	C23—C24—C25—C28	−179.69 (15)
C13—C12—C17—C16	1.2 (2)	C24—C25—C26—C27	1.0 (2)
C13—C14—C15—C16	2.0 (2)	C24—C25—C28—C29	−7.2 (3)
C13—C14—C15—C18	−175.28 (14)	C25—C26—C27—C22	−1.8 (3)
C14—C15—C16—C17	−0.6 (2)	C25—C28—C29—C30	178.82 (15)
C14—C15—C18—C19	5.9 (2)	C26—C25—C28—C29	172.85 (17)
C15—C16—C17—C12	−1.0 (2)	C27—C22—C23—C24	0.1 (2)
C15—C18—C19—C20	174.67 (14)	C28—C25—C26—C27	−179.01 (16)
C16—C15—C18—C19	−171.36 (15)	C28—C29—C30—O5	7.4 (3)
C17—C12—C13—C14	0.1 (2)	C28—C29—C30—O6	−173.63 (15)
C18—C15—C16—C17	176.72 (14)	C1—C2—C7—C6	179.7 (12)
C18—C19—C20—O3	5.2 (2)	C5—C4—C3—C2	0.0
C18—C19—C20—O4	−173.75 (14)	C5—C8—C9—C10	179.3 (4)
N3—C51—C52—C53	−1.8 (2)	C4—C5—C6—C7	0.0
N4—C59—C60—C56	−0.6 (2)	C4—C5—C8—C9	179.6 (3)
C51—N3—C55—C54	−0.7 (2)	C4—C3—C2—C1	−179.7 (12)
C51—C52—C53—C54	−0.1 (2)	C4—C3—C2—C7	0.0
C51—C52—C53—C56	−179.87 (14)	C3—C2—C7—C6	0.0
C52—C53—C54—C55	1.6 (2)	C2—C7—C6—C5	0.0
C52—C53—C56—C57	−28.8 (2)	C6—C5—C4—C3	0.0
C52—C53—C56—C60	149.83 (15)	C6—C5—C8—C9	−1.6 (5)
C53—C54—C55—N3	−1.2 (2)	C8—C5—C4—C3	178.9 (4)
C53—C56—C57—C58	178.20 (14)	C8—C5—C6—C7	−178.8 (4)
C53—C56—C60—C59	−177.79 (13)	C8—C9—C10—O1	175.2 (8)
C54—C53—C56—C57	151.45 (15)	C8—C9—C10—O2	−6.4 (10)
C54—C53—C56—C60	−29.9 (2)	C31—C32—C33—C34	179.31 (15)
C55—N3—C51—C52	2.2 (2)	C31—C32—C37—C36	179.66 (15)
C56—C53—C54—C55	−178.71 (14)	C32—C33—C34—C35	0.6 (2)
C56—C57—C58—N4	−0.2 (2)	C33—C32—C37—C36	−1.1 (2)
C57—C56—C60—C59	0.9 (2)	C33—C34—C35—C36	−0.3 (2)
C58—N4—C59—C60	−0.1 (2)	C33—C34—C35—C38	179.50 (14)
C59—N4—C58—C57	0.6 (2)	C34—C35—C36—C37	−0.7 (2)
C60—C56—C57—C58	−0.5 (2)	C34—C35—C38—C39	176.68 (15)
N1—C41—C42—C43	1.4 (2)	C35—C36—C37—C32	1.4 (2)
N2—C49—C50—C46	−0.6 (2)	C35—C38—C39—C40	178.97 (14)
C41—N1—C45—C44	0.1 (2)	C36—C35—C38—C39	−3.6 (2)
C41—C42—C43—C44	0.1 (2)	C37—C32—C33—C34	0.0 (2)
C41—C42—C43—C46	−179.31 (13)	C38—C35—C36—C37	179.50 (14)
C42—C43—C44—C45	−1.5 (2)	C38—C39—C40—O7	−5.2 (2)
C42—C43—C46—C47	24.9 (2)	C38—C39—C40—O8	176.30 (14)
C42—C43—C46—C50	−156.08 (14)	C1A—C2A—C3A—C4A	−179.6 (14)
C43—C44—C45—N1	1.4 (2)	C5A—C6A—C7A—C2A	0.0
C43—C46—C47—C48	179.39 (13)	C5A—C8A—C9A—C10A	−176.8 (5)
C43—C46—C50—C49	−178.73 (14)	C6A—C5A—C4A—C3A	0.0
C44—C43—C46—C47	−154.49 (14)	C6A—C5A—C8A—C9A	175.4 (4)
C44—C43—C46—C50	24.5 (2)	C6A—C7A—C2A—C1A	179.6 (13)
C45—N1—C41—C42	−1.5 (2)	C6A—C7A—C2A—C3A	0.0
C46—C43—C44—C45	177.99 (13)	C7A—C2A—C3A—C4A	0.0
C46—C47—C48—N2	−0.8 (2)	C2A—C3A—C4A—C5A	0.0
C47—C46—C50—C49	0.3 (2)	C4A—C5A—C6A—C7A	0.0
C48—N2—C49—C50	0.2 (2)	C4A—C5A—C8A—C9A	−4.1 (5)
C49—N2—C48—C47	0.5 (2)	C8A—C5A—C6A—C7A	−179.5 (5)
C50—C46—C47—C48	0.4 (2)	C8A—C5A—C4A—C3A	179.5 (5)
C21—C22—C23—C24	−179.94 (15)	C8A—C9A—C10A—O1A	−6.4 (10)
C21—C22—C27—C26	−178.74 (16)	C8A—C9A—C10A—O2A	175.0 (7)
C22—C23—C24—C25	−0.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.84	1.82	2.631 (15)	161
O1A—H1AA···N2	0.84	1.98	2.793 (13)	164
O8—H8A···N1	0.94 (3)	1.70 (3)	2.6348 (18)	173 (2)
O4—H4···N4	0.98 (3)	1.69 (3)	2.6523 (17)	168 (2)
O6—H6···N3	1.00 (1)	1.66 (1)	2.6620 (19)	176 (3)

(2B)

Crystal data

C10H10O2·C6H6N2O	Z = 2
Mr = 284.31	F(000) = 300
Triclinic, P1	Dx = 1.347 Mg m^−3
a = 7.0311 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6172 (2) Å	Cell parameters from 7006 reflections
c = 11.9490 (3) Å	θ = 2.4–27.9°
α = 77.4101 (14)°	µ = 0.09 mm^−1
β = 87.9565 (14)°	T = 100 K
γ = 82.6358 (14)°	Block, colourless
V = 700.71 (3) Å^3	0.62 × 0.35 × 0.28 mm

Data collection

Bruker Apex II kappa CCD area detector diffractometer	3359 independent reflections
Radiation source: fine-focus sealed tube	3003 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 27.9°, θmin = 1.8°
Absorption correction: multi-scan SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0519 before and 0.0308 after correction. The Ratio of minimum to maximum transmission is 0.8911. The λ/2 correction factor is 0.00150.	h = −9→9
Tmin = 0.664, Tmax = 0.746	k = −11→11
12831 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: iterative
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) = 0.101	w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 0.208P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3359 reflections	Δρmax = 0.44 e Å^−3
203 parameters	Δρmin = −0.19 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.05520 (11)	0.34107 (9)	0.71195 (7)	0.02597 (19)
O2	0.26553 (11)	0.12123 (9)	0.72318 (7)	0.02395 (18)
C1	0.41978 (15)	0.72320 (12)	0.86360 (9)	0.0196 (2)
H1	0.2886	0.7657	0.8527	0.024*
C2	0.54497 (16)	0.81057 (13)	0.90387 (9)	0.0213 (2)
H2A	0.4983	0.9119	0.9201	0.026*
C3	0.73744 (15)	0.75164 (13)	0.92074 (8)	0.0197 (2)
C4	0.80196 (14)	0.60304 (13)	0.89522 (9)	0.0196 (2)
H4	0.9335	0.5614	0.9055	0.024*
C5	0.67786 (15)	0.51482 (12)	0.85509 (8)	0.0182 (2)
H5	0.7252	0.4139	0.8386	0.022*
C6	0.48375 (14)	0.57342 (11)	0.83875 (8)	0.0164 (2)
C7	0.34499 (14)	0.48712 (12)	0.79657 (8)	0.0168 (2)
H7	0.2186	0.5414	0.7845	0.020*
C8	0.37443 (14)	0.34154 (12)	0.77306 (9)	0.0180 (2)
H8	0.4987	0.2826	0.7824	0.022*
C9	0.21579 (14)	0.27070 (11)	0.73264 (8)	0.0163 (2)
C10	0.87403 (17)	0.84688 (14)	0.96386 (10)	0.0260 (2)
H10A	0.9338	0.9136	0.8985	0.039*
H10B	0.9736	0.7733	1.0103	0.039*
H10C	0.8033	0.9154	1.0108	0.039*
O3	−0.50814 (10)	−0.29014 (8)	0.51462 (7)	0.02044 (17)
N1	0.00113 (12)	−0.02390 (10)	0.65420 (7)	0.01741 (18)
N2	−0.27498 (12)	−0.49794 (10)	0.56946 (8)	0.01714 (18)
C11	0.08154 (14)	−0.15978 (12)	0.62572 (8)	0.0172 (2)
H11	0.2173	−0.1828	0.6269	0.021*
C12	−0.02469 (14)	−0.26806 (11)	0.59461 (8)	0.0162 (2)
H12	0.0370	−0.3642	0.5763	0.019*
C13	−0.22341 (13)	−0.23357 (11)	0.59063 (8)	0.01402 (19)
C14	−0.30763 (14)	−0.09026 (11)	0.61693 (8)	0.0162 (2)
H14	−0.4427	−0.0616	0.6128	0.019*
C15	−0.19011 (15)	0.00962 (11)	0.64918 (9)	0.0179 (2)
H15	−0.2478	0.1062	0.6686	0.021*
C16	−0.34835 (13)	−0.34414 (11)	0.55557 (8)	0.01457 (19)
H2B	−0.166 (2)	−0.5365 (17)	0.6088 (12)	0.025 (3)*
H2C	−0.348 (2)	−0.5673 (17)	0.5473 (12)	0.027 (3)*
H2	0.157 (3)	0.082 (2)	0.6946 (16)	0.059 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0193 (4)	0.0201 (4)	0.0391 (5)	0.0010 (3)	−0.0109 (3)	−0.0082 (3)
O2	0.0180 (4)	0.0173 (4)	0.0394 (5)	−0.0015 (3)	−0.0068 (3)	−0.0118 (3)
C1	0.0169 (5)	0.0210 (5)	0.0221 (5)	−0.0019 (4)	−0.0012 (4)	−0.0072 (4)
C2	0.0247 (5)	0.0198 (5)	0.0217 (5)	−0.0040 (4)	0.0000 (4)	−0.0091 (4)
C3	0.0221 (5)	0.0242 (5)	0.0146 (4)	−0.0090 (4)	−0.0007 (4)	−0.0047 (4)
C4	0.0163 (5)	0.0248 (5)	0.0177 (5)	−0.0037 (4)	−0.0021 (4)	−0.0032 (4)
C5	0.0195 (5)	0.0173 (4)	0.0180 (4)	−0.0020 (4)	−0.0013 (4)	−0.0041 (4)
C6	0.0180 (5)	0.0176 (5)	0.0145 (4)	−0.0044 (4)	−0.0010 (4)	−0.0037 (4)
C7	0.0151 (4)	0.0177 (4)	0.0177 (4)	−0.0024 (3)	−0.0024 (3)	−0.0035 (4)
C8	0.0144 (4)	0.0183 (5)	0.0218 (5)	−0.0022 (3)	−0.0030 (4)	−0.0050 (4)
C9	0.0171 (4)	0.0150 (4)	0.0170 (4)	−0.0029 (3)	−0.0014 (3)	−0.0029 (3)
C10	0.0263 (6)	0.0314 (6)	0.0248 (5)	−0.0126 (4)	−0.0019 (4)	−0.0104 (4)
O3	0.0157 (3)	0.0170 (3)	0.0296 (4)	−0.0006 (3)	−0.0075 (3)	−0.0066 (3)
N1	0.0191 (4)	0.0153 (4)	0.0186 (4)	−0.0048 (3)	−0.0028 (3)	−0.0035 (3)
N2	0.0136 (4)	0.0151 (4)	0.0241 (4)	−0.0012 (3)	−0.0048 (3)	−0.0068 (3)
C11	0.0136 (4)	0.0179 (4)	0.0205 (5)	−0.0035 (3)	−0.0012 (3)	−0.0041 (4)
C12	0.0152 (4)	0.0150 (4)	0.0193 (5)	−0.0017 (3)	−0.0004 (3)	−0.0058 (3)
C13	0.0144 (4)	0.0138 (4)	0.0142 (4)	−0.0035 (3)	−0.0012 (3)	−0.0026 (3)
C14	0.0143 (4)	0.0152 (4)	0.0189 (5)	−0.0014 (3)	−0.0012 (3)	−0.0035 (4)
C15	0.0202 (5)	0.0131 (4)	0.0210 (5)	−0.0012 (3)	−0.0017 (4)	−0.0052 (4)
C16	0.0133 (4)	0.0159 (4)	0.0156 (4)	−0.0034 (3)	−0.0003 (3)	−0.0048 (3)

Geometric parameters (Å, º)

O1—C9	1.2177 (12)	C10—H10A	0.9800
O2—C9	1.3188 (12)	C10—H10B	0.9800
O2—H2	0.97 (2)	C10—H10C	0.9800
C1—H1	0.9500	O3—C16	1.2346 (12)
C1—C2	1.3897 (14)	N1—C11	1.3404 (13)
C1—C6	1.4018 (13)	N1—C15	1.3393 (13)
C2—H2A	0.9500	N2—C16	1.3361 (12)
C2—C3	1.3887 (15)	N2—H2B	0.898 (15)
C3—C4	1.3964 (15)	N2—H2C	0.920 (15)
C3—C10	1.5110 (14)	C11—H11	0.9500
C4—H4	0.9500	C11—C12	1.3843 (13)
C4—C5	1.3886 (14)	C12—H12	0.9500
C5—H5	0.9500	C12—C13	1.3910 (13)
C5—C6	1.3982 (14)	C13—C14	1.3939 (13)
C6—C7	1.4640 (13)	C13—C16	1.5066 (12)
C7—H7	0.9500	C14—H14	0.9500
C7—C8	1.3336 (14)	C14—C15	1.3862 (13)
C8—H8	0.9500	C15—H15	0.9500
C8—C9	1.4804 (13)
C9—O2—H2	109.3 (11)	C3—C10—H10A	109.5
C2—C1—H1	119.4	C3—C10—H10B	109.5
C2—C1—C6	121.11 (9)	C3—C10—H10C	109.5
C6—C1—H1	119.4	H10A—C10—H10B	109.5
C1—C2—H2A	119.6	H10A—C10—H10C	109.5
C3—C2—C1	120.81 (9)	H10B—C10—H10C	109.5
C3—C2—H2A	119.6	C15—N1—C11	118.12 (8)
C2—C3—C4	118.22 (9)	C16—N2—H2B	121.4 (9)
C2—C3—C10	120.89 (10)	C16—N2—H2C	118.1 (9)
C4—C3—C10	120.88 (10)	H2B—N2—H2C	119.9 (12)
C3—C4—H4	119.3	N1—C11—H11	118.6
C5—C4—C3	121.36 (9)	N1—C11—C12	122.86 (9)
C5—C4—H4	119.3	C12—C11—H11	118.6
C4—C5—H5	119.7	C11—C12—H12	120.6
C4—C5—C6	120.52 (9)	C11—C12—C13	118.81 (9)
C6—C5—H5	119.7	C13—C12—H12	120.6
C1—C6—C7	118.56 (9)	C12—C13—C14	118.61 (9)
C5—C6—C1	117.97 (9)	C12—C13—C16	121.87 (8)
C5—C6—C7	123.47 (9)	C14—C13—C16	119.49 (8)
C6—C7—H7	116.1	C13—C14—H14	120.7
C8—C7—C6	127.89 (9)	C15—C14—C13	118.57 (9)
C8—C7—H7	116.1	C15—C14—H14	120.7
C7—C8—H8	119.6	N1—C15—C14	122.98 (9)
C7—C8—C9	120.80 (9)	N1—C15—H15	118.5
C9—C8—H8	119.6	C14—C15—H15	118.5
O1—C9—O2	123.16 (9)	O3—C16—N2	123.62 (9)
O1—C9—C8	124.02 (9)	O3—C16—C13	119.81 (8)
O2—C9—C8	112.80 (8)	N2—C16—C13	116.56 (8)
C1—C2—C3—C4	0.55 (15)	C10—C3—C4—C5	−179.73 (9)
C1—C2—C3—C10	179.64 (10)	N1—C11—C12—C13	1.18 (15)
C1—C6—C7—C8	−176.74 (10)	C11—N1—C15—C14	0.56 (15)
C2—C1—C6—C5	−0.36 (15)	C11—C12—C13—C14	0.71 (14)
C2—C1—C6—C7	−179.99 (9)	C11—C12—C13—C16	178.92 (9)
C2—C3—C4—C5	−0.63 (15)	C12—C13—C14—C15	−1.85 (14)
C3—C4—C5—C6	0.22 (15)	C12—C13—C16—O3	−154.72 (10)
C4—C5—C6—C1	0.28 (14)	C12—C13—C16—N2	24.08 (13)
C4—C5—C6—C7	179.89 (9)	C13—C14—C15—N1	1.26 (15)
C5—C6—C7—C8	3.65 (16)	C14—C13—C16—O3	23.48 (14)
C6—C1—C2—C3	−0.06 (16)	C14—C13—C16—N2	−157.72 (9)
C6—C7—C8—C9	178.93 (9)	C15—N1—C11—C12	−1.81 (15)
C7—C8—C9—O1	4.44 (16)	C16—C13—C14—C15	179.89 (8)
C7—C8—C9—O2	−174.40 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1^i	0.898 (15)	2.052 (15)	2.9393 (11)	169.5 (12)
N2—H2C···O3^ii	0.920 (15)	1.962 (15)	2.8796 (11)	174.4 (12)
O2—H2···N1	0.97 (2)	1.66 (2)	2.6179 (11)	167.6 (17)

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

(3A)

Crystal data

2(C10H10O3)·C10H8N2	F(000) = 540
Mr = 512.54	Dx = 1.357 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.4681 (3) Å	Cell parameters from 9027 reflections
b = 28.9773 (13) Å	θ = 2.8–28.0°
c = 6.8930 (3) Å	µ = 0.10 mm^−1
β = 103.812 (2)°	T = 100 K
V = 1254.58 (10) Å^3	Block, colourless
Z = 2	0.4 × 0.35 × 0.35 mm

Data collection

Bruker Apex II kappa CCD area detector diffractometer	3014 independent reflections
Radiation source: fine-focus sealed tube	2677 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 28.0°, θmin = 1.4°
Absorption correction: multi-scan SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0640 before and 0.0469 after correction. The Ratio of minimum to maximum transmission is 0.8542. The λ/2 correction factor is 0.00150.	h = −8→8
Tmin = 0.637, Tmax = 0.746	k = −38→38
22702 measured reflections	l = −8→9

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0454P)^2 + 0.7676P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3014 reflections	Δρmax = 0.35 e Å^−3
177 parameters	Δρmin = −0.25 e Å^−3
0 restraints

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.63845 (14)	0.59800 (3)	0.24671 (14)	0.0173 (2)
H1	0.625 (3)	0.5807 (7)	0.360 (3)	0.041 (5)*
O2	0.95668 (15)	0.56268 (3)	0.31698 (14)	0.0198 (2)
O3	1.28947 (15)	0.71831 (3)	−0.60950 (14)	0.0194 (2)
C1	0.9835 (2)	0.65254 (4)	−0.33031 (19)	0.0159 (3)
H1A	0.8460	0.6390	−0.3545	0.019*
C2	1.0443 (2)	0.67604 (4)	−0.48229 (19)	0.0157 (3)
H2	0.9486	0.6785	−0.6099	0.019*
C3	1.2463 (2)	0.69620 (4)	−0.44864 (19)	0.0153 (3)
C4	1.3868 (2)	0.69284 (4)	−0.2619 (2)	0.0167 (3)
H4	1.5236	0.7067	−0.2379	0.020*
C5	1.3238 (2)	0.66873 (4)	−0.11025 (19)	0.0157 (3)
H5	1.4204	0.6660	0.0168	0.019*
C6	1.12277 (19)	0.64853 (4)	−0.14035 (18)	0.0139 (2)
C7	1.0645 (2)	0.62373 (4)	0.02436 (19)	0.0149 (2)
H7	1.1776	0.6140	0.1316	0.018*
C8	0.8666 (2)	0.61353 (4)	0.03733 (18)	0.0152 (2)
H8	0.7492	0.6224	−0.0675	0.018*
C9	0.82758 (19)	0.58853 (4)	0.21323 (18)	0.0140 (2)
C10	1.5014 (2)	0.73485 (6)	−0.5891 (2)	0.0281 (3)
H10A	1.5343	0.7579	−0.4819	0.042*
H10B	1.5139	0.7490	−0.7149	0.042*
H10C	1.6016	0.7090	−0.5563	0.042*
N1	0.58525 (17)	0.55709 (4)	0.56938 (15)	0.0142 (2)
C11	0.7275 (2)	0.52673 (4)	0.67042 (19)	0.0155 (3)
H11	0.8523	0.5208	0.6247	0.019*
C12	0.70005 (19)	0.50366 (4)	0.83861 (19)	0.0148 (2)
H12	0.8048	0.4824	0.9058	0.018*
C13	0.51781 (19)	0.51174 (4)	0.90919 (17)	0.0121 (2)
C14	0.3697 (2)	0.54296 (4)	0.80114 (19)	0.0154 (3)
H14	0.2423	0.5493	0.8419	0.018*
C15	0.4087 (2)	0.56472 (4)	0.63439 (19)	0.0159 (3)
H15	0.3062	0.5859	0.5632	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0145 (4)	0.0239 (5)	0.0149 (4)	0.0020 (3)	0.0060 (3)	0.0058 (4)
O2	0.0180 (5)	0.0228 (5)	0.0195 (5)	0.0038 (4)	0.0064 (4)	0.0065 (4)
O3	0.0170 (5)	0.0251 (5)	0.0173 (5)	−0.0015 (4)	0.0068 (4)	0.0070 (4)
C1	0.0146 (6)	0.0182 (6)	0.0154 (6)	−0.0022 (4)	0.0047 (5)	−0.0012 (5)
C2	0.0157 (6)	0.0196 (6)	0.0119 (6)	0.0000 (5)	0.0034 (5)	−0.0008 (4)
C3	0.0179 (6)	0.0148 (6)	0.0153 (6)	0.0012 (4)	0.0082 (5)	0.0019 (4)
C4	0.0127 (6)	0.0187 (6)	0.0191 (6)	−0.0011 (4)	0.0044 (5)	0.0021 (5)
C5	0.0133 (6)	0.0188 (6)	0.0148 (6)	0.0012 (4)	0.0033 (5)	0.0018 (4)
C6	0.0153 (6)	0.0140 (5)	0.0138 (6)	0.0008 (4)	0.0064 (5)	0.0002 (4)
C7	0.0171 (6)	0.0153 (5)	0.0132 (6)	0.0010 (4)	0.0053 (5)	0.0009 (4)
C8	0.0163 (6)	0.0175 (6)	0.0123 (6)	0.0007 (4)	0.0045 (5)	0.0013 (4)
C9	0.0144 (6)	0.0159 (5)	0.0120 (5)	−0.0022 (4)	0.0040 (4)	−0.0014 (4)
C10	0.0204 (7)	0.0370 (8)	0.0283 (8)	−0.0067 (6)	0.0083 (6)	0.0135 (6)
N1	0.0150 (5)	0.0164 (5)	0.0113 (5)	−0.0024 (4)	0.0034 (4)	−0.0002 (4)
C11	0.0138 (6)	0.0184 (6)	0.0155 (6)	−0.0010 (4)	0.0059 (5)	−0.0005 (5)
C12	0.0134 (6)	0.0166 (6)	0.0147 (6)	0.0014 (4)	0.0042 (5)	0.0012 (4)
C13	0.0135 (5)	0.0134 (5)	0.0099 (6)	−0.0022 (4)	0.0036 (4)	−0.0010 (4)
C14	0.0141 (6)	0.0187 (6)	0.0147 (6)	0.0019 (4)	0.0059 (5)	0.0014 (5)
C15	0.0152 (6)	0.0184 (6)	0.0138 (6)	0.0018 (4)	0.0028 (5)	0.0030 (5)

Geometric parameters (Å, º)

O1—H1	0.95 (2)	C7—C8	1.3373 (17)
O1—C9	1.3266 (15)	C8—H8	0.9500
O2—C9	1.2184 (15)	C8—C9	1.4848 (17)
O3—C3	1.3659 (15)	C10—H10A	0.9800
O3—C10	1.4273 (16)	C10—H10B	0.9800
C1—H1A	0.9500	C10—H10C	0.9800
C1—C2	1.3831 (17)	N1—C11	1.3414 (16)
C1—C6	1.4059 (17)	N1—C15	1.3407 (16)
C2—H2	0.9500	C11—H11	0.9500
C2—C3	1.3993 (17)	C11—C12	1.3858 (17)
C3—C4	1.3906 (18)	C12—H12	0.9500
C4—H4	0.9500	C12—C13	1.3981 (16)
C4—C5	1.3965 (17)	C13—C13^i	1.490 (2)
C5—H5	0.9500	C13—C14	1.3964 (16)
C5—C6	1.3959 (17)	C14—H14	0.9500
C6—C7	1.4669 (16)	C14—C15	1.3860 (17)
C7—H7	0.9500	C15—H15	0.9500
C9—O1—H1	107.6 (12)	O1—C9—C8	112.62 (10)
C3—O3—C10	117.07 (10)	O2—C9—O1	123.80 (11)
C2—C1—H1A	119.6	O2—C9—C8	123.58 (11)
C2—C1—C6	120.74 (12)	O3—C10—H10A	109.5
C6—C1—H1A	119.6	O3—C10—H10B	109.5
C1—C2—H2	119.9	O3—C10—H10C	109.5
C1—C2—C3	120.21 (12)	H10A—C10—H10B	109.5
C3—C2—H2	119.9	H10A—C10—H10C	109.5
O3—C3—C2	115.15 (11)	H10B—C10—H10C	109.5
O3—C3—C4	124.69 (11)	C15—N1—C11	117.89 (11)
C4—C3—C2	120.16 (11)	N1—C11—H11	118.6
C3—C4—H4	120.5	N1—C11—C12	122.80 (11)
C3—C4—C5	119.00 (12)	C12—C11—H11	118.6
C5—C4—H4	120.5	C11—C12—H12	120.1
C4—C5—H5	119.1	C11—C12—C13	119.82 (11)
C6—C5—C4	121.78 (12)	C13—C12—H12	120.1
C6—C5—H5	119.1	C12—C13—C13^i	121.87 (13)
C1—C6—C7	122.36 (11)	C14—C13—C12	116.80 (11)
C5—C6—C1	118.10 (11)	C14—C13—C13^i	121.33 (13)
C5—C6—C7	119.54 (11)	C13—C14—H14	120.0
C6—C7—H7	117.0	C15—C14—C13	119.95 (11)
C8—C7—C6	125.94 (12)	C15—C14—H14	120.0
C8—C7—H7	117.0	N1—C15—C14	122.72 (11)
C7—C8—H8	119.5	N1—C15—H15	118.6
C7—C8—C9	120.95 (11)	C14—C15—H15	118.6
C9—C8—H8	119.5
O3—C3—C4—C5	−179.26 (11)	C7—C8—C9—O1	152.98 (12)
C1—C2—C3—O3	179.70 (11)	C7—C8—C9—O2	−26.01 (19)
C1—C2—C3—C4	−0.23 (19)	C10—O3—C3—C2	−173.13 (12)
C1—C6—C7—C8	−19.52 (19)	C10—O3—C3—C4	6.79 (19)
C2—C1—C6—C5	−0.28 (18)	N1—C11—C12—C13	−0.01 (19)
C2—C1—C6—C7	−179.75 (11)	C11—N1—C15—C14	0.64 (19)
C2—C3—C4—C5	0.67 (19)	C11—C12—C13—C13^i	−179.23 (13)
C3—C4—C5—C6	−0.93 (19)	C11—C12—C13—C14	0.83 (18)
C4—C5—C6—C1	0.73 (18)	C12—C13—C14—C15	−0.92 (18)
C4—C5—C6—C7	−179.78 (11)	C13^i—C13—C14—C15	179.14 (13)
C5—C6—C7—C8	161.02 (13)	C13—C14—C15—N1	0.20 (19)
C6—C1—C2—C3	0.03 (19)	C15—N1—C11—C12	−0.73 (18)
C6—C7—C8—C9	−179.45 (11)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.95 (2)	1.67 (2)	2.6146 (14)	171.7 (19)

(3B)

Crystal data

C10H10O3·C6H6N2O	Z = 4
Mr = 300.31	F(000) = 632
Triclinic, P1	Dx = 1.375 Mg m^−3
a = 9.1225 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5523 (4) Å	Cell parameters from 3066 reflections
c = 14.1938 (5) Å	θ = 2.3–26.7°
α = 90.700 (3)°	µ = 0.10 mm^−1
β = 90.577 (3)°	T = 100 K
γ = 104.055 (3)°	Plate, colourless
V = 1450.81 (10) Å^3	0.35 × 0.2 × 0.13 mm

Data collection

Bruker Apex II kappa CCD area detector diffractometer	6900 independent reflections
Radiation source: fine-focus sealed tube	4151 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
φ and ω scans	θmax = 27.9°, θmin = 1.4°
Absorption correction: multi-scan SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0847 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.7516. The λ/2 correction factor is 0.00150.	h = −11→11
Tmin = 0.560, Tmax = 0.746	k = −14→15
26528 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: iterative
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) = 0.141	w = 1/[σ^2(Fo^2) + (0.0671P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
6900 reflections	Δρmax = 0.39 e Å^−3
423 parameters	Δρmin = −0.32 e Å^−3
1 restraint

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.94504 (17)	0.70436 (12)	0.74323 (10)	0.0249 (4)
O2	1.06773 (17)	0.73328 (12)	0.88217 (10)	0.0266 (4)
O3	1.36930 (16)	1.36989 (11)	0.52557 (10)	0.0218 (3)
C1	1.2618 (2)	1.13587 (16)	0.69677 (14)	0.0177 (4)
H1A	1.2721	1.1276	0.7628	0.021*
C2	1.3192 (2)	1.24499 (16)	0.65587 (13)	0.0169 (4)
H2	1.3677	1.3116	0.6941	0.020*
C3	1.3067 (2)	1.25827 (16)	0.55895 (14)	0.0159 (4)
C4	1.2367 (2)	1.16154 (16)	0.50205 (14)	0.0168 (4)
H4	1.2290	1.1697	0.4358	0.020*
C5	1.1779 (2)	1.05210 (16)	0.54456 (14)	0.0161 (4)
H5	1.1292	0.9856	0.5062	0.019*
C6	1.1882 (2)	1.03710 (16)	0.64134 (13)	0.0159 (4)
C7	1.1171 (2)	0.92078 (16)	0.68089 (14)	0.0174 (4)
H7	1.0602	0.8626	0.6382	0.021*
C8	1.1233 (2)	0.88745 (17)	0.77000 (15)	0.0216 (5)
H8	1.1816	0.9430	0.8140	0.026*
C9	1.0446 (2)	0.76920 (17)	0.80376 (15)	0.0203 (5)
C10	1.3537 (3)	1.38724 (19)	0.42663 (15)	0.0301 (5)
H10A	1.4003	1.3323	0.3914	0.045*
H10B	1.4039	1.4697	0.4112	0.045*
H10C	1.2462	1.3716	0.4096	0.045*
O5	0.42311 (17)	0.72240 (12)	0.75801 (10)	0.0242 (3)
O6	0.59436 (18)	0.72282 (13)	0.87104 (11)	0.0329 (4)
O7	0.90562 (16)	1.35110 (12)	0.50917 (10)	0.0255 (4)
C17	0.8216 (2)	1.10867 (16)	0.67391 (14)	0.0176 (4)
H17	0.8735	1.0777	0.7221	0.021*
C18	0.8963 (2)	1.20710 (16)	0.62481 (14)	0.0189 (4)
H18	0.9994	1.2432	0.6389	0.023*
C19	0.8206 (2)	1.25416 (16)	0.55419 (14)	0.0184 (4)
C20	0.6698 (2)	1.20228 (17)	0.53402 (14)	0.0187 (4)
H20	0.6176	1.2343	0.4866	0.022*
C21	0.5958 (2)	1.10291 (16)	0.58396 (13)	0.0179 (4)
H21	0.4923	1.0677	0.5703	0.021*
C22	0.6696 (2)	1.05360 (16)	0.65349 (13)	0.0165 (4)
C23	0.5864 (2)	0.94426 (16)	0.69885 (14)	0.0191 (4)
H23	0.4848	0.9130	0.6785	0.023*
C24	0.6387 (2)	0.88436 (17)	0.76561 (15)	0.0233 (5)
H24	0.7378	0.9165	0.7900	0.028*
C25	0.5510 (2)	0.77095 (18)	0.80366 (15)	0.0220 (5)
C26	0.8349 (3)	1.39813 (18)	0.43274 (16)	0.0295 (5)
H26A	0.7479	1.4251	0.4562	0.044*
H26B	0.8007	1.3358	0.3844	0.044*
H26C	0.9076	1.4656	0.4054	0.044*
O8	0.48129 (16)	0.09885 (12)	0.90149 (10)	0.0239 (3)
N3	0.80355 (19)	0.49635 (14)	0.81641 (12)	0.0190 (4)
N4	0.6599 (2)	0.12747 (16)	1.01753 (13)	0.0236 (4)
C27	0.8204 (2)	0.48051 (17)	0.90900 (14)	0.0196 (4)
H27	0.8774	0.5452	0.9461	0.024*
C28	0.7580 (2)	0.37337 (17)	0.95269 (14)	0.0184 (4)
H28	0.7729	0.3650	1.0184	0.022*
C29	0.6734 (2)	0.27851 (16)	0.89934 (14)	0.0163 (4)
C30	0.6534 (2)	0.29554 (17)	0.80361 (14)	0.0180 (4)
H30	0.5940	0.2333	0.7653	0.022*
C31	0.7215 (2)	0.40463 (17)	0.76518 (14)	0.0192 (4)
H31	0.7095	0.4150	0.6995	0.023*
C32	0.5974 (2)	0.15963 (16)	0.94018 (14)	0.0180 (4)
O4	−0.01705 (17)	0.10018 (12)	0.89954 (10)	0.0268 (4)
N1	0.29592 (19)	0.50607 (14)	0.82447 (12)	0.0185 (4)
N2	0.1633 (2)	0.12536 (17)	1.01373 (13)	0.0236 (4)
C11	0.3769 (2)	0.45340 (16)	0.88117 (14)	0.0179 (4)
H11	0.4789	0.4936	0.8948	0.022*
C12	0.3199 (2)	0.34324 (16)	0.92101 (14)	0.0176 (4)
H12	0.3813	0.3093	0.9614	0.021*
C13	0.1714 (2)	0.28303 (16)	0.90097 (13)	0.0171 (4)
C14	0.0869 (2)	0.33565 (17)	0.84071 (13)	0.0185 (4)
H14	−0.0143	0.2963	0.8244	0.022*
C15	0.1533 (2)	0.44700 (17)	0.80482 (14)	0.0196 (4)
H15	0.0946	0.4832	0.7642	0.024*
C16	0.0974 (2)	0.16060 (16)	0.93908 (14)	0.0176 (4)
H4A	0.617 (3)	0.054 (2)	1.0475 (19)	0.053 (8)*
H2A	0.120 (3)	0.048 (2)	1.0384 (18)	0.045 (7)*
H1	0.894 (3)	0.628 (2)	0.7742 (19)	0.069 (9)*
H5A	0.376 (3)	0.644 (2)	0.7878 (18)	0.061 (9)*
H4B	0.749 (3)	0.173 (2)	1.0425 (19)	0.059 (9)*
H2B	0.242 (3)	0.174 (2)	1.0441 (18)	0.050 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0288 (9)	0.0191 (8)	0.0196 (8)	−0.0079 (7)	−0.0076 (7)	0.0050 (6)
O2	0.0304 (9)	0.0217 (8)	0.0220 (9)	−0.0044 (7)	−0.0088 (7)	0.0076 (6)
O3	0.0258 (8)	0.0155 (7)	0.0199 (8)	−0.0031 (6)	−0.0047 (6)	0.0054 (6)
C1	0.0187 (10)	0.0195 (10)	0.0141 (10)	0.0033 (8)	−0.0023 (8)	0.0006 (8)
C2	0.0187 (10)	0.0154 (9)	0.0158 (10)	0.0031 (8)	−0.0044 (8)	−0.0020 (8)
C3	0.0151 (10)	0.0143 (10)	0.0175 (11)	0.0016 (8)	−0.0020 (8)	0.0042 (8)
C4	0.0171 (10)	0.0186 (10)	0.0137 (10)	0.0024 (8)	−0.0025 (8)	0.0002 (8)
C5	0.0141 (9)	0.0155 (9)	0.0177 (11)	0.0021 (8)	−0.0052 (8)	−0.0025 (8)
C6	0.0144 (10)	0.0148 (9)	0.0177 (11)	0.0023 (8)	−0.0024 (8)	0.0008 (8)
C7	0.0169 (10)	0.0145 (9)	0.0191 (11)	0.0007 (8)	−0.0031 (8)	−0.0002 (8)
C8	0.0232 (11)	0.0171 (10)	0.0204 (12)	−0.0028 (9)	−0.0053 (9)	0.0016 (9)
C9	0.0219 (11)	0.0185 (10)	0.0185 (11)	0.0009 (9)	−0.0045 (9)	0.0016 (9)
C10	0.0383 (14)	0.0242 (12)	0.0214 (12)	−0.0047 (10)	−0.0082 (10)	0.0109 (10)
O5	0.0245 (8)	0.0194 (8)	0.0235 (8)	−0.0047 (6)	−0.0085 (6)	0.0067 (6)
O6	0.0337 (10)	0.0285 (9)	0.0291 (9)	−0.0069 (7)	−0.0147 (7)	0.0114 (7)
O7	0.0265 (8)	0.0195 (7)	0.0249 (9)	−0.0051 (6)	−0.0064 (7)	0.0094 (6)
C17	0.0195 (10)	0.0175 (10)	0.0151 (11)	0.0030 (8)	−0.0030 (8)	0.0006 (8)
C18	0.0171 (10)	0.0188 (10)	0.0184 (11)	−0.0002 (8)	−0.0045 (8)	−0.0039 (8)
C19	0.0225 (11)	0.0150 (10)	0.0164 (11)	0.0022 (8)	−0.0019 (8)	0.0003 (8)
C20	0.0188 (10)	0.0180 (10)	0.0192 (11)	0.0044 (8)	−0.0044 (8)	0.0015 (8)
C21	0.0166 (10)	0.0180 (10)	0.0171 (11)	0.0007 (8)	−0.0028 (8)	−0.0012 (8)
C22	0.0186 (10)	0.0140 (9)	0.0154 (10)	0.0012 (8)	0.0000 (8)	−0.0013 (8)
C23	0.0206 (11)	0.0177 (10)	0.0172 (11)	0.0012 (8)	−0.0015 (8)	−0.0024 (8)
C24	0.0207 (11)	0.0213 (11)	0.0225 (12)	−0.0050 (9)	−0.0064 (9)	0.0031 (9)
C25	0.0231 (11)	0.0212 (11)	0.0187 (12)	−0.0005 (9)	−0.0040 (9)	0.0005 (9)
C26	0.0372 (14)	0.0209 (11)	0.0251 (13)	−0.0032 (10)	−0.0090 (10)	0.0097 (10)
O8	0.0225 (8)	0.0187 (7)	0.0248 (8)	−0.0061 (6)	−0.0082 (6)	0.0036 (6)
N3	0.0193 (9)	0.0176 (9)	0.0187 (10)	0.0017 (7)	−0.0017 (7)	0.0019 (7)
N4	0.0236 (10)	0.0167 (9)	0.0247 (11)	−0.0061 (8)	−0.0073 (8)	0.0069 (8)
C27	0.0220 (11)	0.0160 (10)	0.0182 (11)	0.0000 (8)	−0.0023 (8)	−0.0020 (8)
C28	0.0209 (11)	0.0188 (10)	0.0143 (10)	0.0026 (8)	−0.0009 (8)	0.0013 (8)
C29	0.0150 (10)	0.0152 (10)	0.0179 (11)	0.0020 (8)	−0.0010 (8)	0.0010 (8)
C30	0.0193 (10)	0.0176 (10)	0.0164 (11)	0.0034 (8)	−0.0048 (8)	−0.0026 (8)
C31	0.0210 (11)	0.0205 (10)	0.0155 (11)	0.0039 (9)	−0.0014 (8)	0.0027 (8)
C32	0.0205 (11)	0.0133 (10)	0.0182 (11)	0.0000 (8)	0.0005 (9)	0.0012 (8)
O4	0.0285 (9)	0.0220 (8)	0.0218 (8)	−0.0096 (7)	−0.0089 (7)	0.0036 (6)
N1	0.0198 (9)	0.0154 (8)	0.0186 (9)	0.0007 (7)	0.0001 (7)	0.0022 (7)
N2	0.0240 (10)	0.0187 (10)	0.0234 (11)	−0.0040 (8)	−0.0059 (8)	0.0067 (8)
C11	0.0159 (10)	0.0175 (10)	0.0179 (11)	−0.0007 (8)	−0.0029 (8)	−0.0005 (8)
C12	0.0171 (10)	0.0177 (10)	0.0174 (11)	0.0032 (8)	−0.0023 (8)	0.0013 (8)
C13	0.0219 (11)	0.0153 (10)	0.0129 (10)	0.0021 (8)	0.0021 (8)	−0.0003 (8)
C14	0.0162 (10)	0.0205 (10)	0.0165 (11)	0.0001 (8)	−0.0020 (8)	−0.0022 (8)
C15	0.0200 (11)	0.0208 (10)	0.0172 (11)	0.0034 (8)	−0.0031 (8)	0.0013 (8)
C16	0.0176 (10)	0.0154 (10)	0.0174 (11)	−0.0005 (8)	−0.0002 (8)	−0.0004 (8)

Geometric parameters (Å, º)

O1—C9	1.328 (2)	C22—C23	1.466 (3)
O1—H1	1.00 (2)	C23—H23	0.9500
O2—C9	1.226 (2)	C23—C24	1.331 (3)
O3—C3	1.370 (2)	C24—H24	0.9500
O3—C10	1.432 (2)	C24—C25	1.471 (3)
C1—H1A	0.9500	C26—H26A	0.9800
C1—C2	1.380 (3)	C26—H26B	0.9800
C1—C6	1.402 (3)	C26—H26C	0.9800
C2—H2	0.9500	O8—C32	1.239 (2)
C2—C3	1.393 (3)	N3—C27	1.342 (3)
C3—C4	1.389 (3)	N3—C31	1.340 (2)
C4—H4	0.9500	N4—C32	1.330 (3)
C4—C5	1.395 (3)	N4—H4A	0.96 (3)
C5—H5	0.9500	N4—H4B	0.92 (3)
C5—C6	1.392 (3)	C27—H27	0.9500
C6—C7	1.464 (3)	C27—C28	1.387 (3)
C7—H7	0.9500	C28—H28	0.9500
C7—C8	1.331 (3)	C28—C29	1.388 (3)
C8—H8	0.9500	C29—C30	1.392 (3)
C8—C9	1.469 (3)	C29—C32	1.506 (3)
C10—H10A	0.9800	C30—H30	0.9500
C10—H10B	0.9800	C30—C31	1.384 (3)
C10—H10C	0.9800	C31—H31	0.9500
O5—C25	1.324 (2)	O4—C16	1.232 (2)
O5—H5A	1.00 (2)	N1—C11	1.335 (2)
O6—C25	1.222 (2)	N1—C15	1.339 (3)
O7—C19	1.367 (2)	N2—C16	1.329 (3)
O7—C26	1.435 (2)	N2—H2A	0.96 (3)
C17—H17	0.9500	N2—H2B	0.90 (3)
C17—C18	1.377 (3)	C11—H11	0.9500
C17—C22	1.404 (3)	C11—C12	1.383 (3)
C18—H18	0.9500	C12—H12	0.9500
C18—C19	1.399 (3)	C12—C13	1.389 (3)
C19—C20	1.386 (3)	C13—C14	1.387 (3)
C20—H20	0.9500	C13—C16	1.520 (3)
C20—C21	1.389 (3)	C14—H14	0.9500
C21—H21	0.9500	C14—C15	1.387 (3)
C21—C22	1.392 (3)	C15—H15	0.9500
C9—O1—H1	108.5 (17)	C24—C23—H23	116.7
C3—O3—C10	116.99 (15)	C23—C24—H24	118.3
C2—C1—H1A	119.8	C23—C24—C25	123.4 (2)
C2—C1—C6	120.37 (19)	C25—C24—H24	118.3
C6—C1—H1A	119.8	O5—C25—C24	115.28 (18)
C1—C2—H2	119.7	O6—C25—O5	121.98 (19)
C1—C2—C3	120.54 (18)	O6—C25—C24	122.70 (19)
C3—C2—H2	119.7	O7—C26—H26A	109.5
O3—C3—C2	115.76 (17)	O7—C26—H26B	109.5
O3—C3—C4	123.86 (18)	O7—C26—H26C	109.5
C4—C3—C2	120.37 (17)	H26A—C26—H26B	109.5
C3—C4—H4	120.8	H26A—C26—H26C	109.5
C3—C4—C5	118.40 (18)	H26B—C26—H26C	109.5
C5—C4—H4	120.8	C31—N3—C27	118.00 (17)
C4—C5—H5	118.9	C32—N4—H4A	121.3 (17)
C6—C5—C4	122.15 (18)	C32—N4—H4B	121.6 (17)
C6—C5—H5	118.9	H4A—N4—H4B	117 (2)
C1—C6—C7	123.11 (18)	N3—C27—H27	118.7
C5—C6—C1	118.15 (18)	N3—C27—C28	122.59 (18)
C5—C6—C7	118.70 (17)	C28—C27—H27	118.7
C6—C7—H7	116.4	C27—C28—H28	120.4
C8—C7—C6	127.25 (19)	C27—C28—C29	119.23 (19)
C8—C7—H7	116.4	C29—C28—H28	120.4
C7—C8—H8	118.3	C28—C29—C30	118.23 (18)
C7—C8—C9	123.37 (19)	C28—C29—C32	123.49 (18)
C9—C8—H8	118.3	C30—C29—C32	118.25 (17)
O1—C9—C8	114.86 (18)	C29—C30—H30	120.5
O2—C9—O1	122.39 (18)	C31—C30—C29	118.93 (18)
O2—C9—C8	122.75 (19)	C31—C30—H30	120.5
O3—C10—H10A	109.5	N3—C31—C30	123.00 (19)
O3—C10—H10B	109.5	N3—C31—H31	118.5
O3—C10—H10C	109.5	C30—C31—H31	118.5
H10A—C10—H10B	109.5	O8—C32—N4	124.07 (18)
H10A—C10—H10C	109.5	O8—C32—C29	119.08 (18)
H10B—C10—H10C	109.5	N4—C32—C29	116.84 (18)
C25—O5—H5A	108.5 (16)	C11—N1—C15	117.42 (17)
C19—O7—C26	117.22 (16)	C16—N2—H2A	118.2 (16)
C18—C17—H17	119.6	C16—N2—H2B	121.7 (16)
C18—C17—C22	120.70 (19)	H2A—N2—H2B	120 (2)
C22—C17—H17	119.6	N1—C11—H11	118.4
C17—C18—H18	119.9	N1—C11—C12	123.29 (19)
C17—C18—C19	120.16 (19)	C12—C11—H11	118.4
C19—C18—H18	119.9	C11—C12—H12	120.5
O7—C19—C18	115.40 (18)	C11—C12—C13	118.94 (18)
O7—C19—C20	124.57 (18)	C13—C12—H12	120.5
C20—C19—C18	120.03 (18)	C12—C13—C16	123.66 (18)
C19—C20—H20	120.4	C14—C13—C12	118.39 (18)
C19—C20—C21	119.26 (19)	C14—C13—C16	117.93 (18)
C21—C20—H20	120.4	C13—C14—H14	120.7
C20—C21—H21	119.2	C13—C14—C15	118.58 (19)
C20—C21—C22	121.63 (19)	C15—C14—H14	120.7
C22—C21—H21	119.2	N1—C15—C14	123.37 (19)
C17—C22—C23	123.42 (18)	N1—C15—H15	118.3
C21—C22—C17	118.20 (18)	C14—C15—H15	118.3
C21—C22—C23	118.33 (18)	O4—C16—N2	124.14 (19)
C22—C23—H23	116.7	O4—C16—C13	119.16 (18)
C24—C23—C22	126.7 (2)	N2—C16—C13	116.69 (18)
O3—C3—C4—C5	179.70 (17)	C22—C23—C24—C25	−176.11 (18)
C1—C2—C3—O3	−179.18 (17)	C23—C24—C25—O5	9.1 (3)
C1—C2—C3—C4	−0.2 (3)	C23—C24—C25—O6	−172.7 (2)
C1—C6—C7—C8	−7.1 (3)	C26—O7—C19—C18	176.63 (17)
C2—C1—C6—C5	1.2 (3)	C26—O7—C19—C20	−3.2 (3)
C2—C1—C6—C7	−176.35 (18)	N3—C27—C28—C29	−0.6 (3)
C2—C3—C4—C5	0.9 (3)	C27—N3—C31—C30	0.4 (3)
C3—C4—C5—C6	−0.4 (3)	C27—C28—C29—C30	−0.7 (3)
C4—C5—C6—C1	−0.6 (3)	C27—C28—C29—C32	−178.37 (18)
C4—C5—C6—C7	177.08 (17)	C28—C29—C30—C31	1.7 (3)
C5—C6—C7—C8	175.3 (2)	C28—C29—C32—O8	151.55 (19)
C6—C1—C2—C3	−0.8 (3)	C28—C29—C32—N4	−27.6 (3)
C6—C7—C8—C9	178.34 (18)	C29—C30—C31—N3	−1.6 (3)
C7—C8—C9—O1	−11.3 (3)	C30—C29—C32—O8	−26.2 (3)
C7—C8—C9—O2	169.4 (2)	C30—C29—C32—N4	154.74 (18)
C10—O3—C3—C2	−177.94 (17)	C31—N3—C27—C28	0.7 (3)
C10—O3—C3—C4	3.2 (3)	C32—C29—C30—C31	179.48 (17)
O7—C19—C20—C21	179.22 (17)	N1—C11—C12—C13	0.6 (3)
C17—C18—C19—O7	−179.32 (16)	C11—N1—C15—C14	0.4 (3)
C17—C18—C19—C20	0.5 (3)	C11—C12—C13—C14	0.7 (3)
C17—C22—C23—C24	1.9 (3)	C11—C12—C13—C16	178.79 (17)
C18—C17—C22—C21	−1.5 (3)	C12—C13—C14—C15	−1.4 (3)
C18—C17—C22—C23	175.96 (17)	C12—C13—C16—O4	−160.72 (19)
C18—C19—C20—C21	−0.6 (3)	C12—C13—C16—N2	18.7 (3)
C19—C20—C21—C22	−0.4 (3)	C13—C14—C15—N1	0.8 (3)
C20—C21—C22—C17	1.4 (3)	C14—C13—C16—O4	17.4 (3)
C20—C21—C22—C23	−176.18 (17)	C14—C13—C16—N2	−163.27 (18)
C21—C22—C23—C24	179.34 (19)	C15—N1—C11—C12	−1.1 (3)
C22—C17—C18—C19	0.5 (3)	C16—C13—C14—C15	−179.53 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O8^i	0.96 (3)	1.93 (3)	2.878 (2)	175 (2)
N2—H2A···O4^ii	0.96 (3)	1.96 (3)	2.917 (2)	173 (2)
O1—H1···N3	1.00 (2)	1.66 (2)	2.665 (2)	175 (3)
O5—H5A···N1	1.00 (2)	1.68 (2)	2.675 (2)	173 (2)
N4—H4B···O2^iii	0.92 (3)	2.04 (3)	2.953 (2)	171 (2)
N2—H2B···O6^iv	0.90 (3)	2.04 (3)	2.934 (2)	173 (2)

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

(4B)

Crystal data

C11H12O4·C6H6N2O	F(000) = 696
Mr = 330.33	Dx = 1.371 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.0200 (8) Å	Cell parameters from 1157 reflections
b = 9.8795 (5) Å	θ = 2.5–27.7°
c = 11.6434 (6) Å	µ = 0.10 mm^−1
β = 96.975 (4)°	T = 100 K
V = 1600.80 (15) Å^3	Plate, colourless
Z = 4	0.37 × 0.27 × 0.16 mm

Data collection

Bruker Apex II kappa CCD area detector diffractometer	3896 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.085
φ and ω scans	θmax = 28.1°, θmin = 1.5°
Absorption correction: multi-scan SADABS2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0619 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.9013. The λ/2 correction factor is 0.00150.	h = −18→13
Tmin = 0.672, Tmax = 0.746	k = −13→12
14321 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0556P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3896 reflections	Δρmax = 0.25 e Å^−3
231 parameters	Δρmin = −0.32 e Å^−3
1 restraint

Special details

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

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

	x	y	z	Uiso*/Ueq
O1	0.70928 (12)	0.44610 (14)	0.25409 (14)	0.0243 (4)
H1	0.684 (2)	0.452 (3)	0.1701 (7)	0.073 (11)*
O2	0.64521 (11)	0.65394 (15)	0.24844 (14)	0.0265 (4)
O3	0.88680 (11)	0.47245 (14)	0.97075 (13)	0.0237 (4)
O4	0.91711 (11)	0.26152 (14)	0.84940 (14)	0.0267 (4)
C1	0.78704 (15)	0.5964 (2)	0.6831 (2)	0.0206 (5)
H1A	0.7563	0.6742	0.6477	0.025*
C2	0.81427 (15)	0.5959 (2)	0.8012 (2)	0.0221 (5)
H2	0.8029	0.6733	0.8459	0.027*
C3	0.85798 (15)	0.4833 (2)	0.85452 (19)	0.0209 (5)
C4	0.87445 (15)	0.3687 (2)	0.7877 (2)	0.0215 (5)
C5	0.84866 (15)	0.3707 (2)	0.6697 (2)	0.0216 (5)
H5	0.8614	0.2940	0.6248	0.026*
C6	0.80366 (15)	0.4851 (2)	0.61475 (19)	0.0199 (5)
C7	0.77319 (15)	0.4805 (2)	0.4900 (2)	0.0213 (5)
H7	0.7956	0.4063	0.4488	0.026*
C8	0.71704 (16)	0.5704 (2)	0.4282 (2)	0.0218 (5)
H8	0.6945	0.6454	0.4682	0.026*
C9	0.68771 (16)	0.5613 (2)	0.3027 (2)	0.0203 (5)
C10	0.88237 (17)	0.5938 (2)	1.0373 (2)	0.0272 (6)
H10A	0.9172	0.6663	1.0029	0.041*
H10B	0.9117	0.5776	1.1169	0.041*
H10C	0.8151	0.6206	1.0378	0.041*
C11	0.94348 (18)	0.1483 (2)	0.7837 (2)	0.0310 (6)
H11A	0.9848	0.1789	0.7267	0.046*
H11B	0.8855	0.1062	0.7436	0.046*
H11C	0.9783	0.0821	0.8357	0.046*
O5	0.53991 (11)	0.37633 (14)	−0.38715 (14)	0.0246 (4)
N1	0.64733 (12)	0.45071 (17)	0.03376 (16)	0.0194 (4)
N2	0.53537 (15)	0.60408 (19)	−0.37305 (18)	0.0226 (5)
H2A	0.5516 (17)	0.675 (2)	−0.332 (2)	0.029 (7)*
H2B	0.5135 (16)	0.610 (2)	−0.452 (2)	0.024 (6)*
C12	0.65593 (16)	0.3474 (2)	−0.0384 (2)	0.0222 (5)
H12	0.6838	0.2655	−0.0074	0.027*
C13	0.62619 (15)	0.3538 (2)	−0.15608 (19)	0.0200 (5)
H13	0.6343	0.2785	−0.2047	0.024*
C14	0.58421 (14)	0.4729 (2)	−0.20158 (19)	0.0176 (5)
C15	0.57285 (15)	0.5794 (2)	−0.12662 (19)	0.0201 (5)
H15	0.5431	0.6613	−0.1546	0.024*
C16	0.60561 (15)	0.5639 (2)	−0.01080 (19)	0.0203 (5)
H16	0.5981	0.6375	0.0399	0.024*
C17	0.55146 (15)	0.4807 (2)	−0.3288 (2)	0.0189 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0360 (10)	0.0183 (8)	0.0174 (9)	0.0032 (7)	−0.0011 (8)	−0.0026 (7)
O2	0.0344 (10)	0.0221 (8)	0.0223 (9)	0.0058 (7)	0.0002 (8)	0.0018 (7)
O3	0.0280 (9)	0.0214 (8)	0.0205 (9)	−0.0001 (6)	−0.0013 (7)	−0.0001 (7)
O4	0.0309 (9)	0.0186 (8)	0.0282 (10)	0.0051 (6)	−0.0059 (8)	0.0001 (7)
C1	0.0193 (11)	0.0205 (11)	0.0219 (13)	0.0004 (9)	0.0027 (10)	0.0014 (9)
C2	0.0190 (12)	0.0219 (11)	0.0251 (14)	−0.0015 (9)	0.0020 (10)	−0.0011 (10)
C3	0.0180 (11)	0.0256 (12)	0.0181 (12)	−0.0035 (9)	−0.0017 (9)	−0.0009 (10)
C4	0.0188 (12)	0.0201 (11)	0.0248 (13)	−0.0013 (9)	−0.0003 (10)	0.0015 (10)
C5	0.0189 (12)	0.0206 (11)	0.0251 (13)	−0.0011 (9)	0.0012 (10)	−0.0036 (10)
C6	0.0191 (11)	0.0218 (11)	0.0183 (12)	−0.0030 (9)	0.0008 (9)	−0.0005 (9)
C7	0.0211 (12)	0.0195 (11)	0.0233 (13)	−0.0040 (9)	0.0023 (10)	−0.0020 (10)
C8	0.0255 (12)	0.0216 (11)	0.0183 (12)	−0.0015 (9)	0.0030 (10)	−0.0024 (10)
C9	0.0232 (12)	0.0194 (11)	0.0186 (12)	−0.0031 (9)	0.0040 (10)	0.0002 (9)
C10	0.0326 (14)	0.0274 (12)	0.0205 (13)	−0.0026 (10)	−0.0006 (11)	−0.0046 (10)
C11	0.0307 (14)	0.0241 (12)	0.0372 (16)	0.0078 (10)	0.0004 (12)	−0.0036 (11)
O5	0.0334 (10)	0.0190 (8)	0.0208 (9)	−0.0029 (6)	0.0012 (7)	−0.0027 (7)
N1	0.0212 (10)	0.0186 (9)	0.0183 (10)	−0.0006 (7)	0.0015 (8)	0.0000 (8)
N2	0.0333 (12)	0.0198 (10)	0.0135 (11)	−0.0034 (8)	−0.0019 (9)	−0.0004 (9)
C12	0.0243 (12)	0.0194 (11)	0.0219 (13)	0.0028 (9)	−0.0008 (10)	0.0032 (10)
C13	0.0221 (12)	0.0165 (10)	0.0214 (13)	−0.0016 (9)	0.0022 (10)	−0.0019 (9)
C14	0.0148 (11)	0.0181 (11)	0.0203 (12)	−0.0046 (8)	0.0031 (9)	−0.0020 (9)
C15	0.0230 (12)	0.0166 (11)	0.0209 (13)	0.0014 (8)	0.0037 (10)	0.0033 (9)
C16	0.0232 (12)	0.0189 (11)	0.0190 (12)	0.0001 (9)	0.0032 (10)	−0.0026 (9)
C17	0.0198 (11)	0.0184 (11)	0.0187 (12)	−0.0023 (8)	0.0025 (9)	−0.0001 (9)

Geometric parameters (Å, º)

O1—H1	1.0000 (10)	C10—H10A	0.9800
O1—C9	1.322 (3)	C10—H10B	0.9800
O2—C9	1.225 (2)	C10—H10C	0.9800
O3—C3	1.369 (3)	C11—H11A	0.9800
O3—C10	1.434 (2)	C11—H11B	0.9800
O4—C4	1.375 (2)	C11—H11C	0.9800
O4—C11	1.429 (3)	O5—C17	1.234 (2)
C1—H1A	0.9500	N1—C12	1.337 (3)
C1—C2	1.382 (3)	N1—C16	1.337 (3)
C1—C6	1.393 (3)	N2—H2A	0.87 (2)
C2—H2	0.9500	N2—H2B	0.93 (2)
C2—C3	1.381 (3)	N2—C17	1.332 (3)
C3—C4	1.409 (3)	C12—H12	0.9500
C4—C5	1.378 (3)	C12—C13	1.384 (3)
C5—H5	0.9500	C13—H13	0.9500
C5—C6	1.410 (3)	C13—C14	1.391 (3)
C6—C7	1.464 (3)	C14—C15	1.388 (3)
C7—H7	0.9500	C14—C17	1.499 (3)
C7—C8	1.337 (3)	C15—H15	0.9500
C8—H8	0.9500	C15—C16	1.379 (3)
C8—C9	1.472 (3)	C16—H16	0.9500
C9—O1—H1	107.3 (17)	O3—C10—H10C	109.5
C3—O3—C10	116.27 (16)	H10A—C10—H10B	109.5
C4—O4—C11	116.57 (18)	H10A—C10—H10C	109.5
C2—C1—H1A	119.3	H10B—C10—H10C	109.5
C2—C1—C6	121.4 (2)	O4—C11—H11A	109.5
C6—C1—H1A	119.3	O4—C11—H11B	109.5
C1—C2—H2	119.9	O4—C11—H11C	109.5
C3—C2—C1	120.3 (2)	H11A—C11—H11B	109.5
C3—C2—H2	119.9	H11A—C11—H11C	109.5
O3—C3—C2	124.7 (2)	H11B—C11—H11C	109.5
O3—C3—C4	115.78 (19)	C12—N1—C16	117.60 (19)
C2—C3—C4	119.5 (2)	H2A—N2—H2B	121 (2)
O4—C4—C3	114.8 (2)	C17—N2—H2A	120.7 (16)
O4—C4—C5	125.2 (2)	C17—N2—H2B	117.4 (13)
C5—C4—C3	119.9 (2)	N1—C12—H12	118.4
C4—C5—H5	119.6	N1—C12—C13	123.21 (19)
C4—C5—C6	120.9 (2)	C13—C12—H12	118.4
C6—C5—H5	119.6	C12—C13—H13	120.7
C1—C6—C5	118.1 (2)	C12—C13—C14	118.6 (2)
C1—C6—C7	122.8 (2)	C14—C13—H13	120.7
C5—C6—C7	119.1 (2)	C13—C14—C17	118.97 (19)
C6—C7—H7	116.7	C15—C14—C13	118.5 (2)
C8—C7—C6	126.5 (2)	C15—C14—C17	122.55 (19)
C8—C7—H7	116.7	C14—C15—H15	120.6
C7—C8—H8	117.7	C16—C15—C14	118.7 (2)
C7—C8—C9	124.7 (2)	C16—C15—H15	120.6
C9—C8—H8	117.7	N1—C16—C15	123.4 (2)
O1—C9—C8	115.27 (18)	N1—C16—H16	118.3
O2—C9—O1	123.0 (2)	C15—C16—H16	118.3
O2—C9—C8	121.7 (2)	O5—C17—N2	123.2 (2)
O3—C10—H10A	109.5	O5—C17—C14	120.34 (19)
O3—C10—H10B	109.5	N2—C17—C14	116.50 (19)
O3—C3—C4—O4	0.2 (3)	C7—C8—C9—O2	−171.7 (2)
O3—C3—C4—C5	−179.4 (2)	C10—O3—C3—C2	−8.8 (3)
O4—C4—C5—C6	178.9 (2)	C10—O3—C3—C4	171.92 (19)
C1—C2—C3—O3	−179.4 (2)	C11—O4—C4—C3	−174.17 (19)
C1—C2—C3—C4	−0.1 (3)	C11—O4—C4—C5	5.4 (3)
C1—C6—C7—C8	−8.7 (4)	N1—C12—C13—C14	−0.8 (3)
C2—C1—C6—C5	0.5 (3)	C12—N1—C16—C15	−1.0 (3)
C2—C1—C6—C7	178.1 (2)	C12—C13—C14—C15	−0.9 (3)
C2—C3—C4—O4	−179.13 (19)	C12—C13—C14—C17	−179.78 (19)
C2—C3—C4—C5	1.3 (3)	C13—C14—C15—C16	1.5 (3)
C3—C4—C5—C6	−1.5 (3)	C13—C14—C17—O5	17.5 (3)
C4—C5—C6—C1	0.7 (3)	C13—C14—C17—N2	−163.1 (2)
C4—C5—C6—C7	−177.0 (2)	C14—C15—C16—N1	−0.6 (3)
C5—C6—C7—C8	168.9 (2)	C15—C14—C17—O5	−161.4 (2)
C6—C1—C2—C3	−0.8 (3)	C15—C14—C17—N2	18.0 (3)
C6—C7—C8—C9	−179.6 (2)	C16—N1—C12—C13	1.7 (3)
C7—C8—C9—O1	9.3 (3)	C17—C14—C15—C16	−179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	1.00 (1)	1.61 (1)	2.607 (2)	176 (3)
N2—H2B···O5^i	0.93 (2)	1.94 (3)	2.869 (3)	176 (2)

Symmetry code: (i) −x+1, −y+1, −z−1.