N-(3,4-Dimethyl-phen-yl)maleamic acid.

The title compound, C(12)H(13)NO(3), crystallizes with four independent mol-ecules in the asymmetric unit. The N-H bond and the C=O bond in the amide segment are anti to each other. The C=C double bond is cis configured and an intra-molecular O-H⋯O hydrogen bond is formed in each molecule. The mean planes through the aromatic ring and the amide group -NHCO- are inclined at angles of 17.4 (3), 20.8 (2), 16.2 (2) and 11.2 (3)° in the four mol-ecules. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into ribbons along the b axis.

Related literature

For our study on the effect of ring and side-chain substitutions on the crystal structures of biologically important amides, see: Gowda, Foro, Saraswathi & Fuess (2009 ▶); Gowda, Foro, Saraswathi, Terao & Fuess (2009 ▶); Gowda, Tokarčík et al. (2009 ▶); Prasad et al. (2002 ▶). For modes of inter­linking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶). For a related structure, see: Lo & Ng (2009 ▶).

Experimental

Crystal data

C12H13NO3

M = 219.23

Monoclinic,

a = 11.9003 (2) Å

b = 12.9991 (2) Å

c = 15.2641 (3) Å

β = 110.207 (2)°

V = 2215.92 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.48 × 0.32 × 0.31 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2009 ▶) T min = 0.958, T max = 0.965

67608 measured reflections

5279 independent reflections

4100 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.134

S = 1.03

5279 reflections

577 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶), PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043682/bt5110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043682/bt5110Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H13NO3	F(000) = 928
Mr = 219.23	Dx = 1.314 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 31828 reflections
a = 11.9003 (2) Å	θ = 1.9–27.8°
b = 12.9991 (2) Å	µ = 0.10 mm−1
c = 15.2641 (3) Å	T = 295 K
β = 110.207 (2)°	Truncated square pyramid, colourless
V = 2215.92 (7) Å3	0.48 × 0.32 × 0.31 mm
Z = 8

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	5279 independent reflections
graphite	4100 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.028
ω scans	θmax = 27.9°, θmin = 2.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −15→15
Tmin = 0.958, Tmax = 0.965	k = −17→17
67608 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0958P)2 + 0.0272P] where P = (Fo2 + 2Fc2)/3
5279 reflections	(Δ/σ)max = 0.001
577 parameters	Δρmax = 0.29 e Å−3
10 restraints	Δρmin = −0.16 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.5468 (2)	0.4000 (2)	0.1080 (2)	0.0430 (6)
C2	0.6117 (3)	0.4743 (2)	0.0804 (2)	0.0450 (6)
H2	0.5758	0.5365	0.056	0.054*
C3	0.7309 (3)	0.4559 (2)	0.0893 (2)	0.0462 (7)
C4	0.7851 (3)	0.3631 (2)	0.1243 (2)	0.0474 (7)
C5	0.7189 (3)	0.2888 (2)	0.1513 (2)	0.0493 (7)
H5	0.7544	0.2264	0.1755	0.059*
C6	0.6006 (3)	0.3075 (2)	0.1423 (2)	0.0484 (7)
H6	0.5571	0.2569	0.1596	0.058*
C7	0.3634 (3)	0.4981 (2)	0.0983 (2)	0.0468 (6)
C8	0.2429 (3)	0.4810 (3)	0.1042 (3)	0.0564 (8)
H8	0.2164	0.4132	0.0976	0.068*
C9	0.1684 (3)	0.5495 (2)	0.1176 (3)	0.0585 (8)
H9	0.0983	0.5213	0.1212	0.07*
C10	0.1759 (3)	0.6647 (2)	0.1281 (2)	0.0524 (7)
C11	0.7982 (3)	0.5385 (2)	0.0590 (3)	0.0589 (8)
H11A	0.8646	0.5613	0.1118	0.088*
H11B	0.7457	0.5955	0.0336	0.088*
H11C	0.8272	0.5115	0.0123	0.088*
C12	0.9124 (3)	0.3412 (3)	0.1342 (3)	0.0626 (9)
H12A	0.9338	0.2734	0.1594	0.094*	0.5
H12B	0.9639	0.3909	0.1754	0.094*	0.5
H12C	0.9211	0.3453	0.074	0.094*	0.5
H12D	0.9455	0.3996	0.1131	0.094*	0.5
H12E	0.9153	0.2822	0.0972	0.094*	0.5
H12F	0.9581	0.3278	0.1985	0.094*	0.5
N1	0.4259 (2)	0.41119 (17)	0.10310 (19)	0.0495 (6)
H1	0.3879	0.3549	0.1032	0.059*
O1	0.40148 (19)	0.58444 (16)	0.08902 (19)	0.0609 (6)
O2	0.2602 (2)	0.71471 (17)	0.1095 (2)	0.0745 (7)
H2A	0.3048	0.671	0.092	0.089*
O3	0.1018 (2)	0.70943 (18)	0.1511 (2)	0.0708 (7)
C21	−0.0264 (2)	0.63766 (18)	0.36357 (17)	0.0369 (5)
C22	−0.0921 (3)	0.7141 (2)	0.38831 (19)	0.0388 (6)
H22	−0.0562	0.7768	0.4112	0.047*
C23	−0.2114 (2)	0.69692 (19)	0.37893 (18)	0.0382 (6)
C24	−0.2663 (2)	0.6027 (2)	0.34333 (18)	0.0405 (6)
C25	−0.1979 (3)	0.5278 (2)	0.3203 (2)	0.0480 (7)
H25	−0.2328	0.4647	0.2978	0.058*
C26	−0.0802 (3)	0.5444 (2)	0.3298 (2)	0.0471 (7)
H26	−0.0366	0.4931	0.3135	0.056*
C27	0.1559 (3)	0.7351 (2)	0.3711 (2)	0.0429 (6)
C28	0.2785 (3)	0.7178 (2)	0.3698 (2)	0.0505 (7)
H28	0.3061	0.6503	0.3785	0.061*
C29	0.3543 (3)	0.7882 (2)	0.3577 (3)	0.0552 (8)
H29	0.4274	0.7609	0.3597	0.066*
C30	0.3450 (3)	0.8997 (2)	0.3418 (2)	0.0511 (7)
C31	−0.2811 (3)	0.7797 (2)	0.4058 (2)	0.0525 (7)
H31A	−0.2289	0.8363	0.4332	0.079*
H31B	−0.3142	0.7529	0.4503	0.079*
H31C	−0.3447	0.8029	0.3513	0.079*
C32	−0.3959 (3)	0.5826 (3)	0.3293 (2)	0.0548 (7)
H32A	−0.415	0.5124	0.3107	0.082*
H32B	−0.4455	0.6275	0.2816	0.082*
H32C	−0.41	0.5952	0.3866	0.082*
N2	0.09531 (19)	0.64905 (16)	0.37116 (16)	0.0417 (5)
H2N	0.1352	0.5928	0.3765	0.05*
O21	0.11403 (19)	0.82277 (15)	0.37276 (19)	0.0594 (6)
O22	0.2552 (2)	0.95070 (16)	0.3502 (2)	0.0701 (8)
H22A	0.2037	0.9074	0.3597	0.084*
O23	0.4227 (2)	0.94389 (17)	0.3212 (2)	0.0689 (7)
C41	0.6529 (2)	0.13584 (19)	0.35178 (18)	0.0367 (5)
C42	0.7424 (3)	0.2090 (2)	0.3831 (2)	0.0413 (6)
H42	0.7261	0.2714	0.406	0.05*
C43	0.8552 (2)	0.1909 (2)	0.38079 (19)	0.0400 (5)
C44	0.8820 (2)	0.0970 (2)	0.3492 (2)	0.0408 (6)
C45	0.7941 (3)	0.0228 (2)	0.3204 (2)	0.0488 (7)
H45	0.8121	−0.0407	0.3004	0.059*
C46	0.6794 (2)	0.04100 (19)	0.3205 (2)	0.0441 (6)
H46	0.6206	−0.0094	0.3	0.053*
C47	0.4769 (2)	0.23407 (19)	0.3576 (2)	0.0428 (6)
C48	0.3514 (3)	0.2177 (2)	0.3524 (3)	0.0518 (7)
H48	0.3262	0.1496	0.3481	0.062*
C49	0.2708 (3)	0.2873 (2)	0.3530 (3)	0.0578 (8)
H49	0.1977	0.2596	0.3505	0.069*
C50	0.2750 (3)	0.4020 (2)	0.3570 (2)	0.0538 (7)
C51	0.9488 (3)	0.2750 (2)	0.4126 (3)	0.0619 (9)
H51A	0.9188	0.3299	0.4405	0.093*
H51B	0.9664	0.3009	0.3599	0.093*
H51C	1.0204	0.2475	0.4576	0.093*
C52	1.0043 (3)	0.0740 (3)	0.3436 (3)	0.0600 (8)
H52A	1.0097	0.0021	0.3313	0.09*
H52B	1.0652	0.0917	0.4017	0.09*
H52C	1.0154	0.1137	0.2941	0.09*
N3	0.53418 (19)	0.14672 (16)	0.35181 (16)	0.0420 (5)
H3N	0.4942	0.0907	0.3476	0.05*
O41	0.52359 (19)	0.31979 (15)	0.3658 (2)	0.0668 (7)
O42	0.3700 (2)	0.45152 (16)	0.3612 (2)	0.0663 (7)
H42A	0.4274	0.4076	0.3639	0.08*
O43	0.1861 (2)	0.44801 (18)	0.3567 (2)	0.0835 (9)
C61	−0.1341 (3)	0.8982 (2)	0.11567 (19)	0.0422 (6)
C62	−0.2221 (3)	0.9730 (2)	0.0861 (2)	0.0452 (6)
H62	−0.2043	1.0366	0.0661	0.054*
C63	−0.3375 (3)	0.9533 (2)	0.0862 (2)	0.0468 (6)
C64	−0.3650 (3)	0.8579 (2)	0.1163 (2)	0.0489 (7)
C65	−0.2730 (3)	0.7836 (2)	0.1469 (2)	0.0507 (7)
H65	−0.2894	0.7198	0.1673	0.061*
C66	−0.1596 (3)	0.8041 (2)	0.1469 (2)	0.0502 (7)
H66	−0.0998	0.7546	0.1679	0.06*
C67	0.0405 (3)	0.9968 (2)	0.1050 (2)	0.0466 (7)
C68	0.1659 (3)	0.9812 (2)	0.1108 (2)	0.0523 (8)
H68	0.1915	0.9132	0.115	0.063*
C69	0.2463 (3)	1.0512 (2)	0.1108 (3)	0.0615 (8)
H69	0.3196	1.0235	0.1137	0.074*
C70	0.2430 (3)	1.1660 (2)	0.1070 (3)	0.0554 (8)
C71	−0.4309 (3)	1.0354 (3)	0.0559 (3)	0.0679 (9)
H71A	−0.4987	1.0102	0.0055	0.102*
H71B	−0.3985	1.0946	0.0354	0.102*
H71C	−0.4555	1.0542	0.1074	0.102*
C72	−0.4875 (3)	0.8336 (3)	0.1182 (3)	0.0653 (9)
H72A	−0.4884	0.7648	0.1407	0.098*	0.5
H72B	−0.5452	0.8394	0.0562	0.098*	0.5
H72C	−0.5074	0.8812	0.1587	0.098*	0.5
H72D	−0.5389	0.8921	0.0964	0.098*	0.5
H72E	−0.4821	0.8175	0.1809	0.098*	0.5
H72F	−0.5199	0.7757	0.0784	0.098*	0.5
N4	−0.0147 (2)	0.91139 (17)	0.11665 (17)	0.0450 (5)
H4N	0.0278	0.8563	0.1261	0.054*
O61	−0.0095 (2)	1.08224 (16)	0.0903 (2)	0.0649 (6)
O62	0.1442 (2)	1.21427 (16)	0.09843 (19)	0.0637 (6)
H62A	0.0882	1.1694	0.0969	0.076*
O63	0.3342 (2)	1.21084 (19)	0.1144 (3)	0.0878 (9)

	U11	U22	U33	U12	U13	U23
C1	0.0381 (14)	0.0391 (13)	0.0533 (15)	−0.0002 (11)	0.0177 (12)	−0.0032 (11)
C2	0.0439 (16)	0.0392 (14)	0.0527 (16)	−0.0027 (12)	0.0178 (13)	0.0025 (12)
C3	0.0528 (18)	0.0398 (14)	0.0507 (17)	−0.0023 (12)	0.0238 (14)	−0.0044 (11)
C4	0.0418 (16)	0.0443 (15)	0.0589 (17)	0.0038 (12)	0.0209 (14)	−0.0069 (12)
C5	0.0468 (16)	0.0394 (14)	0.0616 (18)	0.0040 (12)	0.0187 (15)	0.0006 (13)
C6	0.0461 (17)	0.0347 (13)	0.0676 (19)	0.0014 (12)	0.0240 (14)	0.0011 (12)
C7	0.0356 (14)	0.0372 (14)	0.0689 (18)	0.0015 (11)	0.0196 (13)	0.0007 (12)
C8	0.0403 (16)	0.0445 (16)	0.085 (2)	−0.0039 (13)	0.0220 (16)	−0.0029 (15)
C9	0.0415 (16)	0.0452 (16)	0.093 (2)	−0.0009 (13)	0.0282 (16)	0.0067 (15)
C10	0.0465 (16)	0.0411 (15)	0.0701 (19)	0.0039 (13)	0.0209 (14)	0.0039 (13)
C11	0.0536 (18)	0.0518 (17)	0.082 (2)	−0.0080 (14)	0.0370 (17)	−0.0011 (15)
C12	0.0453 (18)	0.065 (2)	0.080 (2)	0.0038 (15)	0.0249 (17)	−0.0128 (16)
N1	0.0429 (13)	0.0365 (12)	0.0731 (16)	−0.0020 (10)	0.0253 (12)	−0.0008 (11)
O1	0.0457 (11)	0.0383 (10)	0.1082 (18)	−0.0021 (9)	0.0386 (12)	−0.0003 (11)
O2	0.0640 (16)	0.0378 (12)	0.137 (2)	0.0040 (10)	0.0545 (16)	0.0031 (12)
O3	0.0603 (14)	0.0574 (14)	0.1057 (18)	0.0152 (11)	0.0428 (14)	0.0056 (12)
C21	0.0358 (13)	0.0307 (12)	0.0480 (15)	0.0021 (10)	0.0194 (11)	−0.0004 (10)
C22	0.0402 (14)	0.0299 (12)	0.0512 (15)	−0.0014 (10)	0.0220 (12)	−0.0030 (10)
C23	0.0389 (14)	0.0327 (12)	0.0469 (15)	0.0058 (10)	0.0197 (12)	0.0027 (10)
C24	0.0396 (14)	0.0398 (14)	0.0453 (14)	−0.0043 (11)	0.0187 (12)	0.0004 (11)
C25	0.0519 (18)	0.0355 (13)	0.0623 (19)	−0.0108 (12)	0.0270 (15)	−0.0101 (12)
C26	0.0515 (17)	0.0333 (13)	0.0658 (18)	−0.0012 (11)	0.0323 (14)	−0.0067 (11)
C27	0.0430 (15)	0.0326 (13)	0.0592 (17)	0.0004 (11)	0.0256 (13)	−0.0017 (11)
C28	0.0410 (15)	0.0294 (12)	0.087 (2)	0.0030 (11)	0.0293 (15)	−0.0044 (13)
C29	0.0320 (14)	0.0447 (16)	0.095 (2)	−0.0003 (12)	0.0291 (15)	−0.0055 (15)
C30	0.0359 (15)	0.0408 (15)	0.078 (2)	−0.0089 (12)	0.0219 (14)	−0.0089 (13)
C31	0.0512 (17)	0.0390 (14)	0.076 (2)	0.0089 (12)	0.0335 (16)	−0.0027 (13)
C32	0.0438 (16)	0.0537 (17)	0.0700 (19)	−0.0067 (14)	0.0238 (15)	−0.0015 (14)
N2	0.0338 (11)	0.0292 (10)	0.0679 (15)	0.0024 (8)	0.0249 (11)	−0.0017 (9)
O21	0.0489 (11)	0.0289 (9)	0.1141 (18)	0.0038 (8)	0.0455 (12)	−0.0007 (10)
O22	0.0547 (15)	0.0347 (11)	0.137 (2)	−0.0010 (9)	0.0542 (16)	0.0025 (12)
O23	0.0545 (13)	0.0493 (12)	0.1149 (19)	−0.0133 (11)	0.0444 (13)	−0.0027 (12)
C41	0.0361 (14)	0.0295 (11)	0.0482 (15)	0.0044 (10)	0.0190 (11)	0.0018 (10)
C42	0.0459 (15)	0.0303 (12)	0.0509 (15)	0.0042 (10)	0.0207 (12)	−0.0038 (10)
C43	0.0354 (13)	0.0326 (12)	0.0511 (15)	0.0018 (10)	0.0140 (12)	−0.0004 (11)
C44	0.0352 (14)	0.0378 (13)	0.0527 (15)	0.0093 (10)	0.0191 (12)	0.0015 (11)
C45	0.0478 (16)	0.0313 (12)	0.072 (2)	0.0049 (11)	0.0273 (15)	−0.0074 (12)
C46	0.0387 (14)	0.0286 (12)	0.0659 (18)	0.0019 (10)	0.0191 (13)	−0.0042 (11)
C47	0.0380 (14)	0.0272 (12)	0.0672 (18)	0.0044 (10)	0.0231 (13)	0.0005 (11)
C48	0.0461 (16)	0.0309 (13)	0.088 (2)	−0.0034 (12)	0.0348 (16)	−0.0037 (13)
C49	0.0366 (15)	0.0439 (16)	0.102 (2)	−0.0010 (13)	0.0352 (16)	−0.0026 (16)
C50	0.0421 (16)	0.0385 (15)	0.086 (2)	0.0077 (12)	0.0284 (15)	−0.0023 (13)
C51	0.0411 (16)	0.0489 (17)	0.094 (3)	−0.0070 (12)	0.0208 (17)	−0.0182 (16)
C52	0.0401 (17)	0.0526 (17)	0.095 (2)	0.0091 (13)	0.0330 (16)	−0.0054 (16)
N3	0.0379 (12)	0.0271 (10)	0.0672 (15)	0.0036 (9)	0.0263 (11)	−0.0011 (9)
O41	0.0426 (11)	0.0301 (10)	0.138 (2)	0.0009 (9)	0.0438 (13)	−0.0023 (11)
O42	0.0481 (13)	0.0353 (11)	0.124 (2)	0.0050 (9)	0.0399 (14)	−0.0040 (11)
O43	0.0504 (14)	0.0443 (12)	0.166 (3)	0.0117 (10)	0.0500 (17)	−0.0096 (14)
C61	0.0403 (15)	0.0354 (13)	0.0528 (16)	−0.0049 (11)	0.0187 (13)	−0.0022 (11)
C62	0.0409 (14)	0.0365 (13)	0.0579 (17)	−0.0006 (11)	0.0167 (13)	0.0060 (12)
C63	0.0440 (15)	0.0406 (14)	0.0541 (16)	0.0000 (12)	0.0148 (13)	0.0023 (12)
C64	0.0454 (15)	0.0376 (14)	0.0648 (18)	−0.0070 (11)	0.0206 (14)	−0.0049 (12)
C65	0.0520 (16)	0.0375 (14)	0.067 (2)	−0.0064 (12)	0.0262 (16)	0.0011 (13)
C66	0.0562 (17)	0.0351 (14)	0.0647 (18)	0.0001 (12)	0.0279 (15)	0.0029 (12)
C67	0.0427 (16)	0.0385 (14)	0.0654 (18)	−0.0033 (11)	0.0273 (14)	−0.0005 (12)
C68	0.0423 (16)	0.0370 (14)	0.085 (2)	0.0015 (12)	0.0310 (15)	0.0033 (14)
C69	0.0459 (17)	0.0450 (17)	0.101 (3)	−0.0004 (14)	0.0351 (17)	0.0058 (17)
C70	0.0466 (17)	0.0437 (16)	0.078 (2)	−0.0024 (14)	0.0241 (15)	0.0061 (14)
C71	0.0435 (17)	0.0501 (17)	0.108 (3)	0.0048 (13)	0.0232 (18)	0.0119 (17)
C72	0.0508 (18)	0.0541 (19)	0.091 (3)	−0.0094 (15)	0.0245 (18)	−0.0014 (17)
N4	0.0408 (12)	0.0311 (11)	0.0658 (15)	0.0031 (9)	0.0220 (12)	0.0025 (9)
O61	0.0446 (11)	0.0361 (10)	0.1192 (19)	0.0011 (9)	0.0348 (12)	0.0126 (11)
O62	0.0484 (13)	0.0386 (11)	0.1059 (18)	0.0005 (9)	0.0288 (13)	0.0048 (11)
O63	0.0550 (15)	0.0537 (14)	0.164 (3)	−0.0110 (11)	0.0502 (17)	0.0081 (16)

C1—C6	1.378 (4)	C41—C42	1.384 (4)
C1—C2	1.390 (4)	C41—C46	1.397 (4)
C1—N1	1.423 (4)	C41—N3	1.420 (3)
C2—C3	1.399 (5)	C42—C43	1.374 (4)
C2—H2	0.93	C42—H42	0.93
C3—C4	1.385 (4)	C43—C44	1.389 (4)
C3—C11	1.505 (4)	C43—C51	1.516 (4)
C4—C5	1.395 (4)	C44—C45	1.379 (4)
C4—C12	1.498 (4)	C44—C52	1.518 (4)
C5—C6	1.388 (4)	C45—C46	1.386 (4)
C5—H5	0.93	C45—H45	0.93
C6—H6	0.93	C46—H46	0.93
C7—O1	1.237 (3)	C47—O41	1.232 (3)
C7—N1	1.341 (4)	C47—N3	1.343 (3)
C7—C8	1.483 (4)	C47—C48	1.483 (4)
C8—C9	1.322 (5)	C48—C49	1.320 (4)
C8—H8	0.93	C48—H48	0.93
C9—C10	1.505 (4)	C49—C50	1.493 (4)
C9—H9	0.93	C49—H49	0.93
C10—O3	1.206 (4)	C50—O43	1.214 (3)
C10—O2	1.306 (4)	C50—O42	1.283 (4)
C11—H11A	0.96	C51—H51A	0.96
C11—H11B	0.96	C51—H51B	0.96
C11—H11C	0.96	C51—H51C	0.96
C12—H12A	0.96	C52—H52A	0.96
C12—H12B	0.96	C52—H52B	0.96
C12—H12C	0.96	C52—H52C	0.96
C12—H12D	0.96	N3—H3N	0.86
C12—H12E	0.96	O42—H42A	0.88
C12—H12F	0.96	C61—C66	1.384 (4)
N1—H1	0.86	C61—C62	1.385 (4)
O2—H2A	0.88	C61—N4	1.426 (4)
C21—C26	1.384 (4)	C62—C63	1.398 (4)
C21—C22	1.395 (3)	C62—H62	0.93
C21—N2	1.420 (3)	C63—C64	1.400 (4)
C22—C23	1.394 (4)	C63—C71	1.494 (4)
C22—H22	0.93	C64—C65	1.413 (4)
C23—C24	1.406 (4)	C64—C72	1.502 (4)
C23—C31	1.500 (4)	C65—C66	1.377 (5)
C24—C25	1.390 (4)	C65—H65	0.93
C24—C32	1.505 (4)	C66—H66	0.93
C25—C26	1.375 (4)	C67—O61	1.243 (3)
C25—H25	0.93	C67—N4	1.333 (3)
C26—H26	0.93	C67—C68	1.479 (4)
C27—O21	1.247 (3)	C68—C69	1.321 (4)
C27—N2	1.332 (3)	C68—H68	0.93
C27—C28	1.483 (4)	C69—C70	1.493 (4)
C28—C29	1.343 (4)	C69—H69	0.93
C28—H28	0.93	C70—O63	1.203 (4)
C29—C30	1.467 (4)	C70—O62	1.299 (4)
C29—H29	0.93	C71—H71A	0.96
C30—O23	1.218 (4)	C71—H71B	0.96
C30—O22	1.301 (4)	C71—H71C	0.96
C31—H31A	0.96	C72—H72A	0.96
C31—H31B	0.96	C72—H72B	0.96
C31—H31C	0.96	C72—H72C	0.96
C32—H32A	0.96	C72—H72D	0.96
C32—H32B	0.96	C72—H72E	0.96
C32—H32C	0.96	C72—H72F	0.96
N2—H2N	0.86	N4—H4N	0.86
O22—H22A	0.88	O62—H62A	0.88
C6—C1—C2	119.2 (3)	C42—C41—C46	119.2 (2)
C6—C1—N1	116.0 (3)	C42—C41—N3	125.4 (2)
C2—C1—N1	124.8 (3)	C46—C41—N3	115.4 (2)
C1—C2—C3	120.2 (3)	C43—C42—C41	121.0 (2)
C1—C2—H2	119.9	C43—C42—H42	119.5
C3—C2—H2	119.9	C41—C42—H42	119.5
C4—C3—C2	120.5 (3)	C42—C43—C44	120.2 (2)
C4—C3—C11	121.0 (3)	C42—C43—C51	119.0 (2)
C2—C3—C11	118.5 (3)	C44—C43—C51	120.9 (2)
C3—C4—C5	118.9 (3)	C45—C44—C43	119.1 (2)
C3—C4—C12	121.6 (3)	C45—C44—C52	118.7 (2)
C5—C4—C12	119.5 (3)	C43—C44—C52	122.2 (3)
C6—C5—C4	120.4 (3)	C44—C45—C46	121.3 (2)
C6—C5—H5	119.8	C44—C45—H45	119.4
C4—C5—H5	119.8	C46—C45—H45	119.4
C1—C6—C5	120.8 (3)	C45—C46—C41	119.3 (2)
C1—C6—H6	119.6	C45—C46—H46	120.3
C5—C6—H6	119.6	C41—C46—H46	120.3
O1—C7—N1	123.5 (3)	O41—C47—N3	123.3 (3)
O1—C7—C8	122.9 (3)	O41—C47—C48	123.1 (2)
N1—C7—C8	113.6 (2)	N3—C47—C48	113.6 (2)
C9—C8—C7	128.5 (3)	C49—C48—C47	128.5 (3)
C9—C8—H8	115.8	C49—C48—H48	115.8
C7—C8—H8	115.8	C47—C48—H48	115.8
C8—C9—C10	131.9 (3)	C48—C49—C50	132.1 (3)
C8—C9—H9	114	C48—C49—H49	114
C10—C9—H9	114	C50—C49—H49	114
O3—C10—O2	121.1 (3)	O43—C50—O42	120.4 (3)
O3—C10—C9	119.2 (3)	O43—C50—C49	118.3 (3)
O2—C10—C9	119.6 (3)	O42—C50—C49	121.3 (3)
C3—C11—H11A	109.5	C43—C51—H51A	109.5
C3—C11—H11B	109.5	C43—C51—H51B	109.5
H11A—C11—H11B	109.5	H51A—C51—H51B	109.5
C3—C11—H11C	109.5	C43—C51—H51C	109.5
H11A—C11—H11C	109.5	H51A—C51—H51C	109.5
H11B—C11—H11C	109.5	H51B—C51—H51C	109.5
C4—C12—H12A	109.5	C44—C52—H52A	109.5
C4—C12—H12B	109.5	C44—C52—H52B	109.5
H12A—C12—H12B	109.5	H52A—C52—H52B	109.5
C4—C12—H12C	109.5	C44—C52—H52C	109.5
H12A—C12—H12C	109.5	H52A—C52—H52C	109.5
H12B—C12—H12C	109.5	H52B—C52—H52C	109.5
C4—C12—H12D	109.5	C47—N3—C41	127.8 (2)
H12A—C12—H12D	141.1	C47—N3—H3N	116.1
H12B—C12—H12D	56.3	C41—N3—H3N	116.1
H12C—C12—H12D	56.3	C50—O42—H42A	109.5
C4—C12—H12E	109.5	C66—C61—C62	120.1 (3)
H12A—C12—H12E	56.3	C66—C61—N4	116.0 (3)
H12B—C12—H12E	141.1	C62—C61—N4	123.9 (2)
H12C—C12—H12E	56.3	C61—C62—C63	120.2 (3)
H12D—C12—H12E	109.5	C61—C62—H62	119.9
C4—C12—H12F	109.5	C63—C62—H62	119.9
H12A—C12—H12F	56.3	C62—C63—C64	120.2 (3)
H12B—C12—H12F	56.3	C62—C63—C71	119.7 (3)
H12C—C12—H12F	141.1	C64—C63—C71	120.1 (3)
H12D—C12—H12F	109.5	C63—C64—C65	118.2 (3)
H12E—C12—H12F	109.5	C63—C64—C72	122.0 (3)
C7—N1—C1	128.4 (2)	C65—C64—C72	119.8 (3)
C7—N1—H1	115.8	C66—C65—C64	121.0 (3)
C1—N1—H1	115.8	C66—C65—H65	119.5
C10—O2—H2A	109.5	C64—C65—H65	119.5
C26—C21—C22	119.6 (2)	C65—C66—C61	120.2 (3)
C26—C21—N2	116.7 (2)	C65—C66—H66	119.9
C22—C21—N2	123.7 (2)	C61—C66—H66	119.9
C23—C22—C21	120.3 (2)	O61—C67—N4	122.8 (3)
C23—C22—H22	119.9	O61—C67—C68	123.0 (2)
C21—C22—H22	119.9	N4—C67—C68	114.3 (2)
C22—C23—C24	120.0 (2)	C69—C68—C67	128.4 (3)
C22—C23—C31	119.8 (2)	C69—C68—H68	115.8
C24—C23—C31	120.2 (2)	C67—C68—H68	115.8
C25—C24—C23	118.2 (2)	C68—C69—C70	132.8 (3)
C25—C24—C32	120.2 (3)	C68—C69—H69	113.6
C23—C24—C32	121.5 (2)	C70—C69—H69	113.6
C26—C25—C24	121.8 (3)	O63—C70—O62	122.1 (3)
C26—C25—H25	119.1	O63—C70—C69	118.0 (3)
C24—C25—H25	119.1	O62—C70—C69	119.9 (3)
C25—C26—C21	120.0 (2)	C63—C71—H71A	109.5
C25—C26—H26	120	C63—C71—H71B	109.5
C21—C26—H26	120	H71A—C71—H71B	109.5
O21—C27—N2	123.2 (3)	C63—C71—H71C	109.5
O21—C27—C28	122.7 (2)	H71A—C71—H71C	109.5
N2—C27—C28	114.1 (2)	H71B—C71—H71C	109.5
C29—C28—C27	127.6 (3)	C64—C72—H72A	109.5
C29—C28—H28	116.2	C64—C72—H72B	109.5
C27—C28—H28	116.2	H72A—C72—H72B	109.5
C28—C29—C30	132.9 (3)	C64—C72—H72C	109.5
C28—C29—H29	113.6	H72A—C72—H72C	109.5
C30—C29—H29	113.6	H72B—C72—H72C	109.5
O23—C30—O22	120.5 (3)	C64—C72—H72D	109.5
O23—C30—C29	119.1 (3)	H72A—C72—H72D	141.1
O22—C30—C29	120.3 (3)	H72B—C72—H72D	56.3
C23—C31—H31A	109.5	H72C—C72—H72D	56.3
C23—C31—H31B	109.5	C64—C72—H72E	109.5
H31A—C31—H31B	109.5	H72A—C72—H72E	56.3
C23—C31—H31C	109.5	H72B—C72—H72E	141.1
H31A—C31—H31C	109.5	H72C—C72—H72E	56.3
H31B—C31—H31C	109.5	H72D—C72—H72E	109.5
C24—C32—H32A	109.5	C64—C72—H72F	109.5
C24—C32—H32B	109.5	H72A—C72—H72F	56.3
H32A—C32—H32B	109.5	H72B—C72—H72F	56.3
C24—C32—H32C	109.5	H72C—C72—H72F	141.1
H32A—C32—H32C	109.5	H72D—C72—H72F	109.5
H32B—C32—H32C	109.5	H72E—C72—H72F	109.5
C27—N2—C21	128.7 (2)	C67—N4—C61	129.3 (2)
C27—N2—H2N	115.7	C67—N4—H4N	115.4
C21—N2—H2N	115.7	C61—N4—H4N	115.4
C30—O22—H22A	109.5	C70—O62—H62A	109.5
C6—C1—C2—C3	−1.3 (4)	C46—C41—C42—C43	2.2 (4)
N1—C1—C2—C3	179.2 (3)	N3—C41—C42—C43	179.5 (3)
C1—C2—C3—C4	0.9 (4)	C41—C42—C43—C44	−1.8 (4)
C1—C2—C3—C11	−179.8 (3)	C41—C42—C43—C51	177.8 (3)
C2—C3—C4—C5	−0.6 (4)	C42—C43—C44—C45	0.0 (4)
C11—C3—C4—C5	−179.9 (3)	C51—C43—C44—C45	−179.6 (3)
C2—C3—C4—C12	179.8 (3)	C42—C43—C44—C52	178.8 (3)
C11—C3—C4—C12	0.4 (4)	C51—C43—C44—C52	−0.8 (4)
C3—C4—C5—C6	0.6 (5)	C43—C44—C45—C46	1.4 (5)
C12—C4—C5—C6	−179.7 (3)	C52—C44—C45—C46	−177.4 (3)
C2—C1—C6—C5	1.4 (4)	C44—C45—C46—C41	−1.0 (5)
N1—C1—C6—C5	−179.1 (3)	C42—C41—C46—C45	−0.8 (4)
C4—C5—C6—C1	−1.1 (5)	N3—C41—C46—C45	−178.4 (3)
O1—C7—C8—C9	−13.3 (6)	O41—C47—C48—C49	1.8 (6)
N1—C7—C8—C9	167.3 (4)	N3—C47—C48—C49	−177.6 (4)
C7—C8—C9—C10	2.3 (8)	C47—C48—C49—C50	1.4 (7)
C8—C9—C10—O3	−171.1 (4)	C48—C49—C50—O43	−179.9 (4)
C8—C9—C10—O2	10.9 (7)	C48—C49—C50—O42	−0.4 (7)
O1—C7—N1—C1	6.8 (5)	O41—C47—N3—C41	−1.5 (5)
C8—C7—N1—C1	−173.9 (3)	C48—C47—N3—C41	178.0 (3)
C6—C1—N1—C7	159.6 (3)	C42—C41—N3—C47	18.9 (4)
C2—C1—N1—C7	−20.9 (5)	C46—C41—N3—C47	−163.7 (3)
C26—C21—C22—C23	−0.1 (4)	C66—C61—C62—C63	−1.0 (5)
N2—C21—C22—C23	−179.9 (2)	N4—C61—C62—C63	179.1 (3)
C21—C22—C23—C24	−0.8 (4)	C61—C62—C63—C64	0.1 (5)
C21—C22—C23—C31	180.0 (3)	C61—C62—C63—C71	178.8 (3)
C22—C23—C24—C25	1.4 (4)	C62—C63—C64—C65	0.5 (5)
C31—C23—C24—C25	−179.3 (3)	C71—C63—C64—C65	−178.2 (3)
C22—C23—C24—C32	−178.0 (3)	C62—C63—C64—C72	179.6 (3)
C31—C23—C24—C32	1.3 (4)	C71—C63—C64—C72	1.0 (5)
C23—C24—C25—C26	−1.2 (5)	C63—C64—C65—C66	−0.2 (5)
C32—C24—C25—C26	178.2 (3)	C72—C64—C65—C66	−179.3 (3)
C24—C25—C26—C21	0.3 (5)	C64—C65—C66—C61	−0.7 (5)
C22—C21—C26—C25	0.4 (4)	C62—C61—C66—C65	1.3 (5)
N2—C21—C26—C25	−179.9 (3)	N4—C61—C66—C65	−178.8 (3)
O21—C27—C28—C29	−9.7 (6)	O61—C67—C68—C69	7.0 (6)
N2—C27—C28—C29	170.8 (4)	N4—C67—C68—C69	−173.2 (4)
C27—C28—C29—C30	−0.3 (7)	C67—C68—C69—C70	1.3 (8)
C28—C29—C30—O23	−170.8 (4)	C68—C69—C70—O63	175.1 (5)
C28—C29—C30—O22	9.5 (7)	C68—C69—C70—O62	−3.2 (7)
O21—C27—N2—C21	7.0 (5)	O61—C67—N4—C61	−0.3 (5)
C28—C27—N2—C21	−173.6 (3)	C68—C67—N4—C61	179.8 (3)
C26—C21—N2—C27	155.7 (3)	C66—C61—N4—C67	−168.4 (3)
C22—C21—N2—C27	−24.5 (4)	C62—C61—N4—C67	11.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O63i	0.86	2.00	2.851 (3)	168
N2—H2N···O43	0.86	2.03	2.865 (3)	163
N3—H3N···O23i	0.86	2.07	2.916 (3)	167
N4—H4N···O3	0.86	2.08	2.930 (3)	169
O2—H2A···O1	0.88	1.62	2.481 (3)	165
O22—H22A···O21	0.88	1.59	2.471 (3)	176
O42—H42A···O41	0.88	1.61	2.487 (3)	175
O62—H62A···O61	0.88	1.6	2.480 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O63i	0.86	2.00	2.851 (3)	168
N2—H2N⋯O43	0.86	2.03	2.865 (3)	163
N3—H3N⋯O23i	0.86	2.07	2.916 (3)	167
N4—H4N⋯O3	0.86	2.08	2.930 (3)	169
O2—H2A⋯O1	0.88	1.62	2.481 (3)	165
O22—H22A⋯O21	0.88	1.59	2.471 (3)	176
O42—H42A⋯O41	0.88	1.61	2.487 (3)	175
O62—H62A⋯O61	0.88	1.6	2.480 (3)	176

Symmetry code: (i) .