4-(3,4-Dimethoxy­phen­yl)-2-oxo-N,3-bis­(3,4,5-trimethoxy­phenyl)-2,3-dihydro-1H-imidazoline-1-carboxamide

The structure of the title compound, C₃₀H₃₃N₃O₁₀, consists of an almost planar imidazolin-2-one system connecting two planar substituted phenyl groups and a roughly planar 3,4,5-trimethoxy­anilinocarbonyl fragment which forms a dihedral angle of 95.17 (9)° with the heterocyclic ring.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.057
• wR factor = 0.131
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O6     -   C20     ..      11.13 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O10    -   C30     ..       7.64 su

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.660
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.66 e/A   3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   C15     ..       5.80 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    -   C17     ..       5.78 su

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Imidazolones, in particular aryl-substituted imidazolin-2-ones, have become attractive targets for organic synthesis because of their broad spectrum of biological activities, being reported as antioxidants (Smith et al., 1987), ATP-sensitive potassium channel openers (Gadwood et al., 1995) and anti-inflammatory phosphodiesterse PDE4 inhibitors (Andrés et al., 2002). Additionally, they are widely used in combinatorial chemistry to search for pharmacologically active agents (Durant, 1985). In order to study their potential biological activity in other areas, a series of imidazolin-2-ones have been synthesized and evaluated for antitumour activity in vitro against a human tumour cell line (leukaemia HL-60). The title compound, (I), has a low micromolar IC50 of 6.5 µmol l⁻¹ against leukaemia HL-60. To confirm its conformation in the crystal, an X-ray study of (I) has been carried out and the results are presented here (Fig. 1 and Table 1).

The roughly coplanar arrangement of the imidazolin-2-one and carboxamide groups may be further stabilized by an intramolecular N1—H1···O2 contact (H1···O2 = 1.97 Å and N1—H1···O2 = 142°).

S2. Experimental

3,4,5-Trimethoxyaniline (3 mmol) in dry toluene (4 ml) was added dropwise to a stirred solution of (COCl₂)₃ (2.91 mmol) in dry toluene (4 ml) and cooled in an ice bath. After stirring for 1 h at room temperature and refluxing for 4 h, 3,4-dimethoxy-ω-aminoacetophenone (3 mmol) was added to the mixture directly and it was then heated under reflux overnight. After removal of the toluene, the residue was extracted with dichloromethane and dried over anhydrous sodium sulfate. After removing the solvent in vacuo, the residue was purified by column chromatography (silica gel, trichloromethane–petroleum ether = 1:1) to afford the title compound. Crystals of (I) suitable for crystallographic study were obtained by slow crystallization from ethyl acetate at room temperature.

S3. Refinement

All H atoms were positioned geometrically. The methyl H atoms were then constrained to an ideal geometry, with C—H = 0.96 Å and U_iso(H) = 1.2U_eq(C), but each group was allowed to rotate freely about its C—C bond. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.98 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: Please provide missing information; software used to prepare material for publication: CrystalStructure.

Figures

Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 40% probability level.

4-(3,4-Dimethoxyphenyl)-2-oxo-N,3-bis(3,4,5-trimethoxyphenyl)- 2,3-dihydro-1H-imidazoline-1-carboxamide

Crystal data

C30H33N3O10	Z = 2
Mr = 595.60	F(000) = 628.00
Triclinic, P1	Dx = 1.337 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 9.429 (4) Å	Cell parameters from 11137 reflections
b = 11.209 (4) Å	θ = 3.0–27.5°
c = 15.890 (7) Å	µ = 0.10 mm^−1
α = 93.802 (15)°	T = 296 K
β = 104.333 (16)°	Platelet, colourless
γ = 112.476 (14)°	0.33 × 0.20 × 0.10 mm
V = 1479.1 (10) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	4056 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.027
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.961, Tmax = 0.990	k = −14→13
14714 measured reflections	l = −20→20
6711 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0002Fo^2 + 3σ(Fo^2) + 0.5]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.057	(Δ/σ)max < 0.001
wR(F^2) = 0.131	Δρmax = 0.66 e Å^−3
S = 1.01	Δρmin = −0.54 e Å^−3
6711 reflections	Extinction correction: Larson (1970), equation 22
440 parameters	Extinction coefficient: 391 (28)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	1.19868 (18)	0.32905 (13)	0.56873 (9)	0.0559 (4)
O2	0.73770 (18)	0.19091 (14)	0.38843 (10)	0.0576 (4)
O3	1.2779 (2)	0.90176 (17)	0.19154 (12)	0.0760 (6)
O4	1.0331 (2)	0.68805 (19)	0.09811 (11)	0.0908 (6)
O5	0.4105 (2)	0.46062 (18)	0.18159 (12)	0.0712 (6)
O6	0.3721 (2)	0.30681 (17)	0.03581 (11)	0.0712 (5)
O7	0.5696 (2)	0.18927 (17)	0.02900 (10)	0.0685 (5)
O8	0.70884 (19)	−0.25109 (14)	0.61772 (11)	0.0639 (5)
O9	0.9730 (2)	−0.19225 (16)	0.75159 (11)	0.0667 (5)
O10	1.2234 (2)	0.03984 (17)	0.78497 (11)	0.0715 (5)
N1	0.9495 (2)	0.15864 (16)	0.52388 (11)	0.0447 (5)
N2	1.0086 (2)	0.33408 (16)	0.45135 (10)	0.0428 (4)
N3	0.8696 (2)	0.37810 (16)	0.33520 (10)	0.0420 (4)
C1	1.0624 (2)	0.2741 (2)	0.52057 (12)	0.0422 (6)
C2	1.1096 (2)	0.4484 (2)	0.43102 (12)	0.0456 (5)
C3	1.0268 (2)	0.47807 (19)	0.36002 (12)	0.0407 (5)
C4	0.8567 (2)	0.2890 (2)	0.39046 (12)	0.0432 (6)
C5	1.0863 (2)	0.5892 (2)	0.31574 (12)	0.0413 (5)
C6	1.2124 (2)	0.7034 (2)	0.36410 (13)	0.0486 (6)
C7	1.2799 (2)	0.8085 (2)	0.32495 (16)	0.0547 (6)
C8	1.2217 (2)	0.8035 (2)	0.23630 (16)	0.0527 (7)
C9	1.0912 (2)	0.6899 (2)	0.18645 (16)	0.0626 (7)
C10	1.0266 (2)	0.5851 (2)	0.22596 (14)	0.0570 (6)
C11	1.4037 (4)	1.0214 (2)	0.2415 (2)	0.0897 (10)
C12	0.8992 (6)	0.5722 (4)	0.0447 (2)	0.1147 (18)
C13	0.7373 (2)	0.35873 (19)	0.25816 (12)	0.0397 (5)
C14	0.6402 (2)	0.4216 (2)	0.26230 (13)	0.0465 (6)
C15	0.5145 (2)	0.4022 (2)	0.18630 (16)	0.0496 (6)
C16	0.4927 (2)	0.3229 (2)	0.10944 (14)	0.0507 (6)
C17	0.5968 (2)	0.2624 (2)	0.10780 (13)	0.0486 (6)
C18	0.7176 (2)	0.2779 (2)	0.18322 (12)	0.0433 (5)
C19	0.4076 (3)	0.5238 (2)	0.2614 (2)	0.0817 (10)
C20	0.2443 (5)	0.1699 (4)	0.0024 (3)	0.0955 (18)
C21	0.6837 (3)	0.1408 (2)	0.02096 (17)	0.0823 (10)
C22	0.9599 (2)	0.0747 (2)	0.58456 (12)	0.0431 (6)
C23	0.8296 (2)	−0.0436 (2)	0.56983 (13)	0.0471 (6)
C24	0.8318 (2)	−0.1316 (2)	0.62617 (13)	0.0477 (6)
C25	0.9683 (2)	−0.1018 (2)	0.69772 (13)	0.0487 (6)
C26	1.0966 (2)	0.0175 (2)	0.71245 (13)	0.0502 (6)
C27	1.0968 (2)	0.1068 (2)	0.65609 (12)	0.0497 (6)
C28	0.5643 (2)	−0.2853 (2)	0.54888 (17)	0.0734 (8)
C29	0.9108 (3)	−0.1828 (2)	0.82290 (19)	0.0836 (10)
C30	1.3567 (3)	0.1639 (2)	0.80529 (18)	0.0929 (10)
H1	0.8588	0.1326	0.4837	0.053*
H2	1.2173	0.4971	0.4619	0.050*
H6	1.2535	0.7094	0.4246	0.057*
H7	1.3664	0.8838	0.3591	0.063*
H10	0.9410	0.5095	0.1917	0.061*
H14	0.6564	0.4755	0.3140	0.057*
H18	0.7845	0.2348	0.1833	0.051*
H23	0.7394	−0.0641	0.5217	0.057*
H27	1.1851	0.1866	0.6660	0.057*
H111	1.3718	1.0526	0.2883	0.108*
H112	1.4984	1.0072	0.2662	0.108*
H113	1.4259	1.0855	0.2039	0.108*
H121	0.8111	0.5582	0.0684	0.113*
H122	0.8693	0.5837	−0.0155	0.113*
H123	0.9256	0.4976	0.0469	0.113*
H191	0.3446	0.5739	0.2484	0.109*
H192	0.3614	0.4586	0.2945	0.110*
H193	0.5155	0.5811	0.2954	0.110*
H201	0.2552	0.1174	0.0469	0.109*
H202	0.1401	0.1714	−0.0103	0.109*
H203	0.2561	0.1329	−0.0503	0.110*
H211	0.6967	0.0898	0.0661	0.097*
H212	0.7846	0.2130	0.0276	0.097*
H213	0.6479	0.0867	−0.0360	0.096*
H281	0.4876	−0.3699	0.5516	0.081*
H282	0.5222	−0.2209	0.5560	0.081*
H283	0.5849	−0.2878	0.4927	0.081*
H291	0.9701	−0.0968	0.8586	0.104*
H292	0.9196	−0.2474	0.8582	0.104*
H293	0.7999	−0.1982	0.8001	0.104*
H301	1.4300	0.1723	0.8617	0.097*
H302	1.4106	0.1711	0.7607	0.098*
H303	1.3193	0.2323	0.8072	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0499 (9)	0.0583 (9)	0.0450 (8)	0.0169 (7)	−0.0027 (7)	0.0114 (7)
O2	0.0410 (9)	0.0623 (9)	0.0571 (9)	0.0117 (8)	0.0052 (7)	0.0261 (7)
O3	0.0821 (13)	0.0623 (10)	0.0745 (11)	0.0121 (10)	0.0320 (10)	0.0291 (9)
O4	0.0840 (14)	0.0860 (13)	0.0556 (11)	−0.0036 (11)	−0.0014 (9)	0.0326 (10)
O5	0.0610 (11)	0.0940 (13)	0.0809 (12)	0.0491 (10)	0.0257 (9)	0.0357 (10)
O6	0.0517 (10)	0.0787 (11)	0.0612 (10)	0.0182 (9)	−0.0098 (8)	0.0250 (9)
O7	0.0642 (11)	0.0854 (12)	0.0424 (9)	0.0282 (10)	0.0003 (8)	−0.0007 (8)
O8	0.0532 (10)	0.0604 (10)	0.0679 (11)	0.0168 (8)	0.0085 (8)	0.0230 (8)
O9	0.0706 (11)	0.0725 (11)	0.0678 (11)	0.0384 (9)	0.0184 (9)	0.0360 (9)
O10	0.0624 (11)	0.0773 (11)	0.0541 (9)	0.0191 (9)	−0.0059 (8)	0.0256 (8)
N1	0.0410 (10)	0.0543 (10)	0.0369 (9)	0.0210 (9)	0.0045 (8)	0.0134 (8)
N2	0.0409 (10)	0.0477 (10)	0.0352 (9)	0.0167 (8)	0.0053 (7)	0.0110 (7)
N3	0.0377 (9)	0.0480 (9)	0.0365 (9)	0.0160 (8)	0.0061 (7)	0.0122 (7)
C1	0.0462 (13)	0.0498 (12)	0.0333 (10)	0.0254 (11)	0.0068 (9)	0.0079 (9)
C2	0.0409 (12)	0.0438 (11)	0.0420 (11)	0.0118 (10)	0.0047 (9)	0.0069 (9)
C3	0.0352 (11)	0.0448 (11)	0.0386 (11)	0.0161 (9)	0.0060 (9)	0.0065 (9)
C4	0.0413 (12)	0.0517 (12)	0.0372 (11)	0.0218 (11)	0.0075 (9)	0.0118 (9)
C5	0.0356 (11)	0.0471 (11)	0.0437 (11)	0.0197 (9)	0.0110 (9)	0.0112 (9)
C6	0.0486 (13)	0.0506 (12)	0.0435 (12)	0.0205 (11)	0.0081 (10)	0.0084 (10)
C7	0.0516 (14)	0.0459 (12)	0.0594 (14)	0.0137 (11)	0.0151 (11)	0.0072 (11)
C8	0.0487 (13)	0.0522 (13)	0.0602 (14)	0.0179 (11)	0.0232 (11)	0.0212 (11)
C9	0.0545 (15)	0.0753 (16)	0.0481 (13)	0.0161 (13)	0.0122 (11)	0.0254 (12)
C10	0.0453 (13)	0.0592 (14)	0.0464 (13)	0.0053 (11)	0.0047 (10)	0.0134 (11)
C11	0.112 (2)	0.0546 (16)	0.102 (2)	0.0179 (16)	0.0545 (19)	0.0259 (15)
C12	0.122 (4)	0.109 (4)	0.050 (2)	0.004 (3)	−0.016 (2)	0.033 (2)
C13	0.0323 (10)	0.0455 (11)	0.0392 (11)	0.0154 (9)	0.0062 (8)	0.0149 (9)
C14	0.0447 (12)	0.0498 (12)	0.0467 (12)	0.0188 (10)	0.0155 (10)	0.0154 (10)
C15	0.0355 (11)	0.0585 (13)	0.0654 (15)	0.0256 (10)	0.0177 (10)	0.0311 (11)
C16	0.0352 (11)	0.0654 (14)	0.0475 (13)	0.0186 (11)	0.0050 (10)	0.0254 (11)
C17	0.0446 (12)	0.0503 (12)	0.0382 (11)	0.0095 (10)	0.0065 (9)	0.0112 (10)
C18	0.0384 (11)	0.0466 (11)	0.0436 (11)	0.0176 (9)	0.0080 (9)	0.0147 (9)
C19	0.077 (2)	0.087 (2)	0.110 (2)	0.0540 (17)	0.0399 (18)	0.0313 (17)
C20	0.077 (3)	0.125 (4)	0.069 (3)	0.037 (3)	0.005 (2)	0.004 (3)
C21	0.085 (2)	0.098 (2)	0.0576 (16)	0.0351 (19)	0.0188 (15)	−0.0027 (15)
C22	0.0478 (12)	0.0525 (12)	0.0360 (10)	0.0277 (11)	0.0117 (9)	0.0119 (9)
C23	0.0411 (12)	0.0592 (13)	0.0411 (11)	0.0240 (11)	0.0062 (9)	0.0110 (10)
C24	0.0472 (13)	0.0500 (12)	0.0485 (12)	0.0214 (11)	0.0158 (10)	0.0118 (10)
C25	0.0524 (13)	0.0574 (13)	0.0467 (12)	0.0315 (11)	0.0152 (10)	0.0206 (10)
C26	0.0489 (13)	0.0655 (14)	0.0385 (11)	0.0298 (12)	0.0054 (10)	0.0147 (10)
C27	0.0486 (13)	0.0556 (13)	0.0399 (11)	0.0201 (11)	0.0058 (10)	0.0125 (10)
C28	0.0534 (16)	0.0740 (17)	0.0738 (18)	0.0124 (13)	0.0083 (13)	0.0162 (14)
C29	0.080 (2)	0.107 (2)	0.0736 (19)	0.0409 (18)	0.0252 (16)	0.0494 (17)
C30	0.0692 (19)	0.105 (2)	0.0700 (18)	0.0207 (17)	−0.0165 (15)	0.0248 (16)

Geometric parameters (Å, º)

O1—C1	1.209 (2)	C22—C23	1.376 (2)
O2—C4	1.226 (2)	C22—C27	1.397 (2)
O3—C8	1.358 (3)	C23—C24	1.377 (3)
O3—C11	1.419 (2)	C24—C25	1.399 (2)
O4—C9	1.370 (2)	C25—C26	1.374 (2)
O4—C12	1.439 (4)	C26—C27	1.387 (3)
O5—C15	1.362 (3)	N1—H1	0.860
O5—C19	1.422 (4)	C2—H2	0.930
O6—C16	1.360 (2)	C6—H6	0.930
O6—C20	1.500 (4)	C7—H7	0.930
O7—C17	1.360 (2)	C10—H10	0.930
O7—C21	1.405 (4)	C11—H111	0.960
O8—C24	1.367 (2)	C11—H112	0.960
O8—C28	1.417 (2)	C11—H113	0.960
O9—C25	1.376 (3)	C12—H121	0.959
O9—C29	1.414 (4)	C12—H122	0.961
O10—C26	1.367 (2)	C12—H123	0.960
O10—C30	1.422 (2)	C14—H14	0.930
N1—C1	1.339 (2)	C18—H18	0.930
N1—C22	1.403 (2)	C19—H191	0.960
N2—C1	1.415 (2)	C19—H192	0.960
N2—C2	1.388 (2)	C19—H193	0.960
N2—C4	1.392 (2)	C20—H201	0.960
N3—C3	1.411 (2)	C20—H202	0.960
N3—C4	1.364 (2)	C20—H203	0.960
N3—C13	1.450 (2)	C21—H211	0.960
C2—C3	1.344 (3)	C21—H212	0.960
C3—C5	1.462 (2)	C21—H213	0.960
C5—C6	1.377 (2)	C23—H23	0.930
C5—C10	1.389 (3)	C27—H27	0.930
C6—C7	1.379 (3)	C28—H281	0.960
C7—C8	1.368 (3)	C28—H282	0.960
C8—C9	1.396 (2)	C28—H283	0.960
C9—C10	1.372 (3)	C29—H291	0.960
C13—C14	1.363 (3)	C29—H292	0.960
C13—C18	1.375 (3)	C29—H293	0.960
C14—C15	1.404 (2)	C30—H301	0.960
C15—C16	1.384 (3)	C30—H302	0.960
C16—C17	1.394 (4)	C30—H303	0.960
C17—C18	1.381 (2)
O1···O8^i	3.438 (2)	H18···H113^iii	3.262
O1···C14^ii	3.327 (2)	H18···H291^i	3.399
O1···C24^i	3.569 (2)	H18···H292^i	2.976
O1···C28^i	3.393 (3)	H23···O1^i	3.522
O2···C11^iii	3.190 (2)	H23···H7^ii	3.261
O3···C21^iv	3.505 (3)	H23···H27^i	3.541
O5···C29^v	3.396 (3)	H23···H111^ii	3.442
O6···C12^vi	3.359 (6)	H27···H14^ii	3.457
O7···C21^vii	3.455 (3)	H27···H23^i	3.541
O7···C30^viii	3.556 (3)	H27···H193^ii	2.905
O8···O1^i	3.438 (2)	H111···O2^x	3.115
O8···N2^i	3.518 (2)	H111···O8^ii	3.029
O8···C1^i	3.499 (3)	H111···C23^ii	3.271
O8···C2^i	3.427 (3)	H111···C24^ii	2.957
O9···N2^i	3.573 (2)	H111···C25^ii	3.511
O9···N3^i	3.382 (3)	H111···C28^ii	3.315
O9···C3^i	3.558 (3)	H111···H23^ii	3.442
O9···C4^i	3.413 (3)	H111···H282^ii	2.719
O9···C18^i	3.359 (3)	H111···H293^ii	2.909
O10···C20^ix	3.588 (5)	H112···O2^x	2.618
N1···C6^ii	3.267 (3)	H112···O10^xi	3.143
N1···C22^i	3.518 (3)	H112···C18^x	3.508
N1···C23^i	3.399 (3)	H112···C30^xi	3.053
N1···C24^i	3.584 (3)	H112···H18^x	3.531
N2···O8^i	3.518 (2)	H112···H213^iv	3.502
N2···O9^i	3.573 (2)	H112···H301^xi	3.131
N2···C24^i	3.478 (3)	H112···H302^xi	2.508
N2···C25^i	3.508 (3)	H113···O2^x	3.354
N3···O9^i	3.382 (3)	H113···O7^x	3.464
C1···O8^i	3.499 (3)	H113···C13^x	3.204
C1···C6^ii	3.596 (3)	H113···C14^x	3.453
C1···C23^i	3.466 (3)	H113···C15^x	3.370
C1···C24^i	3.295 (3)	H113···C16^x	3.074
C2···O8^i	3.427 (3)	H113···C17^x	2.835
C3···O9^i	3.558 (3)	H113···C18^x	2.886
C4···O9^i	3.413 (3)	H113···H18^x	3.262
C4···C25^i	3.534 (4)	H113···H201^x	2.741
C6···N1^ii	3.267 (3)	H113···H213^iv	2.949
C6···C1^ii	3.596 (3)	H113···H293^ii	2.852
C7···C22^ii	3.538 (4)	H121···O6^vi	2.989
C11···O2^x	3.190 (2)	H121···C20^vi	3.494
C12···O6^vi	3.359 (6)	H121···H202^vi	3.125
C12···C12^iv	3.411 (9)	H122···O5^vi	3.090
C14···O1^ii	3.327 (2)	H122···O6^vi	2.936
C18···O9^i	3.359 (3)	H122···C12^iv	3.368
C20···O10^viii	3.588 (5)	H122···C20^vi	3.334
C20···C29^v	3.462 (6)	H122···H122^iv	3.591
C20···C30^viii	3.551 (6)	H122···H123^iv	2.566
C21···O3^iv	3.505 (3)	H122···H202^vi	2.786
C21···O7^vii	3.455 (3)	H122···H212^iv	3.249
C21···C21^vii	3.553 (3)	H122···H292^xiii	2.850
C22···N1^i	3.518 (3)	H123···O4^iv	3.197
C22···C7^ii	3.538 (4)	H123···C12^iv	2.737
C22···C22^i	3.460 (3)	H123···H122^iv	2.566
C22···C23^i	3.593 (3)	H123···H123^iv	2.277
C23···N1^i	3.399 (3)	H191···C5^xiv	2.948
C23···C1^i	3.466 (3)	H191···C6^xiv	3.034
C23···C22^i	3.593 (3)	H191···C7^xiv	3.152
C24···O1^i	3.569 (2)	H191···C8^xiv	3.199
C24···N1^i	3.584 (3)	H191···C9^xiv	3.122
C24···N2^i	3.478 (3)	H191···C10^xiv	2.983
C24···C1^i	3.295 (3)	H191···C30^ii	3.534
C25···N2^i	3.508 (3)	H191···H6^xiv	3.536
C25···C4^i	3.534 (4)	H191···H10^xiv	3.454
C28···O1^i	3.393 (3)	H191···H292^v	3.548
C29···O5^v	3.396 (3)	H191···H302^ii	2.949
C29···C20^v	3.462 (6)	H191···H303^ii	3.453
C30···O7^ix	3.556 (3)	H192···O8^v	2.739
C30···C20^ix	3.551 (6)	H192···O9^v	3.281
O1···H14^ii	2.459	H192···C2^xiv	3.568
O1···H23^i	3.522	H192···C5^xiv	3.501
O1···H193^ii	2.774	H192···C28^v	3.358
O1···H281^x	3.513	H192···C29^v	3.229
O1···H283^i	2.642	H192···H2^xiv	3.345
O2···H6^ii	3.074	H192···H281^v	2.945
O2···H111^iii	3.115	H192···H292^v	3.126
O2···H112^iii	2.618	H192···H293^v	2.826
O2···H113^iii	3.354	H193···O1^ii	2.774
O2···H282^v	2.925	H193···C30^ii	3.333
O3···H201^x	3.473	H193···H27^ii	2.905
O3···H212^iv	3.455	H193···H281^v	3.502
O3···H213^iv	2.727	H193···H283^xv	3.172
O3···H301^xi	3.435	H193···H302^ii	2.855
O3···H302^xi	3.268	H193···H303^ii	2.946
O4···H123^iv	3.197	H201···O3^iii	3.473
O4···H202^vi	2.868	H201···C11^iii	3.483
O4···H212^iv	2.952	H201···C21^vii	3.323
O4···H213^iv	3.519	H201···C29^v	3.091
O5···H122^vi	3.090	H201···H113^iii	2.741
O5···H292^v	2.990	H201···H211^vii	3.078
O5···H293^v	2.934	H201···H213^vii	2.779
O5···H303^ii	3.370	H201···H291^viii	3.475
O6···H121^vi	2.989	H201···H291^v	2.841
O6···H122^vi	2.936	H201···H292^v	3.145
O6···H292^v	3.448	H201···H293^v	2.774
O6···H293^v	3.452	H202···O4^vi	2.868
O6···H301^viii	3.324	H202···C12^vi	3.101
O6···H303^viii	3.539	H202···C29^v	3.133
O7···H113^iii	3.464	H202···H121^vi	3.125
O7···H211^vii	3.140	H202···H122^vi	2.786
O7···H213^vii	3.016	H202···H291^viii	3.128
O7···H301^viii	2.617	H202···H291^v	2.904
O8···H2^i	3.336	H202···H292^v	2.766
O8···H111^ii	3.029	H202···H293^v	3.220
O8···H192^v	2.739	H203···O10^viii	2.650
O9···H18^i	2.501	H203···C21^vii	3.369
O9···H192^v	3.281	H203···C30^viii	2.686
O9···H211^i	3.431	H203···H211^vii	2.704
O10···H18^i	3.129	H203···H213^vii	3.210
O10···H112^xi	3.143	H203···H291^viii	2.875
O10···H203^ix	2.650	H203···H301^viii	2.345
O10···H211^i	2.948	H203···H303^viii	2.686
N1···H6^ii	3.050	H211···O7^vii	3.140
N2···H6^ii	3.443	H211···O9^i	3.431
C1···H6^ii	3.370	H211···O10^i	2.948
C1···H14^ii	3.420	H211···C20^vii	3.329
C1···H283^i	3.329	H211···C21^vii	3.382
C2···H192^xii	3.568	H211···C29^i	3.387
C2···H281^x	3.328	H211···C30^i	3.564
C4···H6^ii	3.353	H211···H201^vii	3.078
C5···H191^xii	2.948	H211···H203^vii	2.704
C5···H192^xii	3.501	H211···H211^vii	3.478
C6···H1^ii	3.292	H211···H213^vii	2.982
C6···H191^xii	3.034	H211···H291^i	3.041
C6···H282^x	3.450	H211···H292^i	3.215
C6···H283^x	3.561	H211···H301^i	3.133
C7···H191^xii	3.152	H212···O3^iv	3.455
C7···H302^xi	3.453	H212···O4^iv	2.952
C8···H191^xii	3.199	H212···C12^iv	3.547
C8···H302^xi	3.357	H212···C29^i	3.388
C9···H191^xii	3.122	H212···H122^iv	3.249
C10···H191^xii	2.983	H212···H291^i	3.296
C11···H201^x	3.483	H212···H292^i	2.794
C11···H213^iv	3.257	H212···H301^viii	3.557
C11···H282^ii	3.546	H213···O3^iv	2.727
C11···H293^ii	3.241	H213···O4^iv	3.519
C11···H302^xi	3.261	H213···O7^vii	3.016
C12···H122^iv	3.368	H213···C11^iv	3.257
C12···H123^iv	2.737	H213···C20^vii	3.430
C12···H202^vi	3.101	H213···C21^vii	3.270
C12···H212^iv	3.547	H213···H112^iv	3.502
C13···H113^iii	3.204	H213···H113^iv	2.949
C14···H113^iii	3.453	H213···H201^vii	2.779
C14···H281^v	3.463	H213···H203^vii	3.210
C15···H113^iii	3.370	H213···H211^vii	2.982
C15···H293^v	3.043	H213···H213^vii	3.256
C16···H113^iii	3.074	H213···H301^viii	2.801
C16···H293^v	3.304	H281···O1^iii	3.513
C17···H113^iii	2.835	H281···C2^iii	3.328
C18···H112^iii	3.508	H281···C14^v	3.463
C18···H113^iii	2.886	H281···H2^iii	2.401
C19···H292^v	3.425	H281···H6^iii	3.045
C19···H293^v	3.349	H281···H14^v	2.890
C19···H302^ii	3.277	H281···H192^v	2.945
C19···H303^ii	3.420	H281···H193^v	3.502
C20···H121^vi	3.494	H281···H281	3.364
C20···H122^vi	3.334	H282···O2^v	2.925
C20···H211^vii	3.329	H282···C6^iii	3.450
C20···H213^vii	3.430	H282···C11^ii	3.546
C20···H291^viii	3.332	H282···H2^iii	3.284
C20···H291^v	3.290	H282···H6^iii	2.654
C20···H292^v	3.243	H282···H7^iii	3.586
C20···H293^v	3.277	H282···H7^ii	3.576
C20···H301^viii	3.159	H282···H111^ii	2.719
C20···H303^viii	3.407	H283···O1^i	2.642
C21···H201^vii	3.323	H283···C1^i	3.329
C21···H203^vii	3.369	H283···C6^iii	3.561
C21···H211^vii	3.382	H283···H2^iii	3.268
C21···H213^vii	3.270	H283···H2^i	3.522
C21···H291^i	3.582	H283···H6^iii	3.031
C21···H292^i	3.440	H283···H193^xvi	3.172
C21···H301^viii	3.166	H291···C20^ix	3.332
C22···H7^ii	3.590	H291···C20^v	3.290
C23···H7^ii	3.346	H291···C21^i	3.582
C23···H111^ii	3.271	H291···H18^i	3.399
C24···H111^ii	2.957	H291···H201^ix	3.475
C25···H18^i	3.476	H291···H201^v	2.841
C25···H111^ii	3.511	H291···H202^ix	3.128
C27···H1^i	3.583	H291···H202^v	2.904
C28···H2^iii	3.127	H291···H203^ix	2.875
C28···H6^iii	3.079	H291···H211^i	3.041
C28···H111^ii	3.315	H291···H212^i	3.296
C28···H192^v	3.358	H292···O5^v	2.990
C29···H18^i	3.164	H292···O6^v	3.448
C29···H192^v	3.229	H292···C19^v	3.425
C29···H201^v	3.091	H292···C20^v	3.243
C29···H202^v	3.133	H292···C21^i	3.440
C29···H211^i	3.387	H292···H18^i	2.976
C29···H212^i	3.388	H292···H122^xvii	2.850
C30···H112^xi	3.053	H292···H191^v	3.548
C30···H191^ii	3.534	H292···H192^v	3.126
C30···H193^ii	3.333	H292···H201^v	3.145
C30···H203^ix	2.686	H292···H202^v	2.766
C30···H211^i	3.564	H292···H211^i	3.215
H1···C6^ii	3.292	H292···H212^i	2.794
H1···C27^i	3.583	H293···O5^v	2.934
H1···H6^ii	2.870	H293···O6^v	3.452
H2···O8^i	3.336	H293···C11^ii	3.241
H2···C28^x	3.127	H293···C15^v	3.043
H2···H14^ii	3.416	H293···C16^v	3.304
H2···H192^xii	3.345	H293···C19^v	3.349
H2···H281^x	2.401	H293···C20^v	3.277
H2···H282^x	3.284	H293···H111^ii	2.909
H2···H283^x	3.268	H293···H113^ii	2.852
H2···H283^i	3.522	H293···H192^v	2.826
H6···O2^ii	3.074	H293···H201^v	2.774
H6···N1^ii	3.050	H293···H202^v	3.220
H6···N2^ii	3.443	H301···O3^xi	3.435
H6···C1^ii	3.370	H301···O6^ix	3.324
H6···C4^ii	3.353	H301···O7^ix	2.617
H6···C28^x	3.079	H301···C20^ix	3.159
H6···H1^ii	2.870	H301···C21^ix	3.166
H6···H191^xii	3.536	H301···H112^xi	3.131
H6···H281^x	3.045	H301···H203^ix	2.345
H6···H282^x	2.654	H301···H211^i	3.133
H6···H283^x	3.031	H301···H212^ix	3.557
H7···C22^ii	3.590	H301···H213^ix	2.801
H7···C23^ii	3.346	H302···O3^xi	3.268
H7···H23^ii	3.261	H302···C7^xi	3.453
H7···H282^x	3.586	H302···C8^xi	3.357
H7···H282^ii	3.576	H302···C11^xi	3.261
H7···H302^xi	3.353	H302···C19^ii	3.277
H10···H191^xii	3.454	H302···H7^xi	3.353
H14···O1^ii	2.459	H302···H112^xi	2.508
H14···C1^ii	3.420	H302···H191^ii	2.949
H14···H2^ii	3.416	H302···H193^ii	2.855
H14···H27^ii	3.457	H303···O5^ii	3.370
H14···H281^v	2.890	H303···O6^ix	3.539
H18···O9^i	2.501	H303···C19^ii	3.420
H18···O10^i	3.129	H303···C20^ix	3.407
H18···C25^i	3.476	H303···H191^ii	3.453
H18···C29^i	3.164	H303···H193^ii	2.946
H18···H112^iii	3.531	H303···H203^ix	2.686
C8—O3—C11	117.17 (19)	C22—N1—H1	115.7
C9—O4—C12	118.9 (2)	N2—C2—H2	125.4
C15—O5—C19	118.5 (2)	C3—C2—H2	125.3
C16—O6—C20	116.0 (2)	C5—C6—H6	119.1
C17—O7—C21	117.61 (18)	C7—C6—H6	119.2
C24—O8—C28	118.10 (19)	C6—C7—H7	119.7
C25—O9—C29	113.9 (2)	C8—C7—H7	119.5
C26—O10—C30	117.6 (2)	C5—C10—H10	119.2
C1—N1—C22	128.45 (16)	C9—C10—H10	119.1
C1—N2—C2	122.81 (16)	O3—C11—H111	109.5
C1—N2—C4	128.11 (16)	O3—C11—H112	109.4
C2—N2—C4	108.97 (17)	O3—C11—H113	109.5
C3—N3—C4	110.86 (16)	H111—C11—H112	109.5
C3—N3—C13	127.65 (17)	H111—C11—H113	109.5
C4—N3—C13	121.27 (14)	H112—C11—H113	109.5
O1—C1—N1	127.7 (2)	O4—C12—H121	107.3
O1—C1—N2	119.14 (17)	O4—C12—H122	110.7
N1—C1—N2	113.15 (16)	O4—C12—H123	110.4
N2—C2—C3	109.26 (16)	H121—C12—H122	109.5
N3—C3—C2	105.86 (17)	H121—C12—H123	109.5
N3—C3—C5	126.48 (17)	H122—C12—H123	109.4
C2—C3—C5	127.65 (16)	C13—C14—H14	121.0
O2—C4—N2	126.8 (2)	C15—C14—H14	121.0
O2—C4—N3	128.10 (18)	C13—C18—H18	120.6
N2—C4—N3	105.05 (15)	C17—C18—H18	120.6
C3—C5—C6	119.01 (17)	O5—C19—H191	110.0
C3—C5—C10	123.66 (15)	O5—C19—H192	109.2
C6—C5—C10	117.29 (19)	O5—C19—H193	109.1
C5—C6—C7	121.61 (19)	H191—C19—H192	109.5
C6—C7—C8	120.81 (17)	H191—C19—H193	109.5
O3—C8—C7	125.51 (17)	H192—C19—H193	109.5
O3—C8—C9	116.0 (2)	O6—C20—H201	109.0
C7—C8—C9	118.5 (2)	O6—C20—H202	109.8
O4—C9—C8	117.4 (2)	O6—C20—H203	109.7
O4—C9—C10	122.46 (18)	H201—C20—H202	109.5
C8—C9—C10	120.1 (2)	H201—C20—H203	109.5
C5—C10—C9	121.64 (17)	H202—C20—H203	109.4
N3—C13—C14	119.39 (18)	O7—C21—H211	109.3
N3—C13—C18	117.6 (2)	O7—C21—H212	109.4
C14—C13—C18	122.99 (18)	O7—C21—H213	109.7
C13—C14—C15	118.0 (2)	H211—C21—H212	109.5
O5—C15—C14	123.7 (2)	H211—C21—H213	109.5
O5—C15—C16	115.9 (2)	H212—C21—H213	109.5
C14—C15—C16	120.4 (2)	C22—C23—H23	119.8
O6—C16—C15	119.8 (2)	C24—C23—H23	119.9
O6—C16—C17	120.6 (2)	C22—C27—H27	120.7
C15—C16—C17	119.6 (2)	C26—C27—H27	121.0
O7—C17—C16	115.70 (19)	O8—C28—H281	109.4
O7—C17—C18	124.1 (2)	O8—C28—H282	109.1
C16—C17—C18	120.2 (2)	O8—C28—H283	109.9
C13—C18—C17	118.7 (2)	H281—C28—H282	109.5
N1—C22—C23	117.07 (17)	H281—C28—H283	109.5
N1—C22—C27	122.24 (17)	H282—C28—H283	109.5
C23—C22—C27	120.7 (2)	O9—C29—H291	109.8
C22—C23—C24	120.30 (18)	O9—C29—H292	109.5
O8—C24—C23	124.95 (18)	O9—C29—H293	109.1
O8—C24—C25	115.1 (2)	H291—C29—H292	109.5
C23—C24—C25	119.94 (18)	H291—C29—H293	109.5
O9—C25—C24	119.85 (17)	H292—C29—H293	109.5
O9—C25—C26	120.99 (19)	O10—C30—H301	109.6
C24—C25—C26	119.1 (2)	O10—C30—H302	109.5
O10—C26—C25	115.3 (2)	O10—C30—H303	109.3
O10—C26—C27	123.03 (17)	H301—C30—H302	109.5
C25—C26—C27	121.62 (19)	H301—C30—H303	109.5
C22—C27—C26	118.26 (18)	H302—C30—H303	109.5
C1—N1—H1	115.9
C11—O3—C8—C7	−2.5 (4)	C2—C3—C5—C10	149.1 (2)
C11—O3—C8—C9	176.0 (2)	C3—C5—C6—C7	176.0 (2)
C12—O4—C9—C8	179.7 (3)	C3—C5—C10—C9	−176.9 (2)
C12—O4—C9—C10	0.1 (3)	C6—C5—C10—C9	0.6 (4)
C19—O5—C15—C14	−12.8 (3)	C10—C5—C6—C7	−1.7 (4)
C19—O5—C15—C16	168.9 (2)	C5—C6—C7—C8	1.0 (4)
C20—O6—C16—C15	−116.8 (3)	C6—C7—C8—O3	179.1 (2)
C20—O6—C16—C17	64.5 (3)	C6—C7—C8—C9	0.7 (4)
C21—O7—C17—C16	171.8 (2)	O3—C8—C9—O4	0.2 (4)
C21—O7—C17—C18	−8.6 (3)	O3—C8—C9—C10	179.7 (2)
C28—O8—C24—C23	−3.6 (4)	C7—C8—C9—O4	178.8 (2)
C28—O8—C24—C25	177.4 (2)	C7—C8—C9—C10	−1.7 (4)
C29—O9—C25—C24	−88.7 (2)	O4—C9—C10—C5	−179.5 (2)
C29—O9—C25—C26	92.0 (3)	C8—C9—C10—C5	1.0 (4)
C30—O10—C26—C25	−177.5 (2)	N3—C13—C14—C15	179.18 (18)
C30—O10—C26—C27	3.6 (4)	N3—C13—C18—C17	−177.22 (18)
C1—N1—C22—C23	−175.5 (2)	C14—C13—C18—C17	1.9 (3)
C1—N1—C22—C27	3.1 (4)	C18—C13—C14—C15	0.1 (2)
C22—N1—C1—O1	1.4 (4)	C13—C14—C15—O5	−179.1 (2)
C22—N1—C1—N2	−178.4 (2)	C13—C14—C15—C16	−1.0 (3)
C1—N2—C2—C3	177.0 (2)	O5—C15—C16—O6	−0.6 (3)
C2—N2—C1—O1	5.9 (3)	O5—C15—C16—C17	178.2 (2)
C2—N2—C1—N1	−174.3 (2)	C14—C15—C16—O6	−178.9 (2)
C1—N2—C4—O2	4.1 (4)	C14—C15—C16—C17	−0.1 (3)
C1—N2—C4—N3	−176.7 (2)	O6—C16—C17—O7	0.5 (3)
C4—N2—C1—O1	−178.4 (2)	O6—C16—C17—C18	−179.14 (19)
C4—N2—C1—N1	1.4 (3)	C15—C16—C17—O7	−178.2 (2)
C2—N2—C4—O2	−179.7 (2)	C15—C16—C17—C18	2.1 (3)
C2—N2—C4—N3	−0.5 (2)	O7—C17—C18—C13	177.42 (19)
C4—N2—C2—C3	0.6 (2)	C16—C17—C18—C13	−3.0 (3)
C3—N3—C4—O2	179.4 (2)	N1—C22—C23—C24	179.4 (2)
C3—N3—C4—N2	0.2 (2)	N1—C22—C27—C26	−179.7 (2)
C4—N3—C3—C2	0.2 (2)	C23—C22—C27—C26	−1.1 (4)
C4—N3—C3—C5	179.1 (2)	C27—C22—C23—C24	0.7 (4)
C3—N3—C13—C14	−87.0 (2)	C22—C23—C24—O8	179.7 (2)
C3—N3—C13—C18	92.1 (2)	C22—C23—C24—C25	−1.3 (4)
C13—N3—C3—C2	−174.4 (2)	O8—C24—C25—O9	2.0 (3)
C13—N3—C3—C5	4.5 (3)	O8—C24—C25—C26	−178.7 (2)
C4—N3—C13—C14	98.9 (2)	C23—C24—C25—O9	−177.1 (2)
C4—N3—C13—C18	−82.0 (2)	C23—C24—C25—C26	2.2 (4)
C13—N3—C4—O2	−5.5 (4)	O9—C25—C26—O10	−2.3 (3)
C13—N3—C4—N2	175.2 (2)	O9—C25—C26—C27	176.6 (2)
N2—C2—C3—N3	−0.5 (2)	C24—C25—C26—O10	178.4 (2)
N2—C2—C3—C5	−179.4 (2)	C24—C25—C26—C27	−2.7 (4)
N3—C3—C5—C6	152.9 (2)	O10—C26—C27—C22	−179.1 (2)
N3—C3—C5—C10	−29.6 (4)	C25—C26—C27—C22	2.1 (4)
C2—C3—C5—C6	−28.4 (4)

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x−1, y−1, z; (iv) −x+2, −y+1, −z; (v) −x+1, −y, −z+1; (vi) −x+1, −y+1, −z; (vii) −x+1, −y, −z; (viii) x−1, y, z−1; (ix) x+1, y, z+1; (x) x+1, y+1, z; (xi) −x+3, −y+1, −z+1; (xii) x+1, y, z; (xiii) x, y+1, z−1; (xiv) x−1, y, z; (xv) x, y+1, z; (xvi) x, y−1, z; (xvii) x, y−1, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.97	2.698 (2)	142