Ethyl 2-{[(1Z)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl-idene)(p-tol-yl)meth-yl]amino}-3-phenyl-propanoate.

The asymmetric unit of the title compound, C(29)H(29)N(3)O(3), contains two mol-ecules, which exist in their enamine-keto form, being stabilized by strong intra-molecular N-H⋯O hydrogen bonds, which generate S(6) loops. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains, which are further linked by weak C-H⋯π inter-actions, forming a two-dimensional network.

Related literature

For general background to Schiff base compounds in coordination chemistry, see: Habibi et al. (2007 ▶). For the anti­bacterial properties of Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes, see: Li et al. (1997 ▶, 2004 ▶). For the anti­bacterial and biological activity of amino acid esters, see: Xiong et al. (1993 ▶). For related structures, see: Wang et al. (2003 ▶); Zhang et al. (2004 ▶). For further synthetic details, see: Remya et al. (2005 ▶).

Experimental

Crystal data

C29H29N3O3

M = 467.55

Triclinic,

a = 11.0637 (11) Å

b = 13.2746 (14) Å

c = 20.299 (2) Å

α = 101.869 (2)°

β = 97.923 (2)°

γ = 112.861 (2)°

V = 2608.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.38 × 0.32 × 0.26 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.971, T max = 0.980

13503 measured reflections

9153 independent reflections

5450 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.132

S = 1.01

9153 reflections

636 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054865/hb5268sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054865/hb5268Isup2.hkl

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

C29H29N3O3	Z = 4
Mr = 467.55	F(000) = 992
Triclinic, P1	Dx = 1.190 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.0637 (11) Å	Cell parameters from 2516 reflections
b = 13.2746 (14) Å	θ = 2.3–20.2°
c = 20.299 (2) Å	µ = 0.08 mm−1
α = 101.869 (2)°	T = 296 K
β = 97.923 (2)°	Block, yellow
γ = 112.861 (2)°	0.38 × 0.32 × 0.26 mm
V = 2608.8 (5) Å3

Bruker SMART CCD diffractometer	9153 independent reflections
Radiation source: fine-focus sealed tube	5450 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −13→11
Tmin = 0.971, Tmax = 0.980	k = −10→15
13503 measured reflections	l = −24→23

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.1678P] where P = (Fo2 + 2Fc2)/3
9153 reflections	(Δ/σ)max = 0.001
636 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 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
O1	0.71923 (17)	0.81845 (14)	0.49334 (9)	0.0766 (5)
O2	0.3638 (2)	0.8629 (2)	0.49767 (10)	0.1062 (7)
O3	0.29842 (17)	0.92431 (15)	0.59120 (9)	0.0799 (5)
O4	0.24307 (14)	0.80519 (12)	1.00473 (7)	0.0631 (4)
O5	−0.08684 (17)	0.87650 (15)	1.01365 (8)	0.0776 (5)
O6	−0.25145 (15)	0.84962 (13)	0.92501 (7)	0.0649 (4)
N1	0.77524 (18)	0.66606 (16)	0.49565 (9)	0.0609 (5)
N2	0.74399 (19)	0.57817 (16)	0.52761 (9)	0.0616 (5)
N3	0.55387 (18)	0.82573 (16)	0.57946 (9)	0.0617 (5)
H3A	0.5857	0.8429	0.5449	0.074*
N4	0.29698 (16)	0.65042 (14)	0.99683 (9)	0.0513 (4)
N5	0.23374 (18)	0.53247 (14)	0.96488 (9)	0.0547 (5)
N6	−0.01134 (18)	0.73294 (15)	0.92980 (9)	0.0598 (5)
H6	0.0499	0.7785	0.9666	0.072*
C1	0.9533 (3)	0.6259 (2)	0.45793 (15)	0.0834 (8)
H1	0.9543	0.5868	0.4910	0.100*
C2	1.0407 (3)	0.6352 (3)	0.4136 (2)	0.1111 (11)
H2	1.1001	0.6016	0.4171	0.133*
C3	1.0397 (4)	0.6932 (3)	0.3653 (2)	0.1202 (13)
H3	1.0988	0.6993	0.3364	0.144*
C4	0.9522 (3)	0.7420 (3)	0.35953 (17)	0.1045 (10)
H4	0.9515	0.7809	0.3263	0.125*
C5	0.8643 (3)	0.7342 (2)	0.40263 (14)	0.0801 (8)
H5	0.8050	0.7679	0.3987	0.096*
C6	0.8655 (2)	0.6759 (2)	0.45169 (13)	0.0667 (7)
C7	0.7118 (2)	0.7346 (2)	0.51423 (11)	0.0591 (6)
C8	0.6389 (2)	0.68835 (18)	0.56273 (10)	0.0520 (5)
C9	0.6635 (2)	0.59172 (19)	0.56667 (11)	0.0551 (6)
C10	0.6086 (3)	0.5064 (2)	0.60524 (12)	0.0732 (7)
H10A	0.6391	0.4479	0.5940	0.110*
H10B	0.5116	0.4729	0.5923	0.110*
H10C	0.6397	0.5435	0.6542	0.110*
C11	0.5662 (2)	0.73839 (18)	0.59647 (10)	0.0508 (5)
C12	0.5048 (2)	0.69619 (18)	0.65205 (10)	0.0497 (5)
C13	0.3756 (2)	0.6121 (2)	0.63623 (11)	0.0634 (6)
H13	0.3223	0.5857	0.5912	0.076*
C14	0.3246 (3)	0.5665 (2)	0.68735 (12)	0.0720 (7)
H14	0.2368	0.5095	0.6760	0.086*
C15	0.3998 (3)	0.6030 (2)	0.75424 (12)	0.0689 (7)
C16	0.5282 (3)	0.6890 (2)	0.76938 (12)	0.0757 (7)
H16	0.5810	0.7159	0.8145	0.091*
C17	0.5807 (2)	0.7364 (2)	0.71958 (11)	0.0648 (6)
H17	0.6672	0.7954	0.7315	0.078*
C18	0.3415 (3)	0.5521 (3)	0.80965 (15)	0.1137 (11)
H18A	0.2749	0.5776	0.8210	0.170*
H18B	0.4126	0.5760	0.8504	0.170*
H18C	0.3003	0.4704	0.7925	0.170*
C19	0.4935 (2)	0.89585 (19)	0.61186 (11)	0.0596 (6)
H19	0.4596	0.8685	0.6500	0.071*
C20	0.5985 (2)	1.0210 (2)	0.64057 (12)	0.0695 (7)
H20A	0.6400	1.0446	0.6039	0.083*
H20B	0.5525	1.0681	0.6543	0.083*
C21	0.7078 (2)	1.04170 (19)	0.70174 (12)	0.0595 (6)
C22	0.8205 (2)	1.0246 (2)	0.69331 (13)	0.0709 (7)
H22	0.8304	0.9999	0.6489	0.085*
C23	0.9190 (3)	1.0439 (2)	0.75043 (16)	0.0812 (8)
H23	0.9946	1.0320	0.7443	0.097*
C24	0.9055 (3)	1.0806 (2)	0.81618 (15)	0.0781 (8)
H24	0.9723	1.0943	0.8545	0.094*
C25	0.7943 (3)	1.0970 (2)	0.82516 (14)	0.0806 (8)
H25	0.7846	1.1215	0.8696	0.097*
C26	0.6963 (3)	1.0772 (2)	0.76821 (13)	0.0758 (7)
H26	0.6202	1.0880	0.7748	0.091*
C27	0.3774 (3)	0.8892 (2)	0.55943 (14)	0.0695 (7)
C28	0.1891 (3)	0.9351 (3)	0.54875 (16)	0.0943 (9)
H28A	0.1342	0.8644	0.5125	0.113*
H28B	0.2257	0.9955	0.5271	0.113*
C29	0.1067 (3)	0.9618 (3)	0.59471 (19)	0.1302 (13)
H29A	0.0646	0.8986	0.6126	0.195*
H29B	0.0384	0.9759	0.5690	0.195*
H29C	0.1636	1.0284	0.6325	0.195*
C30	0.4752 (2)	0.7986 (2)	1.09284 (12)	0.0640 (6)
H30	0.4203	0.8358	1.1002	0.077*
C31	0.6034 (3)	0.8419 (2)	1.13540 (14)	0.0793 (7)
H31	0.6349	0.9087	1.1714	0.095*
C32	0.6846 (3)	0.7867 (3)	1.12470 (16)	0.0868 (8)
H32	0.7700	0.8153	1.1541	0.104*
C33	0.6400 (3)	0.6900 (3)	1.07104 (16)	0.0837 (8)
H33	0.6958	0.6537	1.0633	0.100*
C34	0.5129 (2)	0.6461 (2)	1.02831 (13)	0.0667 (6)
H34	0.4828	0.5801	0.9918	0.080*
C35	0.4297 (2)	0.70014 (18)	1.03960 (11)	0.0527 (5)
C36	0.2138 (2)	0.70135 (18)	0.98212 (10)	0.0486 (5)
C37	0.0921 (2)	0.61086 (17)	0.93655 (10)	0.0472 (5)
C38	0.1131 (2)	0.50964 (17)	0.92975 (10)	0.0503 (5)
C39	0.0195 (2)	0.38911 (18)	0.89275 (12)	0.0700 (7)
H39A	0.0112	0.3770	0.8437	0.105*
H39B	−0.0676	0.3725	0.9024	0.105*
H39C	0.0544	0.3399	0.9082	0.105*
C40	−0.0169 (2)	0.62915 (18)	0.90837 (10)	0.0486 (5)
C41	−0.1392 (2)	0.54022 (17)	0.85620 (10)	0.0490 (5)
C42	−0.1335 (2)	0.4956 (2)	0.78968 (11)	0.0642 (6)
H42	−0.0510	0.5193	0.7775	0.077*
C43	−0.2494 (3)	0.4158 (2)	0.74106 (12)	0.0730 (7)
H43	−0.2436	0.3865	0.6965	0.088*
C44	−0.3731 (3)	0.3787 (2)	0.75699 (13)	0.0706 (7)
C45	−0.3777 (2)	0.4225 (2)	0.82360 (14)	0.0722 (7)
H45	−0.4601	0.3975	0.8358	0.087*
C46	−0.2635 (2)	0.5025 (2)	0.87262 (12)	0.0620 (6)
H46	−0.2698	0.5314	0.9171	0.074*
C47	−0.5008 (3)	0.2919 (2)	0.70330 (15)	0.1088 (11)
H47A	−0.4778	0.2659	0.6612	0.163*
H47B	−0.5607	0.3265	0.6942	0.163*
H47C	−0.5448	0.2283	0.7206	0.163*
C48	−0.0969 (2)	0.77755 (18)	0.89797 (11)	0.0546 (6)
H48	−0.1760	0.7146	0.8644	0.065*
C49	−0.0201 (2)	0.86357 (19)	0.86083 (12)	0.0654 (6)
H49A	−0.0807	0.8914	0.8401	0.078*
H49B	0.0539	0.9282	0.8950	0.078*
C50	0.0360 (2)	0.81547 (19)	0.80509 (12)	0.0611 (6)
C51	0.1668 (3)	0.8278 (2)	0.81830 (15)	0.0867 (8)
H51	0.2226	0.8663	0.8626	0.104*
C52	0.2163 (3)	0.7838 (3)	0.76661 (19)	0.1075 (10)
H52	0.3050	0.7924	0.7764	0.129*
C53	0.1357 (4)	0.7275 (3)	0.70104 (17)	0.1027 (10)
H53	0.1699	0.6993	0.6660	0.123*
C54	0.0062 (3)	0.7131 (3)	0.68762 (14)	0.0938 (9)
H54	−0.0496	0.6736	0.6434	0.113*
C55	−0.0432 (3)	0.7568 (2)	0.73906 (13)	0.0792 (7)
H55	−0.1326	0.7464	0.7290	0.095*
C56	−0.1432 (2)	0.83904 (18)	0.95348 (12)	0.0559 (6)
C57	−0.3000 (2)	0.9187 (2)	0.96945 (12)	0.0712 (7)
H57A	−0.2362	0.9984	0.9827	0.085*
H57B	−0.3104	0.8949	1.0112	0.085*
C58	−0.4329 (3)	0.9022 (2)	0.92927 (14)	0.0898 (8)
H58A	−0.4228	0.9202	0.8863	0.135*
H58B	−0.4643	0.9516	0.9558	0.135*
H58C	−0.4973	0.8244	0.9199	0.135*

	U11	U22	U33	U12	U13	U23
O1	0.0967 (13)	0.0666 (11)	0.0890 (12)	0.0408 (10)	0.0529 (10)	0.0364 (10)
O2	0.1053 (15)	0.157 (2)	0.0633 (12)	0.0714 (15)	0.0118 (11)	0.0198 (13)
O3	0.0790 (12)	0.0933 (13)	0.0854 (12)	0.0542 (11)	0.0211 (10)	0.0268 (10)
O4	0.0664 (10)	0.0462 (9)	0.0731 (10)	0.0302 (8)	0.0019 (8)	0.0076 (8)
O5	0.0844 (12)	0.0958 (13)	0.0531 (10)	0.0533 (11)	0.0010 (9)	0.0034 (9)
O6	0.0677 (10)	0.0708 (11)	0.0603 (9)	0.0456 (9)	0.0032 (8)	0.0033 (8)
N1	0.0631 (12)	0.0593 (12)	0.0646 (12)	0.0269 (10)	0.0288 (10)	0.0165 (10)
N2	0.0683 (12)	0.0587 (12)	0.0589 (11)	0.0290 (10)	0.0182 (10)	0.0138 (10)
N3	0.0771 (13)	0.0679 (13)	0.0563 (11)	0.0393 (11)	0.0305 (10)	0.0248 (10)
N4	0.0500 (11)	0.0447 (11)	0.0613 (11)	0.0261 (9)	0.0077 (9)	0.0117 (9)
N5	0.0607 (12)	0.0452 (11)	0.0615 (11)	0.0280 (9)	0.0113 (10)	0.0136 (9)
N6	0.0675 (12)	0.0537 (12)	0.0559 (11)	0.0363 (10)	−0.0058 (9)	0.0042 (9)
C1	0.0691 (17)	0.0748 (18)	0.099 (2)	0.0304 (15)	0.0289 (16)	0.0060 (15)
C2	0.083 (2)	0.091 (2)	0.155 (3)	0.0365 (19)	0.059 (2)	0.008 (2)
C3	0.110 (3)	0.091 (3)	0.157 (3)	0.028 (2)	0.092 (3)	0.021 (2)
C4	0.120 (3)	0.084 (2)	0.118 (2)	0.035 (2)	0.078 (2)	0.0294 (19)
C5	0.0825 (19)	0.0724 (18)	0.0863 (18)	0.0255 (15)	0.0465 (16)	0.0224 (15)
C6	0.0580 (15)	0.0572 (15)	0.0730 (16)	0.0168 (12)	0.0272 (13)	0.0028 (13)
C7	0.0584 (14)	0.0550 (15)	0.0615 (14)	0.0218 (12)	0.0206 (12)	0.0124 (12)
C8	0.0537 (13)	0.0542 (13)	0.0488 (12)	0.0230 (11)	0.0177 (10)	0.0131 (11)
C9	0.0577 (14)	0.0597 (15)	0.0465 (12)	0.0260 (12)	0.0109 (11)	0.0118 (11)
C10	0.0963 (19)	0.0688 (17)	0.0644 (15)	0.0409 (15)	0.0259 (14)	0.0242 (13)
C11	0.0477 (12)	0.0528 (14)	0.0436 (12)	0.0165 (11)	0.0078 (10)	0.0088 (10)
C12	0.0508 (13)	0.0546 (13)	0.0423 (12)	0.0233 (11)	0.0123 (10)	0.0088 (10)
C13	0.0614 (15)	0.0665 (16)	0.0465 (13)	0.0158 (13)	0.0101 (11)	0.0093 (12)
C14	0.0735 (16)	0.0625 (16)	0.0628 (16)	0.0111 (13)	0.0263 (14)	0.0123 (13)
C15	0.0896 (19)	0.0717 (17)	0.0528 (15)	0.0370 (16)	0.0308 (14)	0.0194 (13)
C16	0.0830 (19)	0.104 (2)	0.0425 (13)	0.0455 (18)	0.0106 (13)	0.0170 (14)
C17	0.0558 (14)	0.0799 (17)	0.0482 (14)	0.0245 (13)	0.0083 (11)	0.0087 (13)
C18	0.155 (3)	0.123 (3)	0.088 (2)	0.060 (2)	0.066 (2)	0.056 (2)
C19	0.0682 (15)	0.0646 (15)	0.0545 (13)	0.0357 (13)	0.0191 (12)	0.0175 (12)
C20	0.0818 (17)	0.0656 (16)	0.0653 (15)	0.0384 (14)	0.0125 (13)	0.0174 (13)
C21	0.0676 (15)	0.0531 (14)	0.0584 (15)	0.0268 (12)	0.0148 (12)	0.0157 (11)
C22	0.0697 (17)	0.0745 (17)	0.0682 (16)	0.0282 (14)	0.0213 (14)	0.0224 (13)
C23	0.0619 (17)	0.0771 (19)	0.103 (2)	0.0280 (15)	0.0158 (16)	0.0279 (17)
C24	0.082 (2)	0.0573 (16)	0.0770 (19)	0.0183 (14)	−0.0039 (15)	0.0207 (14)
C25	0.094 (2)	0.0754 (19)	0.0606 (16)	0.0312 (17)	0.0121 (16)	0.0096 (14)
C26	0.0777 (17)	0.0802 (19)	0.0651 (17)	0.0374 (15)	0.0150 (14)	0.0062 (14)
C27	0.0703 (17)	0.0749 (18)	0.0681 (18)	0.0339 (15)	0.0199 (14)	0.0227 (14)
C28	0.0720 (18)	0.093 (2)	0.121 (2)	0.0429 (17)	0.0049 (18)	0.0337 (19)
C29	0.110 (3)	0.145 (3)	0.185 (4)	0.088 (3)	0.056 (3)	0.069 (3)
C30	0.0568 (15)	0.0622 (16)	0.0718 (16)	0.0288 (13)	0.0098 (13)	0.0141 (13)
C31	0.0630 (17)	0.0732 (18)	0.0826 (18)	0.0192 (15)	0.0029 (14)	0.0134 (14)
C32	0.0466 (15)	0.092 (2)	0.109 (2)	0.0200 (16)	0.0009 (15)	0.0339 (19)
C33	0.0530 (16)	0.086 (2)	0.118 (2)	0.0347 (15)	0.0158 (16)	0.0331 (19)
C34	0.0590 (15)	0.0660 (16)	0.0834 (17)	0.0333 (13)	0.0197 (13)	0.0236 (13)
C35	0.0488 (13)	0.0527 (14)	0.0617 (14)	0.0247 (11)	0.0125 (11)	0.0216 (12)
C36	0.0538 (13)	0.0473 (13)	0.0527 (13)	0.0282 (11)	0.0133 (10)	0.0172 (11)
C37	0.0514 (13)	0.0460 (12)	0.0505 (12)	0.0281 (11)	0.0103 (10)	0.0139 (10)
C38	0.0570 (14)	0.0468 (13)	0.0497 (12)	0.0252 (11)	0.0112 (11)	0.0146 (10)
C39	0.0757 (16)	0.0449 (14)	0.0826 (17)	0.0272 (13)	0.0033 (13)	0.0124 (12)
C40	0.0576 (13)	0.0498 (13)	0.0448 (12)	0.0278 (11)	0.0139 (10)	0.0160 (10)
C41	0.0560 (13)	0.0470 (13)	0.0480 (13)	0.0279 (11)	0.0078 (11)	0.0135 (10)
C42	0.0650 (15)	0.0743 (17)	0.0573 (15)	0.0386 (14)	0.0113 (12)	0.0117 (13)
C43	0.0835 (19)	0.0774 (18)	0.0542 (15)	0.0437 (16)	0.0008 (14)	0.0027 (13)
C44	0.0768 (18)	0.0536 (15)	0.0696 (17)	0.0253 (14)	−0.0079 (14)	0.0158 (13)
C45	0.0599 (15)	0.0656 (17)	0.0803 (18)	0.0141 (13)	0.0089 (14)	0.0302 (15)
C46	0.0644 (16)	0.0639 (15)	0.0572 (14)	0.0239 (13)	0.0173 (12)	0.0221 (12)
C47	0.096 (2)	0.082 (2)	0.106 (2)	0.0169 (18)	−0.0275 (18)	0.0158 (18)
C48	0.0609 (14)	0.0509 (13)	0.0538 (13)	0.0333 (12)	0.0023 (11)	0.0075 (11)
C49	0.0808 (17)	0.0587 (15)	0.0656 (15)	0.0418 (14)	0.0127 (13)	0.0156 (12)
C50	0.0661 (16)	0.0585 (15)	0.0641 (15)	0.0339 (13)	0.0132 (13)	0.0162 (12)
C51	0.0710 (18)	0.100 (2)	0.0845 (19)	0.0420 (17)	0.0091 (15)	0.0132 (16)
C52	0.076 (2)	0.141 (3)	0.117 (3)	0.062 (2)	0.029 (2)	0.025 (2)
C53	0.107 (3)	0.136 (3)	0.089 (2)	0.072 (2)	0.042 (2)	0.028 (2)
C54	0.101 (2)	0.116 (3)	0.0665 (18)	0.058 (2)	0.0163 (17)	0.0102 (16)
C55	0.0745 (17)	0.099 (2)	0.0676 (17)	0.0487 (16)	0.0117 (15)	0.0125 (15)
C56	0.0560 (14)	0.0507 (13)	0.0566 (15)	0.0250 (11)	0.0038 (12)	0.0082 (11)
C57	0.0790 (17)	0.0708 (17)	0.0755 (16)	0.0488 (15)	0.0207 (14)	0.0098 (13)
C58	0.0792 (19)	0.098 (2)	0.105 (2)	0.0576 (17)	0.0228 (16)	0.0164 (17)

O1—C7	1.248 (3)	C24—C25	1.358 (4)
O2—C27	1.201 (3)	C24—H24	0.9300
O3—C27	1.320 (3)	C25—C26	1.374 (3)
O3—C28	1.457 (3)	C25—H25	0.9300
O4—C36	1.252 (2)	C26—H26	0.9300
O5—C56	1.195 (2)	C28—C29	1.475 (4)
O6—C56	1.327 (2)	C28—H28A	0.9700
O6—C57	1.456 (2)	C28—H28B	0.9700
N1—C7	1.375 (3)	C29—H29A	0.9600
N1—N2	1.401 (2)	C29—H29B	0.9600
N1—C6	1.415 (3)	C29—H29C	0.9600
N2—C9	1.309 (3)	C30—C35	1.374 (3)
N3—C11	1.325 (3)	C30—C31	1.383 (3)
N3—C19	1.449 (3)	C30—H30	0.9300
N3—H3A	0.8600	C31—C32	1.376 (4)
N4—C36	1.373 (2)	C31—H31	0.9300
N4—N5	1.403 (2)	C32—C33	1.364 (4)
N4—C35	1.416 (3)	C32—H32	0.9300
N5—C38	1.310 (2)	C33—C34	1.374 (3)
N6—C40	1.331 (2)	C33—H33	0.9300
N6—C48	1.445 (2)	C34—C35	1.385 (3)
N6—H6	0.8600	C34—H34	0.9300
C1—C6	1.378 (3)	C36—C37	1.433 (3)
C1—C2	1.396 (4)	C37—C40	1.390 (3)
C1—H1	0.9300	C37—C38	1.433 (3)
C2—C3	1.366 (5)	C38—C39	1.483 (3)
C2—H2	0.9300	C39—H39A	0.9600
C3—C4	1.364 (4)	C39—H39B	0.9600
C3—H3	0.9300	C39—H39C	0.9600
C4—C5	1.383 (3)	C40—C41	1.482 (3)
C4—H4	0.9300	C41—C42	1.379 (3)
C5—C6	1.383 (3)	C41—C46	1.383 (3)
C5—H5	0.9300	C42—C43	1.381 (3)
C7—C8	1.443 (3)	C42—H42	0.9300
C8—C11	1.392 (3)	C43—C44	1.373 (3)
C8—C9	1.426 (3)	C43—H43	0.9300
C9—C10	1.492 (3)	C44—C45	1.374 (3)
C10—H10A	0.9600	C44—C47	1.518 (3)
C10—H10B	0.9600	C45—C46	1.375 (3)
C10—H10C	0.9600	C45—H45	0.9300
C11—C12	1.491 (3)	C46—H46	0.9300
C12—C13	1.371 (3)	C47—H47A	0.9600
C12—C17	1.379 (3)	C47—H47B	0.9600
C13—C14	1.384 (3)	C47—H47C	0.9600
C13—H13	0.9300	C48—C56	1.518 (3)
C14—C15	1.370 (3)	C48—C49	1.540 (3)
C14—H14	0.9300	C48—H48	0.9800
C15—C16	1.375 (3)	C49—C50	1.510 (3)
C15—C18	1.521 (3)	C49—H49A	0.9700
C16—C17	1.377 (3)	C49—H49B	0.9700
C16—H16	0.9300	C50—C51	1.372 (3)
C17—H17	0.9300	C50—C55	1.374 (3)
C18—H18A	0.9599	C51—C52	1.378 (4)
C18—H18B	0.9600	C51—H51	0.9300
C18—H18C	0.9600	C52—C53	1.368 (4)
C19—C27	1.512 (3)	C52—H52	0.9300
C19—C20	1.538 (3)	C53—C54	1.350 (4)
C19—H19	0.9800	C53—H53	0.9300
C20—C21	1.506 (3)	C54—C55	1.371 (3)
C20—H20A	0.9700	C54—H54	0.9300
C20—H20B	0.9700	C55—H55	0.9300
C21—C26	1.375 (3)	C57—C58	1.491 (3)
C21—C22	1.378 (3)	C57—H57A	0.9700
C22—C23	1.382 (3)	C57—H57B	0.9700
C22—H22	0.9300	C58—H58A	0.9600
C23—C24	1.373 (3)	C58—H58B	0.9600
C23—H23	0.9300	C58—H58C	0.9600
C27—O3—C28	118.0 (2)	C29—C28—H28B	110.2
C56—O6—C57	117.64 (17)	H28A—C28—H28B	108.5
C7—N1—N2	111.98 (17)	C28—C29—H29A	109.5
C7—N1—C6	128.7 (2)	C28—C29—H29B	109.5
N2—N1—C6	119.28 (19)	H29A—C29—H29B	109.5
C9—N2—N1	106.36 (17)	C28—C29—H29C	109.5
C11—N3—C19	128.05 (18)	H29A—C29—H29C	109.5
C11—N3—H3A	116.0	H29B—C29—H29C	109.5
C19—N3—H3A	116.0	C35—C30—C31	119.5 (2)
C36—N4—N5	111.77 (16)	C35—C30—H30	120.2
C36—N4—C35	129.02 (18)	C31—C30—H30	120.2
N5—N4—C35	119.18 (16)	C32—C31—C30	120.3 (3)
C38—N5—N4	106.38 (16)	C32—C31—H31	119.9
C40—N6—C48	127.15 (18)	C30—C31—H31	119.9
C40—N6—H6	116.4	C33—C32—C31	120.0 (3)
C48—N6—H6	116.4	C33—C32—H32	120.0
C6—C1—C2	118.7 (3)	C31—C32—H32	120.0
C6—C1—H1	120.7	C32—C33—C34	120.3 (3)
C2—C1—H1	120.7	C32—C33—H33	119.9
C3—C2—C1	120.7 (3)	C34—C33—H33	119.9
C3—C2—H2	119.7	C33—C34—C35	120.0 (2)
C1—C2—H2	119.7	C33—C34—H34	120.0
C4—C3—C2	120.1 (3)	C35—C34—H34	120.0
C4—C3—H3	119.9	C30—C35—C34	119.9 (2)
C2—C3—H3	119.9	C30—C35—N4	121.19 (19)
C3—C4—C5	120.5 (3)	C34—C35—N4	118.9 (2)
C3—C4—H4	119.7	O4—C36—N4	125.45 (19)
C5—C4—H4	119.7	O4—C36—C37	129.52 (18)
C6—C5—C4	119.4 (3)	N4—C36—C37	105.02 (17)
C6—C5—H5	120.3	C40—C37—C38	132.1 (2)
C4—C5—H5	120.3	C40—C37—C36	122.48 (18)
C1—C6—C5	120.6 (2)	C38—C37—C36	105.47 (17)
C1—C6—N1	119.3 (2)	N5—C38—C37	111.32 (19)
C5—C6—N1	120.1 (2)	N5—C38—C39	118.58 (19)
O1—C7—N1	126.4 (2)	C37—C38—C39	130.0 (2)
O1—C7—C8	129.1 (2)	C38—C39—H39A	109.5
N1—C7—C8	104.5 (2)	C38—C39—H39B	109.5
C11—C8—C9	132.3 (2)	H39A—C39—H39B	109.5
C11—C8—C7	122.2 (2)	C38—C39—H39C	109.5
C9—C8—C7	105.55 (18)	H39A—C39—H39C	109.5
N2—C9—C8	111.57 (19)	H39B—C39—H39C	109.5
N2—C9—C10	118.3 (2)	N6—C40—C37	118.00 (19)
C8—C9—C10	130.1 (2)	N6—C40—C41	117.83 (18)
C9—C10—H10A	109.5	C37—C40—C41	124.17 (18)
C9—C10—H10B	109.5	C42—C41—C46	118.2 (2)
H10A—C10—H10B	109.5	C42—C41—C40	121.3 (2)
C9—C10—H10C	109.5	C46—C41—C40	120.46 (19)
H10A—C10—H10C	109.5	C41—C42—C43	120.4 (2)
H10B—C10—H10C	109.5	C41—C42—H42	119.8
N3—C11—C8	119.18 (19)	C43—C42—H42	119.8
N3—C11—C12	120.08 (18)	C44—C43—C42	121.5 (2)
C8—C11—C12	120.7 (2)	C44—C43—H43	119.2
C13—C12—C17	119.0 (2)	C42—C43—H43	119.2
C13—C12—C11	120.66 (18)	C43—C44—C45	117.6 (2)
C17—C12—C11	120.16 (19)	C43—C44—C47	121.5 (3)
C12—C13—C14	119.9 (2)	C45—C44—C47	120.9 (3)
C12—C13—H13	120.0	C44—C45—C46	121.7 (2)
C14—C13—H13	120.0	C44—C45—H45	119.2
C15—C14—C13	121.8 (2)	C46—C45—H45	119.2
C15—C14—H14	119.1	C45—C46—C41	120.5 (2)
C13—C14—H14	119.1	C45—C46—H46	119.8
C14—C15—C16	117.4 (2)	C41—C46—H46	119.8
C14—C15—C18	121.0 (3)	C44—C47—H47A	109.5
C16—C15—C18	121.7 (2)	C44—C47—H47B	109.5
C15—C16—C17	121.9 (2)	H47A—C47—H47B	109.5
C15—C16—H16	119.1	C44—C47—H47C	109.5
C17—C16—H16	119.1	H47A—C47—H47C	109.5
C16—C17—C12	119.9 (2)	H47B—C47—H47C	109.5
C16—C17—H17	120.0	N6—C48—C56	109.45 (17)
C12—C17—H17	120.0	N6—C48—C49	111.18 (18)
C15—C18—H18A	109.5	C56—C48—C49	107.89 (17)
C15—C18—H18B	109.5	N6—C48—H48	109.4
H18A—C18—H18B	109.5	C56—C48—H48	109.4
C15—C18—H18C	109.5	C49—C48—H48	109.4
H18A—C18—H18C	109.5	C50—C49—C48	114.14 (18)
H18B—C18—H18C	109.5	C50—C49—H49A	108.7
N3—C19—C27	110.08 (19)	C48—C49—H49A	108.7
N3—C19—C20	110.38 (19)	C50—C49—H49B	108.7
C27—C19—C20	108.61 (18)	C48—C49—H49B	108.7
N3—C19—H19	109.2	H49A—C49—H49B	107.6
C27—C19—H19	109.2	C51—C50—C55	117.6 (2)
C20—C19—H19	109.2	C51—C50—C49	121.6 (2)
C21—C20—C19	113.60 (19)	C55—C50—C49	120.8 (2)
C21—C20—H20A	108.8	C50—C51—C52	120.7 (3)
C19—C20—H20A	108.8	C50—C51—H51	119.6
C21—C20—H20B	108.8	C52—C51—H51	119.6
C19—C20—H20B	108.8	C53—C52—C51	120.3 (3)
H20A—C20—H20B	107.7	C53—C52—H52	119.8
C26—C21—C22	118.0 (2)	C51—C52—H52	119.8
C26—C21—C20	120.3 (2)	C54—C53—C52	119.5 (3)
C22—C21—C20	121.7 (2)	C54—C53—H53	120.2
C21—C22—C23	120.4 (2)	C52—C53—H53	120.2
C21—C22—H22	119.8	C53—C54—C55	120.2 (3)
C23—C22—H22	119.8	C53—C54—H54	119.9
C24—C23—C22	120.2 (3)	C55—C54—H54	119.9
C24—C23—H23	119.9	C54—C55—C50	121.6 (2)
C22—C23—H23	119.9	C54—C55—H55	119.2
C25—C24—C23	119.9 (3)	C50—C55—H55	119.2
C25—C24—H24	120.0	O5—C56—O6	125.0 (2)
C23—C24—H24	120.0	O5—C56—C48	124.8 (2)
C24—C25—C26	119.7 (3)	O6—C56—C48	110.16 (18)
C24—C25—H25	120.2	O6—C57—C58	107.41 (19)
C26—C25—H25	120.2	O6—C57—H57A	110.2
C25—C26—C21	121.8 (2)	C58—C57—H57A	110.2
C25—C26—H26	119.1	O6—C57—H57B	110.2
C21—C26—H26	119.1	C58—C57—H57B	110.2
O2—C27—O3	124.7 (2)	H57A—C57—H57B	108.5
O2—C27—C19	124.7 (2)	C57—C58—H58A	109.5
O3—C27—C19	110.4 (2)	C57—C58—H58B	109.5
O3—C28—C29	107.6 (2)	H58A—C58—H58B	109.5
O3—C28—H28A	110.2	C57—C58—H58C	109.5
C29—C28—H28A	110.2	H58A—C58—H58C	109.5
O3—C28—H28B	110.2	H58B—C58—H58C	109.5
C7—N1—N2—C9	−0.9 (2)	C20—C19—C27—O3	−77.0 (2)
C6—N1—N2—C9	177.74 (19)	C27—O3—C28—C29	173.4 (2)
C36—N4—N5—C38	0.9 (2)	C35—C30—C31—C32	−0.2 (4)
C35—N4—N5—C38	179.14 (17)	C30—C31—C32—C33	1.4 (4)
C6—C1—C2—C3	0.3 (5)	C31—C32—C33—C34	−1.3 (4)
C1—C2—C3—C4	−0.5 (5)	C32—C33—C34—C35	0.1 (4)
C2—C3—C4—C5	0.5 (5)	C31—C30—C35—C34	−1.0 (3)
C3—C4—C5—C6	−0.3 (5)	C31—C30—C35—N4	177.2 (2)
C2—C1—C6—C5	−0.1 (4)	C33—C34—C35—C30	1.0 (3)
C2—C1—C6—N1	179.3 (2)	C33—C34—C35—N4	−177.2 (2)
C4—C5—C6—C1	0.1 (4)	C36—N4—C35—C30	25.2 (3)
C4—C5—C6—N1	−179.3 (2)	N5—N4—C35—C30	−152.77 (19)
C7—N1—C6—C1	157.5 (2)	C36—N4—C35—C34	−156.7 (2)
N2—N1—C6—C1	−20.9 (3)	N5—N4—C35—C34	25.4 (3)
C7—N1—C6—C5	−23.1 (4)	N5—N4—C36—O4	178.62 (19)
N2—N1—C6—C5	158.5 (2)	C35—N4—C36—O4	0.6 (3)
N2—N1—C7—O1	−179.0 (2)	N5—N4—C36—C37	−1.7 (2)
C6—N1—C7—O1	2.5 (4)	C35—N4—C36—C37	−179.78 (19)
N2—N1—C7—C8	1.7 (2)	O4—C36—C37—C40	1.4 (3)
C6—N1—C7—C8	−176.8 (2)	N4—C36—C37—C40	−178.28 (18)
O1—C7—C8—C11	−2.5 (4)	O4—C36—C37—C38	−178.5 (2)
N1—C7—C8—C11	176.71 (19)	N4—C36—C37—C38	1.9 (2)
O1—C7—C8—C9	179.0 (2)	N4—N5—C38—C37	0.4 (2)
N1—C7—C8—C9	−1.8 (2)	N4—N5—C38—C39	−177.18 (18)
N1—N2—C9—C8	−0.4 (2)	C40—C37—C38—N5	178.7 (2)
N1—N2—C9—C10	177.50 (18)	C36—C37—C38—N5	−1.4 (2)
C11—C8—C9—N2	−176.9 (2)	C40—C37—C38—C39	−4.1 (4)
C7—C8—C9—N2	1.4 (2)	C36—C37—C38—C39	175.8 (2)
C11—C8—C9—C10	5.5 (4)	C48—N6—C40—C37	165.84 (19)
C7—C8—C9—C10	−176.2 (2)	C48—N6—C40—C41	−14.5 (3)
C19—N3—C11—C8	−174.1 (2)	C38—C37—C40—N6	173.7 (2)
C19—N3—C11—C12	4.7 (3)	C36—C37—C40—N6	−6.1 (3)
C9—C8—C11—N3	−176.2 (2)	C38—C37—C40—C41	−6.0 (4)
C7—C8—C11—N3	5.8 (3)	C36—C37—C40—C41	174.20 (18)
C9—C8—C11—C12	5.0 (4)	N6—C40—C41—C42	112.5 (2)
C7—C8—C11—C12	−173.09 (19)	C37—C40—C41—C42	−67.8 (3)
N3—C11—C12—C13	90.7 (3)	N6—C40—C41—C46	−65.4 (3)
C8—C11—C12—C13	−90.5 (3)	C37—C40—C41—C46	114.3 (2)
N3—C11—C12—C17	−93.4 (3)	C46—C41—C42—C43	0.4 (3)
C8—C11—C12—C17	85.4 (3)	C40—C41—C42—C43	−177.6 (2)
C17—C12—C13—C14	−1.9 (3)	C41—C42—C43—C44	0.1 (4)
C11—C12—C13—C14	174.0 (2)	C42—C43—C44—C45	−0.9 (4)
C12—C13—C14—C15	0.0 (4)	C42—C43—C44—C47	179.4 (2)
C13—C14—C15—C16	1.3 (4)	C43—C44—C45—C46	1.3 (4)
C13—C14—C15—C18	179.7 (2)	C47—C44—C45—C46	−179.0 (2)
C14—C15—C16—C17	−0.7 (4)	C44—C45—C46—C41	−0.9 (4)
C18—C15—C16—C17	−179.1 (3)	C42—C41—C46—C45	0.0 (3)
C15—C16—C17—C12	−1.2 (4)	C40—C41—C46—C45	178.0 (2)
C13—C12—C17—C16	2.5 (3)	C40—N6—C48—C56	134.3 (2)
C11—C12—C17—C16	−173.5 (2)	C40—N6—C48—C49	−106.6 (2)
C11—N3—C19—C27	−120.7 (2)	N6—C48—C49—C50	58.3 (2)
C11—N3—C19—C20	119.4 (2)	C56—C48—C49—C50	178.36 (19)
N3—C19—C20—C21	−68.9 (2)	C48—C49—C50—C51	−95.1 (3)
C27—C19—C20—C21	170.4 (2)	C48—C49—C50—C55	84.4 (3)
C19—C20—C21—C26	−94.8 (3)	C55—C50—C51—C52	0.8 (4)
C19—C20—C21—C22	84.4 (3)	C49—C50—C51—C52	−179.7 (3)
C26—C21—C22—C23	−0.6 (4)	C50—C51—C52—C53	0.4 (5)
C20—C21—C22—C23	−179.8 (2)	C51—C52—C53—C54	−1.4 (5)
C21—C22—C23—C24	−0.2 (4)	C52—C53—C54—C55	1.3 (5)
C22—C23—C24—C25	0.6 (4)	C53—C54—C55—C50	−0.2 (5)
C23—C24—C25—C26	−0.3 (4)	C51—C50—C55—C54	−0.9 (4)
C24—C25—C26—C21	−0.5 (4)	C49—C50—C55—C54	179.5 (2)
C22—C21—C26—C25	1.0 (4)	C57—O6—C56—O5	4.4 (3)
C20—C21—C26—C25	−179.9 (2)	C57—O6—C56—C48	−172.72 (19)
C28—O3—C27—O2	−1.8 (4)	N6—C48—C56—O5	21.9 (3)
C28—O3—C27—C19	173.7 (2)	C49—C48—C56—O5	−99.2 (3)
N3—C19—C27—O2	−22.5 (3)	N6—C48—C56—O6	−160.91 (17)
C20—C19—C27—O2	98.5 (3)	C49—C48—C56—O6	78.0 (2)
N3—C19—C27—O3	162.01 (19)	C56—O6—C57—C58	−171.0 (2)

Cg6 is the centroid of C30–C35 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1	0.86	2.01	2.713 (2)	138
N6—H6···O4	0.86	2.03	2.698 (2)	133
C16—H16···O6i	0.93	2.51	3.397 (3)	161
C28—H28B···O1ii	0.97	2.44	3.357 (3)	157
C45—H45···Cg6iii	0.93	2.77	3.449 (3)	130
C57—H57B···Cg6iv	0.96	2.78	3.663 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of C30–C35 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1	0.86	2.01	2.713 (2)	138
N6—H6⋯O4	0.86	2.03	2.698 (2)	133
C16—H16⋯O6i	0.93	2.51	3.397 (3)	161
C28—H28B⋯O1ii	0.97	2.44	3.357 (3)	157
C45—H45⋯Cg6iii	0.93	2.77	3.449 (3)	130
C57—H57B⋯Cg6iv	0.96	2.78	3.663 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .