N'-tert-Butyl-N'-(3,5-dimethyl-benzo-yl)-2,2-dimethyl-4-oxochroman-6-carbo-hydrazide.

In the crystal structure of the title compound, C(25)H(30)N(2)O(4), the steric size of the tert-butyl group causes the 3,5-dimethyl-phenyl ring to adopt a transoid geometry with respect to the N-C(O) bond. The six-membered heterocyclic ring is disordered over two sites, with occupancies of 0.553 (4) and 0.447 (4). Intra-molecular C-H⋯O inter-actions are present. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For general background to dibenzoyl­hydrazines and their derivatives, see: Sawada et al. (2003 ▶). For a related structure, see: Zhao et al. (2005 ▶). For the preparation of the title compound, see: Zhao et al. (2007 ▶); Mao et al. (2008 ▶).

Experimental

Crystal data

C25H30N2O4

M = 422.51

Monoclinic,

a = 14.1260 (12) Å

b = 10.6964 (9) Å

c = 15.4370 (13) Å

β = 96.426 (2)°

V = 2317.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 297 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ▶) T min = 0.976, T max = 0.984

13199 measured reflections

5043 independent reflections

3983 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 1.04

5043 reflections

338 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 global, I. DOI: 10.1107/S1600536809028815/fj2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028815/fj2236Isup2.hkl

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

C25H30N2O4	F(000) = 904
Mr = 422.51	Dx = 1.211 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5293 reflections
a = 14.1260 (12) Å	θ = 2.3–27.9°
b = 10.6964 (9) Å	µ = 0.08 mm−1
c = 15.4370 (13) Å	T = 297 K
β = 96.426 (2)°	Block, colorless
V = 2317.8 (3) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	5043 independent reflections
Radiation source: fine-focus sealed tube	3983 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	h = −18→18
Tmin = 0.976, Tmax = 0.984	k = −13→13
13199 measured reflections	l = −19→11

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) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.3537P] where P = (Fo2 + 2Fc2)/3
5043 reflections	(Δ/σ)max = 0.027
338 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.17 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)
C3	0.66849 (13)	1.10349 (14)	−0.10449 (11)	0.0605 (4)
C4	0.67622 (12)	0.88189 (13)	−0.00473 (10)	0.0514 (4)
C5	0.68639 (11)	0.87969 (14)	−0.09323 (9)	0.0494 (3)
C1	0.6450 (5)	0.9997 (11)	0.0354 (8)	0.065 (2)	0.553 (4)
O1	0.6346 (7)	1.0033 (10)	0.1119 (7)	0.114 (3)	0.553 (4)
C2	0.6193 (3)	1.1038 (3)	−0.0289 (2)	0.0658 (10)	0.553 (4)
H2A	0.5515	1.0993	−0.0475	0.079*	0.553 (4)
H2B	0.6314	1.1830	0.0009	0.079*	0.553 (4)
C6	0.6317 (4)	1.1921 (4)	−0.1762 (3)	0.0794 (12)	0.553 (4)
H6A	0.5657	1.1746	−0.1940	0.119*	0.553 (4)
H6B	0.6676	1.1816	−0.2249	0.119*	0.553 (4)
H6C	0.6382	1.2765	−0.1553	0.119*	0.553 (4)
C7	0.7797 (3)	1.1317 (4)	−0.0800 (3)	0.0873 (13)	0.553 (4)
H7A	0.7875	1.2129	−0.0537	0.131*	0.553 (4)
H7B	0.8112	1.1295	−0.1319	0.131*	0.553 (4)
H7C	0.8069	1.0696	−0.0398	0.131*	0.553 (4)
C1'	0.6818 (6)	1.0036 (14)	0.0428 (10)	0.060 (2)	0.447 (4)
O1'	0.6711 (7)	1.0167 (11)	0.1174 (8)	0.0697 (17)	0.447 (4)
C2'	0.7037 (4)	1.1160 (4)	−0.0090 (3)	0.0685 (13)	0.447 (4)
H2'1	0.7721	1.1291	−0.0027	0.082*	0.447 (4)
H2'2	0.6746	1.1890	0.0143	0.082*	0.447 (4)
C7'	0.5527 (3)	1.0980 (4)	−0.1099 (3)	0.0755 (13)	0.447 (4)
H7'1	0.5340	1.0260	−0.0789	0.113*	0.447 (4)
H7'2	0.5262	1.0926	−0.1698	0.113*	0.447 (4)
H7'3	0.5297	1.1722	−0.0843	0.113*	0.447 (4)
C6'	0.6941 (6)	1.2082 (6)	−0.1583 (4)	0.0936 (19)	0.447 (4)
H6'1	0.6725	1.2850	−0.1350	0.140*	0.447 (4)
H6'2	0.6645	1.1974	−0.2169	0.140*	0.447 (4)
H6'3	0.7620	1.2110	−0.1583	0.140*	0.447 (4)
C8	0.68071 (12)	0.77025 (13)	0.04199 (10)	0.0515 (4)
H8	0.6738	0.7719	0.1012	0.062*
C9	0.69514 (10)	0.65732 (12)	0.00237 (9)	0.0440 (3)
C10	0.70566 (10)	0.65759 (14)	−0.08622 (9)	0.0499 (3)
H10	0.7153	0.5823	−0.1141	0.060*
C11	0.70207 (11)	0.76656 (15)	−0.13332 (10)	0.0544 (4)
H11	0.7102	0.7646	−0.1923	0.065*
C12	0.69536 (10)	0.53436 (12)	0.04860 (10)	0.0468 (3)
C13	0.59930 (11)	0.41391 (14)	0.21344 (11)	0.0538 (4)
C14	0.53721 (13)	0.52843 (17)	0.18794 (15)	0.0753 (5)
H14A	0.5673	0.6019	0.2140	0.113*
H14B	0.4759	0.5178	0.2082	0.113*
H14C	0.5296	0.5373	0.1257	0.113*
C15	0.60593 (14)	0.39710 (18)	0.31198 (13)	0.0715 (5)
H15A	0.6370	0.3193	0.3279	0.107*
H15B	0.5430	0.3967	0.3299	0.107*
H15C	0.6420	0.4647	0.3401	0.107*
C16	0.55686 (12)	0.29932 (16)	0.16431 (14)	0.0702 (5)
H16A	0.5496	0.3161	0.1028	0.105*
H16B	0.4957	0.2808	0.1828	0.105*
H16C	0.5985	0.2291	0.1764	0.105*
C17	0.76979 (10)	0.35224 (11)	0.20322 (9)	0.0419 (3)
C18	0.86257 (9)	0.37282 (12)	0.16645 (9)	0.0426 (3)
C19	0.91465 (10)	0.48329 (13)	0.17253 (10)	0.0475 (3)
H19	0.8915	0.5525	0.2000	0.057*
C20	1.00090 (11)	0.49090 (14)	0.13791 (10)	0.0530 (4)
C21	1.03369 (11)	0.38643 (16)	0.09734 (11)	0.0582 (4)
H21	1.0906	0.3920	0.0725	0.070*
C22	0.98488 (11)	0.27454 (15)	0.09244 (11)	0.0561 (4)
C23	0.89924 (10)	0.26895 (13)	0.12762 (10)	0.0494 (3)
H23	0.8655	0.1942	0.1253	0.059*
C24	1.05961 (13)	0.60902 (17)	0.14489 (14)	0.0745 (5)
H24A	1.0845	0.6224	0.2046	0.112*
H24B	1.0203	0.6786	0.1246	0.112*
H24C	1.1113	0.6011	0.1099	0.112*
C25	1.02483 (16)	0.16056 (19)	0.05138 (16)	0.0862 (6)
H25A	1.0685	0.1864	0.0114	0.129*
H25B	0.9737	0.1137	0.0206	0.129*
H25C	1.0577	0.1092	0.0961	0.129*
N1	0.71169 (8)	0.54096 (10)	0.13664 (8)	0.0442 (3)
H1	0.7207 (11)	0.6105 (16)	0.1645 (11)	0.053*
N2	0.69837 (8)	0.43704 (10)	0.18823 (8)	0.0448 (3)
O2	0.68091 (10)	0.98341 (11)	−0.14408 (8)	0.0697 (4)
O3	0.68252 (10)	0.43588 (10)	0.00964 (8)	0.0680 (3)
O4	0.75822 (7)	0.25569 (9)	0.24413 (7)	0.0527 (3)

	U11	U22	U33	U12	U13	U23
C3	0.0823 (11)	0.0413 (8)	0.0569 (9)	−0.0035 (7)	0.0036 (8)	0.0097 (7)
C4	0.0704 (9)	0.0384 (7)	0.0462 (8)	0.0063 (6)	0.0101 (7)	0.0034 (6)
C5	0.0560 (8)	0.0456 (8)	0.0478 (8)	0.0026 (6)	0.0105 (6)	0.0064 (6)
C1	0.100 (5)	0.040 (2)	0.059 (4)	0.013 (4)	0.027 (5)	0.004 (2)
O1	0.236 (10)	0.046 (3)	0.070 (4)	0.024 (5)	0.064 (6)	0.004 (2)
C2	0.092 (3)	0.0395 (14)	0.069 (2)	0.0125 (15)	0.0221 (18)	0.0105 (13)
C6	0.114 (4)	0.053 (2)	0.070 (2)	0.005 (2)	0.007 (3)	0.0194 (18)
C7	0.080 (2)	0.066 (2)	0.115 (3)	−0.0203 (18)	0.006 (2)	0.008 (2)
C1'	0.088 (6)	0.043 (3)	0.049 (3)	0.014 (5)	0.007 (5)	0.0066 (19)
O1'	0.121 (4)	0.042 (3)	0.045 (2)	0.010 (2)	0.008 (3)	−0.0031 (18)
C2'	0.090 (3)	0.047 (2)	0.066 (2)	−0.0059 (19)	−0.003 (2)	−0.0011 (17)
C7'	0.073 (3)	0.078 (3)	0.074 (3)	0.015 (2)	0.002 (2)	0.008 (2)
C6'	0.138 (6)	0.068 (3)	0.079 (4)	−0.023 (4)	0.030 (4)	0.018 (3)
C8	0.0718 (10)	0.0418 (7)	0.0416 (7)	0.0084 (7)	0.0097 (7)	0.0023 (6)
C9	0.0468 (7)	0.0375 (7)	0.0467 (7)	0.0039 (5)	0.0010 (6)	0.0006 (6)
C10	0.0540 (8)	0.0450 (8)	0.0503 (8)	0.0081 (6)	0.0043 (6)	−0.0066 (6)
C11	0.0645 (9)	0.0576 (9)	0.0427 (8)	0.0072 (7)	0.0129 (7)	0.0002 (7)
C12	0.0518 (8)	0.0355 (7)	0.0519 (8)	0.0041 (6)	0.0012 (6)	−0.0016 (6)
C13	0.0501 (8)	0.0415 (7)	0.0715 (10)	0.0016 (6)	0.0140 (7)	−0.0001 (7)
C14	0.0567 (10)	0.0608 (10)	0.1105 (16)	0.0147 (8)	0.0189 (10)	0.0057 (10)
C15	0.0796 (12)	0.0646 (10)	0.0756 (12)	0.0033 (9)	0.0318 (9)	0.0017 (9)
C16	0.0560 (9)	0.0571 (10)	0.0980 (14)	−0.0107 (8)	0.0109 (9)	−0.0075 (9)
C17	0.0512 (7)	0.0313 (6)	0.0425 (7)	0.0004 (5)	0.0026 (6)	−0.0010 (5)
C18	0.0481 (7)	0.0369 (6)	0.0416 (7)	0.0041 (5)	−0.0002 (5)	0.0023 (5)
C19	0.0535 (8)	0.0378 (7)	0.0508 (8)	0.0004 (6)	0.0034 (6)	−0.0028 (6)
C20	0.0506 (8)	0.0504 (8)	0.0570 (9)	−0.0030 (6)	0.0012 (6)	0.0018 (7)
C21	0.0483 (8)	0.0636 (10)	0.0640 (10)	0.0033 (7)	0.0114 (7)	−0.0005 (8)
C22	0.0562 (9)	0.0530 (9)	0.0592 (9)	0.0098 (7)	0.0069 (7)	−0.0067 (7)
C23	0.0544 (8)	0.0381 (7)	0.0549 (8)	0.0028 (6)	0.0025 (6)	−0.0028 (6)
C24	0.0652 (10)	0.0628 (11)	0.0964 (14)	−0.0170 (8)	0.0124 (10)	−0.0043 (10)
C25	0.0850 (13)	0.0685 (12)	0.1098 (16)	0.0131 (10)	0.0317 (12)	−0.0227 (11)
N1	0.0548 (7)	0.0272 (5)	0.0495 (7)	0.0011 (5)	0.0016 (5)	0.0022 (5)
N2	0.0496 (6)	0.0315 (5)	0.0539 (7)	0.0017 (5)	0.0079 (5)	0.0049 (5)
O2	0.1092 (10)	0.0515 (6)	0.0522 (6)	0.0076 (6)	0.0257 (6)	0.0124 (5)
O3	0.1024 (9)	0.0384 (6)	0.0610 (7)	0.0002 (6)	−0.0009 (6)	−0.0085 (5)
O4	0.0645 (6)	0.0345 (5)	0.0598 (6)	0.0032 (4)	0.0096 (5)	0.0099 (4)

C3—C2	1.423 (4)	C11—H11	0.9300
C3—O2	1.4416 (19)	C12—O3	1.2165 (17)
C3—C6'	1.464 (5)	C12—N1	1.3547 (19)
C3—C6	1.504 (4)	C13—N2	1.5143 (18)
C3—C2'	1.509 (4)	C13—C15	1.524 (3)
C3—C7	1.602 (4)	C13—C16	1.528 (2)
C3—C7'	1.629 (5)	C13—C14	1.532 (2)
C4—C5	1.390 (2)	C14—H14A	0.9600
C4—C8	1.3928 (19)	C14—H14B	0.9600
C4—C1	1.492 (11)	C14—H14C	0.9600
C4—C1'	1.492 (15)	C15—H15A	0.9600
C5—O2	1.3562 (17)	C15—H15B	0.9600
C5—C11	1.388 (2)	C15—H15C	0.9600
C1—O1	1.207 (16)	C16—H16A	0.9600
C1—C2	1.509 (12)	C16—H16B	0.9600
C2—H2A	0.9700	C16—H16C	0.9600
C2—H2B	0.9700	C17—O4	1.2310 (15)
C6—H6A	0.9600	C17—N2	1.3572 (17)
C6—H6B	0.9600	C17—C18	1.5016 (19)
C6—H6C	0.9600	C18—C19	1.3896 (19)
C7—H7A	0.9600	C18—C23	1.3898 (19)
C7—H7B	0.9600	C19—C20	1.387 (2)
C7—H7C	0.9600	C19—H19	0.9300
C1'—O1'	1.186 (19)	C20—C21	1.386 (2)
C1'—C2'	1.495 (15)	C20—C24	1.509 (2)
C2'—H2'1	0.9700	C21—C22	1.379 (2)
C2'—H2'2	0.9700	C21—H21	0.9300
C7'—H7'1	0.9600	C22—C23	1.382 (2)
C7'—H7'2	0.9600	C22—C25	1.512 (2)
C7'—H7'3	0.9600	C23—H23	0.9300
C6'—H6'1	0.9600	C24—H24A	0.9600
C6'—H6'2	0.9600	C24—H24B	0.9600
C6'—H6'3	0.9600	C24—H24C	0.9600
C8—C9	1.3794 (19)	C25—H25A	0.9600
C8—H8	0.9300	C25—H25B	0.9600
C9—C10	1.392 (2)	C25—H25C	0.9600
C9—C12	1.4962 (18)	N1—N2	1.3924 (15)
C10—C11	1.372 (2)	N1—H1	0.862 (17)
C10—H10	0.9300
C2—C3—O2	116.33 (16)	C9—C10—H10	119.3
C2—C3—C6'	129.6 (3)	C10—C11—C5	120.18 (13)
O2—C3—C6'	113.1 (3)	C10—C11—H11	119.9
C2—C3—C6	116.2 (3)	C5—C11—H11	119.9
O2—C3—C6	107.3 (2)	O3—C12—N1	122.71 (13)
C2—C3—C2'	48.4 (2)	O3—C12—C9	122.21 (13)
O2—C3—C2'	116.81 (19)	N1—C12—C9	115.07 (11)
C6'—C3—C2'	114.3 (3)	N2—C13—C15	108.69 (13)
C6—C3—C2'	135.4 (3)	N2—C13—C16	109.02 (12)
C2—C3—C7	111.2 (3)	C15—C13—C16	112.19 (14)
O2—C3—C7	96.03 (19)	N2—C13—C14	108.80 (12)
C6'—C3—C7	72.1 (4)	C15—C13—C14	108.68 (15)
C6—C3—C7	107.7 (3)	C16—C13—C14	109.40 (15)
C2'—C3—C7	62.9 (3)	C13—C14—H14A	109.5
C2—C3—C7'	57.5 (2)	C13—C14—H14B	109.5
O2—C3—C7'	96.6 (2)	H14A—C14—H14B	109.5
C6'—C3—C7'	108.0 (4)	C13—C14—H14C	109.5
C6—C3—C7'	73.9 (3)	H14A—C14—H14C	109.5
C2'—C3—C7'	105.9 (3)	H14B—C14—H14C	109.5
C7—C3—C7'	166.1 (3)	C13—C15—H15A	109.5
C5—C4—C8	119.40 (13)	C13—C15—H15B	109.5
C5—C4—C1	119.3 (5)	H15A—C15—H15B	109.5
C8—C4—C1	120.5 (5)	C13—C15—H15C	109.5
C5—C4—C1'	119.5 (6)	H15A—C15—H15C	109.5
C8—C4—C1'	119.8 (6)	H15B—C15—H15C	109.5
O2—C5—C11	117.17 (13)	C13—C16—H16A	109.5
O2—C5—C4	123.34 (13)	C13—C16—H16B	109.5
C11—C5—C4	119.48 (13)	H16A—C16—H16B	109.5
O1—C1—C4	120.5 (10)	C13—C16—H16C	109.5
O1—C1—C2	125.0 (10)	H16A—C16—H16C	109.5
C4—C1—C2	114.3 (8)	H16B—C16—H16C	109.5
C3—C2—C1	115.7 (4)	O4—C17—N2	120.62 (12)
C3—C2—H2A	108.4	O4—C17—C18	119.25 (12)
C1—C2—H2A	108.4	N2—C17—C18	120.08 (11)
C3—C2—H2B	108.4	C19—C18—C23	119.26 (13)
C1—C2—H2B	108.4	C19—C18—C17	125.24 (12)
H2A—C2—H2B	107.4	C23—C18—C17	115.41 (12)
C3—C6—H6A	109.5	C20—C19—C18	120.35 (13)
C3—C6—H6B	109.5	C20—C19—H19	119.8
C3—C6—H6C	109.5	C18—C19—H19	119.8
C3—C7—H7A	109.5	C21—C20—C19	118.65 (14)
C3—C7—H7B	109.5	C21—C20—C24	119.92 (15)
C3—C7—H7C	109.5	C19—C20—C24	121.42 (14)
O1'—C1'—C4	125.0 (12)	C22—C21—C20	122.29 (14)
O1'—C1'—C2'	118.7 (12)	C22—C21—H21	118.9
C4—C1'—C2'	116.2 (10)	C20—C21—H21	118.9
C1'—C2'—C3	112.6 (6)	C21—C22—C23	118.06 (14)
C1'—C2'—H2'1	109.1	C21—C22—C25	120.98 (15)
C3—C2'—H2'1	109.1	C23—C22—C25	120.94 (15)
C1'—C2'—H2'2	109.1	C22—C23—C18	121.33 (13)
C3—C2'—H2'2	109.1	C22—C23—H23	119.3
H2'1—C2'—H2'2	107.8	C18—C23—H23	119.3
C3—C7'—H7'1	109.5	C20—C24—H24A	109.5
C3—C7'—H7'2	109.5	C20—C24—H24B	109.5
H7'1—C7'—H7'2	109.5	H24A—C24—H24B	109.5
C3—C7'—H7'3	109.5	C20—C24—H24C	109.5
H7'1—C7'—H7'3	109.5	H24A—C24—H24C	109.5
H7'2—C7'—H7'3	109.5	H24B—C24—H24C	109.5
C3—C6'—H6'1	109.5	C22—C25—H25A	109.5
C3—C6'—H6'2	109.5	C22—C25—H25B	109.5
H6'1—C6'—H6'2	109.5	H25A—C25—H25B	109.5
C3—C6'—H6'3	109.5	C22—C25—H25C	109.5
H6'1—C6'—H6'3	109.5	H25A—C25—H25C	109.5
H6'2—C6'—H6'3	109.5	H25B—C25—H25C	109.5
C9—C8—C4	121.44 (13)	C12—N1—N2	120.89 (11)
C9—C8—H8	119.3	C12—N1—H1	123.0 (11)
C4—C8—H8	119.3	N2—N1—H1	115.2 (11)
C8—C9—C10	118.11 (12)	C17—N2—N1	119.06 (11)
C8—C9—C12	123.42 (12)	C17—N2—C13	122.53 (11)
C10—C9—C12	118.41 (12)	N1—N2—C13	117.73 (10)
C11—C10—C9	121.39 (13)	C5—O2—C3	119.03 (12)
C11—C10—H10	119.3
C8—C4—C5—O2	178.51 (15)	C4—C5—C11—C10	1.2 (2)
C1—C4—C5—O2	8.4 (4)	C8—C9—C12—O3	159.80 (15)
C1'—C4—C5—O2	−14.6 (4)	C10—C9—C12—O3	−17.1 (2)
C8—C4—C5—C11	−0.8 (2)	C8—C9—C12—N1	−20.8 (2)
C1—C4—C5—C11	−170.9 (4)	C10—C9—C12—N1	162.30 (13)
C1'—C4—C5—C11	166.0 (4)	O4—C17—C18—C19	−134.18 (14)
C5—C4—C1—O1	179.1 (7)	N2—C17—C18—C19	48.51 (19)
C8—C4—C1—O1	9.2 (9)	O4—C17—C18—C23	42.43 (18)
C1'—C4—C1—O1	−85 (3)	N2—C17—C18—C23	−134.88 (13)
C5—C4—C1—C2	5.0 (7)	C23—C18—C19—C20	1.9 (2)
C8—C4—C1—C2	−164.9 (4)	C17—C18—C19—C20	178.41 (13)
C1'—C4—C1—C2	101 (3)	C18—C19—C20—C21	0.0 (2)
O2—C3—C2—C1	41.7 (5)	C18—C19—C20—C24	−179.00 (15)
C6'—C3—C2—C1	−150.7 (6)	C19—C20—C21—C22	−1.9 (2)
C6—C3—C2—C1	169.6 (5)	C24—C20—C21—C22	177.18 (17)
C2'—C3—C2—C1	−61.8 (5)	C20—C21—C22—C23	1.7 (2)
C7—C3—C2—C1	−66.8 (5)	C20—C21—C22—C25	−177.15 (17)
C7'—C3—C2—C1	122.4 (5)	C21—C22—C23—C18	0.4 (2)
O1—C1—C2—C3	156.6 (8)	C25—C22—C23—C18	179.19 (16)
C4—C1—C2—C3	−29.6 (7)	C19—C18—C23—C22	−2.1 (2)
C5—C4—C1'—O1'	177.5 (8)	C17—C18—C23—C22	−178.97 (13)
C8—C4—C1'—O1'	−15.7 (11)	O3—C12—N1—N2	−11.2 (2)
C1—C4—C1'—O1'	82 (3)	C9—C12—N1—N2	169.32 (11)
C5—C4—C1'—C2'	−3.3 (8)	O4—C17—N2—N1	−175.61 (12)
C8—C4—C1'—C2'	163.5 (4)	C18—C17—N2—N1	1.66 (18)
C1—C4—C1'—C2'	−99 (3)	O4—C17—N2—C13	−5.3 (2)
O1'—C1'—C2'—C3	−151.4 (8)	C18—C17—N2—C13	171.97 (12)
C4—C1'—C2'—C3	29.4 (8)	C12—N1—N2—C17	84.40 (16)
C2—C3—C2'—C1'	61.4 (5)	C12—N1—N2—C13	−86.37 (16)
O2—C3—C2'—C1'	−41.0 (6)	C15—C13—N2—C17	61.36 (17)
C6'—C3—C2'—C1'	−176.2 (6)	C16—C13—N2—C17	−61.21 (18)
C6—C3—C2'—C1'	148.0 (6)	C14—C13—N2—C17	179.54 (14)
C7—C3—C2'—C1'	−123.8 (6)	C15—C13—N2—N1	−128.22 (13)
C7'—C3—C2'—C1'	65.1 (6)	C16—C13—N2—N1	109.21 (14)
C5—C4—C8—C9	0.1 (2)	C14—C13—N2—N1	−10.03 (19)
C1—C4—C8—C9	170.0 (4)	C11—C5—O2—C3	−177.56 (14)
C1'—C4—C8—C9	−166.8 (4)	C4—C5—O2—C3	3.1 (2)
C4—C8—C9—C10	0.3 (2)	C2—C3—O2—C5	−28.9 (3)
C4—C8—C9—C12	−176.65 (14)	C6'—C3—O2—C5	161.4 (4)
C8—C9—C10—C11	0.1 (2)	C6—C3—O2—C5	−160.9 (3)
C12—C9—C10—C11	177.22 (13)	C2'—C3—O2—C5	25.7 (3)
C9—C10—C11—C5	−0.9 (2)	C7—C3—O2—C5	88.4 (2)
O2—C5—C11—C10	−178.14 (14)	C7'—C3—O2—C5	−85.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O4	0.96	2.39	3.007 (2)	121
C15—H15A···O4	0.96	2.36	2.918 (2)	117
C8—H8···O4i	0.93	2.48	3.3214 (18)	151
N1—H1···O4i	0.862 (17)	2.096 (18)	2.9442 (15)	167.8 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16C⋯O4	0.96	2.39	3.007 (2)	121
C15—H15A⋯O4	0.96	2.36	2.918 (2)	117
C8—H8⋯O4i	0.93	2.48	3.3214 (18)	151
N1—H1⋯O4i	0.862 (17)	2.096 (18)	2.9442 (15)	167.8 (15)

Symmetry code: (i) .