N′-[4-(Quinolin-8-yl­oxy)butano­yl]benzohydrazide sesquihydrate

The title compound, C₂₀H₁₉N₃O₃·1.5H₂O, has two organic mol­ecules in the asymmetric unit which differ in conformation. The two independent mol­ecules and three water mol­ecules are linked into layers by O—H...O, O—H...N and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.141
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis{N'-[4-(quinolin-8-yloxy)butanoyl]benzohydrazide} trihydrate

Crystal data

C20H19N3O3·1.5H2O	F(000) = 1592
Mr = 376.40	Dx = 1.301 Mg m^−3
Monoclinic, P21/c	Melting point: 353 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.0667 (11) Å	Cell parameters from 5531 reflections
b = 11.8316 (9) Å	θ = 2.5–26.9°
c = 20.2620 (14) Å	µ = 0.09 mm^−1
β = 93.925 (2)°	T = 293 K
V = 3842.7 (5) Å^3	Block, colourless
Z = 8	0.35 × 0.24 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer	6752 independent reflections
Radiation source: fine-focus sealed tube	4823 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→16
Tmin = 0.968, Tmax = 0.991	k = −14→10
19117 measured reflections	l = −24→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.0008P] where P = (Fo^2 + 2Fc^2)/3
6752 reflections	(Δ/σ)max < 0.001
506 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Experimental. Spectroscopic analysis: IR (KBr, ν cm-1): 3020, 1696, 1632; 1H NMR (CDCl3, δ, p.p.m.): 10.73 (s, 1H), 9.01 (s, 1H), 8.89 (d, 1H, J = 4 Hz), 8.13 (d, 1H, J = 8 Hz), 7.82(t, 2H), 7.48–7.52 (m, 6H), 7.10 (d, 1H, J = 6 Hz), 2.69 (t, 2H), 2.33 (t, 2H)

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.

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

	x	y	z	Uiso*/Ueq
O1	0.28140 (6)	0.24714 (9)	0.32175 (5)	0.0496 (3)
O2	0.55389 (7)	0.20132 (10)	0.44011 (6)	0.0581 (3)
O3	0.62314 (7)	0.50418 (11)	0.48969 (6)	0.0610 (3)
O4	0.69478 (6)	0.74746 (9)	0.39708 (5)	0.0514 (3)
O5	0.42663 (7)	0.67133 (10)	0.26801 (7)	0.0663 (4)
O6	0.32191 (8)	0.90385 (12)	0.25990 (6)	0.0714 (4)
O7	0.41038 (7)	0.46395 (10)	0.32471 (6)	0.0560 (3)
H45	0.3638	0.4455	0.3052	0.091 (7)*
H46	0.4203	0.5287	0.3088	0.102 (8)*
O8	0.59914 (8)	0.14163 (10)	0.61243 (6)	0.0638 (3)
H47	0.5511	0.1123	0.6052	0.090 (8)*
H48	0.6137	0.1276	0.6527	0.100 (8)*
O9	0.44777 (9)	0.04066 (14)	0.58538 (10)	0.1196 (7)
H49	0.3985	0.0616	0.5732	0.124 (10)*
H50	0.4501	−0.0296	0.5771	0.152 (12)*
C32	0.56442 (9)	0.74966 (14)	0.29125 (8)	0.0484 (4)
H32A	0.5671	0.8160	0.3194	0.058*
H32B	0.6048	0.7596	0.2583	0.058*
N1	0.25602 (8)	0.42858 (12)	0.24580 (7)	0.0532 (4)
N2	0.51170 (8)	0.33723 (11)	0.50732 (7)	0.0521 (3)
H41	0.4735	0.3849	0.5179	0.062 (5)*
N3	0.58893 (8)	0.34500 (12)	0.54179 (7)	0.0518 (4)
H42	0.5998	0.2901	0.5696	0.060 (5)*
N4	0.72237 (8)	0.93744 (12)	0.46583 (7)	0.0530 (3)
N5	0.46281 (8)	0.82394 (12)	0.21209 (7)	0.0568 (4)
H43	0.5007	0.8710	0.2005	0.066 (6)*
N6	0.38689 (8)	0.82746 (12)	0.17590 (7)	0.0525 (4)
H44	0.3841	0.7902	0.1388	0.062 (5)*
C1	0.20393 (9)	0.25727 (14)	0.29121 (7)	0.0456 (4)
C2	0.14009 (10)	0.18308 (17)	0.29735 (9)	0.0629 (5)
H2	0.1478	0.1202	0.3246	0.075*
C3	0.06211 (12)	0.2014 (2)	0.26233 (11)	0.0788 (6)
H3	0.0191	0.1501	0.2669	0.095*
C4	0.04874 (11)	0.2921 (2)	0.22230 (10)	0.0735 (6)
H4	−0.0028	0.3020	0.1992	0.088*
C5	0.11313 (10)	0.37166 (16)	0.21554 (8)	0.0552 (4)
C6	0.10404 (12)	0.46932 (18)	0.17544 (9)	0.0670 (5)
H6	0.0536	0.4836	0.1516	0.080*
C7	0.16812 (13)	0.54149 (18)	0.17172 (9)	0.0718 (5)
H7	0.1625	0.6061	0.1456	0.086*
C8	0.24343 (12)	0.51783 (17)	0.20775 (9)	0.0664 (5)
H8	0.2873	0.5683	0.2046	0.080*
C9	0.19149 (9)	0.35467 (14)	0.25013 (7)	0.0459 (4)
C10	0.29812 (10)	0.14998 (14)	0.36294 (8)	0.0521 (4)
H10A	0.2875	0.0814	0.3375	0.062*
H10B	0.2620	0.1503	0.3994	0.062*
C11	0.38798 (10)	0.15362 (13)	0.38916 (8)	0.0511 (4)
H11A	0.4232	0.1553	0.3522	0.061*
H11B	0.4008	0.0851	0.4141	0.061*
C12	0.40814 (9)	0.25477 (14)	0.43301 (8)	0.0487 (4)
H12A	0.3948	0.3231	0.4080	0.058*
H12B	0.3729	0.2528	0.4700	0.058*
C13	0.49763 (9)	0.26047 (13)	0.45944 (7)	0.0434 (4)
C14	0.64076 (9)	0.43001 (13)	0.53063 (7)	0.0445 (4)
C15	0.72259 (9)	0.42936 (13)	0.57062 (7)	0.0447 (4)
C16	0.74702 (10)	0.34492 (15)	0.61488 (9)	0.0602 (5)
H16	0.7110	0.2854	0.6221	0.072*
C17	0.82462 (12)	0.34841 (18)	0.64849 (10)	0.0722 (6)
H17	0.8405	0.2911	0.6781	0.087*
C18	0.87828 (11)	0.4353 (2)	0.63864 (10)	0.0727 (6)
H18	0.9312	0.4360	0.6603	0.087*
C19	0.85352 (12)	0.52158 (19)	0.59653 (11)	0.0775 (6)
H19	0.8890	0.5824	0.5909	0.093*
C20	0.77625 (11)	0.51852 (16)	0.56256 (9)	0.0631 (5)
H20	0.7601	0.5772	0.5339	0.076*
C21	0.77343 (9)	0.76230 (14)	0.42374 (7)	0.0465 (4)
C22	0.83802 (10)	0.68895 (16)	0.41717 (9)	0.0583 (5)
H22	0.8293	0.6233	0.3924	0.070*
C23	0.91745 (11)	0.71174 (19)	0.44755 (10)	0.0701 (5)
H23	0.9606	0.6607	0.4426	0.084*
C24	0.93266 (11)	0.80664 (19)	0.48404 (10)	0.0701 (5)
H24	0.9857	0.8201	0.5037	0.084*
C25	0.86755 (11)	0.88503 (16)	0.49202 (9)	0.0584 (5)
C26	0.87799 (13)	0.98521 (19)	0.52915 (10)	0.0734 (6)
H26	0.9295	1.0019	0.5508	0.088*
C27	0.81307 (14)	1.05747 (19)	0.53345 (10)	0.0771 (6)
H27	0.8195	1.1239	0.5578	0.092*
C28	0.73606 (12)	1.03013 (16)	0.50054 (9)	0.0665 (5)
H28	0.6921	1.0806	0.5035	0.080*
C29	0.78735 (10)	0.86386 (14)	0.46100 (8)	0.0479 (4)
C30	0.67837 (10)	0.64735 (13)	0.35794 (8)	0.0511 (4)
H30A	0.6903	0.5806	0.3847	0.061*
H30B	0.7139	0.6462	0.3211	0.061*
C31	0.58846 (10)	0.64749 (14)	0.33265 (8)	0.0534 (4)
H31A	0.5538	0.6446	0.3700	0.064*
H31B	0.5773	0.5800	0.3064	0.064*
C33	0.47893 (9)	0.74231 (13)	0.25689 (8)	0.0461 (4)
C34	0.31881 (10)	0.86492 (13)	0.20382 (8)	0.0470 (4)
C35	0.23854 (9)	0.86070 (13)	0.16226 (8)	0.0448 (4)
C36	0.23152 (10)	0.82919 (16)	0.09629 (8)	0.0573 (4)
H36	0.2787	0.8060	0.0758	0.069*
C37	0.15535 (11)	0.83198 (18)	0.06082 (9)	0.0675 (5)
H37	0.1514	0.8113	0.0164	0.081*
C38	0.08548 (12)	0.86500 (18)	0.09059 (11)	0.0731 (6)
H38	0.0342	0.8673	0.0664	0.088*
C39	0.09113 (12)	0.8947 (2)	0.15614 (11)	0.0802 (6)
H39	0.0435	0.9157	0.1767	0.096*
C40	0.16735 (11)	0.89347 (17)	0.19143 (9)	0.0643 (5)
H40	0.1709	0.9151	0.2357	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0397 (6)	0.0510 (7)	0.0567 (7)	−0.0069 (5)	−0.0053 (5)	0.0051 (5)
O2	0.0456 (7)	0.0620 (7)	0.0662 (7)	0.0089 (6)	−0.0005 (5)	−0.0102 (6)
O3	0.0580 (7)	0.0580 (7)	0.0662 (8)	0.0094 (6)	−0.0014 (6)	0.0137 (6)
O4	0.0440 (6)	0.0521 (7)	0.0571 (7)	0.0076 (5)	−0.0027 (5)	−0.0035 (5)
O5	0.0493 (7)	0.0567 (8)	0.0914 (9)	−0.0117 (6)	−0.0055 (6)	0.0175 (7)
O6	0.0683 (8)	0.0832 (10)	0.0601 (8)	0.0170 (7)	−0.0152 (6)	−0.0150 (7)
O7	0.0454 (7)	0.0466 (7)	0.0752 (8)	−0.0007 (5)	−0.0010 (6)	0.0014 (6)
O8	0.0701 (9)	0.0579 (8)	0.0620 (8)	−0.0081 (6)	−0.0065 (6)	0.0050 (6)
O9	0.0611 (10)	0.0722 (11)	0.219 (2)	0.0113 (8)	−0.0390 (11)	−0.0493 (12)
C32	0.0429 (9)	0.0467 (9)	0.0550 (9)	0.0005 (7)	−0.0006 (7)	0.0014 (7)
N1	0.0473 (8)	0.0513 (8)	0.0604 (9)	−0.0009 (6)	−0.0017 (6)	0.0010 (7)
N2	0.0406 (8)	0.0531 (8)	0.0607 (8)	0.0064 (6)	−0.0104 (6)	−0.0102 (7)
N3	0.0441 (8)	0.0487 (8)	0.0601 (8)	−0.0004 (6)	−0.0142 (6)	0.0038 (7)
N4	0.0551 (8)	0.0477 (8)	0.0562 (8)	0.0015 (6)	0.0037 (6)	0.0017 (7)
N5	0.0372 (8)	0.0596 (9)	0.0720 (9)	−0.0079 (6)	−0.0072 (7)	0.0169 (8)
N6	0.0380 (8)	0.0620 (9)	0.0566 (9)	−0.0012 (6)	−0.0043 (6)	0.0032 (7)
C1	0.0359 (9)	0.0550 (10)	0.0455 (9)	−0.0034 (7)	0.0000 (7)	−0.0081 (7)
C2	0.0515 (11)	0.0714 (12)	0.0647 (11)	−0.0159 (9)	−0.0032 (8)	0.0026 (9)
C3	0.0503 (11)	0.1031 (17)	0.0816 (14)	−0.0286 (11)	−0.0067 (10)	0.0015 (13)
C4	0.0429 (10)	0.1028 (17)	0.0727 (13)	−0.0044 (10)	−0.0117 (9)	−0.0086 (12)
C5	0.0439 (9)	0.0736 (12)	0.0472 (9)	0.0066 (8)	−0.0036 (7)	−0.0122 (9)
C6	0.0593 (12)	0.0823 (14)	0.0570 (11)	0.0211 (10)	−0.0138 (9)	−0.0087 (10)
C7	0.0827 (14)	0.0671 (13)	0.0640 (12)	0.0142 (11)	−0.0076 (10)	0.0066 (10)
C8	0.0657 (12)	0.0588 (12)	0.0737 (12)	0.0007 (9)	−0.0027 (10)	0.0082 (10)
C9	0.0416 (9)	0.0539 (10)	0.0422 (8)	0.0013 (7)	0.0021 (7)	−0.0110 (7)
C10	0.0509 (10)	0.0429 (9)	0.0611 (10)	−0.0070 (7)	−0.0048 (8)	0.0025 (8)
C11	0.0489 (9)	0.0448 (9)	0.0585 (10)	−0.0003 (7)	−0.0044 (8)	0.0017 (8)
C12	0.0426 (9)	0.0498 (9)	0.0529 (9)	−0.0008 (7)	−0.0038 (7)	0.0001 (7)
C13	0.0423 (9)	0.0434 (9)	0.0440 (8)	0.0009 (7)	−0.0008 (7)	0.0072 (7)
C14	0.0443 (9)	0.0434 (9)	0.0460 (9)	0.0079 (7)	0.0037 (7)	−0.0052 (7)
C15	0.0400 (8)	0.0447 (9)	0.0495 (9)	0.0038 (7)	0.0034 (7)	−0.0071 (7)
C16	0.0481 (10)	0.0582 (11)	0.0720 (12)	−0.0031 (8)	−0.0114 (8)	0.0049 (9)
C17	0.0555 (11)	0.0758 (13)	0.0822 (13)	0.0026 (10)	−0.0176 (10)	0.0069 (11)
C18	0.0447 (10)	0.0932 (16)	0.0782 (13)	−0.0024 (10)	−0.0107 (9)	−0.0159 (12)
C19	0.0543 (12)	0.0820 (15)	0.0958 (15)	−0.0227 (10)	0.0017 (11)	−0.0104 (13)
C20	0.0574 (11)	0.0595 (11)	0.0723 (12)	−0.0049 (9)	0.0032 (9)	0.0036 (9)
C21	0.0428 (9)	0.0526 (10)	0.0439 (8)	0.0025 (7)	0.0005 (7)	0.0072 (7)
C22	0.0515 (10)	0.0618 (11)	0.0608 (11)	0.0121 (8)	−0.0020 (8)	0.0033 (9)
C23	0.0507 (11)	0.0809 (14)	0.0778 (13)	0.0161 (10)	−0.0028 (9)	0.0076 (11)
C24	0.0444 (10)	0.0838 (15)	0.0799 (13)	−0.0020 (10)	−0.0117 (9)	0.0165 (12)
C25	0.0545 (11)	0.0620 (11)	0.0580 (10)	−0.0072 (9)	−0.0022 (8)	0.0137 (9)
C26	0.0701 (13)	0.0741 (14)	0.0737 (13)	−0.0205 (11)	−0.0112 (10)	0.0075 (11)
C27	0.0920 (16)	0.0590 (12)	0.0789 (14)	−0.0139 (11)	−0.0041 (12)	−0.0058 (10)
C28	0.0754 (13)	0.0509 (11)	0.0736 (12)	0.0008 (9)	0.0073 (10)	−0.0005 (9)
C29	0.0455 (9)	0.0524 (10)	0.0458 (9)	−0.0004 (7)	0.0022 (7)	0.0123 (7)
C30	0.0542 (10)	0.0420 (9)	0.0563 (10)	0.0060 (7)	−0.0022 (8)	0.0011 (7)
C31	0.0495 (10)	0.0491 (10)	0.0610 (10)	−0.0016 (7)	−0.0007 (8)	0.0059 (8)
C33	0.0412 (9)	0.0412 (9)	0.0558 (9)	0.0001 (7)	0.0029 (7)	−0.0008 (7)
C34	0.0462 (9)	0.0411 (9)	0.0528 (10)	0.0012 (7)	−0.0032 (7)	0.0053 (7)
C35	0.0429 (9)	0.0407 (8)	0.0503 (9)	−0.0009 (6)	0.0012 (7)	0.0066 (7)
C36	0.0445 (9)	0.0712 (12)	0.0558 (10)	−0.0019 (8)	0.0018 (8)	−0.0003 (9)
C37	0.0561 (12)	0.0871 (14)	0.0576 (11)	−0.0091 (10)	−0.0096 (9)	−0.0021 (10)
C38	0.0456 (11)	0.0863 (15)	0.0843 (14)	−0.0028 (9)	−0.0165 (10)	0.0031 (11)
C39	0.0449 (11)	0.1087 (18)	0.0871 (15)	0.0133 (11)	0.0059 (10)	0.0006 (13)
C40	0.0540 (11)	0.0822 (13)	0.0566 (10)	0.0087 (9)	0.0029 (8)	−0.0019 (9)

Geometric parameters (Å, º)

O1—C1	1.3569 (17)	C11—C12	1.512 (2)
O1—C10	1.4351 (19)	C11—H11A	0.970
O2—C13	1.2282 (18)	C11—H11B	0.970
O3—C14	1.2273 (19)	C12—C13	1.501 (2)
O4—C21	1.3512 (18)	C12—H12A	0.970
O4—C30	1.4397 (19)	C12—H12B	0.970
O5—C33	1.2199 (18)	C14—C15	1.496 (2)
O6—C34	1.2240 (19)	C15—C20	1.379 (2)
O7—H45	0.850	C15—C16	1.381 (2)
O7—H46	0.850	C16—C17	1.380 (2)
O8—H47	0.850	C16—H16	0.930
O8—H48	0.850	C17—C18	1.365 (3)
O9—H49	0.850	C17—H17	0.930
O9—H50	0.850	C18—C19	1.372 (3)
C32—C33	1.499 (2)	C18—H18	0.930
C32—C31	1.507 (2)	C19—C20	1.378 (2)
C32—H32A	0.970	C19—H19	0.930
C32—H32B	0.970	C20—H20	0.930
N1—C8	1.315 (2)	C21—C22	1.366 (2)
N1—C9	1.364 (2)	C21—C29	1.429 (2)
N2—C13	1.337 (2)	C22—C23	1.405 (2)
N2—N3	1.3847 (17)	C22—H22	0.930
N2—H41	0.870	C23—C24	1.357 (3)
N3—C14	1.335 (2)	C23—H23	0.930
N3—H42	0.870	C24—C25	1.416 (3)
N4—C28	1.313 (2)	C24—H24	0.930
N4—C29	1.368 (2)	C25—C26	1.408 (3)
N5—C33	1.339 (2)	C25—C29	1.417 (2)
N5—N6	1.3801 (17)	C26—C27	1.356 (3)
N5—H43	0.870	C26—H26	0.930
N6—C34	1.341 (2)	C27—C28	1.403 (3)
N6—H44	0.870	C27—H27	0.930
C1—C2	1.362 (2)	C28—H28	0.930
C1—C9	1.428 (2)	C30—C31	1.499 (2)
C2—C3	1.414 (3)	C30—H30A	0.970
C2—H2	0.930	C30—H30B	0.970
C3—C4	1.353 (3)	C31—H31A	0.970
C3—H3	0.930	C31—H31B	0.970
C4—C5	1.413 (3)	C34—C35	1.492 (2)
C4—H4	0.930	C35—C40	1.379 (2)
C5—C9	1.413 (2)	C35—C36	1.385 (2)
C5—C6	1.414 (3)	C36—C37	1.376 (2)
C6—C7	1.344 (3)	C36—H36	0.930
C6—H6	0.930	C37—C38	1.367 (3)
C7—C8	1.398 (2)	C37—H37	0.930
C7—H7	0.930	C38—C39	1.371 (3)
C8—H8	0.930	C38—H38	0.930
C10—C11	1.504 (2)	C39—C40	1.375 (3)
C10—H10A	0.970	C39—H39	0.930
C10—H10B	0.970	C40—H40	0.930
C1—O1—C10	117.74 (11)	C17—C16—C15	120.38 (17)
C21—O4—C30	117.26 (12)	C17—C16—H16	119.8
H45—O7—H46	103.8	C15—C16—H16	119.8
H47—O8—H48	105.8	C18—C17—C16	120.59 (19)
H49—O9—H50	106.3	C18—C17—H17	119.7
C33—C32—C31	113.82 (13)	C16—C17—H17	119.7
C33—C32—H32A	108.8	C17—C18—C19	119.49 (17)
C31—C32—H32A	108.8	C17—C18—H18	120.3
C33—C32—H32B	108.8	C19—C18—H18	120.3
C31—C32—H32B	108.8	C18—C19—C20	120.25 (18)
H32A—C32—H32B	107.7	C18—C19—H19	119.9
C8—N1—C9	117.74 (14)	C20—C19—H19	119.9
C13—N2—N3	120.82 (13)	C19—C20—C15	120.67 (18)
C13—N2—H41	122.1	C19—C20—H20	119.7
N3—N2—H41	117.1	C15—C20—H20	119.7
C14—N3—N2	120.83 (13)	O4—C21—C22	125.05 (16)
C14—N3—H42	124.9	O4—C21—C29	115.39 (13)
N2—N3—H42	114.3	C22—C21—C29	119.55 (15)
C28—N4—C29	117.97 (15)	C21—C22—C23	120.58 (18)
C33—N5—N6	120.33 (13)	C21—C22—H22	119.7
C33—N5—H43	122.6	C23—C22—H22	119.7
N6—N5—H43	116.5	C24—C23—C22	121.46 (18)
C34—N6—N5	120.18 (14)	C24—C23—H23	119.3
C34—N6—H44	122.5	C22—C23—H23	119.3
N5—N6—H44	115.8	C23—C24—C25	119.83 (17)
O1—C1—C2	125.05 (16)	C23—C24—H24	120.1
O1—C1—C9	115.13 (13)	C25—C24—H24	120.1
C2—C1—C9	119.82 (15)	C26—C25—C24	123.42 (18)
C1—C2—C3	120.14 (18)	C26—C25—C29	117.21 (17)
C1—C2—H2	119.9	C24—C25—C29	119.36 (18)
C3—C2—H2	119.9	C27—C26—C25	120.08 (18)
C4—C3—C2	121.44 (18)	C27—C26—H26	120.0
C4—C3—H3	119.3	C25—C26—H26	120.0
C2—C3—H3	119.3	C26—C27—C28	118.78 (19)
C3—C4—C5	119.95 (17)	C26—C27—H27	120.6
C3—C4—H4	120.0	C28—C27—H27	120.6
C5—C4—H4	120.0	N4—C28—C27	123.86 (18)
C4—C5—C9	119.40 (17)	N4—C28—H28	118.1
C4—C5—C6	123.56 (17)	C27—C28—H28	118.1
C9—C5—C6	117.04 (16)	N4—C29—C25	122.09 (16)
C7—C6—C5	120.14 (17)	N4—C29—C21	118.71 (14)
C7—C6—H6	119.9	C25—C29—C21	119.20 (15)
C5—C6—H6	119.9	O4—C30—C31	108.85 (12)
C6—C7—C8	118.84 (19)	O4—C30—H30A	109.9
C6—C7—H7	120.6	C31—C30—H30A	109.9
C8—C7—H7	120.6	O4—C30—H30B	109.9
N1—C8—C7	124.05 (18)	C31—C30—H30B	109.9
N1—C8—H8	118.0	H30A—C30—H30B	108.3
C7—C8—H8	118.0	C30—C31—C32	113.30 (13)
N1—C9—C5	122.18 (15)	C30—C31—H31A	108.9
N1—C9—C1	118.58 (13)	C32—C31—H31A	108.9
C5—C9—C1	119.24 (14)	C30—C31—H31B	108.9
O1—C10—C11	108.62 (12)	C32—C31—H31B	108.9
O1—C10—H10A	110.0	H31A—C31—H31B	107.7
C11—C10—H10A	110.0	O5—C33—N5	121.22 (14)
O1—C10—H10B	110.0	O5—C33—C32	125.09 (14)
C11—C10—H10B	110.0	N5—C33—C32	113.68 (13)
H10A—C10—H10B	108.3	O6—C34—N6	122.24 (14)
C10—C11—C12	113.07 (13)	O6—C34—C35	121.01 (14)
C10—C11—H11A	109.0	N6—C34—C35	116.71 (14)
C12—C11—H11A	109.0	C40—C35—C36	118.32 (15)
C10—C11—H11B	109.0	C40—C35—C34	117.32 (14)
C12—C11—H11B	109.0	C36—C35—C34	124.33 (14)
H11A—C11—H11B	107.8	C37—C36—C35	120.55 (16)
C13—C12—C11	113.99 (13)	C37—C36—H36	119.7
C13—C12—H12A	108.8	C35—C36—H36	119.7
C11—C12—H12A	108.8	C38—C37—C36	120.27 (17)
C13—C12—H12B	108.8	C38—C37—H37	119.9
C11—C12—H12B	108.8	C36—C37—H37	119.9
H12A—C12—H12B	107.6	C37—C38—C39	119.92 (17)
O2—C13—N2	121.80 (14)	C37—C38—H38	120.0
O2—C13—C12	124.64 (14)	C39—C38—H38	120.0
N2—C13—C12	113.55 (13)	C38—C39—C40	119.90 (17)
O3—C14—N3	122.38 (14)	C38—C39—H39	120.1
O3—C14—C15	121.54 (14)	C40—C39—H39	120.1
N3—C14—C15	116.07 (13)	C39—C40—C35	121.03 (17)
C20—C15—C16	118.55 (15)	C39—C40—H40	119.5
C20—C15—C14	117.72 (15)	C35—C40—H40	119.5
C16—C15—C14	123.73 (14)
O1—C10—C11—C12	63.19 (18)	C16—C17—C18—C19	2.1 (3)
C10—C11—C12—C13	−179.68 (13)	C17—C18—C19—C20	−2.4 (3)
C11—C12—C13—N2	−168.35 (14)	C18—C19—C20—C15	0.4 (3)
C12—C13—N2—N3	173.14 (13)	C16—C15—C20—C19	1.8 (3)
C13—N2—N3—C14	105.96 (17)	C14—C15—C20—C19	−178.22 (16)
O4—C30—C31—C32	58.75 (18)	C30—O4—C21—C22	−1.0 (2)
C30—C31—C32—C33	170.83 (13)	C30—O4—C21—C29	178.72 (13)
C31—C32—C33—N5	−169.85 (14)	O4—C21—C22—C23	−179.31 (15)
C32—C33—N5—N6	179.26 (14)	C29—C21—C22—C23	1.0 (3)
C33—N5—N6—C34	76.4 (2)	C21—C22—C23—C24	−0.1 (3)
C10—O1—C1—C2	1.0 (2)	C22—C23—C24—C25	0.0 (3)
C10—O1—C1—C9	−179.07 (13)	C23—C24—C25—C26	179.82 (19)
O1—C1—C2—C3	−179.09 (16)	C23—C24—C25—C29	−0.7 (3)
C9—C1—C2—C3	1.0 (3)	C24—C25—C26—C27	178.64 (19)
C1—C2—C3—C4	−0.1 (3)	C29—C25—C26—C27	−0.8 (3)
C2—C3—C4—C5	−0.9 (3)	C25—C26—C27—C28	0.2 (3)
C3—C4—C5—C9	0.9 (3)	C29—N4—C28—C27	−0.7 (3)
C3—C4—C5—C6	−179.18 (19)	C26—C27—C28—N4	0.6 (3)
C4—C5—C6—C7	179.72 (18)	C28—N4—C29—C25	0.0 (2)
C9—C5—C6—C7	−0.4 (3)	C28—N4—C29—C21	179.65 (15)
C5—C6—C7—C8	0.3 (3)	C26—C25—C29—N4	0.7 (2)
C9—N1—C8—C7	0.1 (3)	C24—C25—C29—N4	−178.74 (16)
C6—C7—C8—N1	−0.2 (3)	C26—C25—C29—C21	−178.93 (15)
C8—N1—C9—C5	−0.2 (2)	C24—C25—C29—C21	1.6 (2)
C8—N1—C9—C1	−179.98 (15)	O4—C21—C29—N4	−1.1 (2)
C4—C5—C9—N1	−179.80 (16)	C22—C21—C29—N4	178.60 (15)
C6—C5—C9—N1	0.3 (2)	O4—C21—C29—C25	178.54 (13)
C4—C5—C9—C1	0.0 (2)	C22—C21—C29—C25	−1.7 (2)
C6—C5—C9—C1	−179.91 (14)	C21—O4—C30—C31	−179.50 (12)
O1—C1—C9—N1	−1.1 (2)	N6—N5—C33—O5	−1.9 (2)
C2—C1—C9—N1	178.86 (15)	C31—C32—C33—O5	11.4 (2)
O1—C1—C9—C5	179.12 (12)	N5—N6—C34—O6	4.9 (2)
C2—C1—C9—C5	−1.0 (2)	N5—N6—C34—C35	−177.13 (13)
C1—O1—C10—C11	177.63 (12)	O6—C34—C35—C40	−5.3 (2)
N3—N2—C13—O2	−6.7 (2)	N6—C34—C35—C40	176.74 (15)
C11—C12—C13—O2	11.5 (2)	O6—C34—C35—C36	172.87 (17)
N2—N3—C14—O3	−0.4 (2)	N6—C34—C35—C36	−5.1 (2)
N2—N3—C14—C15	−179.78 (13)	C40—C35—C36—C37	0.7 (3)
O3—C14—C15—C20	3.4 (2)	C34—C35—C36—C37	−177.38 (16)
N3—C14—C15—C20	−177.20 (15)	C35—C36—C37—C38	−0.6 (3)
O3—C14—C15—C16	−176.67 (16)	C36—C37—C38—C39	−0.4 (3)
N3—C14—C15—C16	2.7 (2)	C37—C38—C39—C40	1.3 (3)
C20—C15—C16—C17	−2.1 (3)	C38—C39—C40—C35	−1.2 (3)
C14—C15—C16—C17	177.97 (16)	C36—C35—C40—C39	0.1 (3)
C15—C16—C17—C18	0.1 (3)	C34—C35—C40—C39	178.39 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H41···O3^i	0.87	2.03	2.8699 (18)	161
N3—H42···O8	0.87	1.96	2.7987 (18)	162
N5—H43···O7^ii	0.87	1.90	2.7676 (18)	175
N6—H44···O2^ii	0.87	2.21	2.9941 (19)	150
O7—H45···N1	0.85	2.05	2.8878 (17)	168
O7—H46···O5	0.85	1.89	2.7293 (17)	172
O8—H48···O6^i	0.85	2.02	2.8532 (18)	165
O8—H47···O9	0.85	1.88	2.731 (2)	176
O9—H50···O2^iii	0.85	2.06	2.909 (2)	175
O9—H49···N4^i	0.85	2.05	2.8684 (19)	163

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