4'-Chloro-3',5'-dimethoxy-acetanilide.

The title compound, C(10)H(12)ClNO(3), crystallizes with four independent mol-ecules in the asymmetric unit which are linked by inter-molecular N-H⋯O hydrogen bonds.

Related literature

The natural pyran­oacridone acronycine, which can be synthesized from the title compound, exhibits a broad spectrum of activity against numerous experimental tumor models, see: Nguyen et al. (2006 ▶). For a related structure, see: Lai et al. (2007 ▶).

Experimental

Crystal data

C10H12ClNO3

M = 229.66

Monoclinic,

a = 11.1373 (14) Å

b = 15.1159 (19) Å

c = 14.2802 (18) Å

β = 111.9280 (10)°

V = 2230.1 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.908, T max = 0.937

11396 measured reflections

6377 independent reflections

5985 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.105

S = 1.07

6377 reflections

570 parameters

38 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 2293 Friedel pairs

Flack parameter: −0.02 (5)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536809013166/fl2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013166/fl2238Isup2.hkl

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

C10H12ClNO3	Dx = 1.368 Mg m−3
Mr = 229.66	Melting point: 493 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 11.1373 (14) Å	Cell parameters from 7547 reflections
b = 15.1159 (19) Å	θ = 2.4–27.2°
c = 14.2802 (18) Å	µ = 0.33 mm−1
β = 111.928 (1)°	T = 296 K
V = 2230.1 (5) Å3	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm
F(000) = 960

Bruker SMART CCD area-detector diffractometer	6377 independent reflections
Radiation source: fine-focus sealed tube	5985 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→13
Tmin = 0.908, Tmax = 0.937	k = −13→17
11396 measured reflections	l = −16→16

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.5909P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.105	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.25 e Å−3
6377 reflections	Δρmin = −0.17 e Å−3
570 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
38 restraints	Extinction coefficient: 0.0059 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2293 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.02 (5)

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
Cl1	0.50814 (9)	0.60141 (6)	0.49262 (8)	0.0642 (3)
O1	0.2442 (2)	0.54965 (16)	0.3810 (2)	0.0611 (6)
O2	0.1586 (3)	0.97634 (19)	0.3086 (2)	0.0662 (7)
O3	0.5250 (2)	0.78822 (18)	0.4969 (2)	0.0568 (6)
N1	0.0655 (3)	0.8428 (2)	0.3098 (2)	0.0503 (7)
C1	0.1754 (3)	0.7879 (2)	0.3532 (2)	0.0421 (7)
C2	0.2992 (3)	0.8216 (2)	0.4038 (2)	0.0424 (7)
H2	0.3133	0.8824	0.4097	0.051*
C3	0.4001 (3)	0.7634 (2)	0.4448 (2)	0.0421 (7)
C4	0.3794 (3)	0.6724 (2)	0.4367 (2)	0.0440 (7)
C5	0.2560 (3)	0.6400 (2)	0.3866 (2)	0.0455 (7)
C6	0.1529 (3)	0.6973 (2)	0.3435 (2)	0.0462 (7)
H6	0.0701	0.6755	0.3086	0.055*
C7	0.1193 (4)	0.5133 (3)	0.3338 (4)	0.0762 (12)
H7A	0.0653	0.5320	0.3691	0.114*
H7B	0.1249	0.4499	0.3350	0.114*
H7C	0.0826	0.5333	0.2651	0.114*
C8	0.0608 (3)	0.9307 (3)	0.2914 (3)	0.0535 (8)
C9	−0.0731 (4)	0.9684 (3)	0.2456 (4)	0.0721 (12)
H9A	−0.0679	1.0316	0.2405	0.108*
H9B	−0.1207	0.9541	0.2874	0.108*
H9C	−0.1163	0.9438	0.1795	0.108*
C10	0.5538 (4)	0.8806 (3)	0.5012 (3)	0.0665 (11)
H10A	0.5279	0.9037	0.4339	0.100*
H10B	0.6451	0.8893	0.5361	0.100*
H10C	0.5077	0.9108	0.5366	0.100*
Cl2	0.55954 (10)	−0.15609 (7)	0.01677 (8)	0.0650 (3)
O4	0.3842 (2)	−0.20909 (15)	0.11098 (18)	0.0527 (6)
O5	0.3629 (2)	0.21934 (17)	0.1938 (2)	0.0605 (6)
O6	0.5970 (3)	0.03091 (19)	0.0383 (2)	0.0683 (7)
N2	0.3041 (3)	0.07914 (18)	0.2169 (2)	0.0441 (6)
C11	0.3702 (3)	0.0277 (2)	0.1693 (2)	0.0399 (7)
C12	0.3470 (3)	−0.0642 (2)	0.1676 (2)	0.0420 (7)
H12	0.2938	−0.0870	0.1986	0.050*
C13	0.4040 (3)	−0.1200 (2)	0.1194 (2)	0.0415 (7)
C14	0.4881 (3)	−0.0857 (2)	0.0775 (2)	0.0460 (7)
C15	0.5123 (3)	0.0043 (2)	0.0808 (2)	0.0457 (7)
C16	0.4517 (3)	0.0612 (2)	0.1258 (2)	0.0460 (7)
H16	0.4662	0.1218	0.1264	0.055*
C17	0.6186 (5)	0.1241 (3)	0.0333 (4)	0.0850 (15)
H17A	0.5369	0.1539	0.0039	0.128*
H17B	0.6689	0.1342	−0.0075	0.128*
H17C	0.6643	0.1466	0.1001	0.128*
C18	0.3005 (3)	0.1681 (2)	0.2249 (3)	0.0502 (8)
C19	0.2165 (4)	0.2013 (3)	0.2789 (3)	0.0629 (10)
H19A	0.2691	0.2130	0.3483	0.094*
H19B	0.1529	0.1573	0.2757	0.094*
H19C	0.1738	0.2547	0.2474	0.094*
C20	0.2957 (4)	−0.2457 (3)	0.1515 (3)	0.0606 (10)
H20A	0.3300	−0.2388	0.2236	0.091*
H20B	0.2834	−0.3074	0.1349	0.091*
H20C	0.2142	−0.2155	0.1233	0.091*
Cl3	0.01359 (8)	−0.00462 (6)	1.02777 (6)	0.0524 (2)
O7	0.0568 (2)	0.18003 (16)	1.00635 (18)	0.0531 (6)
O8	0.1927 (2)	0.27104 (18)	0.73842 (19)	0.0609 (7)
O9	0.1311 (3)	−0.10568 (15)	0.91356 (18)	0.0538 (6)
N3	0.3026 (3)	0.1427 (2)	0.7915 (2)	0.0451 (6)
C21	0.2327 (3)	0.1090 (2)	0.8477 (2)	0.0392 (7)
C22	0.1802 (3)	0.1657 (2)	0.8994 (2)	0.0423 (7)
H22	0.1904	0.2266	0.8972	0.051*
C23	0.1126 (3)	0.1297 (2)	0.9542 (2)	0.0412 (7)
C24	0.0979 (3)	0.0387 (2)	0.9583 (2)	0.0389 (6)
C25	0.1523 (3)	−0.0168 (2)	0.9073 (2)	0.0405 (7)
C26	0.2202 (3)	0.0183 (2)	0.8522 (2)	0.0428 (7)
H26	0.2570	−0.0189	0.8185	0.051*
C27	0.1790 (5)	−0.1637 (3)	0.8574 (3)	0.0682 (11)
H27A	0.1397	−0.1494	0.7869	0.102*
H27B	0.1584	−0.2237	0.8678	0.102*
H27C	0.2712	−0.1572	0.8795	0.102*
C28	0.2784 (3)	0.2203 (2)	0.7393 (2)	0.0454 (7)
C29	0.3613 (3)	0.2385 (3)	0.6798 (3)	0.0573 (9)
H29A	0.3143	0.2242	0.6102	0.086*
H29B	0.4383	0.2031	0.7055	0.086*
H29C	0.3846	0.3000	0.6856	0.086*
C30	0.0697 (4)	0.2730 (2)	1.0017 (3)	0.0606 (9)
H30A	0.1596	0.2887	1.0307	0.091*
H30B	0.0240	0.3014	1.0386	0.091*
H30C	0.0342	0.2919	0.9325	0.091*
Cl4	1.03856 (8)	0.29948 (8)	0.49008 (8)	0.0684 (3)
O10	0.8345 (2)	0.17496 (18)	0.3899 (2)	0.0619 (7)
O11	0.4972 (2)	0.53597 (17)	0.23430 (19)	0.0573 (6)
O12	0.9289 (2)	0.47290 (17)	0.47789 (18)	0.0566 (6)
N4	0.4909 (2)	0.38854 (19)	0.2602 (2)	0.0429 (6)
C31	0.6224 (3)	0.3698 (2)	0.3182 (2)	0.0361 (6)
C32	0.6607 (3)	0.2822 (2)	0.3235 (2)	0.0430 (7)
H32	0.6014	0.2386	0.2899	0.052*
C33	0.7887 (3)	0.2602 (2)	0.3797 (2)	0.0457 (7)
C34	0.8772 (3)	0.3252 (2)	0.4263 (2)	0.0437 (7)
C35	0.8372 (3)	0.4127 (2)	0.4242 (2)	0.0410 (7)
C36	0.7081 (3)	0.4349 (2)	0.3696 (2)	0.0403 (7)
H36	0.6803	0.4931	0.3679	0.048*
C37	0.8871 (4)	0.5614 (3)	0.4803 (3)	0.0678 (11)
H37A	0.8620	0.5870	0.4142	0.102*
H37B	0.9566	0.5953	0.5271	0.102*
H37C	0.8146	0.5618	0.5012	0.102*
C38	0.4380 (3)	0.4664 (2)	0.2209 (2)	0.0426 (7)
C39	0.2963 (3)	0.4632 (3)	0.1571 (3)	0.0570 (9)
H39A	0.2558	0.5171	0.1654	0.086*
H39B	0.2572	0.4140	0.1774	0.086*
H39C	0.2850	0.4565	0.0874	0.086*
C40	0.7423 (4)	0.1055 (3)	0.3627 (3)	0.0641 (10)
H40A	0.6810	0.1147	0.3945	0.096*
H40B	0.7856	0.0500	0.3845	0.096*
H40C	0.6977	0.1048	0.2907	0.096*
H3A	0.361 (3)	0.109 (2)	0.786 (2)	0.039 (8)*
H2A	0.261 (3)	0.047 (2)	0.247 (3)	0.055 (10)*
H1A	−0.008 (4)	0.819 (3)	0.295 (3)	0.055 (11)*
H4A	0.440 (3)	0.346 (3)	0.235 (3)	0.050 (10)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0549 (5)	0.0394 (5)	0.0880 (6)	0.0025 (4)	0.0147 (4)	0.0066 (5)
O1	0.0557 (13)	0.0326 (14)	0.0833 (16)	−0.0071 (11)	0.0123 (12)	−0.0004 (12)
O2	0.0690 (16)	0.0501 (17)	0.0882 (18)	0.0024 (13)	0.0392 (14)	0.0134 (14)
O3	0.0495 (12)	0.0405 (15)	0.0749 (15)	−0.0088 (11)	0.0167 (11)	−0.0075 (12)
N1	0.0492 (16)	0.0429 (17)	0.0614 (17)	0.0034 (14)	0.0237 (14)	0.0054 (14)
C1	0.0497 (16)	0.0368 (19)	0.0453 (16)	0.0035 (14)	0.0241 (13)	0.0041 (14)
C2	0.0546 (17)	0.0311 (17)	0.0483 (16)	−0.0007 (14)	0.0271 (14)	−0.0018 (13)
C3	0.0442 (16)	0.0391 (19)	0.0463 (16)	−0.0040 (14)	0.0206 (14)	−0.0050 (14)
C4	0.0514 (17)	0.0325 (17)	0.0494 (17)	−0.0002 (14)	0.0204 (14)	−0.0004 (14)
C5	0.0557 (18)	0.0305 (17)	0.0524 (18)	−0.0046 (14)	0.0227 (15)	0.0050 (14)
C6	0.0453 (16)	0.041 (2)	0.0520 (17)	−0.0029 (15)	0.0184 (14)	−0.0011 (15)
C7	0.065 (2)	0.039 (2)	0.116 (3)	−0.0170 (19)	0.025 (2)	−0.006 (2)
C8	0.0609 (19)	0.049 (2)	0.062 (2)	0.0056 (18)	0.0365 (17)	0.0046 (18)
C9	0.071 (2)	0.058 (3)	0.095 (3)	0.019 (2)	0.041 (2)	0.018 (2)
C10	0.064 (2)	0.043 (2)	0.089 (3)	−0.0149 (18)	0.024 (2)	−0.008 (2)
Cl2	0.0837 (6)	0.0467 (5)	0.0848 (6)	0.0072 (5)	0.0548 (5)	0.0030 (5)
O4	0.0759 (15)	0.0264 (12)	0.0671 (14)	−0.0033 (11)	0.0398 (12)	−0.0016 (11)
O5	0.0622 (14)	0.0320 (14)	0.0868 (18)	−0.0095 (12)	0.0270 (13)	−0.0055 (13)
O6	0.0870 (18)	0.0430 (15)	0.0985 (19)	−0.0058 (14)	0.0619 (16)	0.0053 (14)
N2	0.0515 (14)	0.0282 (15)	0.0535 (15)	−0.0054 (12)	0.0206 (12)	−0.0033 (11)
C11	0.0403 (15)	0.0311 (17)	0.0436 (15)	−0.0012 (12)	0.0101 (12)	−0.0014 (13)
C12	0.0457 (15)	0.0331 (18)	0.0474 (16)	−0.0024 (14)	0.0175 (13)	0.0006 (14)
C13	0.0505 (16)	0.0300 (17)	0.0429 (15)	−0.0021 (13)	0.0160 (13)	0.0027 (13)
C14	0.0504 (16)	0.0415 (19)	0.0465 (16)	0.0045 (15)	0.0186 (14)	0.0042 (14)
C15	0.0467 (16)	0.0377 (18)	0.0533 (17)	−0.0019 (14)	0.0192 (14)	0.0093 (15)
C16	0.0492 (16)	0.0326 (18)	0.0502 (16)	−0.0017 (14)	0.0117 (14)	0.0044 (14)
C17	0.121 (4)	0.055 (3)	0.106 (3)	−0.027 (3)	0.074 (3)	0.002 (3)
C18	0.0464 (16)	0.0361 (19)	0.060 (2)	0.0015 (15)	0.0103 (15)	−0.0037 (16)
C19	0.074 (2)	0.040 (2)	0.078 (2)	0.0051 (18)	0.032 (2)	−0.0058 (19)
C20	0.086 (3)	0.039 (2)	0.073 (2)	−0.0149 (19)	0.048 (2)	−0.0115 (17)
Cl3	0.0530 (4)	0.0560 (6)	0.0536 (4)	−0.0101 (4)	0.0260 (4)	−0.0017 (4)
O7	0.0646 (14)	0.0405 (14)	0.0654 (14)	0.0032 (11)	0.0370 (12)	−0.0089 (11)
O8	0.0659 (15)	0.0546 (17)	0.0636 (15)	0.0218 (13)	0.0259 (12)	0.0196 (13)
O9	0.0757 (15)	0.0296 (13)	0.0619 (14)	−0.0054 (11)	0.0325 (12)	−0.0049 (10)
N3	0.0457 (14)	0.0422 (17)	0.0514 (15)	0.0054 (13)	0.0230 (12)	0.0058 (12)
C21	0.0375 (14)	0.0394 (18)	0.0391 (14)	0.0013 (13)	0.0123 (12)	0.0017 (14)
C22	0.0469 (16)	0.0300 (17)	0.0499 (17)	0.0006 (13)	0.0180 (14)	0.0005 (13)
C23	0.0390 (14)	0.0423 (19)	0.0407 (15)	0.0026 (13)	0.0132 (12)	−0.0074 (13)
C24	0.0391 (14)	0.0415 (18)	0.0357 (14)	−0.0034 (13)	0.0135 (12)	0.0009 (13)
C25	0.0463 (15)	0.0326 (17)	0.0396 (14)	−0.0005 (13)	0.0125 (12)	−0.0005 (13)
C26	0.0477 (16)	0.0401 (19)	0.0419 (15)	0.0062 (14)	0.0181 (13)	−0.0024 (13)
C27	0.102 (3)	0.035 (2)	0.078 (3)	0.005 (2)	0.046 (2)	−0.0047 (19)
C28	0.0445 (15)	0.044 (2)	0.0424 (15)	−0.0005 (15)	0.0109 (13)	0.0064 (15)
C29	0.0567 (19)	0.056 (2)	0.061 (2)	−0.0024 (18)	0.0250 (17)	0.0147 (18)
C30	0.077 (2)	0.036 (2)	0.075 (2)	0.0081 (17)	0.036 (2)	−0.0091 (18)
Cl4	0.0425 (4)	0.0693 (7)	0.0779 (6)	0.0103 (4)	0.0048 (4)	0.0099 (5)
O10	0.0555 (14)	0.0418 (15)	0.0805 (17)	0.0127 (12)	0.0163 (12)	0.0019 (13)
O11	0.0465 (12)	0.0368 (13)	0.0775 (16)	−0.0083 (11)	0.0106 (11)	0.0043 (12)
O12	0.0441 (12)	0.0495 (16)	0.0607 (13)	−0.0096 (11)	0.0018 (10)	0.0048 (11)
N4	0.0352 (12)	0.0349 (16)	0.0527 (15)	−0.0069 (12)	0.0097 (11)	−0.0019 (12)
C31	0.0365 (13)	0.0358 (18)	0.0352 (13)	−0.0004 (12)	0.0124 (11)	0.0028 (12)
C32	0.0430 (15)	0.0372 (18)	0.0457 (16)	0.0001 (13)	0.0128 (13)	−0.0035 (14)
C33	0.0473 (16)	0.043 (2)	0.0460 (16)	0.0074 (15)	0.0168 (14)	0.0003 (14)
C34	0.0389 (15)	0.048 (2)	0.0422 (15)	0.0054 (14)	0.0124 (12)	0.0085 (14)
C35	0.0404 (15)	0.0426 (19)	0.0367 (14)	−0.0075 (14)	0.0106 (12)	0.0024 (13)
C36	0.0402 (14)	0.0378 (17)	0.0393 (14)	−0.0004 (14)	0.0106 (12)	0.0056 (13)
C37	0.060 (2)	0.047 (2)	0.073 (2)	−0.0112 (18)	−0.0012 (18)	−0.0011 (19)
C38	0.0385 (15)	0.0393 (19)	0.0488 (16)	−0.0008 (14)	0.0149 (13)	−0.0010 (14)
C39	0.0402 (16)	0.047 (2)	0.075 (2)	−0.0010 (15)	0.0111 (16)	−0.0036 (18)
C40	0.074 (2)	0.045 (2)	0.070 (2)	0.008 (2)	0.0227 (19)	−0.0044 (19)

Cl1—C4	1.729 (3)	Cl3—C24	1.729 (3)
O1—C5	1.371 (4)	O7—C23	1.366 (4)
O1—C7	1.412 (5)	O7—C30	1.417 (4)
O2—C8	1.234 (4)	O8—C28	1.220 (4)
O3—C3	1.363 (4)	O9—C25	1.372 (4)
O3—C10	1.428 (5)	O9—C27	1.420 (4)
N1—C8	1.351 (5)	N3—C28	1.361 (4)
N1—C1	1.416 (4)	N3—C21	1.405 (4)
N1—H1A	0.85 (4)	N3—H3A	0.86 (3)
C1—C6	1.390 (5)	C21—C26	1.383 (5)
C1—C2	1.392 (4)	C21—C22	1.394 (4)
C2—C3	1.375 (4)	C22—C23	1.384 (4)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.393 (5)	C23—C24	1.389 (5)
C4—C5	1.381 (5)	C24—C25	1.390 (4)
C5—C6	1.385 (5)	C25—C26	1.384 (4)
C6—H6	0.9300	C26—H26	0.9300
C7—H7A	0.9600	C27—H27A	0.9600
C7—H7B	0.9600	C27—H27B	0.9600
C7—H7C	0.9600	C27—H27C	0.9600
C8—C9	1.500 (5)	C28—C29	1.495 (5)
C9—H9A	0.9600	C29—H29A	0.9600
C9—H9B	0.9600	C29—H29B	0.9600
C9—H9C	0.9600	C29—H29C	0.9600
C10—H10A	0.9600	C30—H30A	0.9600
C10—H10B	0.9600	C30—H30B	0.9600
C10—H10C	0.9600	C30—H30C	0.9600
Cl2—C14	1.741 (3)	Cl4—C34	1.729 (3)
O4—C13	1.362 (4)	O10—C33	1.373 (4)
O4—C20	1.428 (4)	O10—C40	1.418 (5)
O5—C18	1.229 (4)	O11—C38	1.219 (4)
O6—C15	1.359 (4)	O12—C35	1.369 (4)
O6—C17	1.436 (5)	O12—C37	1.421 (5)
N2—C18	1.351 (4)	N4—C38	1.341 (4)
N2—C11	1.408 (4)	N4—C31	1.416 (4)
N2—H2A	0.895 (18)	N4—H4A	0.84 (4)
C11—C16	1.374 (5)	C31—C36	1.376 (4)
C11—C12	1.411 (5)	C31—C32	1.385 (5)
C12—C13	1.384 (5)	C32—C33	1.390 (4)
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.388 (4)	C33—C34	1.375 (5)
C14—C15	1.385 (5)	C34—C35	1.392 (5)
C15—C16	1.390 (5)	C35—C36	1.397 (4)
C16—H16	0.9300	C36—H36	0.9300
C17—H17A	0.9600	C37—H37A	0.9600
C17—H17B	0.9600	C37—H37B	0.9600
C17—H17C	0.9600	C37—H37C	0.9600
C18—C19	1.504 (5)	C38—C39	1.500 (4)
C19—H19A	0.9600	C39—H39A	0.9600
C19—H19B	0.9600	C39—H39B	0.9600
C19—H19C	0.9600	C39—H39C	0.9600
C20—H20A	0.9600	C40—H40A	0.9600
C20—H20B	0.9600	C40—H40B	0.9600
C20—H20C	0.9600	C40—H40C	0.9600
C5—O1—C7	118.1 (3)	C23—O7—C30	116.9 (3)
C3—O3—C10	117.4 (3)	C25—O9—C27	117.2 (3)
C8—N1—C1	128.7 (3)	C28—N3—C21	125.9 (3)
C8—N1—H1A	113 (3)	C28—N3—H3A	117 (2)
C1—N1—H1A	118 (3)	C21—N3—H3A	116 (2)
C6—C1—C2	121.3 (3)	C26—C21—C22	120.9 (3)
C6—C1—N1	116.1 (3)	C26—C21—N3	118.3 (3)
C2—C1—N1	122.6 (3)	C22—C21—N3	120.7 (3)
C3—C2—C1	118.7 (3)	C23—C22—C21	118.9 (3)
C3—C2—H2	120.7	C23—C22—H22	120.6
C1—C2—H2	120.7	C21—C22—H22	120.6
O3—C3—C2	124.2 (3)	O7—C23—C22	122.9 (3)
O3—C3—C4	115.0 (3)	O7—C23—C24	116.4 (3)
C2—C3—C4	120.9 (3)	C22—C23—C24	120.7 (3)
C5—C4—C3	119.7 (3)	C23—C24—C25	119.6 (3)
C5—C4—Cl1	120.9 (3)	C23—C24—Cl3	119.8 (2)
C3—C4—Cl1	119.4 (2)	C25—C24—Cl3	120.6 (3)
O1—C5—C4	116.0 (3)	O9—C25—C26	123.8 (3)
O1—C5—C6	123.5 (3)	O9—C25—C24	115.9 (3)
C4—C5—C6	120.5 (3)	C26—C25—C24	120.2 (3)
C5—C6—C1	118.9 (3)	C21—C26—C25	119.6 (3)
C5—C6—H6	120.5	C21—C26—H26	120.2
C1—C6—H6	120.5	C25—C26—H26	120.2
O1—C7—H7A	109.5	O9—C27—H27A	109.5
O1—C7—H7B	109.5	O9—C27—H27B	109.5
H7A—C7—H7B	109.5	H27A—C27—H27B	109.5
O1—C7—H7C	109.5	O9—C27—H27C	109.5
H7A—C7—H7C	109.5	H27A—C27—H27C	109.5
H7B—C7—H7C	109.5	H27B—C27—H27C	109.5
O2—C8—N1	122.9 (3)	O8—C28—N3	122.8 (3)
O2—C8—C9	122.3 (4)	O8—C28—C29	121.6 (3)
N1—C8—C9	114.8 (3)	N3—C28—C29	115.6 (3)
C8—C9—H9A	109.5	C28—C29—H29A	109.5
C8—C9—H9B	109.5	C28—C29—H29B	109.5
H9A—C9—H9B	109.5	H29A—C29—H29B	109.5
C8—C9—H9C	109.5	C28—C29—H29C	109.5
H9A—C9—H9C	109.5	H29A—C29—H29C	109.5
H9B—C9—H9C	109.5	H29B—C29—H29C	109.5
O3—C10—H10A	109.5	O7—C30—H30A	109.5
O3—C10—H10B	109.5	O7—C30—H30B	109.5
H10A—C10—H10B	109.5	H30A—C30—H30B	109.5
O3—C10—H10C	109.5	O7—C30—H30C	109.5
H10A—C10—H10C	109.5	H30A—C30—H30C	109.5
H10B—C10—H10C	109.5	H30B—C30—H30C	109.5
C13—O4—C20	117.4 (3)	C33—O10—C40	117.6 (3)
C15—O6—C17	118.0 (3)	C35—O12—C37	117.2 (3)
C18—N2—C11	128.9 (3)	C38—N4—C31	128.1 (3)
C18—N2—H2A	118 (2)	C38—N4—H4A	112 (3)
C11—N2—H2A	113 (2)	C31—N4—H4A	119 (3)
C16—C11—N2	124.6 (3)	C36—C31—C32	121.1 (3)
C16—C11—C12	120.1 (3)	C36—C31—N4	121.9 (3)
N2—C11—C12	115.3 (3)	C32—C31—N4	117.0 (3)
C13—C12—C11	119.7 (3)	C31—C32—C33	119.3 (3)
C13—C12—H12	120.2	C31—C32—H32	120.4
C11—C12—H12	120.2	C33—C32—H32	120.4
O4—C13—C12	123.9 (3)	O10—C33—C34	116.6 (3)
O4—C13—C14	116.4 (3)	O10—C33—C32	123.1 (3)
C12—C13—C14	119.7 (3)	C34—C33—C32	120.2 (3)
C15—C14—C13	120.4 (3)	C33—C34—C35	120.2 (3)
C15—C14—Cl2	119.9 (2)	C33—C34—Cl4	120.7 (3)
C13—C14—Cl2	119.6 (3)	C35—C34—Cl4	119.1 (2)
O6—C15—C14	115.7 (3)	O12—C35—C34	117.0 (3)
O6—C15—C16	124.1 (3)	O12—C35—C36	123.4 (3)
C14—C15—C16	120.1 (3)	C34—C35—C36	119.7 (3)
C11—C16—C15	119.9 (3)	C31—C36—C35	119.3 (3)
C11—C16—H16	120.1	C31—C36—H36	120.3
C15—C16—H16	120.1	C35—C36—H36	120.3
O6—C17—H17A	109.5	O12—C37—H37A	109.5
O6—C17—H17B	109.5	O12—C37—H37B	109.5
H17A—C17—H17B	109.5	H37A—C37—H37B	109.5
O6—C17—H17C	109.5	O12—C37—H37C	109.5
H17A—C17—H17C	109.5	H37A—C37—H37C	109.5
H17B—C17—H17C	109.5	H37B—C37—H37C	109.5
O5—C18—N2	123.9 (3)	O11—C38—N4	124.3 (3)
O5—C18—C19	121.3 (3)	O11—C38—C39	120.5 (3)
N2—C18—C19	114.8 (3)	N4—C38—C39	115.1 (3)
C18—C19—H19A	109.5	C38—C39—H39A	109.5
C18—C19—H19B	109.5	C38—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C18—C19—H19C	109.5	C38—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5
O4—C20—H20A	109.5	O10—C40—H40A	109.5
O4—C20—H20B	109.5	O10—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
O4—C20—H20C	109.5	O10—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O11i	0.86 (3)	2.03 (4)	2.886 (4)	176 (3)
N2—H2A···O2ii	0.90 (2)	1.99 (2)	2.887 (4)	178 (3)
N1—H1A···O8iii	0.85 (4)	2.06 (4)	2.906 (4)	176 (4)
N4—H4A···O5	0.84 (4)	2.10 (4)	2.909 (4)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O11i	0.86 (3)	2.03 (4)	2.886 (4)	176 (3)
N2—H2A⋯O2ii	0.895 (18)	1.993 (19)	2.887 (4)	178 (3)
N1—H1A⋯O8iii	0.85 (4)	2.06 (4)	2.906 (4)	176 (4)
N4—H4A⋯O5	0.84 (4)	2.10 (4)	2.909 (4)	163 (3)

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