4-(2H-1,3-Benzodioxol-5-yl)-1-(4-methyl-phenyl)-1H-pyrazol-5-amine.

In the title compound, C17H15N3O2, two independent mol-ecules (A and B) comprise the asymmetric unit. The major conformational difference arises in the relative orientation of the pyrazole ring amine and dioxole substituents which are anti in A and syn in B. The five-membered dioxole ring in each mol-ecule has an envelope conformation with the methyl-ene C atom as the flap. The mean plane through the benzodioxole and benzene groups make dihedral angles of 31.67 (8) and 68.22 (9)°, respectively, with the pyrazole ring in A; the equivalent values for B are 47.18 (7) and 49.08 (9)°. In the crystal, supra-molecular zigzag chains along the b-axis direction arise as a result of N-H⋯N hydrogen bonding. These are consolidated into supra-molecular double chains via C-H⋯O and C-H⋯π inter-actions.

Related literature

For background to the biological activity of amino substituted pyrazole derivatives, see: Tanitame et al. (2004 ▶); Chimenti et al. (2006 ▶); Ding et al. (2009 ▶); Shen et al. (2011 ▶); Deng et al. (2012 ▶). For a related structure, see: Muruganantham et al. (2007 ▶).

Experimental

Crystal data

C17H15N3O2

M = 293.32

Triclinic,

a = 9.7690 (7) Å

b = 10.4250 (7) Å

c = 14.283 (1) Å

α = 96.626 (2)°

β = 91.903 (2)°

γ = 91.164 (2)°

V = 1443.67 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.40 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.965, T max = 0.982

29089 measured reflections

6620 independent reflections

4674 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.02

6620 reflections

412 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶), QMol (Gans & Shalloway, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009914/su2585sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009914/su2585Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009914/su2585Isup3.cml

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

C17H15N3O2	Z = 4
Mr = 293.32	F(000) = 616
Triclinic, P1	Dx = 1.350 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.7690 (7) Å	Cell parameters from 5105 reflections
b = 10.4250 (7) Å	θ = 2.5–28.1°
c = 14.283 (1) Å	µ = 0.09 mm−1
α = 96.626 (2)°	T = 293 K
β = 91.903 (2)°	Block, light-brown
γ = 91.164 (2)°	0.40 × 0.25 × 0.20 mm
V = 1443.67 (17) Å3

Bruker APEXII CCD diffractometer	6620 independent reflections
Radiation source: fine-focus sealed tube	4674 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.0°
ω and φ scan	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −13→13
Tmin = 0.965, Tmax = 0.982	l = −17→18
29089 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0657P)2 + 0.2775P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
6620 reflections	Δρmax = 0.19 e Å−3
412 parameters	Δρmin = −0.17 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0100 (15)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.05184 (17)	0.01597 (17)	0.34864 (10)	0.0926 (5)
O2	0.05160 (17)	0.22486 (16)	0.42087 (11)	0.0941 (5)
N1	0.56918 (13)	0.17929 (11)	0.77181 (8)	0.0456 (3)
N2	0.56849 (16)	0.29926 (12)	0.74072 (9)	0.0558 (4)
N3	0.46446 (17)	−0.02875 (14)	0.74119 (11)	0.0629 (4)
H1N	0.5319 (15)	−0.0597 (18)	0.7748 (12)	0.075*
H2N	0.4200 (19)	−0.0813 (16)	0.6962 (11)	0.075*
C1	0.8680 (2)	0.1459 (2)	1.11796 (13)	0.0687 (5)
H1A	0.9252	0.0718	1.1123	0.103*
H1B	0.8048	0.1390	1.1673	0.103*
H1C	0.9241	0.2228	1.1328	0.103*
C2	0.78997 (16)	0.15254 (14)	1.02637 (11)	0.0478 (4)
C3	0.85553 (17)	0.16857 (19)	0.94457 (13)	0.0624 (5)
H3	0.9506	0.1765	0.9464	0.075*
C4	0.78454 (17)	0.17326 (18)	0.85982 (12)	0.0583 (4)
H4	0.8314	0.1825	0.8053	0.070*
C5	0.64441 (15)	0.16413 (13)	0.85703 (10)	0.0406 (3)
C6	0.57641 (16)	0.14683 (18)	0.93748 (11)	0.0564 (4)
H6	0.4813	0.1391	0.9355	0.068*
C7	0.64917 (17)	0.14102 (18)	1.02109 (11)	0.0575 (4)
H7	0.6022	0.1291	1.0751	0.069*
C8	0.48562 (15)	0.09408 (13)	0.71784 (10)	0.0415 (3)
C9	0.42651 (15)	0.15896 (13)	0.64773 (9)	0.0404 (3)
C10	0.48195 (18)	0.28428 (15)	0.66748 (10)	0.0513 (4)
H10	0.4597	0.3509	0.6321	0.062*
C11	0.32854 (15)	0.11204 (14)	0.57068 (10)	0.0420 (3)
C12	0.32865 (19)	−0.01296 (16)	0.52498 (12)	0.0569 (4)
H12	0.3908	−0.0707	0.5458	0.068*
C13	0.2395 (2)	−0.05524 (18)	0.44922 (13)	0.0680 (5)
H13	0.2408	−0.1394	0.4195	0.082*
C14	0.15023 (19)	0.03216 (19)	0.42066 (12)	0.0610 (5)
C15	0.14910 (18)	0.15617 (18)	0.46424 (12)	0.0578 (4)
C16	0.23427 (17)	0.19885 (15)	0.53917 (11)	0.0509 (4)
H16	0.2301	0.2830	0.5686	0.061*
C17	−0.0015 (3)	0.1391 (3)	0.34386 (19)	0.1104 (9)
H17A	−0.1007	0.1344	0.3455	0.132*
H17B	0.0230	0.1703	0.2851	0.132*
O3	−0.00982 (14)	0.54440 (13)	−0.17121 (10)	0.0746 (4)
O4	−0.01550 (13)	0.38075 (14)	−0.29402 (9)	0.0685 (4)
N4	0.39249 (13)	0.31673 (12)	0.17245 (9)	0.0458 (3)
N5	0.33173 (15)	0.19573 (12)	0.16344 (10)	0.0563 (4)
N6	0.41337 (19)	0.50194 (14)	0.09039 (10)	0.0634 (4)
H3N	0.427 (2)	0.5557 (16)	0.1430 (9)	0.076*
H4N	0.386 (2)	0.5369 (18)	0.0393 (10)	0.076*
C18	0.7688 (2)	0.4236 (2)	0.48865 (14)	0.0753 (6)
H18A	0.7271	0.3984	0.5438	0.113*
H18B	0.7928	0.5140	0.4987	0.113*
H18C	0.8498	0.3747	0.4765	0.113*
C19	0.66949 (18)	0.39817 (15)	0.40553 (12)	0.0525 (4)
C20	0.70590 (18)	0.42017 (18)	0.31628 (13)	0.0586 (4)
H20	0.7938	0.4516	0.3077	0.070*
C21	0.61593 (17)	0.39708 (17)	0.23905 (12)	0.0534 (4)
H21	0.6435	0.4125	0.1796	0.064*
C22	0.48521 (16)	0.35108 (14)	0.25076 (10)	0.0430 (3)
C23	0.44556 (18)	0.32943 (17)	0.33975 (11)	0.0539 (4)
H23	0.3571	0.2995	0.3486	0.065*
C24	0.5377 (2)	0.35237 (17)	0.41535 (11)	0.0587 (4)
H24	0.5103	0.3365	0.4748	0.070*
C25	0.36066 (16)	0.38099 (14)	0.09701 (10)	0.0418 (3)
C26	0.27733 (15)	0.29921 (14)	0.03560 (10)	0.0427 (3)
C27	0.26475 (17)	0.18800 (15)	0.08121 (12)	0.0532 (4)
H27	0.2137	0.1152	0.0558	0.064*
C28	0.21039 (14)	0.32219 (14)	−0.05457 (10)	0.0424 (3)
C29	0.14039 (16)	0.43657 (15)	−0.06373 (11)	0.0480 (4)
H29	0.1429	0.5044	−0.0153	0.058*
C30	0.06824 (16)	0.44450 (15)	−0.14665 (12)	0.0500 (4)
C31	0.06488 (15)	0.34652 (17)	−0.21981 (11)	0.0487 (4)
C32	0.13435 (16)	0.23582 (17)	−0.21447 (11)	0.0524 (4)
H32	0.1332	0.1702	−0.2645	0.063*
C33	0.20731 (15)	0.22566 (15)	−0.13039 (11)	0.0484 (4)
H33	0.2561	0.1511	−0.1247	0.058*
C34	−0.0848 (2)	0.4919 (2)	−0.25516 (15)	0.0751 (6)
H34A	−0.1776	0.4686	−0.2404	0.090*
H34B	−0.0891	0.5551	−0.2999	0.090*

	U11	U22	U33	U12	U13	U23
O1	0.1014 (11)	0.1036 (12)	0.0658 (9)	−0.0138 (9)	−0.0459 (8)	−0.0029 (8)
O2	0.1030 (11)	0.0994 (11)	0.0758 (10)	0.0264 (9)	−0.0522 (9)	0.0041 (8)
N1	0.0574 (8)	0.0396 (6)	0.0388 (7)	−0.0019 (5)	−0.0142 (6)	0.0058 (5)
N2	0.0851 (10)	0.0404 (7)	0.0410 (7)	−0.0072 (6)	−0.0169 (7)	0.0076 (5)
N3	0.0804 (11)	0.0434 (7)	0.0639 (10)	−0.0094 (7)	−0.0347 (8)	0.0143 (6)
C1	0.0753 (13)	0.0721 (12)	0.0569 (11)	−0.0031 (10)	−0.0314 (9)	0.0100 (9)
C2	0.0530 (9)	0.0442 (8)	0.0448 (8)	−0.0021 (7)	−0.0169 (7)	0.0045 (6)
C3	0.0398 (9)	0.0831 (12)	0.0649 (11)	−0.0149 (8)	−0.0139 (8)	0.0191 (9)
C4	0.0478 (9)	0.0790 (12)	0.0498 (9)	−0.0143 (8)	−0.0029 (7)	0.0188 (8)
C5	0.0467 (8)	0.0388 (7)	0.0352 (7)	−0.0006 (6)	−0.0108 (6)	0.0034 (6)
C6	0.0380 (8)	0.0868 (12)	0.0438 (9)	0.0081 (8)	−0.0041 (7)	0.0053 (8)
C7	0.0527 (10)	0.0838 (12)	0.0359 (8)	0.0059 (9)	−0.0010 (7)	0.0060 (8)
C8	0.0457 (8)	0.0405 (7)	0.0374 (7)	0.0016 (6)	−0.0081 (6)	0.0029 (6)
C9	0.0477 (8)	0.0417 (7)	0.0314 (7)	0.0060 (6)	−0.0039 (6)	0.0027 (6)
C10	0.0778 (11)	0.0413 (8)	0.0344 (8)	0.0026 (7)	−0.0111 (7)	0.0064 (6)
C11	0.0487 (8)	0.0456 (8)	0.0312 (7)	0.0033 (6)	−0.0052 (6)	0.0036 (6)
C12	0.0684 (11)	0.0495 (9)	0.0505 (9)	0.0083 (8)	−0.0148 (8)	−0.0011 (7)
C13	0.0876 (14)	0.0545 (10)	0.0567 (11)	−0.0033 (9)	−0.0176 (10)	−0.0094 (8)
C14	0.0654 (11)	0.0727 (12)	0.0416 (9)	−0.0104 (9)	−0.0182 (8)	0.0011 (8)
C15	0.0610 (10)	0.0688 (11)	0.0435 (9)	0.0069 (8)	−0.0157 (8)	0.0106 (8)
C16	0.0639 (10)	0.0485 (8)	0.0391 (8)	0.0091 (7)	−0.0119 (7)	0.0018 (6)
C17	0.119 (2)	0.117 (2)	0.0897 (18)	0.0012 (17)	−0.0649 (16)	0.0106 (15)
O3	0.0836 (9)	0.0649 (8)	0.0748 (9)	0.0165 (7)	−0.0190 (7)	0.0105 (6)
O4	0.0636 (8)	0.0895 (10)	0.0523 (7)	0.0004 (7)	−0.0138 (6)	0.0123 (6)
N4	0.0543 (8)	0.0406 (6)	0.0420 (7)	−0.0039 (6)	−0.0040 (6)	0.0051 (5)
N5	0.0611 (9)	0.0426 (7)	0.0653 (9)	−0.0088 (6)	−0.0129 (7)	0.0122 (6)
N6	0.1031 (12)	0.0469 (8)	0.0389 (8)	−0.0208 (8)	−0.0140 (8)	0.0076 (6)
C18	0.0871 (14)	0.0711 (12)	0.0653 (12)	0.0104 (10)	−0.0261 (11)	0.0042 (10)
C19	0.0632 (11)	0.0436 (8)	0.0494 (9)	0.0081 (7)	−0.0097 (8)	0.0023 (7)
C20	0.0499 (9)	0.0651 (11)	0.0609 (11)	−0.0029 (8)	−0.0042 (8)	0.0102 (8)
C21	0.0544 (10)	0.0629 (10)	0.0440 (9)	−0.0031 (8)	0.0029 (7)	0.0109 (7)
C22	0.0523 (9)	0.0383 (7)	0.0379 (8)	0.0025 (6)	−0.0025 (6)	0.0028 (6)
C23	0.0564 (10)	0.0600 (10)	0.0450 (9)	−0.0057 (8)	0.0047 (7)	0.0055 (7)
C24	0.0777 (12)	0.0623 (10)	0.0360 (8)	0.0017 (9)	0.0020 (8)	0.0058 (7)
C25	0.0510 (8)	0.0396 (7)	0.0340 (7)	0.0004 (6)	0.0014 (6)	0.0005 (6)
C26	0.0402 (8)	0.0420 (8)	0.0440 (8)	0.0027 (6)	−0.0014 (6)	−0.0018 (6)
C27	0.0508 (9)	0.0422 (8)	0.0648 (11)	−0.0065 (7)	−0.0122 (8)	0.0041 (7)
C28	0.0353 (7)	0.0480 (8)	0.0425 (8)	−0.0029 (6)	0.0001 (6)	0.0000 (6)
C29	0.0497 (9)	0.0464 (8)	0.0459 (8)	0.0007 (7)	−0.0007 (7)	−0.0025 (6)
C30	0.0478 (9)	0.0492 (9)	0.0535 (9)	0.0018 (7)	−0.0012 (7)	0.0088 (7)
C31	0.0394 (8)	0.0666 (10)	0.0399 (8)	−0.0067 (7)	−0.0023 (6)	0.0070 (7)
C32	0.0455 (9)	0.0631 (10)	0.0444 (9)	−0.0042 (7)	0.0002 (7)	−0.0098 (7)
C33	0.0403 (8)	0.0503 (9)	0.0517 (9)	0.0030 (6)	−0.0020 (7)	−0.0061 (7)
C34	0.0674 (12)	0.0865 (14)	0.0729 (13)	0.0056 (11)	−0.0168 (10)	0.0199 (11)

O1—C14	1.378 (2)	O3—C30	1.3741 (19)
O1—C17	1.403 (3)	O3—C34	1.431 (2)
O2—C15	1.376 (2)	O4—C31	1.3824 (19)
O2—C17	1.413 (3)	O4—C34	1.421 (3)
N1—C8	1.3492 (18)	N4—C25	1.3635 (18)
N1—N2	1.3746 (17)	N4—N5	1.3737 (18)
N1—C5	1.4270 (17)	N4—C22	1.4237 (19)
N2—C10	1.3159 (19)	N5—C27	1.319 (2)
N3—C8	1.373 (2)	N6—C25	1.367 (2)
N3—H1N	0.890 (9)	N6—H3N	0.889 (9)
N3—H2N	0.891 (9)	N6—H4N	0.888 (9)
C1—C2	1.501 (2)	C18—C19	1.504 (2)
C1—H1A	0.9600	C18—H18A	0.9600
C1—H1B	0.9600	C18—H18B	0.9600
C1—H1C	0.9600	C18—H18C	0.9600
C2—C3	1.376 (2)	C19—C20	1.378 (2)
C2—C7	1.377 (2)	C19—C24	1.381 (3)
C3—C4	1.381 (2)	C20—C21	1.383 (2)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.369 (2)	C21—C22	1.377 (2)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.374 (2)	C22—C23	1.383 (2)
C6—C7	1.377 (2)	C23—C24	1.379 (2)
C6—H6	0.9300	C23—H23	0.9300
C7—H7	0.9300	C24—H24	0.9300
C8—C9	1.3884 (19)	C25—C26	1.382 (2)
C9—C10	1.398 (2)	C26—C27	1.399 (2)
C9—C11	1.4674 (19)	C26—C28	1.472 (2)
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.389 (2)	C28—C33	1.390 (2)
C11—C16	1.404 (2)	C28—C29	1.403 (2)
C12—C13	1.391 (2)	C29—C30	1.370 (2)
C12—H12	0.9300	C29—H29	0.9300
C13—C14	1.361 (3)	C30—C31	1.374 (2)
C13—H13	0.9300	C31—C32	1.359 (2)
C14—C15	1.369 (3)	C32—C33	1.392 (2)
C15—C16	1.361 (2)	C32—H32	0.9300
C16—H16	0.9300	C33—H33	0.9300
C17—H17A	0.9700	C34—H34A	0.9700
C17—H17B	0.9700	C34—H34B	0.9700
C14—O1—C17	105.27 (16)	C30—O3—C34	104.72 (14)
C15—O2—C17	105.11 (17)	C31—O4—C34	104.44 (13)
C8—N1—N2	111.81 (12)	C25—N4—N5	111.66 (12)
C8—N1—C5	129.50 (12)	C25—N4—C22	130.28 (12)
N2—N1—C5	118.45 (12)	N5—N4—C22	117.78 (12)
C10—N2—N1	103.64 (12)	C27—N5—N4	103.58 (12)
C8—N3—H1N	115.8 (13)	C25—N6—H3N	118.6 (13)
C8—N3—H2N	113.6 (13)	C25—N6—H4N	115.1 (13)
H1N—N3—H2N	119.2 (19)	H3N—N6—H4N	116.5 (19)
C2—C1—H1A	109.5	C19—C18—H18A	109.5
C2—C1—H1B	109.5	C19—C18—H18B	109.5
H1A—C1—H1B	109.5	H18A—C18—H18B	109.5
C2—C1—H1C	109.5	C19—C18—H18C	109.5
H1A—C1—H1C	109.5	H18A—C18—H18C	109.5
H1B—C1—H1C	109.5	H18B—C18—H18C	109.5
C3—C2—C7	117.43 (14)	C20—C19—C24	117.10 (15)
C3—C2—C1	121.71 (15)	C20—C19—C18	121.41 (17)
C7—C2—C1	120.86 (16)	C24—C19—C18	121.49 (16)
C2—C3—C4	122.06 (15)	C19—C20—C21	122.14 (17)
C2—C3—H3	119.0	C19—C20—H20	118.9
C4—C3—H3	119.0	C21—C20—H20	118.9
C5—C4—C3	119.24 (16)	C22—C21—C20	119.58 (15)
C5—C4—H4	120.4	C22—C21—H21	120.2
C3—C4—H4	120.4	C20—C21—H21	120.2
C4—C5—C6	119.89 (14)	C21—C22—C23	119.46 (15)
C4—C5—N1	119.88 (14)	C21—C22—N4	121.55 (13)
C6—C5—N1	120.15 (13)	C23—C22—N4	118.85 (14)
C5—C6—C7	119.95 (15)	C24—C23—C22	119.72 (16)
C5—C6—H6	120.0	C24—C23—H23	120.1
C7—C6—H6	120.0	C22—C23—H23	120.1
C2—C7—C6	121.39 (15)	C23—C24—C19	121.99 (15)
C2—C7—H7	119.3	C23—C24—H24	119.0
C6—C7—H7	119.3	C19—C24—H24	119.0
N1—C8—N3	120.78 (13)	N4—C25—N6	121.33 (13)
N1—C8—C9	107.35 (12)	N4—C25—C26	107.16 (13)
N3—C8—C9	131.66 (14)	N6—C25—C26	131.45 (14)
C8—C9—C10	103.36 (12)	C25—C26—C27	103.66 (13)
C8—C9—C11	129.93 (13)	C25—C26—C28	129.50 (14)
C10—C9—C11	126.70 (13)	C27—C26—C28	126.78 (14)
N2—C10—C9	113.82 (13)	N5—C27—C26	113.94 (14)
N2—C10—H10	123.1	N5—C27—H27	123.0
C9—C10—H10	123.1	C26—C27—H27	123.0
C12—C11—C16	118.51 (14)	C33—C28—C29	118.87 (14)
C12—C11—C9	122.89 (13)	C33—C28—C26	119.78 (13)
C16—C11—C9	118.54 (13)	C29—C28—C26	121.19 (13)
C11—C12—C13	122.64 (15)	C30—C29—C28	117.52 (14)
C11—C12—H12	118.7	C30—C29—H29	121.2
C13—C12—H12	118.7	C28—C29—H29	121.2
C14—C13—C12	116.94 (16)	C29—C30—C31	122.34 (15)
C14—C13—H13	121.5	C29—C30—O3	128.16 (15)
C12—C13—H13	121.5	C31—C30—O3	109.50 (14)
C13—C14—C15	121.39 (15)	C32—C31—C30	121.80 (15)
C13—C14—O1	128.86 (17)	C32—C31—O4	128.42 (15)
C15—C14—O1	109.75 (16)	C30—C31—O4	109.78 (15)
C16—C15—C14	122.54 (15)	C31—C32—C33	116.63 (14)
C16—C15—O2	127.73 (17)	C31—C32—H32	121.7
C14—C15—O2	109.74 (15)	C33—C32—H32	121.7
C15—C16—C11	117.97 (15)	C28—C33—C32	122.80 (15)
C15—C16—H16	121.0	C28—C33—H33	118.6
C11—C16—H16	121.0	C32—C33—H33	118.6
O1—C17—O2	109.53 (17)	O4—C34—O3	107.51 (14)
O1—C17—H17A	109.8	O4—C34—H34A	110.2
O2—C17—H17A	109.8	O3—C34—H34A	110.2
O1—C17—H17B	109.8	O4—C34—H34B	110.2
O2—C17—H17B	109.8	O3—C34—H34B	110.2
H17A—C17—H17B	108.2	H34A—C34—H34B	108.5
C8—N1—N2—C10	0.48 (18)	C25—N4—N5—C27	0.77 (18)
C5—N1—N2—C10	−174.38 (13)	C22—N4—N5—C27	−173.75 (13)
C7—C2—C3—C4	0.1 (3)	C24—C19—C20—C21	−0.4 (3)
C1—C2—C3—C4	179.25 (17)	C18—C19—C20—C21	179.89 (16)
C2—C3—C4—C5	1.2 (3)	C19—C20—C21—C22	0.3 (3)
C3—C4—C5—C6	−1.8 (3)	C20—C21—C22—C23	0.4 (2)
C3—C4—C5—N1	174.93 (15)	C20—C21—C22—N4	−175.21 (14)
C8—N1—C5—C4	117.59 (19)	C25—N4—C22—C21	−46.4 (2)
N2—N1—C5—C4	−68.6 (2)	N5—N4—C22—C21	126.91 (16)
C8—N1—C5—C6	−65.7 (2)	C25—N4—C22—C23	137.94 (17)
N2—N1—C5—C6	108.15 (18)	N5—N4—C22—C23	−48.74 (19)
C4—C5—C6—C7	1.2 (3)	C21—C22—C23—C24	−0.9 (2)
N1—C5—C6—C7	−175.60 (15)	N4—C22—C23—C24	174.84 (14)
C3—C2—C7—C6	−0.8 (3)	C22—C23—C24—C19	0.7 (3)
C1—C2—C7—C6	−179.96 (17)	C20—C19—C24—C23	−0.1 (3)
C5—C6—C7—C2	0.2 (3)	C18—C19—C24—C23	179.61 (16)
N2—N1—C8—N3	−175.36 (15)	N5—N4—C25—N6	−178.24 (15)
C5—N1—C8—N3	−1.2 (2)	C22—N4—C25—N6	−4.6 (2)
N2—N1—C8—C9	0.06 (18)	N5—N4—C25—C26	−0.68 (17)
C5—N1—C8—C9	174.19 (14)	C22—N4—C25—C26	172.97 (14)
N1—C8—C9—C10	−0.53 (17)	N4—C25—C26—C27	0.29 (16)
N3—C8—C9—C10	174.19 (18)	N6—C25—C26—C27	177.51 (18)
N1—C8—C9—C11	179.89 (14)	N4—C25—C26—C28	177.61 (14)
N3—C8—C9—C11	−5.4 (3)	N6—C25—C26—C28	−5.2 (3)
N1—N2—C10—C9	−0.85 (19)	N4—N5—C27—C26	−0.59 (19)
C8—C9—C10—N2	0.89 (19)	C25—C26—C27—N5	0.20 (19)
C11—C9—C10—N2	−179.51 (14)	C28—C26—C27—N5	−177.22 (14)
C8—C9—C11—C12	−34.1 (2)	C25—C26—C28—C33	138.92 (16)
C10—C9—C11—C12	146.40 (18)	C27—C26—C28—C33	−44.3 (2)
C8—C9—C11—C16	148.63 (16)	C25—C26—C28—C29	−45.8 (2)
C10—C9—C11—C16	−30.9 (2)	C27—C26—C28—C29	130.89 (17)
C16—C11—C12—C13	0.2 (3)	C33—C28—C29—C30	2.3 (2)
C9—C11—C12—C13	−177.07 (17)	C26—C28—C29—C30	−172.96 (14)
C11—C12—C13—C14	0.1 (3)	C28—C29—C30—C31	−1.2 (2)
C12—C13—C14—C15	0.4 (3)	C28—C29—C30—O3	178.57 (16)
C12—C13—C14—O1	−179.75 (19)	C34—O3—C30—C29	−167.77 (18)
C17—O1—C14—C13	−174.4 (2)	C34—O3—C30—C31	11.99 (19)
C17—O1—C14—C15	5.4 (2)	C29—C30—C31—C32	−0.6 (3)
C13—C14—C15—C16	−1.3 (3)	O3—C30—C31—C32	179.63 (15)
O1—C14—C15—C16	178.84 (17)	C29—C30—C31—O4	179.92 (15)
C13—C14—C15—O2	178.86 (19)	O3—C30—C31—O4	0.15 (19)
O1—C14—C15—O2	−1.0 (2)	C34—O4—C31—C32	168.27 (18)
C17—O2—C15—C16	176.4 (2)	C34—O4—C31—C30	−12.29 (19)
C17—O2—C15—C14	−3.8 (3)	C30—C31—C32—C33	1.1 (2)
C14—C15—C16—C11	1.6 (3)	O4—C31—C32—C33	−179.54 (15)
O2—C15—C16—C11	−178.62 (18)	C29—C28—C33—C32	−1.9 (2)
C12—C11—C16—C15	−1.0 (2)	C26—C28—C33—C32	173.45 (14)
C9—C11—C16—C15	176.39 (15)	C31—C32—C33—C28	0.2 (2)
C14—O1—C17—O2	−7.8 (3)	C31—O4—C34—O3	19.6 (2)
C15—O2—C17—O1	7.2 (3)	C30—O3—C34—O4	−19.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···N5i	0.89 (2)	2.20 (2)	3.059 (2)	161 (2)
N6—H3N···N2ii	0.89 (1)	2.11 (1)	2.9914 (19)	170 (2)
C1—H1C···O3ii	0.96	2.54	3.479 (2)	164
C3—H3···Cg1iii	0.93	2.83	3.5365 (19)	133
C10—H10···Cg2ii	0.93	2.88	3.6055 (17)	135
C27—H27···Cg3i	0.93	2.94	3.5903 (18)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg1–Cg3 are the centroids of the C28–C33, C19–C24 and C2–C7 rings, respectviely.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N⋯N5i	0.89 (2)	2.20 (2)	3.059 (2)	161 (2)
N6—H3N⋯N2ii	0.89 (1)	2.11 (1)	2.9914 (19)	170 (2)
C1—H1C⋯O3ii	0.96	2.54	3.479 (2)	164
C3—H3⋯Cg1iii	0.93	2.83	3.5365 (19)	133
C10—H10⋯Cg2ii	0.93	2.88	3.6055 (17)	135
C27—H27⋯Cg3i	0.93	2.94	3.5903 (18)	128

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