1,5-Dimethyl-2-phenyl-1H-pyrazol-3(2H)-one-4,4'-(propane-2,2-di-yl)bis-[1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] (1/1).

The asymmetric unit of the title compound, C11H12N2O·C25H28N4O2, contains two different mol-ecules. The smaller is known as anti-pyrine [systematic name: 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] and the larger is built up from two antypirine mol-ecules which are connected through a C atom of the pyrazolone ring to a central propanyl part [systematic name: 4,4'-(propane-2,2-di-yl)bis-[1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one]. Intra-molecular C-H⋯O hydrogen bonds occur in the latter mol-ecule. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network parallel to (001).

Related literature

Structural data on metal complexes with anti­pyrine were reported by Vijayan & Viswamitra (1966 ▶); Biagini Cingi et al. (1972 ▶); Baker & Jeffery (1974 ▶); Brassy et al. (1974 ▶); Mahadevan et al. (1984 ▶); Rheingold & King (1989 ▶) and Su et al. (2000 ▶). For related structures, see: Singh & Vijayan (1973 ▶); Panneerselvam et al. (1996 ▶); Merz (2002 ▶); Yuchi et al. (1991 ▶). Some properties of anti­pyrine and its derivatives were described by Peter et al. (1991 ▶).

Experimental

Crystal data

C11H12N2O·C25H28N4O2

M = 604.74

Monoclinic,

a = 11.1751 (3) Å

b = 7.4623 (2) Å

c = 37.2830 (8) Å

β = 91.570 (2)°

V = 3107.93 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.67 mm−1

T = 100 K

0.30 × 0.25 × 0.15 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.938, T max = 1.000

12009 measured reflections

6009 independent reflections

5366 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.099

S = 1.03

6009 reflections

414 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681205091X/kj2216sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205091X/kj2216Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205091X/kj2216Isup3.cml

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

C25H28N4O2·C11H12N2O	F(000) = 1288
Mr = 604.74	Dx = 1.292 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 5594 reflections
a = 11.1751 (3) Å	θ = 3.6–71.8°
b = 7.4623 (2) Å	µ = 0.67 mm−1
c = 37.2830 (8) Å	T = 100 K
β = 91.570 (2)°	Block, colourless
V = 3107.93 (14) Å3	0.30 × 0.25 × 0.15 mm
Z = 4

Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer	6009 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5366 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.018
Detector resolution: 16.0131 pixels mm-1	θmax = 72.0°, θmin = 4.1°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −4→9
Tmin = 0.938, Tmax = 1.000	l = −45→42
12009 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0422P)2 + 1.6129P] where P = (Fo2 + 2Fc2)/3
6009 reflections	(Δ/σ)max < 0.001
414 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.31 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
C1	0.73885 (12)	0.5494 (2)	0.19813 (4)	0.0176 (3)
C2	0.70121 (13)	0.4021 (2)	0.22001 (4)	0.0201 (3)
H2	0.7288	0.3775	0.2438	0.024*
C3	0.61974 (12)	0.30441 (19)	0.20087 (4)	0.0191 (3)
C4	0.55955 (15)	0.1333 (2)	0.21067 (4)	0.0281 (3)
H4A	0.5944	0.0341	0.1973	0.042*
H4B	0.4738	0.1418	0.2047	0.042*
H4C	0.5710	0.1117	0.2365	0.042*
C5	0.57888 (13)	0.2704 (2)	0.13580 (4)	0.0201 (3)
H5A	0.6543	0.2098	0.1306	0.030*
H5B	0.5546	0.3459	0.1154	0.030*
H5C	0.5167	0.1808	0.1400	0.030*
C6	0.65888 (12)	0.65797 (18)	0.13835 (3)	0.0160 (3)
C7	0.54464 (13)	0.69605 (19)	0.12467 (4)	0.0191 (3)
H7	0.4769	0.6379	0.1342	0.023*
C8	0.53013 (14)	0.8194 (2)	0.09705 (4)	0.0230 (3)
H8	0.4524	0.8436	0.0873	0.028*
C9	0.62883 (15)	0.9074 (2)	0.08366 (4)	0.0246 (3)
H9	0.6188	0.9905	0.0645	0.029*
C10	0.74213 (14)	0.87403 (19)	0.09827 (4)	0.0227 (3)
H10	0.8091	0.9375	0.0896	0.027*
C11	0.75846 (13)	0.74826 (19)	0.12551 (4)	0.0189 (3)
H11	0.8362	0.7241	0.1352	0.023*
N1	0.59546 (10)	0.38236 (16)	0.16795 (3)	0.0166 (2)
N2	0.67665 (10)	0.52572 (16)	0.16531 (3)	0.0161 (2)
O1	0.80765 (9)	0.67590 (15)	0.20421 (3)	0.0244 (2)
C12	0.26030 (12)	0.43381 (19)	0.11446 (4)	0.0179 (3)
H12A	0.2893	0.5128	0.0956	0.027*
H12B	0.3282	0.3712	0.1259	0.027*
H12C	0.2192	0.5053	0.1324	0.027*
C13	0.17264 (11)	0.29586 (17)	0.09789 (3)	0.0139 (3)
C14	0.24097 (12)	0.18958 (19)	0.06911 (4)	0.0182 (3)
H14A	0.1884	0.0971	0.0587	0.027*
H14B	0.3118	0.1329	0.0803	0.027*
H14C	0.2659	0.2716	0.0502	0.027*
C15	0.22095 (12)	0.04833 (18)	0.14514 (3)	0.0154 (3)
C16	0.13547 (11)	0.17061 (17)	0.12818 (3)	0.0137 (3)
C17	0.03074 (12)	0.15149 (18)	0.14544 (3)	0.0143 (3)
C18	−0.08452 (12)	0.2527 (2)	0.14323 (4)	0.0201 (3)
H18A	−0.0899	0.3321	0.1641	0.030*
H18B	−0.1516	0.1682	0.1430	0.030*
H18C	−0.0876	0.3244	0.1212	0.030*
C19	−0.01645 (13)	0.0347 (2)	0.20569 (4)	0.0209 (3)
H19A	0.0201	0.1378	0.2180	0.031*
H19B	−0.0029	−0.0736	0.2201	0.031*
H19C	−0.1027	0.0550	0.2024	0.031*
C20	0.19083 (12)	−0.20882 (18)	0.18707 (3)	0.0163 (3)
C21	0.10387 (13)	−0.3368 (2)	0.19420 (4)	0.0205 (3)
H21	0.0220	−0.3141	0.1883	0.025*
C22	0.13810 (15)	−0.4980 (2)	0.21008 (4)	0.0267 (3)
H22	0.0786	−0.5836	0.2158	0.032*
C23	0.25744 (15)	−0.5362 (2)	0.21774 (4)	0.0279 (3)
H23	0.2800	−0.6475	0.2283	0.034*
C24	0.34341 (14)	−0.4095 (2)	0.20980 (4)	0.0248 (3)
H24	0.4255	−0.4356	0.2145	0.030*
C25	0.31133 (13)	−0.2447 (2)	0.19507 (3)	0.0192 (3)
H25	0.3708	−0.1573	0.1905	0.023*
C26	−0.02192 (11)	0.26949 (18)	0.05944 (3)	0.0137 (3)
C27	0.06521 (11)	0.38047 (18)	0.07869 (3)	0.0135 (3)
C28	0.02835 (11)	0.55412 (18)	0.07508 (3)	0.0138 (3)
C29	0.08036 (13)	0.72665 (18)	0.08890 (4)	0.0189 (3)
H29A	0.0926	0.7190	0.1150	0.028*
H29B	0.0252	0.8252	0.0831	0.028*
H29C	0.1573	0.7486	0.0777	0.028*
C30	−0.10277 (12)	0.69931 (18)	0.02819 (3)	0.0169 (3)
H30A	−0.0781	0.8171	0.0373	0.025*
H30B	−0.1883	0.7018	0.0217	0.025*
H30C	−0.0568	0.6698	0.0070	0.025*
C31	−0.22286 (12)	0.34094 (18)	0.03238 (3)	0.0143 (3)
C32	−0.23650 (13)	0.20851 (19)	0.00621 (4)	0.0176 (3)
H32	−0.1684	0.1509	−0.0032	0.021*
C33	−0.35122 (13)	0.16203 (19)	−0.00586 (4)	0.0204 (3)
H33	−0.3616	0.0719	−0.0237	0.024*
C34	−0.45076 (13)	0.2464 (2)	0.00795 (4)	0.0217 (3)
H34	−0.5288	0.2144	−0.0005	0.026*
C35	−0.43591 (13)	0.37752 (19)	0.03412 (4)	0.0199 (3)
H35	−0.5040	0.4350	0.0436	0.024*
C36	−0.32209 (12)	0.42511 (19)	0.04652 (3)	0.0170 (3)
H36	−0.3120	0.5144	0.0645	0.020*
N3	0.03776 (10)	0.01203 (16)	0.17043 (3)	0.0154 (2)
N4	0.15874 (10)	−0.04046 (16)	0.17199 (3)	0.0160 (2)
N5	−0.08054 (10)	0.56315 (14)	0.05609 (3)	0.0137 (2)
N6	−0.10503 (10)	0.38756 (15)	0.04440 (3)	0.0142 (2)
O2	0.32678 (8)	0.01806 (14)	0.13877 (3)	0.0215 (2)
O3	−0.03072 (9)	0.10492 (12)	0.05679 (3)	0.0181 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0138 (6)	0.0231 (7)	0.0160 (6)	0.0009 (6)	0.0012 (5)	−0.0033 (5)
C2	0.0194 (7)	0.0249 (7)	0.0161 (6)	0.0009 (6)	0.0015 (5)	0.0000 (6)
C3	0.0176 (7)	0.0194 (7)	0.0204 (7)	0.0026 (6)	0.0028 (5)	0.0013 (5)
C4	0.0316 (8)	0.0238 (8)	0.0290 (8)	−0.0051 (7)	0.0001 (6)	0.0059 (6)
C5	0.0169 (7)	0.0216 (7)	0.0218 (7)	−0.0013 (6)	−0.0005 (5)	−0.0064 (6)
C6	0.0189 (7)	0.0148 (6)	0.0142 (6)	0.0003 (5)	0.0023 (5)	−0.0031 (5)
C7	0.0184 (7)	0.0203 (7)	0.0187 (6)	0.0008 (6)	0.0028 (5)	−0.0022 (5)
C8	0.0255 (8)	0.0229 (7)	0.0204 (7)	0.0082 (6)	−0.0002 (6)	−0.0022 (6)
C9	0.0395 (9)	0.0160 (7)	0.0184 (7)	0.0049 (6)	0.0045 (6)	0.0006 (6)
C10	0.0303 (8)	0.0162 (7)	0.0219 (7)	−0.0042 (6)	0.0093 (6)	−0.0041 (6)
C11	0.0191 (7)	0.0186 (7)	0.0193 (6)	−0.0010 (6)	0.0042 (5)	−0.0045 (5)
N1	0.0166 (6)	0.0151 (6)	0.0180 (5)	−0.0034 (5)	0.0004 (4)	−0.0011 (4)
N2	0.0150 (5)	0.0169 (6)	0.0162 (5)	−0.0033 (5)	−0.0002 (4)	0.0000 (4)
O1	0.0228 (5)	0.0292 (6)	0.0210 (5)	−0.0091 (5)	−0.0016 (4)	−0.0043 (4)
C12	0.0142 (6)	0.0164 (7)	0.0228 (7)	−0.0012 (5)	−0.0019 (5)	0.0007 (5)
C13	0.0128 (6)	0.0128 (6)	0.0161 (6)	−0.0007 (5)	0.0010 (5)	0.0002 (5)
C14	0.0174 (7)	0.0194 (7)	0.0180 (6)	0.0027 (6)	0.0029 (5)	0.0009 (5)
C15	0.0152 (6)	0.0139 (6)	0.0173 (6)	−0.0012 (5)	0.0005 (5)	0.0005 (5)
C16	0.0130 (6)	0.0123 (6)	0.0157 (6)	−0.0003 (5)	−0.0008 (5)	−0.0016 (5)
C17	0.0141 (6)	0.0147 (6)	0.0141 (6)	−0.0004 (5)	−0.0017 (5)	−0.0011 (5)
C18	0.0146 (7)	0.0243 (7)	0.0216 (7)	0.0044 (6)	0.0026 (5)	0.0007 (6)
C19	0.0245 (7)	0.0214 (7)	0.0171 (7)	0.0008 (6)	0.0062 (5)	0.0010 (5)
C20	0.0213 (7)	0.0147 (6)	0.0128 (6)	0.0009 (5)	0.0007 (5)	−0.0001 (5)
C21	0.0227 (7)	0.0203 (7)	0.0184 (7)	−0.0015 (6)	0.0017 (5)	−0.0003 (5)
C22	0.0382 (9)	0.0179 (7)	0.0242 (7)	−0.0038 (7)	0.0067 (6)	0.0026 (6)
C23	0.0435 (10)	0.0187 (7)	0.0218 (7)	0.0084 (7)	0.0039 (6)	0.0053 (6)
C24	0.0293 (8)	0.0279 (8)	0.0170 (7)	0.0104 (7)	−0.0005 (6)	0.0014 (6)
C25	0.0214 (7)	0.0209 (7)	0.0152 (6)	0.0012 (6)	−0.0006 (5)	0.0000 (5)
C26	0.0141 (6)	0.0138 (6)	0.0133 (6)	0.0003 (5)	0.0019 (5)	−0.0005 (5)
C27	0.0133 (6)	0.0135 (6)	0.0138 (6)	−0.0009 (5)	0.0020 (5)	−0.0007 (5)
C28	0.0129 (6)	0.0146 (6)	0.0140 (6)	−0.0012 (5)	0.0013 (5)	−0.0009 (5)
C29	0.0207 (7)	0.0119 (6)	0.0239 (7)	0.0001 (5)	−0.0048 (5)	−0.0016 (5)
C30	0.0207 (7)	0.0141 (6)	0.0159 (6)	0.0008 (5)	−0.0004 (5)	0.0023 (5)
C31	0.0159 (6)	0.0130 (6)	0.0138 (6)	−0.0021 (5)	−0.0018 (5)	0.0024 (5)
C32	0.0201 (7)	0.0157 (7)	0.0168 (6)	0.0004 (5)	0.0005 (5)	−0.0008 (5)
C33	0.0246 (7)	0.0174 (7)	0.0188 (6)	−0.0026 (6)	−0.0041 (5)	−0.0020 (5)
C34	0.0180 (7)	0.0223 (7)	0.0246 (7)	−0.0043 (6)	−0.0060 (5)	0.0030 (6)
C35	0.0165 (7)	0.0193 (7)	0.0239 (7)	0.0014 (6)	0.0009 (5)	0.0022 (6)
C36	0.0197 (7)	0.0158 (7)	0.0156 (6)	−0.0006 (5)	0.0002 (5)	−0.0005 (5)
N3	0.0116 (5)	0.0184 (6)	0.0162 (5)	0.0011 (4)	0.0017 (4)	0.0012 (4)
N4	0.0110 (5)	0.0175 (6)	0.0196 (6)	0.0004 (4)	0.0003 (4)	0.0025 (5)
N5	0.0162 (5)	0.0095 (5)	0.0154 (5)	−0.0006 (4)	−0.0011 (4)	−0.0007 (4)
N6	0.0154 (6)	0.0100 (5)	0.0170 (5)	−0.0006 (4)	−0.0016 (4)	−0.0012 (4)
O2	0.0123 (5)	0.0237 (5)	0.0287 (5)	0.0033 (4)	0.0038 (4)	0.0073 (4)
O3	0.0193 (5)	0.0114 (5)	0.0236 (5)	−0.0008 (4)	−0.0027 (4)	−0.0009 (4)

C1—C2	1.439 (2)	C19—H19C	0.9800
C2—H2	0.9500	C20—C21	1.393 (2)
C3—C2	1.354 (2)	C20—C25	1.3972 (19)
C3—C4	1.493 (2)	C21—H21	0.9500
C4—H4A	0.9800	C22—C21	1.390 (2)
C4—H4B	0.9800	C22—C23	1.386 (2)
C4—H4C	0.9800	C22—H22	0.9500
C5—H5A	0.9800	C23—H23	0.9500
C5—H5B	0.9800	C24—C23	1.386 (2)
C5—H5C	0.9800	C24—C25	1.390 (2)
C6—C7	1.3909 (19)	C24—H24	0.9500
C7—H7	0.9500	C25—H25	0.9500
C8—C7	1.387 (2)	C27—C26	1.4529 (18)
C8—C9	1.389 (2)	C28—C27	1.3652 (19)
C8—H8	0.9500	C28—C29	1.4982 (18)
C9—H9	0.9500	C29—H29A	0.9800
C10—C9	1.387 (2)	C29—H29B	0.9800
C10—H10	0.9500	C29—H29C	0.9800
C11—C6	1.3966 (19)	C30—H30A	0.9800
C11—C10	1.391 (2)	C30—H30B	0.9800
C11—H11	0.9500	C30—H30C	0.9800
N1—C3	1.3785 (18)	C31—C32	1.3942 (18)
N1—C5	1.4683 (17)	C32—H32	0.9500
N2—C1	1.4018 (17)	C33—C32	1.391 (2)
N2—C6	1.4187 (17)	C33—C34	1.389 (2)
N2—N1	1.4079 (16)	C33—H33	0.9500
O1—C1	1.2342 (17)	C34—H34	0.9500
C12—H12A	0.9800	C35—C34	1.389 (2)
C12—H12B	0.9800	C35—H35	0.9500
C12—H12C	0.9800	C36—C31	1.3908 (19)
C13—C12	1.5388 (18)	C36—C35	1.3877 (19)
C13—C16	1.5318 (17)	C36—H36	0.9500
C13—C27	1.5185 (18)	N3—C17	1.3975 (17)
C14—C13	1.5519 (18)	N3—C19	1.4724 (16)
C14—H14A	0.9800	N4—C15	1.4009 (17)
C14—H14B	0.9800	N4—C20	1.4184 (17)
C14—H14C	0.9800	N4—N3	1.4072 (15)
C15—C16	1.4533 (18)	O2—C15	1.2335 (16)
C17—C16	1.3587 (18)	O3—C26	1.2357 (17)
C17—C18	1.4936 (18)	N5—C28	1.3926 (17)
C18—H18A	0.9800	N5—C30	1.4705 (16)
C18—H18B	0.9800	N5—N6	1.4054 (15)
C18—H18C	0.9800	N6—C26	1.3873 (17)
C19—H19A	0.9800	N6—C31	1.4225 (17)
C19—H19B	0.9800
O1—C1—C2	132.09 (13)	H18B—C18—H18C	109.5
O1—C1—N2	123.27 (13)	H19A—C19—H19B	109.5
N2—C1—C2	104.63 (12)	H19A—C19—H19C	109.5
C3—C2—C1	108.39 (12)	H19B—C19—H19C	109.5
C3—C2—H2	125.8	N3—C19—H19A	109.5
C1—C2—H2	125.8	N3—C19—H19B	109.5
C2—C3—C4	129.21 (13)	N3—C19—H19C	109.5
C2—C3—N1	110.80 (13)	C21—C20—C25	120.07 (13)
N1—C3—C4	119.98 (13)	C21—C20—N4	120.84 (12)
C3—C4—H4A	109.5	C25—C20—N4	119.09 (12)
C3—C4—H4B	109.5	C20—C21—H21	120.3
C3—C4—H4C	109.5	C22—C21—C20	119.30 (14)
H4A—C4—H4B	109.5	C22—C21—H21	120.3
H4A—C4—H4C	109.5	C21—C22—H22	119.4
H4B—C4—H4C	109.5	C23—C22—C21	121.17 (14)
H5A—C5—H5B	109.5	C23—C22—H22	119.4
H5A—C5—H5C	109.5	C22—C23—H23	120.5
H5B—C5—H5C	109.5	C24—C23—C22	119.00 (14)
N1—C5—H5A	109.5	C24—C23—H23	120.5
N1—C5—H5B	109.5	C23—C24—C25	121.01 (14)
N1—C5—H5C	109.5	C23—C24—H24	119.5
C7—C6—C11	120.51 (13)	C25—C24—H24	119.5
C7—C6—N2	120.73 (12)	C20—C25—H25	120.3
C11—C6—N2	118.75 (12)	C24—C25—C20	119.39 (14)
C6—C7—H7	120.2	C24—C25—H25	120.3
C8—C7—C6	119.67 (13)	N6—C26—C27	105.65 (11)
C8—C7—H7	120.2	O3—C26—C27	131.05 (13)
C7—C8—C9	120.20 (14)	O3—C26—N6	123.23 (12)
C7—C8—H8	119.9	C26—C27—C13	120.43 (11)
C9—C8—H8	119.9	C28—C27—C13	132.34 (12)
C8—C9—H9	120.0	C28—C27—C26	107.22 (11)
C10—C9—C8	119.95 (14)	C27—C28—C29	131.96 (12)
C10—C9—H9	120.0	C27—C28—N5	110.67 (11)
C9—C10—C11	120.53 (14)	N5—C28—C29	117.30 (12)
C9—C10—H10	119.7	C28—C29—H29A	109.5
C11—C10—H10	119.7	C28—C29—H29B	109.5
C6—C11—H11	120.5	C28—C29—H29C	109.5
C10—C11—C6	119.07 (13)	H29A—C29—H29B	109.5
C10—C11—H11	120.5	H29A—C29—H29C	109.5
C3—N1—C5	120.26 (12)	H29B—C29—H29C	109.5
C3—N1—N2	105.75 (11)	H30A—C30—H30B	109.5
N2—N1—C5	116.26 (11)	H30A—C30—H30C	109.5
C1—N2—C6	125.95 (12)	H30B—C30—H30C	109.5
C1—N2—N1	109.88 (11)	N5—C30—H30A	109.5
N1—N2—C6	120.01 (11)	N5—C30—H30B	109.5
C13—C12—H12A	109.5	N5—C30—H30C	109.5
C13—C12—H12B	109.5	C32—C31—N6	118.45 (12)
C13—C12—H12C	109.5	C36—C31—C32	120.83 (12)
H12A—C12—H12B	109.5	C36—C31—N6	120.72 (12)
H12A—C12—H12C	109.5	C31—C32—H32	120.5
H12B—C12—H12C	109.5	C33—C32—C31	119.03 (13)
C12—C13—C14	107.43 (11)	C33—C32—H32	120.5
C16—C13—C12	107.15 (10)	C32—C33—H33	119.8
C16—C13—C14	110.26 (11)	C34—C33—C32	120.48 (13)
C27—C13—C12	113.43 (11)	C34—C33—H33	119.8
C27—C13—C14	106.50 (10)	C33—C34—H34	120.1
C27—C13—C16	111.99 (10)	C35—C34—C33	119.89 (13)
C13—C14—H14A	109.5	C35—C34—H34	120.1
C13—C14—H14B	109.5	C34—C35—H35	119.8
C13—C14—H14C	109.5	C36—C35—C34	120.35 (13)
H14A—C14—H14B	109.5	C36—C35—H35	119.8
H14A—C14—H14C	109.5	C31—C36—H36	120.3
H14B—C14—H14C	109.5	C35—C36—C31	119.41 (13)
N4—C15—C16	105.96 (11)	C35—C36—H36	120.3
O2—C15—C16	130.79 (12)	C17—N3—C19	119.52 (11)
O2—C15—N4	123.24 (12)	C17—N3—N4	105.74 (10)
C15—C16—C13	121.04 (11)	N4—N3—C19	114.42 (10)
C17—C16—C13	131.90 (12)	C15—N4—C20	125.25 (11)
C17—C16—C15	106.99 (11)	C15—N4—N3	109.50 (10)
C16—C17—C18	132.34 (13)	N3—N4—C20	119.68 (11)
C16—C17—N3	111.14 (11)	C28—N5—C30	121.43 (11)
N3—C17—C18	116.50 (11)	C28—N5—N6	105.82 (10)
C17—C18—H18A	109.5	N6—N5—C30	113.40 (10)
C17—C18—H18B	109.5	C26—N6—C31	125.14 (11)
C17—C18—H18C	109.5	C26—N6—N5	110.14 (10)
H18A—C18—H18B	109.5	N5—N6—C31	119.77 (10)
H18A—C18—H18C	109.5
N2—C1—C2—C3	−1.74 (15)	C23—C22—C21—C20	−2.3 (2)
O1—C1—C2—C3	177.25 (15)	C21—C22—C23—C24	0.9 (2)
C4—C3—C2—C1	175.98 (14)	C25—C24—C23—C22	1.3 (2)
N1—C3—C2—C1	−3.07 (16)	C23—C24—C25—C20	−2.1 (2)
C11—C6—C7—C8	2.6 (2)	C13—C27—C26—N6	−178.31 (11)
N2—C6—C7—C8	−176.75 (12)	C13—C27—C26—O3	4.7 (2)
C9—C8—C7—C6	−1.5 (2)	C28—C27—C26—N6	1.73 (14)
C7—C8—C9—C10	−0.9 (2)	C28—C27—C26—O3	−175.24 (14)
C11—C10—C9—C8	2.1 (2)	C29—C28—C27—C13	−0.2 (2)
C10—C11—C6—C7	−1.4 (2)	C29—C28—C27—C26	179.77 (13)
C10—C11—C6—N2	177.97 (12)	N5—C28—C27—C13	−177.14 (12)
C6—C11—C10—C9	−1.0 (2)	N5—C28—C27—C26	2.81 (15)
C5—N1—C3—C2	140.75 (13)	C36—C31—C32—C33	0.4 (2)
C5—N1—C3—C4	−38.41 (19)	N6—C31—C32—C33	−179.81 (12)
N2—N1—C3—C2	6.58 (15)	C34—C33—C32—C31	0.0 (2)
N2—N1—C3—C4	−172.58 (12)	C32—C33—C34—C35	−0.3 (2)
C6—N2—C1—C2	162.62 (12)	C36—C35—C34—C33	0.1 (2)
C6—N2—C1—O1	−16.5 (2)	C35—C36—C31—C32	−0.6 (2)
N1—N2—C1—C2	5.83 (14)	C35—C36—C31—N6	179.63 (12)
N1—N2—C1—O1	−173.27 (12)	C31—C36—C35—C34	0.3 (2)
C1—N2—C6—C7	−127.36 (14)	C19—N3—C17—C16	139.18 (12)
C1—N2—C6—C11	53.23 (18)	C19—N3—C17—C18	−39.15 (17)
N1—N2—C6—C7	27.30 (18)	N4—N3—C17—C16	8.40 (14)
N1—N2—C6—C11	−152.11 (12)	N4—N3—C17—C18	−169.93 (11)
C1—N2—N1—C3	−7.69 (14)	C15—N4—C20—C21	−138.74 (14)
C1—N2—N1—C5	−143.99 (12)	C15—N4—C20—C25	41.86 (18)
C6—N2—N1—C3	−166.08 (11)	N3—N4—C20—C21	12.09 (18)
C6—N2—N1—C5	57.62 (16)	N3—N4—C20—C25	−167.32 (11)
C12—C13—C16—C15	−67.73 (15)	C20—N4—C15—C16	157.61 (12)
C12—C13—C16—C17	108.90 (16)	C20—N4—C15—O2	−21.5 (2)
C14—C13—C16—C15	48.90 (16)	N3—N4—C15—C16	4.31 (14)
C14—C13—C16—C17	−134.48 (15)	N3—N4—C15—O2	−174.79 (12)
C27—C13—C16—C15	167.29 (11)	C15—N4—N3—C17	−7.68 (14)
C27—C13—C16—C17	−16.1 (2)	C15—N4—N3—C19	−141.33 (12)
C12—C13—C27—C26	175.73 (11)	C20—N4—N3—C17	−162.70 (11)
C12—C13—C27—C28	−4.3 (2)	C20—N4—N3—C19	63.66 (15)
C14—C13—C27—C26	57.76 (15)	C30—N5—C28—C27	−137.23 (12)
C14—C13—C27—C28	−122.29 (15)	C30—N5—C28—C29	45.31 (17)
C16—C13—C27—C26	−62.84 (15)	N6—N5—C28—C27	−6.17 (14)
C16—C13—C27—C28	117.11 (15)	N6—N5—C28—C29	176.37 (11)
N4—C15—C16—C13	178.23 (11)	C28—N5—N6—C26	7.30 (13)
N4—C15—C16—C17	0.86 (14)	C28—N5—N6—C31	163.66 (11)
O2—C15—C16—C13	−2.8 (2)	C30—N5—N6—C26	142.79 (11)
O2—C15—C16—C17	179.86 (14)	C30—N5—N6—C31	−60.86 (15)
C18—C17—C16—C13	−4.8 (3)	C31—N6—C26—C27	−160.42 (11)
C18—C17—C16—C15	172.16 (14)	C31—N6—C26—O3	16.9 (2)
N3—C17—C16—C13	177.21 (12)	N5—N6—C26—C27	−5.62 (13)
N3—C17—C16—C15	−5.81 (15)	N5—N6—C26—O3	171.66 (12)
C25—C20—C21—C22	1.5 (2)	C26—N6—C31—C32	−57.86 (17)
N4—C20—C21—C22	−177.89 (12)	C26—N6—C31—C36	121.90 (14)
C21—C20—C25—C24	0.7 (2)	N5—N6—C31—C32	149.55 (12)
N4—C20—C25—C24	−179.91 (12)	N5—N6—C31—C36	−30.68 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.95	2.50	3.2949 (17)	142
C5—H5C···O2	0.98	2.44	3.3930 (17)	163
C10—H10···O3ii	0.95	2.53	3.4670 (18)	171
C14—H14A···O3	0.98	2.45	3.1228 (17)	126
C14—H14B···O2	0.98	2.34	3.0275 (17)	126
C21—H21···O1iii	0.95	2.49	3.3428 (18)	150
C25—H25···O2	0.95	2.37	2.8811 (17)	113
C29—H29B···O3iv	0.98	2.38	3.2956 (17)	155
C30—H30A···O3iv	0.98	2.32	3.3015 (16)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.95	2.50	3.2949 (17)	142
C5—H5C⋯O2	0.98	2.44	3.3930 (17)	163
C10—H10⋯O3ii	0.95	2.53	3.4670 (18)	171
C14—H14A⋯O3	0.98	2.45	3.1228 (17)	126
C14—H14B⋯O2	0.98	2.34	3.0275 (17)	126
C21—H21⋯O1iii	0.95	2.49	3.3428 (18)	150
C25—H25⋯O2	0.95	2.37	2.8811 (17)	113
C29—H29B⋯O3iv	0.98	2.38	3.2956 (17)	155
C30—H30A⋯O3iv	0.98	2.32	3.3015 (16)	176

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