5-Acetyl-4-(3-hy-droxy-phen-yl)-6-methyl-1,2,3,4-tetra-hydro-pyrimidin-2-one-tris-(hy-droxy-meth-yl)ammonium chloride (2/1).

The asymmetric unit of the title compound, 2C13H14N2O3·C3H10NO3 (+)·Cl(-), contains two independent mol-ecules (A and B) of the title pyrimidine derivative and one ion-pair of tris-(hy-droxy-meth-yl)ammonium chloride. The pyrimidine ring in each pyrimidine derivative has a half-chair conformation. Its mean plane is inclined to the benzene ring by 87.2 (3)° in mol-ecule A and 85.7 (2)° in mol-ecule B. In the crystal, the pyrimidine derivatives are connected to each other by N-H⋯O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked via O-H-Cl hydrogen bonds, forming corrugated sheets lying parallel to the bc plane. The sheets are linked via C-H⋯O hydrogen bonds, forming a three-dimensional framework. The tris-(hy-droxy-meth-yl)ammonium chloride mol-ecules are located in the cages of the framework. There are also further C-H⋯O hydrogen bonds and C-H⋯π inter-actions present in the three-dimensional framework structure. Both the cation and chloride anion of the tris-(hy-droxy-meth-yl)ammonium chloride ion pair are disordered over two positions, with a refined occupancy ratio of 0.418 (8):0.582 (8) for the cation and 0.71 (4):0.29 (4) for the anion.

Related literature

For the crystal structures of related pyrimidine derivatives, see: NizamMohideen et al. (2008a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

2C13H14N2O3·C3H10NO3 +·Cl−

M = 636.09

Orthorhombic,

a = 15.7317 (7) Å

b = 7.2634 (12) Å

c = 28.8121 (3) Å

V = 3292.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.950, T max = 0.966

27037 measured reflections

5759 independent reflections

4284 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.157

S = 0.88

5759 reflections

489 parameters

270 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030559/su2662sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030559/su2662Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030559/su2662Isup3.cml

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

2C13H14N2O3·C3H10NO3+·Cl−	F(000) = 1344
Mr = 636.09	Dx = 1.283 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5539 reflections
a = 15.7317 (7) Å	θ = 2.3–22.5°
b = 7.2634 (12) Å	µ = 0.17 mm−1
c = 28.8121 (3) Å	T = 293 K
V = 3292.2 (6) Å3	Block, brown
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	5759 independent reflections
Radiation source: fine-focus sealed tube	4284 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω and φ scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −18→18
Tmin = 0.950, Tmax = 0.966	k = −8→8
27037 measured reflections	l = −34→33

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ2(Fo2) + (0.1275P)2] where P = (Fo2 + 2Fc2)/3
5759 reflections	(Δ/σ)max = 0.001
489 parameters	Δρmax = 0.21 e Å−3
270 restraints	Δρmin = −0.23 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
O1	1.1898 (3)	−0.1336 (5)	0.76654 (15)	0.0627 (17)
O2	1.0190 (3)	0.5947 (4)	0.81444 (19)	0.0739 (16)
O3	1.2755 (3)	0.7663 (6)	0.90241 (17)	0.0800 (19)
N1	1.1703 (3)	0.1712 (6)	0.77776 (16)	0.0427 (14)
N2	1.0738 (3)	−0.0308 (5)	0.80570 (14)	0.0394 (14)
C1	1.1482 (3)	−0.0060 (5)	0.78268 (17)	0.0397 (16)
C2	1.0148 (3)	0.1002 (5)	0.81631 (16)	0.0340 (16)
C3	1.0405 (3)	0.2834 (6)	0.81304 (18)	0.0353 (16)
C4	1.1346 (3)	0.3226 (6)	0.80297 (15)	0.0363 (14)
C5	0.9322 (4)	0.0233 (7)	0.8310 (2)	0.0557 (19)
C6	0.9843 (3)	0.4432 (6)	0.8171 (2)	0.0473 (18)
C7	0.8944 (4)	0.4363 (7)	0.8239 (3)	0.080 (3)
C8	1.1811 (3)	0.3670 (5)	0.84776 (16)	0.0330 (14)
C9	1.2002 (4)	0.2298 (7)	0.8808 (2)	0.050 (2)
C10	1.2412 (5)	0.2783 (10)	0.9205 (2)	0.067 (2)
C11	1.2679 (4)	0.4511 (8)	0.92887 (18)	0.0463 (17)
C12	1.2508 (4)	0.5852 (7)	0.89731 (19)	0.0483 (19)
C13	1.2081 (3)	0.5437 (7)	0.8560 (2)	0.0410 (17)
O4	1.3085 (2)	−0.6328 (4)	0.73448 (12)	0.0469 (11)
O5	1.4787 (3)	0.0947 (4)	0.6874 (2)	0.0797 (19)
O6	1.2233 (4)	0.2696 (6)	0.60050 (16)	0.082 (2)
N3	1.4242 (3)	−0.5345 (5)	0.69651 (15)	0.0435 (14)
N4	1.3262 (2)	−0.3263 (6)	0.72435 (15)	0.0380 (14)
C14	1.3476 (3)	−0.4990 (6)	0.71941 (16)	0.0363 (16)
C15	1.3671 (3)	−0.1749 (5)	0.69814 (15)	0.0373 (16)
C16	1.4586 (3)	−0.2193 (5)	0.68982 (18)	0.0337 (16)
C17	1.4817 (3)	−0.3934 (6)	0.68695 (18)	0.0380 (16)
C18	1.5676 (3)	−0.4680 (6)	0.67216 (19)	0.0433 (16)
C19	1.5110 (3)	−0.0543 (6)	0.6852 (2)	0.0417 (14)
C20	1.6079 (3)	−0.0632 (7)	0.6794 (3)	0.063 (2)
C21	1.3158 (3)	−0.1330 (7)	0.65405 (17)	0.0410 (17)
C22	1.2883 (3)	0.0439 (7)	0.6458 (2)	0.0437 (17)
C23	1.2456 (3)	0.0907 (7)	0.60659 (19)	0.0500 (19)
C24	1.2280 (4)	−0.0445 (9)	0.5741 (2)	0.063 (2)
C25	1.2538 (4)	−0.2274 (7)	0.5825 (2)	0.0483 (19)
C26	1.2990 (4)	−0.2677 (8)	0.6224 (2)	0.0523 (19)
O7'	1.0035 (13)	0.728 (2)	0.4720 (8)	0.292 (8)	0.582 (8)
O8'	0.9692 (11)	0.201 (2)	0.4311 (5)	0.196 (6)	0.582 (8)
O9'	0.9596 (13)	0.263 (3)	0.5715 (6)	0.229 (7)	0.582 (8)
N5'	0.9720 (5)	0.4167 (11)	0.4963 (4)	0.089 (3)	0.582 (8)
C27'	0.9651 (9)	0.6189 (16)	0.5113 (6)	0.164 (5)	0.582 (8)
C28'	0.9618 (11)	0.407 (2)	0.4438 (5)	0.155 (6)	0.582 (8)
C29'	0.9145 (11)	0.306 (2)	0.5242 (5)	0.162 (6)	0.582 (8)
O7	1.0080 (11)	0.673 (2)	0.5558 (6)	0.173 (6)	0.418 (8)
O8	0.9161 (16)	0.214 (3)	0.4526 (9)	0.243 (8)	0.418 (8)
O9	1.009 (2)	0.091 (3)	0.5610 (10)	0.293 (9)	0.418 (8)
N5	0.9777 (12)	0.3735 (18)	0.5171 (5)	0.123 (5)	0.418 (8)
C27	0.9570 (12)	0.509 (2)	0.5539 (7)	0.127 (6)	0.418 (8)
C28	0.9308 (18)	0.416 (3)	0.4721 (7)	0.155 (6)	0.418 (8)
C29	0.9450 (17)	0.178 (2)	0.5314 (8)	0.189 (7)	0.418 (8)
Cl1	1.1695 (4)	0.3682 (5)	0.5004 (2)	0.0599 (13)	0.71 (4)
Cl1'	1.1562 (16)	0.335 (4)	0.5030 (8)	0.105 (4)	0.29 (4)
H1A	1.2138 (19)	0.195 (6)	0.7584 (12)	0.0510*
H2A	1.058 (3)	−0.147 (3)	0.8046 (17)	0.0470*
H3	1.30050	0.77880	0.92720	0.0970*
H4	1.13740	0.43170	0.78300	0.0440*
H5A	0.88710	0.10050	0.81980	0.0840*
H5B	0.93000	0.01770	0.86420	0.0840*
H5C	0.92580	−0.09830	0.81840	0.0840*
H7A	0.87180	0.55920	0.82390	0.1210*
H7B	0.88220	0.37850	0.85310	0.1210*
H7C	0.86870	0.36680	0.79930	0.1210*
H9	1.18500	0.10790	0.87550	0.0600*
H10	1.25110	0.18830	0.94280	0.0800*
H11	1.29770	0.47850	0.95590	0.0560*
H13	1.19790	0.63560	0.83430	0.0490*
H3A	1.438 (3)	−0.650 (4)	0.6926 (18)	0.0520*
H4A	1.2747 (15)	−0.298 (6)	0.7333 (12)	0.0460*
H6	1.20900	0.28610	0.57340	0.0980*
H15	1.36510	−0.06470	0.71780	0.0450*
H18A	1.56130	−0.59270	0.66170	0.0650*
H18B	1.60600	−0.46470	0.69810	0.0650*
H18C	1.58990	−0.39370	0.64740	0.0650*
H20A	1.63180	0.05660	0.68470	0.0940*
H20B	1.62150	−0.10330	0.64860	0.0940*
H20C	1.63110	−0.14870	0.70150	0.0940*
H22	1.29940	0.13440	0.66780	0.0520*
H24	1.19930	−0.01480	0.54690	0.0750*
H25	1.24050	−0.32000	0.56140	0.0580*
H26	1.31810	−0.38710	0.62770	0.0630*
H5'	1.02570	0.37890	0.50300	0.1070*	0.582 (8)
H7'	1.05360	0.69870	0.46880	0.4380*	0.582 (8)
H8'	0.93090	0.14330	0.44390	0.2940*	0.582 (8)
H9'	0.96880	0.35990	0.58530	0.3440*	0.582 (8)
H27C	0.90620	0.65340	0.51610	0.1970*	0.582 (8)
H27D	0.99630	0.63980	0.53990	0.1970*	0.582 (8)
H28C	1.00590	0.47770	0.42850	0.1860*	0.582 (8)
H28D	0.90690	0.45520	0.43450	0.1860*	0.582 (8)
H29C	0.90130	0.19160	0.50820	0.1940*	0.582 (8)
H29D	0.86190	0.37180	0.52960	0.1940*	0.582 (8)
H5	1.03480	0.37080	0.51210	0.1480*	0.418 (8)
H7	1.02490	0.69820	0.52970	0.2600*	0.418 (8)
H8	0.89780	0.22040	0.42600	0.3640*	0.418 (8)
H9A	1.02430	0.16360	0.58100	0.4400*	0.418 (8)
H27A	0.89810	0.54520	0.55010	0.1530*	0.418 (8)
H27B	0.96140	0.44670	0.58370	0.1530*	0.418 (8)
H28A	0.96520	0.48940	0.45120	0.1870*	0.418 (8)
H28B	0.87730	0.47860	0.47790	0.1870*	0.418 (8)
H29A	0.89170	0.18930	0.54810	0.2270*	0.418 (8)
H29B	0.93540	0.10410	0.50390	0.2270*	0.418 (8)

	U11	U22	U33	U12	U13	U23
O1	0.061 (3)	0.059 (3)	0.068 (3)	0.0137 (19)	0.012 (2)	−0.020 (2)
O2	0.053 (2)	0.0307 (19)	0.138 (4)	0.0040 (16)	−0.002 (3)	−0.003 (2)
O3	0.107 (4)	0.056 (3)	0.077 (3)	−0.022 (2)	−0.041 (3)	−0.006 (2)
N1	0.040 (2)	0.039 (2)	0.049 (3)	0.0013 (18)	0.0200 (19)	−0.0030 (19)
N2	0.042 (2)	0.0253 (19)	0.051 (3)	−0.0083 (16)	0.007 (2)	0.0034 (18)
C1	0.042 (3)	0.034 (2)	0.043 (3)	−0.001 (2)	0.002 (2)	0.006 (2)
C2	0.042 (3)	0.027 (2)	0.033 (3)	−0.0009 (18)	0.006 (2)	−0.0004 (19)
C3	0.031 (3)	0.033 (2)	0.042 (3)	−0.0068 (18)	0.003 (2)	−0.003 (2)
C4	0.025 (2)	0.040 (2)	0.044 (3)	−0.0119 (18)	0.008 (2)	0.007 (2)
C5	0.042 (3)	0.049 (3)	0.076 (4)	−0.006 (2)	0.012 (3)	0.008 (3)
C6	0.054 (3)	0.021 (2)	0.067 (4)	0.008 (2)	0.007 (3)	0.006 (2)
C7	0.053 (4)	0.040 (3)	0.148 (6)	0.014 (2)	0.004 (4)	−0.035 (3)
C8	0.026 (2)	0.026 (2)	0.047 (3)	0.0025 (16)	0.010 (2)	0.005 (2)
C9	0.056 (4)	0.028 (3)	0.067 (4)	0.006 (2)	−0.008 (3)	0.008 (3)
C10	0.075 (4)	0.077 (4)	0.048 (4)	0.008 (3)	−0.003 (3)	0.009 (3)
C11	0.047 (3)	0.054 (3)	0.038 (3)	−0.004 (2)	−0.004 (2)	−0.004 (3)
C12	0.055 (4)	0.045 (3)	0.045 (3)	0.002 (2)	0.004 (3)	−0.009 (2)
C13	0.040 (3)	0.038 (3)	0.045 (3)	−0.010 (2)	0.004 (2)	0.002 (2)
O4	0.042 (2)	0.0386 (19)	0.060 (2)	−0.0107 (14)	0.0150 (17)	−0.0007 (17)
O5	0.049 (2)	0.0261 (19)	0.164 (5)	0.0039 (16)	0.005 (3)	−0.005 (2)
O6	0.131 (5)	0.055 (3)	0.060 (3)	0.037 (3)	−0.003 (3)	0.002 (2)
N3	0.037 (2)	0.0276 (19)	0.066 (3)	−0.0065 (16)	0.015 (2)	0.002 (2)
N4	0.029 (2)	0.040 (2)	0.045 (3)	0.0097 (16)	0.0058 (17)	−0.0005 (19)
C14	0.028 (2)	0.045 (3)	0.036 (3)	−0.007 (2)	0.009 (2)	0.010 (2)
C15	0.043 (3)	0.021 (2)	0.048 (3)	−0.0082 (18)	0.002 (2)	0.0019 (19)
C16	0.031 (3)	0.026 (2)	0.044 (3)	−0.0033 (17)	0.004 (2)	−0.0038 (19)
C17	0.023 (2)	0.040 (3)	0.051 (3)	0.0007 (17)	0.003 (2)	−0.001 (2)
C18	0.037 (3)	0.030 (2)	0.063 (3)	0.0072 (19)	0.013 (3)	0.001 (2)
C19	0.024 (2)	0.042 (2)	0.059 (3)	0.0027 (19)	−0.007 (2)	0.015 (2)
C20	0.026 (3)	0.055 (3)	0.108 (5)	−0.003 (2)	0.006 (3)	−0.012 (3)
C21	0.029 (3)	0.050 (3)	0.044 (3)	0.002 (2)	0.005 (2)	0.001 (2)
C22	0.046 (3)	0.038 (3)	0.047 (3)	−0.001 (2)	0.002 (2)	−0.004 (2)
C23	0.044 (3)	0.051 (3)	0.055 (4)	0.019 (2)	0.003 (3)	−0.002 (2)
C24	0.057 (4)	0.068 (4)	0.063 (4)	0.002 (3)	0.000 (3)	0.003 (3)
C25	0.053 (3)	0.038 (3)	0.054 (4)	−0.004 (2)	−0.005 (3)	−0.012 (2)
C26	0.057 (4)	0.049 (3)	0.051 (3)	0.014 (2)	0.006 (3)	−0.001 (3)
O7'	0.300 (15)	0.273 (14)	0.303 (15)	0.041 (11)	0.023 (11)	0.032 (11)
O8'	0.179 (10)	0.264 (11)	0.144 (9)	0.084 (9)	−0.033 (8)	−0.031 (8)
O9'	0.216 (12)	0.293 (13)	0.179 (10)	0.038 (11)	0.014 (9)	0.013 (10)
N5'	0.052 (3)	0.122 (5)	0.094 (7)	0.026 (4)	−0.013 (5)	0.019 (6)
C27'	0.145 (8)	0.169 (9)	0.177 (11)	0.073 (7)	−0.024 (8)	−0.055 (8)
C28'	0.123 (9)	0.208 (11)	0.135 (10)	0.047 (9)	−0.058 (8)	0.033 (9)
C29'	0.149 (10)	0.202 (12)	0.134 (8)	−0.014 (9)	0.049 (7)	−0.004 (9)
O7	0.172 (11)	0.180 (10)	0.168 (11)	0.049 (9)	0.016 (9)	−0.031 (9)
O8	0.220 (14)	0.271 (14)	0.237 (15)	0.031 (12)	−0.010 (12)	0.036 (12)
O9	0.290 (16)	0.301 (16)	0.289 (16)	0.052 (13)	0.012 (13)	−0.013 (13)
N5	0.117 (8)	0.156 (8)	0.097 (8)	−0.018 (7)	−0.001 (7)	0.011 (7)
C27	0.106 (9)	0.138 (10)	0.138 (10)	0.006 (8)	0.033 (8)	−0.028 (8)
C28	0.123 (11)	0.207 (11)	0.136 (11)	0.022 (10)	−0.025 (10)	0.021 (10)
C29	0.190 (12)	0.213 (12)	0.164 (11)	−0.001 (10)	−0.001 (10)	−0.021 (10)
Cl1	0.075 (2)	0.063 (3)	0.0417 (17)	0.0184 (10)	0.0047 (18)	0.0032 (18)
Cl1'	0.062 (4)	0.174 (9)	0.080 (5)	0.046 (6)	0.023 (6)	0.036 (7)

O1—C1	1.226 (6)	C10—C11	1.345 (9)
O2—C6	1.231 (6)	C11—C12	1.359 (8)
O3—C12	1.379 (7)	C12—C13	1.400 (8)
O3—H3	0.8200	C4—H4	0.9800
O4—C14	1.229 (5)	C5—H5C	0.9600
O5—C19	1.197 (6)	C5—H5A	0.9600
O6—C23	1.357 (7)	C5—H5B	0.9600
O6—H6	0.8200	C7—H7B	0.9600
O7'—C27'	1.51 (3)	C7—H7C	0.9600
O8'—C28'	1.55 (2)	C7—H7A	0.9600
O9'—C29'	1.57 (2)	C9—H9	0.9300
O7'—H7'	0.8200	C10—H10	0.9300
O8'—H8'	0.8200	C11—H11	0.9300
O9'—H9'	0.8200	C13—H13	0.9300
O7—C27	1.44 (2)	C15—C16	1.495 (7)
O8—C28	1.59 (3)	C15—C21	1.536 (7)
O9—C29	1.46 (4)	C16—C17	1.318 (6)
O7—H7	0.8200	C16—C19	1.461 (6)
O8—H8	0.8200	C17—C18	1.517 (7)
O9—H9A	0.8200	C19—C20	1.535 (7)
N1—C4	1.433 (6)	C21—C26	1.363 (8)
N1—C1	1.341 (6)	C21—C22	1.377 (7)
N2—C1	1.357 (7)	C22—C23	1.358 (8)
N2—C2	1.364 (6)	C23—C24	1.385 (8)
N1—H1A	0.90 (3)	C24—C25	1.410 (8)
N2—H2A	0.88 (2)	C25—C26	1.383 (8)
N3—C14	1.398 (7)	C15—H15	0.9800
N3—C17	1.394 (6)	C18—H18C	0.9600
N4—C15	1.481 (6)	C18—H18A	0.9600
N4—C14	1.307 (6)	C18—H18B	0.9600
N3—H3A	0.87 (3)	C20—H20B	0.9600
N4—H4A	0.88 (3)	C20—H20A	0.9600
N5'—C27'	1.535 (15)	C20—H20C	0.9600
N5'—C29'	1.453 (18)	C22—H22	0.9300
N5'—C28'	1.523 (18)	C24—H24	0.9300
N5'—H5'	0.9100	C25—H25	0.9300
N5—C28	1.52 (3)	C26—H26	0.9300
N5—C27	1.48 (2)	C27'—H27C	0.9700
N5—C29	1.57 (2)	C27'—H27D	0.9700
N5—H5	0.9100	C28'—H28C	0.9700
C2—C5	1.476 (8)	C28'—H28D	0.9700
C2—C3	1.394 (6)	C29'—H29C	0.9700
C3—C6	1.464 (6)	C29'—H29D	0.9700
C3—C4	1.535 (7)	C27—H27A	0.9700
C4—C8	1.518 (6)	C27—H27B	0.9700
C6—C7	1.429 (8)	C28—H28A	0.9700
C8—C9	1.411 (7)	C28—H28B	0.9700
C8—C13	1.373 (6)	C29—H29A	0.9700
C9—C10	1.360 (9)	C29—H29B	0.9700
C12—O3—H3	109.00	N3—C14—N4	116.8 (4)
C23—O6—H6	109.00	C16—C15—C21	114.6 (4)
C27'—O7'—H7'	109.00	N4—C15—C21	109.9 (4)
C28'—O8'—H8'	109.00	N4—C15—C16	109.9 (3)
C29'—O9'—H9'	109.00	C17—C16—C19	128.7 (4)
C27—O7—H7	109.00	C15—C16—C17	118.9 (4)
C28—O8—H8	109.00	C15—C16—C19	112.4 (3)
C29—O9—H9A	110.00	C16—C17—C18	127.3 (4)
C1—N1—C4	125.6 (4)	N3—C17—C18	111.8 (4)
C1—N2—C2	127.1 (4)	N3—C17—C16	120.9 (4)
C1—N1—H1A	117 (3)	O5—C19—C16	119.8 (5)
C4—N1—H1A	118 (3)	O5—C19—C20	117.7 (4)
C1—N2—H2A	111 (3)	C16—C19—C20	122.4 (4)
C2—N2—H2A	119 (3)	C15—C21—C22	119.5 (4)
C14—N3—C17	121.1 (4)	C22—C21—C26	119.6 (5)
C14—N4—C15	123.1 (4)	C15—C21—C26	120.9 (4)
C14—N3—H3A	117 (3)	C21—C22—C23	122.2 (5)
C17—N3—H3A	121 (3)	C22—C23—C24	118.9 (5)
C15—N4—H4A	112 (3)	O6—C23—C24	122.7 (5)
C14—N4—H4A	120 (3)	O6—C23—C22	118.4 (5)
C28'—N5'—C29'	117.3 (10)	C23—C24—C25	119.6 (5)
C27'—N5'—C29'	109.3 (10)	C24—C25—C26	119.3 (5)
C27'—N5'—C28'	108.5 (10)	C21—C26—C25	120.3 (5)
C27'—N5'—H5'	107.00	C16—C15—H15	107.00
C29'—N5'—H5'	107.00	C21—C15—H15	107.00
C28'—N5'—H5'	107.00	N4—C15—H15	107.00
C27—N5—C28	111.6 (15)	H18A—C18—H18C	110.00
C27—N5—C29	110.0 (14)	C17—C18—H18C	109.00
C28—N5—C29	104.4 (16)	H18A—C18—H18B	109.00
C29—N5—H5	110.00	C17—C18—H18B	109.00
C28—N5—H5	110.00	C17—C18—H18A	109.00
C27—N5—H5	110.00	H18B—C18—H18C	109.00
O1—C1—N2	123.0 (4)	H20B—C20—H20C	109.00
O1—C1—N1	123.2 (5)	C19—C20—H20B	110.00
N1—C1—N2	113.8 (4)	H20A—C20—H20C	109.00
N2—C2—C5	113.5 (4)	C19—C20—H20C	109.00
C3—C2—C5	129.5 (4)	C19—C20—H20A	109.00
N2—C2—C3	117.0 (4)	H20A—C20—H20B	110.00
C2—C3—C6	125.2 (4)	C23—C22—H22	119.00
C4—C3—C6	116.8 (4)	C21—C22—H22	119.00
C2—C3—C4	118.0 (4)	C25—C24—H24	120.00
N1—C4—C3	109.4 (4)	C23—C24—H24	120.00
N1—C4—C8	113.9 (4)	C26—C25—H25	120.00
C3—C4—C8	110.1 (4)	C24—C25—H25	120.00
C3—C6—C7	125.5 (4)	C21—C26—H26	120.00
O2—C6—C3	115.9 (4)	C25—C26—H26	120.00
O2—C6—C7	118.6 (4)	O7'—C27'—N5'	105.3 (12)
C4—C8—C13	119.7 (4)	O8'—C28'—N5'	105.8 (11)
C9—C8—C13	118.6 (5)	O9'—C29'—N5'	108.0 (13)
C4—C8—C9	121.8 (4)	H27C—C27'—H27D	109.00
C8—C9—C10	119.1 (5)	N5'—C27'—H27D	111.00
C9—C10—C11	122.7 (6)	N5'—C27'—H27C	111.00
C10—C11—C12	119.1 (5)	O7'—C27'—H27C	111.00
O3—C12—C11	123.8 (5)	O7'—C27'—H27D	111.00
C11—C12—C13	120.6 (5)	O8'—C28'—H28C	111.00
O3—C12—C13	115.5 (5)	H28C—C28'—H28D	109.00
C8—C13—C12	119.8 (5)	N5'—C28'—H28C	111.00
N1—C4—H4	108.00	O8'—C28'—H28D	111.00
C8—C4—H4	108.00	N5'—C28'—H28D	111.00
C3—C4—H4	108.00	N5'—C29'—H29C	110.00
C2—C5—H5C	109.00	N5'—C29'—H29D	110.00
H5A—C5—H5C	109.00	O9'—C29'—H29C	110.00
C2—C5—H5B	110.00	O9'—C29'—H29D	110.00
C2—C5—H5A	109.00	H29C—C29'—H29D	108.00
H5A—C5—H5B	109.00	O7—C27—N5	117.1 (16)
H5B—C5—H5C	110.00	O8—C28—N5	100.6 (16)
H7A—C7—H7B	109.00	O9—C29—N5	108.6 (19)
C6—C7—H7B	109.00	O7—C27—H27A	108.00
H7B—C7—H7C	109.00	O7—C27—H27B	108.00
C6—C7—H7C	110.00	N5—C27—H27A	108.00
C6—C7—H7A	109.00	N5—C27—H27B	108.00
H7A—C7—H7C	109.00	H27A—C27—H27B	107.00
C8—C9—H9	120.00	O8—C28—H28A	112.00
C10—C9—H9	120.00	O8—C28—H28B	112.00
C9—C10—H10	119.00	N5—C28—H28A	112.00
C11—C10—H10	119.00	N5—C28—H28B	112.00
C10—C11—H11	120.00	H28A—C28—H28B	109.00
C12—C11—H11	120.00	O9—C29—H29A	110.00
C12—C13—H13	120.00	O9—C29—H29B	110.00
C8—C13—H13	120.00	N5—C29—H29A	110.00
O4—C14—N3	116.9 (4)	N5—C29—H29B	110.00
O4—C14—N4	126.3 (4)	H29A—C29—H29B	109.00
C4—N1—C1—O1	−167.0 (5)	C3—C4—C8—C13	−109.3 (5)
C4—N1—C1—N2	15.3 (7)	C4—C8—C9—C10	−179.3 (5)
C1—N1—C4—C3	−33.4 (6)	C9—C8—C13—C12	−2.3 (8)
C1—N1—C4—C8	90.3 (6)	C4—C8—C13—C12	179.8 (5)
C2—N2—C1—O1	−165.3 (5)	C13—C8—C9—C10	2.9 (8)
C1—N2—C2—C5	165.7 (5)	C8—C9—C10—C11	−3.0 (10)
C1—N2—C2—C3	−15.8 (7)	C9—C10—C11—C12	2.5 (11)
C2—N2—C1—N1	12.4 (7)	C10—C11—C12—C13	−1.8 (9)
C14—N3—C17—C16	−14.9 (7)	C10—C11—C12—O3	−179.8 (6)
C17—N3—C14—N4	11.1 (7)	C11—C12—C13—C8	1.8 (8)
C17—N3—C14—O4	−166.2 (4)	O3—C12—C13—C8	179.9 (5)
C14—N3—C17—C18	167.0 (4)	N4—C15—C21—C22	125.6 (5)
C14—N4—C15—C21	93.6 (5)	N4—C15—C21—C26	−56.0 (6)
C14—N4—C15—C16	−33.4 (6)	C21—C15—C16—C19	83.2 (5)
C15—N4—C14—O4	−168.3 (4)	C21—C15—C16—C17	−95.9 (5)
C15—N4—C14—N3	14.6 (6)	N4—C15—C16—C19	−152.5 (4)
C27'—N5'—C29'—O9'	−82.1 (14)	C16—C15—C21—C22	−110.1 (5)
C27'—N5'—C28'—O8'	−179.9 (11)	C16—C15—C21—C26	68.3 (6)
C29'—N5'—C27'—O7'	−162.5 (13)	N4—C15—C16—C17	28.4 (6)
C28'—N5'—C29'—O9'	154.1 (12)	C15—C16—C19—O5	−1.3 (8)
C29'—N5'—C28'—O8'	−55.6 (16)	C15—C16—C17—C18	170.8 (5)
C28'—N5'—C27'—O7'	−33.6 (15)	C15—C16—C17—N3	−7.0 (8)
C5—C2—C3—C6	−10.1 (9)	C17—C16—C19—O5	177.7 (6)
C5—C2—C3—C4	171.8 (5)	C17—C16—C19—C20	−4.8 (9)
N2—C2—C3—C6	171.7 (5)	C15—C16—C19—C20	176.3 (5)
N2—C2—C3—C4	−6.4 (7)	C19—C16—C17—C18	−8.2 (9)
C2—C3—C6—C7	−1.6 (9)	C19—C16—C17—N3	174.1 (5)
C2—C3—C6—O2	178.2 (5)	C15—C21—C26—C25	−179.0 (5)
C4—C3—C6—C7	176.5 (6)	C26—C21—C22—C23	−1.0 (8)
C4—C3—C6—O2	−3.7 (7)	C15—C21—C22—C23	177.4 (5)
C6—C3—C4—N1	−151.0 (4)	C22—C21—C26—C25	−0.7 (8)
C6—C3—C4—C8	83.2 (5)	C21—C22—C23—C24	1.0 (8)
C2—C3—C4—N1	27.3 (6)	C21—C22—C23—O6	−177.8 (5)
C2—C3—C4—C8	−98.6 (5)	O6—C23—C24—C25	179.4 (6)
N1—C4—C8—C9	−50.3 (6)	C22—C23—C24—C25	0.7 (8)
N1—C4—C8—C13	127.5 (5)	C23—C24—C25—C26	−2.3 (9)
C3—C4—C8—C9	73.0 (6)	C24—C25—C26—C21	2.3 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4i	0.90 (3)	2.06 (4)	2.882 (6)	151 (4)
N2—H2A···O2ii	0.88 (2)	1.99 (3)	2.865 (5)	170 (5)
O3—H3···Cl1iii	0.82	2.26	3.044 (8)	161
N3—H3A···O5ii	0.87 (3)	1.97 (3)	2.839 (5)	175 (3)
N4—H4A···O1	0.88 (3)	2.03 (3)	2.836 (6)	152 (3)
O6—H6···Cl1	0.82	2.27	3.090 (7)	173
C13—H13···O1i	0.93	2.58	3.496 (7)	171
C18—H18B···O1iv	0.96	2.48	3.411 (7)	164
C22—H22···O4i	0.93	2.56	3.485 (6)	171
C28′—H28D···Cg1v	0.97	2.65	3.598 (17)	166
C27—H27A···Cg2vi	0.97	2.73	3.444 (19)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C13 and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.90 (3)	2.06 (4)	2.882 (6)	151 (4)
N2—H2A⋯O2ii	0.88 (2)	1.99 (3)	2.865 (5)	170 (5)
O3—H3⋯Cl1iii	0.82	2.26	3.044 (8)	161
N3—H3A⋯O5ii	0.87 (3)	1.97 (3)	2.839 (5)	175 (3)
N4—H4A⋯O1	0.88 (3)	2.03 (3)	2.836 (6)	152 (3)
O6—H6⋯Cl1	0.82	2.27	3.090 (7)	173
C13—H13⋯O1i	0.93	2.58	3.496 (7)	171
C18—H18B⋯O1iv	0.96	2.48	3.411 (7)	164
C22—H22⋯O4i	0.93	2.56	3.485 (6)	171
C28′—H28D⋯Cg1v	0.97	2.65	3.598 (17)	166
C27—H27A⋯Cg2vi	0.97	2.73	3.444 (19)	131

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