Paliperidonium nitrate.

In the title mol-ecular salt (systematic name: 3-{2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]eth-yl}-9-hy-droxy-2-methyl-1,6,7,8,9,9a-hexa-hydro-pyrido[1,2-a]pyrimidin-4-one nitrate), C(23)H(29)FN(4)O(3) (+)·NO(3) (-), the piperidine ring displays a chair conformation and its N atom is protonated; the N-H bond is in an axial orientation. The ring bearing the hy-droxy group exhibits a half-chair conformation. The hy-droxy group as well as the adjacent methyl-ene group are disordered over two sets of sites in a 0.823 (5):0.177 (5) ratio. In the crystal, O-H⋯N, O-H⋯O, N-H⋯O and N-H⋯N hydrogen bonds connect the components into a three-dimensional network.

Related literature

For polymorphism of pharmaceutical materials, see: Luo et al. (2012 ▶). For background to the anti-psychotic drug paliperidone, see: Spina & Crupi (2011 ▶).

Experimental

Crystal data

C23H29FN4O3 +·NO3 −

M = 490.51

Monoclinic,

a = 8.3642 (8) Å

b = 22.032 (2) Å

c = 12.4485 (13) Å

β = 92.311 (3)°

V = 2292.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.25 × 0.24 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.968, T max = 0.974

23571 measured reflections

5234 independent reflections

2824 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.178

S = 1.06

5234 reflections

353 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681203841X/hb6895sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203841X/hb6895Isup2.hkl

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

C23H29FN4O3+·NO3−	F(000) = 1036
Mr = 490.51	Dx = 1.421 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 5234 reflections
a = 8.3642 (8) Å	θ = 3.0–27.5°
b = 22.032 (2) Å	µ = 0.11 mm−1
c = 12.4485 (13) Å	T = 293 K
β = 92.311 (3)°	Block, yellow
V = 2292.1 (4) Å3	0.30 × 0.25 × 0.24 mm
Z = 4

Rigaku SCXmini diffractometer	5234 independent reflections
Radiation source: fine-focus sealed tube	2824 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
CCD_Profile_fitting scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −28→28
Tmin = 0.968, Tmax = 0.974	l = −16→16
23571 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0748P)2 + 0.3819P] where P = (Fo2 + 2Fc2)/3
5234 reflections	(Δ/σ)max = 0.003
353 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.45 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	Occ. (<1)
F1	0.0565 (2)	0.98896 (7)	0.73885 (17)	0.0799 (6)
O1	0.2639 (2)	0.84040 (8)	0.50551 (14)	0.0536 (5)
O2	0.2927 (3)	0.47739 (9)	0.97215 (18)	0.0750 (7)
N1	0.2679 (3)	0.77565 (10)	0.51391 (17)	0.0492 (6)
N2	0.3289 (2)	0.57545 (8)	0.67565 (15)	0.0362 (5)
H2	0.4299	0.5821	0.6536	0.043*
N3	0.2952 (2)	0.37405 (9)	0.97199 (16)	0.0424 (5)
N4	0.4064 (3)	0.32060 (9)	0.83226 (17)	0.0457 (5)
H4A	0.4284	0.2865	0.8028	0.055*
C1	0.1967 (3)	0.76100 (11)	0.60118 (18)	0.0375 (6)
C2	0.1398 (3)	0.81375 (11)	0.65504 (19)	0.0367 (6)
C3	0.1871 (3)	0.86150 (12)	0.5923 (2)	0.0432 (6)
C4	0.1608 (3)	0.92174 (12)	0.6162 (2)	0.0517 (7)
H4	0.1951	0.9534	0.5733	0.062*
C5	0.0804 (3)	0.93103 (12)	0.7081 (3)	0.0523 (7)
C6	0.0240 (3)	0.88531 (12)	0.7730 (2)	0.0519 (7)
H6	−0.0335	0.8948	0.8332	0.062*
C7	0.0542 (3)	0.82570 (12)	0.7472 (2)	0.0464 (7)
H7	0.0187	0.7942	0.7898	0.056*
C8	0.2995 (4)	0.61826 (11)	0.76569 (19)	0.0467 (7)
H8A	0.3792	0.6116	0.8232	0.056*
H8B	0.1951	0.6100	0.7937	0.056*
C9	0.3062 (3)	0.68388 (11)	0.72972 (19)	0.0447 (6)
H9A	0.4138	0.6933	0.7087	0.054*
H9B	0.2813	0.7101	0.7894	0.054*
C10	0.1887 (3)	0.69623 (11)	0.63561 (19)	0.0395 (6)
H10	0.0805	0.6884	0.6596	0.047*
C11	0.2218 (4)	0.65205 (12)	0.5461 (2)	0.0507 (7)
H11A	0.1436	0.6581	0.4874	0.061*
H11B	0.3268	0.6604	0.5192	0.061*
C12	0.2153 (4)	0.58721 (12)	0.5825 (2)	0.0523 (7)
H12A	0.1074	0.5777	0.6028	0.063*
H12B	0.2414	0.5608	0.5233	0.063*
C13	0.3179 (3)	0.51047 (11)	0.7099 (2)	0.0441 (6)
H13A	0.3105	0.4851	0.6461	0.053*
H13B	0.2200	0.5051	0.7480	0.053*
C14	0.4572 (3)	0.48869 (11)	0.7812 (2)	0.0474 (7)
H14A	0.5519	0.4846	0.7393	0.057*
H14B	0.4798	0.5179	0.8380	0.057*
C15	0.4152 (3)	0.42850 (10)	0.8288 (2)	0.0382 (6)
C16	0.3326 (3)	0.43048 (11)	0.9267 (2)	0.0446 (6)
C17	0.3373 (3)	0.32160 (11)	0.9231 (2)	0.0402 (6)
C18	0.4442 (3)	0.37363 (11)	0.78350 (19)	0.0392 (6)
C19	0.5206 (4)	0.36680 (13)	0.6777 (2)	0.0557 (7)
H19A	0.4397	0.3679	0.6208	0.084*
H19B	0.5762	0.3287	0.6759	0.084*
H19C	0.5951	0.3994	0.6684	0.084*
C20	0.3052 (4)	0.26146 (13)	0.9775 (3)	0.0589 (8)
H20	0.4009	0.2362	0.9722	0.071*	0.85
H20'	0.1988	0.2505	0.9478	0.071*	0.15
C21	0.2807 (5)	0.2714 (2)	1.0991 (4)	0.0731 (14)	0.823 (5)
H21A	0.2492	0.2335	1.1320	0.088*	0.823 (5)
H21B	0.3801	0.2847	1.1343	0.088*	0.823 (5)
C21'	0.194 (3)	0.2599 (8)	1.0543 (16)	0.059 (5)*	0.177 (5)
H21C	0.2285	0.2300	1.1075	0.071*	0.177 (5)
H21D	0.0947	0.2451	1.0207	0.071*	0.177 (5)
C22	0.1568 (5)	0.31708 (17)	1.1125 (3)	0.0850 (11)
H22A	0.1315	0.3197	1.1877	0.102*
H22B	0.0604	0.3053	1.0718	0.102*
C23	0.2119 (4)	0.37704 (15)	1.0748 (2)	0.0643 (8)
H23A	0.2838	0.3945	1.1295	0.077*
H23B	0.1203	0.4038	1.0658	0.077*
O3	0.1799 (3)	0.23263 (11)	0.9224 (3)	0.0890 (13)	0.823 (5)
H3	0.2103	0.1997	0.9003	0.133*	0.823 (5)
O3'	0.391 (2)	0.2197 (8)	0.9559 (14)	0.118 (7)*	0.177 (5)
H3'	0.4856	0.2297	0.9625	0.177*	0.177 (5)
O4	0.8275 (16)	0.5916 (7)	0.5210 (7)	0.086 (2)	0.69
O5	0.6654 (13)	0.6207 (5)	0.6430 (12)	0.120 (4)	0.69
O6	0.6165 (11)	0.5413 (5)	0.5526 (7)	0.089 (3)	0.69
N5	0.7082 (3)	0.58315 (14)	0.5744 (2)	0.0584 (7)
O4'	0.640 (2)	0.6163 (7)	0.632 (2)	0.069 (5)	0.31
O5'	0.670 (3)	0.5314 (10)	0.565 (2)	0.127 (9)	0.31
O6'	0.837 (4)	0.600 (2)	0.552 (2)	0.176 (14)	0.31

	U11	U22	U33	U12	U13	U23
F1	0.0704 (12)	0.0454 (10)	0.1252 (17)	0.0094 (8)	0.0184 (11)	−0.0060 (10)
O1	0.0679 (13)	0.0498 (12)	0.0440 (11)	−0.0008 (9)	0.0128 (10)	0.0146 (9)
O2	0.1027 (17)	0.0433 (12)	0.0812 (15)	0.0030 (11)	0.0313 (13)	−0.0196 (11)
N1	0.0595 (15)	0.0489 (14)	0.0396 (12)	0.0013 (11)	0.0068 (11)	0.0076 (10)
N2	0.0362 (11)	0.0363 (11)	0.0364 (11)	−0.0011 (9)	0.0041 (9)	0.0015 (9)
N3	0.0479 (13)	0.0439 (13)	0.0359 (11)	−0.0028 (10)	0.0082 (9)	0.0004 (10)
N4	0.0565 (14)	0.0301 (11)	0.0508 (13)	0.0033 (10)	0.0063 (11)	−0.0068 (10)
C1	0.0384 (13)	0.0430 (14)	0.0310 (13)	−0.0021 (11)	−0.0010 (11)	0.0077 (11)
C2	0.0359 (13)	0.0370 (14)	0.0370 (13)	−0.0007 (10)	0.0003 (11)	0.0062 (11)
C3	0.0438 (15)	0.0453 (15)	0.0406 (14)	−0.0006 (12)	0.0017 (12)	0.0115 (12)
C4	0.0480 (16)	0.0374 (15)	0.069 (2)	0.0009 (12)	−0.0005 (15)	0.0176 (14)
C5	0.0422 (15)	0.0370 (15)	0.078 (2)	0.0061 (12)	0.0033 (15)	−0.0002 (14)
C6	0.0444 (16)	0.0525 (17)	0.0595 (18)	0.0051 (13)	0.0114 (14)	−0.0003 (14)
C7	0.0458 (15)	0.0452 (15)	0.0488 (16)	−0.0003 (12)	0.0084 (13)	0.0094 (13)
C8	0.0687 (18)	0.0389 (14)	0.0328 (13)	0.0043 (12)	0.0054 (13)	0.0001 (11)
C9	0.0656 (18)	0.0353 (14)	0.0327 (13)	0.0050 (12)	−0.0034 (12)	−0.0007 (11)
C10	0.0403 (14)	0.0387 (14)	0.0399 (14)	0.0021 (11)	0.0064 (11)	0.0054 (11)
C11	0.0675 (19)	0.0487 (16)	0.0347 (14)	0.0039 (13)	−0.0123 (13)	−0.0008 (12)
C12	0.0672 (19)	0.0433 (16)	0.0447 (16)	0.0039 (13)	−0.0181 (14)	−0.0020 (13)
C13	0.0469 (15)	0.0340 (14)	0.0514 (15)	−0.0026 (11)	0.0013 (13)	0.0051 (12)
C14	0.0425 (15)	0.0415 (15)	0.0582 (17)	−0.0025 (12)	0.0026 (13)	0.0104 (13)
C15	0.0396 (14)	0.0320 (13)	0.0431 (14)	−0.0002 (10)	0.0018 (11)	0.0051 (11)
C16	0.0500 (16)	0.0350 (14)	0.0496 (16)	0.0017 (12)	0.0095 (13)	−0.0043 (12)
C17	0.0397 (14)	0.0341 (14)	0.0467 (15)	0.0001 (11)	−0.0009 (12)	−0.0001 (12)
C18	0.0371 (14)	0.0431 (15)	0.0371 (13)	0.0006 (11)	−0.0014 (11)	0.0027 (12)
C19	0.0607 (18)	0.0643 (19)	0.0429 (15)	0.0016 (14)	0.0127 (14)	−0.0053 (14)
C20	0.0535 (18)	0.0423 (16)	0.081 (2)	0.0009 (14)	0.0059 (17)	0.0162 (15)
C21	0.049 (2)	0.099 (3)	0.071 (3)	−0.004 (2)	−0.004 (2)	0.054 (2)
C22	0.093 (3)	0.097 (3)	0.067 (2)	−0.015 (2)	0.025 (2)	0.022 (2)
C23	0.071 (2)	0.081 (2)	0.0419 (16)	−0.0121 (17)	0.0167 (15)	−0.0057 (15)
O3	0.0617 (19)	0.0486 (16)	0.154 (3)	−0.0114 (12)	−0.0312 (18)	0.0149 (17)
O4	0.048 (4)	0.129 (5)	0.083 (3)	−0.012 (3)	0.028 (2)	0.007 (3)
O5	0.159 (9)	0.103 (6)	0.100 (5)	−0.019 (5)	0.039 (6)	−0.024 (5)
O6	0.070 (3)	0.127 (7)	0.071 (3)	−0.037 (4)	0.016 (2)	−0.016 (3)
N5	0.0556 (19)	0.0624 (19)	0.0579 (17)	0.0019 (16)	0.0097 (15)	0.0076 (14)
O4'	0.042 (5)	0.030 (5)	0.138 (15)	0.005 (4)	0.036 (6)	−0.018 (7)
O5'	0.16 (2)	0.054 (8)	0.167 (17)	−0.032 (12)	0.039 (14)	−0.035 (8)
O6'	0.065 (14)	0.17 (2)	0.30 (4)	0.005 (12)	0.09 (2)	0.06 (3)

F1—C5	1.350 (3)	C13—H13A	0.9700
O1—C3	1.360 (3)	C13—H13B	0.9700
O1—N1	1.431 (3)	C14—C15	1.500 (3)
O2—C16	1.231 (3)	C14—H14A	0.9700
N1—C1	1.301 (3)	C14—H14B	0.9700
N2—C12	1.492 (3)	C15—C18	1.360 (3)
N2—C8	1.493 (3)	C15—C16	1.426 (4)
N2—C13	1.498 (3)	C17—C20	1.517 (4)
N2—H2	0.9108	C18—C19	1.495 (3)
N3—C17	1.359 (3)	C19—H19A	0.9600
N3—C16	1.405 (3)	C19—H19B	0.9600
N3—C23	1.483 (3)	C19—H19C	0.9600
N4—C17	1.291 (3)	C20—O3'	1.204 (17)
N4—C18	1.360 (3)	C20—C21'	1.362 (18)
N4—H4A	0.8594	C20—O3	1.383 (4)
C1—C2	1.433 (3)	C20—C21	1.552 (5)
C1—C10	1.492 (3)	C20—H20	0.9798
C2—C3	1.378 (3)	C20—H20'	0.9803
C2—C7	1.401 (3)	C21—C22	1.459 (5)
C3—C4	1.380 (4)	C21—H21A	0.9700
C4—C5	1.365 (4)	C21—H21B	0.9700
C4—H4	0.9300	C21'—C22	1.492 (18)
C5—C6	1.386 (4)	C21'—H21C	0.9700
C6—C7	1.378 (4)	C21'—H21D	0.9700
C6—H6	0.9300	C22—C23	1.482 (4)
C7—H7	0.9300	C22—H22A	0.9700
C8—C9	1.515 (3)	C22—H22B	0.9700
C8—H8A	0.9700	C23—H23A	0.9700
C8—H8B	0.9700	C23—H23B	0.9700
C9—C10	1.523 (3)	O3—H20'	0.5247
C9—H9A	0.9700	O3—H3	0.8192
C9—H9B	0.9700	O3'—H20	0.4223
C10—C11	1.514 (3)	O3'—H3'	0.8231
C10—H10	0.9800	O4—N5	1.235 (13)
C11—C12	1.500 (3)	O5—N5	1.252 (11)
C11—H11A	0.9700	O6—N5	1.223 (10)
C11—H11B	0.9700	N5—O5'	1.19 (2)
C12—H12A	0.9700	N5—O4'	1.187 (18)
C12—H12B	0.9700	N5—O6'	1.19 (3)
C13—C14	1.513 (3)
C3—O1—N1	107.05 (18)	O2—C16—N3	119.3 (2)
C1—N1—O1	107.3 (2)	O2—C16—C15	124.6 (2)
C12—N2—C8	110.77 (19)	N3—C16—C15	116.0 (2)
C12—N2—C13	110.04 (18)	N4—C17—N3	122.7 (2)
C8—N2—C13	112.10 (18)	N4—C17—C20	118.0 (2)
C12—N2—H2	107.9	N3—C17—C20	119.3 (2)
C8—N2—H2	107.9	C15—C18—N4	122.0 (2)
C13—N2—H2	108.0	C15—C18—C19	123.0 (2)
C17—N3—C16	120.4 (2)	N4—C18—C19	115.0 (2)
C17—N3—C23	124.3 (2)	C18—C19—H19A	109.5
C16—N3—C23	115.3 (2)	C18—C19—H19B	109.5
C17—N4—C18	119.8 (2)	H19A—C19—H19B	109.5
C17—N4—H4A	120.0	C18—C19—H19C	109.5
C18—N4—H4A	120.2	H19A—C19—H19C	109.5
N1—C1—C2	111.2 (2)	H19B—C19—H19C	109.5
N1—C1—C10	120.3 (2)	O3'—C20—C21'	124.6 (12)
C2—C1—C10	128.5 (2)	O3'—C20—O3	89.1 (9)
C3—C2—C7	119.3 (2)	C21'—C20—O3	79.1 (9)
C3—C2—C1	104.2 (2)	O3'—C20—C17	116.7 (9)
C7—C2—C1	136.5 (2)	C21'—C20—C17	118.3 (8)
O1—C3—C2	110.2 (2)	O3—C20—C17	108.9 (3)
O1—C3—C4	125.8 (2)	O3'—C20—C21	115.4 (9)
C2—C3—C4	124.1 (3)	O3—C20—C21	114.9 (3)
C5—C4—C3	114.4 (2)	C17—C20—C21	110.2 (3)
C5—C4—H4	122.8	C21'—C20—H20	128.1
C3—C4—H4	122.8	O3—C20—H20	108.0
F1—C5—C4	117.6 (2)	C17—C20—H20	107.9
F1—C5—C6	117.6 (3)	C21—C20—H20	106.6
C4—C5—C6	124.8 (3)	O3'—C20—H20'	105.5
C7—C6—C5	119.1 (3)	C21'—C20—H20'	67.8
C7—C6—H6	120.4	C17—C20—H20'	102.8
C5—C6—H6	120.4	C21—C20—H20'	104.4
C6—C7—C2	118.3 (2)	H20—C20—H20'	124.4
C6—C7—H7	120.8	C22—C21—C20	109.3 (3)
C2—C7—H7	120.8	C22—C21—H21A	109.8
N2—C8—C9	111.82 (19)	C20—C21—H21A	109.8
N2—C8—H8A	109.3	C22—C21—H21B	109.8
C9—C8—H8A	109.3	C20—C21—H21B	109.8
N2—C8—H8B	109.3	H21A—C21—H21B	108.3
C9—C8—H8B	109.3	C20—C21'—C22	118.7 (13)
H8A—C8—H8B	107.9	C22—C21'—H20'	128.7
C8—C9—C10	111.6 (2)	C20—C21'—H21C	107.6
C8—C9—H9A	109.3	C22—C21'—H21C	107.6
C10—C9—H9A	109.3	H20'—C21'—H21C	123.3
C8—C9—H9B	109.3	C20—C21'—H21D	107.6
C10—C9—H9B	109.3	C22—C21'—H21D	107.6
H9A—C9—H9B	108.0	H20'—C21'—H21D	65.3
C1—C10—C11	113.1 (2)	H21C—C21'—H21D	107.1
C1—C10—C9	110.9 (2)	C21—C22—C23	110.3 (3)
C11—C10—C9	108.7 (2)	C21'—C22—C23	121.7 (7)
C1—C10—H10	108.0	C21—C22—H22A	109.6
C11—C10—H10	108.0	C21'—C22—H22A	125.3
C9—C10—H10	108.0	C23—C22—H22A	109.6
C12—C11—C10	112.3 (2)	C21—C22—H22B	109.6
C12—C11—H11A	109.1	C21'—C22—H22B	72.8
C10—C11—H11A	109.1	C23—C22—H22B	109.6
C12—C11—H11B	109.1	H22A—C22—H22B	108.1
C10—C11—H11B	109.1	C22—C23—N3	113.4 (3)
H11A—C11—H11B	107.9	C22—C23—H23A	108.9
N2—C12—C11	111.7 (2)	N3—C23—H23A	108.9
N2—C12—H12A	109.3	C22—C23—H23B	108.9
C11—C12—H12A	109.3	N3—C23—H23B	108.9
N2—C12—H12B	109.3	H23A—C23—H23B	107.7
C11—C12—H12B	109.3	C20—O3—H3	109.5
H12A—C12—H12B	107.9	H20'—O3—H3	140.8
N2—C13—C14	114.5 (2)	C20—O3'—H20	49.0
N2—C13—H13A	108.6	C20—O3'—H3'	110.7
C14—C13—H13A	108.6	H20—O3'—H3'	63.4
N2—C13—H13B	108.6	O5'—N5—O4'	120.8 (15)
C14—C13—H13B	108.6	O5'—N5—O4	108.4 (14)
H13A—C13—H13B	107.6	O4'—N5—O4	130.7 (12)
C15—C14—C13	109.0 (2)	O4'—N5—O6	106.5 (11)
C15—C14—H14A	109.9	O4—N5—O6	120.5 (8)
C13—C14—H14A	109.9	O5'—N5—O5	127.9 (14)
C15—C14—H14B	109.9	O4—N5—O5	121.8 (9)
C13—C14—H14B	109.9	O6—N5—O5	117.1 (7)
H14A—C14—H14B	108.3	O5'—N5—O6'	122 (2)
C18—C15—C16	118.8 (2)	O4'—N5—O6'	114 (2)
C18—C15—C14	125.0 (2)	O6—N5—O6'	139.3 (18)
C16—C15—C14	116.1 (2)	O5—N5—O6'	103.5 (19)
C3—O1—N1—C1	0.0 (3)	C17—N3—C16—C15	0.0 (3)
O1—N1—C1—C2	0.7 (3)	C23—N3—C16—C15	179.0 (2)
O1—N1—C1—C10	−176.8 (2)	C18—C15—C16—O2	−176.2 (3)
N1—C1—C2—C3	−1.2 (3)	C14—C15—C16—O2	1.2 (4)
C10—C1—C2—C3	176.1 (2)	C18—C15—C16—N3	3.4 (4)
N1—C1—C2—C7	178.0 (3)	C14—C15—C16—N3	−179.2 (2)
C10—C1—C2—C7	−4.7 (5)	C18—N4—C17—N3	2.0 (4)
N1—O1—C3—C2	−0.8 (3)	C18—N4—C17—C20	−176.8 (2)
N1—O1—C3—C4	178.5 (2)	C16—N3—C17—N4	−2.8 (4)
C7—C2—C3—O1	−178.2 (2)	C23—N3—C17—N4	178.3 (2)
C1—C2—C3—O1	1.2 (3)	C16—N3—C17—C20	176.0 (2)
C7—C2—C3—C4	2.5 (4)	C23—N3—C17—C20	−2.8 (4)
C1—C2—C3—C4	−178.1 (2)	C16—C15—C18—N4	−4.4 (4)
O1—C3—C4—C5	179.9 (2)	C14—C15—C18—N4	178.4 (2)
C2—C3—C4—C5	−0.9 (4)	C16—C15—C18—C19	176.1 (2)
C3—C4—C5—F1	177.3 (2)	C14—C15—C18—C19	−1.1 (4)
C3—C4—C5—C6	−1.6 (4)	C17—N4—C18—C15	1.7 (4)
F1—C5—C6—C7	−176.4 (2)	C17—N4—C18—C19	−178.7 (2)
C4—C5—C6—C7	2.4 (4)	N4—C17—C20—O3'	25.3 (10)
C5—C6—C7—C2	−0.7 (4)	N3—C17—C20—O3'	−153.5 (10)
C3—C2—C7—C6	−1.6 (4)	N4—C17—C20—C21'	−161.0 (11)
C1—C2—C7—C6	179.3 (3)	N3—C17—C20—C21'	20.1 (12)
C12—N2—C8—C9	−55.1 (3)	N4—C17—C20—O3	−73.5 (3)
C13—N2—C8—C9	−178.4 (2)	N3—C17—C20—O3	107.6 (3)
N2—C8—C9—C10	56.2 (3)	N4—C17—C20—C21	159.6 (3)
N1—C1—C10—C11	−17.7 (3)	N3—C17—C20—C21	−19.3 (4)
C2—C1—C10—C11	165.2 (2)	O3'—C20—C21—C22	−171.6 (10)
N1—C1—C10—C9	104.7 (3)	C21'—C20—C21—C22	−57.1 (13)
C2—C1—C10—C9	−72.4 (3)	O3—C20—C21—C22	−70.0 (4)
C8—C9—C10—C1	180.0 (2)	C17—C20—C21—C22	53.5 (4)
C8—C9—C10—C11	−55.1 (3)	O3'—C20—C21'—C22	148.9 (15)
C1—C10—C11—C12	179.3 (2)	O3—C20—C21'—C22	−129.9 (17)
C9—C10—C11—C12	55.7 (3)	C17—C20—C21'—C22	−24 (2)
C8—N2—C12—C11	55.1 (3)	C21—C20—C21'—C22	62.1 (14)
C13—N2—C12—C11	179.6 (2)	C20—C21—C22—C21'	49.6 (12)
C10—C11—C12—N2	−56.7 (3)	C20—C21—C22—C23	−66.4 (4)
C12—N2—C13—C14	163.5 (2)	C20—C21'—C22—C21	−69.2 (16)
C8—N2—C13—C14	−72.8 (3)	C20—C21'—C22—C23	13 (2)
N2—C13—C14—C15	167.7 (2)	C21—C22—C23—N3	43.2 (4)
C13—C14—C15—C18	89.9 (3)	C21'—C22—C23—N3	3.9 (12)
C13—C14—C15—C16	−87.4 (3)	C17—N3—C23—C22	−8.4 (4)
C17—N3—C16—O2	179.7 (2)	C16—N3—C23—C22	172.7 (3)
C23—N3—C16—O2	−1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4′	0.91	1.94	2.823 (18)	164
N2—H2···O5	0.91	2.15	3.028 (12)	161
N2—H2···O6	0.91	2.23	2.999 (9)	142
N2—H2···N5	0.91	2.56	3.465 (3)	170
N2—H2···O5′	0.91	2.58	3.36 (3)	144
O3′—H3′···N1i	0.82	2.30	3.117 (18)	169
O3—H3···O5i	0.82	2.11	2.915 (12)	168
O3—H3···O4′i	0.82	2.27	3.064 (19)	163
O3—H3···O6′i	0.82	2.30	2.93 (4)	134
O3—H3···O4i	0.82	2.60	3.187 (16)	130
O3—H3···N5i	0.82	2.67	3.423 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O4′	0.91	1.94	2.823 (18)	164
N2—H2⋯O5	0.91	2.15	3.028 (12)	161
N2—H2⋯O6	0.91	2.23	2.999 (9)	142
N2—H2⋯N5	0.91	2.56	3.465 (3)	170
N2—H2⋯O5′	0.91	2.58	3.36 (3)	144
O3′—H3′⋯N1i	0.82	2.30	3.117 (18)	169
O3—H3⋯O5i	0.82	2.11	2.915 (12)	168
O3—H3⋯O4′i	0.82	2.27	3.064 (19)	163
O3—H3⋯O6′i	0.82	2.30	2.93 (4)	134
O3—H3⋯O4i	0.82	2.60	3.187 (16)	130
O3—H3⋯N5i	0.82	2.67	3.423 (4)	153

Symmetry code: (i) .