Risperidone N-oxide hydrogen peroxide methanol solvate

In the crystal structure of the title compound {systematic name: 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-hydr­oxy-1-[2-(2-meth­yl-4-oxo-3,4,6,7,8,9-hexa­hydro-2H-pyrido[1,2-a]pyrimid­in-3-yl)eth­yl]piperidine N-oxide hydrogen peroxide methanol solvate}, C₂₃H₂₇FN₄O₃·H₂O₂·CH₃OH, the asymmetric unit contains one mol­ecule of risperidone N-oxide, one methanol solvent mol­ecule and one hydrogen peroxide mol­ecule. The piperidine ring adopts a chair conformation, while the tetra­hydro­pyridine ring has a sofa conformation. The hydrogen peroxide mol­ecule links the risperidone mol­ecules to form a chain. O—H...O and C—H...O inter­actions stabilize the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.156
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-hydroxy-1-[2-(2-methyl-4-oxo-3,4,6,7,8,9- hexahydro-2H-pyrido[1,2-a]pyrimidin-3-yl)ethyl]piperidine N-oxide

Crystal data

C23H27FN4O3·H2O2·CH4O	F(000) = 2096
Mr = 492.54	Dx = 1.374 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5217 reflections
a = 37.007 (4) Å	θ = 2.3–27.6°
b = 7.7558 (8) Å	µ = 0.10 mm^−1
c = 17.214 (2) Å	T = 273 K
β = 105.503 (2)°	Block, colorless
V = 4761.0 (9) Å^3	0.20 × 0.15 × 0.10 mm
Z = 8

Data collection

CCD Area Detector diffractometer	3527 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 25.0°, θmin = 1.1°
ω scans	h = −43→43
11481 measured reflections	k = −9→8
4173 independent reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0833P)^2 + 3.9805P] where P = (Fo^2 + 2Fc^2)/3
4173 reflections	(Δ/σ)max < 0.001
319 parameters	Δρmax = 0.55 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.05732 (5)	−0.2528 (3)	0.61966 (11)	0.0854 (5)
N9	0.11080 (5)	−0.0385 (3)	0.34716 (12)	0.0550 (5)
N14	0.24427 (4)	0.0466 (2)	0.36609 (10)	0.0334 (4)
N21	0.39705 (5)	0.0779 (2)	0.55131 (10)	0.0391 (4)
N23	0.41260 (5)	0.1516 (3)	0.43295 (11)	0.0444 (5)
O8	0.07856 (4)	−0.1103 (3)	0.36670 (10)	0.0602 (5)
O26	0.33793 (4)	−0.0069 (2)	0.54912 (10)	0.0558 (5)
O31	0.23610 (4)	−0.08224 (17)	0.30736 (8)	0.0373 (3)
C2	0.07801 (7)	−0.1871 (4)	0.57235 (17)	0.0580 (7)
C3	0.11343 (8)	−0.1259 (4)	0.61081 (16)	0.0619 (7)
H3	0.1218	−0.1282	0.6668	0.074*
C4	0.13623 (7)	−0.0618 (3)	0.56632 (15)	0.0520 (6)
H4	0.1601	−0.0200	0.5911	0.062*
C5	0.12228 (6)	−0.0618 (3)	0.48269 (13)	0.0419 (5)
C6	0.08660 (6)	−0.1225 (3)	0.44779 (14)	0.0473 (5)
C7	0.06290 (7)	−0.1887 (3)	0.49147 (17)	0.0570 (7)
H7	0.0389	−0.2300	0.4673	0.068*
C10	0.13571 (6)	−0.0117 (3)	0.41488 (13)	0.0408 (5)
C11	0.17402 (6)	0.0558 (3)	0.41650 (13)	0.0392 (5)
H11	0.1800	0.1490	0.4563	0.047*
C12	0.17683 (6)	0.1280 (3)	0.33627 (13)	0.0421 (5)
H12A	0.1699	0.0394	0.2952	0.050*
H12B	0.1594	0.2232	0.3206	0.050*
C13	0.21620 (6)	0.1899 (3)	0.34152 (13)	0.0393 (5)
H13A	0.2172	0.2348	0.2895	0.047*
H13B	0.2226	0.2829	0.3805	0.047*
C15	0.24204 (6)	−0.0238 (3)	0.44605 (12)	0.0387 (5)
H15A	0.2494	0.0655	0.4867	0.046*
H15B	0.2596	−0.1185	0.4614	0.046*
C16	0.20317 (6)	−0.0867 (3)	0.44422 (13)	0.0397 (5)
H16A	0.2029	−0.1252	0.4977	0.048*
H16B	0.1968	−0.1843	0.4079	0.048*
C17	0.28291 (6)	0.1173 (3)	0.37267 (14)	0.0411 (5)
H17A	0.2901	0.1916	0.4196	0.049*
H17B	0.2821	0.1873	0.3255	0.049*
C18	0.31266 (6)	−0.0217 (3)	0.37966 (14)	0.0431 (5)
H18A	0.3062	−0.1205	0.4079	0.052*
H18B	0.3130	−0.0591	0.3261	0.052*
C19	0.35113 (6)	0.0426 (3)	0.42420 (13)	0.0387 (5)
C20	0.35987 (6)	0.0343 (3)	0.51026 (13)	0.0393 (5)
C22	0.42157 (6)	0.1366 (3)	0.51068 (13)	0.0390 (5)
C24	0.37724 (6)	0.1046 (3)	0.38878 (13)	0.0430 (5)
C25	0.37055 (8)	0.1255 (5)	0.29964 (15)	0.0727 (9)
H25A	0.3792	0.0245	0.2777	0.109*
H25B	0.3840	0.2246	0.2888	0.109*
H25C	0.3442	0.1408	0.2752	0.109*
C27	0.40726 (7)	0.0559 (3)	0.63976 (13)	0.0503 (6)
H27A	0.3965	−0.0508	0.6526	0.060*
H27B	0.3965	0.1498	0.6634	0.060*
C28	0.44907 (7)	0.0521 (4)	0.67688 (15)	0.0629 (7)
H28A	0.4543	0.0597	0.7351	0.076*
H28B	0.4592	−0.0562	0.6638	0.076*
C29	0.46758 (7)	0.1980 (4)	0.64647 (15)	0.0639 (7)
H29A	0.4943	0.1965	0.6723	0.077*
H29B	0.4575	0.3065	0.6594	0.077*
C30	0.46092 (6)	0.1823 (4)	0.55679 (14)	0.0529 (6)
H30A	0.4777	0.0951	0.5460	0.064*
H30B	0.4675	0.2910	0.5363	0.064*
O32	0.47741 (6)	0.1987 (3)	0.37247 (14)	0.0868 (7)
H32	0.4588	0.1769	0.3880	0.130*
C33	0.47294 (10)	0.3566 (6)	0.3344 (3)	0.1040 (13)
H33A	0.4732	0.4459	0.3732	0.156*
H33B	0.4494	0.3589	0.2938	0.156*
H33C	0.4930	0.3751	0.3099	0.156*
O34	0.27444 (5)	−0.4626 (2)	0.34180 (10)	0.0590 (5)
H34	0.2733	−0.4960	0.2960	0.089*
O35	0.23793 (6)	−0.4112 (2)	0.34625 (13)	0.0659 (5)
H35	0.2348	−0.3086	0.3350	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0750 (11)	0.1013 (14)	0.0928 (12)	−0.0132 (10)	0.0451 (9)	0.0086 (11)
N9	0.0414 (11)	0.0676 (14)	0.0539 (12)	−0.0052 (10)	0.0089 (9)	−0.0025 (10)
N14	0.0352 (9)	0.0251 (9)	0.0381 (9)	−0.0006 (7)	0.0068 (7)	−0.0007 (7)
N21	0.0364 (9)	0.0414 (10)	0.0419 (9)	0.0034 (8)	0.0149 (7)	0.0050 (8)
N23	0.0370 (9)	0.0546 (12)	0.0452 (10)	−0.0040 (8)	0.0170 (8)	0.0054 (8)
O8	0.0390 (9)	0.0776 (13)	0.0588 (10)	−0.0115 (8)	0.0044 (7)	−0.0044 (9)
O26	0.0453 (9)	0.0689 (12)	0.0602 (10)	−0.0067 (8)	0.0261 (8)	0.0089 (9)
O31	0.0447 (8)	0.0256 (7)	0.0403 (8)	−0.0036 (6)	0.0093 (6)	−0.0035 (6)
C2	0.0526 (14)	0.0574 (16)	0.0714 (17)	0.0002 (12)	0.0297 (13)	0.0032 (13)
C3	0.0597 (16)	0.0739 (19)	0.0535 (14)	0.0001 (14)	0.0173 (12)	0.0017 (13)
C4	0.0409 (12)	0.0563 (15)	0.0561 (14)	−0.0013 (11)	0.0084 (10)	−0.0052 (11)
C5	0.0357 (11)	0.0361 (12)	0.0537 (13)	0.0045 (9)	0.0116 (9)	−0.0040 (9)
C6	0.0379 (11)	0.0444 (13)	0.0574 (14)	0.0030 (10)	0.0092 (10)	−0.0037 (10)
C7	0.0393 (12)	0.0553 (16)	0.0783 (18)	−0.0030 (11)	0.0188 (12)	−0.0035 (13)
C10	0.0357 (11)	0.0354 (12)	0.0499 (12)	0.0048 (9)	0.0090 (9)	−0.0038 (9)
C11	0.0356 (11)	0.0358 (12)	0.0449 (11)	0.0029 (9)	0.0086 (9)	−0.0055 (9)
C12	0.0364 (11)	0.0360 (12)	0.0494 (12)	0.0074 (9)	0.0039 (9)	0.0041 (9)
C13	0.0433 (11)	0.0261 (10)	0.0460 (11)	0.0028 (9)	0.0076 (9)	0.0025 (8)
C15	0.0374 (11)	0.0401 (12)	0.0367 (10)	0.0056 (9)	0.0066 (8)	0.0039 (9)
C16	0.0405 (11)	0.0388 (12)	0.0405 (11)	0.0060 (9)	0.0119 (9)	0.0066 (9)
C17	0.0387 (11)	0.0317 (11)	0.0510 (12)	−0.0055 (9)	0.0087 (9)	−0.0018 (9)
C18	0.0380 (11)	0.0372 (12)	0.0558 (13)	−0.0032 (9)	0.0154 (10)	−0.0064 (10)
C19	0.0362 (11)	0.0338 (11)	0.0472 (12)	0.0010 (9)	0.0129 (9)	−0.0013 (9)
C20	0.0345 (11)	0.0345 (12)	0.0528 (12)	0.0029 (9)	0.0181 (9)	0.0029 (9)
C22	0.0354 (11)	0.0389 (12)	0.0451 (12)	0.0024 (9)	0.0149 (9)	0.0034 (9)
C24	0.0386 (11)	0.0478 (13)	0.0441 (12)	−0.0016 (10)	0.0134 (9)	−0.0009 (10)
C25	0.0614 (17)	0.111 (3)	0.0465 (14)	−0.0189 (17)	0.0161 (12)	0.0001 (15)
C27	0.0514 (14)	0.0611 (16)	0.0412 (12)	0.0037 (11)	0.0170 (10)	0.0059 (11)
C28	0.0586 (15)	0.080 (2)	0.0460 (13)	0.0029 (14)	0.0072 (11)	0.0083 (13)
C29	0.0487 (14)	0.082 (2)	0.0555 (15)	−0.0054 (13)	0.0048 (12)	−0.0005 (14)
C30	0.0361 (12)	0.0654 (16)	0.0566 (14)	−0.0041 (11)	0.0113 (10)	0.0074 (12)
O32	0.0565 (12)	0.117 (2)	0.0951 (15)	−0.0005 (12)	0.0348 (11)	0.0176 (14)
C33	0.072 (2)	0.126 (3)	0.115 (3)	−0.004 (2)	0.027 (2)	0.039 (3)
O34	0.0698 (12)	0.0486 (11)	0.0509 (10)	0.0068 (8)	0.0027 (8)	−0.0034 (8)
O35	0.0905 (14)	0.0361 (9)	0.0842 (13)	0.0008 (9)	0.0460 (11)	0.0022 (9)

Geometric parameters (Å, º)

F1—C2	1.357 (3)	C15—H15B	0.9700
N9—C10	1.295 (3)	C16—H16A	0.9700
N9—O8	1.436 (3)	C16—H16B	0.9700
N14—O31	1.396 (2)	C17—C18	1.522 (3)
N14—C13	1.503 (3)	C17—H17A	0.9700
N14—C15	1.503 (3)	C17—H17B	0.9700
N14—C17	1.507 (3)	C18—C19	1.510 (3)
N21—C22	1.364 (3)	C18—H18A	0.9700
N21—C20	1.410 (3)	C18—H18B	0.9700
N21—C27	1.477 (3)	C19—C24	1.361 (3)
N23—C22	1.295 (3)	C19—C20	1.431 (3)
N23—C24	1.375 (3)	C22—C30	1.503 (3)
O8—C6	1.351 (3)	C24—C25	1.496 (3)
O26—C20	1.224 (2)	C25—H25A	0.9600
C2—C7	1.355 (4)	C25—H25B	0.9600
C2—C3	1.385 (4)	C25—H25C	0.9600
C3—C4	1.375 (3)	C27—C28	1.508 (3)
C3—H3	0.9300	C27—H27A	0.9700
C4—C5	1.393 (3)	C27—H27B	0.9700
C4—H4	0.9300	C28—C29	1.489 (4)
C5—C6	1.379 (3)	C28—H28A	0.9700
C5—C10	1.439 (3)	C28—H28B	0.9700
C6—C7	1.396 (3)	C29—C30	1.502 (3)
C7—H7	0.9300	C29—H29A	0.9700
C10—C11	1.505 (3)	C29—H29B	0.9700
C11—C12	1.519 (3)	C30—H30A	0.9700
C11—C16	1.529 (3)	C30—H30B	0.9700
C11—H11	0.9800	O32—C33	1.378 (4)
C12—C13	1.514 (3)	O32—H32	0.8200
C12—H12A	0.9700	C33—H33A	0.9600
C12—H12B	0.9700	C33—H33B	0.9600
C13—H13A	0.9700	C33—H33C	0.9600
C13—H13B	0.9700	O34—O35	1.430 (3)
C15—C16	1.511 (3)	O34—H34	0.8200
C15—H15A	0.9700	O35—H35	0.8200
C10—N9—O8	106.70 (18)	N14—C17—C18	113.56 (17)
O31—N14—C13	109.02 (14)	N14—C17—H17A	108.9
O31—N14—C15	110.43 (14)	C18—C17—H17A	108.9
C13—N14—C15	108.86 (15)	N14—C17—H17B	108.9
O31—N14—C17	109.41 (14)	C18—C17—H17B	108.9
C13—N14—C17	108.81 (15)	H17A—C17—H17B	107.7
C15—N14—C17	110.27 (15)	C19—C18—C17	111.71 (18)
C22—N21—C20	121.14 (17)	C19—C18—H18A	109.3
C22—N21—C27	123.05 (18)	C17—C18—H18A	109.3
C20—N21—C27	115.81 (17)	C19—C18—H18B	109.3
C22—N23—C24	119.40 (18)	C17—C18—H18B	109.3
C6—O8—N9	107.58 (16)	H18A—C18—H18B	107.9
C7—C2—F1	118.0 (2)	C24—C19—C20	119.25 (19)
C7—C2—C3	124.9 (2)	C24—C19—C18	125.1 (2)
F1—C2—C3	117.1 (2)	C20—C19—C18	115.63 (18)
C4—C3—C2	120.1 (2)	O26—C20—N21	119.3 (2)
C4—C3—H3	120.0	O26—C20—C19	125.3 (2)
C2—C3—H3	120.0	N21—C20—C19	115.37 (17)
C3—C4—C5	117.5 (2)	N23—C22—N21	122.55 (19)
C3—C4—H4	121.2	N23—C22—C30	117.98 (18)
C5—C4—H4	121.2	N21—C22—C30	119.45 (19)
C6—C5—C4	119.8 (2)	C19—C24—N23	122.0 (2)
C6—C5—C10	103.70 (19)	C19—C24—C25	123.7 (2)
C4—C5—C10	136.5 (2)	N23—C24—C25	114.25 (19)
O8—C6—C5	110.3 (2)	C24—C25—H25A	109.5
O8—C6—C7	125.9 (2)	C24—C25—H25B	109.5
C5—C6—C7	123.8 (2)	H25A—C25—H25B	109.5
C2—C7—C6	113.8 (2)	C24—C25—H25C	109.5
C2—C7—H7	123.1	H25A—C25—H25C	109.5
C6—C7—H7	123.1	H25B—C25—H25C	109.5
N9—C10—C5	111.7 (2)	N21—C27—C28	112.93 (18)
N9—C10—C11	120.9 (2)	N21—C27—H27A	109.0
C5—C10—C11	127.37 (19)	C28—C27—H27A	109.0
C10—C11—C12	113.86 (17)	N21—C27—H27B	109.0
C10—C11—C16	109.68 (18)	C28—C27—H27B	109.0
C12—C11—C16	109.63 (17)	H27A—C27—H27B	107.8
C10—C11—H11	107.8	C29—C28—C27	110.6 (2)
C12—C11—H11	107.8	C29—C28—H28A	109.5
C16—C11—H11	107.8	C27—C28—H28A	109.5
C13—C12—C11	111.19 (17)	C29—C28—H28B	109.5
C13—C12—H12A	109.4	C27—C28—H28B	109.5
C11—C12—H12A	109.4	H28A—C28—H28B	108.1
C13—C12—H12B	109.4	C28—C29—C30	109.6 (2)
C11—C12—H12B	109.4	C28—C29—H29A	109.8
H12A—C12—H12B	108.0	C30—C29—H29A	109.8
N14—C13—C12	111.33 (16)	C28—C29—H29B	109.8
N14—C13—H13A	109.4	C30—C29—H29B	109.8
C12—C13—H13A	109.4	H29A—C29—H29B	108.2
N14—C13—H13B	109.4	C29—C30—C22	115.57 (19)
C12—C13—H13B	109.4	C29—C30—H30A	108.4
H13A—C13—H13B	108.0	C22—C30—H30A	108.4
N14—C15—C16	112.52 (16)	C29—C30—H30B	108.4
N14—C15—H15A	109.1	C22—C30—H30B	108.4
C16—C15—H15A	109.1	H30A—C30—H30B	107.4
N14—C15—H15B	109.1	C33—O32—H32	109.5
C16—C15—H15B	109.1	O32—C33—H33A	109.5
H15A—C15—H15B	107.8	O32—C33—H33B	109.5
C15—C16—C11	111.18 (18)	H33A—C33—H33B	109.5
C15—C16—H16A	109.4	O32—C33—H33C	109.5
C11—C16—H16A	109.4	H33A—C33—H33C	109.5
C15—C16—H16B	109.4	H33B—C33—H33C	109.5
C11—C16—H16B	109.4	O35—O34—H34	109.5
H16A—C16—H16B	108.0	O34—O35—H35	109.5
C10—N9—O8—C6	−0.1 (3)	C10—C11—C16—C15	179.61 (17)
C7—C2—C3—C4	−0.5 (5)	C12—C11—C16—C15	53.9 (2)
F1—C2—C3—C4	178.3 (2)	O31—N14—C17—C18	−48.7 (2)
C2—C3—C4—C5	−0.1 (4)	C13—N14—C17—C18	−167.74 (17)
C3—C4—C5—C6	0.9 (3)	C15—N14—C17—C18	72.9 (2)
C3—C4—C5—C10	−179.0 (3)	N14—C17—C18—C19	−152.77 (18)
N9—O8—C6—C5	0.3 (3)	C17—C18—C19—C24	−96.5 (3)
N9—O8—C6—C7	−178.9 (2)	C17—C18—C19—C20	84.0 (2)
C4—C5—C6—O8	179.7 (2)	C22—N21—C20—O26	−175.1 (2)
C10—C5—C6—O8	−0.4 (2)	C27—N21—C20—O26	4.8 (3)
C4—C5—C6—C7	−1.1 (4)	C22—N21—C20—C19	5.0 (3)
C10—C5—C6—C7	178.8 (2)	C27—N21—C20—C19	−175.12 (18)
F1—C2—C7—C6	−178.5 (2)	C24—C19—C20—O26	174.4 (2)
C3—C2—C7—C6	0.4 (4)	C18—C19—C20—O26	−6.1 (3)
O8—C6—C7—C2	179.6 (2)	C24—C19—C20—N21	−5.7 (3)
C5—C6—C7—C2	0.5 (4)	C18—C19—C20—N21	173.83 (18)
O8—N9—C10—C5	−0.2 (3)	C24—N23—C22—N21	−0.9 (3)
O8—N9—C10—C11	177.09 (18)	C24—N23—C22—C30	177.6 (2)
C6—C5—C10—N9	0.4 (3)	C20—N21—C22—N23	−1.8 (3)
C4—C5—C10—N9	−179.7 (3)	C27—N21—C22—N23	178.3 (2)
C6—C5—C10—C11	−176.7 (2)	C20—N21—C22—C30	179.8 (2)
C4—C5—C10—C11	3.2 (4)	C27—N21—C22—C30	−0.1 (3)
N9—C10—C11—C12	14.1 (3)	C20—C19—C24—N23	3.4 (3)
C5—C10—C11—C12	−169.1 (2)	C18—C19—C24—N23	−176.0 (2)
N9—C10—C11—C16	−109.2 (2)	C20—C19—C24—C25	−177.5 (2)
C5—C10—C11—C16	67.6 (3)	C18—C19—C24—C25	3.1 (4)
C10—C11—C12—C13	−178.73 (17)	C22—N23—C24—C19	0.0 (3)
C16—C11—C12—C13	−55.4 (2)	C22—N23—C24—C25	−179.1 (2)
O31—N14—C13—C12	62.4 (2)	C22—N21—C27—C28	−17.4 (3)
C15—N14—C13—C12	−58.1 (2)	C20—N21—C27—C28	162.7 (2)
C17—N14—C13—C12	−178.32 (17)	N21—C27—C28—C29	48.4 (3)
C11—C12—C13—N14	58.8 (2)	C27—C28—C29—C30	−61.5 (3)
O31—N14—C15—C16	−62.4 (2)	C28—C29—C30—C22	44.1 (3)
C13—N14—C15—C16	57.2 (2)	N23—C22—C30—C29	167.9 (2)
C17—N14—C15—C16	176.52 (17)	N21—C22—C30—C29	−13.6 (3)
N14—C15—C16—C11	−56.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O32—H32···N23	0.82	2.07	2.882 (3)	173
O34—H34···O31^i	0.82	1.84	2.659 (2)	172
O35—H35···O31	0.82	1.82	2.634 (2)	170
C4—H4···O34^ii	0.93	2.39	3.267 (3)	156
C7—H7···O32^iii	0.93	2.48	3.392 (3)	166
C13—H13B···O35^iv	0.97	2.54	3.192 (3)	124

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, −y−1/2, −z+1; (iii) x−1/2, y−1/2, z; (iv) x, y+1, z.