Risperidone chloride 2.5-hydrate: a new crystalline form

Wang, D.-H.; Pan, Y.-J.

doi:10.1107/S1600536806002157

Risperidone chloride 2.5-hydrate: a new crystalline form

The asymmetric unit of the title compound, C₂₃H₂₈FN₄O₂⁺·Cl⁻·2.5H₂O, contain one risperidone cation {systematic name: 4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-[2-(2-methyl-4-oxo-3,4,6,7,8,9-hexahydro-2H-pyrido[1,2-a]pyrimidin-3-yl)ethyl]piperidinium}, one Cl⁻ anion, and two and a half water molecules. The piperidine ring adopts a chair conformation, while the tetrahydropyridine ring has a sofa conformation. Each Cl⁻ anion and the water molecules are linked to the risperidone molecules via O—H

O, O—H

N, O—H

Cl and N—H

Cl hydrogen bonds which stabilize the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002157/at6075sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002157/at6075Isup2.hkl Contains datablock I

CCDC reference: 298364

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
Disorder in solvent or counterion
R factor = 0.041
wR factor = 0.101
Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      12.00 Perc.

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

   3 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

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: Crystal Structure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: Crystal Structure.

4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-[2-(2-methyl-4-oxo-3,4,6,7,8,9- hexahydro-2H-pyrido[1,2-a]pyrimidin-3-yl)ethyl]piperidinium chloride 2.5-hydrate top

Crystal data top

C₂₃H₂₈FN₄O₂⁺·Cl⁻·2.5H₂O	F(000) = 1044.00
M_r = 491.99	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 19056 reflections
a = 10.027 (3) Å	θ = 3.0–27.5°
b = 18.431 (4) Å	µ = 0.20 mm⁻¹
c = 13.394 (4) Å	T = 298 K
β = 100.613 (11)°	Block, brown
V = 2433.0 (11) Å³	0.30 × 0.26 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3581 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.031
ω scans	θ_max = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→12
T_min = 0.913, T_max = 0.960	k = −23→23
23832 measured reflections	l = −17→17
5562 independent reflections

Refinement top

Refinement on F²	w = 1/[0.0005F_o² + 1σ(F_o²)]/(4F_o²)
R[F² > 2σ(F²)] = 0.041	(Δ/σ)_max < 0.001
wR(F²) = 0.102	Δρ_max = 0.51 e Å⁻³
S = 1.04	Δρ_min = −0.33 e Å⁻³
5562 reflections	Extinction correction: Larson (1970)
308 parameters	Extinction coefficient: 99 (21)
H-atom parameters constrained

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.46396 (4)	0.41240 (2)	0.66523 (4)	0.05455 (13)
F1	0.02999 (12)	0.69441 (6)	0.76030 (10)	0.0766 (4)
O1	0.47576 (12)	0.78289 (6)	0.75840 (10)	0.0535 (3)
O2	1.03858 (12)	0.36035 (6)	0.49888 (10)	0.0539 (3)
O3	0.16081 (13)	0.44177 (6)	0.67188 (12)	0.0752 (4)
O4	0.1315 (2)	0.43621 (9)	0.88382 (14)	0.1169 (7)
O5	0.0347 (4)	0.5558 (2)	0.9741 (3)	0.1377 (18)	0.50
N1	0.74081 (12)	0.47731 (6)	0.66009 (9)	0.0328 (3)
N2	0.59673 (14)	0.74596 (6)	0.74586 (12)	0.0491 (4)
N3	1.01137 (13)	0.23864 (6)	0.47595 (10)	0.0396 (3)
N4	0.80844 (14)	0.18132 (6)	0.49170 (11)	0.0433 (4)
C1	0.67478 (16)	0.62490 (8)	0.71696 (12)	0.0387 (4)
C2	0.63629 (17)	0.59535 (8)	0.60874 (12)	0.0408 (4)
C3	0.73354 (17)	0.53766 (8)	0.58494 (12)	0.0406 (4)
C4	0.79240 (16)	0.50553 (8)	0.76470 (12)	0.0399 (4)
C5	0.69638 (17)	0.56216 (8)	0.79342 (12)	0.0400 (4)
C6	0.56730 (17)	0.67718 (6)	0.73657 (12)	0.0383 (4)
C7	0.42758 (17)	0.66399 (8)	0.74123 (12)	0.0383 (4)
C8	0.34043 (17)	0.60384 (8)	0.73419 (12)	0.0449 (4)
C9	0.20728 (18)	0.61562 (10)	0.74066 (13)	0.0515 (5)
C10	0.16310 (19)	0.68616 (10)	0.75505 (13)	0.0527 (5)
C11	0.24287 (19)	0.74639 (9)	0.76278 (12)	0.0505 (5)
C12	0.37643 (18)	0.73260 (8)	0.75525 (12)	0.0431 (4)
C13	0.81998 (16)	0.41241 (8)	0.63667 (12)	0.0414 (4)
C14	0.77004 (18)	0.38422 (8)	0.52978 (12)	0.0443 (4)
C15	0.82572 (17)	0.31013 (8)	0.51264 (12)	0.0385 (4)
C16	0.96252 (17)	0.30763 (8)	0.49650 (12)	0.0398 (4)
C17	1.15257 (18)	0.23649 (9)	0.45730 (14)	0.0517 (5)
C18	1.1889 (2)	0.16528 (11)	0.41497 (19)	0.0734 (7)
C19	1.1395 (2)	0.10295 (11)	0.46773 (19)	0.0730 (7)
C20	0.9888 (2)	0.10563 (9)	0.45534 (16)	0.0593 (6)
C21	0.93185 (18)	0.17862 (8)	0.47537 (12)	0.0414 (4)
C22	0.75375 (17)	0.24736 (8)	0.51052 (12)	0.0410 (4)
C23	0.6117 (2)	0.24280 (10)	0.53038 (17)	0.0593 (6)
H1	0.7605	0.6515	0.7224	0.046*
H411	0.1321	0.4318	0.8111	0.142*
H412	0.1861	0.3978	0.9181	0.142*
H8	0.3721	0.5573	0.7254	0.053*
H9	0.1468	0.5770	0.7355	0.062*
H11	0.2105	0.7927	0.7723	0.060*
H21	0.5461	0.5745	0.6002	0.048*
H22	0.6360	0.6352	0.5615	0.049*
H31	0.7017	0.5189	0.5171	0.049*
H32	0.8230	0.5587	0.5887	0.049*
H41	0.8810	0.5273	0.7669	0.047*
H42	0.8000	0.4657	0.8127	0.047*
H51	0.7342	0.5813	0.8601	0.048*
H52	0.6096	0.5395	0.7953	0.047*
H111	0.6619	0.4594	0.6620	0.040*
H131	0.9147	0.4259	0.6434	0.050*
H132	0.8111	0.3742	0.6848	0.050*
H141	0.7977	0.4179	0.4818	0.053*
H142	0.6718	0.3814	0.5181	0.053*
H171	1.2140	0.2452	0.5211	0.063*
H172	1.1633	0.2746	0.4094	0.063*
H181	1.2869	0.1621	0.4227	0.091*
H182	1.1486	0.1631	0.3434	0.092*
H191	1.1791	0.1050	0.5394	0.090*
H192	1.1661	0.0581	0.4390	0.089*
H201	0.9612	0.0710	0.5021	0.074*
H202	0.9507	0.0917	0.3861	0.074*
H231	0.5988	0.1969	0.5611	0.073*
H232	0.5968	0.2813	0.5753	0.073*
H233	0.5486	0.2473	0.4674	0.074*
H311	0.2503	0.4394	0.6708	0.092*
H312	0.1343	0.4154	0.6128	0.092*
H511	0.0590	0.5152	0.9434	0.171*	0.50
H512	−0.0290	0.5442	1.0134	0.171*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0390 (2)	0.0677 (2)	0.0570 (2)	−0.0095 (2)	0.0090 (2)	0.0000 (2)
F1	0.0521 (7)	0.1004 (8)	0.0808 (9)	0.0184 (6)	0.0215 (6)	−0.0043 (6)
O1	0.0605 (8)	0.0327 (5)	0.0653 (8)	0.0041 (5)	0.0062 (6)	−0.0089 (5)
O2	0.0586 (8)	0.0417 (6)	0.0636 (8)	−0.0138 (5)	0.0169 (6)	−0.0068 (5)
O3	0.0525 (8)	0.0836 (9)	0.0930 (12)	−0.0131 (7)	0.0221 (7)	−0.0336 (8)
O4	0.1565 (18)	0.1035 (12)	0.0945 (14)	0.0740 (12)	0.0330 (12)	0.0066 (10)
O5	0.128 (3)	0.113 (2)	0.187 (4)	−0.006 (2)	0.069 (3)	−0.063 (2)
N1	0.0302 (6)	0.0348 (6)	0.0338 (7)	0.0007 (5)	0.0072 (5)	0.0018 (5)
N2	0.0520 (9)	0.0364 (7)	0.0569 (9)	−0.0022 (6)	0.0052 (7)	−0.0075 (6)
N3	0.0438 (7)	0.0385 (6)	0.0382 (8)	−0.0016 (5)	0.0120 (6)	−0.0015 (5)
N4	0.0509 (8)	0.0375 (7)	0.0437 (8)	−0.0048 (5)	0.0147 (6)	−0.0015 (5)
C1	0.0379 (8)	0.0349 (7)	0.0430 (9)	−0.0032 (6)	0.0063 (7)	−0.0026 (6)
C2	0.0508 (10)	0.0353 (7)	0.0359 (9)	0.0054 (6)	0.0070 (7)	0.0047 (6)
C3	0.0486 (9)	0.0392 (8)	0.0359 (9)	0.0033 (6)	0.0127 (7)	0.0061 (6)
C4	0.0397 (9)	0.0446 (8)	0.0331 (8)	0.0032 (6)	0.0007 (7)	−0.0001 (6)
C5	0.0429 (9)	0.0435 (8)	0.0322 (8)	0.0040 (6)	0.0036 (7)	−0.0030 (6)
C6	0.0459 (9)	0.0337 (7)	0.0336 (8)	−0.0009 (6)	0.0032 (7)	−0.0028 (6)
C7	0.0471 (9)	0.0340 (7)	0.0330 (8)	0.0032 (6)	0.0054 (7)	−0.0039 (6)
C8	0.0485 (10)	0.0388 (8)	0.0474 (10)	0.0002 (7)	0.0092 (8)	−0.0021 (7)
C9	0.0487 (10)	0.0534 (9)	0.0528 (11)	−0.0045 (8)	0.0107 (8)	−0.0021 (8)
C10	0.0445 (10)	0.0738 (12)	0.0408 (10)	0.0118 (8)	0.0101 (8)	−0.0024 (8)
C11	0.0598 (11)	0.0483 (9)	0.0423 (10)	0.0171 (8)	0.0067 (8)	−0.0055 (7)
C12	0.0541 (10)	0.0373 (8)	0.0356 (9)	0.0046 (7)	0.0022 (7)	−0.0053 (6)
C13	0.0394 (9)	0.0422 (8)	0.0428 (9)	0.0098 (6)	0.0083 (7)	−0.0013 (7)
C14	0.0506 (10)	0.0410 (8)	0.0405 (9)	0.0066 (7)	0.0061 (7)	−0.0013 (7)
C15	0.0462 (9)	0.0379 (7)	0.0311 (8)	0.0011 (6)	0.0065 (7)	−0.0014 (6)
C16	0.0490 (9)	0.0365 (8)	0.0342 (8)	−0.0018 (7)	0.0087 (7)	−0.0019 (6)
C17	0.0447 (10)	0.0587 (10)	0.0533 (11)	0.0006 (8)	0.0135 (8)	−0.0022 (8)
C18	0.0671 (14)	0.0723 (13)	0.0891 (18)	0.0069 (10)	0.0363 (13)	−0.0094 (11)
C19	0.0787 (15)	0.0589 (11)	0.0861 (17)	0.0198 (10)	0.0278 (13)	−0.0052 (10)
C20	0.0775 (14)	0.0393 (9)	0.0673 (13)	0.0023 (8)	0.0296 (11)	−0.0053 (8)
C21	0.0550 (10)	0.0370 (8)	0.0341 (9)	−0.0028 (7)	0.0132 (7)	−0.0013 (6)
C22	0.0461 (9)	0.0450 (8)	0.0325 (8)	−0.0004 (7)	0.0086 (7)	0.0003 (6)
C23	0.0516 (11)	0.0590 (10)	0.0700 (14)	−0.0015 (8)	0.0183 (10)	0.0037 (9)

Geometric parameters (Å, º) top

F1—C10	1.358 (2)	O3—H311	0.901
O1—N2	1.4275 (19)	O3—H312	0.925
O1—C12	1.355 (2)	O4—H411	0.979
O2—C16	1.2320 (19)	O4—H412	0.959
N1—C3	1.4929 (19)	O5—H511	0.909
N1—C4	1.4948 (19)	O5—H512	0.924
N1—C13	1.5004 (19)	N1—H111	0.862
N2—C6	1.3023 (18)	C1—H1	0.980
N3—C16	1.4079 (19)	C2—H21	0.970
N3—C17	1.483 (2)	C2—H22	0.970
N3—C21	1.363 (2)	C3—H31	0.970
N4—C21	1.297 (2)	C3—H32	0.970
N4—C22	1.3772 (19)	C4—H41	0.970
C1—C2	1.530 (2)	C4—H42	0.970
C1—C5	1.533 (2)	C5—H51	0.970
C1—C6	1.504 (2)	C5—H52	0.970
C2—C3	1.516 (2)	C8—H8	0.930
C4—C5	1.517 (2)	C9—H9	0.930
C6—C7	1.435 (2)	C11—H11	0.930
C7—C8	1.404 (2)	C13—H131	0.970
C7—C12	1.390 (2)	C13—H132	0.970
C8—C9	1.371 (2)	C14—H141	0.970
C9—C10	1.398 (2)	C14—H142	0.970
C10—C11	1.361 (2)	C17—H171	0.970
C11—C12	1.385 (2)	C17—H172	0.970
C13—C14	1.519 (2)	C18—H181	0.970
C14—C15	1.509 (2)	C18—H182	0.970
C15—C16	1.428 (2)	C19—H191	0.970
C15—C22	1.361 (2)	C19—H192	0.970
C17—C18	1.501 (2)	C20—H201	0.970
C18—C19	1.481 (3)	C20—H202	0.970
C19—C20	1.490 (3)	C23—H231	0.960
C20—C21	1.505 (2)	C23—H232	0.960
C22—C23	1.498 (2)	C23—H233	0.960

Cl1···O3	3.1048 (14)	H11···H411ⁱⁱ	3.310
Cl1···N1	3.0351 (12)	H11···H412ⁱⁱ	3.507
F1···O2ⁱ	3.5586 (18)	H11···H171ⁱⁱⁱ	2.869
F1···N3ⁱ	3.3503 (18)	H11···H202ⁱ	3.223
F1···C16ⁱ	3.454 (2)	H11···H311ⁱⁱ	2.817
F1···C17ⁱ	3.392 (2)	H11···H312ⁱⁱ	3.003
F1···C23ⁱⁱ	3.485 (2)	H21···Cl1	3.260
O1···O2ⁱⁱⁱ	3.5778 (18)	H21···Cl1ⁱ	3.546
O1···O3ⁱⁱ	3.4342 (18)	H21···C14ⁱ	3.410
O1···O4ⁱⁱ	3.466 (2)	H21···H31ⁱ	3.188
O1···C13ⁱⁱⁱ	3.2876 (18)	H21···H141ⁱ	3.422
O1···C15ⁱⁱⁱ	3.3720 (19)	H21···H142ⁱ	2.583
O1···C16ⁱⁱⁱ	3.259 (2)	H21···H233ⁱ	3.492
O2···F1ⁱ	3.5586 (18)	H22···Cl1ⁱ	3.142
O2···O1^iv	3.5778 (18)	H22···O2^vi	3.504
O2···O3^v	2.8421 (18)	H22···C17^vi	3.216
O2···C3^vi	3.311 (2)	H22···C23ⁱ	3.407
O3···Cl1	3.1048 (14)	H22···H142ⁱ	3.089
O3···O1^vii	3.4342 (18)	H22···H171^vi	2.992
O3···O2^viii	2.8421 (18)	H22···H172^vi	2.584
O3···O4	2.909 (2)	H22···H232ⁱ	3.098
O3···C8	3.5085 (19)	H22···H233ⁱ	2.829
O3···C9	3.343 (2)	H31···Cl1ⁱ	2.971
O3···C13^viii	3.406 (2)	H31···O2^vi	3.462
O4···O1^vii	3.466 (2)	H31···O3ⁱ	3.181
O4···O3	2.909 (2)	H31···H8ⁱ	3.490
O4···O5	2.775 (4)	H31···H21ⁱ	3.188
O4···O5^ix	2.754 (5)	H31···H311ⁱ	2.758
O4···N4^x	2.997 (2)	H31···H312ⁱ	2.873
O5···O4	2.775 (4)	H32···O2^vi	2.476
O5···O4^ix	2.754 (5)	H32···O3ⁱ	3.524
O5···O5^ix	2.320 (5)	H32···C16^vi	3.592
O5···C4^viii	3.481 (4)	H32···H9^v	3.488
O5···C18ⁱⁱⁱ	3.527 (4)	H32···H172^vi	3.076
O5···C19ⁱⁱⁱ	3.331 (4)	H32···H311ⁱ	3.419
N1···Cl1	3.0351 (12)	H32···H312ⁱ	2.850
N2···C13ⁱⁱⁱ	3.4786 (19)	H41···F1^v	3.432
N2···C15ⁱⁱⁱ	3.397 (2)	H41···O4^v	3.182
N2···C22ⁱⁱⁱ	3.331 (2)	H41···O5^v	2.963
N3···F1ⁱ	3.3503 (18)	H41···H411^v	3.039
N3···C10ⁱ	3.544 (2)	H41···H9^v	2.921
N3···C12^iv	3.571 (2)	H41···H511^v	2.697
N4···O4^xi	2.997 (2)	H41···H512^v	3.274
C3···O2^vi	3.311 (2)	H41···H512^xii	3.315
C4···O5^v	3.481 (4)	H42···O4^v	3.329
C8···O3	3.5085 (19)	H42···O5^v	3.332
C8···C14ⁱ	3.512 (2)	H42···O5^xii	3.052
C9···O3	3.343 (2)	H42···C18^x	3.083
C10···N3ⁱ	3.544 (2)	H42···C19^x	3.120
C10···C16ⁱ	3.375 (2)	H42···H411^v	3.392
C12···N3ⁱⁱⁱ	3.571 (2)	H42···H181^x	2.794
C12···C22ⁱ	3.578 (2)	H42···H182^x	2.887
C13···O1^iv	3.2876 (18)	H42···H192^x	2.386
C13···O3^v	3.406 (2)	H42···H511^v	2.995
C13···N2^iv	3.4786 (19)	H42···H511^xii	3.330
C14···C8ⁱ	3.512 (2)	H42···H512^v	3.251
C15···O1^iv	3.3720 (19)	H42···H512^xii	2.960
C15···N2^iv	3.397 (2)	H51···O4^xii	3.461
C16···F1ⁱ	3.454 (2)	H51···O5^v	3.152
C16···O1^iv	3.259 (2)	H51···N4ⁱⁱⁱ	2.799
C16···C10ⁱ	3.375 (2)	H51···C21ⁱⁱⁱ	3.493
C17···F1ⁱ	3.392 (2)	H51···C22ⁱⁱⁱ	3.509
C18···O5^iv	3.527 (4)	H51···C23ⁱⁱⁱ	3.545
C19···O5^iv	3.331 (4)	H51···H412^xii	2.956
C22···N2^iv	3.331 (2)	H51···H201ⁱⁱⁱ	2.935
C22···C12ⁱ	3.578 (2)	H51···H231ⁱⁱⁱ	2.794
C23···F1^vii	3.485 (2)	H51···H511^v	3.464
Cl1···H8	2.983	H51···H511^xii	3.518
Cl1···H11^vii	3.028	H51···H512^v	2.920
Cl1···H21	3.260	H52···Cl1	3.117
Cl1···H21ⁱ	3.546	H52···C19^x	3.473
Cl1···H22ⁱ	3.142	H52···H192^x	2.618
Cl1···H31ⁱ	2.971	H52···H201ⁱⁱⁱ	2.986
Cl1···H52	3.117	H52···H202^x	3.252
Cl1···H111	2.173	H111···Cl1	2.173
Cl1···H132	3.513	H111···H182^x	3.337
Cl1···H142	3.173	H131···O1^iv	3.058
Cl1···H182^x	3.071	H131···O3^v	2.444
Cl1···H202^x	2.987	H131···O4^v	3.543
Cl1···H232	3.107	H131···H411^v	2.829
Cl1···H311	2.214	H131···H311^v	3.326
Cl1···H312	3.251	H131···H312^v	2.321
F1···H1^viii	2.772	H132···Cl1	3.513
F1···H41^viii	3.432	H132···O1^iv	2.717
F1···H172ⁱ	2.762	H132···N2^iv	2.643
F1···H182ⁱ	3.334	H132···C18^x	3.595
F1···H231ⁱⁱ	2.921	H132···H411^v	3.513
F1···H232ⁱⁱ	3.171	H132···H181^x	3.309
O1···H411ⁱⁱ	3.032	H132···H182^x	2.986
O1···H412ⁱⁱ	3.360	H141···O3ⁱ	3.379
O1···H131ⁱⁱⁱ	3.058	H141···C8ⁱ	2.996
O1···H132ⁱⁱⁱ	2.717	H141···C9ⁱ	3.035
O1···H233ⁱ	3.041	H141···H8ⁱ	3.012
O1···H312ⁱⁱ	3.295	H141···H9ⁱ	3.065
O2···H9ⁱ	3.535	H141···H21ⁱ	3.422
O2···H22^vi	3.504	H141···H311ⁱ	3.311
O2···H31^vi	3.462	H141···H312^v	3.506
O2···H32^vi	2.476	H141···H312ⁱ	3.439
O2···H311^v	3.183	H142···Cl1	3.173
O2···H312^v	1.934	H142···C2ⁱ	3.268
O3···H411	1.947	H142···C7ⁱ	3.533
O3···H412	3.360	H142···C8ⁱ	3.370
O3···H8	2.996	H142···H8ⁱ	3.402
O3···H9	2.646	H142···H21ⁱ	2.583
O3···H11^vii	3.069	H142···H22ⁱ	3.089
O3···H31ⁱ	3.181	H171···C10^iv	3.214
O3···H32ⁱ	3.524	H171···C11^iv	2.847
O3···H131^viii	2.444	H171···C12^iv	3.294
O3···H141ⁱ	3.379	H171···H11^iv	2.869
O4···H9	3.288	H171···H22^vi	2.992
O4···H41^viii	3.182	H171···H233^v	3.559
O4···H42^viii	3.329	H171···H312^v	3.514
O4···H51^xii	3.461	H172···F1ⁱ	2.762
O4···H131^viii	3.543	H172···N2^vi	3.478
O4···H201^x	3.395	H172···C1^vi	3.154
O4···H202^x	3.236	H172···C2^vi	3.166
O4···H231^x	3.471	H172···H1^vi	2.461
O4···H311	3.288	H172···H22^vi	2.584
O4···H511	1.871	H172···H32^vi	3.076
O4···H511^ix	3.381	H181···O5^iv	2.835
O4···H512	3.255	H181···N2^vi	3.210
O4···H512^ix	1.898	H181···H42^xi	2.794
O5···H411	3.426	H181···H132^xi	3.309
O5···H411^ix	3.591	H181···H231^v	3.390
O5···H412	3.432	H181···H233^v	3.022
O5···H412^ix	2.982	H181···H511^iv	3.452
O5···H9	3.598	H181···H512^iv	3.253
O5···H41^viii	2.963	H182···Cl1^xi	3.071
O5···H42^viii	3.332	H182···F1ⁱ	3.334
O5···H42^xii	3.052	H182···N2^vi	3.448
O5···H51^viii	3.152	H182···H42^xi	2.887
O5···H181ⁱⁱⁱ	2.835	H182···H111^xi	3.337
O5···H191ⁱⁱⁱ	3.046	H182···H132^xi	2.986
O5···H192ⁱⁱⁱ	3.013	H191···O5^iv	3.046
O5···H231ⁱⁱ	2.922	H191···C7^iv	3.481
O5···H511^ix	2.050	H191···C8^iv	3.074
O5···H512^ix	1.854	H191···C9^iv	2.963
N2···H132ⁱⁱⁱ	2.643	H191···C10^iv	3.274
N2···H172^vi	3.478	H191···H8^iv	3.399
N2···H181^vi	3.210	H191···H9^iv	3.234
N2···H182^vi	3.448	H191···H201^xiii	3.537
N2···H232ⁱⁱⁱ	3.591	H191···H511^iv	3.076
N2···H233ⁱ	2.961	H192···O5^iv	3.013
N4···H411^xi	3.428	H192···C4^xi	3.085
N4···H412^xi	2.039	H192···C5^xi	3.004
N4···H11ⁱ	3.538	H192···H42^xi	2.386
N4···H51^iv	2.799	H192···H51^xi	2.907
C1···H172^vi	3.154	H192···H52^xi	2.618
C2···H142ⁱ	3.268	H192···H201^xiii	2.877
C2···H172^vi	3.166	H192···H511^iv	3.017
C2···H233ⁱ	3.492	H192···H512^iv	3.586
C3···H311ⁱ	3.485	H192···H512^xiv	3.575
C3···H312ⁱ	3.288	H201···O4^xi	3.395
C4···H192^x	3.085	H201···C5^iv	3.409
C4···H511^v	3.249	H201···C19^xiii	3.407
C4···H512^v	3.552	H201···C20^xiii	3.326
C4···H512^xii	3.564	H201···H412^xi	2.840
C5···H192^x	3.004	H201···H51^iv	2.935
C5···H201ⁱⁱⁱ	3.409	H201···H52^iv	2.986
C5···H231ⁱⁱⁱ	3.565	H201···H191^xiii	3.537
C6···H233ⁱ	3.096	H201···H192^xiii	2.877
C7···H142ⁱ	3.533	H201···H201^xiii	2.733
C7···H191ⁱⁱⁱ	3.481	H201···H202^xiii	3.395
C7···H233ⁱ	3.284	H202···Cl1^xi	2.987
C8···H141ⁱ	2.996	H202···O4^xi	3.236
C8···H142ⁱ	3.370	H202···H411^xi	3.197
C8···H191ⁱⁱⁱ	3.074	H202···H412^xi	2.771
C8···H311	3.231	H202···H8^xi	3.489
C9···H141ⁱ	3.035	H202···H11ⁱ	3.223
C9···H191ⁱⁱⁱ	2.963	H202···H52^xi	3.252
C9···H311	3.429	H202···H201^xiii	3.395
C10···H171ⁱⁱⁱ	3.214	H202···H311^xi	3.247
C10···H191ⁱⁱⁱ	3.274	H231···F1^vii	2.921
C11···H171ⁱⁱⁱ	2.847	H231···O4^xi	3.471
C12···H171ⁱⁱⁱ	3.294	H231···O5^vii	2.922
C12···H233ⁱ	3.229	H231···C5^iv	3.565
C13···H411^v	3.561	H231···H1^iv	3.097
C13···H312^v	3.226	H231···H412^xi	2.845
C14···H21ⁱ	3.410	H231···H51^iv	2.794
C16···H32^vi	3.592	H231···H512^vii	3.024
C16···H312^v	2.889	H232···Cl1	3.107
C17···H1^vi	3.405	H232···F1^vii	3.171
C17···H22^vi	3.216	H232···N2^iv	3.591
C18···H42^xi	3.083	H232···H22ⁱ	3.098
C18···H132^xi	3.595	H233···O1ⁱ	3.041
C19···H42^xi	3.120	H233···N2ⁱ	2.961
C19···H52^xi	3.473	H233···C2ⁱ	3.492
C19···H201^xiii	3.407	H233···C6ⁱ	3.096
C19···H511^iv	3.441	H233···C7ⁱ	3.284
C20···H412^xi	2.985	H233···C12ⁱ	3.229
C20···H201^xiii	3.326	H233···H412^xi	3.134
C21···H412^xi	2.819	H233···H21ⁱ	3.492
C21···H11ⁱ	3.402	H233···H22ⁱ	2.829
C21···H51^iv	3.493	H233···H171^viii	3.559
C22···H412^xi	2.973	H233···H181^viii	3.022
C22···H51^iv	3.509	H311···Cl1	2.214
C23···H412^xi	3.153	H311···O2^viii	3.183
C23···H22ⁱ	3.407	H311···O4	3.288
C23···H51^iv	3.545	H311···C3ⁱ	3.485
H1···F1^v	2.772	H311···C8	3.231
H1···C17^vi	3.405	H311···C9	3.429
H1···H172^vi	2.461	H311···H411	2.403
H1···H231ⁱⁱⁱ	3.097	H311···H412	3.572
H411···O1^vii	3.032	H311···H8	2.533
H411···O3	1.947	H311···H9	2.931
H411···O5	3.426	H311···H11^vii	2.817
H411···O5^ix	3.591	H311···H31ⁱ	2.758
H411···N4^x	3.428	H311···H32ⁱ	3.419
H411···C13^viii	3.561	H311···H131^viii	3.326
H411···H9	2.875	H311···H141ⁱ	3.311
H411···H11^vii	3.310	H311···H202^x	3.247
H411···H41^viii	3.039	H312···Cl1	3.251
H411···H42^viii	3.392	H312···O1^vii	3.295
H411···H131^viii	2.829	H312···O2^viii	1.934
H411···H132^viii	3.513	H312···C3ⁱ	3.288
H411···H202^x	3.197	H312···C13^viii	3.226
H411···H311	2.403	H312···C16^viii	2.889
H411···H312	2.677	H312···H411	2.677
H411···H511	2.554	H312···H9	3.393
H411···H512^ix	2.772	H312···H11^vii	3.003
H412···O1^vii	3.360	H312···H31ⁱ	2.873
H412···O3	3.360	H312···H32ⁱ	2.850
H412···O5	3.432	H312···H131^viii	2.321
H412···O5^ix	2.982	H312···H141^viii	3.506
H412···N4^x	2.039	H312···H141ⁱ	3.439
H412···C20^x	2.985	H312···H171^viii	3.514
H412···C21^x	2.819	H511···O4	1.871
H412···C22^x	2.973	H511···O4^ix	3.381
H412···C23^x	3.153	H511···O5^ix	2.050
H412···H11^vii	3.507	H511···C4^viii	3.249
H412···H51^xii	2.956	H511···C19ⁱⁱⁱ	3.441
H412···H201^x	2.840	H511···H411	2.554
H412···H202^x	2.771	H511···H412	2.566
H412···H231^x	2.845	H511···H9	3.275
H412···H233^x	3.134	H511···H41^viii	2.697
H412···H311	3.572	H511···H42^viii	2.995
H412···H511	2.566	H511···H42^xii	3.330
H412···H512^ix	2.236	H511···H51^viii	3.464
H8···Cl1	2.983	H511···H51^xii	3.518
H8···O3	2.996	H511···H181ⁱⁱⁱ	3.452
H8···H31ⁱ	3.490	H511···H191ⁱⁱⁱ	3.076
H8···H141ⁱ	3.012	H511···H192ⁱⁱⁱ	3.017
H8···H142ⁱ	3.402	H511···H511^ix	2.162
H8···H191ⁱⁱⁱ	3.399	H511···H512^ix	1.300
H8···H202^x	3.489	H512···O4	3.255
H8···H311	2.533	H512···O4^ix	1.898
H9···O2ⁱ	3.535	H512···O5^ix	1.854
H9···O3	2.646	H512···C4^viii	3.552
H9···O4	3.288	H512···C4^xii	3.564
H9···O5	3.598	H512···H411^ix	2.772
H9···H411	2.875	H512···H412^ix	2.236
H9···H32^viii	3.488	H512···H41^viii	3.274
H9···H41^viii	2.921	H512···H41^xii	3.315
H9···H141ⁱ	3.065	H512···H42^viii	3.251
H9···H191ⁱⁱⁱ	3.234	H512···H42^xii	2.960
H9···H311	2.931	H512···H51^viii	2.920
H9···H312	3.393	H512···H181ⁱⁱⁱ	3.253
H9···H511	3.275	H512···H192ⁱⁱⁱ	3.586
H11···Cl1ⁱⁱ	3.028	H512···H192^xv	3.575
H11···O3ⁱⁱ	3.069	H512···H231ⁱⁱ	3.024
H11···N4ⁱ	3.538	H512···H511^ix	1.300
H11···C21ⁱ	3.402	H512···H512^ix	1.789

N2—O1—C12	107.80 (11)	C3—C2—H21	108.6
C3—N1—C4	109.77 (10)	C3—C2—H22	108.6
C3—N1—C13	114.52 (12)	H21—C2—H22	109.5
C4—N1—C13	111.61 (10)	N1—C3—H31	109.5
O1—N2—C6	107.03 (13)	N1—C3—H32	109.4
C16—N3—C17	115.75 (12)	C2—C3—H31	109.5
C16—N3—C21	120.66 (14)	C2—C3—H32	109.4
C17—N3—C21	123.58 (13)	H31—C3—H32	109.5
C21—N4—C22	119.30 (13)	N1—C4—H41	109.2
C2—C1—C5	110.14 (12)	N1—C4—H42	109.2
C2—C1—C6	109.25 (12)	C5—C4—H41	109.2
C5—C1—C6	112.58 (14)	C5—C4—H42	109.2
C1—C2—C3	112.90 (12)	H41—C4—H42	109.5
N1—C3—C2	109.53 (13)	C1—C5—H51	108.9
N1—C4—C5	110.54 (11)	C1—C5—H52	109.0
C1—C5—C4	111.58 (14)	C4—C5—H51	108.9
N2—C6—C1	118.89 (15)	C4—C5—H52	108.9
N2—C6—C7	111.51 (14)	H51—C5—H52	109.5
C1—C6—C7	129.48 (12)	C7—C8—H8	120.9
C6—C7—C8	137.02 (14)	C9—C8—H8	120.9
C6—C7—C12	103.84 (13)	C8—C9—H9	120.2
C8—C7—C12	119.13 (15)	C10—C9—H9	120.2
C7—C8—C9	118.16 (14)	C10—C11—H11	123.0
C8—C9—C10	119.53 (16)	C12—C11—H11	123.0
F1—C10—C9	116.78 (16)	N1—C13—H131	108.8
F1—C10—C11	118.31 (16)	N1—C13—H132	108.8
C9—C10—C11	124.91 (18)	C14—C13—H131	108.8
C10—C11—C12	114.04 (15)	C14—C13—H132	108.9
O1—C12—C7	109.81 (15)	H131—C13—H132	109.5
O1—C12—C11	125.95 (14)	C13—C14—H141	108.7
C7—C12—C11	124.23 (15)	C13—C14—H142	108.6
N1—C13—C14	112.00 (11)	C15—C14—H141	108.7
C13—C14—C15	112.71 (12)	C15—C14—H142	108.7
C14—C15—C16	116.41 (13)	H141—C14—H142	109.5
C14—C15—C22	124.26 (15)	N3—C17—H171	108.6
C16—C15—C22	119.32 (14)	N3—C17—H172	108.5
O2—C16—N3	118.78 (15)	C18—C17—H171	108.5
O2—C16—C15	125.30 (14)	C18—C17—H172	108.6
N3—C16—C15	115.92 (13)	H171—C17—H172	109.5
N3—C17—C18	113.13 (14)	C17—C18—H181	108.9
C17—C18—C19	111.8 (2)	C17—C18—H182	108.9
C18—C19—C20	110.04 (17)	C19—C18—H181	108.9
C19—C20—C21	114.85 (15)	C19—C18—H182	108.9
N3—C21—N4	122.92 (14)	H181—C18—H182	109.5
N3—C21—C20	119.06 (16)	C18—C19—H191	109.3
N4—C21—C20	118.02 (14)	C18—C19—H192	109.3
N4—C22—C15	121.85 (16)	C20—C19—H191	109.3
N4—C22—C23	113.98 (13)	C20—C19—H192	109.3
C15—C22—C23	124.16 (15)	H191—C19—H192	109.5
H311—O3—H312	95.3	C19—C20—H201	108.1
H411—O4—H412	107.9	C19—C20—H202	108.1
H511—O5—H512	109.7	C21—C20—H201	108.1
C3—N1—H111	112.0	C21—C20—H202	108.1
C4—N1—H111	105.5	H201—C20—H202	109.5
C13—N1—H111	103.0	C22—C23—H231	109.5
C2—C1—H1	108.3	C22—C23—H232	109.5
C5—C1—H1	108.3	C22—C23—H233	109.5
C6—C1—H1	108.3	H231—C23—H232	109.5
C1—C2—H21	108.7	H231—C23—H233	109.5
C1—C2—H22	108.6	H232—C23—H233	109.5

N2—O1—C12—C7	0.07 (13)	N1—C4—C5—C1	−56.97 (16)
N2—O1—C12—C11	−178.81 (16)	N2—C6—C7—C8	178.56 (18)
C12—O1—N2—C6	−0.37 (17)	N2—C6—C7—C12	−0.48 (18)
C3—N1—C4—C5	61.91 (16)	C1—C6—C7—C8	2.6 (3)
C4—N1—C3—C2	−61.05 (15)	C1—C6—C7—C12	−176.46 (15)
C3—N1—C13—C14	−53.41 (16)	C6—C7—C8—C9	−178.39 (18)
C13—N1—C3—C2	172.50 (11)	C6—C7—C12—O1	0.23 (17)
C4—N1—C13—C14	−178.90 (12)	C6—C7—C12—C11	179.13 (16)
C13—N1—C4—C5	−170.00 (12)	C8—C7—C12—O1	−179.02 (14)
O1—N2—C6—C1	176.99 (12)	C8—C7—C12—C11	−0.1 (2)
O1—N2—C6—C7	0.53 (18)	C12—C7—C8—C9	0.5 (2)
C16—N3—C17—C18	−168.04 (15)	C7—C8—C9—C10	−0.7 (2)
C17—N3—C16—O2	−0.9 (2)	C8—C9—C10—F1	179.65 (16)
C17—N3—C16—C15	178.88 (13)	C8—C9—C10—C11	0.5 (2)
C16—N3—C21—N4	1.1 (2)	F1—C10—C11—C12	−179.21 (15)
C16—N3—C21—C20	−178.67 (14)	C9—C10—C11—C12	−0.1 (2)
C21—N3—C16—O2	178.19 (14)	C10—C11—C12—O1	178.61 (16)
C21—N3—C16—C15	−2.1 (2)	C10—C11—C12—C7	−0.1 (2)
C17—N3—C21—N4	−179.92 (14)	N1—C13—C14—C15	−167.07 (13)
C17—N3—C21—C20	0.3 (2)	C13—C14—C15—C16	−77.62 (18)
C21—N3—C17—C18	12.9 (2)	C13—C14—C15—C22	103.24 (18)
C21—N4—C22—C15	−0.09 (18)	C14—C15—C16—O2	2.5 (2)
C21—N4—C22—C23	−178.73 (15)	C14—C15—C16—N3	−177.18 (13)
C22—N4—C21—N3	0.04 (17)	C14—C15—C22—N4	178.13 (14)
C22—N4—C21—C20	179.82 (14)	C14—C15—C22—C23	−3.4 (2)
C2—C1—C5—C4	50.89 (17)	C16—C15—C22—N4	−1.0 (2)
C5—C1—C2—C3	−51.38 (18)	C16—C15—C22—C23	177.51 (15)
C2—C1—C6—N2	−110.61 (16)	C22—C15—C16—O2	−178.28 (15)
C2—C1—C6—C7	65.1 (2)	C22—C15—C16—N3	2.0 (2)
C6—C1—C2—C3	−175.53 (13)	N3—C17—C18—C19	−43.5 (2)
C5—C1—C6—N2	126.70 (15)	C17—C18—C19—C20	60.7 (2)
C5—C1—C6—C7	−57.6 (2)	C18—C19—C20—C21	−47.0 (2)
C6—C1—C5—C4	173.09 (12)	C19—C20—C21—N3	17.1 (2)
C1—C2—C3—N1	56.74 (16)	C19—C20—C21—N4	−162.66 (17)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+3/2, y−1/2, −z+3/2; (v) x+1, y, z; (vi) −x+2, −y+1, −z+1; (vii) −x+1/2, y−1/2, −z+3/2; (viii) x−1, y, z; (ix) −x, −y+1, −z+2; (x) x−1/2, −y+1/2, z+1/2; (xi) x+1/2, −y+1/2, z−1/2; (xii) −x+1, −y+1, −z+2; (xiii) −x+2, −y, −z+1; (xiv) x+3/2, −y+1/2, z−1/2; (xv) x−3/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H111···Cl1	0.86	2.17	3.0351 (12)	179
O3—H311···Cl1	0.90	2.21	3.1047 (14)	170
O3—H312···O2^viii	0.93	1.93	2.8421 (18)	167
O4—H411···O3	0.98	1.95	2.909 (2)	167
O4—H412···N4^x	0.96	2.04	2.997 (2)	178
O5—H511···O4	0.91	1.87	2.775 (4)	173
O5—H512···O4^ix	0.92	1.90	2.754 (5)	153
O5—H512···O5^ix	0.92	1.85	2.320 (5)	109

Symmetry codes: (viii) x−1, y, z; (ix) −x, −y+1, −z+2; (x) x−1/2, −y+1/2, z+1/2.

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