Crystal structures of vortioxetine and its methanol monosolvate

Vortioxetine, a new drug used to treat patients with major depressive disorder, has been crystallized as the free base and its methanol monosolvate. In both structures, the vortioxetine mol­ecules have similar conformations.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.185
• Data-to-parameter ratio = 19.5

Structure: 2

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.156
• Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     --  C9      ..        7.0 su
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0049 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor        N2     -   H2A    ..     Please Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.815 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...          5 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         25 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     --  C5      ..        5.3 su
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....         S1 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....         C4 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     14.313 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.433 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...          6 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

Computing details

For both compounds, data collection: PROCESS-AUTO (Rigaku, 2007); cell refinement: PROCESS-AUTO (Rigaku, 2007); data reduction: CrystalStructure (Rigaku, 2007); 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); software used to prepare material for publication: WinGX (Farrugia, 2012).

(1) 1-{2-[(2,4-Dimethylphenyl)sulfanyl]phenyl}piperazine

Crystal data

C18H22N2S	Z = 2
Mr = 298.44	F(000) = 320
Triclinic, P1	Dx = 1.196 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6160 (4) Å	Cell parameters from 5189 reflections
b = 8.3267 (5) Å	θ = 3.0–27.4°
c = 13.9011 (7) Å	µ = 0.19 mm^−1
α = 84.999 (2)°	T = 296 K
β = 77.631 (1)°	Chunk, colorless
γ = 74.347 (2)°	0.48 × 0.38 × 0.16 mm
V = 828.75 (8) Å^3

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer	3756 independent reflections
Radiation source: rotating anode	2072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR: Higashi, 1995)	k = −10→10
Tmin = 0.904, Tmax = 0.970	l = −18→17
8178 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.185	w = 1/[σ^2(Fo^2) + (0.0622P)^2 + 0.7569P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3756 reflections	Δρmax = 0.40 e Å^−3
193 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.072 (7)

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.

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.

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

	x	y	z	Uiso*/Ueq
C1	0.6391 (4)	0.3576 (4)	0.1355 (2)	0.0428 (7)
C2	0.6226 (5)	0.1944 (5)	0.1467 (3)	0.0549 (8)
H2	0.5698	0.1559	0.2079	0.066*
C3	0.6828 (5)	0.0891 (5)	0.0688 (3)	0.0641 (10)
H3	0.6711	−0.0198	0.0781	0.077*
C4	0.7608 (5)	0.1436 (5)	−0.0235 (3)	0.0575 (9)
C5	0.7753 (4)	0.3054 (5)	−0.0349 (2)	0.0520 (8)
H5	0.8265	0.3428	−0.0969	0.062*
C6	0.7165 (4)	0.4163 (4)	0.0425 (2)	0.0446 (7)
C7	0.8231 (6)	0.0284 (6)	−0.1104 (3)	0.0894 (14)
H7A	0.8791	0.0843	−0.1673	0.134*
H7B	0.7174	−0.0007	−0.1241	0.134*
H7C	0.9121	−0.0710	−0.0948	0.134*
C8	0.7350 (5)	0.5916 (4)	0.0254 (3)	0.0573 (9)
H8A	0.8268	0.6061	0.0592	0.086*
H8B	0.6175	0.6680	0.0498	0.086*
H8C	0.7727	0.6130	−0.0440	0.086*
C9	0.7492 (4)	0.5017 (4)	0.2771 (2)	0.0429 (7)
C10	0.9282 (4)	0.4087 (4)	0.2382 (2)	0.0478 (8)
H10	0.9473	0.3388	0.1862	0.057*
C11	1.0770 (4)	0.4193 (4)	0.2761 (2)	0.0526 (8)
H11	1.1958	0.3563	0.2496	0.063*
C12	1.0515 (4)	0.5228 (5)	0.3533 (2)	0.0568 (9)
H12	1.1525	0.5293	0.3789	0.068*
C13	0.8738 (4)	0.6169 (4)	0.3921 (2)	0.0523 (8)
H13	0.8565	0.6869	0.4438	0.063*
C14	0.7213 (4)	0.6081 (4)	0.3550 (2)	0.0420 (7)
C15	0.4781 (5)	0.8573 (4)	0.3382 (2)	0.0542 (8)
H15A	0.5081	0.8376	0.2681	0.065*
H15B	0.5450	0.9350	0.3504	0.065*
C16	0.2704 (5)	0.9311 (5)	0.3705 (3)	0.0643 (10)
H16A	0.2338	1.0370	0.3356	0.077*
H16B	0.2040	0.8566	0.3535	0.077*
C17	0.2816 (5)	0.8026 (5)	0.5307 (2)	0.0561 (9)
H17A	0.2164	0.7227	0.5196	0.067*
H17B	0.2516	0.8238	0.6006	0.067*
C18	0.4901 (4)	0.7287 (4)	0.4994 (2)	0.0485 (8)
H18A	0.5568	0.8049	0.5140	0.058*
H18B	0.5278	0.6242	0.5354	0.058*
N1	0.5348 (3)	0.7000 (3)	0.39293 (16)	0.0425 (6)
N2	0.2190 (4)	0.9568 (4)	0.4764 (2)	0.0692 (9)
H2A	0.1597	1.0506	0.5030	0.083*
S1	0.54672 (10)	0.48897 (12)	0.23790 (6)	0.0524 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0376 (15)	0.0479 (18)	0.0434 (15)	−0.0111 (13)	−0.0076 (12)	−0.0052 (13)
C2	0.0553 (19)	0.057 (2)	0.0552 (19)	−0.0189 (16)	−0.0121 (16)	−0.0012 (16)
C3	0.069 (2)	0.048 (2)	0.079 (3)	−0.0141 (17)	−0.022 (2)	−0.0033 (18)
C4	0.0539 (19)	0.058 (2)	0.061 (2)	−0.0015 (16)	−0.0194 (17)	−0.0219 (17)
C5	0.0440 (17)	0.067 (2)	0.0425 (16)	−0.0091 (15)	−0.0087 (14)	−0.0079 (15)
C6	0.0372 (15)	0.0502 (19)	0.0458 (16)	−0.0103 (13)	−0.0077 (13)	−0.0024 (13)
C7	0.088 (3)	0.095 (3)	0.086 (3)	−0.005 (3)	−0.023 (2)	−0.048 (3)
C8	0.055 (2)	0.055 (2)	0.064 (2)	−0.0212 (16)	−0.0089 (16)	0.0014 (17)
C9	0.0402 (15)	0.0448 (18)	0.0375 (14)	−0.0075 (13)	0.0005 (12)	0.0006 (12)
C10	0.0390 (15)	0.056 (2)	0.0437 (16)	−0.0090 (14)	0.0006 (13)	−0.0094 (14)
C11	0.0346 (15)	0.066 (2)	0.0540 (18)	−0.0071 (14)	−0.0076 (14)	−0.0083 (16)
C12	0.0426 (17)	0.074 (3)	0.058 (2)	−0.0168 (16)	−0.0161 (15)	−0.0066 (17)
C13	0.0475 (18)	0.065 (2)	0.0488 (17)	−0.0172 (15)	−0.0110 (15)	−0.0141 (15)
C14	0.0410 (15)	0.0452 (18)	0.0378 (14)	−0.0113 (13)	−0.0035 (12)	−0.0012 (12)
C15	0.059 (2)	0.048 (2)	0.0475 (17)	−0.0077 (15)	−0.0032 (15)	0.0013 (14)
C16	0.064 (2)	0.051 (2)	0.065 (2)	0.0022 (17)	−0.0102 (18)	0.0045 (17)
C17	0.0546 (19)	0.061 (2)	0.0459 (17)	−0.0119 (16)	0.0054 (15)	−0.0107 (15)
C18	0.0516 (18)	0.057 (2)	0.0376 (15)	−0.0142 (15)	−0.0066 (13)	−0.0097 (14)
N1	0.0423 (13)	0.0423 (15)	0.0367 (12)	−0.0054 (11)	−0.0013 (10)	−0.0033 (10)
N2	0.071 (2)	0.0517 (19)	0.0656 (18)	0.0063 (15)	0.0048 (16)	−0.0124 (15)
S1	0.0349 (4)	0.0732 (6)	0.0475 (5)	−0.0108 (4)	−0.0023 (3)	−0.0186 (4)

Geometric parameters (Å, º)

C1—C2	1.391 (5)	C11—C12	1.384 (5)
C1—C6	1.406 (4)	C11—H11	0.9300
C1—S1	1.773 (3)	C12—C13	1.388 (4)
C2—C3	1.373 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.389 (4)
C3—C4	1.386 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—N1	1.430 (4)
C4—C5	1.374 (5)	C15—N1	1.464 (4)
C4—C7	1.522 (5)	C15—C16	1.517 (5)
C5—C6	1.398 (4)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C6—C8	1.497 (5)	C16—N2	1.459 (4)
C7—H7A	0.9600	C16—H16A	0.9700
C7—H7B	0.9600	C16—H16B	0.9700
C7—H7C	0.9600	C17—N2	1.449 (4)
C8—H8A	0.9600	C17—C18	1.521 (4)
C8—H8B	0.9600	C17—H17A	0.9700
C8—H8C	0.9600	C17—H17B	0.9700
C9—C10	1.392 (4)	C18—N1	1.472 (4)
C9—C14	1.403 (4)	C18—H18A	0.9700
C9—S1	1.773 (3)	C18—H18B	0.9700
C10—C11	1.373 (4)	N2—H2A	0.8600
C10—H10	0.9300
C2—C1—C6	119.3 (3)	C11—C12—H12	120.3
C2—C1—S1	118.4 (2)	C13—C12—H12	120.3
C6—C1—S1	122.2 (2)	C14—C13—C12	121.1 (3)
C3—C2—C1	121.2 (3)	C14—C13—H13	119.5
C3—C2—H2	119.4	C12—C13—H13	119.5
C1—C2—H2	119.4	C13—C14—C9	118.9 (3)
C2—C3—C4	120.6 (4)	C13—C14—N1	123.5 (3)
C2—C3—H3	119.7	C9—C14—N1	117.5 (3)
C4—C3—H3	119.7	N1—C15—C16	109.5 (3)
C5—C4—C3	118.3 (3)	N1—C15—H15A	109.8
C5—C4—C7	121.0 (4)	C16—C15—H15A	109.8
C3—C4—C7	120.7 (4)	N1—C15—H15B	109.8
C4—C5—C6	122.9 (3)	C16—C15—H15B	109.8
C4—C5—H5	118.6	H15A—C15—H15B	108.2
C6—C5—H5	118.6	N2—C16—C15	111.3 (3)
C5—C6—C1	117.7 (3)	N2—C16—H16A	109.4
C5—C6—C8	120.4 (3)	C15—C16—H16A	109.4
C1—C6—C8	121.9 (3)	N2—C16—H16B	109.4
C4—C7—H7A	109.5	C15—C16—H16B	109.4
C4—C7—H7B	109.5	H16A—C16—H16B	108.0
H7A—C7—H7B	109.5	N2—C17—C18	111.5 (3)
C4—C7—H7C	109.5	N2—C17—H17A	109.3
H7A—C7—H7C	109.5	C18—C17—H17A	109.3
H7B—C7—H7C	109.5	N2—C17—H17B	109.3
C6—C8—H8A	109.5	C18—C17—H17B	109.3
C6—C8—H8B	109.5	H17A—C17—H17B	108.0
H8A—C8—H8B	109.5	N1—C18—C17	108.9 (3)
C6—C8—H8C	109.5	N1—C18—H18A	109.9
H8A—C8—H8C	109.5	C17—C18—H18A	109.9
H8B—C8—H8C	109.5	N1—C18—H18B	109.9
C10—C9—C14	119.6 (3)	C17—C18—H18B	109.9
C10—C9—S1	124.1 (2)	H18A—C18—H18B	108.3
C14—C9—S1	116.3 (2)	C14—N1—C15	112.9 (2)
C11—C10—C9	120.5 (3)	C14—N1—C18	115.5 (2)
C11—C10—H10	119.7	C15—N1—C18	110.2 (2)
C9—C10—H10	119.7	C17—N2—C16	110.8 (3)
C10—C11—C12	120.6 (3)	C17—N2—H2A	124.6
C10—C11—H11	119.7	C16—N2—H2A	124.6
C12—C11—H11	119.7	C9—S1—C1	102.76 (14)
C11—C12—C13	119.3 (3)
C6—C1—C2—C3	0.9 (5)	C10—C9—C14—C13	−0.6 (4)
S1—C1—C2—C3	176.7 (3)	S1—C9—C14—C13	176.8 (2)
C1—C2—C3—C4	−0.4 (5)	C10—C9—C14—N1	−179.5 (3)
C2—C3—C4—C5	−0.3 (5)	S1—C9—C14—N1	−2.1 (3)
C2—C3—C4—C7	−178.4 (3)	N1—C15—C16—N2	57.3 (4)
C3—C4—C5—C6	0.6 (5)	N2—C17—C18—N1	−57.9 (4)
C7—C4—C5—C6	178.7 (3)	C13—C14—N1—C15	95.2 (4)
C4—C5—C6—C1	−0.1 (5)	C9—C14—N1—C15	−85.9 (3)
C4—C5—C6—C8	−179.7 (3)	C13—C14—N1—C18	−32.8 (4)
C2—C1—C6—C5	−0.6 (4)	C9—C14—N1—C18	146.1 (3)
S1—C1—C6—C5	−176.2 (2)	C16—C15—N1—C14	169.7 (3)
C2—C1—C6—C8	178.9 (3)	C16—C15—N1—C18	−59.5 (4)
S1—C1—C6—C8	3.3 (4)	C17—C18—N1—C14	−171.1 (3)
C14—C9—C10—C11	0.6 (5)	C17—C18—N1—C15	59.5 (3)
S1—C9—C10—C11	−176.6 (2)	C18—C17—N2—C16	56.1 (4)
C9—C10—C11—C12	−0.1 (5)	C15—C16—N2—C17	−55.7 (4)
C10—C11—C12—C13	−0.3 (5)	C10—C9—S1—C1	−6.7 (3)
C11—C12—C13—C14	0.3 (5)	C14—C9—S1—C1	176.0 (2)
C12—C13—C14—C9	0.1 (5)	C2—C1—S1—C9	106.2 (3)
C12—C13—C14—N1	179.0 (3)	C6—C1—S1—C9	−78.2 (3)

(2) 1-{2-[(2,4-Dimethylphenyl)sulfanyl]phenyl}piperazine methanol monosolvate

Crystal data

C18H22N2S·CH4O	F(000) = 712
Mr = 330.48	Dx = 1.156 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10380 reflections
a = 13.2100 (7) Å	θ = 3.2–27.4°
b = 18.1500 (9) Å	µ = 0.18 mm^−1
c = 8.1746 (4) Å	T = 296 K
β = 104.378 (2)°	Chunk, colorless
V = 1898.57 (17) Å^3	0.38 × 0.33 × 0.28 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer	4331 independent reflections
Radiation source: rotating anode	2468 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 10.00 pixels mm^-1	θmax = 27.4°, θmin = 3.2°
ω scans	h = −16→17
Absorption correction: multi-scan (ABSCOR: Higashi, 1995)	k = −23→23
Tmin = 0.928, Tmax = 0.952	l = −10→10
18365 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.156	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 0.7465P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.001
4331 reflections	Δρmax = 0.25 e Å^−3
213 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (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.

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.

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

	x	y	z	Uiso*/Ueq
C16	0.7959 (2)	0.35981 (14)	0.6308 (3)	0.0631 (7)
H16A	0.7446	0.3322	0.6726	0.076*
H16B	0.7810	0.3521	0.5097	0.076*
C15	0.78325 (19)	0.44056 (13)	0.6641 (3)	0.0590 (6)
H15A	0.7148	0.4573	0.6018	0.071*
H15B	0.7892	0.4484	0.7835	0.071*
C18	0.96814 (19)	0.45883 (14)	0.7082 (3)	0.0604 (6)
H18A	0.9744	0.4667	0.8277	0.073*
H18B	1.0219	0.4875	0.6754	0.073*
C17	0.9822 (2)	0.37770 (14)	0.6748 (3)	0.0628 (7)
H17A	0.9841	0.3717	0.5577	0.075*
H17B	1.0490	0.3615	0.7446	0.075*
C14	0.84554 (18)	0.55978 (12)	0.5953 (3)	0.0500 (5)
C13	0.89399 (19)	0.61073 (14)	0.7155 (3)	0.0579 (6)
H13	0.9419	0.5948	0.8126	0.069*
C12	0.8721 (2)	0.68494 (14)	0.6929 (3)	0.0644 (7)
H12	0.9049	0.7186	0.7747	0.077*
C11	0.8017 (2)	0.70901 (14)	0.5493 (3)	0.0645 (7)
H11	0.7865	0.7590	0.5348	0.077*
C10	0.7535 (2)	0.65945 (13)	0.4267 (3)	0.0600 (6)
H10	0.7056	0.6761	0.3302	0.072*
C9	0.77610 (18)	0.58456 (12)	0.4466 (3)	0.0520 (6)
C1	0.6514 (2)	0.56877 (13)	0.1194 (3)	0.0560 (6)
C6	0.5482 (2)	0.58898 (14)	0.1102 (3)	0.0612 (6)
C5	0.4947 (2)	0.62711 (16)	−0.0328 (4)	0.0738 (8)
H5	0.4261	0.6413	−0.0401	0.089*
C4	0.5387 (2)	0.64500 (16)	−0.1649 (3)	0.0723 (8)
C3	0.6398 (2)	0.62274 (17)	−0.1533 (3)	0.0743 (8)
H3	0.6708	0.6328	−0.2413	0.089*
C2	0.6953 (2)	0.58576 (15)	−0.0131 (3)	0.0650 (7)
H2	0.7638	0.5718	−0.0070	0.078*
C8	0.4960 (3)	0.5711 (2)	0.2494 (4)	0.0946 (10)
H8A	0.4280	0.5935	0.2252	0.142*
H8B	0.5376	0.5897	0.3546	0.142*
H8C	0.4890	0.5186	0.2571	0.142*
C7	0.4764 (3)	0.6864 (2)	−0.3175 (5)	0.1267 (15)
H7A	0.5232	0.7121	−0.3704	0.190*
H7B	0.4311	0.7212	−0.2825	0.190*
H7C	0.4351	0.6523	−0.3962	0.190*
C19	0.8246 (3)	0.1517 (2)	0.6374 (5)	0.1043 (11)
H19A	0.8628	0.1474	0.7534	0.156*
H19B	0.8153	0.1036	0.5866	0.156*
H19C	0.7576	0.1734	0.6317	0.156*
N1	0.86499 (14)	0.48236 (10)	0.6108 (2)	0.0520 (5)
N2	0.89994 (17)	0.33031 (11)	0.7085 (2)	0.0601 (5)
H2A	0.9160	0.3296	0.8171	0.090*
O1	0.87917 (19)	0.19532 (11)	0.5525 (2)	0.0848 (6)
H1	0.8925	0.2349	0.6017	0.127*
S1	0.72717 (6)	0.51680 (4)	0.29023 (9)	0.0699 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C16	0.0652 (16)	0.0537 (14)	0.0744 (16)	−0.0033 (12)	0.0246 (13)	0.0061 (12)
C15	0.0560 (15)	0.0559 (15)	0.0708 (15)	0.0007 (11)	0.0263 (12)	0.0091 (12)
C18	0.0550 (15)	0.0564 (15)	0.0679 (15)	0.0030 (12)	0.0117 (12)	0.0056 (12)
C17	0.0605 (15)	0.0587 (16)	0.0700 (15)	0.0089 (12)	0.0179 (12)	0.0051 (12)
C14	0.0514 (13)	0.0455 (13)	0.0583 (13)	0.0004 (10)	0.0232 (10)	0.0031 (10)
C13	0.0568 (15)	0.0582 (15)	0.0588 (14)	−0.0015 (12)	0.0149 (11)	−0.0027 (11)
C12	0.0692 (17)	0.0522 (15)	0.0726 (16)	−0.0061 (13)	0.0193 (13)	−0.0104 (12)
C11	0.0738 (17)	0.0441 (13)	0.0795 (17)	0.0015 (12)	0.0265 (14)	−0.0004 (12)
C10	0.0660 (16)	0.0479 (14)	0.0657 (15)	0.0032 (12)	0.0158 (12)	0.0040 (11)
C9	0.0538 (14)	0.0469 (13)	0.0585 (13)	0.0014 (11)	0.0197 (11)	0.0017 (10)
C1	0.0587 (15)	0.0494 (13)	0.0603 (14)	−0.0020 (11)	0.0154 (11)	−0.0061 (10)
C6	0.0576 (15)	0.0588 (15)	0.0684 (15)	−0.0071 (12)	0.0183 (12)	−0.0078 (12)
C5	0.0520 (15)	0.0746 (19)	0.087 (2)	0.0034 (13)	0.0023 (14)	−0.0083 (15)
C4	0.076 (2)	0.0682 (18)	0.0647 (16)	−0.0061 (15)	0.0024 (14)	0.0004 (13)
C3	0.079 (2)	0.084 (2)	0.0612 (16)	−0.0154 (16)	0.0194 (14)	−0.0003 (14)
C2	0.0552 (15)	0.0723 (18)	0.0686 (16)	−0.0039 (13)	0.0173 (12)	−0.0070 (13)
C8	0.089 (2)	0.106 (3)	0.102 (2)	−0.012 (2)	0.0492 (19)	−0.0035 (19)
C7	0.138 (4)	0.125 (3)	0.094 (3)	0.014 (3)	−0.014 (2)	0.026 (2)
C19	0.111 (3)	0.101 (3)	0.113 (3)	−0.031 (2)	0.049 (2)	−0.009 (2)
N1	0.0503 (11)	0.0459 (11)	0.0609 (11)	0.0022 (9)	0.0158 (9)	0.0081 (8)
N2	0.0708 (14)	0.0516 (12)	0.0599 (12)	0.0050 (10)	0.0201 (10)	0.0058 (9)
O1	0.1255 (18)	0.0678 (13)	0.0686 (12)	−0.0129 (12)	0.0384 (12)	−0.0116 (9)
S1	0.0871 (5)	0.0482 (4)	0.0669 (4)	0.0070 (3)	0.0050 (3)	−0.0044 (3)

Geometric parameters (Å, º)

C16—N2	1.465 (3)	C9—S1	1.776 (2)
C16—C15	1.507 (4)	C1—C2	1.384 (3)
C16—H16A	0.9700	C1—C6	1.395 (4)
C16—H16B	0.9700	C1—S1	1.774 (2)
C15—N1	1.471 (3)	C6—C5	1.391 (4)
C15—H15A	0.9700	C6—C8	1.506 (4)
C15—H15B	0.9700	C5—C4	1.386 (4)
C18—N1	1.461 (3)	C5—H5	0.9300
C18—C17	1.517 (3)	C4—C3	1.376 (4)
C18—H18A	0.9700	C4—C7	1.513 (4)
C18—H18B	0.9700	C3—C2	1.373 (4)
C17—N2	1.464 (3)	C3—H3	0.9300
C17—H17A	0.9700	C2—H2	0.9300
C17—H17B	0.9700	C8—H8A	0.9600
C14—C13	1.385 (3)	C8—H8B	0.9600
C14—C9	1.403 (3)	C8—H8C	0.9600
C14—N1	1.428 (3)	C7—H7A	0.9600
C13—C12	1.380 (3)	C7—H7B	0.9600
C13—H13	0.9300	C7—H7C	0.9600
C12—C11	1.375 (4)	C19—O1	1.370 (4)
C12—H12	0.9300	C19—H19A	0.9600
C11—C10	1.379 (3)	C19—H19B	0.9600
C11—H11	0.9300	C19—H19C	0.9600
C10—C9	1.393 (3)	N2—H2A	0.8598
C10—H10	0.9300	O1—H1	0.8200
N2—C16—C15	114.3 (2)	C2—C1—S1	118.1 (2)
N2—C16—H16A	108.7	C6—C1—S1	122.3 (2)
C15—C16—H16A	108.7	C5—C6—C1	117.5 (2)
N2—C16—H16B	108.7	C5—C6—C8	120.7 (3)
C15—C16—H16B	108.7	C1—C6—C8	121.8 (3)
H16A—C16—H16B	107.6	C4—C5—C6	123.2 (3)
N1—C15—C16	109.0 (2)	C4—C5—H5	118.4
N1—C15—H15A	109.9	C6—C5—H5	118.4
C16—C15—H15A	109.9	C3—C4—C5	117.7 (3)
N1—C15—H15B	109.9	C3—C4—C7	121.5 (3)
C16—C15—H15B	109.9	C5—C4—C7	120.8 (3)
H15A—C15—H15B	108.3	C2—C3—C4	120.6 (3)
N1—C18—C17	109.0 (2)	C2—C3—H3	119.7
N1—C18—H18A	109.9	C4—C3—H3	119.7
C17—C18—H18A	109.9	C3—C2—C1	121.5 (3)
N1—C18—H18B	109.9	C3—C2—H2	119.3
C17—C18—H18B	109.9	C1—C2—H2	119.3
H18A—C18—H18B	108.3	C6—C8—H8A	109.5
N2—C17—C18	114.0 (2)	C6—C8—H8B	109.5
N2—C17—H17A	108.8	H8A—C8—H8B	109.5
C18—C17—H17A	108.8	C6—C8—H8C	109.5
N2—C17—H17B	108.8	H8A—C8—H8C	109.5
C18—C17—H17B	108.8	H8B—C8—H8C	109.5
H17A—C17—H17B	107.7	C4—C7—H7A	109.5
C13—C14—C9	119.2 (2)	C4—C7—H7B	109.5
C13—C14—N1	123.6 (2)	H7A—C7—H7B	109.5
C9—C14—N1	117.2 (2)	C4—C7—H7C	109.5
C12—C13—C14	120.8 (2)	H7A—C7—H7C	109.5
C12—C13—H13	119.6	H7B—C7—H7C	109.5
C14—C13—H13	119.6	O1—C19—H19A	109.5
C11—C12—C13	120.0 (2)	O1—C19—H19B	109.5
C11—C12—H12	120.0	H19A—C19—H19B	109.5
C13—C12—H12	120.0	O1—C19—H19C	109.5
C12—C11—C10	120.4 (2)	H19A—C19—H19C	109.5
C12—C11—H11	119.8	H19B—C19—H19C	109.5
C10—C11—H11	119.8	C14—N1—C18	117.31 (19)
C11—C10—C9	120.3 (2)	C14—N1—C15	113.85 (18)
C11—C10—H10	119.9	C18—N1—C15	109.97 (18)
C9—C10—H10	119.9	C17—N2—C16	111.36 (19)
C10—C9—C14	119.3 (2)	C17—N2—H2A	101.4
C10—C9—S1	124.22 (18)	C16—N2—H2A	114.7
C14—C9—S1	116.39 (17)	C19—O1—H1	109.5
C2—C1—C6	119.5 (2)	C1—S1—C9	103.41 (11)
N2—C16—C15—N1	54.9 (3)	C6—C5—C4—C7	179.9 (3)
N1—C18—C17—N2	−55.2 (3)	C5—C4—C3—C2	−1.6 (4)
C9—C14—C13—C12	2.2 (4)	C7—C4—C3—C2	179.4 (3)
N1—C14—C13—C12	179.8 (2)	C4—C3—C2—C1	0.9 (4)
C14—C13—C12—C11	−0.3 (4)	C6—C1—C2—C3	0.6 (4)
C13—C12—C11—C10	−0.6 (4)	S1—C1—C2—C3	176.9 (2)
C12—C11—C10—C9	−0.4 (4)	C13—C14—N1—C18	−28.7 (3)
C11—C10—C9—C14	2.3 (4)	C9—C14—N1—C18	149.0 (2)
C11—C10—C9—S1	−174.67 (19)	C13—C14—N1—C15	101.7 (3)
C13—C14—C9—C10	−3.1 (3)	C9—C14—N1—C15	−80.6 (3)
N1—C14—C9—C10	179.1 (2)	C17—C18—N1—C14	−166.5 (2)
C13—C14—C9—S1	174.04 (18)	C17—C18—N1—C15	61.3 (3)
N1—C14—C9—S1	−3.7 (3)	C16—C15—N1—C14	164.7 (2)
C2—C1—C6—C5	−1.3 (4)	C16—C15—N1—C18	−61.3 (3)
S1—C1—C6—C5	−177.42 (19)	C18—C17—N2—C16	48.1 (3)
C2—C1—C6—C8	179.2 (3)	C15—C16—N2—C17	−48.2 (3)
S1—C1—C6—C8	3.0 (4)	C2—C1—S1—C9	100.2 (2)
C1—C6—C5—C4	0.6 (4)	C6—C1—S1—C9	−83.6 (2)
C8—C6—C5—C4	−179.9 (3)	C10—C9—S1—C1	1.0 (2)
C6—C5—C4—C3	0.9 (4)	C14—C9—S1—C1	−176.04 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^i	0.86	2.15	2.930 (3)	151
O1—H1···N2	0.82	1.93	2.744 (3)	171

Symmetry code: (i) x, −y+1/2, z+1/2.