Crystal structures of N-[(4-phenyl­thia­zol-2-yl)carbamo­thio­yl]benzamide and N-{[4-(4-bromo­phen­yl)thia­zol-2-yl]carbamo­thio­yl}benzamide from synchrotron X-ray diffraction

The crystal structures of two new thio­urea derivatives – potential active pharmaceutical ingredients (APIs) – were studied by synchrotron X-ray diffraction.

Key indicators

Structure: I

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.095
• Data-to-parameter ratio = 16.2

Structure: II

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.092
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     --  C1      ..        5.6 s.u.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.193 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         48 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          4 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         65 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.965 Note
PLAT420_ALERT_2_C D-H Without Acceptor       N2     --  H2     ...     Please Check
PLAT431_ALERT_2_C Short Inter HL..A  Contact Br1    ..  S1      ..       3.35 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  BR1     ..       2.97 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           5 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         91 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          8 Note
PLAT976_ALERT_2_C Check Calcd Residual Density  0.99A From      N2      -0.42 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group     C2/c       I2/a Note
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        125 Note
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           2 Units
PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ           4 Units
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           2 Units
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ           4 Units
PLAT984_ALERT_1_G The  H-f'=     0.000 Deviates from the B&C-Value      0.007 Check

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

For both compounds, data collection: Automar (MarXperts, 2015); cell refinement: iMOSFLM (Battye et al., 2011); data reduction: iMOSFLM (Battye et al., 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) N-[(4-Phenylthiazol-2-yl)carbamothioyl]benzamide

Crystal data

C17H13N3OS2	F(000) = 704
Mr = 339.42	Dx = 1.419 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.96990 Å
a = 12.901 (3) Å	Cell parameters from 600 reflections
b = 5.5160 (11) Å	θ = 2.4–34.0°
c = 23.143 (5) Å	µ = 0.81 mm^−1
β = 105.32 (3)°	T = 100 K
V = 1588.4 (6) Å^3	Prism, colourless
Z = 4	0.15 × 0.10 × 0.05 mm

Data collection

MAR CCD diffractometer	2899 reflections with I > 2σ(I)
φ scan	Rint = 0.033
Absorption correction: multi-scan (SCALA; Evans, 2006)	θmax = 38.5°, θmin = 2.2°
Tmin = 0.870, Tmax = 0.950	h = −16→16
26393 measured reflections	k = −6→7
3395 independent reflections	l = −29→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0566P)^2 + 0.566P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3395 reflections	Δρmax = 0.32 e Å^−3
209 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.0035 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
S1	0.41550 (3)	0.80075 (7)	0.45047 (2)	0.03118 (14)
S2	0.25885 (3)	1.09330 (7)	0.35070 (2)	0.02857 (14)
O1	0.47826 (9)	0.3167 (2)	0.30362 (5)	0.0333 (3)
N1	0.36884 (10)	0.6692 (2)	0.33491 (6)	0.0279 (3)
H1	0.3853	0.5686	0.3068	0.033*
N2	0.49953 (10)	0.4417 (2)	0.40077 (5)	0.0265 (3)
H2	0.5346	0.4048	0.4403	0.032*
N3	0.22879 (10)	0.8127 (2)	0.25771 (6)	0.0270 (3)
C1	0.42612 (12)	0.6327 (3)	0.39203 (7)	0.0262 (3)
C2	0.28765 (12)	0.8397 (3)	0.31264 (7)	0.0265 (3)
C3	0.15407 (12)	0.9994 (3)	0.24243 (7)	0.0266 (3)
C4	0.16011 (13)	1.1685 (3)	0.28659 (7)	0.0291 (3)
H4	0.1159	1.3086	0.2826	0.035*
C5	0.07557 (12)	0.9915 (3)	0.18273 (7)	0.0263 (3)
C6	0.07731 (13)	0.7958 (3)	0.14375 (7)	0.0292 (3)
H6	0.1300	0.6722	0.1555	0.035*
C7	0.00219 (13)	0.7826 (3)	0.08808 (8)	0.0342 (4)
H7	0.0038	0.6496	0.0623	0.041*
C8	−0.07530 (13)	0.9630 (3)	0.06996 (8)	0.0356 (4)
H8	−0.1264	0.9529	0.0320	0.043*
C9	−0.07725 (14)	1.1582 (3)	0.10782 (8)	0.0343 (4)
H9	−0.1298	1.2817	0.0956	0.041*
C10	−0.00247 (13)	1.1736 (3)	0.16369 (7)	0.0303 (4)
H10	−0.0043	1.3080	0.1891	0.036*
C11	0.52613 (12)	0.3002 (3)	0.35705 (7)	0.0268 (3)
C12	0.61647 (12)	0.1241 (3)	0.37854 (6)	0.0259 (3)
C13	0.62162 (12)	−0.0727 (3)	0.34049 (7)	0.0280 (3)
H13	0.5687	−0.0900	0.3034	0.034*
C14	0.70420 (13)	−0.2414 (3)	0.35736 (7)	0.0298 (3)
H14	0.7074	−0.3746	0.3319	0.036*
C15	0.78246 (13)	−0.2151 (3)	0.41177 (7)	0.0318 (4)
H15	0.8389	−0.3304	0.4232	0.038*
C16	0.77780 (13)	−0.0197 (3)	0.44932 (7)	0.0316 (4)
H16	0.8308	−0.0031	0.4864	0.038*
C17	0.69563 (12)	0.1514 (3)	0.43264 (7)	0.0282 (3)
H17	0.6934	0.2859	0.4579	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0401 (2)	0.0298 (2)	0.0231 (2)	0.00420 (17)	0.00737 (16)	−0.00296 (15)
S2	0.0325 (2)	0.0253 (2)	0.0282 (2)	0.00129 (15)	0.00863 (15)	−0.00300 (15)
O1	0.0376 (6)	0.0382 (7)	0.0228 (6)	0.0089 (5)	0.0059 (5)	−0.0010 (5)
N1	0.0319 (7)	0.0282 (7)	0.0236 (6)	0.0033 (6)	0.0075 (5)	−0.0021 (5)
N2	0.0288 (6)	0.0286 (7)	0.0214 (6)	0.0022 (5)	0.0056 (5)	0.0004 (5)
N3	0.0287 (6)	0.0259 (7)	0.0270 (7)	0.0016 (5)	0.0086 (5)	0.0007 (5)
C1	0.0271 (7)	0.0260 (8)	0.0264 (7)	−0.0013 (6)	0.0087 (6)	0.0004 (6)
C2	0.0300 (8)	0.0232 (8)	0.0282 (8)	0.0003 (6)	0.0110 (6)	0.0005 (6)
C3	0.0276 (7)	0.0231 (8)	0.0314 (8)	0.0003 (6)	0.0120 (6)	0.0024 (6)
C4	0.0301 (8)	0.0259 (8)	0.0318 (8)	0.0019 (6)	0.0089 (6)	0.0003 (6)
C5	0.0265 (7)	0.0239 (8)	0.0300 (8)	−0.0012 (6)	0.0103 (6)	0.0026 (6)
C6	0.0272 (7)	0.0254 (8)	0.0342 (8)	0.0016 (6)	0.0066 (6)	−0.0001 (6)
C7	0.0342 (9)	0.0286 (9)	0.0375 (9)	0.0005 (7)	0.0058 (7)	−0.0038 (7)
C8	0.0300 (8)	0.0388 (10)	0.0340 (8)	0.0002 (7)	0.0017 (7)	0.0012 (7)
C9	0.0330 (8)	0.0323 (9)	0.0377 (9)	0.0087 (7)	0.0098 (7)	0.0063 (7)
C10	0.0336 (8)	0.0270 (8)	0.0328 (8)	0.0053 (7)	0.0131 (7)	0.0019 (6)
C11	0.0282 (8)	0.0290 (8)	0.0234 (7)	−0.0012 (6)	0.0074 (6)	0.0001 (6)
C12	0.0274 (7)	0.0271 (8)	0.0243 (7)	−0.0009 (6)	0.0091 (6)	0.0011 (6)
C13	0.0291 (8)	0.0306 (8)	0.0252 (7)	−0.0022 (6)	0.0085 (6)	−0.0013 (6)
C14	0.0336 (8)	0.0287 (8)	0.0301 (8)	0.0000 (7)	0.0135 (6)	−0.0015 (6)
C15	0.0320 (8)	0.0309 (9)	0.0343 (9)	0.0065 (7)	0.0120 (7)	0.0050 (7)
C16	0.0290 (8)	0.0387 (10)	0.0259 (8)	0.0022 (7)	0.0053 (6)	0.0020 (7)
C17	0.0317 (8)	0.0287 (8)	0.0250 (8)	−0.0014 (7)	0.0089 (6)	−0.0011 (6)

Geometric parameters (Å, º)

S1—C1	1.6747 (16)	C7—C8	1.394 (2)
S2—C4	1.7313 (17)	C7—H7	0.9500
S2—C2	1.7447 (16)	C8—C9	1.393 (3)
O1—C11	1.2308 (19)	C8—H8	0.9500
N1—C1	1.348 (2)	C9—C10	1.397 (2)
N1—C2	1.401 (2)	C9—H9	0.9500
N1—H1	0.9210	C10—H10	0.9500
N2—C11	1.3909 (19)	C11—C12	1.498 (2)
N2—C1	1.395 (2)	C12—C17	1.399 (2)
N2—H2	0.9300	C12—C13	1.410 (2)
N3—C2	1.306 (2)	C13—C14	1.391 (2)
N3—C3	1.391 (2)	C13—H13	0.9500
C3—C4	1.371 (2)	C14—C15	1.398 (2)
C3—C5	1.482 (2)	C14—H14	0.9500
C4—H4	0.9500	C15—C16	1.396 (2)
C5—C10	1.408 (2)	C15—H15	0.9500
C5—C6	1.411 (2)	C16—C17	1.395 (2)
C6—C7	1.395 (2)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C4—S2—C2	88.06 (8)	C9—C8—H8	120.2
C1—N1—C2	128.58 (13)	C7—C8—H8	120.2
C1—N1—H1	115.7	C8—C9—C10	120.43 (15)
C2—N1—H1	115.7	C8—C9—H9	119.8
C11—N2—C1	127.36 (13)	C10—C9—H9	119.8
C11—N2—H2	116.3	C9—C10—C5	120.55 (15)
C1—N2—H2	116.3	C9—C10—H10	119.7
C2—N3—C3	110.42 (13)	C5—C10—H10	119.7
N1—C1—N2	115.46 (13)	O1—C11—N2	122.31 (14)
N1—C1—S1	124.67 (12)	O1—C11—C12	121.44 (14)
N2—C1—S1	119.87 (11)	N2—C11—C12	116.25 (13)
N3—C2—N1	117.88 (14)	C17—C12—C13	119.85 (14)
N3—C2—S2	115.87 (12)	C17—C12—C11	123.20 (14)
N1—C2—S2	126.22 (12)	C13—C12—C11	116.92 (13)
C4—C3—N3	114.53 (14)	C14—C13—C12	119.92 (14)
C4—C3—C5	127.25 (14)	C14—C13—H13	120.0
N3—C3—C5	118.17 (14)	C12—C13—H13	120.0
C3—C4—S2	111.10 (12)	C13—C14—C15	120.06 (15)
C3—C4—H4	124.5	C13—C14—H14	120.0
S2—C4—H4	124.5	C15—C14—H14	120.0
C10—C5—C6	118.47 (15)	C16—C15—C14	120.09 (15)
C10—C5—C3	121.79 (14)	C16—C15—H15	120.0
C6—C5—C3	119.73 (14)	C14—C15—H15	120.0
C7—C6—C5	120.38 (15)	C15—C16—C17	120.29 (15)
C7—C6—H6	119.8	C15—C16—H16	119.9
C5—C6—H6	119.8	C17—C16—H16	119.9
C8—C7—C6	120.58 (16)	C16—C17—C12	119.77 (15)
C8—C7—H7	119.7	C16—C17—H17	120.1
C6—C7—H7	119.7	C12—C17—H17	120.1
C9—C8—C7	119.56 (16)
C2—N1—C1—N2	177.74 (14)	C5—C6—C7—C8	0.3 (3)
C2—N1—C1—S1	−3.2 (2)	C6—C7—C8—C9	0.2 (3)
C11—N2—C1—N1	5.9 (2)	C7—C8—C9—C10	−0.2 (3)
C11—N2—C1—S1	−173.23 (12)	C8—C9—C10—C5	−0.4 (2)
C3—N3—C2—N1	−178.70 (13)	C6—C5—C10—C9	0.9 (2)
C3—N3—C2—S2	−0.34 (17)	C3—C5—C10—C9	−178.30 (14)
C1—N1—C2—N3	−166.94 (15)	C1—N2—C11—O1	−6.7 (2)
C1—N1—C2—S2	14.9 (2)	C1—N2—C11—C12	173.58 (14)
C4—S2—C2—N3	−0.53 (12)	O1—C11—C12—C17	157.43 (15)
C4—S2—C2—N1	177.67 (14)	N2—C11—C12—C17	−22.9 (2)
C2—N3—C3—C4	1.36 (19)	O1—C11—C12—C13	−20.5 (2)
C2—N3—C3—C5	−176.47 (13)	N2—C11—C12—C13	159.15 (13)
N3—C3—C4—S2	−1.76 (17)	C17—C12—C13—C14	1.2 (2)
C5—C3—C4—S2	175.84 (12)	C11—C12—C13—C14	179.22 (13)
C2—S2—C4—C3	1.25 (12)	C12—C13—C14—C15	−0.5 (2)
C4—C3—C5—C10	2.7 (2)	C13—C14—C15—C16	0.1 (2)
N3—C3—C5—C10	−179.82 (13)	C14—C15—C16—C17	−0.5 (2)
C4—C3—C5—C6	−176.52 (15)	C15—C16—C17—C12	1.2 (2)
N3—C3—C5—C6	1.0 (2)	C13—C12—C17—C16	−1.6 (2)
C10—C5—C6—C7	−0.9 (2)	C11—C12—C17—C16	−179.47 (14)
C3—C5—C6—C7	178.33 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.92	1.85	2.6145 (18)	139
N2—H2···S1^i	0.93	2.69	3.5845 (15)	162
C13—H13···O1^ii	0.95	2.44	3.299 (2)	150

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

(II) N-{[4-(4-Bromophenyl)thiazol-2-yl]carbamothioyl}benzamide

Crystal data

C17H12BrN3OS2	F(000) = 1680
Mr = 418.33	Dx = 1.681 Mg m^−3
Monoclinic, C2/c	Synchrotron radiation, λ = 0.96990 Å
a = 37.210 (7) Å	Cell parameters from 500 reflections
b = 4.0000 (8) Å	θ = 4.0–33.0°
c = 28.450 (6) Å	µ = 1.56 mm^−1
β = 128.69 (3)°	T = 100 K
V = 3305.2 (18) Å^3	Prism, colourless
Z = 8	0.07 × 0.05 × 0.03 mm

Data collection

MAR CCD diffractometer	2523 reflections with I > 2σ(I)
φ scan	Rint = 0.065
Absorption correction: multi-scan (SCALA; Evans, 2006)	θmax = 38.4°, θmin = 4.0°
Tmin = 0.880, Tmax = 0.930	h = −44→44
13698 measured reflections	k = −4→4
3267 independent reflections	l = −32→32

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.02P)^2] where P = (Fo^2 + 2Fc^2)/3
3267 reflections	(Δ/σ)max = 0.002
217 parameters	Δρmax = 0.62 e Å^−3
0 restraints	Δρmin = −0.78 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	0.66455 (2)	0.24056 (7)	0.96731 (2)	0.02282 (14)
S1	0.67189 (2)	0.95707 (16)	0.58750 (3)	0.02136 (19)
S2	0.70200 (2)	0.97423 (15)	0.71326 (3)	0.01827 (18)
O1	0.55011 (6)	0.3045 (5)	0.53088 (9)	0.0239 (5)
N1	0.62216 (7)	0.6652 (5)	0.61537 (10)	0.0176 (5)
H1	0.5969	0.5551	0.6017	0.021*
N2	0.59498 (7)	0.6073 (5)	0.51692 (9)	0.0194 (5)
H2	0.5969	0.6736	0.4890	0.023*
N3	0.64079 (7)	0.6390 (5)	0.71031 (9)	0.0178 (5)
C1	0.62849 (9)	0.7359 (6)	0.57480 (13)	0.0183 (7)
C2	0.65111 (9)	0.7460 (6)	0.67684 (13)	0.0173 (6)
C3	0.67476 (9)	0.7355 (6)	0.76996 (13)	0.0167 (6)
C4	0.70985 (8)	0.9180 (6)	0.77919 (12)	0.0197 (6)
H4	0.7353	1.0029	0.8172	0.024*
C5	0.67149 (8)	0.6265 (6)	0.81672 (11)	0.0175 (6)
C6	0.71033 (9)	0.6346 (7)	0.87798 (12)	0.0213 (6)
H6	0.7387	0.7176	0.8894	0.026*
C7	0.70779 (8)	0.5233 (6)	0.92191 (12)	0.0219 (7)
H7	0.7343	0.5286	0.9631	0.026*
C8	0.66619 (8)	0.4035 (6)	0.90546 (12)	0.0193 (6)
C9	0.62698 (9)	0.3949 (7)	0.84512 (12)	0.0223 (6)
H9	0.5986	0.3141	0.8340	0.027*
C10	0.63006 (9)	0.5062 (6)	0.80154 (12)	0.0216 (6)
H10	0.6034	0.5006	0.7604	0.026*
C11	0.55924 (8)	0.3889 (6)	0.49790 (12)	0.0187 (6)
C12	0.53267 (9)	0.2627 (6)	0.43455 (13)	0.0184 (7)
C13	0.48960 (8)	0.1152 (7)	0.40853 (12)	0.0216 (6)
H13	0.4785	0.1002	0.4308	0.026*
C14	0.46331 (9)	−0.0089 (6)	0.34991 (12)	0.0239 (7)
H14	0.4341	−0.1062	0.3321	0.029*
C15	0.47950 (9)	0.0089 (6)	0.31750 (13)	0.0253 (7)
H15	0.4613	−0.0754	0.2775	0.030*
C16	0.52255 (9)	0.1505 (7)	0.34332 (13)	0.0262 (7)
H16	0.5337	0.1612	0.3210	0.031*
C17	0.54912 (9)	0.2757 (6)	0.40176 (13)	0.0225 (7)
H17	0.5785	0.3702	0.4194	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0213 (2)	0.0297 (2)	0.0189 (2)	0.00396 (11)	0.01329 (17)	0.00383 (11)
S1	0.0214 (3)	0.0250 (3)	0.0184 (4)	−0.0048 (3)	0.0128 (3)	−0.0023 (3)
S2	0.0148 (3)	0.0215 (3)	0.0161 (4)	−0.0005 (2)	0.0085 (3)	−0.0005 (2)
O1	0.0196 (10)	0.0343 (11)	0.0182 (11)	−0.0039 (8)	0.0119 (9)	0.0011 (8)
N1	0.0130 (10)	0.0241 (11)	0.0136 (12)	−0.0010 (8)	0.0073 (10)	0.0011 (9)
N2	0.0181 (10)	0.0249 (12)	0.0119 (11)	−0.0010 (9)	0.0078 (9)	0.0018 (9)
N3	0.0145 (10)	0.0206 (11)	0.0136 (11)	0.0014 (9)	0.0066 (9)	0.0006 (9)
C1	0.0154 (13)	0.0199 (13)	0.0149 (15)	0.0050 (9)	0.0072 (12)	0.0032 (9)
C2	0.0154 (13)	0.0217 (14)	0.0132 (14)	0.0026 (9)	0.0082 (12)	0.0013 (9)
C3	0.0144 (13)	0.0169 (13)	0.0156 (15)	0.0024 (9)	0.0079 (12)	−0.0009 (9)
C4	0.0179 (12)	0.0214 (13)	0.0144 (14)	0.0000 (10)	0.0075 (11)	−0.0006 (10)
C5	0.0171 (12)	0.0196 (12)	0.0132 (13)	0.0035 (10)	0.0083 (11)	0.0004 (10)
C6	0.0141 (12)	0.0292 (14)	0.0185 (15)	0.0000 (11)	0.0091 (12)	0.0000 (11)
C7	0.0141 (12)	0.0308 (15)	0.0129 (14)	0.0024 (10)	0.0046 (11)	−0.0020 (10)
C8	0.0187 (12)	0.0231 (13)	0.0160 (14)	0.0038 (10)	0.0108 (11)	0.0004 (10)
C9	0.0186 (13)	0.0268 (14)	0.0211 (15)	−0.0028 (11)	0.0122 (12)	−0.0021 (11)
C10	0.0169 (12)	0.0291 (14)	0.0146 (14)	0.0000 (10)	0.0078 (11)	−0.0017 (10)
C11	0.0131 (12)	0.0221 (13)	0.0142 (14)	0.0019 (10)	0.0054 (11)	0.0031 (10)
C12	0.0135 (13)	0.0212 (14)	0.0144 (15)	0.0023 (9)	0.0057 (12)	0.0015 (9)
C13	0.0174 (13)	0.0244 (14)	0.0193 (15)	0.0022 (11)	0.0097 (12)	0.0018 (11)
C14	0.0148 (13)	0.0256 (14)	0.0218 (15)	−0.0017 (10)	0.0068 (12)	−0.0014 (11)
C15	0.0212 (13)	0.0269 (15)	0.0161 (14)	0.0000 (10)	0.0059 (12)	−0.0025 (11)
C16	0.0268 (15)	0.0312 (15)	0.0199 (15)	−0.0015 (12)	0.0142 (13)	−0.0025 (12)
C17	0.0153 (13)	0.0269 (15)	0.0186 (16)	−0.0029 (10)	0.0073 (13)	−0.0004 (10)

Geometric parameters (Å, º)

Br1—C8	1.913 (3)	C6—H6	0.9500
S1—C1	1.670 (3)	C7—C8	1.393 (4)
S2—C4	1.723 (3)	C7—H7	0.9500
S2—C2	1.743 (3)	C8—C9	1.395 (4)
O1—C11	1.228 (4)	C9—C10	1.388 (4)
N1—C1	1.345 (4)	C9—H9	0.9500
N1—C2	1.403 (4)	C10—H10	0.9500
N1—H1	0.8800	C11—C12	1.501 (4)
N2—C11	1.387 (3)	C12—C17	1.401 (5)
N2—C1	1.401 (3)	C12—C13	1.408 (4)
N2—H2	0.8800	C13—C14	1.394 (4)
N3—C2	1.302 (4)	C13—H13	0.9500
N3—C3	1.394 (3)	C14—C15	1.383 (4)
C3—C4	1.370 (4)	C14—H14	0.9500
C3—C5	1.476 (4)	C15—C16	1.398 (4)
C4—H4	0.9500	C15—H15	0.9500
C5—C10	1.401 (4)	C16—C17	1.392 (4)
C5—C6	1.407 (3)	C16—H16	0.9500
C6—C7	1.385 (4)	C17—H17	0.9500
C4—S2—C2	87.75 (14)	C7—C8—Br1	118.4 (2)
C1—N1—C2	127.7 (2)	C9—C8—Br1	120.9 (2)
C1—N1—H1	116.1	C10—C9—C8	119.0 (3)
C2—N1—H1	116.1	C10—C9—H9	120.5
C11—N2—C1	128.4 (3)	C8—C9—H9	120.5
C11—N2—H2	115.8	C9—C10—C5	121.6 (2)
C1—N2—H2	115.8	C9—C10—H10	119.2
C2—N3—C3	110.0 (2)	C5—C10—H10	119.2
N1—C1—N2	115.3 (2)	O1—C11—N2	122.0 (3)
N1—C1—S1	126.2 (2)	O1—C11—C12	122.4 (2)
N2—C1—S1	118.6 (2)	N2—C11—C12	115.6 (3)
N3—C2—N1	119.2 (2)	C17—C12—C13	119.6 (3)
N3—C2—S2	116.4 (2)	C17—C12—C11	123.6 (2)
N1—C2—S2	124.3 (2)	C13—C12—C11	116.8 (3)
C4—C3—N3	114.3 (3)	C14—C13—C12	119.7 (3)
C4—C3—C5	126.2 (2)	C14—C13—H13	120.2
N3—C3—C5	119.5 (2)	C12—C13—H13	120.2
C3—C4—S2	111.6 (2)	C15—C14—C13	120.4 (3)
C3—C4—H4	124.2	C15—C14—H14	119.8
S2—C4—H4	124.2	C13—C14—H14	119.8
C10—C5—C6	118.1 (3)	C14—C15—C16	120.3 (3)
C10—C5—C3	121.2 (2)	C14—C15—H15	119.9
C6—C5—C3	120.7 (2)	C16—C15—H15	119.9
C7—C6—C5	120.9 (3)	C17—C16—C15	119.9 (3)
C7—C6—H6	119.5	C17—C16—H16	120.1
C5—C6—H6	119.5	C15—C16—H16	120.1
C6—C7—C8	119.7 (2)	C16—C17—C12	120.2 (3)
C6—C7—H7	120.1	C16—C17—H17	119.9
C8—C7—H7	120.1	C12—C17—H17	119.9
C7—C8—C9	120.7 (3)
C2—N1—C1—N2	176.6 (2)	C6—C7—C8—C9	−0.1 (4)
C2—N1—C1—S1	−3.2 (4)	C6—C7—C8—Br1	178.3 (2)
C11—N2—C1—N1	−7.5 (4)	C7—C8—C9—C10	0.3 (4)
C11—N2—C1—S1	172.2 (2)	Br1—C8—C9—C10	−178.0 (2)
C3—N3—C2—N1	177.7 (2)	C8—C9—C10—C5	0.0 (4)
C3—N3—C2—S2	−0.5 (3)	C6—C5—C10—C9	−0.5 (4)
C1—N1—C2—N3	−175.8 (2)	C3—C5—C10—C9	178.3 (2)
C1—N1—C2—S2	2.2 (4)	C1—N2—C11—O1	7.4 (4)
C4—S2—C2—N3	0.2 (2)	C1—N2—C11—C12	−172.4 (2)
C4—S2—C2—N1	−177.9 (2)	O1—C11—C12—C17	−161.6 (2)
C2—N3—C3—C4	0.6 (3)	N2—C11—C12—C17	18.2 (3)
C2—N3—C3—C5	−176.9 (2)	O1—C11—C12—C13	16.4 (4)
N3—C3—C4—S2	−0.5 (3)	N2—C11—C12—C13	−163.8 (2)
C5—C3—C4—S2	176.8 (2)	C17—C12—C13—C14	−1.6 (4)
C2—S2—C4—C3	0.17 (19)	C11—C12—C13—C14	−179.6 (2)
C4—C3—C5—C10	165.8 (2)	C12—C13—C14—C15	0.7 (4)
N3—C3—C5—C10	−17.0 (4)	C13—C14—C15—C16	0.3 (4)
C4—C3—C5—C6	−15.5 (4)	C14—C15—C16—C17	−0.4 (4)
N3—C3—C5—C6	161.7 (2)	C15—C16—C17—C12	−0.5 (4)
C10—C5—C6—C7	0.7 (4)	C13—C12—C17—C16	1.5 (4)
C3—C5—C6—C7	−178.1 (2)	C11—C12—C17—C16	179.4 (2)
C5—C6—C7—C8	−0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.93	2.644 (3)	138
N2—H2···Br1^i	0.88	2.97	3.692 (3)	141
C13—H13···O1^ii	0.95	2.53	3.340 (4)	144

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