N-[4-(2-Oxo-2H-chromen-3-yl)-3-phenyl-3H-thia­zol-2-yl­idene]anilinium bromide methanol solvate

In the title structure, C₂₄H₁₇N₂O₂S⁺·Br⁻·CH₃OH, the cations, anions and solvent mol­ecules form centrosymmetric clusters via a combination of inter­molecular N—H...O, O—H...Br and C—H...Br inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.092
• Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1    ..  S1      ..       3.20 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

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

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

N-[4-(2-Oxo-2H-chromen-3-yl)-3-phenyl-3H-thiazol-2-ylidene]anilinium bromide methanol solvate

Crystal data

C24H17N2O2S^+·Br^−·CH4O	Z = 2
Mr = 509.41	F(000) = 520
Triclinic, P1	Dx = 1.515 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5909 (1) Å	Cell parameters from 37016 reflections
b = 10.9374 (1) Å	θ = 2.0–30.0°
c = 11.0418 (2) Å	µ = 1.96 mm^−1
α = 82.2188 (8)°	T = 160 K
β = 62.9030 (6)°	Prism, colourless
γ = 79.2876 (8)°	0.28 × 0.25 × 0.20 mm
V = 1116.93 (2) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	6538 independent reflections
Radiation source: Nonius FR590 sealed tube generator	5532 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.057
Detector resolution: 10 pixels mm^-1	θmax = 30.0°, θmin = 2.1°
φ and ω scans with κ offsets	h = −14→14
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −15→15
Tmin = 0.565, Tmax = 0.678	l = −15→15
31111 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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.3319P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
6538 reflections	Δρmax = 0.56 e Å^−3
299 parameters	Δρmin = −0.57 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.089 (3)

Special details

Experimental. Solvent used: MeOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.447 (1) Frames collected: 753 Seconds exposure per frame: 10 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 30.0

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
S1	0.34396 (4)	0.45180 (4)	0.47933 (4)	0.01926 (10)
O41	0.42036 (14)	−0.09078 (11)	0.71941 (14)	0.0255 (3)
O42	0.30681 (15)	0.00728 (13)	0.60161 (16)	0.0319 (3)
N3	0.22315 (14)	0.31129 (13)	0.69259 (14)	0.0176 (3)
N21	0.07269 (15)	0.49531 (13)	0.67969 (15)	0.0189 (3)
H21	0.000 (3)	0.471 (2)	0.744 (2)	0.027 (6)*
C2	0.19820 (17)	0.42168 (15)	0.63120 (16)	0.0179 (3)
C4	0.36273 (17)	0.24953 (15)	0.62103 (17)	0.0187 (3)
C5	0.43885 (18)	0.31166 (16)	0.50450 (17)	0.0206 (3)
H5	0.5343	0.2822	0.4425	0.025*
C21	0.04956 (18)	0.61375 (15)	0.61460 (16)	0.0185 (3)
C22	0.14511 (19)	0.69909 (16)	0.57640 (19)	0.0238 (3)
H22	0.2270	0.6796	0.5934	0.029*
C23	0.1197 (2)	0.81339 (17)	0.5130 (2)	0.0285 (4)
H23	0.1854	0.8717	0.4848	0.034*
C24	−0.0017 (2)	0.84229 (17)	0.4907 (2)	0.0298 (4)
H24	−0.0174	0.9193	0.4449	0.036*
C25	−0.0999 (2)	0.75899 (17)	0.5352 (2)	0.0281 (4)
H25	−0.1850	0.7807	0.5236	0.034*
C26	−0.07430 (19)	0.64388 (17)	0.59674 (18)	0.0231 (3)
H26	−0.1410	0.5863	0.6263	0.028*
C31	0.11776 (17)	0.26791 (15)	0.82335 (17)	0.0183 (3)
C32	0.0930 (2)	0.32448 (17)	0.93871 (18)	0.0248 (4)
H32	0.1472	0.3872	0.9325	0.030*
C33	−0.0128 (2)	0.28755 (19)	1.06330 (19)	0.0307 (4)
H33	−0.0316	0.3256	1.1433	0.037*
C34	−0.0909 (2)	0.19586 (18)	1.0721 (2)	0.0302 (4)
H34	−0.1631	0.1711	1.1579	0.036*
C35	−0.0638 (2)	0.14027 (18)	0.9559 (2)	0.0305 (4)
H35	−0.1173	0.0769	0.9623	0.037*
C36	0.0410 (2)	0.17621 (17)	0.82970 (19)	0.0253 (4)
H36	0.0593	0.1385	0.7496	0.030*
C42	0.37537 (19)	0.01636 (16)	0.66146 (18)	0.0233 (3)
C43	0.41513 (18)	0.13224 (15)	0.67738 (17)	0.0197 (3)
C44	0.50542 (19)	0.13010 (16)	0.73350 (18)	0.0226 (3)
H44	0.5332	0.2058	0.7399	0.027*
C45	0.6552 (2)	0.00577 (18)	0.8413 (2)	0.0320 (4)
H45	0.6909	0.0780	0.8449	0.038*
C46	0.6972 (2)	−0.1083 (2)	0.8930 (2)	0.0371 (5)
H46	0.7626	−0.1144	0.9313	0.045*
C47	0.6441 (2)	−0.21433 (19)	0.8892 (2)	0.0361 (5)
H47	0.6721	−0.2919	0.9267	0.043*
C48	0.5510 (2)	−0.20840 (18)	0.8315 (2)	0.0318 (4)
H48	0.5152	−0.2808	0.8284	0.038*
C49	0.51150 (19)	−0.09351 (16)	0.77837 (19)	0.0240 (3)
C50	0.55996 (19)	0.01471 (16)	0.78368 (19)	0.0236 (3)
O52	0.19235 (14)	0.55060 (14)	0.12625 (15)	0.0303 (3)
H52	0.222 (3)	0.539 (3)	0.047 (3)	0.043 (7)*
C51	0.2752 (3)	0.6140 (2)	0.1611 (3)	0.0445 (5)
H511	0.2949	0.6915	0.1040	0.067*
H512	0.3658	0.5610	0.1462	0.067*
H513	0.2222	0.6335	0.2572	0.067*
Br1	0.624322 (18)	0.480547 (18)	0.198808 (18)	0.02805 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01656 (18)	0.0218 (2)	0.01647 (18)	−0.00477 (15)	−0.00482 (15)	0.00206 (15)
O41	0.0259 (6)	0.0193 (6)	0.0321 (7)	−0.0045 (5)	−0.0131 (6)	−0.0008 (5)
O42	0.0331 (7)	0.0301 (7)	0.0398 (8)	−0.0052 (6)	−0.0209 (7)	−0.0067 (6)
N3	0.0156 (6)	0.0191 (6)	0.0154 (6)	−0.0035 (5)	−0.0049 (5)	0.0015 (5)
N21	0.0146 (6)	0.0198 (7)	0.0184 (7)	−0.0032 (5)	−0.0047 (5)	0.0026 (5)
C2	0.0175 (7)	0.0204 (7)	0.0165 (7)	−0.0056 (6)	−0.0076 (6)	0.0007 (6)
C4	0.0161 (7)	0.0201 (8)	0.0190 (7)	−0.0024 (6)	−0.0068 (6)	−0.0022 (6)
C5	0.0173 (7)	0.0214 (8)	0.0202 (8)	−0.0021 (6)	−0.0058 (6)	−0.0019 (6)
C21	0.0196 (7)	0.0183 (7)	0.0160 (7)	−0.0012 (6)	−0.0067 (6)	−0.0015 (6)
C22	0.0215 (8)	0.0233 (8)	0.0255 (8)	−0.0043 (7)	−0.0091 (7)	−0.0011 (7)
C23	0.0315 (10)	0.0203 (8)	0.0304 (10)	−0.0067 (7)	−0.0099 (8)	−0.0008 (7)
C24	0.0449 (11)	0.0184 (8)	0.0290 (9)	−0.0014 (8)	−0.0204 (9)	0.0001 (7)
C25	0.0325 (10)	0.0248 (9)	0.0313 (10)	0.0023 (7)	−0.0192 (8)	−0.0046 (7)
C26	0.0240 (8)	0.0239 (8)	0.0243 (8)	−0.0029 (7)	−0.0131 (7)	−0.0018 (7)
C31	0.0152 (7)	0.0188 (7)	0.0173 (7)	−0.0025 (6)	−0.0052 (6)	0.0028 (6)
C32	0.0249 (8)	0.0293 (9)	0.0200 (8)	−0.0100 (7)	−0.0082 (7)	0.0006 (7)
C33	0.0323 (10)	0.0369 (10)	0.0186 (8)	−0.0087 (8)	−0.0062 (8)	−0.0010 (7)
C34	0.0240 (9)	0.0318 (10)	0.0235 (9)	−0.0067 (7)	−0.0021 (7)	0.0068 (7)
C35	0.0280 (9)	0.0268 (9)	0.0322 (10)	−0.0124 (7)	−0.0081 (8)	0.0049 (8)
C36	0.0271 (9)	0.0235 (8)	0.0248 (9)	−0.0078 (7)	−0.0098 (7)	0.0001 (7)
C42	0.0205 (8)	0.0210 (8)	0.0243 (8)	−0.0020 (6)	−0.0060 (7)	−0.0044 (7)
C43	0.0172 (7)	0.0180 (7)	0.0200 (8)	−0.0026 (6)	−0.0048 (6)	−0.0014 (6)
C44	0.0224 (8)	0.0192 (8)	0.0240 (8)	−0.0031 (6)	−0.0083 (7)	−0.0014 (6)
C45	0.0341 (10)	0.0274 (9)	0.0402 (11)	−0.0028 (8)	−0.0225 (9)	0.0006 (8)
C46	0.0385 (11)	0.0375 (11)	0.0413 (12)	0.0019 (9)	−0.0257 (10)	−0.0010 (9)
C47	0.0401 (11)	0.0273 (10)	0.0365 (11)	0.0047 (8)	−0.0180 (9)	0.0026 (8)
C48	0.0338 (10)	0.0215 (9)	0.0350 (11)	−0.0021 (8)	−0.0121 (9)	0.0008 (8)
C49	0.0214 (8)	0.0222 (8)	0.0241 (8)	−0.0005 (6)	−0.0072 (7)	−0.0022 (7)
C50	0.0226 (8)	0.0214 (8)	0.0252 (8)	−0.0009 (6)	−0.0101 (7)	−0.0010 (7)
O52	0.0220 (6)	0.0402 (8)	0.0224 (7)	−0.0081 (6)	−0.0038 (5)	0.0009 (6)
C51	0.0403 (12)	0.0597 (15)	0.0418 (13)	−0.0175 (11)	−0.0240 (11)	0.0066 (11)
Br1	0.02183 (11)	0.03659 (13)	0.02210 (11)	−0.01148 (7)	−0.00354 (7)	−0.00292 (7)

Geometric parameters (Å, º)

S1—C2	1.7276 (17)	C32—H32	0.9500
S1—C5	1.7329 (17)	C33—C34	1.382 (3)
O41—C42	1.370 (2)	C33—H33	0.9500
O41—C49	1.383 (2)	C34—C35	1.382 (3)
O42—C42	1.206 (2)	C34—H34	0.9500
N3—C2	1.345 (2)	C35—C36	1.391 (3)
N3—C4	1.405 (2)	C35—H35	0.9500
N3—C31	1.449 (2)	C36—H36	0.9500
N21—C2	1.331 (2)	C42—C43	1.463 (2)
N21—C21	1.430 (2)	C43—C44	1.352 (2)
N21—H21	0.84 (2)	C44—C50	1.437 (2)
C4—C5	1.338 (2)	C44—H44	0.9500
C4—C43	1.475 (2)	C45—C46	1.383 (3)
C5—H5	0.9500	C45—C50	1.401 (3)
C21—C26	1.388 (2)	C45—H45	0.9500
C21—C22	1.389 (2)	C46—C47	1.393 (3)
C22—C23	1.391 (3)	C46—H46	0.9500
C22—H22	0.9500	C47—C48	1.385 (3)
C23—C24	1.388 (3)	C47—H47	0.9500
C23—H23	0.9500	C48—C49	1.388 (3)
C24—C25	1.385 (3)	C48—H48	0.9500
C24—H24	0.9500	C49—C50	1.393 (3)
C25—C26	1.389 (3)	O52—C51	1.416 (3)
C25—H25	0.9500	O52—H52	0.80 (3)
C26—H26	0.9500	C51—H511	0.9800
C31—C36	1.380 (2)	C51—H512	0.9800
C31—C32	1.386 (2)	C51—H513	0.9800
C32—C33	1.387 (3)
C2—S1—C5	89.81 (8)	C35—C34—C33	119.84 (18)
C42—O41—C49	122.40 (14)	C35—C34—H34	120.1
C2—N3—C4	112.85 (13)	C33—C34—H34	120.1
C2—N3—C31	122.02 (13)	C34—C35—C36	120.63 (18)
C4—N3—C31	125.00 (13)	C34—C35—H35	119.7
C2—N21—C21	122.33 (15)	C36—C35—H35	119.7
C2—N21—H21	121.6 (15)	C31—C36—C35	118.52 (17)
C21—N21—H21	115.7 (15)	C31—C36—H36	120.7
N21—C2—N3	123.26 (15)	C35—C36—H36	120.7
N21—C2—S1	124.48 (13)	O42—C42—O41	117.45 (16)
N3—C2—S1	112.18 (12)	O42—C42—C43	125.59 (17)
C5—C4—N3	112.63 (14)	O41—C42—C43	116.96 (15)
C5—C4—C43	126.14 (15)	C44—C43—C42	120.60 (16)
N3—C4—C43	121.17 (14)	C44—C43—C4	121.25 (15)
C4—C5—S1	112.48 (13)	C42—C43—C4	117.99 (15)
C4—C5—H5	123.8	C43—C44—C50	120.82 (16)
S1—C5—H5	123.8	C43—C44—H44	119.6
C26—C21—C22	120.74 (16)	C50—C44—H44	119.6
C26—C21—N21	118.40 (15)	C46—C45—C50	119.98 (19)
C22—C21—N21	120.79 (15)	C46—C45—H45	120.0
C21—C22—C23	119.34 (17)	C50—C45—H45	120.0
C21—C22—H22	120.3	C45—C46—C47	120.19 (19)
C23—C22—H22	120.3	C45—C46—H46	119.9
C24—C23—C22	120.07 (18)	C47—C46—H46	119.9
C24—C23—H23	120.0	C48—C47—C46	121.03 (19)
C22—C23—H23	120.0	C48—C47—H47	119.5
C25—C24—C23	120.11 (17)	C46—C47—H47	119.5
C25—C24—H24	119.9	C47—C48—C49	118.03 (19)
C23—C24—H24	119.9	C47—C48—H48	121.0
C24—C25—C26	120.20 (17)	C49—C48—H48	121.0
C24—C25—H25	119.9	O41—C49—C48	116.76 (17)
C26—C25—H25	119.9	O41—C49—C50	120.92 (16)
C21—C26—C25	119.43 (17)	C48—C49—C50	122.33 (18)
C21—C26—H26	120.3	C49—C50—C45	118.41 (16)
C25—C26—H26	120.3	C49—C50—C44	117.84 (16)
C36—C31—C32	121.85 (16)	C45—C50—C44	123.71 (17)
C36—C31—N3	119.79 (15)	C51—O52—H52	116 (2)
C32—C31—N3	118.30 (15)	O52—C51—H511	109.5
C31—C32—C33	118.54 (17)	O52—C51—H512	109.5
C31—C32—H32	120.7	H511—C51—H512	109.5
C33—C32—H32	120.7	O52—C51—H513	109.5
C34—C33—C32	120.62 (18)	H511—C51—H513	109.5
C34—C33—H33	119.7	H512—C51—H513	109.5
C32—C33—H33	119.7
C21—N21—C2—N3	178.40 (15)	C32—C33—C34—C35	0.0 (3)
C21—N21—C2—S1	−5.1 (2)	C33—C34—C35—C36	−0.4 (3)
C4—N3—C2—N21	178.93 (15)	C32—C31—C36—C35	−0.1 (3)
C31—N3—C2—N21	−5.0 (2)	N3—C31—C36—C35	−177.24 (16)
C4—N3—C2—S1	2.07 (17)	C34—C35—C36—C31	0.4 (3)
C31—N3—C2—S1	178.11 (12)	C49—O41—C42—O42	173.31 (16)
C5—S1—C2—N21	−177.74 (15)	C49—O41—C42—C43	−6.6 (2)
C5—S1—C2—N3	−0.94 (13)	O42—C42—C43—C44	−172.69 (18)
C2—N3—C4—C5	−2.5 (2)	O41—C42—C43—C44	7.2 (2)
C31—N3—C4—C5	−178.36 (15)	O42—C42—C43—C4	2.7 (3)
C2—N3—C4—C43	174.76 (15)	O41—C42—C43—C4	−177.42 (14)
C31—N3—C4—C43	−1.1 (2)	C5—C4—C43—C44	73.4 (2)
N3—C4—C5—S1	1.72 (19)	N3—C4—C43—C44	−103.4 (2)
C43—C4—C5—S1	−175.34 (13)	C5—C4—C43—C42	−102.0 (2)
C2—S1—C5—C4	−0.48 (14)	N3—C4—C43—C42	81.2 (2)
C2—N21—C21—C26	134.22 (17)	C42—C43—C44—C50	−2.5 (3)
C2—N21—C21—C22	−49.0 (2)	C4—C43—C44—C50	−177.73 (16)
C26—C21—C22—C23	−3.4 (3)	C50—C45—C46—C47	−0.6 (3)
N21—C21—C22—C23	179.84 (16)	C45—C46—C47—C48	1.3 (3)
C21—C22—C23—C24	1.2 (3)	C46—C47—C48—C49	−0.4 (3)
C22—C23—C24—C25	1.9 (3)	C42—O41—C49—C48	−178.94 (17)
C23—C24—C25—C26	−2.9 (3)	C42—O41—C49—C50	1.2 (3)
C22—C21—C26—C25	2.4 (3)	C47—C48—C49—O41	178.95 (18)
N21—C21—C26—C25	179.25 (16)	C47—C48—C49—C50	−1.2 (3)
C24—C25—C26—C21	0.7 (3)	O41—C49—C50—C45	−178.31 (17)
C2—N3—C31—C36	104.48 (19)	C48—C49—C50—C45	1.9 (3)
C4—N3—C31—C36	−80.0 (2)	O41—C49—C50—C44	3.7 (3)
C2—N3—C31—C32	−72.8 (2)	C48—C49—C50—C44	−176.11 (18)
C4—N3—C31—C32	102.75 (19)	C46—C45—C50—C49	−0.9 (3)
C36—C31—C32—C33	−0.3 (3)	C46—C45—C50—C44	176.95 (19)
N3—C31—C32—C33	176.88 (16)	C43—C44—C50—C49	−3.0 (3)
C31—C32—C33—C34	0.4 (3)	C43—C44—C50—C45	179.16 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O52^i	0.84 (2)	1.92 (2)	2.734 (2)	165 (2)
O52—H52···Br1^ii	0.80 (3)	2.46 (3)	3.2412 (15)	164 (3)
C32—H32···Br1^iii	0.95	2.75	3.6296 (18)	153

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