N-(2-Bromo­thia­zol-5-ylmethyl)phthalimide

The title compound, C₁₂H₇BrN₂O₂S, is an very important inter­mediate in the synthesis of thia­zole compounds. In the structure of the title compound, the phthalimide ring system and the thiazole ring are both planar, and the dihedral angle is 120°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.022
• wR factor = 0.061
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.58
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O1      ..       3.32 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.580
            Tmax scaled      0.141 Tmin scaled      0.131

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

N-(2-Bromothiazol-5-ylmethyl-phthalimide

Crystal data

C12H7BrN2O2S	Z = 2
Mr = 323.17	F(000) = 320
Triclinic, P1	Dx = 1.839 Mg m^−3
a = 7.3539 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6315 (17) Å	Cell parameters from 5374 reflections
c = 9.794 (2) Å	θ = 3.5–27.6°
α = 108.16 (3)°	µ = 3.69 mm^−1
β = 93.79 (3)°	T = 293 K
γ = 96.41 (3)°	Block, colorless
V = 583.7 (2) Å^3	0.57 × 0.56 × 0.53 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer	2149 independent reflections
Radiation source: rotating anode	2047 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ? ω? scans	θmax = 25.5°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→8
Tmin = 0.227, Tmax = 0.244	k = −10→10
4808 measured reflections	l = −11→11

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.061	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0379P)^2 + 0.2605P] where P = (Fo^2 + 2Fc^2)/3
2149 reflections	(Δ/σ)max = 0.011
163 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.26 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.

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	0.94313 (7)	0.43152 (6)	0.23665 (5)	0.02123 (13)
Br1	1.29782 (3)	0.50119 (3)	0.09808 (2)	0.02712 (10)
O1	0.5523 (2)	−0.13862 (18)	0.14712 (15)	0.0271 (3)
O2	0.7628 (2)	0.33948 (17)	0.51216 (15)	0.0263 (3)
N1	0.6441 (2)	0.1221 (2)	0.30952 (17)	0.0191 (3)
N2	1.0169 (3)	0.2322 (2)	−0.00235 (18)	0.0270 (4)
C1	0.6907 (3)	−0.2443 (2)	0.4113 (2)	0.0227 (4)
H1A	0.6440	−0.3410	0.3374	0.027*
C2	0.7697 (3)	−0.2468 (3)	0.5447 (2)	0.0264 (5)
H2B	0.7763	−0.3472	0.5600	0.032*
C3	0.8378 (3)	−0.1023 (3)	0.6535 (2)	0.0248 (4)
H3A	0.8908	−0.1077	0.7405	0.030*
C4	0.8296 (3)	0.0514 (3)	0.6371 (2)	0.0209 (4)
H4A	0.8745	0.1484	0.7111	0.025*
C5	0.7512 (3)	0.0524 (2)	0.5049 (2)	0.0173 (4)
C6	0.6852 (2)	−0.0923 (2)	0.3944 (2)	0.0175 (4)
C7	0.6168 (3)	−0.0498 (2)	0.2658 (2)	0.0190 (4)
C8	0.7250 (3)	0.1932 (2)	0.4520 (2)	0.0192 (4)
C9	0.6123 (3)	0.2170 (3)	0.2121 (2)	0.0221 (4)
H9A	0.5665	0.3176	0.2642	0.026*
H9B	0.5195	0.1536	0.1336	0.026*
C10	0.7857 (3)	0.2589 (2)	0.1513 (2)	0.0191 (4)
C11	0.8500 (3)	0.1702 (3)	0.0292 (2)	0.0260 (5)
H11A	0.7844	0.0714	−0.0310	0.031*
C12	1.0777 (3)	0.3684 (2)	0.0982 (2)	0.0201 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0210 (3)	0.0191 (2)	0.0214 (2)	0.00034 (19)	0.0021 (2)	0.0043 (2)
Br1	0.02010 (14)	0.03319 (15)	0.03100 (14)	−0.00087 (9)	0.00233 (9)	0.01615 (10)
O1	0.0265 (8)	0.0279 (8)	0.0216 (7)	0.0006 (6)	−0.0039 (6)	0.0029 (6)
O2	0.0314 (8)	0.0170 (7)	0.0275 (7)	−0.0007 (6)	0.0006 (7)	0.0047 (6)
N1	0.0201 (8)	0.0193 (8)	0.0188 (8)	0.0000 (6)	0.0000 (7)	0.0087 (7)
N2	0.0274 (10)	0.0290 (10)	0.0223 (8)	0.0021 (7)	0.0047 (8)	0.0053 (7)
C1	0.0200 (10)	0.0185 (10)	0.0282 (10)	0.0030 (8)	0.0022 (8)	0.0054 (8)
C2	0.0247 (11)	0.0261 (11)	0.0343 (11)	0.0093 (9)	0.0067 (9)	0.0157 (9)
C3	0.0232 (11)	0.0342 (12)	0.0215 (10)	0.0108 (9)	0.0046 (9)	0.0127 (9)
C4	0.0187 (9)	0.0258 (10)	0.0180 (9)	0.0038 (8)	0.0040 (8)	0.0062 (8)
C5	0.0135 (9)	0.0193 (9)	0.0197 (9)	0.0031 (7)	0.0047 (8)	0.0064 (8)
C6	0.0136 (9)	0.0199 (9)	0.0194 (9)	0.0031 (7)	0.0039 (8)	0.0063 (8)
C7	0.0135 (9)	0.0213 (10)	0.0211 (9)	0.0018 (7)	0.0027 (8)	0.0053 (8)
C8	0.0155 (9)	0.0214 (10)	0.0204 (9)	0.0014 (7)	0.0044 (8)	0.0062 (8)
C9	0.0193 (10)	0.0248 (10)	0.0250 (10)	0.0005 (8)	−0.0011 (8)	0.0138 (8)
C10	0.0197 (9)	0.0193 (10)	0.0193 (9)	0.0004 (7)	−0.0027 (8)	0.0093 (8)
C11	0.0277 (11)	0.0236 (10)	0.0228 (10)	−0.0031 (8)	−0.0007 (9)	0.0050 (8)
C12	0.0190 (9)	0.0234 (10)	0.0211 (9)	0.0035 (8)	0.0019 (8)	0.0115 (8)

Geometric parameters (Å, º)

S1—C12	1.718 (2)	C2—H2B	0.9300
S1—C10	1.724 (2)	C3—C4	1.392 (3)
Br1—C12	1.876 (2)	C3—H3A	0.9300
O1—C7	1.206 (2)	C4—C5	1.384 (3)
O2—C8	1.206 (2)	C4—H4A	0.9300
N1—C7	1.397 (3)	C5—C6	1.385 (3)
N1—C8	1.398 (3)	C5—C8	1.488 (3)
N1—C9	1.461 (2)	C6—C7	1.490 (3)
N2—C12	1.286 (3)	C9—C10	1.497 (3)
N2—C11	1.376 (3)	C9—H9A	0.9700
C1—C6	1.377 (3)	C9—H9B	0.9700
C1—C2	1.402 (3)	C10—C11	1.351 (3)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.380 (3)
C12—S1—C10	88.60 (10)	C5—C6—C7	108.53 (16)
C7—N1—C8	112.65 (16)	O1—C7—N1	124.96 (18)
C7—N1—C9	123.66 (16)	O1—C7—C6	129.87 (19)
C8—N1—C9	123.30 (16)	N1—C7—C6	105.16 (16)
C12—N2—C11	108.60 (18)	O2—C8—N1	124.23 (18)
C6—C1—C2	117.04 (19)	O2—C8—C5	130.40 (18)
C6—C1—H1A	121.5	N1—C8—C5	105.37 (16)
C2—C1—H1A	121.5	N1—C9—C10	111.17 (16)
C3—C2—C1	120.86 (19)	N1—C9—H9A	109.4
C3—C2—H2B	119.6	C10—C9—H9A	109.4
C1—C2—H2B	119.6	N1—C9—H9B	109.4
C2—C3—C4	122.02 (18)	C10—C9—H9B	109.4
C2—C3—H3A	119.0	H9A—C9—H9B	108.0
C4—C3—H3A	119.0	C11—C10—C9	127.84 (19)
C5—C4—C3	116.62 (19)	C11—C10—S1	108.82 (16)
C5—C4—H4A	121.7	C9—C10—S1	123.28 (15)
C3—C4—H4A	121.7	C10—C11—N2	117.20 (19)
C4—C5—C6	121.64 (18)	C10—C11—H11A	121.4
C4—C5—C8	130.06 (18)	N2—C11—H11A	121.4
C6—C5—C8	108.28 (16)	N2—C12—S1	116.78 (16)
C1—C6—C5	121.80 (17)	N2—C12—Br1	123.85 (16)
C1—C6—C7	129.66 (18)	S1—C12—Br1	119.35 (12)
C6—C1—C2—C3	0.3 (3)	C9—N1—C8—O2	6.2 (3)
C1—C2—C3—C4	0.8 (3)	C7—N1—C8—C5	−0.3 (2)
C2—C3—C4—C5	−0.7 (3)	C9—N1—C8—C5	−173.38 (17)
C3—C4—C5—C6	−0.3 (3)	C4—C5—C8—O2	−1.4 (4)
C3—C4—C5—C8	−178.7 (2)	C6—C5—C8—O2	−179.9 (2)
C2—C1—C6—C5	−1.3 (3)	C4—C5—C8—N1	178.2 (2)
C2—C1—C6—C7	177.74 (19)	C6—C5—C8—N1	−0.4 (2)
C4—C5—C6—C1	1.4 (3)	C7—N1—C9—C10	−93.5 (2)
C8—C5—C6—C1	−179.93 (18)	C8—N1—C9—C10	78.9 (2)
C4—C5—C6—C7	−177.85 (18)	N1—C9—C10—C11	89.7 (2)
C8—C5—C6—C7	0.8 (2)	N1—C9—C10—S1	−87.1 (2)
C8—N1—C7—O1	−178.64 (19)	C12—S1—C10—C11	0.83 (15)
C9—N1—C7—O1	−5.6 (3)	C12—S1—C10—C9	178.21 (16)
C8—N1—C7—C6	0.8 (2)	C9—C10—C11—N2	−178.07 (18)
C9—N1—C7—C6	173.84 (17)	S1—C10—C11—N2	−0.8 (2)
C1—C6—C7—O1	−0.8 (4)	C12—N2—C11—C10	0.3 (3)
C5—C6—C7—O1	178.4 (2)	C11—N2—C12—S1	0.4 (2)
C1—C6—C7—N1	179.87 (19)	C11—N2—C12—Br1	−177.90 (14)
C5—C6—C7—N1	−1.0 (2)	C10—S1—C12—N2	−0.74 (17)
C7—N1—C8—O2	179.30 (19)	C10—S1—C12—Br1	177.63 (12)