DC133

Table 1 Crystal data and structure refinement for DC133.
Identification code	DC133
Empirical formula	C₁₁H₁₄O₃TiBr
Formula weight	309.07
Temperature/K	150.0
Crystal system	orthorhombic
Space group	Ccc2
a/Å	11.4688(12)
b/Å	22.418(2)
c/Å	10.6590(12)
α/°	90
β/°	90
γ/°	90
Volume/Å³	2740.5(5)
Z	8
ρ_calcmg/mm³	1.4981
m/mm^‑1	3.261
F(000)	1239.6
Crystal size/mm³	N/A × N/A × N/A
Radiation	Mo Kα (λ = 0.71073)
2Θ range for data collection	3.64 to 67.1°
Index ranges	-17 ≤ h ≤ 17, -34 ≤ k ≤ 22, -16 ≤ l ≤ 16
Reflections collected	19850
Independent reflections	5371 [R_int = 0.0238, R_sigma = 0.0410]
Data/restraints/parameters	5371/0/151
Goodness-of-fit on F²	0.964
Final R indexes [I>=2σ (I)]	R₁ = 0.0281, wR₂ = N/A
Final R indexes [all data]	R₁ = 0.0380, wR₂ = 0.0714
Largest diff. peak/hole / e Å^-3	1.09/-0.46
Flack parameter	0.016(7)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for DC133. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.
Atom	x	y	z	U(eq)
Br1	2149.0(2)	4970.04(8)	9611.39(18)	48.27(7)
Ti1	2500	7500	3142.8(3)	20.54(7)
O3	2380.4(8)	6881.5(5)	2035.1(12)	27.2(2)
O2	2219.9(9)	6912.5(5)	4634.8(12)	24.76(19)
O1	791.5(8)	7665.6(5)	3392.3(9)	25.5(2)
C10	2664.3(13)	6158.1(8)	6631.9(16)	28.9(3)
C9	2844.6(15)	5722.8(8)	7556.0(18)	33.5(3)
C8	1926.8(16)	5579.0(7)	8374.7(16)	35.7(4)
C5	1572.0(12)	6449.8(7)	6514.5(14)	24.7(3)
C1	-1087.3(14)	7879.8(10)	4222.8(18)	44.8(5)
C2	98.2(11)	7582.8(7)	4334.8(15)	26.2(3)
C3	368.7(14)	7234.6(8)	5397.2(16)	30.1(3)
C4	1404.0(12)	6890.4(6)	5465.7(13)	22.5(3)
C7	857.7(18)	5869.7(8)	8301.0(19)	47.5(4)
C6	680.5(16)	6308.2(8)	7374.5(17)	40.9(4)
C11	2540.9(17)	6264.1(9)	1859(2)	44.1(5)
C12	3800.3(18)	6062.3(9)	2051(3)	56.8(6)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for DC133. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.

Atom

U(eq)

Br1

2149.0(2)

4970.04(8)

9611.39(18)

48.27(7)

Ti1

2500

7500

3142.8(3)

20.54(7)

2380.4(8)

6881.5(5)

2035.1(12)

27.2(2)

2219.9(9)

6912.5(5)

4634.8(12)

24.76(19)

791.5(8)

7665.6(5)

3392.3(9)

25.5(2)

C10

2664.3(13)

6158.1(8)

6631.9(16)

28.9(3)

2844.6(15)

5722.8(8)

7556.0(18)

33.5(3)

1926.8(16)

5579.0(7)

8374.7(16)

35.7(4)

1572.0(12)

6449.8(7)

6514.5(14)

24.7(3)

-1087.3(14)

7879.8(10)

4222.8(18)

44.8(5)

98.2(11)

7582.8(7)

4334.8(15)

26.2(3)

368.7(14)

7234.6(8)

5397.2(16)

30.1(3)

1404.0(12)

6890.4(6)

5465.7(13)

22.5(3)

857.7(18)

5869.7(8)

8301.0(19)

47.5(4)

680.5(16)

6308.2(8)

7374.5(17)

40.9(4)

C11

2540.9(17)

6264.1(9)

1859(2)

44.1(5)

C12

3800.3(18)

6062.3(9)

2051(3)

56.8(6)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for DC133. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].
Atom	U₁₁	U₂₂	U₃₃	U₁₂	U₁₃	U₂₃
Br1	83.92(15)	28.98(9)	31.91(9)	-1.85(8)	-8.18(11)	7.86(8)
Ti1	17.09(11)	30.30(17)	14.23(13)	-2.27(12)	-0	0
O3	25.8(5)	32.7(6)	23.2(5)	-1.5(4)	-2.4(4)	-4.7(5)
O2	21.9(4)	31.3(5)	21.1(5)	-0.1(4)	2.7(4)	3.2(5)
O1	19.7(4)	38.2(5)	18.7(5)	-1.8(4)	-0.5(3)	3.1(4)
C10	32.1(8)	27.6(8)	27.1(8)	-1.7(5)	-1.8(6)	1.0(7)
C9	39.2(8)	27.9(8)	33.3(9)	0.4(6)	-8.3(7)	0.8(7)
C8	59.2(10)	24.7(7)	23.1(8)	-4.1(7)	-6.0(7)	1.8(6)
C5	29.6(7)	25.4(7)	19.2(6)	-4.0(5)	0.1(5)	-0.6(6)
C1	29.7(8)	69.6(13)	35.0(9)	15.2(8)	8.1(7)	14.4(9)
C2	20.4(5)	34.5(8)	23.8(8)	-0.1(5)	1.8(5)	1.1(6)
C3	27.8(6)	41.0(9)	21.5(7)	4.1(6)	6.6(6)	5.4(7)
C4	25.1(6)	25.3(7)	17.0(6)	-2.2(5)	-0.2(5)	-0.9(5)
C7	57.6(10)	45.2(10)	39.6(11)	0.4(8)	14.9(9)	16.8(9)
C6	39.2(9)	44.3(10)	39.1(10)	3.9(7)	12.0(8)	15.5(8)
C11	41.5(9)	33.0(9)	58.0(14)	-5.8(7)	-6.8(9)	-3.4(9)
C12	45(1)	36.2(9)	89.1(18)	6.9(8)	-7.4(12)	-5.4(12)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for DC133. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].

Atom

U₁₁

U₂₂

U₃₃

U₁₂

U₁₃

U₂₃

Br1

83.92(15)

28.98(9)

31.91(9)

-1.85(8)

-8.18(11)

7.86(8)

Ti1

17.09(11)

30.30(17)

14.23(13)

-2.27(12)

-0

25.8(5)

32.7(6)

23.2(5)

-1.5(4)

-2.4(4)

-4.7(5)

21.9(4)

31.3(5)

21.1(5)

-0.1(4)

2.7(4)

3.2(5)

19.7(4)

38.2(5)

18.7(5)

-1.8(4)

-0.5(3)

3.1(4)

C10

32.1(8)

27.6(8)

27.1(8)

-1.7(5)

-1.8(6)

1.0(7)

39.2(8)

27.9(8)

33.3(9)

0.4(6)

-8.3(7)

0.8(7)

59.2(10)

24.7(7)

23.1(8)

-4.1(7)

-6.0(7)

1.8(6)

29.6(7)

25.4(7)

19.2(6)

-4.0(5)

0.1(5)

-0.6(6)

29.7(8)

69.6(13)

35.0(9)

15.2(8)

8.1(7)

14.4(9)

20.4(5)

34.5(8)

23.8(8)

-0.1(5)

1.8(5)

1.1(6)

27.8(6)

41.0(9)

21.5(7)

4.1(6)

6.6(6)

5.4(7)

25.1(6)

25.3(7)

17.0(6)

-2.2(5)

-0.2(5)

-0.9(5)

57.6(10)

45.2(10)

39.6(11)

0.4(8)

14.9(9)

16.8(9)

39.2(9)

44.3(10)

39.1(10)

3.9(7)

12.0(8)

15.5(8)

C11

41.5(9)

33.0(9)

58.0(14)

-5.8(7)

-6.8(9)

-3.4(9)

C12

45(1)

36.2(9)

89.1(18)

6.9(8)

-7.4(12)

-5.4(12)

Table 4 Bond Lengths for DC133.
Atom	Atom	Length/Å	Atom	Atom	Length/Å
Br1	C8	1.9148(17)	C10	C5	1.419(2)
Ti1	O3	1.8264(12)	C9	C8	1.405(3)
Ti1	O3¹	1.8264(12)	C8	C7	1.391(3)
Ti1	O2¹	2.0897(12)	C5	C4	1.504(2)
Ti1	O2	2.0897(12)	C5	C6	1.409(2)
Ti1	O1	2.0119(9)	C1	C2	1.519(2)
Ti1	O1¹	2.0119(9)	C2	C3	1.410(2)
O3	C11	1.409(2)	C3	C4	1.418(2)
O2	C4	1.2894(18)	C7	C6	1.408(2)
O1	C2	1.2946(17)	C11	C12	1.527(3)
C10	C9	1.402(3)

Table 4 Bond Lengths for DC133.

Atom

Length/Å

Atom

Length/Å

Br1

1.9148(17)

C10

1.419(2)

Ti1

1.8264(12)

1.405(3)

Ti1

O3¹

1.8264(12)

1.391(3)

Ti1

O2¹

2.0897(12)

1.504(2)

Ti1

2.0897(12)

1.409(2)

Ti1

2.0119(9)

1.519(2)

Ti1

O1¹

2.0119(9)

1.410(2)

C11

1.409(2)

1.418(2)

1.2894(18)

1.408(2)

1.2946(17)

C11

C12

1.527(3)

C10

1.402(3)

Table 5 Bond Angles for DC133.
Atom	Atom	Atom	Angle/˚	Atom	Atom	Atom	Angle/˚
O3¹	Ti1	O3	99.44(8)	C5	C10	C9	120.87(15)
O2	Ti1	O3	90.11(5)	C8	C9	C10	119.06(16)
O2	Ti1	O3¹	169.12(5)	C9	C8	Br1	119.45(14)
O2¹	Ti1	O3	169.12(5)	C7	C8	Br1	119.36(14)
O2¹	Ti1	O3¹	90.11(5)	C7	C8	C9	121.19(17)
O2¹	Ti1	O2	80.89(7)	C4	C5	C10	118.78(13)
O1	Ti1	O3¹	91.06(4)	C6	C5	C10	118.65(14)
O1	Ti1	O3	98.77(4)	C6	C5	C4	122.57(13)
O1¹	Ti1	O3¹	98.77(4)	C1	C2	O1	115.22(14)
O1¹	Ti1	O3	91.06(4)	C3	C2	O1	124.58(13)
O1	Ti1	O2	82.30(4)	C3	C2	C1	120.19(14)
O1	Ti1	O2¹	86.15(4)	C4	C3	C2	121.79(14)
O1¹	Ti1	O2	86.15(4)	C5	C4	O2	116.28(12)
O1¹	Ti1	O2¹	82.30(4)	C3	C4	O2	123.47(14)
O1¹	Ti1	O1	164.81(6)	C3	C4	C5	120.19(13)
C11	O3	Ti1	145.30(14)	C6	C7	C8	119.60(16)
C4	O2	Ti1	131.18(9)	C7	C6	C5	120.58(16)
C2	O1	Ti1	132.40(9)	C12	C11	O3	113.37(16)

Table 5 Bond Angles for DC133.

Atom

Angle/˚

Atom

Angle/˚

O3¹

Ti1

99.44(8)

C10

120.87(15)

Ti1

90.11(5)

C10

119.06(16)

Ti1

O3¹

169.12(5)

Br1

119.45(14)

O2¹

Ti1

169.12(5)

Br1

119.36(14)

O2¹

Ti1

O3¹

90.11(5)

121.19(17)

O2¹

Ti1

80.89(7)

C10

118.78(13)

Ti1

O3¹

91.06(4)

C10

118.65(14)

Ti1

98.77(4)

122.57(13)

O1¹

Ti1

O3¹

98.77(4)

115.22(14)

O1¹

Ti1

91.06(4)

124.58(13)

Ti1

82.30(4)

120.19(14)

Ti1

O2¹

86.15(4)

121.79(14)

O1¹

Ti1

86.15(4)

116.28(12)

O1¹

Ti1

O2¹

82.30(4)

123.47(14)

O1¹

Ti1

164.81(6)

120.19(13)

C11

Ti1

145.30(14)

119.60(16)

Ti1

131.18(9)

120.58(16)

Ti1

132.40(9)

C12

C11

113.37(16)

Table 6 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for DC133.
Atom	x	y	z	U(eq)
H10	3281.7(13)	6259.1(8)	6077.0(16)	34.7(4)
H9	3577.1(15)	5527.9(8)	7627.6(18)	40.2(4)
H1a	-986.5(17)	8313.3(11)	4174(16)	67.1(7)
H1b	-1480(6)	7737(6)	3463(9)	67.1(7)
H1c	-1561(6)	7781(6)	4959(8)	67.1(7)
H3	-157.1(14)	7230.3(8)	6085.8(16)	36.1(4)
H7	250.6(18)	5773.1(8)	8872.3(19)	57.0(5)
H6	-46.3(16)	6510.4(8)	7328.7(17)	49.0(5)
H11a	2033.4(17)	6045.7(9)	2454(2)	53.0(6)
H11b	2293.0(17)	6157.1(9)	998(2)	53.0(6)
H12a	4319(2)	6304(5)	1525(12)	85.2(9)
H12b	4016(5)	6112(7)	2934(4)	85.2(9)
H12c	3875(4)	5641(2)	1816(15)	85.2(9)

Table 6 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for DC133.

Atom

U(eq)

H10

3281.7(13)

6259.1(8)

6077.0(16)

34.7(4)

3577.1(15)

5527.9(8)

7627.6(18)

40.2(4)

H1a

-986.5(17)

8313.3(11)

4174(16)

67.1(7)

H1b

-1480(6)

7737(6)

3463(9)

67.1(7)

H1c

-1561(6)

7781(6)

4959(8)

67.1(7)

-157.1(14)

7230.3(8)

6085.8(16)

36.1(4)

250.6(18)

5773.1(8)

8872.3(19)

57.0(5)

-46.3(16)

6510.4(8)

7328.7(17)

49.0(5)

H11a

2033.4(17)

6045.7(9)

2454(2)

53.0(6)

H11b

2293.0(17)

6157.1(9)

998(2)

53.0(6)

H12a

4319(2)

6304(5)

1525(12)

85.2(9)

H12b

4016(5)

6112(7)

2934(4)

85.2(9)

H12c

3875(4)

5641(2)

1816(15)

85.2(9)

Experimental

Single crystals of C₁₁H₁₄O₃TiBr [DC133] were [?]. A suitable crystal was selected and [MiTeGen crystal mount] on a Bruker X8 diffractometer. The crystal was kept at 150.0 K during data collection. Using Olex2 [1], the structure was solved with the Superflip [2] structure solution program using Charge Flipping and refined with the olex2.refine [3] refinement package using Gauss-Newton minimisation.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341.
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790; Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984; Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45, 575-580
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H. (2013). in preparation

Crystal structure determination of [DC133]

Crystal Data for C₁₁H₁₄O₃TiBr (M =309.07): orthorhombic, space group Ccc2 (no. 37), a = 11.4688(12) Å, b = 22.418(2) Å, c = 10.6590(12) Å, V = 2740.5(5) Å³, Z = 8, T = 150.0 K, μ(Mo Kα) = 3.261 mm^-1, Dcalc = 1.4981 g/mm³, 19850 reflections measured (3.64 ≤ 2Θ ≤ 67.1), 5371 unique (R_int = 0.0238, R_sigma = 0.0410) which were used in all calculations. The final R₁ was 0.0281 (I>=2u(I)) and wR₂ was 0.0714 (all data).

Refinement model description

Number of restraints - 0, number of constraints - 21.

Details:

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C3(H3), C7(H7), C6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C12(H12a,H12b,H12c)

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