bilm001

Table 1 Crystal data and structure refinement for bilm001.
Identification code	bilm001
Empirical formula	C₁₈H₁₉NO
Formula weight	265.34
Temperature/K	120
Crystal system	orthorhombic
Space group	P2₁2₁2₁
a/Å	6.9787(4)
b/Å	12.4957(8)
c/Å	16.1330(11)
α/°	90
β/°	90
γ/°	90
Volume/Å³	1406.86(15)
Z	4
ρ_calcg/cm³	1.253
μ/mm^‑1	0.599
F(000)	568.0
Crystal size/mm³	0.214 × 0.08 × 0.059
Radiation	Cu Kα (λ = 1.54178)
2Θ range for data collection/°	8.952 to 150.53
Index ranges	-7 ≤ h ≤ 8, -15 ≤ k ≤ 15, -19 ≤ l ≤ 20
Reflections collected	10188
Independent reflections	2889 [R_int = 0.0246, R_sigma = 0.0245]
Data/restraints/parameters	2889/0/257
Goodness-of-fit on F²	1.067
Final R indexes [I>=2σ (I)]	R₁ = 0.0288, wR₂ = 0.0728
Final R indexes [all data]	R₁ = 0.0301, wR₂ = 0.0738
Largest diff. peak/hole / e Å^-3	0.17/-0.16
Flack parameter	0.03(10)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for bilm001. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.
Atom	x	y	z	U(eq)
O1	6218.2(18)	3236.5(9)	6090.6(8)	27.9(3)
N1	6467(2)	4260.8(11)	4936.3(8)	22.5(3)
C1	5903(2)	4088.3(12)	5740.3(10)	21.0(3)
C2	4967(2)	5028.5(12)	6179.4(10)	19.3(3)
C3	3631(2)	5613.3(12)	5575.2(9)	20.6(3)
C4	4748(2)	5949.5(13)	4825.8(10)	21.2(3)
C5	4411(2)	6910.3(13)	4414.5(11)	25.9(4)
C6	5405(3)	7167.8(14)	3694.3(11)	27.2(4)
C7	6770(3)	6465.2(14)	3391.0(11)	26.1(4)
C8	7165(2)	5510.5(13)	3803.5(11)	24.2(4)
C9	6146(2)	5247.9(12)	4519.9(10)	21.1(3)
C10	6530(2)	5773.4(13)	6541.6(10)	23.0(3)
C11	5470(3)	6424.8(13)	7203.8(11)	26.4(4)
C12	3836(3)	5709.7(13)	7483.5(10)	24.3(3)
C13	3857(2)	4692.6(12)	6957.1(10)	21.3(3)
C14	1917(2)	4223.9(14)	6778.5(11)	25.2(4)
C15	1074(2)	4307.2(14)	6049.3(11)	26.9(4)
C16	1926(2)	4895.4(15)	5328.1(11)	26.1(4)
C17	7439(3)	3391.8(14)	4491.9(12)	30.5(4)
C18	2561(3)	5934.7(16)	8065.7(12)	34.6(4)

Table 2 Fractional Atomic Coordinates (×10⁴) and Equivalent Isotropic Displacement Parameters (Å²×10³) for bilm001. U_eq is defined as 1/3 of of the trace of the orthogonalised U_IJ tensor.

Atom

U(eq)

6218.2(18)

3236.5(9)

6090.6(8)

27.9(3)

6467(2)

4260.8(11)

4936.3(8)

22.5(3)

5903(2)

4088.3(12)

5740.3(10)

21.0(3)

4967(2)

5028.5(12)

6179.4(10)

19.3(3)

3631(2)

5613.3(12)

5575.2(9)

20.6(3)

4748(2)

5949.5(13)

4825.8(10)

21.2(3)

4411(2)

6910.3(13)

4414.5(11)

25.9(4)

5405(3)

7167.8(14)

3694.3(11)

27.2(4)

6770(3)

6465.2(14)

3391.0(11)

26.1(4)

7165(2)

5510.5(13)

3803.5(11)

24.2(4)

6146(2)

5247.9(12)

4519.9(10)

21.1(3)

C10

6530(2)

5773.4(13)

6541.6(10)

23.0(3)

C11

5470(3)

6424.8(13)

7203.8(11)

26.4(4)

C12

3836(3)

5709.7(13)

7483.5(10)

24.3(3)

C13

3857(2)

4692.6(12)

6957.1(10)

21.3(3)

C14

1917(2)

4223.9(14)

6778.5(11)

25.2(4)

C15

1074(2)

4307.2(14)

6049.3(11)

26.9(4)

C16

1926(2)

4895.4(15)

5328.1(11)

26.1(4)

C17

7439(3)

3391.8(14)

4491.9(12)

30.5(4)

C18

2561(3)

5934.7(16)

8065.7(12)

34.6(4)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for bilm001. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].
Atom	U₁₁	U₂₂	U₃₃	U₂₃	U₁₃	U₁₂
O1	27.9(6)	21.1(5)	34.7(7)	4.6(5)	2.2(5)	4.4(5)
N1	22.1(7)	20.1(6)	25.2(7)	-2.0(5)	1.1(6)	3.3(5)
C1	16.2(7)	20.1(7)	26.7(8)	-0.8(6)	-2.7(6)	-0.4(6)
C2	17.9(7)	19.2(7)	20.8(7)	1.0(6)	-1.3(6)	-1.2(6)
C3	20.8(7)	20.9(7)	20.2(7)	-0.1(6)	-1.4(7)	4.1(6)
C4	20.5(8)	23.4(7)	19.9(7)	-0.5(6)	-3.2(6)	1.0(6)
C5	28.1(9)	26.2(8)	23.6(8)	0.6(7)	-2.5(7)	4.7(7)
C6	29.6(9)	27.1(8)	24.8(8)	3.9(7)	-5.8(7)	-0.8(7)
C7	25.1(9)	32.0(8)	21.2(8)	0.4(7)	-0.1(7)	-4.8(7)
C8	21.6(8)	26.8(8)	24.4(8)	-3.9(7)	-0.3(7)	-0.1(6)
C9	21.0(8)	21.3(7)	21.0(7)	-2.8(6)	-3.5(7)	-1.8(6)
C10	22.6(8)	22.1(7)	24.3(8)	2.5(6)	-2.6(7)	-4.3(7)
C11	32.4(9)	22.8(8)	24.1(8)	-1.4(6)	-3.9(7)	-3.5(7)
C12	30.5(8)	22.8(7)	19.7(7)	1.1(6)	-5.9(7)	-1.0(7)
C13	23.6(8)	20.0(7)	20.4(7)	1.3(6)	1.3(7)	0.9(6)
C14	23.4(8)	23.7(8)	28.4(8)	-2.4(7)	6.7(7)	-2.6(7)
C15	17.8(8)	30.8(8)	32.1(9)	-7.2(7)	3.0(7)	-1.5(7)
C16	19.9(8)	32.9(9)	25.5(8)	-1.9(7)	-3.2(7)	-0.1(7)
C17	36.6(11)	23.8(8)	31.1(10)	-3.8(7)	4.9(8)	6.8(7)
C18	44.9(11)	32.6(9)	26.3(9)	-6.6(8)	5.2(8)	-6.2(8)

Table 3 Anisotropic Displacement Parameters (Å²×10³) for bilm001. The Anisotropic displacement factor exponent takes the form: -2π²[h²a*²U₁₁+2hka*b*U₁₂+…].

Atom

U₁₁

U₂₂

U₃₃

U₂₃

U₁₃

U₁₂

27.9(6)

21.1(5)

34.7(7)

4.6(5)

2.2(5)

4.4(5)

22.1(7)

20.1(6)

25.2(7)

-2.0(5)

1.1(6)

3.3(5)

16.2(7)

20.1(7)

26.7(8)

-0.8(6)

-2.7(6)

-0.4(6)

17.9(7)

19.2(7)

20.8(7)

1.0(6)

-1.3(6)

-1.2(6)

20.8(7)

20.9(7)

20.2(7)

-0.1(6)

-1.4(7)

4.1(6)

20.5(8)

23.4(7)

19.9(7)

-0.5(6)

-3.2(6)

1.0(6)

28.1(9)

26.2(8)

23.6(8)

0.6(7)

-2.5(7)

4.7(7)

29.6(9)

27.1(8)

24.8(8)

3.9(7)

-5.8(7)

-0.8(7)

25.1(9)

32.0(8)

21.2(8)

0.4(7)

-0.1(7)

-4.8(7)

21.6(8)

26.8(8)

24.4(8)

-3.9(7)

-0.3(7)

-0.1(6)

21.0(8)

21.3(7)

21.0(7)

-2.8(6)

-3.5(7)

-1.8(6)

C10

22.6(8)

22.1(7)

24.3(8)

2.5(6)

-2.6(7)

-4.3(7)

C11

32.4(9)

22.8(8)

24.1(8)

-1.4(6)

-3.9(7)

-3.5(7)

C12

30.5(8)

22.8(7)

19.7(7)

1.1(6)

-5.9(7)

-1.0(7)

C13

23.6(8)

20.0(7)

20.4(7)

1.3(6)

1.3(7)

0.9(6)

C14

23.4(8)

23.7(8)

28.4(8)

-2.4(7)

6.7(7)

-2.6(7)

C15

17.8(8)

30.8(8)

32.1(9)

-7.2(7)

3.0(7)

-1.5(7)

C16

19.9(8)

32.9(9)

25.5(8)

-1.9(7)

-3.2(7)

-0.1(7)

C17

36.6(11)

23.8(8)

31.1(10)

-3.8(7)

4.9(8)

6.8(7)

C18

44.9(11)

32.6(9)

26.3(9)

-6.6(8)

5.2(8)

-6.2(8)

Table 4 Bond Lengths for bilm001.
Atom	Atom	Length/Å	Atom	Atom	Length/Å
O1	C1	1.225(2)	C5	C6	1.391(3)
N1	C1	1.373(2)	C6	C7	1.385(3)
N1	C9	1.422(2)	C7	C8	1.394(2)
N1	C17	1.468(2)	C8	C9	1.396(2)
C1	C2	1.519(2)	C10	C11	1.533(2)
C2	C3	1.534(2)	C11	C12	1.518(2)
C2	C10	1.549(2)	C12	C13	1.528(2)
C2	C13	1.533(2)	C12	C18	1.324(3)
C3	C4	1.499(2)	C13	C14	1.503(2)
C3	C16	1.542(2)	C14	C15	1.319(3)
C4	C5	1.392(2)	C15	C16	1.499(2)
C4	C9	1.401(2)

Table 4 Bond Lengths for bilm001.

Atom

Length/Å

Atom

Length/Å

1.225(2)

1.391(3)

1.373(2)

1.385(3)

1.422(2)

1.394(2)

C17

1.468(2)

1.396(2)

1.519(2)

C10

C11

1.533(2)

1.534(2)

C11

C12

1.518(2)

C10

1.549(2)

C12

C13

1.528(2)

C13

1.533(2)

C12

C18

1.324(3)

1.499(2)

C13

C14

1.503(2)

C16

1.542(2)

C14

C15

1.319(3)

1.392(2)

C15

C16

1.499(2)

1.401(2)

Table 5 Bond Angles for bilm001.
Atom	Atom	Atom	Angle/˚	Atom	Atom	Atom	Angle/˚
C1	N1	C9	122.50(13)	C6	C5	C4	120.87(16)
C1	N1	C17	118.56(14)	C7	C6	C5	119.45(16)
C9	N1	C17	118.94(14)	C6	C7	C8	120.67(16)
O1	C1	N1	121.39(15)	C7	C8	C9	119.72(16)
O1	C1	C2	122.28(15)	C4	C9	N1	119.08(14)
N1	C1	C2	116.26(13)	C8	C9	N1	120.96(14)
C1	C2	C3	109.48(13)	C8	C9	C4	119.93(14)
C1	C2	C10	109.76(13)	C11	C10	C2	104.02(13)
C1	C2	C13	112.77(13)	C12	C11	C10	104.90(13)
C3	C2	C10	112.43(12)	C11	C12	C13	108.49(14)
C13	C2	C3	110.07(13)	C18	C12	C11	126.22(16)
C13	C2	C10	102.22(12)	C18	C12	C13	125.26(16)
C2	C3	C16	110.86(13)	C12	C13	C2	103.41(12)
C4	C3	C2	109.25(13)	C14	C13	C2	113.88(13)
C4	C3	C16	110.85(13)	C14	C13	C12	114.95(14)
C5	C4	C3	122.56(15)	C15	C14	C13	122.81(16)
C5	C4	C9	119.32(15)	C14	C15	C16	123.63(16)
C9	C4	C3	118.09(14)	C15	C16	C3	112.98(14)

Table 5 Bond Angles for bilm001.

Atom

Angle/˚

Atom

Angle/˚

122.50(13)

120.87(16)

C17

118.56(14)

119.45(16)

C17

118.94(14)

120.67(16)

121.39(15)

119.72(16)

122.28(15)

119.08(14)

116.26(13)

120.96(14)

109.48(13)

119.93(14)

C10

109.76(13)

C11

C10

104.02(13)

C13

112.77(13)

C12

C11

C10

104.90(13)

C10

112.43(12)

C11

C12

C13

108.49(14)

C13

110.07(13)

C18

C12

C11

126.22(16)

C13

C10

102.22(12)

C18

C12

C13

125.26(16)

C16

110.86(13)

C12

C13

103.41(12)

109.25(13)

C14

C13

113.88(13)

C16

110.85(13)

C14

C13

C12

114.95(14)

122.56(15)

C15

C14

C13

122.81(16)

119.32(15)

C14

C15

C16

123.63(16)

118.09(14)

C15

C16

112.98(14)

Table 6 Torsion Angles for bilm001.
A	B	C	D	Angle/˚	A	B	C	D	Angle/˚
O1	C1	C2	C3	-143.18(15)	C6	C7	C8	C9	1.4(2)
O1	C1	C2	C10	92.97(18)	C7	C8	C9	N1	177.61(15)
O1	C1	C2	C13	-20.3(2)	C7	C8	C9	C4	-0.7(2)
N1	C1	C2	C3	39.93(18)	C9	N1	C1	O1	-178.97(15)
N1	C1	C2	C10	-83.92(16)	C9	N1	C1	C2	-2.1(2)
N1	C1	C2	C13	162.83(14)	C9	C4	C5	C6	1.7(2)
C1	N1	C9	C4	-19.4(2)	C10	C2	C3	C4	65.89(16)
C1	N1	C9	C8	162.28(15)	C10	C2	C3	C16	-171.67(13)
C1	C2	C3	C4	-56.38(16)	C10	C2	C13	C12	37.75(15)
C1	C2	C3	C16	66.06(16)	C10	C2	C13	C14	163.19(13)
C1	C2	C10	C11	-160.51(13)	C10	C11	C12	C13	-3.61(17)
C1	C2	C13	C12	155.52(13)	C10	C11	C12	C18	178.37(18)
C1	C2	C13	C14	-79.03(16)	C11	C12	C13	C2	-21.59(17)
C2	C3	C4	C5	-143.46(15)	C11	C12	C13	C14	-146.34(15)
C2	C3	C4	C9	38.42(19)	C12	C13	C14	C15	104.97(18)
C2	C3	C16	C15	43.45(19)	C13	C2	C3	C4	179.13(13)
C2	C10	C11	C12	27.25(16)	C13	C2	C3	C16	-58.43(17)
C2	C13	C14	C15	-14.1(2)	C13	C2	C10	C11	-40.60(15)
C3	C2	C10	C11	77.38(16)	C13	C14	C15	C16	-1.5(3)
C3	C2	C13	C12	-81.91(15)	C14	C15	C16	C3	-13.7(2)
C3	C2	C13	C14	43.54(17)	C16	C3	C4	C5	94.10(18)
C3	C4	C5	C6	-176.42(16)	C16	C3	C4	C9	-84.03(17)
C3	C4	C9	N1	-1.0(2)	C17	N1	C1	O1	1.0(2)
C3	C4	C9	C8	177.39(14)	C17	N1	C1	C2	177.90(14)
C4	C3	C16	C15	164.96(14)	C17	N1	C9	C4	160.68(15)
C4	C5	C6	C7	-1.0(3)	C17	N1	C9	C8	-17.7(2)
C5	C4	C9	N1	-179.17(15)	C18	C12	C13	C2	156.45(17)
C5	C4	C9	C8	-0.8(2)	C18	C12	C13	C14	31.7(2)
C5	C6	C7	C8	-0.6(3)

Table 6 Torsion Angles for bilm001.

Angle/˚

-143.18(15)

1.4(2)

C10

92.97(18)

177.61(15)

C13

-20.3(2)

-0.7(2)

39.93(18)

-178.97(15)

C10

-83.92(16)

-2.1(2)

C13

162.83(14)

1.7(2)

-19.4(2)

C10

65.89(16)

162.28(15)

C10

C16

-171.67(13)

-56.38(16)

C10

C13

C12

37.75(15)

C16

66.06(16)

C10

C13

C14

163.19(13)

C10

C11

-160.51(13)

C10

C11

C12

C13

-3.61(17)

C13

C12

155.52(13)

C10

C11

C12

C18

178.37(18)

C13

C14

-79.03(16)

C11

C12

C13

-21.59(17)

-143.46(15)

C11

C12

C13

C14

-146.34(15)

38.42(19)

C12

C13

C14

C15

104.97(18)

C16

C15

43.45(19)

C13

179.13(13)

C10

C11

C12

27.25(16)

C13

C16

-58.43(17)

C13

C14

C15

-14.1(2)

C13

C10

C11

-40.60(15)

C10

C11

77.38(16)

C13

C14

C15

C16

-1.5(3)

C13

C12

-81.91(15)

C14

C15

C16

-13.7(2)

C13

C14

43.54(17)

C16

94.10(18)

-176.42(16)

C16

-84.03(17)

-1.0(2)

C17

1.0(2)

177.39(14)

C17

177.90(14)

C16

C15

164.96(14)

C17

160.68(15)

-1.0(3)

C17

-17.7(2)

-179.17(15)

C18

C12

C13

156.45(17)

-0.8(2)

C18

C12

C13

C14

31.7(2)

-0.6(3)

Table 7 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for bilm001.
Atom	x	y	z	U(eq)
H3	3150(30)	6244(15)	5867(11)	19(5)
H5	3440(30)	7394(16)	4637(12)	25(5)
H6	5160(30)	7846(18)	3414(14)	36(6)
H7	7460(30)	6583(16)	2881(12)	23(5)
H8	8150(30)	5020(18)	3598(13)	33(6)
H10A	7170(30)	6211(17)	6124(14)	31(5)
H10B	7570(30)	5306(16)	6785(12)	22(5)
H11A	6330(30)	6643(16)	7679(13)	30(5)
H11B	4920(30)	7092(16)	6946(13)	28(5)
H13	4630(30)	4157(16)	7245(12)	23(5)
H14	1280(30)	3832(16)	7237(13)	37(6)
H15	-200(30)	3959(18)	5955(13)	39(6)
H16A	2340(30)	4371(16)	4900(12)	25(5)
H16B	960(30)	5368(18)	5061(14)	40(6)
H17A	8770(40)	3573(17)	4363(14)	38(6)
H17B	7390(40)	2766(19)	4832(15)	41(7)
H17C	6780(40)	3261(19)	3957(16)	47(7)
H18A	1500(40)	5415(18)	8200(14)	39(6)
H18B	2630(30)	6607(19)	8371(14)	38(6)

Table 7 Hydrogen Atom Coordinates (Å×10⁴) and Isotropic Displacement Parameters (Å²×10³) for bilm001.

Atom

U(eq)

3150(30)

6244(15)

5867(11)

19(5)

3440(30)

7394(16)

4637(12)

25(5)

5160(30)

7846(18)

3414(14)

36(6)

7460(30)

6583(16)

2881(12)

23(5)

8150(30)

5020(18)

3598(13)

33(6)

H10A

7170(30)

6211(17)

6124(14)

31(5)

H10B

7570(30)

5306(16)

6785(12)

22(5)

H11A

6330(30)

6643(16)

7679(13)

30(5)

H11B

4920(30)

7092(16)

6946(13)

28(5)

H13

4630(30)

4157(16)

7245(12)

23(5)

H14

1280(30)

3832(16)

7237(13)

37(6)

H15

-200(30)

3959(18)

5955(13)

39(6)

H16A

2340(30)

4371(16)

4900(12)

25(5)

H16B

960(30)

5368(18)

5061(14)

40(6)

H17A

8770(40)

3573(17)

4363(14)

38(6)

H17B

7390(40)

2766(19)

4832(15)

41(7)

H17C

6780(40)

3261(19)

3957(16)

47(7)

H18A

1500(40)

5415(18)

8200(14)

39(6)

H18B

2630(30)

6607(19)

8371(14)

38(6)

Experimental

Single crystals of C₁₈H₁₉NO [bilm001] were [Slow evaporation of solution in acetonitrile/hexanes.]. A suitable crystal was selected and [Mounted with alkane oil on plastic mesh.] on a Bruker APEX-II CCD diffractometer. The crystal was kept at 120 K during data collection. Using Olex2 [1], the structure was solved with the SHELXT [2] structure solution program using Intrinsic Phasing and refined with the XL [3] refinement package using Least Squares minimisation.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341.
Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Crystal structure determination of [bilm001]

Crystal Data for C₁₈H₁₉NO (M =265.34 g/mol): orthorhombic, space group P2₁2₁2₁ (no. 19), a = 6.9787(4) Å, b = 12.4957(8) Å, c = 16.1330(11) Å, V = 1406.86(15) Å³, Z = 4, T = 120 K, μ(Cu Kα) = 0.599 mm^-1, Dcalc = 1.253 g/cm³, 10188 reflections measured (8.952° ≤ 2Θ ≤ 150.53°), 2889 unique (R_int = 0.0246, R_sigma = 0.0245) which were used in all calculations. The final R₁ was 0.0288 (I > 2σ(I)) and wR₂ was 0.0738 (all data).

Refinement model description

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

Details:

N/A

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