marc

Crystal Structure Report for marc

A specimen of C₁₇H₂₀O₄, approximate dimensions 0.440 mm x 0.557 mm x 0.600 mm, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured.

The total exposure time was 0.67 hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data using a monoclinic unit cell yielded a total of 9710 reflections to a maximum θ angle of 27.65° (0.77 Å resolution), of which 3528 were independent (average redundancy 2.752, completeness = 98.6%, R_int = 2.54%) and 2872 (81.41%) were greater than 2σ(F²). The final cell constants of a = 24.445(7) Å, b = 7.241(2) Å, c = 17.657(5) Å, β = 101.424(4)°, volume = 3063.5(16) Å³, are based upon the refinement of the XYZ-centroids of 2803 reflections above 20 σ(I) with 4.707° < 2θ < 55.16°. Data were corrected for absorption effects using the multi-scan method (SADABS). The ratio of minimum to maximum apparent transmission was 0.924. The calculated minimum and maximum transmission coefficients (based on crystal size) are 0.6892 and 0.7456.

The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group C 1 2/c 1, with Z = 8 for the formula unit, C₁₇H₂₀O₄. The final anisotropic full-matrix least-squares refinement on F² with 194 variables converged at R1 = 4.51%, for the observed data and wR2 = 12.83% for all data. The goodness-of-fit was 1.039. The largest peak in the final difference electron density synthesis was 0.343 e^-/Å³ and the largest hole was -0.276 e^-/Å³ with an RMS deviation of 0.046 e^-/Å³. On the basis of the final model, the calculated density was 1.250 g/cm³ and F(000), 1232 e^-.

Table 1. Sample and crystal data for marc.

Identification code	marc
Chemical formula	C₁₇H₂₀O₄
Formula weight	288.33
Temperature	200(2) K
Wavelength	0.71073 Å
Crystal size	0.440 x 0.557 x 0.600 mm
Crystal system	monoclinic
Space group	C 1 2/c 1
Unit cell dimensions	a = 24.445(7) Å	α = 90°
	b = 7.241(2) Å	β = 101.424(4)°
	c = 17.657(5) Å	γ = 90°
Volume	3063.5(16) Å³
Z	8
Density (calculated)	1.250 g/cm³
Absorption coefficient	0.088 mm^-1
F(000)	1232

Table 2. Data collection and structure refinement for marc.

Theta range for data collection	2.35 to 27.65°
Index ranges	-29<=h<=31, -9<=k<=9, -22<=l<=23
Reflections collected	9710
Independent reflections	3528 [R(int) = 0.0254]
Coverage of independent reflections	98.6%
Absorption correction	multi-scan
Max. and min. transmission	0.7456 and 0.6892
Structure solution technique	direct methods
Structure solution program	SHELXS-97 (Sheldrick, 2008)
Refinement method	Full-matrix least-squares on F²
Refinement program	SHELXL-2013 (Sheldrick, 2013)
Function minimized	Σ w(F_o² - F_c²)²
Data / restraints / parameters	3528 / 0 / 194
Goodness-of-fit on F²	1.039
Δ/σ_max	0.005
Final R indices	2872 data; I>2σ(I)	R1 = 0.0451, wR2 = 0.1208
	all data	R1 = 0.0551, wR2 = 0.1283
Weighting scheme	w=1/[σ²(F_o²)+(0.0706P)²+1.5021P] where P=(F_o²+2F_c²)/3
Largest diff. peak and hole	0.343 and -0.276 eÅ^-3
R.M.S. deviation from mean	0.046 eÅ^-3

Table 3. Atomic coordinates and equivalent isotropic atomic displacement parameters (Å²) for marc.

U(eq) is defined as one third of the trace of the orthogonalized U_ij tensor.

	x/a	y/b	z/c	U(eq)
O1	0.20309(4)	0.55874(15)	0.91532(7)	0.0371(3)
O2	0.11487(4)	0.55656(13)	0.84808(5)	0.0256(2)
O3	0.06489(4)	0.51542(14)	0.00077(6)	0.0324(3)
O4	0.97745(4)	0.77046(14)	0.92759(6)	0.0296(3)
C1	0.12121(5)	0.93410(17)	0.93137(7)	0.0202(3)
C2	0.13223(5)	0.72922(17)	0.96465(7)	0.0198(3)
C3	0.07410(5)	0.65972(18)	0.96945(7)	0.0211(3)
C4	0.03314(5)	0.79458(18)	0.93380(7)	0.0212(3)
C5	0.05775(5)	0.94453(18)	0.91078(8)	0.0218(3)
C6	0.11939(6)	0.93561(19)	0.78593(8)	0.0291(3)
C7	0.14499(8)	0.9573(2)	0.72285(10)	0.0392(4)
C8	0.20015(8)	0.0118(3)	0.73383(10)	0.0445(4)
C9	0.22954(7)	0.0436(3)	0.80795(11)	0.0428(4)
C10	0.20402(6)	0.0221(2)	0.87116(9)	0.0317(3)
C11	0.14840(6)	0.96691(17)	0.86107(8)	0.0226(3)
C12	0.14100(6)	0.0817(2)	0.99373(9)	0.0304(3)
C13	0.15511(5)	0.60549(17)	0.90770(8)	0.0222(3)
C14	0.13303(7)	0.4626(2)	0.78437(9)	0.0351(4)
C15	0.08354(9)	0.4470(3)	0.71948(10)	0.0461(4)
C16	0.17066(6)	0.7121(2)	0.04405(8)	0.0307(3)
C17	0.02682(6)	0.1130(2)	0.87624(9)	0.0327(3)

Table 4. Bond lengths (Å) for marc.

O1-C13	1.2024(17)	O2-C13	1.3384(16)
O2-C14	1.4571(18)	O3-C3	1.2237(17)
O4-C4	1.3553(16)	O4-H4A	0.84
C1-C5	1.5235(18)	C1-C11	1.5381(18)
C1-C12	1.5419(19)	C1-C2	1.5987(18)
C2-C3	1.5255(17)	C2-C16	1.5301(18)
C2-C13	1.5328(19)	C3-C4	1.4500(18)
C4-C5	1.3427(18)	C5-C17	1.4995(19)
C6-C7	1.390(2)	C6-C11	1.393(2)
C6-H6A	0.95	C7-C8	1.381(3)
C7-H7A	0.95	C8-C9	1.382(3)
C8-H8A	0.95	C9-C10	1.391(2)
C9-H9A	0.95	C10-C11	1.394(2)
C10-H10	0.95	C12-H12A	0.98
C12-H12B	0.98	C12-H12C	0.98
C14-C15	1.497(2)	C14-H14A	0.99
C14-H14B	0.99	C15-H15A	0.98
C15-H15B	0.98	C15-H15C	0.98
C16-H16A	0.98	C16-H16B	0.98
C16-H16C	0.98	C17-H17A	0.98
C17-H17B	0.98	C17-H17C	0.98

Table 5. Bond angles (°) for marc.

C13-O2-C14	116.24(11)	C4-O4-H4A	109.5
C5-C1-C11	112.46(11)	C5-C1-C12	107.26(11)
C11-C1-C12	110.16(11)	C5-C1-C2	102.89(10)
C11-C1-C2	111.82(10)	C12-C1-C2	111.99(11)
C3-C2-C16	109.39(11)	C3-C2-C13	107.97(10)
C16-C2-C13	108.43(11)	C3-C2-C1	103.62(10)
C16-C2-C1	116.11(11)	C13-C2-C1	110.98(10)
O3-C3-C4	126.74(12)	O3-C3-C2	124.30(12)
C4-C3-C2	108.93(11)	C5-C4-O4	125.65(12)
C5-C4-C3	111.33(11)	O4-C4-C3	122.99(12)
C4-C5-C17	124.11(12)	C4-C5-C1	112.57(11)
C17-C5-C1	123.02(12)	C7-C6-C11	121.30(15)
C7-C6-H6A	119.3	C11-C6-H6A	119.3
C8-C7-C6	120.10(16)	C8-C7-H7A	119.9
C6-C7-H7A	119.9	C7-C8-C9	119.36(15)
C7-C8-H8A	120.3	C9-C8-H8A	120.3
C8-C9-C10	120.65(16)	C8-C9-H9A	119.7
C10-C9-H9A	119.7	C9-C10-C11	120.70(15)
C9-C10-H10	119.7	C11-C10-H10	119.7
C6-C11-C10	117.89(13)	C6-C11-C1	121.57(12)
C10-C11-C1	120.50(12)	C1-C12-H12A	109.5
C1-C12-H12B	109.5	H12A-C12-H12B	109.5
C1-C12-H12C	109.5	H12A-C12-H12C	109.5
H12B-C12-H12C	109.5	O1-C13-O2	124.19(13)
O1-C13-C2	124.46(13)	O2-C13-C2	111.35(11)
O2-C14-C15	107.61(14)	O2-C14-H14A	110.2
C15-C14-H14A	110.2	O2-C14-H14B	110.2
C15-C14-H14B	110.2	H14A-C14-H14B	108.5
C14-C15-H15A	109.5	C14-C15-H15B	109.5
H15A-C15-H15B	109.5	C14-C15-H15C	109.5
H15A-C15-H15C	109.5	H15B-C15-H15C	109.5
C2-C16-H16A	109.5	C2-C16-H16B	109.5
H16A-C16-H16B	109.5	C2-C16-H16C	109.5
H16A-C16-H16C	109.5	H16B-C16-H16C	109.5
C5-C17-H17A	109.5	C5-C17-H17B	109.5
H17A-C17-H17B	109.5	C5-C17-H17C	109.5
H17A-C17-H17C	109.5	H17B-C17-H17C	109.5

Table 6. Torsion angles (°) for marc.

C5-C1-C2-C3	-7.79(12)	C11-C1-C2-C3	-128.72(11)
C12-C1-C2-C3	107.09(12)	C5-C1-C2-C16	-127.74(12)
C11-C1-C2-C16	111.33(13)	C12-C1-C2-C16	-12.86(15)
C5-C1-C2-C13	107.86(11)	C11-C1-C2-C13	-13.06(14)
C12-C1-C2-C13	-137.26(11)	C16-C2-C3-O3	-46.57(18)
C13-C2-C3-O3	71.24(16)	C1-C2-C3-O3	-171.00(13)
C16-C2-C3-C4	131.43(12)	C13-C2-C3-C4	-110.77(12)
C1-C2-C3-C4	7.00(13)	O3-C3-C4-C5	174.64(13)
C2-C3-C4-C5	-3.29(15)	O3-C3-C4-O4	-3.5(2)
C2-C3-C4-O4	178.59(11)	O4-C4-C5-C17	1.9(2)
C3-C4-C5-C17	-176.16(13)	O4-C4-C5-C1	175.74(12)
C3-C4-C5-C1	-2.32(16)	C11-C1-C5-C4	127.01(12)
C12-C1-C5-C4	-111.72(13)	C2-C1-C5-C4	6.53(14)
C11-C1-C5-C17	-59.06(16)	C12-C1-C5-C17	62.20(16)
C2-C1-C5-C17	-179.55(12)	C11-C6-C7-C8	-0.3(2)
C6-C7-C8-C9	0.3(3)	C7-C8-C9-C10	-0.3(3)
C8-C9-C10-C11	0.4(3)	C7-C6-C11-C10	0.4(2)
C7-C6-C11-C1	-176.99(13)	C9-C10-C11-C6	-0.5(2)
C9-C10-C11-C1	176.97(14)	C5-C1-C11-C6	-23.64(17)
C12-C1-C11-C6	-143.24(13)	C2-C1-C11-C6	91.55(14)
C5-C1-C11-C10	159.01(12)	C12-C1-C11-C10	39.42(17)
C2-C1-C11-C10	-85.79(15)	C14-O2-C13-O1	-8.78(19)
C14-O2-C13-C2	170.95(11)	C3-C2-C13-O1	-142.83(13)
C16-C2-C13-O1	-24.41(17)	C1-C2-C13-O1	104.24(15)
C3-C2-C13-O2	37.44(14)	C16-C2-C13-O2	155.86(11)
C1-C2-C13-O2	-75.49(13)	C13-O2-C14-C15	-171.29(12)

Table 7. Anisotropic atomic displacement parameters (Å²) for marc.

The anisotropic atomic displacement factor exponent takes the form: -2π²[ h² a^*2 U₁₁ + ... + 2 h k a^* b^* U₁₂ ]

	U₁₁	U₂₂	U₃₃	U₂₃	U₁₃	U₁₂
O1	0.0223(5)	0.0386(6)	0.0512(7)	-0.0047(5)	0.0092(5)	0.0058(4)
O2	0.0255(5)	0.0277(5)	0.0247(5)	-0.0034(4)	0.0077(4)	0.0004(4)
O3	0.0265(5)	0.0290(5)	0.0449(7)	0.0127(5)	0.0144(5)	-0.0013(4)
O4	0.0175(5)	0.0340(5)	0.0378(6)	0.0096(4)	0.0068(4)	-0.0006(4)
C1	0.0215(6)	0.0204(6)	0.0195(6)	0.0011(5)	0.0057(5)	-0.0013(5)
C2	0.0172(6)	0.0225(6)	0.0200(6)	0.0032(5)	0.0046(5)	-0.0011(5)
C3	0.0205(6)	0.0237(6)	0.0203(6)	-0.0004(5)	0.0071(5)	-0.0021(5)
C4	0.0176(6)	0.0266(6)	0.0203(6)	0.0001(5)	0.0057(5)	0.0006(5)
C5	0.0221(6)	0.0249(6)	0.0197(6)	0.0001(5)	0.0071(5)	0.0022(5)
C6	0.0351(8)	0.0275(7)	0.0263(7)	0.0028(5)	0.0101(6)	0.0003(6)
C7	0.0539(10)	0.0410(9)	0.0253(8)	0.0069(7)	0.0146(7)	0.0085(7)
C8	0.0497(10)	0.0532(10)	0.0390(9)	0.0206(8)	0.0294(8)	0.0173(8)
C9	0.0297(8)	0.0572(11)	0.0466(10)	0.0216(8)	0.0196(7)	0.0088(7)
C10	0.0247(7)	0.0381(8)	0.0342(8)	0.0120(6)	0.0103(6)	0.0038(6)
C11	0.0255(7)	0.0199(6)	0.0247(7)	0.0049(5)	0.0107(5)	0.0029(5)
C12	0.0343(8)	0.0283(7)	0.0299(8)	-0.0070(6)	0.0090(6)	-0.0059(6)
C13	0.0209(6)	0.0190(6)	0.0278(7)	0.0046(5)	0.0072(5)	-0.0017(5)
C14	0.0466(9)	0.0310(8)	0.0318(8)	-0.0057(6)	0.0177(7)	0.0035(6)
C15	0.0644(12)	0.0441(10)	0.0295(9)	-0.0077(7)	0.0089(8)	-0.0029(8)
C16	0.0268(7)	0.0378(8)	0.0249(7)	0.0060(6)	-0.0016(6)	-0.0029(6)
C17	0.0326(8)	0.0290(7)	0.0377(8)	0.0078(6)	0.0095(6)	0.0072(6)

Table 8. Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å²) for marc.

	x/a	y/b	z/c	U(eq)
H4A	-0.0283	0.6768	0.9530	0.044
H6A	0.0814	0.8987	0.7776	0.035
H7A	0.1245	0.9346	0.6721	0.047
H8A	0.2177	1.0272	0.6908	0.053
H9A	0.2675	1.0804	0.8158	0.051
H10	0.2247	1.0453	0.9217	0.038
H12A	0.1345	1.2049	0.9708	0.046
H12B	0.1810	1.0655	1.0146	0.046
H12C	0.1202	1.0685	1.0355	0.046
H14A	0.1476	0.3383	0.8008	0.042
H14B	0.1631	0.5339	0.7676	0.042
H15A	0.0542	0.3757	0.7367	0.069
H15B	0.0945	0.3844	0.6756	0.069
H15C	0.0695	0.5708	0.7037	0.069
H16A	0.1553	0.7843	1.0819	0.046
H16B	0.2078	0.7589	1.0413	0.046
H16C	0.1734	0.5821	1.0598	0.046
H17A	-0.0129	1.0837	0.8600	0.049
H17B	0.0417	1.1533	0.8313	0.049
H17C	0.0315	1.2121	0.9148	0.049

Table 9. Hydrogen bond distances (Å) and angles (°) for marc.

	Donor-H	Acceptor-H	Donor-Acceptor	Angle
O4-H4A^...O3	0.84	1.92	2.7340(15)	162.4