marc002

Crystal Structure Report for marc002

A specimen of C₂₀H₁₇BrO₄, approximate dimensions 0.086 mm x 0.371 mm x 0.453 mm, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured.

The total exposure time was 1.36 hours. The frames were integrated with the Bruker SAINT software package using a wide-frame algorithm. The integration of the data using a monoclinic unit cell yielded a total of 19560 reflections to a maximum θ angle of 74.78° (0.80 Å resolution), of which 3698 were independent (average redundancy 5.289, completeness = 99.6%, R_int = 6.85%, R_sig = 4.90%) and 3523 (95.27%) were greater than 2σ(F²). The final cell constants of a = 6.8349(3) Å, b = 7.3672(3) Å, c = 18.3255(8) Å, β = 100.593(2)°, volume = 907.04(7) Å³, are based upon the refinement of the XYZ-centroids of 6433 reflections above 20 σ(I) with 4.905° < 2θ < 147.8°. Data were corrected for absorption effects using the multi-scan method (SADABS). The ratio of minimum to maximum apparent transmission was 0.612. The calculated minimum and maximum transmission coefficients (based on crystal size) are 0.4614 and 0.7538.

The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group P 1 21 1, with Z = 2 for the formula unit, C₂₀H₁₇BrO₄. The final anisotropic full-matrix least-squares refinement on F² with 232 variables converged at R1 = 4.41%, for the observed data and wR2 = 12.14% for all data. The goodness-of-fit was 1.114. The largest peak in the final difference electron density synthesis was 0.634 e^-/Å³ and the largest hole was -0.412 e^-/Å³ with an RMS deviation of 0.060 e^-/Å³. On the basis of the final model, the calculated density was 1.469 g/cm³ and F(000), 408 e^-.

Table 1. Sample and crystal data for marc002.

Identification code	marc002
Chemical formula	C₂₀H₁₇BrO₄
Formula weight	401.24
Temperature	200(2) K
Wavelength	1.54178 Å
Crystal size	0.086 x 0.371 x 0.453 mm
Crystal system	monoclinic
Space group	P 1 21 1
Unit cell dimensions	a = 6.8349(3) Å	α = 90°
	b = 7.3672(3) Å	β = 100.593(2)°
	c = 18.3255(8) Å	γ = 90°
Volume	907.04(7) Å³
Z	2
Density (calculated)	1.469 g/cm³
Absorption coefficient	3.269 mm^-1
F(000)	408

Table 2. Data collection and structure refinement for marc002.

Theta range for data collection	2.45 to 74.78°
Index ranges	-8<=h<=8, -9<=k<=9, -22<=l<=22
Reflections collected	19560
Independent reflections	3698 [R(int) = 0.0685]
Coverage of independent reflections	99.6%
Absorption correction	multi-scan
Max. and min. transmission	0.7538 and 0.4614
Structure solution technique	direct methods
Structure solution program	SHELXS-97 (Sheldrick 2008)
Refinement method	Full-matrix least-squares on F²
Refinement program	SHELXL-2014/7 (Sheldrick, 2014)
Function minimized	Σ w(F_o² - F_c²)²
Data / restraints / parameters	3698 / 1 / 232
Goodness-of-fit on F²	1.114
Final R indices	3523 data; I>2σ(I)	R1 = 0.0441, wR2 = 0.1201
	all data	R1 = 0.0455, wR2 = 0.1214
Weighting scheme	w=1/[σ²(F_o²)+(0.0749P)²+0.0991P] where P=(F_o²+2F_c²)/3
Absolute structure parameter	-0.0(0)
Extinction coefficient	0.0098(15)
Largest diff. peak and hole	0.634 and -0.412 eÅ^-3
R.M.S. deviation from mean	0.060 eÅ^-3

Table 3. Atomic coordinates and equivalent isotropic atomic displacement parameters (Å²) for marc002.

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

	x/a	y/b	z/c	U(eq)
C1	0.6532(6)	0.4414(6)	0.3727(2)	0.0272(8)
C2	0.6327(6)	0.5490(7)	0.4422(3)	0.0307(9)
C3	0.7719(6)	0.7007(7)	0.4489(3)	0.0323(9)
C4	0.8755(6)	0.7012(6)	0.3940(3)	0.0297(9)
C5	0.8057(6)	0.5548(6)	0.3372(2)	0.0267(8)
C6	0.4501(6)	0.4208(5)	0.3231(2)	0.0275(9)
C7	0.2662(8)	0.3247(8)	0.1448(3)	0.0439(12)
C8	0.0970(10)	0.2723(11)	0.0937(4)	0.0590(16)
C9	0.9528(10)	0.1670(9)	0.1173(4)	0.0603(17)
C10	0.9738(9)	0.1152(8)	0.1898(4)	0.0529(14)
C11	0.1402(8)	0.1658(7)	0.2409(3)	0.0427(11)
C12	0.2838(6)	0.2695(6)	0.2160(3)	0.0325(9)
C13	0.7362(7)	0.2524(7)	0.3963(3)	0.0363(10)
C14	0.0427(7)	0.8248(7)	0.3861(3)	0.0396(11)
C15	0.8098(7)	0.5961(7)	0.2007(3)	0.0323(9)
C16	0.7352(7)	0.6672(7)	0.1312(3)	0.0366(10)
C17	0.5735(8)	0.7821(7)	0.1230(3)	0.0373(10)
C18	0.4866(8)	0.8301(7)	0.1825(3)	0.0386(11)
C19	0.5658(7)	0.7619(7)	0.2520(3)	0.0350(10)
C20	0.7246(6)	0.6391(6)	0.2618(3)	0.0287(9)
O1	0.2980(5)	0.4896(6)	0.3333(2)	0.0438(9)
O2	0.4621(4)	0.3107(5)	0.26562(18)	0.0336(7)
O3	0.5286(5)	0.5081(6)	0.4871(2)	0.0436(9)
O4	0.8048(5)	0.8140(6)	0.5088(2)	0.0435(9)
Br1	0.46638(10)	0.88088(9)	0.02817(3)	0.0548(3)

Table 4. Bond lengths (Å) for marc002.

C1-C6	1.520(6)	C1-C2	1.527(6)
C1-C13	1.536(6)	C1-C5	1.568(5)
C2-O3	1.222(5)	C2-C3	1.458(7)
C3-C4	1.332(6)	C3-O4	1.365(6)
C4-C14	1.489(6)	C4-C5	1.514(6)
C5-C20	1.523(6)	C5-H5	1.0
C6-O1	1.202(5)	C6-O2	1.344(5)
C7-C12	1.351(7)	C7-C8	1.402(8)
C7-H7	0.95	C8-C9	1.385(11)
C8-H8	0.95	C9-C10	1.364(10)
C9-H9	0.95	C10-C11	1.385(8)
C10-H10	0.95	C11-C12	1.386(7)
C11-H11	0.95	C12-O2	1.413(5)
C13-H13A	0.98	C13-H13B	0.98
C13-H13C	0.98	C14-H14A	0.98
C14-H14B	0.98	C14-H14C	0.98
C15-C16	1.385(7)	C15-C20	1.391(6)
C15-H15	0.95	C16-C17	1.378(7)
C16-H16	0.95	C17-C18	1.381(7)
C17-Br1	1.902(5)	C18-C19	1.382(7)
C18-H18	0.95	C19-C20	1.399(6)
C19-H19	0.95	O4-H4	0.77(8)

Table 5. Bond angles (°) for marc002.

C6-C1-C2	109.7(3)	C6-C1-C13	109.1(4)
C2-C1-C13	108.8(4)	C6-C1-C5	114.1(4)
C2-C1-C5	103.9(3)	C13-C1-C5	111.1(3)
O3-C2-C3	125.7(5)	O3-C2-C1	126.0(5)
C3-C2-C1	108.0(3)	C4-C3-O4	125.1(4)
C4-C3-C2	111.6(4)	O4-C3-C2	123.0(4)
C3-C4-C14	126.8(4)	C3-C4-C5	111.9(4)
C14-C4-C5	121.3(4)	C4-C5-C20	110.5(4)
C4-C5-C1	104.1(3)	C20-C5-C1	115.8(3)
C4-C5-H5	108.8	C20-C5-H5	108.8
C1-C5-H5	108.8	O1-C6-O2	123.8(4)
O1-C6-C1	125.8(4)	O2-C6-C1	110.4(3)
C12-C7-C8	118.6(5)	C12-C7-H7	120.7
C8-C7-H7	120.7	C9-C8-C7	119.5(6)
C9-C8-H8	120.3	C7-C8-H8	120.3
C10-C9-C8	120.5(6)	C10-C9-H9	119.7
C8-C9-H9	119.7	C9-C10-C11	120.7(6)
C9-C10-H10	119.7	C11-C10-H10	119.7
C10-C11-C12	117.9(6)	C10-C11-H11	121.0
C12-C11-H11	121.0	C7-C12-C11	122.8(5)
C7-C12-O2	118.0(4)	C11-C12-O2	119.0(5)
C1-C13-H13A	109.5	C1-C13-H13B	109.5
H13A-C13-H13B	109.5	C1-C13-H13C	109.5
H13A-C13-H13C	109.5	H13B-C13-H13C	109.5
C4-C14-H14A	109.5	C4-C14-H14B	109.5
H14A-C14-H14B	109.5	C4-C14-H14C	109.5
H14A-C14-H14C	109.5	H14B-C14-H14C	109.5
C16-C15-C20	121.1(4)	C16-C15-H15	119.5
C20-C15-H15	119.5	C17-C16-C15	119.0(4)
C17-C16-H16	120.5	C15-C16-H16	120.5
C16-C17-C18	121.6(5)	C16-C17-Br1	120.0(4)
C18-C17-Br1	118.3(4)	C17-C18-C19	118.8(5)
C17-C18-H18	120.6	C19-C18-H18	120.6
C18-C19-C20	121.1(4)	C18-C19-H19	119.4
C20-C19-H19	119.4	C15-C20-C19	118.3(4)
C15-C20-C5	120.1(4)	C19-C20-C5	121.7(4)
C6-O2-C12	117.7(3)	C3-O4-H4	111.(6)

Table 6. Torsion angles (°) for marc002.

C6-C1-C2-O3	58.3(6)	C13-C1-C2-O3	-60.9(6)
C5-C1-C2-O3	-179.4(5)	C6-C1-C2-C3	-126.5(4)
C13-C1-C2-C3	114.3(4)	C5-C1-C2-C3	-4.2(5)
O3-C2-C3-C4	174.9(5)	C1-C2-C3-C4	-0.3(5)
O3-C2-C3-O4	1.6(8)	C1-C2-C3-O4	-173.7(4)
O4-C3-C4-C14	-1.1(8)	C2-C3-C4-C14	-174.2(4)
O4-C3-C4-C5	178.2(4)	C2-C3-C4-C5	5.1(6)
C3-C4-C5-C20	117.4(4)	C14-C4-C5-C20	-63.2(5)
C3-C4-C5-C1	-7.5(5)	C14-C4-C5-C1	171.9(4)
C6-C1-C5-C4	126.0(4)	C2-C1-C5-C4	6.7(4)
C13-C1-C5-C4	-110.1(4)	C6-C1-C5-C20	4.6(5)
C2-C1-C5-C20	-114.8(4)	C13-C1-C5-C20	128.4(4)
C2-C1-C6-O1	5.3(6)	C13-C1-C6-O1	124.4(5)
C5-C1-C6-O1	-110.7(5)	C2-C1-C6-O2	-173.6(4)
C13-C1-C6-O2	-54.6(4)	C5-C1-C6-O2	70.4(4)
C12-C7-C8-C9	0.3(9)	C7-C8-C9-C10	0.5(10)
C8-C9-C10-C11	-0.5(10)	C9-C10-C11-C12	-0.2(9)
C8-C7-C12-C11	-1.1(8)	C8-C7-C12-O2	175.0(5)
C10-C11-C12-C7	1.0(8)	C10-C11-C12-O2	-175.0(5)
C20-C15-C16-C17	-0.1(7)	C15-C16-C17-C18	1.1(7)
C15-C16-C17-Br1	-179.6(4)	C16-C17-C18-C19	0.6(8)
Br1-C17-C18-C19	-178.8(4)	C17-C18-C19-C20	-3.2(8)
C16-C15-C20-C19	-2.4(7)	C16-C15-C20-C5	178.2(4)
C18-C19-C20-C15	4.1(7)	C18-C19-C20-C5	-176.6(4)
C4-C5-C20-C15	120.8(4)	C1-C5-C20-C15	-121.3(4)
C4-C5-C20-C19	-58.5(5)	C1-C5-C20-C19	59.4(5)
O1-C6-O2-C12	-2.1(7)	C1-C6-O2-C12	176.8(4)
C7-C12-O2-C6	116.6(5)	C11-C12-O2-C6	-67.2(6)

Table 7. Anisotropic atomic displacement parameters (Å²) for marc002.

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
C1	0.0213(17)	0.031(2)	0.030(2)	-0.0021(16)	0.0067(15)	0.0027(15)
C2	0.0207(17)	0.042(2)	0.030(2)	-0.0035(18)	0.0040(15)	0.0014(17)
C3	0.0229(17)	0.038(2)	0.034(2)	-0.0077(18)	0.0013(15)	0.0038(17)
C4	0.0232(18)	0.032(2)	0.032(2)	-0.0029(17)	0.0017(15)	0.0035(17)
C5	0.0195(16)	0.0300(19)	0.031(2)	-0.0042(16)	0.0060(14)	-0.0009(15)
C6	0.0227(17)	0.029(2)	0.031(2)	-0.0028(15)	0.0061(15)	-0.0002(14)
C7	0.042(3)	0.052(3)	0.037(3)	-0.006(2)	0.0061(19)	-0.003(2)
C8	0.062(4)	0.070(4)	0.040(3)	-0.010(3)	-0.006(3)	-0.001(3)
C9	0.048(3)	0.055(4)	0.070(4)	-0.016(3)	-0.011(3)	-0.006(3)
C10	0.040(3)	0.044(3)	0.068(4)	-0.006(3)	-0.006(2)	-0.011(2)
C11	0.041(3)	0.036(2)	0.049(3)	0.000(2)	0.002(2)	-0.010(2)
C12	0.0262(19)	0.032(2)	0.038(2)	-0.0075(18)	0.0027(17)	-0.0001(16)
C13	0.031(2)	0.033(2)	0.044(3)	0.007(2)	0.0037(18)	0.0054(18)
C14	0.032(2)	0.040(2)	0.047(3)	-0.006(2)	0.0083(19)	-0.0082(19)
C15	0.032(2)	0.032(2)	0.034(2)	-0.0037(18)	0.0088(17)	0.0034(17)
C16	0.040(2)	0.037(2)	0.033(2)	-0.0024(19)	0.0081(18)	-0.002(2)
C17	0.044(3)	0.033(2)	0.031(2)	-0.0013(19)	-0.0025(18)	-0.0060(19)
C18	0.036(2)	0.034(2)	0.044(3)	0.0022(18)	0.0020(19)	0.0051(17)
C19	0.034(2)	0.036(2)	0.036(2)	-0.0025(18)	0.0083(18)	0.0065(18)
C20	0.0245(19)	0.029(2)	0.032(2)	-0.0004(17)	0.0040(16)	0.0011(16)
O1	0.0222(14)	0.057(2)	0.051(2)	-0.0160(18)	0.0042(13)	0.0060(15)
O2	0.0234(14)	0.0408(16)	0.0357(18)	-0.0102(14)	0.0033(12)	0.0016(13)
O3	0.0371(17)	0.063(2)	0.0340(18)	-0.0061(17)	0.0139(14)	-0.0076(16)
O4	0.0277(15)	0.060(2)	0.042(2)	-0.0231(17)	0.0033(13)	0.0012(15)
Br1	0.0748(4)	0.0464(3)	0.0362(3)	0.0056(3)	-0.0080(2)	0.0046(3)

Table 8. Hydrogen atomic coordinates and isotropic atomic displacement parameters (Å²) for marc002.

	x/a	y/b	z/c	U(eq)
H5	0.9214	0.4755	0.3325	0.032
H7	0.3664	0.3974	0.1297	0.053
H8	0.0813	0.3088	0.0432	0.071
H9	-0.1615	0.1304	0.0827	0.072
H10	-0.1267	0.0438	0.2053	0.063
H11	0.1554	0.1306	0.2915	0.051
H13A	0.6446	0.1894	0.4231	0.054
H13B	0.8665	0.2648	0.4288	0.054
H13C	0.7504	0.1822	0.3522	0.054
H14A	1.0351	0.9348	0.4156	0.059
H14B	1.0334	0.8578	0.3338	0.059
H14C	1.1696	0.7633	0.4039	0.059
H15	0.9211	0.5166	0.2067	0.039
H16	0.7945	0.6372	0.0897	0.044
H18	0.3745	0.9086	0.1759	0.046
H19	0.5114	0.7990	0.2937	0.042
H4	0.707(12)	0.853(12)	0.517(4)	0.065

Table 9. Hydrogen bond distances (Å) and angles (°) for marc002.

	Donor-H	Acceptor-H	Donor-Acceptor	Angle
O4-H4^...O3	0.77(8)	1.96(8)	2.703(5)	162.(8)