Tetra-methyl 4,4'-carbonyl-bis(benzene-1,2-dicarboxyl-ate).

In the mol-ecule of the title compound, C(21)H(18)O(9), the two aromatic rings are aligned at an angle of 49.7 (1)°.

Related literature

For the parent acid monohydrate, see: Fitzgerald & Gerkin (1997 ▶). For related literature, see: Zhang et al. (2004 ▶).

Experimental

Crystal data

C21H18O9

M = 414.35

Monoclinic,

a = 11.8627 (2) Å

b = 17.3678 (3) Å

c = 9.2506 (2) Å

β = 95.150 (1)°

V = 1898.20 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 123 K

0.45 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

14279 measured reflections

4339 independent reflections

3596 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.139

S = 1.04

4339 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.89 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009271/tk2392sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009271/tk2392Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H18O9	F(000) = 864
Mr = 414.35	Dx = 1.450 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5155 reflections
a = 11.8627 (2) Å	θ = 2.9–28.2°
b = 17.3678 (3) Å	µ = 0.12 mm−1
c = 9.2506 (2) Å	T = 123 K
β = 95.150 (1)°	Block, colorless
V = 1898.20 (6) Å3	0.45 × 0.15 × 0.05 mm
Z = 4

Bruker SMART APEX [APEXII?] diffractometer	3596 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 27.5°, θmin = 1.7°
ω scans	h = −15→15
14279 measured reflections	k = −22→22
4339 independent reflections	l = −11→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0704P)2 + 1.4144P] where P = (Fo2 + 2Fc2)/3
4339 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.89 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.82828 (10)	0.56029 (7)	0.93784 (12)	0.0205 (3)
O2	1.01037 (11)	0.56968 (8)	0.88890 (13)	0.0261 (3)
O3	0.89532 (11)	0.62457 (7)	0.42114 (13)	0.0227 (3)
O4	0.87735 (13)	0.65645 (7)	0.65258 (14)	0.0288 (3)
O5	0.47658 (11)	0.33391 (8)	0.30590 (16)	0.0310 (3)
O6	0.38426 (16)	0.22311 (10)	0.2777 (3)	0.0726 (7)
O7	0.50941 (16)	0.09165 (11)	0.19849 (17)	0.0525 (5)
O8	0.42373 (14)	0.05561 (10)	0.38926 (19)	0.0458 (4)
O9	0.85745 (11)	0.25995 (7)	0.79479 (13)	0.0236 (3)
C1	0.82935 (13)	0.36953 (9)	0.64550 (17)	0.0163 (3)
C2	0.85873 (13)	0.42065 (9)	0.75874 (17)	0.0165 (3)
H2	0.8650	0.4026	0.8561	0.020*
C3	0.87895 (13)	0.49763 (9)	0.73051 (17)	0.0160 (3)
C4	0.87127 (13)	0.52414 (9)	0.58682 (17)	0.0158 (3)
C5	0.84754 (14)	0.47205 (9)	0.47349 (17)	0.0180 (3)
H5	0.8463	0.4892	0.3759	0.022*
C6	0.82574 (14)	0.39516 (9)	0.50221 (17)	0.0177 (3)
H6	0.8084	0.3602	0.4245	0.021*
C7	0.91496 (14)	0.54819 (9)	0.85827 (17)	0.0173 (3)
C8	0.85333 (17)	0.60385 (11)	1.07015 (19)	0.0262 (4)
H8A	0.7826	0.6222	1.1053	0.039*
H8B	0.9012	0.6480	1.0508	0.039*
H8C	0.8932	0.5709	1.1440	0.039*
C9	0.88242 (14)	0.60863 (9)	0.55979 (17)	0.0170 (3)
C10	0.90221 (18)	0.70612 (10)	0.3881 (2)	0.0280 (4)
H10A	0.8282	0.7302	0.3952	0.042*
H10B	0.9246	0.7126	0.2894	0.042*
H10C	0.9585	0.7306	0.4573	0.042*
C11	0.72742 (14)	0.23959 (9)	0.59007 (17)	0.0168 (3)
C12	0.63715 (14)	0.27188 (9)	0.50347 (18)	0.0187 (3)
H12	0.6268	0.3261	0.5024	0.022*
C13	0.56220 (14)	0.22528 (10)	0.41868 (19)	0.0210 (4)
C14	0.57621 (15)	0.14533 (10)	0.42228 (19)	0.0220 (4)
C15	0.66549 (15)	0.11274 (10)	0.50977 (19)	0.0223 (4)
H15	0.6748	0.0584	0.5127	0.027*
C16	0.74083 (14)	0.15960 (9)	0.59265 (18)	0.0189 (3)
H16	0.8019	0.1372	0.6515	0.023*
C17	0.46489 (16)	0.25921 (11)	0.3262 (2)	0.0287 (4)
C18	0.38474 (18)	0.37057 (13)	0.2166 (2)	0.0354 (5)
H18A	0.3787	0.3477	0.1194	0.053*
H18B	0.4001	0.4258	0.2094	0.053*
H18C	0.3136	0.3629	0.2609	0.053*
C19	0.49327 (17)	0.09303 (11)	0.3372 (2)	0.0300 (4)
C20	0.4158 (3)	0.0543 (2)	0.1117 (3)	0.0687 (9)
H20A	0.4090	0.0008	0.1436	0.103*
H20B	0.4303	0.0552	0.0091	0.103*
H20C	0.3452	0.0819	0.1242	0.103*
C21	0.80855 (14)	0.28732 (9)	0.68492 (17)	0.0172 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0222 (6)	0.0240 (6)	0.0151 (5)	0.0013 (5)	−0.0003 (4)	−0.0048 (5)
O2	0.0248 (7)	0.0309 (7)	0.0223 (6)	−0.0094 (5)	0.0005 (5)	−0.0043 (5)
O3	0.0370 (7)	0.0143 (6)	0.0168 (6)	−0.0020 (5)	0.0027 (5)	0.0017 (4)
O4	0.0485 (9)	0.0173 (6)	0.0217 (6)	−0.0032 (6)	0.0094 (6)	−0.0037 (5)
O5	0.0251 (7)	0.0254 (7)	0.0403 (8)	0.0007 (5)	−0.0099 (6)	0.0103 (6)
O6	0.0480 (11)	0.0316 (9)	0.1273 (19)	−0.0056 (8)	−0.0526 (12)	0.0061 (10)
O7	0.0661 (12)	0.0602 (11)	0.0298 (8)	−0.0355 (9)	−0.0036 (8)	−0.0023 (7)
O8	0.0378 (9)	0.0433 (9)	0.0561 (10)	−0.0220 (7)	0.0039 (7)	−0.0106 (8)
O9	0.0298 (7)	0.0194 (6)	0.0205 (6)	−0.0013 (5)	−0.0032 (5)	0.0045 (5)
C1	0.0158 (7)	0.0157 (7)	0.0171 (7)	0.0003 (6)	0.0003 (6)	0.0000 (6)
C2	0.0172 (8)	0.0178 (8)	0.0141 (7)	−0.0019 (6)	−0.0004 (6)	0.0013 (6)
C3	0.0149 (7)	0.0177 (8)	0.0154 (7)	−0.0014 (6)	0.0007 (6)	−0.0014 (6)
C4	0.0158 (7)	0.0157 (7)	0.0160 (7)	−0.0004 (6)	0.0010 (6)	0.0004 (6)
C5	0.0222 (8)	0.0180 (8)	0.0137 (7)	−0.0007 (6)	0.0016 (6)	0.0014 (6)
C6	0.0215 (8)	0.0164 (8)	0.0150 (7)	−0.0006 (6)	0.0001 (6)	−0.0030 (6)
C7	0.0215 (8)	0.0159 (7)	0.0140 (7)	−0.0020 (6)	−0.0006 (6)	0.0018 (6)
C8	0.0336 (10)	0.0275 (9)	0.0173 (8)	0.0032 (7)	−0.0001 (7)	−0.0071 (7)
C9	0.0172 (8)	0.0167 (7)	0.0169 (7)	−0.0003 (6)	0.0007 (6)	0.0001 (6)
C10	0.0433 (11)	0.0146 (8)	0.0260 (9)	−0.0018 (7)	0.0029 (8)	0.0046 (7)
C11	0.0185 (8)	0.0154 (7)	0.0168 (8)	−0.0009 (6)	0.0033 (6)	−0.0005 (6)
C12	0.0186 (8)	0.0145 (7)	0.0231 (8)	0.0004 (6)	0.0032 (6)	0.0013 (6)
C13	0.0186 (8)	0.0186 (8)	0.0257 (9)	−0.0006 (6)	0.0018 (7)	0.0018 (6)
C14	0.0203 (8)	0.0187 (8)	0.0270 (9)	−0.0035 (6)	0.0013 (7)	−0.0009 (7)
C15	0.0260 (9)	0.0142 (8)	0.0266 (9)	−0.0009 (6)	0.0028 (7)	−0.0003 (6)
C16	0.0208 (8)	0.0163 (8)	0.0197 (8)	0.0010 (6)	0.0021 (6)	0.0027 (6)
C17	0.0234 (9)	0.0232 (9)	0.0377 (11)	0.0000 (7)	−0.0063 (8)	0.0000 (8)
C18	0.0290 (10)	0.0345 (11)	0.0404 (11)	0.0064 (8)	−0.0097 (9)	0.0107 (9)
C19	0.0344 (11)	0.0194 (9)	0.0345 (10)	−0.0007 (7)	−0.0072 (8)	−0.0004 (8)
C20	0.076 (2)	0.084 (2)	0.0432 (15)	−0.0364 (17)	−0.0131 (14)	−0.0089 (14)
C21	0.0191 (8)	0.0162 (8)	0.0164 (7)	0.0001 (6)	0.0031 (6)	0.0006 (6)

O1—C7	1.334 (2)	C8—H8A	0.9800
O1—C8	1.447 (2)	C8—H8B	0.9800
O2—C7	1.201 (2)	C8—H8C	0.9800
O3—C9	1.334 (2)	C10—H10A	0.9800
O3—C10	1.453 (2)	C10—H10B	0.9800
O4—C9	1.200 (2)	C10—H10C	0.9800
O5—C17	1.320 (2)	C11—C16	1.398 (2)
O5—C18	1.454 (2)	C11—C12	1.396 (2)
O6—C17	1.197 (2)	C11—C21	1.494 (2)
O7—C19	1.315 (3)	C12—C13	1.391 (2)
O7—C20	1.463 (3)	C12—H12	0.9500
O8—C19	1.186 (3)	C13—C14	1.399 (2)
O9—C21	1.220 (2)	C13—C17	1.495 (2)
C1—C2	1.393 (2)	C14—C15	1.394 (2)
C1—C6	1.395 (2)	C14—C19	1.508 (2)
C1—C21	1.500 (2)	C15—C16	1.388 (2)
C2—C3	1.387 (2)	C15—H15	0.9500
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.402 (2)	C18—H18A	0.9800
C3—C7	1.503 (2)	C18—H18B	0.9800
C4—C5	1.394 (2)	C18—H18C	0.9800
C4—C9	1.496 (2)	C20—H20A	0.9800
C5—C6	1.390 (2)	C20—H20B	0.9800
C5—H5	0.9500	C20—H20C	0.9800
C6—H6	0.9500
C7—O1—C8	116.05 (14)	C16—C11—C12	119.28 (15)
C9—O3—C10	114.72 (13)	C16—C11—C21	118.36 (15)
C17—O5—C18	115.37 (15)	C12—C11—C21	122.33 (14)
C19—O7—C20	111.96 (19)	C13—C12—C11	120.56 (15)
C2—C1—C6	119.69 (15)	C13—C12—H12	119.7
C2—C1—C21	117.35 (14)	C11—C12—H12	119.7
C6—C1—C21	122.89 (14)	C12—C13—C14	119.71 (16)
C3—C2—C1	120.55 (14)	C12—C13—C17	121.00 (15)
C3—C2—H2	119.7	C14—C13—C17	119.28 (16)
C1—C2—H2	119.7	C15—C14—C13	119.97 (16)
C2—C3—C4	119.83 (14)	C15—C14—C19	118.98 (15)
C2—C3—C7	117.18 (14)	C13—C14—C19	121.01 (16)
C4—C3—C7	122.91 (14)	C16—C15—C14	120.04 (15)
C5—C4—C3	119.43 (14)	C16—C15—H15	120.0
C5—C4—C9	121.71 (14)	C14—C15—H15	120.0
C3—C4—C9	118.77 (14)	C15—C16—C11	120.44 (15)
C6—C5—C4	120.53 (14)	C15—C16—H16	119.8
C6—C5—H5	119.7	C11—C16—H16	119.8
C4—C5—H5	119.7	O6—C17—O5	123.51 (18)
C5—C6—C1	119.84 (14)	O6—C17—C13	123.94 (18)
C5—C6—H6	120.1	O5—C17—C13	112.54 (15)
C1—C6—H6	120.1	O5—C18—H18A	109.5
O2—C7—O1	125.28 (15)	O5—C18—H18B	109.5
O2—C7—C3	124.21 (15)	H18A—C18—H18B	109.5
O1—C7—C3	110.31 (13)	O5—C18—H18C	109.5
O1—C8—H8A	109.5	H18A—C18—H18C	109.5
O1—C8—H8B	109.5	H18B—C18—H18C	109.5
H8A—C8—H8B	109.5	O8—C19—O7	123.63 (19)
O1—C8—H8C	109.5	O8—C19—C14	124.31 (19)
H8A—C8—H8C	109.5	O7—C19—C14	112.02 (17)
H8B—C8—H8C	109.5	O7—C20—H20A	109.5
O4—C9—O3	124.16 (15)	O7—C20—H20B	109.5
O4—C9—C4	123.26 (15)	H20A—C20—H20B	109.5
O3—C9—C4	112.55 (13)	O7—C20—H20C	109.5
O3—C10—H10A	109.5	H20A—C20—H20C	109.5
O3—C10—H10B	109.5	H20B—C20—H20C	109.5
H10A—C10—H10B	109.5	O9—C21—C11	120.40 (14)
O3—C10—H10C	109.5	O9—C21—C1	119.80 (15)
H10A—C10—H10C	109.5	C11—C21—C1	119.80 (13)
H10B—C10—H10C	109.5
C6—C1—C2—C3	3.2 (2)	C12—C13—C14—C15	−0.5 (3)
C21—C1—C2—C3	−179.84 (14)	C17—C13—C14—C15	−178.97 (17)
C1—C2—C3—C4	−0.8 (2)	C12—C13—C14—C19	177.06 (17)
C1—C2—C3—C7	−177.49 (15)	C17—C13—C14—C19	−1.4 (3)
C2—C3—C4—C5	−2.4 (2)	C13—C14—C15—C16	−0.4 (3)
C7—C3—C4—C5	174.02 (15)	C19—C14—C15—C16	−177.95 (17)
C2—C3—C4—C9	174.17 (14)	C14—C15—C16—C11	0.5 (3)
C7—C3—C4—C9	−9.4 (2)	C12—C11—C16—C15	0.2 (2)
C3—C4—C5—C6	3.4 (2)	C21—C11—C16—C15	178.04 (15)
C9—C4—C5—C6	−173.13 (15)	C18—O5—C17—O6	−1.2 (3)
C4—C5—C6—C1	−1.0 (2)	C18—O5—C17—C13	179.94 (17)
C2—C1—C6—C5	−2.3 (2)	C12—C13—C17—O6	−162.3 (2)
C21—C1—C6—C5	−179.05 (15)	C14—C13—C17—O6	16.2 (3)
C8—O1—C7—O2	0.9 (2)	C12—C13—C17—O5	16.6 (3)
C8—O1—C7—C3	175.88 (13)	C14—C13—C17—O5	−164.95 (17)
C2—C3—C7—O2	103.63 (19)	C20—O7—C19—O8	14.0 (3)
C4—C3—C7—O2	−72.9 (2)	C20—O7—C19—C14	−168.1 (2)
C2—C3—C7—O1	−71.44 (18)	C15—C14—C19—O8	73.0 (3)
C4—C3—C7—O1	112.03 (17)	C13—C14—C19—O8	−104.6 (2)
C10—O3—C9—O4	−0.5 (2)	C15—C14—C19—O7	−104.9 (2)
C10—O3—C9—C4	177.76 (14)	C13—C14—C19—O7	77.6 (2)
C5—C4—C9—O4	162.70 (17)	C16—C11—C21—O9	−25.3 (2)
C3—C4—C9—O4	−13.8 (2)	C12—C11—C21—O9	152.50 (16)
C5—C4—C9—O3	−15.5 (2)	C16—C11—C21—C1	155.19 (15)
C3—C4—C9—O3	167.94 (14)	C12—C11—C21—C1	−27.0 (2)
C16—C11—C12—C13	−1.0 (2)	C2—C1—C21—O9	−29.0 (2)
C21—C11—C12—C13	−178.79 (15)	C6—C1—C21—O9	147.90 (17)
C11—C12—C13—C14	1.2 (3)	C2—C1—C21—C11	150.56 (15)
C11—C12—C13—C17	179.64 (16)	C6—C1—C21—C11	−32.6 (2)