Dieth­yl cis-1,2,3,4,5,10-hexa­hydro-7,8-dimeth­yl-1,4-dioxo-2,3,4a,10a-tetra­aza­benzo[g]cyclo­pent[cd]azulene-2a,10b-dicarboxyl­ate chloro­form disolvate

The crystal structure of the title compound, 4,5-dimeth­yl-1,2-xylylene-derived diethoxy­carbon­yl glycoluril, C₂₀H₂₄N₄O₆·2CHCl₃, is reported. In the crystal structure, there are not only inter­molecular hydrogen bonds, but also π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.119
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

diethyl cis-1,2,3,4,5,10-hexahydro-7,8-dimethyl-1,4-dioxo-2,3,4a,10a- tetraazabenzo[g]cyclopent[cd]azulene-2a,10b-dicarboxylate chloroform disolvate

Crystal data

C20H24N4O6·2CHCl3	F(000) = 2688
Mr = 655.17	Dx = 1.428 Mg m^−3
Monoclinic, C2/c	Melting point: 236 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 25.216 (3) Å	Cell parameters from 3132 reflections
b = 9.9757 (9) Å	θ = 2.3–21.7°
c = 25.566 (3) Å	µ = 0.61 mm^−1
β = 108.566 (3)°	T = 293 K
V = 6096.5 (12) Å^3	Block, colourless
Z = 8	0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART Apex CCD area-detector diffractometer	5990 independent reflections
Radiation source: sealed tube	3790 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −30→31
Tmin = 0.839, Tmax = 0.868	k = −11→12
16255 measured reflections	l = −31→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.05P)^2 + 1.22P] where P = (Fo^2 + 2Fc^2)/3
5990 reflections	(Δ/σ)max < 0.001
347 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.52021 (18)	0.4523 (4)	0.41872 (16)	0.0630 (11)
H1A	0.5601	0.4586	0.4281	0.095*
H1B	0.5087	0.3615	0.4088	0.095*
H1C	0.5092	0.4788	0.4498	0.095*
C2	0.49307 (15)	0.5432 (4)	0.37079 (15)	0.0489 (9)
C3	0.46448 (13)	0.4905 (4)	0.31800 (14)	0.0418 (8)
H3	0.4636	0.3981	0.3132	0.050*
C4	0.43828 (16)	0.5688 (4)	0.27417 (15)	0.0504 (9)
C5	0.44094 (15)	0.7088 (4)	0.28036 (14)	0.0475 (8)
C6	0.46926 (14)	0.7638 (4)	0.33140 (14)	0.0462 (8)
H6	0.4710	0.8565	0.3355	0.055*
C7	0.49526 (16)	0.6824 (4)	0.37670 (16)	0.0535 (9)
C8	0.52564 (19)	0.7505 (4)	0.43250 (17)	0.0681 (12)
H8A	0.5276	0.8453	0.4271	0.102*
H8B	0.5628	0.7147	0.4472	0.102*
H8C	0.5054	0.7337	0.4579	0.102*
C9	0.40802 (13)	0.5084 (4)	0.21872 (14)	0.0418 (8)
H9A	0.4241	0.5426	0.1916	0.050*
H9B	0.4130	0.4119	0.2206	0.050*
C10	0.32681 (15)	0.6691 (3)	0.17690 (13)	0.0406 (8)
C11	0.41143 (15)	0.8002 (4)	0.23085 (14)	0.0466 (8)
H11A	0.4197	0.8928	0.2420	0.056*
H11B	0.4269	0.7823	0.2014	0.056*
C12	0.30883 (14)	0.4700 (3)	0.21533 (14)	0.0405 (7)
C13	0.26472 (15)	0.6693 (3)	0.17895 (13)	0.0414 (8)
C14	0.31859 (15)	0.8328 (3)	0.23683 (14)	0.0421 (8)
C15	0.21895 (16)	0.7021 (4)	0.12503 (15)	0.0497 (9)
C16	0.12504 (17)	0.6799 (4)	0.07740 (16)	0.0628 (11)
H16A	0.1339	0.6644	0.0437	0.075*
H16B	0.1152	0.7735	0.0786	0.075*
C17	0.07719 (17)	0.5918 (4)	0.07894 (17)	0.0657 (12)
H17A	0.0871	0.4996	0.0768	0.098*
H17B	0.0447	0.6130	0.0483	0.098*
H17C	0.0692	0.6067	0.1128	0.098*
C18	0.33220 (14)	0.6775 (3)	0.11775 (14)	0.0424 (8)
C19	0.30544 (14)	0.5753 (3)	0.03056 (13)	0.0432 (8)
H19A	0.3411	0.5476	0.0272	0.052*
H19B	0.2968	0.6645	0.0151	0.052*
C20	0.26011 (17)	0.4782 (4)	0.00121 (18)	0.0605 (10)
H20A	0.2734	0.3881	0.0099	0.091*
H20B	0.2500	0.4921	−0.0379	0.091*
H20C	0.2279	0.4923	0.0129	0.091*
C21	0.15219 (16)	0.1911 (4)	0.11432 (16)	0.0559 (10)
H21	0.1291	0.2444	0.1309	0.067*
C22	0.39673 (16)	0.0839 (4)	0.12375 (18)	0.0604 (11)
H22	0.3909	−0.0128	0.1259	0.072*
Cl1	0.17877 (4)	0.05897 (10)	0.15544 (4)	0.0609 (3)
Cl2	0.20112 (4)	0.29563 (9)	0.09979 (4)	0.0610 (3)
Cl3	0.11045 (4)	0.12829 (10)	0.05171 (4)	0.0526 (2)
Cl4	0.46245 (4)	0.11486 (10)	0.16748 (4)	0.0582 (3)
Cl5	0.39554 (4)	0.11434 (9)	0.05641 (3)	0.0474 (2)
Cl6	0.34815 (4)	0.15914 (10)	0.14836 (4)	0.0587 (3)
N1	0.34921 (11)	0.5394 (3)	0.20164 (10)	0.0368 (6)
N2	0.35097 (12)	0.7837 (3)	0.20939 (11)	0.0436 (7)
N3	0.25981 (11)	0.5373 (3)	0.19819 (11)	0.0402 (6)
H3A	0.2326	0.5111	0.2044	0.048*
N4	0.26743 (11)	0.7741 (3)	0.21767 (11)	0.0431 (7)
H4	0.2417	0.7945	0.2281	0.052*
O1	0.31673 (11)	0.3607 (2)	0.23847 (10)	0.0513 (6)
O2	0.33167 (11)	0.9206 (3)	0.27305 (11)	0.0577 (7)
O3	0.22442 (11)	0.7750 (3)	0.09041 (10)	0.0571 (7)
O4	0.17156 (12)	0.6475 (2)	0.12388 (11)	0.0616 (8)
O5	0.35524 (11)	0.7680 (2)	0.10275 (9)	0.0488 (6)
O6	0.30746 (10)	0.5740 (2)	0.08855 (9)	0.0468 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.064 (3)	0.060 (2)	0.055 (2)	0.006 (2)	0.004 (2)	0.0051 (18)
C2	0.043 (2)	0.054 (2)	0.0452 (19)	0.0138 (17)	0.0076 (15)	−0.0043 (16)
C3	0.0242 (16)	0.053 (2)	0.048 (2)	0.0083 (14)	0.0111 (14)	−0.0041 (16)
C4	0.052 (2)	0.061 (2)	0.0409 (19)	0.0082 (17)	0.0182 (17)	−0.0031 (16)
C5	0.043 (2)	0.050 (2)	0.048 (2)	−0.0039 (16)	0.0124 (16)	−0.0067 (16)
C6	0.0418 (19)	0.047 (2)	0.0481 (19)	−0.0147 (15)	0.0120 (16)	−0.0089 (16)
C7	0.050 (2)	0.050 (2)	0.055 (2)	−0.0040 (17)	0.0105 (18)	−0.0009 (17)
C8	0.067 (3)	0.057 (2)	0.068 (3)	−0.010 (2)	0.003 (2)	−0.023 (2)
C9	0.0260 (16)	0.053 (2)	0.0503 (19)	0.0100 (14)	0.0179 (14)	0.0027 (16)
C10	0.064 (2)	0.0329 (16)	0.0285 (15)	−0.0106 (15)	0.0190 (15)	0.0010 (12)
C11	0.049 (2)	0.051 (2)	0.047 (2)	−0.0064 (16)	0.0243 (17)	−0.0010 (15)
C12	0.0406 (18)	0.0365 (17)	0.0448 (19)	0.0006 (15)	0.0140 (15)	−0.0020 (15)
C13	0.057 (2)	0.0290 (16)	0.0403 (18)	−0.0098 (15)	0.0188 (16)	−0.0003 (13)
C14	0.0478 (19)	0.0326 (16)	0.0456 (19)	−0.0003 (15)	0.0142 (16)	−0.0041 (14)
C15	0.052 (2)	0.046 (2)	0.047 (2)	0.0046 (17)	0.0111 (17)	0.0116 (17)
C16	0.058 (2)	0.062 (2)	0.045 (2)	−0.0162 (19)	−0.0160 (19)	0.0121 (17)
C17	0.055 (2)	0.066 (3)	0.055 (2)	−0.005 (2)	−0.0115 (19)	0.0224 (19)
C18	0.0442 (19)	0.0481 (19)	0.0459 (19)	−0.0069 (15)	0.0300 (16)	0.0055 (15)
C19	0.050 (2)	0.050 (2)	0.0374 (18)	−0.0050 (16)	0.0244 (16)	−0.0165 (14)
C20	0.058 (2)	0.058 (2)	0.065 (2)	−0.028 (2)	0.019 (2)	−0.012 (2)
C21	0.053 (2)	0.056 (2)	0.061 (2)	0.0108 (18)	0.0215 (19)	0.0131 (19)
C22	0.054 (2)	0.052 (2)	0.076 (3)	−0.0040 (18)	0.024 (2)	−0.023 (2)
Cl1	0.0627 (6)	0.0517 (6)	0.0631 (6)	−0.0143 (4)	0.0129 (5)	−0.0136 (4)
Cl2	0.0538 (6)	0.0522 (5)	0.0611 (6)	−0.0158 (4)	−0.0043 (5)	0.0122 (4)
Cl3	0.0594 (6)	0.0606 (5)	0.0414 (5)	−0.0110 (4)	0.0212 (4)	−0.0075 (4)
Cl4	0.0534 (5)	0.0502 (5)	0.0651 (6)	−0.0143 (4)	0.0106 (5)	−0.0133 (4)
Cl5	0.0534 (5)	0.0502 (5)	0.0399 (4)	−0.0050 (4)	0.0164 (4)	−0.0014 (4)
Cl6	0.0576 (6)	0.0570 (6)	0.0609 (6)	−0.0085 (4)	0.0182 (5)	−0.0079 (4)
N1	0.0335 (14)	0.0388 (14)	0.0392 (15)	0.0027 (11)	0.0130 (11)	0.0016 (11)
N2	0.0427 (16)	0.0490 (17)	0.0391 (15)	−0.0099 (13)	0.0132 (13)	−0.0047 (12)
N3	0.0391 (15)	0.0414 (15)	0.0432 (16)	−0.0022 (12)	0.0172 (12)	0.0134 (12)
N4	0.0307 (14)	0.0516 (17)	0.0478 (16)	−0.0001 (12)	0.0134 (12)	−0.0110 (13)
O1	0.0594 (15)	0.0409 (13)	0.0532 (14)	0.0032 (12)	0.0173 (12)	0.0122 (11)
O2	0.0556 (16)	0.0558 (16)	0.0661 (17)	−0.0095 (12)	0.0256 (14)	−0.0253 (13)
O3	0.0632 (17)	0.0522 (16)	0.0521 (15)	0.0148 (13)	0.0130 (13)	0.0146 (12)
O4	0.0663 (18)	0.0439 (14)	0.0562 (16)	−0.0158 (12)	−0.0063 (14)	0.0206 (12)
O5	0.0626 (15)	0.0484 (14)	0.0465 (13)	−0.0225 (12)	0.0330 (12)	0.0000 (11)
O6	0.0592 (16)	0.0479 (14)	0.0385 (13)	−0.0065 (11)	0.0230 (11)	−0.0076 (10)

Geometric parameters (Å, º)

C1—C2	1.503 (5)	C13—C15	1.525 (5)
C1—H1A	0.9600	C14—O2	1.241 (4)
C1—H1B	0.9600	C14—N2	1.328 (4)
C1—H1C	0.9600	C14—N4	1.358 (4)
C2—C7	1.396 (5)	C15—O3	1.187 (4)
C2—C3	1.413 (5)	C15—O4	1.305 (5)
C3—C4	1.353 (5)	C16—O4	1.416 (4)
C3—H3	0.9300	C16—C17	1.503 (5)
C4—C5	1.405 (5)	C16—H16A	0.9700
C4—C9	1.505 (5)	C16—H16B	0.9700
C5—C6	1.386 (5)	C17—H17A	0.9600
C5—C11	1.545 (5)	C17—H17B	0.9600
C6—C7	1.396 (5)	C17—H17C	0.9600
C6—H6	0.9300	C18—O5	1.200 (4)
C7—C8	1.545 (5)	C18—O6	1.310 (4)
C8—H8A	0.9600	C19—O6	1.467 (4)
C8—H8B	0.9600	C19—C20	1.504 (5)
C8—H8C	0.9600	C19—H19A	0.9700
C9—N1	1.440 (4)	C19—H19B	0.9700
C9—H9A	0.9700	C20—H20A	0.9600
C9—H9B	0.9700	C20—H20B	0.9600
C10—N2	1.431 (4)	C20—H20C	0.9600
C10—N1	1.471 (4)	C21—Cl1	1.686 (4)
C10—C18	1.563 (4)	C21—Cl3	1.729 (4)
C10—C13	1.583 (5)	C21—Cl2	1.743 (4)
C11—N2	1.456 (4)	C21—H21	0.9800
C11—H11A	0.9700	C22—Cl4	1.706 (4)
C11—H11B	0.9700	C22—Cl6	1.717 (4)
C12—O1	1.226 (4)	C22—Cl5	1.739 (4)
C12—N3	1.351 (4)	C22—H22	0.9800
C12—N1	1.366 (4)	N3—H3A	0.7960
C13—N3	1.425 (4)	N4—H4	0.8037
C13—N4	1.426 (4)
C2—C1—H1A	109.5	O2—C14—N4	124.7 (3)
C2—C1—H1B	109.5	N2—C14—N4	108.9 (3)
H1A—C1—H1B	109.5	O3—C15—O4	124.2 (4)
C2—C1—H1C	109.5	O3—C15—C13	124.8 (3)
H1A—C1—H1C	109.5	O4—C15—C13	110.8 (3)
H1B—C1—H1C	109.5	O4—C16—C17	107.6 (3)
C7—C2—C3	117.6 (3)	O4—C16—H16A	110.2
C7—C2—C1	121.3 (3)	C17—C16—H16A	110.2
C3—C2—C1	121.1 (3)	O4—C16—H16B	110.2
C4—C3—C2	122.9 (3)	C17—C16—H16B	110.2
C4—C3—H3	118.6	H16A—C16—H16B	108.5
C2—C3—H3	118.6	C16—C17—H17A	109.5
C3—C4—C5	119.1 (3)	C16—C17—H17B	109.5
C3—C4—C9	121.1 (3)	H17A—C17—H17B	109.5
C5—C4—C9	119.7 (3)	C16—C17—H17C	109.5
C6—C5—C4	119.5 (3)	H17A—C17—H17C	109.5
C6—C5—C11	120.4 (3)	H17B—C17—H17C	109.5
C4—C5—C11	120.1 (3)	O5—C18—O6	127.0 (3)
C5—C6—C7	121.0 (3)	O5—C18—C10	123.3 (3)
C5—C6—H6	119.5	O6—C18—C10	109.7 (2)
C7—C6—H6	119.5	O6—C19—C20	105.9 (3)
C6—C7—C2	119.8 (3)	O6—C19—H19A	110.5
C6—C7—C8	118.3 (3)	C20—C19—H19A	110.5
C2—C7—C8	121.9 (3)	O6—C19—H19B	110.5
C7—C8—H8A	109.5	C20—C19—H19B	110.5
C7—C8—H8B	109.5	H19A—C19—H19B	108.7
H8A—C8—H8B	109.5	C19—C20—H20A	109.5
C7—C8—H8C	109.5	C19—C20—H20B	109.5
H8A—C8—H8C	109.5	H20A—C20—H20B	109.5
H8B—C8—H8C	109.5	C19—C20—H20C	109.5
N1—C9—C4	111.3 (3)	H20A—C20—H20C	109.5
N1—C9—H9A	109.4	H20B—C20—H20C	109.5
C4—C9—H9A	109.4	Cl1—C21—Cl3	107.3 (2)
N1—C9—H9B	109.4	Cl1—C21—Cl2	115.6 (2)
C4—C9—H9B	109.4	Cl3—C21—Cl2	106.4 (2)
H9A—C9—H9B	108.0	Cl1—C21—H21	109.1
N2—C10—N1	114.8 (3)	Cl3—C21—H21	109.1
N2—C10—C18	111.5 (3)	Cl2—C21—H21	109.1
N1—C10—C18	108.9 (3)	Cl4—C22—Cl6	109.8 (2)
N2—C10—C13	102.8 (3)	Cl4—C22—Cl5	108.9 (2)
N1—C10—C13	103.6 (2)	Cl6—C22—Cl5	119.8 (3)
C18—C10—C13	115.0 (3)	Cl4—C22—H22	105.8
N2—C11—C5	114.5 (3)	Cl6—C22—H22	105.8
N2—C11—H11A	108.6	Cl5—C22—H22	105.8
C5—C11—H11A	108.6	C12—N1—C9	126.4 (3)
N2—C11—H11B	108.6	C12—N1—C10	109.9 (3)
C5—C11—H11B	108.6	C9—N1—C10	122.5 (3)
H11A—C11—H11B	107.6	C14—N2—C10	112.4 (3)
O1—C12—N3	126.2 (3)	C14—N2—C11	120.4 (3)
O1—C12—N1	123.7 (3)	C10—N2—C11	120.7 (3)
N3—C12—N1	110.1 (3)	C12—N3—C13	113.6 (3)
N3—C13—N4	115.3 (3)	C12—N3—H3A	122.0
N3—C13—C15	112.7 (3)	C13—N3—H3A	123.1
N4—C13—C15	109.0 (3)	C14—N4—C13	113.3 (3)
N3—C13—C10	101.9 (3)	C14—N4—H4	123.1
N4—C13—C10	101.2 (3)	C13—N4—H4	123.5
C15—C13—C10	116.3 (3)	C15—O4—C16	115.6 (3)
O2—C14—N2	126.4 (3)	C18—O6—C19	115.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O2^i	0.80	2.09	2.880 (4)	172
N4—H4···O1^ii	0.80	2.03	2.833 (4)	173

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2.