Diethyl 1,4-dioxo-6-(3-pyrid­yl)perhydro-2,3,4a,6,7a-penta­azacyclo­penta­[cd]indene-2a,7b-dicarboxyl­ate 1,2-dichoroethane solvate

Cao, L.; Wang, Z.; Hu, Y.

doi:10.1107/S1600536807054566

Buy article online - an online subscription or single-article purchase is required to access this article.

Diethyl 1,4-dioxo-6-(3-pyridyl)perhydro-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-2a,7b-dicarboxylate 1,2-dichoroethane solvate

L. Cao, Z. Wang and Y. Hu

The main residue of the title compound, C₁₈H₂₂N₆O₆·C₂H₄Cl₂, is a derivative of glycoluril. The six-membered heterocycle adopts a chair conformation and shares two N atoms with two five-membered rings of the glycoluril unit to form the flexible sidewalls of a molecular clip. Two ethyl fragments and the solvent molecule are disordered; the site occupancy factors for the ethyl groups are 0.72/0.28 and 0.75/0.25 and for the solvent molecule 0.54/0.46. Intermolecular N—H

O and N—H

N hydrogen bonds link the cyclopenta[cd]indene molecules into two-dimensional layers parallel to the bc plane.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054566/cv2321sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054566/cv2321Isup2.hkl Contains datablock I

CCDC reference: 672816

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.072
wR factor = 0.225
Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.82 Ratio

Author Response: This is due to disorder in main residue

PLAT432_ALERT_2_A Short Inter X...Y Contact  C8     ..  C12'    ..       2.85 Ang.

Author Response: This is due to disorder in main residue


Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  Cl1'   ..  C8'     ..       3.14 Ang.

Author Response: This is due to disorder in main residue


Alert level C
ABSTY03_ALERT_1_C  The _exptl_absorpt_correction_type has been given as none.
            However values have been given for Tmin and Tmax. Remove
            these if an absorption correction has not been applied.
  From the CIF: _exptl_absorpt_correction_T_min   0.938
  From the CIF: _exptl_absorpt_correction_T_max   0.968
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.65 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         O6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C11'
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C19
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C19'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       C20'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C20
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H16    ..  H12F    ..       2.12 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.60 Deg.
              C8   -C7   -H7C     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.50 Deg.
              H7A  -C7   -H7D     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      39.10 Deg.
              C7   -C8   -H7C     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.00 Deg.
              C11  -O6   -C11'    1.555   1.555   1.555

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         26

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In 1905, Behrend reported that the condensation of glycoluril and formaldehyde in dilute HCl yielded an insoluble polymeric material now known as Behrend's polymer (Behrend et al., 1905). Glycoluril and its derivatives have during the past two decades established an impressive career as building blocks for supramolecular chemistry (Freeman et al., 1981; Rebek, 2005; Rowan et al., 1999; Wu et al., 2002). As a part of our ongoing investigation into glycoluril derivatives (Li et al., 2006), we report here the structure of the title compound, 1,2-dichoroethane solvate of (I) (Fig. 1).

The molecular structure of the main residue, (I), and solvent molecule are shown in Fig. 1. Molecule (I) has three fused rings, namely, two nearly planar imidazole five-membered rings that adopt envelope conformation with the C═ O groups at the flap position and one non-planar triazine six-membered ring that adopts a chair conformation.

In the crystal, the intermolecular N—H···O and N—H···N hydrogen bonds (Table 1) link the molecules of (I) into two-dimensional layers parallel to bc plane.

Related literature top

For details of the synthesis, see: Li et al. (2006). For general backgroud, see: Behrend et al. (1905); Freeman et al. (1981); Rebek (2005); Rowan et al. (1999); Wu et al. (2002).

Experimental top

The title compound was synthesized according to the procedure of Li et al. (2006) in 45% isolated yield. Crystals for X-ray data collection were obtained by slow evaporation of a 1,2-dichoroethane and methanol solution in a ratio of 4:1 at 293 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. A content of asymmetric unit of the title compound, showing the atomic numbering and displacement ellipsoids at the 10% probability level. H atoms are represented by spheres of arbitrary radius. Only major parts of disordered fragments are shown.

Diethyl 1,4-dioxo-6-(3-pyridyl)perhydro-2,3,4a,6,7a-pentaazacyclopenta[cd]indene- 2a,7 b-dicarboxylate 1,2-dichoroethane solvate top

Crystal data top

C₁₈H₂₂N₆O₆·C₂H₄Cl₂	F(000) = 1080
M_r = 517.37	D_x = 1.468 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2658 reflections
a = 12.9023 (9) Å	θ = 2.3–21.1°
b = 16.4032 (11) Å	µ = 0.33 mm⁻¹
c = 12.1719 (8) Å	T = 294 K
β = 114.657 (1)°	Block, colourless
V = 2341.2 (3) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2684 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ϕ and ω scans	h = −15→12
13883 measured reflections	k = −19→19
4114 independent reflections	l = −14→14

Refinement top

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.225	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1319P)²] where P = (F_o² + 2F_c²)/3
4114 reflections	(Δ/σ)_max < 0.001
359 parameters	Δρ_max = 0.35 e Å⁻³
26 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₈H₂₂N₆O₆·C₂H₄Cl₂	V = 2341.2 (3) Å³
M_r = 517.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9023 (9) Å	µ = 0.33 mm⁻¹
b = 16.4032 (11) Å	T = 294 K
c = 12.1719 (8) Å	0.20 × 0.10 × 0.10 mm
β = 114.657 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2684 reflections with I > 2σ(I)
13883 measured reflections	R_int = 0.058
4114 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	26 restraints
wR(F²) = 0.225	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
4114 reflections	Δρ_min = −0.46 e Å⁻³
359 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C19	0.4234 (19)	0.4751 (19)	0.346 (3)	0.30 (2)	0.458 (10)
H19A	0.4754	0.4958	0.4241	0.30*	0.458 (10)
H19B	0.4679	0.4570	0.3028	0.30*	0.458 (10)
C1	0.5988 (3)	0.24533 (17)	0.1119 (3)	0.0434 (8)
H1A	0.5250	0.2406	0.0438	0.052*
H1B	0.6482	0.2039	0.1028	0.052*
C2	0.6934 (3)	0.24312 (19)	0.3264 (3)	0.0490 (9)
H2A	0.7476	0.2025	0.3252	0.059*
H2B	0.6830	0.2356	0.4002	0.059*
C3	0.5798 (3)	0.39281 (18)	0.0564 (3)	0.0440 (8)
C4	0.7221 (3)	0.3900 (2)	0.3877 (3)	0.0496 (9)
C5	0.7473 (3)	0.35055 (18)	0.2168 (3)	0.0398 (7)
C6	0.8552 (3)	0.3164 (2)	0.2086 (3)	0.0502 (9)
C7	0.9642 (4)	0.3216 (4)	0.0915 (5)	0.1029 (18)
H7A	0.9511	0.2693	0.0508	0.10*	0.720 (9)
H7B	1.0312	0.3174	0.1676	0.10*	0.720 (9)
H7C	0.9487	0.3301	0.0072	0.10*	0.280 (9)
H7D	0.9793	0.2641	0.1092	0.10*	0.280 (9)
C8	0.9803 (9)	0.3879 (6)	0.0128 (10)	0.139 (4)	0.720 (9)
H8A	0.9284	0.3790	−0.0699	0.14*	0.720 (9)
H8B	1.0572	0.3863	0.0199	0.14*	0.720 (9)
H8C	0.9656	0.4402	0.0388	0.14*	0.720 (9)
C8'	1.0650 (19)	0.3728 (16)	0.146 (3)	0.139 (4)	0.280 (9)
H8'1	1.0879	0.3756	0.2317	0.14*	0.280 (9)
H8'2	1.0479	0.4266	0.1121	0.14*	0.280 (9)
H8'3	1.1258	0.3499	0.1299	0.14*	0.280 (9)
C9	0.7366 (3)	0.44625 (18)	0.2187 (3)	0.0439 (8)
C10	0.8353 (3)	0.4977 (2)	0.2176 (3)	0.0545 (9)
C11	1.0337 (10)	0.5246 (6)	0.3268 (11)	0.103 (3)	0.754 (11)
H11A	1.0406	0.5275	0.2506	0.10*	0.754 (11)
H11B	1.1006	0.4970	0.3850	0.10*	0.754 (11)
C12	1.0264 (11)	0.6081 (6)	0.3702 (13)	0.192 (5)	0.754 (11)
H12A	0.9529	0.6309	0.3216	0.19*	0.754 (11)
H12B	1.0847	0.6416	0.3641	0.19*	0.754 (11)
H12C	1.0368	0.6056	0.4530	0.19*	0.754 (11)
C11'	1.019 (4)	0.543 (2)	0.333 (3)	0.103 (3)	0.246 (11)
H11C	1.0947	0.5202	0.3755	0.10*	0.246 (11)
H11D	1.0094	0.5860	0.3833	0.10*	0.246 (11)
C12'	1.006 (3)	0.5791 (19)	0.211 (3)	0.192 (5)	0.246 (11)
H12D	0.9722	0.5391	0.1486	0.19*	0.246 (11)
H12E	1.0799	0.5938	0.2157	0.19*	0.246 (11)
H12F	0.9584	0.6265	0.1927	0.19*	0.246 (11)
C13	0.4906 (3)	0.2760 (2)	0.2311 (3)	0.0488 (8)
H13A	0.4957	0.3327	0.2112	0.059*
H13B	0.4967	0.2738	0.3132	0.059*
C14	0.3768 (3)	0.24205 (19)	0.1459 (3)	0.0454 (8)
C15	0.2997 (3)	0.2838 (2)	0.0490 (3)	0.0596 (10)
H15	0.3170	0.3358	0.0311	0.072*
C16	0.1963 (3)	0.2484 (2)	−0.0223 (4)	0.0684 (11)
H16	0.1429	0.2764	−0.0880	0.082*
C17	0.1738 (3)	0.1718 (2)	0.0053 (4)	0.0645 (11)
H17	0.1040	0.1484	−0.0432	0.077*
C18	0.3455 (3)	0.1646 (2)	0.1670 (3)	0.0559 (9)
H18	0.3966	0.1359	0.2334	0.067*
C20	0.348 (2)	0.5359 (12)	0.281 (2)	0.191 (10)	0.458 (10)
H20A	0.3948	0.5781	0.2682	0.19*	0.458 (10)
H20B	0.3185	0.5588	0.3352	0.19*	0.458 (10)
C19'	0.353 (2)	0.4923 (11)	0.3537 (19)	0.177 (9)	0.542 (10)
H19C	0.2866	0.5249	0.3050	0.18*	0.542 (10)
H19D	0.3791	0.5102	0.4370	0.18*	0.542 (10)
C20'	0.4474 (14)	0.5059 (9)	0.3103 (15)	0.145 (7)	0.542 (10)
H20C	0.5008	0.4608	0.3308	0.145*	0.542 (10)
H20D	0.4881	0.5567	0.3397	0.145*	0.542 (10)
Cl1	0.3467 (12)	0.3958 (6)	0.3638 (8)	0.194 (5)	0.458 (10)
Cl2	0.2351 (10)	0.5258 (4)	0.1477 (5)	0.204 (6)	0.458 (10)
Cl1'	0.3153 (13)	0.3950 (6)	0.3439 (13)	0.285 (8)	0.542 (10)
Cl2'	0.3591 (9)	0.5093 (2)	0.1587 (5)	0.177 (4)	0.542 (10)
N1	0.2469 (3)	0.12886 (18)	0.0982 (3)	0.0627 (9)
N2	0.5853 (2)	0.23011 (15)	0.2236 (2)	0.0428 (7)
N3	0.6469 (2)	0.32622 (14)	0.1092 (2)	0.0380 (6)
N4	0.7410 (2)	0.32533 (14)	0.3273 (2)	0.0418 (7)
N5	0.6352 (2)	0.46129 (16)	0.1113 (3)	0.0544 (8)
H5	0.6118	0.5094	0.0844	0.065*
N6	0.7249 (2)	0.45955 (16)	0.3290 (2)	0.0533 (8)
H6	0.7201	0.5073	0.3556	0.064*
O1	0.4855 (2)	0.38855 (13)	−0.0294 (2)	0.0559 (7)
O2	0.7055 (3)	0.38493 (16)	0.4792 (2)	0.0753 (9)
O3	0.9188 (2)	0.26940 (19)	0.2803 (3)	0.0830 (9)
O4	0.8647 (2)	0.34583 (18)	0.1125 (2)	0.0712 (8)
O5	0.8239 (3)	0.54950 (18)	0.1454 (3)	0.0846 (10)
O6	0.9320 (2)	0.47937 (16)	0.3110 (3)	0.0705 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C19	0.31 (6)	0.30 (7)	0.29 (5)	0.00 (4)	0.14 (5)	−0.01 (5)
C1	0.0462 (19)	0.0367 (16)	0.0449 (18)	−0.0002 (14)	0.0168 (16)	−0.0029 (14)
C2	0.053 (2)	0.0409 (17)	0.0445 (19)	−0.0002 (15)	0.0114 (17)	0.0092 (14)
C3	0.045 (2)	0.0413 (17)	0.0375 (18)	0.0022 (14)	0.0093 (17)	0.0071 (14)
C4	0.054 (2)	0.053 (2)	0.0408 (19)	−0.0112 (16)	0.0190 (18)	−0.0049 (15)
C5	0.0342 (17)	0.0398 (16)	0.0399 (17)	0.0013 (13)	0.0101 (14)	0.0041 (13)
C6	0.042 (2)	0.054 (2)	0.052 (2)	0.0006 (16)	0.0157 (18)	0.0011 (17)
C7	0.076 (3)	0.150 (5)	0.108 (4)	0.018 (3)	0.063 (3)	0.007 (3)
C8	0.134 (9)	0.160 (8)	0.176 (9)	−0.044 (6)	0.116 (8)	−0.033 (7)
C8'	0.134 (9)	0.160 (8)	0.176 (9)	−0.044 (6)	0.116 (8)	−0.033 (7)
C9	0.0421 (19)	0.0399 (16)	0.0415 (18)	−0.0001 (14)	0.0092 (15)	0.0056 (13)
C10	0.053 (2)	0.0460 (19)	0.057 (2)	−0.0039 (16)	0.0147 (19)	0.0068 (17)
C11	0.055 (4)	0.088 (6)	0.139 (5)	−0.020 (5)	0.014 (3)	0.023 (4)
C12	0.157 (9)	0.148 (8)	0.236 (11)	−0.009 (7)	0.048 (9)	−0.033 (8)
C11'	0.055 (4)	0.088 (6)	0.139 (5)	−0.020 (5)	0.014 (3)	0.023 (4)
C12'	0.157 (9)	0.148 (8)	0.236 (11)	−0.009 (7)	0.048 (9)	−0.033 (8)
C13	0.056 (2)	0.0442 (17)	0.049 (2)	−0.0032 (15)	0.0244 (18)	−0.0043 (15)
C14	0.047 (2)	0.0416 (17)	0.0496 (19)	−0.0017 (15)	0.0218 (17)	0.0000 (15)
C15	0.059 (2)	0.0439 (18)	0.069 (2)	0.0009 (17)	0.020 (2)	0.0131 (17)
C16	0.056 (3)	0.057 (2)	0.072 (3)	0.0049 (19)	0.006 (2)	0.014 (2)
C17	0.046 (2)	0.061 (2)	0.069 (3)	−0.0062 (18)	0.007 (2)	0.000 (2)
C18	0.055 (2)	0.052 (2)	0.054 (2)	−0.0024 (17)	0.0152 (19)	0.0075 (16)
C20	0.19 (3)	0.19 (3)	0.19 (3)	0.01 (2)	0.08 (2)	−0.003 (18)
C19'	0.19 (2)	0.16 (2)	0.180 (19)	0.026 (17)	0.079 (17)	−0.027 (15)
C20'	0.165 (15)	0.060 (7)	0.187 (18)	−0.044 (9)	0.051 (14)	−0.009 (8)
Cl1	0.292 (10)	0.208 (9)	0.166 (5)	0.138 (8)	0.180 (6)	0.093 (5)
Cl2	0.250 (11)	0.163 (5)	0.131 (4)	−0.074 (6)	0.013 (5)	0.025 (3)
Cl1'	0.368 (13)	0.199 (9)	0.458 (17)	0.014 (7)	0.342 (13)	0.091 (8)
Cl2'	0.290 (10)	0.112 (3)	0.167 (4)	−0.010 (3)	0.134 (6)	0.017 (2)
N1	0.058 (2)	0.0494 (17)	0.070 (2)	−0.0098 (15)	0.0156 (18)	0.0085 (15)
N2	0.0431 (16)	0.0396 (14)	0.0403 (15)	−0.0009 (11)	0.0119 (13)	0.0013 (11)
N3	0.0371 (14)	0.0378 (13)	0.0338 (13)	0.0005 (11)	0.0095 (12)	0.0037 (11)
N4	0.0445 (16)	0.0393 (14)	0.0339 (14)	−0.0030 (11)	0.0085 (12)	0.0045 (11)
N5	0.0477 (17)	0.0368 (14)	0.0565 (18)	0.0019 (12)	−0.0004 (14)	0.0115 (13)
N6	0.063 (2)	0.0413 (15)	0.0565 (18)	−0.0040 (13)	0.0256 (16)	−0.0062 (13)
O1	0.0483 (15)	0.0497 (13)	0.0466 (14)	0.0023 (11)	−0.0032 (12)	0.0108 (10)
O2	0.105 (2)	0.0729 (18)	0.0578 (17)	−0.0234 (15)	0.0442 (17)	−0.0146 (13)
O3	0.0560 (18)	0.093 (2)	0.093 (2)	0.0292 (15)	0.0242 (16)	0.0342 (17)
O4	0.0566 (17)	0.095 (2)	0.0707 (18)	0.0124 (14)	0.0348 (15)	0.0108 (15)
O5	0.078 (2)	0.0799 (19)	0.087 (2)	−0.0123 (15)	0.0253 (18)	0.0347 (17)
O6	0.0419 (15)	0.0689 (17)	0.0802 (19)	−0.0131 (12)	0.0053 (14)	0.0163 (14)

Geometric parameters (Å, º) top

C19—C20	1.388 (18)	C10—O6	1.325 (4)
C19—Cl1	1.70 (2)	C11—O6	1.449 (9)
C19—H19A	0.9700	C11—C12	1.485 (9)
C19—H19B	0.9700	C11—H11A	0.9700
C1—N2	1.463 (4)	C11—H11B	0.9700
C1—N3	1.471 (4)	C12—H12A	0.9600
C1—H1A	0.9700	C12—H12B	0.9600
C1—H1B	0.9700	C12—H12C	0.9600
C2—N2	1.449 (4)	C11'—O6	1.48 (2)
C2—N4	1.480 (4)	C11'—C12'	1.542 (11)
C2—H2A	0.9700	C11'—H11C	0.9700
C2—H2B	0.9700	C11'—H11D	0.9700
C3—O1	1.231 (4)	C12'—H12D	0.9600
C3—N5	1.349 (4)	C12'—H12E	0.9600
C3—N3	1.375 (4)	C12'—H12F	0.9600
C4—O2	1.222 (4)	C13—N2	1.470 (4)
C4—N6	1.355 (4)	C13—C14	1.507 (5)
C4—N4	1.368 (4)	C13—H13A	0.9700
C5—N4	1.442 (4)	C13—H13B	0.9700
C5—N3	1.462 (4)	C14—C15	1.368 (5)
C5—C6	1.542 (5)	C14—C18	1.389 (5)
C5—C9	1.577 (4)	C15—C16	1.380 (5)
C6—O3	1.197 (4)	C15—H15	0.9300
C6—O4	1.318 (4)	C16—C17	1.362 (5)
C7—C8'	1.455 (16)	C16—H16	0.9300
C7—O4	1.464 (5)	C17—N1	1.333 (5)
C7—C8	1.519 (9)	C17—H17	0.9300
C7—H7A	0.9700	C18—N1	1.332 (4)
C7—H7B	0.9700	C18—H18	0.9300
C7—H7C	0.9700	C20—Cl2	1.672 (17)
C7—H7D	0.9700	C20—H20A	0.9700
C8—H7C	1.0229	C20—H20B	0.9700
C8—H8A	0.9600	C19'—C20'	1.538 (17)
C8—H8B	0.9600	C19'—Cl1'	1.658 (17)
C8—H8C	0.9600	C19'—H19C	0.9700
C8'—H8'1	0.9600	C19'—H19D	0.9700
C8'—H8'2	0.9600	C20'—Cl2'	1.718 (16)
C8'—H8'3	0.9600	C20'—H20C	0.9700
C9—N6	1.428 (4)	C20'—H20D	0.9700
C9—N5	1.433 (4)	N5—H5	0.8600
C9—C10	1.532 (5)	N6—H6	0.8600
C10—O5	1.187 (4)

C20—C19—Cl1	108.4 (18)	O6—C11—H11A	109.8
C20—C19—H19A	110.0	C12—C11—H11A	109.8
Cl1—C19—H19A	110.0	O6—C11—H11B	109.8
C20—C19—H19B	110.0	C12—C11—H11B	109.8
Cl1—C19—H19B	110.0	H11A—C11—H11B	108.3
H19A—C19—H19B	108.4	O6—C11'—C12'	109.0 (17)
N2—C1—N3	112.9 (2)	O6—C11'—H11C	109.9
N2—C1—H1A	109.0	C12'—C11'—H11C	109.9
N3—C1—H1A	109.0	O6—C11'—H11D	109.9
N2—C1—H1B	109.0	C12'—C11'—H11D	109.9
N3—C1—H1B	109.0	H11C—C11'—H11D	108.3
H1A—C1—H1B	107.8	C11'—C12'—H12D	109.5
N2—C2—N4	112.8 (2)	C11'—C12'—H12E	109.5
N2—C2—H2A	109.0	H12D—C12'—H12E	109.5
N4—C2—H2A	109.0	C11'—C12'—H12F	109.5
N2—C2—H2B	109.0	H12D—C12'—H12F	109.5
N4—C2—H2B	109.0	H12E—C12'—H12F	109.5
H2A—C2—H2B	107.8	N2—C13—C14	111.4 (3)
O1—C3—N5	126.8 (3)	N2—C13—H13A	109.4
O1—C3—N3	123.9 (3)	C14—C13—H13A	109.4
N5—C3—N3	109.2 (3)	N2—C13—H13B	109.4
O2—C4—N6	126.2 (3)	C14—C13—H13B	109.4
O2—C4—N4	125.1 (3)	H13A—C13—H13B	108.0
N6—C4—N4	108.7 (3)	C15—C14—C18	117.0 (3)
N4—C5—N3	112.6 (2)	C15—C14—C13	123.9 (3)
N4—C5—C6	111.1 (3)	C18—C14—C13	119.1 (3)
N3—C5—C6	109.2 (2)	C14—C15—C16	119.8 (3)
N4—C5—C9	103.5 (2)	C14—C15—H15	120.1
N3—C5—C9	103.6 (2)	C16—C15—H15	120.1
C6—C5—C9	116.7 (3)	C17—C16—C15	118.8 (3)
O3—C6—O4	126.4 (3)	C17—C16—H16	120.6
O3—C6—C5	123.3 (3)	C15—C16—H16	120.6
O4—C6—C5	110.2 (3)	N1—C17—C16	123.3 (4)
C8'—C7—O4	116.6 (11)	N1—C17—H17	118.4
C8'—C7—C8	62.8 (12)	C16—C17—H17	118.4
O4—C7—C8	106.1 (5)	N1—C18—C14	124.2 (3)
C8'—C7—H7A	132.4	N1—C18—H18	117.9
O4—C7—H7A	110.5	C14—C18—H18	117.9
C8—C7—H7A	110.5	C19—C20—Cl2	127 (2)
C8'—C7—H7B	48.3	C19—C20—H20A	105.6
O4—C7—H7B	110.5	Cl2—C20—H20A	105.6
C8—C7—H7B	110.5	C19—C20—H20B	105.6
H7A—C7—H7B	108.7	Cl2—C20—H20B	105.6
C8'—C7—H7C	98.6	H20A—C20—H20B	106.1
O4—C7—H7C	109.7	C20'—C19'—Cl1'	111.3 (12)
C8—C7—H7C	41.6	C20'—C19'—H19C	109.4
H7A—C7—H7C	70.7	Cl1'—C19'—H19C	109.4
H7B—C7—H7C	136.7	C20'—C19'—H19D	109.4
C8'—C7—H7D	113.7	Cl1'—C19'—H19D	109.4
O4—C7—H7D	109.6	H19C—C19'—H19D	108.0
C8—C7—H7D	140.2	C19'—C20'—Cl2'	96.2 (12)
H7A—C7—H7D	39.5	C19'—C20'—H20C	112.5
H7B—C7—H7D	72.6	Cl2'—C20'—H20C	112.5
H7C—C7—H7D	107.9	C19'—C20'—H20D	112.5
C7—C8—H7C	39.1	Cl2'—C20'—H20D	112.5
C7—C8—H8A	109.5	H20C—C20'—H20D	110.0
H7C—C8—H8A	72.8	C18—N1—C17	116.9 (3)
C7—C8—H8B	109.5	C2—N2—C1	109.4 (3)
H7C—C8—H8B	110.5	C2—N2—C13	113.4 (3)
C7—C8—H8C	109.5	C1—N2—C13	113.2 (2)
H7C—C8—H8C	136.2	C3—N3—C5	110.6 (2)
C7—C8'—H8'1	109.5	C3—N3—C1	122.5 (3)
C7—C8'—H8'2	109.5	C5—N3—C1	116.8 (2)
H8'1—C8'—H8'2	109.5	C4—N4—C5	111.7 (2)
C7—C8'—H8'3	109.5	C4—N4—C2	123.0 (3)
H8'1—C8'—H8'3	109.5	C5—N4—C2	116.0 (2)
H8'2—C8'—H8'3	109.5	C3—N5—C9	113.7 (2)
N6—C9—N5	114.6 (3)	C3—N5—H5	123.2
N6—C9—C10	109.8 (3)	C9—N5—H5	123.2
N5—C9—C10	110.1 (3)	C4—N6—C9	113.8 (3)
N6—C9—C5	102.1 (2)	C4—N6—H6	123.1
N5—C9—C5	102.1 (2)	C9—N6—H6	123.1
C10—C9—C5	118.0 (3)	C6—O4—C7	118.0 (3)
O5—C10—O6	125.4 (3)	C10—O6—C11	118.3 (5)
O5—C10—C9	123.6 (3)	C10—O6—C11'	111.6 (16)
O6—C10—C9	110.8 (3)	C11—O6—C11'	15 (3)
O6—C11—C12	109.3 (9)

N4—C5—C6—O3	6.1 (5)	N4—C5—N3—C3	107.4 (3)
N3—C5—C6—O3	−118.7 (4)	C6—C5—N3—C3	−128.6 (3)
C9—C5—C6—O3	124.4 (4)	C9—C5—N3—C3	−3.7 (3)
N4—C5—C6—O4	−174.5 (3)	N4—C5—N3—C1	−38.9 (3)
N3—C5—C6—O4	60.7 (3)	C6—C5—N3—C1	85.0 (3)
C9—C5—C6—O4	−56.3 (4)	C9—C5—N3—C1	−150.0 (3)
N4—C5—C9—N6	−0.6 (3)	N2—C1—N3—C3	−94.8 (3)
N3—C5—C9—N6	117.1 (2)	N2—C1—N3—C5	47.3 (3)
C6—C5—C9—N6	−122.9 (3)	O2—C4—N4—C5	174.7 (3)
N4—C5—C9—N5	−119.4 (3)	N6—C4—N4—C5	−5.2 (4)
N3—C5—C9—N5	−1.7 (3)	O2—C4—N4—C2	29.4 (5)
C6—C5—C9—N5	118.3 (3)	N6—C4—N4—C2	−150.5 (3)
N4—C5—C9—C10	119.8 (3)	N3—C5—N4—C4	−107.7 (3)
N3—C5—C9—C10	−122.5 (3)	C6—C5—N4—C4	129.4 (3)
C6—C5—C9—C10	−2.5 (4)	C9—C5—N4—C4	3.5 (3)
N6—C9—C10—O5	−118.2 (4)	N3—C5—N4—C2	40.1 (3)
N5—C9—C10—O5	8.9 (5)	C6—C5—N4—C2	−82.7 (3)
C5—C9—C10—O5	125.5 (4)	C9—C5—N4—C2	151.3 (3)
N6—C9—C10—O6	58.3 (4)	N2—C2—N4—C4	93.3 (4)
N5—C9—C10—O6	−174.6 (3)	N2—C2—N4—C5	−50.7 (4)
C5—C9—C10—O6	−58.0 (4)	O1—C3—N5—C9	172.1 (3)
N2—C13—C14—C15	−114.8 (4)	N3—C3—N5—C9	−9.6 (4)
N2—C13—C14—C18	66.8 (4)	N6—C9—N5—C3	−102.7 (3)
C18—C14—C15—C16	0.1 (5)	C10—C9—N5—C3	133.0 (3)
C13—C14—C15—C16	−178.3 (3)	C5—C9—N5—C3	6.8 (4)
C14—C15—C16—C17	−0.6 (6)	O2—C4—N6—C9	−175.0 (4)
C15—C16—C17—N1	0.0 (7)	N4—C4—N6—C9	4.9 (4)
C15—C14—C18—N1	1.0 (5)	N5—C9—N6—C4	107.0 (3)
C13—C14—C18—N1	179.6 (3)	C10—C9—N6—C4	−128.6 (3)
Cl1—C19—C20—Cl2	−53 (5)	C5—C9—N6—C4	−2.6 (3)
Cl1'—C19'—C20'—Cl2'	82.1 (15)	O3—C6—O4—C7	−2.2 (6)
C14—C18—N1—C17	−1.6 (6)	C5—C6—O4—C7	178.5 (3)
C16—C17—N1—C18	1.1 (6)	C8'—C7—O4—C6	−89.6 (15)
N4—C2—N2—C1	55.9 (3)	C8—C7—O4—C6	−156.8 (5)
N4—C2—N2—C13	−71.5 (3)	O5—C10—O6—C11	−1.3 (8)
N3—C1—N2—C2	−54.3 (3)	C9—C10—O6—C11	−177.7 (6)
N3—C1—N2—C13	73.2 (3)	O5—C10—O6—C11'	14 (2)
C14—C13—N2—C2	−162.3 (3)	C9—C10—O6—C11'	−163 (2)
C14—C13—N2—C1	72.3 (3)	C12—C11—O6—C10	73.4 (10)
O1—C3—N3—C5	−173.6 (3)	C12—C11—O6—C11'	6 (5)
N5—C3—N3—C5	8.1 (4)	C12'—C11'—O6—C10	−35 (4)
O1—C3—N3—C1	−29.5 (5)	C12'—C11'—O6—C11	84 (6)
N5—C3—N3—C1	152.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1	0.97	2.56	2.918 (4)	102
C19′—H19D···O2ⁱ	0.97	2.47	3.166 (17)	128
C1—H1B···O2ⁱⁱ	0.97	2.42	3.305 (4)	152
N6—H6···N1ⁱⁱⁱ	0.86	2.07	2.892 (4)	160
N5—H5···O1^iv	0.86	2.03	2.862 (3)	162

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₆O₆·C₂H₄Cl₂
M_r	517.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	12.9023 (9), 16.4032 (11), 12.1719 (8)
β (°)	114.657 (1)
V (Å³)	2341.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13883, 4114, 2684
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.225, 1.04
No. of reflections	4114
No. of parameters	359
No. of restraints	26
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.46

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···N1ⁱ	0.86	2.07	2.892 (4)	160.4
N5—H5···O1ⁱⁱ	0.86	2.03	2.862 (3)	162.3

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Diethyl 1,4-dioxo-6-(3-pyrid­yl)perhydro-2,3,4a,6,7a-penta­azacyclo­penta­[cd]indene-2a,7b-dicarboxyl­ate 1,2-dichoroethane solvate

Supporting information

Key indicators

checkCIF/PLATON results

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

Diethyl 1,4-dioxo-6-(3-pyridyl)perhydro-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-2a,7b-dicarboxylate 1,2-dichoroethane solvate