1-[2-(5-Nitro-1H-benzimidazol-1-yl)ethyl]morpholinium chloride

Akkurt, M.; Türktekin, S.; Küçükbay, H.; Yılmaz, U.; Büyükgüngör, O.

doi:10.1107/S1600536804033240

1-[2-(5-Nitro-1H-benzimidazol-1-yl)ethyl]morpholinium chloride

M. Akkurt, S. Türktekin, H. Küçükbay, U. Yılmaz and O. Büyükgüngör

The title compound, C₁₃H₁₇N₄O⁺·Cl⁻, was synthesized from 1-(2-methoxyethyl)-5-nitrobenzimidazole and N-(2-chloroethyl)morpholine hydrochloride in dimethylformamide. The crystal structure has been determined at 100 K and exhibits an intramolecular N—H

Cl, and intermolecular C—H

Cl and C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033240/lh6336sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033240/lh6336Isup2.hkl Contains datablock I

CCDC reference: 262485

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R factor = 0.027
wR factor = 0.069
Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.01

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

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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-[2-(5-Nitrobenzimidazol-1-yl)ethyl]morpholinium chloride top

Crystal data top

C₁₃H₁₇N₄O₃⁺·Cl⁻	Z = 2
M_r = 312.76	F(000) = 328
Triclinic, P1	D_x = 1.512 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0522 (5) Å	Cell parameters from 23590 reflections
b = 9.9537 (8) Å	θ = 2.8–29.3°
c = 9.9895 (7) Å	µ = 0.30 mm⁻¹
α = 83.607 (6)°	T = 100 K
β = 80.386 (6)°	Prism, colorless
γ = 89.477 (6)°	0.23 × 0.22 × 0.20 mm
V = 687.04 (9) Å³

Data collection top

Stoe IPDS-II diffractometer	3692 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3381 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.027
Detector resolution: 6.67 pixels mm^-1	θ_max = 29.1°, θ_min = 2.8°
ω scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
T_min = 0.935, T_max = 0.943	l = −13→13
14617 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0336P)² + 0.269P] where P = (F_o² + 2F_c²)/3
3692 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted} ^R^-factors ^wR ^{and all goodnesses of fit} ^S ^{are based on} ^F2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of} ^F2 > σ(F^{2) is used only for calculating -}^R^-factor-obs ^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
O1	0.73019 (14)	−0.07010 (8)	0.42335 (10)	0.0276 (3)
O2	0.62749 (13)	0.04722 (8)	0.25601 (9)	0.0241 (3)
O3	0.85763 (11)	0.90840 (7)	−0.21328 (8)	0.0159 (2)
N1	0.78503 (12)	0.51776 (8)	0.58133 (9)	0.0132 (2)
N2	0.70521 (12)	0.53469 (8)	0.37100 (8)	0.0111 (2)
N3	0.69205 (13)	0.03821 (9)	0.36281 (9)	0.0155 (2)
N4	0.74863 (11)	0.70253 (8)	0.01066 (8)	0.0097 (2)
C1	0.77324 (13)	0.38996 (10)	0.54127 (10)	0.0112 (2)
C2	0.80100 (14)	0.26446 (10)	0.61276 (10)	0.0134 (2)
C3	0.77557 (14)	0.14967 (10)	0.55176 (10)	0.0140 (2)
C4	0.72227 (13)	0.16227 (9)	0.42217 (10)	0.0121 (2)
C5	0.69425 (13)	0.28445 (10)	0.34640 (10)	0.0112 (2)
C6	0.72237 (13)	0.39783 (9)	0.40996 (9)	0.0101 (2)
C7	0.74371 (14)	0.59865 (10)	0.47766 (10)	0.0131 (2)
C8	0.64118 (14)	0.60099 (10)	0.24937 (10)	0.0130 (2)
C9	0.79803 (14)	0.60362 (9)	0.12404 (10)	0.0114 (2)
C10	0.85402 (14)	0.67119 (10)	−0.12549 (10)	0.0118 (2)
C11	0.80831 (14)	0.77585 (10)	−0.23740 (10)	0.0136 (2)
C12	0.74573 (15)	0.93997 (10)	−0.08845 (11)	0.0157 (3)
C13	0.79196 (15)	0.84529 (10)	0.03084 (10)	0.0137 (3)
Cl1	0.31412 (3)	0.69009 (2)	0.02117 (2)	0.0131 (1)
H2	0.831 (2)	0.2586 (15)	0.7040 (15)	0.018 (3)*
H3	0.790 (2)	0.0606 (16)	0.5972 (16)	0.022 (4)*
H4	0.621 (2)	0.6956 (15)	0.0111 (15)	0.022 (4)*
H5	0.661 (2)	0.2889 (14)	0.2591 (15)	0.015 (3)*
H7	0.737 (2)	0.6954 (15)	0.4740 (14)	0.016 (3)*
H8A	0.527 (2)	0.5561 (15)	0.2346 (15)	0.019 (3)*
H8B	0.6072 (19)	0.6899 (14)	0.2691 (14)	0.012 (3)*
H9A	0.8047 (19)	0.5160 (14)	0.0913 (14)	0.013 (3)*
H9B	0.922 (2)	0.6314 (14)	0.1411 (14)	0.012 (3)*
H10A	0.815 (2)	0.5832 (15)	−0.1382 (15)	0.018 (3)*
H10B	0.989 (2)	0.6739 (13)	−0.1199 (14)	0.012 (3)*
H11A	0.886 (2)	0.7583 (15)	−0.3240 (15)	0.020 (3)*
H11B	0.6719 (19)	0.7723 (14)	−0.2430 (13)	0.012 (3)*
H12A	0.775 (2)	1.0293 (15)	−0.0755 (15)	0.020 (3)*
H12B	0.608 (2)	0.9332 (14)	−0.0911 (14)	0.016 (3)*
H13A	0.714 (2)	0.8655 (14)	0.1152 (14)	0.016 (3)*
H13B	0.928 (2)	0.8499 (14)	0.0364 (14)	0.016 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0424 (5)	0.0088 (3)	0.0336 (5)	0.0010 (3)	−0.0135 (4)	0.0002 (3)
O2	0.0343 (5)	0.0182 (4)	0.0240 (4)	0.0029 (3)	−0.0134 (3)	−0.0083 (3)
O3	0.0192 (4)	0.0132 (3)	0.0141 (3)	−0.0023 (3)	−0.0018 (3)	0.0027 (3)
N1	0.0139 (4)	0.0127 (4)	0.0127 (4)	−0.0009 (3)	−0.0010 (3)	−0.0020 (3)
N2	0.0128 (4)	0.0092 (4)	0.0107 (4)	0.0006 (3)	−0.0016 (3)	0.0004 (3)
N3	0.0164 (4)	0.0107 (4)	0.0194 (4)	0.0000 (3)	−0.0023 (3)	−0.0023 (3)
N4	0.0099 (3)	0.0086 (3)	0.0104 (3)	0.0002 (3)	−0.0013 (3)	−0.0003 (3)
C1	0.0100 (4)	0.0121 (4)	0.0109 (4)	−0.0008 (3)	−0.0005 (3)	−0.0008 (3)
C2	0.0143 (4)	0.0144 (4)	0.0109 (4)	0.0000 (3)	−0.0026 (3)	0.0014 (3)
C3	0.0148 (4)	0.0119 (4)	0.0144 (4)	0.0009 (3)	−0.0021 (3)	0.0023 (3)
C4	0.0123 (4)	0.0094 (4)	0.0145 (4)	−0.0001 (3)	−0.0013 (3)	−0.0019 (3)
C5	0.0105 (4)	0.0118 (4)	0.0109 (4)	0.0003 (3)	−0.0014 (3)	−0.0004 (3)
C6	0.0090 (4)	0.0101 (4)	0.0102 (4)	0.0004 (3)	−0.0002 (3)	0.0010 (3)
C7	0.0138 (4)	0.0114 (4)	0.0136 (4)	−0.0004 (3)	−0.0003 (3)	−0.0023 (3)
C8	0.0122 (4)	0.0138 (4)	0.0117 (4)	0.0021 (3)	−0.0011 (3)	0.0031 (3)
C9	0.0119 (4)	0.0106 (4)	0.0110 (4)	0.0014 (3)	−0.0016 (3)	0.0017 (3)
C10	0.0125 (4)	0.0116 (4)	0.0106 (4)	0.0013 (3)	−0.0001 (3)	−0.0015 (3)
C11	0.0145 (4)	0.0146 (4)	0.0116 (4)	−0.0001 (3)	−0.0026 (3)	0.0002 (3)
C12	0.0207 (5)	0.0099 (4)	0.0161 (5)	0.0012 (3)	−0.0036 (4)	0.0005 (3)
C13	0.0196 (5)	0.0082 (4)	0.0137 (4)	−0.0013 (3)	−0.0041 (4)	−0.0010 (3)
Cl1	0.0105 (1)	0.0154 (1)	0.0136 (1)	−0.0006 (1)	−0.0029 (1)	−0.0013 (1)

Geometric parameters (Å, º) top

O1—N3	1.2265 (13)	C8—C9	1.5239 (14)
O2—N3	1.2222 (13)	C10—C11	1.5145 (14)
O3—C11	1.4237 (12)	C12—C13	1.5128 (15)
O3—C12	1.4250 (13)	C2—H2	0.965 (15)
N1—C1	1.3826 (13)	C3—H3	0.963 (16)
N1—C7	1.3102 (13)	C5—H5	0.937 (15)
N2—C6	1.3844 (12)	C7—H7	0.961 (15)
N2—C7	1.3657 (13)	C8—H8A	0.965 (14)
N2—C8	1.4543 (13)	C8—H8B	0.948 (14)
N3—C4	1.4601 (13)	C9—H9A	0.963 (14)
N4—C9	1.5002 (12)	C9—H9B	0.967 (14)
N4—C10	1.5007 (13)	C10—H10A	0.949 (15)
N4—C13	1.4985 (13)	C10—H10B	0.964 (14)
N4—H4	0.903 (14)	C11—H11A	0.976 (15)
C1—C2	1.3973 (14)	C11—H11B	0.974 (14)
C1—C6	1.4104 (13)	C12—H12A	0.942 (15)
C2—C3	1.3800 (14)	C12—H12B	0.979 (14)
C3—C4	1.3994 (14)	C13—H13A	0.966 (14)
C4—C5	1.3898 (14)	C13—H13B	0.972 (14)
C5—C6	1.3863 (13)

Cl1···N4	3.0517 (9)	C5···H11Bⁱ	3.017 (14)
Cl1···C8	3.5457 (11)	C5···H10B^xi	2.898 (14)
Cl1···C9ⁱ	3.5562 (10)	C5···H11A^xi	2.962 (14)
Cl1···H13Bⁱⁱ	3.131 (14)	C7···H11A^ix	2.975 (15)
Cl1···H4	2.151 (14)	C8···H13A	2.829 (14)
Cl1···H8A	2.996 (15)	C8···H5	3.100 (14)
Cl1···H10Bⁱⁱ	2.899 (14)	C10···H9A^xi	3.071 (14)
Cl1···H5ⁱ	2.760 (15)	C13···H8B	2.817 (14)
Cl1···H9Bⁱⁱ	2.862 (14)	H2···Cl1ⁱⁱⁱ	2.865 (15)
Cl1···H2ⁱⁱⁱ	2.865 (15)	H3···O3^x	2.399 (16)
Cl1···H12A^iv	2.947 (15)	H3···O1	2.376 (16)
Cl1···H9Aⁱ	2.652 (14)	H4···Cl1	2.151 (14)
Cl1···H10Aⁱ	2.929 (15)	H4···H8A	2.49 (2)
O1···C7^v	3.2845 (13)	H4···H8B	2.56 (2)
O1···C4^vi	3.3909 (14)	H4···H11B	2.535 (19)
O2···C13^v	3.2462 (13)	H4···H12B	2.48 (2)
O2···C12ⁱ	3.3412 (14)	H5···H11Bⁱ	2.47 (2)
O3···N4	2.8684 (11)	H5···O2	2.424 (14)
O3···C3^vii	3.2840 (13)	H5···Cl1ⁱ	2.760 (15)
O1···H7^v	2.334 (15)	H5···C8	3.100 (14)
O1···H3	2.376 (16)	H7···H11A^ix	2.56 (2)
O2···H13A^v	2.425 (14)	H7···O1^xii	2.334 (15)
O2···H5	2.424 (14)	H7···H8B	2.38 (2)
O2···H11Bⁱ	2.770 (14)	H8A···Cl1	2.996 (15)
O2···H12Bⁱ	2.519 (14)	H8A···N1ⁱⁱⁱ	2.672 (15)
O3···H3^vii	2.399 (16)	H8A···C1ⁱⁱⁱ	2.907 (15)
N1···N1^viii	3.2282 (12)	H8A···H4	2.49 (2)
N1···C1^viii	3.2520 (13)	H8B···H7	2.38 (2)
N1···C8ⁱⁱⁱ	3.3487 (13)	H8B···H13A	2.24 (2)
N1···N2	2.2526 (12)	H8B···C13	2.817 (14)
N1···C11^ix	3.3239 (13)	H8B···H4	2.56 (2)
N2···N1	2.2526 (12)	H8B···C2ⁱⁱⁱ	2.974 (14)
N2···C1ⁱⁱⁱ	3.4392 (13)	H8B···C1ⁱⁱⁱ	3.070 (14)
N4···O3	2.8684 (11)	H9A···H10A	2.31 (2)
N4···Cl1	3.0517 (9)	H9A···H10B^xi	2.396 (19)
N1···H11A^ix	2.810 (15)	H9A···Cl1ⁱ	2.652 (14)
N1···H8Aⁱⁱⁱ	2.672 (15)	H9A···C10^xi	3.071 (14)
C1···N2ⁱⁱⁱ	3.4392 (13)	H9B···H10B	2.559 (19)
C1···N1^viii	3.2520 (13)	H9B···Cl1^xiv	2.862 (14)
C1···C8ⁱⁱⁱ	3.3044 (14)	H9B···H13B	2.30 (2)
C1···C7^viii	3.3824 (14)	H10A···H9A	2.31 (2)
C2···C8ⁱⁱⁱ	3.5092 (14)	H10A···Cl1ⁱ	2.929 (15)
C2···C7^viii	3.4378 (14)	H10B···H9B	2.559 (19)
C3···O3^x	3.2840 (13)	H10B···H13B	2.462 (19)
C4···C11^xi	3.5339 (14)	H10B···C5^xi	2.898 (14)
C4···O1^vi	3.3909 (14)	H10B···Cl1^xiv	2.899 (14)
C5···C11^xi	3.5614 (14)	H10B···H9A^xi	2.396 (19)
C5···C7ⁱⁱⁱ	3.5439 (14)	H11A···C4^xi	2.860 (14)
C5···C10^xi	3.5601 (14)	H11A···C7^xiii	2.975 (15)
C6···C7ⁱⁱⁱ	3.2923 (14)	H11A···C5^xi	2.962 (14)
C7···C1^viii	3.3824 (14)	H11A···N1^xiii	2.810 (15)
C7···O1^xii	3.2845 (13)	H11A···H7^xiii	2.56 (2)
C7···C6ⁱⁱⁱ	3.2923 (14)	H11A···C3^xi	3.078 (15)
C7···C5ⁱⁱⁱ	3.5439 (14)	H11B···H12B	2.317 (19)
C7···C2^viii	3.4378 (14)	H11B···H4	2.535 (19)
C8···C1ⁱⁱⁱ	3.3044 (14)	H11B···C5ⁱ	3.017 (14)
C8···C2ⁱⁱⁱ	3.5092 (14)	H11B···H5ⁱ	2.47 (2)
C8···Cl1	3.5457 (11)	H11B···O2ⁱ	2.770 (14)
C8···N1ⁱⁱⁱ	3.3487 (13)	H12A···H13B^xv	2.53 (2)
C9···Cl1ⁱ	3.5562 (10)	H12A···Cl1^iv	2.947 (15)
C10···C5^xi	3.5601 (14)	H12B···H11B	2.317 (19)
C11···N1^xiii	3.3239 (13)	H12B···H4	2.48 (2)
C11···C5^xi	3.5614 (14)	H12B···O2ⁱ	2.519 (14)
C11···C4^xi	3.5339 (14)	H13A···O2^xii	2.425 (14)
C12···O2ⁱ	3.3412 (14)	H13A···C8	2.829 (14)
C13···O2^xii	3.2462 (13)	H13A···H8B	2.24 (2)
C1···H8Aⁱⁱⁱ	2.907 (15)	H13B···H10B	2.462 (19)
C1···H8Bⁱⁱⁱ	3.070 (14)	H13B···H12A^xv	2.53 (2)
C2···H8Bⁱⁱⁱ	2.974 (14)	H13B···Cl1^xiv	3.131 (14)
C3···H11A^xi	3.078 (15)	H13B···H9B	2.30 (2)
C4···H11A^xi	2.860 (14)

C11—O3—C12	109.12 (8)	C4—C3—H3	118.9 (9)
C1—N1—C7	104.00 (8)	C4—C5—H5	122.2 (9)
C6—N2—C7	105.88 (8)	C6—C5—H5	123.3 (9)
C6—N2—C8	128.79 (8)	N1—C7—H7	124.9 (8)
C7—N2—C8	125.08 (8)	N2—C7—H7	120.5 (8)
O1—N3—O2	123.14 (9)	N2—C8—H8A	109.5 (9)
O1—N3—C4	118.49 (9)	N2—C8—H8B	105.8 (8)
O2—N3—C4	118.36 (9)	C9—C8—H8A	110.7 (9)
C9—N4—C10	111.11 (7)	C9—C8—H8B	110.9 (8)
C9—N4—C13	111.83 (7)	H8A—C8—H8B	108.0 (12)
C10—N4—C13	109.43 (7)	N4—C9—H9A	106.8 (8)
C13—N4—H4	107.9 (10)	N4—C9—H9B	106.4 (8)
C9—N4—H4	107.7 (9)	C8—C9—H9A	109.1 (8)
C10—N4—H4	108.8 (9)	C8—C9—H9B	113.0 (8)
N1—C1—C2	129.05 (9)	H9A—C9—H9B	111.1 (12)
N1—C1—C6	110.52 (8)	N4—C10—H10A	107.2 (9)
C2—C1—C6	120.41 (9)	N4—C10—H10B	106.3 (8)
C1—C2—C3	118.15 (9)	C11—C10—H10A	111.6 (9)
C2—C3—C4	119.46 (9)	C11—C10—H10B	110.5 (8)
C3—C4—C5	124.68 (9)	H10A—C10—H10B	111.1 (12)
N3—C4—C5	117.62 (9)	O3—C11—H11A	106.8 (9)
N3—C4—C3	117.70 (8)	O3—C11—H11B	109.3 (8)
C4—C5—C6	114.46 (9)	C10—C11—H11A	108.9 (9)
N2—C6—C1	104.95 (8)	C10—C11—H11B	110.1 (8)
N2—C6—C5	132.20 (9)	H11A—C11—H11B	110.5 (11)
C1—C6—C5	122.83 (9)	O3—C12—H12A	108.5 (9)
N1—C7—N2	114.65 (9)	O3—C12—H12B	111.0 (8)
N2—C8—C9	111.71 (8)	C13—C12—H12A	109.0 (9)
N4—C9—C8	110.25 (8)	C13—C12—H12B	108.8 (8)
N4—C10—C11	110.06 (8)	H12A—C12—H12B	108.8 (12)
O3—C11—C10	111.16 (8)	N4—C13—H13A	107.8 (8)
O3—C12—C13	110.70 (8)	N4—C13—H13B	107.1 (8)
N4—C13—C12	109.55 (8)	C12—C13—H13A	110.7 (8)
C1—C2—H2	120.6 (9)	C12—C13—H13B	110.8 (8)
C3—C2—H2	121.2 (9)	H13A—C13—H13B	110.9 (12)
C2—C3—H3	121.7 (9)

C12—O3—C11—C10	−62.09 (10)	C10—N4—C9—C8	−158.44 (8)
C11—O3—C12—C13	63.17 (10)	C13—N4—C9—C8	78.96 (9)
C7—N1—C1—C2	−179.13 (10)	C9—N4—C13—C12	178.13 (8)
C7—N1—C1—C6	−0.28 (11)	N1—C1—C6—N2	0.49 (11)
C1—N1—C7—N2	−0.04 (13)	N1—C1—C6—C5	−177.83 (9)
C7—N2—C6—C5	177.61 (10)	N1—C1—C2—C3	178.18 (10)
C8—N2—C6—C1	−174.79 (9)	C2—C1—C6—C5	1.13 (15)
C8—N2—C6—C5	3.31 (17)	C6—C1—C2—C3	−0.56 (14)
C7—N2—C8—C9	108.94 (10)	C2—C1—C6—N2	179.45 (9)
C6—N2—C8—C9	−77.76 (12)	C1—C2—C3—C4	−0.39 (14)
C7—N2—C6—C1	−0.49 (10)	C2—C3—C4—C5	0.90 (15)
C8—N2—C7—N1	174.93 (9)	C2—C3—C4—N3	−178.46 (9)
C6—N2—C7—N1	0.35 (12)	C3—C4—C5—C6	−0.38 (14)
O1—N3—C4—C5	174.53 (10)	N3—C4—C5—C6	178.99 (8)
O2—N3—C4—C5	−6.43 (14)	C4—C5—C6—N2	−178.45 (10)
O1—N3—C4—C3	−6.06 (14)	C4—C5—C6—C1	−0.64 (14)
O2—N3—C4—C3	172.98 (9)	N2—C8—C9—N4	−165.05 (8)
C13—N4—C10—C11	−53.61 (10)	N4—C10—C11—O3	57.91 (10)
C9—N4—C10—C11	−177.59 (8)	O3—C12—C13—N4	−59.99 (11)
C10—N4—C13—C12	54.58 (10)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z; (v) x, y−1, z; (vi) −x+1, −y, −z+1; (vii) x, y+1, z−1; (viii) −x+2, −y+1, −z+1; (ix) x, y, z+1; (x) x, y−1, z+1; (xi) −x+2, −y+1, −z; (xii) x, y+1, z; (xiii) x, y, z−1; (xiv) x+1, y, z; (xv) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···Cl1	0.903 (14)	2.151 (14)	3.0517 (9)	176.0 (12)
C3—H3···O3^x	0.963 (16)	2.399 (16)	3.2840 (13)	152.6 (13)
C5—H5···Cl1ⁱ	0.937 (15)	2.760 (15)	3.6627 (10)	162.1 (12)
C7—H7···O1^xii	0.961 (15)	2.334 (15)	3.2845 (13)	169.9 (12)
C9—H9A···Cl1ⁱ	0.963 (14)	2.652 (14)	3.5562 (10)	156.6 (11)
C12—H12B···O2ⁱ	0.979 (14)	2.519 (14)	3.3412 (14)	141.5 (11)
C13—H13A···O2^xii	0.966 (14)	2.425 (14)	3.2462 (13)	142.6 (11)

Symmetry codes: (i) −x+1, −y+1, −z; (x) x, y−1, z+1; (xii) x, y+1, z.

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