N-(4-Chloro­phen­yl)-N-(4,5-dihydro-1H-imidazol-2-yl)amine formamide solvate

In the title compound, C₉H₁₀ClN₃·HC(O)NH₂, the benzene and imidazole rings make a dihedral angle of 43.3 (1)°. In the crystal structure, mol­ecules are linked through weak inter­molecular N—H...O, N—H...N and C—H...N hydrogen bonds, forming a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.111
• Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X       H4B    ..  H9B     ..       2.00 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4B    ...          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: SADABS (Sheldrick, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(4-Chlorophenyl)-N-(4,5-dihydro-1H-imidazol-2-yl)amine formamide solvate

Crystal data

C9H10ClN3·CH3NO	F(000) = 504
Mr = 240.69	Dx = 1.472 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2 y b c	Cell parameters from 204 reflections
a = 8.5840 (5) Å	θ = 6–20°
b = 13.2740 (4) Å	µ = 0.34 mm^−1
c = 9.9080 (7) Å	T = 150 K
β = 105.789 (5)°	Block, colourless
V = 1086.4 (1) Å^3	0.32 × 0.09 × 0.07 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	2655 independent reflections
Radiation source: fine-focus sealed tube	2034 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 9 pixels mm^-1	θmax = 28.5°, θmin = 3.7°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −17→15
Tmin = 0.900, Tmax = 0.977	l = −13→13
15967 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0631P)^2 + 0.4854P] where P = (Fo^2 + 2Fc^2)/3
2655 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.57 e Å^−3

Special details

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 F² 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 F². The observed criterion of F² > σ(F²) 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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.03223 (5)	0.13649 (3)	1.04443 (5)	0.0247 (1)
N1	0.57929 (19)	0.26234 (11)	0.82569 (16)	0.0194 (4)
N2	0.78067 (19)	0.23704 (11)	0.71283 (16)	0.0202 (4)
N3	0.64043 (18)	0.10273 (12)	0.74120 (16)	0.0191 (4)
C1	0.4638 (2)	0.14431 (13)	0.96409 (18)	0.0191 (5)
C2	0.3325 (2)	0.11613 (14)	1.01374 (19)	0.0207 (5)
C3	0.1971 (2)	0.17666 (14)	0.98729 (17)	0.0183 (5)
C4	0.1892 (2)	0.26713 (14)	0.91624 (19)	0.0202 (5)
C5	0.3184 (2)	0.29344 (14)	0.86291 (19)	0.0203 (5)
C6	0.4535 (2)	0.23145 (13)	0.88365 (18)	0.0167 (5)
C7	0.6622 (2)	0.20147 (13)	0.76214 (17)	0.0161 (4)
C8	0.8552 (2)	0.15664 (14)	0.6514 (2)	0.0210 (5)
C9	0.7509 (2)	0.06467 (14)	0.6622 (2)	0.0234 (5)
O1	0.61744 (16)	0.46791 (9)	0.79428 (14)	0.0220 (4)
N4	0.87429 (17)	0.43528 (11)	0.79633 (17)	0.0201 (4)
C10	0.7618 (2)	0.49239 (13)	0.80339 (18)	0.0194 (5)
H1	0.55720	0.10520	0.98460	0.0230*
H1A	0.60460	0.32520	0.83170	0.0230*
H2	0.33650	0.05680	1.06440	0.0250*
H3	0.57220	0.06670	0.76950	0.0230*
H4	0.10010	0.30940	0.90430	0.0240*
H5	0.31400	0.35310	0.81290	0.0240*
H8A	0.96710	0.14630	0.70400	0.0250*
H8B	0.85070	0.17130	0.55450	0.0250*
H9A	0.69110	0.04120	0.56990	0.0280*
H9B	0.81710	0.01000	0.71200	0.0280*
H4A	0.85710	0.37170	0.78400	0.0240*
H4B	0.96920	0.45940	0.80380	0.0240*
H10	0.78690	0.56050	0.81680	0.0230*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0240 (2)	0.0244 (2)	0.0301 (2)	−0.0013 (2)	0.0149 (2)	0.0001 (2)
N1	0.0196 (7)	0.0125 (7)	0.0277 (8)	0.0005 (6)	0.0093 (6)	0.0009 (6)
N2	0.0183 (7)	0.0163 (7)	0.0286 (8)	−0.0007 (6)	0.0109 (6)	0.0001 (6)
N3	0.0184 (7)	0.0166 (7)	0.0255 (8)	−0.0009 (6)	0.0115 (6)	−0.0008 (6)
C1	0.0218 (8)	0.0151 (8)	0.0211 (8)	0.0061 (7)	0.0071 (7)	0.0013 (7)
C2	0.0289 (9)	0.0164 (8)	0.0200 (8)	0.0049 (7)	0.0119 (7)	0.0033 (6)
C3	0.0196 (8)	0.0196 (8)	0.0170 (8)	−0.0016 (7)	0.0071 (7)	−0.0025 (7)
C4	0.0166 (8)	0.0186 (8)	0.0254 (9)	0.0052 (7)	0.0055 (7)	0.0030 (7)
C5	0.0206 (9)	0.0170 (8)	0.0241 (9)	0.0030 (7)	0.0073 (7)	0.0041 (7)
C6	0.0175 (8)	0.0146 (8)	0.0177 (8)	−0.0002 (6)	0.0044 (6)	−0.0013 (6)
C7	0.0147 (7)	0.0150 (8)	0.0172 (8)	0.0000 (6)	0.0019 (6)	0.0025 (6)
C8	0.0192 (8)	0.0199 (9)	0.0264 (9)	−0.0010 (7)	0.0105 (7)	−0.0019 (7)
C9	0.0275 (9)	0.0170 (8)	0.0308 (9)	−0.0021 (7)	0.0164 (8)	−0.0033 (7)
O1	0.0185 (6)	0.0155 (6)	0.0334 (7)	0.0011 (5)	0.0094 (5)	0.0015 (5)
N4	0.0112 (7)	0.0126 (7)	0.0392 (9)	−0.0012 (5)	0.0117 (6)	−0.0035 (6)
C10	0.0204 (8)	0.0139 (8)	0.0251 (8)	−0.0009 (7)	0.0081 (7)	0.0006 (7)

Geometric parameters (Å, º)

Cl1—C3	1.7446 (18)	C2—C3	1.378 (3)
O1—C10	1.260 (2)	C3—C4	1.384 (3)
N1—C6	1.415 (2)	C4—C5	1.397 (3)
N1—C7	1.342 (2)	C5—C6	1.391 (3)
N2—C8	1.460 (2)	C8—C9	1.535 (3)
N2—C7	1.329 (2)	C1—H1	0.9300
N3—C7	1.332 (2)	C2—H2	0.9300
N3—C9	1.473 (2)	C4—H4	0.9300
N1—H1A	0.8600	C5—H5	0.9300
N3—H3	0.8600	C8—H8B	0.9700
N4—C10	1.245 (2)	C8—H8A	0.9700
N4—H4A	0.8600	C9—H9A	0.9700
N4—H4B	0.8600	C9—H9B	0.9700
C1—C2	1.398 (3)	C10—H10	0.9300
C1—C6	1.394 (2)
Cl1···C5^i	3.5550 (19)	C10···H1A	2.6500
Cl1···N2^ii	3.4966 (17)	H1···N3	2.7000
Cl1···N4^ii	3.2888 (17)	H1···C7	2.9000
Cl1···C8^ii	3.4423 (19)	H1···H2^iii	2.4400
Cl1···H9B^iii	3.1000	H1···H3	2.2300
Cl1···H4A^ii	3.1400	H1···C2^iii	3.0900
Cl1···H4B^ii	3.0500	H1A···O1	1.9400
Cl1···H5^i	3.0700	H1A···N4	2.8400
Cl1···H8B^ii	3.0100	H1A···C10	2.6500
O1···N3^iv	2.793 (2)	H1A···H4A	2.4200
O1···C1^iv	3.399 (2)	H1A···H5	2.4800
O1···N1	2.7759 (19)	H2···H3^iii	2.3000
O1···C2^v	3.355 (2)	H2···O1^i	2.8500
O1···H2^v	2.8500	H2···H1^iii	2.4400
O1···H3^iv	2.0500	H2···N3^iii	2.8300
O1···H1A	1.9400	H3···H1	2.2300
O1···H9A^i	2.6300	H3···C1	2.5700
N1···O1	2.7759 (19)	H3···C6	2.7800
N2···Cl1^vi	3.4966 (17)	H3···H2^iii	2.3000
N2···N4	2.809 (2)	H3···O1^vii	2.0500
N3···O1^vii	2.793 (2)	H3···C10^vii	2.9300
N3···C1	3.050 (2)	H4···N4^x	2.5600
N4···N2	2.809 (2)	H4···H4A^x	2.2600
N4···Cl1^vi	3.2888 (17)	H4···H4B^x	2.3700
N1···H8B^i	2.9100	H4A···H4^ix	2.2600
N1···H4A	2.9200	H4A···N1	2.9200
N2···H4A	1.9700	H4A···N2	1.9700
N3···H2^iii	2.8300	H4A···C7	2.7800
N3···H1	2.7000	H4A···H1A	2.4200
N4···H1A	2.8400	H4A···Cl1^vi	3.1400
N4···H9B^viii	2.8500	H4B···Cl1^vi	3.0500
N4···H4^ix	2.5600	H4B···H4^ix	2.3700
C1···N3	3.050 (2)	H4B···C8^viii	2.9900
C1···C10^vii	3.471 (2)	H4B···C9^viii	2.7200
C1···O1^vii	3.399 (2)	H4B···H8A^viii	2.5500
C2···O1^i	3.355 (2)	H4B···H9B^viii	2.0000
C2···C10^vii	3.441 (3)	H5···H1A	2.4800
C5···Cl1^v	3.5550 (19)	H5···Cl1^v	3.0700
C8···Cl1^vi	3.4423 (19)	H5···C9^iv	2.8900
C10···C2^iv	3.441 (3)	H5···H9B^iv	2.3500
C10···C1^iv	3.471 (2)	H5···C2^v	3.0400
C1···H3	2.5700	H8A···H4B^xi	2.5500
C2···H1^iii	3.0900	H8A···C3^ix	2.9900
C2···H5^i	3.0400	H8A···C4^ix	2.9100
C3···H8A^x	2.9900	H8A···H10^xi	2.4600
C4···H8A^x	2.9100	H8B···N1^v	2.9100
C6···H3	2.7800	H8B···Cl1^vi	3.0100
C7···H4A	2.7800	H9A···O1^v	2.6300
C7···H1	2.9000	H9A···C10^v	2.9000
C8···H4B^xi	2.9900	H9B···Cl1^iii	3.1000
C9···H5^vii	2.8900	H9B···N4^xi	2.8500
C9···H4B^xi	2.7200	H9B···H4B^xi	2.0000
C10···H3^iv	2.9300	H9B···H5^vii	2.3500
C10···H9A^i	2.9000	H10···H8A^viii	2.4600
C6—N1—C7	125.24 (15)	N2—C8—C9	102.85 (14)
C7—N2—C8	111.07 (14)	N3—C9—C8	103.67 (15)
C7—N3—C9	109.68 (15)	C2—C1—H1	120.00
C6—N1—H1A	117.00	C6—C1—H1	120.00
C7—N1—H1A	117.00	C1—C2—H2	120.00
C7—N3—H3	125.00	C3—C2—H2	120.00
C9—N3—H3	125.00	C5—C4—H4	121.00
C10—N4—H4A	120.00	C3—C4—H4	121.00
C10—N4—H4B	120.00	C4—C5—H5	120.00
H4A—N4—H4B	120.00	C6—C5—H5	120.00
C2—C1—C6	119.44 (16)	N2—C8—H8A	111.00
C1—C2—C3	119.74 (17)	N2—C8—H8B	111.00
Cl1—C3—C4	119.89 (14)	C9—C8—H8A	111.00
C2—C3—C4	121.64 (17)	C9—C8—H8B	111.00
Cl1—C3—C2	118.47 (14)	H8A—C8—H8B	109.00
C3—C4—C5	118.38 (17)	C8—C9—H9A	111.00
C4—C5—C6	120.81 (17)	H9A—C9—H9B	109.00
C1—C6—C5	119.74 (16)	N3—C9—H9B	111.00
N1—C6—C5	117.80 (15)	C8—C9—H9B	111.00
N1—C6—C1	122.41 (16)	N3—C9—H9A	111.00
N1—C7—N2	121.02 (16)	O1—C10—N4	126.99 (17)
N2—C7—N3	112.41 (16)	O1—C10—H10	116.00
N1—C7—N3	126.57 (16)	N4—C10—H10	117.00
C7—N1—C6—C1	43.5 (3)	C2—C1—C6—C5	5.0 (3)
C7—N1—C6—C5	−139.01 (18)	C2—C1—C6—N1	−177.58 (16)
C6—N1—C7—N2	−178.83 (16)	C1—C2—C3—C4	−2.2 (3)
C6—N1—C7—N3	0.7 (3)	C1—C2—C3—Cl1	177.33 (14)
C8—N2—C7—N1	178.67 (16)	C2—C3—C4—C5	4.2 (3)
C8—N2—C7—N3	−0.9 (2)	Cl1—C3—C4—C5	−175.32 (14)
C7—N2—C8—C9	4.11 (19)	C3—C4—C5—C6	−1.6 (3)
C9—N3—C7—N2	−3.0 (2)	C4—C5—C6—C1	−3.0 (3)
C7—N3—C9—C8	5.26 (19)	C4—C5—C6—N1	179.47 (16)
C9—N3—C7—N1	177.49 (17)	N2—C8—C9—N3	−5.40 (18)
C6—C1—C2—C3	−2.5 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−1, −y+1/2, z+1/2; (iii) −x+1, −y, −z+2; (iv) −x+1, y+1/2, −z+3/2; (v) x, −y+1/2, z−1/2; (vi) x+1, −y+1/2, z−1/2; (vii) −x+1, y−1/2, −z+3/2; (viii) −x+2, y+1/2, −z+3/2; (ix) x+1, y, z; (x) x−1, y, z; (xi) −x+2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.94	2.7759 (19)	164
N3—H3···O1^vii	0.86	2.05	2.793 (2)	144
N4—H4A···N2	0.86	1.97	2.809 (2)	166
C4—H4···N4^x	0.93	2.56	3.457 (2)	162

Symmetry codes: (vii) −x+1, y−1/2, −z+3/2; (x) x−1, y, z.