Crystal structure of 4-(3,4-di­cyano­phen­oxy)-N-[3-(di­methyl­amino)­prop­yl]benzamide mono­hydrate: a phen­oxy­phthalo­nitrile derivative

In the title compound, C₂₀H₂₀N₄O₂·H₂O, the planes of the phen­oxy and phthalo­nitrile rings are oriented at a dihedral angle of 60.39 (5)°. The 3-(di­­methyl­amino)­propyl chain has an extended conformation and is cis with respect to the phthalo­nitrile ring. In the crystal, O-H...O, O-H...N and N-H...O hydrogen bonds link the mol­ecules to form slabs parallel to (100). There are also C-H...O and C-H...N hydrogen bonds and C-H...[pi] inter­actions present within the slabs. The slabs are linked by a pair of inversion-related C-H...N hydrogen bonds, involving phthalo­nitrile rings, forming a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.134
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.385 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          6 Report

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

4-(3,4-Dicyanophenoxy)-N-[3-(dimethylamino)propyl]benzamide monohydrate

Crystal data

C20H20N4O2·H2O	F(000) = 776
Mr = 366.42	Dx = 1.290 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3102 reflections
a = 12.9004 (4) Å	θ = 2.4–27.6°
b = 10.5012 (3) Å	µ = 0.09 mm^−1
c = 14.1343 (4) Å	T = 100 K
β = 99.819 (5)°	Block, colourless
V = 1886.72 (10) Å^3	0.41 × 0.21 × 0.12 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer	4167 independent reflections
Radiation source: fine-focus sealed tube	3181 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 8.3333 pixels mm^-1	θmax = 27.1°, θmin = 1.6°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −13→8
Tmin = 0.964, Tmax = 0.989	l = −18→8
11419 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.8262P] where P = (Fo^2 + 2Fc^2)/3
4167 reflections	(Δ/σ)max < 0.001
258 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.67288 (10)	0.57054 (11)	0.44706 (9)	0.0266 (3)
O2	0.89189 (10)	0.80540 (12)	0.12674 (9)	0.0268 (3)
O3	0.03612 (13)	0.61391 (15)	0.10156 (11)	0.0390 (4)
H31	0.069 (2)	0.647 (3)	0.050 (2)	0.067 (8)*
H32	−0.008 (2)	0.676 (3)	0.107 (2)	0.069 (9)*
N1	0.44298 (14)	0.98877 (15)	0.59877 (12)	0.0309 (4)
N2	0.41361 (14)	0.74623 (16)	0.79739 (12)	0.0324 (4)
N3	0.92472 (12)	0.97057 (14)	0.22694 (11)	0.0218 (3)
H3	0.9178 (18)	1.006 (2)	0.2828 (17)	0.041 (6)*
N4	0.84238 (12)	1.30422 (14)	0.03388 (11)	0.0256 (4)
C1	0.62353 (14)	0.61497 (16)	0.51863 (12)	0.0209 (4)
C2	0.57723 (14)	0.73408 (16)	0.51653 (12)	0.0207 (4)
H2	0.5815	0.7908	0.4668	0.025*
C3	0.52459 (13)	0.76621 (16)	0.59012 (12)	0.0202 (4)
C4	0.51636 (13)	0.68108 (16)	0.66442 (12)	0.0204 (4)
C5	0.56370 (15)	0.56311 (17)	0.66438 (13)	0.0244 (4)
H5	0.5594	0.5056	0.7136	0.029*
C6	0.61708 (14)	0.53065 (17)	0.59187 (13)	0.0242 (4)
H6	0.6491	0.4512	0.5922	0.029*
C7	0.47916 (15)	0.89059 (17)	0.59306 (13)	0.0233 (4)
C8	0.45955 (14)	0.71679 (17)	0.73886 (13)	0.0234 (4)
C9	0.71794 (13)	0.65280 (16)	0.38897 (12)	0.0207 (4)
C10	0.70886 (13)	0.61852 (16)	0.29416 (12)	0.0212 (4)
H10	0.6684	0.5486	0.2704	0.025*
C11	0.76049 (13)	0.68930 (16)	0.23528 (12)	0.0208 (4)
H11	0.7549	0.6665	0.1710	0.025*
C12	0.82069 (13)	0.79391 (16)	0.26930 (12)	0.0188 (4)
C13	0.82780 (14)	0.82712 (17)	0.36507 (12)	0.0217 (4)
H13	0.8671	0.8979	0.3889	0.026*
C14	0.77737 (14)	0.75652 (17)	0.42502 (12)	0.0232 (4)
H14	0.7832	0.7784	0.4895	0.028*
C15	0.88129 (13)	0.85836 (17)	0.20237 (12)	0.0196 (4)
C16	0.99496 (14)	1.02932 (18)	0.16930 (13)	0.0253 (4)
H16A	1.0372	0.9633	0.1465	0.030*
H16B	1.0424	1.0863	0.2098	0.030*
C17	0.93865 (15)	1.10365 (17)	0.08368 (13)	0.0246 (4)
H17A	0.9893	1.1300	0.0441	0.029*
H17B	0.8875	1.0487	0.0452	0.029*
C18	0.88309 (14)	1.22012 (17)	0.11356 (13)	0.0246 (4)
H18A	0.8252	1.1927	0.1444	0.030*
H18B	0.9318	1.2676	0.1605	0.030*
C19	0.80249 (17)	1.42049 (19)	0.07052 (16)	0.0351 (5)
H19A	0.8586	1.4633	0.1118	0.053*
H19B	0.7477	1.3998	0.1062	0.053*
H19C	0.7748	1.4752	0.0178	0.053*
C20	0.75924 (17)	1.2439 (2)	−0.03341 (16)	0.0389 (5)
H20A	0.7852	1.1663	−0.0567	0.058*
H20B	0.7366	1.3003	−0.0863	0.058*
H20C	0.7009	1.2251	−0.0016	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0395 (8)	0.0162 (6)	0.0278 (7)	0.0019 (5)	0.0165 (6)	0.0011 (5)
O2	0.0318 (7)	0.0291 (7)	0.0212 (6)	−0.0018 (6)	0.0090 (5)	−0.0043 (5)
O3	0.0504 (10)	0.0340 (9)	0.0376 (9)	0.0149 (7)	0.0218 (7)	0.0141 (7)
N1	0.0405 (10)	0.0237 (9)	0.0304 (9)	0.0052 (7)	0.0115 (7)	0.0025 (7)
N2	0.0398 (10)	0.0268 (9)	0.0338 (9)	0.0026 (7)	0.0155 (8)	−0.0002 (7)
N3	0.0260 (8)	0.0203 (8)	0.0198 (8)	−0.0014 (6)	0.0058 (6)	0.0015 (6)
N4	0.0267 (8)	0.0210 (8)	0.0297 (8)	−0.0017 (6)	0.0062 (7)	0.0022 (6)
C1	0.0231 (9)	0.0180 (9)	0.0222 (9)	−0.0005 (7)	0.0052 (7)	−0.0022 (7)
C2	0.0246 (9)	0.0179 (9)	0.0197 (8)	−0.0005 (7)	0.0043 (7)	0.0033 (7)
C3	0.0206 (8)	0.0168 (8)	0.0225 (9)	−0.0002 (7)	0.0020 (7)	0.0002 (7)
C4	0.0209 (8)	0.0193 (9)	0.0217 (8)	−0.0024 (7)	0.0056 (7)	−0.0008 (7)
C5	0.0313 (10)	0.0191 (9)	0.0240 (9)	−0.0010 (8)	0.0083 (7)	0.0051 (7)
C6	0.0295 (10)	0.0164 (9)	0.0280 (9)	0.0031 (7)	0.0087 (8)	0.0031 (7)
C7	0.0281 (9)	0.0204 (9)	0.0221 (9)	−0.0020 (7)	0.0060 (7)	0.0011 (7)
C8	0.0291 (10)	0.0164 (9)	0.0256 (9)	−0.0009 (7)	0.0069 (8)	0.0025 (7)
C9	0.0230 (9)	0.0167 (8)	0.0232 (9)	0.0048 (7)	0.0067 (7)	0.0041 (7)
C10	0.0202 (9)	0.0178 (9)	0.0258 (9)	0.0007 (7)	0.0040 (7)	−0.0019 (7)
C11	0.0222 (9)	0.0216 (9)	0.0178 (8)	0.0022 (7)	0.0014 (7)	−0.0019 (7)
C12	0.0191 (8)	0.0178 (8)	0.0195 (8)	0.0056 (7)	0.0030 (6)	0.0016 (6)
C13	0.0260 (9)	0.0182 (9)	0.0210 (8)	−0.0005 (7)	0.0039 (7)	−0.0021 (7)
C14	0.0298 (10)	0.0229 (9)	0.0169 (8)	0.0007 (7)	0.0040 (7)	−0.0005 (7)
C15	0.0190 (8)	0.0206 (9)	0.0185 (8)	0.0040 (7)	0.0015 (6)	0.0016 (7)
C16	0.0213 (9)	0.0263 (10)	0.0289 (10)	−0.0025 (7)	0.0060 (7)	0.0037 (8)
C17	0.0261 (9)	0.0236 (10)	0.0251 (9)	−0.0018 (7)	0.0074 (7)	0.0022 (7)
C18	0.0240 (9)	0.0244 (10)	0.0259 (9)	−0.0022 (7)	0.0055 (7)	0.0009 (7)
C19	0.0359 (11)	0.0263 (10)	0.0452 (12)	0.0042 (9)	0.0128 (9)	0.0023 (9)
C20	0.0384 (12)	0.0285 (11)	0.0444 (13)	−0.0020 (9)	−0.0083 (10)	0.0059 (9)

Geometric parameters (Å, º)

O1—C1	1.366 (2)	C11—C10	1.370 (2)
O1—C9	1.386 (2)	C11—H11	0.9300
O2—C15	1.233 (2)	C12—C11	1.383 (2)
O3—H31	0.96 (3)	C12—C13	1.386 (2)
O3—H32	0.87 (3)	C13—H13	0.9300
N1—C7	1.140 (2)	C14—C9	1.379 (2)
N3—C16	1.455 (2)	C14—C13	1.371 (2)
N3—H3	0.89 (2)	C14—H14	0.9300
N4—C18	1.457 (2)	C15—N3	1.325 (2)
N4—C19	1.454 (2)	C15—C12	1.489 (2)
N4—C20	1.452 (2)	C16—C17	1.517 (2)
C1—C2	1.384 (2)	C16—H16A	0.9700
C1—C6	1.376 (2)	C16—H16B	0.9700
C2—C3	1.378 (2)	C17—C18	1.514 (3)
C2—H2	0.9300	C17—H17A	0.9700
C4—C3	1.397 (2)	C17—H17B	0.9700
C4—C5	1.381 (2)	C18—H18A	0.9700
C5—C6	1.372 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C3	1.435 (2)	C19—H19C	0.9600
C8—N2	1.140 (2)	C20—H20A	0.9600
C8—C4	1.431 (3)	C20—H20B	0.9600
C10—C9	1.373 (2)	C20—H20C	0.9600
C10—H10	0.9300
C1—O1—C9	121.43 (13)	C12—C13—H13	119.7
H31—O3—H32	99 (2)	C14—C13—C12	120.56 (16)
C15—N3—C16	120.40 (16)	C14—C13—H13	119.7
C15—N3—H3	120.2 (15)	C9—C14—H14	120.3
C16—N3—H3	119.0 (15)	C13—C14—C9	119.44 (16)
C19—N4—C18	109.66 (15)	C13—C14—H14	120.3
C20—N4—C18	111.73 (15)	O2—C15—N3	121.58 (16)
C20—N4—C19	109.46 (16)	O2—C15—C12	119.59 (16)
O1—C1—C2	123.13 (15)	N3—C15—C12	118.82 (15)
O1—C1—C6	115.67 (15)	N3—C16—C17	113.93 (15)
C6—C1—C2	121.10 (16)	N3—C16—H16A	108.8
C1—C2—H2	120.9	N3—C16—H16B	108.8
C3—C2—C1	118.13 (16)	C17—C16—H16A	108.8
C3—C2—H2	120.9	C17—C16—H16B	108.8
C2—C3—C4	121.43 (16)	H16A—C16—H16B	107.7
C2—C3—C7	120.07 (16)	C16—C17—H17A	109.2
C4—C3—C7	118.48 (16)	C16—C17—H17B	109.2
C5—C4—C3	118.90 (16)	C18—C17—C16	112.23 (15)
C5—C4—C8	121.15 (16)	C18—C17—H17A	109.2
C3—C4—C8	119.95 (16)	C18—C17—H17B	109.2
C4—C5—H5	119.9	H17A—C17—H17B	107.9
C6—C5—C4	120.11 (16)	N4—C18—C17	113.55 (15)
C6—C5—H5	119.9	N4—C18—H18A	108.9
C1—C6—H6	119.8	N4—C18—H18B	108.9
C5—C6—C1	120.32 (17)	C17—C18—H18A	108.9
C5—C6—H6	119.8	C17—C18—H18B	108.9
N1—C7—C3	177.56 (19)	H18A—C18—H18B	107.7
N2—C8—C4	179.2 (2)	N4—C19—H19A	109.5
C10—C9—O1	116.12 (16)	N4—C19—H19B	109.5
C10—C9—C14	121.15 (16)	N4—C19—H19C	109.5
C14—C9—O1	122.44 (15)	H19A—C19—H19B	109.5
C9—C10—H10	120.6	H19A—C19—H19C	109.5
C11—C10—C9	118.76 (16)	H19B—C19—H19C	109.5
C11—C10—H10	120.6	N4—C20—H20A	109.5
C10—C11—C12	121.46 (16)	N4—C20—H20B	109.5
C10—C11—H11	119.3	N4—C20—H20C	109.5
C12—C11—H11	119.3	H20A—C20—H20B	109.5
C11—C12—C13	118.63 (16)	H20A—C20—H20C	109.5
C11—C12—C15	117.69 (15)	H20B—C20—H20C	109.5
C13—C12—C15	123.50 (16)
C9—O1—C1—C2	26.8 (2)	C4—C5—C6—C1	−0.2 (3)
C9—O1—C1—C6	−156.73 (16)	C11—C10—C9—O1	−173.73 (15)
C1—O1—C9—C10	−142.73 (16)	C11—C10—C9—C14	0.2 (3)
C1—O1—C9—C14	43.4 (2)	C12—C11—C10—C9	−0.2 (3)
C15—N3—C16—C17	84.1 (2)	C13—C12—C11—C10	−0.3 (3)
C20—N4—C18—C17	65.6 (2)	C15—C12—C11—C10	174.86 (15)
C19—N4—C18—C17	−172.83 (16)	C11—C12—C13—C14	0.9 (3)
O1—C1—C2—C3	176.48 (16)	C15—C12—C13—C14	−173.97 (16)
C6—C1—C2—C3	0.2 (3)	C13—C14—C9—O1	173.93 (16)
O1—C1—C6—C5	−176.17 (16)	C13—C14—C9—C10	0.4 (3)
C2—C1—C6—C5	0.4 (3)	C9—C14—C13—C12	−0.9 (3)
C1—C2—C3—C4	−0.9 (3)	O2—C15—N3—C16	−5.9 (2)
C1—C2—C3—C7	177.39 (16)	C12—C15—N3—C16	172.51 (14)
C5—C4—C3—C2	1.1 (3)	O2—C15—C12—C11	−13.1 (2)
C5—C4—C3—C7	−177.27 (16)	O2—C15—C12—C13	161.88 (16)
C8—C4—C3—C2	−178.93 (16)	N3—C15—C12—C11	168.50 (15)
C8—C4—C3—C7	2.7 (2)	N3—C15—C12—C13	−16.6 (2)
C3—C4—C5—C6	−0.5 (3)	N3—C16—C17—C18	66.6 (2)
C8—C4—C5—C6	179.52 (17)	C16—C17—C18—N4	170.87 (15)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the phenoxy ring C9—C14.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3^i	0.89 (2)	1.99 (2)	2.825 (2)	155 (2)
O3—H31···N4^ii	0.97 (3)	1.85 (3)	2.808 (2)	168 (3)
O3—H32···O2^iii	0.88 (3)	1.93 (3)	2.803 (2)	176 (3)
C13—H13···O3^i	0.93	2.58	3.477 (2)	162
C14—H14···O2^iv	0.93	2.36	3.049 (2)	131
C16—H16B···Cg2^v	0.97	2.96	3.661 (2)	130
C2—H2···N1^vi	0.93	2.49	3.324 (2)	149

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