(S)-4-[2-(3-Cyano­benzamido)-3-hydroxy­prop­yl]phenyl 3-cyano­benzoate

Non-planar mol­ecules of the title compound, C₂₅H₁₉N₄O₃, are linked by inter­molecular N—H...O, O—H...N and C—H...O hydrogen bonds to form a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.038
• wR factor = 0.079
• Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.97 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C17     ..       5.29 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C23    -   C25    ...       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N1  -C1  -C2  -C3     11.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            N1  -C1  -C2  -C7      7.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         55
            C24 -C23 -C25 -N3      1.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         56
            C22 -C23 -C25 -N3     17.00  0.00   1.555   1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.37
           From the CIF: _reflns_number_total               2438
           Count of symmetry unique reflns         2472
           Completeness (_total/calc)             98.62%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; 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: SHELXL97.

(S)-4-[2-(3-Cyanobenzamido)-3-hydroxypropyl]phenyl 3-cyanobenzoate

Crystal data

C25H19N3O4	F(000) = 888
Mr = 425.43	Dx = 1.312 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 681 reflections
a = 32.665 (9) Å	θ = 2.5–17.0°
b = 4.778 (1) Å	µ = 0.09 mm^−1
c = 15.015 (4) Å	T = 299 K
β = 113.19 (2)°	Long needle, colourless
V = 2154.1 (9) Å^3	0.50 × 0.08 × 0.02 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2438 independent reflections
Radiation source: fine-focus sealed tube	1261 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 4.2°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004)	h = −40→40
Tmin = 0.974, Tmax = 0.998	k = −4→5
7760 measured reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H-atom parameters constrained
S = 0.88	w = 1/[σ^2(Fo^2) + (0.0294P)^2] where P = (Fo^2 + 2Fc^2)/3
2438 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.15 e Å^−3
1 restraint	Δρmin = −0.14 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
O1	0.14379 (8)	0.3447 (7)	0.35007 (19)	0.0812 (9)
O3	0.43176 (8)	0.1263 (6)	0.48333 (17)	0.0761 (8)
H3O	0.4404	0.0802	0.4411	0.091*
O4	0.34124 (8)	0.8483 (5)	0.25373 (16)	0.0581 (7)
N1	−0.03983 (12)	0.5075 (12)	0.3194 (3)	0.1269 (19)
O2	0.16193 (7)	0.6439 (5)	0.25713 (15)	0.0582 (7)
N2	0.36583 (8)	0.4191 (6)	0.31506 (18)	0.0426 (7)
H2N	0.3705	0.2502	0.3017	0.051*
N3	0.40966 (14)	−0.1541 (10)	0.0017 (3)	0.1072 (14)
C1	−0.01539 (14)	0.5824 (12)	0.2880 (3)	0.0941 (17)
C2	0.01557 (12)	0.6760 (11)	0.2481 (3)	0.0671 (12)
C3	0.00342 (14)	0.8705 (11)	0.1752 (3)	0.0822 (13)
H3	−0.0253	0.9428	0.1506	0.099*
C4	0.03374 (15)	0.9589 (10)	0.1386 (3)	0.0833 (14)
H4	0.0256	1.0913	0.0892	0.100*
C5	0.07626 (13)	0.8506 (9)	0.1752 (3)	0.0651 (11)
H5	0.0969	0.9126	0.1511	0.078*
C6	0.08848 (11)	0.6506 (9)	0.2474 (2)	0.0516 (9)
C7	0.05790 (12)	0.5635 (9)	0.2847 (2)	0.0623 (12)
H7	0.0659	0.4308	0.3340	0.075*
C8	0.13328 (12)	0.5251 (9)	0.2908 (3)	0.0527 (10)
C9	0.20717 (11)	0.5657 (8)	0.3051 (2)	0.0489 (10)
C10	0.23322 (12)	0.7125 (8)	0.3859 (2)	0.0537 (10)
H10	0.2211	0.8555	0.4099	0.064*
C11	0.27759 (12)	0.6449 (8)	0.4311 (2)	0.0492 (9)
H11	0.2957	0.7468	0.4851	0.059*
C12	0.29584 (11)	0.4273 (8)	0.3978 (2)	0.0436 (9)
C13	0.26869 (12)	0.2875 (8)	0.3151 (2)	0.0546 (10)
H13	0.2805	0.1453	0.2902	0.065*
C14	0.22412 (12)	0.3562 (8)	0.2688 (2)	0.0543 (10)
H14	0.2060	0.2599	0.2135	0.065*
C15	0.34382 (10)	0.3459 (8)	0.4516 (2)	0.0509 (9)
H15A	0.3465	0.1452	0.4460	0.061*
H15B	0.3524	0.3888	0.5198	0.061*
C16	0.37631 (10)	0.4924 (7)	0.4158 (2)	0.0440 (9)
H16	0.3726	0.6950	0.4194	0.053*
C17	0.42446 (12)	0.4191 (8)	0.4790 (3)	0.0584 (10)
H17A	0.4441	0.5091	0.4532	0.070*
H17B	0.4317	0.4903	0.5440	0.070*
C18	0.34936 (10)	0.6008 (8)	0.2429 (2)	0.0409 (9)
C19	0.34024 (10)	0.4933 (7)	0.1429 (2)	0.0386 (9)
C20	0.30544 (11)	0.6079 (8)	0.0655 (2)	0.0504 (9)
H20	0.2880	0.7466	0.0765	0.061*
C21	0.29606 (13)	0.5203 (9)	−0.0277 (3)	0.0661 (12)
H21	0.2719	0.5944	−0.0791	0.079*
C22	0.32278 (14)	0.3223 (10)	−0.0442 (3)	0.0672 (12)
H22	0.3170	0.2636	−0.1071	0.081*
C23	0.35812 (13)	0.2109 (8)	0.0323 (3)	0.0550 (10)
C24	0.36655 (11)	0.2921 (7)	0.1258 (2)	0.0433 (9)
H24	0.3899	0.2116	0.1773	0.052*
C25	0.38668 (16)	0.0074 (10)	0.0147 (3)	0.0730 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0588 (16)	0.102 (2)	0.085 (2)	0.0145 (18)	0.0308 (15)	0.047 (2)
O3	0.0811 (19)	0.069 (2)	0.0804 (19)	0.0116 (18)	0.0346 (15)	0.0063 (18)
O4	0.0836 (17)	0.0349 (17)	0.0591 (16)	0.0058 (15)	0.0318 (13)	0.0008 (14)
N1	0.068 (2)	0.197 (6)	0.128 (3)	0.028 (3)	0.052 (2)	0.039 (3)
O2	0.0536 (15)	0.076 (2)	0.0492 (14)	0.0110 (15)	0.0244 (12)	0.0145 (15)
N2	0.0594 (17)	0.0335 (18)	0.0381 (16)	0.0072 (15)	0.0224 (14)	0.0004 (16)
N3	0.148 (4)	0.084 (3)	0.129 (3)	0.013 (3)	0.097 (3)	−0.014 (3)
C1	0.054 (3)	0.139 (5)	0.087 (3)	0.023 (3)	0.026 (2)	0.008 (3)
C2	0.048 (2)	0.091 (4)	0.059 (2)	0.011 (3)	0.019 (2)	−0.001 (3)
C3	0.060 (3)	0.096 (4)	0.076 (3)	0.016 (3)	0.012 (3)	0.005 (3)
C4	0.072 (3)	0.097 (4)	0.065 (3)	0.007 (3)	0.009 (2)	0.021 (3)
C5	0.060 (3)	0.080 (3)	0.051 (2)	−0.001 (3)	0.017 (2)	0.003 (3)
C6	0.048 (2)	0.065 (3)	0.040 (2)	0.002 (2)	0.0154 (18)	−0.002 (2)
C7	0.059 (2)	0.077 (3)	0.050 (2)	0.005 (2)	0.021 (2)	0.000 (2)
C8	0.057 (3)	0.061 (3)	0.042 (2)	0.005 (2)	0.021 (2)	0.005 (2)
C9	0.048 (2)	0.065 (3)	0.040 (2)	0.011 (2)	0.0240 (19)	0.010 (2)
C10	0.066 (3)	0.059 (3)	0.045 (2)	0.005 (2)	0.032 (2)	−0.005 (2)
C11	0.058 (2)	0.053 (3)	0.042 (2)	−0.007 (2)	0.0257 (19)	−0.005 (2)
C12	0.057 (2)	0.046 (2)	0.0350 (19)	−0.001 (2)	0.0253 (18)	0.006 (2)
C13	0.063 (2)	0.057 (3)	0.051 (2)	0.006 (2)	0.031 (2)	−0.005 (2)
C14	0.058 (2)	0.059 (3)	0.044 (2)	0.001 (2)	0.0178 (19)	−0.009 (2)
C15	0.060 (2)	0.057 (2)	0.0401 (19)	0.005 (2)	0.0245 (18)	0.004 (2)
C16	0.054 (2)	0.038 (2)	0.041 (2)	−0.0022 (19)	0.0202 (18)	−0.0075 (18)
C17	0.061 (3)	0.048 (3)	0.062 (2)	0.000 (2)	0.020 (2)	0.000 (2)
C18	0.044 (2)	0.034 (2)	0.048 (2)	0.0003 (19)	0.0215 (17)	−0.002 (2)
C19	0.042 (2)	0.035 (2)	0.041 (2)	−0.0071 (18)	0.0192 (18)	0.0024 (18)
C20	0.052 (2)	0.053 (3)	0.049 (2)	0.005 (2)	0.0228 (19)	0.005 (2)
C21	0.063 (3)	0.082 (3)	0.047 (2)	−0.008 (3)	0.014 (2)	0.011 (2)
C22	0.086 (3)	0.074 (3)	0.046 (2)	−0.022 (3)	0.031 (2)	−0.010 (3)
C23	0.070 (3)	0.054 (3)	0.056 (2)	−0.005 (2)	0.041 (2)	−0.005 (2)
C24	0.053 (2)	0.042 (2)	0.0398 (19)	−0.004 (2)	0.0235 (17)	−0.0013 (18)
C25	0.105 (4)	0.066 (3)	0.068 (3)	−0.008 (3)	0.056 (3)	−0.006 (3)

Geometric parameters (Å, º)

O1—C8	1.188 (4)	C11—C12	1.387 (4)
O3—C17	1.416 (5)	C11—H11	0.9300
O3—H3O	0.8200	C12—C13	1.381 (4)
O4—C18	1.237 (4)	C12—C15	1.505 (4)
N1—C1	1.133 (5)	C13—C14	1.383 (4)
O2—C8	1.351 (4)	C13—H13	0.9300
O2—C9	1.415 (4)	C14—H14	0.9300
N2—C18	1.326 (4)	C15—C16	1.535 (4)
N2—C16	1.456 (3)	C15—H15A	0.9700
N2—H2N	0.8600	C15—H15B	0.9700
N3—C25	1.146 (5)	C16—C17	1.524 (4)
C1—C2	1.435 (6)	C16—H16	0.9800
C2—C3	1.369 (6)	C17—H17A	0.9700
C2—C7	1.380 (5)	C17—H17B	0.9700
C3—C4	1.375 (5)	C18—C19	1.502 (4)
C3—H3	0.9300	C19—C20	1.379 (4)
C4—C5	1.378 (5)	C19—C24	1.379 (4)
C4—H4	0.9300	C20—C21	1.374 (4)
C5—C6	1.381 (5)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.375 (5)
C6—C7	1.388 (4)	C21—H21	0.9300
C6—C8	1.475 (5)	C22—C23	1.375 (5)
C7—H7	0.9300	C22—H22	0.9300
C9—C14	1.358 (4)	C23—C24	1.376 (4)
C9—C10	1.370 (4)	C23—C25	1.442 (6)
C10—C11	1.375 (4)	C24—H24	0.9300
C10—H10	0.9300
C17—O3—H3O	109.5	C9—C14—H14	120.4
C8—O2—C9	115.9 (3)	C13—C14—H14	120.4
C18—N2—C16	123.0 (3)	C12—C15—C16	114.3 (3)
C18—N2—H2N	118.5	C12—C15—H15A	108.7
C16—N2—H2N	118.5	C16—C15—H15A	108.7
N1—C1—C2	179.7 (6)	C12—C15—H15B	108.7
C3—C2—C7	120.8 (4)	C16—C15—H15B	108.7
C3—C2—C1	121.0 (4)	H15A—C15—H15B	107.6
C7—C2—C1	118.2 (4)	N2—C16—C17	110.8 (3)
C2—C3—C4	120.0 (4)	N2—C16—C15	110.0 (3)
C2—C3—H3	120.0	C17—C16—C15	111.3 (3)
C4—C3—H3	120.0	N2—C16—H16	108.2
C3—C4—C5	119.8 (4)	C17—C16—H16	108.2
C3—C4—H4	120.1	C15—C16—H16	108.2
C5—C4—H4	120.1	O3—C17—C16	111.7 (3)
C4—C5—C6	120.5 (4)	O3—C17—H17A	109.3
C4—C5—H5	119.8	C16—C17—H17A	109.3
C6—C5—H5	119.8	O3—C17—H17B	109.3
C5—C6—C7	119.5 (3)	C16—C17—H17B	109.3
C5—C6—C8	123.9 (4)	H17A—C17—H17B	107.9
C7—C6—C8	116.5 (4)	O4—C18—N2	123.9 (3)
C2—C7—C6	119.3 (4)	O4—C18—C19	119.3 (3)
C2—C7—H7	120.3	N2—C18—C19	116.8 (3)
C6—C7—H7	120.3	C20—C19—C24	119.2 (3)
O1—C8—O2	123.1 (3)	C20—C19—C18	118.7 (3)
O1—C8—C6	124.7 (4)	C24—C19—C18	122.1 (3)
O2—C8—C6	112.1 (4)	C21—C20—C19	121.1 (3)
C14—C9—C10	121.6 (3)	C21—C20—H20	119.5
C14—C9—O2	120.0 (3)	C19—C20—H20	119.5
C10—C9—O2	118.4 (3)	C20—C21—C22	119.4 (4)
C9—C10—C11	118.9 (3)	C20—C21—H21	120.3
C9—C10—H10	120.5	C22—C21—H21	120.3
C11—C10—H10	120.5	C21—C22—C23	120.0 (4)
C10—C11—C12	121.2 (3)	C21—C22—H22	120.0
C10—C11—H11	119.4	C23—C22—H22	120.0
C12—C11—H11	119.4	C24—C23—C22	120.5 (4)
C13—C12—C11	118.2 (3)	C24—C23—C25	119.6 (4)
C13—C12—C15	121.5 (3)	C22—C23—C25	119.9 (4)
C11—C12—C15	120.3 (3)	C23—C24—C19	119.8 (3)
C12—C13—C14	120.9 (3)	C23—C24—H24	120.1
C12—C13—H13	119.6	C19—C24—H24	120.1
C14—C13—H13	119.6	N3—C25—C23	179.3 (6)
C9—C14—C13	119.2 (3)
N1—C1—C2—C3	114 (100)	O2—C9—C14—C13	178.3 (3)
N1—C1—C2—C7	−66 (100)	C12—C13—C14—C9	0.6 (5)
C7—C2—C3—C4	−0.9 (6)	C13—C12—C15—C16	88.4 (4)
C1—C2—C3—C4	179.5 (5)	C11—C12—C15—C16	−92.4 (3)
C2—C3—C4—C5	0.2 (6)	C18—N2—C16—C17	−125.3 (3)
C3—C4—C5—C6	1.0 (6)	C18—N2—C16—C15	111.2 (3)
C4—C5—C6—C7	−1.5 (6)	C12—C15—C16—N2	−61.7 (4)
C4—C5—C6—C8	−179.7 (4)	C12—C15—C16—C17	175.1 (3)
C3—C2—C7—C6	0.4 (6)	N2—C16—C17—O3	−65.9 (4)
C1—C2—C7—C6	−180.0 (4)	C15—C16—C17—O3	56.9 (4)
C5—C6—C7—C2	0.8 (5)	C16—N2—C18—O4	−0.1 (5)
C8—C6—C7—C2	179.2 (3)	C16—N2—C18—C19	−180.0 (2)
C9—O2—C8—O1	−7.5 (5)	O4—C18—C19—C20	−31.5 (4)
C9—O2—C8—C6	171.0 (3)	N2—C18—C19—C20	148.4 (3)
C5—C6—C8—O1	−176.7 (4)	O4—C18—C19—C24	146.0 (3)
C7—C6—C8—O1	5.0 (5)	N2—C18—C19—C24	−34.2 (4)
C5—C6—C8—O2	4.8 (5)	C24—C19—C20—C21	1.5 (5)
C7—C6—C8—O2	−173.4 (3)	C18—C19—C20—C21	179.0 (3)
C8—O2—C9—C14	95.5 (3)	C19—C20—C21—C22	−2.3 (5)
C8—O2—C9—C10	−86.8 (4)	C20—C21—C22—C23	0.9 (5)
C14—C9—C10—C11	0.0 (5)	C21—C22—C23—C24	1.3 (5)
O2—C9—C10—C11	−177.7 (3)	C21—C22—C23—C25	−178.7 (3)
C9—C10—C11—C12	−1.7 (5)	C22—C23—C24—C19	−2.1 (5)
C10—C11—C12—C13	2.8 (5)	C25—C23—C24—C19	177.9 (3)
C10—C11—C12—C15	−176.4 (3)	C20—C19—C24—C23	0.7 (4)
C11—C12—C13—C14	−2.2 (5)	C18—C19—C24—C23	−176.7 (3)
C15—C12—C13—C14	177.0 (3)	C24—C23—C25—N3	−7 (38)
C10—C9—C14—C13	0.6 (5)	C22—C23—C25—N3	173 (100)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4^i	0.86	2.14	2.889 (4)	145
O3—H3O···N1^ii	0.82	2.19	3.007 (5)	173
C11—H11···O1^iii	0.93	2.53	3.414 (4)	159

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