Crystal structure and Hirshfeld surface analysis of diethyl 5-(2-cyano­phen­oxy)isophthalate

The title compound is non-planar, subtending a dihedral angle of 82.38 (4)° between the plane of hy­droxy isophthalate-based ester and that of the benzo­nitrile moiety. The mol­ecule is bent at the ether linkage, with a C_ar­yl—O—C_ar­yl bond angle of 116.74 (11)°. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds and other weak inter­actions forming a supra­molecular framework.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.110
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT934_ALERT_3_A Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..         12 Check
PLAT999_ALERT_1_A SHELXL LIST 6 Fo/Fc Unsuitable for FCF-Validation         ! Error

Alert level B
PLAT920_ALERT_1_B Theta(Max)  in CIF and FCF Differ by ...........      31.53 Degree
PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............     0.0077 Check
PLAT922_ALERT_1_B wR2 in the CIF and FCF Differ by ...............     0.0362 Check
PLAT923_ALERT_1_B S    Values in the CIF and FCF Differ by .......     -0.986 Check

Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.241 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.596          2 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        66% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ          10 Units
PLAT957_ALERT_1_G Calculated (ThMax) and Actual (FCF) Kmax Differ          12 Units
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ          19 Units
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

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

   8 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
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Diethyl 5-(2-cyanophenoxy)benzene-1,3-dicarboxylate

Crystal data

C19H17NO5	F(000) = 712.4237
Mr = 339.35	Dx = 1.345 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.3581 (5) Å	Cell parameters from 7552 reflections
b = 10.5306 (6) Å	θ = 3.2–28.2°
c = 17.0141 (10) Å	µ = 0.10 mm^−1
β = 91.967 (2)°	T = 100 K
V = 1675.69 (16) Å^3	Block, colourless
Z = 4	0.39 × 0.27 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer	3134 reflections with I ≥ 2σ(I)
φ and ω scans	Rint = 0.062
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 56.6°, θmin = 5.8°
Tmin = 0.611, Tmax = 0.746	h = −12→12
25974 measured reflections	k = −14→14
4149 independent reflections	l = −22→22

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Primary atom site location: iterative
R[F^2 > 2σ(F^2)] = 0.044	All H-atom parameters refined
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.035P)^2 + 0.7212P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
4149 reflections	Δρmax = 0.30 e Å^−3
294 parameters	Δρmin = −0.31 e Å^−3
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.22713 (11)	0.50496 (10)	0.53544 (6)	0.0229 (2)
O2	0.42747 (13)	0.38970 (12)	0.55579 (7)	0.0360 (3)
O3	0.06230 (11)	0.78631 (10)	0.73574 (6)	0.0213 (2)
O4	0.20643 (11)	0.84802 (11)	0.83720 (7)	0.0266 (3)
O5	0.64745 (11)	0.57614 (10)	0.80523 (6)	0.0232 (2)
N1	1.00269 (15)	0.58018 (13)	0.86616 (8)	0.0285 (3)
C1	0.1112 (2)	0.31216 (17)	0.48736 (11)	0.0312 (4)
H1a	0.026 (2)	0.3334 (18)	0.5175 (11)	0.036 (5)*
H1b	0.174 (2)	0.255 (2)	0.5194 (12)	0.044 (6)*
H1c	0.079 (2)	0.265 (2)	0.4393 (12)	0.045 (6)*
C2	0.19053 (19)	0.42986 (16)	0.46556 (9)	0.0255 (3)
H2a	0.279 (2)	0.4097 (17)	0.4384 (11)	0.030 (5)*
H2b	0.130 (2)	0.4875 (19)	0.4334 (11)	0.036 (5)*
C3	0.34773 (16)	0.47318 (14)	0.57513 (9)	0.0216 (3)
C4	0.37168 (16)	0.55112 (13)	0.64759 (9)	0.0187 (3)
C5	0.26900 (15)	0.63480 (14)	0.67416 (9)	0.0180 (3)
H5	0.1801 (18)	0.6472 (16)	0.6445 (10)	0.020 (4)*
C6	0.29409 (15)	0.70006 (13)	0.74438 (9)	0.0184 (3)
C7	0.18526 (15)	0.78627 (14)	0.77797 (9)	0.0193 (3)
C9	−0.05528 (16)	0.85475 (16)	0.77059 (10)	0.0238 (3)
H9a	−0.0642 (18)	0.8230 (17)	0.8257 (11)	0.026 (4)*
H9b	−0.0293 (18)	0.9469 (17)	0.7713 (10)	0.024 (4)*
C10	−0.18649 (17)	0.82704 (18)	0.72010 (11)	0.0282 (4)
H10a	−0.1759 (19)	0.8645 (18)	0.6671 (12)	0.033 (5)*
H10b	−0.202 (2)	0.735 (2)	0.7152 (11)	0.035 (5)*
H10c	−0.271 (2)	0.865 (2)	0.7460 (12)	0.044 (6)*
C11	0.42139 (16)	0.68242 (14)	0.78809 (9)	0.0198 (3)
H11	0.4401 (17)	0.7255 (16)	0.8374 (10)	0.021 (4)*
C12	0.52017 (15)	0.59670 (14)	0.76114 (9)	0.0193 (3)
C13	0.49852 (16)	0.53133 (14)	0.69155 (9)	0.0199 (3)
H13	0.5670 (17)	0.4739 (16)	0.6743 (9)	0.017 (4)*
C14	0.64157 (15)	0.49105 (14)	0.86643 (9)	0.0189 (3)
C15	0.51899 (17)	0.42882 (14)	0.88849 (9)	0.0216 (3)
H15	0.429 (2)	0.4474 (18)	0.8609 (11)	0.034 (5)*
C16	0.52654 (18)	0.34329 (15)	0.95050 (9)	0.0243 (3)
H16	0.4388 (18)	0.2977 (16)	0.9645 (10)	0.025 (4)*
C17	0.65468 (18)	0.31972 (15)	0.99145 (9)	0.0254 (3)
H17	0.659 (2)	0.2606 (18)	1.0337 (11)	0.034 (5)*
C18	0.77621 (17)	0.38328 (15)	0.97039 (9)	0.0229 (3)
H18	0.8631 (18)	0.3700 (16)	0.9991 (10)	0.023 (4)*
C19	0.77115 (15)	0.46874 (14)	0.90750 (9)	0.0194 (3)
C20	0.89888 (16)	0.53164 (15)	0.88389 (9)	0.0218 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0265 (6)	0.0223 (5)	0.0195 (5)	0.0021 (4)	−0.0050 (4)	−0.0020 (4)
O2	0.0327 (7)	0.0383 (7)	0.0368 (7)	0.0128 (6)	−0.0025 (5)	−0.0149 (6)
O3	0.0165 (5)	0.0264 (6)	0.0208 (5)	0.0056 (4)	−0.0010 (4)	−0.0018 (4)
O4	0.0237 (6)	0.0285 (6)	0.0274 (6)	−0.0002 (5)	−0.0019 (5)	−0.0096 (5)
O5	0.0154 (5)	0.0285 (6)	0.0252 (6)	−0.0019 (4)	−0.0048 (4)	0.0098 (5)
N1	0.0227 (7)	0.0311 (7)	0.0313 (8)	−0.0018 (6)	−0.0054 (6)	−0.0021 (6)
C1	0.0372 (10)	0.0299 (9)	0.0265 (9)	−0.0063 (8)	0.0035 (8)	−0.0051 (7)
C2	0.0340 (9)	0.0252 (8)	0.0172 (7)	−0.0020 (7)	−0.0022 (7)	−0.0022 (6)
C3	0.0219 (8)	0.0212 (7)	0.0218 (8)	0.0022 (6)	0.0006 (6)	0.0015 (6)
C4	0.0186 (7)	0.0183 (7)	0.0191 (7)	−0.0001 (6)	0.0005 (6)	0.0027 (6)
C5	0.0156 (7)	0.0185 (7)	0.0199 (7)	−0.0004 (6)	−0.0015 (6)	0.0039 (6)
C6	0.0173 (7)	0.0179 (7)	0.0200 (7)	−0.0004 (5)	0.0002 (6)	0.0036 (6)
C7	0.0174 (7)	0.0194 (7)	0.0212 (7)	−0.0007 (6)	−0.0006 (6)	0.0008 (6)
C9	0.0203 (8)	0.0280 (8)	0.0232 (8)	0.0073 (6)	0.0019 (6)	−0.0025 (7)
C10	0.0185 (8)	0.0373 (10)	0.0288 (9)	0.0051 (7)	0.0011 (7)	−0.0033 (8)
C11	0.0196 (7)	0.0212 (7)	0.0185 (7)	−0.0034 (6)	−0.0012 (6)	0.0024 (6)
C12	0.0139 (7)	0.0218 (7)	0.0220 (8)	−0.0019 (6)	−0.0026 (6)	0.0070 (6)
C13	0.0180 (7)	0.0192 (7)	0.0226 (8)	0.0017 (6)	0.0034 (6)	0.0048 (6)
C14	0.0192 (7)	0.0170 (7)	0.0204 (7)	0.0020 (6)	−0.0029 (6)	0.0001 (6)
C15	0.0192 (7)	0.0229 (7)	0.0225 (8)	0.0002 (6)	−0.0024 (6)	0.0001 (6)
C16	0.0274 (8)	0.0217 (7)	0.0241 (8)	−0.0002 (6)	0.0025 (6)	0.0009 (6)
C17	0.0334 (9)	0.0241 (8)	0.0187 (8)	0.0049 (7)	−0.0005 (6)	0.0024 (6)
C18	0.0245 (8)	0.0252 (8)	0.0184 (7)	0.0060 (6)	−0.0058 (6)	−0.0033 (6)
C19	0.0185 (7)	0.0197 (7)	0.0199 (7)	0.0018 (6)	−0.0024 (6)	−0.0041 (6)
C20	0.0194 (8)	0.0232 (7)	0.0222 (8)	0.0032 (6)	−0.0072 (6)	−0.0029 (6)

Geometric parameters (Å, º)

O1—C2	1.4588 (18)	C9—H9a	1.002 (18)
O1—C3	1.3377 (18)	C9—H9b	1.001 (17)
O2—C3	1.2061 (19)	C9—C10	1.503 (2)
O3—C7	1.3355 (17)	C10—H10a	0.992 (19)
O3—C9	1.4583 (17)	C10—H10b	0.99 (2)
O4—C7	1.2100 (18)	C10—H10c	1.00 (2)
O5—C12	1.4025 (17)	C11—H11	0.964 (17)
O5—C14	1.3763 (18)	C11—C12	1.382 (2)
N1—C20	1.147 (2)	C12—C13	1.379 (2)
C1—H1a	0.99 (2)	C13—H13	0.936 (17)
C1—H1b	0.99 (2)	C14—C15	1.384 (2)
C1—H1c	1.00 (2)	C14—C19	1.399 (2)
C1—C2	1.498 (2)	C15—H15	0.973 (19)
C2—H2a	0.988 (19)	C15—C16	1.387 (2)
C2—H2b	0.98 (2)	C16—H16	0.988 (17)
C3—C4	1.492 (2)	C16—C17	1.388 (2)
C4—C5	1.391 (2)	C17—H17	0.950 (19)
C4—C13	1.397 (2)	C17—C18	1.378 (2)
C5—H5	0.967 (17)	C18—H18	0.945 (17)
C5—C6	1.391 (2)	C18—C19	1.398 (2)
C6—C7	1.493 (2)	C19—C20	1.436 (2)
C6—C11	1.395 (2)
C3—O1—C2	116.50 (12)	C10—C9—H9b	112.9 (10)
C9—O3—C7	115.44 (11)	H10a—C10—C9	109.7 (11)
C14—O5—C12	116.74 (11)	H10b—C10—C9	110.6 (11)
H1b—C1—H1a	108.8 (16)	H10b—C10—H10a	109.5 (15)
H1c—C1—H1a	108.1 (16)	H10c—C10—C9	108.3 (12)
H1c—C1—H1b	107.9 (17)	H10c—C10—H10a	110.4 (16)
C2—C1—H1a	110.9 (11)	H10c—C10—H10b	108.3 (16)
C2—C1—H1b	110.5 (12)	H11—C11—C6	121.8 (10)
C2—C1—H1c	110.5 (12)	C12—C11—C6	118.62 (14)
C1—C2—O1	110.56 (13)	C12—C11—H11	119.5 (10)
H2a—C2—O1	108.7 (10)	C11—C12—O5	119.28 (13)
H2a—C2—C1	111.7 (11)	C13—C12—O5	118.64 (13)
H2b—C2—O1	103.5 (11)	C13—C12—C11	122.08 (13)
H2b—C2—C1	111.8 (11)	C12—C13—C4	118.85 (14)
H2b—C2—H2a	110.3 (16)	H13—C13—C4	120.5 (10)
O2—C3—O1	124.32 (14)	H13—C13—C12	120.7 (10)
C4—C3—O1	112.32 (12)	C15—C14—O5	124.64 (13)
C4—C3—O2	123.35 (14)	C19—C14—O5	115.53 (13)
C5—C4—C3	122.10 (13)	C19—C14—C15	119.83 (14)
C13—C4—C3	117.47 (13)	H15—C15—C14	119.3 (11)
C13—C4—C5	120.30 (14)	C16—C15—C14	119.51 (14)
H5—C5—C4	120.5 (10)	C16—C15—H15	121.2 (11)
C6—C5—C4	119.60 (13)	H16—C16—C15	118.6 (10)
C6—C5—H5	119.9 (10)	C17—C16—C15	121.22 (15)
C7—C6—C5	122.14 (13)	C17—C16—H16	120.2 (10)
C11—C6—C5	120.52 (14)	H17—C17—C16	120.5 (11)
C11—C6—C7	117.28 (13)	C18—C17—C16	119.28 (15)
O4—C7—O3	124.15 (13)	C18—C17—H17	120.3 (11)
C6—C7—O3	112.38 (12)	H18—C18—C17	119.8 (10)
C6—C7—O4	123.46 (13)	C19—C18—C17	120.36 (14)
H9a—C9—O3	107.7 (10)	C19—C18—H18	119.8 (10)
H9b—C9—O3	107.3 (10)	C18—C19—C14	119.78 (14)
H9b—C9—H9a	109.9 (14)	C20—C19—C14	119.90 (13)
C10—C9—O3	106.54 (13)	C20—C19—C18	120.31 (13)
C10—C9—H9a	112.2 (10)	C19—C20—N1	178.46 (16)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C4–C6/C11–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O4^i	0.98 (2)	2.50 (2)	3.2071 (2)	128 (1)
C13—H13···O4^ii	0.936 (16)	2.514 (16)	3.4179 (2)	163.5 (12)
C16—H16···O2^iii	0.997 (17)	2.516 (17)	3.1941 (2)	125.7 (13)
C18—H18···N1^iv	0.945 (17)	2.629 (17)	3.430 (2)	143.0 (13)
C10—H10C···Cg1^v	1.00 (2)	2.96 (2)	3.7893 (19)	140 (2)

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