Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-chloro­phen­yl)-5-cyclo­propyl-1-(4-meth­oxy­phen­yl)-1H-1,2,3-triazole-4-carboxamide

The title compound was obtained via a two-step synthesis involving the enole-mediated click Dimroth reaction of 4-azido­anisole with methyl 3-cyclo­propyl-3-oxo­propano­ate leading to the 5-cyclo­propyl-1-(4-meth­oxy­phen­yl)-1H-1,2,3-triazole-4-carb­oxy­lic acid and subsequent acid amidation with 4-chloro­aniline by 1,1′-carbonyl­diimidazole (CDI). In the extended structure, two mol­ecules arranged in a near coplanar position relative to the triazole ring planes are inter­connected by N—H...N and C—H...N hydrogen bonds into a homodimer. The dimers are linked by C—H...O inter­actions into ribbons.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.053
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        44% Check
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1       --C10      .        6.4 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2       --C3       .        6.5 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8       --C10      .        5.5 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11      --C13      .        7.0 s.u.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         N2 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4       ..N2       .       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19      ..N2       .       2.68 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     27.191 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.172 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.291 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         30 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  12 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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2005); cell refinement: CrysAlis PRO (Oxford Diffraction, 2005); data reduction: CrysAlis PRO (Oxford Diffraction, 2005); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

N-(4-Chlorophenyl)-5-cyclopropyl-1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxamide

Crystal data

C19H17ClN4O2	F(000) = 768
Mr = 368.82	Dx = 1.368 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.5673 (4) Å	Cell parameters from 1540 reflections
b = 8.0182 (3) Å	θ = 0.9–1.0°
c = 21.2318 (10) Å	µ = 0.24 mm^−1
β = 95.282 (4)°	T = 293 K
V = 1791.35 (13) Å^3	Prism, colourless
Z = 4	0.5 × 0.08 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer	1534 reflections with I > 2σ(I)
ω scans	Rint = 0.046
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005)	θmax = 26.0°, θmin = 2.7°
Tmin = 0.890, Tmax = 0.982	h = −12→12
10913 measured reflections	k = −5→9
3475 independent reflections	l = −25→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.053	w = 1/[σ^2(Fo^2) + (0.0071P)^2 + 0.050P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3475 reflections	Δρmax = 0.14 e Å^−3
236 parameters	Δρmin = −0.19 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.

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

	x	y	z	Uiso*/Ueq
Cl1	1.19945 (6)	0.04278 (8)	0.35044 (3)	0.0860 (2)
O1	0.80102 (13)	0.41861 (18)	0.54511 (7)	0.0627 (5)
O2	0.01792 (15)	0.44313 (19)	0.73741 (7)	0.0686 (5)
N4	0.75389 (15)	0.1763 (2)	0.49150 (8)	0.0524 (5)
H4	0.695819	0.101374	0.485272	0.063*
N1	0.43143 (16)	0.3069 (2)	0.60195 (9)	0.0556 (5)
C14	0.8626 (2)	0.1540 (2)	0.45845 (11)	0.0443 (6)
C1	0.3243 (2)	0.3477 (2)	0.63661 (12)	0.0492 (6)
C9	0.5403 (2)	0.3903 (2)	0.59331 (10)	0.0479 (6)
C4	0.1154 (2)	0.4142 (3)	0.70082 (12)	0.0512 (6)
C10	0.7294 (2)	0.3016 (3)	0.53206 (11)	0.0505 (6)
N3	0.53626 (18)	0.1428 (2)	0.54590 (10)	0.0763 (7)
C15	0.9796 (2)	0.2218 (2)	0.47738 (10)	0.0520 (6)
H15	0.989197	0.290445	0.512804	0.062*
C8	0.6050 (2)	0.2842 (3)	0.55768 (11)	0.0486 (6)
C3	0.11310 (19)	0.4532 (2)	0.63777 (11)	0.0546 (6)
H3	0.041147	0.501519	0.616770	0.066*
N2	0.43009 (18)	0.1551 (2)	0.57229 (11)	0.0831 (7)
C19	0.84942 (19)	0.0551 (3)	0.40452 (10)	0.0539 (6)
H19	0.770296	0.011077	0.390662	0.065*
C2	0.2188 (2)	0.4199 (3)	0.60555 (10)	0.0546 (6)
H2	0.218048	0.446667	0.562890	0.066*
C16	1.0831 (2)	0.1881 (3)	0.44386 (11)	0.0573 (7)
H16	1.162198	0.233351	0.456901	0.069*
C11	0.57821 (19)	0.5584 (3)	0.61661 (11)	0.0596 (6)
H11	0.658079	0.596910	0.601492	0.072*
C18	0.9525 (2)	0.0218 (2)	0.37150 (10)	0.0585 (7)
H18	0.943421	−0.045418	0.335686	0.070*
C17	1.0685 (2)	0.0881 (3)	0.39158 (11)	0.0533 (6)
C5	0.2213 (2)	0.3398 (3)	0.73129 (11)	0.0635 (7)
H5	0.222148	0.312257	0.773873	0.076*
C6	0.3263 (2)	0.3056 (3)	0.69943 (12)	0.0623 (7)
H6	0.397430	0.254642	0.720160	0.075*
C13	0.5580 (2)	0.6216 (3)	0.68014 (12)	0.0782 (8)
H13A	0.511849	0.550992	0.707204	0.094*
H13B	0.625552	0.687084	0.702118	0.094*
C12	0.4869 (2)	0.6965 (3)	0.62524 (13)	0.0809 (8)
H12A	0.510672	0.808059	0.613084	0.097*
H12B	0.396882	0.671863	0.618174	0.097*
C7	−0.0993 (2)	0.4984 (3)	0.70643 (12)	0.0970 (9)
H7A	−0.128382	0.419658	0.674241	0.146*
H7B	−0.087613	0.605304	0.687433	0.146*
H7C	−0.161144	0.507674	0.736641	0.146*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0723 (5)	0.0988 (5)	0.0925 (5)	0.0004 (4)	0.0379 (4)	−0.0087 (4)
O1	0.0573 (10)	0.0568 (10)	0.0765 (12)	−0.0187 (8)	0.0189 (9)	−0.0171 (9)
O2	0.0585 (11)	0.0879 (12)	0.0627 (12)	0.0026 (9)	0.0231 (10)	0.0082 (9)
N4	0.0475 (12)	0.0478 (12)	0.0639 (14)	−0.0110 (9)	0.0167 (11)	−0.0108 (10)
N1	0.0512 (13)	0.0499 (12)	0.0682 (15)	−0.0072 (11)	0.0186 (12)	−0.0094 (11)
C14	0.0454 (15)	0.0413 (14)	0.0468 (15)	−0.0044 (11)	0.0087 (14)	−0.0008 (12)
C1	0.0468 (16)	0.0458 (14)	0.0565 (18)	−0.0048 (12)	0.0130 (15)	−0.0036 (13)
C9	0.0480 (15)	0.0428 (14)	0.0534 (16)	−0.0059 (12)	0.0067 (14)	−0.0038 (12)
C4	0.0516 (17)	0.0527 (15)	0.0507 (17)	−0.0039 (12)	0.0127 (15)	0.0017 (13)
C10	0.0562 (17)	0.0463 (15)	0.0501 (16)	0.0002 (13)	0.0103 (15)	−0.0024 (13)
N3	0.0591 (14)	0.0633 (15)	0.1115 (19)	−0.0171 (11)	0.0347 (14)	−0.0363 (12)
C15	0.0512 (15)	0.0488 (15)	0.0553 (18)	−0.0033 (12)	0.0013 (15)	−0.0112 (12)
C8	0.0436 (15)	0.0443 (15)	0.0589 (17)	−0.0099 (12)	0.0110 (14)	−0.0123 (12)
C3	0.0493 (15)	0.0617 (15)	0.0540 (17)	0.0043 (12)	0.0109 (14)	0.0055 (13)
N2	0.0665 (16)	0.0618 (14)	0.127 (2)	−0.0215 (11)	0.0420 (15)	−0.0392 (13)
C19	0.0503 (15)	0.0561 (14)	0.0564 (16)	−0.0130 (12)	0.0109 (14)	−0.0093 (13)
C2	0.0619 (17)	0.0589 (15)	0.0434 (15)	−0.0041 (14)	0.0065 (15)	0.0055 (12)
C16	0.0456 (16)	0.0629 (16)	0.0644 (19)	−0.0073 (13)	0.0105 (15)	−0.0063 (14)
C11	0.0580 (16)	0.0533 (15)	0.0704 (18)	−0.0040 (13)	0.0210 (14)	−0.0185 (14)
C18	0.0657 (17)	0.0595 (16)	0.0520 (16)	−0.0095 (14)	0.0143 (15)	−0.0114 (12)
C17	0.0523 (16)	0.0561 (15)	0.0542 (17)	0.0004 (13)	0.0198 (14)	0.0034 (13)
C5	0.0602 (18)	0.0838 (18)	0.0474 (17)	−0.0001 (14)	0.0095 (16)	0.0168 (14)
C6	0.0478 (17)	0.0717 (17)	0.067 (2)	0.0024 (13)	0.0025 (16)	0.0143 (15)
C13	0.083 (2)	0.0669 (18)	0.085 (2)	−0.0152 (15)	0.0110 (19)	−0.0197 (16)
C12	0.073 (2)	0.0489 (16)	0.119 (2)	0.0045 (14)	−0.0003 (19)	−0.0099 (17)
C7	0.0580 (18)	0.136 (3)	0.102 (2)	0.0258 (17)	0.0314 (17)	0.0219 (19)

Geometric parameters (Å, º)

Cl1—C17	1.742 (2)	C3—H3	0.9300
O1—C10	1.221 (2)	C3—C2	1.389 (3)
O2—C4	1.366 (2)	C19—H19	0.9300
O2—C7	1.419 (2)	C19—C18	1.375 (3)
N4—H4	0.8600	C2—H2	0.9300
N4—C14	1.412 (2)	C16—H16	0.9300
N4—C10	1.364 (2)	C16—C17	1.367 (3)
N1—C1	1.443 (2)	C11—H11	0.9800
N1—C9	1.358 (2)	C11—C13	1.475 (3)
N1—N2	1.370 (2)	C11—C12	1.491 (3)
C14—C15	1.376 (3)	C18—H18	0.9300
C14—C19	1.389 (2)	C18—C17	1.367 (3)
C1—C2	1.370 (3)	C5—H5	0.9300
C1—C6	1.374 (3)	C5—C6	1.379 (3)
C9—C8	1.363 (2)	C6—H6	0.9300
C9—C11	1.478 (3)	C13—H13A	0.9700
C4—C3	1.373 (3)	C13—H13B	0.9700
C4—C5	1.376 (3)	C13—C12	1.457 (3)
C10—C8	1.476 (3)	C12—H12A	0.9700
N3—C8	1.357 (2)	C12—H12B	0.9700
N3—N2	1.303 (2)	C7—H7A	0.9600
C15—H15	0.9300	C7—H7B	0.9600
C15—C16	1.385 (3)	C7—H7C	0.9600
C4—O2—C7	117.47 (18)	C15—C16—H16	120.1
C14—N4—H4	115.9	C17—C16—C15	119.8 (2)
C10—N4—H4	115.9	C17—C16—H16	120.1
C10—N4—C14	128.10 (18)	C9—C11—H11	113.1
C9—N1—C1	132.18 (19)	C9—C11—C12	124.1 (2)
C9—N1—N2	110.40 (17)	C13—C11—C9	124.2 (2)
N2—N1—C1	117.40 (17)	C13—C11—H11	113.1
C15—C14—N4	123.7 (2)	C13—C11—C12	58.84 (14)
C15—C14—C19	119.1 (2)	C12—C11—H11	113.1
C19—C14—N4	117.2 (2)	C19—C18—H18	120.2
C2—C1—N1	119.5 (2)	C17—C18—C19	119.7 (2)
C2—C1—C6	120.7 (2)	C17—C18—H18	120.2
C6—C1—N1	119.8 (2)	C16—C17—Cl1	119.63 (19)
N1—C9—C8	103.98 (17)	C16—C17—C18	120.8 (2)
N1—C9—C11	127.6 (2)	C18—C17—Cl1	119.56 (18)
C8—C9—C11	128.4 (2)	C4—C5—H5	119.6
O2—C4—C3	124.7 (2)	C4—C5—C6	120.8 (2)
O2—C4—C5	115.5 (2)	C6—C5—H5	119.6
C3—C4—C5	119.9 (2)	C1—C6—C5	119.1 (2)
O1—C10—N4	124.08 (19)	C1—C6—H6	120.5
O1—C10—C8	122.9 (2)	C5—C6—H6	120.5
N4—C10—C8	113.0 (2)	C11—C13—H13A	117.7
N2—N3—C8	108.94 (17)	C11—C13—H13B	117.7
C14—C15—H15	119.9	H13A—C13—H13B	114.8
C14—C15—C16	120.2 (2)	C12—C13—C11	61.14 (16)
C16—C15—H15	119.9	C12—C13—H13A	117.7
C9—C8—C10	130.9 (2)	C12—C13—H13B	117.7
N3—C8—C9	109.70 (18)	C11—C12—H12A	117.8
N3—C8—C10	119.4 (2)	C11—C12—H12B	117.8
C4—C3—H3	120.2	C13—C12—C11	60.02 (15)
C4—C3—C2	119.6 (2)	C13—C12—H12A	117.8
C2—C3—H3	120.2	C13—C12—H12B	117.8
N3—N2—N1	106.97 (17)	H12A—C12—H12B	114.9
C14—C19—H19	119.8	O2—C7—H7A	109.5
C18—C19—C14	120.4 (2)	O2—C7—H7B	109.5
C18—C19—H19	119.8	O2—C7—H7C	109.5
C1—C2—C3	120.0 (2)	H7A—C7—H7B	109.5
C1—C2—H2	120.0	H7A—C7—H7C	109.5
C3—C2—H2	120.0	H7B—C7—H7C	109.5
O1—C10—C8—C9	6.7 (4)	C4—C5—C6—C1	0.4 (3)
O1—C10—C8—N3	−173.6 (2)	C10—N4—C14—C15	23.3 (4)
O2—C4—C3—C2	179.10 (19)	C10—N4—C14—C19	−158.0 (2)
O2—C4—C5—C6	−179.5 (2)	C15—C14—C19—C18	1.7 (3)
N4—C14—C15—C16	177.1 (2)	C15—C16—C17—Cl1	−178.77 (17)
N4—C14—C19—C18	−177.10 (19)	C15—C16—C17—C18	0.6 (3)
N4—C10—C8—C9	−171.8 (2)	C8—C9—C11—C13	−139.8 (3)
N4—C10—C8—N3	7.9 (3)	C8—C9—C11—C12	147.4 (3)
N1—C1—C2—C3	177.23 (19)	C8—N3—N2—N1	−0.5 (3)
N1—C1—C6—C5	−177.6 (2)	C3—C4—C5—C6	0.8 (3)
N1—C9—C8—C10	179.6 (2)	N2—N1—C1—C2	−86.6 (2)
N1—C9—C8—N3	−0.1 (3)	N2—N1—C1—C6	89.8 (3)
N1—C9—C11—C13	41.2 (4)	N2—N1—C9—C8	−0.2 (2)
N1—C9—C11—C12	−31.6 (4)	N2—N1—C9—C11	179.1 (2)
C14—N4—C10—O1	1.2 (4)	N2—N3—C8—C9	0.4 (3)
C14—N4—C10—C8	179.7 (2)	N2—N3—C8—C10	−179.4 (2)
C14—C15—C16—C17	0.5 (3)	C19—C14—C15—C16	−1.6 (3)
C14—C19—C18—C17	−0.7 (3)	C19—C18—C17—Cl1	178.88 (17)
C1—N1—C9—C8	178.1 (2)	C19—C18—C17—C16	−0.5 (3)
C1—N1—C9—C11	−2.7 (4)	C2—C1—C6—C5	−1.2 (3)
C1—N1—N2—N3	−178.2 (2)	C11—C9—C8—C10	0.4 (4)
C9—N1—C1—C2	95.2 (3)	C11—C9—C8—N3	−179.3 (2)
C9—N1—C1—C6	−88.4 (3)	C5—C4—C3—C2	−1.2 (3)
C9—N1—N2—N3	0.4 (3)	C6—C1—C2—C3	0.8 (3)
C9—C11—C13—C12	−112.4 (3)	C7—O2—C4—C3	8.1 (3)
C9—C11—C12—C13	112.6 (3)	C7—O2—C4—C5	−171.63 (19)
C4—C3—C2—C1	0.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3	0.86	2.24	2.680 (3)	112
N4—H4···N2^i	0.86	2.68	3.491 (2)	157
C15—H15···O1	0.93	2.39	2.936 (2)	117
C19—H19···N2^i	0.93	2.68	3.475 (3)	144
C2—H2···O1^ii	0.93	2.53	3.439 (3)	167
C11—H11···O1	0.98	2.47	3.124 (2)	124

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