Dimethyl 5-(4-phenyl-1H-1,2,3-triazol-1-yl)benzene-1,3-dicarboxyl­ate

The cyclo­addition reaction of 3,5-dicarboxy­phenyl azide and phenyl­acetyl­ene, followed by esterification with methanol produced the title compound, C₁₈H₁₅N₃O₄. The mol­ecular skeleton is essentially planar.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.056
• wR factor = 0.179
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H19B   ..  H19B    ..       2.09 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: WinAFC (Rigaku, 2002); cell refinement: WinAFC; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXTL (Siemens, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL.

Dimethyl 5-(4-phenyl-1H-1,2,3-triazol-1-yl)benzene-1,3-dicarboxylate

Crystal data

C18H15O4N3	Z = 2
Mr = 337.33	F(000) = 352
Triclinic, P1	Dx = 1.410 Mg m^−3
a = 8.758 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.718 (2) Å	Cell parameters from 3217 reflections
c = 10.197 (2) Å	θ = 30.6–34.1°
α = 80.696 (19)°	µ = 0.10 mm^−1
β = 69.50 (2)°	T = 293 K
γ = 79.47 (2)°	Prism, colorless
V = 794.8 (4) Å^3	0.18 × 0.16 × 0.10 mm

Data collection

Rigaku AFC-7R diffractometer	2132 reflections with I > 2σ(I)
Radiation source: rotating-anode generator	Rint = 0.016
Graphite monochromator	θmax = 25.5°, θmin = 2.1°
ω–2θ scans	h = −10→3
Absorption correction: ψ scan (SBSCOR; Rigaku, 2002)	k = −11→11
Tmin = 0.986, Tmax = 0.999	l = −12→11
3217 measured reflections	3 standard reflections every 200 reflections
2962 independent reflections	intensity decay: none

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.179	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.12P)^2 + 0.0605P] where P = (Fo^2 + 2Fc^2)/3
2962 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.29 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
C11	0.1779 (3)	0.5823 (2)	0.3247 (2)	0.0434 (6)
C12	0.1698 (3)	0.5818 (3)	0.1913 (3)	0.0470 (6)
H12A	0.0969	0.6513	0.1577	0.056*
C13	0.2694 (3)	0.4786 (2)	0.1071 (2)	0.0441 (6)
C14	0.3775 (3)	0.3779 (2)	0.1550 (2)	0.0433 (5)
H14A	0.4431	0.3062	0.0983	0.052*
C15	0.3889 (3)	0.3828 (2)	0.2863 (2)	0.0435 (6)
C16	0.2890 (3)	0.4855 (2)	0.3718 (2)	0.0458 (6)
H16A	0.2973	0.4888	0.4617	0.055*
C17	0.2538 (3)	0.4822 (3)	−0.0350 (3)	0.0518 (6)
C18	0.5039 (3)	0.2796 (3)	0.3433 (2)	0.0468 (6)
C19	0.6654 (4)	0.0555 (3)	0.3247 (3)	0.0744 (9)
H19A	0.6976	−0.0192	0.2669	0.112*
H19B	0.6075	0.0216	0.4187	0.112*
H19C	0.7605	0.0911	0.3227	0.112*
C20	0.3269 (4)	0.3608 (4)	−0.2352 (3)	0.0737 (9)
H20A	0.3925	0.2773	−0.2712	0.111*
H20B	0.3647	0.4402	−0.2983	0.111*
H20C	0.2154	0.3582	−0.2251	0.111*
C21	0.0695 (3)	0.7179 (2)	0.5365 (2)	0.0486 (6)
H21A	0.1481	0.6823	0.5827	0.058*
C22	−0.0659 (3)	0.8154 (2)	0.5799 (2)	0.0454 (6)
C23	−0.1303 (3)	0.8908 (2)	0.7063 (2)	0.0455 (6)
C24	−0.0749 (3)	0.8464 (3)	0.8191 (3)	0.0552 (6)
H24A	0.0057	0.7658	0.8155	0.066*
C25	−0.1351 (4)	0.9175 (3)	0.9373 (3)	0.0685 (8)
H25A	−0.0952	0.8864	1.0140	0.082*
C26	−0.2528 (4)	1.0333 (3)	0.9442 (3)	0.0728 (9)
H26A	−0.2935	1.0827	1.0255	0.087*
C27	−0.3112 (4)	1.0776 (3)	0.8347 (3)	0.0695 (8)
H27A	−0.3939	1.1569	0.8407	0.083*
C28	−0.2506 (3)	1.0075 (3)	0.7142 (3)	0.0555 (7)
H28A	−0.2910	1.0391	0.6379	0.067*
N1	0.0684 (2)	0.6826 (2)	0.4143 (2)	0.0470 (5)
N2	−0.0635 (3)	0.7549 (2)	0.3824 (2)	0.0569 (6)
N3	−0.1440 (3)	0.8348 (2)	0.4824 (2)	0.0564 (6)
O1	0.1772 (3)	0.5758 (3)	−0.0857 (2)	0.0927 (8)
O2	0.3392 (2)	0.37120 (19)	−0.09989 (17)	0.0581 (5)
O3	0.5428 (2)	0.2960 (2)	0.44130 (19)	0.0675 (6)
O4	0.5597 (2)	0.16700 (18)	0.27285 (18)	0.0562 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0427 (13)	0.0467 (13)	0.0432 (12)	−0.0019 (10)	−0.0152 (10)	−0.0136 (10)
C12	0.0467 (13)	0.0502 (13)	0.0467 (13)	0.0008 (11)	−0.0210 (11)	−0.0082 (10)
C13	0.0453 (13)	0.0504 (14)	0.0405 (12)	−0.0065 (11)	−0.0169 (10)	−0.0096 (10)
C14	0.0432 (13)	0.0484 (13)	0.0399 (12)	−0.0016 (10)	−0.0148 (10)	−0.0120 (10)
C15	0.0467 (13)	0.0482 (13)	0.0390 (12)	−0.0015 (10)	−0.0181 (10)	−0.0112 (10)
C16	0.0493 (13)	0.0516 (13)	0.0415 (12)	−0.0019 (11)	−0.0197 (11)	−0.0137 (10)
C17	0.0535 (15)	0.0610 (16)	0.0471 (14)	−0.0020 (12)	−0.0260 (12)	−0.0078 (12)
C18	0.0474 (13)	0.0543 (14)	0.0405 (12)	0.0037 (11)	−0.0173 (10)	−0.0154 (10)
C19	0.078 (2)	0.0727 (19)	0.0721 (19)	0.0218 (16)	−0.0354 (17)	−0.0174 (15)
C20	0.094 (2)	0.090 (2)	0.0508 (16)	−0.0134 (18)	−0.0359 (16)	−0.0199 (15)
C21	0.0475 (14)	0.0514 (14)	0.0524 (14)	0.0059 (11)	−0.0236 (11)	−0.0192 (11)
C22	0.0429 (13)	0.0462 (13)	0.0494 (13)	−0.0005 (10)	−0.0175 (11)	−0.0130 (10)
C23	0.0427 (13)	0.0453 (13)	0.0483 (13)	−0.0044 (10)	−0.0122 (11)	−0.0128 (10)
C24	0.0594 (15)	0.0535 (14)	0.0541 (15)	0.0007 (12)	−0.0233 (12)	−0.0090 (12)
C25	0.086 (2)	0.0706 (18)	0.0512 (16)	−0.0019 (16)	−0.0267 (15)	−0.0143 (13)
C26	0.083 (2)	0.076 (2)	0.0572 (17)	−0.0002 (17)	−0.0170 (16)	−0.0283 (15)
C27	0.0669 (18)	0.0631 (18)	0.0731 (19)	0.0141 (14)	−0.0180 (15)	−0.0296 (15)
C28	0.0528 (15)	0.0524 (14)	0.0623 (16)	0.0051 (12)	−0.0214 (13)	−0.0174 (12)
N1	0.0452 (11)	0.0516 (12)	0.0477 (11)	0.0045 (9)	−0.0211 (9)	−0.0148 (9)
N2	0.0512 (12)	0.0677 (14)	0.0557 (13)	0.0123 (10)	−0.0261 (10)	−0.0220 (11)
N3	0.0534 (12)	0.0633 (13)	0.0556 (13)	0.0109 (10)	−0.0241 (10)	−0.0221 (10)
O1	0.1146 (19)	0.1027 (17)	0.0661 (13)	0.0421 (15)	−0.0581 (14)	−0.0241 (12)
O2	0.0751 (12)	0.0638 (11)	0.0443 (9)	−0.0014 (9)	−0.0303 (9)	−0.0163 (8)
O3	0.0755 (13)	0.0817 (14)	0.0561 (11)	0.0204 (10)	−0.0414 (10)	−0.0285 (10)
O4	0.0654 (11)	0.0535 (10)	0.0534 (10)	0.0150 (8)	−0.0296 (9)	−0.0193 (8)

Geometric parameters (Å, º)

C11—C16	1.382 (3)	C20—H20A	0.950
C11—C12	1.387 (3)	C20—H20B	0.950
C11—N1	1.428 (3)	C20—H20C	0.950
C12—C13	1.392 (3)	C21—N1	1.348 (3)
C12—H12A	0.950	C21—C22	1.363 (3)
C13—C14	1.386 (3)	C21—H21A	0.950
C13—C17	1.497 (3)	C22—N3	1.363 (3)
C14—C15	1.386 (3)	C22—C23	1.470 (3)
C14—H14A	0.950	C23—C24	1.378 (3)
C15—C16	1.397 (3)	C23—C28	1.391 (4)
C15—C18	1.487 (3)	C24—C25	1.378 (4)
C16—H16A	0.950	C24—H24A	0.950
C17—O1	1.188 (3)	C25—C26	1.372 (4)
C17—O2	1.323 (3)	C25—H25A	0.950
C18—O3	1.205 (3)	C26—C27	1.363 (4)
C18—O4	1.328 (3)	C26—H26A	0.950
C19—O4	1.450 (3)	C27—C28	1.392 (4)
C19—H19A	0.950	C27—H27A	0.950
C19—H19B	0.950	C28—H28A	0.950
C19—H19C	0.950	N1—N2	1.352 (3)
C20—O2	1.441 (3)	N2—N3	1.301 (3)
C16—C11—C12	120.6 (2)	H20A—C20—H20C	109.5
C16—C11—N1	119.9 (2)	H20B—C20—H20C	109.5
C12—C11—N1	119.4 (2)	N1—C21—C22	105.5 (2)
C13—C12—C11	119.5 (2)	N1—C21—H21A	127.2
C13—C12—H12A	120.3	C22—C21—H21A	127.2
C11—C12—H12A	120.3	N3—C22—C21	107.5 (2)
C12—C13—C14	120.5 (2)	N3—C22—C23	121.9 (2)
C12—C13—C17	117.1 (2)	C21—C22—C23	130.6 (2)
C14—C13—C17	122.4 (2)	C24—C23—C28	119.0 (2)
C15—C14—C13	119.5 (2)	C24—C23—C22	120.9 (2)
C15—C14—H14A	120.3	C28—C23—C22	120.1 (2)
C13—C14—H14A	120.3	C23—C24—C25	120.8 (3)
C14—C15—C16	120.5 (2)	C23—C24—H24A	119.6
C14—C15—C18	122.3 (2)	C25—C24—H24A	119.6
C16—C15—C18	117.2 (2)	C26—C25—C24	120.1 (3)
C11—C16—C15	119.4 (2)	C26—C25—H25A	120.0
C11—C16—H16A	120.3	C24—C25—H25A	120.0
C15—C16—H16A	120.3	C27—C26—C25	120.1 (3)
O1—C17—O2	123.6 (2)	C27—C26—H26A	120.0
O1—C17—C13	124.0 (2)	C25—C26—H26A	120.0
O2—C17—C13	112.3 (2)	C26—C27—C28	120.5 (3)
O3—C18—O4	123.8 (2)	C26—C27—H27A	119.8
O3—C18—C15	124.1 (2)	C28—C27—H27A	119.8
O4—C18—C15	112.07 (19)	C23—C28—C27	119.6 (3)
O4—C19—H19A	109.5	C23—C28—H28A	120.2
O4—C19—H19B	109.5	C27—C28—H28A	120.2
H19A—C19—H19B	109.5	C21—N1—N2	110.19 (19)
O4—C19—H19C	109.5	C21—N1—C11	130.1 (2)
H19A—C19—H19C	109.5	N2—N1—C11	119.72 (19)
H19B—C19—H19C	109.5	N3—N2—N1	107.04 (19)
O2—C20—H20A	109.5	N2—N3—C22	109.75 (19)
O2—C20—H20B	109.5	C17—O2—C20	116.9 (2)
H20A—C20—H20B	109.5	C18—O4—C19	116.7 (2)
O2—C20—H20C	109.5