6-tert-Butyl-4-[(4-hy­droxy­methyl-2H-1,2,3-triazol-2-yl)meth­yl]-2H-chromen-2-one

In the title compound, C₁₇H₁₉N₃O₃, the triazole ring and the chromene ring system [maximum deviation = 0.018 (2) Å for the O atom] bridged via a methyl­ene C atom, are inclined to one another by 73.2 (1)°. In the crystal, mol­ecules are linked by O—H...N hydrogen bonds, forming zigzag chains along [001]. The chains are linked by C—H...O hydrogen bonds, forming layers parallel to (010), and these layers are linked by C—H...π and π–π inter­actions [intercentroid distance = 3.557 (1) Å], forming a three-dimensional newwork. The hy­droxy­methyl group at the 4-position of the triazole ring is disordered over two sets of sites, with a refined occupancy ratio of 0.418 (11):0.584 (11).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.030
• wR factor = 0.080
• Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT915_ALERT_3_B No Flack x Check Done: Low Friedel Pair Coverage         15 %

Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 8 for a
            non-centrosymmetric structure, where ZMAX < 18
            sine(theta)/lambda                0.5847
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   6.9648
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5847
PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6]..      64.35 Degree
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.961 Note
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.11 Do !
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.15 Note
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C20 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.585         52 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         17 Note
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.500 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          9 Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         38 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still         100 %
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           4 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES .........          2 Note

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

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

---

Computing details

6-tert-Butyl-4-[(4-hydroxymethyl-2H-1,2,3-triazol-2-yl)methyl]-2H-chromen-2-one

Crystal data

C17H19N3O3	Dx = 1.315 Mg m^−3
Mr = 313.35	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna21	Cell parameters from 1581 reflections
a = 8.9099 (12) Å	θ = 7.2–64.4°
b = 24.550 (3) Å	µ = 0.75 mm^−1
c = 7.2359 (11) Å	T = 293 K
V = 1582.7 (4) Å^3	Block, colourless
Z = 4	0.32 × 0.22 × 0.12 mm
F(000) = 664

Data collection

Bruker X8 Proteum diffractometer	1565 reflections with I > 2σ(I)
Radiation source: Bruker MicroStar microfocus rotating anode	Rint = 0.022
Helios multilayer optics monochromator	θmax = 64.4°, θmin = 7.2°
Detector resolution: 18.4 pixels mm^-1	h = −10→9
φ and ω scans	k = −28→27
5136 measured reflections	l = −3→8
1581 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0492P)^2 + 0.1878P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1581 reflections	Δρmax = 0.10 e Å^−3
227 parameters	Δρmin = −0.11 e Å^−3
38 restraints	Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (5)

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. Refined as a 2-component inversion twin.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C12	0.1311 (2)	0.32195 (7)	0.4515 (3)	0.0390 (4)
N1	0.60931 (17)	0.47866 (6)	0.3641 (3)	0.0440 (4)
C11	0.2465 (2)	0.35946 (7)	0.4284 (3)	0.0362 (4)
H11	0.246706	0.381302	0.323334	0.043*
O16	0.47177 (19)	0.33551 (6)	0.8472 (3)	0.0573 (4)
C13	0.1364 (2)	0.28959 (8)	0.6120 (3)	0.0498 (5)
H13	0.060668	0.264168	0.631743	0.060*
C15	0.3613 (2)	0.33239 (8)	0.7134 (3)	0.0431 (5)
O19	0.6737 (2)	0.37446 (8)	0.9624 (3)	0.0858 (7)
C9	0.4845 (2)	0.40488 (8)	0.5398 (3)	0.0399 (5)
N4	0.7328 (2)	0.54936 (8)	0.4439 (3)	0.0576 (5)
C10	0.3626 (2)	0.36557 (7)	0.5575 (3)	0.0359 (4)
C2	0.7321 (2)	0.47844 (8)	0.2567 (3)	0.0438 (5)
H2	0.757906	0.453111	0.166558	0.053*
N5	0.6080 (2)	0.52202 (8)	0.4770 (3)	0.0578 (6)
C17	0.5846 (3)	0.37326 (9)	0.8355 (4)	0.0564 (6)
C8	0.4850 (2)	0.44007 (9)	0.3695 (4)	0.0472 (5)
H8A	0.490187	0.416841	0.261230	0.057*
H8B	0.391225	0.460096	0.363693	0.057*
C18	0.5886 (2)	0.40772 (9)	0.6742 (4)	0.0497 (5)
H18	0.666089	0.432863	0.662608	0.060*
C20	0.0017 (2)	0.31619 (8)	0.3138 (4)	0.0442 (5)
C23	0.0228 (3)	0.35213 (11)	0.1440 (4)	0.0645 (7)
H23A	0.023399	0.389703	0.180780	0.097*
H23B	−0.058150	0.345981	0.058916	0.097*
H23C	0.116334	0.343349	0.085332	0.097*
C21	−0.1441 (2)	0.33404 (11)	0.4108 (5)	0.0676 (7)
H21A	−0.135254	0.371364	0.448802	0.101*
H21B	−0.160897	0.311489	0.517178	0.101*
H21C	−0.226873	0.330379	0.326834	0.101*
C14	0.2491 (3)	0.29416 (9)	0.7405 (3)	0.0531 (5)
H14	0.250115	0.271857	0.844358	0.064*
C6A	0.957 (3)	0.5456 (15)	0.238 (6)	0.0620 (7)	0.418 (11)
H6A1	0.981776	0.528038	0.121698	0.074*	0.418 (11)
H6A2	0.947595	0.584396	0.215757	0.074*	0.418 (11)
O7A	1.0709 (6)	0.5357 (3)	0.3685 (13)	0.076 (3)	0.418 (11)
H7A	1.126711	0.562246	0.373797	0.113*	0.418 (11)
C6B	0.958 (2)	0.5453 (10)	0.243 (4)	0.0620 (7)	0.582 (11)
H6B1	0.949910	0.554755	0.113039	0.074*	0.582 (11)
H6B2	0.981856	0.578301	0.310511	0.074*	0.582 (11)
O7B	1.0773 (4)	0.5076 (3)	0.2653 (10)	0.0883 (19)	0.582 (11)
H7B	1.086999	0.489670	0.170471	0.132*	0.582 (11)
C3	0.8105 (2)	0.52358 (8)	0.3088 (3)	0.0456 (5)
C22	−0.0126 (3)	0.25684 (10)	0.2520 (5)	0.0696 (7)
H22A	−0.097310	0.253182	0.170927	0.104*
H22B	−0.026487	0.233981	0.358248	0.104*
H22C	0.077008	0.246108	0.187940	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C12	0.0373 (9)	0.0366 (8)	0.0432 (11)	−0.0002 (7)	0.0003 (10)	−0.0017 (9)
N1	0.0402 (8)	0.0519 (9)	0.0397 (10)	−0.0097 (6)	−0.0021 (8)	−0.0082 (9)
C11	0.0372 (10)	0.0377 (8)	0.0338 (11)	0.0004 (7)	−0.0020 (8)	0.0010 (8)
O16	0.0706 (10)	0.0580 (8)	0.0434 (9)	0.0082 (7)	−0.0239 (9)	0.0048 (8)
C13	0.0542 (12)	0.0445 (10)	0.0508 (13)	−0.0063 (9)	0.0027 (11)	0.0063 (10)
C15	0.0509 (11)	0.0427 (10)	0.0356 (11)	0.0083 (8)	−0.0067 (10)	−0.0006 (9)
O19	0.0912 (14)	0.0893 (12)	0.0769 (14)	0.0107 (10)	−0.0554 (13)	−0.0029 (12)
C9	0.0339 (9)	0.0470 (10)	0.0388 (11)	0.0024 (7)	−0.0050 (9)	−0.0057 (9)
N4	0.0570 (10)	0.0593 (10)	0.0566 (12)	−0.0176 (8)	0.0027 (11)	−0.0126 (10)
C10	0.0372 (9)	0.0382 (8)	0.0323 (10)	0.0039 (7)	−0.0032 (9)	−0.0021 (8)
C2	0.0435 (11)	0.0489 (10)	0.0389 (11)	−0.0026 (8)	0.0026 (9)	−0.0026 (9)
N5	0.0543 (10)	0.0618 (11)	0.0573 (14)	−0.0144 (9)	0.0083 (10)	−0.0190 (11)
C17	0.0573 (13)	0.0580 (12)	0.0538 (15)	0.0130 (10)	−0.0274 (13)	−0.0112 (12)
C8	0.0399 (10)	0.0591 (11)	0.0426 (12)	−0.0140 (8)	−0.0071 (10)	0.0021 (11)
C18	0.0420 (10)	0.0566 (11)	0.0505 (13)	0.0010 (9)	−0.0124 (11)	−0.0103 (11)
C20	0.0354 (9)	0.0446 (10)	0.0525 (13)	−0.0069 (7)	−0.0045 (10)	0.0017 (10)
C23	0.0521 (12)	0.0841 (16)	0.0572 (16)	−0.0168 (12)	−0.0195 (13)	0.0131 (14)
C21	0.0410 (11)	0.0788 (15)	0.083 (2)	−0.0002 (10)	0.0005 (14)	−0.0012 (15)
C14	0.0702 (13)	0.0482 (11)	0.0409 (12)	0.0017 (10)	−0.0016 (11)	0.0120 (10)
C6A	0.0507 (13)	0.0732 (15)	0.062 (2)	−0.0176 (11)	0.0022 (14)	0.0079 (14)
O7A	0.049 (3)	0.085 (4)	0.092 (6)	−0.014 (3)	−0.016 (3)	0.022 (4)
C6B	0.0507 (13)	0.0732 (15)	0.062 (2)	−0.0176 (11)	0.0022 (14)	0.0079 (14)
O7B	0.0576 (19)	0.094 (3)	0.113 (4)	−0.0042 (19)	0.029 (2)	−0.010 (3)
C3	0.0431 (10)	0.0502 (10)	0.0434 (12)	−0.0084 (8)	−0.0005 (10)	0.0036 (10)
C22	0.0727 (15)	0.0572 (13)	0.0789 (19)	−0.0102 (11)	−0.0213 (16)	−0.0117 (13)

Geometric parameters (Å, º)

C12—C11	1.391 (3)	C18—H18	0.9300
C12—C13	1.408 (3)	C20—C23	1.524 (4)
C12—C20	1.531 (3)	C20—C22	1.529 (3)
N1—C2	1.342 (3)	C20—C21	1.540 (3)
N1—N5	1.342 (2)	C23—H23A	0.9600
N1—C8	1.458 (2)	C23—H23B	0.9600
C11—C10	1.402 (3)	C23—H23C	0.9600
C11—H11	0.9300	C21—H21A	0.9600
O16—C17	1.370 (3)	C21—H21B	0.9600
O16—C15	1.383 (3)	C21—H21C	0.9600
C13—C14	1.373 (3)	C14—H14	0.9300
C13—H13	0.9300	C6A—O7A	1.411 (18)
C15—C14	1.385 (3)	C6A—C3	1.50 (4)
C15—C10	1.391 (3)	C6A—H6A1	0.9700
O19—C17	1.214 (3)	C6A—H6A2	0.9700
C9—C18	1.346 (3)	O7A—H7A	0.8200
C9—C10	1.458 (3)	C6B—O7B	1.416 (15)
C9—C8	1.505 (3)	C6B—C3	1.50 (3)
N4—N5	1.320 (3)	C6B—H6B1	0.9700
N4—C3	1.355 (3)	C6B—H6B2	0.9700
C2—C3	1.363 (3)	O7B—H7B	0.8200
C2—H2	0.9300	C22—H22A	0.9600
C17—C18	1.442 (4)	C22—H22B	0.9600
C8—H8A	0.9700	C22—H22C	0.9600
C8—H8B	0.9700
C11—C12—C13	116.66 (19)	C22—C20—C21	109.52 (19)
C11—C12—C20	122.66 (18)	C12—C20—C21	108.2 (2)
C13—C12—C20	120.67 (17)	C20—C23—H23A	109.5
C2—N1—N5	111.27 (16)	C20—C23—H23B	109.5
C2—N1—C8	129.22 (18)	H23A—C23—H23B	109.5
N5—N1—C8	119.51 (17)	C20—C23—H23C	109.5
C12—C11—C10	122.41 (19)	H23A—C23—H23C	109.5
C12—C11—H11	118.8	H23B—C23—H23C	109.5
C10—C11—H11	118.8	C20—C21—H21A	109.5
C17—O16—C15	121.1 (2)	C20—C21—H21B	109.5
C14—C13—C12	122.45 (19)	H21A—C21—H21B	109.5
C14—C13—H13	118.8	C20—C21—H21C	109.5
C12—C13—H13	118.8	H21A—C21—H21C	109.5
O16—C15—C14	116.9 (2)	H21B—C21—H21C	109.5
O16—C15—C10	121.97 (18)	C13—C14—C15	119.2 (2)
C14—C15—C10	121.14 (19)	C13—C14—H14	120.4
C18—C9—C10	118.9 (2)	C15—C14—H14	120.4
C18—C9—C8	124.07 (18)	O7A—C6A—C3	110 (3)
C10—C9—C8	116.99 (17)	O7A—C6A—H6A1	109.8
N5—N4—C3	108.91 (18)	C3—C6A—H6A1	109.8
C15—C10—C11	118.14 (17)	O7A—C6A—H6A2	109.8
C15—C10—C9	117.70 (18)	C3—C6A—H6A2	109.8
C11—C10—C9	124.15 (18)	H6A1—C6A—H6A2	108.2
N1—C2—C3	104.73 (19)	C6A—O7A—H7A	109.5
N1—C2—H2	127.6	O7B—C6B—C3	112.9 (18)
C3—C2—H2	127.6	O7B—C6B—H6B1	109.0
N4—N5—N1	106.58 (18)	C3—C6B—H6B1	109.0
O19—C17—O16	116.7 (3)	O7B—C6B—H6B2	109.0
O19—C17—C18	125.6 (2)	C3—C6B—H6B2	109.0
O16—C17—C18	117.72 (19)	H6B1—C6B—H6B2	107.8
N1—C8—C9	113.38 (18)	C6B—O7B—H7B	109.5
N1—C8—H8A	108.9	N4—C3—C2	108.50 (18)
C9—C8—H8A	108.9	N4—C3—C6B	120.9 (11)
N1—C8—H8B	108.9	C2—C3—C6B	130.6 (11)
C9—C8—H8B	108.9	N4—C3—C6A	121.5 (15)
H8A—C8—H8B	107.7	C2—C3—C6A	130.0 (15)
C9—C18—C17	122.5 (2)	C20—C22—H22A	109.5
C9—C18—H18	118.7	C20—C22—H22B	109.5
C17—C18—H18	118.7	H22A—C22—H22B	109.5
C23—C20—C22	109.0 (2)	C20—C22—H22C	109.5
C23—C20—C12	112.25 (16)	H22A—C22—H22C	109.5
C22—C20—C12	109.95 (17)	H22B—C22—H22C	109.5
C23—C20—C21	107.9 (2)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O7B—H7B···N4^i	0.82	2.49	3.198 (7)	146
C2—H2···O19^ii	0.93	2.54	3.365 (3)	147
C23—H23B···O19^iii	0.96	2.59	3.421 (3)	146
C22—H22B···Cg3^iv	0.96	2.99	3.818 (3)	145

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