4-[(4-Hy­droxy­methyl-2H-1,2,3-triazol-2-yl)meth­yl]-6-isopropyl-2H-chromen-2-one

El-Khatatneh, N.; Chandra; Shamala, D.; Shivashankar, K.; Mahendra, M.

doi:10.1107/S2414314616019891

4-[(4-Hydroxymethyl-2H-1,2,3-triazol-2-yl)methyl]-6-isopropyl-2H-chromen-2-one

N. El-Khatatneh, Chandra, D. Shamala, K. Shivashankar and M. Mahendra

In the title compound, C₁₆H₁₇N₃O₃, the chromene ring is planar, with a maximum deviation of 0.017 (4) Å for the ring O atom. The triazole and the chromene rings, bridged by a methylene C atom, are inclined to one another by 78.3 (2)°. In the crystal, methylene–triazole C—H

N hydrogen bonds lead to the formation of helical supramolecular chains along the b axis. The sample was refined as an inversion twin. The terminal methylhydroxy group is disordered over two sets of sites [site occupancy = 0.610 (13) for the major component].

Keywords: crystal structure; chromones; triazole; conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616019891/tk4026sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314616019891/tk4026Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616019891/tk4026Isup3.cml Supplementary material

CCDC reference: 1523344

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.058
wR factor = 0.173
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor      >O1A    -- >H1A    ...     Please Check

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.400
           From the CIF: _refine_ls_abs_structure_Flack_su    0.600
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.80 Note
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     --  C3      ..        5.5 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     --  C7      ..        6.0 s.u.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         N4 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C13 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00671 Ang.
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C2AA
                    C2AA   O1A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C2AA
                    C2AA   C3
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C2AA
                    C2AA   H2A1
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C2AA
                    C2AA   H2A2
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       O1AA
                    O1AA   H1A
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C2BB
                    C2BB   O1B
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C2BB
                    C2BB   C3
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C2BB
                    C2BB   H2B1
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       C2BB
                    C2BB   H2B2
PLAT711_ALERT_1_C BOND    Unknown or Inconsistent Label ..........       O1BB
                    O1BB   H1B
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       O1AA
                    O1AA   C2AA   C3
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       O1AA
                    O1AA   C2AA   H2A1
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C2AA
                    C3     C2AA   H2A1
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       O1AA
                    O1AA   C2AA   H2A2
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C2AA
                    C3     C2AA   H2A2
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H2A1A
                    H2A1A  C2AA   H2A2
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C2AA
                    C2AA   O1AA   H1A
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       O1BB
                    O1BB   C2BB   C3
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       O1BB
                    O1BB   C2BB   H2B1
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C2BB
                    C3     C2BB   H2B1
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       O1BB
                    O1BB   C2BB   H2B2
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C2BB
                    C3     C2BB   H2B2
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........      H2B1B
                    H2B1B  C2BB   H2B2
PLAT712_ALERT_1_C ANGLE   Unknown or Inconsistent Label ..........       C2BB
                    C2BB   O1BB   H1B
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 .      0.600 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.11 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          2 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)        273 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        273 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..          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          61 % Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.36 Check

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

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

4-[(4-Hydroxymethyl-2H-1,2,3-triazol-2-yl)methyl]-6-isopropyl-2H-chromen-2-one top

Crystal data top

C₁₆H₁₇N₃O₃	F(000) = 316
M_r = 299.32	D_x = 1.315 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.715 (5) Å	Cell parameters from 2680 reflections
b = 7.301 (4) Å	θ = 1.7–25.0°
c = 12.113 (6) Å	µ = 0.09 mm⁻¹
β = 101.209 (9)°	T = 273 K
V = 756.0 (7) Å³	Block, colourless
Z = 2	0.35 × 0.25 × 0.15 mm

Data collection top

Bruker MicroStar microfocus rotating anode diffractometer	R_int = 0.026
Detector resolution: 18.4 pixels mm^-1	θ_max = 25.0°, θ_min = 1.7°
φ and ω scans	h = −10→10
7069 measured reflections	k = −8→8
2680 independent reflections	l = −14→14
2307 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.173	w = 1/[σ²(F_o²) + (0.1139P)² + 0.0997P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2680 reflections	Δρ_max = 0.25 e Å⁻³
214 parameters	Δρ_min = −0.28 e Å⁻³
38 restraints	Absolute structure: Flack x determined using 884 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.4 (6)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C2A	0.432 (4)	−0.285 (8)	−0.109 (3)	0.080 (3)	0.610 (13)
H2A1	0.474773	−0.398344	−0.075005	0.096*	0.610 (13)
H2A2	0.399222	−0.304324	−0.189741	0.096*	0.610 (13)
O1A	0.5459 (9)	−0.1448 (13)	−0.0887 (7)	0.109 (4)	0.610 (13)
H1A	0.567622	−0.123296	−0.021052	0.164*	0.610 (13)
C2B	0.445 (6)	−0.277 (14)	−0.090 (6)	0.080 (3)	0.390 (13)
H2B1	0.430161	−0.396496	−0.126013	0.096*	0.390 (13)
H2B2	0.467401	−0.191108	−0.145752	0.096*	0.390 (13)
O1B	0.5778 (11)	−0.2871 (17)	−0.0017 (10)	0.089 (4)	0.390 (13)
H1B	0.560748	−0.359343	0.046267	0.133*	0.390 (13)
O19	0.0897 (4)	0.2890 (4)	0.3404 (2)	0.0600 (8)
C11	−0.1689 (4)	−0.1100 (6)	0.2962 (4)	0.0508 (10)
H11	−0.191640	−0.210542	0.248665	0.061*
C9	0.0411 (4)	−0.0058 (5)	0.1920 (3)	0.0446 (9)
C10	−0.0518 (5)	0.0111 (5)	0.2791 (3)	0.0453 (9)
C18	−0.0219 (5)	0.1603 (6)	0.3514 (4)	0.0509 (10)
C20	0.1754 (5)	0.2769 (6)	0.2573 (4)	0.0550 (11)
C22	0.1485 (5)	0.1217 (6)	0.1844 (3)	0.0488 (10)
H22	0.208492	0.108718	0.129199	0.059*
C17	−0.1015 (6)	0.1867 (7)	0.4379 (4)	0.0612 (12)
H17	−0.078051	0.286037	0.486358	0.073*
N5	0.1126 (4)	−0.1759 (5)	0.0339 (3)	0.0497 (8)
C12	−0.2519 (5)	−0.0858 (7)	0.3810 (4)	0.0562 (11)
C8	0.0117 (5)	−0.1697 (6)	0.1159 (4)	0.0576 (11)
H8A	0.027464	−0.279960	0.161356	0.069*
H8B	−0.096445	−0.168051	0.076627	0.069*
O21	0.2705 (4)	0.3975 (6)	0.2539 (3)	0.0804 (11)
C7	0.1952 (5)	−0.0965 (6)	−0.1125 (3)	0.0530 (10)
H7	0.204076	−0.038826	−0.179462	0.064*
N4	0.2440 (5)	−0.2750 (7)	0.0358 (4)	0.0734 (12)
C16	−0.2155 (6)	0.0646 (7)	0.4515 (4)	0.0642 (12)
H16	−0.269929	0.082688	0.509450	0.077*
N6	0.0842 (5)	−0.0676 (5)	−0.0562 (3)	0.0628 (10)
C3	0.2948 (6)	−0.2225 (7)	−0.0586 (4)	0.0636 (12)
C13	−0.3833 (5)	−0.2128 (8)	0.3976 (5)	0.0683 (13)
H13	−0.392494	−0.200590	0.476651	0.082*
C14	−0.3496 (9)	−0.4077 (10)	0.3806 (8)	0.121 (3)
H14A	−0.429774	−0.482233	0.401963	0.182*
H14B	−0.250109	−0.439262	0.425926	0.182*
H14C	−0.347001	−0.428504	0.302684	0.182*
C15	−0.5364 (6)	−0.1510 (13)	0.3291 (7)	0.120 (3)
H15A	−0.542993	−0.187489	0.252200	0.180*
H15B	−0.543668	−0.020020	0.333103	0.180*
H15C	−0.620528	−0.205715	0.358126	0.180*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2A	0.086 (6)	0.071 (6)	0.097 (12)	−0.005 (5)	0.050 (5)	−0.015 (11)
O1A	0.109 (6)	0.109 (7)	0.125 (7)	−0.029 (5)	0.063 (5)	−0.052 (5)
C2B	0.086 (6)	0.071 (6)	0.097 (12)	−0.005 (5)	0.050 (5)	−0.015 (11)
O1B	0.069 (6)	0.093 (8)	0.110 (8)	0.029 (6)	0.033 (6)	0.033 (6)
O19	0.0690 (18)	0.0526 (18)	0.0603 (17)	−0.0160 (15)	0.0173 (15)	−0.0159 (14)
C11	0.048 (2)	0.045 (2)	0.060 (2)	−0.0010 (19)	0.0126 (18)	0.0015 (19)
C9	0.047 (2)	0.0389 (19)	0.047 (2)	0.0028 (17)	0.0077 (16)	0.0007 (16)
C10	0.048 (2)	0.041 (2)	0.048 (2)	0.0023 (16)	0.0110 (16)	0.0018 (17)
C18	0.052 (2)	0.051 (2)	0.051 (2)	−0.0022 (19)	0.0131 (17)	0.0017 (19)
C20	0.053 (2)	0.055 (3)	0.058 (2)	−0.014 (2)	0.0144 (19)	−0.003 (2)
C22	0.052 (2)	0.048 (2)	0.049 (2)	−0.0036 (19)	0.0154 (17)	0.0005 (18)
C17	0.071 (3)	0.060 (3)	0.055 (2)	0.002 (2)	0.019 (2)	−0.006 (2)
N5	0.0589 (19)	0.0377 (17)	0.0539 (19)	0.0035 (16)	0.0139 (15)	−0.0042 (15)
C12	0.049 (2)	0.059 (3)	0.063 (2)	0.007 (2)	0.0184 (18)	0.015 (2)
C8	0.066 (2)	0.046 (2)	0.067 (3)	−0.011 (2)	0.028 (2)	−0.009 (2)
O21	0.083 (2)	0.073 (2)	0.092 (2)	−0.039 (2)	0.0307 (19)	−0.023 (2)
C7	0.080 (3)	0.039 (2)	0.045 (2)	0.001 (2)	0.0247 (19)	0.0076 (18)
N4	0.080 (3)	0.059 (3)	0.084 (3)	0.003 (2)	0.023 (2)	−0.008 (2)
C16	0.065 (3)	0.068 (3)	0.065 (3)	0.011 (2)	0.027 (2)	0.006 (2)
N6	0.077 (2)	0.048 (2)	0.066 (2)	0.0081 (19)	0.0191 (18)	0.0050 (18)
C3	0.070 (3)	0.055 (3)	0.072 (3)	−0.006 (2)	0.030 (2)	−0.009 (2)
C13	0.058 (3)	0.071 (3)	0.080 (3)	−0.002 (2)	0.024 (2)	0.015 (3)
C14	0.119 (6)	0.065 (4)	0.199 (8)	−0.025 (4)	0.079 (6)	0.000 (5)
C15	0.063 (3)	0.134 (7)	0.153 (7)	−0.020 (4)	−0.002 (4)	0.047 (6)

Geometric parameters (Å, º) top

C2Aa—O1A	1.41 (4)	C17—C16	1.368 (7)
C2Aa—C3	1.52 (5)	C17—H17	0.9300
C2Aa—H2A1	0.9700	N5—N6	1.331 (5)
C2Aa—H2A2	0.9700	N5—N4	1.351 (5)
O1Aa—H1A	0.8200	N5—C8	1.450 (5)
C2Bb—O1B	1.42 (4)	C12—C16	1.389 (7)
C2Bb—C3	1.49 (8)	C12—C13	1.517 (6)
C2Bb—H2B1	0.9700	C8—H8A	0.9700
C2Bb—H2B2	0.9700	C8—H8B	0.9700
O1Bb—H1B	0.8200	C7—N6	1.305 (6)
O19—C20	1.368 (5)	C7—C3	1.343 (7)
O19—C18	1.377 (5)	C7—H7	0.9300
C11—C12	1.378 (6)	N4—C3	1.359 (7)
C11—C10	1.396 (5)	C16—H16	0.9300
C11—H11	0.9300	C13—C14	1.476 (10)
C9—C22	1.335 (6)	C13—C15	1.497 (8)
C9—C10	1.454 (5)	C13—H13	0.9800
C9—C8	1.502 (6)	C14—H14A	0.9600
C10—C18	1.390 (6)	C14—H14B	0.9600
C18—C17	1.378 (6)	C14—H14C	0.9600
C20—O21	1.215 (5)	C15—H15A	0.9600
C20—C22	1.428 (6)	C15—H15B	0.9600
C22—H22	0.9300	C15—H15C	0.9600

O1Aa—C2Aa—C3	107 (4)	C11—C12—C13	122.7 (5)
O1Aa—C2Aa—H2A1	110.3	C16—C12—C13	119.3 (4)
C3—C2Aa—H2A1	110.3	N5—C8—C9	113.1 (3)
O1Aa—C2Aa—H2A2	110.3	N5—C8—H8A	109.0
C3—C2Aa—H2A2	110.3	C9—C8—H8A	109.0
H2A1a—C2Aa—H2A2	108.5	N5—C8—H8B	109.0
C2Aa—O1Aa—H1A	109.5	C9—C8—H8B	109.0
O1Bb—C2Bb—C3	117 (5)	H8A—C8—H8B	107.8
O1Bb—C2Bb—H2B1	108.1	N6—C7—C3	109.3 (4)
C3—C2Bb—H2B1	108.1	N6—C7—H7	125.3
O1Bb—C2Bb—H2B2	108.1	C3—C7—H7	125.3
C3—C2Bb—H2B2	108.1	N5—N4—C3	104.4 (4)
H2B1b—C2Bb—H2B2	107.3	C17—C16—C12	121.7 (4)
C2Bb—O1Bb—H1B	109.5	C17—C16—H16	119.1
C20—O19—C18	121.6 (3)	C12—C16—H16	119.1
C12—C11—C10	122.3 (4)	C7—N6—N5	107.1 (4)
C12—C11—H11	118.9	C7—C3—N4	108.5 (4)
C10—C11—H11	118.9	C7—C3—C2B	125 (3)
C22—C9—C10	119.2 (4)	N4—C3—C2B	126 (3)
C22—C9—C8	123.5 (4)	C7—C3—C2A	120 (2)
C10—C9—C8	117.4 (3)	N4—C3—C2A	132 (2)
C18—C10—C11	117.1 (4)	C14—C13—C15	113.2 (7)
C18—C10—C9	117.5 (4)	C14—C13—C12	113.3 (5)
C11—C10—C9	125.5 (4)	C15—C13—C12	110.9 (5)
O19—C18—C17	116.6 (4)	C14—C13—H13	106.3
O19—C18—C10	121.5 (4)	C15—C13—H13	106.3
C17—C18—C10	121.9 (4)	C12—C13—H13	106.3
O21—C20—O19	116.8 (4)	C13—C14—H14A	109.5
O21—C20—C22	125.8 (4)	C13—C14—H14B	109.5
O19—C20—C22	117.3 (3)	H14A—C14—H14B	109.5
C9—C22—C20	122.9 (4)	C13—C14—H14C	109.5
C9—C22—H22	118.5	H14A—C14—H14C	109.5
C20—C22—H22	118.5	H14B—C14—H14C	109.5
C16—C17—C18	119.0 (5)	C13—C15—H15A	109.5
C16—C17—H17	120.5	C13—C15—H15B	109.5
C18—C17—H17	120.5	H15A—C15—H15B	109.5
N6—N5—N4	110.7 (4)	C13—C15—H15C	109.5
N6—N5—C8	120.1 (3)	H15A—C15—H15C	109.5
N4—N5—C8	129.1 (4)	H15B—C15—H15C	109.5
C11—C12—C16	118.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N6ⁱ	0.97	2.55	3.070 (6)	114

Symmetry code: (i) −x, y−1/2, −z.

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4-[(4-Hy­droxy­methyl-2H-1,2,3-triazol-2-yl)meth­yl]-6-isopropyl-2H-chromen-2-one

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4-[(4-Hydroxymethyl-2H-1,2,3-triazol-2-yl)methyl]-6-isopropyl-2H-chromen-2-one