6-Hexyl-7-hydroxy-3-(3-phenyl-1H-1,2,4-triazol-5-yl)-2H-chromen-2-one monohydrate

On heating N′-benzoyl-7-hydroxy-6-hexyl-2-oxo-2H-chromene-3-carbohydrazon­amide in di­methyl­form­amide, the process of cyclization leads to the formation of a triazole derivative of a 3-substituted chromenone, C₂₃H₂₃N₃O₃·H₂O, as confirmed by this crystal structure investigation. The three ring systems are almost coplanar and, in the crystal structure, a three-dimensional network of hydrogen bonds is formed; these are of the types O—H...O, N—H...N, O—H...N and C—H...O.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.099
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O1     -   C2      ..       7.35 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O2     -   C2      ..      12.36 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O3     -   C8      ..      10.60 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N1     -   C12     ..      10.70 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N2     -   C11     ..      10.62 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    N3     -   C12     ..       8.03 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C13    -   C14     ..      12.80 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C13    -   C18     ..      15.08 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C14    -   C15     ..       8.28 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C15    -   C16     ..      12.48 su

Alert level C
PLAT126_ALERT_1_C Error in or Uninterpretable Hall Symbol  .......       -1 P
PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Expl ....       -1 p
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.28 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.70 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.10 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     -   C19     ..       5.12 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C9      ..       5.27 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       6.23 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C19    -   C20     ..       6.51 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

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

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

---

Computing details

Data collection: P3 (Siemens,1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991) and XPREP (Siemens, 1991); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

C23H23N3O3·H2O	Z = 2
Mr = 407.46	F(000) = 432
Triclinic, P1	Dx = 1.252 Mg m^−3
Hall symbol: -1 P	Mo Kα radiation, λ = 0.71073 Å
a = 9.465 (2) Å	Cell parameters from 24 reflections
b = 10.316 (2) Å	θ = 11.0–12.0°
c = 12.518 (3) Å	µ = 0.09 mm^−1
α = 79.521 (17)°	T = 293 K
β = 88.450 (17)°	Block, light yellow
γ = 64.259 (17)°	0.45 × 0.2 × 0.15 mm
V = 1080.7 (4) Å^3

Data collection

Siemens P3/PC diffractometer	θmax = 25.5°, θmin = 2.8°
2θ/θ scans	h = −10→11
4168 measured reflections	k = −10→12
3991 independent reflections	l = 0→14
2430 reflections with I > 2σ(I)	2 standard reflections every 98 reflections
Rint = 0.073	intensity decay: 1%

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0345P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.099	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.13 e Å^−3
3991 reflections	Δρmin = −0.13 e Å^−3
272 parameters

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.

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

	x	y	z	Uiso*/Ueq
O1	−0.07997 (10)	0.75071 (10)	0.42661 (8)	0.0486 (3)
O2	−0.27383 (11)	0.70592 (11)	0.49664 (9)	0.0613 (3)
O3	0.32411 (11)	0.87554 (11)	0.28299 (10)	0.0723 (3)
H3	0.2655	0.969	0.2945	0.087*
N1	−0.17197 (12)	0.35116 (12)	0.33385 (10)	0.0479 (3)
N2	−0.33907 (12)	0.49022 (12)	0.43667 (10)	0.0493 (3)
H2	−0.3821	0.5581	0.4743	0.059*
N3	−0.39466 (12)	0.39132 (13)	0.42375 (10)	0.0501 (3)
C2	−0.16616 (15)	0.67153 (15)	0.43574 (12)	0.0487 (4)
C3	−0.11732 (15)	0.55305 (15)	0.37428 (11)	0.0454 (4)
C4	0.00869 (15)	0.52392 (15)	0.31310 (12)	0.0479 (4)
H4	0.0384	0.4481	0.2745	0.058*
C5	0.09704 (15)	0.60629 (15)	0.30632 (12)	0.0465 (4)
C6	0.23119 (16)	0.58224 (16)	0.24616 (13)	0.0553 (4)
H6	0.268	0.5044	0.2091	0.066*
C7	0.31121 (16)	0.66795 (16)	0.23918 (12)	0.0515 (4)
C8	0.24939 (16)	0.78788 (16)	0.29472 (12)	0.0512 (4)
C9	0.12005 (15)	0.81336 (15)	0.35696 (12)	0.0475 (4)
H9	0.0832	0.8904	0.3948	0.057*
C10	0.04711 (14)	0.72305 (14)	0.36188 (11)	0.0429 (4)
C11	−0.20813 (15)	0.46701 (15)	0.38265 (12)	0.0451 (4)
C12	−0.28923 (15)	0.31064 (15)	0.36096 (11)	0.0442 (4)
C13	−0.30498 (15)	0.19117 (15)	0.32083 (12)	0.0465 (4)
C14	−0.41359 (18)	0.14165 (18)	0.36463 (16)	0.0684 (5)
H14	−0.4728	0.1808	0.4212	0.082*
C15	−0.4337 (2)	0.0324 (2)	0.32320 (18)	0.0840 (6)
H15	−0.505	−0.0022	0.3526	0.101*
C16	−0.3465 (2)	−0.0223 (2)	0.23880 (15)	0.0750 (5)
H16	−0.3629	−0.0917	0.2095	0.09*
C17	−0.2374 (2)	0.02122 (19)	0.19664 (15)	0.0719 (5)
H17	−0.1771	−0.02	0.1411	0.086*
C18	−0.21703 (19)	0.12949 (18)	0.23839 (14)	0.0646 (5)
H18	−0.1426	0.1603	0.2098	0.077*
C19	0.45558 (17)	0.63683 (17)	0.17444 (13)	0.0603 (5)
H19A	0.5096	0.5325	0.1745	0.09*
H19B	0.5264	0.664	0.2092	0.09*
C20	0.4156 (2)	0.7199 (2)	0.05761 (15)	0.0748 (6)
H20A	0.3702	0.8243	0.0575	0.112*
H20B	0.3372	0.6998	0.0251	0.112*
C21	0.5617 (2)	0.6779 (2)	−0.01296 (16)	0.0785 (6)
H21A	0.6171	0.572	−0.0026	0.118*
H21B	0.5259	0.7148	−0.0891	0.118*
C22	0.6752 (2)	0.7371 (2)	0.01348 (17)	0.0898 (6)
H22A	0.7179	0.6943	0.0879	0.135*
H22B	0.6186	0.8423	0.0082	0.135*
C23	0.8102 (2)	0.7038 (3)	−0.06264 (19)	0.1041 (7)
H23A	0.8669	0.5984	−0.0568	0.156*
H23B	0.767	0.7455	−0.137	0.156*
C24	0.9241 (3)	0.7630 (3)	−0.0388 (2)	0.1404 (10)
H24A	0.8789	0.8667	−0.0661	0.211*
H24B	1.02	0.7157	−0.0735	0.211*
H24C	0.9459	0.7442	0.0384	0.211*
O4	0.16083 (13)	1.12383 (13)	0.36105 (11)	0.0876 (4)
H4A	0.0619	1.1902	0.3427	0.105*
H4B	0.2018	1.1718	0.3913	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0463 (5)	0.0535 (5)	0.0567 (6)	−0.0284 (4)	0.0187 (4)	−0.0207 (4)
O2	0.0554 (5)	0.0688 (6)	0.0715 (7)	−0.0338 (5)	0.0330 (5)	−0.0281 (5)
O3	0.0672 (5)	0.0682 (6)	0.1109 (9)	−0.0485 (5)	0.0341 (6)	−0.0422 (6)
N1	0.0408 (5)	0.0598 (7)	0.0537 (7)	−0.0299 (5)	0.0133 (5)	−0.0170 (5)
N2	0.0421 (5)	0.0546 (6)	0.0611 (7)	−0.0266 (5)	0.0194 (5)	−0.0223 (5)
N3	0.0465 (5)	0.0558 (6)	0.0600 (8)	−0.0324 (5)	0.0115 (5)	−0.0143 (5)
C2	0.0445 (7)	0.0506 (8)	0.0520 (9)	−0.0219 (6)	0.0065 (7)	−0.0094 (7)
C3	0.0429 (7)	0.0497 (7)	0.0474 (8)	−0.0230 (6)	0.0064 (6)	−0.0115 (6)
C4	0.0502 (7)	0.0496 (8)	0.0489 (8)	−0.0250 (6)	0.0085 (6)	−0.0134 (6)
C5	0.0477 (7)	0.0475 (7)	0.0483 (8)	−0.0239 (6)	0.0069 (6)	−0.0108 (6)
C6	0.0538 (8)	0.0544 (8)	0.0628 (10)	−0.0254 (7)	0.0126 (7)	−0.0198 (7)
C7	0.0489 (7)	0.0532 (8)	0.0534 (9)	−0.0232 (6)	0.0083 (7)	−0.0114 (7)
C8	0.0489 (7)	0.0520 (8)	0.0566 (9)	−0.0254 (6)	0.0046 (7)	−0.0112 (7)
C9	0.0481 (7)	0.0504 (8)	0.0477 (8)	−0.0231 (6)	0.0075 (6)	−0.0146 (6)
C10	0.0402 (6)	0.0434 (7)	0.0468 (8)	−0.0196 (6)	0.0071 (6)	−0.0099 (6)
C11	0.0420 (7)	0.0480 (7)	0.0475 (8)	−0.0216 (6)	0.0047 (6)	−0.0091 (6)
C12	0.0407 (7)	0.0469 (7)	0.0443 (8)	−0.0188 (6)	0.0041 (6)	−0.0079 (6)
C13	0.0444 (7)	0.0502 (8)	0.0478 (8)	−0.0234 (6)	0.0071 (6)	−0.0095 (6)
C14	0.0612 (9)	0.0641 (9)	0.0886 (13)	−0.0322 (8)	0.0149 (9)	−0.0244 (9)
C15	0.0694 (10)	0.0734 (11)	0.1172 (17)	−0.0379 (9)	0.0037 (11)	−0.0193 (11)
C16	0.0816 (11)	0.0728 (11)	0.0764 (13)	−0.0365 (9)	−0.0042 (10)	−0.0194 (9)
C17	0.0804 (11)	0.0699 (10)	0.0695 (12)	−0.0343 (9)	0.0070 (9)	−0.0193 (9)
C18	0.0689 (9)	0.0651 (10)	0.0642 (11)	−0.0320 (8)	0.0033 (8)	−0.0156 (8)
C19	0.0569 (8)	0.0637 (9)	0.0637 (10)	−0.0297 (7)	0.0108 (8)	−0.0122 (8)
C20	0.0696 (10)	0.0776 (11)	0.0738 (12)	−0.0302 (9)	0.0078 (9)	−0.0122 (9)
C21	0.0764 (11)	0.0823 (12)	0.0805 (13)	−0.0367 (9)	0.0188 (10)	−0.0208 (10)
C22	0.0894 (12)	0.1020 (14)	0.0900 (14)	−0.0487 (11)	0.0253 (11)	−0.0313 (11)
C23	0.0942 (13)	0.1340 (17)	0.0971 (16)	−0.0584 (12)	0.0281 (12)	−0.0336 (13)
C24	0.1285 (18)	0.167 (2)	0.162 (3)	−0.0894 (16)	0.0384 (17)	−0.0567 (19)
O4	0.0608 (7)	0.0885 (7)	0.1263 (10)	−0.0267 (6)	0.0109 (7)	−0.0673 (7)

Geometric parameters (Å, º)

O1—C2	1.3730 (17)	C14—H14	0.93
O1—C10	1.3849 (15)	C15—C16	1.371 (3)
O2—C2	1.2198 (16)	C15—H15	0.93
O3—C8	1.3569 (18)	C16—C17	1.355 (3)
O3—H3	0.9168	C16—H16	0.93
N1—C11	1.3481 (18)	C17—C18	1.401 (2)
N1—C12	1.3612 (17)	C17—H17	0.93
N2—C11	1.3440 (16)	C18—H18	0.93
N2—N3	1.3692 (17)	C19—C20	1.520 (2)
N2—H2	0.86	C19—H19A	0.97
N3—C12	1.3343 (17)	C19—H19B	0.97
C2—C3	1.460 (2)	C20—C21	1.560 (2)
C3—C4	1.3500 (18)	C20—H20A	0.97
C3—C11	1.470 (2)	C20—H20B	0.97
C4—C5	1.420 (2)	C21—C22	1.516 (3)
C4—H4	0.93	C21—H21A	0.97
C5—C10	1.397 (2)	C21—H21B	0.97
C5—C6	1.4083 (19)	C22—C23	1.527 (3)
C6—C7	1.383 (2)	C22—H22A	0.97
C6—H6	0.93	C22—H22B	0.97
C7—C8	1.421 (2)	C23—C24	1.510 (3)
C7—C19	1.510 (2)	C23—H23A	0.97
C8—C9	1.3849 (19)	C23—H23B	0.97
C9—C10	1.373 (2)	C24—H24A	0.96
C9—H9	0.93	C24—H24B	0.96
C12—C13	1.477 (2)	C24—H24C	0.96
C13—C18	1.377 (2)	O4—H4A	0.8918
C13—C14	1.394 (2)	O4—H4B	0.8846
C14—C15	1.408 (3)
C2—O1—C10	122.81 (11)	C14—C15—H15	120.6
C8—O3—H3	115.7	C17—C16—C15	122.25 (19)
C11—N1—C12	103.24 (11)	C17—C16—H16	118.9
C11—N2—N3	110.89 (12)	C15—C16—H16	118.9
C11—N2—H2	124.6	C16—C17—C18	118.68 (17)
N3—N2—H2	124.6	C16—C17—H17	120.7
C12—N3—N2	101.89 (11)	C18—C17—H17	120.7
O2—C2—O1	116.17 (13)	C13—C18—C17	121.34 (16)
O2—C2—C3	126.82 (14)	C13—C18—H18	119.3
O1—C2—C3	116.99 (12)	C17—C18—H18	119.3
C4—C3—C2	120.23 (14)	C7—C19—C20	112.21 (13)
C4—C3—C11	121.84 (14)	C7—C19—H19A	109.2
C2—C3—C11	117.93 (12)	C20—C19—H19A	109.2
C3—C4—C5	121.60 (14)	C7—C19—H19B	109.2
C3—C4—H4	119.2	C20—C19—H19B	109.2
C5—C4—H4	119.2	H19A—C19—H19B	107.9
C10—C5—C6	116.27 (14)	C19—C20—C21	112.71 (14)
C10—C5—C4	118.23 (12)	C19—C20—H20A	109
C6—C5—C4	125.49 (14)	C21—C20—H20A	109
C7—C6—C5	123.62 (14)	C19—C20—H20B	109
C7—C6—H6	118.2	C21—C20—H20B	109
C5—C6—H6	118.2	H20A—C20—H20B	107.8
C6—C7—C8	116.60 (13)	C22—C21—C20	113.84 (17)
C6—C7—C19	121.65 (14)	C22—C21—H21A	108.8
C8—C7—C19	121.74 (14)	C20—C21—H21A	108.8
O3—C8—C9	122.21 (14)	C22—C21—H21B	108.8
O3—C8—C7	116.16 (13)	C20—C21—H21B	108.8
C9—C8—C7	121.63 (14)	H21A—C21—H21B	107.7
C10—C9—C8	118.91 (14)	C21—C22—C23	112.44 (18)
C10—C9—H9	120.5	C21—C22—H22A	109.1
C8—C9—H9	120.5	C23—C22—H22A	109.1
C9—C10—O1	117.05 (12)	C21—C22—H22B	109.1
C9—C10—C5	122.90 (12)	C23—C22—H22B	109.1
O1—C10—C5	120.05 (13)	H22A—C22—H22B	107.8
N2—C11—N1	109.06 (13)	C24—C23—C22	113.5 (2)
N2—C11—C3	126.95 (13)	C24—C23—H23A	108.9
N1—C11—C3	123.98 (12)	C22—C23—H23A	108.9
N3—C12—N1	114.92 (13)	C24—C23—H23B	108.9
N3—C12—C13	121.62 (12)	C22—C23—H23B	108.9
N1—C12—C13	123.40 (12)	H23A—C23—H23B	107.7
C18—C13—C14	118.78 (15)	C23—C24—H24A	109.5
C18—C13—C12	121.30 (14)	C23—C24—H24B	109.5
C14—C13—C12	119.89 (13)	H24A—C24—H24B	109.5
C13—C14—C15	119.99 (16)	C23—C24—H24C	109.5
C13—C14—H14	120	H24A—C24—H24C	109.5
C15—C14—H14	120	H24B—C24—H24C	109.5
C16—C15—C14	118.89 (18)	H4A—O4—H4B	103.4
C16—C15—H15	120.6
C11—N2—N3—C12	0.45 (14)	N3—N2—C11—C3	178.00 (13)
C10—O1—C2—O2	179.05 (12)	C12—N1—C11—N2	0.89 (14)
C10—O1—C2—C3	0.64 (18)	C12—N1—C11—C3	−178.03 (13)
O2—C2—C3—C4	−177.34 (14)	C4—C3—C11—N2	−176.68 (14)
O1—C2—C3—C4	0.88 (19)	C2—C3—C11—N2	4.1 (2)
O2—C2—C3—C11	1.9 (2)	C4—C3—C11—N1	2.1 (2)
O1—C2—C3—C11	−179.87 (11)	C2—C3—C11—N1	−177.19 (13)
C2—C3—C4—C5	0.0 (2)	N2—N3—C12—N1	0.14 (15)
C11—C3—C4—C5	−179.26 (13)	N2—N3—C12—C13	−177.24 (12)
C3—C4—C5—C10	−2.3 (2)	C11—N1—C12—N3	−0.65 (15)
C3—C4—C5—C6	178.92 (14)	C11—N1—C12—C13	176.68 (13)
C10—C5—C6—C7	−0.8 (2)	N3—C12—C13—C18	165.86 (14)
C4—C5—C6—C7	178.02 (14)	N1—C12—C13—C18	−11.3 (2)
C5—C6—C7—C8	−1.5 (2)	N3—C12—C13—C14	−12.4 (2)
C5—C6—C7—C19	179.40 (14)	N1—C12—C13—C14	170.45 (14)
C6—C7—C8—O3	−176.86 (13)	C18—C13—C14—C15	−1.1 (2)
C19—C7—C8—O3	2.3 (2)	C12—C13—C14—C15	177.18 (15)
C6—C7—C8—C9	3.0 (2)	C13—C14—C15—C16	−0.8 (3)
C19—C7—C8—C9	−177.85 (14)	C14—C15—C16—C17	2.6 (3)
O3—C8—C9—C10	177.68 (13)	C15—C16—C17—C18	−2.3 (3)
C7—C8—C9—C10	−2.2 (2)	C14—C13—C18—C17	1.5 (2)
C8—C9—C10—O1	178.85 (12)	C12—C13—C18—C17	−176.83 (14)
C8—C9—C10—C5	−0.3 (2)	C16—C17—C18—C13	0.2 (2)
C2—O1—C10—C9	177.84 (12)	C6—C7—C19—C20	91.41 (18)
C2—O1—C10—C5	−2.99 (18)	C8—C7—C19—C20	−87.68 (19)
C6—C5—C10—C9	1.8 (2)	C7—C19—C20—C21	−174.75 (15)
C4—C5—C10—C9	−177.16 (13)	C19—C20—C21—C22	−72.5 (2)
C6—C5—C10—O1	−177.35 (12)	C20—C21—C22—C23	−175.70 (16)
C4—C5—C10—O1	3.71 (19)	C21—C22—C23—C24	179.39 (18)
N3—N2—C11—N1	−0.88 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.92	1.81	2.701 (2)	162
N2—H2···O2	0.86	2.23	2.779 (2)	121
N2—H2···N3^i	0.86	2.35	2.960 (2)	129
O4—H4A···N1^ii	0.89	2.10	2.981 (2)	168
O4—H4B···O2^iii	0.89	2.34	3.206 (2)	167
C14—H14···O2^i	0.93	2.46	3.304 (2)	151

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