Crystal structure, Hirshfeld surface analysis and DFT studies of 1-benzyl-3-[(1-benzyl-1H-1,2,3-triazol-5-yl)meth­yl]-2,3-di­hydro-1H-1,3-benzo­diazol-2-one monohydrate

The di­hydro­benzo­diazole moiety is not quite planar while the whole mol­ecule adopts a U-shaped conformation in which there is a close approach of the two benzyl groups. Chains of alternating mol­ecules and lattice water extending along the normal to (301) are formed by O—H...O and O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.113
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.514 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         28 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         29 Note

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

   0 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016; program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

1-Benzyl-3-[(1-benzyl-1H-1,2,3-triazol-5-yl)methyl]-2,3-dihydro-1H-1,3-benzodiazol-2-one monohydrate

Crystal data

C24H21N5O·H2O	F(000) = 872
Mr = 413.47	Dx = 1.325 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 9.0872 (2) Å	Cell parameters from 9060 reflections
b = 21.1012 (4) Å	θ = 4.2–70.2°
c = 11.7134 (2) Å	µ = 0.70 mm^−1
β = 112.654 (1)°	T = 150 K
V = 2072.77 (7) Å^3	Plate, colourless
Z = 4	0.18 × 0.08 × 0.01 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3887 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2909 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.057
Detector resolution: 10.4167 pixels mm^-1	θmax = 70.2°, θmin = 4.2°
ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −24→25
Tmin = 0.85, Tmax = 0.99	l = −14→13
15080 measured reflections

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)] = 0.048	Hydrogen site location: mixed
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 0.901P] where P = (Fo^2 + 2Fc^2)/3
3887 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.21 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.

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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to oxygen were placed in locations derived from a difference map and their coordinates adjusted to give O—H = 0.87 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	Uiso*/Ueq
O1	0.85567 (15)	0.39779 (7)	0.93327 (13)	0.0375 (4)
N1	0.58475 (17)	0.39409 (7)	0.89638 (14)	0.0267 (3)
N2	0.68572 (18)	0.48484 (7)	0.86568 (14)	0.0278 (3)
N3	0.3094 (2)	0.22818 (9)	0.68794 (17)	0.0426 (5)
N4	0.4467 (2)	0.21861 (8)	0.67770 (16)	0.0378 (4)
N5	0.55663 (19)	0.25352 (8)	0.76599 (15)	0.0300 (4)
C1	0.5258 (2)	0.49606 (9)	0.84381 (16)	0.0274 (4)
C2	0.4364 (2)	0.55101 (10)	0.81370 (18)	0.0350 (5)
H2	0.480398	0.590041	0.801540	0.042*
C3	0.2785 (3)	0.54622 (11)	0.80211 (19)	0.0411 (5)
H3	0.213195	0.583008	0.781973	0.049*
C4	0.2141 (2)	0.48927 (12)	0.8192 (2)	0.0416 (5)
H4	0.105243	0.487817	0.808961	0.050*
C5	0.3051 (2)	0.43389 (11)	0.85099 (18)	0.0342 (5)
H5	0.261424	0.394902	0.863712	0.041*
C6	0.4618 (2)	0.43874 (9)	0.86300 (16)	0.0263 (4)
C7	0.7242 (2)	0.42276 (9)	0.90173 (17)	0.0275 (4)
C8	0.5772 (2)	0.32986 (9)	0.93828 (18)	0.0307 (4)
H8A	0.523147	0.330364	0.997257	0.037*
H8B	0.686995	0.313896	0.982830	0.037*
C9	0.4903 (2)	0.28571 (9)	0.83436 (17)	0.0288 (4)
C10	0.3330 (2)	0.26854 (10)	0.7837 (2)	0.0381 (5)
H10	0.252957	0.282630	0.811211	0.046*
C11	0.7188 (2)	0.25400 (10)	0.77111 (19)	0.0337 (5)
H11A	0.752881	0.209810	0.766704	0.040*
H11B	0.790188	0.271831	0.851613	0.040*
C12	0.7378 (2)	0.29187 (9)	0.66852 (17)	0.0303 (4)
C13	0.6180 (3)	0.32884 (10)	0.58683 (19)	0.0372 (5)
H13	0.516342	0.330255	0.592204	0.045*
C14	0.6458 (3)	0.36398 (11)	0.4968 (2)	0.0439 (5)
H14	0.562951	0.389101	0.440157	0.053*
C15	0.7931 (3)	0.36233 (12)	0.4897 (2)	0.0499 (6)
H15	0.813571	0.387548	0.430265	0.060*
C16	0.9119 (3)	0.32390 (14)	0.5694 (2)	0.0531 (7)
H16	1.012885	0.321923	0.563017	0.064*
C17	0.8840 (3)	0.28853 (12)	0.6578 (2)	0.0439 (6)
H17	0.965324	0.261779	0.711555	0.053*
C18	0.8011 (2)	0.53227 (10)	0.86554 (18)	0.0336 (5)
H18A	0.909556	0.515338	0.911413	0.040*
H18B	0.787800	0.570113	0.910627	0.040*
C19	0.7883 (2)	0.55247 (9)	0.73841 (17)	0.0280 (4)
C20	0.7223 (3)	0.51411 (11)	0.6354 (2)	0.0435 (5)
H20	0.679963	0.473924	0.643246	0.052*
C21	0.7171 (3)	0.53360 (12)	0.5208 (2)	0.0493 (6)
H21	0.671787	0.506684	0.450937	0.059*
C22	0.7773 (3)	0.59167 (12)	0.5081 (2)	0.0430 (5)
H22	0.772714	0.605182	0.429394	0.052*
C23	0.8446 (3)	0.63033 (11)	0.6103 (2)	0.0432 (5)
H23	0.886487	0.670536	0.602007	0.052*
C24	0.8509 (2)	0.61052 (10)	0.7246 (2)	0.0357 (5)
H24	0.898875	0.637078	0.794666	0.043*
O2	0.10404 (17)	0.18802 (8)	0.44186 (14)	0.0478 (4)
H2A	0.155922	0.195519	0.520249	0.072*
H2B	0.031707	0.160858	0.441258	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0242 (7)	0.0395 (9)	0.0441 (8)	0.0055 (6)	0.0078 (6)	−0.0002 (7)
N1	0.0247 (8)	0.0244 (8)	0.0286 (8)	0.0013 (6)	0.0077 (6)	−0.0006 (6)
N2	0.0259 (8)	0.0263 (9)	0.0283 (8)	−0.0016 (7)	0.0072 (6)	0.0013 (7)
N3	0.0363 (9)	0.0486 (12)	0.0454 (11)	−0.0144 (9)	0.0184 (8)	−0.0126 (9)
N4	0.0385 (9)	0.0358 (10)	0.0409 (10)	−0.0099 (8)	0.0174 (8)	−0.0081 (8)
N5	0.0306 (8)	0.0291 (9)	0.0316 (9)	−0.0037 (7)	0.0132 (7)	−0.0018 (7)
C1	0.0267 (9)	0.0319 (11)	0.0206 (9)	0.0029 (8)	0.0059 (7)	−0.0007 (7)
C2	0.0430 (11)	0.0328 (12)	0.0277 (10)	0.0085 (9)	0.0120 (9)	0.0036 (8)
C3	0.0438 (12)	0.0442 (14)	0.0339 (11)	0.0195 (10)	0.0134 (9)	0.0054 (9)
C4	0.0303 (10)	0.0591 (15)	0.0360 (12)	0.0118 (10)	0.0132 (9)	0.0009 (10)
C5	0.0302 (10)	0.0429 (13)	0.0311 (10)	0.0015 (9)	0.0135 (8)	−0.0007 (9)
C6	0.0255 (9)	0.0303 (11)	0.0215 (9)	0.0024 (8)	0.0071 (7)	−0.0011 (8)
C7	0.0232 (9)	0.0302 (10)	0.0252 (9)	−0.0006 (8)	0.0050 (7)	−0.0023 (8)
C8	0.0345 (10)	0.0279 (11)	0.0280 (10)	0.0011 (8)	0.0101 (8)	0.0026 (8)
C9	0.0309 (9)	0.0272 (10)	0.0297 (10)	−0.0018 (8)	0.0132 (8)	0.0019 (8)
C10	0.0350 (11)	0.0409 (13)	0.0416 (12)	−0.0073 (9)	0.0182 (9)	−0.0083 (10)
C11	0.0288 (10)	0.0375 (12)	0.0362 (11)	0.0025 (9)	0.0138 (8)	0.0018 (9)
C12	0.0303 (10)	0.0318 (11)	0.0283 (10)	−0.0052 (8)	0.0108 (8)	−0.0047 (8)
C13	0.0401 (11)	0.0333 (12)	0.0401 (12)	0.0026 (9)	0.0177 (9)	0.0022 (9)
C14	0.0584 (14)	0.0363 (13)	0.0350 (12)	0.0035 (11)	0.0159 (10)	0.0016 (9)
C15	0.0679 (16)	0.0510 (15)	0.0377 (13)	−0.0150 (13)	0.0279 (12)	−0.0003 (11)
C16	0.0404 (12)	0.0785 (19)	0.0447 (14)	−0.0136 (13)	0.0211 (11)	0.0002 (13)
C17	0.0313 (10)	0.0601 (16)	0.0386 (12)	−0.0021 (10)	0.0115 (9)	0.0025 (11)
C18	0.0328 (10)	0.0340 (11)	0.0296 (10)	−0.0092 (9)	0.0070 (8)	−0.0023 (9)
C19	0.0240 (9)	0.0285 (10)	0.0309 (10)	−0.0005 (8)	0.0099 (7)	−0.0008 (8)
C20	0.0551 (14)	0.0388 (13)	0.0352 (12)	−0.0153 (11)	0.0159 (10)	−0.0061 (10)
C21	0.0625 (15)	0.0503 (15)	0.0340 (12)	−0.0167 (12)	0.0173 (11)	−0.0101 (11)
C22	0.0454 (12)	0.0512 (15)	0.0351 (12)	−0.0047 (11)	0.0188 (10)	0.0023 (10)
C23	0.0494 (13)	0.0384 (13)	0.0491 (13)	−0.0075 (10)	0.0272 (11)	0.0008 (10)
C24	0.0376 (11)	0.0323 (11)	0.0393 (12)	−0.0052 (9)	0.0171 (9)	−0.0062 (9)
O2	0.0397 (8)	0.0618 (11)	0.0395 (9)	−0.0154 (8)	0.0128 (7)	0.0018 (8)

Geometric parameters (Å, º)

O1—C7	1.225 (2)	C11—H11B	0.9900
N1—C7	1.384 (2)	C12—C13	1.381 (3)
N1—C6	1.397 (2)	C12—C17	1.384 (3)
N1—C8	1.452 (2)	C13—C14	1.390 (3)
N2—C7	1.379 (2)	C13—H13	0.9500
N2—C1	1.395 (2)	C14—C15	1.373 (3)
N2—C18	1.450 (2)	C14—H14	0.9500
N3—N4	1.314 (2)	C15—C16	1.385 (4)
N3—C10	1.358 (3)	C15—H15	0.9500
N4—N5	1.347 (2)	C16—C17	1.377 (3)
N5—C9	1.356 (2)	C16—H16	0.9500
N5—C11	1.452 (2)	C17—H17	0.9500
C1—C2	1.381 (3)	C18—C19	1.510 (3)
C1—C6	1.397 (3)	C18—H18A	0.9900
C2—C3	1.392 (3)	C18—H18B	0.9900
C2—H2	0.9500	C19—C20	1.383 (3)
C3—C4	1.384 (3)	C19—C24	1.386 (3)
C3—H3	0.9500	C20—C21	1.387 (3)
C4—C5	1.397 (3)	C20—H20	0.9500
C4—H4	0.9500	C21—C22	1.373 (3)
C5—C6	1.379 (3)	C21—H21	0.9500
C5—H5	0.9500	C22—C23	1.382 (3)
C8—C9	1.494 (3)	C22—H22	0.9500
C8—H8A	0.9900	C23—C24	1.383 (3)
C8—H8B	0.9900	C23—H23	0.9500
C9—C10	1.368 (3)	C24—H24	0.9500
C10—H10	0.9500	O2—H2A	0.8700
C11—C12	1.507 (3)	O2—H2B	0.8701
C11—H11A	0.9900
O2···O1^i	2.865 (2)	C10···H5	2.98
O2···C17^i	3.192 (3)	C11···H8B	2.90
O2···N3	2.892 (2)	C14···H20	2.83
O1···H8B	2.55	C18···H2	2.98
O1···H11B	2.81	C22···H16^vii	2.98
O1···H18A	2.56	C22···H13^vi	2.97
O1···H18A^ii	2.87	C23···H16^vii	2.97
O2···H5^iii	2.64	H2···N4^viii	2.78
O2···H11B^i	2.77	H2A···N4	2.62
O2···H17^i	2.71	H2A···N3	2.04
N4···C13	3.200 (3)	H2B···O1^i	2.00
N2···H20	2.60	H2B···H11B^i	2.48
N4···H13	2.73	H3···H15^vi	2.48
N5···H13	2.52	H4···H18A^ix	2.57
C1···C20	3.557 (3)	H5···H10	2.44
C2···C6^iv	3.542 (3)	H8A···N4^v	2.67
C3···C7^iv	3.540 (3)	H8B···H11B	2.27
C5···C9	3.592 (3)	H10···O2^v	2.48
C9···C5	3.592 (3)	H10···H17^ix	2.46
C10···O2^v	3.402 (3)	H11A···C15^v	2.92
C11···C15^v	3.421 (3)	H11A···H17	2.51
C14···C20	3.505 (3)	H16···H23^vii	2.44
C2···H18B	2.98	H16···H22^vii	2.46
C3···H15^vi	2.88	H18A···H18A^ii	2.19
C8···H11B	2.79	H18B···H24	2.43
C8···H5	2.99	H24···N3^viii	2.76
C7—N1—C6	109.72 (15)	N5—C11—H11B	108.9
C7—N1—C8	123.68 (15)	C12—C11—H11B	108.9
C6—N1—C8	125.96 (15)	H11A—C11—H11B	107.7
C7—N2—C1	109.90 (15)	C13—C12—C17	119.63 (19)
C7—N2—C18	123.91 (16)	C13—C12—C11	123.39 (18)
C1—N2—C18	125.82 (16)	C17—C12—C11	116.99 (18)
N4—N3—C10	108.55 (17)	C12—C13—C14	120.1 (2)
N3—N4—N5	107.17 (16)	C12—C13—H13	119.9
N4—N5—C9	111.14 (15)	C14—C13—H13	119.9
N4—N5—C11	118.44 (16)	C15—C14—C13	119.9 (2)
C9—N5—C11	130.35 (17)	C15—C14—H14	120.1
C2—C1—N2	131.12 (19)	C13—C14—H14	120.1
C2—C1—C6	121.84 (18)	C14—C15—C16	120.0 (2)
N2—C1—C6	106.99 (16)	C14—C15—H15	120.0
C1—C2—C3	116.5 (2)	C16—C15—H15	120.0
C1—C2—H2	121.7	C17—C16—C15	120.2 (2)
C3—C2—H2	121.7	C17—C16—H16	119.9
C4—C3—C2	121.7 (2)	C15—C16—H16	119.9
C4—C3—H3	119.1	C16—C17—C12	120.1 (2)
C2—C3—H3	119.1	C16—C17—H17	119.9
C3—C4—C5	121.65 (19)	C12—C17—H17	119.9
C3—C4—H4	119.2	N2—C18—C19	114.52 (15)
C5—C4—H4	119.2	N2—C18—H18A	108.6
C6—C5—C4	116.6 (2)	C19—C18—H18A	108.6
C6—C5—H5	121.7	N2—C18—H18B	108.6
C4—C5—H5	121.7	C19—C18—H18B	108.6
C5—C6—C1	121.66 (18)	H18A—C18—H18B	107.6
C5—C6—N1	131.39 (18)	C20—C19—C24	118.34 (19)
C1—C6—N1	106.93 (15)	C20—C19—C18	122.54 (18)
O1—C7—N2	127.11 (18)	C24—C19—C18	119.06 (17)
O1—C7—N1	126.52 (18)	C19—C20—C21	120.8 (2)
N2—C7—N1	106.37 (15)	C19—C20—H20	119.6
N1—C8—C9	112.68 (15)	C21—C20—H20	119.6
N1—C8—H8A	109.1	C22—C21—C20	120.2 (2)
C9—C8—H8A	109.1	C22—C21—H21	119.9
N1—C8—H8B	109.1	C20—C21—H21	119.9
C9—C8—H8B	109.1	C21—C22—C23	119.6 (2)
H8A—C8—H8B	107.8	C21—C22—H22	120.2
N5—C9—C10	103.82 (17)	C23—C22—H22	120.2
N5—C9—C8	125.29 (17)	C22—C23—C24	120.0 (2)
C10—C9—C8	130.88 (18)	C22—C23—H23	120.0
N3—C10—C9	109.31 (18)	C24—C23—H23	120.0
N3—C10—H10	125.3	C23—C24—C19	121.0 (2)
C9—C10—H10	125.3	C23—C24—H24	119.5
N5—C11—C12	113.37 (16)	C19—C24—H24	119.5
N5—C11—H11A	108.9	H2A—O2—H2B	103.2
C12—C11—H11A	108.9
C10—N3—N4—N5	−0.7 (2)	C11—N5—C9—C10	177.1 (2)
N3—N4—N5—C9	0.3 (2)	N4—N5—C9—C8	−178.77 (17)
N3—N4—N5—C11	−176.95 (17)	C11—N5—C9—C8	−1.9 (3)
C7—N2—C1—C2	175.59 (19)	N1—C8—C9—N5	86.6 (2)
C18—N2—C1—C2	2.4 (3)	N1—C8—C9—C10	−92.1 (3)
C7—N2—C1—C6	−1.9 (2)	N4—N3—C10—C9	0.9 (3)
C18—N2—C1—C6	−175.07 (17)	N5—C9—C10—N3	−0.7 (2)
N2—C1—C2—C3	−177.86 (19)	C8—C9—C10—N3	178.24 (19)
C6—C1—C2—C3	−0.7 (3)	N4—N5—C11—C12	73.3 (2)
C1—C2—C3—C4	−0.4 (3)	C9—N5—C11—C12	−103.4 (2)
C2—C3—C4—C5	1.1 (3)	N5—C11—C12—C13	7.5 (3)
C3—C4—C5—C6	−0.8 (3)	N5—C11—C12—C17	−172.44 (19)
C4—C5—C6—C1	−0.2 (3)	C17—C12—C13—C14	−1.9 (3)
C4—C5—C6—N1	178.04 (18)	C11—C12—C13—C14	178.1 (2)
C2—C1—C6—C5	1.0 (3)	C12—C13—C14—C15	−0.6 (3)
N2—C1—C6—C5	178.79 (17)	C13—C14—C15—C16	2.4 (4)
C2—C1—C6—N1	−177.65 (17)	C14—C15—C16—C17	−1.7 (4)
N2—C1—C6—N1	0.13 (19)	C15—C16—C17—C12	−0.8 (4)
C7—N1—C6—C5	−176.8 (2)	C13—C12—C17—C16	2.6 (3)
C8—N1—C6—C5	−5.8 (3)	C11—C12—C17—C16	−177.4 (2)
C7—N1—C6—C1	1.7 (2)	C7—N2—C18—C19	109.6 (2)
C8—N1—C6—C1	172.72 (16)	C1—N2—C18—C19	−78.2 (2)
C1—N2—C7—O1	−176.56 (19)	N2—C18—C19—C20	−24.7 (3)
C18—N2—C7—O1	−3.2 (3)	N2—C18—C19—C24	158.15 (18)
C1—N2—C7—N1	2.9 (2)	C24—C19—C20—C21	−0.8 (3)
C18—N2—C7—N1	176.23 (16)	C18—C19—C20—C21	−178.0 (2)
C6—N1—C7—O1	176.65 (18)	C19—C20—C21—C22	−0.2 (4)
C8—N1—C7—O1	5.4 (3)	C20—C21—C22—C23	0.7 (4)
C6—N1—C7—N2	−2.83 (19)	C21—C22—C23—C24	−0.1 (4)
C8—N1—C7—N2	−174.11 (16)	C22—C23—C24—C19	−1.0 (3)
C7—N1—C8—C9	−111.65 (19)	C20—C19—C24—C23	1.4 (3)
C6—N1—C8—C9	78.5 (2)	C18—C19—C24—C23	178.7 (2)
N4—N5—C9—C10	0.2 (2)

Symmetry codes: (i) x−1, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+2; (v) x, −y+1/2, z+1/2; (vi) −x+1, −y+1, −z+1; (vii) −x+2, −y+1, −z+1; (viii) −x+1, y+1/2, −z+3/2; (ix) x−1, y, z.

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the triazole ring C (C9/C10/N3–N5).

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N3	0.87	2.04	2.892 (2)	166
O2—H2B···O1^i	0.87	2.00	2.865 (2)	176
C10—H10···O2^v	0.95	2.48	3.402 (3)	164
C13—H13···Cg	0.95	2.83	3.451 (3)	124

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