2-(1H-1,2,3-Benzotriazol-1-ylmeth­yl)-1-(2,4-dichloro­benzo­yl)ethyl nicotinate monohydrate

The mol­ecules of the title compound, C₂₁H₁₄Cl₂N₄O₃·H₂O, are linked into dimers by C—H...O hydrogen bonds and are linked into chains along the b axis by C—H...O and O—H...N hydrogen bonds involving the solvent water mol­ecule. The packing is further stabilized by π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.108
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

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
   0 ALERT level B = Potentially serious problem
   3 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
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-(1H-1,2,3-Benzotriazol-1-ylmethyl)-1-(2,4-dichlorobenzoyl)ethyl nicotinate monohydrate

Crystal data

C21H14Cl2N4O3·H2O	F(000) = 944
Mr = 459.28	Dx = 1.469 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3489 reflections
a = 11.211 (3) Å	θ = 2.4–25.1°
b = 13.035 (3) Å	µ = 0.35 mm^−1
c = 14.231 (3) Å	T = 293 K
β = 92.910 (3)°	Block, yellow
V = 2077.1 (8) Å^3	0.45 × 0.24 × 0.13 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	4118 independent reflections
Radiation source: fine-focus sealed tube	3110 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 1.8°
ω scans	h = −13→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −15→16
Tmin = 0.859, Tmax = 0.956	l = −17→17
11426 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0573P)^2 + 0.497P] where P = (Fo^2 + 2Fc^2)/3
4118 reflections	(Δ/σ)max < 0.001
288 parameters	Δρmax = 0.21 e Å^−3
2 restraints	Δρmin = −0.18 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
Cl1	0.82183 (5)	0.75717 (4)	0.17513 (4)	0.06782 (19)
Cl2	1.05495 (7)	0.63418 (5)	0.48988 (5)	0.0894 (2)
O1	0.87270 (13)	1.18055 (12)	0.32936 (11)	0.0706 (4)
O2	0.69208 (11)	1.13075 (9)	0.27236 (9)	0.0490 (3)
O3	0.82570 (15)	0.98937 (12)	0.19369 (10)	0.0716 (4)
O1W	0.44877 (17)	1.15223 (13)	0.46861 (12)	0.0714 (5)
H1W1	0.5146 (14)	1.145 (2)	0.4995 (16)	0.087 (9)*
H2W1	0.462 (3)	1.2052 (14)	0.4360 (17)	0.104 (10)*
N1	0.53569 (14)	0.95093 (11)	0.24340 (11)	0.0483 (4)
N2	0.54917 (17)	0.85259 (12)	0.21547 (14)	0.0622 (5)
N3	0.48738 (17)	0.83960 (13)	0.13625 (14)	0.0655 (5)
N4	0.65894 (16)	1.37829 (13)	0.09611 (12)	0.0594 (5)
C1	0.67806 (17)	1.29523 (15)	0.14968 (13)	0.0507 (5)
H1A	0.6311	1.2375	0.1372	0.061*
C2	0.7277 (2)	1.46032 (16)	0.11610 (15)	0.0596 (5)
H2B	0.7143	1.5196	0.0807	0.072*
C3	0.8163 (2)	1.46171 (16)	0.18562 (16)	0.0621 (6)
H3B	0.8630	1.5200	0.1959	0.075*
C4	0.83535 (19)	1.37551 (15)	0.24023 (15)	0.0559 (5)
H4B	0.8951	1.3745	0.2880	0.067*
C5	0.76398 (16)	1.29053 (14)	0.22279 (13)	0.0447 (4)
C6	0.78405 (17)	1.19699 (14)	0.28039 (13)	0.0481 (4)
C7	0.71153 (17)	1.03654 (13)	0.32325 (13)	0.0460 (4)
H7A	0.7448	1.0528	0.3865	0.055*
C8	0.59182 (18)	0.98464 (15)	0.33208 (13)	0.0523 (5)
H8A	0.6026	0.9257	0.3732	0.063*
H8B	0.5385	1.0320	0.3616	0.063*
C9	0.43159 (17)	0.92995 (16)	0.11180 (14)	0.0543 (5)
C10	0.3549 (2)	0.9563 (2)	0.03470 (16)	0.0706 (6)
H10A	0.3333	0.9086	−0.0116	0.085*
C11	0.3134 (2)	1.0542 (2)	0.03014 (17)	0.0738 (7)
H11A	0.2621	1.0736	−0.0202	0.089*
C12	0.34598 (19)	1.12661 (17)	0.09950 (17)	0.0646 (6)
H12A	0.3163	1.1930	0.0934	0.077*
C13	0.41995 (17)	1.10308 (15)	0.17598 (14)	0.0525 (5)
H13A	0.4407	1.1513	0.2221	0.063*
C14	0.46230 (15)	1.00253 (14)	0.18055 (13)	0.0449 (4)
C15	0.80150 (17)	0.97076 (14)	0.27346 (12)	0.0469 (4)
C16	0.85664 (16)	0.88333 (13)	0.32773 (12)	0.0426 (4)
C17	0.87577 (17)	0.78675 (14)	0.28813 (12)	0.0466 (4)
C18	0.93554 (18)	0.71077 (15)	0.33840 (14)	0.0531 (5)
H18A	0.9468	0.6467	0.3115	0.064*
C19	0.97852 (18)	0.73046 (15)	0.42891 (14)	0.0538 (5)
C20	0.96192 (18)	0.82406 (16)	0.47081 (14)	0.0552 (5)
H20A	0.9915	0.8365	0.5320	0.066*
C21	0.90042 (17)	0.89910 (14)	0.42005 (13)	0.0486 (4)
H21A	0.8878	0.9622	0.4483	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0852 (4)	0.0662 (4)	0.0507 (3)	0.0175 (3)	−0.0103 (3)	−0.0142 (2)
Cl2	0.1157 (6)	0.0732 (4)	0.0774 (4)	0.0445 (4)	−0.0125 (4)	0.0130 (3)
O1	0.0637 (9)	0.0697 (10)	0.0754 (10)	−0.0088 (8)	−0.0280 (8)	0.0170 (8)
O2	0.0516 (8)	0.0381 (7)	0.0560 (8)	0.0011 (6)	−0.0093 (6)	0.0070 (5)
O3	0.1042 (12)	0.0649 (9)	0.0469 (8)	0.0173 (9)	0.0176 (8)	0.0137 (7)
O1W	0.0870 (13)	0.0556 (10)	0.0699 (10)	−0.0151 (9)	−0.0134 (9)	0.0080 (8)
N1	0.0520 (9)	0.0355 (8)	0.0578 (9)	−0.0006 (7)	0.0072 (8)	0.0003 (7)
N2	0.0687 (11)	0.0354 (9)	0.0841 (13)	0.0002 (8)	0.0179 (10)	0.0000 (8)
N3	0.0695 (12)	0.0450 (10)	0.0831 (13)	−0.0082 (9)	0.0146 (10)	−0.0170 (9)
N4	0.0631 (11)	0.0515 (10)	0.0627 (10)	0.0079 (8)	−0.0062 (9)	0.0104 (8)
C1	0.0528 (11)	0.0428 (10)	0.0558 (11)	0.0013 (9)	−0.0046 (9)	0.0001 (9)
C2	0.0678 (14)	0.0441 (11)	0.0678 (13)	0.0107 (10)	0.0105 (11)	0.0117 (10)
C3	0.0686 (14)	0.0399 (11)	0.0781 (15)	−0.0053 (10)	0.0052 (12)	−0.0017 (10)
C4	0.0568 (12)	0.0506 (12)	0.0596 (12)	−0.0021 (9)	−0.0051 (10)	−0.0034 (9)
C5	0.0449 (10)	0.0406 (10)	0.0484 (10)	0.0036 (8)	0.0008 (8)	−0.0008 (8)
C6	0.0491 (11)	0.0459 (11)	0.0486 (10)	−0.0002 (9)	−0.0054 (9)	−0.0004 (8)
C7	0.0550 (11)	0.0404 (10)	0.0419 (9)	0.0043 (8)	−0.0043 (8)	0.0059 (8)
C8	0.0595 (12)	0.0488 (11)	0.0492 (10)	0.0049 (9)	0.0078 (9)	0.0076 (9)
C9	0.0488 (11)	0.0512 (12)	0.0639 (12)	−0.0100 (9)	0.0138 (10)	−0.0113 (10)
C10	0.0593 (14)	0.0879 (18)	0.0646 (14)	−0.0157 (13)	0.0032 (11)	−0.0201 (13)
C11	0.0559 (13)	0.099 (2)	0.0659 (14)	−0.0003 (14)	−0.0051 (11)	0.0034 (13)
C12	0.0529 (12)	0.0635 (14)	0.0773 (15)	0.0072 (11)	0.0033 (11)	0.0099 (11)
C13	0.0484 (11)	0.0459 (11)	0.0633 (12)	0.0007 (9)	0.0025 (9)	−0.0010 (9)
C14	0.0409 (10)	0.0416 (10)	0.0526 (10)	−0.0047 (8)	0.0080 (8)	−0.0009 (8)
C15	0.0549 (11)	0.0446 (10)	0.0407 (9)	−0.0013 (8)	−0.0008 (8)	0.0037 (8)
C16	0.0443 (10)	0.0423 (10)	0.0412 (9)	0.0034 (8)	0.0024 (8)	0.0032 (7)
C17	0.0485 (10)	0.0485 (11)	0.0427 (9)	0.0029 (8)	0.0016 (8)	−0.0021 (8)
C18	0.0585 (12)	0.0433 (11)	0.0574 (12)	0.0086 (9)	0.0035 (10)	−0.0014 (9)
C19	0.0553 (12)	0.0510 (11)	0.0548 (11)	0.0117 (9)	0.0009 (9)	0.0102 (9)
C20	0.0602 (12)	0.0610 (12)	0.0437 (10)	0.0099 (10)	−0.0046 (9)	0.0036 (9)
C21	0.0537 (11)	0.0463 (10)	0.0456 (10)	0.0068 (9)	−0.0003 (9)	−0.0016 (8)

Geometric parameters (Å, º)

Cl1—C17	1.7325 (18)	C7—C15	1.525 (3)
Cl2—C19	1.7283 (19)	C7—H7A	0.9800
O1—C6	1.204 (2)	C8—H8A	0.9700
O2—C6	1.345 (2)	C8—H8B	0.9700
O2—C7	1.437 (2)	C9—C14	1.392 (3)
O3—C15	1.205 (2)	C9—C10	1.402 (3)
O1W—H1W1	0.844 (10)	C10—C11	1.359 (3)
O1W—H2W1	0.849 (10)	C10—H10A	0.9300
N1—N2	1.353 (2)	C11—C12	1.400 (3)
N1—C14	1.362 (2)	C11—H11A	0.9300
N1—C8	1.449 (2)	C12—C13	1.369 (3)
N2—N3	1.304 (3)	C12—H12A	0.9300
N3—C9	1.370 (3)	C13—C14	1.394 (3)
N4—C1	1.335 (2)	C13—H13A	0.9300
N4—C2	1.340 (3)	C15—C16	1.493 (2)
C1—C5	1.383 (3)	C16—C21	1.394 (2)
C1—H1A	0.9300	C16—C17	1.400 (2)
C2—C3	1.366 (3)	C17—C18	1.376 (3)
C2—H2B	0.9300	C18—C19	1.376 (3)
C3—C4	1.377 (3)	C18—H18A	0.9300
C3—H3B	0.9300	C19—C20	1.375 (3)
C4—C5	1.382 (3)	C20—C21	1.380 (3)
C4—H4B	0.9300	C20—H20A	0.9300
C5—C6	1.480 (3)	C21—H21A	0.9300
C7—C8	1.514 (3)
C6—O2—C7	114.19 (14)	N3—C9—C10	131.6 (2)
H1W1—O1W—H2W1	102 (3)	C14—C9—C10	120.2 (2)
N2—N1—C14	110.35 (16)	C11—C10—C9	117.6 (2)
N2—N1—C8	119.55 (16)	C11—C10—H10A	121.2
C14—N1—C8	130.03 (15)	C9—C10—H10A	121.2
N3—N2—N1	108.35 (17)	C10—C11—C12	121.5 (2)
N2—N3—C9	108.88 (16)	C10—C11—H11A	119.3
C1—N4—C2	116.86 (18)	C12—C11—H11A	119.3
N4—C1—C5	123.44 (18)	C13—C12—C11	122.4 (2)
N4—C1—H1A	118.3	C13—C12—H12A	118.8
C5—C1—H1A	118.3	C11—C12—H12A	118.8
N4—C2—C3	123.61 (19)	C12—C13—C14	116.02 (19)
N4—C2—H2B	118.2	C12—C13—H13A	122.0
C3—C2—H2B	118.2	C14—C13—H13A	122.0
C2—C3—C4	119.0 (2)	N1—C14—C9	104.22 (17)
C2—C3—H3B	120.5	N1—C14—C13	133.45 (17)
C4—C3—H3B	120.5	C9—C14—C13	122.33 (19)
C3—C4—C5	118.76 (19)	O3—C15—C16	122.26 (18)
C3—C4—H4B	120.6	O3—C15—C7	120.67 (17)
C5—C4—H4B	120.6	C16—C15—C7	117.07 (15)
C4—C5—C1	118.33 (17)	C21—C16—C17	117.26 (16)
C4—C5—C6	119.38 (17)	C21—C16—C15	119.45 (16)
C1—C5—C6	122.26 (17)	C17—C16—C15	123.09 (16)
O1—C6—O2	122.80 (17)	C18—C17—C16	121.23 (17)
O1—C6—C5	124.41 (18)	C18—C17—Cl1	117.41 (15)
O2—C6—C5	112.79 (15)	C16—C17—Cl1	121.35 (14)
O2—C7—C8	108.14 (14)	C17—C18—C19	119.38 (18)
O2—C7—C15	109.47 (15)	C17—C18—H18A	120.3
C8—C7—C15	113.41 (15)	C19—C18—H18A	120.3
O2—C7—H7A	108.6	C20—C19—C18	121.52 (17)
C8—C7—H7A	108.6	C20—C19—Cl2	120.09 (15)
C15—C7—H7A	108.6	C18—C19—Cl2	118.40 (15)
N1—C8—C7	114.25 (15)	C19—C20—C21	118.50 (18)
N1—C8—H8A	108.7	C19—C20—H20A	120.8
C7—C8—H8A	108.7	C21—C20—H20A	120.8
N1—C8—H8B	108.7	C20—C21—C16	122.11 (18)
C7—C8—H8B	108.7	C20—C21—H21A	118.9
H8A—C8—H8B	107.6	C16—C21—H21A	118.9
N3—C9—C14	108.20 (18)
C14—N1—N2—N3	0.4 (2)	C8—N1—C14—C9	−176.92 (17)
C8—N1—N2—N3	177.56 (16)	N2—N1—C14—C13	179.9 (2)
N1—N2—N3—C9	−0.5 (2)	C8—N1—C14—C13	3.2 (3)
C2—N4—C1—C5	−0.2 (3)	N3—C9—C14—N1	−0.1 (2)
C1—N4—C2—C3	1.7 (3)	C10—C9—C14—N1	179.64 (17)
N4—C2—C3—C4	−1.6 (3)	N3—C9—C14—C13	179.83 (17)
C2—C3—C4—C5	0.0 (3)	C10—C9—C14—C13	−0.4 (3)
C3—C4—C5—C1	1.4 (3)	C12—C13—C14—N1	179.87 (19)
C3—C4—C5—C6	179.49 (19)	C12—C13—C14—C9	0.0 (3)
N4—C1—C5—C4	−1.3 (3)	O2—C7—C15—O3	−15.5 (2)
N4—C1—C5—C6	−179.34 (19)	C8—C7—C15—O3	105.3 (2)
C7—O2—C6—O1	−3.1 (3)	O2—C7—C15—C16	164.71 (15)
C7—O2—C6—C5	176.67 (15)	C8—C7—C15—C16	−74.4 (2)
C4—C5—C6—O1	−15.7 (3)	O3—C15—C16—C21	133.9 (2)
C1—C5—C6—O1	162.4 (2)	C7—C15—C16—C21	−46.4 (2)
C4—C5—C6—O2	164.53 (17)	O3—C15—C16—C17	−40.8 (3)
C1—C5—C6—O2	−17.4 (3)	C7—C15—C16—C17	138.90 (18)
C6—O2—C7—C8	163.48 (15)	C21—C16—C17—C18	−0.1 (3)
C6—O2—C7—C15	−72.52 (19)	C15—C16—C17—C18	174.69 (18)
N2—N1—C8—C7	96.1 (2)	C21—C16—C17—Cl1	178.20 (14)
C14—N1—C8—C7	−87.5 (2)	C15—C16—C17—Cl1	−7.0 (3)
O2—C7—C8—N1	65.8 (2)	C16—C17—C18—C19	−0.8 (3)
C15—C7—C8—N1	−55.8 (2)	Cl1—C17—C18—C19	−179.14 (16)
N2—N3—C9—C14	0.4 (2)	C17—C18—C19—C20	0.8 (3)
N2—N3—C9—C10	−179.3 (2)	C17—C18—C19—Cl2	−179.17 (15)
N3—C9—C10—C11	180.0 (2)	C18—C19—C20—C21	0.1 (3)
C14—C9—C10—C11	0.3 (3)	Cl2—C19—C20—C21	−179.96 (16)
C9—C10—C11—C12	0.2 (3)	C19—C20—C21—C16	−1.0 (3)
C10—C11—C12—C13	−0.7 (4)	C17—C16—C21—C20	1.0 (3)
C11—C12—C13—C14	0.6 (3)	C15—C16—C21—C20	−173.99 (18)
N2—N1—C14—C9	−0.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···N3^i	0.85 (2)	2.12 (2)	2.969 (3)	174 (3)
C1—H1A···O2	0.93	2.44	2.764 (2)	100
C2—H2B···O1W^i	0.93	2.59	3.374 (3)	143
C8—H8A···O1W^ii	0.97	2.56	3.401 (3)	145
C8—H8B···O1W	0.97	2.44	3.382 (3)	164
C20—H20A···O1^iii	0.93	2.44	3.316 (3)	157

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