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

In the title compound, C₂₁H₁₅ClN₄O₃, mol­ecules are linked into chains along the b axis by C—H...O hydrogen bonds. The chains are further connected by inter­molecular C—H...O hydrogen bonds, forming two-dimensional layers parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.089
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O3      ..       3.17 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C21 H15 Cl N4 O3

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.05
           From the CIF: _reflns_number_total               3763
           Count of symmetry unique reflns         1957
           Completeness (_total/calc)            192.28%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1806
           Fraction of Friedel pairs measured     0.923
           Are heavy atom types Z>Si present        yes

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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

---

Computing details

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

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

Crystal data

C21H15ClN4O3	F(000) = 840
Mr = 406.82	Dx = 1.414 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1989 reflections
a = 18.820 (2) Å	θ = 3.0–20.9°
b = 5.3367 (6) Å	µ = 0.23 mm^−1
c = 19.027 (2) Å	T = 293 K
V = 1911.0 (4) Å^3	Column, colourless
Z = 4	0.40 × 0.19 × 0.10 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3763 independent reflections
Radiation source: fine-focus sealed tube	2880 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 2.1°
ω scans	h = −17→23
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→6
Tmin = 0.913, Tmax = 0.977	l = −23→23
10277 measured 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)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.036P)^2 + 0.0701P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
3763 reflections	Δρmax = 0.19 e Å^−3
262 parameters	Δρmin = −0.12 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1811 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (7)

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	0.51070 (4)	0.93581 (18)	0.95559 (5)	0.0874 (3)
O1	0.31226 (10)	1.4545 (3)	0.70681 (11)	0.0594 (5)
O2	0.25989 (9)	1.1709 (3)	0.60809 (9)	0.0492 (4)
O3	0.37208 (10)	1.1997 (4)	0.56904 (10)	0.0668 (6)
N1	0.17014 (11)	1.1145 (4)	0.72733 (11)	0.0493 (5)
N2	0.18000 (12)	1.2249 (5)	0.79117 (12)	0.0639 (7)
N3	0.13520 (15)	1.4095 (5)	0.79787 (13)	0.0724 (7)
N4	0.19053 (14)	1.7362 (5)	0.48168 (16)	0.0882 (9)
C1	0.37176 (15)	1.2972 (5)	0.83571 (14)	0.0516 (7)
H1A	0.3449	1.4433	0.8382	0.062*
C2	0.41532 (16)	1.2347 (6)	0.89093 (14)	0.0592 (7)
H2B	0.4179	1.3366	0.9305	0.071*
C3	0.45516 (14)	1.0186 (5)	0.88679 (14)	0.0544 (7)
C4	0.45198 (14)	0.8681 (5)	0.82843 (14)	0.0534 (7)
H4B	0.4799	0.7247	0.8258	0.064*
C5	0.40721 (13)	0.9298 (5)	0.77361 (14)	0.0487 (6)
H5A	0.4041	0.8248	0.7347	0.058*
C6	0.36682 (13)	1.1471 (4)	0.77608 (13)	0.0404 (6)
C7	0.32237 (12)	1.2328 (5)	0.71655 (13)	0.0418 (6)
C8	0.28554 (14)	1.0428 (4)	0.66950 (14)	0.0443 (6)
H8A	0.3190	0.9108	0.6559	0.053*
C9	0.22054 (14)	0.9275 (4)	0.70473 (15)	0.0507 (7)
H9A	0.1975	0.8143	0.6720	0.061*
H9B	0.2357	0.8302	0.7451	0.061*
C10	0.11743 (13)	1.2353 (5)	0.69191 (13)	0.0471 (6)
C11	0.08611 (16)	1.1973 (6)	0.62688 (15)	0.0640 (8)
H11A	0.1002	1.0690	0.5969	0.077*
C12	0.03236 (17)	1.3633 (8)	0.60948 (19)	0.0795 (10)
H12A	0.0093	1.3451	0.5665	0.095*
C13	0.01171 (18)	1.5566 (7)	0.6543 (2)	0.0829 (11)
H13A	−0.0239	1.6659	0.6400	0.099*
C14	0.04209 (16)	1.5893 (6)	0.7179 (2)	0.0749 (9)
H14A	0.0276	1.7175	0.7477	0.090*
C15	0.09607 (15)	1.4234 (5)	0.73711 (15)	0.0558 (7)
C16	0.31146 (14)	1.2647 (5)	0.56581 (13)	0.0471 (6)
C17	0.28422 (14)	1.4591 (5)	0.51739 (13)	0.0470 (6)
C18	0.32881 (16)	1.5671 (6)	0.46915 (16)	0.0758 (9)
H18A	0.3754	1.5115	0.4647	0.091*
C19	0.3041 (2)	1.7579 (7)	0.42753 (18)	0.0818 (10)
H19A	0.3333	1.8325	0.3941	0.098*
C20	0.23668 (19)	1.8347 (6)	0.43612 (17)	0.0760 (10)
H20A	0.2210	1.9666	0.4082	0.091*
C21	0.21599 (17)	1.5499 (6)	0.52124 (17)	0.0694 (9)
H21A	0.1854	1.4766	0.5537	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0825 (6)	0.1024 (7)	0.0773 (5)	0.0155 (5)	−0.0322 (5)	0.0053 (5)
O1	0.0779 (13)	0.0344 (11)	0.0660 (11)	0.0038 (9)	−0.0131 (10)	0.0064 (9)
O2	0.0458 (11)	0.0522 (10)	0.0497 (10)	0.0018 (9)	−0.0021 (8)	0.0093 (8)
O3	0.0509 (12)	0.0860 (15)	0.0636 (12)	0.0164 (10)	0.0078 (10)	0.0157 (11)
N1	0.0494 (13)	0.0499 (13)	0.0487 (13)	0.0010 (10)	0.0032 (11)	0.0076 (11)
N2	0.0671 (17)	0.0770 (18)	0.0477 (14)	0.0072 (15)	0.0034 (12)	0.0030 (13)
N3	0.0721 (18)	0.0817 (19)	0.0633 (17)	0.0110 (15)	0.0103 (15)	−0.0080 (14)
N4	0.0724 (18)	0.094 (2)	0.099 (2)	0.0158 (15)	−0.0082 (17)	0.0373 (19)
C1	0.0562 (17)	0.0413 (15)	0.0572 (17)	0.0050 (13)	0.0022 (14)	−0.0017 (13)
C2	0.0699 (19)	0.0602 (19)	0.0474 (16)	0.0015 (16)	−0.0042 (15)	−0.0037 (14)
C3	0.0460 (15)	0.0609 (19)	0.0563 (17)	0.0019 (14)	−0.0076 (13)	0.0089 (15)
C4	0.0470 (17)	0.0466 (17)	0.0666 (19)	0.0068 (12)	−0.0055 (14)	0.0029 (14)
C5	0.0534 (15)	0.0392 (14)	0.0535 (15)	0.0034 (12)	0.0008 (13)	−0.0005 (12)
C6	0.0422 (13)	0.0340 (14)	0.0451 (14)	0.0000 (11)	0.0014 (11)	0.0058 (11)
C7	0.0474 (14)	0.0305 (14)	0.0474 (14)	0.0052 (11)	0.0084 (12)	0.0046 (11)
C8	0.0512 (15)	0.0355 (13)	0.0461 (13)	0.0073 (12)	−0.0004 (12)	0.0029 (12)
C9	0.0538 (16)	0.0353 (15)	0.0632 (16)	0.0001 (12)	0.0011 (14)	0.0083 (13)
C10	0.0421 (15)	0.0490 (16)	0.0500 (16)	−0.0047 (12)	0.0065 (13)	0.0093 (13)
C11	0.0541 (18)	0.075 (2)	0.063 (2)	−0.0042 (16)	0.0015 (16)	−0.0001 (17)
C12	0.055 (2)	0.116 (3)	0.068 (2)	0.010 (2)	−0.0093 (17)	0.015 (2)
C13	0.056 (2)	0.092 (3)	0.101 (3)	0.0208 (18)	0.009 (2)	0.029 (2)
C14	0.063 (2)	0.064 (2)	0.097 (3)	0.0131 (16)	0.022 (2)	0.0128 (19)
C15	0.0519 (17)	0.0522 (18)	0.0632 (19)	0.0047 (14)	0.0161 (15)	0.0052 (15)
C16	0.0450 (15)	0.0518 (16)	0.0445 (15)	0.0026 (13)	0.0017 (13)	−0.0016 (13)
C17	0.0527 (16)	0.0502 (16)	0.0381 (13)	0.0011 (13)	−0.0022 (12)	0.0003 (12)
C18	0.072 (2)	0.088 (2)	0.068 (2)	0.0220 (18)	0.0167 (18)	0.0224 (19)
C19	0.095 (3)	0.088 (3)	0.0622 (19)	0.006 (2)	0.0110 (19)	0.0291 (19)
C20	0.104 (3)	0.064 (2)	0.060 (2)	0.005 (2)	−0.018 (2)	0.0165 (16)
C21	0.0583 (18)	0.081 (2)	0.069 (2)	−0.0015 (17)	−0.0011 (16)	0.0216 (18)

Geometric parameters (Å, º)

Cl1—C3	1.732 (3)	C8—C9	1.525 (4)
O1—C7	1.212 (3)	C8—H8A	0.9800
O2—C16	1.356 (3)	C9—H9A	0.9700
O2—C8	1.437 (3)	C9—H9B	0.9700
O3—C16	1.194 (3)	C10—C15	1.382 (4)
N1—C10	1.361 (3)	C10—C11	1.386 (4)
N1—N2	1.363 (3)	C11—C12	1.384 (5)
N1—C9	1.443 (3)	C11—H11A	0.9300
N2—N3	1.303 (3)	C12—C13	1.393 (5)
N3—C15	1.373 (4)	C12—H12A	0.9300
N4—C20	1.335 (4)	C13—C14	1.350 (5)
N4—C21	1.336 (4)	C13—H13A	0.9300
C1—C2	1.374 (4)	C14—C15	1.396 (4)
C1—C6	1.392 (4)	C14—H14A	0.9300
C1—H1A	0.9300	C16—C17	1.479 (4)
C2—C3	1.378 (4)	C17—C18	1.371 (4)
C2—H2B	0.9300	C17—C21	1.375 (4)
C3—C4	1.372 (4)	C18—C19	1.372 (4)
C4—C5	1.381 (4)	C18—H18A	0.9300
C4—H4B	0.9300	C19—C20	1.343 (5)
C5—C6	1.388 (3)	C19—H19A	0.9300
C5—H5A	0.9300	C20—H20A	0.9300
C6—C7	1.480 (3)	C21—H21A	0.9300
C7—C8	1.520 (4)
C16—O2—C8	114.7 (2)	C8—C9—H9B	109.1
C10—N1—N2	109.6 (2)	H9A—C9—H9B	107.9
C10—N1—C9	131.2 (2)	N1—C10—C15	104.4 (2)
N2—N1—C9	118.4 (2)	N1—C10—C11	133.1 (3)
N3—N2—N1	109.0 (2)	C15—C10—C11	122.6 (3)
N2—N3—C15	107.8 (2)	C12—C11—C10	115.5 (3)
C20—N4—C21	115.2 (3)	C12—C11—H11A	122.2
C2—C1—C6	121.6 (2)	C10—C11—H11A	122.2
C2—C1—H1A	119.2	C11—C12—C13	122.1 (3)
C6—C1—H1A	119.2	C11—C12—H12A	119.0
C1—C2—C3	119.0 (3)	C13—C12—H12A	119.0
C1—C2—H2B	120.5	C14—C13—C12	121.7 (3)
C3—C2—H2B	120.5	C14—C13—H13A	119.1
C4—C3—C2	120.8 (2)	C12—C13—H13A	119.1
C4—C3—Cl1	119.3 (2)	C13—C14—C15	117.5 (3)
C2—C3—Cl1	119.9 (2)	C13—C14—H14A	121.3
C3—C4—C5	119.9 (2)	C15—C14—H14A	121.3
C3—C4—H4B	120.0	N3—C15—C10	109.2 (2)
C5—C4—H4B	120.0	N3—C15—C14	130.2 (3)
C4—C5—C6	120.5 (2)	C10—C15—C14	120.6 (3)
C4—C5—H5A	119.7	O3—C16—O2	123.1 (2)
C6—C5—H5A	119.7	O3—C16—C17	124.5 (2)
C5—C6—C1	118.2 (2)	O2—C16—C17	112.4 (2)
C5—C6—C7	122.8 (2)	C18—C17—C21	117.3 (3)
C1—C6—C7	118.9 (2)	C18—C17—C16	120.0 (2)
O1—C7—C6	120.5 (2)	C21—C17—C16	122.5 (2)
O1—C7—C8	119.3 (2)	C17—C18—C19	119.4 (3)
C6—C7—C8	120.2 (2)	C17—C18—H18A	120.3
O2—C8—C7	108.34 (18)	C19—C18—H18A	120.3
O2—C8—C9	106.3 (2)	C20—C19—C18	118.5 (3)
C7—C8—C9	112.1 (2)	C20—C19—H19A	120.8
O2—C8—H8A	110.0	C18—C19—H19A	120.8
C7—C8—H8A	110.0	N4—C20—C19	125.0 (3)
C9—C8—H8A	110.0	N4—C20—H20A	117.5
N1—C9—C8	112.3 (2)	C19—C20—H20A	117.5
N1—C9—H9A	109.1	N4—C21—C17	124.6 (3)
C8—C9—H9A	109.1	N4—C21—H21A	117.7
N1—C9—H9B	109.1	C17—C21—H21A	117.7
C10—N1—N2—N3	0.6 (3)	N2—N1—C10—C11	−178.6 (3)
C9—N1—N2—N3	171.6 (2)	C9—N1—C10—C11	11.8 (5)
N1—N2—N3—C15	−1.0 (3)	N1—C10—C11—C12	179.4 (3)
C6—C1—C2—C3	0.3 (4)	C15—C10—C11—C12	0.9 (4)
C1—C2—C3—C4	0.4 (4)	C10—C11—C12—C13	0.5 (5)
C1—C2—C3—Cl1	179.8 (2)	C11—C12—C13—C14	−1.4 (5)
C2—C3—C4—C5	−1.5 (4)	C12—C13—C14—C15	0.8 (5)
Cl1—C3—C4—C5	179.1 (2)	N2—N3—C15—C10	1.1 (3)
C3—C4—C5—C6	1.9 (4)	N2—N3—C15—C14	−179.3 (3)
C4—C5—C6—C1	−1.3 (4)	N1—C10—C15—N3	−0.7 (3)
C4—C5—C6—C7	175.0 (2)	C11—C10—C15—N3	178.2 (2)
C2—C1—C6—C5	0.2 (4)	N1—C10—C15—C14	179.6 (3)
C2—C1—C6—C7	−176.2 (2)	C11—C10—C15—C14	−1.5 (4)
C5—C6—C7—O1	−149.1 (2)	C13—C14—C15—N3	−179.0 (3)
C1—C6—C7—O1	27.1 (4)	C13—C14—C15—C10	0.6 (4)
C5—C6—C7—C8	34.4 (3)	C8—O2—C16—O3	16.8 (3)
C1—C6—C7—C8	−149.4 (2)	C8—O2—C16—C17	−161.64 (19)
C16—O2—C8—C7	65.7 (3)	O3—C16—C17—C18	4.0 (4)
C16—O2—C8—C9	−173.7 (2)	O2—C16—C17—C18	−177.6 (2)
O1—C7—C8—O2	16.2 (3)	O3—C16—C17—C21	−171.8 (3)
C6—C7—C8—O2	−167.3 (2)	O2—C16—C17—C21	6.6 (4)
O1—C7—C8—C9	−100.8 (3)	C21—C17—C18—C19	0.1 (5)
C6—C7—C8—C9	75.8 (3)	C16—C17—C18—C19	−176.0 (3)
C10—N1—C9—C8	83.9 (3)	C17—C18—C19—C20	0.7 (5)
N2—N1—C9—C8	−84.9 (3)	C21—N4—C20—C19	0.9 (5)
O2—C8—C9—N1	−62.2 (3)	C18—C19—C20—N4	−1.3 (6)
C7—C8—C9—N1	55.9 (3)	C20—N4—C21—C17	0.0 (5)
N2—N1—C10—C15	0.1 (3)	C18—C17—C21—N4	−0.4 (5)
C9—N1—C10—C15	−169.4 (2)	C16—C17—C21—N4	175.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O1^i	0.97	2.57	3.058 (3)	111
C13—H13A···O3^ii	0.93	2.49	3.351 (4)	155
C21—H21A···O2	0.93	2.39	2.739 (4)	102

Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y+3, z.