2-(1H-Benzotriazol-1-yl)-1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone cyclo­hexane hemisolvate

In the title compound, C₁₆H₁₂N₆O·0.5C₆H₁₂, the disordered mol­ecule of cyclo­hexane lies on a centre of symmetry. In the crystal structure, mol­ecules are linked into double chains along the b axis by inter­molecular C—H...N inter­actions. The packing is further stabilized by C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.050
• wR factor = 0.149
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      43.40 Deg.
              C17B -C18  -C17A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.20 Deg.
              C17B -C19  -C17A    1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C16 H12 N6 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C6 H12

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   4 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-Benzotriazol-1-yl)-1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone cyclohexane hemisolvate

Crystal data

C16H12N6O·0.5C6H12	F(000) = 728
Mr = 346.39	Dx = 1.292 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.9187 (12) Å	Cell parameters from 3808 reflections
b = 8.3101 (11) Å	θ = 2.4–25.5°
c = 25.367 (3) Å	µ = 0.09 mm^−1
β = 108.718 (4)°	T = 293 K
V = 1780.6 (4) Å^3	Block, colourless
Z = 4	0.30 × 0.20 × 0.09 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	3479 independent reflections
Radiation source: fine-focus sealed tube	2832 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −11→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→10
Tmin = 0.975, Tmax = 0.992	l = −31→31
9620 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0928P)^2 + 0.5045P] where P = (Fo^2 + 2Fc^2)/3
3479 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.34 e Å^−3
2 restraints	Δρmin = −0.29 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	Occ. (<1)
O1	−0.00484 (17)	−0.39807 (16)	−0.32650 (6)	0.0681 (4)
N1	0.26308 (15)	−0.20208 (15)	−0.36971 (5)	0.0406 (3)
N2	0.38371 (17)	−0.09458 (17)	−0.36185 (6)	0.0512 (4)
N3	0.37767 (19)	−0.03470 (18)	−0.40949 (6)	0.0579 (4)
N4	0.30576 (17)	−0.44732 (15)	−0.31817 (5)	0.0465 (4)
N5	0.4471 (2)	−0.6610 (2)	−0.28881 (7)	0.0681 (5)
N6	0.2653 (2)	−0.54880 (17)	−0.36255 (6)	0.0605 (4)
C1	−0.1595 (2)	−0.0926 (3)	−0.34004 (8)	0.0611 (5)
H1A	−0.2253	−0.1809	−0.3527	0.073*
C2	−0.2244 (2)	0.0578 (3)	−0.33958 (9)	0.0705 (6)
H2B	−0.3338	0.0701	−0.3525	0.085*
C3	−0.1303 (3)	0.1887 (3)	−0.32043 (8)	0.0642 (5)
H3B	−0.1754	0.2897	−0.3204	0.077*
C4	0.0314 (2)	0.1707 (2)	−0.30115 (8)	0.0593 (5)
H4A	0.0958	0.2593	−0.2874	0.071*
C5	0.0984 (2)	0.0218 (2)	−0.30206 (7)	0.0508 (4)
H5B	0.2080	0.0111	−0.2895	0.061*
C6	0.0042 (2)	−0.1128 (2)	−0.32157 (6)	0.0459 (4)
C7	0.0706 (2)	−0.2761 (2)	−0.32350 (6)	0.0466 (4)
C8	0.2449 (2)	−0.28446 (18)	−0.32207 (6)	0.0430 (4)
H8A	0.3086	−0.2265	−0.2888	0.052*
C9	0.17670 (19)	−0.21057 (18)	−0.42509 (6)	0.0406 (4)
C10	0.0448 (2)	−0.3004 (2)	−0.45572 (7)	0.0491 (4)
H10A	−0.0048	−0.3734	−0.4390	0.059*
C11	−0.0064 (2)	−0.2736 (2)	−0.51211 (7)	0.0605 (5)
H11A	−0.0940	−0.3301	−0.5342	0.073*
C12	0.0684 (3)	−0.1643 (3)	−0.53759 (7)	0.0659 (6)
H12A	0.0290	−0.1505	−0.5760	0.079*
C13	0.1972 (3)	−0.0779 (2)	−0.50765 (8)	0.0627 (5)
H13A	0.2469	−0.0058	−0.5247	0.075*
C14	0.2516 (2)	−0.10266 (19)	−0.44993 (7)	0.0481 (4)
C15	0.4124 (2)	−0.5170 (2)	−0.27554 (7)	0.0586 (5)
H15A	0.4568	−0.4698	−0.2408	0.070*
C16	0.3544 (3)	−0.6734 (2)	−0.34247 (8)	0.0618 (5)
H16A	0.3541	−0.7647	−0.3637	0.074*
C17A	0.3670 (14)	−1.0196 (9)	−0.0469 (5)	0.167 (6)	0.44
H17A	0.3180	−1.0166	−0.0870	0.201*	0.44
H17B	0.2880	−1.0557	−0.0307	0.201*	0.44
C17B	0.4661 (13)	−0.9801 (11)	−0.0588 (3)	0.142 (3)	0.56
H17D	0.5605	−0.9421	−0.0660	0.170*	0.56
H17C	0.3837	−0.9920	−0.0945	0.170*	0.56
C18	0.4988 (8)	−1.1349 (5)	−0.0328 (3)	0.164 (2)
H18A	0.4582	−1.2415	−0.0452	0.197*
H18B	0.5724	−1.1054	−0.0522	0.197*
C19	0.4175 (6)	−0.8612 (5)	−0.0272 (2)	0.1494 (16)
H19A	0.3264	−0.7906	−0.0349	0.179*
H19B	0.4872	−0.8192	−0.0465	0.179*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0752 (9)	0.0518 (8)	0.0798 (10)	−0.0175 (7)	0.0282 (8)	−0.0047 (6)
N1	0.0428 (7)	0.0355 (7)	0.0370 (7)	−0.0023 (5)	0.0037 (5)	−0.0017 (5)
N2	0.0518 (8)	0.0442 (8)	0.0529 (8)	−0.0097 (6)	0.0102 (7)	−0.0054 (6)
N3	0.0656 (9)	0.0492 (9)	0.0600 (9)	−0.0112 (7)	0.0216 (8)	−0.0015 (7)
N4	0.0567 (8)	0.0367 (7)	0.0354 (6)	0.0020 (6)	0.0000 (6)	−0.0008 (5)
N5	0.0814 (11)	0.0511 (9)	0.0564 (10)	0.0178 (8)	0.0004 (8)	0.0054 (7)
N6	0.0844 (11)	0.0410 (8)	0.0406 (7)	0.0072 (7)	−0.0015 (7)	−0.0051 (6)
C1	0.0514 (10)	0.0674 (12)	0.0607 (11)	−0.0078 (9)	0.0127 (8)	−0.0017 (9)
C2	0.0511 (10)	0.0852 (15)	0.0729 (13)	0.0119 (11)	0.0168 (10)	0.0040 (11)
C3	0.0698 (13)	0.0644 (12)	0.0614 (12)	0.0162 (10)	0.0252 (10)	0.0025 (9)
C4	0.0691 (12)	0.0526 (11)	0.0589 (11)	−0.0003 (9)	0.0241 (9)	−0.0086 (8)
C5	0.0492 (9)	0.0506 (10)	0.0506 (9)	−0.0009 (8)	0.0132 (8)	−0.0068 (7)
C6	0.0502 (9)	0.0498 (9)	0.0365 (8)	−0.0015 (7)	0.0121 (7)	0.0017 (6)
C7	0.0546 (10)	0.0468 (9)	0.0340 (8)	−0.0070 (8)	0.0080 (7)	−0.0018 (6)
C8	0.0520 (9)	0.0356 (8)	0.0330 (7)	−0.0001 (7)	0.0017 (7)	−0.0019 (6)
C9	0.0460 (8)	0.0347 (8)	0.0366 (8)	0.0072 (6)	0.0068 (6)	0.0004 (6)
C10	0.0495 (9)	0.0475 (9)	0.0412 (9)	−0.0012 (7)	0.0017 (7)	−0.0016 (7)
C11	0.0611 (11)	0.0645 (12)	0.0417 (9)	0.0078 (9)	−0.0036 (8)	−0.0076 (8)
C12	0.0860 (15)	0.0714 (13)	0.0353 (9)	0.0203 (11)	0.0124 (9)	0.0042 (8)
C13	0.0856 (14)	0.0573 (11)	0.0508 (10)	0.0108 (10)	0.0299 (10)	0.0101 (8)
C14	0.0574 (10)	0.0390 (8)	0.0485 (9)	0.0055 (7)	0.0176 (8)	0.0016 (7)
C15	0.0675 (12)	0.0514 (10)	0.0410 (9)	0.0092 (9)	−0.0049 (8)	0.0025 (7)
C16	0.0848 (14)	0.0397 (9)	0.0524 (10)	0.0097 (9)	0.0102 (9)	−0.0016 (8)
C17A	0.141 (9)	0.153 (10)	0.147 (9)	−0.077 (8)	−0.039 (7)	0.063 (7)
C17B	0.170 (8)	0.157 (7)	0.100 (4)	0.056 (6)	0.046 (5)	−0.002 (5)
C18	0.259 (7)	0.096 (3)	0.178 (5)	−0.029 (3)	0.129 (5)	−0.046 (3)
C19	0.149 (4)	0.126 (3)	0.187 (5)	0.046 (3)	0.073 (3)	0.049 (3)

Geometric parameters (Å, º)

O1—C7	1.205 (2)	C9—C14	1.385 (2)
N1—N2	1.3630 (19)	C9—C10	1.399 (2)
N1—C9	1.3702 (19)	C10—C11	1.373 (2)
N1—C8	1.443 (2)	C10—H10A	0.9300
N2—N3	1.292 (2)	C11—C12	1.401 (3)
N3—C14	1.377 (2)	C11—H11A	0.9300
N4—C15	1.322 (2)	C12—C13	1.361 (3)
N4—N6	1.3594 (18)	C12—H12A	0.9300
N4—C8	1.450 (2)	C13—C14	1.402 (2)
N5—C15	1.307 (2)	C13—H13A	0.9300
N5—C16	1.351 (2)	C15—H15A	0.9300
N6—C16	1.305 (2)	C16—H16A	0.9300
C1—C2	1.379 (3)	C17A—C19	1.428 (6)
C1—C6	1.393 (3)	C17A—C18	1.469 (12)
C1—H1A	0.9300	C17A—H17A	0.9700
C2—C3	1.365 (3)	C17A—H17B	0.9700
C2—H2B	0.9300	C17B—C19	1.425 (6)
C3—C4	1.374 (3)	C17B—C18	1.433 (9)
C3—H3B	0.9300	C17B—H17D	0.9700
C4—C5	1.378 (3)	C17B—H17C	0.9700
C4—H4A	0.9300	C18—C19^i	1.465 (7)
C5—C6	1.391 (2)	C18—H18A	0.9700
C5—H5B	0.9300	C18—H18B	0.9700
C6—C7	1.487 (2)	C19—C18^i	1.465 (7)
C7—C8	1.545 (3)	C19—H19A	0.9700
C8—H8A	0.9800	C19—H19B	0.9700
N2—N1—C9	109.96 (13)	C13—C12—H12A	119.1
N2—N1—C8	118.96 (12)	C11—C12—H12A	119.1
C9—N1—C8	131.08 (13)	C12—C13—C14	116.90 (18)
N3—N2—N1	108.76 (13)	C12—C13—H13A	121.6
N2—N3—C14	108.53 (14)	C14—C13—H13A	121.6
C15—N4—N6	109.61 (14)	N3—C14—C9	108.94 (15)
C15—N4—C8	128.30 (14)	N3—C14—C13	130.09 (17)
N6—N4—C8	121.91 (12)	C9—C14—C13	120.97 (17)
C15—N5—C16	102.12 (15)	N5—C15—N4	110.98 (16)
C16—N6—N4	101.68 (14)	N5—C15—H15A	124.5
C2—C1—C6	120.26 (19)	N4—C15—H15A	124.5
C2—C1—H1A	119.9	N6—C16—N5	115.61 (16)
C6—C1—H1A	119.9	N6—C16—H16A	122.2
C3—C2—C1	120.93 (19)	N5—C16—H16A	122.2
C3—C2—H2B	119.5	C19—C17A—C18	112.2 (7)
C1—C2—H2B	119.5	C19—C17A—H17A	109.2
C2—C3—C4	119.64 (19)	C18—C17A—H17A	109.2
C2—C3—H3B	120.2	C19—C17A—H17B	109.2
C4—C3—H3B	120.2	C18—C17A—H17B	109.2
C3—C4—C5	120.24 (19)	H17A—C17A—H17B	107.9
C3—C4—H4A	119.9	C19—C17B—C18	114.6 (6)
C5—C4—H4A	119.9	C19—C17B—H17D	108.6
C4—C5—C6	120.83 (17)	C18—C17B—H17D	108.6
C4—C5—H5B	119.6	C19—C17B—H17C	108.6
C6—C5—H5B	119.6	C18—C17B—H17C	108.6
C5—C6—C1	118.09 (17)	H17D—C17B—H17C	107.6
C5—C6—C7	122.96 (15)	C17B—C18—C19^i	117.3 (5)
C1—C6—C7	118.95 (16)	C17B—C18—C17A	43.4 (5)
O1—C7—C6	123.31 (17)	C19^i—C18—C17A	111.6 (6)
O1—C7—C8	120.04 (16)	C17B—C18—H18A	132.1
C6—C7—C8	116.64 (14)	C19^i—C18—H18A	109.3
N1—C8—N4	111.09 (13)	C17A—C18—H18A	109.3
N1—C8—C7	109.99 (12)	C17B—C18—H18B	67.0
N4—C8—C7	113.31 (13)	C19^i—C18—H18B	109.3
N1—C8—H8A	107.4	C17A—C18—H18B	109.3
N4—C8—H8A	107.4	H18A—C18—H18B	108.0
C7—C8—H8A	107.4	C17B—C19—C17A	44.2 (6)
N1—C9—C14	103.81 (14)	C17B—C19—C18^i	115.1 (5)
N1—C9—C10	133.85 (15)	C17A—C19—C18^i	109.9 (5)
C14—C9—C10	122.34 (15)	C17B—C19—H19A	133.8
C11—C10—C9	115.56 (17)	C17A—C19—H19A	109.7
C11—C10—H10A	122.2	C18^i—C19—H19A	109.7
C9—C10—H10A	122.2	C17B—C19—H19B	66.8
C10—C11—C12	122.49 (18)	C17A—C19—H19B	109.7
C10—C11—H11A	118.8	C18^i—C19—H19B	109.7
C12—C11—H11A	118.8	H19A—C19—H19B	108.2
C13—C12—C11	121.73 (17)
C9—N1—N2—N3	0.07 (18)	C8—N1—C9—C14	179.59 (15)
C8—N1—N2—N3	−179.64 (14)	N2—N1—C9—C10	179.08 (17)
N1—N2—N3—C14	−0.03 (19)	C8—N1—C9—C10	−1.3 (3)
C15—N4—N6—C16	−0.6 (2)	N1—C9—C10—C11	−179.52 (17)
C8—N4—N6—C16	174.93 (17)	C14—C9—C10—C11	−0.5 (2)
C6—C1—C2—C3	−0.9 (3)	C9—C10—C11—C12	0.3 (3)
C1—C2—C3—C4	−0.2 (3)	C10—C11—C12—C13	0.0 (3)
C2—C3—C4—C5	1.2 (3)	C11—C12—C13—C14	−0.2 (3)
C3—C4—C5—C6	−1.0 (3)	N2—N3—C14—C9	0.0 (2)
C4—C5—C6—C1	−0.1 (3)	N2—N3—C14—C13	−179.48 (18)
C4—C5—C6—C7	179.92 (16)	N1—C9—C14—N3	0.05 (18)
C2—C1—C6—C5	1.0 (3)	C10—C9—C14—N3	−179.22 (15)
C2—C1—C6—C7	−178.97 (17)	N1—C9—C14—C13	179.58 (15)
C5—C6—C7—O1	160.50 (17)	C10—C9—C14—C13	0.3 (3)
C1—C6—C7—O1	−19.5 (2)	C12—C13—C14—N3	179.50 (18)
C5—C6—C7—C8	−20.1 (2)	C12—C13—C14—C9	0.1 (3)
C1—C6—C7—C8	159.89 (15)	C16—N5—C15—N4	0.2 (2)
N2—N1—C8—N4	−101.80 (15)	N6—N4—C15—N5	0.3 (2)
C9—N1—C8—N4	78.6 (2)	C8—N4—C15—N5	−174.88 (18)
N2—N1—C8—C7	131.94 (14)	N4—N6—C16—N5	0.7 (2)
C9—N1—C8—C7	−47.7 (2)	C15—N5—C16—N6	−0.6 (3)
C15—N4—C8—N1	125.48 (19)	C19—C17B—C18—C19^i	−40.3 (12)
N6—N4—C8—N1	−49.1 (2)	C19—C17B—C18—C17A	52.9 (6)
C15—N4—C8—C7	−110.1 (2)	C19—C17A—C18—C17B	−51.4 (6)
N6—N4—C8—C7	75.3 (2)	C19—C17A—C18—C19^i	56.1 (11)
O1—C7—C8—N1	118.30 (16)	C18—C17B—C19—C17A	−53.9 (8)
C6—C7—C8—N1	−61.13 (17)	C18—C17B—C19—C18^i	39.4 (12)
O1—C7—C8—N4	−6.7 (2)	C18—C17A—C19—C17B	50.8 (9)
C6—C7—C8—N4	173.87 (12)	C18—C17A—C19—C18^i	−55.2 (11)
N2—N1—C9—C14	−0.07 (17)

Symmetry code: (i) −x+1, −y−2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N5^ii	0.98	2.48	3.399 (2)	155
C16—H16A···N3^iii	0.93	2.57	3.489 (2)	172
C12—H12A···Cg3^iv	0.93	2.84	3.726	151

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