Download citation
Download citation
link to html
In the title mol­ecule, C27H22N6O, the dihedral angle between the two benzotriazole moieties is 18.2 (1)° and those between the central benzene ring and the attached benzotriazole moieties are 74.7 (1) and 88.3 (1)°. The molecular packing in the crystal structure is stabilized by intramolecular C—H...N hydrogen bonds and intermolecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027138/wn6299sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027138/wn6299Isup2.hkl
Contains datablock I

CCDC reference: 255952

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.130
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 27.99 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 5095 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5387 Completeness (_total/calc) 94.58% PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for C7 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C27 H22 N6 O
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 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

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Benzyl 3,5-bis(1H-benzotriazol-1-ylmethyl)phenyl ether top
Crystal data top
C27H22N6OF(000) = 936
Mr = 446.51Dx = 1.329 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4863 reflections
a = 8.5494 (9) Åθ = 2.3–27.1°
b = 9.5609 (10) ŵ = 0.09 mm1
c = 27.627 (3) ÅT = 293 K
β = 98.780 (2)°Block, colourless
V = 2231.8 (4) Å30.28 × 0.16 × 0.14 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3847 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 28.0°, θmin = 2.3°
ω scansh = 711
13153 measured reflectionsk = 1212
5095 independent reflectionsl = 3536
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0648P)2 + 0.3501P]
where P = (Fo2 + 2Fc2)/3
5095 reflections(Δ/σ)max < 0.001
307 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.24900 (17)0.38762 (16)0.24547 (5)0.0437 (3)
H10.30780.39250.21430.052*
C20.11705 (17)0.30081 (16)0.25415 (5)0.0425 (3)
C30.03168 (17)0.29322 (15)0.30041 (5)0.0418 (3)
H30.05670.23550.30630.050*
C40.07633 (17)0.37111 (14)0.33847 (5)0.0395 (3)
C50.20615 (17)0.45911 (15)0.32980 (5)0.0400 (3)
H50.23510.51280.35510.048*
C60.29294 (16)0.46661 (14)0.28305 (5)0.0373 (3)
C70.0596 (2)0.2137 (2)0.21448 (5)0.0651 (5)
H7A0.04550.24510.21040.078*
H7B0.05110.11700.22520.078*
C80.29272 (18)0.27637 (16)0.09726 (5)0.0441 (3)
C90.3411 (2)0.3578 (2)0.05562 (6)0.0607 (5)
H90.41840.32660.03060.073*
C100.2709 (3)0.4835 (2)0.05331 (7)0.0752 (6)
H100.30060.53990.02600.090*
C110.1554 (3)0.5310 (2)0.09063 (9)0.0794 (6)
H110.11160.61910.08770.095*
C120.1039 (2)0.45367 (19)0.13129 (7)0.0643 (5)
H120.02550.48550.15590.077*
C130.17597 (17)0.32371 (15)0.13371 (5)0.0412 (3)
C140.43529 (18)0.56300 (17)0.27563 (5)0.0492 (4)
H14A0.50100.54260.30040.059*
H14B0.39890.65880.28040.059*
C150.6332 (2)0.56075 (17)0.15099 (6)0.0535 (4)
C160.6576 (3)0.6103 (2)0.10278 (6)0.0711 (6)
H160.73280.57010.07900.085*
C170.5675 (3)0.7193 (2)0.09213 (6)0.0728 (6)
H170.58190.75440.06040.087*
C180.4536 (2)0.7805 (2)0.12741 (7)0.0663 (5)
H180.39360.85450.11840.080*
C190.4280 (2)0.73474 (17)0.17482 (6)0.0532 (4)
H190.35260.77580.19840.064*
C200.52089 (17)0.62330 (15)0.18589 (5)0.0418 (3)
C210.0221 (2)0.42788 (19)0.42365 (5)0.0586 (5)
H21A0.13290.41570.42650.070*
H21B0.00250.52670.41940.070*
C220.08034 (19)0.37432 (16)0.46888 (5)0.0473 (4)
C230.2305 (2)0.42702 (19)0.48294 (5)0.0543 (4)
H230.27020.49400.46370.065*
C240.3224 (2)0.3811 (2)0.52547 (6)0.0600 (4)
H240.42300.41820.53490.072*
C250.2656 (2)0.28076 (19)0.55380 (5)0.0592 (5)
H250.32760.24970.58240.071*
C260.1173 (2)0.22670 (19)0.53981 (6)0.0607 (5)
H260.07870.15830.55880.073*
C270.0253 (2)0.27352 (18)0.49761 (6)0.0554 (4)
H270.07550.23650.48840.066*
N10.16053 (15)0.22001 (13)0.16754 (4)0.0461 (3)
N20.26320 (18)0.11547 (14)0.15298 (5)0.0570 (4)
N30.34235 (18)0.14762 (15)0.11063 (5)0.0585 (4)
N40.53119 (14)0.55107 (13)0.22765 (4)0.0456 (3)
N50.64182 (17)0.44953 (16)0.21882 (6)0.0654 (4)
N60.70412 (19)0.45445 (17)0.17274 (6)0.0741 (5)
O10.01518 (13)0.35108 (12)0.38279 (3)0.0545 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0420 (8)0.0543 (9)0.0318 (6)0.0106 (7)0.0037 (5)0.0029 (6)
C20.0440 (8)0.0485 (8)0.0343 (6)0.0091 (7)0.0031 (6)0.0054 (6)
C30.0415 (8)0.0450 (8)0.0376 (7)0.0123 (6)0.0021 (6)0.0011 (6)
C40.0427 (8)0.0428 (8)0.0318 (6)0.0061 (6)0.0012 (5)0.0002 (5)
C50.0449 (8)0.0411 (8)0.0340 (6)0.0073 (6)0.0060 (6)0.0031 (5)
C60.0355 (7)0.0387 (7)0.0371 (6)0.0044 (6)0.0036 (5)0.0018 (5)
C70.0668 (11)0.0859 (13)0.0386 (8)0.0345 (10)0.0051 (7)0.0160 (8)
C80.0465 (8)0.0483 (8)0.0377 (7)0.0051 (7)0.0073 (6)0.0040 (6)
C90.0622 (11)0.0737 (12)0.0450 (8)0.0010 (9)0.0043 (7)0.0073 (8)
C100.0902 (15)0.0698 (13)0.0699 (12)0.0101 (12)0.0260 (11)0.0244 (10)
C110.0988 (16)0.0488 (11)0.0979 (15)0.0145 (11)0.0386 (13)0.0060 (10)
C120.0614 (11)0.0582 (11)0.0752 (12)0.0172 (9)0.0162 (9)0.0223 (9)
C130.0416 (8)0.0443 (8)0.0387 (7)0.0001 (6)0.0090 (6)0.0094 (6)
C140.0492 (9)0.0553 (9)0.0409 (7)0.0159 (7)0.0003 (6)0.0013 (6)
C150.0526 (9)0.0450 (9)0.0567 (9)0.0007 (7)0.0112 (7)0.0022 (7)
C160.0888 (14)0.0611 (11)0.0541 (10)0.0015 (10)0.0193 (9)0.0018 (8)
C170.1074 (16)0.0637 (12)0.0466 (9)0.0079 (11)0.0094 (10)0.0052 (8)
C180.0832 (13)0.0554 (11)0.0645 (10)0.0068 (10)0.0246 (10)0.0010 (8)
C190.0506 (9)0.0494 (9)0.0594 (9)0.0037 (8)0.0082 (7)0.0086 (7)
C200.0394 (7)0.0405 (8)0.0440 (7)0.0088 (6)0.0015 (6)0.0007 (6)
C210.0685 (11)0.0687 (11)0.0352 (7)0.0283 (9)0.0031 (7)0.0107 (7)
C220.0554 (9)0.0534 (9)0.0316 (6)0.0192 (7)0.0016 (6)0.0080 (6)
C230.0565 (10)0.0613 (10)0.0452 (8)0.0089 (8)0.0075 (7)0.0071 (7)
C240.0495 (9)0.0737 (12)0.0532 (9)0.0099 (9)0.0039 (7)0.0021 (8)
C250.0675 (11)0.0691 (11)0.0384 (7)0.0261 (9)0.0001 (7)0.0051 (7)
C260.0774 (13)0.0567 (10)0.0504 (9)0.0115 (9)0.0171 (8)0.0083 (7)
C270.0561 (10)0.0573 (10)0.0518 (9)0.0051 (8)0.0050 (7)0.0094 (7)
N10.0519 (7)0.0507 (7)0.0342 (6)0.0078 (6)0.0021 (5)0.0096 (5)
N20.0751 (10)0.0490 (8)0.0463 (7)0.0047 (7)0.0067 (7)0.0013 (6)
N30.0698 (9)0.0555 (8)0.0467 (7)0.0181 (7)0.0019 (6)0.0023 (6)
N40.0368 (6)0.0465 (7)0.0506 (7)0.0072 (6)0.0023 (5)0.0054 (5)
N50.0515 (8)0.0609 (9)0.0783 (10)0.0064 (7)0.0072 (7)0.0204 (8)
N60.0636 (10)0.0641 (10)0.0836 (11)0.0159 (8)0.0243 (8)0.0162 (8)
O10.0613 (7)0.0673 (7)0.0312 (5)0.0278 (6)0.0045 (4)0.0066 (5)
Geometric parameters (Å, º) top
C1—C61.3815 (19)C15—C201.388 (2)
C1—C21.392 (2)C15—C161.399 (2)
C1—H10.9300C16—C171.354 (3)
C2—C31.3736 (18)C16—H160.9300
C2—C71.517 (2)C17—C181.397 (3)
C3—C41.3886 (19)C17—H170.9300
C3—H30.9300C18—C191.366 (2)
C4—O11.3624 (15)C18—H180.9300
C4—C51.384 (2)C19—C201.391 (2)
C5—C61.3896 (17)C19—H190.9300
C5—H50.9300C20—N41.359 (2)
C6—C141.515 (2)C21—O11.423 (2)
C7—N11.4450 (18)C21—C221.502 (2)
C7—H7A0.9700C21—H21A0.9700
C7—H7B0.9700C21—H21B0.9700
C8—N31.371 (2)C22—C271.377 (2)
C8—C131.381 (2)C22—C231.379 (2)
C8—C91.398 (2)C23—C241.382 (2)
C9—C101.350 (3)C23—H230.9300
C9—H90.9300C24—C251.373 (3)
C10—C111.391 (3)C24—H240.9300
C10—H100.9300C25—C261.369 (3)
C11—C121.361 (3)C25—H250.9300
C11—H110.9300C26—C271.378 (2)
C12—C131.393 (2)C26—H260.9300
C12—H120.9300C27—H270.9300
C13—N11.355 (2)N1—N21.350 (2)
C14—N41.453 (2)N2—N31.296 (2)
C14—H14A0.9700N4—N51.351 (2)
C14—H14B0.9700N5—N61.304 (2)
C15—N61.369 (2)
C6—C1—C2120.19 (12)C17—C16—C15117.40 (16)
C6—C1—H1119.9C17—C16—H16121.3
C2—C1—H1119.9C15—C16—H16121.3
C3—C2—C1119.57 (12)C16—C17—C18121.99 (17)
C3—C2—C7117.31 (13)C16—C17—H17119.0
C1—C2—C7123.12 (12)C18—C17—H17119.0
C2—C3—C4120.51 (13)C19—C18—C17121.83 (18)
C2—C3—H3119.7C19—C18—H18119.1
C4—C3—H3119.7C17—C18—H18119.1
O1—C4—C5125.19 (12)C18—C19—C20116.29 (15)
O1—C4—C3114.75 (12)C18—C19—H19121.9
C5—C4—C3120.06 (12)C20—C19—H19121.9
C4—C5—C6119.50 (12)N4—C20—C15104.08 (14)
C4—C5—H5120.3N4—C20—C19133.58 (14)
C6—C5—H5120.3C15—C20—C19122.34 (14)
C1—C6—C5120.16 (12)O1—C21—C22108.14 (12)
C1—C6—C14122.39 (12)O1—C21—H21A110.1
C5—C6—C14117.45 (12)C22—C21—H21A110.1
N1—C7—C2114.26 (13)O1—C21—H21B110.1
N1—C7—H7A108.7C22—C21—H21B110.1
C2—C7—H7A108.7H21A—C21—H21B108.4
N1—C7—H7B108.7C27—C22—C23118.63 (14)
C2—C7—H7B108.7C27—C22—C21120.74 (16)
H7A—C7—H7B107.6C23—C22—C21120.62 (16)
N3—C8—C13108.47 (13)C22—C23—C24120.51 (16)
N3—C8—C9131.03 (14)C22—C23—H23119.7
C13—C8—C9120.50 (15)C24—C23—H23119.7
C10—C9—C8117.18 (17)C25—C24—C23120.14 (17)
C10—C9—H9121.4C25—C24—H24119.9
C8—C9—H9121.4C23—C24—H24119.9
C9—C10—C11121.78 (18)C26—C25—C24119.73 (15)
C9—C10—H10119.1C26—C25—H25120.1
C11—C10—H10119.1C24—C25—H25120.1
C12—C11—C10122.55 (18)C25—C26—C27120.06 (17)
C12—C11—H11118.7C25—C26—H26120.0
C10—C11—H11118.7C27—C26—H26120.0
C11—C12—C13115.76 (17)C22—C27—C26120.92 (16)
C11—C12—H12122.1C22—C27—H27119.5
C13—C12—H12122.1C26—C27—H27119.5
N1—C13—C8104.27 (13)N2—N1—C13110.22 (11)
N1—C13—C12133.51 (15)N2—N1—C7120.6 (1)
C8—C13—C12122.21 (15)C13—N1—C7129.2 (1)
N4—C14—C6113.92 (12)N3—N2—N1108.64 (12)
N4—C14—H14A108.8N2—N3—C8108.40 (12)
C6—C14—H14A108.8N5—N4—C20110.24 (12)
N4—C14—H14B108.8N5—N4—C14120.2 (1)
C6—C14—H14B108.8C20—N4—C14129.4 (1)
H14A—C14—H14B107.7N6—N5—N4108.71 (13)
N6—C15—C20108.70 (14)N5—N6—C15108.26 (13)
N6—C15—C16131.16 (16)C4—O1—C21118.24 (11)
C20—C15—C16120.15 (16)
C6—C1—C2—C30.6 (2)C18—C19—C20—C150.3 (2)
C6—C1—C2—C7178.57 (16)O1—C21—C22—C2795.25 (18)
C1—C2—C3—C40.2 (2)O1—C21—C22—C2385.93 (19)
C7—C2—C3—C4179.38 (15)C27—C22—C23—C241.1 (2)
C2—C3—C4—O1178.12 (14)C21—C22—C23—C24177.76 (14)
C2—C3—C4—C51.1 (2)C22—C23—C24—C250.9 (3)
O1—C4—C5—C6177.85 (13)C23—C24—C25—C260.2 (3)
C3—C4—C5—C61.3 (2)C24—C25—C26—C270.4 (3)
C2—C1—C6—C50.4 (2)C23—C22—C27—C260.5 (2)
C2—C1—C6—C14179.89 (15)C21—C22—C27—C26178.32 (14)
C4—C5—C6—C10.5 (2)C25—C26—C27—C220.2 (3)
C4—C5—C6—C14179.18 (14)C8—C13—N1—N20.63 (16)
C3—C2—C7—N1176.3 (2)C12—C13—N1—N2177.89 (17)
C1—C2—C7—N14.5 (3)C8—C13—N1—C7177.59 (14)
N3—C8—C9—C10178.72 (18)C12—C13—N1—C70.9 (3)
C13—C8—C9—C101.0 (2)C2—C7—N1—N2100.70 (18)
C8—C9—C10—C110.1 (3)C2—C7—N1—C1376.0 (2)
C9—C10—C11—C121.1 (3)C13—N1—N2—N30.93 (17)
C10—C11—C12—C130.9 (3)C7—N1—N2—N3178.19 (13)
N3—C8—C13—N10.14 (16)N1—N2—N3—C80.82 (18)
C9—C8—C13—N1179.91 (14)C13—C8—N3—N20.42 (18)
N3—C8—C13—C12178.60 (15)C9—C8—N3—N2179.31 (17)
C9—C8—C13—C121.2 (2)C15—C20—N4—N50.60 (17)
C11—C12—C13—N1178.51 (17)C19—C20—N4—N5179.62 (16)
C11—C12—C13—C80.2 (2)C15—C20—N4—C14175.41 (14)
C1—C6—C14—N47.4 (2)C19—C20—N4—C144.8 (3)
C5—C6—C14—N4172.34 (13)C6—C14—N4—N583.39 (18)
N6—C15—C16—C17180.0 (2)C6—C14—N4—C2090.97 (18)
C20—C15—C16—C170.4 (3)C20—N4—N5—N60.43 (19)
C15—C16—C17—C180.3 (3)C14—N4—N5—N6175.79 (14)
C16—C17—C18—C190.7 (3)N4—N5—N6—C150.1 (2)
C17—C18—C19—C200.4 (3)C20—C15—N6—N50.3 (2)
N6—C15—C20—N40.56 (18)C16—C15—N6—N5179.28 (19)
C16—C15—C20—N4179.10 (16)C5—C4—O1—C211.3 (2)
N6—C15—C20—C19179.63 (15)C3—C4—O1—C21179.54 (15)
C16—C15—C20—C190.7 (2)C22—C21—O1—C4172.6 (1)
C18—C19—C20—N4179.44 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···N10.932.542.876 (2)102
C1—H1···N40.932.512.854 (2)102
C11—H11···O1i0.932.463.327 (2)155
Symmetry code: (i) x, y+1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds