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In the mol­ecule of the title compound, C23H16Cl2N4, the dihedral angle between the benzene rings fused to the azepine ring is 52.00 (6)°. The plane of the triazole ring makes dihedral angles of 74.40 (5), 25.56 (8) and 44.78 (6)° with the planes of the benzene rings of the dibenzoazepine moiety and the di­chloro­phenyl ring, respectively. The azepine ring adopts a boat conformation. There are no classical hydrogen bonds in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314616002212/pk4001sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314616002212/pk4001Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314616002212/pk4001Isup3.cml
Supplementary material

CCDC reference: 1451830

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.091
  • Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5860 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.974 Note PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.586 83 Report PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 1 Check
Alert level G PLAT005_ALERT_5_G No Embedded Refinement Details found in the CIF Please Do ! PLAT008_ALERT_5_G No _iucr_refine_reflections_details in the CIF Please Do ! PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still 89 % PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 9 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 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 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

5-{[1-(2,4-Dichlorophenyl)-1H-1,2,3-triazol-4-yl]methyl}-5H-dibenz[b,f]azepine top
Crystal data top
C23H16Cl2N4F(000) = 1728
Mr = 419.30Dx = 1.427 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 3210 reflections
a = 13.2330 (11) Åθ = 4.3–64.6°
b = 8.7515 (7) ŵ = 3.13 mm1
c = 33.695 (3) ÅT = 296 K
V = 3902.2 (6) Å3Block, light yellow
Z = 80.29 × 0.26 × 0.23 mm
Data collection top
Bruker X8 Proteum
diffractometer
3210 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode3089 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.041
Detector resolution: 10.7 pixels mm-1θmax = 64.6°, θmin = 4.3°
φ and ω scansh = 1315
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 108
Tmin = 0.464, Tmax = 0.533l = 3838
20100 measured reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0531P)2 + 1.9833P]
where P = (Fo2 + 2Fc2)/3
3210 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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
Cl280.53010 (3)0.65530 (5)0.53902 (1)0.0260 (1)
Cl290.63027 (3)1.03517 (5)0.42010 (1)0.0302 (2)
N10.66079 (10)0.58214 (15)0.67786 (4)0.0182 (4)
N180.84679 (10)0.53348 (14)0.59627 (4)0.0193 (4)
N190.83790 (10)0.59721 (15)0.56132 (4)0.0193 (4)
N200.75208 (10)0.68295 (14)0.56223 (4)0.0170 (3)
C20.57186 (12)0.52280 (17)0.65898 (4)0.0181 (4)
C30.57308 (12)0.38226 (18)0.63960 (5)0.0205 (5)
C40.48933 (13)0.32968 (19)0.61912 (5)0.0241 (5)
C50.40285 (13)0.4183 (2)0.61745 (5)0.0260 (5)
C60.40111 (13)0.5588 (2)0.63632 (5)0.0255 (5)
C70.48426 (12)0.61320 (19)0.65786 (5)0.0212 (5)
C80.47687 (13)0.7600 (2)0.67837 (5)0.0261 (5)
C90.52101 (13)0.79772 (19)0.71276 (5)0.0256 (5)
C100.58799 (12)0.70227 (18)0.73680 (5)0.0209 (5)
C110.58832 (13)0.72054 (19)0.77811 (5)0.0254 (5)
C120.65044 (14)0.6344 (2)0.80224 (5)0.0264 (5)
C130.71444 (13)0.52698 (19)0.78552 (5)0.0247 (5)
C140.71582 (12)0.50611 (19)0.74478 (5)0.0211 (5)
C150.65428 (12)0.59383 (17)0.72018 (5)0.0184 (5)
C160.75821 (12)0.53003 (17)0.66218 (4)0.0184 (5)
C170.76794 (11)0.57852 (17)0.61969 (4)0.0172 (4)
C210.70728 (12)0.67415 (17)0.59844 (4)0.0175 (4)
C220.72075 (12)0.76532 (17)0.52791 (4)0.0177 (4)
C230.79272 (12)0.84767 (18)0.50702 (5)0.0207 (5)
C240.76590 (13)0.92902 (19)0.47349 (5)0.0225 (5)
C250.66572 (13)0.92946 (19)0.46149 (4)0.0218 (5)
C260.59215 (13)0.84824 (18)0.48186 (5)0.0214 (5)
C270.62067 (12)0.76384 (18)0.51495 (5)0.0192 (5)
H30.631200.322600.640400.0250*
H40.491200.235100.606500.0290*
H50.346300.383800.603700.0310*
H60.343200.618700.634700.0310*
H80.437500.834800.666300.0310*
H90.507600.895200.722400.0310*
H110.545600.792500.789600.0300*
H120.649300.648400.829600.0320*
H130.756500.468800.801700.0300*
H140.758200.432800.733700.0250*
H16A0.762600.419600.664000.0220*
H16B0.812800.573700.677700.0220*
H210.648500.722500.606800.0210*
H230.859500.848100.515600.0250*
H240.814400.982700.459200.0270*
H260.525100.850200.473500.0260*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl280.0191 (2)0.0327 (3)0.0262 (2)0.0071 (2)0.0001 (2)0.0035 (2)
Cl290.0328 (3)0.0320 (3)0.0257 (2)0.0015 (2)0.0065 (2)0.0086 (2)
N10.0192 (7)0.0194 (7)0.0159 (6)0.0014 (5)0.0018 (5)0.0003 (5)
N180.0187 (7)0.0192 (7)0.0200 (7)0.0003 (5)0.0020 (5)0.0005 (5)
N190.0182 (7)0.0197 (7)0.0200 (7)0.0015 (5)0.0013 (5)0.0008 (5)
N200.0165 (6)0.0174 (6)0.0170 (6)0.0005 (5)0.0015 (5)0.0008 (5)
C20.0192 (8)0.0205 (8)0.0146 (7)0.0003 (6)0.0033 (6)0.0041 (6)
C30.0226 (8)0.0205 (8)0.0185 (8)0.0003 (7)0.0033 (6)0.0015 (6)
C40.0280 (9)0.0257 (9)0.0187 (8)0.0062 (7)0.0021 (7)0.0008 (6)
C50.0248 (9)0.0343 (10)0.0188 (8)0.0073 (7)0.0013 (7)0.0051 (7)
C60.0196 (8)0.0339 (9)0.0229 (8)0.0035 (7)0.0022 (7)0.0086 (7)
C70.0231 (8)0.0233 (8)0.0172 (8)0.0021 (7)0.0043 (6)0.0052 (6)
C80.0276 (9)0.0243 (9)0.0263 (9)0.0092 (7)0.0039 (7)0.0047 (7)
C90.0313 (9)0.0188 (8)0.0267 (9)0.0068 (7)0.0073 (7)0.0009 (7)
C100.0247 (8)0.0164 (8)0.0216 (8)0.0023 (6)0.0036 (6)0.0015 (6)
C110.0316 (9)0.0202 (8)0.0244 (8)0.0012 (7)0.0061 (7)0.0056 (7)
C120.0358 (10)0.0266 (9)0.0168 (8)0.0054 (7)0.0007 (7)0.0037 (7)
C130.0290 (9)0.0242 (9)0.0210 (8)0.0015 (7)0.0033 (7)0.0008 (6)
C140.0236 (8)0.0185 (8)0.0212 (8)0.0006 (6)0.0002 (6)0.0013 (6)
C150.0224 (8)0.0155 (8)0.0174 (8)0.0036 (6)0.0019 (6)0.0010 (6)
C160.0195 (8)0.0171 (8)0.0186 (8)0.0020 (6)0.0008 (6)0.0003 (6)
C170.0176 (8)0.0147 (7)0.0193 (8)0.0021 (6)0.0014 (6)0.0029 (6)
C210.0196 (8)0.0165 (7)0.0165 (7)0.0013 (6)0.0028 (6)0.0022 (6)
C220.0211 (8)0.0164 (7)0.0156 (7)0.0008 (6)0.0017 (6)0.0028 (6)
C230.0191 (8)0.0221 (8)0.0210 (8)0.0005 (6)0.0008 (6)0.0017 (6)
C240.0244 (9)0.0227 (8)0.0203 (8)0.0021 (6)0.0033 (7)0.0008 (6)
C250.0283 (9)0.0195 (8)0.0177 (8)0.0009 (7)0.0015 (6)0.0009 (6)
C260.0194 (8)0.0234 (8)0.0215 (8)0.0002 (6)0.0022 (6)0.0038 (6)
C270.0191 (8)0.0195 (8)0.0191 (8)0.0016 (6)0.0020 (6)0.0034 (6)
Geometric parameters (Å, º) top
C2—C31.393 (2)C24—C251.386 (2)
C2—C71.404 (2)C25—C261.387 (2)
C3—C41.384 (2)C26—C271.390 (2)
C4—C51.384 (2)C3—H30.9300
C5—C61.384 (2)C4—H40.9300
C6—C71.402 (2)C5—H50.9300
C7—C81.462 (2)C6—H60.9300
C8—C91.339 (2)C8—H80.9300
C9—C101.463 (2)C9—H90.9300
C10—C111.401 (2)C11—H110.9300
C10—C151.409 (2)C12—H120.9300
C11—C121.380 (2)C13—H130.9300
C12—C131.385 (2)C14—H140.9300
C13—C141.385 (2)C16—H16A0.9700
C14—C151.393 (2)C16—H16B0.9700
C16—C171.4988 (19)C21—H210.9300
C17—C211.363 (2)C23—H230.9300
C22—C231.386 (2)C24—H240.9300
C22—C271.395 (2)C26—H260.9300
C23—C241.382 (2)
Cl28···N203.0494 (14)C13···H8vi3.0800
Cl28···C213.0876 (16)C14···H16B2.6700
Cl28···C23i3.5035 (17)C14···H16A2.8900
Cl28···C24i3.5980 (18)C16···H32.5800
Cl28···H212.8300C16···H142.5600
Cl28···H23i2.9100C16···H3v3.0400
Cl28···H24i3.1000C17···H3v2.6100
Cl29···H5ii3.0500C17···H32.9600
Cl29···H4iii3.0000C21···H3v2.8700
N18···C21iv3.226 (2)H3···C162.5800
N18···C22iv3.408 (2)H3···C172.9600
N19···C27iv3.355 (2)H3···H16A2.0900
N19···C23iv3.332 (2)H3···N18iv2.9500
N19···C22iv3.210 (2)H3···C16iv3.0400
N20···Cl283.0494 (14)H3···C17iv2.6100
N1···H212.7000H3···C21iv2.8700
N18···H3v2.9500H4···Cl29iii3.0000
N18···H21iv2.7500H4···N18iv2.8000
N18···H4v2.8000H5···Cl29i3.0500
N19···H232.7000H5···H24i2.4600
N19···H26ii2.7800H6···H82.5000
C2···C213.021 (2)H8···H62.5000
C3···C213.406 (2)H8···C12viii3.0600
C3···C173.170 (2)H8···C13viii3.0800
C3···C17iv3.456 (2)H9···H112.4900
C17···C33.170 (2)H9···C12viii3.0700
C17···C3v3.456 (2)H11···H92.4900
C21···Cl283.0876 (16)H11···C2viii3.0800
C21···N18v3.226 (2)H11···C3viii2.9600
C21···C23.021 (2)H12···C4viii2.9800
C21···C33.406 (2)H12···C5viii3.0400
C22···C24iv3.472 (2)H13···C6ix2.9400
C22···N19v3.210 (2)H13···C11iv3.0900
C22···N18v3.408 (2)H14···C162.5600
C23···Cl28ii3.5035 (17)H14···H16A2.3500
C23···N19v3.332 (2)H14···H16B2.3700
C24···C22v3.472 (2)H14···C10iv2.8700
C24···C27v3.576 (2)H16A···C32.6600
C24···Cl28ii3.5980 (18)H16A···C142.8900
C27···N19v3.355 (2)H16A···H32.0900
C27···C24iv3.576 (2)H16A···H142.3500
C2···H11vi3.0800H16B···C142.6700
C2···H212.6800H16B···H142.3700
C3···H11vi2.9600H21···Cl282.8300
C3···H16A2.6600H21···N12.7000
C4···H12vi2.9800H21···C22.6800
C5···H24i2.9600H21···C72.9300
C5···H12vi3.0400H21···N18v2.7500
C6···H13vii2.9400H23···N192.7000
C7···H212.9300H23···Cl28ii2.9100
C10···H14v2.8700H24···Cl28ii3.1000
C11···H13v3.0900H24···C5ii2.9600
C12···H9vi3.0700H24···H5ii2.4600
C12···H8vi3.0600H26···N19i2.7800
C3—C2—C7119.65 (14)C4—C5—H5120.00
C2—C3—C4121.20 (15)C6—C5—H5120.00
C3—C4—C5119.75 (15)C5—C6—H6119.00
C4—C5—C6119.53 (16)C7—C6—H6119.00
C5—C6—C7121.77 (16)C7—C8—H8117.00
C2—C7—C6118.08 (15)C9—C8—H8117.00
C2—C7—C8122.53 (15)C8—C9—H9116.00
C6—C7—C8119.39 (15)C10—C9—H9116.00
C7—C8—C9126.62 (16)C10—C11—H11119.00
C8—C9—C10127.07 (16)C12—C11—H11119.00
C9—C10—C11119.14 (15)C11—C12—H12120.00
C9—C10—C15122.82 (15)C13—C12—H12120.00
C11—C10—C15118.03 (15)C12—C13—H13120.00
C10—C11—C12121.65 (16)C14—C13—H13120.00
C11—C12—C13119.69 (16)C13—C14—H14120.00
C12—C13—C14120.05 (16)C15—C14—H14120.00
C13—C14—C15120.63 (15)N1—C16—H16A110.00
C10—C15—C14119.93 (15)N1—C16—H16B110.00
C16—C17—C21128.69 (13)C17—C16—H16A110.00
C23—C22—C27119.88 (14)C17—C16—H16B110.00
C22—C23—C24120.43 (15)H16A—C16—H16B108.00
C23—C24—C25119.06 (15)N20—C21—H21128.00
C24—C25—C26121.70 (14)C17—C21—H21128.00
C25—C26—C27118.60 (15)C22—C23—H23120.00
C22—C27—C26120.28 (15)C24—C23—H23120.00
C2—C3—H3119.00C23—C24—H24120.00
C4—C3—H3119.00C25—C24—H24121.00
C3—C4—H4120.00C25—C26—H26121.00
C5—C4—H4120.00C27—C26—H26121.00
C15—N1—C2—C3113.85 (16)C6—C7—C8—C9146.28 (18)
C15—N1—C2—C770.45 (18)C7—C8—C9—C101.6 (3)
C16—N1—C2—C326.1 (2)C8—C9—C10—C11148.74 (18)
C16—N1—C2—C7149.60 (14)C8—C9—C10—C1532.6 (3)
C2—N1—C15—C1068.50 (18)C9—C10—C11—C12179.55 (16)
C2—N1—C15—C14114.92 (16)C15—C10—C11—C120.8 (2)
C16—N1—C15—C10151.16 (14)C9—C10—C15—N13.6 (2)
C16—N1—C15—C1425.4 (2)C9—C10—C15—C14179.74 (15)
C2—N1—C16—C1761.72 (16)C11—C10—C15—N1175.10 (14)
C15—N1—C16—C17158.73 (12)C11—C10—C15—C141.5 (2)
C17—N18—N19—N200.49 (16)C10—C11—C12—C130.1 (3)
N19—N18—C17—C16177.60 (13)C11—C12—C13—C140.1 (3)
N19—N18—C17—C210.09 (18)C12—C13—C14—C150.9 (3)
N18—N19—N20—C210.74 (16)C13—C14—C15—N1174.92 (15)
N18—N19—N20—C22178.99 (12)C13—C14—C15—C101.6 (2)
N19—N20—C21—C170.66 (16)N1—C16—C17—N18173.67 (13)
C22—N20—C21—C17179.03 (14)N1—C16—C17—C219.1 (2)
N19—N20—C22—C2345.0 (2)N18—C17—C21—N200.35 (16)
N19—N20—C22—C27134.51 (15)C16—C17—C21—N20177.85 (14)
C21—N20—C22—C23135.31 (16)N20—C22—C23—C24179.84 (14)
C21—N20—C22—C2745.2 (2)C27—C22—C23—C240.3 (2)
N1—C2—C3—C4175.61 (15)N20—C22—C27—Cl282.5 (2)
C7—C2—C3—C40.1 (2)N20—C22—C27—C26178.54 (14)
N1—C2—C7—C6174.54 (14)C23—C22—C27—Cl28177.04 (12)
N1—C2—C7—C85.8 (2)C23—C22—C27—C261.9 (2)
C3—C2—C7—C61.2 (2)C22—C23—C24—C251.2 (2)
C3—C2—C7—C8178.41 (15)C23—C24—C25—Cl29178.38 (13)
C2—C3—C4—C50.6 (3)C23—C24—C25—C261.2 (2)
C3—C4—C5—C60.0 (2)Cl29—C25—C26—C27180.00 (13)
C4—C5—C6—C71.2 (3)C24—C25—C26—C270.5 (2)
C5—C6—C7—C21.8 (2)C25—C26—C27—Cl28177.01 (12)
C5—C6—C7—C8177.82 (16)C25—C26—C27—C222.0 (2)
C2—C7—C8—C933.4 (3)
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x+1/2, y+3/2, z+1; (iii) x+1, y+1, z+1; (iv) x+3/2, y1/2, z; (v) x+3/2, y+1/2, z; (vi) x+1, y1/2, z+3/2; (vii) x1/2, y, z+3/2; (viii) x+1, y+1/2, z+3/2; (ix) x+1/2, y, z+3/2.
 

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