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The ester mol­ecule of the title compound, C13H11ClN2O2·C6H6, is not planar, with a dihedral angle between the benzene and pyridine rings of 15.2 (3)°. Two ester mol­ecules are connected by inter­molecular N—H...N hydrogen bonds, forming a dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007921/at2227sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007921/at2227Isup2.hkl
Contains datablock I

CCDC reference: 640249

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.048
  • wR factor = 0.138
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

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Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.290 0.340 Tmin(prime) and Tmax expected: 0.916 0.964 RR(prime) = 0.897 Please check that your absorption correction is appropriate. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 2.83 PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 500 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H1N ... ?
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 2.834 Tmax scaled 0.964 Tmin scaled 0.822 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 9 ALERT level C = Check and explain 3 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 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

6-Chloro-3-pyridylmethyl 4-aminobenzoate benzene solvate top
Crystal data top
C13H11ClN2O2·C6H6F(000) = 1424
Mr = 340.80Dx = 1.296 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2ycCell parameters from 1755 reflections
a = 20.688 (5) Åθ = 1.5–28.3°
b = 6.289 (5) ŵ = 0.23 mm1
c = 26.845 (5) ÅT = 293 K
β = 90.799 (5)°Block, yellow
V = 3492 (3) Å30.37 × 0.21 × 0.16 mm
Z = 8
Data collection top
Bruker APEX CCD area-detector
diffractometer
4056 independent reflections
Radiation source: fine-focus sealed tube1774 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2724
Tmin = 0.29, Tmax = 0.34k = 88
10258 measured reflectionsl = 3520
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 0.94 w = 1/[σ2(Fo2) + (0.0548P)2]
where P = (Fo2 + 2Fc2)/3
4056 reflections(Δ/σ)max = 0.001
223 parametersΔρmax = 0.15 e Å3
6 restraintsΔρmin = 0.17 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
C10.3137 (2)0.3905 (7)0.72658 (18)0.1229 (14)
H10.28330.28420.72070.148*
C20.3648 (3)0.3552 (6)0.75936 (16)0.1249 (14)
H20.36880.22600.77600.150*
C30.40959 (18)0.5145 (7)0.76695 (14)0.1099 (12)
H30.44460.49260.78840.132*
C40.40249 (16)0.7028 (6)0.74314 (13)0.0959 (10)
H40.43240.81080.74880.115*
C50.35246 (17)0.7359 (6)0.71124 (12)0.0956 (10)
H50.34860.86570.69490.115*
C60.30798 (17)0.5820 (7)0.70289 (15)0.1089 (12)
H60.27350.60640.68100.131*
C70.49449 (13)0.7476 (4)0.37435 (9)0.0625 (7)
C80.54091 (12)0.5946 (4)0.38159 (10)0.0665 (7)
H80.58050.60250.36570.080*
C90.52690 (12)0.4298 (4)0.41292 (10)0.0662 (7)
H90.55730.32330.41870.079*
C100.46751 (11)0.4215 (3)0.43607 (9)0.0543 (6)
C110.42479 (12)0.5845 (4)0.42567 (10)0.0653 (7)
H110.38470.58080.44080.078*
C120.45169 (11)0.2392 (4)0.46951 (10)0.0652 (7)
H12A0.44390.11210.44990.078*
H12B0.48760.21180.49220.078*
C130.37215 (12)0.1385 (4)0.52713 (10)0.0621 (7)
C140.31548 (11)0.2063 (4)0.55505 (9)0.0575 (6)
C150.28871 (12)0.0665 (4)0.58908 (10)0.0678 (7)
H150.30730.06690.59360.081*
C160.23542 (13)0.1210 (4)0.61612 (11)0.0714 (8)
H160.21860.02520.63890.086*
C170.20634 (12)0.3198 (4)0.60955 (10)0.0654 (7)
C180.23273 (12)0.4592 (4)0.57552 (10)0.0661 (7)
H180.21380.59180.57060.079*
C190.28644 (12)0.4048 (4)0.54892 (10)0.0626 (7)
H190.30370.50150.52650.075*
N10.43721 (10)0.7473 (3)0.39525 (8)0.0683 (6)
O10.39706 (9)0.0343 (3)0.52974 (8)0.0891 (7)
O20.39484 (7)0.2923 (3)0.49716 (6)0.0636 (5)
Cl10.50998 (4)0.96069 (12)0.33530 (3)0.0927 (3)
N20.15393 (13)0.3764 (5)0.63745 (11)0.0903 (9)
H1N0.1354 (16)0.276 (6)0.6575 (13)0.136*
H2N0.1336 (18)0.480 (6)0.6299 (15)0.136*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.132 (4)0.110 (3)0.127 (4)0.047 (3)0.011 (3)0.025 (3)
C20.183 (4)0.082 (3)0.111 (3)0.006 (3)0.029 (3)0.018 (2)
C30.100 (3)0.136 (3)0.093 (3)0.011 (3)0.007 (2)0.022 (3)
C40.095 (2)0.115 (3)0.078 (2)0.026 (2)0.005 (2)0.009 (2)
C50.107 (3)0.092 (2)0.088 (2)0.001 (2)0.009 (2)0.004 (2)
C60.084 (2)0.128 (3)0.114 (3)0.000 (2)0.016 (2)0.010 (3)
C70.0705 (17)0.0529 (15)0.0643 (17)0.0000 (13)0.0020 (15)0.0029 (13)
C80.0587 (15)0.0682 (18)0.0729 (18)0.0060 (13)0.0080 (14)0.0040 (15)
C90.0605 (16)0.0642 (17)0.0737 (19)0.0153 (13)0.0003 (15)0.0045 (15)
C100.0572 (15)0.0454 (14)0.0601 (16)0.0065 (11)0.0025 (13)0.0073 (12)
C110.0604 (15)0.0591 (16)0.0766 (19)0.0114 (13)0.0107 (14)0.0050 (14)
C120.0648 (16)0.0570 (16)0.0740 (18)0.0151 (13)0.0066 (14)0.0006 (14)
C130.0643 (16)0.0552 (16)0.0665 (18)0.0080 (13)0.0053 (14)0.0049 (14)
C140.0601 (15)0.0523 (15)0.0598 (16)0.0071 (12)0.0076 (13)0.0036 (13)
C150.0658 (17)0.0567 (16)0.081 (2)0.0102 (13)0.0023 (16)0.0102 (15)
C160.0675 (17)0.0683 (18)0.079 (2)0.0022 (14)0.0020 (15)0.0155 (15)
C170.0574 (16)0.0716 (18)0.0672 (18)0.0080 (13)0.0019 (14)0.0018 (15)
C180.0686 (17)0.0538 (15)0.0760 (19)0.0138 (13)0.0004 (15)0.0050 (14)
C190.0649 (16)0.0559 (16)0.0670 (17)0.0066 (12)0.0010 (14)0.0054 (13)
N10.0683 (14)0.0589 (14)0.0780 (16)0.0109 (11)0.0110 (12)0.0092 (12)
O10.0892 (13)0.0625 (12)0.1162 (17)0.0284 (10)0.0210 (12)0.0241 (11)
O20.0661 (11)0.0536 (10)0.0712 (12)0.0114 (8)0.0072 (9)0.0041 (9)
Cl10.1002 (6)0.0746 (5)0.1039 (7)0.0004 (4)0.0211 (5)0.0202 (4)
N20.0773 (18)0.091 (2)0.103 (2)0.0173 (14)0.0183 (16)0.0109 (17)
Geometric parameters (Å, º) top
C1—C61.366 (5)C11—N11.337 (3)
C1—C21.384 (5)C11—H110.9300
C1—H10.9300C12—O21.439 (3)
C2—C31.379 (5)C12—H12A0.9700
C2—H20.9300C12—H12B0.9700
C3—C41.353 (4)C13—O11.204 (3)
C3—H30.9300C13—O21.347 (3)
C4—C51.350 (4)C13—C141.464 (3)
C4—H40.9300C14—C151.389 (3)
C5—C61.352 (4)C14—C191.394 (3)
C5—H50.9300C15—C161.372 (3)
C6—H60.9300C15—H150.9300
C7—N11.318 (3)C16—C171.398 (4)
C7—C81.372 (3)C16—H160.9300
C7—Cl11.734 (3)C17—N21.373 (3)
C8—C91.368 (4)C17—C181.384 (4)
C8—H80.9300C18—C191.372 (3)
C9—C101.386 (3)C18—H180.9300
C9—H90.9300C19—H190.9300
C10—C111.379 (3)N2—H1N0.92 (4)
C10—C121.495 (3)N2—H2N0.80 (4)
C6—C1—C2119.9 (4)O2—C12—C10108.62 (19)
C6—C1—H1120.1O2—C12—H12A110.0
C2—C1—H1120.1C10—C12—H12A110.0
C3—C2—C1118.9 (4)O2—C12—H12B110.0
C3—C2—H2120.6C10—C12—H12B110.0
C1—C2—H2120.6H12A—C12—H12B108.3
C4—C3—C2119.9 (4)O1—C13—O2122.0 (2)
C4—C3—H3120.1O1—C13—C14125.3 (2)
C2—C3—H3120.1O2—C13—C14112.6 (2)
C5—C4—C3120.8 (3)C15—C14—C19118.0 (2)
C5—C4—H4119.6C15—C14—C13118.8 (2)
C3—C4—H4119.6C19—C14—C13123.2 (2)
C4—C5—C6120.6 (3)C16—C15—C14121.4 (2)
C4—C5—H5119.7C16—C15—H15119.3
C6—C5—H5119.7C14—C15—H15119.3
C5—C6—C1120.0 (4)C15—C16—C17120.3 (3)
C5—C6—H6120.0C15—C16—H16119.9
C1—C6—H6120.0C17—C16—H16119.9
N1—C7—C8124.8 (2)N2—C17—C18121.2 (3)
N1—C7—Cl1115.67 (19)N2—C17—C16120.3 (3)
C8—C7—Cl1119.5 (2)C18—C17—C16118.5 (2)
C9—C8—C7117.7 (2)C19—C18—C17121.0 (2)
C9—C8—H8121.2C19—C18—H18119.5
C7—C8—H8121.2C17—C18—H18119.5
C8—C9—C10120.1 (2)C18—C19—C14120.8 (3)
C8—C9—H9120.0C18—C19—H19119.6
C10—C9—H9120.0C14—C19—H19119.6
C11—C10—C9116.8 (2)C7—N1—C11116.3 (2)
C11—C10—C12123.1 (2)C13—O2—C12115.83 (19)
C9—C10—C12120.1 (2)C17—N2—H1N119 (2)
N1—C11—C10124.4 (2)C17—N2—H2N119 (3)
N1—C11—H11117.8H1N—N2—H2N119 (4)
C10—C11—H11117.8
C6—C1—C2—C30.8 (6)O2—C13—C14—C193.3 (3)
C1—C2—C3—C41.1 (6)C19—C14—C15—C160.2 (4)
C2—C3—C4—C51.1 (6)C13—C14—C15—C16179.7 (2)
C3—C4—C5—C60.8 (5)C14—C15—C16—C170.6 (4)
C4—C5—C6—C10.4 (6)C15—C16—C17—N2178.5 (3)
C2—C1—C6—C50.5 (6)C15—C16—C17—C180.3 (4)
N1—C7—C8—C90.3 (4)N2—C17—C18—C19177.8 (3)
Cl1—C7—C8—C9179.59 (19)C16—C17—C18—C190.4 (4)
C7—C8—C9—C100.0 (4)C17—C18—C19—C140.8 (4)
C8—C9—C10—C110.2 (4)C15—C14—C19—C180.5 (4)
C8—C9—C10—C12178.8 (2)C13—C14—C19—C18179.0 (2)
C9—C10—C11—N10.2 (4)C8—C7—N1—C110.2 (4)
C12—C10—C11—N1178.8 (2)Cl1—C7—N1—C11179.64 (18)
C11—C10—C12—O214.5 (3)C10—C11—N1—C70.0 (4)
C9—C10—C12—O2167.0 (2)O1—C13—O2—C121.6 (4)
O1—C13—C14—C152.8 (4)C14—C13—O2—C12178.34 (19)
O2—C13—C14—C15177.2 (2)C10—C12—O2—C13176.4 (2)
O1—C13—C14—C19176.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···N1i0.80 (4)2.35 (4)3.143 (4)172 (4)
Symmetry code: (i) x+1/2, y+3/2, z+1.
 

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