The ester molecule of the title compound, C
13H
11ClN
2O
2·C
6H
6, 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
CCDC reference: 640249
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.048
- wR factor = 0.138
- Data-to-parameter ratio = 18.2
checkCIF/PLATON results
No syntax errors found
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
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·C6H6 | F(000) = 1424 |
Mr = 340.80 | Dx = 1.296 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 1755 reflections |
a = 20.688 (5) Å | θ = 1.5–28.3° |
b = 6.289 (5) Å | µ = 0.23 mm−1 |
c = 26.845 (5) Å | T = 293 K |
β = 90.799 (5)° | Block, yellow |
V = 3492 (3) Å3 | 0.37 × 0.21 × 0.16 mm |
Z = 8 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 4056 independent reflections |
Radiation source: fine-focus sealed tube | 1774 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ω scans | θmax = 28.3°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −27→24 |
Tmin = 0.29, Tmax = 0.34 | k = −8→8 |
10258 measured reflections | l = −35→20 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H 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 parameters | Δρmax = 0.15 e Å−3 |
6 restraints | Δρmin = −0.17 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.3137 (2) | 0.3905 (7) | 0.72658 (18) | 0.1229 (14) | |
H1 | 0.2833 | 0.2842 | 0.7207 | 0.148* | |
C2 | 0.3648 (3) | 0.3552 (6) | 0.75936 (16) | 0.1249 (14) | |
H2 | 0.3688 | 0.2260 | 0.7760 | 0.150* | |
C3 | 0.40959 (18) | 0.5145 (7) | 0.76695 (14) | 0.1099 (12) | |
H3 | 0.4446 | 0.4926 | 0.7884 | 0.132* | |
C4 | 0.40249 (16) | 0.7028 (6) | 0.74314 (13) | 0.0959 (10) | |
H4 | 0.4324 | 0.8108 | 0.7488 | 0.115* | |
C5 | 0.35246 (17) | 0.7359 (6) | 0.71124 (12) | 0.0956 (10) | |
H5 | 0.3486 | 0.8657 | 0.6949 | 0.115* | |
C6 | 0.30798 (17) | 0.5820 (7) | 0.70289 (15) | 0.1089 (12) | |
H6 | 0.2735 | 0.6064 | 0.6810 | 0.131* | |
C7 | 0.49449 (13) | 0.7476 (4) | 0.37435 (9) | 0.0625 (7) | |
C8 | 0.54091 (12) | 0.5946 (4) | 0.38159 (10) | 0.0665 (7) | |
H8 | 0.5805 | 0.6025 | 0.3657 | 0.080* | |
C9 | 0.52690 (12) | 0.4298 (4) | 0.41292 (10) | 0.0662 (7) | |
H9 | 0.5573 | 0.3233 | 0.4187 | 0.079* | |
C10 | 0.46751 (11) | 0.4215 (3) | 0.43607 (9) | 0.0543 (6) | |
C11 | 0.42479 (12) | 0.5845 (4) | 0.42567 (10) | 0.0653 (7) | |
H11 | 0.3847 | 0.5808 | 0.4408 | 0.078* | |
C12 | 0.45169 (11) | 0.2392 (4) | 0.46951 (10) | 0.0652 (7) | |
H12A | 0.4439 | 0.1121 | 0.4499 | 0.078* | |
H12B | 0.4876 | 0.2118 | 0.4922 | 0.078* | |
C13 | 0.37215 (12) | 0.1385 (4) | 0.52713 (10) | 0.0621 (7) | |
C14 | 0.31548 (11) | 0.2063 (4) | 0.55505 (9) | 0.0575 (6) | |
C15 | 0.28871 (12) | 0.0665 (4) | 0.58908 (10) | 0.0678 (7) | |
H15 | 0.3073 | −0.0669 | 0.5936 | 0.081* | |
C16 | 0.23542 (13) | 0.1210 (4) | 0.61612 (11) | 0.0714 (8) | |
H16 | 0.2186 | 0.0252 | 0.6389 | 0.086* | |
C17 | 0.20634 (12) | 0.3198 (4) | 0.60955 (10) | 0.0654 (7) | |
C18 | 0.23273 (12) | 0.4592 (4) | 0.57552 (10) | 0.0661 (7) | |
H18 | 0.2138 | 0.5918 | 0.5706 | 0.079* | |
C19 | 0.28644 (12) | 0.4048 (4) | 0.54892 (10) | 0.0626 (7) | |
H19 | 0.3037 | 0.5015 | 0.5265 | 0.075* | |
N1 | 0.43721 (10) | 0.7473 (3) | 0.39525 (8) | 0.0683 (6) | |
O1 | 0.39706 (9) | −0.0343 (3) | 0.52974 (8) | 0.0891 (7) | |
O2 | 0.39484 (7) | 0.2923 (3) | 0.49716 (6) | 0.0636 (5) | |
Cl1 | 0.50998 (4) | 0.96069 (12) | 0.33530 (3) | 0.0927 (3) | |
N2 | 0.15393 (13) | 0.3764 (5) | 0.63745 (11) | 0.0903 (9) | |
H1N | 0.1354 (16) | 0.276 (6) | 0.6575 (13) | 0.136* | |
H2N | 0.1336 (18) | 0.480 (6) | 0.6299 (15) | 0.136* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.132 (4) | 0.110 (3) | 0.127 (4) | −0.047 (3) | 0.011 (3) | −0.025 (3) |
C2 | 0.183 (4) | 0.082 (3) | 0.111 (3) | 0.006 (3) | 0.029 (3) | 0.018 (2) |
C3 | 0.100 (3) | 0.136 (3) | 0.093 (3) | 0.011 (3) | −0.007 (2) | 0.022 (3) |
C4 | 0.095 (2) | 0.115 (3) | 0.078 (2) | −0.026 (2) | −0.005 (2) | 0.009 (2) |
C5 | 0.107 (3) | 0.092 (2) | 0.088 (2) | 0.001 (2) | −0.009 (2) | 0.004 (2) |
C6 | 0.084 (2) | 0.128 (3) | 0.114 (3) | 0.000 (2) | −0.016 (2) | −0.010 (3) |
C7 | 0.0705 (17) | 0.0529 (15) | 0.0643 (17) | 0.0000 (13) | 0.0020 (15) | −0.0029 (13) |
C8 | 0.0587 (15) | 0.0682 (18) | 0.0729 (18) | 0.0060 (13) | 0.0080 (14) | −0.0040 (15) |
C9 | 0.0605 (16) | 0.0642 (17) | 0.0737 (19) | 0.0153 (13) | −0.0003 (15) | −0.0045 (15) |
C10 | 0.0572 (15) | 0.0454 (14) | 0.0601 (16) | 0.0065 (11) | −0.0025 (13) | −0.0073 (12) |
C11 | 0.0604 (15) | 0.0591 (16) | 0.0766 (19) | 0.0114 (13) | 0.0107 (14) | 0.0050 (14) |
C12 | 0.0648 (16) | 0.0570 (16) | 0.0740 (18) | 0.0151 (13) | 0.0066 (14) | 0.0006 (14) |
C13 | 0.0643 (16) | 0.0552 (16) | 0.0665 (18) | 0.0080 (13) | −0.0053 (14) | 0.0049 (14) |
C14 | 0.0601 (15) | 0.0523 (15) | 0.0598 (16) | 0.0071 (12) | −0.0076 (13) | 0.0036 (13) |
C15 | 0.0658 (17) | 0.0567 (16) | 0.081 (2) | 0.0102 (13) | −0.0023 (16) | 0.0102 (15) |
C16 | 0.0675 (17) | 0.0683 (18) | 0.079 (2) | 0.0022 (14) | 0.0020 (15) | 0.0155 (15) |
C17 | 0.0574 (16) | 0.0716 (18) | 0.0672 (18) | 0.0080 (13) | −0.0019 (14) | −0.0018 (15) |
C18 | 0.0686 (17) | 0.0538 (15) | 0.0760 (19) | 0.0138 (13) | 0.0004 (15) | 0.0050 (14) |
C19 | 0.0649 (16) | 0.0559 (16) | 0.0670 (17) | 0.0066 (12) | −0.0010 (14) | 0.0054 (13) |
N1 | 0.0683 (14) | 0.0589 (14) | 0.0780 (16) | 0.0109 (11) | 0.0110 (12) | 0.0092 (12) |
O1 | 0.0892 (13) | 0.0625 (12) | 0.1162 (17) | 0.0284 (10) | 0.0210 (12) | 0.0241 (11) |
O2 | 0.0661 (11) | 0.0536 (10) | 0.0712 (12) | 0.0114 (8) | 0.0072 (9) | 0.0041 (9) |
Cl1 | 0.1002 (6) | 0.0746 (5) | 0.1039 (7) | 0.0004 (4) | 0.0211 (5) | 0.0202 (4) |
N2 | 0.0773 (18) | 0.091 (2) | 0.103 (2) | 0.0173 (14) | 0.0183 (16) | 0.0109 (17) |
Geometric parameters (Å, º) top
C1—C6 | 1.366 (5) | C11—N1 | 1.337 (3) |
C1—C2 | 1.384 (5) | C11—H11 | 0.9300 |
C1—H1 | 0.9300 | C12—O2 | 1.439 (3) |
C2—C3 | 1.379 (5) | C12—H12A | 0.9700 |
C2—H2 | 0.9300 | C12—H12B | 0.9700 |
C3—C4 | 1.353 (4) | C13—O1 | 1.204 (3) |
C3—H3 | 0.9300 | C13—O2 | 1.347 (3) |
C4—C5 | 1.350 (4) | C13—C14 | 1.464 (3) |
C4—H4 | 0.9300 | C14—C15 | 1.389 (3) |
C5—C6 | 1.352 (4) | C14—C19 | 1.394 (3) |
C5—H5 | 0.9300 | C15—C16 | 1.372 (3) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—N1 | 1.318 (3) | C16—C17 | 1.398 (4) |
C7—C8 | 1.372 (3) | C16—H16 | 0.9300 |
C7—Cl1 | 1.734 (3) | C17—N2 | 1.373 (3) |
C8—C9 | 1.368 (4) | C17—C18 | 1.384 (4) |
C8—H8 | 0.9300 | C18—C19 | 1.372 (3) |
C9—C10 | 1.386 (3) | C18—H18 | 0.9300 |
C9—H9 | 0.9300 | C19—H19 | 0.9300 |
C10—C11 | 1.379 (3) | N2—H1N | 0.92 (4) |
C10—C12 | 1.495 (3) | N2—H2N | 0.80 (4) |
| | | |
C6—C1—C2 | 119.9 (4) | O2—C12—C10 | 108.62 (19) |
C6—C1—H1 | 120.1 | O2—C12—H12A | 110.0 |
C2—C1—H1 | 120.1 | C10—C12—H12A | 110.0 |
C3—C2—C1 | 118.9 (4) | O2—C12—H12B | 110.0 |
C3—C2—H2 | 120.6 | C10—C12—H12B | 110.0 |
C1—C2—H2 | 120.6 | H12A—C12—H12B | 108.3 |
C4—C3—C2 | 119.9 (4) | O1—C13—O2 | 122.0 (2) |
C4—C3—H3 | 120.1 | O1—C13—C14 | 125.3 (2) |
C2—C3—H3 | 120.1 | O2—C13—C14 | 112.6 (2) |
C5—C4—C3 | 120.8 (3) | C15—C14—C19 | 118.0 (2) |
C5—C4—H4 | 119.6 | C15—C14—C13 | 118.8 (2) |
C3—C4—H4 | 119.6 | C19—C14—C13 | 123.2 (2) |
C4—C5—C6 | 120.6 (3) | C16—C15—C14 | 121.4 (2) |
C4—C5—H5 | 119.7 | C16—C15—H15 | 119.3 |
C6—C5—H5 | 119.7 | C14—C15—H15 | 119.3 |
C5—C6—C1 | 120.0 (4) | C15—C16—C17 | 120.3 (3) |
C5—C6—H6 | 120.0 | C15—C16—H16 | 119.9 |
C1—C6—H6 | 120.0 | C17—C16—H16 | 119.9 |
N1—C7—C8 | 124.8 (2) | N2—C17—C18 | 121.2 (3) |
N1—C7—Cl1 | 115.67 (19) | N2—C17—C16 | 120.3 (3) |
C8—C7—Cl1 | 119.5 (2) | C18—C17—C16 | 118.5 (2) |
C9—C8—C7 | 117.7 (2) | C19—C18—C17 | 121.0 (2) |
C9—C8—H8 | 121.2 | C19—C18—H18 | 119.5 |
C7—C8—H8 | 121.2 | C17—C18—H18 | 119.5 |
C8—C9—C10 | 120.1 (2) | C18—C19—C14 | 120.8 (3) |
C8—C9—H9 | 120.0 | C18—C19—H19 | 119.6 |
C10—C9—H9 | 120.0 | C14—C19—H19 | 119.6 |
C11—C10—C9 | 116.8 (2) | C7—N1—C11 | 116.3 (2) |
C11—C10—C12 | 123.1 (2) | C13—O2—C12 | 115.83 (19) |
C9—C10—C12 | 120.1 (2) | C17—N2—H1N | 119 (2) |
N1—C11—C10 | 124.4 (2) | C17—N2—H2N | 119 (3) |
N1—C11—H11 | 117.8 | H1N—N2—H2N | 119 (4) |
C10—C11—H11 | 117.8 | | |
| | | |
C6—C1—C2—C3 | −0.8 (6) | O2—C13—C14—C19 | 3.3 (3) |
C1—C2—C3—C4 | 1.1 (6) | C19—C14—C15—C16 | −0.2 (4) |
C2—C3—C4—C5 | −1.1 (6) | C13—C14—C15—C16 | −179.7 (2) |
C3—C4—C5—C6 | 0.8 (5) | C14—C15—C16—C17 | 0.6 (4) |
C4—C5—C6—C1 | −0.4 (6) | C15—C16—C17—N2 | −178.5 (3) |
C2—C1—C6—C5 | 0.5 (6) | C15—C16—C17—C18 | −0.3 (4) |
N1—C7—C8—C9 | −0.3 (4) | N2—C17—C18—C19 | 177.8 (3) |
Cl1—C7—C8—C9 | 179.59 (19) | C16—C17—C18—C19 | −0.4 (4) |
C7—C8—C9—C10 | 0.0 (4) | C17—C18—C19—C14 | 0.8 (4) |
C8—C9—C10—C11 | 0.2 (4) | C15—C14—C19—C18 | −0.5 (4) |
C8—C9—C10—C12 | 178.8 (2) | C13—C14—C19—C18 | 179.0 (2) |
C9—C10—C11—N1 | −0.2 (4) | C8—C7—N1—C11 | 0.2 (4) |
C12—C10—C11—N1 | −178.8 (2) | Cl1—C7—N1—C11 | −179.64 (18) |
C11—C10—C12—O2 | −14.5 (3) | C10—C11—N1—C7 | 0.0 (4) |
C9—C10—C12—O2 | 167.0 (2) | O1—C13—O2—C12 | −1.6 (4) |
O1—C13—C14—C15 | 2.8 (4) | C14—C13—O2—C12 | 178.34 (19) |
O2—C13—C14—C15 | −177.2 (2) | C10—C12—O2—C13 | 176.4 (2) |
O1—C13—C14—C19 | −176.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N1i | 0.80 (4) | 2.35 (4) | 3.143 (4) | 172 (4) |
Symmetry code: (i) −x+1/2, −y+3/2, −z+1. |