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Structures are reported here for eight further substituted N-aryl-2-chloronicotinamides, 2-ClC5H3NCONHC6H4X-4′. When X = H, compound (I) (C12H9ClN2O), the molecules are linked into sheets by N—H...N, C—H...π(pyridyl) and C—H...π(arene) hydrogen bonds. For X = CH3, compound (II) (C13H11ClN2O, triclinic P\bar 1 with Z′ = 2), the molecules are linked into sheets by N—H...O, C—H...O and C—H...π(arene) hydrogen bonds. Compound (III), where X = F, crystallizes as a monohydrate (C12H8ClFN2O·H2O) and sheets are formed by N—H...O, O—H...O and O—H...N hydrogen bonds and aromatic π...π stacking interactions. Crystals of compound (IV), where X = Cl (C12H8Cl2N2O, monoclinic P21 with Z′ = 4) exhibit inversion twinning: the molecules are linked by N—H...O hydrogen bonds into four independent chains, linked in pairs by C—H...π(arene) hydrogen bonds. When X = Br, compound (V) (C12H8BrClN2O), the molecules are linked into sheets by N—H...O and C—H...N hydrogen bonds, while in compound (VI), where X = I (C12H8ClIN2O), the molecules are linked into a three-dimensional framework by N—H...O and C—H...π(arene) hydrogen bonds and an iodo...N(pyridyl) interaction. For X = CH3O, compound (VII) (C13H11ClN2O2), the molecules are linked into chains by a single N—H...O hydrogen bond. Compound (VIII) (C13H8ClN3O, triclinic P\bar 1 with Z′ = 2), where X = CN, forms a complex three-dimensional framework by N—H...N, C—H...N and C—H...O hydrogen bonds and two independent aromatic π...π stacking interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106015497/bm5033sup1.cif
Contains datablocks global, I, II, III, IV, V, VI, VII, VIII

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106015497/bm5033Isup2.fcf
Contains datablock I

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106015497/bm5033IIsup3.fcf
Contains datablock 527

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106015497/bm5033IIIsup4.fcf
Contains datablock 569

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106015497/bm5033IVsup5.fcf
Contains datablock 743m

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106015497/bm5033Vsup6.fcf
Contains datablock V

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106015497/bm5033VIsup7.fcf
Contains datablock 744

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106015497/bm5033VIIsup8.fcf
Contains datablock 594

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106015497/bm5033VIIIsup9.fcf
Contains datablock 745

CCDC references: 618463; 618464; 618465; 618466; 618467; 618468; 618469; 618470

Comment top

In full text version

Experimental top

In full text version

Refinement top

In full text version

Computing details top

Data collection: COLLECT (Hooft, 1999) for (I), (III), (IV), (V), (VI), (VII), (VIII); Bruker APEX2 (Bruker, 2004) for (II). Cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT for (I), (III), (IV), (V), (VI), (VII), (VIII); SAINT (Bruker, 2004) for (II). Data reduction: DENZO & COLLECT for (I), (III), (IV), (V), (VI), (VII), (VIII); SAINT for (II). For all compounds, program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

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In full text version
(I) N-phenyl-2-chloronicotinamide top
Crystal data top
C12H9ClN2OF(000) = 960
Mr = 232.66Dx = 1.442 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 2446 reflections
a = 13.2296 (6) Åθ = 3.1–27.5°
b = 21.0744 (10) ŵ = 0.33 mm1
c = 7.6898 (16) ÅT = 120 K
V = 2144.0 (5) Å3Needle, colourless
Z = 80.24 × 0.09 × 0.02 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2446 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1724 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.104
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ & ω scansh = 1617
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 2727
Tmin = 0.943, Tmax = 0.993l = 99
17837 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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0479P)2 + 1.6007P]
where P = (Fo2 + 2Fc2)/3
2446 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C12H9ClN2OV = 2144.0 (5) Å3
Mr = 232.66Z = 8
Orthorhombic, PccnMo Kα radiation
a = 13.2296 (6) ŵ = 0.33 mm1
b = 21.0744 (10) ÅT = 120 K
c = 7.6898 (16) Å0.24 × 0.09 × 0.02 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2446 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
1724 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.993Rint = 0.104
17837 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.07Δρmax = 0.28 e Å3
2446 reflectionsΔρmin = 0.28 e Å3
145 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.25408 (16)0.57579 (10)0.9067 (3)0.0262 (5)
C120.32767 (18)0.60070 (12)0.8111 (4)0.0238 (6)
Cl10.31180 (5)0.68016 (3)0.75558 (10)0.0305 (2)
C130.41523 (18)0.56871 (12)0.7615 (3)0.0220 (5)
C140.42677 (19)0.50752 (12)0.8256 (3)0.0248 (6)
C150.3523 (2)0.48067 (13)0.9271 (3)0.0282 (6)
C160.2668 (2)0.51593 (13)0.9605 (4)0.0288 (6)
C170.49778 (19)0.59498 (12)0.6469 (4)0.0246 (6)
O10.58540 (13)0.59291 (10)0.6968 (3)0.0390 (5)
N210.46640 (16)0.61551 (10)0.4897 (3)0.0249 (5)
C210.52498 (19)0.64341 (12)0.3554 (3)0.0235 (6)
C220.4731 (2)0.66828 (13)0.2137 (4)0.0296 (7)
C230.5248 (2)0.69702 (13)0.0789 (4)0.0331 (7)
C240.6292 (2)0.70101 (13)0.0842 (4)0.0295 (6)
C250.6809 (2)0.67565 (13)0.2231 (4)0.0293 (6)
C260.63023 (19)0.64704 (12)0.3598 (4)0.0252 (6)
H140.48620.48410.79950.030*
H150.35970.43900.97270.034*
H160.21390.49671.02520.035*
H210.40120.61250.46880.030*
H220.40150.66550.20960.035*
H230.48870.71400.01730.040*
H240.66500.72120.00760.035*
H250.75260.67780.22530.035*
H260.66670.63010.45550.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0225 (11)0.0302 (12)0.0261 (13)0.0000 (10)0.0039 (10)0.0002 (10)
C120.0234 (13)0.0253 (13)0.0227 (14)0.0002 (10)0.0028 (11)0.0013 (11)
Cl10.0259 (3)0.0258 (3)0.0400 (4)0.0033 (3)0.0028 (3)0.0040 (3)
C130.0183 (12)0.0277 (13)0.0202 (14)0.0002 (10)0.0021 (11)0.0010 (11)
C140.0241 (13)0.0294 (14)0.0210 (14)0.0029 (12)0.0052 (12)0.0030 (11)
C150.0333 (15)0.0256 (14)0.0257 (15)0.0025 (12)0.0002 (13)0.0023 (11)
C160.0299 (15)0.0317 (14)0.0247 (15)0.0057 (12)0.0040 (12)0.0001 (12)
C170.0205 (12)0.0282 (14)0.0250 (15)0.0045 (11)0.0003 (11)0.0008 (11)
O10.0193 (10)0.0645 (14)0.0333 (12)0.0000 (10)0.0020 (9)0.0148 (10)
N210.0162 (10)0.0334 (13)0.0250 (13)0.0001 (9)0.0004 (10)0.0055 (10)
C210.0225 (13)0.0269 (14)0.0213 (15)0.0016 (11)0.0008 (12)0.0021 (11)
C220.0198 (13)0.0369 (16)0.0319 (17)0.0011 (11)0.0009 (12)0.0045 (12)
C230.0312 (16)0.0367 (16)0.0315 (17)0.0011 (13)0.0018 (13)0.0092 (13)
C240.0300 (15)0.0328 (15)0.0257 (15)0.0044 (12)0.0061 (13)0.0018 (12)
C250.0237 (14)0.0344 (15)0.0297 (16)0.0042 (12)0.0036 (12)0.0046 (12)
C260.0224 (13)0.0280 (14)0.0251 (15)0.0006 (11)0.0002 (12)0.0027 (11)
Geometric parameters (Å, º) top
N11—C121.328 (3)N21—C211.419 (3)
N11—C161.338 (3)N21—H210.8796
C12—C131.394 (3)C21—C221.390 (4)
C12—Cl11.741 (3)C21—C261.395 (3)
C13—C141.389 (3)C22—C231.382 (4)
C13—C171.509 (4)C22—H220.95
C14—C151.378 (4)C23—C241.385 (4)
C14—H140.95C23—H230.95
C15—C161.378 (4)C24—C251.376 (4)
C15—H150.95C24—H240.95
C16—H160.95C25—C261.385 (4)
C17—O11.222 (3)C25—H250.95
C17—N211.349 (3)C26—H260.95
C12—N11—C16116.9 (2)C17—N21—H21116.3
N11—C12—C13124.7 (2)C21—N21—H21115.6
N11—C12—Cl1115.32 (19)C22—C21—C26119.4 (2)
C13—C12—Cl1119.9 (2)C22—C21—N21117.2 (2)
C14—C13—C12116.3 (2)C26—C21—N21123.4 (2)
C14—C13—C17117.9 (2)C23—C22—C21120.6 (2)
C12—C13—C17125.8 (2)C23—C22—H22119.7
C15—C14—C13120.2 (2)C21—C22—H22119.7
C15—C14—H14119.9C22—C23—C24119.8 (3)
C13—C14—H14119.9C22—C23—H23120.1
C16—C15—C14118.1 (2)C24—C23—H23120.1
C16—C15—H15120.9C25—C24—C23119.7 (3)
C14—C15—H15120.9C25—C24—H24120.2
N11—C16—C15123.6 (3)C23—C24—H24120.2
N11—C16—H16118.2C24—C25—C26121.2 (2)
C15—C16—H16118.2C24—C25—H25119.4
O1—C17—N21125.8 (2)C26—C25—H25119.4
O1—C17—C13119.4 (2)C25—C26—C21119.3 (3)
N21—C17—C13114.7 (2)C25—C26—H26120.4
C17—N21—C21128.1 (2)C21—C26—H26120.4
C16—N11—C12—C131.1 (4)C12—C13—C17—N2156.2 (4)
C16—N11—C12—Cl1176.12 (19)O1—C17—N21—C215.5 (4)
N11—C12—C13—C143.4 (4)C13—C17—N21—C21178.8 (2)
Cl1—C12—C13—C14173.71 (19)C17—N21—C21—C22171.8 (2)
N11—C12—C13—C17177.3 (2)C17—N21—C21—C268.0 (4)
Cl1—C12—C13—C175.7 (4)C26—C21—C22—C230.7 (4)
C12—C13—C14—C152.3 (4)N21—C21—C22—C23179.1 (2)
C17—C13—C14—C15178.3 (2)C21—C22—C23—C240.2 (4)
C13—C14—C15—C160.7 (4)C22—C23—C24—C250.7 (4)
C12—N11—C16—C152.4 (4)C23—C24—C25—C261.1 (4)
C14—C15—C16—N113.2 (4)C24—C25—C26—C210.6 (4)
C14—C13—C17—O151.6 (4)C22—C21—C26—C250.3 (4)
C12—C13—C17—O1127.8 (3)N21—C21—C26—C25179.5 (2)
C14—C13—C17—N21124.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N11i0.882.253.101 (3)164
C15—H15···Cg1ii0.952.893.535 (3)126
C16—H16···Cg2iii0.952.873.464 (3)121
Symmetry codes: (i) x+1/2, y, z1/2; (ii) x+1, y+1, z+1; (iii) x+1/2, y, z+1/2.
(II) N-(4-Methylphenyl)-2-chloronicotinamide top
Crystal data top
C13H11ClN2OZ = 4
Mr = 246.69F(000) = 512
Triclinic, P1Dx = 1.390 Mg m3
Hall symbol: -P 1Synchrotron radiation, λ = 0.67510 Å
a = 9.6824 (6) ÅCell parameters from 6881 reflections
b = 11.3082 (7) Åθ = 2.1–28.8°
c = 11.5139 (7) ŵ = 0.31 mm1
α = 77.453 (2)°T = 120 K
β = 73.445 (2)°Needle, colourless
γ = 87.978 (2)°0.10 × 0.02 × 0.02 mm
V = 1179.07 (13) Å3
Data collection top
Bruker SMART APEX2 CCD
diffractometer
6881 independent reflections
Radiation source: Daresbury SRS station 9.8, (Cernik et al., 1997)5217 reflections with ( > 2σ(I)
Silicon 111 monochromatorRint = 0.022
fine–slice ω scansθmax = 28.8°, θmin = 2.1°
Absorption correction: multi-scan
Bruker SADABS (Bruker, 2004)
h = 1313
Tmin = 0.970, Tmax = 0.994k = 1616
12982 measured reflectionsl = 1616
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0648P)2 + 0.3225P]
where P = (Fo2 + 2Fc2)/3
6881 reflections(Δ/σ)max = 0.001
309 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C13H11ClN2Oγ = 87.978 (2)°
Mr = 246.69V = 1179.07 (13) Å3
Triclinic, P1Z = 4
a = 9.6824 (6) ÅSynchrotron radiation, λ = 0.67510 Å
b = 11.3082 (7) ŵ = 0.31 mm1
c = 11.5139 (7) ÅT = 120 K
α = 77.453 (2)°0.10 × 0.02 × 0.02 mm
β = 73.445 (2)°
Data collection top
Bruker SMART APEX2 CCD
diffractometer
6881 independent reflections
Absorption correction: multi-scan
Bruker SADABS (Bruker, 2004)
5217 reflections with ( > 2σ(I)
Tmin = 0.970, Tmax = 0.994Rint = 0.022
12982 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.02Δρmax = 0.43 e Å3
6881 reflectionsΔρmin = 0.30 e Å3
309 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.86915 (14)0.73134 (12)0.08967 (11)0.0221 (3)
C120.84419 (15)0.70831 (13)0.03187 (12)0.0183 (3)
Cl10.83100 (5)0.55573 (3)0.10547 (3)0.02910 (11)
C130.83069 (14)0.79583 (13)0.10341 (12)0.0168 (3)
C140.83825 (17)0.91586 (14)0.04073 (13)0.0220 (3)
C150.86423 (18)0.94293 (14)0.08708 (13)0.0245 (3)
C160.88058 (17)0.84842 (14)0.14807 (13)0.0236 (3)
C170.82579 (15)0.76179 (13)0.23844 (12)0.0173 (3)
O10.93912 (11)0.74347 (11)0.26770 (9)0.0255 (2)
N210.69517 (13)0.75458 (11)0.31986 (10)0.0182 (2)
C210.66503 (14)0.71569 (13)0.45110 (12)0.0168 (3)
C220.54054 (15)0.64547 (14)0.51422 (13)0.0201 (3)
C230.50576 (16)0.60308 (14)0.64181 (13)0.0223 (3)
C240.59492 (16)0.62974 (14)0.70977 (12)0.0209 (3)
C250.71711 (16)0.70342 (14)0.64523 (13)0.0214 (3)
C260.75349 (15)0.74657 (14)0.51730 (13)0.0196 (3)
C2410.56166 (18)0.57879 (16)0.84700 (13)0.0274 (3)
N310.09859 (14)0.76364 (12)0.58897 (11)0.0225 (3)
C320.17080 (16)0.79085 (13)0.47011 (13)0.0192 (3)
Cl30.20022 (5)0.94486 (3)0.40386 (4)0.03240 (11)
C330.22193 (15)0.70691 (13)0.39653 (12)0.0175 (3)
C340.19083 (15)0.58576 (13)0.45303 (13)0.0200 (3)
C350.11540 (16)0.55384 (14)0.57837 (13)0.0215 (3)
C360.07258 (16)0.64550 (14)0.64210 (13)0.0219 (3)
C370.31481 (15)0.74411 (14)0.26399 (12)0.0194 (3)
O30.44343 (12)0.76878 (14)0.24022 (10)0.0373 (3)
N410.24535 (12)0.74497 (11)0.17848 (10)0.0171 (2)
C410.30028 (14)0.78264 (13)0.04773 (12)0.0164 (3)
C420.21841 (15)0.75010 (13)0.02321 (12)0.0192 (3)
C430.25670 (16)0.79412 (14)0.15074 (13)0.0211 (3)
C440.37751 (16)0.87086 (14)0.21107 (12)0.0205 (3)
C4410.41532 (19)0.92274 (16)0.34831 (13)0.0274 (3)
C450.46144 (16)0.89806 (14)0.13930 (13)0.0222 (3)
C460.42436 (15)0.85517 (14)0.01134 (12)0.0204 (3)
H140.82570.97910.08500.026*
H150.87071.02470.13180.029*
H160.90100.86740.23590.028*
H210.62270.75430.28790.022*
H220.47870.62630.46960.024*
H230.42010.55530.68360.027*
H250.77740.72480.69010.026*
H260.83750.79640.47560.024*
H24A0.53360.49280.86500.041*
H24B0.48240.62300.89130.041*
H24C0.64730.58730.87410.041*
H340.22080.52490.40650.024*
H350.09390.47130.61900.026*
H360.02220.62380.72790.026*
H410.15220.72810.20780.021*
H420.13620.69760.01600.023*
H430.19970.77170.19780.025*
H44A0.32800.92640.37580.041*
H44B0.48510.87110.39230.041*
H44C0.45751.00450.36630.041*
H450.54640.94730.17900.027*
H460.48320.87520.03540.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0278 (7)0.0255 (6)0.0147 (5)0.0004 (5)0.0070 (5)0.0064 (5)
C120.0191 (6)0.0206 (7)0.0149 (6)0.0015 (5)0.0044 (5)0.0036 (5)
Cl10.0429 (2)0.02044 (19)0.02131 (18)0.00353 (15)0.00605 (15)0.00230 (14)
C130.0156 (6)0.0228 (7)0.0118 (6)0.0001 (5)0.0032 (5)0.0044 (5)
C140.0279 (7)0.0226 (7)0.0160 (6)0.0040 (6)0.0058 (5)0.0067 (5)
C150.0337 (8)0.0229 (7)0.0154 (6)0.0049 (6)0.0068 (6)0.0021 (5)
C160.0298 (8)0.0280 (8)0.0131 (6)0.0044 (6)0.0067 (5)0.0043 (5)
C170.0175 (6)0.0214 (7)0.0132 (6)0.0003 (5)0.0043 (5)0.0043 (5)
O10.0162 (5)0.0439 (7)0.0158 (5)0.0009 (4)0.0056 (4)0.0039 (4)
N210.0159 (5)0.0283 (6)0.0115 (5)0.0006 (4)0.0051 (4)0.0050 (4)
C210.0171 (6)0.0238 (7)0.0103 (5)0.0021 (5)0.0033 (5)0.0066 (5)
C220.0180 (6)0.0285 (7)0.0147 (6)0.0018 (5)0.0052 (5)0.0054 (5)
C230.0203 (7)0.0289 (8)0.0152 (6)0.0019 (6)0.0019 (5)0.0032 (5)
C240.0238 (7)0.0260 (7)0.0124 (6)0.0050 (5)0.0039 (5)0.0056 (5)
C250.0220 (7)0.0302 (8)0.0153 (6)0.0020 (6)0.0071 (5)0.0095 (5)
C260.0181 (6)0.0270 (7)0.0157 (6)0.0011 (5)0.0052 (5)0.0075 (5)
C2410.0318 (8)0.0363 (9)0.0125 (6)0.0040 (7)0.0049 (6)0.0042 (6)
N310.0278 (7)0.0256 (6)0.0133 (5)0.0024 (5)0.0043 (5)0.0048 (5)
C320.0227 (7)0.0205 (7)0.0141 (6)0.0004 (5)0.0063 (5)0.0016 (5)
Cl30.0471 (3)0.0213 (2)0.02420 (19)0.00033 (16)0.00680 (17)0.00040 (14)
C330.0159 (6)0.0259 (7)0.0115 (5)0.0000 (5)0.0056 (5)0.0029 (5)
C340.0197 (7)0.0243 (7)0.0172 (6)0.0008 (5)0.0054 (5)0.0071 (5)
C350.0220 (7)0.0228 (7)0.0177 (6)0.0005 (5)0.0055 (5)0.0001 (5)
C360.0228 (7)0.0281 (8)0.0133 (6)0.0004 (6)0.0045 (5)0.0024 (5)
C370.0170 (6)0.0294 (7)0.0116 (6)0.0009 (5)0.0048 (5)0.0029 (5)
O30.0172 (5)0.0745 (10)0.0175 (5)0.0082 (5)0.0072 (4)0.0001 (6)
N410.0150 (5)0.0259 (6)0.0103 (5)0.0014 (4)0.0032 (4)0.0039 (4)
C410.0167 (6)0.0229 (7)0.0101 (5)0.0019 (5)0.0038 (5)0.0049 (5)
C420.0178 (6)0.0260 (7)0.0147 (6)0.0001 (5)0.0046 (5)0.0060 (5)
C430.0226 (7)0.0303 (8)0.0137 (6)0.0034 (6)0.0076 (5)0.0089 (5)
C440.0242 (7)0.0251 (7)0.0116 (6)0.0037 (5)0.0040 (5)0.0045 (5)
C4410.0341 (9)0.0335 (9)0.0121 (6)0.0041 (7)0.0046 (6)0.0031 (6)
C450.0226 (7)0.0287 (8)0.0132 (6)0.0036 (6)0.0024 (5)0.0027 (5)
C460.0197 (7)0.0281 (7)0.0139 (6)0.0034 (5)0.0048 (5)0.0051 (5)
Geometric parameters (Å, º) top
N11—C121.3182 (17)N31—C321.3203 (17)
N11—C161.341 (2)N31—C361.3428 (19)
C12—C131.3996 (19)C32—C331.393 (2)
C12—Cl11.7407 (15)C32—Cl31.7407 (15)
C13—C141.386 (2)C33—C341.386 (2)
C13—C171.5056 (18)C33—C371.5101 (18)
C14—C151.3861 (19)C34—C351.3921 (19)
C14—H140.95C34—H340.95
C15—C161.382 (2)C35—C361.383 (2)
C15—H150.95C35—H350.95
C16—H160.95C36—H360.95
C17—O11.2348 (16)C37—O31.2251 (18)
C17—N211.3355 (17)C37—N411.3395 (17)
N21—C211.4251 (16)N41—C411.4184 (16)
N21—H210.8803N41—H410.8803
C21—C221.3890 (19)C41—C461.3928 (19)
C21—C261.3948 (18)C41—C421.3969 (18)
C22—C231.3874 (19)C42—C431.3880 (19)
C22—H220.95C42—H420.95
C23—C241.398 (2)C43—C441.397 (2)
C23—H230.95C43—H430.95
C24—C251.395 (2)C44—C451.396 (2)
C24—C2411.5032 (19)C44—C4411.5026 (19)
C25—C261.3914 (19)C441—H44A0.98
C25—H250.95C441—H44B0.98
C26—H260.95C441—H44C0.98
C241—H24A0.98C45—C461.3911 (19)
C241—H24B0.98C45—H450.95
C241—H24C0.98C46—H460.95
C12—N11—C16116.68 (13)C32—N31—C36116.89 (13)
N11—C12—C13125.25 (13)N31—C32—C33125.15 (13)
N11—C12—Cl1115.85 (11)N31—C32—Cl3115.60 (11)
C13—C12—Cl1118.90 (10)C33—C32—Cl3119.24 (11)
C14—C13—C12116.57 (12)C34—C33—C32116.74 (12)
C14—C13—C17121.50 (12)C34—C33—C37120.95 (13)
C12—C13—C17121.55 (12)C32—C33—C37122.20 (13)
C13—C14—C15119.45 (13)C33—C34—C35119.58 (13)
C13—C14—H14120.3C33—C34—H34120.2
C15—C14—H14120.3C35—C34—H34120.2
C16—C15—C14118.57 (14)C36—C35—C34118.23 (14)
C16—C15—H15120.7C36—C35—H35120.9
C14—C15—H15120.7C34—C35—H35120.9
N11—C16—C15123.40 (13)N31—C36—C35123.37 (13)
N11—C16—H16118.3N31—C36—H36118.3
C15—C16—H16118.3C35—C36—H36118.3
O1—C17—N21124.14 (12)O3—C37—N41124.47 (13)
O1—C17—C13119.67 (12)O3—C37—C33121.01 (12)
N21—C17—C13116.18 (12)N41—C37—C33114.51 (12)
C17—N21—C21125.42 (12)C37—N41—C41127.77 (12)
C17—N21—H21114.9C37—N41—H41115.4
C21—N21—H21117.4C41—N41—H41116.4
C22—C21—C26119.55 (12)C46—C41—C42119.37 (12)
C22—C21—N21117.58 (12)C46—C41—N41123.70 (12)
C26—C21—N21122.86 (12)C42—C41—N41116.80 (12)
C23—C22—C21120.59 (13)C43—C42—C41120.29 (13)
C23—C22—H22119.7C43—C42—H42119.9
C21—C22—H22119.7C41—C42—H42119.9
C22—C23—C24120.94 (14)C42—C43—C44121.15 (13)
C22—C23—H23119.5C42—C43—H43119.4
C24—C23—H23119.5C44—C43—H43119.4
C25—C24—C23117.58 (13)C45—C44—C43117.66 (12)
C25—C24—C241121.29 (14)C45—C44—C441121.21 (14)
C23—C24—C241121.12 (14)C43—C44—C441121.13 (13)
C26—C25—C24122.13 (13)C44—C441—H44A109.5
C26—C25—H25118.9C44—C441—H44B109.5
C24—C25—H25118.9H44A—C441—H44B109.5
C25—C26—C21119.15 (13)C44—C441—H44C109.5
C25—C26—H26120.4H44A—C441—H44C109.5
C21—C26—H26120.4H44B—C441—H44C109.5
C24—C241—H24A109.5C46—C45—C44121.91 (13)
C24—C241—H24B109.5C46—C45—H45119.0
H24A—C241—H24B109.5C44—C45—H45119.0
C24—C241—H24C109.5C45—C46—C41119.50 (13)
H24A—C241—H24C109.5C45—C46—H46120.2
H24B—C241—H24C109.5C41—C46—H46120.2
C16—N11—C12—C130.8 (2)C36—N31—C32—C330.2 (2)
C16—N11—C12—Cl1179.58 (11)C36—N31—C32—Cl3179.10 (11)
N11—C12—C13—C142.9 (2)N31—C32—C33—C341.6 (2)
Cl1—C12—C13—C14178.36 (11)Cl3—C32—C33—C34177.70 (10)
N11—C12—C13—C17170.10 (13)N31—C32—C33—C37174.61 (13)
Cl1—C12—C13—C178.60 (18)Cl3—C32—C33—C376.09 (19)
C12—C13—C14—C152.7 (2)C32—C33—C34—C351.8 (2)
C17—C13—C14—C15170.38 (14)C37—C33—C34—C35174.50 (13)
C13—C14—C15—C160.6 (2)C33—C34—C35—C360.7 (2)
C12—N11—C16—C151.6 (2)C32—N31—C36—C351.0 (2)
C14—C15—C16—N111.7 (2)C34—C35—C36—N310.8 (2)
C14—C13—C17—O191.64 (18)C34—C33—C37—O397.98 (19)
C12—C13—C17—O181.05 (18)C32—C33—C37—O378.1 (2)
C14—C13—C17—N2187.78 (17)C34—C33—C37—N4180.81 (17)
C12—C13—C17—N2199.53 (16)C32—C33—C37—N41103.14 (16)
O1—C17—N21—C215.3 (2)O3—C37—N41—C415.5 (3)
C13—C17—N21—C21175.30 (13)C33—C37—N41—C41175.77 (13)
C17—N21—C21—C22141.82 (15)C37—N41—C41—C4618.0 (2)
C17—N21—C21—C2639.1 (2)C37—N41—C41—C42166.05 (14)
C26—C21—C22—C231.8 (2)C46—C41—C42—C432.9 (2)
N21—C21—C22—C23179.06 (13)N41—C41—C42—C43173.22 (13)
C21—C22—C23—C240.1 (2)C41—C42—C43—C440.4 (2)
C22—C23—C24—C252.0 (2)C42—C43—C44—C452.4 (2)
C22—C23—C24—C241176.85 (14)C42—C43—C44—C441177.36 (14)
C23—C24—C25—C262.1 (2)C43—C44—C45—C462.6 (2)
C241—C24—C25—C26176.79 (14)C441—C44—C45—C46177.08 (14)
C24—C25—C26—C210.2 (2)C44—C45—C46—C410.2 (2)
C22—C21—C26—C251.8 (2)C42—C41—C46—C452.6 (2)
N21—C21—C26—C25179.17 (13)N41—C41—C46—C45173.22 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O30.881.962.827 (2)170
N41—H41···O1i0.881.992.847 (2)163
C35—H35···O1ii0.952.483.424 (2)174
C14—H14···Cg3iii0.952.693.398 (2)132
C34—H34···Cg2ii0.952.633.398 (2)138
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1; (iii) x+1, y+2, z.
(III) N-(4-Fluorophenyl)-2-chloronicotinamide monohydrate top
Crystal data top
C12H8ClFN2O·H2OZ = 2
Mr = 268.67F(000) = 276
Triclinic, P1Dx = 1.504 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8033 (4) ÅCell parameters from 2720 reflections
b = 8.1303 (3) Åθ = 3.3–27.8°
c = 11.5356 (6) ŵ = 0.33 mm1
α = 84.032 (3)°T = 120 K
β = 84.297 (2)°Plate, colourless
γ = 69.569 (3)°0.18 × 0.16 × 0.03 mm
V = 593.32 (5) Å3
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2720 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1943 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 9.091 pixels mm-1θmax = 27.8°, θmin = 3.3°
ϕ & ω scansh = 88
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick,. 2003)
k = 910
Tmin = 0.933, Tmax = 0.990l = 1414
12303 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0536P)2 + 0.1705P]
where P = (Fo2 + 2Fc2)/3
2720 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C12H8ClFN2O·H2Oγ = 69.569 (3)°
Mr = 268.67V = 593.32 (5) Å3
Triclinic, P1Z = 2
a = 6.8033 (4) ÅMo Kα radiation
b = 8.1303 (3) ŵ = 0.33 mm1
c = 11.5356 (6) ÅT = 120 K
α = 84.032 (3)°0.18 × 0.16 × 0.03 mm
β = 84.297 (2)°
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2720 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick,. 2003)
1943 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.990Rint = 0.052
12303 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.05Δρmax = 0.26 e Å3
2720 reflectionsΔρmin = 0.29 e Å3
163 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.7571 (3)0.9978 (2)0.48546 (15)0.0235 (4)
C120.7752 (3)0.9063 (3)0.58821 (17)0.0199 (4)
Cl10.78295 (8)1.02152 (7)0.70544 (5)0.02776 (17)
C130.7785 (3)0.7329 (2)0.60679 (17)0.0197 (4)
C140.7568 (3)0.6539 (3)0.50950 (18)0.0234 (5)
C150.7400 (3)0.7458 (3)0.40094 (18)0.0258 (5)
C160.7432 (3)0.9155 (3)0.39284 (19)0.0258 (5)
C170.8196 (3)0.6272 (3)0.72202 (17)0.0209 (4)
O10.9775 (2)0.61153 (18)0.77274 (12)0.0271 (4)
N210.6788 (3)0.5477 (2)0.75786 (14)0.0209 (4)
C210.6875 (3)0.4219 (2)0.85440 (17)0.0205 (4)
C220.5108 (3)0.3715 (3)0.87844 (18)0.0231 (5)
C230.5070 (4)0.2461 (3)0.96891 (18)0.0270 (5)
C240.6789 (4)0.1759 (3)1.03364 (18)0.0277 (5)
F240.6761 (2)0.05172 (17)1.12278 (11)0.0396 (4)
C250.8533 (4)0.2245 (3)1.01359 (19)0.0288 (5)
C260.8583 (3)0.3489 (3)0.92234 (19)0.0268 (5)
O20.3127 (2)0.65660 (18)0.63096 (13)0.0276 (4)
H140.75340.53740.51770.028*
H150.72670.69350.33360.031*
H160.73530.97750.31800.031*
H210.56060.58390.71590.025*
H220.39270.42320.83270.028*
H230.38800.20980.98550.032*
H250.96890.17401.06120.035*
H260.97840.38390.90660.032*
H2A0.27980.75990.57920.041*
H2B0.20580.64580.66890.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0174 (9)0.0273 (9)0.0255 (10)0.0077 (7)0.0038 (7)0.0021 (7)
C120.0127 (10)0.0235 (10)0.0238 (11)0.0060 (8)0.0026 (8)0.0026 (8)
Cl10.0311 (3)0.0269 (3)0.0277 (3)0.0113 (2)0.0042 (2)0.0056 (2)
C130.0122 (10)0.0223 (10)0.0235 (11)0.0052 (8)0.0003 (8)0.0001 (8)
C140.0182 (11)0.0239 (11)0.0277 (12)0.0062 (8)0.0033 (9)0.0027 (9)
C150.0214 (11)0.0311 (12)0.0245 (12)0.0075 (9)0.0033 (9)0.0048 (9)
C160.0199 (11)0.0321 (12)0.0229 (11)0.0068 (9)0.0020 (9)0.0027 (9)
C170.0181 (11)0.0223 (10)0.0221 (11)0.0063 (8)0.0025 (8)0.0021 (8)
O10.0237 (8)0.0326 (8)0.0279 (8)0.0134 (6)0.0084 (6)0.0044 (6)
N210.0169 (9)0.0217 (9)0.0249 (10)0.0078 (7)0.0061 (7)0.0039 (7)
C210.0226 (11)0.0171 (10)0.0211 (11)0.0057 (8)0.0015 (8)0.0026 (8)
C220.0234 (11)0.0254 (11)0.0227 (11)0.0105 (9)0.0028 (9)0.0031 (8)
C230.0325 (13)0.0292 (11)0.0240 (12)0.0168 (10)0.0002 (10)0.0033 (9)
C240.0413 (14)0.0222 (11)0.0197 (11)0.0123 (10)0.0010 (10)0.0012 (8)
F240.0566 (9)0.0359 (7)0.0300 (8)0.0230 (7)0.0073 (7)0.0111 (6)
C250.0285 (12)0.0275 (12)0.0277 (12)0.0056 (9)0.0081 (10)0.0022 (9)
C260.0233 (12)0.0271 (11)0.0297 (12)0.0086 (9)0.0046 (9)0.0016 (9)
O20.0212 (8)0.0271 (8)0.0357 (9)0.0111 (6)0.0052 (6)0.0057 (6)
Geometric parameters (Å, º) top
N11—C121.325 (3)N21—H210.9217
N11—C161.345 (3)C21—C261.386 (3)
C12—C131.397 (3)C21—C221.394 (3)
C12—Cl11.738 (2)C22—C231.386 (3)
C13—C141.394 (3)C22—H220.95
C13—C171.501 (3)C23—C241.368 (3)
C14—C151.384 (3)C23—H230.95
C14—H140.95C24—C251.367 (3)
C15—C161.381 (3)C24—F241.368 (2)
C15—H150.95C25—C261.389 (3)
C16—H160.95C25—H250.95
C17—O11.235 (2)C26—H260.95
C17—N211.343 (2)O2—H2A0.9508
N21—C211.423 (2)O2—H2B0.8371
C12—N11—C16117.01 (17)C21—N21—H21117.2
N11—C12—C13124.72 (19)C26—C21—C22120.02 (19)
N11—C12—Cl1115.00 (15)C26—C21—N21123.98 (18)
C13—C12—Cl1120.21 (15)C22—C21—N21116.00 (18)
C14—C13—C12116.67 (18)C23—C22—C21120.2 (2)
C14—C13—C17119.78 (18)C23—C22—H22119.9
C12—C13—C17123.38 (18)C21—C22—H22119.9
C15—C14—C13119.74 (19)C24—C23—C22118.3 (2)
C15—C14—H14120.1C24—C23—H23120.9
C13—C14—H14120.1C22—C23—H23120.9
C16—C15—C14118.4 (2)C25—C24—C23123.1 (2)
C16—C15—H15120.8C25—C24—F24118.5 (2)
C14—C15—H15120.8C23—C24—F24118.43 (19)
N11—C16—C15123.42 (19)C24—C25—C26118.8 (2)
N11—C16—H16118.3C24—C25—H25120.6
C15—C16—H16118.3C26—C25—H25120.6
O1—C17—N21125.40 (18)C21—C26—C25119.7 (2)
O1—C17—C13120.50 (17)C21—C26—H26120.2
N21—C17—C13113.99 (17)C25—C26—H26120.2
C17—N21—C21127.79 (17)H2A—O2—H2B112.3
C17—N21—H21114.9
C16—N11—C12—C130.7 (3)O1—C17—N21—C214.9 (3)
C16—N11—C12—Cl1177.79 (14)C13—C17—N21—C21171.39 (18)
N11—C12—C13—C141.4 (3)C17—N21—C21—C265.9 (3)
Cl1—C12—C13—C14175.56 (14)C17—N21—C21—C22174.60 (18)
N11—C12—C13—C17174.01 (18)C26—C21—C22—C231.2 (3)
Cl1—C12—C13—C179.1 (3)N21—C21—C22—C23178.30 (17)
C12—C13—C14—C152.0 (3)C21—C22—C23—C240.7 (3)
C17—C13—C14—C15173.52 (18)C22—C23—C24—C250.4 (3)
C13—C14—C15—C160.7 (3)C22—C23—C24—F24179.80 (18)
C12—N11—C16—C152.2 (3)C23—C24—C25—C261.0 (3)
C14—C15—C16—N111.5 (3)F24—C24—C25—C26179.21 (18)
C14—C13—C17—O1122.2 (2)C22—C21—C26—C250.6 (3)
C12—C13—C17—O153.0 (3)N21—C21—C26—C25178.85 (19)
C14—C13—C17—N2154.2 (2)C24—C25—C26—C210.5 (3)
C12—C13—C17—N21130.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···N11i0.951.972.887 (2)161
O2—H2B···O1ii0.841.952.780 (2)173
N21—H21···O20.921.912.837 (2)179
Symmetry codes: (i) x+1, y+2, z+1; (ii) x1, y, z.
(IV) N-(4-Chlorophenyl-2-chloronicotinamide top
Crystal data top
C12H8Cl2N2OF(000) = 1088
Mr = 267.10Dx = 1.543 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9787 reflections
a = 5.0855 (8) Åθ = 3.0–27.5°
b = 28.982 (8) ŵ = 0.55 mm1
c = 15.607 (4) ÅT = 120 K
β = 90.37 (2)°Plate, colourless
V = 2300.2 (9) Å30.28 × 0.07 × 0.03 mm
Z = 8
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
9787 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode6370 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ & ω scansh = 66
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 3737
Tmin = 0.862, Tmax = 0.984l = 2020
24726 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0454P)2 + 5.774P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
9787 reflectionsΔρmax = 0.79 e Å3
254 parametersΔρmin = 0.54 e Å3
1 restraintAbsolute structure: Flack (1983), 4396 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.54 (11)
Crystal data top
C12H8Cl2N2OV = 2300.2 (9) Å3
Mr = 267.10Z = 8
Monoclinic, P21Mo Kα radiation
a = 5.0855 (8) ŵ = 0.55 mm1
b = 28.982 (8) ÅT = 120 K
c = 15.607 (4) Å0.28 × 0.07 × 0.03 mm
β = 90.37 (2)°
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
9787 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
6370 reflections with I > 2σ(I)
Tmin = 0.862, Tmax = 0.984Rint = 0.053
24726 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.069H-atom parameters constrained
wR(F2) = 0.169Δρmax = 0.79 e Å3
S = 1.04Δρmin = 0.54 e Å3
9787 reflectionsAbsolute structure: Flack (1983), 4396 Friedel pairs
254 parametersAbsolute structure parameter: 0.54 (11)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N111.0930 (11)0.1416 (2)0.0684 (4)0.0249 (6)
C121.1545 (15)0.0970 (3)0.0642 (5)0.0249 (6)
Cl11.3934 (4)0.07776 (6)0.13183 (11)0.0255 (4)
C131.0218 (16)0.0653 (3)0.0091 (5)0.0249 (6)
C140.8354 (15)0.0820 (3)0.0465 (4)0.0249 (6)
C150.7658 (14)0.1313 (3)0.0424 (5)0.0249 (6)
C160.8947 (12)0.1561 (3)0.0104 (4)0.0249 (6)
C171.0824 (14)0.0137 (3)0.0081 (5)0.0249 (6)
O11.3151 (10)0.00037 (17)0.0012 (3)0.0249 (6)
N210.8848 (12)0.0131 (2)0.0071 (4)0.0193 (5)
Cl240.8822 (4)0.21692 (6)0.02990 (14)0.0324 (5)
C210.8859 (7)0.06241 (12)0.0004 (2)0.0193 (5)
C220.6884 (6)0.08819 (14)0.0387 (2)0.0193 (5)
C230.6872 (6)0.13596 (14)0.0308 (2)0.0193 (5)
C240.8835 (7)0.15795 (12)0.0162 (2)0.0193 (5)
C251.0810 (6)0.13216 (14)0.0554 (2)0.0193 (5)
C261.0822 (6)0.08439 (14)0.0474 (2)0.0193 (5)
N310.3668 (10)0.8114 (2)0.1869 (4)0.0231 (5)
C320.4029 (15)0.7668 (3)0.1884 (5)0.0231 (5)
Cl30.6478 (4)0.74925 (6)0.11518 (12)0.0285 (5)
C330.2773 (16)0.7352 (3)0.2393 (5)0.0231 (5)
C340.0798 (15)0.7547 (3)0.2904 (5)0.0231 (5)
C350.0404 (13)0.7987 (2)0.2935 (5)0.0231 (5)
C360.1852 (12)0.8288 (2)0.2357 (4)0.0231 (5)
C370.3454 (14)0.6860 (3)0.2416 (5)0.0231 (5)
O30.5701 (9)0.67153 (16)0.2390 (3)0.0231 (5)
N410.1203 (12)0.6564 (2)0.2434 (4)0.0211 (5)
Cl440.1270 (4)0.45328 (6)0.27721 (12)0.0280 (5)
C410.1364 (7)0.60846 (12)0.2500 (2)0.0211 (5)
C420.0605 (6)0.58283 (15)0.2102 (2)0.0211 (5)
C430.0640 (6)0.53508 (14)0.2184 (2)0.0211 (5)
C440.1295 (7)0.51296 (12)0.2665 (3)0.0211 (5)
C450.3263 (6)0.53858 (14)0.3063 (2)0.0211 (5)
C460.3298 (6)0.58633 (14)0.2981 (2)0.0211 (5)
N510.4263 (11)0.3580 (2)0.5740 (4)0.0252 (6)
C520.3620 (15)0.4025 (3)0.5697 (5)0.0252 (6)
Cl50.1300 (4)0.42136 (6)0.64060 (11)0.0272 (4)
C530.4881 (16)0.4344 (3)0.5147 (5)0.0252 (6)
C540.6738 (15)0.4183 (3)0.4579 (5)0.0252 (6)
C550.7478 (13)0.3695 (2)0.4609 (5)0.0252 (6)
C560.6201 (12)0.3440 (3)0.5145 (4)0.0252 (6)
C570.4242 (14)0.4860 (3)0.5140 (5)0.0252 (6)
O50.1900 (10)0.49896 (17)0.5091 (3)0.0252 (6)
Cl640.5855 (4)0.71624 (6)0.46495 (13)0.0298 (5)
N610.6203 (12)0.5126 (2)0.5135 (4)0.0201 (5)
C610.6177 (7)0.56264 (12)0.5049 (2)0.0201 (5)
C620.8107 (6)0.58460 (14)0.4572 (2)0.0201 (5)
C630.8043 (6)0.63223 (15)0.4470 (2)0.0201 (5)
C640.6049 (7)0.65791 (12)0.4845 (2)0.0201 (5)
C650.4120 (6)0.63595 (15)0.5322 (2)0.0201 (5)
C660.4184 (6)0.58832 (15)0.5424 (2)0.0201 (5)
N711.1553 (11)0.3130 (2)0.3173 (4)0.0249 (6)
C721.1159 (15)0.2685 (3)0.3159 (5)0.0249 (6)
Cl70.8784 (4)0.25131 (6)0.39206 (12)0.0293 (5)
C731.2365 (16)0.2368 (3)0.2649 (5)0.0249 (6)
C741.4280 (15)0.2551 (3)0.2109 (5)0.0249 (6)
C751.4668 (13)0.2994 (2)0.2065 (5)0.0249 (6)
C761.3311 (12)0.3301 (2)0.2677 (4)0.0249 (6)
C771.1627 (14)0.1876 (3)0.2631 (5)0.0249 (6)
O70.9370 (9)0.17332 (16)0.2669 (3)0.0249 (6)
N811.3862 (12)0.1571 (2)0.2606 (4)0.0208 (5)
Cl841.3420 (4)0.04497 (6)0.21810 (13)0.0297 (5)
C811.3679 (7)0.10957 (12)0.2546 (2)0.0208 (5)
C821.5613 (6)0.08769 (14)0.2070 (2)0.0208 (5)
C831.5558 (6)0.04005 (14)0.1969 (2)0.0208 (5)
C841.3569 (7)0.01429 (12)0.2344 (3)0.0208 (5)
C851.1634 (6)0.03616 (15)0.2820 (2)0.0208 (5)
C861.1690 (6)0.08381 (15)0.2921 (2)0.0208 (5)
H140.75330.06210.08660.030*
H150.63150.14400.07720.030*
H160.85330.18810.01090.030*
H210.72940.00010.01160.023*
H220.55420.07320.07090.023*
H230.55220.15360.05750.023*
H251.21520.14720.08750.023*
H261.21720.06680.07420.023*
H340.02800.73490.32360.028*
H350.08150.81130.33300.028*
H360.14730.86080.23370.028*
H410.03660.66900.24010.025*
H420.19270.59800.17730.025*
H430.19850.51760.19120.025*
H450.45850.52350.33920.025*
H460.46440.60380.32530.025*
H540.75210.43850.41760.030*
H550.88200.35730.42550.030*
H560.66120.31210.51400.030*
H610.77560.49950.51890.024*
H620.94690.56700.43150.024*
H630.93620.64720.41440.024*
H650.27570.65350.55790.024*
H660.28650.57330.57500.024*
H741.53120.23490.17690.030*
H751.58090.31190.16460.030*
H761.37330.36200.27030.030*
H811.54410.16950.26290.025*
H821.69730.10530.18130.025*
H831.68800.02510.16430.025*
H851.02750.01860.30770.025*
H861.03680.09880.32470.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0242 (13)0.0245 (15)0.0262 (12)0.0006 (11)0.0013 (10)0.0009 (11)
C120.0242 (13)0.0245 (15)0.0262 (12)0.0006 (11)0.0013 (10)0.0009 (11)
Cl10.0312 (10)0.0205 (10)0.0249 (9)0.0036 (8)0.0083 (7)0.0004 (8)
C130.0242 (13)0.0245 (15)0.0262 (12)0.0006 (11)0.0013 (10)0.0009 (11)
C140.0242 (13)0.0245 (15)0.0262 (12)0.0006 (11)0.0013 (10)0.0009 (11)
C150.0242 (13)0.0245 (15)0.0262 (12)0.0006 (11)0.0013 (10)0.0009 (11)
C160.0242 (13)0.0245 (15)0.0262 (12)0.0006 (11)0.0013 (10)0.0009 (11)
C170.0242 (13)0.0245 (15)0.0262 (12)0.0006 (11)0.0013 (10)0.0009 (11)
O10.0242 (13)0.0245 (15)0.0262 (12)0.0006 (11)0.0013 (10)0.0009 (11)
N210.0169 (11)0.0209 (12)0.0202 (12)0.0001 (10)0.0027 (9)0.0005 (9)
Cl240.0369 (12)0.0165 (11)0.0438 (12)0.0031 (9)0.0072 (9)0.0017 (9)
C210.0169 (11)0.0209 (12)0.0202 (12)0.0001 (10)0.0027 (9)0.0005 (9)
C220.0169 (11)0.0209 (12)0.0202 (12)0.0001 (10)0.0027 (9)0.0005 (9)
C230.0169 (11)0.0209 (12)0.0202 (12)0.0001 (10)0.0027 (9)0.0005 (9)
C240.0169 (11)0.0209 (12)0.0202 (12)0.0001 (10)0.0027 (9)0.0005 (9)
C250.0169 (11)0.0209 (12)0.0202 (12)0.0001 (10)0.0027 (9)0.0005 (9)
C260.0169 (11)0.0209 (12)0.0202 (12)0.0001 (10)0.0027 (9)0.0005 (9)
N310.0225 (12)0.0146 (12)0.0324 (13)0.0002 (10)0.0059 (10)0.0015 (10)
C320.0225 (12)0.0146 (12)0.0324 (13)0.0002 (10)0.0059 (10)0.0015 (10)
Cl30.0264 (10)0.0245 (11)0.0347 (11)0.0019 (9)0.0116 (8)0.0006 (9)
C330.0225 (12)0.0146 (12)0.0324 (13)0.0002 (10)0.0059 (10)0.0015 (10)
C340.0225 (12)0.0146 (12)0.0324 (13)0.0002 (10)0.0059 (10)0.0015 (10)
C350.0225 (12)0.0146 (12)0.0324 (13)0.0002 (10)0.0059 (10)0.0015 (10)
C360.0225 (12)0.0146 (12)0.0324 (13)0.0002 (10)0.0059 (10)0.0015 (10)
C370.0225 (12)0.0146 (12)0.0324 (13)0.0002 (10)0.0059 (10)0.0015 (10)
O30.0225 (12)0.0146 (12)0.0324 (13)0.0002 (10)0.0059 (10)0.0015 (10)
N410.0228 (12)0.0173 (12)0.0233 (12)0.0005 (10)0.0042 (9)0.0003 (10)
Cl440.0373 (12)0.0153 (10)0.0314 (10)0.0023 (8)0.0044 (8)0.0018 (8)
C410.0228 (12)0.0173 (12)0.0233 (12)0.0005 (10)0.0042 (9)0.0003 (10)
C420.0228 (12)0.0173 (12)0.0233 (12)0.0005 (10)0.0042 (9)0.0003 (10)
C430.0228 (12)0.0173 (12)0.0233 (12)0.0005 (10)0.0042 (9)0.0003 (10)
C440.0228 (12)0.0173 (12)0.0233 (12)0.0005 (10)0.0042 (9)0.0003 (10)
C450.0228 (12)0.0173 (12)0.0233 (12)0.0005 (10)0.0042 (9)0.0003 (10)
C460.0228 (12)0.0173 (12)0.0233 (12)0.0005 (10)0.0042 (9)0.0003 (10)
N510.0209 (13)0.0243 (15)0.0304 (13)0.0018 (10)0.0007 (10)0.0006 (11)
C520.0209 (13)0.0243 (15)0.0304 (13)0.0018 (10)0.0007 (10)0.0006 (11)
Cl50.0313 (10)0.0197 (10)0.0308 (10)0.0008 (9)0.0123 (8)0.0001 (9)
C530.0209 (13)0.0243 (15)0.0304 (13)0.0018 (10)0.0007 (10)0.0006 (11)
C540.0209 (13)0.0243 (15)0.0304 (13)0.0018 (10)0.0007 (10)0.0006 (11)
C550.0209 (13)0.0243 (15)0.0304 (13)0.0018 (10)0.0007 (10)0.0006 (11)
C560.0209 (13)0.0243 (15)0.0304 (13)0.0018 (10)0.0007 (10)0.0006 (11)
C570.0209 (13)0.0243 (15)0.0304 (13)0.0018 (10)0.0007 (10)0.0006 (11)
O50.0209 (13)0.0243 (15)0.0304 (13)0.0018 (10)0.0007 (10)0.0006 (11)
Cl640.0330 (11)0.0164 (10)0.0400 (11)0.0020 (8)0.0040 (9)0.0033 (8)
N610.0169 (11)0.0228 (13)0.0207 (12)0.0021 (10)0.0004 (9)0.0001 (10)
C610.0169 (11)0.0228 (13)0.0207 (12)0.0021 (10)0.0004 (9)0.0001 (10)
C620.0169 (11)0.0228 (13)0.0207 (12)0.0021 (10)0.0004 (9)0.0001 (10)
C630.0169 (11)0.0228 (13)0.0207 (12)0.0021 (10)0.0004 (9)0.0001 (10)
C640.0169 (11)0.0228 (13)0.0207 (12)0.0021 (10)0.0004 (9)0.0001 (10)
C650.0169 (11)0.0228 (13)0.0207 (12)0.0021 (10)0.0004 (9)0.0001 (10)
C660.0169 (11)0.0228 (13)0.0207 (12)0.0021 (10)0.0004 (9)0.0001 (10)
N710.0249 (13)0.0151 (13)0.0347 (13)0.0005 (10)0.0085 (10)0.0005 (10)
C720.0249 (13)0.0151 (13)0.0347 (13)0.0005 (10)0.0085 (10)0.0005 (10)
Cl70.0345 (11)0.0208 (10)0.0328 (10)0.0023 (9)0.0145 (8)0.0038 (8)
C730.0249 (13)0.0151 (13)0.0347 (13)0.0005 (10)0.0085 (10)0.0005 (10)
C740.0249 (13)0.0151 (13)0.0347 (13)0.0005 (10)0.0085 (10)0.0005 (10)
C750.0249 (13)0.0151 (13)0.0347 (13)0.0005 (10)0.0085 (10)0.0005 (10)
C760.0249 (13)0.0151 (13)0.0347 (13)0.0005 (10)0.0085 (10)0.0005 (10)
C770.0249 (13)0.0151 (13)0.0347 (13)0.0005 (10)0.0085 (10)0.0005 (10)
O70.0249 (13)0.0151 (13)0.0347 (13)0.0005 (10)0.0085 (10)0.0005 (10)
N810.0216 (12)0.0169 (12)0.0239 (12)0.0014 (10)0.0002 (9)0.0019 (9)
Cl840.0394 (12)0.0163 (10)0.0335 (10)0.0024 (9)0.0101 (9)0.0031 (8)
C810.0216 (12)0.0169 (12)0.0239 (12)0.0014 (10)0.0002 (9)0.0019 (9)
C820.0216 (12)0.0169 (12)0.0239 (12)0.0014 (10)0.0002 (9)0.0019 (9)
C830.0216 (12)0.0169 (12)0.0239 (12)0.0014 (10)0.0002 (9)0.0019 (9)
C840.0216 (12)0.0169 (12)0.0239 (12)0.0014 (10)0.0002 (9)0.0019 (9)
C850.0216 (12)0.0169 (12)0.0239 (12)0.0014 (10)0.0002 (9)0.0019 (9)
C860.0216 (12)0.0169 (12)0.0239 (12)0.0014 (10)0.0002 (9)0.0019 (9)
Geometric parameters (Å, º) top
N11—C121.330 (10)N51—C521.330 (10)
N11—C161.424 (9)N51—C561.418 (9)
C12—C131.432 (12)C52—C531.418 (12)
C12—Cl11.709 (8)C52—Cl51.713 (8)
C13—C141.376 (11)C53—C541.382 (11)
C13—C171.525 (11)C53—C571.530 (11)
C14—C151.474 (11)C54—C551.462 (11)
C14—H140.95C54—H540.95
C15—C161.278 (10)C55—C561.295 (10)
C15—H150.95C55—H550.95
C16—H160.95C56—H560.95
C17—O11.249 (9)C57—O51.251 (9)
C17—N211.270 (9)C57—N611.260 (9)
N21—C211.435 (7)Cl64—C641.721 (4)
N21—H210.88N61—C611.456 (7)
Cl24—C241.722 (4)N61—H610.88
C21—C221.39C61—C621.39
C21—C261.39C61—C661.39
C22—C231.39C62—C631.39
C22—H220.95C62—H620.95
C23—C241.39C63—C641.39
C23—H230.95C63—H630.95
C24—C251.39C64—C651.39
C25—C261.39C65—C661.39
C25—H250.95C65—H650.95
C26—H260.95C66—H660.95
N31—C361.302 (8)N71—C761.285 (9)
N31—C321.307 (10)N71—C721.305 (10)
C32—C331.372 (11)C72—C731.365 (11)
C32—Cl31.770 (8)C72—Cl71.771 (8)
C33—C341.405 (11)C73—C741.396 (11)
C33—C371.469 (10)C73—C771.474 (11)
C34—C351.290 (11)C74—C751.300 (11)
C34—H340.95C74—H740.95
C35—C361.458 (9)C75—C761.479 (10)
C35—H350.95C75—H750.95
C36—H360.95C76—H760.95
C37—O31.218 (8)C77—O71.222 (8)
C37—N411.431 (9)C77—N811.441 (9)
N41—C411.394 (7)N81—C811.384 (7)
N41—H410.88N81—H810.88
Cl44—C441.738 (4)Cl84—C841.738 (4)
C41—C421.39C81—C821.39
C41—C461.39C81—C861.39
C42—C431.39C82—C831.39
C42—H420.95C82—H820.95
C43—C441.39C83—C841.39
C43—H430.95C83—H830.95
C44—C451.39C84—C851.39
C45—C461.39C85—C861.39
C45—H450.95C85—H850.95
C46—H460.95C86—H860.95
C12—N11—C16115.0 (6)C52—N51—C56114.5 (6)
N11—C12—C13122.9 (7)N51—C52—C53123.4 (7)
N11—C12—Cl1117.0 (6)N51—C52—Cl5116.5 (6)
C13—C12—Cl1120.0 (6)C53—C52—Cl5119.9 (6)
C14—C13—C12118.8 (8)C54—C53—C52118.7 (8)
C14—C13—C17118.5 (7)C54—C53—C57118.2 (7)
C12—C13—C17122.7 (7)C52—C53—C57123.1 (7)
C13—C14—C15118.7 (7)C53—C54—C55118.9 (7)
C13—C14—H14120.7C53—C54—H54120.5
C15—C14—H14120.7C55—C54—H54120.5
C16—C15—C14116.8 (7)C56—C55—C54116.2 (7)
C16—C15—H15121.6C56—C55—H55121.9
C14—C15—H15121.6C54—C55—H55121.9
C15—C16—N11127.7 (7)C55—C56—N51127.9 (7)
C15—C16—H16116.2C55—C56—H56116.1
N11—C16—H16116.2N51—C56—H56116.1
O1—C17—N21124.0 (8)O5—C57—N61124.7 (8)
O1—C17—C13119.7 (7)O5—C57—C53119.7 (7)
N21—C17—C13116.0 (7)N61—C57—C53115.4 (7)
C17—N21—C21127.4 (6)C57—N61—C61127.1 (6)
C17—N21—H21116.3C57—N61—H61116.5
C21—N21—H21116.3C61—N61—H61116.5
C22—C21—C26120.0C62—C61—C66120.0
C22—C21—N21119.8 (3)C62—C61—N61120.0 (3)
C26—C21—N21120.2 (3)C66—C61—N61120.0 (3)
C21—C22—C23120.0C61—C62—C63120.0
C21—C22—H22120.0C61—C62—H62120.0
C23—C22—H22120.0C63—C62—H62120.0
C24—C23—C22120.0C64—C63—C62120.0
C24—C23—H23120.0C64—C63—H63120.0
C22—C23—H23120.0C62—C63—H63120.0
C25—C24—C23120.0C65—C64—C63120.0
C25—C24—Cl24118.8 (2)C65—C64—Cl64120.3 (2)
C23—C24—Cl24121.1 (2)C63—C64—Cl64119.5 (2)
C24—C25—C26120.0C66—C65—C64120.0
C24—C25—H25120.0C66—C65—H65120.0
C26—C25—H25120.0C64—C65—H65120.0
C25—C26—C21120.0C65—C66—C61120.0
C25—C26—H26120.0C65—C66—H66120.0
C21—C26—H26120.0C61—C66—H66120.0
C36—N31—C32118.2 (6)C76—N71—C72118.6 (7)
N31—C32—C33127.1 (7)N71—C72—C73127.2 (8)
N31—C32—Cl3111.9 (6)N71—C72—Cl7111.9 (6)
C33—C32—Cl3121.0 (6)C73—C72—Cl7120.9 (6)
C32—C33—C34113.4 (7)C72—C73—C74114.5 (7)
C32—C33—C37123.5 (7)C72—C73—C77123.1 (7)
C34—C33—C37123.1 (7)C74—C73—C77122.3 (7)
C35—C34—C33122.0 (8)C75—C74—C73120.8 (8)
C35—C34—H34119.0C75—C74—H74119.6
C33—C34—H34119.0C73—C74—H74119.6
C34—C35—C36119.2 (7)C74—C75—C76119.3 (7)
C34—C35—H35120.4C74—C75—H75120.4
C36—C35—H35120.4C76—C75—H75120.4
N31—C36—C35119.6 (6)N71—C76—C75119.0 (6)
N31—C36—H36120.2N71—C76—H76120.5
C35—C36—H36120.2C75—C76—H76120.5
O3—C37—N41123.0 (7)O7—C77—N81122.3 (7)
O3—C37—C33123.6 (7)O7—C77—C73124.5 (7)
N41—C37—C33113.3 (6)N81—C77—C73113.1 (6)
C41—N41—C37123.5 (6)C81—N81—C77124.1 (6)
C41—N41—H41118.2C81—N81—H81118.0
C37—N41—H41118.2C77—N81—H81118.0
C42—C41—C46120.0N81—C81—C82116.3 (3)
C42—C41—N41117.2 (3)N81—C81—C86123.7 (3)
C46—C41—N41122.7 (3)C82—C81—C86120.0
C43—C42—C41120.0C81—C82—C83120.0
C43—C42—H42120.0C81—C82—H82120.0
C41—C42—H42120.0C83—C82—H82120.0
C42—C43—C44120.0C84—C83—C82120.0
C42—C43—H43120.0C84—C83—H83120.0
C44—C43—H43120.0C82—C83—H83120.0
C45—C44—C43120.0C83—C84—C85120.0
C45—C44—Cl44119.6 (2)C83—C84—Cl84120.0 (2)
C43—C44—Cl44120.4 (2)C85—C84—Cl84119.9 (2)
C44—C45—C46120.0C84—C85—C86120.0
C44—C45—H45120.0C84—C85—H85120.0
C46—C45—H45120.0C86—C85—H85120.0
C45—C46—C41120.0C85—C86—C81120.0
C45—C46—H46120.0C85—C86—H86120.0
C41—C46—H46120.0C81—C86—H86120.0
C16—N11—C12—C133.4 (10)C56—N51—C52—C534.3 (10)
C16—N11—C12—Cl1179.5 (5)C56—N51—C52—Cl5179.6 (5)
N11—C12—C13—C144.8 (11)N51—C52—C53—C545.1 (12)
Cl1—C12—C13—C14178.2 (5)Cl5—C52—C53—C54179.8 (6)
N11—C12—C13—C17176.5 (7)N51—C52—C53—C57176.2 (6)
Cl1—C12—C13—C170.5 (10)Cl5—C52—C53—C571.1 (10)
C12—C13—C14—C154.6 (10)C52—C53—C54—C554.6 (11)
C17—C13—C14—C15176.7 (6)C57—C53—C54—C55176.7 (6)
C13—C14—C15—C163.5 (10)C53—C54—C55—C563.9 (10)
C14—C15—C16—N112.4 (10)C54—C55—C56—N513.6 (10)
C12—N11—C16—C152.5 (10)C52—N51—C56—C553.8 (10)
C14—C13—C17—O1128.4 (8)C54—C53—C57—O5129.1 (8)
C12—C13—C17—O150.3 (10)C52—C53—C57—O549.6 (11)
C14—C13—C17—N2145.8 (9)C54—C53—C57—N6146.9 (10)
C12—C13—C17—N21135.5 (8)C52—C53—C57—N61134.4 (8)
O1—C17—N21—C211.0 (12)O5—C57—N61—C611.8 (12)
C13—C17—N21—C21175.0 (6)C53—C57—N61—C61173.9 (6)
C17—N21—C21—C22149.0 (6)C57—N61—C61—C62141.9 (6)
C17—N21—C21—C2631.7 (8)C57—N61—C61—C6636.4 (8)
C26—C21—C22—C230.0C66—C61—C62—C630.0
N21—C21—C22—C23179.3 (4)N61—C61—C62—C63178.2 (4)
C21—C22—C23—C240.0C61—C62—C63—C640.0
C22—C23—C24—C250.0C62—C63—C64—C650.0
C22—C23—C24—Cl24178.1 (3)C62—C63—C64—Cl64175.3 (3)
C23—C24—C25—C260.0C63—C64—C65—C660.0
Cl24—C24—C25—C26178.1 (3)Cl64—C64—C65—C66175.2 (3)
C24—C25—C26—C210.0C64—C65—C66—C610.0
C22—C21—C26—C250.0C62—C61—C66—C650.0
N21—C21—C26—C25179.3 (4)N61—C61—C66—C65178.2 (4)
C36—N31—C32—C333.2 (11)C76—N71—C72—C732.2 (12)
C36—N31—C32—Cl3177.7 (5)C76—N71—C72—Cl7177.1 (5)
N31—C32—C33—C344.0 (12)N71—C72—C73—C742.2 (12)
Cl3—C32—C33—C34177.0 (5)Cl7—C72—C73—C74177.1 (6)
N31—C32—C33—C37174.9 (7)N71—C72—C73—C77174.8 (7)
Cl3—C32—C33—C374.1 (11)Cl7—C72—C73—C775.9 (11)
C32—C33—C34—C355.8 (11)C72—C73—C74—C755.3 (11)
C37—C33—C34—C35173.1 (7)C77—C73—C74—C75171.7 (7)
C33—C34—C35—C366.7 (11)C73—C74—C75—C768.1 (11)
C32—N31—C36—C353.6 (9)C72—N71—C76—C754.7 (10)
C34—C35—C36—N315.6 (10)C74—C75—C76—N717.9 (10)
C32—C33—C37—O339.5 (12)C72—C73—C77—O739.2 (12)
C34—C33—C37—O3139.3 (8)C74—C73—C77—O7137.6 (8)
C32—C33—C37—N41137.9 (8)C72—C73—C77—N81138.0 (8)
C34—C33—C37—N4143.3 (10)C74—C73—C77—N8145.2 (10)
O3—C37—N41—C415.9 (11)O7—C77—N81—C815.8 (11)
C33—C37—N41—C41176.7 (6)C73—C77—N81—C81176.9 (6)
C37—N41—C41—C42148.6 (5)C77—N81—C81—C82144.9 (5)
C37—N41—C41—C4635.1 (7)C77—N81—C81—C8634.2 (8)
C46—C41—C42—C430.0N81—C81—C82—C83179.2 (4)
N41—C41—C42—C43176.4 (4)C86—C81—C82—C830.0
C41—C42—C43—C440.0C81—C82—C83—C840.0
C42—C43—C44—C450.0C82—C83—C84—C850.0
C42—C43—C44—Cl44180.0 (3)C82—C83—C84—Cl84177.3 (3)
C43—C44—C45—C460.0C83—C84—C85—C860.0
Cl44—C44—C45—C46180.0 (3)Cl84—C84—C85—C86177.3 (3)
C44—C45—C46—C410.0C84—C85—C86—C810.0
C42—C41—C46—C450.0N81—C81—C86—C85179.2 (5)
N41—C41—C46—C45176.2 (5)C82—C81—C86—C850.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O1i0.882.112.925 (8)153
N41—H41···O3i0.882.002.833 (8)157
N61—H61···O5ii0.882.112.925 (8)153
N81—H81···O7ii0.882.002.841 (8)159
C26—H26···Cg50.952.763.444 (8)130
C46—H46···Cg40.952.753.448 (8)131
C62—H62···Cg3ii0.952.883.588 (8)132
C82—H82···Cg2ii0.952.873.579 (8)132
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
(V) N-(4-bromophenyl)-2-chloronicotinamide top
Crystal data top
C12H8BrClN2OF(000) = 616
Mr = 311.56Dx = 1.727 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2736 reflections
a = 4.8810 (2) Åθ = 3.1–27.5°
b = 13.3448 (2) ŵ = 3.64 mm1
c = 18.3974 (3) ÅT = 120 K
V = 1198.33 (6) Å3Block, colourless
Z = 40.16 × 0.16 × 0.16 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2736 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2597 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ & ω scansh = 66
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1717
Tmin = 0.558, Tmax = 0.558l = 2323
36201 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.060 w = 1/[σ2(Fo2) + (0.0339P)2 + 0.2964P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
2736 reflectionsΔρmax = 0.43 e Å3
154 parametersΔρmin = 0.52 e Å3
0 restraintsAbsolute structure: Flack (1983), 1098 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.031 (7)
Crystal data top
C12H8BrClN2OV = 1198.33 (6) Å3
Mr = 311.56Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.8810 (2) ŵ = 3.64 mm1
b = 13.3448 (2) ÅT = 120 K
c = 18.3974 (3) Å0.16 × 0.16 × 0.16 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2736 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2597 reflections with I > 2σ(I)
Tmin = 0.558, Tmax = 0.558Rint = 0.047
36201 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.060Δρmax = 0.43 e Å3
S = 1.07Δρmin = 0.52 e Å3
2736 reflectionsAbsolute structure: Flack (1983), 1098 Friedel pairs
154 parametersAbsolute structure parameter: 0.031 (7)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.2251 (4)0.44892 (15)0.25022 (11)0.0305 (4)
C120.3184 (4)0.53761 (16)0.27104 (11)0.0233 (4)
Cl10.20925 (12)0.63776 (4)0.21708 (3)0.03344 (13)
C130.5004 (4)0.55387 (15)0.32813 (11)0.0212 (4)
C140.6017 (5)0.46884 (16)0.36219 (12)0.0282 (5)
C150.5092 (5)0.37504 (17)0.34193 (13)0.0350 (5)
C160.3191 (5)0.36907 (17)0.28653 (13)0.0344 (5)
C170.5980 (4)0.65411 (16)0.35532 (10)0.0218 (4)
O10.8431 (3)0.66775 (13)0.36577 (10)0.0359 (4)
N210.4029 (3)0.72119 (12)0.37036 (9)0.0212 (3)
C210.4464 (4)0.81970 (14)0.39778 (10)0.0201 (4)
C220.2741 (4)0.89596 (16)0.37318 (12)0.0261 (4)
C230.3060 (5)0.99245 (16)0.39955 (12)0.0275 (5)
C240.5085 (4)1.01185 (14)0.44999 (11)0.0242 (4)
Br240.55925 (5)1.144725 (15)0.484926 (12)0.03552 (8)
C250.6793 (4)0.93690 (16)0.47524 (11)0.0256 (4)
C260.6465 (4)0.83994 (16)0.44923 (11)0.0236 (4)
H140.73510.47510.39950.037*
H150.57460.31630.36540.045*
H160.25120.30480.27350.045*
H210.24660.70570.36310.025*
H220.13550.88170.33850.034*
H230.18951.04480.38310.036*
H250.81760.95160.51000.033*
H260.76090.78760.46660.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0325 (10)0.0286 (10)0.0305 (10)0.0047 (8)0.0013 (8)0.0098 (8)
C120.0242 (10)0.0250 (10)0.0206 (10)0.0007 (8)0.0021 (8)0.0028 (8)
Cl10.0459 (3)0.0307 (3)0.0237 (2)0.0034 (3)0.0106 (2)0.0017 (2)
C130.0205 (9)0.0238 (10)0.0192 (9)0.0000 (7)0.0044 (7)0.0029 (8)
C140.0332 (11)0.0288 (11)0.0225 (10)0.0030 (9)0.0007 (9)0.0021 (8)
C150.0501 (14)0.0249 (11)0.0299 (11)0.0034 (10)0.0038 (10)0.0000 (9)
C160.0425 (12)0.0213 (11)0.0393 (13)0.0059 (10)0.0090 (10)0.0085 (10)
C170.0199 (9)0.0259 (10)0.0196 (9)0.0037 (9)0.0019 (7)0.0015 (8)
O10.0187 (7)0.0393 (10)0.0497 (10)0.0021 (7)0.0010 (7)0.0161 (8)
N210.0178 (8)0.0224 (8)0.0232 (8)0.0042 (7)0.0028 (7)0.0034 (7)
C210.0204 (9)0.0206 (9)0.0192 (9)0.0027 (8)0.0016 (8)0.0006 (7)
C220.0243 (10)0.0297 (11)0.0243 (10)0.0003 (9)0.0049 (8)0.0007 (8)
C230.0286 (11)0.0245 (10)0.0293 (12)0.0040 (9)0.0009 (9)0.0017 (9)
C240.0340 (12)0.0175 (9)0.0210 (9)0.0035 (8)0.0055 (8)0.0006 (7)
Br240.05752 (15)0.01955 (11)0.02950 (12)0.00444 (10)0.00210 (10)0.00290 (9)
C250.0284 (10)0.0255 (10)0.0228 (10)0.0042 (8)0.0060 (8)0.0025 (8)
C260.0247 (9)0.0235 (10)0.0225 (9)0.0016 (8)0.0045 (8)0.0004 (8)
Geometric parameters (Å, º) top
N11—C121.325 (3)N21—C211.424 (2)
N11—C161.339 (3)N21—H210.8017
C12—C131.393 (3)C21—C261.387 (3)
C12—Cl11.748 (2)C21—C221.395 (3)
C13—C141.387 (3)C22—C231.385 (3)
C13—C171.506 (3)C22—H220.95
C14—C151.382 (3)C23—C241.381 (3)
C14—H140.95C23—H230.95
C15—C161.381 (4)C24—C251.382 (3)
C15—H150.95C24—Br241.9022 (19)
C16—H160.95C25—C261.389 (3)
C17—O11.225 (3)C25—H250.95
C17—N211.336 (3)C26—H260.95
C12—N11—C16116.70 (19)C17—N21—H21118.1
N11—C12—C13125.2 (2)C21—N21—H21116.0
N11—C12—Cl1114.47 (16)C26—C21—C22120.24 (19)
C13—C12—Cl1120.23 (17)C26—C21—N21121.77 (18)
C14—C13—C12116.14 (19)C22—C21—N21117.95 (18)
C14—C13—C17117.63 (17)C23—C22—C21119.8 (2)
C12—C13—C17126.23 (19)C23—C22—H22120.1
C15—C14—C13120.2 (2)C21—C22—H22120.1
C15—C14—H14119.9C24—C23—C22119.3 (2)
C13—C14—H14119.9C24—C23—H23120.3
C16—C15—C14118.1 (2)C22—C23—H23120.3
C16—C15—H15120.9C23—C24—C25121.47 (19)
C14—C15—H15120.9C23—C24—Br24119.68 (16)
N11—C16—C15123.5 (2)C25—C24—Br24118.84 (16)
N11—C16—H16118.2C24—C25—C26119.25 (19)
C15—C16—H16118.2C24—C25—H25120.4
O1—C17—N21124.3 (2)C26—C25—H25120.4
O1—C17—C13119.55 (18)C21—C26—C25119.86 (19)
N21—C17—C13116.01 (16)C21—C26—H26120.1
C17—N21—C21125.86 (17)C25—C26—H26120.1
C16—N11—C12—C131.3 (3)O1—C17—N21—C212.7 (3)
C16—N11—C12—Cl1175.22 (17)C13—C17—N21—C21178.86 (17)
N11—C12—C13—C144.1 (3)C17—N21—C21—C2638.6 (3)
Cl1—C12—C13—C14172.30 (16)C17—N21—C21—C22143.6 (2)
N11—C12—C13—C17176.62 (19)C26—C21—C22—C230.9 (3)
Cl1—C12—C13—C177.0 (3)N21—C21—C22—C23178.7 (2)
C12—C13—C14—C153.8 (3)C21—C22—C23—C240.0 (3)
C17—C13—C14—C15176.82 (19)C22—C23—C24—C250.5 (3)
C13—C14—C15—C161.1 (3)C22—C23—C24—Br24178.60 (17)
C12—N11—C16—C151.7 (3)C23—C24—C25—C260.0 (3)
C14—C15—C16—N111.8 (4)Br24—C24—C25—C26179.05 (16)
C14—C13—C17—O146.9 (3)C22—C21—C26—C251.3 (3)
C12—C13—C17—O1132.4 (2)N21—C21—C26—C25179.10 (19)
C14—C13—C17—N21129.4 (2)C24—C25—C26—C210.9 (3)
C12—C13—C17—N2151.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O1i0.802.032.825 (2)169
C22—H22···N11ii0.952.563.405 (3)148
Symmetry codes: (i) x1, y, z; (ii) x, y+1/2, z+1/2.
(VI) N-(4-Iodophenyl)-2-chloronicotinamide top
Crystal data top
C12H8ClIN2OF(000) = 1376
Mr = 358.55Dx = 1.868 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2909 reflections
a = 10.6597 (2) Åθ = 3.0–27.5°
b = 25.9833 (3) ŵ = 2.71 mm1
c = 9.2044 (6) ÅT = 120 K
V = 2549.38 (18) Å3Plate, colourless
Z = 80.33 × 0.18 × 0.07 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2909 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2314 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.0°
ϕ & ω scansh = 1313
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 3233
Tmin = 0.469, Tmax = 0.833l = 1111
19649 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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.026P)2 + 0.5926P]
where P = (Fo2 + 2Fc2)/3
2909 reflections(Δ/σ)max = 0.005
154 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.78 e Å3
Crystal data top
C12H8ClIN2OV = 2549.38 (18) Å3
Mr = 358.55Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 10.6597 (2) ŵ = 2.71 mm1
b = 25.9833 (3) ÅT = 120 K
c = 9.2044 (6) Å0.33 × 0.18 × 0.07 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2909 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2314 reflections with I > 2σ(I)
Tmin = 0.469, Tmax = 0.833Rint = 0.038
19649 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.056H-atom parameters constrained
S = 1.04Δρmax = 0.39 e Å3
2909 reflectionsΔρmin = 0.78 e Å3
154 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.60356 (18)0.11949 (7)0.62709 (19)0.0203 (4)
C120.6165 (2)0.16921 (8)0.6038 (2)0.0160 (5)
Cl10.76816 (5)0.19337 (2)0.62506 (6)0.02158 (13)
C130.5212 (2)0.20242 (8)0.5592 (2)0.0143 (4)
C140.4040 (2)0.18113 (8)0.5380 (2)0.0203 (5)
C150.3866 (2)0.12909 (8)0.5640 (2)0.0244 (5)
C160.4878 (2)0.10011 (8)0.6066 (3)0.0245 (5)
C170.54567 (19)0.25827 (8)0.5278 (2)0.0149 (4)
O10.55314 (15)0.27425 (5)0.40199 (16)0.0207 (4)
N210.55734 (17)0.28802 (7)0.64672 (17)0.0170 (4)
C210.5942 (2)0.34079 (8)0.6469 (2)0.0171 (5)
C220.6810 (2)0.35646 (8)0.7503 (2)0.0204 (5)
C230.7200 (2)0.40740 (8)0.7567 (3)0.0220 (5)
C240.6721 (2)0.44248 (8)0.6580 (2)0.0190 (5)
I240.741430 (14)0.518368 (5)0.656374 (16)0.02235 (7)
C250.5848 (2)0.42725 (8)0.5546 (2)0.0195 (5)
C260.5448 (2)0.37637 (8)0.5492 (2)0.0186 (5)
H140.33610.20190.50590.026*
H150.30630.11380.55260.032*
H160.47540.06430.62260.032*
H210.54090.27380.73130.022*
H220.71400.33210.81720.027*
H230.77880.41810.82800.029*
H250.55240.45160.48750.025*
H260.48420.36600.47950.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0209 (11)0.0147 (10)0.0253 (10)0.0018 (8)0.0015 (8)0.0022 (8)
C120.0160 (12)0.0168 (12)0.0150 (11)0.0013 (9)0.0016 (9)0.0029 (9)
Cl10.0157 (3)0.0203 (3)0.0288 (3)0.0014 (2)0.0015 (2)0.0029 (2)
C130.0191 (12)0.0134 (11)0.0105 (10)0.0016 (9)0.0021 (9)0.0010 (8)
C140.0192 (12)0.0188 (12)0.0230 (12)0.0011 (9)0.0050 (10)0.0009 (9)
C150.0209 (13)0.0189 (13)0.0334 (14)0.0057 (10)0.0023 (11)0.0028 (10)
C160.0290 (15)0.0146 (12)0.0300 (13)0.0048 (10)0.0029 (11)0.0007 (10)
C170.0100 (11)0.0154 (11)0.0193 (12)0.0005 (8)0.0004 (9)0.0000 (9)
O10.0329 (10)0.0161 (8)0.0132 (8)0.0007 (7)0.0016 (7)0.0012 (6)
N210.0265 (11)0.0115 (9)0.0131 (9)0.0038 (8)0.0026 (8)0.0005 (7)
C210.0208 (12)0.0146 (11)0.0158 (11)0.0007 (9)0.0039 (9)0.0015 (9)
C220.0305 (14)0.0171 (11)0.0137 (10)0.0002 (10)0.0010 (10)0.0015 (9)
C230.0304 (14)0.0174 (12)0.0182 (11)0.0048 (10)0.0026 (10)0.0036 (9)
C240.0241 (13)0.0096 (11)0.0234 (12)0.0018 (9)0.0059 (10)0.0032 (9)
I240.02689 (11)0.01153 (10)0.02863 (11)0.00335 (6)0.00034 (7)0.00170 (6)
C250.0185 (12)0.0138 (11)0.0263 (12)0.0028 (9)0.0003 (10)0.0024 (9)
C260.0162 (12)0.0173 (11)0.0225 (12)0.0003 (9)0.0005 (9)0.0016 (9)
Geometric parameters (Å, º) top
N11—C121.317 (3)N21—C211.426 (3)
N11—C161.346 (3)N21—H210.88
C12—C131.395 (3)C21—C221.389 (3)
C12—Cl11.745 (2)C21—C261.393 (3)
C13—C141.380 (3)C22—C231.388 (3)
C13—C171.502 (3)C22—H220.95
C14—C151.386 (3)C23—C241.384 (3)
C14—H140.95C23—H230.95
C15—C161.373 (3)C24—C251.388 (3)
C15—H150.95C24—I242.106 (2)
C16—H160.95C25—C261.390 (3)
C17—O11.232 (2)C25—H250.95
C17—N211.346 (3)C26—H260.95
C12—N11—C16116.14 (19)C17—N21—H21117.3
N11—C12—C13125.3 (2)C21—N21—H21117.3
N11—C12—Cl1115.59 (16)C22—C21—C26120.0 (2)
C13—C12—Cl1119.03 (16)C22—C21—N21117.77 (19)
C14—C13—C12116.93 (19)C26—C21—N21122.2 (2)
C14—C13—C17121.16 (18)C23—C22—C21120.5 (2)
C12—C13—C17121.83 (19)C23—C22—H22119.7
C13—C14—C15119.2 (2)C21—C22—H22119.7
C13—C14—H14120.4C24—C23—C22119.3 (2)
C15—C14—H14120.4C24—C23—H23120.3
C16—C15—C14118.6 (2)C22—C23—H23120.3
C16—C15—H15120.7C23—C24—C25120.6 (2)
C14—C15—H15120.7C23—C24—I24119.47 (16)
N11—C16—C15123.7 (2)C25—C24—I24119.83 (16)
N11—C16—H16118.1C24—C25—C26120.1 (2)
C15—C16—H16118.1C24—C25—H25119.9
O1—C17—N21124.37 (19)C26—C25—H25119.9
O1—C17—C13121.16 (18)C25—C26—C21119.5 (2)
N21—C17—C13114.47 (18)C25—C26—H26120.3
C17—N21—C21125.33 (18)C21—C26—H26120.3
C16—N11—C12—C130.6 (3)O1—C17—N21—C217.7 (3)
C16—N11—C12—Cl1178.02 (16)C13—C17—N21—C21172.75 (19)
N11—C12—C13—C140.0 (3)C17—N21—C21—C22135.9 (2)
Cl1—C12—C13—C14177.36 (15)C17—N21—C21—C2645.1 (3)
N11—C12—C13—C17176.83 (19)C26—C21—C22—C230.5 (3)
Cl1—C12—C13—C170.5 (3)N21—C21—C22—C23179.6 (2)
C12—C13—C14—C151.1 (3)C21—C22—C23—C240.5 (3)
C17—C13—C14—C15177.99 (19)C22—C23—C24—C250.8 (3)
C13—C14—C15—C161.6 (3)C22—C23—C24—I24175.18 (16)
C12—N11—C16—C150.0 (3)C23—C24—C25—C260.1 (3)
C14—C15—C16—N111.1 (4)I24—C24—C25—C26175.85 (16)
C14—C13—C17—O173.6 (3)C24—C25—C26—C210.9 (3)
C12—C13—C17—O1103.1 (2)C22—C21—C26—C251.2 (3)
C14—C13—C17—N21106.0 (2)N21—C21—C26—C25179.80 (19)
C12—C13—C17—N2177.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O1i0.882.012.853 (2)160
C15—H15···Cg2ii0.952.653.404 (2)137
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x2, y+1, z.
(VII) N-(4-Methoxyphenyl)-2-chloronicotinamide top
Crystal data top
C13H11ClN2O2F(000) = 544
Mr = 262.69Dx = 1.441 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2661 reflections
a = 4.8536 (2) Åθ = 3.6–27.5°
b = 11.8437 (4) ŵ = 0.31 mm1
c = 21.0612 (7) ÅT = 120 K
V = 1210.69 (6) Å3Block, colourless
Z = 40.34 × 0.22 × 0.12 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2661 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2184 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.6°
ϕ & ω scansh = 56
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1511
Tmin = 0.921, Tmax = 0.964l = 2127
7884 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0579P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2661 reflectionsΔρmax = 0.24 e Å3
164 parametersΔρmin = 0.35 e Å3
0 restraintsAbsolute structure: Flack (1983), 1013 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (7)
Crystal data top
C13H11ClN2O2V = 1210.69 (6) Å3
Mr = 262.69Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.8536 (2) ŵ = 0.31 mm1
b = 11.8437 (4) ÅT = 120 K
c = 21.0612 (7) Å0.34 × 0.22 × 0.12 mm
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
2661 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2184 reflections with I > 2σ(I)
Tmin = 0.921, Tmax = 0.964Rint = 0.040
7884 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.104Δρmax = 0.24 e Å3
S = 1.04Δρmin = 0.35 e Å3
2661 reflectionsAbsolute structure: Flack (1983), 1013 Friedel pairs
164 parametersAbsolute structure parameter: 0.05 (7)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.2528 (4)0.42072 (18)0.20676 (9)0.0307 (5)
C120.3347 (4)0.3434 (2)0.24770 (10)0.0227 (5)
Cl10.56547 (12)0.24507 (5)0.21709 (3)0.03297 (19)
C130.2436 (4)0.33534 (18)0.31091 (9)0.0177 (5)
C140.0515 (4)0.41567 (19)0.33018 (10)0.0208 (5)
C150.0354 (5)0.4982 (2)0.28822 (11)0.0267 (5)
C160.0687 (5)0.4970 (2)0.22747 (11)0.0331 (6)
C170.3486 (4)0.24784 (19)0.35626 (9)0.0182 (4)
O10.5965 (3)0.22805 (14)0.36182 (7)0.0282 (4)
N210.1514 (4)0.19607 (16)0.39034 (8)0.0183 (4)
C210.1969 (4)0.11043 (18)0.43713 (9)0.0182 (5)
C220.0365 (5)0.1129 (2)0.49195 (10)0.0215 (5)
C230.0673 (5)0.0297 (2)0.53731 (10)0.0245 (5)
C240.2577 (5)0.0565 (2)0.52849 (9)0.0212 (5)
O240.2684 (3)0.13507 (14)0.57646 (7)0.0285 (4)
C2410.4823 (5)0.2180 (2)0.57344 (11)0.0314 (6)
C250.4176 (5)0.0590 (2)0.47362 (10)0.0225 (5)
C260.3853 (4)0.02478 (19)0.42806 (10)0.0218 (5)
H140.02000.41380.37220.027*
H150.16380.55430.30110.035*
H160.00700.55320.19860.043*
H210.02020.21660.38330.022*
H220.09390.17170.49810.028*
H230.04210.03140.57470.032*
H24A0.46530.26100.53390.041*
H24B0.46600.26940.60970.041*
H12C0.66220.18050.57470.041*
H250.54820.11770.46740.029*
H260.49340.02300.39050.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0356 (11)0.0325 (12)0.0241 (10)0.0033 (11)0.0013 (9)0.0069 (9)
C120.0179 (11)0.0260 (14)0.0242 (11)0.0046 (10)0.0031 (10)0.0039 (10)
Cl10.0300 (3)0.0373 (4)0.0316 (3)0.0010 (3)0.0104 (2)0.0087 (3)
C130.0130 (9)0.0202 (13)0.0197 (10)0.0033 (9)0.0041 (9)0.0016 (9)
C140.0181 (10)0.0221 (13)0.0223 (10)0.0025 (10)0.0004 (9)0.0023 (9)
C150.0256 (12)0.0189 (12)0.0357 (13)0.0024 (11)0.0031 (12)0.0023 (10)
C160.0372 (15)0.0283 (15)0.0337 (13)0.0024 (13)0.0053 (12)0.0109 (10)
C170.0166 (10)0.0173 (11)0.0206 (9)0.0010 (10)0.0021 (8)0.0040 (9)
O10.0124 (7)0.0343 (10)0.0378 (8)0.0011 (8)0.0020 (7)0.0081 (8)
N210.0112 (8)0.0225 (11)0.0211 (9)0.0035 (8)0.0011 (7)0.0023 (8)
C210.0173 (11)0.0187 (13)0.0185 (11)0.0018 (9)0.0027 (9)0.0009 (9)
C220.0188 (11)0.0209 (13)0.0247 (10)0.0025 (10)0.0008 (9)0.0013 (9)
C230.0259 (12)0.0280 (14)0.0195 (10)0.0019 (11)0.0046 (10)0.0029 (9)
C240.0249 (11)0.0206 (13)0.0182 (10)0.0011 (11)0.0029 (9)0.0010 (9)
O240.0347 (9)0.0268 (10)0.0242 (8)0.0050 (9)0.0021 (8)0.0074 (7)
C2410.0329 (13)0.0312 (15)0.0300 (12)0.0041 (12)0.0035 (11)0.0074 (11)
C250.0184 (11)0.0216 (13)0.0274 (11)0.0076 (11)0.0007 (10)0.0006 (9)
C260.0196 (11)0.0265 (13)0.0192 (10)0.0031 (10)0.0035 (9)0.0002 (9)
Geometric parameters (Å, º) top
N11—C121.319 (3)C21—C261.379 (3)
N11—C161.344 (3)C21—C221.393 (3)
C12—C131.406 (3)C22—C231.381 (3)
C12—Cl11.740 (2)C22—H220.95
C13—C141.393 (3)C23—C241.389 (3)
C13—C171.499 (3)C23—H230.95
C14—C151.384 (3)C24—O241.375 (3)
C14—H140.95C24—C251.393 (3)
C15—C161.376 (3)O24—C2411.431 (3)
C15—H150.95C241—H24A0.98
C16—H160.95C241—H24B0.98
C17—O11.231 (2)C241—H12C0.98
C17—N211.344 (3)C25—C261.389 (3)
N21—C211.431 (3)C25—H250.95
N21—H210.88C26—H260.95
C12—N11—C16117.07 (19)C22—C21—N21117.99 (18)
N11—C12—C13124.9 (2)C23—C22—C21119.9 (2)
N11—C12—Cl1114.61 (17)C23—C22—H22120.1
C13—C12—Cl1120.50 (18)C21—C22—H22120.1
C14—C13—C12116.1 (2)C22—C23—C24120.3 (2)
C14—C13—C17120.95 (18)C22—C23—H23119.9
C12—C13—C17122.9 (2)C24—C23—H23119.9
C15—C14—C13120.1 (2)O24—C24—C23115.13 (19)
C15—C14—H14120.0O24—C24—C25125.1 (2)
C13—C14—H14120.0C23—C24—C25119.8 (2)
C16—C15—C14118.3 (2)C24—O24—C241117.39 (17)
C16—C15—H15120.8O24—C241—H24A109.5
C14—C15—H15120.8O24—C241—H24B109.5
N11—C16—C15123.6 (2)H24A—C241—H24B109.5
N11—C16—H16118.2O24—C241—H12C109.5
C15—C16—H16118.2H24A—C241—H12C109.5
O1—C17—N21123.9 (2)H24B—C241—H12C109.5
O1—C17—C13121.64 (19)C26—C25—C24119.7 (2)
N21—C17—C13114.43 (17)C26—C25—H25120.2
C17—N21—C21125.51 (17)C24—C25—H25120.2
C17—N21—H21117.2C21—C26—C25120.30 (19)
C21—N21—H21117.2C21—C26—H26119.9
C26—C21—C22120.1 (2)C25—C26—H26119.9
C26—C21—N21121.89 (17)
C16—N11—C12—C130.0 (3)C13—C17—N21—C21179.40 (17)
C16—N11—C12—Cl1178.26 (19)C17—N21—C21—C2641.5 (3)
N11—C12—C13—C140.4 (3)C17—N21—C21—C22141.0 (2)
Cl1—C12—C13—C14177.73 (16)C26—C21—C22—C230.3 (3)
N11—C12—C13—C17178.3 (2)N21—C21—C22—C23177.8 (2)
Cl1—C12—C13—C173.6 (3)C21—C22—C23—C240.0 (3)
C12—C13—C14—C151.0 (3)C22—C23—C24—O24179.4 (2)
C17—C13—C14—C15177.7 (2)C22—C23—C24—C250.1 (3)
C13—C14—C15—C161.2 (3)C23—C24—O24—C241172.87 (19)
C12—N11—C16—C150.1 (4)C25—C24—O24—C2417.9 (3)
C14—C15—C16—N110.8 (4)O24—C24—C25—C26179.2 (2)
C14—C13—C17—O1131.8 (2)C23—C24—C25—C260.1 (3)
C12—C13—C17—O146.8 (3)C22—C21—C26—C250.5 (3)
C14—C13—C17—N2146.9 (3)N21—C21—C26—C25177.90 (19)
C12—C13—C17—N21134.5 (2)C24—C25—C26—C210.4 (3)
O1—C17—N21—C210.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···O1i0.881.922.785 (2)168
Symmetry code: (i) x1, y, z.
(VIII) N-(4-Cyanophenyl)-2-chloronicotinamide top
Crystal data top
C13H8ClN3OZ = 4
Mr = 257.67F(000) = 528
Triclinic, P1Dx = 1.461 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2885 (3) ÅCell parameters from 5365 reflections
b = 7.7607 (3) Åθ = 2.9–27.6°
c = 20.8849 (9) ŵ = 0.32 mm1
α = 96.456 (2)°T = 120 K
β = 92.913 (2)°Block, colourless
γ = 91.810 (2)°0.40 × 0.10 × 0.10 mm
V = 1171.49 (8) Å3
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
5365 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode3760 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
Detector resolution: 9.091 pixels mm-1θmax = 27.6°, θmin = 2.9°
ϕ & ω scansh = 99
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
k = 1010
Tmin = 0.899, Tmax = 0.969l = 2726
21639 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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0844P)2 + 1.0407P]
where P = (Fo2 + 2Fc2)/3
5365 reflections(Δ/σ)max < 0.001
325 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C13H8ClN3Oγ = 91.810 (2)°
Mr = 257.67V = 1171.49 (8) Å3
Triclinic, P1Z = 4
a = 7.2885 (3) ÅMo Kα radiation
b = 7.7607 (3) ŵ = 0.32 mm1
c = 20.8849 (9) ÅT = 120 K
α = 96.456 (2)°0.40 × 0.10 × 0.10 mm
β = 92.913 (2)°
Data collection top
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
5365 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
3760 reflections with I > 2σ(I)
Tmin = 0.899, Tmax = 0.969Rint = 0.060
21639 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.171H-atom parameters constrained
S = 1.07Δρmax = 0.74 e Å3
5365 reflectionsΔρmin = 0.35 e Å3
325 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.4024 (3)0.5334 (3)0.41399 (12)0.0257 (6)
C120.5406 (4)0.4277 (4)0.40989 (14)0.0225 (6)
Cl110.74241 (10)0.51557 (10)0.38256 (4)0.0285 (2)
C130.5387 (4)0.2603 (4)0.42747 (14)0.0206 (6)
C140.3775 (4)0.2012 (4)0.45139 (15)0.0241 (7)
C150.2276 (4)0.3077 (4)0.45524 (15)0.0268 (7)
C160.2475 (4)0.4714 (4)0.43607 (15)0.0279 (7)
C170.7039 (4)0.1471 (4)0.42314 (14)0.0211 (6)
O110.7924 (3)0.1170 (3)0.47166 (10)0.0273 (5)
N210.7375 (3)0.0842 (3)0.36189 (12)0.0235 (6)
C210.8926 (4)0.0042 (4)0.33945 (14)0.0209 (6)
C220.9149 (4)0.0138 (4)0.27334 (15)0.0232 (6)
C231.0691 (4)0.0867 (4)0.24724 (15)0.0244 (7)
C241.2018 (4)0.1517 (4)0.28771 (15)0.0221 (6)
C2411.3665 (4)0.2196 (4)0.26069 (15)0.0263 (7)
N241.4970 (4)0.2700 (4)0.23738 (14)0.0340 (7)
C251.1762 (4)0.1476 (4)0.35319 (15)0.0224 (6)
C261.0208 (4)0.0761 (4)0.37956 (15)0.0221 (6)
N310.5598 (3)1.0705 (3)0.08089 (12)0.0251 (6)
C320.4236 (4)0.9650 (4)0.08737 (14)0.0203 (6)
Cl310.21001 (10)1.06368 (10)0.11310 (4)0.0268 (2)
C330.4379 (4)0.7849 (4)0.07404 (14)0.0194 (6)
C340.6107 (4)0.7128 (4)0.05231 (15)0.0244 (7)
C350.7567 (4)0.8212 (4)0.04530 (15)0.0266 (7)
C360.7249 (4)0.9975 (4)0.05984 (15)0.0279 (7)
C370.2739 (4)0.6719 (4)0.07828 (14)0.0193 (6)
O310.1832 (3)0.6369 (3)0.03110 (10)0.0257 (5)
N410.2429 (3)0.6166 (3)0.13691 (12)0.0221 (5)
C410.0939 (4)0.5220 (4)0.15886 (14)0.0192 (6)
C420.0933 (4)0.4872 (4)0.22279 (15)0.0238 (7)
C430.0521 (4)0.4041 (4)0.24920 (15)0.0246 (7)
C440.1995 (4)0.3559 (4)0.21195 (15)0.0220 (6)
C4410.3543 (4)0.2754 (4)0.23969 (15)0.0259 (7)
N440.4780 (4)0.2120 (4)0.26268 (14)0.0326 (6)
C450.1955 (4)0.3863 (4)0.14756 (14)0.0216 (6)
C460.0501 (4)0.4687 (4)0.12041 (14)0.0217 (6)
H140.36930.08870.46510.029*
H150.11480.26890.47060.032*
H160.14530.54430.43870.034*
H210.65170.10050.33220.028*
H220.82370.02990.24600.028*
H231.08450.09240.20220.029*
H251.26590.19420.38030.027*
H261.00210.07610.42420.027*
H340.62840.59080.04240.029*
H350.87570.77480.03080.032*
H360.82481.07140.05470.033*
H410.32630.64290.16510.026*
H420.19310.52080.24830.029*
H430.05160.37980.29280.030*
H450.29400.35000.12180.026*
H460.04810.48870.07630.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0217 (13)0.0263 (14)0.0300 (15)0.0095 (11)0.0027 (11)0.0032 (11)
C120.0200 (14)0.0251 (16)0.0229 (15)0.0055 (12)0.0028 (11)0.0029 (12)
Cl110.0228 (4)0.0318 (4)0.0330 (4)0.0026 (3)0.0089 (3)0.0083 (3)
C130.0190 (14)0.0238 (16)0.0195 (14)0.0059 (12)0.0024 (11)0.0023 (11)
C140.0186 (15)0.0261 (17)0.0285 (17)0.0043 (12)0.0035 (12)0.0050 (12)
C150.0141 (14)0.0328 (18)0.0330 (18)0.0029 (13)0.0042 (12)0.0004 (13)
C160.0158 (14)0.0325 (19)0.0346 (18)0.0099 (13)0.0020 (12)0.0030 (14)
C170.0184 (14)0.0222 (16)0.0236 (15)0.0023 (12)0.0025 (12)0.0052 (12)
O110.0214 (11)0.0361 (13)0.0254 (12)0.0096 (9)0.0015 (9)0.0056 (9)
N210.0163 (12)0.0305 (15)0.0241 (13)0.0098 (11)0.0003 (10)0.0029 (11)
C210.0162 (14)0.0172 (15)0.0292 (16)0.0039 (11)0.0021 (11)0.0016 (12)
C220.0211 (15)0.0232 (16)0.0255 (16)0.0065 (12)0.0008 (12)0.0026 (12)
C230.0232 (15)0.0248 (17)0.0255 (16)0.0029 (13)0.0038 (12)0.0019 (12)
C240.0151 (14)0.0181 (15)0.0329 (17)0.0031 (11)0.0031 (12)0.0008 (12)
C2410.0218 (16)0.0243 (17)0.0323 (17)0.0034 (13)0.0009 (13)0.0006 (13)
N240.0247 (15)0.0377 (17)0.0402 (17)0.0097 (13)0.0083 (12)0.0017 (13)
C250.0172 (14)0.0184 (15)0.0319 (17)0.0071 (11)0.0006 (12)0.0035 (12)
C260.0220 (15)0.0202 (15)0.0251 (16)0.0057 (12)0.0038 (12)0.0041 (12)
N310.0202 (13)0.0281 (14)0.0280 (14)0.0104 (11)0.0032 (10)0.0043 (11)
C320.0133 (13)0.0264 (16)0.0214 (15)0.0034 (12)0.0010 (11)0.0024 (11)
Cl310.0208 (4)0.0279 (4)0.0309 (4)0.0004 (3)0.0033 (3)0.0022 (3)
C330.0174 (14)0.0218 (15)0.0200 (14)0.0028 (11)0.0035 (11)0.0048 (11)
C340.0186 (15)0.0247 (16)0.0308 (17)0.0024 (12)0.0020 (12)0.0064 (13)
C350.0146 (14)0.0347 (19)0.0317 (17)0.0001 (13)0.0009 (12)0.0097 (14)
C360.0211 (15)0.0350 (19)0.0300 (17)0.0137 (14)0.0043 (13)0.0096 (14)
C370.0163 (14)0.0174 (15)0.0241 (15)0.0001 (11)0.0017 (11)0.0010 (11)
O310.0221 (11)0.0313 (13)0.0247 (11)0.0085 (9)0.0052 (9)0.0040 (9)
N410.0165 (12)0.0280 (14)0.0233 (13)0.0093 (10)0.0048 (10)0.0060 (10)
C410.0129 (13)0.0176 (15)0.0275 (16)0.0041 (11)0.0013 (11)0.0029 (11)
C420.0223 (15)0.0242 (16)0.0262 (16)0.0086 (13)0.0071 (12)0.0043 (12)
C430.0233 (15)0.0279 (17)0.0237 (16)0.0070 (13)0.0020 (12)0.0059 (12)
C440.0191 (14)0.0155 (15)0.0311 (17)0.0032 (11)0.0015 (12)0.0020 (12)
C4410.0257 (16)0.0233 (16)0.0290 (17)0.0034 (13)0.0008 (13)0.0043 (13)
N440.0280 (15)0.0330 (16)0.0376 (16)0.0111 (12)0.0030 (12)0.0074 (12)
C450.0166 (14)0.0187 (15)0.0296 (16)0.0046 (11)0.0030 (12)0.0015 (12)
C460.0203 (15)0.0216 (15)0.0242 (15)0.0062 (12)0.0034 (12)0.0049 (12)
Geometric parameters (Å, º) top
N11—C121.319 (4)N31—C321.318 (4)
N11—C161.336 (4)N31—C361.345 (4)
C12—C131.389 (4)C32—C331.394 (4)
C12—Cl111.751 (3)C32—Cl311.745 (3)
C13—C141.385 (4)C33—C341.395 (4)
C13—C171.513 (4)C33—C371.510 (4)
C14—C151.391 (4)C34—C351.389 (4)
C14—H140.95C34—H340.95
C15—C161.380 (5)C35—C361.377 (5)
C15—H150.95C35—H350.95
C16—H160.95C36—H360.95
C17—O111.222 (3)C37—O311.224 (3)
C17—N211.354 (4)C37—N411.353 (4)
N21—C211.414 (4)N41—C411.415 (4)
N21—H210.88N41—H410.88
C21—C221.392 (4)C41—C421.391 (4)
C21—C261.395 (4)C41—C461.399 (4)
C22—C231.383 (4)C42—C431.381 (4)
C22—H220.95C42—H420.95
C23—C241.396 (4)C43—C441.395 (4)
C23—H230.95C43—H430.95
C24—C251.387 (4)C44—C451.390 (4)
C24—C2411.442 (4)C44—C4411.434 (4)
C241—N241.150 (4)C441—N441.150 (4)
C25—C261.389 (4)C45—C461.385 (4)
C25—H250.95C45—H450.95
C26—H260.95C46—H460.95
C12—N11—C16116.5 (3)C32—N31—C36117.0 (3)
N11—C12—C13125.5 (3)N31—C32—C33125.0 (3)
N11—C12—Cl11115.0 (2)N31—C32—Cl31116.0 (2)
C13—C12—Cl11119.4 (2)C33—C32—Cl31118.9 (2)
C14—C13—C12116.6 (3)C32—C33—C34116.7 (3)
C14—C13—C17120.5 (3)C32—C33—C37122.5 (3)
C12—C13—C17122.9 (3)C34—C33—C37120.7 (3)
C13—C14—C15119.6 (3)C35—C34—C33119.4 (3)
C13—C14—H14120.2C35—C34—H34120.3
C15—C14—H14120.2C33—C34—H34120.3
C16—C15—C14118.0 (3)C36—C35—C34118.5 (3)
C16—C15—H15121.0C36—C35—H35120.8
C14—C15—H15121.0C34—C35—H35120.8
N11—C16—C15123.8 (3)N31—C36—C35123.4 (3)
N11—C16—H16118.1N31—C36—H36118.3
C15—C16—H16118.1C35—C36—H36118.3
O11—C17—N21125.5 (3)O31—C37—N41125.9 (3)
O11—C17—C13121.1 (3)O31—C37—C33120.3 (3)
N21—C17—C13113.4 (2)N41—C37—C33113.9 (2)
C17—N21—C21128.4 (2)C37—N41—C41128.5 (2)
C17—N21—H21115.8C37—N41—H41115.8
C21—N21—H21115.8C41—N41—H41115.8
C22—C21—C26120.3 (3)C42—C41—C46120.2 (3)
C22—C21—N21116.0 (3)C42—C41—N41116.4 (2)
C26—C21—N21123.8 (3)C46—C41—N41123.3 (3)
C23—C22—C21120.4 (3)C43—C42—C41120.2 (3)
C23—C22—H22119.8C43—C42—H42119.9
C21—C22—H22119.8C41—C42—H42119.9
C22—C23—C24119.4 (3)C42—C43—C44120.0 (3)
C22—C23—H23120.3C42—C43—H43120.0
C24—C23—H23120.3C44—C43—H43120.0
C25—C24—C23120.1 (3)C45—C44—C43119.5 (3)
C25—C24—C241120.7 (3)C45—C44—C441120.1 (3)
C23—C24—C241119.1 (3)C43—C44—C441120.4 (3)
N24—C241—C24177.5 (3)N44—C441—C44179.1 (4)
C24—C25—C26120.7 (3)C46—C45—C44121.0 (3)
C24—C25—H25119.6C46—C45—H45119.5
C26—C25—H25119.6C44—C45—H45119.5
C25—C26—C21119.0 (3)C45—C46—C41119.0 (3)
C25—C26—H26120.5C45—C46—H46120.5
C21—C26—H26120.5C41—C46—H46120.5
C16—N11—C12—C131.1 (5)C36—N31—C32—C330.1 (4)
C16—N11—C12—Cl11178.6 (2)C36—N31—C32—Cl31178.7 (2)
N11—C12—C13—C140.2 (5)N31—C32—C33—C340.1 (4)
Cl11—C12—C13—C14177.2 (2)Cl31—C32—C33—C34178.6 (2)
N11—C12—C13—C17178.4 (3)N31—C32—C33—C37175.9 (3)
Cl11—C12—C13—C171.0 (4)Cl31—C32—C33—C372.7 (4)
C12—C13—C14—C151.4 (4)C32—C33—C34—C350.1 (4)
C17—C13—C14—C15179.7 (3)C37—C33—C34—C35176.2 (3)
C13—C14—C15—C161.4 (5)C33—C34—C35—C360.4 (4)
C12—N11—C16—C151.1 (5)C32—N31—C36—C350.2 (4)
C14—C15—C16—N110.1 (5)C34—C35—C36—N310.4 (5)
C14—C13—C17—O1170.9 (4)C32—C33—C37—O3189.6 (4)
C12—C13—C17—O11107.3 (3)C34—C33—C37—O3186.2 (4)
C14—C13—C17—N21108.1 (3)C32—C33—C37—N4190.9 (3)
C12—C13—C17—N2173.7 (4)C34—C33—C37—N4193.3 (3)
O11—C17—N21—C2110.7 (5)O31—C37—N41—C416.3 (5)
C13—C17—N21—C21170.3 (3)C33—C37—N41—C41174.2 (3)
C17—N21—C21—C22163.6 (3)C37—N41—C41—C42177.8 (3)
C17—N21—C21—C2615.1 (5)C37—N41—C41—C460.3 (5)
C26—C21—C22—C233.4 (4)C46—C41—C42—C431.8 (5)
N21—C21—C22—C23175.4 (3)N41—C41—C42—C43176.4 (3)
C21—C22—C23—C240.4 (4)C41—C42—C43—C440.5 (5)
C22—C23—C24—C251.9 (4)C42—C43—C44—C452.4 (5)
C22—C23—C24—C241177.0 (3)C42—C43—C44—C441177.6 (3)
C23—C24—C25—C261.3 (4)C43—C44—C45—C462.1 (4)
C241—C24—C25—C26177.5 (3)C441—C44—C45—C46178.0 (3)
C24—C25—C26—C211.6 (4)C44—C45—C46—C410.2 (4)
C22—C21—C26—C253.9 (4)C42—C41—C46—C452.1 (4)
N21—C21—C26—C25174.7 (3)N41—C41—C46—C45175.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N440.882.153.006 (4)164
N41—H41···N24i0.882.102.978 (4)173
C14—H14···O11ii0.952.493.334 (4)148
C15—H15···O11iii0.952.603.507 (4)160
C25—H25···N11iv0.952.523.348 (4)146
C34—H34···O31v0.952.533.327 (4)142
C35—H35···O31iii0.952.453.366 (4)161
C45—H45···N31iv0.952.533.300 (4)138
Symmetry codes: (i) x2, y+1, z; (ii) x+1, y, z+1; (iii) x1, y, z; (iv) x+1, y1, z; (v) x1, y+1, z.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC12H9ClN2OC13H11ClN2OC12H8ClFN2O·H2OC12H8Cl2N2O
Mr232.66246.69268.67267.10
Crystal system, space groupOrthorhombic, PccnTriclinic, P1Triclinic, P1Monoclinic, P21
Temperature (K)120120120120
a, b, c (Å)13.2296 (6), 21.0744 (10), 7.6898 (16)9.6824 (6), 11.3082 (7), 11.5139 (7)6.8033 (4), 8.1303 (3), 11.5356 (6)5.0855 (8), 28.982 (8), 15.607 (4)
α, β, γ (°)90, 90, 9077.453 (2), 73.445 (2), 87.978 (2)84.032 (3), 84.297 (2), 69.569 (3)90, 90.37 (2), 90
V3)2144.0 (5)1179.07 (13)593.32 (5)2300.2 (9)
Z8428
Radiation typeMo KαSynchrotron, λ = 0.67510 ÅMo KαMo Kα
µ (mm1)0.330.310.330.55
Crystal size (mm)0.24 × 0.09 × 0.020.10 × 0.02 × 0.020.18 × 0.16 × 0.030.28 × 0.07 × 0.03
Data collection
DiffractometerBruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
Bruker SMART APEX2 CCD
diffractometer
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
Bruker SADABS (Bruker, 2004)
Multi-scan
SADABS 2.10 (Sheldrick,. 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.943, 0.9930.970, 0.9940.933, 0.9900.862, 0.984
No. of measured, independent and
observed reflections
17837, 2446, 1724 [I > 2σ(I)]12982, 6881, 5217 [( > 2σ(I)]12303, 2720, 1943 [I > 2σ(I)]24726, 9787, 6370 [I > 2σ(I)]
Rint0.1040.0220.0520.053
(sin θ/λ)max1)0.6500.7140.6550.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.129, 1.07 0.044, 0.124, 1.02 0.044, 0.113, 1.05 0.069, 0.169, 1.04
No. of reflections2446688127209787
No. of parameters145309163254
No. of restraints0001
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.280.43, 0.300.26, 0.290.79, 0.54
Absolute structure???Flack (1983), 4396 Friedel pairs
Absolute structure parameter???0.54 (11)


(V)(VI)(VII)(VIII)
Crystal data
Chemical formulaC12H8BrClN2OC12H8ClIN2OC13H11ClN2O2C13H8ClN3O
Mr311.56358.55262.69257.67
Crystal system, space groupOrthorhombic, P212121Orthorhombic, PbcaOrthorhombic, P212121Triclinic, P1
Temperature (K)120120120120
a, b, c (Å)4.8810 (2), 13.3448 (2), 18.3974 (3)10.6597 (2), 25.9833 (3), 9.2044 (6)4.8536 (2), 11.8437 (4), 21.0612 (7)7.2885 (3), 7.7607 (3), 20.8849 (9)
α, β, γ (°)90, 90, 9090, 90, 9090, 90, 9096.456 (2), 92.913 (2), 91.810 (2)
V3)1198.33 (6)2549.38 (18)1210.69 (6)1171.49 (8)
Z4844
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)3.642.710.310.32
Crystal size (mm)0.16 × 0.16 × 0.160.33 × 0.18 × 0.070.34 × 0.22 × 0.120.40 × 0.10 × 0.10
Data collection
DiffractometerBruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
Bruker-Nonius 95mm CCD camera on κ goniostat
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.558, 0.5580.469, 0.8330.921, 0.9640.899, 0.969
No. of measured, independent and
observed reflections
36201, 2736, 2597 [I > 2σ(I)]19649, 2909, 2314 [I > 2σ(I)]7884, 2661, 2184 [I > 2σ(I)]21639, 5365, 3760 [I > 2σ(I)]
Rint0.0470.0380.0400.060
(sin θ/λ)max1)0.6500.6490.6490.653
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.060, 1.07 0.023, 0.056, 1.04 0.042, 0.104, 1.04 0.059, 0.171, 1.07
No. of reflections2736290926615365
No. of parameters154154164325
No. of restraints0000
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.520.39, 0.780.24, 0.350.74, 0.35
Absolute structureFlack (1983), 1098 Friedel pairs?Flack (1983), 1013 Friedel pairs?
Absolute structure parameter0.031 (7)?0.05 (7)?

Computer programs: COLLECT (Hooft, 1999), Bruker APEX2 (Bruker, 2004), DENZO (Otwinowski & Minor, 1997) & COLLECT, SAINT (Bruker, 2004), DENZO & COLLECT, SAINT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

 

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