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The asymmetric unit of the title compound, C19H22ClNO, contains two independent mol­ecules with different conformations of the isobutyl group. The benzene rings in the two mol­ecules make dihedral angles of 71.7 (1) and 76.6 (1)°. Inter­molecular N—H...O hydrogen bonds link the mol­ecules into infinite chains along [100].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034921/cv2112sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034921/cv2112Isup2.hkl
Contains datablock I

CCDC reference: 624188

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.091
  • wR factor = 0.256
  • Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.256 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.127 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT084_ALERT_2_C High R2 Value .................................. 0.26 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.22 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.07 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.61 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C217 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N-(3-Chlorophenyl)-2-(4-isobutylphenyl)propanamide top
Crystal data top
C19H22ClNOF(000) = 1344
Mr = 315.83Dx = 1.218 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4258 reflections
a = 9.8140 (16) Åθ = 2.3–23.6°
b = 32.640 (5) ŵ = 0.22 mm1
c = 10.7522 (18) ÅT = 120 K
β = 91.276 (4)°Prism, colourless
V = 3443.3 (10) Å30.42 × 0.39 × 0.28 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
7885 independent reflections
Radiation source: sealed tube4890 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.127
φ and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1212
Tmin = 0.922, Tmax = 0.943k = 4240
32978 measured reflectionsl = 1313
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)] = 0.091Hydrogen site location: difference Fourier map
wR(F2) = 0.256H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1172P)2 + 1.5681P]
where P = (Fo2 + 2Fc2)/3
7885 reflections(Δ/σ)max < 0.001
397 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 0.74 e Å3
Special details top

Experimental. IR (KBr) cm-1: 3251, 1667, 1610. 1H NMR (CDCl3) δ: 93 (6H, d, (CH3)2CH, J=6.6 Hz), 1.58 (3H, d, (ArCHCH3, J=7.2 Hz), 1.84–1.90 (1H, p, (ArCH3CH, J=6.9 Hz), 2.49 (2H, d, (CH3)2CHCH2Ar, J=7.2 Hz), 3.66–3.73 (1H, q, (CH3)2CH, J=6.9 Hz), 7.1–7.29 (5H, m, arom.), 7.74 (1H, s, arom.), 7.6 1H, s, arom.), 7.8 (2H, s, broad, NH). EIMS m/e: 295, 126, 119, 91, 64.9. Anal. Calcd. for C20H25NO C, 81.31; H, 8.53; N, 4.74; found C, 81.51; H, 8.47; N, 4.70

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.51744 (12)0.68426 (4)0.17248 (10)0.0426 (3)
O10.5965 (3)0.66863 (9)0.2863 (3)0.0324 (7)
N10.8137 (3)0.67556 (9)0.2246 (3)0.0228 (7)
H1A0.89970.67140.24610.027*
C1010.7880 (4)0.69269 (11)0.1068 (3)0.0211 (8)
C1020.6742 (4)0.68176 (11)0.0345 (3)0.0245 (8)
H10A0.60900.66300.06510.029*
C1030.6581 (4)0.69870 (12)0.0821 (4)0.0271 (9)
C1040.7493 (5)0.72636 (12)0.1293 (4)0.0342 (10)
H10B0.73460.73820.20920.041*
C1050.8635 (4)0.73657 (12)0.0569 (4)0.0328 (10)
H10C0.92910.75500.08830.039*
C1060.8819 (4)0.72003 (12)0.0599 (4)0.0281 (9)
H10H0.95980.72740.10900.034*
C1070.7193 (4)0.66477 (11)0.3086 (3)0.0226 (8)
C1080.7745 (4)0.64795 (12)0.4300 (3)0.0262 (8)
H10G0.87190.65670.43910.031*
C1090.6970 (4)0.66582 (13)0.5391 (4)0.0323 (9)
H10D0.70270.69580.53700.048*
H10E0.73740.65570.61750.048*
H10F0.60130.65740.53290.048*
C1100.7714 (4)0.60152 (12)0.4263 (3)0.0255 (8)
C1110.8892 (4)0.57917 (13)0.4105 (4)0.0318 (9)
H11A0.97340.59310.40110.038*
C1120.8862 (4)0.53704 (13)0.4084 (4)0.0346 (10)
H11B0.96880.52250.39690.041*
C1130.7663 (4)0.51508 (12)0.4224 (4)0.0296 (9)
C1140.6474 (4)0.53827 (13)0.4360 (4)0.0339 (10)
H11C0.56270.52460.44470.041*
C1150.6501 (4)0.58013 (12)0.4370 (4)0.0309 (9)
H11D0.56740.59490.44530.037*
C1160.7635 (5)0.46933 (13)0.4217 (4)0.0392 (10)
H11E0.72260.45980.49990.047*
H11F0.85850.45910.42090.047*
C1170.6851 (5)0.45053 (13)0.3132 (5)0.0426 (11)
H11G0.58980.46130.31510.051*
C1180.6780 (6)0.40378 (14)0.3256 (6)0.0610 (15)
H11H0.62730.39240.25410.092*
H11I0.63170.39660.40240.092*
H11J0.77050.39250.32820.092*
C1190.7429 (7)0.46219 (16)0.1903 (5)0.0674 (17)
H11K0.74570.49210.18320.101*
H11L0.68550.45090.12290.101*
H11M0.83550.45120.18440.101*
Cl20.03076 (12)0.68778 (4)0.71905 (10)0.0420 (3)
O20.0979 (3)0.66789 (9)0.2629 (2)0.0319 (7)
N20.3169 (3)0.67405 (9)0.3301 (3)0.0233 (7)
H2A0.40230.66880.31240.028*
C2010.2918 (4)0.69408 (11)0.4444 (3)0.0219 (8)
C2020.1824 (4)0.68323 (11)0.5160 (3)0.0243 (8)
H20A0.11970.66280.48820.029*
C2030.1663 (4)0.70243 (12)0.6278 (3)0.0272 (9)
C2040.2535 (4)0.73258 (12)0.6707 (4)0.0324 (9)
H20B0.23840.74600.74760.039*
C2050.3631 (4)0.74280 (12)0.5994 (4)0.0326 (9)
H20C0.42570.76310.62820.039*
C2060.3831 (4)0.72382 (11)0.4856 (4)0.0269 (8)
H20H0.45860.73110.43650.032*
C2070.2204 (4)0.66249 (11)0.2466 (3)0.0226 (8)
C2080.2722 (4)0.64094 (12)0.1316 (4)0.0271 (9)
H20G0.37120.64750.12380.033*
C2090.1976 (4)0.65616 (13)0.0147 (4)0.0357 (10)
H20D0.23280.64190.05820.054*
H20E0.21210.68570.00580.054*
H20F0.09990.65060.02130.054*
C2100.2587 (4)0.59510 (12)0.1515 (3)0.0279 (9)
C2110.3716 (4)0.57134 (14)0.1811 (4)0.0393 (11)
H21A0.45880.58390.18720.047*
C2120.3605 (5)0.52975 (14)0.2021 (4)0.0426 (11)
H21B0.43990.51420.22220.051*
C2130.2345 (5)0.51032 (13)0.1941 (4)0.0360 (10)
C2140.1226 (4)0.53383 (13)0.1631 (4)0.0372 (10)
H21C0.03570.52110.15550.045*
C2150.1336 (4)0.57533 (13)0.1428 (4)0.0358 (10)
H21D0.05400.59070.12240.043*
C2160.2182 (6)0.46505 (14)0.2177 (4)0.0468 (12)
H21E0.14350.46110.27700.056*
H21F0.30310.45470.25800.056*
C2170.1876 (5)0.43945 (13)0.1023 (4)0.0407 (11)
H21G0.11020.45270.05550.049*
C2180.1438 (5)0.39659 (14)0.1371 (5)0.0549 (14)
H21H0.06490.39810.19110.082*
H21I0.21910.38270.18120.082*
H21J0.11930.38130.06150.082*
C2190.3091 (7)0.43800 (17)0.0174 (6)0.0671 (17)
H21K0.33640.46600.00390.101*
H21L0.28420.42300.05880.101*
H21M0.38520.42410.06010.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0376 (6)0.0546 (7)0.0352 (6)0.0080 (5)0.0113 (5)0.0044 (5)
O10.0115 (13)0.0497 (18)0.0361 (15)0.0007 (12)0.0022 (11)0.0067 (13)
N10.0117 (15)0.0291 (18)0.0275 (16)0.0006 (13)0.0005 (12)0.0003 (13)
C1010.0168 (18)0.0187 (19)0.0278 (18)0.0050 (15)0.0015 (14)0.0016 (14)
C1020.0170 (18)0.024 (2)0.033 (2)0.0011 (15)0.0012 (15)0.0039 (15)
C1030.025 (2)0.027 (2)0.0294 (19)0.0111 (17)0.0026 (16)0.0053 (16)
C1040.045 (3)0.024 (2)0.034 (2)0.0094 (19)0.0035 (19)0.0051 (17)
C1050.039 (2)0.020 (2)0.040 (2)0.0009 (18)0.0112 (19)0.0005 (17)
C1060.020 (2)0.027 (2)0.037 (2)0.0003 (16)0.0053 (16)0.0042 (17)
C1070.0138 (18)0.0219 (19)0.0320 (19)0.0013 (15)0.0020 (15)0.0014 (15)
C1080.0171 (19)0.030 (2)0.032 (2)0.0010 (16)0.0037 (15)0.0015 (16)
C1090.038 (2)0.028 (2)0.031 (2)0.0028 (19)0.0018 (18)0.0024 (17)
C1100.023 (2)0.027 (2)0.0268 (19)0.0021 (16)0.0037 (15)0.0043 (15)
C1110.022 (2)0.033 (2)0.040 (2)0.0023 (18)0.0015 (17)0.0008 (18)
C1120.025 (2)0.037 (3)0.041 (2)0.0078 (19)0.0032 (18)0.0009 (19)
C1130.033 (2)0.027 (2)0.029 (2)0.0040 (18)0.0063 (17)0.0012 (16)
C1140.026 (2)0.030 (2)0.046 (2)0.0029 (18)0.0032 (18)0.0016 (18)
C1150.022 (2)0.025 (2)0.045 (2)0.0044 (17)0.0047 (17)0.0012 (17)
C1160.048 (3)0.028 (2)0.042 (2)0.007 (2)0.004 (2)0.0058 (18)
C1170.034 (3)0.029 (2)0.064 (3)0.007 (2)0.009 (2)0.008 (2)
C1180.067 (4)0.028 (3)0.088 (4)0.002 (3)0.003 (3)0.007 (3)
C1190.120 (5)0.041 (3)0.041 (3)0.002 (3)0.016 (3)0.003 (2)
Cl20.0396 (6)0.0514 (7)0.0355 (6)0.0040 (5)0.0124 (5)0.0020 (5)
O20.0136 (13)0.0449 (18)0.0371 (15)0.0014 (12)0.0030 (11)0.0086 (13)
N20.0117 (15)0.0285 (17)0.0298 (16)0.0007 (13)0.0006 (12)0.0031 (13)
C2010.0169 (18)0.0186 (19)0.0298 (19)0.0047 (15)0.0039 (15)0.0002 (15)
C2020.0183 (19)0.023 (2)0.031 (2)0.0038 (15)0.0035 (15)0.0029 (15)
C2030.026 (2)0.028 (2)0.0277 (19)0.0104 (17)0.0011 (16)0.0052 (16)
C2040.039 (2)0.029 (2)0.028 (2)0.0111 (19)0.0076 (18)0.0055 (17)
C2050.033 (2)0.022 (2)0.042 (2)0.0004 (18)0.0144 (18)0.0021 (17)
C2060.0205 (19)0.022 (2)0.038 (2)0.0011 (16)0.0067 (16)0.0068 (16)
C2070.0136 (18)0.0196 (19)0.035 (2)0.0021 (15)0.0008 (15)0.0018 (15)
C2080.0161 (18)0.032 (2)0.033 (2)0.0044 (16)0.0044 (15)0.0061 (16)
C2090.037 (2)0.034 (2)0.035 (2)0.004 (2)0.0012 (19)0.0005 (18)
C2100.025 (2)0.031 (2)0.0269 (19)0.0023 (17)0.0021 (16)0.0056 (16)
C2110.024 (2)0.037 (3)0.056 (3)0.0004 (19)0.012 (2)0.006 (2)
C2120.038 (3)0.032 (3)0.057 (3)0.009 (2)0.020 (2)0.003 (2)
C2130.044 (3)0.032 (2)0.031 (2)0.000 (2)0.0034 (19)0.0034 (17)
C2140.032 (2)0.032 (2)0.048 (3)0.006 (2)0.0000 (19)0.0036 (19)
C2150.025 (2)0.030 (2)0.053 (3)0.0008 (18)0.0006 (19)0.0023 (19)
C2160.065 (3)0.035 (3)0.040 (2)0.004 (2)0.008 (2)0.002 (2)
C2170.039 (3)0.032 (2)0.050 (3)0.007 (2)0.010 (2)0.000 (2)
C2180.055 (3)0.027 (3)0.082 (4)0.002 (2)0.004 (3)0.007 (2)
C2190.093 (5)0.042 (3)0.067 (4)0.006 (3)0.025 (3)0.002 (3)
Geometric parameters (Å, º) top
Cl1—C1031.735 (4)Cl2—C2031.738 (4)
O1—C1071.229 (4)O2—C2071.232 (4)
N1—C1071.355 (5)N2—C2071.344 (5)
N1—C1011.402 (5)N2—C2011.419 (5)
N1—H1A0.8800N2—H2A0.8800
C101—C1061.386 (5)C201—C2021.381 (5)
C101—C1021.393 (5)C201—C2061.387 (5)
C102—C1031.377 (5)C202—C2031.367 (5)
C102—H10A0.9500C202—H20A0.9500
C103—C1041.376 (6)C203—C2041.377 (6)
C104—C1051.390 (6)C204—C2051.375 (6)
C104—H10B0.9500C204—H20B0.9500
C105—C1061.376 (6)C205—C2061.389 (6)
C105—H10C0.9500C205—H20C0.9500
C106—H10H0.9500C206—H20H0.9500
C107—C1081.506 (5)C207—C2081.520 (5)
C108—C1101.517 (5)C208—C2101.518 (5)
C108—C1091.529 (5)C208—C2091.524 (6)
C108—H10G1.0000C208—H20G1.0000
C109—H10D0.9800C209—H20D0.9800
C109—H10E0.9800C209—H20E0.9800
C109—H10F0.9800C209—H20F0.9800
C110—C1111.380 (5)C210—C2111.385 (6)
C110—C1151.387 (5)C210—C2151.388 (6)
C111—C1121.376 (6)C211—C2121.381 (6)
C111—H11A0.9500C211—H21A0.9500
C112—C1131.389 (6)C212—C2131.391 (6)
C112—H11B0.9500C212—H21B0.9500
C113—C1141.401 (6)C213—C2141.375 (6)
C113—C1161.494 (6)C213—C2161.508 (6)
C114—C1151.367 (6)C214—C2151.376 (6)
C114—H11C0.9500C214—H21C0.9500
C115—H11D0.9500C215—H21D0.9500
C116—C1171.514 (6)C216—C2171.520 (6)
C116—H11E0.9900C216—H21E0.9900
C116—H11F0.9900C216—H21F0.9900
C117—C1191.498 (7)C217—C2181.513 (6)
C117—C1181.533 (6)C217—C2191.519 (7)
C117—H11G1.0000C217—H21G1.0000
C118—H11H0.9800C218—H21H0.9800
C118—H11I0.9800C218—H21I0.9800
C118—H11J0.9800C218—H21J0.9800
C119—H11K0.9800C219—H21K0.9800
C119—H11L0.9800C219—H21L0.9800
C119—H11M0.9800C219—H21M0.9800
C107—N1—C101126.4 (3)C207—N2—C201125.1 (3)
C107—N1—H1A116.8C207—N2—H2A117.5
C101—N1—H1A116.8C201—N2—H2A117.5
C106—C101—C102119.6 (3)C202—C201—C206120.4 (3)
C106—C101—N1118.5 (3)C202—C201—N2121.1 (3)
C102—C101—N1121.8 (3)C206—C201—N2118.4 (3)
C103—C102—C101118.7 (4)C203—C202—C201118.6 (4)
C103—C102—H10A120.7C203—C202—H20A120.7
C101—C102—H10A120.7C201—C202—H20A120.7
C104—C103—C102122.4 (4)C202—C203—C204122.6 (4)
C104—C103—Cl1119.2 (3)C202—C203—Cl2118.4 (3)
C102—C103—Cl1118.4 (3)C204—C203—Cl2119.0 (3)
C103—C104—C105118.3 (4)C205—C204—C203118.3 (4)
C103—C104—H10B120.8C205—C204—H20B120.8
C105—C104—H10B120.8C203—C204—H20B120.8
C106—C105—C104120.3 (4)C204—C205—C206120.7 (4)
C106—C105—H10C119.8C204—C205—H20C119.7
C104—C105—H10C119.8C206—C205—H20C119.7
C105—C106—C101120.6 (4)C201—C206—C205119.4 (4)
C105—C106—H10H119.7C201—C206—H20H120.3
C101—C106—H10H119.7C205—C206—H20H120.3
O1—C107—N1121.7 (3)O2—C207—N2122.7 (3)
O1—C107—C108122.6 (3)O2—C207—C208121.8 (3)
N1—C107—C108115.7 (3)N2—C207—C208115.5 (3)
C107—C108—C110109.6 (3)C210—C208—C207108.0 (3)
C107—C108—C109110.5 (3)C210—C208—C209113.3 (3)
C110—C108—C109113.0 (3)C207—C208—C209110.9 (3)
C107—C108—H10G107.8C210—C208—H20G108.2
C110—C108—H10G107.8C207—C208—H20G108.1
C109—C108—H10G107.8C209—C208—H20G108.2
C108—C109—H10D109.5C208—C209—H20D109.5
C108—C109—H10E109.5C208—C209—H20E109.5
H10D—C109—H10E109.5H20D—C209—H20E109.5
C108—C109—H10F109.5C208—C209—H20F109.5
H10D—C109—H10F109.5H20D—C209—H20F109.5
H10E—C109—H10F109.5H20E—C209—H20F109.5
C111—C110—C115117.8 (4)C211—C210—C215117.2 (4)
C111—C110—C108121.0 (3)C211—C210—C208120.8 (4)
C115—C110—C108121.2 (3)C215—C210—C208121.9 (4)
C112—C111—C110120.8 (4)C212—C211—C210121.5 (4)
C112—C111—H11A119.6C212—C211—H21A119.2
C110—C111—H11A119.6C210—C211—H21A119.3
C111—C112—C113122.1 (4)C211—C212—C213120.8 (4)
C111—C112—H11B118.9C211—C212—H21B119.6
C113—C112—H11B118.9C213—C212—H21B119.6
C112—C113—C114116.3 (4)C214—C213—C212117.7 (4)
C112—C113—C116122.1 (4)C214—C213—C216120.1 (4)
C114—C113—C116121.7 (4)C212—C213—C216122.2 (4)
C115—C114—C113121.6 (4)C213—C214—C215121.5 (4)
C115—C114—H11C119.2C213—C214—H21C119.2
C113—C114—H11C119.2C215—C214—H21C119.2
C114—C115—C110121.3 (4)C214—C215—C210121.3 (4)
C114—C115—H11D119.3C214—C215—H21D119.4
C110—C115—H11D119.3C210—C215—H21D119.4
C113—C116—C117114.7 (4)C213—C216—C217114.9 (4)
C113—C116—H11E108.6C213—C216—H21E108.5
C117—C116—H11E108.6C217—C216—H21E108.5
C113—C116—H11F108.6C213—C216—H21F108.5
C117—C116—H11F108.6C217—C216—H21F108.5
H11E—C116—H11F107.6H21E—C216—H21F107.5
C119—C117—C116112.4 (4)C218—C217—C219110.5 (4)
C119—C117—C118110.4 (4)C218—C217—C216111.0 (4)
C116—C117—C118111.1 (4)C219—C217—C216111.3 (4)
C119—C117—H11G107.6C218—C217—H21G107.9
C116—C117—H11G107.6C219—C217—H21G107.9
C118—C117—H11G107.6C216—C217—H21G107.9
C117—C118—H11H109.5C217—C218—H21H109.5
C117—C118—H11I109.5C217—C218—H21I109.5
H11H—C118—H11I109.5H21H—C218—H21I109.5
C117—C118—H11J109.5C217—C218—H21J109.5
H11H—C118—H11J109.5H21H—C218—H21J109.5
H11I—C118—H11J109.5H21I—C218—H21J109.5
C117—C119—H11K109.5C217—C219—H21K109.5
C117—C119—H11L109.5C217—C219—H21L109.5
H11K—C119—H11L109.5H21K—C219—H21L109.5
C117—C119—H11M109.5C217—C219—H21M109.5
H11K—C119—H11M109.5H21K—C219—H21M109.5
H11L—C119—H11M109.5H21L—C219—H21M109.5
C107—N1—C101—C106147.6 (4)C207—N2—C201—C20239.4 (5)
C107—N1—C101—C10235.0 (5)C207—N2—C201—C206143.2 (4)
C106—C101—C102—C1030.2 (5)C206—C201—C202—C2030.1 (5)
N1—C101—C102—C103177.6 (3)N2—C201—C202—C203177.4 (3)
C101—C102—C103—C1040.8 (6)C201—C202—C203—C2041.1 (6)
C101—C102—C103—Cl1179.0 (3)C201—C202—C203—Cl2178.5 (3)
C102—C103—C104—C1051.7 (6)C202—C203—C204—C2051.9 (6)
Cl1—C103—C104—C105178.0 (3)Cl2—C203—C204—C205177.7 (3)
C103—C104—C105—C1061.6 (6)C203—C204—C205—C2061.5 (6)
C104—C105—C106—C1010.7 (6)C202—C201—C206—C2050.4 (5)
C102—C101—C106—C1050.3 (5)N2—C201—C206—C205177.8 (3)
N1—C101—C106—C105177.8 (3)C204—C205—C206—C2010.4 (6)
C101—N1—C107—O11.4 (6)C201—N2—C207—O21.0 (6)
C101—N1—C107—C108178.5 (3)C201—N2—C207—C208179.2 (3)
O1—C107—C108—C11082.6 (4)O2—C207—C208—C21080.6 (4)
N1—C107—C108—C11097.5 (4)N2—C207—C208—C21097.5 (4)
O1—C107—C108—C10942.6 (5)O2—C207—C208—C20944.1 (5)
N1—C107—C108—C109137.3 (3)N2—C207—C208—C209137.8 (3)
C107—C108—C110—C111104.3 (4)C207—C208—C210—C211103.7 (4)
C109—C108—C110—C111131.9 (4)C209—C208—C210—C211133.0 (4)
C107—C108—C110—C11574.8 (4)C207—C208—C210—C21575.3 (5)
C109—C108—C110—C11548.9 (5)C209—C208—C210—C21548.0 (5)
C115—C110—C111—C1121.4 (6)C215—C210—C211—C2120.5 (6)
C108—C110—C111—C112179.4 (4)C208—C210—C211—C212178.6 (4)
C110—C111—C112—C1130.4 (6)C210—C211—C212—C2130.1 (7)
C111—C112—C113—C1141.5 (6)C211—C212—C213—C2140.9 (7)
C111—C112—C113—C116179.2 (4)C211—C212—C213—C216179.4 (4)
C112—C113—C114—C1150.9 (6)C212—C213—C214—C2151.2 (7)
C116—C113—C114—C115179.8 (4)C216—C213—C214—C215179.0 (4)
C113—C114—C115—C1100.9 (6)C213—C214—C215—C2100.7 (7)
C111—C110—C115—C1142.0 (6)C211—C210—C215—C2140.1 (6)
C108—C110—C115—C114178.8 (4)C208—C210—C215—C214178.9 (4)
C112—C113—C116—C117114.6 (5)C214—C213—C216—C21771.8 (6)
C114—C113—C116—C11764.7 (5)C212—C213—C216—C217107.9 (5)
C113—C116—C117—C11960.3 (5)C213—C216—C217—C218168.0 (4)
C113—C116—C117—C118175.5 (4)C213—C216—C217—C21968.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.881.952.821 (4)169
N2—H2A···O10.881.932.800 (4)168
Symmetry code: (i) x+1, y, z.
 

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