Literature DB >> 22969598

N,N,N',N'-Tetra-methyl-phthalamide.

Adel Hamada, Yamina Boudinar, Adel Beghidja, Mehdi Boutebdja.   

Abstract

The title compound, C(12)H(16)N(2)O(2), crystallized from toluene with two independent mol-ecules in the asymmetric unit. The dihedral angles between the amide groups and the benzene ring are 60.87 (11) and 54.08 (11)° in one independent molecule and 60.13 (11) and 64.64 (11) in the other. The crystal structure features weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Entities:  

Year:  2012        PMID： 22969598      PMCID： PMC3435727          DOI： 10.1107/S1600536812035167

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related structures, see: Altamura et al. (2005 ▶); Anderson et al. (2004 ▶); Clayden et al. (2001 ▶); Comins et al. (1998 ▶); Sakamoto et al. (2004 ▶).

Experimental

Crystal data

C12H16N2O2 M = 220.27 Monoclinic, a = 6.7337 (6) Å b = 18.1230 (14) Å c = 9.8216 (8) Å β = 104.918 (3)° V = 1158.18 (17) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 100 K 0.56 × 0.52 × 0.33 mm

Data collection

Bruker APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.925, T max = 0.972 8205 measured reflections 2739 independent reflections 2414 reflections with I > 2σ(I) R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.124 S = 1.06 2739 reflections 297 parameters 1 restraint H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.34 e Å−3 Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ATOMS (Dowty, 1995 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035167/bq2372sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035167/bq2372Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812035167/bq2372Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C12H16N2O2F(000) = 472
Mr = 220.27Dx = 1.263 Mg m−3
Monoclinic, P21Melting point: 118 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.7337 (6) ÅCell parameters from 2761 reflections
b = 18.1230 (14) Åθ = 2.4–26.8°
c = 9.8216 (8) ŵ = 0.09 mm−1
β = 104.918 (3)°T = 100 K
V = 1158.18 (17) Å3Needles, colourless
Z = 40.56 × 0.52 × 0.33 mm
Bruker APEXII diffractometer2739 independent reflections
Graphite monochromator2414 reflections with I > 2σ(I)
Detector resolution: 18.4 pixels mm-1Rint = 0.045
CCD rotation images, thin slices scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)h = −8→8
Tmin = 0.925, Tmax = 0.972k = −23→20
8205 measured reflectionsl = −11→12
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0785P)2] where P = (Fo2 + 2Fc2)/3
2739 reflections(Δ/σ)max < 0.001
297 parametersΔρmax = 0.32 e Å−3
1 restraintΔρmin = −0.34 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.
xyzUiso*/Ueq
O10.7861 (3)0.24084 (11)−0.0065 (2)0.0216 (6)
O20.8041 (3)0.28421 (11)0.3142 (2)0.0235 (6)
N10.4493 (3)0.26282 (13)−0.0175 (2)0.0195 (7)
N21.0989 (4)0.21659 (13)0.3653 (2)0.0220 (7)
C10.6269 (4)0.22638 (15)0.0296 (3)0.0171 (7)
C20.6276 (4)0.16096 (14)0.1249 (3)0.0168 (7)
C30.5027 (4)0.10057 (15)0.0751 (3)0.0189 (7)
C40.5113 (4)0.03795 (16)0.1583 (3)0.0235 (8)
C50.6447 (4)0.03548 (15)0.2915 (3)0.0211 (8)
C60.7738 (4)0.09499 (15)0.3414 (3)0.0200 (7)
C70.7675 (4)0.15789 (14)0.2577 (3)0.0171 (7)
C80.8934 (4)0.22495 (16)0.3135 (3)0.0189 (7)
C90.4327 (5)0.32006 (16)−0.1231 (3)0.0244 (8)
C100.2644 (4)0.25242 (16)0.0331 (3)0.0232 (8)
C111.2112 (4)0.14818 (17)0.3610 (3)0.0261 (8)
C121.2221 (5)0.27854 (19)0.4338 (3)0.0312 (9)
O30.1819 (3)0.12996 (12)0.7353 (2)0.0259 (6)
O4−0.0391 (4)−0.02611 (13)0.5606 (2)0.0358 (7)
N3−0.1580 (3)0.14947 (12)0.7148 (2)0.0186 (6)
N40.2973 (4)−0.05367 (13)0.6492 (3)0.0258 (8)
C130.0169 (4)0.11065 (15)0.7583 (3)0.0188 (7)
C140.0152 (4)0.04326 (15)0.8474 (3)0.0180 (7)
C15−0.0313 (4)0.05018 (16)0.9770 (3)0.0209 (8)
C16−0.0171 (5)−0.01003 (17)1.0661 (3)0.0224 (8)
C170.0435 (4)−0.07820 (16)1.0259 (3)0.0209 (8)
C180.0923 (4)−0.08572 (14)0.8968 (3)0.0206 (7)
C190.0795 (4)−0.02558 (15)0.8073 (3)0.0189 (7)
C200.1098 (5)−0.03514 (15)0.6626 (3)0.0235 (8)
C21−0.1553 (5)0.22148 (16)0.6495 (3)0.0244 (8)
C22−0.3615 (4)0.12250 (17)0.7172 (3)0.0243 (8)
C230.3187 (7)−0.0733 (2)0.5096 (4)0.0426 (13)
C240.4731 (5)−0.06937 (18)0.7671 (3)0.0292 (9)
H30.412900.10210−0.014300.0230*
H40.42730−0.002300.124400.0280*
H50.64820−0.006000.347800.0250*
H60.864400.092900.430500.0240*
H9A0.560900.32440−0.148200.0370*
H9B0.400600.36620−0.085700.0370*
H9C0.325700.30750−0.205200.0370*
H10A0.293200.218100.110100.0350*
H10B0.155400.23350−0.042000.0350*
H10C0.223500.298900.064200.0350*
H11A1.137700.118600.283200.0390*
H11B1.224500.121500.447300.0390*
H11C1.345300.159400.349500.0390*
H12A1.135300.320800.431700.0470*
H12B1.325000.289800.385100.0470*
H12C1.287500.265900.529800.0470*
H15−0.072300.095701.004100.0250*
H16−0.04820−0.004801.152500.0270*
H170.05160−0.118801.085000.0250*
H180.13380−0.131300.870500.0250*
H21A−0.019700.231400.639600.0370*
H21B−0.193200.258700.707600.0370*
H21C−0.251200.221700.558300.0370*
H22A−0.347500.079100.774900.0360*
H22B−0.438200.110700.623000.0360*
H22C−0.432600.160000.755200.0360*
H23A0.22120−0.045800.439500.0640*
H23B0.29370−0.125100.494000.0640*
H23C0.45540−0.061800.503600.0640*
H24A0.47420−0.120900.790300.0440*
H24B0.46360−0.040500.847200.0440*
H24C0.59760−0.057100.741700.0440*
U11U22U33U12U13U23
O10.0140 (10)0.0250 (10)0.0271 (10)−0.0016 (8)0.0076 (8)0.0017 (8)
O20.0234 (11)0.0206 (9)0.0257 (10)0.0012 (9)0.0047 (9)−0.0004 (8)
N10.0116 (11)0.0236 (12)0.0242 (11)0.0015 (10)0.0063 (9)0.0041 (9)
N20.0166 (12)0.0240 (11)0.0235 (11)−0.0029 (10)0.0019 (10)−0.0011 (9)
C10.0128 (12)0.0197 (12)0.0185 (12)−0.0004 (11)0.0033 (10)−0.0047 (10)
C20.0144 (12)0.0182 (11)0.0193 (12)0.0025 (10)0.0069 (10)−0.0008 (10)
C30.0087 (12)0.0237 (12)0.0245 (13)0.0005 (11)0.0044 (10)−0.0019 (11)
C40.0134 (13)0.0222 (13)0.0365 (15)−0.0026 (11)0.0094 (12)−0.0036 (12)
C50.0181 (14)0.0188 (12)0.0290 (14)0.0027 (11)0.0106 (12)0.0048 (11)
C60.0149 (13)0.0226 (12)0.0233 (13)0.0029 (11)0.0066 (11)−0.0009 (10)
C70.0117 (12)0.0188 (12)0.0215 (12)0.0017 (11)0.0057 (10)−0.0017 (10)
C80.0178 (13)0.0228 (12)0.0169 (12)0.0005 (12)0.0058 (10)0.0026 (10)
C90.0179 (14)0.0258 (13)0.0273 (14)0.0004 (12)0.0020 (12)0.0050 (11)
C100.0127 (13)0.0242 (13)0.0338 (15)0.0013 (11)0.0082 (12)0.0014 (12)
C110.0122 (13)0.0331 (15)0.0310 (15)0.0020 (13)0.0017 (12)0.0005 (12)
C120.0271 (17)0.0319 (15)0.0297 (15)−0.0084 (15)−0.0014 (13)−0.0054 (13)
O30.0141 (10)0.0294 (10)0.0368 (11)−0.0012 (9)0.0111 (9)0.0060 (9)
O40.0446 (15)0.0339 (11)0.0247 (11)0.0143 (12)0.0015 (10)0.0000 (9)
N30.0120 (11)0.0202 (11)0.0231 (11)0.0032 (9)0.0036 (9)0.0016 (9)
N40.0330 (15)0.0220 (11)0.0273 (13)0.0061 (11)0.0165 (12)0.0022 (9)
C130.0145 (13)0.0218 (12)0.0203 (12)0.0007 (11)0.0047 (10)−0.0033 (10)
C140.0092 (12)0.0189 (12)0.0242 (13)0.0001 (10)0.0010 (10)−0.0006 (10)
C150.0127 (13)0.0236 (12)0.0265 (14)0.0004 (11)0.0052 (11)−0.0040 (11)
C160.0159 (14)0.0285 (14)0.0241 (13)−0.0028 (12)0.0076 (12)−0.0013 (11)
C170.0112 (13)0.0239 (13)0.0261 (14)−0.0042 (11)0.0020 (11)0.0025 (11)
C180.0166 (13)0.0177 (12)0.0259 (13)−0.0007 (11)0.0025 (11)−0.0029 (10)
C190.0109 (13)0.0204 (12)0.0239 (13)−0.0003 (11)0.0019 (10)−0.0011 (10)
C200.0293 (17)0.0163 (12)0.0245 (14)0.0042 (12)0.0060 (13)0.0017 (10)
C210.0225 (15)0.0248 (13)0.0277 (14)0.0064 (13)0.0098 (12)0.0050 (12)
C220.0084 (13)0.0300 (14)0.0321 (15)0.0020 (12)0.0008 (11)0.0025 (12)
C230.064 (3)0.0364 (17)0.0380 (19)0.0132 (19)0.0323 (19)0.0050 (15)
C240.0218 (16)0.0261 (14)0.0431 (17)−0.0013 (13)0.0145 (14)−0.0019 (13)
O1—C11.241 (3)C10—H10C0.9600
O2—C81.232 (4)C10—H10B0.9600
O3—C131.240 (3)C11—H11B0.9600
O4—C201.232 (4)C11—H11C0.9600
N1—C101.467 (3)C11—H11A0.9600
N1—C11.340 (4)C12—H12B0.9600
N1—C91.451 (4)C12—H12C0.9600
N2—C111.459 (4)C12—H12A0.9600
N2—C81.354 (4)C13—C141.504 (4)
N2—C121.454 (4)C14—C151.393 (4)
N3—C131.344 (3)C14—C191.410 (4)
N3—C221.461 (4)C15—C161.387 (4)
N3—C211.456 (4)C16—C171.390 (4)
N4—C231.459 (5)C17—C181.396 (4)
N4—C241.455 (4)C18—C191.389 (4)
N4—C201.345 (4)C19—C201.497 (4)
C1—C21.510 (4)C15—H150.9300
C2—C71.400 (4)C16—H160.9300
C2—C31.390 (4)C17—H170.9300
C3—C41.391 (4)C18—H180.9300
C4—C51.384 (4)C21—H21A0.9600
C5—C61.393 (4)C21—H21B0.9600
C6—C71.400 (4)C21—H21C0.9600
C7—C81.502 (4)C22—H22A0.9600
C3—H30.9300C22—H22B0.9600
C4—H40.9300C22—H22C0.9600
C5—H50.9300C23—H23A0.9600
C6—H60.9300C23—H23B0.9600
C9—H9A0.9600C23—H23C0.9600
C9—H9B0.9600C24—H24A0.9600
C9—H9C0.9600C24—H24B0.9600
C10—H10A0.9600C24—H24C0.9600
O1···O23.218 (3)C16···H4v2.9000
O1···C83.052 (3)C17···H4v2.8700
O1···C10i3.150 (3)C17···H10Cx2.8600
O1···C22ii3.400 (4)C18···H24B2.7900
O1···C18iii3.355 (3)C18···H10Cx3.0800
O2···C24iii3.224 (4)C18···H24A3.0800
O2···C12.936 (3)C19···H24B2.5300
O2···C20iii3.322 (3)C22···H153.0200
O2···N4iii3.059 (3)C24···H182.9500
O2···C23iii3.329 (4)C24···H22Ai2.9400
O2···C18iii3.329 (3)H3···C14vii2.8800
O2···O13.218 (3)H3···O3vii2.6000
O3···C203.085 (3)H3···N12.9200
O3···C22i3.128 (3)H3···C102.9800
O4···C133.111 (4)H3···C13vii3.0100
O4···C6iv3.105 (4)H4···C16vii2.9000
O4···C5iv3.141 (4)H4···C17vii2.8700
O1···H21Bii2.8700H5···O4i2.5800
O1···H22Cii2.8300H5···H23C2.4600
O1···H9A2.3300H6···C112.7800
O1···H18iii2.6600H6···H11B2.4400
O1···H10Bi2.6000H6···O4i2.5100
O1···H15ii2.7900H6···N22.9100
O2···H12A2.3300H9A···O12.3300
O2···H24Aiii2.5600H9B···H10C2.4500
O2···H18iii2.4900H9C···H10B2.5700
O2···H21Ci2.7600H10A···H11Civ2.5200
O2···H23Biii2.7100H10A···C11iv2.9500
O3···H11Biv2.9200H10A···C22.4500
O3···H21A2.3300H10A···C32.6300
O3···H3v2.6000H10B···H9C2.5700
O3···H22Ci2.6100H10B···C13vii2.9500
O4···H6iv2.5100H10B···O1iv2.6000
O4···H23A2.3800H10C···H9B2.4500
O4···H5iv2.5800H10C···C17xi2.8600
O4···H12Avi2.8500H10C···C18xi3.0800
N4···O2vi3.059 (3)H10C···H17xi2.5300
N1···H32.9200H11A···C62.6900
N2···H62.9100H11A···C72.5400
N3···H152.9200H11B···O3i2.9200
C1···O22.936 (3)H11B···C62.9800
C3···C15vii3.593 (4)H11B···H62.4400
C3···C103.159 (4)H11B···H22Bix2.4800
C4···C16vii3.546 (4)H11C···H10Ai2.5200
C5···O4i3.141 (4)H11C···H12B2.4000
C6···C113.058 (4)H12A···O22.3300
C6···O4i3.105 (4)H12A···O4iii2.8500
C8···O13.052 (3)H12B···H11C2.4000
C8···C21i3.400 (4)H15···O1viii2.7900
C10···O1iv3.150 (3)H15···N32.9200
C10···C33.159 (4)H15···C2viii2.8500
C11···C63.058 (4)H15···C223.0200
C13···O43.111 (4)H15···H22A2.5400
C15···C3v3.593 (4)H16···C4viii3.0800
C15···C223.202 (4)H16···C5viii2.8500
C16···C4v3.546 (4)H16···C6viii3.0500
C18···O1vi3.355 (3)H17···H10Cx2.5300
C18···C243.157 (4)H18···C242.9500
C18···O2vi3.329 (3)H18···O1vi2.6600
C20···O33.085 (3)H18···O2vi2.4900
C20···O2vi3.322 (3)H18···C1vi3.0700
C21···C8iv3.400 (4)H21A···O32.3300
C22···C153.202 (4)H21A···C12iv3.0300
C22···O3iv3.128 (3)H21B···O1viii2.8700
C22···O1viii3.400 (4)H21B···H22C2.5300
C23···O2vi3.329 (4)H21C···O2iv2.7600
C24···O2vi3.224 (4)H21C···C8iv2.8200
C24···C183.157 (4)H21C···H22B2.5400
C1···H22Cii2.8800H22A···C142.4500
C1···H18iii3.0700H22A···C152.5600
C2···H15ii2.8500H22A···C24iv2.9400
C2···H10A2.4500H22A···H152.5400
C3···H10A2.6300H22A···H24Civ2.5000
C4···H16ii3.0800H22B···C11xii3.0900
C5···H16ii2.8500H22B···H11Bxii2.4800
C6···H11B2.9800H22B···H21C2.5400
C6···H16ii3.0500H22C···O1viii2.8300
C6···H11A2.6900H22C···O3iv2.6100
C7···H11A2.5400H22C···C1viii2.8800
C8···H21Ci2.8200H22C···H21B2.5300
C10···H32.9800H23A···O42.3800
C11···H22Bix3.0900H23B···O2vi2.7100
C11···H62.7800H23C···H52.4600
C11···H10Ai2.9500H23C···H24C2.2900
C12···H21Ai3.0300H24A···C183.0800
C13···H10Bv2.9500H24A···O2vi2.5600
C13···H3v3.0100H24B···C182.7900
C14···H22A2.4500H24B···C192.5300
C14···H3v2.8800H24C···H22Ai2.5000
C15···H22A2.5600H24C···H23C2.2900
C1—N1—C9119.8 (2)H12B—C12—H12C109.00
C1—N1—C10125.4 (2)N2—C12—H12A110.00
C9—N1—C10114.7 (2)N2—C12—H12B109.00
C8—N2—C11124.9 (2)N2—C12—H12C109.00
C8—N2—C12119.6 (3)H12A—C12—H12B109.00
C11—N2—C12115.6 (2)H12A—C12—H12C110.00
C13—N3—C22124.7 (2)O3—C13—N3123.2 (3)
C21—N3—C22115.2 (2)O3—C13—C14118.5 (2)
C13—N3—C21120.0 (2)N3—C13—C14118.2 (2)
C23—N4—C24116.3 (3)C13—C14—C15119.7 (2)
C20—N4—C23118.4 (3)C13—C14—C19120.5 (2)
C20—N4—C24124.2 (3)C15—C14—C19119.5 (3)
O1—C1—C2118.6 (2)C14—C15—C16120.7 (3)
O1—C1—N1123.9 (3)C15—C16—C17119.9 (3)
N1—C1—C2117.5 (2)C16—C17—C18120.0 (3)
C1—C2—C3119.7 (3)C17—C18—C19120.5 (2)
C1—C2—C7120.2 (2)C14—C19—C18119.4 (3)
C3—C2—C7119.8 (2)C14—C19—C20119.6 (2)
C2—C3—C4120.4 (3)C18—C19—C20120.6 (2)
C3—C4—C5120.0 (3)O4—C20—N4122.8 (3)
C4—C5—C6120.1 (3)O4—C20—C19118.4 (3)
C5—C6—C7120.2 (3)N4—C20—C19118.9 (3)
C6—C7—C8121.0 (3)C14—C15—H15120.00
C2—C7—C6119.4 (2)C16—C15—H15120.00
C2—C7—C8119.3 (2)C15—C16—H16120.00
N2—C8—C7118.2 (2)C17—C16—H16120.00
O2—C8—N2123.3 (3)C16—C17—H17120.00
O2—C8—C7118.5 (2)C18—C17—H17120.00
C2—C3—H3120.00C17—C18—H18120.00
C4—C3—H3120.00C19—C18—H18120.00
C3—C4—H4120.00N3—C21—H21A109.00
C5—C4—H4120.00N3—C21—H21B109.00
C6—C5—H5120.00N3—C21—H21C109.00
C4—C5—H5120.00H21A—C21—H21B110.00
C5—C6—H6120.00H21A—C21—H21C109.00
C7—C6—H6120.00H21B—C21—H21C110.00
N1—C9—H9B109.00N3—C22—H22A109.00
N1—C9—H9A109.00N3—C22—H22B109.00
H9A—C9—H9C109.00N3—C22—H22C109.00
N1—C9—H9C110.00H22A—C22—H22B109.00
H9A—C9—H9B109.00H22A—C22—H22C109.00
H9B—C9—H9C109.00H22B—C22—H22C109.00
N1—C10—H10C109.00N4—C23—H23A109.00
N1—C10—H10A109.00N4—C23—H23B109.00
N1—C10—H10B109.00N4—C23—H23C109.00
H10A—C10—H10C110.00H23A—C23—H23B110.00
H10B—C10—H10C109.00H23A—C23—H23C109.00
H10A—C10—H10B109.00H23B—C23—H23C110.00
H11A—C11—H11B109.00N4—C24—H24A109.00
H11A—C11—H11C109.00N4—C24—H24B109.00
N2—C11—H11A109.00N4—C24—H24C109.00
N2—C11—H11B110.00H24A—C24—H24B109.00
N2—C11—H11C109.00H24A—C24—H24C109.00
H11B—C11—H11C109.00H24B—C24—H24C109.00
C9—N1—C1—O13.8 (4)C3—C4—C5—C6−1.4 (4)
C10—N1—C1—O1−173.5 (3)C4—C5—C6—C70.7 (4)
C9—N1—C1—C2−172.2 (2)C5—C6—C7—C8175.2 (3)
C10—N1—C1—C210.5 (4)C5—C6—C7—C21.3 (4)
C12—N2—C8—C7−173.4 (2)C6—C7—C8—N255.4 (4)
C11—N2—C8—O2−177.3 (3)C2—C7—C8—O251.7 (4)
C12—N2—C8—O24.1 (4)C2—C7—C8—N2−130.7 (3)
C11—N2—C8—C75.2 (4)C6—C7—C8—O2−122.3 (3)
C21—N3—C13—O3−6.4 (4)O3—C13—C14—C19−58.4 (4)
C22—N3—C13—O3168.5 (3)N3—C13—C14—C15−60.6 (4)
C21—N3—C13—C14169.5 (2)N3—C13—C14—C19125.6 (3)
C22—N3—C13—C14−15.7 (4)O3—C13—C14—C15115.4 (3)
C23—N4—C20—O4−8.3 (4)C15—C14—C19—C181.0 (4)
C23—N4—C20—C19171.2 (3)C15—C14—C19—C20174.1 (3)
C24—N4—C20—C193.6 (4)C19—C14—C15—C16−0.7 (4)
C24—N4—C20—O4−175.9 (3)C13—C14—C19—C18174.9 (3)
O1—C1—C2—C3−114.6 (3)C13—C14—C15—C16−174.6 (3)
O1—C1—C2—C759.1 (4)C13—C14—C19—C20−12.1 (4)
N1—C1—C2—C361.6 (4)C14—C15—C16—C17−0.2 (5)
N1—C1—C2—C7−124.7 (3)C15—C16—C17—C180.8 (5)
C7—C2—C3—C42.0 (4)C16—C17—C18—C19−0.4 (4)
C1—C2—C7—C6−176.4 (3)C17—C18—C19—C14−0.5 (4)
C1—C2—C3—C4175.8 (3)C17—C18—C19—C20−173.4 (3)
C1—C2—C7—C89.5 (4)C14—C19—C20—N4119.4 (3)
C3—C2—C7—C6−2.7 (4)C18—C19—C20—O4111.9 (3)
C3—C2—C7—C8−176.7 (3)C18—C19—C20—N4−67.7 (4)
C2—C3—C4—C50.0 (4)C14—C19—C20—O4−61.1 (4)
D—H···AD—HH···AD···AD—H···A
C3—H3···O3vii0.932.603.518 (3)170
C5—H5···O4i0.932.583.141 (4)119
C6—H6···O4i0.932.513.105 (4)122
C18—H18···O2vi0.932.493.329 (3)150
C24—H24A···O2vi0.962.563.224 (4)127
C16—H16···Cg10.932.973.810 (4)124
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C3—H3⋯O3i 0.932.603.518 (3)170
C5—H5⋯O4ii 0.932.583.141 (4)119
C6—H6⋯O4ii 0.932.513.105 (4)122
C18—H18⋯O2iii 0.932.493.329 (3)150
C24—H24A⋯O2iii 0.962.563.224 (4)127
C16—H16⋯Cg10.932.973.810 (4)124

Symmetry codes: (i) ; (ii) ; (iii) .

  2 in total

1.  Absolute asymmetric synthesis by nucleophilic carbonyl addition using chiral crystals of achiral amides.

Authors:  Masami Sakamoto; Shuichiro Kobaru; Takashi Mino; Tsutomu Fujita
Journal:  Chem Commun (Camb)       Date:  2004-03-19       Impact factor: 6.222

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  2 in total
  1 in total

1.  4-Nitro-phthalamide.

Authors:  Chin Yee Jan; Norzianah Binti Haji Shamsudin; Ai Ling Tan; David J Young; Seik Weng Ng; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-02-15
  1 in total

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