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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2406–o2407.
Published online 2010 August 28. doi:  10.1107/S1600536810033817
PMCID: PMC3008041

Cyclo­hexane-1,3-diyl bis­(N-phenyl­carbamate)

Abstract

The asymmetric unit of the title compound, C20H22N2O4, comprises two crystallographically independent mol­ecules (A and B) with slightly different geometries. The dihedral angle between the two terminal phenyl rings is 61.7 (1)° in mol­ecule A and 29.6 (1)° in B. The cyclo­hexane rings adopt chair conformations. In the crystal packing, inter­molecular N—H(...)O hydrogen bonds inter­connect adjacent mol­ecules into a ladder-like structure along the c axis incorporating R 2 2(20) ring motifs. The crystal packing is further stabilized by weak inter­molecular C—H(...)π inter­actions.

Related literature

For general background and the synthesis of carbamates, see: Banerjee et al. (1978 [triangle]); Ghalib et al. (2010 [triangle]); Graia et al. (2009 [triangle]); Ibuka et al. (1985 [triangle]); Lapidus et al. (1987 [triangle]); Loev & Kormendy (1963 [triangle]); Niu et al. (2007 [triangle]). For ring conformation and puckering analysis, see: Cremer & Pople (1975 [triangle]). For graph-set motifs, see: Bernstein et al. (1995 [triangle]). For a related structure, see: Ghalib et al. (2010 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2406-scheme1.jpg

Experimental

Crystal data

  • C20H22N2O4
  • M r = 354.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2406-efi1.jpg
  • a = 38.356 (7) Å
  • b = 9.5453 (16) Å
  • c = 9.8472 (16) Å
  • β = 91.034 (3)°
  • V = 3604.7 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.55 × 0.15 × 0.13 mm

Data collection

  • Bruker APEXII DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.951, T max = 0.988
  • 30037 measured reflections
  • 10472 independent reflections
  • 6630 reflections with I > 2σ(I)
  • R int = 0.057

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.180
  • S = 1.08
  • 10472 reflections
  • 485 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033817/ci5161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033817/ci5161Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the University Grant (No. 1001/PTEKIND/8140152). HKF and JHG thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012). RMG and SHM thank USM for postdoctoral fellowships. JHG also thanks USM for a USM fellowship.

supplementary crystallographic information

Comment

Carbamates are a well-known class of organic compounds. They can be prepared by nickel-catalyzed coupling of CO2 and amines (Niu et al., 2007), by stirring of alcohols including steroids as well as primary and secondary alcohols, polyols, phenols with sodium cyanate and trifluoroacetic acid (Loev & Kormendy, 1963), by carbonylation of aromatic nitro compounds (Lapidus et al., 1987), by the reaction of isocyanates with alcohols in presence of Lewis acid (Ibuka et al., 1985) and by the reaction of an amine and an alcohol with phosgene. Phytosterol, β-sitosterol, stigmasterol, cholesterol, cyclohexanol and α-terpineol react with phenyl isocyanate to give carbamates (Banerjee et al., 1978; Graia et al., 2009; Ghalib et al., 2010). In the present work, the title compound has been synthesized by the reaction of cyclohexane-1,3-diol with phenylisocyanate in the presence of catalytic amount of HCl in chloroform solvent.

The asymmetric unit of the title compound comprises of two crystallographically independent molecules, designated A and B (Fig. 1). The orientation of the C1–C6 phenyl ring with respect to the rest of the molecule is different in A and B, as shown in the superposition of the non-H atoms of molecules A and B (Fig. 2) using XP in SHELXTL (Sheldrick, 2008); the r.m.s. deviation is 0.474 Å.

In each molecule, the cyclohexane ring (C8-C13) adopts a chair conformation; the puckering parameters are Q = 0.566 (2) Å, θ = 176.6 (2)°, [var phi] = 328 (4)° for molecule A and Q = 0.566 (2) Å, θ = 176.2 (2)°, [var phi] = 283 (4)° for molecule B. The dihedral angle between the C1–C6 and C15–C20 phenyl rings is 61.7 (1)° in molecule A and 29.6 (1)° in B. The geometric parameters are consistent with a related structure (Ghalib et al., 2010).

In the crystal packing, intermolecular N1A—H1NA···O1A, N2A—H2NA···O4A, N1B—H1NB···O1B, N2B—H2NB···O4B hydrogen bonds (Table 1) link adjacent molecules into one-dimensional chains incorporating R22(20) ring motifs (Bernstein et al., 1995) along the c axis (Fig. 3). Further stabilization of the crystal packing is provided by weak intermolecular C13A—H13B···Cg1 and C13B—H13C···Cg2 interactions (Table 1) where Cg1 and Cg2 are the centroids of C15A-C20A and C1B-C6B phenyl rings, respectively.

Experimental

A mixture of cyclohexane-1,3-diol (1.005 ml) and phenyl isocyanate (2.174 ml) in a 1:2 molar ratio was stirred in chloroform for 30 minutes in the presence of catalytic amount of HCl. The reaction mixture was dried with rota vapor at low pressure and then crystallized in a 1:1 mixture of chloroform and alcohol to afford colourless needle-like single crystals (yield: 2.60 g, m.p. 489.2 K). The melting point was taken using a Thermo Fisher digital melting point apparatus of IA9000 series and is uncorrected

Refinement

N-bound H atoms were located in a difference Fourier map and allowed refined freely [range of N—H = 0.83 (2)–0.92 (3) Å]. The remaining H atoms were placed in their calculated positions, with C–H = 0.93–0.98 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
Fig. 2.
Fit of molecule A (dashed lines) on molecule B (solid lines). H atoms have been omitted for clarity.
Fig. 3.
The crystal structure of the title compound, viewed along the b axis, showing molecular chains along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

Crystal data

C20H22N2O4F(000) = 1504
Mr = 354.40Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3229 reflections
a = 38.356 (7) Åθ = 3.0–32.1°
b = 9.5453 (16) ŵ = 0.09 mm1
c = 9.8472 (16) ÅT = 100 K
β = 91.034 (3)°Needle, colourless
V = 3604.7 (10) Å30.55 × 0.15 × 0.13 mm
Z = 8

Data collection

Bruker APEXII DUO CCD area-detector diffractometer10472 independent reflections
Radiation source: fine-focus sealed tube6630 reflections with I > 2σ(I)
graphiteRint = 0.057
[var phi] and ω scansθmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −51→53
Tmin = 0.951, Tmax = 0.988k = −11→13
30037 measured reflectionsl = −13→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0587P)2 + 2.1169P] where P = (Fo2 + 2Fc2)/3
10472 reflections(Δ/σ)max = 0.001
485 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
O1A0.32324 (4)0.22226 (16)0.31570 (14)0.0210 (3)
O2A0.35690 (3)0.27958 (16)0.49976 (14)0.0213 (3)
O3A0.47863 (3)0.24586 (16)0.53335 (14)0.0218 (3)
O4A0.51876 (4)0.22687 (17)0.36729 (14)0.0259 (3)
N1A0.30419 (4)0.19662 (19)0.53465 (18)0.0198 (4)
N2A0.53147 (4)0.17410 (19)0.59053 (17)0.0194 (4)
C1A0.25950 (5)0.0743 (2)0.3965 (2)0.0215 (4)
H1AA0.27600.04750.33350.026*
C2A0.22478 (6)0.0356 (2)0.3788 (2)0.0265 (5)
H2AA0.2180−0.01660.30310.032*
C3A0.20014 (6)0.0740 (3)0.4726 (2)0.0290 (5)
H3AA0.17690.04860.45940.035*
C4A0.21015 (6)0.1504 (3)0.5862 (2)0.0296 (5)
H4AA0.19370.17470.65010.036*
C5A0.24475 (5)0.1909 (2)0.6053 (2)0.0235 (4)
H5AA0.25140.24260.68160.028*
C6A0.26940 (5)0.1536 (2)0.5095 (2)0.0194 (4)
C7A0.32746 (5)0.2314 (2)0.4382 (2)0.0165 (4)
C8A0.38682 (5)0.3068 (2)0.4156 (2)0.0180 (4)
H8AA0.38480.25310.33100.022*
C9A0.38944 (5)0.4620 (2)0.3841 (2)0.0213 (4)
H9AA0.38750.51550.46730.026*
H9AB0.37040.48910.32350.026*
C10A0.42429 (5)0.4948 (2)0.3174 (2)0.0213 (4)
H10A0.42520.44810.23000.026*
H10B0.42600.59490.30170.026*
C11A0.45518 (5)0.4471 (2)0.4063 (2)0.0210 (4)
H11A0.47680.46620.36030.025*
H11B0.45540.49870.49120.025*
C12A0.45230 (5)0.2912 (2)0.4349 (2)0.0176 (4)
H12A0.45480.23830.35030.021*
C13A0.41781 (5)0.2548 (2)0.4998 (2)0.0172 (4)
H13A0.41710.29630.58970.021*
H13B0.41620.15390.51010.021*
C14A0.51069 (5)0.2170 (2)0.4859 (2)0.0180 (4)
C15A0.56754 (5)0.1433 (2)0.5863 (2)0.0179 (4)
C16A0.58223 (5)0.0713 (2)0.6959 (2)0.0206 (4)
H16A0.56810.04040.76560.025*
C17A0.61787 (6)0.0451 (2)0.7023 (2)0.0255 (5)
H17A0.6275−0.00200.77670.031*
C18A0.63918 (5)0.0888 (2)0.5979 (2)0.0259 (5)
H18A0.66310.07210.60220.031*
C19A0.62432 (5)0.1581 (2)0.4871 (2)0.0240 (5)
H19A0.63840.18580.41590.029*
C20A0.58872 (5)0.1867 (2)0.4809 (2)0.0195 (4)
H20A0.57910.23450.40690.023*
O1B−0.02136 (4)0.77244 (17)0.13203 (14)0.0242 (3)
O2B0.01910 (3)0.75338 (16)−0.03230 (14)0.0207 (3)
O3B0.14054 (3)0.71216 (15)0.00059 (14)0.0189 (3)
O4B0.17604 (4)0.74059 (17)0.18627 (14)0.0242 (3)
N1B−0.03341 (4)0.82633 (18)−0.09211 (17)0.0179 (3)
N2B0.19386 (4)0.78876 (19)−0.03047 (18)0.0184 (4)
C1B−0.09132 (5)0.8200 (2)0.0143 (2)0.0191 (4)
H1BA−0.08250.77050.08880.023*
C2B−0.12654 (5)0.8537 (2)0.0058 (2)0.0232 (4)
H2BA−0.14120.82700.07540.028*
C3B−0.14022 (5)0.9265 (2)−0.1049 (2)0.0243 (5)
H3BA−0.16390.9480−0.10990.029*
C4B−0.11823 (5)0.9667 (2)−0.2078 (2)0.0233 (4)
H4BA−0.12721.0157−0.28220.028*
C5B−0.08294 (5)0.9346 (2)−0.2011 (2)0.0195 (4)
H5BA−0.06840.9622−0.27070.023*
C6B−0.06928 (5)0.8607 (2)−0.08937 (19)0.0157 (4)
C7B−0.01295 (5)0.7830 (2)0.0140 (2)0.0172 (4)
C8B0.04525 (5)0.7077 (2)0.06741 (19)0.0165 (4)
H8BA0.04290.76170.15140.020*
C9B0.04178 (5)0.5521 (2)0.0974 (2)0.0184 (4)
H9BA0.04120.49980.01290.022*
H9BB0.02020.53480.14410.022*
C10B0.07256 (5)0.5031 (2)0.1857 (2)0.0192 (4)
H10C0.07030.40340.20290.023*
H10D0.07210.55120.27240.023*
C11B0.10739 (5)0.5314 (2)0.1179 (2)0.0194 (4)
H11C0.12640.50280.17800.023*
H11D0.10880.47740.03480.023*
C12B0.11062 (5)0.6861 (2)0.08605 (19)0.0160 (4)
H12B0.11300.73980.17060.019*
C13B0.07986 (5)0.7408 (2)0.0023 (2)0.0168 (4)
H13C0.08210.8415−0.00800.020*
H13D0.08030.6992−0.08750.020*
C14B0.17103 (5)0.7465 (2)0.0642 (2)0.0162 (4)
C15B0.22895 (5)0.8287 (2)−0.00429 (19)0.0178 (4)
C16B0.24314 (6)0.9297 (2)−0.0886 (2)0.0247 (5)
H16B0.22940.9715−0.15600.030*
C17B0.27798 (6)0.9682 (3)−0.0719 (3)0.0342 (6)
H17B0.28771.0338−0.12990.041*
C18B0.29811 (6)0.9090 (3)0.0306 (3)0.0374 (6)
H18B0.32120.93620.04280.045*
C19B0.28398 (6)0.8100 (3)0.1147 (3)0.0337 (6)
H19B0.29760.77080.18390.040*
C20B0.24941 (5)0.7677 (2)0.0972 (2)0.0251 (5)
H20B0.24010.69920.15320.030*
H1NA0.3111 (6)0.219 (2)0.612 (2)0.014 (6)*
H2NA0.5227 (7)0.181 (3)0.676 (3)0.048 (8)*
H1NB−0.0234 (7)0.824 (3)−0.177 (3)0.038 (7)*
H2NB0.1855 (6)0.795 (3)−0.114 (3)0.031 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0194 (7)0.0295 (8)0.0140 (7)−0.0001 (6)−0.0018 (5)0.0010 (6)
O2A0.0154 (6)0.0328 (8)0.0156 (7)−0.0043 (6)0.0008 (5)−0.0037 (6)
O3A0.0153 (6)0.0357 (9)0.0142 (7)0.0044 (6)−0.0003 (5)0.0007 (6)
O4A0.0215 (7)0.0415 (9)0.0147 (7)0.0057 (7)0.0007 (6)0.0019 (7)
N1A0.0174 (8)0.0301 (10)0.0118 (8)−0.0032 (7)−0.0010 (6)−0.0028 (7)
N2A0.0176 (8)0.0271 (9)0.0136 (8)0.0022 (7)−0.0005 (6)0.0017 (7)
C1A0.0207 (9)0.0231 (10)0.0206 (10)−0.0015 (8)−0.0035 (8)0.0004 (8)
C2A0.0260 (11)0.0282 (12)0.0251 (11)−0.0075 (9)−0.0090 (9)0.0016 (9)
C3A0.0187 (10)0.0334 (13)0.0346 (13)−0.0067 (9)−0.0050 (9)0.0081 (10)
C4A0.0204 (10)0.0326 (12)0.0361 (13)−0.0001 (9)0.0058 (9)0.0038 (10)
C5A0.0204 (10)0.0276 (11)0.0225 (11)−0.0009 (8)0.0020 (8)−0.0022 (9)
C6A0.0166 (9)0.0199 (10)0.0214 (10)−0.0024 (7)−0.0017 (8)0.0027 (8)
C7A0.0155 (9)0.0179 (9)0.0161 (10)0.0012 (7)−0.0032 (7)−0.0013 (7)
C8A0.0158 (8)0.0230 (10)0.0154 (9)−0.0015 (7)0.0021 (7)−0.0004 (8)
C9A0.0209 (9)0.0215 (10)0.0215 (10)0.0025 (8)−0.0017 (8)0.0009 (8)
C10A0.0281 (10)0.0168 (10)0.0190 (10)−0.0029 (8)−0.0010 (8)0.0000 (8)
C11A0.0204 (9)0.0241 (11)0.0185 (10)−0.0056 (8)0.0028 (8)−0.0012 (8)
C12A0.0157 (9)0.0240 (10)0.0131 (9)0.0014 (7)−0.0025 (7)−0.0007 (8)
C13A0.0169 (9)0.0204 (10)0.0143 (9)0.0000 (7)0.0014 (7)0.0019 (7)
C14A0.0157 (9)0.0222 (10)0.0161 (9)0.0010 (7)0.0006 (7)−0.0013 (8)
C15A0.0186 (9)0.0178 (9)0.0173 (10)0.0013 (7)−0.0015 (7)−0.0030 (8)
C16A0.0244 (10)0.0201 (10)0.0172 (10)0.0033 (8)−0.0023 (8)−0.0026 (8)
C17A0.0276 (11)0.0243 (11)0.0243 (11)0.0062 (9)−0.0076 (9)−0.0041 (9)
C18A0.0184 (10)0.0280 (12)0.0310 (12)0.0037 (8)−0.0049 (9)−0.0061 (10)
C19A0.0210 (10)0.0222 (11)0.0288 (12)0.0001 (8)0.0021 (8)−0.0021 (9)
C20A0.0205 (9)0.0199 (10)0.0181 (10)0.0015 (8)−0.0001 (8)0.0010 (8)
O1B0.0218 (7)0.0381 (9)0.0128 (7)0.0066 (6)−0.0001 (6)0.0021 (6)
O2B0.0144 (6)0.0333 (8)0.0145 (7)0.0035 (6)−0.0014 (5)0.0018 (6)
O3B0.0142 (6)0.0283 (8)0.0142 (7)−0.0040 (6)0.0004 (5)−0.0019 (6)
O4B0.0204 (7)0.0407 (9)0.0115 (7)−0.0029 (6)−0.0017 (5)0.0021 (6)
N1B0.0164 (8)0.0256 (9)0.0116 (8)0.0022 (7)0.0000 (6)0.0010 (7)
N2B0.0148 (7)0.0281 (9)0.0123 (8)−0.0021 (7)−0.0012 (6)0.0010 (7)
C1B0.0202 (9)0.0201 (10)0.0170 (10)0.0005 (8)−0.0010 (8)−0.0016 (8)
C2B0.0197 (9)0.0252 (11)0.0249 (11)0.0004 (8)0.0025 (8)−0.0029 (9)
C3B0.0178 (9)0.0238 (11)0.0312 (12)0.0037 (8)−0.0046 (8)−0.0030 (9)
C4B0.0252 (10)0.0210 (10)0.0233 (11)0.0038 (8)−0.0083 (8)−0.0021 (8)
C5B0.0244 (10)0.0196 (10)0.0145 (9)0.0019 (8)−0.0023 (8)0.0003 (8)
C6B0.0158 (8)0.0174 (9)0.0139 (9)0.0009 (7)−0.0028 (7)−0.0034 (7)
C7B0.0174 (9)0.0195 (10)0.0146 (9)0.0001 (7)−0.0002 (7)−0.0018 (8)
C8B0.0151 (8)0.0223 (10)0.0121 (9)0.0012 (7)−0.0020 (7)0.0001 (7)
C9B0.0174 (9)0.0223 (10)0.0154 (9)−0.0038 (7)−0.0008 (7)−0.0009 (8)
C10B0.0222 (9)0.0184 (10)0.0169 (10)−0.0032 (8)−0.0003 (8)0.0015 (8)
C11B0.0197 (9)0.0204 (10)0.0179 (10)0.0027 (8)−0.0010 (7)0.0017 (8)
C12B0.0136 (8)0.0210 (10)0.0134 (9)−0.0011 (7)0.0007 (7)0.0002 (7)
C13B0.0162 (9)0.0183 (10)0.0159 (10)−0.0013 (7)−0.0022 (7)0.0019 (7)
C14B0.0145 (8)0.0202 (10)0.0138 (9)0.0001 (7)−0.0002 (7)0.0001 (7)
C15B0.0163 (9)0.0235 (10)0.0137 (9)−0.0022 (8)0.0014 (7)−0.0048 (8)
C16B0.0256 (10)0.0243 (11)0.0242 (11)−0.0037 (9)0.0001 (8)0.0014 (9)
C17B0.0333 (12)0.0316 (13)0.0379 (14)−0.0133 (10)0.0046 (11)−0.0009 (11)
C18B0.0209 (11)0.0450 (15)0.0462 (16)−0.0111 (10)−0.0010 (10)−0.0063 (13)
C19B0.0217 (11)0.0485 (16)0.0306 (13)0.0002 (10)−0.0066 (9)−0.0002 (11)
C20B0.0181 (9)0.0359 (12)0.0212 (11)−0.0019 (9)−0.0020 (8)0.0044 (9)

Geometric parameters (Å, °)

O1A—C7A1.218 (2)O1B—C7B1.216 (2)
O2A—C7A1.352 (2)O2B—C7B1.349 (2)
O2A—C8A1.451 (2)O2B—C8B1.457 (2)
O3A—C14A1.352 (2)O3B—C14B1.357 (2)
O3A—C12A1.453 (2)O3B—C12B1.457 (2)
O4A—C14A1.218 (2)O4B—C14B1.215 (2)
N1A—C7A1.356 (2)N1B—C7B1.360 (3)
N1A—C6A1.414 (3)N1B—C6B1.415 (2)
N1A—H1NA0.83 (2)N1B—H1NB0.92 (3)
N2A—C14A1.354 (3)N2B—C14B1.352 (2)
N2A—C15A1.416 (2)N2B—C15B1.418 (2)
N2A—H2NA0.92 (3)N2B—H2NB0.88 (3)
C1A—C2A1.390 (3)C1B—C2B1.390 (3)
C1A—C6A1.392 (3)C1B—C6B1.393 (2)
C1A—H1AA0.93C1B—H1BA0.93
C2A—C3A1.383 (3)C2B—C3B1.387 (3)
C2A—H2AA0.93C2B—H2BA0.93
C3A—C4A1.383 (3)C3B—C4B1.384 (3)
C3A—H3AA0.93C3B—H3BA0.93
C4A—C5A1.392 (3)C4B—C5B1.388 (3)
C4A—H4AA0.93C4B—H4BA0.93
C5A—C6A1.394 (3)C5B—C6B1.400 (3)
C5A—H5AA0.93C5B—H5BA0.93
C8A—C9A1.517 (3)C8B—C13B1.518 (2)
C8A—C13A1.520 (3)C8B—C9B1.520 (3)
C8A—H8AA0.98C8B—H8BA0.98
C9A—C10A1.532 (3)C9B—C10B1.527 (3)
C9A—H9AA0.97C9B—H9BA0.97
C9A—H9AB0.97C9B—H9BB0.97
C10A—C11A1.530 (3)C10B—C11B1.528 (3)
C10A—H10A0.97C10B—H10C0.97
C10A—H10B0.97C10B—H10D0.97
C11A—C12A1.519 (3)C11B—C12B1.515 (3)
C11A—H11A0.97C11B—H11C0.97
C11A—H11B0.97C11B—H11D0.97
C12A—C13A1.520 (2)C12B—C13B1.520 (3)
C12A—H12A0.98C12B—H12B0.98
C13A—H13A0.97C13B—H13C0.97
C13A—H13B0.97C13B—H13D0.97
C15A—C16A1.390 (3)C15B—C20B1.388 (3)
C15A—C20A1.393 (3)C15B—C16B1.390 (3)
C16A—C17A1.390 (3)C16B—C17B1.393 (3)
C16A—H16A0.93C16B—H16B0.93
C17A—C18A1.389 (3)C17B—C18B1.381 (4)
C17A—H17A0.93C17B—H17B0.93
C18A—C19A1.390 (3)C18B—C19B1.375 (3)
C18A—H18A0.93C18B—H18B0.93
C19A—C20A1.393 (3)C19B—C20B1.394 (3)
C19A—H19A0.93C19B—H19B0.93
C20A—H20A0.93C20B—H20B0.93
C7A—O2A—C8A117.89 (15)C7B—O2B—C8B117.06 (14)
C14A—O3A—C12A117.13 (15)C14B—O3B—C12B117.12 (14)
C7A—N1A—C6A125.41 (18)C7B—N1B—C6B127.13 (16)
C7A—N1A—H1NA112.3 (15)C7B—N1B—H1NB116.4 (17)
C6A—N1A—H1NA121.2 (15)C6B—N1B—H1NB116.2 (17)
C14A—N2A—C15A127.07 (16)C14B—N2B—C15B125.39 (18)
C14A—N2A—H2NA117.3 (18)C14B—N2B—H2NB115.7 (16)
C15A—N2A—H2NA114.6 (18)C15B—N2B—H2NB118.8 (16)
C2A—C1A—C6A119.43 (19)C2B—C1B—C6B119.5 (2)
C2A—C1A—H1AA120.3C2B—C1B—H1BA120.2
C6A—C1A—H1AA120.3C6B—C1B—H1BA120.2
C3A—C2A—C1A120.7 (2)C3B—C2B—C1B121.13 (19)
C3A—C2A—H2AA119.6C3B—C2B—H2BA119.4
C1A—C2A—H2AA119.6C1B—C2B—H2BA119.4
C2A—C3A—C4A119.8 (2)C4B—C3B—C2B119.13 (19)
C2A—C3A—H3AA120.1C4B—C3B—H3BA120.4
C4A—C3A—H3AA120.1C2B—C3B—H3BA120.4
C3A—C4A—C5A120.4 (2)C3B—C4B—C5B120.7 (2)
C3A—C4A—H4AA119.8C3B—C4B—H4BA119.6
C5A—C4A—H4AA119.8C5B—C4B—H4BA119.6
C4A—C5A—C6A119.6 (2)C4B—C5B—C6B119.94 (18)
C4A—C5A—H5AA120.2C4B—C5B—H5BA120.0
C6A—C5A—H5AA120.2C6B—C5B—H5BA120.0
C1A—C6A—C5A120.07 (19)C1B—C6B—C5B119.55 (18)
C1A—C6A—N1A122.74 (18)C1B—C6B—N1B123.52 (18)
C5A—C6A—N1A117.16 (19)C5B—C6B—N1B116.87 (16)
O1A—C7A—O2A124.28 (17)O1B—C7B—O2B124.40 (19)
O1A—C7A—N1A126.79 (19)O1B—C7B—N1B126.90 (18)
O2A—C7A—N1A108.94 (17)O2B—C7B—N1B108.70 (15)
O2A—C8A—C9A110.34 (15)O2B—C8B—C13B104.44 (15)
O2A—C8A—C13A104.39 (15)O2B—C8B—C9B111.20 (16)
C9A—C8A—C13A112.13 (17)C13B—C8B—C9B111.45 (15)
O2A—C8A—H8AA110.0O2B—C8B—H8BA109.9
C9A—C8A—H8AA110.0C13B—C8B—H8BA109.9
C13A—C8A—H8AA110.0C9B—C8B—H8BA109.9
C8A—C9A—C10A110.43 (16)C8B—C9B—C10B109.91 (16)
C8A—C9A—H9AA109.6C8B—C9B—H9BA109.7
C10A—C9A—H9AA109.6C10B—C9B—H9BA109.7
C8A—C9A—H9AB109.6C8B—C9B—H9BB109.7
C10A—C9A—H9AB109.6C10B—C9B—H9BB109.7
H9AA—C9A—H9AB108.1H9BA—C9B—H9BB108.2
C11A—C10A—C9A111.48 (16)C9B—C10B—C11B111.69 (16)
C11A—C10A—H10A109.3C9B—C10B—H10C109.3
C9A—C10A—H10A109.3C11B—C10B—H10C109.3
C11A—C10A—H10B109.3C9B—C10B—H10D109.3
C9A—C10A—H10B109.3C11B—C10B—H10D109.3
H10A—C10A—H10B108.0H10C—C10B—H10D107.9
C12A—C11A—C10A109.87 (17)C12B—C11B—C10B109.78 (16)
C12A—C11A—H11A109.7C12B—C11B—H11C109.7
C10A—C11A—H11A109.7C10B—C11B—H11C109.7
C12A—C11A—H11B109.7C12B—C11B—H11D109.7
C10A—C11A—H11B109.7C10B—C11B—H11D109.7
H11A—C11A—H11B108.2H11C—C11B—H11D108.2
O3A—C12A—C11A111.31 (16)O3B—C12B—C11B110.74 (15)
O3A—C12A—C13A104.54 (15)O3B—C12B—C13B103.88 (14)
C11A—C12A—C13A111.63 (16)C11B—C12B—C13B112.44 (16)
O3A—C12A—H12A109.7O3B—C12B—H12B109.9
C11A—C12A—H12A109.7C11B—C12B—H12B109.9
C13A—C12A—H12A109.7C13B—C12B—H12B109.9
C12A—C13A—C8A111.94 (16)C8B—C13B—C12B112.05 (16)
C12A—C13A—H13A109.2C8B—C13B—H13C109.2
C8A—C13A—H13A109.2C12B—C13B—H13C109.2
C12A—C13A—H13B109.2C8B—C13B—H13D109.2
C8A—C13A—H13B109.2C12B—C13B—H13D109.2
H13A—C13A—H13B107.9H13C—C13B—H13D107.9
O4A—C14A—O3A124.35 (19)O4B—C14B—N2B127.10 (19)
O4A—C14A—N2A126.63 (18)O4B—C14B—O3B124.41 (16)
O3A—C14A—N2A109.01 (16)N2B—C14B—O3B108.48 (16)
C16A—C15A—C20A119.49 (18)C20B—C15B—C16B119.92 (19)
C16A—C15A—N2A117.55 (17)C20B—C15B—N2B122.74 (18)
C20A—C15A—N2A122.91 (19)C16B—C15B—N2B117.30 (19)
C17A—C16A—C15A120.56 (19)C15B—C16B—C17B119.9 (2)
C17A—C16A—H16A119.7C15B—C16B—H16B120.1
C15A—C16A—H16A119.7C17B—C16B—H16B120.1
C18A—C17A—C16A120.3 (2)C18B—C17B—C16B120.0 (2)
C18A—C17A—H17A119.9C18B—C17B—H17B120.0
C16A—C17A—H17A119.9C16B—C17B—H17B120.0
C17A—C18A—C19A119.06 (19)C19B—C18B—C17B120.0 (2)
C17A—C18A—H18A120.5C19B—C18B—H18B120.0
C19A—C18A—H18A120.5C17B—C18B—H18B120.0
C18A—C19A—C20A121.02 (19)C18B—C19B—C20B120.6 (2)
C18A—C19A—H19A119.5C18B—C19B—H19B119.7
C20A—C19A—H19A119.5C20B—C19B—H19B119.7
C15A—C20A—C19A119.6 (2)C15B—C20B—C19B119.5 (2)
C15A—C20A—H20A120.2C15B—C20B—H20B120.3
C19A—C20A—H20A120.2C19B—C20B—H20B120.3
C6A—C1A—C2A—C3A−0.6 (3)C6B—C1B—C2B—C3B0.5 (3)
C1A—C2A—C3A—C4A−0.7 (3)C1B—C2B—C3B—C4B−0.4 (3)
C2A—C3A—C4A—C5A1.2 (4)C2B—C3B—C4B—C5B0.1 (3)
C3A—C4A—C5A—C6A−0.3 (3)C3B—C4B—C5B—C6B0.1 (3)
C2A—C1A—C6A—C5A1.5 (3)C2B—C1B—C6B—C5B−0.3 (3)
C2A—C1A—C6A—N1A179.8 (2)C2B—C1B—C6B—N1B−177.38 (19)
C4A—C5A—C6A—C1A−1.1 (3)C4B—C5B—C6B—C1B0.0 (3)
C4A—C5A—C6A—N1A−179.5 (2)C4B—C5B—C6B—N1B177.30 (18)
C7A—N1A—C6A—C1A34.4 (3)C7B—N1B—C6B—C1B−18.0 (3)
C7A—N1A—C6A—C5A−147.2 (2)C7B—N1B—C6B—C5B164.83 (19)
C8A—O2A—C7A—O1A−7.5 (3)C8B—O2B—C7B—O1B−1.0 (3)
C8A—O2A—C7A—N1A172.67 (16)C8B—O2B—C7B—N1B178.74 (16)
C6A—N1A—C7A—O1A−5.5 (3)C6B—N1B—C7B—O1B−3.8 (3)
C6A—N1A—C7A—O2A174.33 (18)C6B—N1B—C7B—O2B176.52 (18)
C7A—O2A—C8A—C9A99.4 (2)C7B—O2B—C8B—C13B−157.19 (16)
C7A—O2A—C8A—C13A−139.95 (17)C7B—O2B—C8B—C9B82.5 (2)
O2A—C8A—C9A—C10A169.92 (16)O2B—C8B—C9B—C10B171.80 (14)
C13A—C8A—C9A—C10A54.0 (2)C13B—C8B—C9B—C10B55.7 (2)
C8A—C9A—C10A—C11A−56.4 (2)C8B—C9B—C10B—C11B−57.9 (2)
C9A—C10A—C11A—C12A57.4 (2)C9B—C10B—C11B—C12B57.0 (2)
C14A—O3A—C12A—C11A−83.1 (2)C14B—O3B—C12B—C11B−93.5 (2)
C14A—O3A—C12A—C13A156.25 (17)C14B—O3B—C12B—C13B145.54 (16)
C10A—C11A—C12A—O3A−172.51 (14)C10B—C11B—C12B—O3B−170.03 (15)
C10A—C11A—C12A—C13A−56.1 (2)C10B—C11B—C12B—C13B−54.3 (2)
O3A—C12A—C13A—C8A174.99 (15)O2B—C8B—C13B—C12B−174.04 (15)
C11A—C12A—C13A—C8A54.5 (2)C9B—C8B—C13B—C12B−53.9 (2)
O2A—C8A—C13A—C12A−172.95 (15)O3B—C12B—C13B—C8B173.31 (15)
C9A—C8A—C13A—C12A−53.5 (2)C11B—C12B—C13B—C8B53.5 (2)
C12A—O3A—C14A—O4A0.2 (3)C15B—N2B—C14B—O4B3.0 (3)
C12A—O3A—C14A—N2A−178.81 (16)C15B—N2B—C14B—O3B−177.74 (18)
C15A—N2A—C14A—O4A5.8 (4)C12B—O3B—C14B—O4B9.2 (3)
C15A—N2A—C14A—O3A−175.19 (18)C12B—O3B—C14B—N2B−170.07 (16)
C14A—N2A—C15A—C16A−165.8 (2)C14B—N2B—C15B—C20B33.7 (3)
C14A—N2A—C15A—C20A16.8 (3)C14B—N2B—C15B—C16B−148.7 (2)
C20A—C15A—C16A—C17A1.4 (3)C20B—C15B—C16B—C17B0.8 (3)
N2A—C15A—C16A—C17A−176.11 (19)N2B—C15B—C16B—C17B−176.9 (2)
C15A—C16A—C17A—C18A−1.0 (3)C15B—C16B—C17B—C18B−1.9 (4)
C16A—C17A—C18A—C19A−0.5 (3)C16B—C17B—C18B—C19B1.3 (4)
C17A—C18A—C19A—C20A1.5 (3)C17B—C18B—C19B—C20B0.3 (4)
C16A—C15A—C20A—C19A−0.4 (3)C16B—C15B—C20B—C19B0.8 (3)
N2A—C15A—C20A—C19A176.97 (19)N2B—C15B—C20B—C19B178.4 (2)
C18A—C19A—C20A—C15A−1.1 (3)C18B—C19B—C20B—C15B−1.4 (4)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C15A–C20A and C1B–C6B phenyl rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1Ai0.83 (2)2.13 (2)2.953 (2)174 (2)
N2A—H2NA···O4Ai0.91 (3)2.09 (3)2.934 (2)154 (2)
N1B—H1NB···O1Bii0.93 (3)2.10 (3)2.920 (2)147 (2)
N2B—H2NB···O4Bii0.88 (3)2.02 (3)2.874 (2)163 (3)
C13A—H13B···Cg1iii0.972.863.734 (2)151
C13B—H13C···Cg2iv0.972.863.732 (2)150

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y, −z+1; (iv) −x, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5161).

References

  • Banerjee, S., Dutta, S. & Chakraborti, S. K. (1978). J. Indian Chem. Soc.55, 284–286.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Ghalib, R. M., Sulaiman, O., Mehdi, S. H., Goh, J. H. & Fun, H.-K. (2010). Acta Cryst. E66, o1889–o1890. [PMC free article] [PubMed]
  • Graia, M., Raza Murad, G., Krimi Ammar, M., Mehdi, S. H. & Hashim, R. (2009). Acta Cryst. E65, o3231. [PMC free article] [PubMed]
  • Ibuka, T., Chu, G. N., Aoyagi, T., Kitada, K., Tsukida, T. & Yoneda, F. (1985). Chem. Pharm. Bull.33, 451–453.
  • Lapidus, A. L., Pirozhkov, S. D., Kapkin, V. D. & Krylova, A. Y. (1987). Org. Tech.13, 160.
  • Loev, B. & Kormendy, M. F. (1963). J. Org. Chem.28, 3421–3426.
  • Niu, D. F., Zhang, L., Xiao, L. P., Luo, Y. W. & Lu, J. X. (2007). Appl. Organomet. Chem.21, 941–944.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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